#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/93/2229391.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_2229391
loop_
_publ_author_name
'Wang, Jian-Guo'
'Wu, Lin'
'Zhong, Chan-Juan'
'Ouyang, Zhao-Hui'
'Yi, De-Lian'
_publ_section_title
;
 (E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
 monohydrate
;
_journal_coeditor_code           GO2004
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o732
_journal_paper_doi               10.1107/S1600536811006271
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H12 O4, H2 O'
_chemical_formula_moiety         'C15 H12 O4, H2 O'
_chemical_formula_sum            'C15 H14 O5'
_chemical_formula_weight         274.26
_chemical_name_systematic
;
(E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
monohydrate
;
_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                 103.649(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.489(2)
_cell_length_b                   9.5903(17)
_cell_length_c                   12.498(2)
_cell_measurement_reflns_used    2288
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.28
_cell_measurement_theta_min      2.71
_cell_volume                     1338.2(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8297
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_correction_T_min  0.9878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.192
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2625
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0571
_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)+(0.0569P)²+0.4990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                2115
_reflns_number_total             2625
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            go2004.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229391
_cod_database_fobs_code          2229391
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_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 0.19653(18) 1.0001(2) 0.07068(17) 0.0402(5) Uani d . 1 . .
C C2 0.10947(18) 1.1026(2) 0.07420(17) 0.0412(5) Uani d . 1 . .
C C3 0.0605(2) 1.1156(2) 0.16459(19) 0.0475(6) Uani d . 1 . .
H H3 0.0037 1.1844 0.1655 0.057 Uiso calc R 1 . .
C C4 0.0950(2) 1.0275(2) 0.25329(18) 0.0452(5) Uani d . 1 . .
C C5 0.1818(2) 0.9256(3) 0.25306(19) 0.0500(6) Uani d . 1 . .
H H5 0.2061 0.8663 0.3131 0.060 Uiso calc R 1 . .
C C6 0.2309(2) 0.9138(2) 0.16359(19) 0.0473(6) Uani d . 1 . .
H H6 0.2892 0.8462 0.1644 0.057 Uiso calc R 1 . .
C C7 0.24678(19) 0.9881(2) -0.02538(18) 0.0437(5) Uani d . 1 . .
C C8 0.3403(2) 0.8856(3) -0.02910(19) 0.0494(6) Uani d . 1 . .
H H8 0.3588 0.8183 0.0258 0.059 Uiso calc R 1 . .
C C9 0.3990(2) 0.8858(3) -0.10772(19) 0.0493(6) Uani d . 1 . .
H H9 0.3751 0.9540 -0.1613 0.059 Uiso calc R 1 . .
C C10 0.49523(19) 0.7959(2) -0.12387(17) 0.0431(5) Uani d . 1 . .
C C11 0.5467(2) 0.6925(3) -0.05077(19) 0.0566(7) Uani d . 1 . .
H H11 0.5169 0.6760 0.0111 0.068 Uiso calc R 1 . .
C C12 0.6406(2) 0.6134(3) -0.0672(2) 0.0635(7) Uani d . 1 . .
H H12 0.6750 0.5458 -0.0161 0.076 Uiso calc R 1 . .
C C13 0.68407(19) 0.6350(3) -0.16102(18) 0.0474(6) Uani d . 1 . .
C C14 0.6341(2) 0.7353(3) -0.23509(18) 0.0486(6) Uani d . 1 . .
H H14 0.6628 0.7498 -0.2978 0.058 Uiso calc R 1 . .
C C15 0.5412(2) 0.8148(3) -0.21662(19) 0.0518(6) Uani d . 1 . .
H H15 0.5080 0.8832 -0.2675 0.062 Uiso calc R 1 . .
O O1 0.07099(15) 1.19360(19) -0.01001(14) 0.0589(5) Uani d D 1 . .
H H1A 0.107(3) 1.171(3) -0.061(2) 0.088 Uiso d D 1 . .
O O2 0.04269(18) 1.0443(2) 0.33756(14) 0.0649(5) Uani d D 1 . .
H H2A 0.069(3) 0.988(3) 0.387(2) 0.097 Uiso d D 1 . .
O O3 0.21067(14) 1.06876(19) -0.10709(13) 0.0565(5) Uani d . 1 . .
O O4 0.77775(17) 0.5545(2) -0.17385(14) 0.0668(6) Uani d D 1 . .
H H4A 0.784(3) 0.563(4) -0.2384(17) 0.100 Uiso d D 1 . .
O O5 0.12061(17) 0.6281(2) 0.00416(14) 0.0587(5) Uani d D 1 . .
H H5A 0.072(2) 0.687(3) 0.017(3) 0.088 Uiso d D 1 . .
H H5B 0.149(3) 0.586(3) 0.0630(19) 0.088 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
C6 C1 C2 . . 116.61(18) ?
C6 C1 C7 . . 123.2(2) ?
C2 C1 C7 . . 120.24(19) ?
O1 C2 C3 . . 117.03(19) ?
O1 C2 C1 . . 121.81(18) ?
C3 C2 C1 . . 121.2(2) ?
C4 C3 C2 . . 120.5(2) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
O2 C4 C3 . . 117.5(2) ?
O2 C4 C5 . . 122.6(2) ?
C3 C4 C5 . . 119.90(19) ?
