(E)-N′-(2-Chloro­benzyl­idene)-4-methoxy­benzohydrazide

Zhu, W.-D.; Chen, S.-W.

doi:10.1107/S1600536809037854

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2554

doi:10.1107/S1600536809037854

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(E)-N′-(2-Chlorobenzylidene)-4-methoxybenzohydrazide

Wen-Dong Zhu ^a ^* and Su-Wei Chen ^a

^aCollege of Agriculture and Life Sciences, Ankang University, Ankang Shanxi 725000, People's Republic of China
^*Correspondence e-mail: wendong_zhu@126.com

(Received 17 September 2009; accepted 18 September 2009; online 26 September 2009)

The molecule of the title compound, C₁₅H₁₃ClN₂O₂, adopts an E geometry about the C=N bond. The dihedral angle between the two benzene rings is 62.7 (2)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains running along the c axis.

Related literature

For the crystal structures of related hydrazone compounds, see: He & Liu (2005 ); Zhen & Han (2005 ); Fun et al. (2008 ); Qu & Cao (2009 ).

Experimental

Crystal data

C₁₅H₁₃ClN₂O₂
M_r = 288.72
Monoclinic, P 2₁ /c
a = 11.5488 (9) Å
b = 13.4244 (10) Å
c = 9.6207 (7) Å
β = 107.873 (4)°
V = 1419.57 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 298 K
0.23 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.940, T_max = 0.948
8562 measured reflections
3084 independent reflections
2304 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.133
S = 1.02
3084 reflections
185 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.901 (10)	1.994 (12)	2.8717 (17)	165 (2)
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/S1600536809037854/wn2348sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037854/wn2348Isup2.hkl

checkCIF report

Comment top

In recent years, the crystal structures of hydrazone compounds have attracted much attention (He & Liu, 2005; Zhen & Han, 2005; Fun et al., 2008; Qu & Cao, 2009). In this paper, the new title compound (Fig. 1) is reported.

The molecule of the title compound adopts an E geometry about the C7═N1 bond. The dihedral angle between the C1-C6 and C9-C14 benzene rings is 62.7 (2)°.

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 related hydrazone compounds, see: He & Liu (2005); Zhen & Han (2005); Fun et al. (2008); Qu & Cao (2009).

Experimental top

Equimolar quantities of 2-chlorobenzaldehyde and 4-methoxybenzohydrazide were refluxed in methanol. Colorless block-shaped 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 with ellipsoids drawn at the 30% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The molecular packing of the title compound, viewed along the b axis. Hydrogen bonds are drawn as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.

(E)-N'-(2-Chlorobenzylidene)-4-methoxybenzohydrazide top

Crystal data top

C₁₅H₁₃ClN₂O₂	F(000) = 600
M_r = 288.72	D_x = 1.351 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2779 reflections
a = 11.5488 (9) Å	θ = 2.4–27.4°
b = 13.4244 (10) Å	µ = 0.27 mm⁻¹
c = 9.6207 (7) Å	T = 298 K
β = 107.873 (4)°	Block, colorless
V = 1419.57 (18) Å³	0.23 × 0.23 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3084 independent reflections
Radiation source: fine-focus sealed tube	2304 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 27.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→12
T_min = 0.940, T_max = 0.948	k = −16→15
8562 measured reflections	l = −12→11

