organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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4-Chloro-N-(3,4,5-tri­meth­oxy­benzyl­­idene)aniline

aDepartment of Science, Gorgan University of Agricultural Sciences and Natural Resources, Gorgan 49189-43464, Iran, and bInstitute of Physics of the ASCR, Na Slovance 2, 182 21 Prague 8, Czech Republic
*Correspondence e-mail: dusek@fzu.cz

(Received 22 December 2008; accepted 5 January 2009; online 8 January 2009)

The title compound, C16H16ClNO3, is a Schiff base displaying a trans configuration of the C=N double bond. In the crystal structure, inter­molecular C—H⋯N and bifurcated C—H⋯(O,O) hydrogen bonds are observed.

Related literature

For backgroud and related structures, see: Khalaji et al. (2008[Khalaji, A. D., Welter, R., Amirnasr, M. & Barry, A. H. (2008). Anal. Sci. 24, x139-x140.]); Khalaji & Harrison (2008[Khalaji, A. D. & Harrison, W. T. A. (2008). Anal. Sci. 24, x3-x4.]); Khalaji et al. (2007[Khalaji, A. D., Slawin, A. M. Z. & Woollins, J. D. (2007). Acta Cryst. E63, o4257.]); Zhang (2008[Zhang, H. (2008). Acta Cryst. E64, o1219.]); Akkurt et al. (2008[Akkurt, M., Jarrahpour, A. A., Aye, M., Gençaslan, M. & Büyükgüngör, O. (2008). Acta Cryst. E64, o2175-o2176.]); Kashmiri et al. (2008[Kashmiri, M. A., Tahir, M. N., Akhtar, M., Ahmed, M. & Hanif Ch, A. (2008). Acta Cryst. E64, o790.]); Ren & Jian (2008[Ren, X.-Y. & Jian, F.-F. (2008). Acta Cryst. E64, o2027.]). For the synthesis of the title compound, see: Khalaji & Ng (2008[Khalaji, A. D. & Ng, S. W. (2008). Acta Cryst. E64, o1771.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16ClNO3

  • Mr = 305.75

  • Monoclinic, P 21

  • a = 7.2012 (2) Å

  • b = 8.18700 (10) Å

  • c = 12.9734 (3) Å

  • β = 105.050 (2)°

  • V = 738.63 (3) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 2.37 mm−1

  • T = 120 K

  • 0.22 × 0.20 × 0.11 mm

Data collection
  • Oxford Diffraction Gemini diffractometer

  • Absorption correction: numerical [Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.]) in CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Oxford, England.])] Tmin = 0.680, Tmax = 0.809

  • 5670 measured reflections

  • 2225 independent reflections

  • 2039 reflections with I > 3σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.109

  • S = 1.93

  • 2225 reflections

  • 189 parameters

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.21 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 915 Friedel pairs

  • Flack parameter: 0.06 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C7—H7⋯O1i 0.96 2.59 3.177 (4) 119
C7—H7⋯O2i 0.96 2.51 3.471 (4) 178
C12—H12⋯N1ii 0.96 2.61 3.545 (5) 164
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+1]; (ii) [-x+1, y-{\script{1\over 2}}, -z].

Data collection: CrysAlis CCD (Oxford Diffraction, 2005[Oxford Diffraction (2005). CrysAlis CCD. Oxford Diffraction Ltd, Oxford, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Oxford, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); program(s) used to refine structure: JANA2006 (Petříček et al., 2007[Petříček, V., Dušek, M. & Palatinus, L. (2007). JANA2006. Institute of Physics, Praha, Czech Republic.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: JANA2006.

Supporting information


Comment top

Studies on the Schiff-base compounds, products of condensation between aldehydes (or ketones) and amines, have received a lot of attention in recent years, (Khalaji et al., 2008; Khalaji & Harrison, 2008; Khalaji et al.,2007; Zhang, 2008; Akkurt et al., 2008; Kashmiri et al., 2008; Ren & Jian, 2008). As a continuation of these studies we present the crystal structure of C16H16ClNO3.

