3-Amino-1H-pyrazol-2-ium tri­fluoro­acetate

Yamuna, T.S.; Jasinski, J.P.; Scadova, D.R.; Yathirajan, H.S.; Kaur, M.

doi:10.1107/S1600536813022204

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 9| September 2013| Pages o1425-o1426

doi:10.1107/S1600536813022204

Open

access

3-Amino-1H-pyrazol-2-ium trifluoroacetate

T. S. Yamuna,^a Jerry P. Jasinski,^b ^* Derek R. Scadova,^b H. S. Yathirajan ^a and Manpreet Kaur ^a

^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 July 2013; accepted 7 August 2013; online 14 August 2013)

The asymmetric unit of the title salt, C₃H₆N₃⁺·C₂F₃O₂⁻, contains two independent 3-aminopyrazolium cations and two independent trifluoroacetate anions. The F atoms of both anions were refined as disordered over two sets of sites, with common occupancy ratios of 0.639 (12):0.361 (12). In the crystal, the cations and anions are linked via N—H⋯O hydrogen bonds, forming chains along [100] and [010].

Related literature

For biological properties of pyrazole derivatives, see: Hall et al. (2008 ); Isloor et al. (2009 ); Patel et al. (2010 ); Samshuddin et al. (2010 ). For the chemistry of aminopyrazoles, see: Giuseppe et al. (1991 ). For the medicinal activity of pyrazoles, see: Vinogradov et al. (1994 ). For related structures, see: Dobson & Gerkin (1998 ); Foces-Foces et al. (1996 ); Hemamalini & Fun (2010 ); Thanigaimani et al. (2012 ). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₃H₆N₃⁺·C₂F₃O₂⁻
M_r = 197.13
Monoclinic, P 2₁ /n
a = 10.9292 (8) Å
b = 10.9332 (6) Å
c = 13.7002 (13) Å
β = 107.939 (9)°
V = 1557.5 (2) Å³
Z = 8
Cu Kα radiation
μ = 1.58 mm⁻¹
T = 173 K
0.16 × 0.14 × 0.06 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ) T_min = 0.662, T_max = 1.000
9227 measured reflections
3031 independent reflections
2343 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.136
S = 1.05
3031 reflections
338 parameters
All H-atom parameters refined
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1AA⋯O1Aⁱ	0.85 (3)	2.28 (3)	2.936 (3)	134 (2)
N1A—H1AB⋯O2Aⁱⁱ	0.91 (3)	1.99 (3)	2.884 (3)	169 (3)
N2A—H2AA⋯O1Aⁱⁱ	0.94 (3)	1.85 (3)	2.778 (2)	171 (3)
N3A—H3AA⋯O2A	0.93 (3)	1.78 (3)	2.705 (2)	172 (3)
N1B—H1BA⋯O2Bⁱⁱⁱ	0.84 (3)	2.18 (3)	2.962 (2)	153 (2)
N1B—H1BB⋯O2B^iv	0.90 (3)	2.03 (3)	2.929 (3)	173 (2)
N2B—H2BA⋯O1B^iv	0.95 (3)	1.81 (3)	2.756 (2)	174 (2)
N3B—H3BA⋯O1B^v	0.91 (3)	1.82 (3)	2.728 (2)	171 (2)
Symmetry codes: (i) x, y+1, z; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1; (iv) x, y-1, z; (v) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; 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: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813022204/lh5637sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813022204/lh5637Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813022204/lh5637Isup3.cml

checkCIF report

Comment top

Pyrazoles are an important class of heterocyclic compounds and many pyrazole derivatives are reported to have a broad spectrum of biological properties, e.g. antibacterial and anti-inflammatory activities (Patel et al., 2010), anticancer (Hall et al., 2008), antimicrobial (Samshuddin et al., 2010), anti-inflammatory, antidepressant, anticonvulsant and anti-HIV properties (Isloor et al., 2009). The chemistry of aminopyrazoles has been extensively investigated in the past (Giuseppe et al., 1991). The considerable biological and medicinal activities of pyrazoles (Vinogradov et al., 1994) for which aminopyrazoles are preferred precursors, have stimulated our investigations.

