#------------------------------------------------------------------------------
#$Date: 2023-06-29 13:50:08 +0300 (Thu, 29 Jun 2023) $
#$Revision: 284613 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/32/7713267.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7713267
loop_
_publ_author_name
'Gruden, Evelin'
'Prinčič, Griša Grigorij'
'Hočevar, Jan'
'Iskra, Jernej'
'Kvíčala, Jaroslav'
'Tavčar, Gašper'
_publ_section_title
;
 From cyclic (alkyl)(amino)carbene (CAAC) precursors to fluorinating
 reagents. Experimental and theoretical study.
;
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_paper_doi               10.1039/d3dt01476b
_journal_year                    2023
_chemical_formula_moiety         '2(C20 H32 F N), C20 H32 N, F2 H'
_chemical_formula_sum            'C60 H97 F4 N3'
_chemical_formula_weight         936.40
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-04-11
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-05-16 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                96.869(3)
_cell_angle_beta                 96.961(3)
_cell_angle_gamma                93.453(3)
_cell_formula_units_Z            2
_cell_length_a                   9.3894(3)
_cell_length_b                   17.6755(7)
_cell_length_c                   17.8951(7)
_cell_measurement_reflns_used    7046
_cell_measurement_temperature    150.01(11)
_cell_measurement_theta_max      72.0660
_cell_measurement_theta_min      3.3470
_cell_volume                     2918.44(19)
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.6426
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  32.00   1.00   30.61    --  -40.98  58.00 -65.00   51
  2  ω   -112.00 -15.00   1.00   30.61    --  -40.98 -58.00 153.00   97
  3  ω     19.00  64.00   1.00   30.61    --   40.98  58.00 -65.00   45
  4  ω     -5.00  20.00   1.00   30.61    --   40.98 -58.00 153.00   25
  5  ω     76.00 174.00   1.00  122.43    --  103.58  58.00 -65.00   98
  6  ω     30.00  57.00   1.00  122.43    --  103.58 -58.00 153.00   27
  7  ω    -73.00  34.00   1.00   30.61    --  -40.98  77.00  30.00  107
  8  ω    -19.00  67.00   1.00   30.61    --   40.98 -77.00-120.00   86
  9  ω    -10.00  72.00   1.00   30.61    --   40.98 -77.00-180.00   82
 10  ω     44.00  74.00   1.00   30.61    --   40.98 -77.00  30.00   30
 11  ω     95.00 121.00   1.00  122.43    --  103.58  61.00 120.00   26
 12  ω     28.00 110.00   1.00  122.43    --  103.58 -80.00  70.42   82
 13  ω     33.00  60.00   1.00  122.43    --  103.58 -79.00 -60.58   27
 14  ω     77.00 105.00   1.00  122.43    --  103.58 -79.00-164.31   28
 15  ω    103.00 175.00   1.00  122.43    --  103.58  77.00   0.00   72
 16  ω    111.00 163.00   1.00  122.43    --  103.58  77.00  30.00   52
 17  ω     27.00  60.00   1.00  122.43    --  103.58 -79.00-164.31   33
 18  ω    131.00 161.00   1.00  122.43    --  103.58  61.00 120.00   30
 19  ω     89.00 122.00   1.00  122.43    --  103.58 -80.00  34.51   33
 20  ω     68.00 108.00   1.00  122.43    --  103.58 -80.00-101.19   40
 21  ω     36.00 136.00   1.00  122.43    --  103.58 -80.00 152.42  100
 22  ω    106.00 142.00   1.00  122.43    --  103.58  77.00 150.00   36
 23  ω     79.00 136.00   1.00  122.43    --  103.58 -79.00 -60.58   57
 24  ω    105.00 178.00   1.00  122.43    --  103.58  77.00-120.00   73
 25  ω     75.00 102.00   1.00  122.43    --  103.58 -80.00  21.66   27
 26  ω    122.00 149.00   1.00  122.43    --  103.58  77.00-150.00   27
 27  ω     31.00 122.00   1.00  122.43    --  103.58 -45.00 -60.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11761
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         72.552
_diffrn_reflns_theta_min         3.324
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.066
_exptl_crystal_description       block
_exptl_crystal_F_000             1028
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile and t-BuOH'
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.121
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     702
_refine_ls_number_reflns         11761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0982P)²+0.0761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1600
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8607
_reflns_number_total             11761
_reflns_threshold_expression     'I > 2σ(I)'
_twin_special_details
;
Component 2 rotated by 179.8280° 
around [0.00 1.00 0.00] (reciprocal) or [0.14 0.98 0.13] (direct)
;
_cod_data_source_file            d3dt01476b2.cif
_cod_data_source_block           exp_1438_caachf_tbuoh_mecn_twin1_hklf4
_cod_original_cell_volume        2918.4(2)
_cod_database_code               7713267
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7935(10)
 0.2065(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All F(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C47B) = Uanis(C47A)
Uanis(C44B) = Uanis(C44A)
4. Others
 Sof(F21B)=Sof(H22A)=1-FVAR(1)
 Sof(F21A)=Sof(H22)=FVAR(1)
 Sof(F41B)=Sof(H42A)=1-FVAR(2)
 Sof(F41A)=Sof(H42)=FVAR(2)
 Sof(C26B)=Sof(H26D)=Sof(H26E)=Sof(H26F)=Sof(C27B)=Sof(H27D)=Sof(H27E)=
 Sof(H27F)=1-FVAR(3)
 Sof(C26A)=Sof(H26A)=Sof(H26B)=Sof(H26C)=Sof(C27A)=Sof(H27A)=Sof(H27B)=
 Sof(H27C)=FVAR(3)
 Sof(C24B)=Sof(H24C)=Sof(H24D)=1-FVAR(4)
 Sof(C24A)=Sof(H24A)=Sof(H24B)=FVAR(4)
 Sof(C46B)=Sof(H46D)=Sof(H46E)=Sof(H46F)=Sof(C47B)=Sof(H47D)=Sof(H47E)=
 Sof(H47F)=1-FVAR(5)
 Sof(C46A)=Sof(H46A)=Sof(H46B)=Sof(H46C)=Sof(C47A)=Sof(H47A)=Sof(H47B)=
 Sof(H47C)=FVAR(5)
 Sof(C44B)=Sof(H44C)=Sof(H44D)=1-FVAR(6)
 Sof(C44A)=Sof(H44A)=Sof(H44B)=FVAR(6)
5.a Ternary CH refined with riding coordinates:
 C22(H22), C22(H22A), C36(H36), C39(H39), C42(H42), C42(H42A), C56(H56),
 C59(H59), C16(H16), C19(H19)
5.b Secondary CH2 refined with riding coordinates:
 C24A(H24A,H24B), C24B(H24C,H24D), C44A(H44A,H44B), C44B(H44C,H44D), C4(H4A,H4B)
5.c Aromatic/amide H refined with riding coordinates:
 C32(H32), C33(H33), C34(H34), C52(H52), C53(H53), C54(H54), C2(H2), C12(H12),
 C13(H13), C14(H14)
5.d Idealised Me refined as rotating group:
 C26A(H26A,H26B,H26C), C26B(H26D,H26E,H26F), C27A(H27A,H27B,H27C), C27B(H27D,
 H27E,H27F), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C37(H37A,H37B,H37C),
 C38(H38A,H38B,H38C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C46A(H46A,H46B,
 H46C), C46B(H46D,H46E,H46F), C47A(H47A,H47B,H47C), C47B(H47D,H47E,H47F),
 C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C57(H57A,H57B,H57C), C58(H58A,H58B,
 H58C), C60(H60A,H60B,H60C), C61(H61A,H61B,H61C), C6(H6A,H6B,H6C), C7(H7A,H7B,
 H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F21A F 0.5184(3) 0.31958(14) 0.76718(17) 0.0758(10) Uani 0.674(5) 1 d . . P A 1
F21B F 0.6839(9) 0.3047(4) 0.7277(4) 0.108(3) Uani 0.326(5) 1 d . . P A 2
N21 N 0.59257(19) 0.19451(10) 0.77430(11) 0.0403(4) Uani 1 1 d . . . . .
