#------------------------------------------------------------------------------
#$Date: 2024-05-05 05:21:30 +0300 (Sun, 05 May 2024) $
#$Revision: 291600 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/83/7248300.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_7248300
loop_
_publ_author_name
'Zou, Yao'
'Meng, Xin'
'Zhang, Baoxi'
'Yu, Hongmei'
'He, Guorong'
'Gong, Ningbo'
'Lu, Yang'
'Du, Guanhua'
_publ_section_title
;
 Gefitinib salts/cocrystals with phenolic acids as a promising solid-state
 approach to improve solubility
;
_journal_issue                   15
_journal_name_full               CrystEngComm
_journal_page_first              2112
_journal_page_last               2122
_journal_paper_doi               10.1039/D4CE00039K
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C22 H25 Cl F N4 O3, C10 H9 O4'
_chemical_formula_sum            'C32 H34 Cl F N4 O7'
_chemical_formula_weight         641.08
_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   mixed
_audit_creation_date             2023-11-23
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-27 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.9370(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.83646(5)
_cell_length_b                   26.10472(10)
_cell_length_c                   10.91005(5)
_cell_measurement_reflns_used    5489
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.764
_cell_measurement_theta_min      3.386
_cell_volume                     3039.97(2)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Rigaku 002+'
_diffrn_measurement_method       /w/k
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            40367
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.764
_diffrn_reflns_theta_min         3.386
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.639
_exptl_absorpt_correction_T_max  0.808
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ' Higashi, T. (1995).  '
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.00045(7)
_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   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         5795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0363
_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)+(0.0536P)²+0.7565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1023
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5487
_reflns_number_total             5795
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00039k2.cif
_cod_data_source_block           6261
_cod_depositor_comments
'Adding full bibliography for 7248298--7248302.cif.'
_cod_original_cell_volume        3039.96(2)
_cod_database_code               7248300
_shelx_shelxl_version_number     2018/3
_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   0.808
_shelx_estimated_absorpt_t_min   0.745
_exptl_absorpt_special_details   sadabs
_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.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,
 H19B), C20(H20A,H20B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C4(H4A), C5(H5), C8(H8), C11(H11), C14(H14), C23(H23),
 C26(H26), C27(H27), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C32(H32A,H32B,H32C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4B)
;
_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
Cl1 Cl 0.37215(5) 0.61078(2) 0.84078(5) 0.07758(16) Uani 1 1 d . . . . .
F1 F 0.30300(10) 0.51384(5) 0.94994(10) 0.0768(3) Uani 1 1 d . . . . .
O1 O 1.02359(10) 0.45360(3) 0.24842(10) 0.0498(2) Uani 1 1 d . . . . .
O2 O 0.92120(10) 0.38608(3) 0.36431(10) 0.0485(2) Uani 1 1 d . . . . .
O3 O 1.00038(10) 0.10208(3) 0.43678(10) 0.0522(3) Uani 1 1 d . . . . .
N1 N 0.63137(10) 0.48613(4) 0.61915(11) 0.0416(2) Uani 1 1 d . . . . .
H1 H 0.649543 0.454390 0.610929 0.050 Uiso 1 1 calc R U . . .
N2 N 0.65872(12) 0.56897(4) 0.55194(12) 0.0505(3) Uani 1 1 d . . . . .
N3 N 0.79925(12) 0.58959(4) 0.41251(12) 0.0468(3) Uani 1 1 d . . . . .
N4 N 0.89189(10) 0.20191(4) 0.41843(10) 0.0350(2) Uani 1 1 d . . . . .
H4 H 0.825(2) 0.1996(8) 0.339(2) 0.081(6) Uiso 1 1 d . . . . .
C1 C 0.50595(14) 0.54459(6) 0.72794(14) 0.0482(3) Uani 1 1 d . . . . .
H1A H 0.531985 0.573216 0.688505 0.058 Uiso 1 1 calc R U . . .
