N-Benzyl-9-isopropyl-9H-purin-6-amine.

The asymmetric unit of the title compound, C15H17N5, consists of two mol-ecules in which the dihedral angles between the best planes of the purine ring system (r.m.s. deviations = 0.0060 and 0.0190 Å) and the benzene ring are 89.21 (3) and 82.14 (4)°. The mol-ecules within the asymmetric unit are linked into dimers by pairs of N-H⋯N hydrogen bonds. Weak C-H⋯π contacts and π-π inter-actions [centroid-centroid = 3.3071 (1) Å] further connect the mol-ecules into a three-dimensional network.

Related literature

The title compound was prepared according to a modified procedure published by Fiorini & Abel (1998 ▶). For the biological activity of 6,9-disubstituted purines, see: Cappellacci et al. (2011 ▶); Jorda et al. (2011 ▶); Tunçbilek et al. (2009 ▶). For crystallographic data for related compounds, see: Novotná & Trávníček (2013 ▶); Rouchal et al. (2009a ▶,b ▶); Trávníček et al. (2010 ▶).

Experimental

Crystal data

C15H17N5

M = 267.34

Monoclinic,

a = 12.9926 (5) Å

b = 21.1673 (7) Å

c = 11.2622 (6) Å

β = 114.274 (5)°

V = 2823.5 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.50 × 0.38 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire2) diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.942, T max = 1.000

21460 measured reflections

4972 independent reflections

3280 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.058

S = 0.83

4972 reflections

373 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813013500/pk2482sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013500/pk2482Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013500/pk2482Isup3.cml

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

C15H17N5	F(000) = 1136
Mr = 267.34	Dx = 1.258 Mg m−3
Monoclinic, P21/c	Melting point: 390 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.9926 (5) Å	Cell parameters from 6488 reflections
b = 21.1673 (7) Å	θ = 2.9–27.3°
c = 11.2622 (6) Å	µ = 0.08 mm−1
β = 114.274 (5)°	T = 120 K
V = 2823.5 (2) Å3	Pyramid, colourless
Z = 8	0.50 × 0.38 × 0.20 mm

Oxford Diffraction Xcalibur (Sapphire2) diffractometer	4972 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3280 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 8.4353 pixels mm-1	θmax = 25.0°, θmin = 3.3°
ω scan	h = −15→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −25→23
Tmin = 0.942, Tmax = 1.000	l = −13→10
21460 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.029	w = 1/[σ2(Fo2) + (0.0275P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.058	(Δ/σ)max = 0.001
S = 0.83	Δρmax = 0.13 e Å−3
4972 reflections	Δρmin = −0.16 e Å−3
373 parameters

