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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 1| January 2015| Pages o17-o18
https://doi.org/10.1107/S2056989014026127

Crystal structure of 2-aza­niumyl-3-bromo-6-oxo-5,6-di­hydro­pyrido[1,2-a]quinoxalin-11-ium dibromide

Md. Serajul Haque Faizi,a Natalia O. Sharkinab* and Turganbay S. Iskenderovb

aDepartment of Chemistry, Indian Institute of Technology Kanpur, Kanpur, UP 208 016, India, and bNational Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv, Ukraine
*Correspondence e-mail: nsharkina@ukr.net

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 2 November 2014; accepted 27 November 2014; online 1 January 2015)

The title salt, C12H10BrN3O2+·2Br−, was synthesized from the reaction of N1,N4-bis­(pyridin-2-yl­methyl­idene)benzene-1,4-di­amine and bromine in a methanol solution. All non-H atoms of the 2-aza­niumyl-3-bromo-6-oxo-5,6-di­hydro­pyrido[1,2-a]quinoxalin-11-ium cation are nearly coplanar, the maximum deviation being 0.114 (4) Å. In the crystal, the cations and anions are linked through N—H⋯Br hydrogen bonds and weak C—H⋯Br inter­actions, forming a three-dimensional supra­molecular architecture. A short Br⋯Br contact [3.3088 (9) Å] is observed in the crystal.

CCDC reference: 1036569

Similar articles

1. Related literature

For applications of quinoxalines, see: Duffy et al. (2002[Duffy, K. J., Haltiwanger, R. C., Freyer, A. J., Li, F., Luengo, J. I. & Cheng, H.-Y. (2002). J. Chem. Soc. Perkin Trans. 2, pp. 181-185.]); Gazit et al. (1996[Gazit, A., App, H., McMahon, G., Chen, J., Levitzki, A. & Bohmer, F. D. (1996). J. Med. Chem. 39, 2170-2177.]); Harmenberg et al. (1991[Harmenberg, J., Åkesson-Johansson, A., Gräslund, A., Malmfors, T., Bergman, J., Wahren, B., Åkerfeldt, S., Lundblad, L. & Cox, S. (1991). Antiviral Res. 15, 193-204.]); Naylor et al. (1993[Naylor, M. A., Stephens, M. A., Nolan, J., Sutton, B., Tocher, J. H., Fielden, E. M., Adams, G. E. & Stratford, I. J. (1993). Anticancer Drug. Des. 8, 439-461.]). For types of quinoxalines and a structure similar to title compound, see: Eiden & Peter (1966[Eiden, F. & Peter, P. (1966). Arch. Pharm. Pharm. Med. Chem. 299, 139-146.]); Koner & Ray (2008[Koner, R. R. & Ray, M. (2008). Inorg. Chem. 47, 9122-9124.]); Fritsky et al. (2006[Fritsky, I. O., Kozłowski, H., Kanderal, O. M., Haukka, M., Świątek-Kozłowska, J., Gumienna-Kontecka, E. & Meyer, F. (2006). Chem. Commun. pp. 4125-4127.]); Kanderal et al. (2005[Kanderal, O. M., Kozlowski, H., Dobosz, A., Swiatek-Kozlowska, J., Meyer, F. & Fritsky, I. O. (2005). Dalton Trans. pp. 1428-1437.]); Moroz et al. (2012[Moroz, Y. S., Demeshko, S., Haukka, M., Mokhir, A., Mitra, U., Stocker, M., Müller, P., Meyer, F. & Fritsky, I. O. (2012). Inorg. Chem. 51, 7445-7447.]). For background to and applications of related compounds, see: Faizi & Sen (2014[Faizi, M. S. H. & Sen, P. (2014). Acta Cryst. E70, m206-m207.]); Faizi et al. (2014[Faizi, M. S. H., Mashrai, A., Shahid, M. & Ahmad, M. (2014). Acta Cryst. E70, o806.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C12H10BrN3O2+·2Br−

  • Mr = 451.96

  • Monoclinic, P 21 /c

  • a = 5.6782 (2) Å

  • b = 11.9822 (4) Å

  • c = 20.2528 (7) Å

  • β = 90.891 (2)°

  • V = 1377.78 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 8.78 mm−1

  • T = 100 K

  • 0.30 × 0.25 × 0.20 mm

2.2. Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.178, Tmax = 0.273

  • 14369 measured reflections

  • 2424 independent reflections

  • 1804 reflections with I > 2σ(I)

  • Rint = 0.106

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.130

  • S = 0.97

  • 2424 reflections

  • 173 parameters

  • H-atom parameters constrained

  • Δρmax = 1.23 e Å−3

  • Δρmin = −0.88 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2A⋯Br1i 0.88 2.46 3.322 (5) 167
N3—H1N3⋯Br2ii 0.91 2.53 3.432 (5) 171
N3—H2N3⋯Br2iii 0.91 2.42 3.287 (5) 160
N3—H3N3⋯Br1 0.91 2.50 3.374 (5) 162
C2—H2⋯Br2iv 0.95 2.91 3.813 (6) 160
C3—H3⋯Br1v 0.95 2.85 3.752 (7) 160
C8—H8⋯Br1i 0.95 2.86 3.672 (6) 144
C11—H11⋯Br2ii 0.95 2.80 3.639 (6) 148
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iv) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (v) [x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenberg & Putz, 2006[Brandenberg, K. & Putz, H. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: DIAMOND.

Supporting information

CCDC reference: 1036569

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989014026127/xu5829sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989014026127/xu5829Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989014026127/xu5829Isup3.cml

checkCIF report


Comment top

Quinoxalines are an important class of heterocyclic compounds, some of which are found to be useful as fluorophores, dyes, and antibiotics (Duffy et al., 2002; Gazit et al., 1996). Many drug candidates bearing quinoxaline core structures are in clinical trials in antiviral, anticancer and CNS (central nervous system) therapeutic areas (Harmenberg et al., 1991; Naylor et al., 1993). The present work is a part of an ongoing structural study of Schiff bases and their utilization in the synthesis of previously unknown organic and polynuclear coordination compounds (Faizi & Sen, 2014; Faizi et al., 2014; Moroz et al., 2012), and we report here synthesis and structure of 2-azaniumyl-3-bromo-6-oxo-5,6-dihydropyrido[1,2-a]quinoxalin-11-ium bromide (ABODQ). There are very few examples similar to title compound have been reported in the literature (Eiden & Peter, 1966).

The title compound was synthesized from the reaction of two equimolar amounts of molecular bromine and pyridine derivative Schiff base N1,N4-bis(pyridine-2-ylmethylene) benzene-1,4-diamine (BPYBD). The cyclization occurs by oxidation of BPYBD, reduction of molecular bromine and finally hydrolysis of the imine bond which creates the dication at two of the nitrogen atoms in the quinoxaline ring system.

In the structure of the title bromide salt, the dication is essentially planar with a longer C10—N3 distance of 1.45 (3) Å, compared to the usual Caro—Namine single bond distance of 1.43 (3) Å. This might be due to the electron withdrawing effect of positively charged pyridine, which increased the C-Namine bond order. Other C—C and C—N bond distances are well within the limits expected for aromatic rings (Koner & Ray, 2008; Kanderal et al., 2005; Fritsky et al., 2006).

The asymmetric unit contains a discrete 2-azaniumyl-3-bromo-6-oxo-5,6-dihydropyrido[1,2-a]quinoxalin-11-ium cation, with a protonated amine, pyridine group, and two bromide anion (Fig 1). In title compound, the ions are connected into a three dimensional hydrogen-bonded network via N—H···Br and C—H···Br hydrogen bonds (Table 1). All Hammonium atoms and Hpyrazine N—H group are involved in hydrogen bonds with two different bromide ions, and each anion accepts hydrogen bonds from three different cations. No intermolecular π–π interations are evident in the hydrocarbon layer in title compound.

