(E)-2-(2H-Benzotriazol-2-yl)-4-methyl-6-(phenyl-imino-meth-yl)phenol.

In the title compound, C(20)H(16)N(4)O, the non-H atoms of the benzotriazole ring system and those of the methyl-phenol group are essentially coplanar, with an r.m.s. deviation of 0.004 (2) Å. The mean plane of these atoms forms a dihedral angle of 60.9 (2)° with the phenyl ring. There is an intra-molecular O-H⋯N hydrogen bond between the phenol and benzotriazole groups.

Related literature

For related structures, see: Chen et al. (2010 ▶); Li et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C20H16N4O

M = 328.37

Monoclinic,

a = 15.7279 (5) Å

b = 12.3002 (4) Å

c = 8.4903 (3) Å

β = 104.842 (1)°

V = 1587.70 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.48 × 0.37 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.959, T max = 0.982

15472 measured reflections

3924 independent reflections

2874 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.143

S = 1.01

3924 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810040468/lh5146sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040468/lh5146Isup2.hkl

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

C20H16N4O	F(000) = 688
Mr = 328.37	Dx = 1.374 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5818 reflections
a = 15.7279 (5) Å	θ = 2.7–28.2°
b = 12.3002 (4) Å	µ = 0.09 mm−1
c = 8.4903 (3) Å	T = 173 K
β = 104.842 (1)°	Block, yellow
V = 1587.70 (9) Å3	0.48 × 0.37 × 0.21 mm
Z = 4

Bruker APEXII CCD diffractometer	3924 independent reflections
Radiation source: fine-focus sealed tube	2874 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 8.3333 pixels mm-1	θmax = 28.3°, θmin = 2.1°
φ and ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −16→16
Tmin = 0.959, Tmax = 0.982	l = −11→10
15472 measured 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0585P)2 + 1.1196P] where P = (Fo2 + 2Fc2)/3
3924 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. 1H NMR (CDCl3, ppm): δ 8.77 (s, 1H, PhN=CH), 7.31-8.03 (m, 11H, PhH), 2.45 (s, 3H, PhCH3).

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
O	0.33970 (8)	0.05791 (10)	0.32102 (16)	0.0282 (3)
H0A	0.3839	0.0749	0.3960	0.042*
N1	0.44430 (10)	0.18656 (12)	0.52339 (19)	0.0261 (3)
N2	0.39775 (10)	0.27027 (12)	0.44505 (18)	0.0237 (3)
N3	0.42414 (10)	0.36903 (12)	0.50100 (19)	0.0260 (3)
N4	0.12957 (11)	0.00970 (13)	−0.0541 (2)	0.0300 (4)
C1	0.29886 (11)	0.14915 (14)	0.2511 (2)	0.0236 (4)
C2	0.32445 (11)	0.25450 (14)	0.3077 (2)	0.0236 (4)
C3	0.27847 (12)	0.34491 (14)	0.2315 (2)	0.0255 (4)
H3B	0.2969	0.4155	0.2713	0.031*
C4	0.20630 (12)	0.33396 (14)	0.0987 (2)	0.0262 (4)
C5	0.18144 (12)	0.22937 (15)	0.0425 (2)	0.0263 (4)
H5A	0.1322	0.2204	−0.0486	0.032*
C6	0.22639 (12)	0.13762 (14)	0.1156 (2)	0.0250 (4)
C7	0.50721 (11)	0.23467 (15)	0.6408 (2)	0.0246 (4)
C8	0.57746 (12)	0.18910 (16)	0.7620 (2)	0.0297 (4)
H8A	0.5866	0.1128	0.7720	0.036*
C9	0.63115 (12)	0.26085 (17)	0.8633 (2)	0.0313 (4)
H9A	0.6789	0.2335	0.9463	0.038*
C10	0.61819 (12)	0.37458 (16)	0.8491 (2)	0.0317 (4)
H10A	0.6575	0.4209	0.9230	0.038*
C11	0.55176 (13)	0.41972 (16)	0.7340 (2)	0.0300 (4)
H11A	0.5440	0.4963	0.7256	0.036*
C12	0.49490 (12)	0.34845 (15)	0.6274 (2)	0.0250 (4)
C13	0.15659 (13)	0.43184 (15)	0.0165 (2)	0.0324 (4)
H13A	0.1404	0.4780	0.0983	0.049*
H13B	0.1033	0.4080	−0.0636	0.049*
H13C	0.1938	0.4732	−0.0385	0.049*
C14	0.20102 (12)	0.02858 (15)	0.0498 (2)	0.0266 (4)
H14A	0.2401	−0.0302	0.0872	0.032*
C15	0.11424 (13)	−0.09878 (15)	−0.1139 (2)	0.0289 (4)
C16	0.17777 (13)	−0.15712 (16)	−0.1667 (2)	0.0326 (4)
H16A	0.2324	−0.1241	−0.1664	0.039*
C17	0.16105 (14)	−0.26315 (17)	−0.2193 (3)	0.0372 (5)
H17A	0.2043	−0.3025	−0.2561	0.045*
C18	0.08242 (14)	−0.31249 (17)	−0.2191 (3)	0.0372 (5)
H18A	0.0722	−0.3862	−0.2520	0.045*
C19	0.01889 (14)	−0.25433 (17)	−0.1710 (3)	0.0362 (5)
H19A	−0.0356	−0.2880	−0.1720	0.043*
C20	0.03324 (13)	−0.14724 (17)	−0.1210 (2)	0.0339 (4)
H20A	−0.0119	−0.1070	−0.0917	0.041*

