3-Chloro-N'-[(2-hy-droxy-naphthalen-1-yl)methyl-idene]benzohydrazide.

The title compound, C(18)H(13)ClN(2)O(2), was prepared by the reaction of 2-hy-droxy-1-naphthaldehyde with 3-chloro-benzohydrazide in methanol. An intra-molecular O-H⋯N hydrogen bond influences the mol-ecular conformation; the benzene ring and naphthyl ring system form a dihedral angle of 17.1 (3)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains propagated in [101].

Related literature

For Schiff base compounds, see: Bessy et al. (2006 ▶); Podyachev et al. (2007 ▶); Raj & Kurup (2007 ▶); Pouralimardan et al. (2007 ▶); Bacchi et al. (2006 ▶); Dinda et al. (2002 ▶). For reference bond lengths, see: Allen et al. (1987 ▶). For details of the synthesis, see: Zhu (2010 ▶).

Experimental

Crystal data

C18H13ClN2O2

M = 324.75

Monoclinic,

a = 7.158 (2) Å

b = 30.886 (3) Å

c = 7.3733 (12) Å

β = 108.924 (2)°

V = 1541.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.950, T max = 0.955

8306 measured reflections

3288 independent reflections

1635 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.082

wR(F 2) = 0.161

S = 1.04

3288 reflections

212 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000912/cv5033sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000912/cv5033Isup2.hkl

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

C18H13ClN2O2	F(000) = 672
Mr = 324.75	Dx = 1.399 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.158 (2) Å	Cell parameters from 1332 reflections
b = 30.886 (3) Å	θ = 2.5–24.9°
c = 7.3733 (12) Å	µ = 0.26 mm−1
β = 108.924 (2)°	T = 298 K
V = 1541.9 (5) Å3	Block, colorless
Z = 4	0.20 × 0.20 × 0.18 mm

Bruker APEXII CCD area-detector diffractometer	3288 independent reflections
Radiation source: fine-focus sealed tube	1635 reflections with I > 2σ(I)
graphite	Rint = 0.062
ω scans	θmax = 27.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.950, Tmax = 0.955	k = −32→39
8306 measured reflections	l = −9→6

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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0443P)2 + 0.9339P] where P = (Fo2 + 2Fc2)/3
3288 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.24 e Å−3
1 restraint	Δρmin = −0.35 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	0.66632 (19)	0.05960 (4)	0.6685 (2)	0.0843 (5)
H2	0.696 (5)	0.2651 (13)	0.585 (3)	0.080*
N1	0.5796 (4)	0.28518 (9)	0.3225 (4)	0.0418 (8)
N2	0.6082 (5)	0.25640 (10)	0.4729 (4)	0.0427 (8)
O1	0.5149 (5)	0.30417 (9)	−0.0326 (4)	0.0597 (8)
H1	0.5222	0.2884	0.0590	0.090*
O2	0.4224 (4)	0.20537 (8)	0.2758 (4)	0.0533 (8)
C1	0.6241 (5)	0.35642 (11)	0.2236 (5)	0.0360 (9)
C2	0.5645 (5)	0.34493 (13)	0.0298 (6)	0.0445 (10)
C3	0.5567 (6)	0.37613 (15)	−0.1110 (6)	0.0562 (12)
H3	0.5214	0.3678	−0.2389	0.067*
C4	0.5998 (6)	0.41809 (15)	−0.0627 (7)	0.0586 (12)
H4	0.5922	0.4383	−0.1585	0.070*
C5	0.6560 (5)	0.43187 (12)	0.1296 (6)	0.0461 (10)
C6	0.6976 (6)	0.47585 (14)	0.1805 (7)	0.0609 (12)
H6	0.6873	0.4962	0.0848	0.073*
C7	0.7521 (7)	0.48893 (14)	0.3655 (8)	0.0706 (14)
H7	0.7803	0.5179	0.3966	0.085*
C8	0.7655 (7)	0.45872 (15)	0.5081 (7)	0.0716 (14)
H8	0.8008	0.4677	0.6351	0.086*
C9	0.7276 (6)	0.41613 (13)	0.4649 (6)	0.0545 (11)
H9	0.7406	0.3965	0.5640	0.065*
C10	0.6693 (5)	0.40069 (12)	0.2746 (6)	0.0398 (9)
C11	0.6392 (5)	0.32393 (12)	0.3679 (5)	0.0397 (9)
H11	0.6933	0.3313	0.4967	0.048*
C12	0.5277 (5)	0.21672 (12)	0.4356 (5)	0.0401 (9)
C13	0.5780 (5)	0.18679 (11)	0.6038 (5)	0.0375 (9)
C14	0.5923 (5)	0.14310 (12)	0.5659 (6)	0.0426 (9)
H14	0.5690	0.1337	0.4407	0.051*
C15	0.6411 (5)	0.11390 (12)	0.7143 (7)	0.0507 (11)
C16	0.6694 (6)	0.12736 (16)	0.8992 (7)	0.0620 (13)
H16	0.7013	0.1074	0.9989	0.074*
C17	0.6502 (6)	0.17043 (16)	0.9362 (6)	0.0609 (12)
H17	0.6675	0.1795	1.0609	0.073*
C18	0.6053 (5)	0.20038 (13)	0.7888 (6)	0.0476 (10)
H18	0.5936	0.2296	0.8143	0.057*

