#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/19/2011936.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_2011936
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_paper_doi               10.1107/S0108270101002839
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         '2C5 H5 N O , C2 H2 O4'
_chemical_formula_structural     '2C5 H5 N O , C2 H2 O4'
_chemical_formula_sum            'C12 H12 N2 O6'
_chemical_formula_weight         280.24
_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_type_scat_source           IntTabC
_cell_angle_alpha                98.86(4)
_cell_angle_beta                 97.66(3)
_cell_angle_gamma                109.61(3)
_cell_formula_units_Z            1
_cell_length_a                   9.162(3)
_cell_length_b                   9.898(3)
_cell_length_c                   3.7672(17)
_cell_measurement_reflns_used    18
_cell_measurement_temperature    298
_cell_measurement_theta_max      11.5
_cell_measurement_theta_min      9.4
_cell_volume                     311.6(2)
_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      298
_diffrn_measurement_device       'Rigaku AFC-5R'
_diffrn_measurement_method       ω/2θ
_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  .006
_diffrn_reflns_av_sigmaI/netI    .016
_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       4
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1645
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.2
_diffrn_standards_decay_%        <0.9
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             146
_exptl_crystal_size_max          .50
_exptl_crystal_size_mid          .38
_exptl_crystal_size_min          .35
_refine_diff_density_max         .24
_refine_diff_density_min         -.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.96
_refine_ls_goodness_of_fit_ref   1.98
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .060
_refine_ls_R_factor_gt           .059
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00031|Fo|²]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         .100
_refine_ls_wR_factor_ref         .098
_reflns_number_gt                1336
_reflns_number_total             1428
_reflns_threshold_expression     I>0.1σ(I)
_cod_data_source_file            bk1582.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_formula_sum        'C12 H12 N2 O6 '
_cod_database_code               2011936
loop_
_symmetry_equiv_pos_as_xyz
'  +x,  +y,  +z'
'  -x,  -y,  -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 .80311(7) .41104(7) .0347(2) .04484(18) Uani d ? . 1.000
O2 .56467(8) .19067(7) .0910(2) .0542(2) Uani d ? . 1.000
O3 .67367(8) .04132(7) -.1697(2) .0561(2) Uani d ? . 1.000
N1 .95991(8) .64707(8) .2854(2) .03573(19) Uani d ? . 1.000
C2 .81684(9) .53621(9) .2102(2) .0324(2) Uani d ? . 1.000
C3 .69251(10) .57249(10) .3352(3) .0394(2) Uani d ? . 1.000
C4 .71801(12) .71081(11) .5140(3) .0428(3) Uani d ? . 1.000
C5 .86907(12) .82065(10) .5837(3) .0443(3) Uani d ? . 1.000
C6 .98733(11) .78527(10) .4669(3) .0427(3) Uani d ? . 1.000
C7 .57155(9) .06303(9) -.0288(3) .0370(2) Uani d ? . 1.000
H1 1.0371(15) .6232(12) .194(3) .053(3) Uiso d ? . 1.000
H2 .5883(14) .4935(12) .284(3) .051(3) Uiso d ? . 1.000
H3 .6346(15) .7365(13) .596(3) .060(3) Uiso d ? . 1.000
H4 .8863(13) .9167(13) .716(3) .057(3) Uiso d ? . 1.000
H5 1.0942(15) .8534(12) .501(3) .059(3) Uiso d ? . 1.000
H6 .6554(18) .2687(17) .058(4) .084(4) 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 .0383(3) .0275(3) .0682(4) .0092(3) .0244(3) .0033(3)
O2 .0458(4) .0289(3) .0893(6) .0096(3) .0380(4) .0050(3)
O3 .0412(4) .0401(4) .0894(6) .0118(3) .0376(4) .0060(4)
N1 .0302(4) .0318(4) .0476(4) .0124(3) .0140(3) .0077(3)
C2 .0312(4) .0304(4) .0389(5) .0120(3) .0129(3) .0098(3)
C3 .0320(4) .0397(5) .0499(5) .0129(4) .0184(4) .0104(4)
C4 .0463(5) .0464(5) .0479(5) .0260(4) .0227(4) .0130(4)
C5 .0545(6) .0334(5) .0480(5) .0187(4) .0174(4) .0045(4)
C6 .0382(5) .0330(5) .0534(6) .0089(4) .0121(4) .0062(4)
C7 .0309(4) .0316(4) .0469(5) .0095(3) .0143(4) .0026(4)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C6 . 123.88(11) yes
C2 N1 H1 . 114.7(10) no
C6 N1 H1 . 121.3(10) no
O1 C2 N1 . 118.99(10) yes
O1 C2 C3 . 125.19(11) yes
N1 C2 C3 . 115.81(11) yes
C2 C3 C4 . 120.89(12) yes
C2 C3 H2 . 116.9(9) no
C4 C3 H2 . 122.2(9) no
C3 C4 C5 . 120.49(12) yes
C3 C4 H3 . 121.4(11) no
C5 C4 H3 . 118.1(11) no
C4 C5 C6 . 118.39(12) yes
C4 C5 H4 . 119.7(10) no
C6 C5 H4 . 121.8(10) no
N1 C6 C5 . 120.53(12) yes
N1 C6 H5 . 115.3(10) no
C5 C6 H5 . 124.1(10) no
C7 O2 H6 . 111.1(12) no
O2 C7 O3 . 125.93(11) no
O2 C7 C7 2_655 111.68(12) no
O3 C7 C7 2_655 122.39(14) no
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 . . 1.2683(15) yes
N1 C2 . . 1.3573(16) yes
N1 C6 . . 1.3554(17) yes
N1 H1 . . .908(19) no
C2 C3 . . 1.4191(16) yes
C3 C4 . . 1.3573(19) yes
C3 H2 . . .981(16) no
C4 C5 . . 1.404(2) yes
C4 H3 . . .955(18) no
C5 C6 . . 1.3507(19) yes
C5 H4 . . .953(16) no
C6 H5 . . .963(17) no
O2 C7 . . 1.2996(15) no
O2 H6 . . .96(2) no
O3 C7 . . 1.1983(15) no
C7 C7 . 2_655 1.544(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
O3 C7 3.302(2) 2_654 no
O3 C7 3.307(2) 1_554 no
O3 C5 3.3588(19) 1_544 no
O3 H4 2.679(17) 1_544 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_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C2 N1 C6 . . 179.19(12) no
O1 C2 C3 C4 . . -178.48(12) no
N1 C2 C3 C4 . . .81(19) no
N1 C6 C5 C4 . . .3(2) no
C2 N1 C6 C5 . . -.4(2) no
C2 C3 C4 C5 . . -.9(2) no
C3 C2 N1 C6 . . -.15(18) no
C3 C4 C5 C6 . . .3(2) no
O2 C7 C7 O3 2_655 2_655 -.4(3) no
