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_7059477
_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_absolute_configuration syn
_chemical_formula_moiety         'C18 H28 N12 Ni, 2(C F3 O3 S)'
_chemical_formula_sum            'C20 H28 F6 N12 Ni O6 S2'
_chemical_formula_weight         769.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-11-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-11 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 131.427(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.009(2)
_cell_length_b                   9.6962(4)
_cell_length_c                   17.1351(17)
_cell_measurement_reflns_used    6120
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.7120
_cell_measurement_theta_min      3.2660
_cell_volume                     3115.5(9)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01(10)
_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  -35.00   29.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2518   77.0000   60.0000 64

  2 omega  -39.00   37.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2518   77.0000  150.0000 76

  3 omega    4.00   49.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1893   77.0000    0.0000 45

  4 omega    7.00   66.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1893   77.0000  -90.0000 59

  5 omega  -89.00  -30.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2518  146.0000  166.0000 59

  6 omega   23.00   71.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1893   57.0000   90.0000 48

  7 omega   17.00   75.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1893   57.0000 -180.0000 58

  8 omega   46.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1893 -178.0000   90.0000 52
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0295285000
_diffrn_orient_matrix_UB_12      -0.0335265000
_diffrn_orient_matrix_UB_13      -0.0110073000
_diffrn_orient_matrix_UB_21      0.0234766000
_diffrn_orient_matrix_UB_22      -0.0472970000
_diffrn_orient_matrix_UB_23      0.0410265000
_diffrn_orient_matrix_UB_31      0.0026695000
_diffrn_orient_matrix_UB_32      0.0445684000
_diffrn_orient_matrix_UB_33      0.0353158000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14306
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.171
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97344
_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    1.640
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.606(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         7034
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0310
_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/[\s^2^(Fo^2^)+(0.0299P)^2^+0.7591P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0710
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                6677
_reflns_number_total             7034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj00704h2.cif
_cod_data_source_block           737
_cod_depositor_comments
;Adding full bibliography for 7059474--7059481.cif.

 Adding full bibliography for 7059474--7059481.cif.
;
_cod_original_cell_volume        3115.5(7)
_cod_database_code               7059477
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'Ni1 N4 C10 H20 F3 S1'
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.905
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.394(11)
 0.606(11)
2. 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
3.a Aromatic/amide H refined with riding coordinates:
 N6(H6), C18(H18), C16(H16), C13(H13), C9(H9), C15(H15), N12(H12), C14(H14),
 C17(H17), C8(H8), C7(H7A), C5(H5), C6(H6A), C4(H4)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C3(H3A,H3B,H3C), C11(H11A,H11B,H11C), C2(H2A,H2B,H2C)
;
_shelx_res_checksum              40318
_olex2_submission_special_instructions 'No special instructions were received'