	U11	U22	U33	U12	U13	U23
Cl1	0.0781 (9)	0.0429 (7)	0.1416 (13)	0.0095 (6)	0.0490 (8)	0.0229 (7)
N1	0.0476 (19)	0.0348 (18)	0.040 (2)	−0.0005 (14)	0.0096 (15)	0.0034 (15)
N2	0.047 (2)	0.0355 (18)	0.0368 (19)	−0.0048 (15)	0.0017 (15)	0.0038 (16)
O1	0.078 (2)	0.0557 (19)	0.0442 (18)	−0.0086 (16)	0.0175 (16)	−0.0077 (14)
O2	0.0568 (17)	0.0465 (16)	0.0417 (17)	−0.0031 (13)	−0.0047 (13)	−0.0018 (13)
C1	0.0287 (19)	0.044 (2)	0.035 (2)	0.0038 (16)	0.0104 (16)	0.0037 (18)
C2	0.043 (2)	0.051 (3)	0.042 (2)	0.0003 (19)	0.0166 (19)	0.001 (2)
C3	0.062 (3)	0.074 (3)	0.032 (2)	0.003 (2)	0.015 (2)	0.011 (2)
C4	0.062 (3)	0.059 (3)	0.062 (3)	0.005 (2)	0.029 (2)	0.021 (2)
C5	0.040 (2)	0.044 (3)	0.057 (3)	0.0054 (18)	0.019 (2)	0.009 (2)
C6	0.059 (3)	0.044 (3)	0.082 (4)	0.005 (2)	0.026 (3)	0.020 (3)
C7	0.077 (3)	0.041 (3)	0.099 (4)	−0.007 (2)	0.035 (3)	−0.001 (3)
C8	0.089 (4)	0.058 (3)	0.072 (4)	−0.015 (3)	0.032 (3)	−0.011 (3)
C9	0.068 (3)	0.041 (3)	0.057 (3)	−0.008 (2)	0.025 (2)	−0.002 (2)
C10	0.034 (2)	0.041 (2)	0.045 (2)	0.0035 (16)	0.0134 (18)	0.004 (2)
C11	0.040 (2)	0.040 (2)	0.036 (2)	0.0024 (17)	0.0084 (17)	0.0051 (18)
C12	0.035 (2)	0.039 (2)	0.042 (2)	0.0006 (17)	0.0066 (18)	−0.0004 (19)
C13	0.035 (2)	0.036 (2)	0.039 (2)	−0.0010 (16)	0.0091 (17)	0.0009 (18)
C14	0.038 (2)	0.037 (2)	0.052 (3)	−0.0011 (17)	0.0130 (18)	0.006 (2)
C15	0.036 (2)	0.035 (2)	0.083 (4)	0.0019 (17)	0.021 (2)	0.011 (2)
C16	0.046 (3)	0.073 (3)	0.064 (3)	−0.002 (2)	0.014 (2)	0.031 (3)
C17	0.061 (3)	0.075 (3)	0.047 (3)	−0.006 (2)	0.018 (2)	0.010 (3)
C18	0.046 (2)	0.049 (2)	0.048 (3)	−0.0023 (19)	0.016 (2)	−0.003 (2)

