#------------------------------------------------------------------------------
#$Date: 2023-10-19 00:56:02 +0300 (Thu, 19 Oct 2023) $
#$Revision: 287017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/22/7132221.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_7132221
loop_
_publ_author_name
'Tan, Yongbo'
'Huang, Huawen'
_publ_section_title
;
 Catalyst- and additive-free cascade radical addition/cyclization of
 N-arylacrylamides with trifluoropyruvates
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04542K
_journal_year                    2023
_chemical_formula_moiety         'C21 H20 F3 N O4'
_chemical_formula_sum            'C21 H20 F3 N O4'
_chemical_formula_weight         407.38
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-06-12
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-06-22 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                103.431(2)
_cell_angle_beta                 92.656(2)
_cell_angle_gamma                90.100(2)
_cell_formula_units_Z            4
_cell_length_a                   10.2852(2)
_cell_length_b                   11.2257(3)
_cell_length_c                   17.4566(4)
_cell_measurement_reflns_used    15304
_cell_measurement_temperature    297.44(10)
_cell_measurement_theta_max      77.1190
_cell_measurement_theta_min      4.0340
_cell_volume                     1958.12(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.44(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     96.00 168.00   0.50    0.30    --  108.37  19.00  30.00  144
  2  ω     95.00 166.00   0.50    0.30    --  108.37 125.00  30.00  142
  3  ω    106.00 177.00   0.50    0.30    --  108.37  85.00 -93.00  142
  4  ω    153.00 178.00   0.50    0.30    --  108.37  37.00 -60.00   50
  5  ω     79.00 105.00   0.50    0.30    --  108.37 -85.00 147.00   52
  6  ω     79.00 108.00   0.50    0.30    --  108.37-108.00 110.29   58
  7  ω     70.00 104.00   0.50    0.30    --  108.37-125.00 120.00   68
  8  ω     40.00  69.00   0.50    0.30    --  108.37-108.00 110.29   58
  9  ω     66.00 101.00   0.50    0.30    --  108.37 -99.00  30.00   70
 10  ω     55.00 101.00   0.50    0.30    --  108.37 -99.00   0.00   92
 11  ω     36.00  94.00   0.50    0.30    --  108.37 -99.00 -30.00  116
 12  ω     64.00 111.00   0.50    0.30    --  108.37-125.00 -90.00   94
 13  ω     47.00 108.00   0.50    0.30    --  108.37-125.00-150.00  122
 14  ω     81.00 106.00   0.50    0.30    --  108.37 -99.00-120.00   50
 15  ω     51.00 106.00   0.50    0.30    --  108.37 -99.00 -60.00  110
 16  ω     38.00  63.00   0.50    0.30    --  108.37 -99.00  30.00   50
 17  ω    -21.00  57.00   0.50    0.10    --   48.32 -85.00 147.00  156
 18  ω     81.00 106.00   0.50    0.30    --  108.37 -99.00 150.00   50
 19  ω     40.00  66.00   0.50    0.30    --  108.37 -57.00  90.00   52
 20  ω     40.00  66.00   0.50    0.30    --  108.37 -57.00   0.00   52
 21  ω    -18.00   8.00   0.50    0.10    --   48.32 -19.00-120.00   52
 22  ω     41.00  66.00   0.50    0.30    --  108.37 -57.00 -60.00   50
 23  ω    -28.00  10.00   0.50    0.10    --  -48.32  37.00-150.00   76
 24  ω    -22.00  25.00   0.50    0.10    --  -48.32  19.00-180.00   94
 25  ω    -24.00  17.00   0.50    0.10    --  -48.32  19.00 -90.00   82
 26  ω     -8.00  26.00   0.50    0.10    --  -48.32  19.00 -60.00   68
 27  ω   -103.00 -69.00   0.50    0.30    --  -91.75  77.00-150.00   68
 28  ω    -63.00 -29.00   0.50    0.30    --  -91.75  77.00-150.00   68
 29  ω    -62.00 -19.00   0.50    0.30    --  -91.75  57.00  90.00   86
 30  ω    -66.00 -23.00   0.50    0.30    --  -91.75  57.00 120.00   86
 31  ω    -70.00  23.00   0.50    0.10    --  -48.32  85.00 -93.00  186
 32  ω    -69.00 -36.00   0.50    0.30    --  -91.75  85.00 -93.00   66
