#------------------------------------------------------------------------------
#$Date: 2015-10-20 17:01:13 +0300 (Tue, 20 Oct 2015) $
#$Revision: 169191 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/79/7117962.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_7117962
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,2(C6H7NO2)
_chemical_formula_sum            'C19 H21 N3 O8 S'
_chemical_formula_weight         451.45
_chemical_melting_point          441
_chemical_name_common
'Sulfonamide benzoic acid; 3methoxy 2pyridone'
_chemical_name_systematic
'Sulfonamide benzoic acid; 3methoxy 2pyridone'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.737(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.95437(16)
_cell_length_b                   12.7192(3)
_cell_length_c                   23.9115(5)
_cell_measurement_reflns_used    4514
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      71.9930
_cell_measurement_theta_min      5.0510
_cell_volume                     2112.66(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7314
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.70
_exptl_absorpt_coefficient_mu    1.826
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63770
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLORLES
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             944
_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         0.332
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0410
_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)+(0.0667P)²+0.4850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                3447
_reflns_number_total             3756
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc06475a2.cif
_cod_data_source_block           SMBAOMEHP12
_cod_database_code               7117962
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 -0.05675(6) 0.12840(3) 0.063909(17) 0.04101(15) Uani 1 1 d . . .
O1 O -0.13000(18) 0.02328(10) 0.06300(5) 0.0508(3) Uani 1 1 d . . .
O7 O 0.0859(2) 0.37563(10) 0.99686(7) 0.0647(4) Uani 1 1 d . . .
O8 O 0.3679(2) 0.25044(10) 0.96828(7) 0.0601(4) Uani 1 1 d . . .
C1 C 0.1616(2) 0.12947(13) 0.10581(7) 0.0410(4) Uani 1 1 d . . .
N3 N 0.2199(2) 0.51554(12) 0.95462(7) 0.0521(4) Uani 1 1 d . . .
H3A H 0.1262 0.5544 0.9645 0.063 Uiso 1 1 calc R . .
O4 O 0.7510(2) 0.23008(11) 0.21641(6) 0.0575(4) Uani 1 1 d . . .
C4 C 0.5087(3) 0.13615(14) 0.16556(7) 0.0443(4) Uani 1 1 d . . .
O3 O 0.7966(2) 0.05870(11) 0.20295(6) 0.0613(4) Uani 1 1 d . . .
O2 O -0.17381(19) 0.21142(11) 0.08352(6) 0.0544(3) Uani 1 1 d . . .
C6 C 0.2665(3) 0.03841(15) 0.11337(9) 0.0554(5) Uani 1 1 d . . .
H6 H 0.2207 -0.0248 0.0985 0.066 Uiso 1 1 calc R . .
C3 C 0.4005(3) 0.22600(15) 0.15841(8) 0.0512(4) Uani 1 1 d . . .
H3 H 0.4456 0.2891 0.1737 0.061 Uiso 1 1 calc R . .
C15 C 0.3785(3) 0.35148(14) 0.95194(8) 0.0465(4) Uani 1 1 d . . .
N1 N -0.0051(2) 0.15699(14) 0.00108(7) 0.0486(4) Uani 1 1 d . . .
H1A H 0.046(3) 0.219(2) -0.0002(9) 0.058 Uiso 1 1 d . . .
C7 C 0.7002(3) 0.13746(15) 0.19672(8) 0.0476(4) Uani 1 1 d . . .
C14 C 0.2182(3) 0.41306(14) 0.96954(8) 0.0465(4) Uani 1 1 d . . .
C5 C 0.4406(3) 0.04243(16) 0.14338(9) 0.0572(5) Uani 1 1 d . . .
H5 H 0.5129 -0.0186 0.1487 0.069 Uiso 1 1 calc R . .
C2 C 0.2252(3) 0.22342(15) 0.12871(8) 0.0516(4) Uani 1 1 d . . .
H2 H 0.1513 0.2841 0.1242 0.062 Uiso 1 1 calc R . .
C16 C 0.5183(3) 0.39651(17) 0.92239(9) 0.0590(5) Uani 1 1 d . . .
H16 H 0.6218 0.3564 0.9114 0.071 Uiso 1 1 calc R . .
C18 C 0.3600(3) 0.56135(17) 0.92510(10) 0.0636(5) Uani 1 1 d . . .
H18 H 0.3534 0.6327 0.9166 0.076 Uiso 1 1 calc R . .
C17 C 0.5074(4) 0.50354(18) 0.90829(11) 0.0694(6) Uani 1 1 d . . .
H17 H 0.6020 0.5341 0.8874 0.083 Uiso 1 1 calc R . .
C19 C 0.5151(4) 0.1811(2) 0.95192(14) 0.0834(8) Uani 1 1 d . . .
H19A H 0.5217 0.1824 0.9119 0.125 Uiso 1 1 calc R . .
H19B H 0.4868 0.1110 0.9639 0.125 Uiso 1 1 calc R . .
