#------------------------------------------------------------------------------
#$Date: 2023-06-29 13:50:08 +0300 (Thu, 29 Jun 2023) $
#$Revision: 284613 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/32/7713263.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_7713263
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         'C20 H32 N, F3 H2'
_chemical_formula_sum            'C20 H34 F3 N'
_chemical_formula_weight         345.48
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-17
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-05-16 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.161(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8109(4)
_cell_length_b                   9.4778(3)
_cell_length_c                   20.4419(7)
_cell_measurement_reflns_used    4945
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      71.7950
_cell_measurement_theta_min      4.2480
_cell_volume                     2039.53(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6426
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00  35.00   1.00    2.46    --  -41.11  77.00 -20.00  108
  2  ω    -21.00  50.00   1.00    2.46    --   41.11 -77.00-146.00   71
  3  ω     51.00  82.00   1.00    9.84    --  103.58 -77.00-146.00   31
  4  ω    110.00 178.00   1.00    9.84    --  103.58  77.00 -20.00   68
  5  ω    -73.00  28.00   1.00    2.46    --  -41.11  77.00 120.00  101
  6  ω     38.00 112.00   1.00    2.46    --   41.11  57.00  90.00   74
  7  ω     20.00  63.00   1.00    2.46    --   41.11  57.00  60.00   43
  8  ω     57.00 109.00   1.00    2.46    --   41.11  57.00   0.00   52
  9  ω    103.00 178.00   1.00    9.84    --  103.58  77.00  60.00   75
 10  ω     26.00 116.00   1.00    9.84    --  103.58 -80.00 165.57   90
 11  ω     99.00 176.00   1.00    9.84    --  103.58  45.00  30.00   77
 12  ω     76.00 103.00   1.00    9.84    --  103.58 -79.00 131.21   27
 13  ω     64.00 115.00   1.00    9.84    --  103.58 -80.00-106.30   51
 14  ω     35.00  60.00   1.00    9.84    --  103.58 -80.00-106.30   25
 15  ω     86.00 173.00   1.00    9.84    --  103.58  45.00 120.00   87
 16  ω     76.00 103.00   1.00    9.84    --  103.58 -80.00  91.02   27
 17  ω     30.00  55.00   1.00    9.84    --  103.58 -79.00 -32.50   25
 18  ω     88.00 124.00   1.00    9.84    --  103.58 -79.00 -32.50   36
 19  ω     32.00  67.00   1.00    9.84    --  103.58 -45.00  30.00   35
 20  ω    104.00 150.00   1.00    9.84    --  103.58  77.00 150.00   46
 21  ω     81.00 108.00   1.00    9.84    --  103.58 -45.00  30.00   27
 22  ω     58.00  85.00   1.00    9.84    --  103.58 -79.00  47.66   27
 23  ω    118.00 168.00   1.00    9.84    --  103.58  45.00 -60.00   50
 24  ω     27.00 124.00   1.00    9.84    --  103.58 -80.00   5.22   97
 25  ω     41.00  66.00   1.00    9.84    --  103.58 -45.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1431681000
_diffrn_orient_matrix_UB_12      0.0251236000
_diffrn_orient_matrix_UB_13      -0.0069948000
_diffrn_orient_matrix_UB_21      0.0050320000
_diffrn_orient_matrix_UB_22      -0.0856080000
_diffrn_orient_matrix_UB_23      0.0646251000
_diffrn_orient_matrix_UB_31      0.0297611000
_diffrn_orient_matrix_UB_32      0.1359131000
_diffrn_orient_matrix_UB_33      0.0420024000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16584
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         72.274
_diffrn_reflns_theta_min         4.281
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.125
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.459
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.197
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0650P)²+0.6968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1391
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3211
_reflns_number_total             3973
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt01476b2.cif
_cod_data_source_block           exp_698_573_mecaach+h2f3-
_cod_original_cell_volume        2039.53(12)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7713263
_shelxl_version_number           2017/1
_chemical_oxdiff_formula         'C20 H32 N F3'
_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.
;
_shelx_estimated_absorpt_t_max   0.877
_shelx_estimated_absorpt_t_min   0.744
_olex2_refinement_description
;
1. 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
2. Others
 Fixed Uiso: H2B(0.05135)
3.a Ternary CH refined with riding coordinates:
 C16(H16), C19(H19)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C12(H12), C13(H13), C14(H14)
3.d Idealised Me refined as rotating group:
 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(H21B,H21A,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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.227
_oxdiff_exptl_absorpt_empirical_full_min 0.840
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
N1 N 0.53038(12) 0.19539(13) 0.34687(6) 0.0268(3) Uani 1 1 d . . . . .
C2 C 0.51463(14) 0.28118(17) 0.29761(7) 0.0301(3) Uani 1 1 d . . . . .
