5,5'-Di-4-pyridyl-2,2'-(5-tert-butyl-m-phenyl-ene)bis-(1,3,4-oxadiazole).

The title compound, C(24)H(20)N(6)O(2), is a novel 1,3,4-oxadiazole derivative which has potential as an electron-transporting material in organic electroluminescent (EL) devices. In the crystal, the mol-ecular framework is almost planar with an r.m.s. deviation of 0.091 (4) Å and it exists in an E form. Intra-molecular C-H⋯O and C-H⋯N hydrogen bonds are observed between the benzene and 1,3,4-oxadiazole rings. The tert-butyl group is disordered over two sites, with occupancy factors of 0.78 (1) and 0.22 (1) for the major and minor orientations, respectively. In the crystal structure, mol-ecules aggregate via C-H⋯N inter-actions, forming mol-ecular tapes along the b axis, which aggregate to form a mol-ecular sheet via C-H⋯N inter-actions.

Related literature

The application of 1,3,4-oxadiazole derivatives as electron-transporting materials in EL devices has been reported by Hughes & Bryce (2005 ▶). For related structures, including the 1,3,4-oxadiazole system, see: Ono et al.(2005 ▶, 2008 ▶).

Experimental

Crystal data

C24H20N6O2

M = 424.46

Monoclinic,

a = 5.8778 (10) Å

b = 14.767 (3) Å

c = 25.298 (6) Å

β = 90.635 (10)°

V = 2195.7 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.25 × 0.13 × 0.10 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: none

16667 measured reflections

4956 independent reflections

1548 reflections with I > 2σ(I)

R int = 0.112

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.172

S = 0.90

4956 reflections

323 parameters

16 restraints

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: TEXSAN (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027056/rn2057sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027056/rn2057Isup2.hkl

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

C24H20N6O2	F(000) = 888
Mr = 424.46	Dx = 1.284 Mg m−3
Monoclinic, P21/c	Melting point: 529 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71070 Å
a = 5.8778 (10) Å	Cell parameters from 1816 reflections
b = 14.767 (3) Å	θ = 3.2–27.5°
c = 25.298 (6) Å	µ = 0.09 mm−1
β = 90.635 (10)°	T = 296 K
V = 2195.7 (8) Å3	Prism, yellow
Z = 4	0.25 × 0.13 × 0.10 mm

Rigaku Mercury CCD diffractometer	1548 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.112
graphite monochromator	θmax = 27.5°, θmin = 3.2°
Detector resolution: 14.62 pixels mm-1	h = −5→7
φ and ω scans	k = −19→14
16667 measured reflections	l = −32→22
4956 independent reflections

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H-atom parameters constrained
S = 0.90	w = 1/[σ2(Fo2) + (0.0474P)2] where P = (Fo2 + 2Fc2)/3
4956 reflections	(Δ/σ)max = 0.004
323 parameters	Δρmax = 0.23 e Å−3
16 restraints	Δρmin = −0.13 e Å−3

Experimental. 1H NMR (DMSO-d6, δ p.p.m.): 1.46 (s, 9H), 8.15 (d, J = 5.5 Hz, 4H), 8.36 (s, 2H), 8.61 (s, 1H), 8.88 (d, J = 5.5 Hz, 4H); MS (EI): m/z 424 (M+), 409.

