3-(2,4-Dichloro­benz­yloxy)-4-methoxy­benzaldehyde

In the title compound, C₁₅H₁₂Cl₂O₃, the isovanillin group makes a dihedral angle of 3.12 (12)° with the dichloro­benzene ring. Inter­molecular C—H...O hydrogen bonds help to consolidate the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.062
• wR factor = 0.132
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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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-(2,4-Dichlorobenzyloxy)-4-methoxybenzaldehyde

Crystal data

C15H12Cl2O3	F(000) = 640
Mr = 311.15	Dx = 1.466 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1769 reflections
a = 7.456 (3) Å	θ = 2.8–25.5°
b = 24.850 (9) Å	µ = 0.46 mm^−1
c = 8.370 (3) Å	T = 294 K
β = 114.616 (6)°	Block, colorless
V = 1409.9 (9) Å^3	0.24 × 0.20 × 0.16 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer	2436 independent reflections
Radiation source: fine-focus sealed tube	1493 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.878, Tmax = 0.929	k = −29→23
6657 measured reflections	l = −9→9

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0298P)^2 + 2.615P] where P = (Fo^2 + 2Fc^2)/3
2436 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.25 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	−0.12483 (18)	1.07054 (5)	−0.43832 (14)	0.0507 (4)
Cl2	0.1224 (2)	1.24919 (5)	−0.04717 (19)	0.0695 (4)
O1	0.2869 (4)	0.98630 (11)	0.0393 (3)	0.0392 (7)
O2	0.5345 (4)	0.94834 (11)	0.3315 (3)	0.0427 (8)
O3	−0.0167 (6)	0.81667 (13)	−0.3488 (4)	0.0669 (10)
C1	0.3049 (6)	0.93166 (16)	0.0448 (5)	0.0337 (10)
C2	0.2011 (6)	0.89705 (16)	−0.0913 (5)	0.0342 (10)
H2	0.1106	0.9106	−0.1980	0.041*
C3	0.2319 (6)	0.84147 (16)	−0.0689 (5)	0.0350 (10)
C4	0.3683 (6)	0.82153 (18)	0.0884 (6)	0.0450 (12)
H4	0.3905	0.7846	0.1022	0.054*
C5	0.4724 (6)	0.85582 (17)	0.2262 (5)	0.0385 (11)
H5	0.5629	0.8419	0.3324	0.046*
C6	0.4423 (6)	0.91050 (16)	0.2064 (5)	0.0328 (10)
C7	0.6489 (7)	0.9289 (2)	0.5065 (5)	0.0538 (13)
H7A	0.5699	0.9049	0.5403	0.081*
H7B	0.6904	0.9587	0.5866	0.081*
