N′-[(1E)-1-(2-Hydr­oxy-5-methyl­phenyl)­ethyl­idene]-4-methoxy­benzohydrazide

Chang, J.-G.; Ji, C.-Y.

doi:10.1107/S1600536807027882

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N′-[(1E)-1-(2-Hydroxy-5-methylphenyl)ethylidene]-4-methoxybenzohydrazide

J.-G. Chang and C.-Y. Ji

The title compound, C₁₇H₁₈N₂O₃, displays a trans conformation with respect to the C=N double bond. The crystal structure is stabilized by intramolecular O—H

N and intermolecular N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027882/fj2040sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027882/fj2040Isup2.hkl Contains datablock I

CCDC reference: 654955

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C)= 0.004 Å
R factor = 0.051
wR factor = 0.178
Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Comment top

The chemistry of aroylhydrazones continues to attract much attention due to their coordination ability to metal ions (Singh et al., 1982; Salem, 1998) and their biological activity (Singh et al., 1982; Carcelli et al., 1995). As an extension of work on the structural characterization of aroylhydrazone derivatives, the title compound (I) was synthesized and its crystal structure is reported here.

The title molecule displays a trans conformation with respect to the C8=N1 double bond (Fig. 1). The dihedral angle between the two benzene rings is 4.66 (16)°. The crystal structure is stabilized by intramolecular O—H···N and intermolecular N—H···O hydrogen bonds (Table 1. and Fig. 2).

Related literature top

For related literature, see: Carcelli et al. (1995); Salem (1998); Singh et al. (1982).

Experimental top

4-methoxybenzohydrazide (0.01 mol,1.66 g) was dissolved in anhydrous ethanol (50 ml), and 1-(2-hydroxy-5-methylphenyl)ethanone (0.01 mol, 1.50 g) was added. The reaction mixture was refluxed for 4 h with stirring, then the resulting precipitate was collected by filtration, washed several times with ethanol and dried in vacuo (yield 81%). The compound (1.0 mmol,0.29 g) was dissolved in dimethylformamide (15 ml) and kept at room temperature for 20 d to obtain colourless single crystals suitable for X-ray diffraction.

Structure description top

For related literature, see: Carcelli et al. (1995); Salem (1998); Singh et al. (1982).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of compound (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of (I), viewed along the c axis. Dashed lines show intra-and intermolecular hydrogen bonds.

N'-[(1E)-1-(2-Hydroxy-5-methylphenyl)ethylidene]-4-methoxybenzohydrazide top

Crystal data top

C₁₇H₁₈N₂O₃	F(000) = 632
M_r = 298.33	D_x = 1.318 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1229 reflections
a = 15.2171 (13) Å	θ = 2.4–21.3°
b = 4.9253 (4) Å	µ = 0.09 mm⁻¹
c = 20.0906 (16) Å	T = 273 K
β = 93.021 (3)°	Plate, colourless
V = 1503.7 (2) Å³	0.35 × 0.24 × 0.13 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	2641 independent reflections
Radiation source: fine-focus sealed tube	1598 reflections with I > 2s˘I)
Graphite monochromator	R_int = 0.072
φ and ω scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −17→18
T_min = 0.971, T_max = 0.992	k = −5→5
16192 measured reflections	l = −23→23

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)] = 0.051	H-atom parameters constrained
wR(F²) = 0.178	w = 1/[σ²(F_o²) + (0.105P)² + 0.0006P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.003
2641 reflections	Δρ_max = 0.21 e Å⁻³
204 parameters	Δρ_min = −0.21 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: 0.007 (2)

