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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 70| Part 3| March 2014| Pages o283-o284
doi:10.1107/S1600536814002037

1-Piperonylpiperazinium 4-chloro­benzoate

Channappa N. Kavitha,a Manpreet Kaur,a Brian J. Anderson,b Jerry P. Jasinskib* and H. S. Yathirajana

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
*Correspondence e-mail: jjasinski@keene.edu

(Received 20 January 2014; accepted 28 January 2014; online 12 February 2014)

In the title salt {systematic name: 1-[(1,3-benzodioxol-5-yl)meth­yl]piperazin-1-ium 4-chloro­benzoate}, C12H17N2O2+·C7H4ClO2−, the piperazine ring adopts a slightly disordered chair conformation. The dioxole ring is in a flattened envelope conformation with the methyl­ene C atom forming the flap. The relative orientation of the piperonyl ring system and the piperazine rings is reflected in the N—C—C C torsion angle of 132.3 (1)°. In the anion, the mean plane of the carboxyl­ate group is twisted from that of the benzene ring by 14.8 (9)°. In the crystal, the components are linked by N—H⋯O and weak C—H⋯O hydrogen bonds, forming chains along [010].

CCDC reference: 984052

Related literature

For the biological activity of related compounds, see: Brockunier et al. (2004[Brockunier, L. L., He, J., Colwell, L. F. Jr, Habulihaz, B., He, H., Leiting, B., Lyons, K. A., Marsilio, F., Patel, R. A., Teffera, Y., Wu, J. K., Thornberry, N. A., Weber, A. E. & Parmee, E. R. (2004). Bioorg. Med. Chem. Lett. 14, 4763-4766.]); Bogatcheva et al. (2006[Bogatcheva, E., Hanrahan, C., Nikonenko, B., Samala, R., Chen, P., Gearhart, J., Barbosa, F., Einck, L., Nacy, C. A. & Protopopova, M. (2006). J. Med. Chem. 49, 3045-3048.]); Elliott (2011[Elliott, S. (2011). Drug Test Anal. 3, 430-438.]); Gilbert et al. (1968[Gilbert, R., Canevari, R. J. M. J., Laubie, M. J. & Le Douarec, J. C. (1968). J. Med. Chem. 11, 1151-1155.]); Gobert et al. (2003[Gobert, A., Di Cara, B., Cistarelli, L. & Millan, M. J. (2003). J. Pharmacol. Exp. Ther. 305, 338-46.]); Millan et al. (2001[Millan, M. J., Cussac, D. & Milligan, G. (2001). J. Pharmacol. Exp. Ther. 297, 876-887.]). For a related structure, see: Capuano et al. (2000[Capuano, B., Crosby, I. T., Gable, R. W. & Lloyd, E. J. (2000). Acta Cryst. C56, 339-340.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C12H17N2O2+·C7H4ClO2−

  • Mr = 376.83

  • Monoclinic, P 21 /c

  • a = 16.9967 (6) Å

  • b = 8.5990 (3) Å

  • c = 12.4150 (5) Å

  • β = 90.923 (3)°

  • V = 1814.27 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 173 K

  • 0.48 × 0.26 × 0.18 mm
Data collection

  • Agilent Gemini EOS diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.787, Tmax = 1.000

  • 22917 measured reflections

  • 6302 independent reflections

  • 4472 reflections with I > 2σ(I)

  • Rint = 0.033
Refinement

  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.120

  • S = 1.04

  • 6302 reflections

  • 235 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2A—H2AA⋯O1Bi 0.90 1.87 2.7606 (15) 171
N2A—H2AB⋯O2Bii 0.90 1.78 2.6684 (16) 169
C10A—H10A⋯O2Biii 0.97 2.57 3.1974 (17) 122
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) -x+1, -y+2, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) in OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Supporting information

