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#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/30/8103099.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_8103099
loop_
_publ_author_name
'Wei-Qiu Kan'
'Jian-Fang Ma'
_publ_section_title
;
 Crystal structure of 1,1'-(1,4-butanediyl)bis(imidazolium) 1,4-butylene-
 diphosphonate --- 1,4-butylenediphosphonic acid --- water (1:1:2),
 [C10H16N4][C4H10O6P2] · C4H12O6P2 · 2H2O
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              73
_journal_volume                  226
_journal_year                    2011
_chemical_formula_moiety         'C18 H42 N4 O14 P4'
_chemical_formula_sum            'C18 H42 N4 O14 P4'
_chemical_formula_weight         662.44
_chemical_melting_point          ?
_chemical_name_systematic
;
1,1'-(1,4-butanediyl)bis(imidazole) 1,4-Butylenediphosphonate
;
_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
;
2010-11-18 # Formatted by publCIF
;
_cell_angle_alpha                69.768(5)
_cell_angle_beta                 75.004(5)
_cell_angle_gamma                88.638(5)
_cell_formula_units_Z            1
_cell_length_a                   8.420(5)
_cell_length_b                   9.005(5)
_cell_length_c                   10.608(5)
_cell_measurement_reflns_used    3151
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1575
_cell_measurement_theta_min      3.3222
_cell_volume                     727.1(7)
_computing_cell_refinement       'CrysAlis '
_computing_data_collection       'CrysAlis [4]'
_computing_data_reduction        'CrysAlis '
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5219
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Oxford Diffraction: CrysAlis [4].
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             350
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.158(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2975
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0410
_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)+(0.0712P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1136
_reflns_number_gt                2361
_reflns_number_total             2975
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            1267-3296.cff
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               8103099
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 -0.30465(6) -0.07469(6) 0.85666(6) 0.02369(19) Uani 1 1 d .
P2 P 0.25784(6) 0.54198(6) 0.19547(5) 0.02357(19) Uani 1 1 d .
C1 C 0.7902(3) 0.1381(3) 0.4334(3) 0.0361(6) Uani 1 1 d .
H1 H 0.8654 0.1441 0.4824 0.043 Uiso 1 1 calc R
C2 C 0.6463(3) 0.0524(3) 0.3252(2) 0.0360(5) Uani 1 1 d .
H2 H 0.6060 -0.0123 0.2869 0.043 Uiso 1 1 calc R
C3 C 0.5980(3) 0.1954(3) 0.3228(2) 0.0347(5) Uani 1 1 d .
H3 H 0.5177 0.2490 0.2825 0.042 Uiso 1 1 calc R
C4 C 0.6770(3) 0.4023(3) 0.4109(3) 0.0409(6) Uani 1 1 d .
H4A H 0.6974 0.4866 0.3206 0.049 Uiso 1 1 calc R
H4B H 0.7612 0.4157 0.4543 0.049 Uiso 1 1 calc R
C5 C 0.5102(3) 0.4160(3) 0.5001(3) 0.0344(5) Uani 1 1 d .
H5A H 0.4971 0.3437 0.5949 0.041 Uiso 1 1 calc R
H5B H 0.4250 0.3858 0.4653 0.041 Uiso 1 1 calc R
C6 C -0.0327(2) -0.0051(3) 0.9413(2) 0.0299(5) Uani 1 1 d .
H6A H 0.0316 -0.0764 0.9010 0.036 Uiso 1 1 calc R
H6B H -0.0180 0.0990 0.8690 0.036 Uiso 1 1 calc R
C7 C -0.2135(3) -0.0634(3) 0.9883(2) 0.0305(5) Uani 1 1 d .
H7A H -0.2757 0.0062 1.0319 0.037 Uiso 1 1 calc R
H7B H -0.2261 -0.1682 1.0594 0.037 Uiso 1 1 calc R
C8 C 0.0190(3) 0.5011(3) 0.0663(2) 0.0319(5) Uani 1 1 d .
