#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:31:46 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179849 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/45/7014581.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_7014581
loop_
_publ_author_name
'Decken, A.'
'Mailman, A.'
'Passmore, J.'
'Rautiainen, J. M.'
'Scherer, W.'
'Scheidt, E.-W.'
_publ_section_title
;
 A prototype hybrid 7π quinone-fused 1,3,2-dithiazolyl radical.
;
_journal_issue                   4
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              868
_journal_page_last               879
_journal_paper_doi               10.1039/c0dt00967a
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         '2(C10 H4 N O2 S2), 2(As F6), O2 S'
_chemical_formula_sum            'C20 H8 As2 F12 N2 O6 S5'
_chemical_formula_weight         910.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.503(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9040(17)
_cell_length_b                   15.1495(18)
_cell_length_c                   14.0456(18)
_cell_measurement_reflns_used    5951
_cell_measurement_temperature    198(1)
_cell_measurement_theta_max      25.640
_cell_measurement_theta_min      2.626
_cell_volume                     2917.9(6)
_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      198(1)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14046
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.48
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker AXS SMART1000/P4'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.767
_exptl_absorpt_correction_T_max  0.7616
_exptl_absorpt_correction_T_min  0.5392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997a)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    2.072
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         4925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0313
_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)+(0.0374P)²+2.6027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0848
_reflns_number_gt                4047
_reflns_number_total             4925
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            C0DT00967A.TXT
_cod_data_source_block           JP030443
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7014581
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
S1 S 0.30298(6) 0.18846(5) 0.43808(6) 0.0296(2) Uani 1 1 d . . .
S2 S 0.43340(6) 0.19367(6) 0.60454(6) 0.0290(2) Uani 1 1 d . . .
N1 N 0.4131(2) 0.20317(18) 0.48950(19) 0.0312(6) Uani 1 1 d . . .
C1 C 0.1476(2) 0.1459(2) 0.5346(2) 0.0263(7) Uani 1 1 d . . .
C2 C 0.2527(2) 0.16689(18) 0.5376(2) 0.0217(7) Uani 1 1 d . . .
C3 C 0.3182(2) 0.16979(18) 0.6210(2) 0.0214(7) Uani 1 1 d . . .
C4 C 0.2900(2) 0.15559(19) 0.7180(2) 0.0225(7) Uani 1 1 d . . .
C5 C 0.1551(3) 0.1164(2) 0.8037(3) 0.0325(8) Uani 1 1 d . . .
C6 C 0.0583(3) 0.0952(3) 0.8051(3) 0.0411(9) Uani 1 1 d . . .
C7 C -0.0071(3) 0.0904(3) 0.7207(3) 0.0441(10) Uani 1 1 d . . .
C8 C 0.0224(3) 0.1070(2) 0.6328(3) 0.0366(8) Uani 1 1 d . . .
C9 C 0.1184(2) 0.1285(2) 0.6296(2) 0.0256(7) Uani 1 1 d . . .
C10 C 0.1863(2) 0.13313(19) 0.7161(2) 0.0247(7) Uani 1 1 d . . .
O1 O 0.09308(17) 0.14366(17) 0.45771(17) 0.0393(6) Uani 1 1 d . . .
O2 O 0.35023(16) 0.16321(15) 0.78980(16) 0.0310(5) Uani 1 1 d . . .
S11 S 0.55797(7) 0.34760(7) 0.39797(7) 0.0414(2) Uani 1 1 d . . .
S12 S 0.71299(7) 0.31702(5) 0.30939(6) 0.0340(2) Uani 1 1 d . . .
N11 N 0.5976(2) 0.32922(18) 0.2996(2) 0.0375(7) Uani 1 1 d . . .
C11 C 0.6755(3) 0.3581(3) 0.5800(3) 0.0471(10) Uani 1 1 d . . .
C12 C 0.6657(2) 0.3457(2) 0.4743(2) 0.0327(8) Uani 1 1 d . . .
C13 C 0.7438(2) 0.32981(19) 0.4298(2) 0.0271(7) Uani 1 1 d . . .
C14 C 0.8454(3) 0.3258(2) 0.4838(2) 0.0303(8) Uani 1 1 d . . .
C15 C 0.9473(3) 0.3399(2) 0.6442(3) 0.0407(9) Uani 1 1 d . . .
C16 C 0.9604(3) 0.3550(3) 0.7419(3) 0.0491(10) Uani 1 1 d . . .
C17 C 0.8811(3) 0.3749(3) 0.7864(3) 0.0462(10) Uani 1 1 d . . .
C18 C 0.7896(3) 0.3774(3) 0.7331(3) 0.0412(9) Uani 1 1 d . . .
C19 C 0.7754(3) 0.3607(2) 0.6345(2) 0.0327(8) Uani 1 1 d . . .
C20 C 0.8557(2) 0.3424(2) 0.5892(2) 0.0284(7) Uani 1 1 d . . .
O11 O 0.6020(2) 0.3628(4) 0.6162(2) 0.1077(16) Uani 1 1 d . . .
