N-[(E)-4-Chloro-benzyl-idene]-N'-phenyl-benzene-1,4-diamine.

The title compound, C(19)H(15)ClN(2), adopts an E configuration with respect to the position of the chloro-benzene and diphenyl-amine groups on the C=N azomethine bond. The mol-ecule is not planar, the central six-membered ring making angles of 12.26 (10) and 44.18 (11)° with the 4-chloro-phenyl and phenyl rings, respectively. In the crystal structure, weak C-H⋯π inter-actions contribute to the stabilization of the packing.

Related literature

For related structures, see: Ojala et al. (2007 ▶); Fun et al. (2008 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For the biological activity of Schiff bases, see: Küstü et al. (2007 ▶) and for their pharmaceutical properties and applications as corrosion inhibitors, see: Singh & Dhakarey (2009 ▶).

Experimental

Crystal data

C19H15ClN2

M = 306.78

Monoclinic,

a = 10.3353 (15) Å

b = 17.045 (3) Å

c = 8.7893 (13) Å

β = 97.384 (3)°

V = 1535.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 298 K

0.50 × 0.39 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.886, T max = 0.971

8939 measured reflections

2860 independent reflections

2076 reflections with I > 2/s(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.127

S = 1.05

2860 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002742X/zq2049sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002742X/zq2049Isup2.hkl

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

C19H15ClN2	F(000) = 640
Mr = 306.78	Dx = 1.327 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1956 reflections
a = 10.3353 (15) Å	θ = 1.9–25.5°
b = 17.045 (3) Å	µ = 0.25 mm−1
c = 8.7893 (13) Å	T = 298 K
β = 97.384 (3)°	Block, colourless
V = 1535.5 (4) Å3	0.50 × 0.39 × 0.12 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2860 independent reflections
Radiation source: fine-focus sealed tube	2076 reflections with I > 2/s(I)
graphite	Rint = 0.038
Detector resolution: 83.66 pixels mm-1	θmax = 25.5°, θmin = 1.9°
ω scan	h = −11→12
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −14→20
Tmin = 0.886, Tmax = 0.971	l = −10→9
8939 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.388P] where P = (Fo2 + 2Fc2)/3
2860 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.27 e Å−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
Cl1	0.49291 (8)	0.14092 (4)	1.51538 (8)	0.0878 (3)
N1	0.19891 (17)	0.12993 (11)	0.7853 (2)	0.0563 (5)
N2	−0.00657 (18)	0.08239 (12)	0.1689 (2)	0.0649 (6)
H2A	0.0363	0.0492	0.1212	0.078*
C1	0.3831 (2)	0.03701 (13)	1.1159 (3)	0.0595 (6)
H1B	0.3918	−0.0123	1.0730	0.071*
C2	0.4384 (2)	0.05077 (14)	1.2645 (3)	0.0614 (6)
H2B	0.4851	0.0116	1.3210	0.074*
C3	0.4233 (2)	0.12328 (14)	1.3281 (3)	0.0568 (6)
C4	0.3532 (2)	0.18165 (13)	1.2465 (3)	0.0583 (6)
H4A	0.3421	0.2301	1.2915	0.070*
C5	0.2997 (2)	0.16732 (13)	1.0975 (3)	0.0540 (6)
H5A	0.2526	0.2067	1.0418	0.065*
C6	0.3150 (2)	0.09492 (13)	1.0290 (2)	0.0502 (5)
C7	0.2607 (2)	0.07919 (13)	0.8699 (3)	0.0556 (6)
H7A	0.2723	0.0296	0.8296	0.067*
C8	0.1486 (2)	0.11346 (13)	0.6310 (2)	0.0506 (5)
C9	0.0617 (2)	0.16743 (13)	0.5585 (3)	0.0565 (6)
H9A	0.0388	0.2110	0.6130	0.068*
C10	0.0079 (2)	0.15853 (13)	0.4074 (3)	0.0574 (6)
H10A	−0.0497	0.1960	0.3615	0.069*
C11	0.0396 (2)	0.09396 (13)	0.3239 (3)	0.0514 (5)
C12	0.1269 (2)	0.03969 (14)	0.3963 (3)	0.0575 (6)
H12A	0.1493	−0.0040	0.3418	0.069*
C13	0.1808 (2)	0.04887 (13)	0.5455 (3)	0.0561 (6)
H13A	0.2395	0.0117	0.5907	0.067*
C14	−0.1137 (2)	0.11789 (12)	0.0811 (3)	0.0500 (5)
C15	−0.2251 (2)	0.13990 (12)	0.1426 (3)	0.0532 (6)
H15A	−0.2297	0.1331	0.2468	0.064*
C16	−0.3291 (2)	0.17186 (13)	0.0496 (3)	0.0581 (6)
H16A	−0.4032	0.1871	0.0920	0.070*
C17	−0.3251 (2)	0.18156 (14)	−0.1047 (3)	0.0649 (6)
H17A	−0.3957	0.2034	−0.1667	0.078*
C18	−0.2160 (3)	0.15871 (14)	−0.1662 (3)	0.0650 (6)
H18A	−0.2133	0.1642	−0.2710	0.078*
C19	−0.1107 (2)	0.12777 (14)	−0.0752 (3)	0.0592 (6)
H19A	−0.0368	0.1133	−0.1185	0.071*