The crystal structures of some related compounds, viz., 3-aminopyrazole-4-carboxylic acid (Dobson & Gerkin, 1998), 4-(3,5-dimethylpyrazol-1-yl)benzoic acid trifluoroacetate (Foces-Foces et al., 1996), 2-amino-5-methylpyridinium trifluoroacetate (Thanigaimani et al., 2012) and 2-amino-5-chloropyridinium trifluoroacetate (Hemamalini & Fun, 2010) have been reported. In view of the importance of the title compound this paper reports its crystal structure.

The asymmetric unit of the title compound consists of two crystallographically independent 3-aminopyrazolium cations (A and B) and two trifluoroacetate anions (A and B) (Fig. 1). Each 3-aminopyrazolium cation is planar, with a maximum deviation of 0.0006 (2) Å for atom N2A in cation A and 0.0005 (2) Å for atom N2B in cation B. In the cations, atoms N3A and N3B are protonated. The F atoms of both anions are disordered over two sets of positions, with occupancy ratios of 0.639 (12):0.361 (12). Bond lengths and are normal (Allen et al., 1987).

In the crystal packing (Fig. 2), the A/B type 3-aminopyrazolium cations interact with the carboxylate groups of the A/B type trifluoroacetate anions through N—H···O hydrogen bonds, forming R₂²(8), R₂⁴(8), R₂⁴(10), R₄⁴(16) and R₄⁴(18) (Bernstein et al., 1995) ring motifs.

Related literature top

For biological properties of pyrazole derivatives, see: Hall et al. (2008); Isloor et al. (2009); Patel et al. (2010); Samshuddin et al. (2010). For the chemistry of aminopyrazoles, see: Giuseppe et al. (1991); For the medicinal activity of pyrazoles, see: Vinogradov et al. (1994). For related structures, see: Dobson & Gerkin (1998); Foces-Foces et al., (1996); Hemamalini & Fun, (2010); Thanigaimani et al. (2012). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995). For standard bond lengths, see: Allen et al. (1987).

Experimental top

A mixture of commercially available 3-aminopyrazole and trifluoroacetic acid (1:3 v/v) were stirred for 15 minutes at room temperature. X-ray quality crystals were formed on slow evaporation. (m.p.: 463-468 K).

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: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. All disorder components are shown.
	Fig. 2. The crystal packing of the title compound, showing the hydrogen bonds (dashed lines) forming chains along [100] and [010]. H atoms not involved in hydrogen bonding and the minor component of disorder have been removed for clarity.

3-Amino-1H-pyrazol-2-ium trifluoroacetate top

Crystal data top

C₃H₆N₃⁺·C₂F₃O₂⁻	F(000) = 800
M_r = 197.13	D_x = 1.681 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.5418 Å
a = 10.9292 (8) Å	Cell parameters from 2544 reflections
b = 10.9332 (6) Å	θ = 3.4–72.4°
c = 13.7002 (13) Å	µ = 1.58 mm⁻¹
β = 107.939 (9)°	T = 173 K
V = 1557.5 (2) Å³	Irregular, colourless
Z = 8	0.16 × 0.14 × 0.06 mm

Data collection top

Agilent Xcalibur (Eos, Gemini) diffractometer	3031 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2343 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 16.0416 pixels mm^-1	θ_max = 72.5°, θ_min = 4.6°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −13→9
T_min = 0.662, T_max = 1.000	l = −15→16
9227 measured reflections

Refinement top

Refinement on F²	Primary atom site location: inferred from neighbouring sites
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	All H-atom parameters refined
wR(F²) = 0.136	w = 1/[σ²(F_o²) + (0.0697P)² + 0.4559P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3031 reflections	Δρ_max = 0.24 e Å⁻³
338 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints

Crystal data top

C₃H₆N₃⁺·C₂F₃O₂⁻	V = 1557.5 (2) Å³
M_r = 197.13	Z = 8
Monoclinic, P2₁/n	Cu Kα radiation
a = 10.9292 (8) Å	µ = 1.58 mm⁻¹
b = 10.9332 (6) Å	T = 173 K
c = 13.7002 (13) Å	0.16 × 0.14 × 0.06 mm
β = 107.939 (9)°

