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In the title compound, C15H12Cl2O3, the vanillin group makes a dihedral angle of 4.47 (8)° with the dichloro­benzene ring. Inter­molecular C—H...O hydrogen bonds help to consolidate the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604863X/hb2206sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680604863X/hb2206Isup2.hkl
Contains datablock I

CCDC reference: 629891

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.104
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

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Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. O3 .. 2.62 Ang.
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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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.

4-(2,4-Dichlorobenzyloxy)-3-methoxybenzaldehyde top
Crystal data top
C15H12Cl2O3F(000) = 640
Mr = 311.15Dx = 1.429 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1761 reflections
a = 7.507 (4) Åθ = 2.7–23.4°
b = 24.436 (15) ŵ = 0.45 mm1
c = 8.386 (5) ÅT = 294 K
β = 109.945 (9)°Block, colorless
V = 1446.1 (15) Å30.20 × 0.16 × 0.10 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
2952 independent reflections
Radiation source: fine-focus sealed tube1663 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
φ and ω scansθmax = 26.5°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 69
Tmin = 0.903, Tmax = 0.956k = 3026
8038 measured reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0423P)2]
where P = (Fo2 + 2Fc2)/3
2952 reflections(Δ/σ)max = 0.003
182 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.21 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl10.40640 (9)0.43342 (3)0.06884 (8)0.0594 (2)
Cl20.60867 (11)0.24931 (3)0.44901 (10)0.0690 (3)
O10.7854 (2)0.51813 (6)0.53269 (18)0.0506 (5)
O21.0073 (2)0.55292 (6)0.82480 (19)0.0499 (5)
O30.8678 (3)0.78251 (8)0.5291 (3)0.0720 (6)
C10.8143 (3)0.57386 (9)0.5429 (3)0.0386 (6)
C20.9328 (3)0.59288 (9)0.7038 (3)0.0376 (6)
C30.9655 (3)0.64876 (10)0.7280 (3)0.0394 (6)
H31.04250.66160.83340.047*
C40.8840 (3)0.68624 (10)0.5954 (3)0.0410 (6)
C50.7693 (3)0.66679 (10)0.4373 (3)0.0457 (6)
H50.71600.69130.34900.055*
C60.7338 (3)0.61089 (10)0.4105 (3)0.0457 (6)
H60.65670.59830.30490.055*
C71.1066 (4)0.57153 (11)0.9956 (3)0.0591 (8)
H7A1.21790.59140.99820.089*
H7B1.14280.54061.07010.089*
H7C1.02520.59501.03190.089*
C80.9217 (4)0.74498 (11)0.6296 (4)0.0544 (7)
H80.99470.75440.74000.065*
C90.6702 (3)0.49546 (10)0.3730 (3)0.0450 (6)
H9A0.72680.50300.28720.054*
H9B0.54500.51180.33720.054*
C100.6556 (3)0.43428 (9)0.3942 (3)0.0374 (6)
C110.5384 (3)0.40173 (10)0.2623 (3)0.0389 (6)
C120.5208 (3)0.34542 (10)0.2762 (3)0.0416 (6)
H120.44120.32500.18660.050*
C130.6261 (3)0.32076 (10)0.4284 (3)0.0448 (6)
C140.7442 (3)0.35099 (10)0.5638 (3)0.0472 (6)
H140.81300.33380.66510.057*
C150.7579 (3)0.40749 (10)0.5453 (3)0.0445 (6)
H150.83700.42780.63560.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0642 (5)0.0624 (5)0.0392 (4)0.0021 (3)0.0016 (3)0.0018 (3)
Cl20.0751 (6)0.0401 (4)0.0807 (6)0.0040 (3)0.0121 (4)0.0013 (4)
O10.0664 (12)0.0390 (11)0.0368 (10)0.0046 (8)0.0053 (8)0.0051 (8)
O20.0678 (12)0.0396 (10)0.0340 (9)0.0039 (8)0.0066 (8)0.0016 (8)
O30.0885 (16)0.0462 (12)0.0777 (14)0.0026 (10)0.0236 (12)0.0172 (11)
