1,1'-[2,3,5,6-Tetra-methyl-p-phenyl-ene-bis(methyl-eneoxy)]di-1H-benzotriazole.

The complete molecule of the title compound, C(24)H(24)N(6)O(2), is generated by a crystallographic inversion centre. The benzotriazole rings form dihedral angles of 2.10 (7)° with the central aromatic ring. The crystal packing is consolidated by π-π inter-actions, with centroid-centroid distances of 3.6234 (10) Å, together with weak C-H⋯π inter-actions.

Related literature

For the biological activity of N-oxide and benzotriazole derivatives see: Katarzyna et al.(2005 ▶); Sarala et al. (2007 ▶). For applications of benzotriazole, see: Kopec et al. (2008 ▶); Krawczyk & Gdaniec (2005 ▶); Smith et al. (2001 ▶); Sha et al. (1996 ▶). For 1-hydroxy­benzotriazole, see: Anderson et al. (1963 ▶); Bosch et al. (1983 ▶).

Experimental

Crystal data

C24H24N6O2

M = 428.49

Monoclinic,

a = 9.3895 (6) Å

b = 7.5960 (2) Å

c = 15.7471 (13) Å

β = 110.770 (3)°

V = 1050.13 (11) Å3

Z = 2

Cu Kα radiation

μ = 0.73 mm−1

T = 193 K

0.51 × 0.26 × 0.19 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (CORINC; Draeger & Gattow, 1971 ▶) T min = 0.707, T max = 0.873

2075 measured reflections

1996 independent reflections

1905 reflections with I > 2σ(I)

R int = 0.026

3 standard reflections frequency: 60 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.147

S = 1.10

1996 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: CORINC (Draeger & Gattow, 1971 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010782/bt2912sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010782/bt2912Isup2.hkl

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

C24H24N6O2	F(000) = 452
Mr = 428.49	Dx = 1.355 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.3895 (6) Å	θ = 65–70°
b = 7.5960 (2) Å	µ = 0.73 mm−1
c = 15.7471 (13) Å	T = 193 K
β = 110.770 (3)°	Block, colourless
V = 1050.13 (11) Å3	0.51 × 0.26 × 0.19 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	1905 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.026
graphite	θmax = 70.0°, θmin = 5.0°
ω/2θ scans	h = −11→10
Absorption correction: ψ scan (CORINC; Draeger & Gattow, 1971)	k = 0→9
Tmin = 0.707, Tmax = 0.873	l = 0→19
2075 measured reflections	3 standard reflections every 60 min
1996 independent reflections	intensity decay: 1%

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0832P)2 + 0.5P] where P = (Fo2 + 2Fc2)/3
1996 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.25022 (16)	−0.07614 (18)	0.47932 (9)	0.0302 (3)
N2	0.17398 (19)	−0.1201 (2)	0.53429 (10)	0.0385 (4)
N3	0.08837 (19)	−0.2555 (2)	0.49841 (11)	0.0408 (4)
C4	0.10897 (19)	−0.2985 (2)	0.41828 (12)	0.0317 (4)
C5	0.0438 (2)	−0.4308 (2)	0.35473 (14)	0.0396 (4)
H5	−0.0276	−0.5118	0.3627	0.047*
C6	0.0873 (2)	−0.4389 (3)	0.28015 (13)	0.0408 (5)
H6	0.0438	−0.5264	0.2353	0.049*
C7	0.1948 (2)	−0.3209 (2)	0.26842 (12)	0.0380 (4)
H7	0.2212	−0.3309	0.2157	0.046*
C8	0.26238 (19)	−0.1922 (2)	0.33068 (12)	0.0321 (4)
H8	0.3367	−0.1146	0.3235	0.039*
C9	0.21514 (17)	−0.1820 (2)	0.40554 (11)	0.0270 (4)
O10	0.34983 (13)	0.06259 (15)	0.50086 (8)	0.0317 (3)
C11	0.27184 (18)	0.2246 (2)	0.45748 (11)	0.0296 (4)
H11A	0.1907	0.2561	0.4812	0.036*
H11B	0.2253	0.2087	0.3909	0.036*
C12	0.39164 (17)	0.3661 (2)	0.48003 (10)	0.0248 (4)
C13	0.47071 (18)	0.3997 (2)	0.42060 (10)	0.0259 (4)
C14	0.42305 (17)	0.4639 (2)	0.55983 (10)	0.0255 (4)
C15	0.4428 (2)	0.2893 (2)	0.33658 (12)	0.0381 (4)
H15A	0.3797	0.3554	0.2830	0.057*
H15B	0.3901	0.1806	0.3416	0.057*
H15C	0.5404	0.2601	0.3305	0.057*
C16	0.3446 (2)	0.4206 (3)	0.62620 (13)	0.0397 (5)
H16A	0.4183	0.4283	0.6884	0.060*
H16B	0.3032	0.3009	0.6147	0.060*
H16C	0.2616	0.5044	0.6185	0.060*

