1-(2,3-Dimeth­oxy­benzyl­idene)-2-(2,4-dinitro­phen­yl)hydrazine

Xin, X.; Li, M.; Chen, Z.; Zhu, R.

doi:10.1107/S1600536811013894

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1169

doi:10.1107/S1600536811013894

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1-(2,3-Dimethoxybenzylidene)-2-(2,4-dinitrophenyl)hydrazine

Xianrong Xin,^a Min Li,^a Zhimin Chen ^a and Ruitao Zhu ^b ^*

^aDepartment of Chemistry and Chemical Engineering, Taiyuan Institute of Technology, Taiyuan 030008, People's Republic of China, and ^bDepartment of Chemistry, Taiyuan Normal University, Taiyuan 030031, People's Republic of China
^*Correspondence e-mail: ruitaozhu@126.com

(Received 29 March 2011; accepted 13 April 2011; online 16 April 2011)

In the title compound, C₁₅H₁₄N₄O₆, the dihedral angle between the aromatic rings is 3.7 (4)°. The nitro groups make dihedral angles of 6.0 (4) and 5.2 (4)° with the parent ring and are oriented at 6.0 (6)° with respect to each other. The methoxy groups are inclined at 54.0 (2) and 2.5 (3)° with respect to the benzene ring to which they are attached. In the crystal, molecules are linked by weak C—H⋯O interactions. The molecular conformation is consolidated by an intramolecular N—H⋯O hydrogen bond.

Related literature

For general background to the properties of Schiff base compounds, see: Mufakkar et al. (2010 ); Tahir et al. (2010 ). For related structures, see: Salhin et al. (2007 ); Tameem et al. (2008 ); Shao et al. (2008 ).

Experimental

Crystal data

C₁₅H₁₄N₄O₆
M_r = 346.30
Triclinic, $[P \overline 1]$
a = 7.8409 (8) Å
b = 7.9200 (9) Å
c = 13.8961 (14) Å
α = 85.038 (2)°
β = 82.773 (1)°
γ = 65.894 (1)°
V = 780.85 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 298 K
0.43 × 0.38 × 0.37 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.952, T_max = 0.958
4130 measured reflections
2725 independent reflections
1414 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.178
S = 1.06
2725 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.28 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
N1—H1⋯O1	0.86	1.99	2.625 (4)	130
C14—H14A⋯O4ⁱ	0.96	2.48	3.431 (4)	170
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: SMART (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: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013894/pv2405sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013894/pv2405Isup2.hkl

checkCIF report

Comment top

In view of the importance of hydrazone derivatives in chemical and biological applications (Shao et al., 2008), a series of hydrazone derivatives has been prepared, and several X-ray structures have been reported (Salhin et al., 2007; Aameem et al., 2008). Here, we report the crystal structure of the title compound.

The bond distances and bond angles in the title compound (Fig. 1) are in agreement with the corresponding bond distances and angles reported in the crystale structures of closely related compounds, (Salhin et al., 2007; Tameem et al., 2008). In the crystal structure (Fig. 2), the molecules are linked by C—H···O weak interactions (Table 1). The molecular conformation is consolidated by an intramolecular N—H···O hydrogen bonding interaction (Table 1).

Related literature top

For general background to the properties of Schiff base compounds, see: Mufakkar et al. (2010); Tahir et al. (2010). For related structures, see: Salhin et al. (2007); Tameem et al. (2008); Shao et al. (2008).

Experimental top

Equimolar quantities of 2,4-dinitrophenylhydrazine (0.99 g, 5.0 mmol) and 2,3-dimethoxybenzaldehyde (0.83 g, 5.0 mmol) were refluxed in ethanol (20 ml) for 30 min and rotary evaporated. The crystals of the title compound were growm by recrystallization from an ethanol solution.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of the title compound; displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of (I) with hydrogen bonds drawn as dashed lines.

1-(2,3-Dimethoxybenzylidene)-2-(2,4-dinitrophenyl)hydrazine top

Crystal data top

C₁₅H₁₄N₄O₆	Z = 2
M_r = 346.30	F(000) = 360
Triclinic, P1	D_x = 1.473 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8409 (8) Å	Cell parameters from 855 reflections
b = 7.9200 (9) Å	θ = 2.8–22.8°
c = 13.8961 (14) Å	µ = 0.12 mm⁻¹
α = 85.038 (2)°	T = 298 K
β = 82.773 (1)°	Block, orange
γ = 65.894 (1)°	0.43 × 0.38 × 0.37 mm
V = 780.85 (14) Å³

Data collection top

Bruker SMART CCD diffractometer	2725 independent reflections
Radiation source: fine-focus sealed tube	1414 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→9
T_min = 0.952, T_max = 0.958	k = −9→9
4130 measured reflections	l = −16→8

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.063	H-atom parameters constrained
wR(F²) = 0.178	w = 1/[σ²(F_o²) + (0.0737P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2725 reflections	Δρ_max = 0.28 e Å⁻³
229 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.028 (5)

Crystal data top

C₁₅H₁₄N₄O₆	γ = 65.894 (1)°
M_r = 346.30	V = 780.85 (14) Å³
Triclinic, P1	Z = 2
a = 7.8409 (8) Å	Mo Kα radiation
b = 7.9200 (9) Å	µ = 0.12 mm⁻¹
c = 13.8961 (14) Å	T = 298 K
α = 85.038 (2)°	0.43 × 0.38 × 0.37 mm
β = 82.773 (1)°

