N′-[(E)-2,3-Dihy­droxy­benzyl­idene]-2-meth­oxy­benzohydrazide

Taha, M.; Baharudin, M.S.; Ismail, N.H.; Shah, S.A.A.; Yousuf, S.

doi:10.1107/S1600536812042390

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3256

doi:10.1107/S1600536812042390

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N′-[(E)-2,3-Dihydroxybenzylidene]-2-methoxybenzohydrazide

Muhammad Taha,^a M. Syukri. Baharudin,^a Nor Hadiani Ismail,^b Syed Adnan Ali Shah ^a,^c and Sammer Yousuf ^d ^*

^aAtta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor D. E. Malaysia, ^bFaculty of Applied Science, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Malaysia, ^cFaculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam, 42300, Selangor, Malaysia, and ^dH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
^*Correspondence e-mail: dr.sammer.yousuf@gmail.com

(Received 5 October 2012; accepted 10 October 2012; online 3 November 2012)

The title compound, C₁₅H₁₄N₂O₄ adopts an E conformation about the azomethine double bond. Intramolecular N—H⋯O and O—H⋯N hydrogen bonds generate S(6) rings and help to establish the molecular conformation. The dihedral angle between the benzene rings is 17.84 (10)°. In the crystal, molecules are linked by O—H⋯O and C—H⋯O hydrogen bonds into a two-dimensional network with a herring-bone pattern arranged parallel to the bc plane.

Related literature

For applications and the biological activity of Schiff bases, see: Panneerselvam et al. (2009 ); Khan et al. (2009 ); Jarahpour et al. (2007 ). For related structures, see: Baharudin et al. (2012 ); Taha et al. (2012 ); Promdet et al. (2011 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₄
M_r = 286.28
Orthorhombic, P b c a
a = 14.1479 (17) Å
b = 8.6567 (11) Å
c = 22.570 (3) Å
V = 2764.2 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 K
0.56 × 0.18 × 0.04 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.945, T_max = 0.996
15288 measured reflections
2574 independent reflections
1658 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.115
S = 1.03
2574 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.91 (2)	1.90 (2)	2.608 (2)	133 (2)
O3—H3A⋯O1ⁱ	0.90 (3)	1.75 (3)	2.631 (2)	167 (2)
O4—H4A⋯N2	0.85 (2)	1.89 (2)	2.658 (2)	151 (2)
C8—H8A⋯O3ⁱⁱ	0.93	2.33	3.189 (2)	153
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812042390/pv2594sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812042390/pv2594Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812042390/pv2594Isup3.cml

checkCIF report

Comment top

Schiff bases represent an important group of organic compounds with a wide range of medicinal applications (Panneerselvam et al., 2009; Khan et al., 2009; Jarahpour et al., 2007). The title Schiff base was synthesize as a part of our ongoing resaerch to study different bioactive organic compounds.

The bond lengths and angle in the title compound (Fig. 1) are similar to the corresponding bond lengths and bond angles reported in structurally realted Schiff bases (Taha et al., 2012; Promdet et al., 2011). The E configuration of azomethine oelfinic bond is stabilized by two intramolecular N1—H1A···O2, O4—H4A···N2 hydrogen bonds. O3—H3A···O1 and C8—H8A···O3 hydrogen bonds play important roles in stabilizing the crystal structure by forming a two-dimensional-network arranged parallel to the bc plane in a zig zag fashion (Table 2 and Fig. 2).

Related literature top

For applications and the biological activity of Schiff bases, see: Panneerselvam et al. (2009); Khan et al. (2009); Jarahpour et al. (2007). For related structures, see: Baharudin et al. (2012); Taha et al. (2012); Promdet et al. (2011).

