(E)-3-Bromo-N′-(2-hydr­oxy-1-naphthyl­idene)benzohydrazide

Cao, G.-B.; Lu, X.-H.

doi:10.1107/S1600536809022533

organic compounds

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Volume 65| Part 7| July 2009| Page o1600

doi:10.1107/S1600536809022533

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(E)-3-Bromo-N′-(2-hydroxy-1-naphthylidene)benzohydrazide

Guo-Biao Cao ^a ^* and Xu-Hui Lu ^a

^aDepartment of Chemistry, Ankang University, Ankang Shanxi 725000, People's Republic of China
^*Correspondence e-mail: guobiao_cao@126.com

(Received 10 June 2009; accepted 12 June 2009; online 17 June 2009)

The title compound, C₁₈H₁₃BrN₂O₂, was synthesized by the reaction of 2-hydroxy-1-naphthaldehyde with an equimolar quantity of 3-bromobenzohydrazide in methanol. The dihedral angle between the benzene ring and the naphthyl ring system is 18.3 (2)°. An intramolecular O—H⋯N hydrogen bond is observed between the phenolate O and imine N atoms. In the crystal structure, molecules are linked through intermolecular N—H⋯O and C—H⋯O hydrogen bonds, forming a chain running along [101].

Related literature

For crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009 ); Fun et al. (2008 ); Li & Ban (2009 ); Zhu et al. (2009 ); Yang (2007 ); You et al. (2008 ). For hydrazone compounds reported previously by our group, see: Qu et al. (2008 ); Yang et al. (2008 ).

Experimental

Crystal data

C₁₈H₁₃BrN₂O₂
M_r = 369.21
Monoclinic, P 2₁ /n
a = 7.257 (1) Å
b = 31.229 (2) Å
c = 7.327 (1) Å
β = 109.186 (2)°
V = 1568.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.63 mm⁻¹
T = 298 K
0.27 × 0.24 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.505, T_max = 0.548
9563 measured reflections
3393 independent reflections
2177 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.130
S = 1.03
3393 reflections
212 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.95 e Å⁻³
Δρ_min = −0.74 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	1.86	2.584 (4)	146
N2—H2⋯O2ⁱ	0.90 (3)	1.99 (2)	2.840 (4)	159 (4)
C11—H11⋯O2ⁱ	0.92	2.42	3.138 (4)	134
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536809022533/rz2335sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022533/rz2335Isup2.hkl

checkCIF report

Comment top

Study on the crystal structures of hydrazone derivatives is a hot topic in structural chemistry. In the last few years, the crystal structures of a large number of hydrazone compounds have been reported (Mohd Lair et al., 2009; Fun et al., 2008; Li & Ban, 2009; Zhu et al., 2009; Yang, 2007; You et al., 2008). As a continuation of our work in this area (Qu et al., 2008; Yang et al., 2008), the title new hydrazone compound derived from the reaction of 2-hydroxynaphthaldehyde with an equimolar quantity of 3-bromobenzohydrazide is reported.

In the title compound compound (Fig. 1), the dihedral angle between the benzene ring system and the naphthyl ring is 18.3 (2)°. An intramolecular O—H···N hydrogen bond is observed between the phenolate O and imine N atoms. In the crystal structure, molecules are linked through intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) to form a chain running along [101] (Fig. 2).

Related literature top

For examples of crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009); Fun et al. (2008); Li & Ban (2009); Zhu et al. (2009); Yang (2007); You et al. (2008). For hydrazone compounds reported previously by our group, see: Qu et al. (2008); Yang et al. (2008).

Experimental top

The title compound was prepared by refluxing equimolar quantities of 2-hydroxynaphthaldehyde with 3-bromobenzohydrazide in methanol. Colourless block-like crystals were formed by slow evaporation of the solution in air.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 displacement ellipsoids drawn at the 30% probability level. The intermolecular O—H···N hydrogen bond is shown as a dashed line.
	Fig. 2. The molecular packing of the title compound, viewed along the c axis. Hydrogen bonds are drawn as dashed lines.

