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

The title Schiff base compound, C(20)H(14)ClNO(2), adopts an E configuration about the azomethine bond. The phenol and chloro-benzene rings form dihedral angles of 84.71 (9) and 80.70 (8)°, respectively, with the phenyl ring and are twisted by 15.32 (8)° with respect to one another. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯N hydrogen bond, which forms an S(6) ring motif. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming columns parallel to the a axis.

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: Aslam et al. (2011 ▶); Zeb & Yousuf (2011 ▶); Cox et al. (2008 ▶); Vasco-Mendez et al. (1996 ▶).

Experimental

Crystal data

C20H14ClNO2

M = 335.77

Triclinic,

a = 7.3904 (9) Å

b = 10.7933 (14) Å

c = 10.8999 (14) Å

α = 73.120 (2)°

β = 87.919 (3)°

γ = 82.953 (3)°

V = 825.71 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 273 K

0.43 × 0.19 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.903, T max = 0.962

9338 measured reflections

3066 independent reflections

2481 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.109

S = 1.03

3066 reflections

221 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.20 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/S1600536811048690/rz2667sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048690/rz2667Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048690/rz2667Isup3.cml

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

C20H14ClNO2	Z = 2
Mr = 335.77	F(000) = 348
Triclinic, P1	Dx = 1.351 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3904 (9) Å	Cell parameters from 3265 reflections
b = 10.7933 (14) Å	θ = 2.0–25.5°
c = 10.8999 (14) Å	µ = 0.24 mm−1
α = 73.120 (2)°	T = 273 K
β = 87.919 (3)°	Block, yellow
γ = 82.953 (3)°	0.43 × 0.19 × 0.16 mm
V = 825.71 (18) Å3

Bruker SMART APEX CCD area-detector diffractometer	3066 independent reflections
Radiation source: fine-focus sealed tube	2481 reflections with I > 2σ(I)
graphite	Rint = 0.016
ω scan	θmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.903, Tmax = 0.962	k = −13→13
9338 measured reflections	l = −13→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0541P)2 + 0.1538P] where P = (Fo2 + 2Fc2)/3
3066 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.17 e Å−3
1 restraint	Δρmin = −0.20 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	0.31204 (8)	0.24660 (5)	0.46997 (5)	0.0854 (2)
O1	0.59969 (16)	−0.21801 (12)	0.84282 (15)	0.0757 (4)
O2	0.2754 (2)	−0.32066 (12)	1.15776 (14)	0.0788 (4)
H2A	0.279 (3)	−0.254 (2)	1.0879 (11)	0.103 (8)*
N1	0.26996 (17)	−0.08203 (12)	1.00695 (12)	0.0487 (3)
C1	0.2475 (2)	−0.26589 (17)	1.25483 (17)	0.0612 (4)
C2	0.2341 (3)	−0.3472 (2)	1.3787 (2)	0.0828 (6)
H2B	0.2496	−0.4372	1.3938	0.099*
C3	0.1979 (3)	−0.2949 (3)	1.4788 (2)	0.0882 (7)
H3A	0.1878	−0.3502	1.5613	0.106*
C4	0.1761 (3)	−0.1621 (3)	1.45934 (19)	0.0817 (6)
H4A	0.1495	−0.1278	1.5279	0.098*
C5	0.1939 (2)	−0.0807 (2)	1.33794 (17)	0.0657 (5)
H5A	0.1819	0.0089	1.3249	0.079*
C6	0.2299 (2)	−0.13059 (16)	1.23310 (15)	0.0519 (4)
C7	0.2450 (2)	−0.04203 (15)	1.10631 (15)	0.0490 (4)
H7A	0.2363	0.0470	1.0967	0.059*
C8	0.28094 (19)	0.00455 (14)	0.88212 (14)	0.0454 (3)
C9	0.2189 (2)	0.13726 (15)	0.84612 (16)	0.0541 (4)
H9A	0.1692	0.1759	0.9076	0.065*
C10	0.2302 (2)	0.21192 (15)	0.72062 (17)	0.0580 (4)
H10A	0.1894	0.3006	0.6976	0.070*
C11	0.3023 (2)	0.15451 (16)	0.62954 (16)	0.0557 (4)
C12	0.3654 (2)	0.02359 (16)	0.66243 (16)	0.0550 (4)
H12A	0.4144	−0.0142	0.6001	0.066*
C13	0.3554 (2)	−0.05126 (14)	0.78849 (15)	0.0463 (4)
C14	0.4369 (2)	−0.19231 (15)	0.82362 (15)	0.0487 (4)
C15	0.3180 (2)	−0.29461 (14)	0.83004 (14)	0.0449 (3)
C16	0.1298 (2)	−0.26661 (16)	0.81996 (15)	0.0529 (4)
H16A	0.0760	−0.1813	0.8075	0.063*
C17	0.0220 (2)	−0.36421 (18)	0.82830 (17)	0.0626 (5)
H17A	−0.1041	−0.3450	0.8220	0.075*
C18	0.1019 (3)	−0.49073 (17)	0.84612 (18)	0.0657 (5)
H18A	0.0294	−0.5568	0.8520	0.079*
C19	0.2881 (3)	−0.51924 (16)	0.85517 (19)	0.0672 (5)
H19A	0.3412	−0.6045	0.8667	0.081*
C20	0.3961 (2)	−0.42217 (15)	0.84726 (16)	0.0558 (4)
H20A	0.5221	−0.4421	0.8535	0.067*

