Nickel-promoted oxidative domino C<sub>sp3</sub>-H/N-H bond double-isocyanide insertion reaction to construct pyrrolin-2-ones.
Wen, Li-Rong; Wang, Ning-Ning; Du, Wu-Bo; Ma, Qiang; Zhang, Lin-Bao; Li, Ming; Organic & biomolecular chemistry 19 (2021) 2895–2900; doi:10.1039/d1ob00139f

data_7157929
_publ_section_title
;
 Nickel-promoted oxidative domino C<sub>sp3</sub>-H/N-H bond
 double-isocyanide insertion reaction to construct pyrrolin-2-ones.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2895
_journal_page_last               2900
_journal_paper_doi               10.1039/d1ob00139f
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C23 H27 Br N4 O'
_chemical_formula_sum            'C23 H27 Br N4 O'
_chemical_formula_weight         455.39
_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   mixed
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc1ls23k
_audit_creation_date             2016-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-06-01 deposited with the CCDC.	2021-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                77.929(5)
_cell_angle_beta                 76.867(5)
_cell_angle_gamma                88.501(5)
_cell_formula_units_Z            4
_cell_length_a                   11.5777(16)
_cell_length_b                   12.8278(18)
_cell_length_c                   15.3442(19)
_cell_measurement_reflns_used    6233
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4819
_cell_measurement_theta_min      2.3505
_cell_volume                     2169.6(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 40.0747
	          2theta: -19.7214
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 40.0747
	          2theta: -19.7214
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0636
_diffrn_orient_matrix_UB_12      0.0271
_diffrn_orient_matrix_UB_13      0.0556
_diffrn_orient_matrix_UB_21      -0.0561
_diffrn_orient_matrix_UB_22      -0.0366
_diffrn_orient_matrix_UB_23      -0.0434
_diffrn_orient_matrix_UB_31      0.0286
_diffrn_orient_matrix_UB_32      -0.0524
_diffrn_orient_matrix_UB_33      0.0335
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18414
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         1.906
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    1.916
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.528
_exptl_crystal_size_mid          0.436
_exptl_crystal_size_min          0.206
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     531
_refine_ls_number_reflns         9763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0383P)^2^+1.7669P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8202
_reflns_number_total             9763
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00139f2.cif
_cod_data_source_block           sa4820a
_cod_depositor_comments          'Adding full bibliography for 7157929.cif.'
_cod_database_code               7157929
_diffrn_number_total             9767
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C12(H12), C6A(H6A), C12A(H12A)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
  C7A(H7AA,H7AB), C8A(H8AA,H8AB), C9A(H9AA,H9AB), C10A(H10C,H10D), C11A(H11C,
 H11D), C13A(H13C,H13D), C14A(H14C,H14D), C15A(H15C,H15D), C16A(H16C,H16D),
 C17A(H17C,H17D)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C22(H22), C23(H23), C19A(H19A), C20A(H20A), C22A(H22A),
 C23A(H23A)
;
_shelx_res_checksum              66937
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'