#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/61/2236121.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_2236121
loop_
_publ_author_name
'Ding, Mingruo'
'Zhang, Qiaoyin'
'Chen, Lei'
'Huang, Nianyu'
'Wang, Junzhi'
_publ_section_title
;
 (2S*,3S*,3aS*,6S*,7aR*)-3-Hydroxy-2-[(2R*,3S*)-3-isopropyloxiran-2-yl]-3,6-dimethyl-3,3a,5,6,7,7a-hexahydro-1-benzofuran-4(2H)-one
;
_journal_coeditor_code           BT6831
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2949
_journal_paper_doi               10.1107/S1600536812038470
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C15 H24 O4'
_chemical_formula_moiety         'C15 H24 O4'
_chemical_formula_sum            'C15 H24 O4'
_chemical_formula_weight         268.34
_chemical_name_systematic
;
(2S*,3S*,3aS*,6S*,7aR*)-3-Hydroxy-
2-[(2R*,3S*)-3-isopropyloxiran-2-yl]-3,6-dimethyl-
3,3a,5,6,7,7a-hexahydro-1-benzofuran-4(2H)-one
;
_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'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.616(7)
_cell_length_b                   9.261(9)
_cell_length_c                   25.12(3)
_cell_measurement_reflns_used    2058
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.73
_cell_volume                     1539(3)
_computing_cell_refinement       'CrystalClear (Rigaku, 2011)'
_computing_data_collection       'CrystalClear (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear (Rigaku, 2011)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku model name? CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1764
_diffrn_reflns_av_sigmaI/netI    0.0735
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            16467
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9797
_exptl_absorpt_correction_T_min  0.9717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2011)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0665
_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)+(0.0887P)²+0.2181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1700
_refine_ls_wR_factor_ref         0.1853
_reflns_number_gt                1568
_reflns_number_total             2058
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6831.cif
_cod_data_source_block           I
_cod_database_code               2236121
_cod_database_fobs_code          2236121
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_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_symmetry_multiplicity
C C1 0.3330(6) 0.7529(5) 0.08201(17) 0.0809(11) Uani d . 1 1
C C2 0.2584(5) 0.8871(5) 0.05651(16) 0.0771(11) Uani d . 1 1
H H2A 0.2052 0.9501 0.0840 0.093 Uiso calc R 1 1
H H2B 0.1474 0.8623 0.0330 0.093 Uiso calc R 1 1
C C3 0.4150(6) 0.9702(5) 0.02476(14) 0.0788(11) Uani d . 1 1
H H3 0.4605 0.9093 -0.0048 0.095 Uiso calc R 1 1
