#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/91/2009142.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_2009142
loop_
_publ_author_name
'González-Platas, Javier'
'Ruiz-Pérez, Catalina'
'González, Antonio G.'
'Bermejo, Jaime'
'Medjroubi, Kamel'
_publ_section_title
;
 4β,15-Dihydro-3-dehydrosolstitialin A
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1837
_journal_page_last               1839
_journal_paper_doi               10.1107/S010827019900918X
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C15 H20 O5'
_chemical_formula_weight         280.31
_chemical_name_systematic
;
3-hydroxy-3-hydroxymethyl-9-methyl-6-methyleneperhydroazuleno[4,5-b]furan-
2,8-dione
;
_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           'form.cif (version 2.0)'
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   8.7620(10)
_cell_length_b                   9.596(2)
_cell_length_c                   16.363(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.41
_cell_measurement_theta_min      11.97
_cell_volume                     1375.8(4)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1994)'
_computing_data_reduction        'XCAD-4 (Harms, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.011
_diffrn_reflns_av_sigmaI/netI    0.020
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            2334
_diffrn_reflns_theta_full        29.96
_diffrn_reflns_theta_max         29.96
_diffrn_reflns_theta_min         2.46
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         2289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.045
_refine_ls_R_factor_gt           0.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0651P)²+0.0897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.098
_reflns_number_gt                2017
_reflns_number_total             2289
_reflns_threshold_expression     'I > 2 σ(I)'
_cod_data_source_file            jz1363.cif
_cod_data_source_block           global
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2009142
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
O1 .2318(3) 1.1841(3) -.07127(12) .0809(6) Uani d . 1 . . O
O2 .48130(13) .76887(13) .11345(7) .0329(3) Uani d . 1 . . O
O3 .66182(15) .65501(17) .18198(9) .0468(3) Uani d . 1 . . O
O4 .47868(15) .72352(13) .32021(7) .0340(3) Uani d . 1 . . O
O5 .32613(19) .48073(14) .17033(9) .0477(3) Uani d . 1 . . O
C1 .1530(2) 1.02940(17) .12643(10) .0339(3) Uani d . 1 . . C
C2 .1346(3) 1.1513(2) .06600(15) .0516(5) Uani d . 1 . . C
C3 .2220(3) 1.1138(2) -.00943(13) .0481(5) Uani d . 1 . . C
C4 .3051(2) .9772(2) .00279(11) .0395(4) Uani d . 1 . . C
C5 .30336(19) .95889(16) .09603(9) .0279(3) Uani d . 1 . . C
C6 .32125(17) .80927(16) .12457(9) .0253(3) Uani d . 1 . . C
C7 .28610(17) .78676(15) .21603(8) .0238(3) Uani d . 1 . . C
C8 .12122(18) .74161(17) .23014(10) .0309(3) Uani d . 1 . . C
C9 .0029(2) .8558(2) .21348(12) .0382(4) Uani d . 1 . . C
C10 .01792(19) .93080(17) .13226(11) .0343(3) Uani d . 1 . . C
C11 .41042(16) .68475(15) .24422(8) .0245(3) Uani d . 1 . . C
C12 .53406(18) .69924(16) .17854(10) .0292(3) Uani d . 1 . . C
C13 .3654(2) .53117(16) .24893(11) .0331(3) Uani d . 1 . . C
C14 -.0841(3) .9131(3) .07354(15) .0501(5) Uani d . 1 . . C
C15 .4604(4) .9730(3) -.03837(15) .0623(7) Uani d . 1 . . C
H1 .173(3) 1.063(2) .1812(14) .043(6) Uiso d . 1 . . H
H21 .021(4) 1.171(3) .0509(16) .065(8) Uiso d . 1 . . H
H22 .175(3) 1.241(3) .0938(17) .066(8) Uiso d . 1 . . H
H4 .246(3) .907(3) -.0208(13) .040(6) Uiso d . 1 . . H
H5 .383(2) 1.009(2) .1186(12) .027(5) Uiso d . 1 . . H
H6 .260(2) .746(2) .0921(12) .031(5) Uiso d . 1 . . H
H7 .313(3) .874(2) .2472(12) .029(5) Uiso d . 1 . . H
H81 .111(3) .710(2) .2854(14) .039(6) Uiso d . 1 . . H
H82 .098(3) .664(3) .1981(14) .046(6) Uiso d . 1 . . H
H91 -.093(3) .812(3) .2157(16) .055(7) Uiso d . 1 . . H
H92 .019(3) .928(3) .2592(17) .049(6) Uiso d . 1 . . H
H131 .450(3) .477(3) .2719(14) .049(6) Uiso d . 1 . . H
H132 .277(3) .523(3) .2872(14) .050(7) Uiso d . 1 . . H
H141 -.079(3) .956(3) .0254(17) .054(7) Uiso d . 1 . . H
H142 -.169(3) .856(3) .0801(16) .057(7) Uiso d . 1 . . H
H151 .533(4) 1.038(3) -.0114(18) .067(9) Uiso d . 1 . . H
H152 .457(4) .993(3) -.1004(19) .077(9) Uiso d . 1 . . H
H153 .509(5) .871(4) -.036(2) .093(11) Uiso d . 1 . . H
H4W .403(4) .733(3) .3574(17) .070(9) Uiso d . 1 . . H
H5W .382(4) .409(3) .1625(18) .070(9) Uiso d . 1 . . H
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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-3 -3 -6
-4 0 6
-4 6 -7
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
C12 O2 C6 111.31(12) yes
C11 O4 H4W 107.9(19) ?
