#------------------------------------------------------------------------------
#$Date: 2025-01-06 13:49:19 +0200 (Mon, 06 Jan 2025) $
#$Revision: 297107 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249610.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_7249610
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)'
_chemical_formula_sum            'C10 H16 N4 O6 P2'
_chemical_formula_weight         350.21
_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'
_atom_sites_solution_hydrogens   geom
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.496(2)
_cell_length_b                   16.008(3)
_cell_length_c                   15.982(2)
_cell_measurement_reflns_used    14962
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.8740
_cell_measurement_theta_min      3.8850
_cell_volume                     3197.0(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            47060
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         73.750
_diffrn_reflns_theta_min         2.760
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 2220 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         6332
_refine_ls_number_restraints     570
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0555P)²+0.4441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                5673
_reflns_number_total             6332
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01048e2.cif
_cod_data_source_block           4ap21-deh-110C
_cod_depositor_comments
'Adding full bibliography for 7249606--7249610.cif.'
_cod_database_code               7249610
_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   0.921
_shelx_estimated_absorpt_t_max   0.946
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1A P 0.48216(16) 0.50587(12) 0.51030(12) 0.0229(4) Uani 1 1 d . U . . .
O1A O 0.5805(5) 0.4534(3) 0.5143(4) 0.0299(13) Uani 1 1 d . U . . .
O2A O 0.3812(5) 0.4738(4) 0.5491(3) 0.0310(13) Uani 1 1 d . U . . .
O3A O 0.4643(4) 0.5288(4) 0.4150(3) 0.0293(13) Uani 1 1 d . U . . .
H3PA H 0.410652 0.560099 0.410484 0.044 Uiso 1 1 calc R U . . .
P2A P 0.51559(17) 0.62538(13) 0.57074(11) 0.0218(4) Uani 1 1 d . U . . .
O4A O 0.5277(4) 0.6135(4) 0.6634(3) 0.0284(13) Uani 1 1 d . U . . .
O5A O 0.6119(4) 0.6633(3) 0.5276(3) 0.0269(12) Uani 1 1 d . U . . .
O6A O 0.4127(4) 0.6784(4) 0.5558(3) 0.0278(12) Uani 1 1 d . U . . .
H6PA H 0.413105 0.697260 0.506773 0.042 Uiso 1 1 calc R U . . .
P1B P 0.23171(16) 0.73770(13) 0.24966(12) 0.0229(4) Uani 1 1 d . U . . .
O1B O 0.1374(5) 0.6935(4) 0.2119(4) 0.0327(14) Uani 1 1 d . U . . .
O2B O 0.3337(5) 0.7423(4) 0.1993(3) 0.0307(13) Uani 1 1 d . U . . .
O3B O 0.2042(4) 0.8306(4) 0.2737(4) 0.0294(12) Uani 1 1 d . U . . .
H3PB H 0.139846 0.833686 0.288615 0.044 Uiso 1 1 calc R U . . .
P2B P 0.26763(17) 0.67702(13) 0.36860(12) 0.0224(4) Uani 1 1 d . U . . .
O4B O 0.2825(4) 0.5844(3) 0.3574(3) 0.0268(12) Uani 1 1 d . U . . .
O5B O 0.3635(4) 0.7223(3) 0.4063(3) 0.0264(12) Uani 1 1 d . U . . .
O6B O 0.1650(4) 0.6903(4) 0.4243(3) 0.0273(12) Uani 1 1 d . U . . .
H6PB H 0.151287 0.741521 0.427703 0.041 Uiso 1 1 calc R U . . .
N1A N 0.7530(7) 0.5952(5) 0.4173(5) 0.051(2) Uani 1 1 d . U . . .
H1NA H 0.699469 0.605567 0.451582 0.061 Uiso 1 1 calc R U . . .
C2A C 0.8199(8) 0.6577(7) 0.3936(7) 0.052(3) Uani 1 1 d . U . . .
H2A H 0.808225 0.712551 0.414324 0.062 Uiso 1 1 calc R U . . .
C3A C 0.9031(7) 0.6434(6) 0.3408(6) 0.043(2) Uani 1 1 d . U . . .
