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

In the title mol-ecule, C(15)H(15)ClN(2), the dihedral angle between the aromatic is 64.1 (2)°.

Related literature

For a related compound, see: You et al. (2004 ▶).

Experimental

Crystal data

C15H15ClN2

M = 258.74

Orthorhombic,

a = 7.7301 (8) Å

b = 12.2016 (18) Å

c = 14.047 (2) Å

V = 1325.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 298 (2) K

0.45 × 0.38 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.888, T max = 0.923

5507 measured reflections

2318 independent reflections

1391 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.105

S = 1.02

2318 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1358 Friedel pairs

Flack parameter: −0.07 (10)

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536808036386/lh2690sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036386/lh2690Isup2.hkl

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

C15H15ClN2	F000 = 544
Mr = 258.74	Dx = 1.297 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1182 reflections
a = 7.7301 (8) Å	θ = 2.9–20.1º
b = 12.2016 (18) Å	µ = 0.27 mm−1
c = 14.047 (2) Å	T = 298 (2) K
V = 1325.0 (3) Å3	Block, light yellow
Z = 4	0.45 × 0.38 × 0.30 mm

Bruker SMART CCD diffractometer	2318 independent reflections
Radiation source: fine-focus sealed tube	1391 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.054
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Bruker, 1997)	h = −9→9
Tmin = 0.888, Tmax = 0.923	k = −14→13
5507 measured reflections	l = −9→16

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045	w = 1/[σ2(Fo2) + (0.0377P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.105	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.18 e Å−3
2318 reflections	Δρmin = −0.18 e Å−3
165 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1358 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.07 (10)

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
Cl1	1.22788 (14)	1.11816 (8)	−0.13149 (7)	0.0753 (4)
N1	0.9918 (4)	0.9322 (2)	−0.09661 (18)	0.0513 (8)
N2	0.8770 (4)	0.7449 (2)	0.32629 (18)	0.0555 (8)
C1	1.0238 (4)	0.8391 (3)	−0.0595 (2)	0.0477 (9)
H1	1.0788	0.7861	−0.0962	0.057*
C2	0.9776 (4)	0.8127 (2)	0.0381 (2)	0.0436 (9)
C3	0.8837 (4)	0.8839 (3)	0.0949 (2)	0.0460 (9)
H3	0.8439	0.9491	0.0686	0.055*
C4	0.8472 (5)	0.8618 (3)	0.1884 (2)	0.0478 (9)
H4	0.7815	0.9112	0.2235	0.057*
C5	0.9077 (4)	0.7656 (3)	0.2319 (2)	0.0441 (9)
C6	0.9993 (5)	0.6920 (3)	0.1744 (2)	0.0498 (9)
H6	1.0379	0.6261	0.2002	0.060*
C7	1.0331 (5)	0.7156 (3)	0.0807 (2)	0.0510 (10)
H7	1.0949	0.6652	0.0445	0.061*
C8	0.7854 (5)	0.8221 (3)	0.3849 (2)	0.0719 (12)
H8A	0.8528	0.8878	0.3913	0.108*
H8B	0.7660	0.7908	0.4467	0.108*
H8C	0.6763	0.8394	0.3559	0.108*
C9	0.9648 (5)	0.6548 (3)	0.3736 (2)	0.0671 (11)
H9A	0.9342	0.5870	0.3432	0.101*
H9B	0.9305	0.6524	0.4393	0.101*
H9C	1.0876	0.6654	0.3696	0.101*
C10	1.0315 (5)	0.9502 (3)	−0.1928 (2)	0.0452 (9)
C11	1.1315 (4)	1.0405 (3)	−0.2197 (2)	0.0481 (9)
C12	1.1594 (5)	1.0664 (3)	−0.3137 (2)	0.0595 (10)
H12	1.2266	1.1269	−0.3298	0.071*
C13	1.0873 (5)	1.0020 (3)	−0.3841 (3)	0.0654 (11)
H13	1.1042	1.0197	−0.4478	0.078*
C14	0.9911 (5)	0.9125 (3)	−0.3600 (3)	0.0661 (11)
H14	0.9451	0.8682	−0.4075	0.079*
C15	0.9612 (5)	0.8869 (3)	−0.2650 (2)	0.0587 (10)
H15	0.8932	0.8266	−0.2497	0.070*

	U11	U22	U33	U12	U13	U23
Cl1	0.0818 (8)	0.0730 (7)	0.0711 (6)	−0.0204 (6)	−0.0003 (6)	−0.0069 (5)
N1	0.060 (2)	0.0516 (17)	0.0423 (16)	−0.0012 (18)	0.0060 (16)	0.0035 (14)
N2	0.053 (2)	0.069 (2)	0.0440 (17)	0.0048 (18)	0.0025 (15)	0.0064 (15)
C1	0.048 (3)	0.050 (2)	0.045 (2)	−0.0014 (19)	−0.0003 (19)	−0.0074 (17)
C2	0.046 (2)	0.0450 (19)	0.0397 (19)	−0.0033 (19)	0.0012 (18)	−0.0035 (16)
C3	0.049 (2)	0.0394 (18)	0.049 (2)	0.0003 (19)	−0.0047 (17)	0.0001 (18)
C4	0.050 (2)	0.048 (2)	0.045 (2)	0.0075 (17)	0.0021 (18)	−0.0034 (17)
C5	0.042 (2)	0.052 (2)	0.0386 (19)	−0.0057 (18)	−0.0011 (17)	−0.0029 (18)
C6	0.057 (3)	0.0407 (19)	0.051 (2)	0.005 (2)	−0.003 (2)	0.0055 (17)
C7	0.056 (3)	0.049 (2)	0.048 (2)	0.0044 (19)	0.0023 (19)	−0.0053 (18)
C8	0.076 (3)	0.095 (3)	0.045 (2)	0.004 (3)	0.012 (2)	−0.002 (2)
C9	0.062 (3)	0.078 (3)	0.061 (2)	−0.007 (2)	−0.004 (2)	0.024 (2)
C10	0.047 (2)	0.046 (2)	0.043 (2)	0.0044 (19)	0.0025 (19)	0.0001 (17)
C11	0.047 (2)	0.050 (2)	0.047 (2)	0.0046 (19)	0.0041 (19)	0.0020 (17)
C12	0.058 (3)	0.063 (2)	0.058 (2)	−0.002 (2)	0.014 (2)	0.009 (2)
C13	0.069 (3)	0.081 (3)	0.046 (2)	0.019 (2)	0.008 (2)	0.008 (2)
C14	0.068 (3)	0.080 (3)	0.050 (2)	0.007 (3)	−0.006 (2)	−0.007 (2)
C15	0.062 (3)	0.057 (2)	0.057 (2)	−0.003 (2)	0.000 (2)	−0.001 (2)

