#------------------------------------------------------------------------------
#$Date: 2015-10-20 17:01:13 +0300 (Tue, 20 Oct 2015) $
#$Revision: 169191 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/79/7117961.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_7117961
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         2(C7H7NO4S),C6H6N2O,2(C6H7NO2)
_chemical_formula_sum            'C32 H34 N6 O13 S2'
_chemical_formula_weight         774.77
_chemical_melting_point          431
_chemical_name_common
'Sulfonamide benzoic acid; nicotinamide; 3methoxy 2pyridone'
_chemical_name_systematic
'Sulfonamide benzoic acid; nicotinamide; 3methoxy 2pyridone'
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 91.962(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2514(3)
_cell_length_b                   7.05170(19)
_cell_length_c                   38.1412(9)
_cell_measurement_reflns_used    4131
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      71.5320
_cell_measurement_theta_min      4.1310
_cell_volume                     3562.01(15)
_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  '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  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            6038
_diffrn_reflns_theta_full        65.05
_diffrn_reflns_theta_max         65.05
_diffrn_reflns_theta_min         4.64
_exptl_absorpt_coefficient_mu    2.002
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60744
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLORLES
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             1616
_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         0.200
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.040(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         3639
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0320
_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)+(0.0624P)²+0.3910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0857
_reflns_number_gt                3595
_reflns_number_total             3639
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc06475a2.cif
_cod_data_source_block           SMBANAMOMEHP212
_cod_original_cell_volume        3562.02(15)
_cod_database_code               7117961
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'
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 0.31326(4) 0.14902(9) 0.210850(17) 0.03829(16) Uani 1 1 d . . .
O15 O 0.44885(18) 0.6254(3) 0.26090(6) 0.0505(5) Uani 1 1 d . . .
C22 C 0.4219(2) 0.6873(4) 0.29278(8) 0.0409(6) Uani 1 1 d . . .
N2 N 0.4054(2) 0.2385(4) 0.23312(7) 0.0439(5) Uani 1 1 d . . .
O5 O 0.25363(19) 0.0449(3) 0.23461(6) 0.0554(5) Uani 1 1 d . . .
O7 O 0.01902(16) 0.9017(3) 0.17296(6) 0.0504(5) Uani 1 1 d . . .
O6 O 0.35376(18) 0.0504(3) 0.18160(6) 0.0537(5) Uani 1 1 d . . .
N3 N 0.3294(2) 0.6059(3) 0.34277(6) 0.0426(5) Uani 1 1 d . . .
H3A H 0.2912 0.5296 0.3538 0.051 Uiso 1 1 calc R . .
C5 C 0.1221(2) 0.4482(4) 0.14828(7) 0.0431(6) Uani 1 1 d . . .
H5 H 0.0874 0.4314 0.1269 0.052 Uiso 1 1 calc R . .
O14 O 0.32958(18) 0.3993(3) 0.29711(6) 0.0527(5) Uani 1 1 d . . .
C7 C 0.0396(2) 0.7665(4) 0.15443(7) 0.0406(6) Uani 1 1 d . . .
C21 C 0.3578(2) 0.5530(4) 0.31024(7) 0.0405(6) Uani 1 1 d . . .
C2 C 0.2259(2) 0.5009(4) 0.21208(7) 0.0413(6) Uani 1 1 d . . .
H2 H 0.2611 0.5180 0.2334 0.050 Uiso 1 1 calc R . .
O8 O 0.00272(17) 0.7422(3) 0.12262(5) 0.0517(5) Uani 1 1 d . . .
H23 H -0.0371 0.8279 0.1177 0.078 Uiso 1 1 calc R . .
C1 C 0.23662(19) 0.3354(4) 0.19306(7) 0.0358(5) Uani 1 1 d . . .
C6 C 0.1857(2) 0.3080(4) 0.16132(7) 0.0426(6) Uani 1 1 d . . .
H6 H 0.1941 0.1962 0.1488 0.051 Uiso 1 1 calc R . .
C4 C 0.1099(2) 0.6142(4) 0.16718(7) 0.0365(5) Uani 1 1 d . . .
