#------------------------------------------------------------------------------
#$Date: 2019-11-26 07:03:16 +0200 (Tue, 26 Nov 2019) $
#$Revision: 242900 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/30/4133053.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_4133053
loop_
_publ_author_name
'Wang, Kuai'
'Ding, Zhengtian'
'Zhou, Zhijun'
'Kong, Wangqing'
_publ_section_title
;
 Ni-Catalyzed Enantioselective Reductive Diarylation of Activated Alkenes
 by Domino Cyclization/Cross-Coupling.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12364
_journal_page_last               12368
_journal_paper_doi               10.1021/jacs.8b08190
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C76 H84 N4 O4'
_chemical_formula_weight         1117.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.119(2)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   9.0808(3)
_cell_length_b                   14.9109(4)
_cell_length_c                   12.3558(4)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.5398
_cell_measurement_theta_min      2.2709
_cell_volume                     1607.24(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11885
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        62.785
_diffrn_reflns_theta_max         62.785
_diffrn_reflns_theta_min         3.724
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_T_max  0.788
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       acicular
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1773 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         4846
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0427
_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/[σ²(Fo²)+(0.0658P)²+0.0042P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1112
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    0.894
_reflns_Friedel_fraction_max     0.894
_reflns_number_gt                4309
_reflns_number_total             4846
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b08190_si_001.cif
_cod_data_source_block           cu_WK_116_4_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4133053
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_exptl_absorpt_special_details
;
 ?
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.7258(3) 0.12519(18) 0.7303(3) 0.0880(8) Uani 1 1 d . .
N1 N 0.6802(3) 0.17874(16) 0.5510(2) 0.0563(6) Uani 1 1 d . .
C1 C 0.6853(5) 0.0938(3) 0.4945(4) 0.0843(12) Uani 1 1 d . .
H1 H 0.6933 0.0456 0.5472 0.126 Uiso 1 1 calc R U
H2 H 0.7726 0.0930 0.4650 0.126 Uiso 1 1 calc R U
H3 H 0.5934 0.0868 0.4338 0.126 Uiso 1 1 calc R U
C2 C 0.6567(3) 0.26235(19) 0.4979(2) 0.0477(6) Uani 1 1 d . .
C3 C 0.6330(3) 0.2817(3) 0.3849(3) 0.0640(9) Uani 1 1 d . .
H4 H 0.6335 0.2369 0.3327 0.077 Uiso 1 1 calc R U
C4 C 0.6084(4) 0.3709(3) 0.3529(3) 0.0694(9) Uani 1 1 d . .
H5 H 0.5909 0.3864 0.2775 0.083 Uiso 1 1 calc R U
C5 C 0.6096(3) 0.4361(3) 0.4301(3) 0.0676(9) Uani 1 1 d . .
H6 H 0.5927 0.4953 0.4063 0.081 Uiso 1 1 calc R U
C6 C 0.6353(3) 0.4162(2) 0.5432(3) 0.0534(7) Uani 1 1 d . .
H7 H 0.6365 0.4615 0.5951 0.064 Uiso 1 1 calc R U
C7 C 0.6590(3) 0.32836(18) 0.5777(2) 0.0441(6) Uani 1 1 d . .
C8 C 0.6927(3) 0.28638(19) 0.6924(2) 0.0472(6) Uani 1 1 d . .
C9 C 0.7021(3) 0.1870(2) 0.6644(3) 0.0570(8) Uani 1 1 d . .
C10 C 0.8483(3) 0.3165(3) 0.7692(3) 0.0662(8) Uani 1 1 d . .
H8 H 0.9263 0.3068 0.7315 0.099 Uiso 1 1 calc R U
H9 H 0.8721 0.2825 0.8378 0.099 Uiso 1 1 calc R U
H10 H 0.8440 0.3791 0.7862 0.099 Uiso 1 1 calc R U
C11 C 0.5697(3) 0.3037(2) 0.7546(2) 0.0521(7) Uani 1 1 d . .
H11 H 0.6004 0.2726 0.8264 0.062 Uiso 1 1 calc R U
H12 H 0.5692 0.3674 0.7707 0.062 Uiso 1 1 calc R U
C12 C 0.4072(3) 0.27574(19) 0.6946(2) 0.0466(6) Uani 1 1 d . .
C13 C 0.3532(3) 0.1911(2) 0.7117(2) 0.0512(7) Uani 1 1 d . .
H21 H 0.4196 0.1503 0.7576 0.061 Uiso 1 1 calc R U
C14 C 0.2019(3) 0.1662(2) 0.6617(3) 0.0536(7) Uani 1 1 d . .
C15 C 0.1429(4) 0.0758(2) 0.6836(4) 0.0753(10) Uani 1 1 d . .
