2-Methoxy­benzaldehyde 2,4-dinitro­phenyl­hydrazone

Fun, H.-K.; Kia, R.; Kargar, H.

doi:10.1107/S1600536809000038

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages o246-o247

doi:10.1107/S1600536809000038

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2-Methoxybenzaldehyde 2,4-dinitrophenylhydrazone

Hoong-Kun Fun,^a ^* Reza Kia ^a ‡ and Hadi Kargar ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran
^*Correspondence e-mail: hkfun@usm.my

(Received 4 December 2008; accepted 1 January 2009; online 8 January 2009)

In the title compound, C₁₄H₁₂N₄O₅, an intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. The dihedral angle between the two benzene rings is 3.91 (3)°, which shows the molecule is almost planar. The para-nitro group is twisted from the benzene ring to which it is attached, making a dihedral angle of 8.50 (9)°. In the crystal structure, molecules are linked together by intermolecular C—H⋯O and intermolecular three-centred O⋯O [2.8646 (12)–2.9213 (11) Å] and O⋯N [3.0518 (11) Å] interactions. The crystal structure is further stabilized by intermolecular π–π interactions [centroid-to-centroid distances 3.5708 (6)–3.9728 (12) Å].

Related literature

For general background, see: Lamberton et al. (1974 ); Zegota (1999 ); Cordis et al. (1998 ); Zlotorzynska & Lai (1999 ); Niknam et al. (2005 ); Guillaumont & Nakamura (2000 ); Raj & Kurup (2006 ). For biological applications, see: Okabe et al. (1993 ). Standard bond-length data are given in: Allen et al. (1987 ). For details of the classification of ring motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₂N₄O₅
M_r = 316.28
Triclinic, $[P \overline 1]$
a = 7.0315 (1) Å
b = 7.6205 (2) Å
c = 14.1896 (4) Å
α = 98.048 (1)°
β = 97.064 (1)°
γ = 109.467 (1)°
V = 697.99 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 100.0 (1) K
0.57 × 0.23 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.936, T_max = 0.988
14423 measured reflections
5023 independent reflections
4442 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.126
S = 1.06
5023 reflections
213 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2	0.864 (15)	2.029 (15)	2.6253 (11)	125.4 (13)
N2—H1N2⋯O2ⁱ	0.864 (15)	2.599 (15)	3.3475 (11)	145.6 (13)
C2—H2A⋯O4ⁱⁱ	0.93	2.44	3.3113 (12)	155
C5—H5A⋯O2ⁱⁱⁱ	0.93	2.60	3.3184 (11)	135
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x+1, y, z+1; (iii) x, y-1, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000038/pk2139sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809000038/pk2139Isup2.hkl

checkCIF report

Comment top

2,4-Dinitrophenylhydrazones play a more important role as stabilizers for the detection, characterization and protection of carbonyl groups than phenylhydrazones (Niknam et al., 2005). 2,4-Dinitrophenylhydrazone derivatives are widely used in various forms of analytical chemistry (Lamberton et al., 1974; Zegota, 1999; Cordis et al., 1998; Zlotorzynska & Lai, 1999) and are also used as dyes (Guillaumont & Nakamura, 2000). They are also found to have versatile coordinating abilities towards different metal ions (Raj & Kurup, 2006). In addition, some phenylhydrazone derivatives have been shown to be potentially DNA-damaging and mutagenic agents (Okabe et al., 1993). For these reasons, the structure of the title compound is reported here.

Bond lengths in the title compound (Fig. 1) are normal (Allen et al., 1987). An intramolecular N—H···O hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). The molecule is nearly planar, with a maximum deviation from the mean plane of -0.3464 (8) Å for atom O4 which is due to the intermolecular three-centered O···O and O···N interactions. The dihedral angle between the two benzene rings is 4.63 (1)°. Interesting features of the crystal structure include intermolecular three-centered O2···O2ⁱ [2.8646 (12) Å; (i) 1 - x, 1 - y, -z], O4···O4^iv [2.8646 (12) Å; (iv) code: -x, -y, -1 - z], and O4···N4ⁱⁱ [3.0518 (11) Å] interactions. The molecules are also linked by C—H···O hydrogen bonds (Table 1), and by intermolecular π–π interactions giving centroid–centroid distances for rings C1–C6 (Cg1) and C8–C13 (Cg2) of 3.5708 (6) Å and 3.9728 (12) Å [Cg1···Cg2^v; (v) -x, -y, -z and Cg1···Cg2^vi; (vi) 1 - x, -y, -z] (interplanar spacings are 3.3080 (4) and 3.3691 (4) Å respectively (Fig. 2).

