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

The mol-ecule of the title Schiff base compound, C(20)H(13)ClN(2)O(3), assumes an E configuration about the C=N bond. The aromatic rings of the nitro-benzene and chloro-benzene groups are twisted by 13.89 (13)° and form dihedral angles of 76.38 (13) and 84.64 (13)°, respectively, with the phenyl ring. In the crystal, mol-ecules are linked into chains parallel to the b axis by C-H⋯π inter-actions.

Related literature

For the biological activity of Schiff bases, see: Khan et al. (2009 ▶); Gerdemann et al. (2002 ▶); Samadhiya & Halve (2001 ▶); Mallikarjun & Sangamesh (1997 ▶); Fioravanti et al. (1995 ▶); Solomon & Lowery (1993 ▶). For related structures, see: Zeb & Yousuf (2011 ▶); Cox et al. (2008 ▶); Vasco-Mendez et al. (1996 ▶).

Experimental

Crystal data

C20H13ClN2O3

M = 364.77

Monoclinic,

a = 7.231 (2) Å

b = 20.235 (6) Å

c = 11.942 (4) Å

β = 98.030 (6)°

V = 1730.1 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 273 K

0.22 × 0.13 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.948, T max = 0.974

9867 measured reflections

3117 independent reflections

2059 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.125

S = 1.06

3117 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.22 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/S1600536811046162/rz2660sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046162/rz2660Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046162/rz2660Isup3.cml

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

C20H13ClN2O3	F(000) = 752
Mr = 364.77	Dx = 1.400 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1927 reflections
a = 7.231 (2) Å	θ = 2.7–22.4°
b = 20.235 (6) Å	µ = 0.24 mm−1
c = 11.942 (4) Å	T = 273 K
β = 98.030 (6)°	Block, yellow
V = 1730.1 (9) Å3	0.22 × 0.13 × 0.11 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	3117 independent reflections
Radiation source: fine-focus sealed tube	2059 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω scan	θmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.948, Tmax = 0.974	k = −24→24
9867 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0442P)2 + 0.6878P] where P = (Fo2 + 2Fc2)/3
3117 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.22 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	0.19880 (13)	0.14369 (6)	0.09091 (6)	0.0991 (4)
O1	0.5383 (3)	0.18026 (11)	0.52750 (17)	0.0748 (6)
O2	0.2903 (3)	−0.18427 (11)	1.03849 (16)	0.0729 (6)
O3	0.3022 (4)	−0.08484 (12)	1.09952 (18)	0.1055 (9)
N1	0.2719 (3)	0.02909 (11)	0.54984 (17)	0.0546 (6)
N2	0.2951 (3)	−0.12485 (13)	1.02346 (19)	0.0610 (6)
C1	0.0800 (4)	0.16884 (13)	0.6054 (2)	0.0559 (7)
H1B	0.0152	0.1594	0.5344	0.067*
C2	−0.0173 (4)	0.18077 (15)	0.6959 (3)	0.0705 (9)
H2A	−0.1472	0.1797	0.6854	0.085*
C3	0.0798 (5)	0.19418 (15)	0.8012 (3)	0.0682 (9)
H3A	0.0151	0.2016	0.8620	0.082*
C4	0.2711 (5)	0.19659 (15)	0.8168 (2)	0.0631 (8)
H4A	0.3357	0.2058	0.8879	0.076*
C5	0.3672 (4)	0.18538 (13)	0.7273 (2)	0.0535 (7)
H5A	0.4970	0.1875	0.7382	0.064*
C6	0.2730 (4)	0.17095 (11)	0.6210 (2)	0.0442 (6)
C7	0.3806 (4)	0.15890 (12)	0.5257 (2)	0.0472 (6)
C8	0.2958 (3)	0.11941 (13)	0.42535 (19)	0.0444 (6)
C9	0.2807 (4)	0.14706 (15)	0.3181 (2)	0.0563 (7)
H9A	0.3118	0.1912	0.3093	0.068*
C10	0.2197 (4)	0.10903 (17)	0.2252 (2)	0.0590 (8)
C11	0.1768 (4)	0.04369 (17)	0.2359 (2)	0.0614 (8)
H11A	0.1375	0.0184	0.1719	0.074*
C12	0.1918 (4)	0.01582 (14)	0.3409 (2)	0.0610 (8)
H12A	0.1618	−0.0285	0.3480	0.073*
C13	0.2515 (4)	0.05276 (13)	0.43751 (19)	0.0462 (6)
C14	0.2730 (4)	−0.03103 (13)	0.5735 (2)	0.0488 (7)
H14A	0.2657	−0.0619	0.5154	0.059*
C15	0.2857 (3)	−0.05421 (12)	0.6908 (2)	0.0448 (6)
C16	0.3020 (4)	−0.01050 (14)	0.7803 (2)	0.0566 (7)
H16A	0.3102	0.0346	0.7667	0.068*
C17	0.3062 (4)	−0.03285 (14)	0.8895 (2)	0.0581 (8)
H17A	0.3180	−0.0034	0.9498	0.070*
C18	0.2927 (4)	−0.09993 (13)	0.9074 (2)	0.0478 (6)
C19	0.2786 (4)	−0.14440 (13)	0.8209 (2)	0.0531 (7)
H19A	0.2719	−0.1895	0.8351	0.064*
C20	0.2745 (4)	−0.12143 (13)	0.7120 (2)	0.0528 (7)
H20A	0.2642	−0.1512	0.6522	0.063*

