#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2224288.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_2224288
loop_
_publ_author_name
'Arman, Hadi D.'
'Poplaukhin, Pavel'
'Tiekink, Edward R. T.'
_publ_section_title
;
 2-Pyridone: monoclinic polymorph
;
_journal_coeditor_code           HG2602
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3187
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C5 H5 N1 O1'
_chemical_formula_moiety         'C5 H5 N1 O1'
_chemical_formula_sum            'C5 H5 N O'
_chemical_formula_weight         95.10
_chemical_name_systematic
;
2-pyridone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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
_cell_angle_beta                 92.242(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.2027(13)
_cell_length_b                   16.327(4)
_cell_length_c                   9.1046(18)
_cell_measurement_reflns_used    3046
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      3.3
_cell_volume                     921.3(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      98(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku AFC12\K/SATURN724'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_av_sigmaI/netI    0.033
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6582
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.10
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.10
_refine_ls_R_factor_all          0.049
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0583P)^2^+0.2750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.113
_refine_ls_wR_factor_ref         0.117
_reflns_number_gt                1724
_reflns_number_total             1903
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    hg2602.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_[local]_cod_chemical_formula_sum_orig 'C5 H5 N1 O1'
_cod_database_code               2224288
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O O1 0.27541(14) 0.36020(6) 0.47704(10) 0.0239(2) Uani d . 1
N N1 -0.07408(17) 0.31779(7) 0.48531(12) 0.0201(3) Uani d . 1
H H1N -0.1007 0.3587 0.5450 0.024 Uiso calc R 1
C C1 0.1321(2) 0.30993(8) 0.43716(14) 0.0195(3) Uani d . 1
C C2 -0.2397(2) 0.26660(8) 0.44686(15) 0.0232(3) Uani d . 1
H H2 -0.3795 0.2769 0.4819 0.028 Uiso calc R 1
C C3 -0.2074(2) 0.20065(8) 0.35857(15) 0.0236(3) Uani d . 1
H H3 -0.3219 0.1641 0.3330 0.028 Uiso calc R 1
C C4 0.0019(2) 0.18832(8) 0.30615(14) 0.0224(3) Uani d . 1
H H4 0.0289 0.1426 0.2450 0.027 Uiso calc R 1
C C5 0.1649(2) 0.24113(8) 0.34226(14) 0.0209(3) Uani d . 1
H H5 0.3033 0.2324 0.3039 0.025 Uiso calc R 1
O O2 -0.14759(15) 0.44304(6) 0.67815(11) 0.0263(3) Uani d . 1
N N2 0.19925(17) 0.48837(7) 0.67120(12) 0.0204(3) Uani d . 1
H H2N 0.2238 0.4519 0.6027 0.024 Uiso calc R 1
C C6 -0.0049(2) 0.49182(8) 0.72495(14) 0.0199(3) Uani d . 1
C C7 -0.0344(2) 0.55309(8) 0.83511(15) 0.0236(3) Uani d . 1
H H7 -0.1717 0.5592 0.8765 0.028 Uiso calc R 1
C C8 0.1311(2) 0.60263(9) 0.88132(16) 0.0267(3) Uani d . 1
