Ground-State Dioxygen Undergoes Metal-Free [3+2]-Annulations with Allenes and Nitrosoarenes Under Ambient Conditions
Liu, Rai-Shung; Liu, Jinxian; Skaria, Manisha; Sharma, Pankaj; Chiang, Yun-Wei; Chem. Sci.  (2017) –; doi:10.1039/C7SC01770G

data_1546111
_publ_section_title
;
 Ground-State Dioxygen Undergoes Metal-Free [3+2]-Annulations with Allenes
 and Nitrosoarenes Under Ambient Conditions
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC01770G
_journal_year                    2017
_chemical_formula_moiety         'C17 H17 N O4'
_chemical_formula_sum            'C17 H17 N O4'
_chemical_formula_weight         299.32
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-09-30 deposited with the CCDC.
2017-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.20(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.480(7)
_cell_length_b                   5.698(4)
_cell_length_c                   15.656(13)
_cell_measurement_reflns_used    901
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      19.36
_cell_measurement_theta_min      2.67
_cell_volume                     755.3(10)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.915
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  'Bruker APEX2'
_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  0.3365
_diffrn_reflns_av_sigmaI/netI    0.2626
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4585
_diffrn_reflns_theta_full        25.21
_diffrn_reflns_theta_max         25.21
_diffrn_reflns_theta_min         1.30
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_correction_T_min  0.9117
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.130
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(9)
_refine_ls_extinction_coef       0.08(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2196
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.215
_refine_ls_R_factor_all          0.2549
_refine_ls_R_factor_gt           0.1803
_refine_ls_shift/su_max          0.071
_refine_ls_shift/su_mean         0.015
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4062
_refine_ls_wR_factor_ref         0.4474
_reflns_number_gt                1103
_reflns_number_total             2196
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7sc01770g2.cif
_cod_data_source_block           a18125
_cod_original_cell_volume        755.3(11)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1546111