Salts, solvates and hydrates of the multi-kinase inhibitor drug pazopanib with hydroxybenzoic acids
Rai, Sunil K.; Baidya, Debjani; Nangia, Ashwini K.; CrystEngComm 23 (2021) 5994–6011; doi:10.1039/D1CE00785H

data_7243297
_publ_section_title
;
 Salts, solvates and hydrates of the multi-kinase inhibitor drug pazopanib
 with hydroxybenzoic acids
;
_journal_issue                   35
_journal_name_full               CrystEngComm
_journal_page_first              5994
_journal_page_last               6011
_journal_paper_doi               10.1039/D1CE00785H
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety
'2(C34 H32 Eu N5 O11), C6 Co N6, 6(H2 O), N O3, C H4 O'
_chemical_formula_sum            'C75 H80 Co Eu2 N17 O32'
_chemical_formula_weight         2094.41
_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             2021-07-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-07 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.8000(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2652(2)
_cell_length_b                   20.5445(4)
_cell_length_c                   39.9674(8)
_cell_measurement_reflns_used    9872
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.60
_cell_measurement_theta_min      2.42
_cell_volume                     8369.6(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            124064
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.629
_diffrn_reflns_theta_max         66.629
_diffrn_reflns_theta_min         2.422
_exptl_absorpt_coefficient_mu    12.945
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4463
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1585 before and 0.0673 after correction.
The Ratio of minimum to maximum transmission is 0.5929.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish white'
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             4232
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         2.486
_refine_diff_density_min         -1.288
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1145
_refine_ls_number_reflns         14751
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+51.8948P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1372
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11008
_reflns_number_total             14751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00785h2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7243295--7243297.cif.'
_cod_database_code               7243297
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.182
_shelx_estimated_absorpt_t_min   0.140
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H,H,H) groups, All O(H,H,H,H,H,H,H,H,H,H,H,H,H,H,H,H,
  H,H,H,H,H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N11-O31 = N11-O30 = N11-O32
 1.2 with sigma of 0.01
 O31-O30
 2.2 with sigma of 0.02
 O31-O32
 2.2 with sigma of 0.02
 O30-O32
 2.2 with sigma of 0.02
 O24-H24B
 0.85 with sigma of 0.01
3. Rigid bond restraints
 O31, N11, O30, O32
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(O30) \\sim Ueq, Uanis(O32) \\sim Ueq, Uanis(N11) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(O33) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Riding coordinates:
 O32(H17A,H11A,H9A,H10A,H17B,H19A,H18A,H18B,H12A,H9B,H10B,H19B,H11B,H16A,H16B,
 H12B,H23A,H25A,H25B,H27A,H27B,H24A,H28A,H28B,H29A,H29B), O33(H33A,H33B,H24B)
5.b Aromatic/amide H refined with riding coordinates:
 C42(H42), C43(H43), C55(H55), C54(H54), C60(H60), C45(H45), C46(H46),
 C68(H68), C66(H66), C8(H8), C65(H65), C63(H63), C57(H57), C12(H12), C9(H9),
 C21(H21), C40(H40), C62(H62), C67(H67), C34(H34), C23(H23), C26(H26), C25(H25),
  C11(H11), C58(H58), C59(H59), C20(H20), C6(H6), C37(H37), C24(H24), C14(H14),
 C38(H38), C33(H33), C3(H3), C29(H29), C4(H4), C28(H28), C41(H41), C7(H7),
 C31(H31), C51(H51), C48(H48), C50(H50), C32(H32), C15(H15), C49(H49), C17(H17),
  C16(H16)
5.c Idealised Me refined as rotating group:
 C75(H75A,H75B,H75C)
;
_shelx_res_checksum              86778
_shelx_hkl_checksum              49016
_olex2_submission_special_instructions 'No special instructions were received'