#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/20/2232073.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_2232073
loop_
_publ_author_name
'Nargis, Jamila'
'Wong, Keng-Chong'
'Khairuddin, Melati'
'Chantrapromma, Suchada'
'Fun, Hoong-Kun'
_publ_section_title
;
 (2,4-Dihydroxy-6-methoxyphenyl)(3,5-dihydroxyphenyl)methanone monohydrate
;
_journal_coeditor_code           TK2790
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2717
_journal_page_last               o2718
_journal_paper_doi               10.1107/S1600536811037913
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H12 O6, H2 O'
_chemical_formula_moiety         'C14 H12 O6, H2 O'
_chemical_formula_sum            'C14 H14 O7'
_chemical_formula_weight         294.25
_chemical_melting_point_gt       516
_chemical_melting_point_lt       519
_chemical_name_systematic
;
(2,4-Dihydroxy-6-methoxyphenyl)(3,5-dihydroxyphenyl)methanone 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                82.4010(10)
_cell_angle_beta                 75.5700(10)
_cell_angle_gamma                67.8420(10)
_cell_formula_units_Z            2
_cell_length_a                   7.70870(10)
_cell_length_b                   8.40500(10)
_cell_length_c                   11.23800(10)
_cell_measurement_reflns_used    4696
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.50
_cell_measurement_theta_min      1.87
_cell_volume                     652.486(14)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19157
_diffrn_reflns_theta_full        32.50
_diffrn_reflns_theta_max         32.50
_diffrn_reflns_theta_min         1.87
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9882
_exptl_absorpt_correction_T_min  0.9508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.307
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0380P)²+0.6330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1311
_reflns_number_gt                4220
_reflns_number_total             4696
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2790.cif
_cod_data_source_block           I
_cod_original_cell_volume        652.486(13)
_cod_database_code               2232073
_cod_database_fobs_code          2232073
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.02024(14) 0.10822(14) 0.58801(9) 0.01558(19) Uani d . 1 1 . .
O O2 0.18999(14) 0.13186(13) 0.36467(9) 0.01292(18) Uani d . 1 1 . .
H H1O2 0.114(4) 0.106(4) 0.432(3) 0.044(7) Uiso d . 1 1 . .
O O3 0.74976(15) 0.27372(15) 0.28766(10) 0.0168(2) Uani d . 1 1 . .
H H1O3 0.757(4) 0.250(3) 0.215(2) 0.032(6) Uiso d . 1 1 . .
O O4 0.40238(14) 0.24500(14) 0.69771(9) 0.01396(19) Uani d . 1 1 . .
O O5 -0.23219(17) 0.21024(15) 1.05072(9) 0.0191(2) Uani d . 1 1 . .
H H1O5 -0.247(4) 0.123(3) 1.035(2) 0.036(7) Uiso d . 1 1 . .
O O6 -0.12705(15) 0.70856(13) 0.85592(10) 0.01557(19) Uani d . 1 1 . .
H H1O6 -0.114(4) 0.751(4) 0.789(3) 0.040(7) Uiso d . 1 1 . .
C C1 0.27991(17) 0.20544(16) 0.53565(11) 0.0104(2) Uani d . 1 1 . .
C C2 0.31206(17) 0.17912(16) 0.40884(11) 0.0106(2) Uani d . 1 1 . .
C C3 0.46478(18) 0.20447(17) 0.32314(12) 0.0125(2) Uani d . 1 1 . .
H H3A 0.4796 0.1921 0.2380 0.015 Uiso calc R 1 1 . .
C C4 0.59587(18) 0.24845(17) 0.36499(12) 0.0121(2) Uani d . 1 1 . .
C C5 0.57783(18) 0.26523(17) 0.49021(12) 0.0128(2) Uani d . 1 1 . .
H H5A 0.6706 0.2921 0.5172 0.015 Uiso calc R 1 1 . .
C C6 0.42273(17) 0.24217(16) 0.57445(11) 0.0110(2) Uani d . 1 1 . .