C26 C 0.5158(3) 0.7436(5) 0.24206(9) 0.0556(8) Uani 1 1 d . . .
H26A H 0.4849 0.8649 0.2379 0.083 Uiso 1 1 calc R . .
H26B H 0.5300 0.6851 0.2200 0.083 Uiso 1 1 calc R . .
H26C H 0.5776 0.7600 0.2556 0.083 Uiso 1 1 calc R . .
C23 C 0.4488(3) 0.8519(4) 0.30850(9) 0.0543(8) Uani 1 1 d . . .
H23A H 0.4890 0.9378 0.2968 0.065 Uiso 1 1 calc R . .
C3 C 0.1621(2) 0.6401(4) 0.19887(8) 0.0422(6) Uani 1 1 d . . .
H3 H 0.1540 0.7520 0.2114 0.051 Uiso 1 1 calc R . .
C24 C 0.4164(3) 0.8951(5) 0.34253(11) 0.0615(9) Uani 1 1 d . . .
H24 H 0.4359 1.0080 0.3534 0.074 Uiso 1 1 calc R . .
C25 C 0.3570(2) 0.7707(5) 0.35911(9) 0.0538(8) Uani 1 1 d . . .
H25 H 0.3351 0.7973 0.3815 0.065 Uiso 1 1 calc R . .
S2 S 0.70388(5) 1.11056(11) 0.45749(2) 0.04745(18) Uani 1 1 d . . .
O17 O 0.07515(19) 0.1193(4) 0.40957(7) 0.0603(6) Uani 1 1 d . . .
N6 N 0.1926(2) 0.1392(4) 0.32777(7) 0.0465(6) Uani 1 1 d . . .
O9 O 0.6641(2) 1.2212(4) 0.48498(7) 0.0656(6) Uani 1 1 d . . .
C27 C 0.1650(2) 0.1927(4) 0.36001(8) 0.0428(6) Uani 1 1 d . . .
C28 C 0.1003(2) 0.0592(5) 0.37747(8) 0.0481(7) Uani 1 1 d . . .
C8 C 0.7846(2) 0.9380(4) 0.47728(7) 0.0433(6) Uani 1 1 d . . .
O12 O 1.00832(19) 0.3962(3) 0.51212(7) 0.0577(6) Uani 1 1 d . . .
N1 N 0.6123(3) 1.0056(5) 0.43770(9) 0.0590(7) Uani 1 1 d . . .
C11 C 0.9187(2) 0.6877(4) 0.50937(8) 0.0429(6) Uani 1 1 d . . .
C12 C 0.9099(2) 0.8698(4) 0.52177(8) 0.0451(6) Uani 1 1 d . . .
H12 H 0.9493 0.9078 0.5412 0.054 Uiso 1 1 calc R . .
C9 C 0.7913(2) 0.7559(5) 0.46462(8) 0.0501(7) Uani 1 1 d . . .
H9 H 0.7512 0.7175 0.4454 0.060 Uiso 1 1 calc R . .
O10 O 0.7608(2) 1.2063(4) 0.43166(7) 0.0708(7) Uani 1 1 d . . .
C10 C 0.8588(3) 0.6297(5) 0.48088(9) 0.0534(8) Uani 1 1 d . . .
H10 H 0.8638 0.5062 0.4726 0.064 Uiso 1 1 calc R . .
C32 C 0.0079(3) 0.0038(7) 0.42864(11) 0.0732(11) Uani 1 1 d . . .
H32A H -0.0577 0.0050 0.4171 0.110 Uiso 1 1 calc R . .
H32B H 0.0030 0.0526 0.4520 0.110 Uiso 1 1 calc R . .
H32C H 0.0330 -0.1238 0.4296 0.110 Uiso 1 1 calc R . .
C13 C 0.8437(2) 0.9978(4) 0.50589(8) 0.0467(6) Uani 1 1 d . . .
H13 H 0.8389 1.1212 0.5142 0.056 Uiso 1 1 calc R . .
C14 C 0.9920(2) 0.5589(5) 0.52832(8) 0.0471(7) Uani 1 1 d . . .
O11 O 1.03167(19) 0.6034(4) 0.55615(6) 0.0608(6) Uani 1 1 d . . .
