#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:11:50 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257065 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/80/4518032.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_4518032
loop_
_publ_author_name
'Talukder, Md Muktadir'
'Cue, John Michael O.'
'Miller, Justin T.'
'Gamage, Prabhath L.'
'Aslam, Amina'
'McCandless, Gregory T.'
'Biewer, Michael C.'
'Stefan, Mihaela C.'
_publ_section_title
;
 Ligand Steric Effects of α-Diimine Nickel(II) and Palladium(II)
 Complexes in the Suzuki-Miyaura Cross-Coupling Reaction.
;
_journal_issue                   37
_journal_name_full               'ACS omega'
_journal_page_first              24018
_journal_page_last               24032
_journal_paper_doi               10.1021/acsomega.0c03415
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C32 H36 Cl2 N4 Ni'
_chemical_formula_sum            'C32 H36 Cl2 N4 Ni'
_chemical_formula_weight         606.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-03-21 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 106.232(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.730(4)
_cell_length_b                   14.003(4)
_cell_length_c                   8.513(2)
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.21
_cell_volume                     1457.0(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL Intrinsic Phasing (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker Kappa D8 Quest CPAD diffractometer (with an Oxford Cryosystems cryostream
cooler)
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'HELIOS optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1225
_diffrn_reflns_av_unetI/netI     0.1653
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            34420
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.585
_diffrn_reflns_theta_min         2.212
_diffrn_source                   'I\mS microfocus tube'
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_T_max  0.6800
_exptl_absorpt_correction_T_min  0.4040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Krause, Herbst-Irmer, Sheldrick, & Stalke;  J. Appl. Cryst. 2015, 48,
3-10)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       plate
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.010
_refine_diff_density_max         1.650
_refine_diff_density_min         -1.477
_refine_diff_density_rms         0.170
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         34420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1483
_refine_ls_R_factor_gt           0.1030
_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)+(0.0377P)²+13.1755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2373
_refine_ls_wR_factor_ref         0.2607
_reflns_Friedel_coverage         0.000
_reflns_number_gt                22811
_reflns_number_total             34420
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao0c03415_si_005.cif
_cod_data_source_block           scd3032_MMT_2M369_twin
_cod_depositor_comments
'Adding full bibliography for 4518031--4518034.cif.'
_cod_original_cell_volume        1456.9(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4518032
_publcif_datablock.id            {ed629f57-79d5-4db6-a5c1-a661c9e9a1c6}
_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.
;
_shelx_estimated_absorpt_t_min   0.779
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.5000 0.5000 0.0117(4) Uani 1 2 d S . P . .
Cl1 Cl 0.56826(17) 0.51904(12) 0.2694(2) 0.0172(5) Uani 1 1 d . . . . .
N1 N 0.4112(6) 0.6266(4) 0.4282(8) 0.0142(14) Uani 1 1 d . . . . .
N2 N 0.6122(5) 0.6069(4) 0.6428(8) 0.0132(14) Uani 1 1 d . . . . .
C1 C 0.3178(7) 0.6385(5) 0.3121(10) 0.0171(17) Uani 1 1 d . . . . .
H1 H 0.2822 0.5840 0.2547 0.020 Uiso 1 1 calc R U . . .
C2 C 0.2692(7) 0.7286(5) 0.2709(11) 0.0227(19) Uani 1 1 d . . . . .
H2 H 0.2018 0.7348 0.1881 0.027 Uiso 1 1 calc R U . . .
C3 C 0.3210(7) 0.8072(5) 0.3521(11) 0.0216(19) Uani 1 1 d . . . . .
H3 H 0.2899 0.8689 0.3266 0.026 Uiso 1 1 calc R U . . .
C4 C 0.4185(7) 0.7961(5) 0.4712(10) 0.0189(18) Uani 1 1 d . . . . .
H4 H 0.4553 0.8499 0.5292 0.023 Uiso 1 1 calc R U . . .
C5 C 0.4625(7) 0.7053(5) 0.5057(10) 0.0149(17) Uani 1 1 d . . . . .
C6 C 0.5659(7) 0.6883(5) 0.6285(10) 0.0169(17) Uani 1 1 d . . . . .
