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

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ISSN: 2056-9890

(E)-4-Chloro-N-(2,4,6-tri­methyl­benzyl­­idene)aniline

aCollege of Bioengineering, Zhejiang Chinese Medical University, Hangzhou 310053, People's Republic of China
*Correspondence e-mail: songzhongcheng@gmail.com

(Received 4 July 2011; accepted 6 July 2011; online 9 July 2011)

In the title compound, C16H16ClN, the dihedral angle between the benzene rings is 24.61 (13)°. In the crystal, only van der Waals inter­actions occur between neighbouring mol­ecules.

Related literature

For related structures, see: Nie (2008[Nie, Y. (2008). Acta Cryst. E64, o471.]); Cui et al. (2009[Cui, C., Meng, Q. & Wang, Y. (2009). Acta Cryst. E65, o2472.]); Sun et al. (2011a[Sun, L.-X., Yu, Y.-D. & Wei, G.-Y. (2011a). Acta Cryst. E67, o1564.],b[Sun, L.-X., Yu, Y.-D. & Wei, G.-Y. (2011b). Acta Cryst. E67, o1578.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16ClN

  • Mr = 257.75

  • Monoclinic, P 21 /c

  • a = 7.198 (2) Å

  • b = 12.398 (4) Å

  • c = 15.865 (5) Å

  • β = 102.296 (4)°

  • V = 1383.3 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.26 mm−1

  • T = 293 K

  • 0.31 × 0.30 × 0.29 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.924, Tmax = 0.929

  • 7071 measured reflections

  • 2553 independent reflections

  • 1593 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.136

  • S = 1.04

  • 2553 reflections

  • 167 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

We report here the crystal structure of the title new Schiff base compound, (I). In (I) (Fig. 1), the geometric parameters of the title compound agree well with reported similar structures (Nie, 2008; Cui et al., 2009; Sun et al., 2011a,b). The dihedral angle between the two aromatic rings in the Schiff base molecule is 24.61 (13)°,

Related literature top

For related structures, see: Nie (2008); Cui et al. (2009); Sun et al. (2011a,b).

Experimental top

A mixture of 2,4,6-trimethylbenzaldehyde (5 mmol), 4-chloroaniline (5 mmol) and methanol (40 ml) was refluxed for 2 h. It was then allowed to cool and filtered. Recrystallization of the crude product from methanol yielded colorless blocks of (I).

