#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/40/2224010.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_2224010
loop_
_publ_author_name
'Cheng, Jing-Li'
'Zhou, Yong'
'Lin, Fu-Cheng'
'Zhao, Jin-Hao'
'Zhu, Guo-Nian'
_publ_section_title
;
 Trichodermol (4α-hydroxy-12,13-epoxytrichothec-9-ene)
;
_journal_coeditor_code           SI2217
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2879
_journal_paper_doi               10.1107/S1600536809044080
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H22 O3'
_chemical_formula_moiety         'C15 H22 O3'
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.34
_chemical_name_common
;
Trichodermol
;
_chemical_name_systematic
;
4α-hydroxy-12,13-epoxytrichothec-9-ene
;
_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'
_cell_angle_alpha                90.0000
_cell_angle_beta                 96.7507(11)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   6.8284(2)
_cell_length_b                   6.6209(3)
_cell_length_c                   14.7170(6)
_cell_measurement_reflns_used    6124
_cell_measurement_temperature    296.0(10)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.0
_cell_volume                     660.74(4)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'CRYSTALS (Watkin et al.,  1996)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      296.0(10)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6503
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.44
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             272.00
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.15
_refine_ls_extinction_coef       18E1(3)
_refine_ls_extinction_method     'Larson (1970), equation 22'
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1634
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[0.0012Fo² + 1.5σ(Fo²)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0946
_reflns_number_gt                1540
_reflns_number_total             1634
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            si2217.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2224010
_cod_database_fobs_code          2224010
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-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 0.84609(16) 0.3577(2) 0.83213(8) 0.0329(3) Uani d . 1.00 . .
O O2 0.9112(2) 0.9341(2) 0.83678(11) 0.0535(4) Uani d . 1.00 . .
O O3 0.44991(17) 0.5728(2) 0.95141(8) 0.0428(3) Uani d . 1.00 . .
C C1 0.8680(2) 0.4910(2) 0.75578(11) 0.0295(4) Uani d . 1.00 . .
C C2 0.9296(2) 0.3595(3) 0.68075(12) 0.0389(4) Uani d . 1.00 . .
C C3 0.8120(2) 0.3061(3) 0.60656(12) 0.0423(5) Uani d . 1.00 . .
C C4 0.5978(2) 0.3670(3) 0.59348(12) 0.0484(5) Uani d . 1.00 . .
C C5 0.5275(2) 0.4606(3) 0.67912(12) 0.0394(4) Uani d . 1.00 . .
C C6 0.6784(2) 0.6115(2) 0.72646(11) 0.0307(4) Uani d . 1.00 . .
C C7 0.6045(2) 0.7082(2) 0.81427(11) 0.0298(4) Uani d . 1.00 . .
C C8 0.7735(2) 0.8181(2) 0.87935(12) 0.0374(4) Uani d . 1.00 . .
C C9 0.8824(2) 0.6492(3) 0.93698(12) 0.0398(4) Uani d . 1.00 . .
C C10 0.7723(2) 0.4555(3) 0.90883(11) 0.0326(4) Uani d . 1.00 . .
C C11 0.5685(2) 0.5348(2) 0.87747(11) 0.0294(4) Uani d . 1.00 . .
C C12 0.3896(2) 0.4194(3) 0.88380(12) 0.0418(5) Uani d . 1.00 . .
C C13 0.8819(4) 0.1859(4) 0.52998(14) 0.0596(6) Uani d . 1.00 . .
C C14 0.7229(3) 0.7762(3) 0.65783(14) 0.0505(5) Uani d . 1.00 . .
C C15 0.4273(2) 0.8481(3) 0.79217(14) 0.0485(5) Uani d . 1.00 . .
H H1 0.9748 0.5866 0.7745 0.035 Uiso c R 1.00 . .
H H2 1.0589 0.3125 0.6868 0.047 Uiso c R 1.00 . .
H H8 0.7109 0.9068 0.9207 0.045 Uiso c R 1.00 . .
