Tetra- and hexa­hydrates of bis­(aden­inium) zoledronate

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⁺·C₅H₈N₂O₇P₂^2-·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⁺·C₅H₈N₂O₇P₂^2-·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).

Computing details

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

Crystal data

2C5H6N5^+·C5H8N2O7P2^2^−·4H2O	F(000) = 1280
Mr = 614.43	Dx = 1.648 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5448 reflections
a = 7.2128 (7) Å	θ = 2.4–27.7°
b = 17.7448 (17) Å	µ = 0.26 mm^−1
c = 19.3945 (18) Å	T = 294 K
β = 93.999 (2)°	Block, colorless
V = 2476.3 (4) Å^3	0.19 × 0.16 × 0.07 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5901 independent reflections
Radiation source: fine-focus sealed tube	5410 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω scan	θmax = 28.0°, θmin = 1.6°
Absorption correction: multi-scan (SABABS; Bruker, 2001)	h = −9→9
Tmin = 0.93, Tmax = 0.98	k = −23→23
28416 measured reflections	l = −25→25

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0531P)^2 + 2.9198P] where P = (Fo^2 + 2Fc^2)/3
5901 reflections	(Δ/σ)max = 0.001
439 parameters	Δρmax = 0.75 e Å^−3
23 restraints	Δρmin = −0.42 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C2A	0.5260 (4)	0.25330 (18)	−0.07844 (15)	0.0435 (7)
H2A	0.4994	0.2115	−0.1063	0.052*
C4A	0.5302 (3)	0.31295 (16)	0.02134 (14)	0.0341 (6)
C5A	0.6097 (3)	0.37845 (16)	−0.00415 (13)	0.0331 (5)
C6A	0.6491 (3)	0.37961 (15)	−0.07343 (14)	0.0332 (5)
C8A	0.5755 (4)	0.39843 (17)	0.10047 (15)	0.0403 (6)
H8A	0.5755	0.4215	0.1435	0.048*
N1A	0.6051 (3)	0.31278 (15)	−0.10796 (12)	0.0387 (5)
H1A	0.636 (5)	0.306 (2)	−0.1516 (11)	0.065 (11)*
N3A	0.4832 (3)	0.24907 (15)	−0.01402 (12)	0.0415 (6)
N7A	0.6384 (3)	0.43184 (13)	0.04610 (12)	0.0360 (5)
N9A	0.5109 (3)	0.32759 (14)	0.08845 (12)	0.0358 (5)
H9A	0.465 (5)	0.2984 (19)	0.1210 (16)	0.064 (11)*
N10A	0.7236 (3)	0.43561 (13)	−0.10584 (12)	0.0342 (5)
H10A	0.758 (4)	0.4769 (13)	−0.0847 (15)	0.041 (9)*
H10B	0.742 (5)	0.432 (2)	−0.1500 (10)	0.056 (10)*
C2B	0.9969 (4)	0.76027 (17)	0.06231 (14)	0.0400 (6)
H2B	1.0256	0.8020	0.0900	0.048*
C4B	0.9816 (3)	0.70141 (14)	−0.03749 (13)	0.0301 (5)
C5B	0.9081 (3)	0.63592 (14)	−0.01097 (13)	0.0299 (5)
C6B	0.8790 (3)	0.63405 (15)	0.05976 (13)	0.0301 (5)
C8B	0.9384 (4)	0.61454 (16)	−0.11626 (14)	0.0356 (6)
H8B	0.9361	0.5912	−0.1593	0.043*
N1B	0.9297 (3)	0.69932 (14)	0.09376 (11)	0.0354 (5)
H1B	0.925 (4)	0.7015 (18)	0.1399 (9)	0.041 (8)*
N3B	1.0256 (3)	0.76644 (13)	−0.00340 (12)	0.0384 (5)
N7B	0.8811 (3)	0.58140 (12)	−0.06098 (11)	0.0329 (5)
N9B	1.0012 (3)	0.68584 (13)	−0.10488 (11)	0.0338 (5)
H9B	1.037 (5)	0.7174 (17)	−0.1361 (15)	0.055 (10)*
N10B	0.8096 (3)	0.57685 (14)	0.09271 (12)	0.0365 (5)
H10C	0.811 (5)	0.577 (2)	0.1384 (10)	0.050 (9)*
H10D	0.775 (4)	0.5369 (13)	0.0702 (14)	0.037 (8)*
C12	1.1858 (4)	0.57213 (16)	0.49525 (12)	0.0330 (5)
H12	1.1432	0.6196	0.5070	0.040*
C14	1.2700 (4)	0.45392 (17)	0.50172 (14)	0.0391 (6)
H14	1.2947	0.4058	0.5191	0.047*
C15	1.2933 (4)	0.47780 (15)	0.43687 (14)	0.0345 (6)
H15	1.3376	0.4495	0.4012	0.041*
C16	1.2436 (3)	0.60388 (14)	0.37435 (12)	0.0286 (5)
H16A	1.3376	0.5863	0.3448	0.034*
H16B	1.2817	0.6532	0.3915	0.034*
C17	1.0595 (3)	0.61235 (12)	0.33032 (11)	0.0223 (4)
O18	0.9207 (2)	0.63287 (11)	0.37640 (9)	0.0309 (4)
H18	0.820 (4)	0.649 (2)	0.3548 (19)	0.071 (13)*
O19	0.9351 (3)	0.46788 (10)	0.33925 (9)	0.0382 (4)
O20	1.1339 (3)	0.50032 (11)	0.24013 (11)	0.0407 (5)
O21	0.8067 (3)	0.54653 (11)	0.23936 (9)	0.0349 (4)
H21	0.707 (4)	0.528 (2)	0.254 (2)	0.073 (13)*
