#------------------------------------------------------------------------------
#$Date: 2022-04-09 00:56:45 +0300 (Sat, 09 Apr 2022) $
#$Revision: 274432 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/99/7129940.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_7129940
loop_
_publ_author_name
'Mannava, M. K. Chaitanya'
'Bommaka, Manish K.'
'Dandela, Rambabu'
'Solomon, K. Anand'
'Nangia, Ashwini K.'
_publ_section_title
;
 Fluorobenzoic acid coformers to improve the solubility and permeability
 of the BCS class IV drug naftopidil
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC07187D
_journal_year                    2022
_chemical_formula_moiety         'C24 H29 N2 O3, C7 F3 O2'
_chemical_formula_sum            'C31 H29 F3 N2 O5'
_chemical_formula_weight         566.61
_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             2021-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-22 deposited with the CCDC.	2022-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.760(3)
_cell_length_b                   24.632(9)
_cell_length_c                   11.501(4)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.77
_cell_measurement_theta_min      2.31
_cell_volume                     2728.4(16)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1104
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            78146
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.118
_diffrn_reflns_theta_min         2.271
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6982
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1090 before and 0.0618 after correction.
The Ratio of minimum to maximum transmission is 0.9353.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       needle
_exptl_crystal_F_000             1184
_refine_diff_density_max         0.796
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         10332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0647
_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)+(0.0543P)²+2.2445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1694
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6221
_reflns_number_total             10332
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc07187d2.cif
_cod_data_source_block           mo_nfpd_245tfba_meoh_0m_a
_cod_database_code               7129940
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: F1(0.27125) F2(0.2) F6(0.73) F8(0.8)
3.a Ternary CH refined with riding coordinates:
 N2(H2), C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C18(H18A,H18B), C19(H19A,
 H19B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C13(H13), C14(H14), C16(H16), C17(H17), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24)
3.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
3.e Idealised tetrahedral OH refined as rotating group:
 O0AA(H0AA)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.90355(14) 0.10891(6) 0.56759(13) 0.0262(3) Uani 1 1 d . . . . .
O2 O 0.14008(13) -0.00503(5) -0.07145(12) 0.0203(3) Uani 1 1 d . . . . .
N1 N 0.37351(14) -0.06455(6) 0.04186(13) 0.0169(3) Uani 1 1 d . . . . .
N2 N 0.63001(14) -0.03082(6) 0.26050(13) 0.0174(3) Uani 1 1 d . . . . .
H2 H 0.6474 -0.0567 0.3307 0.021 Uiso 1 1 calc R . . . .
C1 C -0.0033(2) -0.13736(9) -0.22271(18) 0.0282(4) Uani 1 1 d . . . . .
H1 H -0.0870 -0.1532 -0.2794 0.034 Uiso 1 1 calc R . . . .
C2 C 0.00042(19) -0.08274(9) -0.18917(17) 0.0240(4) Uani 1 1 d . . . . .
H2A H -0.0805 -0.0622 -0.2242 0.029 Uiso 1 1 calc R . . . .
C3 C 0.12502(18) -0.05907(7) -0.10340(16) 0.0185(3) Uani 1 1 d . . . . .
C4 C 0.24788(17) -0.09059(7) -0.04542(15) 0.0177(3) Uani 1 1 d . . . . .
C5 C 0.37238(17) -0.04168(8) 0.15990(16) 0.0190(3) Uani 1 1 d . . . . .
H5A H 0.3794 -0.0708 0.2194 0.023 Uiso 1 1 calc R . . . .
H5B H 0.2858 -0.0226 0.1371 0.023 Uiso 1 1 calc R . . . .
C6 C 0.49328(18) -0.00290(8) 0.22495(16) 0.0195(3) Uani 1 1 d . . . . .
H6A H 0.4831 0.0271 0.1667 0.023 Uiso 1 1 calc R . . . .
H6B H 0.4923 0.0118 0.3028 0.023 Uiso 1 1 calc R . . . .
C7 C 0.74807(18) 0.00881(8) 0.30429(16) 0.0200(3) Uani 1 1 d . . . . .
H7A H 0.7255 0.0368 0.2386 0.024 Uiso 1 1 calc R . . . .
H7B H 0.8301 -0.0100 0.3107 0.024 Uiso 1 1 calc R . . . .
C8 C 0.78220(18) 0.03580(7) 0.43399(16) 0.0188(3) Uani 1 1 d . . . . .
