9-{2-[Bis(pivaloyloxymeth­oxy)phosphinylmeth­oxy]eth­yl}adenine dihydrate

In the title compound, C₂₀H₃₂N₅O₈P·2H₂O, mol­ecules are linked to each other via inter­molecular N—H...O, N—H...N, O—H...O and O—H...N hydrogen bonds with the water mol­ecules acting as both acceptors and donors.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.073
• wR factor = 0.146
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)        3000 Deg.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: DENZO (Otwinowski & Minor, 1997); cell refinement: SCALE (Otwinowski & Minor, 1997); data reduction: SCALE; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

9-{2-[Bis(pivaloyloxymethoxy)phosphinylmethoxy]ethyl}adenine dihydrate

Crystal data

C20H32N5O8P·2H2O	Z = 2
Mr = 537.51	F(000) = 572
Triclinic, P1	Dx = 1.302 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0590 (12) Å	Cell parameters from 4874 reflections
b = 11.221 (2) Å	θ = 2.2–25.5°
c = 20.972 (4) Å	µ = 0.16 mm^−1
α = 93.88 (3)°	T = 295 K
β = 97.49 (3)°	Block, colourless
γ = 102.97 (3)°	0.60 × 0.40 × 0.40 mm
V = 1370.7 (5) Å^3

Data collection

MAC DIP 2030K diffractometer	3870 reflections with I > 2σ(I)
Radiation source: rotate anode	Rint = 0.048
Graphite monochromator	θmax = 25.5°, θmin = 2.2°
ω scans	h = 0→6
4874 measured reflections	k = −13→13
4873 independent reflections	l = −25→25

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.073	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.146	w = 1/[σ^2(Fo^2) + (0.0129P)^2 + 3.1097P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
4873 reflections	Δρmax = 0.26 e Å^−3
338 parameters	Δρmin = −0.37 e Å^−3
6 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0088 (10)

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
P1	0.75341 (16)	0.97471 (8)	0.23621 (4)	0.0436 (2)
O1	0.5946 (5)	0.8015 (3)	0.30524 (14)	0.0668 (8)
O2	0.9603 (4)	1.0277 (3)	0.28273 (12)	0.0597 (7)
O3	0.5472 (4)	1.0370 (2)	0.24088 (13)	0.0564 (7)
O4	0.6831 (4)	1.2485 (2)	0.26641 (13)	0.0538 (7)
O5	0.3871 (5)	1.2529 (3)	0.19149 (19)	0.0882 (11)
