#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:56:14 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289500 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/47/7714735.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_7714735
loop_
_publ_author_name
'Sanz-Garrido, Jorge'
'Martin, Avelino'
'González-Arellano, Camino'
'Flores, Juan C.'
_publ_section_title
;
 Half-sandwich Ni(II) complexes bearing enantiopure bidentate
 NHC-carboxylate ligands: efficient catalysts for the hydrosilylative
 reduction of acetophenones.
;
_journal_issue                   4
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1460
_journal_page_last               1468
_journal_paper_doi               10.1039/d3dt03739h
_journal_volume                  53
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C34 H42 N4 Ni O4, 2(C H Cl3)'
_chemical_formula_sum            'C36 H44 Cl6 N4 Ni O4'
_chemical_formula_weight         868.16
_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_date             2023-09-25
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-10-23 deposited with the CCDC.	2023-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.0760(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.7822(4)
_cell_length_b                   17.9182(5)
_cell_length_c                   11.2267(4)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    200.00
_cell_measurement_theta_max      27.453
_cell_measurement_theta_min      2.303
_cell_volume                     2073.35(12)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'Apex3 v2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement
;
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
;
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200.00
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type
;
Bruker AXS D8 Venture diffractometer with PhotonIII_C14 charge-integrating and 
photon counting pixel array detector
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            56426
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         1.976
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.0
_diffrn_source_type              'INCOATEC I\ms 3.0'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.896
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0998 before and 0.0662 after correction.
The Ratio of minimum to maximum transmission is 0.8993.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.033(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         9405
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0338
_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)+(0.0294P)²+0.5602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0697
_reflns_Friedel_coverage         0.936
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                8896
_reflns_number_total             9405
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt03739h2.cif
_cod_data_source_block           pgsval2ni_0m_a
_cod_depositor_comments
'Adding full bibliography for 7714726--7714736.cif.'
_cod_database_code               7714735
_shelx_shelxl_version_number     2018/3
_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_max   0.951
_shelx_estimated_absorpt_t_min   0.820
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.967(11)
 0.033(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C25(H25), C26(H26), C42(H42), C41(H41)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C11(H11), C13(H13), C22(H22), C23(H23), C31(H31), C33(H33)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C),
 C17(H17A,H17B,H17C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C35(H35A,H35B,
 H35C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.25190(4) 0.50816(2) 0.49050(3) 0.01939(8) Uani 1 1 d . . . . .
O1 O 0.3400(2) 0.41676(11) 0.52197(19) 0.0256(4) Uani 1 1 d . . . . .
O2 O 0.3579(3) 0.30000(12) 0.5876(2) 0.0397(6) Uani 1 1 d . . . . .
O21 O 0.1629(2) 0.59825(11) 0.45564(19) 0.0270(4) Uani 1 1 d . . . . .
O22 O 0.1355(3) 0.71672(12) 0.4007(2) 0.0407(6) Uani 1 1 d . . . . .
N1 N -0.0218(2) 0.45108(13) 0.3771(2) 0.0257(5) Uani 1 1 d . . . . .
N2 N 0.0891(2) 0.39770(13) 0.5444(2) 0.0234(5) Uani 1 1 d . . . . .
N21 N 0.5300(2) 0.54953(13) 0.6058(2) 0.0243(5) Uani 1 1 d . . . . .
N22 N 0.4254(2) 0.62204(12) 0.4594(2) 0.0225(5) Uani 1 1 d . . . . .
C1 C 0.0940(3) 0.45368(15) 0.4655(3) 0.0228(6) Uani 1 1 d . . . . .
C2 C -0.0962(3) 0.39267(17) 0.4003(3) 0.0304(6) Uani 1 1 d . . . . .
H2 H -0.181031 0.379323 0.351042 0.037 Uiso 1 1 calc R U . . .
C3 C -0.0267(3) 0.35871(17) 0.5043(3) 0.0299(7) Uani 1 1 d . . . . .
H3 H -0.051582 0.316428 0.542931 0.036 Uiso 1 1 calc R U . . .