H6 H 0.5995 0.7388 0.6993 0.020 Uiso 1 1 calc R U . . .
C7 C 0.7080(7) 0.5956(5) 0.7787(10) 0.0149(17) Uani 1 1 d . . . . .
C8 C 0.6857(7) 0.5759(5) 0.9274(10) 0.0177(17) Uani 1 1 d . . . . .
H8 H 0.6117 0.5721 0.9300 0.021 Uiso 1 1 calc R U . . .
C9 C 0.7682(7) 0.5618(5) 1.0708(10) 0.0196(18) Uani 1 1 d . . . . .
H9 H 0.7516 0.5476 1.1704 0.024 Uiso 1 1 calc R U . . .
C10 C 0.8752(7) 0.5688(5) 1.0649(10) 0.0192(18) Uani 1 1 d . . . . .
H10 H 0.9333 0.5609 1.1622 0.023 Uiso 1 1 calc R U . . .
C11 C 0.8982(7) 0.5872(5) 0.9195(10) 0.0189(18) Uani 1 1 d . . . . .
H11 H 0.9727 0.5911 0.9193 0.023 Uiso 1 1 calc R U . . .
C12 C 0.8164(7) 0.6006(5) 0.7702(10) 0.0156(17) Uani 1 1 d . . . . .
C13 C 0.8528(7) 0.6152(5) 0.6138(10) 0.0177(18) Uani 1 1 d . . . . .
C14 C 0.9686(7) 0.6588(6) 0.6533(11) 0.026(2) Uani 1 1 d . . . . .
H14A H 0.9867 0.6728 0.5512 0.039 Uiso 1 1 calc R U . . .
H14B H 1.0218 0.6133 0.7182 0.039 Uiso 1 1 calc R U . . .
H14C H 0.9708 0.7179 0.7157 0.039 Uiso 1 1 calc R U . . .
C15 C 0.8543(7) 0.5163(5) 0.5331(10) 0.0195(18) Uani 1 1 d . . . . .
H15A H 0.7792 0.4926 0.4911 0.029 Uiso 1 1 calc R U . . .
H15B H 0.8971 0.4715 0.6145 0.029 Uiso 1 1 calc R U . . .
H15C H 0.8875 0.5223 0.4427 0.029 Uiso 1 1 calc R U . . .
C16 C 0.7773(7) 0.6818(5) 0.4877(10) 0.0200(19) Uani 1 1 d . . . . .
H16A H 0.7066 0.6504 0.4412 0.030 Uiso 1 1 calc R U . . .
H16B H 0.8111 0.6961 0.4001 0.030 Uiso 1 1 calc R U . . .
H16C H 0.7661 0.7413 0.5414 0.030 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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 '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
N1 Ni1 N1 180.0 3_666 . ?
N1 Ni1 N2 101.6(2) 3_666 . ?
N1 Ni1 N2 78.4(2) . . ?
N1 Ni1 N2 78.4(2) 3_666 3_666 ?
N1 Ni1 N2 101.6(2) . 3_666 ?
N2 Ni1 N2 180.0(3) . 3_666 ?
N1 Ni1 Cl1 87.47(18) 3_666 3_666 ?
N1 Ni1 Cl1 92.53(18) . 3_666 ?
N2 Ni1 Cl1 87.14(17) . 3_666 ?
N2 Ni1 Cl1 92.86(17) 3_666 3_666 ?
N1 Ni1 Cl1 92.53(18) 3_666 . ?
N1 Ni1 Cl1 87.47(18) . . ?
N2 Ni1 Cl1 92.86(17) . . ?
N2 Ni1 Cl1 87.14(17) 3_666 . ?
Cl1 Ni1 Cl1 180.0 3_666 . ?
C1 N1 C5 118.0(6) . . ?
C1 N1 Ni1 128.4(5) . . ?
C5 N1 Ni1 113.5(5) . . ?
C6 N2 C7 116.2(6) . . ?
C6 N2 Ni1 110.3(6) . . ?
C7 N2 Ni1 130.4(4) . . ?
N1 C1 C2 122.6(7) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 118.7(8) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 119.4(7) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 119.2(7) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 122.1(8) . . ?
N1 C5 C6 115.7(6) . . ?
