#------------------------------------------------------------------------------
#$Date: 2025-07-06 19:46:40 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 301097 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/05/7160524.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_7160524
loop_
_publ_author_name
'Min, Yang'
'Shen, Hanxiao'
'Huang, Shaoying'
'Gu, Haorui'
'Lin, Xufeng'
_publ_section_title
;
 Organocatalytic asymmetric synthesis of axially and centrally chiral
 heterotriarylmethanes by a Friedel-Crafts reaction.
;
_journal_issue                   22
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5359
_journal_page_last               5372
_journal_paper_doi               10.1039/d5ob00532a
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         '0.5(C H Cl3), C33 H27 F N2 O3'
_chemical_formula_sum            'C33.5 H27.5 Cl1.5 F N2 O3'
_chemical_formula_weight         578.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-09-19
_audit_creation_method
;
FinalCif V65 by Daniel Kratzert, Freiburg 2019,
https://github.com/dkratzert/FinalCif
;
_audit_update_record
;
2025-03-17 deposited with the CCDC.	2025-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.022(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5056(7)
_cell_length_b                   13.8298(8)
_cell_length_c                   18.2204(11)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.617
_cell_measurement_theta_min      4.263
_cell_volume                     2870.9(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III M28'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'ZJU Bruker D8 VENTURE Metaljet PHOTON III'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            47692
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.801
_diffrn_reflns_theta_min         4.264
_diffrn_source                   'liquid Metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.24954300000000001
_diffrn_source_type              'Bruker Excillum Metaljet D2+'
_diffrn_source_voltage           69.9
_exptl_absorpt_coefficient_mu    1.295
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1049 before and 0.0635 after correction.
The Ratio of minimum to maximum transmission is 0.9165.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             1204
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2792 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.097(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6564
_refine_ls_number_restraints     47
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0470
_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)+(0.0801P)²+1.4501P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1294
_reflns_Friedel_coverage         0.913
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                6203
_reflns_number_total             6564
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob00532a2.cif
_cod_data_source_block           240918_my0918_f1_tscl
_cod_depositor_comments          'Adding full bibliography for 7160524.cif.'
_cod_original_formula_sum        'C33.50 H27.50 Cl1.50 F N2 O3'
_cod_database_code               7160524
_shelx_shelxl_version_number     2019/2
_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_min   0.820
_shelx_estimated_absorpt_t_max   0.926
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C34-Cl1 \\sim C34-Cl2 \\sim C34-Cl3
 with sigma of 0.02
 Cl1-Cl2 \\sim Cl2-Cl3 \\sim Cl3-Cl1
 with sigma of 0.04
 C32-C33 \\sim C32-C33A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 1A
O3 \\sim C32 \\sim C33 \\sim C33A: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 2A
4. Rigid body (RIGU) restrains
 Cl1, Cl2, Cl3, C34
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H32C)=Sof(H32D)=Sof(C33A)=Sof(H33D)=Sof(H33E)=Sof(H33F)=1-FVAR(1)
 Sof(H32A)=Sof(H32B)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(H33C)=FVAR(1)
 Fixed Sof: Cl1(0.5) Cl2(0.5) Cl3(0.5) C34(0.5) H34(0.5)
6.a Ternary CH refined with riding coordinates:
 C34(H34), C20(H20)
6.b Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C32(H32C,H32D)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C1(H1A), C2(H2A), C3(H3), C4(H4), C7(H7), C8(H8), C16(H16),
 C17(H17), C18(H18), C19(H19), C22(H22), C24(H24), C25(H25), C26(H26), C28(H28),
  C30(H30)
6.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C33(H33A,H33B,H33C), C33A(H33D,H33E,H33F)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
Cl1 Cl 0.9655(8) 0.3921(4) 0.9404(4) 0.192(4) Uani 0.5 1 d D . P A -1
Cl2 Cl 1.0344(4) 0.5805(3) 0.9600(3) 0.1325(15) Uani 0.5 1 d D . P A -1
Cl3 Cl 1.0626(6) 0.4488(7) 1.0805(2) 0.196(4) Uani 0.5 1 d D . P A -1
C34 C 0.9580(7) 0.4864(6) 1.0026(4) 0.065(2) Uani 0.5 1 d D . P A -1
H34 H 0.877785 0.503132 1.013839 0.077 Uiso 0.5 1 calc R U P A -1
F1 F 0.81720(16) 0.31106(15) 0.79708(12) 0.0520(5) Uani 1 1 d . . . . .
