#------------------------------------------------------------------------------
#$Date: 2023-05-23 01:57:06 +0300 (Tue, 23 May 2023) $
#$Revision: 283948 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/31/7713120.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_7713120
loop_
_publ_author_name
'Kong, Lingyu'
'Chou, Yajie'
'ALBALAT, Muriel'
'Jean, Marion'
'Vanthuyne, Nicolas'
'Nava, Paola'
'Humbel, Stéphane'
'Clavier, Hervé'
_publ_section_title
;
 C2-Symmetric Atropisomeric N-Heterocyclic Carbene-Palladium(II)
 Complexes: Synthesis, Chiral Resolution and Application in
 enantioselective α-Arylation of Amides
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT01182H
_journal_year                    2023
_chemical_formula_moiety         'C45 H39 F2 N2, B F4'
_chemical_formula_sum            'C45 H38 B F6 N2'
_chemical_formula_weight         731.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-02-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-20 deposited with the CCDC.	2023-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.570(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4939(14)
_cell_length_b                   17.6838(6)
_cell_length_c                   16.9141(11)
_cell_measurement_reflns_used    1829
_cell_measurement_temperature    295
_cell_measurement_theta_max      66.8010
_cell_measurement_theta_min      3.8730
_cell_volume                     4332.7(6)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     68.00 103.00   1.00    2.50    --    0.00 178.00   0.00   35
  2  ω     36.00  91.00   1.00    2.50    --    0.00  57.00 -90.00   55
  3  ω     58.00  90.00   1.00    2.50    --    0.00 178.00 -90.00   32
  4  ω    -15.00  20.00   1.00    2.50    --    0.00  57.00 -90.00   35
  5  ω   -151.00 -80.00   1.00    2.50    --  -53.50 -94.00  30.00   71
  6  ω   -133.00 -82.00   1.00    2.50    --  -53.50 -94.00 120.00   51
  7  ω   -134.00 -86.00   1.00    2.50    --  -53.50 -94.00 -30.00   48
  8  ω    107.00 149.00   1.00    2.50    --   53.50 125.00  30.00   42
  9  ω     94.00 149.00   1.00    2.50    --   53.50 125.00-180.00   55
 10  ω     97.00 124.00   1.00    2.50    --   53.50 125.00 -30.00   27
 11  ω     95.00 149.00   1.00    2.50    --   53.50 125.00  90.00   54
 12  ω     61.00 174.00   1.00   45.00    --  107.00  38.00 -30.00  113
 13  ω    142.00 176.00   1.00   45.00    --  107.00  38.00 150.00   34
 14  ω     61.00  86.00   1.00   45.00    --  107.00  38.00 150.00   25
 15  ω    148.00 175.00   1.00   45.00    --  107.00  77.00 120.00   27
 16  ω     73.00 100.00   1.00   45.00    --  107.00  77.00 120.00   27
 17  ω    109.00 137.00   1.00   45.00    --  107.00 111.00 -30.00   28
 18  ω     12.00 153.00   1.00   45.00    --  107.00 -50.00 120.00  141
 19  ω     12.00  82.00   1.00   45.00    --  107.00-111.00 120.00   70
 20  ω     51.00 139.00   1.00   45.00    --  107.00 -63.00-150.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0493606000
_diffrn_orient_matrix_UB_12      -0.0634116000
_diffrn_orient_matrix_UB_13      0.0229570000
_diffrn_orient_matrix_UB_21      -0.0854441000
_diffrn_orient_matrix_UB_22      0.0090932000
_diffrn_orient_matrix_UB_23      -0.0932881000
_diffrn_orient_matrix_UB_31      0.0399032000
_diffrn_orient_matrix_UB_32      -0.0589756000
_diffrn_orient_matrix_UB_33      -0.0390167000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.1139
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14465
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.234
_diffrn_reflns_theta_min         3.051
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_description       plate
_exptl_crystal_F_000             1524
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         7751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1782
_refine_ls_R_factor_gt           0.0986
_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)+(0.1498P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2795
_refine_ls_wR_factor_ref         0.3322
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3173
_reflns_number_total             7751
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt01182h2.cif
_cod_data_source_block           lk4077diamaj
_cod_database_code               7713120
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c45 h33 b1 f6 n2'
_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   0.986
_shelx_estimated_absorpt_t_min   0.820
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C32(H32)
2.b Aromatic/amide H refined with riding coordinates:
 C4AA(H4AA), C8(H8), C10(H10), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C28(H28), C30(H30),
  C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C40(H40), C41(H41),
 C42(H42), C43(H43), C44(H44)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C25(H25A,H25B,H25C), C45(H45A,H45B,H45C)
;
_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 1.573
_oxdiff_exptl_absorpt_empirical_full_min 0.609
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
F1 F 0.5510(3) 0.3481(3) 0.5914(2) 0.1004(14) Uani 1 1 d . . . . .