H3A H 0.949308 0.688006 0.325498 0.051 Uiso 1 1 calc R U . . .
C4A C 0.9210(7) 0.5623(5) 0.3086(5) 0.0322(19) Uani 1 1 d . U . . .
N4A N 1.0027(6) 0.5491(4) 0.2556(4) 0.0303(15) Uani 1 1 d . U . . .
H4A1 H 1.014194 0.498729 0.235359 0.036 Uiso 1 1 calc R U . . .
H4A2 H 1.044674 0.590751 0.240996 0.036 Uiso 1 1 calc R U . . .
C5A C 0.8515(8) 0.4998(6) 0.3345(6) 0.042(2) Uani 1 1 d . U . . .
H5A H 0.861234 0.444348 0.314646 0.051 Uiso 1 1 calc R U . . .
C6A C 0.7689(8) 0.5170(7) 0.3882(6) 0.047(2) Uani 1 1 d . U . . .
H6A H 0.722227 0.473281 0.405205 0.057 Uiso 1 1 calc R U . . .
N1B N 0.5121(7) 0.8239(5) 0.3336(5) 0.050(2) Uani 1 1 d . U . . .
H1NB H 0.457277 0.790213 0.340857 0.060 Uiso 1 1 calc R U . . .
C2B C 0.5751(8) 0.8431(7) 0.3985(6) 0.049(3) Uani 1 1 d . U . . .
H2B H 0.560409 0.818720 0.451476 0.059 Uiso 1 1 calc R U . . .
C3B C 0.6594(7) 0.8962(6) 0.3911(5) 0.039(2) Uani 1 1 d . U . . .
H3B H 0.704450 0.907355 0.437688 0.047 Uiso 1 1 calc R U . . .
C4B C 0.6790(7) 0.9347(6) 0.3130(5) 0.0329(19) Uani 1 1 d . U . . .
N4B N 0.7542(6) 0.9918(5) 0.3023(4) 0.0359(17) Uani 1 1 d . U . . .
H4B1 H 0.794367 1.007151 0.344809 0.043 Uiso 1 1 calc R U . . .
H4B2 H 0.764041 1.014348 0.252715 0.043 Uiso 1 1 calc R U . . .
C5B C 0.6122(8) 0.9098(6) 0.2458(6) 0.039(2) Uani 1 1 d . U . . .
H5B H 0.624618 0.931887 0.191465 0.046 Uiso 1 1 calc R U . . .
C6B C 0.5319(9) 0.8556(7) 0.2576(6) 0.048(2) Uani 1 1 d . U . . .
H6B H 0.488525 0.839453 0.211567 0.058 Uiso 1 1 calc R U . . .
N1C N 0.5042(6) 0.6543(5) 0.1669(5) 0.033(2) Uani 0.702(11) 1 d D U P A 1
H1NC H 0.448837 0.687664 0.173260 0.039 Uiso 0.702(11) 1 calc R U P A 1
C2C C 0.5796(9) 0.6709(7) 0.1069(8) 0.036(3) Uani 0.702(11) 1 d D U P A 1
H2C H 0.572636 0.719745 0.073662 0.044 Uiso 0.702(11) 1 calc R U P A 1
C3C C 0.6643(10) 0.6191(8) 0.0939(8) 0.039(3) Uani 0.702(11) 1 d D U P A 1
H3C H 0.716096 0.632055 0.052379 0.047 Uiso 0.702(11) 1 calc R U P A 1
C4C C 0.6744(8) 0.5463(7) 0.1421(7) 0.037(2) Uani 0.702(11) 1 d D U P A 1
N4C N 0.7567(7) 0.4943(6) 0.1304(6) 0.038(3) Uani 0.702(11) 1 d D U P A 1
H4C1 H 0.764667 0.450523 0.163074 0.046 Uiso 0.702(11) 1 calc R U P A 1
H4C2 H 0.802889 0.503814 0.089909 0.046 Uiso 0.702(11) 1 calc R U P A 1
C5C C 0.5996(8) 0.5328(7) 0.2059(7) 0.035(3) Uani 0.702(11) 1 d D U P A 1
H5C H 0.607313 0.486140 0.242157 0.042 Uiso 0.702(11) 1 calc R U P A 1