C2 C 0.42418(14) 0.54989(6) 0.81165(14) 0.0522(4) Uani 1 1 d . . . . .
C3 C 0.38445(15) 0.50825(7) 0.87004(15) 0.0550(4) Uani 1 1 d . . . . .
C4 C 0.42728(16) 0.46016(7) 0.84776(15) 0.0577(4) Uani 1 1 d . . . . .
H4A H 0.401280 0.431844 0.888346 0.069 Uiso 1 1 calc R U . . .
C5 C 0.50897(14) 0.45411(6) 0.76497(14) 0.0508(3) Uani 1 1 d . . . . .
H5 H 0.537854 0.421532 0.750107 0.061 Uiso 1 1 calc R U . . .
C6 C 0.54885(12) 0.49601(5) 0.70332(12) 0.0410(3) Uani 1 1 d . . . . .
C7 C 0.68643(12) 0.51942(5) 0.54905(12) 0.0383(3) Uani 1 1 d . . . . .
C8 C 0.71702(16) 0.60039(5) 0.48329(16) 0.0545(4) Uani 1 1 d . . . . .
H8 H 0.695918 0.634834 0.486498 0.065 Uiso 1 1 calc R U . . .
C9 C 0.82771(12) 0.53828(5) 0.40595(12) 0.0383(3) Uani 1 1 d . . . . .
C10 C 0.77272(11) 0.50108(4) 0.47315(12) 0.0362(3) Uani 1 1 d . . . . .
C11 C 0.80454(12) 0.44898(5) 0.46158(12) 0.0390(3) Uani 1 1 d . . . . .
H11 H 0.769648 0.424138 0.506284 0.047 Uiso 1 1 calc R U . . .
C12 C 0.88609(12) 0.43487(4) 0.38531(12) 0.0390(3) Uani 1 1 d . . . . .
C13 C 0.94281(12) 0.47261(5) 0.31865(12) 0.0386(3) Uani 1 1 d . . . . .
C14 C 0.91330(13) 0.52314(5) 0.32939(12) 0.0405(3) Uani 1 1 d . . . . .
H14 H 0.950125 0.547755 0.285692 0.049 Uiso 1 1 calc R U . . .
C15 C 0.87372(14) 0.34679(5) 0.43372(14) 0.0456(3) Uani 1 1 d . . . . .
H15A H 0.783091 0.348766 0.422656 0.055 Uiso 1 1 calc R U . . .
H15B H 0.907414 0.350415 0.521609 0.055 Uiso 1 1 calc R U . . .
C16 C 0.91352(14) 0.29623(5) 0.38570(13) 0.0442(3) Uani 1 1 d . . . . .
H16A H 0.868230 0.290112 0.302256 0.053 Uiso 1 1 calc R U . . .
H16B H 1.002412 0.296915 0.382544 0.053 Uiso 1 1 calc R U . . .
C17 C 0.88580(14) 0.25408(5) 0.47175(12) 0.0417(3) Uani 1 1 d . . . . .
H17A H 0.945404 0.256203 0.548884 0.050 Uiso 1 1 calc R U . . .
H17B H 0.802787 0.259439 0.491362 0.050 Uiso 1 1 calc R U . . .
C18 C 0.86420(15) 0.16337(5) 0.51048(14) 0.0498(3) Uani 1 1 d . . . . .
H18A H 0.779317 0.168223 0.525476 0.060 Uiso 1 1 calc R U . . .
H18B H 0.920915 0.168297 0.588671 0.060 Uiso 1 1 calc R U . . .
C19 C 0.87844(15) 0.10961(5) 0.46394(16) 0.0529(4) Uani 1 1 d . . . . .
H19A H 0.863268 0.085191 0.526677 0.064 Uiso 1 1 calc R U . . .
H19B H 0.816905 0.103704 0.389514 0.064 Uiso 1 1 calc R U . . .
C20 C 1.02078(15) 0.13650(5) 0.34173(15) 0.0500(3) Uani 1 1 d . . . . .