O6	0.7855 (4)	0.9847 (3)	0.16328 (12)	0.0576 (7)
O7	1.0203 (5)	0.9437 (2)	0.08986 (12)	0.0600 (7)
O8	1.0841 (6)	0.7989 (3)	0.15323 (14)	0.0726 (9)
N1	0.3901 (5)	0.2943 (3)	0.40129 (14)	0.0474 (7)
N2	0.2308 (5)	0.4655 (3)	0.37057 (16)	0.0543 (8)
N3	0.7956 (5)	0.5952 (3)	0.45640 (15)	0.0489 (7)
N4	0.4979 (5)	0.6617 (3)	0.40835 (14)	0.0478 (7)
N5	0.7522 (5)	0.3167 (3)	0.45867 (15)	0.0537 (8)
H5A	0.7280	0.2380	0.4572	0.064*
H5B	0.8806	0.3621	0.4779	0.064*
C1	0.5904 (6)	0.3685 (3)	0.43117 (16)	0.0434 (8)
C2	0.2279 (7)	0.3469 (4)	0.37362 (19)	0.0568 (10)
H2C	0.0937	0.2923	0.3536	0.068*
C3	0.4331 (6)	0.5350 (3)	0.40107 (16)	0.0439 (8)
C4	0.7140 (7)	0.6912 (3)	0.44195 (18)	0.0534 (9)
H4A	0.7967	0.7718	0.4537	0.064*
C5	0.6147 (6)	0.4960 (3)	0.43082 (16)	0.0433 (8)
C6	0.3599 (7)	0.7461 (4)	0.3851 (2)	0.0602 (10)
H6A	0.4199	0.8264	0.4090	0.072*
H6B	0.2034	0.7162	0.3927	0.072*
C7	0.3626 (7)	0.7573 (4)	0.3141 (2)	0.0590 (10)
H7A	0.2985	0.6779	0.2895	0.071*
H7B	0.2720	0.8141	0.2994	0.071*
C8	0.6271 (7)	0.8168 (3)	0.24040 (19)	0.0571 (10)
H8A	0.4814	0.7923	0.2121	0.069*
H8B	0.7267	0.7663	0.2269	0.069*
C9	0.5557 (7)	1.1388 (3)	0.2865 (2)	0.0564 (10)
H9A	0.4015	1.1466	0.2900	0.068*
H9B	0.6271	1.1251	0.3287	0.068*
C10	0.5739 (7)	1.2998 (3)	0.2189 (2)	0.0537 (9)
C11	0.7212 (6)	1.4214 (3)	0.20564 (18)	0.0598 (9)
C12	0.6020 (8)	1.4683 (5)	0.1465 (2)	0.0805 (14)
H12A	0.5870	1.4111	0.1092	0.121*
H12B	0.6917	1.5470	0.1393	0.121*
H12C	0.4529	1.4762	0.1542	0.121*
C13	0.9561 (8)	1.4044 (4)	0.1939 (2)	0.0755 (13)
H13A	0.9389	1.3482	0.1560	0.113*
H13B	1.0255	1.3720	0.2305	0.113*
H13C	1.0514	1.4822	0.1878	0.113*
C14	0.7479 (8)	1.5118 (4)	0.2660 (2)	0.0659 (11)
H14A	0.6000	1.5226	0.2731	0.099*
H14B	0.8433	1.5896	0.2597	0.099*
H14C	0.8172	1.4799	0.3028	0.099*
C15	1.0084 (7)	1.0212 (4)	0.1449 (2)	0.0603 (11)
H15A	1.0366	1.1060	0.1350	0.072*
H15B	1.1242	1.0148	0.1802	0.072*
C16	1.0733 (7)	0.8336 (4)	0.10061 (19)	0.0528 (9)
C17	1.1098 (7)	0.7685 (4)	0.0388 (2)	0.0709 (10)
C18	1.2884 (8)	0.8558 (5)	0.0072 (2)	0.0809 (14)
H18A	1.4318	0.8775	0.0357	0.121*
H18B	1.2364	0.9288	−0.0011	0.121*
H18C	1.3085	0.8155	−0.0328	0.121*
C19	0.8825 (8)	0.7325 (5)	−0.0069 (2)	0.0875 (16)
H19A	0.8318	0.8051	−0.0169	0.131*
H19B	0.7700	0.6801	0.0134	0.131*
H19C	0.9030	0.6895	−0.0460	0.131*
C20	1.1993 (11)	0.6558 (5)	0.0550 (3)	0.0978 (18)
H20A	1.3418	0.6811	0.0838	0.147*
H20B	1.2227	0.6137	0.0159	0.147*
H20C	1.0896	0.6016	0.0754	0.147*
OA	0.1519 (6)	0.0473 (3)	0.41309 (15)	0.0782 (9)
H1A	0.074 (7)	0.026 (4)	0.3769 (11)	0.094*
H1B	0.259 (6)	0.104 (3)	0.409 (2)	0.094*
OB	0.7432 (7)	0.0551 (4)	0.4682 (2)	0.0882 (11)
H2A	0.759 (8)	0.030 (5)	0.5042 (13)	0.106*
H2B	0.860 (5)	0.059 (5)	0.452 (2)	0.106*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0494 (5)	0.0384 (5)	0.0415 (5)	0.0099 (4)	0.0029 (4)	0.0019 (4)
O1	0.0658 (18)	0.0654 (19)	0.0608 (18)	−0.0022 (14)	0.0022 (14)	0.0221 (14)
O2	0.0532 (16)	0.0731 (19)	0.0444 (15)	0.0048 (13)	−0.0022 (12)	−0.0006 (13)
O3	0.0604 (16)	0.0372 (14)	0.0703 (18)	0.0172 (12)	0.0031 (13)	−0.0100 (12)
O4	0.0615 (16)	0.0340 (13)	0.0620 (17)	0.0071 (11)	0.0024 (13)	0.0053 (12)
O5	0.0539 (19)	0.0597 (19)	0.138 (3)	0.0010 (15)	−0.0161 (19)	0.018 (2)
O6	0.0549 (16)	0.0676 (18)	0.0454 (15)	0.0051 (13)	0.0049 (12)	0.0075 (13)
O7	0.0800 (19)	0.0565 (17)	0.0484 (15)	0.0230 (14)	0.0152 (14)	0.0064 (13)
O8	0.093 (2)	0.077 (2)	0.0554 (18)	0.0306 (18)	0.0114 (16)	0.0180 (16)
N1	0.0485 (17)	0.0422 (17)	0.0480 (17)	0.0080 (13)	0.0009 (14)	0.0023 (13)
N2	0.0482 (18)	0.053 (2)	0.059 (2)	0.0113 (15)	0.0008 (15)	0.0081 (15)
N3	0.0467 (17)	0.0441 (17)	0.0533 (18)	0.0081 (14)	0.0033 (14)	0.0023 (14)
N4	0.0568 (19)	0.0423 (17)	0.0467 (17)	0.0140 (14)	0.0096 (14)	0.0102 (13)
N5	0.0561 (19)	0.0424 (17)	0.059 (2)	0.0127 (14)	−0.0037 (15)	0.0033 (14)
C1	0.052 (2)	0.0417 (19)	0.0370 (18)	0.0127 (16)	0.0066 (15)	0.0032 (15)
C2	0.055 (2)	0.051 (2)	0.056 (2)	0.0023 (18)	−0.0039 (18)	0.0033 (18)
C3	0.054 (2)	0.0426 (19)	0.0364 (18)	0.0132 (16)	0.0056 (15)	0.0059 (15)
C4	0.063 (2)	0.042 (2)	0.052 (2)	0.0101 (18)	0.0028 (18)	0.0029 (17)
C5	0.046 (2)	0.044 (2)	0.0394 (18)	0.0108 (15)	0.0057 (15)	0.0024 (15)
C6	0.069 (3)	0.054 (2)	0.067 (3)	0.031 (2)	0.013 (2)	0.014 (2)
