{5-Chloro-2-[(4-chloro-benzyl-idene)-amino]-phen-yl}(phen-yl)methanone.

In the title compound, C(20)H(13)Cl(2)NO, the C=N bond adopts an E conformation. The chloro-substituted rings form a dihedral angle of 11.99 (9)° with each other and form dihedral angles of 74.95 (9) and 83.26 (10)° with the unsubstituted ring. In the crystal, mol-ecules are connected into dimers by pairs of weak C-H⋯O hydrogen bonds and the dimers are arranged in columns parallel to the a axis.

Related literature

For the biological activities of Schiff base compounds, see: Solomon & Lowery (1993 ▶). For related structures, see: Aslam et al. (2011a ▶,b ▶); Zeb & Yousuf (2011 ▶).

Experimental

Crystal data

C20H13Cl2NO

M = 354.21

Triclinic,

a = 7.2283 (4) Å

b = 10.2301 (5) Å

c = 11.9079 (6) Å

α = 100.929 (1)°

β = 97.318 (1)°

γ = 91.360 (1)°

V = 856.49 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 273 K

0.39 × 0.14 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.865, T max = 0.963

9733 measured reflections

3186 independent reflections

2388 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.02

3186 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.23 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 datablock(s) global, I. DOI: 10.1107/S1600536812004655/lh5403sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004655/lh5403Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004655/lh5403Isup3.cml

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

C20H13Cl2NO	Z = 2
Mr = 354.21	F(000) = 364
Triclinic, P1	Dx = 1.373 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2283 (4) Å	Cell parameters from 2693 reflections
b = 10.2301 (5) Å	θ = 2.4–25.0°
c = 11.9079 (6) Å	µ = 0.38 mm−1
α = 100.929 (1)°	T = 273 K
β = 97.318 (1)°	Block, yellow
γ = 91.360 (1)°	0.39 × 0.14 × 0.10 mm
V = 856.49 (8) Å3

Bruker SMART APEX CCD diffractometer	3186 independent reflections
Radiation source: fine-focus sealed tube	2388 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.865, Tmax = 0.963	k = −12→12
9733 measured reflections	l = −14→14

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0503P)2 + 0.1325P] where P = (Fo2 + 2Fc2)/3
3186 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.23 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	0.21952 (9)	0.72197 (6)	0.48534 (5)	0.0772 (2)
Cl2	0.26120 (8)	0.21797 (7)	1.37525 (4)	0.0772 (2)
O1	−0.06787 (19)	0.12992 (15)	0.92259 (12)	0.0703 (4)
N1	0.2217 (2)	0.43376 (15)	0.94686 (13)	0.0534 (4)
C1	0.3968 (3)	0.1501 (2)	0.85494 (17)	0.0593 (5)
H1B	0.4588	0.1680	0.9300	0.071*
C2	0.4979 (3)	0.1263 (2)	0.7624 (2)	0.0747 (7)
H2A	0.6275	0.1257	0.7753	0.090*
C3	0.4060 (4)	0.1037 (2)	0.65140 (19)	0.0715 (6)
H3A	0.4740	0.0911	0.5893	0.086*
C4	0.2164 (3)	0.0997 (2)	0.63220 (17)	0.0640 (6)
H4A	0.1549	0.0833	0.5570	0.077*
C5	0.1152 (3)	0.12004 (19)	0.72373 (16)	0.0542 (5)
H5A	−0.0146	0.1154	0.7100	0.065*
C6	0.2049 (2)	0.14729 (16)	0.83616 (14)	0.0448 (4)
C7	0.0923 (3)	0.17452 (17)	0.93309 (15)	0.0465 (4)
C8	0.1764 (2)	0.25790 (17)	1.04654 (14)	0.0443 (4)
C9	0.1823 (2)	0.20517 (19)	1.14596 (15)	0.0507 (4)
H9A	0.1410	0.1174	1.1419	0.061*
C10	0.2499 (3)	0.2842 (2)	1.25056 (15)	0.0520 (5)
C11	0.3079 (3)	0.4151 (2)	1.25924 (16)	0.0566 (5)
H11A	0.3517	0.4674	1.3309	0.068*
C12	0.3006 (3)	0.4679 (2)	1.16108 (16)	0.0560 (5)
H12A	0.3397	0.5564	1.1668	0.067*
C13	0.2355 (2)	0.39071 (17)	1.05307 (14)	0.0453 (4)
C14	0.2384 (2)	0.55370 (18)	0.93892 (15)	0.0483 (4)
H14A	0.2559	0.6186	1.0061	0.058*
C15	0.2314 (2)	0.59480 (17)	0.82787 (15)	0.0448 (4)
C16	0.2588 (3)	0.72787 (18)	0.82228 (16)	0.0522 (5)
H16A	0.2787	0.7915	0.8902	0.063*
C17	0.2569 (3)	0.76737 (19)	0.71788 (17)	0.0550 (5)
H17A	0.2763	0.8568	0.7151	0.066*
C18	0.2260 (3)	0.6728 (2)	0.61789 (16)	0.0519 (5)
C19	0.1977 (3)	0.5396 (2)	0.62006 (17)	0.0595 (5)
H19A	0.1768	0.4766	0.5518	0.071*
C20	0.2007 (3)	0.50153 (19)	0.72493 (16)	0.0559 (5)
H20A	0.1819	0.4119	0.7272	0.067*

	U11	U22	U33	U12	U13	U23
Cl1	0.1037 (5)	0.0795 (4)	0.0541 (3)	−0.0031 (3)	0.0087 (3)	0.0294 (3)
Cl2	0.0884 (4)	0.1037 (5)	0.0477 (3)	0.0080 (3)	0.0099 (3)	0.0346 (3)
O1	0.0583 (9)	0.0847 (10)	0.0620 (9)	−0.0190 (8)	0.0089 (7)	0.0014 (7)
N1	0.0718 (11)	0.0451 (9)	0.0437 (9)	−0.0017 (7)	0.0051 (7)	0.0119 (7)
C1	0.0574 (12)	0.0635 (13)	0.0513 (11)	−0.0004 (10)	0.0015 (9)	0.0013 (9)
C2	0.0594 (13)	0.0807 (16)	0.0788 (16)	−0.0021 (11)	0.0199 (12)	−0.0038 (12)
C3	0.0960 (18)	0.0620 (13)	0.0584 (13)	−0.0072 (12)	0.0325 (12)	0.0032 (10)
C4	0.0888 (16)	0.0603 (13)	0.0429 (11)	−0.0038 (11)	0.0063 (10)	0.0130 (9)
C5	0.0624 (12)	0.0537 (11)	0.0463 (10)	0.0001 (9)	0.0008 (9)	0.0136 (8)
C6	0.0529 (10)	0.0389 (9)	0.0415 (9)	−0.0020 (8)	0.0026 (8)	0.0081 (7)
C7	0.0496 (10)	0.0441 (10)	0.0461 (10)	−0.0027 (8)	0.0024 (8)	0.0125 (8)
C8	0.0453 (9)	0.0475 (10)	0.0407 (9)	0.0010 (8)	0.0077 (7)	0.0091 (8)
C9	0.0518 (10)	0.0567 (11)	0.0474 (10)	−0.0009 (9)	0.0094 (8)	0.0181 (9)
C10	0.0489 (10)	0.0710 (13)	0.0404 (10)	0.0094 (9)	0.0077 (8)	0.0196 (9)
C11	0.0618 (12)	0.0670 (13)	0.0385 (10)	0.0059 (10)	0.0053 (8)	0.0044 (9)
C12	0.0702 (13)	0.0476 (11)	0.0475 (11)	−0.0010 (9)	0.0056 (9)	0.0044 (9)
C13	0.0490 (10)	0.0479 (10)	0.0398 (9)	0.0030 (8)	0.0074 (8)	0.0092 (8)
C14	0.0542 (11)	0.0454 (11)	0.0445 (10)	0.0002 (8)	0.0061 (8)	0.0072 (8)
C15	0.0428 (9)	0.0440 (10)	0.0482 (10)	0.0010 (7)	0.0063 (8)	0.0107 (8)
C16	0.0638 (12)	0.0421 (10)	0.0499 (11)	0.0017 (8)	0.0069 (9)	0.0076 (8)
C17	0.0655 (12)	0.0439 (10)	0.0581 (12)	0.0002 (9)	0.0082 (9)	0.0163 (9)
C18	0.0523 (10)	0.0586 (12)	0.0480 (11)	0.0010 (9)	0.0063 (8)	0.0190 (9)
C19	0.0775 (13)	0.0526 (12)	0.0459 (11)	−0.0047 (10)	0.0041 (9)	0.0069 (9)
C20	0.0710 (13)	0.0426 (10)	0.0539 (11)	−0.0041 (9)	0.0052 (9)	0.0119 (9)

Cl1—C18	1.7406 (18)	C9—C10	1.374 (3)
Cl2—C10	1.7389 (18)	C9—H9A	0.9300
O1—C7	1.217 (2)	C10—C11	1.375 (3)
N1—C14	1.253 (2)	C11—C12	1.373 (3)
N1—C13	1.409 (2)	C11—H11A	0.9300
C1—C6	1.375 (3)	C12—C13	1.394 (2)
C1—C2	1.385 (3)	C12—H12A	0.9300
C1—H1B	0.9300	C14—C15	1.457 (2)
C2—C3	1.377 (3)	C14—H14A	0.9300
C2—H2A	0.9300	C15—C16	1.386 (2)
C3—C4	1.359 (3)	C15—C20	1.393 (3)
C3—H3A	0.9300	C16—C17	1.377 (3)
C4—C5	1.375 (3)	C16—H16A	0.9300
C4—H4A	0.9300	C17—C18	1.374 (3)
C5—C6	1.385 (2)	C17—H17A	0.9300
C5—H5A	0.9300	C18—C19	1.379 (3)
C6—C7	1.483 (2)	C19—C20	1.375 (3)
C7—C8	1.501 (2)	C19—H19A	0.9300
C8—C9	1.387 (2)	C20—H20A	0.9300
C8—C13	1.399 (2)
C14—N1—C13	123.34 (16)	C12—C11—C10	119.37 (17)
C6—C1—C2	120.21 (19)	C12—C11—H11A	120.3
C6—C1—H1B	119.9	C10—C11—H11A	120.3
C2—C1—H1B	119.9	C11—C12—C13	120.96 (18)
C3—C2—C1	119.8 (2)	C11—C12—H12A	119.5
C3—C2—H2A	120.1	C13—C12—H12A	119.5
C1—C2—H2A	120.1	C12—C13—C8	118.58 (16)
C4—C3—C2	120.3 (2)	C12—C13—N1	126.03 (17)
C4—C3—H3A	119.9	C8—C13—N1	115.39 (15)
C2—C3—H3A	119.9	N1—C14—C15	122.11 (17)
C3—C4—C5	120.1 (2)	N1—C14—H14A	118.9
C3—C4—H4A	119.9	C15—C14—H14A	118.9
C5—C4—H4A	119.9	C16—C15—C20	118.33 (17)
C4—C5—C6	120.57 (19)	C16—C15—C14	120.65 (16)
C4—C5—H5A	119.7	C20—C15—C14	121.01 (16)
C6—C5—H5A	119.7	C17—C16—C15	121.11 (17)
C1—C6—C5	118.97 (17)	C17—C16—H16A	119.4
C1—C6—C7	121.64 (16)	C15—C16—H16A	119.4
C5—C6—C7	119.38 (16)	C18—C17—C16	119.08 (17)
O1—C7—C6	121.13 (16)	C18—C17—H17A	120.5
O1—C7—C8	119.03 (16)	C16—C17—H17A	120.5
C6—C7—C8	119.84 (15)	C17—C18—C19	121.44 (17)
C9—C8—C13	120.33 (16)	C17—C18—Cl1	119.46 (15)
C9—C8—C7	119.33 (16)	C19—C18—Cl1	119.10 (15)
C13—C8—C7	120.17 (15)	C20—C19—C18	118.84 (18)
C10—C9—C8	119.20 (17)	C20—C19—H19A	120.6
C10—C9—H9A	120.4	C18—C19—H19A	120.6
C8—C9—H9A	120.4	C19—C20—C15	121.20 (17)
C9—C10—C11	121.53 (17)	C19—C20—H20A	119.4
C9—C10—Cl2	119.45 (16)	C15—C20—H20A	119.4
C11—C10—Cl2	119.01 (15)
C6—C1—C2—C3	1.9 (3)	C10—C11—C12—C13	0.0 (3)
C1—C2—C3—C4	−2.4 (4)	C11—C12—C13—C8	0.3 (3)
C2—C3—C4—C5	0.8 (3)	C11—C12—C13—N1	180.00 (17)
C3—C4—C5—C6	1.3 (3)	C9—C8—C13—C12	0.3 (3)
C2—C1—C6—C5	0.2 (3)	C7—C8—C13—C12	175.50 (16)
C2—C1—C6—C7	−178.95 (19)	C9—C8—C13—N1	−179.44 (15)
C4—C5—C6—C1	−1.8 (3)	C7—C8—C13—N1	−4.2 (2)
C4—C5—C6—C7	177.37 (17)	C14—N1—C13—C12	−12.0 (3)
C1—C6—C7—O1	−154.66 (19)	C14—N1—C13—C8	167.63 (18)
C5—C6—C7—O1	26.2 (3)	C13—N1—C14—C15	177.31 (15)
C1—C6—C7—C8	25.1 (3)	N1—C14—C15—C16	−177.10 (18)
C5—C6—C7—C8	−154.06 (16)	N1—C14—C15—C20	1.7 (3)
O1—C7—C8—C9	57.0 (2)	C20—C15—C16—C17	−0.4 (3)
C6—C7—C8—C9	−122.72 (18)	C14—C15—C16—C17	178.42 (16)
O1—C7—C8—C13	−118.3 (2)	C15—C16—C17—C18	0.5 (3)
C6—C7—C8—C13	62.0 (2)	C16—C17—C18—C19	−0.3 (3)
C13—C8—C9—C10	−1.1 (3)	C16—C17—C18—Cl1	178.94 (14)
C7—C8—C9—C10	−176.41 (16)	C17—C18—C19—C20	0.0 (3)
C8—C9—C10—C11	1.4 (3)	Cl1—C18—C19—C20	−179.23 (15)
C8—C9—C10—Cl2	−178.96 (13)	C18—C19—C20—C15	0.1 (3)
C9—C10—C11—C12	−0.9 (3)	C16—C15—C20—C19	0.1 (3)
Cl2—C10—C11—C12	179.54 (14)	C14—C15—C20—C19	−178.70 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1i	0.93	2.52	3.426 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1i	0.93	2.52	3.426 (2)	164

Symmetry code: (i) .