#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/48/7104889.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_7104889
loop_
_publ_author_name
'Clarke, Caroline S.'
'Haynes, Delia A.'
'Rawson, Jeremy M.'
'Bond, Andrew D.'
_publ_section_title
;
 Small molecule fixation by a dithiadiazolyl radical: X-ray crystal structures
 of (CF3C6H3FCNSSN)2and (CF3C6H3FCNSSN)2˙G (G = N2, Ar, CO2and SO2)
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   22
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2774
_journal_page_last               2775
_journal_paper_doi               10.1039/b307509p
_journal_year                    2003
_chemical_formula_moiety         'C8 H3 F4 N2 S2, 0.26 SO2'
_chemical_formula_sum            'C8 H3 F4 N2 S2'
_chemical_formula_weight         267.24
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   17.1333(3)
_cell_length_b                   23.2358(4)
_cell_length_c                   10.6538(2)
_cell_measurement_reflns_used    15972
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.02
_cell_volume                     4241.34(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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     0.7107
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21236
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.529
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav Blessing (1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4847
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0519
_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)+(0.0758P)²+1.4460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1460
_reflns_number_gt                3449
_reflns_number_total             4847
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b307509p.txt
_cod_data_source_block           jr0250
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               7104889
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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
S11 S 0.60881(5) -0.04570(3) 0.67785(7) 0.0387(2) Uani 1 1 d . . .
S12 S 0.60252(4) -0.04589(3) 0.48138(7) 0.0365(2) Uani 1 1 d . . .
S21 S 0.78850(5) -0.04838(3) 0.65829(7) 0.0386(2) Uani 1 1 d . . .
S22 S 0.77884(5) -0.04577(3) 0.46312(7) 0.0393(2) Uani 1 1 d . . .
F23 F 0.76080(11) 0.23785(7) 0.37760(16) 0.0479(5) Uani 1 1 d . . .
F13 F 0.52519(10) 0.22774(7) 0.37220(16) 0.0475(4) Uani 1 1 d . . .
F241 F 0.85487(11) 0.31649(7) 0.68866(17) 0.0509(5) Uani 1 1 d . . .
F242 F 0.86871(11) 0.31724(7) 0.49027(18) 0.0526(5) Uani 1 1 d . . .
F243 F 0.75466(11) 0.32341(7) 0.5715(2) 0.0624(6) Uani 1 1 d . . .
F141 F 0.58806(12) 0.32422(7) 0.67759(18) 0.0557(5) Uani 1 1 d . . .
F142 F 0.59665(11) 0.32343(7) 0.47794(18) 0.0526(5) Uani 1 1 d . . .
F143 F 0.48495(10) 0.31146(8) 0.56662(19) 0.0580(5) Uani 1 1 d . . .
N21 N 0.79507(14) 0.02141(10) 0.6741(2) 0.0366(5) Uani 1 1 d . . .
N22 N 0.78341(15) 0.02458(10) 0.4545(2) 0.0368(5) Uani 1 1 d . . .
N11 N 0.60464(14) 0.02478(9) 0.6899(2) 0.0366(5) Uani 1 1 d . . .
N12 N 0.59643(14) 0.02443(9) 0.4696(2) 0.0337(5) Uani 1 1 d . . .
C14 C 0.57340(15) 0.23450(11) 0.5778(3) 0.0325(6) Uani 1 1 d . . .
C13 C 0.55470(15) 0.20105(11) 0.4737(2) 0.0323(6) Uani 1 1 d . . .
C26 C 0.83139(16) 0.13998(11) 0.6757(2) 0.0328(6) Uani 1 1 d . . .
H26 H 0.8468 0.1173 0.7457 0.039 Uiso 1 1 calc R . .
C22 C 0.77678(15) 0.14638(11) 0.4675(2) 0.0323(6) Uani 1 1 d . . .
H22 H 0.7564 0.1288 0.3939 0.039 Uiso 1 1 calc R . .
C27 C 0.82298(16) 0.29668(12) 0.5822(3) 0.0355(6) Uani 1 1 d . . .
C25 C 0.84037(15) 0.19921(11) 0.6795(2) 0.0324(6) Uani 1 1 d . . .
H25 H 0.8636 0.2168 0.7508 0.039 Uiso 1 1 calc R . .
C24 C 0.81547(14) 0.23323(11) 0.5792(2) 0.0282(5) Uani 1 1 d . . .
C23 C 0.78447(15) 0.20534(12) 0.4757(3) 0.0322(6) Uani 1 1 d . . .
