#------------------------------------------------------------------------------
#$Date: 2021-08-03 22:40:35 +0300 (Tue, 03 Aug 2021) $
#$Revision: 267920 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/89/4518946.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4518946
loop_
_publ_author_name
'Zhou, Fang'
'Zhu, Shaolin'
_publ_section_title
;
 Catalytic Asymmetric Hydroalkylation of α,β-Unsaturated Amides Enabled
 by Regio-Reversed and Enantiodifferentiating syn-Hydronickellation
;
_journal_issue                   14
_journal_name_full               'ACS Catalysis'
_journal_page_first              8766
_journal_page_last               8773
_journal_paper_doi               10.1021/acscatal.1c02299
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H25 N O'
_chemical_formula_sum            'C20 H25 N O'
_chemical_formula_weight         295.41
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-01-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   10.1942(9)
_cell_length_b                   10.1942(9)
_cell_length_c                   14.1934(17)
_cell_measurement_reflns_used    3256
_cell_measurement_temperature    193
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.717
_cell_volume                     1277.4(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0756
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11907
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.31
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1803 before and 0.1114 after correction.
The Ratio of minimum to maximum transmission is 0.8322.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.8(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3648
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0530P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1263
_reflns_number_gt                2847
_reflns_number_total             3648
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs1c02299_si_003.cif
_cod_data_source_block           wpl2021040103_0m_a
_cod_database_code               4518946
_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:
 C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 N002(H002), C6(H6), C16(H16), C20(H20), C5(H5), C2(H2), C17(H17), C4(H4),
 C3(H3), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y, x-y, z+2/3'
3 '-x+y, -x, z+1/3'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O -0.75294(17) -0.36026(18) -0.64641(12) 0.0405(4) Uani 1 1 d . . .
N002 N -0.72215(18) -0.25606(19) -0.50091(13) 0.0316(4) Uani 1 1 d . . .
H002 H -0.6892 -0.2568 -0.4437 0.038 Uiso 1 1 calc R . .
C7 C -0.7049(2) -0.3442(2) -0.56479(16) 0.0291(4) Uani 1 1 d . . .
C1 C -0.7867(2) -0.1621(2) -0.51420(17) 0.0335(5) Uani 1 1 d . . .
C8 C -0.6186(2) -0.4209(2) -0.52935(16) 0.0309(4) Uani 1 1 d . . .
H8 H -0.6534 -0.4559 -0.4635 0.037 Uiso 1 1 calc R . .
C15 C -0.2528(2) -0.6007(2) -0.41103(18) 0.0370(5) Uani 1 1 d . . .
C6 C -0.7542(3) -0.0521(3) -0.4472(2) 0.0452(6) Uani 1 1 d . . .
H6 H -0.6908 -0.0414 -0.3952 0.054 Uiso 1 1 calc R . .
C12 C -0.3540(2) -0.3775(3) -0.49213(18) 0.0408(5) Uani 1 1 d . . .
H12A H -0.3590 -0.4484 -0.5416 0.049 Uiso 1 1 calc R . .
H12B H -0.2468 -0.2967 -0.4862 0.049 Uiso 1 1 calc R . .
C10 C -0.4467(2) -0.3052(2) -0.52516(18) 0.0357(5) Uani 1 1 d . . .
H10 H -0.4320 -0.2268 -0.4774 0.043 Uiso 1 1 calc R . .
C13 C -0.4035(3) -0.4630(3) -0.39929(18) 0.0422(6) Uani 1 1 d . . .
H13A H -0.4973 -0.5610 -0.4099 0.051 Uiso 1 1 calc R . .
H13B H -0.4276 -0.4039 -0.3542 0.051 Uiso 1 1 calc R . .
C16 C -0.1276(3) -0.5522(3) -0.4680(2) 0.0523(7) Uani 1 1 d . . .
H16 H -0.0585 -0.4467 -0.4743 0.063 Uiso 1 1 calc R . .
