[1]Benzothiophene-Fused Chiral Spiro Polycyclic Aromatic Compounds: Optical Resolution, Functionalization, and Optical Properties.
Takase, Ko; Noguchi, Keiichi; Nakano, Koji; The Journal of organic chemistry 83 (2018) 15057–15065; doi:10.1021/acs.joc.8b02301

data_4034738
_publ_section_title
;
 [1]Benzothiophene-Fused Chiral Spiro Polycyclic Aromatic Compounds:
 Optical Resolution, Functionalization, and Optical Properties.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              15057
_journal_page_last               15065
_journal_paper_doi               10.1021/acs.joc.8b02301
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C31 H13 F6 O10 S4, C1 H1 Cl3'
_chemical_formula_sum            'C32 H15 Cl3 F6 O10 S4'
_chemical_formula_weight         908.03
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.41559(15)
_cell_length_b                   20.3317(4)
_cell_length_c                   21.2577(4)
_cell_measurement_reflns_used    25079
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      3.01
_cell_volume                     3637.26(12)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, 2004)'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34193
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         3.008
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    5.225
_exptl_absorpt_correction_T_max  0.593
_exptl_absorpt_correction_T_min  0.152
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 2544 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     496
_refine_ls_number_reflns         6584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0649P)^2^+1.5288P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                6278
_reflns_number_total             6584
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02301_si_002.cif
_cod_data_source_block           SO2SO2-OTf
_cod_original_cell_volume        3637.26(11)
_cod_database_code               4034738
_shelx_estimated_absorpt_t_min   0.161
_shelx_estimated_absorpt_t_max   0.623
_shelxl_version_number           2014-3
_shelx_res_checksum              91062
_shelx_hkl_checksum              64384