#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/22/2222220.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_2222220
loop_
_publ_author_name
'Liu, Zhi-Meng'
'Jiao, Yuan-Qi'
_publ_section_title
;
 2-Hydroxy-1-methoxyanthraquinone monohydrate
;
_journal_coeditor_code           BG2258
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1523
_journal_paper_doi               10.1107/S1600536809021254
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H10 O4, H2 O'
_chemical_formula_moiety         'C15 H10 O4, H2 O'
_chemical_formula_sum            'C15 H12 O5'
_chemical_formula_weight         272.25
_chemical_name_systematic
;
2-Hydroxy-1-methoxyanthraquinone monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.462(3)
_cell_angle_beta                 102.364(3)
_cell_angle_gamma                100.653(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9583(19)
_cell_length_b                   8.269(2)
_cell_length_c                   10.188(2)
_cell_measurement_reflns_used    1018
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.18
_cell_measurement_theta_min      2.60
_cell_volume                     620.4(2)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEXII area-detector'
_diffrn_measurement_method       'φ and 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  0.0134
_diffrn_reflns_av_sigmaI/netI    0.0228
_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       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3218
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284.0
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2198
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0461
_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)+(0.0778P)²+0.0805P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1468
_reflns_number_gt                1488
_reflns_number_total             2198
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2258.cif
_cod_data_source_block           I
_cod_database_code               2222220
_cod_database_fobs_code          2222220
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C C1 0.6640(3) 0.3815(2) 0.3121(2) 0.0509(5) Uani d . 1 . .
C C2 0.7049(3) 0.2214(2) 0.30375(19) 0.0476(5) Uani d . 1 . .
C C3 0.7720(3) -0.0406(2) 0.1655(2) 0.0485(5) Uani d . 1 . .
C C4 0.8497(3) -0.2806(2) 0.0176(2) 0.0555(5) Uani d . 1 . .
H H4 0.8772 -0.3219 0.0955 0.067 Uiso calc R 1 . .
C C5 0.8632(3) -0.3695(3) -0.1086(3) 0.0645(6) Uani d . 1 . .
H H5 0.8980 -0.4717 -0.1158 0.077 Uiso calc R 1 . .
C C6 0.8257(3) -0.3093(3) -0.2248(3) 0.0668(6) Uani d . 1 . .
H H6 0.8347 -0.3707 -0.3099 0.080 Uiso calc R 1 . .
C C7 0.7746(3) -0.1565(3) -0.2142(2) 0.0600(6) Uani d . 1 . .
H H7 0.7505 -0.1146 -0.2921 0.072 Uiso calc R 1 . .
C C8 0.7044(3) 0.0971(2) -0.07708(19) 0.0500(5) Uani d . 1 . .
C C9 0.6444(3) 0.3450(2) 0.0710(2) 0.0514(5) Uani d . 1 . .
H H9 0.6210 0.3853 -0.0078 0.062 Uiso calc R 1 . .
C C10 0.6335(3) 0.4407(3) 0.1954(2) 0.0542(5) Uani d . 1 . .
H H10 0.6054 0.5458 0.2006 0.065 Uiso calc R 1 . .
C C11 0.7216(2) 0.1254(2) 0.17820(19) 0.0438(5) Uani d . 1 . .
C C12 0.6896(2) 0.1890(2) 0.06001(19) 0.0444(5) Uani d . 1 . .
C C13 0.7951(2) -0.1285(2) 0.0293(2) 0.0462(5) Uani d . 1 . .
C C14 0.7593(2) -0.0664(2) -0.08792(19) 0.0472(5) Uani d . 1 . .
C C15 0.8905(4) 0.2159(3) 0.5181(2) 0.0869(8) Uani d . 1 . .
H H15A 0.9726 0.1661 0.4763 0.130 Uiso calc R 1 . .
H H15B 0.8843 0.1791 0.6005 0.130 Uiso calc R 1 . .
H H15C 0.9298 0.3380 0.5425 0.130 Uiso calc R 1 . .
O O1 0.6741(2) 0.15409(19) -0.17812(15) 0.0741(5) Uani d . 1 . .
O O2 0.7941(3) -0.10671(19) 0.26171(16) 0.0772(5) Uani d . 1 . .
O O3 0.6543(2) 0.46790(18) 0.43714(14) 0.0679(5) Uani d . 1 . .
H H3 0.6315 0.5594 0.4317 0.102 Uiso calc R 1 . .
O O4 0.7180(2) 0.16259(18) 0.42088(14) 0.0616(4) Uani d . 1 . .
O O1W 0.5800(3) 0.7728(2) 0.44181(19) 0.0829(6) Uani d D 1 . .
H H1W 0.597(4) 0.844(4) 0.393(4) 0.162(15) Uiso d D 1 . .
H H2W 0.472(2) 0.762(4) 0.450(4) 0.134(14) Uiso d D 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 C1 C10 . . 123.24(18) ?
O3 C1 C2 . . 116.77(17) ?
C10 C1 C2 . . 119.98(18) ?
O4 C2 C11 . . 122.55(17) ?
O4 C2 C1 . . 117.08(17) ?
C11 C2 C1 . . 120.29(16) ?
O2 C3 C13 . . 119.21(18) ?
O2 C3 C11 . . 122.56(18) ?
C13 C3 C11 . . 118.22(16) ?
C5 C4 C13 . . 120.20(19) ?
C5 C4 H4 . . 119.9 ?
C13 C4 H4 . . 119.9 ?
C4 C5 C6 . . 120.9(2) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C5 C6 C7 . . 119.6(2) ?
C5 C6 H6 . . 120.2 ?
C7 C6 H6 . . 120.2 ?
C14 C7 C6 . . 120.1(2) ?
