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The present paper reports the structures of bis­(adeninium) zoledronate tetra­hydrate {systematic name: bis(6-amino-7H-purin-1-ium) hydrogen [1-hy­droxy-2-(1H-imidazol-3-ium-1-yl)-1-phospho­natoeth­yl]phospho­nate tetra­hydrate}, 2C5H6N5+·C5H8N2O7P22-·4H2O, (I), and bis­(ade­ninium) zoledron­ate hexa­hydrate {systematic name: a 1:1 cocrystal of bis(6-amino-7H-purin-1-ium) ­hydrogen [1-hy­droxy-2-(1H-imidazol-3-ium-1-yl)-1-phos­pho­natoeth­yl]phospho­nate hexa­hydrate and 6-amino-7H-purin-1-ium 6-amino-7H-purine di­hydrogen [1-hy­droxy-2-(1H-imidazol-3-ium-1-yl)ethane-1,1-diyl]diphos­pho­nate hexa­hydrate}, 2C5H6N5+·C5H8N2O7P22-·6H2O, (II). One of the adenine mol­e­cules and one of the phospho­nate groups of the zole­dronate anion of (II) are protonated on a 50% basis. The zoledronate group displays its usual zwitterionic character, with a protonated imidazole ring; however, the ionization state of the phospho­nate groups of the anion for (I) and (II) are different. In (I), the anion has both singly and doubly deprotonated phospho­nate groups, while in (II), it has one singly deprotonated phospho­nate group and a partially deprotonated phospho­nate group. In (I), the cations form an R22(10) base pair, while in (II), they form R22(8) and R22(10) base pairs. Two water mol­ecules in (I) and five water mol­ecules in (II) are involved in water-water inter­actions. The presence of an additional two water mol­ecules in the structure of (II) might influence the different ionization state of the anion as well as the different packing mode compared to (I).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229613033172/sf3214sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229613033172/sf3214Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229613033172/sf3214Isup4.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229613033172/sf3214IIsup3.hkl
Contains datablock ar34m

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229613033172/sf3214IIsup5.cml
Supplementary material

CCDC references: 896639; 975728

Computing details top

For both compounds, data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

(I) Bis(6-amino-7H-purin-1-ium) hydrogen [1-hydroxy-2-(1H-imidazol-3-ium-1-yl)-1-phosphonatoethyl]phosphonate tetrahydrate top
Crystal data top
2C5H6N5+·C5H8N2O7P22·4H2OF(000) = 1280
Mr = 614.43Dx = 1.648 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5448 reflections
a = 7.2128 (7) Åθ = 2.4–27.7°
b = 17.7448 (17) ŵ = 0.26 mm1
c = 19.3945 (18) ÅT = 294 K
β = 93.999 (2)°Block, colorless
V = 2476.3 (4) Å30.19 × 0.16 × 0.07 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5901 independent reflections
Radiation source: fine-focus sealed tube5410 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω scanθmax = 28.0°, θmin = 1.6°
Absorption correction: multi-scan
(SABABS; Bruker, 2001)
h = 99
Tmin = 0.93, Tmax = 0.98k = 2323
28416 measured reflectionsl = 2525
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.15 w = 1/[σ2(Fo2) + (0.0531P)2 + 2.9198P]
where P = (Fo2 + 2Fc2)/3
5901 reflections(Δ/σ)max = 0.001
439 parametersΔρmax = 0.75 e Å3
23 restraintsΔρmin = 0.42 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C2A0.5260 (4)0.25330 (18)0.07844 (15)0.0435 (7)
H2A0.49940.21150.10630.052*
C4A0.5302 (3)0.31295 (16)0.02134 (14)0.0341 (6)
C5A0.6097 (3)0.37845 (16)0.00415 (13)0.0331 (5)
C6A0.6491 (3)0.37961 (15)0.07343 (14)0.0332 (5)
C8A0.5755 (4)0.39843 (17)0.10047 (15)0.0403 (6)
H8A0.57550.42150.14350.048*
N1A0.6051 (3)0.31278 (15)0.10796 (12)0.0387 (5)
H1A0.636 (5)0.306 (2)0.1516 (11)0.065 (11)*
N3A0.4832 (3)0.24907 (15)0.01402 (12)0.0415 (6)
N7A0.6384 (3)0.43184 (13)0.04610 (12)0.0360 (5)
N9A0.5109 (3)0.32759 (14)0.08845 (12)0.0358 (5)