H8A H -0.0517 0.5724 0.1017 0.038 Uiso 1 1 calc R
H8B H -0.0058 0.3956 0.1365 0.038 Uiso 1 1 calc R
C9 C 0.1985(3) 0.5540(3) 0.0417(2) 0.0302(5) Uani 1 1 d .
H9A H 0.2194 0.6630 -0.0224 0.036 Uiso 1 1 calc R
H9B H 0.2683 0.4893 -0.0031 0.036 Uiso 1 1 calc R
N1 N 0.7661(2) 0.0191(2) 0.3943(2) 0.0349(5) Uani 1 1 d .
H1A H 0.8177 -0.0662 0.4098 0.042 Uiso 1 1 calc R
N2 N 0.6892(2) 0.2485(2) 0.3912(2) 0.0315(4) Uani 1 1 d .
O1 O -0.45805(17) -0.18118(18) 0.91823(16) 0.0340(4) Uani 1 1 d .
O2 O -0.3414(2) 0.09408(17) 0.77285(17) 0.0370(4) Uani 1 1 d .
H2A H -0.2559 0.1518 0.7394 0.055 Uiso 1 1 calc R
O3 O -0.17232(18) -0.13137(18) 0.75392(17) 0.0367(4) Uani 1 1 d .
H3A H -0.0897 -0.0698 0.7220 0.055 Uiso 1 1 calc R
O4 O 0.17450(18) 0.66199(16) 0.25549(17) 0.0347(4) Uani 1 1 d .
O5 O 0.2236(2) 0.37474(16) 0.29795(15) 0.0334(4) Uani 1 1 d .
O6 O 0.44938(17) 0.58021(18) 0.14730(16) 0.0334(4) Uani 1 1 d .
H6 H 0.4713 0.6711 0.0910 0.050 Uiso 1 1 calc R
O1W O 0.0778(2) 0.2510(2) 0.56934(19) 0.0579(6) Uani 1 1 d D
H1WA H 0.1218 0.3250 0.4859 0.087 Uiso 1 1 d RD
H1WB H 0.0113 0.2973 0.6192 0.087 Uiso 1 1 d RD
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
O1 P1 O2 110.31(9) . .
O1 P1 O3 112.20(9) . .
O2 P1 O3 106.76(10) . .
O1 P1 C7 111.51(10) . .
O2 P1 C7 108.64(10) . .
O3 P1 C7 107.22(10) . .
O5 P2 O4 113.00(10) . .
O5 P2 O6 107.57(9) . .
O4 P2 O6 109.93(9) . .
O5 P2 C9 109.58(10) . .
O4 P2 C9 110.73(10) . .
O6 P2 C9 105.72(10) . .
N1 C1 N2 108.5(2) . .
N1 C1 H1 125.7 . .
N2 C1 H1 125.7 . .
C3 C2 N1 107.1(2) . .
C3 C2 H2 126.5 . .
N1 C2 H2 126.5 . .
C2 C3 N2 107.19(19) . .
C2 C3 H3 126.4 . .
N2 C3 H3 126.4 . .
N2 C4 C5 112.0(2) . .
N2 C4 H4A 109.2 . .
C5 C4 H4A 109.2 . .
N2 C4 H4B 109.2 . .
C5 C4 H4B 109.2 . .
H4A C4 H4B 107.9 . .
C4 C5 C5 111.3(2) . 2_666
C4 C5 H5A 109.4 . .
C5 C5 H5A 109.4 2_666 .
C4 C5 H5B 109.4 . .
C5 C5 H5B 109.4 2_666 .
H5A C5 H5B 108.0 . .
C6 C6 C7 113.1(2) 2_557 .
C6 C6 H6A 109.0 2_557 .
C7 C6 H6A 109.0 . .
C6 C6 H6B 109.0 2_557 .