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. Three methyl groups of the tert-butyl group are disordered over two sites (C22–C24 and C25–C27) with occupancies of 0.78 (1):0.22 (1). The values were determined by refining site occupancies.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	Occ. (<1)
O1	0.3004 (4)	0.22049 (16)	0.28302 (10)	0.0597 (7)
O2	−0.4436 (4)	0.45678 (17)	0.41002 (9)	0.0615 (8)
N1	0.4194 (5)	0.3569 (2)	0.26015 (14)	0.0762 (11)
N2	0.2304 (5)	0.3662 (2)	0.29375 (13)	0.0731 (11)
N3	0.9831 (6)	0.1428 (3)	0.17039 (15)	0.0904 (12)
N4	−0.6818 (5)	0.3527 (2)	0.43895 (13)	0.0726 (10)
N5	−0.7648 (5)	0.4388 (2)	0.45273 (14)	0.0734 (11)
N6	−0.6473 (7)	0.7838 (2)	0.45477 (15)	0.0903 (12)
C1	−0.2506 (6)	0.1407 (3)	0.37961 (15)	0.0586 (11)
C2	−0.0691 (6)	0.1670 (2)	0.34870 (15)	0.0587 (11)
H2	0.0240	0.1228	0.3342	0.070*
C3	−0.0221 (6)	0.2581 (2)	0.33868 (15)	0.0541 (10)
C4	−0.1606 (6)	0.3249 (3)	0.36019 (14)	0.0584 (11)
H4	−0.1300	0.3858	0.3540	0.070*
C5	−0.3437 (6)	0.3001 (2)	0.39072 (14)	0.0537 (11)
C6	−0.3841 (6)	0.2088 (3)	0.40024 (15)	0.0620 (11)
H6	−0.5062	0.1929	0.4214	0.074*
C7	0.1671 (6)	0.2853 (3)	0.30558 (15)	0.0588 (11)
C8	0.4546 (7)	0.2716 (3)	0.25547 (16)	0.0592 (11)
C9	0.6312 (6)	0.2249 (3)	0.22503 (15)	0.0587 (11)
C10	0.6450 (7)	0.1324 (3)	0.22164 (16)	0.0752 (13)
H10	0.5367	0.0957	0.2375	0.090*
C11	0.8243 (8)	0.0949 (3)	0.19406 (18)	0.0893 (16)
H11	0.8334	0.0321	0.1921	0.107*
C12	0.9652 (7)	0.2322 (4)	0.17330 (18)	0.0845 (15)
H12	1.0737	0.2672	0.1563	0.101*
C13	0.7938 (7)	0.2763 (3)	0.20023 (15)	0.0716 (13)
H13	0.7887	0.3392	0.2015	0.086*
C14	−0.4945 (7)	0.3669 (3)	0.41435 (15)	0.0587 (11)
C15	−0.6198 (6)	0.4971 (3)	0.43581 (14)	0.0571 (11)
C16	−0.6269 (6)	0.5958 (3)	0.44115 (14)	0.0577 (11)
C17	−0.8051 (6)	0.6360 (3)	0.46777 (15)	0.0709 (13)
H17	−0.9210	0.6009	0.4819	0.085*
C18	−0.8076 (7)	0.7293 (3)	0.47298 (17)	0.0782 (14)
H18	−0.9297	0.7554	0.4904	0.094*
C19	−0.4754 (8)	0.7431 (3)	0.42957 (19)	0.0953 (16)
H19	−0.3601	0.7796	0.4164	0.114*
C20	−0.4581 (7)	0.6506 (3)	0.42176 (16)	0.0746 (13)
H20	−0.3352	0.6261	0.4038	0.090*
C21	−0.2996 (7)	0.0404 (3)	0.3923 (2)	0.0689 (12)
C22	−0.2044 (17)	0.0225 (5)	0.4471 (3)	0.104 (3)	0.781 (13)
H22A	−0.2842	0.0588	0.4724	0.156*	0.781 (13)
H22B	−0.0457	0.0377	0.4482	0.156*	0.781 (13)
H22C	−0.2231	−0.0404	0.4557	0.156*	0.781 (13)
C23	−0.5473 (10)	0.0201 (4)	0.3857 (5)	0.138 (6)	0.781 (13)
H23A	−0.5737	−0.0429	0.3925	0.207*	0.781 (13)
H23B	−0.5946	0.0342	0.3502	0.207*	0.781 (13)
H23C	−0.6329	0.0561	0.4100	0.207*	0.781 (13)
C24	−0.1655 (15)	−0.0238 (4)	0.3541 (3)	0.092 (3)	0.781 (13)
H24A	−0.2110	−0.0854	0.3600	0.139*	0.781 (13)
H24B	−0.0051	−0.0179	0.3609	0.139*	0.781 (13)
H24C	−0.1984	−0.0074	0.3181	0.139*	0.781 (13)
C25	−0.393 (5)	−0.0078 (13)	0.3436 (7)	0.080 (11)	0.219 (13)
H25A	−0.5298	−0.0398	0.3526	0.121*	0.219 (13)
H25B	−0.2824	−0.0500	0.3309	0.121*	0.219 (13)
H25C	−0.4270	0.0358	0.3165	0.121*	0.219 (13)
C26	−0.116 (6)	−0.0169 (19)	0.419 (2)	0.20 (3)	0.219 (13)
H26A	−0.1786	−0.0467	0.4492	0.303*	0.219 (13)
H26B	0.0077	0.0212	0.4298	0.303*	0.219 (13)
H26C	−0.0624	−0.0614	0.3943	0.303*	0.219 (13)
C27	−0.483 (5)	0.0375 (17)	0.4371 (11)	0.125 (15)	0.219 (13)
H27A	−0.6150	0.0714	0.4261	0.187*	0.219 (13)
H27B	−0.4211	0.0636	0.4689	0.187*	0.219 (13)
H27C	−0.5261	−0.0242	0.4437	0.187*	0.219 (13)

