#------------------------------------------------------------------------------
#$Date: 2015-10-20 17:01:13 +0300 (Tue, 20 Oct 2015) $
#$Revision: 169191 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/79/7117958.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_7117958
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(C6H6 N2O)'
_chemical_formula_sum            'C19 H18 N5 O6 S'
_chemical_formula_weight         444.44
_chemical_melting_point          403
_chemical_name_common            'Sulfonamide benzoic acid; nicotinamide'
_chemical_name_systematic        'Sulfonamide benzoic acid; nicotinamide'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                95.966(12)
_cell_angle_beta                 90.050(9)
_cell_angle_gamma                95.469(10)
_cell_formula_units_Z            2
_cell_length_a                   5.0179(5)
_cell_length_b                   11.3168(17)
_cell_length_c                   18.156(2)
_cell_measurement_reflns_used    1536
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.8140
_cell_measurement_theta_min      4.2240
_cell_volume                     1020.7(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7085
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94686
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLORLES
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             462
_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         0.535
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0577
_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)+(0.0533P)²+0.0885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1482
_reflns_number_gt                2562
_reflns_number_total             4153
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc06475a2.cif
_cod_data_source_block           SMBANAM12
_cod_database_code               7117958
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.34677(16) 0.35347(9) 1.09212(5) 0.0568(3) Uani 1 1 d . . .
O5 O -0.3834(4) 0.87336(17) 0.53790(11) 0.0442(5) Uani 1 1 d . . .
O1 O -0.3293(4) 0.1006(2) 0.79023(12) 0.0554(6) Uani 1 1 d . . .
N3 N -0.2406(5) 1.0644(2) 0.57098(16) 0.0431(6) Uani 1 1 d . . .
N2 N 0.3397(4) 0.9495(2) 0.70997(13) 0.0427(6) Uani 1 1 d . . .
O2 O -0.1782(5) -0.0592(2) 0.82906(13) 0.0658(7) Uani 1 1 d . . .
C19 C -0.2326(5) 0.9488(2) 0.57536(15) 0.0339(6) Uani 1 1 d . . .
C15 C 0.1627(5) 0.9861(3) 0.66478(15) 0.0388(7) Uani 1 1 d . . .
H15 H 0.1715 1.0669 0.6586 0.047 Uiso 1 1 calc R . .
C14 C -0.0334(5) 0.9096(2) 0.62665(14) 0.0330(6) Uani 1 1 d . . .
N1 N 0.1545(5) 0.3147(3) 1.15748(14) 0.0508(7) Uani 1 1 d . . .
H1A H -0.003(6) 0.332(3) 1.1524(17) 0.061 Uiso 1 1 d . . .
H1B H 0.175(6) 0.234(3) 1.1627(18) 0.061 Uiso 1 1 d . . .
C18 C -0.0429(5) 0.7900(3) 0.63662(16) 0.0408(7) Uani 1 1 d . . .
H18 H -0.1728 0.7358 0.6121 0.049 Uiso 1 1 calc R . .
C1 C 0.2188(6) 0.2696(3) 1.00998(16) 0.0478(8) Uani 1 1 d . . .
C7 C -0.1861(6) 0.0472(3) 0.83388(16) 0.0438(7) Uani 1 1 d . . .
C16 C 0.3267(6) 0.8334(3) 0.71883(16) 0.0451(7) Uani 1 1 d . . .
H16 H 0.4489 0.8075 0.7506 0.054 Uiso 1 1 calc R . .
C4 C -0.0335(5) 0.1287(3) 0.89251(15) 0.0412(7) Uani 1 1 d . . .
C17 C 0.1399(6) 0.7512(3) 0.68277(17) 0.0461(7) Uani 1 1 d . . .
H17 H 0.1370 0.6707 0.6894 0.055 Uiso 1 1 calc R . .
C5 C -0.0921(6) 0.2451(3) 0.90912(16) 0.0487(8) Uani 1 1 d . . .
H5 H -0.2164 0.2763 0.8804 0.058 Uiso 1 1 calc R . .
O4 O 0.5996(4) 0.3142(3) 1.10828(14) 0.0858(9) Uani 1 1 d . . .
C3 C 0.1586(6) 0.0849(3) 0.93380(17) 0.0547(9) Uani 1 1 d . . .
H3 H 0.2026 0.0072 0.9218 0.066 Uiso 1 1 calc R . .
C6 C 0.0332(6) 0.3154(3) 0.96814(17) 0.0536(8) Uani 1 1 d . . .
H6 H -0.0080 0.3935 0.9796 0.064 Uiso 1 1 calc R . .
C2 C 0.2857(6) 0.1545(3) 0.99249(18) 0.0587(9) Uani 1 1 d . . .
H2 H 0.4152 0.1245 1.0201 0.070 Uiso 1 1 calc R . .
O6 O 0.1436(4) 0.47347(18) 0.41162(12) 0.0560(6) Uani 1 1 d . . .