The molecular structure of the title compound is shown in Fig. 1. Bond lengths and angles are comparable with those observed in similar compounds (Khalaji et al., 2008; Khalaji & Harrison, 2008; Khalaji et al.,2007; Zhang, 2008; Akkurt et al., 2008; Kashmiri et al., 2008; Ren & Jian, 2008). In the crystal structure, intermolecular C—H···N and C—H···O hydrogen bonds are observed.

Related literature top

For backgroud and related structures, see: Khalaji et al. (2008); Khalaji & Harrison (2008); Khalaji et al. (2007); Zhang (2008); Akkurt et al. (2008); Kashmiri et al. (2008); Ren & Jian (2008). For the synthesis of the title compound, see: Khalaji & Ng (2008).

Experimental top

The title compound was synthesized using a method analogous to the literature procedure of Khalaji and Ng (2008). Crystals appropriate for data collection were obtained by slow evaporation from methanol-chloroform (1:5 v/v) at a room temperature (yield 83%).

Refinement top

All the H atoms were found in difference Fourier maps, but they were constrained to ideal positions. The isotropic atomic displacement parameters of hydrogen atoms were set to 1.2Ueq of the parent atom.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2006 (Petříček et al., 2007); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006 (Petříček et al., 2007).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The packing of (I) viewed along a, with hydrogen bonds shown as dashed lines.
4-Chloro-N-(3,4,5-trimethoxybenzylidene)aniline top
Crystal data top
C16H16ClNO3F(000) = 320
Mr = 305.75Dx = 1.379 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ybCell parameters from 4239 reflections
a = 7.2012 (2) Åθ = 3.5–62.6°
b = 8.1870 (1) ŵ = 2.37 mm1
c = 12.9734 (3) ÅT = 120 K
β = 105.050 (2)°Prism, colorless
V = 738.63 (3) Å30.22 × 0.20 × 0.11 mm
Z = 2
Data collection top
Oxford Diffraction Gemini
diffractometer with Xcalibur goniometer, Atlas detector and Gemini ultra Cu source
2225 independent reflections
Radiation source: X-ray tube2039 reflections with I > 3σ(I)
Mirror monochromatorRint = 0.048
Detector resolution: 20.7567 pixels mm-1θmax = 62.7°, θmin = 3.5°
rotation method data acquisition using ω scansh = 87
Absorption correction: numerical
[based on the crystal shape, using the method implemented in CrysAlis RED (Oxford Diffraction, 2008) according to Clark & Reid (1995)]
k = 99
Tmin = 0.680, Tmax = 0.809l = 1414
5670 measured reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
wR(F2) = 0.109(Δ/σ)max = 0.013
S = 1.93Δρmax = 0.28 e Å3
2225 reflectionsΔρmin = 0.21 e Å3
189 parametersAbsolute structure: Flack (1983), 915 Friedel pairs
0 restraintsAbsolute structure parameter: 0.06 (2)
65 constraints
Crystal data top
C16H16ClNO3V = 738.63 (3) Å3
Mr = 305.75Z = 2
Monoclinic, P21Cu Kα radiation
a = 7.2012 (2) ŵ = 2.37 mm1
b = 8.1870 (1) ÅT = 120 K
c = 12.9734 (3) Å0.22 × 0.20 × 0.11 mm
β = 105.050 (2)°
Data collection top
Oxford Diffraction Gemini
diffractometer with Xcalibur goniometer, Atlas detector and Gemini ultra Cu source
2225 independent reflections
Absorption correction: numerical
[based on the crystal shape, using the method implemented in CrysAlis RED (Oxford Diffraction, 2008) according to Clark & Reid (1995)]
2039 reflections with I > 3σ(I)
Tmin = 0.680, Tmax = 0.809Rint = 0.048
5670 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.109Δρmax = 0.28 e Å3
S = 1.93Δρmin = 0.21 e Å3
2225 reflectionsAbsolute structure: Flack (1983), 915 Friedel pairs
189 parametersAbsolute structure parameter: 0.06 (2)
0 restraints
Special details top

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.

