Bis[(2,2-dimethyl-propano-yloxy)meth-yl] {[2-(6-amino-9H-purin-9-yl)eth-oxy]meth-yl}phospho-nate-succinic acid (2/1).

The title compound, C(20)H(32)N(5)O(8)P·0.5C(4)H(6)O(4), is composed of two 9-{2-[bis-(pivaloyloxymeth-oxy)phosphinylmeth-oxy]eth-yl}adenine, commonly known as adefovir dipivoxil (AD), mol-ecules linked to the carb-oxy-lic acid groups of succinic acid (SA). The asymmetric unit contains one mol-ecule of AD and half a mol-ecule of SA, which sits on an inversion center. Both adenine units in the two AD mol-ecules make AD-SA N-H⋯O and SA-AD O-H⋯N hydrogen bonds to SA. In addition, the inter-molecular AD-AD N-H⋯O-P hydrogen bond serves to stabilize the cocrystal. There is also a π-π stacking inter-action [inter-planar spacing 3.34 (19) Å] between adjacent inversion-related adenine groups.

Related literature

For the synthesis and process optimization of 9-{2-[bis(pivaloyloxymeth­oxy)phosphinylmeth­oxy]eth­yl}adenine, see: Starrett et al. (1992 ▶); Yu et al. (1999 ▶). For the biological and pharmacological relevance of 9-{2-[bis­(pivaloyloxymeth­oxy)phosphinylmeth­oxy]eth­yl}adenine, see: Qaqish et al. (2003 ▶); Julander et al. (2002 ▶). For the structure of a hydrate of the title compound, see: Chang et al. (2007 ▶).

Experimental

Crystal data

C20H32N5O8P·0.5C4H6O4

M = 560.52

Triclinic,

a = 7.7122 (12) Å

b = 10.1577 (15) Å

c = 19.185 (3) Å

α = 80.409 (8)°

β = 79.718 (9)°

γ = 80.407 (8)°

V = 1443.5 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.15 mm−1

T = 296 K

0.11 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.982, T max = 0.987

49737 measured reflections

7222 independent reflections

4593 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.143

S = 1.01

7222 reflections

417 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812006873/pk2386sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006873/pk2386Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006873/pk2386Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H32N5O8P·0.5C4H6O4	Z = 2
Mr = 560.52	F(000) = 594
Triclinic, P1	Dx = 1.290 Mg m−3
Hall symbol: -P 1	Melting point: 410 K
a = 7.7122 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1577 (15) Å	Cell parameters from 9846 reflections
c = 19.185 (3) Å	θ = 2.2–25.7°
α = 80.409 (8)°	µ = 0.15 mm−1
β = 79.718 (9)°	T = 296 K
γ = 80.407 (8)°	Block, colourless
V = 1443.5 (4) Å3	0.11 × 0.10 × 0.08 mm

Bruker SMART CCD diffractometer	7222 independent reflections
Radiation source: fine-focus sealed tube	4593 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
φ and ω scans	θmax = 28.4°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
Tmin = 0.982, Tmax = 0.987	k = −13→13
49737 measured reflections	l = −25→25

