9-(1,1-Dimethyl-3-oxobut-yl)adenine.

The title compound, C(11)H(15)N(5)O, crystallizes with two independent mol-ecules in the asymmetric unit, both of which contain essentially planar imidazole and pyrimidine rings [maximum deviations = 0.002 (2) and 0.026 (2) Å, respectively, for the first mol-ecule, and 0.001 (2) and 0.025 (2) Å for the second]; the dihedral angles between the rings are 2.1 (2) and 1.7 (2)° in the two mol-ecules. The crystal structure is stabilized by inter-molecular N-H⋯N hydrogen bonds, defining chains along a, which are further linked by weak inter-molecular π-π contacts [centroid centroid distance = 3.7989 (16) Å] into planes parallel to (01).

Related literature

For the synthesis of the title compound, see: Jiang & Tang (1995 ▶). For the biological activity of related compounds, see: Jeffery et al. (2000 ▶); Bayes et al. (2003 ▶). For related structures, see: Bo et al. (2006 ▶); Deng et al. (1995 ▶); Wei et al. (2007 ▶); Yu et al. (1990 ▶).

Experimental

Crystal data

C11H15N5O

M = 233.28

Triclinic,

a = 8.2565 (8) Å

b = 11.2229 (11) Å

c = 13.4021 (13) Å

α = 78.421 (1)°

β = 89.551 (2)°

γ = 88.483 (1)°

V = 1216.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.48 × 0.47 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.96, T max = 0.99

6288 measured reflections

4208 independent reflections

2538 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.162

S = 1.06

4208 reflections

313 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034628/bg2361sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034628/bg2361Isup2.hkl

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

C11H15N5O	Z = 4
Mr = 233.28	F(000) = 496
Triclinic, P1	Dx = 1.274 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2565 (8) Å	Cell parameters from 1894 reflections
b = 11.2229 (11) Å	θ = 2.7–24.3°
c = 13.4021 (13) Å	µ = 0.09 mm−1
α = 78.421 (1)°	T = 298 K
β = 89.551 (2)°	Block, colourless
γ = 88.483 (1)°	0.48 × 0.47 × 0.14 mm
V = 1216.2 (2) Å3

Bruker APEXII CCD area-detector diffractometer	4208 independent reflections
Radiation source: fine-focus sealed tube	2538 reflections with I > 2σ(I)
graphite	Rint = 0.030
phi and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.96, Tmax = 0.99	k = −13→12
6288 measured reflections	l = −15→15

