#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/73/2227319.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227319
loop_
_publ_author_name
'Moumou, Mohamed'
'Akssira, Mohamed'
'El Ammari, Lahcen'
'Benharref, Ahmed'
'Berraho, Moha'
_publ_section_title
;
 9β-Hydroxy-1β,10α-epoxyparthenolide
;
_journal_coeditor_code           CI5157
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2395
_journal_paper_doi               10.1107/S1600536810033404
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H20 O5'
_chemical_formula_moiety         'C15 H20 O5'
_chemical_formula_sum            'C15 H20 O5'
_chemical_formula_weight         280.31
_chemical_name_common
;
9β-Hydroxy-1β,10α-epoxyparthenolide
;
_chemical_name_systematic
;
5-hydroxy-1a,4a-dimethyl-7-
methyleneperhydrodioxireno[5,6:9,10]cyclodeca[1,2-b]furan-8-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                 118.662(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2295(3)
_cell_length_b                   9.5431(3)
_cell_length_c                   9.3787(3)
_cell_measurement_reflns_used    8090
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      2.5
_cell_volume                     724.84(4)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia,1997) and PLATON (Spek, 2009)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker X8 APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω 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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8090
_diffrn_reflns_theta_full        26.70
_diffrn_reflns_theta_max         26.70
_diffrn_reflns_theta_min         2.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         1617
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0541P)²+0.0327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0903
_reflns_number_gt                1378
_reflns_number_total             1617
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5157.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2227319
_cod_database_fobs_code          2227319
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
C C1 -0.1569(3) 0.2114(3) 0.0240(3) 0.0445(5) Uani d . 1 . .
H H1 -0.0953 0.2863 0.0055 0.053 Uiso calc R 1 . .
C C2 -0.3412(3) 0.2235(3) -0.0757(3) 0.0567(7) Uani d . 1 . .
H H2A -0.3919 0.1709 -0.0227 0.068 Uiso calc R 1 . .
H H2B -0.3757 0.1811 -0.1811 0.068 Uiso calc R 1 . .
C C3 -0.4043(3) 0.3738(4) -0.1004(3) 0.0638(8) Uani d . 1 . .
H H3A -0.3743 0.4211 -0.1741 0.077 Uiso calc R 1 . .
H H3B -0.5238 0.3729 -0.1505 0.077 Uiso calc R 1 . .
C C4 -0.3354(3) 0.4546(3) 0.0564(3) 0.0522(6) Uani d . 1 . .
C C5 -0.1856(3) 0.5389(3) 0.0973(3) 0.0493(6) Uani d . 1 . .
H H5 -0.1470 0.5325 0.0167 0.059 Uiso calc R 1 . .
C C6 -0.0511(2) 0.5623(2) 0.2665(3) 0.0421(5) Uani d . 1 . .
H H6 -0.0915 0.5477 0.3448 0.051 Uiso calc R 1 . .
C C7 0.0972(3) 0.4660(2) 0.3050(3) 0.0367(5) Uani d . 1 . .
H H7 0.0907 0.4403 0.2009 0.044 Uiso calc R 1 . .
C C8 0.1049(3) 0.3287(2) 0.3942(3) 0.0423(5) Uani d . 1 . .
H H8A 0.2046 0.3294 0.4986 0.051 Uiso calc R 1 . .
H H8B 0.0116 0.3261 0.4149 0.051 Uiso calc R 1 . .
C C9 0.1036(3) 0.1953(2) 0.3041(3) 0.0395(5) Uani d . 1 . .
H H9 0.1641 0.2126 0.2439 0.047 Uiso calc R 1 . .
C C10 -0.0689(3) 0.1455(2) 0.1862(3) 0.0407(5) Uani d . 1 . .
C C11 0.2419(3) 0.5625(2) 0.3892(3) 0.0399(5) Uani d . 1 . .
C C12 0.1773(3) 0.7075(2) 0.3533(3) 0.0465(5) Uani d . 1 . .
C C13 0.3997(3) 0.5360(3) 0.4776(3) 0.0601(7) Uani d . 1 . .
H H13A 0.4749 0.6094 0.5198 0.072 Uiso calc R 1 . .
H H13B 0.4367 0.4438 0.4980 0.072 Uiso calc R 1 . .
C C14 -0.1584(3) 0.0708(3) 0.2633(3) 0.0589(7) Uani d . 1 . .
H H14A -0.1411 0.1202 0.3593 0.088 Uiso calc R 1 . .
H H14B -0.1164 -0.0229 0.2917 0.088 Uiso calc R 1 . .
H H14C -0.2744 0.0675 0.1877 0.088 Uiso calc R 1 . .
C C15 -0.3799(3) 0.4050(3) 0.1816(3) 0.0599(7) Uani d . 1 . .
H H15A -0.3367 0.4691 0.2715 0.090 Uiso calc R 1 . .
H H15B -0.3336 0.3137 0.2190 0.090 Uiso calc R 1 . .
H H15C -0.4979 0.4004 0.1347 0.090 Uiso calc R 1 . .
O O1 -0.3421(2) 0.6072(2) 0.0388(3) 0.0650(5) Uani d . 1 . .
O O2 0.1910(2) 0.09367(17) 0.4267(2) 0.0569(5) Uani d . 1 . .
H H2 0.1973 0.0204 0.3843 0.085 Uiso calc R 1 . .
O O3 0.0115(2) 0.70565(16) 0.2779(2) 0.0539(4) Uani d . 1 . .
