#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/30/2233068.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_2233068
loop_
_publ_author_name
'Arman, Hadi D.'
'Kaulgud, Trupta'
'Tiekink, Edward R. T.'
_publ_section_title
;
 2-Aminobenzoic acid--4-(pyridin-4-yldisulfanyl)pyridine (1/1)
;
_journal_coeditor_code           ZS2162
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3361
_journal_paper_doi               10.1107/S1600536811048483
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C7 H7 N O2, C10 H8 N2 S2'
_chemical_formula_moiety         'C7 H7 N O2, C10 H8 N2 S2'
_chemical_formula_sum            'C17 H15 N3 O2 S2'
_chemical_formula_weight         357.46
_chemical_name_systematic
;
2-Aminobenzoic acid--4-(pyridin-4-yldisulfanyl)pyridine (1/1)
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 103.218(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.636(2)
_cell_length_b                   12.728(3)
_cell_length_c                   15.688(4)
_cell_measurement_reflns_used    3807
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      40.5
_cell_measurement_theta_min      2.7
_cell_volume                     1678.7(7)
_computing_cell_refinement
'CrystalClear (Molecular Structure Corporation & Rigaku, 2005)'
_computing_data_collection
'CrystalClear (Molecular Structure Corporation & Rigaku, 2005)'
_computing_data_reduction
'CrystalClear (Molecular Structure Corporation & Rigaku, 2005)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      98(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku AFC12Κ/SATURN724 CCD'
_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  0.000
_diffrn_reflns_av_sigmaI/netI    0.032
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3149
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.7
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.232
_refine_ls_abs_structure_details nd
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0305
_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)+(0.0470P)²+0.5616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0780
_reflns_number_gt                3115
_reflns_number_total             3149
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2162.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2233068
_cod_database_fobs_code          2233068
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'
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_symmetry_multiplicity
S S1 1.03842(6) 0.51910(4) 0.54403(3) 0.02643(12) Uani d . 1 1
S S2 0.84697(6) 0.53636(3) 0.44236(3) 0.02623(12) Uani d . 1 1
O O1 0.4176(2) 0.28720(11) 0.58052(9) 0.0301(3) Uani d D 1 1
H H1o 0.425(4) 0.2527(19) 0.6269(10) 0.045 Uiso d D 1 1
O O2 0.45445(19) 0.42702(12) 0.66806(9) 0.0311(3) Uani d . 1 1
N N1 0.4410(2) 0.30644(14) 0.41463(11) 0.0323(4) Uani d D 1 1
H H1n 0.428(3) 0.2877(17) 0.3594(5) 0.048 Uiso d D 1 1
H H2n 0.418(4) 0.2615(14) 0.4525(11) 0.048 Uiso d D 1 1
N N2 0.9169(2) 0.27383(14) 0.73043(12) 0.0302(4) Uani d . 1 1
N N3 0.9212(2) 0.33036(13) 0.21812(11) 0.0271(3) Uani d . 1 1
C C1 0.4350(2) 0.41116(14) 0.43227(12) 0.0212(4) Uani d . 1 1
C C2 0.4369(2) 0.45314(14) 0.51627(12) 0.0213(4) Uani d . 1 1
C C3 0.4360(2) 0.56293(16) 0.52675(13) 0.0261(4) Uani d . 1 1
H H3 0.4382 0.5912 0.5831 0.031 Uiso calc R 1 1
C C4 0.4322(3) 0.63068(16) 0.45784(15) 0.0291(4) Uani d . 1 1
H H4 0.4322 0.7046 0.4665 0.035 Uiso calc R 1 1
C C5 0.4282(3) 0.58886(16) 0.37511(14) 0.0276(4) Uani d . 1 1
H H5 0.4246 0.6347 0.3269 0.033 Uiso calc R 1 1
C C6 0.4294(2) 0.48188(15) 0.36270(13) 0.0241(4) Uani d . 1 1
H H6 0.4263 0.4551 0.3058 0.029 Uiso calc R 1 1
C C7 0.4379(2) 0.38954(15) 0.59532(12) 0.0240(4) Uani d . 1 1
C C8 1.0466(3) 0.33503(17) 0.75021(13) 0.0309(4) Uani d . 1 1
H H8 1.1159 0.3276 0.8064 0.037 Uiso calc R 1 1
C C9 1.0850(3) 0.40835(17) 0.69325(13) 0.0284(4) Uani d . 1 1