Data collection top

Bruker SMART CCD diffractometer	2725 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1414 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.958	R_int = 0.032
4130 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 1.06	Δρ_max = 0.28 e Å⁻³
2725 reflections	Δρ_min = −0.25 e Å⁻³
229 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
N1	0.6288 (3)	0.1887 (3)	0.55122 (17)	0.0672 (7)
H1	0.7290	0.1995	0.5243	0.081*
N2	0.4685 (3)	0.2598 (3)	0.50406 (17)	0.0627 (6)
N3	0.9691 (3)	0.0341 (4)	0.6504 (3)	0.0789 (8)
N4	0.6248 (5)	−0.1660 (4)	0.9164 (2)	0.0889 (9)
O1	0.9777 (3)	0.1238 (4)	0.57412 (19)	0.0936 (8)
O2	1.1061 (3)	−0.0474 (4)	0.6963 (2)	0.1191 (10)
O3	0.7741 (4)	−0.2406 (4)	0.9539 (2)	0.1259 (11)
O4	0.4763 (4)	−0.1674 (4)	0.95499 (18)	0.1107 (9)
O5	0.5156 (3)	0.5336 (3)	0.25258 (14)	0.0734 (6)
O6	0.2347 (3)	0.6845 (3)	0.13346 (16)	0.0810 (7)
C1	0.6302 (3)	0.1025 (3)	0.6391 (2)	0.0549 (7)
C2	0.7926 (3)	0.0256 (4)	0.6903 (2)	0.0626 (8)
C3	0.7883 (4)	−0.0608 (4)	0.7802 (2)	0.0681 (8)
H3	0.8956	−0.1094	0.8130	0.082*
C4	0.6287 (4)	−0.0754 (4)	0.8214 (2)	0.0652 (8)
C5	0.4661 (4)	−0.0033 (4)	0.7723 (2)	0.0651 (8)
H5	0.3567	−0.0136	0.8008	0.078*
C6	0.4688 (4)	0.0809 (4)	0.6841 (2)	0.0609 (7)
H6	0.3609	0.1260	0.6518	0.073*
C7	0.4850 (4)	0.3361 (4)	0.4206 (2)	0.0627 (7)
H7	0.6000	0.3394	0.3968	0.075*
C8	0.3275 (4)	0.4181 (4)	0.3620 (2)	0.0588 (7)
C9	0.3505 (4)	0.5101 (4)	0.2741 (2)	0.0602 (7)
C10	0.2012 (4)	0.5909 (4)	0.2156 (2)	0.0641 (8)
C11	0.0346 (4)	0.5735 (4)	0.2461 (2)	0.0744 (9)
H11	−0.0643	0.6240	0.2074	0.089*
C12	0.0117 (4)	0.4825 (4)	0.3330 (3)	0.0756 (9)
H12	−0.1026	0.4740	0.3525	0.091*
C13	0.1564 (4)	0.4046 (4)	0.3907 (2)	0.0684 (8)
H13	0.1404	0.3428	0.4488	0.082*
C14	0.6191 (4)	0.4797 (5)	0.1608 (2)	0.0847 (10)
H14A	0.5771	0.3991	0.1323	0.127*
H14B	0.7503	0.4159	0.1691	0.127*
H14C	0.5998	0.5877	0.1190	0.127*
C15	0.0951 (5)	0.7525 (5)	0.0675 (3)	0.1016 (12)
H15A	0.0718	0.6516	0.0472	0.152*
H15B	0.1378	0.8107	0.0118	0.152*
H15C	−0.0187	0.8412	0.0987	0.152*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0509 (13)	0.0903 (17)	0.0649 (17)	−0.0324 (12)	−0.0047 (11)	−0.0079 (13)
N2	0.0547 (14)	0.0696 (15)	0.0639 (16)	−0.0245 (12)	−0.0081 (11)	−0.0030 (12)
N3	0.0472 (15)	0.0818 (19)	0.110 (2)	−0.0237 (14)	−0.0100 (15)	−0.0246 (16)
N4	0.117 (3)	0.088 (2)	0.081 (2)	−0.0550 (19)	−0.0386 (19)	0.0088 (16)
O1	0.0661 (14)	0.133 (2)	0.0922 (18)	−0.0513 (14)	0.0068 (12)	−0.0250 (15)
O2	0.0526 (13)	0.124 (2)	0.180 (3)	−0.0300 (13)	−0.0379 (16)	0.0068 (18)
O3	0.136 (2)	0.138 (2)	0.114 (2)	−0.0557 (18)	−0.0725 (19)	0.0353 (17)
O4	0.142 (2)	0.140 (2)	0.0873 (19)	−0.095 (2)	−0.0317 (16)	0.0251 (15)
O5	0.0724 (13)	0.0967 (15)	0.0642 (13)	−0.0473 (12)	−0.0049 (10)	−0.0064 (10)
O6	0.0827 (14)	0.0920 (15)	0.0730 (15)	−0.0389 (12)	−0.0219 (11)	0.0126 (12)
C1	0.0492 (15)	0.0540 (15)	0.0625 (19)	−0.0194 (13)	−0.0076 (12)	−0.0111 (13)
C2	0.0461 (16)	0.0640 (18)	0.080 (2)	−0.0201 (13)	−0.0103 (14)	−0.0183 (16)
C3	0.0621 (19)	0.0584 (17)	0.087 (2)	−0.0196 (15)	−0.0281 (16)	−0.0119 (16)
C4	0.077 (2)	0.0615 (17)	0.066 (2)	−0.0324 (15)	−0.0250 (15)	−0.0003 (14)
C5	0.0628 (18)	0.0648 (18)	0.076 (2)	−0.0329 (15)	−0.0142 (15)	0.0020 (15)
C6	0.0515 (16)	0.0651 (17)	0.070 (2)	−0.0256 (13)	−0.0144 (13)	−0.0007 (15)
C7	0.0573 (17)	0.0741 (19)	0.0600 (19)	−0.0302 (15)	−0.0019 (13)	−0.0060 (15)
C8	0.0543 (16)	0.0630 (17)	0.0602 (18)	−0.0240 (14)	−0.0005 (13)	−0.0129 (13)
C9	0.0572 (17)	0.0653 (17)	0.0628 (19)	−0.0287 (14)	−0.0009 (13)	−0.0125 (14)
C10	0.0627 (18)	0.0639 (18)	0.067 (2)	−0.0250 (15)	−0.0085 (14)	−0.0074 (15)
C11	0.0620 (19)	0.075 (2)	0.089 (2)	−0.0260 (16)	−0.0185 (16)	−0.0074 (17)
C12	0.0578 (18)	0.078 (2)	0.095 (3)	−0.0327 (16)	0.0006 (17)	−0.0115 (18)
C13	0.0627 (18)	0.0689 (19)	0.076 (2)	−0.0293 (15)	−0.0014 (15)	−0.0098 (15)
C14	0.080 (2)	0.113 (3)	0.072 (2)	−0.051 (2)	−0.0011 (16)	−0.0033 (18)
C15	0.095 (3)	0.120 (3)	0.084 (3)	−0.035 (2)	−0.032 (2)	0.019 (2)

