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

The asymmetric unit of the title compound, C11H10N4O3, contains two independent mol-ecules 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 mol-ecules are linked by C-H⋯O hydrogen bonds, forming chains along [021]. Further, weak C-O⋯π [3.865 (5) Å, 83.8 (3)°] and N-O⋯π [3.275 (5) and 3.240 (6) Å, 141.8 (4) and 102.8 (3)°] inter-actions are observed.

Related literature

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

Crystal data

C11H10N4O3

M = 246.23

Orthorhombic,

a = 7.2786 (10) Å

b = 11.5055 (16) Å

c = 27.220 (4) Å

V = 2279.5 (6) Å3

Z = 8

Cu Kα radiation

μ = 0.91 mm−1

T = 296 K

0.23 × 0.22 × 0.21 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.818, T max = 0.831

8697 measured reflections

1910 independent reflections

1617 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.138

S = 1.08

1910 reflections

329 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813029425/is5313sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813029425/is5313Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H10N4O3	F(000) = 1024
Mr = 246.23	Dx = 1.435 Mg m−3
Orthorhombic, Pca21	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2ac	Cell parameters from 1910 reflections
a = 7.2786 (10) Å	θ = 3.2–64.2°
b = 11.5055 (16) Å	µ = 0.91 mm−1
c = 27.220 (4) Å	T = 296 K
V = 2279.5 (6) Å3	Block, red
Z = 8	0.23 × 0.22 × 0.21 mm

Bruker X8 Proteum diffractometer	1910 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	1617 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.057
Detector resolution: 10.7 pixels mm-1	θmax = 64.2°, θmin = 3.3°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −5→13
Tmin = 0.818, Tmax = 0.831	l = −30→31
8697 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-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 parameters	Δρmax = 0.17 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1A	0.1681 (6)	0.7317 (4)	0.30010 (16)	0.0907 (16)
O2A	0.5412 (8)	0.8545 (4)	0.64933 (16)	0.1063 (18)
O3A	0.4670 (10)	1.0325 (5)	0.64815 (18)	0.129 (3)
N1A	0.4033 (6)	0.9759 (4)	0.35049 (15)	0.0680 (16)
N2A	0.4450 (6)	0.9990 (4)	0.39568 (14)	0.0657 (14)
N3A	0.3707 (5)	0.9122 (3)	0.42410 (12)	0.0522 (11)
N4A	0.4913 (7)	0.9402 (4)	0.62761 (15)	0.0767 (16)
C1A	0.2812 (6)	0.8331 (4)	0.39621 (15)	0.0497 (12)
C2A	0.3036 (6)	0.8752 (4)	0.34871 (16)	0.0570 (14)
C3A	0.2316 (7)	0.8288 (5)	0.30239 (18)	0.0670 (16)
C4A	0.2355 (10)	0.9058 (6)	0.2585 (2)	0.084 (2)
C5A	0.1735 (7)	0.7346 (4)	0.41484 (19)	0.0667 (17)
C6A	0.3986 (6)	0.9188 (4)	0.47594 (15)	0.0503 (14)
C7A	0.3940 (7)	1.0257 (4)	0.49864 (17)	0.0603 (17)
C8A	0.4254 (7)	1.0344 (4)	0.54869 (16)	0.0633 (17)
C9A	0.4592 (7)	0.9331 (4)	0.57459 (16)	0.0587 (14)
C10A	0.4634 (7)	0.8257 (4)	0.55236 (16)	0.0600 (16)
C11A	0.4341 (6)	0.8185 (4)	0.50253 (16)	0.0577 (16)
O1B	−0.0706 (6)	0.3153 (4)	0.04016 (14)	0.0883 (16)
O2B	0.0771 (8)	0.4308 (5)	0.40221 (15)	0.110 (2)
O3B	0.1969 (7)	0.2600 (5)	0.40198 (14)	0.0950 (18)
N1B	0.3210 (5)	0.4147 (4)	0.10651 (14)	0.0653 (14)
N2B	0.3525 (5)	0.4112 (4)	0.15379 (13)	0.0637 (14)
N3B	0.1961 (5)	0.3690 (3)	0.17486 (12)	0.0538 (11)
N4B	0.1456 (6)	0.3479 (5)	0.38102 (15)	0.0733 (18)
C1B	0.0636 (6)	0.3448 (4)	0.14185 (17)	0.0550 (12)
C2B	0.1480 (6)	0.3740 (4)	0.09745 (16)	0.0550 (12)
C3B	0.0683 (7)	0.3710 (4)	0.04782 (15)	0.0597 (16)
C4B	0.1636 (9)	0.4365 (6)	0.00848 (19)	0.082 (2)
C5B	−0.1210 (8)	0.3025 (5)	0.1540 (2)	0.0760 (19)
C6B	0.1834 (6)	0.3626 (4)	0.22757 (15)	0.0533 (14)
C7B	0.2290 (8)	0.2619 (4)	0.25147 (17)	0.0673 (16)
C8B	0.2177 (7)	0.2566 (4)	0.30211 (19)	0.0693 (17)
C9B	0.1605 (6)	0.3519 (5)	0.32681 (16)	0.0570 (14)
C10B	0.1174 (7)	0.4558 (5)	0.30392 (19)	0.0703 (17)
C11B	0.1287 (8)	0.4607 (5)	0.25360 (18)	0.0680 (17)
H5A1	0.24880	0.66610	0.41530	0.1000*
H7A	0.36970	1.09220	0.48030	0.0730*
H5A2	0.06950	0.72180	0.39380	0.1000*
H8A	0.42390	1.10620	0.56440	0.0760*
H5A3	0.13180	0.75140	0.44750	0.1000*
H4A1	0.17180	0.86890	0.23190	0.1260*
H10A	0.48560	0.75900	0.57070	0.0720*
H4A2	0.36060	0.92010	0.24920	0.1260*
H11A	0.43810	0.74690	0.48680	0.0690*
H4A3	0.17660	0.97820	0.26620	0.1260*
H5B1	−0.13290	0.22300	0.14380	0.1140*
H5B2	−0.21100	0.34910	0.13740	0.1140*
H5B3	−0.13980	0.30770	0.18890	0.1140*
H4B1	0.28300	0.40340	0.00310	0.1230*
H4B2	0.17640	0.51630	0.01820	0.1230*
H4B3	0.09310	0.43210	−0.02130	0.1230*
H7B	0.26730	0.19720	0.23370	0.0800*
H8B	0.24890	0.18890	0.31880	0.0830*
H10B	0.08170	0.52040	0.32210	0.0840*
H11B	0.10010	0.52910	0.23710	0.0820*