C4 C 0.3105(3) 0.36256(16) 0.5834(3) 0.0251(6) Uani 1 1 d . . . . .
C5 C 0.2068(3) 0.38005(15) 0.6492(3) 0.0252(6) Uani 1 1 d . . . . .
H5 H 0.233895 0.427034 0.698012 0.030 Uiso 1 1 calc R U . . .
C6 C 0.1829(3) 0.32157(18) 0.7383(3) 0.0342(7) Uani 1 1 d . . . . .
H6 H 0.150231 0.274666 0.691338 0.041 Uiso 1 1 calc R U . . .
C7 C 0.3111(4) 0.3055(2) 0.8394(4) 0.0515(10) Uani 1 1 d . . . . .
H7A H 0.372510 0.282386 0.801230 0.077 Uiso 1 1 calc R U . . .
H7B H 0.294875 0.271453 0.901545 0.077 Uiso 1 1 calc R U . . .
H7C H 0.347540 0.352297 0.879886 0.077 Uiso 1 1 calc R U . . .
C8 C 0.0835(4) 0.3496(2) 0.8019(4) 0.0508(10) Uani 1 1 d . . . . .
H8A H 0.117726 0.393931 0.851789 0.076 Uiso 1 1 calc R U . . .
H8B H 0.067065 0.310322 0.856203 0.076 Uiso 1 1 calc R U . . .
H8C H 0.002343 0.362257 0.738360 0.076 Uiso 1 1 calc R U . . .
C9 C -0.0609(3) 0.49585(15) 0.2653(3) 0.0259(6) Uani 1 1 d . . . . .
C10 C -0.1448(3) 0.55496(18) 0.2603(3) 0.0323(7) Uani 1 1 d . . . . .
C11 C -0.1851(3) 0.5953(2) 0.1499(3) 0.0408(8) Uani 1 1 d . . . . .
H11 H -0.242319 0.636336 0.144442 0.049 Uiso 1 1 calc R U . . .
C12 C -0.1440(4) 0.5773(2) 0.0477(3) 0.0421(8) Uani 1 1 d . . . . .
C13 C -0.0612(3) 0.5172(2) 0.0566(3) 0.0427(8) Uani 1 1 d . . . . .
H13 H -0.033313 0.504295 -0.013487 0.051 Uiso 1 1 calc R U . . .
C14 C -0.0175(3) 0.47514(19) 0.1648(3) 0.0350(7) Uani 1 1 d . . . . .
C15 C -0.1914(4) 0.5755(2) 0.3690(4) 0.0523(10) Uani 1 1 d . . . . .
H15A H -0.258532 0.540195 0.375423 0.078 Uiso 1 1 calc R U . . .
H15B H -0.227628 0.626076 0.357175 0.078 Uiso 1 1 calc R U . . .
H15C H -0.118578 0.573756 0.445578 0.078 Uiso 1 1 calc R U . . .
C16 C -0.1861(5) 0.6228(3) -0.0696(4) 0.0663(13) Uani 1 1 d . . . . .
H16A H -0.272810 0.643233 -0.079292 0.099 Uiso 1 1 calc R U . . .
H16B H -0.188310 0.591060 -0.141295 0.099 Uiso 1 1 calc R U . . .
H16C H -0.124651 0.663783 -0.064758 0.099 Uiso 1 1 calc R U . . .
C17 C 0.0718(5) 0.4098(2) 0.1729(4) 0.0556(11) Uani 1 1 d . . . . .
H17A H 0.158884 0.422874 0.225605 0.083 Uiso 1 1 calc R U . . .
H17B H 0.075610 0.396833 0.089216 0.083 Uiso 1 1 calc R U . . .
H17C H 0.039215 0.367000 0.209091 0.083 Uiso 1 1 calc R U . . .
C21 C 0.4112(3) 0.56020(15) 0.5228(3) 0.0210(5) Uani 1 1 d . . . . .
C22 C 0.6165(3) 0.60380(17) 0.5918(3) 0.0303(6) Uani 1 1 d . . . . .