Related literature top

For general background, see: Lamberton et al., (1974); Zegota, (1999); Cordis et al., (1998); Zlotorzynska & Lai, (1999); Niknam <i. et al. (2005); Guillaumont & Nakamura (2000); Raj & Kurup (2006). For the biological applications, see: Okabe et al. (1993). Standard bond-length data are given in: Allen et al. (1987). For details of the classification of ring motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized based on the reported procedure (Okabe et al. 1993) except that 3-methoxybenzaldehyde (1 mmol, 136 mg) was used instead. Single crystals suitable for X-ray diffraction analysis were grown by slow evaporation of a saturated solution of the resulted compound in ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering scheme. Hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound, viewed down the a axis, showing the molecules are linked through intermolecular C—H···O and O···O interactions and also are stacked along the a axis. Intermolecular interactions are shown as dashed lines.

2-Methoxybenzaldehyde 2,4-dinitrophenylhydrazone top

Crystal data top

C₁₄H₁₂N₄O₅	Z = 2
M_r = 316.28	F(000) = 328
Triclinic, P1	D_x = 1.505 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0315 (1) Å	Cell parameters from 6651 reflections
b = 7.6205 (2) Å	θ = 2.9–40.3°
c = 14.1896 (4) Å	µ = 0.12 mm⁻¹
α = 98.048 (1)°	T = 100 K
β = 97.064 (1)°	Block, orange
γ = 109.467 (1)°	0.57 × 0.23 × 0.10 mm
V = 697.99 (3) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5023 independent reflections
Radiation source: fine-focus sealed tube	4442 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 32.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
T_min = 0.936, T_max = 0.988	k = −11→11
14423 measured reflections	l = −21→21