Geometric parameters (Å, º) top

N1—C1	1.345 (3)	C5—C6	1.347 (4)
N1—N2	1.375 (3)	C5—H5	0.9300
N1—H1	0.8600	C6—H6	0.9300
N2—C7	1.278 (3)	C7—C8	1.455 (4)
N3—O2	1.230 (3)	C7—H7	0.9300
N3—O1	1.234 (3)	C8—C13	1.395 (4)
N3—C2	1.451 (4)	C8—C9	1.397 (4)
N4—O4	1.223 (3)	C9—C10	1.408 (4)
N4—O3	1.236 (3)	C10—C11	1.379 (4)
N4—C4	1.450 (4)	C11—C12	1.382 (4)
O5—C9	1.375 (3)	C11—H11	0.9300
O5—C14	1.420 (3)	C12—C13	1.372 (4)
O6—C10	1.363 (3)	C12—H12	0.9300
O6—C15	1.420 (3)	C13—H13	0.9300
C1—C6	1.407 (4)	C14—H14A	0.9600
C1—C2	1.421 (4)	C14—H14B	0.9600
C2—C3	1.375 (4)	C14—H14C	0.9600
C3—C4	1.355 (4)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.404 (4)	C15—H15C	0.9600

C1—N1—N2	120.6 (2)	C8—C7—H7	119.4
C1—N1—H1	119.7	C13—C8—C9	119.6 (3)
N2—N1—H1	119.7	C13—C8—C7	121.7 (3)
C7—N2—N1	114.9 (2)	C9—C8—C7	118.7 (2)
O2—N3—O1	122.2 (3)	O5—C9—C8	117.6 (2)
O2—N3—C2	117.5 (3)	O5—C9—C10	121.8 (3)
O1—N3—C2	120.3 (3)	C8—C9—C10	120.2 (3)
O4—N4—O3	123.2 (3)	O6—C10—C11	125.7 (3)
O4—N4—C4	119.1 (3)	O6—C10—C9	115.8 (3)
O3—N4—C4	117.7 (3)	C11—C10—C9	118.4 (3)
C9—O5—C14	118.8 (2)	C10—C11—C12	121.4 (3)
C10—O6—C15	117.7 (2)	C10—C11—H11	119.3
N1—C1—C6	120.8 (2)	C12—C11—H11	119.3
N1—C1—C2	122.6 (3)	C13—C12—C11	120.4 (3)
C6—C1—C2	116.5 (3)	C13—C12—H12	119.8
C3—C2—C1	121.0 (3)	C11—C12—H12	119.8
C3—C2—N3	117.3 (3)	C12—C13—C8	120.0 (3)
C1—C2—N3	121.8 (3)	C12—C13—H13	120.0
C4—C3—C2	120.4 (3)	C8—C13—H13	120.0
C4—C3—H3	119.8	O5—C14—H14A	109.5
C2—C3—H3	119.8	O5—C14—H14B	109.5
C3—C4—C5	120.2 (3)	H14A—C14—H14B	109.5
C3—C4—N4	120.1 (3)	O5—C14—H14C	109.5
C5—C4—N4	119.6 (3)	H14A—C14—H14C	109.5
C6—C5—C4	119.9 (3)	H14B—C14—H14C	109.5
C6—C5—H5	120.0	O6—C15—H15A	109.5
C4—C5—H5	120.0	O6—C15—H15B	109.5
C5—C6—C1	121.9 (2)	H15A—C15—H15B	109.5
C5—C6—H6	119.0	O6—C15—H15C	109.5
C1—C6—H6	119.0	H15A—C15—H15C	109.5
N2—C7—C8	121.3 (3)	H15B—C15—H15C	109.5
N2—C7—H7	119.4

