Trinuclear (aminonitrone)ZnII complexes as key intermediates in zinc(ii)-mediated generation of 1,2,4-oxadiazoles from amidoximes and nitriles
Bolotin, Dmitrii S.; Il'in, Mikhail V.; Novikov, Alexander S.; Bokach, Nadezhda A.; Suslonov, Vitalii V.; Kukushkin, Vadim Yu.; New J. Chem. 41 (2017) 1940–; doi:10.1039/C6NJ03508F

data_7055946
_publ_section_title
;
 Trinuclear (aminonitrone)ZnII complexes as key intermediates in
 zinc(ii)-mediated generation of 1,2,4-oxadiazoles from amidoximes and
 nitriles
;
_journal_issue                   5
_journal_name_full               'New J. Chem.'
_journal_page_first              1940
_journal_paper_doi               10.1039/C6NJ03508F
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C18 H20 Cl2 N4 O6 Zn'
_chemical_formula_sum            'C18 H20 Cl2 N4 O6 Zn'
_chemical_formula_weight         524.65
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_audit_update_record
;
2016-09-12 deposited with the CCDC.
2017-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.305(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.7550(17)
_cell_length_b                   10.5714(5)
_cell_length_c                   13.5063(6)
_cell_measurement_reflns_used    5486
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.0849
_cell_measurement_theta_min      2.7289
_cell_volume                     4386.2(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -91.00  -65.00   1.0000    8.1200
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -57.0000 -150.0000 26

  2 omega  -98.00  -32.00   1.0000    8.1200
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  178.0000  -30.0000 66

  3 omega  -60.00   51.00   1.0000    8.1200
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   19.0000   30.0000 111

  4 omega   -5.00   36.00   1.0000    8.1200
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -106.0000  163.0000 41

  5 omega   -7.00   93.00   1.0000    8.1200
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000 -120.0000 100

  6 omega  -25.00    3.00   1.0000    8.1200
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  120.0000 28

  7 omega   36.00   65.00   1.0000    8.1200
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  120.0000 29

  8 omega   26.00   51.00   1.0000    8.1200
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -106.0000  -16.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0165245000
_diffrn_orient_matrix_UB_12      0.0084588000
_diffrn_orient_matrix_UB_13      0.0384835000
_diffrn_orient_matrix_UB_21      0.0676275000
_diffrn_orient_matrix_UB_22      -0.0024905000
_diffrn_orient_matrix_UB_23      0.0228535000
_diffrn_orient_matrix_UB_31      0.0136878000
_diffrn_orient_matrix_UB_32      0.0552969000
_diffrn_orient_matrix_UB_33      0.0113675000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18244
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.735
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.406
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_description       prism
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.535
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0406P)^2^+16.9329P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1039
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4459
_reflns_number_total             5042
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6nj03508f2.cif
_cod_data_source_block           2b
_cod_depositor_comments
'Adding full bibliography for 7055945--7055952.cif.'
_cod_database_code               7055946
_chemical_oxdiff_formula         'Zn Cl2 N4 C18'
_reflns_odcompleteness_completeness 99.11
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C4A(H4A), C6A(H6A), C6(H6), C4(H4), C7(H7), C5A(H5A), C5(H5)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N2A(H2AA,H2AB)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C9A(H9AA,H9AB,H9AC)
2.d Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1(H1)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'