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In the title compound, C16H14Cl2O3, the ethylvanillin group makes a dihedral angle of 6.15 (3)° with the dichloro­benzene ring. Inter­molecular C—H...O inter­actions lead to trimeric associations of mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049671/hb2214sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049671/hb2214Isup2.hkl
Contains datablock I

CCDC reference: 629897

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.029
  • wR factor = 0.083
  • Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



Alert level B SYMMS02_ALERT_1_B The unit-cell lengths a and c should be equal for a rhombohedral cell Cell 19.8490 19.8490 10.3400 Angles 90.0000 90.0000 120.0000 SYMMS02_ALERT_1_B Cell angles alpha and gamma should be equal for a rhombohedral cell Cell 19.8490 19.8490 10.3400 Angles 90.0000 90.0000 120.0000 SYMMS02_ALERT_1_B All angles should not be 90 for a rhombohedral cell Cell 19.8490 19.8490 10.3400 Angles 90.0000 90.0000 120.0000
Alert level C PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O3 .. 3.23 Ang.
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 26.40 From the CIF: _reflns_number_total 1601 Count of symmetry unique reflns 1606 Completeness (_total/calc) 99.69% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 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.

4–4-(2,4-Dichlorobenzyloxy)-3-ethoxybenzaldehyde top
Crystal data top
C16H14Cl2O3F(000) = 1512
Mr = 325.17Dx = 1.378 Mg m3
Rhombohedral, R3Mo Kα radiation, λ = 0.71073 Å
Hall symbol: R 3Cell parameters from 2629 reflections
a = 19.849 (3) Åθ = 2.3–25.6°
c = 10.340 (2) ŵ = 0.42 mm1
α = 90°T = 294 K
γ = 120°Block, colorless
V = 3528.0 (10) Å30.26 × 0.24 × 0.20 mm
Z = 9
Data collection top
Bruker SMART APEX CCD
diffractometer
1601 independent reflections
Radiation source: fine-focus sealed tube1263 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ and ω scansθmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2424
Tmin = 0.878, Tmax = 0.919k = 1324
6567 measured reflectionsl = 1212
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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0472P)2 + 0.7953P]
where P = (Fo2 + 2Fc2)/3
1601 reflections(Δ/σ)max < 0.001
191 parametersΔρmax = 0.24 e Å3
1 restraintΔρmin = 0.18 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
Cl10.34754 (6)0.27838 (8)0.36798 (11)0.0759 (4)
Cl20.03498 (6)0.11165 (5)0.35177 (12)0.0645 (3)
O10.04996 (14)0.34052 (14)0.3773 (2)0.0490 (6)
