# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
L.Miranda
M.Mijangos
J.Gonzalez-Marrero
P.Vincent-Ruz
A.Lujan-Montelongo
D.Olivera-Diaz
E.Bautista
A.Ortega
M.d.l.L.Campos-Gonzalez
R.Gamez-Montano
_publ_contact_author_name        'Luis Miranda'
_publ_contact_author_email       lmiranda@servidor.unam.mx

data_068mgl10
_database_code_depnum_ccdc_archive 'CCDC 869563'
#TrackingRef '068MGL10.cif'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_absolute_configuration unk

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C20 H18 O5'

_chemical_formula_weight         338.34

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'

_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                   7.2980(15)

_cell_length_b                   13.566(3)

_cell_length_c                   17.045(3)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     1687.5(6)

_cell_formula_units_Z            4

_cell_measurement_temperature    298(2)

_cell_measurement_reflns_used    1870

_cell_measurement_theta_min      2.39

_cell_measurement_theta_max      23.61

_exptl_crystal_description       Prism

_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.30

_exptl_crystal_size_mid          0.09

_exptl_crystal_size_min          0.08

_exptl_crystal_density_meas      .

_exptl_crystal_density_diffrn    1.332

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             712

_exptl_absorpt_coefficient_mu    0.096

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9719

_exptl_absorpt_correction_T_max  0.9924

_exptl_absorpt_process_details   
;

sadabs, Sheldrick, G. M. (1996). University of Gottingen, Germany.

;

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      298(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX AXS CCD area detector'

_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 0.83

_diffrn_standards_number         .

_diffrn_standards_interval_count .

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        .

_diffrn_reflns_number            14051

_diffrn_reflns_av_R_equivalents  0.0799

_diffrn_reflns_av_sigmaI/netI    0.0693

_diffrn_reflns_limit_h_min       -8

_diffrn_reflns_limit_h_max       8

_diffrn_reflns_limit_k_min       -16

_diffrn_reflns_limit_k_max       16

_diffrn_reflns_limit_l_min       -20

_diffrn_reflns_limit_l_max       20

_diffrn_reflns_theta_min         1.92

_diffrn_reflns_theta_max         25.40

_reflns_number_total             3104

_reflns_number_gt                1812

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V 5.625 (Bruker, 1999)'

_computing_cell_refinement       'SMART V 5.625 (Bruker, 1999)'

_computing_data_reduction        'SAINT V 6.23A (Bruker, 1999)'

_computing_structure_solution    'SHELXTL V 6.12 (Sheldrick, 2000)'

_computing_structure_refinement  'SHELXTL V 6.12 (Sheldrick, 2000)'

_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'

_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'

_solved_by                       'Simon Hernandez-Ortega'

_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^ > 2sigma(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.

;

_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0438P)^2^] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881, 1303 Friedel pairs merged'

_refine_ls_abs_structure_Flack   1.5(17)

