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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1070.
Published online 2009 April 18. doi:  10.1107/S1600536809013348
PMCID: PMC2977750

4-Chloro-2-[(E)-2-(4-methoxy­phen­yl)ethyl­imino­meth­yl]phenol

Abstract

In the title Schiff base, C16H16ClNO2, the 2-(4-methoxy­phen­yl)ethyl (CH3OC6H4CH2CH2–; r.m.s. deviation = 0.10 Å) and 4-chloro-2-(imino­meth­yl)phenol (N=CHC6H3ClOH; r.m.s. deviation = 0.01 Å) portions are both essentially planar, the two parts being inclined at an angle of 61.8 (1)°. The hydroxy group forms a hydrogen bond to the imino N atom.

Related literature

The crystal structures of several Schiff bases derived by condensing aryl-2-ethyl­amines and substituted salicylaldehydes have been reported; see: Chatziefthimiou et al. (2006 [triangle]); Chohan et al. (2008 [triangle]); Coombs et al. (2005 [triangle]); Li et al. (2006 [triangle]); Räisänen et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1070-scheme1.jpg

Experimental

Crystal data

  • C16H16ClNO2
  • M r = 289.75
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1070-efi1.jpg
  • a = 5.7610 (2) Å
  • b = 7.7115 (3) Å
  • c = 15.7814 (5) Å
  • α = 82.420 (2)°
  • β = 89.320 (2)°
  • γ = 85.313 (2)°
  • V = 692.65 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 100 K
  • 0.25 × 0.25 × 0.03 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.934, T max = 0.992
  • 5284 measured reflections
  • 3036 independent reflections
  • 2235 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.099
  • S = 1.03
  • 3036 reflections
  • 186 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013348/sj2612sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013348/sj2612Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

2-(4-Methoxyphenyl)ethylamine (0.30 g, 2 mmol) and 5-chlorosalicylaldehyde (0.31 g, 2 mmol) were heated in ethanol (20 ml) for 1 h. The solution was set aside for the growth of crystals.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) fixed at 1.2–1.5U(C).

The hydroxy H-atom was located in a difference Fourier map, and was refined with a distance restraint of O–H 0.84±0.01 Å; its temperature factor was refined.

Figures

Fig. 1.
Thermal ellipsoid plot of C16H16ClNO2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C16H16ClNO2Z = 2
Mr = 289.75F(000) = 304
Triclinic, P1Dx = 1.389 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.7610 (2) ÅCell parameters from 1628 reflections
b = 7.7115 (3) Åθ = 2.7–28.2°
c = 15.7814 (5) ŵ = 0.28 mm1
α = 82.420 (2)°T = 100 K
β = 89.320 (2)°Plate, yellow
γ = 85.313 (2)°0.25 × 0.25 × 0.03 mm
V = 692.65 (4) Å3

Data collection

Bruker SMART APEX diffractometer3036 independent reflections
Radiation source: fine-focus sealed tube2235 reflections with I > 2σ(I)
graphiteRint = 0.025
ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→7
Tmin = 0.934, Tmax = 0.992k = −10→9
5284 measured reflectionsl = −20→20