Data collection top

Agilent Xcalibur (Eos, Gemini) diffractometer	3031 independent reflections
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	2343 reflections with I > 2σ(I)
T_min = 0.662, T_max = 1.000	R_int = 0.030
9227 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.136	All H-atom parameters refined
S = 1.05	Δρ_max = 0.24 e Å⁻³
3031 reflections	Δρ_min = −0.23 e Å⁻³
338 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1A	0.56299 (19)	0.93721 (18)	0.25897 (17)	0.0384 (5)
C2A	0.4240 (2)	0.7896 (2)	0.25222 (19)	0.0453 (5)
H2A	0.351 (2)	0.741 (2)	0.2498 (18)	0.050 (7)*
C3A	0.4396 (2)	0.9121 (2)	0.26406 (18)	0.0428 (5)
H3A	0.379 (2)	0.968 (2)	0.2737 (18)	0.050 (7)*
N1A	0.6272 (2)	1.04305 (18)	0.2644 (2)	0.0588 (6)
H1AA	0.593 (3)	1.108 (3)	0.278 (2)	0.057 (8)*
H1AB	0.713 (3)	1.041 (3)	0.272 (2)	0.064 (8)*
N2A	0.61502 (17)	0.83064 (15)	0.24439 (15)	0.0396 (4)
H2AA	0.697 (3)	0.815 (3)	0.240 (2)	0.062 (8)*
N3A	0.52875 (17)	0.73971 (17)	0.23916 (16)	0.0440 (5)
H3AA	0.549 (3)	0.657 (3)	0.236 (2)	0.067 (8)*
C1B	0.28710 (18)	0.17323 (18)	0.48905 (16)	0.0351 (4)
C2B	0.1618 (2)	0.3114 (2)	0.5268 (2)	0.0451 (5)
H2B	0.122 (2)	0.382 (2)	0.5441 (19)	0.050 (7)*
C3B	0.2771 (2)	0.2975 (2)	0.50783 (18)	0.0410 (5)
H3B	0.336 (3)	0.354 (3)	0.508 (2)	0.061 (8)*
N1B	0.37852 (18)	0.11030 (18)	0.46300 (18)	0.0472 (5)
H1BA	0.450 (3)	0.147 (2)	0.476 (2)	0.053 (7)*
H1BB	0.375 (3)	0.029 (3)	0.472 (2)	0.060 (8)*
N2B	0.18060 (15)	0.11865 (16)	0.49623 (14)	0.0372 (4)
H2BA	0.164 (2)	0.034 (3)	0.4985 (19)	0.058 (8)*
N3B	0.10420 (17)	0.20371 (16)	0.52047 (16)	0.0431 (4)
H3BA	0.024 (3)	0.184 (2)	0.5222 (19)	0.051 (7)*
C4A	0.58112 (19)	0.40965 (18)	0.26078 (18)	0.0409 (5)
C5A	0.4574 (2)	0.4142 (2)	0.29303 (18)	0.0422 (5)
F1A1	0.4274 (7)	0.3086 (7)	0.3249 (5)	0.0619 (13)	0.639 (12)
F1A2	0.3945 (12)	0.3073 (14)	0.2818 (12)	0.075 (3)	0.361 (12)
F2A1	0.3589 (8)	0.4515 (8)	0.2173 (6)	0.0681 (17)	0.639 (12)
F2A2	0.3687 (14)	0.4932 (10)	0.2363 (13)	0.067 (3)	0.361 (12)
F3A1	0.4720 (7)	0.4955 (5)	0.3687 (6)	0.0651 (13)	0.639 (12)
F3A2	0.4800 (14)	0.4446 (15)	0.3885 (10)	0.089 (4)	0.361 (12)
O1A	0.63921 (15)	0.31128 (13)	0.27322 (15)	0.0526 (5)
O2A	0.60816 (16)	0.50747 (14)	0.22685 (17)	0.0622 (5)
C4B	0.23375 (19)	0.8115 (2)	0.48329 (18)	0.0413 (5)
C5B	0.2075 (2)	0.6750 (2)	0.45833 (19)	0.0447 (5)
F1B1	0.1329 (4)	0.6255 (3)	0.5045 (6)	0.077 (2)	0.639 (12)
F1B2	0.2028 (16)	0.6103 (8)	0.5367 (6)	0.101 (4)	0.361 (12)
F2B1	0.3162 (3)	0.6097 (3)	0.4866 (5)	0.0669 (13)	0.639 (12)
F2B2	0.2821 (9)	0.6190 (6)	0.4167 (12)	0.089 (4)	0.361 (12)