C22 C 0.6278(3) 0.27454(14) 0.78318(15) 0.0524(6) Uani 1 1 d . . . . .
H22 H 0.696978 0.283056 0.746177 0.063 Uiso 0.674(5) 1 calc R U P A 1
H22A H 0.534569 0.298380 0.787053 0.063 Uiso 0.326(5) 1 calc R U P A 2
C23 C 0.7149(3) 0.29368(14) 0.86223(16) 0.0560(6) Uani 1 1 d . . . . .
C24A C 0.7807(7) 0.2189(2) 0.8756(3) 0.0477(17) Uani 0.618(15) 1 d . . P B 1
H24A H 0.794570 0.213866 0.930448 0.057 Uiso 0.618(15) 1 calc R U P B 1
H24B H 0.875198 0.217096 0.856429 0.057 Uiso 0.618(15) 1 calc R U P B 1
C24B C 0.7083(14) 0.2215(5) 0.8987(5) 0.056(3) Uani 0.382(15) 1 d . . P B 2
H24C H 0.632385 0.222289 0.932585 0.067 Uiso 0.382(15) 1 calc R U P B 2
H24D H 0.801643 0.215828 0.929006 0.067 Uiso 0.382(15) 1 calc R U P B 2
C25 C 0.6728(3) 0.15356(14) 0.83151(15) 0.0523(6) Uani 1 1 d . . . . .
C26A C 0.8269(7) 0.3615(3) 0.8698(4) 0.099(3) Uani 0.662(8) 1 d . . P B 1
H26A H 0.907818 0.346437 0.842910 0.148 Uiso 0.662(8) 1 calc R U P B 1
H26B H 0.861681 0.377467 0.923537 0.148 Uiso 0.662(8) 1 calc R U P B 1
H26C H 0.783122 0.404027 0.847629 0.148 Uiso 0.662(8) 1 calc R U P B 1
C26B C 0.8701(10) 0.3084(7) 0.8363(6) 0.078(4) Uani 0.338(8) 1 d . . P B 2
H26D H 0.889572 0.264589 0.801019 0.117 Uiso 0.338(8) 1 calc R U P B 2
H26E H 0.943435 0.314957 0.880970 0.117 Uiso 0.338(8) 1 calc R U P B 2
H26F H 0.872451 0.354640 0.811156 0.117 Uiso 0.338(8) 1 calc R U P B 2
C27A C 0.6040(7) 0.3121(4) 0.9184(3) 0.087(2) Uani 0.662(8) 1 d . . P B 1
H27A H 0.575439 0.364247 0.915539 0.130 Uiso 0.662(8) 1 calc R U P B 1
H27B H 0.647603 0.307931 0.970222 0.130 Uiso 0.662(8) 1 calc R U P B 1
H27C H 0.518990 0.275890 0.904943 0.130 Uiso 0.662(8) 1 calc R U P B 1
C27B C 0.6870(11) 0.3657(6) 0.9102(6) 0.069(3) Uani 0.338(8) 1 d . . P B 2
H27D H 0.704905 0.409669 0.883230 0.104 Uiso 0.338(8) 1 calc R U P B 2
H27E H 0.751265 0.371499 0.958326 0.104 Uiso 0.338(8) 1 calc R U P B 2
H27F H 0.586781 0.362772 0.920444 0.104 Uiso 0.338(8) 1 calc R U P B 2
C28 C 0.5730(4) 0.1069(2) 0.8718(2) 0.0831(10) Uani 1 1 d . . . . .
H28A H 0.511340 0.140774 0.898365 0.125 Uiso 1 1 calc R U . . .
H28B H 0.630070 0.080274 0.908642 0.125 Uiso 1 1 calc R U . . .
H28C H 0.513018 0.069282 0.834598 0.125 Uiso 1 1 calc R U . . .
C29 C 0.7739(4) 0.0977(2) 0.7983(2) 0.0846(10) Uani 1 1 d . . . . .
H29A H 0.717596 0.057541 0.762367 0.127 Uiso 1 1 calc R U . . .
H29B H 0.826915 0.074677 0.839302 0.127 Uiso 1 1 calc R U . . .
H29C H 0.842092 0.125214 0.771817 0.127 Uiso 1 1 calc R U . . .
C30 C 0.5097(2) 0.15595(12) 0.70633(12) 0.0383(5) Uani 1 1 d . . . . .
C31 C 0.5726(3) 0.13827(13) 0.63950(14) 0.0456(5) Uani 1 1 d . . . . .
C32 C 0.4883(3) 0.09946(16) 0.57526(15) 0.0563(6) Uani 1 1 d . . . . .
H32 H 0.531177 0.086703 0.530428 0.068 Uiso 1 1 calc R U . . .
C33 C 0.3445(3) 0.07921(16) 0.57526(16) 0.0582(7) Uani 1 1 d . . . . .
H33 H 0.289203 0.052252 0.531088 0.070 Uiso 1 1 calc R U . . .
C34 C 0.2814(3) 0.09839(14) 0.64001(15) 0.0503(6) Uani 1 1 d . . . . .
H34 H 0.181871 0.084756 0.639828 0.060 Uiso 1 1 calc R U . . .
C35 C 0.3608(2) 0.13738(12) 0.70563(13) 0.0414(5) Uani 1 1 d . . . . .
C36 C 0.7275(3) 0.16415(16) 0.63296(17) 0.0561(6) Uani 1 1 d . . . . .
H36 H 0.776223 0.184487 0.684913 0.067 Uiso 1 1 calc R U . . .
C37 C 0.7280(4) 0.2291(2) 0.5838(2) 0.0935(12) Uani 1 1 d . . . . .
H37A H 0.678294 0.210710 0.532926 0.140 Uiso 1 1 calc R U . . .
H37B H 0.827559 0.246820 0.580111 0.140 Uiso 1 1 calc R U . . .
H37C H 0.678563 0.271464 0.606822 0.140 Uiso 1 1 calc R U . . .
C38 C 0.8114(3) 0.0981(2) 0.6009(2) 0.0839(10) Uani 1 1 d . . . . .
H38A H 0.810725 0.057563 0.633768 0.126 Uiso 1 1 calc R U . . .
H38B H 0.910969 0.117005 0.598839 0.126 Uiso 1 1 calc R U . . .
H38C H 0.765956 0.077668 0.549658 0.126 Uiso 1 1 calc R U . . .
