(E)-4-Chloro-N-(2,4,6-trimethyl-benzyl-idene)aniline.

In the title compound, C(16)H(16)ClN, the dihedral angle between the benzene rings is 24.61 (13)°. In the crystal, only van der Waals inter-actions occur between neighbouring mol-ecules.

Related literature

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

Experimental

Crystal data

C16H16ClN

M = 257.75

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 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 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811027024/hb5944sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811027024/hb5944Isup3.cml

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

C16H16ClN	F(000) = 544
Mr = 257.75	Dx = 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

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

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(Fo2) + (0.0476P)2 + 0.5504P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2553 reflections	Δρmax = 0.19 e Å−3
167 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)