C9 C -0.6583(3) -0.5601(3) -0.5883(2) 0.0433(6) Uani 1 1 d . . .
H9A H -0.7685 -0.6265 -0.5896 0.065 Uiso 1 1 calc R . .
H9B H -0.6112 -0.6146 -0.5607 0.065 Uiso 1 1 calc R . .
H9C H -0.6207 -0.5290 -0.6527 0.065 Uiso 1 1 calc R . .
C20 C -0.3510(3) -0.7551(3) -0.4055(2) 0.0592(8) Uani 1 1 d . . .
H20 H -0.4385 -0.7924 -0.3669 0.071 Uiso 1 1 calc R . .
C5 C -0.8146(3) 0.0435(3) -0.4559(3) 0.0645(9) Uani 1 1 d . . .
H5 H -0.7921 0.1191 -0.4095 0.077 Uiso 1 1 calc R . .
C11 C -0.3848(3) -0.2231(3) -0.6184(2) 0.0502(6) Uani 1 1 d . . .
H11A H -0.3985 -0.2967 -0.6674 0.075 Uiso 1 1 calc R . .
H11B H -0.2768 -0.1492 -0.6116 0.075 Uiso 1 1 calc R . .
H11C H -0.4395 -0.1705 -0.6364 0.075 Uiso 1 1 calc R . .
C2 C -0.8809(3) -0.1785(3) -0.58983(19) 0.0477(6) Uani 1 1 d . . .
H2 H -0.9048 -0.2548 -0.6359 0.057 Uiso 1 1 calc R . .
C17 C -0.1007(3) -0.6552(4) -0.5165(2) 0.0701(9) Uani 1 1 d . . .
H17 H -0.0132 -0.6198 -0.5549 0.084 Uiso 1 1 calc R . .
C4 C -0.9063(3) 0.0296(3) -0.5306(3) 0.0672(10) Uani 1 1 d . . .
H4 H -0.9465 0.0956 -0.5364 0.081 Uiso 1 1 calc R . .
C3 C -0.9393(3) -0.0813(4) -0.5968(3) 0.0640(9) Uani 1 1 d . . .
H3 H -1.0033 -0.0916 -0.6483 0.077 Uiso 1 1 calc R . .
C14 C -0.2835(3) -0.4931(3) -0.3552(2) 0.0475(6) Uani 1 1 d . . .
H14A H -0.1877 -0.3955 -0.3486 0.057 Uiso 1 1 calc R . .
H14B H -0.3172 -0.5351 -0.2912 0.057 Uiso 1 1 calc R . .
C18 C -0.1993(4) -0.8061(4) -0.5089(3) 0.0703(9) Uani 1 1 d . . .
H18 H -0.1803 -0.8763 -0.5415 0.084 Uiso 1 1 calc R . .
C19 C -0.3248(4) -0.8563(4) -0.4549(3) 0.0759(10) Uani 1 1 d . . .
H19 H -0.3952 -0.9618 -0.4509 0.091 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N002 H002 115.9 . . ?
C7 N002 C1 128.25(19) . . ?
C1 N002 H002 115.9 . . ?
O001 C7 N002 122.88(18) . . ?
O001 C7 C8 122.23(19) . . ?
N002 C7 C8 114.87(19) . . ?
C6 C1 N002 116.9(2) . . ?
C6 C1 C2 120.0(2) . . ?
C2 C1 N002 123.1(2) . . ?
C7 C8 H8 107.5 . . ?
C7 C8 C10 110.21(16) . . ?
C10 C8 H8 107.5 . . ?
C9 C8 C7 110.19(18) . . ?
C9 C8 H8 107.5 . . ?
C9 C8 C10 113.82(18) . . ?
C16 C15 C20 117.1(2) . . ?
C16 C15 C14 122.7(2) . . ?
C20 C15 C14 120.2(2) . . ?
C1 C6 H6 120.1 . . ?
