Synthesis of Polycyclic Heteroaromatic Coumarins via Photoinduced Dehydrogenative Annulation of 4-Phenyl-3-heteroarylcoumarins.
Shi, Juan; Kang, Yang; Wang, Tao; Liang, Yong; Zhang, Zunting; The Journal of organic chemistry 83 (2018) 13940–13948; doi:10.1021/acs.joc.8b02290

data_4034894
_publ_section_title
;
 Synthesis of Polycyclic Heteroaromatic Coumarins via Photoinduced
 Dehydrogenative Annulation of 4-Phenyl-3-heteroarylcoumarins.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13940
_journal_page_last               13948
_journal_paper_doi               10.1021/acs.joc.8b02290
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C20 H12 O2 S'
_chemical_formula_weight         316.36
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.9342(17)
_cell_length_b                   16.527(4)
_cell_length_c                   21.431(5)
_cell_measurement_reflns_used    9750
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      5.353
_cell_measurement_theta_min      68.250
_cell_volume                     2810.2(11)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35147
_diffrn_reflns_theta_full        68.61
_diffrn_reflns_theta_max         68.61
_diffrn_reflns_theta_min         5.35
_exptl_absorpt_coefficient_mu    2.102
_exptl_absorpt_correction_T_max  0.5712
_exptl_absorpt_correction_T_min  0.4196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(sadabs; Bruker, 1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0662P)^2^+1.2657P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                2342
_reflns_number_total             2518
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b02290_si_003.cif
_cod_data_source_block           s
_cod_original_cell_volume        2810.2(10)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4034894