#------------------------------------------------------------------------------
#$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $
#$Revision: 88064 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/19/2011939.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_2011939
loop_
_publ_author_name
'Kashino, Setsuo'
'Fukunaga, Takeo'
'Izutsu, Hironobu'
'Miyashita, Shiho'
_publ_section_title
;
 Hydrogen-bonded complexes of 2-pyridone with centrosymmetric and
 non-centrosymmetric dicarboxylic acids
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              627
_journal_page_last               631
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C5 H5 N O , C4 H6 O6 , H2 O'
_chemical_formula_structural     'C5 H5 N O , C4 H6 O6 , H2 O'
_chemical_formula_sum            'C9 H13 N O8'
_chemical_formula_weight         263.20
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_type_scat_source           IntTabC
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.528(5)
_cell_length_b                   20.668(8)
_cell_length_c                   6.5438(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      11.5
_cell_measurement_theta_min      10.8
_cell_volume                     1153.4(9)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
 1990)
;
_computing_data_reduction
'TEXSAN for Windows (Molecular Structure Corporation, 1999)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'TEXSAN for Windows'
_computing_structure_refinement  'TEXSAN for Windows'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      295
_diffrn_measurement_device       'Rigaku AFC-5R'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .011
_diffrn_reflns_av_sigmaI/netI    .043
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2660
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         32.0
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%        <0.5
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .135
_exptl_absorpt_correction_T_max  .999
_exptl_absorpt_correction_T_min  .952
_exptl_absorpt_correction_type   '\y scans'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             552
_exptl_crystal_size_max          .53
_exptl_crystal_size_mid          .28
_exptl_crystal_size_min          .20
_refine_diff_density_max         .32
_refine_diff_density_min         -.31
_refine_ls_extinction_coef       '1.68 \\times 10(12)^-6^'
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   1.80
_refine_ls_goodness_of_fit_ref   1.81
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2064
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .047
_refine_ls_R_factor_gt           .044
_refine_ls_shift/su_max          .010
_refine_ls_shift/su_mean         .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00001|Fo|^2^]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         .046
_refine_ls_wR_factor_ref         .044
_reflns_number_gt                2064