C1—N1—N2—C7	−179.1 (2)	C2—C1—C6—C5	2.0 (4)
N2—N1—C1—C6	0.9 (4)	N1—N2—C7—C8	−179.8 (2)
N2—N1—C1—C2	179.5 (2)	N2—C7—C8—C13	−5.0 (4)
N1—C1—C2—C3	179.7 (2)	N2—C7—C8—C9	175.9 (2)
C6—C1—C2—C3	−1.7 (4)	C14—O5—C9—C8	129.0 (3)
N1—C1—C2—N3	−0.4 (4)	C14—O5—C9—C10	−57.3 (4)
C6—C1—C2—N3	178.2 (2)	C13—C8—C9—O5	174.7 (2)
O2—N3—C2—C3	4.9 (4)	C7—C8—C9—O5	−6.3 (4)
O1—N3—C2—C3	−173.6 (3)	C13—C8—C9—C10	0.9 (4)
O2—N3—C2—C1	−174.9 (3)	C7—C8—C9—C10	180.0 (2)
O1—N3—C2—C1	6.6 (4)	C15—O6—C10—C11	−7.7 (4)
C1—C2—C3—C4	0.6 (4)	C15—O6—C10—C9	173.9 (3)
N3—C2—C3—C4	−179.3 (2)	O5—C9—C10—O6	3.7 (4)
C2—C3—C4—C5	0.3 (4)	C8—C9—C10—O6	177.2 (2)
C2—C3—C4—N4	−179.8 (2)	O5—C9—C10—C11	−174.8 (2)
O4—N4—C4—C3	175.4 (3)	C8—C9—C10—C11	−1.4 (4)
O3—N4—C4—C3	−5.5 (4)	O6—C10—C11—C12	−177.0 (3)
O4—N4—C4—C5	−4.7 (4)	C9—C10—C11—C12	1.3 (4)
O3—N4—C4—C5	174.4 (3)	C10—C11—C12—C13	−0.9 (5)
C3—C4—C5—C6	0.0 (4)	C11—C12—C13—C8	0.4 (5)
N4—C4—C5—C6	−179.9 (2)	C9—C8—C13—C12	−0.5 (4)
C4—C5—C6—C1	−1.2 (4)	C7—C8—C13—C12	−179.5 (3)
N1—C1—C6—C5	−179.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.99	2.625 (4)	130
N1—H1···N3	0.86	2.60	2.913 (4)	103
C3—H3···O2	0.93	2.33	2.654 (4)	100
C6—H6···N2	0.93	2.44	2.766 (4)	100
C7—H7···O5	0.93	2.41	2.737 (4)	101
C14—H14A···O4ⁱ	0.96	2.48	3.431 (4)	170

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₄O₆
M_r	346.30
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.8409 (8), 7.9200 (9), 13.8961 (14)
α, β, γ (°)	85.038 (2), 82.773 (1), 65.894 (1)
V (Å³)	780.85 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.43 × 0.38 × 0.37

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.952, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	4130, 2725, 1414
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.178, 1.06
No. of reflections	2725
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.25

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.99	2.625 (4)	130
C14—H14A···O4ⁱ	0.96	2.48	3.431 (4)	170

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

The authors thank Professor Daqi Wang, Liaocheng University, for use of the X-ray diffraction facility.

References

Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Mufakkar, M., Tahir, M. N., Tariq, M. I., Ahmad, S. & Sarfraz, M. (2010). Acta Cryst. E66, o1887. Web of Science CSD CrossRef IUCr Journals Google Scholar
Salhin, A., Tameem, A. A., Saad, B., Ng, S.-L. & Fun, H.-K. (2007). Acta Cryst. E63, o2880. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shao, J., Lin, I., Yu, M., Cai, Z. & Lin, I. (2008). Talanta, 75, 551–555. Web of Science CrossRef PubMed 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
Tahir, M. N., Tariq, M. I., Ahmad, S., Sarfraz, M. & Ather, A. Q. (2010). Acta Cryst. E66, o1817. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tameem, A., Saad, B., Salhin, A. M., Jebas, S. R. & Fun, H.-K. (2008). Acta Cryst. E64, o679–o680. Web of Science CrossRef IUCr Journals Google Scholar