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0626P)2 + 0.3212P] where P = (Fo2 + 2Fc2)/3
4208 reflections	(Δ/σ)max < 0.001
313 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.22 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
N1	0.2572 (3)	0.8076 (2)	0.01198 (17)	0.0416 (6)
N2	0.3297 (3)	0.9315 (2)	0.11520 (19)	0.0483 (6)
N3	−0.0300 (3)	0.7899 (2)	0.0569 (2)	0.0498 (7)
N4	−0.1029 (3)	0.9008 (2)	0.18776 (19)	0.0480 (7)
N5	0.0816 (3)	1.0018 (2)	0.26608 (19)	0.0529 (7)
H5A	0.0059	1.0165	0.3067	0.063*
H5B	0.1776	1.0275	0.2720	0.063*
N6	0.7455 (3)	0.2103 (2)	0.49198 (17)	0.0410 (6)
N7	0.8180 (3)	0.0572 (2)	0.41366 (18)	0.0437 (6)
N8	0.4600 (3)	0.2330 (2)	0.44317 (19)	0.0493 (7)
N9	0.3889 (3)	0.0939 (2)	0.33544 (19)	0.0471 (6)
N10	0.5742 (3)	−0.0341 (2)	0.2781 (2)	0.0542 (7)
H10A	0.5002	−0.0547	0.2405	0.065*
H10B	0.6704	−0.0653	0.2779	0.065*
O1	0.4200 (4)	0.5832 (2)	0.1274 (2)	0.0890 (9)
O2	0.9215 (3)	0.3952 (2)	0.34758 (19)	0.0747 (7)
C1	0.3770 (4)	0.8703 (3)	0.0464 (2)	0.0477 (8)
H1	0.4832	0.8695	0.0229	0.057*
C2	0.1666 (3)	0.9074 (2)	0.1277 (2)	0.0378 (7)
C3	0.1211 (3)	0.8310 (2)	0.0644 (2)	0.0386 (7)
C4	−0.1302 (4)	0.8313 (3)	0.1201 (3)	0.0514 (8)
H4	−0.2371	0.8082	0.1169	0.062*
C5	0.0503 (3)	0.9394 (3)	0.1940 (2)	0.0420 (7)
C6	0.2743 (4)	0.7212 (3)	−0.0589 (2)	0.0478 (8)
C7	0.2204 (4)	0.5963 (3)	−0.0013 (2)	0.0559 (9)
H7A	0.1040	0.6009	0.0083	0.067*
H7B	0.2414	0.5381	−0.0447	0.067*
C8	0.2954 (5)	0.5463 (3)	0.1002 (3)	0.0608 (9)
C9	0.2085 (5)	0.4448 (5)	0.1656 (4)	0.1136 (18)
H9A	0.2738	0.4109	0.2239	0.170*
H9B	0.1882	0.3830	0.1274	0.170*
H9C	0.1075	0.4751	0.1878	0.170*
C10	0.1629 (4)	0.7668 (3)	−0.1489 (2)	0.0661 (10)
H10C	0.0531	0.7699	−0.1253	0.099*
H10D	0.1713	0.7126	−0.1959	0.099*
H10E	0.1939	0.8467	−0.1826	0.099*
C11	0.4479 (4)	0.7178 (3)	−0.0957 (3)	0.0684 (10)
H11A	0.4784	0.7983	−0.1283	0.103*
H11B	0.4575	0.6646	−0.1434	0.103*
H11C	0.5179	0.6885	−0.0387	0.103*
C12	0.8644 (4)	0.1328 (3)	0.4701 (2)	0.0452 (7)
H12	0.9701	0.1334	0.4934	0.054*
C13	0.6556 (3)	0.0876 (2)	0.3974 (2)	0.0371 (7)
C14	0.6081 (3)	0.1810 (2)	0.4449 (2)	0.0383 (7)
C15	0.3592 (4)	0.1818 (3)	0.3882 (2)	0.0510 (8)
H15	0.2527	0.2113	0.3860	0.061*
C16	0.5397 (3)	0.0464 (3)	0.3364 (2)	0.0403 (7)
C17	0.7629 (4)	0.3162 (3)	0.5422 (2)	0.0485 (8)
C18	0.7157 (4)	0.4315 (3)	0.4650 (2)	0.0544 (9)
H18A	0.6011	0.4286	0.4506	0.065*
H18B	0.7303	0.5007	0.4970	0.065*
C19	0.8052 (4)	0.4549 (3)	0.3652 (3)	0.0539 (8)
C20	0.7440 (5)	0.5588 (4)	0.2860 (3)	0.0932 (14)
H20A	0.8196	0.5739	0.2304	0.140*
H20B	0.7319	0.6301	0.3150	0.140*
H20C	0.6409	0.5393	0.2616	0.140*
C21	0.6479 (5)	0.3011 (3)	0.6328 (3)	0.0689 (10)
H21A	0.5399	0.2908	0.6106	0.103*
H21B	0.6503	0.3722	0.6624	0.103*
H21C	0.6810	0.2309	0.6826	0.103*
C22	0.9356 (4)	0.3201 (3)	0.5801 (3)	0.0658 (10)
H22A	0.9617	0.2457	0.6271	0.099*
H22B	0.9449	0.3875	0.6137	0.099*
H22C	1.0091	0.3296	0.5234	0.099*

