# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_vndb_ibp_0m
_database_code_depnum_ccdc_archive 'CCDC 2358466'
loop_
_audit_author_name
_audit_author_address
'Abishek K G'
;Institute of Chemical Technology, Mumbai, IndianOil campus, Bhubaneswar
India
;
_audit_update_record             
;
2024-05-27 deposited with the CCDC.	2025-04-16 downloaded from the CCDC.
;
_audit_creation_date             2023-12-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Vandetanib Ibuprofen'
_chemical_name_systematic        
'4-(((4-((4-bromo-2-fluorophenyl)amino)-6-methoxyquinazolin-7-yl)oxy)methyl)-1-methylpiperidin-1-ium 2-(4-isobutylphenyl)propanoate'
_chemical_formula_moiety         'C22 H25 Br F N4 O2, C13 H17 O2'
_chemical_formula_sum            'C35 H42 Br F N4 O4'
_chemical_formula_weight         681.63
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.192(3)
_cell_length_b                   13.023(4)
_cell_length_c                   13.452(4)
_cell_angle_alpha                94.774(8)
_cell_angle_beta                 105.146(8)
_cell_angle_gamma                94.739(7)
_cell_volume                     1707.2(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.252
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5802
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1201 before and 0.0815 after correction.
The Ratio of minimum to maximum transmission is 0.7782.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0946
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            54637
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.598
_diffrn_reflns_theta_min         2.248
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 quest photon detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   microfocus
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4753
_reflns_number_total             7898
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_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)'
_refine_diff_density_max         0.830
_refine_diff_density_min         -1.061
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         7898
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1242
_refine_ls_R_factor_gt           0.0728
_refine_ls_restrained_S_all      1.026
_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)+(0.0940P)²+1.9388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1808
_refine_ls_wR_factor_ref         0.2135
_refine_special_details          ?
_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
2. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C3) = Uanis(C2)
Uanis(C35) = Uanis(C1)
3.a Ternary CH refined with riding coordinates:
 N1(H1), C8(H8), C1(H1A), C32(H32)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C35(H35A,H35B)
3.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C13(H13), C16(H16), C19(H19), C23(H23), C24(H24), C25(H25), C27(H27),
 C28(H28), C30(H30), C31(H31)
3.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C18(H18A,H18B,H18C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C),
 C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br Br 0.15026(5) -0.43424(3) 0.09645(5) 0.0859(3) Uani 1 1 d . . . . .
F F 0.2736(4) -0.0715(2) -0.0003(2) 0.0869(9) Uani 1 1 d . . . . .
O1 O 0.6429(3) 0.4736(2) 0.1627(3) 0.0603(8) Uani 1 1 d . . . . .
O2 O 0.7792(3) 0.3196(2) 0.2052(2) 0.0553(7) Uani 1 1 d . . . . .
N1 N 0.8545(3) 0.8462(2) 0.1884(2) 0.0457(7) Uani 1 1 d . . . . .
H1 H 0.836213 0.866021 0.254983 0.055 Uiso 1 1 calc R U . . .
N2 N 0.2163(3) 0.2694(2) 0.1371(3) 0.0512(8) Uani 1 1 d . . . . .
N3 N 0.2171(3) 0.0868(2) 0.1519(3) 0.0497(8) Uani 1 1 d . . . . .
N4 N 0.4165(3) 0.0096(2) 0.1980(3) 0.0510(8) Uani 1 1 d . . . . .
H4 H 0.503237 0.017230 0.226497 0.061 Uiso 1 1 calc R U . . .
C00P C 0.2311(4) -0.2959(3) 0.1303(4) 0.0517(10) Uani 1 1 d . . . . .
C5 C 0.9528(5) 0.9301(4) 0.1710(4) 0.0702(13) Uani 1 1 d . . . . .
H5A H 0.969959 0.914168 0.104891 0.105 Uiso 1 1 calc R U . . .
H5B H 1.037068 0.934978 0.224657 0.105 Uiso 1 1 calc R U . . .
H5C H 0.914509 0.994931 0.172398 0.105 Uiso 1 1 calc R U . . .
C6 C 0.7225(4) 0.8367(3) 0.1074(3) 0.0478(9) Uani 1 1 d . . . . .
H6A H 0.738472 0.821703 0.039952 0.057 Uiso 1 1 calc R U . . .
H6B H 0.683605 0.902176 0.108311 0.057 Uiso 1 1 calc R U . . .
C7 C 0.6224(4) 0.7523(3) 0.1238(3) 0.0496(9) Uani 1 1 d . . . . .
H7A H 0.540282 0.744902 0.066550 0.059 Uiso 1 1 calc R U . . .
H7B H 0.597111 0.771959 0.186841 0.059 Uiso 1 1 calc R U . . .
C8 C 0.6814(4) 0.6483(3) 0.1317(3) 0.0464(9) Uani 1 1 d . . . . .
H8 H 0.700226 0.626958 0.065682 0.056 Uiso 1 1 calc R U . . .
C9 C 0.8164(4) 0.6620(3) 0.2165(3) 0.0527(10) Uani 1 1 d . . . . .
H9A H 0.799345 0.680529 0.282979 0.063 Uiso 1 1 calc R U . . .
H9B H 0.856719 0.597052 0.219485 0.063 Uiso 1 1 calc R U . . .
C10 C 0.9150(4) 0.7454(3) 0.1958(4) 0.0542(10) Uani 1 1 d . . . . .
H10A H 0.999062 0.753904 0.251354 0.065 Uiso 1 1 calc R U . . .
H10B H 0.936879 0.724748 0.131611 0.065 Uiso 1 1 calc R U . . .
C11 C 0.5778(4) 0.5670(3) 0.1498(4) 0.0575(11) Uani 1 1 d . . . . .
H11A H 0.550242 0.588898 0.211384 0.069 Uiso 1 1 calc R U . . .
H11B H 0.497274 0.555930 0.091138 0.069 Uiso 1 1 calc R U . . .
C12 C 0.5655(4) 0.3854(3) 0.1691(3) 0.0465(9) Uani 1 1 d . . . . .
