#------------------------------------------------------------------------------
#$Date: 2013-01-31 11:32:46 +0000 (Thu, 31 Jan 2013) $
#$Revision: 72868 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/88/7108865.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_7108865
loop_
_publ_author_name
'Stephen M. Winter'
'Aidin R. Balo'
'Ryan J. Roberts'
'Kristina Lekin'
'Abdeljalil Assoud'
'Paul A. Dube'
'Richard T. Oakley'
_publ_section_title
;
 Hybrid dithiazolothiadiazinyl radicals; versatile building blocks for
 magnetic and conductive materials
;
_journal_name_full               Chem.Commun.
_journal_page_first              1603
_journal_volume                  49
_journal_year                    2012
_chemical_formula_moiety         'C13 H9 N4 S3'
_chemical_formula_sum            'C13 H9 N4 S3'
_chemical_formula_weight         317.42
_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                86.286(13)
_cell_angle_beta                 89.883(14)
_cell_angle_gamma                78.867(14)
_cell_formula_units_Z            2
_cell_length_a                   6.9154(15)
_cell_length_b                   9.5271(19)
_cell_length_c                   10.1385(17)
_cell_measurement_reflns_used    427
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      60
_cell_measurement_theta_min      3
_cell_volume                     654.0(2)
_computing_cell_refinement       ApexII
_computing_data_collection       ApexII
_computing_data_reduction        ApexII
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0824
_diffrn_reflns_av_sigmaI/netI    0.0750
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6122
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  0.9972
_exptl_absorpt_correction_T_min  0.8963
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   twinabs
_exptl_crystal_colour            black-red
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             326
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       0.0022(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.619
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         4697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.619
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0712
_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/[\s^2^(Fo^2^)+(0.0110P)^2^+0.0897P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1422
_reflns_number_gt                2833
_reflns_number_total             2664
_reflns_threshold_expression     >2sigma(I)
_[local]_cod_data_source_file    c3cc38503e.txt
_[local]_cod_data_source_block   twin5
_cod_database_code               7108865
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
S1 S 0.18652(19) 0.77225(12) 1.03038(10) 0.0668(4) Uani 1 1 d .
S2 S 0.14342(17) 0.93225(11) 0.87480(10) 0.0570(3) Uani 1 1 d .
S3 S 0.1669(2) 0.74750(12) 0.37292(10) 0.0685(4) Uani 1 1 d .
N1 N 0.2265(5) 0.6296(3) 0.9426(3) 0.0604(10) Uani 1 1 d .
N2 N 0.2448(5) 0.5486(3) 0.7316(3) 0.0514(9) Uani 1 1 d .
N3 N 0.2607(5) 0.4583(3) 0.5265(3) 0.0487(8) Uani 1 1 d .
N4 N 0.2120(5) 0.5872(3) 0.3126(3) 0.0577(9) Uani 1 1 d .
C1 C 0.2152(6) 0.6613(4) 0.8152(4) 0.0468(10) Uani 1 1 d .
C2 C 0.1730(6) 0.8049(4) 0.7585(4) 0.0467(10) Uani 1 1 d .
C3 C 0.1621(6) 0.8319(4) 0.6247(4) 0.0522(10) Uani 1 1 d .
H3 H 0.1386 0.9258 0.5882 0.063 Uiso 1 1 calc R
C4 C 0.1863(6) 0.7190(4) 0.5439(4) 0.0456(10) Uani 1 1 d .
C5 C 0.2310(5) 0.5731(4) 0.5965(3) 0.0435(10) Uani 1 1 d .
C6 C 0.2887(7) 0.4007(4) 0.7922(4) 0.0709(14) Uani 1 1 d .
H6C H 0.3058 0.3341 0.7239 0.106 Uiso 1 1 calc R
H6B H 0.1815 0.3845 0.8477 0.106 Uiso 1 1 calc R
H6A H 0.4074 0.3871 0.8443 0.106 Uiso 1 1 calc R
C7 C 0.2491(6) 0.4715(4) 0.3909(4) 0.0473(10) Uani 1 1 d .
C8 C 0.2884(6) 0.3326(4) 0.3249(4) 0.0466(10) Uani 1 1 d .
C9 C 0.2849(6) 0.3294(4) 0.1886(4) 0.0528(11) Uani 1 1 d .
H9 H 0.2581 0.4146 0.1358 0.063 Uiso 1 1 calc R
C10 C 0.3213(6) 0.1995(4) 0.1311(4) 0.0597(12) Uani 1 1 d .
H10 H 0.3188 0.1978 0.0395 0.072 Uiso 1 1 calc R
C11 C 0.3612(6) 0.0726(4) 0.2077(4) 0.0577(11) Uani 1 1 d .
H11 H 0.3854 -0.0145 0.1684 0.069 Uiso 1 1 calc R
C12 C 0.3650(6) 0.0760(4) 0.3427(4) 0.0562(11) Uani 1 1 d .
