(E)-1-(2,4-Dinitro­phen­yl)-2-[1-(thio­phen-2-yl)ethyl­idene]hydrazine

Fun, H.-K.; Jansrisewangwong, P.; Chantrapromma, S.

doi:10.1107/S1600536811011135

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1034-o1035

doi:10.1107/S1600536811011135

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(E)-1-(2,4-Dinitrophenyl)-2-[1-(thiophen-2-yl)ethylidene]hydrazine

Hoong-Kun Fun,^a ^*‡ Patcharaporn Jansrisewangwong ^b and Suchada Chantrapromma ^b §

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 14 March 2011; accepted 25 March 2011; online 7 April 2011)

The molecule of the title compound, C₁₂H₁₀N₄O₄S, is slightly twisted, with a dihedral angle of 8.23 (9)° between the benzene and thiophene rings. One nitro group is co-planar [O—N—C—C torsion angles = −0.5 (3) and −1.9 (3)°] whereas the other is slightly twisted with respect to the benzene ring [O—N—C—C torsion angles = −5.1 (3) and −5.7 (3)°]. In the crystal, the molecules are linked by weak C—H⋯O interactions into screw chains along the b axis. The molecular conformation is consolidated by an intramolecular N—H⋯O hydrogen bond.

Related literature

For bond-length data, see: Allen et al. (1987 ). For related structures, see: Chantrapromma et al. (2010 ); Fun et al. (2010 ); Jansrisewangwong et al. (2010 ); Shan et al. (2008 ). For background to and the biological activity of hydrazones, see: Baughman et al. (2004 ); Bedia et al. (2006 ); El-Tabl et al. (2008); Ramamohan et al. (1995 ); Rollas & Küçükgüzel (2007 ). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₂H₁₀N₄O₄S
M_r = 306.30
Monoclinic, P 2₁ /c
a = 9.4868 (5) Å
b = 15.3912 (8) Å
c = 8.9756 (4) Å
β = 91.672 (2)°
V = 1310.00 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 K
0.60 × 0.19 × 0.16 mm

Data collection

Bruker APEXII CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.854, T_max = 0.959
10366 measured reflections
2414 independent reflections
2176 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.109
S = 1.08
2414 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1	0.79 (3)	2.00 (3)	2.618 (3)	134 (2)
C6—H6A⋯O2ⁱ	0.93	2.45	3.099 (3)	127
C9—H9A⋯O4ⁱⁱ	0.93	2.47	3.147 (2)	129
C11—H11A⋯O3ⁱ	0.93	2.57	3.240 (3)	129
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x-1, y, z+1.

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/S1600536811011135/rz2573sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011135/rz2573Isup2.hkl

checkCIF report

Comment top

Hydrazones are an important class of compounds which are used in numerous biological and pharmacological applications as insecticidal, antitumor, antioxidant, antifungal, antibacterial, antiviral and antituberculosis compounds (Bedia et al., 2006; El-Tabl et al., 2008; Ramamohan et al., 1995; Rollas & Küçükgüzel, 2007). Several of them also exhibit good nonlinear optical properties (Baughman et al., 2004). In our previous studies we reported the syntheses and crystal structures of some hydrazone derivatives (Chantrapromma et al., 2010; Fun et al., 2010; Jansrisewangwong et al., 2010). The title compound (I) was synthesized as part of our on going research on biological activities of hydrazones.

The molecule of (I), (Fig. 1), is slightly twisted with the dihedral angle between the benzene and thiophene rings of 8.23 (9)°. The middle ethylidinehydrazine unit (N1/N2/C7/C12) is planar with the r.m.s. 0.0033 (2) Å and the torsion angle N2–N1–C7–C12 = -1.1 (3)°. This N—N=C—C bridge makes dihedral angles of 6.62 (11) and 2.14 (12)° with the benzene and thiophene rings, respectively. The nitro group at atom C2 is co-planar [torsion angles O1–N3–C2–C1 = -0.5 (3)° and O2–N3–C2–C3 = -1.9 (3)°] whereby that at atom C4 is slightly twisted with respect to the benzene ring [torsion angles O3–N4–C4–C3 = -5.1 (3)° and O4–N4–C4–C5 = -5.7 (3)°]. The bond distances are of normal values (Allen et al., 1987) and comparable with those found in related structures (Jansrisewangwong et al., 2010; Shan et al., 2008).

