#------------------------------------------------------------------------------
#$Date: 2018-06-14 15:53:24 +0300 (Thu, 14 Jun 2018) $
#$Revision: 208377 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/45/2004576.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_2004576
loop_
_publ_author_name
'Okabe, N.'
'Miura, J.'
'Shimosaki, A.'
_publ_section_title
;
 Xanthurenic Acid Monohydrate
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              663
_journal_page_last               665
_journal_paper_doi               10.1107/S0108270195013072
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac          'C10 H7 N1 O4, H2 O1'
_chemical_formula_moiety         C9H4(OH)2NH^+^CO2^-^(H2O)
_chemical_formula_sum            'C10 H9 N O5'
_chemical_formula_weight         223.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90
_cell_angle_beta                 106.92(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.710(5)
_cell_length_b                   12.354(2)
_cell_length_c                   10.920(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      19.35
_cell_measurement_theta_min      15.45
_cell_volume                     995.1(7)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1988)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1985)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_structure_refinement  TEXSAN
_computing_structure_solution
'SHELX86 (Sheldrick, 1985) and DIRDIF (Beurskens, 1984)'
_diffrn_measurement_device       'Rigaku AFC-5R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2565
_diffrn_reflns_theta_max         27.50
_diffrn_standards_decay_%        0.30
_diffrn_standards_interval_count 150
_diffrn_standards_interval_time  80
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.42
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   2.64
_refine_ls_hydrogen_treatment    'H atom parameters not refined'
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1473
_refine_ls_R_factor_obs          0.072
_refine_ls_shift/esd_max         0.018
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 4Fₒ²/σ²(Fₒ²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.087
_reflns_number_observed          1473
_reflns_number_total             2397
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            as1218.cif
_cod_data_source_block           xanth
_cod_depositor_comments
;
 Updating space group information and adding the symmetry operation list.

 Antanas Vaitkus,
 2018-06-15

 Marking attached hydrogen atoms.

 Antanas Vaitkus,
 2017-03-24

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_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C10 H9 N1 O5'
_cod_database_code               2004576
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
_atom_site_attached_hydrogens
O(1) -.0327(4) .7532(3) -0.1460(3) 4.40(10) 0
O(2) .0415(4) .8318(2) .0473(3) 3.70(10) 0
O(3) .2427(4) .0145(3) 1.0093(3) 4.7(2) 2
O(4) .4092(3) .5304(2) .3200(2) 3.20(10) 0
O(8) .1496(4) .4297(2) -0.2373(2) 3.50(10) 0
N(1) .1521(4) .5774(3) -.0566(3) 2.30(10) 0
C(2) .1454(4) .6538(3) .0287(3) 2.30(10) 0
C(3) .2292(5) .6401(3) .1554(4) 2.60(10) 0
C(4) .3316(5) .5454(3) .2026(3) 2.40(10) 0
C(5) .4403(5) .3685(3) .1409(4) 3.0(2) 0
C(6) .4396(5) .2930(3) .0488(4) 3.3(2) 0
C(7) .3427(6) .3109(3) -.0787(4) 3.4(2) 0
C(8) .2463(5) .4056(3) -0.1154(4) 2.6(2) 0
C(9) .2480(5) .4834(3) -.0212(3) 2.20(10) 0
C(10) .3432(5) .4662(3) .1079(3) 2.30(10) 0
C(11) .0415(5) .7550(3) -.0279(4) 2.9(2) 0
H(1) .0954 .5952 -0.1380 2.0 0
H(3) .2134 .6997 .2052 3.1 0
H(4) .3291 .5380 .3902 3.9 0
H(5) .5028 .3514 .2195 2.9 0
H(6) .5388 .2255 .0839 3.8 0
H(7) .3365 .2658 -0.1547 4.0 0
H(8) .1971 .4549 -0.3044 4.2 0
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(9) 121.9(3) yes
N(1) C(2) C(3) 121.3(3) yes
N(1) C(2) C(11) 114.9(3) yes
C(3) C(2) C(11) 123.8(3) yes
C(2) C(3) C(4) 121.5(3) yes
O(4) C(4) C(3) 122.6(4) yes
O(4) C(4) C(10) 121.2(3) yes
C(3) C(4) C(10) 116.2(3) yes
C(6) C(5) C(10) 120.4(4) yes
C(5) C(6) C(7) 120.8(4) yes
C(6) C(7) C(8) 120.7(4) yes
O(8) C(8) C(7) 124.5(4) yes
O(8) C(8) C(9) 117.0(3) yes
C(7) C(8) C(9) 118.5(4) yes
N(1) C(9) C(8) 119.0(3) yes
N(1) C(9) C(10) 119.6(3) yes
C(8) C(9) C(10) 121.5(3) yes
C(4) C(10) C(5) 122.4(3) yes
C(4) C(10) C(9) 119.5(3) yes
C(5) C(10) C(9) 118.0(3) yes
O(1) C(11) O(2) 127.0(4) yes
O(1) C(11) C(2) 115.7(4) yes
O(2) C(11) C(2) 117.2(3) yes
C(4) O(4) H(4) 119.37 no
C(8) O(8) H(8) 126.63 no
C(2) N(1) H(1) 114.30 no
C(9) N(1) H(1) 123.69 no
C(2) C(3) H(3) 112.78 no
C(4) C(3) H(3) 125.74 no
C(6) C(5) H(5) 115.88 no
C(10) C(5) H(5) 123.67 no
C(5) C(6) H(6) 113.54 no
C(7) C(6) H(6) 124.98 no
C(6) C(7) H(7) 129.09 no
C(8) C(7) H(7) 110.08 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(11) 1.250(5) yes
O(2) C(11) 1.254(5) yes
O(4) C(4) 1.261(4) yes
O(8) C(8) 1.356(5) yes
N(1) C(2) 1.337(5) yes
N(1) C(9) 1.370(4) yes
C(2) C(3) 1.356(5) yes
C(2) C(11) 1.517(5) yes
C(3) C(4) 1.421(5) yes
C(4) C(10) 1.446(5) yes
C(5) C(6) 1.370(6) yes
C(5) C(10) 1.410(5) yes
C(6) C(7) 1.393(6) yes
C(7) C(8) 1.382(6) yes
C(8) C(9) 1.405(5) yes
C(9) C(10) 1.403(5) yes
O(4) H(4) 1.119 no
O(8) H(8) 0.962 no
N(1) H(1) 0.896 no
C(3) H(3) 0.944 no
C(5) H(5) 0.880 no
C(6) H(6) 1.121 no
C(7) H(7) 0.989 no