H9A0.465 (5)0.2984 (19)0.1210 (16)0.064 (11)*
N10A0.7236 (3)0.43561 (13)0.10584 (12)0.0342 (5)
H10A0.758 (4)0.4769 (13)0.0847 (15)0.041 (9)*
H10B0.742 (5)0.432 (2)0.1500 (10)0.056 (10)*
C2B0.9969 (4)0.76027 (17)0.06231 (14)0.0400 (6)
H2B1.02560.80200.09000.048*
C4B0.9816 (3)0.70141 (14)0.03749 (13)0.0301 (5)
C5B0.9081 (3)0.63592 (14)0.01097 (13)0.0299 (5)
C6B0.8790 (3)0.63405 (15)0.05976 (13)0.0301 (5)
C8B0.9384 (4)0.61454 (16)0.11626 (14)0.0356 (6)
H8B0.93610.59120.15930.043*
N1B0.9297 (3)0.69932 (14)0.09376 (11)0.0354 (5)
H1B0.925 (4)0.7015 (18)0.1399 (9)0.041 (8)*
N3B1.0256 (3)0.76644 (13)0.00340 (12)0.0384 (5)
N7B0.8811 (3)0.58140 (12)0.06098 (11)0.0329 (5)
N9B1.0012 (3)0.68584 (13)0.10488 (11)0.0338 (5)
H9B1.037 (5)0.7174 (17)0.1361 (15)0.055 (10)*
N10B0.8096 (3)0.57685 (14)0.09271 (12)0.0365 (5)
H10C0.811 (5)0.577 (2)0.1384 (10)0.050 (9)*
H10D0.775 (4)0.5369 (13)0.0702 (14)0.037 (8)*
C121.1858 (4)0.57213 (16)0.49525 (12)0.0330 (5)
H121.14320.61960.50700.040*
C141.2700 (4)0.45392 (17)0.50172 (14)0.0391 (6)
H141.29470.40580.51910.047*
C151.2933 (4)0.47780 (15)0.43687 (14)0.0345 (6)
H151.33760.44950.40120.041*
C161.2436 (3)0.60388 (14)0.37435 (12)0.0286 (5)
H16A1.33760.58630.34480.034*
H16B1.28170.65320.39150.034*
C171.0595 (3)0.61235 (12)0.33032 (11)0.0223 (4)
O180.9207 (2)0.63287 (11)0.37640 (9)0.0309 (4)
H180.820 (4)0.649 (2)0.3548 (19)0.071 (13)*
O190.9351 (3)0.46788 (10)0.33925 (9)0.0382 (4)
O201.1339 (3)0.50032 (11)0.24013 (11)0.0407 (5)
O210.8067 (3)0.54653 (11)0.23936 (9)0.0349 (4)
H210.707 (4)0.528 (2)0.254 (2)0.073 (13)*
O221.1557 (3)0.75892 (10)0.31491 (9)0.0332 (4)
O230.9200 (2)0.70529 (10)0.22666 (9)0.0310 (4)
O241.2601 (2)0.66607 (10)0.22820 (9)0.0329 (4)
N111.2389 (3)0.55209 (12)0.43374 (10)0.0287 (4)
N131.2035 (3)0.51335 (14)0.53708 (11)0.0370 (5)
H131.168 (6)0.514 (2)0.5801 (12)0.075 (13)*
P10.98661 (8)0.52422 (3)0.28594 (3)0.02453 (15)
P21.10190 (8)0.69171 (3)0.27012 (3)0.02273 (14)
O1W1.1037 (3)0.79444 (14)0.20060 (11)0.0476 (5)
H1W1.180 (4)0.789 (2)0.2318 (15)0.057*
H2W1.003 (4)0.806 (2)0.2242 (17)0.057*
O2W0.5014 (3)0.48671 (16)0.2722 (2)0.0762 (9)
H3W0.529 (7)0.4410 (14)0.282 (2)0.091*
H4W0.387 (3)0.495 (3)0.261 (2)0.091*
O3W1.1906 (6)0.33913 (17)0.30286 (18)0.0978 (12)
H5W1.227 (8)0.323 (3)0.2646 (17)0.117*
H6W1.147 (8)0.3829 (17)0.295 (3)0.117*
O4W0.6643 (6)0.3566 (2)0.3184 (3)0.0682 (14)0.790 (11)
O4W'0.690 (2)0.3578 (8)0.2672 (12)0.073 (4)0.210 (11)
H7W0.758 (7)0.374 (3)0.317 (3)0.087*
H8W0.664 (7)0.321 (3)0.289 (3)0.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C2A0.0408 (15)0.0500 (17)0.0397 (15)0.0031 (13)0.0025 (12)0.0041 (13)
C4A0.0237 (11)0.0427 (15)0.0358 (13)0.0012 (10)0.0024 (10)0.0119 (11)
C5A0.0288 (12)0.0400 (14)0.0305 (12)0.0028 (10)0.0023 (10)0.0037 (10)
C6A0.0253 (12)0.0376 (13)0.0369 (13)0.0048 (10)0.0033 (10)0.0071 (11)
C8A0.0431 (15)0.0439 (16)0.0345 (14)0.0022 (12)0.0064 (11)0.0039 (12)
N1A0.0345 (12)0.0557 (15)0.0265 (11)0.0001 (10)0.0067 (9)0.0022 (10)
N3A0.0355 (12)0.0562 (15)0.0336 (12)0.0024 (11)0.0078 (9)0.0063 (11)
N7A0.0368 (12)0.0340 (12)0.0373 (12)0.0013 (9)0.0028 (9)0.0014 (9)
N9A0.0340 (11)0.0407 (13)0.0334 (12)0.0009 (10)0.0064 (9)0.0094 (10)
N10A0.0396 (12)0.0346 (12)0.0292 (11)0.0018 (10)0.0099 (9)0.0063 (9)
C2B0.0418 (15)0.0415 (15)0.0357 (14)0.0014 (12)0.0051 (11)0.0082 (12)
C4B0.0264 (11)0.0341 (13)0.0292 (12)0.0040 (10)0.0016 (9)0.0053 (10)
C5B0.0282 (12)0.0327 (12)0.0284 (12)0.0037 (10)0.0018 (9)0.0004 (10)
C6B0.0252 (11)0.0361 (13)0.0287 (12)0.0045 (10)0.0014 (9)0.0011 (10)
C8B0.0388 (14)0.0390 (14)0.0290 (12)0.0031 (11)0.0011 (10)0.0010 (11)
N1B0.0374 (12)0.0454 (13)0.0228 (10)0.0035 (10)0.0018 (9)0.0045 (9)
N3B0.0410 (13)0.0395 (12)0.0342 (12)0.0002 (10)0.0001 (10)0.0005 (10)
N7B0.0352 (11)0.0328 (11)0.0302 (11)0.0001 (9)0.0001 (9)0.0027 (9)
