Ozonolysis of Bicyclic 1,2-Dioxines: Initial Scope and Mechanistic Insights
Nicole M. Cain; Edward R. T. Tiekink; Dennis K. Taylor; Journal of Organic Chemistry 77 (2012) 3808–3819; doi:10.1021/jo3001518

data_4027154
_publ_contact_author_address
;
    School of Materials Science and Engineering, 
    Nanyang Technological University,  
    Singapore 639798
;
_publ_contact_author_email
;
Edward.Tiekink@gmail.com
;
_publ_contact_author_fax         ' (65) 6790 9801 '
_publ_contact_author_name        ' Edward RT Tiekink '
_publ_contact_author_phone       ' (65) 6790 6402 '
_publ_section_title
;
 Ozonolysis of Bicyclic 1,2-Dioxines: Initial Scope and Mechanistic
 Insights
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3808
_journal_page_last               3819
_journal_paper_doi               10.1021/jo3001518
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C11 H18 O5'
_chemical_formula_sum            'C11 H18 O5'
_chemical_formula_weight         230.25
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90
_cell_angle_beta                 107.784(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.686(3)
_cell_length_b                   7.0118(19)
_cell_length_c                   16.046(5)
_cell_measurement_reflns_used    4315
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      40.3
_cell_measurement_theta_min      2.7
_cell_volume                     1144.8(6)
_computing_cell_refinement       CrystalClear
_computing_data_collection
'CrystalClear (Rigaku Americas Corporation, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) & Brandenburg (Crystal Impact, 2006)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      98(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  AFC12\K/SATURN724
_diffrn_measurement_method       \w
_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  0.022
_diffrn_reflns_av_sigmaI/netI    0.028
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4763
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         2.7
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.30
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.047
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.053P)^2^+0.7483P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.112
_refine_ls_wR_factor_ref         0.115
_reflns_number_gt                2203
_reflns_number_total             2352
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo3001518_si_002.cif
_cod_data_source_block           R44
_cod_original_cell_volume        1144.9(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4027154