C39 C 0.2808(3) 0.16292(13) 0.77208(14) 0.0461(5) Uani 1 1 d . . . . .
H39 H 0.353293 0.186119 0.815615 0.055 Uiso 1 1 calc R U . . .
C40 C 0.1805(3) 0.22414(15) 0.75103(17) 0.0586(7) Uani 1 1 d . . . . .
H40A H 0.235755 0.266013 0.733717 0.088 Uiso 1 1 calc R U . . .
H40B H 0.136277 0.243858 0.795569 0.088 Uiso 1 1 calc R U . . .
H40C H 0.105131 0.201829 0.710284 0.088 Uiso 1 1 calc R U . . .
C41 C 0.1954(3) 0.09653(16) 0.79792(18) 0.0634(7) Uani 1 1 d . . . . .
H41A H 0.123183 0.073065 0.756105 0.095 Uiso 1 1 calc R U . . .
H41B H 0.147268 0.115639 0.841256 0.095 Uiso 1 1 calc R U . . .
H41C H 0.260999 0.058356 0.812934 0.095 Uiso 1 1 calc R U . . .
F41A F 0.8107(3) 0.70071(15) 0.80719(16) 0.0617(10) Uani 0.566(5) 1 d . . P C 1
F41B F 0.6247(5) 0.6926(2) 0.8365(3) 0.0926(18) Uani 0.434(5) 1 d . . P C 2
N41 N 0.73116(18) 0.81676(10) 0.86424(10) 0.0386(4) Uani 1 1 d . . . . .
C42 C 0.7398(3) 0.73663(13) 0.86222(14) 0.0448(5) Uani 1 1 d . . . . .
H42 H 0.639386 0.712326 0.855446 0.054 Uiso 0.566(5) 1 calc R U P C 1
H42A H 0.812111 0.722695 0.827197 0.054 Uiso 0.434(5) 1 calc R U P C 2
C43 C 0.8107(3) 0.72594(16) 0.94228(16) 0.0626(7) Uani 1 1 d . . . . .
C44A C 0.9018(5) 0.80181(19) 0.9670(2) 0.0558(10) Uani 0.835(8) 1 d . . P D 1
H44A H 0.911546 0.814659 1.022848 0.067 Uiso 0.835(8) 1 calc R U P D 1
H44B H 0.999111 0.797963 0.951590 0.067 Uiso 0.835(8) 1 calc R U P D 1
C44B C 0.831(2) 0.7966(10) 0.9847(11) 0.0558(10) Uani 0.165(8) 1 d . . P D 2
H44C H 0.925537 0.801555 1.016822 0.067 Uiso 0.165(8) 1 calc R U P D 2
H44D H 0.755232 0.802569 1.018429 0.067 Uiso 0.165(8) 1 calc R U P D 2
C45 C 0.8250(3) 0.86323(14) 0.92837(14) 0.0483(6) Uani 1 1 d . . . . .
C46A C 0.8954(7) 0.6570(3) 0.9459(3) 0.098(2) Uani 0.846(6) 1 d . . P D 1
H46A H 0.931799 0.653087 0.998870 0.146 Uiso 0.846(6) 1 calc R U P D 1
H46B H 0.976427 0.661629 0.916598 0.146 Uiso 0.846(6) 1 calc R U P D 1
H46C H 0.833190 0.611022 0.924548 0.146 Uiso 0.846(6) 1 calc R U P D 1
C46B C 0.9782(18) 0.6991(17) 0.9108(12) 0.074(8) Uani 0.154(6) 1 d . . P D 2
H46D H 0.966464 0.645922 0.886648 0.111 Uiso 0.154(6) 1 calc R U P D 2
H46E H 1.053503 0.704253 0.954424 0.111 Uiso 0.154(6) 1 calc R U P D 2
H46F H 1.005470 0.732497 0.874087 0.111 Uiso 0.154(6) 1 calc R U P D 2
C47A C 0.6879(5) 0.7176(2) 0.9938(2) 0.0776(12) Uani 0.846(6) 1 d . . P D 1
H47A H 0.622672 0.758305 0.987537 0.116 Uiso 0.846(6) 1 calc R U P D 1
H47B H 0.730391 0.721580 1.047027 0.116 Uiso 0.846(6) 1 calc R U P D 1
H47C H 0.634025 0.667777 0.978900 0.116 Uiso 0.846(6) 1 calc R U P D 1
C47B C 0.768(3) 0.6556(13) 0.9681(12) 0.0776(12) Uani 0.154(6) 1 d . . P D 2
H47D H 0.666266 0.655514 0.976313 0.116 Uiso 0.154(6) 1 calc R U P D 2
H47E H 0.827055 0.650304 1.015815 0.116 Uiso 0.154(6) 1 calc R U P D 2
H47F H 0.779812 0.612832 0.929779 0.116 Uiso 0.154(6) 1 calc R U P D 2
C48 C 0.9414(3) 0.91498(19) 0.9031(2) 0.0756(9) Uani 1 1 d . . . . .
H48A H 1.000989 0.883870 0.872147 0.113 Uiso 1 1 calc R U . . .
H48B H 1.001850 0.942265 0.947816 0.113 Uiso 1 1 calc R U . . .
H48C H 0.896121 0.951979 0.872995 0.113 Uiso 1 1 calc R U . . .
C49 C 0.7379(3) 0.91478(16) 0.97770(16) 0.0571(7) Uani 1 1 d . . . . .
H49A H 0.689601 0.950353 0.946939 0.086 Uiso 1 1 calc R U . . .
H49B H 0.802606 0.943700 1.019917 0.086 Uiso 1 1 calc R U . . .
H49C H 0.665703 0.883241 0.997786 0.086 Uiso 1 1 calc R U . . .
C50 C 0.6534(2) 0.84927(11) 0.80352(12) 0.0348(4) Uani 1 1 d . . . . .
C51 C 0.7164(2) 0.86372(11) 0.73874(13) 0.0384(5) Uani 1 1 d . . . . .
C52 C 0.6380(2) 0.89821(13) 0.68228(14) 0.0440(5) Uani 1 1 d . . . . .
H52 H 0.681133 0.908383 0.638813 0.053 Uiso 1 1 calc R U . . .
C53 C 0.4991(2) 0.91786(13) 0.68828(14) 0.0451(5) Uani 1 1 d . . . . .
H53 H 0.448228 0.942633 0.650160 0.054 Uiso 1 1 calc R U . . .
C54 C 0.4357(2) 0.90104(12) 0.75010(13) 0.0408(5) Uani 1 1 d . . . . .
H54 H 0.339617 0.913575 0.753670 0.049 Uiso 1 1 calc R U . . .
C55 C 0.5083(2) 0.86605(11) 0.80796(12) 0.0360(4) Uani 1 1 d . . . . .
C56 C 0.8655(2) 0.84011(13) 0.72433(15) 0.0457(5) Uani 1 1 d . . . . .
H56 H 0.911416 0.820637 0.770969 0.055 Uiso 1 1 calc R U . . .
C57 C 0.8521(3) 0.77551(16) 0.65880(16) 0.0577(7) Uani 1 1 d . . . . .
H57A H 0.797300 0.731092 0.671893 0.087 Uiso 1 1 calc R U . . .
