3-(2H-Benzotriazol-2-yl)-2-hydr-oxy-5-methyl-benzaldehyde.

In the title compound, C(14)H(11)N(3)O(2), the dihedral angle between the mean planes of the benzotriazole ring system and the benzene ring of the salicylaldehyde group is 2.4 (2)°. There is an intra-molecular O-H⋯N hydrogen bond which may influence the mol-ecular conformation.

Related literature

For the application of N,N,O-tridentate Schiff-base metal complexes in the catalytic ring-opening polymerization of l-lactide, see: Wu et al. (2005 ▶); Chen et al. (2006 ▶). For a related structure, see: Li et al. (2009 ▶).

Experimental

Crystal data

C14H11N3O2

M = 253.26

Monoclinic,

a = 12.2724 (5) Å

b = 14.5018 (5) Å

c = 6.8897 (3) Å

β = 91.571 (2)°

V = 1225.71 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.34 × 0.31 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.972, T max = 0.977

13912 measured reflections

2946 independent reflections

1657 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.146

S = 1.01

2946 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 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/S1600536810007233/lh5003sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007233/lh5003Isup2.hkl

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

C14H11N3O2	F(000) = 528
Mr = 253.26	Dx = 1.372 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1657 reflections
a = 12.2724 (5) Å	θ = 1.7–28.3°
b = 14.5018 (5) Å	µ = 0.10 mm−1
c = 6.8897 (3) Å	T = 296 K
β = 91.571 (2)°	Columnar, yellow
V = 1225.71 (8) Å3	0.34 × 0.31 × 0.23 mm
Z = 4

Bruker APEXII CCD diffractometer	2946 independent reflections
Radiation source: fine-focus sealed tube	1657 reflections with I > 2σ(I)
graphite	Rint = 0.070
Detector resolution: 8.3333 pixels mm-1	θmax = 28.3°, θmin = 1.7°
φ and ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −19→19
Tmin = 0.972, Tmax = 0.977	l = −7→9
13912 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.075P)2] where P = (Fo2 + 2Fc2)/3
2946 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Experimental. 1H NMR (CDCl3, ppm): δ 11.88 (s, 1H, PhOH),10.51 (s, 1H, PhCHO), 8.36 (s, 1H, PhH), 7.94 (d, 2H, PhH), 7.68 (s, 1H, PhH), 7.50 (d, 2H, PhH), 2.41 (s, 3H, PhCH3).

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 > 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
O1	0.50858 (9)	0.36518 (6)	0.26655 (17)	0.0578 (3)
H1A	0.5768	0.3681	0.2490	0.069*
O2	0.18809 (10)	0.37151 (8)	0.3322 (2)	0.0816 (4)
N1	0.68476 (10)	0.27325 (8)	0.20289 (19)	0.0488 (3)
N2	0.62690 (10)	0.19539 (8)	0.22480 (18)	0.0458 (3)
N3	0.68234 (10)	0.11695 (8)	0.21302 (19)	0.0517 (4)
C1	0.45880 (12)	0.28244 (9)	0.2757 (2)	0.0435 (4)
C2	0.51319 (12)	0.19766 (9)	0.2580 (2)	0.0428 (4)
C3	0.45656 (12)	0.11543 (10)	0.2707 (2)	0.0471 (4)
H3B	0.4938	0.0600	0.2579	0.057*
C4	0.34523 (12)	0.11386 (10)	0.3022 (2)	0.0490 (4)
C5	0.29195 (12)	0.19740 (10)	0.3180 (2)	0.0493 (4)
H5A	0.2173	0.1977	0.3381	0.059*
C6	0.34674 (12)	0.28099 (10)	0.3048 (2)	0.0456 (4)
C7	0.78649 (11)	0.24258 (10)	0.1756 (2)	0.0476 (4)
C8	0.88414 (13)	0.29132 (12)	0.1448 (2)	0.0578 (5)
H8A	0.8858	0.3554	0.1408	0.069*
C9	0.97489 (13)	0.24055 (13)	0.1215 (2)	0.0637 (5)
H9A	1.0405	0.2706	0.1011	0.076*
C10	0.97342 (14)	0.14307 (13)	0.1272 (3)	0.0672 (5)
H10A	1.0382	0.1111	0.1099	0.081*
C11	0.88075 (13)	0.09447 (12)	0.1571 (2)	0.0622 (5)
H11A	0.8806	0.0304	0.1608	0.075*
C12	0.78537 (12)	0.14584 (11)	0.1820 (2)	0.0491 (4)
C13	0.28498 (14)	0.02373 (11)	0.3176 (3)	0.0687 (5)
H13A	0.2093	0.0356	0.3392	0.103*
H13B	0.3153	−0.0114	0.4241	0.103*
H13C	0.2919	−0.0105	0.1993	0.103*
C14	0.28544 (14)	0.36772 (11)	0.3179 (2)	0.0578 (5)
H14A	0.3241	0.4228	0.3150	0.069*

