9-(Cyclo­hexyl­methyl)-6-(di­methyl­amino)-9H-purine

The purine fragment of the title compound, C₁₄H₂₁N₅, is planar and the di­methyl­amino group is almost coplanar with it. The cyclo­hexyl fragment (in a chair conformation) is disordered between two positions. C—H...N hydrogen bonds determine the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.057
• wR factor = 0.124
• Data-to-parameter ratio = 15.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_301  Alert C Main Residue Disorder ........................      24.00 Perc.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

The title compound, (I), was synthesized as part of a series of potential anticonvulsants. Its activity against maximum electroshock-induced seizures was evaluated as moderate. An effective dose, ED₅₀, is 25 mg kg^-1 for an ip admission in rats (Kelley et al., 1988). The compound was also tested for an activity against apomorphine-induced aggresive behavior (Kelley et al., 1997), but the results were negative.

Fig. 1 shows a perspective view of the molecule. The purine fragment is almost perfectly planar; the maximum deviation from the least-squares plane through the nine ring atoms is 0.025 (3) Å. The dihedral angle between this plane and the dimethylamino plane is small [3.2 (3)°] and indicates significant conjugation. The bond lengths and angles pattern is quite typical, including the large value of the N1—C2—N3 angle [129.9 (2)°; for 244 similar fragments in CSD (Allen & Kennard, 1993), the mean value is 129 (1)°].

The cyclohexyl fragment is disordered, and the site-occupation factors for two alternative positions (hereinafter referred to as A and B) are 0.841 (3) and 0.159 (3). In both positions, the cyclohexane ring adopts a chair conformation. This conformation is close to an ideal one for molecule A; the largest value of the asymmetry parameter (Duax & Norton, 1976) is 1.10°. A view of disordered fragment is shown in Fig. 2, the dihedral angle between least-squares planes of `seats' of both chairs is 64.3 (5)°.

The molecules are connected into infinite chains along the [010] direction by C—H···N hydrogen bonds. This interaction determines the crystal packing, and therefore can not be treated as an artifact. The linearity of this bond as well as short H···N and C···N distances allow to classify this hydrogen bond as a relatively strong one (cf. Taylor & Kennard, 1982; Reddy et al., 1993; Kubicki, Borowiak, Suwiński & Wagner, 2001). Also, the results of charge–density studies of 1-phenyl-4-nitroimidazole suggest that the C—H···N hydrogen bond of similar geometry has topological features comparable with well defined C—H···O hydrogen bonds (Kubicki, Borowiak, Dutkiewicz et al., 2001).

There are three potential hydrogen-bond acceptors (N1, N3 and N7), but the in-plane access to N1 and N7 is partially hindered by the C61 and C62 methyl groups. In the crystal structure, there are alternate hydrophobic (dimethylamine and cyclohexylmethyl) and hydrophilic (purine) layers (Fig. 3).

S2. Experimental

Colourless crystals of (I) were grown from ethanol by slow evaporation.

S3. Refinement

The sum of site-occupancy factors for the disordered fragment was constrained to unity. The C atoms in the less occupied cyclohexane ring were refined isotropically and the U_iso value of C94 was fixed; bond lengths and angles in this fragment were constrained to typical values.

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: ENPROC (Rettig, 1978); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation (Siemens, 1989).

Figures

	Fig. 1. A perspective view of the molecule with the numbering scheme (Siemens, 1989). Displacement ellipsoids are drawn at the 33% probability level and H atoms are depicted as spheres of arbitrary radii. Only the molecule of higher occupancy is shown.
	Fig. 2. A comparison of disordered cyclohexyl fragments (Siemens, 1989). The bonds in the less occupied part are shown as dashed lines. H atoms have been omitted for clarity.
	Fig. 3. The crystal-packing scheme (Siemens, 1989). Hydrogen bonds are drawn as dashed lines and the view is approximately along the [001] direction.