Related literature top

For applications of quinoxalines, see: Duffy et al. (2002); Gazit et al. (1996); Harmenberg et al. (1991); Naylor et al. (1993). For types of quinoxalines and a structure similar to title compound, see: Eiden & Peter (1966); Koner & Ray (2008); Fritsky et al. (2006); Kanderal et al. (2005); Moroz et al. (2012). For background to and applications of related compounds, see: Faizi & Sen (2014); Faizi et al. (2014).

Experimental top

Molecular bromine (220 mg, 72.0 mL, 1.40 mmol) was added to a methanolic solution (10 ml) of Schiff base, N1,N4-bis (pyridine-2-ylmethylene)benzene-1,4-diamine (BPYBD) (197 mg, 0.70 mmol). The color of the solution was immediately changed from yellow to orange. The reaction mixture was stirred for 4 h at room temperature under hood. The resulting yellow precipitate was recovered by filtration, washed several times with a small portions of acetone and then with diethyl ether to give 200 mg (64%) of 2-azaniumyl-3-bromo-6-oxo-5,6-dihydropyrido [1,2-a]quinoxalin-11-ium bromide (ABODQ). The crystal of the title compound suitable for X-ray analysis was obtained within 3 days by slow evaporation of the methanol solvent.

Refinement top

H atoms were placed in calculated positions and treated as riding on their parent atoms with C—H = 0.95 Å, N—H = 0.88 or 0.91 Å. Uiso(H) = 1.5Ueq(N) for the amino-H atoms and 1.2Ueq(C,N) for the others.

Structure description top

Quinoxalines are an important class of heterocyclic compounds, some of which are found to be useful as fluorophores, dyes, and antibiotics (Duffy et al., 2002; Gazit et al., 1996). Many drug candidates bearing quinoxaline core structures are in clinical trials in antiviral, anticancer and CNS (central nervous system) therapeutic areas (Harmenberg et al., 1991; Naylor et al., 1993). The present work is a part of an ongoing structural study of Schiff bases and their utilization in the synthesis of previously unknown organic and polynuclear coordination compounds (Faizi & Sen, 2014; Faizi et al., 2014; Moroz et al., 2012), and we report here synthesis and structure of 2-azaniumyl-3-bromo-6-oxo-5,6-dihydropyrido[1,2-a]quinoxalin-11-ium bromide (ABODQ). There are very few examples similar to title compound have been reported in the literature (Eiden & Peter, 1966).

The title compound was synthesized from the reaction of two equimolar amounts of molecular bromine and pyridine derivative Schiff base N1,N4-bis(pyridine-2-ylmethylene) benzene-1,4-diamine (BPYBD). The cyclization occurs by oxidation of BPYBD, reduction of molecular bromine and finally hydrolysis of the imine bond which creates the dication at two of the nitrogen atoms in the quinoxaline ring system.

In the structure of the title bromide salt, the dication is essentially planar with a longer C10—N3 distance of 1.45 (3) Å, compared to the usual Caro—Namine single bond distance of 1.43 (3) Å. This might be due to the electron withdrawing effect of positively charged pyridine, which increased the C-Namine bond order. Other C—C and C—N bond distances are well within the limits expected for aromatic rings (Koner & Ray, 2008; Kanderal et al., 2005; Fritsky et al., 2006).

The asymmetric unit contains a discrete 2-azaniumyl-3-bromo-6-oxo-5,6-dihydropyrido[1,2-a]quinoxalin-11-ium cation, with a protonated amine, pyridine group, and two bromide anion (Fig 1). In title compound, the ions are connected into a three dimensional hydrogen-bonded network via N—H···Br and C—H···Br hydrogen bonds (Table 1). All Hammonium atoms and Hpyrazine N—H group are involved in hydrogen bonds with two different bromide ions, and each anion accepts hydrogen bonds from three different cations. No intermolecular π–π interations are evident in the hydrocarbon layer in title compound.

For applications of quinoxalines, see: Duffy et al. (2002); Gazit et al. (1996); Harmenberg et al. (1991); Naylor et al. (1993). For types of quinoxalines and a structure similar to title compound, see: Eiden & Peter (1966); Koner & Ray (2008); Fritsky et al. (2006); Kanderal et al. (2005); Moroz et al. (2012). For background to and applications of related compounds, see: Faizi & Sen (2014); Faizi et al. (2014).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenberg & Putz, 2006); software used to prepare material for publication: DIAMOND (Brandenberg & Putz, 2006).

