Flunarizinium isonicotinate

Kavitha, C.N.; Kaur, M.; Jasinski, J.P.; Yathirajan, H.S.

doi:10.1107/S1600536814010423

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Pages o681-o682

doi:10.1107/S1600536814010423

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Flunarizinium isonicotinate

Channappa N. Kavitha,^a Manpreet Kaur,^a Jerry P. Jasinski ^b ^* and H. S. Yathirajan ^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

Edited by A. J. Lough, University of Toronto, Canada (Received 26 April 2014; accepted 7 May 2014; online 17 May 2014)

In the cation of the title salt {systematic name: 4-[bis(4-fluorophenyl)methyl]-1-[(2E)-3-phenylprop-2-en-1-yl]piperazin-1-ium pyridine-4-carboxylate}, C₂₆H₂₇F₂N₂⁺·C₆H₄NO₂⁻, the piperazine ring is in a slightly distorted chair conformation. The dihedral angle between the mean planes of the fluoro-substituted benzene rings is 81.9 (1)° and these benzene rings form dihedral angles of 6.5 (1) and 87.8 (1)° with the phenyl ring. In the crystal, a single N—H⋯O hydrogen bond links the cation and the anion. In addition, weak C—H⋯O hydrogen bonds and π–π stacking interactions involving one of the fluoro-substituted benzene rings and the phenyl ring, with a centroid–centroid distance of 3.700 (7) Å, link molecules along [100].

CCDC reference: 1001665

Related literature

For the bioligical activities of flunarizine, see: Amery (1983 ); Holmes et al. (1984 ). For related structures, see: Kavitha et al. (2013a ,b ,c ,d ). For puckering parameters, see Cremer & Pople (1975 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₆H₂₇F₂N₂⁺·C₆H₄NO₂⁻
M_r = 527.60
Monoclinic, P c
a = 11.0023 (3) Å
b = 10.6435 (3) Å
c = 11.3393 (3) Å
β = 92.481 (3)°
V = 1326.63 (6) Å³
Z = 2
Cu Kα radiation
μ = 0.76 mm⁻¹
T = 173 K
0.22 × 0.12 × 0.06 mm

Data collection

Agilent Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ) T_min = 0.781, T_max = 1.000
8232 measured reflections
3403 independent reflections
3238 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.110
S = 1.02
3403 reflections
357 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ), 857 Friedel pairs
Absolute structure parameter: 0.2 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2A⋯O1Bⁱ	0.94 (4)	1.62 (4)	2.557 (3)	176 (4)
C6A—H6A⋯O2Bⁱⁱ	0.93	2.60	3.439 (4)	151
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) x-1, y+1, z.

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 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 1001665

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814010423/lh5702sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814010423/lh5702Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814010423/lh5702Isup3.cml

checkCIF report

Comment top

Flunarizine (1-[bis(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine), a piperazine derivative is a non-selective calcium antagonist (Amery, 1983). It is effective in the prophylaxis of migraine, occlusive peripheral vascular disease, vertigo of central and peripheral origin, and as an adjuvant in the therapy of epilepsy. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic use is published (Holmes et al., 1984). The crystal structures of 4- [bis(4-fluorophenyl)methyl]-1-[(2E)-3-phenylprop-2-en-1-yl]piperazin-1-ium- 3-carboxy propanoate (Kavitha et al., 2013a), flunarizinium hydrogen maleate (Kavitha et al., 2013b), cinnarizinium fumarate (Kavitha et al., 2013c) and cinnarizinium bis(p-toluenesulfonate)dihydrate (Kavitha et al., 2013d) have been reported. In view of the importance of flunarizine, this paper reports the crystal structure study of flunarizinium isonicotinate, (I), C₂₆H₂₇F₂N₂⁺.C₆H₄NO₂^-.

