N-Heterocyclic Carbene-Catalyzed Atom-Economical and Enantioselective Construction of the C–S Bond: Asymmetric Synthesis of Functionalized Thiochromans
Lu, Hong; Zhang, Jia-Lu; Liu, Jin-Yu; Li, Hong-Yu; Xu, Peng-Fei; ACS Catalysis 7 (2017) 7797–; doi:10.1021/acscatal.7b02651

data_4514246
_publ_section_title
;
 N-Heterocyclic Carbene-Catalyzed Atom-Economical and Enantioselective
 Construction of the C--S Bond: Asymmetric Synthesis of Functionalized
 Thiochromans
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              7797
_journal_paper_doi               10.1021/acscatal.7b02651
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H18 O2 S'
_chemical_formula_sum            'C24 H18 O2 S'
_chemical_formula_weight         370.44
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-03-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5092(6)
_cell_length_b                   12.3167(8)
_cell_length_c                   15.9826(8)
_cell_measurement_reflns_used    1366
_cell_measurement_temperature    290.56(10)
_cell_measurement_theta_max      25.6920
_cell_measurement_theta_min      3.9410
_cell_volume                     1871.91(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      290.56(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega   18.00   59.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000  -90.0000 41

  2 omega  -52.00   55.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  120.0000 107
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0494623000
_diffrn_orient_matrix_UB_12      0.0420727000
_diffrn_orient_matrix_UB_13      -0.0071988000
_diffrn_orient_matrix_UB_21      -0.0553026000
_diffrn_orient_matrix_UB_22      0.0386298000
_diffrn_orient_matrix_UB_23      -0.0004596000
_diffrn_orient_matrix_UB_31      0.0075590000
_diffrn_orient_matrix_UB_32      0.0073161000
_diffrn_orient_matrix_UB_33      0.0438003000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4706
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.55
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(10)
_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     244
_refine_ls_number_reflns         3396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0418P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1064
_reflns_number_gt                2843
_reflns_number_total             3396
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs7b02651_si_002.cif
_cod_data_source_block           luh_0328
_cod_depositor_comments          'Adding full bibliography for 4514246.cif.'
_cod_database_code               4514246
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 99.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_olex2_date_sample_data_collection 2017-03-28
_olex2_submission_special_instructions 'No special instructions were received'