C13 C 0.4277(4) 0.3750(3) 0.1561(3) 0.0462(9) Uani 1 1 d . . . . .
H13 H 0.379806 0.432680 0.145356 0.055 Uiso 1 1 calc R U . . .
C14 C 0.3572(4) 0.2784(3) 0.1587(3) 0.0421(8) Uani 1 1 d . . . . .
C15 C 0.4312(4) 0.1927(3) 0.1781(3) 0.0391(8) Uani 1 1 d . . . . .
C16 C 0.5754(4) 0.2045(3) 0.1940(3) 0.0420(8) Uani 1 1 d . . . . .
H16 H 0.624825 0.147891 0.207170 0.050 Uiso 1 1 calc R U . . .
C17 C 0.6410(4) 0.2988(3) 0.1899(3) 0.0425(8) Uani 1 1 d . . . . .
C18 C 0.8605(4) 0.2402(4) 0.2410(4) 0.0615(11) Uani 1 1 d . . . . .
H18A H 0.837509 0.181066 0.189745 0.092 Uiso 1 1 calc R U . . .
H18B H 0.843888 0.220863 0.304328 0.092 Uiso 1 1 calc R U . . .
H18C H 0.955367 0.264940 0.253273 0.092 Uiso 1 1 calc R U . . .
C19 C 0.1595(4) 0.1751(3) 0.1346(3) 0.0531(10) Uani 1 1 d . . . . .
H19 H 0.064539 0.168034 0.118247 0.064 Uiso 1 1 calc R U . . .
C20 C 0.3525(4) 0.0963(3) 0.1761(3) 0.0423(8) Uani 1 1 d . . . . .
C21 C 0.3488(4) -0.0913(3) 0.1765(3) 0.0443(8) Uani 1 1 d . . . . .
C22 C 0.2797(4) -0.1329(3) 0.0771(3) 0.0533(10) Uani 1 1 d . . . . .
C23 C 0.2205(5) -0.2326(3) 0.0522(3) 0.0597(11) Uani 1 1 d . . . . .
H23 H 0.173993 -0.257227 -0.015806 0.072 Uiso 1 1 calc R U . . .
C24 C 0.2990(4) -0.2587(3) 0.2306(3) 0.0543(10) Uani 1 1 d . . . . .
H24 H 0.306214 -0.301927 0.283075 0.065 Uiso 1 1 calc R U . . .
C25 C 0.3566(4) -0.1567(3) 0.2534(3) 0.0493(9) Uani 1 1 d . . . . .
H25 H 0.401398 -0.131528 0.321679 0.059 Uiso 1 1 calc R U . . .
O3 O 0.8337(3) 0.8988(3) 0.3767(2) 0.0719(9) Uani 1 1 d . . . . .
O4 O 0.6897(3) 0.9966(2) 0.2914(2) 0.0629(8) Uani 1 1 d . . . . .
C1 C 0.7438(10) 1.5267(5) 0.5556(7) 0.1317(15) Uani 1 1 d . . . . .
H1A H 0.657348 1.503376 0.570019 0.158 Uiso 1 1 calc R U . . .
C2 C 0.7428(10) 1.6395(5) 0.5339(7) 0.1317(15) Uani 1 1 d . . . . .
H2A H 0.819954 1.659532 0.508716 0.198 Uiso 1 1 calc R U . . .
H2B H 0.747985 1.682469 0.596662 0.198 Uiso 1 1 calc R U . . .
H2C H 0.659926 1.647565 0.482763 0.198 Uiso 1 1 calc R U . . .
C3 C 0.8627(9) 1.5221(5) 0.6532(7) 0.1317(15) Uani 1 1 d . . . . .
H3A H 0.873879 1.451003 0.664006 0.198 Uiso 1 1 calc R U . . .
H3B H 0.842531 1.556856 0.712363 0.198 Uiso 1 1 calc R U . . .
H3C H 0.945544 1.555448 0.643861 0.198 Uiso 1 1 calc R U . . .
C26 C 0.7546(6) 1.3438(4) 0.4824(4) 0.0695(13) Uani 1 1 d . . . . .
C27 C 0.6319(5) 1.2827(4) 0.4546(4) 0.0712(13) Uani 1 1 d . . . . .
H27 H 0.551805 1.314123 0.434712 0.085 Uiso 1 1 calc R U . . .
C28 C 0.6223(5) 1.1763(4) 0.4548(4) 0.0651(12) Uani 1 1 d . . . . .
H28 H 0.536247 1.138631 0.435139 0.078 Uiso 1 1 calc R U . . .
C29 C 0.7344(5) 1.1252(4) 0.4828(3) 0.0614(11) Uani 1 1 d . . . . .
C30 C 0.8585(6) 1.1834(4) 0.5151(4) 0.0736(15) Uani 1 1 d . . . . .
H30 H 0.937272 1.150936 0.537327 0.088 Uiso 1 1 calc R U . . .
C31 C 0.8690(6) 1.2917(5) 0.5154(4) 0.0815(15) Uani 1 1 d . . . . .
H31 H 0.954814 1.329497 0.538298 0.098 Uiso 1 1 calc R U . . .
C32 C 0.7182(7) 1.0061(4) 0.4732(4) 0.0839(17) Uani 1 1 d . . . . .
H32 H 0.619649 0.986775 0.459677 0.101 Uiso 1 1 calc R U . . .
C33 C 0.7522(4) 0.9661(3) 0.3729(3) 0.0500(9) Uani 1 1 d . . . . .
C34 C 0.7786(9) 0.9581(5) 0.5642(4) 0.106(2) Uani 1 1 d . . . . .
H34A H 0.753513 0.884569 0.551074 0.160 Uiso 1 1 calc R U . . .
H34B H 0.746346 0.985389 0.620888 0.160 Uiso 1 1 calc R U . . .
H34C H 0.876325 0.972294 0.581333 0.160 Uiso 1 1 calc R U . . .
C35 C 0.7623(10) 1.4584(5) 0.4714(7) 0.1317(15) Uani 1 1 d . . . . .
H35A H 0.850880 1.479726 0.461155 0.158 Uiso 1 1 calc R U . . .
