#------------------------------------------------------------------------------
#$Date: 2016-02-20 21:30:07 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/22/2222200.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_2222200
loop_
_publ_author_name
'Zhang, Chao-Yan'
'Gao, Qian'
'Cui, Yue'
'Xie, Ya-Bo'
_publ_section_title
;
 2,2'-[o-Phenylenebis(methylenethio)]bis(pyridine
 N-oxide)
;
_journal_coeditor_code           AT2798
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1482
_journal_paper_doi               10.1107/S160053680902073X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C18 H16 N2 O2 S2'
_chemical_formula_sum            'C18 H16 N2 O2 S2'
_chemical_formula_weight         356.47
_chemical_name_systematic
;
2,2'-[o-Phenylenebis(methylenethio)]bis(pyridine N-oxide)
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.20(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5075(15)
_cell_length_b                   17.810(4)
_cell_length_c                   12.480(3)
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.04
_cell_volume                     1610.3(7)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '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  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9681
_diffrn_reflns_theta_full        27.90
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0303
_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)+(0.0371P)²+0.5053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0830
_reflns_number_gt                3145
_reflns_number_total             3782
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            at2798.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2222200
_cod_database_fobs_code          2222200
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.17377(5) 0.17901(2) 0.34399(3) 0.03675(11) Uani d . 1 . .
S S2 -0.30419(5) -0.03050(2) -0.04963(3) 0.03289(10) Uani d . 1 . .
C C7 -0.00609(19) 0.04497(8) 0.25080(11) 0.0304(3) Uani d . 1 . .
N N1 -0.47078(17) -0.01887(7) -0.25627(10) 0.0350(3) Uani d . 1 . .
O O1 -0.48428(16) -0.09127(6) -0.24087(9) 0.0458(3) Uani d . 1 . .
C C14 -0.38096(18) 0.02425(8) -0.16810(11) 0.0308(3) Uani d . 1 . .
C C6 0.0423(2) 0.12465(8) 0.22786(12) 0.0335(3) Uani d . 1 . .
C C1 0.0008(2) 0.20710(8) 0.40531(11) 0.0324(3) Uani d . 1 . .
C C12 -0.11785(18) 0.00251(8) 0.16387(11) 0.0301(3) Uani d . 1 . .
C C15 -0.3632(2) 0.10057(9) -0.18273(13) 0.0397(3) Uani d . 1 . .
H H15A -0.3009 0.1304 -0.1235 0.048 Uiso calc R 1 . .
N N2 0.06622(19) 0.25129(7) 0.49662(10) 0.0402(3) Uani d . 1 . .
C C2 -0.1847(2) 0.18976(9) 0.37257(13) 0.0388(3) Uani d . 1 . .
H H2A -0.2299 0.1592 0.3111 0.047 Uiso calc R 1 . .
C C11 -0.1519(2) -0.07213(9) 0.18381(13) 0.0421(4) Uani d . 1 . .
H H11A -0.2260 -0.1007 0.1270 0.051 Uiso calc R 1 . .
C C13 -0.19734(19) 0.03928(8) 0.05228(11) 0.0318(3) Uani d . 1 . .
H H13A -0.0999 0.0646 0.0285 0.038 Uiso calc R 1 . .
H H13B -0.2883 0.0765 0.0587 0.038 Uiso calc R 1 . .
O O2 0.24350(18) 0.26652(7) 0.52668(10) 0.0570(3) Uani d . 1 . .
C C8 0.0643(2) 0.01115(9) 0.35310(12) 0.0402(3) Uani d . 1 . .
H H8A 0.1367 0.0392 0.4112 0.048 Uiso calc R 1 . .
C C9 0.0293(3) -0.06342(10) 0.37091(14) 0.0500(4) Uani d . 1 . .
H H9A 0.0787 -0.0852 0.4401 0.060 Uiso calc R 1 . .
C C18 -0.5444(2) 0.01241(10) -0.35676(13) 0.0456(4) Uani d . 1 . .
H H18A -0.6060 -0.0178 -0.4157 0.055 Uiso calc R 1 . .
C C5 -0.0505(3) 0.27874(9) 0.55340(14) 0.0536(5) Uani d . 1 . .
H H5A -0.0048 0.3091 0.6151 0.064 Uiso calc R 1 . .
C C3 -0.3033(3) 0.21749(10) 0.43040(16) 0.0511(4) Uani d . 1 . .
H H3A -0.4284 0.2060 0.4084 0.061 Uiso calc R 1 . .
C C17 -0.5296(3) 0.08746(11) -0.37289(14) 0.0527(4) Uani d . 1 . .
H H17A -0.5807 0.1085 -0.4424 0.063 Uiso calc R 1 . .
