#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/70/2227006.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_2227006
loop_
_publ_author_name
'Liu, Ling-Li'
_publ_section_title
;
 Piperazine-1,4-diium 2-(carboxymethyl)-2-hydroxybutanedioate
 monohydrate
;
_journal_coeditor_code           LH5096
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2191
_journal_paper_doi               10.1107/S1600536810030151
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C4 H12 N2 2+, C6 H6 O7 2-, H2 O'
_chemical_formula_moiety         'C4 H12 N2 2+, C6 H6 O7 2-, H2 O'
_chemical_formula_sum            'C10 H20 N2 O8'
_chemical_formula_weight         296.28
_chemical_name_systematic
;
Piperazine-1,4-diium 2-(carboxymethyl)-2-hydroxybutanedioate monohydrate
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 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                 112.047(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2055(12)
_cell_length_b                   6.8314(9)
_cell_length_c                   11.2443(14)
_cell_measurement_reflns_used    3551
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.39
_cell_volume                     655.41(15)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick,2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick,2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '0.3° wide ω exposures'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed Siemens Mo tube'
_diffrn_radiation_type           'Mo k\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4284
_diffrn_reflns_theta_full        28.24
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9871
_exptl_absorpt_correction_T_min  0.9644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.492
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.843
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         1605
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      0.839
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0447
_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)+(0.1299P)²+0.0532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1243
_reflns_number_gt                1597
_reflns_number_total             1605
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5096.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               2227006
_cod_database_fobs_code          2227006
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, 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
C C1 -0.0340(3) 0.4003(3) -0.1528(2) 0.0297(4) Uani d . 1 . .
H H1C -0.0235 0.4467 -0.2307 0.036 Uiso calc R 1 . .
H H1D -0.0636 0.5106 -0.1124 0.036 Uiso calc R 1 . .
C C2 -0.1605(3) 0.2459(4) -0.1861(3) 0.0332(5) Uani d . 1 . .
H H2C -0.1796 0.2105 -0.1097 0.040 Uiso calc R 1 . .
H H2D -0.2570 0.2982 -0.2484 0.040 Uiso calc R 1 . .
C C3 0.0376(3) -0.0130(3) -0.1483(2) 0.0305(5) Uani d . 1 . .
H H3A 0.0673 -0.1265 -0.1859 0.037 Uiso calc R 1 . .
H H3B 0.0251 -0.0540 -0.0701 0.037 Uiso calc R 1 . .
C C4 0.1648(3) 0.1419(4) -0.1174(2) 0.0303(5) Uani d . 1 . .
H H4A 0.2618 0.0903 -0.0553 0.036 Uiso calc R 1 . .
H H4B 0.1826 0.1754 -0.1946 0.036 Uiso calc R 1 . .
C C5 0.0510(2) 0.2958(3) 0.2147(2) 0.0246(4) Uani d . 1 . .
C C6 0.0104(3) 0.2231(3) 0.3269(2) 0.0265(4) Uani d . 1 . .
H H6A 0.0993 0.1501 0.3846 0.032 Uiso calc R 1 . .
H H6B -0.0768 0.1325 0.2937 0.032 Uiso calc R 1 . .
C C7 -0.0330(2) 0.3809(3) 0.40527(19) 0.0199(4) Uani d . 1 . .
C C8 0.1144(3) 0.4982(3) 0.4852(2) 0.0262(4) Uani d . 1 . .
H H8A 0.1838 0.4157 0.5529 0.031 Uiso calc R 1 . .
H H8B 0.1697 0.5375 0.4307 0.031 Uiso calc R 1 . .
C C9 0.0719(3) 0.6782(3) 0.5437(2) 0.0252(4) Uani d . 1 . .
C C10 -0.0977(2) 0.2788(3) 0.49726(19) 0.0214(4) Uani d . 1 . .
N N1 0.1189(2) 0.3207(3) -0.06442(18) 0.0258(4) Uani d D 1 . .
H H1A 0.194(3) 0.403(4) -0.044(4) 0.031 Uiso d D 1 . .
H H1B 0.121(4) 0.286(5) 0.010(2) 0.031 Uiso d D 1 . .
N N2 -0.1133(2) 0.0681(3) -0.23994(18) 0.0265(4) Uani d D 1 . .
H H2A -0.094(4) 0.085(6) -0.308(3) 0.032 Uiso d D 1 . .