	U11	U22	U33	U12	U13	U23
N1	0.0432 (15)	0.0402 (14)	0.0416 (14)	−0.0020 (11)	−0.0024 (11)	−0.0081 (12)
N2	0.0399 (15)	0.0545 (16)	0.0540 (16)	−0.0090 (12)	0.0030 (12)	−0.0182 (14)
N3	0.0428 (15)	0.0531 (16)	0.0546 (16)	−0.0070 (13)	−0.0073 (13)	−0.0124 (13)
N4	0.0373 (15)	0.0555 (16)	0.0543 (16)	−0.0047 (12)	−0.0040 (12)	−0.0179 (14)
N5	0.0375 (14)	0.0680 (18)	0.0615 (18)	−0.0062 (12)	0.0024 (12)	−0.0322 (15)
N6	0.0405 (14)	0.0402 (14)	0.0443 (15)	−0.0105 (11)	−0.0026 (11)	−0.0117 (12)
N7	0.0405 (15)	0.0447 (15)	0.0468 (15)	−0.0047 (11)	−0.0044 (11)	−0.0107 (12)
N8	0.0414 (15)	0.0525 (16)	0.0564 (17)	−0.0053 (12)	0.0008 (12)	−0.0162 (13)
N9	0.0362 (14)	0.0584 (17)	0.0485 (15)	−0.0103 (12)	0.0028 (11)	−0.0141 (13)
N10	0.0401 (15)	0.0626 (17)	0.0674 (18)	−0.0084 (13)	−0.0063 (13)	−0.0296 (15)
O1	0.105 (2)	0.0779 (19)	0.0757 (19)	−0.0019 (17)	−0.0336 (17)	0.0054 (15)
O2	0.0770 (18)	0.0712 (17)	0.0722 (17)	−0.0083 (15)	0.0210 (14)	−0.0060 (14)
C1	0.0407 (18)	0.0519 (19)	0.0516 (19)	−0.0047 (15)	0.0015 (15)	−0.0127 (16)
C2	0.0346 (16)	0.0395 (16)	0.0397 (16)	−0.0041 (13)	−0.0008 (13)	−0.0086 (14)
C3	0.0356 (17)	0.0368 (16)	0.0401 (17)	−0.0022 (13)	−0.0043 (13)	0.0003 (13)
C4	0.0369 (18)	0.057 (2)	0.061 (2)	−0.0090 (15)	−0.0038 (16)	−0.0118 (18)
C5	0.0388 (17)	0.0430 (17)	0.0443 (18)	−0.0021 (13)	−0.0043 (14)	−0.0090 (15)
C6	0.066 (2)	0.0417 (18)	0.0365 (17)	0.0014 (15)	−0.0023 (15)	−0.0108 (14)
C7	0.072 (2)	0.0430 (18)	0.055 (2)	−0.0013 (16)	−0.0081 (17)	−0.0142 (16)
C8	0.071 (2)	0.050 (2)	0.057 (2)	0.0128 (19)	0.001 (2)	−0.0020 (18)
C9	0.082 (3)	0.136 (4)	0.094 (3)	0.003 (3)	0.021 (3)	0.046 (3)
C10	0.090 (3)	0.064 (2)	0.044 (2)	0.001 (2)	−0.0139 (18)	−0.0098 (17)
C11	0.076 (3)	0.072 (2)	0.061 (2)	0.007 (2)	0.0088 (19)	−0.025 (2)
C12	0.0390 (17)	0.0495 (18)	0.0470 (18)	−0.0084 (14)	−0.0061 (14)	−0.0085 (15)
C13	0.0333 (16)	0.0371 (16)	0.0392 (16)	−0.0083 (12)	0.0007 (12)	−0.0023 (13)
C14	0.0366 (17)	0.0387 (16)	0.0385 (16)	−0.0105 (13)	0.0033 (13)	−0.0043 (13)
C15	0.0388 (18)	0.061 (2)	0.053 (2)	−0.0028 (15)	0.0017 (15)	−0.0096 (17)
C16	0.0384 (17)	0.0437 (17)	0.0392 (17)	−0.0127 (14)	0.0050 (13)	−0.0078 (14)
C17	0.055 (2)	0.0488 (19)	0.0442 (18)	−0.0177 (15)	0.0027 (15)	−0.0142 (15)
C18	0.060 (2)	0.0439 (19)	0.063 (2)	−0.0120 (16)	0.0047 (17)	−0.0175 (17)
C19	0.054 (2)	0.051 (2)	0.056 (2)	−0.0205 (17)	−0.0019 (17)	−0.0063 (17)
C20	0.086 (3)	0.108 (3)	0.073 (3)	−0.002 (3)	−0.013 (2)	0.012 (3)
C21	0.083 (3)	0.074 (2)	0.055 (2)	−0.020 (2)	0.0121 (19)	−0.0231 (19)
C22	0.071 (2)	0.065 (2)	0.066 (2)	−0.0249 (19)	−0.0131 (19)	−0.0202 (19)

