Yb(OTf)3 catalyzed [3+2] annulations of D−A cyclopropanes with β-oxodithioesters：a regioselective synthesis of tetrahydrothiophenes
Wang, Shu-Wen; Guo, Wei-Si; Wen, Li-Rong; Li, Ming; RSC Adv.  (2015) –; doi:10.1039/C5RA06355H

data_7220536
_publ_section_title
;
 Yb(OTf)3 catalyzed [3+2] annulations of D&#x2212;A cyclopropanes with
 \b-oxodithioesters&#xFF1A;a regioselective synthesis of
 tetrahydrothiophenes
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA06355H
_journal_year                    2015
_chemical_formula_moiety         'C24 H23 Cl O5 S'
_chemical_formula_sum            'C24 H23 Cl O5 S'
_chemical_formula_weight         458.93
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-03-19
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2014-03-24 deposited with the CCDC.
2015-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                63.166(11)
_cell_angle_beta                 74.738(14)
_cell_angle_gamma                83.873(16)
_cell_formula_units_Z            2
_cell_length_a                   8.750(2)
_cell_length_b                   11.792(3)
_cell_length_c                   12.599(3)
_cell_measurement_reflns_used    3358
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4824
_cell_measurement_theta_min      1.8672
_cell_volume                     1119.0(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2013)'
_computing_structure_solution
;
'XS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0057
_diffrn_orient_matrix_UB_12      -0.0999
_diffrn_orient_matrix_UB_13      0.0635
_diffrn_orient_matrix_UB_21      -0.0933
_diffrn_orient_matrix_UB_22      -0.0068
_diffrn_orient_matrix_UB_23      -0.0166
_diffrn_orient_matrix_UB_31      0.0552
_diffrn_orient_matrix_UB_32      -0.0213
_diffrn_orient_matrix_UB_33      -0.0700
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9383
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.199
_diffrn_reflns_theta_min         1.867
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.036
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4014
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0975
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1115P)^2^+2.1461P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2423
_refine_ls_wR_factor_ref         0.2535
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3462
_reflns_number_total             4014
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra06355h2.cif
_cod_data_source_block           mx2895a
_cod_original_cell_volume        1118.9(5)
_cod_database_code               7220536
_shelxl_version_number           2013-4
_diffrn_number_total             5130
_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
2. Restrained distances
 C24-C23
 1.54 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C20(H20A,H20B), C23(H23A,H23B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C8(H8), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              23996
_shelx_hkl_checksum              99328