3-(4-Chloro­benz­yloxy)-4-methoxy­benzaldehyde

In the title compound, C₁₅H₁₃ClO₃, the isovanillin group makes a dihedral angle of 81.31 (8)° with the chloro­benzene ring. The crystal structure is stabilized by inter­molecular C—H...O inter­actions, forming a two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.047
• wR factor = 0.111
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

3-(4-Chlorobenzyloxy)-4-methoxybenzaldehyde

Crystal data

C15H13ClO3	F(000) = 576
Mr = 276.70	Dx = 1.372 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1316 reflections
a = 10.165 (11) Å	θ = 2.4–23.2°
b = 16.752 (18) Å	µ = 0.29 mm^−1
c = 7.874 (9) Å	T = 294 K
β = 92.54 (2)°	Block, colorless
V = 1340 (3) Å^3	0.26 × 0.24 × 0.16 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2343 independent reflections
Radiation source: fine-focus sealed tube	1238 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→5
Tmin = 0.912, Tmax = 0.955	k = −19→18
5172 measured reflections	l = −9→7

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.04P)^2] where P = (Fo^2 + 2Fc^2)/3
2343 reflections	(Δ/σ)max = 0.003
173 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.51582 (8)	1.24700 (4)	0.08417 (12)	0.0814 (3)
O1	1.07261 (17)	0.90988 (10)	0.3623 (2)	0.0667 (6)
O2	0.7451 (2)	0.60856 (11)	0.0954 (3)	0.0847 (7)
O3	0.84836 (16)	0.90972 (9)	0.1986 (2)	0.0577 (5)
C1	0.9017 (2)	0.83641 (15)	0.2305 (3)	0.0478 (7)
C2	1.0252 (3)	0.83652 (15)	0.3188 (3)	0.0503 (7)
C3	1.0889 (3)	0.76608 (16)	0.3588 (4)	0.0560 (8)
H3	1.1703	0.7664	0.4174	0.067*
C4	1.0296 (3)	0.69472 (16)	0.3101 (4)	0.0601 (8)
H4	1.0724	0.6470	0.3366	0.072*
C5	0.9094 (3)	0.69271 (15)	0.2239 (4)	0.0522 (7)
C6	0.8458 (2)	0.76459 (14)	0.1838 (3)	0.0511 (7)
H6	0.7645	0.7638	0.1247	0.061*
C7	1.1912 (3)	0.91480 (16)	0.4662 (4)	0.0736 (9)
H7A	1.1821	0.8835	0.5672	0.110*
H7B	1.2078	0.9695	0.4969	0.110*
H7C	1.2634	0.8947	0.4042	0.110*
C8	0.8511 (3)	0.61712 (17)	0.1698 (4)	0.0689 (9)
H8	0.8995	0.5712	0.1945	0.083*
C9	0.7162 (2)	0.91010 (14)	0.1287 (4)	0.0589 (8)
H9A	0.6600	0.8789	0.1998	0.071*
H9B	0.7131	0.8868	0.0158	0.071*
C10	0.6698 (2)	0.99484 (15)	0.1203 (4)	0.0483 (7)
C11	0.5820 (3)	1.02340 (16)	0.2317 (4)	0.0571 (8)
H11	0.5528	0.9896	0.3158	0.069*
C12	0.5350 (2)	1.10078 (17)	0.2239 (4)	0.0586 (8)
H12	0.4759	1.1189	0.3020	0.070*
C13	0.5772 (3)	1.15006 (15)	0.0994 (4)	0.0526 (8)
C14	0.6646 (3)	1.12381 (16)	−0.0144 (4)	0.0600 (8)
H14	0.6933	1.1577	−0.0988	0.072*
C15	0.7101 (3)	1.04639 (16)	−0.0027 (4)	0.0587 (8)
H15	0.7698	1.0285	−0.0803	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0915 (6)	0.0474 (5)	0.1035 (7)	0.0151 (4)	−0.0168 (5)	−0.0069 (4)
O1	0.0663 (12)	0.0473 (12)	0.0836 (15)	−0.0030 (9)	−0.0292 (11)	0.0039 (11)
O2	0.0684 (15)	0.0558 (13)	0.131 (2)	−0.0087 (11)	0.0152 (14)	−0.0192 (13)
O3	0.0548 (11)	0.0380 (11)	0.0785 (14)	0.0019 (8)	−0.0181 (10)	0.0014 (10)
C1	0.0506 (16)	0.0404 (16)	0.0522 (18)	0.0026 (13)	0.0007 (13)	0.0048 (14)
C2	0.0559 (17)	0.0404 (16)	0.0542 (19)	−0.0015 (14)	−0.0019 (14)	0.0028 (15)
C3	0.0522 (16)	0.0516 (18)	0.064 (2)	0.0076 (13)	−0.0045 (14)	0.0056 (16)
C4	0.067 (2)	0.0456 (18)	0.069 (2)	0.0130 (15)	0.0112 (17)	0.0082 (16)
C5	0.0606 (19)	0.0362 (16)	0.061 (2)	0.0038 (13)	0.0166 (15)	0.0003 (15)
C6	0.0498 (15)	0.0444 (18)	0.059 (2)	−0.0027 (12)	0.0019 (14)	−0.0003 (14)
C7	0.068 (2)	0.068 (2)	0.081 (2)	−0.0128 (15)	−0.0303 (17)	0.0082 (18)
C8	0.068 (2)	0.0450 (19)	0.095 (3)	0.0007 (16)	0.0219 (19)	−0.0023 (18)
C9	0.0534 (17)	0.0456 (17)	0.076 (2)	−0.0009 (12)	−0.0156 (15)	−0.0039 (15)
C10	0.0450 (16)	0.0403 (16)	0.058 (2)	−0.0044 (12)	−0.0114 (14)	−0.0034 (16)
C11	0.0563 (18)	0.0523 (19)	0.062 (2)	−0.0094 (14)	−0.0078 (16)	0.0052 (16)
C12	0.0526 (17)	0.059 (2)	0.063 (2)	0.0023 (14)	−0.0018 (15)	−0.0090 (18)
C13	0.0520 (17)	0.0423 (17)	0.062 (2)	0.0023 (13)	−0.0154 (15)	−0.0054 (16)
C14	0.078 (2)	0.0421 (18)	0.059 (2)	−0.0061 (15)	−0.0020 (17)	0.0009 (15)
C15	0.0637 (18)	0.0491 (18)	0.063 (2)	0.0018 (14)	0.0036 (16)	−0.0104 (17)

