Synthesis of Functionalized Phenanthrenes via Regioselective Oxidative Radical Cyclization.
Pati, Kamalkishore; Michas, Christopher; Allenger, David; Piskun, Ilya; Coutros, Peter S.; Gomes, Gabriel Dos Passos; Alabugin, Igor V.; The Journal of organic chemistry 80 (2015) 11706–11717; doi:10.1021/acs.joc.5b01014

data_4031345
_publ_section_title
;
 Synthesis of Functionalized Phenanthrenes via Regioselective Oxidative
 Radical Cyclization.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11706
_journal_page_last               11717
_journal_paper_doi               10.1021/acs.joc.5b01014
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C20 H0 I'
_chemical_formula_weight         367.10
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                64.8970(10)
_cell_angle_beta                 77.0440(10)
_cell_angle_gamma                70.1210(10)
_cell_formula_units_Z            2
_cell_length_a                   8.6796(8)
_cell_length_b                   9.6049(9)
_cell_length_c                   10.2306(9)
_cell_measurement_temperature    173(2)
_cell_volume                     723.10(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.930
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15332
_diffrn_reflns_theta_full        35.18
_diffrn_reflns_theta_max         35.18
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    2.202
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             346
_refine_diff_density_max         1.055
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         5990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0192
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0272P)^2^+0.2982P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0499
_refine_ls_wR_factor_ref         0.0504
_reflns_number_gt                5795
_reflns_number_total             5990
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01014_si_002.cif
_cod_data_source_block           c:\users\hoatam~1\desktop\ks10_1~1\p11
_cod_depositor_comments          'Adding full bibliography for 4031345.cif.'
_cod_database_code               4031345