#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/82/2228286.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228286
loop_
_publ_author_name
'Jia, Jing-Jing'
'Meng, Xiu-Jin'
'Liang, Shi-Zhang'
'Zhang, Shu-Hua'
'Jiang, Yi-Min'
_publ_section_title
;
 Piperazine-2,3,5,6-tetraone
;
_journal_coeditor_code           DN2617
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3315
_journal_paper_doi               10.1107/S1600536810048075
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C4 H2 N2 O4'
_chemical_formula_moiety         'C4 H2 N2 O4'
_chemical_formula_sum            'C4 H2 N2 O4'
_chemical_formula_weight         142.08
_chemical_name_systematic
;
Piperazine-2,3,5,6-tetraone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 105.25(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.1630(10)
_cell_length_b                   8.6220(17)
_cell_length_c                   5.6540(11)
_cell_measurement_reflns_used    438
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      4.42
_cell_volume                     242.83(9)
_computing_cell_refinement       'XSCANS (Siemens, 1994)'
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        'XSCANS (Siemens, 1994)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and
PLATON (Spek, 2009)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            1357
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         4.42
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.9779
_exptl_absorpt_correction_T_min  0.9299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.943
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             144
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.225
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     46
_refine_ls_number_reflns         438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.225
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0477
_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)+(0.0355P)²+0.1147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0922
_reflns_number_gt                383
_reflns_number_total             438
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2617.cif
_cod_data_source_block           I
_cod_original_cell_volume        242.83(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228286
_cod_database_fobs_code          2228286
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
O O1 0.1613(3) 0.55814(19) 0.7646(3) 0.0343(5) Uani d . 1 . .
O O2 0.8069(3) 0.25100(19) 0.6060(3) 0.0342(5) Uani d . 1 . .
N N1 0.4775(4) 0.3995(2) 0.6856(3) 0.0261(5) Uani d . 1 . .
H H1 0.4603 0.3362 0.7981 0.031 Uiso calc R 1 . .
C C1 0.6621(5) 0.3635(2) 0.5614(4) 0.0233(5) Uani d . 1 . .
C C2 0.3169(4) 0.5281(2) 0.6461(4) 0.0233(5) Uani d . 1 . .
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 0.0357(10) 0.0355(10) 0.0373(10) 0.0010(8) 0.0197(9) -0.0034(8)
O2 0.0348(10) 0.0268(9) 0.0402(10) 0.0099(8) 0.0086(8) 0.0048(7)
N1 0.0330(11) 0.0229(10) 0.0248(11) 0.0004(9) 0.0120(9) 0.0053(8)
C1 0.0221(12) 0.0205(11) 0.0256(12) -0.0019(10) 0.0034(10) -0.0017(9)
C2 0.0224(12) 0.0225(11) 0.0239(12) -0.0027(10) 0.0042(10) -0.0038(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 N1 C2 . . 125.31(19) ?
C1 N1 H1 . . 117.3 ?
C2 N1 H1 . . 117.3 ?
O2 C1 N1 . . 123.6(2) ?
O2 C1 C2 . 3_666 119.10(19) ?
N1 C1 C2 . 3_666 117.28(19) ?
O1 C2 N1 . . 123.3(2) ?
O1 C2 C1 . 3_666 119.3(2) ?
N1 C2 C1 . 3_666 117.35(18) ?
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 C2 . 1.202(3) ?
O2 C1 . 1.210(3) ?
N1 C1 . 1.360(3) ?
N1 C2 . 1.368(3) ?
N1 H1 . 0.8600 ?
C1 C2 3_666 1.526(3) ?
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 O1 2_546 0.86 2.48 3.060(2) 125.4
N1 H1 O2 4_566 0.86 2.23 3.035(2) 157.0
