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_1546110
_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         'C28 H24 Cl2 N2 O2'
_chemical_formula_sum            'C28 H24 Cl2 N2 O2'
_chemical_formula_weight         491.39
_chemical_name_systematic
;
 ?
;
_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
;
2017-03-27 deposited with the CCDC.
2017-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.487(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.420(2)
_cell_length_b                   5.9044(8)
_cell_length_c                   25.212(3)
_cell_measurement_reflns_used    9546
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.05
_cell_measurement_theta_min      2.48
_cell_volume                     2444.2(5)
_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    'SIR97 (Giacovazzo et al, 1997)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'D8 Venture'
_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  0.0853
_diffrn_reflns_av_sigmaI/netI    0.0773
_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       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            38821
_diffrn_reflns_theta_full        25.46
_diffrn_reflns_theta_max         25.46
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  0.9971
_exptl_absorpt_correction_T_min  0.9196
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.985
_refine_diff_density_min         -1.595
_refine_diff_density_rms         0.259
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.629
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         8777
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      2.631
_refine_ls_R_factor_all          0.2885
_refine_ls_R_factor_gt           0.2542
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_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          0.5938
_refine_ls_wR_factor_ref         0.6117
_reflns_number_gt                6451
_reflns_number_total             8777
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7sc01770g2.cif
_cod_data_source_block           d18485f
_cod_original_cell_volume        2444.3(6)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1546110