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_7059475
_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(N O3)'
_chemical_formula_sum            'C18 H28 N14 Ni O6'
_chemical_formula_weight         595.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                90
_cell_angle_beta                 103.297(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6235(7)
_cell_length_b                   8.0534(5)
_cell_length_c                   16.8565(12)
_cell_measurement_reflns_used    2277
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.7780
_cell_measurement_theta_min      4.8610
_cell_volume                     1271.39(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -104.00 -71.00   0.50    4.00    --  -41.10 -70.00-121.00   66
  2  \w    -56.00  22.00   0.50    4.00    --  -41.10  70.00   9.00  156
  3  \w    -61.00 -35.00   0.50    4.00    --  -41.10 -70.00-121.00   52
  4  \w     11.00  51.00   0.50    4.00    --   41.10 -70.00-121.00   80
  5  \w     65.00 112.00   0.50    9.40    --  101.00 -70.00-121.00   94
  6  \w     95.00 157.00   0.50    9.40    --  101.00  70.00   9.00  124
  7  \w    -50.00  -4.00   0.50    4.00    --  -41.10  32.00   0.00   92
  8  \w    -67.00 -34.00   0.50    4.00    --  -41.10 -32.00  90.00   66
  9  \w   -107.00 -72.00   0.50    4.00    --  -41.10 -32.00  90.00   70
 10  \w    -51.00  16.00   0.50    4.00    --  -41.10  21.00 -60.00  134
 11  \w   -109.00 -33.00   0.50    4.00    --  -41.10 -21.00 120.00  152
 12  \w     60.00  96.00   0.50    4.00    --   41.10  70.00   9.00   72
 13  \w     22.00  47.00   0.50    4.00    --   41.10  70.00   9.00   50
 14  \w    -12.00  33.00   0.50    4.00    --   41.10 -54.00 120.00   90
 15  \w     54.00  79.00   0.50    4.00    --   41.10  32.00   0.00   50
 16  \w     54.00 114.00   0.50    9.40    --  101.00 -42.00-150.00  120
 17  \w     68.00 105.00   0.50    9.40    --  101.00 -42.00 150.00   74
 18  \w     79.00 109.00   0.50    9.40    --  101.00 -77.00 120.00   60
 19  \w     92.00 124.00   0.50    9.40    --  101.00  33.00  30.00   64
 20  \w     84.00 116.00   0.50    9.40    --  101.00  59.00 120.00   64
 21  \w     94.00 152.00   0.50    9.40    --  101.00 111.00 -90.00  116
 22  \w     82.00 153.00   0.50    9.40    --  101.00 111.00 -60.00  142
 23  \w    132.00 157.00   0.50    9.40    --  101.00  77.00 -60.00   50
 24  \w     77.00 113.00   0.50    9.40    --  101.00  77.00 -60.00   72
 25  \w    100.00 157.00   0.50    9.40    --  101.00  25.00 -30.00  114
 26  \w     38.00  86.00   0.50    9.40    --  101.00 -50.00 -60.00   96
 27  \w    103.00 153.00   0.50    9.40    --  101.00  42.00  60.00  100
 28  \w     43.00  69.00   0.50    9.40    --  101.00 -77.00 120.00   52
 29  \w     30.00  61.00   0.50    9.40    --  101.00 -17.00  30.00   62
 30  \w     98.00 133.00   0.50    9.40    --  101.00  93.00 -30.00   70
 31  \w     38.00  93.00   0.50    9.40    --  101.00 -68.00-150.00  110
 32  \w    132.00 157.00   0.50    9.40    --  101.00  33.00-150.00   50
 33  \w     93.00 118.00   0.50    9.40    --  101.00  33.00-150.00   50
 34  \w     98.00 156.00   0.50    9.40    --  101.00  25.00 -60.00  116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1099903000
_diffrn_orient_matrix_UB_12      0.0854282000
_diffrn_orient_matrix_UB_13      -0.0688782000
_diffrn_orient_matrix_UB_21      0.0338483000
_diffrn_orient_matrix_UB_22      -0.1258890000
_diffrn_orient_matrix_UB_23      -0.0617494000
_diffrn_orient_matrix_UB_31      -0.1174971000
_diffrn_orient_matrix_UB_32      -0.1159151000
_diffrn_orient_matrix_UB_33      0.0163989000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6439
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.986
_diffrn_reflns_theta_min         4.869
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
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    1.555
_exptl_crystal_description       prism
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0305P)^2^+1.3880P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0932
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2088
_reflns_number_total             2399
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj00704h2.cif
_cod_data_source_block           m10
_cod_depositor_comments
;Adding full bibliography for 7059474--7059481.cif.

 Adding full bibliography for 7059474--7059481.cif.
;
_cod_database_code               7059475
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'Ni C27'
_reflns_odcompleteness_completeness 98.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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), C5(H5), C6(H6A), C4(H4), C7(H7), C9(H9), C8(H8)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_shelx_res_checksum              69204
_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 1.593
_oxdiff_exptl_absorpt_empirical_full_min 0.699