Refinement top

H atoms were positioned geometrically and refined using the riding-model approximation, with C—H = 0.93–0.96 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids for non-hydrogen atoms.
(E)-4-Chloro-N-(2,4,6-trimethylbenzylidene)aniline top
Crystal data top
C16H16ClNF(000) = 544
Mr = 257.75Dx = 1.238 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1950 reflections
a = 7.198 (2) Åθ = 2.6–24.8°
b = 12.398 (4) ŵ = 0.26 mm1
c = 15.865 (5) ÅT = 293 K
β = 102.296 (4)°Block, colorless
V = 1383.3 (7) Å30.31 × 0.30 × 0.29 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
2553 independent reflections
Radiation source: fine-focus sealed tube1593 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ϕ and ω scansθmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 88
Tmin = 0.924, Tmax = 0.929k = 1512
7071 measured reflectionsl = 1919
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.136 w = 1/[σ2(Fo2) + (0.0476P)2 + 0.5504P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2553 reflectionsΔρmax = 0.19 e Å3
167 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.024 (3)
Crystal data top
C16H16ClNV = 1383.3 (7) Å3
Mr = 257.75Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.198 (2) ŵ = 0.26 mm1
b = 12.398 (4) ÅT = 293 K
c = 15.865 (5) Å0.31 × 0.30 × 0.29 mm
β = 102.296 (4)°
Data collection top
Bruker APEXII CCD
diffractometer
2553 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
1593 reflections with I > 2σ(I)
Tmin = 0.924, Tmax = 0.929Rint = 0.042
7071 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.136H-atom parameters constrained
S = 1.04Δρmax = 0.19 e Å3
2553 reflectionsΔρmin = 0.16 e Å3
167 parameters
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 > 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) top
xyzUiso*/Ueq
C10.2061 (3)0.3177 (2)0.07427 (15)0.0528 (6)
C20.1376 (4)0.3161 (2)0.16278 (16)0.0607 (7)
H20.12040.24970.19060.073*
C30.0937 (4)0.4085 (2)0.21154 (16)0.0608 (7)
C40.1175 (3)0.5063 (2)0.16925 (16)0.0568 (7)
H40.08640.56920.20100.068*
C50.1867 (3)0.51398 (19)0.08065 (15)0.0489 (6)
C60.2323 (3)0.41907 (19)0.03188 (14)0.0451 (6)
C70.3158 (3)0.4292 (2)0.06073 (15)0.0504 (6)
H70.35520.49760.08110.061*
C80.2484 (5)0.2115 (2)0.02813 (18)0.0752 (8)
H8A0.22830.15380.06950.113*
H8B0.16550.20220.01140.113*
H8C0.37820.21070.00310.113*
C90.0207 (5)0.4020 (3)0.30862 (17)0.0902 (10)
H9A0.00000.47350.33190.135*
H9B0.09670.36260.32100.135*
H9C0.11290.36570.33420.135*
C100.2072 (4)0.6250 (2)0.04014 (17)0.0625 (7)
H10A0.15880.67810.08330.094*
H10B0.33900.63920.01630.094*
H10C0.13670.62810.00480.094*
C110.4309 (4)0.3741 (2)0.20165 (15)0.0544 (6)
C120.5466 (4)0.2942 (2)0.24460 (18)0.0742 (9)
H120.55840.22970.21620.089*
C130.6456 (4)0.3073 (2)0.32874 (18)0.0729 (8)
H130.72570.25320.35610.087*
C140.6243 (4)0.4007 (2)0.37115 (16)0.0589 (7)
C150.5060 (4)0.4801 (2)0.33155 (17)0.0704 (8)
H150.49030.54290.36130.085*
C160.4093 (4)0.4668 (2)0.24666 (17)0.0679 (8)
H160.32890.52110.21980.081*
Cl10.74755 (12)0.41813 (6)0.47717 (5)0.0868 (3)
N10.3387 (3)0.35391 (18)0.11479 (13)0.0642 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0509 (15)0.0545 (15)0.0543 (15)0.0032 (12)0.0145 (12)0.0052 (12)
C20.0647 (18)0.0620 (17)0.0567 (16)0.0099 (13)0.0161 (13)0.0195 (13)
C30.0560 (16)0.0773 (19)0.0477 (14)0.0106 (14)0.0076 (12)0.0068 (14)
C40.0553 (16)0.0606 (16)0.0514 (15)0.0046 (13)0.0042 (12)0.0065 (12)
C50.0395 (13)0.0540 (15)0.0532 (14)0.0032 (11)0.0097 (11)0.0038 (11)
C60.0386 (13)0.0526 (14)0.0451 (13)0.0037 (11)0.0113 (10)0.0036 (11)
C70.0478 (14)0.0525 (15)0.0507 (14)0.0031 (12)0.0097 (11)0.0070 (12)
C80.102 (2)0.0502 (16)0.0739 (19)0.0005 (15)0.0191 (17)0.0075 (13)
C90.098 (2)0.118 (3)0.0494 (16)0.013 (2)0.0029 (16)0.0095 (17)
C100.0644 (18)0.0555 (16)0.0653 (17)0.0012 (13)0.0087 (13)0.0035 (13)
C110.0577 (16)0.0568 (15)0.0468 (14)0.0031 (13)0.0067 (12)0.0032 (12)
C120.109 (2)0.0492 (15)0.0595 (17)0.0074 (16)0.0064 (16)0.0013 (13)
C130.091 (2)0.0588 (17)0.0618 (17)0.0151 (16)0.0005 (16)0.0133 (14)
C140.0611 (17)0.0606 (17)0.0495 (15)0.0013 (13)0.0004 (12)0.0066 (12)
C150.087 (2)0.0643 (18)0.0535 (16)0.0166 (16)0.0004 (15)0.0049 (13)
C160.075 (2)0.0669 (18)0.0560 (16)0.0206 (15)0.0018 (14)0.0017 (14)
Cl10.1009 (7)0.0845 (6)0.0590 (5)0.0013 (5)0.0189 (4)0.0027 (4)
N10.0795 (16)0.0600 (14)0.0491 (12)0.0032 (12)0.0049 (11)0.0004 (11)
Geometric parameters (Å, º) top
C1—C21.386 (3)C9—H9B0.9600
C1—C61.419 (3)C9—H9C0.9600
C1—C81.506 (3)C10—H10A0.9600
C2—C31.380 (4)C10—H10B0.9600
C2—H20.9300C10—H10C0.9600
C3—C41.379 (3)C11—C121.378 (4)
C3—C91.520 (3)C11—C161.379 (3)
C4—C51.391 (3)C11—N11.419 (3)
C4—H40.9300C12—C131.382 (4)
C5—C61.408 (3)C12—H120.9300
C5—C101.513 (3)C13—C141.364 (4)
C6—C71.469 (3)C13—H130.9300
C7—N11.254 (3)C14—C151.365 (4)
C7—H70.9300C14—Cl11.740 (3)
C8—H8A0.9600C15—C161.388 (4)
C8—H8B0.9600C15—H150.9300
C8—H8C0.9600C16—H160.9300
C9—H9A0.9600
C2—C1—C6118.4 (2)H9A—C9—H9B109.5
C2—C1—C8118.1 (2)C3—C9—H9C109.5
C6—C1—C8123.5 (2)H9A—C9—H9C109.5
C3—C2—C1123.1 (2)H9B—C9—H9C109.5
C3—C2—H2118.5C5—C10—H10A109.5
C1—C2—H2118.5C5—C10—H10B109.5
C4—C3—C2117.8 (2)H10A—C10—H10B109.5
C4—C3—C9121.3 (3)C5—C10—H10C109.5
C2—C3—C9120.8 (2)H10A—C10—H10C109.5
C3—C4—C5122.2 (2)H10B—C10—H10C109.5
C3—C4—H4118.9C12—C11—C16117.8 (2)
C5—C4—H4118.9C12—C11—N1117.5 (2)
C4—C5—C6119.3 (2)C16—C11—N1124.7 (2)
C4—C5—C10118.3 (2)C11—C12—C13121.7 (3)
C6—C5—C10122.4 (2)C11—C12—H12119.1
C5—C6—C1119.2 (2)C13—C12—H12119.1
C5—C6—C7118.4 (2)C14—C13—C12119.2 (2)
C1—C6—C7122.3 (2)C14—C13—H13120.4
N1—C7—C6125.9 (2)C12—C13—H13120.4
N1—C7—H7117.0C13—C14—C15120.7 (2)
C6—C7—H7117.0C13—C14—Cl1119.7 (2)
C1—C8—H8A109.5C15—C14—Cl1119.7 (2)
C1—C8—H8B109.5C14—C15—C16119.7 (3)
H8A—C8—H8B109.5C14—C15—H15120.1
C1—C8—H8C109.5C16—C15—H15120.1
H8A—C8—H8C109.5C11—C16—C15120.9 (3)
H8B—C8—H8C109.5C11—C16—H16119.6
C3—C9—H9A109.5C15—C16—H16119.6
C3—C9—H9B109.5C7—N1—C11119.9 (2)
C6—C1—C2—C30.0 (4)C5—C6—C7—N1169.1 (2)
C8—C1—C2—C3179.8 (2)C1—C6—C7—N114.4 (4)
C1—C2—C3—C40.8 (4)C16—C11—C12—C132.9 (4)
C1—C2—C3—C9179.4 (2)N1—C11—C12—C13178.6 (3)
C2—C3—C4—C51.2 (4)C11—C12—C13—C141.8 (5)
C9—C3—C4—C5179.0 (2)C12—C13—C14—C150.4 (4)
C3—C4—C5—C60.7 (4)C12—C13—C14—Cl1179.8 (2)
C3—C4—C5—C10179.8 (2)C13—C14—C15—C161.3 (4)
C4—C5—C6—C10.2 (3)Cl1—C14—C15—C16179.3 (2)
C10—C5—C6—C1178.9 (2)C12—C11—C16—C152.0 (4)
C4—C5—C6—C7176.4 (2)N1—C11—C16—C15179.6 (3)
C10—C5—C6—C74.5 (3)C14—C15—C16—C110.1 (5)
C2—C1—C6—C50.5 (3)C6—C7—N1—C11176.6 (2)
C8—C1—C6—C5179.3 (2)C12—C11—N1—C7143.8 (3)
C2—C1—C6—C7176.0 (2)C16—C11—N1—C737.8 (4)
C8—C1—C6—C74.2 (4)