	U11	U22	U33	U12	U13	U23
O	0.0304 (7)	0.0216 (6)	0.0312 (7)	0.0013 (5)	0.0055 (6)	0.0000 (5)
N1	0.0262 (7)	0.0248 (8)	0.0290 (8)	0.0020 (6)	0.0101 (6)	−0.0001 (6)
N2	0.0269 (7)	0.0220 (7)	0.0255 (8)	−0.0012 (6)	0.0126 (6)	−0.0005 (6)
N3	0.0296 (8)	0.0222 (7)	0.0279 (8)	−0.0019 (6)	0.0104 (6)	−0.0011 (6)
N4	0.0343 (8)	0.0260 (8)	0.0299 (9)	0.0017 (7)	0.0084 (7)	−0.0004 (7)
C1	0.0263 (8)	0.0217 (8)	0.0272 (9)	0.0018 (7)	0.0149 (7)	0.0012 (7)
C2	0.0241 (8)	0.0243 (9)	0.0256 (9)	0.0001 (7)	0.0123 (7)	0.0005 (7)
C3	0.0297 (9)	0.0207 (8)	0.0300 (10)	−0.0001 (7)	0.0149 (8)	−0.0006 (7)
C4	0.0299 (9)	0.0235 (9)	0.0296 (10)	0.0045 (7)	0.0158 (8)	0.0031 (7)
C5	0.0267 (8)	0.0276 (9)	0.0266 (9)	0.0006 (7)	0.0105 (7)	0.0003 (7)
C6	0.0282 (9)	0.0230 (9)	0.0286 (9)	−0.0001 (7)	0.0157 (8)	−0.0002 (7)
C7	0.0257 (8)	0.0254 (9)	0.0266 (9)	−0.0022 (7)	0.0138 (7)	−0.0032 (7)
C8	0.0328 (9)	0.0253 (9)	0.0338 (10)	0.0040 (8)	0.0136 (8)	0.0013 (8)
C9	0.0261 (9)	0.0394 (11)	0.0289 (10)	0.0031 (8)	0.0080 (8)	0.0023 (8)
C10	0.0308 (9)	0.0351 (10)	0.0316 (10)	−0.0087 (8)	0.0123 (8)	−0.0055 (8)
C11	0.0344 (10)	0.0253 (9)	0.0336 (10)	−0.0037 (8)	0.0144 (8)	−0.0017 (8)
C12	0.0267 (8)	0.0260 (9)	0.0261 (9)	0.0008 (7)	0.0138 (7)	0.0026 (7)
C13	0.0345 (10)	0.0262 (9)	0.0356 (11)	0.0042 (8)	0.0070 (8)	0.0029 (8)
C14	0.0301 (9)	0.0231 (9)	0.0288 (10)	0.0014 (7)	0.0115 (8)	0.0003 (7)
C15	0.0354 (10)	0.0258 (9)	0.0231 (9)	0.0009 (8)	0.0032 (8)	0.0013 (7)
C16	0.0301 (9)	0.0352 (10)	0.0317 (10)	−0.0023 (8)	0.0064 (8)	−0.0003 (9)
C17	0.0395 (11)	0.0364 (11)	0.0363 (11)	0.0050 (9)	0.0108 (9)	−0.0071 (9)
C18	0.0468 (12)	0.0299 (10)	0.0323 (11)	−0.0038 (9)	0.0055 (9)	−0.0045 (9)
C19	0.0354 (10)	0.0382 (11)	0.0335 (11)	−0.0092 (9)	0.0059 (9)	−0.0025 (9)
C20	0.0303 (10)	0.0380 (11)	0.0332 (10)	0.0018 (8)	0.0076 (8)	−0.0027 (9)

O—C1	1.352 (2)	C8—H8A	0.9500
O—H0A	0.8400	C9—C10	1.414 (3)
N1—N2	1.338 (2)	C9—H9A	0.9500
N1—C7	1.348 (2)	C10—C11	1.354 (3)
N2—N3	1.331 (2)	C10—H10A	0.9500
N2—C2	1.427 (2)	C11—C12	1.404 (3)
N3—C12	1.358 (2)	C11—H11A	0.9500
N4—C14	1.260 (2)	C13—H13A	0.9800
N4—C15	1.426 (2)	C13—H13B	0.9800
C1—C6	1.404 (3)	C13—H13C	0.9800
C1—C2	1.405 (2)	C14—H14A	0.9500
C2—C3	1.392 (2)	C15—C20	1.394 (3)
C3—C4	1.386 (3)	C15—C16	1.394 (3)
C3—H3B	0.9500	C16—C17	1.382 (3)
C4—C5	1.393 (2)	C16—H16A	0.9500
C4—C13	1.506 (2)	C17—C18	1.378 (3)
C5—C6	1.391 (2)	C17—H17A	0.9500
C5—H5A	0.9500	C18—C19	1.373 (3)
C6—C14	1.468 (2)	C18—H18A	0.9500
C7—C12	1.413 (3)	C19—C20	1.385 (3)
C7—C8	1.418 (3)	C19—H19A	0.9500
C8—C9	1.364 (3)	C20—H20A	0.9500
C1—O—H0A	109.5	C11—C10—H10A	118.8
N2—N1—C7	103.56 (15)	C9—C10—H10A	118.8
N3—N2—N1	116.36 (14)	C10—C11—C12	117.10 (18)
N3—N2—C2	121.88 (14)	C10—C11—H11A	121.4
N1—N2—C2	121.76 (14)	C12—C11—H11A	121.4
N2—N3—C12	103.27 (14)	N3—C12—C11	130.60 (17)
C14—N4—C15	117.45 (16)	N3—C12—C7	108.41 (16)
O—C1—C6	118.06 (16)	C11—C12—C7	120.98 (18)
O—C1—C2	123.58 (16)	C4—C13—H13A	109.5
C6—C1—C2	118.35 (16)	C4—C13—H13B	109.5
C3—C2—C1	120.56 (17)	H13A—C13—H13B	109.5
C3—C2—N2	119.07 (16)	C4—C13—H13C	109.5
C1—C2—N2	120.37 (15)	H13A—C13—H13C	109.5
C4—C3—C2	121.34 (17)	H13B—C13—H13C	109.5
C4—C3—H3B	119.3	N4—C14—C6	122.78 (17)
C2—C3—H3B	119.3	N4—C14—H14A	118.6
C3—C4—C5	117.88 (16)	C6—C14—H14A	118.6
C3—C4—C13	121.25 (17)	C20—C15—C16	119.25 (18)
C5—C4—C13	120.86 (17)	C20—C15—N4	118.99 (17)
C6—C5—C4	122.06 (17)	C16—C15—N4	121.76 (17)
C6—C5—H5A	119.0	C17—C16—C15	119.81 (19)
C4—C5—H5A	119.0	C17—C16—H16A	120.1
C5—C6—C1	119.80 (16)	C15—C16—H16A	120.1
C5—C6—C14	120.93 (17)	C18—C17—C16	120.77 (19)
C1—C6—C14	119.24 (16)	C18—C17—H17A	119.6
N1—C7—C12	108.40 (16)	C16—C17—H17A	119.6
