(E)-4-Chloro-2-{[4-(di-methyl-amino)-benzyl-idene]amino}-phenol.

In the title aromatic Schiff base compound, C15H15ClN2O, the mol-ecule exists in a trans conformation with respect to the C=N bond. The dihedral angle between the benzene rings is 14.49 (6)°. In the crystal, weak C-H⋯π inter-actions link mol-ecules into supra-molecular chains propagated along the a-axis direction.

Related literature

For the use of Schiff bases in synthesis, see: Arora et al. (2002 ▶). For their use as biological, analytical, polymer and liquid crystalline materials, see: Tanaka & Shiraishi (2000 ▶). Schiff bases have been reported to show anti­bacterial (Jarrahpour & Khalili, 2006 ▶; Jarrahpour et al., 2004 ▶; El-masry et al., 2000 ▶), anti­fungal (More et al., 2001 ▶; Singh & Dash, 1988 ▶), anti­cancer (Desai et al., 2001 ▶; Phatak et al., 2000 ▶) and herbicidal activity (Samadhiya & Halve, 2001 ▶). For related structures, see: Akkurt et al. (2005 ▶, 2008 ▶).

Experimental

Crystal data

C15H15ClN2O

M = 274.74

Orthorhombic,

a = 7.411 (5) Å

b = 12.314 (5) Å

c = 29.684 (5) Å

V = 2709 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.03 × 0.02 × 0.01 mm

Data collection

Bruker APEXII CCD diffractometer

14319 measured reflections

2346 independent reflections

1895 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.102

S = 1.10

2346 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814008873/xu5785sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008873/xu5785Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814008873/xu5785Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H15ClN2O	Z = 8
Mr = 274.74	F(000) = 1152
Orthorhombic, Pbca	Dx = 1.347 Mg m−3
Hall symbol: -P 2ac 2ab	Mo Kα radiation, λ = 0.71073 Å
a = 7.411 (5) Å	µ = 0.28 mm−1
b = 12.314 (5) Å	T = 293 K
c = 29.684 (5) Å	Block, yellow
V = 2709 (2) Å3	0.03 × 0.02 × 0.01 mm

Bruker APEXII CCD diffractometer	1895 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.028
Graphite monochromator	θmax = 25.1°, θmin = 3.1°
phi and ω scans	h = −8→8
14319 measured reflections	k = −13→14
2346 independent reflections	l = −33→35

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0321P)2 + 1.9647P] where P = (Fo2 + 2Fc2)/3
2346 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl01	0.50194 (10)	0.14231 (6)	0.23931 (2)	0.0581 (2)
O002	0.7854 (3)	−0.17647 (13)	0.11151 (6)	0.0568 (6)
N1	0.6988 (2)	0.01773 (14)	0.07922 (6)	0.0368 (6)
N2	0.7096 (3)	0.22034 (16)	−0.12244 (6)	0.0488 (7)
C1	0.7045 (4)	−0.1285 (2)	0.18620 (8)	0.0527 (9)
C2	0.6370 (4)	−0.0540 (2)	0.21635 (8)	0.0508 (9)
C3	0.5870 (3)	0.04721 (19)	0.20103 (7)	0.0401 (7)
C4	0.6031 (3)	0.07596 (18)	0.15641 (7)	0.0377 (7)
C5	0.6693 (3)	0.00046 (17)	0.12564 (7)	0.0336 (6)
C6	0.7202 (3)	−0.10202 (19)	0.14121 (7)	0.0415 (8)
C7	0.6153 (3)	0.09407 (18)	0.05884 (7)	0.0353 (7)
C8	0.6406 (3)	0.12185 (17)	0.01192 (7)	0.0326 (7)
C9	0.5587 (3)	0.21453 (18)	−0.00490 (7)	0.0404 (7)
C10	0.5801 (3)	0.24837 (19)	−0.04866 (7)	0.0409 (7)
C11	0.6858 (3)	0.18775 (17)	−0.07873 (7)	0.0351 (7)
C12	0.7676 (3)	0.09286 (18)	−0.06181 (7)	0.0384 (7)
C13	0.7462 (3)	0.06157 (17)	−0.01784 (7)	0.0364 (7)
C14	0.6269 (4)	0.3194 (2)	−0.13863 (8)	0.0584 (10)
C15	0.7819 (4)	0.1475 (2)	−0.15601 (7)	0.0542 (9)
H1	0.73970	−0.19690	0.19620	0.0630*
H02	0.78730	−0.15000	0.08620	0.0850*
H2	0.62520	−0.07170	0.24670	0.0610*
H4	0.57000	0.14510	0.14690	0.0450*
H7	0.53250	0.13460	0.07530	0.0420*
H9	0.48630	0.25550	0.01420	0.0480*
H10	0.52420	0.31180	−0.05840	0.0490*
H12	0.83780	0.05050	−0.08090	0.0460*
H13	0.80310	−0.00110	−0.00770	0.0440*
H14A	0.65710	0.32970	−0.16980	0.0870*
H14B	0.67050	0.37980	−0.12130	0.0870*
H14C	0.49830	0.31420	−0.13550	0.0870*
H15A	0.78840	0.18430	−0.18450	0.0810*
H15B	0.70480	0.08520	−0.15870	0.0810*
H15C	0.90060	0.12460	−0.14720	0.0810*