C6C C 0.5155(9) 0.5865(7) 0.2162(7) 0.035(2) Uani 0.702(11) 1 d D U P A 1
H6C H 0.464258 0.575839 0.258828 0.042 Uiso 0.702(11) 1 calc R U P A 1
N1D N 0.2162(7) 0.4004(6) 0.4689(5) 0.031(2) Uani 0.761(12) 1 d D U P B 1
H1ND H 0.259395 0.441723 0.482181 0.037 Uiso 0.761(12) 1 calc R U P B 1
C2D C 0.1514(9) 0.4080(8) 0.4037(6) 0.032(2) Uani 0.761(12) 1 d D U P B 1
H2D H 0.151536 0.458512 0.372450 0.039 Uiso 0.761(12) 1 calc R U P B 1
C3D C 0.0851(10) 0.3455(7) 0.3810(8) 0.031(2) Uani 0.761(12) 1 d . U P B 1
H3D H 0.039615 0.352248 0.333890 0.037 Uiso 0.761(12) 1 calc R U P B 1
C4D C 0.0830(9) 0.2688(7) 0.4278(7) 0.0243(19) Uani 0.761(12) 1 d . U P B 1
N4D N 0.0201(8) 0.2059(7) 0.4080(7) 0.031(3) Uani 0.761(12) 1 d . U P B 1
H4D1 H 0.020847 0.160069 0.438417 0.038 Uiso 0.761(12) 1 calc R U P B 1
H4D2 H -0.022664 0.209693 0.364475 0.038 Uiso 0.761(12) 1 calc R U P B 1
C5D C 0.1538(9) 0.2664(7) 0.4973(6) 0.0256(19) Uani 0.761(12) 1 d . U P B 1
H5D H 0.155727 0.218027 0.531731 0.031 Uiso 0.761(12) 1 calc R U P B 1
C6D C 0.2168(12) 0.3301(11) 0.5149(10) 0.034(3) Uani 0.761(12) 1 d . U P B 1
H6D H 0.263871 0.326204 0.561425 0.041 Uiso 0.761(12) 1 calc R U P B 1
N1X N 0.7387(16) 0.5731(15) 0.0892(13) 0.052(6) Uiso 0.298(11) 1 d D U P A 2
H1NX H 0.792837 0.564256 0.055045 0.062 Uiso 0.298(11) 1 calc R U P A 2
C2X C 0.663(2) 0.632(2) 0.0704(16) 0.048(7) Uiso 0.298(11) 1 d D U P A 2
H2X H 0.673407 0.667363 0.023106 0.057 Uiso 0.298(11) 1 calc R U P A 2
C3X C 0.574(2) 0.6418(16) 0.1181(14) 0.043(6) Uiso 0.298(11) 1 d D U P A 2
H3X H 0.515910 0.675114 0.098875 0.051 Uiso 0.298(11) 1 calc R U P A 2
C4X C 0.5683(18) 0.6019(15) 0.1961(12) 0.038(5) Uiso 0.298(11) 1 d D U P A 2
N4X N 0.4917(17) 0.6216(16) 0.2510(13) 0.048(8) Uiso 0.298(11) 1 d D U P A 2
H4X1 H 0.490781 0.597826 0.300684 0.058 Uiso 0.298(11) 1 calc R U P A 2
H4X2 H 0.442183 0.658237 0.237516 0.058 Uiso 0.298(11) 1 calc R U P A 2
C5X C 0.648(2) 0.5438(18) 0.2158(13) 0.047(6) Uiso 0.298(11) 1 d D U P A 2
H5X H 0.646026 0.514867 0.267631 0.056 Uiso 0.298(11) 1 calc R U P A 2
C6X C 0.7294(19) 0.5285(17) 0.1605(15) 0.046(6) Uiso 0.298(11) 1 d D U P A 2
H6X H 0.780065 0.485924 0.172415 0.055 Uiso 0.298(11) 1 calc R U P A 2
N1Y N 0.032(2) 0.2753(17) 0.3510(18) 0.032(6) Uiso 0.239(12) 1 d D U P B 2
H1NY H -0.014253 0.262733 0.311146 0.039 Uiso 0.239(12) 1 calc R U P B 2
