#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2220705.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_2220705
loop_
_publ_author_name
'Gul, Waseem'
'Carvalho, Paulo'
'Galal, Ahmed'
'Avery, Mitchell A.'
'El Sohly, Mahmoud A.'
_publ_section_title
;
5-{[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-3,6,9-Trimethylperhydro-3,12-epoxy-1,2-dioxepino[4,3-i]isochromen-10-yl]oxymethyl}benzene-1,3-diol
;
_journal_coeditor_code BI2336
_journal_issue 2
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o358
_journal_page_last o359
_journal_volume 65
_journal_year 2009
_chemical_formula_iupac 'C22 H30 O7'
_chemical_formula_moiety 'C22 H30 O7'
_chemical_formula_sum 'C22 H30 O7'
_chemical_formula_weight 406.46
_chemical_name_common
'12-(3-hydroxy,5-hydroxymethyl)phenoxy dihydroartemisinin'
_chemical_name_systematic
;
5-{[(3R,5aS,6R,8aS,9R,10S,12R,
12aR)-3,6,9-Trimethylperhydro-3,12-epoxy-1,2-dioxepino[4,3-
i]isochromen-10-yl]oxymethyl}benzene-1,3-diol
;
_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 113.140(10)
_cell_angle_gamma 90.00
_cell_formula_units_Z 2
_cell_length_a 10.3088(2)
_cell_length_b 10.2844(2)
_cell_length_c 10.3218(3)
_cell_measurement_reflns_used 9920
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 68.92
_cell_measurement_theta_min 4.30
_cell_volume 1006.27(9)
_computing_cell_refinement 'SAINT (Bruker, 2005)'
_computing_data_collection 'APEX2 (Bruker, 2005)'
_computing_data_reduction 'SAINT (Bruker, 2005)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type 'Bruker APEXII CCD'
_diffrn_measurement_method '\f and \w'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_reflns_av_R_equivalents 0.0187
_diffrn_reflns_av_sigmaI/netI 0.0144
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_number 15943
_diffrn_reflns_theta_full 69.33
_diffrn_reflns_theta_max 69.33
_diffrn_reflns_theta_min 4.66
_diffrn_standards_number 0
_exptl_absorpt_coefficient_mu 0.820
_exptl_absorpt_correction_type none
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.341
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description plate
_exptl_crystal_F_000 436
_exptl_crystal_size_max 0.23
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.08
_refine_diff_density_max 0.245
_refine_diff_density_min -0.217
_refine_ls_abs_structure_details 'Flack (1983), 1623 Friedel pairs'
_refine_ls_abs_structure_Flack 0.04(10)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.078
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 267
_refine_ls_number_reflns 3623
_refine_ls_number_restraints 1
_refine_ls_restrained_S_all 1.077
_refine_ls_R_factor_all 0.0259
_refine_ls_R_factor_gt 0.0258
_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/[\s^2^(Fo^2^)+(0.0416P)^2^+0.199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0687
_refine_ls_wR_factor_ref 0.0688
_reflns_number_gt 3604
_reflns_number_total 3623
_reflns_threshold_expression I>2\s(I)
_[local]_cod_data_source_file bi2336.cif