H H10 0.7711 0.3629 0.9607 0.039 Uiso c R 1.00 . .
H H41 0.5787 0.4649 0.5442 0.058 Uiso c R 1.00 . .
H H42 0.5188 0.2479 0.5769 0.058 Uiso c R 1.00 . .
H H51 0.4041 0.5308 0.6617 0.047 Uiso c R 1.00 . .
H H52 0.5066 0.3534 0.7219 0.047 Uiso c R 1.00 . .
H H91 1.0183 0.6401 0.9241 0.048 Uiso c R 1.00 . .
H H92 0.8794 0.6749 1.0017 0.048 Uiso c R 1.00 . .
H H121 0.3980 0.2778 0.9006 0.050 Uiso c R 1.00 . .
H H122 0.2745 0.4411 0.8396 0.050 Uiso c R 1.00 . .
H H131 0.8038 0.0656 0.5201 0.072 Uiso c R 1.00 . .
H H132 1.0178 0.1497 0.5458 0.072 Uiso c R 1.00 . .
H H133 0.8688 0.2656 0.4751 0.072 Uiso c R 1.00 . .
H H141 0.7607 0.7139 0.6036 0.061 Uiso c R 1.00 . .
H H142 0.8285 0.8602 0.6850 0.061 Uiso c R 1.00 . .
H H143 0.6072 0.8572 0.6421 0.061 Uiso c R 1.00 . .
H H151 0.3317 0.7839 0.7485 0.058 Uiso c R 1.00 . .
H H152 0.4697 0.9723 0.7670 0.058 Uiso c R 1.00 . .
H H153 0.3691 0.8760 0.8471 0.058 Uiso c R 1.00 . .
H H201 0.8723 1.0539 0.8294 0.066 Uiso c R 1.00 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, 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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C10 . . . 114.24(13) ?
C11 O3 C12 . . . 60.14(11) ?
O1 C1 C2 . . . 106.26(14) ?
O1 C1 C6 . . . 111.87(12) ?
C2 C1 C6 . . . 113.14(12) ?
C1 C2 C3 . . . 124.36(16) ?
C2 C3 C4 . . . 121.26(18) ?
C2 C3 C13 . . . 122.95(18) ?
C4 C3 C13 . . . 115.78(17) ?
C3 C4 C5 . . . 113.36(15) ?
C4 C5 C6 . . . 112.11(15) ?
C1 C6 C5 . . . 106.63(14) ?
C1 C6 C7 . . . 108.69(12) ?
C1 C6 C14 . . . 109.07(15) ?
C5 C6 C7 . . . 111.85(13) ?
C5 C6 C14 . . . 109.60(14) ?
C7 C6 C14 . . . 110.88(15) ?
C6 C7 C8 . . . 113.63(13) ?
C6 C7 C11 . . . 106.61(14) ?
C6 C7 C15 . . . 113.16(13) ?
C8 C7 C11 . . . 97.80(12) ?
C8 C7 C15 . . . 110.62(15) ?
C11 C7 C15 . . . 114.07(14) ?
O2 C8 C7 . . . 117.07(15) ?
O2 C8 C9 . . . 109.54(14) ?
C7 C8 C9 . . . 105.64(15) ?
C8 C9 C10 . . . 105.72(13) ?
O1 C10 C9 . . . 112.64(14) ?
O1 C10 C11 . . . 108.15(12) ?
C9 C10 C11 . . . 101.46(15) ?
O3 C11 C7 . . . 118.26(15) ?
O3 C11 C10 . . . 113.99(12) ?
O3 C11 C12 . . . 59.75(11) ?
C7 C11 C10 . . . 103.95(13) ?
C7 C11 C12 . . . 129.49(14) ?
C10 C11 C12 . . . 123.35(16) ?
O3 C12 C11 . . . 60.11(11) ?
C8 O2 H201 . . . 110.7 ?
O1 C1 H1 . . . 108.5 ?
C2 C1 H1 . . . 108.5 ?
C6 C1 H1 . . . 108.5 ?
