#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/97/2229712.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_2229712
loop_
_publ_author_name
'Karpoormath, Rajshekhar'
'Naicker, Tricia'
'Govender, Thavendran'
'Kruger, Hendrik G.'
'Maguire, Glenn E. M.'
_publ_section_title
;
 Benzyl
 5-hydroxy-4-oxapentacyclo[5.4.1.0^2,6^.0^3,10^.0^8,11^]dodecane-3-carboxylate
;
_journal_coeditor_code           IS2678
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o877
_journal_paper_doi               10.1107/S1600536811009020
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H18 O4'
_chemical_formula_moiety         'C19 H18 O4'
_chemical_formula_sum            'C19 H18 O4'
_chemical_formula_weight         310.33
_chemical_name_systematic
;
Benzyl
5-hydroxy-4-oxapentacyclo[5.4.1.0^2,6^.0^3,10^.0^8,11^]dodecane-3-carboxylate
;
_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                 95.2430(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5254(2)
_cell_length_b                   12.8995(2)
_cell_length_c                   16.9772(5)
_cell_measurement_reflns_used    6932
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.41
_cell_volume                     1423.07(6)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1.2° φ and 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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6925
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.238
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3540
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0482
_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)+(0.0463P)²+0.9320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1185
_reflns_number_gt                2930
_reflns_number_total             3540
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is2678.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229712
_cod_database_fobs_code          2229712
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_type_symbol
_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
O O1 0.74558(16) 0.46393(9) 0.05935(6) 0.0284(3) Uani d D 1 . .
H H1 0.695(4) 0.448(2) 0.0053(8) 0.073(8) Uiso d D 1 . .
O O2 0.45389(15) 0.54964(8) 0.09726(6) 0.0223(2) Uani d . 1 . .
O O3 0.06298(17) 0.60878(9) 0.22148(6) 0.0297(3) Uani d . 1 . .
O O4 0.10540(16) 0.65377(8) 0.09589(6) 0.0260(2) Uani d . 1 . .
C C1 0.5554(3) 0.33580(14) 0.29940(9) 0.0311(4) Uani d . 1 . .
H H1A 0.6449 0.3717 0.3411 0.037 Uiso calc R 1 . .
H H1B 0.5203 0.2656 0.3174 0.037 Uiso calc R 1 . .
C C2 0.2721(2) 0.33660(12) 0.19839(9) 0.0279(3) Uani d . 1 . .
H H2 0.1596 0.2865 0.2073 0.034 Uiso calc R 1 . .
C C3 0.2365(2) 0.41085(12) 0.12688(9) 0.0246(3) Uani d . 1 . .
H H3 0.1021 0.4065 0.0937 0.029 Uiso calc R 1 . .
C C4 0.3155(2) 0.52032(11) 0.15444(8) 0.0208(3) Uani d . 1 . .
C C5 0.4540(2) 0.49471(12) 0.23047(9) 0.0244(3) Uani d . 1 . .
H H5 0.4826 0.5553 0.2666 0.029 Uiso calc R 1 . .
C C6 0.3646(2) 0.39964(13) 0.27044(9) 0.0276(3) Uani d . 1 . .
H H6 0.2680 0.4154 0.3113 0.033 Uiso calc R 1 . .
C C7 0.4690(2) 0.29226(12) 0.16299(9) 0.0278(3) Uani d . 1 . .
H H7 0.4703 0.2164 0.1510 0.033 Uiso calc R 1 . .
C C8 0.4308(2) 0.36722(12) 0.09197(9) 0.0250(3) Uani d . 1 . .
H H8 0.4127 0.3363 0.0378 0.030 Uiso calc R 1 . .
C C9 0.5850(2) 0.45678(11) 0.10606(8) 0.0213(3) Uani d . 1 . .
C C10 0.6490(2) 0.45031(12) 0.19510(8) 0.0241(3) Uani d . 1 . .
H H10 0.7798 0.4876 0.2125 0.029 Uiso calc R 1 . .
C C11 0.6469(2) 0.33477(13) 0.21925(9) 0.0284(3) Uani d . 1 . .
H H11 0.7810 0.2975 0.2183 0.034 Uiso calc R 1 . .
C C12 0.1500(2) 0.59911(11) 0.16209(8) 0.0226(3) Uani d . 1 . .
C C13 -0.0640(2) 0.72567(13) 0.09816(9) 0.0286(3) Uani d . 1 . .
H H13A -0.0465 0.7671 0.1474 0.034 Uiso calc R 1 . .
H H13B -0.1952 0.6870 0.0976 0.034 Uiso calc R 1 . .
C C14 -0.0697(2) 0.79630(12) 0.02758(9) 0.0250(3) Uani d . 1 . .
C C15 0.0895(3) 0.80217(13) -0.02124(10) 0.0309(4) Uani d . 1 . .
H H15 0.2077 0.7596 -0.0111 0.037 Uiso calc R 1 . .
C C16 0.0759(3) 0.87050(14) -0.08503(10) 0.0350(4) Uani d . 1 . .
H H16 0.1843 0.8737 -0.1187 0.042 Uiso calc R 1 . .
C C17 -0.0945(3) 0.93378(14) -0.09964(10) 0.0347(4) Uani d . 1 . .
H H17 -0.1025 0.9807 -0.1429 0.042 Uiso calc R 1 . .
C C18 -0.2529(3) 0.92858(13) -0.05118(10) 0.0336(4) Uani d . 1 . .
H H18 -0.3697 0.9722 -0.0610 0.040 Uiso calc R 1 . .
C C19 -0.2416(3) 0.85979(13) 0.01181(10) 0.0296(3) Uani d . 1 . .
H H19 -0.3520 0.8559 0.0445 0.035 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O1 H1 . . 108.6(16) ?
C4 O2 C9 . . 96.46(10) ?
C12 O4 C13 . . 115.11(11) ?
C11 C1 C6 . . 95.19(12) ?
C11 C1 H1A . . 112.7 ?
C6 C1 H1A . . 112.7 ?
C11 C1 H1B . . 112.7 ?
C6 C1 H1B . . 112.7 ?
H1A C1 H1B . . 110.2 ?
C6 C2 C3 . . 108.38(13) ?
C6 C2 C7 . . 102.71(12) ?
C3 C2 C7 . . 89.69(11) ?
C6 C2 H2 . . 117.3 ?
C3 C2 H2 . . 117.3 ?
C7 C2 H2 . . 117.3 ?
C2 C3 C8 . . 90.34(11) ?
C2 C3 C4 . . 107.64(12) ?
C8 C3 C4 . . 100.58(11) ?
C2 C3 H3 . . 118.0 ?
C8 C3 H3 . . 118.0 ?
C4 C3 H3 . . 118.0 ?
O2 C4 C12 . . 112.52(11) ?
O2 C4 C5 . . 105.42(11) ?
C12 C4 C5 . . 116.41(12) ?
O2 C4 C3 . . 104.28(11) ?
C12 C4 C3 . . 114.78(12) ?
C5 C4 C3 . . 102.09(12) ?
C6 C5 C4 . . 108.82(12) ?
C6 C5 C10 . . 103.38(12) ?
C4 C5 C10 . . 101.08(11) ?
C6 C5 H5 . . 114.1 ?
C4 C5 H5 . . 114.1 ?
C10 C5 H5 . . 114.1 ?
C1 C6 C5 . . 103.84(12) ?
C1 C6 C2 . . 102.58(13) ?
C5 C6 C2 . . 101.90(12) ?
C1 C6 H6 . . 115.5 ?
C5 C6 H6 . . 115.5 ?
C2 C6 H6 . . 115.5 ?
C11 C7 C8 . . 108.68(13) ?
C11 C7 C2 . . 103.28(12) ?
C8 C7 C2 . . 89.51(11) ?
C11 C7 H7 . . 117.1 ?
C8 C7 H7 . . 117.1 ?
C2 C7 H7 . . 117.1 ?
C9 C8 C7 . . 106.97(12) ?
C9 C8 C3 . . 102.35(11) ?
C7 C8 C3 . . 90.47(11) ?
C9 C8 H8 . . 117.7 ?
C7 C8 H8 . . 117.7 ?
C3 C8 H8 . . 117.7 ?
O1 C9 O2 . . 110.72(11) ?
O1 C9 C10 . . 114.78(12) ?
O2 C9 C10 . . 104.35(11) ?
O1 C9 C8 . . 118.94(12) ?
O2 C9 C8 . . 103.29(11) ?
C10 C9 C8 . . 103.19(12) ?
C9 C10 C11 . . 107.80(12) ?
C9 C10 C5 . . 101.56(11) ?
C11 C10 C5 . . 102.95(12) ?
C9 C10 H10 . . 114.4 ?
C11 C10 H10 . . 114.4 ?
C5 C10 H10 . . 114.4 ?
C1 C11 C7 . . 102.77(13) ?
C1 C11 C10 . . 103.90(13) ?
C7 C11 C10 . . 101.75(12) ?
