(E)-1-[(2-Chloro-4-nitro­phenyl­imino)­meth­yl]naphthalen-2-ol

Wang, J.; Zhang, J.; Yang, P.; Chen, T.

doi:10.1107/S1600536811021374

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1618

doi:10.1107/S1600536811021374

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(E)-1-[(2-Chloro-4-nitrophenylimino)methyl]naphthalen-2-ol

Juangang Wang,^a ^* Jun Zhang,^a Peipei Yang ^a and Tiedan Chen ^a

^aCollege of Chemistry and Materials Science, Huaibei Normal University, Xiangshan, Huaibei 235000, People's Republic of China
^*Correspondence e-mail: 363019204@qq.com

(Received 16 May 2011; accepted 2 June 2011; online 11 June 2011)

In the title compound, C₁₇H₁₁ClN₂O₃, an intramolecular O—H⋯N hydrogen bond influences the molecular conformation; the naphthol system and the substituted benzene ring form a dihedral angle of 3.5 (1)°. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link molecules into chains in the [010] direction The crystal packing exhibits π–π interactions between the aromatic rings from the neighbouring molecules, with a centroid–centroid distance of 3.566 (7) Å.

Related literature

For general background to Schiff bases, see: Caligaris et al. (1972 ); Salman et al. (1990 ); Popovic et al. (2001 ); Garnovskii et al. (1993 ); Pyrz et al. (1985 ). For related structures, see: Burgess et al. (1999 ); Gayathri et al. (2007 ).

Experimental

Crystal data

C₁₇H₁₁ClN₂O₃
M_r = 326.73
Monoclinic, P 2₁ /c
a = 7.0530 (8) Å
b = 12.8699 (13) Å
c = 15.7701 (17) Å
β = 98.180 (1)°
V = 1416.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 298 K
0.38 × 0.13 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.899, T_max = 0.972
7115 measured reflections
2506 independent reflections
826 reflections with I > 2σ(I)
R_int = 0.195

Refinement

R[F² > 2σ(F²)] = 0.080
wR(F²) = 0.185
S = 0.92
2506 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.81	2.547 (5)	149
C8—H8⋯O3ⁱ	0.93	2.50	3.392 (5)	160
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{7\over 2}}]$ .

Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811021374/cv5095sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021374/cv5095Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811021374/cv5095Isup3.cml

checkCIF report

Comment top

Schiff base ligands play a vital role in coordination chemistry due to their metal binding ability (Garnovskii et al., 1993). In addition, Schiff bases and their metal complexes have wide applications in biological systems (Pyrz et al., 1985). 2-Hydroxy Schiff bases are formed by reactions of salicylaldehyde and 2-hydroxy-1-naphthaldehyde with various amines (Caligaris et al., 1972). In contrast to salicylaldimine derivatives, the Schiff bases of 2-hydroxy-1-naphthaldehyde have been rarely investigated (Salman et al., 1990; Popovic et al., 2001). Herewith we present the title compound (I), derived from 2-hydroxy-1-naphthaldehyde.

In (I) (Fig. 1), the bond lengths and angles are normal and comparable with those observed for unsubstituted analogues (Burgess et al., 1999; Gayathri et al., 2007). Due to intramolecular O—H···N hydrogen bond (Table 1), the C—N=C—C torsion angle (between the phenol and benzene rings) is close to 180° with the value of 178.4 (7)°. In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into chains in [010]. The crystal packing exhibits π-π interactions between the aromatic rings from the neighbouring molecules with centroid-centroid distance of 3.566 (7) Å.

Related literature top

For general background to Schiff bases, see: Caligaris et al. (1972); Salman et al. (1990); Popovic et al. (2001); Garnovskii et al. (1993); Pyrz et al. (1985). For related structures, see: Burgess et al. (1999); Gayathri et al. (2007).

Experimental top

20 ml of methanol, 2-hydroxy-1-naphthaldehyde (0.172 g, 1 mmol), 2-chloro-4-nitrobenzenamine (0.172 g, 1 mmol) and four drops of acetic acid were added to a 50 ml round bottom flask with a magnetic stir bar. The solution was refluxed for 1.5 h until it was a bright orange color. The solution was then gravity filtered hot and allowed to slowly cool, yielding 0.268 g (78% yield) of bright orange-yellow needle-like crystals.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of (I) with displacement ellipsoids shown at 30% probability level.