N9B0.0354 (11)0.0374 (12)0.0286 (11)0.0022 (9)0.0014 (9)0.0052 (9)
N10B0.0403 (12)0.0423 (13)0.0269 (11)0.0032 (10)0.0029 (9)0.0046 (10)
C120.0335 (13)0.0397 (14)0.0253 (12)0.0049 (11)0.0003 (10)0.0016 (10)
C140.0374 (14)0.0407 (15)0.0382 (14)0.0021 (11)0.0032 (11)0.0124 (12)
C150.0355 (13)0.0341 (13)0.0335 (13)0.0016 (11)0.0003 (10)0.0028 (10)
C160.0304 (12)0.0313 (12)0.0237 (11)0.0072 (10)0.0008 (9)0.0047 (9)
C170.0263 (11)0.0209 (10)0.0201 (10)0.0024 (8)0.0046 (8)0.0009 (8)
O180.0311 (9)0.0406 (10)0.0220 (8)0.0018 (8)0.0095 (7)0.0000 (7)
O190.0523 (12)0.0298 (9)0.0314 (9)0.0109 (8)0.0042 (8)0.0068 (7)
O200.0370 (10)0.0371 (10)0.0488 (12)0.0016 (8)0.0093 (9)0.0164 (9)
O210.0308 (9)0.0418 (10)0.0312 (9)0.0108 (8)0.0045 (7)0.0089 (8)
O220.0409 (10)0.0267 (9)0.0327 (9)0.0048 (7)0.0059 (8)0.0045 (7)
O230.0330 (9)0.0325 (9)0.0274 (8)0.0013 (7)0.0010 (7)0.0034 (7)
O240.0354 (9)0.0332 (9)0.0317 (9)0.0021 (7)0.0144 (7)0.0028 (7)
N110.0291 (10)0.0337 (11)0.0229 (9)0.0045 (8)0.0011 (8)0.0026 (8)
N130.0375 (12)0.0491 (14)0.0243 (11)0.0065 (10)0.0005 (9)0.0072 (10)
P10.0271 (3)0.0237 (3)0.0227 (3)0.0033 (2)0.0010 (2)0.0007 (2)
P20.0269 (3)0.0216 (3)0.0202 (3)0.0008 (2)0.0052 (2)0.0001 (2)
O1W0.0341 (11)0.0693 (15)0.0399 (11)0.0011 (10)0.0069 (9)0.0120 (10)
O2W0.0323 (12)0.0626 (17)0.135 (3)0.0018 (12)0.0169 (15)0.0283 (18)
O3W0.170 (4)0.0441 (15)0.086 (2)0.0370 (19)0.059 (2)0.0103 (15)
O4W0.068 (2)0.0411 (18)0.096 (4)0.0219 (16)0.007 (2)0.0019 (19)
O4W'0.071 (7)0.042 (6)0.104 (9)0.013 (5)0.007 (7)0.002 (7)
Geometric parameters (Å, º) top
C2A—N3A1.310 (4)C12—N131.322 (3)
C2A—N1A1.346 (4)C12—N111.327 (3)
C2A—H2A0.9300C12—H120.9300
C4A—N9A1.344 (4)C14—C151.349 (4)
C4A—N3A1.356 (4)C14—N131.363 (4)
C4A—C5A1.401 (4)C14—H140.9300
C5A—N7A1.365 (3)C15—N111.376 (3)
C5A—C6A1.393 (4)C15—H150.9300
C6A—N10A1.311 (3)C16—N111.476 (3)
C6A—N1A1.388 (4)C16—C171.535 (3)
C8A—N7A1.318 (4)C16—H16A0.9700
C8A—N9A1.355 (4)C16—H16B0.9700
C8A—H8A0.9300C17—O181.435 (3)
N1A—H1A0.898 (18)C17—P11.844 (2)
N9A—H9A0.896 (18)C17—P21.868 (2)
N10A—H10A0.867 (18)O18—H180.857 (19)
N10A—H10B0.879 (18)O19—P11.5033 (18)
C2B—N3B1.310 (4)O20—P11.4931 (19)
C2B—N1B1.349 (4)O21—P11.5792 (19)
C2B—H2B0.9300O21—H210.859 (19)
C4B—N9B1.353 (3)O22—P21.5101 (18)
C4B—N3B1.356 (3)O23—P21.5282 (18)
C4B—C5B1.391 (4)O24—P21.5167 (17)
C5B—N7B1.374 (3)N13—H130.889 (19)
C5B—C6B1.402 (3)O1W—H1W0.852 (18)
C6B—N10B1.317 (3)O1W—H2W0.861 (18)
C6B—N1B1.370 (3)O2W—H3W0.852 (19)
C8B—N7B1.314 (3)O2W—H4W0.853 (19)
C8B—N9B1.357 (4)O3W—H5W0.85 (2)
C8B—H8B0.9300O3W—H6W0.85 (2)
N1B—H1B0.899 (18)O4W—H7W0.75 (5)
N9B—H9B0.877 (18)O4W—H8W0.86 (5)
N10B—H10C0.885 (18)O4W'—H7W1.10 (5)
N10B—H10D0.860 (18)O4W'—H8W0.81 (5)
N3A—C2A—N1A125.8 (3)C6B—N10B—H10C121 (2)
N3A—C2A—H2A117.1C6B—N10B—H10D120 (2)
N1A—C2A—H2A117.1H10C—N10B—H10D119 (3)
N9A—C4A—N3A127.7 (2)N13—C12—N11108.6 (2)
N9A—C4A—C5A104.7 (2)N13—C12—H12125.7
N3A—C4A—C5A127.5 (2)N11—C12—H12125.7
N7A—C5A—C6A130.4 (3)C15—C14—N13107.3 (2)
N7A—C5A—C4A111.7 (2)C15—C14—H14126.4
C6A—C5A—C4A118.0 (3)N13—C14—H14126.4
N10A—C6A—N1A120.3 (2)C14—C15—N11106.8 (2)
N10A—C6A—C5A126.3 (3)C14—C15—H15126.6
N1A—C6A—C5A113.4 (2)N11—C15—H15126.6
N7A—C8A—N9A114.4 (3)N11—C16—C17115.42 (19)
N7A—C8A—H8A122.8N11—C16—H16A108.4
N9A—C8A—H8A122.8C17—C16—H16A108.4
C2A—N1A—C6A123.6 (2)N11—C16—H16B108.4
C2A—N1A—H1A116 (3)C17—C16—H16B108.4
C6A—N1A—H1A120 (3)H16A—C16—H16B107.5
C2A—N3A—C4A111.5 (3)O18—C17—C16107.01 (18)
C8A—N7A—C5A102.4 (2)O18—C17—P1108.49 (15)
C4A—N9A—C8A106.7 (2)C16—C17—P1112.59 (16)
C4A—N9A—H9A130 (3)O18—C17—P2110.47 (15)
C8A—N9A—H9A124 (3)C16—C17—P2104.40 (14)
C6A—N10A—H10A122 (2)P1—C17—P2113.66 (11)
C6A—N10A—H10B120 (2)C17—O18—H18112 (3)
H10A—N10A—H10B118 (3)P1—O21—H21113 (3)
N3B—C2B—N1B126.4 (3)C12—N11—C15108.4 (2)
N3B—C2B—H2B116.8C12—N11—C16124.0 (2)