Crystal data top

C₁₇H₁₈N₂O₃	V = 1503.7 (2) Å³
M_r = 298.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.2171 (13) Å	µ = 0.09 mm⁻¹
b = 4.9253 (4) Å	T = 273 K
c = 20.0906 (16) Å	0.35 × 0.24 × 0.13 mm
β = 93.021 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2641 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1598 reflections with I > 2s˘I)
T_min = 0.971, T_max = 0.992	R_int = 0.072
16192 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
2641 reflections	Δρ_min = −0.21 e Å⁻³
204 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	0.24549 (12)	−0.3586 (4)	0.14131 (10)	0.0686 (6)
H1	0.1961	−0.2985	0.1321	0.103*
O2	0.01369 (11)	−0.4028 (3)	0.09357 (9)	0.0591 (6)
O3	−0.35729 (13)	0.0552 (4)	−0.00730 (10)	0.0760 (6)
N1	0.11590 (13)	−0.0443 (4)	0.15312 (10)	0.0479 (6)
N2	0.03244 (13)	0.0274 (4)	0.12841 (9)	0.0473 (6)
H2	0.0115	0.1877	0.1338	0.057*
C1	0.28167 (17)	−0.2245 (5)	0.19477 (12)	0.0503 (7)
C2	0.23917 (16)	−0.0114 (5)	0.22697 (12)	0.0450 (6)
C3	0.28441 (17)	0.1048 (5)	0.28221 (12)	0.0528 (7)
H3	0.2571	0.2445	0.3045	0.063*
C4	0.36719 (17)	0.0243 (6)	0.30568 (13)	0.0564 (7)
C5	0.40601 (18)	−0.1847 (6)	0.27243 (15)	0.0626 (8)
H5	0.4617	−0.2442	0.2872	0.075*
C6	0.36474 (18)	−0.3072 (6)	0.21818 (15)	0.0631 (8)
H6	0.3928	−0.4477	0.1968	0.076*
C7	0.4129 (2)	0.1559 (7)	0.36580 (15)	0.0768 (9)
H7A	0.3776	0.3031	0.3807	0.115*
H7B	0.4691	0.2239	0.3541	0.115*
H7C	0.4210	0.0243	0.4008	0.115*
C8	0.15058 (16)	0.0812 (5)	0.20433 (12)	0.0444 (6)
C9	0.10478 (17)	0.3000 (6)	0.24057 (13)	0.0591 (8)
H9A	0.1290	0.4732	0.2295	0.089*
H9B	0.1128	0.2704	0.2877	0.089*
H9C	0.0431	0.2972	0.2278	0.089*
C10	−0.01451 (16)	−0.1688 (5)	0.09532 (11)	0.0437 (6)
C11	−0.10208 (16)	−0.0933 (5)	0.06576 (11)	0.0432 (6)
C12	−0.15304 (18)	0.1148 (5)	0.09037 (13)	0.0536 (7)
H12	−0.1298	0.2249	0.1246	0.064*
C13	−0.23702 (19)	0.1592 (6)	0.06474 (14)	0.0611 (8)
H13	−0.2708	0.2969	0.0821	0.073*
C14	−0.27177 (18)	−0.0003 (5)	0.01309 (13)	0.0549 (7)
C15	−0.22169 (19)	−0.2015 (6)	−0.01320 (13)	0.0588 (7)
