Cocrystallization of multi-kinase inhibitor pazopanib with fenamic acids: improving dissolution and inhibiting cell migration
Rai, Sunil K.; Gunnam, Anilkumar; Roy, Debopriya; Rajput, Raveena; Kulkarni, Kiran; Nangia, Ashwini K.; CrystEngComm 25 (2023) 5565–5574; doi:10.1039/D3CE00773A

data_7247328
_publ_section_title
;
 Cocrystallization of multi-kinase inhibitor pazopanib with fenamic acids:
 improving dissolution and inhibiting cell migration
;
_journal_issue                   39
_journal_name_full               CrystEngComm
_journal_page_first              5565
_journal_page_last               5574
_journal_paper_doi               10.1039/D3CE00773A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C21 H24 N7 O2 S, C14 H9 F3 N O2, C2 H3 N'
_chemical_formula_sum            'C37 H36 F3 N9 O4 S'
_chemical_formula_weight         759.81
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-02-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-01-26 deposited with the CCDC.	2023-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                68.40(4)
_cell_angle_beta                 89.70(4)
_cell_angle_gamma                81.04(4)
_cell_formula_units_Z            4
_cell_length_a                   10.125(11)
_cell_length_b                   18.32(2)
_cell_length_c                   20.77(2)
_cell_measurement_reflns_used    9660
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.52
_cell_measurement_theta_min      2.43
_cell_volume                     3533(7)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            137425
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.445
_diffrn_reflns_theta_min         2.243
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1378 before and 0.0975 after correction.
The Ratio of minimum to maximum transmission is 0.8748.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            silver
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       ROD
_exptl_crystal_F_000             1584
_refine_diff_density_max         3.163
_refine_diff_density_min         -0.722
_refine_diff_density_rms         0.176
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.568
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1009
_refine_ls_number_reflns         14400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.568
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.1099
_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/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3240
_refine_ls_wR_factor_ref         0.3363
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13131
_reflns_number_total             14400
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00773a2.cif
_cod_data_source_block           mo_paz_ffa_b_0m_a
_cod_depositor_comments
'Adding full bibliography for 7247326--7247328.cif.'
_cod_original_cell_volume        3533(6)
_cod_database_code               7247328
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.938
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9146(12)
 0.0854(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N15(H15), C49(H49), C57(H57), C43(H43), C56(H56), C46(H46), C45(H45), N5(H5),
 N6(H6), C20(H20), C6(H6A), C13(H13), C12(H12), C19(H19), C8(H8), C9(H9),
 N8(H8A), C24(H24), C25(H25), C27(H27), C26(H26), C34(H34), C30(H30), C32(H32),
 C31(H31), N17(H17), C61(H61), C63(H63), C62(H62), C71(H71), C64(H64), C67(H67),
  C68(H68), C69(H69), C36(H36)
3.b Idealised Me refined as rotating group:
 C47(H47A,H47B,H47C), C38(H38A,H38B,H38C), C58(H58A,H58B,H58C), C39(H39A,H39B,
 H39C), C10(H10A,H10B,H10C), C21(H21A,H21B,H21C), C1(H1A,H1B,H1C), C2(H2A,H2B,
 H2C), C73(H73A,H73B,H73C), C74(H74A,H74B,H74C)
;
_shelx_res_checksum              87543
_olex2_submission_special_instructions 'No special instructions were received'