H7C	0.7626	0.9100	0.5094	0.081*
C8	0.1168 (7)	0.80416 (19)	−0.2109 (7)	0.0502 (12)
H8	0.1494	0.7678	−0.1932	0.060*
C9	0.1607 (6)	1.00970 (16)	−0.1258 (5)	0.0372 (10)
H9A	0.0282	0.9954	−0.1643	0.045*
H9B	0.2089	1.0010	−0.2139	0.045*
C10	0.1581 (5)	1.06911 (16)	−0.1042 (5)	0.0298 (9)
C11	0.0311 (6)	1.10111 (16)	−0.2409 (5)	0.0339 (10)
C12	0.0207 (6)	1.15587 (17)	−0.2283 (6)	0.0385 (11)
H12	−0.0638	1.1762	−0.3229	0.046*
C13	0.1389 (7)	1.17972 (16)	−0.0719 (6)	0.0408 (11)
C14	0.2699 (7)	1.15015 (17)	0.0674 (6)	0.0414 (11)
H14	0.3499	1.1670	0.1722	0.050*
C15	0.2804 (6)	1.09508 (17)	0.0486 (5)	0.0374 (10)
H15	0.3716	1.0751	0.1406	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0545 (7)	0.0533 (7)	0.0309 (6)	−0.0030 (6)	0.0045 (5)	−0.0004 (5)
Cl2	0.0852 (10)	0.0348 (6)	0.0807 (10)	−0.0030 (7)	0.0267 (8)	−0.0039 (7)
O1	0.0496 (18)	0.0294 (16)	0.0277 (15)	0.0015 (14)	0.0053 (14)	0.0030 (12)
O2	0.0470 (18)	0.0456 (18)	0.0248 (15)	−0.0048 (15)	0.0043 (13)	0.0033 (13)
O3	0.083 (3)	0.050 (2)	0.048 (2)	−0.005 (2)	0.007 (2)	−0.0052 (17)
C1	0.036 (2)	0.031 (2)	0.033 (2)	0.003 (2)	0.014 (2)	0.0015 (19)
C2	0.032 (2)	0.040 (3)	0.027 (2)	0.003 (2)	0.0091 (18)	0.0025 (19)
C3	0.039 (2)	0.034 (2)	0.039 (2)	−0.001 (2)	0.023 (2)	0.001 (2)
C4	0.049 (3)	0.034 (2)	0.053 (3)	0.006 (2)	0.022 (2)	0.008 (2)
C5	0.034 (2)	0.045 (3)	0.033 (2)	0.005 (2)	0.011 (2)	0.008 (2)
C6	0.030 (2)	0.035 (2)	0.031 (2)	0.0000 (19)	0.0096 (19)	0.0059 (19)
C7	0.050 (3)	0.061 (3)	0.034 (2)	−0.006 (3)	0.002 (2)	0.003 (2)
C8	0.062 (3)	0.034 (3)	0.058 (3)	−0.001 (2)	0.029 (3)	−0.002 (2)
C9	0.043 (3)	0.038 (3)	0.026 (2)	0.001 (2)	0.010 (2)	0.0036 (19)
C10	0.032 (2)	0.033 (2)	0.024 (2)	−0.0022 (19)	0.0115 (17)	0.0011 (18)
C11	0.036 (2)	0.035 (2)	0.029 (2)	0.000 (2)	0.0111 (19)	−0.0009 (18)
C12	0.038 (2)	0.039 (3)	0.037 (3)	0.006 (2)	0.015 (2)	0.009 (2)
C13	0.046 (3)	0.033 (2)	0.048 (3)	0.002 (2)	0.024 (2)	0.005 (2)
C14	0.046 (3)	0.044 (3)	0.034 (2)	−0.011 (2)	0.016 (2)	−0.011 (2)
C15	0.038 (2)	0.044 (3)	0.029 (2)	0.000 (2)	0.012 (2)	0.0035 (19)