Geometric parameters (Å, º)

Cl1—C13	1.742 (3)	C7—H7B	0.9600
O1—C2	1.358 (3)	C7—H7C	0.9600
O1—C7	1.429 (3)	C8—H8	0.9300
O2—C8	1.212 (3)	C9—C10	1.497 (4)
O3—C1	1.361 (3)	C9—H9A	0.9700
O3—C9	1.429 (3)	C9—H9B	0.9700
C1—C6	1.374 (3)	C10—C11	1.366 (4)
C1—C2	1.408 (4)	C10—C15	1.373 (4)
C2—C3	1.376 (4)	C11—C12	1.382 (4)
C3—C4	1.385 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.365 (4)
C4—C5	1.372 (4)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.363 (4)
C5—C6	1.396 (3)	C14—C15	1.379 (4)
C5—C8	1.454 (4)	C14—H14	0.9300
C6—H6	0.9300	C15—H15	0.9300
C7—H7A	0.9600
C2—O1—C7	118.5 (2)	O2—C8—H8	117.0
C1—O3—C9	115.80 (18)	C5—C8—H8	117.0
O3—C1—C6	125.7 (2)	O3—C9—C10	108.10 (19)
O3—C1—C2	115.4 (2)	O3—C9—H9A	110.1
C6—C1—C2	118.9 (2)	C10—C9—H9A	110.1
O1—C2—C3	124.1 (3)	O3—C9—H9B	110.1
O1—C2—C1	115.1 (2)	C10—C9—H9B	110.1
C3—C2—C1	120.8 (2)	H9A—C9—H9B	108.4
C2—C3—C4	118.9 (3)	C11—C10—C15	117.2 (3)
C2—C3—H3	120.6	C11—C10—C9	121.2 (3)
C4—C3—H3	120.6	C15—C10—C9	121.6 (3)
C5—C4—C3	121.7 (2)	C10—C11—C12	122.3 (3)
C5—C4—H4	119.2	C10—C11—H11	118.9
C3—C4—H4	119.2	C12—C11—H11	118.9
C4—C5—C6	119.0 (3)	C13—C12—C11	118.7 (3)
C4—C5—C8	120.6 (3)	C13—C12—H12	120.6
C6—C5—C8	120.4 (3)	C11—C12—H12	120.6
C1—C6—C5	120.8 (3)	C14—C13—C12	120.8 (3)
C1—C6—H6	119.6	C14—C13—Cl1	119.8 (2)
C5—C6—H6	119.6	C12—C13—Cl1	119.4 (2)
O1—C7—H7A	109.5	C13—C14—C15	119.1 (3)
O1—C7—H7B	109.5	C13—C14—H14	120.5
H7A—C7—H7B	109.5	C15—C14—H14	120.5
O1—C7—H7C	109.5	C10—C15—C14	122.0 (3)
H7A—C7—H7C	109.5	C10—C15—H15	119.0
H7B—C7—H7C	109.5	C14—C15—H15	119.0
O2—C8—C5	125.9 (3)
C9—O3—C1—C6	7.9 (4)	C8—C5—C6—C1	−178.3 (3)
C9—O3—C1—C2	−172.3 (2)	C4—C5—C8—O2	178.9 (3)
C7—O1—C2—C3	−4.7 (4)	C6—C5—C8—O2	−3.3 (5)
C7—O1—C2—C1	174.1 (2)	C1—O3—C9—C10	173.9 (2)
O3—C1—C2—O1	1.1 (3)	O3—C9—C10—C11	−105.9 (3)
C6—C1—C2—O1	−179.1 (2)	O3—C9—C10—C15	76.2 (3)
O3—C1—C2—C3	179.9 (2)	C15—C10—C11—C12	−0.3 (4)
C6—C1—C2—C3	−0.3 (4)	C9—C10—C11—C12	−178.3 (2)
O1—C2—C3—C4	178.9 (2)	C10—C11—C12—C13	0.6 (4)
C1—C2—C3—C4	0.2 (4)	C11—C12—C13—C14	−0.5 (4)
C2—C3—C4—C5	−0.2 (4)	C11—C12—C13—Cl1	178.3 (2)
C3—C4—C5—C6	0.3 (4)	C12—C13—C14—C15	0.2 (4)
C3—C4—C5—C8	178.1 (3)	Cl1—C13—C14—C15	−178.6 (2)
O3—C1—C6—C5	−179.7 (2)	C11—C10—C15—C14	0.0 (4)
C2—C1—C6—C5	0.4 (4)	C9—C10—C15—C14	178.0 (2)
C4—C5—C6—C1	−0.4 (4)	C13—C14—C15—C10	0.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2^i	0.93	2.43	3.242 (5)	146
C7—H7B···O2^ii	0.96	2.49	3.349 (5)	148

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+2, y+1/2, −z+1/2.