(E)-4-Hy­droxy-N′-(2-meth­oxy­benzyl­idene)benzohydrazide

Rassem, H.H.; Salhin, A.; Bin Salleh, B.; Rosli, M.M.; Fun, H.-K.

doi:10.1107/S1600536812021952

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1832

doi:10.1107/S1600536812021952

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(E)-4-Hydroxy-N′-(2-methoxybenzylidene)benzohydrazide

Hesham Hussein Rassem,^a Abdussalam Salhin,^a ‡ Baharuddin Bin Salleh,^b Mohd Mustaqim Rosli ^c and Hoong-Kun Fun ^c ^*§

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSchool of Biological Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 11 May 2012; accepted 15 May 2012; online 23 May 2012)

In the title compound, C₁₅H₁₄N₂O₃, the dihedral angle between the benzene rings is 66.56 (5)°. In the crystal, N—H⋯O, O—H⋯O and C—H⋯O interactions link the molecules into a three-dimensional network. A π–π interaction, with a centroid–centroid distance of 3.628 (6) Å, helps to establish the packing.

Related literature

For the properties of hydrazone derivatives, see: Lever (1972 ); Pelizzi & Pelizzi (1980 ). For related structures, see: Shan et al. (2003 ); Fun et al. (1996 ); Ferguson et al. (2005 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₃
M_r = 270.28
Orthorhombic, P b c a
a = 14.3951 (3) Å
b = 8.7449 (2) Å
c = 21.1047 (4) Å
V = 2656.74 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.49 × 0.28 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.954, T_max = 0.991
32112 measured reflections
4442 independent reflections
3512 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.114
S = 1.03
4442 reflections
190 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2ⁱ	0.916 (16)	2.009 (16)	2.9202 (12)	172.8 (15)
O1—H1O1⋯O2ⁱⁱ	0.87 (2)	1.80 (2)	2.6528 (11)	164.2 (17)
C13—H13A⋯O1ⁱⁱⁱ	0.95	2.52	3.4669 (15)	171
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812021952/hb6791sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021952/hb6791Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021952/hb6791Isup3.cml

checkCIF report

Comment top

The chemical properties of hydrazone derivatives have been intensively investigated in several research fields mainly due to their facile synthesis, tuneable electronic and steric properties, and good chelating ability (Pelizzi & Pelizzi, 1980). Some derivatives of the title compound, (I), were used for the determination of glucose (Lever, 1972). These compounds crystallize in the E conformation (Shan et al., 2003; Fun et al., 1996) and isomeric compounds have also been prepared (Ferguson et al., 2005).

All parameters in (I), are within normal ranges. The dihedral angle between C1—C6 and C9 C14 benzene ring is 66.56 (5)°. In the crystal structure, the molecules are interconnected by N1—H1N1···O2ⁱ, O1—H1O1···O2ⁱⁱ and C13—H13A···O1ⁱⁱⁱ hydrogen bonds. A π—π interaction with centroid-centroid distance of 3.628 (6) Å also occurs (Cg1 = C9—C14, -x, -y, -z).

Related literature top

For the properties of hydrazone derivatives, see: Lever (1972); Pelizzi & Pelizzi (1980). For related structures, see: Shan et al. (2003); Fun et al. (1996); Ferguson et al. (2005).

Experimental top

A solution of 2-methoxybenzaldehyde (136 mg, 1 mmol) in methanol (10 ml) was added dropwise to a methanolic solution (10 ml) of 4-hydroxybenzhydrazide (152 mg, 1 mmol) and the mixture was refluxed for 2 h. The resulting solution was condensed on a steam bath to 5 ml and cooled to room temperature. Yellow plates were separated out, washed with cooled methanol and dried in air.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure, showing 50% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The crystal packing of (I). Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.