_reflns_number_total             2303
_reflns_threshold_expression     I>0.1\s(I)
_[local]_cod_data_source_file    bk1582.cif
_[local]_cod_data_source_block   IV
_cod_original_cell_volume        1153.4(7)
_cod_database_code               2011939
loop_
_symmetry_equiv_pos_as_xyz
'  +x,  +y,  +z'
'1/2-x,  -y,1/2+z'
'1/2+x,1/2-y,  -z'
'  -x,1/2+y,1/2-z'
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_calc_attached_atom
_atom_site_refinement_flags
_atom_site_occupancy
O1 .49399(12) .43810(5) .25423(17) .0541(3) Uani d ? . 1.000
O2 .31341(10) .53184(5) .21738(18) .0558(3) Uani d ? . 1.000
O3 .51062(10) .60285(4) .19044(15) .0467(3) Uani d ? . 1.000
O4 .31260(12) .70141(5) .13139(18) .0496(3) Uani d ? . 1.000
O5 .25390(12) .66734(5) .53540(15) .0458(3) Uani d ? . 1.000
O6 -.09014(13) .66162(5) .22679(19) .0556(4) Uani d ? . 1.000
O7 -.01411(11) .73370(4) .46179(16) .0540(3) Uani d ? . 1.000
O8 -.34509(12) .73051(6) .1702(2) .0470(3) Uani d ? . 1.000
N1 .72157(13) .49451(6) .2167(2) .0423(4) Uani d ? . 1.000
C2 .64150(17) .43759(7) .2387(2) .0431(4) Uani d ? . 1.000
C3 .73498(19) .38140(7) .2403(3) .0488(5) Uani d ? . 1.000
C4 .89252(18) .38451(8) .2219(3) .0548(6) Uani d ? . 1.000
C5 .96815(19) .44382(9) .2021(3) .0518(5) Uani d ? . 1.000
C6 .88088(19) .49770(8) .1992(3) .0490(5) Uani d ? . 1.000
C7 .37157(17) .58980(7) .1943(2) .0409(4) Uani d ? . 1.000
C8 .24346(17) .64044(6) .1745(2) .0375(4) Uani d ? . 1.000
C9 .15579(16) .64452(7) .3785(2) .0369(4) Uani d ? . 1.000
C10 .00891(16) .68594(7) .3606(2) .0406(4) Uani d ? . 1.000
H1 .6595(14) .5334(6) .211(2) .059(5) Uiso d ? . 1.000
H2 .6820(14) .3442(5) .2578(19) .041(4) Uiso d ? . 1.000
H3 .9538(16) .3431(6) .227(2) .070(5) Uiso d ? . 1.000
H4 1.0811(15) .4476(6) .178(2) .062(5) Uiso d ? . 1.000
H5 .9227(12) .5395(5) .1839(19) .033(4) Uiso d ? . 1.000
H6 .1714(12) .6266(5) .0702(17) .027(4) Uiso d ? . 1.000
H7 .1185(11) .6012(4) .4129(15) .015(3) Uiso d ? . 1.000
H8 .2600(17) .7179(7) .045(3) .077(7) Uiso d ? . 1.000
H9 .318(2) .7022(8) .491(3) .145(9) Uiso d ? . 1.000
H10 .4094(19) .4904(8) .246(3) .101(6) Uiso d ? . 1.000
H11 -.1720(17) .6843(7) .219(3) .073(6) Uiso d ? . 1.000
H12 -.427(2) .7064(10) .156(4) .146(10) Uiso d ? . 1.000
H13 -.3645(19) .7532(7) .266(2) .074(7) Uiso d ? . 1.000
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 .0408(6) .0429(6) .0786(8) .0001(5) -.0053(6) -.0040(6)
O2 .0380(5) .0405(5) .0889(8) -.0019(5) .0013(6) -.0001(6)
O3 .0329(5) .0459(6) .0611(7) .0000(5) .0045(6) -.0007(6)
O4 .0455(6) .0484(6) .0549(8) -.0049(5) -.0052(6) .0161(6)
O5 .0402(6) .0524(6) .0449(6) -.0019(6) -.0059(6) -.0039(6)
O6 .0415(6) .0569(7) .0685(8) .0114(6) -.0137(7) -.0156(7)
O7 .0478(6) .0416(6) .0726(8) .0073(5) -.0033(6) -.0165(6)
O8 .0369(6) .0577(7) .0464(7) -.0031(6) .0040(6) -.0055(6)
N1 .0451(8) .0398(7) .0419(8) .0001(6) -.0015(7) -.0043(7)
C2 .0485(9) .0408(8) .0400(9) -.0027(8) -.0031(8) -.0066(8)
