#------------------------------------------------------------------------------
#$Date: 2018-06-13 23:43:27 +0300 (Wed, 13 Jun 2018) $
#$Revision: 208347 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/73/2007392.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_2007392
loop_
_publ_author_name
'Thalji, Reema K.'
'Pentes, Howard G.'
'Fischer, Nikolaus H.'
'Fronczek, Frank R.'
_publ_section_title
;
 8-Desacetoxy-11βH,13-dihydroperoxyferolide, a Sesquiterpene
 Lactone Hydroperoxide
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              861
_journal_page_last               863
_journal_paper_doi               10.1107/S0108270197020088
_journal_volume                  54
_journal_year                    1998
_chemical_formula_iupac          'C15 H22 O5'
_chemical_formula_sum            'C15 H22 O5'
_chemical_formula_weight         282.34
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                70.190(8)
_cell_angle_beta                 85.259(6)
_cell_angle_gamma                78.188(6)
_cell_formula_units_Z            1
_cell_length_a                   5.7473(3)
_cell_length_b                   7.6109(7)
_cell_length_c                   9.0705(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      38
_cell_measurement_theta_min      23
_cell_volume                     365.34(6)
_computing_cell_refinement       'CAD-4 Operations Manual'
_computing_data_collection
'CAD-4 Operations Manual (Enraf-Nonius, 1977)'
_computing_data_reduction        'PROCESS in MolEN (Fair, 1990)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'BTABLE PTABLE CIF IN in MolEN'
_computing_structure_refinement  'LSFM in MolEN'
_computing_structure_solution
'MULTAN80 (Main et al., 1980) (direct methods)'
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2951
_diffrn_reflns_theta_max         75
_diffrn_standards_decay_%        2.5
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.75
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   '\y scans (North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             152
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.24
_refine_ls_abs_structure_details
;
assumed to correspond to the accepted absolute configuration of sesquiterpene
lactones from higher plants (Fischer et al., 1979)
;
_refine_ls_extinction_coef       1.5E-5(2)
_refine_ls_extinction_method     'isotropic (Zachariasen, 1963)'
_refine_ls_goodness_of_fit_obs   1.94
_refine_ls_hydrogen_treatment
'H atoms treated by a mixture of independent and constrained refinement'
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2924
_refine_ls_R_factor_obs          .040
_refine_ls_shift/esd_max         0.02
