2-[(E)-(5-Chloro-2-methyl-phen-yl)imino-meth-yl]-4-methyl-phenol.

In the mol-ecule of the title Schiff base compound, C15H14ClNO, the two benzene rings are twisted with respect to each other, with a dihedral angle of 35.0 (3)°; an intra-molecular O-H⋯N hydrogen bond occurs. In the crystal, weak C-H⋯π inter-actions between methyl groups and chloro-phenyl rings link the mol-ecules into supra-molecular chains running along the a axis.

Related literature

For background to phyenyl­amine compounds, see: Fan et al. (2012 ▶). For applications of Schiff base derivatives, see: Siddiqui et al. (2006 ▶); Ebrahimipour et al. (2012 ▶).

Experimental

Crystal data

C15H14ClNO

M = 259.72

Orthorhombic,

a = 7.6629 (10) Å

b = 11.8442 (14) Å

c = 14.342 (2) Å

V = 1301.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.45 × 0.42 × 0.35 mm

Data collection

Agilent Xcalibur Gemini ultra diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.88, T max = 0.91

8663 measured reflections

2382 independent reflections

1769 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.100

S = 1.03

2382 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), with 991 Friedel pairs

Absolute structure parameter: −0.18 (9)

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813019454/xu5720sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019454/xu5720Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019454/xu5720Isup3.cml

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

C15H14ClNO	F(000) = 544
Mr = 259.72	Dx = 1.325 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1894 reflections
a = 7.6629 (10) Å	θ = 3.4–29.6°
b = 11.8442 (14) Å	µ = 0.28 mm−1
c = 14.342 (2) Å	T = 293 K
V = 1301.7 (3) Å3	Block, yellow
Z = 4	0.45 × 0.42 × 0.35 mm

Agilent Xcalibur Gemini ultra diffractometer with Atlas detector	2382 independent reflections
Radiation source: fine-focus sealed tube	1769 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 10.3592 pixels mm-1	θmax = 25.4°, θmin = 3.4°
ω scans	h = −9→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −14→14
Tmin = 0.88, Tmax = 0.91	l = −15→17
8663 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.041	w = 1/[σ2(Fo2) + (0.0463P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.100	(Δ/σ)max = 0.002
S = 1.03	Δρmax = 0.16 e Å−3
2382 reflections	Δρmin = −0.17 e Å−3
169 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.024 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 991 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.18 (9)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.87007 (10)	0.98698 (7)	0.87968 (5)	0.0705 (3)
O1	1.1714 (3)	1.01909 (17)	0.36679 (14)	0.0651 (6)
N1	1.0171 (3)	0.99976 (18)	0.52972 (14)	0.0456 (5)
C1	1.1228 (3)	1.1295 (2)	0.36948 (19)	0.0449 (6)
C2	1.1680 (4)	1.1989 (2)	0.2958 (2)	0.0510 (7)
H2	1.2327	1.1705	0.2462	0.061*
C3	1.1167 (4)	1.3109 (2)	0.29627 (19)	0.0498 (7)
H3	1.1449	1.3561	0.2454	0.060*
C4	1.0248 (3)	1.3579 (2)	0.36974 (19)	0.0451 (7)
C5	0.9829 (3)	1.2883 (2)	0.44320 (19)	0.0421 (6)
H5	0.9215	1.3181	0.4934	0.050*
C6	1.0296 (3)	1.1738 (2)	0.44475 (18)	0.0395 (6)
C7	0.9729 (4)	1.4803 (2)	0.3692 (2)	0.0653 (8)
H7A	0.8860	1.4932	0.4162	0.098*
H7B	0.9261	1.4996	0.3092	0.098*
H7C	1.0733	1.5263	0.3818	0.098*
C8	0.9758 (3)	1.1045 (2)	0.52278 (19)	0.0458 (7)
H8	0.9087	1.1370	0.5697	0.055*
C9	0.9585 (3)	0.9368 (2)	0.6085 (2)	0.0446 (7)
C10	0.9508 (3)	0.9850 (2)	0.69650 (18)	0.0459 (6)
H10	0.9883	1.0589	0.7055	0.055*
C11	0.8874 (4)	0.9232 (2)	0.77061 (19)	0.0493 (7)
C12	0.8366 (4)	0.8127 (3)	0.7589 (2)	0.0596 (8)
H12	0.7943	0.7710	0.8089	0.071*
C13	0.8498 (4)	0.7652 (2)	0.6719 (2)	0.0593 (8)
H13	0.8168	0.6901	0.6644	0.071*
C14	0.9102 (3)	0.8243 (2)	0.5945 (2)	0.0503 (7)
C15	0.9174 (4)	0.7697 (2)	0.5002 (2)	0.0680 (9)
H15A	1.0351	0.7715	0.4773	0.102*
H15B	0.8427	0.8099	0.4579	0.102*
H15C	0.8791	0.6927	0.5050	0.102*
H1	1.136 (5)	0.993 (3)	0.418 (3)	0.102*

