(2,4-Dimethoxy­benzyl­idene)-2-hydroxy­benzohydrazide ethanol solvate

Yehye, W.A.; Ariffin, A.; Ng, S.W.

doi:10.1107/S1600536808011768

organic compounds

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Volume 64| Part 6| June 2008| Page o961

doi:10.1107/S1600536808011768

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(2,4-Dimethoxybenzylidene)-2-hydroxybenzohydrazide ethanol solvate

Wagee A. Yehye,^a Azhar Ariffin ^a and Seik Weng Ng ^a ^*

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

(Received 22 April 2008; accepted 24 April 2008; online 3 May 2008)

In the planar title molecule, C₁₆H₁₆N₂O₄·C₂H₆O, the planar Schiff base molecule is linked to the ethanol solvent molecule by a hydroxy–amide hydrogen bond. The hydroxy group of the ethanol molecule is a hydrogen-bond donor to the double-bonded N atom of an adjacent Sciff base, pairs of interactions taking place across a center of symmetry and giving rise to a hydrogen-bonded dimer.

Related literature

For the crystal structures of other substituted benzylidene-2-hydroxybenzohydrazides, see: Li (2007 ); Liang et al. (2005 ); Luo (2007 ); Ma et al. (2005 ); Pan & Yang (2005a ,b ,c ); Qiu et al. (2006 ); Shao et al. (2004 ); Wang et al. (2007 ); Xu & Liu (2006 ); Yang (2006 ); Yang & Pan (2004 , 2005a ,b ); Zhang et al. (2006 ).

Experimental

Crystal data

C₁₆H₁₆N₂O₄·C₂H₆O
M_r = 346.38
Monoclinic, P 2₁ /n
a = 7.7909 (2) Å
b = 18.0539 (6) Å
c = 12.0001 (4) Å
β = 93.803 (2)°
V = 1684.17 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 (2) K
0.20 × 0.15 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
13796 measured reflections
3853 independent reflections
2575 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.118
S = 1.03
3853 reflections
241 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2	0.86 (1)	1.74 (2)	2.528 (2)	151 (2)
O5—H5o⋯N2ⁱ	0.85 (1)	2.07 (1)	2.847 (2)	152 (2)
N1—H1n⋯O5	0.86 (1)	2.09 (1)	2.894 (2)	157 (2)
Symmetry code: (i) -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, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011768/sg2239sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011768/sg2239Isup2.hkl

checkCIF report

Comment top

The crystal structures of a number of substituted benzylidene-2-hydroxybenzohydrazides have been reported (Li, 2007; Liang et al., 2005; Luo, 2007; Ma et al., 2005; Pan & Yang, 2005a,b,c; Qiu et al., 2006; Shao et al., 2004; Wang et al., 2007; Xu & Liu, 2006; Yang, 2006; Yang & Pan, 2004, 2005a,b; Zhang et al., 2006.

The 2,4-dimethoxy derivative crystallizes as an ethanol solvate (Scheme I, Fig. 1). The planar molecule of C₁₆H₁₆N₂O₄ is linked to the ethanol molecule by an amido···hydroxy_ethanol hydrogen bond [N–H···O 2.894 (2) Å]. The hydroxy unit of the ethanol molecule is a hydrogen-bond donor site to the double-bond nitrogen atom of an adjacent Sciff base [O–H···N 2.847 (2) Å], this interaction across a center of symmetry giving rise to a hydrogen-bonded dimer (Fig. 2).

Related literature top

The crystal structures of other substituted benzylidene-2-hydroxybenzohydrazides have been reported; see: Li (2007); Liang et al. (2005); Luo (2007); Ma et al. (2005); Pan & Yang (2005a,b,c); Qiu et al. (2006); Shao et al. (2004); Wang et al. (2007); Xu & Liu (2006); Yang (2006); Yang & Pan (2004, 2005a,b); Zhang et al. (2006).

Experimental top

2-Hydroxybenzohydrazide (0.60 g, 4 mmol) and 2,4-dimethoxybenzaldehyde (0.66 g, 4 mmol) were heated in ethanol (30 ml) for 2 h. The solvent was removed by evaporation and the product 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, 2008).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₆H₁₆N₂O₄^.C₂H₆O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radiius.
	Fig. 2. Hydrogen-bonded dimeric structure.