O22	1.1557 (3)	0.75892 (10)	0.31491 (9)	0.0332 (4)
O23	0.9200 (2)	0.70529 (10)	0.22666 (9)	0.0310 (4)
O24	1.2601 (2)	0.66607 (10)	0.22820 (9)	0.0329 (4)
N11	1.2389 (3)	0.55209 (12)	0.43374 (10)	0.0287 (4)
N13	1.2035 (3)	0.51335 (14)	0.53708 (11)	0.0370 (5)
H13	1.168 (6)	0.514 (2)	0.5801 (12)	0.075 (13)*
P1	0.98661 (8)	0.52422 (3)	0.28594 (3)	0.02453 (15)
P2	1.10190 (8)	0.69171 (3)	0.27012 (3)	0.02273 (14)
O1W	1.1037 (3)	0.79444 (14)	−0.20060 (11)	0.0476 (5)
H1W	1.180 (4)	0.789 (2)	−0.2318 (15)	0.057*
H2W	1.003 (4)	0.806 (2)	−0.2242 (17)	0.057*
O2W	0.5014 (3)	0.48671 (16)	0.2722 (2)	0.0762 (9)
H3W	0.529 (7)	0.4410 (14)	0.282 (2)	0.091*
H4W	0.387 (3)	0.495 (3)	0.261 (2)	0.091*
O3W	1.1906 (6)	0.33913 (17)	0.30286 (18)	0.0978 (12)
H5W	1.227 (8)	0.323 (3)	0.2646 (17)	0.117*
H6W	1.147 (8)	0.3829 (17)	0.295 (3)	0.117*
O4W	0.6643 (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)
H7W	0.758 (7)	0.374 (3)	0.317 (3)	0.087*
H8W	0.664 (7)	0.321 (3)	0.289 (3)	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2A	0.0408 (15)	0.0500 (17)	0.0397 (15)	−0.0031 (13)	0.0025 (12)	−0.0041 (13)
C4A	0.0237 (11)	0.0427 (15)	0.0358 (13)	0.0012 (10)	0.0024 (10)	0.0119 (11)
C5A	0.0288 (12)	0.0400 (14)	0.0305 (12)	0.0028 (10)	0.0023 (10)	0.0037 (10)
C6A	0.0253 (12)	0.0376 (13)	0.0369 (13)	0.0048 (10)	0.0033 (10)	0.0071 (11)
C8A	0.0431 (15)	0.0439 (16)	0.0345 (14)	0.0022 (12)	0.0064 (11)	0.0039 (12)
N1A	0.0345 (12)	0.0557 (15)	0.0265 (11)	0.0001 (10)	0.0067 (9)	−0.0022 (10)
N3A	0.0355 (12)	0.0562 (15)	0.0336 (12)	−0.0024 (11)	0.0078 (9)	0.0063 (11)
N7A	0.0368 (12)	0.0340 (12)	0.0373 (12)	0.0013 (9)	0.0028 (9)	0.0014 (9)
N9A	0.0340 (11)	0.0407 (13)	0.0334 (12)	0.0009 (10)	0.0064 (9)	0.0094 (10)
N10A	0.0396 (12)	0.0346 (12)	0.0292 (11)	−0.0018 (10)	0.0099 (9)	0.0063 (9)
C2B	0.0418 (15)	0.0415 (15)	0.0357 (14)	0.0014 (12)	−0.0051 (11)	−0.0082 (12)
C4B	0.0264 (11)	0.0341 (13)	0.0292 (12)	0.0040 (10)	−0.0016 (9)	0.0053 (10)
C5B	0.0282 (12)	0.0327 (12)	0.0284 (12)	0.0037 (10)	−0.0018 (9)	0.0004 (10)
C6B	0.0252 (11)	0.0361 (13)	0.0287 (12)	0.0045 (10)	−0.0014 (9)	0.0011 (10)
C8B	0.0388 (14)	0.0390 (14)	0.0290 (12)	0.0031 (11)	0.0011 (10)	−0.0010 (11)
N1B	0.0374 (12)	0.0454 (13)	0.0228 (10)	0.0035 (10)	−0.0018 (9)	−0.0045 (9)
N3B	0.0410 (13)	0.0395 (12)	0.0342 (12)	−0.0002 (10)	−0.0001 (10)	0.0005 (10)
N7B	0.0352 (11)	0.0328 (11)	0.0302 (11)	−0.0001 (9)	−0.0001 (9)	−0.0027 (9)
N9B	0.0354 (11)	0.0374 (12)	0.0286 (11)	0.0022 (9)	0.0014 (9)	0.0052 (9)
N10B	0.0403 (12)	0.0423 (13)	0.0269 (11)	−0.0032 (10)	0.0029 (9)	0.0046 (10)
C12	0.0335 (13)	0.0397 (14)	0.0253 (12)	−0.0049 (11)	−0.0003 (10)	0.0016 (10)
C14	0.0374 (14)	0.0407 (15)	0.0382 (14)	−0.0021 (11)	−0.0032 (11)	0.0124 (12)
C15	0.0355 (13)	0.0341 (13)	0.0335 (13)	0.0016 (11)	0.0003 (10)	0.0028 (10)
C16	0.0304 (12)	0.0313 (12)	0.0237 (11)	−0.0072 (10)	−0.0008 (9)	0.0047 (9)
C17	0.0263 (11)	0.0209 (10)	0.0201 (10)	−0.0024 (8)	0.0046 (8)	−0.0009 (8)
O18	0.0311 (9)	0.0406 (10)	0.0220 (8)	0.0018 (8)	0.0095 (7)	0.0000 (7)
O19	0.0523 (12)	0.0298 (9)	0.0314 (9)	−0.0109 (8)	−0.0042 (8)	0.0068 (7)
O20	0.0370 (10)	0.0371 (10)	0.0488 (12)	−0.0016 (8)	0.0093 (9)	−0.0164 (9)
O21	0.0308 (9)	0.0418 (10)	0.0312 (9)	−0.0108 (8)	−0.0045 (7)	0.0089 (8)
O22	0.0409 (10)	0.0267 (9)	0.0327 (9)	−0.0048 (7)	0.0059 (8)	−0.0045 (7)
O23	0.0330 (9)	0.0325 (9)	0.0274 (8)	0.0013 (7)	0.0010 (7)	0.0034 (7)
O24	0.0354 (9)	0.0332 (9)	0.0317 (9)	0.0021 (7)	0.0144 (7)	0.0028 (7)
N11	0.0291 (10)	0.0337 (11)	0.0229 (9)	−0.0045 (8)	−0.0011 (8)	0.0026 (8)
N13	0.0375 (12)	0.0491 (14)	0.0243 (11)	−0.0065 (10)	0.0005 (9)	0.0072 (10)
