#------------------------------------------------------------------------------
#$Date: 2025-01-06 14:27:44 +0200 (Mon, 06 Jan 2025) $
#$Revision: 297115 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/75/7717512.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_7717512
loop_
_publ_author_name
'Si, Si'
'Song, Wenxun'
'Chen, Jie'
'Zhang, Weimin'
'Ji, Wenhua'
'Nam, Wonwoo'
'Wang, Bin'
_publ_section_title
;
 Neutral nickel complexes with tetradentate N-heterocyclic carbene amidate
 ligands for electrocatalytic hydrogen evolution.
;
_journal_issue                   48
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              19088
_journal_page_last               19092
_journal_paper_doi               10.1039/d4dt02746a
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C18 H16 Cl2 N6 Ni O2, 2(C3 H7 N O)'
_chemical_formula_sum            'C24 H30 Cl2 N8 Ni O4'
_chemical_formula_weight         624.17
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-10-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-06-28 deposited with the CCDC.	2024-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.317(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0789(4)
_cell_length_b                   10.4388(3)
_cell_length_c                   17.9250(5)
_cell_measurement_reflns_used    5969
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.4190
_cell_measurement_theta_min      3.7930
_cell_volume                     2784.27(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0355
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00  33.00   1.00   13.64    --   16.17 -57.00   0.00   84
  2  ω    -25.00  22.00   1.00   13.64    --  -16.64 -99.00 150.00   47
  3  ω    -84.00  10.00   1.00   13.64    --  -16.64 -77.00 -90.00   94
  4  ω    -13.00  33.00   1.00   13.64    --   16.17  19.00 120.00   46
  5  ω    -73.00 -22.00   1.00   13.64    --  -16.64 130.00 130.27   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0214375000
_diffrn_orient_matrix_UB_12      0.0264511000
_diffrn_orient_matrix_UB_13      -0.0288766000
_diffrn_orient_matrix_UB_21      0.0011256000
_diffrn_orient_matrix_UB_22      -0.0614861000
_diffrn_orient_matrix_UB_23      -0.0166907000
_diffrn_orient_matrix_UB_31      -0.0425361000
_diffrn_orient_matrix_UB_32      0.0117328000
_diffrn_orient_matrix_UB_33      -0.0222926000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18576
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.133
_diffrn_reflns_theta_min         3.157
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.935
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       prism
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         6494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0387P)²+1.0247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0939
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4973
_reflns_number_total             6494
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02746a2.cif
_cod_data_source_block           20211023_wb1b
_cod_depositor_comments
'Adding full bibliography for 7717511--7717512.cif.'
_cod_database_code               7717512
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_usercomment     'Ni C H N O Cl'
_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.
;
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C11(H11), C16(H16), C17(H17), C21(H21), C24(H24)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_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 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.914
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 0.39464(2) 0.53996(3) 0.68452(2) 0.02886(9) Uani 1 1 d . . . . .
Cl1 Cl 0.74431(4) 0.67618(9) 0.50461(4) 0.0697(2) Uani 1 1 d . . . . .
Cl2 Cl 0.57378(5) 0.75584(6) 0.38608(4) 0.05376(17) Uani 1 1 d . . . . .
O1 O 0.65912(12) 0.4453(2) 0.71719(13) 0.0770(7) Uani 1 1 d . . . . .
O2 O 0.31495(11) 0.78437(18) 0.51437(10) 0.0554(5) Uani 1 1 d . . . . .
N1 N 0.36106(12) 0.55093(18) 0.84052(10) 0.0387(4) Uani 1 1 d . . . . .
N2 N 0.48037(12) 0.44963(17) 0.82685(10) 0.0372(4) Uani 1 1 d . . . . .
N3 N 0.52085(11) 0.54182(16) 0.68285(9) 0.0316(4) Uani 1 1 d . . . . .
N4 N 0.38193(10) 0.61733(16) 0.58717(9) 0.0285(4) Uani 1 1 d . . . . .
