4-[3-(Bromo-meth-yl)benz-yloxy]-3-methoxy-benzaldehyde.

In the title compound, C(16)H(15)BrO(3), the dihedral angle between the mean planes of the two benzene rings is 76.64 (2)°. In the crystal structure, there are weak π-π stacking inter-actions, with a centroid-centroid distance of 3.724 (3) Å, as well as an inter-molecular C⋯Br distance [3.495 (2) Å] which is slightly less than the sum of the van der Waals radii for these atoms.

Related literature

For the applications of related compounds, see: Chen et al. (2001 ▶); Demestre et al. (2009 ▶); Liao et al. (2003 ▶); Xia & Hu (2004 ▶). For a related structure, see: Jin et al. (2009 ▶).

Experimental

Crystal data

C16H15BrO3

M = 335.19

Monoclinic,

a = 14.275 (3) Å

b = 11.791 (2) Å

c = 8.7315 (17) Å

β = 95.671 (3)°

V = 1462.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.82 mm−1

T = 298 K

0.08 × 0.08 × 0.06 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick,1996 ▶) T min = 0.798, T max = 0.845

7566 measured reflections

2777 independent reflections

2014 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.150

S = 1.07

2777 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −0.35 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011347/lh5019sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011347/lh5019Isup2.hkl

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

C16H15BrO3	F(000) = 680
Mr = 335.19	Dx = 1.522 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2434 reflections
a = 14.275 (3) Å	θ = 2.3–24.0°
b = 11.791 (2) Å	µ = 2.82 mm−1
c = 8.7315 (17) Å	T = 298 K
β = 95.671 (3)°	Block, colourless
V = 1462.5 (5) Å3	0.08 × 0.08 × 0.06 mm
Z = 4

Bruker SMART CCD diffractometer	2777 independent reflections
Radiation source: fine-focus sealed tube	2014 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 25.7°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick,1996)	h = −17→17
Tmin = 0.798, Tmax = 0.845	k = −14→14
7566 measured reflections	l = −10→5

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0765P)2 + 1.2302P] where P = (Fo2 + 2Fc2)/3
2777 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.85 e Å−3
0 restraints	Δρmin = −0.35 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
Br1	0.58913 (3)	0.68699 (4)	1.13810 (7)	0.0709 (3)
C1	−0.0081 (3)	1.0150 (5)	0.1918 (5)	0.0559 (11)
H1	−0.0372	0.9491	0.1526	0.067*
C2	0.0624 (3)	1.0028 (4)	0.3238 (5)	0.0450 (9)
C3	0.1048 (3)	1.0973 (3)	0.3971 (5)	0.0437 (9)
H3	0.0915	1.1693	0.3572	0.052*
C4	0.1657 (3)	1.0851 (3)	0.5270 (4)	0.0409 (9)
C5	0.1854 (3)	0.9748 (3)	0.5878 (5)	0.0411 (9)
C6	0.1453 (3)	0.8818 (4)	0.5123 (5)	0.0483 (10)
H6	0.1598	0.8093	0.5493	0.058*
C7	0.0832 (3)	0.8959 (4)	0.3805 (5)	0.0492 (10)
H7	0.0556	0.8328	0.3305	0.059*
C8	0.1941 (3)	1.2830 (4)	0.5499 (6)	0.0532 (11)
H8A	0.2168	1.2873	0.4502	0.080*
H8B	0.2278	1.3363	0.6180	0.080*
H8C	0.1282	1.3007	0.5412	0.080*
C9	0.2625 (3)	0.8629 (3)	0.7868 (5)	0.0561 (12)
H9A	0.2991	0.8176	0.7216	0.067*
H9B	0.2040	0.8234	0.7983	0.067*
C10	0.3167 (3)	0.8807 (3)	0.9420 (5)	0.0446 (10)
C11	0.4120 (3)	0.8598 (3)	0.9632 (5)	0.0482 (10)
H11	0.4430	0.8359	0.8802	0.058*
C12	0.4628 (3)	0.8737 (3)	1.1059 (5)	0.0486 (10)
C13	0.4153 (4)	0.9079 (3)	1.2281 (5)	0.0576 (12)
H13	0.4481	0.9167	1.3247	0.069*
C14	0.3197 (3)	0.9293 (4)	1.2093 (6)	0.0581 (12)
H14	0.2886	0.9527	1.2925	0.070*
C15	0.2709 (3)	0.9158 (3)	1.0667 (6)	0.0530 (11)
H15	0.2065	0.9303	1.0537	0.064*
C16	0.5658 (3)	0.8494 (4)	1.1234 (7)	0.0683 (14)
H16A	0.5948	0.8865	1.2153	0.082*
H16B	0.5942	0.8798	1.0356	0.082*
O1	−0.0319 (2)	1.1038 (3)	0.1288 (4)	0.0668 (9)
O2	0.2083 (2)	1.1717 (2)	0.6096 (3)	0.0501 (7)
O3	0.2435 (2)	0.9726 (2)	0.7192 (3)	0.0516 (7)