P1	0.0271 (3)	0.0237 (3)	0.0227 (3)	−0.0033 (2)	0.0010 (2)	−0.0007 (2)
P2	0.0269 (3)	0.0216 (3)	0.0202 (3)	−0.0008 (2)	0.0052 (2)	0.0001 (2)
O1W	0.0341 (11)	0.0693 (15)	0.0399 (11)	−0.0011 (10)	0.0069 (9)	0.0120 (10)
O2W	0.0323 (12)	0.0626 (17)	0.135 (3)	−0.0018 (12)	0.0169 (15)	0.0283 (18)
O3W	0.170 (4)	0.0441 (15)	0.086 (2)	0.0370 (19)	0.059 (2)	0.0103 (15)
O4W	0.068 (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)

C2A—N3A	1.310 (4)	C12—N13	1.322 (3)
C2A—N1A	1.346 (4)	C12—N11	1.327 (3)
C2A—H2A	0.9300	C12—H12	0.9300
C4A—N9A	1.344 (4)	C14—C15	1.349 (4)
C4A—N3A	1.356 (4)	C14—N13	1.363 (4)
C4A—C5A	1.401 (4)	C14—H14	0.9300
C5A—N7A	1.365 (3)	C15—N11	1.376 (3)
C5A—C6A	1.393 (4)	C15—H15	0.9300
C6A—N10A	1.311 (3)	C16—N11	1.476 (3)
C6A—N1A	1.388 (4)	C16—C17	1.535 (3)
C8A—N7A	1.318 (4)	C16—H16A	0.9700
C8A—N9A	1.355 (4)	C16—H16B	0.9700
C8A—H8A	0.9300	C17—O18	1.435 (3)
N1A—H1A	0.898 (18)	C17—P1	1.844 (2)
N9A—H9A	0.896 (18)	C17—P2	1.868 (2)
N10A—H10A	0.867 (18)	O18—H18	0.857 (19)
N10A—H10B	0.879 (18)	O19—P1	1.5033 (18)
C2B—N3B	1.310 (4)	O20—P1	1.4931 (19)
C2B—N1B	1.349 (4)	O21—P1	1.5792 (19)
C2B—H2B	0.9300	O21—H21	0.859 (19)
C4B—N9B	1.353 (3)	O22—P2	1.5101 (18)
C4B—N3B	1.356 (3)	O23—P2	1.5282 (18)
C4B—C5B	1.391 (4)	O24—P2	1.5167 (17)
C5B—N7B	1.374 (3)	N13—H13	0.889 (19)
C5B—C6B	1.402 (3)	O1W—H1W	0.852 (18)
C6B—N10B	1.317 (3)	O1W—H2W	0.861 (18)
C6B—N1B	1.370 (3)	O2W—H3W	0.852 (19)
C8B—N7B	1.314 (3)	O2W—H4W	0.853 (19)
C8B—N9B	1.357 (4)	O3W—H5W	0.85 (2)
C8B—H8B	0.9300	O3W—H6W	0.85 (2)
N1B—H1B	0.899 (18)	O4W—H7W	0.75 (5)
N9B—H9B	0.877 (18)	O4W—H8W	0.86 (5)
N10B—H10C	0.885 (18)	O4W'—H7W	1.10 (5)
N10B—H10D	0.860 (18)	O4W'—H8W	0.81 (5)
N3A—C2A—N1A	125.8 (3)	C6B—N10B—H10C	121 (2)
N3A—C2A—H2A	117.1	C6B—N10B—H10D	120 (2)
N1A—C2A—H2A	117.1	H10C—N10B—H10D	119 (3)
N9A—C4A—N3A	127.7 (2)	N13—C12—N11	108.6 (2)
N9A—C4A—C5A	104.7 (2)	N13—C12—H12	125.7
N3A—C4A—C5A	127.5 (2)	N11—C12—H12	125.7
N7A—C5A—C6A	130.4 (3)	C15—C14—N13	107.3 (2)
N7A—C5A—C4A	111.7 (2)	C15—C14—H14	126.4
C6A—C5A—C4A	118.0 (3)	N13—C14—H14	126.4
N10A—C6A—N1A	120.3 (2)	C14—C15—N11	106.8 (2)
N10A—C6A—C5A	126.3 (3)	C14—C15—H15	126.6
N1A—C6A—C5A	113.4 (2)	N11—C15—H15	126.6
N7A—C8A—N9A	114.4 (3)	N11—C16—C17	115.42 (19)
N7A—C8A—H8A	122.8	N11—C16—H16A	108.4
N9A—C8A—H8A	122.8	C17—C16—H16A	108.4
C2A—N1A—C6A	123.6 (2)	N11—C16—H16B	108.4
C2A—N1A—H1A	116 (3)	C17—C16—H16B	108.4
C6A—N1A—H1A	120 (3)	H16A—C16—H16B	107.5
C2A—N3A—C4A	111.5 (3)	O18—C17—C16	107.01 (18)
C8A—N7A—C5A	102.4 (2)	O18—C17—P1	108.49 (15)
C4A—N9A—C8A	106.7 (2)	C16—C17—P1	112.59 (16)
C4A—N9A—H9A	130 (3)	O18—C17—P2	110.47 (15)
C8A—N9A—H9A	124 (3)	C16—C17—P2	104.40 (14)
C6A—N10A—H10A	122 (2)	P1—C17—P2	113.66 (11)
C6A—N10A—H10B	120 (2)	C17—O18—H18	112 (3)
H10A—N10A—H10B	118 (3)	P1—O21—H21	113 (3)
N3B—C2B—N1B	126.4 (3)	C12—N11—C15	108.4 (2)
N3B—C2B—H2B	116.8	C12—N11—C16	124.0 (2)
N1B—C2B—H2B	116.8	C15—N11—C16	127.5 (2)
N9B—C4B—N3B	127.4 (2)	C12—N13—C14	108.9 (2)
N9B—C4B—C5B	104.8 (2)	C12—N13—H13	122 (3)
N3B—C4B—C5B	127.8 (2)	C14—N13—H13	128 (3)
N7B—C5B—C4B	111.5 (2)	O20—P1—O19	116.14 (12)
N7B—C5B—C6B	130.6 (2)	O20—P1—O21	108.74 (11)
C4B—C5B—C6B	117.9 (2)	O19—P1—O21	109.12 (11)
N10B—C6B—N1B	121.0 (2)	O20—P1—C17	109.09 (11)
N10B—C6B—C5B	125.5 (2)	O19—P1—C17	108.61 (10)
N1B—C6B—C5B	113.4 (2)	O21—P1—C17	104.52 (11)
N7B—C8B—N9B	113.9 (2)	O22—P2—O24	111.88 (11)
N7B—C8B—H8B	123.1	O22—P2—O23	111.64 (10)
N9B—C8B—H8B	123.1	O24—P2—O23	113.63 (10)
C2B—N1B—C6B	123.5 (2)	O22—P2—C17	106.41 (10)
C2B—N1B—H1B	117 (2)	O24—P2—C17	105.72 (10)
C6B—N1B—H1B	119 (2)	O23—P2—C17	106.99 (10)
