3-(1H-Benzotriazol-1-yl)-1-(3-methoxy-phen-yl)propan-1-one.

In the title mol-ecule, C(16)H(15)N(3)O(2), the benzotriazole fragment and the benzene ring form a dihedral angle of 75.02 (1)°. In the crystal structure, mol-ecules related by translation along the a axis are linked into chains via weak C-H⋯π inter-actions.

Related literature

For the pharmacological activity of 1H-benzotriazole derivatives, see: Chen & Wu (2005 ▶). Some details of the synthesis have been described by Zhu et al. (2007 ▶). For reference values of geometric parameters in organic mol­ecules, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H15N3O2

M = 281.31

Monoclinic,

a = 5.3583 (14) Å

b = 12.976 (4) Å

c = 19.688 (5) Å

β = 91.146 (4)°

V = 1368.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.21 × 0.15 × 0.07 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.994

7461 measured reflections

2693 independent reflections

2279 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.112

S = 1.04

2693 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004127/cv2510sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004127/cv2510Isup2.hkl

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

C16H15N3O2	F(000) = 592
Mr = 281.31	Dx = 1.365 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.3583 (14) Å	Cell parameters from 3062 reflections
b = 12.976 (4) Å	θ = 2.6–25.9°
c = 19.688 (5) Å	µ = 0.09 mm−1
β = 91.146 (4)°	T = 293 K
V = 1368.6 (6) Å3	Block, colourless
Z = 4	0.21 × 0.15 × 0.07 mm

Siemens SMART 1000 CCD area-detector diffractometer	2693 independent reflections
Radiation source: fine-focus sealed tube	2279 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 8.33 pixels mm-1	θmax = 26.0°, θmin = 1.9°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −16→16
Tmin = 0.981, Tmax = 0.994	l = −24→17
7461 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.249P] where P = (Fo2 + 2Fc2)/3
2693 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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
O1	0.2340 (2)	0.48618 (9)	0.09618 (6)	0.0607 (3)
O2	−0.2250 (2)	0.87656 (8)	−0.00231 (6)	0.0570 (3)
N1	0.0340 (2)	0.44726 (9)	0.23515 (6)	0.0427 (3)
C6	0.1036 (2)	0.64278 (10)	0.04534 (6)	0.0396 (3)
C2	−0.0452 (3)	0.80221 (11)	−0.00439 (7)	0.0444 (3)
C1	−0.0680 (3)	0.72307 (11)	0.04300 (7)	0.0428 (3)
H1A	−0.1990	0.7240	0.0733	0.051*
C10	0.2033 (2)	0.37083 (10)	0.24527 (7)	0.0390 (3)
C7	0.0797 (2)	0.55465 (11)	0.09372 (7)	0.0415 (3)
C5	0.3012 (3)	0.64292 (12)	0.00019 (7)	0.0462 (3)
H5A	0.4176	0.5898	0.0012	0.055*
C8	−0.1429 (3)	0.55249 (11)	0.13963 (7)	0.0458 (3)
H8A	−0.2938	0.5586	0.1119	0.055*
H8B	−0.1348	0.6120	0.1694	0.055*
N2	0.0569 (3)	0.51863 (10)	0.28486 (7)	0.0573 (4)
C12	0.5305 (3)	0.33871 (12)	0.32934 (8)	0.0541 (4)
H12A	0.6189	0.3565	0.3687	0.065*
C13	0.5867 (3)	0.25211 (13)	0.29353 (8)	0.0579 (4)
H13A	0.7178	0.2106	0.3087	0.070*
N3	0.2374 (3)	0.49148 (10)	0.32671 (7)	0.0589 (4)
C3	0.1519 (3)	0.80179 (12)	−0.04920 (7)	0.0498 (4)
H3B	0.1684	0.8543	−0.0810	0.060*
C11	0.3340 (3)	0.39961 (11)	0.30415 (7)	0.0440 (3)
C15	0.2589 (3)	0.28109 (11)	0.20939 (8)	0.0505 (4)
H15A	0.1686	0.2617	0.1706	0.061*
C4	0.3230 (3)	0.72214 (13)	−0.04583 (7)	0.0518 (4)
H4A	0.4562	0.7221	−0.0754	0.062*
C9	−0.1613 (3)	0.45603 (12)	0.18278 (8)	0.0516 (4)
H9A	−0.3224	0.4553	0.2044	0.062*
H9B	−0.1536	0.3962	0.1533	0.062*
C14	0.4524 (3)	0.22363 (12)	0.23434 (9)	0.0590 (4)
H14A	0.4972	0.1638	0.2116	0.071*
C16	−0.2412 (4)	0.94720 (13)	−0.05808 (9)	0.0621 (4)
H16A	−0.3743	0.9952	−0.0507	0.093*
H16B	−0.2738	0.9098	−0.0994	0.093*
H16C	−0.0865	0.9839	−0.0616	0.093*