CCDC reference: 984052

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814002037/lh5687sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814002037/lh5687Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814002037/lh5687Isup3.cml

checkCIF report


Comment top

1-(3,4-Methylenedioxybenzyl)piperazine or 1-piperonylpiperazine is a psychoactive drug of the piperazine class and is used to synthesise the drug, piribedil, an antiparkinsonian agent (Millan et al., 2001). Piperonylpiperazine derivatives also have α-adrenergic antagonist properties (Gobert et al., 2003) and peripheral vasodilator properties (Gilbert et al., 1968). Piperazines are among the most important building blocks in today's drug discovery and are found in biologically active compounds across a number of different therapeutic areas (Brockunier et al., 2004; Bogatcheva et al., 2006). A review of the current pharmacological and toxicological information for piperazine derivatives is described (Elliott, 2011). The crystal structure of an N-piperonyl analogue of the atypical antipsychotic clozapine (Capuano et al., 2000) is reported. In continuation of our work on salts of piperonylpiperazines, this paper reports the crystal structure of the title compound (I).

The asymmetric unit of (I) consists of a 1-piperonylpiperazinium cation and a p-chlorobenzoate anion (Fig. 1). The piperazine ring in the cation adopts a slightly disordered chair conformation (puckering parameters Q, θ, and φ = 0.5761 (14) Å , 177.7 (2) ° and 177 (4) °; (Cremer & Pople, 1975). The dioxole group is in a slightly distorted envelope configuration (puckering parameters Q and φ = 0.1693 (15) Å and 36.1 (5) ° with atom C5A displaced by 0.2683 (18) Å from the plane through the other four atoms). The piperonyl ring system and the piperazine rings are twisted with respect to each other as reflected in the N1A-C1A-C2A-C8A torsion angle of 132.2 (5)°. In the anion, the mean plane of the carboxylate group is twisted from that of the benzene ring by 14.8 (9)°. Bond lengths are in normal ranges (Allen et al., 1987). In the crystal, N—H···O hydrogen bonds and a weak C10A—H10A···O2Biii intermolecular interactions are observed which influence the crystal packing stability forming 1-D chains along [0 1 0] (Fig. 2).

Related literature top

For the biological activity of related compounds, see: Brockunier et al. (2004); Bogatcheva et al. (2006); Elliott (2011); Gilbert et al. (1968); Gobert et al. (2003); Millan et al. (2001). For a related structure, see: Capuano et al. (2000). For puckering parameters, see: Cremer & Pople (1975). For standard bond lengths, see: Allen et al. (1987).

Experimental top

1-piperonylpiperazine ( 2.2 g, 0.01 mol) and p-chlorobenzoic acid (1.56 g, 0.01 mol) were dissolved in hot N,N-dimethylformamide and stirred for 10 mins at 323 K. The resulting solution was allowed to cool slowly at room temperature. The crystals of the title salt appeared after a few days and were suitable for X-ray studies (m.p.:464-470 K).

