Enantioselective Construction of Polyfunctionalized Spiroannulated Dihydrothiophenes via a Formal Thio [3+2] Cyclization.
Zeng, Xue-Mei; Meng, Chang-Yu; Bao, Jia-Xin; Xu, Dong-Cheng; Xie, Jian-Wu; Zhu, Wei-Dong; The Journal of organic chemistry 80 (2015) 11521–11528; doi:10.1021/acs.joc.5b01357

data_4031725
_publ_section_title
;
 Enantioselective Construction of Polyfunctionalized Spiroannulated
 Dihydrothiophenes via a Formal Thio [3+2] Cyclization.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11521
_journal_page_last               11528
_journal_paper_doi               10.1021/acs.joc.5b01357
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H21 Cl N2 O2 S'
_chemical_formula_sum            'C26 H21 Cl N2 O2 S'
_chemical_formula_weight         460.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-14
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.102(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0744(3)
_cell_length_b                   10.4491(3)
_cell_length_c                   21.6791(6)
_cell_measurement_reflns_used    9769
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.086
_cell_measurement_theta_min      2.160
_cell_volume                     2273.08(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            83234
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         0.943
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 3949 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.007(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         10421
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0398P)^2^+0.5550P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                9263
_reflns_number_total             10421
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01357_si_002.cif
_cod_data_source_block           150407_0m
_cod_depositor_comments          'Adding full bibliography for 4031725.cif.'
_cod_database_code               4031725
_shelxl_version_number           2013-2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C24(H24A,H24B), C29(H29A,H29B), C40(H40A,H40B)
2.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C32(H32), C37(H37), C44(H44), C46(H46), C47(H47), C49(H49),
 C52(H52), C54(H54), C55(H55), C59(H59), C60(H60), C26(H26), C35(H35), C38(H38),
  C41(H41), C42(H42), C43(H43), C45(H45), C48(H48), C51(H51), C53(H53),
 C56(H56), C57(H57)
2.d Idealised Me refined as rotating group:
 C58(H58A,H58B,H58C), C2(H2A,H2B,H2C)
2.e Idealised tetrahedral OH refined as rotating group:
 O9(H9), O11(H11)
;
_olex2_submission_special_instructions 'No special instructions were received'