(E)-N′-(4-Methoxy­benzyl­idene)benzohydrazide

Gou, J.-X.; Song, M.-Z.; Fan, C.-G.; Yang, Z.-N.

doi:10.1107/S1600536809049988

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3207

doi:10.1107/S1600536809049988

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(E)-N′-(4-Methoxybenzylidene)benzohydrazide

Jian-Xia Gou,^a Ming-Zhi Song,^a,^b Chuan-Gang Fan ^a ^* and Zhong-Nian Yang ^a

^aCollege of Chemistry and Chemical Technology, Binzhou University, Binzhou 256600, Shandong, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266555, People's Republic of China
^*Correspondence e-mail: fanchuangang2009@163.com

(Received 24 October 2009; accepted 20 November 2009; online 25 November 2009)

In the title molecule, C₁₅H₁₄N₂O₂, the dihedral angle between the benzene rings is 5.93 (17)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains propagating in [010].

Related literature

For properties of Schiff base ligands, see: Cozzi et al. (2004 ). For related crystal structures, see: Fun et al. (2008 ); Cui et al. (2009 ); Nie (2008 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₂
M_r = 254.28
Orthorhombic, P c a 2₁
a = 31.414 (3) Å
b = 5.1067 (5) Å
c = 8.1336 (9) Å
V = 1304.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.49 × 0.48 × 0.30 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.958, T_max = 0.974
2220 measured reflections
1239 independent reflections
920 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.106
S = 1.03
1239 reflections
173 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.17	2.961 (2)	152
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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 I, global. DOI: 10.1107/S1600536809049988/bq2172sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049988/bq2172Isup2.hkl

checkCIF report

Comment top

Schiff bases are popular ligands in coordination chemistry due to their ease of synthesis and their ability to be readily modified both electronically and sterically. Mixed-donor Schiff bases have been used extensively in catalysis (Cozzi, 2004).

In (I), (Fig. 1), the bond lengths an angles are normal and are comparable to the values observed in similar compounds (Nie et al., 2008; Fun et al., 2008; Cui et al., 2009).

In the crystal structure, the C8=N2 bond length in the molecule is 1.269 (3) °, showing the double-bond character. Meanwhile, the dihedral angle between the benzene ring (C2-C7) and the benzene ring (C9-C14) in the Schiff base molecule is 5.93 (17) °, indicating that the two aromatic ring planes are almost coplanar. Moreover, the crystal supramolecular structure was built from the connections of weak intermolecular N—H···O hydrogen bonds, as shown in table 1, and these hydrogen bonds link molecules into one-dimensional chains propagated in direction [010].

Related literature top

For properties of Schiff base ligands, see: Cozzi et al. (2004). For related crystal structures, see: Fun et al. (2008); Cui et al. (2009); Nie (2008).

Experimental top

Benzohydrazide (5.0 mmol), 20 ml ethanol and 4-methoxybenzaldehyde (5.0 mmol) were mixed in 50 ml flash. After refluxing 3 h, the resulting mixture was cooled to room temperature, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C₁₅H₁₄N₂O₂: C 70.85, H 5.55, N 11.02%; found: C 70.78, H 5.64, N 11.13%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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. A view of (I) showing the atomic numbering scheme and 30% probability displacement ellipsoids.
	Fig. 2. The packing of (I) builted from the connections of weak intermolecular N—H···O hydrogen bonds with dashed lines.

(E)-N'-(4-Methoxybenzylidene)benzohydrazide top

Crystal data top

C₁₅H₁₄N₂O₂	F(000) = 536
M_r = 254.28	D_x = 1.294 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1475 reflections
a = 31.414 (3) Å	θ = 2.6–22.4°
b = 5.1067 (5) Å	µ = 0.09 mm⁻¹
c = 8.1336 (9) Å	T = 298 K
V = 1304.8 (2) Å³	Block, colourless
Z = 4	0.49 × 0.48 × 0.30 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1239 independent reflections
Radiation source: fine-focus sealed tube	920 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
phi and ω scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = 0→36
T_min = 0.958, T_max = 0.974	k = 0→6
2220 measured reflections	l = −9→9

