supplementary materials


is5313 scheme

Acta Cryst. (2013). E69, o1724    [ doi:10.1107/S1600536813029425 ]

1-[5-Methyl-1-(4-nitro­phen­yl)-1H-1,2,3-triazol-4-yl]ethanone

N. Vinutha, S. Madan Kumar, Nithinchandra, K. Balakrishna, N. K. Lokanath and D. Revannasiddaiah

Abstract top

The asymmetric unit of the title compound, C11H10N4O3, contains two independent mol­ecules in which the benzene rings make dihedral angles of 38.3 (2) and 87.1 (2)° with respect to the triazole rings. In the crystal, the mol­ecules are linked by C-H...O hydrogen bonds, forming chains along [021]. Further, weak C-O...[pi] [3.865 (5) Å, 83.8 (3)°] and N-O...[pi] [3.275 (5) and 3.240 (6) Å, 141.8 (4) and 102.8 (3)°] inter­actions are observed.

Comment top

1,2,3-Triazoles are attractive constructs, because of their unique chemical properties and they find many applications in organic and medicinal chemistry (Nithinchandra et al., 2013). They are found to be potent antimicrobial (Sherement et al., 2004)and antiviral agents. Some of them have exhibited antiproliferative and anti-inflammatory property (Nithinchandra et al., 2012). Also, 1,2,3-triazoles are used as DNA cleaving agents (Manfredini et al., 2000) and potassium channel activators (Biagi et al., 2004).

The asymmetric unit of of the title compound consists of two molecules A and B (Fig. 1). They show conformational difference, as evident from dihedral angles. The dihedral angle between benzene ring and triazole moiety is 38.2 (3)° in A and 87.6 (4)° in B. The values of the bond lengths are similar to the reported literature (Allen et al., 1987).

In the crystal, the molecules are linked to one another with the C—H···O hydrogen bonds (Table 1). Also, short contacts of the type C3A—O1A···Cg4(x + 1/2, y - 1, z) with a distance 3.865 (5) Å [angle 83.8 (3)°], N4A—O2A···Cg3(x - 1, y - 1, z + 1/2) with a distance 3.275 (5) Å [angle 141.8 (4)°] and N4B—O3B···Cg1(x - 1/2, y - 1, z) with a distance 3.240 (6) Å [angle 102.8 (3)°] help in crystal stabilization. These interactions form a three dimensional architecture (Fig. 2), where Cg1, Cg3 and Cg4 are the centroids of the N1A/N2A/N3A/C1A/C2A, N1B/N2B/N3B/C1B/C2B and C6B–C11B rings, respectively.

Related literature top

For chemical and biological properties and pharmocological applications of 1,2,3-triazole derivative, see: Nithinchandra et al. (2012, 2013); Biagi et al. (2004); Manfredini et al. (2000); Sherement et al. (2004). For bond-length data, see: Allen et al. (1987).

Experimental top

1-Azido-4-nitrobenzene (0.01 mol) was treated with acetyl acetone (0.01 mol) in methanol (10 ml) and the mixture was cooled to 0 °C. Sodium methoxide (0.01 mol) 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/petroleum ether, 2:3, v/v). After completion of the reaction, the mixture was poured onto ice cold water. The precipitated solid was filtered, washed with water and recrystallized from ethanol. Single crystals suitable for X-ray analysis were obtained from a 1:2 mixture of DMF and ethanol by slow evaporation.

Refinement top

All the H atoms were fixed geometrically (C—H = 0.93–0.96 Å) and allowed to ride on their parent atoms with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C) for other H atoms. The Flack parameter x refines to 0.2 (4) with unmerged data, and the absolute structure cannot be determined reliably. The final refinement was performed with the merged data.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).