H2 H 0.498733 0.378911 0.301963 0.036 Uiso 1 1 calc R U . . .
C3 C 0.52329(16) 0.21508(18) 0.23255(7) 0.0332(4) Uani 1 1 d . . . . .
C4 C 0.57555(17) 0.06739(18) 0.25575(8) 0.0367(4) Uani 1 1 d . . . . .
H4A H 0.667642 0.062728 0.257277 0.044 Uiso 1 1 calc R U . . .
H4B H 0.531776 -0.005525 0.224129 0.044 Uiso 1 1 calc R U . . .
C5 C 0.55155(16) 0.04191(17) 0.32664(8) 0.0318(3) Uani 1 1 d . . . . .
C6 C 0.61403(19) 0.3008(2) 0.20015(9) 0.0457(4) Uani 1 1 d . . . . .
H6A H 0.577868 0.394494 0.187869 0.069 Uiso 1 1 calc R U . . .
H6B H 0.625961 0.251962 0.159774 0.069 Uiso 1 1 calc R U . . .
H6C H 0.696179 0.310527 0.232135 0.069 Uiso 1 1 calc R U . . .
C7 C 0.39054(19) 0.2143(2) 0.18545(9) 0.0477(5) Uani 1 1 d . . . . .
H7A H 0.332242 0.160130 0.206097 0.072 Uiso 1 1 calc R U . . .
H7B H 0.395050 0.170902 0.142543 0.072 Uiso 1 1 calc R U . . .
H7C H 0.359608 0.311446 0.177640 0.072 Uiso 1 1 calc R U . . .
C8 C 0.66508(18) -0.0218(2) 0.37544(9) 0.0407(4) Uani 1 1 d . . . . .
H8A H 0.741964 0.030936 0.373173 0.061 Uiso 1 1 calc R U . . .
H8B H 0.674976 -0.120597 0.363448 0.061 Uiso 1 1 calc R U . . .
H8C H 0.651520 -0.016815 0.421184 0.061 Uiso 1 1 calc R U . . .
C9 C 0.43323(18) -0.04533(18) 0.32592(9) 0.0406(4) Uani 1 1 d . . . . .
H9A H 0.417655 -0.048588 0.371285 0.061 Uiso 1 1 calc R U . . .
H9B H 0.445623 -0.141387 0.310855 0.061 Uiso 1 1 calc R U . . .
H9C H 0.360134 -0.002252 0.295150 0.061 Uiso 1 1 calc R U . . .
C10 C 0.53133(14) 0.24139(16) 0.41527(7) 0.0275(3) Uani 1 1 d . . . . .
C11 C 0.41747(15) 0.24126(16) 0.43713(7) 0.0296(3) Uani 1 1 d . . . . .
C12 C 0.42438(16) 0.28514(18) 0.50316(8) 0.0342(4) Uani 1 1 d . . . . .
H12 H 0.349417 0.285438 0.520004 0.041 Uiso 1 1 calc R U . . .
C13 C 0.53768(17) 0.32806(18) 0.54448(8) 0.0369(4) Uani 1 1 d . . . . .
H13 H 0.540397 0.355281 0.589513 0.044 Uiso 1 1 calc R U . . .
C14 C 0.64718(16) 0.33139(18) 0.52029(8) 0.0357(4) Uani 1 1 d . . . . .
H14 H 0.724119 0.363343 0.548795 0.043 Uiso 1 1 calc R U . . .
C15 C 0.64710(15) 0.28887(17) 0.45495(8) 0.0308(3) Uani 1 1 d . . . . .
C16 C 0.28812(15) 0.20767(18) 0.39198(8) 0.0334(4) Uani 1 1 d . . . . .
H16 H 0.302274 0.169554 0.348653 0.040 Uiso 1 1 calc R U . . .
C17 C 0.21559(17) 0.0962(2) 0.42252(10) 0.0435(4) Uani 1 1 d . . . . .
H17A H 0.268357 0.011598 0.433577 0.065 Uiso 1 1 calc R U . . .
H17B H 0.136873 0.071785 0.390076 0.065 Uiso 1 1 calc R U . . .
H17C H 0.195108 0.133780 0.463446 0.065 Uiso 1 1 calc R U . . .
C18 C 0.20859(17) 0.3428(2) 0.37628(10) 0.0433(4) Uani 1 1 d . . . . .
H18A H 0.194467 0.383040 0.418137 0.065 Uiso 1 1 calc R U . . .
H18B H 0.126600 0.320331 0.346231 0.065 Uiso 1 1 calc R U . . .
H18C H 0.253933 0.411288 0.354449 0.065 Uiso 1 1 calc R U . . .
