4-Hydr­oxy-N′-(4-methoxy­benzyl­idene)benzohydrazide

Shi, D.-H.

doi:10.1107/S1600536809030621

organic compounds

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Volume 65| Part 9| September 2009| Page o2107

doi:10.1107/S1600536809030621

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4-Hydroxy-N′-(4-methoxybenzylidene)benzohydrazide

Da-Hua Shi ^a ^*

^aSchool of Chemical Engineering, Huaihai Institute of Technology, Lianyungang Jiangsu 222005, People's Republic of China
^*Correspondence e-mail: shidahua@yahoo.cn

(Received 31 July 2009; accepted 1 August 2009; online 8 August 2009)

The title compound, C₁₅H₁₄N₂O₃, was synthesized by the reaction of 4-methoxybenzaldehyde with 4-hydroxybenzohydrazide in methanol. The molecule adopts an E configuration about the C=N bond. The two benzene rings make a dihedral angle of 46.6 (2)°. In the crystal structure, molecules are linked into a two-dimensional network parallel to (001) through O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For the antibacterial activity of hydrazone compounds, see: Cukurovali et al. (2006 ). For crystal structures of hydrazone compounds, see: Abdul Alhadi et al. (2009 ); Mohd Lair et al. (2009 ); Cao & Lu (2009 ); Qu & Cao (2009 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₃
M_r = 270.28
Orthorhombic, P b c a
a = 11.947 (2) Å
b = 7.555 (1) Å
c = 29.452 (2) Å
V = 2658.3 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.981, T_max = 0.984
15205 measured reflections
2897 independent reflections
2030 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.103
S = 1.04
2897 reflections
187 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.82	1.91	2.7271 (15)	171
N2—H2A⋯O2ⁱⁱ	0.90 (1)	2.12 (1)	3.0216 (17)	173 (2)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ .

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/S1600536809030621/ci2875sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809030621/ci2875Isup2.hkl

checkCIF report

Comment top

Hydrazone compounds are a kind of important materials in biological and medicinal chemistry. They have been widely investigated for their antibacterial activities (Cukurovali et al., 2006). Recently, a number of hydrazone compounds have been prepared and structurally characterized (Abdul Alhadi et al., 2009; Mohd Lair et al., 2009; Cao & Lu, 2009; Qu & Cao, 2009). In this paper, the author reports the crystal structure of the title hydrazone compound.

The molecule of the title compound adopts an E configuration about the C═N bond (Fig. 1). The two benzene rings make a dihedral angle of 46.56 (7)°. The C8/N1/N2/C9/O2 plane makes dihedral angles of 8.2 (1) and 54.5 (1)°, respectively, with the C1—C6 and C10—C15 benzene rings. All the bond lengths are normal (Allen et al., 1987).

In the crystal structure, molecules are linked through N—H···O and O—H···O hydrogen bonds (Table 1), forming a two-dimensional network parallel to the (001) [Fig. 2].

Related literature top

For the antibacterial activity of hydrazone compounds, see: Cukurovali et al. (2006). For crystal structures of hydrazone compounds, see: Abdul Alhadi et al. (2009); Mohd Lair et al. (2009); Cao & Lu (2009); Qu & Cao (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

4-Methoxybenzaldehyde (13.6 mg, 0.1 mmol) and 4-hydroxybenzohydrazide (15.2 mg, 0.1 mmol) were mixed and refluxed in a methanol solution. After 30 min, the clear solution was evaporated to give colourless crystallites, which were recrystallized from methanol to form single crystals.

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 molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

4-Hydroxy-N'-(4-methoxybenzylidene)benzohydrazide top

Crystal data top

C₁₅H₁₄N₂O₃	F(000) = 1136
M_r = 270.28	D_x = 1.351 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2853 reflections
a = 11.947 (2) Å	θ = 2.6–25.0°
b = 7.555 (1) Å	µ = 0.10 mm⁻¹
c = 29.452 (2) Å	T = 298 K
V = 2658.3 (6) Å³	Block, colourless
Z = 8	0.20 × 0.20 × 0.17 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2897 independent reflections
Radiation source: fine-focus sealed tube	2030 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω scans	θ_max = 27.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→15
T_min = 0.981, T_max = 0.984	k = −9→9
15205 measured reflections	l = −33→37

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0418P)² + 0.5702P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2897 reflections	Δρ_max = 0.18 e Å⁻³
187 parameters	Δρ_min = −0.15 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: 0.0025 (7)

