Radical cyclization of benzene-tethered 1,7-enynes with aryldiazonium tetrafluoroborates: a facile route to benzo[j]phenanthridines
An, Yuanyuan; Zhang, Jun; Xia, Hongguang; Wu, Jie; Organic Chemistry Frontiers 4 (2017) 1318–; doi:10.1039/C7QO00193B

data_1553767
_publ_section_title
;
 Radical cyclization of benzene-tethered 1,7-enynes with aryldiazonium
 tetrafluoroborates: a facile route to benzo[j]phenanthridines
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1318
_journal_paper_doi               10.1039/C7QO00193B
_journal_volume                  4
_journal_year                    2017
_chemical_formula_sum            'C26 H20 F3 N O'
_chemical_formula_weight         419.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-01-17 deposited with the CCDC.
2017-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                98.780(4)
_cell_angle_beta                 90.325(4)
_cell_angle_gamma                108.111(4)
_cell_formula_units_Z            2
_cell_length_a                   9.3089(19)
_cell_length_b                   10.692(2)
_cell_length_c                   10.826(2)
_cell_measurement_reflns_used    1255
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.55
_cell_measurement_theta_min      2.31
_cell_volume                     1010.5(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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0292
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6671
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         1.906
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1628P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1912
_refine_ls_wR_factor_ref         0.2556
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2252
_reflns_number_total             3930
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00193b2.cif
_cod_data_source_block           mo_60926b
_cod_original_cell_volume        1010.6(4)
_cod_database_code               1553767
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              41884
_shelx_hkl_checksum              76331