N4 N 0.9084(5) 0.7235(2) 0.34940(14) 0.0467(6) Uani 1 1 d . . .
C8 C 0.5131(5) 0.5989(2) 0.37731(15) 0.0371(7) Uani 1 1 d . . .
N5 N 0.2944(5) 0.6232(2) 0.49642(14) 0.0483(7) Uani 1 1 d . . .
H5A H 0.1744 0.6026 0.5276 0.058 Uiso 1 1 calc R . .
H5B H 0.4085 0.6839 0.5080 0.058 Uiso 1 1 calc R . .
C13 C 0.3035(5) 0.5608(2) 0.43004(16) 0.0403(7) Uani 1 1 d . . .
C9 C 0.7229(5) 0.6858(2) 0.39616(16) 0.0414(7) Uani 1 1 d . . .
H9 H 0.7348 0.7202 0.4450 0.050 Uiso 1 1 calc R . .
C10 C 0.8899(6) 0.6729(3) 0.28048(18) 0.0528(8) Uani 1 1 d . . .
H10 H 1.0172 0.6978 0.2467 0.063 Uiso 1 1 calc R . .
C12 C 0.4983(6) 0.5469(3) 0.30453(18) 0.0521(8) Uani 1 1 d . . .
C11 C 0.6923(7) 0.5857(3) 0.25642(19) 0.0635(10) Uani 1 1 d . . .
H11 H 0.6887 0.5524 0.2074 0.076 Uiso 1 1 calc R . .
H1C H -0.463(8) 0.036(4) 0.754(2) 0.106(14) Uiso 1 1 d . . .
O3 O 0.3238(6) 0.4766(2) 1.08625(14) 0.0861(8) Uani 1 1 d . . .
H3A H -0.155(5) 1.116(3) 0.6003(15) 0.037(8) Uiso 1 1 d . . .
H3B H -0.373(7) 1.082(3) 0.539(2) 0.077(11) 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
O4 S1 O3 120.14(18) . .
O4 S1 N1 105.30(16) . .
O3 S1 N1 107.37(16) . .
O4 S1 C1 108.06(15) . .
O3 S1 C1 108.75(16) . .
N1 S1 C1 106.41(15) . .
C15 N2 C16 118.4(3) . .
O5 C19 N3 121.6(3) . .
O5 C19 C14 119.6(2) . .
N3 C19 C14 118.8(2) . .
N2 C15 C14 123.1(3) . .
C15 C14 C18 117.5(3) . .
C15 C14 C19 123.9(2) . .
C18 C14 C19 118.6(2) . .
C17 C18 C14 119.9(3) . .
C6 C1 C2 120.5(3) . .
C6 C1 S1 119.4(3) . .
C2 C1 S1 119.8(2) . .
O2 C7 O1 123.6(3) . .
O2 C7 C4 121.8(3) . .
O1 C7 C4 114.6(3) . .
N2 C16 C17 122.4(3) . .
C3 C4 C5 119.3(3) . .
C3 C4 C7 119.4(3) . .
C5 C4 C7 121.1(3) . .
C16 C17 C18 118.7(3) . .
C6 C5 C4 120.2(3) . .
C2 C3 C4 120.8(3) . .
C1 C6 C5 119.8(3) . .
C3 C2 C1 119.2(3) . .
C10 N4 C9 116.8(3) . .
C9 C8 C12 117.4(3) . .
C9 C8 C13 123.7(3) . .
C12 C8 C13 118.9(3) . .
O6 C13 N5 121.8(3) . .
O6 C13 C8 119.6(3) . .
N5 C13 C8 118.7(3) . .
N4 C9 C8 124.7(3) . .
N4 C10 C11 123.1(3) . .
C11 C12 C8 117.6(3) . .
C10 C11 C12 120.4(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O4 1.424(2) .
S1 O3 1.424(3) .
S1 N1 1.600(3) .
S1 C1 1.768(3) .
O5 C19 1.233(3) .
O1 C7 1.300(3) .
N3 C19 1.323(4) .
N2 C15 1.332(3) .
N2 C16 1.335(4) .
O2 C7 1.203(4) .
C19 C14 1.494(4) .
C15 C14 1.381(4) .
C14 C18 1.380(4) .
C18 C17 1.374(4) .
C1 C6 1.373(4) .
C1 C2 1.381(4) .
C7 C4 1.493(4) .
C16 C17 1.371(4) .
C4 C3 1.380(4) .
C4 C5 1.380(4) .
C5 C6 1.379(4) .
C3 C2 1.376(4) .
O6 C13 1.230(3) .
N4 C10 1.320(4) .
N4 C9 1.330(3) .
C8 C9 1.387(4) .
C8 C12 1.389(4) .
C8 C13 1.487(4) .
N5 C13 1.335(3) .
C10 C11 1.368(4) .
C12 C11 1.380(4) .