F3B1	0.1581 (7)	0.6629 (3)	0.3597 (3)	0.090 (2)	0.639 (12)
F3B2	0.0855 (7)	0.6537 (6)	0.3935 (8)	0.079 (3)	0.361 (12)
O1B	0.13834 (14)	0.86991 (13)	0.49109 (15)	0.0530 (5)
O2B	0.34134 (14)	0.84860 (15)	0.48973 (15)	0.0538 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.0374 (10)	0.0299 (10)	0.0508 (12)	0.0050 (8)	0.0177 (9)	0.0021 (8)
C2A	0.0330 (11)	0.0431 (13)	0.0629 (15)	−0.0022 (9)	0.0194 (10)	0.0043 (10)
C3A	0.0351 (10)	0.0382 (12)	0.0595 (14)	0.0072 (9)	0.0208 (10)	0.0022 (10)
N1A	0.0434 (11)	0.0275 (10)	0.113 (2)	0.0008 (8)	0.0358 (12)	−0.0044 (10)
N2A	0.0340 (9)	0.0284 (9)	0.0624 (12)	0.0006 (7)	0.0238 (8)	0.0023 (8)
N3A	0.0385 (9)	0.0281 (9)	0.0701 (13)	−0.0011 (7)	0.0239 (9)	0.0017 (8)
C1B	0.0265 (9)	0.0353 (11)	0.0453 (11)	−0.0029 (7)	0.0138 (8)	0.0041 (8)
C2B	0.0464 (12)	0.0299 (11)	0.0663 (15)	−0.0029 (9)	0.0280 (11)	−0.0050 (10)
C3B	0.0344 (10)	0.0341 (11)	0.0570 (13)	−0.0096 (8)	0.0178 (9)	−0.0010 (9)
N1B	0.0302 (9)	0.0350 (10)	0.0823 (15)	−0.0018 (8)	0.0259 (9)	0.0024 (9)
N2B	0.0288 (8)	0.0279 (9)	0.0588 (11)	−0.0013 (6)	0.0192 (7)	−0.0009 (7)
N3B	0.0345 (9)	0.0330 (9)	0.0709 (13)	−0.0024 (7)	0.0298 (9)	−0.0039 (8)
C4A	0.0354 (10)	0.0301 (11)	0.0639 (14)	−0.0021 (8)	0.0252 (10)	−0.0036 (9)
C5A	0.0363 (11)	0.0397 (12)	0.0549 (13)	−0.0014 (9)	0.0201 (10)	0.0010 (9)
F1A1	0.053 (3)	0.0486 (17)	0.099 (4)	−0.004 (2)	0.045 (3)	0.015 (3)
F1A2	0.046 (5)	0.054 (3)	0.135 (10)	−0.010 (4)	0.044 (5)	0.013 (7)
F2A1	0.0376 (17)	0.094 (5)	0.071 (2)	0.011 (3)	0.0149 (16)	0.019 (3)
F2A2	0.038 (4)	0.058 (5)	0.113 (8)	0.009 (4)	0.035 (5)	0.018 (4)
F3A1	0.061 (2)	0.067 (3)	0.079 (4)	−0.001 (2)	0.039 (2)	−0.027 (2)
F3A2	0.070 (4)	0.137 (11)	0.069 (5)	−0.006 (7)	0.034 (3)	−0.015 (7)
O1A	0.0452 (9)	0.0277 (8)	0.0968 (13)	0.0022 (6)	0.0394 (9)	0.0030 (7)
O2A	0.0526 (10)	0.0302 (8)	0.1222 (16)	0.0029 (7)	0.0538 (11)	0.0110 (9)
C4B	0.0309 (10)	0.0341 (11)	0.0634 (14)	0.0007 (8)	0.0211 (10)	0.0020 (9)
C5B	0.0379 (11)	0.0350 (12)	0.0636 (15)	0.0034 (9)	0.0193 (10)	−0.0015 (10)
F1B1	0.071 (2)	0.0309 (14)	0.151 (6)	−0.0066 (15)	0.068 (3)	0.005 (2)
F1B2	0.174 (11)	0.053 (4)	0.069 (4)	−0.026 (6)	0.025 (6)	0.011 (3)
F2B1	0.0527 (15)	0.0417 (14)	0.107 (3)	0.0162 (11)	0.0249 (19)	−0.0071 (17)
F2B2	0.072 (6)	0.059 (3)	0.163 (11)	−0.002 (3)	0.076 (7)	−0.038 (5)
F3B1	0.113 (5)	0.0658 (19)	0.069 (2)	−0.017 (2)	−0.003 (2)	−0.0142 (14)
F3B2	0.050 (3)	0.060 (3)	0.108 (6)	0.002 (2)	−0.003 (3)	−0.033 (3)
O1B	0.0343 (8)	0.0290 (8)	0.1059 (14)	−0.0020 (6)	0.0366 (8)	−0.0059 (8)
O2B	0.0310 (8)	0.0434 (9)	0.0937 (13)	−0.0013 (6)	0.0290 (8)	0.0035 (8)