Crystal data top

C₁₅H₁₄N₂O₃	V = 2658.3 (6) Å³
M_r = 270.28	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.947 (2) Å	µ = 0.10 mm⁻¹
b = 7.555 (1) Å	T = 298 K
c = 29.452 (2) Å	0.20 × 0.20 × 0.17 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2897 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2030 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.984	R_int = 0.035
15205 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.18 e Å⁻³
2897 reflections	Δρ_min = −0.15 e Å⁻³
187 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	0.77001 (10)	0.20495 (17)	0.58903 (4)	0.0428 (3)
N2	0.75665 (11)	0.28526 (17)	0.63096 (4)	0.0427 (3)
O1	0.93859 (13)	0.00418 (19)	0.39100 (4)	0.0755 (4)
O2	0.60541 (8)	0.11510 (14)	0.64634 (3)	0.0460 (3)
O3	0.61014 (9)	0.54911 (17)	0.82831 (3)	0.0535 (3)
H3	0.5439	0.5709	0.8329	0.080*
C1	0.86784 (12)	0.2014 (2)	0.51899 (5)	0.0407 (4)
C2	0.79314 (13)	0.0874 (2)	0.49804 (5)	0.0487 (4)
H2	0.7279	0.0556	0.5132	0.058*
C3	0.81269 (14)	0.0203 (2)	0.45558 (5)	0.0535 (4)
H3A	0.7616	−0.0568	0.4423	0.064*
C4	0.90936 (15)	0.0683 (2)	0.43253 (5)	0.0518 (4)
C5	0.98315 (15)	0.1872 (2)	0.45215 (6)	0.0567 (5)
H5	1.0465	0.2232	0.4363	0.068*
C6	0.96304 (14)	0.2522 (2)	0.49499 (6)	0.0498 (4)
H6	1.0135	0.3308	0.5081	0.060*
C7	0.8819 (2)	−0.1482 (3)	0.37488 (7)	0.0800 (6)
H7A	0.8849	−0.2396	0.3975	0.120*
H7B	0.9171	−0.1893	0.3476	0.120*
H7C	0.8052	−0.1190	0.3687	0.120*
C8	0.84886 (12)	0.2682 (2)	0.56475 (5)	0.0426 (4)
H8	0.8944	0.3574	0.5763	0.051*
C9	0.67022 (11)	0.23670 (19)	0.65719 (5)	0.0363 (3)
C10	0.65784 (11)	0.33283 (19)	0.70077 (5)	0.0359 (3)
C11	0.74372 (12)	0.3390 (2)	0.73227 (5)	0.0418 (4)
H11	0.8139	0.2948	0.7247	0.050*
C12	0.72609 (12)	0.4102 (2)	0.77481 (5)	0.0460 (4)
H12	0.7839	0.4114	0.7960	0.055*
C13	0.62246 (12)	0.4800 (2)	0.78614 (5)	0.0391 (4)
C14	0.53678 (12)	0.4772 (2)	0.75443 (5)	0.0414 (4)
H14	0.4675	0.5261	0.7615	0.050*
C15	0.55430 (12)	0.4021 (2)	0.71250 (5)	0.0422 (4)
H15	0.4958	0.3977	0.6917	0.051*
H2A	0.8008 (14)	0.3787 (19)	0.6374 (6)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0453 (7)	0.0455 (8)	0.0375 (7)	−0.0003 (6)	0.0089 (6)	−0.0040 (6)
N2	0.0450 (7)	0.0437 (7)	0.0393 (7)	−0.0044 (6)	0.0098 (6)	−0.0066 (6)
O1	0.1010 (11)	0.0751 (10)	0.0503 (8)	−0.0109 (8)	0.0234 (7)	−0.0152 (6)
O2	0.0436 (6)	0.0499 (7)	0.0447 (6)	−0.0074 (5)	0.0081 (5)	−0.0078 (5)
O3	0.0464 (6)	0.0737 (8)	0.0404 (6)	0.0078 (6)	0.0045 (5)	−0.0117 (5)
C1	0.0425 (8)	0.0401 (8)	0.0396 (8)	0.0018 (7)	0.0081 (6)	0.0033 (6)
C2	0.0471 (9)	0.0513 (10)	0.0478 (9)	−0.0039 (8)	0.0096 (7)	0.0015 (7)
C3	0.0601 (11)	0.0542 (10)	0.0464 (9)	−0.0064 (8)	0.0015 (8)	−0.0035 (8)
C4	0.0642 (11)	0.0501 (10)	0.0412 (9)	0.0023 (9)	0.0109 (8)	0.0001 (7)
C5	0.0597 (10)	0.0585 (11)	0.0519 (10)	−0.0062 (9)	0.0217 (8)	−0.0006 (8)
C6	0.0501 (9)	0.0482 (9)	0.0512 (9)	−0.0069 (8)	0.0115 (7)	−0.0013 (7)
C7	0.1133 (17)	0.0747 (14)	0.0520 (11)	−0.0059 (14)	0.0008 (11)	−0.0156 (10)
C8	0.0411 (8)	0.0418 (9)	0.0449 (8)	−0.0003 (7)	0.0058 (7)	0.0002 (7)
C9	0.0356 (7)	0.0365 (8)	0.0369 (8)	0.0022 (6)	0.0015 (6)	0.0018 (6)
C10	0.0359 (7)	0.0355 (8)	0.0363 (7)	−0.0006 (6)	0.0051 (6)	0.0011 (6)
C11	0.0320 (7)	0.0495 (9)	0.0438 (8)	0.0056 (7)	0.0050 (6)	−0.0003 (7)
C12	0.0364 (8)	0.0616 (11)	0.0401 (8)	0.0057 (7)	−0.0030 (6)	−0.0039 (7)
C13	0.0401 (8)	0.0411 (8)	0.0360 (8)	0.0000 (7)	0.0059 (6)	0.0005 (6)
C14	0.0319 (7)	0.0442 (9)	0.0480 (9)	0.0034 (6)	0.0056 (6)	−0.0051 (7)
C15	0.0339 (8)	0.0477 (9)	0.0449 (8)	0.0021 (7)	−0.0019 (6)	−0.0039 (7)