C6 C5 C4 . . 119.4(2) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C5 C6 C1 . . 122.4(2) ?
C5 C6 H6 . . 118.8 ?
C1 C6 H6 . . 118.8 ?
O3 C7 C1 . . 119.85(19) ?
O3 C7 C8 . . 119.07(19) ?
C1 C7 C8 . . 121.1(2) ?
C9 C8 C7 . . 122.1(2) ?
C9 C8 H8 . . 119.0 ?
C7 C8 H8 . . 119.0 ?
C8 C9 C10 . . 130.0(2) ?
C8 C9 H9 . . 115.0 ?
C10 C9 H9 . . 115.0 ?
C11 C10 C15 . . 117.1(2) ?
C11 C10 C9 . . 123.66(19) ?
C15 C10 C9 . . 119.2(2) ?
C12 C11 C10 . . 121.7(2) ?
C12 C11 H11 . . 119.1 ?
C10 C11 H11 . . 119.1 ?
C11 C12 C13 . . 119.6(2) ?
C11 C12 H12 . . 120.2 ?
C13 C12 H12 . . 120.2 ?
C14 C13 O4 . . 122.43(19) ?
C14 C13 C12 . . 119.9(2) ?
O4 C13 C12 . . 117.6(2) ?
C13 C14 C15 . . 119.7(2) ?
C13 C14 H14 . . 120.1 ?
C15 C14 H14 . . 120.1 ?
C14 C15 C10 . . 121.9(2) ?
C14 C15 H15 . . 119.0 ?
C10 C15 H15 . . 119.0 ?
C2 O1 H1A . . 107(2) ?
C4 O2 H2A . . 111(3) ?
C13 O4 H4A . . 108(2) ?
H5A O5 H5B . . 107(3) ?
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 C6 . 1.405(3) ?
C1 C2 . 1.410(3) ?
C1 C7 . 1.454(3) ?
C2 O1 . 1.359(3) ?
C2 C3 . 1.382(3) ?
C3 C4 . 1.375(3) ?
C3 H3 . 0.9300 ?
C4 O2 . 1.340(3) ?
C4 C5 . 1.397(3) ?
C5 C6 . 1.371(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O3 . 1.270(3) ?
C7 C8 . 1.465(3) ?
C8 C9 . 1.316(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.453(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.383(3) ?
C10 C15 . 1.394(3) ?
C11 C12 . 1.374(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.393(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.364(3) ?
C13 O4 . 1.364(3) ?
C14 C15 . 1.375(3) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
O1 H1A . 0.867(18) ?
O2 H2A . 0.819(18) ?
O4 H4A . 0.829(18) ?
O5 H5A . 0.836(18) ?
O5 H5B . 0.836(18) ?
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
O1 H1A O3 . 0.867(18) 1.74(2) 2.530(2) 150(3)
O2 H2A O5 4_576 0.819(18) 1.827(19) 2.644(3) 175(4)
O4 H4A O3 2_644 0.829(18) 1.948(19) 2.776(2) 175(4)
O5 H5A O1 3_575 0.836(18) 1.989(19) 2.802(2) 164(3)
O5 H5B O4 3_665 0.836(18) 1.97(2) 2.785(3) 165(3)
C9 H9 O4 2_654 0.93 2.56 3.402(3) 151
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
C6 C1 C2 O1 . . . . 178.7(2) ?
C7 C1 C2 O1 . . . . -0.9(3) ?
C6 C1 C2 C3 . . . . -0.5(3) ?
C7 C1 C2 C3 . . . . 179.9(2) ?
O1 C2 C3 C4 . . . . -179.8(2) ?
C1 C2 C3 C4 . . . . -0.6(3) ?
C2 C3 C4 O2 . . . . -179.0(2) ?
C2 C3 C4 C5 . . . . 1.1(4) ?
O2 C4 C5 C6 . . . . 179.5(2) ?
C3 C4 C5 C6 . . . . -0.6(4) ?
C4 C5 C6 C1 . . . . -0.5(4) ?
C2 C1 C6 C5 . . . . 1.1(3) ?
C7 C1 C6 C5 . . . . -179.4(2) ?
C6 C1 C7 O3 . . . . 179.3(2) ?
C2 C1 C7 O3 . . . . -1.1(3) ?
C6 C1 C7 C8 . . . . -1.7(3) ?
C2 C1 C7 C8 . . . . 177.9(2) ?
O3 C7 C8 C9 . . . . 8.8(4) ?
C1 C7 C8 C9 . . . . -170.2(2) ?
C7 C8 C9 C10 . . . . 178.4(2) ?
C8 C9 C10 C11 . . . . -3.0(4) ?
C8 C9 C10 C15 . . . . 178.3(3) ?
C15 C10 C11 C12 . . . . 1.3(4) ?
C9 C10 C11 C12 . . . . -177.5(2) ?
C10 C11 C12 C13 . . . . -1.5(4) ?
C11 C12 C13 C14 . . . . 0.7(4) ?
C11 C12 C13 O4 . . . . 179.7(2) ?
O4 C13 C14 C15 . . . . -178.9(2) ?
C12 C13 C14 C15 . . . . 0.1(4) ?
C13 C14 C15 C10 . . . . -0.3(4) ?
C11 C10 C15 C14 . . . . -0.4(4) ?
C9 C10 C15 C14 . . . . 178.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656527