	U11	U22	U33	U12	U13	U23
O1A	0.115 (3)	0.074 (3)	0.083 (2)	−0.011 (2)	−0.018 (2)	−0.0103 (19)
O2A	0.146 (4)	0.107 (3)	0.066 (2)	0.015 (3)	−0.021 (3)	0.008 (2)
O3A	0.217 (7)	0.099 (3)	0.071 (3)	−0.001 (4)	−0.007 (3)	−0.018 (2)
N1A	0.081 (3)	0.067 (3)	0.056 (2)	−0.010 (2)	0.0006 (19)	0.0059 (19)
N2A	0.080 (3)	0.063 (2)	0.054 (2)	−0.017 (2)	0.0022 (18)	0.0112 (18)
N3A	0.0547 (19)	0.050 (2)	0.0518 (19)	−0.0050 (16)	0.0006 (14)	0.0012 (15)
N4A	0.092 (3)	0.081 (3)	0.057 (2)	−0.005 (3)	−0.003 (2)	−0.002 (2)
C1A	0.053 (2)	0.044 (2)	0.052 (2)	0.0033 (18)	−0.0018 (18)	0.0026 (17)
C2A	0.062 (2)	0.056 (3)	0.053 (2)	0.002 (2)	0.000 (2)	0.004 (2)
C3A	0.073 (3)	0.070 (3)	0.058 (2)	0.011 (3)	−0.005 (2)	−0.003 (2)
C4A	0.107 (4)	0.093 (4)	0.051 (2)	0.004 (3)	0.001 (3)	0.006 (3)
C5A	0.075 (3)	0.060 (3)	0.065 (3)	−0.009 (2)	0.002 (2)	0.007 (2)
C6A	0.051 (2)	0.055 (3)	0.045 (2)	−0.0043 (18)	0.0043 (17)	0.0041 (18)
C7A	0.066 (3)	0.055 (3)	0.060 (3)	−0.001 (2)	−0.002 (2)	0.005 (2)
C8A	0.075 (3)	0.058 (3)	0.057 (3)	−0.004 (2)	0.004 (2)	−0.006 (2)
C9A	0.059 (2)	0.069 (3)	0.048 (2)	−0.002 (2)	0.0011 (18)	0.000 (2)
C10A	0.066 (3)	0.060 (3)	0.054 (2)	−0.001 (2)	−0.001 (2)	0.007 (2)
C11A	0.064 (3)	0.052 (3)	0.057 (2)	0.002 (2)	−0.0023 (19)	0.0002 (19)
O1B	0.110 (3)	0.092 (3)	0.063 (2)	−0.039 (2)	−0.0193 (19)	0.0015 (18)
O2B	0.139 (4)	0.130 (4)	0.061 (3)	0.005 (3)	0.017 (2)	−0.022 (2)
O3B	0.105 (3)	0.123 (4)	0.057 (2)	−0.018 (3)	−0.003 (2)	0.018 (2)
N1B	0.069 (2)	0.076 (3)	0.051 (2)	−0.0069 (19)	0.0015 (18)	0.0005 (18)
N2B	0.060 (2)	0.084 (3)	0.0470 (19)	−0.012 (2)	0.0031 (16)	0.0026 (18)
N3B	0.058 (2)	0.055 (2)	0.0485 (19)	−0.0005 (17)	−0.0001 (15)	0.0000 (15)
N4B	0.074 (3)	0.099 (4)	0.047 (2)	−0.019 (3)	−0.0022 (19)	−0.004 (2)
C1B	0.062 (2)	0.050 (2)	0.053 (2)	−0.0065 (19)	0.0007 (18)	−0.0003 (18)
C2B	0.060 (2)	0.053 (2)	0.052 (2)	−0.0023 (18)	0.0045 (19)	0.0005 (18)
C3B	0.076 (3)	0.054 (3)	0.049 (2)	−0.003 (2)	−0.003 (2)	−0.0024 (19)
C4B	0.090 (4)	0.105 (5)	0.050 (2)	−0.010 (3)	0.002 (3)	0.007 (3)
C5B	0.072 (3)	0.088 (4)	0.068 (3)	−0.023 (3)	0.006 (2)	0.007 (3)
C6B	0.060 (2)	0.059 (3)	0.041 (2)	0.000 (2)	0.0024 (17)	−0.0021 (18)
C7B	0.090 (3)	0.059 (3)	0.053 (2)	0.009 (2)	0.004 (2)	0.004 (2)
C8B	0.084 (3)	0.065 (3)	0.059 (3)	0.006 (3)	0.004 (2)	0.011 (2)
C9B	0.055 (2)	0.072 (3)	0.044 (2)	−0.010 (2)	0.0004 (17)	0.000 (2)
C10B	0.082 (3)	0.070 (3)	0.059 (3)	0.005 (3)	0.003 (2)	−0.012 (2)
C11B	0.089 (3)	0.060 (3)	0.055 (3)	0.009 (3)	0.002 (2)	0.000 (2)

