3-Chloro-N′-[(2-hy­droxy­naphthalen-1-yl)methyl­idene]benzohydrazide

Li, T.-Y.; Li, W.

doi:10.1107/S1600536811000912

organic compounds

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Volume 67| Part 2| February 2011| Page o373

doi:10.1107/S1600536811000912

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3-Chloro-N′-[(2-hydroxynaphthalen-1-yl)methylidene]benzohydrazide

Tian-Yi Li ^a ^* and Wei Li ^a

^aSchool of Chemical Engineering, Changchun University of Technology, Changchun 130012, People's Republic of China
^*Correspondence e-mail: cooperationwell@126.com

(Received 31 December 2010; accepted 6 January 2011; online 12 January 2011)

The title compound, C₁₈H₁₃ClN₂O₂, was prepared by the reaction of 2-hydroxy-1-naphthaldehyde with 3-chlorobenzohydrazide in methanol. An intramolecular O—H⋯N hydrogen bond influences the molecular conformation; the benzene ring and naphthyl ring system form a dihedral angle of 17.1 (3)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules 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_r = 324.75
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.082
wR(F²) = 0.161
S = 1.04
3288 reflections
212 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.35 e Å⁻³

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) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

In the last years, a number of Schiff bases derived from the reaction of aldehydes with benzohydrazides were prepared and structurally characterized (Bessy et al., 2006; Podyachev et al., 2007; Raj & Kurup, 2007; Pouralimardan et al., 2007; Bacchi et al., 2006; Dinda et al., 2002). As a contribution to this work, we present here the title new Schiff base compound (Fig. 1).

There is an intramolecular O—H···N hydrogen bond in the molecule, which influences the molecular conformation - the dihedral angle between the benzene ring and the naphthyl ring is 17.1 (3)°. All the bond lengths are within normal values (Allen et al., 1987). In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains propagated in [101] (Fig. 2).

Related literature top

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 top

The compound was prepared and crystallized according to the literature method (Zhu, 2010). 2-Hydroxy-1-naphthaldehyde (0.172 g, 1 mmol) and 3-chlorobenzohydrazide (0.171 g, 1 mmol) were dissolved in 30 ml absolute methanol. The mixture was stirred at reflux for 10 min, and cooled to room temperature. The clear colorless solution was left to slow evaporation in air for five days, yielding colorless block-shaped crystals, which were collected by filtration and washed with methanol.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids for non-hydrogen atoms. Intramolecular O—H···N hydrogen bond is drawn as a dashed line.
	Fig. 2. A portion of the crystal packing showing H-bonds as dashed lines.

3-Chloro-N'-[(2-hydroxynaphthalen-1-yl)methylidene]benzohydrazide top

Crystal data top

C₁₈H₁₃ClN₂O₂	F(000) = 672
M_r = 324.75	D_x = 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

Data collection top

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

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)] = 0.082	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(F_o²) + (0.0443P)² + 0.9339P] where P = (F_o² + 2F_c²)/3
3288 reflections	(Δ/σ)_max < 0.001
212 parameters	Δρ_max = 0.24 e Å⁻³
1 restraint	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₈H₁₃ClN₂O₂	V = 1541.9 (5) Å³
M_r = 324.75	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.158 (2) Å	µ = 0.26 mm⁻¹
b = 30.886 (3) Å	T = 298 K
c = 7.3733 (12) Å	0.20 × 0.20 × 0.18 mm
β = 108.924 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3288 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1635 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.955	R_int = 0.062
8306 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	1 restraint
wR(F²) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.24 e Å⁻³
3288 reflections	Δρ_min = −0.35 e Å⁻³
212 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	0.66632 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃ClN₂O₂
M_r	324.75
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.158 (2), 30.886 (3), 7.3733 (12)
β (°)	108.924 (2)
V (Å³)	1541.9 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.950, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	8306, 3288, 1635
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.161, 1.04
No. of reflections	3288
No. of parameters	212
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)	0.24, −0.35

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.90 (3)	1.992 (17)	2.860 (4)	162 (4)
O1—H1···N1	0.82	1.85	2.574 (4)	146

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

References

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doi:10.1107/S1600536811000912

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