H8 H 0.6984 0.0518 0.4330 0.023 Uiso 1 1 calc R . . . .
C9 C 0.88971(19) 0.07951(8) 0.45592(17) 0.0210(3) Uani 1 1 d . . . . .
H9A H 0.9777 0.0634 0.4706 0.025 Uiso 1 1 calc R . . . .
H9B H 0.8592 0.1033 0.3811 0.025 Uiso 1 1 calc R . . . .
C10 C 1.01846(19) 0.14034(7) 0.63226(17) 0.0195(3) Uani 1 1 d . . . . .
C11 C 1.01726(19) 0.16923(7) 0.74010(17) 0.0201(3) Uani 1 1 d . . . . .
C12 C 1.13107(19) 0.20361(7) 0.81471(16) 0.0201(3) Uani 1 1 d . . . . .
C13 C 1.1287(2) 0.23198(8) 0.92082(18) 0.0264(4) Uani 1 1 d . . . . .
H13 H 1.2017 0.2551 0.9698 0.032 Uiso 1 1 calc R . . . .
C14 C 1.0212(2) 0.22601(8) 0.9526(2) 0.0309(4) Uani 1 1 d . . . . .
H14 H 1.0221 0.2447 1.0233 0.037 Uiso 1 1 calc R . . . .
C15 C 0.0208(2) 0.02940(9) -0.13385(18) 0.0272(4) Uani 1 1 d . . . . .
H15A H -0.0102 0.0286 -0.2261 0.041 Uiso 1 1 calc GR . . . .
H15B H 0.0450 0.0659 -0.1027 0.041 Uiso 1 1 calc GR . . . .
H15C H -0.0523 0.0167 -0.1145 0.041 Uiso 1 1 calc GR . . . .
C16 C 0.1161(2) -0.16789(8) -0.17239(18) 0.0272(4) Uani 1 1 d . . . . .
H16 H 0.1140 -0.2039 -0.1975 0.033 Uiso 1 1 calc R . . . .
C17 C 0.2411(2) -0.14456(8) -0.08310(17) 0.0225(4) Uani 1 1 d . . . . .
H17 H 0.3213 -0.1656 -0.0483 0.027 Uiso 1 1 calc R . . . .
C18 C 0.50002(18) -0.09691(7) 0.08129(17) 0.0194(3) Uani 1 1 d . . . . .
H18A H 0.5001 -0.1144 0.0058 0.023 Uiso 1 1 calc R . . . .
H18B H 0.5027 -0.1250 0.1415 0.023 Uiso 1 1 calc R . . . .
C19 C 0.62622(18) -0.06097(7) 0.14524(16) 0.0183(3) Uani 1 1 d . . . . .
H19A H 0.7092 -0.0831 0.1731 0.022 Uiso 1 1 calc R . . . .
H19B H 0.6267 -0.0350 0.0821 0.022 Uiso 1 1 calc R . . . .
C20 C 1.12793(19) 0.14543(7) 0.60212(17) 0.0202(3) Uani 1 1 d . . . . .
H20 H 1.1278 0.1266 0.5320 0.024 Uiso 1 1 calc R . . . .
C21 C 1.24102(19) 0.17954(7) 0.67849(17) 0.0209(3) Uani 1 1 d . . . . .
H21 H 1.3156 0.1824 0.6586 0.025 Uiso 1 1 calc R . . . .
C22 C 1.24292(19) 0.20841(8) 0.78113(18) 0.0227(4) Uani 1 1 d . . . . .
H22 H 1.3174 0.2312 0.8289 0.027 Uiso 1 1 calc R . . . .
C23 C 0.9092(2) 0.19163(8) 0.8786(2) 0.0295(4) Uani 1 1 d . . . . .
H23 H 0.8363 0.1877 0.9004 0.035 Uiso 1 1 calc R . . . .
C24 C 0.9070(2) 0.16387(8) 0.77435(19) 0.0248(4) Uani 1 1 d . . . . .
H24 H 0.8324 0.1413 0.7258 0.030 Uiso 1 1 calc R . . . .
F1 F 0.4136(7) 0.1808(3) 0.0993(5) 0.0541(15) Uani 0.2712 1 d . . P . .
F2 F 0.5991(7) 0.1623(3) 0.6138(7) 0.0415(16) Uani 0.2 1 d . . P . .
F4 F 0.5914(2) 0.24259(7) 0.22348(19) 0.0640(5) Uani 1 1 d . . . . .
