#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/83/2228309.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_2228309
loop_
_publ_author_name
'Moumou, Mohamed'
'Akssira, Mohamed'
'El Hakmaoui, Ahmed'
'Elammari, Lahcen'
'Benharref, Ahmed'
'Berraho, Moha'
_publ_section_title
;
 9α-Acetoxy-1β,10α-epoxyparthenolide
;
_journal_coeditor_code           FJ2367
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3239
_journal_paper_doi               10.1107/S1600536810047471
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H22 O6'
_chemical_formula_moiety         'C17 H22 O6'
_chemical_formula_sum            'C17 H22 O6'
_chemical_formula_weight         322.35
_chemical_name_common
;
9α-Acetoxy-1β,10α-epoxyparthenolide
;
_chemical_name_systematic
;
1a,5-dimethyl-8-methylene-9-oxoperhydro-4β,5α-
epoxyoxireno[9,10]cyclodeca[1,2-b]furan-6α-yl acetate
;
_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                 102.039(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2390(3)
_cell_length_b                   10.6482(4)
_cell_length_c                   9.4633(3)
_cell_measurement_reflns_used    12911
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      31.0
_cell_measurement_theta_min      2.2
_cell_volume                     811.96(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 APEX CCD 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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12911
_diffrn_reflns_theta_full        31.05
_diffrn_reflns_theta_max         31.05
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.166
_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     211
_refine_ls_number_reflns         2718
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0381
_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)+(0.0742P)²+0.0491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1146
_reflns_number_gt                2480
_reflns_number_total             2718
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2367.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2228309
_cod_database_fobs_code          2228309
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 C14 0.6599(2) -0.1768(2) 1.05001(19) 0.0485(4) Uani d . 1 . .
H H14A 0.5629 -0.2265 1.0509 0.073 Uiso calc R 1 . .
H H14B 0.7023 -0.1440 1.1450 0.073 Uiso calc R 1 . .
H H14C 0.7431 -0.2282 1.0210 0.073 Uiso calc R 1 . .
C C15 0.6072(3) -0.3610(2) 0.7190(3) 0.0648(5) Uani d . 1 . .
H H15A 0.7103 -0.3776 0.6906 0.097 Uiso calc R 1 . .
H H15B 0.5426 -0.4367 0.7113 0.097 Uiso calc R 1 . .
H H15C 0.6289 -0.3319 0.8172 0.097 Uiso calc R 1 . .
C C1 0.46449(18) -0.06799(17) 0.82978(17) 0.0403(3) Uani d . 1 . .
H H1 0.4716 -0.0145 0.7470 0.048 Uiso calc R 1 . .
C C2 0.3450(2) -0.1765(2) 0.7955(2) 0.0521(4) Uani d . 1 . .
H H2A 0.2344 -0.1481 0.8005 0.063 Uiso calc R 1 . .
H H2B 0.3768 -0.2417 0.8675 0.063 Uiso calc R 1 . .
C C3 0.3418(3) -0.2314(3) 0.6452(3) 0.0644(6) Uani d . 1 . .
H H3A 0.2744 -0.3068 0.6327 0.077 Uiso calc R 1 . .
H H3B 0.2905 -0.1712 0.5724 0.077 Uiso calc R 1 . .
C C4 0.5134(3) -0.2628(2) 0.6226(2) 0.0537(4) Uani d . 1 . .
C C5 0.5937(2) -0.1649(2) 0.55053(18) 0.0501(4) Uani d . 1 . .
H H5 0.5264 -0.0892 0.5253 0.060 Uiso calc R 1 . .
C C6 0.7768(2) -0.14210(17) 0.57840(17) 0.0447(4) Uani d . 1 . .
H H6 0.8377 -0.2171 0.6195 0.054 Uiso calc R 1 . .
C C7 0.82874(19) -0.02749(15) 0.67649(15) 0.0366(3) Uani d . 1 . .
H H7 0.7357 0.0318 0.6601 0.044 Uiso calc R 1 . .
C C8 0.87578(18) -0.05478(18) 0.83958(15) 0.0393(3) Uani d . 1 . .
H H8A 0.8723 -0.1449 0.8535 0.047 Uiso calc R 1 . .
H H8B 0.9894 -0.0279 0.8751 0.047 Uiso calc R 1 . .
C C9 0.76603(17) 0.00787(16) 0.93218(15) 0.0352(3) Uani d . 1 . .
H H9 0.8333 0.0204 1.0295 0.042 Uiso calc R 1 . .
C C10 0.61532(17) -0.06993(15) 0.94522(15) 0.0356(3) Uani d . 1 . .
C C11 0.9645(2) 0.02787(18) 0.61024(19) 0.0464(4) Uani d . 1 . .
C C12 0.9353(3) -0.0178(2) 0.4586(2) 0.0559(5) Uani d . 1 . .
C C13 1.0911(3) 0.1006(3) 0.6654(3) 0.0665(6) Uani d . 1 . .
H H13A 1.1656 0.1250 0.6091 0.080 Uiso calc R 1 . .
H H13B 1.1060 0.1276 0.7607 0.080 Uiso calc R 1 . .
C C16 0.8244(2) 0.22159(18) 0.9006(2) 0.0460(4) Uani d . 1 . .
C C17 0.7628(3) 0.3407(2) 0.8271(2) 0.0597(5) Uani d . 1 . .
H H17A 0.7451 0.4011 0.8976 0.090 Uiso calc R 1 . .
H H17B 0.6600 0.3254 0.7600 0.090 Uiso calc R 1 . .
H H17C 0.8432 0.3726 0.7760 0.090 Uiso calc R 1 . .
O O1 0.5260(3) -0.2753(2) 0.47208(17) 0.0731(5) Uani d . 1 . .