C1 C6 C5 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
H12A C12 H12B 107.4 . . ?
C10 C12 H12A 108.4 . . ?
C10 C12 H12B 108.4 . . ?
C13 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C13 C12 C10 115.63(18) . . ?
C8 C10 H10 107.1 . . ?
C12 C10 C8 112.33(17) . . ?
C12 C10 H10 107.1 . . ?
C11 C10 C8 112.6(2) . . ?
C11 C10 C12 110.13(18) . . ?
C11 C10 H10 107.1 . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C12 C13 C14 113.5(2) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.1(3) . . ?
C17 C16 H16 119.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C20 H20 119.2 . . ?
C19 C20 C15 121.5(3) . . ?
C19 C20 H20 119.2 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 119.9 . . ?
C5 C4 H4 120.5 . . ?
C5 C4 C3 119.1(2) . . ?
C3 C4 H4 120.5 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C15 C14 C13 114.0(2) . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.6 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C20 C19 H19 119.8 . . ?
C18 C19 C20 120.3(3) . . ?
C18 C19 H19 119.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C7 1.236(3) . ?
N002 H002 0.8800 . ?
N002 C7 1.349(3) . ?
N002 C1 1.420(2) . ?
C7 C8 1.524(3) . ?
C1 C6 1.379(3) . ?
C1 C2 1.393(3) . ?
C8 H8 1.0000 . ?
C8 C10 1.549(3) . ?
C8 C9 1.518(3) . ?
C15 C16 1.377(3) . ?
C15 C20 1.382(3) . ?
C15 C14 1.507(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.395(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C10 1.534(3) . ?
C12 C13 1.520(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.524(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.536(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.393(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C20 H20 0.9500 . ?
C20 C19 1.379(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.373(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C2 H2 0.9500 . ?
C2 C3 1.392(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.357(5) . ?
C4 H4 0.9500 . ?
C4 C3 1.376(5) . ?
C3 H3 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C18 H18 0.9500 . ?
C18 C19 1.354(5) . ?
C19 H19 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C7 C8 C10 102.7(2) . . . . ?
O001 C7 C8 C9 -23.7(3) . . . . ?
N002 C7 C8 C10 -76.2(2) . . . . ?
N002 C7 C8 C9 157.40(18) . . . . ?
N002 C1 C6 C5 -179.7(2) . . . . ?
N002 C1 C2 C3 179.8(2) . . . . ?
C7 N002 C1 C6 -162.3(2) . . . . ?
C7 N002 C1 C2 18.6(3) . . . . ?
C7 C8 C10 C12 -178.60(19) . . . . ?
C7 C8 C10 C11 -53.6(2) . . . . ?
C1 N002 C7 O001 -3.8(3) . . . . ?
C1 N002 C7 C8 175.05(17) . . . . ?
C1 C6 C5 C4 -0.1(4) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C15 C16 C17 C18 0.7(5) . . . . ?
C15 C20 C19 C18 1.3(5) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C6 C5 C4 C3 0.6(4) . . . . ?
C12 C13 C14 C15 -66.7(3) . . . . ?
C10 C12 C13 C14 -163.3(2) . . . . ?
C13 C12 C10 C8 -53.8(3) . . . . ?
C13 C12 C10 C11 179.8(2) . . . . ?
C16 C15 C20 C19 0.0(4) . . . . ?
C16 C15 C14 C13 101.8(3) . . . . ?
C16 C17 C18 C19 0.7(5) . . . . ?
C9 C8 C10 C12 -54.2(3) . . . . ?
C9 C8 C10 C11 70.8(2) . . . . ?
C20 C15 C16 C17 -1.0(4) . . . . ?
C20 C15 C14 C13 -79.1(3) . . . . ?
C5 C4 C3 C2 -0.4(4) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C17 C18 C19 C20 -1.7(6) . . . . ?
C14 C15 C16 C17 178.1(3) . . . . ?
C14 C15 C20 C19 -179.1(3) . . . . ?