O20.08296 (14)0.48186 (13)0.3796 (2)0.0494 (6)
O30.18716 (18)0.4669 (2)0.3739 (4)0.0851 (10)
C10.0130 (2)0.35061 (18)0.3790 (3)0.0399 (8)
C20.0054 (2)0.42927 (18)0.3809 (3)0.0395 (8)
C30.05343 (19)0.4456 (2)0.3825 (3)0.0436 (8)
H30.04170.49720.38540.052*
C40.1311 (2)0.3863 (2)0.3798 (4)0.0467 (8)
C50.1483 (2)0.3095 (2)0.3787 (4)0.0498 (8)
H50.20000.26980.37780.060*
C60.0890 (2)0.2909 (2)0.3787 (4)0.0464 (8)
H60.10070.23930.37860.056*
C70.1066 (2)0.56240 (19)0.3905 (4)0.0518 (9)
H7A0.08760.57190.47090.062*
H7B0.08560.57800.31930.062*
C80.1932 (2)0.6076 (3)0.3877 (4)0.0680 (12)
H8A0.21340.59250.45950.102*
H8B0.21060.66220.39360.102*
H8C0.21150.59730.30830.102*
C90.1945 (3)0.4037 (3)0.3779 (4)0.0617 (11)
H90.24500.36170.37990.074*
C100.0363 (2)0.26315 (17)0.3830 (4)0.0427 (8)
H10A0.00440.23300.31060.051*
H10B0.00950.23820.46250.051*
C110.11434 (19)0.26784 (18)0.3780 (3)0.0397 (7)
C120.1836 (2)0.3378 (2)0.3905 (4)0.0502 (8)
H120.18220.38370.40000.060*
C130.2549 (2)0.3407 (2)0.3891 (4)0.0536 (9)
H130.30080.38810.39800.064*
C140.2576 (2)0.2729 (2)0.3744 (3)0.0527 (9)
C150.1912 (2)0.2029 (2)0.3622 (4)0.0496 (8)
H150.19320.15730.35260.060*
C160.1198 (2)0.2014 (2)0.3646 (4)0.0467 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0493 (6)0.1038 (10)0.0871 (8)0.0477 (7)0.0021 (5)0.0068 (6)
Cl20.0511 (5)0.0338 (4)0.1065 (8)0.0196 (4)0.0117 (5)0.0054 (5)
O10.0402 (12)0.0350 (12)0.0758 (18)0.0219 (11)0.0015 (11)0.0022 (11)
O20.0390 (13)0.0362 (13)0.0725 (16)0.0184 (11)0.0033 (11)0.0023 (11)
O30.066 (2)0.076 (2)0.135 (3)0.0517 (19)0.0093 (18)0.0039 (19)
C10.0407 (18)0.0389 (18)0.0433 (19)0.0224 (15)0.0018 (14)0.0024 (14)
C20.0399 (17)0.0375 (16)0.0418 (19)0.0198 (15)0.0000 (13)0.0006 (13)
C30.0463 (19)0.0401 (18)0.053 (2)0.0280 (15)0.0007 (15)0.0011 (14)
C40.0417 (18)0.052 (2)0.0509 (19)0.0267 (17)0.0027 (15)0.0015 (16)
C50.0376 (18)0.048 (2)0.058 (2)0.0175 (16)0.0041 (15)0.0051 (17)
C60.0443 (18)0.0374 (18)0.054 (2)0.0177 (16)0.0013 (15)0.0012 (15)
C70.051 (2)0.0341 (18)0.067 (2)0.0187 (16)0.0009 (17)0.0056 (16)
C80.052 (2)0.050 (2)0.086 (3)0.0129 (19)0.003 (2)0.007 (2)
C90.045 (2)0.068 (3)0.078 (3)0.033 (2)0.0067 (18)0.005 (2)
C100.0412 (19)0.0344 (16)0.054 (2)0.0196 (15)0.0009 (15)0.0001 (14)
C110.0446 (18)0.0314 (17)0.0444 (19)0.0200 (15)0.0011 (14)0.0012 (12)
C120.049 (2)0.0348 (17)0.067 (2)0.0213 (16)0.0033 (17)0.0042 (16)
C130.0391 (18)0.0375 (19)0.073 (3)0.0106 (15)0.0024 (16)0.0033 (16)
C140.044 (2)0.067 (2)0.055 (2)0.034 (2)0.0024 (16)0.0079 (19)
C150.051 (2)0.048 (2)0.058 (2)0.0303 (17)0.0033 (16)0.0040 (17)
