##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(3S,4S,5S)-4-Hydroxy-3-methyl-5-[(2S,3R)-3-
methylpent-4-en-2-yl]-4,5-dihydrofuran-2(3H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H18 O3'
_chemical_formula_sum     'C11 H18 O3'
_chemical_formula_weight     198.25
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     5.4414(14)
_cell_length_b     10.132(2)
_cell_length_c     20.975(8)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1156.4(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     7554
_cell_measurement_theta_min     2.80
_cell_measurement_theta_max     25.01
_cell_measurement_temperature     291.0(10)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.06
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.139
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     432
_exptl_absorpt_coefficient_mu     0.081
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     291.0(10)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD'
_diffrn_measurement_method
;
111 frames via ω-rotation (Δω=2%) and two times 180 s per frame
(three sets at different κ-angles)
;
_diffrn_detector_area_resol_mean     '19 vertical, 18 horizontal'
_diffrn_reflns_number     7554
_diffrn_reflns_av_R_equivalents     0.048
_diffrn_reflns_av_sigmaI/netI     0.2829
_diffrn_reflns_theta_min     2.80
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     24
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     1223
_reflns_number_gt     346
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1959
_refine_ls_R_factor_gt     0.0364
_refine_ls_wR_factor_gt     0.0570
_refine_ls_wR_factor_ref     0.0871
_refine_ls_goodness_of_fit_ref     0.971
_refine_ls_restrained_S_all     0.971
_refine_ls_number_reflns     1223
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
; calc
 [1.0 exp(5.65(sinθ/λ)²)]/[σ²(Fo²)]
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.007
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.087
_refine_diff_density_min     -0.133
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
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'
_computing_data_collection     'COLLECT (Nonius, 1998)'
_computing_cell_refinement
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_data_reduction
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003)
;
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 0.1778(7) 0.0092(4) -0.3153(2) 0.0647(11) Uani d . 1 . .
    O O2 0.4408(8) 0.0462(4) -0.2370(2) 0.0971(19) Uani d . 1 . .
    O O3 0.3095(10) -0.2710(5) -0.3391(2) 0.0890(15) Uani d . 1 . .
    H H3 0.4090 -0.3080 -0.3158 0.133 Uiso calc R 1 . .
    C C1 0.2948(12) -0.0261(7) -0.2615(3) 0.075(2) Uani d . 1 . .
    C C2 0.2076(11) -0.1595(6) -0.2396(3) 0.0641(19) Uani d . 1 . .
    H H2A 0.3449 -0.2114 -0.2227 0.077 Uiso calc R 1 . .
    C C3 0.1142(11) -0.2191(6) -0.3017(3) 0.0635(19) Uani d . 1 . .
    H H3B -0.0147 -0.2849 -0.2942 0.076 Uiso calc R 1 . .
    C C4 0.0156(11) -0.0982(5) -0.3372(3) 0.0596(18) Uani d . 1 . .
    H H4A -0.1522 -0.0803 -0.3227 0.072 Uiso calc R 1 . .
    C C5 0.0176(10) -0.1020(6) -0.4090(3) 0.0578(17) Uani d . 1 . .
    H H5A 0.1854 -0.1235 -0.4225 0.069 Uiso calc R 1 . .
    C C6 -0.0502(11) 0.0338(6) -0.4390(3) 0.069(2) Uani d . 1 . .
    H H6A 0.0627 0.0986 -0.4205 0.082 Uiso calc R 1 . .
    C C7 0.0064(15) 0.0286(7) -0.5094(4) 0.107(3) Uani d . 1 . .
    H H7A 0.1591 -0.0070 -0.5193 0.129 Uiso calc R 1 . .
    C C8 -0.1131(18) 0.0629(9) -0.5549(4) 0.170(4) Uani d . 1 . .
    H H8A -0.2681 0.0996 -0.5491 0.205 Uiso calc R 1 . .
    H H8B -0.0501 0.0527 -0.5958 0.205 Uiso calc R 1 . .
    C C9 0.0066(12) -0.1412(5) -0.1883(3) 0.093(2) Uani d . 1 . .
    H H9A -0.0491 -0.2261 -0.1740 0.140 Uiso calc R 1 . .
    H H9B -0.1291 -0.0932 -0.2062 0.140 Uiso calc R 1 . .
    H H9C 0.0731 -0.0929 -0.1529 0.140 Uiso calc R 1 . .
    C C10 -0.1534(11) -0.2165(5) -0.4322(3) 0.085(2) Uani d . 1 . .