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.033P)2 + 0.4582P] where P = (Fo2 + 2Fc2)/3
3036 reflections(Δ/σ)max = 0.001
186 parametersΔρmax = 0.28 e Å3
1 restraintΔρmin = −0.28 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl10.72711 (10)0.19401 (7)0.02737 (3)0.02303 (15)
O10.4122 (3)0.0304 (2)0.38188 (9)0.0209 (3)
H10.509 (4)0.068 (4)0.4137 (15)0.042 (8)*
O20.9991 (2)0.43513 (19)0.88357 (8)0.0184 (3)
N10.7683 (3)0.1729 (2)0.42911 (10)0.0157 (4)
C10.4895 (3)0.0673 (3)0.30093 (12)0.0147 (4)
C20.3616 (3)0.0202 (3)0.23431 (13)0.0168 (4)
H20.2243−0.03890.24650.020*
C30.4334 (4)0.0592 (3)0.15057 (13)0.0177 (4)
H30.34490.02820.10530.021*
C40.6357 (4)0.1440 (3)0.13294 (12)0.0161 (4)
C50.7667 (3)0.1895 (3)0.19782 (12)0.0150 (4)
H50.90560.24600.18470.018*
C60.6960 (3)0.1530 (2)0.28272 (12)0.0130 (4)
C70.8351 (3)0.2023 (3)0.35138 (12)0.0139 (4)
H70.97570.25640.33810.017*
C80.9076 (3)0.2214 (3)0.49754 (12)0.0157 (4)
H8A1.05240.26910.47370.019*
H8B0.95090.11650.53930.019*
C90.7660 (3)0.3591 (3)0.54177 (12)0.0159 (4)
H9A0.76980.47390.50560.019*
H9B0.60190.32930.54510.019*
C100.8459 (3)0.3790 (3)0.63111 (12)0.0142 (4)
C110.6936 (3)0.4703 (3)0.68291 (13)0.0158 (4)
H110.54820.52190.66030.019*
C120.7501 (4)0.4870 (3)0.76572 (13)0.0163 (4)
H120.64430.54980.79950.020*
C130.9625 (4)0.4120 (3)0.80025 (12)0.0159 (4)
C141.1189 (4)0.3236 (3)0.75010 (12)0.0152 (4)
H141.26520.27390.77260.018*
C151.0580 (3)0.3086 (3)0.66572 (13)0.0156 (4)
H151.16540.24860.63140.019*
C161.2113 (4)0.3563 (3)0.92316 (13)0.0212 (5)
H16A1.21470.38050.98250.032*
H16B1.34420.40540.89200.032*
H16C1.22020.22920.92200.032*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0271 (3)0.0286 (3)0.0145 (2)−0.0072 (2)0.0018 (2)−0.0036 (2)
O10.0214 (8)0.0262 (9)0.0161 (7)−0.0088 (7)0.0029 (6)−0.0026 (6)
O20.0195 (8)0.0215 (8)0.0141 (7)−0.0005 (6)−0.0014 (6)−0.0023 (6)
N10.0174 (9)0.0134 (9)0.0164 (8)−0.0008 (7)−0.0022 (7)−0.0024 (7)
C10.0144 (10)0.0119 (10)0.0172 (10)0.0019 (8)0.0020 (8)−0.0011 (8)
C20.0130 (10)0.0151 (10)0.0226 (11)−0.0015 (8)−0.0012 (8)−0.0033 (8)
C30.0171 (10)0.0153 (10)0.0211 (10)−0.0005 (8)−0.0045 (8)−0.0046 (8)
C40.0181 (11)0.0159 (10)0.0139 (9)0.0008 (8)0.0014 (8)−0.0016 (8)
C50.0144 (10)0.0118 (10)0.0185 (10)−0.0008 (8)−0.0001 (8)−0.0011 (8)
C60.0121 (10)0.0108 (10)0.0157 (9)0.0014 (8)−0.0030 (8)−0.0014 (8)
C70.0116 (10)0.0109 (10)0.0190 (10)−0.0001 (8)−0.0017 (8)−0.0011 (8)
C80.0167 (10)0.0141 (10)0.0162 (10)−0.0007 (8)−0.0019 (8)−0.0020 (8)
C90.0158 (10)0.0136 (10)0.0182 (10)−0.0010 (8)−0.0019 (8)−0.0022 (8)
C100.0149 (10)0.0112 (10)0.0167 (10)−0.0041 (8)0.0014 (8)−0.0010 (8)
C110.0119 (10)0.0133 (10)0.0217 (10)−0.0006 (8)−0.0001 (8)−0.0014 (8)
C120.0148 (10)0.0141 (10)0.0199 (10)0.0001 (8)0.0033 (8)−0.0030 (8)
C130.0203 (11)0.0137 (10)0.0138 (9)−0.0050 (8)0.0018 (8)−0.0008 (8)
C140.0128 (10)0.0147 (10)0.0179 (10)−0.0006 (8)−0.0005 (8)−0.0013 (8)
C150.0140 (10)0.0143 (10)0.0184 (10)−0.0003 (8)0.0023 (8)−0.0027 (8)
C160.0228 (11)0.0236 (12)0.0172 (10)−0.0034 (9)−0.0027 (9)−0.0022 (9)

Geometric parameters (Å, °)