O1 O 0.2684(2) 0.27392(15) 0.78823(13) 0.0479(5) Uani 1 1 d . . . . .
O2 O 0.6925(2) 0.60666(18) 0.49501(11) 0.0487(5) Uani 1 1 d . . . . .
O3 O 0.6731(3) 0.7653(2) 0.52069(16) 0.0678(8) Uani 1 1 d . U . . .
N1 N 0.27740(18) 0.52579(16) 0.65141(11) 0.0290(4) Uani 1 1 d . . . . .
H1 H 0.309906 0.548601 0.614030 0.035 Uiso 1 1 calc R U . . .
N2 N 0.5693(2) 0.72502(18) 0.64281(15) 0.0410(5) Uani 1 1 d . . . . .
H2 H 0.579138 0.787431 0.636546 0.049 Uiso 1 1 calc R U . . .
C1 C 0.3718(3) 0.5120(3) 1.03662(16) 0.0528(9) Uani 1 1 d . . . . .
H1A H 0.394286 0.484975 1.084424 0.063 Uiso 1 1 calc R U . . .
C2 C 0.3660(3) 0.6095(3) 1.02875(18) 0.0590(10) Uani 1 1 d . . . . .
H2A H 0.384064 0.650336 1.070719 0.071 Uiso 1 1 calc R U . . .
C3 C 0.3330(4) 0.6497(3) 0.9580(2) 0.0584(9) Uani 1 1 d . . . . .
H3 H 0.328467 0.717992 0.952553 0.070 Uiso 1 1 calc R U . . .
C4 C 0.3073(3) 0.5921(2) 0.89691(16) 0.0438(7) Uani 1 1 d . . . . .
H4 H 0.285342 0.620981 0.849706 0.053 Uiso 1 1 calc R U . . .
C5 C 0.3130(2) 0.4903(2) 0.90280(13) 0.0338(5) Uani 1 1 d . . . . .
C6 C 0.3449(2) 0.4497(3) 0.97478(14) 0.0410(7) Uani 1 1 d . . . . .
C7 C 0.3519(3) 0.3481(3) 0.98153(17) 0.0511(8) Uani 1 1 d . . . . .
H7 H 0.373558 0.320181 1.029125 0.061 Uiso 1 1 calc R U . . .
C8 C 0.3286(3) 0.2893(3) 0.92167(19) 0.0502(8) Uani 1 1 d . . . . .
H8 H 0.334073 0.221189 0.927702 0.060 Uiso 1 1 calc R U . . .
C9 C 0.2959(2) 0.3293(2) 0.85019(15) 0.0374(6) Uani 1 1 d . . . . .
C10 C 0.2890(2) 0.4287(2) 0.84021(13) 0.0297(5) Uani 1 1 d . . . . .
C11 C 0.3026(4) 0.1742(3) 0.7919(2) 0.0570(8) Uani 1 1 d . . . . .
H11A H 0.283158 0.144591 0.742832 0.085 Uiso 1 1 calc R U . . .
H11B H 0.260619 0.140320 0.827479 0.085 Uiso 1 1 calc R U . . .
H11C H 0.387324 0.169435 0.807837 0.085 Uiso 1 1 calc R U . . .
C12 C 0.2583(2) 0.46789(18) 0.76428(13) 0.0279(5) Uani 1 1 d . . . . .
C13 C 0.3361(2) 0.50210(18) 0.72019(12) 0.0274(4) Uani 1 1 d . . . . .
C14 C 0.1602(2) 0.50802(18) 0.65077(13) 0.0293(5) Uani 1 1 d . . . . .
C15 C 0.1445(2) 0.47064(18) 0.72084(13) 0.0277(5) Uani 1 1 d . . . . .
C16 C 0.0308(2) 0.4482(2) 0.73536(15) 0.0353(6) Uani 1 1 d . . . . .
H16 H 0.018555 0.421597 0.781720 0.042 Uiso 1 1 calc R U . . .