9-(Cyclohexylmethyl)-6-(dimethylamino)-9H-purine

Crystal data

C14H21N5	F(000) = 560
Mr = 259.36	Dx = 1.178 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 5.7702 (5) Å	Cell parameters from 25 reflections
b = 11.321 (1) Å	θ = 11–37°
c = 22.390 (1) Å	µ = 0.59 mm^−1
β = 91.47 (1)°	T = 293 K
V = 1462.1 (2) Å^3	Block, colourless
Z = 4	0.25 × 0.2 × 0.1 mm

Data collection

CAD-4F four-circle diffractometer	Rint = 0.043
Radiation source: fine-focus sealed tube	θmax = 74.8°, θmin = 4.0°
Ni-filter monochromator	h = 0→7
ω/2θ scans	k = −14→14
6589 measured reflections	l = −28→28
2992 independent reflections	2 standard reflections every 33 min
2162 reflections with I > 2σ(I)	intensity decay: 3%

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)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.01P)^2 + 0.5P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2992 reflections	Δρmax = 0.24 e Å^−3
197 parameters	Δρmin = −0.17 e Å^−3
12 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: 0.0173 (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	Occ. (<1)
N1	0.1431 (3)	0.66126 (15)	0.16416 (7)	0.0711 (5)
C2	0.2735 (4)	0.60225 (18)	0.20362 (10)	0.0728 (6)
H2	0.2292	0.5243	0.2098	0.087*
N3	0.4571 (3)	0.63731 (14)	0.23547 (7)	0.0680 (5)
C4	0.5077 (3)	0.75039 (16)	0.22279 (8)	0.0573 (4)
C5	0.3897 (3)	0.82457 (16)	0.18354 (8)	0.0590 (5)
C6	0.1953 (3)	0.77528 (18)	0.15283 (8)	0.0638 (5)
N6	0.0565 (3)	0.83347 (17)	0.11345 (8)	0.0817 (5)
C61	−0.1364 (4)	0.7738 (3)	0.08395 (11)	0.1008 (8)
H61A	−0.2164	0.8280	0.0577	0.141*
H61B	−0.2411	0.7454	0.1133	0.141*
H61C	−0.0798	0.7084	0.0613	0.141*
C62	0.0878 (5)	0.9563 (2)	0.09911 (11)	0.1073 (9)
H62A	−0.0292	0.9804	0.0704	0.150*
H62B	0.2383	0.9676	0.0827	0.150*
H62C	0.0750	1.0030	0.1347	0.150*
N7	0.5010 (3)	0.93380 (14)	0.18187 (7)	0.0717 (5)
C8	0.6753 (4)	0.92211 (18)	0.21938 (9)	0.0713 (6)
H8	0.7805	0.9826	0.2275	0.086*
N9	0.6909 (3)	0.81419 (14)	0.24574 (7)	0.0625 (4)
C9	0.8640 (3)	0.77403 (19)	0.28973 (9)	0.0713 (6)
H9A	1.0009	0.8232	0.2867	0.086*	0.843 (3)
H9B	0.9083	0.6938	0.2799	0.086*	0.843 (3)
H9C	1.0183	0.7897	0.2755	0.086*	0.157 (3)
H9D	0.8489	0.6896	0.2958	0.086*	0.157 (3)
C91A	0.7850 (4)	0.7771 (2)	0.35435 (10)	0.0629 (6)	0.843 (3)
H91A	0.6377	0.7343	0.3561	0.075*	0.843 (3)
C92A	0.7449 (6)	0.9017 (2)	0.37642 (11)	0.0886 (10)	0.843 (3)
H92A	0.6244	0.9383	0.3517	0.106*	0.843 (3)
H92B	0.8859	0.9472	0.3719	0.106*	0.843 (3)
C93A	0.6745 (8)	0.9063 (3)	0.44153 (13)	0.1041 (11)	0.843 (3)
H93A	0.6612	0.9881	0.4540	0.125*	0.843 (3)
H93B	0.5242	0.8692	0.4455	0.125*	0.843 (3)
C94A	0.8493 (7)	0.8443 (3)	0.48122 (13)	0.1027 (12)	0.843 (3)
H94A	0.7957	0.8438	0.5219	0.123*	0.843 (3)
H94B	0.9953	0.8868	0.4808	0.123*	0.843 (3)
C95A	0.8862 (7)	0.7190 (3)	0.46047 (14)	0.1185 (14)	0.843 (3)
H95A	0.7436	0.6746	0.4645	0.142*	0.843 (3)
H95B	1.0048	0.6819	0.4856	0.142*	0.843 (3)
C96A	0.9590 (6)	0.7154 (3)	0.39590 (13)	0.0969 (11)	0.843 (3)
H96A	0.9750	0.6338	0.3835	0.116*	0.843 (3)
H96B	1.1091	0.7532	0.3927	0.116*	0.843 (3)
C91B	0.8324 (18)	0.8399 (14)	0.3453 (4)	0.065 (4)*	0.157 (3)
H91B	0.8395	0.9247	0.3370	0.078*	0.157 (3)
C92B	0.6039 (17)	0.8115 (14)	0.3726 (5)	0.085 (4)*	0.157 (3)
H92C	0.5818	0.7266	0.3722	0.102*	0.157 (3)
H92D	0.4804	0.8465	0.3483	0.102*	0.157 (3)
C93B	0.586 (2)	0.8558 (19)	0.4360 (6)	0.115 (9)*	0.157 (3)
H93C	0.4459	0.8252	0.4532	0.137*	0.157 (3)
H93D	0.5765	0.9413	0.4357	0.137*	0.157 (3)
C94B	0.796 (3)	0.818 (2)	0.4746 (5)	0.120*	0.157 (3)
H94C	0.8008	0.7321	0.4773	0.144*	0.157 (3)
H94D	0.7825	0.8491	0.5147	0.144*	0.157 (3)
C95B	1.019 (2)	0.8635 (16)	0.4467 (6)	0.120 (7)*	0.157 (3)
H95C	1.1523	0.8436	0.4720	0.144*	0.157 (3)
H95D	1.0124	0.9487	0.4425	0.144*	0.157 (3)
C96B	1.0406 (17)	0.8049 (14)	0.3848 (5)	0.086 (4)*	0.157 (3)
H96C	1.1826	0.8305	0.3665	0.103*	0.157 (3)
H96D	1.0461	0.7197	0.3892	0.103*	0.157 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0694 (10)	0.0694 (11)	0.0742 (11)	−0.0018 (9)	−0.0039 (8)	−0.0095 (8)
C2	0.0715 (13)	0.0604 (12)	0.0863 (14)	−0.0050 (10)	−0.0014 (11)	−0.0020 (10)
N3	0.0696 (10)	0.0574 (9)	0.0769 (10)	−0.0002 (8)	−0.0031 (8)	0.0029 (8)
C4	0.0611 (10)	0.0560 (10)	0.0548 (10)	0.0018 (8)	0.0029 (8)	−0.0060 (8)
C5	0.0679 (11)	0.0565 (10)	0.0527 (9)	0.0046 (9)	0.0035 (8)	−0.0043 (8)
C6	0.0666 (11)	0.0703 (12)	0.0543 (10)	0.0087 (10)	0.0006 (9)	−0.0074 (9)
N6	0.0879 (13)	0.0860 (13)	0.0700 (10)	0.0132 (10)	−0.0181 (9)	−0.0046 (9)
C61	0.0844 (16)	0.136 (2)	0.0814 (15)	0.0163 (16)	−0.0202 (13)	−0.0213 (15)
C62	0.128 (2)	0.102 (2)	0.0907 (17)	0.0200 (17)	−0.0180 (16)	0.0232 (15)
N7	0.0905 (12)	0.0561 (9)	0.0683 (10)	−0.0017 (9)	0.0005 (9)	−0.0006 (8)
C8	0.0824 (14)	0.0597 (11)	0.0717 (12)	−0.0095 (10)	0.0011 (11)	−0.0081 (10)
N9	0.0659 (10)	0.0602 (9)	0.0613 (9)	−0.0012 (8)	−0.0014 (7)	−0.0071 (7)
C9	0.0615 (11)	0.0750 (13)	0.0769 (13)	0.0077 (10)	−0.0088 (10)	−0.0177 (10)
C91A	0.0641 (14)	0.0585 (14)	0.0652 (14)	−0.0007 (11)	−0.0127 (11)	−0.0012 (11)
C92A	0.119 (2)	0.0758 (18)	0.0714 (16)	0.0312 (17)	0.0126 (15)	−0.0003 (13)
C93A	0.135 (3)	0.104 (3)	0.0747 (19)	0.017 (3)	0.0218 (19)	−0.0086 (17)
C94A	0.132 (3)	0.111 (3)	0.0644 (16)	−0.032 (2)	−0.0079 (18)	−0.0121 (16)
C95A	0.171 (4)	0.096 (2)	0.085 (2)	−0.005 (2)	−0.064 (2)	0.0058 (17)
C96A	0.115 (2)	0.0776 (19)	0.096 (2)	0.0256 (17)	−0.0452 (18)	−0.0200 (15)