H H8 0.1078 0.6427 0.9547 0.032 Uiso calc R 1
C C9 0.3370(2) 0.59536(9) 0.82168(17) 0.0276(3) Uani d . 1
H H9 0.4526 0.6299 0.8539 0.033 Uiso calc R 1
C C10 0.3652(2) 0.53746(9) 0.71679(15) 0.0243(3) Uani d . 1
H H10 0.5022 0.5313 0.6751 0.029 Uiso calc R 1
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 0.0186(5) 0.0256(5) 0.0277(5) -0.0021(4) 0.0025(4) -0.0048(4)
N1 0.0186(6) 0.0198(5) 0.0219(5) 0.0010(4) 0.0027(4) -0.0035(4)
C1 0.0180(6) 0.0210(6) 0.0195(6) 0.0012(5) 0.0000(5) 0.0018(5)
C2 0.0178(6) 0.0248(7) 0.0272(7) -0.0013(5) 0.0026(5) -0.0022(5)
C3 0.0208(7) 0.0220(7) 0.0281(7) -0.0021(5) 0.0013(5) -0.0036(5)
C4 0.0244(7) 0.0202(6) 0.0227(6) 0.0036(5) -0.0004(5) -0.0025(5)
C5 0.0179(6) 0.0239(7) 0.0211(6) 0.0031(5) 0.0031(5) -0.0010(5)
O2 0.0206(5) 0.0245(5) 0.0342(5) -0.0041(4) 0.0062(4) -0.0078(4)
N2 0.0209(6) 0.0183(5) 0.0221(5) -0.0003(4) 0.0029(4) -0.0014(4)
C6 0.0191(6) 0.0183(6) 0.0222(6) 0.0011(5) 0.0009(5) 0.0029(5)
C7 0.0212(6) 0.0252(7) 0.0245(7) 0.0031(5) 0.0025(5) -0.0007(5)
C8 0.0268(7) 0.0262(7) 0.0270(7) 0.0035(5) -0.0010(6) -0.0063(5)
C9 0.0227(7) 0.0256(7) 0.0342(8) -0.0026(5) -0.0024(6) -0.0043(6)
C10 0.0176(6) 0.0251(7) 0.0304(7) -0.0016(5) 0.0015(5) 0.0016(6)
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'
N N 0.0061 0.0033 '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 N1 C1 124.33(11)
C2 N1 H1N 117.8
C1 N1 H1N 117.8
O1 C1 N1 120.32(11)
O1 C1 C5 124.83(12)
N1 C1 C5 114.84(11)
N1 C2 C3 120.67(12)
N1 C2 H2 119.7
C3 C2 H2 119.7
C2 C3 C4 118.00(12)
C2 C3 H3 121.0
C4 C3 H3 121.0
C5 C4 C3 120.77(12)
C5 C4 H4 119.6
C3 C4 H4 119.6
C4 C5 C1 121.36(12)
C4 C5 H5 119.3
C1 C5 H5 119.3
C10 N2 C6 124.37(11)
C10 N2 H2N 117.8
C6 N2 H2N 117.8
O2 C6 N2 120.04(12)
O2 C6 C7 124.99(12)
N2 C6 C7 114.96(11)
C8 C7 C6 121.03(12)
C8 C7 H7 119.5
C6 C7 H7 119.5
C7 C8 C9 120.93(13)
C7 C8 H8 119.5
C9 C8 H8 119.5
C10 C9 C8 118.12(13)
C10 C9 H9 120.9
C8 C9 H9 120.9
N2 C10 C9 120.59(12)
N2 C10 H10 119.7
C9 C10 H10 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2529(16)
N1 C2 1.3597(17)
N1 C1 1.3743(17)
N1 H1N 0.8800
C1 C5 1.4365(18)
C2 C3 1.3633(19)
C2 H2 0.9500
C3 C4 1.4151(18)
C3 H3 0.9500
C4 C5 1.3590(19)
C4 H4 0.9500
C5 H5 0.9500
O2 C6 1.2530(16)
N2 C10 1.3567(17)
N2 C6 1.3762(17)
N2 H2N 0.8800
C6 C7 1.4335(18)
C7 C8 1.3607(19)
C7 H7 0.9500
C8 C9 1.412(2)
C8 H8 0.9500
C9 C10 1.360(2)
C9 H9 0.9500
C10 H10 0.9500
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
N1 H1n O2 1_555 0.88 1.86 2.7450(16) 177
N2 H2n O1 1_555 0.88 1.92 2.7915(16) 171
C2 H2 O1 1_455 0.95 2.53 3.3943(18) 150
C4 H4 O2 4_665 0.95 2.54 3.2989(18) 137
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
C2 N1 C1 O1 179.47(12)
C2 N1 C1 C5 -1.04(18)
C1 N1 C2 C3 2.1(2)
N1 C2 C3 C4 -1.3(2)
C2 C3 C4 C5 -0.4(2)
C3 C4 C5 C1 1.5(2)
O1 C1 C5 C4 178.72(12)
N1 C1 C5 C4 -0.74(18)
C10 N2 C6 O2 -178.77(12)
C10 N2 C6 C7 0.61(18)
O2 C6 C7 C8 178.83(13)
N2 C6 C7 C8 -0.51(19)
C6 C7 C8 C9 0.2(2)
C7 C8 C9 C10 0.0(2)
C6 N2 C10 C9 -0.4(2)
C8 C9 C10 N2 0.1(2)