Cl1—C11	1.728 (3)	C7—H7	0.9300
N1—C1	1.274 (3)	C8—H8A	0.9600
N1—C10	1.403 (4)	C8—H8B	0.9600
N2—C5	1.371 (4)	C8—H8C	0.9600
N2—C8	1.438 (4)	C9—H9A	0.9600
N2—C9	1.453 (4)	C9—H9B	0.9600
C1—C2	1.453 (4)	C9—H9C	0.9600
C1—H1	0.9300	C10—C15	1.385 (4)
C2—C3	1.385 (4)	C10—C11	1.398 (4)
C2—C7	1.395 (4)	C11—C12	1.376 (4)
C3—C4	1.369 (4)	C12—C13	1.379 (5)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.404 (4)	C13—C14	1.364 (5)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.400 (4)	C14—C15	1.390 (4)
C6—C7	1.373 (4)	C14—H14	0.9300
C6—H6	0.9300	C15—H15	0.9300
?···?	?
C1—N1—C10	119.4 (3)	N2—C8—H8C	109.5
C5—N2—C8	121.2 (3)	H8A—C8—H8C	109.5
C5—N2—C9	120.1 (3)	H8B—C8—H8C	109.5
C8—N2—C9	117.6 (3)	N2—C9—H9A	109.5
N1—C1—C2	122.5 (3)	N2—C9—H9B	109.5
N1—C1—H1	118.8	H9A—C9—H9B	109.5
C2—C1—H1	118.8	N2—C9—H9C	109.5
C3—C2—C7	116.5 (3)	H9A—C9—H9C	109.5
C3—C2—C1	122.2 (3)	H9B—C9—H9C	109.5
C7—C2—C1	121.2 (3)	C15—C10—C11	117.3 (3)
C4—C3—C2	122.5 (3)	C15—C10—N1	122.2 (3)
C4—C3—H3	118.7	C11—C10—N1	120.2 (3)
C2—C3—H3	118.7	C12—C11—C10	121.8 (3)
C3—C4—C5	120.9 (3)	C12—C11—Cl1	119.7 (3)
C3—C4—H4	119.6	C10—C11—Cl1	118.5 (3)
C5—C4—H4	119.6	C11—C12—C13	119.6 (3)
N2—C5—C6	121.8 (3)	C11—C12—H12	120.2
N2—C5—C4	121.2 (3)	C13—C12—H12	120.2
C6—C5—C4	117.0 (3)	C14—C13—C12	119.9 (3)
C7—C6—C5	121.0 (3)	C14—C13—H13	120.0
C7—C6—H6	119.5	C12—C13—H13	120.0
C5—C6—H6	119.5	C13—C14—C15	120.6 (4)
C6—C7—C2	122.1 (3)	C13—C14—H14	119.7
C6—C7—H7	119.0	C15—C14—H14	119.7
C2—C7—H7	119.0	C10—C15—C14	120.8 (3)
N2—C8—H8A	109.5	C10—C15—H15	119.6
N2—C8—H8B	109.5	C14—C15—H15	119.6
H8A—C8—H8B	109.5
C10—N1—C1—C2	−176.5 (3)	C3—C2—C7—C6	−1.0 (5)
N1—C1—C2—C3	5.2 (5)	C1—C2—C7—C6	176.2 (3)
N1—C1—C2—C7	−171.9 (3)	C1—N1—C10—C15	58.8 (5)
C7—C2—C3—C4	0.5 (5)	C1—N1—C10—C11	−127.5 (4)
C1—C2—C3—C4	−176.7 (3)	C15—C10—C11—C12	0.1 (5)
C2—C3—C4—C5	1.4 (5)	N1—C10—C11—C12	−173.9 (3)
C8—N2—C5—C6	178.9 (3)	C15—C10—C11—Cl1	−177.6 (2)
C9—N2—C5—C6	10.8 (5)	N1—C10—C11—Cl1	8.4 (4)
C8—N2—C5—C4	−1.6 (5)	C10—C11—C12—C13	0.1 (5)
C9—N2—C5—C4	−169.6 (3)	Cl1—C11—C12—C13	177.7 (3)
C3—C4—C5—N2	177.6 (3)	C11—C12—C13—C14	−1.0 (6)
C3—C4—C5—C6	−2.8 (5)	C12—C13—C14—C15	1.6 (6)
N2—C5—C6—C7	−178.1 (3)	C11—C10—C15—C14	0.6 (5)
C4—C5—C6—C7	2.3 (5)	N1—C10—C15—C14	174.4 (3)
C5—C6—C7—C2	−0.4 (5)	C13—C14—C15—C10	−1.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
?—?···?	?	?	?	?