(E)-1-[(2-Chloro-4-nitrophenylimino)methyl]naphthalen-2-ol top

Crystal data top

C₁₇H₁₁ClN₂O₃	F(000) = 672
M_r = 326.73	D_x = 1.532 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.0530 (8) Å	Cell parameters from 381 reflections
b = 12.8699 (13) Å	θ = 2.6–17.6°
c = 15.7701 (17) Å	µ = 0.29 mm⁻¹
β = 98.180 (1)°	T = 298 K
V = 1416.9 (3) Å³	Needle-like, orange
Z = 4	0.38 × 0.13 × 0.10 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2506 independent reflections
Radiation source: fine-focus sealed tube	826 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.195
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→8
T_min = 0.899, T_max = 0.972	k = −15→13
7115 measured reflections	l = −18→16

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.185	H-atom parameters constrained
S = 0.92	w = 1/[σ²(F_o²) + (0.0279P)²] where P = (F_o² + 2F_c²)/3
2506 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₇H₁₁ClN₂O₃	V = 1416.9 (3) Å³
M_r = 326.73	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.0530 (8) Å	µ = 0.29 mm⁻¹
b = 12.8699 (13) Å	T = 298 K
c = 15.7701 (17) Å	0.38 × 0.13 × 0.10 mm
β = 98.180 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2506 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	826 reflections with I > 2σ(I)
T_min = 0.899, T_max = 0.972	R_int = 0.195
7115 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.080	0 restraints
wR(F²) = 0.185	H-atom parameters constrained
S = 0.92	Δρ_max = 0.30 e Å⁻³
2506 reflections	Δρ_min = −0.33 e Å⁻³
208 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.2762 (3)	0.18899 (12)	1.41156 (10)	0.0618 (7)
N1	0.2572 (8)	0.4009 (4)	1.4787 (3)	0.0468 (16)
N2	0.5023 (10)	0.0960 (4)	1.7252 (4)	0.065 (2)
O1	0.1367 (7)	0.4326 (3)	1.3208 (3)	0.0730 (18)
H1	0.1721	0.3999	1.3648	0.110*
O2	0.4914 (9)	0.0043 (4)	1.7011 (3)	0.0845 (19)
O3	0.5720 (9)	0.1209 (3)	1.7972 (3)	0.086 (2)
C1	0.2399 (9)	0.5024 (5)	1.4905 (4)	0.0436 (19)
H1A	0.2700	0.5291	1.5456	0.052*
C2	0.1788 (9)	0.5698 (4)	1.4240 (4)	0.0441 (19)
C3	0.1298 (11)	0.5312 (5)	1.3387 (4)	0.058 (2)
C4	0.0772 (10)	0.6039 (5)	1.2683 (4)	0.060 (2)
H4	0.0473	0.5789	1.2127	0.072*
C5	0.0714 (10)	0.7060 (5)	1.2830 (4)	0.060 (2)
H5	0.0401	0.7506	1.2366	0.072*
C6	0.1122 (9)	0.7501 (4)	1.3681 (4)	0.0421 (18)
C7	0.1664 (9)	0.6842 (4)	1.4387 (4)	0.0441 (19)
