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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046873/hb2193sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046873/hb2193Isup2.hkl
Contains datablock I

CCDC reference: 629839

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

No syntax errors found


No errors found in this datablock

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.

3-(4-Chlorobenzyloxy)-4-methoxybenzaldehyde top
Crystal data top
C15H13ClO3F(000) = 576
Mr = 276.70Dx = 1.372 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1316 reflections
a = 10.165 (11) Åθ = 2.4–23.2°
b = 16.752 (18) ŵ = 0.29 mm1
c = 7.874 (9) ÅT = 294 K
β = 92.54 (2)°Block, colorless
V = 1340 (3) Å30.26 × 0.24 × 0.16 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2343 independent reflections
Radiation source: fine-focus sealed tube1238 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 125
Tmin = 0.912, Tmax = 0.955k = 1918
5172 measured reflectionsl = 97
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.04P)2]
where P = (Fo2 + 2Fc2)/3
2343 reflections(Δ/σ)max = 0.003
173 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.24 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
Cl10.51582 (8)1.24700 (4)0.08417 (12)0.0814 (3)
O11.07261 (17)0.90988 (10)0.3623 (2)0.0667 (6)
O20.7451 (2)0.60856 (11)0.0954 (3)0.0847 (7)
O30.84836 (16)0.90972 (9)0.1986 (2)0.0577 (5)
C10.9017 (2)0.83641 (15)0.2305 (3)0.0478 (7)
C21.0252 (3)0.83652 (15)0.3188 (3)0.0503 (7)
C31.0889 (3)0.76608 (16)0.3588 (4)0.0560 (8)
H31.17030.76640.41740.067*
C41.0296 (3)0.69472 (16)0.3101 (4)0.0601 (8)
H41.07240.64700.33660.072*
C50.9094 (3)0.69271 (15)0.2239 (4)0.0522 (7)
C60.8458 (2)0.76459 (14)0.1838 (3)0.0511 (7)
H60.76450.76380.12470.061*
C71.1912 (3)0.91480 (16)0.4662 (4)0.0736 (9)
H7A1.18210.88350.56720.110*
H7B1.20780.96950.49690.110*
H7C1.26340.89470.40420.110*
C80.8511 (3)0.61712 (17)0.1698 (4)0.0689 (9)
H80.89950.57120.19450.083*
C90.7162 (2)0.91010 (14)0.1287 (4)0.0589 (8)
H9A0.66000.87890.19980.071*
H9B0.71310.88680.01580.071*
C100.6698 (2)0.99484 (15)0.1203 (4)0.0483 (7)
C110.5820 (3)1.02340 (16)0.2317 (4)0.0571 (8)
H110.55280.98960.31580.069*
C120.5350 (2)1.10078 (17)0.2239 (4)0.0586 (8)
H120.47591.11890.30200.070*
C130.5772 (3)1.15006 (15)0.0994 (4)0.0526 (8)
C140.6646 (3)1.12381 (16)0.0144 (4)0.0600 (8)
H140.69331.15770.09880.072*
C150.7101 (3)1.04639 (16)0.0027 (4)0.0587 (8)
H150.76981.02850.08030.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0915 (6)0.0474 (5)0.1035 (7)0.0151 (4)0.0168 (5)0.0069 (4)
O10.0663 (12)0.0473 (12)0.0836 (15)0.0030 (9)0.0292 (11)0.0039 (11)
O20.0684 (15)0.0558 (13)0.131 (2)0.0087 (11)0.0152 (14)0.0192 (13)
O30.0548 (11)0.0380 (11)0.0785 (14)0.0019 (8)0.0181 (10)0.0014 (10)
C10.0506 (16)0.0404 (16)0.0522 (18)0.0026 (13)0.0007 (13)0.0048 (14)
C20.0559 (17)0.0404 (16)0.0542 (19)0.0015 (14)0.0019 (14)0.0028 (15)
C30.0522 (16)0.0516 (18)0.064 (2)0.0076 (13)0.0045 (14)0.0056 (16)
C40.067 (2)0.0456 (18)0.069 (2)0.0130 (15)0.0112 (17)0.0082 (16)