C2Y C 0.099(3) 0.339(2) 0.345(3) 0.035(6) Uiso 0.239(12) 1 d D U P B 2
H2Y H 0.095742 0.369287 0.293649 0.042 Uiso 0.239(12) 1 calc R U P B 2
C3Y C 0.170(4) 0.366(3) 0.400(3) 0.038(6) Uiso 0.239(12) 1 d . U P B 2
H3Y H 0.216460 0.412598 0.390029 0.046 Uiso 0.239(12) 1 calc R U P B 2
C4Y C 0.171(4) 0.319(3) 0.476(3) 0.034(5) Uiso 0.239(12) 1 d . U P B 2
N4Y N 0.237(3) 0.338(3) 0.537(3) 0.033(11) Uiso 0.239(12) 1 d . U P B 2
H4Y1 H 0.239707 0.306801 0.581994 0.039 Uiso 0.239(12) 1 calc R U P B 2
H4Y2 H 0.278718 0.382192 0.532367 0.039 Uiso 0.239(12) 1 calc R U P B 2
C5Y C 0.108(4) 0.248(3) 0.491(3) 0.036(6) Uiso 0.239(12) 1 d . U P B 2
H5Y H 0.112885 0.214795 0.539943 0.043 Uiso 0.239(12) 1 calc R U P B 2
C6Y C 0.039(3) 0.229(2) 0.425(2) 0.015(6) Uiso 0.239(12) 1 d . U P B 2
H6Y H -0.007106 0.182384 0.431512 0.018 Uiso 0.239(12) 1 calc R U P B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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 119.0(3) . . yes
O1A P1A O3A 106.7(3) . . yes
O2A P1A O3A 111.0(3) . . yes
O1A P1A P2A 108.5(3) . . yes
O2A P1A P2A 106.2(2) . . yes
O3A P1A P2A 104.5(2) . . yes
P1A O3A H3PA 109.5 . . ?
O4A P2A O5A 114.8(3) . . yes
O4A P2A O6A 107.7(3) . . yes
O5A P2A O6A 111.6(3) . . yes
O4A P2A P1A 110.1(3) . . yes
O5A P2A P1A 107.6(2) . . yes
O6A P2A P1A 104.6(2) . . yes
P2A O6A H6PA 109.5 . . ?
O1B P1B O2B 118.1(3) . . yes
O1B P1B O3B 111.9(3) . . yes
O2B P1B O3B 105.6(3) . . yes
O1B P1B P2B 107.6(2) . . yes
O2B P1B P2B 108.2(3) . . yes
O3B P1B P2B 104.6(2) . . yes
P1B O3B H3PB 109.5 . . ?
O4B P2B O5B 114.7(3) . . yes
O4B P2B O6B 107.5(3) . . yes
O5B P2B O6B 110.6(3) . . yes
O4B P2B P1B 111.1(2) . . yes
O5B P2B P1B 107.1(2) . . yes
O6B P2B P1B 105.4(2) . . yes
P2B O6B H6PB 109.5 . . ?
C6A N1A C2A 119.8(8) . . ?
C6A N1A H1NA 120.1 . . ?
C2A N1A H1NA 120.1 . . ?
C3A C2A N1A 121.4(10) . . ?
C3A C2A H2A 119.3 . . ?
N1A C2A H2A 119.3 . . ?
C2A C3A C4A 120.1(9) . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
N4A C4A C5A 123.3(8) . . ?
N4A C4A C3A 119.7(8) . . ?
C5A C4A C3A 117.0(8) . . ?
C4A N4A H4A1 120.0 . . ?
C4A N4A H4A2 120.0 . . ?
H4A1 N4A H4A2 120.0 . . ?
C6A C5A C4A 120.9(9) . . ?
C6A C5A H5A 119.6 . . ?
C4A C5A H5A 119.6 . . ?
N1A C6A C5A 120.9(9) . . ?
N1A C6A H6A 119.6 . . ?
C5A C6A H6A 119.6 . . ?
C2B N1B C6B 120.5(8) . . ?