N1B—C2B—H2B116.8C15—N11—C16127.5 (2)
N9B—C4B—N3B127.4 (2)C12—N13—C14108.9 (2)
N9B—C4B—C5B104.8 (2)C12—N13—H13122 (3)
N3B—C4B—C5B127.8 (2)C14—N13—H13128 (3)
N7B—C5B—C4B111.5 (2)O20—P1—O19116.14 (12)
N7B—C5B—C6B130.6 (2)O20—P1—O21108.74 (11)
C4B—C5B—C6B117.9 (2)O19—P1—O21109.12 (11)
N10B—C6B—N1B121.0 (2)O20—P1—C17109.09 (11)
N10B—C6B—C5B125.5 (2)O19—P1—C17108.61 (10)
N1B—C6B—C5B113.4 (2)O21—P1—C17104.52 (11)
N7B—C8B—N9B113.9 (2)O22—P2—O24111.88 (11)
N7B—C8B—H8B123.1O22—P2—O23111.64 (10)
N9B—C8B—H8B123.1O24—P2—O23113.63 (10)
C2B—N1B—C6B123.5 (2)O22—P2—C17106.41 (10)
C2B—N1B—H1B117 (2)O24—P2—C17105.72 (10)
C6B—N1B—H1B119 (2)O23—P2—C17106.99 (10)
C2B—N3B—C4B110.8 (2)H1W—O1W—H2W103 (3)
C8B—N7B—C5B102.9 (2)H3W—O2W—H4W115 (5)
C4B—N9B—C8B106.9 (2)H5W—O3W—H6W106 (5)
C4B—N9B—H9B126 (2)H7W—O4W—H8W104 (5)
C8B—N9B—H9B126 (2)H7W—O4W'—H8W82 (5)
N9A—C4A—C5A—N7A0.1 (3)C4B—C5B—N7B—C8B0.1 (3)
N3A—C4A—C5A—N7A180.0 (2)C6B—C5B—N7B—C8B177.8 (3)
N9A—C4A—C5A—C6A179.1 (2)N3B—C4B—N9B—C8B179.6 (3)
N3A—C4A—C5A—C6A1.0 (4)C5B—C4B—N9B—C8B0.9 (3)
N7A—C5A—C6A—N10A1.0 (5)N7B—C8B—N9B—C4B1.0 (3)
C4A—C5A—C6A—N10A179.8 (2)N13—C14—C15—N110.4 (3)
N7A—C5A—C6A—N1A177.8 (3)N11—C16—C17—O1853.9 (3)
C4A—C5A—C6A—N1A1.0 (3)N11—C16—C17—P165.2 (2)
N3A—C2A—N1A—C6A1.4 (5)N11—C16—C17—P2171.07 (17)
N10A—C6A—N1A—C2A179.0 (3)N13—C12—N11—C150.3 (3)
C5A—C6A—N1A—C2A2.2 (4)N13—C12—N11—C16178.0 (2)
N1A—C2A—N3A—C4A0.6 (4)C14—C15—N11—C120.4 (3)
N9A—C4A—N3A—C2A178.3 (3)C14—C15—N11—C16178.1 (2)
C5A—C4A—N3A—C2A1.8 (4)C17—C16—N11—C1285.5 (3)
N9A—C8A—N7A—C5A0.6 (3)C17—C16—N11—C1597.2 (3)
C6A—C5A—N7A—C8A179.3 (3)N11—C12—N13—C140.1 (3)
C4A—C5A—N7A—C8A0.4 (3)C15—C14—N13—C120.2 (3)
N3A—C4A—N9A—C8A179.6 (3)O18—C17—P1—O20177.50 (15)
C5A—C4A—N9A—C8A0.3 (3)C16—C17—P1—O2059.26 (18)
N7A—C8A—N9A—C4A0.6 (3)P2—C17—P1—O2059.20 (15)
N9B—C4B—C5B—N7B0.6 (3)O18—C17—P1—O1950.03 (18)
N3B—C4B—C5B—N7B179.9 (2)C16—C17—P1—O1968.21 (18)
N9B—C4B—C5B—C6B177.5 (2)P2—C17—P1—O19173.33 (12)
N3B—C4B—C5B—C6B1.9 (4)O18—C17—P1—O2166.34 (16)
N7B—C5B—C6B—N10B2.8 (4)C16—C17—P1—O21175.41 (15)
C4B—C5B—C6B—N10B179.5 (2)P2—C17—P1—O2156.96 (14)
N7B—C5B—C6B—N1B177.5 (2)O18—C17—P2—O2256.58 (17)
C4B—C5B—C6B—N1B0.2 (3)C16—C17—P2—O2258.14 (17)
N3B—C2B—N1B—C6B0.8 (5)P1—C17—P2—O22178.79 (12)
N10B—C6B—N1B—C2B178.2 (3)O18—C17—P2—O24175.69 (15)
C5B—C6B—N1B—C2B1.5 (4)C16—C17—P2—O2460.96 (17)
N1B—C2B—N3B—C4B1.2 (4)P1—C17—P2—O2462.10 (14)
N9B—C4B—N3B—C2B176.8 (3)O18—C17—P2—O2362.89 (17)
C5B—C4B—N3B—C2B2.6 (4)C16—C17—P2—O23177.61 (15)
N9B—C8B—N7B—C5B0.5 (3)P1—C17—P2—O2359.33 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O24i0.90 (2)1.78 (2)2.615 (3)154 (4)
N9A—H9A···O22ii0.90 (2)1.72 (2)2.599 (3)167 (4)
N10A—H10A···N7B0.87 (2)2.09 (2)2.933 (3)163 (3)
N10A—H10B···O24i0.88 (2)2.31 (3)2.990 (3)135 (3)
N10A—H10B···O20i0.88 (2)2.35 (3)3.083 (3)141 (3)
N1B—H1B···O230.90 (2)1.69 (2)2.585 (3)179 (3)
N9B—H9B···O1W0.88 (2)1.94 (2)2.810 (3)174 (3)
N10B—H10C···O210.89 (2)2.03 (2)2.896 (3)165 (3)
N10B—H10D···N7A0.86 (2)2.15 (2)2.968 (3)160 (3)
O18—H18···O1Wiii0.86 (2)2.09 (2)2.940 (3)169 (4)
O21—H21···O2W0.86 (2)1.71 (2)2.564 (3)172 (4)
N13—H13···O19iv0.89 (2)1.81 (2)2.683 (3)168 (4)
O1W—H1W···O23v0.85 (2)1.96 (2)2.765 (3)156 (4)
O1W—H2W···O24vi0.86 (2)1.98 (2)2.839 (3)176 (4)
O2W—H3W···O4W0.85 (2)1.91 (3)2.665 (15)147 (5)
O2W—H3W···O4W0.85 (2)1.90 (3)2.714 (5)159 (5)
O2W—H4W···O20vii0.85 (2)1.84 (2)2.691 (3)172 (5)
O3W—H5W···O22viii0.85 (2)2.14 (2)2.971 (3)165 (6)
O3W—H6W···O200.85 (2)2.34 (3)3.124 (4)155 (5)
O3W—H6W···O190.85 (2)2.35 (4)3.049 (4)139 (5)
O4W—H7W···O190.75 (5)2.13 (5)2.787 (4)148 (5)
O4W—H8W···O23ii0.85 (5)2.16 (5)2.876 (4)142 (5)
Symmetry codes: (i) x+2, y+1, z; (ii) x+3/2, y1/2, z+1/2; (iii) x1/2, y+3/2, z+1/2; (iv) x+2, y+1, z+1; (v) x+1/2, y+3/2, z1/2; (vi) x1/2, y+3/2, z1/2; (vii) x1, y, z; (viii) x+5/2, y1/2, z+1/2.
