N-Acetyl-2-hydroxy-N′-[methoxy(1-methylindol-2-yl)methyl]benzohydrazide

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

doi:10.1107/S1600536808026846

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1824

doi:10.1107/S1600536808026846

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N-Acetyl-2-hydroxy-N′-[methoxy(1-methylindol-2-yl)methyl]benzohydrazide

Wagee A. Yehye,^a Noorsaadah Abdul Rahman,^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 19 August 2008; accepted 20 August 2008; online 23 August 2008)

In the crystal structure of the title Schiff-base, C₂₀H₂₁N₃O₄, the amino group forms an N—H⋯O hydrogen bond to the acetyl group of an adjacent molecule, forming a zigzag chain. The 2-hydroxy group is internally hydrogen bonded to the amido group though an O—H⋯O hydrogen bond.

Related literature

For medicinal uses of the precursor Schiff base, see: Jin et al. (2006 ); Joshi et al. (2008 ); Szczepankiewicz et al. (2001 ).

Experimental

Crystal data

C₂₀H₂₁N₃O₄
M_r = 367.40
Monoclinic, P 2₁ /n
a = 11.0075 (3) Å
b = 10.5197 (3) Å
c = 15.4479 (4) Å
β = 93.967 (2)°
V = 1784.51 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 (2) K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
16316 measured reflections
4072 independent reflections
2646 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.120
S = 1.02
4072 reflections
255 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2	0.87 (1)	1.81 (2)	2.599 (2)	150 (3)
N1—H1n⋯O3ⁱ	0.85 (1)	2.01 (1)	2.812 (2)	157 (2)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536808026846/tk2298sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026846/tk2298Isup2.hkl

checkCIF report

Comment top

The Schiff base, N'-[(1-methyl-1H-indol-2-yl)methylene]-2-hydroxybenzohydrazide, exhibits useful medicinal properties (Jin et al., 2006; Joshi et al., 2008; Szczepankiewicz et al., 2001). When dissolved in acetic anhydride, the compound undergoes a reaction to yield the title compound, (I), Fig. 1. Essentially, a mole of methyl acetate has been added across the carbon-nitrogen double-bond. In the crystal structure of (I), the amino group forms an N–H···O hydrogen bond to the acetyl group of an adjacent molecule to result in a zigzag chain that runs along the b-axis of the orthorhombic unit cell, Table 1. The 2-hydroxy group is internally hydrogen bonded to the amido group though an O–H···O hydrogen bond, Table 1.

Related literature top

For medicinal uses of the precursor Schiff base, see: Jin et al. (2006); Joshi et al. (2008); Szczepankiewicz et al. (2001).

Experimental top

2-Hydroxybenzohydrazide was condensed with 1-methylindole-3-carboxaldehyde to yield the corresponding Schiff base. To N'-[(1-methyl-1H-indol-2-yl)methylene]-2-hydroxybenzohydrazide (0.88 g, 3 mmol) was added acetic anhydride (10 ml). The mixture was heated to 398–403 K until the reactants dissolved completely. After 2 h of heating, the mixture was cooled and then treated with ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was evaporated and the resulting solid was recrystallized from methanol to give (I) as colorless crystals.

Computing details top

Data collection: APEX2 software (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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of (I) drawn at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

N-Acetyl-2-hydroxy-N'-[methoxy(1-methylindol-2- yl)methyl]benzohydrazide top

Crystal data top

C₂₀H₂₁N₃O₄	F(000) = 776
M_r = 367.40	D_x = 1.367 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1739 reflections
a = 11.0075 (3) Å	θ = 2.2–21.4°
b = 10.5197 (3) Å	µ = 0.10 mm⁻¹
c = 15.4479 (4) Å	T = 100 K
β = 93.967 (2)°	Block, colorless
V = 1784.51 (8) Å³	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	2646 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.065
Graphite monochromator	θ_max = 27.5°, θ_min = 2.2°
ω scans	h = −14→14
16316 measured reflections	k = −13→13
4072 independent reflections	l = −20→20

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0466P)² + 0.3679P] where P = (F_o² + 2F_c²)/3
4072 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.26 e Å⁻³
2 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₀H₂₁N₃O₄	V = 1784.51 (8) Å³
M_r = 367.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.0075 (3) Å	µ = 0.10 mm⁻¹
b = 10.5197 (3) Å	T = 100 K
c = 15.4479 (4) Å	0.20 × 0.15 × 0.10 mm
β = 93.967 (2)°

Data collection top

Bruker SMART APEX diffractometer	2646 reflections with I > 2σ(I)
16316 measured reflections	R_int = 0.065
4072 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	2 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.26 e Å⁻³
4072 reflections	Δρ_min = −0.26 e Å⁻³
255 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.

