#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:39:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180231 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/17/7111743.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7111743
loop_
_publ_author_name
'Winter, Stephen M.'
'Roberts, Ryan J.'
'Mailman, Aaron'
'Cvrkalj, Kristina'
'Assoud, Abdeljalil'
'Oakley, Richard T.'
_publ_section_title
;
 Thermal conversion of a pyridine-bridged bisdithiazolyl radical to a
 zwitterionic bisdithiazolopyridone
;
_journal_issue                   25
_journal_name_full               'Chemical Communications'
_journal_page_first              4496
_journal_page_last               4498
_journal_paper_doi               10.1039/c0cc00775g
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C6 H3 N3 O S4'
_chemical_formula_weight         261.35
_chemical_name_systematic
;
?
;
_space_group_IT_number           52
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2a 2bc'
_symmetry_space_group_name_H-M   'P n n a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.1845(10)
_cell_length_b                   14.4724(12)
_cell_length_c                   11.3596(10)
_cell_measurement_temperature    296(2)
_cell_volume                     1838.7(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20292
_diffrn_reflns_theta_full        30.46
_diffrn_reflns_theta_max         30.46
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.996
_exptl_absorpt_correction_T_max  0.9537
_exptl_absorpt_correction_T_min  0.8949
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.888
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0375
_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)+(0.0133P)²+1.2977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0747
_reflns_number_gt                2124
_reflns_number_total             2802
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC00775Gsup1.cif
_cod_data_source_block           omebpme_0ma
_cod_database_code               7111743
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x-1/2, -y-1/2, z-1/2'
'-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
S1A S 0.90518(5) 0.58308(4) 0.00799(5) 0.03997(15) Uani 1 1 d .
S2A S 0.74037(5) 0.63533(4) 0.05969(5) 0.03830(15) Uani 1 1 d .
O1A O 0.62074(18) 0.7500 0.2500 0.0399(5) Uani 1 2 d S
N1A N 0.9944(2) 0.7500 0.2500 0.0316(5) Uani 1 2 d S
N2A N 0.98942(16) 0.63945(13) 0.10126(17) 0.0371(4) Uani 1 1 d .
C1A C 0.93232(18) 0.69533(14) 0.17224(18) 0.0290(4) Uani 1 1 d .
C2A C 0.80511(18) 0.69978(14) 0.16879(18) 0.0285(4) Uani 1 1 d .
C3A C 0.7349(3) 0.7500 0.2500 0.0297(6) Uani 1 2 d S
C4A C 1.1257(3) 0.7500 0.2500 0.0523(10) Uani 1 2 d S
H4AA H 1.1543 0.7917 0.3093 0.078 Uiso 1 1 calc R
H4AB H 1.1543 0.7695 0.1743 0.078 Uiso 0.25 1 calc PR
H4AC H 1.1543 0.6888 0.2664 0.078 Uiso 0.25 1 calc PR
S1B S 0.50036(6) 0.66355(5) 0.43845(6) 0.04535(17) Uani 1 1 d .
S2B S 0.43824(5) 0.62033(4) 0.27590(5) 0.03941(15) Uani 1 1 d .
O1B O 0.2500 0.5000 0.15762(19) 0.0418(6) Uani 1 2 d S
N1B N 0.2500 0.5000 0.5258(2) 0.0375(6) Uani 1 2 d S
N2B N 0.40971(19) 0.60355(14) 0.52256(17) 0.0440(5) Uani 1 1 d .
C1B C 0.3314(2) 0.55247(15) 0.46500(19) 0.0343(5) Uani 1 1 d .
C2B C 0.33131(19) 0.55178(15) 0.33924(19) 0.0324(4) Uani 1 1 d .
C3B C 0.2500 0.5000 0.2690(3) 0.0321(6) Uani 1 2 d S
C4B C 0.2500 0.5000 0.6552(3) 0.0498(9) Uani 1 2 d S
H4BA H 0.1880 0.4598 0.6833 0.075 Uiso 1 1 calc R
H4BB H 0.2360 0.5616 0.6833 0.075 Uiso 0.25 1 calc PR
H4BC H 0.3260 0.4786 0.6833 0.075 Uiso 0.25 1 calc PR
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
N2A S1A S2A 98.42(7) . .
C2A S2A S1A 91.59(7) . .
C1A N1A C1A 119.3(2) 4_565 .
C1A N1A C4A 120.35(12) 4_565 .
C1A N1A C4A 120.36(12) . .
C1A N2A S1A 115.23(16) . .
N2A C1A N1A 120.35(19) . .
N2A C1A C2A 119.89(19) . .
N1A C1A C2A 119.76(19) . .
C3A C2A C1A 124.1(2) . .
C3A C2A S2A 121.20(16) . .
C1A C2A S2A 114.69(16) . .
O1A C3A C2A 123.77(13) . 4_565
O1A C3A C2A 123.77(13) . .
C2A C3A C2A 112.5(3) 4_565 .
N2B S1B S2B 98.75(7) . .
C2B S2B S1B 91.99(8) . .
C1B N1B C1B 119.6(3) . 2_565
C1B N1B C4B 120.20(13) . .
C1B N1B C4B 120.20(13) 2_565 .
C1B N2B S1B 114.69(16) . .
N2B C1B N1B 120.1(2) . .
N2B C1B C2B 120.0(2) . .
N1B C1B C2B 119.9(2) . .
C3B C2B C1B 124.4(2) . .
C3B C2B S2B 121.04(17) . .
C1B C2B S2B 114.55(16) . .
O1B C3B C2B 124.11(13) . .
O1B C3B C2B 124.11(13) . 2_565
C2B C3B C2B 111.8(3) . 2_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1A N2A 1.636(2) .
S1A S2A 2.0772(9) .
S2A C2A 1.712(2) .
O1A C3A 1.277(3) .
N1A C1A 1.374(2) 4_565
N1A C1A 1.374(2) .
N1A C4A 1.468(4) .
N2A C1A 1.309(3) .
C1A C2A 1.425(3) .
C2A C3A 1.413(3) .
C3A C2A 1.413(3) 4_565
S1B N2B 1.642(2) .
S1B S2B 2.0696(9) .
S2B C2B 1.712(2) .
O1B C3B 1.265(3) .
N1B C1B 1.372(3) .
N1B C1B 1.372(3) 2_565
N1B C4B 1.470(4) .
N2B C1B 1.319(3) .
C1B C2B 1.429(3) .
C2B C3B 1.423(3) .
C3B C2B 1.423(3) 2_565
