The first zwitterionic cocrystal of indomethacin with amino acid showing optimized physicochemical properties as well as accelerated absorption and slowed elimination in vivo
Wang, Ling-Yang; Yu, Yue-Ming; Jiang, Fu-Bin; Li, Yan-Tuan; Wu, Zhi-Yong; Yan, Cui-Wei; New Journal of Chemistry 44 (2020) 3930–3939; doi:10.1039/C9NJ06180K

data_7059255
_publ_section_title
;
 The first zwitterionic cocrystal of indomethacin with amino acid showing
 optimized physicochemical properties as well as accelerated absorption
 and slowed elimination in vivo
;
_journal_issue                   10
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3930
_journal_page_last               3939
_journal_paper_doi               10.1039/C9NJ06180K
_journal_volume                  44
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_sum            'C24 H27 Cl N2 O7'
_chemical_formula_weight         490.92
_chemical_name_common            'indomethacin L-proline'
_chemical_name_systematic
'1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid L-proline'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-12-13 deposited with the CCDC.	2020-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.436(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.4240(5)
_cell_length_b                   5.7358(2)
_cell_length_c                   16.3820(6)
_cell_measurement_reflns_used    3591
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.363
_cell_measurement_theta_min      4.098
_cell_volume                     1144.23(8)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7252
_diffrn_reflns_point_group_measured_fraction_full 0.812
_diffrn_reflns_point_group_measured_fraction_max 0.785
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.363
_diffrn_reflns_theta_min         4.098
_exptl_absorpt_coefficient_mu    1.903
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       needle
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.820
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3591
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0788
_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^)+(0.1596P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2035
_refine_ls_wR_factor_ref         0.2096
_reflns_Friedel_coverage         0.448
_reflns_Friedel_fraction_full    0.579
_reflns_Friedel_fraction_max     0.543
_reflns_number_gt                3276
_reflns_number_total             3591
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj06180k2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;Adding full bibliography for 7059255.cif.

 Adding full bibliography for 7059255.cif.
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7059255
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.599
_shelx_estimated_absorpt_t_max   0.832
_shelx_res_checksum              22671