(E)-3-Bromo-N'-(2-hydroxy-1-naphthylidene)benzohydrazide top

Crystal data top

C₁₈H₁₃BrN₂O₂	F(000) = 744
M_r = 369.21	D_x = 1.564 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2089 reflections
a = 7.257 (1) Å	θ = 2.5–24.1°
b = 31.229 (2) Å	µ = 2.63 mm⁻¹
c = 7.327 (1) Å	T = 298 K
β = 109.186 (2)°	Block, colourless
V = 1568.3 (3) Å³	0.27 × 0.24 × 0.23 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3393 independent reflections
Radiation source: fine-focus sealed tube	2177 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 27.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.505, T_max = 0.548	k = −33→39
9563 measured reflections	l = −9→9

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0521P)² + 1.3512P] where P = (F_o² + 2F_c²)/3
3393 reflections	(Δ/σ)_max = 0.001
212 parameters	Δρ_max = 0.95 e Å⁻³
1 restraint	Δρ_min = −0.74 e Å⁻³

Crystal data top

C₁₈H₁₃BrN₂O₂	V = 1568.3 (3) Å³
M_r = 369.21	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.257 (1) Å	µ = 2.63 mm⁻¹
b = 31.229 (2) Å	T = 298 K
c = 7.327 (1) Å	0.27 × 0.24 × 0.23 mm
β = 109.186 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3393 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2177 reflections with I > 2σ(I)
T_min = 0.505, T_max = 0.548	R_int = 0.042
9563 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	1 restraint
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.95 e Å⁻³
3393 reflections	Δρ_min = −0.74 e Å⁻³
212 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	0.65464 (7)	0.056963 (13)	0.64773 (9)	0.0777 (2)
N1	0.5623 (4)	0.28551 (9)	0.3163 (4)	0.0421 (7)
N2	0.5913 (4)	0.25667 (9)	0.4663 (4)	0.0422 (7)
O1	0.4950 (4)	0.30515 (9)	−0.0423 (4)	0.0582 (7)
H1	0.5018	0.2894	0.0491	0.087*
O2	0.4065 (4)	0.20685 (8)	0.2666 (3)	0.0519 (7)
C1	0.6106 (5)	0.35584 (11)	0.2181 (5)	0.0370 (8)
C2	0.5493 (5)	0.34517 (12)	0.0233 (5)	0.0431 (8)
C3	0.5414 (6)	0.37649 (14)	−0.1167 (5)	0.0548 (10)
H3	0.5041	0.3687	−0.2463	0.066*
C4	0.5868 (6)	0.41757 (14)	−0.0669 (6)	0.0564 (11)
H4	0.5789	0.4377	−0.1628	0.068*
C5	0.6461 (5)	0.43074 (12)	0.1279 (5)	0.0460 (9)
C6	0.6938 (6)	0.47395 (13)	0.1836 (7)	0.0596 (11)
H6	0.6865	0.4943	0.0889	0.072*
C7	0.7495 (7)	0.48622 (14)	0.3699 (8)	0.0687 (13)
H7	0.7765	0.5149	0.4026	0.082*
C8	0.7662 (7)	0.45580 (14)	0.5133 (7)	0.0664 (12)
H8	0.8070	0.4643	0.6422	0.080*
C9	0.7234 (6)	0.41362 (12)	0.4677 (6)	0.0536 (10)
