Novel pharmaceutical cocrystals of triflusal: crystal engineering and physicochemical characterization
Aitipamula, Srinivasulu; Mapp, Lucy K.; Wong, Annie B. H.; Chow, Pui Shan; Tan, Reginald B. H.; CrystEngComm 17 (2015) 9323–; doi:10.1039/C5CE01756D

data_7223185
_publ_section_title
;
 Novel pharmaceutical cocrystals of triflusal: crystal engineering and
 physicochemical characterization
;
_journal_issue                   48
_journal_name_full               CrystEngComm
_journal_page_first              9323
_journal_paper_doi               10.1039/C5CE01756D
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C10 H7 F3 O4, C6 H6 N2 O'
_chemical_formula_sum            'C16 H13 F3 N2 O5'
_chemical_formula_weight         370.28
_chemical_melting_point          406.1
_chemical_name_systematic        'Triflusal-Isonicotinamide cocrystal'
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-08-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-08-31 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.506(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.345(7)
_cell_length_b                   5.1415(17)
_cell_length_c                   19.447(7)
_cell_measurement_reflns_used    4030
_cell_measurement_temperature    110
_cell_measurement_theta_max      30.9493
_cell_measurement_theta_min      2.2683
_cell_volume                     1602.2(10)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
????
;
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
scan:
    Number of images: 300
               Slice: -110.0000 - 40.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 90.0000
                 XTD: 45.0292
              2theta: -20.2668
scan:
    Number of images: 202
               Slice: -110.0000 - -9.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -70.0000
                 Phi: 0.0000
                 XTD: 45.0292
              2theta: -20.2668
scan:
    Number of images: 182
               Slice: -61.0000 - 30.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 90.0000
                 XTD: 45.0292
              2theta: -20.2668
;
_diffrn_measurement_device
;
Saturn70 (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0105
_diffrn_orient_matrix_UB_12      0.0469
_diffrn_orient_matrix_UB_13      -0.0398
_diffrn_orient_matrix_UB_21      -0.0361
_diffrn_orient_matrix_UB_22      -0.1188
_diffrn_orient_matrix_UB_23      -0.1497
_diffrn_orient_matrix_UB_31      -0.0462
_diffrn_orient_matrix_UB_32      0.0288
_diffrn_orient_matrix_UB_33      -0.0117
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10874
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.463
_diffrn_reflns_theta_min         2.994
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst. 1995 A51, 33-38'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       Prism
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Tetrahydrofuran'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3648
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0559
_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^)+(0.1010P)^2^+0.2281P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1782
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3078
_reflns_number_total             3648
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ce01756d2.cif
_cod_data_source_block           TRFL-INA
_cod_depositor_comments
'Adding full bibliography for 7223184--7223189.cif.'
_cod_database_code               7223185
_shelxl_version_number           2013-4
_diffrn_number_total             5004
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Restrained distances
 O4-H4
 0.84 with sigma of 0.02
3. Others
 Sof(H1BD)=Sof(H1BE)=Sof(H1BF)=Sof(O1A)=Sof(O2A)=Sof(C2A)=Sof(C3A)=Sof(C8A)=
 Sof(H8A)=1-FVAR(1)
 Sof(O2)=Sof(C8)=Sof(H8)=Sof(C3)=Sof(O1)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C2)=
 FVAR(1)
4.a Me refined with riding coordinates:
 C1(H1AA,H1AB,H1AC), C1(H1BD,H1BE,H1BF)
4.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C14(H14), C15(H15), C13(H13), C6(H6), C5(H5), C8(H8), C8A(H8A)
;
_shelx_res_checksum              23850
_olex2_submission_special_instructions 'No special instructions were received'