#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/79/7117954.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_7117954
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,C5H5NO
_chemical_formula_sum            'C12 H12 N2 O5 S'
_chemical_formula_weight         296.30
_chemical_melting_point          409
_chemical_name_common
'Sulfonamide benzoic acid; 2pyridone form III'
_chemical_name_systematic
'Sulfonamide benzoic acid; 2pyridone form III'
_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                 100.001(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.464(3)
_cell_length_b                   9.721(3)
_cell_length_c                   16.137(5)
_cell_measurement_reflns_used    5511
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      2.44
_cell_volume                     1307.6(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13109
_diffrn_reflns_theta_full        26.47
_diffrn_reflns_theta_max         26.47
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLES
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             616
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOAc, THF'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.098
_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     197
_refine_ls_number_reflns         2686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0926P)²+0.1962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1438
_reflns_number_gt                2223
_reflns_number_total             2686
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc06475a2.cif
_cod_data_source_block           SMBAHPFORMIII
_cod_original_cell_volume        1307.5(7)
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               7117954
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 0.18387(6) 0.58217(5) 0.25936(3) 0.0407(2) Uani 1 1 d . . .
O3 O 0.12238(19) 0.65526(18) -0.16234(9) 0.0615(5) Uani 1 1 d . . .
O1 O 0.05040(18) 0.66155(18) 0.27475(10) 0.0595(4) Uani 1 1 d . . .
C4 C 0.2003(2) 0.58423(19) -0.01994(12) 0.0400(4) Uani 1 1 d . . .
C1 C 0.1846(2) 0.58158(18) 0.14937(12) 0.0375(4) Uani 1 1 d . . .
O5 O 0.37142(19) 0.50044(18) 0.71909(10) 0.0602(5) Uani 1 1 d . . .
O2 O 0.1994(2) 0.44225(16) 0.28715(10) 0.0534(4) Uani 1 1 d . . .
C2 C 0.0878(2) 0.6702(2) 0.09667(13) 0.0457(5) Uani 1 1 d . . .
H2 H 0.0184 0.7292 0.1181 0.055 Uiso 1 1 calc R . .
C7 C 0.2085(2) 0.5861(2) -0.11220(13) 0.0442(5) Uani 1 1 d . . .
O4 O 0.3178(2) 0.5035(2) -0.13106(11) 0.0795(7) Uani 1 1 d . . .
C6 C 0.2889(2) 0.4929(2) 0.11894(12) 0.0432(5) Uani 1 1 d . . .
H6 H 0.3527 0.4325 0.1550 0.052 Uiso 1 1 calc R . .
N1 N 0.3446(2) 0.6597(2) 0.30314(11) 0.0483(4) Uani 1 1 d . . .
N2 N 0.1520(2) 0.6235(2) 0.66115(13) 0.0567(5) Uani 1 1 d . . .
C5 C 0.2967(2) 0.4956(2) 0.03391(12) 0.0447(5) Uani 1 1 d . . .
H5 H 0.3674 0.4373 0.0128 0.054 Uiso 1 1 calc R . .
C3 C 0.0945(2) 0.6711(2) 0.01146(13) 0.0451(5) Uani 1 1 d . . .
H3 H 0.0282 0.7297 -0.0246 0.054 Uiso 1 1 calc R . .
C8 C 0.2850(3) 0.5492(2) 0.65493(13) 0.0484(5) Uani 1 1 d . . .
C9 C 0.3154(3) 0.5334(3) 0.57146(15) 0.0621(6) Uani 1 1 d . . .
H9 H 0.4058 0.4853 0.5623 0.075 Uiso 1 1 calc R . .
C10 C 0.2147(4) 0.5875(3) 0.50543(16) 0.0692(7) Uani 1 1 d . . .
H10 H 0.2368 0.5753 0.4514 0.083 Uiso 1 1 calc R . .
C11 C 0.0783(3) 0.6612(3) 0.51623(16) 0.0651(7) Uani 1 1 d . . .
H11 H 0.0088 0.6977 0.4705 0.078 Uiso 1 1 calc R . .
C12 C 0.0515(3) 0.6774(3) 0.59548(16) 0.0655(7) Uani 1 1 d . . .
H12 H -0.0379 0.7266 0.6050 0.079 Uiso 1 1 calc R . .
H1A H 0.340(3) 0.749(3) 0.2913(18) 0.075(9) Uiso 1 1 d . . .
H2A H 0.144(4) 0.638(3) 0.710(2) 0.084(10) Uiso 1 1 d . . .
H4A H 0.333(4) 0.512(3) -0.180(2) 0.086(10) Uiso 1 1 d . . .
H1B H 0.424(3) 0.608(3) 0.2969(17) 0.064(8) 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
O1 S1 O2 119.52(10) . .
O1 S1 N1 107.78(11) . .
O2 S1 N1 106.45(11) . .
O1 S1 C1 108.45(9) . .
O2 S1 C1 107.10(9) . .
N1 S1 C1 106.92(9) . .
C5 C4 C3 119.77(18) . .
C5 C4 C7 120.40(17) . .
C3 C4 C7 119.83(17) . .
C2 C1 C6 121.25(18) . .
C2 C1 S1 120.69(15) . .
C6 C1 S1 118.03(14) . .
C1 C2 C3 119.64(18) . .
O3 C7 O4 124.27(19) . .
O3 C7 C4 123.32(18) . .
O4 C7 C4 112.41(17) . .
C1 C6 C5 118.88(17) . .
C12 N2 C8 124.7(2) . .
C4 C5 C6 120.59(17) . .
C2 C3 C4 119.86(18) . .
O5 C8 N2 120.89(19) . .
O5 C8 C9 124.5(2) . .
N2 C8 C9 114.6(2) . .
C10 C9 C8 120.8(3) . .
C9 C10 C11 121.6(2) . .
C12 C11 C10 117.3(2) . .
N2 C12 C11 121.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.4251(16) .
S1 O2 1.4311(17) .
S1 N1 1.6073(19) .
S1 C1 1.776(2) .
O3 C7 1.197(2) .
C4 C5 1.385(3) .
C4 C3 1.389(3) .
C4 C7 1.503(3) .
C1 C2 1.376(3) .
C1 C6 1.384(3) .
O5 C8 1.252(3) .
C2 C3 1.386(3) .
C7 O4 1.301(3) .
C6 C5 1.385(3) .
N2 C12 1.345(3) .
N2 C8 1.356(3) .
C8 C9 1.423(3) .
C9 C10 1.350(4) .
C10 C11 1.395(4) .
C11 C12 1.346(4) .