H12 H 0.3934 -0.0096 0.3947 0.067 Uiso 1 1 calc R
C13 C 0.3271(6) 0.2051(4) 0.4030(4) 0.0538(11) Uani 1 1 d .
H13 H 0.3276 0.2060 0.4946 0.065 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0882(9) 0.0601(7) 0.0489(6) -0.0129(5) -0.0022(6) -0.0037(6)
S2 0.0666(8) 0.0524(7) 0.0521(6) -0.0178(5) 0.0027(5) -0.0070(5)
S3 0.1154(10) 0.0429(6) 0.0447(6) -0.0026(5) -0.0023(6) -0.0093(6)
N1 0.078(3) 0.054(2) 0.048(2) -0.0118(16) 0.0030(19) -0.0049(19)
N2 0.063(2) 0.043(2) 0.046(2) -0.0046(15) -0.0054(17) -0.0041(17)
N3 0.061(2) 0.0365(18) 0.0478(19) -0.0068(14) 0.0014(17) -0.0069(16)
N4 0.084(3) 0.0319(19) 0.058(2) -0.0075(15) 0.0036(19) -0.0099(18)
C1 0.052(3) 0.045(2) 0.043(2) -0.0118(19) 0.005(2) -0.007(2)
C2 0.046(2) 0.047(2) 0.048(2) -0.0093(18) 0.0003(19) -0.0066(19)
C3 0.056(3) 0.047(2) 0.052(2) -0.0004(18) 0.004(2) -0.008(2)
C4 0.050(3) 0.034(2) 0.051(2) -0.0095(18) 0.002(2) -0.0041(19)
C5 0.042(2) 0.047(2) 0.043(2) -0.0075(18) 0.0035(18) -0.0095(19)
C6 0.108(4) 0.049(3) 0.052(3) 0.005(2) -0.001(3) -0.008(3)
C7 0.053(3) 0.041(2) 0.049(2) -0.0038(18) 0.002(2) -0.0130(19)
C8 0.048(2) 0.036(2) 0.057(2) -0.0071(19) 0.003(2) -0.0105(19)
C9 0.064(3) 0.042(2) 0.053(2) -0.0001(19) 0.001(2) -0.012(2)
C10 0.074(3) 0.060(3) 0.047(2) -0.012(2) -0.001(2) -0.014(2)
C11 0.058(3) 0.045(2) 0.073(3) -0.017(2) 0.001(2) -0.012(2)
C12 0.059(3) 0.041(2) 0.068(3) -0.006(2) -0.001(2) -0.007(2)
C13 0.058(3) 0.050(3) 0.053(2) -0.008(2) -0.003(2) -0.010(2)
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
N1 S1 S2 98.96(13)
C2 S2 S1 91.37(14)
N4 S3 C4 106.53(17)
C1 N1 S1 113.2(3)
C5 N2 C1 121.5(3)
C5 N2 C6 120.4(3)
C1 N2 C6 118.1(3)
C5 N3 C7 120.9(3)
C7 N4 S3 120.8(3)
N1 C1 N2 118.0(3)
N1 C1 C2 123.1(3)
N2 C1 C2 118.9(4)
C3 C2 C1 120.6(4)
C3 C2 S2 126.0(3)
C1 C2 S2 113.4(3)
C2 C3 C4 119.6(4)
C3 C4 C5 121.7(4)
C3 C4 S3 121.4(3)
C5 C4 S3 116.9(3)
N3 C5 N2 116.5(3)
N3 C5 C4 125.9(4)
N2 C5 C4 117.7(3)
N4 C7 N3 129.0(4)
N4 C7 C8 116.0(4)
N3 C7 C8 115.0(3)
C9 C8 C13 119.7(4)
C9 C8 C7 121.4(3)
C13 C8 C7 118.9(4)
C10 C9 C8 119.9(4)
C11 C10 C9 120.8(4)
C12 C11 C10 119.2(4)
C11 C12 C13 121.1(4)
C8 C13 C12 119.3(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 N1 1.652(3)
S1 S2 2.1013(16)
S2 C2 1.729(4)
S3 N4 1.656(3)
S3 C4 1.739(4)
N1 C1 1.306(5)
N2 C5 1.375(4)
N2 C1 1.395(4)
N2 C6 1.477(4)
N3 C5 1.325(4)
N3 C7 1.374(4)
N4 C7 1.299(4)
C1 C2 1.425(5)
C2 C3 1.364(5)
C3 C4 1.379(5)
C4 C5 1.431(5)
C7 C8 1.499(5)
C8 C9 1.386(5)
C8 C13 1.387(5)
C9 C10 1.381(5)
C10 C11 1.375(5)
C11 C12 1.372(5)
C12 C13 1.388(5)