H57B H 0.948244 0.761475 0.649239 0.087 Uiso 1 1 calc R U . . .
H57C H 0.802043 0.792414 0.613124 0.087 Uiso 1 1 calc R U . . .
C58 C 0.9636(3) 0.90688(17) 0.7078(2) 0.0669(8) Uani 1 1 d . . . . .
H58A H 0.925134 0.923837 0.659684 0.100 Uiso 1 1 calc R U . . .
H58B H 1.060517 0.890281 0.704217 0.100 Uiso 1 1 calc R U . . .
H58C H 0.967814 0.949250 0.748864 0.100 Uiso 1 1 calc R U . . .
C59 C 0.4262(2) 0.84322(13) 0.87099(13) 0.0419(5) Uani 1 1 d . . . . .
H59 H 0.496150 0.824277 0.909926 0.050 Uiso 1 1 calc R U . . .
C60 C 0.3120(3) 0.77813(15) 0.84008(16) 0.0536(6) Uani 1 1 d . . . . .
H60A H 0.239691 0.796092 0.803422 0.080 Uiso 1 1 calc R U . . .
H60B H 0.265591 0.761185 0.882024 0.080 Uiso 1 1 calc R U . . .
H60C H 0.357564 0.735354 0.814984 0.080 Uiso 1 1 calc R U . . .
C61 C 0.3560(3) 0.91085(15) 0.91033(15) 0.0526(6) Uani 1 1 d . . . . .
H61A H 0.430346 0.951685 0.931371 0.079 Uiso 1 1 calc R U . . .
H61B H 0.306876 0.893885 0.951365 0.079 Uiso 1 1 calc R U . . .
H61C H 0.286125 0.930069 0.873305 0.079 Uiso 1 1 calc R U . . .
N1 N 0.22827(17) 0.50701(10) 0.68831(9) 0.0347(4) Uani 1 1 d . . . . .
C2 C 0.3219(2) 0.49573(11) 0.74290(12) 0.0363(4) Uani 1 1 d . . . . .
H2 H 0.417539 0.484626 0.736004 0.044 Uiso 1 1 calc R U . . .
C3 C 0.2690(2) 0.50139(13) 0.81819(12) 0.0424(5) Uani 1 1 d . . . . .
C4 C 0.1219(3) 0.53455(15) 0.80004(14) 0.0516(6) Uani 1 1 d . . . . .
H4A H 0.048597 0.509679 0.826365 0.062 Uiso 1 1 calc R U . . .
H4B H 0.129380 0.590171 0.817223 0.062 Uiso 1 1 calc R U . . .
C5 C 0.0790(2) 0.51921(13) 0.71369(13) 0.0432(5) Uani 1 1 d . . . . .
C6 C 0.2574(3) 0.42282(16) 0.84509(17) 0.0612(7) Uani 1 1 d . . . . .
H6A H 0.184300 0.389485 0.810639 0.092 Uiso 1 1 calc R U . . .
H6B H 0.229960 0.427957 0.896475 0.092 Uiso 1 1 calc R U . . .
H6C H 0.350538 0.400546 0.845451 0.092 Uiso 1 1 calc R U . . .
C7 C 0.3753(3) 0.55559(18) 0.87593(16) 0.0671(8) Uani 1 1 d . . . . .
H7A H 0.467808 0.532905 0.883361 0.101 Uiso 1 1 calc R U . . .
H7B H 0.336394 0.563518 0.924447 0.101 Uiso 1 1 calc R U . . .
H7C H 0.389072 0.604774 0.856668 0.101 Uiso 1 1 calc R U . . .
C8 C 0.0126(3) 0.58685(15) 0.68177(16) 0.0539(6) Uani 1 1 d . . . . .
H8A H 0.073025 0.633767 0.701656 0.081 Uiso 1 1 calc R U . . .
H8B H -0.083833 0.591268 0.696800 0.081 Uiso 1 1 calc R U . . .
H8C H 0.005735 0.579106 0.626261 0.081 Uiso 1 1 calc R U . . .
C9 C -0.0185(2) 0.44704(15) 0.68537(15) 0.0508(6) Uani 1 1 d . . . . .
H9A H -0.111584 0.451902 0.704286 0.076 Uiso 1 1 calc R U . . .
H9B H 0.026331 0.402961 0.703830 0.076 Uiso 1 1 calc R U . . .
H9C H -0.032890 0.439757 0.629742 0.076 Uiso 1 1 calc R U . . .
C10 C 0.25873(19) 0.50760(12) 0.61005(11) 0.0338(4) Uani 1 1 d . . . . .
C11 C 0.2499(2) 0.43840(12) 0.56212(12) 0.0367(5) Uani 1 1 d . . . . .
C12 C 0.2751(2) 0.44358(14) 0.48685(12) 0.0410(5) Uani 1 1 d . . . . .
H12 H 0.268085 0.398212 0.451875 0.049 Uiso 1 1 calc R U . . .
C13 C 0.3095(2) 0.51213(14) 0.46271(13) 0.0450(5) Uani 1 1 d . . . . .
H13 H 0.324289 0.513893 0.411336 0.054 Uiso 1 1 calc R U . . .
C14 C 0.3228(2) 0.57890(14) 0.51275(13) 0.0424(5) Uani 1 1 d . . . . .
H14 H 0.348299 0.626063 0.495523 0.051 Uiso 1 1 calc R U . . .
C15 C 0.2994(2) 0.57798(12) 0.58830(12) 0.0372(5) Uani 1 1 d . . . . .
C16 C 0.2285(2) 0.36033(12) 0.58717(13) 0.0428(5) Uani 1 1 d . . . . .
H16 H 0.209674 0.367523 0.641289 0.051 Uiso 1 1 calc R U . . .
C17 C 0.3663(3) 0.31819(14) 0.58326(16) 0.0529(6) Uani 1 1 d . . . . .
H17A H 0.384144 0.308125 0.530290 0.079 Uiso 1 1 calc R U . . .
H17B H 0.354757 0.269681 0.604064 0.079 Uiso 1 1 calc R U . . .
H17C H 0.447775 0.349884 0.612944 0.079 Uiso 1 1 calc R U . . .
C18 C 0.0997(3) 0.31192(16) 0.54007(18) 0.0633(7) Uani 1 1 d . . . . .
H18A H 0.012006 0.338687 0.544253 0.095 Uiso 1 1 calc R U . . .
H18B H 0.088706 0.262465 0.559151 0.095 Uiso 1 1 calc R U . . .
H18C H 0.116149 0.303734 0.486758 0.095 Uiso 1 1 calc R U . . .
C19 C 0.3334(2) 0.65129(13) 0.64345(13) 0.0417(5) Uani 1 1 d . . . . .
H19 H 0.297273 0.642357 0.692219 0.050 Uiso 1 1 calc R U . . .
C20 C 0.2618(4) 0.71966(15) 0.61535(16) 0.0626(7) Uani 1 1 d . . . . .
H20A H 0.305784 0.734305 0.571722 0.094 Uiso 1 1 calc R U . . .
H20B H 0.274846 0.762672 0.656148 0.094 Uiso 1 1 calc R U . . .
H20C H 0.158824 0.705936 0.600112 0.094 Uiso 1 1 calc R U . . .
