#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/79/7117959.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_7117959
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,C5H5NO
_chemical_formula_sum            'C18 H18 N4 O6 S'
_chemical_formula_weight         418.42
_chemical_melting_point          413
_chemical_name_common
'Sulfonamide benzoic acid; nicotinamide; 2pyridone'
_chemical_name_systematic
'Sulfonamide benzoic acid; nicotinamide; 2pyridone'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 117.924(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.7594(7)
_cell_length_b                   5.25798(10)
_cell_length_c                   20.2747(7)
_cell_measurement_reflns_used    5510
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      71.6440
_cell_measurement_theta_min      4.3100
_cell_volume                     1861.18(12)
_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  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11494
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.94
_exptl_absorpt_coefficient_mu    1.959
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72572
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLORLES
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             872
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOAC, THF'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.045
_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     269
_refine_ls_number_reflns         3327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0406
_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)+(0.0661P)²+0.7522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                2966
_reflns_number_total             3327
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc06475a2.cif
_cod_data_source_block           SMBANAMHP111
_cod_original_cell_volume        1861.18(10)
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               7117959
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C2 C 0.96512(12) 0.4163(4) 0.09383(12) 0.0490(5) Uani 1 1 d . . .
H2 H 0.9779 0.5253 0.0653 0.059 Uiso 1 1 calc R . .
C5 C 0.92598(12) 0.0855(4) 0.17678(12) 0.0475(5) Uani 1 1 d . . .
H5 H 0.9122 -0.0282 0.2036 0.057 Uiso 1 1 calc R . .
C3 C 0.89995(11) 0.4581(4) 0.10123(12) 0.0472(5) Uani 1 1 d . . .
H3 H 0.8689 0.5973 0.0778 0.057 Uiso 1 1 calc R . .
C6 C 0.99179(12) 0.0444(4) 0.17066(12) 0.0466(5) Uani 1 1 d . . .
H6 H 1.0230 -0.0943 0.1942 0.056 Uiso 1 1 calc R . .
C1 C 1.01084(11) 0.2107(4) 0.12941(11) 0.0405(4) Uani 1 1 d . . .
C4 C 0.88038(11) 0.2948(4) 0.14326(10) 0.0401(4) Uani 1 1 d . . .
S1 S 1.09788(3) 0.16577(10) 0.12535(3) 0.04658(18) Uani 1 1 d . . .
O5 O 0.45914(8) 1.1634(3) 0.14178(8) 0.0459(3) Uani 1 1 d . . .
O6 O 0.40197(9) 0.6915(3) 0.01142(9) 0.0526(4) Uani 1 1 d . . .
N2 N 0.34773(9) 0.5540(3) 0.08128(9) 0.0428(4) Uani 1 1 d . . .
H2A H 0.3812 0.4341 0.0985 0.051 Uiso 1 1 calc R . .
N3 N 0.66929(9) 0.6641(3) 0.16372(10) 0.0451(4) Uani 1 1 d . . .
N4 N 0.50751(9) 1.2568(3) 0.06434(9) 0.0445(4) Uani 1 1 d . . .
H4A H 0.4755 1.3793 0.0441 0.053 Uiso 1 1 calc R . .
H4B H 0.5407 1.2224 0.0494 0.053 Uiso 1 1 calc R . .
O4 O 0.78068(9) 0.5647(3) 0.13104(11) 0.0632(5) Uani 1 1 d . . .
H4C H 0.7430 0.5800 0.1376 0.095 Uiso 1 1 calc R . .
O3 O 0.78712(9) 0.1826(3) 0.18119(10) 0.0627(4) Uani 1 1 d . . .
C13 C 0.50566(10) 1.1215(4) 0.11840(10) 0.0361(4) Uani 1 1 d . . .
C12 C 0.61885(11) 0.8531(4) 0.13253(11) 0.0419(4) Uani 1 1 d . . .
H12 H 0.6216 0.9502 0.0955 0.050 Uiso 1 1 calc R . .
C11 C 0.66573(11) 0.5272(4) 0.21757(11) 0.0456(5) Uani 1 1 d . . .
H11 H 0.7006 0.3955 0.2394 0.055 Uiso 1 1 calc R . .
C8 C 0.56290(10) 0.9103(4) 0.15291(10) 0.0359(4) Uani 1 1 d . . .
O2 O 1.08606(11) 0.2343(4) 0.05319(10) 0.0730(5) Uani 1 1 d . . .
C15 C 0.29747(12) 0.9239(4) 0.00898(12) 0.0473(5) Uani 1 1 d . . .
H15 H 0.2986 1.0493 -0.0228 0.057 Uiso 1 1 calc R . .