C3 .0556(10) .0349(8) .0560(11) -.0006(8) -.0042(10) -.0054(8)
C4 .0541(10) .0549(11) .0552(12) .0102(9) -.0008(10) -.0073(10)
C5 .0432(10) .0602(11) .0521(11) .0012(9) .0038(9) -.0028(10)
C6 .0542(10) .0519(10) .0408(10) -.0121(9) .0020(9) .0009(9)
C7 .0425(8) .0455(9) .0347(9) .0005(7) .0022(8) -.0010(8)
C8 .0349(7) .0386(8) .0391(9) -.0038(7) -.0040(8) .0028(7)
C9 .0324(8) .0320(7) .0464(10) -.0044(7) .0008(8) .0012(7)
C10 .0350(8) .0398(8) .0471(10) -.0031(7) .0038(9) .0039(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . . 1.262(2) yes
N1 C2 . . 1.368(2) yes
N1 C6 . . 1.365(3) yes
N1 H1 . . .962(16) no
C2 C3 . . 1.409(3) yes
C3 C4 . . 1.350(3) yes
C3 H2 . . .900(15) no
C4 C5 . . 1.391(3) yes
C4 H3 . . 1.003(17) no
C5 C6 . . 1.340(3) yes
C5 H4 . . .979(16) no
C6 H5 . . .941(14) no
O2 C7 . . 1.305(2) no
O2 H10 . . 1.20(2) no
O3 C7 . . 1.216(2) no
O4 C8 . . 1.419(2) no
O4 H8 . . .80(2) no
O5 C9 . . 1.406(2) no
O5 H9 . . .95(2) no
O6 C10 . . 1.316(2) no
O6 H11 . . .842(19) no
O7 C10 . . 1.205(2) no
C7 C8 . . 1.518(3) no
C8 C9 . . 1.532(3) no
C8 H6 . . .962(15) no
C9 C10 . . 1.522(3) no
C9 H7 . . .976(12) no
O8 H12 . . .86(3) no
O8 H13 . . .798(19) no
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
C2 N1 C6 123.18(19) yes
C2 N1 H1 116.6(10) no
C6 N1 H1 120.2(10) no
O1 C2 N1 119.92(18) yes
O1 C2 C3 124.78(19) yes
N1 C2 C3 115.30(18) yes
C2 C3 C4 121.5(2) yes
C2 C3 H2 115.0(10) no
C4 C3 H2 123.5(10) no
C3 C4 C5 120.8(2) yes
C3 C4 H3 118.4(11) no
C5 C4 H3 120.9(11) no
C4 C5 C6 118.4(2) yes
C4 C5 H4 122.7(10) no
C6 C5 H4 118.6(10) no
N1 C6 C5 120.8(2) yes
N1 C6 H5 115.5(9) no
C5 C6 H5 123.7(9) no
C7 O2 H10 114.5(9) no
C8 O4 H8 106.7(15) no
C9 O5 H9 112.1(17) no
C10 O6 H11 111.1(14) no
O2 C7 O3 125.19(18) no
O2 C7 C8 111.66(17) no
O3 C7 C8 123.15(17) no
O4 C8 C7 109.27(16) no
O4 C8 C9 109.09(15) no
O4 C8 H6 112.8(9) no
C7 C8 C9 108.33(16) no
C7 C8 H6 108.4(9) no
C9 C8 H6 108.8(9) no
O5 C9 C8 111.36(15) no
O5 C9 C10 110.93(16) no
O5 C9 H7 109.4(8) no
C8 C9 C10 111.46(16) no
C8 C9 H7 108.0(8) no
C10 C9 H7 105.4(8) no
O6 C10 O7 125.02(18) no
O6 C10 C9 111.38(17) no
O7 C10 C9 123.57(19) no
H12 O8 H13 105(2) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
C9 O1 3.255(2) 2_565 no
H7 O1 2.563(13) 2_565 no
O3 C4 3.186(3) 2_664 no
O1 C6 3.373(3) 2_665 no
N1 C6 3.280(3) 2_665 no
C2 C6 3.302(3) 2_665 no
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
_geom_torsion_publ_flag
O1 C2 N1 C6 180.0(2) no
O1 C2 C3 C4 179.6(2) no
N1 C2 C3 C4 .2(4) no
N1 C6 C5 C4 .5(4) no
C2 N1 C6 C5 .2(4) no
C2 C3 C4 C5 .5(4) no
C3 C2 N1 C6 -.6(3) no
C3 C4 C5 C6 -.8(4) no
C7 C8 C9 C10 -170.56(15) no
O2 C7 C8 O4 -174.75(17) no
O2 C7 C8 C9 66.5(2) no
O3 C7 C8 O4 5.8(3) no
O3 C7 C8 C9 -112.9(2) no
O4 C8 C9 O5 -53.87(19) no
O4 C8 C9 C10 70.59(19) no
O5 C9 C8 C7 65.0(2) no
O5 C9 C10 O6 -174.34(15) no
O5 C9 C10 O7 3.6(3) no
O6 C10 C9 C8 61.0(2) no
O7 C10 C9 C8 -121.1(2) no
_cod_database_fobs_code 2011939