C21 C 0.4965(3) 0.66876(18) 0.65976(18) 0.0670(8) Uani 1 1 d . . . . .
H21A H 0.541156 0.624484 0.677865 0.100 Uiso 1 1 calc R U . . .
H21B H 0.518751 0.713196 0.698717 0.100 Uiso 1 1 calc R U . . .
H21C H 0.534139 0.679801 0.613162 0.100 Uiso 1 1 calc R U . . .
F1 F 0.61334(15) 0.44753(9) 0.71678(10) 0.0626(4) Uani 1 1 d . . . . .
H1 H 0.667(4) 0.502(2) 0.758(2) 0.094 Uiso 1 1 d . U . . .
F2 F 0.7294(2) 0.55188(12) 0.78556(14) 0.0999(7) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 8 7 0.0932
6 -2 -3 0.1314
6 0 -1 0.1327
-6 4 4 0.1426
0 9 -8 0.0686
0 -8 9 0.0434
-1 -11 2 0.0727
1 -11 -1 0.0802
0 -2 2 0.0619
0 2 -2 0.0891
1 -2 2 0.1131
1 -1 1 0.1304
2 -3 1 0.1242
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 N21 C25 114.66(18) . . ?
C22 N21 C30 121.14(19) . . ?
C30 N21 C25 122.92(17) . . ?
F21A C22 N21 117.0(2) . . ?
F21A C22 H22 105.8 . . ?
F21A C22 C23 115.9(2) . . ?
F21B C22 N21 118.6(4) . . ?
F21B C22 H22A 105.5 . . ?
F21B C22 C23 115.3(4) . . ?
N21 C22 H22 105.8 . . ?
N21 C22 H22A 105.5 . . ?
N21 C22 C23 105.4(2) . . ?
C23 C22 H22 105.8 . . ?
C23 C22 H22A 105.5 . . ?
C22 C23 C26B 98.3(4) . . ?
C22 C23 C27A 106.3(3) . . ?
C24A C23 C22 103.2(2) . . ?
C24A C23 C26A 113.2(4) . . ?
C24A C23 C27A 110.4(4) . . ?
C24B C23 C22 106.1(3) . . ?
C24B C23 C26B 110.0(8) . . ?
C26A C23 C22 114.5(3) . . ?
C26A C23 C27A 109.0(4) . . ?
C27B C23 C22 118.0(4) . . ?
C27B C23 C24B 116.4(6) . . ?
C27B C23 C26B 106.4(6) . . ?
C23 C24A H24A 110.4 . . ?
C23 C24A H24B 110.4 . . ?
C23 C24A C25 106.4(3) . . ?
H24A C24A H24B 108.6 . . ?
C25 C24A H24A 110.4 . . ?
C25 C24A H24B 110.4 . . ?
C23 C24B H24C 110.5 . . ?
C23 C24B H24D 110.5 . . ?
C23 C24B C25 106.2(5) . . ?
H24C C24B H24D 108.7 . . ?
C25 C24B H24C 110.5 . . ?
C25 C24B H24D 110.5 . . ?
N21 C25 C24A 101.4(2) . . ?
N21 C25 C24B 99.3(4) . . ?
N21 C25 C28 112.0(2) . . ?
N21 C25 C29 113.7(2) . . ?
C28 C25 C24A 121.7(4) . . ?
C28 C25 C24B 95.5(5) . . ?
C28 C25 C29 106.0(3) . . ?
C29 C25 C24A 102.0(4) . . ?
C29 C25 C24B 128.9(5) . . ?
C23 C26A H26A 109.5 . . ?
C23 C26A H26B 109.5 . . ?
C23 C26A H26C 109.5 . . ?
H26A C26A H26B 109.5 . . ?
H26A C26A H26C 109.5 . . ?
H26B C26A H26C 109.5 . . ?
C23 C26B H26D 109.5 . . ?
C23 C26B H26E 109.5 . . ?
C23 C26B H26F 109.5 . . ?
H26D C26B H26E 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?
C23 C27A H27A 109.5 . . ?
C23 C27A H27B 109.5 . . ?
C23 C27A H27C 109.5 . . ?
H27A C27A H27B 109.5 . . ?
H27A C27A H27C 109.5 . . ?
H27B C27A H27C 109.5 . . ?
C23 C27B H27D 109.5 . . ?
C23 C27B H27E 109.5 . . ?
C23 C27B H27F 109.5 . . ?
H27D C27B H27E 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C29 H29A 109.5 . . ?
C25 C29 H29B 109.5 . . ?
C25 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 N21 121.33(19) . . ?
C31 C30 C35 119.2(2) . . ?
C35 C30 N21 119.44(19) . . ?
C30 C31 C36 122.4(2) . . ?
C32 C31 C30 119.2(2) . . ?
C32 C31 C36 118.3(2) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 C31 121.6(2) . . ?
C33 C32 H32 119.2 . . ?
C32 C33 H33 120.3 . . ?
C32 C33 C34 119.4(2) . . ?
C34 C33 H33 120.3 . . ?
C33 C34 H34 119.4 . . ?
C33 C34 C35 121.2(2) . . ?
C35 C34 H34 119.4 . . ?
C30 C35 C39 122.6(2) . . ?
C34 C35 C30 119.3(2) . . ?
C34 C35 C39 118.0(2) . . ?
C31 C36 H36 108.2 . . ?
C31 C36 C37 108.9(2) . . ?
C31 C36 C38 112.3(2) . . ?
C37 C36 H36 108.2 . . ?
C37 C36 C38 111.1(3) . . ?
C38 C36 H36 108.2 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C35 C39 H39 108.1 . . ?
C35 C39 C40 109.9(2) . . ?
C35 C39 C41 112.5(2) . . ?
C40 C39 H39 108.1 . . ?
C40 C39 C41 110.0(2) . . ?
C41 C39 H39 108.1 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C42 N41 C45 114.39(18) . . ?
C42 N41 C50 121.85(17) . . ?
C50 N41 C45 123.23(17) . . ?
F41A C42 N41 117.3(2) . . ?
F41A C42 H42 107.7 . . ?
F41A C42 C43 111.2(2) . . ?
F41B C42 N41 117.9(3) . . ?
F41B C42 H42A 105.9 . . ?
F41B C42 C43 115.7(3) . . ?
N41 C42 H42 107.7 . . ?
N41 C42 H42A 105.9 . . ?
N41 C42 C43 104.76(18) . . ?
C43 C42 H42 107.7 . . ?
C43 C42 H42A 105.9 . . ?
C42 C43 C46B 94.2(7) . . ?
C42 C43 C47A 107.9(2) . . ?
C44A C43 C42 102.2(2) . . ?
C44A C43 C47A 110.6(3) . . ?
C44B C43 C42 107.6(8) . . ?
C44B C43 C46B 109.8(14) . . ?
C44B C43 C47B 126.4(14) . . ?
C46A C43 C42 115.0(3) . . ?
C46A C43 C44A 113.7(3) . . ?
C46A C43 C47A 107.3(4) . . ?
C47B C43 C42 114.9(9) . . ?
C47B C43 C46B 98.4(16) . . ?
C43 C44A H44A 110.2 . . ?
