#------------------------------------------------------------------------------
#$Date: 2019-11-10 07:21:30 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225836 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/57/4515702.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_4515702
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 H28 N2 Ni O8'
_chemical_formula_sum            'C24 H28 N2 Ni O8'
_chemical_formula_weight         531.19
_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                101.952(14)
_cell_angle_beta                 99.095(8)
_cell_angle_gamma                99.806(9)
_cell_formula_units_Z            1
_cell_length_a                   6.736(3)
_cell_length_b                   8.129(3)
_cell_length_c                   11.969(5)
_cell_measurement_reflns_used    7304
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.16
_cell_measurement_theta_min      2.61
_cell_volume                     619.0(4)
_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 1.000
_diffrn_measured_fraction_theta_max 0.995
_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  0.0251
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13805
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.270
_diffrn_reflns_theta_min         1.775
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       blade
_exptl_crystal_F_000             278
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0243
_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)+(0.0275P)²+0.3187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0614
_refine_ls_wR_factor_ref         0.0626
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2598
_reflns_number_total             2780
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs8b01166_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4515702
_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   0.688
_shelx_estimated_absorpt_t_max   0.925
_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 0.5000 0.01240(8) Uani 1 2 d S . P
O1 O 0.73350(14) 0.66150(12) 0.62215(8) 0.0158(2) Uani 1 1 d . . .
O2 O 0.33624(14) 0.68507(12) 0.49804(8) 0.01504(19) Uani 1 1 d . . .
O3 O 0.50536(16) 0.73984(14) 0.00704(9) 0.0224(2) Uani 1 1 d . . .
O4 O 0.24428(16) 0.68556(16) 0.09766(10) 0.0271(2) Uani 1 1 d . . .
N1 N 0.63057(17) 0.56902(14) 0.36254(10) 0.0139(2) Uani 1 1 d . . .
C1 C 0.7153(2) 0.80209(17) 0.68395(12) 0.0155(3) Uani 1 1 d . . .
C2 C 0.5521(2) 0.88603(18) 0.66393(12) 0.0173(3) Uani 1 1 d . . .
H2 H 0.5600 0.9929 0.7167 0.021 Uiso 1 1 calc R U .
C3 C 0.3779(2) 0.82675(17) 0.57308(11) 0.0144(3) Uani 1 1 d . . .
C4 C 0.8848(2) 0.8835(2) 0.78999(13) 0.0230(3) Uani 1 1 d . . .
H4A H 0.8675 0.9990 0.8250 0.035 Uiso 1 1 calc R U .
H4B H 1.0186 0.8914 0.7667 0.035 Uiso 1 1 calc R U .
H4C H 0.8781 0.8128 0.8470 0.035 Uiso 1 1 calc R U .
C5 C 0.2234(2) 0.93990(18) 0.56193(13) 0.0200(3) Uani 1 1 d . . .
H5A H 0.2636 1.0423 0.6270 0.030 Uiso 1 1 calc R U .
H5B H 0.0870 0.8760 0.5634 0.030 Uiso 1 1 calc R U .
H5C H 0.2193 0.9749 0.4882 0.030 Uiso 1 1 calc R U .
C6 C 0.5067(2) 0.60047(17) 0.27442(12) 0.0149(3) Uani 1 1 d . . .
H6 H 0.3638 0.5848 0.2748 0.018 Uiso 1 1 calc R U .
C7 C 0.5762(2) 0.65488(17) 0.18230(12) 0.0149(3) Uani 1 1 d . . .
C8 C 0.7855(2) 0.67654(18) 0.18123(12) 0.0183(3) Uani 1 1 d . . .
H8 H 0.8384 0.7118 0.1190 0.022 Uiso 1 1 calc R U .
C9 C 0.9144(2) 0.64542(19) 0.27303(13) 0.0198(3) Uani 1 1 d . . .
H9 H 1.0581 0.6607 0.2752 0.024 Uiso 1 1 calc R U .
C10 C 0.8323(2) 0.59182(17) 0.36153(12) 0.0168(3) Uani 1 1 d . . .