C7 C6 H6B 109.0 . .
H6A C6 H6B 107.8 . .
C6 C7 P1 116.77(16) . .
C6 C7 H7A 108.1 . .
P1 C7 H7A 108.1 . .
C6 C7 H7B 108.1 . .
P1 C7 H7B 108.1 . .
H7A C7 H7B 107.3 . .
C9 C8 C8 112.4(2) . 2_565
C9 C8 H8A 109.1 . .
C8 C8 H8A 109.1 2_565 .
C9 C8 H8B 109.1 . .
C8 C8 H8B 109.1 2_565 .
H8A C8 H8B 107.8 . .
C8 C9 P2 115.16(15) . .
C8 C9 H9A 108.5 . .
P2 C9 H9A 108.5 . .
C8 C9 H9B 108.5 . .
P2 C9 H9B 108.5 . .
H9A C9 H9B 107.5 . .
C1 N1 C2 109.15(18) . .
C1 N1 H1A 125.4 . .
C2 N1 H1A 125.4 . .
C1 N2 C3 108.10(19) . .
C1 N2 C4 126.69(19) . .
C3 N2 C4 125.20(18) . .
P1 O2 H2A 109.5 . .
P1 O3 H3A 109.5 . .
P2 O6 H6 109.5 . .
H1WA O1W H1WB 107.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O1 1.4845(16) .
P1 O2 1.5431(16) .
P1 O3 1.5553(16) .
P1 C7 1.791(2) .
P2 O5 1.5030(16) .
P2 O4 1.5080(15) .
P2 O6 1.5681(17) .
P2 C9 1.794(2) .
C1 N1 1.312(3) .
C1 N2 1.327(3) .
C1 H1 0.9300 .
C2 C3 1.335(3) .
C2 N1 1.364(3) .
C2 H2 0.9300 .
C3 N2 1.375(3) .
C3 H3 0.9300 .
C4 N2 1.468(3) .
C4 C5 1.506(3) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C5 1.517(4) 2_666
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C6 1.516(4) 2_557
C6 C7 1.519(3) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.525(3) .
C8 C8 1.526(4) 2_565
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
N1 H1A 0.8600 .
O2 H2A 0.8200 .
O3 H3A 0.8200 .
O6 H6 0.8200 .
O1W H1WA 0.8937 .
O1W H1WB 0.8691 .
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
N1 H1A O1W 0.86 1.84 2.694(3) 175.1 2_656
O2 H2A O4 0.82 1.85 2.522(2) 138.4 2_566
O3 H3A N1 0.82 2.66 3.387(3) 148.4 2_656
O6 H6 O1 0.82 1.81 2.572(2) 154.4 1_664
O1W H1WA O5 0.89 1.85 2.656(3) 148.7 .
O1W H1WB O4 0.87 1.89 2.732(2) 161.9 2_566
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_1
_geom_torsion_site_symmetry_4
N1 C2 C3 N2 -0.1(3) . .
N2 C4 C5 C5 -170.6(2) . 2_666
C6 C6 C7 P1 178.3(2) 2_557 .
O1 P1 C7 C6 160.59(15) . .
O2 P1 C7 C6 -77.63(19) . .
O3 P1 C7 C6 37.41(19) . .
C8 C8 C9 P2 -174.4(2) 2_565 .
O5 P2 C9 C8 57.13(19) . .
O4 P2 C9 C8 -68.19(19) . .
O6 P2 C9 C8 172.78(15) . .
N2 C1 N1 C2 -0.1(3) . .
C3 C2 N1 C1 0.1(3) . .
N1 C1 N2 C3 0.0(3) . .
N1 C1 N2 C4 -178.9(2) . .
C2 C3 N2 C1 0.0(3) . .
C2 C3 N2 C4 179.0(2) . .
C5 C4 N2 C1 -116.9(3) . .
C5 C4 N2 C3 64.3(3) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139207418
