#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/14/2011433.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2011433
loop_
_publ_author_name
'Ellis, Dianne D.'
'Spek, Anthony L.'
_publ_section_title
;
 (5S)-3-Oxo-4-oxa-endo-tricyclo[5.2.1.0^2,6^]dec-8-en-5-yl
 acetate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1269
_journal_page_last               1270
_journal_paper_doi               10.1107/S0108270100010179
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C11 H12 O4'
_chemical_formula_sum            'C11 H12 O4'
_chemical_formula_weight         208.21
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4538(8)
_cell_length_b                   7.5568(7)
_cell_length_c                   17.6385(13)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      13.97
_cell_measurement_theta_min      9.73
_cell_volume                     993.52(16)
_computing_cell_refinement       'SET4 (de Boer & Duisenberg, 1984)'
_computing_data_collection
'locally modified CAD4-Version 5 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2000)'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD4T'
_diffrn_measurement_method       w/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0229
_diffrn_reflns_av_sigmaI/netI    .0226
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3710
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        2.2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .106
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             440
_exptl_crystal_size_max          .50
_exptl_crystal_size_mid          .50
_exptl_crystal_size_min          .50
_refine_diff_density_max         .171
_refine_diff_density_min         -.242
_refine_ls_abs_structure_details 'see experimental'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          .0395
_refine_ls_R_factor_gt           .0341
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0449P)²+0.1472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0825
_reflns_number_gt                1213
_reflns_number_total             1334
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            os1119.cif
_cod_data_source_block           I
_cod_database_code               2011433
_cod_database_fobs_code          2011433
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 -.0254(2) .3942(3) .19351(10) .0204(4) Uani d . 1 . . C
H1 -.0448 .4530 .2437 .028(6) Uiso calc R 1 . . H
C2 .1636(2) .3264(2) .18536(10) .0218(4) Uani d . 1 . . C
O3 .24164(16) .39637(18) .12243(7) .0238(3) Uani d . 1 . . O
C4 .1383(2) .5390(2) .09274(10) .0215(4) Uani d . 1 . . C
H4 .1340 .5360 .0361 .021(5) Uiso calc R 1 . . H
C5 -.0487(2) .5251(3) .12713(10) .0223(4) Uani d . 1 . . C
H5 -.0901 .6431 .1460 .025(6) Uiso calc R 1 . . H
C6 -.1972(3) .4352(3) .07829(11) .0296(5) Uani d . 1 . . C
H6 -.2570 .5127 .0399 .032(6) Uiso calc R 1 . . H
C7 -.1257(3) .2615(3) .04904(11) .0327(5) Uani d . 1 . . C
H7 -.0962 .2358 -.0022 .043(6) Uiso calc R 1 . . H
C8 -.1111(3) .1514(3) .10681(12) .0298(5) Uani d . 1 . . C
H8 -.0701 .0325 .1046 .051(8) Uiso calc R 1 . . H
C9 -.1715(2) .2492(3) .17728(10) .0239(4) Uani d . 1 . . C
H9 -.2078 .1741 .2214 .029(6) Uiso calc R 1 . . H
C10 -.3181(2) .3680(3) .14336(11) .0286(5) Uani d . 1 . . C
H10A -.3565 .4635 .1782 .028(5) Uiso calc R 1 . . H
H10B -.4234 .3005 .1251 .031(6) Uiso calc R 1 . . H
O11 .24175(19) .2223(2) .22411(9) .0344(4) Uani d . 1 . . O
O12 .21915(17) .69783(17) .11977(8) .0246(3) Uani d . 1 . . O
C13 .3743(3) .7491(3) .08444(10) .0256(4) Uani d . 1 . . C
C14 .4628(3) .8931(3) .12751(14) .0427(6) Uani d . 1 . . C
H14A .5640 .9393 .0981 .072(10) Uiso calc R 1 . . H
H14B .5066 .8467 .1760 .095(12) Uiso calc R 1 . . H
H14C .3765 .9883 .1369 .084(11) Uiso calc R 1 . . H
O15 .42704(19) .68259(19) .02715(8) .0327(4) Uani d . 1 . . O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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_publ_flag
C2 C1 C5 104.56(14) ?
C2 C1 C9 113.17(15) ?
C5 C1 C9 103.35(14) ?
C2 C1 H1 111.7 ?
C5 C1 H1 111.7 ?
C9 C1 H1 111.7 ?
O11 C2 O3 120.96(17) ?
O11 C2 C1 128.77(17) ?
O3 C2 C1 110.23(15) ?
C2 O3 C4 111.26(14) ?
O3 C4 O12 106.58(13) ?
O3 C4 C5 107.23(14) ?
O12 C4 C5 108.17(15) ?
O3 C4 H4 111.5 ?