	U11	U22	U33	U12	U13	U23
Cl1	0.1056 (4)	0.0725 (3)	0.0594 (3)	−0.0004 (3)	0.0066 (3)	0.0054 (2)
O1	0.0506 (7)	0.0541 (7)	0.1234 (12)	0.0019 (5)	−0.0083 (7)	−0.0295 (7)
O2	0.1159 (12)	0.0473 (7)	0.0672 (9)	−0.0021 (7)	0.0064 (8)	−0.0111 (7)
N1	0.0531 (7)	0.0435 (7)	0.0492 (8)	−0.0035 (6)	0.0016 (6)	−0.0137 (6)
C1	0.0636 (11)	0.0598 (10)	0.0556 (10)	−0.0029 (8)	−0.0010 (8)	−0.0113 (8)
C2	0.0990 (16)	0.0672 (12)	0.0684 (13)	−0.0047 (11)	−0.0030 (11)	0.0004 (10)
C3	0.0985 (16)	0.1036 (18)	0.0499 (11)	−0.0121 (13)	−0.0008 (10)	−0.0024 (11)
C4	0.0866 (14)	0.1068 (18)	0.0524 (11)	−0.0116 (12)	0.0000 (10)	−0.0237 (11)
C5	0.0666 (11)	0.0776 (12)	0.0561 (11)	−0.0078 (9)	−0.0022 (8)	−0.0241 (9)
C6	0.0455 (8)	0.0593 (10)	0.0506 (9)	−0.0053 (7)	−0.0025 (7)	−0.0152 (7)
C7	0.0470 (8)	0.0467 (8)	0.0546 (9)	−0.0046 (6)	−0.0012 (7)	−0.0171 (7)
C8	0.0447 (8)	0.0415 (8)	0.0506 (9)	−0.0056 (6)	0.0003 (6)	−0.0139 (7)
C9	0.0634 (10)	0.0412 (8)	0.0596 (10)	−0.0012 (7)	0.0017 (8)	−0.0196 (7)
C10	0.0666 (10)	0.0385 (8)	0.0650 (11)	−0.0022 (7)	−0.0036 (8)	−0.0103 (8)
C11	0.0580 (10)	0.0499 (9)	0.0536 (9)	−0.0073 (7)	0.0001 (7)	−0.0058 (7)
C12	0.0596 (10)	0.0524 (9)	0.0520 (9)	−0.0025 (7)	0.0058 (7)	−0.0160 (7)
C13	0.0451 (8)	0.0407 (8)	0.0533 (9)	−0.0054 (6)	0.0017 (6)	−0.0143 (7)
C14	0.0503 (9)	0.0450 (8)	0.0507 (9)	−0.0005 (7)	0.0033 (7)	−0.0159 (7)
C15	0.0519 (8)	0.0416 (8)	0.0401 (8)	−0.0008 (6)	0.0008 (6)	−0.0122 (6)
C16	0.0542 (9)	0.0477 (9)	0.0551 (9)	0.0013 (7)	0.0013 (7)	−0.0153 (7)
C17	0.0517 (9)	0.0691 (11)	0.0684 (11)	−0.0096 (8)	0.0044 (8)	−0.0217 (9)
C18	0.0742 (12)	0.0551 (10)	0.0701 (12)	−0.0202 (9)	0.0031 (9)	−0.0167 (9)
C19	0.0777 (13)	0.0423 (9)	0.0805 (13)	−0.0027 (8)	−0.0081 (10)	−0.0169 (8)
C20	0.0565 (9)	0.0457 (9)	0.0640 (10)	0.0024 (7)	−0.0046 (8)	−0.0167 (8)