The title salt, (I), crystallizes with one piperazinium cation (A) and one isonicotinate anion (B) in the asymmetric unit (Fig. 1). In the cation, the piperazine ring is in a slightly distorted chair conformation (puckering parameters Q, θ, and ϕ = 0.596 (3)Å, 3.3 (3)° and 10 (4)°, respectively (Cremer & Pople, 1975) and is twisted from the mean plane of the phenyl ring in an anti-periplanar conformation with a torsion angle of -178.9 (7)°. The dihedral angle between the mean planes of the two fluoro-substituted benzene rings is 81.9 (1)°. Of the two fluro-substitutted benzene ring rings, one (C8A–C13A) is almost planar with respect to the mean plane of the phenyl ring forming a diherdral angle of 6.5 (1)°, while the other (C2A–C7A) is twisted by 87.8 (1)°. Bond lengths are in normal ranges (Allen et al., 1987). A single N2A—H2A···O1Bⁱ intermolecular hydrogen bond links the cation with the anion (Fig. 2). In addition, weak C—H···O intermolecular interactions (Table 1) and a weak π–π stacking interaction involving one of the fluoro-substituted benzene rings and the phenyl ring, link the molecules along [100] (Cg1–Cg2 = 3.700 (7)Å; -1+x, 1+y, z; Cg1 = C8A–C13A; Cg2 = C21A–C26A).

Related literature top

For the bioligical activities of flunarizine, see: Amery (1983); Holmes et al. (1984). For related structures, see: Kavitha et al. (2013a,b,c,d). For puckering parameters, see Cremer & Pople (1975). For standard bond lengths, see: Allen et al. (1987).

Experimental top

Flunarizine (2.025 g, 0.01 mol) and isonicotinic acid (0.61 g, 0.005 mol) were dissolved in hot dimethylformamide solution and stirred over a magnetic stirrer for 10 minutes. The resulting solution was allowed to cool slowly at room temperature. The crystals of the title compound appeared after a few days and were subsequently used for x-ray studies.

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

Figures top

	Fig. 1. The asymmetric unit of (I) showing 30% probability displacement ellipsoids.
	Fig. 2. Part of the crystal structure of (I) with hydrogen bonds shown as dashed lines. H atoms not involved in hydrogen bonds have been removed for clarity.

4-[Bis(4-fluorophenyl)methyl]-1-[(2E)-3-phenylprop-2-en-1-yl]piperazin-1-ium pyridine-4-carboxylate top

Crystal data top

C₂₆H₂₇F₂N₂⁺·C₆H₄NO₂⁻	F(000) = 556
M_r = 527.60	D_x = 1.321 Mg m⁻³
Monoclinic, Pc	Cu Kα radiation, λ = 1.54184 Å
a = 11.0023 (3) Å	Cell parameters from 4115 reflections
b = 10.6435 (3) Å	θ = 4.0–71.5°
c = 11.3393 (3) Å	µ = 0.76 mm⁻¹
β = 92.481 (3)°	T = 173 K
V = 1326.63 (6) Å³	Block, colourless
Z = 2	0.22 × 0.12 × 0.06 mm

Data collection top

Agilent Eos Gemini diffractometer	3403 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3238 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm^-1	R_int = 0.042
ω scans	θ_max = 71.3°, θ_min = 4.0°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −13→7
T_min = 0.781, T_max = 1.000	k = −12→13
8232 measured reflections	l = −13→13

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0764P)² + 0.0707P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.040	(Δ/σ)_max < 0.001
wR(F²) = 0.110	Δρ_max = 0.18 e Å⁻³
S = 1.02	Δρ_min = −0.20 e Å⁻³
3403 reflections	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
357 parameters	Extinction coefficient: 0.0050 (8)
2 restraints	Absolute structure: Classical Flack method preferred over Parsons because s.u. lower. 857 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.2 (2)
Hydrogen site location: mixed

Crystal data top

C₂₆H₂₇F₂N₂⁺·C₆H₄NO₂⁻	V = 1326.63 (6) Å³
M_r = 527.60	Z = 2
Monoclinic, Pc	Cu Kα radiation
a = 11.0023 (3) Å	µ = 0.76 mm⁻¹
b = 10.6435 (3) Å	T = 173 K
c = 11.3393 (3) Å	0.22 × 0.12 × 0.06 mm
β = 92.481 (3)°