H22 H 0.705312 0.607936 0.638335 0.036 Uiso 1 1 calc R U . . .
C23 C 0.5508(3) 0.64929(16) 0.5000(3) 0.0284(6) Uani 1 1 d . . . . .
H23 H 0.583912 0.691837 0.469018 0.034 Uiso 1 1 calc R U . . .
C24 C 0.1970(3) 0.65862(15) 0.4107(3) 0.0249(6) Uani 1 1 d . . . . .
C25 C 0.3177(3) 0.65685(15) 0.3648(3) 0.0251(6) Uani 1 1 d . . . . .
H25 H 0.342782 0.709748 0.355358 0.030 Uiso 1 1 calc R U . . .
C26 C 0.2916(3) 0.61916(17) 0.2371(3) 0.0322(7) Uani 1 1 d . . . . .
H26 H 0.265739 0.566245 0.245233 0.039 Uiso 1 1 calc R U . . .
C27 C 0.1782(4) 0.6585(2) 0.1423(3) 0.0499(9) Uani 1 1 d . . . . .
H27A H 0.100514 0.655502 0.170396 0.075 Uiso 1 1 calc R U . . .
H27B H 0.161330 0.634016 0.060952 0.075 Uiso 1 1 calc R U . . .
H27C H 0.200536 0.710934 0.134882 0.075 Uiso 1 1 calc R U . . .
C28 C 0.4126(4) 0.6186(2) 0.1930(3) 0.0498(10) Uani 1 1 d . . . . .
H28A H 0.440857 0.670044 0.186272 0.075 Uiso 1 1 calc R U . . .
H28B H 0.392722 0.594349 0.111285 0.075 Uiso 1 1 calc R U . . .
H28C H 0.482058 0.591146 0.252956 0.075 Uiso 1 1 calc R U . . .
C29 C 0.5612(3) 0.49808(16) 0.7091(3) 0.0260(6) Uani 1 1 d . . . . .
C30 C 0.6454(3) 0.43918(17) 0.7097(3) 0.0301(6) Uani 1 1 d . . . . .
C31 C 0.6803(3) 0.39356(19) 0.8150(3) 0.0383(8) Uani 1 1 d . . . . .
H31 H 0.737885 0.353088 0.817422 0.046 Uiso 1 1 calc R U . . .
C32 C 0.6342(4) 0.4051(2) 0.9153(3) 0.0410(8) Uani 1 1 d . . . . .
C33 C 0.5505(4) 0.4645(2) 0.9113(3) 0.0406(8) Uani 1 1 d . . . . .
H33 H 0.517869 0.472690 0.980179 0.049 Uiso 1 1 calc R U . . .
C34 C 0.5129(3) 0.5125(2) 0.8091(3) 0.0330(6) Uani 1 1 d . . . . .
C35 C 0.7001(4) 0.4259(2) 0.6033(4) 0.0459(9) Uani 1 1 d . . . . .
H35A H 0.633708 0.436885 0.524544 0.069 Uiso 1 1 calc R U . . .
H35B H 0.726916 0.373592 0.603673 0.069 Uiso 1 1 calc R U . . .
H35C H 0.775250 0.458401 0.611945 0.069 Uiso 1 1 calc R U . . .
C36 C 0.6744(5) 0.3548(3) 1.0281(4) 0.0642(12) Uani 1 1 d . . . . .
H36A H 0.611962 0.313855 1.018174 0.096 Uiso 1 1 calc R U . . .
H36B H 0.676456 0.383594 1.102883 0.096 Uiso 1 1 calc R U . . .
H36C H 0.760836 0.334392 1.036392 0.096 Uiso 1 1 calc R U . . .
C37 C 0.4250(4) 0.5773(2) 0.8095(3) 0.0492(10) Uani 1 1 d . . . . .
H37A H 0.465945 0.623466 0.792986 0.074 Uiso 1 1 calc R U . . .
H37B H 0.409493 0.580792 0.891060 0.074 Uiso 1 1 calc R U . . .
H37C H 0.342296 0.570101 0.744741 0.074 Uiso 1 1 calc R U . . .