Experimental top

The title compound was synthesized by refluxing a mixture of 2-methoxybenzohydrazide (0.332 g, 2 mmol) and 2,3-dihydroxybenzaldehyde (0.276 g, 2 mmol) in methanol (40 ml) along with a catalytical amount of acetic acid for 3 hr. The progress of reaction was monitored by TLC. After completion of reaction, the solvent was evaporated under reduced vacuum to afford crude product which was recrystallized by dissolving in methanol at room temperature to obtain pure needles (0.458 g, 80% yield). All chemicals were purchased by sigma Aldrich Germany.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom numbering scheme and N—-H···O and O—H···N intramolecular hydrogen bonds (dotted lines). Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the O—-H···O and C—H···O hydrogen bonds (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity.

N'-[(E)-2,3-Dihydroxybenzylidene]-2-methoxybenzohydrazide top

Crystal data top

C₁₅H₁₄N₂O₄	F(000) = 1200
M_r = 286.28	D_x = 1.376 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1873 reflections
a = 14.1479 (17) Å	θ = 2.9–22.2°
b = 8.6567 (11) Å	µ = 0.10 mm⁻¹
c = 22.570 (3) Å	T = 273 K
V = 2764.2 (6) Å³	Plate, colorles
Z = 8	0.56 × 0.18 × 0.04 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2574 independent reflections
Radiation source: fine-focus sealed tube	1658 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scan	θ_max = 25.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −15→17
T_min = 0.945, T_max = 0.996	k = −10→10
15288 measured reflections	l = −27→26

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.050P)² + 0.1101P] where P = (F_o² + 2F_c²)/3
2574 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₄	V = 2764.2 (6) Å³
M_r = 286.28	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.1479 (17) Å	µ = 0.10 mm⁻¹
b = 8.6567 (11) Å	T = 273 K
c = 22.570 (3) Å	0.56 × 0.18 × 0.04 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2574 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1658 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.996	R_int = 0.042
15288 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.14 e Å⁻³
2574 reflections	Δρ_min = −0.15 e Å⁻³
203 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.