Data collection top

Agilent Eos Gemini diffractometer	3403 independent reflections
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	3238 reflections with I > 2σ(I)
T_min = 0.781, T_max = 1.000	R_int = 0.042
8232 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	Δρ_max = 0.18 e Å⁻³
S = 1.02	Δρ_min = −0.20 e Å⁻³
3403 reflections	Absolute structure: Classical Flack method preferred over Parsons because s.u. lower. 857 Friedel pairs
357 parameters	Absolute structure parameter: 0.2 (2)
2 restraints

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
F1A	−0.1154 (2)	1.19666 (19)	0.98648 (18)	0.0538 (5)
F2A	0.0248 (2)	1.5040 (2)	0.2592 (2)	0.0696 (7)
N1A	0.2572 (2)	1.0742 (2)	0.58937 (19)	0.0263 (5)
N2A	0.4826 (2)	0.9352 (2)	0.5718 (2)	0.0272 (5)
H2A	0.461 (4)	0.877 (4)	0.513 (4)	0.048 (10)*
C1A	0.1259 (2)	1.0983 (2)	0.5668 (2)	0.0270 (5)
H1A	0.0897	1.0231	0.5298	0.032*
C2A	0.0641 (2)	1.1206 (2)	0.6827 (2)	0.0271 (5)
C3A	0.1256 (3)	1.1748 (2)	0.7798 (2)	0.0291 (5)
H3A	0.2080	1.1932	0.7763	0.035*
C4A	0.0650 (3)	1.2017 (2)	0.8823 (3)	0.0336 (6)
H4A	0.1062	1.2378	0.9472	0.040*
C5A	−0.0561 (3)	1.1741 (3)	0.8856 (3)	0.0362 (6)
C6A	−0.1212 (3)	1.1206 (3)	0.7915 (3)	0.0375 (7)
H6A	−0.2037	1.1033	0.7959	0.045*
C7A	−0.0596 (3)	1.0937 (3)	0.6905 (3)	0.0323 (6)
H7A	−0.1016	1.0569	0.6264	0.039*
C8A	0.1019 (2)	1.2089 (2)	0.4835 (2)	0.0286 (5)
C9A	0.0496 (3)	1.1870 (3)	0.3720 (3)	0.0350 (6)
H9A	0.0320	1.1052	0.3482	0.042*
C10A	0.0231 (3)	1.2866 (4)	0.2952 (3)	0.0441 (8)
H10A	−0.0122	1.2723	0.2204	0.053*
C11A	0.0504 (3)	1.4057 (3)	0.3327 (3)	0.0460 (8)
C12A	0.1034 (3)	1.4311 (3)	0.4423 (3)	0.0454 (8)
H12A	0.1216	1.5132	0.4649	0.054*
C13A	0.1292 (3)	1.3318 (3)	0.5183 (3)	0.0366 (6)
H13A	0.1649	1.3471	0.5927	0.044*
C14A	0.3274 (2)	1.0792 (3)	0.4828 (2)	0.0301 (6)
H14A	0.3156	1.1601	0.4446	0.036*
H14B	0.2991	1.0145	0.4281	0.036*
C15A	0.4611 (3)	1.0600 (3)	0.5144 (2)	0.0297 (6)
H15A	0.5070	1.0650	0.4434	0.036*
H15B	0.4895	1.1261	0.5676	0.036*
C16A	0.4061 (2)	0.9246 (2)	0.6769 (2)	0.0280 (5)
H16A	0.4332	0.9853	0.7362	0.034*
H16B	0.4148	0.8413	0.7108	0.034*
C17A	0.2741 (3)	0.9485 (2)	0.6415 (2)	0.0286 (5)
H17A	0.2463	0.8855	0.5847	0.034*
