#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/71/2207186.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_2207186
loop_
_publ_author_name
'Shea-Lin Ng'
'Ibrahim Abdul Razak'
'Hoong-Kun Fun'
'Sompong Boonsri'
'Suchada Chantrapromma'
'Uma Prawat'
_publ_section_title
;
 1,3-Dihydroxy-2-methyl-9,10-anthraquinone
;
_journal_coeditor_code           CI6670
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3656
_journal_page_last               o3658
_journal_paper_doi               10.1107/S1600536805031697
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C15 H10 O4'
_chemical_formula_moiety         'C15 H10 O4'
_chemical_formula_sum            'C15 H10 O4'
_chemical_formula_weight         254.23
_chemical_melting_point          .442E-305
_chemical_name_systematic
;
1,3-dihydroxy-2-methylanthra-9,10-quinone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 97.6100(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.35170(10)
_cell_length_b                   7.32680(10)
_cell_length_c                   21.1186(4)
_cell_measurement_reflns_used    4302
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      1.95
_cell_volume                     1127.52(3)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11402
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_correction_T_min  0.8283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            light_brown
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0833P)²+0.1198P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1477
_reflns_number_gt                2066
_reflns_number_total             2798
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6670.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207186
_cod_database_fobs_code          2207186
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_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_type_symbol
O1 0.76480(12) 0.16468(16) 0.43117(5) 0.0568(3) Uani d . 1 O
O2 0.56385(13) 0.26507(17) 0.32832(5) 0.0603(3) Uani d . 1 O
H2A 0.6560 0.2265 0.3504 0.091 Uiso calc R 1 H
O3 -0.03121(12) 0.47491(16) 0.34194(5) 0.0551(3) Uani d . 1 O
H3A -0.0948 0.5129 0.3682 0.083 Uiso calc R 1 H
O4 0.23316(13) 0.35636(15) 0.57119(5) 0.0533(3) Uani d . 1 O
C1 0.7214(2) 0.1308(2) 0.66453(8) 0.0603(4) Uani d . 1 C
H1 0.7401 0.1132 0.7085 0.072 Uiso calc R 1 H
C2 0.8569(2) 0.0845(2) 0.62807(8) 0.0590(4) Uani d . 1 C
H2 0.9669 0.0355 0.6477 0.071 Uiso calc R 1 H
C3 0.83088(18) 0.11025(18) 0.56294(8) 0.0498(3) Uani d . 1 C
H3 0.9237 0.0800 0.5389 0.060 Uiso calc R 1 H
C4 0.66581(16) 0.18143(16) 0.53298(6) 0.0393(3) Uani d . 1 C
C5 0.63997(15) 0.20675(16) 0.46262(6) 0.0403(3) Uani d . 1 C
C6 0.46581(15) 0.27964(16) 0.43235(6) 0.0368(3) Uani d . 1 C
C7 0.43381(17) 0.30360(18) 0.36586(6) 0.0425(3) Uani d . 1 C
C8 0.26579(18) 0.37000(19) 0.33495(6) 0.0449(3) Uani d . 1 C
C9 0.13032(16) 0.41185(17) 0.37266(6) 0.0411(3) Uani d . 1 C
C10 0.15826(15) 0.38997(16) 0.43874(6) 0.0381(3) Uani d . 1 C
H10 0.0650 0.4188 0.4628 0.046 Uiso calc R 1 H
C11 0.32405(15) 0.32561(15) 0.46859(6) 0.0347(3) Uani d . 1 C
C12 0.35158(16) 0.30696(16) 0.53917(6) 0.0378(3) Uani d . 1 C
C13 0.52759(16) 0.22863(16) 0.56968(6) 0.0392(3) Uani d . 1 C
C14 0.5570(2) 0.2039(2) 0.63538(7) 0.0516(4) Uani d . 1 C
H14 0.4662 0.2364 0.6600 0.062 Uiso calc R 1 H
C15 0.2356(2) 0.3961(3) 0.26395(7) 0.0698(5) Uani d . 1 C
H15A 0.1428 0.4872 0.2531 0.105 Uiso calc R 1 H
H15B 0.1966 0.2829 0.2436 0.105 Uiso calc R 1 H
H15C 0.3480 0.4349 0.2496 0.105 Uiso calc R 1 H
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C7 O2 H2A 109.5 ?
C9 O3 H3A 109.5 ?
C2 C1 C14 119.84(15) ?
C2 C1 H1 120.1 ?
C14 C1 H1 120.1 ?
C3 C2 C1 120.59(13) ?
C3 C2 H2 119.7 ?
C1 C2 H2 119.7 ?
C2 C3 C4 120.17(14) ?
C2 C3 H3 119.9 ?
C4 C3 H3 119.9 ?
C3 C4 C13 119.56(13) ?
C3 C4 C5 119.31(12) ?
C13 C4 C5 121.13(11) ?
O1 C5 C6 121.75(12) ?
O1 C5 C4 119.94(11) ?
C6 C5 C4 118.31(11) ?
