Substrate-Controlled Domino Reactions of Crotonate-Derived Sulfur Ylides: Synthesis of Benzothiophene Derivatives.
Ding, Wenhuan; Zhang, Youquan; Yu, Aimin; Zhang, Lei; Meng, Xiangtai; The Journal of organic chemistry 83 (2018) 13821–13833; doi:10.1021/acs.joc.8b02152

data_4034848
_publ_section_title
;
 Substrate-Controlled Domino Reactions of Crotonate-Derived Sulfur Ylides:
 Synthesis of Benzothiophene Derivatives.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13821
_journal_page_last               13833
_journal_paper_doi               10.1021/acs.joc.8b02152
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C3.5 H3 Cl0.33 O0.5 S0.33'
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_space_group_crystal_system      triclinic
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_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                105.417(4)
_cell_angle_beta                 90.289(4)
_cell_angle_gamma                98.775(4)
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_cell_length_a                   9.7362(8)
_cell_length_b                   14.1432(11)
_cell_length_c                   15.9734(12)
_cell_measurement_reflns_used    8188
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      62.47
_cell_measurement_theta_min      2.87
_cell_volume                     2093.2(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_av_unetI/netI     0.0899
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20920
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        63.209
_diffrn_reflns_theta_max         63.209
_diffrn_reflns_theta_min         2.873
_exptl_absorpt_coefficient_mu    4.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         1.681
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         6611
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1533
_refine_ls_R_factor_gt           0.1086
_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^)+(0.1937P)^2^+5.3042P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2805
_refine_ls_wR_factor_ref         0.3136
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4437
_reflns_number_total             6611
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02152_si_005.cif
_cod_data_source_block           33
_cod_original_formula_sum        'C3.50 H3 Cl0.33 O0.50 S0.33'
_cod_database_code               4034848
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.417
_shelx_estimated_absorpt_t_max   0.477
_shelx_res_checksum              55648
_shelx_hkl_checksum              21312