#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:35:18 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179537 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/06/4500672.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_4500672
loop_
_publ_author_name
'Goud, N. Rajesh'
'Babu, N. Jagadeesh'
'Nangia, Ashwini'
_publ_section_title
;
 Sulfonamide−Pyridine-N-oxide Cocrystals
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1930
_journal_paper_doi               10.1021/cg200094x
_journal_volume                  11
_journal_year                    2011
_chemical_formula_sum            'C24 H26 N4 O8 S2'
_chemical_formula_weight         562.61
_chemical_name_systematic
; 
 ? 
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 102.935(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.7426(8)
_cell_length_b                   5.2061(5)
_cell_length_c                   27.7269(19)
_cell_measurement_reflns_used    6603
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      2.39
_cell_volume                     1229.96(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            11917
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  0.9677
_exptl_absorpt_correction_T_min  0.9170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2422
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0397
_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)+(0.0528P)²+0.9406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                2290
_reflns_number_total             2422
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200094x_si_003.cif
_cod_data_source_block           4-MBS-BPNO
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               4500672
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
O3 O 0.68339(18) 1.1907(3) 0.91315(6) 0.0431(4) Uani 1 1 d .
N2 N 0.6366(2) 1.0046(4) 0.93618(6) 0.0328(4) Uani 1 1 d .
C8 C 0.7406(2) 0.8572(4) 0.96844(7) 0.0341(5) Uani 1 1 d .
H8 H 0.8475 0.8909 0.9737 0.041 Uiso 1 1 calc R
C9 C 0.6891(2) 0.6606(4) 0.99312(7) 0.0331(5) Uani 1 1 d .
H9 H 0.7620 0.5618 1.0150 0.040 Uiso 1 1 calc R
C10 C 0.5285(2) 0.6035(4) 0.98639(6) 0.0290(4) Uani 1 1 d .
C11 C 0.4262(2) 0.7562(4) 0.95225(7) 0.0296(4) Uani 1 1 d .
H11 H 0.3189 0.7239 0.9458 0.036 Uiso 1 1 calc R
C12 C 0.4813(2) 0.9521(4) 0.92821(7) 0.0326(5) Uani 1 1 d .
H12 H 0.4106 1.0519 0.9058 0.039 Uiso 1 1 calc R
S1 S 1.03598(5) 0.21531(8) 0.879656(17) 0.02137(15) Uani 1 1 d .
O1 O 1.18204(15) 0.3192(3) 0.87339(5) 0.0313(3) Uani 1 1 d .
O2 O 1.03363(15) -0.0382(3) 0.90032(5) 0.0281(3) Uani 1 1 d .
O4 O 0.60191(16) 0.2406(2) 0.68406(5) 0.0248(3) Uani 1 1 d .
N1 N 0.97046(19) 0.4075(3) 0.91597(6) 0.0265(4) Uani 1 1 d .
H1A H 0.8815 0.3502 0.9192 0.032 Uiso 1 1 d R
H2A H 0.9800 0.5557 0.9069 0.032 Uiso 1 1 d R
C1 C 0.9045(2) 0.2164(3) 0.82134(7) 0.0194(4) Uani 1 1 d .
C2 C 0.7884(2) 0.0302(3) 0.80985(7) 0.0211(4) Uani 1 1 d .
H2 H 0.7800 -0.0954 0.8330 0.025 Uiso 1 1 calc R
C3 C 0.6848(2) 0.0312(3) 0.76399(7) 0.0207(4) Uani 1 1 d .
H3 H 0.6075 -0.0942 0.7561 0.025 Uiso 1 1 calc R
C4 C 0.6974(2) 0.2217(3) 0.72970(7) 0.0196(4) Uani 1 1 d .
C5 C 0.8130(2) 0.4114(3) 0.74177(7) 0.0222(4) Uani 1 1 d .
H5 H 0.8199 0.5399 0.7190 0.027 Uiso 1 1 calc R
C6 C 0.9165(2) 0.4085(3) 0.78721(7) 0.0215(4) Uani 1 1 d .
H6 H 0.9940 0.5337 0.7951 0.026 Uiso 1 1 calc R
C7 C 0.4975(2) 0.0298(4) 0.66765(7) 0.0258(4) Uani 1 1 d .
H7A H 0.5566 -0.1269 0.6702 0.039 Uiso 1 1 calc R
H7B H 0.4439 0.0570 0.6338 0.039 Uiso 1 1 calc R
H7C H 0.4221 0.0182 0.6880 0.039 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 0.0033 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_3
O3 N2 C12 119.57(18) .
O3 N2 C8 120.97(19) .
C12 N2 C8 119.5(2) .
N2 C8 C9 120.4(2) .
N2 C8 H8 119.8 .
C9 C8 H8 119.8 .
C8 C9 C10 121.66(19) .
C8 C9 H9 119.2 .
C10 C9 H9 119.2 .
C11 C10 C9 116.0(2) .
C11 C10 C10 121.8(2) 3_667
C9 C10 C10 122.2(2) 3_667
C12 C11 C10 120.96(19) .
C12 C11 H11 119.5 .
C10 C11 H11 119.5 .
N2 C12 C11 121.48(19) .
N2 C12 H12 119.3 .
C11 C12 H12 119.3 .
O1 S1 O2 119.11(8) .
O1 S1 N1 107.00(9) .
O2 S1 N1 106.34(9) .
O1 S1 C1 107.66(9) .
O2 S1 C1 107.68(8) .
N1 S1 C1 108.73(8) .
C4 O4 C7 117.12(14) .
S1 N1 H1A 107.9 .
S1 N1 H2A 108.6 .
H1A N1 H2A 121.0 .
C2 C1 C6 120.43(16) .
C2 C1 S1 120.11(14) .
C6 C1 S1 119.46(13) .
C3 C2 C1 120.13(17) .
C3 C2 H2 119.9 .
C1 C2 H2 119.9 .
C2 C3 C4 119.53(16) .
C2 C3 H3 120.2 .
C4 C3 H3 120.2 .
O4 C4 C3 124.20(16) .
O4 C4 C5 115.67(16) .
C3 C4 C5 120.13(17) .
C6 C5 C4 120.18(16) .
C6 C5 H5 119.9 .
C4 C5 H5 119.9 .
C5 C6 C1 119.61(16) .
C5 C6 H6 120.2 .
C1 C6 H6 120.2 .
O4 C7 H7A 109.5 .
O4 C7 H7B 109.5 .
H7A C7 H7B 109.5 .
O4 C7 H7C 109.5 .
H7A C7 H7C 109.5 .
H7B C7 H7C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 N2 1.277(2) .
N2 C12 1.353(3) .
N2 C8 1.361(3) .
C8 C9 1.363(3) .
C8 H8 0.9300 .
C9 C10 1.406(3) .
C9 H9 0.9300 .
C10 C11 1.396(3) .
C10 C10 1.465(4) 3_667
C11 C12 1.364(3) .
C11 H11 0.9300 .
C12 H12 0.9300 .
S1 O1 1.4327(14) .
S1 O2 1.4409(14) .
S1 N1 1.6126(16) .
S1 C1 1.7617(18) .
O4 C4 1.355(2) .
O4 C7 1.435(2) .
N1 H1A 0.8557 .
N1 H2A 0.8215 .
C1 C2 1.388(2) .
C1 C6 1.397(2) .
C2 C3 1.386(3) .
C2 H2 0.9300 .
C3 C4 1.395(2) .
C3 H3 0.9300 .
C4 C5 1.399(3) .
C5 C6 1.377(3) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