Figures top
[Figure 1] Fig. 1. Asymmetric unit of the title compound with 50% probability ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the title compound, viewed along the b axis. Dotted lines indicate hydrogen bonds and short contacts involved.
1-[5-Methyl-1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl]ethanone top
Crystal data top
C11H10N4O3F(000) = 1024
Mr = 246.23Dx = 1.435 Mg m3
Orthorhombic, Pca21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2acCell parameters from 1910 reflections
a = 7.2786 (10) Åθ = 3.2–64.2°
b = 11.5055 (16) ŵ = 0.91 mm1
c = 27.220 (4) ÅT = 296 K
V = 2279.5 (6) Å3Block, red
Z = 80.23 × 0.22 × 0.21 mm
Data collection top
Bruker X8 Proteum
diffractometer
1910 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode1617 reflections with I > 2σ(I)
Helios multilayer optics monochromatorRint = 0.057
Detector resolution: 10.7 pixels mm-1θmax = 64.2°, θmin = 3.3°
φ and ω scansh = 88
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
k = 513
Tmin = 0.818, Tmax = 0.831l = 3031
8697 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0932P)2]
where P = (Fo2 + 2Fc2)/3
1910 reflections(Δ/σ)max < 0.001
329 parametersΔρmax = 0.17 e Å3
1 restraintΔρmin = 0.17 e Å3
Crystal data top
C11H10N4O3V = 2279.5 (6) Å3
Mr = 246.23Z = 8
Orthorhombic, Pca21Cu Kα radiation
a = 7.2786 (10) ŵ = 0.91 mm1
b = 11.5055 (16) ÅT = 296 K
c = 27.220 (4) Å0.23 × 0.22 × 0.21 mm
Data collection top
Bruker X8 Proteum
diffractometer
1910 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
1617 reflections with I > 2σ(I)
Tmin = 0.818, Tmax = 0.831Rint = 0.057
8697 measured reflectionsθmax = 64.2°
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.138Δρmax = 0.17 e Å3
S = 1.08Δρmin = 0.17 e Å3
1910 reflectionsAbsolute structure: ?
329 parametersAbsolute structure parameter: ?
1 restraintRogers parameter: ?
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
xyzUiso*/Ueq
O1A0.1681 (6)0.7317 (4)0.30010 (16)0.0907 (16)
O2A0.5412 (8)0.8545 (4)0.64933 (16)0.1063 (18)
O3A0.4670 (10)1.0325 (5)0.64815 (18)0.129 (3)
N1A0.4033 (6)0.9759 (4)0.35049 (15)0.0680 (16)
N2A0.4450 (6)0.9990 (4)0.39568 (14)0.0657 (14)
N3A0.3707 (5)0.9122 (3)0.42410 (12)0.0522 (11)
N4A0.4913 (7)0.9402 (4)0.62761 (15)0.0767 (16)
C1A0.2812 (6)0.8331 (4)0.39621 (15)0.0497 (12)
C2A0.3036 (6)0.8752 (4)0.34871 (16)0.0570 (14)
C3A0.2316 (7)0.8288 (5)0.30239 (18)0.0670 (16)
C4A0.2355 (10)0.9058 (6)0.2585 (2)0.084 (2)
C5A0.1735 (7)0.7346 (4)0.41484 (19)0.0667 (17)
C6A0.3986 (6)0.9188 (4)0.47594 (15)0.0503 (14)
