#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:27:18 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179664 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/17/4511794.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_4511794
loop_
_publ_author_name
'Pinkowicz, Dawid'
'Li, Zhanyong'
'Pietrzyk, Piotr'
'Rams, Michał'
_publ_section_title
;
 New Thiadiazole Dioxide Bridging Ligand with a Stable Radical Form for
 the Construction of Magnetic Coordination Chains
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4878
_journal_paper_doi               10.1021/cg500906w
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C12 H6 N4 S'
_chemical_formula_weight         238.27
_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                 89.883(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8047(8)
_cell_length_b                   14.994(2)
_cell_length_c                   17.142(2)
_cell_measurement_temperature    110(2)
_cell_volume                     977.9(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0888
_diffrn_reflns_av_sigmaI/netI    0.1203
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7122
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.61
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.406
_refine_diff_density_min         -0.915
_refine_diff_density_rms         0.211
_refine_ls_extinction_coef       0.019(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.2141
_refine_ls_R_factor_gt           0.1915
_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)+(0.1456P)²+31.8894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4376
_refine_ls_wR_factor_ref         0.4495
_reflns_number_gt                1381
_reflns_number_total             1998
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg500906w_si_002.cif
_cod_data_source_block           T
_cod_depositor_comments
'Adding full bibliography for 4511791--4511794.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4511794
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
S1 S 0.2200(9) -0.45701(18) 0.08353(17) 0.0257(9) Uani 1 1 d .
N2 N 0.578(3) -0.3456(7) 0.3111(5) 0.026(2) Uani 1 1 d .
N1 N -0.093(3) -0.1721(7) 0.0603(6) 0.028(2) Uani 1 1 d .
N3 N 0.068(3) -0.3584(6) 0.0584(6) 0.027(2) Uani 1 1 d .
C7 C 0.568(3) -0.2093(8) 0.3845(7) 0.026(3) Uani 1 1 d .
H4 H 0.6157 -0.1809 0.4315 0.031 Uiso 1 1 calc R
C2 C 0.070(3) -0.2090(7) 0.1218(6) 0.020(2) Uani 1 1 d .
C4 C 0.318(3) -0.3491(8) 0.1810(7) 0.027(3) Uani 1 1 d .
C8 C 0.412(4) -0.1641(9) 0.3242(7) 0.030(3) Uani 1 1 d .
H3 H 0.3583 -0.1039 0.3296 0.036 Uiso 1 1 calc R
C9 C 0.335(3) -0.2076(8) 0.2556(7) 0.026(3) Uani 1 1 d .
C3 C 0.151(4) -0.3047(8) 0.1188(6) 0.027(3) Uani 1 1 d .
C6 C 0.654(3) -0.3005(9) 0.3735(7) 0.031(3) Uani 1 1 d .
H8 H 0.7723 -0.3298 0.4134 0.037 Uiso 1 1 calc R
C1 C -0.173(4) -0.0852(8) 0.0654(8) 0.036(3) Uani 1 1 d .
H5 H -0.3019 -0.0594 0.0253 0.044 Uiso 1 1 calc R
C12 C -0.072(4) -0.0315(8) 0.1287(8) 0.034(3) Uani 1 1 d .
H1 H -0.1140 0.0296 0.1279 0.041 Uiso 1 1 calc R
C5 C 0.414(3) -0.2992(7) 0.2513(6) 0.022(2) Uani 1 1 d .
C11 C 0.089(3) -0.0702(7) 0.1913(7) 0.023(2) Uani 1 1 d .
H2 H 0.1494 -0.0360 0.2344 0.027 Uiso 1 1 calc R
N4 N 0.369(3) -0.4357(7) 0.1700(6) 0.029(2) Uani 1 1 d .
C10 C 0.164(3) -0.1631(8) 0.1902(7) 0.024(3) 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'
N N 0.0061 0.0033 '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
N4 S1 N3 100.7(5)
C6 N2 C5 116.7(10)
C1 N1 C2 117.0(11)
C3 N3 S1 104.6(8)
C8 C7 C6 118.4(11)
N1 C2 C10 124.8(10)
N1 C2 C3 118.2(10)
C10 C2 C3 117.1(10)
N4 C4 C3 114.9(11)
N4 C4 C5 125.5(10)
C3 C4 C5 119.6(10)
C7 C8 C9 120.2(12)
C8 C9 C5 117.4(11)
C8 C9 C10 122.4(11)
C5 C9 C10 120.1(11)
N3 C3 C4 113.9(10)
N3 C3 C2 124.1(10)
C4 C3 C2 122.0(10)
N2 C6 C7 124.0(11)
N1 C1 C12 123.0(13)
C11 C12 C1 119.1(11)
N2 C5 C9 123.1(11)
N2 C5 C4 117.7(10)
C9 C5 C4 119.2(10)
C12 C11 C10 119.8(11)
C4 N4 S1 105.8(8)
C2 C10 C11 116.1(10)
C2 C10 C9 122.1(10)
C11 C10 C9 121.8(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 N4 1.620(11)
S1 N3 1.646(10)
N2 C6 1.298(16)
N2 C5 1.387(14)
N1 C1 1.341(16)
N1 C2 1.344(15)
N3 C3 1.349(15)
C7 C8 1.372(18)
C7 C6 1.419(18)
C2 C10 1.406(15)
C2 C3 1.468(15)
C4 N4 1.325(15)
C4 C3 1.410(16)
C4 C5 1.465(16)
C8 C9 1.375(17)
C9 C5 1.409(15)
C9 C10 1.459(16)
C1 C12 1.405(19)
C12 C11 1.367(18)
C11 C10 1.421(15)