O1A—C3A	1.211 (7)	C4A—H4A2	0.9600
O2A—N4A	1.206 (7)	C4A—H4A3	0.9600
O3A—N4A	1.213 (7)	C5A—H5A3	0.9600
O1B—C3B	1.215 (7)	C5A—H5A2	0.9600
O2B—N4B	1.221 (8)	C5A—H5A1	0.9600
O3B—N4B	1.220 (8)	C7A—H7A	0.9300
N1A—N2A	1.295 (6)	C8A—H8A	0.9300
N1A—C2A	1.368 (6)	C10A—H10A	0.9300
N2A—N3A	1.374 (6)	C11A—H11A	0.9300
N3A—C1A	1.352 (6)	C1B—C2B	1.397 (6)
N3A—C6A	1.428 (5)	C1B—C5B	1.467 (7)
N4A—C9A	1.464 (6)	C2B—C3B	1.471 (6)
N1B—N2B	1.308 (5)	C3B—C4B	1.482 (7)
N1B—C2B	1.366 (6)	C6B—C7B	1.370 (6)
N2B—N3B	1.364 (5)	C6B—C11B	1.391 (7)
N3B—C1B	1.347 (6)	C7B—C8B	1.382 (7)
N3B—C6B	1.440 (5)	C8B—C9B	1.352 (7)
N4B—C9B	1.480 (6)	C9B—C10B	1.384 (8)
C1A—C5A	1.468 (7)	C10B—C11B	1.373 (7)
C1A—C2A	1.390 (6)	C4B—H4B1	0.9600
C2A—C3A	1.466 (7)	C4B—H4B2	0.9600
C3A—C4A	1.488 (8)	C4B—H4B3	0.9600
C6A—C7A	1.377 (6)	C5B—H5B1	0.9600
C6A—C11A	1.387 (6)	C5B—H5B2	0.9600
C7A—C8A	1.385 (6)	C5B—H5B3	0.9600
C8A—C9A	1.384 (6)	C7B—H7B	0.9300
C9A—C10A	1.376 (6)	C8B—H8B	0.9300
C10A—C11A	1.376 (6)	C10B—H10B	0.9300
C4A—H4A1	0.9600	C11B—H11B	0.9300
N2A—N1A—C2A	109.4 (4)	C8A—C7A—H7A	120.00
N1A—N2A—N3A	107.1 (4)	C6A—C7A—H7A	120.00
N2A—N3A—C1A	111.3 (3)	C9A—C8A—H8A	121.00
N2A—N3A—C6A	117.5 (3)	C7A—C8A—H8A	121.00
C1A—N3A—C6A	131.2 (4)	C9A—C10A—H10A	121.00
O2A—N4A—O3A	122.3 (5)	C11A—C10A—H10A	120.00
O2A—N4A—C9A	119.1 (4)	C6A—C11A—H11A	120.00
O3A—N4A—C9A	118.7 (5)	C10A—C11A—H11A	120.00
N2B—N1B—C2B	109.2 (4)	N3B—C1B—C2B	102.3 (4)
N1B—N2B—N3B	106.2 (3)	N3B—C1B—C5B	125.0 (4)
N2B—N3B—C1B	113.0 (3)	C2B—C1B—C5B	132.7 (4)
N2B—N3B—C6B	119.4 (3)	N1B—C2B—C1B	109.4 (4)
C1B—N3B—C6B	127.5 (4)	N1B—C2B—C3B	122.5 (4)
O3B—N4B—C9B	118.0 (5)	C1B—C2B—C3B	128.0 (4)
O2B—N4B—O3B	123.5 (4)	O1B—C3B—C2B	119.9 (4)
O2B—N4B—C9B	118.5 (5)	O1B—C3B—C4B	122.3 (4)
