Organocatalyzed aerobic oxidative Robinson-type annulation of 2-isocyanochalcones: expedient synthesis of phenanthridines.
Hu, Zhongyan; Dong, Jinhuan; Men, Yang; Li, Yifei; Xu, Xianxiu; Chemical communications (Cambridge, England) 53 (2017) 1739–1742; doi:10.1039/c6cc09430a

data_7119516
_publ_section_title
;
 Organocatalyzed aerobic oxidative Robinson-type annulation of
 2-isocyanochalcones: expedient synthesis of phenanthridines.
;
_journal_issue                   10
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1739
_journal_page_last               1742
_journal_paper_doi               10.1039/c6cc09430a
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C19 H12 Cl N O'
_chemical_formula_sum            'C19 H12 Cl N O'
_chemical_formula_weight         305.75
_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_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-23 deposited with the CCDC.
2017-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.209(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4100(14)
_cell_length_b                   12.0649(15)
_cell_length_c                   11.7077(14)
_cell_measurement_reflns_used    2769
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.685
_cell_measurement_theta_min      2.969
_cell_volume                     1455.4(3)
_computing_cell_refinement       CrysAlis
_computing_data_collection       'CrysAlis (Oxford Diffraction,2006)'
_computing_data_reduction        CrysAlis
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12126
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.976
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1996'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.948
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.074(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0870
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1497P)^2^+3.1361P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2403
_refine_ls_wR_factor_ref         0.2767
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1860
_reflns_number_total             2550
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc09430a2.cif
_cod_data_source_block           4
_cod_depositor_comments          'Adding full bibliography for 7119516.cif.'
_cod_database_code               7119516
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              45101