#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:44:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180153 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/49/7104927.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_7104927
loop_
_publ_author_name
'Decken, Andreas'
'Mailman, Aaron'
'Passmore, Jack'
_publ_section_title
;
 The preparation of the MF6- (M = As, Sb) salts of 1,4-benzoquinodal
 bridged bis-1,3,2-dithiazolylium utilizing the cycloaddition and
 oxidative dehydrogenation chemistry of SNSMF6 and observation of a
 hybrid semiquinoidal-thiazyl radical-cation by EPR.
;
_journal_issue                   40
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6077
_journal_page_last               6079
_journal_paper_doi               10.1039/b910338d
_journal_year                    2009
_chemical_formula_moiety         'C6 H4 N O2 S2, C6 H4 O2, F6 Sb'
_chemical_formula_sum            'C12 H8 F6 N O4 S2 Sb'
_chemical_formula_weight         530.06
_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                 93.500(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0959(5)
_cell_length_b                   12.9028(7)
_cell_length_c                   14.3415(8)
_cell_measurement_reflns_used    6373
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      25.627
_cell_measurement_theta_min      2.582
_cell_volume                     1680.02(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(1)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker AXS SMART1000/P4'
_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  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8267
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.12
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              K760
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.973
_exptl_absorpt_correction_T_max  0.8271
_exptl_absorpt_correction_T_min  0.5058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            Black
_exptl_crystal_density_diffrn    2.096
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         2856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0203
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0282P)²+0.9181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0531
_refine_ls_wR_factor_ref         0.0539
_reflns_number_gt                2672
_reflns_number_total             2856
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            b910338d.txt
_cod_data_source_block           jp040304
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7104927
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 1.02599(7) 0.60533(5) 0.84936(5) 0.03351(16) Uani 1 1 d . . .
N N 1.0844(2) 0.66854(17) 0.76306(15) 0.0348(5) Uani 1 1 d . . .
S2 S 1.05456(8) 0.79026(5) 0.76268(4) 0.03221(15) Uani 1 1 d . . .
C3 C 0.9502(3) 0.70503(18) 0.90826(17) 0.0265(5) Uani 1 1 d . . .
C4 C 0.9657(3) 0.80032(19) 0.86343(16) 0.0248(5) Uani 1 1 d . . .
C5 C 0.9124(3) 0.89224(18) 0.90153(17) 0.0273(5) Uani 1 1 d . . .
C6 C 0.8423(3) 0.8831(2) 0.98323(18) 0.0303(5) Uani 1 1 d . . .
C7 C 0.8257(3) 0.7880(2) 1.02745(19) 0.0311(6) Uani 1 1 d . . .
C8 C 0.8781(3) 0.6978(2) 0.99179(18) 0.0298(5) Uani 1 1 d . . .
O1 O 0.8671(2) 0.60183(15) 1.02825(17) 0.0417(5) Uani 1 1 d . . .
O2 O 0.9364(2) 0.97991(15) 0.85306(14) 0.0374(5) Uani 1 1 d . . .
C11 C 0.3790(3) 0.44004(19) 0.79331(17) 0.0303(5) Uani 1 1 d . . .
C12 C 0.4580(3) 0.4189(2) 0.70893(19) 0.0384(6) Uani 1 1 d . . .
C13 C 0.5731(3) 0.4745(2) 0.68862(19) 0.0390(6) Uani 1 1 d . . .
C14 C 0.6295(3) 0.5589(2) 0.74994(18) 0.0355(6) Uani 1 1 d . . .
C15 C 0.5530(3) 0.5776(2) 0.83546(19) 0.0369(6) Uani 1 1 d . . .
C16 C 0.4370(3) 0.5222(2) 0.85601(18) 0.0328(6) Uani 1 1 d . . .
O3 O 0.2678(2) 0.39176(15) 0.80959(13) 0.0405(4) Uani 1 1 d . . .
O4 O 0.7370(2) 0.60955(18) 0.73140(14) 0.0516(5) Uani 1 1 d . . .
Sb Sb 0.353861(17) 0.768436(12) 0.048686(11) 0.02525(8) Uani 1 1 d . . .
F1 F 0.2228(2) 0.66146(16) 0.07372(14) 0.0600(5) Uani 1 1 d . . .
F2 F 0.4814(2) 0.87594(13) 0.02249(12) 0.0517(4) Uani 1 1 d . . .
F3 F 0.30307(19) 0.75499(13) -0.07907(11) 0.0412(4) Uani 1 1 d . . .
F4 F 0.1996(2) 0.86496(14) 0.05556(12) 0.0551(5) Uani 1 1 d . . .
F5 F 0.4018(2) 0.78365(14) 0.17593(11) 0.0514(5) Uani 1 1 d . . .
F6 F 0.50627(18) 0.67310(13) 0.03806(11) 0.0449(4) Uani 1 1 d . . .
H1 H 0.831(3) 0.603(2) 1.065(2) 0.024(9) Uiso 1 1 d . . .