C2B N1B H1NB 119.7 . . ?
C6B N1B H1NB 119.7 . . ?
N1B C2B C3B 122.1(9) . . ?
N1B C2B H2B 118.9 . . ?
C3B C2B H2B 118.9 . . ?
C2B C3B C4B 118.9(9) . . ?
C2B C3B H3B 120.5 . . ?
C4B C3B H3B 120.5 . . ?
N4B C4B C3B 122.6(8) . . ?
N4B C4B C5B 121.0(8) . . ?
C3B C4B C5B 116.4(8) . . ?
C4B N4B H4B1 120.0 . . ?
C4B N4B H4B2 120.0 . . ?
H4B1 N4B H4B2 120.0 . . ?
C6B C5B C4B 121.1(8) . . ?
C6B C5B H5B 119.5 . . ?
C4B C5B H5B 119.5 . . ?
N1B C6B C5B 120.8(9) . . ?
N1B C6B H6B 119.6 . . ?
C5B C6B H6B 119.6 . . ?
C6C N1C C2C 119.5(7) . . ?
C6C N1C H1NC 120.2 . . ?
C2C N1C H1NC 120.2 . . ?
C3C C2C N1C 121.6(9) . . ?
C3C C2C H2C 119.2 . . ?
N1C C2C H2C 119.2 . . ?
C2C C3C C4C 119.5(9) . . ?
C2C C3C H3C 120.3 . . ?
C4C C3C H3C 120.3 . . ?
N4C C4C C5C 121.3(7) . . ?
N4C C4C C3C 120.7(8) . . ?
C5C C4C C3C 117.9(8) . . ?
C4C N4C H4C1 120.0 . . ?
C4C N4C H4C2 120.0 . . ?
H4C1 N4C H4C2 120.0 . . ?
C6C C5C C4C 120.2(7) . . ?
C6C C5C H5C 119.9 . . ?
C4C C5C H5C 119.9 . . ?
N1C C6C C5C 121.0(8) . . ?
N1C C6C H6C 119.5 . . ?
C5C C6C H6C 119.5 . . ?
C2D N1D C6D 120.7(11) . . ?
C2D N1D H1ND 119.6 . . ?
C6D N1D H1ND 119.6 . . ?
N1D C2D C3D 121.2(12) . . ?
N1D C2D H2D 119.4 . . ?
C3D C2D H2D 119.4 . . ?
C2D C3D C4D 120.4(11) . . ?
C2D C3D H3D 119.8 . . ?
C4D C3D H3D 119.8 . . ?
N4D C4D C5D 122.6(11) . . ?
N4D C4D C3D 122.7(10) . . ?
C5D C4D C3D 114.7(10) . . ?
C4D N4D H4D1 120.0 . . ?
C4D N4D H4D2 120.0 . . ?
H4D1 N4D H4D2 120.0 . . ?
C6D C5D C4D 121.2(11) . . ?
C6D C5D H5D 119.4 . . ?
C4D C5D H5D 119.4 . . ?
C5D C6D N1D 121.8(14) . . ?
C5D C6D H6D 119.1 . . ?
N1D C6D H6D 119.1 . . ?
C6X N1X C2X 119.4(8) . . ?
C6X N1X H1NX 120.3 . . ?
C2X N1X H1NX 120.3 . . ?
C3X C2X N1X 121.3(10) . . ?
C3X C2X H2X 119.3 . . ?
N1X C2X H2X 119.3 . . ?
C2X C3X C4X 119.2(10) . . ?
C2X C3X H3X 120.4 . . ?
C4X C3X H3X 120.4 . . ?
N4X C4X C5X 121.4(8) . . ?
N4X C4X C3X 120.8(8) . . ?
C5X C4X C3X 117.8(9) . . ?
C4X N4X H4X1 120.0 . . ?
C4X N4X H4X2 120.0 . . ?
H4X1 N4X H4X2 120.0 . . ?
C6X C5X C4X 120.2(8) . . ?
C6X C5X H5X 119.9 . . ?
C4X C5X H5X 119.9 . . ?
N1X C6X C5X 121.0(8) . . ?