H35B H 0.693652 1.468708 0.408915 0.158 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Br C00P 1.885(4) . ?
F C22 1.356(5) . ?
O1 C11 1.435(5) . ?
O1 C12 1.361(4) . ?
O2 C17 1.369(4) . ?
O2 C18 1.415(5) . ?
N1 H1 0.9800 . ?
N1 C5 1.495(5) . ?
N1 C6 1.481(5) . ?
N1 C10 1.495(5) . ?
N2 C14 1.382(5) . ?
N2 C19 1.307(5) . ?
N3 C19 1.344(5) . ?
N3 C20 1.326(5) . ?
N4 H4 0.8600 . ?
N4 C20 1.365(5) . ?
N4 C21 1.403(5) . ?
C00P C23 1.377(6) . ?
C00P C24 1.372(6) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.507(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.527(5) . ?
C8 H8 0.9800 . ?
C8 C9 1.526(5) . ?
C8 C11 1.512(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.511(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.362(5) . ?
C12 C17 1.423(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.404(5) . ?
C14 C15 1.403(5) . ?
C15 C16 1.422(5) . ?
C15 C20 1.427(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.361(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9300 . ?
C21 C22 1.379(6) . ?
C21 C25 1.384(5) . ?
C22 C23 1.362(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.384(5) . ?
C25 H25 0.9300 . ?
O3 C33 1.251(5) . ?
O4 C33 1.230(5) . ?
C1 H1A 0.9800 . ?
C1 C2 1.521(10) . ?
C1 C3 1.546(12) . ?
C1 C35 1.443(10) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C26 C27 1.370(7) . ?
C26 C31 1.388(8) . ?
C26 C35 1.510(8) . ?
C27 H27 0.9300 . ?
C27 C28 1.381(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.354(7) . ?
C29 C30 1.365(7) . ?
C29 C32 1.536(7) . ?
C30 H30 0.9300 . ?
C30 C31 1.405(8) . ?
C31 H31 0.9300 . ?
C32 H32 0.9800 . ?
C32 C33 1.539(6) . ?
C32 C34 1.437(8) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?

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
C12 O1 C11 118.0(3) . . ?
C17 O2 C18 116.8(3) . . ?
C5 N1 H1 107.5 . . ?
C6 N1 H1 107.5 . . ?
C6 N1 C5 111.1(3) . . ?
C6 N1 C10 111.8(3) . . ?
C10 N1 H1 107.5 . . ?
C10 N1 C5 111.2(3) . . ?
C19 N2 C14 114.5(3) . . ?
C20 N3 C19 115.4(3) . . ?
C20 N4 H4 118.2 . . ?
C20 N4 C21 123.6(3) . . ?
C21 N4 H4 118.2 . . ?
C23 C00P Br 118.6(3) . . ?
C24 C00P Br 120.9(3) . . ?
C24 C00P C23 120.5(4) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
N1 C6 C7 111.7(3) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C6 C7 C8 112.2(3) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C7 C8 H8 108.2 . . ?
C9 C8 C7 109.0(3) . . ?
C9 C8 H8 108.2 . . ?
C11 C8 C7 109.9(3) . . ?
C11 C8 H8 108.2 . . ?
C11 C8 C9 113.1(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 110.9(3) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
N1 C10 C9 110.8(3) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O1 C11 C8 106.8(3) . . ?
O1 C11 H11A 110.4 . . ?
O1 C11 H11B 110.4 . . ?
C8 C11 H11A 110.4 . . ?
C8 C11 H11B 110.4 . . ?
H11A C11 H11B 108.6 . . ?
O1 C12 C13 125.9(3) . . ?
O1 C12 C17 114.0(3) . . ?
C13 C12 C17 120.2(3) . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
N2 C14 C13 119.1(3) . . ?
N2 C14 C15 121.8(3) . . ?
C15 C14 C13 119.1(3) . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 C20 116.0(3) . . ?
C16 C15 C20 124.1(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.1 . . ?
O2 C17 C12 114.9(3) . . ?
C16 C17 O2 125.0(3) . . ?
C16 C17 C12 120.2(3) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 N3 130.1(4) . . ?
N2 C19 H19 115.0 . . ?
N3 C19 H19 115.0 . . ?
N3 C20 N4 117.8(3) . . ?
N3 C20 C15 122.2(3) . . ?
N4 C20 C15 120.0(3) . . ?
C22 C21 N4 121.9(3) . . ?
C22 C21 C25 116.6(3) . . ?
C25 C21 N4 121.3(3) . . ?
F C22 C21 117.9(4) . . ?
F C22 C23 118.4(4) . . ?
C23 C22 C21 123.7(4) . . ?
C00P C23 H23 120.8 . . ?
C22 C23 C00P 118.4(4) . . ?
C22 C23 H23 120.8 . . ?
C00P C24 H24 120.2 . . ?
C00P C24 C25 119.7(4) . . ?
C25 C24 H24 120.2 . . ?
C21 C25 H25 119.4 . . ?
C24 C25 C21 121.2(4) . . ?
C24 C25 H25 119.4 . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 C3 107.2(7) . . ?
C3 C1 H1A 109.0 . . ?
C35 C1 H1A 109.0 . . ?
C35 C1 C2 113.5(7) . . ?
C35 C1 C3 109.1(8) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C27 C26 C31 115.2(5) . . ?
C27 C26 C35 121.3(6) . . ?
C31 C26 C35 123.4(6) . . ?
C26 C27 H27 118.6 . . ?
C26 C27 C28 122.7(5) . . ?
C28 C27 H27 118.6 . . ?
C27 C28 H28 119.0 . . ?
C29 C28 C27 121.9(5) . . ?
C29 C28 H28 119.0 . . ?
C28 C29 C30 117.3(4) . . ?
C28 C29 C32 119.6(5) . . ?
C30 C29 C32 123.0(5) . . ?
C29 C30 H30 119.5 . . ?
C29 C30 C31 121.0(4) . . ?
C31 C30 H30 119.5 . . ?
C26 C31 C30 121.7(5) . . ?
C26 C31 H31 119.2 . . ?