H2 H 0.905(4) 1.024(3) 0.875(2) 0.053(11) Uiso 1 1 d . . .
H6 H 0.810(3) 0.939(2) 1.0101(18) 0.028(7) Uiso 1 1 d . . .
H7 H 0.779(3) 0.782(2) 1.080(2) 0.029(7) Uiso 1 1 d . . .
H12 H 0.426(3) 0.372(3) 0.674(2) 0.046(9) Uiso 1 1 d . . .
H13 H 0.621(3) 0.465(2) 0.6341(19) 0.040(8) Uiso 1 1 d . . .
H15 H 0.586(3) 0.630(2) 0.873(2) 0.045(8) Uiso 1 1 d . . .
H16 H 0.390(3) 0.531(2) 0.9074(19) 0.031(7) Uiso 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'
Sb Sb -0.5866 1.5461 '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
N S1 C3 99.32(12) . . ?
S2 N S1 116.14(13) . . ?
N S2 C4 99.31(12) . . ?
C4 C3 C8 121.1(2) . . ?
C4 C3 S1 112.31(19) . . ?
C8 C3 S1 126.6(2) . . ?
C3 C4 C5 121.1(2) . . ?
C3 C4 S2 112.93(18) . . ?
C5 C4 S2 125.98(19) . . ?
O2 C5 C6 127.5(2) . . ?
O2 C5 C4 115.8(2) . . ?
C6 C5 C4 116.7(2) . . ?
C5 C6 C7 122.2(2) . . ?
C5 C6 H6 119.5(17) . . ?
C7 C6 H6 118.3(17) . . ?
C8 C7 C6 121.9(2) . . ?
C8 C7 H7 116.2(17) . . ?
C6 C7 H7 121.9(17) . . ?
O1 C8 C7 126.8(2) . . ?
O1 C8 C3 116.2(2) . . ?
C7 C8 C3 117.0(2) . . ?
C8 O1 H1 111(3) . . ?
C5 O2 H2 111(3) . . ?
O3 C11 C16 121.4(2) . . ?
O3 C11 C12 121.0(2) . . ?
C16 C11 C12 117.6(2) . . ?
C13 C12 C11 121.1(3) . . ?
C13 C12 H12 121(2) . . ?
C11 C12 H12 118(2) . . ?
C12 C13 C14 121.6(3) . . ?
C12 C13 H13 122.3(18) . . ?
C14 C13 H13 116.1(18) . . ?
O4 C14 C15 121.4(3) . . ?
O4 C14 C13 121.4(3) . . ?
C15 C14 C13 117.1(2) . . ?
C16 C15 C14 121.5(3) . . ?
C16 C15 H15 120.7(19) . . ?
C14 C15 H15 117.7(19) . . ?
C15 C16 C11 121.1(2) . . ?
C15 C16 H16 123.6(18) . . ?
C11 C16 H16 115.3(18) . . ?
F5 Sb F2 90.44(8) . . ?
F5 Sb F6 91.08(8) . . ?
F2 Sb F6 89.97(8) . . ?
F5 Sb F3 178.96(7) . . ?
F2 Sb F3 89.49(8) . . ?
F6 Sb F3 89.95(7) . . ?
F5 Sb F1 90.20(8) . . ?
F2 Sb F1 178.95(8) . . ?
F6 Sb F1 90.84(9) . . ?
F3 Sb F1 89.85(8) . . ?
F5 Sb F4 90.55(8) . . ?
F2 Sb F4 89.61(9) . . ?
F6 Sb F4 178.32(7) . . ?
F3 Sb F4 88.42(7) . . ?
F1 Sb F4 89.56(9) . . ?
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 N 1.600(2) . ?
S1 C3 1.707(2) . ?
N S2 1.594(2) . ?
S2 C4 1.703(2) . ?
C3 C4 1.399(4) . ?
C3 C8 1.403(3) . ?
C4 C5 1.404(3) . ?
C5 O2 1.352(3) . ?
C5 C6 1.373(3) . ?
C6 C7 1.394(4) . ?
C6 H6 0.87(3) . ?
C7 C8 1.368(4) . ?
C7 H7 0.88(3) . ?
C8 O1 1.351(3) . ?
O1 H1 0.64(3) . ?
O2 H2 0.72(3) . ?
C11 O3 1.222(3) . ?
C11 C16 1.467(4) . ?
C11 C12 1.470(4) . ?
C12 C13 1.317(4) . ?
C12 H12 0.83(3) . ?
C13 C14 1.471(4) . ?
C13 H13 0.93(3) . ?
C14 O4 1.219(3) . ?
C14 C15 1.467(4) . ?
C15 C16 1.323(4) . ?
C15 H15 0.90(3) . ?
C16 H16 0.88(3) . ?
Sb F5 1.8606(16) . ?
Sb F2 1.8612(16) . ?
Sb F6 1.8665(15) . ?
Sb F3 1.8700(15) . ?
Sb F1 1.8729(17) . ?
Sb F4 1.8830(15) . ?
