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_1554442
_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         'C22 H18 N O2'
_chemical_formula_sum            'C22 H18 N O2'
_chemical_formula_weight         328.37
_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     dual
_audit_creation_date             2018-07-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-10 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.067(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7660(3)
_cell_length_b                   7.3952(2)
_cell_length_c                   18.2702(4)
_cell_measurement_reflns_used    5794
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.7990
_cell_measurement_theta_min      3.8010
_cell_volume                     1680.17(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -76.00 -46.00   1.00    0.10    --  -48.45  95.00 155.00   30
  2  \w      5.00  78.00   1.00    0.10    --   48.45 -95.00  46.00   73
  3  \w    -72.00 -46.00   1.00    0.40    --  -86.25  95.00 155.00   26
  4  \w   -157.00-131.00   1.00    0.40    --  -86.25 -95.00  46.00   26
  5  \w    102.00 152.00   1.00    0.40    --  107.75  95.00 155.00   50
  6  \w     58.00 108.00   1.00    0.40    --  107.75 -95.00  46.00   50
  7  \w   -120.00 -72.00   1.00    0.10    --  -48.45-125.00-150.00   48
  8  \w   -115.00 -75.00   1.00    0.10    --  -48.45-125.00  60.00   40
  9  \w    -61.00  15.00   1.00    0.10    --  -48.45  37.00 -90.00   76
 10  \w   -158.00 -83.00   1.00    0.40    --  -86.25 -99.00 120.00   75
 11  \w     94.00 175.00   1.00    0.40    --  107.75 125.00  90.00   81
 12  \w     37.00 120.00   1.00    0.40    --  107.75 -37.00  60.00   83
 13  \w     94.00 164.00   1.00    0.40    --  107.75 125.00-180.00   70
 14  \w     35.00 117.00   1.00    0.40    --  107.75-125.00-120.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0979227000
_diffrn_orient_matrix_UB_12      0.0374305000
_diffrn_orient_matrix_UB_13      -0.0339010000
_diffrn_orient_matrix_UB_21      -0.0102213000
_diffrn_orient_matrix_UB_22      -0.1906807000
_diffrn_orient_matrix_UB_23      -0.0348009000
_diffrn_orient_matrix_UB_31      -0.0752092000
_diffrn_orient_matrix_UB_32      0.0753015000
_diffrn_orient_matrix_UB_33      -0.0715875000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8706
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.067
_diffrn_reflns_theta_max         67.067
_diffrn_reflns_theta_min         3.849
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'fluorescent light colourless'
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             692
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2978
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.739
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0707
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0983P)^2^+1.0810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1844
_refine_ls_wR_factor_ref         0.1974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2596
_reflns_number_total             2978
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00887f2.cif
_cod_data_source_block           180629lxy-1
_cod_original_cell_volume        1680.16(7)
_cod_database_code               1554442
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CNO
_reflns_odcompleteness_completeness 98.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H19-H17
 2.45 with sigma of 0.02
 H17-H19
 2.45 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C22: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.08
C22 \\sim O21 \\sim C20 \\sim O23: within 1.7A with sigma of 0.004 and sigma
for terminal atoms of 0.008
4. Others
 Fixed Sof: H22(0.5) H22A(0.5) C2AA(0.5) H2AA(0.5) H2AB(0.5) H2AC(0.5)
 C1AA(0.5) H1AA(0.5) H1AB(0.5) H1AC(0.5)
5.a Ternary CH refined with riding coordinates:
 C19(H19)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C17(H17), C12(H12), C16(H16), C15(H15), C2(H2), C5(H5),
 C3(H3), C4(H4), C22(H22), C22(H22A)
5.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C2AA(H2AA,H2AB,H2AC), C1AA(H1AA,H1AB,H1AC)
;
_shelx_res_checksum              97053
_shelx_hkl_checksum              96289
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.114
_oxdiff_exptl_absorpt_empirical_full_min 0.462