Structural investigation and compression of a co-crystal of indomethacin and saccharin
Connor, Lauren E.; Vassileiou, Antony D.; Halbert, Gavin W.; Johnston, Blair F.; Oswald, Iain D. H.; CrystEngComm 21 (2019) 4465–; doi:10.1039/C9CE00838A

data_7232878
_publ_section_title
;
 Structural investigation and compression of a co-crystal of indomethacin
 and saccharin
;
_journal_issue                   30
_journal_name_full               CrystEngComm
_journal_page_first              4465
_journal_paper_doi               10.1039/C9CE00838A
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C19 H16 Cl N O4, C7 H5 N O3 S'
_chemical_formula_sum            'C26 H21 Cl N2 O7 S'
_chemical_formula_weight         540.96
_chemical_name_systematic
'?1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid 1,2-benzisothiazol-3(2H)-one 1,1-dioxide'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-02-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-10 deposited with the CCDC.    2019-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                77.764(8)
_cell_angle_beta                 84.858(6)
_cell_angle_gamma                81.297(8)
_cell_formula_units_Z            2
_cell_length_a                   6.7888(3)
_cell_length_b                   9.6045(11)
_cell_length_c                   16.3703(16)
_cell_measurement_reflns_used    1371
_cell_measurement_temperature    297
_cell_measurement_theta_max      22.422
_cell_measurement_theta_min      3.227
_cell_volume                     1029.30(17)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      297.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.314
_diffrn_measured_fraction_theta_max 0.314
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.314
_diffrn_reflns_Laue_measured_fraction_max 0.314
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4793
_diffrn_reflns_point_group_measured_fraction_full 0.314
_diffrn_reflns_point_group_measured_fraction_max 0.314
_diffrn_reflns_theta_full        23.324
_diffrn_reflns_theta_max         23.324
_diffrn_reflns_theta_min         3.041
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0729 before and 0.0488 after correction. The Ratio of minimum to maximum transmission is 0.9098. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_recrystallization_method
'Recrystallised from a 1:1 molar ratio of indomethacin and saccharin from ethyl acetate'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         941
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0639
_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^)+(0.0584P)^2^+5.4456P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1627
_reflns_Friedel_coverage         0.000
_reflns_number_gt                747
_reflns_number_total             941
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce00838a2.cif
_cod_data_source_block           insa_3p33GPa
_cod_depositor_comments
'Adding full bibliography for 7232876--7232882.cif.'
_cod_database_code               7232878
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.918
_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, All O(H) groups
2. Restrained distances
 C2-Cl1
 0.011 with sigma of 1.742
 C5-C8
 0.011 with sigma of 1.495
 O9-C8
 0.013 with sigma of 1.217
 C8-N10
 0.021 with sigma of 1.413
 C11-N10
 0.018 with sigma of 1.398
 C25-N10
 0.015 with sigma of 1.415
 C12-C11
 0.01 with sigma of 1.491
 C11-C13
 0.007 with sigma of 1.355
 C14-C13
 0.009 with sigma of 1.502
 C18-C13
 0.015 with sigma of 1.437
 C14-C15
 0.008 with sigma of 1.506
 O16-C15
 0.023 with sigma of 1.307
 O17-C15
 0.021 with sigma of 1.213
 C19-C18
 0.012 with sigma of 1.395
 C18-C25
 0.01 with sigma of 1.406
 O21-C20
 0.011 with sigma of 1.369
 O21-C22
 0.015 with sigma of 1.425
 C27-N26
 0.013 with sigma of 1.374
 S35-N26
 0.015 with sigma of 1.654
 O28-C27
 0.011 with sigma of 1.228
 C29-C27
 0.012 with sigma of 1.483
 C34-S35
 0.008 with sigma of 1.753
 O36-S35
 0.007 with sigma of 1.431
 O37-S35
 0.007 with sigma of 1.431
3.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C3(H3), C23(H23), C24(H24), C19(H19), N26(H26),
 C30(H30), C31(H31), C32(H32), C33(H33)
3.c Fitted hexagon refined as free rotating group:
 C4(C5,C6,C7,C2,C3), C23(C24,C25,C18,C19,C20), C34(C29,C30,C31,C32,C33)
3.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C22(H22a,H22b,H22c)
3.e Idealised tetrahedral OH refined as rotating group:
 O16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'