#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:24:00 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179244 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/64/4316464.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_4316464
loop_
_publ_author_name
'Caleb D. Martin'
'Paul J. Ragogna'
_publ_contact_author_address
;
Department of Chemistry, The University of Western Ontario, 
The Chemistry Building, 1151 Richmond Street, London, Ontario N6A 5B7, Canada
;
_publ_contact_author_email       pragogna@uwo.ca
_publ_contact_author_fax         1-519-661-3022
_publ_contact_author_name        'Paul J. Ragogna'
_publ_contact_author_phone       1-519-661-2111x87048
_publ_section_title
;
 Synthesis and Reactivity of Sulfur(II) Dications Stabilized Using
 Monodentate Ligands
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8164
_journal_page_last               8172
_journal_paper_doi               10.1021/ic1012582
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C24 H18 F6 N2 O6 S3'
_chemical_formula_weight         640.58
_chemical_name_systematic
; 
 ? 
;
_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                 104.2900(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.234(3)
_cell_length_b                   9.8706(13)
_cell_length_c                   11.2571(15)
_cell_measurement_reflns_used    10737
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.0854
_cell_measurement_theta_min      0.929694
_cell_volume                     2717.1(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      173(2)
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12084
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_T_max  0.9320
_exptl_absorpt_correction_T_min  0.8416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker 2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_refine_diff_density_max         .517
_refine_diff_density_min         -.387
_refine_diff_density_rms         .113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.283
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.283
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0596
_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)+(0.0802P)²+2.6186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1497
_refine_ls_wR_factor_ref         0.1657
_reflns_number_gt                1912
_reflns_number_total             2394
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic1012582_si_002_1.cif
_cod_data_source_block           5Ph
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4316464
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
S2 S 0.10347(4) 0.19450(10) 0.93559(8) 0.0250(3) Uani 1 1 d . . .
S1 S 0.0000 -0.02797(14) 0.7500 0.0321(4) Uani 1 2 d S . .
C12 C -0.19370(15) -0.3040(4) 0.3035(3) 0.0286(9) Uani 1 1 d . . .
H12A H -0.1706 -0.2438 0.2737 0.034 Uiso 1 1 calc R . .
N1 N -0.04785(12) -0.1407(3) 0.6667(3) 0.0246(7) Uani 1 1 d . . .
O2 O 0.07615(12) 0.1193(3) 1.0119(2) 0.0390(7) Uani 1 1 d . . .
O1 O 0.09115(12) 0.1481(3) 0.8115(2) 0.0421(8) Uani 1 1 d . . .
C11 C -0.18116(14) -0.3378(4) 0.4277(3) 0.0238(8) Uani 1 1 d . . .
C6 C -0.09107(15) -0.1814(4) 0.7093(3) 0.0273(9) Uani 1 1 d . . .
H6A H -0.0919 -0.1619 0.7914 0.033 Uiso 1 1 calc R . .
C4 C -0.13383(14) -0.2756(3) 0.5124(3) 0.0213(8) Uani 1 1 d . . .
C2 C -0.04608(15) -0.1679(4) 0.5495(3) 0.0255(8) Uani 1 1 d . . .
H2A H -0.0154 -0.1401 0.5209 0.031 Uiso 1 1 calc R . .
C5 C -0.13305(15) -0.2496(4) 0.6354(3) 0.0282(9) Uani 1 1 d . . .
H5A H -0.1624 -0.2803 0.6673 0.034 Uiso 1 1 calc R . .
C13 C -0.23944(15) -0.3572(4) 0.2239(4) 0.0335(10) Uani 1 1 d . . .
H13A H -0.2484 -0.3310 0.1401 0.040 Uiso 1 1 calc R . .
O3 O 0.15952(12) 0.2254(4) 0.9876(3) 0.0536(9) Uani 1 1 d . . .
C3 C -0.08789(14) -0.2346(4) 0.4729(3) 0.0246(8) Uani 1 1 d . . .
H3A H -0.0860 -0.2537 0.3914 0.030 Uiso 1 1 calc R . .
C16 C -0.21466(15) -0.4294(4) 0.4686(4) 0.0357(10) Uani 1 1 d . . .
H16A H -0.2067 -0.4535 0.5529 0.043 Uiso 1 1 calc R . .
C15 C -0.25938(17) -0.4856(5) 0.3873(4) 0.0453(12) Uani 1 1 d . . .
H15A H -0.2815 -0.5501 0.4153 0.054 Uiso 1 1 calc R . .
C14 C -0.27201(16) -0.4479(4) 0.2653(4) 0.0387(11) Uani 1 1 d . . .
H14A H -0.3033 -0.4849 0.2100 0.046 Uiso 1 1 calc R . .
F3 F 0.08786(12) 0.4417(3) 0.8508(3) 0.0674(9) Uani 1 1 d . . .
F2 F 0.08044(15) 0.4180(3) 1.0350(3) 0.0782(10) Uani 1 1 d . . .
F1 F 0.01653(11) 0.3473(3) 0.8842(3) 0.0749(10) Uani 1 1 d . . .
C20 C 0.07059(18) 0.3597(5) 0.9261(5) 0.0448(11) 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F .0171 .0103 '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
O3 S2 O1 115.13(19) . . ?
O3 S2 O2 116.11(19) . . ?
O1 S2 O2 113.52(18) . . ?
O3 S2 C20 103.0(2) . . ?