C C16 -0.4379(3) 0.13227(10) -0.28521(14) 0.0507(4) Uani d . 1 . .
H H16A -0.4269 0.1836 -0.2955 0.061 Uiso calc R 1 . .
C C10 -0.0783(3) -0.10491(10) 0.28622(14) 0.0512(4) Uani d . 1 . .
H H10A -0.1019 -0.1552 0.2975 0.061 Uiso calc R 1 . .
C C4 -0.2338(3) 0.26248(10) 0.52122(17) 0.0584(5) Uani d . 1 . .
H H4A -0.3125 0.2819 0.5608 0.070 Uiso calc R 1 . .
H H6A 0.125(2) 0.1237(9) 0.1798(14) 0.042(4) Uiso d . 1 . .
H H6B -0.062(2) 0.1528(10) 0.1903(14) 0.043(4) Uiso 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'
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
_geom_angle_publ_flag
C1 S1 C6 . . 101.12(7) ?
C14 S2 C13 . . 101.52(7) ?
C8 C7 C12 . . 118.93(13) ?
C8 C7 C6 . . 122.05(13) ?
C12 C7 C6 . . 118.93(12) ?
O1 N1 C18 . . 120.85(12) ?
O1 N1 C14 . . 118.39(12) ?
C18 N1 C14 . . 120.76(13) ?
N1 C14 C15 . . 119.39(13) ?
N1 C14 S2 . . 110.69(10) ?
C15 C14 S2 . . 129.92(11) ?
C7 C6 S1 . . 117.35(10) ?
C7 C6 H6A . . 109.0(10) ?
S1 C6 H6A . . 101.6(10) ?
C7 C6 H6B . . 112.7(10) ?
S1 C6 H6B . . 108.7(10) ?
H6A C6 H6B . . 106.4(14) ?
N2 C1 C2 . . 119.34(14) ?
N2 C1 S1 . . 112.67(11) ?
C2 C1 S1 . . 127.99(12) ?
C11 C12 C7 . . 118.52(13) ?
C11 C12 C13 . . 122.19(13) ?
C7 C12 C13 . . 119.29(12) ?
C16 C15 C14 . . 119.74(14) ?
C16 C15 H15A . . 120.1 ?
C14 C15 H15A . . 120.1 ?
O2 N2 C5 . . 121.49(14) ?
O2 N2 C1 . . 118.23(13) ?
C5 N2 C1 . . 120.27(14) ?
C3 C2 C1 . . 120.38(15) ?
C3 C2 H2A . . 119.8 ?
C1 C2 H2A . . 119.8 ?
C10 C11 C12 . . 121.50(15) ?
C10 C11 H11A . . 119.3 ?
C12 C11 H11A . . 119.3 ?
C12 C13 S2 . . 110.19(10) ?
C12 C13 H13A . . 109.6 ?
S2 C13 H13A . . 109.6 ?
C12 C13 H13B . . 109.6 ?
S2 C13 H13B . . 109.6 ?
H13A C13 H13B . . 108.1 ?
C9 C8 C7 . . 121.54(14) ?
C9 C8 H8A . . 119.2 ?
C7 C8 H8A . . 119.2 ?
C10 C9 C8 . . 119.57(15) ?
C10 C9 H9A . . 120.2 ?
C8 C9 H9A . . 120.2 ?
N1 C18 C17 . . 120.86(15) ?
N1 C18 H18A . . 119.6 ?
C17 C18 H18A . . 119.6 ?
N2 C5 C4 . . 120.81(16) ?
N2 C5 H5A . . 119.6 ?
C4 C5 H5A . . 119.6 ?
C4 C3 C2 . . 118.96(17) ?
C4 C3 H3A . . 120.5 ?
C2 C3 H3A . . 120.5 ?
C18 C17 C16 . . 119.52(16) ?
C18 C17 H17A . . 120.2 ?
C16 C17 H17A . . 120.2 ?
C15 C16 C17 . . 119.72(16) ?
C15 C16 H16A . . 120.1 ?
C17 C16 H16A . . 120.1 ?
C9 C10 C11 . . 119.92(15) ?
C9 C10 H10A . . 120.0 ?
C11 C10 H10A . . 120.0 ?
C5 C4 C3 . . 120.23(17) ?
C5 C4 H4A . . 119.9 ?
C3 C4 H4A . . 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 . 1.7442(15) ?
S1 C6 . 1.8061(15) ?
S2 C14 . 1.7384(15) ?
S2 C13 . 1.8084(14) ?
C7 C8 . 1.385(2) ?
C7 C12 . 1.4055(19) ?
C7 C6 . 1.511(2) ?
