(E)-3-Bromo-N'-(2-hydr-oxy-1-naphthyl-idene)benzohydrazide.

The title compound, C(18)H(13)BrN(2)O(2), was synthesized by the reaction of 2-hydr-oxy-1-naphthaldehyde with an equimolar quantity of 3-bromo-benzohydrazide in methanol. The dihedral angle between the benzene ring and the naphthyl ring system is 18.3 (2)°. An intra-molecular O-H⋯N hydrogen bond is observed between the phenolate O and imine N atoms. In the crystal structure, mol-ecules are linked through inter-molecular 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 = 369.21

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.130

S = 1.03

3393 reflections

212 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.95 e Å−3

Δρmin = −0.74 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022533/rz2335sup1.cif

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

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

C18H13BrN2O2	F(000) = 744
Mr = 369.21	Dx = 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

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

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(Fo2) + (0.0521P)2 + 1.3512P] where P = (Fo2 + 2Fc2)/3
3393 reflections	(Δ/σ)max = 0.001
212 parameters	Δρmax = 0.95 e Å−3
1 restraint	Δρmin = −0.74 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .