N-[(E)-4-Chloro-benzyl-idene]-2,4-dimethyl-aniline.

The title mol-ecule, C(15)H(14)ClN, exists in a trans configuration with respect to the C=N bond [1.2813 (16) Å]. The dihedral angle between the benzene rings is 52.91 (6)°. The crystal structure is stabilized by weak inter-molecular C-H⋯π inter-actions.

Related literature

For general background to and the pharmacological activity of Schiff base compounds, see: Ittel et al. (2000 ▶); Shah et al. (1992 ▶); Cimerman et al. (2000 ▶); Pandeya et al. (1999 ▶); More et al. (2001 ▶); Cimerman & Stefanac (2001 ▶); Galic et al. (1997 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H14ClN

M = 243.72

Monoclinic,

a = 7.2852 (1) Å

b = 15.2715 (2) Å

c = 11.5382 (1) Å

β = 96.304 (1)°

V = 1275.93 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 100 K

0.40 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.898, T max = 0.946

14547 measured reflections

3975 independent reflections

3800 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.078

S = 1.04

3975 reflections

156 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1919 Friedel pairs

Flack parameter: 0.04 (4)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAIn class="Chemical">NT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026109/lh5274sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026109/lh5274Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026109/lh5274Isup3.cml

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

C15H14ClN	F(000) = 512
Mr = 243.72	Dx = 1.269 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 9896 reflections
a = 7.2852 (1) Å	θ = 2.7–31.0°
b = 15.2715 (2) Å	µ = 0.28 mm−1
c = 11.5382 (1) Å	T = 100 K
β = 96.304 (1)°	Block, colourless
V = 1275.93 (3) Å3	0.40 × 0.24 × 0.20 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3975 independent reflections
Radiation source: fine-focus sealed tube	3800 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 31.1°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.898, Tmax = 0.946	k = −17→22
14547 measured reflections	l = −16→16

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)] = 0.031	H-atom parameters constrained
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0435P)2 + 0.4511P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3975 reflections	Δρmax = 0.32 e Å−3
156 parameters	Δρmin = −0.20 e Å−3
2 restraints	Absolute structure: Flack (1983), 1919 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (4)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	1.00011 (4)	0.620805 (19)	0.24699 (3)	0.02374 (8)
N1	0.98639 (15)	0.21574 (7)	0.00510 (9)	0.0164 (2)
C1	1.10819 (17)	0.36449 (8)	0.25068 (11)	0.0164 (2)
H1A	1.1660	0.3226	0.3036	0.020*
C2	1.09740 (18)	0.45134 (9)	0.28532 (11)	0.0174 (2)
H2A	1.1469	0.4693	0.3612	0.021*
C3	1.01230 (18)	0.51134 (8)	0.20614 (11)	0.0172 (2)
C4	0.93749 (17)	0.48677 (9)	0.09481 (11)	0.0180 (2)
H4A	0.8786	0.5288	0.0425	0.022*
C5	0.95032 (17)	0.39987 (8)	0.06141 (11)	0.0166 (2)
H5A	0.9011	0.3823	−0.0147	0.020*
C6	1.03527 (17)	0.33777 (8)	0.13907 (11)	0.0152 (2)
C7	1.04654 (18)	0.24507 (8)	0.10622 (11)	0.0163 (2)
H7A	1.1011	0.2049	0.1628	0.020*
C8	0.99097 (17)	0.12365 (8)	−0.01051 (11)	0.0153 (2)
C9	1.05963 (17)	0.08957 (8)	−0.11026 (11)	0.0151 (2)
C10	1.05936 (17)	−0.00135 (8)	−0.12576 (11)	0.0164 (2)
H10A	1.1084	−0.0250	−0.1920	0.020*
C11	0.98889 (18)	−0.05863 (8)	−0.04642 (11)	0.0177 (2)
C12	0.91927 (18)	−0.02310 (9)	0.05076 (11)	0.0182 (2)
H12A	0.8702	−0.0608	0.1052	0.022*
C13	0.92063 (18)	0.06723 (8)	0.06920 (11)	0.0172 (2)
H13A	0.8735	0.0905	0.1363	0.021*
C14	1.1312 (2)	0.14980 (9)	−0.19821 (12)	0.0212 (3)
H14A	1.1739	0.1151	−0.2615	0.032*
H14B	1.2342	0.1844	−0.1603	0.032*
H14C	1.0321	0.1892	−0.2301	0.032*
C15	0.9863 (2)	−0.15650 (9)	−0.06663 (13)	0.0244 (3)
H15A	0.8998	−0.1840	−0.0183	0.037*
H15B	1.1104	−0.1803	−0.0457	0.037*
H15C	0.9469	−0.1686	−0.1490	0.037*

