#------------------------------------------------------------------------------
#$Date: 2019-03-05 09:52:05 +0100 (mar 05 de mar de 2019) $
#$Revision: 213973 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/13/7011347.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_7011347
loop_
_publ_author_name
'Bond, Andrew D.'
'Haynes, Delia A.'
'Pask, Christopher M.'
'Rawson, Jeremy M.'
_publ_section_title
;
 Concomitant polymorphs: structural studies on the trimorphic
 dithiadiazolyl radical, ClCNSSN
;
_journal_issue                   12
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              2522
_journal_paper_doi               10.1039/b110922g
_journal_year                    2002
_chemical_formula_moiety         'C Cl N2 S2'
_chemical_formula_sum            'C Cl N2 S2'
_chemical_formula_weight         139.60
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 104.022(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            32
_cell_length_a                   12.3032(2)
_cell_length_b                   21.0874(5)
_cell_length_c                   13.8532(2)
_cell_measurement_reflns_used    22710
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     3487.01(11)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 1997)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ 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  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30456
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.645
_exptl_absorpt_correction_T_max  0.744
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav Blessing (1995)'
_exptl_crystal_colour            blue/black
_exptl_crystal_density_diffrn    2.127
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0322P)²+1.5257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0761
_reflns_number_gt                6811
_reflns_number_total             7903
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b110922g.txt
_cod_data_source_block           jr0133
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7011347
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.87817(15) -0.03414(9) 1.37740(12) 0.0208(4) Uani 1 1 d . . .
N11 N 0.96370(13) 0.00449(8) 1.37604(11) 0.0249(4) Uani 1 1 d . . .
N12 N 0.77543(14) -0.01590(8) 1.37596(12) 0.0257(4) Uani 1 1 d . . .
S11 S 0.92892(4) 0.07945(2) 1.37486(4) 0.02730(11) Uani 1 1 d . . .
S12 S 0.76281(4) 0.06162(2) 1.37441(4) 0.02669(11) Uani 1 1 d . . .
Cl11 Cl 0.90606(4) -0.11389(2) 1.38280(4) 0.03049(12) Uani 1 1 d . . .
C21 C 0.82417(15) -0.03063(9) 1.13207(13) 0.0206(4) Uani 1 1 d . . .
N21 N 0.91332(14) 0.00788(8) 1.14453(12) 0.0250(3) Uani 1 1 d . . .
N22 N 0.72152(14) -0.01188(8) 1.12897(12) 0.0264(4) Uani 1 1 d . . .
S21 S 0.88199(4) 0.08242(2) 1.15757(4) 0.02636(11) Uani 1 1 d . . .
S22 S 0.71207(4) 0.06511(3) 1.14131(4) 0.02790(12) Uani 1 1 d . . .
Cl21 Cl 0.84727(4) -0.10976(2) 1.11783(4) 0.02972(11) Uani 1 1 d . . .
C31 C 0.36891(15) -0.01128(9) 1.36563(13) 0.0215(4) Uani 1 1 d . . .
N31 N 0.32144(13) 0.04487(8) 1.36684(12) 0.0245(3) Uani 1 1 d . . .
N32 N 0.31818(13) -0.06684(8) 1.35735(12) 0.0243(3) Uani 1 1 d . . .
S31 S 0.18600(4) 0.03801(2) 1.36000(3) 0.02411(11) Uani 1 1 d . . .
S32 S 0.18301(4) -0.06045(2) 1.34848(4) 0.02409(11) Uani 1 1 d . . .
Cl31 Cl 0.51205(4) -0.01216(3) 1.37600(4) 0.02879(11) Uani 1 1 d . . .
C41 C 0.31258(15) -0.01049(9) 1.12118(13) 0.0220(4) Uani 1 1 d . . .
N41 N 0.26906(14) 0.04629(8) 1.12597(12) 0.0257(4) Uani 1 1 d . . .
N42 N 0.25924(13) -0.06515(8) 1.11993(12) 0.0239(3) Uani 1 1 d . . .