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0783P)2] where P = (Fo2 + 2Fc2)/3
7222 reflections	(Δ/σ)max < 0.001
417 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
P1	0.85354 (6)	0.35488 (4)	0.23364 (3)	0.04127 (14)
O2	1.16908 (15)	0.27477 (11)	0.16611 (7)	0.0465 (3)
H22A	0.869 (3)	−0.400 (2)	0.0252 (13)	0.083 (8)*
O1	0.75924 (17)	0.37739 (12)	0.17242 (7)	0.0520 (3)
H7A	1.410 (3)	0.2107 (19)	0.1924 (10)	0.052 (5)*
N4	1.30471 (18)	−0.10694 (13)	0.07213 (8)	0.0408 (3)
H6A	1.364 (3)	0.2683 (19)	0.0495 (10)	0.050 (5)*
N5	1.40907 (18)	0.07897 (12)	0.08442 (7)	0.0376 (3)
H8A	1.137 (3)	0.353 (2)	0.2554 (13)	0.077 (7)*
O10	1.08166 (19)	−0.23084 (12)	0.01701 (8)	0.0561 (4)
H1C	1.590 (3)	−0.454 (2)	0.1269 (10)	0.047 (5)*
N1	1.5210 (2)	−0.38651 (15)	0.11658 (10)	0.0497 (4)
H5	1.177 (3)	0.0849 (19)	0.0460 (10)	0.054 (5)*
O6	0.79832 (17)	0.45855 (12)	0.28933 (7)	0.0545 (3)
H7B	1.377 (3)	0.371 (2)	0.1459 (10)	0.057 (5)*
O3	0.83198 (18)	0.21639 (11)	0.28310 (7)	0.0526 (3)
H6B	1.549 (3)	0.2239 (18)	0.0706 (10)	0.054 (6)*
C3	1.4627 (2)	−0.14293 (15)	0.09965 (9)	0.0350 (4)
H1A	1.870 (3)	−0.1491 (19)	0.1681 (11)	0.059 (6)*
N2	1.7135 (2)	−0.26489 (14)	0.14725 (9)	0.0508 (4)
H15B	0.551 (3)	0.523 (2)	0.2714 (12)	0.071 (7)*
N3	1.6779 (2)	−0.02193 (14)	0.13207 (9)	0.0513 (4)
H15A	0.633 (3)	0.619 (2)	0.3206 (12)	0.078 (7)*
C4	1.5280 (2)	−0.02841 (15)	0.10754 (9)	0.0372 (4)
H22B	0.974 (3)	−0.383 (2)	−0.0530 (12)	0.065 (6)*
O4	0.9500 (2)	0.00392 (13)	0.25970 (8)	0.0628 (4)
H8B	1.104 (3)	0.456 (2)	0.1946 (12)	0.073 (7)*
O7	0.5407 (2)	0.45750 (14)	0.37225 (8)	0.0645 (4)
C5	1.2792 (2)	0.02556 (16)	0.06432 (10)	0.0415 (4)
C2	1.5646 (2)	−0.26729 (15)	0.12075 (9)	0.0383 (4)
H9B	0.689 (4)	0.071 (3)	0.2924 (16)	0.112 (10)*
C6	1.4277 (3)	0.22069 (16)	0.08249 (11)	0.0438 (4)
