1-(1H-1,2,3-Benzotriazol-1-yl)-2-(4-meth-oxy-phen-yl)ethanone.

In the title compound, C(15)H(13)N(3)O(2), the dihedral angle between the benzotriazole ring system (r.m.s. deviation = 0.0124 Å) and the benzene ring is 76.21 (3)°. The meth-oxy C atom deviates from its benzene ring plane by 0.063 (2)Å. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds generate R(2) (2)(12) loops.

Related literature

For chemical background, see: Katritzky et al. (1996a ▶,b ▶, 2005 ▶, 2010 ▶). For a related structure, see: Selvarathy Grace et al. (2012 ▶). For related literature, see: Zou et al. (2006 ▶).

Experimental

Crystal data

C15H13N3O2

M = 267.28

Monoclinic,

a = 5.4209 (1) Å

b = 24.4894 (5) Å

c = 10.0555 (2) Å

β = 98.552 (2)°

V = 1320.07 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.75 mm−1

T = 296 K

0.34 × 0.17 × 0.16 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas CCD) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.784, T max = 0.889

6122 measured reflections

2707 independent reflections

2340 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.08

2707 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and X-SEED (Barbour, 2001 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812043759/hb6975sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043759/hb6975Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043759/hb6975Isup3.cml

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

C15H13N3O2	F(000) = 560
Mr = 267.28	Dx = 1.345 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 3661 reflections
a = 5.4209 (1) Å	θ = 4.4–76.0°
b = 24.4894 (5) Å	µ = 0.75 mm−1
c = 10.0555 (2) Å	T = 296 K
β = 98.552 (2)°	Prismatic, colorless
V = 1320.07 (4) Å3	0.34 × 0.17 × 0.16 mm
Z = 4

Agilent SuperNova (Dual, Cu at zero, Atlas CCD) diffractometer	2707 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2340 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.019
ω scans	θmax = 76.2°, θmin = 4.8°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −6→4
Tmin = 0.784, Tmax = 0.889	k = −29→30
6122 measured reflections	l = −12→12

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0527P)2 + 0.1534P] where P = (Fo2 + 2Fc2)/3
2707 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.16 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
O1	0.2197 (2)	0.47488 (5)	0.37631 (10)	0.0750 (3)
O2	0.5718 (2)	0.24790 (4)	0.49538 (12)	0.0737 (3)
N1	0.17264 (19)	0.52715 (4)	0.19212 (9)	0.0463 (2)
N2	0.2345 (2)	0.54066 (5)	0.06808 (11)	0.0581 (3)
N3	0.1096 (2)	0.58305 (5)	0.02364 (12)	0.0640 (3)
C1	−0.0418 (2)	0.59893 (5)	0.11725 (13)	0.0517 (3)
C2	−0.2135 (3)	0.64152 (6)	0.11304 (15)	0.0647 (4)
H2	−0.2396	0.6657	0.0410	0.078*
C3	−0.3418 (3)	0.64602 (7)	0.21992 (16)	0.0680 (4)
H3	−0.4572	0.6741	0.2207	0.082*
C4	−0.3036 (3)	0.60952 (6)	0.32785 (15)	0.0639 (4)
H4	−0.3955	0.6139	0.3982	0.077*
C5	−0.1351 (3)	0.56739 (6)	0.33368 (13)	0.0538 (3)
H5	−0.1104	0.5431	0.4056	0.065*
C6	−0.0036 (2)	0.56326 (5)	0.22524 (11)	0.0445 (3)
C7	0.2792 (2)	0.48237 (5)	0.26753 (12)	0.0482 (3)
C8	0.4576 (2)	0.44711 (5)	0.20553 (13)	0.0522 (3)
H8A	0.6154	0.4661	0.2081	0.063*
H8B	0.3910	0.4401	0.1122	0.063*
C9	0.5001 (2)	0.39358 (5)	0.28009 (12)	0.0463 (3)
C10	0.7140 (2)	0.38340 (6)	0.36909 (14)	0.0553 (3)
H10	0.8398	0.4096	0.3802	0.066*
C11	0.7477 (2)	0.33526 (6)	0.44275 (14)	0.0559 (3)
H11	0.8941	0.3294	0.5020	0.067*
C12	0.5628 (2)	0.29645 (5)	0.42717 (13)	0.0501 (3)
C13	0.3460 (2)	0.30573 (6)	0.33780 (14)	0.0548 (3)
H13	0.2207	0.2795	0.3265	0.066*
C14	0.3161 (2)	0.35371 (5)	0.26571 (13)	0.0515 (3)
H14	0.1698	0.3595	0.2063	0.062*
C15	0.7849 (3)	0.23650 (8)	0.59061 (19)	0.0839 (5)
H15A	0.9308	0.2370	0.5469	0.126*
H15B	0.7676	0.2011	0.6293	0.126*
H15C	0.8010	0.2637	0.6602	0.126*

