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

Mohd Lair, N.; Mohd Ali, H.; Ng, S.W.

doi:10.1107/S1600536808042888

organic compounds

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Volume 65| Part 1| January 2009| Page o189

doi:10.1107/S1600536808042888

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

Nooraziah Mohd Lair,^a Hapipah Mohd Ali ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 December 2008; accepted 16 December 2008; online 20 December 2008)

The Schiff base molecule of the title compound, C₁₅H₁₄N₂O₄·H₂O, adopts a trans configuration with respect to the C=N double bond; the Schiff base itself is almost planar (r.m.s. deviation for all non-H atoms = 0.040 Å). The amido N atom is the hydrogen-bond donor to the water molecule, which is the hydrogen-bond donor to the hydroxy groups of two neighboring molecules. One of the hydroxyl groups acts as an intramolecular and the other as an intermolecular hydrogen-bond donor.

Related literature

For the structure of (E)-4-chloro-N′-(2-hydroxy-3-methoxybenzylidene)benzohydrazide, which crystallizes as a monohydrate, see: Cui et al. (2007 ). For a series of similar compounds, see: Lu et al. (2008a ,b ,c ). For this and other compounds with antimalarial properties, see: Melnyk et al. (2006 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₄·H₂O
M_r = 304.30
Monoclinic, P 2₁ /n
a = 7.1763 (2) Å
b = 16.6507 (5) Å
c = 12.1828 (4) Å
β = 98.022 (2)°
V = 1441.48 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 (2) K
0.16 × 0.04 × 0.04 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
13327 measured reflections
3315 independent reflections
1903 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.180
S = 1.05
3315 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.84	1.86	2.621 (3)	150
O3—H3⋯N2	0.84	1.94	2.575 (3)	132
O5—H51⋯O1ⁱⁱ	0.84	2.03	2.833 (3)	160
O5—H52⋯O3ⁱⁱⁱ	0.84	2.27	3.070 (4)	160
N1—H11⋯O5	0.88	2.05	2.883 (3)	158
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+2; (iii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042888/bt2836sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808042888/bt2836Isup2.hkl

checkCIF report

Related literature top

For (E)-4-chloro-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide, which crystallizes as a monohydrate, see: Cui et al. (2007). For a set of similar compounds, see: Lu et al. (2008a,b,c). For compounds with antimalarial properties, see: Melnyk et al. (2006).

Experimental top

2-Hydroxy-3-methoxybenzaldehyde (0.30 g, 2 mmol) and 4-hydroxybenzohydrazide (0.30 g, 2 mmol) were heated in an ethanol-methanol mixture (50 ml) for 2 h. The solvent was removed and the resulting compound recrystallized from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₁₅H₁₄N₂O₄^.H₂O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

(E)-4-Hydroxy-N'-(2-hydroxy-4-methoxybenzylidene)benzohydrazide monohydrate top

Crystal data top

C₁₅H₁₄N₂O₄·H₂O	F(000) = 640
M_r = 304.30	D_x = 1.402 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1918 reflections
a = 7.1763 (2) Å	θ = 2.4–27.3°
b = 16.6507 (5) Å	µ = 0.11 mm⁻¹
c = 12.1828 (4) Å	T = 100 K
β = 98.022 (2)°	Prism, yellow
V = 1441.48 (8) Å³	0.16 × 0.04 × 0.04 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	1903 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.053
Graphite monochromator	θ_max = 27.5°, θ_min = 2.1°
ω scans	h = −9→9
13327 measured reflections	k = −21→21
3315 independent reflections	l = −15→15

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.180	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0687P)² + 1.4764P] where P = (F_o² + 2F_c²)/3
3315 reflections	(Δ/σ)_max = 0.001
200 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₄·H₂O	V = 1441.48 (8) Å³
M_r = 304.30	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.1763 (2) Å	µ = 0.11 mm⁻¹
b = 16.6507 (5) Å	T = 100 K
c = 12.1828 (4) Å	0.16 × 0.04 × 0.04 mm
β = 98.022 (2)°