N3A—C1A—C5A	125.6 (4)	C2B—C3B—C4B	117.9 (4)
C2A—C1A—C5A	130.7 (4)	N3B—C6B—C7B	120.1 (4)
N3A—C1A—C2A	103.4 (4)	N3B—C6B—C11B	119.0 (4)
N1A—C2A—C1A	108.9 (4)	C7B—C6B—C11B	120.9 (4)
N1A—C2A—C3A	121.9 (4)	C6B—C7B—C8B	119.8 (4)
C1A—C2A—C3A	129.1 (4)	C7B—C8B—C9B	118.6 (4)
O1A—C3A—C2A	121.1 (5)	N4B—C9B—C8B	119.5 (5)
O1A—C3A—C4A	121.0 (5)	N4B—C9B—C10B	117.3 (5)
C2A—C3A—C4A	117.8 (5)	C8B—C9B—C10B	123.1 (4)
N3A—C6A—C11A	119.9 (4)	C9B—C10B—C11B	118.1 (5)
N3A—C6A—C7A	119.2 (4)	C6B—C11B—C10B	119.5 (5)
C7A—C6A—C11A	120.9 (4)	C3B—C4B—H4B1	109.00
C6A—C7A—C8A	120.1 (4)	C3B—C4B—H4B2	109.00
C7A—C8A—C9A	118.0 (4)	C3B—C4B—H4B3	109.00
C8A—C9A—C10A	122.4 (4)	H4B1—C4B—H4B2	109.00
N4A—C9A—C8A	118.9 (4)	H4B1—C4B—H4B3	110.00
N4A—C9A—C10A	118.7 (4)	H4B2—C4B—H4B3	110.00
C9A—C10A—C11A	119.0 (4)	C1B—C5B—H5B1	109.00
C6A—C11A—C10A	119.6 (4)	C1B—C5B—H5B2	109.00
C3A—C4A—H4A1	109.00	C1B—C5B—H5B3	109.00
C3A—C4A—H4A2	109.00	H5B1—C5B—H5B2	110.00
H4A1—C4A—H4A2	110.00	H5B1—C5B—H5B3	109.00
H4A1—C4A—H4A3	109.00	H5B2—C5B—H5B3	109.00
C3A—C4A—H4A3	109.00	C6B—C7B—H7B	120.00
H4A2—C4A—H4A3	109.00	C8B—C7B—H7B	120.00
C1A—C5A—H5A1	109.00	C7B—C8B—H8B	121.00
C1A—C5A—H5A2	109.00	C9B—C8B—H8B	121.00
C1A—C5A—H5A3	109.00	C9B—C10B—H10B	121.00
H5A1—C5A—H5A2	109.00	C11B—C10B—H10B	121.00
H5A1—C5A—H5A3	110.00	C6B—C11B—H11B	120.00
H5A2—C5A—H5A3	110.00	C10B—C11B—H11B	120.00
C2A—N1A—N2A—N3A	−0.3 (5)	N3A—C1A—C2A—C3A	−177.7 (5)
N2A—N1A—C2A—C1A	0.3 (5)	C5A—C1A—C2A—C3A	−3.4 (8)
N2A—N1A—C2A—C3A	178.0 (4)	C5A—C1A—C2A—N1A	174.2 (5)
N1A—N2A—N3A—C1A	0.2 (5)	C1A—C2A—C3A—O1A	−14.0 (8)
N1A—N2A—N3A—C6A	−180.0 (4)	C1A—C2A—C3A—C4A	164.8 (5)
N2A—N3A—C1A—C2A	0.0 (5)	N1A—C2A—C3A—C4A	−12.5 (7)
N2A—N3A—C1A—C5A	−174.7 (4)	N1A—C2A—C3A—O1A	168.8 (5)