H20A H 0.957613 0.130900 0.268403 0.060 Uiso 1 1 calc R U . . .
H20B H 1.102111 0.129730 0.319466 0.060 Uiso 1 1 calc R U . . .
C21 C 1.01547(12) 0.19159(5) 0.38280(13) 0.0405(3) Uani 1 1 d . . . . .
H21A H 1.081578 0.198001 0.453174 0.049 Uiso 1 1 calc R U . . .
H21B H 1.028001 0.214237 0.315539 0.049 Uiso 1 1 calc R U . . .
C22 C 1.08031(16) 0.48888(6) 0.17566(15) 0.0544(4) Uani 1 1 d . . . . .
H22A H 1.016427 0.506124 0.118513 0.082 Uiso 1 1 calc R U . . .
H22B H 1.134752 0.470737 0.130033 0.082 Uiso 1 1 calc R U . . .
H22C H 1.128010 0.513580 0.229351 0.082 Uiso 1 1 calc R U . . .
O4 O 0.16609(10) 0.30343(4) -0.36629(10) 0.0525(3) Uani 1 1 d . . . . .
H4B H 0.166980 0.334798 -0.369829 0.079 Uiso 1 1 calc R U . . .
O5 O 0.19555(14) 0.20349(4) -0.33276(13) 0.0812(5) Uani 1 1 d . . . . .
O6 O 0.70284(10) 0.12426(4) 0.17037(10) 0.0533(3) Uani 1 1 d . . . . .
O7 O 0.72782(11) 0.20698(4) 0.21894(11) 0.0603(3) Uani 1 1 d . . . . .
C23 C 0.36778(14) 0.21646(6) -0.16158(14) 0.0507(3) Uani 1 1 d . . . . .
H23 H 0.378980 0.181334 -0.150571 0.061 Uiso 1 1 calc R U . . .
C24 C 0.27576(14) 0.23435(6) -0.25544(14) 0.0495(3) Uani 1 1 d . . . . .
C25 C 0.25985(13) 0.28710(5) -0.27486(13) 0.0442(3) Uani 1 1 d . . . . .
C26 C 0.33770(15) 0.32016(6) -0.20032(17) 0.0581(4) Uani 1 1 d . . . . .
H26 H 0.329709 0.355250 -0.214153 0.070 Uiso 1 1 calc R U . . .
C27 C 0.42805(16) 0.30200(6) -0.10471(18) 0.0632(5) Uani 1 1 d . . . . .
H27 H 0.478707 0.325143 -0.054272 0.076 Uiso 1 1 calc R U . . .
C28 C 0.44419(13) 0.25006(6) -0.08303(14) 0.0493(3) Uani 1 1 d . . . . .
C29 C 0.53932(14) 0.23175(6) 0.01997(15) 0.0514(3) Uani 1 1 d . . . . .
H29 H 0.579015 0.256870 0.073100 0.062 Uiso 1 1 calc R U . . .
C30 C 0.57581(13) 0.18413(6) 0.04692(13) 0.0469(3) Uani 1 1 d . . . . .
H30 H 0.537216 0.157928 -0.003407 0.056 Uiso 1 1 calc R U . . .
C31 C 0.67520(13) 0.17023(5) 0.15332(13) 0.0430(3) Uani 1 1 d . . . . .
C32 C 0.2161(3) 0.14972(7) -0.3189(3) 0.1380(15) Uani 1 1 d . . . . .
H32A H 0.160374 0.131890 -0.382761 0.207 Uiso 1 1 calc R U . . .
H32B H 0.200687 0.139058 -0.238748 0.207 Uiso 1 1 calc R U . . .
H32C H 0.301254 0.142004 -0.325993 0.207 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'
Cl Cl 0.3639 0.7018 '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
C13 O1 C22 117.55(11) . . ?
C12 O2 C15 116.62(10) . . ?
C19 O3 C20 109.50(11) . . ?
