Rhodium-catalyzed reactions of dithiols and 1,4-bis(bromomethyl)benzenes leading to enantioenriched dithiaparacyclophanes.
Tanaka, Ken; Hori, Tomoko; Osaka, Takuya; Noguchi, Keiichi; Hirano, Masao; Organic letters 9 (2007) 4881–4884; doi:10.1021/ol702242x

data_1505617
_publ_section_title
;
 Rhodium-catalyzed reactions of dithiols and 1,4-bis(bromomethyl)benzenes
 leading to enantioenriched dithiaparacyclophanes.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              4881
_journal_page_last               4884
_journal_paper_doi               10.1021/ol702242x
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H14 Br2 S2'
_chemical_formula_sum            'C16 H14 Br2 S2'
_chemical_formula_weight         430.21
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                91.288(1)
_cell_angle_beta                 105.065(1)
_cell_angle_gamma                103.457(1)
_cell_formula_units_Z            2
_cell_length_a                   6.8118(1)
_cell_length_b                   9.8890(2)
_cell_length_c                   12.2513(2)
_cell_measurement_reflns_used    13988
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.8
_cell_volume                     772.00(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_sigmaI/netI    0.0882
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14150
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         3.75
_exptl_absorpt_coefficient_mu    9.067
_exptl_absorpt_correction_T_max  0.762
_exptl_absorpt_correction_T_min  0.086
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.586
_refine_diff_density_min         -1.172
_refine_diff_density_rms         0.137
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881 2253 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5020
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0434
_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/[\s^2^(Fo^2^)+(0.0337P)^2^+0.2710P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1000
_reflns_number_gt                4854
_reflns_number_total             5020
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol702242x-file001.cif
_cod_data_source_block           I
_cod_original_cell_volume        771.99(2)
_cod_database_code               1505617