O12 O 0.91217(18) 0.30943(17) 0.44106(18) 0.0439(6) Uani 1 1 d . . .
H5 H 0.199(2) 0.117(2) 0.859(3) 0.029(9) Uiso 1 1 d . . .
H6 H 0.041(3) 0.080(3) 0.864(3) 0.062(14) Uiso 1 1 d . . .
H7 H -0.067(3) 0.074(2) 0.721(3) 0.039(10) Uiso 1 1 d . . .
H8 H -0.018(2) 0.107(2) 0.575(3) 0.026(9) Uiso 1 1 d . . .
H15 H 0.996(3) 0.330(3) 0.619(3) 0.045(12) Uiso 1 1 d . . .
H16 H 1.020(3) 0.357(2) 0.777(3) 0.042(11) Uiso 1 1 d . . .
H17 H 0.895(3) 0.388(2) 0.858(3) 0.044(10) Uiso 1 1 d . . .
H18 H 0.741(3) 0.396(2) 0.761(3) 0.043(11) Uiso 1 1 d . . .
As1 As 0.70333(2) 0.08320(2) 0.52469(3) 0.03067(12) Uani 1 1 d . . .
As2 As 0.23108(3) 0.41615(2) 0.60542(3) 0.03122(12) Uani 1 1 d . . .
F1 F 0.6400(2) 0.1438(2) 0.5941(2) 0.0904(10) Uani 1 1 d . . .
F2 F 0.7653(2) 0.02444(15) 0.4512(2) 0.0729(8) Uani 1 1 d . . .
F3 F 0.75249(19) 0.02022(18) 0.62041(19) 0.0719(8) Uani 1 1 d . . .
F4 F 0.61020(17) 0.00955(17) 0.49934(18) 0.0651(7) Uani 1 1 d . . .
F5 F 0.65258(17) 0.14587(13) 0.42698(16) 0.0519(6) Uani 1 1 d . . .
F6 F 0.79706(16) 0.15612(14) 0.5475(2) 0.0674(8) Uani 1 1 d . . .
F7 F 0.31396(16) 0.48877(13) 0.66737(15) 0.0478(6) Uani 1 1 d . . .
F8 F 0.15141(15) 0.34214(13) 0.54266(16) 0.0468(5) Uani 1 1 d . . .
F9 F 0.21554(19) 0.48596(13) 0.50831(16) 0.0596(7) Uani 1 1 d . . .
F10 F 0.32420(16) 0.36562(13) 0.56058(18) 0.0497(6) Uani 1 1 d . . .
F11 F 0.24855(19) 0.34565(14) 0.70164(16) 0.0566(6) Uani 1 1 d . . .
F12 F 0.13933(19) 0.46852(17) 0.6486(2) 0.0725(8) Uani 1 1 d . . .
S20 S 0.47728(7) 0.43653(7) 0.80596(7) 0.0390(2) Uani 1 1 d . . .
O21 O 0.5377(2) 0.49820(18) 0.7701(2) 0.0648(9) Uani 1 1 d . . .
O22 O 0.4743(2) 0.34912(18) 0.7754(2) 0.0608(8) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
As As 0.0499 2.0058 '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
N1 S1 C2 98.59(15) . . ?
N1 S2 C3 98.27(15) . . ?
S1 N1 S2 116.11(17) . . ?
O1 C1 C9 125.0(3) . . ?
O1 C1 C2 119.8(3) . . ?
C9 C1 C2 115.2(3) . . ?
C3 C2 C1 123.1(3) . . ?
C3 C2 S1 113.2(2) . . ?
C1 C2 S1 123.7(2) . . ?
C2 C3 C4 122.7(3) . . ?
C2 C3 S2 113.8(2) . . ?
C4 C3 S2 123.5(2) . . ?
O2 C4 C10 125.3(3) . . ?
O2 C4 C3 119.9(3) . . ?
C10 C4 C3 114.8(3) . . ?
C6 C5 C10 119.9(4) . . ?
C6 C5 H5 120(2) . . ?
C10 C5 H5 120(2) . . ?
C7 C6 C5 120.4(4) . . ?
C7 C6 H6 122(3) . . ?
C5 C6 H6 118(3) . . ?
C6 C7 C8 120.6(4) . . ?
C6 C7 H7 120(3) . . ?
C8 C7 H7 119(3) . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 116(2) . . ?
C7 C8 H8 124(2) . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 C1 118.7(3) . . ?
C10 C9 C1 121.6(3) . . ?
C5 C10 C9 119.4(3) . . ?
C5 C10 C4 118.1(3) . . ?
C9 C10 C4 122.5(3) . . ?
N11 S11 C12 98.61(17) . . ?
N11 S12 C13 99.10(16) . . ?
S11 N11 S12 115.58(18) . . ?
O11 C11 C19 124.6(4) . . ?
O11 C11 C12 118.8(4) . . ?
C19 C11 C12 116.6(3) . . ?
C13 C12 C11 122.3(3) . . ?
C13 C12 S11 113.7(3) . . ?
