#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/83/2018329.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2018329
loop_
_publ_author_name
'Pratt, Jamal'
'Hutchinson, Janna'
'Klein Stevens, Cheryl L.'
_publ_section_title
;
 Sulfapyridine (polymorph III), sulfapyridine dioxane solvate,
 sulfapyridine tetrahydrofuran solvate and sulfapyridine piperidine
 solvate, all at 173K
;
_journal_coeditor_code           QS3006
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o487
_journal_page_last               o491
_journal_paper_doi               10.1107/S0108270111041825
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H11 N3 O2 S'
_chemical_formula_moiety         'C11 H11 N3 O2 S'
_chemical_formula_sum            'C11 H11 N3 O2 S'
_chemical_formula_weight         249.29
_chemical_name_common            'sulfapyridine III'
_chemical_name_systematic
;
4-amino-N-(1,2-dihydropyridin-2-ylidene)benzenesulfonamide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.546(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.7350(16)
_cell_length_b                   11.6945(15)
_cell_length_c                   15.3357(18)
_cell_measurement_reflns_used    3053
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.003
_cell_measurement_theta_min      2.666
_cell_volume                     2279.6(5)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6574
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  0.9093
_exptl_absorpt_correction_T_min  0.8192
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.400
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0347
_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)+(0.0447P)²+2.3901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0960
_reflns_number_gt                1743
_reflns_number_total             1987
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qs3006.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2018329
_cod_database_fobs_code          2018329
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'
'-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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.20295(3) 0.04278(3) 0.56159(3) 0.01977(17) Uani d . 1 1
O O1 0.13357(11) -0.05260(10) 0.54268(9) 0.0276(3) Uani d . 1 1
O O2 0.20233(10) 0.13306(10) 0.49613(8) 0.0244(3) Uani d . 1 1
N N1 0.31848(12) -0.01057(12) 0.58007(11) 0.0235(4) Uani d . 1 1
N N2 0.40667(13) 0.17069(13) 0.57700(11) 0.0228(4) Uani d . 1 1
N N3 0.12411(15) 0.23650(15) 0.90740(12) 0.0313(4) Uani d . 1 1
C C1 0.16910(13) 0.10389(15) 0.66023(12) 0.0200(4) Uani d . 1 1
C C2 0.14436(14) 0.03156(15) 0.72860(13) 0.0227(4) Uani d . 1 1
H H2 0.1390 -0.0485 0.7188 0.027 Uiso calc R 1 1
C C3 0.12780(14) 0.07514(15) 0.80965(12) 0.0232(4) Uani d . 1 1
H H3 0.1101 0.0251 0.8553 0.028 Uiso calc R 1 1
C C4 0.13683(14) 0.19362(15) 0.82585(12) 0.0220(4) Uani d . 1 1
C C5 0.15854(15) 0.26569(15) 0.75575(13) 0.0245(4) Uani d . 1 1
H H5 0.1618 0.3460 0.7647 0.029 Uiso calc R 1 1
C C6 0.17511(14) 0.22172(15) 0.67432(12) 0.0225(4) Uani d . 1 1