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0683P)² + 0.1626P] where P = (F_o² + 2F_c²)/3
5023 reflections	(Δ/σ)_max < 0.001
213 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₄H₁₂N₄O₅	γ = 109.467 (1)°
M_r = 316.28	V = 697.99 (3) Å³
Triclinic, P1	Z = 2
a = 7.0315 (1) Å	Mo Kα radiation
b = 7.6205 (2) Å	µ = 0.12 mm⁻¹
c = 14.1896 (4) Å	T = 100 K
α = 98.048 (1)°	0.57 × 0.23 × 0.10 mm
β = 97.064 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5023 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4442 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.988	R_int = 0.021
14423 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.52 e Å⁻³
5023 reflections	Δρ_min = −0.25 e Å⁻³
213 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.52355 (11)	0.19077 (9)	0.30740 (5)	0.01789 (14)
O2	0.31793 (12)	0.47602 (10)	−0.06604 (5)	0.02132 (15)
O3	0.20422 (12)	0.51054 (10)	−0.20851 (5)	0.02350 (16)
O4	−0.18137 (11)	−0.00408 (11)	−0.45869 (5)	0.02104 (15)
O5	−0.19171 (12)	−0.28928 (10)	−0.44929 (5)	0.02410 (16)
N1	0.27092 (11)	0.00256 (11)	0.02604 (5)	0.01410 (14)
N2	0.26656 (12)	0.13732 (11)	−0.02830 (5)	0.01416 (14)
N3	0.22761 (12)	0.40930 (10)	−0.15138 (6)	0.01487 (15)
N4	−0.14093 (12)	−0.11921 (11)	−0.41450 (5)	0.01611 (15)
C1	0.46732 (13)	0.00043 (12)	0.27560 (6)	0.01377 (15)
C2	0.48758 (14)	−0.12628 (13)	0.33510 (6)	0.01710 (17)
H2A	0.5476	−0.0815	0.4001	0.021*
C3	0.41767 (15)	−0.31935 (14)	0.29676 (7)	0.01947 (18)
H3A	0.4306	−0.4035	0.3365	0.023*
C4	0.32856 (14)	−0.38821 (13)	0.19954 (7)	0.01804 (17)
H4A	0.2814	−0.5177	0.1745	0.022*
C5	0.31052 (13)	−0.26234 (12)	0.14015 (6)	0.01530 (16)
H5A	0.2514	−0.3085	0.0751	0.018*
C6	0.38009 (12)	−0.06701 (12)	0.17671 (6)	0.01284 (15)
C7	0.36703 (13)	0.06671 (12)	0.11394 (6)	0.01371 (15)
H7A	0.4276	0.1967	0.1373	0.016*
C8	0.17242 (12)	0.07996 (12)	−0.12228 (6)	0.01178 (15)
C9	0.09189 (13)	−0.11672 (12)	−0.16426 (6)	0.01378 (15)
H9A	0.1056	−0.2038	−0.1266	0.017*
C10	−0.00529 (13)	−0.18102 (12)	−0.25882 (6)	0.01405 (15)
H10A	−0.0547	−0.3101	−0.2852	0.017*
C11	−0.02975 (12)	−0.05112 (12)	−0.31553 (6)	0.01291 (15)
C12	0.04681 (12)	0.14065 (12)	−0.27956 (6)	0.01311 (15)
H12A	0.0307	0.2253	−0.3184	0.016*
C13	0.14893 (12)	0.20609 (11)	−0.18400 (6)	0.01222 (15)
C14	0.64623 (15)	0.27271 (14)	0.40200 (7)	0.01993 (18)
H14A	0.6876	0.4084	0.4120	0.030*
H14B	0.7657	0.2377	0.4074	0.030*
H14C	0.5675	0.2269	0.4500	0.030*
H1N2	0.329 (2)	0.256 (2)	−0.0027 (11)	0.035 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0227 (3)	0.0151 (3)	0.0117 (3)	0.0049 (2)	−0.0022 (2)	−0.0014 (2)
O2	0.0294 (4)	0.0137 (3)	0.0151 (3)	0.0053 (3)	−0.0036 (3)	−0.0028 (2)
O3	0.0317 (4)	0.0130 (3)	0.0239 (4)	0.0077 (3)	−0.0032 (3)	0.0055 (3)
O4	0.0218 (3)	0.0268 (4)	0.0147 (3)	0.0103 (3)	−0.0016 (2)	0.0048 (3)
O5	0.0274 (4)	0.0189 (3)	0.0185 (3)	0.0055 (3)	−0.0040 (3)	−0.0063 (3)
N1	0.0153 (3)	0.0149 (3)	0.0115 (3)	0.0049 (2)	0.0015 (2)	0.0030 (2)
N2	0.0173 (3)	0.0123 (3)	0.0109 (3)	0.0042 (3)	−0.0004 (2)	0.0014 (2)
N3	0.0162 (3)	0.0115 (3)	0.0158 (3)	0.0051 (2)	0.0007 (3)	0.0007 (2)
N4	0.0144 (3)	0.0190 (3)	0.0126 (3)	0.0052 (3)	−0.0001 (2)	−0.0002 (3)
C1	0.0130 (3)	0.0156 (4)	0.0116 (3)	0.0044 (3)	0.0017 (3)	0.0018 (3)
C2	0.0164 (4)	0.0212 (4)	0.0130 (4)	0.0057 (3)	0.0011 (3)	0.0049 (3)
C3	0.0199 (4)	0.0207 (4)	0.0195 (4)	0.0072 (3)	0.0041 (3)	0.0091 (3)
C4	0.0191 (4)	0.0142 (4)	0.0199 (4)	0.0042 (3)	0.0047 (3)	0.0040 (3)
C5	0.0151 (3)	0.0150 (4)	0.0136 (4)	0.0032 (3)	0.0024 (3)	0.0014 (3)
C6	0.0123 (3)	0.0145 (3)	0.0108 (3)	0.0040 (3)	0.0017 (3)	0.0018 (3)
C7	0.0145 (3)	0.0138 (3)	0.0118 (3)	0.0042 (3)	0.0019 (3)	0.0016 (3)
C8	0.0120 (3)	0.0124 (3)	0.0103 (3)	0.0042 (3)	0.0013 (3)	0.0010 (3)
C9	0.0160 (3)	0.0113 (3)	0.0128 (4)	0.0039 (3)	0.0015 (3)	0.0020 (3)
C10	0.0151 (3)	0.0111 (3)	0.0136 (4)	0.0030 (3)	0.0014 (3)	0.0001 (3)
C11	0.0119 (3)	0.0144 (3)	0.0103 (3)	0.0034 (3)	0.0000 (3)	0.0007 (3)
C12	0.0128 (3)	0.0139 (3)	0.0124 (3)	0.0051 (3)	0.0008 (3)	0.0022 (3)
C13	0.0128 (3)	0.0100 (3)	0.0129 (3)	0.0039 (3)	0.0007 (3)	0.0007 (3)
C14	0.0188 (4)	0.0225 (4)	0.0131 (4)	0.0048 (3)	−0.0019 (3)	−0.0032 (3)