	U11	U22	U33	U12	U13	U23
Cl01	0.0648 (4)	0.0729 (5)	0.0366 (3)	0.0025 (4)	0.0062 (3)	−0.0031 (3)
O002	0.0736 (13)	0.0446 (10)	0.0522 (10)	0.0160 (9)	−0.0035 (9)	0.0047 (8)
N1	0.0422 (11)	0.0344 (10)	0.0337 (9)	−0.0028 (9)	−0.0004 (8)	0.0040 (8)
N2	0.0689 (15)	0.0490 (12)	0.0285 (9)	−0.0023 (11)	0.0040 (10)	−0.0006 (9)
C1	0.0608 (17)	0.0469 (14)	0.0504 (14)	0.0015 (13)	−0.0106 (13)	0.0188 (12)
C2	0.0555 (16)	0.0617 (16)	0.0351 (12)	−0.0045 (14)	−0.0066 (11)	0.0156 (12)
C3	0.0366 (12)	0.0506 (14)	0.0330 (11)	−0.0062 (11)	−0.0021 (10)	0.0026 (10)
C4	0.0390 (13)	0.0384 (12)	0.0357 (11)	−0.0042 (10)	−0.0017 (10)	0.0077 (10)
C5	0.0324 (11)	0.0345 (11)	0.0340 (11)	−0.0054 (10)	−0.0033 (9)	0.0059 (9)
C6	0.0397 (13)	0.0415 (13)	0.0432 (13)	0.0000 (11)	−0.0065 (11)	0.0053 (11)
C7	0.0362 (12)	0.0368 (12)	0.0328 (11)	−0.0023 (10)	0.0025 (10)	−0.0003 (9)
C8	0.0335 (12)	0.0328 (11)	0.0315 (11)	−0.0023 (10)	0.0001 (9)	0.0001 (9)
C9	0.0445 (14)	0.0431 (13)	0.0335 (11)	0.0100 (11)	0.0058 (10)	−0.0018 (10)
C10	0.0485 (14)	0.0392 (13)	0.0350 (11)	0.0100 (11)	−0.0009 (10)	0.0035 (10)
C11	0.0392 (13)	0.0359 (12)	0.0303 (11)	−0.0084 (10)	−0.0005 (9)	−0.0024 (9)
C12	0.0437 (13)	0.0360 (12)	0.0356 (11)	−0.0011 (11)	0.0060 (10)	−0.0084 (10)
C13	0.0408 (13)	0.0287 (11)	0.0398 (12)	−0.0003 (10)	−0.0008 (10)	0.0006 (9)
C14	0.084 (2)	0.0552 (16)	0.0359 (13)	−0.0045 (15)	−0.0009 (13)	0.0107 (11)
C15	0.0613 (17)	0.0677 (17)	0.0335 (12)	−0.0105 (14)	0.0077 (12)	−0.0066 (12)

