4-Chloro-2-[(E)-2-(4-methoxy-phen-yl)ethyl-imino-meth-yl]phenol.

In the title Schiff base, C(16)H(16)ClNO(2), the 2-(4-methoxy-phen-yl)ethyl (CH(3)OC(6)H(4)CH(2)CH(2)-; r.m.s. deviation = 0.10 Å) and 4-chloro-2-(imino-meth-yl)phenol (N=CHC(6)H(3)ClOH; r.m.s. deviation = 0.01 Å) portions are both essentially planar, the two parts being inclined at an angle of 61.8 (1)°. The hydroxy group forms a hydrogen bond to the imino N atom.

Related literature

The crystal structures of several Schiff bases derived by condensing aryl-2-ethyl­amines and substituted salicylaldehydes have been reported; see: Chatziefthimiou et al. (2006 ▶); Chohan et al. (2008 ▶); Coombs et al. (2005 ▶); Li et al. (2006 ▶); Räisänen et al. (2007 ▶).

Experimental

Crystal data

C16H16ClNO2

M = 289.75

Triclinic,

a = 5.7610 (2) Å

b = 7.7115 (3) Å

c = 15.7814 (5) Å

α = 82.420 (2)°

β = 89.320 (2)°

γ = 85.313 (2)°

V = 692.65 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 100 K

0.25 × 0.25 × 0.03 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.934, T max = 0.992

5284 measured reflections

3036 independent reflections

2235 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.099

S = 1.03

3036 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013348/sj2612sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013348/sj2612Isup2.hkl

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

C16H16ClNO2	Z = 2
Mr = 289.75	F(000) = 304
Triclinic, P1	Dx = 1.389 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7610 (2) Å	Cell parameters from 1628 reflections
b = 7.7115 (3) Å	θ = 2.7–28.2°
c = 15.7814 (5) Å	µ = 0.28 mm−1
α = 82.420 (2)°	T = 100 K
β = 89.320 (2)°	Plate, yellow
γ = 85.313 (2)°	0.25 × 0.25 × 0.03 mm
V = 692.65 (4) Å3

Bruker SMART APEX diffractometer	3036 independent reflections
Radiation source: fine-focus sealed tube	2235 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.934, Tmax = 0.992	k = −10→9
5284 measured reflections	l = −20→20

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.033P)2 + 0.4582P] where P = (Fo2 + 2Fc2)/3
3036 reflections	(Δ/σ)max = 0.001
186 parameters	Δρmax = 0.28 e Å−3
1 restraint	Δρmin = −0.28 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.72711 (10)	0.19401 (7)	0.02737 (3)	0.02303 (15)
O1	0.4122 (3)	0.0304 (2)	0.38188 (9)	0.0209 (3)
H1	0.509 (4)	0.068 (4)	0.4137 (15)	0.042 (8)*
O2	0.9991 (2)	0.43513 (19)	0.88357 (8)	0.0184 (3)
N1	0.7683 (3)	0.1729 (2)	0.42911 (10)	0.0157 (4)
C1	0.4895 (3)	0.0673 (3)	0.30093 (12)	0.0147 (4)
C2	0.3616 (3)	0.0202 (3)	0.23431 (13)	0.0168 (4)
H2	0.2243	−0.0389	0.2465	0.020*
C3	0.4334 (4)	0.0592 (3)	0.15057 (13)	0.0177 (4)
H3	0.3449	0.0282	0.1053	0.021*
C4	0.6357 (4)	0.1440 (3)	0.13294 (12)	0.0161 (4)
C5	0.7667 (3)	0.1895 (3)	0.19782 (12)	0.0150 (4)
H5	0.9056	0.2460	0.1847	0.018*
C6	0.6960 (3)	0.1530 (2)	0.28272 (12)	0.0130 (4)
C7	0.8351 (3)	0.2023 (3)	0.35138 (12)	0.0139 (4)
H7	0.9757	0.2564	0.3381	0.017*
C8	0.9076 (3)	0.2214 (3)	0.49754 (12)	0.0157 (4)
H8A	1.0524	0.2691	0.4737	0.019*
H8B	0.9509	0.1165	0.5393	0.019*
C9	0.7660 (3)	0.3591 (3)	0.54177 (12)	0.0159 (4)
H9A	0.7698	0.4739	0.5056	0.019*
H9B	0.6019	0.3293	0.5451	0.019*
C10	0.8459 (3)	0.3790 (3)	0.63111 (12)	0.0142 (4)
C11	0.6936 (3)	0.4703 (3)	0.68291 (13)	0.0158 (4)
H11	0.5482	0.5219	0.6603	0.019*
C12	0.7501 (4)	0.4870 (3)	0.76572 (13)	0.0163 (4)
H12	0.6443	0.5498	0.7995	0.020*
C13	0.9625 (4)	0.4120 (3)	0.80025 (12)	0.0159 (4)
C14	1.1189 (4)	0.3236 (3)	0.75010 (12)	0.0152 (4)
H14	1.2652	0.2739	0.7726	0.018*
C15	1.0580 (3)	0.3086 (3)	0.66572 (13)	0.0156 (4)
H15	1.1654	0.2486	0.6314	0.019*
C16	1.2113 (4)	0.3563 (3)	0.92316 (13)	0.0212 (5)
H16A	1.2147	0.3805	0.9825	0.032*
H16B	1.3442	0.4054	0.8920	0.032*
H16C	1.2202	0.2292	0.9220	0.032*