    H H10A -0.0821 -0.2998 -0.4207 0.128 Uiso calc R 1 . .
    H H10B -0.1712 -0.2119 -0.4777 0.128 Uiso calc R 1 . .
    H H10C -0.3118 -0.2079 -0.4125 0.128 Uiso calc R 1 . .
    C C11 -0.3096(12) 0.0798(6) -0.4222(3) 0.102(3) Uani d . 1 . .
    H H11A -0.3376 0.1657 -0.4401 0.152 Uiso calc R 1 . .
    H H11B -0.3269 0.0840 -0.3767 0.152 Uiso calc R 1 . .
    H H11C -0.4273 0.0187 -0.4393 0.152 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.064(3) 0.056(3) 0.074(3) -0.002(3) -0.011(3) -0.006(2)
    O2 0.091(4) 0.110(4) 0.091(4) -0.027(3) -0.026(3) -0.012(3)
    O3 0.105(4) 0.080(3) 0.083(3) 0.034(3) 0.005(3) 0.002(3)
    C1 0.062(6) 0.083(6) 0.081(6) 0.010(5) -0.004(5) -0.010(5)
    C2 0.073(5) 0.065(5) 0.054(5) 0.008(4) -0.013(4) 0.009(3)
    C3 0.072(5) 0.048(4) 0.071(5) 0.000(4) 0.009(4) 0.005(4)
    C4 0.053(5) 0.056(4) 0.070(5) 0.000(4) 0.002(4) -0.006(4)
    C5 0.039(4) 0.068(4) 0.066(5) 0.001(4) -0.002(4) -0.008(4)
    C6 0.072(6) 0.073(4) 0.061(5) 0.005(4) -0.013(4) 0.009(4)
    C7 0.133(7) 0.106(6) 0.082(7) 0.050(6) -0.028(6) 0.007(5)
    C8 0.233(13) 0.159(9) 0.119(10) -0.006(8) -0.019(9) 0.019(7)
    C9 0.119(7) 0.089(5) 0.071(6) 0.002(5) 0.021(6) 0.004(4)
    C10 0.094(6) 0.078(5) 0.084(5) -0.016(4) -0.015(5) -0.013(4)
    C11 0.085(6) 0.111(6) 0.109(6) 0.048(5) 0.007(5) 0.021(4)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 C1 . 1.344(6) ?
    O1 C4 . 1.475(6) ?
    O2 C1 . 1.196(6) ?
    O3 C3 . 1.422(6) ?
    O3 H3 . 0.8200 ?
    C1 C2 . 1.504(7) ?
    C2 C3 . 1.523(7) ?
    C2 C9 . 1.546(7) ?
    C2 H2A . 0.9800 ?
    C3 C4 . 1.531(6) ?
    C3 H3B . 0.9800 ?
    C4 C5 . 1.506(6) ?
    C4 H4A . 0.9800 ?
    C5 C6 . 1.557(6) ?
    C5 C10 . 1.564(7) ?
    C5 H5A . 0.9800 ?
    C6 C7 . 1.508(8) ?
    C6 C11 . 1.527(6) ?
    C6 H6A . 0.9800 ?
    C7 C8 . 1.207(8) ?
    C7 H7A . 0.9300 ?
    C8 H8A . 0.9300 ?
    C8 H8B . 0.9300 ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
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
    C1 O1 C4 . . 110.5(5) ?
    C3 O3 H3 . . 109.5 ?
    O2 C1 O1 . . 120.8(7) ?
    O2 C1 C2 . . 129.0(7) ?
    O1 C1 C2 . . 110.2(6) ?
    C1 C2 C3 . . 101.6(5) ?
    C1 C2 C9 . . 109.1(5) ?
    C3 C2 C9 . . 114.0(6) ?
    C1 C2 H2A . . 110.6 ?
    C3 C2 H2A . . 110.6 ?
    C9 C2 H2A . . 110.6 ?
    O3 C3 C2 . . 111.7(5) ?
    O3 C3 C4 . . 106.8(5) ?
    C2 C3 C4 . . 102.5(5) ?
    O3 C3 H3B . . 111.8 ?
    C2 C3 H3B . . 111.8 ?
    C4 C3 H3B . . 111.8 ?
    O1 C4 C5 . . 109.1(5) ?
    O1 C4 C3 . . 103.2(4) ?
    C5 C4 C3 . . 117.6(5) ?
    O1 C4 H4A . . 108.8 ?
    C5 C4 H4A . . 108.8 ?
    C3 C4 H4A . . 108.8 ?