C9 C 0.56050(11) 0.7666(4) 0.20905(11) 0.0422(4) Uani 1 1 d . . .
H9 H 0.5239 0.8005 0.2245 0.051 Uiso 1 1 calc R . .
C14 C 0.35225(10) 0.7224(4) 0.03217(10) 0.0398(4) Uani 1 1 d . . .
C7 C 0.81112(11) 0.3406(4) 0.15386(11) 0.0445(5) Uani 1 1 d . . .
C17 C 0.24118(12) 0.7510(5) 0.08114(13) 0.0531(5) Uani 1 1 d . . .
H17 H 0.2038 0.7580 0.0967 0.064 Uiso 1 1 calc R . .
O1 O 1.12539(10) -0.0815(3) 0.15425(12) 0.0707(5) Uani 1 1 d . . .
N1 N 1.15996(12) 0.3632(5) 0.18284(14) 0.0613(5) Uani 1 1 d . . .
H1A H 1.1451(17) 0.515(6) 0.1669(16) 0.074 Uiso 1 1 d . . .
H1B H 1.1708(17) 0.322(6) 0.2245(17) 0.074 Uiso 1 1 d . . .
C10 C 0.61276(12) 0.5732(4) 0.24187(11) 0.0468(5) Uani 1 1 d . . .
H10 H 0.6121 0.4756 0.2798 0.056 Uiso 1 1 calc R . .
C18 C 0.29351(12) 0.5646(4) 0.10462(12) 0.0494(5) Uani 1 1 d . . .
H18 H 0.2928 0.4414 0.1372 0.059 Uiso 1 1 calc R . .
C16 C 0.24398(12) 0.9347(4) 0.03270(12) 0.0505(5) Uani 1 1 d . . .
H16 H 0.2085 1.0665 0.0165 0.061 Uiso 1 1 calc R . .
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
C1 C2 C3 118.97(19) . .
C6 C5 C4 120.34(19) . .
C2 C3 C4 120.68(18) . .
C1 C6 C5 119.46(18) . .
C2 C1 C6 121.16(18) . .
C2 C1 S1 119.50(15) . .
C6 C1 S1 119.29(15) . .
C5 C4 C3 119.35(18) . .
C5 C4 C7 119.05(18) . .
C3 C4 C7 121.60(18) . .
O2 S1 O1 120.24(12) . .
O2 S1 N1 106.54(13) . .
O1 S1 N1 105.99(12) . .
O2 S1 C1 108.62(10) . .
O1 S1 C1 107.07(10) . .
N1 S1 C1 107.82(10) . .
C18 N2 C14 123.91(17) . .
C11 N3 C12 118.27(16) . .
O5 C13 N4 122.46(17) . .
O5 C13 C8 119.07(16) . .
N4 C13 C8 118.46(15) . .
N3 C12 C8 122.90(18) . .
N3 C11 C10 122.66(18) . .
C12 C8 C9 117.83(17) . .
C12 C8 C13 123.66(16) . .
C9 C8 C13 118.50(16) . .
C16 C15 C14 120.84(19) . .
C10 C9 C8 119.54(17) . .
O6 C14 N2 119.48(17) . .
O6 C14 C15 125.53(18) . .
N2 C14 C15 114.99(17) . .
O3 C7 O4 124.54(19) . .
O3 C7 C4 122.26(19) . .
O4 C7 C4 113.20(18) . .
C18 C17 C16 118.52(19) . .
C11 C10 C9 118.80(18) . .
C17 C18 N2 120.6(2) . .
C15 C16 C17 121.07(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 C1 1.376(3) .
C2 C3 1.382(3) .
C5 C6 1.380(3) .
C5 C4 1.382(3) .
C3 C4 1.386(3) .
C6 C1 1.378(3) .
C1 S1 1.7759(19) .
C4 C7 1.501(3) .
S1 O2 1.4157(17) .
S1 O1 1.4250(16) .
S1 N1 1.613(2) .
O5 C13 1.235(2) .
O6 C14 1.247(2) .
N2 C18 1.360(2) .
N2 C14 1.366(2) .
N3 C11 1.337(3) .
N3 C12 1.338(3) .
N4 C13 1.321(2) .
O4 C7 1.306(3) .
O3 C7 1.212(3) .
C13 C8 1.504(3) .
C12 C8 1.382(2) .
C11 C10 1.371(3) .
C8 C9 1.385(3) .
C15 C16 1.352(3) .
C15 C14 1.428(3) .
C9 C10 1.379(3) .
C17 C18 1.340(3) .
C17 C16 1.397(3) .