C19 C 0.76776(16) 0.3048(2) 0.42874(8) 0.0369(4) Uani 1 1 d . . . . .
H19 H 0.753855 0.254418 0.384689 0.044 Uiso 1 1 calc R U . . .
C20 C 0.79267(19) 0.4601(2) 0.41610(10) 0.0490(5) Uani 1 1 d . . . . .
H20A H 0.718914 0.499835 0.384499 0.074 Uiso 1 1 calc R U . . .
H20B H 0.867825 0.467865 0.397088 0.074 Uiso 1 1 calc R U . . .
H20C H 0.807235 0.512106 0.458599 0.074 Uiso 1 1 calc R U . . .
C21 C 0.88389(17) 0.2385(3) 0.47585(10) 0.0525(5) Uani 1 1 d . . . . .
H21B H 0.956359 0.241124 0.454506 0.079 Uiso 1 1 calc R U . . .
H21A H 0.864959 0.140298 0.485070 0.079 Uiso 1 1 calc R U . . .
H21C H 0.904617 0.291497 0.518085 0.079 Uiso 1 1 calc R U . . .
F1 F 0.35431(15) 0.56385(16) 0.26863(9) 0.0757(4) Uani 1 1 d . . . . .
H2B H 0.442(2) 0.601(2) 0.2673(11) 0.051 Uiso 1 1 d . U . . .
F2 F 0.55941(13) 0.63517(16) 0.29007(7) 0.0655(4) Uani 1 1 d . . . . .
H2A H 0.570(3) 0.675(4) 0.2290(18) 0.101(11) Uiso 1 1 d . . . . .
F3 F 0.60850(14) 0.6990(2) 0.18938(8) 0.0823(5) 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 -1 13 0.1046
0 0 -13 0.0965
0 5 -6 0.1677
0 -5 8 0.1852
7 0 -3 0.0958
-7 0 4 0.0972
5 4 2 0.1707
-7 1 5 0.0906
-5 -4 -2 0.1197
4 -4 -8 0.1568
5 0 -11 0.1042
3 5 2 0.1972
5 4 -5 0.1610
-6 -2 9 0.1206
-4 1 -9 0.0906
4 -1 10 0.1176
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
C2 N1 C5 113.00(12) . . ?
C2 N1 C10 122.38(13) . . ?
C10 N1 C5 124.60(12) . . ?
N1 C2 H2 122.8 . . ?
N1 C2 C3 114.32(14) . . ?
C3 C2 H2 122.8 . . ?
C2 C3 C4 101.52(12) . . ?
C2 C3 C6 109.77(14) . . ?
C2 C3 C7 108.76(15) . . ?
C6 C3 C4 112.79(15) . . ?
C6 C3 C7 109.26(14) . . ?
C7 C3 C4 114.40(15) . . ?
C3 C4 H4A 110.2 . . ?
C3 C4 H4B 110.2 . . ?
C3 C4 C5 107.55(13) . . ?
H4A C4 H4B 108.5 . . ?
C5 C4 H4A 110.2 . . ?
C5 C4 H4B 110.2 . . ?
N1 C5 C4 99.81(12) . . ?
C8 C5 N1 110.21(13) . . ?
C8 C5 C4 113.21(14) . . ?
C8 C5 C9 110.02(14) . . ?
C9 C5 N1 109.84(13) . . ?
C9 C5 C4 113.31(14) . . ?
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 119.27(13) . . ?
C15 C10 N1 117.38(13) . . ?
C15 C10 C11 123.30(14) . . ?
C10 C11 C16 123.96(14) . . ?
C12 C11 C10 116.72(14) . . ?
C12 C11 C16 119.14(14) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.54(15) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.00(15) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.45(15) . . ?
C15 C14 H14 119.3 . . ?
C10 C15 C19 123.41(14) . . ?
C14 C15 C10 116.91(15) . . ?
C14 C15 C19 119.55(15) . . ?
C11 C16 H16 107.9 . . ?
C11 C16 C17 112.45(14) . . ?
C11 C16 C18 110.21(14) . . ?
C17 C16 H16 107.9 . . ?
C17 C16 C18 110.28(15) . . ?
C18 C16 H16 107.9 . . ?
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 107.7 . . ?
C15 C19 C20 110.62(15) . . ?
C15 C19 C21 112.48(14) . . ?
C20 C19 H19 107.7 . . ?
C20 C19 C21 110.53(16) . . ?
C21 C19 H19 107.7 . . ?
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 H21B 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21B C21 H21A 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H2B F2 H2A 91.3(17) . . ?
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
N1 C2 1.275(2) . ?
N1 C5 1.543(2) . ?
N1 C10 1.4626(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.492(2) . ?
C3 C4 1.543(2) . ?
