2-(2-Meth-oxy-5-methyl-phen-yl)-2H-benzotriazole.

In the title mol-ecule, C(14)H(13)N(3)O, the dihedral angle between the mean planes of the benzotriazole ring system and the benzene ring is 57.8 (2)°.

Related literature

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

Experimental

Crystal data

C14H13N3O

M = 239.27

Monoclinic,

a = 7.1604 (2) Å

b = 8.2560 (2) Å

c = 11.0342 (3) Å

β = 103.450 (1)°

V = 634.41 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.48 × 0.32 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.962, T max = 0.986

6057 measured reflections

1674 independent reflections

1401 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.136

S = 1.05

1674 reflections

164 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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/S1600536810031363/lh5100sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031363/lh5100Isup2.hkl

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

C14H13N3O	F(000) = 252
Mr = 239.27	Dx = 1.253 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3727 reflections
a = 7.1604 (2) Å	θ = 2.9–28.2°
b = 8.2560 (2) Å	µ = 0.08 mm−1
c = 11.0342 (3) Å	T = 296 K
β = 103.450 (1)°	Columnar, colourless
V = 634.41 (3) Å3	0.48 × 0.32 × 0.17 mm
Z = 2

Bruker APEXII CCD diffractometer	1674 independent reflections
Radiation source: fine-focus sealed tube	1401 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 8.3333 pixels mm-1	θmax = 28.3°, θmin = 1.9°
φ and ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −11→11
Tmin = 0.962, Tmax = 0.986	l = −14→14
6057 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0703P)2 + 0.098P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1674 reflections	Δρmax = 0.17 e Å−3
164 parameters	Δρmin = −0.15 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.067 (13)

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	0.4845 (3)	0.6862 (5)	0.1130 (2)	0.1062 (12)
N1	0.3698 (3)	0.9600 (4)	0.2453 (2)	0.0707 (7)
N2	0.2199 (3)	0.8702 (3)	0.19219 (18)	0.0547 (5)
N3	0.0939 (3)	0.8349 (3)	0.25880 (19)	0.0610 (6)
C1	0.3261 (4)	0.7274 (4)	0.0259 (2)	0.0661 (8)
C2	0.1880 (4)	0.8191 (4)	0.0643 (2)	0.0551 (6)
C3	0.0210 (4)	0.8665 (4)	−0.0174 (2)	0.0563 (6)
H3B	−0.0689	0.9279	0.0113	0.068*
C4	−0.0144 (4)	0.8234 (4)	−0.1425 (2)	0.0602 (7)
C5	0.1215 (5)	0.7297 (4)	−0.1801 (2)	0.0668 (8)
H5A	0.0995	0.6976	−0.2630	0.080*
C6	0.2882 (5)	0.6826 (5)	−0.0987 (3)	0.0720 (8)
H6A	0.3768	0.6198	−0.1274	0.086*
C7	0.3395 (4)	0.9863 (4)	0.3605 (2)	0.0638 (7)
C8	0.4473 (6)	1.0761 (6)	0.4615 (3)	0.0895 (11)
H8A	0.5613	1.1274	0.4574	0.107*
C9	0.3761 (6)	1.0840 (5)	0.5651 (3)	0.0949 (13)
H9A	0.4439	1.1419	0.6336	0.114*
C10	0.2044 (8)	1.0082 (6)	0.5726 (3)	0.1011 (13)
H10A	0.1620	1.0180	0.6458	0.121*
C11	0.0972 (7)	0.9208 (6)	0.4769 (3)	0.0900 (11)
H11A	−0.0172	0.8715	0.4825	0.108*
C12	0.1694 (4)	0.9090 (4)	0.3677 (2)	0.0609 (7)
C13	−0.1948 (5)	0.8824 (5)	−0.2321 (3)	0.0846 (10)
H13A	−0.2701	0.9448	−0.1875	0.127*
H13B	−0.2683	0.7911	−0.2707	0.127*
H13C	−0.1605	0.9487	−0.2951	0.127*
C14	0.6487 (5)	0.6546 (7)	0.0835 (4)	0.0985 (14)
H14A	0.7439	0.6277	0.1575	0.148*
H14B	0.6896	0.7481	0.0448	0.148*
H14C	0.6321	0.5649	0.0266	0.148*