C7	0.057 (2)	0.050 (2)	0.072 (3)	0.0178 (19)	0.002 (2)	0.016 (2)
C8	0.076 (3)	0.0352 (19)	0.059 (2)	0.0109 (18)	0.006 (2)	0.0095 (17)
C9	0.073 (3)	0.037 (2)	0.062 (2)	0.0146 (18)	0.021 (2)	−0.0031 (17)
C10	0.052 (2)	0.038 (2)	0.070 (3)	0.0125 (17)	0.0033 (19)	0.0026 (18)
C11	0.0555 (18)	0.0473 (18)	0.077 (2)	0.0113 (14)	0.0060 (15)	0.0080 (16)
C12	0.077 (3)	0.084 (3)	0.079 (3)	0.017 (3)	−0.003 (3)	0.027 (3)
C13	0.074 (3)	0.076 (3)	0.085 (3)	0.021 (2)	0.030 (3)	0.019 (3)
C14	0.078 (3)	0.042 (2)	0.079 (3)	0.017 (2)	0.011 (2)	0.002 (2)
C15	0.071 (3)	0.049 (2)	0.058 (2)	0.0022 (19)	0.022 (2)	−0.0003 (19)
C16	0.053 (2)	0.054 (2)	0.049 (2)	0.0085 (18)	0.0043 (17)	0.0061 (18)
C17	0.076 (2)	0.069 (2)	0.078 (2)	0.0248 (18)	0.0219 (18)	0.0068 (18)
C18	0.081 (3)	0.085 (3)	0.084 (3)	0.020 (3)	0.038 (3)	0.009 (3)
C19	0.074 (3)	0.104 (4)	0.072 (3)	0.010 (3)	0.006 (3)	−0.026 (3)
C20	0.133 (5)	0.078 (4)	0.101 (4)	0.054 (4)	0.034 (4)	0.012 (3)
OA	0.087 (2)	0.069 (2)	0.064 (2)	−0.0063 (17)	−0.0066 (17)	0.0173 (17)
OB	0.103 (3)	0.076 (2)	0.100 (3)	0.041 (2)	0.021 (2)	0.028 (2)

Geometric parameters (Å, º)

P1—O2	1.465 (3)	C8—H8B	0.9700
P1—O3	1.573 (3)	C9—H9A	0.9700
P1—O6	1.575 (3)	C9—H9B	0.9700
P1—C8	1.778 (4)	C10—C11	1.517 (5)
O1—C8	1.416 (5)	C11—C13	1.526 (5)
O1—C7	1.423 (5)	C11—C14	1.535 (5)
O3—C9	1.427 (4)	C11—C12	1.537 (5)
O4—C10	1.357 (4)	C12—H12A	0.9600
O4—C9	1.421 (4)	C12—H12B	0.9600
O5—C10	1.188 (5)	C12—H12C	0.9600
O6—C15	1.432 (5)	C13—H13A	0.9600
O7—C16	1.370 (5)	C13—H13B	0.9600
O7—C15	1.417 (4)	C13—H13C	0.9600
O8—C16	1.194 (4)	C14—H14A	0.9600
N1—C2	1.345 (5)	C14—H14B	0.9600
N1—C1	1.355 (4)	C14—H14C	0.9600
N2—C2	1.333 (5)	C15—H15A	0.9700
N2—C3	1.349 (5)	C15—H15B	0.9700
N3—C4	1.319 (5)	C16—C17	1.510 (5)
N3—C5	1.395 (4)	C17—C20	1.526 (6)
N4—C4	1.361 (5)	C17—C19	1.527 (6)
N4—C3	1.379 (4)	C17—C18	1.540 (6)
N4—C6	1.465 (4)	C18—H18A	0.9600
N5—C1	1.336 (4)	C18—H18B	0.9600
N5—H5A	0.8600	C18—H18C	0.9600
N5—H5B	0.8600	C19—H19A	0.9600
C1—C5	1.406 (5)	C19—H19B	0.9600
C2—H2C	0.9300	C19—H19C	0.9600
C3—C5	1.365 (5)	C20—H20A	0.9600
C4—H4A	0.9300	C20—H20B	0.9600