	U11	U22	U33	U12	U13	U23
O1	0.0732 (17)	0.0460 (16)	0.0602 (18)	0.0062 (14)	0.0133 (14)	0.0036 (14)
O2	0.0596 (17)	0.0577 (18)	0.0676 (19)	−0.0027 (14)	0.0171 (14)	−0.0041 (15)
N1	0.086 (3)	0.051 (2)	0.092 (3)	0.002 (2)	0.025 (2)	0.013 (2)
N2	0.077 (2)	0.051 (2)	0.092 (3)	0.0021 (19)	0.030 (2)	0.010 (2)
N3	0.099 (3)	0.086 (3)	0.087 (3)	0.008 (3)	0.022 (2)	−0.001 (3)
N4	0.069 (2)	0.064 (2)	0.085 (3)	−0.0093 (19)	0.021 (2)	−0.009 (2)
N5	0.066 (2)	0.066 (2)	0.089 (3)	−0.008 (2)	0.027 (2)	−0.006 (2)
N6	0.119 (3)	0.067 (3)	0.086 (3)	0.000 (2)	0.030 (2)	−0.004 (2)
C1	0.061 (3)	0.052 (3)	0.063 (3)	−0.004 (2)	−0.001 (2)	0.000 (2)
C2	0.062 (3)	0.048 (3)	0.065 (3)	0.0057 (19)	0.000 (2)	−0.007 (2)
C3	0.059 (3)	0.045 (2)	0.058 (3)	0.003 (2)	0.005 (2)	−0.001 (2)
C4	0.066 (3)	0.052 (3)	0.057 (3)	−0.006 (2)	−0.001 (2)	0.002 (2)
C5	0.062 (3)	0.047 (3)	0.052 (3)	−0.004 (2)	0.006 (2)	−0.005 (2)
C6	0.060 (3)	0.068 (3)	0.059 (3)	−0.014 (2)	0.007 (2)	0.005 (2)
C7	0.066 (3)	0.050 (3)	0.060 (3)	0.002 (2)	0.009 (2)	0.007 (2)
C8	0.069 (3)	0.054 (3)	0.055 (3)	−0.006 (2)	0.011 (2)	0.019 (2)
C9	0.073 (3)	0.058 (3)	0.046 (3)	0.002 (2)	0.009 (2)	0.005 (2)
C10	0.099 (3)	0.059 (3)	0.068 (3)	0.002 (3)	0.023 (3)	0.001 (3)
C11	0.116 (4)	0.066 (3)	0.086 (4)	0.015 (3)	0.026 (3)	−0.001 (3)
C12	0.087 (4)	0.081 (4)	0.086 (4)	−0.002 (3)	0.026 (3)	0.009 (3)
C13	0.086 (3)	0.054 (3)	0.075 (3)	0.001 (2)	0.015 (3)	0.009 (2)
C14	0.065 (3)	0.050 (3)	0.062 (3)	−0.008 (2)	0.006 (2)	−0.003 (2)
C15	0.053 (3)	0.063 (3)	0.056 (3)	−0.002 (2)	0.014 (2)	−0.006 (2)
C16	0.063 (3)	0.065 (3)	0.045 (3)	−0.001 (2)	0.011 (2)	−0.002 (2)
C17	0.069 (3)	0.072 (3)	0.073 (3)	−0.004 (2)	0.019 (2)	−0.007 (3)
C18	0.086 (3)	0.068 (3)	0.081 (3)	0.013 (3)	0.019 (3)	−0.007 (3)
C19	0.116 (4)	0.070 (4)	0.101 (4)	−0.008 (3)	0.040 (3)	0.005 (3)
C20	0.078 (3)	0.068 (3)	0.079 (3)	−0.002 (3)	0.028 (2)	0.001 (3)
C21	0.077 (3)	0.045 (3)	0.086 (4)	0.002 (2)	0.011 (3)	0.010 (3)
C22	0.154 (9)	0.051 (5)	0.107 (7)	0.007 (5)	−0.004 (6)	0.027 (5)
C23	0.056 (4)	0.052 (5)	0.305 (19)	−0.018 (3)	−0.024 (7)	0.032 (8)
C24	0.123 (8)	0.046 (4)	0.108 (6)	−0.020 (4)	0.003 (6)	−0.009 (4)
C25	0.13 (3)	0.044 (13)	0.065 (16)	−0.022 (16)	−0.008 (16)	0.002 (11)
C26	0.22 (4)	0.06 (2)	0.32 (8)	0.04 (2)	−0.17 (5)	−0.01 (3)
C27	0.21 (4)	0.09 (2)	0.07 (2)	−0.05 (2)	0.02 (2)	−0.013 (17)

