Ethyl 5-methyl-1-(4-nitro­phen­yl)-1H-1,2,3-triazole-4-carboxyl­ate

Fun, H.-K.; Quah, C.K.; Nithinchandra; Kalluraya, B.

doi:10.1107/S1600536811033940

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2416

doi:10.1107/S1600536811033940

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Ethyl 5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxylate

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Nithinchandra ^b and Balakrishna Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 18 August 2011; accepted 19 August 2011; online 27 August 2011)

In the title compound, C₁₂H₁₂N₄O₄, the 1,2,3-triazole ring and the nitro group form dihedral angles of 37.93 (5) and 8.97 (12)°, respectively, with the phenyl ring. The molecular structure is stabilized by an intramolecular C—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, molecules are linked by C—H⋯N hydrogen bonds into layers lying parallel to (100). The crystal structure is further consolidated by π–π [centroid–centroid distance = 3.6059 (6) Å] interactions.

Related literature

For general background to and the biological activity of 1,2,3-triazole derivatives, see: Sherement et al. (2004 ); Danoun et al. (1998 ); Manfredini et al. (2000 ); Biagi et al. (2004 ). For standard bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ). For related structures, see: Fun, Quah, Chandrakantha et al. (2011 ); Fun, Quah, Nithinchandra et al. (2011 ).

Experimental

Crystal data

C₁₂H₁₂N₄O₄
M_r = 276.26
Monoclinic, P 2₁ /c
a = 13.5309 (3) Å
b = 7.3014 (2) Å
c = 12.6058 (3) Å
β = 99.574 (1)°
V = 1228.04 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 100 K
0.50 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.944, T_max = 0.982
16800 measured reflections
4469 independent reflections
3699 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.114
S = 1.03
4469 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯N3ⁱ	0.95	2.59	3.5243 (12)	168
C5—H5A⋯N2ⁱⁱ	0.95	2.60	3.2347 (12)	125
C5—H5A⋯N3ⁱⁱ	0.95	2.54	3.4127 (12)	154
C10—H10B⋯O4	0.98	2.48	3.0936 (12)	120
Symmetry codes: (i) -x+1, -y, -z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536811033940/hb6375sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033940/hb6375Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811033940/hb6375Isup3.cml

checkCIF report

Comment top

1,2,3-Triazole and its derivatives had attracted considerable attention for the past few decades due to their chemotherapeutical value. Many 1,2,3-triazoles are found to be potent antimicrobial (Sherement et al., 2004) and antiviral agents. Some of them have exhibited antiproliferative and anticancer activities (Danoun et al., 1998). Some 1,2,3-triazoles are used as DNA cleaving agents (Manfredini et al., 2000) and potassium channel activators (Biagi et al., 2004). Prompted by the chemotherapeutic importance of 1,2,3-triazoles and its derivatives, we synthesized the title compound.

In the title molecule, Fig. 1, the 1,2,3-triazole ring (N1-N3/C7/C8, maximum deviation of 0.003 (1) Å at atoms N2 and N3) and the nitro group (O2/O3/N4) form dihedral angles of 37.93 (5) and 8.97 (12)°, respectively, with the phenyl ring (C1-C6). Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun, Quah, Chandrakantha et al., 2011; Fun, Quah, Nithinchandra et al., 2011). The molecular structure is stabilized by an intramolecular C41-H10B···O4 hydrogen bond (Table 1), which generates an S(6) ring motif (Fig. 1, Bernstein et al., 1995).

In the crystal structure, Fig. 2, molecules are linked via intermolecular C1–H1A···N3, C5–H5A···N2 and C5–H5A···N3 hydrogen bonds (Table 1) into two-dimensional planes parallel to (100). π-π stacking interactions between the centroids of C1-C6 phenyl ring (Cg1) and N1-N3/C7/C8 triazole ring (Cg2), with Cg1···Cg2ⁱⁱⁱ distance of 3.6059 (6) Å [symmetry code: (iii) 1-X,-1/2+Y,1/2-Z] are observed.

Related literature top

For general background to and the biological activity of 1,2,3-triazole derivatives, see: Sherement et al. (2004); Danoun et al. (1998); Manfredini et al. (2000); Biagi et al. (2004). For standard bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). For related structures, see: Fun, Quah, Chandrakantha et al. (2011); Fun, Quah, Nithinchandra et al. (2011).