C43 C44A H44B 110.2 . . ?
H44A C44A H44B 108.5 . . ?
C45 C44A C43 107.4(2) . . ?
C45 C44A H44A 110.2 . . ?
C45 C44A H44B 110.2 . . ?
C43 C44B H44C 109.7 . . ?
C43 C44B H44D 109.7 . . ?
C43 C44B C45 109.7(12) . . ?
H44C C44B H44D 108.2 . . ?
C45 C44B H44C 109.7 . . ?
C45 C44B H44D 109.7 . . ?
N41 C45 C44A 101.84(19) . . ?
N41 C45 C44B 95.8(6) . . ?
N41 C45 C48 113.5(2) . . ?
N41 C45 C49 111.66(19) . . ?
C44A C45 C48 106.7(3) . . ?
C44A C45 C49 116.2(3) . . ?
C48 C45 C44B 132.8(8) . . ?
C48 C45 C49 107.0(2) . . ?
C49 C45 C44B 94.2(8) . . ?
C43 C46A H46A 109.5 . . ?
C43 C46A H46B 109.5 . . ?
C43 C46A H46C 109.5 . . ?
H46A C46A H46B 109.5 . . ?
H46A C46A H46C 109.5 . . ?
H46B C46A H46C 109.5 . . ?
C43 C46B H46D 109.5 . . ?
C43 C46B H46E 109.5 . . ?
C43 C46B H46F 109.5 . . ?
H46D C46B H46E 109.5 . . ?
H46D C46B H46F 109.5 . . ?
H46E C46B H46F 109.5 . . ?
C43 C47A H47A 109.5 . . ?
C43 C47A H47B 109.5 . . ?
C43 C47A H47C 109.5 . . ?
H47A C47A H47B 109.5 . . ?
H47A C47A H47C 109.5 . . ?
H47B C47A H47C 109.5 . . ?
C43 C47B H47D 109.5 . . ?
C43 C47B H47E 109.5 . . ?
C43 C47B H47F 109.5 . . ?
H47D C47B H47E 109.5 . . ?
H47D C47B H47F 109.5 . . ?
H47E C47B H47F 109.5 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C45 C49 H49A 109.5 . . ?
C45 C49 H49B 109.5 . . ?
C45 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C51 C50 N41 121.56(18) . . ?
C51 C50 C55 119.03(19) . . ?
C55 C50 N41 119.41(19) . . ?
C50 C51 C56 123.3(2) . . ?
C52 C51 C50 119.4(2) . . ?
C52 C51 C56 117.2(2) . . ?
C51 C52 H52 119.3 . . ?
C53 C52 C51 121.5(2) . . ?
C53 C52 H52 119.3 . . ?
C52 C53 H53 120.5 . . ?
C54 C53 C52 119.0(2) . . ?
C54 C53 H53 120.5 . . ?
C53 C54 H54 119.0 . . ?
C53 C54 C55 122.0(2) . . ?
C55 C54 H54 119.0 . . ?
C50 C55 C59 122.41(19) . . ?
C54 C55 C50 118.9(2) . . ?
C54 C55 C59 118.61(19) . . ?
C51 C56 H56 108.1 . . ?
C51 C56 C58 112.5(2) . . ?
C57 C56 C51 110.01(19) . . ?
C57 C56 H56 108.1 . . ?
C57 C56 C58 109.9(2) . . ?
C58 C56 H56 108.1 . . ?
C56 C57 H57A 109.5 . . ?
C56 C57 H57B 109.5 . . ?
C56 C57 H57C 109.5 . . ?
H57A C57 H57B 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C56 C58 H58A 109.5 . . ?
C56 C58 H58B 109.5 . . ?
C56 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C55 C59 H59 108.0 . . ?
C55 C59 C60 110.43(19) . . ?
C55 C59 C61 112.3(2) . . ?
C60 C59 H59 108.0 . . ?
C60 C59 C61 109.99(19) . . ?
C61 C59 H59 108.0 . . ?
C59 C60 H60A 109.5 . . ?
C59 C60 H60B 109.5 . . ?
C59 C60 H60C 109.5 . . ?
H60A C60 H60B 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C59 C61 H61A 109.5 . . ?
C59 C61 H61B 109.5 . . ?
C59 C61 H61C 109.5 . . ?
H61A C61 H61B 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C2 N1 C5 112.59(17) . . ?
C2 N1 C10 123.67(17) . . ?
C10 N1 C5 123.74(16) . . ?
N1 C2 H2 122.8 . . ?
N1 C2 C3 114.44(19) . . ?
C3 C2 H2 122.8 . . ?
C2 C3 C4 101.26(18) . . ?
C2 C3 C6 110.33(19) . . ?
C2 C3 C7 109.0(2) . . ?
C6 C3 C4 113.6(2) . . ?
C6 C3 C7 109.4(2) . . ?
C7 C3 C4 113.0(2) . . ?
C3 C4 H4A 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
C5 C4 C3 107.50(18) . . ?
C5 C4 H4A 110.2 . . ?
C5 C4 H4B 110.2 . . ?
C4 C5 N1 99.68(17) . . ?
C8 C5 N1 111.70(18) . . ?
C8 C5 C4 112.3(2) . . ?
C8 C5 C9 109.3(2) . . ?
C9 C5 N1 108.05(17) . . ?
C9 C5 C4 115.4(2) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N1 119.15(18) . . ?
C15 C10 N1 117.22(18) . . ?
C15 C10 C11 123.61(18) . . ?
C10 C11 C12 116.0(2) . . ?
C10 C11 C16 124.78(19) . . ?
C12 C11 C16 118.95(19) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.8(2) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.3(2) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C15 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C10 C15 C14 117.15(19) . . ?
C10 C15 C19 123.74(19) . . ?
C14 C15 C19 118.8(2) . . ?
C11 C16 H16 108.0 . . ?
C11 C16 C17 109.95(18) . . ?
C11 C16 C18 112.5(2) . . ?
C17 C16 H16 108.0 . . ?
C17 C16 C18 110.2(2) . . ?
C18 C16 H16 108.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19 107.9 . . ?
C15 C19 C20 113.3(2) . . ?
C15 C19 C21 109.44(19) . . ?
C20 C19 H19 107.9 . . ?
C20 C19 C21 110.3(2) . . ?
C21 C19 H19 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F21A C22 1.361(3) . ?
F21B C22 1.329(8) . ?
N21 C22 1.419(3) . ?
N21 C25 1.482(3) . ?
N21 C30 1.434(3) . ?
C22 H22 1.0000 . ?
C22 H22A 1.0000 . ?
C22 C23 1.535(4) . ?
C23 C24A 1.524(5) . ?
C23 C24B 1.502(9) . ?
C23 C26A 1.528(6) . ?
C23 C26B 1.597(10) . ?
C23 C27A 1.556(6) . ?
C23 C27B 1.503(10) . ?
C24A H24A 0.9900 . ?
C24A H24B 0.9900 . ?
C24A C25 1.559(5) . ?
C24B H24C 0.9900 . ?
C24B H24D 0.9900 . ?
C24B C25 1.584(8) . ?
C25 C28 1.515(4) . ?
C25 C29 1.529(4) . ?
C26A H26A 0.9800 . ?
C26A H26B 0.9800 . ?
