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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/7/22/58/7225857.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_7225857
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         'C4 H10 N2, H2 O'
_chemical_formula_sum            'C4 H12 N2 O'
_chemical_formula_weight         104.16
_chemical_name_common            'piperazine monohydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 108.778(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.856(3)
_cell_length_b                   6.681(2)
_cell_length_c                   9.172(3)
_cell_measurement_reflns_used    3311
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      4.37
_cell_volume                     571.8(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker with CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4625
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.966
_diffrn_reflns_theta_min         4.368
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       prism
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.255
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     80
_refine_ls_number_reflns         1114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0337
_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)+(0.0508P)²+0.2207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0936
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1032
_reflns_number_total             1114
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01083k1.cif
_cod_data_source_block           PZ-H2O
_cod_depositor_comments
'Adding full bibliography for 7225856--7225859.cif.'
_cod_database_code               7225857
_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.
;
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.978
_shelx_res_file
;

    mono.res created by SHELXL-2014/7


TITL mono in P2(1)/c
CELL 0.71073   9.8563   6.6806   9.1721  90.000 108.778  90.000
ZERR    4.00   0.0033   0.0022   0.0030   0.000   0.004   0.000
LATT 1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C  H  N  O
UNIT 16  48  8  4
OMIT -2 52
L.S. 4
ACTA
BOND
FMAP 2
PLAN 10
htab
HTAB O1 N1
EQIV $1 -x, -y+1, -z+1
HTAB O1 N2_$1
EQIV $2 x, -y+1/2, z-1/2
HTAB N1 O1_$2
EQIV $3 x, y+1, z
HTAB N2 O1_$3
SIZE 0.255 0.282 0.408
TEMP -0.050
WGHT    0.050800    0.220700
FVAR       1.45820
O1    4    0.223130    0.083540    0.640848    11.00000    0.01730    0.02235 =
         0.01748    0.00015    0.00707   -0.00134
H1O   2    0.268433    0.089083    0.575554    11.00000    0.04831
H2O   2    0.140796    0.148340    0.599615    11.00000    0.06327
N1    3    0.378706    0.120482    0.421866    11.00000    0.01521    0.01942 =
         0.01568    0.00507    0.00421    0.00423
H1N   2    0.334347    0.205511    0.346974    11.00000    0.02149
N2    3    0.042970    0.704296    0.525485    11.00000    0.01962    0.01149 =
         0.02002   -0.00168    0.00907   -0.00245
H2N   2    0.093987    0.799408    0.564932    11.00000    0.04186
C1    1    0.116390    0.565825    0.451357    11.00000    0.01389    0.01533 =
         0.01448    0.00125    0.00590   -0.00104
AFIX  23
H1A   2    0.197770    0.505768    0.528655    11.00000   -1.20000
H1B   2    0.151627    0.638657    0.379374    11.00000   -1.20000
AFIX   0
C2    1   -0.013425    0.597075    0.633510    11.00000    0.01582    0.01502 =
         0.01339   -0.00163    0.00549   -0.00037
AFIX  23
H2A   2   -0.062879    0.690176    0.680077    11.00000   -1.20000
H2B   2    0.065052    0.537771    0.714912    11.00000   -1.20000
AFIX   0
C3    1    0.409135   -0.066717    0.354183    11.00000    0.01625    0.02105 =
         0.01340   -0.00006    0.00378   -0.00180
AFIX  23
H3A   2    0.468485   -0.039031    0.290265    11.00000   -1.20000
H3B   2    0.320214   -0.126090    0.289813    11.00000   -1.20000
AFIX   0
C4    1    0.513888    0.211450    0.518292    11.00000    0.02078    0.01552 =
         0.01872    0.00071    0.00691   -0.00015
AFIX  23
H4A   2    0.494075    0.335459    0.562621    11.00000   -1.20000
H4B   2    0.574118    0.241788    0.455815    11.00000   -1.20000

AFIX   0
HKLF 4

REM  mono in P2(1)/c
REM R1 =  0.0337 for    1032 Fo > 4sig(Fo)  and  0.0363 for all    1114 data
REM     80 parameters refined using      0 restraints

END

WGHT      0.0413      0.2187

REM Instructions for potential hydrogen bonds
HTAB O1 N1
HTAB O1 N2_$1
HTAB N1 O1_$2
HTAB N2 O1_$3