H9	0.7361	0.3939	0.5662	0.064*
C10	0.6602 (5)	0.39952 (11)	0.2733 (5)	0.0389 (8)
C11	0.6256 (5)	0.32334 (11)	0.3624 (5)	0.0391 (8)
H11	0.6829	0.3302	0.4923	0.047*
C12	0.5114 (5)	0.21769 (11)	0.4285 (5)	0.0377 (8)
C13	0.5620 (5)	0.18763 (11)	0.5957 (5)	0.0380 (8)
C14	0.5772 (5)	0.14454 (11)	0.5566 (5)	0.0414 (8)
H14	0.5539	0.1355	0.4300	0.050*
C15	0.6263 (5)	0.11530 (12)	0.7037 (6)	0.0468 (9)
C16	0.6536 (6)	0.12784 (14)	0.8898 (6)	0.0589 (11)
H16	0.6840	0.1077	0.9886	0.071*
C17	0.6359 (6)	0.17036 (15)	0.9303 (6)	0.0599 (11)
H17	0.6546	0.1789	1.0567	0.072*
C18	0.5903 (5)	0.20061 (12)	0.7827 (5)	0.0466 (9)
H18	0.5790	0.2294	0.8101	0.056*
H2	0.682 (5)	0.2631 (14)	0.580 (4)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0680 (3)	0.0401 (3)	0.1356 (5)	0.0096 (2)	0.0481 (3)	0.0197 (3)
N1	0.0472 (18)	0.0343 (15)	0.0368 (16)	0.0008 (13)	0.0029 (13)	0.0047 (13)
N2	0.0506 (19)	0.0339 (15)	0.0331 (15)	−0.0033 (13)	0.0015 (13)	0.0031 (13)
O1	0.075 (2)	0.0555 (17)	0.0404 (15)	−0.0080 (15)	0.0144 (14)	−0.0071 (13)
O2	0.0624 (18)	0.0407 (14)	0.0370 (14)	−0.0040 (12)	−0.0048 (12)	−0.0023 (11)
C1	0.0329 (18)	0.0374 (18)	0.0396 (19)	0.0012 (14)	0.0102 (14)	0.0042 (15)
C2	0.039 (2)	0.048 (2)	0.042 (2)	0.0022 (16)	0.0129 (16)	0.0051 (17)
C3	0.060 (3)	0.069 (3)	0.035 (2)	0.002 (2)	0.0138 (18)	0.0068 (19)
C4	0.057 (3)	0.061 (3)	0.055 (3)	0.011 (2)	0.023 (2)	0.025 (2)
C5	0.039 (2)	0.045 (2)	0.056 (2)	0.0066 (16)	0.0200 (17)	0.0120 (18)
C6	0.054 (3)	0.043 (2)	0.090 (3)	0.0031 (19)	0.034 (2)	0.020 (2)
C7	0.075 (3)	0.038 (2)	0.100 (4)	−0.008 (2)	0.039 (3)	−0.004 (2)
C8	0.074 (3)	0.054 (3)	0.073 (3)	−0.013 (2)	0.027 (2)	−0.012 (2)
C9	0.066 (3)	0.042 (2)	0.054 (2)	−0.0050 (19)	0.022 (2)	−0.0023 (18)
C10	0.0304 (18)	0.0401 (18)	0.047 (2)	0.0021 (14)	0.0135 (15)	0.0042 (16)
C11	0.039 (2)	0.0365 (19)	0.0364 (18)	0.0031 (15)	0.0057 (15)	0.0020 (15)
C12	0.0345 (19)	0.0372 (18)	0.0370 (19)	0.0027 (14)	0.0059 (15)	−0.0028 (15)
C13	0.0315 (18)	0.0393 (19)	0.0391 (19)	−0.0002 (15)	0.0061 (14)	0.0039 (15)
C14	0.0347 (19)	0.0401 (19)	0.048 (2)	−0.0020 (15)	0.0123 (16)	0.0012 (17)
C15	0.035 (2)	0.043 (2)	0.064 (3)	0.0002 (16)	0.0188 (18)	0.0123 (18)
C16	0.049 (3)	0.067 (3)	0.060 (3)	0.001 (2)	0.016 (2)	0.026 (2)
C17	0.057 (3)	0.082 (3)	0.038 (2)	−0.004 (2)	0.0129 (18)	0.009 (2)
C18	0.048 (2)	0.048 (2)	0.042 (2)	−0.0047 (17)	0.0140 (17)	−0.0012 (17)

