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_7055947
_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         'C22 H32 Cl2 N8 O3 Zn, 2(C F3 O3 S)'
_chemical_formula_sum            'C24 H32 Cl2 F6 N8 O9 S2 Zn'
_chemical_formula_weight         890.96
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_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                108.023(4)
_cell_angle_beta                 90.814(4)
_cell_angle_gamma                95.484(4)
_cell_formula_units_Z            2
_cell_length_a                   8.7052(5)
_cell_length_b                   12.9506(6)
_cell_length_c                   17.0474(7)
_cell_measurement_reflns_used    6106
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.9120
_cell_measurement_theta_min      3.1740
_cell_volume                     1817.27(16)
_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
;
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  -99.00  -72.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.4031  178.0000  -60.0000 27

  2 omega  -77.00  -36.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.4031  119.0000   66.0000 41

  3 omega   35.00   92.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4968  178.0000  -90.0000 57

  4 omega   -7.00   78.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4968 -119.0000  -18.0000 85

  5 omega    5.00   91.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4968   77.0000 -120.0000 86

  6 omega   10.00   97.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4968   38.0000  150.0000 87

  7 omega    5.00   96.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4968   38.0000   60.0000 91
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0256047000
_diffrn_orient_matrix_UB_12      0.0352617000
_diffrn_orient_matrix_UB_13      0.0398010000
_diffrn_orient_matrix_UB_21      -0.0248913000
_diffrn_orient_matrix_UB_22      -0.0415946000
_diffrn_orient_matrix_UB_23      0.0173752000
_diffrn_orient_matrix_UB_31      0.0737519000
_diffrn_orient_matrix_UB_32      -0.0195155000
_diffrn_orient_matrix_UB_33      -0.0057031000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16514
_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         2.616
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.027
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85032
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_description       prism
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.589
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         8351
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+4.4074P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1342
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6629
_reflns_number_total             8351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6nj03508f2.cif
_cod_data_source_block           4b_OTf2
_cod_depositor_comments
'Adding full bibliography for 7055945--7055952.cif.'
_cod_database_code               7055947
_chemical_oxdiff_formula         'Zn S F3 C22 H21 N O3'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H3AA,H3AB,H3AC} of C3A, {H4A,H4B,H4C} of C4, All C(H,H)
  groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, {H12A,H12B,H12C} of C12, {H4AA,H4AB,H4AC} of C4A, {H3B,H3C,
  H3D} of C3
2. Restrained distances
 O2-H2
 0.85 with sigma of 0.01
 C11-H2
 1.897194 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N3A(H3A), C8(H8), C9(H9), C10(H10), C7A(H7A), C7(H7), C10A(H10A),
 C9A(H9A), C8A(H8A)
3.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N2A(H2AA,H2AB)
3.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C3A(H3AA,H3AB,H3AC), C3(H3B,H3C,H3D), C4A(H4AA,H4AB,H4AC),
 C12(H12A,H12B,H12C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'