Experimental details

Crystal data
Chemical formulaC16H16ClN
Mr257.75
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.198 (2), 12.398 (4), 15.865 (5)
β (°) 102.296 (4)
V3)1383.3 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.26
Crystal size (mm)0.31 × 0.30 × 0.29
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.924, 0.929
No. of measured, independent and
observed [I > 2σ(I)] reflections
7071, 2553, 1593
Rint0.042
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.136, 1.04
No. of reflections2553
No. of parameters167
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.16

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by Zhejiang Traditional Chinese Medicine University (project 2010ZZ07) and the Zhejiang Province Undergraduate Scientific and Technological Innovation Project (project 2010R410029). In addition, we also thank Zhejiang Province Administration of Traditional Chinese Medicine (project 2010ZQ002), the Education Department of Zhejiang Province (project Y201018556) and the Health Bureau of Zhejiang Province (project 2010KYB076).

References

First citationBruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCui, C., Meng, Q. & Wang, Y. (2009). Acta Cryst. E65, o2472.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationNie, Y. (2008). Acta Cryst. E64, o471.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSun, L.-X., Yu, Y.-D. & Wei, G.-Y. (2011a). Acta Cryst. E67, o1564.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSun, L.-X., Yu, Y.-D. & Wei, G.-Y. (2011b). Acta Cryst. E67, o1578.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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