The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.00790 (13)0.16442 (1)0.00937 (6)0.0366 (3)
O11.2823 (3)0.6425 (3)0.64185 (15)0.0252 (7)
O21.4726 (3)0.8288 (3)0.53638 (16)0.0255 (7)
O31.3717 (3)0.8527 (3)0.32476 (16)0.0298 (8)
N10.7360 (4)0.5116 (4)0.2085 (2)0.0261 (10)
C11.2081 (4)0.6506 (4)0.5342 (2)0.0199 (9)
C21.3141 (5)0.7435 (4)0.4792 (2)0.0220 (10)
C31.2528 (5)0.7593 (4)0.3685 (3)0.0226 (11)
C41.0855 (4)0.6828 (4)0.3111 (2)0.0239 (10)
C50.9789 (5)0.5918 (4)0.3668 (2)0.0212 (10)
C61.0392 (5)0.5747 (4)0.4767 (2)0.0226 (11)
C70.7985 (5)0.5127 (4)0.3104 (2)0.0226 (10)
C80.5578 (5)0.4334 (4)0.1638 (2)0.0240 (10)
C90.4039 (4)0.4350 (4)0.2092 (2)0.0250 (11)
C100.2330 (5)0.3568 (4)0.1612 (2)0.0263 (11)
C110.2161 (5)0.2724 (4)0.0662 (2)0.0273 (11)
C120.3676 (5)0.2727 (4)0.0172 (3)0.0324 (12)
C130.5356 (5)0.3535 (5)0.0654 (2)0.0315 (12)
C141.1767 (5)0.5531 (5)0.7017 (3)0.0370 (13)
C151.6479 (5)0.7425 (5)0.5441 (3)0.0319 (12)
C161.3098 (5)0.8853 (5)0.2132 (3)0.0366 (14)
H41.0439680.6922860.2348450.0286*
H60.9647880.5105970.513410.0271*
H90.4159760.4914630.2754740.03*
H100.1269660.3608180.1932330.0316*
H120.3546530.2170790.0493980.0389*
H130.6389750.3552150.0312350.0378*
H14a1.2308130.5722640.7764970.0444*
H14b1.0449230.5881520.6820850.0444*
H14c1.1829750.438670.6869180.0444*
H15a1.7537390.8053080.5854710.0382*
H15b1.6432030.6389740.5780740.0382*
H15c1.6645540.7251270.4738440.0382*
H16a1.4016520.9548630.1929560.0439*
H16b1.2992410.7843870.1743830.0439*
H16c1.1868280.9384640.1971260.0439*
H70.7236790.4590980.3518030.0271*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0321 (4)0.0363 (4)0.0337 (4)0.0062 (4)0.0049 (3)0.0031 (4)
O10.0277 (12)0.0274 (12)0.0184 (10)0.0043 (10)0.0021 (8)0.0007 (9)
O20.0210 (12)0.0256 (12)0.0276 (11)0.0031 (9)0.0023 (9)0.0061 (9)
O30.0298 (13)0.0353 (12)0.0235 (11)0.0092 (11)0.0054 (10)0.0014 (10)
N10.0248 (16)0.0292 (15)0.0227 (15)0.0020 (12)0.0032 (12)0.0012 (11)
C10.0216 (16)0.0189 (14)0.0184 (14)0.0012 (14)0.0039 (11)0.0004 (13)
C20.0190 (16)0.0203 (15)0.0239 (17)0.0012 (13)0.0007 (13)0.0033 (12)
C30.0235 (18)0.0192 (17)0.0280 (17)0.0008 (13)0.0115 (14)0.0002 (12)
C40.0229 (17)0.0235 (17)0.0235 (15)0.0008 (14)0.0030 (12)0.0005 (13)
C50.0182 (18)0.0199 (15)0.0251 (17)0.0011 (12)0.0046 (14)0.0007 (12)
C60.0239 (19)0.0209 (17)0.0227 (17)0.0018 (13)0.0057 (13)0.0015 (12)
C70.0211 (17)0.0200 (16)0.0251 (17)0.0003 (13)0.0033 (13)0.0005 (13)
C80.0263 (17)0.0220 (16)0.0206 (16)0.0015 (15)0.0007 (13)0.0004 (13)