	U11	U22	U33	U12	U13	U23
O1	0.1114 (9)	0.0677 (7)	0.0547 (6)	0.0257 (6)	0.0415 (6)	0.0192 (5)
O2	0.0810 (7)	0.0529 (6)	0.0814 (7)	−0.0002 (5)	−0.0071 (6)	0.0172 (5)
N1	0.0552 (5)	0.0463 (5)	0.0402 (5)	−0.0011 (4)	0.0166 (4)	0.0041 (4)
N2	0.0705 (7)	0.0606 (7)	0.0485 (6)	0.0056 (5)	0.0264 (5)	0.0127 (5)
N3	0.0781 (8)	0.0648 (7)	0.0534 (6)	0.0118 (6)	0.0244 (6)	0.0174 (5)
C1	0.0591 (7)	0.0498 (7)	0.0473 (6)	−0.0008 (5)	0.0118 (5)	0.0039 (5)
C2	0.0755 (9)	0.0577 (8)	0.0610 (8)	0.0103 (7)	0.0102 (7)	0.0080 (7)
C3	0.0720 (9)	0.0591 (9)	0.0735 (10)	0.0127 (7)	0.0128 (7)	−0.0067 (7)
C4	0.0719 (9)	0.0647 (9)	0.0591 (8)	0.0034 (7)	0.0230 (7)	−0.0109 (7)
C5	0.0671 (8)	0.0536 (7)	0.0432 (6)	−0.0022 (6)	0.0168 (6)	−0.0032 (5)
C6	0.0509 (6)	0.0425 (6)	0.0409 (6)	−0.0059 (5)	0.0092 (5)	−0.0029 (5)
C7	0.0583 (7)	0.0450 (6)	0.0438 (6)	−0.0031 (5)	0.0160 (5)	0.0044 (5)
C8	0.0561 (7)	0.0517 (7)	0.0525 (7)	−0.0008 (5)	0.0203 (5)	0.0058 (5)
C9	0.0460 (6)	0.0478 (6)	0.0475 (6)	0.0016 (5)	0.0149 (5)	0.0007 (5)
C10	0.0427 (6)	0.0570 (8)	0.0664 (8)	−0.0075 (5)	0.0089 (5)	0.0013 (6)
C11	0.0431 (6)	0.0616 (8)	0.0608 (8)	0.0038 (5)	0.0007 (5)	0.0016 (6)
C12	0.0540 (6)	0.0449 (6)	0.0513 (7)	0.0041 (5)	0.0075 (5)	−0.0001 (5)
C13	0.0527 (7)	0.0493 (7)	0.0603 (7)	−0.0088 (5)	0.0008 (6)	0.0007 (6)
C14	0.0473 (6)	0.0539 (7)	0.0514 (6)	−0.0020 (5)	0.0011 (5)	0.0014 (5)
C15	0.0787 (10)	0.0842 (12)	0.0863 (11)	0.0217 (9)	0.0046 (9)	0.0308 (10)