REM Highest difference peak  0.278,  deepest hole -0.185,  1-sigma level  0.042
Q1    1  -0.0220  0.7703  0.4574  11.00000  0.05    0.28
Q2    1   0.0607  0.4900  0.4083  11.00000  0.05    0.24
Q3    1   0.4512 -0.1367  0.4175  11.00000  0.05    0.23
Q4    1   0.0785  0.6302  0.4924  11.00000  0.05    0.20
Q5    1   0.0134  0.6443  0.5787  11.00000  0.05    0.18
Q6    1   0.3307  0.0713  0.4830  11.00000  0.05    0.18
Q7    1   0.1856 -0.0513  0.6228  11.00000  0.05    0.17
Q8    1   0.3979  0.0284  0.3939  11.00000  0.05    0.17
Q9    1   0.4422  0.1661  0.4774  11.00000  0.05    0.16
Q10   1   0.0431  0.5963  0.7382  11.00000  0.05    0.12
;
_shelx_res_checksum              41596
loop_
_space_group_symop_operation_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_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 0.22313(9) 0.08354(12) 0.64085(9) 0.0187(2) Uani 1 1 d . .
H1O H 0.268(2) 0.089(3) 0.576(2) 0.048(5) Uiso 1 1 d . .
H2O H 0.141(2) 0.148(3) 0.600(2) 0.063(6) Uiso 1 1 d . .
N1 N 0.37871(10) 0.12048(14) 0.42187(11) 0.0170(3) Uani 1 1 d . .
H1N H 0.3343(15) 0.206(2) 0.3470(17) 0.021(3) Uiso 1 1 d . .
N2 N 0.04297(10) 0.70430(14) 0.52549(10) 0.0164(3) Uani 1 1 d . .
H2N H 0.0940(18) 0.799(3) 0.5649(19) 0.042(5) Uiso 1 1 d . .
C1 C 0.11639(11) 0.56583(16) 0.45136(12) 0.0142(3) Uani 1 1 d . .
H1A H 0.1978 0.5058 0.5287 0.017 Uiso 1 1 calc R U
H1B H 0.1516 0.6387 0.3794 0.017 Uiso 1 1 calc R U
C2 C -0.01342(11) 0.59708(16) 0.63351(12) 0.0146(3) Uani 1 1 d . .
H2A H -0.0629 0.6902 0.6801 0.017 Uiso 1 1 calc R U
H2B H 0.0651 0.5378 0.7149 0.017 Uiso 1 1 calc R U
C3 C 0.40913(11) -0.06672(17) 0.35418(12) 0.0171(3) Uani 1 1 d . .
H3A H 0.4685 -0.0390 0.2903 0.021 Uiso 1 1 calc R U
H3B H 0.3202 -0.1261 0.2898 0.021 Uiso 1 1 calc R U
C4 C 0.51389(12) 0.21145(16) 0.51829(12) 0.0182(3) Uani 1 1 d . .
H4A H 0.4941 0.3355 0.5626 0.022 Uiso 1 1 calc R U
H4B H 0.5741 0.2418 0.4558 0.022 Uiso 1 1 calc R U
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0173(4) 0.0224(5) 0.0175(4) 0.0001(3) 0.0071(3) -0.0013(3)
N1 0.0152(5) 0.0194(5) 0.0157(5) 0.0051(4) 0.0042(4) 0.0042(4)
N2 0.0196(5) 0.0115(5) 0.0200(5) -0.0017(4) 0.0091(4) -0.0024(4)
C1 0.0139(5) 0.0153(5) 0.0145(5) 0.0013(4) 0.0059(4) -0.0010(4)
C2 0.0158(5) 0.0150(5) 0.0134(5) -0.0016(4) 0.0055(4) -0.0004(4)
C3 0.0163(5) 0.0210(6) 0.0134(5) -0.0001(4) 0.0038(4) -0.0018(4)
C4 0.0208(6) 0.0155(5) 0.0187(6) 0.0007(4) 0.0069(4) -0.0001(4)
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
_geom_angle_site_symmetry_3
C3 N1 C4 109.68(9) .
C2 N2 C1 110.78(9) .
N2 C1 C2 109.91(9) 3_566
N2 C2 C1 109.80(9) 3_566
N1 C3 C4 109.62(9) 3_656
N1 C4 C3 109.32(9) 3_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C3 1.4694(15) .
N1 C4 1.4725(15) .
N2 C2 1.4691(14) .
N2 C1 1.4692(14) .
C1 C2 1.5204(15) 3_566
C2 C1 1.5204(15) 3_566
C3 C4 1.5190(15) 3_656
C4 C3 1.5190(15) 3_656
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
O1 H1O N1 0.86(2) 2.05(2) 2.9033(14) 176.5(18) .
O1 H2O N2 0.89(2) 2.06(2) 2.9393(14) 171.6(19) 3_566
N1 H1N O1 0.890(15) 2.330(16) 3.2187(14) 176.5(13) 4_565
N2 H2N O1 0.819(19) 2.267(19) 3.0793(14) 171.9(16) 1_565
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202382