Geometric parameters (Å, º)

N1—C2	1.326 (2)	C92A—C93A	1.524 (4)
N1—C6	1.351 (2)	C92A—H92A	0.9700
C2—N3	1.323 (2)	C92A—H92B	0.9700
C2—H2	0.9300	C93A—C94A	1.501 (5)
N3—C4	1.345 (2)	C93A—H93A	0.9700
C4—N9	1.370 (2)	C93A—H93B	0.9700
C4—C5	1.382 (2)	C94A—C95A	1.510 (5)
C5—N7	1.394 (2)	C94A—H94A	0.9700
C5—C6	1.416 (3)	C94A—H94B	0.9700
C6—N6	1.348 (2)	C95A—C96A	1.516 (5)
N6—C62	1.440 (3)	C95A—H95A	0.9700
N6—C61	1.447 (3)	C95A—H95B	0.9700
C61—H61A	0.9600	C96A—H96A	0.9700
C61—H61B	0.9600	C96A—H96B	0.9700
C61—H61C	0.9600	C91B—C92B	1.501 (9)
C62—H62A	0.9600	C91B—C96B	1.525 (9)
C62—H62B	0.9600	C91B—H91B	0.9800
C62—H62C	0.9600	C92B—C93B	1.511 (9)
N7—C8	1.300 (3)	C92B—H92C	0.9700
C8—N9	1.359 (2)	C92B—H92D	0.9700
C8—H8	0.9300	C93B—C94B	1.53 (1)
N9—C9	1.458 (2)	C93B—H93C	0.9700
C9—C91B	1.47 (1)	C93B—H93D	0.9700
C9—C91A	1.529 (3)	C94B—C95B	1.54 (1)
C9—H9A	0.9701	C94B—H94C	0.9700
C9—H9B	0.9700	C94B—H94D	0.9700
C9—H9C	0.9700	C95B—C96B	1.544 (9)
C9—H9D	0.9700	C95B—H95C	0.9700
C91A—C92A	1.514 (3)	C95B—H95D	0.9700
C91A—C96A	1.521 (3)	C96B—H96C	0.9700
C91A—H91A	0.9800	C96B—H96D	0.9700
C2—N1—C6	118.7 (2)	C94A—C93A—H93A	109.4
N3—C2—N1	129.9 (2)	C92A—C93A—H93A	109.4
N3—C2—H2	115.1	C94A—C93A—H93B	109.4
N1—C2—H2	115.1	C92A—C93A—H93B	109.4
C2—N3—C4	110.3 (2)	H93A—C93A—H93B	108.0
N3—C4—N9	126.3 (2)	C93A—C94A—C95A	110.8 (3)
N3—C4—C5	127.4 (2)	C93A—C94A—H94A	109.5
N9—C4—C5	106.3 (2)	C95A—C94A—H94A	109.5
C4—C5—N7	109.7 (2)	C93A—C94A—H94B	109.5
C4—C5—C6	116.1 (2)	C95A—C94A—H94B	109.5
N7—C5—C6	134.1 (2)	H94A—C94A—H94B	108.1
N6—C6—N1	117.3 (2)	C94A—C95A—C96A	111.3 (3)
N6—C6—C5	125.1 (2)	C94A—C95A—H95A	109.4
N1—C6—C5	117.6 (2)	C96A—C95A—H95A	109.4
C6—N6—C62	122.8 (2)	C94A—C95A—H95B	109.4
