#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:08:28 +0200 (vie 13 de oct de 2017) $
#$Revision: 201955 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/62/2006203.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_2006203
loop_
_publ_author_name
'Kubicki, Maciej'
'Bassyouni, Hanan A.R.'
'Codding, Penelope W.'
_publ_section_title
;
 5,7-Dichlorokynurenic Acid Hydrate, an Antagonist for the Glycine
 Binding Site on the NMDA Receptor
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              739
_journal_page_last               742
_journal_paper_doi               10.1107/S010827019700005X
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C10 H5 Cl2 N O3 , H2 O'
_chemical_formula_sum            'C10 H7 Cl2 N O4'
_chemical_formula_weight         276.07
_chemical_name_common            '5,7-dichlorokynurenic acid hydrate'
_chemical_name_systematic
;
4-oxo-1,4-dihydro-5,7-dichloroquinoline-2-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
_cell_angle_alpha                90.00
_cell_angle_beta                 93.168(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.5928(7)
_cell_length_b                   10.6943(10)
_cell_length_c                   16.0674(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      41
_cell_measurement_theta_min      14
_cell_volume                     2160.5(2)
_computing_cell_refinement       'CAD-4F software'
_computing_data_collection       'CAD-4F software'
_computing_data_reduction        'ENPROC (Rettig, 1978)'
_computing_molecular_graphics
;
Stereochemical Workstation (Siemens, 1989)
;
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'CAD-4F diffractometer'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2201
_diffrn_reflns_theta_max         74.86
_diffrn_reflns_theta_min         5.43
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  33
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.470
_exptl_absorpt_correction_T_max  0.335
_exptl_absorpt_correction_T_min  0.307
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.280
_refine_ls_extinction_coef       0.0008(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.229
_refine_ls_goodness_of_fit_obs   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.235
_refine_ls_restrained_S_obs      1.051
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_obs          .0406
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0595P)²+2.0735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1400
_refine_ls_wR_factor_obs         .1123
_reflns_number_observed          1890
_reflns_number_total             2110
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            fg1216.cif
_cod_data_source_block           mdl3
_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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0595P)^2^+2.0735P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0595P)^2^+2.0735P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value '\y-scan' was replaced with
the value 'psi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2006203
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_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
N1 .0346(10) .0516(11) .0195(9) .0022(8) .0015(8) .0023(8)
C2 .0333(12) .0407(11) .0253(11) .0006(9) .0015(9) -.0022(8)
C21 .0331(12) .0494(13) .0253(11) .0000(9) -.0009(9) -.0011(9)
O21 .0402(10) .0781(13) .0220(9) .0062(9) -.0003(7) -.0021(8)
O22 .0360(10) .0786(13) .0286(9) .0105(9) .0013(8) -.0029(8)
C3 .0314(12) .0502(13) .0261(12) .0003(9) .0038(9) -.0008(9)
C4 .0367(12) .0442(12) .0237(11) -.0011(9) .0028(9) .0011(8)
O4 .0422(10) .0878(14) .0209(9) .0085(9) .0051(7) .0073(8)
C4a .0357(12) .0335(10) .0246(11) -.0015(8) .0013(9) -.0002(8)
C5 .0387(12) .0402(12) .0252(11) .0011(9) .0000(9) .0031(8)
Cl5 .0512(4) .0714(5) .0243(4) .0106(3) -.0013(3) .0083(2)
C6 .0398(13) .0471(13) .0311(13) .0077(10) -.0020(10) .0011(9)
C7 .0367(12) .0435(12) .0299(12) .0055(9) .0045(9) -.0027(9)
Cl7 .0409(4) .0790(5) .0373(4) .0159(3) .0092(3) .0010(3)
C8 .0420(13) .0486(13) .0225(11) .0048(10) .0032(10) .0012(9)
C8a .0346(11) .0371(11) .0260(11) -.0001(9) .0009(9) .0007(8)
O1W .0372(12) .151(3) .0314(12) .0158(13) .0010(9) .0102(12)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
N1 .5593(2) .1753(2) .37938(13) .0352(5) Uani d . 1 . N
H1 .560(3) .183(3) .329(2) .041(8) Uiso d . 1 . H
C2 .4698(2) .1971(2) .41895(14) .0331(5) Uani d . 1 . C
C21 .3768(2) .2332(2) .36115(14) .0360(5) Uani d . 1 . C
O21 .3838(2) .2303(2) .28698(11) .0468(5) Uani d . 1 . O
O22 .2926(2) .2663(2) .39901(12) .0478(5) Uani d . 1 . O
H22 .243(3) .282(3) .363(3) .067(11) Uiso d . 1 . H
C3 .4659(2) .1821(2) .50240(15) .0358(5) Uani d . 1 . C
H3 .405(3) .203(3) .527(2) .051(9) Uiso d . 1 . H
C4 .5580(2) .1411(2) .55299(14) .0348(5) Uani d . 1 . C
O4 .5529(2) .1272(2) .62968(11) .0502(5) Uani d . 1 . O
C4a .6536(2) .1152(2) .50750(14) .0313(5) Uani d . 1 . C
C5 .7520(2) .0708(2) .54410(15) .0347(5) Uani d . 1 . C
Cl5 .77158(6) .04434(7) .65030(4) .0491(2) Uani d . 1 . Cl
C6 .8380(2) .0476(2) .4980(2) .0395(6) Uani d . 1 . C
H6 .907(3) .018(3) .524(2) .047 Uiso d . 1 . H
C7 .8307(2) .0701(2) .4126(2) .0366(5) Uani d . 1 . C
Cl7 .94014(6) .04237(7) .35476(4) .0521(3) Uani d . 1 . Cl
C8 .7392(2) .1133(2) .37261(15) .0376(5) Uani d . 1 . C
H8 .732(2) .129(3) .315(2) .042(7) Uiso d . 1 . H
C8a .6512(2) .1347(2) .42070(14) .0326(5) Uani d . 1 . C
O1W .1344(2) .3253(3) .30115(15) .0734(8) Uani d . 1 . O
H1W1 .131(3) .334(4) .247(3) .075(12) Uiso d . 1 . H
H1W2 .072(5) .345(4) .328(4) .109(17) Uiso d . 1 . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
_geom_angle_publ_flag
C2 N1 C8a 122.2(2) yes
C2 N1 H1 121.(2) ?
