(E)-N′-[1-(2-Hydroxy­phen­yl)ethyl­idene]-3-methoxy­benzohydrazide

Li, C.-M.; Ban, H.-Y.

doi:10.1107/S1600536809010228

organic compounds

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Volume 65| Part 4| April 2009| Page o876

doi:10.1107/S1600536809010228

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(E)-N′-[1-(2-Hydroxyphenyl)ethylidene]-3-methoxybenzohydrazide

Cong-Ming Li ^a ^* and Hong-Yan Ban ^b

^aCollege of Science, Shenyang University, Shenyang 110044, People's Republic of China, and ^bSchool of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, People's Republic of China
^*Correspondence e-mail: hongyan_ban@163.com

(Received 12 March 2009; accepted 19 March 2009; online 28 March 2009)

In the title compound, C₁₆H₁₆N₂O₃, the benzohydrazide group is not planar and the molecule exists in a trans configuration with respect to the methylidene unit. The dihedral angle between the two substituted benzene rings is 26.9 (2)°. In the crystal structure, the molecular packing is stabilized by intramolecular O—H⋯N and intermolecular N—H⋯O hydrogen bonds. The intermolecular hydrogen bonding forms chains parallel to the b axis.

Related literature

For the biological activities of hydrazones, see: Zhong et al. (2007 ); Raj et al. (2007 ); Jimenez-Pulido et al. (2008 ). For related structures, see: Ban & Li (2008a ,b ); Yehye et al. (2008 ); Fun et al. (2008a ,b ); Yang et al. (2008 ); Ejsmont et al. (2008 ).

Experimental

Crystal data

C₁₆H₁₆N₂O₃
M_r = 284.31
Orthorhombic, P b c a
a = 12.932 (2) Å
b = 8.756 (2) Å
c = 25.784 (3) Å
V = 2919.7 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.27 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.976, T_max = 0.982
22735 measured reflections
3180 independent reflections
2023 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.145
S = 1.01
3180 reflections
196 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 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
N2—H2⋯O2ⁱ	0.897 (10)	2.010 (11)	2.894 (2)	168 (2)
O1—H1⋯N1	0.82	1.82	2.534 (2)	145
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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/S1600536809010228/bx2198sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010228/bx2198Isup2.hkl

checkCIF report

Comment top

Hydrazones derived from the condensation of aldehydes with hydrazides have been demonstrated to possess excellent biological activities (Zhong et al., 2007; Raj et al., 2007; Jimenez-Pulido et al., 2008). Due to the easy synthesis of such compounds, a great deal of hydrazones have been synthesized and structurally characterized (Yehye et al., 2008; Fun et al., 2008a,b; Yang et al., 2008; Ejsmont et al., 2008). Recently, we have reported two hydrazones (Ban & Li, 2008a,b). In this paper, we report herein the crystal structure of the title compound, (I). In the structure of (I), Fig. 1, the molecule exists in a trans configuration with respect to the methylidene unit. The dihedral angle between the two substituted benzene rings is 26.9 (2)°. In the 3-methoxyphenyl unit, the methoxy group is nearly coplanar with the mean plane of the C10–C15 ring, with the C16 atom deviates from the plane by 0.024 (2) Å. The torsion angle of C7-N1-N2-C9 is 8.0 (3)°. In the crystal structure the molecular packing is stabilized by intramolecular O-H···N and intermolecular N—H···O hydrogen bonds, Table 1. The intermolecular hydrogen bond form chains parallel to the b axis, Fig. 2.

Related literature top

For the biological activities of hydrazones, see: Zhong et al. (2007); Raj et al. (2007); Jimenez-Pulido et al. (2008). For related structures, see: Ban & Li (2008a,b); Yehye et al. (2008); Fun et al. (2008a,b); Yang et al. (2008); Ejsmont et al. (2008).