C29 C 0.0724(3) -0.1026(5) 0.36174(10) 0.0596(8) Uani 1 1 d . . .
H29 H 0.0315 -0.1876 0.3733 0.072 Uiso 1 1 calc R . .
C30 C 0.1043(3) -0.1462(5) 0.32772(11) 0.0663(10) Uani 1 1 d . . .
H30 H 0.0838 -0.2582 0.3167 0.080 Uiso 1 1 calc R . .
C31 C 0.1645(3) -0.0240(5) 0.31145(9) 0.0527(7) Uani 1 1 d . . .
H31 H 0.1869 -0.0512 0.2891 0.063 Uiso 1 1 calc R . .
O13 O 0.36331(16) 0.4746(3) 0.10197(5) 0.0493(5) Uani 1 1 d . . .
N5 N 0.14879(18) 0.7985(4) 0.04914(7) 0.0442(5) Uani 1 1 d . . .
C16 C 0.2076(2) 0.6932(4) 0.07080(7) 0.0400(6) Uani 1 1 d . . .
H16 H 0.1977 0.5627 0.0710 0.048 Uiso 1 1 calc R . .
C15 C 0.2818(2) 0.7682(4) 0.09261(7) 0.0360(5) Uani 1 1 d . . .
C19 C 0.2973(2) 0.9635(4) 0.09248(8) 0.0453(6) Uani 1 1 d . . .
H19 H 0.3466 1.0190 0.1071 0.054 Uiso 1 1 calc R . .
N4 N 0.3893(2) 0.6973(4) 0.14330(7) 0.0501(6) Uani 1 1 d . . .
H4A H 0.4283 0.6239 0.1556 0.060 Uiso 1 1 calc R . .
H4B H 0.3772 0.8104 0.1505 0.060 Uiso 1 1 calc R . .
C20 C 0.3481(2) 0.6363(4) 0.11335(7) 0.0380(6) Uani 1 1 d . . .
C18 C 0.2376(3) 1.0721(4) 0.07012(9) 0.0525(7) Uani 1 1 d . . .
H18 H 0.2458 1.2030 0.0694 0.063 Uiso 1 1 calc R . .
C17 C 0.1657(2) 0.9848(4) 0.04884(8) 0.0485(7) Uani 1 1 d . . .
H17 H 0.1270 1.0596 0.0335 0.058 Uiso 1 1 calc R . .
H6A H 0.232(3) 0.214(6) 0.3191(10) 0.054(10) Uiso 1 1 d . . .
O16 O 0.19394(19) 0.3443(4) 0.37360(6) 0.0614(6) Uani 1 1 d . . .
H2A H 0.437(3) 0.301(5) 0.2216(9) 0.038(9) Uiso 1 1 d . . .
H1A H 0.625(3) 0.944(6) 0.4205(10) 0.049(10) Uiso 1 1 d . . .
H2B H 0.388(3) 0.287(6) 0.2527(11) 0.059(11) Uiso 1 1 d . . .
H1B H 0.571(5) 0.947(9) 0.4473(18) 0.12(2) Uiso 1 1 d . . .
H1C H 1.057(5) 0.323(10) 0.5239(17) 0.15(3) 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
O5 S1 O6 118.36(13) . .
O5 S1 N2 107.24(15) . .
O6 S1 N2 107.82(14) . .
O5 S1 C1 107.50(13) . .
O6 S1 C1 106.56(13) . .
N2 S1 C1 109.12(13) . .
C22 O15 C26 116.9(2) . .
C23 C22 O15 127.1(3) . .
C23 C22 C21 120.6(3) . .
O15 C22 C21 112.3(2) . .
C21 N3 C25 124.9(3) . .
C6 C5 C4 119.8(3) . .
O7 C7 O8 123.8(3) . .
O7 C7 C4 121.4(3) . .
O8 C7 C4 114.7(2) . .
O14 C21 N3 121.1(3) . .
O14 C21 C22 123.8(3) . .
N3 C21 C22 115.1(2) . .
C3 C2 C1 118.8(2) . .
C6 C1 C2 121.5(2) . .