	U11	U22	U33	U12	U13	U23
O	0.0727 (13)	0.190 (4)	0.0590 (11)	0.0505 (19)	0.0224 (10)	0.0159 (18)
N1	0.0598 (13)	0.096 (2)	0.0548 (12)	−0.0144 (13)	0.0095 (10)	−0.0005 (13)
N2	0.0544 (11)	0.0688 (14)	0.0417 (9)	−0.0028 (10)	0.0126 (8)	0.0001 (9)
N3	0.0703 (13)	0.0706 (14)	0.0464 (10)	−0.0090 (12)	0.0222 (9)	−0.0029 (10)
C1	0.0627 (15)	0.089 (2)	0.0502 (13)	0.0096 (16)	0.0203 (11)	0.0099 (14)
C2	0.0568 (13)	0.0702 (16)	0.0403 (10)	−0.0049 (12)	0.0154 (9)	−0.0003 (11)
C3	0.0576 (13)	0.0615 (15)	0.0495 (12)	−0.0047 (12)	0.0122 (10)	−0.0021 (11)
C4	0.0687 (15)	0.0617 (15)	0.0475 (11)	−0.0131 (13)	0.0080 (10)	0.0025 (12)
C5	0.089 (2)	0.0702 (17)	0.0435 (12)	−0.0138 (16)	0.0213 (12)	−0.0059 (12)
C6	0.085 (2)	0.084 (2)	0.0560 (14)	0.0083 (17)	0.0333 (14)	−0.0004 (15)
C7	0.0725 (16)	0.0697 (17)	0.0443 (12)	−0.0040 (14)	0.0037 (11)	0.0046 (12)
C8	0.094 (2)	0.103 (3)	0.0595 (17)	−0.018 (2)	−0.0068 (15)	−0.0009 (19)
C9	0.134 (3)	0.094 (3)	0.0441 (14)	−0.012 (3)	−0.0043 (17)	−0.0044 (16)
C10	0.166 (4)	0.094 (3)	0.0461 (15)	−0.013 (3)	0.0296 (19)	−0.0035 (16)
C11	0.129 (3)	0.094 (2)	0.0549 (16)	−0.021 (2)	0.0374 (18)	−0.0089 (17)
C12	0.0783 (17)	0.0611 (15)	0.0427 (11)	−0.0037 (13)	0.0132 (11)	0.0039 (11)
C13	0.090 (2)	0.095 (3)	0.0565 (15)	−0.009 (2)	−0.0091 (14)	−0.0017 (17)
C14	0.0672 (19)	0.143 (4)	0.091 (2)	0.017 (2)	0.0301 (17)	0.015 (3)