	U11	U22	U33	U12	U13	U23
O1	0.0544 (6)	0.0619 (7)	0.0661 (7)	0.0170 (5)	0.0131 (5)	0.0130 (5)
O2	0.0617 (7)	0.0522 (6)	0.0572 (7)	0.0079 (5)	0.0049 (5)	0.0124 (5)
N1	0.0441 (6)	0.0438 (6)	0.0404 (6)	−0.0021 (5)	0.0016 (5)	0.0031 (5)
C6	0.0367 (7)	0.0471 (7)	0.0348 (7)	−0.0026 (6)	−0.0028 (5)	−0.0029 (5)
C2	0.0446 (8)	0.0454 (8)	0.0430 (8)	−0.0040 (6)	−0.0049 (6)	0.0004 (6)
C1	0.0406 (7)	0.0493 (8)	0.0386 (7)	−0.0021 (6)	0.0024 (6)	0.0005 (6)
C10	0.0389 (7)	0.0402 (7)	0.0381 (7)	−0.0062 (5)	0.0051 (5)	0.0047 (5)
C7	0.0368 (7)	0.0471 (8)	0.0405 (7)	0.0005 (6)	−0.0024 (5)	−0.0024 (6)
C5	0.0394 (7)	0.0570 (8)	0.0423 (8)	0.0010 (6)	0.0016 (6)	−0.0028 (6)
C8	0.0358 (7)	0.0545 (8)	0.0471 (8)	0.0020 (6)	0.0005 (6)	0.0077 (6)
N2	0.0683 (9)	0.0498 (7)	0.0537 (8)	0.0062 (6)	0.0001 (7)	−0.0052 (6)
C12	0.0559 (9)	0.0585 (9)	0.0476 (9)	−0.0050 (7)	−0.0089 (7)	0.0084 (7)
C13	0.0536 (9)	0.0557 (9)	0.0644 (10)	0.0074 (7)	−0.0007 (8)	0.0161 (8)
N3	0.0747 (9)	0.0522 (8)	0.0493 (8)	0.0034 (7)	−0.0080 (7)	−0.0087 (6)
C3	0.0522 (9)	0.0562 (9)	0.0409 (8)	−0.0107 (7)	−0.0002 (6)	0.0070 (6)
C11	0.0497 (8)	0.0437 (7)	0.0387 (7)	−0.0074 (6)	0.0006 (6)	0.0021 (6)
C15	0.0588 (9)	0.0473 (8)	0.0453 (8)	−0.0034 (7)	−0.0015 (7)	−0.0053 (6)
C4	0.0453 (8)	0.0683 (10)	0.0420 (8)	−0.0070 (7)	0.0079 (6)	0.0004 (7)
C9	0.0385 (8)	0.0610 (9)	0.0552 (9)	−0.0070 (7)	−0.0021 (6)	0.0119 (7)
C14	0.0703 (11)	0.0457 (8)	0.0613 (10)	0.0074 (8)	0.0072 (8)	−0.0018 (7)
C16	0.0732 (11)	0.0537 (9)	0.0591 (10)	0.0047 (8)	−0.0062 (8)	0.0119 (8)

