#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:12:13 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266116 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/26/7242639.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_7242639
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         'C20 H18 N4 Ni O2, 2(C H Cl3)'
_chemical_formula_sum            'C22 H20 Cl6 N4 Ni O2'
_chemical_formula_weight         643.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-03-30 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.022(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0319(3)
_cell_length_b                   11.2984(2)
_cell_length_c                   16.0579(3)
_cell_measurement_reflns_used    7500
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      2.217
_cell_volume                     2607.74(9)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11375
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.150
_diffrn_reflns_theta_min         2.238
_exptl_absorpt_coefficient_mu    1.388
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.507
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_description       prism
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.532
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     59
_refine_ls_restrained_S_all      1.917
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0434P)²+7.0737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1064
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2712
_reflns_number_total             2948
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1gc00388g2.cif
_cod_data_source_block           17ma160_sb380
_cod_depositor_comments
'Adding full bibliography for 7242639--7242644.cif.'
_cod_database_code               7242639
_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_max   0.908
_shelx_estimated_absorpt_t_min   0.526
_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. Restrained distances
 Cl7-C1S
 1.75 with sigma of 0.02
 C1S-Cl1 \\sim C1S-Cl2 \\sim C1S-Cl3 \\sim C1S-Cl4 \\sim C1S-Cl5 \\sim C1S-Cl6
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(Cl3) \\sim Ueq, Uanis(Cl4)
\\sim Ueq, Uanis(Cl5) \\sim Ueq, Uanis(Cl6) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
Uanis(Cl7) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.002
4. Others
 1*[Sof(Cl2)]+1*[Sof(Cl5)]+1*[Sof(Cl7)]=1 with esd of 0.0001
 Sof(Cl4)=1-FVAR(1)
 Sof(Cl3)=FVAR(1)
 Sof(Cl6)=1-FVAR(2)
 Sof(Cl1)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8)
5.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
C1 C 0.65114(17) 0.4512(2) 0.84212(14) 0.0299(5) Uani 1 1 d . . . . .
C2 C 0.6053(2) 0.5529(2) 0.80040(16) 0.0393(6) Uani 1 1 d . . . . .
H2 H 0.6230 0.6282 0.8263 0.047 Uiso 1 1 calc R U . . .
C3 C 0.5349(2) 0.5461(2) 0.72265(16) 0.0405(6) Uani 1 1 d . . . . .
H3 H 0.5061 0.6165 0.6953 0.049 Uiso 1 1 calc R U . . .
C4 C 0.50625(18) 0.4377(3) 0.68427(16) 0.0399(6) Uani 1 1 d . . . . .
H4 H 0.4558 0.4332 0.6323 0.048 Uiso 1 1 calc R U . . .
C5 C 0.55138(16) 0.3361(2) 0.72198(15) 0.0315(5) Uani 1 1 d . . . . .
H5 H 0.5327 0.2614 0.6954 0.038 Uiso 1 1 calc R U . . .
C6 C 0.62429(15) 0.34286(19) 0.79905(13) 0.0246(4) Uani 1 1 d . . . . .
C7 C 0.68772(17) 0.1441(2) 0.78010(14) 0.0280(5) Uani 1 1 d . . . . .
H7 H 0.6536 0.1306 0.7210 0.034 Uiso 1 1 calc R U . . .
C8 C 0.75383(17) 0.0746(2) 0.83022(15) 0.0302(5) Uani 1 1 d . . . . .
H8 H 0.7755 0.0020 0.8134 0.036 Uiso 1 1 calc R U . . .
C9 C 0.73810(14) 0.23019(18) 0.91300(13) 0.0221(4) Uani 1 1 d . . . . .
C10 C 0.86104(17) 0.0800(2) 0.98168(16) 0.0359(5) Uani 1 1 d . . . . .
H10A H 0.8924 0.1445 1.0198 0.054 Uiso 1 1 calc R U . . .
