#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/02/2220282.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2220282
loop_
_publ_author_name
'Wang, Ai-Rong'
_publ_section_title
;
 Bis[4-(2-nitrobenzenesulfonamido)pyridinium] hexafluorosilicate
;
_journal_coeditor_code           LX2077
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2405
_journal_paper_doi               10.1107/S1600536808038191
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '2C11 H10 N3 O4 S + , Si F6 2-'
_chemical_formula_moiety         '2C11 H10 N3 O4 S + , F6 Si 2-'
_chemical_formula_sum            'C22 H20 F6 N6 O8 S2 Si'
_chemical_formula_weight         702.65
_chemical_name_systematic
;
Bis[4-(2-nitrobenzenesulfonamido)pyridinium] hexafluorosilicate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.95(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.691(5)
_cell_length_b                   8.524(2)
_cell_length_c                   14.776(3)
_cell_measurement_reflns_used    3772
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.472
_cell_measurement_theta_min      1.922
_cell_volume                     2669.0(11)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10620
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.492
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0513P)²+1.0092P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                2456
_reflns_number_total             3064
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lx2077.cif
_cod_data_source_block           I
_cod_original_cell_volume        2669.0(10)
_cod_original_sg_symbol_Hall     -C_2yc
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2220282
_cod_database_fobs_code          2220282
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S 0.61983(2) 0.29097(5) 0.52758(4) 0.01969(15) Uani d . 1
O O1 0.58452(8) 0.32136(18) 0.42794(11) 0.0273(4) Uani d . 1
O O2 0.63133(8) 0.13308(16) 0.56235(12) 0.0282(4) Uani d . 1
O O3 0.69576(9) 0.3188(2) 0.75056(13) 0.0473(5) Uani d . 1
O O4 0.78705(10) 0.2230(3) 0.7737(2) 0.0843(10) Uani d . 1
N N1 0.56160(8) 0.8430(2) 0.63088(13) 0.0192(4) Uani d . 1
H H1N 0.5583(14) 0.942(3) 0.639(2) 0.052(9) Uiso d . 1
N N2 0.58416(9) 0.3725(2) 0.59405(14) 0.0194(4) Uani d . 1
H H2N 0.5795(14) 0.315(3) 0.628(2) 0.043(9) Uiso d . 1
N N3 0.74149(10) 0.3008(2) 0.72703(15) 0.0363(5) Uani d . 1
C C1 0.57577(9) 0.5317(2) 0.60418(14) 0.0167(4) Uani d . 1
C C2 0.57532(9) 0.6398(2) 0.53308(14) 0.0177(4) Uani d . 1
H H2 0.5800 0.6058 0.4748 0.021 Uiso calc R 1
C C3 0.56798(9) 0.7955(2) 0.54852(15) 0.0193(4) Uani d . 1
H H3 0.5674 0.8704 0.5006 0.023 Uiso calc R 1
C C4 0.56074(9) 0.7410(2) 0.70051(14) 0.0195(4) Uani d . 1
H H4 0.5555 0.7784 0.7577 0.023 Uiso calc R 1
C C5 0.56742(9) 0.5837(2) 0.68832(14) 0.0185(4) Uani d . 1
H H5 0.5664 0.5109 0.7364 0.022 Uiso calc R 1
C C6 0.69299(10) 0.3905(2) 0.55358(15) 0.0192(4) Uani d . 1
C C7 0.70103(11) 0.4743(2) 0.47788(16) 0.0258(5) Uani d . 1
H H7 0.6675 0.4795 0.4169 0.031 Uiso calc R 1
C C8 0.75749(12) 0.5503(3) 0.49066(18) 0.0309(5) Uani d . 1
H H8 0.7620 0.6078 0.4385 0.037 Uiso calc R 1
C C9 0.80672(11) 0.5435(3) 0.57748(19) 0.0307(5) Uani d . 1
H H9 0.8451 0.5965 0.5854 0.037 Uiso calc R 1
C C10 0.80059(10) 0.4591(3) 0.65379(18) 0.0295(5) Uani d . 1
H H10 0.8347 0.4530 0.7141 0.035 Uiso calc R 1
C C11 0.74405(10) 0.3839(3) 0.64084(16) 0.0249(5) Uani d . 1
Si Si 1.0000 0.65155(9) 0.7500 0.01731(19) Uani d S 1