H17B	0.2253	0.9412	0.7104	0.034*
C18A	0.6153 (3)	0.9189 (3)	0.6037 (3)	0.0338 (6)
H18A	0.6603	0.9180	0.5321	0.041*
H18B	0.6435	0.9900	0.6508	0.041*
C19A	0.6416 (3)	0.8002 (3)	0.6713 (3)	0.0328 (6)
H19A	0.6247	0.7235	0.6349	0.039*
C20A	0.6877 (3)	0.8008 (3)	0.7806 (3)	0.0324 (6)
H20A	0.7019	0.8796	0.8139	0.039*
C21A	0.7198 (2)	0.6926 (3)	0.8567 (2)	0.0306 (6)
C22A	0.7056 (3)	0.5679 (3)	0.8189 (3)	0.0360 (6)
H22A	0.6718	0.5512	0.7440	0.043*
C23A	0.7412 (3)	0.4696 (3)	0.8918 (3)	0.0420 (7)
H23A	0.7306	0.3872	0.8658	0.050*
C24A	0.7929 (3)	0.4928 (3)	1.0041 (3)	0.0439 (7)
H24A	0.8182	0.4263	1.0523	0.053*
C25A	0.8064 (3)	0.6152 (3)	1.0436 (3)	0.0420 (7)
H25A	0.8398	0.6314	1.1188	0.050*
C26A	0.7696 (3)	0.7141 (3)	0.9699 (3)	0.0353 (6)
H26A	0.7785	0.7963	0.9969	0.042*
O1B	0.4163 (2)	0.2192 (2)	0.9087 (2)	0.0479 (6)
O2B	0.5711 (2)	0.1759 (2)	0.7956 (2)	0.0434 (5)
N1B	0.3838 (3)	0.5717 (3)	0.6228 (4)	0.0636 (10)
C1B	0.4838 (3)	0.2391 (3)	0.8226 (2)	0.0326 (6)
C2B	0.4475 (3)	0.3537 (3)	0.7500 (2)	0.0328 (6)
C3B	0.4993 (3)	0.3812 (3)	0.6435 (3)	0.0438 (7)
H3B	0.5574	0.3281	0.6132	0.053*
C4B	0.4628 (4)	0.4892 (4)	0.5830 (3)	0.0604 (11)
H4B	0.4956	0.5046	0.5102	0.072*
C5B	0.3354 (4)	0.5444 (4)	0.7234 (4)	0.0584 (10)
H5B	0.2787	0.6003	0.7518	0.070*
C6B	0.3624 (3)	0.4388 (3)	0.7899 (3)	0.0401 (7)
H6B	0.3244	0.4246	0.8603	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1A	0.0610 (13)	0.0588 (12)	0.0435 (11)	0.0125 (10)	0.0239 (9)	0.0020 (9)
F2A	0.0701 (15)	0.0701 (14)	0.0688 (15)	0.0143 (11)	0.0076 (12)	0.0431 (12)
N1A	0.0251 (11)	0.0285 (10)	0.0256 (11)	0.0021 (8)	0.0031 (8)	0.0020 (8)
N2A	0.0258 (12)	0.0318 (11)	0.0238 (11)	0.0027 (9)	−0.0002 (8)	−0.0024 (9)
C1A	0.0282 (13)	0.0253 (12)	0.0272 (13)	−0.0001 (10)	−0.0023 (10)	−0.0015 (10)
C2A	0.0277 (13)	0.0240 (12)	0.0296 (13)	0.0034 (10)	0.0017 (10)	0.0034 (9)
C3A	0.0301 (13)	0.0258 (12)	0.0316 (13)	0.0011 (10)	0.0017 (10)	0.0002 (9)
C4A	0.0445 (16)	0.0266 (12)	0.0295 (13)	0.0066 (11)	0.0006 (12)	−0.0001 (10)
C5A	0.0448 (17)	0.0306 (13)	0.0345 (14)	0.0099 (12)	0.0149 (12)	0.0086 (11)
C6A	0.0300 (14)	0.0377 (15)	0.0452 (17)	0.0050 (12)	0.0074 (12)	0.0109 (12)
C7A	0.0305 (14)	0.0316 (13)	0.0342 (14)	0.0005 (10)	−0.0029 (11)	0.0066 (11)