C7A0.3940 (7)1.0257 (4)0.49864 (17)0.0603 (17)
C8A0.4254 (7)1.0344 (4)0.54869 (16)0.0633 (17)
C9A0.4592 (7)0.9331 (4)0.57459 (16)0.0587 (14)
C10A0.4634 (7)0.8257 (4)0.55236 (16)0.0600 (16)
C11A0.4341 (6)0.8185 (4)0.50253 (16)0.0577 (16)
O1B0.0706 (6)0.3153 (4)0.04016 (14)0.0883 (16)
O2B0.0771 (8)0.4308 (5)0.40221 (15)0.110 (2)
O3B0.1969 (7)0.2600 (5)0.40198 (14)0.0950 (18)
N1B0.3210 (5)0.4147 (4)0.10651 (14)0.0653 (14)
N2B0.3525 (5)0.4112 (4)0.15379 (13)0.0637 (14)
N3B0.1961 (5)0.3690 (3)0.17486 (12)0.0538 (11)
N4B0.1456 (6)0.3479 (5)0.38102 (15)0.0733 (18)
C1B0.0636 (6)0.3448 (4)0.14185 (17)0.0550 (12)
C2B0.1480 (6)0.3740 (4)0.09745 (16)0.0550 (12)
C3B0.0683 (7)0.3710 (4)0.04782 (15)0.0597 (16)
C4B0.1636 (9)0.4365 (6)0.00848 (19)0.082 (2)
C5B0.1210 (8)0.3025 (5)0.1540 (2)0.0760 (19)
C6B0.1834 (6)0.3626 (4)0.22757 (15)0.0533 (14)
C7B0.2290 (8)0.2619 (4)0.25147 (17)0.0673 (16)
C8B0.2177 (7)0.2566 (4)0.30211 (19)0.0693 (17)
C9B0.1605 (6)0.3519 (5)0.32681 (16)0.0570 (14)
C10B0.1174 (7)0.4558 (5)0.30392 (19)0.0703 (17)
C11B0.1287 (8)0.4607 (5)0.25360 (18)0.0680 (17)
H5A10.248800.666100.415300.1000*
H7A0.369701.092200.480300.0730*
H5A20.069500.721800.393800.1000*
H8A0.423901.106200.564400.0760*
H5A30.131800.751400.447500.1000*
H4A10.171800.868900.231900.1260*
H10A0.485600.759000.570700.0720*
H4A20.360600.920100.249200.1260*
H11A0.438100.746900.486800.0690*
H4A30.176600.978200.266200.1260*
H5B10.132900.223000.143800.1140*
H5B20.211000.349100.137400.1140*
H5B30.139800.307700.188900.1140*
H4B10.283000.403400.003100.1230*
H4B20.176400.516300.018200.1230*
H4B30.093100.432100.021300.1230*
H7B0.267300.197200.233700.0800*
H8B0.248900.188900.318800.0830*
H10B0.081700.520400.322100.0840*
H11B0.100100.529100.237100.0820*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.115 (3)0.074 (3)0.083 (2)0.011 (2)0.018 (2)0.0103 (19)
O2A0.146 (4)0.107 (3)0.066 (2)0.015 (3)0.021 (3)0.008 (2)
O3A0.217 (7)0.099 (3)0.071 (3)0.001 (4)0.007 (3)0.018 (2)
N1A0.081 (3)0.067 (3)0.056 (2)0.010 (2)0.0006 (19)0.0059 (19)
N2A0.080 (3)0.063 (2)0.054 (2)0.017 (2)0.0022 (18)0.0112 (18)
N3A0.0547 (19)0.050 (2)0.0518 (19)0.0050 (16)0.0006 (14)0.0012 (15)
N4A0.092 (3)0.081 (3)0.057 (2)0.005 (3)0.003 (2)0.002 (2)
C1A0.053 (2)0.044 (2)0.052 (2)0.0033 (18)0.0018 (18)0.0026 (17)
C2A0.062 (2)0.056 (3)0.053 (2)0.002 (2)0.000 (2)0.004 (2)
C3A0.073 (3)0.070 (3)0.058 (2)0.011 (3)0.005 (2)0.003 (2)
C4A0.107 (4)0.093 (4)0.051 (2)0.004 (3)0.001 (3)0.006 (3)
C5A0.075 (3)0.060 (3)0.065 (3)0.009 (2)0.002 (2)0.007 (2)