F2 F 0.5511(3) 0.1166(3) 0.2677(3) 0.0909(12) Uani 1 1 d . . . . .
N1 N 0.5004(3) 0.2735(3) 0.4370(3) 0.0568(11) Uani 1 1 d . . . . .
N2 N 0.5945(3) 0.2026(2) 0.4150(3) 0.0553(11) Uani 1 1 d . . . . .
C2 C 0.5601(5) 0.1596(3) 0.4605(4) 0.0648(14) Uani 1 1 d . . . . .
C3 C 0.5033(4) 0.2025(4) 0.4768(4) 0.0655(14) Uani 1 1 d . . . . .
C4 C 0.5888(5) 0.0796(4) 0.4869(5) 0.0804(19) Uani 1 1 d . . . . .
H4A H 0.564437 0.048519 0.433973 0.121 Uiso 1 1 calc GR . . . .
H4B H 0.565520 0.062394 0.526015 0.121 Uiso 1 1 calc GR . . . .
H4C H 0.654974 0.076507 0.517695 0.121 Uiso 1 1 calc GR . . . .
C4AA C 0.5557(4) 0.2716(3) 0.4019(4) 0.0565(13) Uani 1 1 d . . . . .
H4AA H 0.566570 0.311562 0.372506 0.068 Uiso 1 1 calc R . . . .
C5 C 0.4490(6) 0.1870(5) 0.5255(5) 0.096(2) Uani 1 1 d . . . . .
H5A H 0.485943 0.199240 0.588087 0.144 Uiso 1 1 calc GR . . . .
H5B H 0.432461 0.134421 0.519557 0.144 Uiso 1 1 calc GR . . . .
H5C H 0.394089 0.217297 0.500021 0.144 Uiso 1 1 calc GR . . . .
C6 C 0.4482(4) 0.3390(3) 0.4375(4) 0.0591(13) Uani 1 1 d . . . . .
C7 C 0.4749(5) 0.3756(4) 0.5175(4) 0.0756(18) Uani 1 1 d . . . . .
C8 C 0.4315(5) 0.4381(4) 0.5273(4) 0.0801(19) Uani 1 1 d . . . . .
H8 H 0.452221 0.461781 0.582679 0.096 Uiso 1 1 calc R . . . .
C9 C 0.3562(5) 0.4640(4) 0.4516(5) 0.0734(17) Uani 1 1 d . . . . .
C10 C 0.3283(5) 0.4301(3) 0.3686(4) 0.0641(15) Uani 1 1 d . . . . .
H10 H 0.279101 0.451092 0.317909 0.077 Uiso 1 1 calc R . . . .
C11 C 0.3710(4) 0.3662(3) 0.3584(4) 0.0594(13) Uani 1 1 d . . . . .
C12 C 0.3421(5) 0.3281(3) 0.2682(4) 0.0670(15) Uani 1 1 d . . . . .
H12 H 0.395733 0.331385 0.258034 0.080 Uiso 1 1 calc R . . . .
C13 C 0.2631(5) 0.3693(3) 0.1883(4) 0.0687(15) Uani 1 1 d . . . . .
C14 C 0.2862(6) 0.4149(4) 0.1357(5) 0.091(2) Uani 1 1 d . . . . .
