Enantiomerically Pure [2.2]Paracyclophane-4-thiol: A Planar Chiral Sulfur-Based Building Block Readily Available by Resolution with an Amino Acid Chiral Auxiliary.
Vincent, Adrien; Deschamps, Damien; Martzel, Thomas; Lohier, Jean-François; Richards, Christopher J.; Gaumont, Annie-Claude; Perrio, Stéphane; The Journal of organic chemistry 81 (2016) 3961–3966; doi:10.1021/acs.joc.6b00560

data_4036796
_publ_section_title
;
 Enantiomerically Pure [2.2]Paracyclophane-4-thiol: A Planar Chiral
 Sulfur-Based Building Block Readily Available by Resolution with an Amino
 Acid Chiral Auxiliary.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3961
_journal_page_last               3966
_journal_paper_doi               10.1021/acs.joc.6b00560
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H16 S'
_chemical_formula_sum            'C16 H16 S'
_chemical_formula_weight         240.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.653(2)
_cell_length_b                   10.942(3)
_cell_length_c                   15.068(6)
_cell_measurement_reflns_used    8942
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.08
_cell_measurement_theta_min      2.30
_cell_volume                     1261.8(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1119
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20315
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.308
_diffrn_reflns_theta_min         2.300
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1000 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         3124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0582
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0953P)^2^+0.0545P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1558
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2713
_reflns_number_total             3124
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00560_si_001.cif
_cod_data_source_block           deschamps18_0m
_cod_original_cell_volume        1261.6(7)
_cod_database_code               4036796
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              67217
_shelx_hkl_checksum              21312