 33  ω   -166.00 -81.00   0.50    0.30    --  -91.75 -19.00-150.00  170
 34  ω   -153.00 -79.00   0.50    0.30    --  -91.75 -19.00 -90.00  148
 35  ω   -120.00 -79.00   0.50    0.30    --  -91.75 -19.00 150.00   82
 36  ω   -161.00-136.00   0.50    0.30    --  -91.75 -19.00 150.00   50
 37  ω   -128.00 -92.00   0.50    0.30    --  -91.75 -85.00 147.00   72
 38  ω   -127.00-101.00   0.50    0.30    --  -91.75 -99.00  90.00   52
 39  ω   -154.00-128.00   0.50    0.30    --  -91.75 -99.00  90.00   52
 40  ω   -119.00 -73.00   0.50    0.10    --  -48.32-125.00 -90.00   92
 41  ω   -120.00 -93.00   0.50    0.10    --  -48.32-125.00-150.00   54
 42  ω   -139.00 -88.00   0.50    0.30    --  -91.75 -99.00-150.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0883812000
_diffrn_orient_matrix_UB_12      -0.0631791000
_diffrn_orient_matrix_UB_13      -0.0716306000
_diffrn_orient_matrix_UB_21      0.0167680000
_diffrn_orient_matrix_UB_22      0.1111018000
_diffrn_orient_matrix_UB_23      -0.0366076000
_diffrn_orient_matrix_UB_31      0.1199789000
_diffrn_orient_matrix_UB_32      -0.0597961000
_diffrn_orient_matrix_UB_33      -0.0421940000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24458
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.639
_diffrn_reflns_theta_min         2.605
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.977
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     530
_refine_ls_number_reflns         7798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0419
_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)+(0.0643P)²+0.1595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1242
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6413
_reflns_number_total             7798
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04542k2.cif
_cod_data_source_block           1-dr1
_cod_database_code               7132221
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O F'
_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   0.917
_shelx_estimated_absorpt_t_min   0.844
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C15(H15A,H15B), C22(H22A,H22B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C32(H32), C33(H33), C34(H34), C35(H35), C38(H38), C39(H39), C40(H40),
  C41(H41), C42(H42)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C14(H14A,H14B,H14C), C23(H23A,H23B,H23C), C29(H29A,H29B,H29C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O8(H8)
;
_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 1.531
_oxdiff_exptl_absorpt_empirical_full_min 0.365
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
F1 F 0.06231(11) 0.16358(11) 0.33996(6) 0.0734(3) Uani 1 1 d . . . . .
F2 F -0.08923(11) 0.28426(12) 0.38760(7) 0.0837(4) Uani 1 1 d . . . . .
F3 F -0.07813(12) 0.10399(12) 0.40906(7) 0.0811(3) Uani 1 1 d . . . . .
O1 O 0.15637(10) 0.34617(10) 0.46253(7) 0.0516(3) Uani 1 1 d . . . . .
H1 H 0.113816 0.409073 0.468372 0.077 Uiso 1 1 calc R U . . .
O2 O -0.02062(15) 0.41739(11) 0.56671(8) 0.0741(4) Uani 1 1 d . . . . .
O3 O -0.07532(10) 0.22580(10) 0.57102(7) 0.0534(3) Uani 1 1 d . . . . .
O4 O 0.17283(12) 0.27471(14) 0.66720(7) 0.0685(4) Uani 1 1 d . . . . .
N1 N 0.35981(11) 0.36352(12) 0.63744(7) 0.0468(3) Uani 1 1 d . . . . .
C1 C 0.39925(13) 0.24099(14) 0.51686(9) 0.0447(3) Uani 1 1 d . . . . .
C2 C 0.46476(16) 0.20485(16) 0.44833(10) 0.0572(4) Uani 1 1 d . . . . .
H2 H 0.436241 0.136989 0.409615 0.069 Uiso 1 1 calc R U . . .
C3 C 0.57407(18) 0.27131(19) 0.43793(12) 0.0677(5) Uani 1 1 d . . . . .
H3 H 0.618944 0.247765 0.391891 0.081 Uiso 1 1 calc R U . . .
C4 C 0.61633(17) 0.37152(19) 0.49515(12) 0.0673(5) Uani 1 1 d . . . . .
H4 H 0.689917 0.414560 0.487223 0.081 Uiso 1 1 calc R U . . .
C5 C 0.55159(15) 0.41008(16) 0.56464(11) 0.0563(4) Uani 1 1 d . . . . .