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	0.14939 (10)	−0.02998 (18)	0.40701 (6)	0.0774 (5)
O2	0.43755 (10)	−0.00963 (18)	0.38297 (7)	0.0813 (5)
O3	−0.04853 (10)	0.35880 (19)	0.18114 (7)	0.0812 (5)
H3A	−0.0756 (18)	0.407 (3)	0.1500 (12)	0.124 (11)*
O4	0.04345 (10)	0.21110 (17)	0.26425 (7)	0.0705 (4)
H4A	0.0826 (17)	0.178 (3)	0.2896 (11)	0.106 (9)*
N1	0.26779 (14)	0.08816 (19)	0.35803 (7)	0.0591 (5)
H1A	0.3313 (16)	0.098 (3)	0.3523 (9)	0.087 (8)*
N2	0.20663 (11)	0.16136 (18)	0.31942 (7)	0.0569 (4)
C1	0.26911 (17)	−0.1677 (2)	0.48710 (9)	0.0752 (6)
H1B	0.2044	−0.1659	0.4943	0.090*
C2	0.3267 (2)	−0.2513 (3)	0.52416 (10)	0.0900 (7)
H2B	0.3011	−0.3049	0.5560	0.108*
C3	0.4220 (2)	−0.2550 (3)	0.51384 (11)	0.0924 (8)
H3B	0.4611	−0.3115	0.5389	0.111*
C4	0.46035 (17)	−0.1762 (3)	0.46702 (10)	0.0793 (7)
H4B	0.5252	−0.1801	0.4603	0.095*
C5	0.40271 (15)	−0.0908 (2)	0.42963 (9)	0.0628 (5)
C6	0.30501 (15)	−0.0859 (2)	0.43918 (8)	0.0575 (5)
C7	0.23441 (15)	−0.0071 (2)	0.40039 (8)	0.0576 (5)
C8	0.24524 (13)	0.2483 (2)	0.28070 (8)	0.0572 (5)
H8A	0.3106	0.2591	0.2809	0.069*
C9	0.19093 (12)	0.3307 (2)	0.23652 (8)	0.0498 (5)
C10	0.23670 (14)	0.4340 (2)	0.19876 (8)	0.0623 (5)
H10A	0.3015	0.4492	0.2026	0.075*
C11	0.18796 (15)	0.5134 (2)	0.15615 (9)	0.0661 (6)
H11A	0.2194	0.5829	0.1317	0.079*
C12	0.09193 (14)	0.4901 (2)	0.14946 (8)	0.0585 (5)
H12A	0.0588	0.5437	0.1204	0.070*
C13	0.04530 (13)	0.3880 (2)	0.18569 (8)	0.0532 (5)
C14	0.09401 (12)	0.3093 (2)	0.23002 (7)	0.0494 (5)
C15	0.53330 (16)	−0.0285 (3)	0.36517 (11)	0.0872 (7)
H15A	0.5444	0.0292	0.3295	0.131*
H15B	0.5458	−0.1359	0.3581	0.131*
H15C	0.5743	0.0086	0.3959	0.131*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0578 (10)	0.1019 (12)	0.0724 (10)	−0.0083 (8)	−0.0062 (7)	−0.0100 (8)
O2	0.0576 (10)	0.0926 (11)	0.0937 (11)	0.0069 (8)	0.0005 (8)	0.0279 (9)
O3	0.0449 (9)	0.1000 (12)	0.0987 (12)	−0.0024 (7)	−0.0091 (8)	0.0351 (10)
O4	0.0515 (9)	0.0821 (10)	0.0779 (10)	−0.0071 (7)	0.0010 (7)	0.0256 (8)
N1	0.0526 (11)	0.0636 (11)	0.0611 (10)	0.0055 (9)	−0.0122 (9)	−0.0064 (9)
N2	0.0563 (10)	0.0587 (10)	0.0558 (10)	0.0057 (8)	−0.0112 (8)	−0.0083 (8)
C1	0.0884 (17)	0.0784 (15)	0.0588 (13)	−0.0058 (13)	0.0001 (12)	−0.0060 (12)
C2	0.123 (2)	0.0840 (17)	0.0635 (15)	0.0011 (17)	−0.0016 (15)	0.0123 (13)
C3	0.120 (2)	0.0834 (17)	0.0741 (16)	0.0164 (17)	−0.0178 (15)	0.0069 (14)
C4	0.0828 (17)	0.0764 (15)	0.0787 (15)	0.0075 (12)	−0.0191 (13)	0.0026 (14)
C5	0.0692 (15)	0.0594 (12)	0.0597 (12)	−0.0002 (11)	−0.0112 (11)	−0.0026 (11)
C6	0.0672 (14)	0.0543 (11)	0.0512 (12)	−0.0023 (10)	−0.0087 (10)	−0.0108 (10)
C7	0.0594 (14)	0.0605 (12)	0.0528 (12)	−0.0033 (10)	−0.0059 (10)	−0.0153 (10)
C8	0.0467 (11)	0.0611 (11)	0.0638 (12)	−0.0008 (10)	−0.0078 (10)	−0.0143 (11)
C9	0.0457 (11)	0.0503 (10)	0.0533 (11)	−0.0015 (8)	0.0004 (8)	−0.0113 (9)
C10	0.0489 (12)	0.0679 (13)	0.0700 (13)	−0.0115 (10)	0.0054 (10)	−0.0082 (11)
C11	0.0723 (14)	0.0613 (13)	0.0648 (13)	−0.0153 (11)	0.0126 (11)	0.0012 (11)
C12	0.0644 (13)	0.0547 (11)	0.0565 (11)	0.0022 (10)	0.0021 (10)	0.0014 (10)
C13	0.0439 (11)	0.0541 (11)	0.0616 (12)	0.0017 (9)	0.0016 (9)	0.0011 (10)
C14	0.0465 (11)	0.0487 (10)	0.0531 (11)	−0.0023 (8)	0.0063 (9)	−0.0007 (9)
C15	0.0601 (15)	0.0902 (17)	0.1112 (19)	0.0038 (12)	0.0052 (13)	0.0059 (15)