S41 S 0.13551(4) 0.04219(2) 1.12623(3) 0.02410(11) Uani 1 1 d . . .
S42 S 0.12865(4) -0.05642(2) 1.12506(4) 0.02401(11) Uani 1 1 d . . .
Cl41 Cl 0.45053(4) -0.01423(3) 1.11435(4) 0.02928(12) Uani 1 1 d . . .
C51 C 0.90242(15) 0.25663(9) 1.47936(13) 0.0214(4) Uani 1 1 d . . .
N51 N 0.84777(13) 0.31122(8) 1.47327(11) 0.0238(3) Uani 1 1 d . . .
N52 N 0.85770(13) 0.19963(8) 1.47866(12) 0.0247(3) Uani 1 1 d . . .
S51 S 0.71405(4) 0.30192(2) 1.46652(3) 0.02285(11) Uani 1 1 d . . .
S52 S 0.72360(4) 0.20341(2) 1.47633(4) 0.02392(11) Uani 1 1 d . . .
Cl51 Cl 1.04526(4) 0.26125(3) 1.49175(4) 0.03014(12) Uani 1 1 d . . .
C61 C 0.83869(15) 0.25400(9) 1.23773(13) 0.0211(4) Uani 1 1 d . . .
N61 N 0.78925(13) 0.30915(8) 1.24182(12) 0.0233(3) Uani 1 1 d . . .
N62 N 0.79204(13) 0.19742(8) 1.23760(12) 0.0240(3) Uani 1 1 d . . .
S61 S 0.65779(4) 0.30176(2) 1.24586(3) 0.02207(10) Uani 1 1 d . . .
S62 S 0.65933(4) 0.20327(2) 1.24154(3) 0.02284(11) Uani 1 1 d . . .
Cl61 Cl 0.97727(4) 0.25621(3) 1.23148(4) 0.02979(12) Uani 1 1 d . . .
C71 C 0.41343(16) 0.27062(10) 1.49377(13) 0.0242(4) Uani 1 1 d . . .
N71 N 0.31050(15) 0.25264(9) 1.49192(13) 0.0303(4) Uani 1 1 d . . .
N72 N 0.49671(13) 0.23244(8) 1.48489(12) 0.0277(4) Uani 1 1 d . . .
S71 S 0.29378(4) 0.17568(3) 1.47737(4) 0.03347(13) Uani 1 1 d . . .
S72 S 0.45789(4) 0.15793(3) 1.47061(4) 0.03319(13) Uani 1 1 d . . .
Cl71 Cl 0.44379(4) 0.35014(2) 1.50885(4) 0.03207(12) Uani 1 1 d . . .
C81 C 0.35321(16) 0.27692(9) 1.24755(13) 0.0220(4) Uani 1 1 d . . .
N81 N 0.24968(14) 0.25969(8) 1.24447(13) 0.0269(4) Uani 1 1 d . . .
N82 N 0.43850(14) 0.23708(8) 1.25133(12) 0.0262(4) Uani 1 1 d . . .
S81 S 0.23453(4) 0.18248(3) 1.24416(4) 0.03022(12) Uani 1 1 d . . .
S82 S 0.40151(4) 0.16253(3) 1.25182(4) 0.03070(12) Uani 1 1 d . . .
Cl81 Cl 0.38228(4) 0.35635(2) 1.24618(4) 0.03069(12) 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'
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
N12 C11 N11 125.37(18) . . ?
N12 C11 Cl11 117.94(15) . . ?
N11 C11 Cl11 116.69(14) . . ?
C11 N11 S11 112.62(13) . . ?
C11 N12 S12 112.24(14) . . ?
N11 S11 S12 94.58(6) . . ?
N12 S12 S11 95.18(6) . . ?
N22 C21 N21 124.84(18) . . ?
N22 C21 Cl21 118.33(15) . . ?
N21 C21 Cl21 116.83(14) . . ?
C21 N21 S21 112.82(13) . . ?
C21 N22 S22 112.72(14) . . ?
