Ru-Catalyzed One-Pot Diannulation of Heteroaryls: Direct Access to π-Conjugated Polycyclic Amides.
Shankar, Majji; Ghosh, Koushik; Mukherjee, Kallol; Rit, Raja K.; Sahoo, Akhila K.; Organic letters 18 (2016) 6416–6419; doi:10.1021/acs.orglett.6b03314

data_1555972
_publ_section_title
;
 Ru-Catalyzed One-Pot Diannulation of Heteroaryls: Direct Access to
 \p-Conjugated Polycyclic Amides.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6416
_journal_page_last               6419
_journal_paper_doi               10.1021/acs.orglett.6b03314
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C35 H22 F N O'
_chemical_formula_weight         491.54
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 107.487(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.6372(12)
_cell_length_b                   11.5066(9)
_cell_length_c                   12.8191(9)
_cell_measurement_reflns_used    6492
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.42
_cell_volume                     2481.3(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1178
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35350
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         2.421
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0614P)^2^+0.3516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1335
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2968
_reflns_number_total             4375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03314_si_004.cif
_cod_data_source_block           aks19vr_a_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C35 H22 F1 N1 O1'
_cod_database_code               1555972
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              17128
_shelx_hkl_checksum              90354