C11 C 0.59076(15) 0.11499(10) 0.5792(2) 0.0286(5) Uani 1 1 d . . .
C16 C 0.60960(16) 0.14726(11) 0.6846(2) 0.0342(6) Uani 1 1 d . . .
H16 H 0.6282 0.1285 0.7581 0.041 Uiso 1 1 calc R . .
C17 C 0.56083(17) 0.29809(12) 0.5741(3) 0.0398(7) Uani 1 1 d . . .
C12 C 0.56325(15) 0.14251(11) 0.4720(2) 0.0323(6) Uani 1 1 d . . .
H12 H 0.5506 0.1210 0.3989 0.039 Uiso 1 1 calc R . .
C10 C 0.59823(16) 0.05157(11) 0.5802(2) 0.0315(6) Uani 1 1 d . . .
C20 C 0.79190(16) 0.05023(11) 0.5656(2) 0.0324(6) Uani 1 1 d . . .
C15 C 0.60143(16) 0.20659(12) 0.6834(3) 0.0376(6) Uani 1 1 d . . .
H15 H 0.6152 0.2283 0.7556 0.045 Uiso 1 1 calc R . .
C21 C 0.79975(14) 0.11344(11) 0.5697(2) 0.0279(5) 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'
F F 0.0171 0.0103 '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'
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
N11 S11 S12 94.45(9) . . ?
N12 S12 S11 94.46(8) . . ?
N21 S21 S22 94.55(9) . . ?
N22 S22 S21 94.64(9) . . ?
C20 N21 S21 113.90(19) . . ?
C20 N22 S22 113.68(19) . . ?
C10 N11 S11 113.68(19) . . ?
C10 N12 S12 113.60(19) . . ?
C15 C14 C13 117.8(2) . . ?
C15 C14 C17 122.3(2) . . ?
C13 C14 C17 119.9(2) . . ?
F13 C13 C12 119.2(2) . . ?
F13 C13 C14 118.0(2) . . ?
C12 C13 C14 122.7(2) . . ?
C25 C26 C21 120.3(2) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C23 C22 C21 118.1(2) . . ?
C23 C22 H22 121.0 . . ?
C21 C22 H22 121.0 . . ?
F243 C27 F241 105.7(2) . . ?
F243 C27 F242 106.6(2) . . ?
F241 C27 F242 104.9(2) . . ?
F243 C27 C24 112.8(2) . . ?
F241 C27 C24 113.3(2) . . ?
F242 C27 C24 112.9(2) . . ?
C26 C25 C24 120.4(2) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C23 C24 C25 117.5(2) . . ?
C23 C24 C27 121.1(2) . . ?
C25 C24 C27 121.4(2) . . ?
F23 C23 C22 118.5(2) . . ?
F23 C23 C24 118.0(2) . . ?
C22 C23 C24 123.6(2) . . ?
C16 C11 C12 119.7(2) . . ?
C16 C11 C10 120.8(2) . . ?
C12 C11 C10 119.6(2) . . ?
C15 C16 C11 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
F142 C17 F143 107.4(2) . . ?
F142 C17 F141 105.8(2) . . ?
F143 C17 F141 106.3(2) . . ?
F142 C17 C14 113.0(2) . . ?
F143 C17 C14 111.8(2) . . ?
F141 C17 C14 112.1(2) . . ?
C13 C12 C11 118.8(2) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
N11 C10 N12 123.8(2) . . ?
N11 C10 C11 118.7(2) . . ?
N12 C10 C11 117.5(2) . . ?
N22 C20 N21 123.2(2) . . ?
N22 C20 C21 118.8(2) . . ?
N21 C20 C21 118.0(2) . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C22 C21 C26 120.1(2) . . ?
C22 C21 C20 120.0(2) . . ?
C26 C21 C20 119.9(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
S11 N11 1.644(2) . ?
S11 S12 2.0959(10) . ?
S12 N12 1.642(2) . ?
S21 N21 1.634(2) . ?
S21 S22 2.0867(10) . ?
S22 N22 1.639(2) . ?
F23 C23 1.352(3) . ?
F13 C13 1.345(3) . ?
F241 C27 1.341(3) . ?
F242 C27 1.342(3) . ?
F243 C27 1.330(3) . ?
F141 C17 1.342(3) . ?
F142 C17 1.331(3) . ?
F143 C17 1.339(3) . ?
N21 C20 1.337(3) . ?
N22 C20 1.333(3) . ?
N11 C10 1.329(3) . ?
N12 C10 1.337(3) . ?
C14 C15 1.384(4) . ?
C14 C13 1.392(4) . ?