C6—N6—C61	120.5 (2)	C96A—C95A—H95B	109.4
C62—N6—C61	116.6 (2)	H95A—C95A—H95B	108.0
N6—C61—H61A	109.5	C95A—C96A—C91A	112.1 (3)
N6—C61—H61B	109.5	C95A—C96A—H96A	109.2
H61A—C61—H61B	109.5	C91A—C96A—H96A	109.2
N6—C61—H61C	109.5	C95A—C96A—H96B	109.2
H61A—C61—H61C	109.5	C91A—C96A—H96B	109.2
H61B—C61—H61C	109.5	H96A—C96A—H96B	107.9
N6—C62—H62A	109.5	C9—C91B—C92B	111 (1)
N6—C62—H62B	109.5	C9—C91B—C96B	104.3 (8)
H62A—C62—H62B	109.5	C92B—C91B—C96B	113.3 (8)
N6—C62—H62C	109.5	C9—C91B—H91B	109.2
H62A—C62—H62C	109.5	C92B—C91B—H91B	109.2
H62B—C62—H62C	109.5	C96B—C91B—H91B	109.2
C8—N7—C5	104.0 (2)	C91B—C92B—C93B	113.0 (8)
N7—C8—N9	114.4 (2)	C91B—C92B—H92C	109.0
N7—C8—H8	122.8	C93B—C92B—H92C	109.0
N9—C8—H8	122.8	C91B—C92B—H92D	109.0
C8—N9—C4	105.6 (2)	C93B—C92B—H92D	109.0
C8—N9—C9	127.6 (2)	H92C—C92B—H92D	107.8
C4—N9—C9	126.7 (2)	C92B—C93B—C94B	111.5 (9)
N9—C9—C91B	108.5 (5)	C92B—C93B—H93C	109.3
N9—C9—C91A	114.6 (2)	C94B—C93B—H93C	109.3
N9—C9—H9A	108.6	C92B—C93B—H93D	109.3
C91A—C9—H9A	108.5	C94B—C93B—H93D	109.3
N9—C9—H9B	108.6	H93C—C93B—H93D	108.0
C91A—C9—H9B	108.8	C93B—C94B—C95B	109.4 (9)
H9A—C9—H9B	107.6	C93B—C94B—H94C	109.8
N9—C9—H9C	109.8	C95B—C94B—H94C	109.8
C91B—C9—H9C	108.8	C93B—C94B—H94D	109.8
N9—C9—H9D	109.9	C95B—C94B—H94D	109.8
H9C—C9—H9D	108.3	H94C—C94B—H94D	108.2
C92A—C91A—C96A	109.4 (2)	C94B—C95B—C96B	107.9 (8)
C92A—C91A—C9	112.5 (2)	C94B—C95B—H95C	110.1
C96A—C91A—C9	111.1 (2)	C96B—C95B—H95C	110.1
C92A—C91A—H91A	107.9	C94B—C95B—H95D	110.1
C96A—C91A—H91A	107.9	C96B—C95B—H95D	110.1
C9—C91A—H91A	107.9	H95C—C95B—H95D	108.4
C91A—C92A—C93A	113.0 (2)	C91B—C96B—C95B	109.2 (7)
C91A—C92A—H92A	109.0	C91B—C96B—H96C	109.8
