(E)-4-Bromo-N′-(2-hydr­oxy-1-naphthyl­methyl­ene)benzohydrazide

Diao, Y.-P.; Zhang, Q.-H.; Wang, D.-C.; Deng, X.-M.

doi:10.1107/S1600536808031395

organic compounds

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Volume 64| Part 11| November 2008| Page o2070

doi:10.1107/S1600536808031395

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(E)-4-Bromo-N′-(2-hydroxy-1-naphthylmethylene)benzohydrazide

Yun-Peng Diao,^a,^b Qi-Hui Zhang,^c Da-Cheng Wang ^a and Xu-Ming Deng ^a ^*

^aCollege of Animal Science and Veterinary Medicine, Jilin University, Jilin 130062, People's Republic of China, ^bCollege of Pharmacy, Dalian Medical University, Dalian 116044, People's Republic of China, and ^cSchool of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China
^*Correspondence e-mail: xumingdeng08@126.com

(Received 21 September 2008; accepted 28 September 2008; online 4 October 2008)

The title compound, C₁₈H₁₃BrN₂O₂, was synthesized by the reaction of 2-hydroxy-1-naphthaldehyde with 4-bromobenzohydrazide. This Schiff base molecule has an E configuration about the C=N bond and is almost planar, the dihedral angle between the mean planes through the substituted benzene ring and the naphthyl system being 6.6 (2)°. There is an intramolecular O—H⋯N hydrogen bond involving the naphthyl hydroxy substituent and the N′ atom of the hydrazide group. In the crystal structure, molecules are linked through intermolecular N—-H⋯O hydrogen bonds to form chains extending along the b direction.

Related literature

For related structures, see: Brückner et al. (2000 ); Diao (2007 ); Diao et al. (2007 , 2008 ); Harrop et al. (2003 ); Huang et al. (2007 ); Li et al. (2007 ); Ren et al. (2002 ).

Experimental

Crystal data

C₁₈H₁₃BrN₂O₂
M_r = 369.21
Monoclinic, P c
a = 6.185 (2) Å
b = 4.7638 (19) Å
c = 25.689 (10) Å
β = 95.449 (7)°
V = 753.5 (5) Å³
Z = 2
Mo Kα radiation
μ = 2.74 mm⁻¹
T = 298 (2) K
0.30 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.494, T_max = 0.514 (expected range = 0.446–0.464)
5817 measured reflections
3119 independent reflections
2443 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.101
S = 0.90
3119 reflections
212 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 1493 Friedel pairs
Flack parameter: 0.026 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.89 (3)	1.99 (3)	2.841 (4)	160 (6)
O2—H2⋯N2	0.82	1.86	2.580 (4)	145
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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/S1600536808031395/su2066sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031395/su2066Isup2.hkl

checkCIF report

Comment top

Schiff base compounds have been found to have potential pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). Recently, a few Schiff base compounds obtained from the reaction of aldehydes with benzohydrazides have been reported (Diao et al., 2008; Diao et al., 2007; Diao, 2007; Li et al., 2007; Huang et al., 2007). As a further study of such compounds, we report here on the structure of the title compound.

The title compound, a Schiff base synthesized by the reaction of 2-hydroxy-1-naphthaldehyde with 4-bromobenzohydrazide, is almost planar (Fig. 1), with the dihedral angle between the mean planes of the substituted benzene ring and the naphthyl ring being only 6.6 (2)°. The torsion angles C4—C6—N1—N2 and C8—C7—N2—N1 are 0.9 (3) and 2.9 (3)°, respectively. There is an intramolecular O-H···N hydrogen bond involving the naphthyl hydroxyl substituent and the NH H-atom of the hydrazide group (Table 1).

In the crystal molecules are linked via N–H···O intermolecular hydrogen bonds (Table 1), to form chains extending in the b direction (Fig. 2).

Related literature top

For related structures, see: Brückner et al. (2000); Diao (2007); Diao et al. (2007, 2008); Harrop et al. (2003); Huang et al. (2007); Li et al. (2007); Ren et al. (2002).

Experimental top

4-Bromobenzaldehyde (0.1 mmol, 18.5 mg) and 2-hydroxy-1-naphthaldehyde (0.1 mmol, 17.2 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 1 h and cooled to room temperature. After keeping the solution in air for alomost two weeks, yellow block-like crystals of the title compound were formed.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 parameters drawn at the 30% probability level.
	Fig. 2. A persepctive view along the a axis of the crystal packing of the title compound.

