#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/35/2013568.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_2013568
loop_
_publ_author_name
'Ramos Silva, Manuela'
'Matos Beja, Ana'
'Paixao, Jose Antonio'
'Sobral, Abilio J. F. N.'
'Cabral, Lucia M. L.'
'Rocha Gonsalves, A. M. dA.'
_publ_section_title
;
 R_4^4(30) rectangular rings in
 2,5-dioxopiperazine-1,4-diacetic acid
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o562
_journal_page_last               o563
_journal_paper_doi               10.1107/S0108270103017803
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C8 H10 N2 O6'
_chemical_formula_moiety         'C8 H10 N2 O6'
_chemical_formula_sum            'C8 H10 N2 O6'
_chemical_formula_weight         230.18
_chemical_name_systematic
;
2,5-dioxopiperazine-1,4-diacetic acid
;
_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_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.189(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.5322(6)
_cell_length_b                   9.1505(13)
_cell_length_c                   9.8235(8)
_cell_measurement_reflns_used    14
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.64
_cell_measurement_theta_min      7.73
_cell_volume                     472.44(9)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4 diffractometer'
_diffrn_measurement_method       'profile data from ω-2θ scans'
_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  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2943
_diffrn_reflns_theta_full        25.48
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_min         3.12
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  180
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0421
_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)+(0.0482P)²+0.2592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1168
_reflns_number_gt                604
_reflns_number_total             872
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa1026.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2013568
_cod_database_fobs_code          2013568
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 -0.3192(4) -0.2214(2) -0.28891(19) 0.0692(7) Uani d . 1 . . O
O2 -0.3017(4) -0.1464(2) -0.50026(18) 0.0611(6) Uani d . 1 . . O
H2 -0.411(7) -0.221(4) -0.528(3) 0.092 Uiso d . 1 . . H
O3 0.3075(3) -0.16118(19) -0.10313(17) 0.0487(5) Uani d . 1 . . O
N1 -0.0172(3) -0.00327(19) -0.14474(18) 0.0347(5) Uani d . 1 . . N
C1 -0.2441(5) -0.1380(3) -0.3599(2) 0.0430(6) Uani d . 1 . . C
C2 -0.0649(5) -0.0134(3) -0.2987(2) 0.0400(6) Uani d . 1 . . C
H2A 0.0944 -0.0289 -0.3184 0.048 Uiso calc R 1 . . H
H2B -0.1385 0.0774 -0.3439 0.048 Uiso calc R 1 . . H
C3 0.1656(4) -0.0844(2) -0.0576(2) 0.0352(5) Uani d . 1 . . C
C4 -0.2048(4) 0.0785(2) -0.0999(2) 0.0387(6) Uani d . 1 . . C
H4A -0.3709 0.0361 -0.1464 0.046 Uiso calc R 1 . . H
H4B -0.2082 0.1779 -0.1347 0.046 Uiso calc R 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
O1 0.0841(15) 0.0716(13) 0.0492(11) -0.0344(12) 0.0168(10) -0.0023(9)
O2 0.0741(14) 0.0711(13) 0.0358(10) -0.0218(11) 0.0138(9) -0.0109(9)
O3 0.0485(10) 0.0551(11) 0.0444(10) 0.0151(8) 0.0174(8) -0.0037(8)
N1 0.0354(10) 0.0372(10) 0.0316(10) 0.0023(8) 0.0106(7) -0.0007(7)
C1 0.0447(14) 0.0467(14) 0.0369(13) 0.0005(11) 0.0120(11) -0.0042(11)
C2 0.0454(14) 0.0420(13) 0.0335(12) -0.0010(10) 0.0136(10) 0.0015(9)
C3 0.0350(12) 0.0328(12) 0.0375(12) -0.0032(10) 0.0108(10) -0.0022(9)
C4 0.0373(13) 0.0399(13) 0.0378(12) 0.0052(10) 0.0102(10) 0.0005(9)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O2 H2 . . 106(2) ?
C3 N1 C2 . . 119.23(19) ?
C3 N1 C4 . . 124.31(18) yes
C2 N1 C4 . . 115.65(17) yes
O1 C1 O2 . . 124.1(2) yes
O1 C1 C2 . . 123.8(2) ?
O2 C1 C2 . . 112.1(2) ?
N1 C2 C1 . . 110.26(18) yes
N1 C2 H2A . . 109.6 ?
C1 C2 H2A . . 109.6 ?
N1 C2 H2B . . 109.6 ?
C1 C2 H2B . . 109.6 ?
H2A C2 H2B . . 108.1 ?
O3 C3 N1 . . 121.7(2) ?
O3 C3 C4 . 3 119.4(2) ?
N1 C3 C4 . 3 118.8(2) ?
N1 C4 C3 . 3 116.46(18) ?
N1 C4 H4A . . 108.2 ?
C3 C4 H4A 3 . 108.2 ?
N1 C4 H4B . . 108.2 ?
C3 C4 H4B 3 . 108.2 ?
H4A C4 H4B . . 107.3 ?
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
O1 C1 . 1.192(3) yes
O2 C1 . 1.317(3) yes
O2 H2 . 0.89(4) yes
O3 C3 . 1.236(3) yes
N1 C3 . 1.329(3) yes
N1 C2 . 1.455(3) yes
C1 C2 . 1.507(3) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 3 1.495(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
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
O2 H2 O3 4_455 0.89(4) 1.85(4) 2.726(3) 166(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_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 C2 C1 . 85.7(3) yes
C4 N1 C2 C1 . -84.4(2) ?
O1 C1 C2 N1 . -5.0(4) yes
O2 C1 C2 N1 . 176.95(19) yes
C2 N1 C3 O3 . 4.8(3) yes
C4 N1 C3 O3 . 174.0(2) yes
C2 N1 C3 C4 3 -177.1(2) ?
C4 N1 C3 C4 3 -7.9(4) ?
C3 N1 C4 C3 3 7.7(4) ?
C2 N1 C4 C3 3 177.29(19) ?