O O4 0.2528(2) 0.81591(19) 0.3811(2) 0.0653(5) Uani d . 1 . .
O O5 -0.0845(2) 0.07350(19) 0.0434(2) 0.0549(4) Uani d . 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
O5 C1 C10 . . 59.41(15) ?
O5 C1 C2 . . 117.7(2) ?
C10 C1 C2 . . 124.9(2) ?
O5 C1 H1 . . 114.4 ?
C10 C1 H1 . . 114.4 ?
C2 C1 H1 . . 114.4 ?
C1 C2 C3 . . 113.8(2) ?
C1 C2 H2A . . 108.8 ?
C3 C2 H2A . . 108.8 ?
C1 C2 H2B . . 108.8 ?
C3 C2 H2B . . 108.8 ?
H2A C2 H2B . . 107.7 ?
C4 C3 C2 . . 112.5(2) ?
C4 C3 H3A . . 109.1 ?
C2 C3 H3A . . 109.1 ?
C4 C3 H3B . . 109.1 ?
C2 C3 H3B . . 109.1 ?
H3A C3 H3B . . 107.8 ?
O1 C4 C5 . . 58.19(16) ?
O1 C4 C15 . . 113.1(2) ?
C5 C4 C15 . . 122.8(2) ?
O1 C4 C3 . . 115.1(2) ?
C5 C4 C3 . . 115.8(2) ?
C15 C4 C3 . . 117.3(2) ?
O1 C5 C4 . . 60.23(15) ?
O1 C5 C6 . . 120.8(2) ?
C4 C5 C6 . . 123.7(2) ?
O1 C5 H5 . . 113.9 ?
C4 C5 H5 . . 113.9 ?
C6 C5 H5 . . 113.9 ?
O3 C6 C5 . . 108.32(18) ?
O3 C6 C7 . . 105.30(16) ?
C5 C6 C7 . . 110.70(18) ?
O3 C6 H6 . . 110.8 ?
C5 C6 H6 . . 110.8 ?
C7 C6 H6 . . 110.8 ?
C11 C7 C8 . . 116.15(18) ?
C11 C7 C6 . . 102.94(17) ?
C8 C7 C6 . . 116.07(17) ?
C11 C7 H7 . . 107.0 ?
C8 C7 H7 . . 107.0 ?
C6 C7 H7 . . 107.0 ?
C9 C8 C7 . . 115.12(17) ?
C9 C8 H8A . . 108.5 ?
C7 C8 H8A . . 108.5 ?
C9 C8 H8B . . 108.5 ?
C7 C8 H8B . . 108.5 ?
H8A C8 H8B . . 107.5 ?
O2 C9 C10 . . 111.51(18) ?
O2 C9 C8 . . 105.69(16) ?
C10 C9 C8 . . 113.10(17) ?
O2 C9 H9 . . 108.8 ?
C10 C9 H9 . . 108.8 ?
C8 C9 H9 . . 108.8 ?
O5 C10 C1 . . 59.26(15) ?
O5 C10 C14 . . 112.5(2) ?
C1 C10 C14 . . 122.4(2) ?
O5 C10 C9 . . 115.25(17) ?
C1 C10 C9 . . 119.00(18) ?
C14 C10 C9 . . 115.0(2) ?
C13 C11 C12 . . 121.9(2) ?
C13 C11 C7 . . 130.9(2) ?
C12 C11 C7 . . 107.19(18) ?
O4 C12 O3 . . 121.4(2) ?
O4 C12 C11 . . 128.7(2) ?
O3 C12 C11 . . 109.87(19) ?
C11 C13 H13A . . 120.0 ?
C11 C13 H13B . . 120.0 ?
H13A C13 H13B . . 120.0 ?
C10 C14 H14A . . 109.5 ?
C10 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C10 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C4 C15 H15A . . 109.5 ?
C4 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C4 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C5 O1 C4 . . 61.57(16) ?
C9 O2 H2 . . 109.5 ?
C12 O3 C6 . . 111.09(16) ?
C1 O5 C10 . . 61.33(14) ?
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
C1 O5 . 1.447(3) ?
C1 C10 . 1.477(3) ?
C1 C2 . 1.502(3) ?
C1 H1 . 0.98 ?
C2 C3 . 1.524(4) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C3 C4 . 1.505(4) ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C4 O1 . 1.463(3) ?
C4 C5 . 1.482(4) ?
C4 C15 . 1.495(4) ?
C5 O1 . 1.432(3) ?
C5 C6 . 1.490(3) ?
C5 H5 . 0.98 ?
C6 O3 . 1.469(3) ?
C6 C7 . 1.541(3) ?
C6 H6 . 0.98 ?
C7 C11 . 1.498(3) ?
C7 C8 . 1.537(3) ?
C7 H7 . 0.98 ?
C8 C9 . 1.525(3) ?
C8 H8A . 0.97 ?
C8 H8B . 0.97 ?
C9 O2 . 1.422(3) ?
C9 C10 . 1.515(3) ?
C9 H9 . 0.98 ?
C10 O5 . 1.449(3) ?
C10 C14 . 1.512(3) ?
C11 C13 . 1.310(3) ?
C11 C12 . 1.480(3) ?
C12 O4 . 1.204(3) ?
C12 O3 . 1.343(3) ?
C13 H13A . 0.93 ?
C13 H13B . 0.93 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
O2 H2 . 0.82 ?
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
_geom_hbond_publ_flag
O2 H2 O4 1_545 0.82 2.02 2.787(3) 155 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745845
