3-Bromo-N'-[(2-meth-oxy-naphthalen-1-yl)methyl-idene]benzohydrazide.

The mol-ecule of the title compound, C(19)H(15)BrN(2)O(2), displays a pseudo-trans conformation about the N-N bond [C-N-N=C torsion angle = 164.7 (2)°]. The dihedral angle between the planes of the benzene ring and the naphthyl system is 70.1 (2)°. In the crystal, mol-ecules are linked into C(4) chains along the c axis by N-H⋯O hydrogen bonds.

Related literature

For related structures, see: Li (2007a ▶,b ▶, 2008 ▶); Qiu et al. (2006 ▶); Yang & Guo (2006 ▶); Yang (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H15BrN2O2

M = 383.24

Monoclinic,

a = 12.3562 (11) Å

b = 17.0404 (15) Å

c = 8.6175 (10) Å

β = 110.155 (2)°

V = 1703.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.43 mm−1

T = 298 K

0.30 × 0.27 × 0.27 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.530, T max = 0.560

9533 measured reflections

3513 independent reflections

1721 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.132

S = 1.00

3513 reflections

221 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811019349/hb5889sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019349/hb5889Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019349/hb5889Isup3.cml

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

C19H15BrN2O2	F(000) = 776
Mr = 383.24	Dx = 1.494 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1085 reflections
a = 12.3562 (11) Å	θ = 2.3–24.5°
b = 17.0404 (15) Å	µ = 2.43 mm−1
c = 8.6175 (10) Å	T = 298 K
β = 110.155 (2)°	Block, colorless
V = 1703.3 (3) Å3	0.30 × 0.27 × 0.27 mm
Z = 4

Bruker SMART CCD diffractometer	3513 independent reflections
Radiation source: fine-focus sealed tube	1721 reflections with I > 2σ(I)
graphite	Rint = 0.080
ω scans	θmax = 26.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→15
Tmin = 0.530, Tmax = 0.560	k = −21→18
9533 measured reflections	l = −10→10

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3
3513 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.30 e Å−3
1 restraint	Δρmin = −0.36 e Å−3

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	0.92086 (5)	0.10384 (4)	0.45503 (6)	0.0640 (3)
N1	0.6290 (3)	0.2794 (2)	0.8906 (4)	0.0378 (10)
N2	0.7166 (3)	0.2434 (2)	0.8493 (4)	0.0389 (10)
O1	0.5703 (3)	0.4903 (2)	0.7240 (4)	0.0668 (11)
O2	0.7770 (3)	0.17262 (19)	1.0857 (4)	0.0534 (9)
C1	0.4904 (4)	0.3853 (3)	0.8237 (5)	0.0394 (12)
C2	0.4835 (5)	0.4634 (3)	0.7754 (6)	0.0500 (14)
C3	0.3937 (6)	0.5126 (3)	0.7840 (7)	0.0658 (17)
H3	0.3901	0.5649	0.7519	0.079*
C4	0.3128 (5)	0.4821 (4)	0.8402 (7)	0.0679 (17)
H4	0.2538	0.5145	0.8460	0.082*
C5	0.3145 (4)	0.4033 (3)	0.8900 (6)	0.0481 (13)
C6	0.2266 (5)	0.3738 (4)	0.9432 (7)	0.0690 (17)
H6	0.1677	0.4069	0.9472	0.083*
C7	0.2270 (5)	0.2978 (4)	0.9885 (7)	0.0715 (18)
H7	0.1683	0.2786	1.0223	0.086*
C8	0.3164 (5)	0.2483 (3)	0.9841 (7)	0.0618 (15)
H8	0.3172	0.1963	1.0170	0.074*
C9	0.4018 (4)	0.2751 (3)	0.9328 (6)	0.0490 (14)
H9	0.4596	0.2407	0.9302	0.059*
C10	0.4055 (4)	0.3543 (3)	0.8829 (6)	0.0417 (12)
C11	0.5644 (6)	0.5702 (3)	0.6675 (7)	0.083 (2)
H11A	0.4904	0.5796	0.5845	0.124*
H11B	0.6239	0.5792	0.6215	0.124*
H11C	0.5749	0.6052	0.7589	0.124*
C12	0.5855 (4)	0.3402 (3)	0.8040 (6)	0.0425 (12)
H12	0.6159	0.3564	0.7245	0.051*
C13	0.7872 (4)	0.1907 (3)	0.9535 (5)	0.0364 (11)
C14	0.8782 (4)	0.1572 (3)	0.8967 (6)	0.0338 (11)
C15	0.8636 (4)	0.1497 (3)	0.7312 (6)	0.0372 (12)
H15	0.7964	0.1678	0.6512	0.045*
C16	0.9484 (4)	0.1153 (3)	0.6847 (6)	0.0437 (12)
C17	1.0496 (5)	0.0893 (3)	0.8001 (7)	0.0605 (16)
H17	1.1066	0.0666	0.7671	0.073*
C18	1.0652 (5)	0.0975 (4)	0.9653 (7)	0.0758 (19)
H18	1.1335	0.0806	1.0446	0.091*
C19	0.9793 (5)	0.1309 (3)	1.0143 (6)	0.0548 (15)
H19	0.9898	0.1356	1.1261	0.066*
H2	0.731 (4)	0.266 (3)	0.764 (4)	0.066*

