##############################################################################
###                                                                        ###
###        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.                                        #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
9,10-Dihydroxy-4,4-dimethyl-5,8-dihydroanthracen-1(4H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H16 O3'
_chemical_formula_sum     'C16 H16 O3'
_chemical_formula_iupac     'C16 H16 O3'
_chemical_formula_weight     256.29
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n m a'
_symmetry_space_group_name_Hall     '-P 2ac 2n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z'
    'x+1/2, -y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z'
    '-x-1/2, y-1/2, z-1/2'
_cell_length_a     8.5944(5)
_cell_length_b     7.6024(5)
_cell_length_c     19.2949(12)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1260.69(14)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2361
_cell_measurement_theta_min     2.594
_cell_measurement_theta_max     24.997
_cell_measurement_temperature     150(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.43
_exptl_crystal_size_mid     0.38
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.350
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     544
_exptl_absorpt_coefficient_mu     0.092
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS in SAINT-NT; Bruker, 1999)'
_exptl_absorpt_correction_T_min     0.9613
_exptl_absorpt_correction_T_max     0.9926
_exptl_special_details
;
10 s by frame separated by 0.3 °
;
_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     'Siemens SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7422
_diffrn_reflns_av_R_equivalents     0.0430
_diffrn_reflns_av_sigmaI/netI     0.0304
_diffrn_reflns_theta_min     2.11
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² 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     1198
_reflns_number_gt     948
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0529
_refine_ls_R_factor_gt     0.0439
_refine_ls_wR_factor_gt     0.1114
_refine_ls_wR_factor_ref     0.1177
_refine_ls_goodness_of_fit_ref     1.006
_refine_ls_restrained_S_all     1.006
_refine_ls_number_reflns     1198
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0796P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_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     0.332
_refine_diff_density_min     -0.293
_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     'SMART-NT (Bruker, 2001)'
_computing_cell_refinement     'SAINT-NT (Bruker, 1999)'
_computing_data_reduction     'SAINT-NT (Bruker, 1999)'
_computing_structure_solution     'SHELXTL-NT (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL-NT (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL-NT (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL-NT (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 1.23661(15) 0.2500 0.97450(7) 0.0430(4) Uani d S 1 . .
    C C1 1.1134(2) 0.2500 0.93987(9) 0.0316(5) Uani d S 1 . .
    C C2 1.1204(2) 0.2500 0.86508(10) 0.0394(5) Uani d S 1 . .
    H H2B 1.2188 0.2500 0.8427 0.047 Uiso calc SR 1 . .
    C C3 0.9915(2) 0.2500 0.82719(10) 0.0366(5) Uani d S 1 . .
    H H3A 1.0040 0.2500 0.7783 0.044 Uiso calc SR 1 . .
    C C4 0.8283(2) 0.2500 0.85428(9) 0.0276(5) Uani d S 1 . .
    C C11 0.74913(15) 0.41540(18) 0.82447(7) 0.0319(4) Uani d . 1 . .
    H H11A 0.7543 0.4123 0.7737 0.048 Uiso calc R 1 . .
    H H11B 0.8027 0.5206 0.8415 0.048 Uiso calc R 1 . .
    H H11C 0.6400 0.4184 0.8392 0.048 Uiso calc R 1 . .
    C C4A 0.8227(2) 0.2500 0.93365(10) 0.0250(4) Uani d S 1 . .
    C C10 0.68158(19) 0.2500 0.96919(10) 0.0257(5) Uani d S 1 . .
    O O3 0.54736(14) 0.2500 0.93053(6) 0.0349(4) Uani d S 1 . .
    H H3 0.4700 0.2500 0.9571 0.052 Uiso calc SR 1 . .
    C C10A 0.67531(19) 0.2500 1.04249(9) 0.0246(5) Uani d S 1 . .
    C C5 0.5186(2) 0.2500 1.07767(10) 0.0293(5) Uani d S 1 . .
    H H5A 0.4600 0.3551 1.0623 0.035 Uiso calc PR 0.50 . .
    H H5B 0.4600 0.1449 1.0623 0.035 Uiso calc PR 0.50 . .
    C C6 0.5260(2) 0.2500 1.15519(10) 0.0302(5) Uani d S 1 . .
    H H6A 0.4305 0.2500 1.1800 0.036 Uiso calc SR 1 . .
    C C7 0.6566(2) 0.2500 1.19124(10) 0.0299(5) Uani d S 1 . .
    H H7A 0.6495 0.2500 1.2404 0.036 Uiso calc SR 1 . .
    C C8 0.8143(2) 0.2500 1.15932(10) 0.0311(5) Uani d S 1 . .
