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_7055103
_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         'C22 H21 N3 O'
_chemical_formula_sum            'C22 H21 N3 O'
_chemical_formula_weight         343.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-07-01
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2015-07-02 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.242(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1527(8)
_cell_length_b                   10.0852(7)
_cell_length_c                   10.4387(9)
_cell_measurement_reflns_used    2441
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.9610
_cell_measurement_theta_min      5.1360
_cell_volume                     904.05(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
;
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
;
_diffrn_ambient_temperature      100.00(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.9857
_diffrn_measurement_details
;
  1 omega  -46.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000   30.0000 79

  2 omega  -73.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   77.0000  -90.0000 108

  3 omega   60.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -60.0000 27

  4 omega   66.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -180.0000 44

  5 omega   36.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  120.0000 29

  6 omega   32.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 33

  7 omega   40.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 52

  8 omega   39.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 54

  9 omega  152.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -60.0000 25

 10 omega   39.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 52

 11 omega   66.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   30.0000 27

 12 omega   72.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  120.0000 37

 13 omega  152.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -150.0000 25

 14 omega   71.00  101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 30

 15 omega  151.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 25

 16 omega   86.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 29

 17 omega   46.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 45

 18 omega  118.00  145.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -60.0000 27

 19 omega  152.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -60.0000 25

 20 omega   36.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 53

 21 omega   77.00  131.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -180.0000 54

 22 omega   40.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -33.0000  156.0000 25

 23 omega   40.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 25

 24 omega  108.00  135.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -60.0000 27

 25 omega  149.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   30.0000 27

 26 omega  137.00  167.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -120.0000 30

 27 omega -109.00  -50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000  -30.0000 59

 28 omega -118.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -77.0000   60.0000 106

 29 omega   58.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -180.0000 27

 30 omega   11.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   57.0000   30.0000 28

 31 omega   85.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 27

 32 omega   80.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 25

 33 omega  117.00  144.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -14.0000 -120.9673 27

 34 omega  144.00  169.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 25

 35 omega  127.00  162.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 35

 36 omega   80.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 27

 37 omega  153.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 25

 38 omega   83.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 27

 39 omega   85.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1058910000
_diffrn_orient_matrix_UB_12      -0.0362917000
_diffrn_orient_matrix_UB_13      -0.0817394000
_diffrn_orient_matrix_UB_21      0.1238711000
_diffrn_orient_matrix_UB_22      -0.0529438000
_diffrn_orient_matrix_UB_23      0.1313131000
_diffrn_orient_matrix_UB_31      -0.0750040000
_diffrn_orient_matrix_UB_32      -0.1385858000
_diffrn_orient_matrix_UB_33      -0.0288264000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7495
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.482
_diffrn_reflns_theta_min         4.515
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68670
_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    1.262
_exptl_crystal_description       prism
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1044 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3270
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0453P)^2^+0.0714P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.842
_reflns_Friedel_fraction_max     0.815
_reflns_number_gt                2797
_reflns_number_total             3270
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5nj02061a3.cif
_cod_data_source_block           sas98_2
_cod_depositor_comments
'Adding full bibliography for 7055098--7055106.cif.'
_cod_original_cell_volume        904.06(14)
_cod_database_code               7055103
_chemical_oxdiff_formula         'C22 H21 N3 O1'
_reflns_odcompleteness_completeness 94.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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:
 C17(H17), C15(H15), C21(H21), C9(H9), C22(H22), C18(H18), C11(H11), C19(H19),
 C10(H10), C16(H16), C23(H23), C14(H14), C13(H13), C20(H20), C12(H12)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_res_checksum              95101
_shelxl_version_number           2014/6