	U11	U22	U33	U12	U13	U23
Cl1	0.1158 (6)	0.0755 (5)	0.0653 (4)	−0.0226 (4)	−0.0141 (4)	0.0041 (3)
N1	0.0524 (11)	0.0529 (11)	0.0630 (12)	0.0028 (9)	0.0051 (9)	−0.0015 (10)
N2	0.0588 (12)	0.0757 (14)	0.0600 (12)	0.0135 (10)	0.0066 (10)	−0.0130 (10)
C1	0.0701 (15)	0.0421 (12)	0.0673 (16)	0.0003 (11)	0.0133 (12)	0.0000 (11)
C2	0.0662 (15)	0.0529 (14)	0.0643 (15)	0.0013 (12)	0.0057 (12)	0.0133 (12)
C3	0.0604 (14)	0.0540 (14)	0.0555 (14)	−0.0116 (11)	0.0057 (11)	0.0039 (11)
C4	0.0668 (15)	0.0431 (13)	0.0659 (15)	−0.0022 (11)	0.0121 (12)	−0.0037 (11)
C5	0.0508 (13)	0.0477 (13)	0.0633 (14)	0.0054 (10)	0.0072 (11)	0.0043 (11)
C6	0.0457 (12)	0.0469 (13)	0.0594 (14)	−0.0024 (10)	0.0116 (10)	0.0018 (11)
C7	0.0589 (14)	0.0455 (13)	0.0628 (15)	−0.0044 (11)	0.0092 (11)	−0.0050 (11)
C8	0.0451 (12)	0.0494 (13)	0.0573 (14)	−0.0045 (10)	0.0066 (10)	−0.0005 (10)
C9	0.0581 (14)	0.0464 (13)	0.0653 (15)	0.0028 (11)	0.0083 (11)	−0.0064 (11)
C10	0.0578 (14)	0.0478 (13)	0.0645 (15)	0.0046 (11)	0.0005 (11)	0.0023 (11)
C11	0.0426 (12)	0.0540 (14)	0.0583 (14)	−0.0037 (10)	0.0091 (10)	−0.0028 (11)
C12	0.0481 (13)	0.0568 (14)	0.0677 (15)	0.0041 (11)	0.0082 (11)	−0.0126 (12)
C13	0.0460 (12)	0.0538 (14)	0.0681 (15)	0.0056 (11)	0.0056 (11)	−0.0019 (12)
C14	0.0481 (12)	0.0453 (12)	0.0562 (13)	−0.0049 (10)	0.0052 (10)	−0.0059 (10)
C15	0.0550 (13)	0.0522 (13)	0.0535 (13)	−0.0032 (11)	0.0119 (10)	−0.0031 (10)
C16	0.0528 (13)	0.0527 (14)	0.0691 (16)	0.0027 (11)	0.0087 (11)	−0.0079 (12)
C17	0.0684 (16)	0.0557 (14)	0.0676 (16)	0.0073 (12)	−0.0033 (13)	−0.0016 (12)
C18	0.0788 (17)	0.0640 (16)	0.0519 (14)	−0.0021 (13)	0.0072 (12)	−0.0003 (12)
C19	0.0574 (14)	0.0626 (15)	0.0603 (15)	−0.0054 (12)	0.0175 (11)	−0.0071 (12)

