##############################################################################
# #
# This CIF contains the data in a paper accepted for publication in #
# Acta Crystallographica Section E. It conforms to the requirements of #
# Notes for Authors for Acta Crystallographica Section E, and has been #
# peer reviewed under the auspices of the IUCr Commission on Journals. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary is obtainable from #
# ftp://ftp.iucr.org/pub/cif_core.dic. #
# #
# Software is freely available for graphical display of the structure(s) #
# in this CIF. For information consult the CIF software page #
# http://www.iucr.org/resources/cif/software. #
# #
# This file may be used for bona fide research purposes within the #
# scientific community so long as proper attribution is given to the journal #
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data_global
_audit_creation_method SHELXL-97
_journal_date_recd_electronic 2012-05-17
_journal_date_accepted 2012-05-17
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2012
_journal_volume 68
_journal_issue 6
_journal_page_first o1874
_journal_page_last o1874
_journal_paper_category QO
_journal_paper_doi 10.1107/S1600536812022623
_journal_coeditor_code XU5544
_publ_contact_author
;
Dr. Seik Weng Ng
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
_publ_contact_author_email seikweng@um.edu.my
_publ_contact_author_fax '03 7967 4193'
_publ_contact_author_phone '03 7967 6778'
_publ_section_title
;
(3R,4S)-3,4,8-Trihydroxy-1,2,3,4-tetrahydronaphthalen-1-one
monohydrate from Embellisia eureka
;
loop_
_publ_author_name
_publ_author_address
'Ouchbani, Tarik'
;
Laboratoire de Chimie Organique H\'et\'erocyclique
P\^ole de Comp\'etences Pharmacochimie
Universit\'e Mohammed V-Agdal
BP 1014 Avenue Ibn Batout
Rabat
Morocco
;
'Zouihri, Hafid'
;
CNRST Division UATRS
Angle Allal Fassi/ FAR
BP 8027 Hay Riad
Rabat
Morocco
;
'Essassi, El Mokhtar'
;
Laboratoire de Chimie Organique H\'et\'erocyclique
P\^ole de Comp\'etences Pharmacochimie
Universit\'e Mohammed V-Agdal
BP 1014 Avenue Ibn Batout
Rabat
Morocco
;
'Proksch, Peter'
;
Institut f\"ur Pharmazeutische Biologie und Biotechnologie
Heinrich Heine University D\"usseldorf
Geb\"aude 26.23, Universit\"atsstrasse 1
40225 D\"usseldorf
Germany
;
'Ng, Seik Weng'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
Chemistry Department
King Abdulaziz University
PO Box 80203 Jeddah
Saudi Arabia
;
data_I
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(3R,4S)-3,4,8-Trihydroxy-1,2,3,4-tetrahydronaphthalen-1-one
monohydrate
;
_chemical_name_common ?
_chemical_formula_moiety 'C10 H10 O4, H2 O'
_chemical_formula_sum 'C10 H12 O5'
_chemical_formula_iupac 'C10 H10 O4, H2 O'
_chemical_formula_weight 212.20
_chemical_melting_point ?