(II) Bis(6-amino-7H-purin-1-ium) hydrogen [1-hydroxy-2-(1H-imidazol-3-ium-1-yl)-1-phosphonatoethyl]phosphonate hexahydrate top
Crystal data top
2C5H6N5+·C5H8N2O7P22·6H2OZ = 2
Mr = 614.43F(000) = 680
Triclinic, P1Dx = 1.607 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2742 (6) ÅCell parameters from 5381 reflections
b = 10.7987 (9) Åθ = 2.5–27.8°
c = 17.6202 (15) ŵ = 0.25 mm1
α = 102.380 (1)°T = 294 K
β = 94.254 (1)°Needle, colourless
γ = 93.223 (1)°0.21 × 0.11 × 0.07 mm
V = 1344.49 (19) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
6286 independent reflections
Radiation source: fine-focus sealed tube5401 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ω scanθmax = 28.0°, θmin = 1.2°
Absorption correction: multi-scan
(SABABS; Bruker, 2001)
h = 99
Tmin = 0.96, Tmax = 0.99k = 1414
15899 measured reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.0651P)2 + 0.7724P]
where P = (Fo2 + 2Fc2)/3
6286 reflections(Δ/σ)max = 0.001
478 parametersΔρmax = 0.54 e Å3
44 restraintsΔρmin = 0.26 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C2A0.7027 (4)0.7288 (3)0.67916 (16)0.0389 (6)
H2A0.73230.70150.72480.047*
C4A0.6641 (4)0.6977 (2)0.55138 (14)0.0318 (5)
C5A0.6084 (3)0.8184 (2)0.55255 (14)0.0297 (5)
C6A0.6055 (3)0.9023 (2)0.62518 (14)0.0294 (5)
C8A0.6090 (4)0.7271 (3)0.43473 (16)0.0427 (7)
H8A0.59790.71070.38050.051*
N1A0.6532 (3)0.8490 (2)0.68685 (12)0.0338 (5)
H1A0.651 (4)0.892 (3)0.7336 (12)0.047 (9)*
N3A0.7127 (3)0.6475 (2)0.61354 (13)0.0387 (5)
N7A0.5741 (3)0.8363 (2)0.47828 (12)0.0372 (5)
N9A0.6624 (4)0.6405 (2)0.47547 (13)0.0393 (5)
H9A0.698 (5)0.564 (2)0.460 (2)0.072 (12)*
N10A0.5634 (3)1.0203 (2)0.63604 (13)0.0380 (5)
H10A0.593 (4)1.071 (3)0.6826 (13)0.050 (9)*
H10B0.530 (4)1.046 (3)0.5930 (14)0.046 (9)*
C2B0.7945 (4)0.3311 (3)0.36801 (17)0.0442 (7)
H2B0.76190.37180.32810.053*
C4B0.8345 (4)0.3324 (2)0.49323 (15)0.0338 (5)
C5B0.8874 (4)0.2095 (2)0.47870 (15)0.0321 (5)
C6B0.8929 (4)0.1471 (2)0.40071 (15)0.0333 (5)
C8B0.9002 (5)0.2713 (3)0.60105 (17)0.0497 (8)
H8B0.91710.27340.65420.060*
N1B0.8443 (4)0.2124 (2)0.34539 (13)0.0410 (5)
H1B0.84550.17800.29670.049*0.50
N3B0.7854 (3)0.3980 (2)0.43926 (14)0.0405 (5)
N7B0.9286 (4)0.1717 (2)0.54750 (13)0.0430 (6)
N9B0.8439 (4)0.3711 (2)0.57239 (14)0.0434 (6)
H9B0.821 (5)0.445 (2)0.5964 (19)0.060 (10)*
N10B0.9440 (4)0.0304 (2)0.37866 (14)0.0438 (6)
H10C0.951 (5)0.002 (3)0.3298 (12)0.056 (10)*
H10D0.970 (4)0.017 (3)0.4126 (16)0.047 (9)*
C120.7985 (3)1.4372 (2)1.03938 (14)0.0288 (5)
H120.84561.40281.08020.035*
C140.7287 (4)1.5725 (2)0.96816 (16)0.0362 (6)
H140.72001.64820.95160.043*
C150.6590 (3)1.4561 (2)0.92890 (15)0.0325 (5)
H150.59261.43640.88020.039*
C160.6578 (3)1.2343 (2)0.95667 (14)0.0265 (5)
H16A0.54681.21500.92100.032*
H16B0.63111.20841.00440.032*
C170.8131 (3)1.15684 (19)0.92018 (12)0.0200 (4)
N110.7048 (3)1.37228 (18)0.97454 (11)0.0255 (4)
N130.8145 (3)1.5578 (2)1.03686 (13)0.0328 (5)
H130.875 (4)1.618 (2)1.0727 (15)0.048 (9)*
O180.9822 (2)1.19553 (16)0.96786 (9)0.0282 (4)
H180.997 (5)1.150 (3)0.9998 (16)0.051 (10)*
O190.9798 (2)1.30606 (16)0.83553 (10)0.0328 (4)
O200.6725 (2)1.18517 (17)0.77726 (10)0.0335 (4)
O210.9583 (2)1.06948 (17)0.78296 (10)0.0324 (4)
H211.064 (3)1.068 (3)0.8052 (19)0.059 (11)*
O220.6647 (2)0.97883 (16)0.99016 (9)0.0290 (4)
H220.55620.99570.98740.044*0.50
O230.9260 (2)0.91896 (16)0.91238 (10)0.0303 (4)
O240.6112 (2)0.93812 (15)0.84278 (9)0.0281 (4)
P10.85349 (8)1.18687 (5)0.82327 (3)0.02295 (15)
P20.74712 (8)0.98543 (5)0.91318 (3)0.02200 (14)
O1W1.2782 (4)1.0626 (4)0.85746 (18)0.0425 (10)0.899 (14)
O1W'1.250 (4)1.002 (4)0.8420 (17)0.055 (5)0.101 (14)
H1W1.248 (5)1.033 (3)0.8952 (15)0.066*
H2W1.362 (4)1.016 (3)0.8321 (18)0.066*