C14 C17 1.494(4) . ?
C13 C12 1.368(4) . ?
C26 C25 1.385(4) . ?
C26 C21 1.396(4) . ?
C26 H26 0.9500 . ?
C22 C23 1.379(4) . ?
C22 C21 1.389(4) . ?
C22 H22 0.9500 . ?
C27 C24 1.480(4) . ?
C25 C24 1.396(4) . ?
C25 H25 0.9500 . ?
C24 C23 1.384(4) . ?
C11 C16 1.389(4) . ?
C11 C12 1.391(4) . ?
C11 C10 1.479(3) . ?
C16 C15 1.386(4) . ?
C16 H16 0.9500 . ?
C12 H12 0.9500 . ?
C20 C21 1.475(3) . ?
C15 H15 0.9500 . ?
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
N11 S11 S12 N12 -0.70(12) . . . . ?
N21 S21 S22 N22 -0.49(13) . . . . ?
S22 S21 N21 C20 0.1(2) . . . . ?
S21 S22 N22 C20 0.9(2) . . . . ?
S12 S11 N11 C10 0.9(2) . . . . ?
S11 S12 N12 C10 0.4(2) . . . . ?
C15 C14 C13 F13 178.0(2) . . . . ?
C17 C14 C13 F13 -0.3(4) . . . . ?
C15 C14 C13 C12 -0.3(4) . . . . ?
C17 C14 C13 C12 -178.6(2) . . . . ?
C21 C26 C25 C24 2.2(4) . . . . ?
C26 C25 C24 C23 -2.2(4) . . . . ?
C26 C25 C24 C27 178.7(2) . . . . ?
F243 C27 C24 C23 60.6(3) . . . . ?
F241 C27 C24 C23 -179.3(2) . . . . ?
F242 C27 C24 C23 -60.2(3) . . . . ?
F243 C27 C24 C25 -120.3(3) . . . . ?
F241 C27 C24 C25 -0.3(4) . . . . ?
F242 C27 C24 C25 118.8(3) . . . . ?
C21 C22 C23 F23 -178.7(2) . . . . ?
C21 C22 C23 C24 1.6(4) . . . . ?
C25 C24 C23 F23 -179.4(2) . . . . ?
C27 C24 C23 F23 -0.4(4) . . . . ?
C25 C24 C23 C22 0.3(4) . . . . ?
C27 C24 C23 C22 179.4(2) . . . . ?
C12 C11 C16 C15 -0.3(4) . . . . ?
C10 C11 C16 C15 -179.1(2) . . . . ?
C15 C14 C17 F142 126.5(3) . . . . ?
C13 C14 C17 F142 -55.2(3) . . . . ?
C15 C14 C17 F143 -112.1(3) . . . . ?
C13 C14 C17 F143 66.1(3) . . . . ?
C15 C14 C17 F141 7.1(4) . . . . ?
C13 C14 C17 F141 -174.6(2) . . . . ?
F13 C13 C12 C11 -177.4(2) . . . . ?
C14 C13 C12 C11 0.9(4) . . . . ?
C16 C11 C12 C13 -0.6(4) . . . . ?
C10 C11 C12 C13 178.3(2) . . . . ?
S11 N11 C10 N12 -0.9(4) . . . . ?
S11 N11 C10 C11 177.57(19) . . . . ?
S12 N12 C10 N11 0.3(4) . . . . ?
S12 N12 C10 C11 -178.26(19) . . . . ?
C16 C11 C10 N11 16.2(4) . . . . ?
C12 C11 C10 N11 -162.7(2) . . . . ?
C16 C11 C10 N12 -165.2(2) . . . . ?
C12 C11 C10 N12 15.9(4) . . . . ?
S22 N22 C20 N21 -1.1(4) . . . . ?
S22 N22 C20 C21 177.7(2) . . . . ?
S21 N21 C20 N22 0.6(4) . . . . ?
S21 N21 C20 C21 -178.18(19) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C17 C14 C15 C16 177.6(2) . . . . ?
C11 C16 C15 C14 0.9(4) . . . . ?
C23 C22 C21 C26 -1.6(4) . . . . ?
C23 C22 C21 C20 179.4(2) . . . . ?
C25 C26 C21 C22 -0.3(4) . . . . ?
C25 C26 C21 C20 178.8(2) . . . . ?
N22 C20 C21 C22 18.1(4) . . . . ?
N21 C20 C21 C22 -163.0(3) . . . . ?
N22 C20 C21 C26 -160.9(3) . . . . ?
N21 C20 C21 C26 18.0(4) . . . . ?
