2-[(E)-(2,4-Dihy­droxy­benzyl­idene)aza­nium­yl]-3-phenyl­propano­ate

Bahron, H.; Fadzel, F.M.; Kassim, K.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536811016655

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1331-o1332

doi:10.1107/S1600536811016655

Open

access

2-[(E)-(2,4-Dihydroxybenzylidene)azaniumyl]-3-phenylpropanoate

Hadariah Bahron,^a ‡ Fatimatuzzahraa Mohd Fadzel,^a Karimah Kassim,^a Madhukar Hemamalini ^b and Hoong-Kun Fun ^b ^*§

^aFaculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 26 April 2011; accepted 3 May 2011; online 7 May 2011)

The title compound, C₁₆H₁₅NO₄, exists as a zwitterion in the solid state, with the carboxylic acid group being deprotonated and the imine N atom being protonated. The molecule adopts an E configuration about the C=N double bond. The dihedral angle between the benzene rings is 46.34 (4)°. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, adjacent molecules are connected by intermolecular O—H⋯O and C—H⋯O hydrogen bonds, forming supramolecular ribbons along the a axis.

Related literature

For details of Schiff bases and their applications, see: Dolaz et al. (2009 ); Kumar et al. (2010 ); Qiao et al. (2011 ); Sauri et al. (2009 ); Tamami & Ghasemi (2011 ). For related structures, see: Bahron et al. (2010 ); Hemamalini & Fun (2011 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₅NO₄
M_r = 285.29
Monoclinic, P 2₁ /c
a = 9.3943 (1) Å
b = 6.8946 (1) Å
c = 20.7251 (3) Å
β = 92.065 (1)°
V = 1341.49 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.34 × 0.27 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.966, T_max = 0.982
22479 measured reflections
6007 independent reflections
4783 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.125
S = 1.03
6007 reflections
202 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.56 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—H1O1⋯O4ⁱ	0.863 (15)	1.790 (14)	2.6302 (9)	163.9 (15)
N1—H1N1⋯O1	0.864 (14)	2.051 (15)	2.6810 (9)	129.1 (12)
O2—H1O2⋯O3ⁱⁱ	1.03 (2)	1.51 (2)	2.5310 (10)	179 (2)
C5—H5A⋯O2ⁱⁱⁱ	0.95	2.56	3.3155 (10)	137
C12—H12A⋯O2^iv	0.95	2.46	3.1781 (10)	132
Symmetry codes: (i) -x+1, -y+2, -z; (ii) x+1, y-1, z; (iii) x-1, y, z; (iv) -x+2, -y+1, -z.

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 global, I. DOI: 10.1107/S1600536811016655/rz2592sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016655/rz2592Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811016655/rz2592Isup3.cml

checkCIF report

Comment top

Schiff bases have received considerable attention and remain important in the field of coordination chemistry vastly due to their simple synthesis and versatility. They are widely reported to have extensive potential applications in various biological and pharmaceutical fields (Dolaz et al., 2009) as antimicrobial (Kumar et al., 2010) and antitumor (Qiao et al., 2011) agents. They also display potential applications as corrosion inhibitors (Sauri et al., 2009) and catalysts (Tamami & Ghasemi, 2011). The title molecule, (I), is a Schiff base derived from DL-phenylalanine and 2,4-dihydroxybenzaldehyde using the procedure reported by Bahron et al. (2010). It crystallizes as a zwitterion in which the imine N is protonated. A similar zwitterionic structure was reported by Hemamalini & Fun (2011).

The asymmetric unit of the title compound is shown in Fig. 1. The molecule is a zwitterion in the crystal, with the carboxylic acid group deprotonated and the imine N atom protonated. It adopts an E configuration about the central C9═N1 double bond [1.3045 (3) Å] with the torsion angle C10-C9-N1-C8 = -175.36 (7)°. The dihedral angle between the benzene (C10–C15) and phenyl (C1–C6) rings is 46.34 (4)°.

In the crystal structure (Fig. 2), an intramolecular N1—H1N1···O1 hydrogen bond (Table 1) generates an S(6) ring motif (Bernstein et al., 1995). Furthermore, adjacent molecules are connected by intermolecular O1—H1O1···O4, O2—H1O2···O3, C5—H5A···O2 and C12—H12A···O2 (Table 1) hydrogen bonds forming supramolecular ribbons along the a axis.