C14 C7 H7 . . 120.0 ?
C6 C7 H7 . . 119.9 ?
O1 C8 C12 . . 121.26(19) ?
O1 C8 C14 . . 120.74(18) ?
C12 C8 C14 . . 117.99(16) ?
C10 C9 C12 . . 121.52(18) ?
C10 C9 H9 . . 119.2 ?
C12 C9 H9 . . 119.2 ?
C9 C10 C1 . . 120.01(18) ?
C9 C10 H10 . . 120.0 ?
C1 C10 H10 . . 120.0 ?
C2 C11 C12 . . 118.56(17) ?
C2 C11 C3 . . 122.38(16) ?
C12 C11 C3 . . 119.06(17) ?
C9 C12 C11 . . 119.58(18) ?
C9 C12 C8 . . 117.85(17) ?
C11 C12 C8 . . 122.57(17) ?
C4 C13 C14 . . 118.95(18) ?
C4 C13 C3 . . 118.85(17) ?
C14 C13 C3 . . 122.18(17) ?
C7 C14 C13 . . 120.27(19) ?
C7 C14 C8 . . 119.88(18) ?
C13 C14 C8 . . 119.85(18) ?
O4 C15 H15A . . 109.5 ?
O4 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O4 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C1 O3 H3 . . 109.5 ?
C2 O4 C15 . . 115.30(16) ?
H1W O1W H2W . . 107.3(16) ?
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
C1 O3 . 1.345(2) ?
C1 C10 . 1.373(3) ?
C1 C2 . 1.410(3) ?
C2 O4 . 1.374(2) ?
C2 C11 . 1.399(3) ?
C3 O2 . 1.218(2) ?
C3 C13 . 1.487(3) ?
C3 C11 . 1.487(3) ?
C4 C5 . 1.373(3) ?
C4 C13 . 1.394(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.377(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.387(3) ?
C6 H6 . 0.9300 ?
C7 C14 . 1.382(3) ?
C7 H7 . 0.9300 ?
C8 O1 . 1.218(2) ?
C8 C12 . 1.479(3) ?
C8 C14 . 1.486(3) ?
C9 C10 . 1.371(3) ?
C9 C12 . 1.390(3) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C12 . 1.408(2) ?
C13 C14 . 1.395(3) ?
C15 O4 . 1.437(3) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
O3 H3 . 0.8200 ?
O1W H1W . 0.86(3) ?
O1W H2W . 0.87(3) ?
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
O1W H1W O2 1_565 0.86(3) 2.31(2) 2.960(3) 133(3)
O1W H2W O4 2_666 0.87(3) 2.30(2) 3.072(3) 149(3)
O3 H3 O1W . 0.82 1.87 2.687(2) 173.2
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
O3 C1 C2 O4 . . . . 4.7(3) ?
C10 C1 C2 O4 . . . . -174.23(17) ?
O3 C1 C2 C11 . . . . -178.49(17) ?
C10 C1 C2 C11 . . . . 2.6(3) ?
C13 C4 C5 C6 . . . . 1.0(3) ?
C4 C5 C6 C7 . . . . 0.3(3) ?
C5 C6 C7 C14 . . . . -0.7(3) ?
C12 C9 C10 C1 . . . . -1.3(3) ?
O3 C1 C10 C9 . . . . -179.48(18) ?
C2 C1 C10 C9 . . . . -0.6(3) ?
O4 C2 C11 C12 . . . . 174.08(16) ?
C1 C2 C11 C12 . . . . -2.5(3) ?
O4 C2 C11 C3 . . . . -6.0(3) ?
C1 C2 C11 C3 . . . . 177.34(16) ?
O2 C3 C11 C2 . . . . 3.3(3) ?
C13 C3 C11 C2 . . . . -176.94(16) ?
O2 C3 C11 C12 . . . . -176.78(18) ?
C13 C3 C11 C12 . . . . 2.9(3) ?
C10 C9 C12 C11 . . . . 1.3(3) ?
C10 C9 C12 C8 . . . . -177.90(17) ?
C2 C11 C12 C9 . . . . 0.6(3) ?
C3 C11 C12 C9 . . . . -179.25(16) ?
C2 C11 C12 C8 . . . . 179.82(16) ?
C3 C11 C12 C8 . . . . -0.1(3) ?
O1 C8 C12 C9 . . . . -1.6(3) ?
C14 C8 C12 C9 . . . . 177.72(16) ?
O1 C8 C12 C11 . . . . 179.19(17) ?
C14 C8 C12 C11 . . . . -1.5(3) ?
C5 C4 C13 C14 . . . . -1.7(3) ?
C5 C4 C13 C3 . . . . 176.53(17) ?
O2 C3 C13 C4 . . . . -3.0(3) ?
C11 C3 C13 C4 . . . . 177.29(16) ?
O2 C3 C13 C14 . . . . 175.24(18) ?
C11 C3 C13 C14 . . . . -4.5(3) ?
C6 C7 C14 C13 . . . . -0.1(3) ?
C6 C7 C14 C8 . . . . -179.97(18) ?
C4 C13 C14 C7 . . . . 1.3(3) ?
C3 C13 C14 C7 . . . . -176.93(17) ?
C4 C13 C14 C8 . . . . -178.80(17) ?
C3 C13 C14 C8 . . . . 3.0(3) ?
O1 C8 C14 C7 . . . . -0.7(3) ?
C12 C8 C14 C7 . . . . 179.92(16) ?
O1 C8 C14 C13 . . . . 179.34(18) ?
C12 C8 C14 C13 . . . . 0.0(3) ?
C11 C2 O4 C15 . . . . 95.3(2) ?
C1 C2 O4 C15 . . . . -87.9(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655801