C90.0252 (18)0.0281 (18)0.0201 (16)0.0027 (15)0.0032 (13)0.0004 (13)
C100.0254 (19)0.0296 (18)0.0219 (17)0.0010 (14)0.0024 (13)0.0003 (14)
C110.034 (2)0.0230 (16)0.0191 (16)0.0008 (14)0.0037 (14)0.0007 (12)
C120.032 (2)0.0353 (19)0.0270 (18)0.0025 (16)0.0020 (15)0.0050 (14)
C130.032 (2)0.040 (2)0.0226 (17)0.0018 (16)0.0080 (14)0.0030 (15)
C140.035 (2)0.048 (2)0.0262 (19)0.0060 (18)0.0048 (15)0.0083 (16)
C150.0185 (18)0.0334 (18)0.040 (2)0.0021 (15)0.0018 (15)0.0018 (15)
C160.042 (2)0.043 (2)0.0260 (18)0.0086 (17)0.0097 (16)0.0074 (15)
Geometric parameters (Å, º) top
Cl1—C102.708 (3)C7—H70.96
Cl1—C111.732 (3)C8—C91.384 (5)
Cl1—C122.714 (4)C8—C131.406 (5)
O1—C11.362 (3)C9—C101.383 (4)
O1—C141.423 (5)C9—H90.96
O2—C21.379 (4)C10—C111.390 (5)
O2—C151.427 (4)C10—H100.96
O3—C31.375 (4)C11—C121.398 (6)
O3—C161.424 (4)C12—C131.378 (5)
N1—C71.282 (4)C12—H120.96
N1—C81.417 (4)C13—H130.96
C1—C21.397 (5)C14—H14a0.96
C1—C61.397 (4)C14—H14b0.96
C2—C31.395 (4)C14—H14c0.96
C3—C41.390 (4)C15—H15a0.96
C4—C51.398 (5)C15—H15b0.96
C4—H40.96C15—H15c0.96
C5—C61.385 (4)C16—H16a0.96
C5—C71.466 (4)C16—H16b0.96
C6—H60.96C16—H16c0.96
C10—Cl1—C1252.95 (11)C8—C9—H9119.2976
C1—O1—C14117.5 (2)C10—C9—H9119.2983
C2—O2—C15112.4 (3)C9—C10—C11119.5 (3)
C3—O3—C16117.3 (2)C9—C10—H10120.2657
C7—N1—C8117.6 (3)C11—C10—H10120.265
O1—C1—C2115.4 (3)C10—C11—C12120.2 (3)
O1—C1—C6125.5 (3)C11—C12—C13119.5 (3)
C2—C1—C6119.0 (3)C11—C12—H12120.2721
O2—C2—C1119.1 (3)C13—C12—H12120.2719
O2—C2—C3120.3 (3)C8—C13—C12120.9 (4)
C1—C2—C3120.5 (3)C8—C13—H13119.5347
O3—C3—C2114.3 (3)C12—C13—H13119.5353
O3—C3—C4125.1 (3)O1—C14—H14a109.4713
C2—C3—C4120.5 (3)O1—C14—H14b109.4711
C3—C4—C5118.6 (3)O1—C14—H14c109.4713
C3—C4—H4120.6757H14a—C14—H14b109.4712
C5—C4—H4120.6756H14a—C14—H14c109.4714
C4—C5—C6121.2 (3)H14b—C14—H14c109.471
C4—C5—C7120.8 (3)O2—C15—H15a109.4714
C6—C5—C7118.0 (3)O2—C15—H15b109.4711
C1—C6—C5120.1 (3)O2—C15—H15c109.4715
C1—C6—H6119.9695H15a—C15—H15b109.4705
C5—C6—H6119.9698H15a—C15—H15c109.4714
N1—C7—C5123.1 (3)H15b—C15—H15c109.4714
N1—C7—H7118.4336O3—C16—H16a109.4709
C5—C7—H7118.4335O3—C16—H16b109.4714
N1—C8—C9124.2 (3)O3—C16—H16c109.4711
N1—C8—C13117.3 (3)H16a—C16—H16b109.4712
C9—C8—C13118.4 (3)H16a—C16—H16c109.4712
C8—C9—C10121.4 (3)H16b—C16—H16c109.4715
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O1i0.962.593.177 (4)119
C7—H7···O2i0.962.513.471 (4)178
C12—H12···N1ii0.962.613.545 (5)164
Symmetry codes: (i) x+2, y1/2, z+1; (ii) x+1, y1/2, z.

