#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/79/7117955.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_7117955
loop_
_publ_author_name
'Geetha Bolla'
'Ashwini Nangia'
_publ_section_title
;
 Multicomponent ternary cocrystals of the sulfonamide group with
 pyridine-amides and lactams
;
_journal_name_full               Chem.Commun.
_journal_page_first              15578
_journal_paper_doi               10.1039/C5cc06475A
_journal_volume                  51
_journal_year                    2015
_chemical_compound_source        synthetic
_chemical_formula_moiety         C7H7NO4S,C6H6N2O
_chemical_formula_sum            'C13 H13 N3 O5 S'
_chemical_formula_weight         323.32
_chemical_melting_point          448
_chemical_name_common            'Sulfonamide benzoic acid; isonicotinamide'
_chemical_name_systematic        'Sulfonamide benzoic acid; isonicotina'
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-07-22 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 124.550(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.237(4)
_cell_length_b                   5.1056(6)
_cell_length_c                   20.362(2)
_cell_measurement_reflns_used    2840
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.29
_cell_measurement_theta_min      2.43
_cell_volume                     2674.7(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13340
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLES
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             1344
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOAc, THF'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0755P)²+0.0763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1198
_reflns_number_gt                2209
_reflns_number_total             2742
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc06475a2.cif
_cod_data_source_block           SMBAINA11
_cod_original_cell_volume        2674.6(6)
_cod_original_sg_symbol_H-M      'C2/c '
_cod_database_code               7117955
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.231297(19) 0.71776(10) 0.13534(3) 0.02831(18) Uani 1 1 d . . .
O4 O 0.13522(5) -0.1403(3) -0.16182(8) 0.0309(3) Uani 1 1 d . . .
O5 O 0.07564(5) -0.2015(3) -0.13618(9) 0.0360(4) Uani 1 1 d . . .
C4 C 0.13933(7) 0.1313(4) -0.06462(11) 0.0261(4) Uani 1 1 d . . .
C7 C 0.11355(7) -0.0844(4) -0.12423(11) 0.0263(4) Uani 1 1 d . . .
O2 O 0.20421(6) 0.7618(3) 0.17171(9) 0.0446(4) Uani 1 1 d . . .
C2 C 0.20445(7) 0.4661(4) -0.00076(11) 0.0301(5) Uani 1 1 d . . .
H2 H 0.2303 0.5666 0.0021 0.036 Uiso 1 1 calc R . .
C3 C 0.17801(8) 0.2813(4) -0.05983(12) 0.0288(4) Uani 1 1 d . . .
H3 H 0.1861 0.2568 -0.0968 0.035 Uiso 1 1 calc R . .
O1 O 0.24577(6) 0.9314(3) 0.10689(8) 0.0401(4) Uani 1 1 d . . .
C1 C 0.19237(7) 0.5016(4) 0.05456(11) 0.0269(4) Uani 1 1 d . . .
C5 C 0.12612(8) 0.1769(4) -0.01111(12) 0.0332(5) Uani 1 1 d . . .
H5 H 0.0991 0.0828 -0.0157 0.040 Uiso 1 1 calc R . .
N1 N 0.28415(7) 0.5720(4) 0.20000(11) 0.0376(5) Uani 1 1 d . . .
C6 C 0.15268(8) 0.3604(4) 0.04892(12) 0.0331(5) Uani 1 1 d . . .
H6 H 0.1439 0.3885 0.0851 0.040 Uiso 1 1 calc R . .
N2 N 0.09443(6) 0.5395(3) 0.24272(9) 0.0296(4) Uani 1 1 d . . .
O3 O 0.04744(6) 1.2447(3) 0.04493(9) 0.0366(4) Uani 1 1 d . . .
N3 N -0.01520(7) 1.3030(4) 0.06537(11) 0.0316(4) Uani 1 1 d . . .
C8 C 0.04864(7) 0.9565(4) 0.13688(11) 0.0258(4) Uani 1 1 d . . .
C13 C 0.02628(7) 1.1808(4) 0.07818(11) 0.0257(4) Uani 1 1 d . . .
C9 C 0.09232(8) 0.8322(4) 0.15029(12) 0.0305(5) Uani 1 1 d . . .
H9 H 0.1070 0.8876 0.1237 0.037 Uiso 1 1 calc R . .
C11 C 0.05275(8) 0.6610(4) 0.23063(12) 0.0323(5) Uani 1 1 d . . .
H11 H 0.0392 0.6033 0.2586 0.039 Uiso 1 1 calc R . .
C12 C 0.02886(8) 0.8676(4) 0.17876(12) 0.0319(5) Uani 1 1 d . . .
H12 H -0.0002 0.9465 0.1719 0.038 Uiso 1 1 calc R . .
C10 C 0.11392(8) 0.6270(4) 0.20301(12) 0.0314(5) Uani 1 1 d . . .
H10 H 0.1433 0.5457 0.2114 0.038 Uiso 1 1 calc R . .
H3A H -0.0313(10) 1.264(5) 0.0892(15) 0.047(7) Uiso 1 1 d . . .
H3B H -0.0274(8) 1.425(5) 0.0310(13) 0.036(6) Uiso 1 1 d . . .
H1A H 0.3036(10) 0.543(5) 0.1841(16) 0.057(8) Uiso 1 1 d . . .
H1B H 0.2813(9) 0.457(6) 0.2280(15) 0.051(7) Uiso 1 1 d . . .
H4A H 0.1176(12) -0.300(7) -0.2007(19) 0.086(10) 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'
S S 0.1246 0.1234 '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
O2 S1 O1 120.70(10) . .
O2 S1 N1 106.64(11) . .
O1 S1 N1 105.91(10) . .
O2 S1 C1 106.51(9) . .
O1 S1 C1 108.00(9) . .
N1 S1 C1 108.66(10) . .
C5 C4 C3 119.22(18) . .
C5 C4 C7 119.95(17) . .
C3 C4 C7 120.78(17) . .
O5 C7 O4 122.78(18) . .
O5 C7 C4 122.57(17) . .
O4 C7 C4 114.65(16) . .
C3 C2 C1 119.64(18) . .
C2 C3 C4 120.49(18) . .
C6 C1 C2 120.58(18) . .
C6 C1 S1 120.90(14) . .
C2 C1 S1 118.42(15) . .
C6 C5 C4 120.79(18) . .
C1 C6 C5 119.17(18) . .
C11 N2 C10 117.75(17) . .
C12 C8 C9 117.57(18) . .
C12 C8 C13 124.70(17) . .
C9 C8 C13 117.73(17) . .
O3 C13 N3 122.60(18) . .
O3 C13 C8 119.05(17) . .
N3 C13 C8 118.35(17) . .
C10 C9 C8 119.77(18) . .
N2 C11 C12 123.13(18) . .
C11 C12 C8 119.21(18) . .
N2 C10 C9 122.57(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.4233(15) .
S1 O1 1.4237(15) .
S1 N1 1.596(2) .
S1 C1 1.770(2) .
O4 C7 1.309(2) .
O5 C7 1.221(2) .
C4 C5 1.386(3) .
C4 C3 1.386(3) .
C4 C7 1.492(3) .
C2 C3 1.376(3) .
C2 C1 1.388(3) .
C1 C6 1.382(3) .
C5 C6 1.382(3) .
N2 C11 1.333(2) .
N2 C10 1.335(2) .
O3 C13 1.228(2) .
N3 C13 1.324(3) .
C8 C12 1.383(3) .
C8 C9 1.385(3) .
C8 C13 1.510(3) .
C9 C10 1.373(3) .
C11 C12 1.375(3) .