	U11	U22	U33	U12	U13	U23
O1	0.0533 (6)	0.0414 (6)	0.0792 (9)	−0.0065 (5)	0.0092 (5)	−0.0014 (5)
O2	0.0565 (8)	0.0613 (8)	0.1276 (13)	0.0086 (6)	0.0154 (7)	−0.0057 (7)
N1	0.0475 (7)	0.0449 (7)	0.0540 (9)	−0.0062 (6)	0.0031 (6)	0.0029 (6)
N2	0.0458 (7)	0.0421 (7)	0.0495 (9)	−0.0022 (5)	0.0021 (6)	0.0019 (5)
N3	0.0477 (7)	0.0449 (7)	0.0629 (10)	0.0010 (6)	0.0044 (6)	−0.0005 (6)
C1	0.0505 (9)	0.0395 (7)	0.0405 (9)	−0.0044 (6)	0.0012 (7)	−0.0002 (6)
C2	0.0433 (8)	0.0437 (8)	0.0414 (9)	−0.0004 (6)	0.0013 (6)	0.0014 (6)
C3	0.0482 (9)	0.0399 (8)	0.0532 (10)	0.0018 (6)	0.0012 (7)	0.0019 (6)
C4	0.0491 (9)	0.0438 (8)	0.0542 (11)	−0.0018 (6)	0.0017 (7)	0.0028 (7)
C5	0.0444 (8)	0.0508 (9)	0.0530 (10)	−0.0006 (6)	0.0046 (7)	0.0009 (7)
C6	0.0484 (9)	0.0435 (8)	0.0448 (10)	0.0002 (6)	0.0018 (7)	0.0000 (6)
C7	0.0466 (9)	0.0543 (9)	0.0420 (9)	−0.0041 (7)	0.0025 (7)	−0.0001 (7)
C8	0.0539 (10)	0.0615 (10)	0.0583 (12)	−0.0110 (8)	0.0053 (8)	0.0019 (8)
C9	0.0510 (10)	0.0747 (12)	0.0657 (13)	−0.0113 (9)	0.0071 (8)	0.0008 (9)
C10	0.0478 (9)	0.0776 (12)	0.0766 (14)	0.0042 (9)	0.0070 (8)	−0.0052 (9)
C11	0.0516 (10)	0.0583 (10)	0.0771 (13)	0.0046 (8)	0.0076 (8)	−0.0044 (8)
C12	0.0463 (9)	0.0514 (9)	0.0497 (10)	−0.0021 (7)	0.0021 (7)	−0.0006 (7)
C13	0.0560 (10)	0.0495 (10)	0.1008 (15)	−0.0060 (8)	0.0074 (9)	0.0064 (9)
C14	0.0567 (10)	0.0478 (9)	0.0693 (12)	−0.0005 (7)	0.0078 (8)	−0.0033 (7)