C C4 0.5947(6) 1.0012(5) 0.06053(14) 0.0793(11) Uani d . 1 1
H H4A 0.6926 1.0586 0.0411 0.095 Uiso calc R 1 1
H H4B 0.5500 1.0572 0.0910 0.095 Uiso calc R 1 1
C C5 0.6938(5) 0.8657(5) 0.07967(14) 0.0748(11) Uani d . 1 1
H H5 0.7693 0.8228 0.0501 0.090 Uiso calc R 1 1
C C6 0.5481(5) 0.7502(4) 0.10272(15) 0.0706(9) Uani d . 1 1
H H6 0.6049 0.6551 0.0944 0.085 Uiso calc R 1 1
C C7 0.3260(10) 1.1082(7) 0.0018(2) 0.1196(19) Uani d . 1 1
H H7A 0.2137 1.0847 -0.0208 0.179 Uiso calc R 1 1
H H7B 0.4273 1.1577 -0.0185 0.179 Uiso calc R 1 1
H H7C 0.2808 1.1692 0.0303 0.179 Uiso calc R 1 1
C C8 0.5676(5) 0.7732(3) 0.16381(14) 0.0626(8) Uani d . 1 1
C C9 0.5010(8) 0.6450(4) 0.1976(2) 0.0937(14) Uani d . 1 1
H H9A 0.5276 0.6650 0.2344 0.141 Uiso calc R 1 1
H H9B 0.5745 0.5605 0.1869 0.141 Uiso calc R 1 1
H H9C 0.3589 0.6288 0.1927 0.141 Uiso calc R 1 1
C C10 0.7945(5) 0.8060(4) 0.16665(15) 0.0658(9) Uani d . 1 1
H H10 0.8702 0.7159 0.1621 0.079 Uiso calc R 1 1
C C11 0.8628(4) 0.8785(4) 0.21676(13) 0.0581(8) Uani d . 1 1
H H11 0.7903 0.9670 0.2264 0.070 Uiso calc R 1 1
C C12 0.9471(5) 0.7963(4) 0.26096(14) 0.0634(8) Uani d . 1 1
H H12 0.9520 0.6916 0.2554 0.076 Uiso calc R 1 1
C C13 0.9347(5) 0.8420(4) 0.31751(14) 0.0690(9) Uani d . 1 1
H H13 0.9259 0.9477 0.3180 0.083 Uiso calc R 1 1
C C14 0.7449(8) 0.7838(6) 0.3432(2) 0.1076(17) Uani d . 1 1
H H14A 0.6293 0.8128 0.3227 0.161 Uiso calc R 1 1
H H14B 0.7335 0.8212 0.3787 0.161 Uiso calc R 1 1
H H14C 0.7514 0.6803 0.3445 0.161 Uiso calc R 1 1
C C15 1.1278(9) 0.7993(8) 0.3472(2) 0.1161(19) Uani d . 1 1
H H15A 1.1347 0.6961 0.3501 0.174 Uiso calc R 1 1
H H15B 1.1262 0.8411 0.3822 0.174 Uiso calc R 1 1
H H15C 1.2434 0.8341 0.3280 0.174 Uiso calc R 1 1
O O1 0.2253(6) 0.6483(5) 0.08748(18) 0.1301(15) Uani d . 1 1
O O2 0.8347(3) 0.8990(3) 0.12242(9) 0.0749(7) Uani d . 1 1
O O3 0.4646(3) 0.9014(2) 0.17901(9) 0.0613(6) Uani d . 1 1
H H3A 0.3551 0.8803 0.1922 0.092 Uiso calc R 1 1
O O4 1.0785(3) 0.8795(4) 0.22651(11) 0.0802(8) Uani d . 1 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
O1 C1 C2 121.6(4)
O1 C1 C6 120.0(5)
C2 C1 C6 118.4(4)
C1 C2 C3 115.2(4)
C1 C2 H2A 108.5
C3 C2 H2A 108.5
C1 C2 H2B 108.5
C3 C2 H2B 108.5
H2A C2 H2B 107.5
C4 C3 C7 111.7(4)
C4 C3 C2 108.6(3)
C7 C3 C2 111.2(4)
C4 C3 H3 108.4
C7 C3 H3 108.4
C2 C3 H3 108.4
C5 C4 C3 112.1(4)
C5 C4 H4A 109.2
C3 C4 H4A 109.2
C5 C4 H4B 109.2
C3 C4 H4B 109.2
H4A C4 H4B 107.9
O2 C5 C4 109.9(3)
O2 C5 C6 105.6(3)
C4 C5 C6 115.2(3)
O2 C5 H5 108.7
C4 C5 H5 108.7
C6 C5 H5 108.7
C1 C6 C5 116.3(4)
C1 C6 C8 114.5(3)
C5 C6 C8 102.8(3)
C1 C6 H6 107.6
C5 C6 H6 107.6
C8 C6 H6 107.6
C3 C7 H7A 109.5
C3 C7 H7B 109.5
H7A C7 H7B 109.5
C3 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O3 C8 C9 111.2(3)
