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_7055099
_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         'C26 H20 N2 O'
_chemical_formula_sum            'C26 H20 N2 O'
_chemical_formula_weight         376.44
_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
_audit_creation_date             2015-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-06-24 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                68.395(4)
_cell_angle_beta                 71.217(4)
_cell_angle_gamma                69.263(4)
_cell_formula_units_Z            2
_cell_length_a                   10.2724(4)
_cell_length_b                   10.5468(4)
_cell_length_c                   10.7163(4)
_cell_measurement_reflns_used    9249
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      31.6960
_cell_measurement_theta_min      2.5744
_cell_volume                     984.70(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   59.00   88.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   57.0000  120.0000 29

  2 omega   -7.00   42.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -99.0000 -150.0000 49

  3 omega   15.00   62.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -99.0000    0.0000 47

  4 omega  -17.00   67.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -99.0000   90.0000 84

  5 omega    5.00   95.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   38.0000  -60.0000 90

  6 omega   37.00   67.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -99.0000 -120.0000 30

  7 omega  -48.00   62.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -19.0000  -60.0000 110

  8 omega  -36.00    6.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2661  -77.0000 -120.0000 42

  9 omega  -25.00   45.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2661   57.0000  150.0000 70

 10 omega   -4.00   65.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   77.0000 -180.0000 69

 11 omega   -5.00   74.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   77.0000   90.0000 79

 12 omega  -43.00   42.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -57.0000 -120.0000 85

 13 omega    5.00   94.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   57.0000   30.0000 89
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0278287000
_diffrn_orient_matrix_UB_12      -0.0694468000
_diffrn_orient_matrix_UB_13      0.0403220000
_diffrn_orient_matrix_UB_21      -0.0633737000
_diffrn_orient_matrix_UB_22      -0.0174171000
_diffrn_orient_matrix_UB_23      0.0077427000
_diffrn_orient_matrix_UB_31      0.0306394000
_diffrn_orient_matrix_UB_32      -0.0225729000
_diffrn_orient_matrix_UB_33      -0.0603399000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0209
_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       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17304
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.580
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0423P)^2^+0.3882P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3935
_reflns_number_total             4524
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5nj02061a3.cif
_cod_data_source_block           5e
_cod_depositor_comments
'Adding full bibliography for 7055098--7055106.cif.'
_cod_original_cell_volume        984.70(8)
_cod_database_code               7055099
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C26 H20 N2 O'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
  C23(H23), C24(H24), C25(H25), C26(H26)
;
_olex2_submission_special_instructions 'No special instructions were received'