C8a N1 H1 117.(2) ?
N1 C2 C3 121.7(2) yes
N1 C2 C21 113.4(2) yes
C3 C2 C21 124.9(2) yes
O21 C21 O22 125.3(2) yes
O21 C21 C2 120.6(2) yes
O22 C21 C2 114.1(2) yes
C21 O22 H22 109.(3) ?
C2 C3 C4 121.4(2) yes
C2 C3 H3 119.(2) ?
C4 C3 H3 120.(2) ?
O4 C4 C3 120.5(2) yes
O4 C4 C4a 123.9(2) yes
C3 C4 C4a 115.6(2) yes
C8a C4a C5 115.4(2) yes
C8a C4a C4 119.4(2) yes
C5 C4a C4 125.2(2) yes
C6 C5 C4a 122.3(2) yes
C6 C5 Cl5 115.4(2) yes
C4a C5 Cl5 122.3(2) yes
C5 C6 C7 119.4(2) yes
C5 C6 H6 122.(2) ?
C7 C6 H6 119.(2) ?
C8 C7 C6 122.0(2) yes
C8 C7 Cl7 118.8(2) yes
C6 C7 Cl7 119.3(2) yes
C7 C8 C8a 117.8(2) yes
C7 C8 H8 123.4(18) ?
C8a C8 H8 118.8(18) ?
N1 C8a C8 117.1(2) yes
N1 C8a C4a 119.8(2) yes
C8 C8a C4a 123.1(2) yes
H1W1 O1W H1W2 117.(4) ?
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
N1 C2 . 1.344(3) yes
N1 C8a . 1.372(3) yes
N1 H1 . .82(3) ?
C2 C3 . 1.354(3) yes
C2 C21 . 1.504(3) yes
C21 O21 . 1.200(3) yes
C21 O22 . 1.300(3) yes
O22 H22 . .85(4) ?
C3 C4 . 1.447(3) yes
C3 H3 . .91(4) ?
C4 O4 . 1.246(3) yes
C4 C4a . 1.469(3) yes
C4a C8a . 1.409(3) yes
C4a C5 . 1.423(3) yes
C5 C6 . 1.368(4) yes
C5 Cl5 . 1.734(2) yes
C6 C7 . 1.393(4) yes
C6 H6 . .99(4) ?
C7 C8 . 1.368(4) yes
C7 Cl7 . 1.729(3) yes
C8 C8a . 1.405(3) yes
C8 H8 . .94(3) ?
O1W H1W1 . .88(5) ?
O1W H1W2 . .95(6) ?
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
C8a N1 C2 C3 1.1(4)
C8a N1 C2 C21 -176.4(2)
N1 C2 C21 O21 6.2(3)
C3 C2 C21 O21 -171.2(3)
N1 C2 C21 O22 -173.7(2)
C3 C2 C21 O22 8.9(4)
N1 C2 C3 C4 -0.3(4)
C21 C2 C3 C4 176.9(2)
C2 C3 C4 O4 -179.6(2)
C2 C3 C4 C4a -1.2(4)
O4 C4 C4a C8a -179.7(2)
C3 C4 C4a C8a 1.9(3)
O4 C4 C4a C5 0.2(4)
C3 C4 C4a C5 -178.2(2)
C8a C4a C5 C6 -0.6(3)
C4 C4a C5 C6 179.5(2)
C8a C4a C5 Cl5 178.6(2)
C4 C4a C5 Cl5 -1.4(3)
C4a C5 C6 C7 1.3(4)
Cl5 C5 C6 C7 -177.9(2)
C5 C6 C7 C8 -0.9(4)
C5 C6 C7 Cl7 179.2(2)
C6 C7 C8 C8a 0.0(4)
Cl7 C7 C8 C8a 179.8(2)
C2 N1 C8a C8 179.0(2)
C2 N1 C8a C4a -0.3(3)
C7 C8 C8a N1 -178.5(2)
C7 C8 C8a C4a 0.8(4)
C5 C4a C8a N1 178.8(2)
C4 C4a C8a N1 -1.3(3)
C5 C4a C8a C8 -0.5(3)
C4 C4a C8a C8 179.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21137704