H10B H 0.9056 0.0399 0.9573 0.054 Uiso 1 1 calc R U . . .
H10C H 0.8362 0.0232 1.0154 0.054 Uiso 1 1 calc R U . . .
N1 N 0.67846(12) 0.24011(16) 0.83100(11) 0.0225(4) Uani 1 1 d . . . . .
N2 N 0.78490(13) 0.12796(16) 0.91109(12) 0.0254(4) Uani 1 1 d . . . . .
Ni1 Ni 0.7500 0.34071(3) 1.0000 0.02330(13) Uani 1 2 d S T P . .
O1 O 0.71743(14) 0.46194(14) 0.91701(10) 0.0381(4) Uani 1 1 d . . . . .
C1S C 0.3751(3) 0.3551(3) 0.9374(2) 0.0796(14) Uani 1 1 d D . . . .
Cl1 Cl 0.38723(14) 0.37707(18) 0.84061(10) 0.0719(7) Uani 0.635(4) 1 d D U P A
1
Cl2 Cl 0.3253(2) 0.2361(2) 0.9662(3) 0.1107(13) Uani 0.470(3) 1 d D U P A 1
Cl3 Cl 0.50242(18) 0.3445(2) 1.01307(14) 0.0901(10) Uani 0.501(3) 1 d D U P A 1
Cl4 Cl 0.42444(17) 0.26533(19) 1.01216(12) 0.0733(8) Uani 0.499(3) 1 d D U P A
2
Cl5 Cl 0.3035(3) 0.2785(4) 0.8374(2) 0.120(2) Uani 0.364(3) 1 d D U P A 2
Cl6 Cl 0.4432(3) 0.4465(5) 0.8962(4) 0.117(2) Uani 0.365(4) 1 d D U P A 2
Cl7 Cl 0.2735(6) 0.2208(7) 0.8835(7) 0.088(2) Uani 0.166(3) 1 d D U P A 3
H1S H 0.341(3) 0.405(4) 0.953(3) 0.073(12) Uiso 1 1 d . . . . .
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
C2 C1 C6 116.6(2) . . ?
O1 C1 C2 119.5(2) . . ?
O1 C1 C6 123.9(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.6(2) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.1(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 N1 118.75(19) . . ?
C5 C6 C1 121.5(2) . . ?
C5 C6 N1 119.5(2) . . ?
C8 C7 H7 126.6 . . ?
C8 C7 N1 106.83(19) . . ?
N1 C7 H7 126.6 . . ?
C7 C8 H8 126.4 . . ?
C7 C8 N2 107.3(2) . . ?
N2 C8 H8 126.4 . . ?
N1 C9 Ni1 124.53(15) . . ?
N2 C9 N1 104.29(17) . . ?
N2 C9 Ni1 131.13(15) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
C7 N1 C6 124.71(18) . . ?
C9 N1 C6 124.04(18) . . ?
C9 N1 C7 110.68(18) . . ?
C8 N2 C10 122.7(2) . . ?
C9 N2 C8 110.93(18) . . ?
C9 N2 C10 126.33(19) . . ?
C9 Ni1 C9 94.70(12) . 2_657 ?
C9 Ni1 O1 90.51(8) 2_657 2_657 ?
C9 Ni1 O1 169.03(9) 2_657 . ?
C9 Ni1 O1 90.51(8) . . ?
C9 Ni1 O1 169.03(9) . 2_657 ?
O1 Ni1 O1 86.04(10) . 2_657 ?
C1 O1 Ni1 123.36(15) . . ?
Cl1 C1S Cl2 124.7(3) . . ?
Cl1 C1S Cl3 103.8(2) . . ?
Cl1 C1S H1S 115(3) . . ?
Cl2 C1S Cl3 102.5(2) . . ?
Cl2 C1S H1S 95(3) . . ?
Cl3 C1S H1S 115(3) . . ?
Cl4 C1S Cl5 112.4(3) . . ?