C8A	0.0257 (12)	0.0324 (13)	0.0277 (13)	0.0044 (11)	0.0021 (10)	0.0024 (10)
C9A	0.0313 (14)	0.0428 (15)	0.0309 (14)	0.0020 (11)	0.0016 (11)	0.0018 (12)
C10A	0.0341 (16)	0.067 (2)	0.0311 (15)	0.0048 (14)	−0.0008 (12)	0.0123 (14)
C11A	0.0438 (18)	0.0467 (18)	0.0480 (19)	0.0079 (14)	0.0085 (14)	0.0221 (15)
C12A	0.0536 (19)	0.0324 (15)	0.0510 (19)	0.0035 (14)	0.0122 (15)	0.0096 (13)
C13A	0.0435 (17)	0.0324 (15)	0.0340 (15)	0.0027 (12)	0.0029 (12)	0.0029 (11)
C14A	0.0310 (14)	0.0338 (13)	0.0255 (13)	0.0031 (11)	0.0032 (11)	0.0035 (10)
C15A	0.0310 (14)	0.0338 (13)	0.0243 (13)	−0.0010 (11)	0.0036 (10)	0.0020 (10)
C16A	0.0305 (14)	0.0298 (12)	0.0238 (12)	0.0038 (10)	0.0019 (10)	0.0026 (10)
C17A	0.0293 (13)	0.0290 (12)	0.0277 (13)	0.0011 (10)	0.0032 (10)	0.0037 (10)
C18A	0.0260 (14)	0.0421 (15)	0.0332 (15)	0.0021 (11)	0.0007 (11)	−0.0016 (11)
C19A	0.0269 (14)	0.0351 (14)	0.0363 (15)	0.0047 (11)	0.0005 (11)	−0.0066 (11)
C20A	0.0276 (13)	0.0329 (14)	0.0368 (14)	−0.0007 (11)	0.0023 (11)	−0.0035 (11)
C21A	0.0220 (12)	0.0361 (14)	0.0338 (15)	−0.0008 (10)	0.0030 (10)	0.0008 (11)
C22A	0.0325 (15)	0.0396 (15)	0.0357 (15)	−0.0031 (12)	−0.0024 (12)	−0.0045 (12)
C23A	0.0389 (17)	0.0326 (14)	0.0545 (19)	0.0005 (13)	0.0029 (14)	−0.0015 (13)
C24A	0.0395 (17)	0.0445 (17)	0.0476 (18)	0.0031 (13)	0.0013 (14)	0.0131 (14)
C25A	0.0391 (16)	0.0529 (18)	0.0338 (14)	0.0006 (14)	−0.0025 (12)	0.0029 (13)
C26A	0.0339 (15)	0.0368 (15)	0.0351 (15)	−0.0031 (12)	0.0015 (12)	−0.0028 (11)
O1B	0.0465 (13)	0.0533 (13)	0.0444 (13)	0.0075 (11)	0.0073 (10)	0.0189 (10)
O2B	0.0362 (12)	0.0411 (11)	0.0529 (13)	0.0060 (9)	0.0027 (10)	−0.0053 (9)
N1B	0.0457 (18)	0.068 (2)	0.077 (2)	−0.0050 (15)	−0.0011 (16)	0.0407 (18)
C1B	0.0317 (14)	0.0346 (14)	0.0311 (13)	−0.0056 (12)	−0.0023 (11)	−0.0033 (11)
C2B	0.0324 (14)	0.0361 (14)	0.0294 (13)	−0.0091 (11)	−0.0023 (10)	−0.0008 (11)
C3B	0.0436 (17)	0.0529 (18)	0.0353 (15)	−0.0173 (14)	0.0043 (13)	−0.0030 (13)
C4B	0.057 (2)	0.087 (3)	0.0363 (18)	−0.026 (2)	−0.0027 (16)	0.0219 (18)
C5B	0.045 (2)	0.050 (2)	0.081 (3)	0.0008 (16)	0.0043 (19)	0.0200 (19)
C6B	0.0408 (17)	0.0391 (15)	0.0407 (17)	−0.0044 (13)	0.0048 (13)	0.0056 (12)

