#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:39:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178436 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/57/4025765.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_4025765
loop_
_publ_author_name
'Tyrone C. Casey'
'Julie Carlisle'
'Patrizia Tisselli'
'Louise Male'
'Neil Spencer'
'Richard S. Grainger'
_publ_contact_author_address
;
School of Chemistry, University of Birmingham, Edgbaston,
Birmingham, B15 2TT, UK.
;
_publ_contact_author_email       r.s.grainger@bham.ac.uk
_publ_contact_author_fax         '0121 414 4403'
_publ_contact_author_name        'Richard S. Grainger'
_publ_contact_author_phone       '0121 414 4465'
_publ_section_title
;
 Stereoselective α,α'-Annelation Reactions of 1,3-Dioxan-5-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7461
_journal_page_last               7464
_journal_paper_doi               10.1021/jo101531b
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C11 H16 O5'
_chemical_formula_sum            'C11 H16 O5'
_chemical_formula_weight         228.24
_chemical_name_systematic
;
Methyl 3,3-Dimethyl-9-oxo-2,4-dioxabicyclo[3.3.1]nonane-7α-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.7380(10)
_cell_angle_beta                 107.450(2)
_cell_angle_gamma                94.121(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9524(2)
_cell_length_b                   8.2007(2)
_cell_length_c                   9.4468(2)
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     546.84(2)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution
;
SIR92, (Altomare, Cascarano, Giacovazzo, Guagliardi, Burla, Polidori &
Camalli, 1994)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13210
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.74
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_correction_T_min  0.9891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0385
_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)+(0.0311P)²+0.2891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0933
_reflns_number_gt                2185
_reflns_number_total             2497
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo101531b_si_001.cif
_cod_data_source_block           5a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025765
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.42350(16) 0.31305(16) 0.60677(15) 0.0175(3) Uani 1 1 d . . .
C2 C 0.48157(16) 0.37688(16) 0.78602(14) 0.0165(2) Uani 1 1 d . . .
H2 H 0.5837 0.4789 0.8372 0.020 Uiso 1 1 calc R . .
C3 C 0.53678(16) 0.21584(16) 0.82435(15) 0.0179(3) Uani 1 1 d . . .
H3A H 0.5841 0.2465 0.9411 0.022 Uiso 1 1 calc R . .
H3B H 0.6329 0.1783 0.7817 0.022 Uiso 1 1 calc R . .
C4 C 0.37332(16) 0.06480(16) 0.74982(15) 0.0177(3) Uani 1 1 d . . .
H4 H 0.4235 -0.0433 0.7511 0.021 Uiso 1 1 calc R . .
C5 C 0.27054(17) 0.03104(16) 0.57344(15) 0.0190(3) Uani 1 1 d . . .
H5A H 0.1520 -0.0431 0.5420 0.023 Uiso 1 1 calc R . .
H5B H 0.3372 -0.0363 0.5086 0.023 Uiso 1 1 calc R . .
C6 C 0.24090(16) 0.19724(16) 0.53266(14) 0.0180(3) Uani 1 1 d . . .
H6 H 0.2000 0.1651 0.4146 0.022 Uiso 1 1 calc R . .
C7 C 0.18049(16) 0.43815(16) 0.72809(14) 0.0177(3) Uani 1 1 d . . .
C8 C 0.25051(17) 0.08158(16) 0.84790(15) 0.0185(3) Uani 1 1 d . . .
C9 C 0.23976(19) 0.1552(2) 1.10758(16) 0.0266(3) Uani 1 1 d . . .
H9A H 0.3184 0.2094 1.2189 0.040 Uiso 1 1 calc R . .
H9B H 0.1797 0.0377 1.0888 0.040 Uiso 1 1 calc R . .
H9C H 0.1496 0.2272 1.0845 0.040 Uiso 1 1 calc R . .
C10 C 0.22510(18) 0.59385(17) 0.68220(16) 0.0223(3) Uani 1 1 d . . .
H10A H 0.3081 0.5681 0.6228 0.033 Uiso 1 1 calc R . .
H10B H 0.2812 0.6981 0.7786 0.033 Uiso 1 1 calc R . .
H10C H 0.1147 0.6154 0.6156 0.033 Uiso 1 1 calc R . .
C11 C 0.03795(18) 0.46139(18) 0.80497(17) 0.0242(3) Uani 1 1 d . . .
H11A H -0.0739 0.4681 0.7289 0.036 Uiso 1 1 calc R . .
H11B H 0.0777 0.5697 0.8988 0.036 Uiso 1 1 calc R . .
H11C H 0.0176 0.3614 0.8371 0.036 Uiso 1 1 calc R . .
O1 O 0.52390(12) 0.32701(13) 0.53478(11) 0.0235(2) Uani 1 1 d . . .
O2 O 0.33375(11) 0.41555(11) 0.84120(10) 0.0174(2) Uani 1 1 d . . .
