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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o1953.
Published online 2010 July 7. doi:  10.1107/S1600536810025894
PMCID: PMC3007282

2,3-Dimethyl-N-[(E)-2,4,5-trimeth­oxy­benzyl­idene]aniline

Abstract

In the title compound, C18H21NO3, the C=N bond has a trans conformation and the benzene rings are oriented at a dihedral angle of 61.32 (6)°. The C atoms of the three meth­oxy groups are all roughly coplanar with their attached ring [deviations = 0.219 (2), −0.097 (2) and −0.137 (2) Å]. In the crystal, a weak C—H(...)π inter­action may help to establish the packing.

Related literature

For background information on Schiff bases and related crystal structures, see: Tahir et al. (2010a [triangle],b [triangle]); Tariq et al. (2010 [triangle]).

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Object name is e-66-o1953-scheme1.jpg

Experimental

Crystal data

  • C18H21NO3
  • M r = 299.36
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1953-efi1.jpg
  • a = 7.0040 (2) Å
  • b = 11.0396 (4) Å
  • c = 11.1585 (4) Å
  • α = 73.941 (1)°
  • β = 76.022 (2)°
  • γ = 82.079 (1)°
  • V = 802.24 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 296 K
  • 0.32 × 0.14 × 0.12 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.980, T max = 0.985
  • 13855 measured reflections
  • 3957 independent reflections
  • 2935 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.139
  • S = 1.07
  • 3957 reflections
  • 204 parameters
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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: ORTEP-3 (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025894/hb5535sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025894/hb5535Isup2.hkl

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

Comment

We have reported crystal structures of Schiff bases synthesized from 2,3-dimethylaniline (Tahir et al., 2010a, 2010b), (Tariq et al., 2010) and in continuation of this work, we report herein the structure and synthesis of the title compound (I, Fig. 1).

In (I) the 2,3-dimethylaniline moiety A (C1–C8/N1) and the group B (C9—C15/O1/O2/O3) of 2,4,5-trimethoxybenzaldehyde are planar with r. m. s. deviations of 0.0184 and 0.0103 Å, respectively. The dihedral angle between A/B is 61.32 (6)°. The title molecule essentially consists of monomers. The packing may be stabilized through weak C—H···π (Table 1) interactions.

Experimental

Equimolar quantities of 2,3-dimethylaniline and 2,4,5-trimethoxybenzaldehyde were refluxed in methanol for 45 min resulting in violet solution. The solution was kept at room temperature which affoarded colorless prisms of (I) after 48 h.

Refinement

The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for all other H-atoms.

Figures

Fig. 1.
View of (I) with displacement ellipsoids drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii.

Crystal data

C18H21NO3Z = 2
Mr = 299.36F(000) = 320
Triclinic, P1Dx = 1.239 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.0040 (2) ÅCell parameters from 2938 reflections
b = 11.0396 (4) Åθ = 1.9–28.4°
c = 11.1585 (4) ŵ = 0.08 mm1
α = 73.941 (1)°T = 296 K
β = 76.022 (2)°Prism, colorless
γ = 82.079 (1)°0.32 × 0.14 × 0.12 mm
V = 802.24 (5) Å3

Data collection

Bruker Kappa APEXII CCD diffractometer3957 independent reflections
Radiation source: fine-focus sealed tube2935 reflections with I > 2σ(I)
graphiteRint = 0.024
Detector resolution: 7.5 pixels mm-1θmax = 28.4°, θmin = 1.9°
ω scansh = −7→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −14→14
Tmin = 0.980, Tmax = 0.985l = −14→14
13855 measured reflections

