#------------------------------------------------------------------------------
#$Date: 2020-06-05 13:49:24 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252792 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/40/7704099.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_7704099
loop_
_publ_author_name
'Khatua, Manas'
'Goswami, Bappaditya'
'Samanta, Subhas'
_publ_section_title
;
 Dehydrogenation of amines in aryl-amine functionalized pincer-like
 nitrogen-donor redox non-innocent ligands via ligand reduction on a
 Ni(ii) template.
;
_journal_issue                   20
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6816
_journal_page_last               6831
_journal_paper_doi               10.1039/d0dt00466a
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C24 H28 Cl2 N4 Ni'
_chemical_formula_sum            'C24 H28 Cl2 N4 Ni'
_chemical_formula_weight         502.09
_chemical_name_systematic        1
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-14 deposited with the CCDC.	2020-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                107.115(7)
_cell_angle_beta                 90.214(5)
_cell_angle_gamma                100.707(6)
_cell_formula_units_Z            2
_cell_length_a                   9.4290(5)
_cell_length_b                   10.4037(8)
_cell_length_c                   12.8727(8)
_cell_measurement_reflns_used    3978
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      26.7470
_cell_measurement_theta_min      2.2270
_cell_volume                     1183.54(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.859
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  90.00   1.00   10.00    --   25.18  57.00   0.00   94
  2  ω      8.00  89.00   1.00   10.00    --   25.18  77.00-120.00   81
  3  ω     85.00 113.00   1.00   10.00    --   25.18 178.00-120.00   28
  4  ω    -34.00  79.00   1.00   10.00    --   25.18 -38.00  90.00  113
  5  ω     -5.00  32.00   1.00   10.00    --  -23.50 -99.00 -30.00   37
  6  ω    -49.00  34.00   1.00   10.00    --   25.18 -38.00  30.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7169
_diffrn_reflns_theta_full        27.12
_diffrn_reflns_theta_max         27.12
_diffrn_reflns_theta_min         1.66
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.064
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0219P)²+0.6964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0862
_reflns_number_gt                3893
_reflns_number_total             4489
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0dt00466a2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7704099--7704110.cif.'
_cod_original_cell_volume        1183.54(13)
_cod_database_code               7704099
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Fixed occupancy and ADP/Uiso:
 H4
2.b Ternary CH refined with riding coordinates:
 C19(H19), C22(H22)
2.c Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b)
2.d Aromatic/amide H refined with riding coordinates:
 C17(H17), C16(H16), C15(H15), C8(H8), C9(H9), C3(H3), C10(H10), C1(H1),
 C5(H5), C4(H4a), C2(H2)
2.e Idealised Me refined as rotating group:
 C23(H23a,H23b,H23c), C24(H24a,H24b,H24c), C20(H20a,H20b,H20c), 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 1.356
_oxdiff_exptl_absorpt_empirical_full_min 0.813
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Ni1 Ni 0.34164(3) 0.46706(3) 0.73645(3) 0.01503(10) Uani 1 d . . .
Cl2 Cl 0.13535(6) 0.35238(6) 0.77771(5) 0.02236(16) Uani 1 d . . .
Cl1 Cl 0.37030(7) 0.61460(6) 0.63451(5) 0.02340(16) Uani 1 d . . .
N4 N 0.4027(2) 0.3105(2) 0.59795(17) 0.0156(5) Uani 1 d . . .
H4 H 0.397(3) 0.360(3) 0.561(2) 0.019 Uiso 1 d . . .
N3 N 0.5397(2) 0.4703(2) 0.78548(16) 0.0148(4) Uani 1 d . . .
N1 N 0.3796(2) 0.6259(2) 0.89026(16) 0.0160(4) Uani 1 d . . .
N2 N 0.4978(2) 0.6405(2) 0.94355(16) 0.0171(5) Uani 1 d . . .
C7 C 0.5893(3) 0.5543(3) 0.8848(2) 0.0161(5) Uani 1 d . . .
C17 C 0.1390(3) 0.0368(3) 0.3977(2) 0.0184(5) Uani 1 d . . .
H17 H 0.0810 0.0256 0.3340 0.022 Uiso 1 calc . . R
C16 C 0.1335(3) -0.0731(3) 0.4381(2) 0.0197(6) Uani 1 d . . .
H16 H 0.0758 -0.1598 0.4008 0.024 Uiso 1 calc . . R
C12 C 0.5586(3) 0.3061(3) 0.6118(2) 0.0166(5) Uani 1 d . . .
H12A H 0.6124 0.3394 0.5558 0.020 Uiso 1 calc . . R
H12B H 0.5688 0.2100 0.6005 0.020 Uiso 1 calc . . R
C11 C 0.6236(3) 0.3928(2) 0.7234(2) 0.0152(5) Uani 1 d . . .
