#------------------------------------------------------------------------------
#$Date: 2016-02-20 17:35:30 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/04/2210462.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2210462
loop_
_publ_author_name
'dRuyck, Jérôme de'
'Preat, Julien'
'Perpète, Eric A.'
'Jacquemin, Denis'
'Wouters, Johan'
_publ_section_title
;
 2,6-Dihydroxyanthraquinone: an isomer of the well known alizarin dye
;
_journal_coeditor_code           AT2091
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4503
_journal_page_last               o4505
_journal_paper_doi               10.1107/S1600536806036828
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H8 O4'
_chemical_formula_moiety         'C14 H8 O4'
_chemical_formula_sum            'C14 H8 O4'
_chemical_formula_weight         240.20
_chemical_name_common            'Anthraflavic acid'
_chemical_name_systematic        2,6-dihydroxyanthraquinone
_space_group_IT_number           140
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4 2c'
_symmetry_space_group_name_H-M   'I 4/m c m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.640(4)
_cell_length_b                   13.640(4)
_cell_length_c                   6.678(3)
_cell_measurement_reflns_used    18
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.9
_cell_measurement_theta_min      19.7
_cell_volume                     1242.4(8)
_computing_cell_refinement       CAD-4/MACH3
_computing_data_collection       'CAD-4/MACH3 (Nonius, 2000)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  Nonius
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0085
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            702
_diffrn_reflns_theta_full        74.96
_diffrn_reflns_theta_max         74.96
_diffrn_reflns_theta_min         4.58
_diffrn_standards_decay_%        11.0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  0.8896
_exptl_absorpt_correction_T_min  0.6910
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(Alcock, 1970)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin needles'
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     35
_refine_ls_number_reflns         375
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1314P)²+0.1721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1845
_refine_ls_wR_factor_ref         0.1881
_reflns_number_gt                346
_reflns_number_total             375
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2091.cif
_cod_data_source_block           I
_cod_database_code               2210462
_cod_database_fobs_code          2210462
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x, z'
'-x, -y, z'
'y, -x, z'
'x, -y, -z+1/2'
'y, x, -z+1/2'
'-x, y, -z+1/2'
'-y, -x, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'x+1/2, -y+1/2, -z+1'
'y+1/2, x+1/2, -z+1'
'-x+1/2, y+1/2, -z+1'
'-y+1/2, -x+1/2, -z+1'
'-x, -y, -z'
'y, -x, -z'
'x, y, -z'
'-y, x, -z'
'-x, y, z-1/2'
'-y, -x, z-1/2'
'x, -y, z-1/2'
'y, x, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'-x+1/2, y+1/2, z'
'-y+1/2, -x+1/2, z'
'x+1/2, -y+1/2, z'
'y+1/2, x+1/2, z'
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 0.36072(9) -0.13928(9) 0.0000 0.0518(7) Uani d SU 1 . .
C C1 0.42437(12) -0.07563(12) 0.0000 0.0368(7) Uani d SU 1 . .
C C2 0.39765(11) 0.02914(11) 0.0000 0.0363(7) Uani d SU 1 . .
C C3 0.29948(14) 0.05674(13) 0.0000 0.0452(7) Uani d SDU 1 A .
H H3 0.2510 0.0088 0.0000 0.054 Uiso calc SR 1 . .
C C4 0.27310(13) 0.15455(14) 0.0000 0.0491(7) Uani d SDU 1 . .
O O4 0.1729(2) 0.1675(2) 0.0000 0.0692(10) Uani d SPU 0.50 A 1
H H4 0.1603 0.2263 0.0000 0.104 Uiso calc SPR 0.50 A 1
H H4' 0.2068(6) 0.170(2) 0.0000 0.083 Uiso d SPD 0.50 B 2
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 0.0387(9) 0.0387(9) 0.0781(14) -0.0073(6) 0.000 0.000
C1 0.0341(9) 0.0341(9) 0.0420(12) -0.0023(8) 0.000 0.000
C2 0.0321(10) 0.0337(10) 0.0430(10) 0.0001(7) 0.000 0.000
C3 0.0333(10) 0.0437(10) 0.0585(12) 0.0008(6) 0.000 0.000
C4 0.0372(10) 0.0464(11) 0.0638(13) 0.0093(7) 0.000 0.000
O4 0.0399(16) 0.0483(17) 0.119(2) 0.0096(11) 0.000 0.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O1 C1 C2 . 14_544 120.69(11)
O1 C1 C2 . . 120.69(11)
C2 C1 C2 14_544 . 118.6(2)
C3 C2 C2 . 30 119.29(10)
C3 C2 C1 . . 120.02(17)
C2 C2 C1 30 . 120.69(11)
C4 C3 C2 . . 120.80(17)
C4 C3 H3 . . 119.6
C2 C3 H3 . . 119.6
O4 C4 C3 . . 112.5(2)
O4 C4 C4 . 30 127.64(15)
C3 C4 C4 . 30 119.91(11)
C3 C4 H4' . . 118.6(19)
C4 C4 H4' 30 . 121.5(19)
C4 O4 H4 . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.228(3)
C1 C2 14_544 1.475(2)
C1 C2 . 1.475(2)
C2 C3 . 1.391(2)
C2 C2 30 1.412(3)
C3 C4 . 1.382(2)
C3 H3 . 0.9300
C4 O4 . 1.377(4)
C4 C4 30 1.396(4)
C4 H4' . 0.9300(10)
O4 H4 . 0.8200
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O4 H4 O1 0.82 1.86 2.68 178 yes
