##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_date_recd_electronic     2008-02-25
_journal_date_accepted     2008-06-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      7
_journal_page_first     o1305
_journal_page_last     o1305
_journal_paper_category     QO
_journal_coeditor_code     FB2091
_publ_contact_author_name     'Alex Saez'
_publ_contact_author_address
;
Instituto de Química
Química de Plantas Colombianas
Universidad de Antioquia
A.A. 1226
Medellín, Colombia
Grupo de procesos Ambientales y Biotecnologicos Departamento de Ingenieria de
Procesos Universidad EAFIT
A.A: 3300,
Medellín, Colombia
;
_publ_contact_author_email     asaez@eafit.edu.co
_publ_contact_author_fax     '0057 4 266 4284'
_publ_contact_author_phone     '0057 4 261 9500'
_publ_section_title
;
Semisynthetic roxburghin tetramethyl ether
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Saez, Alex' .
;
Instituto de Química
Química de Plantas Colombianas
Universidad de Antioquia
AA 1226
Medellín, Colombia
and
Grupo de Procesos Ambientales y Biotecnológicos
Departamento de Ingeniería de Procesos
Universidad EAFIT
AA 3300,
Medellín, Colombia
;
    'Ramirez de Arellano, Carmen' .
;
Departamento de Química Orgánica
Universidad de Valencia
E-46100 Valencia
Spain
;
    'El Aouad, Noureddine' .
;
Departamento de Farmacología
Facultad de Farmacia
Universidad de Valencia
Burjassot, Valencia
Spain
;
    'Rodriguez, Silvia' .
;
Instituto de Química
Química de Plantas Colombianas
Universidad de Antioquia
AA 1226
Medellín, Colombia
;
    'Otalvaro, Felipe' .
;
Instituto de Química
Química de Plantas Colombianas
Universidad de Antioquia
AA 1226
Medellín, Colombia
;
    'Cortes, Diego' .
;
Departamento de Farmacología
Facultad de Farmacia
Universidad de Valencia
Burjassot, Valencia
Spain
;
    'Saez, Jairo' .
;
Instituto de Química
Química de Plantas Colombianas
Universidad de Antioquia
AA 1226
Medellín, Colombia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(E)-2,3',4,5-tetramethoxystilbene
;
_chemical_name_common     'roxburghin tetramethyl ether'
_chemical_formula_moiety     'C18 H20 O4'
_chemical_formula_sum     'C18 H20 O4'
_chemical_formula_iupac     'C18 H20 O4'
_chemical_formula_weight     300.34
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.9633(4)
_cell_length_b     9.2454(5)
_cell_length_c     11.6194(5)
_cell_angle_alpha     73.400(2)
_cell_angle_beta     75.479(3)
_cell_angle_gamma     70.335(2)
_cell_volume     760.59(7)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     46078
_cell_measurement_theta_min     0.998
_cell_measurement_theta_max     30.034
_cell_measurement_temperature     150(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.311
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     320
_exptl_absorpt_coefficient_mu     0.092
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     150(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     'Nonius KappaCCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     9
_diffrn_reflns_number     8260
_diffrn_reflns_av_R_equivalents     0.0254
_diffrn_reflns_av_sigmaI/netI     0.0445
_diffrn_reflns_theta_min     2.69
_diffrn_reflns_theta_max     30.03
_diffrn_reflns_theta_full     30.03
_diffrn_measured_fraction_theta_max     0.988
_diffrn_measured_fraction_theta_full     0.988
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F\^2\^ against ALL reflections. The weighted
R-factor wR and goodness of fit S are based on
F\^2\^, conventional R-factors R are based on F,
with F set to zero for negative F\^2\^. The threshold expression
of F\^2\^ > σ(F\^2\^) is used only for calculating
R-factors(gt) etc. and is not relevant to the choice of
reflections for refinement. R-factors based on F\^2\^ are
statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total     4391
_reflns_number_gt     2785
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0820
_refine_ls_R_factor_gt     0.0472
_refine_ls_wR_factor_gt     0.1216
_refine_ls_wR_factor_ref     0.1360
_refine_ls_goodness_of_fit_ref     0.982
_refine_ls_restrained_S_all     0.982
_refine_ls_number_reflns     4391
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_number_constraints     76
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0789P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.292
_refine_diff_density_min     -0.231
_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 0.0016
                         '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'
_computing_data_collection     'COLLECT (Nonius, 1998)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 0.35419(11) 0.13391(9) 0.41479(8) 0.0342(2) Uani d . 1 . .
