Facile and Selective Procedure for the Synthesis of Bridged 1,2,4,5-Tetraoxanes; Strong Acids As Cosolvents and Catalysts for Addition of Hydrogen Peroxide to β-Diketones
Alexander O. Terent'ev; Dmitry A. Borisov; Vladimir V. Chernyshev; Gennady I. Nikishin; Journal of Organic Chemistry 74 (2009) 3335–3340; doi:10.1021/jo900226b

data_4024504
_publ_contact_author             V.V.Chernyshev
_publ_contact_author_address
;
      Department of Chemistry 
      Moscow State University
      119991 Moscow
      Russia
;
_publ_contact_author_email       vladimir@struct.chem.msu.ru
_publ_contact_author_fax         '+ 7-095-9390898'
_publ_contact_author_name        'Dr. Vladimir V. Chernyshev'
_publ_contact_author_phone       '+ 7-095-9393654'
_publ_section_title
;
Facile and Selective Procedure for the Synthesis of Bridged
1,2,4,5-Tetraoxanes; Strong Acids As Cosolvents and Catalysts for Addition
of Hydrogen Peroxide to \b-Diketones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3335
_journal_page_last               3340
_journal_paper_doi               10.1021/jo900226b
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C8 H11 N O4'
_chemical_formula_sum            'C8 H11 N O4'
_chemical_formula_weight         185.18
_chemical_name_systematic
; 
3-(1,4-Dimethyl-2,3,5,6-tetraoxabicyclo[2.2.1]hept-7-yl)propanenitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.944(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5187(10)
_cell_length_b                   9.6577(15)
_cell_length_c                   17.276(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      36.28
_cell_measurement_theta_min      27.33
_cell_volume                     917.3(3)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1852
_diffrn_reflns_theta_full        69.97
_diffrn_reflns_theta_max         69.97
_diffrn_reflns_theta_min         5.14
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 130
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.922
_exptl_absorpt_correction_T_max  0.8974
_exptl_absorpt_correction_T_min  0.7792
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was   4
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.026
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0409P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                866
_reflns_number_total             1742
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900226b_si_003_2.cif
_cod_data_source_block           ioh19
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4024504