C30 C31 H31 119.2 . . ?
C29 C32 H32 104.6 . . ?
C29 C32 C33 108.2(4) . . ?
C33 C32 H32 104.6 . . ?
C34 C32 C29 117.1(5) . . ?
C34 C32 H32 104.6 . . ?
C34 C32 C33 116.2(5) . . ?
O3 C33 C32 118.8(4) . . ?
O4 C33 O3 123.1(4) . . ?
O4 C33 C32 117.8(4) . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C1 C35 C26 117.4(7) . . ?
C1 C35 H35A 108.0 . . ?
C1 C35 H35B 108.0 . . ?
C26 C35 H35A 108.0 . . ?
C26 C35 H35B 108.0 . . ?
H35A C35 H35B 107.2 . . ?

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
Br C00P C23 C22 -179.6(3) . . . . ?
Br C00P C24 C25 -179.6(3) . . . . ?
F C22 C23 C00P 177.7(4) . . . . ?
O1 C12 C13 C14 176.4(4) . . . . ?
O1 C12 C17 O2 3.2(5) . . . . ?
O1 C12 C17 C16 -177.3(3) . . . . ?
N1 C6 C7 C8 -54.5(5) . . . . ?
N2 C14 C15 C16 176.4(3) . . . . ?
N2 C14 C15 C20 -1.1(5) . . . . ?
N4 C21 C22 F -2.9(6) . . . . ?
N4 C21 C22 C23 175.5(4) . . . . ?
N4 C21 C25 C24 -174.7(4) . . . . ?
C00P C24 C25 C21 -0.9(6) . . . . ?
C5 N1 C6 C7 179.9(3) . . . . ?
C5 N1 C10 C9 178.3(4) . . . . ?
C6 N1 C10 C9 -56.8(4) . . . . ?
C6 C7 C8 C9 54.6(5) . . . . ?
C6 C7 C8 C11 179.1(3) . . . . ?
C7 C8 C9 C10 -56.2(5) . . . . ?
C7 C8 C11 O1 -176.6(3) . . . . ?
C8 C9 C10 N1 57.9(5) . . . . ?
C9 C8 C11 O1 -54.4(5) . . . . ?
C10 N1 C6 C7 55.0(4) . . . . ?
C11 O1 C12 C13 5.6(6) . . . . ?
C11 O1 C12 C17 -175.3(4) . . . . ?
C11 C8 C9 C10 -178.8(3) . . . . ?
C12 O1 C11 C8 -173.1(3) . . . . ?
C12 C13 C14 N2 -175.0(4) . . . . ?
C12 C13 C14 C15 2.0(6) . . . . ?
C13 C12 C17 O2 -177.7(4) . . . . ?
C13 C12 C17 C16 1.9(6) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
C13 C14 C15 C20 -177.9(3) . . . . ?
C14 N2 C19 N3 1.7(7) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C14 C15 C20 N3 3.5(5) . . . . ?
C14 C15 C20 N4 -177.6(3) . . . . ?
C15 C16 C17 O2 179.1(3) . . . . ?
C15 C16 C17 C12 -0.4(6) . . . . ?
C16 C15 C20 N3 -173.8(4) . . . . ?
C16 C15 C20 N4 5.1(6) . . . . ?
C17 C12 C13 C14 -2.6(6) . . . . ?
C18 O2 C17 C12 171.0(4) . . . . ?
C18 O2 C17 C16 -8.6(6) . . . . ?
C19 N2 C14 C13 175.6(4) . . . . ?
C19 N2 C14 C15 -1.3(5) . . . . ?
C19 N3 C20 N4 177.8(4) . . . . ?
C19 N3 C20 C15 -3.3(5) . . . . ?
C20 N3 C19 N2 0.6(7) . . . . ?
C20 N4 C21 C22 60.3(6) . . . . ?
C20 N4 C21 C25 -124.5(4) . . . . ?
C20 C15 C16 C17 177.0(4) . . . . ?
C21 N4 C20 N3 13.2(6) . . . . ?
C21 N4 C20 C15 -165.7(3) . . . . ?
C21 C22 C23 C00P -0.7(7) . . . . ?
C22 C21 C25 C24 0.7(6) . . . . ?
C23 C00P C24 C25 0.3(6) . . . . ?
C24 C00P C23 C22 0.5(6) . . . . ?
C25 C21 C22 F -178.2(4) . . . . ?
C25 C21 C22 C23 0.1(6) . . . . ?
C2 C1 C35 C26 -175.7(8) . . . . ?
C3 C1 C35 C26 64.8(10) . . . . ?
C26 C27 C28 C29 0.0(8) . . . . ?
C27 C26 C31 C30 2.9(8) . . . . ?
C27 C26 C35 C1 85.8(10) . . . . ?
C27 C28 C29 C30 2.6(7) . . . . ?
C27 C28 C29 C32 -175.1(4) . . . . ?
C28 C29 C30 C31 -2.3(7) . . . . ?
C28 C29 C32 C33 99.8(6) . . . . ?
C28 C29 C32 C34 -126.6(6) . . . . ?
C29 C30 C31 C26 -0.4(8) . . . . ?
C29 C32 C33 O3 130.9(5) . . . . ?
C29 C32 C33 O4 -54.4(6) . . . . ?
C30 C29 C32 C33 -77.7(6) . . . . ?
C30 C29 C32 C34 55.9(8) . . . . ?
C31 C26 C27 C28 -2.7(8) . . . . ?
C31 C26 C35 C1 -97.8(9) . . . . ?
C32 C29 C30 C31 175.2(4) . . . . ?
C34 C32 C33 O3 -3.2(8) . . . . ?
C34 C32 C33 O4 171.6(6) . . . . ?
C35 C26 C27 C28 174.0(5) . . . . ?
C35 C26 C31 C30 -173.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vndb_mfa
_database_code_depnum_ccdc_archive 'CCDC 2358467'
loop_
_audit_author_name
_audit_author_address
'Abishek K G'
;Institute of Chemical Technology, Mumbai, IndianOil campus, Bhubaneswar
India
;
_audit_update_record             
;
2024-05-27 deposited with the CCDC.	2025-04-16 downloaded from the CCDC.