Cl1—C11	1.7386 (17)	C9—C10	1.377 (2)
O1—C14	1.2125 (18)	C9—H9A	0.9300
O2—C1	1.352 (2)	C10—C11	1.375 (2)
O2—H2A	0.882 (19)	C10—H10A	0.9300
N1—C7	1.277 (2)	C11—C12	1.378 (2)
N1—C8	1.4154 (19)	C12—C13	1.382 (2)
C1—C2	1.388 (3)	C12—H12A	0.9300
C1—C6	1.400 (2)	C13—C14	1.510 (2)
C2—C3	1.371 (3)	C14—C15	1.479 (2)
C2—H2B	0.9300	C15—C16	1.388 (2)
C3—C4	1.377 (3)	C15—C20	1.388 (2)
C3—H3A	0.9300	C16—C17	1.377 (2)
C4—C5	1.371 (3)	C16—H16A	0.9300
C4—H4A	0.9300	C17—C18	1.381 (3)
C5—C6	1.402 (2)	C17—H17A	0.9300
C5—H5A	0.9300	C18—C19	1.373 (3)
C6—C7	1.444 (2)	C18—H18A	0.9300
C7—H7A	0.9300	C19—C20	1.375 (2)
C8—C9	1.393 (2)	C19—H19A	0.9300
C8—C13	1.393 (2)	C20—H20A	0.9300
C1—O2—H2A	105.0 (12)	C9—C10—H10A	120.2
C7—N1—C8	122.32 (13)	C10—C11—C12	120.90 (15)
O2—C1—C2	118.41 (17)	C10—C11—Cl1	120.10 (13)
O2—C1—C6	121.81 (15)	C12—C11—Cl1	119.00 (14)
C2—C1—C6	119.78 (18)	C11—C12—C13	119.61 (15)
C3—C2—C1	120.0 (2)	C11—C12—H12A	120.2
C3—C2—H2B	120.0	C13—C12—H12A	120.2
C1—C2—H2B	120.0	C12—C13—C8	120.47 (14)
C2—C3—C4	121.19 (19)	C12—C13—C14	118.56 (14)
C2—C3—H3A	119.4	C8—C13—C14	120.87 (13)
C4—C3—H3A	119.4	O1—C14—C15	121.85 (14)
C5—C4—C3	119.4 (2)	O1—C14—C13	118.73 (14)
C5—C4—H4A	120.3	C15—C14—C13	119.39 (13)
C3—C4—H4A	120.3	C16—C15—C20	119.02 (14)
C4—C5—C6	121.1 (2)	C16—C15—C14	121.71 (13)
C4—C5—H5A	119.5	C20—C15—C14	119.26 (14)
C6—C5—H5A	119.5	C17—C16—C15	120.48 (15)
C1—C6—C5	118.54 (16)	C17—C16—H16A	119.8
C1—C6—C7	121.87 (15)	C15—C16—H16A	119.8
C5—C6—C7	119.59 (16)	C16—C17—C18	119.74 (16)
N1—C7—C6	122.09 (15)	C16—C17—H17A	120.1
N1—C7—H7A	119.0	C18—C17—H17A	120.1
C6—C7—H7A	119.0	C19—C18—C17	120.21 (16)
C9—C8—C13	118.64 (14)	C19—C18—H18A	119.9
C9—C8—N1	125.53 (14)	C17—C18—H18A	119.9