H H2B -0.183(4) -0.019(4) -0.248(4) 0.032 Uiso d D 1 . .
O O1 0.1237(2) 0.1775(3) 0.17088(18) 0.0372(5) Uani d . 1 . .
O O2 0.0071(3) 0.4609(3) 0.1684(2) 0.0461(6) Uani d . 1 . .
O O3 -0.1506(2) 0.5083(3) 0.32461(16) 0.0297(4) Uani d D 1 . .
H H3C -0.122(5) 0.535(7) 0.261(4) 0.045 Uiso d D 1 . .
O O4 -0.2272(2) 0.3241(2) 0.49788(19) 0.0315(4) Uani d . 1 . .
O O5 -0.0096(2) 0.1479(3) 0.56970(16) 0.0303(4) Uani d . 1 . .
O O6 0.1374(3) 0.8387(3) 0.5218(2) 0.0423(5) Uani d D 1 . .
H H6C 0.102(6) 0.942(6) 0.547(5) 0.063 Uiso d D 1 . .
O O7 -0.0127(3) 0.6765(3) 0.60374(19) 0.0368(4) Uani d . 1 . .
O O8 -0.0953(5) 0.8366(6) 0.0753(6) 0.0923(14) Uani d D 1 . .
H H8C -0.032(9) 0.739(7) 0.107(10) 0.139 Uiso d D 1 . .
H H8D -0.039(10) 0.938(7) 0.114(9) 0.139 Uiso d 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
N1 C1 C2 . . 110.99(19) ?
N1 C1 H1C . . 109.4 ?
C2 C1 H1C . . 109.4 ?
N1 C1 H1D . . 109.4 ?
C2 C1 H1D . . 109.4 ?
H1C C1 H1D . . 108.0 ?
N2 C2 C1 . . 110.75(19) ?
N2 C2 H2C . . 109.5 ?
C1 C2 H2C . . 109.5 ?
N2 C2 H2D . . 109.5 ?
C1 C2 H2D . . 109.5 ?
H2C C2 H2D . . 108.1 ?
N2 C3 C4 . . 109.71(19) ?
N2 C3 H3A . . 109.7 ?
C4 C3 H3A . . 109.7 ?
N2 C3 H3B . . 109.7 ?
C4 C3 H3B . . 109.7 ?
H3A C3 H3B . . 108.2 ?
N1 C4 C3 . . 110.68(19) ?
N1 C4 H4A . . 109.5 ?
C3 C4 H4A . . 109.5 ?
N1 C4 H4B . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 108.1 ?
O2 C5 O1 . . 123.7(2) ?
O2 C5 C6 . . 119.9(2) ?
O1 C5 C6 . . 116.4(2) ?
C5 C6 C7 . . 116.23(18) ?
C5 C6 H6A . . 108.2 ?
C7 C6 H6A . . 108.2 ?
C5 C6 H6B . . 108.2 ?
C7 C6 H6B . . 108.2 ?
H6A C6 H6B . . 107.4 ?
O3 C7 C6 . . 111.33(17) ?
O3 C7 C10 . . 108.20(17) ?
C6 C7 C10 . . 108.45(16) ?
O3 C7 C8 . . 110.29(17) ?
C6 C7 C8 . . 109.76(16) ?
C10 C7 C8 . . 108.75(16) ?
C9 C8 C7 . . 111.19(18) ?
C9 C8 H8A . . 109.4 ?
C7 C8 H8A . . 109.4 ?
C9 C8 H8B . . 109.4 ?
C7 C8 H8B . . 109.4 ?
H8A C8 H8B . . 108.0 ?
O7 C9 O6 . . 123.3(2) ?
O7 C9 C8 . . 124.2(2) ?
O6 C9 C8 . . 112.56(19) ?
O4 C10 O5 . . 123.8(2) ?
O4 C10 C7 . . 120.53(19) ?
O5 C10 C7 . . 115.69(18) ?
C4 N1 C1 . . 111.87(18) ?
C4 N1 H1A . . 109(2) ?
C1 N1 H1A . . 114(2) ?
C4 N1 H1B . . 105(2) ?
C1 N1 H1B . . 115(2) ?
H1A N1 H1B . . 102(4) ?
C3 N2 C2 . . 111.07(18) ?
C3 N2 H2A . . 103(2) ?