(2,4-Dimethoxybenzylidene)-2-hydroxybenzohydrazide ethanol solvate top

Crystal data top

C₁₆H₁₆N₂O₄·C₂H₆O	F(000) = 736
M_r = 346.38	D_x = 1.366 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1895 reflections
a = 7.7909 (2) Å	θ = 2.8–25.5°
b = 18.0539 (6) Å	µ = 0.10 mm⁻¹
c = 12.0001 (4) Å	T = 100 K
β = 93.803 (2)°	Prism, colorless
V = 1684.17 (9) Å³	0.20 × 0.15 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	2575 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.059
Graphite monochromator	θ_max = 27.5°, θ_min = 2.0°
ω scans	h = −10→10
13796 measured reflections	k = −20→23
3853 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0476P)² + 0.175P] where P = (F_o² + 2F_c²)/3
3853 reflections	(Δ/σ)_max = 0.001
241 parameters	Δρ_max = 0.21 e Å⁻³
3 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O₄·C₂H₆O	V = 1684.17 (9) Å³
M_r = 346.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.7909 (2) Å	µ = 0.10 mm⁻¹
b = 18.0539 (6) Å	T = 100 K
c = 12.0001 (4) Å	0.20 × 0.15 × 0.15 mm
β = 93.803 (2)°