Cl4 C1S Cl6 118.6(3) . . ?
Cl4 C1S H1S 113(3) . . ?
Cl5 C1S H1S 108(3) . . ?
Cl6 C1S Cl5 102.0(4) . . ?
Cl6 C1S H1S 101(3) . . ?
Cl7 C1S H1S 99(3) . . ?
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
C1 C2 1.405(3) . ?
C1 C6 1.406(3) . ?
C1 O1 1.324(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(3) . ?
C6 N1 1.425(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.336(3) . ?
C7 N1 1.389(3) . ?
C8 H8 0.9500 . ?
C8 N2 1.383(3) . ?
C9 N1 1.363(3) . ?
C9 N2 1.357(3) . ?
C9 Ni1 1.843(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 N2 1.459(3) . ?
Ni1 C9 1.843(2) 2_657 ?
Ni1 O1 1.8735(16) . ?
Ni1 O1 1.8735(16) 2_657 ?
C1S Cl1 1.636(3) . ?
C1S Cl2 1.669(4) . ?
C1S Cl3 1.948(4) . ?
C1S Cl4 1.581(3) . ?
C1S Cl5 1.863(5) . ?
C1S Cl6 1.717(4) . ?
C1S Cl7 2.147(8) . ?
C1S H1S 0.85(4) . ?
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
C1 C2 C3 C4 1.3(4) . . . . ?
C1 C6 N1 C7 -151.2(2) . . . . ?
C1 C6 N1 C9 19.3(3) . . . . ?
C2 C1 C6 C5 -4.4(3) . . . . ?
C2 C1 C6 N1 169.9(2) . . . . ?
C2 C1 O1 Ni1 154.4(2) . . . . ?
C2 C3 C4 C5 -3.1(4) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C4 C5 C6 C1 2.7(4) . . . . ?
C4 C5 C6 N1 -171.5(2) . . . . ?
C5 C6 N1 C7 23.2(3) . . . . ?
C5 C6 N1 C9 -166.3(2) . . . . ?
C6 C1 C2 C3 2.4(4) . . . . ?
C6 C1 O1 Ni1 -27.3(3) . . . . ?
C7 C8 N2 C9 0.8(3) . . . . ?
C7 C8 N2 C10 -176.7(2) . . . . ?
C8 C7 N1 C6 171.1(2) . . . . ?
C8 C7 N1 C9 -0.5(3) . . . . ?
C9 Ni1 O1 C1 40.4(2) . . . . ?
C9 Ni1 O1 C1 -78.0(5) 2_657 . . . ?
N1 C7 C8 N2 -0.2(3) . . . . ?
N1 C9 N2 C8 -1.1(2) . . . . ?
N1 C9 N2 C10 176.3(2) . . . . ?
N1 C9 Ni1 C9 140.3(2) . . . 2_657 ?
N1 C9 Ni1 O1 -101.6(4) . . . 2_657 ?
N1 C9 Ni1 O1 -30.04(19) . . . . ?
N2 C9 N1 C6 -170.72(19) . . . . ?
N2 C9 N1 C7 0.9(2) . . . . ?
N2 C9 Ni1 C9 -42.98(17) . . . 2_657 ?
N2 C9 Ni1 O1 75.1(5) . . . 2_657 ?
N2 C9 Ni1 O1 146.7(2) . . . . ?
Ni1 C9 N1 C6 6.7(3) . . . . ?
Ni1 C9 N1 C7 178.38(16) . . . . ?
Ni1 C9 N2 C8 -178.26(17) . . . . ?
Ni1 C9 N2 C10 -0.9(3) . . . . ?
O1 C1 C2 C3 -179.3(2) . . . . ?
O1 C1 C6 C5 177.4(2) . . . . ?
O1 C1 C6 N1 -8.4(4) . . . . ?
O1 Ni1 O1 C1 -150.0(2) 2_657 . . . ?