Geometric parameters (Å, º) top

C1A—C3A	1.399 (3)	N2B—H2BA	0.95 (3)
C1A—N1A	1.344 (3)	N2B—N3B	1.358 (2)
C1A—N2A	1.338 (3)	N3B—H3BA	0.91 (3)
C2A—H2A	0.96 (3)	C4A—C5A	1.547 (3)
C2A—C3A	1.354 (3)	C4A—O1A	1.234 (2)
C2A—N3A	1.329 (3)	C4A—O2A	1.238 (3)
C3A—H3A	0.94 (3)	C5A—F1A1	1.312 (8)
N1A—H1AA	0.85 (3)	C5A—F1A2	1.341 (14)
N1A—H1AB	0.91 (3)	C5A—F2A1	1.309 (8)
N2A—H2AA	0.94 (3)	C5A—F2A2	1.351 (15)
N2A—N3A	1.357 (2)	C5A—F3A1	1.337 (7)
N3A—H3AA	0.93 (3)	C5A—F3A2	1.298 (14)
C1B—C3B	1.393 (3)	C4B—C5B	1.538 (3)
C1B—N1B	1.349 (3)	C4B—O1B	1.255 (2)
C1B—N2B	1.338 (2)	C4B—O2B	1.221 (2)
C2B—H2B	0.95 (3)	C5B—F1B1	1.295 (5)
C2B—C3B	1.372 (3)	C5B—F1B2	1.299 (8)
C2B—N3B	1.325 (3)	C5B—F2B1	1.337 (4)
C3B—H3B	0.89 (3)	C5B—F2B2	1.284 (6)
N1B—H1BA	0.84 (3)	C5B—F3B1	1.298 (4)
N1B—H1BB	0.90 (3)	C5B—F3B2	1.375 (6)

