#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:58:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178414 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/35/4023509.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_4023509
loop_
_publ_author_name
'Teresa Olszewska'
'Maria Gdaniec'
'Tadeusz Połoński'
_publ_section_title
;
 Enantiomeric Resolution of N,N'-Dimethyldithiodianthranilide
 through Diastereomeric Silver(I) Complex. Circular Dichroism
 Spectra, Racemization Barrier, and Molecular Self-Assembly
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4859
_journal_page_last               4864
_journal_paper_doi               10.1021/jo8004809
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         '2(C16 H14 N2 S2), C7 H8'
_chemical_formula_sum            'C39 H36 N4 S4'
_chemical_formula_weight         688.96
_chemical_name_systematic
; 
5,11-dimethyldibenzo[b,f][1,5]diazocine-6,12(5H,11H)-dithione 
toluene 2:1 solvate 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2008-02-14 # Formatted by publCIF
;
_cell_angle_alpha                107.36(2)
_cell_angle_beta                 95.120(10)
_cell_angle_gamma                101.21(2)
_cell_formula_units_Z            1
_cell_length_a                   8.5694(8)
_cell_length_b                   9.811(2)
_cell_length_c                   11.707(2)
_cell_measurement_reflns_used    45
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      7
_cell_volume                     910.0(3)
_computing_cell_refinement       'Kuma KM-4 software (Kuma Diffraction, 1991)'
_computing_data_collection       'Kuma KM-4 sofware (Kuma Diffraction, 1991)'
_computing_data_reduction        'Kuma KM-4 software (Kuma Diffraction, 1991)'
_computing_molecular_graphics
; Stereochemical Workstation (Siemens, 1989).
Mercury, Version 1.4
(Macrae et al., 2006)
;
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device       'KM-4 four-circle diffractometer'
_diffrn_measurement_method       'ω/2θ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3030
_diffrn_reflns_theta_full        65.09
_diffrn_reflns_theta_max         65.09
_diffrn_reflns_theta_min         4.01
_diffrn_standards_decay_%        1.5%
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.648
_exptl_absorpt_correction_T_max  0.868
_exptl_absorpt_correction_T_min  0.433
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0115(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3030
_refine_ls_number_restraints     59
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0761P)²+0.4729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1503
_reflns_number_gt                2445
_reflns_number_total             3030
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo8004809-File006.cif
_cod_data_source_block           (+-)-2b-toluene
_cod_database_code               4023509
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.74039(14) 0.23726(11) 1.08988(7) 0.0924(4) Uani 1 1 d . . .
S2 S 1.11678(10) 0.04914(10) 0.74544(7) 0.0762(3) Uani 1 1 d . . .
N1 N 0.9608(2) 0.2613(2) 0.8093(2) 0.0544(6) Uani 1 1 d . . .
N2 N 0.7069(3) 0.0358(2) 0.8750(2) 0.0600(6) Uani 1 1 d . . .
C1 C 0.8201(3) 0.3198(3) 0.8094(2) 0.0493(6) Uani 1 1 d . . .
C2 C 0.6977(3) 0.2781(3) 0.8713(2) 0.0505(6) Uani 1 1 d . . .
C3 C 0.5682(3) 0.3438(3) 0.8757(3) 0.0638(7) Uani 1 1 d . . .
H3 H 0.4861 0.3178 0.9174 0.077 Uiso 1 1 calc R . .
C4 C 0.5593(4) 0.4466(4) 0.8192(3) 0.0739(9) Uani 1 1 d . . .
H4 H 0.4712 0.4892 0.8224 0.089 Uiso 1 1 calc R . .
C5 C 0.6799(4) 0.4865(3) 0.7580(3) 0.0723(8) Uani 1 1 d . . .
H5 H 0.6731 0.5561 0.7197 0.087 Uiso 1 1 calc R . .
C6 C 0.8110(4) 0.4244(3) 0.7530(3) 0.0615(7) Uani 1 1 d . . .
H6 H 0.8931 0.4524 0.7119 0.074 Uiso 1 1 calc R . .
C7 C 0.7133(3) 0.1743(3) 0.9399(2) 0.0561(7) Uani 1 1 d . . .
C8 C 0.6774(3) -0.0145(3) 0.7443(2) 0.0563(7) Uani 1 1 d . . .
C9 C 0.7976(3) 0.0281(3) 0.6817(2) 0.0529(6) Uani 1 1 d . . .