H1B	1.438 (3)	−0.3928 (19)	0.0988 (10)	0.044 (6)*
C7	1.3572 (2)	0.27262 (18)	0.15218 (11)	0.0450 (4)
H9A	0.792 (3)	0.126 (2)	0.2055 (14)	0.088 (8)*
C22	0.9785 (3)	−0.42444 (17)	−0.00200 (12)	0.0436 (4)
H10	1.161 (3)	−0.206 (2)	0.0348 (13)	0.081 (8)*
C21	1.1118 (2)	−0.36274 (17)	0.02458 (10)	0.0445 (4)
C8	1.0864 (3)	0.3663 (2)	0.21406 (13)	0.0505 (5)
C1	1.7603 (3)	−0.14515 (19)	0.15018 (13)	0.0577 (5)
O9	1.2352 (2)	−0.42677 (14)	0.05093 (11)	0.0873 (6)
O5	0.8495 (3)	−0.0752 (3)	0.37084 (13)	0.1501 (12)
C9	0.7978 (3)	0.10227 (19)	0.25713 (16)	0.0618 (6)
C11	1.1398 (3)	−0.1700 (2)	0.31830 (12)	0.0678 (6)
C15	0.6237 (3)	0.5252 (2)	0.30718 (14)	0.0625 (6)
O8	0.4230 (3)	0.3366 (2)	0.31153 (9)	0.0959 (6)
C16	0.4436 (3)	0.3614 (2)	0.36752 (12)	0.0608 (5)
C10	0.9642 (3)	−0.0782 (2)	0.32119 (13)	0.0696 (6)
C18	0.2912 (6)	0.3830 (4)	0.4914 (2)	0.1566 (19)
H18A	0.1843	0.4337	0.4764	0.235*
H18B	0.3726	0.4436	0.4936	0.235*
H18C	0.2627	0.3324	0.5379	0.235*
C14	1.2937 (4)	−0.0882 (3)	0.28699 (18)	0.1026 (10)
H14A	1.2850	−0.0523	0.2380	0.154*
H14B	1.4052	−0.1458	0.2894	0.154*
H14C	1.2870	−0.0155	0.3140	0.154*
C12	1.1638 (5)	−0.2356 (4)	0.39287 (18)	0.1525 (18)
H12A	1.1480	−0.1675	0.4235	0.229*
H12B	1.2813	−0.2852	0.3922	0.229*
H12C	1.0774	−0.2960	0.4105	0.229*
C17	0.3749 (4)	0.2886 (3)	0.43929 (13)	0.0794 (7)
C20	0.5398 (7)	0.2122 (6)	0.4705 (3)	0.213 (3)
H20A	0.5030	0.1645	0.5170	0.320*
H20B	0.6162	0.2752	0.4746	0.320*
H20C	0.6030	0.1491	0.4395	0.320*
C19	0.2625 (9)	0.1901 (6)	0.4313 (2)	0.227 (3)
H19A	0.2433	0.1300	0.4754	0.341*
H19B	0.3207	0.1392	0.3937	0.341*
H19C	0.1501	0.2367	0.4198	0.341*
C13	1.1420 (4)	−0.2716 (3)	0.2684 (2)	0.1238 (13)
H13A	1.2543	−0.3294	0.2651	0.186*
H13B	1.1254	−0.2249	0.2217	0.186*
H13C	1.0477	−0.3249	0.2866	0.186*