	U11	U22	U33	U12	U13	U23
Br1	0.0595 (3)	0.0524 (3)	0.0992 (5)	0.0119 (2)	0.0002 (3)	0.0131 (3)
C1	0.056 (3)	0.067 (3)	0.045 (3)	−0.005 (2)	0.003 (2)	−0.007 (2)
C2	0.040 (2)	0.056 (2)	0.040 (2)	−0.0003 (18)	0.0050 (18)	−0.003 (2)
C3	0.047 (2)	0.041 (2)	0.044 (2)	0.0044 (17)	0.0074 (19)	0.0016 (19)
C4	0.041 (2)	0.039 (2)	0.043 (2)	0.0013 (16)	0.0025 (18)	−0.0020 (18)
C5	0.041 (2)	0.040 (2)	0.042 (2)	0.0006 (16)	0.0021 (18)	−0.0009 (18)
C6	0.053 (2)	0.038 (2)	0.053 (3)	0.0029 (18)	0.004 (2)	0.0008 (19)
C7	0.049 (2)	0.048 (2)	0.050 (2)	−0.0055 (19)	0.002 (2)	−0.010 (2)
C8	0.063 (3)	0.039 (2)	0.055 (3)	0.0037 (19)	−0.007 (2)	0.000 (2)
C9	0.071 (3)	0.033 (2)	0.061 (3)	0.005 (2)	−0.011 (2)	0.007 (2)
C10	0.052 (2)	0.0263 (18)	0.054 (3)	0.0026 (16)	0.001 (2)	0.0082 (18)
C11	0.051 (2)	0.036 (2)	0.058 (3)	0.0052 (18)	0.008 (2)	0.006 (2)
C12	0.051 (2)	0.0295 (19)	0.064 (3)	0.0006 (17)	−0.002 (2)	0.009 (2)
C13	0.083 (3)	0.034 (2)	0.052 (3)	−0.001 (2)	−0.011 (2)	0.003 (2)
C14	0.072 (3)	0.039 (2)	0.064 (3)	0.001 (2)	0.016 (3)	−0.003 (2)
C15	0.050 (2)	0.033 (2)	0.075 (3)	0.0017 (18)	0.005 (2)	0.001 (2)
C16	0.058 (3)	0.046 (3)	0.098 (4)	−0.002 (2)	−0.009 (3)	0.013 (3)
O1	0.063 (2)	0.078 (2)	0.055 (2)	0.0041 (18)	−0.0122 (16)	0.0038 (19)
O2	0.0631 (18)	0.0365 (15)	0.0474 (17)	−0.0004 (13)	−0.0112 (14)	0.0001 (12)
O3	0.0621 (18)	0.0359 (14)	0.0536 (18)	0.0014 (13)	−0.0108 (15)	0.0060 (13)