Figures top
[Figure 1] Fig. 1. The molecular conformation and atom-numbering scheme for the title compound, with non-H atoms drawn as 40% probability displacement ellipsoids.
2-Azaniumyl-3-bromo-6-oxo-5,6-dihydropyrido[1,2-a]quinoxalin-11-ium dibromide top
Crystal data top
C12H10BrN3O2+·2Br−F(000) = 864
Mr = 451.96Dx = 2.179 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 999 reflections
a = 5.6782 (2) Åθ = 2.6–28.6°
b = 11.9822 (4) ŵ = 8.78 mm−1
c = 20.2528 (7) ÅT = 100 K
β = 90.891 (2)°Block, yellow
V = 1377.78 (8) Å30.30 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer		2424 independent reflections
Radiation source: fine-focus sealed tube1804 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.106
ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −6→6
Tmin = 0.178, Tmax = 0.273k = −14→14
14369 measured reflectionsl = −23→24
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0801P)2]
where P = (Fo2 + 2Fc2)/3
2424 reflections(Δ/σ)max < 0.001
173 parametersΔρmax = 1.23 e Å−3
0 restraintsΔρmin = −0.88 e Å−3
Crystal data top
C12H10BrN3O2+·2Br−V = 1377.78 (8) Å3
Mr = 451.96Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.6782 (2) ŵ = 8.78 mm−1
b = 11.9822 (4) ÅT = 100 K
c = 20.2528 (7) Å0.30 × 0.25 × 0.20 mm
β = 90.891 (2)°
Data collection top
Bruker SMART APEX CCD
diffractometer		2424 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		1804 reflections with I > 2σ(I)
Tmin = 0.178, Tmax = 0.273Rint = 0.106
14369 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.130H-atom parameters constrained
S = 0.97Δρmax = 1.23 e Å−3
2424 reflectionsΔρmin = −0.88 e Å−3
173 parameters
Special details top

