(E)-1-[(2-Chloro-4-nitro-phenyl-imino)-meth-yl]naphthalen-2-ol.

In the title compound, C(17)H(11)ClN(2)O(3), an intra-molecular O-H⋯N hydrogen bond influences the mol-ecular conformation; the naphthol system and the substituted benzene ring form a dihedral angle of 3.5 (1)°. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link mol-ecules into chains in the [010] direction The crystal packing exhibits π-π inter-actions between the aromatic rings from the neighbouring mol-ecules, 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 = 326.73

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.185

S = 0.92

2506 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.33 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811021374/cv5095sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811021374/cv5095Isup3.cml

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

C17H11ClN2O3	F(000) = 672
Mr = 326.73	Dx = 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

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

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(Fo2) + (0.0279P)2] where P = (Fo2 + 2Fc2)/3
2506 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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.

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) .