H14 H 0.347610 0.421618 0.150142 0.109 Uiso 1 1 calc R . . . .
C15 C 0.2161(8) 0.4504(5) 0.0611(6) 0.109(3) Uani 1 1 d . . . . .
H15 H 0.231289 0.480183 0.024707 0.131 Uiso 1 1 calc R . . . .
C16 C 0.1276(8) 0.4428(5) 0.0403(6) 0.113(3) Uani 1 1 d . . . . .
H16 H 0.081632 0.467308 -0.009791 0.136 Uiso 1 1 calc R . . . .
C17 C 0.1056(7) 0.3994(5) 0.0925(7) 0.110(3) Uani 1 1 d . . . . .
H17 H 0.044163 0.394729 0.078860 0.132 Uiso 1 1 calc R . . . .
C18 C 0.1738(5) 0.3613(4) 0.1668(5) 0.091(2) Uani 1 1 d . . . . .
H18 H 0.157477 0.330403 0.201419 0.109 Uiso 1 1 calc R . . . .
C19 C 0.3228(5) 0.2443(4) 0.2694(5) 0.0796(19) Uani 1 1 d . . . . .
C20 C 0.3561(7) 0.1942(4) 0.2299(7) 0.110(3) Uani 1 1 d . . . . .
H20 H 0.389544 0.212669 0.202726 0.132 Uiso 1 1 calc R . . . .
C21 C 0.3417(8) 0.1179(6) 0.2292(10) 0.140(5) Uani 1 1 d . . . . .
H21 H 0.362711 0.084738 0.200335 0.168 Uiso 1 1 calc R . . . .
C22 C 0.2960(8) 0.0927(5) 0.2719(10) 0.133(4) Uani 1 1 d . . . . .
H22 H 0.288509 0.040813 0.274353 0.159 Uiso 1 1 calc R . . . .
C23 C 0.2602(6) 0.1388(6) 0.3117(9) 0.137(4) Uani 1 1 d . . . . .
H23 H 0.227816 0.119086 0.339308 0.164 Uiso 1 1 calc R . . . .
C24 C 0.2739(6) 0.2192(5) 0.3098(7) 0.106(3) Uani 1 1 d . . . . .
H24 H 0.249914 0.252849 0.335581 0.128 Uiso 1 1 calc R . . . .
C25 C 0.3047(6) 0.5326(4) 0.4572(5) 0.095(2) Uani 1 1 d . . . . .
H25A H 0.318171 0.540124 0.518476 0.143 Uiso 1 1 calc GR . . . .
H25B H 0.239534 0.524894 0.420148 0.143 Uiso 1 1 calc GR . . . .
H25C H 0.323604 0.576264 0.436505 0.143 Uiso 1 1 calc GR . . . .
C26 C 0.6635(4) 0.1822(3) 0.3913(3) 0.0505(12) Uani 1 1 d . . . . .
C27 C 0.6402(4) 0.1381(3) 0.3153(4) 0.0659(15) Uani 1 1 d . . . . .
C28 C 0.7027(5) 0.1163(4) 0.2889(4) 0.0724(17) Uani 1 1 d . . . . .
H28 H 0.684780 0.086568 0.237858 0.087 Uiso 1 1 calc R . . . .
C29 C 0.7938(5) 0.1393(4) 0.3399(4) 0.0693(16) Uani 1 1 d . . . . .
C30 C 0.8177(5) 0.1844(3) 0.4151(4) 0.0648(15) Uani 1 1 d . . . . .
H30 H 0.878393 0.200799 0.448291 0.078 Uiso 1 1 calc R . . . .
C31 C 0.7545(4) 0.2053(3) 0.4419(3) 0.0520(12) Uani 1 1 d . . . . .
C32 C 0.7841(4) 0.2491(3) 0.5295(4) 0.0630(14) Uani 1 1 d . . . . .
H32 H 0.731779 0.281811 0.518597 0.076 Uiso 1 1 calc R . . . .
C33 C 0.8656(5) 0.3022(3) 0.5538(4) 0.0652(15) Uani 1 1 d . . . . .