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
xyzUiso*/Ueq
C11.1684 (11)0.3466 (5)0.6250 (3)0.0348 (16)
H11.18050.37790.58210.042*
C21.3279 (12)0.3771 (5)0.6724 (3)0.0404 (17)
H21.44790.42970.66280.049*
C31.3135 (12)0.3313 (6)0.7341 (3)0.0432 (18)
H31.42460.35110.76760.052*
C41.1375 (12)0.2564 (6)0.7472 (3)0.0408 (17)
H41.12930.22300.78960.049*
C50.9719 (11)0.2291 (5)0.6989 (3)0.0308 (15)
C60.7750 (11)0.1557 (5)0.7166 (3)0.0327 (15)
C70.6487 (11)0.1672 (5)0.6019 (3)0.0284 (14)
C80.4824 (11)0.1344 (5)0.5543 (3)0.0297 (14)
H80.35820.08510.56550.036*
C90.5012 (11)0.1750 (5)0.4905 (3)0.0287 (14)
C100.6803 (11)0.2482 (5)0.4745 (3)0.0272 (14)
C110.8407 (11)0.2812 (5)0.5212 (3)0.0294 (14)
H110.96190.33230.51040.035*
C120.8249 (11)0.2387 (5)0.5857 (3)0.0252 (14)
N10.9939 (8)0.2736 (4)0.6368 (2)0.0262 (11)
N20.6287 (9)0.1254 (4)0.6658 (2)0.0319 (12)
H2A0.51600.07700.67370.038*
N30.6987 (9)0.2912 (4)0.4080 (2)0.0343 (13)
H1N30.82780.33600.40540.052*
H2N30.56730.33140.39760.052*
H3N30.71260.23340.37920.052*
O10.7430 (8)0.1251 (4)0.7735 (2)0.0428 (12)
Br10.82448 (12)0.04974 (5)0.33038 (3)0.0399 (2)
Br20.21399 (13)0.05913 (6)0.91141 (4)0.0478 (3)
Br30.26693 (12)0.12868 (6)0.42784 (3)0.0388 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.035 (4)0.036 (4)0.033 (4)−0.004 (3)0.000 (3)0.003 (3)
C20.038 (4)0.036 (4)0.047 (4)−0.002 (3)−0.002 (3)−0.002 (3)
C30.038 (5)0.053 (5)0.038 (4)0.003 (4)−0.005 (3)−0.015 (4)
C40.039 (4)0.053 (4)0.030 (4)0.001 (3)−0.002 (3)−0.007 (3)
C50.031 (4)0.040 (4)0.021 (3)0.004 (3)0.002 (3)−0.005 (3)
C60.030 (4)0.040 (4)0.028 (4)0.006 (3)−0.002 (3)−0.008 (3)
C70.036 (4)0.031 (4)0.018 (3)0.002 (3)0.002 (3)−0.001 (3)
C80.026 (4)0.031 (3)0.032 (4)0.001 (3)0.004 (3)0.000 (3)
C90.029 (4)0.033 (3)0.024 (3)0.004 (3)−0.008 (3)−0.005 (3)
C100.030 (4)0.035 (4)0.016 (3)0.005 (3)0.006 (2)−0.002 (3)
C110.023 (4)0.035 (4)0.030 (3)−0.002 (3)0.007 (3)−0.002 (3)
C120.026 (4)0.027 (3)0.022 (3)0.000 (3)0.003 (3)−0.002 (3)
N10.026 (3)0.030 (3)0.023 (3)0.001 (2)0.001 (2)−0.002 (2)
N20.033 (3)0.037 (3)0.026 (3)−0.002 (2)0.005 (2)0.002 (2)
N30.041 (4)0.043 (3)0.020 (3)0.005 (2)0.004 (2)0.002 (2)
O10.050 (3)0.062 (3)0.016 (2)−0.007 (2)0.008 (2)0.004 (2)
Br10.0317 (5)0.0464 (5)0.0415 (4)−0.0044 (3)0.0032 (3)−0.0017 (3)
Br20.0423 (5)0.0435 (5)0.0579 (5)−0.0028 (3)0.0115 (4)−0.0072 (3)
Br30.0370 (5)0.0460 (5)0.0333 (4)0.0011 (3)−0.0044 (3)−0.0048 (3)
Geometric parameters (Å, º) top
C1—N11.346 (7)C7—N21.394 (7)
C1—C21.359 (9)C8—C91.387 (8)
C1—H10.9500C8—H80.9500
C2—C31.368 (9)C9—C101.385 (9)
C2—H20.9500C9—Br31.907 (6)
C3—C41.372 (10)C10—C111.362 (8)
C3—H30.9500C10—N31.449 (7)
C4—C51.384 (8)C11—C121.405 (8)
C4—H40.9500C11—H110.9500
C5—N11.374 (7)C12—N11.462 (7)
C5—C61.471 (9)N2—H2A0.8800
C6—O11.225 (7)N3—H1N30.9100
C6—N21.361 (8)N3—H2N30.9100
C7—C121.361 (8)N3—H3N30.9100
C7—C81.395 (8)
N1—C1—C2122.3 (6)C8—C9—C10120.5 (6)
