#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:40:59 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289455 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/79/7247907.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_7247907
loop_
_publ_author_name
'Bandaru, Ravi Kumar'
'Giri, Lopamudra'
'Krishna, Gamidi Rama'
'Dandela, Rambabu'
_publ_section_title
;
 Novel molecular adducts of an anti-cancer drug vandetanib with enhanced
 solubility
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              248
_journal_page_last               260
_journal_paper_doi               10.1039/D3CE01130E
_journal_volume                  26
_journal_year                    2024
_chemical_formula_sum            'C31 H42 Br F N4 O7'
_chemical_formula_weight         681.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-08-17 deposited with the CCDC.	2023-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                117.44(2)
_cell_angle_beta                 94.18(3)
_cell_angle_gamma                95.20(3)
_cell_formula_units_Z            2
_cell_length_a                   8.866(1)
_cell_length_b                   14.050(1)
_cell_length_c                   14.358(1)
_cell_measurement_reflns_used    51307
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.260
_cell_measurement_theta_min      2.653
_cell_volume                     1567.4(4)
_computing_cell_refinement       'APEX3 (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'PHOTON II CPAD'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            51307
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.260
_diffrn_reflns_theta_min         2.653
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.370
_exptl_absorpt_correction_T_max  0.825
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_refine_diff_density_max         1.086
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         11910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0384
_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)+(0.0437P)²+1.0445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9867
_reflns_number_total             11910
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce01130e2.cif
_cod_data_source_block           VAN-AzA
_cod_depositor_comments
'Adding full bibliography for 7247904--7247909.cif.'
_cod_original_cell_volume        1567.48(1)
_cod_database_code               7247907
_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_min   0.726
_shelx_estimated_absorpt_t_max   0.831
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.95578(2) -0.20776(2) 0.18493(2) 0.01967(4) Uani 1 1 d . . . . .
F1 F 0.75129(11) 0.01870(8) 0.53886(7) 0.02191(18) Uani 1 1 d . . . . .
N1 N 0.86692(13) 0.21807(9) 0.55994(9) 0.0147(2) Uani 1 1 d . . . . .
H1 H 0.947343 0.262194 0.597597 0.018 Uiso 1 1 calc R U . . .
N2 N 0.60524(13) 0.18096(10) 0.52155(10) 0.0162(2) Uani 1 1 d . . . . .
N3 N 0.43722(13) 0.29206(10) 0.63482(10) 0.0171(2) Uani 1 1 d . . . . .
N4 N 0.44648(14) 0.96744(10) 1.18560(10) 0.0164(2) Uani 1 1 d . . . . .
H4 H 0.369531 0.958713 1.128632 0.020 Uiso 1 1 calc R U . . .
O1 O 0.64912(12) 0.60674(8) 0.96215(8) 0.0187(2) Uani 1 1 d . . . . .
O2 O 0.92114(12) 0.56750(9) 0.93017(8) 0.0187(2) Uani 1 1 d . . . . .
O5 O 0.78013(18) 0.41896(11) 0.28707(11) 0.0344(3) Uani 1 1 d . . . . .
O6 O 0.74052(16) 0.25589(10) 0.27801(10) 0.0295(3) Uani 1 1 d . . . . .
H6 H 0.748873 0.235676 0.215407 0.044 Uiso 1 1 calc R U . . .
O3 O 1.19162(14) 0.95267(10) 1.07579(10) 0.0260(2) Uani 1 1 d . . . . .
O4 O 1.25443(15) 0.84372(11) 0.91891(10) 0.0292(3) Uani 1 1 d . . . . .
C1 C 0.88369(14) 0.12021(11) 0.47033(11) 0.0135(2) Uani 1 1 d . . . . .
C2 C 0.96730(16) 0.11975(11) 0.39164(12) 0.0166(2) Uani 1 1 d . . . . .
H2 H 1.008241 0.185305 0.396178 0.020 Uiso 1 1 calc R U . . .
C3 C 0.99094(16) 0.02296(11) 0.30610(11) 0.0165(2) Uani 1 1 d . . . . .
H3 H 1.047003 0.023604 0.254072 0.020 Uiso 1 1 calc R U . . .
C4 C 0.92895(15) -0.07419(11) 0.30044(11) 0.0151(2) Uani 1 1 d . . . . .
C5 C 0.84426(15) -0.07697(11) 0.37693(11) 0.0155(2) Uani 1 1 d . . . . .
H5 H 0.801737 -0.142448 0.371832 0.019 Uiso 1 1 calc R U . . .
C6 C 0.82509(15) 0.02038(11) 0.46073(11) 0.0149(2) Uani 1 1 d . . . . .