In the crystal structure (Fig. 2), the molecules are linked by C—H···O weak interactions (Table 1) into screw chains along the b axis. The molecular conformation is consolidated by an intramolecular N—H···O hydrogen bonding interaction (Table 1). C···N^{iii, iv}[3.219 (3)–3.232 (3) Å], C···O^{iii, v,vi}[3.099 (3)–3.187 (2) Å] and N···O^vii[2.971 (2) Å] short contacts are also observed [symmetry codes: (iii) x, 1/2 - y, -1/2 + z; (iv) 1 + x, 1/2 - y, -1/2 + z; (v) 1 - x, 1/2 + y, 3/2 - z; (vi) 1 + x, y, -1 + z and (vii) 1 - x, 1 - y, 2 - z].

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures, see: Chantrapromma et al. (2010); Fun et al. (2010); Jansrisewangwong et al. (2010); Shan et al. (2008). For background to and the biological activity of hydrazones, see: Baughman et al. (2004); Bedia et al. (2006); El-Tabl et al. (2008); Ramamohan et al. (1995); Rollas & Küçükgüzel (2007). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986).

Experimental top

The title compound was synthesized by dissolving 2,4-dinitrophenylhydrazine (0.40 g, 2 mmol) in ethanol (10 ml) and H₂SO₄ (conc.) (98%, 0.5 ml) was slowly added with stirring. Then 2-acetylthiophene (0.20 ml, 2 mmol) was added to the solution with continuous stirring. The solution was refluxed for 30 min yielding an orange-red solid, which was filtered off and washed with methanol. Orange block-shaped single crystals of the title compound suitable for X-ray structure determination were recrystalized from ethanol by slow evaporation of the solvent at room temperature over several days. Mp. 516–518 K.

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 molecular structure of the title compound, showing 50% probability displacement ellipsoids. The intramolecular hydrogen bond is drawn as dash line.
	Fig. 2. The crystal packing of the title compound viewed along the c axis. Hydrogen bonds are drawn as dashed lines.

(E)-1-(2,4-Dinitrophenyl)-2-[1-(thiophen-2-yl)ethylidene]hydrazine top

Crystal data top

C₁₂H₁₀N₄O₄S	F(000) = 632
M_r = 306.30	D_x = 1.553 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 516–518 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.4868 (5) Å	Cell parameters from 2414 reflections
b = 15.3912 (8) Å	θ = 2.2–25.5°
c = 8.9756 (4) Å	µ = 0.27 mm⁻¹
β = 91.672 (2)°	T = 100 K
V = 1310.00 (11) Å³	Block, orange
Z = 4	0.60 × 0.19 × 0.16 mm

Data collection top

Bruker APEXII CCD area detector diffractometer	2414 independent reflections
Radiation source: sealed tube	2176 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→11
T_min = 0.854, T_max = 0.959	k = −18→14
10366 measured reflections	l = −10→10

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0504P)² + 1.3252P] where P = (F_o² + 2F_c²)/3
2414 reflections	(Δ/σ)_max < 0.001
195 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₂H₁₀N₄O₄S	V = 1310.00 (11) Å³
M_r = 306.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4868 (5) Å	µ = 0.27 mm⁻¹
b = 15.3912 (8) Å	T = 100 K
c = 8.9756 (4) Å	0.60 × 0.19 × 0.16 mm
β = 91.672 (2)°

