#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/04/2220499.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_2220499
loop_
_publ_author_name
'Gille, Annika'
'Bläser, Dieter'
'Boese, Roland'
'Preut, Hans'
'Hiersemann, Martin'
_publ_section_title
(3S,4S,5R)-4-Hydroxy-3-methyl-5-[(2S,3R)-3-methylpent-4-en-2-yl]-4,5-dihydrofuran-2(3H)-one
_journal_coeditor_code           HB2861
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o154
_journal_paper_doi               10.1107/S1600536808042414
_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
;(3S,4S,5R)-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                 91.211(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.604(2)
_cell_length_b                   6.574(2)
_cell_length_c                   11.323(4)
_cell_measurement_reflns_used    1365
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.67
_cell_volume                     565.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type
;
Siemens SMART three-axis goniometer with APEXII area-detector system
;
_diffrn_measurement_method       'Data collection strategy APEX 2/COSMO'
_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  0.1310
_diffrn_reflns_av_sigmaI/netI    0.1270
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7868
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.190
_refine_ls_extinction_coef       0.077(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1507
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0540
_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)+(0.0279P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                1076
_reflns_number_total             1507
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2861.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2220499
_cod_database_fobs_code          2220499
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 0.2255(2) 0.2085(3) 0.91883(16) 0.0351(5) Uani d . 1 . .
O O2 0.1493(2) 0.7353(3) 0.96072(16) 0.0382(5) Uani d . 1 . .
H H2 0.2076 0.8318 0.9904 0.057 Uiso calc R 1 . .
O O3 0.2839(2) 0.0670(3) 1.09375(17) 0.0408(5) Uani d . 1 . .
C C1 0.3186(5) 0.7143(7) 0.4846(3) 0.0700(11) Uani d . 1 . .
H H1A 0.1994 0.7345 0.4607 0.084 Uiso calc R 1 . .
H H1B 0.4096 0.7302 0.4292 0.084 Uiso calc R 1 . .
C C2 0.3570(4) 0.6651(5) 0.5929(3) 0.0471(8) Uani d . 1 . .
H H2A 0.4783 0.6469 0.6118 0.057 Uiso calc R 1 . .
C C3 0.2316(4) 0.6337(4) 0.6919(2) 0.0381(7) Uani d . 1 . .
H H3 0.2615 0.7378 0.7535 0.046 Uiso calc R 1 . .
C C4 0.2658(4) 0.4224(4) 0.7492(2) 0.0352(7) Uani d . 1 . .
H H4 0.3959 0.4082 0.7615 0.042 Uiso calc R 1 . .
C C5 0.1827(3) 0.4084(4) 0.8699(2) 0.0305(6) Uani d . 1 . .
H H5 0.0522 0.4226 0.8610 0.037 Uiso calc R 1 . .
C C6 0.2512(3) 0.5554(4) 0.9651(2) 0.0309(6) Uani d . 1 . .
H H6 0.3778 0.5877 0.9522 0.037 Uiso calc R 1 . .
C C7 0.2319(4) 0.4339(4) 1.0786(2) 0.0324(6) Uani d . 1 . .
H H7 0.1086 0.4522 1.1059 0.039 Uiso calc R 1 . .
C C8 0.2500(3) 0.2207(4) 1.0367(2) 0.0327(6) Uani d . 1 . .
C C9 0.0401(4) 0.6683(5) 0.6558(3) 0.0513(8) Uani d . 1 . .
H H9A 0.0246 0.8089 0.6288 0.077 Uiso calc R 1 . .
H H9B -0.0348 0.6434 0.7236 0.077 Uiso calc R 1 . .
H H9C 0.0072 0.5748 0.5916 0.077 Uiso calc R 1 . .
C C10 0.2046(4) 0.2460(5) 0.6698(3) 0.0468(8) Uani d . 1 . .
H H10A 0.2487 0.1173 0.7025 0.070 Uiso calc R 1 . .
H H10B 0.2503 0.2650 0.5902 0.070 Uiso calc R 1 . .
H H10C 0.0758 0.2429 0.6657 0.070 Uiso calc R 1 . .
C C11 0.3561(4) 0.4916(5) 1.1806(3) 0.0477(8) Uani d . 1 . .
H H11A 0.3352 0.4020 1.2481 0.071 Uiso calc R 1 . .
H H11B 0.3347 0.6331 1.2035 0.071 Uiso calc R 1 . .
H H11C 0.4781 0.4767 1.1558 0.071 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
C8 O1 C5 . . 110.4(2) ?
C6 O2 H2 . . 109.5 ?
C2 C1 H1A . . 120.0 ?
C2 C1 H1B . . 120.0 ?
H1A C1 H1B . . 120.0 ?