O2W0.4121 (4)0.7124 (2)0.84922 (15)0.0657 (7)
H3W0.483 (5)0.780 (2)0.846 (2)0.079*
H4W0.447 (5)0.647 (2)0.814 (2)0.079*
O3W0.3260 (4)0.2868 (3)0.76294 (19)0.0728 (8)
H5W0.403 (4)0.233 (3)0.775 (2)0.087*
H6W0.232 (4)0.284 (4)0.790 (2)0.087*
O4W0.8724 (4)0.4914 (2)0.75162 (15)0.0670 (7)
H7W0.905 (5)0.428 (2)0.773 (2)0.080*
H8W0.938 (5)0.561 (2)0.775 (2)0.080*
O5W0.4851 (5)0.5039 (3)0.7396 (2)0.0803 (8)
H9W0.422 (5)0.435 (3)0.747 (3)0.096*
H10W0.604 (3)0.487 (4)0.741 (3)0.096*
O6W0.057 (2)0.7648 (14)0.7999 (7)0.057 (2)0.50
H12W0.020 (8)0.829 (5)0.832 (3)0.068*0.50
O6W'0.052 (2)0.7297 (13)0.8142 (8)0.085 (4)0.50
H12'0.011 (8)0.783 (8)0.845 (5)0.102*0.50
H11W0.159 (4)0.741 (5)0.818 (2)0.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C2A0.0464 (16)0.0419 (15)0.0311 (13)0.0071 (12)0.0005 (11)0.0140 (11)
C4A0.0362 (13)0.0278 (12)0.0310 (13)0.0064 (10)0.0018 (10)0.0046 (10)
C5A0.0363 (13)0.0273 (12)0.0247 (12)0.0055 (10)0.0009 (9)0.0038 (9)
C6A0.0307 (12)0.0303 (12)0.0259 (12)0.0029 (10)0.0006 (9)0.0038 (9)
C8A0.0645 (19)0.0361 (14)0.0264 (13)0.0137 (13)0.0009 (12)0.0027 (11)
N1A0.0434 (12)0.0348 (12)0.0213 (10)0.0041 (9)0.0007 (9)0.0023 (9)
N3A0.0516 (14)0.0324 (12)0.0332 (12)0.0110 (10)0.0015 (10)0.0080 (9)
N7A0.0559 (14)0.0319 (11)0.0242 (10)0.0119 (10)0.0002 (9)0.0056 (8)
N9A0.0583 (15)0.0275 (11)0.0309 (11)0.0143 (10)0.0043 (10)0.0010 (9)
N10A0.0560 (15)0.0284 (11)0.0269 (11)0.0110 (10)0.0019 (10)0.0000 (9)
C2B0.0592 (18)0.0402 (15)0.0378 (15)0.0191 (13)0.0066 (13)0.0140 (12)
C4B0.0370 (13)0.0286 (12)0.0358 (14)0.0065 (10)0.0080 (11)0.0047 (10)
C5B0.0378 (13)0.0292 (12)0.0306 (13)0.0071 (10)0.0065 (10)0.0075 (10)
C6B0.0376 (14)0.0333 (13)0.0301 (13)0.0096 (10)0.0075 (10)0.0063 (10)
C8B0.075 (2)0.0427 (17)0.0323 (15)0.0149 (15)0.0055 (14)0.0074 (12)
N1B0.0603 (15)0.0384 (13)0.0270 (11)0.0173 (11)0.0085 (10)0.0082 (9)
N3B0.0544 (14)0.0313 (12)0.0389 (13)0.0142 (10)0.0094 (11)0.0101 (9)
N7B0.0616 (16)0.0379 (13)0.0310 (12)0.0149 (11)0.0048 (11)0.0079 (10)
N9B0.0629 (16)0.0300 (12)0.0363 (13)0.0125 (11)0.0096 (11)0.0006 (10)
N10B0.0703 (17)0.0362 (13)0.0254 (12)0.0213 (12)0.0059 (11)0.0031 (10)
C120.0287 (12)0.0276 (12)0.0272 (12)0.0020 (9)0.0032 (9)0.0006 (9)
C140.0366 (14)0.0268 (13)0.0460 (15)0.0058 (10)0.0071 (11)0.0074 (11)
C150.0344 (13)0.0329 (13)0.0299 (12)0.0070 (10)0.0013 (10)0.0055 (10)
C160.0285 (11)0.0210 (11)0.0273 (11)0.0001 (9)0.0078 (9)0.0019 (9)
C170.0216 (10)0.0185 (10)0.0186 (10)0.0009 (8)0.0016 (8)0.0017 (8)
N110.0264 (10)0.0224 (9)0.0257 (10)0.0032 (7)0.0059 (7)0.0005 (7)
N130.0310 (11)0.0255 (10)0.0367 (12)0.0005 (8)0.0039 (9)0.0044 (9)
O180.0292 (9)0.0292 (9)0.0248 (8)0.0039 (7)0.0062 (6)0.0073 (7)
O190.0413 (10)0.0302 (9)0.0265 (9)0.0057 (7)0.0035 (7)0.0075 (7)
O200.0354 (9)0.0384 (10)0.0252 (8)0.0057 (7)0.0032 (7)0.0050 (7)
O210.0348 (10)0.0362 (10)0.0236 (8)0.0080 (8)0.0056 (7)0.0015 (7)
O220.0292 (9)0.0341 (9)0.0255 (8)0.0019 (7)0.0050 (7)0.0094 (7)
O230.0313 (9)0.0308 (9)0.0296 (9)0.0092 (7)0.0026 (7)0.0069 (7)
O240.0298 (8)0.0281 (8)0.0240 (8)0.0018 (7)0.0014 (6)0.0030 (6)
P10.0266 (3)0.0244 (3)0.0169 (3)0.0017 (2)0.0020 (2)0.0024 (2)
P20.0247 (3)0.0200 (3)0.0204 (3)0.0012 (2)0.0009 (2)0.0031 (2)
O1W0.0349 (13)0.056 (2)0.0402 (15)0.0108 (14)0.0067 (10)0.0157 (15)
O1W'0.035 (8)0.070 (10)0.072 (9)0.007 (8)0.008 (8)0.037 (8)
O2W0.0815 (18)0.0505 (14)0.0636 (16)0.0160 (13)0.0101 (13)0.0133 (12)
O3W0.0583 (16)0.0790 (19)0.097 (2)0.0192 (14)0.0278 (15)0.0445 (16)
O4W0.096 (2)0.0481 (14)0.0605 (16)0.0103 (14)0.0016 (14)0.0212 (12)
O5W0.087 (2)0.0682 (19)0.090 (2)0.0054 (16)0.0149 (18)0.0247 (16)
O6W0.055 (3)0.079 (6)0.038 (3)0.020 (4)0.014 (2)0.011 (3)