C10 C 0.7690(4) -0.0251(3) 0.5558(2) 0.0634(8) Uani 1 1 d . . .
H10 H 0.8474 0.0031 0.5120 0.076 Uiso 1 1 calc R . .
C11 C 0.6242(4) -0.1196(4) 0.4959(3) 0.0739(9) Uani 1 1 d . . .
H11 H 0.6054 -0.1546 0.4116 0.089 Uiso 1 1 calc R . .
C12 C 0.5077(5) -0.1627(4) 0.5590(3) 0.0809(10) Uani 1 1 d . . .
H12 H 0.4112 -0.2278 0.5176 0.097 Uiso 1 1 calc R . .
C13 C 0.5332(4) -0.1097(3) 0.6842(3) 0.0733(9) Uani 1 1 d . . .
H13 H 0.4540 -0.1379 0.7273 0.088 Uiso 1 1 calc R . .
C14 C 0.9583(3) 0.1216(3) 0.7487(2) 0.0523(6) Uani 1 1 d . . .
C15 C 1.1099(4) 0.3621(4) 0.8828(4) 0.0838(10) Uani 1 1 d . . .
H15A H 1.1241 0.3487 0.9607 0.126 Uiso 1 1 calc R . .
H15B H 1.1033 0.4616 0.8932 0.126 Uiso 1 1 calc R . .
H15C H 1.1998 0.3421 0.8427 0.126 Uiso 1 1 calc R . .
C16 C 0.7300(5) -0.0747(4) 0.9330(3) 0.0899(11) Uani 1 1 d . . .
H16A H 0.7904 -0.0263 1.0129 0.135 Uiso 1 1 calc R . .
H16B H 0.7876 -0.1399 0.8856 0.135 Uiso 1 1 calc R . .
H16C H 0.6269 -0.1299 0.9383 0.135 Uiso 1 1 calc R . .
C1T C 0.8746(6) 0.5019(7) 0.4572(5) 0.076(2) Uani 0.50 1 d PDU . .
C2T C 0.9717(9) 0.6277(7) 0.5451(6) 0.083(2) Uani 0.50 1 d PDU . .
H2TA H 0.9370 0.7179 0.5695 0.100 Uiso 0.50 1 d PR . .
C3T C 1.1212(8) 0.6203(11) 0.5974(7) 0.098(4) Uani 0.50 1 d PDU . .
H3TA H 1.1891 0.7057 0.6576 0.117 Uiso 0.50 1 d PR . .
C4T C 1.1750(8) 0.4919(13) 0.5642(9) 0.118(4) Uani 0.50 1 d PDU . .
H4TA H 1.2782 0.4878 0.6007 0.142 Uiso 0.50 1 d PR . .
C5T C 1.0781(10) 0.3664(10) 0.4765(9) 0.110(4) Uani 0.50 1 d PDU . .
H5TA H 1.1130 0.2762 0.4522 0.132 Uiso 0.50 1 d PR . .
C6T C 0.9285(8) 0.3739(7) 0.4243(6) 0.0561(16) Uani 0.50 1 d PDU . .
H6TA H 0.8607 0.2885 0.3641 0.067 Uiso 0.50 1 d PR . .
C7T C 0.7150(8) 0.5144(12) 0.4034(8) 0.125(3) Uani 0.50 1 d PDU . .
H7TA H 0.6614 0.4212 0.3452 0.188 Uiso 0.50 1 d PR . .
H7TB H 0.6504 0.5407 0.4658 0.188 Uiso 0.50 1 d PR . .
H7TC H 0.7305 0.5878 0.3639 0.188 Uiso 0.50 1 d PR . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C14 N1 C1 122.7(2) . . ?
C14 N1 C15 120.8(2) . . ?
C1 N1 C15 116.5(2) . . ?
C7 N2 C8 122.0(2) . . ?
C7 N2 C16 121.7(2) . . ?
C8 N2 C16 116.3(2) . . ?
C6 C1 C2 120.3(2) . . ?
C6 C1 N1 119.3(2) . . ?
C2 C1 N1 120.3(2) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 C7 120.9(2) . . ?
C1 C2 C7 120.3(2) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 C7 C2 116.9(2) . . ?
N2 C7 S1 124.3(2) . . ?
C2 C7 S1 118.8(2) . . ?
C13 C8 C9 121.3(3) . . ?