Data collection top

Bruker SMART APEX diffractometer	2575 reflections with I > 2σ(I)
13796 measured reflections	R_int = 0.059
3853 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	3 restraints
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.21 e Å⁻³
3853 reflections	Δρ_min = −0.25 e Å⁻³
241 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.64682 (15)	0.22307 (7)	0.69448 (11)	0.0248 (3)
O2	0.48542 (15)	0.30514 (7)	0.55256 (10)	0.0253 (3)
O3	0.09164 (14)	0.62457 (7)	0.44328 (10)	0.0224 (3)
O4	−0.15888 (16)	0.55131 (7)	0.07909 (10)	0.0280 (3)
O5	0.45339 (16)	0.56902 (7)	0.68732 (11)	0.0256 (3)
N1	0.40917 (17)	0.42200 (9)	0.59366 (12)	0.0191 (3)
N2	0.32044 (17)	0.42928 (8)	0.48948 (11)	0.0195 (3)
C1	0.6546 (2)	0.28297 (10)	0.76338 (14)	0.0199 (4)
C2	0.7381 (2)	0.27412 (10)	0.86870 (14)	0.0219 (4)
H2	0.7858	0.2275	0.8904	0.026*
C3	0.7514 (2)	0.33316 (11)	0.94120 (14)	0.0231 (4)
H3	0.8073	0.3266	1.0133	0.028*
C4	0.6847 (2)	0.40220 (10)	0.91101 (14)	0.0230 (4)
H4	0.6962	0.4428	0.9614	0.028*
C5	0.6014 (2)	0.41094 (10)	0.80671 (14)	0.0211 (4)
H5	0.5560	0.4581	0.7856	0.025*
C6	0.5825 (2)	0.35172 (10)	0.73132 (14)	0.0180 (4)
C7	0.4908 (2)	0.35796 (10)	0.61929 (14)	0.0192 (4)
C8	0.22902 (19)	0.48872 (10)	0.47864 (14)	0.0188 (4)
H8	0.2277	0.5226	0.5391	0.023*
C9	0.1282 (2)	0.50446 (10)	0.37526 (14)	0.0185 (4)
C10	0.0552 (2)	0.57510 (10)	0.35888 (14)	0.0189 (4)
C11	−0.0433 (2)	0.59274 (10)	0.26156 (14)	0.0197 (4)
H11	−0.0930	0.6405	0.2519	0.024*
C12	−0.0677 (2)	0.53942 (10)	0.17899 (14)	0.0213 (4)
C13	0.0016 (2)	0.46857 (10)	0.19353 (15)	0.0227 (4)
H13	−0.0173	0.4321	0.1369	0.027*
C14	0.0973 (2)	0.45200 (10)	0.29057 (14)	0.0205 (4)
H14	0.1438	0.4036	0.3004	0.025*
C15	0.0125 (2)	0.69592 (10)	0.43449 (15)	0.0240 (4)
H15A	0.0456	0.7250	0.5015	0.036*
H15B	−0.1128	0.6902	0.4275	0.036*
H15C	0.0505	0.7215	0.3685	0.036*
C16	−0.2167 (2)	0.62483 (11)	0.05390 (16)	0.0281 (4)
H16A	−0.2707	0.6264	−0.0222	0.042*
H16B	−0.1184	0.6588	0.0597	0.042*
H16C	−0.3006	0.6398	0.1069	0.042*
C17	0.4115 (2)	0.62589 (11)	0.76362 (15)	0.0278 (4)
H17A	0.5186	0.6506	0.7929	0.033*
H17B	0.3567	0.6033	0.8275	0.033*
C18	0.2921 (2)	0.68255 (11)	0.70951 (16)	0.0310 (5)
H18A	0.2608	0.7187	0.7655	0.046*
H18B	0.1881	0.6579	0.6775	0.046*
H18C	0.3496	0.7079	0.6502	0.046*
H1O	0.594 (3)	0.2375 (13)	0.6331 (12)	0.054 (7)*
H5O	0.518 (2)	0.5858 (13)	0.6389 (15)	0.052 (7)*
H1N	0.410 (3)	0.4596 (8)	0.6371 (14)	0.036 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0311 (7)	0.0185 (7)	0.0241 (7)	0.0015 (5)	−0.0021 (6)	−0.0001 (6)
O2	0.0328 (7)	0.0185 (7)	0.0236 (7)	0.0024 (5)	−0.0045 (5)	−0.0035 (6)
O3	0.0291 (6)	0.0170 (7)	0.0208 (7)	0.0034 (5)	−0.0009 (5)	−0.0022 (5)
O4	0.0342 (7)	0.0261 (8)	0.0225 (7)	0.0032 (6)	−0.0077 (5)	0.0004 (6)
O5	0.0313 (7)	0.0212 (7)	0.0247 (7)	0.0003 (6)	0.0063 (6)	−0.0036 (6)
N1	0.0227 (7)	0.0181 (8)	0.0163 (8)	−0.0002 (6)	−0.0007 (6)	−0.0006 (7)
N2	0.0206 (7)	0.0205 (8)	0.0169 (8)	−0.0006 (6)	−0.0012 (6)	0.0010 (7)
C1	0.0190 (8)	0.0193 (10)	0.0218 (9)	−0.0023 (7)	0.0033 (7)	−0.0003 (8)
C2	0.0212 (8)	0.0210 (10)	0.0233 (10)	0.0009 (7)	0.0000 (7)	0.0044 (8)
C3	0.0224 (8)	0.0285 (11)	0.0183 (9)	−0.0043 (8)	0.0001 (7)	0.0050 (8)
C4	0.0263 (9)	0.0235 (10)	0.0194 (9)	−0.0042 (7)	0.0031 (7)	−0.0034 (8)
C5	0.0221 (8)	0.0181 (10)	0.0232 (10)	−0.0003 (7)	0.0022 (7)	0.0017 (8)
C6	0.0192 (8)	0.0169 (10)	0.0181 (9)	−0.0020 (7)	0.0018 (6)	0.0009 (7)
C7	0.0187 (8)	0.0176 (10)	0.0214 (9)	−0.0012 (7)	0.0024 (7)	−0.0001 (8)
C8	0.0190 (8)	0.0181 (9)	0.0198 (9)	−0.0010 (7)	0.0044 (7)	0.0001 (8)
C9	0.0191 (8)	0.0187 (9)	0.0179 (9)	−0.0014 (7)	0.0032 (6)	0.0005 (8)
C10	0.0181 (8)	0.0193 (10)	0.0196 (9)	−0.0026 (7)	0.0043 (7)	−0.0026 (8)
C11	0.0195 (8)	0.0179 (10)	0.0218 (9)	0.0012 (7)	0.0027 (7)	0.0028 (8)
C12	0.0210 (8)	0.0228 (10)	0.0200 (9)	−0.0026 (7)	0.0009 (7)	0.0018 (8)
C13	0.0253 (9)	0.0206 (10)	0.0218 (10)	−0.0024 (7)	−0.0006 (7)	−0.0034 (8)
C14	0.0217 (8)	0.0158 (9)	0.0240 (10)	−0.0014 (7)	0.0023 (7)	0.0007 (8)
C15	0.0268 (9)	0.0187 (10)	0.0267 (10)	0.0036 (7)	0.0032 (7)	−0.0032 (8)
C16	0.0288 (9)	0.0294 (11)	0.0254 (10)	0.0027 (8)	−0.0031 (8)	0.0047 (9)
C17	0.0319 (10)	0.0270 (11)	0.0245 (10)	0.0004 (8)	0.0026 (8)	−0.0066 (9)
C18	0.0323 (10)	0.0270 (12)	0.0339 (11)	0.0002 (8)	0.0040 (8)	−0.0023 (9)