O12 C4 H4 111.5 ?
C5 C4 H4 111.5 ?
C4 C5 C1 104.07(14) ?
C4 C5 C6 117.36(15) ?
C1 C5 C6 102.70(15) ?
C4 C5 H5 110.7 ?
C1 C5 H5 110.7 ?
C6 C5 H5 110.7 ?
C7 C6 C10 100.04(17) ?
C7 C6 C5 108.53(16) ?
C10 C6 C5 98.44(15) y
C7 C6 H6 115.8 ?
C10 C6 H6 115.8 ?
C5 C6 H6 115.8 ?
C8 C7 C6 108.30(16) ?
C8 C7 H7 125.9 ?
C6 C7 H7 125.9 ?
C7 C8 C9 107.53(17) ?
C7 C8 H8 126.2 ?
C9 C8 H8 126.2 ?
C8 C9 C10 100.20(15) ?
C8 C9 C1 106.48(14) ?
C10 C9 C1 98.99(15) y
C8 C9 H9 116.2 ?
C10 C9 H9 116.2 ?
C1 C9 H9 116.2 ?
C9 C10 C6 93.82(14) y
C9 C10 H10A 113.0 ?
C6 C10 H10A 113.0 ?
C9 C10 H10B 113.0 ?
C6 C10 H10B 113.0 ?
H10A C10 H10B 110.4 ?
C13 O12 C4 116.33(15) ?
O15 C13 O12 122.91(18) ?
O15 C13 C14 126.55(19) ?
O12 C13 C14 110.53(16) ?
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 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.506(3) ?
C1 C5 . 1.543(2) ?
C1 C9 . 1.572(3) ?
C1 H1 . 1.0000 ?
C2 O11 . 1.194(2) y
C2 O3 . 1.360(2) y
O3 C4 . 1.425(2) y
C4 O12 . 1.425(2) y
C4 C5 . 1.524(3) ?
C4 H4 . 1.0000 ?
C5 C6 . 1.559(3) ?
C5 H5 . 1.0000 ?
C6 C7 . 1.507(3) ?
C6 C10 . 1.545(3) ?
C6 H6 . 1.0000 ?
C7 C8 . 1.320(3) ?
C7 H7 . .9500 ?
C8 C9 . 1.515(3) ?
C8 H8 . .9500 ?
C9 C10 . 1.536(3) ?
C9 H9 . 1.0000 ?
C10 H10A . .9900 ?
C10 H10B . .9900 ?
O12 C13 . 1.369(2) y
C13 O15 . 1.195(2) y
C13 C14 . 1.482(3) ?
C14 H14A . .9800 ?
C14 H14B . .9800 ?
C14 H14C . .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_publ_flag
C5 C1 C2 O11 179.82(19) ?
C9 C1 C2 O11 -68.4(2) ?
C5 C1 C2 O3 -2.61(19) ?
C9 C1 C2 O3 109.14(16) ?
O11 C2 O3 C4 -169.71(17) y
C1 C2 O3 C4 12.50(19) ?
C2 O3 C4 O12 98.48(16) ?
C2 O3 C4 C5 -17.17(19) ?
O3 C4 C5 C1 14.44(18) ?
O12 C4 C5 C1 -100.16(16) ?
O3 C4 C5 C6 -98.20(18) ?
O12 C4 C5 C6 147.20(16) ?
C2 C1 C5 C4 -7.24(18) ?
C9 C1 C5 C4 -125.89(15) ?
C2 C1 C5 C6 115.59(16) ?
C9 C1 C5 C6 -3.06(17) ?
C4 C5 C6 C7 49.6(2) ?
C1 C5 C6 C7 -63.81(18) ?
C4 C5 C6 C10 153.23(17) ?
C1 C5 C6 C10 39.82(18) ?
C10 C6 C7 C8 -32.7(2) ?
C5 C6 C7 C8 69.9(2) ?
C6 C7 C8 C9 -.4(2) ?
C7 C8 C9 C10 33.6(2) ?
C7 C8 C9 C1 -69.0(2) ?
C2 C1 C9 C8 -44.0(2) ?
C5 C1 C9 C8 68.50(18) ?
C2 C1 C9 C10 -147.52(16) ?
C5 C1 C9 C10 -35.02(17) ?
C8 C9 C10 C6 -49.74(17) ?
C1 C9 C10 C6 58.94(16) ?
C7 C6 C10 C9 49.44(17) ?
C5 C6 C10 C9 -61.21(17) ?
O3 C4 O12 C13 76.42(17) ?
C5 C4 O12 C13 -168.55(15) ?
C4 O12 C13 O15 10.9(3) y
C4 O12 C13 C14 -168.50(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21182340
2 PubChem 139057955
