Metal-Free Oxidative [2+2+1] Heteroannulation of 1,7-Enynes with Thiocyanates toward Thieno[3,4-c]quinolin-4(5H)-ones
Yu, Jiang-Xi; Niu, Shijie; Hu, Ming; Xiang, Jiannan; Li, Jin-Heng; Chemical Communications  (2019) –; doi:10.1039/C9CC02242B

data_7123422
_publ_section_title
;
 Metal-Free Oxidative [2+2+1] Heteroannulation of 1,7-Enynes with
 Thiocyanates toward Thieno[3,4-c]quinolin-4(5H)-ones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC02242B
_journal_year                    2019
_chemical_formula_moiety         'C20 H19 N O S'
_chemical_formula_sum            'C20 H19 N O S'
_chemical_formula_weight         321.42
_chemical_melting_point          436
_chemical_name_systematic
3a,5,8-trimethyl-1-phenyl-3,3a-dihydrothieno[3,4-c]quinolin-4(5H)-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc21x8nx
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-03-19 deposited with the CCDC.    2019-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.103(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2921(15)
_cell_length_b                   13.3688(17)
_cell_length_c                   10.0405(12)
_cell_measurement_reflns_used    2525
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.61
_cell_measurement_theta_min      2.57
_cell_volume                     1619.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9188
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.572
_diffrn_reflns_theta_min         1.688
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       lump
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.170
_exptl_transmission_factor_max   0.966
_exptl_transmission_factor_min   0.958
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3367
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0507P)^2^+0.4365P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1183
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2525
_reflns_number_total             3367
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc02242b2.cif
_cod_data_source_block           yjx204
_cod_database_code               7123422
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.966
_shelx_res_checksum              95751