4-[3-(2H-Benzotriazol-2-yl)prop-oxy]-3-methoxy-benzaldehyde.

In the title compound, C(17)H(17)N(3)O(3), the 3-methoxy-benzalde-hyde group and the benzotriazole fragment are connected through a flexible oxypropyl chain. The O-C-C-C torsion angle in the central link is -63.9 (2)°, while the plane of the benzene ring of the 3-methoxy-benzaldehyde substituent forms a dihedral angle of 56.4 (4)° with the benzotriazole plane.

Related literature

For general background to the biological activity of 1H-benzotriazole and its derivatives, see: Al-Soud et al. (2003 ▶); Khalafi-Nezhad et al. (2005 ▶); Nanjunda Swamy et al. (2006 ▶). For a related structure, see: Jin et al. (2009 ▶).

Experimental

Crystal data

C17H17N3O3

M = 311.34

Monoclinic,

a = 11.328 (2) Å

b = 8.1278 (16) Å

c = 16.156 (3) Å

β = 100.301 (3)°

V = 1463.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.34 × 0.20 × 0.18 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.967, T max = 0.982

7400 measured reflections

2716 independent reflections

2257 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.111

S = 1.02

2716 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); 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 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810015461/ya2115sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015461/ya2115Isup2.hkl

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

C17H17N3O3	F(000) = 656
Mr = 311.34	Dx = 1.413 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2314 reflections
a = 11.328 (2) Å	θ = 2.4–26.8°
b = 8.1278 (16) Å	µ = 0.10 mm−1
c = 16.156 (3) Å	T = 173 K
β = 100.301 (3)°	Block, colourless
V = 1463.6 (5) Å3	0.34 × 0.20 × 0.18 mm
Z = 4

Bruker SMART diffractometer	2716 independent reflections
Radiation source: fine-focus sealed tube	2257 reflections with I > 2σ(I)
graphite	Rint = 0.030
phi and ω scans	θmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→11
Tmin = 0.967, Tmax = 0.982	k = −9→9
7400 measured reflections	l = −14→19