_[local]_cod_data_source_block I
_[local]_cod_cif_authors_sg_H-M 'P 21'
_cod_original_cell_volume 1006.29(9)
_cod_database_code 2220705
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 O4 0.24620(9) 0.53498(9) 0.32197(9) 0.01671(19) Uani d . 1
O O1 -0.02356(10) 0.56559(9) 0.09293(9) 0.0177(2) Uani d . 1
O O6 0.41598(11) 0.67491(10) 1.04175(10) 0.0238(2) Uani d . 1
H H6 0.3735 0.6057 1.0194 0.036 Uiso calc R 1
O O5 0.34731(9) 0.70855(9) 0.47383(9) 0.01720(19) Uani d . 1
O O3 0.07779(9) 0.40591(9) 0.33999(9) 0.0184(2) Uani d . 1
O O7 0.71639(10) 0.95263(9) 0.93260(10) 0.0213(2) Uani d . 1
H H7 0.7608 0.9578 0.8820 0.032 Uiso calc R 1
O O2 0.02421(10) 0.42912(9) 0.10142(9) 0.0191(2) Uani d . 1
C C18 0.58553(13) 0.79300(13) 0.75672(13) 0.0177(3) Uani d . 1
H H18 0.6249 0.8215 0.6946 0.021 Uiso calc R 1
C C1 -0.01197(14) 0.36064(14) 0.20186(14) 0.0204(3) Uani d . 1
C C20 0.56095(14) 0.81251(13) 0.97930(13) 0.0178(3) Uani d . 1
H H20 0.5828 0.8554 1.0646 0.021 Uiso calc R 1
C C10 0.31061(13) 0.66001(13) 0.33627(13) 0.0172(3) Uani d . 1
H H10 0.3973 0.6505 0.3195 0.021 Uiso calc R 1
C C8 0.06357(14) 0.75832(13) 0.22778(13) 0.0166(3) Uani d . 1
H H8 0.0018 0.7965 0.1376 0.020 Uiso calc R 1
C C4 -0.13890(13) 0.62313(15) 0.24865(13) 0.0193(3) Uani d . 1
H H4 -0.2079 0.6579 0.1599 0.023 Uiso calc R 1
C C11 0.11686(13) 0.53590(13) 0.34304(13) 0.0158(3) Uani d . 1
H H11 0.1353 0.5713 0.4368 0.019 Uiso calc R 1
C C12 0.00544(13) 0.62013(13) 0.23280(13) 0.0161(3) Uani d . 1
C C22 0.43232(13) 0.64640(13) 0.81424(14) 0.0184(3) Uani d . 1
H H22 0.3703 0.5763 0.7905 0.022 Uiso calc R 1
C C7 0.05456(14) 0.84730(14) 0.34327(14) 0.0198(3) Uani d . 1
H H7A 0.1191 0.8161 0.4346 0.024 Uiso calc R 1
H H7B 0.0834 0.9345 0.3305 0.024 Uiso calc R 1
C C5 -0.13896(13) 0.71641(15) 0.36552(13) 0.0221(3) Uani d . 1
H H5 -0.0685 0.6848 0.4551 0.026 Uiso calc R 1
C C15 0.28159(15) 0.88607(14) 0.23539(15) 0.0233(3) Uani d . 1
H H15A 0.3043 0.9221 0.3276 0.035 Uiso calc R 1
H H15B 0.2171 0.9428 0.1660 0.035 Uiso calc R 1
H H15C 0.3662 0.8771 0.2183 0.035 Uiso calc R 1
C C14 -0.28261(14) 0.71858(18) 0.37886(15) 0.0297(3) Uani d . 1
H H14A -0.2827 0.7861 0.4430 0.044 Uiso calc R 1
H H14B -0.2986 0.6362 0.4137 0.044 Uiso calc R 1
H H14C -0.3561 0.7348 0.2881 0.044 Uiso calc R 1
C C17 0.48996(13) 0.69005(13) 0.72052(13) 0.0174(3) Uani d . 1
C C6 -0.09417(15) 0.85158(15) 0.34012(14) 0.0231(3) Uani d . 1
H H6A -0.0971 0.9106 0.4123 0.028 Uiso calc R 1
H H6B -0.1590 0.8836 0.2493 0.028 Uiso calc R 1
C C16 0.44908(14) 0.62693(14) 0.57838(14) 0.0200(3) Uani d . 1
H H16A 0.5318 0.6160 0.5566 0.024 Uiso calc R 1
H H16B 0.4087 0.5418 0.5788 0.024 Uiso calc R 1
C C9 0.21337(13) 0.75281(13) 0.22646(13) 0.0178(3) Uani d . 1
H H9 0.2017 0.7167 0.1347 0.021 Uiso calc R 1
C C21 0.46825(13) 0.70848(14) 0.94374(13) 0.0186(3) Uani d . 1
C C19 0.62111(13) 0.85242(13) 0.88701(14) 0.0173(3) Uani d . 1
C C3 -0.19196(14) 0.48755(15) 0.26635(14) 0.0237(3) Uani d . 1