	U11	U22	U33	U12	U13	U23
Cl1	0.03157 (16)	0.01487 (12)	0.02478 (15)	0.00105 (13)	0.00319 (11)	−0.00480 (12)
N1	0.0188 (5)	0.0143 (5)	0.0163 (5)	−0.0001 (4)	0.0033 (4)	−0.0014 (4)
C1	0.0181 (6)	0.0165 (5)	0.0144 (5)	−0.0008 (4)	0.0007 (4)	−0.0001 (4)
C2	0.0194 (6)	0.0181 (5)	0.0144 (5)	−0.0012 (5)	0.0011 (4)	−0.0029 (4)
C3	0.0189 (6)	0.0133 (5)	0.0198 (6)	−0.0009 (4)	0.0045 (5)	−0.0034 (4)
C4	0.0188 (6)	0.0163 (6)	0.0187 (6)	0.0012 (4)	0.0010 (4)	0.0005 (4)
C5	0.0187 (6)	0.0161 (5)	0.0149 (5)	0.0001 (4)	0.0015 (4)	−0.0014 (4)
C6	0.0159 (5)	0.0141 (5)	0.0157 (5)	−0.0004 (4)	0.0025 (4)	−0.0017 (4)
C7	0.0168 (5)	0.0145 (5)	0.0178 (5)	0.0002 (4)	0.0024 (4)	−0.0004 (4)
C8	0.0162 (5)	0.0134 (5)	0.0160 (6)	−0.0001 (4)	0.0009 (4)	−0.0009 (4)
C9	0.0164 (5)	0.0149 (5)	0.0138 (5)	−0.0010 (4)	0.0011 (4)	−0.0012 (4)
C10	0.0178 (5)	0.0160 (5)	0.0155 (5)	0.0003 (4)	0.0016 (4)	−0.0025 (4)
C11	0.0185 (6)	0.0146 (5)	0.0191 (6)	−0.0012 (5)	−0.0019 (5)	−0.0005 (4)
C12	0.0198 (6)	0.0168 (6)	0.0180 (6)	−0.0029 (5)	0.0011 (5)	0.0026 (4)
C13	0.0204 (6)	0.0173 (6)	0.0141 (5)	−0.0008 (5)	0.0024 (4)	−0.0005 (4)
C14	0.0272 (7)	0.0173 (6)	0.0205 (6)	−0.0027 (5)	0.0088 (5)	−0.0008 (5)
C15	0.0305 (7)	0.0135 (6)	0.0284 (7)	−0.0016 (5)	−0.0005 (6)	−0.0020 (5)