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 > 2σ(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	0.48434 (8)	0.47471 (5)	0.65985 (10)	0.0260 (3)
N2	0.35401 (8)	0.55081 (5)	0.51464 (10)	0.0262 (3)
N3	0.61994 (8)	0.62964 (5)	0.66899 (10)	0.0313 (3)
N4	0.44524 (8)	0.65164 (5)	0.51961 (10)	0.0263 (3)
N5	0.67119 (9)	0.49857 (5)	0.79188 (10)	0.0265 (3)
C1	0.57003 (10)	0.51658 (6)	0.70266 (12)	0.0241 (3)
C2	0.38440 (10)	0.49452 (6)	0.57007 (12)	0.0279 (3)
H2	0.3265	0.4634	0.5419	0.033*
C3	0.44264 (10)	0.59076 (6)	0.55935 (12)	0.0235 (3)
C4	0.54997 (10)	0.57782 (6)	0.65076 (11)	0.0235 (3)
C5	0.55292 (10)	0.67225 (6)	0.58899 (12)	0.0324 (3)
H5	0.5775	0.7136	0.5804	0.039*
C6	0.34853 (10)	0.68646 (6)	0.42406 (12)	0.0264 (3)
H6	0.2996	0.6553	0.3584	0.032*
C7	0.38698 (11)	0.73471 (7)	0.35260 (13)	0.0440 (4)
H7A	0.4339	0.7141	0.3146	0.066*
H7B	0.4310	0.7676	0.4136	0.066*
H7C	0.3210	0.7538	0.2831	0.066*
C8	0.27902 (11)	0.71513 (6)	0.48996 (13)	0.0374 (4)
H8A	0.2602	0.6824	0.5394	0.056*
H8B	0.2093	0.7329	0.4239	0.056*
H8C	0.3224	0.7487	0.5493	0.056*
C9	0.69743 (10)	0.43519 (6)	0.84296 (12)	0.0275 (3)
H9A	0.7664	0.4207	0.8340	0.033*
H9B	0.6349	0.4068	0.7898	0.033*
C10	0.71588 (10)	0.42924 (6)	0.98378 (12)	0.0226 (3)
C11	0.65661 (10)	0.46597 (6)	1.03600 (13)	0.0289 (3)
H11	0.6031	0.4958	0.9824	0.035*
C12	0.67436 (11)	0.45977 (7)	1.16490 (13)	0.0369 (4)
H12	0.6325	0.4850	1.1992	0.044*
C13	0.75233 (11)	0.41715 (7)	1.24409 (14)	0.0381 (4)
H13	0.7646	0.4131	1.3329	0.046*
C14	0.81238 (11)	0.38046 (6)	1.19388 (14)	0.0363 (4)
H14	0.8666	0.3511	1.2481	0.044*
C15	0.79357 (10)	0.38652 (6)	1.06441 (13)	0.0289 (3)
H15	0.8349	0.3608	1.0302	0.035*