C13 C8 N2 119.3(3) . . ?
C9 C8 N2 119.3(2) . . ?
C8 C9 C10 118.6(3) . . ?
C8 C9 C14 120.5(2) . . ?
C10 C9 C14 120.8(2) . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 119.3(3) . . ?
C8 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
N1 C14 C9 115.8(2) . . ?
N1 C14 S2 124.5(2) . . ?
C9 C14 S2 119.7(2) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
S1 C7 1.656(3) . ?
S2 C14 1.649(3) . ?
N1 C14 1.337(3) . ?
N1 C1 1.432(3) . ?
N1 C15 1.468(4) . ?
N2 C7 1.333(4) . ?
N2 C8 1.442(3) . ?
N2 C16 1.475(4) . ?
C1 C6 1.386(4) . ?
C1 C2 1.392(3) . ?
C2 C3 1.385(4) . ?
C2 C7 1.491(4) . ?
C3 C4 1.371(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C13 1.377(4) . ?
C8 C9 1.387(4) . ?
C9 C10 1.390(4) . ?
C9 C14 1.496(4) . ?
C10 C11 1.379(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C1T C6T 1.382(4) . ?
C1T C2T 1.402(4) . ?
C1T C7T 1.496(5) . ?
C2T C3T 1.394(4) . ?
C2T H2TA 0.9600 . ?
C3T C4T 1.385(4) . ?
C3T H3TA 0.9600 . ?
C4T C5T 1.399(4) . ?
C4T H4TA 0.9600 . ?
C5T C6T 1.395(4) . ?
C5T H5TA 0.9601 . ?
C6T H6TA 0.9601 . ?
C7T H7TA 0.9600 . ?
C7T H7TB 0.9601 . ?
C7T H7TC 0.9600 . ?
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
C14 N1 C1 C6 -112.5(3) . . . . ?
C15 N1 C1 C6 69.1(4) . . . . ?
C14 N1 C1 C2 71.1(3) . . . . ?
C15 N1 C1 C2 -107.2(3) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
N1 C1 C2 C3 176.0(2) . . . . ?
C6 C1 C2 C7 -175.3(2) . . . . ?
N1 C1 C2 C7 1.0(4) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C7 C2 C3 C4 175.6(3) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 C5 C6 C1 0.5(5) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
N1 C1 C6 C5 -176.7(3) . . . . ?
C8 N2 C7 C2 -3.4(4) . . . . ?
C16 N2 C7 C2 176.5(3) . . . . ?
C8 N2 C7 S1 177.8(2) . . . . ?
C16 N2 C7 S1 -2.3(4) . . . . ?
C3 C2 C7 N2 116.0(3) . . . . ?
C1 C2 C7 N2 -69.1(3) . . . . ?
C3 C2 C7 S1 -65.1(3) . . . . ?
C1 C2 C7 S1 109.8(3) . . . . ?
C7 N2 C8 C13 -110.5(3) . . . . ?
C16 N2 C8 C13 69.6(4) . . . . ?
C7 N2 C8 C9 72.7(4) . . . . ?
C16 N2 C8 C9 -107.3(3) . . . . ?
C13 C8 C9 C10 1.2(4) . . . . ?
N2 C8 C9 C10 178.0(2) . . . . ?
C13 C8 C9 C14 -174.9(3) . . . . ?
N2 C8 C9 C14 1.9(4) . . . . ?
C8 C9 C10 C11 -0.8(4) . . . . ?
C14 C9 C10 C11 175.3(3) . . . . ?
C9 C10 C11 C12 -0.3(5) . . . . ?
C10 C11 C12 C13 1.0(5) . . . . ?
C9 C8 C13 C12 -0.5(5) . . . . ?
N2 C8 C13 C12 -177.3(3) . . . . ?
C11 C12 C13 C8 -0.7(5) . . . . ?
C1 N1 C14 C9 -1.0(4) . . . . ?
C15 N1 C14 C9 177.3(3) . . . . ?
C1 N1 C14 S2 179.84(19) . . . . ?
C15 N1 C14 S2 -1.9(4) . . . . ?
C8 C9 C14 N1 -71.3(3) . . . . ?
C10 C9 C14 N1 112.7(3) . . . . ?
C8 C9 C14 S2 108.0(3) . . . . ?
C10 C9 C14 S2 -68.1(3) . . . . ?
