#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/42/2224265.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_2224265
loop_
_publ_author_name
'Gille, Annika'
'Schürmann, Markus'
'Preut, Hans'
'Hiersemann, Martin'
_publ_section_title
(3R,4R,5S)-4-Hydroxy-3-methyl-5-[(2S,3R)-3-methylpent-4-en-2-yl]-4,5-dihydrofuran-2(3H)-one
_journal_coeditor_code           HB5238
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3274
_journal_paper_doi               10.1107/S1600536809050399
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H18 O3'
_chemical_formula_moiety         'C11 H18 O3'
_chemical_formula_sum            'C11 H18 O3'
_chemical_formula_weight         198.25
_chemical_name_systematic
;(3R,4R,5S)-4-Hydroxy-3-methyl-5-[(2S,3R)-3-
methylpent-4-en-2-yl]-4,5-dihydrofuran-2(3H)-one
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 92.563(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.7265(10)
_cell_length_b                   6.4798(8)
_cell_length_c                   11.0598(16)
_cell_measurement_reflns_used    1159
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.06
_cell_measurement_theta_min      2.64
_cell_volume                     553.17(13)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0560
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur S CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3255
_diffrn_reflns_theta_full        25.48
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_min         2.64
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1129
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0349
_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)+(0.0110P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0465
_refine_ls_wR_factor_ref         0.0481
_reflns_number_gt                737
_reflns_number_total             1129
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5238.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2224265
_cod_database_fobs_code          2224265
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.2173(2) 0.1438(2) 0.07628(15) 0.0251(5) Uani d . 1 . .
O O2 0.2731(2) 0.0175(3) -0.10413(17) 0.0328(6) Uani d . 1 . .
O O3 0.1599(2) 0.6838(3) 0.05289(17) 0.0370(6) Uani d . 1 . .
H H3 0.2032 0.7730 0.0082 0.056 Uiso calc R 1 . .
C C1 0.2453(3) 0.1658(5) -0.0428(2) 0.0267(8) Uani d . 1 . .
C C2 0.2329(4) 0.3900(4) -0.0771(2) 0.0251(8) Uani d . 1 . .
H H2 0.1128 0.4168 -0.1109 0.030 Uiso calc R 1 . .
C C3 0.2533(3) 0.4969(4) 0.0446(2) 0.0275(8) Uani d . 1 . .
H H3A 0.3790 0.5230 0.0645 0.033 Uiso calc R 1 . .
C C4 0.1847(4) 0.3431(4) 0.1331(3) 0.0251(7) Uani d . 1 . .
H H4 0.0569 0.3630 0.1382 0.030 Uiso calc R 1 . .
C C5 0.2674(4) 0.3375(4) 0.2598(2) 0.0293(8) Uani d . 1 . .
H H5 0.3954 0.3280 0.2512 0.035 Uiso calc R 1 . .
C C6 0.2135(4) 0.1458(4) 0.3322(2) 0.0314(8) Uani d . 1 . .
H H6 0.2292 0.0238 0.2784 0.038 Uiso calc R 1 . .
C C7 0.3345(4) 0.1158(5) 0.4405(3) 0.0409(9) Uani d . 1 . .
H H7 0.4546 0.1147 0.4255 0.049 Uiso calc R 1 . .
C C8 0.2950(4) 0.0912(5) 0.5523(2) 0.0487(10) Uani d . 1 . .
H H8A 0.1770 0.0910 0.5730 0.058 Uiso calc R 1 . .
H H8B 0.3841 0.0735 0.6134 0.058 Uiso calc R 1 . .
C C9 0.3607(3) 0.4531(4) -0.1730(2) 0.0350(9) Uani d . 1 . .
H H9A 0.4789 0.4182 -0.1443 0.053 Uiso calc R 1 . .
H H9B 0.3523 0.6022 -0.1872 0.053 Uiso calc R 1 . .
H H9C 0.3323 0.3793 -0.2487 0.053 Uiso calc R 1 . .
C C10 0.2329(4) 0.5418(4) 0.3243(2) 0.0401(9) Uani d . 1 . .
H H10A 0.2922 0.6541 0.2836 0.060 Uiso calc R 1 . .
H H10B 0.2765 0.5329 0.4087 0.060 Uiso calc R 1 . .
H H10C 0.1080 0.5689 0.3218 0.060 Uiso calc R 1 . .
C C11 0.0231(3) 0.1493(5) 0.3622(2) 0.0434(9) Uani d . 1 . .
H H11A -0.0082 0.0167 0.3979 0.065 Uiso calc R 1 . .
H H11B -0.0484 0.1728 0.2881 0.065 Uiso calc R 1 . .
