#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/39/7223928.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_7223928
loop_
_publ_author_name
'Yuan, Liangjie'
'Tian, Di'
'Chen, Shuo-ping'
'Li, Lang'
_publ_section_title
;
 Hydrous salts of 1-aminoethylidenediphosphonic acid and piperazidine:
 temperature induced reversible structural transformation in humid
 environment
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA22428D
_journal_year                    2016
_chemical_formula_sum            'C4 H18 N2 O8 P2'
_chemical_formula_weight         284.14
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-05-14 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                115.505(4)
_cell_angle_beta                 94.461(4)
_cell_angle_gamma                92.251(4)
_cell_formula_units_Z            2
_cell_length_a                   5.7389(14)
_cell_length_b                   9.985(2)
_cell_length_c                   11.457(3)
_cell_measurement_reflns_used    2394
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.44
_cell_measurement_theta_min      2.27
_cell_volume                     588.8(2)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4261
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.400
_exptl_absorpt_correction_T_max  0.9536
_exptl_absorpt_correction_T_min  0.9102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   DADABS
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0328
_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)+(0.0335P)²+0.4003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0841
_reflns_number_gt                2550
_reflns_number_total             2834
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra22428d2.cif
_cod_data_source_block           130922xj_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7223928
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.58818(7) 0.18897(4) 0.17543(4) 0.01772(11) Uani 1 1 d .
P2 P 0.62824(7) 0.49518(4) 0.17367(4) 0.01584(11) Uani 1 1 d .
O4 O 0.3750(2) 0.47249(14) 0.12025(12) 0.0230(3) Uani 1 1 d .
O2 O 0.3505(2) 0.14197(13) 0.09935(13) 0.0255(3) Uani 1 1 d .
O5 O 0.6829(2) 0.57685(13) 0.31770(11) 0.0251(3) Uani 1 1 d .
O3 O 0.5980(2) 0.26801(15) 0.31972(12) 0.0309(3) Uani 1 1 d .
O6 O 0.7803(2) 0.57657(14) 0.11148(12) 0.0237(3) Uani 1 1 d .
H6 H 0.7232 0.5543 0.0370 0.036 Uiso 1 1 calc R
O1 O 0.7445(2) 0.05311(13) 0.13902(13) 0.0256(3) Uani 1 1 d .
H7 H 0.7104 -0.0054 0.0624 0.038 Uiso 1 1 calc R
N3 N 0.9960(2) 0.33803(15) 0.18169(13) 0.0177(3) Uani 1 1 d .
H1A H 1.0631 0.2523 0.1526 0.027 Uiso 1 1 calc R
H1B H 0.9964 0.3752 0.2676 0.027 Uiso 1 1 calc R
H1C H 1.0755 0.4022 0.1616 0.027 Uiso 1 1 calc R
C1 C 0.7477(3) 0.31162(17) 0.11965(14) 0.0150(3) Uani 1 1 d .
C2 C 0.7510(3) 0.23619(19) -0.02843(15) 0.0233(3) Uani 1 1 d .
H2A H 0.8473 0.2975 -0.0542 0.035 Uiso 1 1 calc R
H2B H 0.5942 0.2228 -0.0698 0.035 Uiso 1 1 calc R
H2C H 0.8137 0.1410 -0.0541 0.035 Uiso 1 1 calc R
O7 O 0.6032(3) 0.21929(18) 0.53158(16) 0.0333(3) Uani 1 1 d .
N1 N 0.9503(3) 0.84346(17) 0.44661(17) 0.0336(4) Uani 1 1 d .
H2D H 0.8480 0.7624 0.4175 0.040 Uiso 1 1 calc R
H2E H 1.0959 0.8125 0.4391 0.040 Uiso 1 1 calc R
O8 O 0.2072(3) 0.4224(2) 0.42822(17) 0.0534(5) Uani 1 1 d .
C3 C 0.9071(4) 0.9235(2) 0.3650(2) 0.0358(5) Uani 1 1 d .
H3A H 0.7467 0.9510 0.3675 0.043 Uiso 1 1 calc R
H3B H 0.9297 0.8591 0.2755 0.043 Uiso 1 1 calc R
C4 C 0.9257(4) 0.9383(2) 0.5849(2) 0.0384(5) Uani 1 1 d .
H4A H 0.9590 0.8832 0.6355 0.046 Uiso 1 1 calc R
H4B H 0.7659 0.9664 0.5944 0.046 Uiso 1 1 calc R
H3 H 0.560(5) 0.292(3) 0.583(3) 0.055(9) Uiso 1 1 d .
H4 H 0.607(5) 0.232(3) 0.463(3) 0.051(8) Uiso 1 1 d .
H5 H 0.324(6) 0.385(4) 0.403(3) 0.075(11) Uiso 1 1 d .
H2 H 0.221(6) 0.467(4) 0.506(3) 0.077(11) 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'
P P 0.1023 0.0942 '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_1
_geom_angle_site_symmetry_3
O3 P1 O2 117.60(8) . .
O3 P1 O1 108.38(8) . .