(E)-4-Hydroxy-N'-(2-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 8771 reflections
a = 14.3951 (3) Å	θ = 2.4–31.5°
b = 8.7449 (2) Å	µ = 0.10 mm⁻¹
c = 21.1047 (4) Å	T = 100 K
V = 2656.74 (10) Å³	Plate, yellow
Z = 8	0.49 × 0.28 × 0.09 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	4442 independent reflections
Radiation source: fine-focus sealed tube	3512 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 31.6°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −21→21
T_min = 0.954, T_max = 0.991	k = −12→12
32112 measured reflections	l = −30→31

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0512P)² + 0.959P] where P = (F_o² + 2F_c²)/3
4442 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₃	V = 2656.74 (10) Å³
M_r = 270.28	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.3951 (3) Å	µ = 0.10 mm⁻¹
b = 8.7449 (2) Å	T = 100 K
c = 21.1047 (4) Å	0.49 × 0.28 × 0.09 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	4442 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3512 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.991	R_int = 0.036
32112 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.37 e Å⁻³
4442 reflections	Δρ_min = −0.20 e Å⁻³
190 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.48726 (6)	0.48027 (10)	0.36875 (4)	0.02079 (17)
O2	0.16105 (5)	0.45718 (9)	0.17195 (4)	0.01884 (16)
O3	0.13520 (6)	−0.20688 (9)	0.02729 (4)	0.02154 (18)
N1	0.22355 (7)	0.22544 (11)	0.14758 (4)	0.01752 (18)
N2	0.17102 (6)	0.21485 (11)	0.09246 (4)	0.01848 (19)
C1	0.38142 (7)	0.31733 (13)	0.22565 (5)	0.0181 (2)
H1A	0.3970	0.2544	0.1905	0.022*
C2	0.44845 (7)	0.35161 (13)	0.27091 (5)	0.0184 (2)
H2A	0.5098	0.3130	0.2665	0.022*
C3	0.42528 (7)	0.44303 (13)	0.32286 (5)	0.0170 (2)
C4	0.33481 (8)	0.49850 (14)	0.32950 (5)	0.0204 (2)
H4A	0.3185	0.5583	0.3654	0.024*
C5	0.26913 (7)	0.46623 (13)	0.28374 (5)	0.0187 (2)
H5A	0.2082	0.5066	0.2878	0.022*
C6	0.29126 (7)	0.37485 (12)	0.23154 (5)	0.01578 (19)
C7	0.21981 (7)	0.35457 (12)	0.18194 (5)	0.01583 (19)
C8	0.17442 (7)	0.08270 (13)	0.06597 (5)	0.0185 (2)
H8A	0.2048	0.0008	0.0871	0.022*
C9	0.13238 (7)	0.05622 (13)	0.00393 (5)	0.0176 (2)