	U11	U22	U33	U12	U13	U23
Cl1	0.0271 (3)	0.0286 (3)	0.0145 (2)	−0.0072 (2)	0.0018 (2)	−0.0036 (2)
O1	0.0214 (8)	0.0262 (9)	0.0161 (7)	−0.0088 (7)	0.0029 (6)	−0.0026 (6)
O2	0.0195 (8)	0.0215 (8)	0.0141 (7)	−0.0005 (6)	−0.0014 (6)	−0.0023 (6)
N1	0.0174 (9)	0.0134 (9)	0.0164 (8)	−0.0008 (7)	−0.0022 (7)	−0.0024 (7)
C1	0.0144 (10)	0.0119 (10)	0.0172 (10)	0.0019 (8)	0.0020 (8)	−0.0011 (8)
C2	0.0130 (10)	0.0151 (10)	0.0226 (11)	−0.0015 (8)	−0.0012 (8)	−0.0033 (8)
C3	0.0171 (10)	0.0153 (10)	0.0211 (10)	−0.0005 (8)	−0.0045 (8)	−0.0046 (8)
C4	0.0181 (11)	0.0159 (10)	0.0139 (9)	0.0008 (8)	0.0014 (8)	−0.0016 (8)
C5	0.0144 (10)	0.0118 (10)	0.0185 (10)	−0.0008 (8)	−0.0001 (8)	−0.0011 (8)
C6	0.0121 (10)	0.0108 (10)	0.0157 (9)	0.0014 (8)	−0.0030 (8)	−0.0014 (8)
C7	0.0116 (10)	0.0109 (10)	0.0190 (10)	−0.0001 (8)	−0.0017 (8)	−0.0011 (8)
C8	0.0167 (10)	0.0141 (10)	0.0162 (10)	−0.0007 (8)	−0.0019 (8)	−0.0020 (8)
C9	0.0158 (10)	0.0136 (10)	0.0182 (10)	−0.0010 (8)	−0.0019 (8)	−0.0022 (8)
C10	0.0149 (10)	0.0112 (10)	0.0167 (10)	−0.0041 (8)	0.0014 (8)	−0.0010 (8)
C11	0.0119 (10)	0.0133 (10)	0.0217 (10)	−0.0006 (8)	−0.0001 (8)	−0.0014 (8)
C12	0.0148 (10)	0.0141 (10)	0.0199 (10)	0.0001 (8)	0.0033 (8)	−0.0030 (8)
C13	0.0203 (11)	0.0137 (10)	0.0138 (9)	−0.0050 (8)	0.0018 (8)	−0.0008 (8)
C14	0.0128 (10)	0.0147 (10)	0.0179 (10)	−0.0006 (8)	−0.0005 (8)	−0.0013 (8)
C15	0.0140 (10)	0.0143 (10)	0.0184 (10)	−0.0003 (8)	0.0023 (8)	−0.0027 (8)
C16	0.0228 (11)	0.0236 (12)	0.0172 (10)	−0.0034 (9)	−0.0027 (9)	−0.0022 (9)