C1 C11 H11 . . 115.5 ?
C7 C11 H11 . . 115.5 ?
C10 C11 H11 . . 115.5 ?
O3 C12 O4 . . 124.37(14) ?
O3 C12 C4 . . 122.71(13) ?
O4 C12 C4 . . 112.88(12) ?
O4 C13 C14 . . 109.31(12) ?
O4 C13 H13A . . 109.8 ?
C14 C13 H13A . . 109.8 ?
O4 C13 H13B . . 109.8 ?
C14 C13 H13B . . 109.8 ?
H13A C13 H13B . . 108.3 ?
C15 C14 C19 . . 119.06(15) ?
C15 C14 C13 . . 122.93(14) ?
C19 C14 C13 . . 118.01(14) ?
C14 C15 C16 . . 120.05(16) ?
C14 C15 H15 . . 120.0 ?
C16 C15 H15 . . 120.0 ?
C17 C16 C15 . . 120.37(16) ?
C17 C16 H16 . . 119.8 ?
C15 C16 H16 . . 119.8 ?
C18 C17 C16 . . 119.86(16) ?
C18 C17 H17 . . 120.1 ?
C16 C17 H17 . . 120.1 ?
C17 C18 C19 . . 120.08(16) ?
C17 C18 H18 . . 120.0 ?
C19 C18 H18 . . 120.0 ?
C18 C19 C14 . . 120.57(16) ?
C18 C19 H19 . . 119.7 ?
C14 C19 H19 . . 119.7 ?
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
O1 C9 . 1.3740(17) ?
O1 H1 . 0.969(10) ?
O2 C4 . 1.4355(16) ?
O2 C9 . 1.4715(17) ?
O3 C12 . 1.2081(18) ?
O4 C12 . 1.3362(18) ?
O4 C13 . 1.4463(18) ?
C1 C11 . 1.535(2) ?
C1 C6 . 1.536(2) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C6 . 1.545(2) ?
C2 C3 . 1.547(2) ?
C2 C7 . 1.575(2) ?
C2 H2 . 1.0000 ?
C3 C8 . 1.553(2) ?
C3 C4 . 1.560(2) ?
C3 H3 . 1.0000 ?
C4 C12 . 1.497(2) ?
C4 C5 . 1.542(2) ?
C5 C6 . 1.542(2) ?
C5 C10 . 1.565(2) ?
C5 H5 . 1.0000 ?
C6 H6 . 1.0000 ?
C7 C11 . 1.536(2) ?
C7 C8 . 1.548(2) ?
C7 H7 . 1.0000 ?
C8 C9 . 1.536(2) ?
C8 H8 . 1.0000 ?
C9 C10 . 1.533(2) ?
C10 C11 . 1.546(2) ?
C10 H10 . 1.0000 ?
C11 H11 . 1.0000 ?
C13 C14 . 1.503(2) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.389(2) ?
C14 C19 . 1.395(2) ?
C15 C16 . 1.393(2) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.384(3) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.380(3) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.386(2) ?
C18 H18 . 0.9500 ?
C19 H19 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O2 3_665 0.972(15) 1.910(17) 2.8561(16) 164(2)
C3 H3 O1 1_455 1.00 2.46 3.3716(18) 151
C10 H10 O3 1_655 1.00 2.41 3.3840(19) 163
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C2 C3 C8 . . . . 103.26(13) ?
C7 C2 C3 C8 . . . . -0.05(11) ?
C6 C2 C3 C4 . . . . 2.05(16) ?
C7 C2 C3 C4 . . . . -101.26(12) ?
C9 O2 C4 C12 . . . . -179.39(12) ?
C9 O2 C4 C5 . . . . 52.74(13) ?
C9 O2 C4 C3 . . . . -54.38(12) ?
C2 C3 C4 O2 . . . . 127.36(12) ?
C8 C3 C4 O2 . . . . 33.59(13) ?
C2 C3 C4 C12 . . . . -109.09(14) ?
C8 C3 C4 C12 . . . . 157.15(12) ?
C2 C3 C4 C5 . . . . 17.78(14) ?
C8 C3 C4 C5 . . . . -75.99(13) ?
O2 C4 C5 C6 . . . . -140.89(12) ?
C12 C4 C5 C6 . . . . 93.62(15) ?
C3 C4 C5 C6 . . . . -32.18(14) ?
O2 C4 C5 C10 . . . . -32.49(14) ?
C12 C4 C5 C10 . . . . -157.98(12) ?
C3 C4 C5 C10 . . . . 76.22(13) ?
