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_7223189
_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, C8 H17 N O'
_chemical_formula_sum            'C18 H24 F3 N O5'
_chemical_formula_weight         391.38
_chemical_melting_point          346.7
_chemical_name_systematic        'Triflusal-valpromide 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
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-24
_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                 114.362(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.8545(8)
_cell_length_b                   5.06409(17)
_cell_length_c                   21.8530(11)
_cell_measurement_reflns_used    12537
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.1150
_cell_measurement_theta_min      3.6210
_cell_volume                     2001.56(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2945
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   46.00  105.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -       21.1986  165.0000  -41.0000 59

  2 omega   24.00  105.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -       21.1986 -165.0000  -63.0000 81

  3 omega   -6.00   57.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -       21.1986 -116.0000   83.0000 63

  4 omega  -75.00  -18.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -      -22.1361  116.0000  171.0000 57

  5 omega -100.00  -74.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -      -22.1361  165.0000  -41.0000 26

  6 omega  -51.00   50.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -       21.1986  -38.0000  150.0000 101

  7 omega   -7.00   87.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -       21.1986   77.0000   90.0000 94

  8 omega  -58.00    1.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -       21.1986  -77.0000  -60.0000 59

  9 omega   -1.00  100.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -       21.1986   77.0000  -30.0000 101

 10 omega -112.00  -81.00   1.0000   17.8500
omega____ theta____ kappa____ phi______ frames
    -      -22.1361 -178.0000   60.0000 31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0188416000
_diffrn_orient_matrix_UB_12      0.0016422000
_diffrn_orient_matrix_UB_13      -0.0214021000
_diffrn_orient_matrix_UB_21      0.0338464000
_diffrn_orient_matrix_UB_22      -0.0256135000
_diffrn_orient_matrix_UB_23      0.0279763000
_diffrn_orient_matrix_UB_31      -0.0061166000
_diffrn_orient_matrix_UB_32      -0.1376528000
_diffrn_orient_matrix_UB_33      -0.0054665000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            35996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         2.712
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       irregular
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         6106
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+1.1125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1167
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5109
_reflns_number_total             6106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ce01756d2.cif
_cod_data_source_block           TRFL-VA
_cod_depositor_comments
'Adding full bibliography for 7223184--7223189.cif.'
_cod_original_cell_volume        2001.57(17)
_cod_database_code               7223189
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'c18 h24 f3 n o5'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 F1, F1A, F3, F3A, C10, F2A, F2, C7, C8, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(F3A)=Sof(F1A)=Sof(F2A)=1-FVAR(1)
 Sof(F1)=Sof(F3)=Sof(F2)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C22(H22)
4.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C26(H26A,H26B), C27(H27A,H27B), C24(H24A,H24B)
4.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C6(H6)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C28(H28A,H28B,H28C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              81076
_olex2_exptl_crystal_mounting_method 'MiTeGen Micromesh'
_olex2_submission_special_instructions 'No special instructions were received'