H19C H 0.6364 0.2031 0.9689 0.125 Uiso 1 1 calc R . .
O5 O 0.4277(2) 0.73482(11) 0.22773(7) 0.0632(4) Uani 1 1 d . . .
N2 N 0.3444(2) 0.56304(12) 0.23703(7) 0.0515(4) Uani 1 1 d . . .
H2A H 0.4534 0.5512 0.2544 0.062 Uiso 1 1 calc R . .
O6 O 0.0934(2) 0.77949(12) 0.17565(7) 0.0645(4) Uani 1 1 d . . .
C12 C 0.2213(3) 0.48010(16) 0.22964(9) 0.0576(5) Uani 1 1 d . . .
H12 H 0.2542 0.4143 0.2441 0.069 Uiso 1 1 calc R . .
C9 C 0.1236(3) 0.67794(16) 0.19019(7) 0.0500(4) Uani 1 1 d . . .
C10 C 0.0024(3) 0.59578(17) 0.18082(8) 0.0555(5) Uani 1 1 d . . .
H10 H -0.1142 0.6060 0.1609 0.067 Uiso 1 1 calc R . .
C8 C 0.3085(3) 0.66211(15) 0.21923(7) 0.0488(4) Uani 1 1 d . . .
C11 C 0.0520(3) 0.49444(17) 0.20122(9) 0.0610(5) Uani 1 1 d . . .
H11 H -0.0318 0.4382 0.1950 0.073 Uiso 1 1 calc R . .
C13 C -0.0904(3) 0.80554(19) 0.15047(10) 0.0694(6) Uani 1 1 d . . .
H13A H -0.1064 0.7712 0.1148 0.104 Uiso 1 1 calc R . .
H13B H -0.0990 0.8803 0.1454 0.104 Uiso 1 1 calc R . .
H13C H -0.1895 0.7826 0.1743 0.104 Uiso 1 1 calc R . .
H1B H 0.056(3) 0.1028(19) -0.0161(9) 0.059(6) Uiso 1 1 d . . .
H4A H 0.884(5) 0.224(2) 0.2370(14) 0.112(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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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 119.25(8) . .
O2 S1 N1 107.28(9) . .
O1 S1 N1 107.06(9) . .
O2 S1 C1 107.12(8) . .
O1 S1 C1 108.03(8) . .
N1 S1 C1 107.63(8) . .
C15 O8 C19 117.54(17) . .
C6 C1 C2 121.28(17) . .
C6 C1 S1 120.03(13) . .
C2 C1 S1 118.65(13) . .
C14 N3 C18 124.42(16) . .
C3 C4 C5 119.66(17) . .
C3 C4 C7 121.49(16) . .
C5 C4 C7 118.85(16) . .
C1 C6 C5 118.96(17) . .
C4 C3 C2 120.58(17) . .
O8 C15 C16 127.23(17) . .
O8 C15 C14 112.34(16) . .
C16 C15 C14 120.43(18) . .
O3 C7 O4 124.14(17) . .
O3 C7 C4 121.82(17) . .
O4 C7 C4 114.04(16) . .
O7 C14 N3 121.46(16) . .
O7 C14 C15 123.06(17) . .
N3 C14 C15 115.48(16) . .
C6 C5 C4 120.60(18) . .
C1 C2 C3 118.90(17) . .
C15 C16 C17 120.19(18) . .
C17 C18 N3 119.9(2) . .
C18 C17 C16 119.6(2) . .
C8 N2 C12 125.10(17) . .
C9 O6 C13 117.14(16) . .
C11 C12 N2 119.34(19) . .
O6 C9 C10 127.36(18) . .
O6 C9 C8 112.37(17) . .
C10 C9 C8 120.27(18) . .
C9 C10 C11 120.40(19) . .
O5 C8 N2 121.80(17) . .
O5 C8 C9 122.80(17) . .
N2 C8 C9 115.39(17) . .
C12 C11 C10 119.4(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.4263(13) .
S1 O1 1.4305(13) .
S1 N1 1.6031(16) .
S1 C1 1.7788(18) .
O7 C14 1.248(2) .
O8 C15 1.346(2) .
O8 C19 1.420(2) .
C1 C6 1.376(2) .
C1 C2 1.379(2) .
N3 C14 1.352(2) .
N3 C18 1.361(3) .
O4 C7 1.311(2) .
C4 C3 1.375(3) .
C4 C5 1.379(3) .
C4 C7 1.495(2) .
O3 C7 1.211(2) .
C6 C5 1.379(3) .
C3 C2 1.382(3) .
C15 C16 1.356(3) .
C15 C14 1.441(2) .
C16 C17 1.404(3) .
C18 C17 1.339(3) .
O5 C8 1.252(2) .
N2 C8 1.350(2) .
N2 C12 1.365(3) .
O6 C9 1.351(2) .
O6 C13 1.425(2) .
C12 C11 1.343(3) .
C9 C10 1.355(3) .
C9 C8 1.446(3) .
C10 C11 1.415(3) .
