#------------------------------------------------------------------------------
#$Date: 2016-01-09 12:29:05 +0200 (Sat, 09 Jan 2016) $
#$Revision: 173752 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/31/7223188.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7223188
loop_
_publ_author_name
'Aitipamula, Srinivasulu'
'Mapp, Lucy K.'
'Wong, Annie B. H.'
'Chow, Pui Shan'
'Tan, Reginald B. H.'
_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         'C H4 N2 O, 2(C10 H7 F3 O4)'
_chemical_formula_sum            'C21 H18 F6 N2 O9'
_chemical_formula_weight         556.37
_chemical_melting_point          356.4
_chemical_name_systematic        'Triflusal-urea cocrystal'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-07-06
_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                 102.49(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.601(3)
_cell_length_b                   10.920(2)
_cell_length_c                   15.342(3)
_cell_measurement_reflns_used    3920
_cell_measurement_temperature    110.1500
_cell_measurement_theta_max      30.9639
_cell_measurement_theta_min      2.3495
_cell_volume                     2388.3(9)
_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      110.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
scan:
    Number of images: 330
               Slice: -110.0000 - 55.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 270.0000
                 XTD: 45.0093
              2theta: -20.0682
scan:
    Number of images: 262
               Slice: -110.0000 - 21.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -70.0000
                 Phi: 270.0000
                 XTD: 45.0093
              2theta: -20.0682
scan:
    Number of images: 262
               Slice: -110.0000 - 21.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -70.0000
                 Phi: 90.0000
                 XTD: 45.0093
              2theta: -20.0682
scan:
    Number of images: 246
               Slice: -110.0000 - 13.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -70.0000
                 Phi: 0.0000
                 XTD: 45.0093
              2theta: -20.0682
scan:
    Number of images: 120
               Slice: -95.0000 - -35.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 0.0000
                 XTD: 45.0093
              2theta: -20.0682
;
_diffrn_measurement_device
;
Saturn70 (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0583
_diffrn_orient_matrix_UB_12      -0.0359
_diffrn_orient_matrix_UB_13      0.0152
_diffrn_orient_matrix_UB_21      0.0231
_diffrn_orient_matrix_UB_22      -0.0637
_diffrn_orient_matrix_UB_23      -0.0616
_diffrn_orient_matrix_UB_31      0.0203
_diffrn_orient_matrix_UB_32      -0.0403
_diffrn_orient_matrix_UB_33      0.0492
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_laue_measured_fraction_full 0.991
_diffrn_reflns_laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15825
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         2.555
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.9495
_exptl_absorpt_correction_T_min  .9371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst. 1995 A51, 33-38'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Tetrahydrofuran'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0396
_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/[σ²(Fo²)+(0.0600P)²+2.0078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1079
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2913
_reflns_number_total             2944
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ce01756d2.cif
_cod_data_source_block           TRFL-Urea
_cod_depositor_comments
'Adding full bibliography for 7223184--7223189.cif.'
_cod_original_cell_volume        2388.2(9)
_cod_database_code               7223188
_shelxl_version_number           2013-4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.937
_diffrn_number_total             3682
_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) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C8(H8)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O11 O 0.0000 0.62178(10) 0.2500 0.0227(2) Uani 1 2 d S T P
N11 N 0.05970(7) 0.44407(9) 0.21111(7) 0.0198(2) Uani 1 1 d . . .
C11 C 0.0000 0.50581(14) 0.2500 0.0176(3) Uani 1 2 d S T P
F3 F 0.14171(6) 0.74390(7) 0.43768(6) 0.0314(2) Uani 1 1 d . . .
F2 F 0.16438(6) 0.64215(7) 0.56017(5) 0.0311(2) Uani 1 1 d . . .
F1 F 0.03745(5) 0.61597(7) 0.46101(6) 0.0318(2) Uani 1 1 d . . .
O2 O 0.15891(6) 0.20218(7) 0.41330(5) 0.01963(18) Uani 1 1 d . . .
O3 O 0.31217(6) 0.13231(8) 0.34740(6) 0.0247(2) Uani 1 1 d . . .
O1 O 0.10733(6) 0.17886(8) 0.26425(6) 0.0250(2) Uani 1 1 d . . .
O4 O 0.38922(7) 0.28132(9) 0.29439(8) 0.0350(3) Uani 1 1 d . . .
C6 C 0.25091(8) 0.55942(10) 0.38986(8) 0.0209(2) Uani 1 1 d . . .
H6 H 0.2700 0.6417 0.3842 0.025 Uiso 1 1 calc R . .
C3 C 0.19161(7) 0.31945(10) 0.40219(7) 0.0168(2) Uani 1 1 d . . .
C5 C 0.29651(8) 0.46344(10) 0.35758(8) 0.0204(2) Uani 1 1 d . . .
H5 H 0.3477 0.4809 0.3304 0.024 Uiso 1 1 calc R . .
C2 C 0.12157(8) 0.13631(10) 0.33824(8) 0.0207(2) Uani 1 1 d . . .
C8 C 0.14649(7) 0.41367(10) 0.43635(7) 0.0176(2) Uani 1 1 d . . .
H8 H 0.0952 0.3967 0.4635 0.021 Uiso 1 1 calc R . .
C4 C 0.26886(7) 0.34179(10) 0.36414(7) 0.0177(2) Uani 1 1 d . . .