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0598P)2 + 0.2971P] where P = (Fo2 + 2Fc2)/3
2716 reflections	(Δ/σ)max = 0.002
209 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.23 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 > 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
C1	0.30868 (15)	0.3509 (2)	−0.18483 (10)	0.0304 (4)
H1	0.2604	0.4172	−0.2261	0.036*
C2	0.32240 (13)	0.40484 (19)	−0.09726 (9)	0.0252 (4)
C3	0.38488 (13)	0.30819 (19)	−0.03210 (9)	0.0247 (4)
H3	0.4194	0.2068	−0.0447	0.030*
C4	0.39637 (13)	0.35957 (18)	0.04991 (9)	0.0233 (3)
C5	0.34662 (13)	0.51165 (19)	0.06848 (9)	0.0231 (3)
C6	0.28450 (14)	0.60657 (19)	0.00395 (10)	0.0266 (4)
H6	0.2503	0.7085	0.0161	0.032*
C7	0.27228 (14)	0.5522 (2)	−0.07870 (10)	0.0283 (4)
H7	0.2290	0.6171	−0.1229	0.034*
C8	0.50723 (16)	0.12187 (19)	0.10204 (11)	0.0336 (4)
H8A	0.4451	0.0477	0.0730	0.050*
H8B	0.5457	0.0717	0.1552	0.050*
H8C	0.5675	0.1412	0.0665	0.050*
C9	0.33302 (15)	0.71678 (19)	0.17160 (10)	0.0269 (4)
H9A	0.2451	0.7318	0.1563	0.032*
H9B	0.3725	0.7982	0.1400	0.032*
C10	0.37338 (14)	0.74091 (19)	0.26499 (10)	0.0260 (4)
H10A	0.3584	0.8563	0.2798	0.031*
H10B	0.4607	0.7203	0.2798	0.031*
C11	0.30818 (14)	0.6269 (2)	0.31527 (9)	0.0283 (4)
H11A	0.2212	0.6512	0.3022	0.034*
H11B	0.3198	0.5119	0.2981	0.034*
C12	0.42907 (13)	0.73940 (19)	0.52211 (10)	0.0236 (4)
C13	0.48871 (14)	0.8333 (2)	0.59075 (10)	0.0288 (4)
H13	0.5255	0.9357	0.5829	0.035*
C14	0.49051 (14)	0.7689 (2)	0.66857 (10)	0.0296 (4)
H14	0.5296	0.8285	0.7162	0.036*
C15	0.43636 (14)	0.6163 (2)	0.68129 (10)	0.0305 (4)
H15	0.4408	0.5765	0.7371	0.037*
C16	0.37797 (15)	0.5246 (2)	0.61590 (10)	0.0297 (4)
H16	0.3416	0.4224	0.6248	0.036*
C17	0.37411 (13)	0.58889 (18)	0.53437 (10)	0.0230 (3)
N1	0.41205 (12)	0.77182 (16)	0.43877 (8)	0.0270 (3)
N2	0.34983 (11)	0.64249 (15)	0.40576 (8)	0.0238 (3)
N3	0.32342 (11)	0.52833 (16)	0.45819 (8)	0.0268 (3)
O1	0.35353 (11)	0.22907 (16)	−0.20936 (7)	0.0390 (3)
O2	0.45409 (10)	0.27407 (13)	0.11862 (7)	0.0294 (3)
O3	0.36540 (10)	0.55293 (13)	0.15124 (6)	0.0276 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0309 (9)	0.0366 (10)	0.0234 (9)	−0.0077 (7)	0.0045 (7)	0.0009 (7)
C2	0.0253 (8)	0.0294 (9)	0.0211 (8)	−0.0072 (7)	0.0044 (6)	−0.0002 (7)
C3	0.0268 (8)	0.0220 (8)	0.0261 (9)	−0.0023 (6)	0.0065 (7)	−0.0018 (7)
C4	0.0248 (8)	0.0234 (8)	0.0216 (8)	−0.0019 (6)	0.0036 (6)	0.0017 (6)
C5	0.0251 (8)	0.0246 (8)	0.0197 (8)	−0.0027 (6)	0.0043 (6)	0.0001 (6)
C6	0.0308 (9)	0.0238 (8)	0.0252 (9)	0.0024 (7)	0.0048 (7)	0.0007 (7)
C7	0.0306 (9)	0.0300 (9)	0.0235 (9)	−0.0018 (7)	0.0022 (7)	0.0062 (7)
C8	0.0442 (10)	0.0256 (9)	0.0302 (9)	0.0090 (7)	0.0047 (8)	0.0024 (7)
C9	0.0361 (9)	0.0211 (8)	0.0235 (9)	0.0044 (7)	0.0053 (7)	−0.0003 (6)
C10	0.0326 (9)	0.0200 (8)	0.0248 (9)	0.0015 (6)	0.0035 (7)	−0.0016 (6)
C11	0.0282 (8)	0.0353 (9)	0.0204 (8)	−0.0035 (7)	0.0014 (6)	−0.0044 (7)
C12	0.0228 (8)	0.0257 (8)	0.0221 (8)	0.0018 (6)	0.0031 (6)	−0.0005 (6)
C13	0.0291 (9)	0.0275 (8)	0.0284 (9)	−0.0042 (7)	0.0014 (7)	−0.0023 (7)
C14	0.0283 (9)	0.0362 (10)	0.0226 (9)	0.0002 (7)	−0.0001 (7)	−0.0048 (7)
C15	0.0311 (9)	0.0368 (10)	0.0229 (9)	0.0029 (7)	0.0034 (7)	0.0043 (7)
C16	0.0332 (9)	0.0271 (9)	0.0294 (9)	−0.0010 (7)	0.0067 (7)	0.0038 (7)
C17	0.0216 (8)	0.0225 (8)	0.0244 (8)	0.0032 (6)	0.0026 (6)	−0.0021 (6)
N1	0.0311 (8)	0.0249 (7)	0.0238 (8)	−0.0048 (6)	0.0023 (6)	−0.0032 (6)
N2	0.0262 (7)	0.0238 (7)	0.0214 (7)	−0.0021 (5)	0.0041 (5)	−0.0019 (5)
N3	0.0293 (7)	0.0246 (7)	0.0265 (8)	−0.0008 (5)	0.0053 (6)	−0.0006 (6)
O1	0.0457 (8)	0.0429 (8)	0.0302 (7)	−0.0049 (6)	0.0113 (6)	−0.0098 (6)
O2	0.0402 (7)	0.0242 (6)	0.0225 (6)	0.0084 (5)	0.0022 (5)	0.0009 (5)
O3	0.0394 (7)	0.0226 (6)	0.0199 (6)	0.0061 (5)	0.0029 (5)	−0.0016 (4)

C1—O1	1.211 (2)	C9—H9B	0.9900
C1—C2	1.463 (2)	C10—C11	1.510 (2)
C1—H1	0.9500	C10—H10A	0.9900
C2—C7	1.381 (2)	C10—H10B	0.9900
C2—C3	1.400 (2)	C11—N2	1.459 (2)
C3—C4	1.373 (2)	C11—H11A	0.9900
C3—H3	0.9500	C11—H11B	0.9900
C4—O2	1.3723 (18)	C12—N1	1.352 (2)
C4—C5	1.413 (2)	C12—C17	1.403 (2)
C5—O3	1.3580 (18)	C12—C13	1.414 (2)
C5—C6	1.384 (2)	C13—C14	1.359 (2)
C6—C7	1.390 (2)	C13—H13	0.9500
C6—H6	0.9500	C14—C15	1.415 (2)
C7—H7	0.9500	C14—H14	0.9500
C8—O2	1.4220 (18)	C15—C16	1.363 (2)
C8—H8A	0.9800	C15—H15	0.9500
C8—H8B	0.9800	C16—C17	1.410 (2)
C8—H8C	0.9800	C16—H16	0.9500
C9—O3	1.4350 (18)	C17—N3	1.3543 (19)
C9—C10	1.509 (2)	N1—N2	1.3235 (17)
C9—H9A	0.9900	N2—N3	1.3261 (18)
O1—C1—C2	125.67 (16)	C11—C10—H10A	109.3
O1—C1—H1	117.2	C9—C10—H10B	109.3
C2—C1—H1	117.2	C11—C10—H10B	109.3
C7—C2—C3	119.71 (14)	H10A—C10—H10B	108.0
C7—C2—C1	119.55 (15)	N2—C11—C10	112.58 (13)
C3—C2—C1	120.74 (15)	N2—C11—H11A	109.1
C4—C3—C2	120.20 (15)	C10—C11—H11A	109.1
C4—C3—H3	119.9	N2—C11—H11B	109.1
C2—C3—H3	119.9	C10—C11—H11B	109.1
O2—C4—C3	125.16 (14)	H11A—C11—H11B	107.8
O2—C4—C5	114.95 (13)	N1—C12—C17	108.84 (13)
C3—C4—C5	119.89 (14)	N1—C12—C13	129.72 (15)
O3—C5—C6	124.97 (14)	C17—C12—C13	121.44 (15)
O3—C5—C4	115.28 (13)	C14—C13—C12	116.34 (15)
C6—C5—C4	119.76 (14)	C14—C13—H13	121.8
C5—C6—C7	119.77 (15)	C12—C13—H13	121.8
C5—C6—H6	120.1	C13—C14—C15	122.49 (15)
C7—C6—H6	120.1	C13—C14—H14	118.8
C2—C7—C6	120.67 (15)	C15—C14—H14	118.8
C2—C7—H7	119.7	C16—C15—C14	121.95 (15)
C6—C7—H7	119.7	C16—C15—H15	119.0
O2—C8—H8A	109.5	C14—C15—H15	119.0
O2—C8—H8B	109.5	C15—C16—C17	116.82 (15)
H8A—C8—H8B	109.5	C15—C16—H16	121.6
O2—C8—H8C	109.5	C17—C16—H16	121.6
H8A—C8—H8C	109.5	N3—C17—C12	108.39 (13)
H8B—C8—H8C	109.5	N3—C17—C16	130.65 (15)
O3—C9—C10	107.80 (12)	C12—C17—C16	120.96 (14)
O3—C9—H9A	110.1	N2—N1—C12	102.55 (12)
C10—C9—H9A	110.1	N1—N2—N3	117.59 (12)
O3—C9—H9B	110.1	N1—N2—C11	121.76 (12)
C10—C9—H9B	110.1	N3—N2—C11	120.63 (12)
H9A—C9—H9B	108.5	N2—N3—C17	102.64 (12)
C9—C10—C11	111.61 (13)	C4—O2—C8	116.40 (12)
C9—C10—H10A	109.3	C5—O3—C9	116.98 (11)
O1—C1—C2—C7	175.92 (16)	N1—C12—C17—N3	0.19 (17)
O1—C1—C2—C3	−4.6 (2)	C13—C12—C17—N3	179.28 (14)
C7—C2—C3—C4	0.0 (2)	N1—C12—C17—C16	179.98 (14)
C1—C2—C3—C4	−179.50 (14)	C13—C12—C17—C16	−0.9 (2)
C2—C3—C4—O2	179.09 (14)	C15—C16—C17—N3	−179.70 (15)
C2—C3—C4—C5	−1.0 (2)	C15—C16—C17—C12	0.5 (2)
O2—C4—C5—O3	1.43 (19)	C17—C12—N1—N2	−0.25 (16)
C3—C4—C5—O3	−178.48 (13)	C13—C12—N1—N2	−179.25 (16)
O2—C4—C5—C6	−178.82 (14)	C12—N1—N2—N3	0.26 (17)
C3—C4—C5—C6	1.3 (2)	C12—N1—N2—C11	178.47 (13)
O3—C5—C6—C7	179.23 (14)	C10—C11—N2—N1	17.3 (2)
C4—C5—C6—C7	−0.5 (2)	C10—C11—N2—N3	−164.51 (13)
C3—C2—C7—C6	0.8 (2)	N1—N2—N3—C17	−0.14 (17)
C1—C2—C7—C6	−179.71 (14)	C11—N2—N3—C17	−178.38 (13)
C5—C6—C7—C2	−0.5 (2)	C12—C17—N3—N2	−0.03 (16)
O3—C9—C10—C11	−63.91 (17)	C16—C17—N3—N2	−179.80 (15)
C9—C10—C11—N2	177.26 (13)	C3—C4—O2—C8	1.1 (2)
N1—C12—C13—C14	179.44 (15)	C5—C4—O2—C8	−178.83 (13)
C17—C12—C13—C14	0.6 (2)	C6—C5—O3—C9	−9.2 (2)
C12—C13—C14—C15	0.1 (2)	C4—C5—O3—C9	170.54 (13)
C13—C14—C15—C16	−0.5 (3)	C10—C9—O3—C5	−174.10 (12)
C14—C15—C16—C17	0.1 (2)