Geometric parameters (Å, º) top

O1—C7	1.228 (2)	C4—C5	1.387 (3)
O2—C5	1.359 (2)	C4—H4B	0.9300
O2—C15	1.422 (2)	C5—C6	1.400 (3)
O3—C13	1.355 (2)	C6—C7	1.493 (3)
O3—H3A	0.90 (3)	C8—C9	1.447 (2)
O4—C14	1.353 (2)	C8—H8A	0.9300
O4—H4A	0.85 (2)	C9—C14	1.392 (2)
N1—C7	1.348 (2)	C9—C10	1.395 (2)
N1—N2	1.382 (2)	C10—C11	1.368 (3)
N1—H1A	0.91 (2)	C10—H10A	0.9300
N2—C8	1.276 (2)	C11—C12	1.382 (3)
C1—C2	1.373 (3)	C11—H11A	0.9300
C1—C6	1.389 (3)	C12—C13	1.373 (2)
C1—H1B	0.9300	C12—H12A	0.9300
C2—C3	1.368 (3)	C13—C14	1.393 (2)
C2—H2B	0.9300	C15—H15A	0.9600
C3—C4	1.370 (3)	C15—H15B	0.9600
C3—H3B	0.9300	C15—H15C	0.9600

C5—O2—C15	120.34 (17)	N2—C8—C9	122.37 (17)
C13—O3—H3A	113.0 (17)	N2—C8—H8A	118.8
C14—O4—H4A	104.7 (17)	C9—C8—H8A	118.8
C7—N1—N2	120.55 (18)	C14—C9—C10	118.61 (17)
C7—N1—H1A	120.2 (14)	C14—C9—C8	122.01 (16)
N2—N1—H1A	119.1 (14)	C10—C9—C8	119.38 (17)
C8—N2—N1	115.74 (17)	C11—C10—C9	121.16 (19)
C2—C1—C6	121.7 (2)	C11—C10—H10A	119.4
C2—C1—H1B	119.1	C9—C10—H10A	119.4
C6—C1—H1B	119.1	C10—C11—C12	119.95 (18)
C3—C2—C1	119.5 (2)	C10—C11—H11A	120.0
C3—C2—H2B	120.2	C12—C11—H11A	120.0
C1—C2—H2B	120.2	C13—C12—C11	120.08 (18)
C2—C3—C4	120.7 (2)	C13—C12—H12A	120.0
C2—C3—H3B	119.7	C11—C12—H12A	120.0
C4—C3—H3B	119.7	O3—C13—C12	123.07 (17)
C3—C4—C5	120.1 (2)	O3—C13—C14	116.58 (17)
C3—C4—H4B	119.9	C12—C13—C14	120.34 (17)
C5—C4—H4B	119.9	O4—C14—C9	123.01 (16)
O2—C5—C4	122.3 (2)	O4—C14—C13	117.13 (16)
O2—C5—C6	117.50 (17)	C9—C14—C13	119.84 (16)
C4—C5—C6	120.2 (2)	O2—C15—H15A	109.5
C1—C6—C5	117.72 (19)	O2—C15—H15B	109.5
C1—C6—C7	116.4 (2)	H15A—C15—H15B	109.5
C5—C6—C7	125.77 (19)	O2—C15—H15C	109.5
O1—C7—N1	121.88 (19)	H15A—C15—H15C	109.5
O1—C7—C6	120.7 (2)	H15B—C15—H15C	109.5
N1—C7—C6	117.45 (19)

