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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/7/24/96/7249606.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_7249606
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), (H4 P2 O6), 2(H2 O)'
_chemical_formula_sum            'C10 H24 N4 O14 P4'
_chemical_formula_weight         548.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                90
_cell_angle_beta                 108.97(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2355(13)
_cell_length_b                   18.528(3)
_cell_length_c                   8.8381(14)
_cell_measurement_reflns_used    12838
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.3870
_cell_measurement_theta_min      3.8500
_cell_volume                     1120.5(4)
_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                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Agilent Technologies Xcalibur R, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            30195
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.651
_diffrn_reflns_theta_min         3.174
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.80a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         5756
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0262
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0344P)²+0.1974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0720
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4944
_reflns_number_total             5756
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01048e2.cif
_cod_data_source_block           4amino11m-smart
_cod_depositor_comments
'Adding full bibliography for 7249606--7249610.cif.'
_cod_original_cell_volume        1120.5(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7249606
_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   0.905
_shelx_estimated_absorpt_t_max   0.945
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1A P 0.61120(3) 0.54090(2) 0.50907(2) 0.01076(4) Uani 1 1 d . . . . .
O1A O 0.68424(8) 0.56895(3) 0.67627(6) 0.01466(10) Uani 1 1 d . . . . .
O2A O 0.51345(9) 0.60164(3) 0.39100(7) 0.01690(10) Uani 1 1 d . . . . .
H2PA H 0.466(3) 0.5892(12) 0.272(2) 0.070(6) Uiso 1 1 d . . . . .
O3A O 0.77694(8) 0.50379(4) 0.46306(7) 0.01694(10) Uani 1 1 d . . . . .
H3PA H 0.758(3) 0.4908(11) 0.379(2) 0.061(5) Uiso 1 1 d . . . . .
P1B P 0.35867(3) 0.52460(2) -0.01574(2) 0.01129(4) Uani 1 1 d . . . . .
O1B O 0.26708(9) 0.54549(3) -0.18860(6) 0.01545(10) Uani 1 1 d . . . . .
O2B O 0.38801(9) 0.58749(3) 0.09853(6) 0.01567(10) Uani 1 1 d . . . . .
O3B O 0.23292(9) 0.46360(3) 0.02606(7) 0.01732(10) Uani 1 1 d . . . . .
H3PB H 0.259(3) 0.4572(9) 0.118(2) 0.051(5) Uiso 1 1 d . . . . .
N1 N 1.01779(10) 0.68705(4) 1.12073(8) 0.01774(12) Uani 1 1 d . . . . .
H1N H 1.028(2) 0.6724(8) 1.0303(17) 0.033(4) Uiso 1 1 d . . . . .
C2 C 1.02730(12) 0.64012(4) 1.23989(9) 0.01749(13) Uani 1 1 d . . . . .
H2 H 1.041805 0.590021 1.223793 0.021 Uiso 1 1 calc R U . . .
C3 C 1.01639(12) 0.66358(4) 1.38314(9) 0.01600(12) Uani 1 1 d . . . . .
H3 H 1.024240 0.629981 1.466191 0.019 Uiso 1 1 calc R U . . .
C4 C 0.99333(11) 0.73821(4) 1.40773(9) 0.01403(12) Uani 1 1 d . . . . .
N4 N 0.98025(12) 0.76296(4) 1.54576(8) 0.01894(13) Uani 1 1 d . . . . .
H4N1 H 0.9594(19) 0.8075(8) 1.5579(16) 0.027(3) Uiso 1 1 d . . . . .
H4N2 H 0.9851(19) 0.7341(8) 1.6210(17) 0.029(3) Uiso 1 1 d . . . . .
C5 C 0.98577(12) 0.78576(4) 1.28001(9) 0.01628(12) Uani 1 1 d . . . . .
H5 H 0.971913 0.836242 1.291800 0.020 Uiso 1 1 calc R U . . .
C6 C 0.99851(12) 0.75864(4) 1.14008(9) 0.01755(13) Uani 1 1 d . . . . .
H6 H 0.993730 0.790660 1.054935 0.021 Uiso 1 1 calc R U . . .
O1W O 1.00434(8) 0.65724(3) 0.80117(7) 0.01489(10) Uani 1 1 d DG . . . .
H1W1 H 0.896540 0.636215 0.760124 0.040(4) Uiso 1 1 d DG . . . .
H1W2 H 1.093412 0.627646 0.803486 0.040(4) 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
O1A P1A O2A 110.67(4) . . yes
O1A P1A O3A 111.10(4) . . yes
O2A P1A O3A 111.77(4) . . yes
O1A P1A P1A 109.32(3) . 3_666 yes
O2A P1A P1A 107.02(3) . 3_666 yes
O3A P1A P1A 106.78(3) . 3_666 yes
P1A O2A H2PA 117.3(12) . . ?
P1A O3A H3PA 119.5(14) . . ?