C1 C2 H2 . . . 117.8 ?
C3 C2 H2 . . . 117.8 ?
C3 C4 H41 . . . 108.5 ?
C3 C4 H42 . . . 108.5 ?
C5 C4 H41 . . . 108.5 ?
C5 C4 H42 . . . 108.5 ?
H41 C4 H42 . . . 109.5 ?
C4 C5 H51 . . . 108.8 ?
C4 C5 H52 . . . 108.8 ?
C6 C5 H51 . . . 108.8 ?
C6 C5 H52 . . . 108.8 ?
H51 C5 H52 . . . 109.5 ?
O2 C8 H8 . . . 108.1 ?
C7 C8 H8 . . . 108.1 ?
C9 C8 H8 . . . 108.1 ?
C8 C9 H91 . . . 110.4 ?
C8 C9 H92 . . . 110.4 ?
C10 C9 H91 . . . 110.4 ?
C10 C9 H92 . . . 110.4 ?
H91 C9 H92 . . . 109.5 ?
O1 C10 H10 . . . 111.4 ?
C9 C10 H10 . . . 111.4 ?
C11 C10 H10 . . . 111.4 ?
O3 C12 H121 . . . 120.0 ?
O3 C12 H122 . . . 120.0 ?
C11 C12 H121 . . . 120.0 ?
C11 C12 H122 . . . 120.0 ?
H121 C12 H122 . . . 109.5 ?
C3 C13 H131 . . . 109.5 ?
C3 C13 H132 . . . 109.5 ?
C3 C13 H133 . . . 109.5 ?
H131 C13 H132 . . . 109.5 ?
H131 C13 H133 . . . 109.5 ?
H132 C13 H133 . . . 109.5 ?
C6 C14 H141 . . . 109.5 ?
C6 C14 H142 . . . 109.5 ?
C6 C14 H143 . . . 109.5 ?
H141 C14 H142 . . . 109.5 ?
H141 C14 H143 . . . 109.5 ?
H142 C14 H143 . . . 109.5 ?
C7 C15 H151 . . . 109.5 ?
C7 C15 H152 . . . 109.5 ?
C7 C15 H153 . . . 109.5 ?
H151 C15 H152 . . . 109.5 ?
H151 C15 H153 . . . 109.5 ?
H152 C15 H153 . . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . . 1.450(2) ?
O1 C10 . . 1.443(2) ?
O2 C8 . . 1.416(2) ?
O3 C11 . . 1.453(2) ?
O3 C12 . . 1.447(2) ?
C1 C2 . . 1.504(2) ?
C1 C6 . . 1.539(2) ?
C2 C3 . . 1.325(2) ?
C3 C4 . . 1.508(2) ?
C3 C13 . . 1.503(3) ?
C4 C5 . . 1.531(2) ?
C5 C6 . . 1.542(2) ?
C6 C7 . . 1.577(2) ?
C6 C14 . . 1.541(2) ?
C7 C8 . . 1.587(2) ?
C7 C11 . . 1.516(2) ?
C7 C15 . . 1.528(2) ?
C8 C9 . . 1.541(2) ?
C9 C10 . . 1.520(2) ?
C10 C11 . . 1.508(2) ?
C11 C12 . . 1.453(2) ?
O2 H201 . . 0.840 ?
C1 H1 . . 0.980 ?
C2 H2 . . 0.930 ?
C4 H41 . . 0.970 ?
C4 H42 . . 0.970 ?
C5 H51 . . 0.970 ?
C5 H52 . . 0.970 ?
C8 H8 . . 0.980 ?
C9 H91 . . 0.970 ?
C9 H92 . . 0.970 ?
C10 H10 . . 0.980 ?
C12 H121 . . 0.970 ?
C12 H122 . . 0.970 ?
C13 H131 . . 0.960 ?
C13 H132 . . 0.960 ?
C13 H133 . . 0.960 ?
C14 H141 . . 0.960 ?
C14 H142 . . 0.960 ?
C14 H143 . . 0.960 ?
