##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-02-08
_journal_date_accepted     2010-02-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      3
_journal_page_first     o620
_journal_page_last     o620
_journal_paper_category     QO
_journal_coeditor_code     BT5194
_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
;
Meranzin hydrate from <i>Muraya paniculata</i>
;
loop_
    _publ_author_name
    _publ_author_address
    'Julaeha, Euis'
;
Department of Chemistry
Faculty of Mathematics and Natural Sciences
Padjadjaran University
Jatinangor 45363
West Java
Indonesia
;
    'Supratman, Unang'
;
Department of Chemistry
Faculty of Mathematics and Natural Sciences
Padjadjaran University
Jatinangor 45363
West Java
Indonesia
;
    'Mukhtar, Mat Ropi'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
    'Awang, Khalijah'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
    'Ng, Seik Weng'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
8-[2,3-dihydroxy-3-methylbutyl]-7-methoxy-2<i>H</i>-1-benzopyran-2-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H18 O5'
_chemical_formula_sum     'C15 H18 O5'
_chemical_formula_iupac     'C15 H18 O5'
_chemical_formula_weight     278.29
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     5.8061(7)
_cell_length_b     10.5146(13)
_cell_length_c     11.4477(14)
_cell_angle_alpha     90.00
_cell_angle_beta     91.547(2)
_cell_angle_gamma     90.00
_cell_volume     698.61(15)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1731
_cell_measurement_theta_min     2.6
_cell_measurement_theta_max     22.3
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.323
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     296
_exptl_absorpt_coefficient_mu     0.099
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_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 SMART APEX'
_diffrn_measurement_method     \w
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6694
_diffrn_reflns_av_R_equivalents     0.0400
_diffrn_reflns_av_sigmaI/netI     0.0360
_diffrn_reflns_theta_min     1.78
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     1699
_reflns_number_gt     1338
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0513
_refine_ls_R_factor_gt     0.0383
_refine_ls_wR_factor_gt     0.0926
_refine_ls_wR_factor_ref     0.1015
_refine_ls_goodness_of_fit_ref     1.004
_refine_ls_restrained_S_all     1.003
_refine_ls_number_reflns     1699
_refine_ls_number_parameters     192
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[\s^2^(Fo^2^)+(0.0603P)^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     0.123
_refine_diff_density_min     -0.158
_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, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_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_disorder_assembly
    _atom_site_disorder_group
    O O1 1.4383(3) 0.50000(16) 0.83522(15) 0.0436(4) Uani d . 1 . .
    O O2 1.7272(3) 0.51296(19) 0.96204(18) 0.0592(5) Uani d . 1 . .
    O O3 0.8098(4) 0.4410(2) 0.57958(18) 0.0677(6) Uani d . 1 . .
    O O4 1.0213(3) 0.30444(18) 0.91374(15) 0.0500(5) Uani d D 1 . .
    O O5 1.1435(3) 0.06759(16) 0.79342(17) 0.0490(4) Uani d D 1 . .
    C C1 1.5866(4) 0.5712(3) 0.9034(2) 0.0461(6) Uani d . 1 . .
    C C2 1.5618(5) 0.7069(3) 0.8999(3) 0.0553(7) Uani d . 1 . .
    H H2 1.6632 0.7576 0.9436 0.066 Uiso calc R 1 . .
    C C3 1.3954(5) 0.7612(3) 0.8350(3) 0.0567(7) Uani d . 1 . .
    H H3 1.3813 0.8493 0.8345 0.068 Uiso calc R 1 . .
    C C4 1.2374(5) 0.6858(2) 0.7657(2) 0.0476(6) Uani d . 1 . .
    C C5 1.0585(5) 0.7350(3) 0.6972(3) 0.0596(8) Uani d . 1 . .
    H H5A 1.0373 0.8226 0.6939 0.071 Uiso calc R 1 . .
    C C6 0.9124(5) 0.6572(3) 0.6344(3) 0.0610(8) Uani d . 1 . .