    O O2 0.16009(11) 0.25274(9) 0.59974(7) 0.0302(2) Uani d . 1 . .
    O O3 0.31164(11) 0.74440(9) 0.41175(7) 0.0322(2) Uani d . 1 . .
    O O4 0.83171(12) 1.06354(9) -0.08834(8) 0.0352(2) Uani d . 1 . .
    C C1 0.34968(15) 0.28542(12) 0.40914(10) 0.0257(2) Uani d . 1 . .
    C C2 0.24495(14) 0.34919(12) 0.50941(9) 0.0242(2) Uani d . 1 . .
    C C3 0.23241(14) 0.50121(12) 0.51169(10) 0.0252(2) Uani d . 1 . .
    H H3 0.1620 0.5441 0.5796 0.030 Uiso calc R 1 . .
    C C4 0.32276(14) 0.59219(12) 0.41457(10) 0.0242(2) Uani d . 1 . .
    C C5 0.42856(14) 0.53130(12) 0.31388(10) 0.0237(2) Uani d . 1 . .
    C C6 0.43875(15) 0.37648(12) 0.31392(10) 0.0260(2) Uani d . 1 . .
    H H6 0.5092 0.3330 0.2463 0.031 Uiso calc R 1 . .
    C C7 0.52275(15) 0.62808(13) 0.21313(10) 0.0255(2) Uani d . 1 . .
    H H7 0.5008 0.7340 0.2176 0.031 Uiso calc R 1 . .
    C C8 0.63618(15) 0.58230(13) 0.11577(10) 0.0286(2) Uani d . 1 . .
    H H8 0.6583 0.4762 0.1116 0.034 Uiso calc R 1 . .
    C C11 0.73066(15) 0.67918(13) 0.01411(10) 0.0266(2) Uani d . 1 . .
    C C12 0.72987(14) 0.83038(13) 0.01567(10) 0.0257(2) Uani d . 1 . .
    H H12 0.6661 0.8741 0.0844 0.031 Uiso calc R 1 . .
    C C13 0.82170(15) 0.91678(13) -0.08266(10) 0.0275(3) Uani d . 1 . .
    C C14 0.91383(17) 0.85479(15) -0.18482(11) 0.0352(3) Uani d . 1 . .
    H H14 0.9754 0.9144 -0.2524 0.042 Uiso calc R 1 . .
    C C15 0.91459(18) 0.70674(15) -0.18674(11) 0.0400(3) Uani d . 1 . .
    H H15 0.9770 0.6642 -0.2562 0.048 Uiso calc R 1 . .
    C C16 0.82497(17) 0.61818(14) -0.08813(11) 0.0348(3) Uani d . 1 . .
    H H16 0.8281 0.5154 -0.0906 0.042 Uiso calc R 1 . .
    C C17 0.48206(17) 0.05869(13) 0.32371(12) 0.0372(3) Uani d . 1 . .
    H H17A 0.4483 0.1127 0.2435 0.056 Uiso calc R 1 . .
    H H17B 0.4825 -0.0516 0.3411 0.056 Uiso calc R 1 . .
    H H17C 0.6030 0.0634 0.3241 0.056 Uiso calc R 1 . .
    C C18 0.06092(16) 0.31142(13) 0.70597(10) 0.0303(3) Uani d . 1 . .
    H H18A 0.1428 0.3348 0.7439 0.046 Uiso calc R 1 . .
    H H18B 0.0074 0.2319 0.7640 0.046 Uiso calc R 1 . .
    H H18C -0.0353 0.4077 0.6828 0.046 Uiso calc R 1 . .
    C C19 0.19201(16) 0.81424(13) 0.50742(11) 0.0329(3) Uani d . 1 . .