N1X C6X H6X 119.5 . . ?
C5X C6X H6X 119.5 . . ?
C2Y N1Y C6Y 115(3) . . ?
C2Y N1Y H1NY 122.3 . . ?
C6Y N1Y H1NY 122.3 . . ?
N1Y C2Y C3Y 129(4) . . ?
N1Y C2Y H2Y 115.5 . . ?
C3Y C2Y H2Y 115.5 . . ?
C2Y C3Y C4Y 113(4) . . ?
C2Y C3Y H3Y 123.4 . . ?
C4Y C3Y H3Y 123.4 . . ?
N4Y C4Y C5Y 115(4) . . ?
N4Y C4Y C3Y 121(5) . . ?
C5Y C4Y C3Y 124(4) . . ?
C4Y N4Y H4Y1 120.0 . . ?
C4Y N4Y H4Y2 120.0 . . ?
H4Y1 N4Y H4Y2 120.0 . . ?
C6Y C5Y C4Y 114(4) . . ?
C6Y C5Y H5Y 123.2 . . ?
C4Y C5Y H5Y 123.2 . . ?
C5Y C6Y N1Y 125(4) . . ?
C5Y C6Y H6Y 117.7 . . ?
N1Y C6Y H6Y 117.7 . . ?
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 1.490(6) . yes
P1A O2A 1.496(6) . yes
P1A O3A 1.583(5) . yes
P1A P2A 2.183(3) . yes
O3A H3PA 0.8400 . ?
P2A O4A 1.500(5) . yes
P2A O5A 1.514(5) . yes
P2A O6A 1.559(6) . yes
O6A H6PA 0.8400 . ?
P1B O1B 1.501(6) . yes
P1B O2B 1.510(6) . yes
P1B O3B 1.574(6) . yes
P1B P2B 2.181(3) . yes
O3B H3PB 0.8400 . ?
P2B O4B 1.504(5) . yes
P2B O5B 1.525(5) . yes
P2B O6B 1.576(5) . yes
O6B H6PB 0.8400 . ?
N1A C6A 1.350(12) . ?
N1A C2A 1.358(12) . ?
N1A H1NA 0.8800 . ?
C2A C3A 1.358(13) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.415(12) . ?
C3A H3A 0.9500 . ?
C4A N4A 1.344(11) . ?
C4A C5A 1.389(13) . ?
N4A H4A1 0.8800 . ?
N4A H4A2 0.8800 . ?
C5A C6A 1.370(12) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
N1B C2B 1.338(12) . ?
N1B C6B 1.339(12) . ?
N1B H1NB 0.8800 . ?
C2B C3B 1.360(13) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.414(11) . ?
C3B H3B 0.9500 . ?
C4B N4B 1.321(12) . ?
C4B C5B 1.417(12) . ?
N4B H4B1 0.8800 . ?
N4B H4B2 0.8800 . ?
C5B C6B 1.340(13) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
N1C C6C 1.349(9) . ?
N1C C2C 1.370(12) . ?
N1C H1NC 0.8800 . ?
C2C C3C 1.360(9) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.402(13) . ?
C3C H3C 0.9500 . ?
C4C N4C 1.336(10) . ?
C4C C5C 1.400(10) . ?
N4C H4C1 0.8800 . ?
N4C H4C2 0.8800 . ?
C5C C6C 1.367(12) . ?
C5C H5C 0.9500 . ?
C6C H6C 0.9500 . ?
N1D C2D 1.326(10) . ?
N1D C6D 1.344(18) . ?
N1D H1ND 0.8800 . ?
C2D C3D 1.348(16) . ?
C2D H2D 0.9500 . ?
C3D C4D 1.438(16) . ?
C3D H3D 0.9500 . ?
C4D N4D 1.315(14) . ?
C4D C5D 1.421(15) . ?
N4D H4D1 0.8800 . ?
N4D H4D2 0.8800 . ?
C5D C6D 1.32(2) . ?
C5D H5D 0.9500 . ?
C6D H6D 0.9500 . ?
N1X C6X 1.349(10) . ?
N1X C2X 1.371(12) . ?
N1X H1NX 0.8800 . ?