H5 H 0.580200 0.477959 0.603318 0.068 Uiso 1 1 calc R U . . .
C6 C 0.44316(13) 0.34325(14) 0.57365(9) 0.0446(3) Uani 1 1 d . . . . .
C7 C 0.26158(14) 0.27741(15) 0.62425(8) 0.0476(3) Uani 1 1 d . . . . .
C8 C 0.28708(14) 0.18338(13) 0.54854(9) 0.0447(3) Uani 1 1 d . . . . .
C9 C 0.33607(19) 0.06685(18) 0.57313(13) 0.0667(5) Uani 1 1 d . . . . .
H9A H 0.272472 0.039700 0.604099 0.100 Uiso 1 1 calc R U . . .
H9B H 0.416653 0.085009 0.603730 0.100 Uiso 1 1 calc R U . . .
H9C H 0.349488 0.003518 0.526828 0.100 Uiso 1 1 calc R U . . .
C10 C 0.16487(14) 0.14806(13) 0.49399(9) 0.0448(3) Uani 1 1 d . . . . .
H10A H 0.192066 0.099918 0.443808 0.054 Uiso 1 1 calc R U . . .
H10B H 0.111120 0.095165 0.516548 0.054 Uiso 1 1 calc R U . . .
C11 C 0.07936(13) 0.25187(13) 0.47752(8) 0.0426(3) Uani 1 1 d . . . . .
C12 C -0.00744(16) 0.20010(16) 0.40317(10) 0.0538(4) Uani 1 1 d . . . . .
C13 C -0.01099(15) 0.30822(15) 0.54465(9) 0.0502(3) Uani 1 1 d . . . . .
C14 C -0.2294(3) 0.1739(3) 0.65548(17) 0.1044(9) Uani 1 1 d . . . . .
H14A H -0.290864 0.146352 0.611786 0.157 Uiso 1 1 calc R U . . .
H14B H -0.275345 0.202633 0.702777 0.157 Uiso 1 1 calc R U . . .
H14C H -0.174451 0.107326 0.661399 0.157 Uiso 1 1 calc R U . . .
C15 C -0.1503(2) 0.27292(19) 0.64106(12) 0.0694(5) Uani 1 1 d . . . . .
H15A H -0.091659 0.304641 0.686380 0.083 Uiso 1 1 calc R U . . .
H15B H -0.205624 0.339021 0.632562 0.083 Uiso 1 1 calc R U . . .
C16 C 0.36744(14) 0.46567(14) 0.70417(8) 0.0461(3) Uani 1 1 d . . . . .
C17 C 0.45605(16) 0.46522(18) 0.76617(10) 0.0591(4) Uani 1 1 d . . . . .
H17 H 0.511853 0.399654 0.764433 0.071 Uiso 1 1 calc R U . . .
C18 C 0.4604(2) 0.5637(2) 0.83075(11) 0.0735(6) Uani 1 1 d . . . . .
H18 H 0.519402 0.564521 0.872897 0.088 Uiso 1 1 calc R U . . .
C19 C 0.3783(2) 0.6598(2) 0.83280(11) 0.0752(6) Uani 1 1 d . . . . .
H19 H 0.382405 0.726173 0.876189 0.090 Uiso 1 1 calc R U . . .
C20 C 0.2898(2) 0.65939(19) 0.77144(13) 0.0742(5) Uani 1 1 d . . . . .
H20 H 0.233857 0.724931 0.773400 0.089 Uiso 1 1 calc R U . . .
C21 C 0.28402(18) 0.56125(17) 0.70676(10) 0.0597(4) Uani 1 1 d . . . . .
H21 H 0.223779 0.560114 0.665182 0.072 Uiso 1 1 calc R U . . .
F4 F 0.52674(11) 0.07647(11) 0.75483(6) 0.0727(3) Uani 1 1 d . . . . .
F5 F 0.37901(11) -0.05768(10) 0.75139(6) 0.0748(3) Uani 1 1 d . . . . .
F6 F 0.55231(11) -0.05660(11) 0.82440(7) 0.0819(4) Uani 1 1 d . . . . .
O5 O 0.56776(9) 0.25205(10) 0.89945(6) 0.0488(2) Uani 1 1 d . . . . .
O6 O 0.53752(11) 0.13729(11) 0.98704(7) 0.0558(3) Uani 1 1 d . . . . .