H H11C 0.0033 0.2605 0.4201 0.065 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 0.0000 '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 0.0000 '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
C1 O1 C4 . . 111.3(2) ?
C3 O3 H3 . . 109.5 ?
O2 C1 O1 . . 120.4(3) ?
O2 C1 C2 . . 129.9(2) ?
O1 C1 C2 . . 109.7(3) ?
C1 C2 C3 . . 102.4(2) ?
C1 C2 C9 . . 113.4(2) ?
C3 C2 C9 . . 116.5(2) ?
C1 C2 H2 . . 108.1 ?
C3 C2 H2 . . 108.1 ?
C9 C2 H2 . . 108.1 ?
O3 C3 C4 . . 109.1(2) ?
O3 C3 C2 . . 114.6(2) ?
C4 C3 C2 . . 104.4(2) ?
O3 C3 H3A . . 109.5 ?
C4 C3 H3A . . 109.5 ?
C2 C3 H3A . . 109.5 ?
O1 C4 C3 . . 103.4(2) ?
O1 C4 C5 . . 107.6(2) ?
C3 C4 C5 . . 118.0(2) ?
O1 C4 H4 . . 109.1 ?
C3 C4 H4 . . 109.1 ?
C5 C4 H4 . . 109.1 ?
C4 C5 C10 . . 109.6(2) ?
C4 C5 C6 . . 112.7(2) ?
C10 C5 C6 . . 113.4(2) ?
C4 C5 H5 . . 106.9 ?
C10 C5 H5 . . 106.9 ?
C6 C5 H5 . . 106.9 ?
C7 C6 C11 . . 113.6(2) ?
C7 C6 C5 . . 110.2(2) ?
C11 C6 C5 . . 112.7(2) ?
C7 C6 H6 . . 106.6 ?
C11 C6 H6 . . 106.6 ?
C5 C6 H6 . . 106.6 ?
C8 C7 C6 . . 127.8(3) ?
C8 C7 H7 . . 116.1 ?
C6 C7 H7 . . 116.1 ?
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_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 . 1.352(3) ?
O1 C4 . 1.463(3) ?
O2 C1 . 1.201(3) ?
O3 C3 . 1.415(3) ?
O3 H3 . 0.8400 ?
C1 C2 . 1.504(4) ?
C2 C3 . 1.516(3) ?
C2 C9 . 1.536(3) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.510(3) ?
C3 H3A . 1.0000 ?
C4 C5 . 1.515(3) ?
C4 H4 . 1.0000 ?
C5 C10 . 1.533(3) ?
C5 C6 . 1.544(4) ?
C5 H5 . 1.0000 ?
C6 C7 . 1.499(3) ?
C6 C11 . 1.523(3) ?
C6 H6 . 1.0000 ?
C7 C8 . 1.296(3) ?
C7 H7 . 0.9500 ?
C8 H8A . 0.9500 ?
C8 H8B . 0.9500 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
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 O1 1_565 0.84 2.52 3.023(2) 120
O3 H3 O2 1_565 0.84 2.10 2.931(3) 171
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 . . . . -179.5(2) ?
C4 O1 C1 C2 . . . . -0.1(3) ?
O2 C1 C2 C3 . . . . -162.7(3) ?
O1 C1 C2 C3 . . . . 18.0(3) ?
O2 C1 C2 C9 . . . . -36.3(4) ?
O1 C1 C2 C9 . . . . 144.4(2) ?
C1 C2 C3 O3 . . . . -147.4(2) ?
C9 C2 C3 O3 . . . . 88.3(3) ?
C1 C2 C3 C4 . . . . -28.1(3) ?
C9 C2 C3 C4 . . . . -152.4(2) ?
C1 O1 C4 C3 . . . . -18.0(3) ?
C1 O1 C4 C5 . . . . -143.6(2) ?
O3 C3 C4 O1 . . . . 151.2(2) ?
C2 C3 C4 O1 . . . . 28.3(3) ?
O3 C3 C4 C5 . . . . -90.1(3) ?
C2 C3 C4 C5 . . . . 147.0(2) ?
O1 C4 C5 C10 . . . . -178.7(2) ?
C3 C4 C5 C10 . . . . 64.9(3) ?
O1 C4 C5 C6 . . . . -51.4(3) ?
C3 C4 C5 C6 . . . . -167.8(2) ?
C4 C5 C6 C7 . . . . 163.9(2) ?
C10 C5 C6 C7 . . . . -70.9(3) ?
C4 C5 C6 C11 . . . . -68.0(3) ?
C10 C5 C6 C11 . . . . 57.3(3) ?
C11 C6 C7 C8 . . . . 0.8(5) ?
C5 C6 C7 C8 . . . . 128.5(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743974
