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_1554445
_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 Br Co P S'
_chemical_formula_sum            'C28 H29 Br Co P S'
_chemical_formula_weight         567.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2018-07-10 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6717(15)
_cell_length_b                   10.051(2)
_cell_length_c                   14.516(6)
_cell_measurement_reflns_used    2768
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      27.9070
_cell_measurement_theta_min      3.4460
_cell_volume                     2432.4(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -52.00  18.00   2.00   17.00    --    5.49 -37.00 120.00   35
  2  \w    -59.00 -13.00   2.00   17.00    --    5.49  -5.00 179.00   23
  3  \w    -23.00  23.00   2.00   17.00    --   -4.48 -99.00 -90.00   23
;
_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      -0.0262733000
_diffrn_orient_matrix_UB_12      0.0000778000
_diffrn_orient_matrix_UB_13      -0.0467277000
_diffrn_orient_matrix_UB_21      -0.0816009000
_diffrn_orient_matrix_UB_22      0.0029923000
_diffrn_orient_matrix_UB_23      -0.0142118000
_diffrn_orient_matrix_UB_31      0.0058147000
_diffrn_orient_matrix_UB_32      0.0424305000
_diffrn_orient_matrix_UB_33      0.0011078000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0790
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10560
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.335
_diffrn_reflns_theta_min         3.472
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.515
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.30c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.024(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3956
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+1.6460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1016
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3493
_reflns_number_total             3956
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00887f2.cif
_cod_data_source_block           171016lxy-3
_cod_database_code               1554445
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         CHCoBrSP
_diffrn_oxdiff_ac3_digest_frames
;
01f4208f8ffaa94594a707114c2ce9c60e00081cc9a
;
_diffrn_oxdiff_ac3_digest_hkl
;
0161f59dc072bf4d415c8d237fb2e4bef077f2
;
_reflns_odcompleteness_completeness 92.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H5(0.034) H10(0.027) H18A(0.057) H18B(0.057) H18C(0.057)
 H20(0.041) H22(0.033) H23(0.024) H24(0.036) H26(0.029) H31(0.03) H39(0.035)
 H40(0.039) H41(0.031) H43(0.03) H46(0.037) H47A(0.057) H47B(0.057) H47C(0.057)
 H51(0.038) H52A(0.062) H52B(0.062) H52C(0.062) H54A(0.063) H54B(0.063)
 H54C(0.063) H55A(0.056) H55B(0.056) H55C(0.056)
 Fixed X: H5(0.3805) H10(0.2674) H18A(0.3773) H18B(0.4323) H18C(0.3845)
 H20(0.4282) H22(0.1067) H23(0.0741) H24(-0.0338) H26(0.2484) H31(-0.0043) H39(-
 0.0133) H40(0.0417) H41(0.0351) H43(0.1338) H46(0.0186) H47A(0.1439)
 H47B(0.1835) H47C(0.1106) H51(0.3643) H52A(0.132) H52B(0.2124) H52C(0.1907)
 H54A(0.2924) H54B(0.3727) H54C(0.355) H55A(0.3011) H55B(0.3105) H55C(0.2253)
 Fixed Y: H5(0.8739) H10(0.7397) H18A(0.5207) H18B(0.4319) H18C(0.5508)
 H20(0.9435) H22(0.8726) H23(0.4941) H24(0.7891) H26(0.7601) H31(0.5669)
 H39(0.8688) H40(0.771) H41(0.8149) H43(0.6052) H46(0.9426) H47A(0.2917)
 H47B(0.1507) H47C(0.1884) H51(0.8827) H52A(0.0928) H52B(0.0125) H52C(0.0904)
 H54A(0.2066) H54B(0.1795) H54C(0.3216) H55A(0.5488) H55B(0.4178) H55C(0.4802)
 Fixed Z: H5(0.1453) H10(0.1376) H18A(0.2089) H18B(0.2712) H18C(0.3145)
 H20(0.285) H22(0.3403) H23(0.4199) H24(0.5558) H26(0.4121) H31(0.5388)
 H39(0.0638) H40(-0.0668) H41(0.208) H43(-0.0523) H46(0.4539) H47A(0.4719)
 H47B(0.4638) H47C(0.4006) H51(0.4176) H52A(0.2539) H52B(0.2598) H52C(0.1696)
 H54A(0.1002) H54B(0.1532) H54C(0.1135) H55A(0.4405) H55B(0.4981) H55C(0.4833)
;
_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 1.236
_oxdiff_exptl_absorpt_empirical_full_min 0.813