Experimental top

1-Azido-4-nitrobenzene (15 g) was treated with ethyl acetoacetate (8.3 g) in methanol (75 ml) and the mixture was cooled to 273 K. Sodium methoxide (3.5 g) was added under inert atmosphere to the above mixture and stirred at ambient temperature for 8 h. Progress of the reaction was monitored by TLC (ethyl acetate/n-hexane, 2:3, v/v). After completion of the reaction, the mixture was poured on to ice cold water. The precipitated solid was filtered, washed with water and recrystallized from methanol. Colourless plates of (I) were obtained from DMF by slow evaporation.

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 for non-H atoms. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

Ethyl 5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carboxylate top

Crystal data top

C₁₂H₁₂N₄O₄	F(000) = 576
M_r = 276.26	D_x = 1.494 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8459 reflections
a = 13.5309 (3) Å	θ = 3.1–32.6°
b = 7.3014 (2) Å	µ = 0.12 mm⁻¹
c = 12.6058 (3) Å	T = 100 K
β = 99.574 (1)°	Plate, colourless
V = 1228.04 (5) Å³	0.50 × 0.16 × 0.16 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4469 independent reflections
Radiation source: fine-focus sealed tube	3699 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 32.6°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→18
T_min = 0.944, T_max = 0.982	k = −11→8
16800 measured reflections	l = −19→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0579P)² + 0.3698P] where P = (F_o² + 2F_c²)/3
4469 reflections	(Δ/σ)_max = 0.001
183 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₂H₁₂N₄O₄	V = 1228.04 (5) Å³
M_r = 276.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.5309 (3) Å	µ = 0.12 mm⁻¹
b = 7.3014 (2) Å	T = 100 K
c = 12.6058 (3) Å	0.50 × 0.16 × 0.16 mm
β = 99.574 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4469 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3699 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.982	R_int = 0.021
16800 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.03	Δρ_max = 0.41 e Å⁻³
4469 reflections	Δρ_min = −0.30 e Å⁻³
183 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 100.0 (1) K.