	U11	U22	U33	U12	U13	U23
P1	0.0401 (3)	0.0328 (2)	0.0502 (3)	0.00576 (17)	−0.0116 (2)	−0.01014 (19)
O2	0.0360 (7)	0.0422 (6)	0.0663 (8)	−0.0040 (5)	−0.0069 (6)	−0.0242 (6)
O1	0.0506 (8)	0.0463 (7)	0.0587 (8)	0.0086 (6)	−0.0214 (6)	−0.0078 (6)
N4	0.0401 (8)	0.0326 (7)	0.0523 (9)	−0.0019 (6)	−0.0169 (7)	−0.0061 (6)
N5	0.0391 (8)	0.0280 (6)	0.0449 (8)	−0.0019 (5)	−0.0073 (6)	−0.0046 (6)
O10	0.0544 (9)	0.0388 (7)	0.0831 (10)	−0.0083 (6)	−0.0301 (8)	−0.0090 (6)
N1	0.0500 (10)	0.0280 (7)	0.0766 (12)	−0.0011 (7)	−0.0322 (9)	−0.0034 (7)
O6	0.0524 (8)	0.0457 (7)	0.0661 (9)	0.0058 (6)	−0.0065 (7)	−0.0249 (6)
O3	0.0654 (9)	0.0379 (6)	0.0564 (8)	−0.0030 (6)	−0.0194 (7)	−0.0062 (6)
C3	0.0367 (9)	0.0315 (8)	0.0377 (9)	−0.0033 (6)	−0.0095 (7)	−0.0054 (6)
N2	0.0493 (9)	0.0369 (8)	0.0724 (11)	0.0008 (6)	−0.0288 (8)	−0.0117 (7)
N3	0.0483 (9)	0.0385 (8)	0.0751 (11)	−0.0039 (7)	−0.0245 (8)	−0.0172 (7)
C4	0.0382 (9)	0.0317 (8)	0.0426 (9)	−0.0018 (6)	−0.0082 (7)	−0.0087 (7)
O4	0.0758 (10)	0.0428 (7)	0.0635 (9)	0.0123 (6)	−0.0158 (8)	−0.0050 (6)
O7	0.0757 (10)	0.0612 (9)	0.0554 (9)	−0.0103 (7)	0.0005 (8)	−0.0159 (7)
C5	0.0416 (10)	0.0335 (8)	0.0498 (10)	−0.0018 (7)	−0.0131 (8)	−0.0042 (7)
C2	0.0400 (9)	0.0340 (8)	0.0420 (9)	−0.0027 (7)	−0.0111 (8)	−0.0058 (7)
C6	0.0421 (11)	0.0283 (8)	0.0588 (12)	−0.0039 (7)	−0.0047 (9)	−0.0038 (8)
C7	0.0353 (10)	0.0356 (9)	0.0676 (13)	−0.0042 (7)	−0.0089 (9)	−0.0167 (9)
C22	0.0392 (10)	0.0415 (9)	0.0544 (12)	−0.0054 (8)	−0.0170 (9)	−0.0090 (8)
C21	0.0420 (10)	0.0397 (9)	0.0553 (11)	−0.0078 (7)	−0.0155 (9)	−0.0066 (8)
C8	0.0455 (11)	0.0486 (11)	0.0624 (13)	−0.0021 (9)	−0.0105 (10)	−0.0245 (10)
C1	0.0504 (12)	0.0462 (10)	0.0869 (16)	0.0009 (9)	−0.0357 (11)	−0.0201 (10)
O9	0.0812 (11)	0.0438 (8)	0.1585 (17)	−0.0067 (7)	−0.0839 (12)	−0.0076 (9)
O5	0.1080 (17)	0.147 (2)	0.1177 (18)	0.0577 (15)	0.0455 (14)	0.0593 (15)
C9	0.0713 (15)	0.0328 (9)	0.0861 (17)	0.0026 (9)	−0.0317 (14)	−0.0108 (10)
C11	0.0641 (14)	0.0598 (13)	0.0673 (14)	0.0139 (11)	−0.0086 (11)	0.0018 (11)
C15	0.0613 (14)	0.0448 (11)	0.0703 (15)	0.0110 (10)	0.0058 (12)	−0.0123 (10)
O8	0.0926 (14)	0.1482 (18)	0.0600 (11)	−0.0470 (12)	−0.0158 (10)	−0.0182 (11)
C16	0.0598 (13)	0.0672 (13)	0.0557 (13)	−0.0030 (10)	−0.0095 (11)	−0.0147 (11)
C10	0.0685 (15)	0.0583 (13)	0.0648 (15)	0.0093 (11)	0.0023 (12)	0.0085 (11)
C18	0.227 (5)	0.119 (3)	0.102 (3)	−0.060 (3)	0.081 (3)	−0.034 (2)
C14	0.0750 (19)	0.108 (2)	0.119 (2)	−0.0001 (16)	−0.0038 (17)	−0.0247 (19)
C12	0.117 (3)	0.192 (4)	0.094 (2)	0.056 (3)	−0.010 (2)	0.051 (2)
C17	0.107 (2)	0.0736 (15)	0.0561 (14)	−0.0243 (15)	0.0029 (14)	−0.0100 (12)
C20	0.201 (5)	0.230 (5)	0.145 (4)	0.024 (4)	−0.028 (4)	0.104 (4)
C19	0.361 (8)	0.261 (6)	0.110 (3)	−0.248 (6)	0.027 (4)	−0.034 (3)
C13	0.095 (2)	0.0793 (19)	0.201 (4)	0.0341 (16)	−0.047 (2)	−0.053 (2)