O5 O 0.34049(15) 0.04270(6) 0.39443(13) 0.0273(3) Uani 1 1 d . . . . .
F6 F 0.6952(2) 0.23532(7) 0.47977(18) 0.0416(5) Uani 0.73 1 d . . P . .
O7 O 0.39248(15) 0.09918(6) 0.56303(12) 0.0260(3) Uani 1 1 d . . . . .
F8 F 0.28557(15) 0.09799(7) 0.17200(13) 0.0307(3) Uani 0.8 1 d . . P . .
C25 C 0.5416(3) 0.20504(9) 0.2772(3) 0.0415(6) Uani 1 1 d . . . . .
C26 C 0.4374(3) 0.17105(9) 0.1984(2) 0.0362(5) Uani 1 1 d . . . . .
C27 C 0.3888(2) 0.13249(8) 0.25613(19) 0.0263(4) Uani 1 1 d . . . . .
C28 C 0.4382(2) 0.12827(8) 0.39047(19) 0.0240(4) Uani 1 1 d . . . . .
C29 C 0.38571(18) 0.08634(8) 0.45465(17) 0.0202(3) Uani 1 1 d . . . . .
C30 C 0.5960(3) 0.20173(9) 0.4110(3) 0.0409(6) Uani 1 1 d . . . . .
C31 C 0.5426(2) 0.16441(8) 0.4675(2) 0.0292(4) Uani 1 1 d . . . . .
O0AA O 0.84016(14) -0.00240(6) 0.53502(12) 0.0257(3) Uani 1 1 d . . . . .
H0AA H 0.7799 -0.0135 0.5543 0.039 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C10 O1 C9 119.04(14) . . ?
C3 O2 C15 117.85(15) . . ?
C4 N1 C5 115.17(13) . . ?
C4 N1 C18 115.56(14) . . ?
C18 N1 C5 108.12(13) . . ?
C6 N2 H2 109.0 . . ?
C7 N2 H2 109.0 . . ?
C7 N2 C6 111.87(14) . . ?
C7 N2 C19 107.65(13) . . ?
C19 N2 H2 109.0 . . ?
C19 N2 C6 110.30(13) . . ?
C2 C1 H1 119.8 . . ?
C16 C1 H1 119.8 . . ?
C16 C1 C2 120.33(18) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 C1 120.04(18) . . ?
C3 C2 H2A 120.0 . . ?
O2 C3 C2 123.98(17) . . ?
O2 C3 C4 115.58(15) . . ?
C2 C3 C4 120.42(18) . . ?
C3 C4 N1 118.49(16) . . ?
C17 C4 N1 123.41(16) . . ?
C17 C4 C3 117.98(16) . . ?
N1 C5 H5A 109.7 . . ?
N1 C5 H5B 109.7 . . ?
N1 C5 C6 109.74(14) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
N2 C6 C5 111.45(15) . . ?
N2 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N2 C7 H7A 108.7 . . ?
N2 C7 H7B 108.7 . . ?
N2 C7 C8 114.32(14) . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C7 C8 H8 110.2 . . ?
C9 C8 C7 107.82(14) . . ?
C9 C8 H8 110.2 . . ?
O0AA C8 C7 109.99(15) . . ?
O0AA C8 H8 110.2 . . ?
O0AA C8 C9 108.25(14) . . ?
O1 C9 C8 106.04(14) . . ?
O1 C9 H9A 110.5 . . ?
O1 C9 H9B 110.5 . . ?
C8 C9 H9A 110.5 . . ?
C8 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
O1 C10 C11 113.41(15) . . ?
O1 C10 C20 125.78(16) . . ?
C20 C10 C11 120.80(16) . . ?
C12 C11 C10 118.71(16) . . ?
C24 C11 C10 121.79(17) . . ?
C24 C11 C12 119.50(16) . . ?
C11 C12 C22 119.43(16) . . ?
C13 C12 C11 118.24(17) . . ?
C13 C12 C22 122.33(17) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.29(19) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C23 120.04(18) . . ?
C23 C14 H14 120.0 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C16 H16 120.1 . . ?
C1 C16 C17 119.75(19) . . ?
C17 C16 H16 120.1 . . ?
C4 C17 C16 121.37(18) . . ?
C4 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
N1 C18 H18A 109.7 . . ?
N1 C18 H18B 109.7 . . ?
N1 C18 C19 109.98(15) . . ?
H18A C18 H18B 108.2 . . ?
C19 C18 H18A 109.7 . . ?
C19 C18 H18B 109.7 . . ?
