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_4515461
_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         'C20 H27 N3 O2'
_chemical_formula_sum            'C20 H27 N3 O2'
_chemical_formula_weight         341.44
_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_creation_date             2018-04-13
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_cell_angle_alpha                81.081(4)
_cell_angle_beta                 81.652(4)
_cell_angle_gamma                73.770(3)
_cell_formula_units_Z            4
_cell_length_a                   9.4368(7)
_cell_length_b                   11.2965(7)
_cell_length_c                   18.1549(11)
_cell_measurement_reflns_used    5549
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.338
_cell_measurement_theta_min      4.533
_cell_volume                     1825.2(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  '?Bruker Pt135'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1296
_diffrn_reflns_av_unetI/netI     0.0866
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23733
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.554
_diffrn_reflns_theta_min         2.478
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0943 before and 0.0742 after correction. The Ratio of minimum to maximum transmission is 0.8546. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         6550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_gt           0.0668
_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^)+(0.0458P)^2^+1.7267P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1557
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4075
_reflns_number_total             6550
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b04516_si_003.cif
_cod_data_source_block           engle110_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               4515461
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.866
_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. Uiso/Uaniso restraints and constraints
Uanis(N5) = Uanis(N5A)
Uanis(N5) = Uanis(C29)
3. Rigid body (RIGU) restrains
 N5A, N5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(H31A)=Sof(C30)=Sof(H30C)=Sof(H30D)=1-FVAR(1)
 Sof(H31)=Sof(C30')=Sof(H30A)=Sof(H30B)=FVAR(1)
 Sof(C29A)=1-FVAR(2)
 Sof(C29)=FVAR(2)
 Sof(N5A)=Sof(H5A)=1-FVAR(3)
 Sof(N5)=Sof(H5)=FVAR(3)
 Fixed Sof: H36(0.5) H36A(0.5) O6(0.5) O8(0.5) C0AA(0.5) H0AA(0.5) H0AB(0.5)
 H0AC(0.5) C3AA(0.5) H3AA(0.5) H3AB(0.5) C2AA(0.5) H2AA(0.5) H2AB(0.5)
 H2AC(0.5) C4AA(0.5) H4AA(0.5) H4AB(0.5) H4AC(0.5) C1AA(0.5) H1AA(0.5)
 H1AB(0.5) C5AA(0.5) H5AA(0.5) H5AB(0.5) H5AC(0.5)
5.a Riding coordinates:
 N5(H5), N5A(H5A)
5.b Ternary CH refined with riding coordinates:
 C12(H12), C17(H17), C31(H31), C31(H31A), C36(H36), C36(H36A)
5.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,
 H16B), C19(H19A,H19B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B),
 C35(H35A,H35B), C30'(H30A,H30B), C30(H30C,H30D), C3AA(H3AA,H3AB), C1AA(H1AA,
 H1AB)
5.d Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C5(H5B), C6(H6), C7(H7), C21(H21), C22(H22),
 C23(H23), C25(H25), C26(H26), C27(H27)
5.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C0AA(H0AA,H0AB,H0AC), C2AA(H2AA,
 H2AB,H2AC), C4AA(H4AA,H4AB,H4AC), C5AA(H5AA,H5AB,H5AC)
;
_shelx_res_checksum              1600
_shelx_hkl_checksum              25408
_olex2_submission_special_instructions 'No special instructions were received'