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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0685P)2 + 0.1056P] where P = (Fo2 + 2Fc2)/3
3957 reflections(Δ/σ)max < 0.001
204 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = −0.16 e Å3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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 > σ(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)

xyzUiso*/Ueq
O11.17927 (17)0.38228 (10)0.31146 (12)0.0704 (4)
O21.06960 (13)0.10870 (9)0.06502 (9)0.0499 (3)
O30.77474 (16)0.25536 (10)0.00283 (11)0.0649 (4)
N10.69274 (15)0.60252 (10)0.24254 (10)0.0448 (3)
C10.64619 (17)0.71547 (11)0.28410 (11)0.0393 (3)
C20.45691 (17)0.73509 (12)0.35802 (12)0.0408 (4)
C30.40689 (18)0.84878 (12)0.39403 (12)0.0447 (4)
C40.5412 (2)0.94029 (13)0.35392 (14)0.0528 (4)
C50.7257 (2)0.92062 (13)0.28035 (15)0.0567 (5)
C60.77862 (19)0.80817 (13)0.24555 (13)0.0491 (4)
C70.3148 (2)0.63405 (16)0.40020 (17)0.0641 (6)
C80.2084 (2)0.87330 (18)0.47689 (19)0.0722 (6)
C90.85705 (18)0.54088 (11)0.25246 (12)0.0410 (4)
C100.91943 (17)0.42826 (11)0.20390 (11)0.0390 (3)
C111.08153 (17)0.34815 (11)0.23517 (12)0.0417 (4)
C121.13627 (17)0.23966 (11)0.19044 (12)0.0414 (3)
C131.03063 (17)0.21157 (11)0.11341 (11)0.0387 (3)
C140.86709 (17)0.29209 (12)0.08024 (12)0.0425 (4)
C150.81463 (17)0.39796 (12)0.12541 (12)0.0423 (4)
C161.3221 (3)0.29635 (15)0.36533 (17)0.0657 (6)
C171.2405 (2)0.02807 (15)0.08431 (18)0.0666 (6)
C180.6215 (2)0.33758 (15)−0.04312 (16)0.0591 (5)
H40.506361.016410.377000.0633*
H50.814290.983090.254250.0681*
H60.903210.794540.196200.0589*
H7A0.305970.594260.489320.0961*
H7B0.360420.572090.351850.0961*
H7C0.187110.671050.386460.0961*
H8A0.200890.954880.493380.1082*
H8B0.191760.809430.556210.1082*
H8C0.106100.871190.433830.1082*
H90.940310.567960.291690.0492*
H121.244010.186240.212540.0496*
H160.706600.451110.103380.0507*
H16A1.264340.218580.412710.0986*
H16B1.369370.331440.421450.0986*
H16C1.430110.280350.298620.0986*
H17A1.354600.076000.051000.1000*
H17B1.25245−0.037520.041030.1000*
H17C1.23041−0.009080.174000.1000*
H18A0.517450.349260.027520.0886*
H18B0.571160.30185−0.097490.0886*
H18C0.671140.41771−0.090750.0886*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0813 (7)0.0513 (6)0.1068 (9)0.0226 (5)−0.0673 (7)−0.0385 (6)
O20.0521 (5)0.0475 (5)0.0571 (6)0.0132 (4)−0.0173 (4)−0.0280 (4)
O30.0709 (6)0.0633 (6)0.0850 (8)0.0239 (5)−0.0489 (6)−0.0447 (6)
N10.0471 (5)0.0455 (6)0.0486 (6)0.0100 (4)−0.0174 (5)−0.0234 (5)
C10.0439 (6)0.0405 (6)0.0376 (6)0.0082 (5)−0.0159 (5)−0.0157 (5)
C20.0414 (6)0.0433 (7)0.0412 (6)0.0045 (5)−0.0152 (5)−0.0145 (5)
C30.0444 (6)0.0457 (7)0.0455 (7)0.0107 (5)−0.0129 (5)−0.0179 (5)
C40.0636 (8)0.0377 (7)0.0588 (8)0.0078 (6)−0.0145 (7)−0.0195 (6)
C50.0616 (8)0.0425 (7)0.0634 (9)−0.0089 (6)−0.0045 (7)−0.0143 (6)
C60.0477 (7)0.0493 (8)0.0471 (7)0.0008 (6)−0.0032 (5)−0.0151 (6)
C70.0542 (8)0.0645 (10)0.0787 (11)−0.0084 (7)−0.0076 (7)−0.0305 (8)
C80.0537 (8)0.0756 (11)0.0892 (12)0.0108 (8)−0.0016 (8)−0.0435 (10)
C90.0447 (6)0.0393 (6)0.0437 (7)0.0041 (5)−0.0166 (5)−0.0157 (5)
C100.0398 (6)0.0378 (6)0.0417 (6)0.0044 (5)−0.0124 (5)−0.0141 (5)
C110.0427 (6)0.0398 (6)0.0483 (7)0.0020 (5)−0.0193 (5)−0.0145 (5)
C120.0366 (5)0.0388 (6)0.0498 (7)0.0066 (4)−0.0140 (5)−0.0133 (5)
C130.0387 (5)0.0383 (6)0.0392 (6)0.0039 (4)−0.0063 (5)−0.0150 (5)
C140.0420 (6)0.0463 (7)0.0449 (7)0.0059 (5)−0.0164 (5)−0.0192 (5)
C150.0388 (6)0.0444 (7)0.0477 (7)0.0100 (5)−0.0164 (5)−0.0185 (5)
C160.0718 (9)0.0584 (9)0.0833 (11)0.0144 (7)−0.0510 (9)−0.0240 (8)
C170.0627 (9)0.0577 (9)0.0902 (12)0.0253 (7)−0.0277 (8)−0.0407 (9)
C180.0555 (8)0.0674 (9)0.0649 (9)0.0080 (7)−0.0316 (7)−0.0240 (8)