N1A—C1A—C3A	131.41 (19)	C2B—N3B—N2B	108.01 (17)
N2A—C1A—C3A	107.28 (18)	C2B—N3B—H3BA	130.5 (16)
N2A—C1A—N1A	121.30 (19)	N2B—N3B—H3BA	121.1 (16)
C3A—C2A—H2A	129.0 (15)	O1A—C4A—C5A	116.52 (18)
N3A—C2A—H2A	121.0 (15)	O1A—C4A—O2A	129.27 (19)
N3A—C2A—C3A	109.9 (2)	O2A—C4A—C5A	114.21 (17)
C1A—C3A—H3A	127.7 (15)	F1A1—C5A—C4A	113.4 (4)
C2A—C3A—C1A	106.02 (19)	F1A1—C5A—F3A1	108.0 (4)
C2A—C3A—H3A	126.3 (15)	F1A2—C5A—C4A	113.7 (7)
C1A—N1A—H1AA	118.4 (19)	F1A2—C5A—F2A2	103.9 (7)
C1A—N1A—H1AB	119.1 (18)	F2A1—C5A—C4A	111.2 (4)
H1AA—N1A—H1AB	120 (3)	F2A1—C5A—F1A1	108.0 (4)
C1A—N2A—H2AA	128.8 (18)	F2A1—C5A—F3A1	106.2 (4)
C1A—N2A—N3A	109.00 (17)	F2A2—C5A—C4A	113.1 (7)
N3A—N2A—H2AA	122.2 (18)	F3A1—C5A—C4A	109.7 (3)
C2A—N3A—N2A	107.79 (18)	F3A2—C5A—C4A	112.6 (6)
C2A—N3A—H3AA	129.0 (18)	F3A2—C5A—F1A2	105.7 (7)
N2A—N3A—H3AA	122.6 (18)	F3A2—C5A—F2A2	107.3 (8)
N1B—C1B—C3B	130.75 (19)	O1B—C4B—C5B	114.19 (18)
N2B—C1B—C3B	107.58 (17)	O2B—C4B—C5B	116.60 (19)
N2B—C1B—N1B	121.60 (19)	O2B—C4B—O1B	129.2 (2)
C3B—C2B—H2B	131.0 (15)	F1B1—C5B—C4B	113.5 (3)
N3B—C2B—H2B	119.5 (15)	F1B1—C5B—F2B1	105.8 (3)
N3B—C2B—C3B	109.57 (19)	F1B1—C5B—F3B1	110.1 (3)
C1B—C3B—H3B	125.5 (18)	F1B2—C5B—C4B	113.3 (4)
C2B—C3B—C1B	105.75 (18)	F1B2—C5B—F3B2	99.4 (5)
C2B—C3B—H3B	128.7 (18)	F2B1—C5B—C4B	111.4 (2)
C1B—N1B—H1BA	114.8 (18)	F2B2—C5B—C4B	117.5 (3)
C1B—N1B—H1BB	113.5 (17)	F2B2—C5B—F1B2	107.4 (6)
H1BA—N1B—H1BB	121 (2)	F2B2—C5B—F3B2	104.7 (5)
C1B—N2B—H2BA	128.4 (16)	F3B1—C5B—C4B	108.6 (2)
C1B—N2B—N3B	109.08 (17)	F3B1—C5B—F2B1	107.2 (3)
N3B—N2B—H2BA	121.5 (16)	F3B2—C5B—C4B	112.7 (3)

C1A—N2A—N3A—C2A	−1.0 (3)	O1A—C4A—C5A—F3A2	88.7 (8)
C3A—C1A—N2A—N3A	0.6 (3)	O2A—C4A—C5A—F1A1	177.4 (4)
C3A—C2A—N3A—N2A	1.1 (3)	O2A—C4A—C5A—F1A2	149.4 (7)
N1A—C1A—C3A—C2A	178.8 (3)	O2A—C4A—C5A—F2A1	55.5 (5)
N1A—C1A—N2A—N3A	−178.3 (2)	O2A—C4A—C5A—F2A2	31.3 (7)
N2A—C1A—C3A—C2A	0.1 (3)	O2A—C4A—C5A—F3A1	−61.7 (4)
N3A—C2A—C3A—C1A	−0.7 (3)	O2A—C4A—C5A—F3A2	−90.5 (8)
C1B—N2B—N3B—C2B	1.0 (3)	O1B—C4B—C5B—F1B1	−38.2 (4)
C3B—C1B—N2B—N3B	−0.9 (2)	O1B—C4B—C5B—F1B2	−76.1 (9)
C3B—C2B—N3B—N2B	−0.6 (3)	O1B—C4B—C5B—F2B1	−157.5 (3)
N1B—C1B—C3B—C2B	177.5 (2)	O1B—C4B—C5B—F2B2	157.7 (8)
N1B—C1B—N2B—N3B	−178.2 (2)	O1B—C4B—C5B—F3B1	84.6 (5)
N2B—C1B—C3B—C2B	0.5 (3)	O1B—C4B—C5B—F3B2	35.9 (7)
N3B—C2B—C3B—C1B	0.1 (3)	O2B—C4B—C5B—F1B1	143.9 (4)
O1A—C4A—C5A—F1A1	−3.4 (4)	O2B—C4B—C5B—F1B2	106.0 (9)
O1A—C4A—C5A—F1A2	−31.4 (7)	O2B—C4B—C5B—F2B1	24.5 (4)
O1A—C4A—C5A—F2A1	−125.3 (4)	O2B—C4B—C5B—F2B2	−20.3 (9)
O1A—C4A—C5A—F2A2	−149.5 (6)	O2B—C4B—C5B—F3B1	−93.3 (5)
O1A—C4A—C5A—F3A1	117.5 (4)	O2B—C4B—C5B—F3B2	−142.1 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AA···O1Aⁱ	0.85 (3)	2.28 (3)	2.936 (3)	134 (2)
N1A—H1AB···O2Aⁱⁱ	0.91 (3)	1.99 (3)	2.884 (3)	169 (3)
N2A—H2AA···O1Aⁱⁱ	0.94 (3)	1.85 (3)	2.778 (2)	171 (3)
N3A—H3AA···O2A	0.93 (3)	1.78 (3)	2.705 (2)	172 (3)
N1B—H1BA···O2Bⁱⁱⁱ	0.84 (3)	2.18 (3)	2.962 (2)	153 (2)
N1B—H1BB···O2B^iv	0.90 (3)	2.03 (3)	2.929 (3)	173 (2)
N2B—H2BA···O1B^iv	0.95 (3)	1.81 (3)	2.756 (2)	174 (2)
N3B—H3BA···O1B^v	0.91 (3)	1.82 (3)	2.728 (2)	171 (2)

