#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/47/2014742.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_2014742
loop_
_publ_author_name
'Sarangarajan, Thanjavur Ramabhadran'
'Panchanatheswaran, Krishnaswamy '
'Low, John N.'
'Glidewell, Christopher'
_publ_section_title
;
 Piperazine-2,5-dione--oxalic acid--water (1/1/2) and a redetermination
 of piperazine-2,5-dione, both at 120K: hydrogen-bonded sheets
 containing multiple ring types
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o118
_journal_page_last               o121
_journal_paper_doi               10.1107/S0108270104034055
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C4 H6 N2 O2'
_chemical_formula_moiety         'C4 H6 N2 O2'
_chemical_formula_sum            'C4 H6 N2 O2'
_chemical_formula_weight         114.11
_chemical_name_systematic
;
2,5-Piperazinedione
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 96.46(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.8967(10)
_cell_length_b                   11.527(3)
_cell_length_c                   5.159(2)
_cell_measurement_reflns_used    508
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      4.35
_cell_volume                     230.26(12)
_computing_cell_refinement       'DENZO--SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'program (reference)?'
_computing_data_reduction        DENZO--SMN
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'OSCAIL and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'OSCAIL (McArdle , 2003) and SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1053
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2525
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         4.35
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             120
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.489
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.245
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     37
_refine_ls_number_reflns         508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.245
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0670
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1311P)²+0.0775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2049
_refine_ls_wR_factor_ref         0.2060
_reflns_number_gt                490
_reflns_number_total             508
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1802.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014742
_cod_database_fobs_code          2014742
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
O2 0.5941(4) 0.63335(11) 0.6680(2) 0.0190(6) Uani d . 1 . . O
N1 0.8110(4) 0.45696(13) 0.7787(3) 0.0159(6) Uani d . 1 . . N
C2 0.7821(4) 0.56985(18) 0.8176(3) 0.0148(6) Uani d . 1 . . C
C3 0.9821(5) 0.62391(14) 1.0532(4) 0.0159(7) Uani d . 1 . . C
H1 0.6939 0.4281 0.6376 0.019 Uiso calc R 1 . . H
H3A 1.1366 0.6842 0.9939 0.019 Uiso calc R 1 . . H
H3B 0.8175 0.6631 1.1572 0.019 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
O2 0.0226(10) 0.0126(9) 0.0206(9) 0.0006(5) -0.0028(6) 0.0012(5)
N1 0.0191(11) 0.0114(10) 0.0165(9) 0.0000(6) -0.0010(7) -0.0005(5)
C2 0.0158(11) 0.0122(10) 0.0169(10) -0.0012(6) 0.0042(7) 0.0017(6)
C3 0.0168(11) 0.0107(10) 0.0198(11) 0.0014(6) -0.0001(7) 0.0001(6)
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
C2 N1 C3 . 3_767 126.23(15) no
C2 N1 H1 . . 116.9 no
C3 N1 H1 3_767 . 116.9 no
O2 C2 N1 . . 122.68(17) no
O2 C2 C3 . . 118.31(17) no
N1 C2 C3 . . 119.01(16) no
N1 C3 C2 3_767 . 114.75(15) no
N1 C3 H3A 3_767 . 108.6 no
C2 C3 H3A . . 108.6 no
N1 C3 H3B 3_767 . 108.6 no
C2 C3 H3B . . 108.6 no
H3A C3 H3B . . 107.6 no
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 . 1.323(3) no
N1 C3 3_767 1.454(2) no
N1 H1 . 0.88 no
C2 O2 . 1.241(2) no
C2 C3 . 1.503(3) no
C3 H3A . 0.99 no
C3 H3B . 0.99 no
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
_geom_hbond_publ_flag
N1 H1 O2 3_666 0.88 1.96 2.840(2) 176 y
C3 H3B O2 4_565 0.99 2.51 3.266(3) 133 y
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_1
_geom_torsion_site_symmetry_4
_geom_torsion
C3 N1 C2 O2 3_767 . -178.40(14)
C3 N1 C2 C3 3_767 . 1.1(3)
O2 C2 C3 N1 . 3_767 178.55(13)
N1 C2 C3 N1 . 3_767 -1.0(3)