C8	0.2087 (9)	0.7311 (5)	1.5193 (4)	0.052 (2)
H8	0.2425	0.6894	1.5672	0.062*
C9	0.2017 (10)	0.8362 (5)	1.5295 (5)	0.054 (2)
H9	0.2331	0.8656	1.5836	0.065*
C10	0.1475 (10)	0.8988 (5)	1.4589 (5)	0.056 (2)
H10	0.1407	0.9704	1.4661	0.068*
C11	0.1037 (10)	0.8572 (4)	1.3787 (5)	0.054 (2)
H11	0.0687	0.9002	1.3316	0.065*
C12	0.3140 (9)	0.3279 (4)	1.5437 (4)	0.0400 (18)
C13	0.3278 (9)	0.2238 (5)	1.5197 (4)	0.0413 (18)
C14	0.3845 (10)	0.1468 (4)	1.5788 (4)	0.046 (2)
H14	0.3892	0.0775	1.5624	0.055*
C15	0.4332 (9)	0.1761 (5)	1.6617 (4)	0.0444 (18)
C16	0.4224 (9)	0.2773 (5)	1.6893 (4)	0.047 (2)
H16	0.4532	0.2941	1.7470	0.057*
C17	0.3651 (9)	0.3523 (4)	1.6296 (4)	0.0426 (19)
H17	0.3604	0.4212	1.6470	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0977 (16)	0.0460 (10)	0.0362 (10)	−0.0018 (11)	−0.0089 (10)	−0.0058 (8)
N1	0.064 (4)	0.024 (3)	0.048 (4)	0.000 (3)	−0.005 (3)	0.003 (3)
N2	0.103 (6)	0.042 (4)	0.043 (4)	0.001 (4)	−0.013 (4)	0.005 (3)
O1	0.134 (5)	0.037 (3)	0.039 (3)	−0.007 (3)	−0.019 (3)	−0.001 (2)
O2	0.144 (5)	0.043 (3)	0.060 (4)	0.006 (3)	−0.007 (4)	0.004 (3)
O3	0.148 (6)	0.055 (3)	0.040 (3)	0.009 (3)	−0.036 (4)	0.001 (2)
C1	0.051 (5)	0.036 (4)	0.042 (4)	−0.006 (3)	0.002 (4)	0.002 (3)
C2	0.053 (5)	0.037 (4)	0.040 (4)	−0.001 (3)	−0.002 (4)	0.000 (3)
C3	0.084 (6)	0.033 (4)	0.051 (5)	0.007 (4)	−0.008 (5)	−0.003 (3)
C4	0.094 (7)	0.045 (4)	0.032 (4)	0.000 (4)	−0.025 (4)	−0.002 (3)
C5	0.077 (6)	0.048 (5)	0.049 (5)	−0.005 (4)	−0.013 (4)	0.016 (4)
C6	0.050 (5)	0.035 (4)	0.041 (4)	0.005 (3)	0.004 (4)	0.003 (3)
C7	0.051 (5)	0.032 (4)	0.045 (4)	−0.003 (3)	−0.007 (4)	−0.004 (3)
C8	0.062 (5)	0.047 (4)	0.043 (5)	−0.002 (4)	−0.003 (4)	0.008 (3)
C9	0.060 (6)	0.045 (5)	0.053 (5)	0.001 (4)	−0.003 (4)	−0.015 (4)
C10	0.067 (6)	0.030 (4)	0.072 (6)	0.003 (4)	0.008 (5)	−0.010 (4)
C11	0.059 (5)	0.028 (4)	0.070 (6)	0.005 (3)	−0.009 (5)	0.001 (4)
C12	0.046 (5)	0.036 (4)	0.038 (4)	−0.003 (3)	0.006 (4)	−0.003 (3)
C13	0.051 (5)	0.037 (4)	0.034 (4)	−0.003 (3)	0.002 (4)	−0.008 (3)
C14	0.070 (6)	0.029 (4)	0.035 (4)	−0.007 (3)	−0.007 (4)	−0.004 (3)
C15	0.055 (5)	0.042 (4)	0.033 (4)	−0.006 (4)	−0.004 (4)	0.008 (3)
C16	0.062 (5)	0.045 (4)	0.031 (4)	−0.004 (4)	−0.002 (4)	−0.003 (3)
C17	0.053 (5)	0.032 (4)	0.041 (4)	0.001 (3)	−0.001 (4)	−0.008 (3)