O7 O 0.34022(10) 0.35034(10) 1.00176(6) 0.0498(3) Uani 1 1 d . . . . .
O8 O 0.32948(10) 0.02516(10) 0.90698(7) 0.0513(3) Uani 1 1 d . . . . .
H8 H 0.377085 0.004376 0.940440 0.077 Uiso 1 1 calc R U . . .
N2 N 0.14660(10) 0.25839(11) 1.02015(7) 0.0408(3) Uani 1 1 d . . . . .
C22 C 0.66561(15) 0.32987(16) 0.95116(11) 0.0581(4) Uani 1 1 d . . . . .
H22A H 0.708348 0.284638 0.986024 0.070 Uiso 1 1 calc R U . . .
H22B H 0.624488 0.400731 0.983202 0.070 Uiso 1 1 calc R U . . .
C23 C 0.76236(17) 0.36967(18) 0.90156(14) 0.0694(5) Uani 1 1 d . . . . .
H23A H 0.718966 0.412331 0.866217 0.104 Uiso 1 1 calc R U . . .
H23B H 0.805124 0.299256 0.871653 0.104 Uiso 1 1 calc R U . . .
H23C H 0.825655 0.423211 0.934682 0.104 Uiso 1 1 calc R U . . .
C24 C 0.50977(13) 0.16697(13) 0.92660(8) 0.0415(3) Uani 1 1 d . . . . .
C25 C 0.39982(13) 0.09976(13) 0.86898(8) 0.0405(3) Uani 1 1 d . . . . .
C26 C 0.46514(16) 0.01535(15) 0.79958(10) 0.0530(4) Uani 1 1 d . . . . .
C27 C 0.30863(13) 0.18595(14) 0.83622(8) 0.0420(3) Uani 1 1 d . . . . .
H27A H 0.268288 0.140142 0.786798 0.050 Uiso 1 1 calc R U . . .
H27B H 0.361219 0.250600 0.824358 0.050 Uiso 1 1 calc R U . . .
C28 C 0.20020(12) 0.24590(13) 0.88915(8) 0.0393(3) Uani 1 1 d . . . . .
C29 C 0.15477(16) 0.36145(15) 0.86221(10) 0.0530(4) Uani 1 1 d . . . . .
H29A H 0.082663 0.396615 0.892238 0.079 Uiso 1 1 calc R U . . .
H29B H 0.128307 0.339464 0.807226 0.079 Uiso 1 1 calc R U . . .
H29C H 0.225100 0.420053 0.870409 0.079 Uiso 1 1 calc R U . . .
C30 C 0.24280(12) 0.29046(12) 0.97593(8) 0.0392(3) Uani 1 1 d . . . . .
C31 C 0.08267(12) 0.16699(13) 0.89270(8) 0.0419(3) Uani 1 1 d . . . . .
C32 C 0.00663(15) 0.09217(16) 0.83396(10) 0.0549(4) Uani 1 1 d . . . . .
H32 H 0.028338 0.079258 0.781569 0.066 Uiso 1 1 calc R U . . .
C33 C -0.10375(16) 0.03588(17) 0.85425(12) 0.0630(4) Uani 1 1 d . . . . .
H33 H -0.155776 -0.015200 0.815115 0.076 Uiso 1 1 calc R U . . .
C34 C -0.13584(15) 0.05550(16) 0.93155(12) 0.0588(4) Uani 1 1 d . . . . .
H34 H -0.210314 0.018115 0.943848 0.071 Uiso 1 1 calc R U . . .
C35 C -0.05973(14) 0.12995(14) 0.99206(10) 0.0505(4) Uani 1 1 d . . . . .
H35 H -0.081740 0.142937 1.044410 0.061 Uiso 1 1 calc R U . . .
C36 C 0.05011(12) 0.18383(13) 0.97100(8) 0.0402(3) Uani 1 1 d . . . . .
C37 C 0.14883(14) 0.29670(13) 1.10419(8) 0.0423(3) Uani 1 1 d . . . . .
C38 C 0.04718(17) 0.36447(16) 1.14055(11) 0.0579(4) Uani 1 1 d . . . . .
H38 H -0.025150 0.381152 1.110969 0.070 Uiso 1 1 calc R U . . .
C39 C 0.0550(2) 0.40704(19) 1.22175(12) 0.0753(6) Uani 1 1 d . . . . .
