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

Guo, Y.; Pan, M.-X.; Xiang, H.; Liu, W.-H.; Song, Z.-C.

doi:10.1107/S1600536811027024

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1999

doi:10.1107/S1600536811027024

Open

access

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

Ying Guo,^a Meng-Xin Pan,^a Hai Xiang,^a Wen-Hong Liu ^a and Zhong-Cheng Song ^a ^*

^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 ); Cui et al. (2009 ); Sun et al. (2011a ,b ).

Experimental

Crystal data

C₁₆H₁₆ClN
M_r = 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 ) T_min = 0.924, T_max = 0.929
7071 measured reflections
2553 independent reflections
1593 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.136
S = 1.04
2553 reflections
167 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811027024/hb5944sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027024/hb5944Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811027024/hb5944Isup3.cml

checkCIF report

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).

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

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

C₁₆H₁₆ClN	F(000) = 544
M_r = 257.75	D_x = 1.238 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1950 reflections
a = 7.198 (2) Å	θ = 2.6–24.8°
b = 12.398 (4) Å	µ = 0.26 mm⁻¹
c = 15.865 (5) Å	T = 293 K
β = 102.296 (4)°	Block, colorless
V = 1383.3 (7) Å³	0.31 × 0.30 × 0.29 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2553 independent reflections
Radiation source: fine-focus sealed tube	1593 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→8
T_min = 0.924, T_max = 0.929	k = −15→12
7071 measured reflections	l = −19→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.136	w = 1/[σ²(F_o²) + (0.0476P)² + 0.5504P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2553 reflections	Δρ_max = 0.19 e Å⁻³
167 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (3)