Geometric parameters (Å, º) top

N1—C8	1.2758 (18)	C5—H5	0.93
N1—N2	1.3850 (16)	C6—H6	0.93
N2—C9	1.3408 (18)	C7—H7A	0.96
N2—H2A	0.901 (9)	C7—H7B	0.96
O1—C4	1.3610 (19)	C7—H7C	0.96
O1—C7	1.418 (2)	C8—H8	0.93
O2—C9	1.2431 (17)	C9—C10	1.4822 (19)
O3—C13	1.3554 (17)	C10—C11	1.3841 (19)
O3—H3	0.82	C10—C15	1.3868 (19)
C1—C2	1.385 (2)	C11—C12	1.3797 (19)
C1—C6	1.393 (2)	C11—H11	0.93
C1—C8	1.457 (2)	C12—C13	1.386 (2)
C2—C3	1.370 (2)	C12—H12	0.93
C2—H2	0.93	C13—C14	1.386 (2)
C3—C4	1.388 (2)	C14—C15	1.375 (2)
C3—H3A	0.93	C14—H14	0.93
C4—C5	1.385 (2)	C15—H15	0.93
C5—C6	1.375 (2)

C8—N1—N2	114.89 (13)	O1—C7—H7C	109.5
C9—N2—N1	118.86 (13)	H7A—C7—H7C	109.5
C9—N2—H2A	123.0 (12)	H7B—C7—H7C	109.5
N1—N2—H2A	117.5 (12)	N1—C8—C1	120.25 (14)
C4—O1—C7	117.85 (15)	N1—C8—H8	119.9
C13—O3—H3	109.5	C1—C8—H8	119.9
C2—C1—C6	118.11 (14)	O2—C9—N2	122.26 (13)
C2—C1—C8	121.81 (13)	O2—C9—C10	121.50 (12)
C6—C1—C8	120.08 (14)	N2—C9—C10	116.22 (13)
C3—C2—C1	121.80 (15)	C11—C10—C15	118.78 (13)
C3—C2—H2	119.1	C11—C10—C9	121.54 (12)
C1—C2—H2	119.1	C15—C10—C9	119.31 (13)
C2—C3—C4	119.46 (16)	C12—C11—C10	120.58 (13)
C2—C3—H3A	120.3	C12—C11—H11	119.7
C4—C3—H3A	120.3	C10—C11—H11	119.7
O1—C4—C5	116.26 (15)	C11—C12—C13	120.21 (13)
O1—C4—C3	124.07 (16)	C11—C12—H12	119.9
C5—C4—C3	119.67 (15)	C13—C12—H12	119.9
C6—C5—C4	120.22 (15)	O3—C13—C14	122.91 (13)
C6—C5—H5	119.9	O3—C13—C12	117.64 (13)
C4—C5—H5	119.9	C14—C13—C12	119.44 (13)
C5—C6—C1	120.67 (16)	C15—C14—C13	119.94 (13)
C5—C6—H6	119.7	C15—C14—H14	120.0
C1—C6—H6	119.7	C13—C14—H14	120.0
O1—C7—H7A	109.5	C14—C15—C10	121.01 (13)
O1—C7—H7B	109.5	C14—C15—H15	119.5
H7A—C7—H7B	109.5	C10—C15—H15	119.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.82	1.91	2.7271 (15)	171
N2—H2A···O2ⁱⁱ	0.90 (1)	2.12 (1)	3.0216 (17)	173 (2)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+3/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₃
M_r	270.28
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	11.947 (2), 7.555 (1), 29.452 (2)
V (Å³)	2658.3 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.20 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.981, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	15205, 2897, 2030
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.103, 1.04
No. of reflections	2897
No. of parameters	187
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)	0.18, −0.15

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
O3—H3···O2ⁱ	0.82	1.91	2.7271 (15)	171
N2—H2A···O2ⁱⁱ	0.90 (1)	2.12 (1)	3.0216 (17)	173 (2)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+3/2, y+1/2, z.

Acknowledgements

The present study was supported by the Natural Science Foundation of Huaihai Institute of Technology (Z2008022).

References

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