	U11	U22	U33	U12	U13	U23
N1	0.0380 (7)	0.0273 (7)	0.0337 (7)	−0.0030 (6)	0.0229 (6)	0.0022 (5)
N2	0.0543 (9)	0.0351 (8)	0.0403 (8)	−0.0001 (7)	0.0344 (7)	0.0050 (6)
N3	0.0532 (9)	0.0338 (8)	0.0513 (9)	−0.0041 (7)	0.0383 (8)	0.0039 (7)
C4	0.0330 (8)	0.0285 (8)	0.0417 (9)	0.0010 (6)	0.0231 (7)	0.0057 (7)
C5	0.0331 (9)	0.0320 (9)	0.0582 (12)	−0.0044 (7)	0.0219 (8)	−0.0012 (8)
C6	0.0381 (10)	0.0375 (10)	0.0450 (10)	0.0005 (7)	0.0124 (8)	−0.0077 (8)
C7	0.0462 (10)	0.0399 (10)	0.0335 (9)	0.0059 (8)	0.0208 (8)	0.0008 (7)
C8	0.0380 (9)	0.0308 (9)	0.0360 (9)	0.0012 (7)	0.0234 (7)	0.0045 (7)
C9	0.0304 (8)	0.0251 (8)	0.0304 (8)	0.0025 (6)	0.0170 (6)	0.0044 (6)
O10	0.0343 (6)	0.0260 (6)	0.0382 (7)	−0.0022 (5)	0.0170 (5)	0.0013 (5)
C11	0.0316 (8)	0.0272 (8)	0.0344 (8)	0.0003 (6)	0.0171 (7)	0.0021 (6)
C12	0.0304 (7)	0.0243 (8)	0.0253 (7)	0.0010 (6)	0.0170 (6)	0.0016 (6)
C13	0.0354 (8)	0.0266 (8)	0.0223 (7)	0.0033 (6)	0.0184 (6)	0.0001 (6)
C14	0.0325 (8)	0.0284 (8)	0.0241 (7)	0.0040 (6)	0.0204 (6)	0.0037 (6)
C15	0.0540 (11)	0.0389 (10)	0.0312 (9)	−0.0041 (8)	0.0272 (8)	−0.0091 (7)
C16	0.0553 (11)	0.0421 (10)	0.0386 (9)	−0.0027 (8)	0.0375 (9)	0.0024 (8)

