#------------------------------------------------------------------------------
#$Date: 2019-11-10 07:20:49 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225832 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/56/4515699.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_4515699
loop_
_publ_author_name
'Tamang, Sem Raj'
'Singh, Arpita'
'Unruh, Daniel K.'
'Findlater, Michael'
_publ_section_title
;
 Nickel-Catalyzed Regioselective 1,4-Hydroboration of N-Heteroarenes
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              6186
_journal_paper_doi               10.1021/acscatal.8b01166
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C24 H32 N2 Ni O4'
_chemical_formula_sum            'C24 H32 N2 Ni O4'
_chemical_formula_weight         471.22
_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   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                108.250(3)
_cell_angle_beta                 93.812(3)
_cell_angle_gamma                94.208(3)
_cell_formula_units_Z            1
_cell_length_a                   7.960(2)
_cell_length_b                   8.085(2)
_cell_length_c                   9.656(2)
_cell_measurement_reflns_used    5386
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.15
_cell_measurement_theta_min      2.23
_cell_volume                     585.9(2)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10024
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.259
_diffrn_reflns_theta_min         2.231
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Purple
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       Block
_exptl_crystal_F_000             250
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0307
_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)+(0.0432P)²+0.3631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0826
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2446
_reflns_number_total             2623
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs8b01166_si_001.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        585.9(3)
_cod_database_code               4515699
_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.
;
_shelx_estimated_absorpt_t_min   0.854
_shelx_estimated_absorpt_t_max   0.908
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
_atom_site_refinement_flags_occupancy
Ni1 Ni 0.5000 0.5000 1.0000 0.01709(11) Uani 1 2 d S . P
O1 O 0.35787(15) 0.28991(15) 0.85796(13) 0.0206(3) Uani 1 1 d . . .
O2 O 0.31195(15) 0.65647(15) 1.00179(13) 0.0198(3) Uani 1 1 d . . .
N1 N 0.59149(18) 0.56933(19) 0.82404(16) 0.0191(3) Uani 1 1 d . . .
C1 C 0.2134(2) 0.2961(2) 0.79861(18) 0.0188(3) Uani 1 1 d . . .
C2 C 0.1248(2) 0.4440(2) 0.82007(19) 0.0226(4) Uani 1 1 d . . .
H2 H 0.0194 0.4292 0.7632 0.027 Uiso 1 1 calc R U .
C3 C 0.1770(2) 0.6125(2) 0.91797(18) 0.0189(3) Uani 1 1 d . . .
C4 C 0.1310(2) 0.1236(2) 0.6936(2) 0.0270(4) Uani 1 1 d . . .
H4A H 0.0254 0.1431 0.6455 0.041 Uiso 1 1 calc R U .
H4B H 0.1064 0.0420 0.7479 0.041 Uiso 1 1 calc R U .
H4C H 0.2079 0.0742 0.6196 0.041 Uiso 1 1 calc R U .
C5 C 0.0624(2) 0.7554(2) 0.9235(2) 0.0262(4) Uani 1 1 d . . .
H5A H 0.1132 0.8654 0.9956 0.039 Uiso 1 1 calc R U .
H5B H -0.0481 0.7228 0.9518 0.039 Uiso 1 1 calc R U .
H5C H 0.0479 0.7705 0.8268 0.039 Uiso 1 1 calc R U .
C6 C 0.5883(2) 0.7323(2) 0.81752(19) 0.0201(3) Uani 1 1 d . . .
H6 H 0.5469 0.8179 0.8962 0.024 Uiso 1 1 calc R U .
C7 C 0.6425(2) 0.7822(2) 0.70144(19) 0.0203(3) Uani 1 1 d . . .
C8 C 0.7044(2) 0.6547(2) 0.58835(19) 0.0202(3) Uani 1 1 d . . .
H8 H 0.7422 0.6836 0.5068 0.024 Uiso 1 1 calc R U .
C9 C 0.7114(2) 0.4856(2) 0.59375(18) 0.0196(3) Uani 1 1 d . . .
C10 C 0.6518(2) 0.4494(2) 0.71393(18) 0.0194(3) Uani 1 1 d . . .