C6 N1 H1 115.2 . . ?
C7 N1 H1 115.2 . . ?
C7 N1 C6 129.58(11) . . ?
C7 N2 C8 116.87(12) . . ?
C8 N3 C9 114.93(12) . . ?
C17 N4 H4 107.9(12) . . ?
C17 N4 C18 109.11(10) . . ?
C18 N4 H4 109.4(12) . . ?
C21 N4 H4 107.9(12) . . ?
C21 N4 C17 111.85(10) . . ?
C21 N4 C18 110.52(10) . . ?
C2 C1 H1A 120.3 . . ?
C2 C1 C6 119.40(14) . . ?
C6 C1 H1A 120.3 . . ?
C1 C2 Cl1 118.54(13) . . ?
C3 C2 Cl1 120.34(12) . . ?
C3 C2 C1 121.12(14) . . ?
F1 C3 C2 120.54(15) . . ?
F1 C3 C4 119.40(16) . . ?
C2 C3 C4 120.06(14) . . ?
C3 C4 H4A 120.2 . . ?
C3 C4 C5 119.68(15) . . ?
C5 C4 H4A 120.2 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.98(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 N1 124.17(13) . . ?
C5 C6 N1 117.09(12) . . ?
C5 C6 C1 118.74(13) . . ?
N1 C7 C10 120.26(11) . . ?
N2 C7 N1 119.01(12) . . ?
N2 C7 C10 120.72(12) . . ?
N2 C8 H8 115.3 . . ?
N3 C8 N2 129.32(13) . . ?
N3 C8 H8 115.3 . . ?
N3 C9 C10 121.59(12) . . ?
N3 C9 C14 118.66(12) . . ?
C14 C9 C10 119.75(11) . . ?
C9 C10 C7 116.53(11) . . ?
C9 C10 C11 119.00(12) . . ?
C11 C10 C7 124.47(12) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.49(12) . . ?
C12 C11 H11 119.8 . . ?
O2 C12 C11 125.79(12) . . ?
O2 C12 C13 113.80(11) . . ?
C11 C12 C13 120.41(11) . . ?
O1 C13 C12 114.43(11) . . ?
O1 C13 C14 125.87(12) . . ?
C14 C13 C12 119.69(12) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.63(12) . . ?
C13 C14 H14 119.7 . . ?
O2 C15 H15A 110.3 . . ?
O2 C15 H15B 110.3 . . ?
O2 C15 C16 107.11(11) . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 H15A 110.3 . . ?
C16 C15 H15B 110.3 . . ?
C15 C16 H16A 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
C17 C16 C15 108.77(11) . . ?
C17 C16 H16A 109.9 . . ?
C17 C16 H16B 109.9 . . ?
N4 C17 C16 113.40(10) . . ?
N4 C17 H17A 108.9 . . ?
N4 C17 H17B 108.9 . . ?
C16 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
N4 C18 C19 110.93(12) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
O3 C19 C18 110.64(12) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
O3 C20 H20A 109.3 . . ?
O3 C20 H20B 109.3 . . ?
O3 C20 C21 111.57(12) . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
N4 C21 C20 109.47(11) . . ?
N4 C21 H21A 109.8 . . ?
N4 C21 H21B 109.8 . . ?
C20 C21 H21A 109.8 . . ?
C20 C21 H21B 109.8 . . ?
H21A C21 H21B 108.2 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C25 O4 H4B 109.5 . . ?
C24 O5 C32 116.39(13) . . ?
C24 C23 H23 119.4 . . ?
C24 C23 C28 121.26(13) . . ?
C28 C23 H23 119.4 . . ?
O5 C24 C23 124.04(13) . . ?
O5 C24 C25 116.01(12) . . ?
C23 C24 C25 119.95(13) . . ?
O4 C25 C24 118.37(12) . . ?
O4 C25 C26 122.78(13) . . ?
C26 C25 C24 118.84(13) . . ?
