(E)-3-Bromo-N′-(2-chloro­benzyl­idene)benzohydrazide

Qu, L.-Z.; Cao, G.-B.

doi:10.1107/S160053680902412X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1705

doi:10.1107/S160053680902412X

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(E)-3-Bromo-N′-(2-chlorobenzylidene)benzohydrazide

Lan-Zhu Qu ^a and Guo-Biao Cao ^a ^*

^aDepartment of Chemistry, Ankang University, Ankang Shanxi 725000, People's Republic of China
^*Correspondence e-mail: guobiao_cao@126.com

(Received 23 June 2009; accepted 23 June 2009; online 27 June 2009)

The title compound, C₁₄H₁₀BrClN₂O, was synthesized by the reaction of 2-chlorobenzaldehyde with an equimolar quantity of 3-bromobenzohydrazide in methanol. The molecule displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 13.0 (2)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains propagating along the c axis.

Related literature

For the 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 ); Cao & Lu (2009a ,b ).

Experimental

Crystal data

C₁₄H₁₀BrClN₂O
M_r = 337.60
Monoclinic, P 2₁ /c
a = 13.140 (1) Å
b = 12.632 (1) Å
c = 8.377 (1) Å
β = 98.174 (2)°
V = 1376.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 3.17 mm⁻¹
T = 298 K
0.27 × 0.25 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.481, T_max = 0.542 (expected range = 0.442–0.498)
8319 measured reflections
2998 independent reflections
2235 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.076
S = 1.03
2998 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.89 (1)	1.98 (1)	2.854 (2)	165 (3)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902412X/ci2833sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902412X/ci2833Isup2.hkl

checkCIF report

Comment top

Study on the crystal structures of hydrazone derivatives is a hot topic in structural chemistry. In the last few years, the crystal structures of a large number of hydrazone compounds have been reported (Mohd Lair et al., 2009; Fun et al., 2008; Li & Ban, 2009; Zhu et al., 2009; Yang, 2007; You et al., 2008). As a continuation of our work in this area (Qu et al., 2008; Yang et al., 2008; Cao & Lu, 2009a,b), the title new hydrazone compound derived from the reaction of 2-chlorobenzaldehyde with an equimolar quantity of 3-bromobenzohydrazide is reported.

In the title compound (Fig. 1), the dihedral angle between the two benzene rings is 13.0 (2)°. The molecule displays an E configuration about the C═N bond. In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1) to form chains running along the c axis (Fig. 2).

Related literature top

For the 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); Cao & Lu (2009a,b).

Experimental top

The title compound was prepared by refluxing equimolar quantities of 2-chlorobenzaldehyde with 3-bromobenzohydrazide in methanol. Colourless block-like crystals were formed by slow evaporation of the solution in air.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

(E)-3-Bromo-N'-(2-chlorobenzylidene)benzohydrazide top

Crystal data top

C₁₄H₁₀BrClN₂O	F(000) = 672
M_r = 337.60	D_x = 1.629 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2981 reflections
a = 13.140 (1) Å	θ = 2.2–27.5°
b = 12.632 (1) Å	µ = 3.17 mm⁻¹
c = 8.377 (1) Å	T = 298 K
β = 98.174 (2)°	Block, colourless
V = 1376.3 (2) Å³	0.27 × 0.25 × 0.22 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2998 independent reflections
Radiation source: fine-focus sealed tube	2235 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 27.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→15
T_min = 0.481, T_max = 0.542	k = −16→13
8319 measured reflections	l = −10→10

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.0266P)² + 0.7889P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
2998 reflections	Δρ_max = 0.52 e Å⁻³
176 parameters	Δρ_min = −0.65 e Å⁻³
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0155 (8)