Cl1—C41.745 (2)C8—H8A0.9900
O1—C11.350 (2)C8—H8B0.9900
O1—H10.849 (10)C9—C101.519 (3)
O2—C131.371 (2)C9—H9A0.9900
O2—C161.432 (3)C9—H9B0.9900
N1—C71.278 (2)C10—C151.384 (3)
N1—C81.458 (2)C10—C111.403 (3)
C1—C21.394 (3)C11—C121.375 (3)
C1—C61.415 (3)C11—H110.9500
C2—C31.382 (3)C12—C131.395 (3)
C2—H20.9500C12—H120.9500
C3—C41.390 (3)C13—C141.388 (3)
C3—H30.9500C14—C151.403 (3)
C4—C51.378 (3)C14—H140.9500
C5—C61.395 (3)C15—H150.9500
C5—H50.9500C16—H16A0.9800
C6—C71.463 (3)C16—H16B0.9800
C7—H70.9500C16—H16C0.9800
C8—C91.523 (3)
C1—O1—H1106.3 (19)C10—C9—C8115.68 (17)
C13—O2—C16117.54 (16)C10—C9—H9A108.4
C7—N1—C8120.28 (17)C8—C9—H9A108.4
O1—C1—C2118.87 (17)C10—C9—H9B108.4
O1—C1—C6121.37 (17)C8—C9—H9B108.4
C2—C1—C6119.77 (17)H9A—C9—H9B107.4
C3—C2—C1120.33 (18)C15—C10—C11117.62 (18)
C3—C2—H2119.8C15—C10—C9124.08 (18)
C1—C2—H2119.8C11—C10—C9118.28 (18)
C2—C3—C4119.71 (18)C12—C11—C10121.49 (19)
C2—C3—H3120.1C12—C11—H11119.3
C4—C3—H3120.1C10—C11—H11119.3
C5—C4—C3120.97 (18)C11—C12—C13120.15 (18)
C5—C4—Cl1119.05 (15)C11—C12—H12119.9
C3—C4—Cl1119.98 (15)C13—C12—H12119.9
C4—C5—C6120.20 (18)O2—C13—C14125.16 (19)
C4—C5—H5119.9O2—C13—C12115.10 (17)
C6—C5—H5119.9C14—C13—C12119.73 (18)
C5—C6—C1119.01 (17)C13—C14—C15119.15 (19)
C5—C6—C7120.01 (17)C13—C14—H14120.4
C1—C6—C7120.98 (17)C15—C14—H14120.4
N1—C7—C6120.31 (17)C10—C15—C14121.83 (18)
N1—C7—H7119.8C10—C15—H15119.1
C6—C7—H7119.8C14—C15—H15119.1
N1—C8—C9108.99 (16)O2—C16—H16A109.5
N1—C8—H8A109.9O2—C16—H16B109.5
C9—C8—H8A109.9H16A—C16—H16B109.5
N1—C8—H8B109.9O2—C16—H16C109.5
C9—C8—H8B109.9H16A—C16—H16C109.5
H8A—C8—H8B108.3H16B—C16—H16C109.5
O1—C1—C2—C3178.70 (19)C7—N1—C8—C9117.2 (2)
C6—C1—C2—C3−1.0 (3)N1—C8—C9—C10159.86 (16)
C1—C2—C3—C40.7 (3)C8—C9—C10—C1513.5 (3)
C2—C3—C4—C50.2 (3)C8—C9—C10—C11−164.78 (17)
C2—C3—C4—Cl1−179.87 (16)C15—C10—C11—C12−1.2 (3)
C3—C4—C5—C6−0.9 (3)C9—C10—C11—C12177.17 (18)
Cl1—C4—C5—C6179.22 (16)C10—C11—C12—C13−0.2 (3)
C4—C5—C6—C10.6 (3)C16—O2—C13—C14−2.5 (3)
C4—C5—C6—C7−179.72 (19)C16—O2—C13—C12178.17 (17)
O1—C1—C6—C5−179.34 (18)C11—C12—C13—O2−179.27 (18)
C2—C1—C6—C50.3 (3)C11—C12—C13—C141.4 (3)
O1—C1—C6—C71.0 (3)O2—C13—C14—C15179.56 (18)
C2—C1—C6—C7−179.37 (18)C12—C13—C14—C15−1.2 (3)
C8—N1—C7—C6179.71 (17)C11—C10—C15—C141.5 (3)
C5—C6—C7—N1178.33 (19)C9—C10—C15—C14−176.86 (18)
C1—C6—C7—N1−2.0 (3)C13—C14—C15—C10−0.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.85 (1)1.79 (2)2.567 (2)152 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2612).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chatziefthimiou, S. D., Lazarou, Y. G., Hadjoudis, E., Dziembowska, T. & Mavridis, I. M. (2006). J. Chem. Phys. B, 110, 23701–23709. [PubMed]
  • Chohan, Z. H., Shad, H. A., Tahir, M. N. & Khan, I. U. (2008). Acta Cryst. E64, o725. [PMC free article] [PubMed]
  • Coombs, R. R., Ringer, M. K., Blacquiere, J. M., Smith, J. S., Neilson, J. S., Uh, Y.-S., Gilbert, J. B., Leger, L. J., Zhang, H.-W., Irving, A. M., Wheaton, S. L., Wheaton, S. L., Vogels, C. M., Westcott, S. A., Decken, A. & Baerlocher, F. J. (2005). Transition Met. Chem.30, 411–418.
  • Li, Y.-G., Zhu, H.-L., Huang, W.-Q. & Ai, L. (2006). Acta Cryst. E62, o689–o690.
  • Räisänen, M. T., Leskelä, M. & Repo, T. (2007). Acta Cryst. E63, o1816–o1817.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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