Geometric parameters (Å, º) top

O1—C1	1.3618 (11)	C4—C5	1.3883 (13)
O1—C14	1.4344 (11)	C4—H4A	0.9300
O2—N3	1.2456 (10)	C5—C6	1.4001 (12)
O3—N3	1.2274 (10)	C5—H5A	0.9300
O4—N4	1.2329 (10)	C6—C7	1.4617 (12)
O5—N4	1.2328 (10)	C7—H7A	0.9300
N1—C7	1.2858 (11)	C8—C9	1.4224 (11)
N1—N2	1.3736 (10)	C8—C13	1.4227 (11)
N2—C8	1.3545 (10)	C9—C10	1.3692 (11)
N2—H1N2	0.864 (16)	C9—H9A	0.9300
N3—C13	1.4435 (11)	C10—C11	1.3998 (12)
N4—C11	1.4520 (11)	C10—H10A	0.9300
C1—C2	1.3985 (12)	C11—C12	1.3730 (12)
C1—C6	1.4092 (11)	C12—C13	1.3912 (11)
C2—C3	1.3894 (14)	C12—H12A	0.9300
C2—H2A	0.9300	C14—H14A	0.9600
C3—C4	1.3916 (13)	C14—H14B	0.9600
C3—H3A	0.9300	C14—H14C	0.9600

C1—O1—C14	118.36 (7)	C1—C6—C7	119.95 (7)
C7—N1—N2	115.65 (7)	N1—C7—C6	119.25 (8)
C8—N2—N1	118.87 (7)	N1—C7—H7A	120.4
C8—N2—H1N2	121.6 (10)	C6—C7—H7A	120.4
N1—N2—H1N2	119.4 (10)	N2—C8—C9	119.67 (7)
O3—N3—O2	122.20 (7)	N2—C8—C13	123.82 (7)
O3—N3—C13	119.09 (7)	C9—C8—C13	116.51 (7)
O2—N3—C13	118.71 (7)	C10—C9—C8	121.61 (8)
O5—N4—O4	123.66 (8)	C10—C9—H9A	119.2
O5—N4—C11	118.19 (7)	C8—C9—H9A	119.2
O4—N4—C11	118.15 (7)	C9—C10—C11	119.52 (8)
O1—C1—C2	123.98 (8)	C9—C10—H10A	120.2
O1—C1—C6	115.86 (7)	C11—C10—H10A	120.2
C2—C1—C6	120.14 (8)	C12—C11—C10	121.62 (8)
C3—C2—C1	119.74 (8)	C12—C11—N4	118.64 (7)
C3—C2—H2A	120.1	C10—C11—N4	119.74 (7)
C1—C2—H2A	120.1	C11—C12—C13	118.80 (8)
C2—C3—C4	120.73 (8)	C11—C12—H12A	120.6
C2—C3—H3A	119.6	C13—C12—H12A	120.6
C4—C3—H3A	119.6	C12—C13—C8	121.90 (7)
C5—C4—C3	119.58 (8)	C12—C13—N3	115.84 (7)
C5—C4—H4A	120.2	C8—C13—N3	122.26 (7)
C3—C4—H4A	120.2	O1—C14—H14A	109.5
C4—C5—C6	120.96 (8)	O1—C14—H14B	109.5
C4—C5—H5A	119.5	H14A—C14—H14B	109.5
C6—C5—H5A	119.5	O1—C14—H14C	109.5
C5—C6—C1	118.84 (8)	H14A—C14—H14C	109.5
C5—C6—C7	121.21 (7)	H14B—C14—H14C	109.5