Data collection top

Bruker APEXII CCD area detector diffractometer	2414 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2176 reflections with I > 2σ(I)
T_min = 0.854, T_max = 0.959	R_int = 0.027
10366 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.38 e Å⁻³
2414 reflections	Δρ_min = −0.44 e Å⁻³
195 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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
S1	0.18528 (6)	0.07603 (4)	1.08312 (6)	0.02114 (18)
O1	0.38055 (16)	0.48642 (10)	0.89817 (17)	0.0234 (4)
O2	0.5358 (2)	0.53354 (10)	0.7464 (2)	0.0367 (5)
O3	0.82477 (16)	0.34691 (11)	0.46978 (17)	0.0263 (4)
O4	0.82742 (17)	0.20890 (11)	0.51711 (18)	0.0295 (4)
N1	0.29668 (17)	0.24567 (11)	1.00495 (18)	0.0165 (4)
N2	0.35684 (18)	0.31993 (13)	0.9518 (2)	0.0169 (4)
H1N2	0.328 (2)	0.3673 (18)	0.967 (3)	0.018 (6)*
N3	0.47704 (19)	0.47362 (12)	0.8097 (2)	0.0219 (4)
N4	0.78273 (18)	0.28269 (13)	0.53639 (19)	0.0212 (4)
C1	0.4601 (2)	0.31302 (13)	0.8510 (2)	0.0150 (4)
C2	0.5214 (2)	0.38567 (13)	0.7812 (2)	0.0165 (4)
C3	0.6272 (2)	0.37572 (14)	0.6779 (2)	0.0185 (5)
H3A	0.6662	0.4239	0.6322	0.022*
C4	0.6724 (2)	0.29369 (14)	0.6451 (2)	0.0170 (4)
C5	0.6148 (2)	0.22010 (14)	0.7110 (2)	0.0169 (4)
H5A	0.6469	0.1649	0.6866	0.020*
C6	0.5112 (2)	0.23004 (13)	0.8115 (2)	0.0158 (4)
H6A	0.4731	0.1810	0.8553	0.019*
C7	0.2011 (2)	0.25572 (14)	1.1041 (2)	0.0166 (4)
C8	0.1380 (2)	0.17563 (14)	1.1560 (2)	0.0173 (4)
C9	0.0380 (2)	0.16528 (15)	1.2632 (2)	0.0202 (5)
H9A	−0.0017	0.2113	1.3144	0.024*
C10	0.0020 (2)	0.07644 (14)	1.2874 (2)	0.0188 (5)
H10A	−0.0628	0.0581	1.3565	0.023*
C11	0.0736 (2)	0.02170 (16)	1.1973 (2)	0.0237 (5)
H11A	0.0630	−0.0384	1.1977	0.028*
C12	0.1551 (2)	0.34159 (14)	1.1648 (2)	0.0211 (5)
H12A	0.2364	0.3740	1.1986	0.032*
H12B	0.0941	0.3321	1.2468	0.032*
H12C	0.1054	0.3736	1.0880	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0239 (3)	0.0203 (3)	0.0198 (3)	−0.0021 (2)	0.0103 (2)	−0.0022 (2)
O1	0.0255 (8)	0.0191 (8)	0.0262 (8)	0.0024 (6)	0.0095 (7)	−0.0037 (6)
O2	0.0487 (11)	0.0151 (9)	0.0478 (11)	−0.0032 (8)	0.0247 (9)	0.0050 (8)
O3	0.0254 (8)	0.0333 (10)	0.0206 (8)	−0.0092 (7)	0.0095 (6)	0.0043 (7)
O4	0.0300 (9)	0.0300 (10)	0.0297 (9)	0.0039 (7)	0.0190 (7)	−0.0033 (7)
N1	0.0174 (8)	0.0171 (9)	0.0152 (8)	−0.0018 (7)	0.0052 (7)	−0.0004 (7)
N2	0.0190 (9)	0.0125 (10)	0.0194 (9)	0.0006 (8)	0.0072 (7)	−0.0015 (7)
N3	0.0272 (10)	0.0163 (10)	0.0225 (9)	−0.0019 (8)	0.0058 (8)	0.0020 (8)
N4	0.0188 (9)	0.0277 (11)	0.0174 (9)	−0.0020 (8)	0.0063 (7)	−0.0013 (8)
C1	0.0150 (9)	0.0188 (11)	0.0113 (9)	−0.0003 (8)	0.0024 (7)	−0.0001 (8)
C2	0.0181 (10)	0.0142 (10)	0.0173 (10)	−0.0011 (8)	0.0035 (8)	−0.0003 (8)
C3	0.0205 (10)	0.0188 (11)	0.0162 (10)	−0.0045 (9)	0.0026 (8)	0.0037 (8)
C4	0.0160 (10)	0.0234 (12)	0.0120 (9)	−0.0024 (9)	0.0075 (8)	0.0008 (8)
C5	0.0182 (10)	0.0173 (11)	0.0152 (10)	0.0023 (8)	0.0029 (8)	−0.0026 (8)
C6	0.0182 (10)	0.0147 (10)	0.0148 (9)	−0.0012 (8)	0.0048 (8)	0.0009 (8)
C7	0.0172 (10)	0.0199 (11)	0.0127 (9)	0.0008 (8)	0.0020 (8)	−0.0018 (8)
C8	0.0160 (10)	0.0216 (12)	0.0143 (10)	0.0004 (8)	0.0031 (8)	−0.0027 (8)
C9	0.0187 (10)	0.0261 (12)	0.0163 (10)	0.0004 (9)	0.0065 (8)	−0.0025 (9)
C10	0.0168 (10)	0.0256 (12)	0.0146 (10)	−0.0032 (9)	0.0094 (8)	0.0001 (9)
C11	0.0251 (11)	0.0236 (12)	0.0229 (11)	−0.0064 (9)	0.0076 (9)	0.0018 (9)
C12	0.0228 (11)	0.0219 (12)	0.0191 (11)	0.0001 (9)	0.0093 (9)	−0.0025 (9)