	U11	U22	U33	U12	U13	U23
Cl1	0.0832 (7)	0.1653 (10)	0.0474 (4)	−0.0118 (6)	0.0041 (4)	0.0365 (5)
O1	0.0597 (14)	0.0966 (17)	0.0717 (14)	−0.0256 (12)	0.0214 (11)	−0.0183 (11)
O2	0.0972 (18)	0.0613 (14)	0.0608 (13)	−0.0026 (13)	0.0128 (11)	0.0164 (10)
O3	0.186 (3)	0.0809 (17)	0.0499 (13)	0.0053 (18)	0.0163 (15)	−0.0056 (12)
N1	0.0755 (18)	0.0418 (13)	0.0458 (12)	0.0014 (12)	0.0063 (11)	0.0035 (9)
N2	0.0676 (17)	0.0663 (17)	0.0484 (14)	0.0002 (14)	0.0057 (12)	0.0003 (12)
C1	0.0523 (19)	0.0556 (18)	0.0602 (17)	−0.0004 (14)	0.0091 (14)	−0.0060 (13)
C2	0.059 (2)	0.072 (2)	0.085 (2)	0.0021 (16)	0.0268 (18)	−0.0072 (17)
C3	0.089 (3)	0.063 (2)	0.0586 (19)	0.0127 (18)	0.0333 (18)	0.0035 (14)
C4	0.075 (2)	0.069 (2)	0.0452 (16)	0.0092 (17)	0.0094 (15)	0.0049 (13)
C5	0.0576 (18)	0.0553 (17)	0.0476 (15)	0.0049 (14)	0.0077 (13)	0.0037 (12)
C6	0.0493 (17)	0.0368 (14)	0.0471 (14)	−0.0004 (12)	0.0083 (12)	0.0031 (11)
C7	0.0489 (17)	0.0454 (16)	0.0477 (15)	−0.0028 (13)	0.0080 (12)	0.0039 (11)
C8	0.0408 (15)	0.0512 (16)	0.0424 (14)	0.0023 (12)	0.0108 (11)	0.0033 (11)
C9	0.0538 (18)	0.0645 (19)	0.0509 (17)	−0.0034 (15)	0.0085 (13)	0.0164 (14)
C10	0.0458 (18)	0.091 (2)	0.0409 (15)	0.0045 (16)	0.0086 (13)	0.0125 (15)
C11	0.0555 (19)	0.085 (2)	0.0417 (15)	0.0083 (17)	0.0012 (13)	−0.0088 (14)
C12	0.075 (2)	0.0539 (18)	0.0529 (17)	0.0018 (15)	0.0046 (15)	−0.0083 (13)
C13	0.0501 (17)	0.0494 (16)	0.0397 (13)	0.0052 (13)	0.0081 (12)	0.0005 (11)
C14	0.0530 (18)	0.0473 (17)	0.0476 (15)	0.0010 (13)	0.0122 (12)	−0.0015 (12)
C15	0.0436 (16)	0.0422 (15)	0.0494 (15)	0.0013 (12)	0.0098 (12)	0.0021 (11)
C16	0.071 (2)	0.0431 (16)	0.0543 (17)	−0.0057 (14)	0.0019 (14)	0.0019 (12)
C17	0.072 (2)	0.0481 (17)	0.0514 (16)	−0.0011 (15)	0.0002 (14)	−0.0074 (13)
C18	0.0462 (16)	0.0528 (17)	0.0433 (14)	0.0020 (13)	0.0027 (12)	0.0047 (12)
C19	0.0625 (19)	0.0424 (16)	0.0556 (16)	−0.0003 (13)	0.0130 (14)	0.0037 (12)
C20	0.0646 (19)	0.0447 (16)	0.0500 (15)	0.0019 (14)	0.0111 (13)	−0.0013 (12)

Cl1—C10	1.738 (3)	C8—C13	1.398 (3)
O1—C7	1.217 (3)	C9—C10	1.371 (4)
O2—N2	1.217 (3)	C9—H9A	0.9300
O3—N2	1.213 (3)	C10—C11	1.368 (4)
N1—C14	1.249 (3)	C11—C12	1.366 (4)
N1—C13	1.413 (3)	C11—H11A	0.9300
N2—C18	1.472 (3)	C12—C13	1.392 (4)
C1—C6	1.383 (4)	C12—H12A	0.9300
C1—C2	1.390 (4)	C14—C15	1.468 (3)
C1—H1B	0.9300	C14—H14A	0.9300
C2—C3	1.379 (4)	C15—C16	1.379 (4)
C2—H2A	0.9300	C15—C20	1.388 (3)
C3—C4	1.370 (4)	C16—C17	1.377 (4)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.372 (4)	C17—C18	1.380 (4)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C6	1.386 (3)	C18—C19	1.364 (4)
C5—H5A	0.9300	C19—C20	1.377 (3)
C6—C7	1.485 (3)	C19—H19A	0.9300
C7—C8	1.498 (3)	C20—H20A	0.9300
C8—C9	1.388 (3)
C14—N1—C13	122.8 (2)	C11—C10—Cl1	119.0 (2)
O3—N2—O2	123.3 (2)	C9—C10—Cl1	119.8 (3)
O3—N2—C18	118.0 (3)	C12—C11—C10	119.6 (3)
O2—N2—C18	118.7 (2)	C12—C11—H11A	120.2
C6—C1—C2	120.1 (3)	C10—C11—H11A	120.2
C6—C1—H1B	119.9	C11—C12—C13	121.0 (3)
C2—C1—H1B	119.9	C11—C12—H12A	119.5
C3—C2—C1	119.6 (3)	C13—C12—H12A	119.5
C3—C2—H2A	120.2	C12—C13—C8	118.7 (2)
C1—C2—H2A	120.2	C12—C13—N1	125.8 (2)
C4—C3—C2	120.5 (3)	C8—C13—N1	115.5 (2)
C4—C3—H3A	119.8	N1—C14—C15	121.7 (2)
C2—C3—H3A	119.8	N1—C14—H14A	119.2
C3—C4—C5	120.0 (3)	C15—C14—H14A	119.2
C3—C4—H4A	120.0	C16—C15—C20	119.2 (2)
C5—C4—H4A	120.0	C16—C15—C14	121.4 (2)
C4—C5—C6	120.7 (3)	C20—C15—C14	119.3 (2)
C4—C5—H5A	119.6	C17—C16—C15	120.7 (3)
C6—C5—H5A	119.6	C17—C16—H16A	119.6
C1—C6—C5	119.1 (2)	C15—C16—H16A	119.6
C1—C6—C7	121.3 (2)	C18—C17—C16	118.5 (2)
C5—C6—C7	119.6 (2)	C18—C17—H17A	120.7
O1—C7—C6	121.2 (2)	C16—C17—H17A	120.7
O1—C7—C8	118.8 (2)	C19—C18—C17	122.1 (2)