O O2 0.47027(14) -0.00130(14) 0.96360(14) 0.0473(3) Uani d . 1 . .
O O3 0.8194(2) -0.10899(18) 0.44012(14) 0.0622(4) Uani d . 1 . .
O O4 0.9965(3) 0.0176(3) 0.36135(19) 0.0840(6) Uani d . 1 . .
O O5 0.71087(14) 0.12924(11) 0.87370(13) 0.0387(2) Uani d . 1 . .
O O6 0.96035(19) 0.20593(19) 0.9760(2) 0.0711(5) 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
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 ?
O2 C1 C10 . . 59.23(10) ?
O2 C1 C2 . . 117.75(14) ?
C10 C1 C2 . . 124.07(16) ?
O2 C1 H1 . . 114.7 ?
C10 C1 H1 . . 114.7 ?
C2 C1 H1 . . 114.7 ?
C1 C2 C3 . . 112.05(17) ?
C1 C2 H2A . . 109.2 ?
C3 C2 H2A . . 109.2 ?
C1 C2 H2B . . 109.2 ?
C3 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
C4 C3 C2 . . 112.34(16) ?
C4 C3 H3A . . 109.1 ?
C2 C3 H3A . . 109.1 ?
C4 C3 H3B . . 109.1 ?
C2 C3 H3B . . 109.1 ?
H3A C3 H3B . . 107.9 ?
O1 C4 C5 . . 58.81(14) ?
O1 C4 C15 . . 113.58(19) ?
C5 C4 C15 . . 123.53(19) ?
O1 C4 C3 . . 114.76(18) ?
C5 C4 C3 . . 115.6(2) ?
C15 C4 C3 . . 116.7(2) ?
O1 C5 C4 . . 59.90(14) ?
O1 C5 C6 . . 119.44(19) ?
C4 C5 C6 . . 124.49(17) ?
O1 C5 H5 . . 114.1 ?
C4 C5 H5 . . 114.1 ?
C6 C5 H5 . . 114.1 ?
O3 C6 C5 . . 107.57(14) ?
O3 C6 C7 . . 105.02(14) ?
C5 C6 C7 . . 112.25(14) ?
O3 C6 H6 . . 110.6 ?
C5 C6 H6 . . 110.6 ?
C7 C6 H6 . . 110.6 ?
C11 C7 C8 . . 115.88(14) ?
C11 C7 C6 . . 101.30(13) ?
C8 C7 C6 . . 115.81(14) ?
C11 C7 H7 . . 107.8 ?
C8 C7 H7 . . 107.8 ?
C6 C7 H7 . . 107.8 ?
C9 C8 C7 . . 115.78(12) ?
C9 C8 H8A . . 108.3 ?
C7 C8 H8A . . 108.3 ?
C9 C8 H8B . . 108.3 ?
C7 C8 H8B . . 108.3 ?
H8A C8 H8B . . 107.4 ?
O5 C9 C10 . . 108.82(11) ?
O5 C9 C8 . . 110.26(12) ?
C10 C9 C8 . . 113.44(13) ?
O5 C9 H9 . . 108.1 ?
C10 C9 H9 . . 108.1 ?
C8 C9 H9 . . 108.1 ?
O2 C10 C1 . . 59.36(10) ?
O2 C10 C14 . . 113.50(13) ?
C1 C10 C14 . . 123.48(15) ?
O2 C10 C9 . . 116.46(13) ?
C1 C10 C9 . . 120.62(13) ?
C14 C10 C9 . . 112.01(13) ?
C13 C11 C12 . . 122.04(18) ?
C13 C11 C7 . . 131.20(19) ?
C12 C11 C7 . . 106.75(17) ?
O4 C12 O3 . . 121.8(2) ?
O4 C12 C11 . . 129.0(3) ?
O3 C12 C11 . . 109.18(15) ?
C11 C13 H13A . . 120.0 ?
C11 C13 H13B . . 120.0 ?
H13A C13 H13B . . 120.0 ?
O6 C16 O5 . . 122.27(19) ?
O6 C16 C17 . . 125.43(18) ?
O5 C16 C17 . . 112.30(16) ?
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 ?
C5 O1 C4 . . 61.28(13) ?
C10 O2 C1 . . 61.41(10) ?
C12 O3 C6 . . 110.63(14) ?
C16 O5 C9 . . 115.58(13) ?
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
C14 C10 . 1.504(2) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 C4 . 1.493(3) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C1 O2 . 1.444(2) ?
C1 C10 . 1.474(2) ?
C1 C2 . 1.508(3) ?
C1 H1 . 0.9800 ?
C2 C3 . 1.534(3) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.511(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 O1 . 1.456(3) ?
C4 C5 . 1.476(3) ?
C5 O1 . 1.439(3) ?
C5 C6 . 1.496(3) ?
C5 H5 . 0.9800 ?
C6 O3 . 1.467(2) ?
C6 C7 . 1.539(2) ?
C6 H6 . 0.9800 ?
C7 C11 . 1.511(2) ?
C7 C8 . 1.5386(19) ?
C7 H7 . 0.9800 ?
C8 C9 . 1.537(2) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 O5 . 1.442(2) ?
C9 C10 . 1.519(2) ?
C9 H9 . 0.9800 ?
C10 O2 . 1.4419(18) ?
C11 C13 . 1.316(3) ?
C11 C12 . 1.486(3) ?
C12 O4 . 1.199(2) ?
C12 O3 . 1.348(3) ?
C13 H13A . 0.9300 ?
C13 H13B . 0.9300 ?
C16 O6 . 1.207(3) ?
C16 O5 . 1.345(2) ?
C16 C17 . 1.484(3) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656348