C6—C7	1.505 (6)	C20—H20C	0.9600
C6—H6A	0.9700	OA—H1A	0.83 (3)
C6—H6B	0.9700	OA—H1B	0.82 (4)
C7—H7A	0.9700	OB—H2A	0.83 (3)
C7—H7B	0.9700	OB—H2B	0.82 (4)
C8—H8A	0.9700
O2—P1—O3	115.52 (16)	O4—C10—C11	111.4 (3)
O2—P1—O6	114.60 (15)	C10—C11—C13	109.7 (3)
O3—P1—O6	101.49 (15)	C10—C11—C14	107.1 (3)
O2—P1—C8	115.71 (19)	C13—C11—C14	109.7 (3)
O3—P1—C8	102.77 (18)	C10—C11—C12	109.4 (3)
O6—P1—C8	104.97 (17)	C13—C11—C12	110.5 (4)
C8—O1—C7	114.7 (3)	C14—C11—C12	110.3 (3)
C9—O3—P1	123.6 (3)	C11—C12—H12A	109.5
C10—O4—C9	116.7 (3)	C11—C12—H12B	109.5
C15—O6—P1	121.3 (2)	H12A—C12—H12B	109.5
C16—O7—C15	117.0 (3)	C11—C12—H12C	109.5
C2—N1—C1	118.3 (3)	H12A—C12—H12C	109.5
C2—N2—C3	109.6 (3)	H12B—C12—H12C	109.5
C4—N3—C5	103.0 (3)	C11—C13—H13A	109.5
C4—N4—C3	105.8 (3)	C11—C13—H13B	109.5
C4—N4—C6	127.5 (3)	H13A—C13—H13B	109.5
C3—N4—C6	126.6 (3)	C11—C13—H13C	109.5
C1—N5—H5A	120.0	H13A—C13—H13C	109.5
C1—N5—H5B	120.0	H13B—C13—H13C	109.5
H5A—N5—H5B	120.0	C11—C14—H14A	109.5
N5—C1—N1	118.5 (3)	C11—C14—H14B	109.5
N5—C1—C5	124.1 (3)	H14A—C14—H14B	109.5
N1—C1—C5	117.4 (3)	C11—C14—H14C	109.5
N2—C2—N1	129.7 (4)	H14A—C14—H14C	109.5
N2—C2—H2C	115.2	H14B—C14—H14C	109.5
N1—C2—H2C	115.2	O7—C15—O6	109.0 (3)
N2—C3—C5	127.8 (3)	O7—C15—H15A	109.9
N2—C3—N4	126.3 (3)	O6—C15—H15A	109.9
C5—C3—N4	105.9 (3)	O7—C15—H15B	109.9
N3—C4—N4	114.0 (3)	O6—C15—H15B	109.9
N3—C4—H4A	123.0	H15A—C15—H15B	108.3
N4—C4—H4A	123.0	O8—C16—O7	121.2 (4)
C3—C5—N3	111.2 (3)	O8—C16—C17	127.6 (4)
C3—C5—C1	117.3 (3)	O7—C16—C17	111.1 (3)
N3—C5—C1	131.5 (3)	C16—C17—C20	108.9 (4)
N4—C6—C7	111.0 (3)	C16—C17—C19	108.7 (3)
N4—C6—H6A	109.4	C20—C17—C19	111.3 (4)
C7—C6—H6A	109.4	C16—C17—C18	109.3 (4)
N4—C6—H6B	109.4	C20—C17—C18	109.1 (4)
C7—C6—H6B	109.4	C19—C17—C18	109.6 (4)
H6A—C6—H6B	108.0	C17—C18—H18A	109.5
O1—C7—C6	107.5 (3)	C17—C18—H18B	109.5
O1—C7—H7A	110.2	H18A—C18—H18B	109.5
C6—C7—H7A	110.2	C17—C18—H18C	109.5
O1—C7—H7B	110.2	H18A—C18—H18C	109.5
C6—C7—H7B	110.2	H18B—C18—H18C	109.5
H7A—C7—H7B	108.5	C17—C19—H19A	109.5
O1—C8—P1	107.8 (3)	C17—C19—H19B	109.5
O1—C8—H8A	110.2	H19A—C19—H19B	109.5
P1—C8—H8A	110.2	C17—C19—H19C	109.5