N1—C1	1.364 (3)	C7—C8	1.495 (5)
N1—C3	1.368 (3)	C7—H7A	0.9700
N1—C6	1.491 (3)	C7—H7B	0.9700
N2—C1	1.307 (4)	C8—C9	1.488 (5)
N2—C2	1.383 (3)	C9—H9A	0.9600
N3—C4	1.320 (4)	C9—H9B	0.9600
N3—C3	1.353 (3)	C9—H9C	0.9600
N4—C4	1.334 (4)	C10—H10C	0.9600
N4—C5	1.356 (3)	C10—H10D	0.9600
N5—C5	1.333 (3)	C10—H10E	0.9600
N5—H5A	0.8600	C11—H11A	0.9600
N5—H5B	0.8600	C11—H11B	0.9600
N6—C12	1.364 (4)	C11—H11C	0.9600
N6—C14	1.382 (3)	C12—H12	0.9300
N6—C17	1.489 (3)	C13—C14	1.378 (4)
N7—C12	1.311 (3)	C13—C16	1.409 (4)
N7—C13	1.383 (3)	C15—H15	0.9300
N8—C15	1.331 (4)	C17—C21	1.520 (4)
N8—C14	1.339 (3)	C17—C22	1.522 (4)
N9—C15	1.340 (4)	C17—C18	1.530 (4)
N9—C16	1.341 (3)	C18—C19	1.502 (5)
N10—C16	1.332 (3)	C18—H18A	0.9700
N10—H10A	0.8600	C18—H18B	0.9700
N10—H10B	0.8600	C19—C20	1.491 (5)
O1—C8	1.205 (4)	C20—H20A	0.9600
O2—C19	1.205 (4)	C20—H20B	0.9600
C1—H1	0.9300	C20—H20C	0.9600
C2—C3	1.381 (4)	C21—H21A	0.9600
C2—C5	1.392 (4)	C21—H21B	0.9600
C4—H4	0.9300	C21—H21C	0.9600
C6—C11	1.514 (5)	C22—H22A	0.9600
C6—C10	1.519 (4)	C22—H22B	0.9600
C6—C7	1.534 (4)	C22—H22C	0.9600
C1—N1—C3	105.2 (2)	C6—C10—H10E	109.5
C1—N1—C6	127.4 (2)	H10C—C10—H10E	109.5
C3—N1—C6	127.1 (2)	H10D—C10—H10E	109.5
C1—N2—C2	104.0 (2)	C6—C11—H11A	109.5
C4—N3—C3	110.7 (2)	C6—C11—H11B	109.5
C4—N4—C5	117.3 (3)	H11A—C11—H11B	109.5
C5—N5—H5A	120.0	C6—C11—H11C	109.5
C5—N5—H5B	120.0	H11A—C11—H11C	109.5
H5A—N5—H5B	120.0	H11B—C11—H11C	109.5
C12—N6—C14	105.3 (2)	N7—C12—N6	114.8 (2)
C12—N6—C17	127.9 (2)	N7—C12—H12	122.6
C14—N6—C17	126.3 (2)	N6—C12—H12	122.6
C12—N7—C13	103.0 (2)	C14—C13—N7	111.5 (2)
C15—N8—C14	110.7 (2)	C14—C13—C16	117.1 (3)
C15—N9—C16	118.3 (2)	N7—C13—C16	131.2 (3)
C16—N10—H10A	120.0	N8—C14—C13	126.6 (3)
C16—N10—H10B	120.0	N8—C14—N6	127.9 (2)
H10A—N10—H10B	120.0	C13—C14—N6	105.5 (2)