;
_audit_creation_date             2023-12-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Vandetanib Mefenamic acid'
_chemical_name_systematic        
'4-(((4-((4-bromo-2-fluorophenyl)amino)-6-methoxyquinazolin-7-yl)oxy)methyl)-1-methylpiperidin-1-ium 2-((2,3-dimethylphenyl)amino)benzoate'
_chemical_formula_moiety         'C22 H25 Br F N4 O2, C15 H14 N O2'
_chemical_formula_sum            'C37 H39 Br F N5 O4'
_chemical_formula_weight         716.64
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.7596(10)
_cell_length_b                   12.7738(10)
_cell_length_c                   13.1770(11)
_cell_angle_alpha                110.597(2)
_cell_angle_beta                 90.033(2)
_cell_angle_gamma                118.704(2)
_cell_volume                     1725.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7373
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      3.19
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.244
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6408
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1034 before and 0.0663 after correction.
The Ratio of minimum to maximum transmission is 0.8594.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33222
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         2.238
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 quest photon detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   microfocus
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5068
_reflns_number_total             7912
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_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)'
_refine_diff_density_max         0.770
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         7912
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0643
_refine_ls_restrained_S_all      1.009
_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)+(0.0542P)²+2.0660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1606
_refine_special_details          ?
_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
2.a Ternary CH refined with riding coordinates:
 N1(H1), C4(H4A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C9(H9), C12(H12), C15(H15), C19(H19), C21(H21), C22(H22), N5(H5),
 C25(H25), C26(H26), C27(H27), C32(H32), C33(H33), C34(H34), C35(H35)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br Br -0.25821(4) -0.61589(6) 0.97990(5) 0.0838(2) Uani 1 1 d . . . . .
F F 0.0700(2) -0.4968(2) 0.7460(2) 0.0667(6) Uani 1 1 d . . . . .
O1 O 0.4541(2) 0.1139(2) 0.56425(19) 0.0503(6) Uani 1 1 d . . . . .
O2 O 0.2309(2) -0.0481(3) 0.4764(2) 0.0560(7) Uani 1 1 d . . . . .
N1 N 0.7013(2) 0.4918(2) 0.4533(2) 0.0372(6) Uani 1 1 d . . . . .
H1 H 0.708560 0.560419 0.522048 0.045 Uiso 1 1 calc R U . . .
N2 N 0.4296(2) -0.0410(3) 0.8531(2) 0.0432(7) Uani 1 1 d . . . . .
N3 N 0.2356(2) -0.2111(3) 0.8580(2) 0.0409(6) Uani 1 1 d . . . . .
N4 N 0.0573(2) -0.2896(3) 0.7382(2) 0.0393(6) Uani 1 1 d . . . . .
H4 H 0.022231 -0.293955 0.679852 0.047 Uiso 1 1 calc R U . . .
C1 C 0.7370(4) 0.5483(4) 0.3696(3) 0.0594(10) Uani 1 1 d . . . . .
H1A H 0.820163 0.619364 0.394812 0.089 Uiso 1 1 calc R U . . .
H1B H 0.684654 0.579581 0.358897 0.089 Uiso 1 1 calc R U . . .
H1C H 0.729469 0.482730 0.300763 0.089 Uiso 1 1 calc R U . . .
C2 C 0.7851(3) 0.4491(3) 0.4775(3) 0.0399(7) Uani 1 1 d . . . . .
H2A H 0.867814 0.523313 0.505140 0.048 Uiso 1 1 calc R U . . .
H2B H 0.783964 0.385234 0.409637 0.048 Uiso 1 1 calc R U . . .
C3 C 0.7479(3) 0.3903(3) 0.5622(3) 0.0396(7) Uani 1 1 d . . . . .
H3A H 0.757381 0.456911 0.632400 0.048 Uiso 1 1 calc R U . . .
H3B H 0.801241 0.359318 0.573209 0.048 Uiso 1 1 calc R U . . .
C4 C 0.6160(3) 0.2777(3) 0.5257(3) 0.0357(7) Uani 1 1 d . . . . .
H4A H 0.608878 0.211542 0.455109 0.043 Uiso 1 1 calc R U . . .
C5 C 0.5342(3) 0.3272(3) 0.5050(3) 0.0395(7) Uani 1 1 d . . . . .
H5A H 0.449891 0.256075 0.479966 0.047 Uiso 1 1 calc R U . . .
H5B H 0.540207 0.393775 0.573499 0.047 Uiso 1 1 calc R U . . .
C6 C 0.5715(3) 0.3833(3) 0.4184(3) 0.0414(7) Uani 1 1 d . . . . .
H6A H 0.560861 0.315286 0.348785 0.050 Uiso 1 1 calc R U . . .
H6B H 0.519247 0.415314 0.406818 0.050 Uiso 1 1 calc R U . . .
C7 C 0.5787(3) 0.2150(3) 0.6077(3) 0.0444(8) Uani 1 1 d . . . . .
H7A H 0.628855 0.179240 0.615355 0.053 Uiso 1 1 calc R U . . .
H7B H 0.587539 0.278279 0.679790 0.053 Uiso 1 1 calc R U . . .
C8 C 0.3950(3) 0.0377(3) 0.6195(3) 0.0371(7) Uani 1 1 d . . . . .
C9 C 0.4467(3) 0.0417(3) 0.7125(3) 0.0375(7) Uani 1 1 d . . . . .
H9 H 0.529187 0.100876 0.743722 0.045 Uiso 1 1 calc R U . . .
C10 C 0.3743(3) -0.0444(3) 0.7613(2) 0.0335(6) Uani 1 1 d . . . . .
C11 C 0.2492(3) -0.1316(3) 0.7146(2) 0.0301(6) Uani 1 1 d . . . . .
C12 C 0.1979(3) -0.1360(3) 0.6166(2) 0.0322(6) Uani 1 1 d . . . . .
H12 H 0.115769 -0.195443 0.584065 0.039 Uiso 1 1 calc R U . . .
C13 C 0.2690(3) -0.0532(3) 0.5705(2) 0.0374(7) Uani 1 1 d . . . . .