Geometric parameters (Å, °)

O1—C111.3658 (18)C14—C151.3686 (19)
O1—C161.406 (2)C4—H40.9300
O2—C131.3559 (16)C5—H50.9300
O2—C171.4129 (19)C6—H60.9300
O3—C141.3656 (17)C7—H7A0.9600
O3—C181.407 (2)C7—H7B0.9600
N1—C11.4181 (17)C7—H7C0.9600
N1—C91.2664 (17)C8—H8A0.9600
C1—C21.4058 (17)C8—H8B0.9600
C1—C61.3849 (19)C8—H8C0.9600
C2—C31.3962 (19)C9—H90.9300
C2—C71.499 (2)C12—H120.9300
C3—C41.384 (2)C15—H160.9300
C3—C81.508 (2)C16—H16A0.9600
C4—C51.378 (2)C16—H16B0.9600
C5—C61.378 (2)C16—H16C0.9600
C9—C101.4625 (18)C17—H17A0.9600
C10—C111.3917 (18)C17—H17B0.9600
C10—C151.3993 (18)C17—H17C0.9600
C11—C121.3937 (18)C18—H18A0.9600
C12—C131.3785 (17)C18—H18B0.9600
C13—C141.4076 (18)C18—H18C0.9600
C11—O1—C16119.52 (12)C2—C7—H7A109.00
C13—O2—C17118.84 (11)C2—C7—H7B109.00
C14—O3—C18117.70 (12)C2—C7—H7C109.00
C1—N1—C9119.09 (11)H7A—C7—H7B109.00
N1—C1—C2118.33 (11)H7A—C7—H7C109.00
N1—C1—C6120.89 (11)H7B—C7—H7C109.00
C2—C1—C6120.63 (12)C3—C8—H8A109.00
C1—C2—C3118.61 (12)C3—C8—H8B109.00
C1—C2—C7120.36 (12)C3—C8—H8C109.00
C3—C2—C7121.00 (12)H8A—C8—H8B109.00
C2—C3—C4119.75 (12)H8A—C8—H8C109.00
C2—C3—C8120.94 (13)H8B—C8—H8C109.00
C4—C3—C8119.31 (13)N1—C9—H9119.00
C3—C4—C5121.16 (13)C10—C9—H9119.00
C4—C5—C6119.86 (14)C11—C12—H12120.00
C1—C6—C5119.98 (13)C13—C12—H12120.00
N1—C9—C10121.79 (12)C10—C15—H16119.00
C9—C10—C11121.37 (11)C14—C15—H16119.00
C9—C10—C15120.23 (11)O1—C16—H16A109.00
C11—C10—C15118.40 (11)O1—C16—H16B109.00
O1—C11—C10116.09 (11)O1—C16—H16C109.00
O1—C11—C12123.28 (12)H16A—C16—H16B109.00
C10—C11—C12120.63 (11)H16A—C16—H16C109.00
C11—C12—C13119.97 (12)H16B—C16—H16C109.00
O2—C13—C12125.10 (11)O2—C17—H17A109.00
O2—C13—C14114.82 (11)O2—C17—H17B109.00
C12—C13—C14120.08 (12)O2—C17—H17C109.00
O3—C14—C13114.95 (12)H17A—C17—H17B109.00
O3—C14—C15125.80 (12)H17A—C17—H17C110.00
C13—C14—C15119.25 (12)H17B—C17—H17C109.00
C10—C15—C14121.67 (12)O3—C18—H18A109.00