C25 C26 H26 119.5 . . ?
C25 C26 C27 120.90(14) . . ?
C27 C26 H26 119.5 . . ?
C26 C27 H27 119.4 . . ?
C28 C27 C26 121.11(14) . . ?
C28 C27 H27 119.4 . . ?
C23 C28 C29 122.00(13) . . ?
C27 C28 C23 117.88(13) . . ?
C27 C28 C29 120.12(13) . . ?
C28 C29 H29 115.8 . . ?
C30 C29 C28 128.32(14) . . ?
C30 C29 H29 115.8 . . ?
C29 C30 H30 118.2 . . ?
C29 C30 C31 123.50(13) . . ?
C31 C30 H30 118.2 . . ?
O6 C31 O7 124.82(13) . . ?
O6 C31 C30 118.43(12) . . ?
O7 C31 C30 116.74(12) . . ?
O5 C32 H32A 109.5 . . ?
O5 C32 H32B 109.5 . . ?
O5 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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 C2 1.7342(15) . ?
F1 C3 1.3511(18) . ?
O1 C13 1.3531(16) . ?
O1 C22 1.4227(17) . ?
O2 C12 1.3600(14) . ?
O2 C15 1.4228(16) . ?
O3 C19 1.417(2) . ?
O3 C20 1.4181(18) . ?
N1 H1 0.8600 . ?
N1 C6 1.4116(17) . ?
N1 C7 1.3614(17) . ?
N2 C7 1.3296(16) . ?
N2 C8 1.340(2) . ?
N3 C8 1.307(2) . ?
N3 C9 1.3791(16) . ?
N4 H4 1.03(2) . ?
N4 C17 1.4869(15) . ?
N4 C18 1.4882(16) . ?
N4 C21 1.4822(17) . ?
C1 H1A 0.9300 . ?
C1 C2 1.385(2) . ?
C1 C6 1.3928(19) . ?
C2 C3 1.367(2) . ?
C3 C4 1.374(2) . ?
C4 H4A 0.9300 . ?
C4 C5 1.379(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(2) . ?
C7 C10 1.4341(18) . ?
C8 H8 0.9300 . ?
C9 C10 1.4094(18) . ?
C9 C14 1.4077(19) . ?
C10 C11 1.4141(17) . ?
C11 H11 0.9300 . ?
C11 C12 1.3648(19) . ?
C12 C13 1.4253(18) . ?
C13 C14 1.3673(17) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.5102(17) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.5097(18) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.509(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.5102(18) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O4 H4B 0.8200 . ?
O4 C25 1.3636(16) . ?
O5 C24 1.3650(17) . ?
O5 C32 1.425(2) . ?
O6 C31 1.2432(17) . ?
O7 C31 1.2716(17) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(2) . ?
C23 C28 1.394(2) . ?
C24 C25 1.399(2) . ?
C25 C26 1.372(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.385(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.382(2) . ?
C28 C29 1.468(2) . ?
C29 H29 0.9300 . ?
C29 C30 1.322(2) . ?
C30 H30 0.9300 . ?
C30 C31 1.4857(19) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
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
Cl1 C2 C3 F1 0.8(2) . . . . ?
Cl1 C2 C3 C4 -179.17(13) . . . . ?
F1 C3 C4 C5 179.06(14) . . . . ?
O1 C13 C14 C9 -179.85(12) . . . . ?
O2 C12 C13 O1 -1.39(17) . . . . ?
O2 C12 C13 C14 178.57(12) . . . . ?
O2 C15 C16 C17 169.79(12) . . . . ?
O3 C20 C21 N4 -58.27(15) . . . . ?
N1 C7 C10 C9 -178.50(11) . . . . ?
N1 C7 C10 C11 1.86(19) . . . . ?
N2 C7 C10 C9 1.66(18) . . . . ?
N2 C7 C10 C11 -177.98(13) . . . . ?
N3 C9 C10 C7 -0.37(18) . . . . ?