Refinement top

All H atoms were placed in calculated positions and then refined using the riding-model approximation with Atom—H lengths of 0.93Å (CH), 0.97Å (CH2) or 0.90Å (NH). Isotropic displacement parameters were set to 1.2Ueq of the parent atom.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) in OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I) with 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Crystal packing of (I) viewed along the c axis. Dashed lines indicate N—H···O and weak C—H···O interactions forming infinite 1-D chains along the b axis. H atoms not involved in hydrogen bonding have been removed for clarity.
1-[(1,3-Benzodioxol-5-yl)methyl]piperazin-1-ium 4-chlorobenzoate top
Crystal data top
C12H17N2O2+·C7H4ClO2−F(000) = 792
Mr = 376.83Dx = 1.380 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.9967 (6) ÅCell parameters from 5056 reflections
b = 8.5990 (3) Åθ = 3.1–32.8°
c = 12.4150 (5) ŵ = 0.24 mm−1
β = 90.923 (3)°T = 173 K
V = 1814.27 (12) Å3Irregular, light yellow
Z = 40.48 × 0.26 × 0.18 mm
Data collection top
Agilent Gemini EOS
diffractometer		6302 independent reflections
Radiation source: Enhance (Mo) X-ray Source4472 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1Rint = 0.033
ω scansθmax = 32.8°, θmin = 3.1°
Absorption correction: multi-scan
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)		h = −21→25
Tmin = 0.787, Tmax = 1.000k = −12→12
22917 measured reflectionsl = −17→18
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.120 w = 1/[σ2(Fo2) + (0.0455P)2 + 0.5274P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
6302 reflectionsΔρmax = 0.30 e Å−3
235 parametersΔρmin = −0.32 e Å−3
0 restraints
Crystal data top
C12H17N2O2+·C7H4ClO2−V = 1814.27 (12) Å3
Mr = 376.83Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.9967 (6) ŵ = 0.24 mm−1
b = 8.5990 (3) ÅT = 173 K
c = 12.4150 (5) Å0.48 × 0.26 × 0.18 mm
β = 90.923 (3)°
Data collection top
Agilent Gemini EOS
diffractometer		6302 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)		4472 reflections with I > 2σ(I)
Tmin = 0.787, Tmax = 1.000Rint = 0.033
22917 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.120H-atom parameters constrained
S = 1.04Δρmax = 0.30 e Å−3
6302 reflectionsΔρmin = −0.32 e Å−3
235 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.46343 (6)0.65641 (14)0.06488 (9)0.0439 (3)
O2A0.55838 (7)0.84302 (13)0.03707 (9)0.0452 (3)
N1A0.79257 (6)0.70236 (13)0.30762 (9)0.0280 (2)
N2A0.95243 (6)0.60800 (13)0.27472 (10)0.0298 (2)
H2AA0.95900.52930.32180.036*
H2AB0.99780.62090.23950.036*
C1A0.71612 (8)0.69075 (19)0.35969 (12)0.0360 (3)
H1AA0.70720.78430.40140.043*
H1AB0.71700.60330.40900.043*
