N-Heterocyclic carbene-catalyzed diastereoselective synthesis of sulfenylated indanes via sulfa-Michael-Michael (aldol) cascade reactions.
Feng, Ze-Nan; Luo, Jin-Yun; Zhang, Yang; Du, Guang-Fen; He, Lin; Organic & biomolecular chemistry 17 (2019) 4700–4704; doi:10.1039/c9ob00210c

data_7156810
_publ_section_title
;
 N-Heterocyclic carbene-catalyzed diastereoselective synthesis of
 sulfenylated indanes via sulfa-Michael-Michael (aldol) cascade reactions.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4700
_journal_page_last               4704
_journal_paper_doi               10.1039/c9ob00210c
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C30 H24 O2 S'
_chemical_formula_sum            'C30 H24 O2 S'
_chemical_formula_weight         448.55
_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             2019-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_audit_update_record
;
2019-03-26 deposited with the CCDC.    2019-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   7.6174(3)
_cell_length_b                   26.7210(13)
_cell_length_c                   34.0314(14)
_cell_measurement_temperature    293(2)
_cell_volume                     6926.9(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1019
_diffrn_reflns_av_unetI/netI     0.1321
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            37759
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.36
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.9708
_exptl_absorpt_correction_T_min  0.9676
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.39(8)
_refine_ls_extinction_coef       0.00115(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     894
_refine_ls_number_reflns         13802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1403
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0330P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1306
_reflns_number_gt                7935
_reflns_number_total             13802
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob00210c2.cif
_cod_data_source_block           p1
_cod_depositor_comments          'Adding full bibliography for 7156810.cif.'
_cod_database_code               7156810
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.61(8) 0.39(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C15(H15), C37(H37), C44(H44), C45(H45), C67(H67), C74(H74),
 C75(H75)
3.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C53(H53A,H53B), C83(H83A,H83B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C26(H26), C27(H27), C28(H28),
  C29(H29), C30(H30), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36),
 C39(H39), C40(H40), C41(H41), C42(H42), C48(H48), C49(H49), C50(H50), C51(H51),
  C52(H52), C56(H56), C57(H57), C58(H58), C59(H59), C60(H60), C62(H62),
 C63(H63), C64(H64), C65(H65), C66(H66), C69(H69), C70(H70), C71(H71), C72(H72),
  C78(H78), C79(H79), C80(H80), C81(H81), C82(H82), C86(H86), C87(H87),
 C88(H88), C89(H89), C90(H90)
;
_olex2_submission_special_instructions 'No special instructions were received'