#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:55:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178450 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/71/4027154.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_4027154
loop_
_publ_author_name
'Nicole M. Cain'
'Edward R. T. Tiekink'
'Dennis K. Taylor'
_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
_chemical_name_systematic
;
 ?
;
_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  AFC12Κ/SATURN724
_diffrn_measurement_method       ω
_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/[σ²(Fo²)+(0.053P)²+0.7483P] where P=(Fo²+2Fc²)/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>2σ(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
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
O1 O 0.17566(9) -0.06482(14) 0.60983(7) 0.0159(2) Uani 1 1 d .
O2 O 0.15274(9) 0.13438(14) 0.63125(7) 0.0165(2) Uani 1 1 d .
O9 O 0.11309(10) 0.42420(15) 0.71102(7) 0.0212(3) Uani 1 1 d .
O12 O 0.24705(12) 0.13783(18) 0.43049(7) 0.0303(3) Uani 1 1 d .
O15 O 0.32176(10) 0.52727(16) 0.74259(7) 0.0236(3) Uani 1 1 d .
C3 C 0.27324(13) 0.2039(2) 0.69376(9) 0.0153(3) Uani 1 1 d .
C4 C 0.37894(13) 0.2146(2) 0.64763(9) 0.0177(3) Uani 1 1 d .
H4A H 0.3548 0.3138 0.6016 0.021 Uiso 1 1 calc R
H4B H 0.4639 0.2511 0.6904 0.021 Uiso 1 1 calc R
C5 C 0.39366(13) 0.0227(2) 0.60644(10) 0.0173(3) Uani 1 1 d .
H5A H 0.4478 0.0397 0.5667 0.021 Uiso 1 1 calc R
H5B H 0.4401 -0.0675 0.6531 0.021 Uiso 1 1 calc R
C6 C 0.26075(13) -0.0613(2) 0.55517(9) 0.0147(3) Uani 1 1 d .
C7 C 0.31251(15) 0.0826(2) 0.77675(9) 0.0202(3) Uani 1 1 d .
H7A H 0.2407 0.0819 0.8029 0.030 Uiso 1 1 calc R
H7B H 0.3917 0.1362 0.8186 0.030 Uiso 1 1 calc R
H7C H 0.3303 -0.0482 0.7621 0.030 Uiso 1 1 calc R
C8 C 0.23983(13) 0.4050(2) 0.71815(9) 0.0160(3) Uani 1 1 d .
C10 C 0.07331(16) 0.6085(2) 0.73568(12) 0.0252(3) Uani 1 1 d .
H10A H 0.1387 0.6531 0.7894 0.038 Uiso 1 1 calc R
H10B H -0.0123 0.5964 0.7458 0.038 Uiso 1 1 calc R
H10C H 0.0666 0.7005 0.6885 0.038 Uiso 1 1 calc R
C11 C 0.19080(15) 0.0527(2) 0.47356(9) 0.0195(3) Uani 1 1 d .
H11 H 0.0975 0.0570 0.4556 0.023 Uiso 1 1 calc R
C13 C 0.27152(13) -0.2748(2) 0.53268(9) 0.0169(3) Uani 1 1 d .
H13 H 0.3085 -0.3439 0.5894 0.020 Uiso 1 1 calc R
C14 C 0.36724(15) -0.3049(2) 0.47991(10) 0.0221(3) Uani 1 1 d .
H14A H 0.4519 -0.2460 0.5107 0.033 Uiso 1 1 calc R
H14B H 0.3315 -0.2460 0.4221 0.033 Uiso 1 1 calc R
H14C H 0.3796 -0.4418 0.4731 0.033 Uiso 1 1 calc R
C15 C 0.13790(15) -0.3651(2) 0.48629(11) 0.0239(3) Uani 1 1 d .