C34 C 0.8540(6) 0.3631(4) 0.4993(5) 0.085(2) Uani 1 1 d . . . . .
H34 H 0.798465 0.369936 0.446781 0.102 Uiso 1 1 calc R . . . .
C35 C 0.9261(8) 0.4151(5) 0.5230(7) 0.108(3) Uani 1 1 d . . . . .
H35 H 0.917170 0.457542 0.487251 0.130 Uiso 1 1 calc R . . . .
C36 C 1.0087(8) 0.4042(7) 0.5973(8) 0.134(4) Uani 1 1 d . . . . .
H36 H 1.057368 0.437522 0.611375 0.161 Uiso 1 1 calc R . . . .
C37 C 1.0191(8) 0.3449(7) 0.6500(8) 0.145(5) Uani 1 1 d . . . . .
H37 H 1.075319 0.337794 0.701647 0.173 Uiso 1 1 calc R . . . .
C38 C 0.9489(6) 0.2939(5) 0.6300(6) 0.104(3) Uani 1 1 d . . . . .
H38 H 0.958162 0.253508 0.668560 0.125 Uiso 1 1 calc R . . . .
C39 C 0.7961(5) 0.1969(4) 0.6041(4) 0.0682(16) Uani 1 1 d . . . . .
C40 C 0.7585(6) 0.2145(5) 0.6589(5) 0.096(2) Uani 1 1 d . . . . .
H40 H 0.724887 0.259102 0.648126 0.115 Uiso 1 1 calc R . . . .
C41 C 0.7685(10) 0.1685(7) 0.7297(7) 0.135(5) Uani 1 1 d . . . . .
H41 H 0.743186 0.182045 0.766398 0.163 Uiso 1 1 calc R . . . .
C42 C 0.8165(9) 0.1031(7) 0.7435(6) 0.138(5) Uani 1 1 d . . . . .
H42 H 0.822287 0.071356 0.789750 0.165 Uiso 1 1 calc R . . . .
C43 C 0.8580(8) 0.0811(6) 0.6915(6) 0.124(4) Uani 1 1 d . . . . .
H43 H 0.891999 0.036721 0.703278 0.149 Uiso 1 1 calc R . . . .
C44 C 0.8453(6) 0.1300(4) 0.6200(5) 0.092(2) Uani 1 1 d . . . . .
H44 H 0.870505 0.116952 0.583052 0.110 Uiso 1 1 calc R . . . .
C45 C 0.8649(6) 0.1156(5) 0.3120(5) 0.093(2) Uani 1 1 d . . . . .
H45A H 0.889831 0.067186 0.337745 0.139 Uiso 1 1 calc GR . . . .
H45B H 0.913653 0.152339 0.333097 0.139 Uiso 1 1 calc GR . . . .
H45C H 0.836106 0.112394 0.247580 0.139 Uiso 1 1 calc GR . . . .
F3 F 0.5502(5) 0.4516(3) 0.1828(3) 0.135(2) Uani 1 1 d . . . . .
F4 F 0.6614(5) 0.4327(5) 0.3202(4) 0.158(3) Uani 1 1 d . . . . .
F5 F 0.5615(6) 0.3406(3) 0.2457(4) 0.169(3) Uani 1 1 d . . . . .
F6 F 0.5225(4) 0.4383(3) 0.3012(4) 0.127(2) Uani 1 1 d . . . . .
B51 B 0.5706(8) 0.4180(5) 0.2581(6) 0.084(2) 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'
B B 0.0090 0.0039 '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_
_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
C3 N1 C6 126.4(4) . . ?
C4AA N1 C3 108.7(5) . . ?
C4AA N1 C6 124.8(5) . . ?
C2 N2 C26 128.0(5) . . ?
C4AA N2 C2 107.5(5) . . ?
C4AA N2 C26 124.4(4) . . ?
N2 C2 C4 122.1(6) . . ?
C3 C2 N2 108.6(5) . . ?
C3 C2 C4 129.2(6) . . ?
N1 C3 C5 121.9(6) . . ?
