#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:04:38 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257734 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/94/7059476.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_7059476
loop_
_publ_author_name
'Zelenkov, Lev E.'
'Kuznetsov, Maxim L.'
'Andrusenko, Elena V.'
'Avdontceva, Margarita S.'
'Starova, Galina L.'
'Bokach, Nadezhda A.'
'Kukushkin, Vadim Yu.'
_publ_section_title
;
 Nickel(ii)-mediated cyanamide--pyrazole coupling highlights distinct
 reactivity of NCNR2 and NCR nitrile ligands
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6979
_journal_page_last               6991
_journal_paper_doi               10.1039/D0NJ00704H
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C22 H36 N12 Ni, 2(C F3 O3 S)'
_chemical_formula_sum            'C24 H36 F6 N12 Ni O6 S2'
_chemical_formula_weight         825.48
_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     dual
_audit_creation_date             2019-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-10 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                101.057(8)
_cell_angle_beta                 101.885(6)
_cell_angle_gamma                111.644(7)
_cell_formula_units_Z            1
_cell_length_a                   9.6380(6)
_cell_length_b                   10.2071(9)
_cell_length_c                   10.3141(9)
_cell_measurement_reflns_used    4746
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.1560
_cell_measurement_theta_min      3.7170
_cell_volume                     882.01(14)
_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      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  14.00   1.00   32.19    --  -14.18 -57.00   0.00   27
  2  ω    -11.00  15.00   1.00   32.19    --  -14.18 -99.00 -60.00   26
  3  ω    -82.00 -55.00   1.00   32.19    --  -14.18 -57.00   0.00   27
  4  ω    -55.00  43.00   1.00   32.19    --   16.06 -57.00 150.00   98
  5  ω    -11.00  74.00   1.00   32.19    --   16.06  57.00  90.00   85
  6  ω     -8.00  85.00   1.00   32.19    --   16.06  57.00 -60.00   93
  7  ω    -42.00   1.00   1.00   32.19    --  -14.18 -38.00 120.00   43
  8  ω    -42.00   2.00   1.00   32.19    --   16.06 -77.00 -90.00   44
  9  ω     13.00  80.00   1.00   32.19    --   16.06  38.00-180.00   67
 10  ω    -57.00  39.00   1.00   32.19    --   16.06 -38.00   0.00   96
 11  ω      1.00  72.00   1.00   32.19    --   18.00-121.00  98.34   71
 12  ω     20.00  85.00   1.00   32.19    --   18.00-142.00 -25.42   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0047922000
_diffrn_orient_matrix_UB_12      -0.0171285000
_diffrn_orient_matrix_UB_13      -0.0712203000
_diffrn_orient_matrix_UB_21      -0.0536746000
_diffrn_orient_matrix_UB_22      -0.0736368000
_diffrn_orient_matrix_UB_23      -0.0105160000
_diffrn_orient_matrix_UB_31      -0.0632458000
_diffrn_orient_matrix_UB_32      0.0200955000
_diffrn_orient_matrix_UB_33      -0.0149795000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15571
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.222
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66592
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_description       prism
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.127
_refine_diff_density_min         -0.990
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         4053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0545
_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)+(0.0709P)²+1.0544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1487
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3326
_reflns_number_total             4053
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj00704h2.cif
_cod_data_source_block           0m05
_cod_depositor_comments
;Adding full bibliography for 7059474--7059481.cif.

 Adding full bibliography for 7059474--7059481.cif.
;
_cod_original_cell_volume        882.01(13)
_cod_database_code               7059476
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 N12 O6 F6 Ni'
_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 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.64
_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 Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), N6(H6), C6(H6A), C4(H4), C5(H5), C9(H9), C8(H8)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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 1.521
_oxdiff_exptl_absorpt_empirical_full_min 0.594
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_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 0.500000 0.500000 0.500000 0.01962(16) Uani 1 2 d S T P . .
S1 S 0.28119(8) 0.88361(9) 0.27266(8) 0.0264(2) Uani 1 1 d . . . . .
F2 F 0.4790(2) 0.9993(2) 0.1423(2) 0.0418(5) Uani 1 1 d . . . . .
F1 F 0.2947(2) 0.7865(3) 0.0228(2) 0.0468(6) Uani 1 1 d . . . . .
F3 F 0.2467(2) 0.9775(3) 0.0551(2) 0.0447(5) Uani 1 1 d . . . . .