Geometric parameters (Å, º) top

S1—C11	1.714 (2)	C3—H3A	0.9300
S1—C8	1.731 (2)	C4—C5	1.396 (3)
O1—N3	1.245 (2)	C5—C6	1.362 (3)
O2—N3	1.226 (2)	C5—H5A	0.9300
O3—N4	1.228 (2)	C6—H6A	0.9300
O4—N4	1.226 (2)	C7—C8	1.453 (3)
N1—C7	1.298 (3)	C7—C12	1.499 (3)
N1—N2	1.370 (3)	C8—C9	1.380 (3)
N2—C1	1.357 (3)	C9—C10	1.428 (3)
N2—H1N2	0.79 (3)	C9—H9A	0.9300
N3—C2	1.443 (3)	C10—C11	1.363 (3)
N4—C4	1.462 (3)	C10—H10A	0.9300
C1—C2	1.415 (3)	C11—H11A	0.9300
C1—C6	1.415 (3)	C12—H12A	0.9600
C2—C3	1.394 (3)	C12—H12B	0.9600
C3—C4	1.368 (3)	C12—H12C	0.9600

C11—S1—C8	91.98 (11)	C4—C5—H5A	120.4
C7—N1—N2	116.47 (18)	C5—C6—C1	121.80 (19)
C1—N2—N1	118.89 (18)	C5—C6—H6A	119.1
C1—N2—H1N2	116.4 (18)	C1—C6—H6A	119.1
N1—N2—H1N2	124.2 (18)	N1—C7—C8	114.90 (19)
O2—N3—O1	121.94 (18)	N1—C7—C12	124.81 (19)
O2—N3—C2	119.03 (18)	C8—C7—C12	120.30 (18)
O1—N3—C2	119.03 (17)	C9—C8—C7	128.3 (2)
O4—N4—O3	123.94 (18)	C9—C8—S1	110.63 (16)
O4—N4—C4	117.31 (18)	C7—C8—S1	121.11 (15)
O3—N4—C4	118.75 (18)	C8—C9—C10	112.89 (19)
N2—C1—C2	123.19 (19)	C8—C9—H9A	123.6
N2—C1—C6	119.84 (18)	C10—C9—H9A	123.6
C2—C1—C6	116.98 (18)	C11—C10—C9	112.11 (19)
C3—C2—C1	121.38 (19)	C11—C10—H10A	123.9
C3—C2—N3	116.11 (18)	C9—C10—H10A	123.9
C1—C2—N3	122.50 (18)	C10—C11—S1	112.39 (18)
C4—C3—C2	118.73 (19)	C10—C11—H11A	123.8
C4—C3—H3A	120.6	S1—C11—H11A	123.8
C2—C3—H3A	120.6	C7—C12—H12A	109.5
C3—C4—C5	121.90 (19)	C7—C12—H12B	109.5
C3—C4—N4	119.07 (19)	H12A—C12—H12B	109.5
C5—C4—N4	119.03 (19)	C7—C12—H12C	109.5
C6—C5—C4	119.21 (19)	H12A—C12—H12C	109.5
C6—C5—H5A	120.4	H12B—C12—H12C	109.5