Symmetry codes: (i) x, y+1, z; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) x, y−1, z; (v) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AA···O1Aⁱ	0.85 (3)	2.28 (3)	2.936 (3)	134 (2)
N1A—H1AB···O2Aⁱⁱ	0.91 (3)	1.99 (3)	2.884 (3)	169 (3)
N2A—H2AA···O1Aⁱⁱ	0.94 (3)	1.85 (3)	2.778 (2)	171 (3)
N3A—H3AA···O2A	0.93 (3)	1.78 (3)	2.705 (2)	172 (3)
N1B—H1BA···O2Bⁱⁱⁱ	0.84 (3)	2.18 (3)	2.962 (2)	153 (2)
N1B—H1BB···O2B^iv	0.90 (3)	2.03 (3)	2.929 (3)	173 (2)
N2B—H2BA···O1B^iv	0.95 (3)	1.81 (3)	2.756 (2)	174 (2)
N3B—H3BA···O1B^v	0.91 (3)	1.82 (3)	2.728 (2)	171 (2)

Symmetry codes: (i) x, y+1, z; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) x, y−1, z; (v) −x, −y+1, −z+1.

Acknowledgements

TSY 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 do research. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England. Google Scholar
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. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Dobson, A. J. & Gerkin, R. E. (1998). Acta Cryst. C54, 253–256. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Foces-Foces, C., Cativiela, C., Zurbano, M. M., Sobrados, I., Jagerovic, N. & Elguero, J. (1996). J. Chem. Crystallogr. 26, 579–584. CAS Google Scholar
Giuseppe, D., Salvatore, P. & Demetrio, R. (1991). Trends Heterocycl. Chem. 2, 97. Google Scholar
Hall, A., Billinton, A., Brown, S. H., Clayton, N. M., Chowdhury, A., Gerald, M. P., Goldsmith, G. P., Hayhow, T. G., Hurst, D. N., Kilford, I. R., Naylor, A. & Passingham, B. (2008). Bioorg. Med. Chem. Lett. 18, 3392–3399. Web of Science CrossRef PubMed CAS Google Scholar
Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o783–o784. Web of Science CrossRef CAS IUCr Journals Google Scholar
Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem. 44, 3784–3787. Web of Science CrossRef PubMed CAS Google Scholar
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790. Web of Science CrossRef CAS IUCr Journals Google Scholar
Patel, C. K., Rami, C. S., Panigrahi, B. & Patel, C. N. (2010). J. Chem. Pharm. Res. 2, 73–78. CAS Google Scholar
Samshuddin, S., Narayana, B., Yathirajan, H. S., Safwan, A. P. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o1279–o1280. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o3319–o3320. CSD CrossRef CAS IUCr Journals Google Scholar
Vinogradov, V. M., Dalinger, I. L. & Shevelev, S. A. (1994). Khim. Farm. Zh. 28, 37–46. CAS Google Scholar