C2B—N3B—C4B	110.8 (2)	H1W—O1W—H2W	103 (3)
C8B—N7B—C5B	102.9 (2)	H3W—O2W—H4W	115 (5)
C4B—N9B—C8B	106.9 (2)	H5W—O3W—H6W	106 (5)
C4B—N9B—H9B	126 (2)	H7W—O4W—H8W	104 (5)
C8B—N9B—H9B	126 (2)	H7W—O4W'—H8W	82 (5)
N9A—C4A—C5A—N7A	0.1 (3)	C4B—C5B—N7B—C8B	0.1 (3)
N3A—C4A—C5A—N7A	180.0 (2)	C6B—C5B—N7B—C8B	−177.8 (3)
N9A—C4A—C5A—C6A	179.1 (2)	N3B—C4B—N9B—C8B	−179.6 (3)
N3A—C4A—C5A—C6A	−1.0 (4)	C5B—C4B—N9B—C8B	0.9 (3)
N7A—C5A—C6A—N10A	−1.0 (5)	N7B—C8B—N9B—C4B	−1.0 (3)
C4A—C5A—C6A—N10A	−179.8 (2)	N13—C14—C15—N11	−0.4 (3)
N7A—C5A—C6A—N1A	177.8 (3)	N11—C16—C17—O18	53.9 (3)
C4A—C5A—C6A—N1A	−1.0 (3)	N11—C16—C17—P1	−65.2 (2)
N3A—C2A—N1A—C6A	−1.4 (5)	N11—C16—C17—P2	171.07 (17)
N10A—C6A—N1A—C2A	−179.0 (3)	N13—C12—N11—C15	−0.3 (3)
C5A—C6A—N1A—C2A	2.2 (4)	N13—C12—N11—C16	−178.0 (2)
N1A—C2A—N3A—C4A	−0.6 (4)	C14—C15—N11—C12	0.4 (3)
N9A—C4A—N3A—C2A	−178.3 (3)	C14—C15—N11—C16	178.1 (2)
C5A—C4A—N3A—C2A	1.8 (4)	C17—C16—N11—C12	−85.5 (3)
N9A—C8A—N7A—C5A	0.6 (3)	C17—C16—N11—C15	97.2 (3)
C6A—C5A—N7A—C8A	−179.3 (3)	N11—C12—N13—C14	0.1 (3)
C4A—C5A—N7A—C8A	−0.4 (3)	C15—C14—N13—C12	0.2 (3)
N3A—C4A—N9A—C8A	−179.6 (3)	O18—C17—P1—O20	−177.50 (15)
C5A—C4A—N9A—C8A	0.3 (3)	C16—C17—P1—O20	−59.26 (18)
N7A—C8A—N9A—C4A	−0.6 (3)	P2—C17—P1—O20	59.20 (15)
N9B—C4B—C5B—N7B	−0.6 (3)	O18—C17—P1—O19	−50.03 (18)
N3B—C4B—C5B—N7B	179.9 (2)	C16—C17—P1—O19	68.21 (18)
N9B—C4B—C5B—C6B	177.5 (2)	P2—C17—P1—O19	−173.33 (12)
N3B—C4B—C5B—C6B	−1.9 (4)	O18—C17—P1—O21	66.34 (16)
N7B—C5B—C6B—N10B	−2.8 (4)	C16—C17—P1—O21	−175.41 (15)
C4B—C5B—C6B—N10B	179.5 (2)	P2—C17—P1—O21	−56.96 (14)
N7B—C5B—C6B—N1B	177.5 (2)	O18—C17—P2—O22	56.58 (17)
C4B—C5B—C6B—N1B	−0.2 (3)	C16—C17—P2—O22	−58.14 (17)
N3B—C2B—N1B—C6B	−0.8 (5)	P1—C17—P2—O22	178.79 (12)
N10B—C6B—N1B—C2B	−178.2 (3)	O18—C17—P2—O24	175.69 (15)
C5B—C6B—N1B—C2B	1.5 (4)	C16—C17—P2—O24	60.96 (17)
N1B—C2B—N3B—C4B	−1.2 (4)	P1—C17—P2—O24	−62.10 (14)
N9B—C4B—N3B—C2B	−176.8 (3)	O18—C17—P2—O23	−62.89 (17)
C5B—C4B—N3B—C2B	2.6 (4)	C16—C17—P2—O23	−177.61 (15)
N9B—C8B—N7B—C5B	0.5 (3)	P1—C17—P2—O23	59.33 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O24^i	0.90 (2)	1.78 (2)	2.615 (3)	154 (4)
N9A—H9A···O22^ii	0.90 (2)	1.72 (2)	2.599 (3)	167 (4)
N10A—H10A···N7B	0.87 (2)	2.09 (2)	2.933 (3)	163 (3)
N10A—H10B···O24^i	0.88 (2)	2.31 (3)	2.990 (3)	135 (3)
N10A—H10B···O20^i	0.88 (2)	2.35 (3)	3.083 (3)	141 (3)
N1B—H1B···O23	0.90 (2)	1.69 (2)	2.585 (3)	179 (3)
N9B—H9B···O1W	0.88 (2)	1.94 (2)	2.810 (3)	174 (3)
N10B—H10C···O21	0.89 (2)	2.03 (2)	2.896 (3)	165 (3)
N10B—H10D···N7A	0.86 (2)	2.15 (2)	2.968 (3)	160 (3)
O18—H18···O1W^iii	0.86 (2)	2.09 (2)	2.940 (3)	169 (4)
O21—H21···O2W	0.86 (2)	1.71 (2)	2.564 (3)	172 (4)
N13—H13···O19^iv	0.89 (2)	1.81 (2)	2.683 (3)	168 (4)
O1W—H1W···O23^v	0.85 (2)	1.96 (2)	2.765 (3)	156 (4)
O1W—H2W···O24^vi	0.86 (2)	1.98 (2)	2.839 (3)	176 (4)
O2W—H3W···O4W′	0.85 (2)	1.91 (3)	2.665 (15)	147 (5)
O2W—H3W···O4W	0.85 (2)	1.90 (3)	2.714 (5)	159 (5)
O2W—H4W···O20^vii	0.85 (2)	1.84 (2)	2.691 (3)	172 (5)
O3W—H5W···O22^viii	0.85 (2)	2.14 (2)	2.971 (3)	165 (6)
O3W—H6W···O20	0.85 (2)	2.34 (3)	3.124 (4)	155 (5)
O3W—H6W···O19	0.85 (2)	2.35 (4)	3.049 (4)	139 (5)
O4W—H7W···O19	0.75 (5)	2.13 (5)	2.787 (4)	148 (5)
O4W—H8W···O23^ii	0.85 (5)	2.16 (5)	2.876 (4)	142 (5)

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+3/2, y−1/2, −z+1/2; (iii) x−1/2, −y+3/2, z+1/2; (iv) −x+2, −y+1, −z+1; (v) x+1/2, −y+3/2, z−1/2; (vi) x−1/2, −y+3/2, z−1/2; (vii) x−1, y, z; (viii) −x+5/2, y−1/2, −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

Crystal data

2C5H6N5^+·C5H8N2O7P2^2^−·6H2O	Z = 2
Mr = 614.43	F(000) = 680