O1—C1	1.3488 (15)	C5—H5A	0.9300
O1—H1A	0.8500	C6—C14	1.470 (2)
O2—C14	1.2026 (18)	C7—C12	1.404 (2)
N1—C7	1.3434 (18)	C7—C8	1.412 (2)
N1—N2	1.3445 (16)	C8—C9	1.348 (2)
N2—N3	1.3292 (16)	C8—H8A	0.9300
N2—C2	1.4206 (18)	C9—C10	1.414 (3)
N3—C12	1.3545 (18)	C9—H9A	0.9300
C1—C6	1.395 (2)	C10—C11	1.358 (2)
C1—C2	1.4058 (19)	C10—H10A	0.9300
C2—C3	1.3842 (18)	C11—C12	1.402 (2)
C3—C4	1.389 (2)	C11—H11A	0.9300
C3—H3B	0.9300	C13—H13A	0.9600
C4—C5	1.3823 (19)	C13—H13B	0.9600
C4—C13	1.507 (2)	C13—H13C	0.9600
C5—C6	1.3905 (19)	C14—H14A	0.9300
C1—O1—H1A	120.0	C12—C7—C8	120.93 (14)
C7—N1—N2	103.50 (12)	C9—C8—C7	116.85 (16)
N3—N2—N1	116.04 (12)	C9—C8—H8A	121.6
N3—N2—C2	122.44 (11)	C7—C8—H8A	121.6
N1—N2—C2	121.52 (11)	C8—C9—C10	122.10 (15)
N2—N3—C12	103.09 (11)	C8—C9—H9A	119.0
O1—C1—C6	118.00 (13)	C10—C9—H9A	119.0
O1—C1—C2	123.87 (13)	C11—C10—C9	122.29 (16)
C6—C1—C2	118.13 (13)	C11—C10—H10A	118.9
C3—C2—C1	120.50 (14)	C9—C10—H10A	118.9
C3—C2—N2	119.17 (12)	C10—C11—C12	116.62 (16)
C1—C2—N2	120.33 (12)	C10—C11—H11A	121.7
C2—C3—C4	121.44 (13)	C12—C11—H11A	121.7
C2—C3—H3B	119.3	N3—C12—C11	129.87 (15)
C4—C3—H3B	119.3	N3—C12—C7	108.91 (12)
C5—C4—C3	117.86 (13)	C11—C12—C7	121.22 (13)
C5—C4—C13	121.36 (14)	C4—C13—H13A	109.5
C3—C4—C13	120.78 (13)	C4—C13—H13B	109.5
C4—C5—C6	121.88 (14)	H13A—C13—H13B	109.5
C4—C5—H5A	119.1	C4—C13—H13C	109.5
C6—C5—H5A	119.1	H13A—C13—H13C	109.5
C5—C6—C1	120.19 (13)	H13B—C13—H13C	109.5
C5—C6—C14	119.52 (14)	O2—C14—C6	123.75 (15)
C1—C6—C14	120.28 (13)	O2—C14—H14A	118.1
N1—C7—C12	108.46 (12)	C6—C14—H14A	118.1
N1—C7—C8	130.62 (15)
C7—N1—N2—N3	−0.35 (17)	C2—C1—C6—C5	0.8 (2)
C7—N1—N2—C2	179.82 (12)	O1—C1—C6—C14	2.1 (2)
N1—N2—N3—C12	0.42 (17)	C2—C1—C6—C14	−178.04 (13)
C2—N2—N3—C12	−179.75 (12)	N2—N1—C7—C12	0.12 (15)
O1—C1—C2—C3	179.41 (13)	N2—N1—C7—C8	−179.78 (15)
C6—C1—C2—C3	−0.5 (2)	N1—C7—C8—C9	−179.89 (14)
O1—C1—C2—N2	−1.3 (2)	C12—C7—C8—C9	0.2 (2)
C6—C1—C2—N2	178.88 (12)	C7—C8—C9—C10	0.1 (2)
N3—N2—C2—C3	−2.7 (2)	C8—C9—C10—C11	−0.2 (3)
N1—N2—C2—C3	177.08 (13)	C9—C10—C11—C12	0.1 (2)
N3—N2—C2—C1	177.91 (13)	N2—N3—C12—C11	−179.89 (15)
N1—N2—C2—C1	−2.3 (2)	N2—N3—C12—C7	−0.30 (16)
C1—C2—C3—C4	−0.4 (3)	C10—C11—C12—N3	179.71 (16)
N2—C2—C3—C4	−179.71 (13)	C10—C11—C12—C7	0.2 (2)
C2—C3—C4—C5	0.8 (2)	N1—C7—C12—N3	0.12 (16)
C2—C3—C4—C13	−179.41 (15)	C8—C7—C12—N3	−179.97 (14)
C3—C4—C5—C6	−0.5 (2)	N1—C7—C12—C11	179.75 (14)
C13—C4—C5—C6	179.77 (14)	C8—C7—C12—C11	−0.3 (2)
C4—C5—C6—C1	−0.4 (3)	C5—C6—C14—O2	−3.1 (3)
C4—C5—C6—C14	178.51 (14)	C1—C6—C14—O2	175.78 (16)
O1—C1—C6—C5	−179.06 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.85	1.94	2.588 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.85	1.94	2.588 (2)	132