O1—C7	1.1997 (14)	C7—C8	1.4997 (18)
O2—C12	1.3700 (16)	C8—C9	1.5106 (17)
O2—C15	1.414 (2)	C8—H8A	0.9700
N1—C6	1.3785 (16)	C8—H8B	0.9700
N1—N2	1.3792 (13)	C9—C10	1.3783 (18)
N1—C7	1.4075 (16)	C9—C14	1.3879 (17)
N2—N3	1.2829 (16)	C10—C11	1.3898 (19)
N3—C1	1.3928 (17)	C10—H10	0.9300
C1—C6	1.3849 (17)	C11—C12	1.3732 (18)
C1—C2	1.394 (2)	C11—H11	0.9300
C2—C3	1.368 (2)	C12—C13	1.3878 (18)
C2—H2	0.9300	C13—C14	1.3775 (18)
C3—C4	1.398 (2)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.373 (2)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.3924 (17)	C15—H15C	0.9600
C5—H5	0.9300
C12—O2—C15	118.34 (13)	C9—C8—H8A	109.5
C6—N1—N2	109.58 (10)	C7—C8—H8B	109.5
C6—N1—C7	127.83 (10)	C9—C8—H8B	109.5
N2—N1—C7	122.59 (10)	H8A—C8—H8B	108.1
N3—N2—N1	108.80 (10)	C10—C9—C14	117.56 (12)
N2—N3—C1	108.91 (10)	C10—C9—C8	122.04 (11)
C6—C1—N3	108.63 (11)	C14—C9—C8	120.32 (11)
C6—C1—C2	121.12 (12)	C9—C10—C11	122.05 (12)
N3—C1—C2	130.24 (12)	C9—C10—H10	119.0
C3—C2—C1	116.83 (13)	C11—C10—H10	119.0
C3—C2—H2	121.6	C12—C11—C10	119.37 (12)
C1—C2—H2	121.6	C12—C11—H11	120.3
C2—C3—C4	121.63 (14)	C10—C11—H11	120.3
C2—C3—H3	119.2	O2—C12—C11	124.94 (12)
C4—C3—H3	119.2	O2—C12—C13	115.46 (12)
C5—C4—C3	122.31 (13)	C11—C12—C13	119.60 (12)
C5—C4—H4	118.8	C14—C13—C12	120.17 (12)
C3—C4—H4	118.8	C14—C13—H13	119.9
C4—C5—C6	115.84 (13)	C12—C13—H13	119.9
C4—C5—H5	122.1	C13—C14—C9	121.25 (12)
C6—C5—H5	122.1	C13—C14—H14	119.4
N1—C6—C1	104.08 (10)	C9—C14—H14	119.4
N1—C6—C5	133.61 (12)	O2—C15—H15A	109.5
C1—C6—C5	122.28 (12)	O2—C15—H15B	109.5
O1—C7—N1	117.76 (11)	H15A—C15—H15B	109.5
O1—C7—C8	124.65 (12)	O2—C15—H15C	109.5
N1—C7—C8	117.59 (10)	H15A—C15—H15C	109.5
C7—C8—C9	110.69 (10)	H15B—C15—H15C	109.5
C7—C8—H8A	109.5
C6—N1—N2—N3	0.65 (15)	C6—N1—C7—O1	−2.9 (2)
C7—N1—N2—N3	−179.84 (12)	N2—N1—C7—O1	177.64 (13)
N1—N2—N3—C1	−0.39 (16)	C6—N1—C7—C8	176.55 (11)
N2—N3—C1—C6	0.00 (16)	N2—N1—C7—C8	−2.87 (17)
N2—N3—C1—C2	−178.46 (15)	O1—C7—C8—C9	14.73 (19)
C6—C1—C2—C3	−0.3 (2)	N1—C7—C8—C9	−164.72 (11)
N3—C1—C2—C3	178.03 (15)	C7—C8—C9—C10	−103.08 (14)
C1—C2—C3—C4	−0.3 (2)	C7—C8—C9—C14	73.62 (15)
C2—C3—C4—C5	0.4 (3)	C14—C9—C10—C11	−0.1 (2)
C3—C4—C5—C6	0.1 (2)	C8—C9—C10—C11	176.70 (12)
N2—N1—C6—C1	−0.62 (13)	C9—C10—C11—C12	−0.1 (2)
C7—N1—C6—C1	179.91 (12)	C15—O2—C12—C11	0.8 (2)
N2—N1—C6—C5	177.24 (13)	C15—O2—C12—C13	−178.41 (14)
C7—N1—C6—C5	−2.2 (2)	C10—C11—C12—O2	−178.87 (13)
N3—C1—C6—N1	0.38 (14)	C10—C11—C12—C13	0.3 (2)
C2—C1—C6—N1	179.01 (13)	O2—C12—C13—C14	178.92 (12)
N3—C1—C6—C5	−177.78 (12)	C11—C12—C13—C14	−0.3 (2)
C2—C1—C6—C5	0.8 (2)	C12—C13—C14—C9	0.1 (2)
C4—C5—C6—N1	−178.29 (13)	C10—C9—C14—C13	0.06 (19)
C4—C5—C6—C1	−0.75 (19)	C8—C9—C14—C13	−176.78 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1i	0.93	2.40	3.1912 (16)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.93	2.40	3.1912 (16)	143

Symmetry code: (i) .