#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:11:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178424 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/45/4024503.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024503
loop_
_publ_author_name
'Alexander O. Terent'ev'
'Dmitry A. Borisov'
'Vladimir V. Chernyshev'
'Gennady I. Nikishin'
_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 β-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         'C13 H16 O4'
_chemical_formula_sum            'C13 H16 O4'
_chemical_formula_weight         236.26
_chemical_name_systematic
; 
1,4-Dimethyl-7-(3-methylbenzyl)-2,3,5,6-tetraoxabicyclo[2.2.1]heptane
;
_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                90.00
_cell_angle_beta                 107.530(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6396(8)
_cell_length_b                   10.8859(11)
_cell_length_c                   11.1091(12)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      35.45
_cell_measurement_theta_min      23.50
_cell_volume                     1226.9(2)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'κ-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  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0541
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2443
_diffrn_reflns_theta_full        69.92
_diffrn_reflns_theta_max         69.92
_diffrn_reflns_theta_min         4.36
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 130
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_correction_T_min  0.853
_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    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0021(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0587
_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/[σ²(Fo²)+(0.0799P)²+0.019P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1749
_reflns_number_gt                1307
_reflns_number_total             2313
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900226b_si_003_1.cif
_cod_data_source_block           ioh10
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024503
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4943(3) 0.1173(3) 0.8350(3) 0.0500(7) Uani 1 1 d . . .
O2 O 0.5437(2) 0.1778(2) 0.74436(19) 0.0617(6) Uani 1 1 d . . .
O3 O 0.6663(2) 0.2393(2) 0.8257(2) 0.0613(6) Uani 1 1 d . . .
C4 C 0.6680(3) 0.2048(3) 0.9503(3) 0.0508(8) Uani 1 1 d . . .
O5 O 0.5792(2) 0.0167(2) 0.8842(2) 0.0630(6) Uani 1 1 d . . .
O6 O 0.7021(2) 0.0780(2) 0.9651(2) 0.0639(7) Uani 1 1 d . . .
C7 C 0.5248(3) 0.2064(3) 0.9441(3) 0.0438(7) Uani 1 1 d . . .
H7 H 0.5115 0.1682 1.0193 0.053 Uiso 1 1 calc . . .
C8 C 0.3596(4) 0.0684(3) 0.7718(3) 0.0680(10) Uani 1 1 d . . .
H8A H 0.3228 0.0361 0.8342 0.102 Uiso 1 1 calc . . .
H8B H 0.3648 0.0043 0.7142 0.102 Uiso 1 1 calc . . .
H8C H 0.3044 0.1334 0.7262 0.102 Uiso 1 1 calc . . .
C9 C 0.7711(3) 0.2768(4) 1.0443(3) 0.0731(11) Uani 1 1 d . . .
H9A H 0.8560 0.2585 1.0350 0.110 Uiso 1 1 calc . . .
H9B H 0.7707 0.2553 1.1280 0.110 Uiso 1 1 calc . . .
H9C H 0.7532 0.3630 1.0305 0.110 Uiso 1 1 calc . . .
C10 C 0.4599(3) 0.3325(3) 0.9196(3) 0.0526(8) Uani 1 1 d . . .
H10A H 0.5047 0.3864 0.9888 0.063 Uiso 1 1 calc . . .
H10B H 0.4732 0.3658 0.8434 0.063 Uiso 1 1 calc . . .
C11 C 0.3144(3) 0.3354(3) 0.9053(3) 0.0452(7) Uani 1 1 d . . .
C12 C 0.2327(3) 0.4113(3) 0.8157(3) 0.0532(8) Uani 1 1 d . . .
H12 H 0.2688 0.4557 0.7626 0.064 Uiso 1 1 calc . . .
C13 C 0.1011(3) 0.4243(3) 0.8016(3) 0.0605(9) Uani 1 1 d . . .
C14 C 0.0484(3) 0.3568(4) 0.8802(4) 0.0714(10) Uani 1 1 d . . .
H14 H -0.0408 0.3638 0.8725 0.086 Uiso 1 1 calc . . .
C15 C 0.1267(3) 0.2794(4) 0.9695(3) 0.0686(10) Uani 1 1 d . . .
H15 H 0.0897 0.2340 1.0212 0.082 Uiso 1 1 calc . . .
C16 C 0.2589(3) 0.2684(3) 0.9832(3) 0.0542(8) Uani 1 1 d . . .
H16 H 0.3112 0.2164 1.0444 0.065 Uiso 1 1 calc . . .
C17 C 0.0166(4) 0.5107(4) 0.7034(4) 0.0978(15) Uani 1 1 d . . .
H17A H -0.0589 0.4673 0.6517 0.147 Uiso 1 1 calc . . .
H17B H 0.0671 0.5418 0.6515 0.147 Uiso 1 1 calc . . .
H17C H -0.0118 0.5779 0.7448 0.147 Uiso 1 1 calc . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 C1 O2 107.4(2) . . ?
O5 C1 C8 108.4(3) . . ?
O2 C1 C8 109.8(3) . . ?
O5 C1 C7 103.2(2) . . ?
O2 C1 C7 103.6(2) . . ?
C8 C1 C7 123.5(3) . . ?
C1 O2 O3 102.6(2) . . ?
C4 O3 O2 102.8(2) . . ?
O6 C4 O3 107.2(2) . . ?
O6 C4 C9 108.7(3) . . ?
O3 C4 C9 109.5(3) . . ?
O6 C4 C7 103.6(2) . . ?
O3 C4 C7 103.6(2) . . ?
C9 C4 C7 123.2(3) . . ?
C1 O5 O6 103.0(2) . . ?
C4 O6 O5 102.5(2) . . ?
C4 C7 C1 89.9(2) . . ?
C4 C7 C10 114.6(2) . . ?
C1 C7 C10 117.3(2) . . ?
C4 C7 H7 111.1 . . ?
C1 C7 H7 111.1 . . ?
C10 C7 H7 111.1 . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 115.6(2) . . ?
C11 C10 H10A 108.4 . . ?
C7 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C7 C10 H10B 108.4 . . ?
H10A C10 H10B 107.4 . . ?
C12 C11 C16 117.9(3) . . ?
C12 C11 C10 119.5(3) . . ?
C16 C11 C10 122.5(3) . . ?
C13 C12 C11 123.0(3) . . ?
C13 C12 H12 118.5 . . ?
C11 C12 H12 118.5 . . ?
C12 C13 C14 117.9(3) . . ?
C12 C13 C17 120.8(3) . . ?
C14 C13 C17 121.3(3) . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 119.9(3) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O5 1.421(3) . ?
C1 O2 1.430(3) . ?
C1 C8 1.491(4) . ?
C1 C7 1.509(4) . ?
O2 O3 1.502(3) . ?
O3 C4 1.429(3) . ?
C4 O6 1.425(4) . ?
C4 C9 1.489(5) . ?
C4 C7 1.505(4) . ?
O5 O6 1.502(3) . ?
C7 C10 1.524(4) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.507(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.381(4) . ?
C11 C16 1.393(4) . ?
C12 C13 1.368(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(5) . ?
C13 C17 1.514(5) . ?
C14 C15 1.375(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