O6W'0.062 (4)0.095 (8)0.071 (7)0.026 (5)0.010 (5)0.042 (5)
Geometric parameters (Å, º) top
C2A—N3A1.303 (4)C14—H140.9300
C2A—N1A1.347 (3)C15—N111.372 (3)
C2A—H2A0.9300C15—H150.9300
C4A—N9A1.347 (3)C16—N111.470 (3)
C4A—N3A1.355 (3)C16—C171.540 (3)
C4A—C5A1.383 (3)C16—H16A0.9700
C5A—N7A1.370 (3)C16—H16B0.9700
C5A—C6A1.403 (3)C17—O181.426 (3)
C6A—N10A1.304 (3)C17—P11.846 (2)
C6A—N1A1.367 (3)C17—P21.861 (2)
C8A—N7A1.311 (3)N13—H130.876 (18)
C8A—N9A1.352 (3)O18—H180.828 (18)
C8A—H8A0.9300O19—P11.5053 (17)
N1A—H1A0.857 (18)O20—P11.4911 (17)
N9A—H9A0.877 (19)O21—P11.5797 (17)
N10A—H10A0.888 (18)O21—H210.839 (18)
N10A—H10B0.886 (18)O22—P21.5367 (16)
C2B—N3B1.316 (4)O22—H220.8200
C2B—N1B1.337 (3)O23—P21.5202 (17)
C2B—H2B0.9300O24—P21.5054 (16)
C4B—N3B1.342 (3)O1W—H1W0.835 (18)
C4B—N9B1.363 (3)O1W—H2W0.897 (17)
C4B—C5B1.378 (3)O1W'—H1W0.93 (2)
C5B—N7B1.378 (3)O1W'—H2W0.860 (19)
C5B—C6B1.399 (3)O2W—H3W0.888 (18)
C6B—N10B1.320 (3)O2W—H4W0.893 (18)
C6B—N1B1.358 (3)O3W—H5W0.873 (18)
C8B—N7B1.307 (4)O3W—H6W0.867 (18)
C8B—N9B1.355 (4)O4W—H7W0.882 (18)
C8B—H8B0.9300O4W—H8W0.870 (18)
N1B—H1B0.8600O5W—H9W0.888 (19)
N9B—H9B0.856 (18)O5W—H10W0.895 (19)
N10B—H10C0.862 (18)O6W—H12W0.87 (2)
N10B—H10D0.887 (18)O6W—H12'0.96 (6)
C12—N131.312 (3)O6W—H11W0.860 (19)
C12—N111.322 (3)O6W'—H12W1.10 (4)
C12—H120.9300O6W'—H12'0.88 (2)
C14—C151.348 (4)O6W'—H11W0.78 (4)
C14—N131.364 (4)
N3A—C2A—N1A125.9 (2)N13—C12—N11109.1 (2)
N3A—C2A—H2A117.0N13—C12—H12125.5
N1A—C2A—H2A117.0N11—C12—H12125.5
N9A—C4A—N3A126.9 (2)C15—C14—N13106.9 (2)
N9A—C4A—C5A105.7 (2)C15—C14—H14126.5
N3A—C4A—C5A127.3 (2)N13—C14—H14126.5
N7A—C5A—C4A110.9 (2)C14—C15—N11107.0 (2)
N7A—C5A—C6A130.9 (2)C14—C15—H15126.5
C4A—C5A—C6A118.1 (2)N11—C15—H15126.5
N10A—C6A—N1A121.1 (2)N11—C16—C17113.13 (18)
N10A—C6A—C5A125.6 (2)N11—C16—H16A109.0
N1A—C6A—C5A113.3 (2)C17—C16—H16A109.0
N7A—C8A—N9A114.2 (2)N11—C16—H16B109.0
N7A—C8A—H8A122.9C17—C16—H16B109.0
N9A—C8A—H8A122.9H16A—C16—H16B107.8
C2A—N1A—C6A123.7 (2)O18—C17—C16109.35 (17)
C2A—N1A—H1A116 (2)O18—C17—P1106.21 (14)
C6A—N1A—H1A120 (2)C16—C17—P1111.62 (15)
C2A—N3A—C4A111.6 (2)O18—C17—P2110.80 (14)
C8A—N7A—C5A103.0 (2)C16—C17—P2108.11 (14)
C4A—N9A—C8A106.2 (2)P1—C17—P2110.77 (11)
C4A—N9A—H9A123 (3)C12—N11—C15108.1 (2)
C8A—N9A—H9A131 (3)C12—N11—C16124.8 (2)
C6A—N10A—H10A119 (2)C15—N11—C16127.1 (2)
C6A—N10A—H10B115 (2)C12—N13—C14108.9 (2)
H10A—N10A—H10B125 (3)C12—N13—H13125 (2)
N3B—C2B—N1B128.6 (3)C14—N13—H13126 (2)
N3B—C2B—H2B115.7C17—O18—H18111 (2)
N1B—C2B—H2B115.7P1—O21—H21112 (2)
N3B—C4B—N9B128.3 (2)P2—O22—H22109.5
N3B—C4B—C5B126.0 (2)O20—P1—O19116.79 (10)
N9B—C4B—C5B105.7 (2)O20—P1—O21108.41 (10)
N7B—C5B—C4B110.7 (2)O19—P1—O21109.24 (10)
N7B—C5B—C6B131.8 (2)O20—P1—C17109.44 (10)
C4B—C5B—C6B117.5 (2)O19—P1—C17107.78 (9)
N10B—C6B—N1B119.0 (2)O21—P1—C17104.50 (10)
N10B—C6B—C5B123.8 (2)O24—P2—O23115.30 (10)
N1B—C6B—C5B117.2 (2)O24—P2—O22112.91 (10)
N7B—C8B—N9B114.1 (3)O23—P2—O22107.18 (9)
N7B—C8B—H8B123.0O24—P2—C17108.67 (9)
N9B—C8B—H8B123.0O23—P2—C17106.62 (10)
C2B—N1B—C6B118.8 (2)O22—P2—C17105.55 (10)
C2B—N1B—H1B120.6H1W—O1W—H2W110 (3)
C6B—N1B—H1B120.6H1W—O1W'—H2W105 (3)
C2B—N3B—C4B111.8 (2)H3W—O2W—H4W107 (2)
C8B—N7B—C5B103.5 (2)H5W—O3W—H6W108 (3)
C8B—N9B—C4B106.0 (2)H7W—O4W—H8W109 (3)
C8B—N9B—H9B130 (2)H9W—O5W—H10W107 (3)
C4B—N9B—H9B124 (2)H12W—O6W—H11W111 (3)
C6B—N10B—H10C120 (2)H12'—O6W—H11W103 (5)
C6B—N10B—H10D122 (2)H12W—O6W'—H11W98 (4)
H10C—N10B—H10D118 (3)H12'—O6W'—H11W119 (5)
N9A—C4A—C5A—N7A0.5 (3)C4B—C5B—N7B—C8B0.1 (3)
N3A—C4A—C5A—N7A178.7 (3)C6B—C5B—N7B—C8B178.9 (3)
N9A—C4A—C5A—C6A177.1 (2)N7B—C8B—N9B—C4B0.2 (4)
N3A—C4A—C5A—C6A2.1 (4)N3B—C4B—N9B—C8B180.0 (3)
N7A—C5A—C6A—N10A1.5 (5)C5B—C4B—N9B—C8B0.2 (3)
C4A—C5A—C6A—N10A177.3 (3)N13—C14—C15—N110.3 (3)