	U11	U22	U33	U12	U13	U23
Br1	0.0692 (4)	0.0859 (5)	0.0489 (3)	0.0221 (3)	0.0355 (3)	0.0008 (3)
N1	0.042 (2)	0.045 (3)	0.033 (2)	0.006 (2)	0.0207 (19)	−0.0008 (19)
N2	0.043 (3)	0.046 (3)	0.037 (2)	0.007 (2)	0.025 (2)	0.006 (2)
O1	0.089 (3)	0.047 (2)	0.068 (3)	−0.006 (2)	0.032 (2)	0.0087 (19)
O2	0.073 (2)	0.057 (2)	0.041 (2)	0.0126 (19)	0.0327 (19)	0.0088 (18)
C1	0.045 (3)	0.037 (3)	0.033 (3)	0.009 (3)	0.010 (2)	−0.003 (2)
C2	0.063 (4)	0.049 (4)	0.037 (3)	0.008 (3)	0.015 (3)	−0.003 (3)
C3	0.083 (5)	0.041 (4)	0.064 (4)	0.013 (4)	0.012 (4)	0.001 (3)
C4	0.058 (4)	0.069 (5)	0.071 (4)	0.026 (3)	0.015 (3)	−0.002 (3)
C5	0.048 (3)	0.051 (4)	0.040 (3)	0.009 (3)	0.010 (3)	0.000 (3)
C6	0.051 (4)	0.079 (5)	0.077 (4)	0.015 (3)	0.022 (3)	−0.007 (4)
C7	0.050 (4)	0.102 (6)	0.072 (4)	−0.001 (4)	0.032 (3)	0.001 (4)
C8	0.059 (4)	0.063 (4)	0.068 (4)	0.006 (3)	0.027 (3)	−0.002 (3)
C9	0.049 (4)	0.052 (4)	0.051 (3)	0.012 (3)	0.024 (3)	0.004 (3)
C10	0.041 (3)	0.046 (3)	0.037 (3)	0.011 (3)	0.011 (2)	−0.007 (2)
C11	0.127 (6)	0.051 (4)	0.071 (4)	−0.024 (4)	0.035 (4)	0.005 (3)
C12	0.052 (3)	0.046 (3)	0.032 (3)	0.003 (3)	0.018 (2)	−0.001 (2)
C13	0.047 (3)	0.038 (3)	0.029 (3)	0.000 (2)	0.018 (2)	0.000 (2)
C14	0.035 (3)	0.034 (3)	0.036 (3)	0.001 (2)	0.017 (2)	0.000 (2)
C15	0.034 (3)	0.036 (3)	0.043 (3)	0.001 (2)	0.016 (2)	0.001 (2)
C16	0.048 (3)	0.048 (3)	0.042 (3)	0.007 (3)	0.025 (3)	0.001 (2)
C17	0.046 (3)	0.079 (4)	0.061 (4)	0.018 (3)	0.025 (3)	0.001 (3)
C18	0.053 (4)	0.114 (6)	0.054 (4)	0.040 (4)	0.011 (3)	0.005 (4)
C19	0.062 (4)	0.069 (4)	0.034 (3)	0.011 (3)	0.017 (3)	0.001 (3)

