Copper-Catalyzed One-Pot Cross-Dehydrogenative Thienannulation: Chemoselective Access to Naphtho[2,1-b]thiophene-4,5-diones and Subsequent Transformation to Benzo[a]thieno[3,2-c]phenazines.
Shukla, Gaurav; Srivastava, Abhijeet; Yadav, Dhananjay; Singh, Maya Shankar; The Journal of organic chemistry 83 (2018) 2173–2181; doi:10.1021/acs.joc.7b03092

data_4033449
_publ_section_title
;
 Copper-Catalyzed One-Pot Cross-Dehydrogenative Thienannulation:
 Chemoselective Access to Naphtho[2,1-b]thiophene-4,5-diones and
 Subsequent Transformation to Benzo[a]thieno[3,2-c]phenazines.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2173
_journal_page_last               2181
_journal_paper_doi               10.1021/acs.joc.7b03092
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C20 H14 O4 S2'
_chemical_formula_sum            'C20 H14 O4 S2'
_chemical_formula_weight         382.43
_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_method           SHELXL-2016/6
_cell_angle_alpha                94.382(5)
_cell_angle_beta                 96.169(5)
_cell_angle_gamma                111.538(5)
_cell_formula_units_Z            2
_cell_length_a                   8.198(5)
_cell_length_b                   8.834(5)
_cell_length_c                   12.549(5)
_cell_measurement_reflns_used    3092
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.498
_cell_measurement_theta_min      2.498
_cell_volume                     833.8(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX'
_computing_data_reduction        'Bruker SAINT PLUS'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SIR97(Altomare, et. al. 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10527
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.498
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0415P)^2^+0.5132P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2667
_reflns_number_total             3092
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03092_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 4033449.cif.'
_cod_database_code               4033449
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.814
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              62675
_shelx_hkl_checksum              66620