N7A—C5A—C6A—N1A178.3 (3)N11—C16—C17—O1851.9 (2)
C4A—C5A—C6A—N1A2.5 (3)N11—C16—C17—P165.3 (2)
N3A—C2A—N1A—C6A0.2 (5)N11—C16—C17—P2172.60 (15)
N10A—C6A—N1A—C2A178.2 (3)N13—C12—N11—C150.1 (3)
C5A—C6A—N1A—C2A1.5 (4)N13—C12—N11—C16179.3 (2)
N1A—C2A—N3A—C4A0.8 (4)C14—C15—N11—C120.3 (3)
N9A—C4A—N3A—C2A178.7 (3)C14—C15—N11—C16179.5 (2)
C5A—C4A—N3A—C2A0.4 (4)C17—C16—N11—C1285.1 (3)
N9A—C8A—N7A—C5A0.2 (3)C17—C16—N11—C1595.8 (3)
C4A—C5A—N7A—C8A0.2 (3)N11—C12—N13—C140.1 (3)
C6A—C5A—N7A—C8A176.3 (3)C15—C14—N13—C120.3 (3)
N3A—C4A—N9A—C8A178.7 (3)O18—C17—P1—O20163.63 (13)
C5A—C4A—N9A—C8A0.6 (3)C16—C17—P1—O2044.54 (17)
N7A—C8A—N9A—C4A0.5 (4)P2—C17—P1—O2075.99 (13)
N3B—C4B—C5B—N7B180.0 (3)O18—C17—P1—O1935.68 (16)
N9B—C4B—C5B—N7B0.2 (3)C16—C17—P1—O1983.42 (17)
N3B—C4B—C5B—C6B0.8 (4)P2—C17—P1—O19156.06 (11)
N9B—C4B—C5B—C6B178.9 (2)O18—C17—P1—O2180.44 (15)
N7B—C5B—C6B—N10B0.1 (5)C16—C17—P1—O21160.46 (15)
C4B—C5B—C6B—N10B178.8 (3)P2—C17—P1—O2139.93 (13)
N7B—C5B—C6B—N1B179.4 (3)O18—C17—P2—O24160.46 (14)
C4B—C5B—C6B—N1B0.5 (4)C16—C17—P2—O2479.73 (16)
N3B—C2B—N1B—C6B0.3 (5)P1—C17—P2—O2442.86 (14)
N10B—C6B—N1B—C2B179.3 (3)O18—C17—P2—O2335.60 (16)
C5B—C6B—N1B—C2B0.0 (4)C16—C17—P2—O23155.41 (14)
N1B—C2B—N3B—C4B0.0 (5)P1—C17—P2—O2382.00 (12)
N9B—C4B—N3B—C2B179.1 (3)O18—C17—P2—O2278.16 (16)
C5B—C4B—N3B—C2B0.5 (4)C16—C17—P2—O2241.64 (16)
N9B—C8B—N7B—C5B0.1 (4)P1—C17—P2—O22164.24 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O240.86 (2)1.93 (2)2.755 (3)161 (3)
N9A—H9A···N3B0.88 (2)1.90 (2)2.775 (3)173 (4)
N10A—H10A···O200.89 (2)1.88 (2)2.764 (3)175 (3)
N10A—H10B···N7Ai0.89 (2)2.10 (2)2.944 (3)159 (3)
N1B—H1B···O6Wii0.862.092.765 (10)135
N9B—H9B···N3A0.86 (2)2.33 (2)3.138 (3)158 (3)
N10B—H10C···O21iii0.86 (2)2.13 (2)2.974 (3)166 (3)
N10B—H10D···N7Biv0.89 (2)2.09 (2)2.929 (3)157 (3)
N13—H13···O19v0.88 (2)1.87 (2)2.700 (3)158 (3)
O18—H18···O23vi0.83 (2)1.92 (2)2.726 (2)165 (3)
O21—H21···O1W0.84 (2)1.76 (2)2.599 (4)176 (4)
O21—H21···O1W0.84 (2)1.72 (4)2.51 (3)157 (4)
O22—H22···O22vii0.821.712.500 (3)162
O1W—H1W···O22vi0.83 (3)2.12 (3)2.820 (4)143 (3)
O1W—H2W···O24viii0.90 (3)2.03 (3)2.837 (4)148 (3)
O2W—H3W···O240.89 (2)1.91 (2)2.792 (3)173 (4)
O2W—H4W···O5W0.89 (2)1.85 (2)2.739 (4)172 (4)
O3W—H5W···O20ix0.87 (2)2.06 (2)2.821 (3)146 (4)
O3W—H6W···O19x0.87 (2)2.06 (2)2.906 (3)165 (4)
O4W—H7W···O19ix0.88 (2)1.97 (2)2.841 (3)171 (4)
O4W—H8W···O6Wviii0.87 (2)2.26 (2)3.091 (15)159 (3)
O5W—H9W···O3W0.89 (2)1.80 (2)2.680 (4)172 (4)
O5W—H10W···O4W0.90 (2)1.94 (2)2.823 (5)167 (4)
O6W—H11W···O2W0.85 (3)1.93 (3)2.791 (15)169 (4)
O6W—H12W···O23xi0.87 (2)1.74 (4)2.580 (15)161 (8)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+1, z+1; (iii) x+2, y+1, z+1; (iv) x+2, y, z+1; (v) x+2, y+3, z+2; (vi) x+2, y+2, z+2; (vii) x+1, y+2, z+2; (viii) x+1, y, z; (ix) x, y1, z; (x) x1, y1, z; (xi) x1, y, z.
Selected geometric parameters (Å ,°) for (I) and (II) top
Parameter(I)(II)
P1—O191.5033 (18)1.5050 (17)
P1—O201.4931 (19)1.4908 (17)
P1—O211.5792 (19)*1.5797 (17)*
P2—O221.5101 (18)1.5361 (16)*
P2—O231.5282 (18)1.5205 (17)
P2—O241.5167 (17)1.5050 (16)
C2—N11.346 (4)/1.349 (4)#1.346 (3)/1.337 (3)#
N1—C61.388 (4)/1.370 (3)#1.366 (3)/1.357 (3)#
O19—P1—O20116.14 (12)116.81 (10)
O20—P1—O21108.74 (11)$108.43 (10)$
O21—P1—O19109.12 (11)$109.25 (10)$
O22—P2—O23111.64 (10)107.17 (19)$
O23—P2—O24113.63 (10)115.31 (10)
O24—P2—O22111.88 (11)112.93 (10)$
C2—N1—C6123.6 (2)/123.5 (2)#123.7 (2)/118.9 (2)#
C17—C16—N11—C12-85.5 (3)-85.2 (3)
N11—C16—C17—P1-65.2 (2)-65.3 (2)
N11—C16—C17—P2171.07 (17)172.64 (15)
Notes: (*) P—OH distance; ($) O—P—OH angle; (#) data for cations A and B, respectively.
 

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