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_7055951
_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 H22 N4 O6 Zn'
_chemical_formula_sum            'C18 H22 N4 O6 Zn'
_chemical_formula_weight         455.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 139.46(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.955(2)
_cell_length_b                   17.5685(11)
_cell_length_c                   15.782(3)
_cell_measurement_reflns_used    11136
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.2832
_cell_measurement_theta_min      2.6062
_cell_volume                     2154.5(18)
_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 0.999
_diffrn_measurement_details
;
  1 omega  -61.00  -35.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4081 -178.0000   90.0000 26

  2 omega  -90.00   -2.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4081  -57.0000  -30.0000 88

  3 omega  -55.00   51.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4081   19.0000  150.0000 106

  4 omega   32.00   70.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3456 -178.0000  -60.0000 38

  5 omega   21.00   62.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3456  -99.0000  120.0000 41

  6 omega   -7.00   20.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3456   77.0000    0.0000 27

  7 omega   62.00   92.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3456   77.0000 -150.0000 30

  8 omega    0.00   37.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3456   77.0000 -150.0000 37

  9 omega    8.00   53.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3456  -99.0000  -90.0000 45

 10 omega    3.00   38.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4081   77.0000 -150.0000 35

 11 omega  -73.00   -1.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4081  -57.0000 -150.0000 72

 12 omega  -83.00  -21.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4081  -57.0000   60.0000 62

 13 omega  -87.00   44.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4081    0.0000   60.0000 131

 14 omega  -52.00  -14.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4081   77.0000 -150.0000 38

 15 omega    0.00   58.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3456   77.0000  120.0000 58

 16 omega    7.00   65.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3456  -99.0000    0.0000 58
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0739782000
_diffrn_orient_matrix_UB_12      0.0097946000
_diffrn_orient_matrix_UB_13      -0.0185482000
_diffrn_orient_matrix_UB_21      0.0243598000
_diffrn_orient_matrix_UB_22      -0.0266340000
_diffrn_orient_matrix_UB_23      0.0455857000
_diffrn_orient_matrix_UB_31      0.0477137000
_diffrn_orient_matrix_UB_32      0.0287146000
_diffrn_orient_matrix_UB_33      0.0485754000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            37536
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.611
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75560
_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    1.405
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0291P)^2^+1.4642P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0748
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4210
_reflns_number_total             4962
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6nj03508f2.cif
_cod_data_source_block           2a
_cod_depositor_comments
'Adding full bibliography for 7055945--7055952.cif.'
_cod_original_cell_volume        2154.3(14)
_cod_database_code               7055951
_chemical_oxdiff_formula         'Zn N4 O6 C18 H18'
_reflns_odcompleteness_completeness 99.89
_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), C3(H3), C3A(H3A), C7(H7), C4(H4), C6A(H6A), C5A(H5A), C4A(H4A),
 C6(H6), C5(H5)
2.b X=CH2 refined with riding coordinates:
 N2A(H2AA,H2AB), N2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C9A(H9AA,H9AB,H9AC), C9(H9A,H9B,H9C)
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'