#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/57/2215753.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_2215753
loop_
_publ_author_name
'Wang, Wen-liang'
'Tao, Hong-wen'
'Sun, Wei'
'Gu, Qian-Qun'
'Zhu, Wei-Ming'
_publ_section_title
(3aS,5aR,6R,8aR)-3a-Hydroxy-5a-methyl-6-[(1R,2E,4R)-1,4,5-trimethyl-2-hexen-1-yl]-3a,4,5,5a,6,7,8,8a-octahydro-2H-cyclopenta[e]benzofuran-2-one
_journal_coeditor_code           AV3110
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4196
_journal_page_last               o4196
_journal_paper_doi               10.1107/S1600536807047307
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C21 H32 O3'
_chemical_formula_moiety         'C21 H32 O3'
_chemical_formula_sum            'C21 H32 O3'
_chemical_formula_weight         332.47
_chemical_name_common            'Demethylincisterol A3'
_chemical_name_systematic
;
(3aS,5aR,6R,8aR)-3a-Hydroxy-5a-methyl-6-[(1R,2E,4R)-1,4,5-trimethyl-2-hexen-
1-yl]-3a,4,5,5a,6,7,8,8a-octahydro-2H-cyclopenta[e]benzofuran-2-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
_cell_angle_alpha                90.00
_cell_angle_beta                 95.639(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.0506(9)
_cell_length_b                   6.7640(8)
_cell_length_c                   18.858(2)
_cell_measurement_reflns_used    2840
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.133
_cell_measurement_theta_min      2.336
_cell_volume                     1021.9(2)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5311
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.080
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flake
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.145
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876--881.'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         1965
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0454
_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)+(0.0482P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1127
_reflns_number_gt                1247
_reflns_number_total             1965
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            av3110.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (21 time).

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

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (21 time).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21
_cod_database_code               2215753
_cod_database_fobs_code          2215753
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
O O1 1.4534(3) 0.2461(4) 0.46674(13) 0.0650(8) Uani d . 1
O O2 1.4101(3) 0.2856(5) 0.58115(15) 0.0768(9) Uani d . 1
O O3 1.4982(3) 0.4173(5) 0.36379(13) 0.0699(8) Uani d . 1
H H3 1.5217 0.5222 0.3842 0.105 Uiso calc R 1
C C1 1.3731(4) 0.3295(6) 0.5192(2) 0.0601(10) Uani d . 1
C C2 1.2432(4) 0.4584(6) 0.48848(19) 0.0558(10) Uani d . 1
H H2 1.1721 0.5330 0.5138 0.067 Uiso calc R 1
C C3 1.2414(4) 0.4536(5) 0.41862(18) 0.0471(9) Uani d . 1
C C4 1.3778(4) 0.3200(6) 0.39805(19) 0.0526(10) Uani d . 1
C C5 1.3090(4) 0.1516(6) 0.3518(2) 0.0615(11) Uani d . 1
H H5A 1.2516 0.0595 0.3804 0.074 Uiso calc R 1
H H5B 1.4002 0.0816 0.3330 0.074 Uiso calc R 1
C C6 1.1873(4) 0.2264(6) 0.28980(18) 0.0576(10) Uani d . 1
H H6A 1.2492 0.3018 0.2574 0.069 Uiso calc R 1
H H6B 1.1380 0.1137 0.2638 0.069 Uiso calc R 1
C C7 1.0479(4) 0.3558(5) 0.31402(17) 0.0447(8) Uani d . 1
C C8 1.1314(4) 0.5317(5) 0.35810(18) 0.0462(9) Uani d . 1