Crystal data top

C₁₄H₁₀BrClN₂O	V = 1376.3 (2) Å³
M_r = 337.60	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.140 (1) Å	µ = 3.17 mm⁻¹
b = 12.632 (1) Å	T = 298 K
c = 8.377 (1) Å	0.27 × 0.25 × 0.22 mm
β = 98.174 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2998 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2235 reflections with I > 2σ(I)
T_min = 0.481, T_max = 0.542	R_int = 0.025
8319 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	1 restraint
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.52 e Å⁻³
2998 reflections	Δρ_min = −0.65 e Å⁻³
176 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	1.03493 (2)	0.63367 (3)	0.15480 (4)	0.06855 (15)
Cl1	0.71461 (6)	1.15851 (6)	0.46918 (11)	0.0757 (3)
N1	0.69113 (14)	0.83453 (15)	0.6106 (2)	0.0358 (4)
N2	0.74414 (15)	0.76627 (15)	0.5225 (2)	0.0378 (4)
O1	0.75662 (14)	0.64019 (12)	0.71573 (18)	0.0477 (4)
C1	0.62315 (16)	1.00731 (17)	0.6291 (3)	0.0342 (5)
C2	0.62851 (18)	1.11440 (19)	0.5940 (3)	0.0433 (6)
C3	0.5678 (2)	1.1884 (2)	0.6563 (3)	0.0542 (7)
H3	0.5732	1.2596	0.6310	0.065*
C4	0.4996 (2)	1.1563 (2)	0.7553 (3)	0.0572 (7)
H4	0.4581	1.2057	0.7970	0.069*
C5	0.4924 (2)	1.0510 (2)	0.7933 (3)	0.0523 (7)
H5	0.4459	1.0293	0.8607	0.063*
C6	0.55369 (18)	0.9775 (2)	0.7319 (3)	0.0429 (6)
H6	0.5487	0.9066	0.7596	0.052*
C7	0.68317 (17)	0.92838 (18)	0.5560 (3)	0.0367 (5)
H7	0.7159	0.9469	0.4686	0.044*
C8	0.77228 (16)	0.67075 (17)	0.5825 (2)	0.0336 (5)
C9	0.82605 (15)	0.60205 (17)	0.4763 (2)	0.0319 (5)
C10	0.89265 (16)	0.64395 (18)	0.3775 (3)	0.0359 (5)
H10	0.9036	0.7166	0.3742	0.043*
C11	0.94190 (17)	0.5767 (2)	0.2851 (3)	0.0395 (5)
C12	0.9267 (2)	0.4693 (2)	0.2864 (3)	0.0487 (6)
H12	0.9603	0.4249	0.2225	0.058*
C13	0.8606 (2)	0.4287 (2)	0.3844 (3)	0.0498 (6)
H13	0.8490	0.3561	0.3859	0.060*
C14	0.81123 (18)	0.49435 (18)	0.4804 (3)	0.0411 (5)
H14	0.7679	0.4658	0.5479	0.049*
H2	0.749 (2)	0.784 (2)	0.4206 (17)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0647 (2)	0.0867 (3)	0.0630 (2)	0.00759 (16)	0.03940 (15)	0.00891 (15)
Cl1	0.0682 (5)	0.0610 (5)	0.1056 (6)	0.0046 (4)	0.0393 (4)	0.0307 (4)
N1	0.0373 (10)	0.0395 (11)	0.0326 (9)	0.0065 (8)	0.0121 (8)	−0.0033 (8)
N2	0.0477 (11)	0.0400 (11)	0.0292 (9)	0.0105 (9)	0.0168 (8)	0.0004 (8)
O1	0.0696 (12)	0.0445 (10)	0.0339 (8)	0.0059 (8)	0.0236 (8)	0.0038 (7)
C1	0.0307 (11)	0.0393 (12)	0.0322 (11)	0.0033 (9)	0.0031 (9)	−0.0017 (9)
C2	0.0375 (12)	0.0439 (14)	0.0487 (14)	0.0022 (10)	0.0063 (10)	0.0019 (10)
C3	0.0551 (15)	0.0383 (14)	0.0686 (18)	0.0081 (12)	0.0063 (14)	−0.0028 (12)
C4	0.0551 (16)	0.0562 (17)	0.0609 (17)	0.0170 (13)	0.0102 (14)	−0.0140 (13)
C5	0.0474 (14)	0.0642 (18)	0.0484 (15)	0.0073 (13)	0.0175 (12)	−0.0042 (13)
C6	0.0429 (13)	0.0435 (14)	0.0443 (13)	0.0035 (11)	0.0127 (11)	−0.0016 (11)
C7	0.0383 (12)	0.0423 (14)	0.0314 (11)	0.0033 (10)	0.0114 (9)	0.0015 (10)
C8	0.0352 (11)	0.0369 (12)	0.0300 (11)	0.0002 (9)	0.0096 (9)	−0.0022 (9)
C9	0.0297 (11)	0.0382 (12)	0.0280 (10)	0.0051 (9)	0.0049 (8)	0.0002 (9)
C10	0.0369 (12)	0.0392 (12)	0.0329 (11)	0.0027 (10)	0.0088 (9)	−0.0006 (9)
C11	0.0341 (11)	0.0526 (15)	0.0336 (11)	0.0064 (10)	0.0112 (9)	0.0018 (10)
C12	0.0508 (14)	0.0518 (16)	0.0450 (14)	0.0149 (12)	0.0119 (11)	−0.0089 (12)
C13	0.0573 (15)	0.0353 (13)	0.0576 (15)	0.0054 (12)	0.0114 (12)	−0.0040 (11)
C14	0.0410 (13)	0.0413 (14)	0.0427 (13)	0.0021 (10)	0.0120 (10)	0.0025 (10)

