Directed, Nickel-Catalyzed Umpolung 1,2-Carboamination of Alkenyl Carbonyl Compounds
van der Puyl, Vincent A.; Derosa, Joseph; Engle, Keary M.; ACS Catalysis 9 (2018) 224–; doi:10.1021/acscatal.8b04516

data_4515460
_publ_section_title
;
 Directed, Nickel-Catalyzed Umpolung 1,2-Carboamination of Alkenyl
 Carbonyl Compounds
;
_journal_issue                   1
_journal_name_full               'ACS Catalysis'
_journal_page_first              224
_journal_paper_doi               10.1021/acscatal.8b04516
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C18 H23 N3 O2'
_chemical_formula_sum            'C18 H23 N3 O2'
_chemical_formula_weight         313.39
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-02-21
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.02.02 svn.r3481 for OlexSys, GUI svn.r5470)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.380(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3986(10)
_cell_length_b                   10.1670(12)
_cell_length_c                   18.9640(19)
_cell_measurement_reflns_used    2400
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.000
_cell_measurement_theta_min      2.283
_cell_volume                     1587.5(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX CCD'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'Kappa Four-Circle 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  0.0361
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10446
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.378
_diffrn_reflns_theta_min         2.283
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0452 before and 0.0406 after correction. The Ratio of minimum to maximum transmission is 0.9369. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0489P)^2^+0.3150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1030
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2062
_reflns_number_total             2863
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b04516_si_002.cif
_cod_data_source_block           engle91_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4515460
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C18(H18A,H18B), C17(H17A,H17B), C15(H15A,
 H15B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C6(H6), C3(H3), C2(H2A), C1(H1), C7(H7)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              84902
_shelx_hkl_checksum              99098
_olex2_submission_special_instructions 'No special instructions were received'