C18 C 0.2277(3) 0.1640(3) 0.4483(2) 0.0163(5) Uani 1 d . . .
C15 C 0.2132(3) -0.0551(3) 0.5339(2) 0.0192(6) Uani 1 d . . .
H15 H 0.2094 -0.1309 0.5615 0.023 Uiso 1 calc . . R
C19 C 0.2266(3) 0.2803(3) 0.3990(2) 0.0195(6) Uani 1 d . . .
H19 H 0.3135 0.3532 0.4314 0.023 Uiso 1 calc . . R
C22 C 0.3711(3) 0.0848(3) 0.7006(2) 0.0168(5) Uani 1 d . . .
H22 H 0.4184 0.1829 0.7346 0.020 Uiso 1 calc . . R
C8 C 0.7252(3) 0.5621(3) 0.9289(2) 0.0197(6) Uani 1 d . . .
H8 H 0.7575 0.6207 1.0000 0.024 Uiso 1 calc . . R
C9 C 0.8133(3) 0.4809(3) 0.8651(2) 0.0214(6) Uani 1 d . . .
H9 H 0.9075 0.4827 0.8926 0.026 Uiso 1 calc . . R
C14 C 0.2990(2) 0.0711(2) 0.5908(2) 0.0157(5) Uani 1 d . . .
C6 C 0.2843(3) 0.7112(3) 0.9446(2) 0.0178(5) Uani 1 d . . .
C3 C 0.0855(3) 0.8655(3) 1.0418(2) 0.0266(6) Uani 1 d . . .
H3 H 0.0165 0.9178 1.0756 0.032 Uiso 1 calc . . R
C10 C 0.7636(3) 0.3974(3) 0.7615(2) 0.0200(6) Uani 1 d . . .
H10 H 0.8243 0.3437 0.7168 0.024 Uiso 1 calc . . R
C13 C 0.3090(2) 0.1792(2) 0.54427(19) 0.0144(5) Uani 1 d . . .
C23 C 0.4871(3) -0.0030(3) 0.6877(2) 0.0222(6) Uani 1 d . . .
H23A H 0.4441 -0.0987 0.6488 0.033 Uiso 1 calc . . GR
H23B H 0.5268 0.0028 0.7597 0.033 Uiso 1 calc . . GR
H23C H 0.5647 0.0305 0.6462 0.033 Uiso 1 calc . . GR
C1 C 0.1634(3) 0.7139(3) 0.8832(2) 0.0228(6) Uani 1 d . . .
H1 H 0.1487 0.6623 0.8083 0.027 Uiso 1 calc . . R
C24 C 0.2597(3) 0.0430(3) 0.7775(2) 0.0244(6) Uani 1 d . . .
H24A H 0.1812 0.0939 0.7819 0.037 Uiso 1 calc . . GR
H24B H 0.3068 0.0640 0.8502 0.037 Uiso 1 calc . . GR
H24C H 0.2202 -0.0556 0.7495 0.037 Uiso 1 calc . . GR
C5 C 0.3060(3) 0.7869(3) 1.0539(2) 0.0237(6) Uani 1 d . . .
H5 H 0.3896 0.7864 1.0951 0.028 Uiso 1 calc . . R
C4 C 0.2058(3) 0.8628(3) 1.1023(2) 0.0289(7) Uani 1 d . . .
H4A H 0.2193 0.9133 1.1774 0.035 Uiso 1 calc . . R
C2 C 0.0651(3) 0.7929(3) 0.9328(2) 0.0261(6) Uani 1 d . . .
H2 H -0.0167 0.7970 0.8915 0.031 Uiso 1 calc . . R
C20 C 0.2381(3) 0.2352(3) 0.2757(2) 0.0337(7) Uani 1 d . . .
H20A H 0.3283 0.2017 0.2586 0.051 Uiso 1 calc . . GR
H20B H 0.2375 0.3132 0.2480 0.051 Uiso 1 calc . . GR
H20C H 0.1557 0.1616 0.2416 0.051 Uiso 1 calc . . GR
C21 C 0.0933(3) 0.3436(3) 0.4298(3) 0.0411(8) Uani 1 d . . .
H21A H 0.0060 0.2752 0.3978 0.062 Uiso 1 calc . . GR
H21B H 0.0982 0.4225 0.4022 0.062 Uiso 1 calc . . GR
H21C H 0.0900 0.3738 0.5093 0.062 Uiso 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'
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'
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
Cl2 Ni1 Cl1 128.19(3) . . ?
N4 Ni1 Cl2 101.41(6) . . ?
N4 Ni1 Cl1 88.93(6) . . ?
N3 Ni1 Cl2 127.89(6) . . ?
N3 Ni1 Cl1 103.87(6) . . ?