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 4Fo²/[σ²(Fo²) + 0.0004Fo⁴]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         .054
_reflns_number_observed          2924
_reflns_number_total             2951
_reflns_observed_criterion       I>0
_cod_data_source_file            sx1065.cif
_cod_data_source_block           seslacOOH
_cod_depositor_comments
;
 Updating space group information.

 Antanas Vaitkus,
 2018-06-14

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 4Fo^2^/[\s^2^(Fo^2^) +
0.0004Fo^4^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0004Fo^4^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_formula_sum        C15H22O5
_cod_database_code               2007392
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
O1 0 0 0 .0566(5) Uani ? 1.0
O2 -.1267(2) .3605(2) -.27170(10) .0585(5) Uani ? 1.0
O3 -.3215(3) .5993(2) -.4636(2) .0695(7) Uani ? 1.0
O4A .4452(3) .2551(2) .4264(2) .0756(8) Uani ? .92
O5A .3499(3) .4068(3) .4921(2) .1010(9) Uani ? .92
C1 .2431(4) .2321(3) .3521(2) .0637(9) Uani ? 1.0
C2 .3346(4) .0375(3) .3365(3) .0710(10) Uani ? 1.0
C3 .1719(4) -.0389(3) .2560(3) .0654(9) Uani ? 1.0
C4 .1931(3) .0271(2) .0790(2) .0525(7) Uani ? 1.0
C5 .0141(3) .1893(2) -.0092(2) .0451(6) Uani ? 1.0
C6 .0625(3) .3318(2) -.1620(2) .0477(6) Uani ? 1.0
C7 .0468(3) .5297(2) -.1506(2) .0453(6) Uani ? 1.0
C8 .2617(3) .5688(2) -.0881(2) .0539(7) Uani ? 1.0
C9 .3521(3) .4320(2) .0722(2) .0501(7) Uani ? 1.0
C10 .1761(3) .4034(2) .2064(2) .0483(6) Uani ? 1.0
C11 -.0244(3) .6578(2) -.3169(2) .0520(7) Uani ? 1.0
C12 -.1738(3) .5425(2) -.3619(2) .0551(7) Uani ? 1.0
C13 -.1512(4) .8578(3) -.3348(2) .0660(10) Uani ? 1.0
C14 -.0208(4) .5266(3) .2085(2) .0597(8) Uani ? 1.0
C15 .4319(3) -.0285(3) .0099(3) .0750(10) Uani ? 1.0
O4B .275(3) .281(2) .488(2) .055(3) Uiso ? .08
O5B .531(3) .308(3) .436(2) .073(5) Uiso ? .08
H5O .512(5) .436(5) .495(4) .1267 Uiso ? .92
H5 -.102(3) .248(2) .049(2) .039(4) Uiso ? 1.0
H1 .0938 .2319 .4055 .0840 Uiso calc 1.0
H2a .3645 -.0508 .4391 .0966 Uiso calc 1.0
H2b .4796 .0430 .2781 .0966 Uiso calc 1.0
H3a .0119 .0015 .2838 .0903 Uiso calc 1.0
H3b .2105 -.1739 .2937 .0903 Uiso calc 1.0
H6 .2171 .2838 -.1938 .0591 Uiso calc 1.0
H7 -.0635 .5507 -.0715 .0574 Uiso calc 1.0
H8a .2209 .6930 -.0808 .0665 Uiso calc 1.0
H8b .3883 .5646 -.1619 .0665 Uiso calc 1.0
H9a .4775 .4787 .0997 .0639 Uiso calc 1.0
H9b .4125 .3113 .0609 .0639 Uiso calc 1.0
H11 .1099 .6848 -.3830 .0671 Uiso calc 1.0
H13a -.1871 .9249 -.4420 .0891 Uiso calc 1.0
H13b -.2943 .8540 -.2744 .0891 Uiso calc 1.0
H13c -.0519 .9204 -.2993 .0891 Uiso calc 1.0
H14a -.0652 .6345 .1183 .0770 Uiso calc 1.0
H14b -.1185 .5075 .3002 .0770 Uiso calc 1.0
H15a .4243 .0203 -.1012 .1051 Uiso calc 1.0
H15b .5471 .0221 .0442 .1051 Uiso calc 1.0
H15c .4755 -.1632 .0430 .1051 Uiso calc 1.0
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
C4 O1 C5A 61.34(8) yes
C6 O2 C12 109.70(10) no
O5A O4A C1 104.90(10) yes
O4A O5A H5O 92(2) yes
O4A C1 C2 100.6(2) yes
O4A C1 C10 109.6(2) yes
C2 C1 C10 119.7(2) no
C2 C1 O4B 124.4(5) no
C10 C1 O4B 113.6(6) no
C1 C2 C3 117.2(2) no
C2 C3 C4 114.4(2) no
O1 C4 C3 114.80(10) no
O1 C4 C5 58.70(10) yes
O1 C4 C15 112.2(2) no
C3 C4 C5 117.4(2) no
C3 C4 C15 116.8(2) no
C5 C4 C15 122.3(2) no
O1 C5 C4 60.01(9) yes
O1 C5 C6 120.50(10) no
C4 C5 C6 124.10(10) no
O2 C6 C5 109.20(10) no
O2 C6 C7 103.30(10) no
C5 C6 C7 112.60(10) no
C6 C7 C8 117.60(10) no
C6 C7 C11 101.80(10) no
C8 C7 C11 115.10(10) no
C7 C8 C9 116.60(10) no
C8 C9 C10 117.40(10) no
C1 C10 C9 117.40(10) no
C1 C10 C14 119.0(2) no
C9 C10 C14 123.40(10) no
C7 C11 C12 101.20(10) no
C7 C11 C13 116.2(2) no
C12 C11 C13 113.4(2) no
O2 C12 O3 121.5(2) no
O2 C12 C11 111.10(10) no
O3 C12 C11 127.4(2) no
C1 O4B O5B 91.0(10) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 1.453(2) yes
O1 C5 1.433(2) yes
O2 C6 1.468(2) no
O2 C12 1.333(2) no
O3 C12 1.211(2) no
O4A O5A 1.463(3) yes
O4B O5B 1.54(2) yes
O4A C1 1.458(3) yes
O5A H5O 1.01(4) yes
C1 C2 1.517(3) no
C1 C10 1.518(2) no
C1 O4B 1.43(2) no
C2 C3 1.540(4) no
C3 C4 1.514(3) no
C4 C5 1.473(2) yes
C4 C15 1.502(3) no
C5 C6 1.488(2) no
C6 C7 1.529(2) no
C7 C8 1.522(3) no
C7 C11 1.528(2) no
C8 C9 1.531(2) no
C9 C10 1.503(2) no
C10 C14 1.317(2) yes
C11 C12 1.511(3) no
C11 C13 1.507(3) yes
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 O1 C4 C3 108.2(2) ?
C5 O1 C4 C15 -115.3(2) ?
C4 O1 C5 C6 114.3(2) ?
C12 O2 C6 C5 143.7(2) ?
C12 O2 C6 C7 23.6(2) y
C6 O2 C12 O3 178.7(2) ?
C6 O2 C12 C11 -2.1(2) y
C1 O4A O5A H5O -158(2) ?
O4A C1 C2 C3 -178.0(2) ?
C10 C1 C2 C3 -58.0(3) ?
O4B C1 C2 C3 140.3(8) ?
O4A C1 C10 C9 66.3(2) ?
O4A C1 C10 C14 -108.0(2) ?
C2 C1 C10 C9 -49.0(2) y
C2 C1 C10 C14 136.6(2) ?
O4B C1 C10 C9 114.5(7) ?
O4B C1 C10 C14 -59.8(7) ?
C2 C1 O4B O5B 80.0(10) ?
C10 C1 O4B O5B -83.0(10) ?
C1 C2 C3 C4 85.1(2) y
C2 C3 C4 O1 -164.2(2) ?
C2 C3 C4 C5 -98.2(2) y
C2 C3 C4 C15 61.4(2) ?
O1 C4 C5 C6 -108.5(2) ?
C3 C4 C5 O1 -103.7(2) ?
C3 C4 C5 C6 147.8(2) y
C15 C4 C5 O1 98.0(2) ?
C15 C4 C5 C6 -10.5(3) ?
O1 C5 C6 O2 60.3(2) ?
O1 C5 C6 C7 174.42(12) ?
C4 C5 C6 O2 132.7(2) ?
C4 C5 C6 C7 -113.2(2) y
O2 C6 C7 C8 -161.35(13) ?
O2 C6 C7 C11 -34.7(2) y
C5 C6 C7 C8 81.0(2) y
C5 C6 C7 C11 -152.30(10) ?
C6 C7 C8 C9 -54.8(2) y
C11 C7 C8 C9 -174.68(14) ?
C6 C7 C11 C12 32.5(2) ?
C6 C7 C11 C13 155.9(2) ?
C8 C7 C11 C12 160.82(14) ?
C8 C7 C11 C13 -75.8(2) ?
C7 C8 C9 C10 -54.5(2) y
C8 C9 C10 C1 163.8(2) y
C8 C9 C10 C14 -22.1(3) y
C7 C11 C12 O2 -20.1(2) y
C7 C11 C12 O3 159.1(2) y
C13 C11 C12 O2 -145.3(2) ?
C13 C11 C12 O3 33.8(3) ?