(E)-4-Bromo-N'-(2-hydroxy-1-naphthylmethylene)benzohydrazide top

Crystal data top

C₁₈H₁₃BrN₂O₂	F(000) = 372
M_r = 369.21	D_x = 1.627 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
a = 6.185 (2) Å	Cell parameters from 1589 reflections
b = 4.7638 (19) Å	θ = 2.6–24.5°
c = 25.689 (10) Å	µ = 2.74 mm⁻¹
β = 95.449 (7)°	T = 298 K
V = 753.5 (5) Å³	Block, yellow
Z = 2	0.30 × 0.30 × 0.28 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3119 independent reflections
Radiation source: fine-focus sealed tube	2443 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 27.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→7
T_min = 0.494, T_max = 0.514	k = −6→6
5817 measured reflections	l = −32→32

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.101	w = 1/[σ²(F_o²) + ]
S = 0.90	(Δ/σ)_max = 0.001
3119 reflections	Δρ_max = 0.31 e Å⁻³
212 parameters	Δρ_min = −0.24 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 1493 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.026 (12)

Crystal data top

C₁₈H₁₃BrN₂O₂	V = 753.5 (5) Å³
M_r = 369.21	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 6.185 (2) Å	µ = 2.74 mm⁻¹
b = 4.7638 (19) Å	T = 298 K
c = 25.689 (10) Å	0.30 × 0.30 × 0.28 mm
β = 95.449 (7)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3119 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2443 reflections with I > 2σ(I)
T_min = 0.494, T_max = 0.514	R_int = 0.034
5817 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.101	Δρ_max = 0.31 e Å⁻³
S = 0.90	Δρ_min = −0.24 e Å⁻³
3119 reflections	Absolute structure: Flack (1983), 1493 Friedel pairs
212 parameters	Absolute structure parameter: 0.026 (12)
3 restraints

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
Br1	1.08310 (11)	0.22527 (11)	1.13545 (4)	0.0685 (2)
O1	0.2012 (5)	−0.3701 (5)	0.99811 (12)	0.0474 (7)
O2	−0.3678 (6)	−0.2844 (6)	0.91908 (13)	0.0509 (8)
H2	−0.2458	−0.2481	0.9327	0.076*
N1	0.1759 (5)	0.0647 (6)	0.96274 (13)	0.0379 (7)
N2	−0.0057 (5)	−0.0129 (6)	0.93167 (12)	0.0377 (7)
C18	0.7851 (7)	0.2520 (7)	1.04481 (17)	0.0407 (9)
H18	0.8775	0.3902	1.0342	0.049*
C1	0.8295 (7)	0.1191 (9)	1.09188 (16)	0.0433 (9)
C2	0.6996 (7)	−0.0854 (9)	1.10869 (16)	0.0480 (10)
H2A	0.7329	−0.1711	1.1410	0.058*
C3	0.5173 (7)	−0.1632 (8)	1.07685 (17)	0.0432 (10)
H3	0.4282	−0.3052	1.0875	0.052*
C4	0.4659 (6)	−0.0328 (7)	1.02954 (15)	0.0340 (8)
C5	0.6012 (6)	0.1770 (7)	1.01362 (16)	0.0369 (8)
H5	0.5673	0.2669	0.9818	0.044*
C6	0.2705 (6)	−0.1305 (8)	0.99609 (15)	0.0350 (8)
C7	−0.0776 (6)	0.1545 (8)	0.89501 (16)	0.0357 (8)
H7	−0.0023	0.3190	0.8893	0.043*
C8	−0.2727 (6)	0.0903 (7)	0.86278 (15)	0.0361 (8)
C9	−0.4138 (6)	−0.1175 (8)	0.87700 (16)	0.0399 (9)
C10	−0.6139 (7)	−0.1627 (9)	0.8477 (2)	0.0513 (11)
H10	−0.7084	−0.2975	0.8587	0.062*
C11	−0.6716 (6)	−0.0146 (9)	0.80394 (19)	0.0527 (11)
H11	−0.8065	−0.0462	0.7857	0.063*
C12	−0.5319 (7)	0.1866 (8)	0.78536 (19)	0.0459 (10)
C13	−0.5851 (8)	0.3322 (10)	0.7382 (2)	0.0558 (12)
H13	−0.7177	0.2963	0.7191	0.067*
C14	−0.4491 (8)	0.5229 (10)	0.71980 (18)	0.0596 (12)
H14	−0.4861	0.6156	0.6883	0.071*
C15	−0.2513 (8)	0.5774 (10)	0.74925 (17)	0.0568 (11)
H15	−0.1576	0.7101	0.7372	0.068*
C16	−0.1927 (6)	0.4422 (8)	0.79472 (15)	0.0441 (9)
H16	−0.0587	0.4806	0.8129	0.053*
C17	−0.3314 (6)	0.2444 (7)	0.81494 (17)	0.0377 (9)
H1	0.209 (11)	0.245 (4)	0.969 (3)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0451 (2)	0.0994 (4)	0.0583 (3)	−0.0070 (3)	−0.00903 (17)	−0.0151 (3)
O1	0.0489 (17)	0.0246 (13)	0.068 (2)	−0.0093 (12)	−0.0010 (14)	0.0020 (13)
O2	0.055 (2)	0.0432 (16)	0.055 (2)	−0.0164 (13)	0.0070 (15)	−0.0067 (14)
N1	0.0431 (18)	0.0268 (15)	0.0425 (18)	−0.0060 (14)	−0.0022 (14)	−0.0048 (13)
N2	0.0343 (15)	0.0308 (15)	0.0473 (19)	−0.0038 (13)	0.0002 (13)	−0.0074 (14)
C18	0.036 (2)	0.043 (2)	0.044 (2)	−0.0092 (17)	0.0070 (17)	−0.0058 (17)
C1	0.036 (2)	0.047 (2)	0.046 (3)	−0.0004 (18)	0.0002 (17)	−0.0128 (19)
C2	0.050 (2)	0.050 (3)	0.042 (2)	0.000 (2)	−0.0038 (19)	0.0053 (19)
C3	0.044 (2)	0.035 (2)	0.051 (3)	−0.0049 (17)	0.0040 (19)	0.0034 (17)
C4	0.038 (2)	0.0274 (18)	0.037 (2)	−0.0041 (15)	0.0040 (15)	−0.0030 (15)
C5	0.038 (2)	0.0343 (19)	0.038 (2)	−0.0062 (15)	0.0045 (16)	−0.0027 (15)
C6	0.038 (2)	0.0250 (18)	0.043 (2)	−0.0006 (16)	0.0105 (17)	−0.0058 (16)
C7	0.035 (2)	0.0306 (18)	0.041 (2)	−0.0062 (15)	0.0040 (16)	−0.0041 (16)
C8	0.036 (2)	0.0308 (18)	0.041 (2)	−0.0011 (16)	0.0023 (16)	−0.0111 (16)
C9	0.041 (2)	0.035 (2)	0.044 (2)	−0.0055 (17)	0.0084 (17)	−0.0101 (17)
C10	0.038 (2)	0.049 (2)	0.068 (3)	−0.0138 (19)	0.008 (2)	−0.015 (2)
C11	0.031 (2)	0.060 (3)	0.064 (3)	−0.0061 (18)	−0.0082 (18)	−0.023 (2)
C12	0.038 (2)	0.044 (2)	0.055 (3)	0.0017 (17)	−0.0037 (19)	−0.0178 (18)
C13	0.049 (3)	0.057 (3)	0.057 (3)	0.009 (2)	−0.013 (2)	−0.015 (2)
C14	0.067 (3)	0.068 (3)	0.043 (3)	0.010 (3)	−0.003 (2)	−0.001 (2)
C15	0.059 (3)	0.066 (3)	0.046 (3)	−0.002 (2)	0.008 (2)	−0.001 (2)
C16	0.038 (2)	0.051 (3)	0.044 (2)	−0.0058 (18)	0.0023 (17)	−0.0005 (19)
C17	0.033 (2)	0.036 (2)	0.043 (2)	0.0018 (15)	0.0005 (16)	−0.0104 (16)

Geometric parameters (Å, º) top

Br1—C1	1.907 (4)	C7—C8	1.430 (5)
O1—C6	1.222 (5)	C7—H7	0.9300
O2—C9	1.350 (5)	C8—C9	1.391 (5)
O2—H2	0.8200	C8—C17	1.448 (6)
N1—C6	1.359 (5)	C9—C10	1.403 (6)
N1—N2	1.366 (4)	C10—C11	1.346 (7)
N1—H1	0.89 (3)	C10—H10	0.9300
N2—C7	1.281 (5)	C11—C12	1.404 (6)
C18—C1	1.369 (6)	C11—H11	0.9300
C18—C5	1.375 (6)	C12—C13	1.407 (7)
C18—H18	0.9300	C12—C17	1.419 (6)
C1—C2	1.359 (6)	C13—C14	1.354 (7)
C2—C3	1.379 (6)	C13—H13	0.9300
C2—H2A	0.9300	C14—C15	1.400 (7)
C3—C4	1.375 (5)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.353 (6)
C4—C5	1.389 (5)	C15—H15	0.9300
C4—C6	1.490 (5)	C16—C17	1.406 (6)
C5—H5	0.9300	C16—H16	0.9300

C9—O2—H2	109.5	C9—C8—C17	118.1 (3)
C6—N1—N2	117.7 (3)	C7—C8—C17	120.8 (3)
C6—N1—H1	118 (5)	O2—C9—C8	122.7 (4)
N2—N1—H1	121 (5)	O2—C9—C10	116.6 (4)
C7—N2—N1	118.0 (3)	C8—C9—C10	120.8 (4)
C1—C18—C5	118.7 (4)	C11—C10—C9	121.2 (4)
C1—C18—H18	120.7	C11—C10—H10	119.4
C5—C18—H18	120.7	C9—C10—H10	119.4
C2—C1—C18	122.5 (4)	C10—C11—C12	121.3 (4)
C2—C1—Br1	118.8 (3)	C10—C11—H11	119.4
C18—C1—Br1	118.7 (3)	C12—C11—H11	119.4
C1—C2—C3	118.6 (4)	C11—C12—C13	121.9 (4)
C1—C2—H2A	120.7	C11—C12—C17	119.0 (4)
C3—C2—H2A	120.7	C13—C12—C17	119.1 (4)
C4—C3—C2	120.7 (4)	C14—C13—C12	121.9 (4)
C4—C3—H3	119.7	C14—C13—H13	119.0
C2—C3—H3	119.7	C12—C13—H13	119.0
C3—C4—C5	119.3 (4)	C13—C14—C15	118.4 (4)
C3—C4—C6	118.4 (3)	C13—C14—H14	120.8
C5—C4—C6	122.2 (4)	C15—C14—H14	120.8
C18—C5—C4	120.2 (4)	C16—C15—C14	121.8 (5)
C18—C5—H5	119.9	C16—C15—H15	119.1
C4—C5—H5	119.9	C14—C15—H15	119.1
O1—C6—N1	122.3 (3)	C15—C16—C17	121.0 (4)
O1—C6—C4	122.4 (3)	C15—C16—H16	119.5
N1—C6—C4	115.3 (3)	C17—C16—H16	119.5
N2—C7—C8	120.5 (3)	C16—C17—C12	117.7 (4)
N2—C7—H7	119.8	C16—C17—C8	122.7 (4)
C8—C7—H7	119.8	C12—C17—C8	119.5 (4)
C9—C8—C7	121.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.89 (3)	1.99 (3)	2.841 (4)	160 (6)
O2—H2···N2	0.82	1.86	2.580 (4)	145

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃BrN₂O₂
M_r	369.21
Crystal system, space group	Monoclinic, Pc
Temperature (K)	298
a, b, c (Å)	6.185 (2), 4.7638 (19), 25.689 (10)
β (°)	95.449 (7)
V (Å³)	753.5 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.74
Crystal size (mm)	0.30 × 0.30 × 0.28

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.494, 0.514
No. of measured, independent and observed [I > 2σ(I)] reflections	5817, 3119, 2443
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.101, 0.90
No. of reflections	3119
No. of parameters	212
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.24
Absolute structure	Flack (1983), 1493 Friedel pairs
Absolute structure parameter	0.026 (12)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.89 (3)	1.99 (3)	2.841 (4)	160 (6)
O2—H2···N2	0.82	1.86	2.580 (4)	145.4

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

References

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doi:10.1107/S1600536808031395

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