H H3A -0.1469 0.4632 0.3649 0.028 Uiso calc R 1
H H3B -0.2925 0.4932 0.2432 0.028 Uiso calc R 1
C C2 -0.16688(14) 0.37942(15) 0.17856(14) 0.0234(3) Uani d . 1
H H2A -0.2207 0.3982 0.0797 0.028 Uiso calc R 1
H H2B -0.2024 0.2986 0.2004 0.028 Uiso calc R 1
C C13 0.02745(16) 0.22097(15) 0.19089(15) 0.0262(3) Uani d . 1
H H13A -0.0393 0.1835 0.1055 0.039 Uiso calc R 1
H H13B 0.0267 0.1729 0.2703 0.039 Uiso calc R 1
H H13C 0.1201 0.2176 0.1899 0.039 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O4 0.0160(4) 0.0163(5) 0.0179(4) -0.0009(3) 0.0068(4) -0.0024(3)
O1 0.0225(5) 0.0173(5) 0.0130(4) -0.0007(4) 0.0067(4) -0.0007(4)
O6 0.0285(5) 0.0254(5) 0.0221(5) -0.0052(4) 0.0149(4) 0.0005(4)
O5 0.0169(4) 0.0187(5) 0.0140(4) 0.0006(4) 0.0039(3) -0.0015(3)
O3 0.0215(5) 0.0181(5) 0.0140(4) -0.0030(4) 0.0051(4) -0.0005(3)
O7 0.0232(5) 0.0217(5) 0.0232(5) -0.0058(4) 0.0138(4) -0.0047(4)
O2 0.0234(5) 0.0183(5) 0.0170(4) -0.0016(4) 0.0094(4) -0.0024(4)
C18 0.0191(6) 0.0192(7) 0.0165(6) 0.0030(5) 0.0088(5) 0.0022(5)
C1 0.0246(7) 0.0215(7) 0.0146(6) -0.0075(5) 0.0072(5) -0.0028(5)
C20 0.0185(6) 0.0203(7) 0.0145(6) 0.0029(5) 0.0063(5) -0.0002(5)
C10 0.0165(6) 0.0197(7) 0.0162(6) -0.0034(5) 0.0074(5) -0.0032(5)
C8 0.0192(6) 0.0167(7) 0.0134(6) 0.0021(5) 0.0060(5) 0.0014(5)
C4 0.0149(6) 0.0279(7) 0.0146(6) 0.0008(5) 0.0052(5) 0.0002(5)
C11 0.0177(6) 0.0158(7) 0.0149(6) -0.0018(5) 0.0075(5) -0.0022(5)
C12 0.0176(6) 0.0202(7) 0.0109(6) -0.0015(5) 0.0060(5) -0.0016(5)
C22 0.0147(6) 0.0170(7) 0.0220(6) -0.0001(5) 0.0055(5) 0.0005(5)
C7 0.0229(7) 0.0170(7) 0.0185(6) 0.0017(5) 0.0072(5) -0.0011(5)
C5 0.0178(6) 0.0329(8) 0.0153(6) 0.0039(6) 0.0063(5) 0.0005(6)
C15 0.0253(7) 0.0239(8) 0.0213(7) -0.0053(6) 0.0097(6) -0.0003(6)
C14 0.0222(7) 0.0464(10) 0.0225(7) 0.0053(7) 0.0112(6) -0.0023(7)
C17 0.0150(5) 0.0182(7) 0.0174(6) 0.0050(5) 0.0045(5) 0.0015(5)
C6 0.0249(7) 0.0269(8) 0.0177(6) 0.0080(6) 0.0086(5) -0.0015(6)
C16 0.0190(6) 0.0200(7) 0.0190(6) 0.0032(5) 0.0053(5) 0.0005(5)
C9 0.0195(6) 0.0209(7) 0.0139(6) -0.0036(5) 0.0075(5) -0.0016(5)
C21 0.0159(6) 0.0215(7) 0.0189(6) 0.0038(5) 0.0075(5) 0.0044(5)
C19 0.0147(6) 0.0164(7) 0.0199(6) 0.0019(5) 0.0058(5) 0.0023(5)
C3 0.0178(6) 0.0346(8) 0.0196(6) -0.0045(6) 0.0082(5) 0.0006(6)
C2 0.0227(7) 0.0279(8) 0.0190(6) -0.0101(6) 0.0075(5) -0.0011(5)
C13 0.0335(7) 0.0225(8) 0.0213(7) -0.0056(6) 0.0094(6) -0.0031(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C10 O4 C11 113.64(9)
C12 O1 O2 111.75(9)
C21 O6 H6 109.5
C10 O5 C16 112.09(10)
C11 O3 C1 113.63(10)
C19 O7 H7 109.5
C1 O2 O1 109.72(9)
C19 C18 C17 118.94(12)
C19 C18 H18 120.5
C17 C18 H18 120.5
O2 C1 O3 108.18(10)
O2 C1 C13 105.17(11)
O3 C1 C13 107.17(11)
O2 C1 C2 112.33(11)
O3 C1 C2 109.88(10)
C13 C1 C2 113.79(11)
C21 C20 C19 119.65(12)
C21 C20 H20 120.2
C19 C20 H20 120.2
O5 C10 O4 110.67(10)
O5 C10 C9 111.50(10)
O4 C10 C9 110.18(10)
O5 C10 H10 108.1
O4 C10 H10 108.1
C9 C10 H10 108.1
C7 C8 C9 113.15(11)
C7 C8 C12 112.23(10)
C9 C8 C12 111.46(10)
C7 C8 H8 106.5
C9 C8 H8 106.5
C12 C8 H8 106.5
C3 C4 C5 111.25(11)
C3 C4 C12 113.19(11)
C5 C4 C12 112.84(10)
C3 C4 H4 106.3
C5 C4 H4 106.3
C12 C4 H4 106.3
O3 C11 O4 105.56(10)
O3 C11 C12 113.63(10)
O4 C11 C12 111.25(10)
O3 C11 H11 108.8
O4 C11 H11 108.8
C12 C11 H11 108.8
O1 C12 C11 108.60(10)
O1 C12 C8 104.45(9)
C11 C12 C8 110.91(10)
O1 C12 C4 106.09(10)
C11 C12 C4 113.69(10)
C8 C12 C4 112.48(11)
C17 C22 C21 119.54(12)
C17 C22 H22 120.2
C21 C22 H22 120.2
C6 C7 C8 111.64(11)
C6 C7 H7A 109.3
C8 C7 H7A 109.3
C6 C7 H7B 109.3
C8 C7 H7B 109.3
H7A C7 H7B 108.0
C6 C5 C14 111.72(12)
C6 C5 C4 109.92(11)
C14 C5 C4 112.02(11)
C6 C5 H5 107.7
C14 C5 H5 107.7
C4 C5 H5 107.7
C9 C15 H15A 109.5
C9 C15 H15B 109.5
H15A C15 H15B 109.5
C9 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C5 C14 H14A 109.5
C5 C14 H14B 109.5
H14A C14 H14B 109.5
C5 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C22 C17 C18 120.53(12)
C22 C17 C16 120.35(12)
C18 C17 C16 119.12(12)
C5 C6 C7 109.99(11)
C5 C6 H6A 109.7
C7 C6 H6A 109.7
C5 C6 H6B 109.7
C7 C6 H6B 109.7
H6A C6 H6B 108.2
O5 C16 C17 108.73(10)
O5 C16 H16A 109.9
C17 C16 H16A 109.9
O5 C16 H16B 109.9
C17 C16 H16B 109.9
H16A C16 H16B 108.3
C10 C9 C15 111.45(11)
C10 C9 C8 112.57(10)
C15 C9 C8 113.79(11)
C10 C9 H9 106.1
C15 C9 H9 106.1
C8 C9 H9 106.1
O6 C21 C20 115.57(12)
O6 C21 C22 124.17(12)
C20 C21 C22 120.26(12)
O7 C19 C20 116.06(11)
O7 C19 C18 122.91(11)
C20 C19 C18 121.03(12)
C2 C3 C4 116.22(11)
C2 C3 H3A 108.2
C4 C3 H3A 108.2
C2 C3 H3B 108.2
C4 C3 H3B 108.2
H3A C3 H3B 107.4
C3 C2 C1 114.21(11)
C3 C2 H2A 108.7
C1 C2 H2A 108.7
C3 C2 H2B 108.7
C1 C2 H2B 108.7
H2A C2 H2B 107.6
C1 C13 H13A 109.5
C1 C13 H13B 109.5
H13A C13 H13B 109.5
C1 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C10 1.4280(16)
O4 C11 1.4328(15)
O1 C12 1.4660(15)
O1 O2 1.4785(13)
O6 C21 1.3644(16)
O6 H6 0.820
O5 C10 1.4092(15)
O5 C16 1.4423(16)
O3 C11 1.3930(17)
O3 C1 1.4384(15)
O7 C19 1.3730(16)
O7 H7 0.820
O2 C1 1.4191(16)
C18 C19 1.3888(18)
C18 C17 1.3936(19)
C18 H18 0.930
C1 C13 1.509(2)
C1 C2 1.5308(19)
C20 C21 1.3845(19)
C20 C19 1.3874(18)
C20 H20 0.930
C10 C9 1.5190(18)
C10 H10 0.980
C8 C7 1.5344(18)
C8 C9 1.5506(17)
C8 C12 1.5512(18)
C8 H8 0.980
C4 C3 1.535(2)
C4 C5 1.5415(19)
C4 C12 1.5598(16)
C4 H4 0.980
C11 C12 1.5289(17)
C11 H11 0.980
C22 C17 1.3936(19)
C22 C21 1.3937(19)
C22 H22 0.930
C7 C6 1.5214(19)
C7 H7A 0.970
C7 H7B 0.970
C5 C6 1.520(2)
C5 C14 1.5403(17)
C5 H5 0.980
C15 C9 1.5266(19)
C15 H15A 0.960
C15 H15B 0.960
C15 H15C 0.960
C14 H14A 0.960
C14 H14B 0.960
C14 H14C 0.960
C17 C16 1.5052(18)
C6 H6A 0.970
C6 H6B 0.970
C16 H16A 0.970
C16 H16B 0.970
C9 H9 0.980
C3 C2 1.520(2)
C3 H3A 0.970
C3 H3B 0.970
C2 H2A 0.970
C2 H2B 0.970
C13 H13A 0.960
C13 H13B 0.960
C13 H13C 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_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O6 H6 O7 2_647 0.82 1.99 2.7279(14) 150.2
O7 H7 O2 2_656 0.82 2.18 2.8409(13) 138.4
O7 H7 O4 2_656 0.82 2.22 2.9269(13) 143.8