#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/92/2209295.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_2209295
loop_
_publ_author_name
'Churakov, Andrei V.'
'Kuz'mina, Lyudmila G.'
'Prikhodchenko, Petr V.'
'Howard, Judith A. K.'
_publ_section_title
;
 The first molecular structure containing four hydroperoxo groups:
 piperazine-2,3,5,6-tetrayl tetrahydroperoxide pyrazine disolvate
 dihydrate
;
_journal_coeditor_code           RZ2031
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2265
_journal_page_last               o2267
_journal_paper_doi               10.1107/S1600536806016485
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C4 H10 N2 O8, 2C4 H4 N2, 2H2 O'
_chemical_formula_moiety         'C4 H10 N2 O8, 2C4 H4 N2, 2H2 O'
_chemical_formula_sum            'C12 H22 N6 O10'
_chemical_formula_weight         410.36
_chemical_name_systematic
;
piperazine-2,3,5,6-tetrayl tetrahydroperoxide pyrazine disolvate dihydrate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.729(3)
_cell_angle_beta                 95.974(4)
_cell_angle_gamma                91.417(3)
_cell_formula_units_Z            1
_cell_length_a                   6.1538(6)
_cell_length_b                   7.3047(8)
_cell_length_c                   10.3364(12)
_cell_measurement_reflns_used    1131
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.458
_cell_measurement_theta_min      2.816
_cell_volume                     457.56(9)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL-Plus (Bruker, 2000)'
_computing_publication_material  SHELXTL-Plus
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker SMART 6K'
_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  0.0118
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2645
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.9683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0372
_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)+(0.0248P)²+0.2345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0898
_reflns_number_gt                1710
_reflns_number_total             2162
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2031.cif
_cod_data_source_block           I
_cod_database_code               2209295
_cod_database_fobs_code          2209295
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
N N1 1.1231(2) 0.79178(18) 0.50775(13) 0.0261(3) Uani d 1
N N2 0.7499(2) 0.63944(18) 0.35086(14) 0.0290(3) Uani d 1
C C1 0.9426(3) 0.7464(2) 0.55999(16) 0.0281(3) Uani d 1
C C2 0.7583(3) 0.6716(2) 0.48149(18) 0.0299(4) Uani d 1
C C3 1.1158(3) 0.7607(2) 0.37735(15) 0.0256(3) Uani d 1
C C4 0.9304(3) 0.6850(2) 0.29966(16) 0.0272(3) Uani d 1
N N3 0.32175(19) 0.87876(16) 0.97556(12) 0.0182(3) Uani d 1
C C5 0.3104(2) 1.03857(19) 1.07043(14) 0.0176(3) Uani d 1
C C6 0.4605(2) 0.88510(19) 0.87366(14) 0.0182(3) Uani d 1
O O1 0.36537(16) 1.00211(14) 0.78281(10) 0.0218(2) Uani d 1