H39 H -0.012397 0.453143 1.246921 0.090 Uiso 1 1 calc R U . . .
C40 C 0.1614(2) 0.3816(2) 1.26529(11) 0.0758(6) Uani 1 1 d . . . . .
H40 H 0.165884 0.410811 1.319762 0.091 Uiso 1 1 calc R U . . .
C41 C 0.2614(2) 0.31343(19) 1.22896(11) 0.0690(5) Uani 1 1 d . . . . .
H41 H 0.333070 0.296031 1.258774 0.083 Uiso 1 1 calc R U . . .
C42 C 0.25527(16) 0.27054(15) 1.14773(9) 0.0524(4) Uani 1 1 d . . . . .
H42 H 0.322787 0.224324 1.122825 0.063 Uiso 1 1 calc R U . . .
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C11 O1 H1 109.5 . . ?
C13 O3 C15 115.88(13) . . ?
C6 N1 C16 125.56(12) . . ?
C7 N1 C6 110.98(12) . . ?
C7 N1 C16 123.23(12) . . ?
C2 C1 C6 119.44(14) . . ?
C2 C1 C8 131.76(15) . . ?
C6 C1 C8 108.61(12) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.05(17) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.51(16) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.52(16) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 121.5 . . ?
C6 C5 C4 117.05(16) . . ?
C6 C5 H5 121.5 . . ?
C1 C6 N1 109.20(12) . . ?
C5 C6 N1 128.37(14) . . ?
C5 C6 C1 122.43(14) . . ?
O4 C7 N1 125.67(15) . . ?
O4 C7 C8 126.23(14) . . ?
N1 C7 C8 108.04(12) . . ?
C1 C8 C7 102.40(12) . . ?
C1 C8 C9 108.55(13) . . ?
C1 C8 C10 117.42(12) . . ?
C7 C8 C9 106.71(13) . . ?
C7 C8 C10 113.33(12) . . ?
C10 C8 C9 107.87(13) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 107.9 . . ?
C8 C10 H10B 107.9 . . ?
H10A C10 H10B 107.2 . . ?
C11 C10 C8 117.73(12) . . ?
C11 C10 H10A 107.9 . . ?
C11 C10 H10B 107.9 . . ?
O1 C11 C10 110.55(11) . . ?
O1 C11 C12 107.86(12) . . ?
O1 C11 C13 108.18(12) . . ?
C10 C11 C12 108.05(12) . . ?
C10 C11 C13 114.42(12) . . ?
C12 C11 C13 107.56(12) . . ?
F1 C12 F2 106.76(13) . . ?
F1 C12 C11 111.71(13) . . ?
F2 C12 C11 111.25(14) . . ?
F3 C12 F1 106.46(14) . . ?
F3 C12 F2 107.52(14) . . ?
F3 C12 C11 112.80(13) . . ?
O2 C13 O3 125.77(15) . . ?
O2 C13 C11 120.80(14) . . ?
O3 C13 C11 113.40(13) . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
O3 C15 H15A 109.9 . . ?
O3 C15 H15B 109.9 . . ?
C14 C15 O3 108.79(17) . . ?
C14 C15 H15A 109.9 . . ?
C14 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C17 C16 N1 119.83(15) . . ?
C21 C16 N1 119.37(13) . . ?
C21 C16 C17 120.77(15) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 119.01(18) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.16(18) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.61(18) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.8(2) . . ?
C21 C20 H20 120.1 . . ?
C16 C21 C20 119.66(17) . . ?
C16 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C24 O5 C22 117.83(12) . . ?
C25 O8 H8 109.5 . . ?
C30 N2 C36 110.78(11) . . ?
C30 N2 C37 122.81(11) . . ?
C36 N2 C37 126.41(11) . . ?
O5 C22 H22A 110.0 . . ?
O5 C22 H22B 110.0 . . ?
O5 C22 C23 108.52(15) . . ?
H22A C22 H22B 108.4 . . ?
C23 C22 H22A 110.0 . . ?
C23 C22 H22B 110.0 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O5 C24 C25 112.31(12) . . ?
O6 C24 O5 126.65(14) . . ?
O6 C24 C25 120.98(13) . . ?
O8 C25 C24 108.85(11) . . ?
O8 C25 C26 107.49(12) . . ?
O8 C25 C27 110.75(11) . . ?
C26 C25 C24 107.28(11) . . ?
C27 C25 C24 113.79(11) . . ?