O1—C7	1.2137 (17)	C8—H8B	0.9700
O2—C2	1.3649 (18)	N2—N3	1.3063 (19)
O2—C16	1.4316 (18)	C12—C13	1.363 (2)
N1—N2	1.3511 (17)	C12—C11	1.399 (2)
N1—C10	1.3563 (17)	C12—H12A	0.9300
N1—C9	1.4586 (18)	C13—C14	1.407 (2)
C6—C1	1.3896 (19)	C13—H13A	0.9300
C6—C5	1.3961 (19)	N3—C11	1.3769 (19)
C6—C7	1.4954 (19)	C3—C4	1.382 (2)
C2—C3	1.389 (2)	C3—H3B	0.9300
C2—C1	1.394 (2)	C15—C14	1.361 (2)
C1—H1A	0.9300	C15—H15A	0.9300
C10—C11	1.3933 (19)	C4—H4A	0.9300
C10—C15	1.397 (2)	C9—H9A	0.9700
C7—C8	1.511 (2)	C9—H9B	0.9700
C5—C4	1.377 (2)	C14—H14A	0.9300
C5—H5A	0.9300	C16—H16A	0.9600
C8—C9	1.517 (2)	C16—H16B	0.9600
C8—H8A	0.9700	C16—H16C	0.9600
C2—O2—C16	117.48 (12)	C12—C13—C14	122.05 (15)
N2—N1—C10	110.12 (12)	C12—C13—H13A	119.0
N2—N1—C9	120.80 (12)	C14—C13—H13A	119.0
C10—N1—C9	128.99 (12)	N2—N3—C11	107.97 (12)
C1—C6—C5	119.18 (13)	C4—C3—C2	118.97 (13)
C1—C6—C7	121.97 (12)	C4—C3—H3B	120.5
C5—C6—C7	118.83 (12)	C2—C3—H3B	120.5
O2—C2—C3	124.61 (13)	N3—C11—C10	108.32 (13)
O2—C2—C1	115.41 (13)	N3—C11—C12	131.29 (14)
C3—C2—C1	119.98 (14)	C10—C11—C12	120.37 (14)
C6—C1—C2	120.50 (13)	C14—C15—C10	116.26 (14)
C6—C1—H1A	119.7	C14—C15—H15A	121.9
C2—C1—H1A	119.7	C10—C15—H15A	121.9
N1—C10—C11	104.48 (12)	C5—C4—C3	121.66 (14)
N1—C10—C15	133.14 (13)	C5—C4—H4A	119.2
C11—C10—C15	122.38 (13)	C3—C4—H4A	119.2
O1—C7—C6	121.22 (12)	N1—C9—C8	113.99 (12)
O1—C7—C8	120.51 (13)	N1—C9—H9A	108.8
C6—C7—C8	118.28 (12)	C8—C9—H9A	108.8
C4—C5—C6	119.69 (14)	N1—C9—H9B	108.8
C4—C5—H5A	120.2	C8—C9—H9B	108.8
C6—C5—H5A	120.2	H9A—C9—H9B	107.7
C7—C8—C9	114.27 (12)	C15—C14—C13	121.90 (15)
C7—C8—H8A	108.7	C15—C14—H14A	119.0
C9—C8—H8A	108.7	C13—C14—H14A	119.0
C7—C8—H8B	108.7	O2—C16—H16A	109.5
C9—C8—H8B	108.7	O2—C16—H16B	109.5
H8A—C8—H8B	107.6	H16A—C16—H16B	109.5
N3—N2—N1	109.11 (12)	O2—C16—H16C	109.5
C13—C12—C11	117.02 (15)	H16A—C16—H16C	109.5
C13—C12—H12A	121.5	H16B—C16—H16C	109.5
C11—C12—H12A	121.5
C16—O2—C2—C3	13.0 (2)	N1—N2—N3—C11	−0.44 (17)
C16—O2—C2—C1	−167.35 (13)	O2—C2—C3—C4	179.60 (13)
C5—C6—C1—C2	0.8 (2)	C1—C2—C3—C4	0.0 (2)
C7—C6—C1—C2	−177.70 (12)	N2—N3—C11—C10	0.20 (17)
O2—C2—C1—C6	179.60 (12)	N2—N3—C11—C12	178.69 (15)
C3—C2—C1—C6	−0.8 (2)	N1—C10—C11—N3	0.12 (15)
N2—N1—C10—C11	−0.40 (14)	C15—C10—C11—N3	179.28 (13)
C9—N1—C10—C11	−176.92 (12)	N1—C10—C11—C12	−178.56 (12)
N2—N1—C10—C15	−179.42 (15)	C15—C10—C11—C12	0.6 (2)
C9—N1—C10—C15	4.1 (2)	C13—C12—C11—N3	−177.86 (15)
C1—C6—C7—O1	−178.41 (13)	C13—C12—C11—C10	0.5 (2)
C5—C6—C7—O1	3.1 (2)	N1—C10—C15—C14	177.59 (14)
C1—C6—C7—C8	1.83 (19)	C11—C10—C15—C14	−1.3 (2)
C5—C6—C7—C8	−176.67 (12)	C6—C5—C4—C3	−0.7 (2)
C1—C6—C5—C4	−0.1 (2)	C2—C3—C4—C5	0.7 (2)
C7—C6—C5—C4	178.46 (13)	N2—N1—C9—C8	61.53 (17)
O1—C7—C8—C9	−4.4 (2)	C10—N1—C9—C8	−122.27 (15)
C6—C7—C8—C9	175.40 (12)	C7—C8—C9—N1	68.40 (17)
C10—N1—N2—N3	0.54 (16)	C10—C15—C14—C13	1.0 (2)
C9—N1—N2—N3	177.39 (12)	C12—C13—C14—C15	0.1 (3)
C11—C12—C13—C14	−0.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···Cg1i	0.97	2.74	3.504	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯Cg1i	0.97	2.74	3.504	136

Symmetry code: (i) . Cg1 is the centroid of atoms C10–C15.