Geometric parameters (Å, º) top

Br1—C15	1.894 (4)	C6—H6	0.9300
N1—C11	1.272 (4)	C7—C8	1.392 (6)
N1—N2	1.383 (4)	C7—H7	0.9300
N2—C12	1.338 (4)	C8—C9	1.369 (6)
N2—H2	0.90 (3)	C8—H8	0.9300
O1—C2	1.350 (4)	C9—C10	1.415 (5)
O1—H1	0.8200	C9—H9	0.9300
O2—C12	1.227 (4)	C11—H11	0.9300
C1—C2	1.389 (5)	C12—C13	1.490 (5)
C1—C10	1.435 (5)	C13—C18	1.378 (5)
C1—C11	1.444 (5)	C13—C14	1.388 (5)
C2—C3	1.405 (5)	C14—C15	1.368 (5)
C3—C4	1.345 (6)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.369 (6)
C4—C5	1.410 (6)	C16—C17	1.375 (6)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.419 (6)	C17—C18	1.391 (5)
C5—C10	1.423 (5)	C17—H17	0.9300
C6—C7	1.346 (6)	C18—H18	0.9300

C11—N1—N2	116.5 (3)	C8—C9—H9	119.4
C12—N2—N1	119.1 (3)	C10—C9—H9	119.4
C12—N2—H2	122 (3)	C9—C10—C5	117.4 (3)
N1—N2—H2	118 (3)	C9—C10—C1	123.2 (3)
C2—O1—H1	109.5	C5—C10—C1	119.4 (3)
C2—C1—C10	118.9 (3)	N1—C11—C1	121.7 (3)
C2—C1—C11	120.4 (3)	N1—C11—H11	119.2
C10—C1—C11	120.7 (3)	C1—C11—H11	119.2
O1—C2—C1	123.0 (3)	O2—C12—N2	122.7 (3)
O1—C2—C3	116.6 (3)	O2—C12—C13	121.8 (3)
C1—C2—C3	120.4 (3)	N2—C12—C13	115.5 (3)
C4—C3—C2	121.2 (4)	C18—C13—C14	119.6 (3)
C4—C3—H3	119.4	C18—C13—C12	123.2 (3)
C2—C3—H3	119.4	C14—C13—C12	117.1 (3)
C3—C4—C5	121.3 (4)	C15—C14—C13	120.2 (4)
C3—C4—H4	119.4	C15—C14—H14	119.9
C5—C4—H4	119.4	C13—C14—H14	119.9
C4—C5—C6	122.2 (4)	C14—C15—C16	120.6 (4)
C4—C5—C10	118.7 (4)	C14—C15—Br1	119.4 (3)
C6—C5—C10	119.1 (4)	C16—C15—Br1	120.0 (3)
C7—C6—C5	121.7 (4)	C15—C16—C17	119.8 (4)
C7—C6—H6	119.1	C15—C16—H16	120.1
C5—C6—H6	119.1	C17—C16—H16	120.1
C6—C7—C8	119.6 (4)	C16—C17—C18	120.2 (4)
C6—C7—H7	120.2	C16—C17—H17	119.9
C8—C7—H7	120.2	C18—C17—H17	119.9
C9—C8—C7	121.0 (4)	C13—C18—C17	119.5 (4)
C9—C8—H8	119.5	C13—C18—H18	120.2
C7—C8—H8	119.5	C17—C18—H18	120.2
C8—C9—C10	121.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.584 (4)	146
N2—H2···O2ⁱ	0.90 (3)	1.99 (2)	2.840 (4)	159 (4)
C11—H11···O2ⁱ	0.92	2.42	3.138 (4)	134

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃BrN₂O₂
M_r	369.21
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.257 (1), 31.229 (2), 7.327 (1)
β (°)	109.186 (2)
V (Å³)	1568.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.63
Crystal size (mm)	0.27 × 0.24 × 0.23

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.505, 0.548
No. of measured, independent and observed [I > 2σ(I)] reflections	9563, 3393, 2177
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.130, 1.03
No. of reflections	3393
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)	0.95, −0.74

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.584 (4)	145.8
N2—H2···O2ⁱ	0.90 (3)	1.99 (2)	2.840 (4)	159 (4)
C11—H11···O2ⁱ	0.92	2.42	3.138 (4)	134

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

Acknowledgements

The Vital Foundation of Ankang University (project No. 2008AKXY012) and the Special Scientific Research Foundation of the Education Office of Shanxi Province (Project No. 02JK202) are gratefully acknowledged.

References

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