C27 C25 C26 108.43(11) . . ?
F4 C26 C25 113.09(13) . . ?
F5 C26 F4 105.92(14) . . ?
F5 C26 F6 107.03(14) . . ?
F5 C26 C25 111.83(13) . . ?
F6 C26 F4 107.06(13) . . ?
F6 C26 C25 111.51(13) . . ?
C25 C27 H27A 108.1 . . ?
C25 C27 H27B 108.1 . . ?
C25 C27 C28 116.84(11) . . ?
H27A C27 H27B 107.3 . . ?
C28 C27 H27A 108.1 . . ?
C28 C27 H27B 108.1 . . ?
C27 C28 C29 108.51(11) . . ?
C30 C28 C27 114.31(11) . . ?
C30 C28 C29 105.48(12) . . ?
C31 C28 C27 116.77(12) . . ?
C31 C28 C29 108.80(11) . . ?
C31 C28 C30 102.27(11) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O7 C30 N2 125.87(13) . . ?
O7 C30 C28 126.04(12) . . ?
N2 C30 C28 107.95(11) . . ?
C32 C31 C28 131.25(14) . . ?
C32 C31 C36 119.85(14) . . ?
C36 C31 C28 108.82(12) . . ?
C31 C32 H32 120.5 . . ?
C31 C32 C33 118.96(16) . . ?
C33 C32 H32 120.5 . . ?
C32 C33 H33 119.8 . . ?
C34 C33 C32 120.39(16) . . ?
C34 C33 H33 119.8 . . ?
C33 C34 H34 119.2 . . ?
C33 C34 C35 121.67(15) . . ?
C35 C34 H34 119.2 . . ?
C34 C35 H35 121.4 . . ?
C36 C35 C34 117.17(15) . . ?
C36 C35 H35 121.4 . . ?
C31 C36 N2 109.12(12) . . ?
C35 C36 N2 128.93(13) . . ?
C35 C36 C31 121.94(14) . . ?
C38 C37 N2 119.81(14) . . ?
C42 C37 N2 119.32(12) . . ?
C42 C37 C38 120.80(14) . . ?
C37 C38 H38 120.6 . . ?
C37 C38 C39 118.87(18) . . ?
C39 C38 H38 120.6 . . ?
C38 C39 H39 119.8 . . ?
C40 C39 C38 120.43(18) . . ?
C40 C39 H39 119.8 . . ?
C39 C40 H40 119.8 . . ?
C41 C40 C39 120.41(17) . . ?
C41 C40 H40 119.8 . . ?
C40 C41 H41 120.1 . . ?
C40 C41 C42 119.86(19) . . ?
C42 C41 H41 120.1 . . ?
C37 C42 C41 119.62(16) . . ?
C37 C42 H42 120.2 . . ?
C41 C42 H42 120.2 . . ?
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
F1 C12 1.328(2) . ?
F2 C12 1.332(2) . ?
F3 C12 1.326(2) . ?
O1 H1 0.8200 . ?
O1 C11 1.4005(17) . ?
O2 C13 1.202(2) . ?
O3 C13 1.3152(19) . ?
O3 C15 1.469(2) . ?
O4 C7 1.2126(18) . ?
N1 C6 1.4136(19) . ?
N1 C7 1.3710(19) . ?
N1 C16 1.4314(19) . ?
C1 C2 1.378(2) . ?
C1 C6 1.390(2) . ?
C1 C8 1.509(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(2) . ?
C7 C8 1.521(2) . ?
C8 C9 1.547(2) . ?
C8 C10 1.535(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.533(2) . ?
C11 C12 1.536(2) . ?
C11 C13 1.548(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 C15 1.451(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.383(2) . ?
C16 C21 1.369(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.367(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.381(3) . ?
C21 H21 0.9300 . ?
F4 C26 1.333(2) . ?
F5 C26 1.331(2) . ?
F6 C26 1.3315(19) . ?
O5 C22 1.4619(19) . ?
O5 C24 1.3142(17) . ?
O6 C24 1.2007(18) . ?
O7 C30 1.2141(17) . ?
O8 H8 0.8200 . ?
O8 C25 1.4019(17) . ?
N2 C30 1.3796(17) . ?
N2 C36 1.4165(18) . ?
N2 C37 1.4288(18) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.483(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.5489(19) . ?
C25 C26 1.537(2) . ?
C25 C27 1.5341(19) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.5361(18) . ?