Related literature top

For details of Schiff bases and their applications, see: Dolaz et al. (2009); Kumar et al. (2010); Qiao et al. (2011); Sauri et al. (2009); Tamami & Ghasemi (2011). For related structures, see: Bahron et al. (2010); Hemamalini & Fun (2011). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

DL-phenylalanine (2 mmol, 0.330 g ) was dissolved in absolute ethanol (20 mL), into which 2,4-dihydroxybenzaldehyde (2 mmol, 0.276 g) was added, followed by refluxing for two hours. The solution was left to slowly cool to room temperature upon which pale orange crystals were produced. These were filtered off, washed with ice-cold ethanol and air dried (yield 68%). Melting point: 540–543 K. Analytical calculated for C₁₆H₁₅NO₄ (%): C, 67.36; H, 5.30; N, 4.91. Found (%): C, 67.13; H, 5.49; N, 4.89. IR (cm^-1): ν(C═N) 1642.9 (m), ν(C–OH) 1243.7 (w), ν(C═O) 1880.6 (w).

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 asymmetric unit of the title compound, showing 50% probability displacement ellipsoids. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound with hydrogen bonds shown as dashed lines. H atoms not involved in the intermolecular interactions have been omitted for clarity.

2-[(E)-(2,4-Dihydroxybenzylidene)azaniumyl]-3-phenylpropanoate top

Crystal data top

C₁₆H₁₅NO₄	F(000) = 600
M_r = 285.29	D_x = 1.413 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9091 reflections
a = 9.3943 (1) Å	θ = 3.0–35.3°
b = 6.8946 (1) Å	µ = 0.10 mm⁻¹
c = 20.7251 (3) Å	T = 100 K
β = 92.065 (1)°	Block, orange
V = 1341.49 (3) Å³	0.34 × 0.27 × 0.17 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6007 independent reflections
Radiation source: fine-focus sealed tube	4783 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 35.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→13
T_min = 0.966, T_max = 0.982	k = −8→11
22479 measured reflections	l = −33→32

