Physicochemical and thermodynamic evaluation of ibrutinib cocrystal formation with a long-chain fatty acid
Tiwari, Shubhanshu Ranjan; Gopi, Shanmukha Prasad; Kallem, Divya Jyothi; Chaturvedi, Deepika; Voguri, Raja Sekhar; Ramakrishnan, Srividya; Dey, Archan; Pal, Sharmistha; CrystEngComm 25 (2023) 601–613; doi:10.1039/D2CE01216B

data_7245994
_publ_section_title
;
 Physicochemical and thermodynamic evaluation of ibrutinib cocrystal
 formation with a long-chain fatty acid
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              601
_journal_page_last               613
_journal_paper_doi               10.1039/D2CE01216B
_journal_volume                  25
_journal_year                    2023
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C25 H24 N6 O2, C16 H32 O2'
_chemical_formula_sum            'C41 H56 N6 O4'
_chemical_formula_weight         696.91
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-07-01 deposited with the CCDC.	2022-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.685(2)
_cell_length_b                   9.764(3)
_cell_length_c                   52.921(16)
_cell_measurement_reflns_used    6096
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.19
_cell_measurement_theta_min      2.55
_cell_volume                     3971(2)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  '<i>SHELXL2014</i> (Sheldrick, 2015)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_limit_l_min       -62
_diffrn_reflns_number            21363
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.223
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1488 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(8)
_refine_ls_extinction_coef       0.0048(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0599
_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^)+(0.0466P)^2^+1.2343P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1385
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4626
_reflns_number_total             6975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01216b2.cif
_cod_data_source_block           KA407_0M
_cod_depositor_comments          'Adding full bibliography for 7245994.cif.'
_cod_database_code               7245994
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              82470
_shelx_hkl_checksum              23828