Data collection top

Bruker SMART APEX diffractometer	1903 reflections with I > 2σ(I)
13327 measured reflections	R_int = 0.053
3315 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.180	H-atom parameters constrained
S = 1.05	Δρ_max = 0.66 e Å⁻³
3315 reflections	Δρ_min = −0.43 e Å⁻³
200 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.7450 (3)	0.31702 (12)	1.09538 (15)	0.0271 (5)
H1	0.7745	0.2698	1.1150	0.041*
O2	0.3884 (3)	0.32742 (11)	0.58919 (15)	0.0246 (5)
O3	0.1758 (3)	0.41831 (13)	0.32215 (18)	0.0444 (6)
H3	0.2262	0.4067	0.3866	0.067*
O4	−0.1014 (3)	0.59721 (14)	0.05179 (16)	0.0359 (6)
O5	0.4249 (4)	0.61425 (14)	0.73043 (18)	0.0495 (7)
H51	0.4027	0.6363	0.7892	0.074*
H52	0.5420	0.6108	0.7317	0.074*
N1	0.3620 (3)	0.45875 (14)	0.62786 (18)	0.0208 (5)
H11	0.3800	0.4987	0.6754	0.025*
N2	0.2800 (3)	0.47111 (14)	0.51985 (17)	0.0218 (5)
C1	0.4997 (3)	0.36829 (15)	0.7739 (2)	0.0174 (5)
C2	0.5351 (4)	0.42869 (16)	0.8536 (2)	0.0204 (6)
H2	0.5012	0.4826	0.8345	0.024*
C3	0.6192 (4)	0.41082 (16)	0.9602 (2)	0.0216 (6)
H3A	0.6449	0.4524	1.0135	0.026*
C4	0.6653 (3)	0.33229 (16)	0.9886 (2)	0.0197 (6)
C5	0.6322 (4)	0.27144 (16)	0.9108 (2)	0.0214 (6)
H5A	0.6655	0.2176	0.9305	0.026*
C6	0.5504 (4)	0.28976 (16)	0.8043 (2)	0.0208 (6)
H6	0.5284	0.2481	0.7508	0.025*
C7	0.4134 (3)	0.38292 (16)	0.6579 (2)	0.0191 (6)
C8	0.2221 (4)	0.54217 (18)	0.4913 (2)	0.0231 (6)
H8	0.2362	0.5848	0.5436	0.028*
C9	0.1350 (4)	0.55631 (18)	0.3780 (2)	0.0235 (6)
C10	0.1117 (4)	0.49462 (18)	0.2982 (2)	0.0289 (7)
C11	0.0295 (4)	0.5107 (2)	0.1905 (2)	0.0329 (7)
H11A	0.0125	0.4689	0.1371	0.040*
C12	−0.0278 (4)	0.5882 (2)	0.1614 (2)	0.0281 (7)
C13	−0.0097 (4)	0.64983 (19)	0.2380 (2)	0.0290 (7)
H13	−0.0519	0.7025	0.2177	0.035*
C14	0.0714 (4)	0.63284 (18)	0.3450 (2)	0.0270 (6)
H14	0.0843	0.6749	0.3982	0.032*
C15	−0.1581 (4)	0.6759 (2)	0.0151 (3)	0.0385 (8)
