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_7059480
_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         'C24 H36 N12 Ni, 2(N O3)'
_chemical_formula_sum            'C24 H36 N14 Ni O6'
_chemical_formula_weight         675.38
_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   mixed
_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
;
2020-03-10 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.938(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3309(4)
_cell_length_b                   9.7597(4)
_cell_length_c                   18.0944(11)
_cell_measurement_reflns_used    2105
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.0160
_cell_measurement_theta_min      4.9440
_cell_volume                     1453.34(13)
_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 0.998
_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    -67.00  35.00   1.00   15.00    --  -40.38  38.00-120.00  102
  2  \w    -67.00  26.00   1.00   15.00    --  -40.38  38.00 150.00   93
  3  \w     90.00 129.00   1.00   15.00    --   40.38 178.00 -60.00   39
  4  \w     96.00 125.00   1.00   15.00    --   40.38 178.00-150.00   29
  5  \w     85.00 115.00   1.00   45.00    --  113.00-112.00-120.00   30
  6  \w    103.00 167.00   1.00   45.00    --  113.00 112.00   0.00   64
  7  \w     86.00 172.00   1.00   45.00    --  113.00  45.00-180.00   86
  8  \w     50.00 106.00   1.00   45.00    --  113.00 -95.00   0.00   56
  9  \w     42.00  97.00   1.00   45.00    --  113.00 -95.00 -30.00   55
 10  \w    107.00 148.00   1.00   45.00    --  113.00 112.00 -90.00   41
 11  \w     41.00 139.00   1.00   45.00    --  113.00 -45.00   0.00   98
 12  \w     81.00 140.00   1.00   45.00    --  113.00 178.00 -60.00   59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1067778000
_diffrn_orient_matrix_UB_12      0.1264212000
_diffrn_orient_matrix_UB_13      0.0231202000
_diffrn_orient_matrix_UB_21      0.1369846000
_diffrn_orient_matrix_UB_22      -0.0940812000
_diffrn_orient_matrix_UB_23      0.0379192000
_diffrn_orient_matrix_UB_31      0.0697851000
_diffrn_orient_matrix_UB_32      -0.0085621000
_diffrn_orient_matrix_UB_33      -0.0738896000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5574
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.487
_diffrn_reflns_theta_max         67.487
_diffrn_reflns_theta_min         4.948
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.540
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62332
_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    1.543
_exptl_crystal_description       prism
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0700
_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^)+(0.0786P)^2^+3.0428P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1762
_refine_ls_wR_factor_ref         0.1860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2186
_reflns_number_total             2612
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj00704h2.cif
_cod_data_source_block           0ver0-9022_m17
_cod_depositor_comments
;Adding full bibliography for 7059474--7059481.cif.

 Adding full bibliography for 7059474--7059481.cif.
;
_cod_database_code               7059480
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C24 N14 Ni O6'
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.861
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C10) = Uanis(C10')
3. Others
 Fixed Sof: C10(0.7) H10A(0.7) H10B(0.7) C2'(0.6) H2'A(0.6) H2'B(0.6) C3'(0.6)
 H3'A(0.6) H3'B(0.6) C12(0.6) H12A(0.6) H12B(0.6) C3(0.4) H3A(0.4) H3B(0.4)
 C2(0.4) H2A(0.4) H2B(0.4) C12'(0.4) H12C(0.4) H12D(0.4) C10'(0.3) H10C(0.3)
 H10D(0.3)
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C2'(H2'A,H2'B), C3'(H3'A,H3'B), C12(H12A,H12B), C3(H3A,H3B),
 C2(H2A,H2B), C12'(H12C,H12D), C10'(H10C,H10D)
4.b Aromatic/amide H refined with riding coordinates:
 N6(H6), N1(H1), C8(H8), C7(H7), C9(H9), C6(H6A), C5(H5), C4(H4), C11(H11A)
;
_shelx_res_checksum              66101
_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 1.846
_oxdiff_exptl_absorpt_empirical_full_min 0.262