Geometric parameters (Å, º) top

Br1—C11	1.892 (2)	C5—C6	1.376 (3)
Cl1—C2	1.738 (2)	C5—H5	0.93
N1—C7	1.270 (3)	C6—H6	0.93
N1—N2	1.386 (2)	C7—H7	0.93
N2—C8	1.339 (3)	C8—C9	1.491 (3)
N2—H2	0.893 (10)	C9—C14	1.376 (3)
O1—C8	1.226 (2)	C9—C10	1.392 (3)
C1—C2	1.388 (3)	C10—C11	1.372 (3)
C1—C6	1.393 (3)	C10—H10	0.93
C1—C7	1.459 (3)	C11—C12	1.372 (4)
C2—C3	1.378 (3)	C12—C13	1.376 (4)
C3—C4	1.366 (4)	C12—H12	0.93
C3—H3	0.93	C13—C14	1.379 (3)
C4—C5	1.374 (4)	C13—H13	0.93
C4—H4	0.93	C14—H14	0.93

C7—N1—N2	114.24 (17)	N1—C7—H7	119.7
C8—N2—N1	119.58 (17)	C1—C7—H7	119.7
C8—N2—H2	122 (2)	O1—C8—N2	123.53 (19)
N1—N2—H2	118 (2)	O1—C8—C9	121.02 (19)
C2—C1—C6	116.9 (2)	N2—C8—C9	115.44 (18)
C2—C1—C7	122.0 (2)	C14—C9—C10	119.6 (2)
C6—C1—C7	121.1 (2)	C14—C9—C8	118.69 (19)
C3—C2—C1	122.1 (2)	C10—C9—C8	121.7 (2)
C3—C2—Cl1	118.1 (2)	C11—C10—C9	119.2 (2)
C1—C2—Cl1	119.79 (18)	C11—C10—H10	120.4
C4—C3—C2	119.6 (2)	C9—C10—H10	120.4
C4—C3—H3	120.2	C10—C11—C12	121.8 (2)
C2—C3—H3	120.2	C10—C11—Br1	119.05 (18)
C3—C4—C5	120.1 (2)	C12—C11—Br1	119.17 (17)
C3—C4—H4	120.0	C11—C12—C13	118.6 (2)
C5—C4—H4	120.0	C11—C12—H12	120.7
C4—C5—C6	120.2 (2)	C13—C12—H12	120.7
C4—C5—H5	119.9	C12—C13—C14	120.8 (2)
C6—C5—H5	119.9	C12—C13—H13	119.6
C5—C6—C1	121.3 (2)	C14—C13—H13	119.6
C5—C6—H6	119.4	C9—C14—C13	120.0 (2)
C1—C6—H6	119.4	C9—C14—H14	120.0
N1—C7—C1	120.54 (19)	C13—C14—H14	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.89 (1)	1.98 (1)	2.854 (2)	165 (3)

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀BrClN₂O
M_r	337.60
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	13.140 (1), 12.632 (1), 8.377 (1)
β (°)	98.174 (2)
V (Å³)	1376.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.17
Crystal size (mm)	0.27 × 0.25 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.481, 0.542
No. of measured, independent and observed [I > 2σ(I)] reflections	8319, 2998, 2235
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.076, 1.03
No. of reflections	2998
No. of parameters	176
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)	0.52, −0.65

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.89 (1)	1.98 (1)	2.854 (2)	165 (3)

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

The Vital Foundation of Ankang University (Project No. 2008AKXY012) and the Special Scientific Research Foundation of the Education Office of Shanxi Province (Project No. 02 J K202) are gratefully acknowledged.

References

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