#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/00/2010020.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_2010020
loop_
_publ_author_name
'Orvig, C.'
'Rettig, S.J.'
'Zhang, Z.'
_publ_section_title
;
 1-Carboxymethyl-3-hydroxy-2-methyl-4(1H)-pyridinone (monoclinic
 form 2)
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1511
_journal_page_last               1514
_journal_paper_doi               10.1107/S0108270194000508
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C8 H9 N O4'
_chemical_formula_weight         183.16
_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_type_scat_source           IntTabIV
_cell_angle_alpha                90
_cell_angle_beta                 102.780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3800(10)
_cell_length_b                   10.474(4)
_cell_length_c                   9.554(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294
_cell_measurement_theta_max      21.9
_cell_measurement_theta_min      18.9
_cell_volume                     817.8(4)
_diffrn_measurement_device       'Rigaku AFC6S'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2658
_diffrn_reflns_theta_max         30
_diffrn_standards_decay_%        insignificant
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   'empirical (T values are relative)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       Prism
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.15
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   2.85
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1492
_refine_ls_R_factor_obs          0.043
_refine_ls_shift/esd_max         0.02
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=4Fₒ²/σ²(Fₒ²)
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.041
_reflns_number_observed          1492
_reflns_number_total             2380
_reflns_observed_criterion       I>=3\s(I)
_cod_data_source_file            cd1062.cif
_cod_data_source_block           cd1062_structure_1_of_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w=4F~o~^2^/\s^2^(F~o~^2^)' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=4F~o~^2^/\s^2^(F~o~^2^)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        817.8(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C8 H9 N1 O4'
_cod_database_code               2010020
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,1/2-y,1/2+z
-x,-1/2+y,-1/2-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O(1) -.0809(2) .03150(10) .27900(10)
O(2) -.22410(10) .16790(10) .04060(10)
O(3) .67750(10) .17620(10) .33530(10)
O(4) .4438(2) .28210(10) .3122(2)
N(1) .2688(2) .10630(10) .1354(2)
C(1) .2554(3) -.0105(2) .3573(3)
C(2) .1764(2) .0612(2) .2256(2)
C(3) .0092(2) .0823(2) .1917(2)
C(4) -.0639(2) .1513(2) .0681(2)
C(5) .0364(2) .1958(2) -.0190(2)
C(6) .1994(2) .1722(2) .0154(2)
C(7) .4479(2) .0942(2) .1705(2)
C(8) .5259(2) .1937(2) .2821(2)
