Organocatalytic Synthesis of Fused Bicyclic 2,3-Dihydro-1,3,4-oxadiazoles through an Intramolecular Cascade Cyclization.
Fugard, Alison J.; Thompson, Bethany K.; Slawin, Alexandra M. Z.; Taylor, James E.; Smith, Andrew D.; Organic letters 17 (2015) 5824–5827; doi:10.1021/acs.orglett.5b02997

data_1540569
_publ_section_title
;
 Organocatalytic Synthesis of Fused Bicyclic 2,3-Dihydro-1,3,4-oxadiazoles
 through an Intramolecular Cascade Cyclization.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5824
_journal_page_last               5827
_journal_paper_doi               10.1021/acs.orglett.5b02997
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C17 H11 F3 N2 O3'
_chemical_formula_sum            'C17 H11 F3 N2 O3'
_chemical_formula_weight         348.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.446(8)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   13.835(3)
_cell_length_b                   14.066(2)
_cell_length_c                   7.7299(13)
_cell_measurement_reflns_used    1986
_cell_measurement_temperature    125
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      24.46
_cell_volume                     1491.6(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      125
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            14381
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.358
_diffrn_reflns_theta_min         4.502
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.152
_exptl_absorpt_correction_T_max  0.794
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.28
_refine_ls_extinction_coef       0.0177(11)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.5799P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                2645
_reflns_number_total             2722
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol5b02997_si_002.cif
_cod_data_source_block           20
_cod_depositor_comments          'Adding full bibliography for 1540569.cif.'
_cod_original_cell_volume        1491.5(5)
_cod_database_code               1540569