N1 O1 . 1.3116(16) ?
N1 C18 . 1.351(2) ?
N1 C14 . 1.3660(17) ?
C14 C15 . 1.383(2) ?
C6 H6A . 0.971(17) ?
C6 H6B . 0.942(18) ?
C1 N2 . 1.3658(18) ?
C1 C2 . 1.380(2) ?
C12 C11 . 1.389(2) ?
C12 C13 . 1.5128(19) ?
C15 C16 . 1.376(2) ?
C15 H15A . 0.9300 ?
N2 O2 . 1.3130(18) ?
N2 C5 . 1.355(2) ?
C2 C3 . 1.376(2) ?
C2 H2A . 0.9300 ?
C11 C10 . 1.382(2) ?
C11 H11A . 0.9300 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C8 C9 . 1.383(2) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.367(2) ?
C9 H9A . 0.9300 ?
C18 C17 . 1.361(3) ?
C18 H18A . 0.9300 ?
C5 C4 . 1.360(3) ?
C5 H5A . 0.9300 ?
C3 C4 . 1.374(3) ?
C3 H3A . 0.9300 ?
C17 C16 . 1.383(2) ?
C17 H17A . 0.9300 ?
C16 H16A . 0.9300 ?
C10 H10A . 0.9300 ?
C4 H4A . 0.9300 ?
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
_geom_hbond_publ_flag
C2 H2A O1 3_455 0.9300 2.4200 3.133(2) 134.00 yes
C5 H5A O1 2_455 0.9300 2.3800 3.253(2) 155.00 yes
C8 H8A S1 . 0.9300 2.6700 3.1105(18) 110.00 yes
C11 H11A S2 . 0.9300 2.4700 2.9322(18) 111.00 yes
C15 H15A O2 4_565 0.9300 2.5800 3.461(2) 158.00 yes
C9 H9A Cg2 3_556 0.93 2.90 3.645(2) 138 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 N1 C14 C15 . . . . 179.24(13) ?
C18 N1 C14 C15 . . . . -1.0(2) ?
O1 N1 C14 S2 . . . . -0.70(16) ?
C18 N1 C14 S2 . . . . 179.09(12) ?
C13 S2 C14 N1 . . . . -178.90(10) ?
C13 S2 C14 C15 . . . . 1.17(16) ?
C8 C7 C6 S1 . . . . -7.41(19) ?
C12 C7 C6 S1 . . . . 176.13(10) ?
C1 S1 C6 C7 . . . . -80.37(12) ?
C6 S1 C1 N2 . . . . -178.97(10) ?
C6 S1 C1 C2 . . . . 1.27(15) ?
C8 C7 C12 C11 . . . . -0.6(2) ?
C6 C7 C12 C11 . . . . 175.95(13) ?
C8 C7 C12 C13 . . . . 179.20(13) ?
C6 C7 C12 C13 . . . . -4.23(19) ?
N1 C14 C15 C16 . . . . 0.8(2) ?
S2 C14 C15 C16 . . . . -179.24(13) ?
C2 C1 N2 O2 . . . . 179.46(13) ?
S1 C1 N2 O2 . . . . -0.33(17) ?
C2 C1 N2 C5 . . . . -1.0(2) ?
S1 C1 N2 C5 . . . . 179.20(12) ?
N2 C1 C2 C3 . . . . 0.9(2) ?
S1 C1 C2 C3 . . . . -179.40(13) ?
C7 C12 C11 C10 . . . . -0.2(2) ?
C13 C12 C11 C10 . . . . 180.00(15) ?
C11 C12 C13 S2 . . . . -9.11(17) ?
C7 C12 C13 S2 . . . . 171.08(10) ?
C14 S2 C13 C12 . . . . -179.41(9) ?
C12 C7 C8 C9 . . . . 1.0(2) ?
C6 C7 C8 C9 . . . . -175.47(15) ?
C7 C8 C9 C10 . . . . -0.5(3) ?
O1 N1 C18 C17 . . . . -179.67(16) ?
C14 N1 C18 C17 . . . . 0.5(2) ?
O2 N2 C5 C4 . . . . 179.98(16) ?
C1 N2 C5 C4 . . . . 0.5(2) ?
C1 C2 C3 C4 . . . . -0.1(3) ?
N1 C18 C17 C16 . . . . 0.0(3) ?
C14 C15 C16 C17 . . . . -0.3(3) ?
C18 C17 C16 C15 . . . . -0.1(3) ?
C8 C9 C10 C11 . . . . -0.3(3) ?
C12 C11 C10 C9 . . . . 0.7(3) ?
N2 C5 C4 C3 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . -0.4(3) ?