C7 C 0.72723(15) 0.24448(11) 0.58837(11) 0.0132(2) Uani 1 1 d . . . . .
C8 C 0.46777(15) 0.20907(12) 0.54905(12) 0.0175(3) Uani 1 1 d . . . . .
H8 H 0.383669 0.164142 0.501369 0.021 Uiso 1 1 calc R U . . .
C9 C 0.56215(15) 0.35810(11) 0.70497(11) 0.0142(2) Uani 1 1 d . . . . .
C10 C 0.71261(14) 0.33763(10) 0.68565(10) 0.0127(2) Uani 1 1 d . . . . .
C11 C 0.83744(15) 0.40749(11) 0.76137(11) 0.0138(2) Uani 1 1 d . . . . .
H11 H 0.936802 0.393745 0.749530 0.017 Uiso 1 1 calc R U . . .
C12 C 0.81173(15) 0.49533(11) 0.85207(11) 0.0143(2) Uani 1 1 d . . . . .
C13 C 0.65869(15) 0.51711(11) 0.87065(11) 0.0149(2) Uani 1 1 d . . . . .
C14 C 0.53708(15) 0.44891(11) 0.79857(11) 0.0161(2) Uani 1 1 d . . . . .
H14 H 0.437940 0.462536 0.811401 0.019 Uiso 1 1 calc R U . . .
C15 C 0.49992(16) 0.63542(12) 0.98580(12) 0.0181(3) Uani 1 1 d . . . . .
H15A H 0.442827 0.583028 1.000919 0.022 Uiso 1 1 calc R U . . .
H15B H 0.443651 0.637209 0.926234 0.022 Uiso 1 1 calc R U . . .
C16 C 0.52374(15) 0.74668(11) 1.08192(11) 0.0156(2) Uani 1 1 d . . . . .
H16 H 0.599047 0.746930 1.135529 0.019 Uiso 1 1 calc R U . . .
C17 C 0.58433(17) 0.83281(12) 1.05167(12) 0.0184(3) Uani 1 1 d . . . . .
H17A H 0.684730 0.819925 1.029875 0.022 Uiso 1 1 calc R U . . .
H17B H 0.517318 0.826102 0.991830 0.022 Uiso 1 1 calc R U . . .
C18 C 0.59524(16) 0.94724(12) 1.14208(12) 0.0192(3) Uani 1 1 d . . . . .
H18A H 0.674111 0.957922 1.197835 0.023 Uiso 1 1 calc R U . . .
H18B H 0.623852 0.998811 1.116933 0.023 Uiso 1 1 calc R U . . .
C19 C 0.39580(17) 0.88719(12) 1.22161(11) 0.0177(3) Uani 1 1 d . . . . .
H19A H 0.300271 0.902532 1.250775 0.021 Uiso 1 1 calc R U . . .
H19B H 0.471588 0.892469 1.276642 0.021 Uiso 1 1 calc R U . . .
C20 C 0.37451(16) 0.77369(11) 1.12873(11) 0.0160(2) Uani 1 1 d . . . . .
H20A H 0.296833 0.768288 1.074662 0.019 Uiso 1 1 calc R U . . .
H20B H 0.339836 0.721714 1.152117 0.019 Uiso 1 1 calc R U . . .
C21 C 0.45738(19) 1.07994(12) 1.27259(13) 0.0249(3) Uani 1 1 d . . . . .
H21A H 0.490170 1.129990 1.247450 0.037 Uiso 1 1 calc R U . . .
H21B H 0.359148 1.092844 1.296207 0.037 Uiso 1 1 calc R U . . .
H21C H 0.529888 1.089752 1.330395 0.037 Uiso 1 1 calc R U . . .
C22 C 1.07610(16) 0.55002(13) 0.91505(13) 0.0217(3) Uani 1 1 d . . . . .
H22A H 1.143454 0.605405 0.974638 0.033 Uiso 1 1 calc R U . . .
H22B H 1.090067 0.480368 0.908588 0.033 Uiso 1 1 calc R U . . .
H22C H 1.098654 0.552570 0.851790 0.033 Uiso 1 1 calc R U . . .
C23 C 0.75971(19) 0.36165(14) 0.32922(14) 0.0246(3) Uani 1 1 d . . . . .
C24 C 0.7565(2) 0.40587(14) 0.44730(14) 0.0289(3) Uani 1 1 d . . . . .
H24A H 0.675845 0.362265 0.458486 0.035 Uiso 1 1 calc R U . . .
H24B H 0.852595 0.398446 0.478548 0.035 Uiso 1 1 calc R U . . .