O O2 0.19076(15) 1.17748(13) 1.00797(10) 0.0200(2) Uani d 1
O O3 0.11802(16) 1.30694(14) 1.11516(11) 0.0228(2) Uani d 1
O O4 0.47963(18) 0.96406(16) 0.66468(11) 0.0265(3) Uani d 1
O O5 0.4042(2) 0.58225(17) 0.14218(13) 0.0325(3) Uani d 1
H H1 0.940(3) 0.768(3) 0.651(2) 0.033(5) Uiso d 1
H H2 0.628(3) 0.643(3) 0.519(2) 0.040(5) Uiso d 1
H H3 1.240(3) 0.794(2) 0.3417(18) 0.027(5) Uiso d 1
H H4 0.929(3) 0.668(2) 0.2075(19) 0.029(5) Uiso d 1
H H51 0.508(4) 0.600(4) 0.209(3) 0.068(8) Uiso d 1
H H52 0.412(4) 0.661(4) 0.088(3) 0.061(7) Uiso d 1
H H5 0.230(3) 1.008(2) 1.1425(16) 0.017(4) Uiso d 1
H H6 0.469(2) 0.764(2) 0.8258(15) 0.012(4) Uiso d 1
H H32 0.202(3) 0.826(3) 0.9490(18) 0.026(5) Uiso d 1
H H31 0.211(3) 1.400(3) 1.1126(19) 0.034(5) Uiso d 1
H H41 0.369(3) 0.907(3) 0.612(2) 0.034 Uiso d 1
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
C3 N1 C1 . . 116.91(14)
C4 N2 C2 . . 116.13(14)
N1 C1 C2 . . 121.06(15)
N1 C1 H1 . . 119.6(12)
C2 C1 H1 . . 119.4(12)
N2 C2 C1 . . 122.40(15)
N2 C2 H2 . . 116.8(13)
C1 C2 H2 . . 120.8(13)
N1 C3 C4 . . 121.54(15)
N1 C3 H3 . . 116.6(12)
C4 C3 H3 . . 121.9(12)
N2 C4 C3 . . 121.95(15)
N2 C4 H4 . . 118.5(11)
C3 C4 H4 . . 119.5(11)
C5 N3 C6 . . 119.31(11)
C5 N3 H32 . . 113.8(12)
C6 N3 H32 . . 112.9(12)
N3 C5 O2 . . 108.69(11)
N3 C5 C6 . 2_677 110.81(11)
O2 C5 C6 . 2_677 110.11(11)
N3 C5 H5 . . 110.3(10)
O2 C5 H5 . . 107.5(9)
C6 C5 H5 2_677 . 109.3(10)
N3 C6 O1 . . 108.62(11)
N3 C6 C5 . 2_677 111.10(12)
O1 C6 C5 . 2_677 109.50(11)
N3 C6 H6 . . 110.2(9)
O1 C6 H6 . . 107.5(9)
C5 C6 H6 2_677 . 109.8(9)
C6 O1 O4 . . 105.82(9)
C5 O2 O3 . . 106.00(9)
O2 O3 H31 . . 98.2(12)
O1 O4 H41 . . 97.7(12)
H51 O5 H52 . . 113(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C3 . 1.332(2)
N1 C1 . 1.338(2)
N2 C4 . 1.333(2)
N2 C2 . 1.334(2)
C1 C2 . 1.379(2)
C1 H1 . 0.932(19)
C2 H2 . 0.95(2)
C3 C4 . 1.382(2)
C3 H3 . 0.924(18)
C4 H4 . 0.943(19)
N3 C5 . 1.4281(18)
N3 C6 . 1.4279(18)
N3 H32 . 0.83(2)
C5 O2 . 1.4502(16)
C5 C6 2_677 1.5286(19)
C5 H5 . 0.984(16)
C6 O1 . 1.4427(17)
C6 C5 2_677 1.5286(19)
C6 H6 . 0.958(16)
O1 O4 . 1.4695(14)
O2 O3 . 1.4713(14)
O3 H31 . 0.88(2)
O4 H41 . 0.88(2)
O5 H51 . 0.88(3)
O5 H52 . 0.86(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
O4 H41 N1 1_455 0.88(2) 1.88(2) 2.7573(18) 176.2(18)
O3 H31 O5 1_566 0.88(2) 1.74(2) 2.6068(16) 168.2(19)
N3 H32 O3 2_577 0.83(2) 2.17(2) 2.9985(16) 178.1(17)
O5 H51 N2 . 0.88(3) 1.97(3) 2.8483(19) 177(2)
O5 H52 N3 1_554 0.86(3) 2.14(3) 2.9648(18) 160(2)
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 C1 C2 . . -0.2(2)
C4 N2 C2 C1 . . -0.5(2)
N1 C1 C2 N2 . . 0.5(3)
C1 N1 C3 C4 . . 0.0(2)
C2 N2 C4 C3 . . 0.2(2)
N1 C3 C4 N2 . . 0.0(2)
C6 N3 C5 O2 . . 72.06(15)
C6 N3 C5 C6 . 2_677 -49.07(18)
C5 N3 C6 O1 . . -71.31(15)
C5 N3 C6 C5 . 2_677 49.20(18)
N3 C6 O1 O4 . . -165.20(10)
C5 C6 O1 O4 2_677 . 73.31(12)
N3 C5 O2 O3 . . 160.69(10)
C6 C5 O2 O3 2_677 . -77.76(12)