O—C14	1.317 (4)	C7—C12	1.393 (4)
O—C1	1.348 (3)	C7—C8	1.410 (4)
N1—N2	1.324 (3)	C8—C9	1.357 (5)
N1—C7	1.355 (4)	C8—H8A	0.9300
N2—N3	1.322 (3)	C9—C10	1.399 (6)
N2—C2	1.439 (3)	C9—H9A	0.9300
N3—C12	1.345 (3)	C10—C11	1.360 (6)
C1—C2	1.387 (4)	C10—H10A	0.9300
C1—C6	1.389 (4)	C11—C12	1.421 (4)
C2—C3	1.377 (4)	C11—H11A	0.9300
C3—C4	1.391 (4)	C13—H13A	0.9600
C3—H3B	0.9300	C13—H13B	0.9600
C4—C5	1.380 (4)	C13—H13C	0.9600
C4—C13	1.513 (4)	C14—H14A	0.9600
C5—C6	1.372 (4)	C14—H14B	0.9600
C5—H5A	0.9300	C14—H14C	0.9600
C6—H6A	0.9300
C14—O—C1	121.7 (2)	C9—C8—C7	116.6 (4)
N2—N1—C7	102.4 (2)	C9—C8—H8A	121.7
N3—N2—N1	117.7 (2)	C7—C8—H8A	121.7
N3—N2—C2	120.5 (2)	C8—C9—C10	122.5 (3)
N1—N2—C2	121.7 (2)	C8—C9—H9A	118.8
N2—N3—C12	102.2 (2)	C10—C9—H9A	118.8
O—C1—C2	117.5 (2)	C11—C10—C9	122.4 (4)
O—C1—C6	125.2 (3)	C11—C10—H10A	118.8
C2—C1—C6	117.3 (3)	C9—C10—H10A	118.8
C3—C2—C1	121.9 (2)	C10—C11—C12	116.4 (4)
C3—C2—N2	118.3 (2)	C10—C11—H11A	121.8
C1—C2—N2	119.8 (2)	C12—C11—H11A	121.8
C2—C3—C4	120.5 (3)	N3—C12—C7	109.4 (2)
C2—C3—H3B	119.8	N3—C12—C11	129.7 (3)
C4—C3—H3B	119.8	C7—C12—C11	120.8 (3)
C5—C4—C3	117.6 (3)	C4—C13—H13A	109.5
C5—C4—C13	122.6 (3)	C4—C13—H13B	109.5
C3—C4—C13	119.8 (3)	H13A—C13—H13B	109.5
C6—C5—C4	121.9 (2)	C4—C13—H13C	109.5
C6—C5—H5A	119.0	H13A—C13—H13C	109.5
C4—C5—H5A	119.0	H13B—C13—H13C	109.5
C5—C6—C1	120.8 (3)	O—C14—H14A	109.5
C5—C6—H6A	119.6	O—C14—H14B	109.5
C1—C6—H6A	119.6	H14A—C14—H14B	109.5
N1—C7—C12	108.2 (2)	O—C14—H14C	109.5
N1—C7—C8	130.4 (3)	H14A—C14—H14C	109.5
C12—C7—C8	121.4 (3)	H14B—C14—H14C	109.5
C7—N1—N2—N3	0.3 (3)	C13—C4—C5—C6	177.3 (3)
C7—N1—N2—C2	177.1 (3)	C4—C5—C6—C1	0.3 (5)
N1—N2—N3—C12	−0.2 (3)	O—C1—C6—C5	179.4 (3)
C2—N2—N3—C12	−177.0 (2)	C2—C1—C6—C5	0.9 (5)
C14—O—C1—C2	−154.6 (4)	N2—N1—C7—C12	−0.3 (3)
C14—O—C1—C6	26.9 (7)	N2—N1—C7—C8	−178.9 (4)
O—C1—C2—C3	−179.7 (3)	N1—C7—C8—C9	178.0 (4)
C6—C1—C2—C3	−1.0 (5)	C12—C7—C8—C9	−0.4 (5)
O—C1—C2—N2	1.8 (4)	C7—C8—C9—C10	−0.3 (6)
C6—C1—C2—N2	−179.5 (3)	C8—C9—C10—C11	0.3 (7)
N3—N2—C2—C3	56.9 (4)	C9—C10—C11—C12	0.4 (7)
N1—N2—C2—C3	−119.8 (3)	N2—N3—C12—C7	0.0 (3)
N3—N2—C2—C1	−124.6 (3)	N2—N3—C12—C11	177.5 (4)
N1—N2—C2—C1	58.8 (4)	N1—C7—C12—N3	0.2 (4)
C1—C2—C3—C4	−0.1 (4)	C8—C7—C12—N3	178.9 (3)
N2—C2—C3—C4	178.5 (3)	N1—C7—C12—C11	−177.6 (3)
C2—C3—C4—C5	1.2 (4)	C8—C7—C12—C11	1.1 (5)
C2—C3—C4—C13	−177.5 (3)	C10—C11—C12—N3	−178.4 (4)
C3—C4—C5—C6	−1.3 (5)	C10—C11—C12—C7	−1.1 (6)