H H9 1.1792 0.4492 0.7096 0.034 Uiso calc R 1 1
C C10 0.9828(2) 0.42076(14) 0.61162(12) 0.0221(4) Uani d . 1 1
C C11 0.8478(2) 0.35789(15) 0.58888(13) 0.0236(4) Uani d . 1 1
H H11 0.7764 0.3636 0.5332 0.028 Uiso calc R 1 1
C C12 0.8218(2) 0.28615(15) 0.65130(13) 0.0269(4) Uani d . 1 1
H H12 0.7298 0.2430 0.6363 0.032 Uiso calc R 1 1
C C13 0.8862(2) 0.45427(14) 0.35820(12) 0.0213(4) Uani d . 1 1
C C14 1.0171(2) 0.38876(15) 0.36659(13) 0.0246(4) Uani d . 1 1
H H14 1.0959 0.3849 0.4198 0.030 Uiso calc R 1 1
C C15 1.0288(3) 0.32873(16) 0.29402(14) 0.0268(4) Uani d . 1 1
H H15 1.1186 0.2841 0.2989 0.032 Uiso calc R 1 1
C C16 0.7979(3) 0.39530(17) 0.21060(13) 0.0293(4) Uani d . 1 1
H H16 0.7221 0.3981 0.1562 0.035 Uiso calc R 1 1
C C17 0.7749(3) 0.45889(16) 0.27830(13) 0.0264(4) Uani d . 1 1
H H17 0.6857 0.5045 0.2705 0.032 Uiso calc R 1 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
C10 S1 S2 105.22(7)
C13 S2 S1 105.12(7)
C7 O1 H1o 112(2)
C1 N1 H1n 117.5(15)
C1 N1 H2n 118.2(15)
H1n N1 H2n 119.4(18)
C12 N2 C8 116.85(18)
C16 N3 C15 117.96(17)
N1 C1 C6 117.63(17)
N1 C1 C2 124.29(18)
C6 C1 C2 118.07(17)
C3 C2 C1 118.91(17)
C3 C2 C7 116.40(16)
C1 C2 C7 124.69(17)
C4 C3 C2 121.99(18)
C4 C3 H3 119.0
C2 C3 H3 119.0
C3 C4 C5 118.82(18)
C3 C4 H4 120.6
C5 C4 H4 120.6
C6 C5 C4 120.63(18)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C1 121.56(18)
C5 C6 H6 119.2
C1 C6 H6 119.2
O2 C7 O1 122.14(18)
O2 C7 C2 123.34(18)
O1 C7 C2 114.52(16)
N2 C8 C9 123.6(2)
N2 C8 H8 118.2
C9 C8 H8 118.2
C8 C9 C10 118.5(2)
C8 C9 H9 120.8
C10 C9 H9 120.8
C9 C10 C11 119.33(18)
C9 C10 S1 115.41(15)
C11 C10 S1 125.26(16)
C10 C11 C12 117.17(19)
C10 C11 H11 121.4
C12 C11 H11 121.4
N2 C12 C11 124.59(19)
N2 C12 H12 117.7
C11 C12 H12 117.7
C14 C13 C17 119.32(17)
C14 C13 S2 124.98(16)
C17 C13 S2 115.70(15)
C13 C14 C15 117.50(19)
C13 C14 H14 121.2
C15 C14 H14 121.3
N3 C15 C14 123.7(2)
N3 C15 H15 118.1
C14 C15 H15 118.1
N3 C16 C17 123.1(2)
N3 C16 H16 118.4
C17 C16 H16 118.4
C16 C17 C13 118.30(19)
C16 C17 H17 120.8
C13 C17 H17 120.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C10 1.7762(19)
S1 S2 2.0297(8)
S2 C13 1.7761(18)
O1 C7 1.328(2)
O1 H1o 0.8399(10)
O2 C7 1.215(2)
N1 C1 1.365(2)
N1 H1n 0.8800(11)
N1 H2n 0.8801(10)
N2 C12 1.332(3)
N2 C8 1.341(3)
N3 C16 1.332(3)
N3 C15 1.332(3)
C1 C6 1.407(3)
C1 C2 1.418(2)
C2 C3 1.407(3)
C2 C7 1.479(2)
C3 C4 1.377(3)
C3 H3 0.9500
C4 C5 1.396(3)
C4 H4 0.9500
C5 C6 1.376(3)
C5 H5 0.9500
C6 H6 0.9500
C8 C9 1.384(3)
C8 H8 0.9500
C9 C10 1.388(3)
C9 H9 0.9500
C10 C11 1.391(3)
C11 C12 1.394(3)
C11 H11 0.9500
C12 H12 0.9500
C13 C14 1.387(3)
C13 C17 1.396(3)
C14 C15 1.394(3)
C14 H14 0.9500
C15 H15 0.9500
C16 C17 1.385(3)
C16 H16 0.9500
C17 H17 0.9500
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 H2n O1 . 0.88(2) 2.036(18) 2.667(2) 127.9(15)
N1 H1n N2 4_454 0.881(10) 2.151(12) 3.027(3) 172.8(19)
O1 H1o N3 4_455 0.840(18) 1.79(2) 2.621(2) 173(3)
C17 H17 O2 2_564 0.95 2.42 3.251(3) 146
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 C13 -95.20(9)
N1 C1 C2 C3 177.7(2)
C6 C1 C2 C3 -1.1(3)
N1 C1 C2 C7 -3.1(3)
C6 C1 C2 C7 178.12(18)
C1 C2 C3 C4 0.5(3)
C7 C2 C3 C4 -178.81(18)
C2 C3 C4 C5 0.3(3)
C3 C4 C5 C6 -0.5(3)
C4 C5 C6 C1 -0.2(3)
N1 C1 C6 C5 -177.9(2)
C2 C1 C6 C5 1.0(3)
C3 C2 C7 O2 -7.8(3)
C1 C2 C7 O2 172.92(19)
C3 C2 C7 O1 171.55(19)
C1 C2 C7 O1 -7.7(3)
C12 N2 C8 C9 -0.2(3)
N2 C8 C9 C10 1.1(3)
C8 C9 C10 C11 -1.5(3)
C8 C9 C10 S1 178.27(16)
S2 S1 C10 C9 -169.32(13)
S2 S1 C10 C11 10.46(18)
C9 C10 C11 C12 1.1(3)
S1 C10 C11 C12 -178.70(14)
C8 N2 C12 C11 -0.3(3)
C10 C11 C12 N2 -0.1(3)
S1 S2 C13 C14 3.90(18)
S1 S2 C13 C17 -175.51(13)
C17 C13 C14 C15 -1.2(3)
S2 C13 C14 C15 179.40(15)
C16 N3 C15 C14 1.9(3)
C13 C14 C15 N3 -0.6(3)
C15 N3 C16 C17 -1.5(3)
N3 C16 C17 C13 -0.2(3)
C14 C13 C17 C16 1.6(3)
S2 C13 C17 C16 -178.97(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657297