Br1—C16	1.946 (5)	C8—H8C	0.9600
C1—O1	1.216 (6)	C9—O3	1.437 (5)
C1—C2	1.460 (6)	C9—C10	1.508 (6)
C1—H1	0.9300	C9—H9A	0.9700
C2—C7	1.376 (6)	C9—H9B	0.9700
C2—C3	1.393 (6)	C10—C11	1.376 (6)
C3—C4	1.367 (6)	C10—C15	1.388 (6)
C3—H3	0.9300	C11—C12	1.388 (6)
C4—O2	1.358 (5)	C11—H11	0.9300
C4—C5	1.422 (5)	C12—C13	1.380 (6)
C5—O3	1.348 (5)	C12—C16	1.492 (6)
C5—C6	1.375 (6)	C13—C14	1.381 (7)
C6—C7	1.392 (6)	C13—H13	0.9300
C6—H6	0.9300	C14—C15	1.375 (7)
C7—H7	0.9300	C14—H14	0.9300
C8—O2	1.420 (5)	C15—H15	0.9300
C8—H8A	0.9600	C16—H16A	0.9700
C8—H8B	0.9600	C16—H16B	0.9700
O1—C1—C2	125.6 (4)	O3—C9—H9B	110.2
O1—C1—H1	117.2	C10—C9—H9B	110.2
C2—C1—H1	117.2	H9A—C9—H9B	108.5
C7—C2—C3	120.0 (4)	C11—C10—C15	118.9 (4)
C7—C2—C1	118.7 (4)	C11—C10—C9	120.6 (4)
C3—C2—C1	121.2 (4)	C15—C10—C9	120.4 (4)
C4—C3—C2	120.6 (4)	C10—C11—C12	121.4 (4)
C4—C3—H3	119.7	C10—C11—H11	119.3
C2—C3—H3	119.7	C12—C11—H11	119.3
O2—C4—C3	125.2 (4)	C13—C12—C11	118.4 (4)
O2—C4—C5	115.3 (3)	C13—C12—C16	122.2 (5)
C3—C4—C5	119.5 (4)	C11—C12—C16	119.4 (4)
O3—C5—C6	125.8 (4)	C12—C13—C14	121.1 (4)
O3—C5—C4	114.7 (3)	C12—C13—H13	119.4
C6—C5—C4	119.5 (4)	C14—C13—H13	119.4
C5—C6—C7	120.1 (4)	C15—C14—C13	119.6 (4)
C5—C6—H6	119.9	C15—C14—H14	120.2
C7—C6—H6	119.9	C13—C14—H14	120.2
C2—C7—C6	120.3 (4)	C14—C15—C10	120.6 (4)
C2—C7—H7	119.9	C14—C15—H15	119.7
C6—C7—H7	119.9	C10—C15—H15	119.7
O2—C8—H8A	109.5	C12—C16—Br1	110.9 (3)
O2—C8—H8B	109.5	C12—C16—H16A	109.5
H8A—C8—H8B	109.5	Br1—C16—H16A	109.5
O2—C8—H8C	109.5	C12—C16—H16B	109.5
H8A—C8—H8C	109.5	Br1—C16—H16B	109.5
H8B—C8—H8C	109.5	H16A—C16—H16B	108.1
O3—C9—C10	107.6 (3)	C4—O2—C8	117.4 (3)
O3—C9—H9A	110.2	C5—O3—C9	116.2 (3)
C10—C9—H9A	110.2
O1—C1—C2—C7	−178.7 (4)	C15—C10—C11—C12	−0.4 (6)
O1—C1—C2—C3	4.6 (7)	C9—C10—C11—C12	−178.8 (4)
C7—C2—C3—C4	−1.3 (6)	C10—C11—C12—C13	0.8 (6)
C1—C2—C3—C4	175.4 (4)	C10—C11—C12—C16	179.7 (4)
C2—C3—C4—O2	−177.8 (4)	C11—C12—C13—C14	−0.8 (6)
C2—C3—C4—C5	−0.3 (6)	C16—C12—C13—C14	−179.7 (4)
O2—C4—C5—O3	0.2 (5)	C12—C13—C14—C15	0.3 (6)
C3—C4—C5—O3	−177.6 (3)	C13—C14—C15—C10	0.1 (6)
O2—C4—C5—C6	179.9 (4)	C11—C10—C15—C14	−0.1 (6)
C3—C4—C5—C6	2.1 (6)	C9—C10—C15—C14	178.3 (4)
O3—C5—C6—C7	177.3 (4)	C13—C12—C16—Br1	100.3 (5)
C4—C5—C6—C7	−2.5 (6)	C11—C12—C16—Br1	−78.6 (5)
C3—C2—C7—C6	1.0 (6)	C3—C4—O2—C8	−5.1 (6)
C1—C2—C7—C6	−175.8 (4)	C5—C4—O2—C8	177.3 (4)
C5—C6—C7—C2	0.9 (6)	C6—C5—O3—C9	−1.7 (6)
O3—C9—C10—C11	−104.6 (4)	C4—C5—O3—C9	178.0 (3)
O3—C9—C10—C15	77.0 (5)	C10—C9—O3—C5	−172.1 (3)