N1—C7—C8	130.60 (17)	C19—C18—C17	119.52 (19)
C12—C7—C8	121.00 (17)	C19—C18—H18A	120.2
C9—C8—C7	116.32 (18)	C17—C18—H18A	120.2
C9—C8—H8A	121.8	C18—C19—C20	120.85 (19)
C7—C8—H8A	121.8	C18—C19—H19A	119.6
C8—C9—C10	122.26 (19)	C20—C19—H19A	119.6
C8—C9—H9A	118.9	C19—C20—C15	119.70 (19)
C10—C9—H9A	118.9	C19—C20—H20A	120.1
C11—C10—C9	122.34 (19)	C15—C20—H20A	120.1
C7—N1—N2—N3	−0.34 (18)	N1—C7—C8—C9	179.37 (18)
C7—N1—N2—C2	178.92 (14)	C12—C7—C8—C9	0.3 (2)
N1—N2—N3—C12	0.31 (18)	C7—C8—C9—C10	−0.2 (3)
C2—N2—N3—C12	−178.95 (14)	C8—C9—C10—C11	−0.1 (3)
O—C1—C2—C3	−178.92 (15)	C9—C10—C11—C12	0.2 (3)
C6—C1—C2—C3	0.4 (2)	N2—N3—C12—C11	179.15 (18)
O—C1—C2—N2	0.7 (2)	N2—N3—C12—C7	−0.15 (18)
C6—C1—C2—N2	−179.96 (15)	C10—C11—C12—N3	−179.33 (17)
N3—N2—C2—C3	−0.9 (2)	C10—C11—C12—C7	−0.1 (3)
N1—N2—C2—C3	179.87 (15)	N1—C7—C12—N3	−0.04 (19)
N3—N2—C2—C1	179.46 (15)	C8—C7—C12—N3	179.22 (15)
N1—N2—C2—C1	0.2 (2)	N1—C7—C12—C11	−179.42 (15)
C1—C2—C3—C4	0.3 (3)	C8—C7—C12—C11	−0.2 (3)
N2—C2—C3—C4	−179.37 (15)	C15—N4—C14—C6	177.26 (16)
C2—C3—C4—C5	−0.6 (3)	C5—C6—C14—N4	−13.4 (3)
C2—C3—C4—C13	179.92 (16)	C1—C6—C14—N4	168.64 (17)
C3—C4—C5—C6	0.2 (3)	C14—N4—C15—C20	132.8 (2)
C13—C4—C5—C6	179.72 (16)	C14—N4—C15—C16	−47.7 (3)
C4—C5—C6—C1	0.5 (3)	C20—C15—C16—C17	−2.4 (3)
C4—C5—C6—C14	−177.48 (16)	N4—C15—C16—C17	178.13 (18)
O—C1—C6—C5	178.60 (15)	C15—C16—C17—C18	−0.6 (3)
C2—C1—C6—C5	−0.8 (2)	C16—C17—C18—C19	2.2 (3)
O—C1—C6—C14	−3.4 (2)	C17—C18—C19—C20	−0.7 (3)
C2—C1—C6—C14	177.22 (15)	C18—C19—C20—C15	−2.2 (3)
N2—N1—C7—C12	0.21 (17)	C16—C15—C20—C19	3.8 (3)
N2—N1—C7—C8	−178.95 (17)	N4—C15—C20—C19	−176.73 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O—H0A···N1	0.84	1.85	2.591 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O—H0A⋯N1	0.84	1.85	2.591 (2)	146