Nickel-Catalyzed Dearomative trans-1,2-Carboamination.
Hernandez, Lucas W.; Klöckner, Ulrich; Pospech, Jola; Hauss, Lilian; Sarlah, David; Journal of the American Chemical Society 140 (2018) 4503–4507; doi:10.1021/jacs.8b01726

data_4132123
_publ_section_title
;
 Nickel-Catalyzed Dearomative trans-1,2-Carboamination.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4503
_journal_page_last               4507
_journal_paper_doi               10.1021/jacs.8b01726
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C18 H23 N3 O2 Si'
_chemical_formula_sum            'C18 H23 N3 O2 Si'
_chemical_formula_weight         341.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-02-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.021(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5544(18)
_cell_length_b                   6.1514(9)
_cell_length_c                   25.784(4)
_cell_measurement_reflns_used    7766
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      2.31
_cell_volume                     1830.1(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEXII CCD area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            48329
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.438
_diffrn_reflns_theta_min         3.165
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0685 before and 0.0611 after correction. The Ratio of minimum to maximum transmission is 0.9272. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_recrystallization_method
'Single crystal was obtained by a slow vapor diffusion using diethyl ether and hexane.'
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0370P)^2^+1.0150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3513
_reflns_number_total             4553
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b01726_si_003.cif
_cod_data_source_block           dm77j_0m
_cod_original_cell_volume        1830.0(5)
_cod_database_code               4132123
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C)
;
_shelx_res_checksum              46191
_shelx_hkl_checksum              75516
_olex2_exptl_crystal_mounting_method
'the crystal was mounted on a loop with spindle axis of -3 2 -3.'
_olex2_submission_original_sample_id lwh-4-1105-4
_olex2_submission_special_instructions 'No special instructions were received'