H H6 0.1906 0.2715 0.6279 0.027 Uiso calc R 1 1
C C7 0.40435(15) 0.05569(15) 0.59211(12) 0.0219(4) Uani d . 1 1
C C8 0.50124(15) 0.00607(18) 0.62270(14) 0.0327(5) Uani d . 1 1
H H8 0.5050 -0.0740 0.6331 0.039 Uiso calc R 1 1
C C9 0.58889(17) 0.07112(19) 0.63746(16) 0.0402(6) Uani d . 1 1
H H9 0.6530 0.0361 0.6581 0.048 Uiso calc R 1 1
C C10 0.58575(16) 0.19013(18) 0.62248(15) 0.0372(5) Uani d . 1 1
H H10 0.6467 0.2360 0.6337 0.045 Uiso calc R 1 1
C C11 0.49401(15) 0.23712(17) 0.59179(13) 0.0297(5) Uani d . 1 1
H H11 0.4902 0.3169 0.5804 0.036 Uiso calc R 1 1
H H1 0.352(2) 0.203(2) 0.5520(15) 0.038(6) Uiso d . 1 1
H H3A 0.1224(19) 0.186(2) 0.9494(16) 0.044(7) Uiso d . 1 1
H H3B 0.1467(19) 0.303(2) 0.9171(16) 0.044(7) Uiso d . 1 1
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
O1 S1 O2 116.43(8)
O1 S1 N1 106.15(8)
O2 S1 N1 111.65(8)
O1 S1 C1 108.00(8)
O2 S1 C1 107.97(8)
N1 S1 C1 106.12(8)
C7 N1 S1 121.92(13)
C11 N2 C7 123.97(17)
C11 N2 H1 117.3(15)
C7 N2 H1 118.5(15)
C4 N3 H3A 116.1(16)
C4 N3 H3B 116.3(17)
H3A N3 H3B 121(2)
C6 C1 C2 119.59(17)
C6 C1 S1 121.49(14)
C2 C1 S1 118.68(13)
C3 C2 C1 120.61(16)
C3 C2 H2 119.7
C1 C2 H2 119.7
C2 C3 C4 120.59(17)
C2 C3 H3 119.7
C4 C3 H3 119.7
N3 C4 C5 121.30(17)
N3 C4 C3 120.57(17)
C5 C4 C3 118.13(17)
C6 C5 C4 121.13(16)
C6 C5 H5 119.4
C4 C5 H5 119.4
C5 C6 C1 119.88(17)
C5 C6 H6 120.1
C1 C6 H6 120.1
N1 C7 N2 124.80(17)
N1 C7 C8 119.60(17)
N2 C7 C8 115.60(17)
C9 C8 C7 121.04(19)
C9 C8 H8 119.5
C7 C8 H8 119.5
C8 C9 C10 120.70(19)
C8 C9 H9 119.6
C10 C9 H9 119.6
C11 C10 C9 118.29(19)
C11 C10 H10 120.9
C9 C10 H10 120.9
C10 C11 N2 120.37(18)
C10 C11 H11 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4413(13)
S1 O2 1.4566(13)
S1 N1 1.6070(15)
S1 C1 1.7509(18)
N1 C7 1.344(2)
N2 C11 1.364(2)
N2 C7 1.365(2)
N2 H1 0.86(3)
N3 C4 1.366(3)
N3 H3A 0.87(3)
N3 H3B 0.84(3)
C1 C6 1.396(2)
C1 C2 1.398(3)
C2 C3 1.372(3)
C2 H2 0.9500
C3 C4 1.411(2)
C3 H3 0.9500
C4 C5 1.407(3)
C5 C6 1.379(3)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.417(3)
C8 C9 1.358(3)
C8 H8 0.9500
C9 C10 1.411(3)
C9 H9 0.9500
C10 C11 1.349(3)
C10 H10 0.9500
C11 H11 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H1 O2 7_556 0.86(3) 2.15(2) 2.874(2) 140(2)
N2 H1 O2 . 0.86(3) 2.19(2) 2.847(2) 132(2)
N3 H1A O1 6_556 0.87(3) 2.12(3) 2.985(2) 172(2)
N3 H1B N1 4_556 0.84(3) 2.23(3) 3.050(2) 168(2)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 S1 N1 C7 173.78(14)
O2 S1 N1 C7 45.93(17)
C1 S1 N1 C7 -71.48(16)
O1 S1 C1 C6 -144.54(15)
O2 S1 C1 C6 -17.86(17)
N1 S1 C1 C6 101.98(16)
O1 S1 C1 C2 41.03(16)
O2 S1 C1 C2 167.72(13)
N1 S1 C1 C2 -72.44(15)
C6 C1 C2 C3 -1.1(3)
S1 C1 C2 C3 173.39(14)
C1 C2 C3 C4 -0.9(3)
C2 C3 C4 N3 -177.60(18)
C2 C3 C4 C5 2.8(3)
N3 C4 C5 C6 177.62(18)
C3 C4 C5 C6 -2.8(3)
C4 C5 C6 C1 0.8(3)
C2 C1 C6 C5 1.2(3)
S1 C1 C6 C5 -173.21(14)
S1 N1 C7 N2 -10.6(3)
S1 N1 C7 C8 169.32(15)
C11 N2 C7 N1 178.21(18)
C11 N2 C7 C8 -1.8(3)
N1 C7 C8 C9 -178.5(2)
N2 C7 C8 C9 1.5(3)
C7 C8 C9 C10 -0.1(4)
C8 C9 C10 C11 -1.1(4)
C9 C10 C11 N2 0.9(3)
C7 N2 C11 C10 0.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5145