H15A	−0.2026	0.6749	−0.0647	0.058*
H15B	−0.0508	0.7127	0.0299	0.058*
H15C	−0.2598	0.6944	0.0549	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0379 (11)	0.0266 (11)	0.0146 (9)	0.0096 (9)	−0.0039 (8)	0.0015 (8)
O2	0.0309 (10)	0.0230 (10)	0.0188 (10)	−0.0048 (8)	−0.0008 (8)	−0.0005 (8)
O3	0.0701 (17)	0.0318 (13)	0.0264 (12)	−0.0012 (12)	−0.0107 (11)	0.0029 (10)
O4	0.0320 (12)	0.0538 (15)	0.0203 (10)	0.0041 (10)	−0.0018 (9)	0.0118 (10)
O5	0.0772 (18)	0.0431 (14)	0.0259 (12)	0.0265 (13)	−0.0009 (12)	−0.0119 (11)
N1	0.0228 (12)	0.0233 (12)	0.0152 (11)	0.0005 (9)	−0.0016 (9)	0.0003 (9)
N2	0.0209 (11)	0.0306 (13)	0.0132 (11)	−0.0014 (10)	0.0004 (9)	0.0039 (9)
C1	0.0136 (12)	0.0223 (13)	0.0164 (13)	−0.0033 (10)	0.0020 (10)	−0.0001 (11)
C2	0.0201 (13)	0.0213 (14)	0.0197 (13)	0.0023 (10)	0.0027 (10)	0.0031 (11)
C3	0.0260 (14)	0.0207 (14)	0.0172 (13)	0.0012 (11)	0.0001 (10)	−0.0035 (11)
C4	0.0192 (13)	0.0249 (14)	0.0144 (12)	0.0032 (11)	0.0007 (10)	0.0034 (11)
C5	0.0221 (13)	0.0201 (14)	0.0214 (13)	0.0022 (11)	0.0006 (11)	0.0011 (11)
C6	0.0217 (13)	0.0228 (14)	0.0170 (13)	−0.0005 (11)	−0.0004 (11)	−0.0033 (11)
C7	0.0173 (13)	0.0225 (14)	0.0176 (13)	−0.0027 (10)	0.0029 (10)	0.0000 (11)
C8	0.0197 (13)	0.0303 (15)	0.0195 (14)	0.0004 (11)	0.0035 (11)	0.0013 (12)
C9	0.0184 (13)	0.0327 (16)	0.0198 (14)	−0.0033 (11)	0.0043 (11)	0.0066 (12)
C10	0.0333 (16)	0.0286 (16)	0.0242 (14)	−0.0018 (13)	0.0013 (12)	0.0074 (13)
C11	0.0371 (17)	0.0391 (18)	0.0211 (15)	−0.0053 (14)	−0.0013 (12)	0.0008 (13)
C12	0.0192 (14)	0.0471 (19)	0.0177 (14)	−0.0008 (13)	0.0011 (11)	0.0108 (13)
C13	0.0237 (14)	0.0358 (17)	0.0269 (16)	0.0055 (12)	0.0018 (12)	0.0123 (13)
C14	0.0235 (14)	0.0327 (16)	0.0249 (15)	0.0039 (12)	0.0043 (12)	0.0033 (12)
C15	0.0314 (17)	0.057 (2)	0.0263 (16)	0.0062 (16)	0.0018 (13)	0.0173 (16)

