Tuning chemoselectivity in O-/N-arylation of 3-aryl-1,2,4-oxadiazolones with ortho-(trimethylsilyl)phenyl triflates via aryne insertion.
Zhou, Lijing; Li, Hongji; Zhang, Wenge; Wang, Lei; Chemical communications (Cambridge, England) 54 (2018) 4822–4825; doi:10.1039/c8cc00124c

data_7121562
_publ_section_title
;
 Tuning chemoselectivity in O-/N-arylation of 3-aryl-1,2,4-oxadiazolones
 with ortho-(trimethylsilyl)phenyl triflates via aryne insertion.
;
_journal_issue                   38
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4822
_journal_page_last               4825
_journal_paper_doi               10.1039/c8cc00124c
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C14 H10 N2 O2'
_chemical_formula_weight         238.24
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-12-25 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.41(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.660(3)
_cell_length_b                   5.7506(12)
_cell_length_c                   14.623(3)
_cell_measurement_temperature    289(2)
_cell_volume                     1162.7(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      289(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20614
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_correction_T_min  0.9834
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.2017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1107
_reflns_number_gt                2177
_reflns_number_total             2674
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc00124c2.cif
_cod_data_source_block           t
_cod_depositor_comments
;
          Adding full bibliography for 7121562.cif.

2025-03-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1162.7(4)
_cod_original_formula_sum        'C28 H20 N4 O4'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     476.48
_cod_database_code               7121562