N2—C1—N1	114.3 (3)	N8—C15—N9	129.4 (3)
N2—C1—H1	122.9	N8—C15—H15	115.3
N1—C1—H1	122.9	N9—C15—H15	115.3
C3—C2—N2	110.0 (2)	N10—C16—N9	119.0 (2)
C3—C2—C5	117.7 (3)	N10—C16—C13	123.3 (3)
N2—C2—C5	132.2 (2)	N9—C16—C13	117.7 (2)
N3—C3—N1	127.9 (3)	N6—C17—C21	108.4 (2)
N3—C3—C2	125.6 (3)	N6—C17—C22	110.1 (3)
N1—C3—C2	106.5 (2)	C21—C17—C22	108.8 (3)
N3—C4—N4	130.4 (3)	N6—C17—C18	108.0 (2)
N3—C4—H4	114.8	C21—C17—C18	109.6 (3)
N4—C4—H4	114.8	C22—C17—C18	111.8 (3)
N5—C5—N4	117.8 (3)	C19—C18—C17	117.3 (3)
N5—C5—C2	123.9 (3)	C19—C18—H18A	108.0
N4—C5—C2	118.2 (2)	C17—C18—H18A	108.0
N1—C6—C11	109.7 (2)	C19—C18—H18B	108.0
N1—C6—C10	107.7 (2)	C17—C18—H18B	108.0
C11—C6—C10	109.7 (3)	H18A—C18—H18B	107.2
N1—C6—C7	107.6 (2)	O2—C19—C20	119.9 (3)
C11—C6—C7	112.1 (3)	O2—C19—C18	123.5 (3)
C10—C6—C7	109.9 (3)	C20—C19—C18	116.6 (3)
C8—C7—C6	117.9 (3)	C19—C20—H20A	109.5
C8—C7—H7A	107.8	C19—C20—H20B	109.5
C6—C7—H7A	107.8	H20A—C20—H20B	109.5
C8—C7—H7B	107.8	C19—C20—H20C	109.5
C6—C7—H7B	107.8	H20A—C20—H20C	109.5
H7A—C7—H7B	107.2	H20B—C20—H20C	109.5
O1—C8—C9	121.4 (4)	C17—C21—H21A	109.5
O1—C8—C7	122.9 (3)	C17—C21—H21B	109.5
C9—C8—C7	115.7 (4)	H21A—C21—H21B	109.5
C8—C9—H9A	109.5	C17—C21—H21C	109.5
C8—C9—H9B	109.5	H21A—C21—H21C	109.5
H9A—C9—H9B	109.5	H21B—C21—H21C	109.5
C8—C9—H9C	109.5	C17—C22—H22A	109.5
H9A—C9—H9C	109.5	C17—C22—H22B	109.5
H9B—C9—H9C	109.5	H22A—C22—H22B	109.5
C6—C10—H10C	109.5	C17—C22—H22C	109.5
C6—C10—H10D	109.5	H22A—C22—H22C	109.5
H10C—C10—H10D	109.5	H22B—C22—H22C	109.5
C2—N2—C1—N1	0.2 (3)	C13—N7—C12—N6	−0.1 (3)
C3—N1—C1—N2	−0.3 (3)	C14—N6—C12—N7	0.3 (3)
C6—N1—C1—N2	−174.2 (3)	C17—N6—C12—N7	−171.4 (3)
C1—N2—C2—C3	0.0 (3)	C12—N7—C13—C14	−0.1 (3)
C1—N2—C2—C5	175.5 (3)	C12—N7—C13—C16	174.6 (3)
C4—N3—C3—N1	179.6 (3)	C15—N8—C14—C13	0.1 (4)