O1—C7	1.366 (4)	C13—H13	0.9300
O1—C8	1.375 (4)	C15—C16	1.465 (5)
O2—C15	1.367 (4)	C16—C17	1.385 (4)
O2—C14	1.365 (4)	C16—C20	1.375 (5)
N1—C8	1.282 (4)	C17—C18	1.384 (5)
N1—N2	1.413 (4)	C17—H17	0.9300
N2—C7	1.287 (4)	C18—H18	0.9300
N3—C11	1.320 (5)	C19—C20	1.384 (5)
N3—C12	1.326 (5)	C19—H19	0.9300
N4—C14	1.288 (4)	C20—H20	0.9300
N4—N5	1.407 (4)	C21—C22	1.513 (7)
N5—C15	1.288 (4)	C21—C23	1.494 (6)
N6—C18	1.326 (4)	C21—C24	1.573 (6)
N6—C19	1.343 (5)	C21—C25	1.523 (13)
C1—C2	1.385 (5)	C21—C26	1.521 (14)
C1—C6	1.382 (5)	C21—C27	1.575 (11)
C1—C21	1.542 (5)	C22—H22A	0.9600
C2—C3	1.396 (4)	C22—H22B	0.9600
C2—H2	0.9300	C22—H22C	0.9600
C3—C4	1.394 (4)	C23—H23A	0.9600
C3—C7	1.456 (5)	C23—H23B	0.9600
C4—C5	1.381 (4)	C23—H23C	0.9600
C4—H4	0.9300	C24—H24A	0.9600
C5—C6	1.390 (4)	C24—H24B	0.9600
C5—C14	1.458 (4)	C24—H24C	0.9600
C6—H6	0.9300	C25—H25A	0.9600
C8—C9	1.471 (5)	C25—H25B	0.9600
C9—C13	1.377 (4)	C25—H25C	0.9600
C9—C10	1.371 (5)	C26—H26A	0.9600
C10—C11	1.386 (5)	C26—H26B	0.9600
C10—H10	0.9300	C26—H26C	0.9600
C11—H11	0.9300	C27—H27A	0.9600
C12—C13	1.384 (5)	C27—H27B	0.9600
C12—H12	0.9300	C27—H27C	0.9600
C7—O1—C8	102.2 (3)	N5—C15—C16	128.0 (4)
C15—O2—C14	102.5 (3)	O2—C15—C16	120.0 (3)
C8—N1—N2	106.3 (3)	C17—C16—C20	118.3 (4)
C7—N2—N1	106.3 (3)	C17—C16—C15	119.6 (4)
C11—N3—C12	116.8 (4)	C20—C16—C15	122.1 (4)
C14—N4—N5	105.9 (3)	C16—C17—C18	118.8 (4)
C15—N5—N4	106.8 (3)	C16—C17—H17	120.6
C18—N6—C19	115.7 (4)	C18—C17—H17	120.6
C2—C1—C6	116.9 (4)	N6—C18—C17	124.3 (4)
C2—C1—C21	122.3 (4)	N6—C18—H18	117.9
C6—C1—C21	120.8 (3)	C17—C18—H18	117.9
C1—C2—C3	121.9 (3)	N6—C19—C20	124.5 (4)
C1—C2—H2	119.0	N6—C19—H19	117.7
C3—C2—H2	119.0	C20—C19—H19	117.7