Triclinic, P1	Dx = 1.607 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2742 (6) Å	Cell parameters from 5381 reflections
b = 10.7987 (9) Å	θ = 2.5–27.8°
c = 17.6202 (15) Å	µ = 0.25 mm^−1
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) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	6286 independent reflections
Radiation source: fine-focus sealed tube	5401 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω scan	θmax = 28.0°, θmin = 1.2°
Absorption correction: multi-scan (SABABS; Bruker, 2001)	h = −9→9
Tmin = 0.96, Tmax = 0.99	k = −14→14
15899 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0651P)^2 + 0.7724P] where P = (Fo^2 + 2Fc^2)/3
6286 reflections	(Δ/σ)max = 0.001
478 parameters	Δρmax = 0.54 e Å^−3
44 restraints	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C2A	0.7027 (4)	0.7288 (3)	0.67916 (16)	0.0389 (6)
H2A	0.7323	0.7015	0.7248	0.047*
C4A	0.6641 (4)	0.6977 (2)	0.55138 (14)	0.0318 (5)
C5A	0.6084 (3)	0.8184 (2)	0.55255 (14)	0.0297 (5)
C6A	0.6055 (3)	0.9023 (2)	0.62518 (14)	0.0294 (5)
C8A	0.6090 (4)	0.7271 (3)	0.43473 (16)	0.0427 (7)
H8A	0.5979	0.7107	0.3805	0.051*
N1A	0.6532 (3)	0.8490 (2)	0.68685 (12)	0.0338 (5)
H1A	0.651 (4)	0.892 (3)	0.7336 (12)	0.047 (9)*
N3A	0.7127 (3)	0.6475 (2)	0.61354 (13)	0.0387 (5)
N7A	0.5741 (3)	0.8363 (2)	0.47828 (12)	0.0372 (5)
N9A	0.6624 (4)	0.6405 (2)	0.47547 (13)	0.0393 (5)
H9A	0.698 (5)	0.564 (2)	0.460 (2)	0.072 (12)*
N10A	0.5634 (3)	1.0203 (2)	0.63604 (13)	0.0380 (5)
H10A	0.593 (4)	1.071 (3)	0.6826 (13)	0.050 (9)*
H10B	0.530 (4)	1.046 (3)	0.5930 (14)	0.046 (9)*
C2B	0.7945 (4)	0.3311 (3)	0.36801 (17)	0.0442 (7)
H2B	0.7619	0.3718	0.3281	0.053*
C4B	0.8345 (4)	0.3324 (2)	0.49323 (15)	0.0338 (5)
C5B	0.8874 (4)	0.2095 (2)	0.47870 (15)	0.0321 (5)
C6B	0.8929 (4)	0.1471 (2)	0.40071 (15)	0.0333 (5)
C8B	0.9002 (5)	0.2713 (3)	0.60105 (17)	0.0497 (8)
H8B	0.9171	0.2734	0.6542	0.060*
N1B	0.8443 (4)	0.2124 (2)	0.34539 (13)	0.0410 (5)
H1B	0.8455	0.1780	0.2967	0.049*	0.50
N3B	0.7854 (3)	0.3980 (2)	0.43926 (14)	0.0405 (5)
N7B	0.9286 (4)	0.1717 (2)	0.54750 (13)	0.0430 (6)
N9B	0.8439 (4)	0.3711 (2)	0.57239 (14)	0.0434 (6)
H9B	0.821 (5)	0.445 (2)	0.5964 (19)	0.060 (10)*
N10B	0.9440 (4)	0.0304 (2)	0.37866 (14)	0.0438 (6)
H10C	0.951 (5)	−0.002 (3)	0.3298 (12)	0.056 (10)*
H10D	0.970 (4)	−0.017 (3)	0.4126 (16)	0.047 (9)*
C12	0.7985 (3)	1.4372 (2)	1.03938 (14)	0.0288 (5)
H12	0.8456	1.4028	1.0802	0.035*
C14	0.7287 (4)	1.5725 (2)	0.96816 (16)	0.0362 (6)
H14	0.7200	1.6482	0.9516	0.043*
C15	0.6590 (3)	1.4561 (2)	0.92890 (15)	0.0325 (5)
H15	0.5926	1.4364	0.8802	0.039*
C16	0.6578 (3)	1.2343 (2)	0.95667 (14)	0.0265 (5)
H16A	0.5468	1.2150	0.9210	0.032*
H16B	0.6311	1.2084	1.0044	0.032*
C17	0.8131 (3)	1.15684 (19)	0.92018 (12)	0.0200 (4)
N11	0.7048 (3)	1.37228 (18)	0.97454 (11)	0.0255 (4)
N13	0.8145 (3)	1.5578 (2)	1.03686 (13)	0.0328 (5)
H13	0.875 (4)	1.618 (2)	1.0727 (15)	0.048 (9)*
O18	0.9822 (2)	1.19553 (16)	0.96786 (9)	0.0282 (4)
H18	0.997 (5)	1.150 (3)	0.9998 (16)	0.051 (10)*
O19	0.9798 (2)	1.30606 (16)	0.83553 (10)	0.0328 (4)
O20	0.6725 (2)	1.18517 (17)	0.77726 (10)	0.0335 (4)
O21	0.9583 (2)	1.06948 (17)	0.78296 (10)	0.0324 (4)
H21	1.064 (3)	1.068 (3)	0.8052 (19)	0.059 (11)*
O22	0.6647 (2)	0.97883 (16)	0.99016 (9)	0.0290 (4)
H22	0.5562	0.9957	0.9874	0.044*	0.50
O23	0.9260 (2)	0.91896 (16)	0.91238 (10)	0.0303 (4)
O24	0.6112 (2)	0.93812 (15)	0.84278 (9)	0.0281 (4)
P1	0.85349 (8)	1.18687 (5)	0.82327 (3)	0.02295 (15)
P2	0.74712 (8)	0.98543 (5)	0.91318 (3)	0.02200 (14)
O1W	1.2782 (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)
H1W	1.248 (5)	1.033 (3)	0.8952 (15)	0.066*