C50.0606 (19)0.0362 (16)0.061 (2)0.0038 (13)0.0166 (15)0.0003 (15)
C60.0498 (15)0.0444 (18)0.059 (2)0.0027 (12)0.0019 (14)0.0003 (14)
C70.068 (2)0.068 (2)0.081 (2)0.0128 (15)0.0303 (17)0.0082 (18)
C80.068 (2)0.0450 (19)0.095 (3)0.0007 (16)0.0219 (19)0.0023 (18)
C90.0534 (17)0.0456 (17)0.076 (2)0.0009 (12)0.0156 (15)0.0039 (15)
C100.0450 (16)0.0403 (16)0.058 (2)0.0044 (12)0.0114 (14)0.0034 (16)
C110.0563 (18)0.0523 (19)0.062 (2)0.0094 (14)0.0078 (16)0.0052 (16)
C120.0526 (17)0.059 (2)0.063 (2)0.0023 (14)0.0018 (15)0.0090 (18)
C130.0520 (17)0.0423 (17)0.062 (2)0.0023 (13)0.0154 (15)0.0054 (16)
C140.078 (2)0.0421 (18)0.059 (2)0.0061 (15)0.0020 (17)0.0009 (15)
C150.0637 (18)0.0491 (18)0.063 (2)0.0018 (14)0.0036 (16)0.0104 (17)
Geometric parameters (Å, º) top
Cl1—C131.742 (3)C7—H7B0.9600
O1—C21.358 (3)C7—H7C0.9600
O1—C71.429 (3)C8—H80.9300
O2—C81.212 (3)C9—C101.497 (4)
O3—C11.361 (3)C9—H9A0.9700
O3—C91.429 (3)C9—H9B0.9700
C1—C61.374 (3)C10—C111.366 (4)
C1—C21.408 (4)C10—C151.373 (4)
C2—C31.376 (4)C11—C121.382 (4)
C3—C41.385 (4)C11—H110.9300
C3—H30.9300C12—C131.365 (4)
C4—C51.372 (4)C12—H120.9300
C4—H40.9300C13—C141.363 (4)
C5—C61.396 (3)C14—C151.379 (4)
C5—C81.454 (4)C14—H140.9300
C6—H60.9300C15—H150.9300
C7—H7A0.9600
C2—O1—C7118.5 (2)O2—C8—H8117.0
C1—O3—C9115.80 (18)C5—C8—H8117.0
O3—C1—C6125.7 (2)O3—C9—C10108.10 (19)
O3—C1—C2115.4 (2)O3—C9—H9A110.1
C6—C1—C2118.9 (2)C10—C9—H9A110.1
O1—C2—C3124.1 (3)O3—C9—H9B110.1
O1—C2—C1115.1 (2)C10—C9—H9B110.1
C3—C2—C1120.8 (2)H9A—C9—H9B108.4
C2—C3—C4118.9 (3)C11—C10—C15117.2 (3)
C2—C3—H3120.6C11—C10—C9121.2 (3)
C4—C3—H3120.6C15—C10—C9121.6 (3)
C5—C4—C3121.7 (2)C10—C11—C12122.3 (3)
C5—C4—H4119.2C10—C11—H11118.9
C3—C4—H4119.2C12—C11—H11118.9
C4—C5—C6119.0 (3)C13—C12—C11118.7 (3)
C4—C5—C8120.6 (3)C13—C12—H12120.6
C6—C5—C8120.4 (3)C11—C12—H12120.6
C1—C6—C5120.8 (3)C14—C13—C12120.8 (3)
C1—C6—H6119.6C14—C13—Cl1119.8 (2)
C5—C6—H6119.6C12—C13—Cl1119.4 (2)
O1—C7—H7A109.5C13—C14—C15119.1 (3)
O1—C7—H7B109.5C13—C14—H14120.5
H7A—C7—H7B109.5C15—C14—H14120.5
O1—C7—H7C109.5C10—C15—C14122.0 (3)
H7A—C7—H7C109.5C10—C15—H15119.0
H7B—C7—H7C109.5C14—C15—H15119.0
O2—C8—C5125.9 (3)
C9—O3—C1—C67.9 (4)C8—C5—C6—C1178.3 (3)
C9—O3—C1—C2172.3 (2)C4—C5—C8—O2178.9 (3)
C7—O1—C2—C34.7 (4)C6—C5—C8—O23.3 (5)
C7—O1—C2—C1174.1 (2)C1—O3—C9—C10173.9 (2)
O3—C1—C2—O11.1 (3)O3—C9—C10—C11105.9 (3)
C6—C1—C2—O1179.1 (2)O3—C9—C10—C1576.2 (3)
O3—C1—C2—C3179.9 (2)C15—C10—C11—C120.3 (4)
C6—C1—C2—C30.3 (4)C9—C10—C11—C12178.3 (2)
O1—C2—C3—C4178.9 (2)C10—C11—C12—C130.6 (4)
C1—C2—C3—C40.2 (4)C11—C12—C13—C140.5 (4)
C2—C3—C4—C50.2 (4)C11—C12—C13—Cl1178.3 (2)
C3—C4—C5—C60.3 (4)C12—C13—C14—C150.2 (4)
C3—C4—C5—C8178.1 (3)Cl1—C13—C14—C15178.6 (2)
O3—C1—C6—C5179.7 (2)C11—C10—C15—C140.0 (4)
C2—C1—C6—C50.4 (4)C9—C10—C15—C14178.0 (2)
C4—C5—C6—C10.4 (4)C13—C14—C15—C100.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O2i0.932.433.242 (5)146
C7—H7B···O2ii0.962.493.349 (5)148
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+2, y+1/2, z+1/2.
 

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