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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/58/7225858.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.
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data_7225858
loop_
_publ_author_name
'Fonari, Marina S.'
'Antal, Sofia'
'Castañeda, Raúl'
'Ordonez, Carlos'
'Timofeeva, Tatiana V.'
_publ_section_title
;
 Crystalline products of CO2capture by piperazine aqueous solutions
;
_journal_issue                   33
_journal_name_full               CrystEngComm
_journal_page_first              6282
_journal_paper_doi               10.1039/C6CE01083K
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C5 H10 N2 O2, 3(H2 O)'
_chemical_formula_sum            'C5 H16 N2 O5'
_chemical_formula_weight         184.20
_chemical_name_common            'piperazinium carbaxamide trihydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-04-12 deposited with the CCDC.
2016-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.214(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.163(2)
_cell_length_b                   18.627(5)
_cell_length_c                   5.9869(17)
_cell_measurement_reflns_used    2981
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.64
_cell_measurement_theta_min      3.84
_cell_volume                     854.3(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4516
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.187
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0508 before and 0.0345 after correction.
The Ratio of minimum to maximum transmission is 0.9213.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 721 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1638
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0259
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0333P)²+0.3737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0636
_reflns_Friedel_coverage         0.936
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                1568
_reflns_number_total             1638
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01083k1.cif
_cod_data_source_block           PZHCOO-3H2O
_cod_depositor_comments
'Adding full bibliography for 7225856--7225859.cif.'
_cod_original_cell_volume        854.2(4)
_cod_database_code               7225858
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.3482(2) 0.15844(9) 0.1541(3) 0.0169(4) Uani 1 1 d . .
O2 O 0.1841(2) 0.15793(9) 0.3882(3) 0.0168(4) Uani 1 1 d . .
N1 N 0.3079(3) 0.26089(9) 0.3286(4) 0.0163(4) Uani 1 1 d . .
N2 N 0.2356(3) 0.41003(9) 0.2539(4) 0.0138(4) Uani 1 1 d . .
H1N H 0.167(4) 0.4454(17) 0.161(6) 0.026(8) Uiso 1 1 d . .
H2N H 0.332(4) 0.4341(16) 0.363(6) 0.025(8) Uiso 1 1 d . .
C1 C 0.2785(3) 0.18877(11) 0.2883(4) 0.0125(5) Uani 1 1 d . .
C2 C 0.4053(3) 0.30360(12) 0.2148(4) 0.0147(5) Uani 1 1 d . .
H2A H 0.4361 0.2742 0.1015 0.018 Uiso 1 1 calc R U
H2B H 0.5124 0.3206 0.3337 0.018 Uiso 1 1 calc R U
C3 C 0.2972(3) 0.36708(13) 0.0876(4) 0.0148(5) Uani 1 1 d . .
H3A H 0.3669 0.3973 0.0231 0.018 Uiso 1 1 calc R U
H3B H 0.1974 0.3501 -0.0439 0.018 Uiso 1 1 calc R U
C4 C 0.1397(3) 0.36467(13) 0.3742(4) 0.0155(5) Uani 1 1 d . .
H4A H 0.0315 0.3477 0.2575 0.019 Uiso 1 1 calc R U
H4B H 0.1108 0.3932 0.4910 0.019 Uiso 1 1 calc R U
C5 C 0.2505(3) 0.30107(12) 0.4959(4) 0.0146(5) Uani 1 1 d . .
H5A H 0.3515 0.3179 0.6261 0.018 Uiso 1 1 calc R U
H5B H 0.1833 0.2699 0.5615 0.018 Uiso 1 1 calc R U
O1W O 0.4871(2) 0.45733(10) 0.6680(3) 0.0170(4) Uani 1 1 d . .
H1W H 0.553(4) 0.4915(16) 0.690(5) 0.018(8) Uiso 1 1 d . .
H2W H 0.556(5) 0.4241(19) 0.735(7) 0.032(9) Uiso 1 1 d . .
O2W O 0.5014(2) 0.02970(10) 0.3418(3) 0.0170(4) Uani 1 1 d . .
H4W H 0.419(4) 0.0012(19) 0.328(6) 0.036(10) Uiso 1 1 d . .
H3W H 0.445(5) 0.074(2) 0.273(7) 0.052(12) Uiso 1 1 d . .
O3W O 0.2281(2) 0.06976(8) 0.7675(4) 0.0158(4) Uani 1 1 d . .
H5W H 0.218(6) 0.099(2) 0.654(8) 0.052(12) Uiso 1 1 d . .
H6W H 0.251(4) 0.0951(17) 0.892(7) 0.026(9) Uiso 1 1 d . .
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
C1 N1 C2 123.1(2)
C1 N1 C5 123.21(19)
C2 N1 C5 113.66(17)
C3 N2 C4 111.80(16)
O2 C1 O1 125.31(18)
O2 C1 N1 117.4(2)
O1 C1 N1 117.3(2)
N1 C2 C3 110.25(18)
N2 C3 C2 110.78(19)
N2 C4 C5 110.37(19)
N1 C5 C4 110.64(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.267(3)
O2 C1 1.265(3)
N1 C1 1.371(3)
N1 C2 1.450(3)
N1 C5 1.452(3)
N2 C3 1.494(3)
N2 C4 1.495(3)
C2 C3 1.514(3)
C4 C5 1.516(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1N O2W 0.92(3) 2.54(3) 3.098(3) 119(2) 3_455
N2 H1N O2W 0.92(3) 1.98(3) 2.783(3) 146(3) 4_454
N2 H2N O1W 0.95(3) 1.88(3) 2.760(3) 154(3) .
O1W H1W O3W 0.81(3) 1.98(3) 2.793(3) 175(3) 3
O1W H2W O2 0.84(4) 1.90(4) 2.733(3) 172(3) 4
O2W H4W O3W 0.84(3) 1.98(4) 2.814(3) 175(3) 2_554
O2W H3W O1 0.97(4) 1.79(4) 2.758(3) 177.5(17) .
O3W H5W O2 0.85(5) 1.87(5) 2.724(3) 176(4) .
O3W H6W O1 0.85(4) 1.90(4) 2.735(3) 167(3) 1_556
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202383