C7—N1—N2—C8	−179.58 (16)	C5—C6—C7—N1	−11.4 (3)
C6—C1—C2—C3	−0.2 (3)	N1—N2—C8—C9	178.90 (14)
C1—C2—C3—C4	0.0 (4)	N2—C8—C9—C14	−6.0 (3)
C2—C3—C4—C5	0.4 (4)	N2—C8—C9—C10	174.56 (16)
C15—O2—C5—C4	9.8 (3)	C14—C9—C10—C11	0.1 (3)
C15—O2—C5—C6	−170.20 (18)	C8—C9—C10—C11	179.55 (16)
C3—C4—C5—O2	179.4 (2)	C9—C10—C11—C12	−0.9 (3)
C3—C4—C5—C6	−0.6 (3)	C10—C11—C12—C13	0.3 (3)
C2—C1—C6—C5	−0.1 (3)	C11—C12—C13—O3	−179.38 (18)
C2—C1—C6—C7	176.70 (19)	C11—C12—C13—C14	1.1 (3)
O2—C5—C6—C1	−179.52 (17)	C10—C9—C14—O4	179.63 (16)
C4—C5—C6—C1	0.5 (3)	C8—C9—C14—O4	0.2 (3)
O2—C5—C6—C7	4.1 (3)	C10—C9—C14—C13	1.2 (2)
C4—C5—C6—C7	−175.94 (17)	C8—C9—C14—C13	−178.16 (16)
N2—N1—C7—O1	−1.4 (3)	O3—C13—C14—O4	0.1 (2)
N2—N1—C7—C6	178.09 (14)	C12—C13—C14—O4	179.65 (16)
C1—C6—C7—O1	−8.4 (3)	O3—C13—C14—C9	178.57 (16)
C5—C6—C7—O1	168.06 (18)	C12—C13—C14—C9	−1.9 (3)
C1—C6—C7—N1	172.13 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.91 (2)	1.90 (2)	2.608 (2)	133 (2)
O3—H3A···O1ⁱ	0.90 (3)	1.75 (3)	2.631 (2)	167 (2)
O4—H4A···N2	0.85 (2)	1.89 (2)	2.658 (2)	151 (2)
C8—H8A···O3ⁱⁱ	0.93	2.33	3.189 (2)	153

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₄
M_r	286.28
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	273
a, b, c (Å)	14.1479 (17), 8.6567 (11), 22.570 (3)
V (Å³)	2764.2 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.56 × 0.18 × 0.04

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.945, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	15288, 2574, 1658
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.115, 1.03
No. of reflections	2574
No. of parameters	203
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.15

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.91 (2)	1.90 (2)	2.608 (2)	133 (2)
O3—H3A···O1ⁱ	0.90 (3)	1.75 (3)	2.631 (2)	167 (2)
O4—H4A···N2	0.85 (2)	1.89 (2)	2.658 (2)	151 (2)
C8—H8A···O3ⁱⁱ	0.93	2.33	3.189 (2)	152.6

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

References

Baharudin, M. S., Taha, M., Ismail, N. H., Shah, S. A. A. & Yousuf, S. (2012). Acta Cryst. E68, o3255. CSD CrossRef IUCr Journals Google Scholar
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jarahpour, A., Khalili, D., De Clercq, E., Salmi, C. & Brunel, J. M. (2007). Molecules. 12, 1720–1730. Web of Science PubMed Google Scholar
Khan, K. M., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 7795–7801. Web of Science CrossRef PubMed CAS Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Panneerselvam, P., Rather, B. A., Reddy, D. R. S. & Kumar, R. N. (2009). Eur. J. Med. Chem. 44, 2328–2333. Web of Science CrossRef PubMed CAS Google Scholar
Promdet, P., Horkaew, J., Chantrapromma, S. & Fun, H.-K. (2011). Acta Cryst. E67, o3224. Web of Science CSD CrossRef IUCr Journals 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
Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Yousuf, S. (2012). Acta Cryst. E68, o2846. CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 12| December 2012| Page o3256

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