#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/52/1505208.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_1505208
loop_
_publ_author_name
'Babu, N. Jagadeesh'
'Reddy, L. Sreenivas'
'Nangia, Ashwini'
_publ_section_title
;
 Amide−N-Oxide Heterosynthon and Amide Dimer Homosynthon in
 Cocrystals of Carboxamide Drugs and PyridineN-Oxides
;
_journal_issue                   3
_journal_name_full               'Molecular Pharmaceutics'
_journal_page_first              417
_journal_paper_doi               10.1021/mp070014c
_journal_volume                  4
_journal_year                    2007
_chemical_formula_moiety         'C10 H8 N2 O2, 2(C7 H5 N O3 S)'
_chemical_formula_sum            'C24 H18 N4 O8 S2'
_chemical_formula_weight         554.54
_chemical_name_systematic
; 
 1:1 complex of saccharin and bipyridine-N,N'-oxide  
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 104.2800(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.5207(4)
_cell_length_b                   14.0377(9)
_cell_length_c                   13.1232(9)
_cell_measurement_reflns_used    4302
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      2.90
_cell_volume                     1164.12(13)
_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  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6302
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.9578
_exptl_absorpt_correction_T_min  0.9231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0362
_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)+(0.0462P)²+0.6528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0954
_reflns_number_gt                2024
_reflns_number_total             2288
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            mp070014csi20070123_112352.cif
_cod_data_source_block           an477_m
_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)/n  '
_cod_database_code               1505208
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
S1 S 1.11335(7) 0.20152(3) 0.42708(3) 0.02094(15) Uani 1 1 d .
O4 O 1.0680(2) 0.29632(9) 0.38786(11) 0.0320(4) Uani 1 1 d .
O2 O 0.6814(2) 0.02051(9) 0.36859(10) 0.0269(3) Uani 1 1 d .
O3 O 1.3248(2) 0.16885(11) 0.43723(11) 0.0316(3) Uani 1 1 d .
O1 O 0.5379(2) 0.63038(11) 0.34408(10) 0.0328(4) Uani 1 1 d .
N1 N 0.3848(2) 0.59925(11) 0.38486(12) 0.0221(3) Uani 1 1 d .
C10 C 0.0794(3) 0.52224(11) 0.47608(13) 0.0175(4) Uani 1 1 d .
C1 C 0.8093(3) 0.08051(12) 0.40765(13) 0.0197(4) Uani 1 1 d .
C11 C 0.0589(3) 0.51924(12) 0.36755(13) 0.0193(4) Uani 1 1 d .
H11 H -0.0618 0.4897 0.3233 0.023 Uiso 1 1 calc R
C12 C 0.2104(3) 0.55826(13) 0.32382(13) 0.0206(4) Uani 1 1 d .
H12 H 0.1921 0.5563 0.2498 0.025 Uiso 1 1 calc R
C2 C 0.8512(3) 0.11872(12) 0.51700(13) 0.0184(4) Uani 1 1 d .
N2 N 0.9450(2) 0.12515(11) 0.35647(12) 0.0224(3) Uani 1 1 d .
C6 C 0.7983(3) 0.14559(13) 0.68737(14) 0.0251(4) Uani 1 1 d .
H6 H 0.7211 0.1346 0.7389 0.030 Uiso 1 1 calc R
C9 C 0.2556(3) 0.56982(13) 0.53545(14) 0.0228(4) Uani 1 1 d .
H9 H 0.2725 0.5765 0.6091 0.027 Uiso 1 1 calc R
C7 C 0.7388(3) 0.09868(13) 0.59138(14) 0.0223(4) Uani 1 1 d .
H7 H 0.6251 0.0544 0.5772 0.027 Uiso 1 1 calc R
C5 C 0.9683(3) 0.20809(13) 0.70948(15) 0.0278(4) Uani 1 1 d .
H5 H 1.0077 0.2378 0.7765 0.033 Uiso 1 1 calc R
C3 C 1.0170(3) 0.18267(13) 0.53955(14) 0.0200(4) Uani 1 1 d .
C4 C 1.0821(3) 0.22801(14) 0.63545(15) 0.0271(4) Uani 1 1 d .
H4 H 1.1988 0.2707 0.6500 0.032 Uiso 1 1 calc R
C8 C 0.4063(3) 0.60752(14) 0.48976(14) 0.0259(4) Uani 1 1 d .
H8 H 0.5258 0.6395 0.5320 0.031 Uiso 1 1 calc R
H1 H 0.951(4) 0.1155(17) 0.292(2) 0.044(7) 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_3
O3 S1 O4 116.19(9) .
O3 S1 N2 109.75(8) .
O4 S1 N2 110.67(9) .
O3 S1 C3 114.18(8) .
O4 S1 C3 110.88(8) .
N2 S1 C3 92.72(8) .
O1 N1 C12 120.85(15) .
O1 N1 C8 119.04(15) .
C12 N1 C8 120.09(15) .
C9 C10 C11 116.32(15) .
C9 C10 C10 122.34(19) 3_566
C11 C10 C10 121.34(19) 3_566
O2 C1 N2 124.52(16) .
O2 C1 C2 127.05(16) .
N2 C1 C2 108.43(15) .
C12 C11 C10 121.08(16) .
C12 C11 H11 119.5 .
C10 C11 H11 119.5 .
N1 C12 C11 120.69(16) .
N1 C12 H12 119.7 .
C11 C12 H12 119.7 .
C3 C2 C7 120.21(16) .
C3 C2 C1 112.82(15) .
C7 C2 C1 126.92(16) .
C1 N2 S1 116.01(12) .
C1 N2 H1 126.3(16) .
S1 N2 H1 117.7(16) .
C5 C6 C7 121.30(17) .
C5 C6 H6 119.3 .
C7 C6 H6 119.3 .
C8 C9 C10 121.38(16) .
C8 C9 H9 119.3 .
C10 C9 H9 119.3 .
C2 C7 C6 117.67(17) .
C2 C7 H7 121.2 .
C6 C7 H7 121.2 .
C6 C5 C4 121.22(17) .
C6 C5 H5 119.4 .
C4 C5 H5 119.4 .
C2 C3 C4 122.96(17) .
C2 C3 S1 109.92(13) .
C4 C3 S1 126.99(14) .
C3 C4 C5 116.60(18) .
C3 C4 H4 121.7 .
C5 C4 H4 121.7 .
N1 C8 C9 120.26(17) .
N1 C8 H8 119.9 .
C9 C8 H8 119.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O3 1.4277(14) .
S1 O4 1.4312(14) .
S1 N2 1.6467(16) .
S1 C3 1.7610(17) .
O2 C1 1.207(2) .
O1 N1 1.3184(19) .
N1 C12 1.348(2) .
N1 C8 1.354(2) .
C10 C9 1.390(2) .
C10 C11 1.398(2) .
C10 C10 1.475(3) 3_566
C1 N2 1.385(2) .
C1 C2 1.493(2) .
C11 C12 1.373(2) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C2 C3 1.380(2) .
C2 C7 1.386(2) .
N2 H1 0.87(3) .
C6 C5 1.387(3) .
C6 C7 1.389(3) .
C6 H6 0.9500 .
C9 C8 1.377(2) .
C9 H9 0.9500 .
C7 H7 0.9500 .
C5 C4 1.388(3) .
C5 H5 0.9500 .
C3 C4 1.380(3) .
C4 H4 0.9500 .
C8 H8 0.9500 .