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0675P)² + 0.3322P] where P = (F_o² + 2F_c²)/3
3084 reflections	(Δ/σ)_max = 0.001
185 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₁₅H₁₃ClN₂O₂	V = 1419.57 (18) Å³
M_r = 288.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.5488 (9) Å	µ = 0.27 mm⁻¹
b = 13.4244 (10) Å	T = 298 K
c = 9.6207 (7) Å	0.23 × 0.23 × 0.20 mm
β = 107.873 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3084 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2304 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.948	R_int = 0.022
8562 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	1 restraint
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.19 e Å⁻³
3084 reflections	Δρ_min = −0.51 e Å⁻³
185 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	0.23118 (7)	1.10791 (5)	0.47212 (9)	0.0924 (3)
N1	0.19678 (13)	0.85010 (10)	0.71097 (14)	0.0399 (3)
N2	0.24583 (13)	0.76562 (10)	0.67022 (14)	0.0403 (3)
O1	0.29267 (12)	0.69949 (9)	0.89788 (12)	0.0479 (3)
O2	0.46641 (14)	0.34135 (10)	0.58877 (16)	0.0628 (4)
C1	0.12586 (16)	1.01500 (13)	0.65257 (19)	0.0447 (4)
C2	0.14399 (19)	1.10494 (14)	0.5909 (3)	0.0583 (5)
C3	0.0947 (2)	1.19280 (17)	0.6231 (3)	0.0813 (8)
H3	0.1089	1.2525	0.5820	0.098*
C4	0.0258 (3)	1.1916 (2)	0.7147 (4)	0.0884 (9)
H4	−0.0073	1.2506	0.7359	0.106*
C5	0.0045 (2)	1.1040 (2)	0.7763 (3)	0.0803 (8)
H5	−0.0431	1.1037	0.8386	0.096*
C6	0.05407 (18)	1.01637 (17)	0.7455 (2)	0.0567 (5)
H6	0.0393	0.9572	0.7874	0.068*
C7	0.18011 (16)	0.92262 (12)	0.62146 (18)	0.0413 (4)
H7	0.2024	0.9168	0.5367	0.050*
C8	0.29077 (15)	0.69279 (12)	0.77010 (17)	0.0370 (4)
C9	0.33550 (15)	0.60262 (11)	0.71352 (17)	0.0369 (4)
C10	0.29691 (16)	0.57429 (13)	0.56828 (18)	0.0432 (4)
H10	0.2421	0.6143	0.5002	0.052*
C11	0.33849 (17)	0.48743 (13)	0.52260 (19)	0.0469 (4)
H11	0.3109	0.4692	0.4247	0.056*
C12	0.42069 (17)	0.42791 (13)	0.6221 (2)	0.0460 (4)
C13	0.4634 (2)	0.45714 (15)	0.7671 (2)	0.0586 (5)
H13	0.5215	0.4188	0.8340	0.070*
C14	0.42027 (19)	0.54236 (14)	0.81211 (19)	0.0530 (5)
H14	0.4480	0.5603	0.9101	0.064*
C15	0.4283 (2)	0.31064 (15)	0.4399 (3)	0.0627 (6)
H15A	0.3420	0.3000	0.4082	0.094*
H15B	0.4689	0.2498	0.4304	0.094*
H15C	0.4484	0.3614	0.3809	0.094*
H2	0.260 (2)	0.7642 (19)	0.5831 (15)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0982 (5)	0.0642 (4)	0.1289 (6)	0.0040 (3)	0.0556 (5)	0.0324 (4)
N1	0.0465 (8)	0.0383 (7)	0.0371 (7)	0.0016 (6)	0.0163 (6)	−0.0040 (6)
N2	0.0580 (9)	0.0354 (7)	0.0325 (7)	0.0047 (6)	0.0210 (6)	0.0006 (6)
O1	0.0710 (8)	0.0470 (7)	0.0313 (6)	−0.0005 (6)	0.0239 (6)	0.0015 (5)
O2	0.0811 (10)	0.0446 (7)	0.0629 (9)	0.0194 (7)	0.0224 (7)	0.0000 (6)
C1	0.0416 (9)	0.0428 (9)	0.0427 (9)	0.0038 (7)	0.0026 (7)	−0.0065 (7)
C2	0.0513 (11)	0.0422 (10)	0.0734 (14)	0.0026 (8)	0.0073 (10)	−0.0011 (9)
C3	0.0709 (15)	0.0410 (12)	0.116 (2)	0.0081 (10)	0.0049 (15)	−0.0041 (12)
C4	0.0755 (17)	0.0652 (16)	0.114 (2)	0.0275 (13)	0.0131 (16)	−0.0280 (15)
C5	0.0658 (15)	0.090 (2)	0.0834 (17)	0.0276 (13)	0.0203 (13)	−0.0204 (14)
C6	0.0497 (11)	0.0618 (12)	0.0556 (11)	0.0110 (9)	0.0117 (9)	−0.0076 (9)
C7	0.0481 (9)	0.0388 (8)	0.0370 (8)	0.0014 (7)	0.0130 (7)	−0.0021 (7)
C8	0.0445 (9)	0.0373 (8)	0.0315 (8)	−0.0034 (7)	0.0149 (7)	0.0010 (6)
C9	0.0462 (9)	0.0358 (8)	0.0305 (8)	−0.0005 (7)	0.0144 (7)	0.0039 (6)
C10	0.0495 (10)	0.0426 (9)	0.0335 (8)	0.0077 (8)	0.0070 (7)	0.0011 (7)
C11	0.0557 (11)	0.0453 (9)	0.0364 (9)	0.0047 (8)	0.0092 (8)	−0.0058 (7)
C12	0.0553 (11)	0.0366 (8)	0.0487 (10)	0.0045 (8)	0.0199 (8)	0.0033 (7)
C13	0.0757 (14)	0.0529 (11)	0.0432 (10)	0.0211 (10)	0.0123 (9)	0.0116 (8)
C14	0.0746 (13)	0.0511 (11)	0.0301 (8)	0.0108 (9)	0.0114 (8)	0.0057 (8)
C15	0.0724 (14)	0.0442 (11)	0.0751 (14)	0.0017 (9)	0.0277 (11)	−0.0144 (10)