Geometric parameters (Å, º) top

O1—C1	1.360 (2)	C8—C9	1.452 (2)
O1—H1O	0.859 (9)	C8—H8	0.9500
O2—C7	1.244 (2)	C9—C14	1.398 (2)
O3—C10	1.366 (2)	C9—C10	1.405 (2)
O3—C15	1.429 (2)	C10—C11	1.391 (2)
O4—C12	1.369 (2)	C11—C12	1.385 (2)
O4—C16	1.428 (2)	C11—H11	0.9500
O5—C17	1.428 (2)	C12—C13	1.395 (2)
O5—H5O	0.848 (10)	C13—C14	1.374 (2)
N1—C7	1.345 (2)	C13—H13	0.9500
N1—N2	1.3941 (19)	C14—H14	0.9500
N1—H1N	0.855 (9)	C15—H15A	0.9800
N2—C8	1.290 (2)	C15—H15B	0.9800
C1—C2	1.392 (2)	C15—H15C	0.9800
C1—C6	1.405 (2)	C16—H16A	0.9800
C2—C3	1.375 (2)	C16—H16B	0.9800
C2—H2	0.9500	C16—H16C	0.9800
C3—C4	1.389 (3)	C17—C18	1.501 (3)
C3—H3	0.9500	C17—H17A	0.9900
C4—C5	1.380 (2)	C17—H17B	0.9900
C4—H4	0.9500	C18—H18A	0.9800
C5—C6	1.402 (2)	C18—H18B	0.9800
C5—H5	0.9500	C18—H18C	0.9800
C6—C7	1.485 (2)

C1—O1—H1O	106.2 (16)	C11—C10—C9	121.39 (16)
C10—O3—C15	117.86 (13)	C12—C11—C10	118.89 (16)
C12—O4—C16	117.97 (14)	C12—C11—H11	120.6
C17—O5—H5O	110.7 (17)	C10—C11—H11	120.6
C7—N1—N2	119.00 (15)	O4—C12—C11	123.77 (16)
C7—N1—H1N	123.9 (14)	O4—C12—C13	115.29 (16)
N2—N1—H1N	117.1 (14)	C11—C12—C13	120.94 (16)
C8—N2—N1	113.99 (14)	C14—C13—C12	119.31 (17)
O1—C1—C2	117.39 (16)	C14—C13—H13	120.3
O1—C1—C6	122.35 (15)	C12—C13—H13	120.3
C2—C1—C6	120.27 (16)	C13—C14—C9	121.74 (17)
C3—C2—C1	119.77 (17)	C13—C14—H14	119.1
C3—C2—H2	120.1	C9—C14—H14	119.1
C1—C2—H2	120.1	O3—C15—H15A	109.5
C2—C3—C4	121.28 (16)	O3—C15—H15B	109.5
C2—C3—H3	119.4	H15A—C15—H15B	109.5
C4—C3—H3	119.4	O3—C15—H15C	109.5
C5—C4—C3	118.97 (17)	H15A—C15—H15C	109.5
C5—C4—H4	120.5	H15B—C15—H15C	109.5
C3—C4—H4	120.5	O4—C16—H16A	109.5
C4—C5—C6	121.40 (17)	O4—C16—H16B	109.5
C4—C5—H5	119.3	H16A—C16—H16B	109.5
C6—C5—H5	119.3	O4—C16—H16C	109.5
C5—C6—C1	118.29 (15)	H16A—C16—H16C	109.5
C5—C6—C7	123.38 (16)	H16B—C16—H16C	109.5
C1—C6—C7	118.32 (15)	O5—C17—C18	111.97 (15)
O2—C7—N1	121.10 (16)	O5—C17—H17A	109.2
O2—C7—C6	121.22 (15)	C18—C17—H17A	109.2
N1—C7—C6	117.66 (15)	O5—C17—H17B	109.2
N2—C8—C9	120.86 (16)	C18—C17—H17B	109.2
N2—C8—H8	119.6	H17A—C17—H17B	107.9
C9—C8—H8	119.6	C17—C18—H18A	109.5
C14—C9—C10	117.70 (15)	C17—C18—H18B	109.5
C14—C9—C8	123.06 (16)	H18A—C18—H18B	109.5
C10—C9—C8	119.23 (16)	C17—C18—H18C	109.5
O3—C10—C11	123.27 (16)	H18A—C18—H18C	109.5
O3—C10—C9	115.32 (15)	H18B—C18—H18C	109.5

