#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:35:18 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179537 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/06/4500670.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_4500670
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            'C22 H20 Br2 N4 O6 S2'
_chemical_formula_weight         660.36
_chemical_name_systematic
; 
 ? 
;
_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
_cell_angle_alpha                98.774(6)
_cell_angle_beta                 95.521(6)
_cell_angle_gamma                114.520(6)
_cell_formula_units_Z            1
_cell_length_a                   8.181(3)
_cell_length_b                   8.421(3)
_cell_length_c                   10.250(4)
_cell_measurement_reflns_used    4286
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      2.04
_cell_volume                     624.9(4)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6340
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    3.457
_exptl_absorpt_correction_T_max  0.4908
_exptl_absorpt_correction_T_min  0.2877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             330
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0299
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0476P)²+0.0845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0764
_reflns_number_gt                2207
_reflns_number_total             2406
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200094x_si_001.cif
_cod_data_source_block           2BBS-BPNO
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               4500670
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
O3 O 0.2778(2) 0.9786(2) 0.10593(17) 0.0575(5) Uani 1 1 d .
N2 N 0.2029(3) 0.9843(3) 0.21365(18) 0.0430(4) Uani 1 1 d .
C11 C 0.1513(4) 1.1146(3) 0.2501(2) 0.0528(6) Uani 1 1 d .
H11 H 0.1701 1.2010 0.1991 0.063 Uiso 1 1 calc R
C10 C 0.0721(4) 1.1220(3) 0.3604(2) 0.0490(6) Uani 1 1 d .
H10 H 0.0366 1.2128 0.3827 0.059 Uiso 1 1 calc R
C9 C 0.0431(3) 0.9970(3) 0.44045(19) 0.0334(4) Uani 1 1 d .
C8 C 0.0991(3) 0.8647(3) 0.4004(2) 0.0386(5) Uani 1 1 d .
H8 H 0.0838 0.7782 0.4508 0.046 Uiso 1 1 calc R
C7 C 0.1763(3) 0.8598(3) 0.2880(2) 0.0426(5) Uani 1 1 d .
H7 H 0.2110 0.7690 0.2626 0.051 Uiso 1 1 calc R
Br1 Br 0.82727(3) 0.57840(3) -0.00052(2) 0.04752(11) Uani 1 1 d .
S1 S 0.75250(8) 0.35041(7) 0.25161(6) 0.04171(15) Uani 1 1 d .
O2 O 0.6865(3) 0.2798(2) 0.36483(18) 0.0633(5) Uani 1 1 d .
O1 O 0.9444(2) 0.4243(2) 0.2500(2) 0.0569(5) Uani 1 1 d .
N1 N 0.6512(3) 0.1960(2) 0.1226(2) 0.0508(5) Uani 1 1 d .
H1B H 0.5369 0.1282 0.1245 0.061 Uiso 1 1 d R
H1A H 0.6997 0.1999 0.0575 0.061 Uiso 1 1 d R
C1 C 0.6814(3) 0.5229(3) 0.2428(2) 0.0346(4) Uani 1 1 d .
C2 C 0.5960(3) 0.5628(3) 0.3447(2) 0.0452(5) Uani 1 1 d .
H2 H 0.5707 0.4946 0.4099 0.054 Uiso 1 1 calc R
C3 C 0.5479(4) 0.7027(3) 0.3507(3) 0.0504(6) Uani 1 1 d .
H3 H 0.4894 0.7276 0.4190 0.061 Uiso 1 1 calc R
C4 C 0.5874(3) 0.8052(3) 0.2546(3) 0.0500(6) Uani 1 1 d .
H4 H 0.5585 0.9015 0.2596 0.060 Uiso 1 1 calc R
C5 C 0.6689(3) 0.7658(3) 0.1520(2) 0.0438(5) Uani 1 1 d .
H5 H 0.6939 0.8346 0.0872 0.053 Uiso 1 1 calc R
C6 C 0.7145(3) 0.6238(3) 0.1443(2) 0.0347(4) Uani 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'
S S 0.1246 0.1234 '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'
Br Br -0.2901 2.4595 '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 C11 120.1(2) .
O3 N2 C7 120.5(2) .
C11 N2 C7 119.34(19) .
N2 C11 C10 121.1(2) .
N2 C11 H11 119.5 .
C10 C11 H11 119.5 .
C11 C10 C9 121.5(2) .
C11 C10 H10 119.2 .
C9 C10 H10 119.2 .
C10 C9 C8 115.87(19) .
C10 C9 C9 122.1(2) 2_576
C8 C9 C9 122.0(2) 2_576
C7 C8 C9 121.1(2) .
C7 C8 H8 119.4 .
C9 C8 H8 119.4 .
N2 C7 C8 121.0(2) .
N2 C7 H7 119.5 .
C8 C7 H7 119.5 .
O1 S1 O2 119.05(13) .
O1 S1 N1 108.22(11) .
O2 S1 N1 107.35(12) .
O1 S1 C1 107.76(10) .
O2 S1 C1 105.35(10) .
N1 S1 C1 108.77(11) .
S1 N1 H1B 114.0 .
S1 N1 H1A 118.5 .
H1B N1 H1A 126.0 .
C2 C1 C6 118.75(19) .
C2 C1 S1 117.12(15) .
C6 C1 S1 124.06(16) .
C3 C2 C1 120.9(2) .
C3 C2 H2 119.5 .
C1 C2 H2 119.5 .
C4 C3 C2 119.5(2) .
C4 C3 H3 120.3 .
C2 C3 H3 120.3 .
C5 C4 C3 120.3(2) .
C5 C4 H4 119.8 .
C3 C4 H4 119.8 .
C4 C5 C6 120.3(2) .
C4 C5 H5 119.8 .
C6 C5 H5 119.8 .
C5 C6 C1 120.1(2) .
C5 C6 Br1 117.71(16) .
C1 C6 Br1 122.14(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 N2 1.318(2) .
N2 C11 1.345(3) .
N2 C7 1.347(3) .
C11 C10 1.362(3) .
C11 H11 0.9300 .
C10 C9 1.389(3) .
C10 H10 0.9300 .
C9 C8 1.393(3) .
C9 C9 1.472(4) 2_576
C8 C7 1.369(3) .
C8 H8 0.9300 .
C7 H7 0.9300 .
Br1 C6 1.894(2) .
S1 O1 1.431(2) .
S1 O2 1.4340(19) .
S1 N1 1.580(2) .
S1 C1 1.786(2) .
N1 H1B 0.8743 .
N1 H1A 0.8070 .
C1 C2 1.386(3) .
C1 C6 1.392(3) .
C2 C3 1.383(3) .
C2 H2 0.9300 .
C3 C4 1.382(3) .
C3 H3 0.9300 .
C4 C5 1.368(4) .
C4 H4 0.9300 .
C5 C6 1.386(3) .
C5 H5 0.9300 .