N21 S21 S22 94.41(6) . . ?
N22 S22 S21 95.18(6) . . ?
N32 C31 N31 126.53(18) . . ?
N32 C31 Cl31 116.60(15) . . ?
N31 C31 Cl31 116.87(14) . . ?
C31 N31 S31 111.30(13) . . ?
C31 N32 S32 112.49(14) . . ?
N31 S31 S32 95.20(6) . . ?
N32 S32 S31 94.44(6) . . ?
N41 C41 N42 125.77(18) . . ?
N41 C41 Cl41 117.44(15) . . ?
N42 C41 Cl41 116.78(15) . . ?
C41 N41 S41 111.69(14) . . ?
C41 N42 S42 112.97(14) . . ?
N41 S41 S42 95.23(6) . . ?
N42 S42 S41 94.26(6) . . ?
N52 C51 N51 125.86(18) . . ?
N52 C51 Cl51 117.65(15) . . ?
N51 C51 Cl51 116.47(15) . . ?
C51 N51 S51 112.76(14) . . ?
C51 N52 S52 111.72(14) . . ?
N51 S51 S52 94.35(6) . . ?
N52 S52 S51 95.17(6) . . ?
N61 C61 N62 126.15(18) . . ?
N61 C61 Cl61 116.66(15) . . ?
N62 C61 Cl61 117.18(15) . . ?
C61 N61 S61 112.73(14) . . ?
C61 N62 S62 111.37(13) . . ?
N61 S61 S62 94.48(6) . . ?
N62 S62 S61 95.26(6) . . ?
N71 C71 N72 125.60(19) . . ?
N71 C71 Cl71 117.58(16) . . ?
N72 C71 Cl71 116.82(15) . . ?
C71 N71 S71 112.23(15) . . ?
C71 N72 S72 112.46(14) . . ?
N71 S71 S72 95.13(7) . . ?
N72 S72 S71 94.58(7) . . ?
N81 C81 N82 124.97(19) . . ?
N81 C81 Cl81 118.21(15) . . ?
N82 C81 Cl81 116.82(14) . . ?
C81 N81 S81 112.53(14) . . ?
C81 N82 S82 112.82(14) . . ?
N81 S81 S82 95.20(6) . . ?
N82 S82 S81 94.47(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C11 N12 1.317(2) . ?
C11 N11 1.335(2) . ?
C11 Cl11 1.714(2) . ?
N11 S11 1.6367(17) . ?
N12 S12 1.6418(18) . ?
S11 S12 2.0765(7) . ?
C21 N22 1.314(2) . ?
C21 N21 1.342(2) . ?
C21 Cl21 1.712(2) . ?
N21 S21 1.6387(17) . ?
N22 S22 1.6396(18) . ?
S21 S22 2.0800(7) . ?
C31 N32 1.319(2) . ?
C31 N31 1.322(2) . ?
C31 Cl31 1.7319(19) . ?
N31 S31 1.6524(16) . ?
N32 S32 1.6431(16) . ?
S31 S32 2.0820(7) . ?
C41 N41 1.320(3) . ?
C41 N42 1.324(2) . ?
C41 Cl41 1.7245(19) . ?
N41 S41 1.6462(17) . ?
N42 S42 1.6358(16) . ?
S41 S42 2.0810(7) . ?
C51 N52 1.321(2) . ?
C51 N51 1.326(2) . ?
C51 Cl51 1.7267(19) . ?
N51 S51 1.6369(16) . ?
N52 S52 1.6443(16) . ?
S51 S52 2.0832(7) . ?
C61 N61 1.320(2) . ?
C61 N62 1.324(3) . ?
C61 Cl61 1.7286(19) . ?
N61 S61 1.6393(16) . ?
N62 S62 1.6515(16) . ?
S61 S62 2.0778(7) . ?
C71 N71 1.316(3) . ?
C71 N72 1.332(3) . ?
C71 Cl71 1.720(2) . ?
N71 S71 1.6422(19) . ?
