#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/42/2204264.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_2204264
loop_
_publ_author_name
'Thomas C. Lewis'
'Derek A. Tocher'
_publ_section_title
;
 5,5-Dihydroxybarbituric acid monohydrate (alloxan dihydrate)
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1689
_journal_page_last               o1690
_journal_paper_doi               10.1107/S1600536804021555
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C4 H4 N2 O5, H2 O1'
_chemical_formula_moiety         'C4 H4 N2 O5, H2 O1'
_chemical_formula_sum            'C4 H6 N2 O6'
_chemical_formula_weight         178.11
_chemical_name_systematic
;
5,5-dihydroxybarbituric acid monohydrate
;
_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_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                105.401(3)
_cell_angle_beta                 93.134(3)
_cell_angle_gamma                115.089(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6730(11)
_cell_length_b                   7.5834(13)
_cell_length_c                   7.6157(13)
_cell_measurement_reflns_used    712
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      2.83
_cell_volume                     330.26(10)
_computing_cell_refinement       SAINT
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'ω rotation scans with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2972
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.83
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.9615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             184
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.236
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0502P)²+0.0119P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1021
_reflns_number_gt                1274
_reflns_number_total             1536
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6506.cif
_cod_data_source_block           I
_cod_database_code               2204264
_cod_database_fobs_code          2204264
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_occupancy
_atom_site_type_symbol
O2 0.2526(2) 0.32902(18) 0.90727(17) 0.0200(3) Uani d 1 O
O4 0.6356(2) 0.34785(19) 0.43384(16) 0.0214(3) Uani d 1 O
O6 0.7119(2) 0.02976(19) 0.86645(17) 0.0207(3) Uani d 1 O
O7 0.9445(2) 0.42247(18) 0.76705(17) 0.0194(3) Uani d 1 O
O8 0.7906(2) 0.09757(19) 0.54162(17) 0.0204(3) Uani d 1 O
O1W 0.0411(3) 0.1981(2) 0.2940(2) 0.0339(4) Uani d 1 O
N1 0.4853(2) 0.1829(2) 0.8839(2) 0.0160(3) Uani d 1 N
N3 0.4626(2) 0.3615(2) 0.6818(2) 0.0171(3) Uani d 1 N
C2 0.3919(3) 0.2946(2) 0.8279(2) 0.0156(4) Uani d 1 C
C4 0.6073(3) 0.3162(2) 0.5801(2) 0.0160(4) Uani d 1 C
C5 0.7514(3) 0.2387(2) 0.6700(2) 0.0155(4) Uani d 1 C
C6 0.6456(3) 0.1366(2) 0.8121(2) 0.0154(3) Uani d 1 C
H1 0.421(4) 0.128(3) 0.969(3) 0.033(6) Uiso d 1 H
