2-Hydr­oxy-N′-[(1E,2E)-3-phenyl­prop-2-enyl­idene]benzohydrazide

Ji, N.-N.; Shi, Z.-Q.

doi:10.1107/S1600536808028481

organic compounds

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Volume 64| Part 10| October 2008| Page o1918

doi:10.1107/S1600536808028481

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2-Hydroxy-N′-[(1E,2E)-3-phenylprop-2-enylidene]benzohydrazide

Ning-Ning Ji ^a ^* and Zhi-Qiang Shi ^b

^aDepartment of Chemistry, Taishan University, 271021 Taian, Shandong, People's Republic of China, and ^bDepartment of Materials Science and Chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China
^*Correspondence e-mail: jiningning16@163.com

(Received 26 August 2008; accepted 5 September 2008; online 13 September 2008)

In molecule of the title compound, C₁₆H₁₄N₂O₂, the two aromatic rings form a dihedral angle of 6.93 (3)° and an intramolecular N—H⋯O hydrogen bond occurs. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules into zigzag chains running in the [10 $[\overline{1}]$ ] direction.

Related literature

For the coordination chemistry of Schiff bases, see: Garnovskii et al. (1993 ); Musie et al. (2001 ); Paul et al. (2002 ); Shi et al. (2007 ). For Schiff bases and biological systems, see: Anderson et al. (1997 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₄N₂O₂
M_r = 266.29
Monoclinic, P 2₁ /n
a = 4.8892 (6) Å
b = 26.563 (3) Å
c = 10.7367 (13) Å
β = 102.305 (2)°
V = 1362.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.987, T_max = 0.991
7141 measured reflections
2395 independent reflections
1354 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.123
S = 1.05
2395 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	1.97	2.6348 (19)	133
O1—H1⋯O2ⁱ	0.82	2.10	2.804 (3)	144
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 global, I. DOI: 10.1107/S1600536808028481/cv2440sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808028481/cv2440Isup2.hkl

checkCIF report

Comment top

In recent years, a number of Schiff-bases have been investigated in terms of their coordination chemistry (Garnovskii et al., 1993; Musie et al., 2001; Paul et al., 2002; Shi et al., 2007;) and biological systems (Anderson et al., 1997). In order to search for new Schiff-bases with higher bioactivity, the title compound, (I), was synthesized and its crystal structure determined.

In (I) (Fig. 1), the bond lengths and angles are in good agreement with the expected values (Allen et al., 1987). The intramolecular N—H···O hydrogen bond (Table 1) influences the molecular conformation. In the crystal, the molecules are linked into infinite chains along direction [10-1] by O—H···O hydrogen bonds (Table 1).

Related literature top

For the coordination chemistry of Schiff bases, see: Garnovskii et al. (1993); Musie et al. (2001); Paul et al. (2002); Shi et al. (2007); For Schiff bases and biological systems, see: Anderson et al. (1997). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was synthesized by the reaction of 2-Hydroxy-benzoic acid hydrazide(1 mmol, 152.2 mg) with 3-Phenyl-propenal (1 mmol, 132.2 mg) in ethanol(20 ml) under reflux conditions (348 K) for 6 h. The solvent was removed and the solid product recrystallized from tetrahydrofuran. After six days colorless crystals suitable for X-ray diffraction study were obtained. Yield, 226.3 mg, 85%. m.p. 239–241 K. Analysis calculated for C₁₆H₁₄N₂O₂: C 72.16, H 5.30, N 10.52%; found: C 71.73, H 5.34, N 10.48%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (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. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.

2-Hydroxy-N'-[(1E,2E)-3-phenylprop-2- enylidene]benzohydrazide top

Crystal data top

C₁₆H₁₄N₂O₂	F(000) = 560
M_r = 266.29	D_x = 1.298 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 932 reflections
a = 4.8892 (6) Å	θ = 3.6–21.4°
b = 26.563 (3) Å	µ = 0.09 mm⁻¹
c = 10.7367 (13) Å	T = 295 K
β = 102.305 (2)°	Block, colourless
V = 1362.4 (3) Å³	0.15 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2395 independent reflections
Radiation source: fine-focus sealed tube	1354 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
T_min = 0.987, T_max = 0.991	k = −21→31
7141 measured reflections	l = −12→12

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)] = 0.047	H-atom parameters constrained
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0505P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2395 reflections	Δρ_max = 0.14 e Å⁻³
183 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (2)