O1 S2 C20 104.1(2) . . ?
O2 S2 C20 102.67(19) . . ?
N1 S1 N1 100.3(2) . 2_556 ?
N1 S1 O1 160.14(11) . . ?
N1 S1 O1 81.18(12) 2_556 . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C6 N1 C2 120.5(3) . . ?
C6 N1 S1 120.8(2) . . ?
C2 N1 S1 117.8(2) . . ?
S2 O1 S1 113.78(15) . . ?
C16 C11 C12 118.8(3) . . ?
C16 C11 C4 121.4(3) . . ?
C12 C11 C4 119.9(3) . . ?
C5 C6 N1 120.4(3) . . ?
C5 C6 H6A 119.8 . . ?
N1 C6 H6A 119.8 . . ?
C3 C4 C5 116.7(3) . . ?
C3 C4 C11 121.4(3) . . ?
C5 C4 C11 121.9(3) . . ?
C3 C2 N1 120.4(3) . . ?
C3 C2 H2A 119.8 . . ?
N1 C2 H2A 119.8 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C15 C16 C11 120.3(4) . . ?
C15 C16 H16A 119.8 . . ?
C11 C16 H16A 119.8 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C13 C14 C15 120.2(4) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
F2 C20 F3 108.2(4) . . ?
F2 C20 F1 108.1(4) . . ?
F3 C20 F1 107.4(4) . . ?
F2 C20 S2 110.9(3) . . ?
F3 C20 S2 111.6(3) . . ?
F1 C20 S2 110.5(3) . . ?
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
S2 O3 1.424(3) . ?
S2 O1 1.430(3) . ?
S2 O2 1.434(3) . ?
S2 C20 1.821(5) . ?
S1 N1 1.737(3) . ?
S1 N1 1.737(3) 2_556 ?
S1 O1 2.829(3) . ?
C12 C13 1.379(5) . ?
C12 C11 1.395(5) . ?
C12 H12A 0.9500 . ?
N1 C6 1.356(5) . ?
N1 C2 1.359(4) . ?
C11 C16 1.392(5) . ?
C11 C4 1.466(5) . ?
C6 C5 1.354(5) . ?
C6 H6A 0.9500 . ?
C4 C3 1.400(5) . ?
C4 C5 1.404(5) . ?
C2 C3 1.356(5) . ?
C2 H2A 0.9500 . ?
C5 H5A 0.9500 . ?
C13 C14 1.373(6) . ?
C13 H13A 0.9500 . ?
C3 H3A 0.9500 . ?
C16 C15 1.381(6) . ?
C16 H16A 0.9500 . ?
C15 C14 1.382(6) . ?
C15 H15A 0.9500 . ?
C14 H14A 0.9500 . ?
F3 C20 1.321(5) . ?
F2 C20 1.321(6) . ?
F1 C20 1.334(5) . ?
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
N1 S1 N1 C6 92.8(3) 2_556 . . . ?
O1 S1 N1 C6 -174.6(3) . . . . ?
N1 S1 N1 C2 -98.5(3) 2_556 . . . ?
O1 S1 N1 C2 -5.9(6) . . . . ?
O3 S2 O1 S1 151.18(19) . . . . ?
O2 S2 O1 S1 13.9(2) . . . . ?
C20 S2 O1 S1 -96.9(2) . . . . ?
N1 S1 O1 S2 -172.2(3) . . . . ?
N1 S1 O1 S2 -76.2(2) 2_556 . . . ?
C13 C12 C11 C16 2.0(6) . . . . ?
C13 C12 C11 C4 -177.2(3) . . . . ?
C2 N1 C6 C5 0.0(5) . . . . ?
S1 N1 C6 C5 168.4(3) . . . . ?
C16 C11 C4 C3 151.5(4) . . . . ?
C12 C11 C4 C3 -29.4(5) . . . . ?
C16 C11 C4 C5 -31.0(5) . . . . ?
C12 C11 C4 C5 148.2(4) . . . . ?
C6 N1 C2 C3 0.9(5) . . . . ?
S1 N1 C2 C3 -167.9(3) . . . . ?
N1 C6 C5 C4 -2.3(6) . . . . ?
C3 C4 C5 C6 3.6(5) . . . . ?
C11 C4 C5 C6 -174.1(4) . . . . ?
C11 C12 C13 C14 -2.3(6) . . . . ?
N1 C2 C3 C4 0.6(6) . . . . ?
C5 C4 C3 C2 -2.7(5) . . . . ?
C11 C4 C3 C2 175.0(3) . . . . ?
C12 C11 C16 C15 0.1(6) . . . . ?
C4 C11 C16 C15 179.3(4) . . . . ?
C11 C16 C15 C14 -1.9(7) . . . . ?
C12 C13 C14 C15 0.5(6) . . . . ?
C16 C15 C14 C13 1.6(7) . . . . ?
O3 S2 C20 F2 -57.0(4) . . . . ?
O1 S2 C20 F2 -177.5(3) . . . . ?
O2 S2 C20 F2 63.9(3) . . . . ?
O3 S2 C20 F3 63.7(4) . . . . ?
O1 S2 C20 F3 -56.8(4) . . . . ?
O2 S2 C20 F3 -175.3(3) . . . . ?
O3 S2 C20 F1 -176.8(3) . . . . ?
O1 S2 C20 F1 62.7(4) . . . . ?
O2 S2 C20 F1 -55.9(4) . . . . ?
