[(4-Chloro­phen­yl)imino­meth­yl]phenol

In the mol­ecular structure of the title Schiff base, C₁₃H₁₀ClNO, the dihedral angle between the mean planes through the two benzene rings is 48.98 (8)°. The crystal structure is stabilized by inter­molecular O—H...N hydrogen bonds, which lead to the formation of one-dimensional zigzag chains running parallel to the c axis.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.036
• wR factor = 0.099
• Data-to-parameter ratio = 11.1

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S1. Comment

Schiff bases have attracted much attention not only due to their versatile coordination chemistry but also due to their antibacterial, anticancer, anti-inflammatory and antitoxic properties (Williams, 1972). Further, the thermochromism, photochromism and non-linear optical properties of this class of compounds has found numerous applications in modern technologies (Sekikawa et al., 1997). As a part of our reseach in assessing the second harmonic generation (SHG) efficiency of Schiff base compounds, we have undertaken the crystallographic analysis of the title compound, (I).

Compound (I) exists in the solid state in a non-planar conformation arising mainly from the rotation of the benzylidene moiety about the N1—C8 bond with a C7—N1—C8—C13 torsion angle of -34.8 (2)°. The dihedral angle between the planes of the chlorophenyl and hydroxyphenyl rings is 48.98 (8)°. The N1═ C7 bond distance of 1.283 (2) Å is characteristic of a double bond [1.282 (2) A°; Kazak et al., 2000]. The Cl1—C11 bond distance of 1.7375 (19) Å and the O1—C1 bond distance of 1.349 (2) Å are similar to the corresponding distances in 4-[(4-chlorobenzylidene)amino]phenol [1.741 (2) Å; Kazak et al., 2004] and N-(p-hydroxybenzylidene)phenylamine N–oxide [1.353 (3) Å; Vijayalakshmi et al., 1997], respectively. Other selected bond distances and angles are listed in Table 1.

The crystal structure of (I) is stabilized by intermolecular O—H···N hydrogen bonds formed between the phenol group and the imine nitrogen atom. This interaction leads to the formation of one-dimensional zigzag chains, which propagate along the c axis (Fig. 2 and Table 2).

Related literature

For related literature, see: Kazak et al., (2000, 2004); Sekikawa et al. (1997); Vijayalakshmi et al. (1997); Williams (1972).

S2. Experimental

The title compound, (I), was prepared by the reaction of 4-hydroxybenzaldehyde with 4-chloroaniline (molar ratio 1:1) in absolute ethanol. The reaction mixture was heated under refluxed for 4 h. The resulting solution was filtered and the filtrated allowed to stand in air for about 2 days giving a yellow solid. Good quality crystals were obtained by recrystallized from methanol.

S3. Refinement

The H-atoms were located from difference Fourier maps and freely refined: C—H = 0.934 (19) - 1.001 (19) Å.

Computing details

Data collection: X-AREA (Stoe & Cie, 2006); cell refinement: X-AREA (Stoe & Cie, 2006); data reduction: X-RED32 (Stoe & Cie, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

	Fig. 1. View of the molecular structure of compound (I), showing the atom labelling scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. View, along the a axis, of the crystal packing in compound (I). The intermolecular O—H···N hydrogen bonds are shown as dashed lines [symmetry operator (i) = -x + 1/2, -y + 1/2, z - 1/2].

[(4-Chlorophenyl)iminomethyl]phenol

Crystal data

C13H10ClNO	F(000) = 960
Mr = 231.67	Dx = 1.406 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 11010 reflections
a = 21.3211 (18) Å	θ = 1.9–26.1°
b = 11.0697 (10) Å	µ = 0.32 mm^−1
c = 9.2754 (10) Å	T = 173 K
V = 2189.2 (4) Å^3	Plate, pale-yellow
Z = 8	0.45 × 0.40 × 0.20 mm