N21	1.00117 (8)	0.72864 (5)	0.95195 (10)	0.0239 (3)
N22	1.08432 (8)	0.68113 (5)	1.16590 (9)	0.0236 (3)
N23	0.87221 (8)	0.57374 (5)	0.96305 (10)	0.0279 (3)
N24	0.99893 (8)	0.57966 (5)	1.17200 (10)	0.0256 (3)
N25	0.85603 (9)	0.68204 (5)	0.77541 (10)	0.0260 (3)
C21	0.92837 (9)	0.68029 (6)	0.90160 (12)	0.0220 (3)
C22	1.07258 (10)	0.72557 (6)	1.07788 (12)	0.0252 (3)
H22	1.1224	0.7605	1.1090	0.030*
C23	1.01033 (9)	0.63394 (6)	1.11174 (12)	0.0214 (3)
C24	0.93237 (9)	0.62980 (6)	0.98385 (12)	0.0215 (3)
C25	0.91468 (10)	0.54632 (6)	1.07785 (13)	0.0310 (3)
H25	0.8889	0.5066	1.0940	0.037*
C26	1.05832 (10)	0.56472 (6)	1.31163 (12)	0.0297 (3)
H26	1.1349	0.5846	1.3442	0.036*
C27	1.07405 (11)	0.49430 (6)	1.33211 (13)	0.0417 (4)
H27A	1.1117	0.4776	1.2791	0.063*
H27B	1.0002	0.4740	1.3062	0.063*
H27C	1.1204	0.4856	1.4243	0.063*
C28	0.99545 (12)	0.59390 (7)	1.38523 (14)	0.0486 (4)
H28A	0.9907	0.6397	1.3718	0.073*
H28B	1.0358	0.5847	1.4783	0.073*
H28C	0.9192	0.5761	1.3532	0.073*
C29	0.85268 (10)	0.73381 (6)	0.68906 (12)	0.0278 (3)
H29A	0.8387	0.7163	0.6023	0.033*
H29B	0.9275	0.7546	0.7232	0.033*
C30	0.76355 (10)	0.78312 (6)	0.67322 (12)	0.0246 (3)
C31	0.73658 (10)	0.79940 (6)	0.77588 (13)	0.0307 (3)
H31	0.7761	0.7802	0.8586	0.037*
C32	0.65295 (11)	0.84318 (6)	0.75992 (14)	0.0376 (4)
H32	0.6350	0.8537	0.8312	0.045*
C33	0.59581 (12)	0.87150 (6)	0.64080 (16)	0.0429 (4)
H33	0.5379	0.9013	0.6295	0.051*
C34	0.62262 (11)	0.85664 (6)	0.53779 (15)	0.0405 (4)
H34	0.5840	0.8766	0.4558	0.049*
C35	0.70600 (10)	0.81253 (6)	0.55402 (13)	0.0321 (3)
H35	0.7240	0.8023	0.4827	0.038*
H5N	0.7264 (11)	0.5272 (6)	0.8262 (12)	0.037 (4)*
H25N	0.7954 (10)	0.6558 (6)	0.7491 (12)	0.037 (4)*