Cl4 Cl 0.47187(13) 0.42404(5) 0.26080(11) 0.0606(3) Uani 1 1 d . . . . .
Cl5 Cl 0.33143(12) 0.28479(6) 0.21761(12) 0.0663(3) Uani 1 1 d . . . . .
Cl6 Cl 0.60120(10) 0.28591(5) 0.35459(11) 0.0538(3) Uani 1 1 d . . . . .
C42 C 0.4551(4) 0.33555(19) 0.3221(3) 0.0375(7) Uani 1 1 d . . . . .
H42 H 0.432037 0.342322 0.401399 0.045 Uiso 1 1 calc R U . . .
Cl1 Cl 0.02596(11) 0.56991(5) 0.71333(11) 0.0567(3) Uani 1 1 d . . . . .
Cl2 Cl -0.10138(10) 0.71095(5) 0.63167(12) 0.0543(3) Uani 1 1 d . . . . .
Cl3 Cl 0.16575(12) 0.70814(6) 0.77864(12) 0.0630(3) Uani 1 1 d . . . . .
C41 C 0.0452(3) 0.66164(19) 0.6646(3) 0.0371(7) Uani 1 1 d . . . . .
H41 H 0.072388 0.658955 0.586825 0.044 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'
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
_geom_angle_publ_flag
O1 Ni1 C1 87.81(10) . . ?
O1 Ni1 C21 90.76(10) . . ?
O21 Ni1 O1 178.75(10) . . ?
O21 Ni1 C1 91.73(11) . . ?
O21 Ni1 C21 89.75(11) . . ?
C21 Ni1 C1 177.32(13) . . ?
C4 O1 Ni1 124.76(19) . . ?
C24 O21 Ni1 128.37(19) . . ?
C1 N1 C2 110.5(2) . . ?
C1 N1 C9 126.3(2) . . ?
C2 N1 C9 122.9(3) . . ?
C1 N2 C3 111.5(3) . . ?
C1 N2 C5 119.2(2) . . ?
C3 N2 C5 128.9(2) . . ?
C21 N21 C22 110.7(2) . . ?
C21 N21 C29 126.3(2) . . ?
C22 N21 C29 122.2(3) . . ?
C21 N22 C23 111.5(2) . . ?
C21 N22 C25 122.9(2) . . ?
C23 N22 C25 125.4(2) . . ?
N1 C1 Ni1 135.9(2) . . ?
N1 C1 N2 104.6(2) . . ?
N2 C1 Ni1 119.2(2) . . ?
N1 C2 H2 126.3 . . ?
C3 C2 N1 107.5(3) . . ?
C3 C2 H2 126.3 . . ?
N2 C3 H3 127.0 . . ?
C2 C3 N2 106.0(3) . . ?
C2 C3 H3 127.0 . . ?
O1 C4 C5 115.6(2) . . ?
O2 C4 O1 123.0(3) . . ?
O2 C4 C5 121.3(3) . . ?
N2 C5 C4 103.5(2) . . ?
N2 C5 H5 107.3 . . ?
N2 C5 C6 113.3(2) . . ?
C4 C5 H5 107.3 . . ?
C6 C5 C4 117.5(2) . . ?
C6 C5 H5 107.3 . . ?
C5 C6 H6 109.5 . . ?
C5 C6 C7 109.0(3) . . ?
C5 C6 C8 110.9(3) . . ?
C7 C6 H6 109.5 . . ?
C7 C6 C8 108.5(3) . . ?
C8 C6 H6 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N1 118.8(3) . . ?
C10 C9 C14 122.9(3) . . ?
C14 C9 N1 118.3(3) . . ?
C9 C10 C11 117.6(3) . . ?
C9 C10 C15 121.9(3) . . ?
C11 C10 C15 120.5(3) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.7(3) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C16 120.8(4) . . ?
C13 C12 C11 118.6(3) . . ?
C13 C12 C16 120.6(4) . . ?
C12 C13 H13 118.9 . . ?
C12 C13 C14 122.1(3) . . ?