H15	−0.2441	−0.3049	−0.0489	0.071*
C16	−0.13797 (17)	−0.2490 (5)	0.01381 (12)	0.0521 (7)
H16	−0.1048	−0.3888	−0.0033	0.062*
C17	−0.3986 (2)	−0.1216 (8)	−0.05566 (16)	0.0916 (11)
H17A	−0.3719	−0.0983	−0.0976	0.137*
H17B	−0.4601	−0.0793	−0.0608	0.137*
H17C	−0.3914	−0.3064	−0.0411	0.137*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0628 (13)	0.0653 (13)	0.0770 (13)	0.0135 (10)	−0.0026 (10)	−0.0234 (11)
O2	0.0629 (12)	0.0356 (10)	0.0775 (12)	0.0072 (9)	−0.0083 (9)	−0.0033 (9)
O3	0.0581 (13)	0.0836 (15)	0.0846 (14)	0.0056 (11)	−0.0118 (11)	0.0048 (12)
N1	0.0463 (13)	0.0395 (12)	0.0572 (12)	0.0029 (10)	−0.0036 (10)	−0.0015 (10)
N2	0.0490 (13)	0.0350 (11)	0.0575 (12)	0.0053 (10)	−0.0007 (10)	−0.0055 (10)
C1	0.0458 (15)	0.0461 (15)	0.0592 (16)	−0.0028 (13)	0.0057 (12)	−0.0021 (13)
C2	0.0452 (15)	0.0385 (14)	0.0516 (14)	−0.0014 (12)	0.0060 (12)	0.0026 (11)
C3	0.0514 (17)	0.0497 (16)	0.0578 (16)	0.0001 (13)	0.0082 (13)	−0.0013 (13)
C4	0.0458 (16)	0.0582 (18)	0.0650 (17)	−0.0068 (14)	0.0009 (13)	0.0050 (14)
C5	0.0453 (16)	0.0640 (19)	0.0783 (19)	0.0015 (14)	0.0023 (15)	0.0045 (16)
C6	0.0505 (17)	0.0578 (18)	0.0814 (19)	0.0076 (14)	0.0082 (15)	−0.0054 (16)
C7	0.063 (2)	0.092 (2)	0.0745 (19)	−0.0073 (17)	−0.0084 (16)	−0.0066 (18)
C8	0.0471 (15)	0.0366 (13)	0.0499 (14)	−0.0008 (11)	0.0063 (12)	0.0033 (11)
C9	0.0572 (17)	0.0591 (17)	0.0610 (16)	0.0086 (13)	0.0022 (13)	−0.0113 (14)
C10	0.0509 (16)	0.0337 (14)	0.0466 (13)	0.0015 (12)	0.0041 (12)	−0.0002 (11)
C11	0.0507 (15)	0.0354 (13)	0.0434 (13)	0.0020 (11)	0.0035 (12)	0.0024 (11)
C12	0.0575 (18)	0.0449 (16)	0.0580 (15)	0.0025 (13)	−0.0003 (13)	−0.0065 (13)
C13	0.0576 (18)	0.0522 (17)	0.0734 (18)	0.0142 (14)	0.0034 (15)	−0.0049 (15)
C14	0.0517 (17)	0.0560 (17)	0.0566 (16)	0.0039 (14)	−0.0011 (13)	0.0107 (14)
C15	0.068 (2)	0.0585 (17)	0.0493 (15)	0.0000 (15)	−0.0052 (14)	−0.0038 (13)
C16	0.0580 (17)	0.0470 (16)	0.0512 (15)	0.0085 (13)	0.0028 (13)	−0.0035 (12)
C17	0.069 (2)	0.121 (3)	0.081 (2)	0.000 (2)	−0.0258 (18)	0.008 (2)