P1—O1	1.4562 (13)	C22—H22B	1.00 (2)
P1—O3	1.5760 (13)	C21—O9	1.200 (2)
P1—O6	1.5794 (13)	C8—H8A	0.93 (2)
P1—C8	1.787 (2)	C8—H8B	0.95 (2)
O2—C8	1.413 (2)	C1—H1A	0.96 (2)
O2—C7	1.424 (2)	O5—C10	1.179 (3)
N4—C5	1.314 (2)	C9—H9B	1.04 (3)
N4—C3	1.383 (2)	C9—H9A	0.99 (3)
N5—C5	1.354 (2)	C11—C12	1.504 (4)
N5—C4	1.3707 (19)	C11—C10	1.508 (3)
N5—C6	1.464 (2)	C11—C13	1.518 (4)
O10—C21	1.309 (2)	C11—C14	1.538 (4)
O10—H10	0.84 (3)	C15—H15B	0.96 (2)
N1—C2	1.328 (2)	C15—H15A	1.05 (2)
N1—H1C	0.81 (2)	O8—C16	1.186 (3)
N1—H1B	0.79 (2)	C16—C17	1.501 (3)
O6—C15	1.413 (2)	C18—C17	1.490 (4)
O3—C9	1.415 (2)	C18—H18A	0.9600
C3—C4	1.383 (2)	C18—H18B	0.9600
C3—C2	1.411 (2)	C18—H18C	0.9600
N2—C1	1.337 (2)	C14—H14A	0.9600
N2—C2	1.341 (2)	C14—H14B	0.9600
N3—C1	1.327 (2)	C14—H14C	0.9600
N3—C4	1.338 (2)	C12—H12A	0.9600
O4—C10	1.337 (2)	C12—H12B	0.9600
O4—C9	1.411 (2)	C12—H12C	0.9600
O7—C16	1.349 (3)	C17—C19	1.471 (5)
O7—C15	1.420 (3)	C17—C20	1.539 (5)
C5—H5	0.990 (19)	C20—H20A	0.9600
C6—C7	1.497 (3)	C20—H20B	0.9600
C6—H6A	0.90 (2)	C20—H20C	0.9600
C6—H6B	0.93 (2)	C19—H19A	0.9600
C7—H7A	1.012 (19)	C19—H19B	0.9600
C7—H7B	1.02 (2)	C19—H19C	0.9600
C22—C21	1.490 (2)	C13—H13A	0.9600
C22—C22i	1.507 (3)	C13—H13B	0.9600
C22—H22A	0.93 (3)	C13—H13C	0.9600
O1—P1—O3	113.85 (8)	O3—C9—H9B	104.5 (16)
O1—P1—O6	117.52 (7)	O4—C9—H9A	103.8 (15)
O3—P1—O6	101.92 (8)	O3—C9—H9A	108.4 (14)
O1—P1—C8	116.19 (10)	H9B—C9—H9A	120 (2)
O3—P1—C8	106.95 (9)	C12—C11—C10	109.1 (2)
O6—P1—C8	98.37 (8)	C12—C11—C13	112.7 (3)
C8—O2—C7	111.57 (13)	C10—C11—C13	108.6 (2)
C5—N4—C3	104.30 (13)	C12—C11—C14	109.0 (3)
C5—N5—C4	105.98 (13)	C10—C11—C14	110.11 (19)
C5—N5—C6	129.31 (15)	C13—C11—C14	107.4 (2)
C4—N5—C6	124.70 (15)	O6—C15—O7	109.46 (17)
C21—O10—H10	106.4 (17)	O6—C15—H15B	111.4 (14)
C2—N1—H1C	118.2 (13)	O7—C15—H15B	106.6 (14)
C2—N1—H1B	121.6 (14)	O6—C15—H15A	108.1 (13)
H1C—N1—H1B	119.5 (19)	O7—C15—H15A	103.0 (13)
C15—O6—P1	124.52 (15)	H15B—C15—H15A	117.8 (18)
C9—O3—P1	122.53 (14)	O8—C16—O7	121.8 (2)
C4—C3—N4	109.79 (13)	O8—C16—C17	125.3 (2)
C4—C3—C2	116.20 (15)	O7—C16—C17	112.77 (19)
N4—C3—C2	134.00 (15)	O5—C10—O4	121.8 (2)
C1—N2—C2	118.43 (15)	O5—C10—C11	125.9 (2)
C1—N3—C4	110.16 (15)	O4—C10—C11	112.3 (2)