N5 N 0.20963(11) 0.56619(18) 0.62854(10) 0.0370(4) Uani 1 1 d . . . . .
N6 N 0.22967(12) 0.39754(19) 0.69668(10) 0.0392(4) Uani 1 1 d . . . . .
C1 C 0.28346(17) 0.6360(3) 0.82778(14) 0.0510(6) Uani 1 1 d . . . . .
H1A H 0.2959 0.7069 0.7970 0.077 Uiso 1 1 calc GR . . . .
H1B H 0.2712 0.6673 0.8754 0.077 Uiso 1 1 calc GR . . . .
H1C H 0.2322 0.5899 0.8026 0.077 Uiso 1 1 calc GR . . . .
C2 C 0.39998(17) 0.5086(2) 0.91127(12) 0.0461(6) Uani 1 1 d . . . . .
H2 H 0.3784 0.5219 0.9564 0.055 Uiso 1 1 calc R . . . .
C3 C 0.47412(18) 0.4455(2) 0.90257(12) 0.0452(6) Uani 1 1 d . . . . .
H3 H 0.5142 0.4059 0.9405 0.054 Uiso 1 1 calc R . . . .
C4 C 0.41024(14) 0.5128(2) 0.78769(12) 0.0334(5) Uani 1 1 d . . . . .
C5 C 0.55365(16) 0.3963(3) 0.79292(13) 0.0464(6) Uani 1 1 d . . . . .
H5A H 0.5369 0.3101 0.7760 0.056 Uiso 1 1 calc R . . . .
H5B H 0.6059 0.3892 0.8322 0.056 Uiso 1 1 calc R . . . .
C6 C 0.58168(15) 0.4685(2) 0.72676(14) 0.0428(5) Uani 1 1 d . . . . .
C7 C 0.54115(13) 0.5935(2) 0.61447(11) 0.0312(4) Uani 1 1 d . . . . .
C8 C 0.62625(14) 0.6088(2) 0.59492(13) 0.0382(5) Uani 1 1 d . . . . .
H8 H 0.6768 0.5853 0.6291 0.046 Uiso 1 1 calc R . . . .
C9 C 0.63631(14) 0.6580(2) 0.52569(14) 0.0409(5) Uani 1 1 d . . . . .
C10 C 0.56224(15) 0.6907(2) 0.47327(12) 0.0364(5) Uani 1 1 d . . . . .
C11 C 0.47738(14) 0.6758(2) 0.49107(12) 0.0328(4) Uani 1 1 d . . . . .
H11 H 0.4274 0.6957 0.4554 0.039 Uiso 1 1 calc R . . . .
C12 C 0.46575(12) 0.63127(19) 0.56189(11) 0.0283(4) Uani 1 1 d . . . . .
C13 C 0.31419(13) 0.6957(2) 0.55991(11) 0.0332(5) Uani 1 1 d . . . . .
C14 C 0.22674(14) 0.6855(2) 0.59176(13) 0.0411(5) Uani 1 1 d . . . . .
H14A H 0.2256 0.7544 0.6279 0.049 Uiso 1 1 calc R . . . .
H14B H 0.1774 0.7001 0.5507 0.049 Uiso 1 1 calc R . . . .
C15 C 0.27389(13) 0.4989(2) 0.67267(11) 0.0318(4) Uani 1 1 d . . . . .
C16 C 0.12654(15) 0.5096(3) 0.62509(15) 0.0529(7) Uani 1 1 d . . . . .
H16 H 0.0723 0.5391 0.5984 0.063 Uiso 1 1 calc R . . . .
C17 C 0.13912(15) 0.4039(3) 0.66760(16) 0.0541(7) Uani 1 1 d . . . . .
H17 H 0.0952 0.3456 0.6760 0.065 Uiso 1 1 calc R . . . .
C18 C 0.26968(17) 0.2920(3) 0.74387(15) 0.0525(6) Uani 1 1 d . . . . .
H18A H 0.3332 0.2895 0.7433 0.079 Uiso 1 1 calc GR . . . .