Cl1—C3	1.736 (2)	C9—C10	1.381 (3)
N1—C7	1.260 (3)	C9—H9A	0.9300
N1—C8	1.417 (3)	C10—C11	1.385 (3)
N2—C11	1.399 (3)	C10—H10A	0.9300
N2—C14	1.402 (3)	C11—C12	1.388 (3)
N2—H2A	0.8600	C12—C13	1.367 (3)
C1—C2	1.377 (3)	C12—H12A	0.9300
C1—C6	1.384 (3)	C13—H13A	0.9300
C1—H1B	0.9300	C14—C15	1.385 (3)
C2—C3	1.373 (3)	C14—C19	1.389 (3)
C2—H2B	0.9300	C15—C16	1.376 (3)
C3—C4	1.377 (3)	C15—H15A	0.9300
C4—C5	1.376 (3)	C16—C17	1.373 (3)
C4—H4A	0.9300	C16—H16A	0.9300
C5—C6	1.391 (3)	C17—C18	1.368 (3)
C5—H5A	0.9300	C17—H17A	0.9300
C6—C7	1.463 (3)	C18—C19	1.370 (3)
C7—H7A	0.9300	C18—H18A	0.9300
C8—C9	1.382 (3)	C19—H19A	0.9300
C8—C13	1.397 (3)
C7—N1—C8	121.7 (2)	C9—C10—C11	120.2 (2)
C11—N2—C14	128.39 (19)	C9—C10—H10A	119.9
C11—N2—H2A	115.8	C11—C10—H10A	119.9
C14—N2—H2A	115.8	C10—C11—C12	118.1 (2)
C2—C1—C6	121.4 (2)	C10—C11—N2	123.6 (2)
C2—C1—H1B	119.3	C12—C11—N2	118.2 (2)
C6—C1—H1B	119.3	C13—C12—C11	121.6 (2)
C3—C2—C1	119.0 (2)	C13—C12—H12A	119.2
C3—C2—H2B	120.5	C11—C12—H12A	119.2
C1—C2—H2B	120.5	C12—C13—C8	120.7 (2)
C2—C3—C4	121.2 (2)	C12—C13—H13A	119.6
C2—C3—Cl1	119.14 (19)	C8—C13—H13A	119.6
C4—C3—Cl1	119.66 (19)	C15—C14—C19	118.6 (2)
C5—C4—C3	119.2 (2)	C15—C14—N2	122.7 (2)
C5—C4—H4A	120.4	C19—C14—N2	118.7 (2)
C3—C4—H4A	120.4	C16—C15—C14	120.0 (2)
C4—C5—C6	121.0 (2)	C16—C15—H15A	120.0
C4—C5—H5A	119.5	C14—C15—H15A	120.0
C6—C5—H5A	119.5	C17—C16—C15	121.0 (2)
C1—C6—C5	118.2 (2)	C17—C16—H16A	119.5
C1—C6—C7	120.1 (2)	C15—C16—H16A	119.5
C5—C6—C7	121.7 (2)	C18—C17—C16	119.1 (2)
N1—C7—C6	122.8 (2)	C18—C17—H17A	120.4
N1—C7—H7A	118.6	C16—C17—H17A	120.4
C6—C7—H7A	118.6	C17—C18—C19	120.8 (2)
C9—C8—C13	117.5 (2)	C17—C18—H18A	119.6
C9—C8—N1	116.5 (2)	C19—C18—H18A	119.6
C13—C8—N1	126.0 (2)	C18—C19—C14	120.5 (2)
C10—C9—C8	121.8 (2)	C18—C19—H19A	119.8
C10—C9—H9A	119.1	C14—C19—H19A	119.8
C8—C9—H9A	119.1
C6—C1—C2—C3	1.1 (4)	C9—C10—C11—N2	−177.3 (2)
C1—C2—C3—C4	0.7 (4)	C14—N2—C11—C10	−18.4 (4)
C1—C2—C3—Cl1	−179.97 (17)	C14—N2—C11—C12	164.8 (2)
C2—C3—C4—C5	−1.4 (3)	C10—C11—C12—C13	0.1 (3)
Cl1—C3—C4—C5	179.28 (17)	N2—C11—C12—C13	177.0 (2)
C3—C4—C5—C6	0.3 (3)	C11—C12—C13—C8	0.5 (3)
C2—C1—C6—C5	−2.1 (3)	C9—C8—C13—C12	−0.5 (3)
C2—C1—C6—C7	178.2 (2)	N1—C8—C13—C12	−179.1 (2)
C4—C5—C6—C1	1.4 (3)	C11—N2—C14—C15	−32.5 (3)
C4—C5—C6—C7	−178.9 (2)	C11—N2—C14—C19	150.9 (2)
C8—N1—C7—C6	179.28 (18)	C19—C14—C15—C16	−0.9 (3)
C1—C6—C7—N1	−179.3 (2)	N2—C14—C15—C16	−177.6 (2)
C5—C6—C7—N1	1.0 (3)	C14—C15—C16—C17	0.8 (3)
C7—N1—C8—C9	167.8 (2)	C15—C16—C17—C18	0.2 (4)
C7—N1—C8—C13	−13.6 (3)	C16—C17—C18—C19	−1.2 (4)
C13—C8—C9—C10	0.1 (3)	C17—C18—C19—C14	1.0 (4)
N1—C8—C9—C10	178.8 (2)	C15—C14—C19—C18	0.0 (3)
C8—C9—C10—C11	0.5 (3)	N2—C14—C19—C18	176.8 (2)
C9—C10—C11—C12	−0.6 (3)

Cg1 and Cg3 are the centroids of the C1–C6 and C14–C19 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···Cg3i	0.93	2.95	3.661 (2)	135
C16—H16A···Cg1ii	0.93	2.90	3.624 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg3 are the centroids of the C1–C6 and C14–C19 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯Cg3i	0.93	2.95	3.661 (2)	135
C16—H16A⋯Cg1ii	0.93	2.90	3.624 (2)	136

Symmetry codes: (i) ; (ii) .