C6A0.051 (2)0.055 (3)0.045 (2)0.0043 (18)0.0043 (17)0.0041 (18)
C7A0.066 (3)0.055 (3)0.060 (3)0.001 (2)0.002 (2)0.005 (2)
C8A0.075 (3)0.058 (3)0.057 (3)0.004 (2)0.004 (2)0.006 (2)
C9A0.059 (2)0.069 (3)0.048 (2)0.002 (2)0.0011 (18)0.000 (2)
C10A0.066 (3)0.060 (3)0.054 (2)0.001 (2)0.001 (2)0.007 (2)
C11A0.064 (3)0.052 (3)0.057 (2)0.002 (2)0.0023 (19)0.0002 (19)
O1B0.110 (3)0.092 (3)0.063 (2)0.039 (2)0.0193 (19)0.0015 (18)
O2B0.139 (4)0.130 (4)0.061 (3)0.005 (3)0.017 (2)0.022 (2)
O3B0.105 (3)0.123 (4)0.057 (2)0.018 (3)0.003 (2)0.018 (2)
N1B0.069 (2)0.076 (3)0.051 (2)0.0069 (19)0.0015 (18)0.0005 (18)
N2B0.060 (2)0.084 (3)0.0470 (19)0.012 (2)0.0031 (16)0.0026 (18)
N3B0.058 (2)0.055 (2)0.0485 (19)0.0005 (17)0.0001 (15)0.0000 (15)
N4B0.074 (3)0.099 (4)0.047 (2)0.019 (3)0.0022 (19)0.004 (2)
C1B0.062 (2)0.050 (2)0.053 (2)0.0065 (19)0.0007 (18)0.0003 (18)
C2B0.060 (2)0.053 (2)0.052 (2)0.0023 (18)0.0045 (19)0.0005 (18)
C3B0.076 (3)0.054 (3)0.049 (2)0.003 (2)0.003 (2)0.0024 (19)
C4B0.090 (4)0.105 (5)0.050 (2)0.010 (3)0.002 (3)0.007 (3)
C5B0.072 (3)0.088 (4)0.068 (3)0.023 (3)0.006 (2)0.007 (3)
C6B0.060 (2)0.059 (3)0.041 (2)0.000 (2)0.0024 (17)0.0021 (18)
C7B0.090 (3)0.059 (3)0.053 (2)0.009 (2)0.004 (2)0.004 (2)
C8B0.084 (3)0.065 (3)0.059 (3)0.006 (3)0.004 (2)0.011 (2)
C9B0.055 (2)0.072 (3)0.044 (2)0.010 (2)0.0004 (17)0.000 (2)
C10B0.082 (3)0.070 (3)0.059 (3)0.005 (3)0.003 (2)0.012 (2)
C11B0.089 (3)0.060 (3)0.055 (3)0.009 (3)0.002 (2)0.000 (2)
Geometric parameters (Å, º) top
O1A—C3A1.211 (7)C4A—H4A20.9600
O2A—N4A1.206 (7)C4A—H4A30.9600
O3A—N4A1.213 (7)C5A—H5A30.9600
O1B—C3B1.215 (7)C5A—H5A20.9600
O2B—N4B1.221 (8)C5A—H5A10.9600
O3B—N4B1.220 (8)C7A—H7A0.9300
N1A—N2A1.295 (6)C8A—H8A0.9300
N1A—C2A1.368 (6)C10A—H10A0.9300
N2A—N3A1.374 (6)C11A—H11A0.9300
N3A—C1A1.352 (6)C1B—C2B1.397 (6)
N3A—C6A1.428 (5)C1B—C5B1.467 (7)
N4A—C9A1.464 (6)C2B—C3B1.471 (6)
N1B—N2B1.308 (5)C3B—C4B1.482 (7)
N1B—C2B1.366 (6)C6B—C7B1.370 (6)
N2B—N3B1.364 (5)C6B—C11B1.391 (7)
N3B—C1B1.347 (6)C7B—C8B1.382 (7)
N3B—C6B1.440 (5)C8B—C9B1.352 (7)
N4B—C9B1.480 (6)C9B—C10B1.384 (8)
C1A—C5A1.468 (7)C10B—C11B1.373 (7)
C1A—C2A1.390 (6)C4B—H4B10.9600
C2A—C3A1.466 (7)C4B—H4B20.9600
C3A—C4A1.488 (8)C4B—H4B30.9600
C6A—C7A1.377 (6)C5B—H5B10.9600
C6A—C11A1.387 (6)C5B—H5B20.9600
C7A—C8A1.385 (6)C5B—H5B30.9600
C8A—C9A1.384 (6)C7B—H7B0.9300
C9A—C10A1.376 (6)C8B—H8B0.9300
C10A—C11A1.376 (6)C10B—H10B0.9300
C4A—H4A10.9600C11B—H11B0.9300
N2A—N1A—C2A109.4 (4)C8A—C7A—H7A120.00
N1A—N2A—N3A107.1 (4)C6A—C7A—H7A120.00