H18B H 0.2430 0.2126 0.7246 0.079 Uiso 1 1 calc GR . . . .
H18C H 0.2591 0.3043 0.7948 0.079 Uiso 1 1 calc GR . . . .
O3 O 0.0530(2) 0.1309(3) 0.7251(2) 0.1162(10) Uani 1 1 d . . . . .
N10 N 0.09903(16) -0.0343(3) 0.80345(17) 0.0707(7) Uani 1 1 d . . . . .
C19 C 0.1151(2) -0.1198(4) 0.7436(2) 0.0943(12) Uani 1 1 d . . . . .
H19A H 0.1786 -0.1268 0.7437 0.141 Uiso 1 1 calc GR . . . .
H19B H 0.0864 -0.0866 0.6959 0.141 Uiso 1 1 calc GR . . . .
H19C H 0.0910 -0.2029 0.7517 0.141 Uiso 1 1 calc GR . . . .
C20 C 0.1211(3) -0.0804(5) 0.8800(2) 0.1110(14) Uani 1 1 d . . . . .
H20A H 0.0891 -0.1585 0.8852 0.166 Uiso 1 1 calc GR . . . .
H20B H 0.1043 -0.0173 0.9141 0.166 Uiso 1 1 calc GR . . . .
H20C H 0.1846 -0.0960 0.8917 0.166 Uiso 1 1 calc GR . . . .
C21 C 0.0696(2) 0.0836(4) 0.7877(3) 0.0877(11) Uani 1 1 d . . . . .
H21 H 0.0608 0.1349 0.8283 0.105 Uiso 1 1 calc R . . . .
O4 O 0.00040(18) 0.7459(3) 0.5447(2) 0.1216(11) Uani 1 1 d . . . . .
N11 N -0.09925(16) 0.9021(2) 0.51102(18) 0.0703(7) Uani 1 1 d . . . . .
C22 C -0.1096(3) 0.9346(5) 0.5856(3) 0.140(2) Uani 1 1 d . . . . .
H22A H -0.0742 0.8776 0.6205 0.210 Uiso 1 1 calc GR . . . .
H22B H -0.1717 0.9271 0.5909 0.210 Uiso 1 1 calc GR . . . .
H22C H -0.0899 1.0211 0.5961 0.210 Uiso 1 1 calc GR . . . .
C23 C -0.1554(3) 0.9673(4) 0.4490(3) 0.142(2) Uani 1 1 d . . . . .
H23A H -0.1406 0.9376 0.4018 0.213 Uiso 1 1 calc GR . . . .
H23B H -0.1453 1.0579 0.4534 0.213 Uiso 1 1 calc GR . . . .
H23C H -0.2175 0.9492 0.4507 0.213 Uiso 1 1 calc GR . . . .
C24 C -0.0457(2) 0.8105(4) 0.4986(2) 0.0801(10) Uani 1 1 d . . . . .
H24 H -0.0426 0.7928 0.4482 0.096 Uiso 1 1 calc R . . . .
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
N4 Ni1 N3 86.21(7) . . ?
C4 Ni1 N3 92.96(8) . . ?
C4 Ni1 N4 163.69(8) . . ?
C4 Ni1 C15 92.46(9) . . ?
C15 Ni1 N3 165.16(8) . . ?
C15 Ni1 N4 92.40(8) . . ?
C2 N1 C1 123.36(19) . . ?
C4 N1 C1 125.91(18) . . ?
C4 N1 C2 110.43(19) . . ?
C3 N2 C5 125.29(19) . . ?
C4 N2 C3 110.91(19) . . ?
C4 N2 C5 123.78(18) . . ?
C6 N3 Ni1 124.87(15) . . ?
C6 N3 C7 120.00(17) . . ?
C7 N3 Ni1 111.90(12) . . ?
C12 N4 Ni1 111.95(12) . . ?
C13 N4 Ni1 123.48(13) . . ?
C13 N4 C12 119.20(17) . . ?
C15 N5 C14 123.41(17) . . ?
C15 N5 C16 111.5(2) . . ?