    C4 C5 C6 . . 112.3(5) ?
    C4 C5 C10 . . 109.0(5) ?
    C6 C5 C10 . . 112.8(5) ?
    C4 C5 H5A . . 107.5 ?
    C6 C5 H5A . . 107.5 ?
    C10 C5 H5A . . 107.5 ?
    C7 C6 C11 . . 115.1(5) ?
    C7 C6 C5 . . 108.4(5) ?
    C11 C6 C5 . . 113.3(5) ?
    C7 C6 H6A . . 106.5 ?
    C11 C6 H6A . . 106.5 ?
    C5 C6 H6A . . 106.5 ?
    C8 C7 C6 . . 130.9(9) ?
    C8 C7 H7A . . 114.6 ?
    C6 C7 H7A . . 114.6 ?
    C7 C8 H8A . . 120.0 ?
    C7 C8 H8B . . 120.0 ?
    H8A C8 H8B . . 120.0 ?
    C2 C9 H9A . . 109.5 ?
    C2 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C2 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C5 C10 H10A . . 109.5 ?
    C5 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C5 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C6 C11 H11A . . 109.5 ?
    C6 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C6 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
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
    C4 O1 C1 O2 . . . . 177.8(6) ?
    C4 O1 C1 C2 . . . . -3.8(7) ?
    O2 C1 C2 C3 . . . . -157.8(7) ?
    O1 C1 C2 C3 . . . . 24.0(7) ?
    O2 C1 C2 C9 . . . . 81.5(9) ?
    O1 C1 C2 C9 . . . . -96.7(6) ?
    C1 C2 C3 O3 . . . . 80.8(6) ?
    C9 C2 C3 O3 . . . . -162.0(5) ?
    C1 C2 C3 C4 . . . . -33.2(6) ?
    C9 C2 C3 C4 . . . . 84.0(6) ?
    C1 O1 C4 C5 . . . . -143.8(5) ?
    C1 O1 C4 C3 . . . . -18.0(6) ?
    O3 C3 C4 O1 . . . . -85.8(5) ?
    C2 C3 C4 O1 . . . . 31.7(6) ?
    O3 C3 C4 C5 . . . . 34.3(8) ?
    C2 C3 C4 C5 . . . . 151.8(5) ?
    O1 C4 C5 C6 . . . . -54.5(6) ?
    C3 C4 C5 C6 . . . . -171.5(5) ?
    O1 C4 C5 C10 . . . . 179.7(5) ?
    C3 C4 C5 C10 . . . . 62.7(7) ?
    C4 C5 C6 C7 . . . . 168.6(6) ?
    C10 C5 C6 C7 . . . . -67.7(7) ?
    C4 C5 C6 C11 . . . . -62.3(7) ?
    C10 C5 C6 C11 . . . . 61.4(7) ?
    C11 C6 C7 C8 . . . . 5.6(14) ?
    C5 C6 C7 C8 . . . . 133.7(11) ?
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
    O3 H3 O2 3_644 0.82 2.02 2.798(6) 158.2
data_global
_journal_date_recd_electronic     2008-08-11
_journal_date_accepted     2008-08-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      9
_journal_page_first     o1835
_journal_page_last     o1835
_journal_paper_category     QO
_journal_coeditor_code     BT2768
_publ_contact_author_name     'Dr. Hans Preut'
_publ_contact_author_address
;       Fachbereich Chemie
 Technische Universität Dortmund
 Otto-Hahn-Str. 6
 44221 Dortmund
 Germany
;
_publ_contact_author_email     'hans.preut@udo.edu'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '49-231-755-3813'
_publ_section_title
;\
(3S,4S,5S)-4-Hydroxy-3-methyl-5-[(2S,3R)-3-\
methylpent-4-en-2-yl]-4,5-dihydrofuran-2(3H)-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Gille, Annika' .
;      Fakultät Chemie
       Technische Universität Dortmund
       Otto-Hahn-Str. 6
       44221 Dortmund
       Germany
;
    'Schürmann, Markus' .
;      Fakultät  Chemie
       Technische Universität Dortmund
       Otto-Hahn-Str. 6
       44221 Dortmund
       Germany
;
    'Preut, Hans' .
;      Fakultät  Chemie
       Technische Universität Dortmund
       Otto-Hahn-Str. 6
       44221 Dortmund
       Germany
;
    'Hiersemann, Martin' .
;      Fakultät  Chemie
       Technische Universität Dortmund
       Otto-Hahn-Str. 6
       44221 Dortmund
       Germany
;