C7 C 0.17694(7) 0.53336(10) 0.43055(7) 0.0183(2) Uani 1 1 d . . .
C9 C 0.32423(8) 0.24040(10) 0.33442(7) 0.0193(2) Uani 1 1 d . . .
C10 C 0.12992(8) 0.63384(10) 0.47157(8) 0.0214(2) Uani 1 1 d . . .
C1 C 0.10159(10) 0.00835(11) 0.36284(9) 0.0311(3) Uani 1 1 d . . .
H1A H 0.0555 -0.0288 0.3140 0.047 Uiso 1 1 calc GR . .
H1B H 0.0764 0.0094 0.4171 0.047 Uiso 1 1 calc GR . .
H1C H 0.1597 -0.0396 0.3736 0.047 Uiso 1 1 calc GR . .
H11A H 0.1002(12) 0.4872(16) 0.1903(11) 0.030(4) Uiso 1 1 d . . .
H11B H 0.0674(12) 0.3667(16) 0.2197(11) 0.029(4) Uiso 1 1 d . . .
H4 H 0.4257(16) 0.221(2) 0.2805(15) 0.060(6) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C11 N11 H11A 116.8(11) . .
C11 N11 H11B 120.2(12) . .
H11A N11 H11B 120.8(16) . .
O11 C11 N11 120.21(7) . 2
O11 C11 N11 120.21(7) . .
N11 C11 N11 119.58(15) 2 .
C2 O2 C3 117.80(9) . .
C9 O4 H4 112.7(15) . .
C5 C6 H6 120.5 . .
C7 C6 H6 120.5 . .
C7 C6 C5 119.01(10) . .
O2 C3 C4 122.76(10) . .
C8 C3 O2 115.72(9) . .
C8 C3 C4 121.40(10) . .
C6 C5 H5 119.2 . .
C6 C5 C4 121.53(10) . .
C4 C5 H5 119.2 . .
O2 C2 C1 110.10(10) . .
O1 C2 O2 123.22(10) . .
O1 C2 C1 126.67(11) . .
C3 C8 H8 120.3 . .
C3 C8 C7 119.32(10) . .
C7 C8 H8 120.3 . .
C3 C4 C9 122.32(10) . .
C5 C4 C3 117.85(10) . .
C5 C4 C9 119.78(10) . .
C6 C7 C8 120.81(10) . .
C6 C7 C10 120.58(10) . .
C8 C7 C10 118.59(10) . .
O3 C9 O4 123.43(10) . .
O3 C9 C4 124.08(10) . .
O4 C9 C4 112.47(10) . .
F3 C10 F2 106.31(9) . .
F3 C10 F1 107.19(10) . .
F3 C10 C7 112.65(10) . .
F2 C10 C7 111.54(10) . .
F1 C10 F2 106.19(10) . .
F1 C10 C7 112.52(9) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O11 C11 1.2664(19) .
N11 C11 1.3399(12) .
N11 H11A 0.869(18) .
N11 H11B 0.859(18) .
C11 N11 1.3399(12) 2
F3 C10 1.3353(13) .
F2 C10 1.3466(14) .
F1 C10 1.3388(14) .
O2 C3 1.3901(13) .
O2 C2 1.3672(14) .
O3 C9 1.2162(14) .
O1 C2 1.2024(15) .
O4 C9 1.3151(14) .
O4 H4 0.90(2) .
C6 H6 0.9500 .
C6 C5 1.3891(15) .
C6 C7 1.3887(15) .
C3 C8 1.3844(15) .
C3 C4 1.3989(15) .
C5 H5 0.9500 .
C5 C4 1.3984(15) .
C2 C1 1.4925(16) .
C8 H8 0.9500 .
C8 C7 1.3896(15) .
C4 C9 1.4989(15) .
C7 C10 1.5027(15) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11A O3 0.869(18) 2.192(18) 3.0426(14) 166.3(16) 4
N11 H11B O1 0.859(18) 2.200(18) 3.0480(14) 169.1(15) .
O4 H4 O11 0.90(2) 1.67(2) 2.5673(12) 174(2) 3_545
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O2 C3 C8 C7 177.94(9)
O2 C3 C4 C5 -178.99(9)
O2 C3 C4 C9 -1.65(16)
C6 C5 C4 C3 1.77(17)
C6 C5 C4 C9 -175.64(10)
C6 C7 C10 F3 22.58(15)
C6 C7 C10 F2 -96.89(13)
C6 C7 C10 F1 143.89(11)
C3 O2 C2 O1 -7.57(16)
C3 O2 C2 C1 172.90(9)
C3 C8 C7 C6 0.95(16)
C3 C8 C7 C10 -177.33(10)
C3 C4 C9 O3 -6.43(18)
C3 C4 C9 O4 175.12(11)
C5 C6 C7 C8 -2.23(17)
C5 C6 C7 C10 176.02(10)
C5 C4 C9 O3 170.86(11)
C5 C4 C9 O4 -7.60(15)
C2 O2 C3 C8 117.80(11)
C2 O2 C3 C4 -66.09(14)
C8 C3 C4 C5 -3.09(16)
C8 C3 C4 C9 174.25(10)
C8 C7 C10 F3 -159.13(10)
C8 C7 C10 F2 81.40(13)
C8 C7 C10 F1 -37.81(15)
C4 C3 C8 C7 1.77(16)
C7 C6 C5 C4 0.83(17)