O3 C8 C10 107.0(3)
C9 C8 C10 114.3(3)
O3 C8 C6 109.9(3)
C9 C8 C6 114.7(3)
C10 C8 C6 98.9(3)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O2 C10 C11 109.1(3)
O2 C10 C8 105.4(3)
C11 C10 C8 115.1(3)
O2 C10 H10 109.1
C11 C10 H10 109.1
C8 C10 H10 109.1
O4 C11 C12 59.8(2)
O4 C11 C10 116.3(3)
C12 C11 C10 121.5(3)
O4 C11 H11 115.8
C12 C11 H11 115.8
C10 C11 H11 115.8
O4 C12 C11 59.8(2)
O4 C12 C13 116.9(3)
C11 C12 C13 124.0(3)
O4 C12 H12 114.9
C11 C12 H12 114.9
C13 C12 H12 114.9
C12 C13 C14 110.6(4)
C12 C13 C15 110.3(3)
C14 C13 C15 113.1(4)
C12 C13 H13 107.5
C14 C13 H13 107.5
C15 C13 H13 107.5
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C13 C15 H15A 109.5
C13 C15 H15B 109.5
H15A C15 H15B 109.5
C13 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C10 O2 C5 109.0(3)
C8 O3 H3A 109.5
C11 O4 C12 60.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.210(6)
C1 C2 1.482(7)
C1 C6 1.515(6)
C2 C3 1.517(6)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.518(5)
C3 C7 1.520(8)
C3 H3 0.9800
C4 C5 1.495(7)
C4 H4A 0.9700
C4 H4B 0.9700
C5 O2 1.455(4)
C5 C6 1.552(6)
C5 H5 0.9800
C6 C8 1.554(5)
C6 H6 0.9800
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 O3 1.420(4)
C8 C9 1.525(5)
C8 C10 1.533(5)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 O2 1.431(4)
C10 C11 1.497(5)
C10 H10 0.9800
C11 O4 1.448(4)
C11 C12 1.457(5)
C11 H11 0.9800
C12 O4 1.448(4)
C12 C13 1.484(5)
C12 H12 0.9800
C13 C14 1.512(6)
C13 C15 1.531(6)
C13 H13 0.9800
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
O3 H3A 0.8200
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 H3A O4 1_455 0.82 2.02 2.827(4) 166.4
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
O1 C1 C2 C3 -146.8(5)
C6 C1 C2 C3 34.8(5)
C1 C2 C3 C4 -54.8(5)
C1 C2 C3 C7 -178.1(4)
C7 C3 C4 C5 -175.3(4)
C2 C3 C4 C5 61.8(4)
C3 C4 C5 O2 -167.6(3)
C3 C4 C5 C6 -48.5(4)
O1 C1 C6 C5 161.9(4)
C2 C1 C6 C5 -19.6(5)
O1 C1 C6 C8 -78.2(6)
C2 C1 C6 C8 100.2(4)
O2 C5 C6 C1 148.0(3)
C4 C5 C6 C1 26.6(5)
O2 C5 C6 C8 22.0(4)
C4 C5 C6 C8 -99.4(3)
C1 C6 C8 O3 -53.2(4)
C5 C6 C8 O3 74.0(3)
C1 C6 C8 C9 73.1(5)
C5 C6 C8 C9 -159.8(3)
C1 C6 C8 C10 -164.9(3)
C5 C6 C8 C10 -37.8(3)
O3 C8 C10 O2 -72.2(4)
C9 C8 C10 O2 164.2(3)
C6 C8 C10 O2 41.9(3)
O3 C8 C10 C11 48.0(4)
C9 C8 C10 C11 -75.6(4)
C6 C8 C10 C11 162.1(3)
O2 C10 C11 O4 -76.3(4)
C8 C10 C11 O4 165.6(3)
O2 C10 C11 C12 -145.5(3)
C8 C10 C11 C12 96.4(4)
C10 C11 C12 O4 104.2(3)
O4 C11 C12 C13 103.9(4)
C10 C11 C12 C13 -152.0(3)
O4 C12 C13 C14 160.0(3)
C11 C12 C13 C14 89.8(4)
O4 C12 C13 C15 -74.1(4)
C11 C12 C13 C15 -144.3(4)
C11 C10 O2 C5 -154.0(3)
C8 C10 O2 C5 -29.9(4)
C4 C5 O2 C10 129.2(3)
C6 C5 O2 C10 4.4(4)
C10 C11 O4 C12 -112.7(4)
C13 C12 O4 C11 -115.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658034