Geometric parameters (Å, º) top

O1—C1	1.353 (3)	C7—H7B	0.9600
O1—H1	0.8200	C7—H7C	0.9600
O2—C10	1.231 (3)	C8—C9	1.494 (3)
O3—C14	1.371 (3)	C9—H9A	0.9600
O3—C17	1.426 (4)	C9—H9B	0.9600
N1—C8	1.289 (3)	C9—H9C	0.9600
N1—N2	1.385 (3)	C10—C11	1.478 (3)
N2—C10	1.355 (3)	C11—C16	1.384 (3)
N2—H2	0.8600	C11—C12	1.392 (3)
C1—C6	1.386 (4)	C12—C13	1.370 (4)
C1—C2	1.408 (3)	C12—H12	0.9300
C2—C3	1.397 (3)	C13—C14	1.384 (4)
C2—C8	1.472 (3)	C13—H13	0.9300
C3—C4	1.380 (4)	C14—C15	1.373 (4)
C3—H3	0.9300	C15—C16	1.378 (3)
C4—C5	1.377 (4)	C15—H15	0.9300
C4—C7	1.507 (4)	C16—H16	0.9300
C5—C6	1.369 (4)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C7—H7A	0.9600

C1—O1—H1	109.5	C8—C9—H9A	109.5
C14—O3—C17	117.3 (2)	C8—C9—H9B	109.5
C8—N1—N2	119.5 (2)	H9A—C9—H9B	109.5
C10—N2—N1	116.34 (19)	C8—C9—H9C	109.5
C10—N2—H2	121.8	H9A—C9—H9C	109.5
N1—N2—H2	121.8	H9B—C9—H9C	109.5
O1—C1—C6	116.8 (2)	O2—C10—N2	120.4 (2)
O1—C1—C2	123.4 (2)	O2—C10—C11	122.2 (2)
C6—C1—C2	119.7 (2)	N2—C10—C11	117.3 (2)
C3—C2—C1	116.8 (2)	C16—C11—C12	118.1 (2)
C3—C2—C8	121.6 (2)	C16—C11—C10	118.4 (2)
C1—C2—C8	121.6 (2)	C12—C11—C10	123.4 (2)
C4—C3—C2	123.8 (3)	C13—C12—C11	120.7 (2)
C4—C3—H3	118.1	C13—C12—H12	119.7
C2—C3—H3	118.1	C11—C12—H12	119.7
C5—C4—C3	117.1 (3)	C12—C13—C14	120.2 (2)
C5—C4—C7	121.2 (3)	C12—C13—H13	119.9
C3—C4—C7	121.6 (3)	C14—C13—H13	119.9
C6—C5—C4	121.7 (3)	O3—C14—C15	124.5 (3)
C6—C5—H5	119.2	O3—C14—C13	115.5 (2)
C4—C5—H5	119.2	C15—C14—C13	120.0 (3)
C5—C6—C1	120.8 (3)	C14—C15—C16	119.4 (3)
C5—C6—H6	119.6	C14—C15—H15	120.3
C1—C6—H6	119.6	C16—C15—H15	120.3
C4—C7—H7A	109.5	C15—C16—C11	121.5 (2)
C4—C7—H7B	109.5	C15—C16—H16	119.2
H7A—C7—H7B	109.5	C11—C16—H16	119.2
C4—C7—H7C	109.5	O3—C17—H17A	109.5
H7A—C7—H7C	109.5	O3—C17—H17B	109.5
H7B—C7—H7C	109.5	H17A—C17—H17B	109.5
N1—C8—C2	115.3 (2)	O3—C17—H17C	109.5
N1—C8—C9	123.6 (2)	H17A—C17—H17C	109.5
C2—C8—C9	121.1 (2)	H17B—C17—H17C	109.5

C8—N1—N2—C10	−153.5 (2)	C1—C2—C8—C9	177.5 (2)
O1—C1—C2—C3	179.1 (2)	N1—N2—C10—O2	6.6 (3)
C6—C1—C2—C3	−0.5 (3)	N1—N2—C10—C11	−177.19 (18)
O1—C1—C2—C8	0.2 (4)	O2—C10—C11—C16	−26.0 (3)
C6—C1—C2—C8	−179.3 (2)	N2—C10—C11—C16	157.8 (2)
C1—C2—C3—C4	0.7 (4)	O2—C10—C11—C12	149.4 (2)
C8—C2—C3—C4	179.6 (2)	N2—C10—C11—C12	−26.7 (3)
C2—C3—C4—C5	−0.7 (4)	C16—C11—C12—C13	1.5 (4)
C2—C3—C4—C7	−179.7 (2)	C10—C11—C12—C13	−174.0 (2)
C3—C4—C5—C6	0.3 (4)	C11—C12—C13—C14	−1.1 (4)
C7—C4—C5—C6	179.4 (3)	C17—O3—C14—C15	4.8 (4)
C4—C5—C6—C1	−0.1 (4)	C17—O3—C14—C13	−173.8 (2)
O1—C1—C6—C5	−179.4 (2)	C12—C13—C14—O3	177.9 (2)
C2—C1—C6—C5	0.2 (4)	C12—C13—C14—C15	−0.8 (4)
N2—N1—C8—C2	179.61 (17)	O3—C14—C15—C16	−176.3 (2)
N2—N1—C8—C9	1.4 (3)	C13—C14—C15—C16	2.3 (4)
C3—C2—C8—N1	−179.5 (2)	C14—C15—C16—C11	−1.8 (4)
C1—C2—C8—N1	−0.7 (3)	C12—C11—C16—C15	0.0 (4)
C3—C2—C8—C9	−1.2 (3)	C10—C11—C16—C15	175.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.81	2.528 (3)	145
N2—H2···O2ⁱ	0.86	2.17	2.903 (1)	142

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₃
M_r	298.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	15.2171 (13), 4.9253 (4), 20.0906 (16)
β (°)	93.021 (3)
V (Å³)	1503.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.24 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.971, 0.992
No. of measured, independent and observed [I > 2s˘I)] reflections	16192, 2641, 1598
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.178, 1.00
No. of reflections	2641
No. of parameters	204
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.21

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.820	1.814	2.528 (3)	145
N2—H2···O2ⁱ	0.860	2.173	2.903 (1)	142

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

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