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

	x	y	z	U_iso*/U_eq
O1	0.75833 (13)	0.62701 (15)	0.28349 (10)	0.0328 (4)
H1O	0.717 (2)	0.5560 (16)	0.2811 (18)	0.069 (10)*
O2	0.57533 (11)	0.47150 (13)	0.28757 (9)	0.0266 (3)
O3	0.27682 (12)	0.25872 (13)	0.22300 (9)	0.0279 (3)
O4	0.41144 (11)	0.35118 (13)	0.43051 (8)	0.0257 (3)
N1	0.38731 (14)	0.55433 (15)	0.29735 (10)	0.0197 (4)
H1N	0.3430 (17)	0.6189 (15)	0.3061 (14)	0.037 (6)*
N2	0.33109 (13)	0.43653 (14)	0.29605 (10)	0.0188 (3)
N3	0.12618 (13)	0.52539 (15)	0.40494 (10)	0.0205 (4)
C1	0.68446 (17)	0.7144 (2)	0.31706 (12)	0.0262 (5)
C2	0.73287 (19)	0.8337 (2)	0.33795 (14)	0.0315 (5)
H2	0.8144	0.8530	0.3262	0.038*
C3	0.6634 (2)	0.9230 (2)	0.37533 (14)	0.0354 (5)
H3	0.6972	1.0042	0.3892	0.042*
C4	0.54370 (19)	0.8971 (2)	0.39356 (13)	0.0308 (5)
H4	0.4966	0.9592	0.4209	0.037*
C5	0.49478 (18)	0.78036 (18)	0.37132 (12)	0.0249 (4)
H5	0.4132	0.7621	0.3837	0.030*
C6	0.56213 (17)	0.68846 (18)	0.33118 (12)	0.0225 (4)
C7	0.51091 (17)	0.56257 (18)	0.30497 (11)	0.0207 (4)
C8	0.31298 (16)	0.36884 (19)	0.22067 (12)	0.0221 (4)
C9	0.33655 (19)	0.4356 (2)	0.13833 (13)	0.0294 (5)
H9A	0.3008	0.3867	0.0889	0.044*
H9B	0.4246	0.4435	0.1337	0.044*
H9C	0.2997	0.5204	0.1383	0.044*
C10	0.30451 (16)	0.38509 (18)	0.38166 (12)	0.0212 (4)
H10	0.2504	0.3091	0.3736	0.025*
C11	0.24263 (16)	0.48432 (18)	0.43178 (12)	0.0208 (4)
C12	0.28551 (17)	0.55066 (18)	0.50327 (12)	0.0227 (4)
H12	0.3624	0.5400	0.5343	0.027*
C13	0.19310 (17)	0.63891 (18)	0.52267 (12)	0.0222 (4)
C14	0.18300 (18)	0.73351 (19)	0.58605 (12)	0.0261 (5)
H14	0.2474	0.7477	0.6291	0.031*
C15	0.07752 (18)	0.8057 (2)	0.58468 (13)	0.0282 (5)
H15	0.0704	0.8708	0.6267	0.034*
C16	−0.01854 (18)	0.7841 (2)	0.52232 (13)	0.0295 (5)
H16	−0.0899	0.8348	0.5230	0.035*
C17	−0.01235 (17)	0.6909 (2)	0.45972 (13)	0.0260 (5)
H17	−0.0785	0.6754	0.4182	0.031*
C18	0.09490 (16)	0.62076 (18)	0.46006 (12)	0.0220 (4)
C19	0.05096 (17)	0.4838 (2)	0.32897 (12)	0.0269 (5)
H19A	−0.0351	0.4872	0.3415	0.040*
H19B	0.0726	0.3963	0.3144	0.040*
H19C	0.0647	0.5397	0.2799	0.040*
C20	0.4677 (2)	0.24041 (19)	0.39780 (14)	0.0313 (5)