C4—N3—C3—C2	−1.0 (4)	C15—N8—C14—N6	178.7 (3)
C1—N1—C3—N3	179.7 (3)	N7—C13—C14—N8	179.1 (3)
C6—N1—C3—N3	−6.4 (5)	C16—C13—C14—N8	3.6 (4)
C1—N1—C3—C2	0.2 (3)	N7—C13—C14—N6	0.2 (3)
C6—N1—C3—C2	174.2 (2)	C16—C13—C14—N6	−175.2 (2)
N2—C2—C3—N3	−179.6 (3)	C12—N6—C14—N8	−179.1 (3)
C5—C2—C3—N3	4.2 (4)	C17—N6—C14—N8	−7.2 (5)
N2—C2—C3—N1	−0.1 (3)	C12—N6—C14—C13	−0.3 (3)
C5—C2—C3—N1	−176.4 (2)	C17—N6—C14—C13	171.6 (3)
C3—N3—C4—N4	−1.9 (5)	C14—N8—C15—N9	−2.5 (5)
C5—N4—C4—N3	1.4 (5)	C16—N9—C15—N8	0.8 (5)
C4—N4—C5—N5	−175.5 (3)	C15—N9—C16—N10	−174.7 (3)
C4—N4—C5—C2	2.1 (4)	C15—N9—C16—C13	3.2 (4)
C3—C2—C5—N5	172.9 (3)	C14—C13—C16—N10	172.7 (3)
N2—C2—C5—N5	−2.3 (5)	N7—C13—C16—N10	−1.7 (5)
C3—C2—C5—N4	−4.5 (4)	C14—C13—C16—N9	−5.2 (4)
N2—C2—C5—N4	−179.8 (3)	N7—C13—C16—N9	−179.6 (3)
C1—N1—C6—C11	−4.0 (4)	C12—N6—C17—C21	−126.0 (3)
C3—N1—C6—C11	−176.7 (3)	C14—N6—C17—C21	64.0 (4)
C1—N1—C6—C10	−123.4 (3)	C12—N6—C17—C22	−7.0 (4)
C3—N1—C6—C10	64.0 (4)	C14—N6—C17—C22	−177.1 (3)
C1—N1—C6—C7	118.2 (3)	C12—N6—C17—C18	115.3 (3)
C3—N1—C6—C7	−54.5 (4)	C14—N6—C17—C18	−54.7 (4)
N1—C6—C7—C8	−52.1 (4)	N6—C17—C18—C19	−56.0 (3)
C11—C6—C7—C8	68.6 (4)	C21—C17—C18—C19	−173.9 (3)
C10—C6—C7—C8	−169.1 (3)	C22—C17—C18—C19	65.3 (3)
C6—C7—C8—O1	−18.3 (5)	C17—C18—C19—O2	−8.0 (5)
C6—C7—C8—C9	163.2 (3)	C17—C18—C19—C20	172.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10B···N4i	0.86	2.28	3.051 (3)	149
N10—H10A···N2ii	0.86	2.23	3.072 (3)	166
N5—H5B···N9iii	0.86	2.16	2.988 (3)	161
N5—H5A···N7iv	0.86	2.20	3.064 (3)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10B⋯N4i	0.86	2.28	3.051 (3)	149
N10—H10A⋯N2ii	0.86	2.23	3.072 (3)	166
N5—H5B⋯N9iii	0.86	2.16	2.988 (3)	161
N5—H5A⋯N7iv	0.86	2.20	3.064 (3)	178

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .