#------------------------------------------------------------------------------
#$Date: 2016-08-06 09:35:02 +0300 (Sat, 06 Aug 2016) $
#$Revision: 185071 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/02/7040223.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_7040223
loop_
_publ_author_name
'Smithson, Chad S.'
'MacDonald, Daniel J.'
'Matt Letvenuk, T.'
'Carello, Christian E.'
'Jennings, Michael'
'Lough, Alan J.'
'Britten, James'
'Decken, Andreas'
'Preuss, Kathryn E.'
_publ_section_title
;
 A 1,2,3-dithiazolyl-o-naphthoquinone: a neutral radical with isolable
 cation and anion oxidation states.
;
_journal_issue                   23
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9608
_journal_page_last               9620
_journal_paper_doi               10.1039/c6dt01249c
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C10 H4 N O2 S2, C F3 O3 S'
_chemical_formula_sum            'C11 H4 F3 N O5 S3'
_chemical_formula_weight         383.33
_chemical_name_systematic
'4,5-dioxo-naphtho[1,2-d][1,2,3]dithiazol-2-ium triflate'
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-03-30 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.0537(17)
_cell_length_b                   6.4960(6)
_cell_length_c                   25.224(3)
_cell_measurement_reflns_used    2618
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.78
_cell_measurement_theta_min      2.39
_cell_volume                     2794.3(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            27184
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.590
_exptl_absorpt_correction_T_max  0.9941
_exptl_absorpt_correction_T_min  0.8336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1536
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0341
_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)+(0.0311P)²+2.3899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0782
_reflns_number_gt                1854
_reflns_number_total             2462
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c6dt01249c2.cif
_cod_data_source_block           chad3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               7040223
_solvent_exptl_crystal_recrystallization_method 'acetonitrile and toluene'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
S1 S 0.12317(4) 0.43491(10) 0.52714(3) 0.02153(18) Uani 1 1 d .
S2 S 0.06048(4) 0.66376(10) 0.56053(3) 0.02352(18) Uani 1 1 d .
N1 N 0.06150(14) 0.5869(3) 0.62027(9) 0.0237(5) Uani 1 1 d .
C1 C 0.09948(16) 0.4104(4) 0.62901(11) 0.0191(6) Uani 1 1 d .
C2 C 0.10464(16) 0.3231(4) 0.68287(11) 0.0210(6) Uani 1 1 d .
C3 C 0.07415(17) 0.4276(4) 0.72566(11) 0.0297(7) Uani 1 1 d .
H3A H 0.0499 0.5578 0.7206 0.036 Uiso 1 1 calc R
C4 C 0.0788(2) 0.3439(5) 0.77568(13) 0.0371(8) Uani 1 1 d .
H4A H 0.0569 0.4154 0.8050 0.045 Uiso 1 1 calc R
C5 C 0.1153(2) 0.1552(5) 0.78341(13) 0.0388(8) Uani 1 1 d .
H5A H 0.1187 0.0985 0.8181 0.047 Uiso 1 1 calc R
C6 C 0.14658(19) 0.0505(4) 0.74126(12) 0.0312(7) Uani 1 1 d .
H6A H 0.1718 -0.0781 0.7468 0.037 Uiso 1 1 calc R
C7 C 0.14140(16) 0.1324(4) 0.69028(11) 0.0224(6) Uani 1 1 d .
C8 C 0.17641(16) 0.0188(4) 0.64588(11) 0.0227(6) Uani 1 1 d .
O1 O 0.20681(12) -0.1499(3) 0.65005(8) 0.0303(5) Uani 1 1 d .
C9 C 0.17693(16) 0.1181(4) 0.59005(11) 0.0213(6) Uani 1 1 d .
O2 O 0.20956(11) 0.0355(3) 0.55364(8) 0.0276(5) Uani 1 1 d .
C10 C 0.13421(15) 0.3161(4) 0.58539(11) 0.0195(6) Uani 1 1 d .
O3 O 0.05692(12) 0.6959(3) 0.45276(8) 0.0295(5) Uani 1 1 d .
O4 O 0.01019(11) 0.9640(3) 0.39409(7) 0.0266(5) Uani 1 1 d .
O5 O 0.08069(12) 1.0536(3) 0.47443(8) 0.0307(5) Uani 1 1 d .
S3 S 0.06642(4) 0.90434(10) 0.43390(3) 0.02088(18) Uani 1 1 d .
C11 C 0.15906(19) 0.8907(5) 0.39907(13) 0.0362(8) Uani 1 1 d .
F1 F 0.17784(12) 1.0726(3) 0.37816(8) 0.0560(6) Uani 1 1 d .
F2 F 0.21632(11) 0.8353(3) 0.43148(8) 0.0545(6) Uani 1 1 d .
F3 F 0.15634(12) 0.7557(3) 0.35923(8) 0.0601(6) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C10 S1 S2 91.90(10)
N1 S2 S1 99.14(9)
C1 N1 S2 115.60(19)
N1 C1 C10 117.0(2)
N1 C1 C2 120.7(2)
C10 C1 C2 122.3(2)
C3 C2 C7 120.0(3)
C3 C2 C1 120.7(2)
C7 C2 C1 119.3(2)
C4 C3 C2 120.1(3)
C4 C3 H3A 119.9
C2 C3 H3A 119.9
C3 C4 C5 120.2(3)
C3 C4 H4A 119.9
C5 C4 H4A 119.9
C6 C5 C4 120.2(3)
C6 C5 H5A 119.9
C4 C5 H5A 119.9
C5 C6 C7 120.1(3)
C5 C6 H6A 119.9
C7 C6 H6A 119.9
C6 C7 C2 119.3(3)
C6 C7 C8 119.1(2)
C2 C7 C8 121.6(2)
O1 C8 C7 124.0(3)
O1 C8 C9 116.8(3)
C7 C8 C9 119.1(2)
O2 C9 C10 123.7(3)
O2 C9 C8 120.8(2)
C10 C9 C8 115.5(2)
C1 C10 C9 121.9(2)
C1 C10 S1 116.4(2)
C9 C10 S1 121.7(2)
O5 S3 O4 115.41(11)
O5 S3 O3 114.79(12)
O4 S3 O3 114.00(12)
O5 S3 C11 103.40(14)
O4 S3 C11 104.81(14)
O3 S3 C11 102.24(14)
F2 C11 F1 108.0(3)
F2 C11 F3 108.2(3)
F1 C11 F3 107.0(3)
F2 C11 S3 110.9(2)
F1 C11 S3 111.0(2)
F3 C11 S3 111.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C10 1.670(3)
S1 S2 2.0155(10)
S2 N1 1.587(2)
N1 C1 1.336(3)
C1 C10 1.391(4)
C1 C2 1.475(4)
C2 C3 1.377(4)
C2 C7 1.401(4)
C3 C4 1.376(4)
C3 H3A 0.9500
C4 C5 1.389(4)
C4 H4A 0.9500
C5 C6 1.370(4)
C5 H5A 0.9500
C6 C7 1.394(4)
C6 H6A 0.9500
C7 C8 1.468(4)
C8 O1 1.217(3)
C8 C9 1.549(4)
C9 O2 1.200(3)
C9 C10 1.483(4)
O3 S3 1.4441(19)
O4 S3 1.4416(19)
O5 S3 1.4297(19)
S3 C11 1.810(3)
C11 F2 1.324(4)
C11 F1 1.333(4)
C11 F3 1.335(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
C10 S1 S2 N1 0.08(13)
S1 S2 N1 C1 -0.4(2)
S2 N1 C1 C10 0.7(3)
S2 N1 C1 C2 179.9(2)
N1 C1 C2 C3 -3.6(4)
C10 C1 C2 C3 175.6(3)
N1 C1 C2 C7 176.7(2)
C10 C1 C2 C7 -4.1(4)
C7 C2 C3 C4 -0.8(4)
C1 C2 C3 C4 179.5(3)
C2 C3 C4 C5 1.0(5)
C3 C4 C5 C6 -0.4(5)
C4 C5 C6 C7 -0.4(5)
C5 C6 C7 C2 0.6(4)
C5 C6 C7 C8 179.1(3)
C3 C2 C7 C6 0.0(4)
C1 C2 C7 C6 179.7(3)
C3 C2 C7 C8 -178.4(3)
C1 C2 C7 C8 1.2(4)
C6 C7 C8 O1 3.9(4)
C2 C7 C8 O1 -177.7(3)
C6 C7 C8 C9 -174.9(3)
C2 C7 C8 C9 3.6(4)
O1 C8 C9 O2 -3.7(4)
C7 C8 C9 O2 175.1(3)
O1 C8 C9 C10 175.5(2)
C7 C8 C9 C10 -5.6(3)
N1 C1 C10 C9 -179.1(2)
C2 C1 C10 C9 1.7(4)
N1 C1 C10 S1 -0.6(3)
C2 C1 C10 S1 -179.8(2)
O2 C9 C10 C1 -177.7(3)
C8 C9 C10 C1 3.1(4)
O2 C9 C10 S1 3.9(4)
C8 C9 C10 S1 -175.30(19)
S2 S1 C10 C1 0.3(2)
S2 S1 C10 C9 178.7(2)
O5 S3 C11 F2 59.2(2)
O4 S3 C11 F2 -179.5(2)
O3 S3 C11 F2 -60.3(2)
O5 S3 C11 F1 -60.9(2)
O4 S3 C11 F1 60.4(2)
O3 S3 C11 F1 179.6(2)
O5 S3 C11 F3 179.9(2)
O4 S3 C11 F3 -58.9(3)
O3 S3 C11 F3 60.3(3)