Crystal data top

C₁₆H₁₆ClN	V = 1383.3 (7) Å³
M_r = 257.75	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.198 (2) Å	µ = 0.26 mm⁻¹
b = 12.398 (4) Å	T = 293 K
c = 15.865 (5) Å	0.31 × 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)
T_min = 0.924, T_max = 0.929	R_int = 0.042
7071 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.04	Δρ_max = 0.19 e Å⁻³
2553 reflections	Δρ_min = −0.16 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C1	0.2061 (3)	0.3177 (2)	−0.07427 (15)	0.0528 (6)
C2	0.1376 (4)	0.3161 (2)	−0.16278 (16)	0.0607 (7)
H2	0.1204	0.2497	−0.1906	0.073*
C3	0.0937 (4)	0.4085 (2)	−0.21154 (16)	0.0608 (7)
C4	0.1175 (3)	0.5063 (2)	−0.16925 (16)	0.0568 (7)
H4	0.0864	0.5692	−0.2010	0.068*
C5	0.1867 (3)	0.51398 (19)	−0.08065 (15)	0.0489 (6)
C6	0.2323 (3)	0.41907 (19)	−0.03188 (14)	0.0451 (6)
C7	0.3158 (3)	0.4292 (2)	0.06073 (15)	0.0504 (6)
H7	0.3552	0.4976	0.0811	0.061*
C8	0.2484 (5)	0.2115 (2)	−0.02813 (18)	0.0752 (8)
H8A	0.2283	0.1538	−0.0695	0.113*
H8B	0.1655	0.2022	0.0114	0.113*
H8C	0.3782	0.2107	0.0031	0.113*
C9	0.0207 (5)	0.4020 (3)	−0.30862 (17)	0.0902 (10)
H9A	0.0000	0.4735	−0.3319	0.135*
H9B	−0.0967	0.3626	−0.3210	0.135*
H9C	0.1129	0.3657	−0.3342	0.135*
C10	0.2072 (4)	0.6250 (2)	−0.04014 (17)	0.0625 (7)
H10A	0.1588	0.6781	−0.0833	0.094*
H10B	0.3390	0.6392	−0.0163	0.094*
H10C	0.1367	0.6281	0.0048	0.094*
C11	0.4309 (4)	0.3741 (2)	0.20165 (15)	0.0544 (6)
C12	0.5466 (4)	0.2942 (2)	0.24460 (18)	0.0742 (9)
H12	0.5584	0.2297	0.2162	0.089*
C13	0.6456 (4)	0.3073 (2)	0.32874 (18)	0.0729 (8)
H13	0.7257	0.2532	0.3561	0.087*
C14	0.6243 (4)	0.4007 (2)	0.37115 (16)	0.0589 (7)
C15	0.5060 (4)	0.4801 (2)	0.33155 (17)	0.0704 (8)
H15	0.4903	0.5429	0.3613	0.085*
C16	0.4093 (4)	0.4668 (2)	0.24666 (17)	0.0679 (8)
H16	0.3289	0.5211	0.2198	0.081*
Cl1	0.74755 (12)	0.41813 (6)	0.47717 (5)	0.0868 (3)
N1	0.3387 (3)	0.35391 (18)	0.11479 (13)	0.0642 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0509 (15)	0.0545 (15)	0.0543 (15)	−0.0032 (12)	0.0145 (12)	−0.0052 (12)
C2	0.0647 (18)	0.0620 (17)	0.0567 (16)	−0.0099 (13)	0.0161 (13)	−0.0195 (13)
C3	0.0560 (16)	0.0773 (19)	0.0477 (14)	−0.0106 (14)	0.0076 (12)	−0.0068 (14)
C4	0.0553 (16)	0.0606 (16)	0.0514 (15)	−0.0046 (13)	0.0042 (12)	0.0065 (12)
C5	0.0395 (13)	0.0540 (15)	0.0532 (14)	−0.0032 (11)	0.0097 (11)	−0.0038 (11)
C6	0.0386 (13)	0.0526 (14)	0.0451 (13)	−0.0037 (11)	0.0113 (10)	−0.0036 (11)
C7	0.0478 (14)	0.0525 (15)	0.0507 (14)	−0.0031 (12)	0.0097 (11)	−0.0070 (12)
C8	0.102 (2)	0.0502 (16)	0.0739 (19)	0.0005 (15)	0.0191 (17)	−0.0075 (13)
C9	0.098 (2)	0.118 (3)	0.0494 (16)	−0.013 (2)	0.0029 (16)	−0.0095 (17)
C10	0.0644 (18)	0.0555 (16)	0.0653 (17)	0.0012 (13)	0.0087 (13)	−0.0035 (13)
C11	0.0577 (16)	0.0568 (15)	0.0468 (14)	−0.0031 (13)	0.0067 (12)	0.0032 (12)
C12	0.109 (2)	0.0492 (15)	0.0595 (17)	0.0074 (16)	0.0064 (16)	0.0013 (13)
C13	0.091 (2)	0.0588 (17)	0.0618 (17)	0.0151 (16)	−0.0005 (16)	0.0133 (14)
C14	0.0611 (17)	0.0606 (17)	0.0495 (15)	−0.0013 (13)	−0.0004 (12)	0.0066 (12)
C15	0.087 (2)	0.0643 (18)	0.0535 (16)	0.0166 (16)	0.0004 (15)	−0.0049 (13)
C16	0.075 (2)	0.0669 (18)	0.0560 (16)	0.0206 (15)	0.0018 (14)	0.0017 (14)
Cl1	0.1009 (7)	0.0845 (6)	0.0590 (5)	−0.0013 (5)	−0.0189 (4)	0.0027 (4)
N1	0.0795 (16)	0.0600 (14)	0.0491 (12)	−0.0032 (12)	0.0049 (11)	0.0004 (11)

Geometric parameters (Å, º) top

C1—C2	1.386 (3)	C9—H9B	0.9600
C1—C6	1.419 (3)	C9—H9C	0.9600
C1—C8	1.506 (3)	C10—H10A	0.9600
C2—C3	1.380 (4)	C10—H10B	0.9600
C2—H2	0.9300	C10—H10C	0.9600
C3—C4	1.379 (3)	C11—C12	1.378 (4)
C3—C9	1.520 (3)	C11—C16	1.379 (3)
C4—C5	1.391 (3)	C11—N1	1.419 (3)
C4—H4	0.9300	C12—C13	1.382 (4)
C5—C6	1.408 (3)	C12—H12	0.9300
C5—C10	1.513 (3)	C13—C14	1.364 (4)
C6—C7	1.469 (3)	C13—H13	0.9300
C7—N1	1.254 (3)	C14—C15	1.365 (4)
C7—H7	0.9300	C14—Cl1	1.740 (3)
C8—H8A	0.9600	C15—C16	1.388 (4)
C8—H8B	0.9600	C15—H15	0.9300
C8—H8C	0.9600	C16—H16	0.9300
C9—H9A	0.9600