H2W	1.362 (4)	1.016 (3)	0.8321 (18)	0.066*
O2W	0.4121 (4)	0.7124 (2)	0.84922 (15)	0.0657 (7)
H3W	0.483 (5)	0.780 (2)	0.846 (2)	0.079*
H4W	0.447 (5)	0.647 (2)	0.814 (2)	0.079*
O3W	0.3260 (4)	0.2868 (3)	0.76294 (19)	0.0728 (8)
H5W	0.403 (4)	0.233 (3)	0.775 (2)	0.087*
H6W	0.232 (4)	0.284 (4)	0.790 (2)	0.087*
O4W	0.8724 (4)	0.4914 (2)	0.75162 (15)	0.0670 (7)
H7W	0.905 (5)	0.428 (2)	0.773 (2)	0.080*
H8W	0.938 (5)	0.561 (2)	0.775 (2)	0.080*
O5W	0.4851 (5)	0.5039 (3)	0.7396 (2)	0.0803 (8)
H9W	0.422 (5)	0.435 (3)	0.747 (3)	0.096*
H10W	0.604 (3)	0.487 (4)	0.741 (3)	0.096*
O6W	0.057 (2)	0.7648 (14)	0.7999 (7)	0.057 (2)	0.50
H12W	0.020 (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
H11W	0.159 (4)	0.741 (5)	0.818 (2)	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2A	0.0464 (16)	0.0419 (15)	0.0311 (13)	0.0071 (12)	0.0005 (11)	0.0140 (11)
C4A	0.0362 (13)	0.0278 (12)	0.0310 (13)	0.0064 (10)	0.0018 (10)	0.0046 (10)
C5A	0.0363 (13)	0.0273 (12)	0.0247 (12)	0.0055 (10)	0.0009 (9)	0.0038 (9)
C6A	0.0307 (12)	0.0303 (12)	0.0259 (12)	0.0029 (10)	0.0006 (9)	0.0038 (9)
C8A	0.0645 (19)	0.0361 (14)	0.0264 (13)	0.0137 (13)	0.0009 (12)	0.0027 (11)
N1A	0.0434 (12)	0.0348 (12)	0.0213 (10)	0.0041 (9)	0.0007 (9)	0.0023 (9)
N3A	0.0516 (14)	0.0324 (12)	0.0332 (12)	0.0110 (10)	0.0015 (10)	0.0080 (9)
N7A	0.0559 (14)	0.0319 (11)	0.0242 (10)	0.0119 (10)	−0.0002 (9)	0.0056 (8)
N9A	0.0583 (15)	0.0275 (11)	0.0309 (11)	0.0143 (10)	0.0043 (10)	0.0010 (9)
N10A	0.0560 (15)	0.0284 (11)	0.0269 (11)	0.0110 (10)	−0.0019 (10)	0.0000 (9)
C2B	0.0592 (18)	0.0402 (15)	0.0378 (15)	0.0191 (13)	0.0066 (13)	0.0140 (12)
C4B	0.0370 (13)	0.0286 (12)	0.0358 (14)	0.0065 (10)	0.0080 (11)	0.0047 (10)
C5B	0.0378 (13)	0.0292 (12)	0.0306 (13)	0.0071 (10)	0.0065 (10)	0.0075 (10)
C6B	0.0376 (14)	0.0333 (13)	0.0301 (13)	0.0096 (10)	0.0075 (10)	0.0063 (10)
C8B	0.075 (2)	0.0427 (17)	0.0323 (15)	0.0149 (15)	0.0055 (14)	0.0074 (12)
N1B	0.0603 (15)	0.0384 (13)	0.0270 (11)	0.0173 (11)	0.0085 (10)	0.0082 (9)
N3B	0.0544 (14)	0.0313 (12)	0.0389 (13)	0.0142 (10)	0.0094 (11)	0.0101 (9)
N7B	0.0616 (16)	0.0379 (13)	0.0310 (12)	0.0149 (11)	0.0048 (11)	0.0079 (10)
N9B	0.0629 (16)	0.0300 (12)	0.0363 (13)	0.0125 (11)	0.0096 (11)	0.0006 (10)
N10B	0.0703 (17)	0.0362 (13)	0.0254 (12)	0.0213 (12)	0.0059 (11)	0.0031 (10)
C12	0.0287 (12)	0.0276 (12)	0.0272 (12)	0.0020 (9)	0.0032 (9)	−0.0006 (9)
C14	0.0366 (14)	0.0268 (13)	0.0460 (15)	0.0058 (10)	0.0071 (11)	0.0074 (11)
C15	0.0344 (13)	0.0329 (13)	0.0299 (12)	0.0070 (10)	0.0013 (10)	0.0055 (10)
C16	0.0285 (11)	0.0210 (11)	0.0273 (11)	−0.0001 (9)	0.0078 (9)	−0.0019 (9)
C17	0.0216 (10)	0.0185 (10)	0.0186 (10)	0.0009 (8)	0.0016 (8)	0.0017 (8)
N11	0.0264 (10)	0.0224 (9)	0.0257 (10)	0.0032 (7)	0.0059 (7)	−0.0005 (7)
N13	0.0310 (11)	0.0255 (10)	0.0367 (12)	−0.0005 (8)	0.0039 (9)	−0.0044 (9)
O18	0.0292 (9)	0.0292 (9)	0.0248 (8)	−0.0039 (7)	−0.0062 (6)	0.0073 (7)
O19	0.0413 (10)	0.0302 (9)	0.0265 (9)	−0.0057 (7)	0.0035 (7)	0.0075 (7)
O20	0.0354 (9)	0.0384 (10)	0.0252 (8)	0.0057 (7)	−0.0032 (7)	0.0050 (7)
O21	0.0348 (10)	0.0362 (10)	0.0236 (8)	0.0080 (8)	0.0056 (7)	−0.0015 (7)
O22	0.0292 (9)	0.0341 (9)	0.0255 (8)	0.0019 (7)	0.0050 (7)	0.0094 (7)
O23	0.0313 (9)	0.0308 (9)	0.0296 (9)	0.0092 (7)	0.0026 (7)	0.0069 (7)
O24	0.0298 (8)	0.0281 (8)	0.0240 (8)	−0.0018 (7)	−0.0014 (6)	0.0030 (6)
P1	0.0266 (3)	0.0244 (3)	0.0169 (3)	0.0017 (2)	0.0020 (2)	0.0024 (2)
P2	0.0247 (3)	0.0200 (3)	0.0204 (3)	0.0012 (2)	0.0009 (2)	0.0031 (2)
O1W	0.0349 (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)
O2W	0.0815 (18)	0.0505 (14)	0.0636 (16)	−0.0160 (13)	0.0101 (13)	0.0133 (12)