H15A H 0.0782 -0.3441 0.5212 0.036 Uiso 1 1 calc R
H15B H 0.1490 -0.5023 0.4795 0.036 Uiso 1 1 calc R
H15C H 0.1009 -0.3066 0.4285 0.036 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 '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
C6 O1 O2 107.78(9)
C3 O2 O1 107.63(9)
C8 O9 C10 116.21(12)
O2 C3 C7 111.38(11)
O2 C3 C4 108.18(11)
C7 C3 C4 113.74(12)
O2 C3 C8 104.95(10)
C7 C3 C8 108.23(11)
C4 C3 C8 110.00(11)
C5 C4 C3 110.77(11)
C5 C4 H4A 109.5
C3 C4 H4A 109.5
C5 C4 H4B 109.5
C3 C4 H4B 109.5
H4A C4 H4B 108.1
C6 C5 C4 111.80(11)
C6 C5 H5A 109.3
C4 C5 H5A 109.3
C6 C5 H5B 109.3
C4 C5 H5B 109.3
H5A C5 H5B 107.9
O1 C6 C11 107.28(11)
O1 C6 C5 109.53(11)
C11 C6 C5 113.14(12)
O1 C6 C13 103.29(10)
C11 C6 C13 111.00(11)
C5 C6 C13 112.01(11)
C3 C7 H7A 109.5
C3 C7 H7B 109.5
H7A C7 H7B 109.5
C3 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O15 C8 O9 125.18(14)
O15 C8 C3 122.39(13)
O9 C8 C3 112.42(12)
O9 C10 H10A 109.5
O9 C10 H10B 109.5
H10A C10 H10B 109.5
O9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O12 C11 C6 123.68(14)
O12 C11 H11 118.2
C6 C11 H11 118.2
C14 C13 C15 110.86(12)
C14 C13 C6 111.81(12)
C15 C13 C6 112.80(12)
C14 C13 H13 107.0
C15 C13 H13 107.0
C6 C13 H13 107.0
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C13 C15 H15A 109.5
C13 C15 H15B 109.5
H15A C15 H15B 109.5
C13 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.4435(16)
O1 O2 1.4767(14)
O2 C3 1.4536(16)
O9 C8 1.3307(17)
O9 C10 1.4528(18)
O12 C11 1.2037(19)
O15 C8 1.2026(18)
C3 C7 1.527(2)
C3 C4 1.5298(19)
C3 C8 1.534(2)
C4 C5 1.528(2)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.5256(19)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C11 1.521(2)
C6 C13 1.552(2)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11 0.9500
C13 C14 1.5286(19)
C13 C15 1.531(2)
C13 H13 1.0000
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 O1 O2 C3 -72.79(12)
O1 O2 C3 C7 -59.14(13)
O1 O2 C3 C4 66.57(13)
O1 O2 C3 C8 -176.02(9)
O2 C3 C4 C5 -54.35(15)
C7 C3 C4 C5 69.96(15)
C8 C3 C4 C5 -168.46(11)
C3 C4 C5 C6 46.91(16)
O2 O1 C6 C11 -59.60(12)
O2 O1 C6 C5 63.57(13)
O2 O1 C6 C13 -176.93(9)
C4 C5 C6 O1 -51.98(15)
C4 C5 C6 C11 67.64(15)
C4 C5 C6 C13 -165.98(11)
C10 O9 C8 O15 -0.4(2)
C10 O9 C8 C3 178.01(12)
O2 C3 C8 O15 -153.36(13)
C7 C3 C8 O15 87.61(16)
C4 C3 C8 O15 -37.21(18)
O2 C3 C8 O9 28.14(14)
C7 C3 C8 O9 -90.88(14)
C4 C3 C8 O9 144.30(12)
O1 C6 C11 O12 153.37(14)
C5 C6 C11 O12 32.5(2)
C13 C6 C11 O12 -94.46(17)
O1 C6 C13 C14 -175.67(11)
C11 C6 C13 C14 69.64(15)
C5 C6 C13 C14 -57.89(15)
O1 C6 C13 C15 58.58(14)
C11 C6 C13 C15 -56.10(16)
C5 C6 C13 C15 176.36(12)