C C7 0.10655(17) 0.19008(16) 0.61790(12) 0.0110(2) Uani d . 1 1 . .
C C8 0.01674(17) 0.28193(16) 0.73582(11) 0.0107(2) Uani d . 1 1 . .
C C9 -0.06148(18) 0.19737(17) 0.83798(12) 0.0126(2) Uani d . 1 1 . .
H H9A -0.0505 0.0816 0.8341 0.015 Uiso calc R 1 1 . .
C C10 -0.15600(19) 0.28606(17) 0.94574(12) 0.0131(2) Uani d . 1 1 . .
C C11 -0.17726(19) 0.45713(17) 0.95104(12) 0.0137(2) Uani d . 1 1 . .
H H11A -0.2429 0.5169 1.0247 0.016 Uiso calc R 1 1 . .
C C12 -0.10135(18) 0.53944(16) 0.84732(12) 0.0117(2) Uani d . 1 1 . .
C C13 -0.00183(18) 0.45267(17) 0.73944(12) 0.0120(2) Uani d . 1 1 . .
H H13A 0.0524 0.5089 0.6696 0.014 Uiso calc R 1 1 . .
C C14 0.54604(19) 0.27856(19) 0.73956(13) 0.0159(2) Uani d . 1 1 . .
H H14A 0.5188 0.2715 0.8297 0.024 Uiso calc R 1 1 . .
H H14B 0.5450 0.3939 0.7101 0.024 Uiso calc R 1 1 . .
H H14C 0.6725 0.1932 0.7076 0.024 Uiso calc R 1 1 . .
O O1W 0.6637(7) 0.9646(10) 0.0189(7) 0.0211(11) Uani d P 0.555(19) 1 A 1
H H1W1 0.7461 0.8666 -0.0151 0.032 Uiso d PR 0.555(19) 1 A 1
H H2W1 0.5642 0.9957 -0.0002 0.032 Uiso d PR 0.555(19) 1 A 1
O O1WX 0.6960(8) 0.9169(9) 0.0518(6) 0.0125(9) Uani d P 0.445(19) 1 A 2
H H1WX 0.6896 0.8759 0.1225 0.019 Uiso d PR 0.445(19) 1 A 2
H H2WX 0.7964 0.8353 0.0173 0.019 Uiso d PR 0.445(19) 1 A 2
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
C2 O2 H1O2 104.3(18)
C4 O3 H1O3 109.9(16)
C6 O4 C14 117.37(10)
C10 O5 H1O5 110.8(18)
C12 O6 H1O6 109(2)
C2 C1 C6 116.96(11)
C2 C1 C7 118.58(11)
C6 C1 C7 124.45(11)
O2 C2 C3 116.67(11)
O2 C2 C1 121.07(11)
C3 C2 C1 122.23(11)
C2 C3 C4 118.45(12)
C2 C3 H3A 120.8
C4 C3 H3A 120.8
O3 C4 C3 122.18(12)
O3 C4 C5 116.18(11)
C3 C4 C5 121.63(12)
C6 C5 C4 119.19(12)
C6 C5 H5A 120.4
C4 C5 H5A 120.4
O4 C6 C5 122.54(11)
O4 C6 C1 116.13(11)
C5 C6 C1 121.26(12)
O1 C7 C1 120.63(11)
O1 C7 C8 117.04(11)
C1 C7 C8 122.17(11)
C13 C8 C9 121.23(12)
C13 C8 C7 120.11(11)
C9 C8 C7 118.45(11)
C10 C9 C8 118.71(12)
C10 C9 H9A 120.6
C8 C9 H9A 120.6
O5 C10 C11 116.99(12)
O5 C10 C9 122.05(12)
C11 C10 C9 120.96(12)
C12 C11 C10 119.21(12)
C12 C11 H11A 120.4
C10 C11 H11A 120.4
O6 C12 C11 117.41(11)
O6 C12 C13 121.52(12)
C11 C12 C13 121.06(12)
C12 C13 C8 118.81(12)
C12 C13 H13A 120.6
C8 C13 H13A 120.6