Experimental details

Crystal data
Chemical formulaC16H16ClNO3
Mr305.75
Crystal system, space groupMonoclinic, P21
Temperature (K)120
a, b, c (Å)7.2012 (2), 8.1870 (1), 12.9734 (3)
β (°) 105.050 (2)
V3)738.63 (3)
Z2
Radiation typeCu Kα
µ (mm1)2.37
Crystal size (mm)0.22 × 0.20 × 0.11
Data collection
DiffractometerOxford Diffraction Gemini
diffractometer with Xcalibur goniometer, Atlas detector and Gemini ultra Cu source
Absorption correctionNumerical
[based on the crystal shape, using the method implemented in CrysAlis RED (Oxford Diffraction, 2008) according to Clark & Reid (1995)]
Tmin, Tmax0.680, 0.809
No. of measured, independent and
observed [I > 3σ(I)] reflections
5670, 2225, 2039
Rint0.048
(sin θ/λ)max1)0.576
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.109, 1.93
No. of reflections2225
No. of parameters189
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.21
Absolute structureFlack (1983), 915 Friedel pairs
Absolute structure parameter0.06 (2)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2008), SIR2002 (Burla et al., 2003), JANA2006 (Petříček et al., 2007), DIAMOND (Brandenburg & Putz, 2005).

Selected bond lengths (Å) top
Cl1—C102.708 (3)C1—C61.397 (4)
Cl1—C111.732 (3)C2—C31.395 (4)
Cl1—C122.714 (4)C3—C41.390 (4)
O1—C11.362 (3)C4—C51.398 (5)
O1—C141.423 (5)C5—C61.385 (4)
O2—C21.379 (4)C5—C71.466 (4)
O2—C151.427 (4)C8—C91.384 (5)
O3—C31.375 (4)C8—C131.406 (5)
O3—C161.424 (4)C9—C101.383 (4)
N1—C71.282 (4)C10—C111.390 (5)
N1—C81.417 (4)C11—C121.398 (6)
C1—C21.397 (5)C12—C131.378 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O1i0.962.593.177 (4)119
C7—H7···O2i0.962.513.471 (4)178
C12—H12···N1ii0.962.613.545 (5)164
Symmetry codes: (i) x+2, y1/2, z+1; (ii) x+1, y1/2, z.
 

Acknowledgements

We thank Gorgan University of Agricultural Sciences and Natural Resources (GUASNR) and the Institute of Physics of the ASCR (grant No 202/07/J007) for supporting this study. ADK thanks Dr Jan Fabry (Institute of Physics of ASCR) for his collaboration.

References

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