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'
_symmetry_space_group_name_Hall 'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 4.6430(4)
_cell_length_b 14.3904(11)
_cell_length_c 14.4976(10)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 968.65(13)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 1057
_cell_measurement_theta_min 2.8176
_cell_measurement_theta_max 21.7879
_cell_measurement_temperature 293(2)
_exptl_crystal_description prism
_exptl_crystal_colour brown
_exptl_crystal_size_max 0.31
_exptl_crystal_size_mid 0.28
_exptl_crystal_size_min 0.24
_exptl_crystal_density_diffrn 1.455
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 448
_exptl_absorpt_coefficient_mu 0.118
_exptl_absorpt_correction_type none
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX DUO'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 6331
_diffrn_reflns_av_R_equivalents 0.0630
_diffrn_reflns_av_sigmaI/netI 0.0608
_diffrn_reflns_theta_min 2.81
_diffrn_reflns_theta_max 27.49
_diffrn_reflns_theta_full 27.49
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_h_max 5
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 18
_diffrn_standards_number 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_decay_% 0
_reflns_number_total 1320
_reflns_number_gt 916
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0738
_refine_ls_R_factor_gt 0.0388
_refine_ls_wR_factor_gt 0.0832
_refine_ls_wR_factor_ref 0.0962
_refine_ls_goodness_of_fit_ref 0.986
_refine_ls_restrained_S_all 0.984
_refine_ls_number_reflns 1320
_refine_ls_number_parameters 156
_refine_ls_number_restraints 5
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0507P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.001
_refine_diff_density_max 0.208
_refine_diff_density_min -0.209
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
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'
_computing_data_collection 'APEX2 (Bruker, 2010)'
_computing_cell_refinement 'SAINT (Bruker, 2010)'
_computing_data_reduction 'SAINT (Bruker, 2010)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'X-SEED (Barbour, 2001)'
_computing_publication_material 'publCIF (Westrip, 2010)'
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5051(5) 0.75199(14) 0.74392(14) 0.0280(6) Uani d D 1 1 . .
O O2 0.1740(5) 0.83227(14) 0.62424(12) 0.0281(5) Uani d . 1 1 . .
O O3 0.1933(5) 1.08380(14) 0.69719(15) 0.0262(5) Uani d D 1 1 . .
O O4 -0.0651(5) 1.10191(16) 0.87414(16) 0.0318(5) Uani d D 1 1 . .
O O1w 0.0565(5) 0.82560(15) 0.43458(14) 0.0268(5) Uani d D 1 1 . .
C C1 0.1862(7) 0.8812(2) 0.77911(18) 0.0198(6) Uani d . 1 1 . .
C C2 0.3877(7) 0.81217(18) 0.80514(18) 0.0226(7) Uani d . 1 1 . .
C C3 0.4788(7) 0.8053(2) 0.89602(18) 0.0270(7) Uani d . 1 1 . .
H H3A 0.6084 0.7592 0.9134 0.032 Uiso calc R 1 1 . .
C C4 0.3753(7) 0.8673(2) 0.96024(19) 0.0278(8) Uani d . 1 1 . .
H H4A 0.4351 0.8622 1.0213 0.033 Uiso calc R 1 1 . .
C C5 0.1843(7) 0.9371(2) 0.9362(2) 0.0247(7) Uani d . 1 1 . .
H H5A 0.1202 0.9787 0.9809 0.030 Uiso calc R 1 1 . .
C C6 0.0881(7) 0.94556(19) 0.8461(2) 0.0211(6) Uani d . 1 1 . .
C C7 -0.1173(7) 1.02214(19) 0.8181(2) 0.0244(7) Uani d . 1 1 . .
H H7 -0.3147 1.0008 0.8293 0.029 Uiso calc R 1 1 . .
C C8 -0.0888(7) 1.0480(2) 0.7169(2) 0.0235(7) Uani d . 1 1 . .
H H8 -0.2352 1.0942 0.7004 0.028 Uiso calc R 1 1 . .
C C9 -0.1250(6) 0.96220(19) 0.6583(2) 0.0236(7) Uani d . 1 1 . .
H H9A -0.3192 0.9385 0.6658 0.028 Uiso calc R 1 1 . .
H H9B -0.0993 0.9786 0.5940 0.028 Uiso calc R 1 1 . .
C C10 0.0858(6) 0.88749(19) 0.68341(18) 0.0193(6) Uani d . 1 1 . .
H H1 0.439(8) 0.761(2) 0.6908(13) 0.049(12) Uiso d D 1 1 . .
H H2 0.228(12) 1.1339(18) 0.725(3) 0.103(19) Uiso d D 1 1 . .