C2A0.64927 (8)0.66996 (16)0.27979 (11)0.0301 (3)
C3A0.64318 (8)0.77080 (16)0.19132 (11)0.0321 (3)
H3A0.68100.84660.17890.039*
C4A0.57955 (8)0.75298 (16)0.12438 (11)0.0304 (3)
C5A0.49379 (11)0.7623 (2)−0.01222 (14)0.0474 (4)
H5AA0.45330.8355−0.03460.057*
H5AB0.51130.7063−0.07530.057*
C6A0.52267 (8)0.64112 (17)0.14120 (11)0.0312 (3)
C7A0.52767 (9)0.54095 (18)0.22546 (12)0.0373 (3)
H7A0.48950.46540.23670.045*
C8A0.59275 (9)0.55669 (18)0.29434 (12)0.0352 (3)
H8A0.59830.48850.35210.042*
C9A0.85456 (8)0.73757 (16)0.38737 (11)0.0305 (3)
H9AA0.85700.65530.44080.037*
H9AB0.84220.83400.42390.037*
C10A0.93326 (8)0.75244 (15)0.33388 (12)0.0313 (3)
H10A0.93200.83950.28420.038*
H10B0.97380.77270.38800.038*
C11A0.88861 (8)0.56853 (18)0.19658 (12)0.0349 (3)
H11A0.90030.47010.16210.042*
H11B0.88540.64790.14120.042*
C12A0.81076 (8)0.55708 (16)0.25287 (12)0.0316 (3)
H12A0.76950.53360.20050.038*
H12B0.81290.47300.30490.038*
Cl1B0.33436 (2)0.68123 (5)0.27279 (3)0.04524 (12)
O1B0.02434 (6)0.65334 (11)0.59960 (8)0.0335 (2)
O2B0.07906 (6)0.87721 (13)0.65085 (9)0.0411 (3)
C1B0.14214 (7)0.73384 (14)0.51518 (10)0.0255 (2)
C2B0.21013 (8)0.82354 (16)0.52310 (12)0.0308 (3)
H2B0.21520.89660.57800.037*
C3B0.27034 (8)0.80532 (16)0.45013 (12)0.0339 (3)
H3B0.31610.86420.45620.041*
C4B0.26105 (8)0.69800 (16)0.36822 (11)0.0310 (3)
C5B0.19465 (8)0.60586 (16)0.35906 (11)0.0311 (3)
H5B0.18970.53330.30380.037*
C6B0.13543 (8)0.62363 (15)0.43395 (11)0.0284 (3)
H6B0.09090.56100.42960.034*
C7B0.07682 (8)0.75601 (15)0.59450 (11)0.0275 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0290 (5)0.0598 (7)0.0426 (6)−0.0056 (5)−0.0065 (4)0.0000 (5)
O2A0.0446 (6)0.0445 (6)0.0461 (6)−0.0058 (5)−0.0140 (5)0.0112 (5)
N1A0.0247 (5)0.0295 (5)0.0297 (6)0.0009 (4)−0.0029 (4)−0.0040 (4)
N2A0.0248 (5)0.0248 (5)0.0398 (6)0.0004 (4)−0.0013 (4)0.0035 (5)
C1A0.0289 (7)0.0482 (9)0.0310 (7)0.0017 (6)0.0001 (5)−0.0022 (6)
C2A0.0243 (6)0.0350 (7)0.0311 (6)0.0031 (5)0.0028 (5)−0.0031 (5)
C3A0.0278 (6)0.0295 (7)0.0391 (7)−0.0028 (5)0.0005 (5)−0.0004 (5)
C4A0.0292 (6)0.0292 (6)0.0328 (7)0.0029 (5)0.0012 (5)−0.0007 (5)
C5A0.0497 (10)0.0517 (10)0.0403 (8)−0.0057 (8)−0.0118 (7)−0.0001 (7)
C6A0.0226 (6)0.0374 (7)0.0337 (7)0.0002 (5)0.0022 (5)−0.0067 (6)
C7A0.0312 (7)0.0422 (8)0.0387 (8)−0.0097 (6)0.0072 (6)−0.0005 (6)
C8A0.0341 (7)0.0399 (8)0.0317 (7)−0.0015 (6)0.0058 (5)0.0035 (6)
C9A0.0309 (7)0.0293 (6)0.0310 (6)0.0010 (5)−0.0055 (5)−0.0025 (5)
C10A0.0287 (6)0.0239 (6)0.0411 (7)−0.0019 (5)−0.0072 (5)−0.0013 (5)
C11A0.0304 (7)0.0355 (7)0.0385 (7)0.0033 (5)−0.0030 (6)−0.0084 (6)
C12A0.0276 (6)0.0276 (6)0.0393 (7)−0.0002 (5)−0.0049 (5)−0.0056 (5)
Cl1B0.0359 (2)0.0490 (2)0.0512 (2)−0.00034 (16)0.01216 (16)0.00508 (18)