N1—N2	1.3465 (18)	C11—C12	1.504 (2)
N1—C9	1.354 (2)	C11—H11A	0.9900
N1—O10	1.3694 (17)	C11—H11B	0.9900
N2—N3	1.304 (2)	C12—C14	1.399 (2)
N3—C4	1.382 (2)	C12—C13	1.409 (2)
C4—C5	1.397 (3)	C13—C14i	1.394 (2)
C4—C9	1.400 (2)	C13—C15	1.509 (2)
C5—C6	1.375 (3)	C14—C13i	1.394 (2)
C5—H5	0.9500	C14—C16	1.5129 (19)
C6—C7	1.410 (3)	C15—H15A	0.9800
C6—H6	0.9500	C15—H15B	0.9800
C7—C8	1.370 (3)	C15—H15C	0.9800
C7—H7	0.9500	C16—H16A	0.9800
C8—C9	1.401 (2)	C16—H16B	0.9800
C8—H8	0.9500	C16—H16C	0.9800
O10—C11	1.4707 (19)
N2—N1—C9	112.41 (14)	C12—C11—H11A	110.5
N2—N1—O10	120.24 (13)	O10—C11—H11B	110.5
C9—N1—O10	127.34 (13)	C12—C11—H11B	110.5
N3—N2—N1	107.67 (14)	H11A—C11—H11B	108.7
N2—N3—C4	108.54 (14)	C14—C12—C13	120.49 (15)
N3—C4—C5	131.05 (16)	C14—C12—C11	119.57 (14)
N3—C4—C9	108.58 (15)	C13—C12—C11	119.94 (14)
C5—C4—C9	120.37 (16)	C14i—C13—C12	119.49 (14)
C6—C5—C4	117.17 (16)	C14i—C13—C15	119.67 (14)
C6—C5—H5	121.4	C12—C13—C15	120.84 (15)
C4—C5—H5	121.4	C13i—C14—C12	119.98 (13)
C5—C6—C7	121.79 (17)	C13i—C14—C16	119.62 (14)
C5—C6—H6	119.1	C12—C14—C16	120.38 (15)
C7—C6—H6	119.1	C13—C15—H15A	109.5
C8—C7—C6	122.08 (16)	C13—C15—H15B	109.5
C8—C7—H7	119.0	H15A—C15—H15B	109.5
C6—C7—H7	119.0	C13—C15—H15C	109.5
C7—C8—C9	115.90 (15)	H15A—C15—H15C	109.5
C7—C8—H8	122.1	H15B—C15—H15C	109.5
C9—C8—H8	122.1	C14—C16—H16A	109.5
N1—C9—C4	102.80 (14)	C14—C16—H16B	109.5
N1—C9—C8	134.53 (15)	H16A—C16—H16B	109.5
C4—C9—C8	122.67 (16)	C14—C16—H16C	109.5
N1—O10—C11	110.19 (11)	H16A—C16—H16C	109.5
O10—C11—C12	106.29 (12)	H16B—C16—H16C	109.5
O10—C11—H11A	110.5
C9—N1—N2—N3	0.3 (2)	C5—C4—C9—C8	−0.7 (3)
O10—N1—N2—N3	−179.78 (14)	C7—C8—C9—N1	−178.85 (17)
N1—N2—N3—C4	−0.5 (2)	C7—C8—C9—C4	1.9 (2)
N2—N3—C4—C5	−179.59 (18)	N2—N1—O10—C11	−92.95 (16)
N2—N3—C4—C9	0.5 (2)	C9—N1—O10—C11	86.90 (18)
N3—C4—C5—C6	179.40 (18)	N1—O10—C11—C12	−176.52 (11)
C9—C4—C5—C6	−0.7 (3)	O10—C11—C12—C14	−88.45 (17)
C4—C5—C6—C7	0.9 (3)	O10—C11—C12—C13	91.90 (16)
C5—C6—C7—C8	0.3 (3)	C14—C12—C13—C14i	−2.3 (3)
C6—C7—C8—C9	−1.6 (3)	C11—C12—C13—C14i	177.30 (13)
N2—N1—C9—C4	−0.03 (18)	C14—C12—C13—C15	177.14 (15)
O10—N1—C9—C4	−179.88 (14)	C11—C12—C13—C15	−3.2 (2)
N2—N1—C9—C8	−179.42 (18)	C13—C12—C14—C13i	2.4 (3)
O10—N1—C9—C8	0.7 (3)	C11—C12—C14—C13i	−177.29 (13)
N3—C4—C9—N1	−0.29 (18)	C13—C12—C14—C16	−176.44 (15)
C5—C4—C9—N1	179.80 (15)	C11—C12—C14—C16	3.9 (2)
N3—C4—C9—C8	179.20 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg2ii	0.95	2.82	3.700 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg2i	0.95	2.82	3.700 (2)	154

Symmetry code: (i) . Cg2 is the centroid of the C4–C9 ring.