Zinc(ii)-mediated generation of 5-amino substituted 2,3-dihydro-1,2,4-oxadiazoles and their further ZnII-catalyzed and O2-involving transformations
Smirnov, Andrey S.; Yandanova, Ekaterina S.; Bokach, Nadezhda A.; Starova, Galina L.; Gurzhiy, Vladislav V.; Avdontceva, Margarita S.; Zolotarev, Andrey A.; Kukushkin, Vadim Yu.; New J. Chem. 39 (2015) 9330–; doi:10.1039/C5NJ02061A

data_7055101
_publ_section_title
;
 Zinc(ii)-mediated generation of 5-amino substituted
 2,3-dihydro-1,2,4-oxadiazoles and their further ZnII-catalyzed and
 O2-involving transformations
;
_journal_issue                   12
_journal_name_full               'New J. Chem.'
_journal_page_first              9330
_journal_paper_doi               10.1039/C5NJ02061A
_journal_volume                  39
_journal_year                    2015
_chemical_formula_moiety         'C23 H23 N3 O'
_chemical_formula_sum            'C23 H23 N3 O'
_chemical_formula_weight         357.44
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-02
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2015-06-26 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                101.637(6)
_cell_angle_beta                 93.380(6)
_cell_angle_gamma                92.887(7)
_cell_formula_units_Z            2
_cell_length_a                   6.1591(5)
_cell_length_b                   12.0853(10)
_cell_length_c                   12.7889(9)
_cell_measurement_reflns_used    2156
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.4250
_cell_measurement_theta_min      3.4340
_cell_volume                     928.86(13)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9992
_diffrn_measurement_details
;
  1 omega  -55.00  -28.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339  101.0000  105.0000 27

  2 omega  -11.00   24.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339 -101.0000    1.0000 35

  3 omega  -11.00   48.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714 -101.0000    1.0000 59

  4 omega   23.00   51.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339   57.0000    0.0000 28

  5 omega  -87.00    3.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339  -57.0000 -150.0000 90

  6 omega  -90.00    1.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339  -38.0000   90.0000 91

  7 omega   16.00   67.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714   38.0000  120.0000 51

  8 omega  -13.00   12.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339  -99.0000   90.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0904563000
_diffrn_orient_matrix_UB_12      0.0293494000
_diffrn_orient_matrix_UB_13      0.0326041000
_diffrn_orient_matrix_UB_21      -0.0320992000
_diffrn_orient_matrix_UB_22      -0.0242502000
_diffrn_orient_matrix_UB_23      0.0432334000
_diffrn_orient_matrix_UB_31      0.0644238000
_diffrn_orient_matrix_UB_32      -0.0464319000
_diffrn_orient_matrix_UB_33      -0.0170414000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7545
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.60
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74191
_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            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1019P)^2^+0.0576P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1728
_reflns_number_gt                3285
_reflns_number_total             4080
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5nj02061a3.cif
_cod_data_source_block           sas210
_cod_depositor_comments
'Adding full bibliography for 7055098--7055106.cif.'
_cod_original_cell_volume        928.85(13)
_cod_database_code               7055101
_chemical_oxdiff_formula         'C23 H23 N3 O1'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32