Enantiomeric Resolution of N,N'-Dimethyldithiodianthranilide through Diastereomeric Silver(I) Complex. Circular Dichroism Spectra, Racemization Barrier, and Molecular Self-Assembly
Teresa Olszewska; Maria Gdaniec; Tadeusz Połoński; Journal of Organic Chemistry 73 (2008) 4859–4864; doi:10.1021/jo8004809

data_4023509
_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       '\w/2\q 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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0761P)^2^+0.4729P] where P=(Fo^2^+2Fc^2^)/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>2\s(I)
_cod_data_source_file            jo8004809-File006.cif
_cod_data_source_block           (+-)-2b-toluene
_cod_database_code               4023509