C2 N2 H2A . . 116(3) ?
C3 N2 H2B . . 107(3) ?
C2 N2 H2B . . 107(3) ?
H2A N2 H2B . . 113(4) ?
C7 O3 H3C . . 105(3) ?
C9 O6 H6C . . 111(4) ?
H8C O8 H8D . . 103(5) ?
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
C1 N1 . 1.488(3) ?
C1 C2 . 1.510(3) ?
C1 H1C . 0.9700 ?
C1 H1D . 0.9700 ?
C2 N2 . 1.492(3) ?
C2 H2C . 0.9700 ?
C2 H2D . 0.9700 ?
C3 N2 . 1.491(3) ?
C3 C4 . 1.519(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 N1 . 1.488(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 O2 . 1.244(3) ?
C5 O1 . 1.262(3) ?
C5 C6 . 1.527(3) ?
C6 C7 . 1.537(3) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 O3 . 1.420(2) ?
C7 C10 . 1.540(3) ?
C7 C8 . 1.541(3) ?
C8 C9 . 1.514(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 O7 . 1.207(3) ?
C9 O6 . 1.318(3) ?
C10 O4 . 1.235(3) ?
C10 O5 . 1.274(3) ?
N1 H1A . 0.85(2) ?
N1 H1B . 0.86(2) ?
N2 H2A . 0.86(2) ?
N2 H2B . 0.86(2) ?
O3 H3C . 0.87(3) ?
O6 H6C . 0.87(3) ?
O8 H8C . 0.87(8) ?
O8 H8D . 0.87(8) ?
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 H1A O3 2_564 0.85(2) 2.48(3) 3.068(3) 126(3) yes
N1 H1A O4 2_564 0.85(2) 1.99(3) 2.764(3) 150(3) yes
N1 H1B O1 . 0.86(2) 1.95(2) 2.806(3) 174(4) yes
N2 H2A O5 1_554 0.86(2) 1.86(2) 2.706(2) 167(4) yes
N2 H2B O1 2_454 0.86(2) 1.99(2) 2.804(3) 159(4) yes
O3 H3C O2 . 0.87(3) 1.92(4) 2.685(3) 147(4) yes
O6 H6C O5 1_565 0.87(3) 1.82(3) 2.671(3) 167(5) yes
O8 H8C O2 . 0.87(8) 2.00(4) 2.798(4) 151(8) yes
O8 H8D O1 1_565 0.87(8) 2.15(4) 3.003(5) 165(10) yes
C1 H1C O7 1_554 0.97 2.47 3.391(3) 159.4 yes
C3 H3A O7 1_544 0.97 2.58 3.394(3) 141.9 yes
C3 H3B O8 1_545 0.97 2.41 3.344(7) 160.9 yes
C4 H4B O5 1_554 0.97 2.58 3.274(3) 128.4 yes
C6 H6A O6 1_545 0.97 2.57 3.338(3) 135.8 yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 N2 . . . . -55.1(3) ?
N2 C3 C4 N1 . . . . 57.1(3) ?
O2 C5 C6 C7 . . . . -20.1(3) ?
O1 C5 C6 C7 . . . . 162.6(2) ?
C5 C6 C7 O3 . . . . 51.2(3) ?
C5 C6 C7 C10 . . . . 170.11(18) ?
C5 C6 C7 C8 . . . . -71.2(2) ?
O3 C7 C8 C9 . . . . 46.2(2) ?
C6 C7 C8 C9 . . . . 169.19(18) ?
C10 C7 C8 C9 . . . . -72.3(2) ?
C7 C8 C9 O7 . . . . 50.3(3) ?
C7 C8 C9 O6 . . . . -129.7(2) ?
O3 C7 C10 O4 . . . . -4.9(3) ?
C6 C7 C10 O4 . . . . -125.8(2) ?
C8 C7 C10 O4 . . . . 114.9(2) ?
O3 C7 C10 O5 . . . . 174.87(17) ?
C6 C7 C10 O5 . . . . 54.0(2) ?
C8 C7 C10 O5 . . . . -65.3(2) ?
C3 C4 N1 C1 . . . . -56.1(2) ?
C2 C1 N1 C4 . . . . 55.0(2) ?
C4 C3 N2 C2 . . . . -58.1(2) ?
C1 C2 N2 C3 . . . . 57.4(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 19978517
2 PubChem 139079378