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0674P)² + 0.2835P] where P = (F_o² + 2F_c²)/3
6007 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₆H₁₅NO₄	V = 1341.49 (3) Å³
M_r = 285.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.3943 (1) Å	µ = 0.10 mm⁻¹
b = 6.8946 (1) Å	T = 100 K
c = 20.7251 (3) Å	0.34 × 0.27 × 0.17 mm
β = 92.065 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6007 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4783 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.982	R_int = 0.025
22479 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.56 e Å⁻³
6007 reflections	Δρ_min = −0.24 e Å⁻³
202 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.60361 (6)	0.80079 (9)	0.04375 (3)	0.01400 (12)
O2	0.97519 (6)	0.33854 (10)	0.05402 (3)	0.01685 (13)
O3	0.03702 (7)	0.98745 (10)	0.07713 (4)	0.01988 (14)
O4	0.26610 (7)	1.04016 (9)	0.05323 (3)	0.01783 (13)
N1	0.34885 (7)	0.69321 (10)	0.08580 (3)	0.01219 (12)
C1	0.33058 (10)	0.53563 (14)	0.25232 (4)	0.01942 (16)
H1A	0.3954	0.6401	0.2590	0.023*
C2	0.35367 (11)	0.36077 (15)	0.28493 (5)	0.02434 (19)
H2A	0.4337	0.3473	0.3139	0.029*
C3	0.26067 (12)	0.20648 (14)	0.27537 (5)	0.02416 (19)
H3A	0.2770	0.0875	0.2975	0.029*
C4	0.14316 (11)	0.22715 (13)	0.23307 (5)	0.02018 (17)
H4A	0.0792	0.1219	0.2262	0.024*
C5	0.11937 (9)	0.40174 (13)	0.20089 (4)	0.01695 (15)
H5A	0.0386	0.4150	0.1723	0.020*
C6	0.21269 (9)	0.55797 (12)	0.20999 (4)	0.01422 (14)
C7	0.18457 (9)	0.74664 (12)	0.17511 (4)	0.01563 (15)
H7A	0.2505	0.8462	0.1933	0.019*
H7B	0.0863	0.7891	0.1836	0.019*
C8	0.20180 (8)	0.73766 (12)	0.10126 (4)	0.01250 (13)
H8A	0.1359	0.6381	0.0817	0.015*
C9	0.40809 (8)	0.52254 (11)	0.09102 (4)	0.01214 (13)
H9A	0.3492	0.4173	0.1029	0.015*
C10	0.55370 (8)	0.48144 (11)	0.08037 (4)	0.01121 (13)
C11	0.65246 (8)	0.61982 (11)	0.05775 (4)	0.01132 (13)
C12	0.79342 (8)	0.56952 (12)	0.04987 (4)	0.01286 (14)
H12A	0.8591	0.6634	0.0354	0.015*
C13	0.83916 (8)	0.37933 (12)	0.06334 (4)	0.01261 (14)
C14	0.74286 (8)	0.23932 (12)	0.08580 (4)	0.01396 (14)
H14A	0.7742	0.1113	0.0955	0.017*
C15	0.60318 (8)	0.29109 (12)	0.09343 (4)	0.01367 (14)
H15A	0.5381	0.1965	0.1079	0.016*
C16	0.16518 (8)	0.93989 (12)	0.07349 (4)	0.01381 (14)
H1O1	0.6599 (16)	0.855 (2)	0.0171 (7)	0.030 (4)*
H1N1	0.3969 (16)	0.791 (2)	0.0723 (7)	0.033 (4)*
H1O2	0.999 (2)	0.196 (3)	0.0635 (8)	0.052 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0131 (2)	0.0096 (2)	0.0195 (3)	0.00209 (19)	0.0036 (2)	0.0038 (2)
O2	0.0113 (2)	0.0159 (3)	0.0236 (3)	0.0048 (2)	0.0034 (2)	0.0040 (2)
O3	0.0129 (3)	0.0170 (3)	0.0299 (3)	0.0054 (2)	0.0033 (2)	0.0064 (2)
O4	0.0165 (3)	0.0150 (3)	0.0223 (3)	0.0018 (2)	0.0054 (2)	0.0063 (2)
N1	0.0109 (3)	0.0108 (3)	0.0150 (3)	0.0021 (2)	0.0019 (2)	0.0017 (2)
C1	0.0211 (4)	0.0189 (4)	0.0182 (4)	0.0017 (3)	−0.0009 (3)	0.0003 (3)
C2	0.0292 (5)	0.0244 (4)	0.0191 (4)	0.0075 (4)	−0.0044 (3)	0.0027 (3)
C3	0.0371 (5)	0.0170 (4)	0.0186 (4)	0.0083 (4)	0.0039 (4)	0.0047 (3)
C4	0.0267 (4)	0.0136 (3)	0.0207 (4)	0.0006 (3)	0.0076 (3)	0.0013 (3)
C5	0.0179 (4)	0.0155 (3)	0.0176 (4)	0.0011 (3)	0.0031 (3)	0.0011 (3)
C6	0.0165 (3)	0.0127 (3)	0.0137 (3)	0.0024 (3)	0.0043 (3)	0.0011 (3)
C7	0.0192 (4)	0.0125 (3)	0.0156 (3)	0.0028 (3)	0.0048 (3)	0.0018 (3)
C8	0.0104 (3)	0.0113 (3)	0.0160 (3)	0.0027 (2)	0.0022 (2)	0.0023 (2)
C9	0.0118 (3)	0.0110 (3)	0.0137 (3)	0.0016 (2)	0.0013 (2)	0.0010 (2)
C10	0.0102 (3)	0.0100 (3)	0.0135 (3)	0.0013 (2)	0.0013 (2)	0.0009 (2)
C11	0.0118 (3)	0.0098 (3)	0.0123 (3)	0.0016 (2)	0.0009 (2)	0.0002 (2)
C12	0.0108 (3)	0.0117 (3)	0.0162 (3)	0.0016 (2)	0.0015 (2)	0.0011 (3)
C13	0.0114 (3)	0.0129 (3)	0.0136 (3)	0.0029 (2)	0.0003 (2)	0.0007 (2)
C14	0.0129 (3)	0.0108 (3)	0.0182 (3)	0.0027 (2)	0.0014 (3)	0.0020 (3)
C15	0.0125 (3)	0.0107 (3)	0.0179 (3)	0.0013 (2)	0.0021 (2)	0.0022 (3)
C16	0.0136 (3)	0.0122 (3)	0.0157 (3)	0.0028 (2)	0.0017 (3)	0.0029 (3)