C10.0442 (14)0.0339 (14)0.0371 (14)0.0014 (11)0.0129 (11)0.0046 (11)
C20.0417 (15)0.0384 (14)0.0337 (13)0.0031 (11)0.0141 (11)0.0004 (12)
C30.0402 (14)0.0412 (15)0.0340 (14)0.0036 (11)0.0091 (11)0.0037 (11)
C40.0401 (15)0.0389 (15)0.0445 (15)0.0010 (11)0.0153 (12)0.0021 (12)
C50.0475 (16)0.0419 (16)0.0441 (15)0.0016 (12)0.0108 (13)0.0093 (13)
C60.0470 (16)0.0483 (17)0.0355 (14)0.0002 (12)0.0061 (12)0.0001 (12)
C70.070 (2)0.0602 (18)0.0341 (14)0.0021 (14)0.0016 (13)0.0009 (13)
C80.0586 (19)0.0458 (18)0.0551 (17)0.0040 (13)0.0148 (14)0.0021 (15)
C90.0508 (16)0.0458 (16)0.0337 (13)0.0046 (12)0.0085 (12)0.0064 (12)
C100.0369 (14)0.0394 (14)0.0368 (13)0.0000 (11)0.0136 (11)0.0027 (11)
C110.0333 (13)0.0483 (16)0.0325 (13)0.0024 (11)0.0079 (11)0.0019 (11)
C120.0379 (14)0.0443 (15)0.0404 (15)0.0058 (11)0.0106 (12)0.0095 (12)
C130.0469 (16)0.0355 (14)0.0528 (16)0.0011 (11)0.0180 (13)0.0036 (13)
C140.0486 (16)0.0465 (16)0.0412 (15)0.0041 (12)0.0084 (12)0.0003 (13)
C150.0474 (16)0.0444 (16)0.0371 (14)0.0007 (12)0.0083 (12)0.0081 (12)
Geometric parameters (Å, º) top
Cl1—C111.765 (2)C7—H7A0.9600
Cl2—C131.764 (3)C7—H7B0.9600
O1—C11.377 (3)C7—H7C0.9600
O1—C91.434 (3)C8—H80.9300
O2—C21.381 (3)C9—C101.514 (3)
O2—C71.444 (3)C9—H9A0.9700
O3—C81.217 (3)C9—H9B0.9700
C1—C61.400 (3)C10—C151.400 (3)
C1—C21.417 (3)C10—C111.402 (3)
C2—C31.390 (3)C11—C121.391 (3)
C3—C41.409 (3)C12—C131.389 (3)
C3—H30.9300C12—H120.9300
C4—C51.395 (3)C13—C141.391 (3)
C4—C81.472 (3)C14—C151.397 (3)
C5—C61.395 (3)C14—H140.9300
C5—H50.9300C15—H150.9300
C6—H60.9300
C1—O1—C9118.18 (17)O3—C8—H8116.4
C2—O2—C7116.64 (18)C4—C8—H8116.4
O1—C1—C6125.0 (2)O1—C9—C10108.46 (18)
O1—C1—C2114.71 (19)O1—C9—H9A110.0
C6—C1—C2120.3 (2)C10—C9—H9A110.0
O2—C2—C3125.5 (2)O1—C9—H9B110.0
O2—C2—C1115.6 (2)C10—C9—H9B110.0
C3—C2—C1118.9 (2)H9A—C9—H9B108.4
C2—C3—C4121.0 (2)C15—C10—C11116.8 (2)
C2—C3—H3119.5C15—C10—C9121.9 (2)
C4—C3—H3119.5C11—C10—C9121.2 (2)
C5—C4—C3119.3 (2)C12—C11—C10123.2 (2)
C5—C4—C8122.2 (2)C12—C11—Cl1118.11 (17)
C3—C4—C8118.5 (2)C10—C11—Cl1118.73 (19)
C4—C5—C6120.6 (2)C13—C12—C11117.7 (2)
C4—C5—H5119.7C13—C12—H12121.1
C6—C5—H5119.7C11—C12—H12121.1
C5—C6—C1119.9 (2)C12—C13—C14121.6 (2)
C5—C6—H6120.1C12—C13—Cl2118.79 (18)
C1—C6—H6120.1C14—C13—Cl2119.57 (19)
O2—C7—H7A109.5C13—C14—C15119.0 (2)
O2—C7—H7B109.5C13—C14—H14120.5
H7A—C7—H7B109.5C15—C14—H14120.5
O2—C7—H7C109.5C14—C15—C10121.6 (2)
H7A—C7—H7C109.5C14—C15—H15119.2
H7B—C7—H7C109.5C10—C15—H15119.2
O3—C8—C4127.1 (3)
C9—O1—C1—C62.6 (3)C3—C4—C8—O3177.6 (2)
C9—O1—C1—C2178.75 (19)C1—O1—C9—C10178.71 (18)
C7—O2—C2—C38.5 (3)O1—C9—C10—C155.5 (3)
C7—O2—C2—C1171.7 (2)O1—C9—C10—C11174.7 (2)
O1—C1—C2—O22.2 (3)C15—C10—C11—C120.1 (3)
C6—C1—C2—O2179.1 (2)C9—C10—C11—C12179.9 (2)
O1—C1—C2—C3178.0 (2)C15—C10—C11—Cl1179.90 (17)
C6—C1—C2—C30.7 (3)C9—C10—C11—Cl10.0 (3)
O2—C2—C3—C4179.4 (2)C10—C11—C12—C130.4 (3)
C1—C2—C3—C40.4 (3)Cl1—C11—C12—C13179.55 (17)
C2—C3—C4—C50.3 (3)C11—C12—C13—C140.7 (3)
C2—C3—C4—C8179.1 (2)C11—C12—C13—Cl2179.34 (17)
C3—C4—C5—C60.6 (3)C12—C13—C14—C150.5 (4)
C8—C4—C5—C6178.8 (2)Cl2—C13—C14—C15179.48 (18)
C4—C5—C6—C10.3 (4)C13—C14—C15—C100.1 (4)
O1—C1—C6—C5178.2 (2)C11—C10—C15—C140.1 (3)
C2—C1—C6—C50.4 (4)C9—C10—C15—C14179.8 (2)
C5—C4—C8—O33.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O3i0.932.623.512 (3)161
Symmetry code: (i) x+1, y1/2, z+1/2.
 

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