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_7059478
_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 H32 N12 Ni, 2(C F3 O3 S), 2(C3 H6 O)'
_chemical_formula_sum            'C30 H44 F6 N12 Ni O8 S2'
_chemical_formula_weight         937.60
_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             2019-11-18
_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                82.723(5)
_cell_angle_beta                 72.312(5)
_cell_angle_gamma                84.509(4)
_cell_formula_units_Z            1
_cell_length_a                   8.7256(4)
_cell_length_b                   10.0265(6)
_cell_length_c                   12.2050(7)
_cell_measurement_reflns_used    3106
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.3880
_cell_measurement_theta_min      3.2930
_cell_volume                     1007.26(10)
_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 0.998
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_details
;
  1 omega  -43.00   31.00   1.0000    5.2000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803   57.0000   60.0000 74

  2 omega  -79.00   -7.00   1.0000    5.2000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  123.0000   71.0000 72

  3 omega   35.00   74.00   1.0000    5.2000
omega____ theta____ kappa____ phi______ frames
    -       23.5178 -123.0000   -8.0000 39

  4 omega  -45.00   38.00   1.0000    5.2000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -57.0000 -180.0000 83

  5 omega   38.00   63.00   1.0000    5.2000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -99.0000 -150.0000 25

  6 omega  -21.00   96.00   1.0000    5.2000
omega____ theta____ kappa____ phi______ frames
    -       23.5178   19.0000    0.0000 117

  7 omega   -7.00   18.00   1.0000    5.2000
omega____ theta____ kappa____ phi______ frames
    -       23.5178   77.0000   60.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0108163000
_diffrn_orient_matrix_UB_12      -0.0286184000
_diffrn_orient_matrix_UB_13      -0.0522874000
_diffrn_orient_matrix_UB_21      0.0440816000
_diffrn_orient_matrix_UB_22      0.0555520000
_diffrn_orient_matrix_UB_23      -0.0315460000
_diffrn_orient_matrix_UB_31      0.0724335000
_diffrn_orient_matrix_UB_32      -0.0346378000
_diffrn_orient_matrix_UB_33      0.0056251000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10085
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.972
_diffrn_reflns_theta_min         2.838
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92561
_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    1.546
_exptl_crystal_description       prism
_exptl_crystal_F_000             486
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         5621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0257P)^2^+0.6030P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0808
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4685
_reflns_number_total             5621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj00704h2.cif
_cod_data_source_block           11255-m-34
_cod_depositor_comments
;Adding full bibliography for 7059474--7059481.cif.

 Adding full bibliography for 7059474--7059481.cif.
;
_cod_database_code               7059478
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 H10 N2 Ni1'
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.923
_reflns_odcompleteness_completeness 99.90
_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 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), C11(H11A,H11B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N6(H6), C7(H7), C4(H4), C6(H6A), C8(H8), C5(H5), C9(H9)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              70985
_olex2_submission_special_instructions 'No special instructions were received'