H20A	0.5395	0.2183	0.4358	0.047*
H20B	0.4924	0.2574	0.3392	0.047*
H20C	0.4097	0.1696	0.3960	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0245 (7)	0.0335 (9)	0.0408 (9)	−0.0008 (7)	0.0048 (6)	0.0009 (7)
O2	0.0224 (7)	0.0240 (8)	0.0339 (8)	0.0036 (6)	0.0054 (6)	−0.0027 (6)
O3	0.0311 (8)	0.0184 (8)	0.0342 (8)	−0.0058 (6)	0.0016 (6)	−0.0067 (6)
O4	0.0282 (7)	0.0211 (8)	0.0272 (7)	0.0051 (6)	−0.0028 (6)	−0.0001 (6)
N1	0.0201 (8)	0.0107 (8)	0.0284 (9)	−0.0007 (7)	0.0024 (7)	−0.0012 (7)
N2	0.0219 (8)	0.0112 (8)	0.0235 (8)	−0.0031 (6)	0.0023 (6)	−0.0011 (7)
N3	0.0213 (8)	0.0190 (9)	0.0213 (8)	−0.0025 (7)	0.0010 (6)	−0.0028 (7)
C1	0.0270 (10)	0.0277 (12)	0.0236 (10)	−0.0010 (9)	−0.0011 (8)	0.0057 (9)
C2	0.0291 (11)	0.0302 (12)	0.0345 (12)	−0.0109 (10)	−0.0027 (9)	0.0081 (10)
C3	0.0452 (13)	0.0230 (12)	0.0364 (12)	−0.0101 (10)	−0.0088 (10)	0.0048 (10)
C4	0.0420 (13)	0.0197 (11)	0.0297 (11)	−0.0021 (9)	−0.0028 (10)	−0.0017 (9)
C5	0.0296 (10)	0.0209 (11)	0.0239 (10)	−0.0027 (9)	−0.0014 (8)	0.0013 (9)
C6	0.0252 (10)	0.0184 (10)	0.0236 (10)	−0.0025 (8)	0.0000 (8)	0.0049 (8)
C7	0.0243 (10)	0.0205 (10)	0.0172 (9)	−0.0013 (8)	0.0020 (7)	0.0030 (8)
C8	0.0194 (9)	0.0207 (11)	0.0259 (10)	0.0033 (8)	0.0002 (8)	−0.0026 (8)
C9	0.0338 (11)	0.0306 (12)	0.0241 (10)	−0.0007 (10)	0.0028 (9)	−0.0032 (9)
C10	0.0228 (9)	0.0176 (10)	0.0232 (10)	−0.0010 (8)	0.0007 (8)	0.0005 (8)
C11	0.0222 (9)	0.0175 (10)	0.0228 (9)	−0.0016 (8)	0.0022 (8)	0.0017 (8)
C12	0.0238 (10)	0.0231 (11)	0.0213 (9)	0.0003 (8)	0.0008 (8)	0.0007 (8)
C13	0.0251 (10)	0.0199 (10)	0.0218 (10)	−0.0024 (8)	0.0036 (8)	0.0030 (8)
C14	0.0304 (11)	0.0268 (12)	0.0216 (10)	−0.0033 (9)	0.0043 (8)	−0.0024 (9)
C15	0.0356 (11)	0.0238 (11)	0.0263 (10)	0.0006 (9)	0.0090 (9)	−0.0047 (9)
C16	0.0282 (11)	0.0289 (12)	0.0326 (11)	0.0042 (9)	0.0101 (9)	0.0009 (10)
C17	0.0229 (10)	0.0266 (11)	0.0286 (11)	−0.0011 (8)	0.0036 (8)	0.0012 (9)
C18	0.0236 (9)	0.0193 (10)	0.0236 (10)	−0.0040 (8)	0.0059 (8)	0.0000 (8)
C19	0.0247 (10)	0.0279 (12)	0.0274 (11)	−0.0023 (9)	−0.0028 (8)	−0.0050 (9)
C20	0.0367 (12)	0.0185 (11)	0.0378 (12)	0.0085 (9)	−0.0026 (10)	0.0007 (9)

Geometric parameters (Å, º) top

O1—C1	1.354 (2)	C8—C9	1.491 (3)
O1—H1O	0.871 (10)	C9—H9A	0.9800
O2—C7	1.233 (2)	C9—H9B	0.9800
O3—C8	1.226 (2)	C9—H9C	0.9800
O4—C10	1.400 (2)	C10—C11	1.492 (3)
O4—C20	1.428 (2)	C10—H10	1.0000
N1—C7	1.360 (2)	C11—C12	1.363 (3)
N1—N2	1.385 (2)	C12—C13	1.424 (3)
N1—H1N	0.852 (9)	C12—H12	0.9500
N2—C8	1.368 (2)	C13—C14	1.406 (3)
N2—C10	1.477 (2)	C13—C18	1.413 (3)
N3—C18	1.375 (2)	C14—C15	1.387 (3)
N3—C11	1.389 (2)	C14—H14	0.9500
N3—C19	1.456 (2)	C15—C16	1.399 (3)
C1—C2	1.393 (3)	C15—H15	0.9500
C1—C6	1.406 (3)	C16—C17	1.382 (3)
C2—C3	1.365 (3)	C16—H16	0.9500
C2—H2	0.9500	C17—C18	1.392 (3)
C3—C4	1.393 (3)	C17—H17	0.9500
C3—H3	0.9500	C19—H19A	0.9800
C4—C5	1.375 (3)	C19—H19B	0.9800
C4—H4	0.9500	C19—H19C	0.9800
C5—C6	1.390 (3)	C20—H20A	0.9800
C5—H5	0.9500	C20—H20B	0.9800
C6—C7	1.485 (3)	C20—H20C	0.9800

C1—O1—H1O	106.0 (19)	O4—C10—C11	107.19 (14)
C10—O4—C20	112.71 (14)	N2—C10—C11	109.52 (15)
C7—N1—N2	120.11 (16)	O4—C10—H10	109.6
C7—N1—H1N	121.0 (15)	N2—C10—H10	109.6
N2—N1—H1N	117.1 (15)	C11—C10—H10	109.6
C8—N2—N1	121.13 (15)	C12—C11—N3	110.09 (17)
C8—N2—C10	123.05 (15)	C12—C11—C10	129.33 (17)
N1—N2—C10	115.52 (14)	N3—C11—C10	120.52 (16)
C18—N3—C11	107.92 (15)	C11—C12—C13	106.97 (16)
C18—N3—C19	124.45 (16)	C11—C12—H12	126.5
C11—N3—C19	127.50 (16)	C13—C12—H12	126.5
O1—C1—C2	118.06 (18)	C14—C13—C18	118.61 (18)
O1—C1—C6	122.32 (18)	C14—C13—C12	134.43 (18)
C2—C1—C6	119.6 (2)	C18—C13—C12	106.95 (17)
C3—C2—C1	120.1 (2)	C15—C14—C13	118.93 (18)
C3—C2—H2	119.9	C15—C14—H14	120.5
C1—C2—H2	119.9	C13—C14—H14	120.5
C2—C3—C4	121.1 (2)	C14—C15—C16	120.91 (19)
C2—C3—H3	119.4	C14—C15—H15	119.5
C4—C3—H3	119.4	C16—C15—H15	119.5
C5—C4—C3	118.9 (2)	C17—C16—C15	121.71 (19)
C5—C4—H4	120.5	C17—C16—H16	119.1
C3—C4—H4	120.5	C15—C16—H16	119.1
C4—C5—C6	121.40 (19)	C16—C17—C18	117.16 (18)
C4—C5—H5	119.3	C16—C17—H17	121.4
C6—C5—H5	119.3	C18—C17—H17	121.4
C5—C6—C1	118.71 (18)	N3—C18—C17	129.29 (17)
C5—C6—C7	122.54 (17)	N3—C18—C13	108.07 (16)
C1—C6—C7	118.73 (18)	C17—C18—C13	122.64 (18)
O2—C7—N1	121.25 (17)	N3—C19—H19A	109.5
O2—C7—C6	122.64 (17)	N3—C19—H19B	109.5
N1—C7—C6	116.05 (17)	H19A—C19—H19B	109.5
O3—C8—N2	119.69 (18)	N3—C19—H19C	109.5
O3—C8—C9	123.09 (18)	H19A—C19—H19C	109.5
N2—C8—C9	117.21 (17)	H19B—C19—H19C	109.5
C8—C9—H9A	109.5	O4—C20—H20A	109.5
C8—C9—H9B	109.5	O4—C20—H20B	109.5
H9A—C9—H9B	109.5	H20A—C20—H20B	109.5
C8—C9—H9C	109.5	O4—C20—H20C	109.5
H9A—C9—H9C	109.5	H20A—C20—H20C	109.5
H9B—C9—H9C	109.5	H20B—C20—H20C	109.5
O4—C10—N2	111.40 (15)

C7—N1—N2—C8	−84.8 (2)	N1—N2—C10—C11	48.99 (19)
C7—N1—N2—C10	89.2 (2)	C18—N3—C11—C12	0.6 (2)
O1—C1—C2—C3	−177.23 (18)	C19—N3—C11—C12	176.65 (18)
C6—C1—C2—C3	2.8 (3)	C18—N3—C11—C10	−176.91 (16)
C1—C2—C3—C4	0.2 (3)	C19—N3—C11—C10	−0.9 (3)
C2—C3—C4—C5	−1.6 (3)	O4—C10—C11—C12	11.2 (3)
C3—C4—C5—C6	−0.1 (3)	N2—C10—C11—C12	−109.8 (2)
C4—C5—C6—C1	3.0 (3)	O4—C10—C11—N3	−171.84 (16)
C4—C5—C6—C7	−178.81 (18)	N2—C10—C11—N3	67.2 (2)
O1—C1—C6—C5	175.68 (17)	N3—C11—C12—C13	−0.6 (2)
C2—C1—C6—C5	−4.3 (3)	C10—C11—C12—C13	176.68 (18)
O1—C1—C6—C7	−2.6 (3)	C11—C12—C13—C14	−178.7 (2)
C2—C1—C6—C7	177.42 (17)	C11—C12—C13—C18	0.3 (2)
N2—N1—C7—O2	19.8 (3)	C18—C13—C14—C15	−0.2 (3)
N2—N1—C7—C6	−162.92 (15)	C12—C13—C14—C15	178.6 (2)
C5—C6—C7—O2	−163.41 (18)	C13—C14—C15—C16	1.0 (3)
C1—C6—C7—O2	14.8 (3)	C14—C15—C16—C17	−0.2 (3)
C5—C6—C7—N1	19.4 (3)	C15—C16—C17—C18	−1.3 (3)
C1—C6—C7—N1	−162.41 (17)	C11—N3—C18—C17	−179.76 (19)
N1—N2—C8—O3	171.07 (16)	C19—N3—C18—C17	4.0 (3)
C10—N2—C8—O3	−2.5 (3)	C11—N3—C18—C13	−0.4 (2)
N1—N2—C8—C9	−10.1 (2)	C19—N3—C18—C13	−176.59 (17)
C10—N2—C8—C9	176.32 (16)	C16—C17—C18—N3	−178.60 (19)
C20—O4—C10—N2	−71.2 (2)	C16—C17—C18—C13	2.1 (3)
C20—O4—C10—C11	168.97 (15)	C14—C13—C18—N3	179.21 (16)
C8—N2—C10—O4	104.46 (19)	C12—C13—C18—N3	0.1 (2)
N1—N2—C10—O4	−69.42 (19)	C14—C13—C18—C17	−1.4 (3)
C8—N2—C10—C11	−137.13 (17)	C12—C13—C18—C17	179.47 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2	0.87 (1)	1.81 (2)	2.599 (2)	150 (3)
N1—H1n···O3ⁱ	0.85 (1)	2.01 (1)	2.812 (2)	157 (2)

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₁N₃O₄
M_r	367.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	11.0075 (3), 10.5197 (3), 15.4479 (4)
β (°)	93.967 (2)
V (Å³)	1784.51 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16316, 4072, 2646
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.120, 1.02
No. of reflections	4072
No. of parameters	255
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.26

Computer programs: APEX2 software (Bruker, 2007), SAINT (Bruker, 2007), SAINT, 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	0.87 (1)	1.81 (2)	2.599 (2)	150 (3)
N1—H1n···O3ⁱ	0.85 (1)	2.01 (1)	2.812 (2)	157 (2)

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

We thank the University of Malaya for supporting this study (grant No. FS338/2008 A).

References

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