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_1554443
_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         'C30 H23 N O2'
_chemical_formula_sum            'C30 H23 N O2'
_chemical_formula_weight         429.49
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-10 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                109.541(6)
_cell_angle_beta                 103.435(7)
_cell_angle_gamma                90.850(6)
_cell_formula_units_Z            2
_cell_length_a                   7.3192(6)
_cell_length_b                   11.4476(7)
_cell_length_c                   14.2878(11)
_cell_measurement_reflns_used    4306
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.5580
_cell_measurement_theta_min      4.0480
_cell_volume                     1091.70(15)
_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_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.986
_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     23.00  88.00   1.00    0.15    --   48.20-113.00  74.00   65
  2  \w    -81.00 -33.00   1.00    0.15    --  -86.25 113.00 165.00   48
  3  \w   -104.00 -78.00   1.00    0.15    --  -86.25-113.00  74.00   26
  4  \w     79.00 111.00   1.00    0.15    --  107.75-113.00  74.00   32
  5  \w     48.00  78.00   1.00    0.15    --  107.75-113.00  74.00   30
  6  \w    100.00 136.00   1.00    0.15    --  107.75 113.00 165.00   36
  7  \w    -55.00  23.00   1.00    0.15    --  -48.20  37.00-120.00   78
  8  \w    -52.00  -9.00   1.00    0.15    --  -48.20 113.00 165.00   43
  9  \w    -86.00 -58.00   1.00    0.15    --  -48.20 113.00 165.00   28
 10  \w    -71.00  20.00   1.00    0.15    --  -48.20  77.00 -60.00   91
 11  \w   -120.00 -74.00   1.00    0.15    --  -48.20-125.00-120.00   46
 12  \w   -157.00-116.00   1.00    0.15    --  -86.25 -99.00-120.00   41
 13  \w   -162.00 -73.00   1.00    0.15    --  -86.25 -19.00 120.00   89
 14  \w   -108.00 -83.00   1.00    0.15    --  -86.25 -99.00-120.00   25
 15  \w     42.00 131.00   1.00    0.15    --  107.75 -77.00 150.00   89
 16  \w    129.00 174.00   1.00    0.15    --  107.75  37.00  60.00   45
 17  \w     97.00 123.00   1.00    0.15    --  107.75  37.00  60.00   26
 18  \w     70.00 106.00   1.00    0.15    --  107.75 -99.00 150.00   36
 19  \w     35.00  66.00   1.00    0.15    --  107.75 -99.00 150.00   31
 20  \w     35.00 108.00   1.00    0.15    --  107.75 -57.00  30.00   73
 21  \w     51.00 115.00   1.00    0.15    --  107.75-125.00  30.00   64
 22  \w     95.00 178.00   1.00    0.15    --  107.75  19.00   0.00   83
 23  \w     95.00 173.00   1.00    0.15    --  107.75  37.00  90.00   78
 24  \w     35.00 119.00   1.00    0.15    --  107.75 -57.00-150.00   84
;
_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      -0.0713291000
_diffrn_orient_matrix_UB_12      -0.1385434000
_diffrn_orient_matrix_UB_13      -0.0586681000
_diffrn_orient_matrix_UB_21      -0.0195534000
_diffrn_orient_matrix_UB_22      -0.0150953000
_diffrn_orient_matrix_UB_23      0.1005079000
_diffrn_orient_matrix_UB_31      -0.2045551000
_diffrn_orient_matrix_UB_32      0.0343446000
_diffrn_orient_matrix_UB_33      -0.0208086000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9483
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         4.119
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42106
_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_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0786P)^2^+0.2490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1468
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3100
_reflns_number_total             3840
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00887f2.cif
_cod_data_source_block           180524lxy-1
_cod_database_code               1554443
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 98.95
_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.a Ternary CH refined with riding coordinates:
 C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C3(H3), C6(H6), C8(H8), C25(H25), C22(H22), C19(H19), C16(H16),
 C5(H5), C4(H4), C23(H23), C17(H17), C18(H18), C24(H24)
2.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              45877
_shelx_hkl_checksum              48440
_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 2.679
_oxdiff_exptl_absorpt_empirical_full_min 0.505