Zinc(II)-Mediated Nitrile-Amidoxime Coupling Gives New Insights into H(+)-Assisted Generation of 1,2,4-Oxadiazoles.
Bolotin, Dmitrii S.; Kulish, Kirill I.; Bokach, Nadezhda A.; Starova, Galina L.; Gurzhiy, Vladislav V.; Kukushkin, Vadim Yu; Inorganic chemistry 53 (2014) 10312–10324; doi:10.1021/ic501333s

data_4341092
_publ_section_title
;
 Zinc(II)-Mediated Nitrile-Amidoxime Coupling Gives New Insights into
 H(+)-Assisted Generation of 1,2,4-Oxadiazoles.
;
_journal_issue                   19
_journal_name_full               'Inorganic chemistry'
_journal_page_first              10312
_journal_page_last               10324
_journal_paper_doi               10.1021/ic501333s
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         '2(C7 H7 O3 S), 2(C12 H17 N4 O2)'
_chemical_formula_sum            'C38 H48 N8 O10 S2'
_chemical_formula_weight         840.96
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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     direct
_audit_creation_date             2014-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                87.538(7)
_cell_angle_beta                 86.488(8)
_cell_angle_gamma                67.847(10)
_cell_formula_units_Z            1
_cell_length_a                   8.2774(9)
_cell_length_b                   8.7480(8)
_cell_length_c                   14.9786(10)
_cell_measurement_reflns_used    1731
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.8890
_cell_measurement_theta_min      2.6547
_cell_volume                     1002.43(17)
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_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_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0822619000
_diffrn_orient_matrix_UB_12      0.0061219000
_diffrn_orient_matrix_UB_13      -0.0099519000
_diffrn_orient_matrix_UB_21      -0.0424049000
_diffrn_orient_matrix_UB_22      0.0805809000
_diffrn_orient_matrix_UB_23      -0.0182085000
_diffrn_orient_matrix_UB_31      -0.0039261000
_diffrn_orient_matrix_UB_32      0.0337164000
_diffrn_orient_matrix_UB_33      0.0426771000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1040
_diffrn_reflns_av_unetI/netI     0.2239
_diffrn_reflns_Laue_measured_fraction_full 0.922
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12940
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.499
_diffrn_reflns_theta_min         2.660
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90847
_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            'translucent colorless'
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             445
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     14
_refine_ls_number_reflns         6617
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.1774
_refine_ls_R_factor_gt           0.0835
_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^)+(0.0340P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.2058
_reflns_Friedel_coverage         0.981
_reflns_Friedel_fraction_full    0.904
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3028
_reflns_number_total             6617
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic501333s_si_001.cif
_cod_data_source_block           '[4d](p-TolSO3)'
_cod_depositor_comments
'Adding full bibliography for 4341086--4341092.cif.'
_cod_original_cell_volume        1002.41(17)
_cod_database_code               4341092
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O41-O5
 1.4 with sigma of 0.02
 S1A-C17A = S1A-O5A = S1A-O4A = S1A-O3A = S1A-O41A = S1A-O51A = S1A-O31A
 1.45 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O31) = Uanis(O3) = Uanis(O51) = Uanis(O5) = Uanis(O41) = Uanis(O4)
Uanis(C2) = Uanis(N2) = Uanis(C3) = Uanis(N4)
Uanis(C16A) = Uanis(C15A) = Uanis(C19A) = Uanis(C18A) = Uanis(C17A) =
Uanis(C14A)
Uanis(C8A) = Uanis(C3A) = Uanis(C2A)
Uanis(C9A) = Uanis(C10A) = Uanis(C11A) = Uanis(C12A)
Uanis(O1) = Uanis(N1) = Uanis(C1) = Uanis(N3)
Uanis(C5A) = Uanis(C6A) = Uanis(C7A)
Uanis(C1A) = Uanis(O1A)
Uanis(O31A) = Uanis(O4A) = Uanis(O3A) = Uanis(O51A) = Uanis(O5A) = Uanis(O41A)
Uanis(C12) = Uanis(C9) = Uanis(C10) = Uanis(C11)
Uanis(C4) = Uanis(C5) = Uanis(C6) = Uanis(C7) = Uanis(C8)
Uanis(C17) = Uanis(C14)
4. Others
 Fixed Sof: O3(0.75) O4(0.75) O5(0.75) O31(0.25) O41(0.25) O51(0.25) O3A(0.75)
 O4A(0.75) O5A(0.75) O31A(0.25) O41A(0.25) O51A(0.25)
5.a Everything fixed:
 O1A, O2A, N1A, N2A, N3A, N4A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A,
 C10A, C11A, O1, O2, N1, N2, N3, N4, C1, C2, C3, C4, C5, C12A, C13, C14, C15,
 C16, C17, C18, C19, O3, O4, O5, O31, O41, O51, C6, C7, C8, C9, C10, C11, C12,
 S1A, C13A, C14A, C15A, C16A, C17A, C18A, C19A, O3A, O4A, O5A, O31A, O41A, O51A
5.b Rotating group:
 N1A(H1AA,H1AB), N4A(H4AA,H4AB)
5.c Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C10A(H10A,H10B), C11A(H11A,H11B), C12A(H12A,H12B), C9(H9A,
 H9B), C10(H10C,H10D), C11(H11C,H11D), C12(H12C,H12D)
5.d Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C4(H4), C5(H5), C15(H15),
 C16(H16), C18(H18), C19(H19), C6(H6), C7(H7), C8(H8), C15A(H15A), C16A(H16A),
 C18A(H18A), C19A(H19A)
5.e X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N4(H4B,H4C)
5.f Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C13A(H13D,H13E,H13F)
;