Geometric parameters (Å, º) top

O1—C11	1.3572 (9)	C5—H5A	0.9500
O1—H1O1	0.863 (15)	C6—C7	1.5068 (12)
O2—C13	1.3293 (10)	C7—C8	1.5461 (12)
O2—H1O2	1.025 (19)	C7—H7A	0.9900
O3—C16	1.2527 (10)	C7—H7B	0.9900
O4—C16	1.2577 (10)	C8—C16	1.5425 (11)
N1—C9	1.3045 (10)	C8—H8A	1.0000
N1—C8	1.4617 (10)	C9—C10	1.4220 (11)
N1—H1N1	0.864 (16)	C9—H9A	0.9500
C1—C2	1.3952 (13)	C10—C15	1.4152 (11)
C1—C6	1.3965 (12)	C10—C11	1.4220 (11)
C1—H1A	0.9500	C11—C12	1.3842 (11)
C2—C3	1.3863 (16)	C12—C13	1.4048 (11)
C2—H2A	0.9500	C12—H12A	0.9500
C3—C4	1.3921 (15)	C13—C14	1.4133 (11)
C3—H3A	0.9500	C14—C15	1.3745 (11)
C4—C5	1.3903 (13)	C14—H14A	0.9500
C4—H4A	0.9500	C15—H15A	0.9500
C5—C6	1.3973 (12)

C11—O1—H1O1	108.9 (10)	N1—C8—C7	111.03 (6)
C13—O2—H1O2	112.1 (10)	C16—C8—C7	107.65 (6)
C9—N1—C8	125.08 (7)	N1—C8—H8A	110.1
C9—N1—H1N1	120.3 (10)	C16—C8—H8A	110.1
C8—N1—H1N1	114.6 (10)	C7—C8—H8A	110.1
C2—C1—C6	120.37 (9)	N1—C9—C10	125.23 (7)
C2—C1—H1A	119.8	N1—C9—H9A	117.4
C6—C1—H1A	119.8	C10—C9—H9A	117.4
C3—C2—C1	120.51 (9)	C15—C10—C9	117.79 (7)
C3—C2—H2A	119.7	C15—C10—C11	118.13 (7)
C1—C2—H2A	119.7	C9—C10—C11	124.07 (7)
C2—C3—C4	119.53 (9)	O1—C11—C12	121.51 (7)
C2—C3—H3A	120.2	O1—C11—C10	117.88 (7)
C4—C3—H3A	120.2	C12—C11—C10	120.60 (7)
C5—C4—C3	120.06 (9)	C11—C12—C13	119.84 (7)
C5—C4—H4A	120.0	C11—C12—H12A	120.1
C3—C4—H4A	120.0	C13—C12—H12A	120.1
C4—C5—C6	120.90 (8)	O2—C13—C12	117.22 (7)
C4—C5—H5A	119.6	O2—C13—C14	122.24 (7)
C6—C5—H5A	119.6	C12—C13—C14	120.54 (7)
C1—C6—C5	118.64 (8)	C15—C14—C13	119.06 (7)
C1—C6—C7	121.20 (8)	C15—C14—H14A	120.5
C5—C6—C7	120.17 (8)	C13—C14—H14A	120.5
C6—C7—C8	114.68 (7)	C14—C15—C10	121.81 (7)
C6—C7—H7A	108.6	C14—C15—H15A	119.1
C8—C7—H7A	108.6	C10—C15—H15A	119.1
C6—C7—H7B	108.6	O3—C16—O4	127.87 (8)
C8—C7—H7B	108.6	O3—C16—C8	114.59 (7)
H7A—C7—H7B	107.6	O4—C16—C8	117.43 (7)
N1—C8—C16	107.91 (6)