C6 C1 S1 119.1(2) . .
C2 C1 S1 119.3(2) . .
C1 C6 C5 119.4(2) . .
C3 C4 C5 120.1(3) . .
C3 C4 C7 118.5(2) . .
C5 C4 C7 121.3(2) . .
C22 C23 C24 120.6(3) . .
C2 C3 C4 120.4(2) . .
C25 C24 C23 119.4(3) . .
C24 C25 N3 119.4(3) . .
O9 S2 O10 117.79(17) . .
O9 S2 N1 108.03(17) . .
O10 S2 N1 107.73(19) . .
O9 S2 C8 107.24(15) . .
O10 S2 C8 107.01(15) . .
N1 S2 C8 108.79(16) . .
C28 O17 C32 117.6(3) . .
C27 N6 C31 125.3(3) . .
O16 C27 N6 122.1(3) . .
O16 C27 C28 123.0(3) . .
N6 C27 C28 114.9(3) . .
C29 C28 O17 127.1(3) . .
C29 C28 C27 120.5(3) . .
O17 C28 C27 112.4(3) . .
C9 C8 C13 121.2(3) . .
C9 C8 S2 122.5(2) . .
C13 C8 S2 116.3(2) . .
C12 C11 C10 119.5(3) . .
C12 C11 C14 117.5(3) . .
C10 C11 C14 123.0(3) . .
C11 C12 C13 121.2(3) . .
C8 C9 C10 119.2(3) . .
C11 C10 C9 120.2(3) . .
C12 C13 C8 118.6(3) . .
O11 C14 O12 124.1(3) . .
O11 C14 C11 121.4(3) . .
O12 C14 C11 114.5(3) . .
C28 C29 C30 120.8(3) . .
C31 C30 C29 119.1(3) . .
C30 C31 N6 119.5(3) . .
C17 N5 C16 117.2(3) . .
N5 C16 C15 123.3(3) . .
C16 C15 C19 118.8(3) . .
C16 C15 C20 118.6(2) . .
C19 C15 C20 122.4(2) . .
C18 C19 C15 118.1(3) . .
O13 C20 N4 122.3(3) . .
O13 C20 C15 119.3(2) . .
N4 C20 C15 118.4(2) . .
C19 C18 C17 119.2(3) . .
N5 C17 C18 123.3(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O5 1.426(2) .
S1 O6 1.434(2) .
S1 N2 1.594(3) .
S1 C1 1.781(3) .
O15 C22 1.352(4) .
O15 C26 1.429(4) .
C22 C23 1.349(4) .
C22 C21 1.449(4) .
O7 C7 1.222(4) .
N3 C21 1.361(4) .
N3 C25 1.363(4) .
C5 C6 1.381(4) .
C5 C4 1.387(4) .
O14 C21 1.246(4) .
C7 O8 1.304(3) .
C7 C4 1.493(4) .
C2 C3 1.380(4) .
C2 C1 1.384(4) .
C1 C6 1.380(4) .
C4 C3 1.384(4) .
C23 C24 1.414(5) .
C24 C25 1.350(5) .
S2 O9 1.423(2) .
S2 O10 1.430(3) .
S2 N1 1.590(4) .
S2 C8 1.772(3) .
O17 C28 1.348(4) .
O17 C32 1.425(4) .
N6 C27 1.348(4) .
N6 C31 1.355(4) .
C27 O16 1.243(4) .
C27 C28 1.450(4) .
C28 C29 1.335(5) .
C8 C9 1.376(4) .
C8 C13 1.387(4) .
O12 C14 1.324(4) .
C11 C12 1.375(4) .
C11 C10 1.385(4) .
C11 C14 1.497(4) .
C12 C13 1.384(4) .
C9 C10 1.393(5) .
C14 O11 1.210(4) .
C29 C30 1.413(6) .
C30 C31 1.341(5) .
O13 C20 1.239(3) .
N5 C17 1.333(4) .
N5 C16 1.341(4) .
C16 C15 1.371(4) .
C15 C19 1.393(4) .
C15 C20 1.489(4) .
C19 C18 1.376(4) .
N4 C20 1.321(4) .
C18 C17 1.376(5) .