C4—C3—C2	119.5 (3)	C16—C20—C19	118.4 (4)
C4—C3—C7	118.8 (3)	C16—C20—H20	120.8
C2—C3—C7	121.7 (3)	C19—C20—H20	120.8
C5—C4—C3	119.5 (4)	C23—C21—C22	114.7 (6)
C5—C4—H4	120.2	C23—C21—C1	110.7 (4)
C3—C4—H4	120.2	C22—C21—C1	106.9 (4)
C4—C5—C6	119.3 (3)	C23—C21—C24	107.7 (6)
C4—C5—C14	122.0 (4)	C22—C21—C24	106.0 (5)
C6—C5—C14	118.6 (3)	C1—C21—C24	110.8 (4)
C5—C6—C1	122.8 (3)	C21—C22—H22A	109.4
C5—C6—H6	118.6	C21—C22—H22B	109.5
C1—C6—H6	118.6	C21—C22—H22C	109.5
N2—C7—O1	112.6 (3)	C21—C23—H23A	109.5
N2—C7—C3	127.9 (4)	C21—C23—H23B	109.4
O1—C7—C3	119.4 (3)	C21—C23—H23C	109.5
N1—C8—O1	112.6 (3)	C21—C24—H24A	109.5
N1—C8—C9	128.7 (3)	C21—C24—H24B	109.5
O1—C8—C9	118.7 (3)	C21—C24—H24C	109.5
C13—C9—C10	118.6 (4)	C21—C25—H25A	109.6
C13—C9—C8	118.5 (4)	C21—C25—H25B	109.4
C10—C9—C8	122.9 (4)	H25A—C25—H25B	109.5
C9—C10—C11	118.4 (4)	C21—C25—H25C	109.5
C9—C10—H10	120.8	H25A—C25—H25C	109.5
C11—C10—H10	120.8	H25B—C25—H25C	109.5
N3—C11—C10	124.0 (4)	C21—C26—H26A	109.3
N3—C11—H11	118.0	C21—C26—H26B	109.5
C10—C11—H11	118.0	H26A—C26—H26B	109.5
N3—C12—C13	123.6 (4)	C21—C26—H26C	109.6
N3—C12—H12	118.2	H26A—C26—H26C	109.5
C13—C12—H12	118.2	H26B—C26—H26C	109.5
C9—C13—C12	118.5 (4)	C21—C27—H27A	109.4
C9—C13—H13	120.7	C21—C27—H27B	109.6
C12—C13—H13	120.7	H27A—C27—H27B	109.5
N4—C14—O2	112.7 (3)	C21—C27—H27C	109.5
N4—C14—C5	127.9 (4)	H27A—C27—H27C	109.5
O2—C14—C5	119.3 (3)	H27B—C27—H27C	109.5
N5—C15—O2	112.0 (4)
C8—N1—N2—C7	−0.9 (5)	C11—N3—C12—C13	1.2 (8)
C14—N4—N5—C15	−0.7 (4)	C10—C9—C13—C12	−0.5 (6)
C6—C1—C2—C3	0.0 (6)	C8—C9—C13—C12	177.5 (4)
C21—C1—C2—C3	−178.1 (4)	N3—C12—C13—C9	−0.7 (7)
C1—C2—C3—C4	0.0 (6)	N5—N4—C14—O2	−0.3 (5)
C1—C2—C3—C7	−179.2 (4)	N5—N4—C14—C5	−178.5 (4)
