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#$Date: 2025-01-06 13:49:19 +0200 (Mon, 06 Jan 2025) $
#$Revision: 297107 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249608.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_7249608
loop_
_publ_author_name
'Budzikur-Maciąg, Daria'
'Kinzhybalo, Vasyl'
'Ślepokura, Katarzyna'
_publ_section_title
;
 Structural landscape studies of aminopyridinium hypodiphosphates:
 dehydration and polymorphism in 4-aminopyridinium salts
;
_journal_issue                   48
_journal_name_full               CrystEngComm
_journal_page_first              6861
_journal_page_last               6872
_journal_paper_doi               10.1039/D4CE01048E
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         '2(C5 H7 N2), (H2 P2 O6), 2(H2 O)'
_chemical_formula_sum            'C10 H20 N4 O8 P2'
_chemical_formula_weight         386.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2024-08-15 deposited with the CCDC.	2024-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                104.55(3)
_cell_angle_beta                 93.32(3)
_cell_angle_gamma                117.03(4)
_cell_formula_units_Z            1
_cell_length_a                   6.999(3)
_cell_length_b                   7.137(3)
_cell_length_c                   9.596(3)
_cell_measurement_reflns_used    6989
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      47.8470
_cell_measurement_theta_min      2.2370
_cell_volume                     405.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.80a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.573
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0138
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.573
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10188
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.573
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         48.218
_diffrn_reflns_theta_min         2.238
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.80a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_description       plate
_exptl_crystal_F_000             202
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.065
_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     130
_refine_ls_number_reflns         4490
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0269
_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)+(0.0419P)²+0.0651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0782
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3875
_reflns_number_total             4490
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01048e2.cif
_cod_data_source_block           4ampyr21_aa
_cod_depositor_comments
'Adding full bibliography for 7249606--7249610.cif.'
_cod_database_code               7249608
_shelx_shelxl_version_number     2016/6
_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   0.939
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.87477(2) 0.92530(2) 1.06163(2) 0.00684(4) Uani 1 1 d . . . . .
O1 O 0.85633(8) 1.10820(8) 1.16816(6) 0.01119(8) Uani 1 1 d . . . . .
O2 O 0.66836(7) 0.74369(8) 0.95540(5) 0.01028(8) Uani 1 1 d . . . . .
O3 O 0.97605(8) 0.81950(8) 1.15063(6) 0.01092(8) Uani 1 1 d . . . . .
H3P H 0.923(3) 0.685(3) 1.1194(17) 0.036(4) Uiso 1 1 d . . . . .
N1 N 0.59511(11) 0.44126(10) 0.69729(7) 0.01466(10) Uani 1 1 d . . . . .
H1N H 0.625(3) 0.536(3) 0.7853(17) 0.040(4) Uiso 1 1 d . . . . .
C2 C 0.75851(11) 0.42519(11) 0.63686(8) 0.01461(12) Uani 1 1 d . . . . .
H2 H 0.903448 0.507057 0.693315 0.018 Uiso 1 1 calc R U . . .
C3 C 0.72006(10) 0.29378(11) 0.49630(8) 0.01191(10) Uani 1 1 d . . . . .
H3 H 0.837418 0.284834 0.455727 0.014 Uiso 1 1 calc R U . . .
C4 C 0.50375(10) 0.17040(10) 0.41087(7) 0.00927(9) Uani 1 1 d . . . . .
N4 N 0.46220(9) 0.04074(10) 0.27388(6) 0.01157(9) Uani 1 1 d . . . . .
H4N1 H 0.333(2) -0.027(2) 0.2265(14) 0.022(3) Uiso 1 1 d . . . . .
H4N2 H 0.571(2) 0.044(2) 0.2380(13) 0.016(3) Uiso 1 1 d . . . . .
C5 C 0.33570(10) 0.19024(11) 0.47874(8) 0.01192(10) Uani 1 1 d . . . . .
H5 H 0.188423 0.109761 0.426250 0.014 Uiso 1 1 calc R U . . .
C6 C 0.38714(12) 0.32572(11) 0.61990(8) 0.01416(11) Uani 1 1 d . . . . .
H6 H 0.274315 0.338930 0.664547 0.017 Uiso 1 1 calc R U . . .
