#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/03/2200312.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_2200312
loop_
_publ_author_name
'Hansen, Lars Kr.'
'Perlovich, German L.'
'Bauer-Brandl, Annette'
_publ_section_title
;
 The 1:1 hydrate of diflunisal
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o477
_journal_page_last               o479
_journal_paper_doi               10.1107/S1600536801006973
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C13 H8 F2 O3, H2 O1'
_chemical_formula_moiety         'C13 H8 F2 O3, H2 O1'
_chemical_formula_sum            'C13 H10 F2 O4'
_chemical_formula_weight         268.21
_chemical_name_common            'diflunisal hydrate'
_chemical_name_systematic
;
2',4'-Difluoro-4-hydroxybiphenyl-3-carboxylic acid hydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.47(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   34.650(2)
_cell_length_b                   3.730(2)
_cell_length_c                   20.760(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      16
_cell_measurement_theta_min      12
_cell_volume                     2513.7(17)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'OSCAIL (McArdle, 1993)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full .998
_diffrn_measured_fraction_theta_max .998
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .0142
_diffrn_reflns_av_sigmaI/netI    .0377
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            2306
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.25
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .124
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .15
_refine_diff_density_max         .257
_refine_diff_density_min         -.158
_refine_ls_extinction_coef       .0019(10)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   .826
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2221
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      .836
_refine_ls_R_factor_all          .0995
_refine_ls_R_factor_gt           .0496
_refine_ls_shift/su_max          .072
_refine_ls_shift/su_mean         .005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1388P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1776
_reflns_number_gt                1127
_reflns_number_total             2221
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6069.cif
_cod_data_source_block           I
_cod_original_cell_volume        2513.7(14)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2200312
_cod_database_fobs_code          2200312
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O2 .21016(6) .4183(7) .51319(10) .0799(7) Uani d . 1 . . O
O1 .14124(7) .6837(7) .51807(10) .0803(7) Uani d . 1 . . O
F1 .04258(6) .7662(6) .01551(9) .1004(8) Uani d . 1 . . F
O3 .21697(6) .3433(6) .41116(10) .0744(7) Uani d . 1 . . O
F22 .14811(9) .9780(9) .22339(15) .0729(9) Uani d P .50 . . F
F21 .02001(9) .4863(9) .21767(16) .0710(9) Uani d P .50 . . F
O1W .2503(14) .30(2) .2028(17) .61(4) Uani d PU .35 . . O
H11W .2347 .1304 .1861 .22(7) Uiso calc PR .50 . . H
H21W .2221 .4924 .1899 .10(2) Uiso d PR .50 . . H
O2W .2684(12) .03(2) .284(2) .81(6) Uani d PU .65 . . O
H12W .2842 -.0501 .2660 .21(6) Uiso calc PR .50 . . H
H22W .2717 .2020 .3112 .14(4) Uiso d PR .50 . . H
H2O .2441(11) .247(9) .4415(16) .090(10) Uiso d . 1 . . H
H1O .1735(17) .594(18) .545(3) .20(2) Uiso d . 1 . . H
H12 .0012(9) .565(8) .0892(14) .078(8) Uiso d . 1 . . H
H6 .0475(9) .933(8) .3163(13) .070(8) Uiso d . 1 . . H
H2 .1563(7) .512(7) .3167(12) .054(7) Uiso d . 1 . . H
H10 .1109(9) .940(8) .0936(14) .072(8) Uiso d . 1 . . H