C2 C3 N1 105.9(5) . . ?
C2 C3 C5 132.2(6) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C4AA N2 109.3(5) . . ?
N1 C4AA H4AA 125.4 . . ?
N2 C4AA H4AA 125.4 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 N1 118.3(6) . . ?
C7 C6 C11 119.4(6) . . ?
C11 C6 N1 122.3(5) . . ?
C6 C7 F1 117.1(6) . . ?
C8 C7 F1 118.7(6) . . ?
C8 C7 C6 124.2(7) . . ?
C7 C8 H8 121.6 . . ?
C9 C8 C7 116.8(6) . . ?
C9 C8 H8 121.6 . . ?
C8 C9 C10 121.1(6) . . ?
C8 C9 C25 119.8(6) . . ?
C10 C9 C25 119.1(7) . . ?
C9 C10 H10 118.8 . . ?
C9 C10 C11 122.4(6) . . ?
C11 C10 H10 118.8 . . ?
C6 C11 C12 120.4(5) . . ?
C10 C11 C6 116.1(5) . . ?
C10 C11 C12 123.5(6) . . ?
C11 C12 H12 105.9 . . ?
C11 C12 C13 113.5(5) . . ?
C13 C12 H12 105.9 . . ?
C19 C12 C11 112.7(5) . . ?
C19 C12 H12 105.9 . . ?
C19 C12 C13 112.3(6) . . ?
C14 C13 C12 117.6(7) . . ?
C18 C13 C12 123.0(7) . . ?
C18 C13 C14 119.4(7) . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.0(9) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.5(9) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.2(9) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 120.9(10) . . ?
C18 C17 H17 119.5 . . ?
C13 C18 C17 119.9(9) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C12 119.3(7) . . ?
C24 C19 C12 120.3(7) . . ?
C24 C19 C20 120.4(8) . . ?
C19 C20 H20 118.9 . . ?
C21 C20 C19 122.2(11) . . ?
C21 C20 H20 118.9 . . ?
C20 C21 H21 121.3 . . ?
C22 C21 C20 117.5(11) . . ?
C22 C21 H21 121.3 . . ?
C21 C22 H22 118.1 . . ?
C21 C22 C23 123.7(10) . . ?
C23 C22 H22 118.1 . . ?
C22 C23 H23 120.9 . . ?
C22 C23 C24 118.1(11) . . ?
C24 C23 H23 120.9 . . ?
C19 C24 C23 118.0(11) . . ?
C19 C24 H24 121.0 . . ?
C23 C24 H24 121.0 . . ?
C9 C25 H25A 109.5 . . ?
C9 C25 H25B 109.5 . . ?
C9 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 N2 119.8(5) . . ?
C31 C26 N2 121.8(4) . . ?
C31 C26 C27 118.4(5) . . ?
F2 C27 C26 116.8(5) . . ?
F2 C27 C28 120.3(5) . . ?
C28 C27 C26 122.9(6) . . ?
C27 C28 H28 120.7 . . ?
C27 C28 C29 118.6(6) . . ?
C29 C28 H28 120.7 . . ?
C28 C29 C30 119.1(6) . . ?
C28 C29 C45 119.6(6) . . ?
C30 C29 C45 121.3(7) . . ?
C29 C30 H30 119.0 . . ?
C31 C30 C29 122.0(6) . . ?
C31 C30 H30 119.0 . . ?
C26 C31 C32 119.8(4) . . ?
C30 C31 C26 119.0(5) . . ?
C30 C31 C32 121.0(5) . . ?
C31 C32 H32 105.8 . . ?
C33 C32 C31 113.9(4) . . ?
C33 C32 H32 105.8 . . ?
C39 C32 C31 110.8(5) . . ?
C39 C32 H32 105.8 . . ?
C39 C32 C33 114.1(5) . . ?
C34 C33 C32 118.8(6) . . ?
C34 C33 C38 118.0(7) . . ?
C38 C33 C32 123.1(6) . . ?
C33 C34 H34 120.1 . . ?
C33 C34 C35 119.8(8) . . ?