Br1—C16	1.899 (5)	C7—H7	0.9300
N1—C12	1.282 (5)	C8—C9	1.356 (6)
N1—N2	1.392 (5)	C8—H8	0.9300
N2—C13	1.354 (6)	C9—C10	1.423 (6)
N2—H2	0.898 (10)	C9—H9	0.9300
O1—C2	1.372 (6)	C11—H11A	0.9600
O1—C11	1.439 (6)	C11—H11B	0.9600
O2—C13	1.228 (5)	C11—H11C	0.9600
C1—C2	1.389 (7)	C12—H12	0.9300
C1—C10	1.417 (6)	C13—C14	1.487 (6)
C1—C12	1.462 (6)	C14—C15	1.380 (6)
C2—C3	1.413 (7)	C14—C19	1.384 (6)
C3—C4	1.355 (7)	C15—C16	1.375 (6)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.408 (7)	C16—C17	1.377 (7)
C4—H4	0.9300	C17—C18	1.376 (7)
C5—C6	1.410 (7)	C17—H17	0.9300
C5—C10	1.418 (6)	C18—C19	1.393 (7)
C6—C7	1.351 (8)	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.401 (7)
C12—N1—N2	114.5 (4)	C1—C10—C9	124.6 (4)
C13—N2—N1	120.2 (4)	C5—C10—C9	115.9 (5)
C13—N2—H2	124 (3)	O1—C11—H11A	109.5
N1—N2—H2	114 (3)	O1—C11—H11B	109.5
C2—O1—C11	118.1 (5)	H11A—C11—H11B	109.5
C2—C1—C10	119.3 (5)	O1—C11—H11C	109.5
C2—C1—C12	116.0 (5)	H11A—C11—H11C	109.5
C10—C1—C12	124.7 (4)	H11B—C11—H11C	109.5
O1—C2—C1	116.3 (5)	N1—C12—C1	123.4 (4)
O1—C2—C3	122.3 (5)	N1—C12—H12	118.3
C1—C2—C3	121.4 (5)	C1—C12—H12	118.3
C4—C3—C2	118.7 (6)	O2—C13—N2	122.2 (4)
C4—C3—H3	120.6	O2—C13—C14	122.6 (4)
C2—C3—H3	120.6	N2—C13—C14	115.1 (4)
C3—C4—C5	122.7 (5)	C15—C14—C19	119.4 (4)
C3—C4—H4	118.7	C15—C14—C13	122.1 (4)
C5—C4—H4	118.7	C19—C14—C13	118.5 (4)
C4—C5—C6	120.4 (6)	C16—C15—C14	119.9 (4)
C4—C5—C10	118.5 (5)	C16—C15—H15	120.0
C6—C5—C10	121.1 (5)	C14—C15—H15	120.0
C7—C6—C5	120.5 (6)	C15—C16—C17	121.4 (4)
C7—C6—H6	119.7	C15—C16—Br1	117.8 (4)
C5—C6—H6	119.7	C17—C16—Br1	120.8 (4)
C6—C7—C8	119.6 (6)	C18—C17—C16	118.9 (5)
C6—C7—H7	120.2	C18—C17—H17	120.5
C8—C7—H7	120.2	C16—C17—H17	120.5
C9—C8—C7	121.0 (6)	C17—C18—C19	120.4 (5)
C9—C8—H8	119.5	C17—C18—H18	119.8
C7—C8—H8	119.5	C19—C18—H18	119.8
C8—C9—C10	121.8 (5)	C14—C19—C18	120.0 (5)
C8—C9—H9	119.1	C14—C19—H19	120.0
C10—C9—H9	119.1	C18—C19—H19	120.0
C1—C10—C5	119.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.90 (1)	2.10 (1)	2.989 (5)	174 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.90 (1)	2.10 (1)	2.989 (5)	174 (5)

Symmetry code: (i) .