C6—C7—C8	120.0 (2)	C19—C18—N2	118.5 (2)
C9—C8—C13	119.7 (2)	C17—C18—N2	119.4 (2)
C9—C8—C7	119.6 (2)	C18—C19—C20	118.8 (3)
C13—C8—C7	120.4 (2)	C18—C19—H19A	120.6
C10—C9—C8	119.7 (3)	C20—C19—H19A	120.6
C10—C9—H9A	120.2	C19—C20—C15	120.6 (2)
C8—C9—H9A	120.2	C19—C20—H20A	119.7
C11—C10—C9	121.2 (3)	C15—C20—H20A	119.7
C6—C1—C2—C3	−0.5 (4)	C11—C12—C13—N1	179.9 (3)
C1—C2—C3—C4	0.8 (5)	C9—C8—C13—C12	−0.4 (4)
C2—C3—C4—C5	−0.2 (5)	C7—C8—C13—C12	−173.2 (2)
C3—C4—C5—C6	−0.6 (4)	C9—C8—C13—N1	179.7 (2)
C2—C1—C6—C5	−0.3 (4)	C7—C8—C13—N1	7.0 (3)
C2—C1—C6—C7	−179.5 (2)	C14—N1—C13—C12	14.4 (4)
C4—C5—C6—C1	0.9 (4)	C14—N1—C13—C8	−165.8 (3)
C4—C5—C6—C7	−179.9 (2)	C13—N1—C14—C15	−177.1 (2)
C1—C6—C7—O1	156.5 (3)	N1—C14—C15—C16	−1.8 (4)
C5—C6—C7—O1	−22.7 (4)	N1—C14—C15—C20	176.0 (3)
C1—C6—C7—C8	−24.0 (4)	C20—C15—C16—C17	−0.4 (4)
C5—C6—C7—C8	156.8 (2)	C14—C15—C16—C17	177.4 (2)
O1—C7—C8—C9	−57.3 (4)	C15—C16—C17—C18	−0.4 (4)
C6—C7—C8—C9	123.1 (3)	C16—C17—C18—C19	1.1 (4)
O1—C7—C8—C13	115.5 (3)	C16—C17—C18—N2	−179.4 (2)
C6—C7—C8—C13	−64.1 (3)	O3—N2—C18—C19	−177.9 (3)
C13—C8—C9—C10	1.0 (4)	O2—N2—C18—C19	2.2 (4)
C7—C8—C9—C10	173.8 (2)	O3—N2—C18—C17	2.6 (4)
C8—C9—C10—C11	−1.3 (4)	O2—N2—C18—C17	−177.2 (3)
C8—C9—C10—Cl1	179.5 (2)	C17—C18—C19—C20	−1.1 (4)
C9—C10—C11—C12	1.0 (4)	N2—C18—C19—C20	179.4 (2)
Cl1—C10—C11—C12	−179.7 (2)	C18—C19—C20—C15	0.4 (4)
C10—C11—C12—C13	−0.4 (5)	C16—C15—C20—C19	0.4 (4)
C11—C12—C13—C8	0.1 (4)	C14—C15—C20—C19	−177.5 (2)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···Cg1i	0.93	2.68	3.538 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19A⋯Cg1i	0.93	2.68	3.538 (3)	154

Symmetry code: (i) .