Data collection

Stoe IPDS2 diffractometer	1662 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
Graphite monochromator	θmax = 25.7°, θmin = 1.9°
Detector resolution: 6.67 pixels mm^-1	h = −25→23
ϕ & ω scans	k = −13→13
14167 measured reflections	l = −11→11
2070 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	All H-atom parameters refined
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0603P)^2 + 0.2783P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2070 reflections	Δρmax = 0.38 e Å^−3
186 parameters	Δρmin = −0.49 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0094 (17)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.48652 (3)	0.83860 (5)	1.00582 (6)	0.0538 (2)
O1	0.12979 (6)	0.25164 (11)	0.25210 (13)	0.0345 (4)
N1	0.33136 (7)	0.47845 (12)	0.69545 (14)	0.0274 (4)
C1	0.16661 (8)	0.30820 (14)	0.34915 (17)	0.0272 (5)
C2	0.22508 (8)	0.26384 (15)	0.39185 (17)	0.0273 (5)
C3	0.26144 (8)	0.32800 (15)	0.48853 (17)	0.0274 (5)
C4	0.24065 (8)	0.43796 (15)	0.54534 (17)	0.0271 (5)
C5	0.18169 (8)	0.48131 (15)	0.50178 (18)	0.0304 (5)
C6	0.14498 (8)	0.41745 (15)	0.40608 (19)	0.0303 (5)
C7	0.27980 (8)	0.51329 (15)	0.63758 (17)	0.0282 (5)
C8	0.36938 (8)	0.56623 (15)	0.76578 (17)	0.0275 (5)
C9	0.40427 (8)	0.53086 (16)	0.88569 (18)	0.0323 (5)
C10	0.44020 (9)	0.61442 (18)	0.9602 (2)	0.0363 (6)
C11	0.44232 (8)	0.73248 (17)	0.9124 (2)	0.0362 (6)
C12	0.41060 (9)	0.76778 (17)	0.7893 (2)	0.0363 (5)
C13	0.37430 (8)	0.68476 (16)	0.71684 (19)	0.0325 (5)
H1O	0.1452 (13)	0.171 (3)	0.229 (3)	0.078 (8)*
H2	0.2404 (9)	0.188 (2)	0.352 (2)	0.036 (5)*
H3	0.3029 (9)	0.2982 (17)	0.5113 (19)	0.032 (5)*
H5	0.1673 (9)	0.5574 (18)	0.538 (2)	0.032 (5)*
H6	0.1032 (9)	0.4479 (18)	0.373 (2)	0.037 (5)*
H7	0.2644 (9)	0.5966 (19)	0.648 (2)	0.034 (5)*
H9	0.4030 (9)	0.4458 (18)	0.920 (2)	0.033 (5)*
H10	0.4615 (9)	0.5918 (18)	1.044 (2)	0.036 (5)*
H12	0.4148 (11)	0.852 (2)	0.757 (2)	0.057 (6)*
H13	0.3539 (10)	0.7085 (19)	0.629 (2)	0.042 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0487 (4)	0.0569 (4)	0.0558 (3)	−0.0189 (2)	−0.0028 (2)	−0.0194 (2)
O1	0.0378 (7)	0.0292 (7)	0.0365 (7)	−0.0010 (5)	−0.0084 (5)	−0.0047 (5)
N1	0.0336 (8)	0.0238 (7)	0.0248 (6)	−0.0035 (6)	0.0030 (6)	−0.0005 (5)
C1	0.0320 (9)	0.0239 (8)	0.0257 (8)	−0.0045 (7)	−0.0003 (7)	0.0024 (6)
C2	0.0330 (9)	0.0225 (8)	0.0265 (8)	0.0002 (7)	0.0025 (7)	−0.0008 (6)
C3	0.0297 (9)	0.0248 (8)	0.0277 (8)	0.0003 (7)	0.0026 (7)	0.0028 (6)
C4	0.0318 (9)	0.0235 (8)	0.0261 (8)	−0.0031 (7)	0.0027 (6)	0.0011 (6)
C5	0.0347 (9)	0.0224 (9)	0.0340 (9)	0.0003 (7)	0.0045 (7)	−0.0014 (7)
C6	0.0298 (9)	0.0259 (9)	0.0353 (9)	0.0011 (7)	−0.0003 (7)	0.0019 (7)
C7	0.0337 (9)	0.0232 (8)	0.0276 (8)	−0.0012 (7)	0.0044 (7)	−0.0011 (6)
C8	0.0304 (8)	0.0272 (9)	0.0250 (8)	−0.0008 (7)	0.0044 (7)	−0.0022 (6)
C9	0.0341 (9)	0.0309 (10)	0.0320 (9)	0.0017 (7)	0.0001 (7)	0.0006 (7)
C10	0.0325 (9)	0.0427 (10)	0.0338 (10)	0.0024 (8)	−0.0039 (8)	−0.0037 (8)
C11	0.0307 (9)	0.0396 (10)	0.0382 (10)	−0.0062 (8)	0.0032 (7)	−0.0106 (8)
C12	0.0411 (10)	0.0289 (9)	0.0388 (9)	−0.0069 (8)	0.0052 (8)	−0.0017 (7)
C13	0.0381 (9)	0.0293 (9)	0.0301 (9)	−0.0023 (7)	0.0000 (7)	0.0018 (7)