C160.0411 (18)0.0375 (17)0.059 (2)0.0180 (15)0.0064 (15)0.0045 (15)
Geometric parameters (Å, º) top
Cl1—C141.735 (4)C7—H7A0.9700
Cl2—C161.740 (4)C7—H7B0.9700
O1—C11.360 (4)C8—H8A0.9600
O1—C101.421 (4)C8—H8B0.9600
O2—C21.361 (4)C8—H8C0.9600
O2—C71.428 (4)C9—H90.9300
O3—C91.189 (5)C10—C111.505 (5)
C1—C61.376 (5)C10—H10A0.9700
C1—C21.415 (4)C10—H10B0.9700
C2—C31.359 (4)C11—C161.383 (5)
C3—C41.395 (5)C11—C121.388 (5)
C3—H30.9300C12—C131.389 (5)
C4—C51.386 (5)C12—H120.9300
C4—C91.463 (5)C13—C141.381 (5)
C5—C61.399 (5)C13—H130.9300
C5—H50.9300C14—C151.361 (5)
C6—H60.9300C15—C161.403 (5)
C7—C81.490 (5)C15—H150.9300
C1—O1—C10117.8 (3)H8A—C8—H8C109.5
C2—O2—C7118.1 (3)H8B—C8—H8C109.5
O1—C1—C6124.4 (3)O3—C9—C4125.7 (4)
O1—C1—C2114.5 (3)O3—C9—H9117.2
C6—C1—C2121.1 (3)C4—C9—H9117.2
C3—C2—O2126.5 (3)O1—C10—C11107.3 (3)
C3—C2—C1119.0 (3)O1—C10—H10A110.3
O2—C2—C1114.5 (3)C11—C10—H10A110.3
C2—C3—C4121.2 (3)O1—C10—H10B110.3
C2—C3—H3119.4C11—C10—H10B110.3
C4—C3—H3119.4H10A—C10—H10B108.5
C5—C4—C3119.2 (3)C16—C11—C12116.9 (3)
C5—C4—C9119.4 (3)C16—C11—C10120.9 (3)
C3—C4—C9121.3 (4)C12—C11—C10122.1 (3)
C4—C5—C6120.9 (3)C11—C12—C13121.3 (3)
C4—C5—H5119.6C11—C12—H12119.4
C6—C5—H5119.6C13—C12—H12119.4
C1—C6—C5118.5 (3)C14—C13—C12119.7 (3)
C1—C6—H6120.7C14—C13—H13120.1
C5—C6—H6120.7C12—C13—H13120.1
O2—C7—C8107.9 (3)C15—C14—C13121.1 (3)
O2—C7—H7A110.1C15—C14—Cl1120.0 (3)
C8—C7—H7A110.1C13—C14—Cl1118.9 (3)
O2—C7—H7B110.1C14—C15—C16118.1 (3)
C8—C7—H7B110.1C14—C15—H15120.9
H7A—C7—H7B108.4C16—C15—H15120.9
C7—C8—H8A109.5C11—C16—C15122.8 (3)
C7—C8—H8B109.5C11—C16—Cl2119.1 (3)
H8A—C8—H8B109.5C15—C16—Cl2118.1 (3)
C7—C8—H8C109.5
C10—O1—C1—C63.8 (5)C5—C4—C9—O3177.1 (4)
C10—O1—C1—C2176.4 (3)C3—C4—C9—O32.7 (7)
C7—O2—C2—C35.0 (5)C1—O1—C10—C11179.3 (3)
C7—O2—C2—C1175.7 (3)O1—C10—C11—C16171.3 (3)
O1—C1—C2—C3179.9 (3)O1—C10—C11—C1210.7 (5)
C6—C1—C2—C30.0 (5)C16—C11—C12—C130.2 (5)
O1—C1—C2—O20.5 (4)C10—C11—C12—C13178.2 (4)
C6—C1—C2—O2179.3 (3)C11—C12—C13—C140.3 (6)
O2—C2—C3—C4178.0 (3)C12—C13—C14—C150.5 (6)
C1—C2—C3—C41.2 (5)C12—C13—C14—Cl1178.0 (3)
C2—C3—C4—C51.6 (5)C13—C14—C15—C160.2 (6)
C2—C3—C4—C9178.3 (3)Cl1—C14—C15—C16178.3 (3)
C3—C4—C5—C60.7 (5)C12—C11—C16—C150.5 (6)
C9—C4—C5—C6179.1 (3)C10—C11—C16—C15178.6 (4)
O1—C1—C6—C5179.0 (3)C12—C11—C16—Cl2178.7 (3)
C2—C1—C6—C50.8 (5)C10—C11—C16—Cl20.7 (5)
C4—C5—C6—C10.5 (5)C14—C15—C16—C110.4 (6)
C2—O2—C7—C8179.5 (3)C14—C15—C16—Cl2178.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O3i0.932.523.429 (5)167
Symmetry code: (i) x+y1, x, z.
 

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