C3 C6 1.535(2) . ?
C3 C7 1.535(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.548(2) . ?
C5 C8 1.519(2) . ?
C5 C9 1.520(2) . ?
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 1.402(2) . ?
C10 C15 1.402(2) . ?
C11 C12 1.398(2) . ?
C11 C16 1.523(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.395(2) . ?
C15 C19 1.526(2) . ?
C16 H16 1.0000 . ?
C16 C17 1.531(2) . ?
C16 C18 1.535(2) . ?
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 1.529(3) . ?
C19 C21 1.532(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21C 0.9800 . ?
F1 H2B 1.02(2) . ?
F2 H2B 1.29(2) . ?
F2 H2A 1.33(4) . ?
F3 H2A 1.01(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
N1 C2 C3 C4 -10.79(18) . . . . ?
N1 C2 C3 C6 -130.34(16) . . . . ?
N1 C2 C3 C7 110.17(16) . . . . ?
N1 C10 C11 C12 179.46(14) . . . . ?
N1 C10 C11 C16 -5.5(2) . . . . ?
N1 C10 C15 C14 -179.48(14) . . . . ?
N1 C10 C15 C19 4.7(2) . . . . ?
C2 N1 C5 C4 12.81(17) . . . . ?
C2 N1 C5 C8 132.13(15) . . . . ?
C2 N1 C5 C9 -106.48(15) . . . . ?
C2 N1 C10 C11 91.66(18) . . . . ?
C2 N1 C10 C15 -85.95(18) . . . . ?
C2 C3 C4 C5 18.32(16) . . . . ?
C3 C4 C5 N1 -18.66(16) . . . . ?
C3 C4 C5 C8 -135.77(15) . . . . ?
C3 C4 C5 C9 98.05(16) . . . . ?
C5 N1 C2 C3 -1.41(19) . . . . ?
C5 N1 C10 C11 -90.11(18) . . . . ?
C5 N1 C10 C15 92.29(18) . . . . ?
C6 C3 C4 C5 135.72(15) . . . . ?
C7 C3 C4 C5 -98.59(17) . . . . ?
C10 N1 C2 C3 177.02(13) . . . . ?
C10 N1 C5 C4 -165.57(13) . . . . ?
C10 N1 C5 C8 -46.25(19) . . . . ?
C10 N1 C5 C9 75.14(18) . . . . ?
C10 C11 C12 C13 0.8(2) . . . . ?
C10 C11 C16 C17 129.30(17) . . . . ?
C10 C11 C16 C18 -107.21(18) . . . . ?
C10 C15 C19 C20 103.76(18) . . . . ?
C10 C15 C19 C21 -132.11(18) . . . . ?
C11 C10 C15 C14 3.0(2) . . . . ?
C11 C10 C15 C19 -172.85(15) . . . . ?
C11 C12 C13 C14 1.5(3) . . . . ?
C12 C11 C16 C17 -55.7(2) . . . . ?
C12 C11 C16 C18 67.76(19) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
C13 C14 C15 C10 -0.6(2) . . . . ?
C13 C14 C15 C19 175.42(16) . . . . ?
C14 C15 C19 C20 -72.00(19) . . . . ?
C14 C15 C19 C21 52.1(2) . . . . ?
C15 C10 C11 C12 -3.1(2) . . . . ?
C15 C10 C11 C16 172.00(15) . . . . ?
C16 C11 C12 C13 -174.58(15) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0051 -0.9973 12.9998 -0.1167 0.9255 0.4106
-0.0053 -0.0024 -12.9999 0.0916 -0.8399 -0.5465
-0.0013 4.9978 -5.9996 0.1677 -0.8156 0.4272
0.0021 -4.9974 7.9996 -0.1818 0.9448 -0.3431
7.0001 -0.0000 -3.0070 -0.9812 -0.1591 0.0820
-6.9997 0.0002 4.0070 0.9741 0.2237 -0.0400
5.0027 3.9999 1.9952 -0.6297 -0.1883 0.7763
-6.9990 1.0002 5.0070 0.9921 0.2027 0.1379
-5.0027 -3.9999 -1.9952 0.6297 0.1883 -0.7763
3.9966 -4.0003 -8.0042 -0.6167 -0.1547 -0.7609
4.9964 -0.0017 -11.0049 -0.6384 -0.6859 -0.3138
3.0025 4.9995 1.9973 -0.3182 -0.2838 0.8527
4.9998 3.9986 -5.0047 -0.5803 -0.6406 0.4820
-5.9979 -1.9983 9.0058 0.7455 0.7229 -0.0718
-4.0042 0.9978 -8.9959 0.6613 -0.6869 -0.3614
4.0046 -0.9976 9.9959 -0.6683 0.7515 0.4034