    H H8A 0.8718 0.1448 1.1755 0.037 Uiso calc PR 0.50 . .
    H H8B 0.8718 0.3552 1.1755 0.037 Uiso calc PR 0.50 . .
    C C8A 0.8116(2) 0.2500 1.08099(9) 0.0252(4) Uani d S 1 . .
    C C9 0.9537(2) 0.2500 1.04619(9) 0.0257(5) Uani d S 1 . .
    O O2 1.08404(15) 0.2500 1.08586(6) 0.0356(4) Uani d S 1 . .
    H H2 1.1629 0.2500 1.0602 0.053 Uiso calc SR 1 . .
    C C9A 0.9614(2) 0.2500 0.97343(10) 0.0255(5) Uani d S 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 0.0199(7) 0.0740(12) 0.0351(8) 0.000 -0.0021(6) 0.000
    C1 0.0210(10) 0.0430(12) 0.0310(11) 0.000 -0.0009(8) 0.000
    C2 0.0246(10) 0.0629(14) 0.0306(12) 0.000 0.0075(9) 0.000
    C3 0.0322(11) 0.0527(13) 0.0248(10) 0.000 0.0037(8) 0.000
    C4 0.0232(9) 0.0384(12) 0.0213(10) 0.000 -0.0015(7) 0.000
    C11 0.0346(8) 0.0375(8) 0.0237(7) -0.0025(6) -0.0025(5) 0.0023(6)
    C4A 0.0230(10) 0.0287(10) 0.0232(10) 0.000 -0.0008(7) 0.000
    C10 0.0211(10) 0.0313(11) 0.0246(10) 0.000 -0.0020(7) 0.000
    O3 0.0189(7) 0.0610(10) 0.0247(7) 0.000 -0.0024(5) 0.000
    C10A 0.0243(10) 0.0264(10) 0.0233(10) 0.000 0.0004(7) 0.000
    C5 0.0226(10) 0.0377(11) 0.0276(11) 0.000 0.0003(7) 0.000
    C6 0.0286(10) 0.0335(11) 0.0286(10) 0.000 0.0069(8) 0.000
    C7 0.0354(11) 0.0323(11) 0.0221(10) 0.000 0.0021(8) 0.000
    C8 0.0291(10) 0.0395(12) 0.0247(10) 0.000 -0.0036(8) 0.000
    C8A 0.0262(10) 0.0261(10) 0.0233(10) 0.000 -0.0012(7) 0.000
    C9 0.0222(9) 0.0307(11) 0.0243(10) 0.000 -0.0039(7) 0.000
    O2 0.0215(7) 0.0583(9) 0.0271(8) 0.000 -0.0058(6) 0.000
    C9A 0.0225(10) 0.0291(10) 0.0248(10) 0.000 -0.0008(7) 0.000
_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 . 1.252(2) ?
    C1 C2 . 1.444(3) ?
    C1 C9A . 1.458(2) ?
    C2 C3 . 1.327(3) ?
    C2 H2B . 0.9500 ?
    C3 C4 . 1.497(2) ?
    C3 H3A . 0.9500 ?
    C4 C4A . 1.532(3) ?
    C4 C11 7_565 1.5410(16) ?
    C4 C11 . 1.5410(16) ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C4A C10 . 1.393(2) ?
    C4A C9A . 1.418(2) ?
    C10 O3 . 1.374(2) ?
    C10 C10A . 1.415(3) ?
    O3 H3 . 0.8400 ?
    C10A C8A . 1.387(2) ?
    C10A C5 . 1.508(2) ?
    C5 C6 . 1.497(3) ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C6 C7 . 1.320(3) ?
    C6 H6A . 0.9500 ?
    C7 C8 . 1.489(3) ?
    C7 H7A . 0.9500 ?
    C8 C8A . 1.512(3) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C8A C9 . 1.394(2) ?
    C9 O2 . 1.357(2) ?
    C9 C9A . 1.405(3) ?
    O2 H2 . 0.8400 ?
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
    O1 C1 C2 . . 119.87(16) ?
    O1 C1 C9A . . 121.38(17) ?
    C2 C1 C9A . . 118.75(16) ?
    C3 C2 C1 . . 121.05(17) ?
    C3 C2 H2B . . 119.5 ?
    C1 C2 H2B . . 119.5 ?
    C2 C3 C4 . . 126.13(18) ?
    C2 C3 H3A . . 116.9 ?
    C4 C3 H3A . . 116.9 ?
    C3 C4 C4A . . 112.24(15) ?
    C3 C4 C11 . 7_565 106.46(10) ?