H H3 -0.228(4) 1.118(3) 0.895(2) 0.061(13) Uiso d D 1 1 . .
H H4 0.071(10) 0.821(2) 0.4923(8) 0.060(13) Uiso d D 1 1 . .
H H5 0.212(4) 0.848(2) 0.414(2) 0.039(11) Uiso d D 1 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
O1 0.0361(14) 0.0245(12) 0.0236(11) 0.0091(10) -0.0056(11) -0.0015(10)
O2 0.0319(12) 0.0308(11) 0.0215(10) 0.0076(11) -0.0046(10) -0.0056(9)
O3 0.0207(11) 0.0228(12) 0.0351(12) -0.0052(10) 0.0051(10) -0.0006(10)
O4 0.0180(11) 0.0354(13) 0.0420(13) 0.0034(11) 0.0007(11) -0.0182(11)
O1w 0.0195(12) 0.0378(13) 0.0231(11) -0.0054(11) -0.0032(10) 0.0044(10)
C1 0.0176(15) 0.0199(14) 0.0220(14) -0.0065(12) 0.0019(12) 0.0013(12)
C2 0.0261(17) 0.0187(15) 0.0229(14) -0.0045(13) -0.0005(13) -0.0019(12)
C3 0.034(2) 0.0230(16) 0.0243(15) -0.0021(14) -0.0067(14) 0.0071(14)
C4 0.034(2) 0.0321(17) 0.0175(14) -0.0094(15) -0.0003(14) 0.0024(13)
C5 0.0224(16) 0.0282(17) 0.0235(15) -0.0068(14) 0.0066(14) -0.0030(13)
C6 0.0153(14) 0.0246(15) 0.0234(15) -0.0070(13) 0.0052(13) -0.0015(12)
C7 0.0173(16) 0.0263(16) 0.0298(16) -0.0011(13) 0.0007(14) -0.0069(14)
C8 0.0157(14) 0.0209(15) 0.0340(16) 0.0029(13) 0.0003(13) 0.0015(13)
C9 0.0158(16) 0.0299(16) 0.0252(16) 0.0005(13) -0.0031(13) -0.0006(13)
C10 0.0155(14) 0.0215(14) 0.0211(13) -0.0048(13) -0.0004(13) 0.0016(12)
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
O1 C2 . 1.355(3) ?
O1 H1 . 0.840(10) ?
O2 C10 . 1.239(3) ?
O3 C8 . 1.436(4) ?
O3 H2 . 0.841(10) ?
O4 C7 . 1.427(3) ?
O4 H3 . 0.846(10) ?
O1w H4 . 0.842(10) ?
O1w H5 . 0.846(10) ?
C1 C6 . 1.417(4) ?
C1 C2 . 1.416(4) ?
C1 C10 . 1.466(4) ?
C2 C3 . 1.387(4) ?
C3 C4 . 1.377(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.384(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.386(4) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.513(4) ?
C7 C8 . 1.520(4) ?
C7 H7 . 0.9800 ?
C8 C9 . 1.508(4) ?
C8 H8 . 0.9800 ?
C9 C10 . 1.498(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
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
C2 O1 H1 . . 111(3) ?
C8 O3 H2 . . 113(4) ?
C7 O4 H3 . . 106(3) ?
H4 O1w H5 . . 109(4) ?
C6 C1 C2 . . 119.2(2) ?
C6 C1 C10 . . 120.4(3) ?
C2 C1 C10 . . 120.3(2) ?
O1 C2 C3 . . 117.0(3) ?
O1 C2 C1 . . 122.7(2) ?
C3 C2 C1 . . 120.3(3) ?
C4 C3 C2 . . 119.3(3) ?
C4 C3 H3A . . 120.3 ?
C2 C3 H3A . . 120.3 ?
C3 C4 C5 . . 121.6(3) ?
C3 C4 H4A . . 119.2 ?