Geometric parameters (Å, º) top

Cl1—C13	1.751 (6)	C6—C7	1.408 (8)
N1—C1	1.328 (7)	C7—C8	1.400 (8)
N1—C12	1.406 (7)	C8—C9	1.364 (8)
N2—O3	1.215 (6)	C8—H8	0.9300
N2—O2	1.239 (6)	C9—C10	1.383 (9)
N2—C15	1.471 (7)	C9—H9	0.9300
O1—C3	1.303 (7)	C10—C11	1.368 (9)
O1—H1	0.8200	C10—H10	0.9300
C1—C2	1.383 (8)	C11—H11	0.9300
C1—H1A	0.9300	C12—C17	1.387 (8)
C2—C3	1.429 (8)	C12—C13	1.399 (7)
C2—C7	1.495 (8)	C13—C14	1.380 (7)
C3—C4	1.458 (8)	C14—C15	1.357 (8)
C4—C5	1.335 (8)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.379 (8)
C5—C6	1.449 (8)	C16—C17	1.370 (7)
C5—H5	0.9300	C16—H16	0.9300
C6—C11	1.391 (7)	C17—H17	0.9300

C1—N1—C12	125.2 (5)	C7—C8—H8	119.0
O3—N2—O2	122.5 (5)	C8—C9—C10	119.5 (7)
O3—N2—C15	120.1 (6)	C8—C9—H9	120.2
O2—N2—C15	117.3 (6)	C10—C9—H9	120.2
C3—O1—H1	109.5	C11—C10—C9	121.1 (6)
N1—C1—C2	122.4 (6)	C11—C10—H10	119.4
N1—C1—H1A	118.8	C9—C10—H10	119.4
C2—C1—H1A	118.8	C10—C11—C6	119.3 (7)
C1—C2—C3	120.3 (6)	C10—C11—H11	120.3
C1—C2—C7	121.2 (6)	C6—C11—H11	120.3
C3—C2—C7	118.5 (5)	C17—C12—C13	117.5 (5)
O1—C3—C2	122.1 (6)	C17—C12—N1	124.7 (5)
O1—C3—C4	118.3 (6)	C13—C12—N1	117.8 (6)
C2—C3—C4	119.6 (6)	C14—C13—C12	122.0 (6)
C5—C4—C3	120.7 (6)	C14—C13—Cl1	118.2 (5)
C5—C4—H4	119.6	C12—C13—Cl1	119.7 (5)
C3—C4—H4	119.6	C15—C14—C13	117.3 (6)
C4—C5—C6	122.6 (6)	C15—C14—H14	121.3
C4—C5—H5	118.7	C13—C14—H14	121.3
C6—C5—H5	118.7	C14—C15—C16	123.3 (6)
C11—C6—C7	120.9 (6)	C14—C15—N2	118.3 (6)
C11—C6—C5	119.5 (6)	C16—C15—N2	118.3 (6)
C7—C6—C5	119.5 (5)	C17—C16—C15	118.2 (6)
C8—C7—C6	117.2 (6)	C17—C16—H16	120.9
C8—C7—C2	123.8 (6)	C15—C16—H16	120.9
C6—C7—C2	119.0 (5)	C16—C17—C12	121.5 (6)
C9—C8—C7	121.9 (6)	C16—C17—H17	119.2
C9—C8—H8	119.0	C12—C17—H17	119.2

C12—N1—C1—C2	−178.4 (7)	C8—C9—C10—C11	−1.1 (11)
N1—C1—C2—C3	0.6 (11)	C9—C10—C11—C6	0.6 (12)
N1—C1—C2—C7	−178.1 (6)	C7—C6—C11—C10	−0.5 (11)
C1—C2—C3—O1	1.4 (12)	C5—C6—C11—C10	−178.2 (7)
C7—C2—C3—O1	−179.9 (6)	C1—N1—C12—C17	−1.8 (11)
C1—C2—C3—C4	−176.2 (7)	C1—N1—C12—C13	−179.0 (6)
C7—C2—C3—C4	2.5 (11)	C17—C12—C13—C14	1.9 (10)
O1—C3—C4—C5	−178.7 (7)	N1—C12—C13—C14	179.2 (6)
C2—C3—C4—C5	−1.0 (11)	C17—C12—C13—Cl1	−177.0 (5)
C3—C4—C5—C6	−1.4 (11)	N1—C12—C13—Cl1	0.4 (8)
C4—C5—C6—C11	179.9 (7)	C12—C13—C14—C15	−2.1 (11)
C4—C5—C6—C7	2.2 (11)	Cl1—C13—C14—C15	176.7 (5)
C11—C6—C7—C8	0.8 (10)	C13—C14—C15—C16	2.2 (11)
C5—C6—C7—C8	178.5 (6)	C13—C14—C15—N2	−177.3 (6)
C11—C6—C7—C2	−178.3 (6)	O3—N2—C15—C14	169.8 (7)
C5—C6—C7—C2	−0.6 (10)	O2—N2—C15—C14	−8.1 (10)
C1—C2—C7—C8	−2.0 (10)	O3—N2—C15—C16	−9.8 (11)
C3—C2—C7—C8	179.3 (7)	O2—N2—C15—C16	172.3 (7)
C1—C2—C7—C6	177.0 (7)	C14—C15—C16—C17	−2.0 (11)
C3—C2—C7—C6	−1.7 (10)	N2—C15—C16—C17	177.5 (6)
C6—C7—C8—C9	−1.2 (11)	C15—C16—C17—C12	1.7 (10)
C2—C7—C8—C9	177.7 (6)	C13—C12—C17—C16	−1.6 (10)
C7—C8—C9—C10	1.4 (11)	N1—C12—C17—C16	−178.8 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.81	2.547 (5)	149
C8—H8···O3ⁱ	0.93	2.50	3.392 (5)	160

Symmetry code: (i) −x+1, y+1/2, −z+7/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₁ClN₂O₃
M_r	326.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.0530 (8), 12.8699 (13), 15.7701 (17)
β (°)	98.180 (1)
V (Å³)	1416.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.38 × 0.13 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.899, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	7115, 2506, 826
R_int	0.195
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.185, 0.92
No. of reflections	2506
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.33

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.820	1.810	2.547 (5)	148.64
C8—H8···O3ⁱ	0.930	2.503	3.392 (5)	160.04

Symmetry code: (i) −x+1, y+1/2, −z+7/2.

Acknowledgements

Financial support from Huaibei Normal University is gratefully acknowledged.

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