Nickel(ii)-mediated cyanamide–pyrazole coupling highlights distinct reactivity of NCNR2 and NCR nitrile ligands
Zelenkov, Lev E.; Kuznetsov, Maxim L.; Andrusenko, Elena V.; Avdontceva, Margarita S.; Starova, Galina L.; Bokach, Nadezhda A.; Kukushkin, Vadim Yu.; New Journal of Chemistry 44 (2020) 6979–6991; doi:10.1039/D0NJ00704H

data_7059481
_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         'C18 H28 N12 Ni, 2(Cl)'
_chemical_formula_sum            'C18 H28 Cl2 N12 Ni'
_chemical_formula_weight         542.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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
;
2019-11-18 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 126.983(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.9358(11)
_cell_length_b                   9.2467(3)
_cell_length_c                   16.9617(10)
_cell_measurement_reflns_used    4877
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7020
_cell_measurement_theta_min      3.0350
_cell_volume                     2497.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -14.00   19.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000  150.0000 33

  2 omega  -89.00  -14.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -57.0000   30.0000 75

  3 omega  -89.00  -43.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -      -22.2678 -178.0000  150.0000 46

  4 omega  -24.00    2.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000   90.0000 26

  5 omega   55.00   88.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000 -180.0000 33

  6 omega   41.00   98.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -178.0000   60.0000 57

  7 omega   22.00   48.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -      -22.2678   38.0000 -150.0000 26

  8 omega  -62.00  -37.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -      -22.2678 -178.0000  -30.0000 25

  9 omega  -90.00  -48.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -57.0000 -120.0000 42

 10 omega  -90.00  -65.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -77.0000  -60.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0202453000
_diffrn_orient_matrix_UB_12      -0.0055236000
_diffrn_orient_matrix_UB_13      -0.0228046000
_diffrn_orient_matrix_UB_21      0.0242035000
_diffrn_orient_matrix_UB_22      -0.0588531000
_diffrn_orient_matrix_UB_23      0.0313335000
_diffrn_orient_matrix_UB_31      -0.0314565000
_diffrn_orient_matrix_UB_32      -0.0488456000
_diffrn_orient_matrix_UB_33      -0.0352275000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9275
_diffrn_reflns_point_group_measured_fraction_full 0.999
_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         2.547
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.023
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.442
_exptl_crystal_description       prism
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0302
_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/[\s^2^(Fo^2^)+(0.0264P)^2^+3.2709P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0715
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2605
_reflns_number_total             2868
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj00704h2.cif
_cod_data_source_block           08310-8516_m11
_cod_depositor_comments
;Adding full bibliography for 7059474--7059481.cif.

 Adding full bibliography for 7059474--7059481.cif.
;
_cod_database_code               7059481
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 Cl2 Cu N12'
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.896
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N6(H6), C7(H7), C4(H4), C5(H5), C8(H8), C6(H6A), C9(H9)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_shelx_res_checksum              30341
_olex2_submission_special_instructions 'No special instructions were received'