	U11	U22	U33	U12	U13	U23
Cl1	0.0837 (5)	0.0789 (6)	0.0487 (5)	0.0012 (4)	0.0059 (4)	0.0083 (4)
O1	0.0850 (14)	0.0494 (12)	0.0608 (14)	0.0107 (11)	0.0181 (11)	−0.0039 (11)
N1	0.0509 (12)	0.0429 (12)	0.0430 (13)	−0.0007 (12)	−0.0008 (10)	0.0014 (11)
C1	0.0489 (14)	0.0421 (14)	0.0439 (17)	−0.0003 (12)	0.0010 (14)	−0.0065 (13)
C2	0.0581 (17)	0.0534 (17)	0.0414 (16)	−0.0070 (14)	0.0103 (14)	−0.0092 (14)
C3	0.0590 (16)	0.0519 (16)	0.0386 (16)	−0.0127 (16)	0.0026 (14)	0.0014 (13)
C4	0.0463 (14)	0.0429 (14)	0.0460 (18)	−0.0033 (12)	−0.0052 (13)	0.0036 (13)
C5	0.0442 (14)	0.0442 (14)	0.0378 (16)	−0.0006 (12)	0.0034 (12)	−0.0058 (12)
C6	0.0409 (13)	0.0416 (14)	0.0360 (16)	−0.0039 (12)	−0.0008 (12)	−0.0009 (12)
C7	0.0764 (19)	0.0512 (16)	0.068 (2)	0.0039 (16)	0.0027 (17)	0.0091 (17)
C8	0.0445 (15)	0.0480 (15)	0.0447 (18)	−0.0003 (13)	0.0003 (13)	−0.0012 (13)
C9	0.0411 (14)	0.0421 (14)	0.0505 (19)	0.0006 (11)	−0.0003 (13)	0.0066 (13)
C10	0.0464 (14)	0.0417 (13)	0.0497 (17)	−0.0017 (13)	−0.0003 (12)	0.0056 (14)
C11	0.0475 (16)	0.0528 (16)	0.0475 (18)	0.0044 (14)	0.0002 (14)	0.0111 (13)
C12	0.0596 (19)	0.0546 (19)	0.064 (2)	−0.0002 (15)	0.0067 (15)	0.0199 (16)
C13	0.0618 (19)	0.0399 (15)	0.076 (2)	−0.0021 (14)	0.0013 (17)	0.0095 (16)
C14	0.0469 (16)	0.0437 (15)	0.060 (2)	0.0048 (13)	−0.0010 (14)	0.0052 (14)
C15	0.075 (2)	0.0530 (17)	0.076 (2)	−0.0040 (16)	0.0029 (17)	−0.0109 (17)

Cl1—C11	1.742 (3)	C7—H7B	0.9600
O1—C1	1.361 (3)	C7—H7C	0.9600
O1—H1	0.84 (4)	C8—H8	0.9300
N1—C8	1.284 (3)	C9—C10	1.387 (4)
N1—C9	1.426 (3)	C9—C14	1.397 (3)
C1—C2	1.383 (4)	C10—C11	1.379 (3)
C1—C6	1.396 (3)	C10—H10	0.9300
C2—C3	1.383 (4)	C11—C12	1.376 (4)
C2—H2	0.9300	C12—C13	1.372 (4)
C3—C4	1.384 (4)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.392 (4)
C4—C5	1.376 (3)	C13—H13	0.9300
C4—C7	1.503 (4)	C14—C15	1.501 (4)
C5—C6	1.403 (3)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—C8	1.448 (3)	C15—H15C	0.9600
C7—H7A	0.9600
C1—O1—H1	104 (3)	N1—C8—H8	118.8
C8—N1—C9	119.3 (2)	C6—C8—H8	118.8
O1—C1—C2	118.8 (2)	C10—C9—C14	120.8 (2)
O1—C1—C6	121.5 (2)	C10—C9—N1	121.2 (2)
C2—C1—C6	119.7 (2)	C14—C9—N1	117.9 (2)
C1—C2—C3	119.7 (3)	C11—C10—C9	119.8 (2)
C1—C2—H2	120.2	C11—C10—H10	120.1
C3—C2—H2	120.2	C9—C10—H10	120.1
C2—C3—C4	122.3 (2)	C12—C11—C10	120.7 (3)
C2—C3—H3	118.9	C12—C11—Cl1	120.1 (2)
C4—C3—H3	118.9	C10—C11—Cl1	119.3 (2)
C5—C4—C3	117.4 (2)	C13—C12—C11	118.7 (3)
C5—C4—C7	121.3 (2)	C13—C12—H12	120.6
C3—C4—C7	121.3 (2)	C11—C12—H12	120.6
C4—C5—C6	122.1 (2)	C12—C13—C14	122.9 (3)
C4—C5—H5	118.9	C12—C13—H13	118.6
C6—C5—H5	118.9	C14—C13—H13	118.6
C1—C6—C5	118.7 (2)	C13—C14—C9	117.0 (3)
C1—C6—C8	122.1 (2)	C13—C14—C15	121.0 (2)
C5—C6—C8	119.2 (2)	C9—C14—C15	122.0 (3)
C4—C7—H7A	109.5	C14—C15—H15A	109.5
C4—C7—H7B	109.5	C14—C15—H15B	109.5
H7A—C7—H7B	109.5	H15A—C15—H15B	109.5
C4—C7—H7C	109.5	C14—C15—H15C	109.5
H7A—C7—H7C	109.5	H15A—C15—H15C	109.5
H7B—C7—H7C	109.5	H15B—C15—H15C	109.5
N1—C8—C6	122.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84 (4)	1.84 (4)	2.629 (3)	154 (4)
C7—H7C···Cg1i	0.96	2.91	3.767 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84 (4)	1.84 (4)	2.629 (3)	154 (4)
C7—H7C⋯Cg1i	0.96	2.91	3.767 (3)	149

Symmetry code: (i) .