C2—C1—C6	118.4 (2)	H9A—C9—H9B	109.5
C2—C1—C8	118.1 (2)	C3—C9—H9C	109.5
C6—C1—C8	123.5 (2)	H9A—C9—H9C	109.5
C3—C2—C1	123.1 (2)	H9B—C9—H9C	109.5
C3—C2—H2	118.5	C5—C10—H10A	109.5
C1—C2—H2	118.5	C5—C10—H10B	109.5
C4—C3—C2	117.8 (2)	H10A—C10—H10B	109.5
C4—C3—C9	121.3 (3)	C5—C10—H10C	109.5
C2—C3—C9	120.8 (2)	H10A—C10—H10C	109.5
C3—C4—C5	122.2 (2)	H10B—C10—H10C	109.5
C3—C4—H4	118.9	C12—C11—C16	117.8 (2)
C5—C4—H4	118.9	C12—C11—N1	117.5 (2)
C4—C5—C6	119.3 (2)	C16—C11—N1	124.7 (2)
C4—C5—C10	118.3 (2)	C11—C12—C13	121.7 (3)
C6—C5—C10	122.4 (2)	C11—C12—H12	119.1
C5—C6—C1	119.2 (2)	C13—C12—H12	119.1
C5—C6—C7	118.4 (2)	C14—C13—C12	119.2 (2)
C1—C6—C7	122.3 (2)	C14—C13—H13	120.4
N1—C7—C6	125.9 (2)	C12—C13—H13	120.4
N1—C7—H7	117.0	C13—C14—C15	120.7 (2)
C6—C7—H7	117.0	C13—C14—Cl1	119.7 (2)
C1—C8—H8A	109.5	C15—C14—Cl1	119.7 (2)
C1—C8—H8B	109.5	C14—C15—C16	119.7 (3)
H8A—C8—H8B	109.5	C14—C15—H15	120.1
C1—C8—H8C	109.5	C16—C15—H15	120.1
H8A—C8—H8C	109.5	C11—C16—C15	120.9 (3)
H8B—C8—H8C	109.5	C11—C16—H16	119.6
C3—C9—H9A	109.5	C15—C16—H16	119.6
C3—C9—H9B	109.5	C7—N1—C11	119.9 (2)

C6—C1—C2—C3	0.0 (4)	C5—C6—C7—N1	169.1 (2)
C8—C1—C2—C3	179.8 (2)	C1—C6—C7—N1	−14.4 (4)
C1—C2—C3—C4	−0.8 (4)	C16—C11—C12—C13	−2.9 (4)
C1—C2—C3—C9	179.4 (2)	N1—C11—C12—C13	178.6 (3)
C2—C3—C4—C5	1.2 (4)	C11—C12—C13—C14	1.8 (5)
C9—C3—C4—C5	−179.0 (2)	C12—C13—C14—C15	0.4 (4)
C3—C4—C5—C6	−0.7 (4)	C12—C13—C14—Cl1	179.8 (2)
C3—C4—C5—C10	−179.8 (2)	C13—C14—C15—C16	−1.3 (4)
C4—C5—C6—C1	−0.2 (3)	Cl1—C14—C15—C16	179.3 (2)
C10—C5—C6—C1	178.9 (2)	C12—C11—C16—C15	2.0 (4)
C4—C5—C6—C7	176.4 (2)	N1—C11—C16—C15	−179.6 (3)
C10—C5—C6—C7	−4.5 (3)	C14—C15—C16—C11	0.1 (5)
C2—C1—C6—C5	0.5 (3)	C6—C7—N1—C11	176.6 (2)
C8—C1—C6—C5	−179.3 (2)	C12—C11—N1—C7	−143.8 (3)
C2—C1—C6—C7	−176.0 (2)	C16—C11—N1—C7	37.8 (4)
C8—C1—C6—C7	4.2 (4)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆ClN
M_r	257.75
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.198 (2), 12.398 (4), 15.865 (5)
β (°)	102.296 (4)
V (Å³)	1383.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.31 × 0.30 × 0.29

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.924, 0.929
No. of measured, independent and observed [I > 2σ(I)] reflections	7071, 2553, 1593
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.136, 1.04
No. of reflections	2553
No. of parameters	167
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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

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