C14 C 0.1058(4) -0.1334(5) 0.4243(4) 0.0741(13) Uani 1 1 d . . . . .
H14A H 0.091204 -0.122657 0.358140 0.111 Uiso 1 1 calc R U . . .
H14B H 0.056698 -0.113503 0.473864 0.111 Uiso 1 1 calc R U . . .
H14C H 0.084855 -0.221853 0.405436 0.111 Uiso 1 1 calc R U . . .
C15 C 0.3570(3) -0.1258(4) 0.8924(3) 0.0465(8) Uani 1 1 d . . . . .
H15 H 0.394423 -0.127169 0.952153 0.056 Uiso 1 1 calc R U . . .
C16 C 0.1816(3) -0.2112(3) 0.7719(2) 0.0327(6) Uani 1 1 d . . . . .
C17 C -0.0151(3) -0.3634(3) 0.7961(2) 0.0349(7) Uani 1 1 d . . . . .
C18 C -0.0073(3) -0.4659(3) 0.8006(3) 0.0419(8) Uani 1 1 d . . . . .
C19 C -0.0779(3) -0.5411(4) 0.8543(3) 0.0505(9) Uani 1 1 d . . . . .
H19 H -0.068906 -0.608143 0.857116 0.061 Uiso 1 1 calc R U . . .
C20 C -0.1622(3) -0.5150(3) 0.9038(3) 0.0447(8) Uani 1 1 d . . . . .
C21 C -0.1762(3) -0.4159(3) 0.8988(3) 0.0443(8) Uani 1 1 d . . . . .
H21 H -0.235211 -0.400525 0.930444 0.053 Uiso 1 1 calc R U . . .
C22 C -0.1016(3) -0.3400(3) 0.8464(3) 0.0413(7) Uani 1 1 d . . . . .
H22 H -0.109544 -0.271875 0.844864 0.050 Uiso 1 1 calc R U . . .
O3 O -0.0892(2) -0.2290(2) 0.6232(2) 0.0463(6) Uani 1 1 d . . . . .
O4 O -0.2870(2) -0.3156(2) 0.6193(2) 0.0540(6) Uani 1 1 d . . . . .
N5 N 0.0608(3) 0.0249(3) 0.7491(3) 0.0627(9) Uani 1 1 d . . . . .
H5 H 0.052044 -0.042245 0.694466 0.075 Uiso 1 1 calc R U . . .
C23 C 0.4173(5) 0.2745(6) 1.0610(4) 0.1002(18) Uani 1 1 d . . . . .
H23A H 0.370292 0.288609 1.115483 0.150 Uiso 1 1 calc R U . . .
H23B H 0.498488 0.349173 1.083981 0.150 Uiso 1 1 calc R U . . .
H23C H 0.421121 0.198887 1.053467 0.150 Uiso 1 1 calc R U . . .
C24 C 0.3590(4) 0.2541(4) 0.9534(3) 0.0578(10) Uani 1 1 d . . . . .
C25 C 0.4165(4) 0.3280(4) 0.8951(4) 0.0716(12) Uani 1 1 d . . . . .
H25 H 0.496498 0.396083 0.927107 0.086 Uiso 1 1 calc R U . . .
C26 C 0.3690(5) 0.3120(5) 0.7962(4) 0.0787(13) Uani 1 1 d . . . . .
H26 H 0.415015 0.366189 0.761484 0.094 Uiso 1 1 calc R U . . .
C27 C 0.2455(4) 0.2091(4) 0.7457(4) 0.0699(12) Uani 1 1 d . . . . .
H27 H 0.208044 0.194166 0.677442 0.084 Uiso 1 1 calc R U . . .
C28 C 0.1849(3) 0.1334(4) 0.8023(3) 0.0526(9) Uani 1 1 d . . . . .
C29 C 0.2338(4) 0.1489(4) 0.9026(3) 0.0558(9) Uani 1 1 d . . . . .
C30 C 0.1677(4) 0.0637(4) 0.9588(3) 0.0683(11) Uani 1 1 d . . . . .
H30A H 0.217202 0.034076 0.979907 0.103 Uiso 1 1 calc R U . . .
H30B H 0.093052 -0.010009 0.909680 0.103 Uiso 1 1 calc R U . . .
H30C H 0.149477 0.110842 1.023683 0.103 Uiso 1 1 calc R U . . .
C31 C -0.0434(3) 0.0218(3) 0.7798(3) 0.0423(8) Uani 1 1 d . . . . .
C32 C -0.0361(3) 0.1352(3) 0.8577(3) 0.0495(9) Uani 1 1 d . . . . .
H32 H 0.040125 0.209901 0.891985 0.059 Uiso 1 1 calc R U . . .
C33 C -0.1391(3) 0.1375(4) 0.8840(3) 0.0482(9) Uani 1 1 d . . . . .
H33 H -0.131585 0.212997 0.937082 0.058 Uiso 1 1 calc R U . . .
C34 C -0.2534(3) 0.0298(4) 0.8332(3) 0.0504(9) Uani 1 1 d . . . . .
H34 H -0.323131 0.033043 0.848793 0.061 Uiso 1 1 calc R U . . .
C35 C -0.2623(3) -0.0826(3) 0.7589(3) 0.0443(8) Uani 1 1 d . . . . .
H35 H -0.339506 -0.155847 0.725293 0.053 Uiso 1 1 calc R U . . .
C36 C -0.1602(3) -0.0916(3) 0.7315(2) 0.0344(7) Uani 1 1 d . . . . .
C37 C -0.1788(3) -0.2196(3) 0.6531(3) 0.0367(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Br C20 1.887(3) . ?
F C18 1.350(4) . ?
O1 C7 1.425(4) . ?
O1 C8 1.356(4) . ?
O2 C13 1.365(4) . ?
O2 C14 1.417(4) . ?
N1 H1 0.9800 . ?
N1 C1 1.480(4) . ?
N1 C2 1.491(4) . ?
N1 C6 1.491(4) . ?
N2 C10 1.377(4) . ?
N2 C15 1.316(4) . ?