Cl1—C4	1.745 (2)	C8—H8A	0.9900
O1—C1	1.350 (2)	C8—H8B	0.9900
O1—H1	0.849 (10)	C9—C10	1.519 (3)
O2—C13	1.371 (2)	C9—H9A	0.9900
O2—C16	1.432 (3)	C9—H9B	0.9900
N1—C7	1.278 (2)	C10—C15	1.384 (3)
N1—C8	1.458 (2)	C10—C11	1.403 (3)
C1—C2	1.394 (3)	C11—C12	1.375 (3)
C1—C6	1.415 (3)	C11—H11	0.9500
C2—C3	1.382 (3)	C12—C13	1.395 (3)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.390 (3)	C13—C14	1.388 (3)
C3—H3	0.9500	C14—C15	1.403 (3)
C4—C5	1.378 (3)	C14—H14	0.9500
C5—C6	1.395 (3)	C15—H15	0.9500
C5—H5	0.9500	C16—H16A	0.9800
C6—C7	1.463 (3)	C16—H16B	0.9800
C7—H7	0.9500	C16—H16C	0.9800
C8—C9	1.523 (3)
C1—O1—H1	106.3 (19)	C10—C9—C8	115.68 (17)
C13—O2—C16	117.54 (16)	C10—C9—H9A	108.4
C7—N1—C8	120.28 (17)	C8—C9—H9A	108.4
O1—C1—C2	118.87 (17)	C10—C9—H9B	108.4
O1—C1—C6	121.37 (17)	C8—C9—H9B	108.4
C2—C1—C6	119.77 (17)	H9A—C9—H9B	107.4
C3—C2—C1	120.33 (18)	C15—C10—C11	117.62 (18)
C3—C2—H2	119.8	C15—C10—C9	124.08 (18)
C1—C2—H2	119.8	C11—C10—C9	118.28 (18)
C2—C3—C4	119.71 (18)	C12—C11—C10	121.49 (19)
C2—C3—H3	120.1	C12—C11—H11	119.3
C4—C3—H3	120.1	C10—C11—H11	119.3
C5—C4—C3	120.97 (18)	C11—C12—C13	120.15 (18)
C5—C4—Cl1	119.05 (15)	C11—C12—H12	119.9
C3—C4—Cl1	119.98 (15)	C13—C12—H12	119.9
C4—C5—C6	120.20 (18)	O2—C13—C14	125.16 (19)
C4—C5—H5	119.9	O2—C13—C12	115.10 (17)
C6—C5—H5	119.9	C14—C13—C12	119.73 (18)
C5—C6—C1	119.01 (17)	C13—C14—C15	119.15 (19)
C5—C6—C7	120.01 (17)	C13—C14—H14	120.4
C1—C6—C7	120.98 (17)	C15—C14—H14	120.4
N1—C7—C6	120.31 (17)	C10—C15—C14	121.83 (18)
N1—C7—H7	119.8	C10—C15—H15	119.1
C6—C7—H7	119.8	C14—C15—H15	119.1
N1—C8—C9	108.99 (16)	O2—C16—H16A	109.5
N1—C8—H8A	109.9	O2—C16—H16B	109.5
C9—C8—H8A	109.9	H16A—C16—H16B	109.5
N1—C8—H8B	109.9	O2—C16—H16C	109.5
C9—C8—H8B	109.9	H16A—C16—H16C	109.5
H8A—C8—H8B	108.3	H16B—C16—H16C	109.5
O1—C1—C2—C3	178.70 (19)	C7—N1—C8—C9	117.2 (2)
C6—C1—C2—C3	−1.0 (3)	N1—C8—C9—C10	159.86 (16)
C1—C2—C3—C4	0.7 (3)	C8—C9—C10—C15	13.5 (3)
C2—C3—C4—C5	0.2 (3)	C8—C9—C10—C11	−164.78 (17)
C2—C3—C4—Cl1	−179.87 (16)	C15—C10—C11—C12	−1.2 (3)
C3—C4—C5—C6	−0.9 (3)	C9—C10—C11—C12	177.17 (18)
Cl1—C4—C5—C6	179.22 (16)	C10—C11—C12—C13	−0.2 (3)
C4—C5—C6—C1	0.6 (3)	C16—O2—C13—C14	−2.5 (3)
C4—C5—C6—C7	−179.72 (19)	C16—O2—C13—C12	178.17 (17)
O1—C1—C6—C5	−179.34 (18)	C11—C12—C13—O2	−179.27 (18)
C2—C1—C6—C5	0.3 (3)	C11—C12—C13—C14	1.4 (3)
O1—C1—C6—C7	1.0 (3)	O2—C13—C14—C15	179.56 (18)
C2—C1—C6—C7	−179.37 (18)	C12—C13—C14—C15	−1.2 (3)
C8—N1—C7—C6	179.71 (17)	C11—C10—C15—C14	1.5 (3)
C5—C6—C7—N1	178.33 (19)	C9—C10—C15—C14	−176.86 (18)
C1—C6—C7—N1	−2.0 (3)	C13—C14—C15—C10	−0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.85 (1)	1.79 (2)	2.567 (2)	152 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.85 (1)	1.79 (2)	2.567 (2)	152 (3)