Experimental top

The compound was prepared by refluxing 1-(2-hydroxyphenyl)ethanone (1.0 mol, 0136 g ) with 3-methoxybenzohydrazide (1.0 mol), 0166 g) in methanol (100 ml). Excess methanol was removed from the mixture by distillation. The colorless solid product was filtered, and washed three times with methanol. Colorless block crystals of the title compound were obtained from a methanol solution by slow evaporation 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 (I), showing 30% probability displacement ellipsoids for the non-hydrogen atoms. Intramolecular O—H···N is shown as a dashed line.
	Fig. 2. The packing diagram of (I), viewed along the a axis. Hydrogen bonds are shown as dashed lines.

(E)-N'-[1-(2-Hydroxyphenyl)ethylidene]-3-methoxybenzohydrazide top

Crystal data top

C₁₆H₁₆N₂O₃	F(000) = 1200
M_r = 284.31	D_x = 1.294 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2030 reflections
a = 12.932 (2) Å	θ = 2.3–24.6°
b = 8.756 (2) Å	µ = 0.09 mm⁻¹
c = 25.784 (3) Å	T = 298 K
V = 2919.7 (9) Å³	Block, colourless
Z = 8	0.27 × 0.23 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3180 independent reflections
Radiation source: fine-focus sealed tube	2023 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
ω scans	θ_max = 27.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.976, T_max = 0.982	k = −11→11
22735 measured reflections	l = −32→32