C14 C13 H13 118.9 . . ?
C9 C14 C17 121.4(3) . . ?
C13 C14 C9 117.1(3) . . ?
C13 C14 C17 121.5(3) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N21 C21 Ni1 133.0(2) . . ?
N22 C21 Ni1 122.7(2) . . ?
N22 C21 N21 104.3(2) . . ?
N21 C22 H22 126.5 . . ?
C23 C22 N21 107.0(3) . . ?
C23 C22 H22 126.5 . . ?
N22 C23 H23 126.8 . . ?
C22 C23 N22 106.5(3) . . ?
C22 C23 H23 126.8 . . ?
O21 C24 C25 118.7(2) . . ?
O22 C24 O21 122.7(3) . . ?
O22 C24 C25 118.6(3) . . ?
N22 C25 C24 109.7(2) . . ?
N22 C25 H25 107.4 . . ?
N22 C25 C26 112.3(2) . . ?
C24 C25 H25 107.4 . . ?
C24 C25 C26 112.5(2) . . ?
C26 C25 H25 107.4 . . ?
C25 C26 H26 108.2 . . ?
C25 C26 C27 109.6(3) . . ?
C27 C26 H26 108.2 . . ?
C28 C26 C25 111.5(3) . . ?
C28 C26 H26 108.2 . . ?
C28 C26 C27 111.1(3) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 N21 119.1(3) . . ?
C30 C29 C34 122.4(3) . . ?
C34 C29 N21 118.4(3) . . ?
C29 C30 C31 117.5(3) . . ?
C29 C30 C35 121.8(3) . . ?
C31 C30 C35 120.8(3) . . ?
C30 C31 H31 118.9 . . ?
C32 C31 C30 122.3(3) . . ?
C32 C31 H31 118.9 . . ?
C31 C32 C33 118.6(3) . . ?
C31 C32 C36 120.9(4) . . ?
C33 C32 C36 120.5(4) . . ?
C32 C33 H33 119.1 . . ?
C32 C33 C34 121.9(3) . . ?
C34 C33 H33 119.1 . . ?
C29 C34 C33 117.4(3) . . ?
C29 C34 C37 122.1(3) . . ?
C33 C34 C37 120.4(3) . . ?
C30 C35 H35A 109.5 . . ?
C30 C35 H35B 109.5 . . ?
C30 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C32 C36 H36A 109.5 . . ?
C32 C36 H36B 109.5 . . ?
C32 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
Cl4 C42 H42 108.7 . . ?
Cl5 C42 Cl4 110.6(2) . . ?
Cl5 C42 Cl6 109.72(19) . . ?
Cl5 C42 H42 108.7 . . ?
Cl6 C42 Cl4 110.5(2) . . ?
Cl6 C42 H42 108.7 . . ?
Cl1 C41 H41 108.5 . . ?
Cl2 C41 Cl1 110.74(19) . . ?
Cl2 C41 H41 108.5 . . ?
Cl3 C41 Cl1 110.3(2) . . ?
Cl3 C41 Cl2 110.18(19) . . ?
Cl3 C41 H41 108.5 . . ?
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 O1 1.874(2) . ?
Ni1 O21 1.860(2) . ?
Ni1 C1 1.911(3) . ?
Ni1 C21 1.893(3) . ?
O1 C4 1.284(4) . ?
O2 C4 1.227(4) . ?
O21 C24 1.292(3) . ?
O22 C24 1.222(4) . ?
N1 C1 1.348(4) . ?
N1 C2 1.389(4) . ?
N1 C9 1.445(4) . ?
N2 C1 1.349(4) . ?
N2 C3 1.386(4) . ?
N2 C5 1.490(4) . ?
N21 C21 1.358(4) . ?
N21 C22 1.388(4) . ?
N21 C29 1.442(4) . ?
N22 C21 1.350(3) . ?
N22 C23 1.383(4) . ?
N22 C25 1.463(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.335(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.542(4) . ?
C5 H5 1.0000 . ?
C5 C6 1.522(4) . ?