C7 C6 C11 118.30(11) ?
C7 C6 C5 120.44(11) ?
C11 C6 C5 121.26(11) ?
O2 C7 C6 121.55(11) y
O2 C7 C8 116.54(12) y
C6 C7 C8 121.90(11) ?
C9 C8 C7 117.58(12) ?
C9 C8 C15 121.52(12) ?
C7 C8 C15 120.89(12) ?
O3 C9 C8 116.73(12) y
O3 C9 C10 121.46(11) y
C8 C9 C10 121.81(11) ?
C11 C10 C9 120.09(11) ?
C11 C10 H10 120.0 ?
C9 C10 H10 120.0 ?
C10 C11 C6 120.31(11) ?
C10 C11 C12 119.03(10) ?
C6 C11 C12 120.66(10) ?
O4 C12 C13 121.16(12) ?
O4 C12 C11 120.98(11) ?
C13 C12 C11 117.85(10) ?
C14 C13 C4 119.51(12) ?
C14 C13 C12 119.78(12) ?
C4 C13 C12 120.71(12) ?
C13 C14 C1 120.32(14) ?
C13 C14 H14 119.8 ?
C1 C14 H14 119.8 ?
C8 C15 H15A 109.5 ?
C8 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C8 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 1.2408(14) y
O2 C7 1.3501(14) y
O2 H2A 0.82 ?
O3 C9 1.3566(15) y
O3 H3A 0.82 ?
O4 C12 1.2255(14) y
C1 C2 1.380(2) ?
C1 C14 1.389(2) ?
C1 H1 0.93 ?
C2 C3 1.376(2) ?
C2 H2 0.93 ?
C3 C4 1.3934(18) ?
C3 H3 0.93 ?
C4 C13 1.4005(18) ?
C4 C5 1.4846(19) ?
C5 C6 1.4548(17) ?
C6 C7 1.4037(18) ?
C6 C11 1.4130(16) ?
C7 C8 1.4053(19) ?
C8 C9 1.3892(17) ?
C8 C15 1.499(2) ?
C9 C10 1.3928(18) ?
C10 C11 1.3790(17) ?
C10 H10 0.93 ?
C11 C12 1.4839(17) ?
C12 C13 1.4826(17) ?
C13 C14 1.3875(19) ?
C14 H14 0.93 ?
C15 H15A 0.96 ?
C15 H15B 0.96 ?
C15 H15C 0.96 ?
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
O2 H2A O1 1_555 0.82 1.84 2.567(2) 147 y
C15 H15A O3 1_555 0.96 2.41 2.784(2) 103 y
O3 H3A O4 3_566 0.82 1.98 2.7960(10) 171 y
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
C14 C1 C2 C3 0.1(2)
C1 C2 C3 C4 -0.8(2)
C2 C3 C4 C13 0.8(2)
C2 C3 C4 C5 -179.53(12)
C3 C4 C5 O1 -0.03(19)
C13 C4 C5 O1 179.67(11)
C3 C4 C5 C6 179.42(11)
C13 C4 C5 C6 -0.89(18)
O1 C5 C6 C7 0.35(19)
C4 C5 C6 C7 -179.08(11)
O1 C5 C6 C11 179.45(11)
C4 C5 C6 C11 0.01(18)
C11 C6 C7 O2 179.03(11)
C5 C6 C7 O2 -1.85(19)
C11 C6 C7 C8 -0.50(19)
C5 C6 C7 C8 178.62(11)
O2 C7 C8 C9 -179.55(12)
C6 C7 C8 C9 0.0(2)
O2 C7 C8 C15 -0.1(2)
C6 C7 C8 C15 179.41(14)
C7 C8 C9 O3 -179.69(11)
C15 C8 C9 O3 0.9(2)
C7 C8 C9 C10 0.2(2)
C15 C8 C9 C10 -179.22(13)
O3 C9 C10 C11 -179.98(11)
C8 C9 C10 C11 0.16(19)
C9 C10 C11 C6 -0.68(18)
C9 C10 C11 C12 178.82(10)
C7 C6 C11 C10 0.84(18)
C5 C6 C11 C10 -178.28(10)
C7 C6 C11 C12 -178.65(10)
C5 C6 C11 C12 2.23(18)
C10 C11 C12 O4 -3.70(18)
C6 C11 C12 O4 175.79(11)
C10 C11 C12 C13 176.96(10)
C6 C11 C12 C13 -3.55(17)
C3 C4 C13 C14 0.02(19)
C5 C4 C13 C14 -179.67(11)
C3 C4 C13 C12 179.17(11)
C5 C4 C13 C12 -0.52(18)
O4 C12 C13 C14 2.50(19)
C11 C12 C13 C14 -178.17(11)
O4 C12 C13 C4 -176.65(11)
C11 C12 C13 C4 2.69(17)
C4 C13 C14 C1 -0.8(2)
C12 C13 C14 C1 -179.93(12)
C2 C1 C14 C13 0.7(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 110563