Cl01—C3	1.749 (3)	C10—C11	1.403 (3)
O002—C6	1.361 (3)	C11—C12	1.409 (3)
O002—H02	0.8200	C12—C13	1.370 (3)
N1—C7	1.278 (3)	C1—H1	0.9300
N1—C5	1.411 (3)	C2—H2	0.9300
N2—C11	1.370 (3)	C4—H4	0.9300
N2—C15	1.444 (3)	C7—H7	0.9300
N2—C14	1.447 (3)	C9—H9	0.9300
C1—C6	1.380 (3)	C10—H10	0.9300
C1—C2	1.376 (4)	C12—H12	0.9300
C2—C3	1.378 (4)	C13—H13	0.9300
C3—C4	1.376 (3)	C14—H14A	0.9600
C4—C5	1.393 (3)	C14—H14B	0.9600
C5—C6	1.396 (3)	C14—H14C	0.9600
C7—C8	1.446 (3)	C15—H15A	0.9600
C8—C13	1.394 (3)	C15—H15B	0.9600
C8—C9	1.386 (3)	C15—H15C	0.9600
C9—C10	1.373 (3)
Cl01···H15Ai	3.1200	H4···O002ii	2.6600
Cl01···H1ii	3.0400	H7···C4	2.5700
Cl01···H14Aiii	2.9500	H7···H4	2.1500
O002···N1	2.655 (3)	H7···H9	2.3700
O002···C10iv	3.406 (4)	H7···O002ii	2.9000
O002···C7v	3.312 (4)	H9···H7	2.3700
O002···H14Civ	2.7900	H9···C8i	3.0700
O002···H15Cvi	2.6400	H9···C11i	3.0200
O002···H4v	2.6600	H9···C12i	2.8500
O002···H7v	2.9000	H9···C13i	2.8700
N1···O002	2.655 (3)	H10···C14	2.5000
N1···H02	2.1800	H10···H14B	2.3200
N1···H13	2.7000	H10···H14C	2.3000
C7···C13iv	3.512 (4)	H12···C15	2.5600
C7···O002ii	3.312 (4)	H12···H15B	2.5500
C10···O002iv	3.406 (4)	H12···H15C	2.2200
C13···C7iv	3.512 (4)	H12···H14Bv	2.4200
C2···H15Biv	3.0800	H13···N1	2.7000
C3···H15Biv	2.9900	H14A···H15A	2.0800
C4···H15Biv	3.0200	H14A···Cl01ix	2.9500
C4···H7	2.5700	H14B···C10	2.7800
C6···H15Cvi	2.8300	H14B···H10	2.3200
C6···H14Civ	3.0800	H14B···H12ii	2.4200
C7···H4	2.7100	H14C···C10	2.7700
C8···H9vii	3.0700	H14C···H10	2.3000
C10···H14B	2.7800	H14C···O002iv	2.7900
C10···H14C	2.7700	H14C···C6iv	3.0800
C11···H9vii	3.0200	H15A···H14A	2.0800
C12···H15B	2.9200	H15A···H2x	2.5500
C12···H9vii	2.8500	H15A···Cl01vii	3.1200
C12···H15C	2.7500	H15B···C12	2.9200
C13···H9vii	2.8700	H15B···H12	2.5500
C14···H10	2.5000	H15B···C2iv	3.0800
C15···H12	2.5600	H15B···C3iv	2.9900
H1···Cl01v	3.0400	H15B···C4iv	3.0200
H02···N1	2.1800	H15C···C12	2.7500
H2···H15Aviii	2.5500	H15C···H12	2.2200
H4···C7	2.7100	H15C···O002vi	2.6400
H4···H7	2.1500	H15C···C6vi	2.8300
C6—O002—H02	109.00	C2—C1—H1	120.00
C5—N1—C7	119.88 (18)	C6—C1—H1	120.00
