NaH promoted [4+3] annulation of crotonate-derived sulfur ylides and thioaurones: synthesis of 2,5-dihydrobenzo[4,5] thieno[3,2-b]oxepine
Zhang, Youquan; Yu, aimin; jia, jiru; Ma, Shanshan; Li, Ke; Wei, Yin; Meng, Xiangtai; Chem. Commun.  (2017) –; doi:10.1039/C7CC04466F

data_7120616
_publ_section_title
;
 NaH promoted [4+3] annulation of crotonate-derived sulfur ylides and
 thioaurones: synthesis of 2,5-dihydrobenzo[4,5] thieno[3,2-b]oxepine
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC04466F
_journal_year                    2017
_chemical_formula_sum            'C20 H15 Cl O4 S'
_chemical_formula_weight         386.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-05-11 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 130.740(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.3420(19)
_cell_length_b                   8.9941(7)
_cell_length_c                   20.0725(13)
_cell_measurement_reflns_used    3989
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      66.42
_cell_measurement_theta_min      4.43
_cell_volume                     3603.2(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9837
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        66.767
_diffrn_reflns_theta_max         66.767
_diffrn_reflns_theta_min         4.430
_exptl_absorpt_coefficient_mu    3.160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       Block
_exptl_crystal_F_000             1600
_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         0.376
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0678P)^2^+2.8604P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1212
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2512
_reflns_number_total             3123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc04466f2.cif
_cod_data_source_block           1_a
_cod_original_cell_volume        3603.2(5)
_cod_database_code               7120616
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.543
_shelx_estimated_absorpt_t_max   0.600
_shelx_res_checksum              56631