O1W O 0.76409(8) 0.39023(9) 1.05366(8) 0.01904(11) Uani 1 1 d DG . . . .
H1W1 H 0.628832 0.344494 1.046166 0.041(4) Uiso 1 1 d DG . . . .
H1W2 H 0.793362 0.305372 1.086365 0.029(3) Uiso 1 1 d DG . . . .
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
_geom_angle_publ_flag
O1 P1 O2 116.79(5) . . yes
O1 P1 O3 109.24(4) . . yes
O2 P1 O3 109.35(5) . . yes
O1 P1 P1 108.05(5) . 2_777 yes
O2 P1 P1 109.20(4) . 2_777 yes
O3 P1 P1 103.36(4) . 2_777 yes
P1 O3 H3P 115.7(11) . . ?
C2 N1 C6 120.60(7) . . ?
C2 N1 H1N 120.2(11) . . ?
C6 N1 H1N 119.0(11) . . ?
N1 C2 C3 121.42(7) . . ?
N1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 119.76(7) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
N4 C4 C5 121.98(7) . . ?
N4 C4 C3 120.84(7) . . ?
C5 C4 C3 117.18(7) . . ?
C4 N4 H4N1 117.7(9) . . ?
C4 N4 H4N2 117.2(8) . . ?
H4N1 N4 H4N2 124.7(12) . . ?
C6 C5 C4 119.66(7) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
N1 C6 C5 121.39(8) . . ?
N1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
H1W1 O1W H1W2 107.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.5045(8) . yes
P1 O2 1.5066(12) . yes
P1 O3 1.5945(7) . yes
P1 P1 2.1873(10) 2_777 yes
O3 H3P 0.818(16) . ?
N1 C2 1.3491(11) . ?
N1 C6 1.3514(13) . ?
N1 H1N 0.885(16) . ?
C2 C3 1.3654(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.4217(13) . ?
C3 H3 0.9500 . ?
C4 N4 1.3300(11) . ?
C4 C5 1.4217(11) . ?
N4 H4N1 0.841(13) . ?
N4 H4N2 0.846(12) . ?
C5 C6 1.3669(12) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
O1W H1W1 0.8410 . ?
O1W H1W2 0.8415 . ?
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
O3 H3P O1W 0.818(16) 1.784(16) 2.594 170.6(16) .
N1 H1N O2 0.885(16) 1.806(16) 2.6865(15) 173.5(16) .
N4 H4N1 O3 0.841(13) 2.205(14) 3.030(2) 167.2(12) 1_444
N4 H4N2 O1 0.846(12) 2.032(12) 2.8693(15) 170.1(11) 1_544
C2 H2 O1 0.95 2.42 3.160(2) 134.8 2_777
C6 H6 O3 0.95 2.66 3.4329(16) 139.2 2_667
O1W H1W1 O2 0.84 1.88 2.717 175.5 2_667
O1W H1W2 O1 0.84 1.97 2.808 178.1 1_545
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 0.40(11) . . . . ?
N1 C2 C3 C4 -0.05(10) . . . . ?
C2 C3 C4 N4 -179.78(6) . . . . ?
C2 C3 C4 C5 -0.45(9) . . . . ?
N4 C4 C5 C6 179.95(6) . . . . ?
C3 C4 C5 C6 0.62(9) . . . . ?
C2 N1 C6 C5 -0.21(10) . . . . ?
C4 C5 C6 N1 -0.31(10) . . . . ?
O1 P1 P1 O1 180 . . 2_777 2_777 yes
O2 P1 P1 O1 -52.02(5) . . 2_777 2_777 yes
O3 P1 P1 O1 64.30(5) . . 2_777 2_777 yes
O1 P1 P1 O2 52.02(5) . . 2_777 2_777 yes
O2 P1 P1 O2 180 . . 2_777 2_777 yes
O3 P1 P1 O2 -63.68(4) . . 2_777 2_777 yes
O1 P1 P1 O3 -64.30(5) . . 2_777 2_777 yes
O2 P1 P1 O3 63.68(4) . . 2_777 2_777 yes
O3 P1 P1 O3 180 . . 2_777 2_777 yes