    H H19A 0.0689 0.8124 0.5097 0.049 Uiso calc R 1 . .
    H H19B 0.1939 0.9235 0.4930 0.049 Uiso calc R 1 . .
    H H19C 0.2309 0.7550 0.5854 0.049 Uiso calc R 1 . .
    C C20 0.75180(17) 1.12894(14) 0.01691(11) 0.0349(3) Uani d . 1 . .
    H H20A 0.6208 1.1449 0.0326 0.052 Uiso calc R 1 . .
    H H20B 0.7762 1.2302 0.0029 0.052 Uiso calc R 1 . .
    H H20C 0.8036 1.0566 0.0875 0.052 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
    O1 0.0446(5) 0.0235(4) 0.0337(5) -0.0156(3) 0.0077(4) -0.0104(3)
    O2 0.0344(4) 0.0262(4) 0.0267(4) -0.0133(3) 0.0047(3) -0.0040(3)
    O3 0.0395(5) 0.0247(4) 0.0317(4) -0.0148(3) 0.0080(4) -0.0108(3)
    O4 0.0432(5) 0.0296(4) 0.0328(5) -0.0187(4) 0.0041(4) -0.0064(4)
    C1 0.0290(6) 0.0202(5) 0.0279(6) -0.0089(4) -0.0023(5) -0.0054(4)
    C2 0.0240(5) 0.0245(5) 0.0221(5) -0.0092(4) -0.0019(4) -0.0015(4)
    C3 0.0251(5) 0.0255(5) 0.0243(5) -0.0078(4) -0.0008(4) -0.0066(4)
    C4 0.0256(5) 0.0212(5) 0.0264(6) -0.0083(4) -0.0024(4) -0.0062(4)
    C5 0.0231(5) 0.0239(5) 0.0242(5) -0.0089(4) -0.0024(4) -0.0040(4)
    C6 0.0278(6) 0.0255(5) 0.0244(5) -0.0095(4) 0.0002(4) -0.0069(4)
    C7 0.0272(6) 0.0238(5) 0.0255(6) -0.0097(4) -0.0024(5) -0.0045(4)
    C8 0.0339(6) 0.0233(5) 0.0279(6) -0.0116(4) 0.0006(5) -0.0056(4)
    C11 0.0261(5) 0.0276(6) 0.0244(5) -0.0091(4) -0.0007(4) -0.0046(4)
    C12 0.0259(5) 0.0282(5) 0.0217(5) -0.0089(4) 0.0002(4) -0.0059(4)
    C13 0.0274(6) 0.0281(6) 0.0266(6) -0.0105(5) -0.0020(5) -0.0048(5)
    C14 0.0397(7) 0.0398(7) 0.0259(6) -0.0210(6) 0.0055(5) -0.0051(5)
    C15 0.0488(8) 0.0436(7) 0.0278(6) -0.0192(6) 0.0094(6) -0.0149(6)
    C16 0.0434(7) 0.0302(6) 0.0309(6) -0.0158(5) 0.0058(5) -0.0112(5)
    C17 0.0439(7) 0.0279(6) 0.0381(7) -0.0126(5) 0.0071(6) -0.0141(5)
    C18 0.0343(6) 0.0345(6) 0.0211(5) -0.0152(5) 0.0019(5) -0.0038(5)
    C19 0.0353(6) 0.0276(6) 0.0358(7) -0.0111(5) 0.0055(5) -0.0142(5)
    C20 0.0374(7) 0.0310(6) 0.0373(7) -0.0134(5) 0.0003(5) -0.0104(5)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 . 1.3720(12) ?
    O1 C17 . 1.4298(13) ?
    O2 C2 . 1.3670(13) ?
    O2 C18 . 1.4308(13) ?
    O3 C4 . 1.3713(12) ?
    O3 C19 . 1.4231(13) ?
    O4 C13 . 1.3677(13) ?
    O4 C20 . 1.4281(13) ?
    C1 C6 . 1.3828(15) ?
    C1 C2 . 1.4052(14) ?
    C2 C3 . 1.3826(14) ?