C6 H6 1.0000 . ?
C6 C7 1.536(5) . ?
C6 C8 1.536(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.383(4) . ?
C9 C14 1.393(4) . ?
C10 C11 1.390(5) . ?
C10 C15 1.495(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(5) . ?
C12 C13 1.383(5) . ?
C12 C16 1.502(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(5) . ?
C14 C17 1.502(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C22 H22 0.9500 . ?
C22 C23 1.341(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.534(4) . ?
C25 H25 1.0000 . ?
C25 C26 1.534(4) . ?
C26 H26 1.0000 . ?
C26 C27 1.536(5) . ?
C26 C28 1.526(5) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.391(4) . ?
C29 C34 1.393(4) . ?
C30 C31 1.395(4) . ?
C30 C35 1.498(5) . ?
C31 H31 0.9500 . ?
C31 C32 1.373(5) . ?
C32 C33 1.387(5) . ?
C32 C36 1.511(5) . ?
C33 H33 0.9500 . ?
C33 C34 1.396(5) . ?
C34 C37 1.500(5) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
Cl4 C42 1.759(4) . ?
Cl5 C42 1.750(4) . ?
Cl6 C42 1.751(4) . ?
C42 H42 1.0000 . ?
Cl1 C41 1.764(4) . ?
Cl2 C41 1.753(4) . ?
Cl3 C41 1.745(4) . ?
C41 H41 1.0000 . ?
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
Ni1 O1 C4 O2 169.4(2) . . . . ?
Ni1 O1 C4 C5 -8.6(4) . . . . ?
Ni1 O21 C24 O22 -174.0(2) . . . . ?
Ni1 O21 C24 C25 7.6(4) . . . . ?
O1 Ni1 C21 N21 -36.9(3) . . . . ?
O1 Ni1 C21 N22 143.9(2) . . . . ?
O1 C4 C5 N2 63.0(3) . . . . ?
O1 C4 C5 C6 -171.2(3) . . . . ?
O2 C4 C5 N2 -115.0(3) . . . . ?
O2 C4 C5 C6 10.7(4) . . . . ?
O21 Ni1 C21 N21 144.3(3) . . . . ?
O21 Ni1 C21 N22 -35.0(2) . . . . ?
O21 C24 C25 N22 -48.6(3) . . . . ?
O21 C24 C25 C26 77.0(3) . . . . ?
O22 C24 C25 N22 132.9(3) . . . . ?
O22 C24 C25 C26 -101.5(3) . . . . ?
N1 C2 C3 N2 0.8(3) . . . . ?
N1 C9 C10 C11 -177.5(3) . . . . ?
N1 C9 C10 C15 2.6(5) . . . . ?
N1 C9 C14 C13 177.2(3) . . . . ?
N1 C9 C14 C17 -2.3(5) . . . . ?
N2 C5 C6 C7 177.9(3) . . . . ?
N2 C5 C6 C8 -62.8(3) . . . . ?
N21 C22 C23 N22 -0.1(3) . . . . ?
N21 C29 C30 C31 175.8(3) . . . . ?
N21 C29 C30 C35 -2.7(5) . . . . ?
N21 C29 C34 C33 -176.3(3) . . . . ?
N21 C29 C34 C37 2.9(5) . . . . ?
N22 C25 C26 C27 -179.7(3) . . . . ?
N22 C25 C26 C28 -56.2(3) . . . . ?
C1 Ni1 O1 C4 -39.2(2) . . . . ?
C1 Ni1 O21 C24 -152.5(3) . . . . ?
C1 N1 C2 C3 0.3(4) . . . . ?
C1 N1 C9 C10 -104.1(4) . . . . ?
C1 N1 C9 C14 79.1(4) . . . . ?
C1 N2 C3 C2 -1.7(3) . . . . ?
C1 N2 C5 C4 -57.9(3) . . . . ?
C1 N2 C5 C6 173.7(3) . . . . ?
C2 N1 C1 Ni1 172.0(2) . . . . ?
C2 N1 C1 N2 -1.3(3) . . . . ?
