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_7055104
_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         'C17 H19 N3 O'
_chemical_formula_sum            'C17 H19 N3 O'
_chemical_formula_weight         281.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2015-07-01 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.150(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5535(3)
_cell_length_b                   6.1044(3)
_cell_length_c                   26.1423(10)
_cell_measurement_reflns_used    5745
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.7450
_cell_measurement_theta_min      3.1290
_cell_volume                     1512.72(11)
_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, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -20.00   19.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000 -120.0000 39

  2 omega  -89.00  -56.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  178.0000  150.0000 33

  3 omega  -25.00   22.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000    0.0000 47

  4 omega   -3.00   43.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   57.0000 -180.0000 46

  5 omega  -48.00   -8.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -57.0000  -90.0000 40

  6 omega   38.00   85.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  178.0000   60.0000 47

  7 omega   -2.00   90.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   38.0000 -150.0000 92

  8 omega  -46.00   40.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -57.0000   30.0000 86

  9 omega  -92.00  -21.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  152.0000  102.0000 71

 10 omega  -22.00    5.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -38.0000  -30.0000 27

 11 omega  -73.00  -30.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  121.0000  -57.0000 43

 12 omega  -89.00  -58.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -38.0000  -30.0000 31

 13 omega   -3.00   83.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   57.0000  -60.0000 86

 14 omega   -3.00   88.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   57.0000   60.0000 91

 15 omega  -52.00  -27.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -38.0000  120.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0258359000
_diffrn_orient_matrix_UB_12      0.1081473000
_diffrn_orient_matrix_UB_13      0.0044747000
_diffrn_orient_matrix_UB_21      -0.0022494000
_diffrn_orient_matrix_UB_22      -0.0137736000
_diffrn_orient_matrix_UB_23      0.0268166000
_diffrn_orient_matrix_UB_31      0.0702123000
_diffrn_orient_matrix_UB_32      -0.0402145000
_diffrn_orient_matrix_UB_33      0.0028467000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            23114
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.815
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93905
_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            'translucent colorless'
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0503P)^2^+0.4110P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1247
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2657
_reflns_number_total             3439
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5nj02061a3.cif
_cod_data_source_block           3aa
_cod_depositor_comments
'Adding full bibliography for 7055098--7055106.cif.'
_cod_original_cell_volume        1512.74(10)
_cod_database_code               7055104
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C8(H8A,H8B,H8C)
;