C17 C -0.0631(2) 0.4659(2) 0.68055(17) 0.0411(6) Uani 1 1 d . . . . .
H17 H -0.140545 0.452095 0.689940 0.049 Uiso 1 1 calc R U . . .
C18 C -0.0458(2) 0.5037(2) 0.61162(16) 0.0424(6) Uani 1 1 d . . . . .
H18 H -0.111777 0.514895 0.575106 0.051 Uiso 1 1 calc R U . . .
C19 C 0.0654(2) 0.5250(2) 0.59554(14) 0.0369(6) Uani 1 1 d . . . . .
H19 H 0.076812 0.550352 0.548612 0.044 Uiso 1 1 calc R U . . .
C20 C 0.4683(2) 0.51199(18) 0.73807(13) 0.0280(5) Uani 1 1 d . . . . .
H20 H 0.485656 0.535804 0.790268 0.034 Uiso 1 1 calc R U . . .
C21 C 0.5303(2) 0.41441(19) 0.73480(13) 0.0299(5) Uani 1 1 d . . . . .
C22 C 0.6468(2) 0.4058(2) 0.76828(14) 0.0328(5) Uani 1 1 d . . . . .
H22 H 0.686099 0.459019 0.793668 0.039 Uiso 1 1 calc R U . . .
C23 C 0.7036(2) 0.3187(2) 0.76382(15) 0.0364(5) Uani 1 1 d . . . . .
C24 C 0.6529(3) 0.2397(2) 0.72770(18) 0.0429(6) Uani 1 1 d . . . . .
H24 H 0.695241 0.181111 0.725154 0.051 Uiso 1 1 calc R U . . .
C25 C 0.5367(3) 0.2482(2) 0.6947(2) 0.0487(7) Uani 1 1 d . . . . .
H25 H 0.498307 0.194435 0.669463 0.058 Uiso 1 1 calc R U . . .
C26 C 0.4766(2) 0.3348(2) 0.69841(17) 0.0392(6) Uani 1 1 d . . . . .
H26 H 0.397284 0.339439 0.675641 0.047 Uiso 1 1 calc R U . . .
C27 C 0.5180(2) 0.58508(19) 0.68958(13) 0.0288(5) Uani 1 1 d . . . . .
C28 C 0.5193(3) 0.6843(2) 0.69826(16) 0.0386(6) Uani 1 1 d . . . . .
H28 H 0.489815 0.718456 0.736962 0.046 Uiso 1 1 calc R U . . .
C29 C 0.6023(2) 0.6533(2) 0.59795(14) 0.0333(5) Uani 1 1 d . . . . .
C30 C 0.5706(2) 0.5665(2) 0.62575(14) 0.0333(5) Uani 1 1 d . . . . .
H30 H 0.582149 0.504596 0.605423 0.040 Uiso 1 1 calc R U . . .
C31 C 0.6600(2) 0.6708(2) 0.53294(15) 0.0387(6) Uani 1 1 d . . . . .
C32 C 0.7328(5) 0.7913(4) 0.4579(3) 0.0825(14) Uani 1 1 d D U . . .
H32A H 0.725476 0.737974 0.421288 0.099 Uiso 0.65(3) 1 calc R U P B 1
H32B H 0.695979 0.849762 0.433243 0.099 Uiso 0.65(3) 1 calc R U P B 1
H32C H 0.768973 0.732895 0.439311 0.099 Uiso 0.35(3) 1 calc R U P B 2
H32D H 0.674783 0.816969 0.417268 0.099 Uiso 0.35(3) 1 calc R U P B 2
C33 C 0.8558(11) 0.8100(13) 0.4837(6) 0.082(4) Uani 0.65(3) 1 d D U P B 1
H33A H 0.862518 0.861802 0.520697 0.123 Uiso 0.65(3) 1 calc R U P B 1
H33B H 0.895195 0.829628 0.441719 0.123 Uiso 0.65(3) 1 calc R U P B 1
H33C H 0.892642 0.751115 0.505997 0.123 Uiso 0.65(3) 1 calc R U P B 1
C33A C 0.819(2) 0.861(2) 0.4779(11) 0.085(6) Uani 0.35(3) 1 d D U P B 2
H33D H 0.782392 0.923062 0.485524 0.127 Uiso 0.35(3) 1 calc R U P B 2
H33E H 0.868619 0.867010 0.438374 0.127 Uiso 0.35(3) 1 calc R U P B 2
H33F H 0.868108 0.840866 0.523890 0.127 Uiso 0.35(3) 1 calc R U P B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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
Cl1 C34 Cl2 100.9(5) . . ?