Crystal data top

C₁₆H₁₄N₂O₂	V = 1362.4 (3) Å³
M_r = 266.29	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.8892 (6) Å	µ = 0.09 mm⁻¹
b = 26.563 (3) Å	T = 295 K
c = 10.7367 (13) Å	0.15 × 0.12 × 0.10 mm
β = 102.305 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2395 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1354 reflections with I > 2σ(I)
T_min = 0.987, T_max = 0.991	R_int = 0.038
7141 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.05	Δρ_max = 0.14 e Å⁻³
2395 reflections	Δρ_min = −0.13 e Å⁻³
183 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
O1	0.5440 (4)	0.26610 (6)	0.08347 (14)	0.0702 (5)
H1	0.6201	0.2633	0.0227	0.105*
O2	0.4213 (4)	0.27755 (6)	0.45173 (13)	0.0687 (5)
N1	0.2766 (4)	0.24015 (6)	0.26236 (15)	0.0508 (5)
H1A	0.2861	0.2378	0.1835	0.061*
N2	0.1041 (4)	0.20892 (7)	0.31262 (16)	0.0513 (5)
C1	0.6656 (4)	0.30391 (8)	0.15959 (19)	0.0483 (6)
C2	0.6118 (4)	0.30864 (8)	0.28157 (18)	0.0450 (5)
C3	0.7379 (5)	0.34777 (9)	0.3569 (2)	0.0634 (7)
H3	0.7048	0.3513	0.4386	0.076*
C4	0.9102 (6)	0.38164 (9)	0.3154 (2)	0.0736 (8)
H4	0.9898	0.4080	0.3676	0.088*
C5	0.9638 (5)	0.37611 (9)	0.1959 (2)	0.0662 (7)
H5	1.0826	0.3986	0.1674	0.079*
C6	0.8438 (5)	0.33774 (9)	0.1184 (2)	0.0606 (7)
H6	0.8818	0.3343	0.0375	0.073*
C7	0.4304 (5)	0.27445 (8)	0.33872 (19)	0.0476 (6)
C8	−0.0380 (5)	0.17709 (8)	0.2358 (2)	0.0529 (6)
H8	−0.0220	0.1766	0.1510	0.064*
C9	−0.2215 (5)	0.14220 (8)	0.2788 (2)	0.0530 (6)
H9	−0.2416	0.1442	0.3628	0.064*
C10	−0.3630 (5)	0.10743 (9)	0.2044 (2)	0.0576 (6)
H10	−0.3419	0.1072	0.1203	0.069*
C11	−0.5490 (5)	0.06929 (8)	0.2383 (2)	0.0529 (6)
C12	−0.6805 (5)	0.03509 (10)	0.1480 (2)	0.0739 (8)
H12	−0.6499	0.0369	0.0655	0.089*
C13	−0.8563 (6)	−0.00161 (11)	0.1777 (3)	0.0842 (9)
H13	−0.9404	−0.0244	0.1156	0.101*
C14	−0.9071 (6)	−0.00457 (10)	0.2973 (3)	0.0761 (8)
H14	−1.0287	−0.0288	0.3169	0.091*
C15	−0.7772 (6)	0.02847 (10)	0.3879 (3)	0.0807 (8)
H15	−0.8084	0.0264	0.4702	0.097*
C16	−0.6002 (5)	0.06496 (9)	0.3590 (2)	0.0670 (7)
H16	−0.5137	0.0871	0.4223	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0858 (13)	0.0893 (13)	0.0482 (9)	−0.0339 (10)	0.0428 (9)	−0.0229 (9)
O2	0.0900 (14)	0.0857 (12)	0.0392 (9)	−0.0137 (9)	0.0337 (8)	−0.0060 (8)
N1	0.0615 (13)	0.0615 (12)	0.0363 (9)	−0.0068 (10)	0.0257 (9)	0.0017 (9)
N2	0.0587 (13)	0.0596 (12)	0.0424 (10)	−0.0030 (10)	0.0263 (9)	0.0069 (9)
C1	0.0531 (15)	0.0568 (14)	0.0384 (12)	−0.0055 (11)	0.0174 (10)	−0.0034 (10)
C2	0.0509 (15)	0.0505 (13)	0.0366 (11)	0.0016 (11)	0.0158 (10)	0.0003 (10)
C3	0.083 (2)	0.0703 (17)	0.0416 (13)	−0.0132 (14)	0.0247 (12)	−0.0088 (12)
C4	0.097 (2)	0.0700 (18)	0.0568 (16)	−0.0233 (15)	0.0219 (15)	−0.0121 (13)
C5	0.0740 (19)	0.0696 (17)	0.0575 (15)	−0.0225 (14)	0.0192 (14)	0.0020 (13)
C6	0.0701 (18)	0.0765 (17)	0.0412 (12)	−0.0134 (13)	0.0252 (12)	0.0026 (12)
C7	0.0552 (15)	0.0547 (14)	0.0383 (12)	0.0047 (11)	0.0218 (11)	0.0002 (11)
C8	0.0614 (17)	0.0631 (15)	0.0377 (12)	−0.0015 (12)	0.0183 (11)	0.0042 (11)
C9	0.0580 (16)	0.0613 (15)	0.0440 (13)	−0.0030 (12)	0.0205 (11)	0.0068 (11)
C10	0.0613 (17)	0.0687 (16)	0.0444 (13)	−0.0007 (13)	0.0151 (12)	0.0044 (12)
C11	0.0528 (16)	0.0563 (15)	0.0501 (14)	0.0024 (12)	0.0118 (11)	0.0029 (12)
C12	0.079 (2)	0.086 (2)	0.0571 (16)	−0.0149 (16)	0.0147 (14)	−0.0071 (14)
C13	0.082 (2)	0.082 (2)	0.085 (2)	−0.0215 (16)	0.0086 (17)	−0.0090 (16)
C14	0.0696 (19)	0.0665 (19)	0.093 (2)	−0.0088 (14)	0.0189 (16)	0.0139 (16)
C15	0.092 (2)	0.082 (2)	0.0768 (18)	−0.0177 (16)	0.0376 (17)	0.0056 (16)
C16	0.076 (2)	0.0684 (17)	0.0609 (16)	−0.0142 (13)	0.0244 (14)	−0.0028 (12)