N2A—N3A—C1A111.3 (3)C9A—C8A—H8A121.00
N2A—N3A—C6A117.5 (3)C7A—C8A—H8A121.00
C1A—N3A—C6A131.2 (4)C9A—C10A—H10A121.00
O2A—N4A—O3A122.3 (5)C11A—C10A—H10A120.00
O2A—N4A—C9A119.1 (4)C6A—C11A—H11A120.00
O3A—N4A—C9A118.7 (5)C10A—C11A—H11A120.00
N2B—N1B—C2B109.2 (4)N3B—C1B—C2B102.3 (4)
N1B—N2B—N3B106.2 (3)N3B—C1B—C5B125.0 (4)
N2B—N3B—C1B113.0 (3)C2B—C1B—C5B132.7 (4)
N2B—N3B—C6B119.4 (3)N1B—C2B—C1B109.4 (4)
C1B—N3B—C6B127.5 (4)N1B—C2B—C3B122.5 (4)
O3B—N4B—C9B118.0 (5)C1B—C2B—C3B128.0 (4)
O2B—N4B—O3B123.5 (4)O1B—C3B—C2B119.9 (4)
O2B—N4B—C9B118.5 (5)O1B—C3B—C4B122.3 (4)
N3A—C1A—C5A125.6 (4)C2B—C3B—C4B117.9 (4)
C2A—C1A—C5A130.7 (4)N3B—C6B—C7B120.1 (4)
N3A—C1A—C2A103.4 (4)N3B—C6B—C11B119.0 (4)
N1A—C2A—C1A108.9 (4)C7B—C6B—C11B120.9 (4)
N1A—C2A—C3A121.9 (4)C6B—C7B—C8B119.8 (4)
C1A—C2A—C3A129.1 (4)C7B—C8B—C9B118.6 (4)
O1A—C3A—C2A121.1 (5)N4B—C9B—C8B119.5 (5)
O1A—C3A—C4A121.0 (5)N4B—C9B—C10B117.3 (5)
C2A—C3A—C4A117.8 (5)C8B—C9B—C10B123.1 (4)
N3A—C6A—C11A119.9 (4)C9B—C10B—C11B118.1 (5)
N3A—C6A—C7A119.2 (4)C6B—C11B—C10B119.5 (5)
C7A—C6A—C11A120.9 (4)C3B—C4B—H4B1109.00
C6A—C7A—C8A120.1 (4)C3B—C4B—H4B2109.00
C7A—C8A—C9A118.0 (4)C3B—C4B—H4B3109.00
C8A—C9A—C10A122.4 (4)H4B1—C4B—H4B2109.00
N4A—C9A—C8A118.9 (4)H4B1—C4B—H4B3110.00
N4A—C9A—C10A118.7 (4)H4B2—C4B—H4B3110.00
C9A—C10A—C11A119.0 (4)C1B—C5B—H5B1109.00
C6A—C11A—C10A119.6 (4)C1B—C5B—H5B2109.00
C3A—C4A—H4A1109.00C1B—C5B—H5B3109.00
C3A—C4A—H4A2109.00H5B1—C5B—H5B2110.00
H4A1—C4A—H4A2110.00H5B1—C5B—H5B3109.00
H4A1—C4A—H4A3109.00H5B2—C5B—H5B3109.00
C3A—C4A—H4A3109.00C6B—C7B—H7B120.00
H4A2—C4A—H4A3109.00C8B—C7B—H7B120.00
C1A—C5A—H5A1109.00C7B—C8B—H8B121.00
C1A—C5A—H5A2109.00C9B—C8B—H8B121.00
C1A—C5A—H5A3109.00C9B—C10B—H10B121.00
H5A1—C5A—H5A2109.00C11B—C10B—H10B121.00
H5A1—C5A—H5A3110.00C6B—C11B—H11B120.00
H5A2—C5A—H5A3110.00C10B—C11B—H11B120.00
C2A—N1A—N2A—N3A0.3 (5)N3A—C1A—C2A—C3A177.7 (5)
N2A—N1A—C2A—C1A0.3 (5)C5A—C1A—C2A—C3A3.4 (8)
N2A—N1A—C2A—C3A178.0 (4)C5A—C1A—C2A—N1A174.2 (5)
N1A—N2A—N3A—C1A0.2 (5)C1A—C2A—C3A—O1A14.0 (8)
N1A—N2A—N3A—C6A180.0 (4)C1A—C2A—C3A—C4A164.8 (5)
N2A—N3A—C1A—C2A0.0 (5)N1A—C2A—C3A—C4A12.5 (7)
N2A—N3A—C1A—C5A174.7 (4)N1A—C2A—C3A—O1A168.8 (5)
C6A—N3A—C1A—C2A179.9 (4)N3A—C6A—C11A—C10A179.1 (4)
C6A—N3A—C1A—C5A5.4 (7)N3A—C6A—C7A—C8A178.3 (4)
N2A—N3A—C6A—C7A37.8 (6)C11A—C6A—C7A—C8A0.1 (7)
N2A—N3A—C6A—C11A140.7 (4)C7A—C6A—C11A—C10A0.6 (7)
C1A—N3A—C6A—C7A142.4 (5)C6A—C7A—C8A—C9A0.6 (7)
C1A—N3A—C6A—C11A39.1 (7)C7A—C8A—C9A—C10A0.3 (8)
O2A—N4A—C9A—C8A171.7 (5)C7A—C8A—C9A—N4A179.5 (5)
O2A—N4A—C9A—C10A8.5 (8)N4A—C9A—C10A—C11A179.7 (4)