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	0.17538 (5)	0.16665 (10)	−0.05384 (5)	0.01804 (15)
O2	0.81492 (6)	0.19872 (12)	0.56912 (6)	0.02603 (18)
O3	0.88912 (6)	0.04601 (13)	0.45702 (7)	0.02874 (19)
O4	0.14766 (5)	0.02184 (11)	0.09686 (6)	0.02182 (16)
N1	0.45814 (6)	0.12739 (11)	0.18124 (6)	0.01308 (15)
N2	0.46803 (6)	0.17529 (12)	0.07841 (6)	0.01609 (16)
N3	0.37872 (6)	0.17308 (12)	0.02083 (6)	0.01568 (16)
N4	0.81564 (6)	0.12105 (13)	0.48264 (7)	0.01954 (17)
C1	0.63468 (7)	0.05446 (13)	0.22772 (7)	0.01570 (17)
H1A	0.6336	0.0113	0.1564	0.019*
C2	0.72344 (7)	0.05470 (13)	0.30098 (7)	0.01654 (17)
H2A	0.7841	0.0126	0.2807	0.020*
C3	0.72162 (7)	0.11789 (13)	0.40463 (7)	0.01516 (17)
C4	0.63467 (7)	0.17883 (13)	0.43757 (7)	0.01519 (17)
H4A	0.6358	0.2197	0.5093	0.018*
C5	0.54574 (7)	0.17947 (13)	0.36424 (7)	0.01414 (16)
H5A	0.4852	0.2209	0.3850	0.017*
C6	0.54695 (6)	0.11829 (13)	0.25977 (7)	0.01296 (16)
C7	0.36061 (6)	0.09299 (12)	0.18864 (7)	0.01266 (16)
C8	0.31097 (7)	0.12254 (13)	0.08482 (7)	0.01365 (16)
C9	0.20306 (7)	0.09756 (13)	0.04465 (7)	0.01549 (17)
C10	0.32346 (7)	0.03491 (14)	0.28808 (7)	0.01660 (18)
H10A	0.3749	−0.0389	0.3327	0.025*
H10B	0.2624	−0.0381	0.2686	0.025*
H10C	0.3087	0.1434	0.3284	0.025*
C11	0.06813 (7)	0.14784 (16)	−0.09678 (8)	0.0212 (2)
H11A	0.0276	0.1941	−0.0440	0.025*
H11B	0.0510	0.0175	−0.1116	0.025*
C12	0.04675 (8)	0.25753 (17)	−0.19890 (8)	0.0252 (2)
H12A	−0.0243	0.2459	−0.2301	0.038*
H12B	0.0879	0.2116	−0.2502	0.038*
H12C	0.0627	0.3866	−0.1830	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0132 (3)	0.0239 (4)	0.0165 (3)	−0.0003 (3)	0.0008 (2)	0.0035 (3)
O2	0.0228 (4)	0.0363 (5)	0.0175 (3)	−0.0044 (3)	−0.0011 (3)	0.0009 (3)
O3	0.0157 (3)	0.0370 (5)	0.0330 (4)	0.0053 (3)	0.0024 (3)	0.0051 (4)
O4	0.0167 (3)	0.0304 (4)	0.0189 (3)	−0.0049 (3)	0.0043 (2)	0.0031 (3)
N1	0.0132 (3)	0.0159 (4)	0.0106 (3)	−0.0003 (3)	0.0035 (2)	0.0001 (3)
N2	0.0153 (3)	0.0219 (4)	0.0116 (3)	−0.0003 (3)	0.0039 (3)	0.0019 (3)
N3	0.0146 (3)	0.0198 (4)	0.0130 (3)	−0.0003 (3)	0.0036 (3)	0.0011 (3)
N4	0.0155 (4)	0.0227 (4)	0.0197 (4)	−0.0016 (3)	0.0009 (3)	0.0060 (3)
C1	0.0166 (4)	0.0165 (4)	0.0150 (4)	0.0002 (3)	0.0056 (3)	−0.0009 (3)
C2	0.0143 (4)	0.0169 (4)	0.0194 (4)	0.0013 (3)	0.0057 (3)	0.0007 (3)
C3	0.0136 (4)	0.0156 (4)	0.0159 (4)	−0.0009 (3)	0.0013 (3)	0.0030 (3)
C4	0.0159 (4)	0.0164 (4)	0.0133 (3)	−0.0003 (3)	0.0027 (3)	0.0012 (3)
C5	0.0141 (4)	0.0158 (4)	0.0130 (3)	0.0006 (3)	0.0037 (3)	0.0001 (3)
C6	0.0130 (4)	0.0132 (4)	0.0128 (3)	−0.0004 (3)	0.0028 (3)	0.0008 (3)
C7	0.0136 (4)	0.0121 (4)	0.0129 (3)	−0.0009 (3)	0.0041 (3)	−0.0005 (3)
C8	0.0141 (4)	0.0152 (4)	0.0124 (3)	−0.0004 (3)	0.0042 (3)	−0.0003 (3)
C9	0.0149 (4)	0.0175 (4)	0.0142 (4)	0.0006 (3)	0.0027 (3)	−0.0014 (3)
C10	0.0176 (4)	0.0198 (4)	0.0134 (4)	−0.0026 (3)	0.0057 (3)	0.0010 (3)
C11	0.0130 (4)	0.0282 (5)	0.0213 (4)	−0.0002 (4)	−0.0007 (3)	0.0024 (4)
C12	0.0207 (5)	0.0312 (6)	0.0220 (4)	0.0025 (4)	−0.0015 (4)	0.0047 (4)

Geometric parameters (Å, º) top

O1—C9	1.3348 (11)	C4—C5	1.3901 (12)
O1—C11	1.4685 (11)	C4—H4A	0.9500
O2—N4	1.2303 (12)	C5—C6	1.3933 (12)
O3—N4	1.2246 (12)	C5—H5A	0.9500
O4—C9	1.2103 (12)	C7—C8	1.3849 (12)
N1—C7	1.3616 (11)	C7—C10	1.4878 (12)
N1—N2	1.3705 (10)	C8—C9	1.4751 (13)
N1—C6	1.4258 (11)	C10—H10A	0.9800
N2—N3	1.3022 (11)	C10—H10B	0.9800
N3—C8	1.3686 (11)	C10—H10C	0.9800
N4—C3	1.4730 (12)	C11—C12	1.5029 (14)
C1—C2	1.3879 (13)	C11—H11A	0.9900
C1—C6	1.3962 (13)	C11—H11B	0.9900
C1—H1A	0.9500	C12—H12A	0.9800
C2—C3	1.3897 (13)	C12—H12B	0.9800
C2—H2A	0.9500	C12—H12C	0.9800
C3—C4	1.3846 (13)