C16 N5 C14 125.09(19) . . ?
C15 N6 C17 110.42(19) . . ?
C15 N6 C18 126.48(18) . . ?
C17 N6 C18 123.1(2) . . ?
C3 C2 N1 106.9(2) . . ?
C2 C3 N2 107.1(2) . . ?
N1 C4 Ni1 131.28(16) . . ?
N2 C4 Ni1 124.05(16) . . ?
N2 C4 N1 104.64(18) . . ?
N2 C5 C6 117.50(19) . . ?
O1 C6 N3 127.0(2) . . ?
O1 C6 C5 113.6(2) . . ?
N3 C6 C5 119.23(19) . . ?
C8 C7 N3 126.70(19) . . ?
C8 C7 C12 118.42(19) . . ?
C12 C7 N3 114.87(17) . . ?
C9 C8 C7 120.7(2) . . ?
C8 C9 Cl1 118.74(18) . . ?
C8 C9 C10 120.77(19) . . ?
C10 C9 Cl1 120.49(18) . . ?
C9 C10 Cl2 121.37(16) . . ?
C11 C10 Cl2 118.99(17) . . ?
C11 C10 C9 119.6(2) . . ?
C10 C11 C12 120.6(2) . . ?
C7 C12 N4 114.95(17) . . ?
C11 C12 N4 125.26(18) . . ?
C11 C12 C7 119.78(18) . . ?
O2 C13 N4 127.69(19) . . ?
O2 C13 C14 113.67(18) . . ?
N4 C13 C14 118.45(18) . . ?
N5 C14 C13 117.30(17) . . ?
N5 C15 Ni1 123.30(16) . . ?
N5 C15 N6 104.44(17) . . ?
N6 C15 Ni1 132.00(16) . . ?
C17 C16 N5 106.5(2) . . ?
C16 C17 N6 107.2(2) . . ?
C20 N10 C19 117.4(3) . . ?
C21 N10 C19 120.5(3) . . ?
C21 N10 C20 122.1(4) . . ?
O3 C21 N10 125.9(4) . . ?
C22 N11 C23 118.2(4) . . ?
C24 N11 C22 120.5(4) . . ?
C24 N11 C23 121.1(4) . . ?
O4 C24 N11 127.3(4) . . ?
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 N3 1.9084(16) . ?
Ni1 N4 1.9041(16) . ?
Ni1 C4 1.848(2) . ?
Ni1 C15 1.849(2) . ?
Cl1 C9 1.741(2) . ?
Cl2 C10 1.739(2) . ?
O1 C6 1.231(3) . ?
O2 C13 1.235(2) . ?
N1 C1 1.457(3) . ?
N1 C2 1.381(3) . ?
N1 C4 1.354(3) . ?
N2 C3 1.376(3) . ?
N2 C4 1.344(3) . ?
N2 C5 1.456(3) . ?
N3 C6 1.347(3) . ?
N3 C7 1.417(3) . ?
N4 C12 1.418(2) . ?
N4 C13 1.338(3) . ?
N5 C14 1.452(3) . ?
N5 C15 1.345(3) . ?
N5 C16 1.378(3) . ?
N6 C15 1.358(3) . ?
N6 C17 1.382(3) . ?
N6 C18 1.459(3) . ?
C2 C3 1.329(4) . ?
C5 C6 1.522(3) . ?
C7 C8 1.393(3) . ?
C7 C12 1.410(3) . ?
C8 C9 1.374(3) . ?
C9 C10 1.381(3) . ?
C10 C11 1.377(3) . ?
C11 C12 1.389(3) . ?
C13 C14 1.523(3) . ?
C16 C17 1.337(4) . ?
O3 C21 1.215(5) . ?
N10 C19 1.445(4) . ?
N10 C20 1.441(4) . ?
N10 C21 1.323(5) . ?
O4 C24 1.198(4) . ?
N11 C22 1.412(5) . ?
N11 C23 1.453(5) . ?
N11 C24 1.294(4) . ?