N2 C19 C18 112.58(14) . . ?
N2 C19 H19A 109.1 . . ?
N2 C19 H19B 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C10 C20 H20 120.2 . . ?
C10 C20 C21 119.60(17) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.3 . . ?
C22 C21 C20 121.39(17) . . ?
C22 C21 H21 119.3 . . ?
C12 C22 H22 120.0 . . ?
C21 C22 C12 120.06(17) . . ?
C21 C22 H22 120.0 . . ?
C14 C23 H23 119.8 . . ?
C24 C23 C14 120.40(19) . . ?
C24 C23 H23 119.8 . . ?
C11 C24 H24 119.7 . . ?
C23 C24 C11 120.51(19) . . ?
C23 C24 H24 119.7 . . ?
F4 C25 C26 119.4(2) . . ?
F4 C25 C30 119.5(2) . . ?
C26 C25 C30 121.1(2) . . ?
F1 C26 C25 107.6(4) . . ?
F1 C26 C27 134.1(4) . . ?
C25 C26 C27 118.3(2) . . ?
F8 C27 C28 121.11(17) . . ?
C26 C27 F8 116.11(19) . . ?
C26 C27 C28 122.8(2) . . ?
C27 C28 C29 123.25(18) . . ?
C27 C28 C31 117.17(18) . . ?
C31 C28 C29 119.57(17) . . ?
O5 C29 O7 126.91(17) . . ?
O5 C29 C28 116.86(16) . . ?
O7 C29 C28 116.23(17) . . ?
F6 C30 C25 117.7(2) . . ?
F6 C30 C31 122.3(2) . . ?
C25 C30 C31 120.1(2) . . ?
C28 C31 F2 119.6(3) . . ?
C30 C31 F2 119.9(3) . . ?
C30 C31 C28 120.5(2) . . ?
C8 O0AA H0AA 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
O1 C9 1.423(2) . ?
O1 C10 1.364(2) . ?
O2 C3 1.371(2) . ?
O2 C15 1.436(2) . ?
N1 C4 1.427(2) . ?
N1 C5 1.475(2) . ?
N1 C18 1.464(2) . ?
N2 H2 0.9800 . ?
N2 C6 1.506(2) . ?
N2 C7 1.500(2) . ?
N2 C19 1.504(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.395(3) . ?
C1 C16 1.374(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.390(2) . ?
C3 C4 1.417(2) . ?
C4 C17 1.390(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.515(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.521(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.517(3) . ?
C8 O0AA 1.407(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.435(2) . ?
C10 C20 1.374(3) . ?
C11 C12 1.420(3) . ?
C11 C24 1.413(3) . ?
C12 C13 1.416(3) . ?
C12 C22 1.423(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.369(3) . ?
C14 H14 0.9300 . ?
C14 C23 1.407(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C17 1.401(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.509(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20 0.9300 . ?
C20 C21 1.416(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.371(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.371(3) . ?
C24 H24 0.9300 . ?
F1 C26 1.079(5) . ?
F2 C31 1.513(8) . ?
F4 C25 1.350(3) . ?
O5 C29 1.254(2) . ?
F6 C30 1.303(3) . ?
O7 C29 1.256(2) . ?
F8 C27 1.391(3) . ?
C25 C26 1.369(4) . ?
C25 C30 1.383(4) . ?
C26 C27 1.388(3) . ?
C27 C28 1.396(3) . ?
C28 C29 1.518(3) . ?
C28 C31 1.397(3) . ?
C30 C31 1.390(3) . ?
O0AA H0AA 0.8200 . ?
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 C10 C11 C12 -179.65(16) . . . . ?
O1 C10 C11 C24 1.0(3) . . . . ?
O1 C10 C20 C21 -179.75(17) . . . . ?
O2 C3 C4 N1 1.5(2) . . . . ?
O2 C3 C4 C17 -174.51(15) . . . . ?
N1 C4 C17 C16 -177.89(16) . . . . ?
N1 C5 C6 N2 -58.63(18) . . . . ?
N1 C18 C19 N2 57.13(18) . . . . ?
N2 C7 C8 C9 -172.78(15) . . . . ?
N2 C7 C8 O0AA 69.38(19) . . . . ?
C1 C2 C3 O2 175.70(16) . . . . ?
C1 C2 C3 C4 -2.5(3) . . . . ?
C1 C16 C17 C4 -1.1(3) . . . . ?
C2 C1 C16 C17 2.5(3) . . . . ?