C11 C1 C6 C5 . . . . -51.77(14) ?
C11 C1 C6 C2 . . . . 54.05(14) ?
C4 C5 C6 C1 . . . . 139.75(13) ?
C10 C5 C6 C1 . . . . 32.92(14) ?
C4 C5 C6 C2 . . . . 33.42(15) ?
C10 C5 C6 C2 . . . . -73.42(13) ?
C3 C2 C6 C1 . . . . -128.27(13) ?
C7 C2 C6 C1 . . . . -34.31(14) ?
C3 C2 C6 C5 . . . . -20.96(15) ?
C7 C2 C6 C5 . . . . 73.00(14) ?
C6 C2 C7 C11 . . . . 0.35(15) ?
C3 C2 C7 C11 . . . . 109.13(12) ?
C6 C2 C7 C8 . . . . -108.74(12) ?
C3 C2 C7 C8 . . . . 0.05(11) ?
C11 C7 C8 C9 . . . . -0.84(16) ?
C2 C7 C8 C9 . . . . 103.02(12) ?
C11 C7 C8 C3 . . . . -103.91(13) ?
C2 C7 C8 C3 . . . . -0.05(11) ?
C2 C3 C8 C9 . . . . -107.44(12) ?
C4 C3 C8 C9 . . . . 0.58(14) ?
C2 C3 C8 C7 . . . . 0.05(12) ?
C4 C3 C8 C7 . . . . 108.07(12) ?
C4 O2 C9 O1 . . . . -177.16(11) ?
C4 O2 C9 C10 . . . . -53.15(12) ?
C4 O2 C9 C8 . . . . 54.46(12) ?
C7 C8 C9 O1 . . . . 109.05(14) ?
C3 C8 C9 O1 . . . . -156.62(12) ?
C7 C8 C9 O2 . . . . -127.86(12) ?
C3 C8 C9 O2 . . . . -33.53(13) ?
C7 C8 C9 C10 . . . . -19.38(14) ?
C3 C8 C9 C10 . . . . 74.95(13) ?
O1 C9 C10 C11 . . . . -97.66(15) ?
O2 C9 C10 C11 . . . . 140.99(12) ?
C8 C9 C10 C11 . . . . 33.31(14) ?
O1 C9 C10 C5 . . . . 154.53(13) ?
O2 C9 C10 C5 . . . . 33.17(14) ?
C8 C9 C10 C5 . . . . -74.51(13) ?
C6 C5 C10 C9 . . . . 111.60(13) ?
C4 C5 C10 C9 . . . . -1.00(14) ?
C6 C5 C10 C11 . . . . 0.06(14) ?
C4 C5 C10 C11 . . . . -112.55(12) ?
C6 C1 C11 C7 . . . . -53.88(14) ?
C6 C1 C11 C10 . . . . 51.86(14) ?
C8 C7 C11 C1 . . . . 127.80(13) ?
C2 C7 C11 C1 . . . . 33.76(15) ?
C8 C7 C11 C10 . . . . 20.41(15) ?
C2 C7 C11 C10 . . . . -73.63(14) ?
C9 C10 C11 C1 . . . . -139.89(12) ?
C5 C10 C11 C1 . . . . -33.04(14) ?
C9 C10 C11 C7 . . . . -33.39(15) ?
C5 C10 C11 C7 . . . . 73.46(13) ?
C13 O4 C12 O3 . . . . -2.0(2) ?
C13 O4 C12 C4 . . . . 175.61(12) ?
O2 C4 C12 O3 . . . . -154.75(14) ?
C5 C4 C12 O3 . . . . -32.9(2) ?
C3 C4 C12 O3 . . . . 86.21(18) ?
O2 C4 C12 O4 . . . . 27.56(17) ?
C5 C4 C12 O4 . . . . 149.38(13) ?
C3 C4 C12 O4 . . . . -91.48(15) ?
C12 O4 C13 C14 . . . . 168.61(13) ?
O4 C13 C14 C15 . . . . -11.6(2) ?
O4 C13 C14 C19 . . . . 169.54(13) ?
C19 C14 C15 C16 . . . . -0.2(2) ?
C13 C14 C15 C16 . . . . -178.99(16) ?
C14 C15 C16 C17 . . . . 0.8(3) ?
C15 C16 C17 C18 . . . . -0.6(3) ?
C16 C17 C18 C19 . . . . -0.3(3) ?
C17 C18 C19 C14 . . . . 0.9(3) ?
C15 C14 C19 C18 . . . . -0.6(2) ?
C13 C14 C19 C18 . . . . 178.21(15) ?