H18 H 0.0505 0.0831 0.7060 0.113 Uiso 1 1 calc R U
H19 H 0.2187 0.0462 0.7427 0.113 Uiso 1 1 calc R U
H20 H 0.1219 0.0403 0.6162 0.113 Uiso 1 1 calc R U
C16 C 0.1062(3) 0.2272(2) 0.5923(3) 0.0542(7) Uani 1 1 d . .
H17 H 0.0051 0.2110 0.5582 0.065 Uiso 1 1 calc R U
C17 C 0.1555(3) 0.3116(2) 0.5717(3) 0.0535(7) Uani 1 1 d . .
C18 C 0.0486(4) 0.3761(3) 0.4950(3) 0.0710(9) Uani 1 1 d . .
H14 H 0.1032 0.4299 0.4879 0.106 Uiso 1 1 calc R U
H15 H -0.0345 0.3905 0.5259 0.106 Uiso 1 1 calc R U
H16 H 0.0088 0.3492 0.4221 0.106 Uiso 1 1 calc R U
C19 C 0.3069(3) 0.33496(19) 0.6242(2) 0.0490(6) Uani 1 1 d . .
H13 H 0.3417 0.3916 0.6118 0.059 Uiso 1 1 calc R U
O2 O 0.7028(3) 0.54534(17) 0.7773(2) 0.0802(7) Uani 1 1 d . .
N2 N 0.7336(3) 0.6950(2) 0.7504(2) 0.0582(6) Uani 1 1 d . .
C20 C 0.7271(4) 0.6912(4) 0.6321(3) 0.0914(14) Uani 1 1 d . .
H22 H 0.8270 0.7031 0.6232 0.137 Uiso 1 1 calc R U
H23 H 0.6560 0.7353 0.5915 0.137 Uiso 1 1 calc R U
H24 H 0.6941 0.6326 0.6031 0.137 Uiso 1 1 calc R U
C21 C 0.7572(3) 0.7727(2) 0.8169(3) 0.0569(8) Uani 1 1 d . .
C22 C 0.7659(4) 0.8606(3) 0.7835(4) 0.0835(13) Uani 1 1 d . .
H25 H 0.7586 0.8749 0.7089 0.100 Uiso 1 1 calc R U
C23 C 0.7856(4) 0.9256(3) 0.8639(6) 0.1042(18) Uani 1 1 d . .
H26 H 0.7902 0.9852 0.8431 0.125 Uiso 1 1 calc R U
C24 C 0.7988(4) 0.9056(3) 0.9733(6) 0.0954(16) Uani 1 1 d . .
H27 H 0.8130 0.9517 1.0259 0.114 Uiso 1 1 calc R U
C25 C 0.7914(3) 0.8167(3) 1.0086(4) 0.0735(10) Uani 1 1 d . .
H28 H 0.8007 0.8031 1.0837 0.088 Uiso 1 1 calc R U
C26 C 0.7697(3) 0.7502(2) 0.9280(3) 0.0501(7) Uani 1 1 d . .
C27 C 0.7562(3) 0.65030(19) 0.9355(2) 0.0480(6) Uani 1 1 d . .
C28 C 0.7259(3) 0.6212(2) 0.8133(3) 0.0510(7) Uani 1 1 d . .
C29 C 0.9099(3) 0.6082(3) 1.0025(3) 0.0683(9) Uani 1 1 d . .
H29 H 0.9901 0.6281 0.9714 0.102 Uiso 1 1 calc R U
H30 H 0.9023 0.5441 0.9978 0.102 Uiso 1 1 calc R U
H32 H 0.9328 0.6264 1.0799 0.102 Uiso 1 1 calc R U
C30 C 0.6270(3) 0.6174(2) 0.9847(3) 0.0577(7) Uani 1 1 d . .
H33 H 0.6291 0.5524 0.9863 0.069 Uiso 1 1 calc R U
H34 H 0.6497 0.6379 1.0621 0.069 Uiso 1 1 calc R U
C31 C 0.4664(3) 0.64691(19) 0.9236(2) 0.0503(7) Uani 1 1 d . .
C32 C 0.4143(3) 0.7321(2) 0.9394(3) 0.0541(7) Uani 1 1 d . .
H35 H 0.4815 0.7724 0.9855 0.065 Uiso 1 1 calc R U
C33 C 0.2652(3) 0.7588(2) 0.8884(3) 0.0581(7) Uani 1 1 d . .
C34 C 0.2114(5) 0.8519(3) 0.9073(4) 0.0840(11) Uani 1 1 d . .
