#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:14:58 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179445 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/42/4334286.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_4334286
loop_
_publ_author_name
'Alexander Yu. Makarov'
'Frank Blockhuys'
'Irina Yu. Bagryanskaya'
'Yuri V. Gatilov'
'Makhmut M. Shakirov'
'Andrey V. Zibarev'
_publ_contact_author_email       bagryan@nioch.nsc.ru
_publ_contact_author_name        'Dr. I. Yu. Bagryanskaya'
_publ_section_title
;
 Experimental and Computational Study on the Structure and Properties of
 Herz Cations and Radicals: 1,2,3-Benzodithiazolium,
 1,2,3-Benzodithiazolyl, and Their Se Congeners
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3699
_journal_page_last               3710
_journal_paper_doi               10.1021/ic302203t
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C6 H4 N S Se 1+, B F4 1-'
_chemical_formula_sum            'C6 H4 B F4 N S Se'
_chemical_formula_weight         287.93
_chemical_melting_point          428
_chemical_name_systematic
; 
 2,1,3-benzothiaselenazolium tetrafluoroborate 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 91.68(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.769(4)
_cell_length_b                   5.6552(15)
_cell_length_c                   21.781(5)
_cell_measurement_reflns_used    46
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      12.46
_cell_measurement_theta_min      4.80
_cell_volume                     1818.4(8)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      193(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '2θ/ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1342
_diffrn_reflns_av_sigmaI/netI    0.0853
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            1997
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.76
_diffrn_standards_decay_%        1.5
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.376
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.32
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            dark_orange
_exptl_crystal_density_diffrn    2.104
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1299
_refine_ls_R_factor_gt           0.0709
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0889P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1613
_refine_ls_wR_factor_ref         0.1914
_reflns_number_gt                1173
_reflns_number_total             1982
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic302203t_si_001_5.cif
_cod_data_source_block           zm416
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_database_code               4334286
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Se1 Se 0.58459(5) 0.24985(18) 0.43583(4) 0.0402(3) Uani 1 1 d . . .
S2 S 0.65268(15) -0.0139(4) 0.49212(11) 0.0423(6) Uani 1 1 d . . .
C7A C 0.6159(5) 0.0737(15) 0.3686(4) 0.0321(19) Uani 1 1 d . . .
N3 N 0.6855(4) -0.1893(12) 0.4406(3) 0.0363(17) Uani 1 1 d . . .
C6 C 0.6216(5) -0.0096(18) 0.2622(4) 0.045(2) Uani 1 1 d . . .
H6A H 0.6075 0.0299 0.2206 0.053 Uiso 1 1 calc R . .
C3A C 0.6658(5) -0.1366(15) 0.3823(4) 0.0307(18) Uani 1 1 d . . .
C4 C 0.6944(5) -0.2827(16) 0.3346(4) 0.037(2) Uani 1 1 d . . .
H4A H 0.7288 -0.4214 0.3430 0.044 Uiso 1 1 calc R . .
C7 C 0.5938(5) 0.1357(16) 0.3067(4) 0.0338(19) Uani 1 1 d . . .
H7A H 0.5606 0.2753 0.2971 0.041 Uiso 1 1 calc R . .
C5 C 0.6711(6) -0.2193(16) 0.2749(4) 0.041(2) Uani 1 1 d . . .
H5A H 0.6885 -0.3178 0.2420 0.049 Uiso 1 1 calc R . .
B B 0.4013(6) 0.6102(18) 0.3913(6) 0.039(2) Uani 1 1 d . . .
F1 F 0.3264(3) 0.7367(10) 0.3731(3) 0.0568(15) Uani 1 1 d . A .
F2 F 0.4669(8) 0.763(2) 0.4113(12) 0.139(8) Uani 0.74(2) 1 d P A 1
F3 F 0.3813(6) 0.491(2) 0.4437(5) 0.097(5) Uani 0.74(2) 1 d P A 1
F4 F 0.4290(12) 0.463(4) 0.3490(6) 0.152(10) Uani 0.74(2) 1 d P A 1
F2' F 0.3860(17) 0.382(5) 0.3969(15) 0.062(9) Uiso 0.26(2) 1 d P A 2
F3' F 0.454(2) 0.699(5) 0.4343(11) 0.042(8) Uiso 0.26(2) 1 d P A 2
F4' F 0.4629(19) 0.624(6) 0.3443(14) 0.058(8) Uiso 0.26(2) 1 d P A 2
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
Se1 0.0304(4) 0.0358(5) 0.0544(6) -0.0051(5) 0.0019(3) 0.0095(4)
S2 0.0350(11) 0.0443(13) 0.0477(12) -0.0020(11) 0.0050(9) 0.0123(11)
C7A 0.013(3) 0.035(4) 0.049(5) -0.006(4) 0.009(3) -0.005(3)
N3 0.028(3) 0.038(4) 0.043(4) 0.004(3) 0.006(3) 0.003(3)
C6 0.030(4) 0.063(6) 0.042(5) 0.011(5) 0.005(3) 0.002(5)
C3A 0.013(3) 0.037(4) 0.043(5) 0.000(4) 0.013(3) -0.001(3)
C4 0.016(3) 0.043(6) 0.053(5) -0.010(4) 0.007(3) -0.001(4)
C7 0.017(4) 0.035(5) 0.049(5) 0.004(4) 0.003(3) -0.001(4)
C5 0.029(4) 0.048(6) 0.046(5) 0.001(5) 0.010(3) 0.003(4)
B 0.018(4) 0.029(5) 0.069(7) 0.001(5) 0.000(4) -0.001(4)
F1 0.040(3) 0.065(4) 0.065(3) 0.006(3) 0.004(2) 0.023(3)
F2 0.044(6) 0.076(9) 0.30(2) 0.024(11) -0.019(9) -0.031(6)
F3 0.075(7) 0.129(10) 0.089(9) 0.064(8) 0.037(5) 0.026(7)
F4 0.169(15) 0.196(19) 0.089(9) -0.089(11) -0.046(10) 0.154(16)
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'
B B 0.0013 0.0007 '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'
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'
Se Se -0.0929 2.2259 '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
C7A Se1 S2 87.4(3)
N3 S2 Se1 100.2(3)
C7 C7A C3A 120.4(7)
C7 C7A Se1 124.4(6)
C3A C7A Se1 115.2(6)
C3A N3 S2 118.3(6)
C7 C6 C5 122.5(8)
C7 C6 H6A 118.7
C5 C6 H6A 118.7
N3 C3A C4 120.9(8)
N3 C3A C7A 119.0(7)
C4 C3A C7A 120.1(8)
C5 C4 C3A 118.2(8)
C5 C4 H4A 120.9
C3A C4 H4A 120.9
C6 C7 C7A 117.9(8)
C6 C7 H7A 121.1
C7A C7 H7A 121.1
C4 C5 C6 120.9(8)
C4 C5 H5A 119.5
C6 C5 H5A 119.5
F3' B F2' 114(2)
F3' B F4 123.9(16)
F2' B F4 60.1(14)
F3' B F2 28.2(12)
F2' B F2 135.7(16)
F4 B F2 113.1(13)
F3' B F3 74.1(13)
F2' B F3 53.0(14)
F4 B F3 110.6(12)
F2 B F3 102.4(14)
F3' B F1 117.8(15)
F2' B F1 113.7(14)
F4 B F1 113.3(10)
F2 B F1 108.8(9)
F3 B F1 107.9(8)
F3' B F4' 96.8(17)
F2' B F4' 103.9(18)
F4 B F4' 45.4(12)
F2 B F4' 74.0(14)
F3 B F4' 143.6(15)
F1 B F4' 107.4(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se1 C7A 1.840(8)
Se1 S2 2.161(3)
S2 N3 1.584(7)
C7A C7 1.422(12)
C7A C3A 1.426(11)
N3 C3A 1.329(11)
C6 C7 1.344(12)
C6 C5 1.416(12)
C6 H6A 0.9500
C3A C4 1.403(12)
C4 C5 1.382(13)
C4 H4A 0.9500
C7 H7A 0.9500
C5 H5A 0.9500
B F3' 1.30(3)
B F2' 1.32(3)
B F4 1.316(14)
B F2 1.361(15)
B F3 1.365(14)
B F1 1.365(11)
B F4' 1.39(3)
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
C7A Se1 S2 N3 -0.2(3)
S2 Se1 C7A C7 -179.7(6)
S2 Se1 C7A C3A 0.1(5)
Se1 S2 N3 C3A 0.3(6)
S2 N3 C3A C4 178.8(6)
S2 N3 C3A C7A -0.3(10)
C7 C7A C3A N3 179.8(7)
Se1 C7A C3A N3 0.1(9)
C7 C7A C3A C4 0.7(11)
Se1 C7A C3A C4 -179.0(6)
N3 C3A C4 C5 179.5(7)
C7A C3A C4 C5 -1.4(11)
C5 C6 C7 C7A 0.2(12)
C3A C7A C7 C6 -0.1(11)
Se1 C7A C7 C6 179.7(6)
C3A C4 C5 C6 1.5(12)
C7 C6 C5 C4 -0.9(13)