O1B P1B O2B 113.58(3) . . yes
O1B P1B O3B 109.07(4) . . yes
O2B P1B O3B 111.37(4) . . yes
O1B P1B P1B 108.87(3) . 3_665 yes
O2B P1B P1B 108.42(3) . 3_665 yes
O3B P1B P1B 105.16(3) . 3_665 yes
P1B O2B H2PA 130.1(9) . . ?
P1B O3B H3PB 112.9(12) . . ?
C2 N1 C6 121.00(7) . . ?
C2 N1 H1N 121.2(10) . . ?
C6 N1 H1N 117.8(10) . . ?
N1 C2 C3 120.98(7) . . ?
N1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 119.86(7) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
N4 C4 C3 121.46(7) . . ?
N4 C4 C5 121.18(7) . . ?
C3 C4 C5 117.36(7) . . ?
C4 N4 H4N1 121.0(9) . . ?
C4 N4 H4N2 120.3(10) . . ?
H4N1 N4 H4N2 118.6(13) . . ?
C6 C5 C4 119.70(7) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
N1 C6 C5 121.08(7) . . ?
N1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
H1W1 O1W H1W2 107.7 . . ?
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
P1A O1A 1.4918(6) . yes
P1A O2A 1.5414(6) . yes
P1A O3A 1.5471(6) . yes
P1A P1A 2.1781(5) 3_666 yes
O2A H2PA 1.021(19) . ?
O3A H3PA 0.751(19) . ?
P1B O1B 1.5049(6) . yes
P1B O2B 1.5112(6) . yes
P1B O3B 1.5685(6) . yes
P1B P1B 2.1727(5) 3_665 yes
O2B H2PA 1.452(19) . ?
O3B H3PB 0.783(17) . ?
N1 C2 1.3500(11) . ?
N1 C6 1.3505(11) . ?
N1 H1N 0.870(14) . ?
C2 C3 1.3649(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.4179(11) . ?
C3 H3 0.9500 . ?
C4 N4 1.3352(10) . ?
C4 C5 1.4189(10) . ?
N4 H4N1 0.852(14) . ?
N4 H4N2 0.846(14) . ?
C5 C6 1.3655(11) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
O1W H1W1 0.8413 . ?
O1W H1W2 0.8413 . ?
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
O2A H2PA O2B 1.021(19) 1.452(19) 2.4594(9) 168(2) .
O3A H3PA O1B 0.751(19) 1.765(19) 2.5133(9) 174(2) 3_665
O3B H3PB O1A 0.783(17) 1.794(17) 2.5728(9) 173.1(18) 3_666
N1 H1N O1W 0.870(14) 1.996(14) 2.848 166.2(14) .
N4 H4N1 O2B 0.852(14) 2.074(14) 2.9228(10) 174.1(12) 4_677
N4 H4N2 O1W 0.846(14) 2.106(14) 2.951 176.5(13) 1_556
C2 H2 O3B 0.95 2.64 3.1441(11) 113.8 3_666
C6 H6 O2A 0.95 2.50 3.4226(11) 164.7 4_676
O1W H1W1 O1A 0.84 1.93 2.756 167.3 .
O1W H1W2 O1B 0.84 1.96 2.792 169.7 1_656
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 0.44(12) . . . . ?
N1 C2 C3 C4 0.46(12) . . . . ?
C2 C3 C4 N4 179.35(8) . . . . ?
C2 C3 C4 C5 -1.01(11) . . . . ?
N4 C4 C5 C6 -179.65(8) . . . . ?
C3 C4 C5 C6 0.70(11) . . . . ?
C2 N1 C6 C5 -0.76(13) . . . . ?
C4 C5 C6 N1 0.16(12) . . . . ?
O1A P1A P1A O1A 180 . . 3_666 3_666 yes
O2A P1A P1A O1A 60.10(4) . . 3_666 3_666 yes
O3A P1A P1A O1A -59.73(4) . . 3_666 3_666 yes
O1A P1A P1A O2A -60.10(4) . . 3_666 3_666 yes
O2A P1A P1A O2A 180 . . 3_666 3_666 yes
O3A P1A P1A O2A 60.17(4) . . 3_666 3_666 yes
O1A P1A P1A O3A 59.73(4) . . 3_666 3_666 yes
O2A P1A P1A O3A -60.17(4) . . 3_666 3_666 yes
O3A P1A P1A O3A 180 . . 3_666 3_666 yes
O1B P1B P1B O1B 180 . . 3_665 3_665 yes
O2B P1B P1B O1B 55.99(4) . . 3_665 3_665 yes
O3B P1B P1B O1B -63.24(4) . . 3_665 3_665 yes
O1B P1B P1B O2B -55.99(4) . . 3_665 3_665 yes
O2B P1B P1B O2B 180 . . 3_665 3_665 yes
O3B P1B P1B O2B 60.78(4) . . 3_665 3_665 yes
O1B P1B P1B O3B 63.24(4) . . 3_665 3_665 yes
O2B P1B P1B O3B -60.78(4) . . 3_665 3_665 yes
O3B P1B P1B O3B 180 . . 3_665 3_665 yes
