#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:12:13 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266116 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/26/7242644.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_7242644
loop_
_publ_author_name
'Bertini, Simone'
'Rahaman, Motiar'
'Dutta, Abhijit'
'Schollhammer, Philippe'
'Rudnev, Alexander V.'
'Gloaguen, Fredric'
'Broekmann, Peter'
'Albrecht, Martin'
_publ_section_title
;
 Oxo-functionalised mesoionic NHC nickel complexes for selective
 electrocatalytic reduction of CO2 to formate
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              3365
_journal_page_last               3373
_journal_paper_doi               10.1039/D1GC00388G
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C36 H36 N6 Ni O2'
_chemical_formula_sum            'C36 H36 N6 Ni O2'
_chemical_formula_weight         643.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_audit_update_record
;
2020-05-15 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.6340(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.11310(10)
_cell_length_b                   10.38960(10)
_cell_length_c                   14.69520(10)
_cell_measurement_reflns_used    14089
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.9970
_cell_measurement_theta_min      1.9880
_cell_volume                     1598.07(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0965
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00 109.00   1.00    4.97    --   27.49  38.00 -30.00  137
  2  ω    -54.00  83.00   1.00    4.97    --   27.49 -38.00  30.00  137
  3  ω    -10.00 103.00   1.00    4.97    --   27.49  57.00   0.00  113
  4  ω    -16.00 112.00   1.00    4.97    --   27.49  77.00-180.00  128
  5  ω    -49.00  65.00   1.00    4.97    --   27.49 -57.00-180.00  114
  6  ω    -20.00  28.00   1.00    4.97    --  -23.50 -99.00 -60.00   48
  7  ω    -20.00  83.00   1.00    4.97    --   27.49 -99.00  60.00  103
  8  ω    -54.00  83.00   1.00    4.97    --   27.49 -38.00-120.00  137
  9  ω    -10.00 103.00   1.00    4.97    --   27.49  57.00 120.00  113
 10  ω     35.00 122.00   1.00    4.97    --   27.49 178.00  60.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0256630000
_diffrn_orient_matrix_UB_12      -0.0576975000
_diffrn_orient_matrix_UB_13      -0.0247453000
_diffrn_orient_matrix_UB_21      0.0615510000
_diffrn_orient_matrix_UB_22      -0.0178503000
_diffrn_orient_matrix_UB_23      -0.0001198000
_diffrn_orient_matrix_UB_31      0.0120234000
_diffrn_orient_matrix_UB_32      -0.0318363000
_diffrn_orient_matrix_UB_33      0.0448803000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26452
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.007
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       prism
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0298
_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)+(0.0433P)²+0.5772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3269
_reflns_number_total             3647
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1gc00388g2.cif
_cod_data_source_block           17ma116_SB279
_cod_depositor_comments
'Adding full bibliography for 7242639--7242644.cif.'
_cod_database_code               7242644
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C36H36N6Ni1O2
_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   0.854
_shelx_estimated_absorpt_t_min   0.829
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C16(H16), C10(H10), C12(H12), C18(H18), C11(H11)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C20(H20A,H20B,H20C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.834
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.02092(9) Uani 1 2 d S T P . .
O1 O 0.44240(10) 0.43495(10) 0.59542(7) 0.0296(2) Uani 1 1 d . . . . .
N1 N 0.34444(11) 0.68949(11) 0.55457(8) 0.0238(2) Uani 1 1 d . . . . .
N3 N 0.27533(11) 0.82651(12) 0.44716(9) 0.0268(3) Uani 1 1 d . . . . .
N2 N 0.26777(12) 0.79256(12) 0.53155(9) 0.0288(3) Uani 1 1 d . . . . .
C5 C 0.40031(13) 0.65445(13) 0.48764(10) 0.0224(3) Uani 1 1 d . . . . .
C4 C 0.35308(13) 0.74891(13) 0.41643(10) 0.0237(3) Uani 1 1 d . . . . .
C7 C 0.35922(13) 0.62775(14) 0.64455(10) 0.0243(3) Uani 1 1 d . . . . .
C8 C 0.40545(14) 0.50067(13) 0.65782(11) 0.0236(3) Uani 1 1 d . . . . .
C14 C 0.36928(13) 0.78022(13) 0.32268(10) 0.0234(3) Uani 1 1 d . . . . .
C15 C 0.47446(13) 0.85313(13) 0.32051(10) 0.0252(3) Uani 1 1 d . . . . .
C9 C 0.40778(14) 0.44068(15) 0.74489(11) 0.0291(3) Uani 1 1 d . . . . .
H9 H 0.4339 0.3553 0.7559 0.035 Uiso 1 1 calc R . . . .
C13 C 0.27186(14) 0.74841(14) 0.23616(11) 0.0279(3) Uani 1 1 d . . . . .
C16 C 0.48167(14) 0.89107(14) 0.23169(11) 0.0291(3) Uani 1 1 d . . . . .
H16 H 0.5524 0.9376 0.2301 0.035 Uiso 1 1 calc R . . . .
C10 C 0.37226(16) 0.50552(15) 0.81402(12) 0.0306(3) Uani 1 1 d . . . . .
H10 H 0.3738 0.4630 0.8701 0.037 Uiso 1 1 calc R . . . .
C12 C 0.32666(15) 0.69429(15) 0.71542(11) 0.0306(3) Uani 1 1 d . . . . .
H12 H 0.2998 0.7795 0.7051 0.037 Uiso 1 1 calc R . . . .
C6 C 0.20015(16) 0.93763(15) 0.39773(12) 0.0358(4) Uani 1 1 d . . . . .
H6A H 0.1627 0.9793 0.4401 0.054 Uiso 1 1 calc GR . . . .