C35 C34 H34 120.1 . . ?
C34 C35 H35 119.6 . . ?
C36 C35 C34 120.7(9) . . ?
C36 C35 H35 119.6 . . ?
C35 C36 H36 120.6 . . ?
C37 C36 C35 118.9(10) . . ?
C37 C36 H36 120.6 . . ?
C36 C37 H37 119.1 . . ?
C36 C37 C38 121.9(11) . . ?
C38 C37 H37 119.1 . . ?
C33 C38 C37 120.6(9) . . ?
C33 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C40 C39 C32 120.5(7) . . ?
C40 C39 C44 118.3(7) . . ?
C44 C39 C32 121.2(6) . . ?
C39 C40 H40 118.6 . . ?
C39 C40 C41 122.8(10) . . ?
C41 C40 H40 118.6 . . ?
C40 C41 H41 121.1 . . ?
C42 C41 C40 117.8(9) . . ?
C42 C41 H41 121.1 . . ?
C41 C42 H42 118.4 . . ?
C41 C42 C43 123.2(9) . . ?
C43 C42 H42 118.4 . . ?
C42 C43 H43 121.7 . . ?
C42 C43 C44 116.7(10) . . ?
C44 C43 H43 121.7 . . ?
C39 C44 C43 121.3(8) . . ?
C39 C44 H44 119.4 . . ?
C43 C44 H44 119.4 . . ?
C29 C45 H45A 109.5 . . ?
C29 C45 H45B 109.5 . . ?
C29 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
F3 B51 F4 109.8(7) . . ?
F3 B51 F5 110.3(7) . . ?
F3 B51 F6 117.5(9) . . ?
F4 B51 F5 107.6(9) . . ?
F6 B51 F4 103.9(7) . . ?
F6 B51 F5 107.1(7) . . ?
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 C7 1.369(8) . ?
F2 C27 1.348(7) . ?
N1 C3 1.415(7) . ?
N1 C4AA 1.306(7) . ?
N1 C6 1.446(7) . ?
N2 C2 1.382(7) . ?
N2 C4AA 1.346(7) . ?
N2 C26 1.422(6) . ?
C2 C3 1.332(9) . ?
C2 C4 1.491(8) . ?
C3 C5 1.504(8) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C4AA H4AA 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.369(9) . ?
C6 C11 1.418(8) . ?
C7 C8 1.368(9) . ?
C8 H8 0.9300 . ?
C8 C9 1.368(10) . ?
C9 C10 1.386(9) . ?
C9 C25 1.509(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(8) . ?
C11 C12 1.521(8) . ?
C12 H12 0.9800 . ?
C12 C13 1.541(9) . ?
C12 C19 1.517(8) . ?
C13 C14 1.380(10) . ?
C13 C18 1.346(10) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(11) . ?
C15 H15 0.9300 . ?
C15 C16 1.336(13) . ?
C16 H16 0.9300 . ?
C16 C17 1.344(13) . ?
C17 H17 0.9300 . ?
C17 C18 1.395(11) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(11) . ?
C19 C24 1.358(12) . ?
C20 H20 0.9300 . ?
C20 C21 1.369(13) . ?
C21 H21 0.9300 . ?
C21 C22 1.344(16) . ?
C22 H22 0.9300 . ?
C22 C23 1.358(16) . ?
C23 H23 0.9300 . ?
C23 C24 1.442(12) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.392(8) . ?
C26 C31 1.386(8) . ?
C27 C28 1.360(9) . ?
C28 H28 0.9300 . ?
C28 C29 1.388(9) . ?
C29 C30 1.389(9) . ?
C29 C45 1.517(9) . ?
C30 H30 0.9300 . ?
C30 C31 1.372(7) . ?
C31 C32 1.531(7) . ?
C32 H32 0.9800 . ?
C32 C33 1.525(8) . ?
C32 C39 1.498(8) . ?
C33 C34 1.370(9) . ?
C33 C38 1.371(10) . ?
C34 H34 0.9300 . ?
C34 C35 1.402(11) . ?
C35 H35 0.9300 . ?
