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_7055106
_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         'C32 H24 Br N3 O'
_chemical_formula_sum            'C32 H24 Br N3 O'
_chemical_formula_weight         546.45
_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   mixed
_audit_creation_date             2014-09-19
_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                83.343(4)
_cell_angle_beta                 69.786(5)
_cell_angle_gamma                61.160(5)
_cell_formula_units_Z            2
_cell_length_a                   10.5963(6)
_cell_length_b                   10.8613(5)
_cell_length_c                   13.9872(6)
_cell_measurement_reflns_used    16732
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      76.0010
_cell_measurement_theta_min      4.6270
_cell_volume                     1320.75(14)
_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      290(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -87.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   19.0000   60.0000 127

  2 omega  -11.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000   90.0000 33

  3 omega  -37.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -60.0000 63

  4 omega   72.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000  120.0000 57

  5 omega   57.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -120.0000 52

  6 omega   64.00  124.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -60.0000 60

  7 omega   97.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -80.0000 -141.5526 49

  8 omega   45.00   76.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -80.0000 -141.5526 31

  9 omega   55.00   81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -80.0000   -5.9403 26

 10 omega   90.00  128.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -20.0000 -177.0453 38

 11 omega  109.00  141.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   60.0000 32

 12 omega   89.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -120.0000 59

 13 omega   36.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 52

 14 omega   38.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 54

 15 omega   58.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -20.0000 -177.0453 26

 16 omega   70.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -66.0000   28.6581 30

 17 omega   39.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 51

 18 omega   39.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 57

 19 omega   59.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 26

 20 omega   31.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  -60.0000 142

 21 omega   38.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 49

 22 omega   39.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   60.0000 49

 23 omega  120.00  160.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   -8.0000   99.5787 40

 24 omega   88.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 25

 25 omega   83.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 25

 26 omega   36.00   79.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 43

 27 omega   93.00  119.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 26

 28 omega  142.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 33

 29 omega   95.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 26

 30 omega   43.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 55

 31 omega   88.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 27

 32 omega   43.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 67

 33 omega  124.00  160.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 36

 34 omega   83.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -150.0000 46

 35 omega   36.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   -8.0000   99.5787 72

 36 omega   72.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   60.0000 25

 37 omega  103.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -80.0000   -5.9403 26

 38 omega  104.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -180.0000 25

 39 omega   99.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -72.0000  135.1193 47

 40 omega   48.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 66

 41 omega   95.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -60.0000 25

 42 omega  125.00  150.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 25

 43 omega   40.00   66.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 26

 44 omega   89.00  122.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   60.0000 33

 45 omega   58.00  119.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -121.0000  -65.7468 61

 46 omega  -99.00  -73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -73.0000  -91.0000 26

 47 omega  -40.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000    0.0000 29

 48 omega -112.00  -55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000    0.0000 57

 49 omega  -58.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -73.0000  -91.0000 48

 50 omega   21.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   38.0000   90.0000 51

 51 omega    6.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   89.0000   80.2486 25

 52 omega   17.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   81.0000 -123.4900 25

 53 omega   18.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   79.0000  -15.0215 25

 54 omega   18.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   80.0000   36.2881 26

 55 omega   17.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   81.0000  -71.9030 26

 56 omega   22.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000  143.7452 25

 57 omega   29.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   77.0000  168.0786 26

 58 omega   32.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000  -83.2688 75

 59 omega   31.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000   98.8919 31

 60 omega   36.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   69.0000  -25.0979 27

 61 omega   35.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000  -18.2266 26

 62 omega   34.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000 -168.7121 26

 63 omega   34.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   43.8619 26

 64 omega   37.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000 -117.9934 26

 65 omega   49.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   66.0000  128.4412 26

 66 omega   51.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   77.0000   -6.0322 26

 67 omega  106.00  132.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   77.0000   -6.0322 26

 68 omega   53.00  122.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   67.0000  -46.0114 69

 69 omega   55.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   58.0000 -110.1536 27

 70 omega   55.00   81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   60.0000  159.5952 26

 71 omega   59.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   61.0000   69.2614 25

 72 omega   58.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   65.0000   28.6086 26

 73 omega   65.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   73.0000 -176.4796 26

 74 omega   68.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   70.0000  158.1785 26

 75 omega   79.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 28

 76 omega   79.00  152.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 73

 77 omega  111.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 26

 78 omega  134.00  160.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -90.0000 26

 79 omega   79.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 31

 80 omega   85.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -150.0000 36

 81 omega   83.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   62.0000 -116.4085 31

 82 omega   80.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -60.0000 33

 83 omega   79.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -90.0000 47

 84 omega  117.00  144.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 27

 85 omega   84.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 62

 86 omega   79.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 32

 87 omega   79.00  135.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 56

 88 omega   90.00  136.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 46

 89 omega   79.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 38

 90 omega   79.00  134.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 55

 91 omega   84.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 25

 92 omega  118.00  154.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 36

 93 omega   79.00  140.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 61

 94 omega   81.00  133.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 52

 95 omega   86.00  136.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 50

 96 omega  125.00  151.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 26

 97 omega   84.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 25

 98 omega  122.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 26

 99 omega   79.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 26

100 omega  113.00  139.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 26

101 omega   83.00  119.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -30.0000 36
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0664521000
_diffrn_orient_matrix_UB_12      0.0669489000
_diffrn_orient_matrix_UB_13      -0.0863468000
_diffrn_orient_matrix_UB_21      -0.1148378000
_diffrn_orient_matrix_UB_22      -0.0577389000
_diffrn_orient_matrix_UB_23      0.0409388000
_diffrn_orient_matrix_UB_31      -0.1156540000
_diffrn_orient_matrix_UB_32      0.1360270000
_diffrn_orient_matrix_UB_33      0.0685321000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31953
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.494
_diffrn_reflns_theta_min         3.374
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.350
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69498
_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    1.374
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5224
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0844P)^2^+0.5611P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1386
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4739
_reflns_number_total             5224
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5nj02061a3.cif
_cod_data_source_block           6ed
_cod_depositor_comments
'Adding full bibliography for 7055098--7055106.cif.'
_cod_original_cell_volume        1320.74(13)
_cod_database_code               7055106
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 94.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1-H1
 0.9 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
;