H5 .0757(8) .897(8) .4393(14) .073(8) Uiso d . 1 . . H
C1 .10061(7) .7280(6) .30416(13) .0523(7) Uani d . 1 . . C
C2 .13952(8) .6003(7) .34099(13) .0531(7) Uani d . 1 . . C
C3 .15455(7) .5818(7) .41225(13) .0544(7) Uani d . 1 . . C
C4 .12911(8) .6963(7) .44856(14) .0583(7) Uani d . 1 . . C
C5 .09024(8) .8234(8) .41219(15) .0603(7) Uani d . 1 . . C
C6 .07633(8) .8403(7) .34188(14) .0570(7) Uani d . 1 . . C
C7 .19583(8) .4423(8) .44992(14) .0604(7) Uani d . 1 . . C
C8 .08514(8) .7419(6) .22797(13) .0523(7) Uani d . 1 . . C
C9 .10952(8) .8607(8) .19111(14) .0594(7) Uani d . 1 . . C
C10 .09597(9) .8707(9) .12048(15) .0675(8) Uani d . 1 . . C
C11 .05671(10) .7592(8) .08547(14) .0697(8) Uani d . 1 . . C
C12 .03057(9) .6409(9) .11752(15) .0668(8) Uani d . 1 . . C
C13 .04560(8) .6320(8) .18820(13) .0581(7) Uani d . 1 . . C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F .0171 .0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C4 O1 H1O . 116(3)
C7 O3 H2O . 108.5(17)
O2W O1W H11W 4 109.6
O2W O1W H21W 4 27.1
H11W O1W H21W . 90.3
O1W O2W H12W 4_545 109.4
O1W O2W H22W 4_545 110.9
H12W O2W H22W . 130.2
C2 C1 C6 . 117.1(2)
C2 C1 C8 . 121.4(2)
C6 C1 C8 . 121.5(2)
C1 C2 C3 . 122.5(2)
C1 C2 H2 . 118.9(14)
C3 C2 H2 . 118.5(14)
C2 C3 C4 . 118.9(2)
C2 C3 C7 . 121.3(2)
C4 C3 C7 . 119.9(2)
O1 C4 C5 . 118.4(2)
O1 C4 C3 . 122.6(2)
C5 C4 C3 . 119.0(3)
C6 C5 C4 . 120.8(3)
C6 C5 H5 . 125.1(17)
C4 C5 H5 . 114.1(17)
C5 C6 C1 . 121.8(3)
C5 C6 H6 . 119.2(14)
C1 C6 H6 . 119.0(15)
O2 C7 O3 . 121.8(3)
O2 C7 C3 . 123.2(2)
O3 C7 C3 . 114.9(2)
C13 C8 C9 . 115.3(2)
C13 C8 C1 . 122.4(2)
C9 C8 C1 . 122.3(2)
F22 C9 C10 . 115.6(3)
F22 C9 C8 . 121.2(3)
C10 C9 C8 . 123.2(3)
C11 C10 C9 . 117.7(3)
C11 C10 H10 . 115.5(17)
C9 C10 H10 . 126.8(18)
F1 C11 C10 . 118.8(3)
F1 C11 C12 . 118.2(3)
C10 C11 C12 . 123.0(3)
C11 C12 C13 . 117.3(3)
C11 C12 H12 . 120.3(16)
C13 C12 H12 . 122.4(16)
F21 C13 C12 . 115.4(3)
F21 C13 C8 . 121.0(3)
C12 C13 C8 . 123.6(2)
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
O2 C7 . 1.234(3) ?
O1 C4 . 1.355(3) ?
O1 H1O . 1.11(6) ?
F1 C11 . 1.361(3) ?
O3 C7 . 1.316(3) ?
O3 H2O . 1.00(3) ?
F22 C9 . 1.343(4) ?
F21 C13 . 1.355(4) ?
O1W O2W 4 1.18(4) ?
O1W H11W . .8200 ?
O1W H21W . 1.1686 ?
O2W O1W 4_545 1.18(4) ?
O2W H12W . .8200 ?
O2W H22W . .8297 ?
C1 C2 . 1.381(4) ?
C1 C6 . 1.399(3) ?
C1 C8 . 1.483(4) ?
C2 C3 . 1.388(4) ?
C2 H2 . .95(2) ?
C3 C4 . 1.411(3) ?
C3 C7 . 1.465(4) ?
C4 C5 . 1.378(4) ?
C5 C6 . 1.369(4) ?
C5 H5 . .92(3) ?
C6 H6 . 1.02(3) ?
C8 C13 . 1.391(4) ?
C8 C9 . 1.395(4) ?
C9 C10 . 1.375(4) ?
C10 C11 . 1.364(4) ?
C10 H10 . .92(3) ?
C11 C12 . 1.371(4) ?
C12 C13 . 1.375(4) ?
C12 H12 . 1.02(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
_geom_hbond_publ_flag
O3 H2O O2 7_556 1.00(4) 1.65(4) 2.650(3) 176(4) yes
O1 H1O O2 . 1.11(6) 1.75(6) 2.620(4) 131(4) yes
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 C3 .0(4)
C8 C1 C2 C3 -179.5(2)
C1 C2 C3 C4 .3(4)
C1 C2 C3 C7 179.5(2)
C2 C3 C4 O1 179.3(3)
C7 C3 C4 O1 .1(4)
C2 C3 C4 C5 -.2(4)
C7 C3 C4 C5 -179.4(3)
O1 C4 C5 C6 -179.7(3)
C3 C4 C5 C6 -.2(4)
C4 C5 C6 C1 .5(4)
C2 C1 C6 C5 -.3(4)
C8 C1 C6 C5 179.1(2)
C2 C3 C7 O2 -179.3(3)
C4 C3 C7 O2 -.1(4)
C2 C3 C7 O3 .9(4)
C4 C3 C7 O3 -180.0(2)
C2 C1 C8 C13 135.7(3)
C6 C1 C8 C13 -43.7(3)
C2 C1 C8 C9 -43.2(3)
C6 C1 C8 C9 137.4(3)
C13 C8 C9 F22 179.2(3)
C1 C8 C9 F22 -1.9(4)
C13 C8 C9 C10 .1(4)
C1 C8 C9 C10 179.0(3)
F22 C9 C10 C11 -179.0(3)
C8 C9 C10 C11 .2(5)
C9 C10 C11 F1 -179.9(3)
C9 C10 C11 C12 .3(5)
F1 C11 C12 C13 179.3(3)
C10 C11 C12 C13 -1.0(5)
C11 C12 C13 F21 -174.8(3)
C11 C12 C13 C8 1.2(5)
C9 C8 C13 F21 175.1(3)
C1 C8 C13 F21 -3.9(4)
C9 C8 C13 C12 -.8(4)
C1 C8 C13 C12 -179.7(3)