C25 C 0.7313(2) 0.52319(14) 0.50411(14) 0.0286(3) Uani 1 1 d . . . . .
H25A H 0.629392 0.529368 0.479950 0.034 Uiso 1 1 calc R U . . .
H25B H 0.803737 0.565854 0.485778 0.034 Uiso 1 1 calc R U . . .
C26 C 0.7495(2) 0.56947(14) 0.62423(13) 0.0260(3) Uani 1 1 d . . . . .
H26A H 0.681935 0.524188 0.642533 0.031 Uiso 1 1 calc R U . . .
H26B H 0.853581 0.568099 0.649151 0.031 Uiso 1 1 calc R U . . .
C27 C 0.7133(2) 0.68517(14) 0.67961(13) 0.0247(3) Uani 1 1 d . . . . .
H27A H 0.603885 0.683869 0.667644 0.030 Uiso 1 1 calc R U . . .
H27B H 0.761982 0.725736 0.647930 0.030 Uiso 1 1 calc R U . . .
C28 C 0.76570(18) 0.74430(13) 0.79917(12) 0.0227(3) Uani 1 1 d . . . . .
H28A H 0.718624 0.809841 0.831122 0.027 Uiso 1 1 calc R U . . .
H28B H 0.730699 0.698454 0.829404 0.027 Uiso 1 1 calc R U . . .
C29 C 0.93865(19) 0.77409(14) 0.82644(13) 0.0245(3) Uani 1 1 d . . . . .
H29A H 0.985604 0.708335 0.800500 0.029 Uiso 1 1 calc R U . . .
H29B H 0.975155 0.814486 0.791074 0.029 Uiso 1 1 calc R U . . .
C30 C 0.98632(19) 0.84102(14) 0.94395(13) 0.0244(3) Uani 1 1 d . . . . .
H30A H 0.953566 0.798032 0.977633 0.029 Uiso 1 1 calc R U . . .
H30B H 0.931567 0.903191 0.969553 0.029 Uiso 1 1 calc R U . . .
C31 C 1.15667(18) 0.88215(13) 0.98049(13) 0.0221(3) Uani 1 1 d . . . . .
O7W O 0.14684(12) 0.35808(10) 0.65140(10) 0.0211(2) Uani 1 1 d . . . . .
H7A H 0.162(3) 0.416(2) 0.6580(19) 0.032 Uiso 1 1 d . U . . .
H7B H 0.225(3) 0.336(2) 0.6452(19) 0.032 Uiso 1 1 d . U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C7 N1 C1 121.98(11) . . ?
C7 N1 H1 119.0 . . ?
C1 N1 H1 119.0 . . ?
C7 N2 C8 116.88(12) . . ?
C8 N3 C9 115.54(12) . . ?
C21 N4 C19 111.08(12) . . ?
C21 N4 C18 110.74(12) . . ?
C19 N4 C18 111.04(11) . . ?
C21 N4 H4 107.9 . . ?
C19 N4 H4 107.9 . . ?
C18 N4 H4 107.9 . . ?
C13 O1 C15 117.86(11) . . ?
C12 O2 C22 116.49(11) . . ?
C23 O6 H6 109.5 . . ?
C6 C1 C2 117.41(12) . . ?
C6 C1 N1 121.08(12) . . ?
C2 C1 N1 121.40(12) . . ?
C1 C2 C3 121.44(13) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 118.57(13) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C5 C4 C3 121.65(13) . . ?
C5 C4 Br1 118.19(11) . . ?
C3 C4 Br1 120.15(11) . . ?
C6 C5 C4 117.95(13) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
F1 C6 C5 118.51(12) . . ?
F1 C6 C1 118.47(12) . . ?
C5 C6 C1 122.98(13) . . ?
N2 C7 N1 117.26(12) . . ?
N2 C7 C10 121.48(12) . . ?
N1 C7 C10 121.26(12) . . ?
N3 C8 N2 128.26(13) . . ?
N3 C8 H8 115.9 . . ?
N2 C8 H8 115.9 . . ?
N3 C9 C10 121.88(12) . . ?
N3 C9 C14 118.33(12) . . ?
C10 C9 C14 119.80(12) . . ?
C9 C10 C11 119.60(12) . . ?
C9 C10 C7 115.97(12) . . ?
C11 C10 C7 124.43(12) . . ?
C12 C11 C10 120.09(12) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
O2 C12 C11 125.55(12) . . ?
O2 C12 C13 114.25(12) . . ?
C11 C12 C13 120.20(12) . . ?
O1 C13 C14 125.58(12) . . ?