H H8 1.2034 0.5999 0.3270 0.055 Uiso calc R 1
C C9 0.9890(4) 0.6699(6) 0.36851(19) 0.0589(10) Uani d . 1
H H9A 1.0285 0.8045 0.3760 0.071 Uiso calc R 1
H H9B 0.9309 0.6295 0.4088 0.071 Uiso calc R 1
C C10 0.8755(4) 0.6518(6) 0.29844(19) 0.0601(10) Uani d . 1
H H10A 0.8795 0.7724 0.2709 0.072 Uiso calc R 1
H H10B 0.7610 0.6289 0.3082 0.072 Uiso calc R 1
C C11 0.9407(4) 0.4739(5) 0.25643(17) 0.0515(9) Uani d . 1
H H11 1.0169 0.5279 0.2239 0.062 Uiso calc R 1
C C12 0.7992(4) 0.3695(6) 0.21038(19) 0.0614(11) Uani d . 1
H H12 0.7251 0.3099 0.2427 0.074 Uiso calc R 1
C C13 0.6990(5) 0.5150(7) 0.16491(19) 0.0665(11) Uani d . 1
H H13 0.7526 0.5764 0.1294 0.080 Uiso calc R 1
C C14 0.5453(5) 0.5652(7) 0.1695(2) 0.0693(12) Uani d . 1
H H14 0.4914 0.4964 0.2033 0.083 Uiso calc R 1
C C15 0.4421(5) 0.7175(7) 0.1283(2) 0.0797(14) Uani d . 1
H H15 0.5070 0.7697 0.0912 0.096 Uiso calc R 1
C C16 0.2811(6) 0.6235(10) 0.0917(3) 0.1076(19) Uani d . 1
H H16 0.2198 0.5626 0.1285 0.129 Uiso calc R 1
C C17 0.1679(7) 0.7832(14) 0.0527(3) 0.172(3) Uani d . 1
H H17A 0.2280 0.8488 0.0180 0.258 Uiso calc R 1
H H17B 0.1358 0.8781 0.0867 0.258 Uiso calc R 1
H H17C 0.0699 0.7216 0.0293 0.258 Uiso calc R 1
C C18 0.9365(4) 0.2377(6) 0.35926(19) 0.0560(10) Uani d . 1
H H18A 0.9008 0.1185 0.3346 0.084 Uiso calc R 1
H H18B 0.8406 0.3154 0.3677 0.084 Uiso calc R 1
H H18C 0.9977 0.2047 0.4039 0.084 Uiso calc R 1
C C19 0.8610(6) 0.2045(7) 0.1650(2) 0.0952(16) Uani d . 1
H H19A 0.7688 0.1507 0.1350 0.143 Uiso calc R 1
H H19B 0.9110 0.1024 0.1953 0.143 Uiso calc R 1
H H19C 0.9424 0.2563 0.1359 0.143 Uiso calc R 1
C C20 0.4074(8) 0.8880(10) 0.1784(3) 0.145(3) Uani d . 1
H H20A 0.3362 0.8424 0.2130 0.217 Uiso calc R 1
H H20B 0.3535 0.9941 0.1512 0.217 Uiso calc R 1
H H20C 0.5108 0.9343 0.2024 0.217 Uiso calc R 1
C C21 0.3219(7) 0.4647(13) 0.0398(3) 0.155(3) Uani d . 1
H H21A 0.3817 0.5221 0.0033 0.233 Uiso calc R 1
H H21B 0.2204 0.4061 0.0185 0.233 Uiso calc R 1
H H21C 0.3896 0.3649 0.0646 0.233 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
_geom_angle_publ_flag
C1 O1 C4 108.5(3) y
C4 O3 H3 109.5 y
O2 C1 O1 120.7(4) y
O2 C1 C2 129.5(4) ?
O1 C1 C2 109.7(3) ?
C3 C2 C1 108.9(3) ?
C3 C2 H2 125.5 ?
C1 C2 H2 125.5 ?
C2 C3 C8 135.5(3) y
C2 C3 C4 109.7(3) y
C8 C3 C4 114.5(3) ?
O3 C4 O1 109.0(3) y
O3 C4 C3 113.4(3) ?
O1 C4 C3 103.2(3) y
O3 C4 C5 108.9(3) ?
O1 C4 C5 110.6(3) y
C3 C4 C5 111.6(3) ?
C4 C5 C6 111.2(3) ?
C4 C5 H5A 109.4 ?
C6 C5 H5A 109.4 ?
C4 C5 H5B 109.4 ?
C6 C5 H5B 109.4 ?
H5A C5 H5B 108.0 ?
C7 C6 C5 113.2(3) ?
C7 C6 H6A 108.9 ?
C5 C6 H6A 108.9 ?
C7 C6 H6B 108.9 ?
C5 C6 H6B 108.9 ?
H6A C6 H6B 107.8 ?
C18 C7 C6 110.9(3) y
C18 C7 C11 110.2(3) y
C6 C7 C11 117.6(3) y
C18 C7 C8 110.3(3) y
C6 C7 C8 107.7(2) y
C11 C7 C8 99.3(3) y
C3 C8 C9 121.9(3) y
C3 C8 C7 109.5(3) y
C9 C8 C7 104.4(2) y
C3 C8 H8 106.7 ?
C9 C8 H8 106.7 ?
C7 C8 H8 106.7 ?
C8 C9 C10 103.6(3) ?
C8 C9 H9A 111.0 ?
C10 C9 H9A 111.0 ?
C8 C9 H9B 111.0 ?
C10 C9 H9B 111.0 ?
H9A C9 H9B 109.0 ?
C9 C10 C11 107.3(3) ?
C9 C10 H10A 110.3 ?
C11 C10 H10A 110.3 ?
C9 C10 H10B 110.3 ?
C11 C10 H10B 110.3 ?
H10A C10 H10B 108.5 ?
C12 C11 C7 119.6(3) ?
C12 C11 C10 112.0(3) ?
C7 C11 C10 103.6(3) ?
C12 C11 H11 107.0 ?
C7 C11 H11 107.0 ?
C10 C11 H11 107.0 ?
C13 C12 C19 110.5(3) ?
C13 C12 C11 110.6(3) ?
C19 C12 C11 113.0(3) ?
C13 C12 H12 107.5 ?
C19 C12 H12 107.5 ?
C11 C12 H12 107.5 ?
C14 C13 C12 127.0(4) y
C14 C13 H13 116.5 y
C12 C13 H13 116.5 y
C13 C14 C15 129.3(4) y
C13 C14 H14 115.4 ?
C15 C14 H14 115.4 ?
C14 C15 C20 108.9(3) ?
C14 C15 C16 110.4(4) ?
C20 C15 C16 112.9(4) ?
C14 C15 H15 108.2 ?
C20 C15 H15 108.2 ?
C16 C15 H15 108.2 ?
C21 C16 C15 110.8(4) ?
C21 C16 C17 110.1(5) ?
C15 C16 C17 110.7(6) ?
C21 C16 H16 108.4 ?
C15 C16 H16 108.4 ?
C17 C16 H16 108.4 ?
C16 C17 H17A 109.5 ?
C16 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C16 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
C7 C18 H18A 109.5 ?
C7 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C7 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C12 C19 H19A 109.5 ?
C12 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C12 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C15 C20 H20A 109.5 ?
C15 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C15 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
C16 C21 H21A 109.5 ?
C16 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C16 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.357(4) y
O1 C4 1.464(4) y
O2 C1 1.213(4) y
O3 C4 1.383(4) y
O3 H3 0.8200 y
C1 C2 1.439(5) ?
C2 C3 1.317(4) ?
C2 H2 0.9300 ?
C3 C8 1.472(4) ?
C3 C4 1.503(5) ?
C4 C5 1.507(5) ?
C5 C6 1.536(5) ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
C6 C7 1.528(4) ?
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C7 C18 1.524(5) ?
C7 C11 1.542(5) ?
C7 C8 1.565(5) ?
C8 C9 1.507(5) ?
C8 H8 0.9800 ?
C9 C10 1.536(4) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 C11 1.560(5) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 C12 1.535(5) ?
C11 H11 0.9800 ?
C12 C13 1.490(5) ?
C12 C19 1.520(5) ?
C12 H12 0.9800 ?
C13 C14 1.294(5) y
C13 H13 0.9300 ?
C14 C15 1.493(6) ?
C14 H14 0.9300 ?
C15 C20 1.534(7) ?
C15 C16 1.544(7) ?
C15 H15 0.9800 ?
C16 C21 1.512(8) ?
C16 C17 1.551(9) ?
C16 H16 0.9800 ?
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 0.9600 ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 0.9600 ?
C20 H20A 0.9600 ?
C20 H20B 0.9600 ?
C20 H20C 0.9600 ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 0.9600 ?
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 2_856 0.82 1.96 2.771(4) 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
C4 O1 C1 O2 177.5(3)
C4 O1 C1 C2 0.3(4)
O2 C1 C2 C3 -176.2(4)
O1 C1 C2 C3 0.7(4)
C1 C2 C3 C8 172.0(4)
C1 C2 C3 C4 -1.4(4)
C1 O1 C4 O3 119.8(3)
C1 O1 C4 C3 -1.1(4)
C1 O1 C4 C5 -120.5(3)
C2 C3 C4 O3 -116.3(4)
C8 C3 C4 O3 68.8(4)
C2 C3 C4 O1 1.5(4)
C8 C3 C4 O1 -173.4(3)
C2 C3 C4 C5 120.3(3)
C8 C3 C4 C5 -54.7(4)
O3 C4 C5 C6 -76.4(4)
O1 C4 C5 C6 163.7(3)
C3 C4 C5 C6 49.5(4)
C4 C5 C6 C7 -53.5(4)
C5 C6 C7 C18 -64.2(4)
C5 C6 C7 C11 167.6(3)
C5 C6 C7 C8 56.6(4)
C2 C3 C8 C9 7.5(6)
C4 C3 C8 C9 -179.3(3)
C2 C3 C8 C7 -114.6(5)
C4 C3 C8 C7 58.7(4)
C18 C7 C8 C3 63.4(3)
C6 C7 C8 C3 -57.8(3)
C11 C7 C8 C3 179.2(2)
C18 C7 C8 C9 -68.6(3)
C6 C7 C8 C9 170.2(3)
C11 C7 C8 C9 47.1(3)
C3 C8 C9 C10 -160.2(3)
C7 C8 C9 C10 -35.8(4)
C8 C9 C10 C11 10.5(4)
C18 C7 C11 C12 -48.5(4)
C6 C7 C11 C12 79.9(4)
C8 C7 C11 C12 -164.4(3)
C18 C7 C11 C10 76.9(3)
C6 C7 C11 C10 -154.6(3)
C8 C7 C11 C10 -38.9(3)
C9 C10 C11 C12 148.9(3)
C9 C10 C11 C7 18.7(4)
C7 C11 C12 C13 172.9(3)
C10 C11 C12 C13 51.6(4)
C7 C11 C12 C19 -62.7(4)
C10 C11 C12 C19 176.0(3)
C19 C12 C13 C14 121.2(5)
C11 C12 C13 C14 -112.9(5)
C12 C13 C14 C15 176.2(4)
C13 C14 C15 C20 -111.3(6)
C13 C14 C15 C16 124.2(5)
C14 C15 C16 C21 -61.1(6)
C20 C15 C16 C21 176.7(5)
C14 C15 C16 C17 176.5(4)
C20 C15 C16 C17 54.3(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10365731
2 PubChem 15215298