    H H6 0.7931 0.6918 0.5888 0.073 Uiso calc R 1 . .
    C C7 0.9433(5) 0.5268(3) 0.6391(2) 0.0513(7) Uani d . 1 . .
    C C8 1.1185(4) 0.4708(2) 0.7080(2) 0.0415(5) Uani d . 1 . .
    C C9 1.2625(4) 0.5534(2) 0.7693(2) 0.0400(5) Uani d . 1 . .
    C C10 0.6251(5) 0.4863(4) 0.5056(3) 0.0792(11) Uani d . 1 . .
    H H10A 0.5429 0.4153 0.4723 0.119 Uiso calc R 1 . .
    H H10B 0.6864 0.5372 0.4442 0.119 Uiso calc R 1 . .
    H H10C 0.5222 0.5367 0.5507 0.119 Uiso calc R 1 . .
    C C11 1.1382(4) 0.3280(2) 0.7160(2) 0.0419(5) Uani d . 1 . .
    H H11A 1.2906 0.3052 0.7459 0.050 Uiso calc R 1 . .
    H H11B 1.1181 0.2912 0.6387 0.050 Uiso calc R 1 . .
    C C12 0.9563(4) 0.2742(2) 0.79647(19) 0.0388(5) Uani d . 1 . .
    H H12 0.8090 0.3159 0.7777 0.047 Uiso calc R 1 . .
    C C13 0.9231(4) 0.1295(2) 0.7838(2) 0.0406(5) Uani d . 1 . .
    C C14 0.7685(5) 0.0804(3) 0.8780(3) 0.0628(8) Uani d . 1 . .
    H H14A 0.7520 -0.0100 0.8704 0.094 Uiso calc R 1 . .
    H H14B 0.6199 0.1200 0.8700 0.094 Uiso calc R 1 . .
    H H14C 0.8354 0.1002 0.9534 0.094 Uiso calc R 1 . .
    C C15 0.8225(5) 0.0987(3) 0.6642(3) 0.0628(8) Uani d . 1 . .
    H H15A 0.7866 0.0096 0.6600 0.094 Uiso calc R 1 . .
    H H15B 0.9324 0.1193 0.6059 0.094 Uiso calc R 1 . .
    H H15C 0.6846 0.1474 0.6505 0.094 Uiso calc R 1 . .
    H H4 0.935(6) 0.363(3) 0.937(4) 0.119(17) Uiso d D 1 . .
    H H5 1.183(6) 0.068(4) 0.8650(12) 0.089(12) Uiso d D 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 0.0453(9) 0.0336(9) 0.0515(10) 0.0040(7) -0.0063(7) -0.0039(7)
    O2 0.0526(10) 0.0556(12) 0.0683(12) 0.0103(9) -0.0159(9) -0.0154(10)
    O3 0.0719(13) 0.0715(15) 0.0581(12) -0.0035(11) -0.0275(10) 0.0085(11)
    O4 0.0630(11) 0.0466(11) 0.0400(9) 0.0096(9) -0.0081(8) -0.0065(8)
    O5 0.0460(9) 0.0389(10) 0.0616(12) 0.0071(7) -0.0058(8) -0.0042(9)
    C1 0.0428(12) 0.0441(15) 0.0512(14) 0.0015(11) -0.0013(11) -0.0098(12)
    C2 0.0581(15) 0.0403(15) 0.0676(18) -0.0087(12) -0.0002(14) -0.0088(13)
    C3 0.0722(17) 0.0299(13) 0.0683(18) -0.0035(13) 0.0078(15) -0.0034(12)
    C4 0.0567(14) 0.0356(14) 0.0508(15) 0.0018(12) 0.0047(12) 0.0054(12)
    C5 0.0716(18) 0.0427(16) 0.0645(18) 0.0122(14) 0.0013(15) 0.0140(14)
    C6 0.0656(17) 0.0572(19) 0.0599(17) 0.0137(14) -0.0073(14) 0.0186(15)
    C7 0.0573(15) 0.0544(17) 0.0416(14) 0.0014(13) -0.0065(12) 0.0098(13)
    C8 0.0475(12) 0.0371(12) 0.0398(13) 0.0011(10) -0.0002(10) 0.0037(10)