O1 C13 C12 114.35(12) . . ?
C14 C13 C12 120.08(12) . . ?
C13 C14 C9 120.21(12) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
O1 C15 C16 106.70(11) . . ?
O1 C15 H15A 110.4 . . ?
C16 C15 H15A 110.4 . . ?
O1 C15 H15B 110.4 . . ?
C16 C15 H15B 110.4 . . ?
H15A C15 H15B 108.6 . . ?
C15 C16 C20 110.71(12) . . ?
C15 C16 C17 110.21(12) . . ?
C20 C16 C17 109.60(11) . . ?
C15 C16 H16 108.8 . . ?
C20 C16 H16 108.8 . . ?
C17 C16 H16 108.8 . . ?
C18 C17 C16 112.63(12) . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
N4 C18 C17 111.09(12) . . ?
N4 C18 H18A 109.4 . . ?
C17 C18 H18A 109.4 . . ?
N4 C18 H18B 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
N4 C19 C20 109.61(11) . . ?
N4 C19 H19A 109.7 . . ?
C20 C19 H19A 109.7 . . ?
N4 C19 H19B 109.7 . . ?
C20 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C19 C20 C16 110.95(12) . . ?
C19 C20 H20A 109.4 . . ?
C16 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
C16 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
N4 C21 H21A 109.5 . . ?
N4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 C23 O6 123.75(16) . . ?
O5 C23 C24 123.43(16) . . ?
O6 C23 C24 112.81(15) . . ?
C25 C24 C23 114.14(15) . . ?
C25 C24 H24A 108.7 . . ?
C23 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
C23 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C24 C25 C26 112.82(15) . . ?
C24 C25 H25A 109.0 . . ?
C26 C25 H25A 109.0 . . ?
C24 C25 H25B 109.0 . . ?
C26 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C27 C26 C25 112.05(14) . . ?
C27 C26 H26A 109.2 . . ?
C25 C26 H26A 109.2 . . ?
C27 C26 H26B 109.2 . . ?
C25 C26 H26B 109.2 . . ?
H26A C26 H26B 107.9 . . ?
C26 C27 C28 113.87(14) . . ?
C26 C27 H27A 108.8 . . ?
C28 C27 H27A 108.8 . . ?
C26 C27 H27B 108.8 . . ?
C28 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
C29 C28 C27 112.96(14) . . ?
C29 C28 H28A 109.0 . . ?
C27 C28 H28A 109.0 . . ?
C29 C28 H28B 109.0 . . ?
C27 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
C30 C29 C28 111.95(14) . . ?
C30 C29 H29A 109.2 . . ?
C28 C29 H29A 109.2 . . ?
C30 C29 H29B 109.2 . . ?
C28 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
C29 C30 C31 116.74(14) . . ?
C29 C30 H30A 108.1 . . ?
C31 C30 H30A 108.1 . . ?
C29 C30 H30B 108.1 . . ?
C31 C30 H30B 108.1 . . ?
H30A C30 H30B 107.3 . . ?
O4 C31 O3 122.99(15) . . ?
O4 C31 C30 121.07(14) . . ?
O3 C31 C30 115.88(15) . . ?
H7A O7W H7B 107(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.8971(13) . ?
F1 C6 1.3477(16) . ?
N1 C7 1.3624(17) . ?
N1 C1 1.4152(17) . ?
N1 H1 0.8600 . ?
N2 C7 1.3308(17) . ?
N2 C8 1.3458(17) . ?
N3 C8 1.3162(18) . ?
N3 C9 1.3753(18) . ?
N4 C21 1.4842(19) . ?
N4 C19 1.490(2) . ?
N4 C18 1.4952(19) . ?
N4 H4 0.9800 . ?
O1 C13 1.3528(16) . ?
O1 C15 1.4367(17) . ?
O2 C12 1.3570(17) . ?
O2 C22 1.4320(18) . ?
O5 C23 1.219(2) . ?
O6 C23 1.306(2) . ?
O6 H6 0.8200 . ?
O3 C31 1.258(2) . ?
O4 C31 1.258(2) . ?
C1 C6 1.3911(19) . ?
C1 C2 1.3938(19) . ?
C2 C3 1.3970(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(2) . ?
C5 C6 1.3793(19) . ?
C5 H5 0.9300 . ?
C7 C10 1.4329(18) . ?
C8 H8 0.9300 . ?
C9 C10 1.4105(18) . ?
C9 C14 1.4136(19) . ?
C10 C11 1.4192(18) . ?
C11 C12 1.3726(18) . ?
C11 H11 0.9300 . ?
C12 C13 1.4348(18) . ?