    C4A C4 C11 . 7_565 111.05(10) ?
    C3 C4 C11 . . 106.46(10) ?
    C4A C4 C11 . . 111.05(10) ?
    C11 C4 C11 7_565 . 109.37(14) ?
    C4 C11 H11A . . 109.5 ?
    C4 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C4 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C10 C4A C9A . . 117.74(17) ?
    C10 C4A C4 . . 121.29(15) ?
    C9A C4A C4 . . 120.97(15) ?
    O3 C10 C4A . . 117.62(16) ?
    O3 C10 C10A . . 120.71(15) ?
    C4A C10 C10A . . 121.67(16) ?
    C10 O3 H3 . . 109.5 ?
    C8A C10A C10 . . 120.20(16) ?
    C8A C10A C5 . . 120.86(17) ?
    C10 C10A C5 . . 118.94(16) ?
    C6 C5 C10A . . 114.34(15) ?
    C6 C5 H5A . . 108.7 ?
    C10A C5 H5A . . 108.7 ?
    C6 C5 H5B . . 108.7 ?
    C10A C5 H5B . . 108.7 ?
    H5A C5 H5B . . 107.6 ?
    C7 C6 C5 . . 124.20(17) ?
    C7 C6 H6A . . 117.9 ?
    C5 C6 H6A . . 117.9 ?
    C6 C7 C8 . . 123.79(17) ?
    C6 C7 H7A . . 118.1 ?
    C8 C7 H7A . . 118.1 ?
    C7 C8 C8A . . 113.53(15) ?
    C7 C8 H8A . . 108.9 ?
    C8A C8 H8A . . 108.9 ?
    C7 C8 H8B . . 108.9 ?
    C8A C8 H8B . . 108.9 ?
    H8A C8 H8B . . 107.7 ?
    C10A C8A C9 . . 118.81(17) ?
    C10A C8A C8 . . 123.28(16) ?
    C9 C8A C8 . . 117.91(15) ?
    O2 C9 C8A . . 116.85(16) ?
    O2 C9 C9A . . 121.64(16) ?
    C8A C9 C9A . . 121.50(16) ?
    C9 O2 H2 . . 109.5 ?
    C9 C9A C4A . . 120.08(16) ?
    C9 C9A C1 . . 119.07(16) ?
    C4A C9A C1 . . 120.86(16) ?
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
    C2 C3 C4 C11 . . . . 121.70(9) ?
    C11 C4 C4A C10 . . . . 60.96(10) ?
    C11 C4 C4A C9A . . . . -119.04(10) ?
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
    O2 H2 O1 . 0.84 1.77 2.5172(18) 147.2
    O3 H3 O1 1_455 0.84 2.03 2.8022(18) 151.9
data_global
_journal_date_recd_electronic     2008-04-16
_journal_date_accepted     2008-04-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      7
_journal_page_first     o1316
_journal_page_last     o1316
_journal_paper_category     QO
_journal_coeditor_code     HG2395
_publ_contact_author_name     'Ramiro Araya-Maturana'
_publ_contact_author_address
;
Departamento de Química Orgánica
Facultad de Ciencias Químicas y Farmaceúticas
Universidad de Chile
Casilla 233
Santiago
Chile
;
_publ_contact_author_email     raraya@uchile.cl
_publ_contact_author_fax     '(56 2)9782874'
_publ_contact_author_phone     '(56 2)9782868'
_publ_section_title
;
9,10-Dihydroxy-4,4-dimethyl-5,8-dihydroanthracen-1(4H)-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Ramírez-Rodríguez, Oney' .
;
Departamento de Química Orgánica
Facultad de Ciencias Químicas y Farmaceúticas
Universidad de Chile
Casilla 233
Santiago
Chile
;
    'Martínez-Cifuentes, Maximiliano' .
;
Departamento de Química Orgánica
Facultad de Ciencias Químicas y Farmaceúticas
Universidad de Chile
Casilla 233
Santiago
Chile
;
    'Ibañez, Andres' .
;
Centro de Investigación Interdisciplinaria Avanzada
en Ciencia de los Materiales
CIMAT
Universidad de Chile
Santiago, Chile
;
    'Vega, Andrés' .
;
Laboratorio de Recursos Naturales
Departamento de Ciencias Químicas
Facultad de Ecología y Recursos Naturales
Universidad Andrés Bello
Av. República 275, Santiago, Chile
;
    'Araya-Maturana, Ramiro' .
;
Departamento de Química Orgánica
Facultad de Ciencias Químicas y Farmaceúticas
Universidad de Chile
Casilla 233
Santiago
Chile
;