Cl1 C34 Cl3 102.0(7) . . ?
Cl1 C34 H34 116.0 . . ?
Cl2 C34 H34 116.0 . . ?
Cl3 C34 Cl2 103.5(4) . . ?
Cl3 C34 H34 116.0 . . ?
C9 O1 C11 118.1(3) . . ?
C31 O3 C32 116.6(3) . . ?
C13 N1 H1 125.6 . . ?
C14 N1 H1 125.6 . . ?
C14 N1 C13 108.79(19) . . ?
C28 N2 H2 125.5 . . ?
C28 N2 C29 109.0(2) . . ?
C29 N2 H2 125.5 . . ?
C2 C1 H1A 119.4 . . ?
C2 C1 C6 121.2(3) . . ?
C6 C1 H1A 119.4 . . ?
C1 C2 H2A 120.2 . . ?
C1 C2 C3 119.5(3) . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.1(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 117.7(3) . . ?
C4 C5 C10 122.4(2) . . ?
C10 C5 C6 119.9(3) . . ?
C1 C6 C5 119.4(3) . . ?
C7 C6 C1 122.1(3) . . ?
C7 C6 C5 118.4(3) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.6(3) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
O1 C9 C8 122.9(3) . . ?
O1 C9 C10 116.4(2) . . ?
C10 C9 C8 120.7(3) . . ?
C5 C10 C12 121.7(2) . . ?
C9 C10 C5 119.2(2) . . ?
C9 C10 C12 119.1(2) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C10 125.8(2) . . ?
C13 C12 C15 106.8(2) . . ?
C15 C12 C10 127.3(2) . . ?
N1 C13 C20 121.6(2) . . ?
C12 C13 N1 109.8(2) . . ?
C12 C13 C20 128.6(2) . . ?
N1 C14 C15 107.9(2) . . ?
N1 C14 C19 130.2(2) . . ?
C19 C14 C15 121.9(2) . . ?
C14 C15 C12 106.7(2) . . ?
C16 C15 C12 133.9(2) . . ?
C16 C15 C14 119.4(2) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 C15 118.6(2) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.4(2) . . ?
C19 C18 H18 119.3 . . ?
C14 C19 H19 121.2 . . ?
C18 C19 C14 117.6(2) . . ?
C18 C19 H19 121.2 . . ?
C13 C20 H20 107.2 . . ?
C13 C20 C21 111.8(2) . . ?
C21 C20 H20 107.2 . . ?
C27 C20 C13 112.68(19) . . ?
C27 C20 H20 107.2 . . ?
C27 C20 C21 110.59(19) . . ?
C22 C21 C20 118.8(2) . . ?
C26 C21 C20 122.7(2) . . ?
C26 C21 C22 118.5(2) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 C21 118.9(3) . . ?
C23 C22 H22 120.6 . . ?
F1 C23 C22 118.3(3) . . ?
C24 C23 F1 118.1(2) . . ?
C24 C23 C22 123.6(2) . . ?
C23 C24 H24 121.3 . . ?
C23 C24 C25 117.5(3) . . ?
C25 C24 H24 121.3 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.4(3) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 121.1(3) . . ?
C21 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C28 C27 C20 126.8(2) . . ?
C28 C27 C30 106.0(2) . . ?
C30 C27 C20 127.2(2) . . ?
N2 C28 C27 109.1(2) . . ?
N2 C28 H28 125.5 . . ?
C27 C28 H28 125.5 . . ?
N2 C29 C31 124.0(3) . . ?
C30 C29 N2 107.6(2) . . ?
C30 C29 C31 128.4(3) . . ?
C27 C30 H30 125.9 . . ?
C29 C30 C27 108.3(2) . . ?
C29 C30 H30 125.9 . . ?
O2 C31 O3 124.6(3) . . ?