O1B0.0296 (5)0.0288 (5)0.0421 (6)−0.0036 (4)0.0024 (4)0.0014 (4)
O2B0.0365 (6)0.0362 (5)0.0509 (6)−0.0063 (4)0.0073 (5)−0.0127 (5)
C1B0.0249 (6)0.0224 (6)0.0289 (6)0.0012 (4)−0.0045 (5)0.0052 (5)
C2B0.0282 (6)0.0271 (6)0.0369 (7)−0.0019 (5)−0.0059 (5)−0.0003 (5)
C3B0.0250 (6)0.0303 (7)0.0463 (8)−0.0035 (5)−0.0036 (5)0.0042 (6)
C4B0.0248 (6)0.0321 (7)0.0362 (7)0.0033 (5)0.0005 (5)0.0084 (5)
C5B0.0299 (6)0.0313 (7)0.0322 (7)0.0020 (5)−0.0043 (5)−0.0003 (5)
C6B0.0240 (6)0.0281 (6)0.0330 (7)−0.0018 (5)−0.0052 (5)0.0030 (5)
C7B0.0261 (6)0.0253 (6)0.0309 (6)0.0024 (5)−0.0046 (5)0.0031 (5)
Geometric parameters (Å, º) top
O1A—C5A1.424 (2)C9A—H9AA0.9700
O1A—C6A1.3777 (17)C9A—H9AB0.9700
O2A—C4A1.3753 (17)C9A—C10A1.508 (2)
O2A—C5A1.4281 (19)C10A—H10A0.9700
N1A—C1A1.4640 (17)C10A—H10B0.9700
N1A—C9A1.4658 (16)C11A—H11A0.9700
N1A—C12A1.4578 (17)C11A—H11B0.9700
N2A—H2AA0.9000C11A—C12A1.510 (2)
N2A—H2AB0.9000C12A—H12A0.9700
N2A—C10A1.4818 (17)C12A—H12B0.9700
N2A—C11A1.4829 (18)Cl1B—C4B1.7391 (14)
C1A—H1AA0.9700O1B—C7B1.2573 (16)
C1A—H1AB0.9700O2B—C7B1.2554 (16)
C1A—C2A1.5069 (19)C1B—C2B1.3916 (18)
C2A—C3A1.4019 (19)C1B—C6B1.3873 (18)
C2A—C8A1.382 (2)C1B—C7B1.5079 (18)
C3A—H3A0.9300C2B—H2B0.9300
C3A—C4A1.3619 (19)C2B—C3B1.386 (2)
C4A—C6A1.3820 (19)C3B—H3B0.9300
C5A—H5AA0.9700C3B—C4B1.380 (2)
C5A—H5AB0.9700C4B—C5B1.382 (2)
C6A—C7A1.357 (2)C5B—H5B0.9300
C7A—H7A0.9300C5B—C6B1.3896 (19)
C7A—C8A1.394 (2)C6B—H6B0.9300
C8A—H8A0.9300
C6A—O1A—C5A104.75 (11)N1A—C9A—C10A110.67 (11)
C4A—O2A—C5A104.70 (12)H9AA—C9A—H9AB108.1
C1A—N1A—C9A110.44 (11)C10A—C9A—H9AA109.5
C12A—N1A—C1A110.11 (11)C10A—C9A—H9AB109.5
C12A—N1A—C9A109.66 (10)N2A—C10A—C9A110.53 (11)
H2AA—N2A—H2AB108.1N2A—C10A—H10A109.5
C10A—N2A—H2AA109.5N2A—C10A—H10B109.5
C10A—N2A—H2AB109.5C9A—C10A—H10A109.5
C10A—N2A—C11A110.60 (10)C9A—C10A—H10B109.5
C11A—N2A—H2AA109.5H10A—C10A—H10B108.1
C11A—N2A—H2AB109.5N2A—C11A—H11A109.6
N1A—C1A—H1AA109.1N2A—C11A—H11B109.6
N1A—C1A—H1AB109.1N2A—C11A—C12A110.45 (12)
N1A—C1A—C2A112.49 (11)H11A—C11A—H11B108.1
H1AA—C1A—H1AB107.8C12A—C11A—H11A109.6
C2A—C1A—H1AA109.1C12A—C11A—H11B109.6
C2A—C1A—H1AB109.1N1A—C12A—C11A110.74 (11)
C3A—C2A—C1A119.20 (13)N1A—C12A—H12A109.5
C8A—C2A—C1A121.06 (13)N1A—C12A—H12B109.5
C8A—C2A—C3A119.71 (13)C11A—C12A—H12A109.5
C2A—C3A—H3A121.4C11A—C12A—H12B109.5
C4A—C3A—C2A117.16 (13)H12A—C12A—H12B108.1
C4A—C3A—H3A121.4C2B—C1B—C7B120.21 (12)
O2A—C4A—C6A109.64 (12)C6B—C1B—C2B119.24 (12)
C3A—C4A—O2A127.79 (13)C6B—C1B—C7B120.56 (11)
C3A—C4A—C6A122.46 (13)C1B—C2B—H2B119.6
O1A—C5A—O2A107.89 (12)C3B—C2B—C1B120.80 (13)
O1A—C5A—H5AA110.1C3B—C2B—H2B119.6
O1A—C5A—H5AB110.1C2B—C3B—H3B120.7
O2A—C5A—H5AA110.1C4B—C3B—C2B118.69 (13)