N3—C4—N5	126.26 (14)	C17—C18—H18A	109.5
N3—C4—C3	127.50 (14)	C17—C18—H18B	109.5
N5—C4—C3	106.24 (14)	H18A—C18—H18B	109.5
C10—O4—C9	117.94 (19)	C17—C18—H18C	109.5
C16—O7—C15	117.27 (18)	H18A—C18—H18C	109.5
N4—C5—N5	113.69 (15)	H18B—C18—H18C	109.5
N4—C5—H5	125.8 (11)	C11—C14—H14A	109.5
N5—C5—H5	120.5 (11)	C11—C14—H14B	109.5
N1—C2—N2	118.11 (15)	H14A—C14—H14B	109.5
N1—C2—C3	123.89 (16)	C11—C14—H14C	109.5
N2—C2—C3	118.00 (14)	H14A—C14—H14C	109.5
N5—C6—C7	113.36 (15)	H14B—C14—H14C	109.5
N5—C6—H6A	106.7 (12)	C11—C12—H12A	109.5
C7—C6—H6A	108.1 (12)	C11—C12—H12B	109.5
N5—C6—H6B	104.9 (12)	H12A—C12—H12B	109.5
C7—C6—H6B	110.5 (12)	C11—C12—H12C	109.5
H6A—C6—H6B	113.5 (17)	H12A—C12—H12C	109.5
O2—C7—C6	108.72 (15)	H12B—C12—H12C	109.5
O2—C7—H7A	108.3 (11)	C19—C17—C18	114.6 (3)
C6—C7—H7A	110.1 (10)	C19—C17—C16	110.5 (3)
O2—C7—H7B	105.4 (11)	C18—C17—C16	112.3 (2)
C6—C7—H7B	107.8 (11)	C19—C17—C20	108.7 (4)
H7A—C7—H7B	116.2 (15)	C18—C17—C20	104.0 (4)
C21—C22—C22i	113.30 (19)	C16—C17—C20	106.1 (3)
C21—C22—H22A	106.6 (15)	C17—C20—H20A	109.5
C22i—C22—H22A	111.2 (15)	C17—C20—H20B	109.5
C21—C22—H22B	107.6 (12)	H20A—C20—H20B	109.5
C22i—C22—H22B	109.4 (12)	C17—C20—H20C	109.5
H22A—C22—H22B	108.6 (18)	H20A—C20—H20C	109.5
O9—C21—O10	122.58 (16)	H20B—C20—H20C	109.5
O9—C21—C22	123.77 (16)	C17—C19—H19A	109.5
O10—C21—C22	113.65 (15)	C17—C19—H19B	109.5
O2—C8—P1	108.92 (13)	H19A—C19—H19B	109.5
O2—C8—H8A	112.5 (14)	C17—C19—H19C	109.5
P1—C8—H8A	111.6 (15)	H19A—C19—H19C	109.5
O2—C8—H8B	111.4 (14)	H19B—C19—H19C	109.5
P1—C8—H8B	109.8 (14)	C11—C13—H13A	109.5
H8A—C8—H8B	102.5 (19)	C11—C13—H13B	109.5
N3—C1—N2	129.67 (18)	H13A—C13—H13B	109.5
N3—C1—H1A	115.2 (12)	C11—C13—H13C	109.5
N2—C1—H1A	115.1 (12)	H13A—C13—H13C	109.5
O4—C9—O3	107.72 (17)	H13B—C13—H13C	109.5
O4—C9—H9B	111.6 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1ii	0.812 (19)	2.14 (2)	2.941 (2)	170.16 (18)
N1—H1B···O9	0.79 (2)	2.05 (2)	2.842 (2)	175 (2)
O10—H10···N4	0.84 (2)	1.91 (2)	2.734 (2)	166 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O1i	0.812 (19)	2.14 (2)	2.941 (2)	170.16 (18)
N1—H1B⋯O9	0.79 (2)	2.05 (2)	2.842 (2)	175 (2)
O10—H10⋯N4	0.84 (2)	1.91 (2)	2.734 (2)	166 (2)

Symmetry code: (i) .