O2 C31 C29 123.5(3) . . ?
O3 C31 C29 111.9(3) . . ?
O3 C32 H32A 109.8 . . ?
O3 C32 H32B 109.8 . . ?
O3 C32 H32C 109.4 . . ?
O3 C32 H32D 109.4 . . ?
H32A C32 H32B 108.2 . . ?
H32C C32 H32D 108.0 . . ?
C33 C32 O3 109.5(5) . . ?
C33 C32 H32A 109.8 . . ?
C33 C32 H32B 109.8 . . ?
C33A C32 O3 111.2(9) . . ?
C33A C32 H32C 109.4 . . ?
C33A C32 H32D 109.4 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C33A H33D 109.5 . . ?
C32 C33A H33E 109.5 . . ?
C32 C33A H33F 109.5 . . ?
H33D C33A H33E 109.5 . . ?
H33D C33A H33F 109.5 . . ?
H33E C33A H33F 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
Cl1 C34 1.737(9) . ?
Cl2 C34 1.806(9) . ?
Cl3 C34 1.804(9) . ?
C34 H34 1.0000 . ?
F1 C23 1.365(3) . ?
O1 C9 1.364(4) . ?
O1 C11 1.433(4) . ?
O2 C31 1.215(4) . ?
O3 C31 1.337(4) . ?
O3 C32 1.460(4) . ?
N1 H1 0.8800 . ?
N1 C13 1.377(3) . ?
N1 C14 1.370(3) . ?
N2 H2 0.8800 . ?
N2 C28 1.354(4) . ?
N2 C29 1.372(4) . ?
C1 H1A 0.9500 . ?
C1 C2 1.357(6) . ?
C1 C6 1.417(5) . ?
C2 H2A 0.9500 . ?
C2 C3 1.407(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.367(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.413(4) . ?
C5 C6 1.427(3) . ?
C5 C10 1.419(4) . ?
C6 C7 1.413(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.356(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.416(4) . ?
C9 C10 1.388(4) . ?
C10 C12 1.482(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.367(3) . ?
C12 C15 1.433(3) . ?
C13 C20 1.517(3) . ?
C14 C15 1.412(3) . ?
C14 C19 1.397(3) . ?
C15 C16 1.405(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.400(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(4) . ?
C19 H19 0.9500 . ?
C20 H20 1.0000 . ?
C20 C21 1.531(4) . ?
C20 C27 1.506(3) . ?
C21 C22 1.398(3) . ?
C21 C26 1.386(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.379(4) . ?
C23 C24 1.363(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.392(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.389(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.381(4) . ?
C27 C30 1.408(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.372(4) . ?
C29 C31 1.456(4) . ?
C30 H30 0.9500 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 H32C 0.9900 . ?
C32 H32D 0.9900 . ?
C32 C33 1.450(12) . ?
C32 C33A 1.395(17) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C33A H33D 0.9800 . ?
C33A H33E 0.9800 . ?
C33A H33F 0.9800 . ?
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 C23 C24 C25 179.4(3) . . . . ?
O1 C9 C10 C5 178.0(2) . . . . ?
O1 C9 C10 C12 -2.8(4) . . . . ?
N1 C13 C20 C21 -101.1(3) . . . . ?
N1 C13 C20 C27 24.2(3) . . . . ?
N1 C14 C15 C12 0.7(3) . . . . ?
N1 C14 C15 C16 178.6(2) . . . . ?
N1 C14 C19 C18 -177.0(3) . . . . ?
N2 C29 C30 C27 -0.6(3) . . . . ?
N2 C29 C31 O2 177.4(3) . . . . ?
N2 C29 C31 O3 -2.3(4) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C1 C6 C7 C8 -178.5(3) . . . . ?
C2 C1 C6 C5 1.0(5) . . . . ?
C2 C1 C6 C7 179.1(3) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C3 C4 C5 C10 -178.8(3) . . . . ?
C4 C5 C6 C1 -1.3(4) . . . . ?
C4 C5 C6 C7 -179.5(3) . . . . ?
C4 C5 C10 C9 -179.8(3) . . . . ?
C4 C5 C10 C12 1.0(4) . . . . ?
C5 C6 C7 C8 -0.3(5) . . . . ?