H36 H 0.2977 0.8874 0.9471 0.126 Uiso 1 1 calc R U
H37 H 0.1391 0.8481 0.9509 0.126 Uiso 1 1 calc R U
H38 H 0.1634 0.8793 0.8360 0.126 Uiso 1 1 calc R U
C35 C 0.1663(3) 0.6974(2) 0.8209(3) 0.0623(8) Uani 1 1 d . .
H39 H 0.0656 0.7143 0.7867 0.075 Uiso 1 1 calc R U
C36 C 0.2128(3) 0.6120(2) 0.8029(3) 0.0618(8) Uani 1 1 d . .
C37 C 0.3640(4) 0.5880(2) 0.8549(3) 0.0592(8) Uani 1 1 d . .
H43 H 0.3973 0.5308 0.8432 0.071 Uiso 1 1 calc R U
C38 C 0.1011(5) 0.5457(3) 0.7320(4) 0.0913(13) Uani 1 1 d . .
H40 H 0.0294 0.5271 0.7719 0.137 Uiso 1 1 calc R U
H41 H 0.1560 0.4944 0.7168 0.137 Uiso 1 1 calc R U
H42 H 0.0468 0.5735 0.6622 0.137 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C9 N1 C2 111.2(2)
C9 N1 C1 123.8(3)
C2 N1 C1 125.0(3)
N1 C1 H1 109.5
N1 C1 H2 109.5
H1 C1 H2 109.5
N1 C1 H3 109.5
H1 C1 H3 109.5
H2 C1 H3 109.5
C3 C2 C7 122.4(3)
C3 C2 N1 128.4(3)
C7 C2 N1 109.2(2)
C2 C3 C4 117.1(3)
C2 C3 H4 121.4
C4 C3 H4 121.4
C5 C4 C3 121.0(3)
C5 C4 H5 119.5
C3 C4 H5 119.5
C4 C5 C6 121.4(3)
C4 C5 H6 119.3
C6 C5 H6 119.3
C7 C6 C5 119.0(3)
C7 C6 H7 120.5
C5 C6 H7 120.5
C6 C7 C2 119.0(3)
C6 C7 C8 131.5(3)
C2 C7 C8 109.5(2)
C7 C8 C9 101.6(2)
C7 C8 C10 111.9(2)
C9 C8 C10 108.9(2)
C7 C8 C11 114.5(2)
C9 C8 C11 111.6(2)
C10 C8 C11 108.2(2)
O1 C9 N1 124.8(3)
O1 C9 C8 126.7(3)
N1 C9 C8 108.5(3)
C8 C10 H8 109.5
C8 C10 H9 109.5
H8 C10 H9 109.5
C8 C10 H10 109.5
H8 C10 H10 109.5
H9 C10 H10 109.5
C12 C11 C8 116.8(2)
C12 C11 H11 108.1
C8 C11 H11 108.1
C12 C11 H12 108.1
C8 C11 H12 108.1
H11 C11 H12 107.3
C19 C12 C13 118.3(2)
C19 C12 C11 120.8(3)
C13 C12 C11 120.8(3)
C14 C13 C12 121.4(3)
C14 C13 H21 119.3
C12 C13 H21 119.3
C16 C14 C13 118.3(3)
C16 C14 C15 120.6(3)
C13 C14 C15 121.1(3)
C14 C15 H18 109.5
C14 C15 H19 109.5
H18 C15 H19 109.5
C14 C15 H20 109.5
H18 C15 H20 109.5
H19 C15 H20 109.5
C14 C16 C17 122.3(3)
C14 C16 H17 118.9
C17 C16 H17 118.9
C16 C17 C19 118.1(3)
C16 C17 C18 120.9(3)
C19 C17 C18 121.0(3)
C17 C18 H14 109.5
C17 C18 H15 109.5
H14 C18 H15 109.5
C17 C18 H16 109.5
H14 C18 H16 109.5
H15 C18 H16 109.5
C12 C19 C17 121.6(3)
C12 C19 H13 119.2
C17 C19 H13 119.2
C28 N2 C21 110.9(2)
C28 N2 C20 123.4(3)
C21 N2 C20 125.6(3)
N2 C20 H22 109.5
N2 C20 H23 109.5
H22 C20 H23 109.5
N2 C20 H24 109.5
H22 C20 H24 109.5
H23 C20 H24 109.5
C22 C21 C26 121.9(4)
C22 C21 N2 128.3(4)
C26 C21 N2 109.8(3)
C23 C22 C21 117.6(5)
C23 C22 H25 121.2
C21 C22 H25 121.2
C24 C23 C22 121.8(4)
C24 C23 H26 119.1
C22 C23 H26 119.1
C23 C24 C25 121.2(4)
C23 C24 H27 119.4
C25 C24 H27 119.4
C26 C25 C24 117.6(4)