Geometric parameters (Å, º) top

O1—C4	1.370 (3)	C3—H3A	0.9500
O1—H1	0.8400	C4—C5	1.385 (4)
O2—C7	1.243 (3)	C5—C6	1.382 (4)
O3—C10	1.369 (4)	C5—H5A	0.9500
O3—H3	0.8400	C6—H6	0.9500
O4—C12	1.374 (3)	C8—C9	1.452 (4)
O4—C15	1.426 (4)	C8—H8	0.9500
O5—H51	0.8400	C9—C14	1.394 (4)
O5—H52	0.8400	C9—C10	1.408 (4)
N1—C7	1.351 (3)	C10—C11	1.387 (4)
N1—N2	1.380 (3)	C11—C12	1.385 (4)
N1—H11	0.8800	C11—H11A	0.9500
N2—C8	1.286 (4)	C12—C13	1.381 (4)
C1—C6	1.393 (4)	C13—C14	1.381 (4)
C1—C2	1.396 (4)	C13—H13	0.9500
C1—C7	1.482 (3)	C14—H14	0.9500
C2—C3	1.386 (4)	C15—H15A	0.9800
C2—H2	0.9500	C15—H15B	0.9800
C3—C4	1.381 (4)	C15—H15C	0.9800

C4—O1—H1	119.9	N1—C7—C1	118.3 (2)
C10—O3—H3	120.0	N2—C8—C9	119.1 (3)
C12—O4—C15	117.3 (3)	N2—C8—H8	120.5
H51—O5—H52	108.8	C9—C8—H8	120.5
C7—N1—N2	117.5 (2)	C14—C9—C10	117.7 (3)
C7—N1—H11	121.3	C14—C9—C8	120.2 (3)
N2—N1—H11	121.3	C10—C9—C8	122.1 (3)
C8—N2—N1	118.3 (2)	O3—C10—C11	117.8 (3)
C6—C1—C2	118.4 (2)	O3—C10—C9	121.7 (3)
C6—C1—C7	117.8 (2)	C11—C10—C9	120.4 (3)
C2—C1—C7	123.8 (2)	C12—C11—C10	119.6 (3)
C3—C2—C1	120.7 (2)	C12—C11—H11A	120.2
C3—C2—H2	119.7	C10—C11—H11A	120.2
C1—C2—H2	119.7	O4—C12—C13	124.3 (3)
C4—C3—C2	119.8 (2)	O4—C12—C11	114.2 (3)
C4—C3—H3A	120.1	C13—C12—C11	121.5 (3)
C2—C3—H3A	120.1	C12—C13—C14	118.3 (3)
O1—C4—C3	117.9 (2)	C12—C13—H13	120.9
O1—C4—C5	121.5 (2)	C14—C13—H13	120.9
C3—C4—C5	120.5 (2)	C13—C14—C9	122.5 (3)
C6—C5—C4	119.4 (2)	C13—C14—H14	118.7
C6—C5—H5A	120.3	C9—C14—H14	118.7
C4—C5—H5A	120.3	O4—C15—H15A	109.5
C5—C6—C1	121.2 (2)	O4—C15—H15B	109.5
C5—C6—H6	119.4	H15A—C15—H15B	109.5
C1—C6—H6	119.4	O4—C15—H15C	109.5
O2—C7—N1	120.3 (2)	H15A—C15—H15C	109.5
O2—C7—C1	121.4 (2)	H15B—C15—H15C	109.5

C7—N1—N2—C8	176.8 (2)	N2—C8—C9—C14	−179.9 (3)
C6—C1—C2—C3	0.2 (4)	N2—C8—C9—C10	0.0 (4)
C7—C1—C2—C3	−178.9 (2)	C14—C9—C10—O3	177.7 (3)
C1—C2—C3—C4	−1.2 (4)	C8—C9—C10—O3	−2.2 (4)
C2—C3—C4—O1	−178.8 (2)	C14—C9—C10—C11	0.6 (4)
C2—C3—C4—C5	1.5 (4)	C8—C9—C10—C11	−179.3 (3)
O1—C4—C5—C6	179.6 (2)	O3—C10—C11—C12	−176.4 (3)
C3—C4—C5—C6	−0.7 (4)	C9—C10—C11—C12	0.8 (4)
C4—C5—C6—C1	−0.3 (4)	C15—O4—C12—C13	1.6 (4)
C2—C1—C6—C5	0.6 (4)	C15—O4—C12—C11	−178.2 (3)
C7—C1—C6—C5	179.7 (2)	C10—C11—C12—O4	178.0 (3)
N2—N1—C7—O2	0.7 (4)	C10—C11—C12—C13	−1.8 (4)
N2—N1—C7—C1	−179.3 (2)	O4—C12—C13—C14	−178.4 (3)
C6—C1—C7—O2	−0.7 (4)	C11—C12—C13—C14	1.4 (4)
C2—C1—C7—O2	178.4 (2)	C12—C13—C14—C9	0.0 (4)
C6—C1—C7—N1	179.3 (2)	C10—C9—C14—C13	−1.0 (4)
C2—C1—C7—N1	−1.6 (4)	C8—C9—C14—C13	178.9 (3)
N1—N2—C8—C9	−179.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.84	1.86	2.621 (3)	150
O3—H3···N2	0.84	1.94	2.575 (3)	132
O5—H51···O1ⁱⁱ	0.84	2.03	2.833 (3)	160
O5—H52···O3ⁱⁱⁱ	0.84	2.27	3.070 (4)	160
N1—H11···O5	0.88	2.05	2.883 (3)	158

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₄·H₂O
M_r	304.30
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.1763 (2), 16.6507 (5), 12.1828 (4)
β (°)	98.022 (2)
V (Å³)	1441.48 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.16 × 0.04 × 0.04

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13327, 3315, 1903
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.180, 1.05
No. of reflections	3315
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.43

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.84	1.86	2.621 (3)	150
O3—H3···N2	0.84	1.94	2.575 (3)	132
O5—H51···O1ⁱⁱ	0.84	2.03	2.833 (3)	160
O5—H52···O3ⁱⁱⁱ	0.84	2.27	3.070 (4)	160
N1—H11···O5	0.88	2.05	2.883 (3)	158

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

Acknowledgements

We thank the University of Malaya for funding this study (Science Fund grants 12–02-03–2031, 12–02-03–2051).

References

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Volume 65| Part 1| January 2009| Page o189

doi:10.1107/S1600536808042888

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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