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_7055102
_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         'C27 H23 N3 O'
_chemical_formula_sum            'C27 H23 N3 O'
_chemical_formula_weight         405.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-06-30 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.188(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.9818(13)
_cell_length_b                   8.6205(3)
_cell_length_c                   23.3388(10)
_cell_measurement_reflns_used    8032
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.5810
_cell_measurement_theta_min      2.9730
_cell_volume                     4217.8(4)
_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)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -12.00   20.25   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000  -90.0000 43

  2 omega  -94.00  -37.00   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777 -178.0000  -90.0000 76

  3 omega   -2.00   80.50   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   57.0000 -150.0000 110

  4 omega   65.00   95.75   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  178.0000  -30.0000 41

  5 omega    3.00   64.50   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   57.0000  120.0000 82

  6 omega  -87.00  -36.00   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777 -178.0000    0.0000 68

  7 omega  -10.00   41.00   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   77.0000    0.0000 68

  8 omega   55.00   81.25   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   77.0000    0.0000 35

  9 omega  -35.00  -21.50   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -57.0000   30.0000 18
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0229836000
_diffrn_orient_matrix_UB_12      0.0237168000
_diffrn_orient_matrix_UB_13      0.0112388000
_diffrn_orient_matrix_UB_21      -0.0152367000
_diffrn_orient_matrix_UB_22      -0.0731655000
_diffrn_orient_matrix_UB_23      -0.0084176000
_diffrn_orient_matrix_UB_31      0.0195466000
_diffrn_orient_matrix_UB_32      -0.0292396000
_diffrn_orient_matrix_UB_33      0.0302361000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            8727
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         2.626
_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  0.70041
_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    1.277
_exptl_crystal_description       prism
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     562
_refine_ls_number_reflns         8727
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0912
_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^)+(0.0521P)^2^+13.8748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2150
_refine_ls_wR_factor_ref         0.2260
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6768
_reflns_number_total             8727
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5nj02061a3.cif
_cod_data_source_block           sas168
_cod_depositor_comments
'Adding full bibliography for 7055098--7055106.cif.'
_cod_database_code               7055102
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C10 N O4 H10'
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.846(3) 0.154(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C18'(H18'), C19'(H19'), C27'(H27'), C28'(H28'), C11'(H11'), C26'(H26'),
 C20'(H20'), C12'(H12'), C16'(H16'), C21'(H21'), C24'(H24'), C25'(H25'),
 C23'(H23'), C8'(H8'), C13'(H13'), C15'(H15'), C9'(H9'), C22'(H22'), C14'(H14'),
  C17'(H17'), C19(H19), C18(H18), C28(H28), C21(H21), C24(H24), C25(H25),
 C26(H26), C22(H22), C27(H27), C8(H8), C23(H23), C20(H20), C13(H13), C11(H11),
 C12(H12), C17(H17), C9(H9), C14(H14), C16(H16), C15(H15)
3.b Idealised Me refined as rotating group:
 C10'(H10A,H10B,H10C), C10(H10D,H10E,H10F)
;
_olex2_submission_special_instructions 'No special instructions were received'