Geometric parameters (Å, º) top

Cl1—C2	1.740 (3)	C5—H5	0.9300
N1—C7	1.275 (2)	C6—H6	0.9300
N1—N2	1.3773 (19)	C7—H7	0.9300
N2—C8	1.357 (2)	C8—C9	1.483 (2)
N2—H2	0.901 (10)	C9—C10	1.383 (2)
O1—C8	1.2261 (19)	C9—C14	1.394 (2)
O2—C12	1.355 (2)	C10—C11	1.383 (2)
O2—C15	1.424 (3)	C10—H10	0.9300
C1—C2	1.389 (3)	C11—C12	1.378 (2)
C1—C6	1.394 (3)	C11—H11	0.9300
C1—C7	1.461 (2)	C12—C13	1.386 (3)
C2—C3	1.385 (3)	C13—C14	1.370 (3)
C3—C4	1.356 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.373 (4)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.379 (3)	C15—H15C	0.9600

C7—N1—N2	115.26 (14)	O1—C8—C9	121.78 (14)
C8—N2—N1	119.53 (13)	N2—C8—C9	115.37 (13)
C8—N2—H2	120.3 (16)	C10—C9—C14	117.97 (15)
N1—N2—H2	119.3 (16)	C10—C9—C8	123.68 (14)
C12—O2—C15	117.63 (15)	C14—C9—C8	118.35 (14)
C2—C1—C6	117.37 (18)	C11—C10—C9	121.14 (16)
C2—C1—C7	121.33 (18)	C11—C10—H10	119.4
C6—C1—C7	121.29 (17)	C9—C10—H10	119.4
C3—C2—C1	121.2 (2)	C12—C11—C10	120.04 (16)
C3—C2—Cl1	119.16 (19)	C12—C11—H11	120.0
C1—C2—Cl1	119.59 (15)	C10—C11—H11	120.0
C4—C3—C2	119.9 (2)	O2—C12—C11	124.65 (17)
C4—C3—H3	120.1	O2—C12—C13	115.91 (16)
C2—C3—H3	120.1	C11—C12—C13	119.43 (16)
C3—C4—C5	120.6 (2)	C14—C13—C12	120.20 (17)
C3—C4—H4	119.7	C14—C13—H13	119.9
C5—C4—H4	119.7	C12—C13—H13	119.9
C4—C5—C6	119.8 (3)	C13—C14—C9	121.14 (17)
C4—C5—H5	120.1	C13—C14—H14	119.4
C6—C5—H5	120.1	C9—C14—H14	119.4
C5—C6—C1	121.1 (2)	O2—C15—H15A	109.5
C5—C6—H6	119.4	O2—C15—H15B	109.5
C1—C6—H6	119.4	H15A—C15—H15B	109.5
N1—C7—C1	119.69 (16)	O2—C15—H15C	109.5
N1—C7—H7	120.2	H15A—C15—H15C	109.5
C1—C7—H7	120.2	H15B—C15—H15C	109.5
O1—C8—N2	122.83 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.90 (1)	1.99 (1)	2.8717 (17)	165 (2)

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃ClN₂O₂
M_r	288.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.5488 (9), 13.4244 (10), 9.6207 (7)
β (°)	107.873 (4)
V (Å³)	1419.57 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.23 × 0.23 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.940, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	8562, 3084, 2304
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.133, 1.02
No. of reflections	3084
No. of parameters	185
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)	0.19, −0.51

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	0.901 (10)	1.994 (12)	2.8717 (17)	165 (2)

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

The Scientific Research Project of the Education Office of Shanxi Province (Project No. 08JK213) is acknowledged for support of this study.

References

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