C15 H151 . . 0.960 ?
C15 H152 . . 0.960 ?
C15 H153 . . 0.960 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H201 O1 . . 1_565 0.840 2.020 2.839(2) 164.9 yes
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 O1 C10 C9 . . . . -48.89(16) ?
C1 O1 C10 C11 . . . . 62.42(17) ?
C10 O1 C1 C2 . . . . -175.48(11) ?
C10 O1 C1 C6 . . . . -51.55(16) ?
C12 O3 C11 C7 . . . . 121.49(16) ?
C12 O3 C11 C10 . . . . -115.92(18) ?
O1 C1 C2 C3 . . . . 105.4(2) ?
O1 C1 C6 C5 . . . . -71.96(16) ?
O1 C1 C6 C7 . . . . 48.78(17) ?
O1 C1 C6 C14 . . . . 169.78(14) ?
C2 C1 C6 C5 . . . . 48.01(18) ?
C2 C1 C6 C7 . . . . 168.75(14) ?
C2 C1 C6 C14 . . . . -70.25(19) ?
C6 C1 C2 C3 . . . . -17.7(2) ?
C1 C2 C3 C4 . . . . -3.0(3) ?
C1 C2 C3 C13 . . . . 175.8(2) ?
C2 C3 C4 C5 . . . . -9.8(3) ?
C13 C3 C4 C5 . . . . 171.3(2) ?
C3 C4 C5 C6 . . . . 43.1(2) ?
C4 C5 C6 C1 . . . . -61.64(19) ?
C4 C5 C6 C7 . . . . 179.67(15) ?
C4 C5 C6 C14 . . . . 56.3(2) ?
C1 C6 C7 C8 . . . . 47.34(19) ?
C1 C6 C7 C11 . . . . -59.22(16) ?
C1 C6 C7 C15 . . . . 174.58(15) ?
C5 C6 C7 C8 . . . . 164.80(14) ?
C5 C6 C7 C11 . . . . 58.24(16) ?
C5 C6 C7 C15 . . . . -68.0(2) ?
C14 C6 C7 C8 . . . . -72.54(18) ?
C14 C6 C7 C11 . . . . -179.10(14) ?
C14 C6 C7 C15 . . . . 54.7(2) ?
C6 C7 C8 O2 . . . . 40.8(2) ?
C6 C7 C8 C9 . . . . -81.40(17) ?
C6 C7 C11 O3 . . . . -163.39(12) ?
C6 C7 C11 C10 . . . . 69.08(15) ?
C6 C7 C11 C12 . . . . -90.7(2) ?
C8 C7 C11 O3 . . . . 79.03(15) ?
C8 C7 C11 C10 . . . . -48.50(15) ?
C8 C7 C11 C12 . . . . 151.67(18) ?
C11 C7 C8 O2 . . . . 152.82(15) ?
C11 C7 C8 C9 . . . . 30.61(16) ?
C15 C7 C8 O2 . . . . -87.74(19) ?
C15 C7 C8 C9 . . . . 150.05(15) ?
C15 C7 C11 O3 . . . . -37.8(2) ?
C15 C7 C11 C10 . . . . -165.28(15) ?
C15 C7 C11 C12 . . . . 34.9(2) ?
O2 C8 C9 C10 . . . . -129.73(15) ?
C7 C8 C9 C10 . . . . -2.80(18) ?
C8 C9 C10 O1 . . . . 88.78(16) ?
C8 C9 C10 C11 . . . . -26.62(17) ?
O1 C10 C11 O3 . . . . 159.65(14) ?
O1 C10 C11 C7 . . . . -70.22(17) ?
O1 C10 C11 C12 . . . . 91.20(19) ?
C9 C10 C11 O3 . . . . -81.67(17) ?
C9 C10 C11 C7 . . . . 48.45(16) ?
C9 C10 C11 C12 . . . . -150.13(16) ?
C7 C11 C12 O3 . . . . -103.3(2) ?
C10 C11 C12 O3 . . . . 100.35(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743672