O1 O 0.3879(3) 0.8258(3) 0.3300(2) 0.0343(5) Uani 1 1 d . . . . .
N5 N 0.3080(3) 0.4167(3) 0.3202(3) 0.0248(5) Uani 1 1 d . . . . .
O3 O 0.1190(3) 0.7795(3) 0.2223(3) 0.0441(6) Uani 1 1 d . . . . .
N3 N 0.7225(3) 0.5452(3) 0.3490(2) 0.0221(5) Uani 1 1 d . . . . .
O2 O 0.3143(3) 1.0310(3) 0.3504(3) 0.0434(6) Uani 1 1 d . . . . .
N1 N 0.6061(3) 0.6827(3) 0.4394(2) 0.0221(5) Uani 1 1 d . . . . .
H1 H 0.593571 0.761917 0.464274 0.027 Uiso 1 1 calc R . . . .
N4 N 0.6306(3) 0.4303(3) 0.3875(2) 0.0228(5) Uani 1 1 d . . . . .
N2 N 0.7645(3) 0.7681(3) 0.2978(3) 0.0266(5) Uani 1 1 d . . . . .
C7 C 0.2275(4) 0.2737(4) 0.2484(3) 0.0313(7) Uani 1 1 d . . . . .
H7 H 0.246838 0.197029 0.271605 0.038 Uiso 1 1 calc R . . . .
N6 N 0.2458(4) 0.4921(4) 0.2519(3) 0.0429(8) Uani 1 1 d . . . . .
H6 H 0.277630 0.586311 0.276429 0.051 Uiso 1 1 calc R . . . .
C1 C 0.6921(3) 0.6714(3) 0.3625(3) 0.0228(6) Uani 1 1 d . . . . .
C6 C 0.6924(4) 0.3347(4) 0.3773(3) 0.0286(6) Uani 1 1 d . . . . .
H6A H 0.653028 0.245233 0.396850 0.034 Uiso 1 1 calc R . . . .
C4 C 0.8448(3) 0.5210(4) 0.3182(3) 0.0281(7) Uani 1 1 d . . . . .
H4 H 0.924599 0.584516 0.292373 0.034 Uiso 1 1 calc R . . . .
C5 C 0.8268(4) 0.3864(4) 0.3327(3) 0.0326(7) Uani 1 1 d . . . . .
H5 H 0.889723 0.338443 0.316665 0.039 Uiso 1 1 calc R . . . .
C2 C 0.7774(4) 0.9181(4) 0.3476(4) 0.0307(7) Uani 1 1 d . . . . .
H2A H 0.796740 0.944329 0.447181 0.037 Uiso 1 1 calc R . . . .
H2B H 0.678976 0.920532 0.305466 0.037 Uiso 1 1 calc R . . . .
C12 C 0.3276(4) 0.9121(4) 0.1154(3) 0.0297(7) Uani 1 1 d . . . . .
C3 C 0.7447(4) 0.7117(4) 0.1480(3) 0.0310(7) Uani 1 1 d . . . . .
H3A H 0.740763 0.613346 0.129105 0.037 Uiso 1 1 calc R . . . .
H3B H 0.835118 0.774545 0.126649 0.037 Uiso 1 1 calc R . . . .
C10 C 0.5972(4) 0.7061(4) 0.0541(4) 0.0379(8) Uani 1 1 d . . . . .
H10A H 0.581674 0.655456 -0.039975 0.057 Uiso 1 1 calc GR . . . .
H10B H 0.608189 0.804743 0.060394 0.057 Uiso 1 1 calc GR . . . .
H10C H 0.508626 0.654728 0.082503 0.057 Uiso 1 1 calc GR . . . .
C11 C 0.9091(4) 1.0309(4) 0.3131(4) 0.0403(8) Uani 1 1 d . . . . .
H11A H 0.875659 1.024910 0.216955 0.060 Uiso 1 1 calc GR . . . .
H11B H 0.999775 1.010720 0.331427 0.060 Uiso 1 1 calc GR . . . .
H11C H 0.934815 1.128210 0.369290 0.060 Uiso 1 1 calc GR . . . .
C9 C 0.1230(5) 0.3942(7) 0.1365(4) 0.0640(16) Uani 1 1 d . . . . .
H9 H 0.060047 0.417458 0.072203 0.077 Uiso 1 1 calc R . . . .