O1—C8—H8B	110.2	H19A—C19—H19C	109.5
P1—C8—H8B	110.2	H19B—C19—H19C	109.5
H8A—C8—H8B	108.5	C17—C20—H20A	109.5
O4—C9—O3	109.9 (3)	C17—C20—H20B	109.5
O4—C9—H9A	109.7	H20A—C20—H20B	109.5
O3—C9—H9A	109.7	C17—C20—H20C	109.5
O4—C9—H9B	109.7	H20A—C20—H20C	109.5
O3—C9—H9B	109.7	H20B—C20—H20C	109.5
H9A—C9—H9B	108.2	H1A—OA—H1B	107 (2)
O5—C10—O4	123.0 (4)	H2A—OB—H2B	110 (3)
O5—C10—C11	125.6 (4)
O2—P1—O3—C9	0.4 (3)	C4—N4—C6—C7	101.3 (4)
O6—P1—O3—C9	−124.2 (3)	C3—N4—C6—C7	−79.5 (5)
C8—P1—O3—C9	127.3 (3)	C8—O1—C7—C6	179.7 (3)
O2—P1—O6—C15	11.3 (3)	N4—C6—C7—O1	−59.2 (4)
O3—P1—O6—C15	136.5 (3)	C7—O1—C8—P1	119.1 (3)
C8—P1—O6—C15	−116.8 (3)	O2—P1—C8—O1	52.4 (3)
C2—N1—C1—N5	−179.9 (3)	O3—P1—C8—O1	−74.5 (3)
C2—N1—C1—C5	−0.3 (5)	O6—P1—C8—O1	179.7 (3)
C3—N2—C2—N1	0.0 (6)	C10—O4—C9—O3	78.1 (4)
C1—N1—C2—N2	−0.2 (6)	P1—O3—C9—O4	76.5 (4)
C2—N2—C3—C5	0.6 (5)	C9—O4—C10—O5	−5.1 (6)
C2—N2—C3—N4	−179.4 (3)	C9—O4—C10—C11	175.4 (3)
C4—N4—C3—N2	−180.0 (3)	O5—C10—C11—C13	−127.3 (5)
C6—N4—C3—N2	0.6 (6)	O4—C10—C11—C13	52.2 (4)
C4—N4—C3—C5	0.0 (4)	O5—C10—C11—C14	113.8 (5)
C6—N4—C3—C5	−179.4 (3)	O4—C10—C11—C14	−66.8 (4)
C5—N3—C4—N4	−1.1 (4)	O5—C10—C11—C12	−5.9 (6)
C3—N4—C4—N3	0.7 (4)	O4—C10—C11—C12	173.6 (3)
C6—N4—C4—N3	−179.9 (3)	C16—O7—C15—O6	−84.2 (4)
N2—C3—C5—N3	179.3 (3)	P1—O6—C15—O7	136.3 (3)
N4—C3—C5—N3	−0.7 (4)	C15—O7—C16—O8	7.9 (6)
N2—C3—C5—C1	−1.1 (6)	C15—O7—C16—C17	−172.7 (3)
N4—C3—C5—C1	179.0 (3)	O8—C16—C17—C20	−8.3 (6)
C4—N3—C5—C3	1.1 (4)	O7—C16—C17—C20	172.4 (4)
C4—N3—C5—C1	−178.5 (4)	O8—C16—C17—C19	113.1 (5)
N5—C1—C5—C3	−179.6 (3)	O7—C16—C17—C19	−66.2 (4)
N1—C1—C5—C3	0.8 (5)	O8—C16—C17—C18	−127.3 (5)
N5—C1—C5—N3	0.0 (6)	O7—C16—C17—C18	53.4 (5)
N1—C1—C5—N3	−179.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···OB	0.86	2.10	2.945 (5)	166
N5—H5B···N3^i	0.86	2.18	2.988 (4)	156
OA—H1A···O2^ii	0.83 (3)	2.01 (2)	2.801 (4)	160 (4)
OA—H1B···N1	0.82 (4)	2.12 (3)	2.867 (4)	150 (5)
OB—H2A···OA^iii	0.83 (3)	2.06 (4)	2.867 (5)	169 (5)
OB—H2B···OA^iv	0.82 (4)	2.07 (3)	2.882 (5)	174 (6)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1, y−1, z; (iii) −x+1, −y, −z+1; (iv) x+1, y, z.