H10 H 0.6540 0.3339 0.7184 0.023 Uiso 1 1 calc R U .
C11 C 0.6317(3) 0.9663(2) 0.6987(2) 0.0264(4) Uani 1 1 d . . .
H11A H 0.5864 0.9632 0.6010 0.040 Uiso 1 1 calc R U .
H11B H 0.7449 1.0301 0.7222 0.040 Uiso 1 1 calc R U .
H11C H 0.5569 1.0253 0.7712 0.040 Uiso 1 1 calc R U .
C12 C 0.7800(2) 0.3456(2) 0.4738(2) 0.0250(4) Uani 1 1 d . . .
H12A H 0.7435 0.3571 0.3786 0.037 Uiso 1 1 calc R U .
H12B H 0.7371 0.2300 0.4766 0.037 Uiso 1 1 calc R U .
H12C H 0.9039 0.3588 0.4884 0.037 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 0.0033 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'
Ni Ni 0.3393 1.1124 '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
O1 Ni1 O1 180.0 . 2_667
O1 Ni1 O2 88.00(5) . 2_667
O1 Ni1 O2 92.00(5) 2_667 2_667
O1 Ni1 O2 92.00(5) . .
O1 Ni1 O2 88.00(5) 2_667 .
O2 Ni1 O2 180.0 2_667 .
O1 Ni1 N1 89.56(6) . 2_667
O1 Ni1 N1 90.44(5) 2_667 2_667
O2 Ni1 N1 88.88(5) 2_667 2_667
O2 Ni1 N1 91.13(5) . 2_667
O1 Ni1 N1 90.44(5) . .
O1 Ni1 N1 89.56(6) 2_667 .
O2 Ni1 N1 91.12(5) 2_667 .
O2 Ni1 N1 88.87(5) . .
N1 Ni1 N1 180.00(3) 2_667 .
C1 O1 Ni1 124.07(11) . .
C3 O2 Ni1 124.61(11) . .
C10 N1 C6 118.31(15) . .
C10 N1 Ni1 120.30(11) . .
C6 N1 Ni1 121.39(11) . .
O1 C1 C2 126.76(16) . .
O1 C1 C4 115.16(15) . .
C2 C1 C4 118.08(16) . .
C1 C2 C3 126.16(17) . .
C1 C2 H2 116.9 . .
C3 C2 H2 116.9 . .
O2 C3 C2 125.82(15) . .
O2 C3 C5 116.40(15) . .
C2 C3 C5 117.78(16) . .
C1 C4 H4A 109.5 . .
C1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C3 C5 H5A 109.5 . .
C3 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C3 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
N1 C6 C7 123.27(15) . .
N1 C6 H6 118.4 . .
C7 C6 H6 118.4 . .
C6 C7 C8 117.16(15) . .
C6 C7 C11 120.76(15) . .
C8 C7 C11 122.07(16) . .
C9 C8 C7 120.61(16) . .
C9 C8 H8 119.7 . .
C7 C8 H8 119.7 . .
C10 C9 C8 117.39(15) . .
C10 C9 C12 120.89(15) . .
C8 C9 C12 121.71(16) . .
N1 C10 C9 123.25(15) . .
N1 C10 H10 118.4 . .
C9 C10 H10 118.4 . .
C7 C11 H11A 109.5 . .
C7 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C7 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O1 2.0245(13) .
Ni1 O1 2.0245(13) 2_667
Ni1 O2 2.0270(12) 2_667
Ni1 O2 2.0270(12) .
Ni1 N1 2.1053(15) 2_667
Ni1 N1 2.1053(15) .
O1 C1 1.262(2) .
O2 C3 1.259(2) .
N1 C10 1.338(2) .
N1 C6 1.340(2) .
C1 C2 1.399(2) .
C1 C4 1.515(2) .
C2 C3 1.408(2) .
C2 H2 0.9500 .
C3 C5 1.513(2) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 C7 1.388(2) .
C6 H6 0.9500 .
C7 C8 1.393(2) .
C7 C11 1.505(2) .
C8 C9 1.390(2) .
C8 H8 0.9500 .
C9 C10 1.386(2) .
C9 C12 1.508(2) .
C10 H10 0.9500 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