N72 S72 1.6401(18) . ?
S71 S72 2.0778(8) . ?
C81 N81 1.315(3) . ?
C81 N82 1.335(3) . ?
C81 Cl81 1.714(2) . ?
N81 S81 1.6388(18) . ?
N82 S82 1.6371(18) . ?
S81 S82 2.0744(7) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N12 C11 N11 S11 1.3(2) . . . . ?
Cl11 C11 N11 S11 -177.95(9) . . . . ?
N11 C11 N12 S12 -1.1(2) . . . . ?
Cl11 C11 N12 S12 178.14(9) . . . . ?
C11 N11 S11 S12 -0.74(13) . . . . ?
C11 N12 S12 S11 0.38(13) . . . . ?
N11 S11 S12 N12 0.20(8) . . . . ?
N22 C21 N21 S21 0.9(2) . . . . ?
Cl21 C21 N21 S21 -179.92(9) . . . . ?
N21 C21 N22 S22 0.4(2) . . . . ?
Cl21 C21 N22 S22 -178.78(9) . . . . ?
C21 N21 S21 S22 -1.35(13) . . . . ?
C21 N22 S22 S21 -1.14(14) . . . . ?
N21 S21 S22 N22 1.36(8) . . . . ?
N32 C31 N31 S31 1.8(2) . . . . ?
Cl31 C31 N31 S31 -178.17(9) . . . . ?
N31 C31 N32 S32 -0.2(3) . . . . ?
Cl31 C31 N32 S32 179.76(9) . . . . ?
C31 N31 S31 S32 -2.00(13) . . . . ?
C31 N32 S32 S31 -1.09(13) . . . . ?
N31 S31 S32 N32 1.70(8) . . . . ?
N42 C41 N41 S41 -2.1(2) . . . . ?
Cl41 C41 N41 S41 177.03(9) . . . . ?
N41 C41 N42 S42 0.0(2) . . . . ?
Cl41 C41 N42 S42 -179.14(9) . . . . ?
C41 N41 S41 S42 2.51(14) . . . . ?
C41 N42 S42 S41 1.56(13) . . . . ?
N41 S41 S42 N42 -2.23(8) . . . . ?
N52 C51 N51 S51 1.1(2) . . . . ?
Cl51 C51 N51 S51 -177.54(9) . . . . ?
N51 C51 N52 S52 -3.7(2) . . . . ?
Cl51 C51 N52 S52 174.98(9) . . . . ?
C51 N51 S51 S52 1.38(13) . . . . ?
C51 N52 S52 S51 3.55(13) . . . . ?
N51 S51 S52 N52 -2.70(8) . . . . ?
N62 C61 N61 S61 -0.6(2) . . . . ?
Cl61 C61 N61 S61 179.14(9) . . . . ?
N61 C61 N62 S62 0.9(2) . . . . ?
Cl61 C61 N62 S62 -178.83(9) . . . . ?
C61 N61 S61 S62 0.04(13) . . . . ?
C61 N62 S62 S61 -0.64(13) . . . . ?
N61 S61 S62 N62 0.33(8) . . . . ?
N72 C71 N71 S71 0.2(3) . . . . ?
Cl71 C71 N71 S71 -179.87(10) . . . . ?
N71 C71 N72 S72 0.1(3) . . . . ?
Cl71 C71 N72 S72 -179.84(10) . . . . ?
C71 N71 S71 S72 -0.29(14) . . . . ?
C71 N72 S72 S71 -0.27(14) . . . . ?
N71 S71 S72 N72 0.30(9) . . . . ?
N82 C81 N81 S81 -0.8(2) . . . . ?
Cl81 C81 N81 S81 178.92(10) . . . . ?
N81 C81 N82 S82 0.0(2) . . . . ?
Cl81 C81 N82 S82 -179.74(10) . . . . ?
C81 N81 S81 S82 0.98(14) . . . . ?
C81 N82 S82 S81 0.61(14) . . . . ?
N81 S81 S82 N82 -0.86(9) . . . . ?