C9—O1—C11	114.50 (8)	N1—C7—C8	103.28 (7)
C7—N1—N2	111.11 (7)	N1—C7—C10	125.27 (8)
C7—N1—C6	131.17 (7)	C8—C7—C10	131.44 (8)
N2—N1—C6	117.71 (7)	N3—C8—C7	109.38 (8)
N3—N2—N1	107.24 (7)	N3—C8—C9	123.56 (8)
N2—N3—C8	108.98 (7)	C7—C8—C9	127.01 (8)
O3—N4—O2	124.49 (9)	O4—C9—O1	125.10 (9)
O3—N4—C3	117.77 (9)	O4—C9—C8	122.48 (8)
O2—N4—C3	117.74 (8)	O1—C9—C8	112.41 (8)
C2—C1—C6	119.36 (8)	C7—C10—H10A	109.5
C2—C1—H1A	120.3	C7—C10—H10B	109.5
C6—C1—H1A	120.3	H10A—C10—H10B	109.5
C1—C2—C3	118.52 (8)	C7—C10—H10C	109.5
C1—C2—H2A	120.7	H10A—C10—H10C	109.5
C3—C2—H2A	120.7	H10B—C10—H10C	109.5
C4—C3—C2	122.51 (8)	O1—C11—C12	107.67 (8)
C4—C3—N4	118.52 (8)	O1—C11—H11A	110.2
C2—C3—N4	118.97 (8)	C12—C11—H11A	110.2
C3—C4—C5	119.11 (8)	O1—C11—H11B	110.2
C3—C4—H4A	120.4	C12—C11—H11B	110.2
C5—C4—H4A	120.4	H11A—C11—H11B	108.5
C4—C5—C6	118.85 (8)	C11—C12—H12A	109.5
C4—C5—H5A	120.6	C11—C12—H12B	109.5
C6—C5—H5A	120.6	H12A—C12—H12B	109.5
C5—C6—C1	121.66 (8)	C11—C12—H12C	109.5
C5—C6—N1	120.02 (8)	H12A—C12—H12C	109.5
C1—C6—N1	118.27 (8)	H12B—C12—H12C	109.5

C7—N1—N2—N3	0.42 (10)	C7—N1—C6—C1	142.62 (10)
C6—N1—N2—N3	179.36 (8)	N2—N1—C6—C1	−36.07 (12)
N1—N2—N3—C8	−0.58 (10)	N2—N1—C7—C8	−0.07 (10)
C6—C1—C2—C3	0.41 (14)	C6—N1—C7—C8	−178.83 (9)
C1—C2—C3—C4	0.58 (14)	N2—N1—C7—C10	179.02 (9)
C1—C2—C3—N4	−179.20 (8)	C6—N1—C7—C10	0.27 (15)
O3—N4—C3—C4	171.06 (9)	N2—N3—C8—C7	0.56 (11)
O2—N4—C3—C4	−8.86 (13)	N2—N3—C8—C9	−177.07 (9)
O3—N4—C3—C2	−9.16 (13)	N1—C7—C8—N3	−0.28 (10)
O2—N4—C3—C2	170.93 (9)	C10—C7—C8—N3	−179.30 (9)
C2—C3—C4—C5	−0.85 (14)	N1—C7—C8—C9	177.24 (9)
N4—C3—C4—C5	178.93 (8)	C10—C7—C8—C9	−1.78 (17)
C3—C4—C5—C6	0.12 (14)	C11—O1—C9—O4	1.16 (14)
C4—C5—C6—C1	0.87 (14)	C11—O1—C9—C8	−179.05 (8)
C4—C5—C6—N1	−176.36 (8)	N3—C8—C9—O4	166.28 (9)
C2—C1—C6—C5	−1.14 (14)	C7—C8—C9—O4	−10.92 (16)
C2—C1—C6—N1	176.14 (8)	N3—C8—C9—O1	−13.51 (13)
C7—N1—C6—C5	−40.05 (14)	C7—C8—C9—O1	169.29 (9)
N2—N1—C6—C5	141.26 (9)	C9—O1—C11—C12	171.11 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···N3ⁱ	0.95	2.59	3.5243 (12)	168
C5—H5A···N2ⁱⁱ	0.95	2.60	3.2347 (12)	125
C5—H5A···N3ⁱⁱ	0.95	2.54	3.4127 (12)	154
C10—H10B···O4	0.98	2.48	3.0936 (12)	120

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₂N₄O₄
M_r	276.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.5309 (3), 7.3014 (2), 12.6058 (3)
β (°)	99.574 (1)
V (Å³)	1228.04 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.50 × 0.16 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.944, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	16800, 4469, 3699
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.759

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.114, 1.03
No. of reflections	4469
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.30

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008), 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
C1—H1A···N3ⁱ	0.95	2.59	3.5243 (12)	168
C5—H5A···N2ⁱⁱ	0.95	2.60	3.2347 (12)	125
C5—H5A···N3ⁱⁱ	0.95	2.54	3.4127 (12)	154
C10—H10B···O4	0.98	2.48	3.0936 (12)	120

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009

§Thomson Reuters ResearcherID: A-5525-2009

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160).

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