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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/7/22/58/7225859.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_7225859
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 H9 N2 O2, C4 H11 N2'
_chemical_formula_sum            'C9 H20 N4 O2'
_chemical_formula_weight         216.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.194(3)
_cell_length_b                   9.572(5)
_cell_length_c                   18.884(10)
_cell_measurement_reflns_used    1649
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.26
_cell_measurement_theta_min      4.26
_cell_volume                     1119.6(10)
_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 0.993
_diffrn_measured_fraction_theta_max 0.994
_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  0.0612
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9568
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         4.258
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.526
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 632 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0507P)²+0.0647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1016
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1782
_reflns_number_total             2193
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01083k1.cif
_cod_data_source_block           PZH-PZCOO
_cod_depositor_comments
'Adding full bibliography for 7225856--7225859.cif.'
_cod_original_cell_volume        1119.7(10)
_cod_database_code               7225859
_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   0.953
_shelx_estimated_absorpt_t_max   0.994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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 0.7013(3) 0.2379(2) 0.59611(10) 0.0269(5) Uani 1 1 d . .
O2 O 0.3504(3) 0.2498(2) 0.62540(10) 0.0232(5) Uani 1 1 d . .
N1 N 0.6010(4) 0.2012(3) 0.70890(12) 0.0225(6) Uani 1 1 d . .
N2 N 0.6926(4) 0.0540(3) 0.83421(13) 0.0219(6) Uani 1 1 d . .
H1N H 0.703(5) -0.030(4) 0.8571(17) 0.028(9) Uiso 1 1 d . .
C1 C 0.5486(5) 0.2315(3) 0.64020(14) 0.0191(6) Uani 1 1 d . .
C2 C 0.8231(4) 0.1876(3) 0.73289(16) 0.0236(7) Uani 1 1 d . .
H2A H 0.8615 0.2670 0.7622 0.028 Uiso 1 1 calc R U
H2B H 0.9195 0.1856 0.6924 0.028 Uiso 1 1 calc R U
C3 C 0.8461(5) 0.0545(3) 0.77491(16) 0.0253(7) Uani 1 1 d . .
H3A H 0.8188 -0.0253 0.7445 0.030 Uiso 1 1 calc R U
H3B H 0.9923 0.0469 0.7929 0.030 Uiso 1 1 calc R U
C4 C 0.4710(5) 0.0629(3) 0.80723(16) 0.0228(7) Uani 1 1 d . .
H4A H 0.3701 0.0617 0.8465 0.027 Uiso 1 1 calc R U
H4B H 0.4409 -0.0171 0.7773 0.027 Uiso 1 1 calc R U
C5 C 0.4428(5) 0.1959(3) 0.76524(15) 0.0231(7) Uani 1 1 d . .
H5A H 0.2985 0.1992 0.7453 0.028 Uiso 1 1 calc R U
H5B H 0.4606 0.2760 0.7961 0.028 Uiso 1 1 calc R U
N3 N 0.7685(4) 0.6880(3) 0.43920(13) 0.0233(6) Uani 1 1 d . .
H2N H 0.792(5) 0.760(3) 0.4064(18) 0.029(9) Uiso 1 1 d . .
N4 N 0.7335(4) 0.4081(3) 0.48700(13) 0.0191(6) Uani 1 1 d . .
H3N H 0.777(5) 0.349(4) 0.4447(19) 0.040(10) Uiso 1 1 d . .
H4N H 0.709(5) 0.337(4) 0.5260(18) 0.030(9) Uiso 1 1 d . .
C6 C 0.9633(5) 0.6041(3) 0.44882(16) 0.0227(7) Uani 1 1 d . .
H6A H 1.0829 0.6638 0.4623 0.027 Uiso 1 1 calc R U
H6B H 1.0004 0.5579 0.4048 0.027 Uiso 1 1 calc R U
C7 C 0.9230(5) 0.4970(3) 0.50566(15) 0.0229(7) Uani 1 1 d . .
H7A H 1.0499 0.4387 0.5112 0.028 Uiso 1 1 calc R U
H7B H 0.8962 0.5438 0.5504 0.028 Uiso 1 1 calc R U
C8 C 0.5384(5) 0.4934(3) 0.47084(16) 0.0220(6) Uani 1 1 d . .
H8A H 0.4887 0.5397 0.5135 0.026 Uiso 1 1 calc R U
H8B H 0.4234 0.4332 0.4540 0.026 Uiso 1 1 calc R U
C9 C 0.5913(5) 0.6010(3) 0.41522(16) 0.0237(7) Uani 1 1 d . .
H9A H 0.6310 0.5547 0.3714 0.028 Uiso 1 1 calc R U
H9B H 0.4655 0.6586 0.4061 0.028 Uiso 1 1 calc R U
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 C5 122.9(2)
C1 N1 C2 122.6(2)
C5 N1 C2 114.1(2)
C4 N2 C3 109.9(2)
O1 C1 O2 124.9(3)
O1 C1 N1 117.3(3)
O2 C1 N1 117.8(2)
N1 C2 C3 109.3(3)
N2 C3 C2 110.0(3)
N2 C4 C5 109.9(3)
N1 C5 C4 109.7(2)
C9 N3 C6 110.4(2)
C8 N4 C7 112.0(2)
N3 C6 C7 109.0(2)
N4 C7 C6 110.5(2)
N4 C8 C9 109.9(2)
N3 C9 C8 109.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.262(3)
O2 C1 1.271(3)
N1 C1 1.368(3)
N1 C5 1.447(4)
N1 C2 1.454(4)
N2 C4 1.466(4)
N2 C3 1.469(4)
C2 C3 1.508(4)
C4 C5 1.510(4)
N3 C9 1.450(4)
N3 C6 1.461(4)
N4 C8 1.490(4)
N4 C7 1.492(4)
C6 C7 1.505(4)
C8 C9 1.507(4)
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 O2 0.92(3) 2.16(3) 3.022(4) 157(3) 3_646
N3 H2N N2 0.94(3) 2.24(3) 3.176(4) 172(3) 2_664
N4 H3N O2 1.02(4) 1.69(4) 2.704(3) 180(3) 4_556
N4 H4N O1 1.01(3) 1.63(4) 2.635(3) 170(3) .
C6 H6A N3 0.97 2.61 3.465(4) 147.7 4_566
C8 H8B O1 0.97 2.34 3.295(4) 168.8 4_456
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139202384