Geometric parameters (Å, º)

Cl1—C11	1.749 (4)	C7—H7A	0.9600
Cl2—C13	1.749 (4)	C7—H7B	0.9600
O1—C1	1.363 (5)	C7—H7C	0.9600
O1—C9	1.432 (4)	C8—H8	0.9300
O2—C6	1.362 (5)	C9—C10	1.489 (5)
O2—C7	1.437 (5)	C9—H9A	0.9700
O3—C8	1.210 (5)	C9—H9B	0.9700
C1—C2	1.379 (5)	C10—C15	1.383 (5)
C1—C6	1.415 (5)	C10—C11	1.391 (5)
C2—C3	1.400 (5)	C11—C12	1.369 (5)
C2—H2	0.9300	C12—C13	1.371 (6)
C3—C4	1.378 (6)	C12—H12	0.9300
C3—C8	1.469 (6)	C13—C14	1.380 (6)
C4—C5	1.383 (6)	C14—C15	1.383 (6)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.376 (6)	C15—H15	0.9300
C5—H5	0.9300
C1—O1—C9	116.9 (3)	O3—C8—H8	117.2
C6—O2—C7	116.5 (3)	C3—C8—H8	117.2
O1—C1—C2	125.4 (3)	O1—C9—C10	108.8 (3)
O1—C1—C6	115.1 (3)	O1—C9—H9A	109.9
C2—C1—C6	119.5 (4)	C10—C9—H9A	109.9
C1—C2—C3	120.0 (4)	O1—C9—H9B	109.9
C1—C2—H2	120.0	C10—C9—H9B	109.9
C3—C2—H2	120.0	H9A—C9—H9B	108.3
C4—C3—C2	119.8 (4)	C15—C10—C11	117.0 (4)
C4—C3—C8	119.7 (4)	C15—C10—C9	122.6 (4)
C2—C3—C8	120.4 (4)	C11—C10—C9	120.4 (3)
C3—C4—C5	120.6 (4)	C12—C11—C10	123.0 (4)
C3—C4—H4	119.7	C12—C11—Cl1	117.9 (3)
C5—C4—H4	119.7	C10—C11—Cl1	119.1 (3)
C6—C5—C4	120.1 (4)	C11—C12—C13	117.9 (4)
C6—C5—H5	120.0	C11—C12—H12	121.0
C4—C5—H5	120.0	C13—C12—H12	121.0
O2—C6—C5	125.8 (4)	C12—C13—C14	121.6 (4)
O2—C6—C1	114.3 (3)	C12—C13—Cl2	119.4 (3)
C5—C6—C1	119.9 (4)	C14—C13—Cl2	119.0 (3)
O2—C7—H7A	109.5	C13—C14—C15	119.0 (4)
O2—C7—H7B	109.5	C13—C14—H14	120.5
H7A—C7—H7B	109.5	C15—C14—H14	120.5
O2—C7—H7C	109.5	C10—C15—C14	121.3 (4)
H7A—C7—H7C	109.5	C10—C15—H15	119.3
H7B—C7—H7C	109.5	C14—C15—H15	119.3
O3—C8—C3	125.5 (4)
C9—O1—C1—C2	−5.0 (6)	C2—C3—C8—O3	−4.7 (7)
C9—O1—C1—C6	175.4 (3)	C1—O1—C9—C10	179.1 (3)
O1—C1—C2—C3	−179.5 (4)	O1—C9—C10—C15	7.2 (6)
C6—C1—C2—C3	0.1 (6)	O1—C9—C10—C11	−173.6 (3)
C1—C2—C3—C4	−1.0 (6)	C15—C10—C11—C12	−1.4 (6)
C1—C2—C3—C8	177.7 (4)	C9—C10—C11—C12	179.4 (4)
C2—C3—C4—C5	1.4 (7)	C15—C10—C11—Cl1	179.2 (3)
C8—C3—C4—C5	−177.4 (4)	C9—C10—C11—Cl1	−0.1 (5)
C3—C4—C5—C6	−0.8 (7)	C10—C11—C12—C13	−1.3 (7)
C7—O2—C6—C5	−10.5 (6)	Cl1—C11—C12—C13	178.2 (3)
C7—O2—C6—C1	169.5 (4)	C11—C12—C13—C14	2.3 (7)
C4—C5—C6—O2	179.8 (4)	C11—C12—C13—Cl2	−177.2 (3)
C4—C5—C6—C1	−0.1 (6)	C12—C13—C14—C15	−0.6 (7)
O1—C1—C6—O2	0.2 (5)	Cl2—C13—C14—C15	178.9 (3)
C2—C1—C6—O2	−179.4 (4)	C11—C10—C15—C14	3.1 (6)
O1—C1—C6—C5	−179.8 (4)	C9—C10—C15—C14	−177.7 (4)
C2—C1—C6—C5	0.5 (6)	C13—C14—C15—C10	−2.2 (7)
C4—C3—C8—O3	174.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3^i	0.93	2.60	3.526 (5)	175

Symmetry code: (i) x+1/2, −y+3/2, z+1/2.