C35 C36 1.355(15) . ?
C36 H36 0.9300 . ?
C36 C37 1.333(15) . ?
C37 H37 0.9300 . ?
C37 C38 1.375(12) . ?
C38 H38 0.9300 . ?
C39 C40 1.375(9) . ?
C39 C44 1.386(10) . ?
C40 H40 0.9300 . ?
C40 C41 1.392(13) . ?
C41 H41 0.9300 . ?
C41 C42 1.357(17) . ?
C42 H42 0.9300 . ?
C42 C43 1.403(15) . ?
C43 H43 0.9300 . ?
C43 C44 1.419(11) . ?
C44 H44 0.9300 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
F3 B51 1.295(9) . ?
F4 B51 1.382(12) . ?
F5 B51 1.382(10) . ?
F6 B51 1.358(10) . ?
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
F1 C7 C8 C9 179.6(7) . . . . ?
F2 C27 C28 C29 -179.8(6) . . . . ?
N1 C6 C7 F1 1.3(9) . . . . ?
N1 C6 C7 C8 -179.9(6) . . . . ?
N1 C6 C11 C10 -179.2(5) . . . . ?
N1 C6 C11 C12 -2.1(8) . . . . ?
N2 C2 C3 N1 2.1(7) . . . . ?
N2 C2 C3 C5 -178.0(7) . . . . ?
N2 C26 C27 F2 -0.1(7) . . . . ?
N2 C26 C27 C28 -179.7(5) . . . . ?
N2 C26 C31 C30 -179.5(5) . . . . ?
N2 C26 C31 C32 4.4(7) . . . . ?
C2 N2 C4AA N1 0.4(6) . . . . ?
C2 N2 C26 C27 81.0(7) . . . . ?
C2 N2 C26 C31 -99.1(7) . . . . ?
C3 N1 C4AA N2 0.8(7) . . . . ?
C3 N1 C6 C7 69.1(8) . . . . ?
C3 N1 C6 C11 -110.9(7) . . . . ?
C4 C2 C3 N1 179.9(6) . . . . ?
C4 C2 C3 C5 -0.2(13) . . . . ?
C4AA N1 C3 C2 -1.8(7) . . . . ?
C4AA N1 C3 C5 178.2(6) . . . . ?
C4AA N1 C6 C7 -108.3(7) . . . . ?
C4AA N1 C6 C11 71.7(8) . . . . ?
C4AA N2 C2 C3 -1.6(7) . . . . ?
C4AA N2 C2 C4 -179.6(6) . . . . ?
C4AA N2 C26 C27 -104.2(6) . . . . ?
C4AA N2 C26 C31 75.7(7) . . . . ?
C6 N1 C3 C2 -179.6(5) . . . . ?
C6 N1 C3 C5 0.5(10) . . . . ?
C6 N1 C4AA N2 178.6(5) . . . . ?
C6 C7 C8 C9 0.8(11) . . . . ?
C6 C11 C12 C13 -174.4(6) . . . . ?
C6 C11 C12 C19 56.5(8) . . . . ?
C7 C6 C11 C10 0.8(8) . . . . ?
C7 C6 C11 C12 177.9(6) . . . . ?
C7 C8 C9 C10 -2.8(11) . . . . ?
C7 C8 C9 C25 179.9(7) . . . . ?
C8 C9 C10 C11 3.9(10) . . . . ?
C9 C10 C11 C6 -2.8(9) . . . . ?
C9 C10 C11 C12 -179.8(6) . . . . ?
C10 C11 C12 C13 2.4(9) . . . . ?
C10 C11 C12 C19 -126.7(6) . . . . ?
C11 C6 C7 F1 -178.7(6) . . . . ?
C11 C6 C7 C8 0.1(10) . . . . ?
C11 C12 C13 C14 100.8(7) . . . . ?
C11 C12 C13 C18 -80.9(8) . . . . ?
C11 C12 C19 C20 -136.0(7) . . . . ?
C11 C12 C19 C24 43.4(10) . . . . ?
C12 C13 C14 C15 177.5(7) . . . . ?