O3A—N4A—C9A—C8A8.2 (8)C8A—C9A—C10A—C11A0.4 (8)
O3A—N4A—C9A—C10A171.7 (6)C9A—C10A—C11A—C6A0.9 (7)
C2B—N1B—N2B—N3B0.7 (5)N3B—C1B—C2B—N1B0.9 (5)
N2B—N1B—C2B—C1B1.1 (6)N3B—C1B—C2B—C3B177.2 (4)
N2B—N1B—C2B—C3B177.6 (4)C5B—C1B—C2B—N1B177.0 (5)
N1B—N2B—N3B—C6B175.6 (4)C5B—C1B—C2B—C3B0.7 (9)
N1B—N2B—N3B—C1B0.2 (5)N1B—C2B—C3B—O1B166.6 (5)
N2B—N3B—C1B—C2B0.5 (5)N1B—C2B—C3B—C4B12.9 (7)
N2B—N3B—C1B—C5B177.6 (5)C1B—C2B—C3B—O1B17.6 (8)
C1B—N3B—C6B—C11B90.7 (6)C1B—C2B—C3B—C4B162.9 (5)
C6B—N3B—C1B—C5B2.3 (7)N3B—C6B—C7B—C8B179.6 (4)
N2B—N3B—C6B—C7B94.0 (5)C11B—C6B—C7B—C8B1.1 (8)
C6B—N3B—C1B—C2B175.9 (4)N3B—C6B—C11B—C10B179.5 (5)
C1B—N3B—C6B—C7B90.9 (6)C7B—C6B—C11B—C10B1.1 (8)
N2B—N3B—C6B—C11B84.5 (5)C6B—C7B—C8B—C9B0.3 (8)
O3B—N4B—C9B—C8B4.5 (7)C7B—C8B—C9B—N4B179.4 (5)
O2B—N4B—C9B—C10B8.1 (7)C7B—C8B—C9B—C10B1.8 (8)
O2B—N4B—C9B—C8B173.1 (5)N4B—C9B—C10B—C11B179.4 (5)
O3B—N4B—C9B—C10B174.3 (5)C8B—C9B—C10B—C11B1.9 (8)
N3A—C1A—C2A—N1A0.2 (5)C9B—C10B—C11B—C6B0.4 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5B—H5B1···O3Ai0.962.513.306 (8)141
C10B—H10B···O1A0.932.583.197 (7)124
Symmetry code: (i) x+1/2, y1, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5B—H5B1···O3Ai0.962.513.306 (8)141
C10B—H10B···O1A0.932.583.197 (7)124
Symmetry code: (i) x+1/2, y1, z1/2.
Acknowledgements top

The authors are thankful to the IOE, University of Mysore, for providing the single-crystal X-ray diffraction facility. VN is grateful to the UGC for the award of an RFSMS Fellowship. RD acknowledges the UGC, New Delhi, for financial support under the Major Research Project Scheme [UGC MRP No. F.41–882/2012 (SR) dated 01/07/2012].

references
References top

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Prpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Biagi, G., Calderone, V., Giorgi, I., Livi, O., Martinotti, E., Martelli, A. & Nardi, A. (2004). Farmaco, 59, 397–404.

Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.

Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.

Manfredini, S., Vicentini, C. B., Manfrini, M., Bianchi, N., Rutigliano, C., Mischiati, C. & Gambari, R. (2000). Bioorg. Med. Chem. 8, 2343–2346.

Nithinchandra, Kalluraya, B., Aamir, S. & Shabaraya, A. R. (2012). Eur. J. Med. Chem. 54, 597–604.

Nithinchandra, Kalluraya, B., Shobhitha, S. & Babu, M. (2013). J. Chem. Pharm. Res. 5, 307–313.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Sherement, E. A., Tomanov, R. I., Trukhin, E. V. & Berestovitskaya, V. M. (2004). Russ. J. Org. Chem. 40, 594–595.