Cobalt-catalyzed radical cyclization of isocyanides forming phenanthridine derivatives
Liu, Xiangyu; Wu, Chengjuan; Zhang, Jing; Shi, Yihan; Zhang, Shengnan; Geng, Yan; Tung, Chen-Ho; Wang, Wenguang; Organic Chemistry Frontiers 5 (2018) 2997–; doi:10.1039/C8QO00887F

data_1554441
_publ_section_title
;
 Cobalt-catalyzed radical cyclization of isocyanides forming
 phenanthridine derivatives
;
_journal_issue                   20
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2997
_journal_paper_doi               10.1039/C8QO00887F
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C28 H29 Co P S'
_chemical_formula_sum            'C28 H29 Co P S'
_chemical_formula_weight         487.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-07-09
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-07-10 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.640(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0319(4)
_cell_length_b                   18.9034(9)
_cell_length_c                   14.4632(7)
_cell_measurement_reflns_used    9766
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.439
_cell_measurement_theta_min      2.534
_cell_volume                     2452.8(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart APEX II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16180
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.779
_exptl_absorpt_coefficient_mu    0.863
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0622 before and 0.0329 after correction.
The Ratio of minimum to maximum transmission is 0.8581.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             1020
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0285
_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^)+(0.0356P)^2^+1.4594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0740
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3782
_reflns_number_total             4327
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00887f2.cif
_cod_data_source_block           p
_cod_database_code               1554441
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C24(H24), C25(H25), C31(H31), C34(H34), C40(H40), C51(H51),
 C63(H63), C72(H72), C78(H78), C91(H91), C97(H97), C103(H103), C0AA(H0AA)
2.b Idealised Me refined as rotating group:
 C56(H56A,H56B,H56C), C82(H82A,H82B,H82C), C84(H84A,H84B,H84C), C85(H85A,H85B,
 H85C), C5(H5A,H5B,H5C)
;
_olex2_submission_special_instructions 'No special instructions were received'