N1—C1—H1118.9C8—C9—Br3117.1 (5)
C2—C1—H1118.9C10—C9—Br3122.4 (4)
C1—C2—C3119.2 (7)C11—C10—C9120.5 (5)
C1—C2—H2120.4C11—C10—N3119.0 (6)
C3—C2—H2120.4C9—C10—N3120.5 (5)
C2—C3—C4119.6 (6)C10—C11—C12119.2 (6)
C2—C3—H3120.2C10—C11—H11120.4
C4—C3—H3120.2C12—C11—H11120.4
C3—C4—C5120.4 (6)C7—C12—C11120.7 (6)
C3—C4—H4119.8C7—C12—N1119.1 (5)
C5—C4—H4119.8C11—C12—N1120.2 (5)
N1—C5—C4119.0 (6)C1—N1—C5119.5 (5)
N1—C5—C6122.3 (5)C1—N1—C12122.5 (5)
C4—C5—C6118.7 (6)C5—N1—C12118.0 (5)
O1—C6—N2122.2 (6)C6—N2—C7123.2 (5)
O1—C6—C5122.1 (6)C6—N2—H2A118.4
N2—C6—C5115.7 (5)C7—N2—H2A118.4
C12—C7—C8120.2 (5)C10—N3—H1N3109.5
C12—C7—N2121.4 (5)C10—N3—H2N3109.5
C8—C7—N2118.5 (6)H1N3—N3—H2N3109.5
C9—C8—C7119.0 (6)C10—N3—H3N3109.5
C9—C8—H8120.5H1N3—N3—H3N3109.5
C7—C8—H8120.5H2N3—N3—H3N3109.5
N1—C1—C2—C30.9 (10)N2—C7—C12—C11−179.2 (5)
C1—C2—C3—C4−0.7 (11)C8—C7—C12—N1178.6 (5)
C2—C3—C4—C5−1.5 (11)N2—C7—C12—N1−1.1 (9)
C3—C4—C5—N13.4 (10)C10—C11—C12—C7−1.4 (9)
C3—C4—C5—C6−175.0 (6)C10—C11—C12—N1−179.5 (5)
N1—C5—C6—O1−172.7 (6)C2—C1—N1—C51.1 (9)
C4—C5—C6—O15.7 (9)C2—C1—N1—C12−178.7 (6)
N1—C5—C6—N26.4 (8)C4—C5—N1—C1−3.2 (9)
C4—C5—C6—N2−175.2 (6)C6—C5—N1—C1175.2 (5)
C12—C7—C8—C90.6 (9)C4—C5—N1—C12176.5 (5)
N2—C7—C8—C9−179.7 (5)C6—C5—N1—C12−5.1 (8)
C7—C8—C9—C10−0.9 (9)C7—C12—N1—C1−178.0 (6)
C7—C8—C9—Br3−179.4 (4)C11—C12—N1—C10.1 (9)
C8—C9—C10—C110.1 (9)C7—C12—N1—C52.3 (8)
Br3—C9—C10—C11178.4 (4)C11—C12—N1—C5−179.6 (5)
C8—C9—C10—N3−179.5 (5)O1—C6—N2—C7174.0 (6)
Br3—C9—C10—N3−1.1 (8)C5—C6—N2—C7−5.1 (8)
C9—C10—C11—C121.1 (9)C12—C7—N2—C62.7 (9)
N3—C10—C11—C12−179.3 (5)C8—C7—N2—C6−177.0 (5)
C8—C7—C12—C110.6 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···Br1i0.882.463.322 (5)167
N3—H1N3···Br2ii0.912.533.432 (5)171
N3—H2N3···Br2iii0.912.423.287 (5)160
N3—H3N3···Br10.912.503.374 (5)162
C2—H2···Br2iv0.952.913.813 (6)160
C3—H3···Br1v0.952.853.752 (7)160
C8—H8···Br1i0.952.863.672 (6)144
C11—H11···Br2ii0.952.803.639 (6)148
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, −y+1/2, z−1/2; (iii) x, −y+1/2, z−1/2; (iv) −x+2, y+1/2, −z+3/2; (v) x+1, −y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···Br1i0.882.463.322 (5)167
N3—H1N3···Br2ii0.912.533.432 (5)171
N3—H2N3···Br2iii0.912.423.287 (5)160
N3—H3N3···Br10.912.503.374 (5)162
C2—H2···Br2iv0.952.913.813 (6)160
C3—H3···Br1v0.952.853.752 (7)160
C8—H8···Br1i0.952.863.672 (6)144
C11—H11···Br2ii0.952.803.639 (6)148
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, −y+1/2, z−1/2; (iii) x, −y+1/2, z−1/2; (iv) −x+2, y+1/2, −z+3/2; (v) x+1, −y+1/2, z+1/2.
 

Acknowledgements

The authors are grateful to the Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, UP 208 016, India, for X-ray data collection.

References

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ISSN: 2056-9890
Volume 71| Part 1| January 2015| Pages o17-o18
https://doi.org/10.1107/S2056989014026127
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