H10 H 0.9221 0.5703 0.4240 0.020 Uiso 1 1 calc R U .
C11 C 0.4223(2) 0.69290(17) 0.09272(12) 0.0169(3) Uani 1 1 d . . .
C12 C 0.3636(3) 0.7851(2) -0.08020(13) 0.0270(3) Uani 1 1 d . . .
H12A H 0.4324 0.8070 -0.1436 0.041 Uiso 1 1 calc R U .
H12B H 0.3189 0.8888 -0.0446 0.041 Uiso 1 1 calc R U .
H12C H 0.2437 0.6902 -0.1114 0.041 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
O2 Ni1 O2 180.0 2_666 .
O2 Ni1 O1 91.95(5) 2_666 2_666
O2 Ni1 O1 88.05(5) . 2_666
O2 Ni1 O1 88.05(5) 2_666 .
O2 Ni1 O1 91.95(5) . .
O1 Ni1 O1 180.0 2_666 .
O2 Ni1 N1 90.33(4) 2_666 .
O2 Ni1 N1 89.67(4) . .
O1 Ni1 N1 88.01(5) 2_666 .
O1 Ni1 N1 91.99(5) . .
O2 Ni1 N1 89.67(4) 2_666 2_666
O2 Ni1 N1 90.33(4) . 2_666
O1 Ni1 N1 91.99(5) 2_666 2_666
O1 Ni1 N1 88.01(5) . 2_666
N1 Ni1 N1 180.0 . 2_666
C1 O1 Ni1 123.37(9) . .
C3 O2 Ni1 124.25(9) . .
C11 O3 C12 114.50(12) . .
C6 N1 C10 118.00(12) . .
C6 N1 Ni1 118.03(9) . .
C10 N1 Ni1 123.88(9) . .
O1 C1 C2 125.97(13) . .
O1 C1 C4 115.96(12) . .
C2 C1 C4 118.06(13) . .
C1 C2 C3 126.12(13) . .
C1 C2 H2 116.9 . .
C3 C2 H2 116.9 . .
O2 C3 C2 126.00(12) . .
O2 C3 C5 115.56(12) . .
C2 C3 C5 118.44(12) . .
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 123.25(12) . .
N1 C6 H6 118.4 . .
C7 C6 H6 118.4 . .
C6 C7 C8 118.42(13) . .
C6 C7 C11 117.52(12) . .
C8 C7 C11 124.02(12) . .
C9 C8 C7 118.40(13) . .
C9 C8 H8 120.8 . .
C7 C8 H8 120.8 . .
C10 C9 C8 119.43(13) . .
C10 C9 H9 120.3 . .
C8 C9 H9 120.3 . .
N1 C10 C9 122.49(13) . .
N1 C10 H10 118.8 . .
C9 C10 H10 118.8 . .
O4 C11 O3 123.61(13) . .
O4 C11 C7 124.13(13) . .
O3 C11 C7 112.25(12) . .
O3 C12 H12A 109.5 . .
O3 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
O3 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 O2 2.0130(11) 2_666
Ni1 O2 2.0130(11) .
Ni1 O1 2.0272(11) 2_666
Ni1 O1 2.0272(11) .
Ni1 N1 2.1134(13) .
Ni1 N1 2.1135(13) 2_666
O1 C1 1.2626(17) .
O2 C3 1.2624(17) .
O3 C11 1.3347(17) .
O3 C12 1.4496(18) .
O4 C11 1.2016(18) .
N1 C6 1.3344(18) .
N1 C10 1.3423(18) .
C1 C2 1.4046(19) .
C1 C4 1.513(2) .
C2 C3 1.406(2) .
C2 H2 0.9500 .
C3 C5 1.5099(18) .
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 1.3875(19) .
C6 H6 0.9500 .
C7 C8 1.393(2) .
C7 C11 1.4882(19) .
C8 C9 1.383(2) .
C8 H8 0.9500 .
C9 C10 1.383(2) .
C9 H9 0.9500 .
C10 H10 0.9500 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