C4 C5 C6 122.2(7) . . ?
N2 C6 C5 121.2(7) . . ?
N2 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C12 120.5(7) . . ?
C8 C7 N2 114.1(7) . . ?
C12 C7 N2 125.4(7) . . ?
C9 C8 C7 122.0(8) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C10 C9 C8 118.1(8) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C11 C10 C9 120.5(8) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 123.1(8) . . ?
C10 C11 H11 118.5 . . ?
C12 C11 H11 118.5 . . ?
C7 C12 C11 115.8(7) . . ?
C7 C12 C13 126.0(7) . . ?
C11 C12 C13 118.1(7) . . ?
C16 C13 C12 113.8(7) . . ?
C16 C13 C14 106.5(6) . . ?
C12 C13 C14 111.3(7) . . ?
C16 C13 C15 108.3(7) . . ?
C12 C13 C15 108.0(6) . . ?
C14 C13 C15 108.7(7) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
Ni1 N1 2.099(6) 3_666 ?
Ni1 N1 2.099(6) . ?
Ni1 N2 2.188(6) . ?
Ni1 N2 2.188(6) 3_666 ?
Ni1 Cl1 2.373(2) 3_666 ?
Ni1 Cl1 2.373(2) . ?
N1 C1 1.327(10) . ?
N1 C5 1.355(9) . ?
N2 C6 1.273(9) . ?
N2 C7 1.435(10) . ?
C1 C2 1.405(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.367(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.453(11) . ?
C6 H6 0.9500 . ?
C7 C8 1.400(11) . ?
C7 C12 1.403(11) . ?
C8 C9 1.384(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.374(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.413(11) . ?
C11 H11 0.9500 . ?
C12 C13 1.541(10) . ?
C13 C16 1.539(11) . ?
C13 C14 1.543(11) . ?
C13 C15 1.548(10) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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
C5 N1 C1 C2 -1.9(12) . . . . ?
Ni1 N1 C1 C2 -176.9(6) . . . . ?
N1 C1 C2 C3 0.8(13) . . . . ?
C1 C2 C3 C4 0.0(13) . . . . ?
C2 C3 C4 C5 0.3(13) . . . . ?
C1 N1 C5 C4 2.2(12) . . . . ?
Ni1 N1 C5 C4 178.0(6) . . . . ?
C1 N1 C5 C6 -178.4(7) . . . . ?
Ni1 N1 C5 C6 -2.7(9) . . . . ?
C3 C4 C5 N1 -1.5(13) . . . . ?
C3 C4 C5 C6 179.2(8) . . . . ?
C7 N2 C6 C5 -173.9(7) . . . . ?
Ni1 N2 C6 C5 -11.7(9) . . . . ?
N1 C5 C6 N2 10.4(12) . . . . ?
C4 C5 C6 N2 -170.3(8) . . . . ?
C6 N2 C7 C8 81.4(8) . . . . ?
Ni1 N2 C7 C8 -76.5(8) . . . . ?
C6 N2 C7 C12 -100.2(9) . . . . ?
Ni1 N2 C7 C12 102.0(8) . . . . ?
C12 C7 C8 C9 0.7(11) . . . . ?
N2 C7 C8 C9 179.2(6) . . . . ?
C7 C8 C9 C10 0.9(11) . . . . ?
C8 C9 C10 C11 -1.5(11) . . . . ?
C9 C10 C11 C12 0.6(12) . . . . ?
C8 C7 C12 C11 -1.6(10) . . . . ?
N2 C7 C12 C11 -179.9(6) . . . . ?
C8 C7 C12 C13 175.8(7) . . . . ?
N2 C7 C12 C13 -2.5(11) . . . . ?
C10 C11 C12 C7 1.0(11) . . . . ?
C10 C11 C12 C13 -176.7(7) . . . . ?
C7 C12 C13 C16 35.5(10) . . . . ?
C11 C12 C13 C16 -147.1(7) . . . . ?
C7 C12 C13 C14 155.9(7) . . . . ?
C11 C12 C13 C14 -26.7(9) . . . . ?
C7 C12 C13 C15 -84.8(9) . . . . ?
C11 C12 C13 C15 92.5(8) . . . . ?