C2 N1 C9 C10 83.5(4) . . . . ?
C2 N1 C9 C14 -93.3(4) . . . . ?
C3 N2 C1 Ni1 -172.8(2) . . . . ?
C3 N2 C1 N1 1.9(3) . . . . ?
C3 N2 C5 C4 113.8(3) . . . . ?
C3 N2 C5 C6 -14.6(4) . . . . ?
C4 C5 C6 C7 57.1(4) . . . . ?
C4 C5 C6 C8 176.5(3) . . . . ?
C5 N2 C1 Ni1 0.2(3) . . . . ?
C5 N2 C1 N1 174.9(2) . . . . ?
C5 N2 C3 C2 -173.9(3) . . . . ?
C9 N1 C1 Ni1 -1.3(5) . . . . ?
C9 N1 C1 N2 -174.6(3) . . . . ?
C9 N1 C2 C3 173.8(3) . . . . ?
C9 C10 C11 C12 0.4(5) . . . . ?
C10 C9 C14 C13 0.6(5) . . . . ?
C10 C9 C14 C17 -178.9(3) . . . . ?
C10 C11 C12 C13 0.3(6) . . . . ?
C10 C11 C12 C16 -178.5(4) . . . . ?
C11 C12 C13 C14 -0.6(6) . . . . ?
C12 C13 C14 C9 0.1(6) . . . . ?
C12 C13 C14 C17 179.6(4) . . . . ?
C14 C9 C10 C11 -0.8(5) . . . . ?
C14 C9 C10 C15 179.2(3) . . . . ?
C15 C10 C11 C12 -179.7(4) . . . . ?
C16 C12 C13 C14 178.2(4) . . . . ?
C21 Ni1 O1 C4 138.6(2) . . . . ?
C21 Ni1 O21 C24 29.7(3) . . . . ?
C21 N21 C22 C23 0.6(3) . . . . ?
C21 N21 C29 C30 115.7(3) . . . . ?
C21 N21 C29 C34 -68.9(4) . . . . ?
C21 N22 C23 C22 -0.5(3) . . . . ?
C21 N22 C25 C24 42.6(3) . . . . ?
C21 N22 C25 C26 -83.2(3) . . . . ?
C22 N21 C21 Ni1 179.8(2) . . . . ?
C22 N21 C21 N22 -0.9(3) . . . . ?
C22 N21 C29 C30 -75.3(4) . . . . ?
C22 N21 C29 C34 100.1(4) . . . . ?
C23 N22 C21 Ni1 -179.7(2) . . . . ?
C23 N22 C21 N21 0.9(3) . . . . ?
C23 N22 C25 C24 -133.7(3) . . . . ?
C23 N22 C25 C26 100.5(3) . . . . ?
C24 C25 C26 C27 56.0(3) . . . . ?
C24 C25 C26 C28 179.5(3) . . . . ?
C25 N22 C21 Ni1 3.5(4) . . . . ?
C25 N22 C21 N21 -175.9(2) . . . . ?
C25 N22 C23 C22 176.2(3) . . . . ?
C29 N21 C21 Ni1 -10.2(4) . . . . ?
C29 N21 C21 N22 169.2(3) . . . . ?
C29 N21 C22 C23 -169.9(3) . . . . ?
C29 C30 C31 C32 0.2(5) . . . . ?
C30 C29 C34 C33 -1.0(5) . . . . ?
C30 C29 C34 C37 178.2(3) . . . . ?
C30 C31 C32 C33 -0.2(5) . . . . ?
C30 C31 C32 C36 -179.7(4) . . . . ?
C31 C32 C33 C34 -0.3(6) . . . . ?
C32 C33 C34 C29 0.9(5) . . . . ?
C32 C33 C34 C37 -178.3(4) . . . . ?
C34 C29 C30 C31 0.5(5) . . . . ?
C34 C29 C30 C35 -178.0(3) . . . . ?
C35 C30 C31 C32 178.6(4) . . . . ?
C36 C32 C33 C34 179.2(4) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.967(11)
2 0.033(11)