C28 C29 1.545(2) . ?
C28 C30 1.5240(19) . ?
C28 C31 1.5095(19) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C31 C32 1.375(2) . ?
C31 C36 1.392(2) . ?
C32 H32 0.9300 . ?
C32 C33 1.397(2) . ?
C33 H33 0.9300 . ?
C33 C34 1.372(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.392(2) . ?
C35 H35 0.9300 . ?
C35 C36 1.385(2) . ?
C37 C38 1.384(2) . ?
C37 C42 1.375(2) . ?
C38 H38 0.9300 . ?
C38 C39 1.385(3) . ?
C39 H39 0.9300 . ?
C39 C40 1.372(3) . ?
C40 H40 0.9300 . ?
C40 C41 1.372(3) . ?
C41 H41 0.9300 . ?
C41 C42 1.386(2) . ?
C42 H42 0.9300 . ?
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
O1 C11 C12 F1 55.62(17) . . . . ?
O1 C11 C12 F2 -63.57(16) . . . . ?
O1 C11 C12 F3 175.50(13) . . . . ?
O1 C11 C13 O2 10.7(2) . . . . ?
O1 C11 C13 O3 -171.30(12) . . . . ?
O4 C7 C8 C1 174.13(16) . . . . ?
O4 C7 C8 C9 -71.9(2) . . . . ?
O4 C7 C8 C10 46.7(2) . . . . ?
N1 C7 C8 C1 -8.39(15) . . . . ?
N1 C7 C8 C9 105.57(15) . . . . ?
N1 C7 C8 C10 -135.85(13) . . . . ?
N1 C16 C17 C18 -178.85(16) . . . . ?
N1 C16 C21 C20 179.18(16) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C1 C8 C10 C11 -71.46(17) . . . . ?
C2 C1 C6 N1 178.94(14) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C2 C1 C8 C7 -176.84(16) . . . . ?
C2 C1 C8 C9 70.6(2) . . . . ?
C2 C1 C8 C10 -52.0(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 N1 -179.15(16) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C6 N1 C7 O4 -176.85(16) . . . . ?
C6 N1 C7 C8 5.65(17) . . . . ?
C6 N1 C16 C17 -81.5(2) . . . . ?
C6 N1 C16 C21 100.35(18) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
C6 C1 C8 C7 8.34(15) . . . . ?
C6 C1 C8 C9 -104.26(15) . . . . ?
C6 C1 C8 C10 133.15(13) . . . . ?
C7 N1 C6 C1 -0.14(17) . . . . ?
C7 N1 C6 C5 179.53(15) . . . . ?
C7 N1 C16 C17 104.45(18) . . . . ?
C7 N1 C16 C21 -73.7(2) . . . . ?
C7 C8 C10 C11 47.70(18) . . . . ?
C8 C1 C2 C3 -173.90(16) . . . . ?
C8 C1 C6 N1 -5.49(16) . . . . ?
C8 C1 C6 C5 174.81(14) . . . . ?
C8 C10 C11 O1 43.86(17) . . . . ?
C8 C10 C11 C12 161.68(13) . . . . ?
C8 C10 C11 C13 -78.56(16) . . . . ?
C9 C8 C10 C11 165.60(14) . . . . ?
C10 C11 C12 F1 -63.91(16) . . . . ?
C10 C11 C12 F2 176.90(13) . . . . ?
C10 C11 C12 F3 55.97(17) . . . . ?
C10 C11 C13 O2 134.41(16) . . . . ?
C10 C11 C13 O3 -47.60(17) . . . . ?
C12 C11 C13 O2 -105.55(18) . . . . ?
C12 C11 C13 O3 72.44(16) . . . . ?
C13 O3 C15 C14 171.89(19) . . . . ?
C13 C11 C12 F1 172.09(13) . . . . ?
C13 C11 C12 F2 52.90(17) . . . . ?
C13 C11 C12 F3 -68.03(17) . . . . ?
C15 O3 C13 O2 -9.3(2) . . . . ?
C15 O3 C13 C11 172.81(14) . . . . ?
C16 N1 C6 C1 -174.79(14) . . . . ?
C16 N1 C6 C5 4.9(2) . . . . ?
C16 N1 C7 O4 -2.1(3) . . . . ?
C16 N1 C7 C8 -179.56(13) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C17 C16 C21 C20 1.1(3) . . . . ?
C17 C18 C19 C20 0.7(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C16 -0.5(3) . . . . ?
