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_7232881
_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
_atom_sites_solution_primary     dual
_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                79.683(14)
_cell_angle_beta                 85.829(11)
_cell_angle_gamma                79.844(14)
_cell_formula_units_Z            2
_cell_length_a                   7.0133(6)
_cell_length_b                   10.155(2)
_cell_length_c                   16.607(3)
_cell_measurement_reflns_used    599
_cell_measurement_temperature    297
_cell_measurement_theta_max      18.906
_cell_measurement_theta_min      3.157
_cell_volume                     1144.4(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_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 0.309
_diffrn_measured_fraction_theta_max 0.309
_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  0.0734
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.309
_diffrn_reflns_Laue_measured_fraction_max 0.309
_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            3840
_diffrn_reflns_point_group_measured_fraction_full 0.309
_diffrn_reflns_point_group_measured_fraction_max 0.309
_diffrn_reflns_theta_full        23.224
_diffrn_reflns_theta_max         23.224
_diffrn_reflns_theta_min         2.953
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1025 before and 0.0509 after correction. The Ratio of minimum to maximum transmission is 0.8711. 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    1.570
_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         0.275
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1015
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0657
_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^)+(0.0626P)^2^+3.4878P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1662
_reflns_Friedel_coverage         0.000
_reflns_number_gt                682
_reflns_number_total             1015
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce00838a2.cif
_cod_data_source_block           insa_0p55GPa
_cod_depositor_comments
'Adding full bibliography for 7232876--7232882.cif.'
_cod_original_cell_volume        1144.3(3)
_cod_database_code               7232881
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.926
_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
 O17-C15
 1.215 with sigma of 0.02
 C15-O16
 1.303 with sigma of 0.02
 C15-C14
 1.503 with sigma of 0.02
 C14-C13
 1.494 with sigma of 0.02
 C18-C13
 1.438 with sigma of 0.02
 C11-C13
 1.357 with sigma of 0.02
 C12-C11
 1.492 with sigma of 0.02
 C11-N10
 1.42 with sigma of 0.02
 N10-C25
 1.419 with sigma of 0.02
 N10-C8
 1.398 with sigma of 0.02
 O9-C8
 1.21 with sigma of 0.02
 C8-C5
 1.489 with sigma of 0.02
 C2-Cl1
 1.744 with sigma of 0.02
 C34-S35
 1.75 with sigma of 0.02
 S35-O37
 1.426 with sigma of 0.02
 S35-O36
 1.421 with sigma of 0.02
 N26-S35
 1.653 with sigma of 0.02
 C27-N26
 1.378 with sigma of 0.02
 C27-C29
 1.483 with sigma of 0.02
 O28-C27
 1.211 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b)
4.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)
4.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)
4.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C22(H22a,H22b,H22c)
4.e Idealised tetrahedral OH refined as rotating group:
 O16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'