Cobalt(II)-Catalyzed Bis-isocyanides Insertion Reactions with Sulfonyl Azides via Nitrene Radical: Chemoselective Synthesis of The Sulfonylamidyl amide and 3-Imine Indole Derivatives
Gu, Zheng-Yang; Li, Jing-Hao; Wang, Shun-Yi; Ji, Shun-Jun; Chem. Commun.  (2017) –; doi:10.1039/C7CC06531K

data_7120677
_publ_section_title
;
 Cobalt(II)-Catalyzed Bis-isocyanides Insertion Reactions with Sulfonyl
 Azides via Nitrene Radical: Chemoselective Synthesis of The
 Sulfonylamidyl amide and 3-Imine Indole Derivatives
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC06531K
_journal_year                    2017
_chemical_formula_moiety         'C17 H27 N3 O3 S'
_chemical_formula_sum            'C17 H27 N3 O3 S'
_chemical_formula_weight         353.47
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_audit_creation_date             2017-06-02
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
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_audit_update_record
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2017-07-21 deposited with the CCDC.
2017-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.006(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.6550(6)
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_cell_length_c                   29.9934(14)
_cell_measurement_reflns_used    2802
_cell_measurement_temperature    284.94(10)
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_cell_measurement_theta_min      4.8680
_cell_volume                     3946.9(4)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      284.94(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -117.00  -32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343  165.0000  -92.5273 85

  2 omega  -41.00   26.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343   37.0000  -30.0000 67

  3 omega  -43.00   23.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343   37.0000 -150.0000 66

  4 omega   57.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2343 -125.0000 -150.0000 40

  5 omega   37.00  127.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -61.0000 -180.0000 90

  6 omega   29.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000  -30.0000 62

  7 omega   61.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000    0.0000 29

  8 omega   51.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000   60.0000 26

  9 omega   53.00  154.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   15.0000  -60.0000 101

 10 omega   77.00  149.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  178.0000 -150.0000 72

 11 omega   87.00  127.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  178.0000  -90.0000 40
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0972592000
_diffrn_orient_matrix_UB_12      0.0909153000
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_diffrn_orient_matrix_UB_21      -0.0733601000
_diffrn_orient_matrix_UB_22      0.0663045000
_diffrn_orient_matrix_UB_23      -0.0356530000
_diffrn_orient_matrix_UB_31      -0.0515962000
_diffrn_orient_matrix_UB_32      0.0769578000
_diffrn_orient_matrix_UB_33      0.0366672000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_unetI/netI     0.1175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            14316
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         4.023
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.190
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_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.00129(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
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_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1078
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_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0687P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.2029
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4365
_reflns_number_total             7045
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc06531k2.cif
_cod_data_source_block           g170526e
_cod_database_code               7120677
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N S'
_reflns_odcompleteness_completeness 99.91
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), N5(H5A), N6(H6A), C2(H2A), C3(H3A), C5(H5), C6(H6), C19(H19),
 C20(H20), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C24(H24A,
 H24B,H24C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C),
 C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C)
;
_olex2_submission_special_instructions 'No special instructions were received'