C11—N2—C14	120.47 (19)	C1—C2—H2	120.00
C14—N2—C15	116.85 (18)	C3—C2—H2	120.00
C11—N2—C15	121.31 (19)	C3—C4—H4	120.00
C2—C1—C6	120.2 (2)	C5—C4—H4	120.00
C1—C2—C3	119.1 (2)	N1—C7—H7	118.00
Cl01—C3—C4	118.96 (18)	C8—C7—H7	118.00
C2—C3—C4	121.8 (2)	C8—C9—H9	119.00
Cl01—C3—C2	119.23 (17)	C10—C9—H9	119.00
C3—C4—C5	119.3 (2)	C9—C10—H10	120.00
N1—C5—C4	126.47 (19)	C11—C10—H10	120.00
N1—C5—C6	114.69 (18)	C11—C12—H12	119.00
C4—C5—C6	118.79 (19)	C13—C12—H12	119.00
O002—C6—C5	119.38 (19)	C8—C13—H13	119.00
C1—C6—C5	120.8 (2)	C12—C13—H13	119.00
O002—C6—C1	119.9 (2)	N2—C14—H14A	109.00
N1—C7—C8	124.6 (2)	N2—C14—H14B	109.00
C7—C8—C13	123.85 (19)	N2—C14—H14C	109.00
C9—C8—C13	117.13 (19)	H14A—C14—H14B	110.00
C7—C8—C9	119.01 (19)	H14A—C14—H14C	109.00
C8—C9—C10	122.7 (2)	H14B—C14—H14C	110.00
C9—C10—C11	120.3 (2)	N2—C15—H15A	109.00
N2—C11—C10	121.3 (2)	N2—C15—H15B	109.00
N2—C11—C12	121.7 (2)	N2—C15—H15C	110.00
C10—C11—C12	117.05 (19)	H15A—C15—H15B	109.00
C11—C12—C13	121.5 (2)	H15A—C15—H15C	109.00
C8—C13—C12	121.3 (2)	H15B—C15—H15C	109.00
C7—N1—C5—C4	−21.8 (3)	N1—C5—C6—O002	−2.4 (3)
C7—N1—C5—C6	161.0 (2)	N1—C5—C6—C1	177.8 (2)
C5—N1—C7—C8	177.4 (2)	C4—C5—C6—O002	−179.9 (2)
C14—N2—C11—C10	0.6 (3)	C4—C5—C6—C1	0.3 (3)
C14—N2—C11—C12	−178.7 (2)	N1—C7—C8—C9	−172.2 (2)
C15—N2—C11—C10	−165.6 (2)	N1—C7—C8—C13	6.7 (4)
C15—N2—C11—C12	15.1 (3)	C7—C8—C9—C10	178.1 (2)
C6—C1—C2—C3	−0.5 (4)	C13—C8—C9—C10	−0.9 (3)
C2—C1—C6—O002	−179.4 (2)	C7—C8—C13—C12	−178.9 (2)
C2—C1—C6—C5	0.4 (4)	C9—C8—C13—C12	−0.1 (3)
C1—C2—C3—Cl01	−179.8 (2)	C8—C9—C10—C11	1.1 (3)
C1—C2—C3—C4	−0.2 (4)	C9—C10—C11—N2	−179.7 (2)
Cl01—C3—C4—C5	−179.48 (17)	C9—C10—C11—C12	−0.4 (3)
C2—C3—C4—C5	0.9 (4)	N2—C11—C12—C13	178.8 (2)
C3—C4—C5—N1	−178.1 (2)	C10—C11—C12—C13	−0.5 (3)
C3—C4—C5—C6	−1.0 (3)	C11—C12—C13—C8	0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg2i	0.93	2.70	3.533 (3)	150
C15—H15B···Cg1iv	0.96	2.76	3.581 (4)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cg2i	0.93	2.70	3.533 (3)	150
C15—H15B⋯Cg1ii	0.96	2.76	3.581 (4)	142

Symmetry codes: (i) ; (ii) .