C7—N1—N2—C8	178.35 (7)	C13—C8—C9—C10	−0.77 (12)
C14—O1—C1—C2	12.61 (13)	C8—C9—C10—C11	−1.15 (13)
C14—O1—C1—C6	−168.81 (8)	C9—C10—C11—C12	1.96 (13)
O1—C1—C2—C3	177.25 (8)	C9—C10—C11—N4	−177.18 (8)
C6—C1—C2—C3	−1.27 (13)	O5—N4—C11—C12	173.05 (8)
C1—C2—C3—C4	0.36 (14)	O4—N4—C11—C12	−7.77 (12)
C2—C3—C4—C5	0.38 (14)	O5—N4—C11—C10	−7.78 (12)
C3—C4—C5—C6	−0.21 (14)	O4—N4—C11—C10	171.39 (8)
C4—C5—C6—C1	−0.69 (13)	C10—C11—C12—C13	−0.75 (13)
C4—C5—C6—C7	178.17 (8)	N4—C11—C12—C13	178.40 (7)
O1—C1—C6—C5	−177.21 (7)	C11—C12—C13—C8	−1.28 (13)
C2—C1—C6—C5	1.43 (13)	C11—C12—C13—N3	179.24 (7)
O1—C1—C6—C7	3.91 (12)	N2—C8—C13—C12	−178.46 (8)
C2—C1—C6—C7	−177.45 (8)	C9—C8—C13—C12	2.01 (12)
N2—N1—C7—C6	−179.67 (7)	N2—C8—C13—N3	0.98 (13)
C5—C6—C7—N1	7.29 (13)	C9—C8—C13—N3	−178.55 (7)
C1—C6—C7—N1	−173.86 (8)	O3—N3—C13—C12	−1.30 (12)
N1—N2—C8—C9	−3.93 (12)	O2—N3—C13—C12	178.99 (8)
N1—N2—C8—C13	176.55 (8)	O3—N3—C13—C8	179.23 (8)
N2—C8—C9—C10	179.68 (8)	O2—N3—C13—C8	−0.48 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2	0.864 (15)	2.029 (15)	2.6253 (11)	125.4 (13)
N2—H1N2···O2ⁱ	0.864 (15)	2.599 (15)	3.3475 (11)	145.6 (13)
C2—H2A···O4ⁱⁱ	0.93	2.44	3.3113 (12)	155
C5—H5A···O2ⁱⁱⁱ	0.93	2.60	3.3184 (11)	135

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂N₄O₅
M_r	316.28
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.0315 (1), 7.6205 (2), 14.1896 (4)
α, β, γ (°)	98.048 (1), 97.064 (1), 109.467 (1)
V (Å³)	697.99 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.57 × 0.23 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.936, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	14423, 5023, 4442
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.126, 1.06
No. of reflections	5023
No. of parameters	213
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.25

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2	0.864 (15)	2.029 (15)	2.6253 (11)	125.4 (13)
N2—H1N2···O2ⁱ	0.864 (15)	2.599 (15)	3.3475 (11)	145.6 (13)
C2—H2A···O4ⁱⁱ	0.9300	2.4400	3.3113 (12)	155.00
C5—H5A···O2ⁱⁱⁱ	0.9300	2.6000	3.3184 (11)	135.00

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

Footnotes

‡Additional correspondence author: e-mail: zsrkk@yahoo.com.

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. RK thanks the Universiti Sains Malaysia for awarding a postdoctoral research fellowship. HK thanks PNU for financial support of this work.

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