Organocatalytic Enantioselective Construction of Axially Chiral Sulfone-Containing Styrenes.
Jia, Shiqi; Chen, Zhili; Zhang, Nan; Tan, Yu; Liu, Yidong; Deng, Jun; Yan, Hailong; Journal of the American Chemical Society 140 (2018) 7056–7060; doi:10.1021/jacs.8b03211

data_4132366
_publ_section_title
;
 Organocatalytic Enantioselective Construction of Axially Chiral
 Sulfone-Containing Styrenes.
;
_journal_issue                   23
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7056
_journal_page_last               7060
_journal_paper_doi               10.1021/jacs.8b03211
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H18 O3 S'
_chemical_formula_sum            'C24 H18 O3 S'
_chemical_formula_weight         386.44
_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     dual
_audit_creation_date             2017-12-06
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.06.06 svn.r3414 for OlexSys, GUI svn.r5353)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0521(4)
_cell_length_b                   12.6929(8)
_cell_length_c                   15.0985(8)
_cell_measurement_reflns_used    2537
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      25.7510
_cell_measurement_theta_min      4.0260
_cell_volume                     1926.42(18)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      292(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7484
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_min         3.375
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       Block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1201 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0330P)^2^+0.3168P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3317
_reflns_number_total             3922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b03211_si_002.cif
_cod_data_source_block           20171130-yanhl-jsq-2
_cod_database_code               4132366
_shelx_shelxl_version_number     2014/7
_oxdiff_exptl_absorpt_empirical_full_min 0.846
_oxdiff_exptl_absorpt_empirical_full_max 1.196
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C7(H7), C17(H17), C14(H14), C12(H12), C15(H15), C16(H16), C20(H20),
 C1(H1A), C5(H5), C3(H3), C4(H4), C21(H21), C2(H2), C24(H24), C22(H22), C23(H23)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'