H(1) -.180(3) .078(2) .277(3)
H(2) -.268(3) .230(3) -.047(3)
H(3) .177(3) -.027(2) .408(3)
H(4) .353(3) .032(3) .414(3)
H(5) .296(3) -.096(3) .331(3)
H(6) -.012(2) .240(2) -.103(2)
H(7) .273(2) .203(2) -.047(2)
H(8) .479(2) .007(2) .205(2)
H(9) .489(2) .108(2) .081(2)
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
C(2) N(1) C(6) 120.90(10) yes
C(2) N(1) C(7) 121.4(2) yes
C(6) N(1) C(7) 117.6(2) yes
N(1) C(2) C(1) 120.0(2) yes
N(1) C(2) C(3) 118.9(2) yes
C(1) C(2) C(3) 121.1(2) yes
O(1) C(3) C(2) 117.8(2) yes
O(1) C(3) C(4) 121.50(10) yes
C(2) C(3) C(4) 120.6(2) yes
O(2) C(4) C(3) 118.0(2) yes
O(2) C(4) C(5) 124.1(2) yes
C(3) C(4) C(5) 117.9(2) yes
C(4) C(5) C(6) 120.4(2) yes
N(1) C(6) C(5) 121.3(2) yes
N(1) C(7) C(8) 111.00(10) yes
O(3) C(8) O(4) 125.3(2) yes
O(3) C(8) C(7) 114.5(2) yes
O(4) C(8) C(7) 120.2(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(3) 1.352(2) yes
O(2) C(4) 1.321(2) yes
O(3) C(8) 1.273(2) yes
O(4) C(8) 1.226(2) yes
N(1) C(2) 1.364(2) yes
N(1) C(6) 1.355(2) yes
N(1) C(7) 1.469(2) yes
C(1) C(2) 1.489(3) yes
C(2) C(3) 1.384(2) yes
C(3) C(4) 1.404(2) yes
C(4) C(5) 1.387(3) yes
C(5) C(6) 1.355(3) yes
C(7) C(8) 1.529(3) yes
O(1) H(1) 0.96(2) no
O(2) H(2) 1.05(3) no
C(1) H(3) 0.91(2) no
C(1) H(4) 0.98(3) no
C(1) H(5) 1.01(3) no
C(5) H(6) 0.94(2) no
C(6) H(7) 1.00(2) no
C(7) H(8) 0.99(2) no
C(7) H(9) 1.00(2) 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
O(1) C(3) C(2) N(1) 176.90(10) no
O(1) C(3) C(2) C(1) -2.5(3) no
O(1) C(3) C(4) O(2) 1.5(2) no
O(1) C(3) C(4) C(5) -177.3(2) no
O(2) C(4) C(3) C(2) 179.6(2) no
O(2) C(4) C(5) C(6) -178.6(2) no
O(2) C(4) C(5) H(6) -1.0(10) no
O(3) C(8) C(7) N(1) 169.0(2) no
O(3) C(8) C(7) H(8) 47.0(10) no
O(3) C(8) C(7) H(9) -71.0(10) no
O(4) C(8) C(7) N(1) -12.0(3) no
O(4) C(8) C(7) H(8) -134.0(10) no
O(4) C(8) C(7) H(9) 108.0(10) no
N(1) C(2) C(1) H(3) 175(2) no
N(1) C(2) C(1) H(4) 48(2) no
N(1) C(2) C(1) H(5) -69(2) no
N(1) C(2) C(3) C(4) -1.3(3) no
N(1) C(6) C(5) C(4) -0.6(3) no
N(1) C(6) C(5) H(6) -179.0(10) no
C(1) C(2) N(1) C(6) -179.7(2) no
C(1) C(2) N(1) C(7) -4.7(3) no
C(1) C(2) C(3) C(4) 179.3(2) no
C(2) N(1) C(6) C(5) 0.1(3) no
C(2) N(1) C(6) H(7) 180.0(10) no
C(2) N(1) C(7) C(8) -77.3(2) no
C(2) N(1) C(7) H(8) 45.0(10) no
C(2) N(1) C(7) H(9) 163.0(10) no
C(2) C(3) O(1) H(1) 154(2) no
C(2) C(3) C(4) C(5) 0.8(3) no
C(3) C(2) N(1) C(6) 0.8(3) no
C(3) C(2) N(1) C(7) 175.9(2) no
C(3) C(2) C(1) H(3) -5(2) no
C(3) C(2) C(1) H(4) -132(2) no
C(3) C(2) C(1) H(5) 111(2) no
C(3) C(4) O(2) H(2) 173(2) no
C(3) C(4) C(5) C(6) 0.2(3) no
C(3) C(4) C(5) H(6) 178.0(10) no
C(4) C(3) O(1) H(1) -28(2) no
C(4) C(5) C(6) H(7) 180.0(10) no
C(5) C(4) O(2) H(2) -8(2) no
C(5) C(6) N(1) C(7) -175.1(2) no
C(6) N(1) C(7) C(8) 98.0(2) no
C(6) N(1) C(7) H(8) -139.0(10) no
C(6) N(1) C(7) H(9) -22.0(10) no
C(7) N(1) C(6) H(7) 5.0(10) no
H(6) C(5) C(6) H(7) 2(2) no