N3 Ni1 N4 79.42(8) . . ?
N3 Ni1 N1 75.49(8) . . ?
N1 Ni1 Cl2 95.85(6) . . ?
N1 Ni1 Cl1 94.75(6) . . ?
N1 Ni1 N4 154.80(8) . . ?
Ni1 N4 H4 88(2) . . ?
C12 N4 Ni1 110.11(14) . . ?
C12 N4 H4 107.8(19) . . ?
C13 N4 Ni1 123.77(15) . . ?
C13 N4 H4 107(2) . . ?
C13 N4 C12 115.34(19) . . ?
C7 N3 Ni1 117.55(16) . . ?
C11 N3 Ni1 121.93(17) . . ?
C11 N3 C7 120.5(2) . . ?
N2 N1 Ni1 116.70(16) . . ?
N2 N1 C6 114.8(2) . . ?
C6 N1 Ni1 128.28(16) . . ?
N1 N2 C7 112.4(2) . . ?
N3 C7 N2 117.5(2) . . ?
N3 C7 C8 122.6(2) . . ?
C8 C7 N2 119.9(2) . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.6(2) . . ?
C18 C17 H17 119.2 . . ?
C17 C16 H16 120.4 . . ?
C17 C16 C15 119.2(2) . . ?
C15 C16 H16 120.4 . . ?
N4 C12 H12A 109.2 . . ?
N4 C12 H12B 109.2 . . ?
N4 C12 C11 111.85(19) . . ?
H12A C12 H12B 107.9 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
N3 C11 C12 116.0(2) . . ?
N3 C11 C10 120.2(2) . . ?
C10 C11 C12 123.8(2) . . ?
C17 C18 C19 118.3(2) . . ?
C17 C18 C13 118.1(2) . . ?
C13 C18 C19 123.5(2) . . ?
C16 C15 H15 119.1 . . ?
C16 C15 C14 121.8(2) . . ?
C14 C15 H15 119.1 . . ?
C18 C19 H19 107.4 . . ?
C18 C19 C20 112.5(2) . . ?
C18 C19 C21 110.7(2) . . ?
C20 C19 H19 107.4 . . ?
C21 C19 H19 107.4 . . ?
C21 C19 C20 111.2(2) . . ?
C14 C22 H22 108.4 . . ?
C14 C22 C23 111.3(2) . . ?
C14 C22 C24 111.3(2) . . ?
C23 C22 H22 108.4 . . ?
C23 C22 C24 109.0(2) . . ?
C24 C22 H22 108.4 . . ?
C7 C8 H8 121.3 . . ?
C7 C8 C9 117.4(2) . . ?
C9 C8 H8 121.3 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C15 C14 C22 118.1(2) . . ?
C15 C14 C13 117.6(2) . . ?
C13 C14 C22 124.3(2) . . ?
C1 C6 N1 116.7(2) . . ?
C5 C6 N1 122.9(2) . . ?
C5 C6 C1 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 C11 119.3(2) . . ?
C9 C10 H10 120.3 . . ?
C18 C13 N4 119.1(2) . . ?
C18 C13 C14 121.4(2) . . ?
C14 C13 N4 119.5(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C6 C1 H1 120.5 . . ?
C2 C1 C6 119.1(2) . . ?
C2 C1 H1 120.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.2 . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4A 120.0 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 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 Cl2 2.2376(7) . ?
Ni1 Cl1 2.2771(7) . ?
Ni1 N4 2.193(2) . ?
Ni1 N3 1.961(2) . ?
Ni1 N1 2.152(2) . ?
N4 H4 0.80(3) . ?
N4 C12 1.491(3) . ?
N4 C13 1.454(3) . ?
N3 C7 1.343(3) . ?
N3 C11 1.332(3) . ?
N1 N2 1.267(3) . ?
N1 C6 1.421(3) . ?
N2 C7 1.419(3) . ?
C7 C8 1.378(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.381(4) . ?
C17 C18 1.397(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.388(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.510(3) . ?
C11 C10 1.394(3) . ?
C18 C19 1.525(4) . ?
C18 C13 1.403(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.397(3) . ?
C19 H19 1.0000 . ?
C19 C20 1.527(4) . ?
C19 C21 1.526(4) . ?
C22 H22 1.0000 . ?
C22 C14 1.523(3) . ?
C22 C23 1.530(3) . ?
C22 C24 1.538(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(4) . ?
C14 C13 1.410(3) . ?
C6 C1 1.394(4) . ?
C6 C5 1.388(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(4) . ?
C3 C2 1.377(4) . ?
C10 H10 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C1 H1 0.9500 . ?
C1 C2 1.387(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C5 H5 0.9500 . ?
C5 C4 1.377(4) . ?
C4 H4A 0.9500 . ?
C2 H2 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
