N′-(2-Chloro­benzyl­idene)-4-methyl­benzohydrazide

Wang, D.-C.; Li, X.-R.; Gao, L.; Hai, Y.; Wang, J.-N.

doi:10.1107/S1600536812024099

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1960

doi:10.1107/S1600536812024099

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N′-(2-Chlorobenzylidene)-4-methylbenzohydrazide

De-Cheng Wang,^a Xiao-Rong Li,^b Lei Gao,^b Yong Hai ^c ^* and Jiang-Ning Wang ^b ^*

^aCapital Medical University, Beijing 100069, People's Republic of China, ^bCentral Laboratory, Luhe Teaching Hospital of the Capital Medical University, Beijing 101100, People's Republic of China, and ^cBeijing Chao-Yang Hospital, Beijing 100020, People's Republic of China
^*Correspondence e-mail: haiyong136@163.com, wangjiangning135@163.com

(Received 22 May 2012; accepted 26 May 2012; online 31 May 2012)

In the title compound, C₁₅H₁₃ClN₂O, the molecule displays a trans conformation with respect to the C=N bond. The two aromatic rings form a dihedral angle of 12.0 (3)°. In the crystal, molecules are connected via N—H⋯O hydrogen bonds into chains propagating along the c-axis direction.

Related literature

For the crystal structures of hydrazones, see: Wardell et al. (2006 ); Kummerle et al. (2009 ). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₅H₁₃ClN₂O
M_r = 272.72
Monoclinic, P 2₁ /c
a = 11.0697 (14) Å
b = 13.4436 (16) Å
c = 9.1643 (11) Å
β = 96.576 (2)°
V = 1354.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 298 K
0.10 × 0.10 × 0.07 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.973, T_max = 0.981
11486 measured reflections
2096 independent reflections
1682 reflections with I > 2σ(I)
R_int = 0.026
θ_max = 23.9°

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.104
S = 1.03
2096 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.90 (1)	2.05 (1)	2.8976 (19)	159 (2)
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/S1600536812024099/hb6816sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812024099/hb6816Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812024099/hb6816Isup3.cml

checkCIF report

Comment top

Recently, a number of hydrazones have been prepared and structurally characterized (Wardell et al., 2006; Kummerle et al., 2009). As an extension of work on the structural characterization of hydrazones, the title compound, Fig. 1, is reported here.

The molecule of the compound displays a trans conformation with respect to the C=N bond. The two aromatic rings form a dihedral angle of 12.0 (3)°. The bond lengths are within normal ranges (Allen et al., 1987). In the crystal, molecules are connected via intermolecular N—H···O hydrogen bonding (Table 1) into chains along the c axis (Fig. 2).

Related literature top

For the crystal structures of hydrazones, see: Wardell et al. (2006); Kummerle et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

2-Chlorobenzaldehyde (0.1 mmol, 14.0 mg) and 4-methylbenzhydrazide (0.1 mmol, 15.0 mg) were stirred in 20 ml methanol at room temperature for 30 min. A large number of colorless blocks were formed by slow evaporation of the methanolic solution containing the compound in air.

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 displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the b axis. Dashed lines show intermolecular hydrogen bonds.

N'-(2-Chlorobenzylidene)-4-methylbenzohydrazide top

Crystal data top

C₁₅H₁₃ClN₂O	F(000) = 568
M_r = 272.72	D_x = 1.337 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5323 reflections
a = 11.0697 (14) Å	θ = 2.4–24.3°
b = 13.4436 (16) Å	µ = 0.28 mm⁻¹
c = 9.1643 (11) Å	T = 298 K
β = 96.576 (2)°	Block, colorless
V = 1354.8 (3) Å³	0.10 × 0.10 × 0.07 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2096 independent reflections
Radiation source: fine-focus sealed tube	1682 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 23.9°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
T_min = 0.973, T_max = 0.981	k = −15→15
11486 measured reflections	l = −9→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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.051P)² + 0.4392P] where P = (F_o² + 2F_c²)/3
2096 reflections	(Δ/σ)_max < 0.001
176 parameters	Δρ_max = 0.16 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₅H₁₃ClN₂O	V = 1354.8 (3) Å³
M_r = 272.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.0697 (14) Å	µ = 0.28 mm⁻¹
b = 13.4436 (16) Å	T = 298 K
c = 9.1643 (11) Å	0.10 × 0.10 × 0.07 mm
β = 96.576 (2)°

Data collection top

Bruker SMART CCD diffractometer	2096 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1682 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.981	R_int = 0.026
11486 measured reflections	θ_max = 23.9°