O3W	0.0583 (16)	0.0790 (19)	0.097 (2)	0.0192 (14)	0.0278 (15)	0.0445 (16)
O4W	0.096 (2)	0.0481 (14)	0.0605 (16)	0.0103 (14)	0.0016 (14)	0.0212 (12)
O5W	0.087 (2)	0.0682 (19)	0.090 (2)	0.0054 (16)	0.0149 (18)	0.0247 (16)
O6W	0.055 (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)

C2A—N3A	1.303 (4)	C14—H14	0.9300
C2A—N1A	1.347 (3)	C15—N11	1.372 (3)
C2A—H2A	0.9300	C15—H15	0.9300
C4A—N9A	1.347 (3)	C16—N11	1.470 (3)
C4A—N3A	1.355 (3)	C16—C17	1.540 (3)
C4A—C5A	1.383 (3)	C16—H16A	0.9700
C5A—N7A	1.370 (3)	C16—H16B	0.9700
C5A—C6A	1.403 (3)	C17—O18	1.426 (3)
C6A—N10A	1.304 (3)	C17—P1	1.846 (2)
C6A—N1A	1.367 (3)	C17—P2	1.861 (2)
C8A—N7A	1.311 (3)	N13—H13	0.876 (18)
C8A—N9A	1.352 (3)	O18—H18	0.828 (18)
C8A—H8A	0.9300	O19—P1	1.5053 (17)
N1A—H1A	0.857 (18)	O20—P1	1.4911 (17)
N9A—H9A	0.877 (19)	O21—P1	1.5797 (17)
N10A—H10A	0.888 (18)	O21—H21	0.839 (18)
N10A—H10B	0.886 (18)	O22—P2	1.5367 (16)
C2B—N3B	1.316 (4)	O22—H22	0.8200
C2B—N1B	1.337 (3)	O23—P2	1.5202 (17)
C2B—H2B	0.9300	O24—P2	1.5054 (16)
C4B—N3B	1.342 (3)	O1W—H1W	0.835 (18)
C4B—N9B	1.363 (3)	O1W—H2W	0.897 (17)
C4B—C5B	1.378 (3)	O1W'—H1W	0.93 (2)
C5B—N7B	1.378 (3)	O1W'—H2W	0.860 (19)
C5B—C6B	1.399 (3)	O2W—H3W	0.888 (18)
C6B—N10B	1.320 (3)	O2W—H4W	0.893 (18)
C6B—N1B	1.358 (3)	O3W—H5W	0.873 (18)
C8B—N7B	1.307 (4)	O3W—H6W	0.867 (18)
C8B—N9B	1.355 (4)	O4W—H7W	0.882 (18)
C8B—H8B	0.9300	O4W—H8W	0.870 (18)
N1B—H1B	0.8600	O5W—H9W	0.888 (19)
N9B—H9B	0.856 (18)	O5W—H10W	0.895 (19)
N10B—H10C	0.862 (18)	O6W—H12W	0.87 (2)
N10B—H10D	0.887 (18)	O6W—H12'	0.96 (6)
C12—N13	1.312 (3)	O6W—H11W	0.860 (19)
C12—N11	1.322 (3)	O6W'—H12W	1.10 (4)
C12—H12	0.9300	O6W'—H12'	0.88 (2)
C14—C15	1.348 (4)	O6W'—H11W	0.78 (4)
C14—N13	1.364 (4)
N3A—C2A—N1A	125.9 (2)	N13—C12—N11	109.1 (2)
N3A—C2A—H2A	117.0	N13—C12—H12	125.5
N1A—C2A—H2A	117.0	N11—C12—H12	125.5
N9A—C4A—N3A	126.9 (2)	C15—C14—N13	106.9 (2)
N9A—C4A—C5A	105.7 (2)	C15—C14—H14	126.5
N3A—C4A—C5A	127.3 (2)	N13—C14—H14	126.5
N7A—C5A—C4A	110.9 (2)	C14—C15—N11	107.0 (2)
N7A—C5A—C6A	130.9 (2)	C14—C15—H15	126.5
C4A—C5A—C6A	118.1 (2)	N11—C15—H15	126.5
N10A—C6A—N1A	121.1 (2)	N11—C16—C17	113.13 (18)
N10A—C6A—C5A	125.6 (2)	N11—C16—H16A	109.0
N1A—C6A—C5A	113.3 (2)	C17—C16—H16A	109.0
N7A—C8A—N9A	114.2 (2)	N11—C16—H16B	109.0
N7A—C8A—H8A	122.9	C17—C16—H16B	109.0
N9A—C8A—H8A	122.9	H16A—C16—H16B	107.8
C2A—N1A—C6A	123.7 (2)	O18—C17—C16	109.35 (17)
C2A—N1A—H1A	116 (2)	O18—C17—P1	106.21 (14)
C6A—N1A—H1A	120 (2)	C16—C17—P1	111.62 (15)
C2A—N3A—C4A	111.6 (2)	O18—C17—P2	110.80 (14)
C8A—N7A—C5A	103.0 (2)	C16—C17—P2	108.11 (14)
C4A—N9A—C8A	106.2 (2)	P1—C17—P2	110.77 (11)
C4A—N9A—H9A	123 (3)	C12—N11—C15	108.1 (2)
C8A—N9A—H9A	131 (3)	C12—N11—C16	124.8 (2)
C6A—N10A—H10A	119 (2)	C15—N11—C16	127.1 (2)
C6A—N10A—H10B	115 (2)	C12—N13—C14	108.9 (2)
H10A—N10A—H10B	125 (3)	C12—N13—H13	125 (2)
N3B—C2B—N1B	128.6 (3)	C14—N13—H13	126 (2)
N3B—C2B—H2B	115.7	C17—O18—H18	111 (2)
N1B—C2B—H2B	115.7	P1—O21—H21	112 (2)
N3B—C4B—N9B	128.3 (2)	P2—O22—H22	109.5
N3B—C4B—C5B	126.0 (2)	O20—P1—O19	116.79 (10)
N9B—C4B—C5B	105.7 (2)	O20—P1—O21	108.41 (10)
N7B—C5B—C4B	110.7 (2)	O19—P1—O21	109.24 (10)
N7B—C5B—C6B	131.8 (2)	O20—P1—C17	109.44 (10)
C4B—C5B—C6B	117.5 (2)	O19—P1—C17	107.78 (9)
N10B—C6B—N1B	119.0 (2)	O21—P1—C17	104.50 (10)
N10B—C6B—C5B	123.8 (2)	O24—P2—O23	115.30 (10)
N1B—C6B—C5B	117.2 (2)	O24—P2—O22	112.91 (10)
N7B—C8B—N9B	114.1 (3)	O23—P2—O22	107.18 (9)
N7B—C8B—H8B	123.0	O24—P2—C17	108.67 (9)
N9B—C8B—H8B	123.0	O23—P2—C17	106.62 (10)
C2B—N1B—C6B	118.8 (2)	O22—P2—C17	105.55 (10)
C2B—N1B—H1B	120.6	H1W—O1W—H2W	110 (3)