C13—C8—N1	115.80 (13)	C18—C19—C20	120.23 (16)
C10—C9—C8	120.82 (15)	C18—C19—H19A	119.9
C10—C9—H9A	119.6	C20—C19—H19A	119.9
C8—C9—H9A	119.6	C19—C20—C15	120.31 (16)
C11—C10—C9	119.56 (15)	C19—C20—H20A	119.8
C11—C10—H10A	120.2	C15—C20—H20A	119.8
O2—C1—C2—C3	−177.1 (2)	C11—C12—C13—C8	0.4 (2)
C6—C1—C2—C3	2.1 (3)	C11—C12—C13—C14	−175.92 (15)
C1—C2—C3—C4	−0.7 (4)	C9—C8—C13—C12	−0.7 (2)
C2—C3—C4—C5	−1.1 (4)	N1—C8—C13—C12	177.30 (13)
C3—C4—C5—C6	1.4 (3)	C9—C8—C13—C14	175.60 (14)
O2—C1—C6—C5	177.45 (16)	N1—C8—C13—C14	−6.4 (2)
C2—C1—C6—C5	−1.7 (3)	C12—C13—C14—O1	82.0 (2)
O2—C1—C6—C7	−1.6 (3)	C8—C13—C14—O1	−94.33 (19)
C2—C1—C6—C7	179.24 (16)	C12—C13—C14—C15	−96.24 (17)
C4—C5—C6—C1	0.0 (3)	C8—C13—C14—C15	87.42 (18)
C4—C5—C6—C7	179.05 (16)	O1—C14—C15—C16	173.85 (16)
C8—N1—C7—C6	178.60 (13)	C13—C14—C15—C16	−8.0 (2)
C1—C6—C7—N1	2.1 (2)	O1—C14—C15—C20	−5.8 (2)
C5—C6—C7—N1	−176.98 (15)	C13—C14—C15—C20	172.40 (14)
C7—N1—C8—C9	−18.6 (2)	C20—C15—C16—C17	0.7 (2)
C7—N1—C8—C13	163.59 (14)	C14—C15—C16—C17	−178.96 (15)
C13—C8—C9—C10	0.2 (2)	C15—C16—C17—C18	−0.4 (3)
N1—C8—C9—C10	−177.59 (15)	C16—C17—C18—C19	−0.2 (3)
C8—C9—C10—C11	0.6 (3)	C17—C18—C19—C20	0.4 (3)
C9—C10—C11—C12	−0.8 (3)	C18—C19—C20—C15	0.0 (3)
C9—C10—C11—Cl1	178.32 (13)	C16—C15—C20—C19	−0.5 (2)
C10—C11—C12—C13	0.3 (3)	C14—C15—C20—C19	179.16 (16)
Cl1—C11—C12—C13	−178.83 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1	0.89 (2)	1.80 (2)	2.6188 (19)	152.(2)
C7—H7A···O1i	0.93	2.57	3.353 (2)	142.
C17—H17A···O1ii	0.93	2.48	3.340 (2)	155.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N1	0.89 (2)	1.80 (2)	2.6188 (19)	152 (2)
C7—H7A⋯O1i	0.93	2.57	3.353 (2)	142
C17—H17A⋯O1ii	0.93	2.48	3.340 (2)	155

Symmetry codes: (i) ; (ii) .