C13 C14 1.3738(19) . ?
C14 H14 0.9300 . ?
C15 C16 1.517(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C20 1.5272(19) . ?
C16 C17 1.530(2) . ?
C16 H16 0.9800 . ?
C17 C18 1.520(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.518(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.517(2) . ?
C24 C25 1.512(2) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.527(2) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.523(2) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.534(2) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.525(2) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.507(2) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.529(2) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
O7W H7A 0.78(3) . ?
O7W H7B 0.78(3) . ?
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
C7 N1 C1 C6 -57.72(19) . . . . ?
C7 N1 C1 C2 126.27(15) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
N1 C1 C2 C3 176.45(13) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C2 C3 C4 Br1 179.23(10) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
Br1 C4 C5 C6 -179.99(10) . . . . ?
C4 C5 C6 F1 -175.91(12) . . . . ?
C4 C5 C6 C1 1.5(2) . . . . ?
C2 C1 C6 F1 176.30(12) . . . . ?
N1 C1 C6 F1 0.14(19) . . . . ?
C2 C1 C6 C5 -1.1(2) . . . . ?
N1 C1 C6 C5 -177.26(12) . . . . ?
C8 N2 C7 N1 -178.47(13) . . . . ?
C8 N2 C7 C10 0.8(2) . . . . ?
C1 N1 C7 N2 -7.9(2) . . . . ?
C1 N1 C7 C10 172.85(13) . . . . ?
C9 N3 C8 N2 0.0(2) . . . . ?
C7 N2 C8 N3 -0.4(2) . . . . ?
C8 N3 C9 C10 0.0(2) . . . . ?
C8 N3 C9 C14 179.80(14) . . . . ?
N3 C9 C10 C11 -179.11(13) . . . . ?
C14 C9 C10 C11 1.1(2) . . . . ?
N3 C9 C10 C7 0.4(2) . . . . ?
C14 C9 C10 C7 -179.40(13) . . . . ?
N2 C7 C10 C9 -0.8(2) . . . . ?
N1 C7 C10 C9 178.40(12) . . . . ?
N2 C7 C10 C11 178.69(13) . . . . ?
N1 C7 C10 C11 -2.1(2) . . . . ?
C9 C10 C11 C12 -1.0(2) . . . . ?
C7 C10 C11 C12 179.54(13) . . . . ?
C22 O2 C12 C11 0.6(2) . . . . ?
C22 O2 C12 C13 -179.43(13) . . . . ?
C10 C11 C12 O2 179.78(13) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C15 O1 C13 C14 -1.5(2) . . . . ?
C15 O1 C13 C12 178.88(12) . . . . ?
O2 C12 C13 O1 0.88(18) . . . . ?
C11 C12 C13 O1 -179.17(13) . . . . ?
O2 C12 C13 C14 -178.74(13) . . . . ?
C11 C12 C13 C14 1.2(2) . . . . ?
O1 C13 C14 C9 179.33(14) . . . . ?
C12 C13 C14 C9 -1.1(2) . . . . ?
N3 C9 C14 C13 -179.86(13) . . . . ?
C10 C9 C14 C13 0.0(2) . . . . ?
C13 O1 C15 C16 -171.09(12) . . . . ?
O1 C15 C16 C20 -167.09(12) . . . . ?
O1 C15 C16 C17 71.49(14) . . . . ?
C15 C16 C17 C18 174.18(12) . . . . ?
C20 C16 C17 C18 52.10(16) . . . . ?
C21 N4 C18 C17 -179.02(13) . . . . ?
C19 N4 C18 C17 57.07(16) . . . . ?
C16 C17 C18 N4 -53.20(16) . . . . ?
C21 N4 C19 C20 175.79(11) . . . . ?
C18 N4 C19 C20 -60.50(14) . . . . ?
N4 C19 C20 C16 60.08(15) . . . . ?
C15 C16 C20 C19 -177.16(12) . . . . ?
C17 C16 C20 C19 -55.38(15) . . . . ?
O5 C23 C24 C25 18.1(3) . . . . ?
O6 C23 C24 C25 -162.80(16) . . . . ?
C23 C24 C25 C26 -172.46(16) . . . . ?
C24 C25 C26 C27 -176.17(16) . . . . ?
C25 C26 C27 C28 -166.24(15) . . . . ?
C26 C27 C28 C29 71.89(19) . . . . ?
C27 C28 C29 C30 174.72(14) . . . . ?
C28 C29 C30 C31 -176.11(14) . . . . ?
C29 C30 C31 O4 -14.5(2) . . . . ?
C29 C30 C31 O3 168.12(15) . . . . ?