C2X C3X 1.361(9) . ?
C2X H2X 0.9500 . ?
C3X C4X 1.402(13) . ?
C3X H3X 0.9500 . ?
C4X N4X 1.336(10) . ?
C4X C5X 1.400(10) . ?
N4X H4X1 0.8800 . ?
N4X H4X2 0.8800 . ?
C5X C6X 1.368(12) . ?
C5X H5X 0.9500 . ?
C6X H6X 0.9500 . ?
N1Y C2Y 1.326(10) . ?
N1Y C6Y 1.40(5) . ?
N1Y H1NY 0.8800 . ?
C2Y C3Y 1.33(6) . ?
C2Y H2Y 0.9500 . ?
C3Y C4Y 1.43(6) . ?
C3Y H3Y 0.9500 . ?
C4Y N4Y 1.31(6) . ?
C4Y C5Y 1.41(6) . ?
N4Y H4Y1 0.8800 . ?
N4Y H4Y2 0.8800 . ?
C5Y C6Y 1.39(6) . ?
C5Y H5Y 0.9500 . ?
C6Y H6Y 0.9500 . ?
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
O3A H3PA O4B 0.84 1.85 2.607(8) 148.6 .
O6A H6PA O5B 0.84 1.77 2.565(8) 158.0 .
O3B H3PB O4A 0.84 1.81 2.584(8) 152.8 4_466
O6B H6PB O5A 0.84 1.75 2.555(8) 158.8 4_466
N1A H1NA O5A 0.88 1.88 2.721(9) 159.8 .
C2A H2A O6A 0.95 2.23 2.981(11) 135.1 4_566
N4A H4A1 O4A 0.88 2.20 3.014(9) 154.4 2_664
N4A H4A2 O1B 0.88 2.06 2.944(9) 176.3 1_655
C5A H5A O3B 0.95 2.44 3.287(11) 147.7 3_645
C6A H6A O1A 0.95 2.51 3.262(10) 136.6 .
N1B H1NB O5B 0.88 1.91 2.729(9) 154.0 .
C2B H2B O6B 0.95 2.38 3.093(10) 131.5 4_566
N4B H4B1 O2A 0.88 2.04 2.910(9) 171.4 4_566
N4B H4B2 O4B 0.88 2.17 2.988(9) 155.1 3_655
C5B H5B O3A 0.95 2.56 3.338(10) 139.8 3_655
C6B H6B O2B 0.95 2.49 3.208(12) 132.4 .
N1C H1NC O2B 0.88 1.73 2.606(9) 170.4 .
N4C H4C1 O3B 0.88 2.20 3.075(10) 170.4 3_645
N4C H4C2 O1A 0.88 2.01 2.878(10) 167.1 2_664
C6C H6C O3A 0.95 2.61 3.369(11) 137.5 .
N1X H1NX O1A 0.88 1.74 2.592(17) 163.7 2_664
N4X H4X1 O3A 0.88 2.16 3.03(2) 170.2 .
N4X H4X2 O2B 0.88 2.01 2.88(2) 176.2 .
C6X H6X O3B 0.95 2.64 3.44(2) 142.4 3_645
N1D H1ND O2A 0.88 1.93 2.697(9) 144.8 .
C2D H2D O4B 0.95 2.61 3.348(13) 135.0 .
N4D H4D2 O1B 0.88 1.90 2.755(11) 163.1 3_545
N4D H4D1 O1A 0.88 2.10 2.934(12) 157.2 4_456
N1Y H1NY O1B 0.88 1.93 2.68(3) 142.0 3_545
C2Y H2Y O4A 0.95 2.61 3.39(4) 139.9 2_564
N4Y H4Y1 O1B 0.88 2.58 3.25(4) 133.1 2_565
N4Y H4Y1 O2B 0.88 2.23 3.03(5) 151.0 2_565
N4Y H4Y2 O2A 0.88 1.97 2.83(5) 166.7 .