C26A H26C 0.9800 . ?
C26B H26D 0.9800 . ?
C26B H26E 0.9800 . ?
C26B H26F 0.9800 . ?
C27A H27A 0.9800 . ?
C27A H27B 0.9800 . ?
C27A H27C 0.9800 . ?
C27B H27D 0.9800 . ?
C27B H27E 0.9800 . ?
C27B H27F 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.407(3) . ?
C30 C35 1.415(3) . ?
C31 C32 1.394(3) . ?
C31 C36 1.521(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.375(4) . ?
C33 H33 0.9500 . ?
C33 C34 1.381(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.394(3) . ?
C35 C39 1.521(3) . ?
C36 H36 1.0000 . ?
C36 C37 1.528(5) . ?
C36 C38 1.541(4) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39 1.0000 . ?
C39 C40 1.528(4) . ?
C39 C41 1.530(4) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
F41A C42 1.369(4) . ?
F41B C42 1.295(5) . ?
N41 C42 1.420(3) . ?
N41 C45 1.487(3) . ?
N41 C50 1.432(3) . ?
C42 H42 1.0000 . ?
C42 H42A 1.0000 . ?
C42 C43 1.543(3) . ?
C43 C44A 1.534(5) . ?
C43 C44B 1.372(17) . ?
C43 C46A 1.499(5) . ?
C43 C46B 1.804(17) . ?
C43 C47A 1.572(6) . ?
C43 C47B 1.43(2) . ?
C44A H44A 0.9900 . ?
C44A H44B 0.9900 . ?
C44A C45 1.526(4) . ?
C44B H44C 0.9900 . ?
C44B H44D 0.9900 . ?
C44B C45 1.64(2) . ?
C45 C48 1.529(4) . ?
C45 C49 1.533(3) . ?
C46A H46A 0.9800 . ?
C46A H46B 0.9800 . ?
C46A H46C 0.9800 . ?
C46B H46D 0.9800 . ?
C46B H46E 0.9800 . ?
C46B H46F 0.9800 . ?
C47A H47A 0.9800 . ?
C47A H47B 0.9800 . ?
C47A H47C 0.9800 . ?
C47B H47D 0.9800 . ?
C47B H47E 0.9800 . ?
C47B H47F 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 C51 1.406(3) . ?
C50 C55 1.421(3) . ?
C51 C52 1.398(3) . ?
C51 C56 1.528(3) . ?
C52 H52 0.9500 . ?
C52 C53 1.383(3) . ?
C53 H53 0.9500 . ?
C53 C54 1.372(3) . ?
C54 H54 0.9500 . ?
C54 C55 1.397(3) . ?
C55 C59 1.520(3) . ?
C56 H56 1.0000 . ?
C56 C57 1.524(4) . ?
C56 C58 1.532(4) . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C59 H59 1.0000 . ?
C59 C60 1.528(3) . ?
C59 C61 1.538(3) . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
N1 C2 1.275(3) . ?
N1 C5 1.545(3) . ?
N1 C10 1.464(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.486(3) . ?
C3 C4 1.546(3) . ?
C3 C6 1.525(4) . ?
C3 C7 1.542(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.536(3) . ?
C5 C8 1.520(3) . ?
C5 C9 1.521(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.399(3) . ?
C10 C15 1.393(3) . ?
C11 C12 1.408(3) . ?
C11 C16 1.511(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.368(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.398(3) . ?
C15 C19 1.524(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.536(3) . ?
C16 C18 1.537(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19 1.0000 . ?
C19 C20 1.525(4) . ?
C19 C21 1.529(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
F1 H1 1.18(4) . ?
F2 H1 1.06(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F21A C22 C23 C24A 157.4(4) . . . . ?
F21A C22 C23 C26A -79.2(4) . . . . ?
F21A C22 C23 C27A 41.2(4) . . . . ?
F21B C22 C23 C24B -139.7(7) . . . . ?
F21B C22 C23 C26B -26.0(7) . . . . ?
F21B C22 C23 C27B 87.6(7) . . . . ?
N21 C22 C23 C24A 26.2(4) . . . . ?
N21 C22 C23 C24B -7.0(6) . . . . ?
N21 C22 C23 C26A 149.6(4) . . . . ?
N21 C22 C23 C26B 106.8(5) . . . . ?
N21 C22 C23 C27A -90.0(4) . . . . ?
N21 C22 C23 C27B -139.6(5) . . . . ?
N21 C30 C31 C32 178.8(2) . . . . ?
N21 C30 C31 C36 -5.0(3) . . . . ?
N21 C30 C35 C34 -178.6(2) . . . . ?
N21 C30 C35 C39 5.7(3) . . . . ?
C22 N21 C25 C24A -5.8(4) . . . . ?
C22 N21 C25 C24B 25.5(6) . . . . ?
C22 N21 C25 C28 125.4(3) . . . . ?
C22 N21 C25 C29 -114.5(3) . . . . ?
C22 N21 C30 C31 78.1(3) . . . . ?
C22 N21 C30 C35 -99.9(3) . . . . ?
C22 C23 C24A C25 -30.1(5) . . . . ?
C22 C23 C24B C25 22.3(9) . . . . ?
C23 C24A C25 N21 22.4(5) . . . . ?
C23 C24A C25 C28 -102.5(4) . . . . ?
C23 C24A C25 C29 140.0(4) . . . . ?
C23 C24B C25 N21 -28.0(8) . . . . ?
C23 C24B C25 C28 -141.5(7) . . . . ?
C23 C24B C25 C29 102.9(7) . . . . ?
C25 N21 C22 F21A -143.4(3) . . . . ?
C25 N21 C22 F21B 118.1(5) . . . . ?
C25 N21 C22 C23 -12.9(3) . . . . ?
C25 N21 C30 C31 -88.2(3) . . . . ?
C25 N21 C30 C35 93.8(3) . . . . ?
C26A C23 C24A C25 -154.5(5) . . . . ?
C26B C23 C24B C25 -83.1(8) . . . . ?
C27A C23 C24A C25 83.0(5) . . . . ?
C27B C23 C24B C25 155.9(6) . . . . ?
C30 N21 C22 F21A 49.2(4) . . . . ?
C30 N21 C22 F21B -49.4(5) . . . . ?
C30 N21 C22 C23 179.7(2) . . . . ?
C30 N21 C25 C24A 161.3(4) . . . . ?
C30 N21 C25 C24B -167.3(5) . . . . ?
C30 N21 C25 C28 -67.5(3) . . . . ?
C30 N21 C25 C29 52.7(3) . . . . ?
C30 C31 C32 C33 1.1(4) . . . . ?
C30 C31 C36 C37 -106.1(3) . . . . ?
C30 C31 C36 C38 130.5(3) . . . . ?
C30 C35 C39 C40 109.2(2) . . . . ?
C30 C35 C39 C41 -127.8(2) . . . . ?
C31 C30 C35 C34 3.4(3) . . . . ?
C31 C30 C35 C39 -172.4(2) . . . . ?
C31 C32 C33 C34 0.7(4) . . . . ?
C32 C31 C36 C37 70.1(3) . . . . ?
C32 C31 C36 C38 -53.3(3) . . . . ?
C32 C33 C34 C35 -0.5(4) . . . . ?