H3 0.398(4) 0.416(3) 0.641(3) 0.035(6) Uiso d 1 H
H7 1.035(4) 0.383(4) 0.813(3) 0.046(7) Uiso d 1 H
H8 0.859(4) 0.149(3) 0.472(3) 0.034(6) Uiso d 1 H
H1W 0.107(5) 0.117(4) 0.244(4) 0.059(8) Uiso d 1 H
H2W 0.030(5) 0.268(4) 0.232(4) 0.072(10) Uiso d 1 H
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
O2 0.0185(6) 0.0251(7) 0.0231(7) 0.0143(5) 0.0074(5) 0.0101(5)
O4 0.0264(7) 0.0273(7) 0.0190(7) 0.0157(6) 0.0081(5) 0.0136(5)
O6 0.0236(7) 0.0270(7) 0.0256(7) 0.0179(6) 0.0120(5) 0.0175(5)
O7 0.0158(6) 0.0205(7) 0.0262(7) 0.0093(5) 0.0038(5) 0.0121(5)
O8 0.0292(7) 0.0213(7) 0.0204(7) 0.0161(6) 0.0143(5) 0.0116(5)
O1W 0.0465(9) 0.0343(8) 0.0412(9) 0.0277(8) 0.0276(8) 0.0235(7)
N1 0.0171(7) 0.0204(7) 0.0173(7) 0.0110(6) 0.0068(6) 0.0116(6)
N3 0.0198(7) 0.0201(7) 0.0191(7) 0.0133(6) 0.0049(6) 0.0106(6)
C2 0.0155(8) 0.0151(8) 0.0173(8) 0.0079(7) 0.0019(6) 0.0056(7)
C4 0.0171(8) 0.0128(8) 0.0192(8) 0.0068(7) 0.0033(6) 0.0068(6)
C5 0.0162(8) 0.0170(8) 0.0172(8) 0.0090(7) 0.0054(6) 0.0084(7)
C6 0.0144(8) 0.0155(8) 0.0186(9) 0.0075(7) 0.0038(6) 0.0077(7)
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
C5 O7 H7 104.6(16)
C5 O8 H8 109.7(16)
H1W O1W H2W 115(3)
C6 N1 C2 126.62(15)
C6 N1 H1 119.2(13)
C2 N1 H1 113.9(13)
C4 N3 C2 125.45(14)
C4 N3 H3 116.6(15)
C2 N3 H3 117.1(16)
O2 C2 N3 123.04(15)
O2 C2 N1 119.95(15)
N3 C2 N1 117.00(15)
O4 C4 N3 123.23(15)
O4 C4 C5 120.38(15)
N3 C4 C5 116.18(14)
O8 C5 O7 115.10(14)
O8 C5 C6 106.53(13)
O7 C5 C6 107.51(13)
O8 C5 C4 112.19(14)
O7 C5 C4 102.10(12)
C6 C5 C4 113.50(13)
O6 C6 N1 121.83(15)
O6 C6 C5 121.52(14)
N1 C6 C5 116.49(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C2 1.2171(19)
O4 C4 1.209(2)
O6 C6 1.2188(19)
O7 C5 1.405(2)
O7 H7 0.87(2)
O8 C5 1.3706(19)
O8 H8 0.80(2)
O1W H1W 0.92(3)
O1W H2W 0.82(3)
N1 C6 1.360(2)
N1 C2 1.378(2)
N1 H1 0.89(2)
N3 C4 1.368(2)
N3 C2 1.368(2)
N3 H3 0.81(2)
C4 C5 1.536(2)
C5 C6 1.527(2)
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 H1 O6 2_657 0.89(2) 1.95(2) 2.8366(18) 170.7(19)
N3 H3 O4 2_666 0.81(2) 2.11(2) 2.8736(18) 157(2)
O7 H7 O2 1_655 0.87(2) 1.83(3) 2.6958(17) 173(2)
O8 H8 O1W 1_655 0.80(2) 1.87(2) 2.6380(19) 161(2)
O1W H1W O6 2_656 0.92(3) 2.04(3) 2.9516(19) 173(2)
O1W H2W O7 2_666 0.82(3) 2.28(3) 2.9973(19) 147(3)
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
C4 N3 C2 O2 -175.55(16)
C4 N3 C2 N1 4.2(2)
C6 N1 C2 O2 -178.33(16)
C6 N1 C2 N3 1.9(2)
C2 N3 C4 O4 166.85(16)
C2 N3 C4 C5 -18.4(2)
O4 C4 C5 O8 -38.9(2)
N3 C4 C5 O8 146.15(14)
O4 C4 C5 O7 84.86(18)
N3 C4 C5 O7 -90.07(16)
O4 C4 C5 C6 -159.76(15)
N3 C4 C5 C6 25.3(2)
C2 N1 C6 O6 -177.16(16)
C2 N1 C6 C5 7.3(2)
O8 C5 C6 O6 40.3(2)
O7 C5 C6 O6 -83.59(19)
C4 C5 C6 O6 164.28(15)
O8 C5 C6 N1 -144.19(14)
O7 C5 C6 N1 91.92(17)
C4 C5 C6 N1 -20.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130455