C26 C25 H28 121.2
C24 C25 H28 121.2
C25 C26 C21 119.8(3)
C25 C26 C27 131.8(3)
C21 C26 C27 108.4(3)
C26 C27 C28 102.5(2)
C26 C27 C30 115.1(2)
C28 C27 C30 110.7(2)
C26 C27 C29 111.1(2)
C28 C27 C29 107.7(2)
C30 C27 C29 109.4(2)
O2 C28 N2 125.2(3)
O2 C28 C27 126.5(3)
N2 C28 C27 108.2(3)
C27 C29 H29 109.5
C27 C29 H30 109.5
H29 C29 H30 109.5
C27 C29 H32 109.5
H29 C29 H32 109.5
H30 C29 H32 109.5
C31 C30 C27 116.4(2)
C31 C30 H33 108.2
C27 C30 H33 108.2
C31 C30 H34 108.2
C27 C30 H34 108.2
H33 C30 H34 107.3
C37 C31 C32 118.0(3)
C37 C31 C30 120.8(3)
C32 C31 C30 121.1(3)
C33 C32 C31 121.9(3)
C33 C32 H35 119.1
C31 C32 H35 119.1
C32 C33 C35 118.2(3)
C32 C33 C34 120.7(3)
C35 C33 C34 121.1(3)
C33 C34 H36 109.5
C33 C34 H37 109.5
H36 C34 H37 109.5
C33 C34 H38 109.5
H36 C34 H38 109.5
H37 C34 H38 109.5
C36 C35 C33 122.0(3)
C36 C35 H39 119.0
C33 C35 H39 119.0
C35 C36 C37 118.0(3)
C35 C36 C38 120.8(3)
C37 C36 C38 121.2(3)
C31 C37 C36 121.9(3)
C31 C37 H43 119.0
C36 C37 H43 119.0
C36 C38 H40 109.5
C36 C38 H41 109.5
H40 C38 H41 109.5
C36 C38 H42 109.5
H40 C38 H42 109.5
H41 C38 H42 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.209(4)
N1 C9 1.366(4)
N1 C2 1.397(4)
N1 C1 1.453(4)
C1 H1 0.9600
C1 H2 0.9600
C1 H3 0.9600
C2 C3 1.383(5)
C2 C7 1.389(4)
C3 C4 1.388(6)
C3 H4 0.9300
C4 C5 1.359(6)
C4 H5 0.9300
C5 C6 1.384(5)
C5 H6 0.9300
C6 C7 1.375(4)
C6 H7 0.9300
C7 C8 1.501(4)
C8 C9 1.530(5)
C8 C10 1.535(4)
C8 C11 1.544(4)
C10 H8 0.9600
C10 H9 0.9600
C10 H10 0.9600
C11 C12 1.514(4)
C11 H11 0.9700
C11 H12 0.9700
C12 C19 1.388(4)
C12 C13 1.392(4)
C13 C14 1.391(4)
C13 H21 0.9300
C14 C16 1.380(5)
C14 C15 1.503(5)
C15 H18 0.9600
C15 H19 0.9600
C15 H20 0.9600
C16 C17 1.383(4)
C16 H17 0.9300
C17 C19 1.391(4)
C17 C18 1.502(5)
C18 H14 0.9600
C18 H15 0.9600
C18 H16 0.9600
C19 H13 0.9300
O2 C28 1.212(4)
N2 C28 1.360(4)
N2 C21 1.401(4)
N2 C20 1.447(4)
C20 H22 0.9600
C20 H23 0.9600
C20 H24 0.9600
C21 C22 1.383(5)
C21 C26 1.387(5)
C22 C23 1.363(8)
C22 H25 0.9300
C23 C24 1.357(8)
C23 H26 0.9300
C24 C25 1.402(7)
C24 H27 0.9300
C25 C26 1.380(5)
C25 H28 0.9300
C26 C27 1.500(4)
C27 C28 1.521(4)
C27 C30 1.544(4)
C27 C29 1.545(4)
C29 H29 0.9600
C29 H30 0.9600
C29 H32 0.9600
C30 C31 1.510(4)
C30 H33 0.9700
C30 H34 0.9700
C31 C37 1.385(4)
C31 C32 1.388(4)
C32 C33 1.383(4)
C32 H35 0.9300
C33 C35 1.387(5)
C33 C34 1.511(5)
C34 H36 0.9600
C34 H37 0.9600
C34 H38 0.9600
C35 C36 1.379(5)
C35 H39 0.9300
C36 C37 1.392(5)
C36 C38 1.510(5)
C37 H43 0.9300
C38 H40 0.9600
C38 H41 0.9600
C38 H42 0.9600