F F1 0.94232(7) 0.64561(14) 0.79977(10) 0.0303(3) Uani d . 1
F F2 0.96119(6) 0.51233(14) 0.67115(9) 0.0265(3) Uani d . 1
F F3 0.96052(7) 0.79039(14) 0.67359(9) 0.0333(3) Uani d . 1
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'
Si Si 0.0817 0.0704 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O1 S O2 . . 120.30(10)
O1 S N2 . . 109.10(10)
O2 S N2 . . 104.47(10)
O1 S C6 . . 105.83(10)
O2 S C6 . . 109.54(10)
N2 S C6 . . 106.98(10)
C3 N1 C4 . . 122.20(18)
C3 N1 H1N . . 118(2)
C4 N1 H1N . . 120(2)
C1 N2 S . . 126.70(16)
C1 N2 H2N . . 122(2)
S N2 H2N . . 110(2)
O4 N3 O3 . . 123.2(2)
O4 N3 C11 . . 117.7(2)
O3 N3 C11 . . 119.09(19)
N2 C1 C2 . . 122.01(19)
N2 C1 C5 . . 118.34(18)
C2 C1 C5 . . 119.64(18)
C3 C2 C1 . . 118.97(19)
C3 C2 H2 . . 120.5
C1 C2 H2 . . 120.5
N1 C3 C2 . . 120.30(19)
N1 C3 H3 . . 119.8
C2 C3 H3 . . 119.8
N1 C4 C5 . . 119.82(19)
N1 C4 H4 . . 120.1
C5 C4 H4 . . 120.1
C4 C5 C1 . . 119.02(19)
C4 C5 H5 . . 120.5
C1 C5 H5 . . 120.5
C11 C6 C7 . . 117.3(2)
C11 C6 S . . 125.73(17)
C7 C6 S . . 116.81(16)
C8 C7 C6 . . 120.7(2)
C8 C7 H7 . . 119.7
C6 C7 H7 . . 119.7
C9 C8 C7 . . 120.8(2)
C9 C8 H8 . . 119.6
C7 C8 H8 . . 119.6
C8 C9 C10 . . 119.9(2)
C8 C9 H9 . . 120.0
C10 C9 H9 . . 120.0
C11 C10 C9 . . 119.0(2)
C11 C10 H10 . . 120.5
C9 C10 H10 . . 120.5
C10 C11 C6 . . 122.2(2)
C10 C11 N3 . . 115.0(2)
C6 C11 N3 . . 122.8(2)
F3 Si F3 2_756 . 89.03(10)
F3 Si F2 2_756 . 178.59(7)
F3 Si F2 . . 90.59(7)
F3 Si F2 2_756 2_756 90.59(7)
F3 Si F2 . 2_756 178.59(7)
F2 Si F2 . 2_756 89.82(9)
F3 Si F1 2_756 2_756 90.21(7)
F3 Si F1 . 2_756 92.20(7)
F2 Si F1 . 2_756 88.45(7)
F2 Si F1 2_756 2_756 89.16(7)
F3 Si F1 2_756 . 92.20(7)
F3 Si F1 . . 90.21(7)
F2 Si F1 . . 89.16(7)
F2 Si F1 2_756 . 88.45(7)
F1 Si F1 2_756 . 176.62(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S O1 . 1.426(2)
S O2 . 1.431(2)
S N2 . 1.634(2)
S C6 . 1.779(2)
O3 N3 . 1.216(3)
O4 N3 . 1.214(3)
N1 C3 . 1.338(3)
N1 C4 . 1.353(3)
N1 H1N . 0.86(3)
N2 C1 . 1.386(2)
N2 H2N . 0.73(3)
N3 C11 . 1.477(3)
C1 C2 . 1.395(3)
C1 C5 . 1.395(3)
C2 C3 . 1.367(3)
C2 H2 . 0.9500
C3 H3 . 0.9500
C4 C5 . 1.368(3)
C4 H4 . 0.9500
C5 H5 . 0.9500
C6 C11 . 1.393(3)
C6 C7 . 1.393(3)
C7 C8 . 1.387(3)
C7 H7 . 0.9500
C8 C9 . 1.368(3)
C8 H8 . 0.9500
C9 C10 . 1.385(3)
C9 H9 . 0.9500
C10 C11 . 1.385(3)
C10 H10 . 0.9500
Si F3 2_756 1.6597(14)
Si F3 . 1.6597(14)
Si F2 . 1.6756(13)
Si F2 2_756 1.6756(13)
Si F1 2_756 1.7161(13)
Si F1 . 1.7161(13)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N F1 4_656 0.86(3) 1.96(3) 2.789(2) 162(3)
N2 H2N F1 4_646 0.73(3) 1.97(3) 2.690(2) 171(3)
C4 H4 F2 4_656 0.95 2.35 3.141(2) 140.8
C5 H5 F3 4_646 0.95 2.50 3.426(3) 164.7
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
O1 S N2 C1 -65.8(2)
O2 S N2 C1 164.31(18)
C6 S N2 C1 48.2(2)
S N2 C1 C2 24.9(3)
S N2 C1 C5 -155.30(16)
N2 C1 C2 C3 -178.80(19)
C5 C1 C2 C3 1.4(3)
C4 N1 C3 C2 -1.5(3)
C1 C2 C3 N1 0.3(3)
C3 N1 C4 C5 0.9(3)
N1 C4 C5 C1 0.7(3)
N2 C1 C5 C4 178.30(18)
C2 C1 C5 C4 -1.9(3)
O1 S C6 C11 -175.15(18)
O2 S C6 C11 -44.1(2)
N2 S C6 C11 68.6(2)
O1 S C6 C7 0.70(18)
O2 S C6 C7 131.78(16)
N2 S C6 C7 -115.54(17)
C11 C6 C7 C8 -1.3(3)
S C6 C7 C8 -177.48(17)
C6 C7 C8 C9 0.6(3)
C7 C8 C9 C10 0.4(3)
C8 C9 C10 C11 -0.6(3)
C9 C10 C11 C6 -0.1(3)
C9 C10 C11 N3 -178.4(2)
C7 C6 C11 C10 1.0(3)
S C6 C11 C10 176.86(17)
C7 C6 C11 N3 179.2(2)
S C6 C11 N3 -5.0(3)
O4 N3 C11 C10 -43.6(3)
O3 N3 C11 C10 132.9(2)
O4 N3 C11 C6 138.1(3)
O3 N3 C11 C6 -45.4(3)