_refine_ls_number_reflns         3104

_refine_ls_number_parameters     228

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.1069

_refine_ls_R_factor_gt           0.0510

_refine_ls_wR_factor_ref         0.1156

_refine_ls_wR_factor_gt          0.0969

_refine_ls_goodness_of_fit_ref   1.000

_refine_ls_restrained_S_all      1.000

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000

loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group

O1 O 0.9720(3) 0.25171(14) 0.10708(12) 0.0505(6) Uani 1 1 d . . .
O2 O 0.8214(4) -0.03060(16) 0.15064(15) 0.0746(8) Uani 1 1 d . . .
O3 O 1.1169(4) -0.02854(17) -0.02637(17) 0.0835(9) Uani 1 1 d . . .
O4 O 0.8902(3) -0.13534(15) -0.04337(14) 0.0637(7) Uani 1 1 d . . .
O5 O 0.9427(4) 0.39328(17) -0.24122(14) 0.0766(8) Uani 1 1 d . . .
C2 C 0.9215(4) 0.1905(2) 0.04661(19) 0.0450(9) Uani 1 1 d . . .
C3 C 0.8703(5) 0.0960(2) 0.05910(18) 0.0468(9) Uani 1 1 d . . .
C4 C 0.8671(5) 0.0554(2) 0.1382(2) 0.0524(9) Uani 1 1 d . . .
C5 C 0.9278(5) 0.0930(3) 0.2795(2) 0.0628(10) Uani 1 1 d . . .
H5 H 0.8919 0.0295 0.2933 0.075 Uiso 1 1 calc R . .
C6 C 0.9846(6) 0.1569(3) 0.3362(2) 0.0708(11) Uani 1 1 d . . .
H6 H 0.9883 0.1367 0.3883 0.085 Uiso 1 1 calc R . .
C7 C 1.0369(6) 0.2521(3) 0.3165(2) 0.0664(11) Uani 1 1 d . . .
H7 H 1.0770 0.2949 0.3554 0.080 Uiso 1 1 calc R . .
C8 C 1.0301(5) 0.2834(2) 0.2404(2) 0.0579(10) Uani 1 1 d . . .
H8 H 1.0629 0.3475 0.2272 0.069 Uiso 1 1 calc R . .
C9 C 0.9732(5) 0.2173(2) 0.18308(19) 0.0480(9) Uani 1 1 d . . .
C10 C 0.9231(5) 0.1219(2) 0.2011(2) 0.0515(9) Uani 1 1 d . . .
C11 C 0.9312(4) 0.2451(2) -0.02847(19) 0.0455(8) Uani 1 1 d . . .
C12 C 0.9923(5) 0.2016(2) -0.0975(2) 0.0523(9) Uani 1 1 d . . .
H12 H 1.0311 0.1363 -0.0967 0.063 Uiso 1 1 calc R . .
C13 C 0.9965(5) 0.2529(2) -0.1668(2) 0.0585(9) Uani 1 1 d . . .
H13 H 1.0388 0.2225 -0.2122 0.070 Uiso 1 1 calc R . .
C14 C 0.9378(5) 0.3502(2) -0.1691(2) 0.0537(9) Uani 1 1 d . . .
C15 C 0.8813(5) 0.3958(2) -0.1013(2) 0.0527(9) Uani 1 1 d . . .
H15 H 0.8449 0.4615 -0.1022 0.063 Uiso 1 1 calc R . .
C16 C 0.8787(4) 0.3435(2) -0.0316(2) 0.0487(8) Uani 1 1 d . . .
H16 H 0.8410 0.3749 0.0141 0.058 Uiso 1 1 calc R . .
C17 C 0.8081(5) 0.0262(2) -0.00361(19) 0.0516(9) Uani 1 1 d . . .
H17A H 0.7746 0.0632 -0.0501 0.062 Uiso 1 1 calc R . .
H17B H 0.7004 -0.0091 0.0144 0.062 Uiso 1 1 calc R . .
C18 C 0.9578(5) -0.0472(2) -0.02413(19) 0.0522(9) Uani 1 1 d . . .
C19 C 1.0249(6) -0.2073(2) -0.0701(2) 0.0795(13) Uani 1 1 d . . .
H19A H 1.0861 -0.1827 -0.1166 0.095 Uiso 1 1 calc R . .
H19B H 1.1166 -0.2171 -0.0296 0.095 Uiso 1 1 calc R . .
C20 C 0.9377(6) -0.2998(3) -0.0877(3) 0.0996(16) Uani 1 1 d . . .
H20A H 0.8483 -0.2903 -0.1283 0.149 Uiso 1 1 calc R . .
H20B H 0.8783 -0.3246 -0.0414 0.149 Uiso 1 1 calc R . .
H20C H 1.0281 -0.3463 -0.1051 0.149 Uiso 1 1 calc R . .
C21 C 0.8967(6) 0.4956(3) -0.2467(2) 0.0874(14) Uani 1 1 d . . .
H21A H 0.9843 0.5338 -0.2176 0.131 Uiso 1 1 calc R . .
H21B H 0.7765 0.5061 -0.2254 0.131 Uiso 1 1 calc R . .
H21C H 0.8986 0.5156 -0.3007 0.131 Uiso 1 1 calc R . .

