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_7223187
_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, C3 H7 N O'
_chemical_formula_sum            'C13 H14 F3 N O5'
_chemical_formula_weight         321.25
_chemical_melting_point          333.5
_chemical_name_systematic        'Triflusal-Propionamide cocrystal'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-07-23
_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                 97.605(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.729(6)
_cell_length_b                   9.921(3)
_cell_length_c                   8.067(3)
_cell_measurement_reflns_used    3936
_cell_measurement_temperature    110
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     1485.7(9)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_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: 45.0311
              2theta: -20.1220
scan:
    Number of images: 196
               Slice: -34.7500 - 63.2500
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 90.0000
                 XTD: 45.0311
              2theta: -20.1220
scan:
    Number of images: 204
               Slice: -85.2500 - 16.7500
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -70.0000
                 Phi: 0.0000
                 XTD: 45.0311
              2theta: -20.1220
;
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10698
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         3.005
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.912
_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    1.436
_exptl_crystal_description       Block
_exptl_crystal_F_000             664
_exptl_crystal_preparation       Fiber
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 1,4-Dioxane'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3391
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0635P)^2^+0.3449P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3086
_reflns_number_total             3391
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ce01756d2.cif
_cod_data_source_block           TRFL-PRA
_cod_depositor_comments
'Adding full bibliography for 7223184--7223189.cif.'
_cod_database_code               7223187
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H11C-H11D
 1.5 with sigma of 0.02
 N11A-H11D = N11A-H11C
 0.88 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C11A, O11A, N11A, C12A, H11C, H11D, H12C, H12D, C13A, H13D, H13E, H13F, C11,
 O11, N11, C12, H11A, H11B, H12A, H12B, C13, H13A, H13B, H13C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O11A)=Sof(C11A)=Sof(N11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12C)=
 Sof(H12D)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(1)
 Sof(O11)=Sof(C11)=Sof(N11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C12A(H12C,H12D)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C6(H6)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C), C13A(H13D,H13E,H13F)
;
_shelx_res_checksum              6843
_olex2_submission_special_instructions 'No special instructions were received'