O2A—C5A—H5AB110.1C4B—C3B—H3B120.7
H5AA—C5A—H5AB108.4C3B—C4B—Cl1B118.85 (11)
O1A—C6A—C4A109.57 (13)C3B—C4B—C5B121.83 (13)
C7A—C6A—O1A128.82 (13)C5B—C4B—Cl1B119.31 (11)
C7A—C6A—C4A121.54 (13)C4B—C5B—H5B120.6
C6A—C7A—H7A121.6C4B—C5B—C6B118.77 (13)
C6A—C7A—C8A116.78 (13)C6B—C5B—H5B120.6
C8A—C7A—H7A121.6C1B—C6B—C5B120.64 (12)
C2A—C8A—C7A122.33 (14)C1B—C6B—H6B119.7
C2A—C8A—H8A118.8C5B—C6B—H6B119.7
C7A—C8A—H8A118.8O1B—C7B—C1B118.33 (12)
N1A—C9A—H9AA109.5O2B—C7B—O1B124.75 (13)
N1A—C9A—H9AB109.5O2B—C7B—C1B116.92 (12)
O1A—C6A—C7A—C8A−176.43 (14)C6A—C7A—C8A—C2A1.1 (2)
O2A—C4A—C6A—O1A0.07 (16)C8A—C2A—C3A—C4A1.3 (2)
O2A—C4A—C6A—C7A−177.15 (13)C9A—N1A—C1A—C2A174.49 (12)
N1A—C1A—C2A—C3A−49.87 (18)C9A—N1A—C12A—C11A−59.59 (14)
N1A—C1A—C2A—C8A132.26 (14)C10A—N2A—C11A—C12A−55.32 (15)
N1A—C9A—C10A—N2A−57.53 (14)C11A—N2A—C10A—C9A55.29 (14)
N2A—C11A—C12A—N1A57.83 (15)C12A—N1A—C1A—C2A−64.26 (15)
C1A—N1A—C9A—C10A−179.02 (11)C12A—N1A—C9A—C10A59.46 (14)
C1A—N1A—C12A—C11A178.69 (11)Cl1B—C4B—C5B—C6B−178.09 (10)
C1A—C2A—C3A—C4A−176.59 (13)C1B—C2B—C3B—C4B1.0 (2)
C1A—C2A—C8A—C7A175.95 (13)C2B—C1B—C6B—C5B−2.03 (19)
C2A—C3A—C4A—O2A175.68 (13)C2B—C1B—C7B—O1B−165.32 (12)
C2A—C3A—C4A—C6A0.0 (2)C2B—C1B—C7B—O2B14.80 (18)
C3A—C2A—C8A—C7A−1.9 (2)C2B—C3B—C4B—Cl1B177.00 (10)
C3A—C4A—C6A—O1A176.46 (13)C2B—C3B—C4B—C5B−1.9 (2)
C3A—C4A—C6A—C7A−0.8 (2)C3B—C4B—C5B—C6B0.8 (2)
C4A—O2A—C5A—O1A18.16 (18)C4B—C5B—C6B—C1B1.22 (19)
C4A—C6A—C7A—C8A0.2 (2)C6B—C1B—C2B—C3B0.89 (19)
C5A—O1A—C6A—C4A11.18 (16)C6B—C1B—C7B—O1B14.36 (18)
C5A—O1A—C6A—C7A−171.86 (16)C6B—C1B—C7B—O2B−165.52 (12)
C5A—O2A—C4A—C3A172.60 (15)C7B—C1B—C2B—C3B−179.42 (12)
C5A—O2A—C4A—C6A−11.25 (16)C7B—C1B—C6B—C5B178.29 (11)
C6A—O1A—C5A—O2A−18.11 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2AA···O1Bi0.901.872.7606 (15)171
N2A—H2AB···O2Bii0.901.782.6684 (16)169
C10A—H10A···O2Biii0.972.573.1974 (17)122
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, −y+3/2, z−1/2; (iii) −x+1, −y+2, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2AA···O1Bi0.901.872.7606 (15)170.9
N2A—H2AB···O2Bii0.901.782.6684 (16)168.9
C10A—H10A···O2Biii0.972.573.1974 (17)122.2
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, −y+3/2, z−1/2; (iii) −x+1, −y+2, −z+1.
 

Acknowledgements

CNK thanks the University of Mysore for research facilities and is also grateful to the Principal, Maharani's Science College for Women, Mysore, for giving permission to undertake research. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

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ISSN: 2056-9890
Volume 70| Part 3| March 2014| Pages o283-o284
doi:10.1107/S1600536814002037
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