C21 C16 C17 C18 -0.8(3) . . . . ?
O5 C24 C25 O8 -170.59(11) . . . . ?
O5 C24 C25 C26 73.39(14) . . . . ?
O5 C24 C25 C27 -46.55(15) . . . . ?
O6 C24 C25 O8 11.99(18) . . . . ?
O6 C24 C25 C26 -104.04(15) . . . . ?
O6 C24 C25 C27 136.03(14) . . . . ?
O8 C25 C26 F4 174.93(12) . . . . ?
O8 C25 C26 F5 55.45(16) . . . . ?
O8 C25 C26 F6 -64.36(16) . . . . ?
O8 C25 C27 C28 41.71(17) . . . . ?
N2 C37 C38 C39 -176.11(15) . . . . ?
N2 C37 C42 C41 176.34(15) . . . . ?
C22 O5 C24 O6 -8.1(2) . . . . ?
C22 O5 C24 C25 174.63(11) . . . . ?
C24 O5 C22 C23 150.85(14) . . . . ?
C24 C25 C26 F4 -68.15(16) . . . . ?
C24 C25 C26 F5 172.37(13) . . . . ?
C24 C25 C26 F6 52.57(17) . . . . ?
C24 C25 C27 C28 -81.30(15) . . . . ?
C25 C27 C28 C29 158.87(13) . . . . ?
C25 C27 C28 C30 41.49(17) . . . . ?
C25 C27 C28 C31 -77.79(15) . . . . ?
C26 C25 C27 C28 159.42(12) . . . . ?
C27 C25 C26 F4 55.15(17) . . . . ?
C27 C25 C26 F5 -64.33(16) . . . . ?
C27 C25 C26 F6 175.87(13) . . . . ?
C27 C28 C30 O7 47.18(19) . . . . ?
C27 C28 C30 N2 -137.06(12) . . . . ?
C27 C28 C31 C32 -48.1(2) . . . . ?
C27 C28 C31 C36 135.28(12) . . . . ?
C28 C31 C32 C33 -175.27(15) . . . . ?
C28 C31 C36 N2 -6.25(15) . . . . ?
C28 C31 C36 C35 175.20(12) . . . . ?
C29 C28 C30 O7 -71.93(16) . . . . ?
C29 C28 C30 N2 103.83(12) . . . . ?
C29 C28 C31 C32 75.10(19) . . . . ?
C29 C28 C31 C36 -101.54(13) . . . . ?
C30 N2 C36 C31 -0.43(15) . . . . ?
C30 N2 C36 C35 177.99(13) . . . . ?
C30 N2 C37 C38 121.15(16) . . . . ?
C30 N2 C37 C42 -55.78(19) . . . . ?
C30 C28 C31 C32 -173.64(15) . . . . ?
C30 C28 C31 C36 9.72(14) . . . . ?
C31 C28 C30 O7 174.34(13) . . . . ?
C31 C28 C30 N2 -9.90(13) . . . . ?
C31 C32 C33 C34 0.3(3) . . . . ?
C32 C31 C36 N2 176.67(13) . . . . ?
C32 C31 C36 C35 -1.9(2) . . . . ?
C32 C33 C34 C35 -0.9(3) . . . . ?
C33 C34 C35 C36 0.1(2) . . . . ?
C34 C35 C36 N2 -176.96(14) . . . . ?
C34 C35 C36 C31 1.3(2) . . . . ?
C36 N2 C30 O7 -177.41(13) . . . . ?
C36 N2 C30 C28 6.82(14) . . . . ?
C36 N2 C37 C38 -59.38(19) . . . . ?
C36 N2 C37 C42 123.69(15) . . . . ?
C36 C31 C32 C33 1.1(2) . . . . ?
C37 N2 C30 O7 2.1(2) . . . . ?
C37 N2 C30 C28 -173.64(11) . . . . ?
C37 N2 C36 C31 -179.95(12) . . . . ?
C37 N2 C36 C35 -1.5(2) . . . . ?
C37 C38 C39 C40 -0.4(3) . . . . ?
C38 C37 C42 C41 -0.6(2) . . . . ?
C38 C39 C40 C41 -0.2(3) . . . . ?
C39 C40 C41 C42 0.4(3) . . . . ?
C40 C41 C42 C37 0.0(3) . . . . ?
C42 C37 C38 C39 0.8(3) . . . . ?