N3 C15 1.350(4) . ?
N3 C16 1.326(4) . ?
N4 H4 0.8600 . ?
N4 C16 1.370(4) . ?
N4 C17 1.413(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.511(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.523(4) . ?
C4 H4A 0.9800 . ?
C4 C5 1.523(4) . ?
C4 C7 1.511(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.513(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.365(4) . ?
C8 C13 1.424(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.413(4) . ?
C10 C11 1.406(4) . ?
C11 C12 1.419(4) . ?
C11 C16 1.430(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.357(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9300 . ?
C17 C18 1.381(4) . ?
C17 C22 1.388(4) . ?
C18 C19 1.372(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.373(5) . ?
C20 C21 1.383(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.381(5) . ?
C22 H22 0.9300 . ?
O3 C37 1.256(4) . ?
O4 C37 1.264(4) . ?
N5 H5 0.8600 . ?
N5 C28 1.459(5) . ?
N5 C31 1.376(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23 C24 1.478(6) . ?
C24 C25 1.366(6) . ?
C24 C29 1.452(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.342(7) . ?
C26 H26 0.9300 . ?
C26 C27 1.431(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.371(6) . ?
C28 C29 1.367(5) . ?
C29 C30 1.460(6) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C32 1.409(5) . ?
C31 C36 1.414(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.371(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.375(5) . ?
C34 H34 0.9300 . ?
C34 C35 1.374(5) . ?
C35 H35 0.9300 . ?
C35 C36 1.398(4) . ?
C36 C37 1.496(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
C8 O1 C7 119.9(2) . . ?
C13 O2 C14 117.5(3) . . ?
C1 N1 H1 107.6 . . ?
C1 N1 C2 111.3(3) . . ?
C1 N1 C6 111.1(3) . . ?
C2 N1 H1 107.6 . . ?
C6 N1 H1 107.6 . . ?
C6 N1 C2 111.5(2) . . ?
C15 N2 C10 115.0(3) . . ?
C16 N3 C15 116.0(3) . . ?
C16 N4 H4 118.9 . . ?
C16 N4 C17 122.2(2) . . ?
C17 N4 H4 118.9 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
N1 C2 C3 111.2(2) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C2 C3 C4 111.6(3) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C3 C4 H4A 107.8 . . ?
C3 C4 C5 108.5(2) . . ?
C5 C4 H4A 107.8 . . ?
C7 C4 C3 112.2(3) . . ?
C7 C4 H4A 107.8 . . ?
C7 C4 C5 112.4(3) . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C4 110.4(3) . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
N1 C6 C5 111.1(3) . . ?
N1 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
O1 C7 C4 106.1(2) . . ?
O1 C7 H7A 110.5 . . ?
O1 C7 H7B 110.5 . . ?
C4 C7 H7A 110.5 . . ?
C4 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
O1 C8 C9 125.7(3) . . ?
O1 C8 C13 113.7(3) . . ?
C9 C8 C13 120.6(3) . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.7(3) . . ?
C10 C9 H9 120.1 . . ?
N2 C10 C9 118.5(3) . . ?
N2 C10 C11 121.9(3) . . ?
C11 C10 C9 119.6(3) . . ?
C10 C11 C12 119.7(3) . . ?
C10 C11 C16 116.0(2) . . ?
C12 C11 C16 124.3(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
O2 C13 C8 114.0(3) . . ?
C12 C13 O2 125.5(3) . . ?
C12 C13 C8 120.5(3) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 N3 128.9(3) . . ?
N2 C15 H15 115.6 . . ?
N3 C15 H15 115.6 . . ?
N3 C16 N4 118.4(3) . . ?
N3 C16 C11 121.9(3) . . ?
N4 C16 C11 119.7(3) . . ?
C18 C17 N4 121.7(3) . . ?
C18 C17 C22 117.0(3) . . ?
C22 C17 N4 121.3(3) . . ?
F C18 C17 118.4(3) . . ?
F C18 C19 118.4(3) . . ?
C19 C18 C17 123.1(3) . . ?
C18 C19 H19 120.8 . . ?
C18 C19 C20 118.4(3) . . ?
C20 C19 H19 120.8 . . ?
C19 C20 Br 118.9(3) . . ?
C19 C20 C21 120.7(3) . . ?
C21 C20 Br 120.4(2) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C17 C22 H22 119.4 . . ?
C21 C22 C17 121.3(3) . . ?
C21 C22 H22 119.4 . . ?
C28 N5 H5 117.5 . . ?
C31 N5 H5 117.5 . . ?
C31 N5 C28 124.9(3) . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
C25 C24 C23 124.0(4) . . ?
C25 C24 C29 116.0(4) . . ?
C29 C24 C23 120.1(4) . . ?
C24 C25 H25 116.8 . . ?
C26 C25 C24 126.5(5) . . ?
C26 C25 H25 116.8 . . ?
C25 C26 H26 121.0 . . ?
C25 C26 C27 118.0(5) . . ?
C27 C26 H26 121.0 . . ?
C26 C27 H27 121.5 . . ?
C28 C27 C26 117.0(4) . . ?
C28 C27 H27 121.5 . . ?
C27 C28 N5 117.3(4) . . ?
C29 C28 N5 117.7(4) . . ?
C29 C28 C27 124.9(4) . . ?
C24 C29 C30 119.0(4) . . ?
C28 C29 C24 117.6(4) . . ?
C28 C29 C30 123.4(4) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N5 C31 C32 120.0(3) . . ?
N5 C31 C36 121.8(3) . . ?
C32 C31 C36 118.2(3) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 C31 121.3(3) . . ?
C33 C32 H32 119.4 . . ?
C32 C33 H33 119.5 . . ?
C32 C33 C34 121.0(3) . . ?
C34 C33 H33 119.5 . . ?
C33 C34 H34 120.7 . . ?
C35 C34 C33 118.5(3) . . ?
C35 C34 H34 120.7 . . ?
C34 C35 H35 118.6 . . ?
C34 C35 C36 122.8(3) . . ?
C36 C35 H35 118.6 . . ?
C31 C36 C37 122.9(3) . . ?