O3 O 0.11060(11) 0.27989(11) 0.59267(10) 0.0193(2) Uani 1 1 d . . .
O4 O 0.08968(12) 0.03571(13) 0.79538(11) 0.0257(2) Uani 1 1 d . . .
O5 O 0.34520(12) 0.14222(13) 1.00513(11) 0.0221(2) Uani 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 124.51(11) . . ?
O1 C1 C2 123.62(11) . . ?
C6 C1 C2 110.56(10) . . ?
O2 C2 C1 111.72(9) . . ?
O2 C2 C3 106.40(9) . . ?
C1 C2 C3 103.36(10) . . ?
O2 C2 H2 111.7 . . ?
C1 C2 H2 111.7 . . ?
C3 C2 H2 111.7 . . ?
C2 C3 C4 109.85(10) . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C8 C4 C5 112.58(10) . . ?
C8 C4 C3 113.29(10) . . ?
C5 C4 C3 113.09(10) . . ?
C8 C4 H4 105.7 . . ?
C5 C4 H4 105.7 . . ?
C3 C4 H4 105.7 . . ?
C4 C5 C6 115.23(10) . . ?
C4 C5 H5A 108.5 . . ?
C6 C5 H5A 108.5 . . ?
C4 C5 H5B 108.5 . . ?
C6 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
O3 C6 C1 112.27(10) . . ?
O3 C6 C5 111.65(10) . . ?
C1 C6 C5 104.55(10) . . ?
O3 C6 H6 109.4 . . ?
C1 C6 H6 109.4 . . ?
C5 C6 H6 109.4 . . ?
O3 C7 O2 109.58(10) . . ?
O3 C7 C11 105.53(10) . . ?
O2 C7 C11 106.05(10) . . ?
O3 C7 C10 111.80(10) . . ?
O2 C7 C10 111.37(10) . . ?
C11 C7 C10 112.18(11) . . ?
O4 C8 O5 122.76(12) . . ?
O4 C8 C4 125.63(12) . . ?
O5 C8 C4 111.41(10) . . ?
O5 C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 O2 C2 115.03(9) . . ?
C7 O3 C6 115.67(9) . . ?
C8 O5 C9 115.31(10) . . ?
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 O1 1.2147(15) . ?
C1 C6 1.5052(17) . ?
C1 C2 1.5105(17) . ?
C2 O2 1.4385(14) . ?
C2 C3 1.5373(17) . ?
C2 H2 1.0000 . ?
C3 C4 1.5424(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C8 1.5203(17) . ?
C4 C5 1.5412(17) . ?
C4 H4 1.0000 . ?
C5 C6 1.5462(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O3 1.4355(14) . ?
C6 H6 1.0000 . ?
C7 O3 1.4258(15) . ?
C7 O2 1.4284(15) . ?
C7 C11 1.5115(17) . ?
C7 C10 1.5254(17) . ?
C8 O4 1.2058(16) . ?
C8 O5 1.3496(15) . ?
C9 O5 1.4438(15) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 154.67(11) . . . . ?
C6 C1 C2 O2 -37.92(13) . . . . ?
O1 C1 C2 C3 -91.32(14) . . . . ?
C6 C1 C2 C3 76.10(12) . . . . ?
O2 C2 C3 C4 55.29(12) . . . . ?
C1 C2 C3 C4 -62.51(12) . . . . ?
C2 C3 C4 C8 -80.75(12) . . . . ?
C2 C3 C4 C5 48.90(13) . . . . ?
C8 C4 C5 C6 86.86(13) . . . . ?
C3 C4 C5 C6 -43.15(14) . . . . ?
O1 C1 C6 O3 -139.49(12) . . . . ?
C2 C1 C6 O3 53.22(13) . . . . ?
O1 C1 C6 C5 99.30(14) . . . . ?
C2 C1 C6 C5 -67.98(12) . . . . ?
C4 C5 C6 O3 -71.85(13) . . . . ?
C4 C5 C6 C1 49.76(13) . . . . ?
C5 C4 C8 O4 16.34(17) . . . . ?
C3 C4 C8 O4 146.25(13) . . . . ?
C5 C4 C8 O5 -168.76(10) . . . . ?
C3 C4 C8 O5 -38.86(14) . . . . ?
O3 C7 O2 C2 61.73(12) . . . . ?
C11 C7 O2 C2 175.19(9) . . . . ?
C10 C7 O2 C2 -62.51(13) . . . . ?
C1 C2 O2 C7 -17.92(13) . . . . ?
C3 C2 O2 C7 -130.04(10) . . . . ?
O2 C7 O3 C6 -45.17(13) . . . . ?
C11 C7 O3 C6 -158.96(10) . . . . ?
C10 C7 O3 C6 78.81(13) . . . . ?
C1 C6 O3 C7 -10.82(14) . . . . ?
C5 C6 O3 C7 106.21(11) . . . . ?
O4 C8 O5 C9 -2.34(18) . . . . ?
C4 C8 O5 C9 -177.40(10) . . . . ?