Cl1—C15	1.732 (4)	C6—H6	0.9300
N1—C11	1.278 (4)	C7—C8	1.386 (6)
N1—N2	1.384 (4)	C7—H7	0.9300
N2—C12	1.344 (4)	C8—C9	1.360 (5)
N2—H2	0.90 (3)	C8—H8	0.9300
O1—C2	1.348 (4)	C9—C10	1.410 (5)
O1—H1	0.8200	C9—H9	0.9300
O2—C12	1.226 (4)	C11—H11	0.9300
C1—C2	1.398 (5)	C12—C13	1.494 (5)
C1—C10	1.427 (5)	C13—C18	1.379 (5)
C1—C11	1.441 (5)	C13—C14	1.388 (5)
C2—C3	1.404 (5)	C14—C15	1.373 (5)
C3—C4	1.353 (5)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.376 (6)
C4—C5	1.408 (5)	C16—C17	1.374 (6)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.415 (5)	C17—C18	1.383 (5)
C5—C10	1.419 (5)	C17—H17	0.9300
C6—C7	1.353 (6)	C18—H18	0.9300
C11—N1—N2	116.2 (3)	C8—C9—H9	118.9
C12—N2—N1	118.6 (3)	C10—C9—H9	118.9
C12—N2—H2	126 (3)	C9—C10—C5	116.5 (4)
N1—N2—H2	115 (3)	C9—C10—C1	123.7 (3)
C2—O1—H1	109.5	C5—C10—C1	119.8 (4)
C2—C1—C10	118.7 (3)	N1—C11—C1	121.3 (3)
C2—C1—C11	120.2 (3)	N1—C11—H11	119.3
C10—C1—C11	121.1 (3)	C1—C11—H11	119.3
O1—C2—C1	123.1 (3)	O2—C12—N2	123.1 (3)
O1—C2—C3	116.5 (4)	O2—C12—C13	121.9 (3)
C1—C2—C3	120.5 (4)	N2—C12—C13	115.0 (3)
C4—C3—C2	120.8 (4)	C18—C13—C14	119.9 (3)
C4—C3—H3	119.6	C18—C13—C12	123.4 (3)
C2—C3—H3	119.6	C14—C13—C12	116.6 (3)
C3—C4—C5	121.4 (4)	C15—C14—C13	119.6 (4)
C3—C4—H4	119.3	C15—C14—H14	120.2
C5—C4—H4	119.3	C13—C14—H14	120.2
C4—C5—C6	121.6 (4)	C14—C15—C16	120.6 (4)
C4—C5—C10	118.8 (4)	C14—C15—Cl1	119.8 (4)
C6—C5—C10	119.6 (4)	C16—C15—Cl1	119.6 (3)
C7—C6—C5	121.4 (4)	C17—C16—C15	119.8 (4)
C7—C6—H6	119.3	C17—C16—H16	120.1
C5—C6—H6	119.3	C15—C16—H16	120.1
C6—C7—C8	119.4 (4)	C16—C17—C18	120.3 (4)
C6—C7—H7	120.3	C16—C17—H17	119.9
C8—C7—H7	120.3	C18—C17—H17	119.9
C9—C8—C7	120.9 (5)	C13—C18—C17	119.7 (4)
C9—C8—H8	119.5	C13—C18—H18	120.1
C7—C8—H8	119.5	C17—C18—H18	120.1
C8—C9—C10	122.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.90 (3)	1.99 (2)	2.860 (4)	162 (4)
O1—H1···N1	0.82	1.85	2.574 (4)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.90 (3)	1.99 (2)	2.860 (4)	162 (4)
O1—H1⋯N1	0.82	1.85	2.574 (4)	146

Symmetry code: (i) .