C6—C1—C2—C3	0.53 (15)	C15—C10—C11—O1	178.38 (7)
C1—C2—C3—C4	−0.27 (15)	C9—C10—C11—O1	−1.95 (12)
C2—C3—C4—C5	−0.22 (15)	C15—C10—C11—C12	−1.04 (11)
C3—C4—C5—C6	0.45 (14)	C9—C10—C11—C12	178.63 (8)
C2—C1—C6—C5	−0.29 (13)	O1—C11—C12—C13	−178.40 (7)
C2—C1—C6—C7	179.02 (8)	C10—C11—C12—C13	1.00 (12)
C4—C5—C6—C1	−0.19 (13)	C11—C12—C13—O2	179.06 (7)
C4—C5—C6—C7	−179.51 (8)	C11—C12—C13—C14	−0.93 (12)
C1—C6—C7—C8	112.09 (9)	O2—C13—C14—C15	−179.07 (8)
C5—C6—C7—C8	−68.61 (10)	C12—C13—C14—C15	0.92 (12)
C9—N1—C8—C16	−166.85 (7)	C13—C14—C15—C10	−0.99 (13)
C9—N1—C8—C7	75.39 (10)	C9—C10—C15—C14	−178.64 (8)
C6—C7—C8—N1	−63.66 (9)	C11—C10—C15—C14	1.05 (12)
C6—C7—C8—C16	178.43 (7)	N1—C8—C16—O3	172.58 (7)
C8—N1—C9—C10	−175.36 (7)	C7—C8—C16—O3	−67.51 (9)
N1—C9—C10—C15	174.78 (8)	N1—C8—C16—O4	−10.87 (10)
N1—C9—C10—C11	−4.90 (13)	C7—C8—C16—O4	109.04 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O4ⁱ	0.863 (15)	1.790 (14)	2.6302 (9)	163.9 (15)
N1—H1N1···O1	0.864 (14)	2.051 (15)	2.6810 (9)	129.1 (12)
O2—H1O2···O3ⁱⁱ	1.03 (2)	1.51 (2)	2.5310 (10)	179 (2)
C5—H5A···O2ⁱⁱⁱ	0.95	2.56	3.3155 (10)	137
C12—H12A···O2^iv	0.95	2.46	3.1781 (10)	132

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅NO₄
M_r	285.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.3943 (1), 6.8946 (1), 20.7251 (3)
β (°)	92.065 (1)
V (Å³)	1341.49 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.34 × 0.27 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.966, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	22479, 6007, 4783
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.813

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.125, 1.03
No. of reflections	6007
No. of parameters	202
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.24

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
O1—H1O1···O4ⁱ	0.863 (15)	1.790 (14)	2.6302 (9)	163.9 (15)
N1—H1N1···O1	0.864 (14)	2.051 (15)	2.6810 (9)	129.1 (12)
O2—H1O2···O3ⁱⁱ	1.03 (2)	1.51 (2)	2.5310 (10)	179 (2)
C5—H5A···O2ⁱⁱⁱ	0.95	2.56	3.3155 (10)	137
C12—H12A···O2^iv	0.95	2.46	3.1781 (10)	132

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

Footnotes

‡Additional correspondence author, e-mail: hadariah@salam.uitm.edu.my.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HB, FMF and KK wish to thank both Universiti Teknologi MARA (UiTM) and Universiti Sains Malaysia (USM) for research facilities, and the Malaysian Ministry of Higher Education for the research grant FRGS UiTM 5/3/FST/(12/2008). HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

Bahron, H., Bakar, S. N. A., Kassim, K., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o883. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Dolaz, M., McKee, V., Golcu, A. & Tumer, M. (2009). Spectrochim. Acta Part A, 71, 1648–1654. CrossRef Google Scholar
Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o435–o436. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kumar, G., Kumar, D., Devi, S., Johari, R. & Singh, C. P. (2010). Eur. J. Med. Chem. 45, 3056–3062. Web of Science CrossRef CAS PubMed Google Scholar
Qiao, X., Ma, Z.-Y., Xie, C.-Z., Xue, F., Zhang, Y.-W., Xu, J.-Y., Qiang, Z.-Y., Lou, J.-S., Chen, G.-J. & Yan, S.-P. (2011). J. Inorg. Biochem. 105, 728–737. Web of Science CrossRef CAS PubMed Google Scholar
Sauri, A. S. M., Kassim, K., Bahron, H., Yahya, M. Z. A. & Harun, M. K. (2009). Mat. Res. Innovat. 13, 305–309. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tamami, B. & Ghasemi, S. (2011). Appl. Catal. A, 393, 242–250. CrossRef CAS Google Scholar