C6Y H6Y O1A 0.95 2.58 3.12(4) 116.4 4_456
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
O1A P1A P2A O4A -69.9(4) . . . . yes
O2A P1A P2A O4A 59.1(4) . . . . yes
O3A P1A P2A O4A 176.5(3) . . . . yes
O1A P1A P2A O5A 56.0(3) . . . . yes
O2A P1A P2A O5A -175.1(3) . . . . yes
O3A P1A P2A O5A -57.6(3) . . . . yes
O1A P1A P2A O6A 174.7(3) . . . . yes
O2A P1A P2A O6A -56.3(3) . . . . yes
O3A P1A P2A O6A 61.1(3) . . . . yes
O1B P1B P2B O4B 53.9(4) . . . . yes
O2B P1B P2B O4B -74.8(4) . . . . yes
O3B P1B P2B O4B 173.0(3) . . . . yes
O1B P1B P2B O5B 180.0(4) . . . . yes
O2B P1B P2B O5B 51.3(4) . . . . yes
O3B P1B P2B O5B -60.9(3) . . . . yes
O1B P1B P2B O6B -62.2(4) . . . . yes
O2B P1B P2B O6B 169.1(3) . . . . yes
O3B P1B P2B O6B 56.9(3) . . . . yes
C6A N1A C2A C3A 0.0(17) . . . . ?
N1A C2A C3A C4A 0.6(17) . . . . ?
C2A C3A C4A N4A 179.1(10) . . . . ?
C2A C3A C4A C5A -0.9(15) . . . . ?
N4A C4A C5A C6A -179.4(9) . . . . ?
C3A C4A C5A C6A 0.6(15) . . . . ?
C2A N1A C6A C5A -0.4(17) . . . . ?
C4A C5A C6A N1A 0.1(17) . . . . ?
C6B N1B C2B C3B 1.5(17) . . . . ?
N1B C2B C3B C4B 2.2(17) . . . . ?
C2B C3B C4B N4B 174.8(10) . . . . ?
C2B C3B C4B C5B -4.3(15) . . . . ?
N4B C4B C5B C6B -176.1(10) . . . . ?
C3B C4B C5B C6B 3.1(15) . . . . ?
C2B N1B C6B C5B -2.9(17) . . . . ?
C4B C5B C6B N1B 0.5(17) . . . . ?
C6C N1C C2C C3C 2.1(18) . . . . ?
N1C C2C C3C C4C 1(2) . . . . ?
C2C C3C C4C N4C 179.9(13) . . . . ?
C2C C3C C4C C5C -4(2) . . . . ?
N4C C4C C5C C6C -179.4(13) . . . . ?
C3C C4C C5C C6C 4(2) . . . . ?
C2C N1C C6C C5C -1.7(19) . . . . ?
C4C C5C C6C N1C -2(2) . . . . ?
C6D N1D C2D C3D -0.8(17) . . . . ?
N1D C2D C3D C4D 0.4(18) . . . . ?
C2D C3D C4D N4D -179.8(11) . . . . ?
C2D C3D C4D C5D 0.6(17) . . . . ?
N4D C4D C5D C6D 179.2(12) . . . . ?
C3D C4D C5D C6D -1.2(17) . . . . ?
C4D C5D C6D N1D 1(2) . . . . ?
C2D N1D C6D C5D 0(2) . . . . ?
C6X N1X C2X C3X -6(5) . . . . ?
N1X C2X C3X C4X 12(4) . . . . ?
C2X C3X C4X N4X 168(3) . . . . ?
C2X C3X C4X C5X -10(4) . . . . ?
N4X C4X C5X C6X -176(3) . . . . ?
C3X C4X C5X C6X 1(5) . . . . ?
C2X N1X C6X C5X -3(5) . . . . ?
C4X C5X C6X N1X 5(5) . . . . ?
C6Y N1Y C2Y C3Y -2(6) . . . . ?
N1Y C2Y C3Y C4Y -1(7) . . . . ?
C2Y C3Y C4Y N4Y 180(4) . . . . ?
C2Y C3Y C4Y C5Y 4(6) . . . . ?
N4Y C4Y C5Y C6Y 180(4) . . . . ?
C3Y C4Y C5Y C6Y -4(6) . . . . ?
C4Y C5Y C6Y N1Y 2(6) . . . . ?
C2Y N1Y C6Y C5Y 1(5) . . . . ?