C33 C34 C35 C30 -1.5(4) . . . . ?
C33 C34 C35 C39 174.4(2) . . . . ?
C34 C35 C39 C40 -66.6(3) . . . . ?
C34 C35 C39 C41 56.4(3) . . . . ?
C35 C30 C31 C32 -3.2(3) . . . . ?
C35 C30 C31 C36 173.0(2) . . . . ?
C36 C31 C32 C33 -175.2(3) . . . . ?
F41A C42 C43 C44A 99.6(3) . . . . ?
F41A C42 C43 C46A -24.1(5) . . . . ?
F41A C42 C43 C47A -143.7(3) . . . . ?
F41B C42 C43 C44B -128.7(12) . . . . ?
F41B C42 C43 C46B 119.0(10) . . . . ?
F41B C42 C43 C47B 17.7(14) . . . . ?
N41 C42 C43 C44A -28.0(3) . . . . ?
N41 C42 C43 C44B 2.8(12) . . . . ?
N41 C42 C43 C46A -151.8(4) . . . . ?
N41 C42 C43 C46B -109.5(10) . . . . ?
N41 C42 C43 C47A 88.6(3) . . . . ?
N41 C42 C43 C47B 149.3(13) . . . . ?
N41 C50 C51 C52 -177.58(18) . . . . ?
N41 C50 C51 C56 5.5(3) . . . . ?
N41 C50 C55 C54 177.04(18) . . . . ?
N41 C50 C55 C59 -6.6(3) . . . . ?
C42 N41 C45 C44A 2.1(3) . . . . ?
C42 N41 C45 C44B -25.7(9) . . . . ?
C42 N41 C45 C48 116.4(3) . . . . ?
C42 N41 C45 C49 -122.5(2) . . . . ?
C42 N41 C50 C51 -84.1(3) . . . . ?
C42 N41 C50 C55 94.6(2) . . . . ?
C42 C43 C44A C45 30.3(3) . . . . ?
C42 C43 C44B C45 -19.1(16) . . . . ?
C43 C44A C45 N41 -20.5(3) . . . . ?
C43 C44A C45 C48 -139.8(3) . . . . ?
C43 C44A C45 C49 101.0(3) . . . . ?
C43 C44B C45 N41 26.8(15) . . . . ?
C43 C44B C45 C48 -103.1(13) . . . . ?
C43 C44B C45 C49 139.1(13) . . . . ?
C45 N41 C42 F41A -107.1(3) . . . . ?
C45 N41 C42 F41B 147.1(4) . . . . ?
C45 N41 C42 C43 16.8(3) . . . . ?
C45 N41 C50 C51 87.0(3) . . . . ?
C45 N41 C50 C55 -94.2(2) . . . . ?
C46A C43 C44A C45 154.8(3) . . . . ?
C46B C43 C44B C45 82.2(15) . . . . ?
C47A C43 C44A C45 -84.4(3) . . . . ?
C47B C43 C44B C45 -160.6(16) . . . . ?
C50 N41 C42 F41A 64.8(3) . . . . ?
C50 N41 C42 F41B -41.0(4) . . . . ?
C50 N41 C42 C43 -171.3(2) . . . . ?
C50 N41 C45 C44A -169.7(3) . . . . ?
C50 N41 C45 C44B 162.6(9) . . . . ?
C50 N41 C45 C48 -55.3(3) . . . . ?
C50 N41 C45 C49 65.7(3) . . . . ?
C50 C51 C52 C53 -0.6(3) . . . . ?
C50 C51 C56 C57 110.1(2) . . . . ?
C50 C51 C56 C58 -127.1(2) . . . . ?
C50 C55 C59 C60 -108.4(2) . . . . ?
C50 C55 C59 C61 128.4(2) . . . . ?
C51 C50 C55 C54 -4.2(3) . . . . ?
C51 C50 C55 C59 172.22(18) . . . . ?
C51 C52 C53 C54 -1.9(3) . . . . ?
C52 C51 C56 C57 -67.0(3) . . . . ?
C52 C51 C56 C58 55.9(3) . . . . ?
C52 C53 C54 C55 1.3(3) . . . . ?
C53 C54 C55 C50 1.7(3) . . . . ?
C53 C54 C55 C59 -174.8(2) . . . . ?
C54 C55 C59 C60 67.9(3) . . . . ?
C54 C55 C59 C61 -55.2(3) . . . . ?
C55 C50 C51 C52 3.6(3) . . . . ?
C55 C50 C51 C56 -173.31(18) . . . . ?
C56 C51 C52 C53 176.5(2) . . . . ?
N1 C2 C3 C4 -10.1(2) . . . . ?
N1 C2 C3 C6 110.4(2) . . . . ?
N1 C2 C3 C7 -129.5(2) . . . . ?
N1 C10 C11 C12 177.63(17) . . . . ?
N1 C10 C11 C16 -7.9(3) . . . . ?
N1 C10 C15 C14 -177.50(18) . . . . ?
N1 C10 C15 C19 8.7(3) . . . . ?
C2 N1 C5 C4 15.3(2) . . . . ?
C2 N1 C5 C8 134.2(2) . . . . ?
C2 N1 C5 C9 -105.6(2) . . . . ?
C2 N1 C10 C11 85.5(2) . . . . ?
C2 N1 C10 C15 -92.7(2) . . . . ?
C2 C3 C4 C5 19.4(2) . . . . ?
C3 C4 C5 N1 -20.7(2) . . . . ?
C3 C4 C5 C8 -139.1(2) . . . . ?
C3 C4 C5 C9 94.8(2) . . . . ?
C5 N1 C2 C3 -3.4(3) . . . . ?
C5 N1 C10 C11 -93.9(2) . . . . ?
C5 N1 C10 C15 87.9(2) . . . . ?
C6 C3 C4 C5 -98.9(2) . . . . ?
C7 C3 C4 C5 135.9(2) . . . . ?
C10 N1 C2 C3 177.14(18) . . . . ?
C10 N1 C5 C4 -165.24(19) . . . . ?
C10 N1 C5 C8 -46.4(3) . . . . ?
C10 N1 C5 C9 73.8(2) . . . . ?
C10 C11 C12 C13 1.5(3) . . . . ?
C10 C11 C16 C17 -110.6(2) . . . . ?
C10 C11 C16 C18 126.1(2) . . . . ?
C10 C15 C19 C20 -133.7(2) . . . . ?
C10 C15 C19 C21 102.8(3) . . . . ?
C11 C10 C15 C14 4.4(3) . . . . ?
C11 C10 C15 C19 -169.38(19) . . . . ?
C11 C12 C13 C14 1.1(3) . . . . ?
C12 C11 C16 C17 63.7(3) . . . . ?
C12 C11 C16 C18 -59.5(3) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 C14 C15 C10 -1.6(3) . . . . ?
C13 C14 C15 C19 172.50(19) . . . . ?
C14 C15 C19 C20 52.6(3) . . . . ?
C14 C15 C19 C21 -70.9(3) . . . . ?
C15 C10 C11 C12 -4.3(3) . . . . ?
C15 C10 C11 C16 170.17(19) . . . . ?
C16 C11 C12 C13 -173.37(19) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7935(10)
2 0.2065(10)