loop_

_atom_site_aniso_label

_atom_site_aniso_U_11

_atom_site_aniso_U_22

_atom_site_aniso_U_33

_atom_site_aniso_U_23

_atom_site_aniso_U_13

_atom_site_aniso_U_12

O1 0.0548(15) 0.0379(11) 0.0589(14) -0.0043(12) -0.0010(12) -0.0017(12)
O2 0.106(2) 0.0357(14) 0.0821(18) 0.0035(13) -0.0073(16) -0.0115(14)
O3 0.0484(16) 0.0566(15) 0.145(3) -0.0284(17) -0.0023(19) -0.0035(14)
O4 0.0606(16) 0.0414(12) 0.0892(18) -0.0205(13) 0.0093(15) -0.0016(12)
O5 0.108(2) 0.0602(16) 0.0620(16) 0.0080(13) -0.0037(16) 0.0001(16)
C2 0.042(2) 0.0354(18) 0.057(2) -0.0124(17) -0.0023(18) 0.0040(15)
C3 0.047(2) 0.0349(18) 0.059(2) -0.0086(17) 0.0002(17) 0.0059(17)
C4 0.056(2) 0.0353(19) 0.066(2) -0.0027(18) -0.0002(19) 0.0009(19)
C5 0.075(3) 0.052(2) 0.062(2) 0.002(2) 0.007(2) 0.001(2)
C6 0.086(3) 0.070(3) 0.057(2) -0.001(2) 0.005(2) -0.006(2)
C7 0.073(3) 0.068(3) 0.058(2) -0.015(2) 0.000(2) -0.002(2)
C8 0.065(3) 0.046(2) 0.063(2) -0.0084(19) -0.002(2) -0.0049(19)
C9 0.047(2) 0.0408(19) 0.056(2) 0.0016(17) 0.0066(18) 0.0014(17)
C10 0.054(2) 0.042(2) 0.058(2) -0.0037(17) 0.0040(18) 0.0075(18)
C11 0.041(2) 0.0364(17) 0.059(2) -0.0030(17) -0.0048(18) 0.0009(16)
C12 0.053(2) 0.0416(18) 0.062(2) -0.0060(18) 0.001(2) 0.0054(18)
C13 0.069(3) 0.053(2) 0.054(2) -0.0052(19) 0.003(2) 0.002(2)
C14 0.056(2) 0.050(2) 0.055(2) 0.004(2) -0.002(2) -0.0066(19)
C15 0.052(2) 0.0405(18) 0.066(2) 0.001(2) -0.002(2) 0.0009(18)
C16 0.047(2) 0.0432(19) 0.056(2) -0.0081(18) 0.0000(19) -0.0022(17)
C17 0.050(2) 0.0420(19) 0.063(2) -0.0073(18) -0.0026(18) -0.0030(18)
C18 0.057(2) 0.043(2) 0.057(2) -0.0071(17) -0.002(2) -0.0025(19)
C19 0.075(3) 0.052(2) 0.111(3) -0.027(2) 0.008(3) 0.007(2)
C20 0.097(4) 0.058(2) 0.144(4) -0.021(3) 0.023(3) 0.015(3)
C21 0.120(4) 0.061(3) 0.082(3) 0.019(2) -0.009(3) -0.004(3)

_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell esds are taken

into account individually in the estimation of esds in distances, angles

and torsion angles; correlations between esds in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell esds is used for estimating esds involving l.s. planes.

;

loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag

O1 C2 1.374(3) . ?
O1 C9 1.377(4) . ?
O2 C4 1.232(3) . ?
O3 C18 1.189(4) . ?
O4 C18 1.334(4) . ?
O4 C19 1.458(4) . ?
O5 C14 1.361(4) . ?
O5 C21 1.431(4) . ?
C2 C3 1.352(4) . ?
C2 C11 1.480(4) . ?
C3 C4 1.457(4) . ?
C3 C17 1.499(4) . ?
C4 C10 1.459(4) . ?
C5 C6 1.363(5) . ?
C5 C10 1.394(4) . ?
C6 C7 1.388(5) . ?
C7 C8 1.365(5) . ?
C8 C9 1.390(4) . ?
C9 C10 1.379(4) . ?
C11 C16 1.390(4) . ?
C11 C12 1.390(4) . ?
C12 C13 1.371(4) . ?
C13 C14 1.388(4) . ?
C14 C15 1.375(4) . ?
C15 C16 1.383(4) . ?
C17 C18 1.519(4) . ?
C19 C20 1.439(5) . ?

loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag

C2 O1 C9 120.2(2) . . ?
C18 O4 C19 115.3(3) . . ?
C14 O5 C21 118.0(3) . . ?
C3 C2 O1 121.9(3) . . ?
C3 C2 C11 128.6(3) . . ?
O1 C2 C11 109.5(2) . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 C17 124.8(3) . . ?
C4 C3 C17 114.6(3) . . ?
O2 C4 C3 121.4(3) . . ?
O2 C4 C10 122.4(3) . . ?
C3 C4 C10 116.2(3) . . ?
C6 C5 C10 120.5(3) . . ?
C5 C6 C7 120.2(4) . . ?
C8 C7 C6 120.7(3) . . ?
C7 C8 C9 118.5(3) . . ?
O1 C9 C10 121.7(3) . . ?
O1 C9 C8 116.4(3) . . ?
C10 C9 C8 121.9(3) . . ?
C9 C10 C5 118.1(3) . . ?
C9 C10 C4 119.4(3) . . ?
C5 C10 C4 122.5(3) . . ?
C16 C11 C12 117.6(3) . . ?
C16 C11 C2 120.1(3) . . ?
C12 C11 C2 122.3(3) . . ?
C13 C12 C11 121.4(3) . . ?
C12 C13 C14 120.1(3) . . ?
O5 C14 C15 125.0(3) . . ?
O5 C14 C13 115.3(3) . . ?
C15 C14 C13 119.7(3) . . ?
C14 C15 C16 119.7(3) . . ?
C15 C16 C11 121.5(3) . . ?
C3 C17 C18 111.1(3) . . ?
O3 C18 O4 122.9(3) . . ?
O3 C18 C17 124.8(3) . . ?
O4 C18 C17 112.2(3) . . ?
C20 C19 O4 110.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        25.40

_diffrn_measured_fraction_theta_full 0.997

_refine_diff_density_max         0.132

_refine_diff_density_min         -0.127

_refine_diff_density_rms         0.031