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.051P)² + 0.0327P] where P = (F_o² + 2F_c²)/3
1239 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.18 e Å⁻³
1 restraint	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₂	V = 1304.8 (2) Å³
M_r = 254.28	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 31.414 (3) Å	µ = 0.09 mm⁻¹
b = 5.1067 (5) Å	T = 298 K
c = 8.1336 (9) Å	0.49 × 0.48 × 0.30 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1239 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	920 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.974	R_int = 0.037
2220 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.106	H-atom parameters constrained
S = 1.03	Δρ_max = 0.18 e Å⁻³
1239 reflections	Δρ_min = −0.14 e Å⁻³
173 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
N1	0.32900 (6)	0.0513 (4)	0.8803 (3)	0.0446 (6)
H1	0.3182	0.2051	0.8691	0.053*
N2	0.37282 (6)	0.0199 (4)	0.8715 (3)	0.0448 (6)
O1	0.31604 (5)	−0.3787 (3)	0.9244 (3)	0.0612 (6)
O2	0.57114 (5)	0.2572 (4)	0.8020 (3)	0.0618 (6)
C1	0.30295 (7)	−0.1548 (5)	0.9062 (4)	0.0414 (6)
C2	0.25645 (8)	−0.0907 (4)	0.9049 (4)	0.0404 (6)
C3	0.22924 (9)	−0.2535 (6)	0.9909 (4)	0.0522 (8)
H3	0.2400	−0.3961	1.0487	0.063*
C4	0.18566 (10)	−0.2029 (7)	0.9905 (5)	0.0688 (11)
H4	0.1673	−0.3098	1.0501	0.083*
C5	0.16978 (9)	0.0027 (7)	0.9031 (6)	0.0707 (10)
H5	0.1407	0.0366	0.9043	0.085*
C6	0.19643 (9)	0.1599 (6)	0.8133 (5)	0.0653 (10)
H6	0.1853	0.2959	0.7505	0.078*
C7	0.23964 (8)	0.1159 (5)	0.8162 (4)	0.0506 (8)
H7	0.2577	0.2262	0.7579	0.061*
C8	0.39287 (8)	0.2202 (5)	0.8213 (4)	0.0437 (7)
H8	0.3775	0.3676	0.7898	0.052*
C9	0.43914 (7)	0.2271 (5)	0.8114 (4)	0.0399 (6)
C10	0.46450 (8)	0.0478 (5)	0.8944 (4)	0.0478 (7)
H10	0.4517	−0.0854	0.9547	0.057*
C11	0.50810 (8)	0.0635 (5)	0.8889 (4)	0.0479 (7)
H11	0.5245	−0.0577	0.9460	0.058*
C12	0.52766 (7)	0.2591 (5)	0.7988 (4)	0.0420 (6)
C13	0.50332 (9)	0.4391 (5)	0.7160 (4)	0.0472 (7)
H13	0.5163	0.5708	0.6550	0.057*
C14	0.45933 (8)	0.4235 (5)	0.7239 (4)	0.0485 (8)
H14	0.4430	0.5479	0.6691	0.058*
C15	0.59304 (9)	0.4528 (7)	0.7113 (5)	0.0735 (10)
H15A	0.5848	0.4435	0.5978	0.110*
H15B	0.6232	0.4249	0.7203	0.110*
H15C	0.5860	0.6224	0.7544	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0362 (12)	0.0317 (11)	0.0658 (16)	0.0055 (9)	−0.0014 (13)	0.0011 (12)
N2	0.0331 (12)	0.0412 (12)	0.0600 (16)	0.0020 (10)	−0.0012 (13)	−0.0067 (12)
O1	0.0481 (10)	0.0330 (10)	0.1026 (18)	0.0060 (8)	−0.0035 (13)	0.0002 (12)
O2	0.0379 (11)	0.0707 (13)	0.0766 (14)	−0.0043 (10)	−0.0008 (12)	0.0158 (12)
C1	0.0410 (13)	0.0339 (13)	0.0492 (17)	−0.0011 (12)	−0.0008 (16)	−0.0051 (15)
C2	0.0402 (14)	0.0369 (13)	0.0439 (17)	−0.0002 (11)	−0.0016 (15)	−0.0060 (16)
C3	0.0510 (18)	0.0496 (17)	0.056 (2)	−0.0085 (14)	0.0014 (16)	−0.0045 (16)
C4	0.050 (2)	0.082 (3)	0.075 (3)	−0.0216 (18)	0.0150 (19)	−0.018 (2)
C5	0.0399 (16)	0.079 (2)	0.093 (3)	0.0042 (16)	−0.011 (2)	−0.022 (3)
C6	0.0501 (19)	0.060 (2)	0.086 (3)	0.0124 (16)	−0.0138 (19)	−0.009 (2)
C7	0.0453 (17)	0.0448 (15)	0.062 (2)	0.0023 (13)	−0.0056 (16)	−0.0029 (17)
C8	0.0398 (14)	0.0357 (14)	0.0556 (19)	0.0035 (12)	−0.0036 (14)	0.0009 (14)
C9	0.0398 (14)	0.0342 (14)	0.0456 (16)	0.0011 (12)	0.0002 (15)	−0.0049 (14)
C10	0.0451 (15)	0.0416 (14)	0.0566 (19)	0.0012 (12)	0.0025 (17)	0.0087 (18)
C11	0.0428 (15)	0.0446 (15)	0.0563 (19)	0.0049 (12)	−0.0057 (17)	0.0068 (18)
C12	0.0336 (15)	0.0442 (15)	0.0482 (16)	−0.0017 (13)	0.0013 (15)	−0.0061 (14)
C13	0.0444 (17)	0.0428 (17)	0.0542 (19)	−0.0055 (13)	0.0028 (16)	0.0076 (15)
C14	0.0444 (18)	0.0408 (16)	0.060 (2)	0.0063 (13)	−0.0031 (16)	0.0051 (15)
C15	0.0471 (19)	0.081 (2)	0.092 (3)	−0.0165 (16)	−0.0041 (18)	0.013 (2)

Geometric parameters (Å, º) top

N1—C1	1.350 (3)	C6—H6	0.9300
N1—N2	1.388 (2)	C7—H7	0.9300
N1—H1	0.8600	C8—C9	1.456 (3)
N2—C8	1.269 (3)	C8—H8	0.9300
O1—C1	1.224 (3)	C9—C14	1.384 (4)
O2—C12	1.366 (3)	C9—C10	1.389 (4)
O2—C15	1.420 (4)	C10—C11	1.373 (3)
C1—C2	1.497 (3)	C10—H10	0.9300
C2—C3	1.382 (4)	C11—C12	1.383 (4)
C2—C7	1.383 (3)	C11—H11	0.9300
C3—C4	1.393 (4)	C12—C13	1.372 (4)
C3—H3	0.9300	C13—C14	1.386 (4)
C4—C5	1.363 (5)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.370 (5)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—C7	1.376 (4)	C15—H15C	0.9600

C1—N1—N2	121.29 (19)	N2—C8—H8	118.9
C1—N1—H1	119.4	C9—C8—H8	118.9
N2—N1—H1	119.4	C14—C9—C10	117.7 (2)
C8—N2—N1	114.6 (2)	C14—C9—C8	120.2 (2)
C12—O2—C15	118.0 (2)	C10—C9—C8	122.0 (3)
O1—C1—N1	122.9 (2)	C11—C10—C9	121.2 (3)
O1—C1—C2	122.2 (2)	C11—C10—H10	119.4
N1—C1—C2	114.8 (2)	C9—C10—H10	119.4
C3—C2—C7	119.1 (2)	C10—C11—C12	120.2 (3)
C3—C2—C1	117.9 (2)	C10—C11—H11	119.9
C7—C2—C1	122.9 (2)	C12—C11—H11	119.9
C2—C3—C4	119.7 (3)	O2—C12—C13	124.8 (3)
C2—C3—H3	120.2	O2—C12—C11	115.4 (2)
C4—C3—H3	120.2	C13—C12—C11	119.8 (2)
C5—C4—C3	120.3 (3)	C12—C13—C14	119.7 (3)
C5—C4—H4	119.9	C12—C13—H13	120.2
C3—C4—H4	119.9	C14—C13—H13	120.2
C4—C5—C6	120.4 (3)	C9—C14—C13	121.5 (3)
C4—C5—H5	119.8	C9—C14—H14	119.2
C6—C5—H5	119.8	C13—C14—H14	119.2
C5—C6—C7	119.9 (3)	O2—C15—H15A	109.5
C5—C6—H6	120.1	O2—C15—H15B	109.5
C7—C6—H6	120.1	H15A—C15—H15B	109.5
C6—C7—C2	120.7 (3)	O2—C15—H15C	109.5
C6—C7—H7	119.7	H15A—C15—H15C	109.5
C2—C7—H7	119.7	H15B—C15—H15C	109.5
N2—C8—C9	122.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.17	2.961 (2)	152

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₂
M_r	254.28
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	298
a, b, c (Å)	31.414 (3), 5.1067 (5), 8.1336 (9)
V (Å³)	1304.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.49 × 0.48 × 0.30

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.958, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	2220, 1239, 920
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.106, 1.03
No. of reflections	1239
No. of parameters	173
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.14

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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
N1—H1···O1ⁱ	0.86	2.17	2.961 (2)	152.1

Symmetry code: (i) x, y+1, z.

Acknowledgements

The authors acknowledge the financial support of the Foundation of Binzhou University.

References

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