C93A—C92A—H92A	109.0	C95B—C96B—H96C	109.8
C91A—C92A—H92B	109.0	C91B—C96B—H96D	109.8
C93A—C92A—H92B	109.0	C95B—C96B—H96D	109.8
H92A—C92A—H92B	107.8	H96C—C96B—H96D	108.3
C94A—C93A—C92A	111.0 (3)
C6—N1—C2—N3	−0.4 (3)	C4—N9—C9—C91B	−112.0 (6)
N1—C2—N3—C4	−0.6 (3)	C8—N9—C9—C91A	99.4 (2)
C2—N3—C4—N9	−177.5 (2)	C4—N9—C9—C91A	−79.9 (2)
C2—N3—C4—C5	1.1 (3)	N9—C9—C91A—C92A	−66.4 (3)
N3—C4—C5—N7	−178.4 (2)	C91B—C9—C91A—C92A	18.4 (8)
N9—C4—C5—N7	0.5 (2)	N9—C9—C91A—C96A	170.6 (2)
N3—C4—C5—C6	−0.7 (3)	C91B—C9—C91A—C96A	−104.6 (9)
N9—C4—C5—C6	178.1 (1)	C96A—C91A—C92A—C93A	−53.9 (4)
C2—N1—C6—N6	−178.6 (2)	C9—C91A—C92A—C93A	−177.9 (3)
C2—N1—C6—C5	0.8 (3)	C91A—C92A—C93A—C94A	55.4 (4)
C4—C5—C6—N6	179.1 (2)	C92A—C93A—C94A—C95A	−55.3 (4)
N7—C5—C6—N6	−4.0 (3)	C93A—C94A—C95A—C96A	56.4 (4)
C4—C5—C6—N1	−0.3 (3)	C94A—C95A—C96A—C91A	−56.6 (4)
N7—C5—C6—N1	176.6 (2)	C92A—C91A—C96A—C95A	54.4 (3)
N1—C6—N6—C62	177.6 (2)	C9—C91A—C96A—C95A	179.1 (2)
C5—C6—N6—C62	−1.8 (3)	N9—C9—C91B—C92B	65 (1)
N1—C6—N6—C61	−1.4 (3)	C91A—C9—C91B—C92B	−42.0 (8)
C5—C6—N6—C61	179.2 (2)	N9—C9—C91B—C96B	−172.1 (7)
C4—C5—N7—C8	−0.5 (2)	C91A—C9—C91B—C96B	81 (1)
C6—C5—N7—C8	−177.6 (2)	C9—C91B—C92B—C93B	167 (1)
C5—N7—C8—N9	0.4 (2)	C96B—C91B—C92B—C93B	50 (2)
N7—C8—N9—C4	−0.1 (2)	C91B—C92B—C93B—C94B	−51 (2)
N7—C8—N9—C9	−179.5 (2)	C92B—C93B—C94B—C95B	58 (2)
N3—C4—N9—C8	178.6 (2)	C93B—C94B—C95B—C96B	−63 (2)
C5—C4—N9—C8	−0.2 (2)	C9—C91B—C96B—C95B	−177 (1)
N3—C4—N9—C9	−1.9 (3)	C92B—C91B—C96B—C95B	−55 (1)
C5—C4—N9—C9	179.2 (2)	C94B—C95B—C96B—C91B	61 (1)
C8—N9—C9—C91B	67.3 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N3^i	0.93	2.45	3.369 (3)	171

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.