C13 O5 H5W 106(2) ?
C10 C1 C2 115.57(16) ?
C10 C1 C5 114.05(13) ?
C2 C1 C5 102.30(15) ?
C10 C1 H1 107.0(15) ?
C2 C1 H1 111.1(14) ?
C5 C1 H1 106.5(15) ?
C3 C2 C1 107.07(17) ?
C3 C2 H21 109.7(15) ?
C1 C2 H21 112.9(16) ?
C3 C2 H22 112.8(16) ?
C1 C2 H22 108.2(15) ?
H21 C2 H22 106(2) ?
O1 C3 C2 126.0(2) yes
O1 C3 C4 123.7(2) yes
C2 C3 C4 110.21(15) ?
C3 C4 C15 113.31(17) ?
C3 C4 C5 103.04(17) ?
C15 C4 C5 116.51(18) ?
C3 C4 H4 107.9(15) ?
C15 C4 H4 106.9(14) ?
C5 C4 H4 108.8(14) ?
C6 C5 C4 114.39(14) ?
C6 C5 C1 113.50(13) ?
C4 C5 C1 105.98(14) ?
C6 C5 H5 106.9(12) ?
C4 C5 H5 109.4(12) ?
C1 C5 H5 106.5(12) ?
O2 C6 C5 108.10(12) yes
O2 C6 C7 105.91(11) yes
C5 C6 C7 114.22(12) ?
O2 C6 H6 107.4(12) ?
C5 C6 H6 111.4(12) ?
C7 C6 H6 109.5(11) ?
C8 C7 C11 116.44(12) ?
C8 C7 C6 112.05(12) ?
C11 C7 C6 103.82(11) ?
C8 C7 H7 112.3(13) ?
C11 C7 H7 102.4(12) ?
C6 C7 H7 109.1(12) ?
C7 C8 C9 114.24(14) ?
C7 C8 H81 108.9(14) ?
C9 C8 H81 109.2(14) ?
C7 C8 H82 110.3(16) ?
C9 C8 H82 109.0(16) ?
H81 C8 H82 105(2) ?
C10 C9 C8 115.88(14) ?
C10 C9 H91 108.9(16) ?
C8 C9 H91 106.2(18) ?
C10 C9 H92 107.8(15) ?
C8 C9 H92 105.0(15) ?
H91 C9 H92 113(2) ?
C14 C10 C1 124.15(18) ?
C14 C10 C9 121.09(19) ?
C1 C10 C9 114.72(15) ?
O4 C11 C13 108.38(12) yes
O4 C11 C12 106.90(13) yes
C13 C11 C12 107.79(13) ?
O4 C11 C7 113.10(12) yes
C13 C11 C7 116.55(12) ?
C12 C11 C7 103.48(12) ?
O3 C12 O2 122.43(15) yes
O3 C12 C11 126.54(16) yes
O2 C12 C11 111.03(13) yes
O5 C13 C11 110.28(13) yes
O5 C13 H131 110.4(14) ?
C11 C13 H131 109.8(15) ?
O5 C13 H132 110.7(14) ?
C11 C13 H132 108.1(16) ?
H131 C13 H132 107.5(19) ?
C10 C14 H141 123.2(19) ?
C10 C14 H142 122.1(17) ?
H141 C14 H142 115(2) ?
C4 C15 H151 111.0(18) ?
C4 C15 H152 114.1(19) ?
H151 C15 H152 110(3) ?
C4 C15 H153 111(2) ?
H151 C15 H153 108(3) ?
H152 C15 H153 102(2) ?
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 C3 . 1.219(2) yes
O2 C12 . 1.340(2) yes
O2 C6 . 1.4663(18) yes
O3 C12 . 1.199(2) yes
O4 C11 . 1.4292(17) yes
O4 H4W . .90(3) ?
O5 C13 . 1.417(2) yes
O5 H5W . .85(3) ?
C1 C10 . 1.519(2) ?
C1 C2 . 1.540(3) ?
C1 C5 . 1.562(2) ?
C1 H1 . .97(2) ?
C2 C3 . 1.497(4) ?
C2 H21 . 1.05(3) ?
C2 H22 . 1.04(3) ?
C3 C4 . 1.513(3) ?
C4 C15 . 1.519(3) ?
C4 C5 . 1.536(2) ?
C4 H4 . .93(3) ?
C5 C6 . 1.518(2) ?
C5 H5 . .92(2) ?
C6 C7 . 1.5432(19) ?
C6 H6 . .97(2) ?
C7 C8 . 1.526(2) ?
C7 C11 . 1.535(2) ?
C7 H7 . 1.01(2) ?
C8 C9 . 1.532(2) ?
C8 H81 . .96(2) ?
C8 H82 . .94(3) ?
C9 C10 . 1.517(2) ?
C9 H91 . .94(3) ?
C9 H92 . 1.03(3) ?
C10 C14 . 1.324(3) ?
C11 C13 . 1.528(2) ?
C11 C12 . 1.532(2) ?
C13 H131 . .98(3) ?
C13 H132 . 1.00(3) ?
C14 H141 . .89(3) ?
C14 H142 . .93(3) ?
C15 H151 . .99(3) ?
C15 H152 . 1.03(3) ?
C15 H153 . 1.07(4) ?
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
_geom_hbond_publ_flag
O4 H4W O1 2_575 0.90(3) 1.84(3) 2.709(3) 160(3) yes
O5 H5W O4 4_645 0.85(3) 2.18(3) 3.007(2) 164(3) yes
C5 H5 O4 4_655 0.924(18) 2.590(19) 3.460(2) 157.1(15) no
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
C10 C1 C2 C3 -101.7(2)
C5 C1 C2 C3 22.8(2)
C1 C2 C3 O1 178.7(2)
C1 C2 C3 C4 -4.1(2)
O1 C3 C4 C15 33.6(3)
C2 C3 C4 C15 -143.6(2)
O1 C3 C4 C5 160.4(2)
C2 C3 C4 C5 -16.9(2)
C3 C4 C5 C6 157.01(15)
C15 C4 C5 C6 -78.3(2)
C3 C4 C5 C1 31.19(19)
C15 C4 C5 C1 155.90(18)
C10 C1 C5 C6 -34.44(19)
C2 C1 C5 C6 -159.96(15)
C10 C1 C5 C4 91.92(17)
C2 C1 C5 C4 -33.61(18)
C12 O2 C6 C5 136.20(13)
C12 O2 C6 C7 13.38(16)
C4 C5 C6 O2 74.54(17)
C1 C5 C6 O2 -163.68(12)
C4 C5 C6 C7 -167.86(14)
C1 C5 C6 C7 -46.08(17)
O2 C6 C7 C8 -146.85(12)
C5 C6 C7 C8 94.30(15)
O2 C6 C7 C11 -20.38(14)
C5 C6 C7 C11 -139.23(13)
C11 C7 C8 C9 170.89(13)
C6 C7 C8 C9 -69.81(18)
C7 C8 C9 C10 49.9(2)
C2 C1 C10 C14 24.1(3)
C5 C1 C10 C14 -94.1(2)
C2 C1 C10 C9 -153.49(17)
C5 C1 C10 C9 88.34(17)
C8 C9 C10 C14 110.4(2)
C8 C9 C10 C1 -71.9(2)
C8 C7 C11 O4 -101.47(15)
C6 C7 C11 O4 134.87(12)
C8 C7 C11 C13 25.13(19)
C6 C7 C11 C13 -98.52(14)
C8 C7 C11 C12 143.23(13)
C6 C7 C11 C12 19.58(14)
C6 O2 C12 O3 179.11(16)
C6 O2 C12 C11 -0.35(17)
O4 C11 C12 O3 48.2(2)
C13 C11 C12 O3 -68.2(2)
C7 C11 C12 O3 167.81(17)
O4 C11 C12 O2 -132.39(13)
C13 C11 C12 O2 111.28(14)
C7 C11 C12 O2 -12.75(16)
O4 C11 C13 O5 -168.18(14)
C12 C11 C13 O5 -52.81(17)
C7 C11 C13 O5 62.91(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21182780
