Yb(OTf)3-Mediated Access to Furans from β-Ketothioamides via Eschenmoser Sulfide Contraction Reaction.
Li, Ming; Kong, Xiang-Jing; Wen, Li-Rong; The Journal of organic chemistry 80 (2015) 11999–12005; doi:10.1021/acs.joc.5b01924

data_4036426
_publ_section_title
;
 Yb(OTf)3-Mediated Access to Furans from \b-Ketothioamides via Eschenmoser
 Sulfide Contraction Reaction.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11999
_journal_page_last               12005
_journal_paper_doi               10.1021/acs.joc.5b01924
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C23 H17 N O2'
_chemical_formula_sum            'C23 H17 N O2'
_chemical_formula_weight         339.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-06-17
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.188(4)
_cell_length_b                   21.229(8)
_cell_length_c                   7.164(3)
_cell_measurement_reflns_used    5083
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4787
_cell_measurement_theta_min      1.8202
_cell_volume                     1701.5(11)
_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  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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      0.0097
_diffrn_orient_matrix_UB_12      0.1246
_diffrn_orient_matrix_UB_13      -0.0621
_diffrn_orient_matrix_UB_21      -0.0743
_diffrn_orient_matrix_UB_22      -0.0174
_diffrn_orient_matrix_UB_23      -0.0465
_diffrn_orient_matrix_UB_31      -0.0260
_diffrn_orient_matrix_UB_32      0.0191
_diffrn_orient_matrix_UB_33      0.0343
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6740
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         0.959
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       rod
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 765 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   1.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3579
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0857
_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^)+(0.0034P)^2^+1.9444P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1420
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    0.851
_reflns_Friedel_fraction_max     0.821
_reflns_number_gt                2744
_reflns_number_total             3579
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01924_si_001.cif
_cod_data_source_block           a
_cod_database_code               4036426
_shelxl_version_number           2013-4
_diffrn_number_total             2273
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_shelx_res_checksum              19131
_shelx_hkl_checksum              2763