Geometric parameters (Å, º)

Cl1—C11	1.7375 (19)	C9—C10	1.386 (3)
O1—C1	1.349 (2)	C10—C11	1.381 (3)
O1—H1O	0.98 (3)	C11—C12	1.383 (3)
N1—C8	1.424 (2)	C12—C13	1.377 (3)
N1—C7	1.283 (2)	C2—H2	0.97 (2)
C1—C6	1.398 (2)	C3—H3	0.967 (19)
C1—C2	1.397 (2)	C5—H5	0.96 (2)
C2—C3	1.382 (2)	C6—H6	1.001 (19)
C3—C4	1.399 (2)	C7—H7	0.98 (2)
C4—C5	1.405 (2)	C9—H9	0.99 (2)
C4—C7	1.457 (2)	C10—H10	0.934 (19)
C5—C6	1.379 (2)	C12—H12	0.98 (2)
C8—C13	1.392 (2)	C13—H13	0.960 (19)
C8—C9	1.394 (2)
Cl1···C12^i	3.594 (2)	C9···H3^x	3.100 (19)
Cl1···Cl1^ii	3.6209 (9)	C9···H1O^v	2.87 (3)
Cl1···C6^iii	3.5839 (19)	C10···H10^xi	3.10 (2)
Cl1···H6^iii	2.986 (19)	C13···H7	2.617 (19)
O1···N1^iv	2.7294 (18)	H1O···H2	2.34 (3)
O1···H3^iv	2.712 (18)	H1O···N1^iv	1.76 (3)
O1···H9^iv	2.773 (19)	H1O···C3^iv	2.99 (3)
N1···O1^v	2.7294 (18)	H1O···C7^iv	2.73 (3)
N1···C10^vi	3.347 (2)	H1O···C8^iv	2.67 (3)
N1···C9^vi	3.268 (2)	H1O···C9^iv	2.87 (3)
N1···H3	2.696 (18)	H1O···H3^iv	2.33 (3)
N1···H2^v	2.80 (2)	H1O···H9^iv	2.42 (4)
N1···H1O^v	1.76 (3)	H2···H1O	2.34 (3)
C2···C7^vii	3.591 (2)	H2···N1^iv	2.80 (2)
C3···C9^vi	3.553 (2)	H2···C7^iv	3.02 (2)
C3···C13^vi	3.487 (2)	H3···N1	2.696 (18)
C3···C8^vi	3.307 (2)	H3···O1^v	2.712 (18)
C6···Cl1^viii	3.5839 (19)	H3···H1O^v	2.33 (3)
C7···C2^ix	3.591 (2)	H3···C8^vi	3.074 (18)
C7···C9^vi	3.569 (2)	H3···C9^vi	3.100 (19)
C8···C3^x	3.307 (2)	H5···H7	2.35 (3)
C9···N1^x	3.268 (2)	H6···H12^xii	2.49 (3)
C9···C3^x	3.553 (2)	H6···Cl1^viii	2.986 (19)
C9···C7^x	3.569 (2)	H7···C13	2.617 (19)
C10···N1^x	3.347 (2)	H7···H5	2.35 (3)
C12···Cl1^i	3.594 (2)	H7···H13	2.28 (3)
C13···C3^x	3.487 (2)	H7···C2^ix	3.02 (2)
C1···H13^vii	2.854 (19)	H7···C3^ix	3.01 (2)
C1···H7^vi	2.990 (19)	H7···C1^x	2.990 (19)
C2···H7^vi	2.865 (19)	H7···C2^x	2.865 (19)
C2···H7^vii	3.02 (2)	H9···O1^v	2.77 (2)
C2···H13^vii	2.84 (2)	H9···H1O^v	2.42 (3)
C3···H1O^v	2.99 (3)	H10···C10^xi	3.10 (2)
C3···H13^vii	3.08 (2)	H12···H6^xiii	2.49 (3)
C3···H7^vii	3.01 (2)	H13···C7	2.68 (2)
C7···H13	2.68 (2)	H13···H7	2.28 (3)
C7···H1O^v	2.73 (3)	H13···C1^ix	2.854 (19)