C5 C4 H4A . . 119.2 ?
C4 C5 C6 . . 120.5(3) ?
C4 C5 H5A . . 119.8 ?
C6 C5 H5A . . 119.8 ?
C5 C6 C1 . . 119.0(3) ?
C5 C6 C7 . . 121.3(3) ?
C1 C6 C7 . . 119.6(3) ?
O4 C7 C6 . . 109.1(2) ?
O4 C7 C8 . . 109.7(2) ?
C6 C7 C8 . . 112.5(3) ?
O4 C7 H7 . . 108.5 ?
C6 C7 H7 . . 108.5 ?
C8 C7 H7 . . 108.5 ?
O3 C8 C9 . . 106.4(2) ?
O3 C8 C7 . . 111.0(2) ?
C9 C8 C7 . . 109.5(2) ?
O3 C8 H8 . . 109.9 ?
C9 C8 H8 . . 109.9 ?
C7 C8 H8 . . 109.9 ?
C10 C9 C8 . . 112.2(2) ?
C10 C9 H9A . . 109.2 ?
C8 C9 H9A . . 109.2 ?
C10 C9 H9B . . 109.2 ?
C8 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
O2 C10 C1 . . 120.7(3) ?
O2 C10 C9 . . 120.5(2) ?
C1 C10 C9 . . 118.8(3) ?
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
C6 C1 C2 O1 . . . . -175.8(3) ?
C10 C1 C2 O1 . . . . 2.8(4) ?
C6 C1 C2 C3 . . . . 2.6(4) ?
C10 C1 C2 C3 . . . . -178.9(3) ?
O1 C2 C3 C4 . . . . 177.3(3) ?
C1 C2 C3 C4 . . . . -1.2(4) ?
C2 C3 C4 C5 . . . . -0.6(5) ?
C3 C4 C5 C6 . . . . 1.0(5) ?
C4 C5 C6 C1 . . . . 0.5(4) ?
C4 C5 C6 C7 . . . . -179.1(3) ?
C2 C1 C6 C5 . . . . -2.2(4) ?
C10 C1 C6 C5 . . . . 179.2(3) ?
C2 C1 C6 C7 . . . . 177.4(3) ?
C10 C1 C6 C7 . . . . -1.1(4) ?
C5 C6 C7 O4 . . . . 31.2(4) ?
C1 C6 C7 O4 . . . . -148.4(3) ?
C5 C6 C7 C8 . . . . 153.2(3) ?
C1 C6 C7 C8 . . . . -26.4(4) ?
O4 C7 C8 O3 . . . . 59.1(3) ?
C6 C7 C8 O3 . . . . -62.5(3) ?
O4 C7 C8 C9 . . . . 176.3(2) ?
C6 C7 C8 C9 . . . . 54.7(3) ?
O3 C8 C9 C10 . . . . 63.4(3) ?
C7 C8 C9 C10 . . . . -56.7(3) ?
C6 C1 C10 O2 . . . . 178.9(3) ?
C2 C1 C10 O2 . . . . 0.4(4) ?
C6 C1 C10 C9 . . . . -0.8(4) ?
C2 C1 C10 C9 . . . . -179.3(3) ?
C8 C9 C10 O2 . . . . -149.4(3) ?
C8 C9 C10 C1 . . . . 30.4(3) ?
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
O1 H1 O2 . 0.840(10)
1.87(3) 2.590(3) 143(3)
O1 H1 O1w 4_566 0.840(10)
2.27(3) 2.829(3) 124(3)
O3 H2 O1 3_656 0.840(10)
2.15(3) 2.924(3) 153(5)
O4 H3 O1w 2_475 0.850(10)
1.820(10)
2.657(3) 170(4)
O1w H4 O2 . 0.840(10)
1.980(10)
2.805(3) 167(4)
O1w H5 O4 2_574 0.850(10)
1.880(10)
2.726(3) 177(3)