N3 C9 C10 C11 179.30(12) . . . . ?
N3 C9 C14 C13 -179.02(12) . . . . ?
N4 C18 C19 O3 56.92(17) . . . . ?
C1 C2 C3 F1 -178.88(14) . . . . ?
C1 C2 C3 C4 1.1(2) . . . . ?
C2 C1 C6 N1 179.47(12) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 N1 -179.28(13) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C6 N1 C7 N2 -3.1(2) . . . . ?
C6 N1 C7 C10 177.09(12) . . . . ?
C6 C1 C2 Cl1 179.98(11) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
C7 N1 C6 C1 1.3(2) . . . . ?
C7 N1 C6 C5 -178.54(13) . . . . ?
C7 N2 C8 N3 -0.3(3) . . . . ?
C7 C10 C11 C12 178.83(12) . . . . ?
C8 N2 C7 N1 178.76(13) . . . . ?
C8 N2 C7 C10 -1.4(2) . . . . ?
C8 N3 C9 C10 -1.1(2) . . . . ?
C8 N3 C9 C14 178.53(13) . . . . ?
C9 N3 C8 N2 1.5(3) . . . . ?
C9 C10 C11 C12 -0.80(19) . . . . ?
C10 C9 C14 C13 0.60(19) . . . . ?
C10 C11 C12 O2 -178.26(12) . . . . ?
C10 C11 C12 C13 1.6(2) . . . . ?
C11 C12 C13 O1 178.73(12) . . . . ?
C11 C12 C13 C14 -1.3(2) . . . . ?
C12 O2 C15 C16 174.22(12) . . . . ?
C12 C13 C14 C9 0.2(2) . . . . ?
C14 C9 C10 C7 -179.97(11) . . . . ?
C14 C9 C10 C11 -0.30(18) . . . . ?
C15 O2 C12 C11 -3.7(2) . . . . ?
C15 O2 C12 C13 176.38(12) . . . . ?
C15 C16 C17 N4 165.99(12) . . . . ?
C17 N4 C18 C19 -175.94(12) . . . . ?
C17 N4 C21 C20 174.26(11) . . . . ?
C18 N4 C17 C16 179.57(12) . . . . ?
C18 N4 C21 C20 52.48(15) . . . . ?
C19 O3 C20 C21 62.74(16) . . . . ?
C20 O3 C19 C18 -61.36(16) . . . . ?
C21 N4 C17 C16 56.98(15) . . . . ?
C21 N4 C18 C19 -52.55(16) . . . . ?
C22 O1 C13 C12 177.75(12) . . . . ?
C22 O1 C13 C14 -2.2(2) . . . . ?
O4 C25 C26 C27 176.97(16) . . . . ?
O5 C24 C25 O4 1.0(2) . . . . ?
O5 C24 C25 C26 -179.88(16) . . . . ?
C23 C24 C25 O4 -178.38(14) . . . . ?
C23 C24 C25 C26 0.7(2) . . . . ?
C23 C28 C29 C30 7.2(3) . . . . ?
C24 C23 C28 C27 -2.3(3) . . . . ?
C24 C23 C28 C29 177.73(15) . . . . ?
C24 C25 C26 C27 -2.1(3) . . . . ?
C25 C26 C27 C28 1.3(3) . . . . ?
C26 C27 C28 C23 0.9(3) . . . . ?
C26 C27 C28 C29 -179.11(17) . . . . ?
C27 C28 C29 C30 -172.84(18) . . . . ?
C28 C23 C24 O5 -177.89(17) . . . . ?
C28 C23 C24 C25 1.5(3) . . . . ?
C28 C29 C30 C31 178.99(15) . . . . ?
C29 C30 C31 O6 -179.77(15) . . . . ?
C29 C30 C31 O7 -1.3(2) . . . . ?
C32 O5 C24 C23 -4.5(3) . . . . ?
C32 O5 C24 C25 176.1(2) . . . . ?
