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_4023508
_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         'C16 H14 N2 S2, 2(c6 H F5 O)'
_chemical_formula_sum            'C28 H16 F10 N2 O2 S2'
_chemical_formula_weight         666.55
_chemical_name_systematic
; 
5,11-dimethyldibenzo[b,f][1,5]diazocine-6,12(5H,11H)-dithione
bis-pentafluorophenol co-crystal
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.493(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.417(3)
_cell_length_b                   7.5864(8)
_cell_length_c                   17.247(2)
_cell_measurement_reflns_used    4537
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     2789.5(6)
_computing_cell_refinement
;
CrysAlis CCD
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2007)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2007)
;
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Kuma KM4CCD \k geometry'
_diffrn_measurement_method       '\w 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  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5998
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         4.18
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0028(7)
_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   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0442
_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/[\s^2^(Fo^2^)+(0.0853P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1413
_reflns_number_gt                1685
_reflns_number_total             2449
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo8004809-File005.cif
_cod_data_source_block           (+-)-2b-C6F5OH
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4023508