C35 C36 C31 118.1(3) . . ?
C35 C36 C37 119.0(3) . . ?
O3 C37 O4 122.4(3) . . ?
O3 C37 C36 120.3(3) . . ?
O4 C37 C36 117.3(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
Br C20 C21 C22 177.5(2) . . . . ?
F C18 C19 C20 -175.9(3) . . . . ?
O1 C8 C9 C10 -179.5(3) . . . . ?
O1 C8 C13 O2 0.7(4) . . . . ?
O1 C8 C13 C12 -179.9(3) . . . . ?
N1 C2 C3 C4 55.9(3) . . . . ?
N2 C10 C11 C12 -176.7(3) . . . . ?
N2 C10 C11 C16 3.6(4) . . . . ?
N4 C17 C18 F -1.4(5) . . . . ?
N4 C17 C18 C19 -178.8(3) . . . . ?
N4 C17 C22 C21 177.1(3) . . . . ?
C1 N1 C2 C3 -179.5(3) . . . . ?
C1 N1 C6 C5 -178.9(3) . . . . ?
C2 N1 C6 C5 56.4(3) . . . . ?
C2 C3 C4 C5 -57.1(3) . . . . ?
C2 C3 C4 C7 178.1(3) . . . . ?
C3 C4 C5 C6 57.9(3) . . . . ?
C3 C4 C7 O1 179.0(3) . . . . ?
C4 C5 C6 N1 -58.4(3) . . . . ?
C5 C4 C7 O1 56.3(3) . . . . ?
C6 N1 C2 C3 -54.9(3) . . . . ?
C7 O1 C8 C9 -4.9(5) . . . . ?
C7 O1 C8 C13 176.0(3) . . . . ?
C7 C4 C5 C6 -177.3(3) . . . . ?
C8 O1 C7 C4 178.8(3) . . . . ?
C8 C9 C10 N2 178.0(3) . . . . ?
C8 C9 C10 C11 -1.2(5) . . . . ?
C9 C8 C13 O2 -178.4(3) . . . . ?
C9 C8 C13 C12 1.0(5) . . . . ?
C9 C10 C11 C12 2.5(4) . . . . ?
C9 C10 C11 C16 -177.3(3) . . . . ?
C10 N2 C15 N3 -3.0(5) . . . . ?
C10 C11 C12 C13 -2.0(4) . . . . ?
C10 C11 C16 N3 -5.9(4) . . . . ?
C10 C11 C16 N4 173.7(3) . . . . ?
C11 C12 C13 O2 179.6(3) . . . . ?
C11 C12 C13 C8 0.3(5) . . . . ?
C12 C11 C16 N3 174.4(3) . . . . ?
C12 C11 C16 N4 -6.1(4) . . . . ?
C13 C8 C9 C10 -0.5(5) . . . . ?
C14 O2 C13 C8 -178.5(3) . . . . ?
C14 O2 C13 C12 2.2(5) . . . . ?
C15 N2 C10 C9 -178.6(3) . . . . ?
C15 N2 C10 C11 0.5(4) . . . . ?
C15 N3 C16 N4 -175.7(3) . . . . ?
C15 N3 C16 C11 3.8(4) . . . . ?
C16 N3 C15 N2 0.9(6) . . . . ?
C16 N4 C17 C18 -66.9(4) . . . . ?
C16 N4 C17 C22 116.3(3) . . . . ?
C16 C11 C12 C13 177.7(3) . . . . ?
C17 N4 C16 N3 4.0(4) . . . . ?
C17 N4 C16 C11 -175.6(3) . . . . ?
C17 C18 C19 C20 1.5(5) . . . . ?
C18 C17 C22 C21 0.1(5) . . . . ?
C18 C19 C20 Br -179.1(3) . . . . ?
C18 C19 C20 C21 0.5(6) . . . . ?
C19 C20 C21 C22 -2.1(5) . . . . ?
C20 C21 C22 C17 1.8(5) . . . . ?
C22 C17 C18 F 175.6(3) . . . . ?
C22 C17 C18 C19 -1.8(5) . . . . ?
N5 C28 C29 C24 177.8(3) . . . . ?
N5 C28 C29 C30 -0.7(5) . . . . ?
N5 C31 C32 C33 175.4(4) . . . . ?
N5 C31 C36 C35 -173.5(3) . . . . ?
N5 C31 C36 C37 6.5(5) . . . . ?
C23 C24 C25 C26 178.4(5) . . . . ?
C23 C24 C29 C28 -179.2(4) . . . . ?
C23 C24 C29 C30 -0.6(6) . . . . ?
C24 C25 C26 C27 0.9(7) . . . . ?
C25 C24 C29 C28 -0.2(5) . . . . ?
C25 C24 C29 C30 178.4(4) . . . . ?
C25 C26 C27 C28 -0.5(7) . . . . ?
C26 C27 C28 N5 -177.5(4) . . . . ?
C26 C27 C28 C29 -0.2(6) . . . . ?
C27 C28 C29 C24 0.5(6) . . . . ?
C27 C28 C29 C30 -177.9(4) . . . . ?
C28 N5 C31 C32 9.1(6) . . . . ?
C28 N5 C31 C36 -173.7(3) . . . . ?
C29 C24 C25 C26 -0.5(7) . . . . ?
C31 N5 C28 C27 -106.4(5) . . . . ?
C31 N5 C28 C29 76.1(5) . . . . ?
C31 C32 C33 C34 -1.5(6) . . . . ?
C31 C36 C37 O3 -3.2(5) . . . . ?
C31 C36 C37 O4 176.7(3) . . . . ?
C32 C31 C36 C35 3.8(5) . . . . ?
C32 C31 C36 C37 -176.3(3) . . . . ?
C32 C33 C34 C35 3.0(5) . . . . ?
C33 C34 C35 C36 -1.0(5) . . . . ?
C34 C35 C36 C31 -2.4(5) . . . . ?
C34 C35 C36 C37 177.6(3) . . . . ?
C35 C36 C37 O3 176.8(3) . . . . ?
C35 C36 C37 O4 -3.3(4) . . . . ?
C36 C31 C32 C33 -1.9(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