C8 C 0.1121(5) 0.2577(7) 0.1351(4) 0.0665(16) Uani 1 1 d . . . . .
H8 H 0.039763 0.169358 0.069416 0.080 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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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
N5 Ni1 N5 180.0 . 2_666 ?
N1 Ni1 N5 90.17(10) 2_666 2_666 ?
N1 Ni1 N5 89.83(10) 2_666 . ?
N1 Ni1 N5 90.17(10) . . ?
N1 Ni1 N5 89.83(10) . 2_666 ?
N1 Ni1 N1 180.0 2_666 . ?
N1 Ni1 N4 101.05(9) 2_666 . ?
N1 Ni1 N4 78.95(9) 2_666 2_666 ?
N1 Ni1 N4 101.05(9) . 2_666 ?
N1 Ni1 N4 78.95(9) . . ?
N4 Ni1 N5 90.87(9) 2_666 2_666 ?
N4 Ni1 N5 90.87(9) . . ?
N4 Ni1 N5 89.13(9) . 2_666 ?
N4 Ni1 N5 89.13(9) 2_666 . ?
N4 Ni1 N4 180.00(16) 2_666 . ?
O1 S1 O2 114.82(15) . . ?
O1 S1 C12 103.48(14) . . ?
O3 S1 O1 114.51(15) . . ?
O3 S1 O2 116.14(16) . . ?
O3 S1 C12 103.25(15) . . ?
O2 S1 C12 102.02(16) . . ?
C7 N5 Ni1 124.5(2) . . ?
C7 N5 N6 107.1(3) . . ?
N6 N5 Ni1 128.4(2) . . ?
N4 N3 C1 118.4(2) . . ?
N4 N3 C4 110.5(2) . . ?
C4 N3 C1 130.6(3) . . ?
C1 N1 Ni1 115.9(2) . . ?
N3 N4 Ni1 109.38(17) . . ?
C6 N4 Ni1 140.1(2) . . ?
C6 N4 N3 106.0(2) . . ?
C1 N2 C2 115.5(2) . . ?
C1 N2 C3 118.4(3) . . ?
C2 N2 C3 117.1(2) . . ?
N5 C7 C8 109.5(4) . . ?
N5 N6 C9 109.3(4) . . ?
N1 C1 N3 115.6(3) . . ?
N1 C1 N2 128.7(3) . . ?
N2 C1 N3 115.6(2) . . ?
N4 C6 C5 110.9(3) . . ?
C5 C4 N3 106.9(3) . . ?
C4 C5 C6 105.7(3) . . ?
N2 C2 C11 111.9(3) . . ?
F2 C12 S1 111.3(2) . . ?
F2 C12 F3 106.9(3) . . ?
F1 C12 S1 112.3(2) . . ?
F1 C12 F2 107.7(2) . . ?
F1 C12 F3 107.4(3) . . ?
F3 C12 S1 110.9(2) . . ?
N2 C3 C10 112.9(3) . . ?
C8 C9 N6 106.7(4) . . ?
C9 C8 C7 107.4(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 N5 2.099(2) 2_666 ?
Ni1 N5 2.099(2) . ?
Ni1 N1 2.054(2) . ?
Ni1 N1 2.054(2) 2_666 ?
Ni1 N4 2.093(2) 2_666 ?
Ni1 N4 2.093(2) . ?
S1 O1 1.444(2) . ?
S1 O3 1.439(2) . ?
S1 O2 1.445(3) . ?
S1 C12 1.817(3) . ?
F2 C12 1.334(4) . ?
F1 C12 1.327(4) . ?
F3 C12 1.335(4) . ?
N5 C7 1.340(4) . ?
N5 N6 1.350(4) . ?
N3 N4 1.369(3) . ?
N3 C1 1.411(4) . ?
N3 C4 1.375(3) . ?
N1 C1 1.279(4) . ?
N4 C6 1.316(4) . ?
N2 C1 1.358(4) . ?
N2 C2 1.468(4) . ?
N2 C3 1.487(4) . ?
C7 C8 1.374(6) . ?
N6 C9 1.381(6) . ?
C6 C5 1.415(4) . ?
C4 C5 1.362(5) . ?
C2 C11 1.526(4) . ?
C3 C10 1.522(4) . ?
C9 C8 1.355(8) . ?