C6A—N3A—C1A—C2A	−179.9 (4)	N3A—C6A—C11A—C10A	179.1 (4)
C6A—N3A—C1A—C5A	5.4 (7)	N3A—C6A—C7A—C8A	−178.3 (4)
N2A—N3A—C6A—C7A	37.8 (6)	C11A—C6A—C7A—C8A	0.1 (7)
N2A—N3A—C6A—C11A	−140.7 (4)	C7A—C6A—C11A—C10A	0.6 (7)
C1A—N3A—C6A—C7A	−142.4 (5)	C6A—C7A—C8A—C9A	−0.6 (7)
C1A—N3A—C6A—C11A	39.1 (7)	C7A—C8A—C9A—C10A	0.3 (8)
O2A—N4A—C9A—C8A	−171.7 (5)	C7A—C8A—C9A—N4A	−179.5 (5)
O2A—N4A—C9A—C10A	8.5 (8)	N4A—C9A—C10A—C11A	−179.7 (4)
O3A—N4A—C9A—C8A	8.2 (8)	C8A—C9A—C10A—C11A	0.4 (8)
O3A—N4A—C9A—C10A	−171.7 (6)	C9A—C10A—C11A—C6A	−0.9 (7)
C2B—N1B—N2B—N3B	−0.7 (5)	N3B—C1B—C2B—N1B	−0.9 (5)
N2B—N1B—C2B—C1B	1.1 (6)	N3B—C1B—C2B—C3B	−177.2 (4)
N2B—N1B—C2B—C3B	177.6 (4)	C5B—C1B—C2B—N1B	177.0 (5)
N1B—N2B—N3B—C6B	−175.6 (4)	C5B—C1B—C2B—C3B	0.7 (9)
N1B—N2B—N3B—C1B	0.2 (5)	N1B—C2B—C3B—O1B	166.6 (5)
N2B—N3B—C1B—C2B	0.5 (5)	N1B—C2B—C3B—C4B	−12.9 (7)
N2B—N3B—C1B—C5B	−177.6 (5)	C1B—C2B—C3B—O1B	−17.6 (8)
C1B—N3B—C6B—C11B	−90.7 (6)	C1B—C2B—C3B—C4B	162.9 (5)
C6B—N3B—C1B—C5B	−2.3 (7)	N3B—C6B—C7B—C8B	179.6 (4)
N2B—N3B—C6B—C7B	−94.0 (5)	C11B—C6B—C7B—C8B	1.1 (8)
C6B—N3B—C1B—C2B	175.9 (4)	N3B—C6B—C11B—C10B	−179.5 (5)
C1B—N3B—C6B—C7B	90.9 (6)	C7B—C6B—C11B—C10B	−1.1 (8)
N2B—N3B—C6B—C11B	84.5 (5)	C6B—C7B—C8B—C9B	0.3 (8)
O3B—N4B—C9B—C8B	4.5 (7)	C7B—C8B—C9B—N4B	179.4 (5)
O2B—N4B—C9B—C10B	8.1 (7)	C7B—C8B—C9B—C10B	−1.8 (8)
O2B—N4B—C9B—C8B	−173.1 (5)	N4B—C9B—C10B—C11B	−179.4 (5)
O3B—N4B—C9B—C10B	−174.3 (5)	C8B—C9B—C10B—C11B	1.9 (8)
N3A—C1A—C2A—N1A	−0.2 (5)	C9B—C10B—C11B—C6B	−0.4 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C5B—H5B1···O3Ai	0.96	2.51	3.306 (8)	141
C10B—H10B···O1A	0.93	2.58	3.197 (7)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5B—H5B1⋯O3A i	0.96	2.51	3.306 (8)	141
C10B—H10B⋯O1A	0.93	2.58	3.197 (7)	124

Symmetry code: (i) .