C2 C3 C4 N1 179.88(15) . . . . ?
C2 C3 C4 C17 3.9(2) . . . . ?
C3 C4 C17 C16 -2.1(3) . . . . ?
C4 N1 C5 C6 -164.87(15) . . . . ?
C4 N1 C18 C19 166.16(14) . . . . ?
C5 N1 C4 C3 62.5(2) . . . . ?
C5 N1 C4 C17 -121.75(18) . . . . ?
C5 N1 C18 C19 -63.10(17) . . . . ?
C6 N2 C7 C8 68.69(18) . . . . ?
C6 N2 C19 C18 -50.13(19) . . . . ?
C7 N2 C6 C5 170.47(13) . . . . ?
C7 N2 C19 C18 -172.43(14) . . . . ?
C7 C8 C9 O1 171.64(14) . . . . ?
C9 O1 C10 C11 177.94(16) . . . . ?
C9 O1 C10 C20 -2.2(3) . . . . ?
C10 O1 C9 C8 161.74(15) . . . . ?
C10 C11 C12 C13 179.92(17) . . . . ?
C10 C11 C12 C22 -0.2(3) . . . . ?
C10 C11 C24 C23 179.45(18) . . . . ?
C10 C20 C21 C22 -1.0(3) . . . . ?
C11 C10 C20 C21 0.1(3) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
C11 C12 C22 C21 -0.7(3) . . . . ?
C12 C11 C24 C23 0.1(3) . . . . ?
C12 C13 C14 C23 -0.7(3) . . . . ?
C13 C12 C22 C21 179.17(17) . . . . ?
C13 C14 C23 C24 0.1(3) . . . . ?
C14 C23 C24 C11 0.2(3) . . . . ?
C15 O2 C3 C2 -2.2(2) . . . . ?
C15 O2 C3 C4 176.13(14) . . . . ?
C16 C1 C2 C3 -0.7(3) . . . . ?
C18 N1 C4 C3 -170.27(14) . . . . ?
C18 N1 C4 C17 5.5(2) . . . . ?
C18 N1 C5 C6 64.18(18) . . . . ?
C19 N2 C6 C5 50.68(18) . . . . ?
C19 N2 C7 C8 -169.98(14) . . . . ?
C20 C10 C11 C12 0.5(3) . . . . ?
C20 C10 C11 C24 -178.83(18) . . . . ?
C20 C21 C22 C12 1.3(3) . . . . ?
C22 C12 C13 C14 -178.86(19) . . . . ?
C24 C11 C12 C13 -0.7(3) . . . . ?
C24 C11 C12 C22 179.17(17) . . . . ?
F1 C26 C27 F8 -0.7(6) . . . . ?
F1 C26 C27 C28 180.0(5) . . . . ?
F4 C25 C26 F1 1.2(5) . . . . ?
F4 C25 C26 C27 179.4(2) . . . . ?
F4 C25 C30 F6 -0.6(4) . . . . ?
F4 C25 C30 C31 177.9(2) . . . . ?
F6 C30 C31 F2 0.6(4) . . . . ?
F6 C30 C31 C28 -178.6(2) . . . . ?
F8 C27 C28 C29 0.6(3) . . . . ?
F8 C27 C28 C31 179.63(18) . . . . ?
C25 C26 C27 F8 -178.31(19) . . . . ?
C25 C26 C27 C28 2.4(3) . . . . ?
C25 C30 C31 F2 -177.8(4) . . . . ?
C25 C30 C31 C28 3.0(3) . . . . ?
C26 C25 C30 F6 179.9(2) . . . . ?
C26 C25 C30 C31 -1.6(4) . . . . ?
C26 C27 C28 C29 179.87(18) . . . . ?
C26 C27 C28 C31 -1.1(3) . . . . ?
C27 C28 C29 O5 28.1(3) . . . . ?
C27 C28 C29 O7 -151.99(18) . . . . ?
C27 C28 C31 F2 179.2(3) . . . . ?
C27 C28 C31 C30 -1.6(3) . . . . ?
C29 C28 C31 F2 -1.7(4) . . . . ?
C29 C28 C31 C30 177.49(19) . . . . ?
C30 C25 C26 F1 -179.2(4) . . . . ?
C30 C25 C26 C27 -1.0(3) . . . . ?
C31 C28 C29 O5 -150.92(18) . . . . ?
C31 C28 C29 O7 29.0(3) . . . . ?
O0AA C8 C9 O1 -69.40(18) . . . . ?