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0537P)² + 0.9645P] where P = (F_o² + 2F_c²)/3
3180 reflections	(Δ/σ)_max < 0.001
196 parameters	Δρ_max = 0.17 e Å⁻³
1 restraint	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O₃	V = 2919.7 (9) Å³
M_r = 284.31	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.932 (2) Å	µ = 0.09 mm⁻¹
b = 8.756 (2) Å	T = 298 K
c = 25.784 (3) Å	0.27 × 0.23 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3180 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2023 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.982	R_int = 0.060
22735 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	1 restraint
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.17 e Å⁻³
3180 reflections	Δρ_min = −0.13 e Å⁻³
196 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
O1	0.36951 (13)	−0.23812 (18)	0.55231 (7)	0.0649 (5)
H1	0.3402	−0.1716	0.5692	0.097*
O2	0.16810 (12)	−0.08166 (16)	0.63341 (7)	0.0637 (5)
O3	−0.13883 (13)	0.2606 (3)	0.68697 (8)	0.0904 (7)
N1	0.35910 (13)	−0.00001 (18)	0.60790 (6)	0.0449 (4)
N2	0.29750 (13)	0.09206 (19)	0.63821 (7)	0.0455 (4)
C1	0.51395 (16)	−0.0694 (2)	0.56716 (8)	0.0464 (5)
C2	0.46801 (19)	−0.1972 (2)	0.54406 (8)	0.0531 (6)
C3	0.5262 (2)	−0.2881 (3)	0.51064 (10)	0.0698 (7)
H3	0.4956	−0.3729	0.4953	0.084*
C4	0.6267 (3)	−0.2557 (3)	0.49994 (11)	0.0783 (9)
H4	0.6643	−0.3189	0.4779	0.094*
C5	0.6727 (2)	−0.1300 (3)	0.52166 (10)	0.0726 (8)
H5	0.7413	−0.1067	0.5141	0.087*
C6	0.61702 (17)	−0.0388 (3)	0.55467 (9)	0.0605 (6)
H6	0.6489	0.0462	0.5692	0.073*
C7	0.45502 (16)	0.0315 (2)	0.60247 (8)	0.0460 (5)
C8	0.50836 (18)	0.1605 (3)	0.62968 (11)	0.0736 (8)
H8A	0.5115	0.2475	0.6071	0.110*
H8B	0.5772	0.1299	0.6389	0.110*
H8C	0.4706	0.1867	0.6605	0.110*
C9	0.20029 (16)	0.0434 (2)	0.64786 (8)	0.0453 (5)
C10	0.13506 (15)	0.1510 (2)	0.67804 (7)	0.0416 (5)
C11	0.02940 (15)	0.1511 (2)	0.66810 (8)	0.0472 (5)
H11	0.0020	0.0846	0.6436	0.057*
C12	−0.03443 (18)	0.2490 (3)	0.69451 (9)	0.0587 (6)
C13	0.0058 (2)	0.3454 (3)	0.73150 (10)	0.0744 (8)
H13	−0.0375	0.4117	0.7494	0.089*
C14	0.1094 (2)	0.3437 (3)	0.74187 (10)	0.0741 (8)
H14	0.1361	0.4087	0.7671	0.089*
C15	0.17528 (17)	0.2464 (3)	0.71537 (9)	0.0551 (6)
H15	0.2457	0.2454	0.7227	0.066*
C16	−0.1850 (2)	0.1657 (4)	0.64939 (12)	0.0932 (10)
H16A	−0.1543	0.1853	0.6162	0.140*
H16B	−0.2578	0.1865	0.6478	0.140*
H16C	−0.1743	0.0607	0.6586	0.140*
H2	0.3118 (19)	0.1919 (13)	0.6414 (10)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0719 (12)	0.0497 (10)	0.0731 (12)	−0.0087 (9)	−0.0043 (9)	−0.0107 (8)
O2	0.0519 (9)	0.0352 (8)	0.1039 (13)	−0.0034 (7)	−0.0095 (9)	−0.0069 (8)
O3	0.0454 (10)	0.1393 (19)	0.0865 (14)	0.0128 (11)	0.0099 (10)	−0.0058 (13)
N1	0.0432 (10)	0.0389 (9)	0.0524 (10)	0.0035 (8)	−0.0032 (8)	−0.0017 (8)
N2	0.0426 (10)	0.0339 (9)	0.0602 (11)	0.0017 (8)	0.0002 (8)	−0.0049 (9)
C1	0.0512 (13)	0.0411 (12)	0.0468 (12)	0.0051 (10)	−0.0031 (10)	0.0027 (9)
C2	0.0687 (16)	0.0415 (13)	0.0490 (13)	0.0059 (11)	−0.0025 (11)	0.0042 (10)
C3	0.104 (2)	0.0451 (15)	0.0607 (16)	0.0093 (14)	0.0061 (15)	−0.0058 (12)
C4	0.101 (2)	0.0675 (18)	0.0664 (17)	0.0287 (17)	0.0235 (16)	0.0042 (14)
C5	0.0695 (17)	0.0764 (19)	0.0720 (17)	0.0163 (15)	0.0202 (14)	0.0064 (15)
C6	0.0561 (15)	0.0587 (15)	0.0666 (15)	0.0054 (12)	0.0031 (12)	0.0024 (12)
C7	0.0440 (12)	0.0407 (11)	0.0534 (13)	0.0070 (9)	−0.0078 (10)	−0.0012 (10)
C8	0.0466 (14)	0.0697 (17)	0.105 (2)	0.0040 (12)	−0.0096 (14)	−0.0346 (16)
C9	0.0429 (12)	0.0363 (11)	0.0567 (13)	0.0008 (9)	−0.0096 (10)	0.0052 (10)
C10	0.0436 (11)	0.0387 (11)	0.0427 (11)	−0.0043 (9)	−0.0015 (9)	0.0073 (9)
C11	0.0445 (12)	0.0505 (13)	0.0466 (12)	−0.0060 (10)	0.0016 (10)	0.0068 (10)
C12	0.0467 (14)	0.0763 (17)	0.0531 (14)	0.0014 (12)	0.0097 (11)	0.0084 (13)
C13	0.0687 (18)	0.094 (2)	0.0608 (16)	0.0095 (15)	0.0184 (14)	−0.0177 (15)
C14	0.0771 (19)	0.092 (2)	0.0529 (15)	−0.0094 (16)	0.0051 (13)	−0.0249 (14)
C15	0.0464 (12)	0.0690 (15)	0.0498 (13)	−0.0057 (11)	−0.0005 (10)	−0.0029 (12)
C16	0.0430 (15)	0.140 (3)	0.097 (2)	−0.0071 (16)	−0.0068 (15)	0.012 (2)