	U11	U22	U33	U12	U13	U23
N1	0.0217 (6)	0.0304 (6)	0.0255 (6)	−0.0021 (5)	0.0093 (5)	−0.0038 (5)
N2	0.0209 (6)	0.0308 (7)	0.0259 (7)	−0.0027 (5)	0.0087 (5)	−0.0041 (5)
N3	0.0241 (6)	0.0316 (7)	0.0299 (7)	−0.0035 (5)	0.0026 (5)	0.0040 (6)
N4	0.0201 (6)	0.0298 (7)	0.0243 (6)	0.0000 (5)	0.0043 (5)	0.0002 (5)
N5	0.0222 (6)	0.0272 (7)	0.0248 (7)	−0.0012 (5)	0.0045 (5)	0.0000 (5)
C1	0.0220 (7)	0.0327 (8)	0.0194 (8)	−0.0008 (6)	0.0103 (6)	−0.0048 (6)
C2	0.0223 (7)	0.0328 (8)	0.0292 (8)	−0.0045 (6)	0.0114 (6)	−0.0062 (7)
C3	0.0206 (7)	0.0300 (8)	0.0204 (8)	−0.0003 (6)	0.0090 (6)	−0.0034 (6)
C4	0.0213 (7)	0.0280 (8)	0.0198 (8)	−0.0021 (6)	0.0072 (6)	−0.0017 (6)
C5	0.0236 (7)	0.0333 (8)	0.0328 (9)	−0.0048 (6)	0.0042 (6)	0.0021 (7)
C6	0.0214 (7)	0.0328 (8)	0.0201 (8)	0.0026 (6)	0.0036 (6)	−0.0001 (6)
C7	0.0321 (8)	0.0602 (11)	0.0350 (9)	0.0074 (7)	0.0092 (7)	0.0188 (8)
C8	0.0387 (8)	0.0418 (9)	0.0317 (9)	0.0115 (7)	0.0144 (7)	0.0023 (7)
C9	0.0248 (7)	0.0263 (8)	0.0299 (8)	0.0037 (6)	0.0097 (6)	−0.0034 (6)
C10	0.0199 (7)	0.0197 (7)	0.0274 (8)	−0.0027 (6)	0.0089 (6)	−0.0033 (6)
C11	0.0247 (7)	0.0306 (8)	0.0298 (9)	0.0048 (6)	0.0097 (6)	0.0000 (7)
C12	0.0360 (8)	0.0450 (10)	0.0338 (9)	0.0042 (7)	0.0186 (7)	−0.0038 (7)
C13	0.0426 (9)	0.0442 (9)	0.0302 (9)	−0.0042 (7)	0.0176 (7)	0.0040 (7)
C14	0.0370 (8)	0.0307 (9)	0.0387 (10)	0.0045 (7)	0.0132 (7)	0.0126 (7)
C15	0.0289 (7)	0.0216 (8)	0.0379 (9)	0.0034 (6)	0.0154 (7)	0.0014 (6)
N21	0.0202 (6)	0.0243 (6)	0.0270 (7)	0.0002 (5)	0.0094 (5)	−0.0011 (5)
N22	0.0202 (5)	0.0251 (6)	0.0251 (6)	−0.0022 (5)	0.0090 (5)	−0.0015 (5)
N23	0.0248 (6)	0.0261 (6)	0.0273 (7)	−0.0031 (5)	0.0050 (5)	0.0033 (5)
N24	0.0201 (6)	0.0278 (6)	0.0231 (6)	−0.0041 (5)	0.0029 (5)	0.0037 (5)
N25	0.0223 (6)	0.0270 (7)	0.0245 (7)	−0.0016 (5)	0.0054 (5)	0.0042 (5)
C21	0.0164 (6)	0.0249 (7)	0.0256 (8)	0.0030 (6)	0.0097 (6)	−0.0019 (6)
C22	0.0206 (7)	0.0256 (8)	0.0301 (8)	−0.0015 (6)	0.0112 (6)	−0.0043 (7)
C23	0.0168 (6)	0.0228 (7)	0.0246 (8)	0.0011 (5)	0.0086 (6)	0.0005 (6)
C24	0.0173 (6)	0.0224 (7)	0.0235 (8)	0.0001 (5)	0.0071 (6)	0.0006 (6)
C25	0.0251 (7)	0.0281 (8)	0.0323 (9)	−0.0071 (6)	0.0043 (7)	0.0045 (7)
C26	0.0228 (7)	0.0369 (9)	0.0226 (8)	−0.0038 (6)	0.0023 (6)	0.0069 (6)
C27	0.0379 (8)	0.0416 (9)	0.0370 (9)	0.0032 (7)	0.0065 (7)	0.0145 (7)
C28	0.0530 (10)	0.0584 (11)	0.0321 (9)	0.0091 (8)	0.0151 (8)	0.0064 (8)
C29	0.0286 (7)	0.0310 (8)	0.0243 (8)	0.0016 (6)	0.0114 (6)	0.0043 (6)
C30	0.0228 (7)	0.0248 (8)	0.0260 (8)	−0.0036 (6)	0.0099 (6)	0.0011 (6)
C31	0.0299 (7)	0.0313 (8)	0.0298 (8)	−0.0023 (6)	0.0111 (7)	0.0000 (7)
C32	0.0374 (8)	0.0327 (9)	0.0488 (10)	0.0000 (7)	0.0238 (8)	−0.0045 (8)
C33	0.0343 (8)	0.0288 (9)	0.0654 (12)	0.0067 (7)	0.0203 (8)	0.0028 (8)
C34	0.0380 (9)	0.0313 (9)	0.0468 (10)	0.0057 (7)	0.0119 (8)	0.0120 (8)
C35	0.0325 (8)	0.0315 (8)	0.0324 (9)	−0.0007 (6)	0.0136 (7)	0.0053 (7)

N1—C2	1.3434 (15)	N21—C22	1.3396 (14)
N1—C1	1.3476 (15)	N21—C21	1.3500 (14)
N2—C2	1.3276 (15)	N22—C22	1.3291 (14)
N2—C3	1.3482 (14)	N22—C23	1.3460 (14)
N3—C5	1.3185 (15)	N23—C25	1.3138 (14)
N3—C4	1.3851 (14)	N23—C24	1.3869 (14)
N4—C5	1.3635 (14)	N24—C25	1.3661 (14)
N4—C3	1.3693 (15)	N24—C23	1.3730 (14)
N4—C6	1.4725 (14)	N24—C26	1.4733 (14)
N5—C1	1.3404 (15)	N25—C21	1.3440 (15)
N5—C9	1.4441 (14)	N25—C29	1.4539 (15)
N5—H5N	0.897 (12)	N25—H25N	0.908 (12)
C1—C4	1.4017 (16)	C21—C24	1.4012 (16)
C2—H2	0.9500	C22—H22	0.9500
C3—C4	1.3781 (15)	C23—C24	1.3815 (15)
C5—H5	0.9500	C25—H25	0.9500
C6—C7	1.5069 (17)	C26—C27	1.5093 (17)
C6—C8	1.5119 (16)	C26—C28	1.5141 (18)
C6—H6	1.0000	C26—H26	1.0000
C7—H7A	0.9800	C27—H27A	0.9800
C7—H7B	0.9800	C27—H27B	0.9800
C7—H7C	0.9800	C27—H27C	0.9800
C8—H8A	0.9800	C28—H28A	0.9800
C8—H8B	0.9800	C28—H28B	0.9800
C8—H8C	0.9800	C28—H28C	0.9800
C9—C10	1.5086 (16)	C29—C30	1.5141 (16)
C9—H9A	0.9900	C29—H29A	0.9900
C9—H9B	0.9900	C29—H29B	0.9900
C10—C15	1.3811 (16)	C30—C31	1.3826 (17)
C10—C11	1.3842 (16)	C30—C35	1.3869 (16)
C11—C12	1.3794 (17)	C31—C32	1.3825 (17)
C11—H11	0.9500	C31—H31	0.9500
C12—C13	1.3757 (17)	C32—C33	1.3753 (18)
C12—H12	0.9500	C32—H32	0.9500
C13—C14	1.3764 (18)	C33—C34	1.3778 (19)
C13—H13	0.9500	C33—H33	0.9500
C14—C15	1.3818 (17)	C34—C35	1.3841 (17)
C14—H14	0.9500	C34—H34	0.9500
C15—H15	0.9500	C35—H35	0.9500
C2—N1—C1	117.70 (11)	C22—N21—C21	117.94 (11)
C2—N2—C3	110.12 (10)	C22—N22—C23	110.22 (10)
C5—N3—C4	103.39 (10)	C25—N23—C24	103.43 (10)
C5—N4—C3	105.74 (10)	C25—N24—C23	105.28 (10)
C5—N4—C6	128.68 (11)	C25—N24—C26	128.21 (11)
C3—N4—C6	125.56 (10)	C23—N24—C26	126.27 (10)
C1—N5—C9	124.12 (11)	C21—N25—C29	122.94 (11)
C1—N5—H5N	119.7 (8)	C21—N25—H25N	117.6 (8)
C9—N5—H5N	116.1 (8)	C29—N25—H25N	117.3 (8)
N5—C1—N1	119.51 (12)	N25—C21—N21	119.20 (12)
N5—C1—C4	122.18 (11)	N25—C21—C24	122.67 (11)
N1—C1—C4	118.31 (11)	N21—C21—C24	118.13 (11)
N2—C2—N1	129.98 (12)	N22—C22—N21	129.88 (11)
N2—C2—H2	115.0	N22—C22—H22	115.1
N1—C2—H2	115.0	N21—C22—H22	115.1
N2—C3—N4	126.89 (11)	N22—C23—N24	126.80 (11)
N2—C3—C4	126.94 (12)	N22—C23—C24	126.90 (12)
N4—C3—C4	106.13 (11)	N24—C23—C24	106.28 (10)
C3—C4—N3	110.75 (11)	C23—C24—N23	110.56 (11)
C3—C4—C1	116.93 (11)	C23—C24—C21	116.92 (11)
N3—C4—C1	132.26 (11)	N23—C24—C21	132.52 (11)
N3—C5—N4	113.99 (12)	N23—C25—N24	114.45 (11)
N3—C5—H5	123.0	N23—C25—H25	122.8
N4—C5—H5	123.0	N24—C25—H25	122.8
N4—C6—C7	111.03 (10)	N24—C26—C27	110.72 (11)