C10	0.11156 (8)	0.17623 (13)	−0.03728 (5)	0.0210 (2)
H10A	0.1240	0.2785	−0.0246	0.025*
C11	0.07298 (8)	0.14849 (14)	−0.09648 (5)	0.0229 (2)
H11A	0.0582	0.2310	−0.1240	0.027*
C12	0.05632 (8)	−0.00132 (15)	−0.11500 (5)	0.0227 (2)
H12A	0.0301	−0.0208	−0.1555	0.027*
C13	0.07724 (8)	−0.12288 (14)	−0.07539 (5)	0.0209 (2)
H13A	0.0659	−0.2248	−0.0889	0.025*
C14	0.11498 (7)	−0.09490 (13)	−0.01561 (5)	0.0176 (2)
C15	0.11450 (9)	−0.36068 (13)	0.00934 (6)	0.0237 (2)
H15A	0.1294	−0.4297	0.0445	0.036*
H15B	0.1516	−0.3886	−0.0278	0.036*
H15C	0.0483	−0.3692	−0.0009	0.036*
H1N1	0.2628 (11)	0.1465 (19)	0.1575 (7)	0.027 (4)*
H1O1	0.5437 (14)	0.455 (2)	0.3577 (9)	0.050 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0171 (4)	0.0257 (4)	0.0195 (3)	−0.0008 (3)	−0.0020 (3)	−0.0037 (3)
O2	0.0166 (3)	0.0165 (4)	0.0233 (4)	0.0005 (3)	−0.0012 (3)	−0.0014 (3)
O3	0.0272 (4)	0.0151 (4)	0.0223 (4)	−0.0010 (3)	−0.0063 (3)	0.0006 (3)
N1	0.0184 (4)	0.0148 (4)	0.0194 (4)	−0.0003 (4)	−0.0037 (3)	−0.0015 (3)
N2	0.0178 (4)	0.0190 (4)	0.0187 (4)	−0.0013 (4)	−0.0023 (3)	−0.0012 (3)
C1	0.0176 (5)	0.0176 (5)	0.0192 (4)	−0.0007 (4)	0.0017 (3)	−0.0031 (4)
C2	0.0152 (4)	0.0187 (5)	0.0213 (4)	0.0012 (4)	0.0011 (3)	−0.0024 (4)
C3	0.0169 (4)	0.0167 (5)	0.0174 (4)	−0.0022 (4)	−0.0004 (3)	0.0007 (4)
C4	0.0199 (5)	0.0234 (5)	0.0178 (4)	0.0015 (5)	0.0011 (4)	−0.0039 (4)
C5	0.0169 (4)	0.0201 (5)	0.0191 (4)	0.0021 (4)	0.0010 (4)	−0.0018 (4)
C6	0.0158 (4)	0.0140 (4)	0.0175 (4)	−0.0009 (4)	0.0002 (3)	−0.0005 (4)
C7	0.0153 (4)	0.0146 (5)	0.0175 (4)	−0.0023 (4)	0.0021 (3)	−0.0003 (4)
C8	0.0185 (5)	0.0175 (5)	0.0196 (4)	−0.0014 (4)	−0.0022 (3)	0.0001 (4)
C9	0.0168 (4)	0.0180 (5)	0.0180 (4)	−0.0020 (4)	−0.0007 (3)	−0.0014 (4)
C10	0.0233 (5)	0.0169 (5)	0.0229 (5)	−0.0019 (4)	−0.0017 (4)	0.0007 (4)
C11	0.0258 (5)	0.0215 (5)	0.0213 (5)	−0.0004 (5)	−0.0023 (4)	0.0043 (4)
C12	0.0233 (5)	0.0261 (6)	0.0186 (4)	−0.0013 (5)	−0.0031 (4)	−0.0002 (4)
C13	0.0230 (5)	0.0195 (5)	0.0201 (4)	−0.0016 (5)	−0.0027 (4)	−0.0026 (4)
C14	0.0173 (4)	0.0172 (5)	0.0183 (4)	0.0000 (4)	−0.0008 (3)	−0.0001 (4)
C15	0.0288 (6)	0.0146 (5)	0.0278 (5)	−0.0019 (5)	−0.0038 (4)	−0.0006 (4)

