4-Chloro-2-[(E)-2-(4-methoxy­phen­yl)ethyl­imino­meth­yl]phenol

Yaeghoobi, M.; Rahman, N.A.; Ng, S.W.

doi:10.1107/S1600536809013348

organic compounds

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Volume 65| Part 5| May 2009| Page o1070

doi:10.1107/S1600536809013348

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4-Chloro-2-[(E)-2-(4-methoxyphenyl)ethyliminomethyl]phenol

Marzieh Yaeghoobi,^a Noorsaadah Abdul Rahman ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 7 April 2009; accepted 8 April 2009; online 18 April 2009)

In the title Schiff base, C₁₆H₁₆ClNO₂, the 2-(4-methoxyphenyl)ethyl (CH₃OC₆H₄CH₂CH₂–; r.m.s. deviation = 0.10 Å) and 4-chloro-2-(iminomethyl)phenol (N=CHC₆H₃ClOH; 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_r = 289.75
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.099
S = 1.03
3036 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.28 e Å⁻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)

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 ).

Supporting information

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

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

checkCIF report

Related literature top

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 top

2-(4-Methoxyphenyl)ethylamine (0.30 g, 2 mmol) and 5-chlorosalicylaldehyde (0.31 g, 2 mmol) were heated in ethanol (20 ml) for 1 h. The solution was set aside for the growth of crystals.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).

Figures top

Fig. 1. Thermal ellipsoid plot of C₁₆H₁₆ClNO₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

4-Chloro-2-[(E)-2-(4-methoxyphenyl)ethyliminomethyl]phenol top

Crystal data top

C₁₆H₁₆ClNO₂	Z = 2
M_r = 289.75	F(000) = 304
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.033P)² + 0.4582P] where P = (F_o² + 2F_c²)/3
3036 reflections	(Δ/σ)_max = 0.001
186 parameters	Δρ_max = 0.28 e Å⁻³
1 restraint	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₆H₁₆ClNO₂	γ = 85.313 (2)°
M_r = 289.75	V = 692.65 (4) Å³
Triclinic, P1	Z = 2
a = 5.7610 (2) Å	Mo Kα radiation
b = 7.7115 (3) Å	µ = 0.28 mm⁻¹
c = 15.7814 (5) Å	T = 100 K
α = 82.420 (2)°	0.25 × 0.25 × 0.03 mm
β = 89.320 (2)°

Data collection top

Bruker SMART APEX diffractometer	3036 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2235 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.992	R_int = 0.025
5284 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	1 restraint
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.28 e Å⁻³
3036 reflections	Δρ_min = −0.28 e Å⁻³
186 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆ClNO₂
M_r	289.75
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.7610 (2), 7.7115 (3), 15.7814 (5)
α, β, γ (°)	82.420 (2), 89.320 (2), 85.313 (2)
V (Å³)	692.65 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.25 × 0.25 × 0.03

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.934, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	5284, 3036, 2235
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.099, 1.03
No. of reflections	3036
No. of parameters	186
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.28

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

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)

Acknowledgements

We thank the University of Malaya for supporting this study.

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