C3—C4—H4119.00O3—C18—H18B109.00
C5—C4—H4119.00O3—C18—H18C110.00
C4—C5—H5120.00H18A—C18—H18B109.00
C6—C5—H5120.00H18A—C18—H18C109.00
C1—C6—H6120.00H18B—C18—H18C109.00
C5—C6—H6120.00
C16—O1—C11—C10169.05 (13)C3—C4—C5—C60.1 (2)
C16—O1—C11—C12−10.5 (2)C4—C5—C6—C10.3 (2)
C17—O2—C13—C12−5.76 (19)N1—C9—C10—C11−168.10 (12)
C17—O2—C13—C14174.79 (12)N1—C9—C10—C1511.16 (19)
C18—O3—C14—C13−174.38 (12)C9—C10—C11—O1−1.04 (18)
C18—O3—C14—C155.2 (2)C9—C10—C11—C12178.53 (12)
C9—N1—C1—C2−134.93 (13)C15—C10—C11—O1179.69 (12)
C9—N1—C1—C649.51 (17)C15—C10—C11—C12−0.75 (18)
C1—N1—C9—C10−175.98 (11)C9—C10—C15—C14−178.84 (12)
N1—C1—C2—C3−176.94 (11)C11—C10—C15—C140.45 (19)
N1—C1—C2—C74.86 (18)O1—C11—C12—C13−179.82 (12)
C6—C1—C2—C3−1.38 (18)C10—C11—C12—C130.65 (19)
C6—C1—C2—C7−179.57 (13)C11—C12—C13—O2−179.65 (12)
N1—C1—C6—C5175.87 (12)C11—C12—C13—C14−0.23 (18)
C2—C1—C6—C50.4 (2)O2—C13—C14—O3−0.99 (16)
C1—C2—C3—C41.67 (19)O2—C13—C14—C15179.40 (11)
C1—C2—C3—C8−177.99 (13)C12—C13—C14—O3179.53 (11)
C7—C2—C3—C4179.86 (13)C12—C13—C14—C15−0.07 (19)
C7—C2—C3—C80.2 (2)O3—C14—C15—C10−179.60 (12)
C2—C3—C4—C5−1.0 (2)C13—C14—C15—C100.0 (2)
C8—C3—C4—C5178.63 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C16—H16B···Cg1i0.962.993.5694 (19)120

Symmetry codes: (i) −x+2, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5535).

References

  • Bruker (2005). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Tahir, M. N., Tariq, M. I., Ahmad, S., Sarfraz, M. & Ather, A. Q. (2010a). Acta Cryst. E66, o1562. [PMC free article] [PubMed]
  • Tahir, M. N., Tariq, M. I., Ahmad, S., Sarfraz, M. & Ather, A. Q. (2010b). Acta Cryst. E66, o1817. [PMC free article] [PubMed]
  • Tariq, M. I., Ahmad, S., Tahir, M. N., Sarfaraz, M. & Hussain, I. (2010). Acta Cryst. E66, o1561. [PMC free article] [PubMed]

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