Cl1—C3	1.7418 (13)	C8—C9	1.4043 (17)
N1—C7	1.2813 (16)	C9—C10	1.3999 (17)
N1—C8	1.4187 (15)	C9—C14	1.5045 (18)
C1—C2	1.3900 (17)	C10—C11	1.4036 (18)
C1—C6	1.3988 (17)	C10—H10A	0.9500
C1—H1A	0.9500	C11—C12	1.3906 (19)
C2—C3	1.3908 (18)	C11—C15	1.5125 (18)
C2—H2A	0.9500	C12—C13	1.3957 (18)
C3—C4	1.3906 (17)	C12—H12A	0.9500
C4—C5	1.3881 (18)	C13—H13A	0.9500
C4—H4A	0.9500	C14—H14A	0.9800
C5—C6	1.4012 (17)	C14—H14B	0.9800
C5—H5A	0.9500	C14—H14C	0.9800
C6—C7	1.4702 (17)	C15—H15A	0.9800
C7—H7A	0.9500	C15—H15B	0.9800
C8—C13	1.3980 (18)	C15—H15C	0.9800
C7—N1—C8	116.85 (11)	C10—C9—C14	121.06 (11)
C2—C1—C6	121.02 (12)	C8—C9—C14	120.48 (11)
C2—C1—H1A	119.5	C9—C10—C11	122.03 (12)
C6—C1—H1A	119.5	C9—C10—H10A	119.0
C1—C2—C3	118.36 (11)	C11—C10—H10A	119.0
C1—C2—H2A	120.8	C12—C11—C10	118.34 (12)
C3—C2—H2A	120.8	C12—C11—C15	120.68 (12)
C4—C3—C2	122.02 (12)	C10—C11—C15	120.98 (12)
C4—C3—Cl1	118.84 (10)	C11—C12—C13	120.76 (12)
C2—C3—Cl1	119.13 (10)	C11—C12—H12A	119.6
C5—C4—C3	118.88 (12)	C13—C12—H12A	119.6
C5—C4—H4A	120.6	C12—C13—C8	120.39 (12)
C3—C4—H4A	120.6	C12—C13—H13A	119.8
C4—C5—C6	120.52 (11)	C8—C13—H13A	119.8
C4—C5—H5A	119.7	C9—C14—H14A	109.5
C6—C5—H5A	119.7	C9—C14—H14B	109.5
C1—C6—C5	119.20 (11)	H14A—C14—H14B	109.5
C1—C6—C7	119.47 (11)	C9—C14—H14C	109.5
C5—C6—C7	121.33 (11)	H14A—C14—H14C	109.5
N1—C7—C6	123.24 (12)	H14B—C14—H14C	109.5
N1—C7—H7A	118.4	C11—C15—H15A	109.5
C6—C7—H7A	118.4	C11—C15—H15B	109.5
C13—C8—C9	120.00 (11)	H15A—C15—H15B	109.5
C13—C8—N1	120.80 (12)	C11—C15—H15C	109.5
C9—C8—N1	119.14 (11)	H15A—C15—H15C	109.5
C10—C9—C8	118.47 (11)	H15B—C15—H15C	109.5
C6—C1—C2—C3	−0.07 (19)	C7—N1—C8—C9	−133.76 (13)
C1—C2—C3—C4	0.46 (19)	C13—C8—C9—C10	−1.42 (18)
C1—C2—C3—Cl1	−179.11 (10)	N1—C8—C9—C10	−178.57 (11)
C2—C3—C4—C5	−0.81 (19)	C13—C8—C9—C14	178.43 (12)
Cl1—C3—C4—C5	178.77 (10)	N1—C8—C9—C14	1.29 (18)
C3—C4—C5—C6	0.76 (19)	C8—C9—C10—C11	1.54 (18)
C2—C1—C6—C5	0.04 (19)	C14—C9—C10—C11	−178.31 (12)
C2—C1—C6—C7	−178.99 (12)	C9—C10—C11—C12	−0.63 (19)
C4—C5—C6—C1	−0.39 (19)	C9—C10—C11—C15	178.60 (11)
C4—C5—C6—C7	178.62 (12)	C10—C11—C12—C13	−0.40 (18)
C8—N1—C7—C6	−174.26 (12)	C15—C11—C12—C13	−179.64 (13)
C1—C6—C7—N1	−178.57 (12)	C11—C12—C13—C8	0.50 (19)
C5—C6—C7—N1	2.4 (2)	C9—C8—C13—C12	0.44 (19)
C7—N1—C8—C13	49.12 (17)	N1—C8—C13—C12	177.53 (12)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···Cg1i	0.95	2.67	3.3885 (14)	132
C14—H14A···Cg1ii	0.98	2.86	3.4853 (14)	124
C2—H2A···Cg2iii	0.95	2.73	3.4371 (14)	132
C4—H4A···Cg2iv	0.95	2.80	3.5534 (15)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯Cg1i	0.95	2.67	3.3885 (14)	132
C14—H14A⋯Cg1ii	0.98	2.86	3.4853 (14)	124
C2—H2A⋯Cg2iii	0.95	2.73	3.4371 (14)	132
C4—H4A⋯Cg2iv	0.95	2.80	3.5534 (15)	134

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .