(E)-4-Bromo-N'-(2-hydr-oxy-1-naphthyl-methyl-ene)benzohydrazide.

The title compound, C(18)H(13)BrN(2)O(2), was synthesized by the reaction of 2-hydr-oxy-1-naphthaldehyde with 4-bromo-benzohydrazide. This Schiff base mol-ecule 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 intra-molecular O-H⋯N hydrogen bond involving the naphthyl hydr-oxy substituent and the N' atom of the hydrazide group. In the crystal structure, mol-ecules are linked through inter-molecular 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 = 369.21

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.101

S = 0.90

3119 reflections

212 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1493 Friedel pairs

Flack parameter: 0.026 (12)

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031395/su2066sup1.cif

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

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

C18H13BrN2O2	F(000) = 372
Mr = 369.21	Dx = 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

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

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(Fo2) + ]
S = 0.90	(Δ/σ)max = 0.001
3119 reflections	Δρmax = 0.31 e Å−3
212 parameters	Δρmin = −0.24 e Å−3
3 restraints	Absolute structure: Flack (1983), 1493 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.026 (12)

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
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*

	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)

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)

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

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) .