    C9 0.0450(12) 0.0345(13) 0.0406(13) 0.0035(10) 0.0023(10) 0.0042(10)
    C10 0.0586(16) 0.114(3) 0.0636(19) 0.001(2) -0.0203(15) 0.016(2)
    C11 0.0447(12) 0.0353(12) 0.0455(13) -0.0001(10) -0.0016(10) -0.0042(11)
    C12 0.0402(10) 0.0373(12) 0.0384(12) 0.0051(10) -0.0072(9) -0.0023(10)
    C13 0.0373(10) 0.0343(12) 0.0499(13) -0.0004(10) -0.0055(9) -0.0011(11)
    C14 0.0524(15) 0.0546(17) 0.082(2) -0.0116(13) 0.0071(14) 0.0101(16)
    C15 0.0668(17) 0.0530(17) 0.0672(18) -0.0063(14) -0.0239(14) -0.0130(15)
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 C1 . 1.369(3) ?
    O1 C9 . 1.373(3) ?
    O2 C1 . 1.209(3) ?
    O3 C7 . 1.361(3) ?
    O3 C10 . 1.430(3) ?
    O4 C12 . 1.421(3) ?
    O4 H4 . 0.840(10) ?
    O5 C13 . 1.437(3) ?
    O5 H5 . 0.846(10) ?
    C1 C2 . 1.434(4) ?
    C2 C3 . 1.332(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.434(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.384(4) ?
    C4 C9 . 1.401(3) ?
    C5 C6 . 1.369(4) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.383(4) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.400(3) ?
    C8 C9 . 1.383(3) ?
    C8 C11 . 1.509(3) ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 C12 . 1.529(3) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 C13 . 1.540(3) ?
    C12 H12 . 0.9800 ?
    C13 C15 . 1.510(4) ?
    C13 C14 . 1.512(4) ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    C15 H15A . 0.9600 ?
    C15 H15B . 0.9600 ?
    C15 H15C . 0.9600 ?
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
    C1 O1 C9 . . 122.44(19) ?
    C7 O3 C10 . . 118.9(3) ?
    C12 O4 H4 . . 109(3) ?
    C13 O5 H5 . . 107(3) ?
    O2 C1 O1 . . 116.4(2) ?
    O2 C1 C2 . . 125.8(3) ?
    O1 C1 C2 . . 117.9(2) ?
    C3 C2 C1 . . 120.8(3) ?
    C3 C2 H2 . . 119.6 ?
    C1 C2 H2 . . 119.6 ?
    C2 C3 C4 . . 121.0(2) ?
    C2 C3 H3 . . 119.5 ?
    C4 C3 H3 . . 119.5 ?
    C5 C4 C9 . . 117.6(3) ?
    C5 C4 C3 . . 124.4(3) ?
    C9 C4 C3 . . 118.0(2) ?
    C6 C5 C4 . . 121.3(3) ?
    C6 C5 H5A . . 119.3 ?
    C4 C5 H5A . . 119.3 ?
    C5 C6 C7 . . 119.6(3) ?
    C5 C6 H6 . . 120.2 ?
    C7 C6 H6 . . 120.2 ?
    O3 C7 C6 . . 124.5(2) ?
    O3 C7 C8 . . 113.5(2) ?
    C6 C7 C8 . . 122.0(3) ?
    C9 C8 C7 . . 116.2(2) ?
    C9 C8 C11 . . 123.4(2) ?
    C7 C8 C11 . . 120.4(2) ?
    O1 C9 C8 . . 116.90(19) ?
    O1 C9 C4 . . 119.8(2) ?