C7—N1—N2—C1	178.22 (17)	C3—C4—C5—C6	−0.4 (3)
N1—N2—C1—C2	175.14 (17)	N4—C4—C5—C6	−179.49 (17)
N1—N2—C1—C6	−4.9 (3)	C4—C5—C6—C1	0.0 (3)
N2—C1—C2—C3	−179.90 (18)	N2—C1—C6—C5	−179.89 (18)
C6—C1—C2—C3	0.2 (3)	C2—C1—C6—C5	0.1 (3)
N2—C1—C2—N3	−1.2 (3)	N2—N1—C7—C8	178.99 (16)
C6—C1—C2—N3	178.88 (17)	N2—N1—C7—C12	−1.1 (3)
O2—N3—C2—C3	−1.9 (3)	N1—C7—C8—C9	177.69 (19)
O1—N3—C2—C3	178.29 (17)	C12—C7—C8—C9	−2.2 (3)
O2—N3—C2—C1	179.28 (19)	N1—C7—C8—S1	−2.2 (2)
O1—N3—C2—C1	−0.5 (3)	C12—C7—C8—S1	177.89 (15)
C1—C2—C3—C4	−0.5 (3)	C11—S1—C8—C9	−0.67 (16)
N3—C2—C3—C4	−179.26 (17)	C11—S1—C8—C7	179.21 (17)
C2—C3—C4—C5	0.6 (3)	C7—C8—C9—C10	−178.97 (19)
C2—C3—C4—N4	179.69 (17)	S1—C8—C9—C10	0.9 (2)
O4—N4—C4—C3	175.19 (18)	C8—C9—C10—C11	−0.7 (3)
O3—N4—C4—C3	−5.1 (3)	C9—C10—C11—S1	0.2 (2)
O4—N4—C4—C5	−5.7 (3)	C8—S1—C11—C10	0.27 (17)
O3—N4—C4—C5	174.08 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1	0.79 (3)	2.00 (3)	2.618 (3)	134 (2)
C6—H6A···O2ⁱ	0.93	2.45	3.099 (3)	127
C9—H9A···O4ⁱⁱ	0.93	2.47	3.147 (2)	129
C11—H11A···O3ⁱ	0.93	2.57	3.240 (3)	129

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x−1, y, z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀N₄O₄S
M_r	306.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.4868 (5), 15.3912 (8), 8.9756 (4)
β (°)	91.672 (2)
V (Å³)	1310.00 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.60 × 0.19 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.854, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	10366, 2414, 2176
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.109, 1.08
No. of reflections	2414
No. of parameters	195
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.44

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
N2—H1N2···O1	0.79 (3)	2.00 (3)	2.618 (3)	134 (2)
C6—H6A···O2ⁱ	0.93	2.45	3.099 (3)	127
C9—H9A···O4ⁱⁱ	0.93	2.47	3.147 (2)	129
C11—H11A···O3ⁱ	0.93	2.57	3.240 (3)	129

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x−1, y, z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th, Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

PJ thanks the Graduate School, Prince of Songkla University, for partial financial support. The authors thank the Prince of Songkla University for financial support through the Crystal Materials Research Unit (CMRU), and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

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