C1 C2 C3 . . 127.4(3) ?
C1 C2 H2A . . 116.3 ?
C3 C2 H2A . . 116.3 ?
C2 C3 C9 . . 113.5(2) ?
C2 C3 C4 . . 109.4(2) ?
C9 C3 C4 . . 113.4(2) ?
C2 C3 H3 . . 106.7 ?
C9 C3 H3 . . 106.7 ?
C4 C3 H3 . . 106.7 ?
C5 C4 C10 . . 110.8(2) ?
C5 C4 C3 . . 111.1(2) ?
C10 C4 C3 . . 112.7(2) ?
C5 C4 H4 . . 107.3 ?
C10 C4 H4 . . 107.3 ?
C3 C4 H4 . . 107.3 ?
O1 C5 C4 . . 107.56(19) ?
O1 C5 C6 . . 103.3(2) ?
C4 C5 C6 . . 117.0(2) ?
O1 C5 H5 . . 109.5 ?
C4 C5 H5 . . 109.5 ?
C6 C5 H5 . . 109.5 ?
O2 C6 C7 . . 113.9(2) ?
O2 C6 C5 . . 109.0(2) ?
C7 C6 C5 . . 103.1(2) ?
O2 C6 H6 . . 110.2 ?
C7 C6 H6 . . 110.2 ?
C5 C6 H6 . . 110.2 ?
C8 C7 C6 . . 102.4(2) ?
C8 C7 C11 . . 114.6(2) ?
C6 C7 C11 . . 116.1(2) ?
C8 C7 H7 . . 107.8 ?
C6 C7 H7 . . 107.8 ?
C11 C7 H7 . . 107.8 ?
O3 C8 O1 . . 119.8(3) ?
O3 C8 C7 . . 129.1(2) ?
O1 C8 C7 . . 111.1(2) ?
C3 C9 H9A . . 109.5 ?
C3 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C3 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C4 C10 H10A . . 109.5 ?
C4 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C4 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C7 C11 H11A . . 109.5 ?
C7 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C7 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 C8 . 1.347(3) ?
O1 C5 . 1.460(3) ?
O2 C6 . 1.414(3) ?
O2 H2 . 0.8400 ?
O3 C8 . 1.223(3) ?
C1 C2 . 1.296(4) ?
C1 H1A . 0.9500 ?
C1 H1B . 0.9500 ?
C2 C3 . 1.501(4) ?
C2 H2A . 0.9500 ?
C3 C9 . 1.521(4) ?
C3 C4 . 1.553(4) ?
C3 H3 . 1.0000 ?
C4 C5 . 1.520(4) ?
C4 C10 . 1.534(4) ?
C4 H4 . 1.0000 ?
C5 C6 . 1.531(4) ?
C5 H5 . 1.0000 ?
C6 C7 . 1.522(4) ?
C6 H6 . 1.0000 ?
C7 C8 . 1.487(4) ?
C7 C11 . 1.524(4) ?
C7 H7 . 1.0000 ?
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
O2 H2 O3 1_565 0.84 2.02 2.830(3) 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
C1 C2 C3 C9 . . . . -0.8(5) ?
C1 C2 C3 C4 . . . . 126.9(4) ?
C2 C3 C4 C5 . . . . 163.2(2) ?
C9 C3 C4 C5 . . . . -69.1(3) ?
C2 C3 C4 C10 . . . . -71.8(3) ?
C9 C3 C4 C10 . . . . 55.9(3) ?
C8 O1 C5 C4 . . . . 144.9(2) ?
C8 O1 C5 C6 . . . . 20.6(2) ?
C10 C4 C5 O1 . . . . 55.7(3) ?
C3 C4 C5 O1 . . . . -178.3(2) ?
C10 C4 C5 C6 . . . . 171.3(2) ?
C3 C4 C5 C6 . . . . -62.6(3) ?
O1 C5 C6 O2 . . . . -151.49(19) ?
C4 C5 C6 O2 . . . . 90.6(3) ?
O1 C5 C6 C7 . . . . -30.1(2) ?
C4 C5 C6 C7 . . . . -148.1(2) ?
O2 C6 C7 C8 . . . . 146.5(2) ?
C5 C6 C7 C8 . . . . 28.6(3) ?
O2 C6 C7 C11 . . . . -88.0(3) ?
C5 C6 C7 C11 . . . . 154.1(2) ?
C5 O1 C8 O3 . . . . 178.6(2) ?
C5 O1 C8 C7 . . . . -2.0(3) ?
C6 C7 C8 O3 . . . . 161.8(3) ?
C11 C7 C8 O3 . . . . 35.3(4) ?
C6 C7 C8 O1 . . . . -17.5(3) ?
C11 C7 C8 O1 . . . . -144.0(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741421