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.16 e Å⁻³
2096 reflections	Δρ_min = −0.18 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
Cl1	0.73671 (7)	−0.12300 (4)	0.12887 (7)	0.0804 (3)
N1	0.68758 (14)	0.16431 (11)	−0.06660 (16)	0.0437 (4)
N2	0.73084 (15)	0.24311 (11)	0.02057 (16)	0.0440 (4)
O1	0.76428 (13)	0.33102 (10)	−0.18063 (13)	0.0560 (4)
C1	0.62975 (16)	−0.00454 (13)	−0.0883 (2)	0.0444 (5)
C2	0.65016 (18)	−0.10128 (14)	−0.0383 (2)	0.0508 (5)
C3	0.6060 (2)	−0.18270 (15)	−0.1196 (2)	0.0611 (6)
H3	0.6209	−0.2467	−0.0835	0.073*
C4	0.5403 (2)	−0.16849 (17)	−0.2538 (3)	0.0673 (6)
H4	0.5098	−0.2229	−0.3088	0.081*
C5	0.5195 (2)	−0.07398 (17)	−0.3069 (2)	0.0655 (6)
H5	0.4752	−0.0645	−0.3984	0.079*
C6	0.56356 (18)	0.00679 (16)	−0.2258 (2)	0.0548 (5)
H6	0.5489	0.0704	−0.2636	0.066*
C7	0.67597 (17)	0.08183 (13)	−0.0024 (2)	0.0453 (5)
H7	0.6967	0.0764	0.0986	0.054*
C8	0.76952 (17)	0.32495 (13)	−0.04646 (19)	0.0415 (4)
C9	0.81732 (17)	0.40832 (12)	0.04982 (19)	0.0404 (4)
C10	0.86287 (18)	0.39728 (13)	0.1951 (2)	0.0455 (5)
H10	0.8641	0.3347	0.2385	0.055*
C11	0.90664 (18)	0.47857 (15)	0.2764 (2)	0.0534 (5)
H11	0.9381	0.4694	0.3740	0.064*
C12	0.90528 (18)	0.57268 (14)	0.2177 (2)	0.0527 (5)
C13	0.8605 (2)	0.58265 (16)	0.0728 (3)	0.0707 (7)
H13	0.8585	0.6454	0.0299	0.085*
C14	0.8183 (2)	0.50216 (15)	−0.0111 (2)	0.0661 (6)
H14	0.7903	0.5111	−0.1098	0.079*
C15	0.9510 (2)	0.66110 (18)	0.3086 (3)	0.0776 (7)
H15A	0.9073	0.6662	0.3930	0.116*
H15B	0.9387	0.7205	0.2507	0.116*
H15C	1.0362	0.6530	0.3402	0.116*
H2	0.740 (2)	0.2368 (18)	0.1184 (11)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1227 (6)	0.0485 (4)	0.0643 (4)	0.0043 (3)	−0.0136 (4)	0.0008 (3)
N1	0.0568 (10)	0.0352 (8)	0.0386 (9)	−0.0009 (7)	0.0025 (7)	−0.0062 (7)
N2	0.0665 (10)	0.0329 (8)	0.0319 (8)	−0.0025 (7)	0.0022 (8)	−0.0019 (7)
O1	0.0919 (11)	0.0446 (8)	0.0314 (7)	−0.0007 (7)	0.0065 (7)	0.0009 (6)
C1	0.0503 (11)	0.0411 (10)	0.0433 (11)	−0.0045 (8)	0.0118 (9)	−0.0052 (8)
C2	0.0595 (12)	0.0430 (11)	0.0510 (12)	−0.0032 (9)	0.0104 (10)	−0.0071 (9)
C3	0.0737 (14)	0.0397 (11)	0.0710 (15)	−0.0060 (10)	0.0132 (12)	−0.0104 (10)
C4	0.0755 (15)	0.0543 (14)	0.0714 (16)	−0.0171 (11)	0.0052 (13)	−0.0230 (12)
C5	0.0703 (15)	0.0673 (15)	0.0565 (13)	−0.0130 (11)	−0.0027 (11)	−0.0109 (11)
C6	0.0607 (12)	0.0499 (12)	0.0528 (12)	−0.0068 (10)	0.0028 (10)	−0.0039 (10)
C7	0.0591 (12)	0.0387 (10)	0.0380 (10)	−0.0013 (9)	0.0054 (9)	−0.0036 (8)
C8	0.0542 (11)	0.0357 (10)	0.0343 (10)	0.0069 (8)	0.0044 (8)	0.0016 (8)
C9	0.0508 (11)	0.0338 (9)	0.0373 (10)	0.0016 (8)	0.0074 (8)	0.0007 (7)
C10	0.0599 (12)	0.0358 (10)	0.0404 (11)	−0.0023 (8)	0.0033 (9)	0.0043 (8)
C11	0.0643 (13)	0.0512 (12)	0.0427 (11)	−0.0079 (10)	−0.0019 (9)	−0.0029 (9)
C12	0.0534 (12)	0.0444 (12)	0.0610 (13)	−0.0091 (9)	0.0099 (10)	−0.0072 (10)
C13	0.1038 (19)	0.0339 (11)	0.0721 (16)	−0.0111 (11)	0.0008 (14)	0.0086 (10)
C14	0.1066 (18)	0.0429 (12)	0.0456 (12)	−0.0066 (12)	−0.0057 (12)	0.0091 (10)
C15	0.0850 (17)	0.0563 (14)	0.0914 (19)	−0.0249 (12)	0.0092 (14)	−0.0196 (13)

Geometric parameters (Å, º) top

Cl1—C2	1.736 (2)	C7—H7	0.9300
N1—C7	1.269 (2)	C8—C9	1.486 (2)
N1—N2	1.379 (2)	C9—C10	1.376 (3)
N2—C8	1.353 (2)	C9—C14	1.380 (3)
N2—H2	0.895 (9)	C10—C11	1.379 (3)
O1—C8	1.227 (2)	C10—H10	0.9300
C1—C2	1.389 (3)	C11—C12	1.374 (3)
C1—C6	1.391 (3)	C11—H11	0.9300
C1—C7	1.462 (2)	C12—C13	1.370 (3)
C2—C3	1.382 (3)	C12—C15	1.505 (3)
C3—C4	1.368 (3)	C13—C14	1.377 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.371 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.374 (3)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—H6	0.9300

C7—N1—N2	116.71 (15)	O1—C8—C9	121.18 (16)
C8—N2—N1	117.93 (14)	N2—C8—C9	116.96 (15)
C8—N2—H2	121.8 (16)	C10—C9—C14	118.10 (17)
N1—N2—H2	119.9 (16)	C10—C9—C8	123.99 (15)
C2—C1—C6	116.78 (17)	C14—C9—C8	117.90 (16)
C2—C1—C7	122.13 (17)	C9—C10—C11	120.29 (17)
C6—C1—C7	121.09 (17)	C9—C10—H10	119.9
C3—C2—C1	121.96 (19)	C11—C10—H10	119.9
C3—C2—Cl1	117.91 (16)	C12—C11—C10	122.04 (18)
C1—C2—Cl1	120.10 (14)	C12—C11—H11	119.0
C4—C3—C2	119.5 (2)	C10—C11—H11	119.0
C4—C3—H3	120.2	C13—C12—C11	117.12 (18)
C2—C3—H3	120.2	C13—C12—C15	121.4 (2)
C3—C4—C5	119.95 (19)	C11—C12—C15	121.5 (2)
C3—C4—H4	120.0	C12—C13—C14	121.75 (19)
C5—C4—H4	120.0	C12—C13—H13	119.1
C4—C5—C6	120.4 (2)	C14—C13—H13	119.1
C4—C5—H5	119.8	C13—C14—C9	120.66 (19)
C6—C5—H5	119.8	C13—C14—H14	119.7
C5—C6—C1	121.4 (2)	C9—C14—H14	119.7
C5—C6—H6	119.3	C12—C15—H15A	109.5
C1—C6—H6	119.3	C12—C15—H15B	109.5
N1—C7—C1	119.45 (16)	H15A—C15—H15B	109.5
N1—C7—H7	120.3	C12—C15—H15C	109.5
C1—C7—H7	120.3	H15A—C15—H15C	109.5
O1—C8—N2	121.86 (16)	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.90 (1)	2.05 (1)	2.8976 (19)	159 (2)

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃ClN₂O
M_r	272.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.0697 (14), 13.4436 (16), 9.1643 (11)
β (°)	96.576 (2)
V (Å³)	1354.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.10 × 0.10 × 0.07

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.973, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	11486, 2096, 1682
R_int	0.026
θ_max (°)	23.9
(sin θ/λ)_max (Å⁻¹)	0.569

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.104, 1.03
No. of reflections	2096
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)	0.16, −0.18

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···O1ⁱ	0.895 (9)	2.045 (13)	2.8976 (19)	159 (2)

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

This work was supported by National Natural Science Foundation of China (81071586).

References

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