C7···H2^v	3.02 (2)	H13···C2^ix	2.84 (2)
C8···H1O^v	2.67 (3)	H13···C3^ix	3.08 (2)
C8···H3^x	3.074 (18)
C1—O1—H1O	112.1 (16)	C11—C12—C13	119.29 (17)
C7—N1—C8	118.33 (14)	C8—C13—C12	120.81 (16)
O1—C1—C6	117.50 (15)	C1—C2—H2	119.7 (11)
C2—C1—C6	119.43 (15)	C3—C2—H2	120.1 (11)
O1—C1—C2	123.06 (14)	C2—C3—H3	118.6 (11)
C1—C2—C3	120.26 (15)	C4—C3—H3	120.3 (11)
C2—C3—C4	120.93 (16)	C4—C5—H5	119.1 (12)
C3—C4—C5	118.20 (15)	C6—C5—H5	119.7 (11)
C5—C4—C7	119.07 (15)	C1—C6—H6	118.0 (11)
C3—C4—C7	122.52 (15)	C5—C6—H6	122.0 (11)
C4—C5—C6	121.20 (15)	N1—C7—H7	121.8 (11)
C1—C6—C5	119.97 (16)	C4—C7—H7	113.8 (11)
N1—C7—C4	124.37 (15)	C8—C9—H9	120.5 (11)
N1—C8—C13	122.46 (15)	C10—C9—H9	119.2 (11)
C9—C8—C13	118.98 (16)	C9—C10—H10	120.3 (12)
N1—C8—C9	118.53 (15)	C11—C10—H10	120.3 (12)
C8—C9—C10	120.36 (16)	C11—C12—H12	118.3 (12)
C9—C10—C11	119.33 (17)	C13—C12—H12	122.4 (12)
Cl1—C11—C10	119.84 (14)	C8—C13—H13	120.0 (13)
Cl1—C11—C12	119.07 (15)	C12—C13—H13	119.1 (13)
C10—C11—C12	121.09 (17)
C8—N1—C7—C4	171.05 (15)	C5—C4—C7—N1	172.70 (16)
C7—N1—C8—C9	147.05 (16)	C4—C5—C6—C1	−0.8 (3)
C7—N1—C8—C13	−34.8 (2)	N1—C8—C9—C10	−177.79 (16)
O1—C1—C2—C3	178.01 (15)	C13—C8—C9—C10	4.0 (3)
C6—C1—C2—C3	−0.6 (2)	N1—C8—C13—C12	178.74 (16)
O1—C1—C6—C5	−177.68 (15)	C9—C8—C13—C12	−3.1 (3)
C2—C1—C6—C5	1.0 (2)	C8—C9—C10—C11	−1.6 (3)
C1—C2—C3—C4	0.0 (2)	C9—C10—C11—Cl1	179.33 (14)
C2—C3—C4—C5	0.2 (2)	C9—C10—C11—C12	−1.8 (3)
C2—C3—C4—C7	−174.53 (15)	Cl1—C11—C12—C13	−178.45 (14)
C3—C4—C5—C6	0.2 (2)	C10—C11—C12—C13	2.7 (3)
C7—C4—C5—C6	175.13 (16)	C11—C12—C13—C8	−0.2 (3)
C3—C4—C7—N1	−12.6 (3)

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, −y+2, −z+2; (iii) x+1/2, y+1/2, −z+3/2; (iv) −x+1/2, −y+1/2, z−1/2; (v) −x+1/2, −y+1/2, z+1/2; (vi) x, −y+1, z−1/2; (vii) −x+1/2, y−1/2, z; (viii) x−1/2, y−1/2, −z+3/2; (ix) −x+1/2, y+1/2, z; (x) x, −y+1, z+1/2; (xi) −x+1, −y+1, −z+2; (xii) −x+1/2, −y+3/2, z−1/2; (xiii) −x+1/2, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1^iv	0.98 (3)	1.76 (3)	2.7294 (18)	176 (2)

Symmetry code: (iv) −x+1/2, −y+1/2, z−1/2.