    C3 C4 . 1.3988(15) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.3994(14) ?
    C5 C6 . 1.4060(14) ?
    C5 C7 . 1.4651(15) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.3336(16) ?
    C7 H7 . 0.9500 ?
    C8 C11 . 1.4721(15) ?
    C8 H8 . 0.9500 ?
    C11 C16 . 1.3942(15) ?
    C11 C12 . 1.4011(15) ?
    C12 C13 . 1.3896(15) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.3945(16) ?
    C14 C15 . 1.3733(16) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.3927(17) ?
    C15 H15 . 0.9500 ?
    C16 H16 . 0.9500 ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    C19 H19A . 0.9800 ?
    C19 H19B . 0.9800 ?
    C19 H19C . 0.9800 ?
    C20 H20A . 0.9800 ?
    C20 H20B . 0.9800 ?
    C20 H20C . 0.9800 ?
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 C17 . . 116.35(8) ?
    C2 O2 C18 . . 117.08(8) ?
    C4 O3 C19 . . 117.81(8) ?
    C13 O4 C20 . . 117.84(8) ?
    O1 C1 C6 . . 125.08(10) ?
    O1 C1 C2 . . 115.75(9) ?
    C6 C1 C2 . . 119.18(9) ?
    O2 C2 C3 . . 124.25(10) ?
    O2 C2 C1 . . 115.93(9) ?
    C3 C2 C1 . . 119.82(9) ?
    C2 C3 C4 . . 120.40(10) ?
    C2 C3 H3 . . 119.8 ?
    C4 C3 H3 . . 119.8 ?
    O3 C4 C3 . . 122.49(9) ?
    O3 C4 C5 . . 116.58(9) ?
    C3 C4 C5 . . 120.93(9) ?
    C4 C5 C6 . . 117.45(9) ?
    C4 C5 C7 . . 120.20(9) ?
    C6 C5 C7 . . 122.35(10) ?
    C1 C6 C5 . . 122.22(10) ?
    C1 C6 H6 . . 118.9 ?
    C5 C6 H6 . . 118.9 ?
    C8 C7 C5 . . 126.52(10) ?
    C8 C7 H7 . . 116.7 ?
    C5 C7 H7 . . 116.7 ?
    C7 C8 C11 . . 126.74(10) ?
    C7 C8 H8 . . 116.6 ?
    C11 C8 H8 . . 116.6 ?
    C16 C11 C12 . . 118.51(10) ?
    C16 C11 C8 . . 118.73(10) ?
    C12 C11 C8 . . 122.76(10) ?
    C13 C12 C11 . . 120.45(10) ?
    C13 C12 H12 . . 119.8 ?
    C11 C12 H12 . . 119.8 ?
    O4 C13 C12 . . 124.63(10) ?
    O4 C13 C14 . . 115.01(9) ?
    C12 C13 C14 . . 120.36(10) ?
    C15 C14 C13 . . 119.33(10) ?
    C15 C14 H14 . . 120.3 ?
    C13 C14 H14 . . 120.3 ?
    C14 C15 C16 . . 120.85(11) ?
    C14 C15 H15 . . 119.6 ?
    C16 C15 H15 . . 119.6 ?
    C15 C16 C11 . . 120.49(10) ?
    C15 C16 H16 . . 119.8 ?
    C11 C16 H16 . . 119.8 ?
    O1 C17 H17A . . 109.5 ?
    O1 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    O1 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    O2 C18 H18A . . 109.5 ?
    O2 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    O2 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    O3 C19 H19A . . 109.5 ?
    O3 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    O3 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    O4 C20 H20A . . 109.5 ?
    O4 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    O4 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
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
    C7 H7 O3 . 0.95 2.39 2.7504(14) 102
    C17 H17B O3 1_545 0.98 2.52 3.4046(16) 150
    C18 H18B O4 1_446 0.98 2.46 3.4342(15) 172
    C19 H19B O1 1_565 0.98 2.51 3.4082(15) 152
    C17 H17A Cg2 2_665 0.98 2.91 3.7863(15) 149
    C18 H18C Cg1 2_566 0.98 2.67 3.5578(14) 151
