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_7055948
_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_absolute_configuration unk
_chemical_formula_moiety         'C12 H28 N8 O2 Zn, 2(C F3 O3 S)'
_chemical_formula_sum            'C14 H28 F6 N8 O8 S2 Zn'
_chemical_formula_weight         679.93
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.8415(3)
_cell_length_b                   20.4363(4)
_cell_length_c                   16.1946(3)
_cell_measurement_reflns_used    18157
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.0990
_cell_measurement_theta_min      2.9460
_cell_volume                     5573.82(18)
_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 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -41.00   43.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4031   57.0000 -150.0000 84

  2 omega  -51.00   42.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4031   38.0000   60.0000 93

  3 omega   -8.00   18.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -99.0000   30.0000 26

  4 omega  -12.00   67.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -99.0000  -90.0000 79

  5 omega    2.00   93.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968   77.0000   90.0000 91

  6 omega   36.00   68.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -99.0000   30.0000 32

  7 omega   28.00   94.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968   57.0000  -90.0000 66

  8 omega  -42.00  -11.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -57.0000 -120.0000 31
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0025460000
_diffrn_orient_matrix_UB_12      0.0339023000
_diffrn_orient_matrix_UB_13      0.0090199000
_diffrn_orient_matrix_UB_21      -0.0161837000
_diffrn_orient_matrix_UB_22      0.0074471000
_diffrn_orient_matrix_UB_23      -0.0393331000
_diffrn_orient_matrix_UB_31      -0.0387787000
_diffrn_orient_matrix_UB_32      -0.0008532000
_diffrn_orient_matrix_UB_33      0.0170333000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            53585
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.649
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58917
_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    1.621
_exptl_crystal_description       prism
_exptl_crystal_F_000             2784
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.272
_refine_diff_density_min         -1.113
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 4847 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     721
_refine_ls_number_reflns         12565
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0457P)^2^+7.9853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1023
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                11402
_reflns_number_total             12565
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6nj03508f2.cif
_cod_data_source_block           4c_OTf2
_cod_depositor_comments
'Adding full bibliography for 7055945--7055952.cif.'
_cod_original_cell_volume        5573.83(17)
_cod_database_code               7055948
_chemical_oxdiff_formula         'Zn C20 S O3'
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9-F12 \\sim C9-F10 \\sim C9-F11
 with sigma of 0.002
 S4-C10 \\sim S4-C9
 with sigma of 0.002
 C10-F8 \\sim C10-F7 \\sim C10-F9
 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(C10) = Uanis(S4) = Uanis(F8) = Uanis(F7) = Uanis(F9) = Uanis(C9) =
Uanis(F10) = Uanis(F11) = Uanis(F12)
Uanis(C5C) = Uanis(C7C) = Uanis(C1C)
4. Rigid body (RIGU) restrains
 C8C, C7C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.008
 C6C, C5C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.008
5. Others
 Sof(F12)=Sof(C9)=Sof(F11)=Sof(F10)=Sof(O11)=1-FVAR(1)
 Sof(F9)=Sof(O10)=Sof(F8)=Sof(F7)=Sof(C10)=FVAR(1)
 Sof(C6C)=Sof(H6CA)=Sof(H6CB)=Sof(H6CC)=Sof(C5C)=Sof(H5CA)=Sof(H5CB)=1-FVAR(2)
 Sof(C7C)=Sof(H7CA)=Sof(H7CB)=Sof(C8C)=Sof(H8CA)=Sof(H8CB)=Sof(H8CC)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C5A(H5AA,H5AB), C5(H5A,H5B), C5B(H5BA,H5BB), C7C(H7CA,H7CB), C5C(H5CA,H5CB)
6.b Aromatic/amide H refined with riding coordinates:
 N3A(H3A), N3B(H3B), N3(H3), N3C(H3C)
6.c X=CH2 refined with riding coordinates:
 N2A(H2AA,H2AB), N2(H2A,H2B), N2C(H2CA,H2CB), N2B(H2BA,H2BB)
6.d Idealised Me refined as rotating group:
 C3C(H3CA,H3CB,H3CC), C4A(H4AA,H4AB,H4AC), C3B(H3BA,H3BB,H3BC), C4B(H4BA,H4BB,
 H4BC), C4(H4A,H4B,H4C), C4C(H4CA,H4CB,H4CC), C3A(H3AA,H3AB,H3AC), C6A(H6AA,
 H6AB,H6AC), C3(H3D,H3E,H3F), C6(H6A,H6B,H6C), C6B(H6BA,H6BB,H6BC), C8C(H8CA,
 H8CB,H8CC), C6C(H6CA,H6CB,H6CC)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'