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_7055100
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-06-27
_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                92.583(4)
_cell_angle_beta                 92.986(4)
_cell_angle_gamma                104.621(4)
_cell_formula_units_Z            2
_cell_length_a                   8.8129(4)
_cell_length_b                   9.0613(5)
_cell_length_c                   16.1691(7)
_cell_measurement_reflns_used    4977
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0140
_cell_measurement_theta_min      5.0560
_cell_volume                     1245.43(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
;
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 10.3829
_diffrn_measured_fraction_theta_full 0.9689
_diffrn_measured_fraction_theta_max 0.9689
_diffrn_measurement_details
;
  1 omega -104.00  -33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   30.0000 71

  2 omega  -74.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   77.0000  150.0000 111

  3 omega    7.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000   90.0000 29

  4 omega -112.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000  -60.0000 101

  5 omega    4.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000 -120.0000 78

  6 omega   64.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  -60.0000 26

  7 omega   87.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000   60.0000 62

  8 omega   77.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -20.0000 -113.6517 26

  9 omega   42.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 50

 10 omega  133.00  159.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 26

 11 omega   79.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 26

 12 omega   86.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 28

 13 omega  151.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  -60.0000 26

 14 omega   55.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 35

 15 omega   52.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000   60.0000 26

 16 omega   87.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 25

 17 omega  116.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 33

 18 omega   87.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 26

 19 omega  140.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 37

 20 omega   65.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 81

 21 omega  105.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 25

 22 omega  153.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 25

 23 omega   84.00  169.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 85

 24 omega  116.00  142.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  120.0000 26

 25 omega   35.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 48

 26 omega   39.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 59

 27 omega   29.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 59

 28 omega  118.00  143.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -60.0000 25

 29 omega   35.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 33

 30 omega   73.00  101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -60.0000 28

 31 omega   37.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 47

 32 omega   67.00   95.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -59.0000  -56.0000 28

 33 omega  131.00  156.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -20.0000 -113.6517 25

 34 omega   60.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 39

 35 omega   50.00  144.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -64.0000   61.9156 94

 36 omega   88.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 23
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1073576000
_diffrn_orient_matrix_UB_12      -0.0417653000
_diffrn_orient_matrix_UB_13      -0.0644804000
_diffrn_orient_matrix_UB_21      0.0630790000
_diffrn_orient_matrix_UB_22      0.1704037000
_diffrn_orient_matrix_UB_23      -0.0156126000
_diffrn_orient_matrix_UB_31      0.1314315000
_diffrn_orient_matrix_UB_32      0.0142573000
_diffrn_orient_matrix_UB_33      0.0688067000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11464
_diffrn_reflns_theta_full        72.50
_diffrn_reflns_theta_max         72.50
_diffrn_reflns_theta_min         5.05
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.492
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85802
_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    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tables
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.929
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+0.5339P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0895
_reflns_number_gt                4211
_reflns_number_total             4826
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5nj02061a3.cif
_cod_data_source_block           sas169
_cod_depositor_comments
'Adding full bibliography for 7055098--7055106.cif.'
_cod_original_cell_volume        1245.42(10)
_cod_database_code               7055100
_chemical_oxdiff_formula         'C32 H24 br1 n3 o1'
_reflns_odcompleteness_completeness 92.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95