3-Bromo-N′-[(2-meth­oxy­naphthalen-1-yl)methyl­idene]benzohydrazide

Li, H.-B.

doi:10.1107/S1600536811019349

organic compounds

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Volume 67| Part 6| June 2011| Page o1532

doi:10.1107/S1600536811019349

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3-Bromo-N′-[(2-methoxynaphthalen-1-yl)methylidene]benzohydrazide

He-Bing Li ^a ^*

^aDepartment of Chemistry and Life Sciences, Xiangnan University, Chenzhou 423000, People's Republic of China
^*Correspondence e-mail: lihebing07@163.com

(Received 21 May 2011; accepted 22 May 2011; online 28 May 2011)

The molecule of the title compound, C₁₉H₁₅BrN₂O₂, 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, molecules 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_r = 383.24
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.132
S = 1.00
3513 reflections
221 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.36 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

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

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

Supporting information file. DOI: 10.1107/S1600536811019349/hb5889Isup3.cml

checkCIF report

Comment top

In the last few years, the author has reported the sturctures of various hydrazone compounds (Li, 2008; Li, 2007a,b). As an extension of work on the structures of such compounds, the title new hydrazone compound is reported.

The bond lengths and bond angles in the title compound (Fig. 1) are within normal ranges (Allen et al., 1987) and comprable with those observed in similar compounds (Qiu et al., 2006; Yang & Guo, 2006; Yang, 2006). The dihedral angle between the C1—C10 naphthyl ring and C14—C19 benzene ring is 70.1 (2)°. The molecule of the compound adopts a trans configuration about the C12═N1 and C13—N2 bonds. In the crystal structure, the molecules are linked into chains along the c axis by N—H···O hydrogen bonds (Table 1 and Fig.2).

Related literature top

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

Experimental top

2-Methoxy-1-naphthaldehyde (0.1 mmol, 18.6 mg) and 3-bromobenzohydrazide (0.1 mmol, 21.5 mg) were dissolved in methanol (10 ml). The mixture was stirred at room temperature for 10 min to give a clear colorless solution. Colourless blocks of (I) were formed by gradual evaporation of the solvent over a week at room temperature (yield 63%).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

3-Bromo-N'-[(2-methoxynaphthalen-1-yl)methylidene]benzohydrazide top

Crystal data top

C₁₉H₁₅BrN₂O₂	F(000) = 776
M_r = 383.24	D_x = 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

Data collection top

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

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)] = 0.052	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(F_o²)] where P = (F_o² + 2F_c²)/3
3513 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₉H₁₅BrN₂O₂	V = 1703.3 (3) Å³
M_r = 383.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3562 (11) Å	µ = 2.43 mm⁻¹
b = 17.0404 (15) Å	T = 298 K
c = 8.6175 (10) Å	0.30 × 0.27 × 0.27 mm
β = 110.155 (2)°

Data collection top

Bruker SMART CCD diffractometer	3513 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1721 reflections with I > 2σ(I)
T_min = 0.530, T_max = 0.560	R_int = 0.080
9533 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	1 restraint
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.30 e Å⁻³
3513 reflections	Δρ_min = −0.36 e Å⁻³
221 parameters

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	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅BrN₂O₂
M_r	383.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.3562 (11), 17.0404 (15), 8.6175 (10)
β (°)	110.155 (2)
V (Å³)	1703.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.43
Crystal size (mm)	0.30 × 0.27 × 0.27

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.530, 0.560
No. of measured, independent and observed [I > 2σ(I)] reflections	9533, 3513, 1721
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.132, 1.00
No. of reflections	3513
No. of parameters	221
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)	0.30, −0.36

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.898 (10)	2.095 (13)	2.989 (5)	174 (5)

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

The author acknowledges a research grant from Xiangnan University.

References

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