N4—C6—C8	110.17 (10)	N24—C26—C28	109.45 (11)
C7—C6—C8	112.72 (11)	C27—C26—C28	112.88 (12)
N4—C6—H6	107.6	N24—C26—H26	107.9
C7—C6—H6	107.6	C27—C26—H26	107.9
C8—C6—H6	107.6	C28—C26—H26	107.9
C6—C7—H7A	109.5	C26—C27—H27A	109.5
C6—C7—H7B	109.5	C26—C27—H27B	109.5
H7A—C7—H7B	109.5	H27A—C27—H27B	109.5
C6—C7—H7C	109.5	C26—C27—H27C	109.5
H7A—C7—H7C	109.5	H27A—C27—H27C	109.5
H7B—C7—H7C	109.5	H27B—C27—H27C	109.5
C6—C8—H8A	109.5	C26—C28—H28A	109.5
C6—C8—H8B	109.5	C26—C28—H28B	109.5
H8A—C8—H8B	109.5	H28A—C28—H28B	109.5
C6—C8—H8C	109.5	C26—C28—H28C	109.5
H8A—C8—H8C	109.5	H28A—C28—H28C	109.5
H8B—C8—H8C	109.5	H28B—C28—H28C	109.5
N5—C9—C10	113.94 (10)	N25—C29—C30	114.18 (11)
N5—C9—H9A	108.8	N25—C29—H29A	108.7
C10—C9—H9A	108.8	C30—C29—H29A	108.7
N5—C9—H9B	108.8	N25—C29—H29B	108.7
C10—C9—H9B	108.8	C30—C29—H29B	108.7
H9A—C9—H9B	107.7	H29A—C29—H29B	107.6
C15—C10—C11	118.18 (12)	C31—C30—C35	118.45 (12)
C15—C10—C9	120.21 (11)	C31—C30—C29	121.18 (11)
C11—C10—C9	121.60 (11)	C35—C30—C29	120.36 (12)
C12—C11—C10	120.81 (12)	C32—C31—C30	120.95 (13)
C12—C11—H11	119.6	C32—C31—H31	119.5
C10—C11—H11	119.6	C30—C31—H31	119.5
C13—C12—C11	120.31 (13)	C33—C32—C31	119.95 (14)
C13—C12—H12	119.8	C33—C32—H32	120.0
C11—C12—H12	119.8	C31—C32—H32	120.0
C12—C13—C14	119.63 (13)	C32—C33—C34	119.99 (13)
C12—C13—H13	120.2	C32—C33—H33	120.0
C14—C13—H13	120.2	C34—C33—H33	120.0
C13—C14—C15	119.79 (13)	C33—C34—C35	119.86 (14)
C13—C14—H14	120.1	C33—C34—H34	120.1
C15—C14—H14	120.1	C35—C34—H34	120.1
C10—C15—C14	121.27 (12)	C34—C35—C30	120.79 (13)
C10—C15—H15	119.4	C34—C35—H35	119.6
C14—C15—H15	119.4	C30—C35—H35	119.6

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···N23	0.896 (13)	2.129 (11)	2.9883 (13)	160.2 (12)
N25—H25N···N3	0.908 (12)	2.151 (12)	3.0088 (15)	157.2 (12)
C25—H25···Cg1	0.95	2.76	3.6413 (14)	156
C5—H5···Cg2	0.95	2.72	3.6179 (13)	158
C12—H12···Cg3i	0.95	2.93	3.6703 (17)	135
C15—H15···Cg4ii	0.95	2.60	3.5158 (15)	161
Cg3···Cg3iii			3.3071 (1)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are centroids of the C10–C15, C30–C35, N1/N2/C1–C4 and N21/N22/C21–C24 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5N⋯N23	0.896 (13)	2.129 (11)	2.9883 (13)	160.2 (12)
N25—H25N⋯N3	0.908 (12)	2.151 (12)	3.0088 (15)	157.2 (12)
C25—H25⋯Cg1	0.95	2.76	3.6413 (14)	156
C5—H5⋯Cg2	0.95	2.72	3.6179 (13)	158
C12—H12⋯Cg3i	0.95	2.93	3.6703 (17)	135
C15—H15⋯Cg4ii	0.95	2.60	3.5158 (15)	161

Symmetry codes: (i) ; (ii) .