#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:51:18 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179350 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/47/4324790.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_4324790
loop_
_publ_author_name
'Alexander Yu. Makarov'
'Vladimir V. Zhivonitko'
'Arkady G. Makarov'
'Samat B. Zikirin'
'Irina Yu. Bagryanskaya'
'Victor A. Bagryansky'
'Yuri V. Gatilov'
'Irina G. Irtegova'
'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
;
 Interaction of 1,3,2,4-Benzodithiadiazines and Their 1-Se Congeners with
 Ph3P and Some Properties of the Iminophosphorane Products
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3017
_journal_page_last               3027
_journal_paper_doi               10.1021/ic102565x
_journal_volume                  50
_journal_year                    2011
_chemical_formula_moiety         'C12 H2 F8 N2 S4'
_chemical_formula_sum            'C12 H2 F8 N2 S4'
_chemical_formula_weight         454.40
_chemical_melting_point          479
_chemical_name_systematic
; 
 1,2,3,4,8,9,10,11-octafluoro-7',14'-
 dibenzo[d,i][1,2,6,7,3,8]tetrathiadiazecine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 111.330(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.166(3)
_cell_length_b                   5.3890(10)
_cell_length_c                   12.325(3)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.767
_cell_measurement_theta_min      22.538
_cell_volume                     752.7(3)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker XSCANS'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(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  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            1799
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        -3.17
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  0.9579
_exptl_absorpt_correction_T_min  0.5038
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.005
_exptl_crystal_description       plate-needle
_exptl_crystal_F_000             448
_exptl_crystal_recrystallization_method chloroform
_exptl_crystal_size_max          1.1
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.066
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0609P)²+0.0831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                1313
_reflns_number_total             1722
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic102565x_si_001_8.cif
_cod_data_source_block           zvota_compound_10
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4324790
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
S1 S 0.94119(5) 0.07056(15) 0.30117(6) 0.0423(2) Uani 1 1 d
S2 S 0.86617(5) 0.33742(14) 0.37261(6) 0.0419(2) Uani 1 1 d
F3 F 1.35329(13) -0.1548(4) 0.59156(16) 0.0552(5) Uani 1 1 d
F5 F 1.32015(16) 0.5500(4) 0.35925(16) 0.0565(5) Uani 1 1 d
F4 F 1.45229(13) 0.2362(4) 0.52729(15) 0.0556(5) Uani 1 1 d
C6 C 1.1502(2) 0.3172(5) 0.3401(2) 0.0360(6) Uani 1 1 d
F6 F 1.08679(14) 0.4780(4) 0.25720(14) 0.0523(5) Uani 1 1 d
C1 C 1.0948(2) 0.1229(5) 0.3727(2) 0.0333(5) Uani 1 1 d
C2 C 1.16305(19) -0.0408(5) 0.4606(2) 0.0331(5) Uani 1 1 d
N8 N 0.88782(19) 0.2524(5) 0.5099(2) 0.0389(5) Uani 1 1 d
C4 C 1.3363(2) 0.1996(6) 0.4780(2) 0.0385(6) Uani 1 1 d
C5 C 1.2691(2) 0.3584(5) 0.3919(2) 0.0368(6) Uani 1 1 d
C3 C 1.2843(2) 0.0033(5) 0.5115(2) 0.0372(6) Uani 1 1 d
H1N H 0.957(3) 0.275(5) 0.556(2) 0.039(8) Uiso 1 1 d
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 0.0301(3) 0.0551(5) 0.0355(3) -0.0061(3) 0.0046(2) -0.0089(3)
S2 0.0296(3) 0.0413(4) 0.0526(4) 0.0123(3) 0.0125(3) 0.0018(3)
F3 0.0324(8) 0.0602(12) 0.0655(11) 0.0229(9) 0.0088(7) 0.0022(7)
F5 0.0497(9) 0.0637(12) 0.0564(11) 0.0118(9) 0.0196(8) -0.0182(9)
F4 0.0257(7) 0.0732(13) 0.0629(11) 0.0079(10) 0.0101(7) -0.0130(8)
C6 0.0348(12) 0.0432(15) 0.0295(12) -0.0029(11) 0.0110(10) -0.0020(11)
F6 0.0474(9) 0.0602(12) 0.0415(9) 0.0140(8) 0.0069(7) -0.0017(8)
C1 0.0295(11) 0.0408(15) 0.0301(12) -0.0076(11) 0.0114(9) -0.0043(10)
C2 0.0283(11) 0.0362(14) 0.0365(12) -0.0044(11) 0.0138(10) -0.0041(10)
N8 0.0317(11) 0.0377(13) 0.0466(13) -0.0057(10) 0.0135(9) -0.0087(10)
C4 0.0263(11) 0.0490(17) 0.0400(13) -0.0017(12) 0.0117(10) -0.0046(10)
C5 0.0346(12) 0.0431(15) 0.0352(13) -0.0026(12) 0.0157(10) -0.0106(11)
C3 0.0288(11) 0.0420(15) 0.0403(14) 0.0044(12) 0.0121(10) -0.0008(10)
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'
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'
H H 0.0000 0.0000 '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
C1 S1 S2 103.10(9) . .
N8 S2 S1 107.95(9) . .
F6 C6 C5 117.7(2) . .
F6 C6 C1 120.2(2) . .
C5 C6 C1 122.1(2) . .
C6 C1 C2 119.0(2) . .
C6 C1 S1 120.8(2) . .
C2 C1 S1 120.11(19) . .
C3 C2 N8 120.9(2) . 3_756
C3 C2 C1 118.0(2) . .
N8 C2 C1 120.9(2) 3_756 .
C2 N8 S2 123.97(18) 3_756 .
F4 C4 C3 120.4(2) . .
F4 C4 C5 119.5(2) . .
C3 C4 C5 120.1(2) . .
F5 C5 C6 120.7(2) . .
F5 C5 C4 120.0(2) . .
C6 C5 C4 119.3(2) . .
F3 C3 C4 118.5(2) . .
F3 C3 C2 119.9(2) . .
C4 C3 C2 121.6(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.775(2) .
S1 S2 2.0642(11) .
S2 N8 1.679(2) .
F3 C3 1.343(3) .
F5 C5 1.340(3) .
F4 C4 1.332(3) .
C6 F6 1.348(3) .
C6 C5 1.371(3) .
C6 C1 1.382(4) .
C1 C2 1.410(4) .
C2 C3 1.397(3) .
C2 N8 1.407(3) 3_756
N8 C2 1.407(3) 3_756
C4 C3 1.372(4) .
C4 C5 1.377(4) .
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_4
C1 S1 S2 N8 -72.56(13) . .
F6 C6 C1 C2 -179.2(2) . .
C5 C6 C1 C2 -1.1(4) . .
F6 C6 C1 S1 3.4(3) . .
C5 C6 C1 S1 -178.4(2) . .
S2 S1 C1 C6 -77.4(2) . .
S2 S1 C1 C2 105.3(2) . .
C6 C1 C2 C3 0.5(4) . .
S1 C1 C2 C3 177.83(19) . .
C6 C1 C2 N8 -174.8(2) . 3_756
S1 C1 C2 N8 2.5(3) . 3_756
S1 S2 N8 C2 -65.8(2) . 3_756
F6 C6 C5 F5 -1.1(4) . .
C1 C6 C5 F5 -179.3(2) . .
F6 C6 C5 C4 179.2(2) . .
C1 C6 C5 C4 1.0(4) . .
F4 C4 C5 F5 -0.8(4) . .
C3 C4 C5 F5 180.0(2) . .
F4 C4 C5 C6 178.9(2) . .
C3 C4 C5 C6 -0.3(4) . .
F4 C4 C3 F3 -2.4(4) . .
C5 C4 C3 F3 176.7(3) . .
F4 C4 C3 C2 -179.5(2) . .
C5 C4 C3 C2 -0.3(4) . .
N8 C2 C3 F3 -1.5(4) 3_756 .
C1 C2 C3 F3 -176.8(2) . .
N8 C2 C3 C4 175.5(2) 3_756 .
C1 C2 C3 C4 0.2(4) . .