C5 C10 C12 C13 80.7(3) . . . . ?
C5 C10 C12 C15 -104.5(3) . . . . ?
C6 C1 C2 C3 -0.2(5) . . . . ?
C6 C5 C10 C9 0.7(4) . . . . ?
C6 C5 C10 C12 -178.5(2) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C7 C8 C9 O1 -178.2(3) . . . . ?
C7 C8 C9 C10 0.9(5) . . . . ?
C8 C9 C10 C5 -1.2(4) . . . . ?
C8 C9 C10 C12 178.1(2) . . . . ?
C9 C10 C12 C13 -98.5(3) . . . . ?
C9 C10 C12 C15 76.3(3) . . . . ?
C10 C5 C6 C1 178.3(2) . . . . ?
C10 C5 C6 C7 0.1(4) . . . . ?
C10 C12 C13 N1 175.5(2) . . . . ?
C10 C12 C13 C20 -2.5(4) . . . . ?
C10 C12 C15 C14 -175.9(2) . . . . ?
C10 C12 C15 C16 6.7(5) . . . . ?
C11 O1 C9 C8 -16.6(4) . . . . ?
C11 O1 C9 C10 164.3(3) . . . . ?
C12 C13 C20 C21 76.7(3) . . . . ?
C12 C13 C20 C27 -158.0(2) . . . . ?
C12 C15 C16 C17 175.6(3) . . . . ?
C13 N1 C14 C15 -0.9(3) . . . . ?
C13 N1 C14 C19 176.3(3) . . . . ?
C13 C12 C15 C14 -0.3(3) . . . . ?
C13 C12 C15 C16 -177.7(3) . . . . ?
C13 C20 C21 C22 -163.2(2) . . . . ?
C13 C20 C21 C26 18.4(3) . . . . ?
C13 C20 C27 C28 80.5(3) . . . . ?
C13 C20 C27 C30 -98.4(3) . . . . ?
C14 N1 C13 C12 0.7(3) . . . . ?
C14 N1 C13 C20 178.9(2) . . . . ?
C14 C15 C16 C17 -1.5(4) . . . . ?
C15 C12 C13 N1 -0.2(3) . . . . ?
C15 C12 C13 C20 -178.2(2) . . . . ?
C15 C14 C19 C18 -0.2(4) . . . . ?
C15 C16 C17 C18 1.0(5) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
C17 C18 C19 C14 -0.3(5) . . . . ?
C19 C14 C15 C12 -176.7(2) . . . . ?
C19 C14 C15 C16 1.1(4) . . . . ?
C20 C21 C22 C23 -178.4(2) . . . . ?
C20 C21 C26 C25 178.0(3) . . . . ?
C20 C27 C28 N2 -178.8(2) . . . . ?
C20 C27 C30 C29 179.3(2) . . . . ?
C21 C20 C27 C28 -153.6(3) . . . . ?
C21 C20 C27 C30 27.5(3) . . . . ?
C21 C22 C23 F1 -179.7(2) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
C22 C21 C26 C25 -0.4(4) . . . . ?
C22 C23 C24 C25 -1.0(5) . . . . ?
C23 C24 C25 C26 0.6(5) . . . . ?
C24 C25 C26 C21 0.0(5) . . . . ?
C26 C21 C22 C23 0.0(4) . . . . ?
C27 C20 C21 C22 70.4(3) . . . . ?
C27 C20 C21 C26 -108.0(3) . . . . ?
C28 N2 C29 C30 0.8(3) . . . . ?
C28 N2 C29 C31 -179.5(3) . . . . ?
C28 C27 C30 C29 0.2(3) . . . . ?
C29 N2 C28 C27 -0.7(3) . . . . ?
C30 C27 C28 N2 0.3(3) . . . . ?
C30 C29 C31 O2 -2.9(5) . . . . ?
C30 C29 C31 O3 177.4(3) . . . . ?
C31 O3 C32 C33 -96.6(9) . . . . ?
C31 O3 C32 C33A -132.1(15) . . . . ?
C31 C29 C30 C27 179.7(3) . . . . ?
C32 O3 C31 O2 -1.2(6) . . . . ?
C32 O3 C31 C29 178.5(4) . . . . ?