O2 P1 O1 111.22(7) . .
O3 P1 C1 107.72(7) . .
O2 P1 C1 108.02(7) . .
O1 P1 C1 102.82(7) . .
O5 P2 O4 117.20(7) . .
O5 P2 O6 107.34(7) . .
O4 P2 O6 111.29(7) . .
O5 P2 C1 108.07(7) . .
O4 P2 C1 108.56(7) . .
O6 P2 C1 103.47(7) . .
P2 O6 H6 109.5 . .
P1 O1 H7 109.5 . .
C1 N3 H1A 109.5 . .
C1 N3 H1B 109.5 . .
H1A N3 H1B 109.5 . .
C1 N3 H1C 109.5 . .
H1A N3 H1C 109.5 . .
H1B N3 H1C 109.5 . .
N3 C1 C2 108.33(12) . .
N3 C1 P2 107.02(10) . .
C2 C1 P2 111.09(11) . .
N3 C1 P1 107.01(10) . .
C2 C1 P1 110.96(11) . .
P2 C1 P1 112.20(8) . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
H3 O7 H4 106(3) . .
C4 N1 C3 111.99(16) . .
C4 N1 H2D 109.2 . .
C3 N1 H2D 109.2 . .
C4 N1 H2E 109.2 . .
C3 N1 H2E 109.2 . .
H2D N1 H2E 107.9 . .
H5 O8 H2 111(3) . .
N1 C3 C4 109.57(16) . 2_776
N1 C3 H3A 109.8 . .
C4 C3 H3A 109.8 2_776 .
N1 C3 H3B 109.8 . .
C4 C3 H3B 109.8 2_776 .
H3A C3 H3B 108.2 . .
N1 C4 C3 110.06(17) . 2_776
N1 C4 H4A 109.6 . .
C3 C4 H4A 109.6 2_776 .
N1 C4 H4B 109.6 . .
C3 C4 H4B 109.6 2_776 .
H4A C4 H4B 108.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O3 1.4891(14) .
P1 O2 1.5012(13) .
P1 O1 1.5766(13) .
P1 C1 1.8500(16) .
P2 O5 1.4923(13) .
P2 O4 1.5014(12) .
P2 O6 1.5716(12) .
P2 C1 1.8438(16) .
O6 H6 0.8200 .
O1 H7 0.8200 .
N3 C1 1.5024(19) .
N3 H1A 0.8900 .
N3 H1B 0.8900 .
N3 H1C 0.8900 .
C1 C2 1.534(2) .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
O7 H3 0.78(3) .
O7 H4 0.86(3) .
N1 C4 1.476(3) .
N1 C3 1.483(3) .
N1 H2D 0.9000 .
N1 H2E 0.9000 .
O8 H5 0.80(4) .
O8 H2 0.80(3) .
C3 C4 1.511(3) 2_776
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C3 1.511(3) 2_776
C4 H4A 0.9700 .
C4 H4B 0.9700 .
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
O6 H6 O4 0.82 1.75 2.5614(18) 172.3 2_665
O1 H7 O2 0.82 1.76 2.5794(19) 175.3 2_655
N3 H1A O2 0.89 2.01 2.8075(19) 149.1 1_655
N3 H1B O8 0.89 1.98 2.738(2) 141.7 1_655
N3 H1C O4 0.89 2.00 2.8021(18) 149.7 1_655
N1 H2D O5 0.90 1.87 2.750(2) 164.3 .
N1 H2E O7 0.90 1.80 2.680(2) 165.3 2_766
O7 H3 O5 0.78(3) 2.01(3) 2.739(2) 155(3) 2_666
O7 H4 O3 0.86(3) 1.82(3) 2.671(2) 176(3) .
O8 H5 O3 0.80(4) 2.04(4) 2.830(2) 173(3) .
O8 H2 O5 0.80(3) 2.28(3) 2.927(2) 138(3) 2_666
O8 H2 O3 0.80(3) 2.64(3) 3.268(2) 137(3) 2_666
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
_geom_torsion_site_symmetry_4
O5 P2 C1 N3 -48.41(11) .
O4 P2 C1 N3 -176.50(9) .
O6 P2 C1 N3 65.19(11) .
O5 P2 C1 C2 -166.49(11) .
O4 P2 C1 C2 65.43(12) .
O6 P2 C1 C2 -52.88(12) .
O5 P2 C1 P1 68.67(9) .
O4 P2 C1 P1 -59.41(9) .
O6 P2 C1 P1 -177.72(7) .
O3 P1 C1 N3 60.53(12) .
O2 P1 C1 N3 -171.49(9) .
O1 P1 C1 N3 -53.82(11) .
O3 P1 C1 C2 178.52(11) .
O2 P1 C1 C2 -53.50(13) .
O1 P1 C1 C2 64.17(12) .
O3 P1 C1 P2 -56.56(10) .
O2 P1 C1 P2 71.42(9) .
O1 P1 C1 P2 -170.91(8) .
C4 N1 C3 C4 57.6(2) 2_776
C3 N1 C4 C3 -57.9(2) 2_776
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139201499