O4 C14 H14A 109.5
O4 C14 H14B 109.5
H14A C14 H14B 109.5
O4 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
H1W1 O1W H2W1 112.7
H1WX O1WX H2WX 97.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2437(16)
O2 C2 1.3626(15)
O2 H1O2 0.89(3)
O3 C4 1.3546(15)
O3 H1O3 0.85(3)
O4 C6 1.3570(15)
O4 C14 1.4344(16)
O5 C10 1.3715(16)
O5 H1O5 0.83(3)
O6 C12 1.3724(16)
O6 H1O6 0.79(3)
C1 C2 1.4168(17)
C1 C6 1.4244(17)
C1 C7 1.4628(17)
C2 C3 1.3888(17)
C3 C4 1.3942(18)
C3 H3A 0.9500
C4 C5 1.3998(18)
C5 C6 1.3876(17)
C5 H5A 0.9500
C7 C8 1.4972(18)
C8 C13 1.3925(18)
C8 C9 1.3961(17)
C9 C10 1.3937(18)
C9 H9A 0.9500
C10 C11 1.3920(19)
C11 C12 1.3900(18)
C11 H11A 0.9500
C12 C13 1.3923(17)
C13 H13A 0.9500
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
O1W H1W1 0.8916
O1W H2W1 0.7867
O1WX H1WX 0.8209
O1WX H2WX 0.8602
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 H1O2 O1 1_555 0.89(3) 1.72(3) 2.5453(14) 152(3) y
O2 H1O2 O1 2_556 0.89(3) 2.45(3) 2.9554(16) 117(3) y
O3 H1O3 O5 1_654 0.85(2) 1.90(2) 2.7440(15) 177(3) y
O5 H1O5 O1W 1_446 0.83(3) 1.76(3) 2.574(7) 166(3) y
O6 H1O6 O2 2_566 0.79(3) 1.98(3) 2.7220(15) 157(3) y
O1W H1W1 O6 1_654 0.89 1.91 2.746(8) 156 y
C14 H14C O1 1_655 0.98 2.55 3.4507(19) 152 y
O1WX H2WX Cg2 2_666 0.86 2.89 3.402(7) 120 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
C6 C1 C2 O2 175.50(11)
C7 C1 C2 O2 -3.32(18)
C6 C1 C2 C3 -6.35(19)
C7 C1 C2 C3 174.83(12)
O2 C2 C3 C4 -178.32(11)
C1 C2 C3 C4 3.46(19)
C2 C3 C4 O3 179.32(12)
C2 C3 C4 C5 0.8(2)
O3 C4 C5 C6 179.57(12)
C3 C4 C5 C6 -1.8(2)
C14 O4 C6 C5 1.91(18)
C14 O4 C6 C1 178.89(11)
C4 C5 C6 O4 175.49(12)
C4 C5 C6 C1 -1.3(2)
C2 C1 C6 O4 -171.78(11)
C7 C1 C6 O4 6.96(19)
C2 C1 C6 C5 5.23(19)
C7 C1 C6 C5 -176.02(12)
C2 C1 C7 O1 21.15(19)
C6 C1 C7 O1 -157.57(13)
C2 C1 C7 C8 -154.00(12)
C6 C1 C7 C8 27.27(19)
O1 C7 C8 C13 -132.18(13)
C1 C7 C8 C13 43.14(18)
O1 C7 C8 C9 42.51(17)
C1 C7 C8 C9 -142.18(13)
C13 C8 C9 C10 -1.36(19)
C7 C8 C9 C10 -175.99(11)
C8 C9 C10 O5 -178.31(12)
C8 C9 C10 C11 1.8(2)
O5 C10 C11 C12 179.54(12)
C9 C10 C11 C12 -0.5(2)
C10 C11 C12 O6 179.35(12)
C10 C11 C12 C13 -1.2(2)
O6 C12 C13 C8 -178.96(12)
C11 C12 C13 C8 1.58(19)
C9 C8 C13 C12 -0.30(19)
C7 C8 C13 C12 174.24(11)