C7—N1—N2—C8	171.60 (15)	N2—C8—C9—C14	12.2 (2)
O1—C1—C2—C3	179.24 (15)	N2—C8—C9—C10	−168.70 (15)
C6—C1—C2—C3	−0.6 (2)	C15—O3—C10—C11	5.3 (2)
C1—C2—C3—C4	−0.8 (2)	C15—O3—C10—C9	−176.25 (14)
C2—C3—C4—C5	1.0 (2)	C14—C9—C10—O3	−178.97 (14)
C3—C4—C5—C6	0.2 (2)	C8—C9—C10—O3	1.9 (2)
C4—C5—C6—C1	−1.6 (2)	C14—C9—C10—C11	−0.5 (2)
C4—C5—C6—C7	178.61 (15)	C8—C9—C10—C11	−179.61 (15)
O1—C1—C6—C5	−178.08 (14)	O3—C10—C11—C12	177.63 (14)
C2—C1—C6—C5	1.7 (2)	C9—C10—C11—C12	−0.7 (2)
O1—C1—C6—C7	1.8 (2)	C16—O4—C12—C11	6.8 (2)
C2—C1—C6—C7	−178.44 (14)	C16—O4—C12—C13	−173.16 (15)
N2—N1—C7—O2	−1.3 (2)	C10—C11—C12—O4	−178.49 (15)
N2—N1—C7—C6	−179.38 (13)	C10—C11—C12—C13	1.5 (2)
C5—C6—C7—O2	175.88 (16)	O4—C12—C13—C14	179.01 (14)
C1—C6—C7—O2	−4.0 (2)	C11—C12—C13—C14	−0.9 (3)
C5—C6—C7—N1	−6.1 (2)	C12—C13—C14—C9	−0.3 (3)
C1—C6—C7—N1	174.10 (15)	C10—C9—C14—C13	1.0 (2)
N1—N2—C8—C9	−179.75 (14)	C8—C9—C14—C13	−179.89 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2	0.86 (1)	1.74 (2)	2.528 (2)	151 (2)
O5—H5o···N2ⁱ	0.85 (1)	2.07 (1)	2.847 (2)	152 (2)
N1—H1n···O5	0.86 (1)	2.09 (1)	2.894 (2)	157 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₄·C₂H₆O
M_r	346.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.7909 (2), 18.0539 (6), 12.0001 (4)
β (°)	93.803 (2)
V (Å³)	1684.17 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13796, 3853, 2575
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.118, 1.03
No. of reflections	3853
No. of parameters	241
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.25

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2	0.86 (1)	1.74 (2)	2.528 (2)	151 (2)
O5—H5o···N2ⁱ	0.85 (1)	2.07 (1)	2.847 (2)	152 (2)
N1—H1n···O5	0.86 (1)	2.09 (1)	2.894 (2)	157 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We acknowledge the SAGA grant (06–02-03–0147) for support of this study, and the University of Malaya for the purchase of the diffractometer.

References

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