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_7055098
_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         'C19 H23 N3 O'
_chemical_formula_sum            'C19 H23 N3 O'
_chemical_formula_weight         309.40
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-07-28
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2015-06-24 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                70.976(10)
_cell_angle_beta                 78.653(12)
_cell_angle_gamma                71.791(15)
_cell_formula_units_Z            2
_cell_length_a                   7.1360(13)
_cell_length_b                   9.7606(13)
_cell_length_c                   13.6208(12)
_cell_measurement_reflns_used    2129
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.8480
_cell_measurement_theta_min      3.8000
_cell_volume                     847.2(2)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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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    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9988
_diffrn_measurement_details
;
  1 omega  -92.00  -48.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  178.0000   30.0000 44

  2 omega  -24.00   23.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000  -90.0000 47

  3 omega  -17.00   24.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000   90.0000 41

  4 omega   32.00   95.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714 -178.0000  -60.0000 63

  5 omega   -7.00   70.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714   38.0000   90.0000 77

  6 omega  -51.00   61.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714  -19.0000 -120.0000 112
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0674991000
_diffrn_orient_matrix_UB_12      0.0697748000
_diffrn_orient_matrix_UB_13      -0.0217288000
_diffrn_orient_matrix_UB_21      -0.0794409000
_diffrn_orient_matrix_UB_22      -0.0342282000
_diffrn_orient_matrix_UB_23      0.0175829000
_diffrn_orient_matrix_UB_31      -0.0143408000
_diffrn_orient_matrix_UB_32      0.0180440000
_diffrn_orient_matrix_UB_33      0.0478239000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0850
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6398
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74206
_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_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0684P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1594
_reflns_number_gt                2632
_reflns_number_total             3619
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5nj02061a3.cif
_cod_data_source_block           3ba
_cod_depositor_comments
'Adding full bibliography for 7055098--7055106.cif.'
_cod_database_code               7055098
_chemical_oxdiff_formula         'C19 H23 N3 O'
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32