C11 C12 S11 124.0(3) . . ?
C12 C13 C14 122.4(3) . . ?
C12 C13 S12 113.0(3) . . ?
C14 C13 S12 124.6(3) . . ?
O12 C14 C20 125.0(3) . . ?
O12 C14 C13 119.7(3) . . ?
C20 C14 C13 115.3(3) . . ?
C16 C15 C20 120.9(4) . . ?
C16 C15 H15 119(3) . . ?
C20 C15 H15 120(3) . . ?
C15 C16 C17 120.2(4) . . ?
C15 C16 H16 121(3) . . ?
C17 C16 H16 118(3) . . ?
C18 C17 C16 119.8(4) . . ?
C18 C17 H17 123(2) . . ?
C16 C17 H17 117(2) . . ?
C17 C18 C19 120.5(4) . . ?
C17 C18 H18 119(3) . . ?
C19 C18 H18 120(3) . . ?
C18 C19 C20 119.7(3) . . ?
C18 C19 C11 119.3(3) . . ?
C20 C19 C11 120.9(3) . . ?
C15 C20 C19 118.9(3) . . ?
C15 C20 C14 118.8(3) . . ?
C19 C20 C14 122.3(3) . . ?
F1 As1 F3 91.65(15) . . ?
F1 As1 F6 89.72(15) . . ?
F3 As1 F6 91.17(13) . . ?
F1 As1 F2 177.87(15) . . ?
F3 As1 F2 90.49(14) . . ?
F6 As1 F2 90.28(14) . . ?
F1 As1 F4 91.47(16) . . ?
F3 As1 F4 89.43(12) . . ?
F6 As1 F4 178.65(14) . . ?
F2 As1 F4 88.51(14) . . ?
F1 As1 F5 88.63(14) . . ?
F3 As1 F5 179.23(12) . . ?
F6 As1 F5 89.55(12) . . ?
F2 As1 F5 89.24(13) . . ?
F4 As1 F5 89.84(11) . . ?
F12 As2 F11 91.51(14) . . ?
F12 As2 F10 178.65(13) . . ?
F11 As2 F10 89.66(12) . . ?
F12 As2 F9 89.58(14) . . ?
F11 As2 F9 178.90(13) . . ?
F10 As2 F9 89.24(12) . . ?
F12 As2 F8 91.69(12) . . ?
F11 As2 F8 89.61(11) . . ?
F10 As2 F8 88.98(10) . . ?
F9 As2 F8 90.49(11) . . ?
F12 As2 F7 90.03(12) . . ?
F11 As2 F7 90.22(10) . . ?
F10 As2 F7 89.31(11) . . ?
F9 As2 F7 89.65(10) . . ?
F8 As2 F7 178.28(11) . . ?
O22 S20 O21 120.8(2) . . ?
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
S1 N1 1.597(3) . ?
S1 C2 1.695(3) . ?
S2 N1 1.600(3) . ?
S2 C3 1.695(3) . ?
C1 O1 1.213(4) . ?
C1 C9 1.480(4) . ?
C1 C2 1.489(4) . ?
C2 C3 1.361(4) . ?
C3 C4 1.494(4) . ?
C4 O2 1.205(4) . ?
C4 C10 1.478(4) . ?
C5 C6 1.388(5) . ?
C5 C10 1.392(5) . ?
C5 H5 0.91(3) . ?
C6 C7 1.372(6) . ?
C6 H6 0.92(5) . ?
C7 C8 1.387(6) . ?
C7 H7 0.87(4) . ?
C8 C9 1.383(5) . ?
C8 H8 0.91(3) . ?
C9 C10 1.412(4) . ?
S11 N11 1.594(3) . ?
S11 C12 1.692(3) . ?
S12 N11 1.598(3) . ?
S12 C13 1.686(3) . ?
C11 O11 1.216(5) . ?
C11 C19 1.471(5) . ?
C11 C12 1.481(5) . ?
C12 C13 1.361(5) . ?
C13 C14 1.490(5) . ?
C14 O12 1.211(4) . ?
C14 C20 1.485(5) . ?
C15 C16 1.374(6) . ?
C15 C20 1.377(5) . ?
C15 H15 0.83(4) . ?
C16 C17 1.387(6) . ?
C16 H16 0.89(4) . ?
C17 C18 1.366(6) . ?
C17 H17 1.01(4) . ?
C18 C19 1.390(5) . ?
C18 H18 0.89(4) . ?
C19 C20 1.401(5) . ?
As1 F1 1.688(2) . ?
As1 F3 1.698(2) . ?
As1 F6 1.698(2) . ?
As1 F2 1.701(2) . ?
As1 F4 1.702(2) . ?
As1 F5 1.721(2) . ?
As2 F12 1.697(2) . ?
As2 F11 1.708(2) . ?
As2 F10 1.711(2) . ?
As2 F9 1.711(2) . ?
As2 F8 1.714(2) . ?
As2 F7 1.722(2) . ?
S20 O22 1.391(3) . ?
S20 O21 1.404(3) . ?