Geometric parameters (Å, º) top

O1—C2	1.340 (3)	C6—H6	0.9300
O1—H1	0.8200	C7—C8	1.498 (3)
O2—C9	1.229 (2)	C8—H8A	0.9600
O3—C12	1.368 (3)	C8—H8B	0.9600
O3—C16	1.409 (4)	C8—H8C	0.9600
N1—C7	1.278 (2)	C9—C10	1.485 (3)
N1—N2	1.377 (2)	C10—C15	1.376 (3)
N2—C9	1.351 (3)	C10—C11	1.390 (3)
N2—H2	0.897 (10)	C11—C12	1.371 (3)
C1—C6	1.397 (3)	C11—H11	0.9300
C1—C2	1.401 (3)	C12—C13	1.376 (3)
C1—C7	1.480 (3)	C13—C14	1.367 (4)
C2—C3	1.394 (3)	C13—H13	0.9300
C3—C4	1.358 (4)	C14—C15	1.385 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.371 (4)	C15—H15	0.9300
C4—H4	0.9300	C16—H16A	0.9600
C5—C6	1.372 (3)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600

C2—O1—H1	109.5	C7—C8—H8C	109.5
C12—O3—C16	118.2 (2)	H8A—C8—H8C	109.5
C7—N1—N2	119.81 (17)	H8B—C8—H8C	109.5
C9—N2—N1	117.28 (17)	O2—C9—N2	122.7 (2)
C9—N2—H2	118.8 (16)	O2—C9—C10	122.1 (2)
N1—N2—H2	120.2 (17)	N2—C9—C10	115.14 (18)
C6—C1—C2	117.4 (2)	C15—C10—C11	120.0 (2)
C6—C1—C7	121.3 (2)	C15—C10—C9	122.46 (19)
C2—C1—C7	121.4 (2)	C11—C10—C9	117.50 (18)
O1—C2—C3	117.3 (2)	C12—C11—C10	120.0 (2)
O1—C2—C1	123.3 (2)	C12—C11—H11	120.0
C3—C2—C1	119.3 (2)	C10—C11—H11	120.0
C4—C3—C2	121.6 (3)	O3—C12—C11	124.7 (2)
C4—C3—H3	119.2	O3—C12—C13	115.2 (2)
C2—C3—H3	119.2	C11—C12—C13	120.0 (2)
C3—C4—C5	120.0 (3)	C14—C13—C12	120.0 (2)
C3—C4—H4	120.0	C14—C13—H13	120.0
C5—C4—H4	120.0	C12—C13—H13	120.0
C4—C5—C6	119.5 (3)	C13—C14—C15	120.9 (2)
C4—C5—H5	120.2	C13—C14—H14	119.6
C6—C5—H5	120.2	C15—C14—H14	119.6
C5—C6—C1	122.2 (2)	C10—C15—C14	119.1 (2)
C5—C6—H6	118.9	C10—C15—H15	120.5
C1—C6—H6	118.9	C14—C15—H15	120.5
N1—C7—C1	115.99 (19)	O3—C16—H16A	109.5
N1—C7—C8	123.94 (19)	O3—C16—H16B	109.5
C1—C7—C8	120.07 (19)	H16A—C16—H16B	109.5
C7—C8—H8A	109.5	O3—C16—H16C	109.5
C7—C8—H8B	109.5	H16A—C16—H16C	109.5
H8A—C8—H8B	109.5	H16B—C16—H16C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.90 (1)	2.01 (1)	2.894 (2)	168 (2)
O1—H1···N1	0.82	1.82	2.534 (2)	145

Symmetry code: (i) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₃
M_r	284.31
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	12.932 (2), 8.756 (2), 25.784 (3)
V (Å³)	2919.7 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.27 × 0.23 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.976, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	22735, 3180, 2023
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.145, 1.01
No. of reflections	3180
No. of parameters	196
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)	0.17, −0.13

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···O2ⁱ	0.897 (10)	2.010 (11)	2.894 (2)	168 (2)
O1—H1···N1	0.82	1.82	2.534 (2)	144.7

Symmetry code: (i) −x+1/2, y+1/2, z.

Acknowledgements

Financial support of this work was provided by the Research Foundation of Liaoning Province (grant No. 2008470).

References

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