H6B H 0.1338 0.9091 0.3405 0.054 Uiso 1 1 calc GR . . . .
H6C H 0.2548 0.9971 0.3803 0.054 Uiso 1 1 calc GR . . . .
C17 C 0.38604(16) 0.86127(15) 0.14535(11) 0.0325(3) Uani 1 1 d . . . . .
C18 C 0.28183(15) 0.79065(15) 0.14922(11) 0.0322(3) Uani 1 1 d . . . . .
H18 H 0.2167 0.7710 0.0919 0.039 Uiso 1 1 calc R . . . .
C20 C 0.57952(15) 0.88851(17) 0.41204(11) 0.0345(3) Uani 1 1 d . . . . .
H20A H 0.5431 0.9168 0.4593 0.052 Uiso 1 1 calc GR . . . .
H20B H 0.6299 0.9566 0.3991 0.052 Uiso 1 1 calc GR . . . .
H20C H 0.6327 0.8148 0.4362 0.052 Uiso 1 1 calc GR . . . .
C11 C 0.33414(15) 0.63413(16) 0.80065(11) 0.0331(3) Uani 1 1 d . . . . .
H11 H 0.3141 0.6786 0.8486 0.040 Uiso 1 1 calc R . . . .
C19 C 0.15845(16) 0.66987(17) 0.23688(13) 0.0393(4) Uani 1 1 d . . . . .
H19A H 0.1872 0.5891 0.2685 0.059 Uiso 1 1 calc GR . . . .
H19B H 0.1039 0.6545 0.1717 0.059 Uiso 1 1 calc GR . . . .
H19C H 0.1119 0.7159 0.2710 0.059 Uiso 1 1 calc GR . . . .
C21 C 0.3953(2) 0.9059(2) 0.05037(13) 0.0522(5) Uani 1 1 d . . . . .
H21A H 0.4158 0.9960 0.0543 0.078 Uiso 1 1 calc GR . . . .
H21B H 0.3150 0.8920 0.0000 0.078 Uiso 1 1 calc GR . . . .
H21C H 0.4609 0.8583 0.0363 0.078 Uiso 1 1 calc GR . . . .
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
_geom_angle_publ_flag
O1 Ni1 O1 180.00(3) . 3_666 ?
O1 Ni1 C5 92.37(5) . . ?
O1 Ni1 C5 87.64(5) 3_666 . ?
O1 Ni1 C5 87.64(5) . 3_666 ?
O1 Ni1 C5 92.36(5) 3_666 3_666 ?
C5 Ni1 C5 180.0 . 3_666 ?
C8 O1 Ni1 127.33(9) . . ?
N2 N1 C5 115.61(11) . . ?
N2 N1 C7 117.28(11) . . ?
C5 N1 C7 127.10(11) . . ?
N2 N3 C4 113.61(11) . . ?
N2 N3 C6 118.07(12) . . ?
C4 N3 C6 128.31(12) . . ?
N3 N2 N1 102.43(11) . . ?
N1 C5 Ni1 122.46(10) . . ?
N1 C5 C4 101.68(11) . . ?
C4 C5 Ni1 135.56(10) . . ?
N3 C4 C5 106.65(12) . . ?
N3 C4 C14 117.74(12) . . ?
C5 C4 C14 135.61(12) . . ?
C8 C7 N1 118.23(12) . . ?
C12 C7 N1 119.37(13) . . ?
C12 C7 C8 122.40(13) . . ?
O1 C8 C7 125.16(13) . . ?
O1 C8 C9 119.11(12) . . ?
C7 C8 C9 115.70(13) . . ?
C15 C14 C4 120.10(13) . . ?
C15 C14 C13 120.10(13) . . ?
C13 C14 C4 119.44(13) . . ?
C14 C15 C20 121.03(13) . . ?
C16 C15 C14 119.05(13) . . ?
C16 C15 C20 119.91(13) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.77(14) . . ?
C10 C9 H9 119.1 . . ?
C14 C13 C19 120.94(14) . . ?
C18 C13 C14 118.84(14) . . ?
C18 C13 C19 120.22(14) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 C15 121.75(14) . . ?
C17 C16 H16 119.1 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.75(14) . . ?
C11 C10 H10 119.6 . . ?
C7 C12 H12 119.9 . . ?
C11 C12 C7 120.16(14) . . ?
C11 C12 H12 119.9 . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C16 C17 C21 120.55(15) . . ?
C18 C17 C16 118.24(13) . . ?
C18 C17 C21 121.20(15) . . ?
C13 C18 H18 119.0 . . ?
C17 C18 C13 121.99(14) . . ?
C17 C18 H18 119.0 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.03(14) . . ?
C12 C11 H11 120.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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 O1 1.8536(10) . ?
Ni1 O1 1.8537(10) 3_666 ?
Ni1 C5 1.9236(13) . ?
Ni1 C5 1.9236(13) 3_666 ?
O1 C8 1.3148(17) . ?
N1 N2 1.3393(16) . ?
N1 C5 1.3769(17) . ?
N1 C7 1.4285(17) . ?
N3 N2 1.3188(17) . ?
N3 C4 1.3647(18) . ?
N3 C6 1.4665(18) . ?
C5 C4 1.4016(19) . ?
C4 C14 1.4844(19) . ?
C7 C8 1.4064(19) . ?
C7 C12 1.3953(19) . ?
C8 C9 1.416(2) . ?
C14 C15 1.402(2) . ?
C14 C13 1.405(2) . ?
C15 C16 1.391(2) . ?
C15 C20 1.501(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(2) . ?
C13 C18 1.390(2) . ?
C13 C19 1.504(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.396(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.377(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C17 C18 1.388(2) . ?
C17 C21 1.507(2) . ?
C18 H18 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C11 H11 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