    C8 C9 C4 . . 123.3(2) ?
    O3 C10 H10A . . 109.5 ?
    O3 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    O3 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C8 C11 C12 . . 110.6(2) ?
    C8 C11 H11A . . 109.5 ?
    C12 C11 H11A . . 109.5 ?
    C8 C11 H11B . . 109.5 ?
    C12 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 108.1 ?
    O4 C12 C11 . . 108.45(18) ?
    O4 C12 C13 . . 109.84(19) ?
    C11 C12 C13 . . 113.30(19) ?
    O4 C12 H12 . . 108.4 ?
    C11 C12 H12 . . 108.4 ?
    C13 C12 H12 . . 108.4 ?
    O5 C13 C15 . . 107.1(2) ?
    O5 C13 C14 . . 109.6(2) ?
    C15 C13 C14 . . 110.5(2) ?
    O5 C13 C12 . . 109.36(17) ?
    C15 C13 C12 . . 110.0(2) ?
    C14 C13 C12 . . 110.2(2) ?
    C13 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C13 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C13 C15 H15A . . 109.5 ?
    C13 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C13 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
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
    C9 O1 C1 O2 . . . . 176.4(2) ?
    C9 O1 C1 C2 . . . . -3.2(4) ?
    O2 C1 C2 C3 . . . . -177.7(3) ?
    O1 C1 C2 C3 . . . . 1.9(4) ?
    C1 C2 C3 C4 . . . . -0.6(5) ?
    C2 C3 C4 C5 . . . . 179.2(3) ?
    C2 C3 C4 C9 . . . . 0.5(4) ?
    C9 C4 C5 C6 . . . . -0.6(4) ?
    C3 C4 C5 C6 . . . . -179.2(3) ?
    C4 C5 C6 C7 . . . . 0.0(5) ?
    C10 O3 C7 C6 . . . . 0.6(4) ?
    C10 O3 C7 C8 . . . . -179.7(2) ?
    C5 C6 C7 O3 . . . . -179.4(3) ?
    C5 C6 C7 C8 . . . . 1.0(5) ?
    O3 C7 C8 C9 . . . . 179.0(2) ?
    C6 C7 C8 C9 . . . . -1.3(4) ?
    O3 C7 C8 C11 . . . . -3.1(4) ?
    C6 C7 C8 C11 . . . . 176.6(3) ?
    C1 O1 C9 C8 . . . . -177.4(2) ?
    C1 O1 C9 C4 . . . . 3.2(3) ?
    C7 C8 C9 O1 . . . . -178.6(2) ?
    C11 C8 C9 O1 . . . . 3.6(3) ?
    C7 C8 C9 C4 . . . . 0.8(4) ?
    C11 C8 C9 C4 . . . . -177.1(3) ?
    C5 C4 C9 O1 . . . . 179.5(2) ?
    C3 C4 C9 O1 . . . . -1.8(4) ?
    C5 C4 C9 C8 . . . . 0.1(4) ?
    C3 C4 C9 C8 . . . . 178.9(2) ?
    C9 C8 C11 C12 . . . . 101.1(3) ?
    C7 C8 C11 C12 . . . . -76.7(3) ?
    C8 C11 C12 O4 . . . . -73.0(2) ?
    C8 C11 C12 C13 . . . . 164.76(19) ?
    O4 C12 C13 O5 . . . . -70.5(2) ?
    C11 C12 C13 O5 . . . . 51.0(2) ?
    O4 C12 C13 C15 . . . . 172.2(2) ?
    C11 C12 C13 C15 . . . . -66.4(3) ?
    O4 C12 C13 C14 . . . . 50.0(2) ?
    C11 C12 C13 C14 . . . . 171.5(2) ?
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
    O4 H4 O2 1_455 0.840(10)
                           2.010(10)
                                   2.842(3) 169(5) yes
    O5 H5 O2 2_847 0.850(10)
                           2.12(2) 2.936(3) 163(4) yes