C2—C3—C4—C5	−0.6 (6)	C15—O2—C14—N4	1.1 (4)
C7—C3—C4—C5	178.6 (4)	C15—O2—C14—C5	179.4 (3)
C3—C4—C5—C6	1.2 (6)	C4—C5—C14—N4	172.5 (4)
C3—C4—C5—C14	179.9 (4)	C6—C5—C14—N4	−8.7 (6)
C4—C5—C6—C1	−1.2 (6)	C4—C5—C14—O2	−5.5 (6)
C14—C5—C6—C1	−180.0 (4)	C6—C5—C14—O2	173.2 (3)
C2—C1—C6—C5	0.6 (6)	N4—N5—C15—O2	1.4 (5)
C21—C1—C6—C5	178.7 (4)	N4—N5—C15—C16	−178.9 (4)
N1—N2—C7—O1	0.7 (5)	C14—O2—C15—N5	−1.5 (4)
N1—N2—C7—C3	−179.2 (4)	C14—O2—C15—C16	178.7 (4)
C8—O1—C7—N2	−0.2 (4)	N5—C15—C16—C17	0.9 (7)
C8—O1—C7—C3	179.7 (4)	O2—C15—C16—C17	−179.4 (3)
C4—C3—C7—N2	1.7 (7)	N5—C15—C16—C20	179.0 (4)
C2—C3—C7—N2	−179.1 (4)	O2—C15—C16—C20	−1.3 (6)
C4—C3—C7—O1	−178.2 (3)	C20—C16—C17—C18	1.0 (6)
C2—C3—C7—O1	1.0 (6)	C15—C16—C17—C18	179.2 (4)
N2—N1—C8—O1	0.9 (5)	C19—N6—C18—C17	0.5 (7)
N2—N1—C8—C9	−179.8 (4)	C16—C17—C18—N6	−1.1 (7)
C7—O1—C8—N1	−0.5 (5)	C18—N6—C19—C20	0.2 (8)
C7—O1—C8—C9	−179.9 (3)	C17—C16—C20—C19	−0.4 (6)
N1—C8—C9—C13	4.7 (7)	C15—C16—C20—C19	−178.5 (4)
O1—C8—C9—C13	−176.0 (4)	N6—C19—C20—C16	−0.3 (8)
N1—C8—C9—C10	−177.4 (5)	C2—C1—C21—C23	−135.0 (7)
O1—C8—C9—C10	1.9 (6)	C6—C1—C21—C23	47.0 (8)
C13—C9—C10—C11	1.0 (7)	C2—C1—C21—C22	99.4 (6)
C8—C9—C10—C11	−176.9 (4)	C6—C1—C21—C22	−78.6 (6)
C12—N3—C11—C10	−0.7 (7)	C2—C1—C21—C24	−15.6 (7)
C9—C10—C11—N3	−0.4 (7)	C6—C1—C21—C24	166.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.54	2.860 (4)	101
C6—H6···N4	0.93	2.61	2.928 (5)	100
C11—H11···N2i	0.93	2.50	3.406 (6)	164
C17—H17···N5ii	0.93	2.56	3.430 (5)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1	0.93	2.54	2.860 (4)	101
C6—H6⋯N4	0.93	2.61	2.928 (5)	100
C11—H11⋯N2i	0.93	2.50	3.406 (6)	164
C17—H17⋯N5ii	0.93	2.56	3.430 (5)	156

Symmetry codes: (i) ; (ii) .