Geometric parameters (Å, º) top

O1—C3	1.3565 (12)	C5—H5A	0.9500
O1—H1O1	0.87 (2)	C6—C7	1.4782 (14)
O2—C7	1.2510 (13)	C8—C9	1.4609 (14)
O3—C14	1.3650 (13)	C8—H8A	0.9500
O3—C15	1.4287 (14)	C9—C10	1.3956 (15)
N1—C7	1.3432 (14)	C9—C14	1.4068 (16)
N1—N2	1.3905 (12)	C10—C11	1.3885 (15)
N1—H1N1	0.917 (16)	C10—H10A	0.9500
N2—C8	1.2848 (14)	C11—C12	1.3880 (17)
C1—C2	1.3904 (14)	C11—H11A	0.9500
C1—C6	1.3974 (15)	C12—C13	1.3856 (16)
C1—H1A	0.9500	C12—H12A	0.9500
C2—C3	1.3973 (15)	C13—C14	1.3953 (14)
C2—H2A	0.9500	C13—H13A	0.9500
C3—C4	1.3969 (15)	C15—H15A	0.9800
C4—C5	1.3806 (15)	C15—H15B	0.9800
C4—H4A	0.9500	C15—H15C	0.9800
C5—C6	1.3978 (14)

C3—O1—H1O1	111.1 (12)	N2—C8—C9	121.12 (10)
C14—O3—C15	117.06 (8)	N2—C8—H8A	119.4
C7—N1—N2	119.07 (9)	C9—C8—H8A	119.4
C7—N1—H1N1	122.3 (9)	C10—C9—C14	119.05 (10)
N2—N1—H1N1	118.5 (9)	C10—C9—C8	121.89 (10)
C8—N2—N1	113.78 (9)	C14—C9—C8	119.03 (10)
C2—C1—C6	120.38 (10)	C11—C10—C9	121.01 (11)
C2—C1—H1A	119.8	C11—C10—H10A	119.5
C6—C1—H1A	119.8	C9—C10—H10A	119.5
C1—C2—C3	119.79 (10)	C12—C11—C10	119.17 (10)
C1—C2—H2A	120.1	C12—C11—H11A	120.4
C3—C2—H2A	120.1	C10—C11—H11A	120.4
O1—C3—C4	117.28 (9)	C13—C12—C11	121.11 (10)
O1—C3—C2	122.73 (10)	C13—C12—H12A	119.4
C4—C3—C2	119.99 (10)	C11—C12—H12A	119.4
C5—C4—C3	119.82 (10)	C12—C13—C14	119.72 (11)
C5—C4—H4A	120.1	C12—C13—H13A	120.1
C3—C4—H4A	120.1	C14—C13—H13A	120.1
C4—C5—C6	120.81 (10)	O3—C14—C13	123.85 (10)
C4—C5—H5A	119.6	O3—C14—C9	116.20 (9)
C6—C5—H5A	119.6	C13—C14—C9	119.93 (10)
C1—C6—C5	119.18 (9)	O3—C15—H15A	109.5
C1—C6—C7	122.68 (9)	O3—C15—H15B	109.5
C5—C6—C7	117.92 (9)	H15A—C15—H15B	109.5
O2—C7—N1	122.63 (9)	O3—C15—H15C	109.5
O2—C7—C6	120.24 (9)	H15A—C15—H15C	109.5
N1—C7—C6	117.09 (9)	H15B—C15—H15C	109.5

C7—N1—N2—C8	−175.07 (10)	N1—N2—C8—C9	−172.79 (9)
C6—C1—C2—C3	0.55 (17)	N2—C8—C9—C10	19.20 (16)
C1—C2—C3—O1	179.77 (10)	N2—C8—C9—C14	−162.77 (10)
C1—C2—C3—C4	0.59 (17)	C14—C9—C10—C11	0.93 (17)
O1—C3—C4—C5	179.00 (10)	C8—C9—C10—C11	178.95 (10)
C2—C3—C4—C5	−1.77 (17)	C9—C10—C11—C12	−0.96 (18)
C3—C4—C5—C6	1.84 (17)	C10—C11—C12—C13	0.22 (18)
C2—C1—C6—C5	−0.50 (16)	C11—C12—C13—C14	0.54 (18)
C2—C1—C6—C7	173.99 (10)	C15—O3—C14—C13	−1.07 (16)
C4—C5—C6—C1	−0.70 (16)	C15—O3—C14—C9	177.53 (10)
C4—C5—C6—C7	−175.45 (10)	C12—C13—C14—O3	177.98 (10)
N2—N1—C7—O2	10.90 (15)	C12—C13—C14—C9	−0.57 (16)
N2—N1—C7—C6	−166.78 (9)	C10—C9—C14—O3	−178.81 (10)
C1—C6—C7—O2	−145.49 (11)	C8—C9—C14—O3	3.10 (14)
C5—C6—C7—O2	29.07 (15)	C10—C9—C14—C13	−0.15 (16)
C1—C6—C7—N1	32.25 (15)	C8—C9—C14—C13	−178.24 (10)
C5—C6—C7—N1	−153.19 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2ⁱ	0.916 (16)	2.009 (16)	2.9202 (12)	172.8 (15)
O1—H1O1···O2ⁱⁱ	0.87 (2)	1.80 (2)	2.6528 (11)	164.2 (17)
C13—H13A···O1ⁱⁱⁱ	0.95	2.52	3.4669 (15)	171

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₃
M_r	270.28
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	14.3951 (3), 8.7449 (2), 21.1047 (4)
V (Å³)	2656.74 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.49 × 0.28 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.954, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	32112, 4442, 3512
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.737

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.114, 1.03
No. of reflections	4442
No. of parameters	190
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.20

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2ⁱ	0.916 (16)	2.009 (16)	2.9202 (12)	172.8 (15)
O1—H1O1···O2ⁱⁱ	0.87 (2)	1.80 (2)	2.6528 (11)	164.2 (17)
C13—H13A···O1ⁱⁱⁱ	0.95	2.52	3.4669 (15)	171

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

Footnotes

‡Additional correspondence author, e-mail: abdussalam@usm.my.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

We thank Universiti Sains Malaysia for awarding an RU (1001/PKIMIA/811196) grant. HKF thank USM for the Research University Grant No. 1001/PFIZIK/811160.

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