C12 C13 C18 C17 -178.9(7) . . . . ?
C12 C19 C20 C21 179.5(9) . . . . ?
C12 C19 C24 C23 -177.9(8) . . . . ?
C13 C12 C19 C20 94.3(8) . . . . ?
C13 C12 C19 C24 -86.3(8) . . . . ?
C13 C14 C15 C16 1.5(14) . . . . ?
C14 C13 C18 C17 -0.6(11) . . . . ?
C14 C15 C16 C17 -0.4(15) . . . . ?
C15 C16 C17 C18 -1.2(15) . . . . ?
C16 C17 C18 C13 1.7(14) . . . . ?
C18 C13 C14 C15 -1.0(11) . . . . ?
C19 C12 C13 C14 -129.9(7) . . . . ?
C19 C12 C13 C18 48.4(9) . . . . ?
C19 C20 C21 C22 -2.4(18) . . . . ?
C20 C19 C24 C23 1.4(13) . . . . ?
C20 C21 C22 C23 3(2) . . . . ?
C21 C22 C23 C24 -1.5(19) . . . . ?
C22 C23 C24 C19 -0.8(15) . . . . ?
C24 C19 C20 C21 0.1(15) . . . . ?
C25 C9 C10 C11 -178.7(6) . . . . ?
C26 N2 C2 C3 173.8(5) . . . . ?
C26 N2 C2 C4 -4.2(9) . . . . ?
C26 N2 C4AA N1 -175.2(5) . . . . ?
C26 C27 C28 C29 -0.2(9) . . . . ?
C26 C31 C32 C33 -151.9(5) . . . . ?
C26 C31 C32 C39 77.9(7) . . . . ?
C27 C26 C31 C30 0.4(7) . . . . ?
C27 C26 C31 C32 -175.7(5) . . . . ?
C27 C28 C29 C30 -0.7(9) . . . . ?
C27 C28 C29 C45 179.9(6) . . . . ?
C28 C29 C30 C31 1.6(9) . . . . ?
C29 C30 C31 C26 -1.4(8) . . . . ?
C29 C30 C31 C32 174.6(5) . . . . ?
C30 C31 C32 C33 32.1(8) . . . . ?
C30 C31 C32 C39 -98.1(6) . . . . ?
C31 C26 C27 F2 180.0(5) . . . . ?
C31 C26 C27 C28 0.4(8) . . . . ?
C31 C32 C33 C34 66.1(7) . . . . ?
C31 C32 C33 C38 -117.0(7) . . . . ?
C31 C32 C39 C40 -132.9(6) . . . . ?
C31 C32 C39 C44 47.3(8) . . . . ?
C32 C33 C34 C35 176.3(6) . . . . ?
C32 C33 C38 C37 -177.9(9) . . . . ?
C32 C39 C40 C41 -179.2(8) . . . . ?
C32 C39 C44 C43 179.0(7) . . . . ?
C33 C32 C39 C40 97.0(7) . . . . ?
C33 C32 C39 C44 -82.8(8) . . . . ?
C33 C34 C35 C36 2.8(14) . . . . ?
C34 C33 C38 C37 -1.0(14) . . . . ?
C34 C35 C36 C37 -3.0(18) . . . . ?
C35 C36 C37 C38 1(2) . . . . ?
C36 C37 C38 C33 1(2) . . . . ?
C38 C33 C34 C35 -0.7(11) . . . . ?
C39 C32 C33 C34 -165.3(5) . . . . ?
C39 C32 C33 C38 11.5(9) . . . . ?
C39 C40 C41 C42 -1.0(15) . . . . ?
C40 C39 C44 C43 -0.8(12) . . . . ?
C40 C41 C42 C43 1.6(17) . . . . ?
C41 C42 C43 C44 -1.8(16) . . . . ?
C42 C43 C44 C39 1.4(13) . . . . ?
C44 C39 C40 C41 0.6(12) . . . . ?
C45 C29 C30 C31 -179.0(6) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.660 0.250 415.5 78.9 ?
2 0.000 -0.455 0.750 415.5 78.9 ?