C6B—N1B—H1B	120.6	H1W—O1W'—H2W	105 (3)
C2B—N3B—C4B	111.8 (2)	H3W—O2W—H4W	107 (2)
C8B—N7B—C5B	103.5 (2)	H5W—O3W—H6W	108 (3)
C8B—N9B—C4B	106.0 (2)	H7W—O4W—H8W	109 (3)
C8B—N9B—H9B	130 (2)	H9W—O5W—H10W	107 (3)
C4B—N9B—H9B	124 (2)	H12W—O6W—H11W	111 (3)
C6B—N10B—H10C	120 (2)	H12'—O6W—H11W	103 (5)
C6B—N10B—H10D	122 (2)	H12W—O6W'—H11W	98 (4)
H10C—N10B—H10D	118 (3)	H12'—O6W'—H11W	119 (5)
N9A—C4A—C5A—N7A	−0.5 (3)	C4B—C5B—N7B—C8B	−0.1 (3)
N3A—C4A—C5A—N7A	178.7 (3)	C6B—C5B—N7B—C8B	178.9 (3)
N9A—C4A—C5A—C6A	−177.1 (2)	N7B—C8B—N9B—C4B	0.2 (4)
N3A—C4A—C5A—C6A	2.1 (4)	N3B—C4B—N9B—C8B	−180.0 (3)
N7A—C5A—C6A—N10A	1.5 (5)	C5B—C4B—N9B—C8B	−0.2 (3)
C4A—C5A—C6A—N10A	177.3 (3)	N13—C14—C15—N11	−0.3 (3)
N7A—C5A—C6A—N1A	−178.3 (3)	N11—C16—C17—O18	51.9 (2)
C4A—C5A—C6A—N1A	−2.5 (3)	N11—C16—C17—P1	−65.3 (2)
N3A—C2A—N1A—C6A	0.2 (5)	N11—C16—C17—P2	172.60 (15)
N10A—C6A—N1A—C2A	−178.2 (3)	N13—C12—N11—C15	−0.1 (3)
C5A—C6A—N1A—C2A	1.5 (4)	N13—C12—N11—C16	−179.3 (2)
N1A—C2A—N3A—C4A	−0.8 (4)	C14—C15—N11—C12	0.3 (3)
N9A—C4A—N3A—C2A	178.7 (3)	C14—C15—N11—C16	179.5 (2)
C5A—C4A—N3A—C2A	−0.4 (4)	C17—C16—N11—C12	−85.1 (3)
N9A—C8A—N7A—C5A	0.2 (3)	C17—C16—N11—C15	95.8 (3)
C4A—C5A—N7A—C8A	0.2 (3)	N11—C12—N13—C14	−0.1 (3)
C6A—C5A—N7A—C8A	176.3 (3)	C15—C14—N13—C12	0.3 (3)
N3A—C4A—N9A—C8A	−178.7 (3)	O18—C17—P1—O20	−163.63 (13)
C5A—C4A—N9A—C8A	0.6 (3)	C16—C17—P1—O20	−44.54 (17)
N7A—C8A—N9A—C4A	−0.5 (4)	P2—C17—P1—O20	75.99 (13)
N3B—C4B—C5B—N7B	180.0 (3)	O18—C17—P1—O19	−35.68 (16)
N9B—C4B—C5B—N7B	0.2 (3)	C16—C17—P1—O19	83.42 (17)
N3B—C4B—C5B—C6B	0.8 (4)	P2—C17—P1—O19	−156.06 (11)
N9B—C4B—C5B—C6B	−178.9 (2)	O18—C17—P1—O21	80.44 (15)
N7B—C5B—C6B—N10B	−0.1 (5)	C16—C17—P1—O21	−160.46 (15)
C4B—C5B—C6B—N10B	178.8 (3)	P2—C17—P1—O21	−39.93 (13)
N7B—C5B—C6B—N1B	−179.4 (3)	O18—C17—P2—O24	−160.46 (14)
C4B—C5B—C6B—N1B	−0.5 (4)	C16—C17—P2—O24	79.73 (16)
N3B—C2B—N1B—C6B	0.3 (5)	P1—C17—P2—O24	−42.86 (14)
N10B—C6B—N1B—C2B	−179.3 (3)	O18—C17—P2—O23	−35.60 (16)
C5B—C6B—N1B—C2B	0.0 (4)	C16—C17—P2—O23	−155.41 (14)
N1B—C2B—N3B—C4B	0.0 (5)	P1—C17—P2—O23	82.00 (12)
N9B—C4B—N3B—C2B	179.1 (3)	O18—C17—P2—O22	78.16 (16)
C5B—C4B—N3B—C2B	−0.5 (4)	C16—C17—P2—O22	−41.64 (16)
N9B—C8B—N7B—C5B	−0.1 (4)	P1—C17—P2—O22	−164.24 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O24	0.86 (2)	1.93 (2)	2.755 (3)	161 (3)
N9A—H9A···N3B	0.88 (2)	1.90 (2)	2.775 (3)	173 (4)
N10A—H10A···O20	0.89 (2)	1.88 (2)	2.764 (3)	175 (3)
N10A—H10B···N7A^i	0.89 (2)	2.10 (2)	2.944 (3)	159 (3)
N1B—H1B···O6W^ii	0.86	2.09	2.765 (10)	135
N9B—H9B···N3A	0.86 (2)	2.33 (2)	3.138 (3)	158 (3)
N10B—H10C···O21^iii	0.86 (2)	2.13 (2)	2.974 (3)	166 (3)
N10B—H10D···N7B^iv	0.89 (2)	2.09 (2)	2.929 (3)	157 (3)
N13—H13···O19^v	0.88 (2)	1.87 (2)	2.700 (3)	158 (3)
O18—H18···O23^vi	0.83 (2)	1.92 (2)	2.726 (2)	165 (3)
O21—H21···O1W	0.84 (2)	1.76 (2)	2.599 (4)	176 (4)
O21—H21···O1W′	0.84 (2)	1.72 (4)	2.51 (3)	157 (4)
O22—H22···O22^vii	0.82	1.71	2.500 (3)	162
O1W—H1W···O22^vi	0.83 (3)	2.12 (3)	2.820 (4)	143 (3)
O1W—H2W···O24^viii	0.90 (3)	2.03 (3)	2.837 (4)	148 (3)
O2W—H3W···O24	0.89 (2)	1.91 (2)	2.792 (3)	173 (4)
O2W—H4W···O5W	0.89 (2)	1.85 (2)	2.739 (4)	172 (4)
O3W—H5W···O20^ix	0.87 (2)	2.06 (2)	2.821 (3)	146 (4)
O3W—H6W···O19^x	0.87 (2)	2.06 (2)	2.906 (3)	165 (4)
O4W—H7W···O19^ix	0.88 (2)	1.97 (2)	2.841 (3)	171 (4)
O4W—H8W···O6W^viii	0.87 (2)	2.26 (2)	3.091 (15)	159 (3)
O5W—H9W···O3W	0.89 (2)	1.80 (2)	2.680 (4)	172 (4)
O5W—H10W···O4W	0.90 (2)	1.94 (2)	2.823 (5)	167 (4)
O6W—H11W···O2W	0.85 (3)	1.93 (3)	2.791 (15)	169 (4)
O6W—H12W···O23^xi	0.87 (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, y−1, z; (x) x−1, y−1, z; (xi) x−1, y, z.