Geometric parameters (Å, º) top

O1—C1	1.350 (2)	C8—C9	1.433 (3)
O1—H1	0.8200	C8—H8	0.9300
O2—C7	1.226 (2)	C9—C10	1.317 (3)
N1—C7	1.344 (2)	C9—H9	0.9300
N1—N2	1.373 (2)	C10—C11	1.458 (3)
N1—H1A	0.8600	C10—H10	0.9300
N2—C8	1.278 (2)	C11—C16	1.376 (3)
C1—C6	1.388 (3)	C11—C12	1.383 (3)
C1—C2	1.395 (3)	C12—C13	1.381 (3)
C2—C3	1.379 (3)	C12—H12	0.9300
C2—C7	1.490 (3)	C13—C14	1.361 (3)
C3—C4	1.370 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.362 (3)
C4—C5	1.371 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.378 (3)
C5—C6	1.366 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300

C1—O1—H1	109.5	N2—C8—H8	119.6
C7—N1—N2	118.73 (17)	C9—C8—H8	119.6
C7—N1—H1A	120.6	C10—C9—C8	122.9 (2)
N2—N1—H1A	120.6	C10—C9—H9	118.6
C8—N2—N1	116.17 (17)	C8—C9—H9	118.6
O1—C1—C6	120.93 (18)	C9—C10—C11	127.6 (2)
O1—C1—C2	119.23 (18)	C9—C10—H10	116.2
C6—C1—C2	119.8 (2)	C11—C10—H10	116.2
C3—C2—C1	117.9 (2)	C16—C11—C12	117.0 (2)
C3—C2—C7	116.66 (18)	C16—C11—C10	122.8 (2)
C1—C2—C7	125.41 (19)	C12—C11—C10	120.2 (2)
C4—C3—C2	122.2 (2)	C13—C12—C11	121.4 (2)
C4—C3—H3	118.9	C13—C12—H12	119.3
C2—C3—H3	118.9	C11—C12—H12	119.3
C3—C4—C5	119.2 (2)	C14—C13—C12	120.4 (3)
C3—C4—H4	120.4	C14—C13—H13	119.8
C5—C4—H4	120.4	C12—C13—H13	119.8
C6—C5—C4	120.5 (2)	C13—C14—C15	119.0 (3)
C6—C5—H5	119.8	C13—C14—H14	120.5
C4—C5—H5	119.8	C15—C14—H14	120.5
C5—C6—C1	120.4 (2)	C14—C15—C16	120.8 (3)
C5—C6—H6	119.8	C14—C15—H15	119.6
C1—C6—H6	119.8	C16—C15—H15	119.6
O2—C7—N1	121.0 (2)	C11—C16—C15	121.3 (2)
O2—C7—C2	121.1 (2)	C11—C16—H16	119.3
N1—C7—C2	117.84 (17)	C15—C16—H16	119.3
N2—C8—C9	120.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.97	2.6348 (19)	133
O1—H1···O2ⁱ	0.82	2.10	2.804 (3)	144
O1—H1···N2ⁱ	0.82	2.36	3.057 (3)	144

Symmetry code: (i) x+1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂O₂
M_r	266.29
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	4.8892 (6), 26.563 (3), 10.7367 (13)
β (°)	102.305 (2)
V (Å³)	1362.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.15 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.987, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	7141, 2395, 1354
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.124, 1.05
No. of reflections	2395
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.13

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—H1A···O1	0.86	1.97	2.6348 (19)	133.0
O1—H1···O2ⁱ	0.820	2.099	2.804 (3)	143.92

Symmetry code: (i) x+1/2, −y+1/2, z−1/2.

Acknowledgements

This project was supported by the Postgraduate Foundation of Taishan University (grant No. Y06-2-08).

References

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