Geometric parameters (Å, º) top

F1A—C5A	1.363 (3)	C16A—H16A	0.9700
F2A—C11A	1.360 (4)	C16A—H16B	0.9700
N1A—C1A	1.479 (3)	C16A—C17A	1.511 (4)
N1A—C14A	1.463 (3)	C17A—H17A	0.9700
N1A—C17A	1.471 (3)	C17A—H17B	0.9700
N2A—H2A	0.94 (4)	C18A—H18A	0.9700
N2A—C15A	1.493 (3)	C18A—H18B	0.9700
N2A—C16A	1.492 (3)	C18A—C19A	1.499 (4)
N2A—C18A	1.499 (3)	C19A—H19A	0.9300
C1A—H1A	0.9800	C19A—C20A	1.319 (4)
C1A—C2A	1.524 (3)	C20A—H20A	0.9300
C1A—C8A	1.525 (3)	C20A—C21A	1.472 (4)
C2A—C3A	1.392 (4)	C21A—C22A	1.401 (4)
C2A—C7A	1.398 (4)	C21A—C26A	1.393 (4)
C3A—H3A	0.9300	C22A—H22A	0.9300
C3A—C4A	1.395 (4)	C22A—C23A	1.379 (4)
C4A—H4A	0.9300	C23A—H23A	0.9300
C4A—C5A	1.366 (4)	C23A—C24A	1.395 (5)
C5A—C6A	1.381 (5)	C24A—H24A	0.9300
C6A—H6A	0.9300	C24A—C25A	1.383 (5)
C6A—C7A	1.386 (4)	C25A—H25A	0.9300
C7A—H7A	0.9300	C25A—C26A	1.393 (4)
C8A—C9A	1.387 (4)	C26A—H26A	0.9300
C8A—C13A	1.394 (4)	O1B—C1B	1.270 (4)
C9A—H9A	0.9300	O2B—C1B	1.223 (4)
C9A—C10A	1.395 (4)	N1B—C4B	1.329 (6)
C10A—H10A	0.9300	N1B—C5B	1.311 (5)
C10A—C11A	1.366 (5)	C1B—C2B	1.515 (4)
C11A—C12A	1.377 (5)	C2B—C3B	1.388 (4)
C12A—H12A	0.9300	C2B—C6B	1.392 (4)
C12A—C13A	1.385 (4)	C3B—H3B	0.9300
C13A—H13A	0.9300	C3B—C4B	1.389 (6)
C14A—H14A	0.9700	C4B—H4B	0.9300
C14A—H14B	0.9700	C5B—H5B	0.9300
C14A—C15A	1.512 (4)	C5B—C6B	1.379 (5)
C15A—H15A	0.9700	C6B—H6B	0.9300
C15A—H15B	0.9700

C14A—N1A—C1A	113.4 (2)	H15A—C15A—H15B	108.0
C14A—N1A—C17A	107.66 (19)	N2A—C16A—H16A	109.6
C17A—N1A—C1A	109.43 (19)	N2A—C16A—H16B	109.6
C15A—N2A—H2A	104 (2)	N2A—C16A—C17A	110.1 (2)
C15A—N2A—C18A	110.1 (2)	H16A—C16A—H16B	108.2
C16A—N2A—H2A	113 (2)	C17A—C16A—H16A	109.6
C16A—N2A—C15A	109.35 (19)	C17A—C16A—H16B	109.6
C16A—N2A—C18A	112.1 (2)	N1A—C17A—C16A	111.3 (2)
C18A—N2A—H2A	108 (2)	N1A—C17A—H17A	109.4
N1A—C1A—H1A	108.0	N1A—C17A—H17B	109.4
N1A—C1A—C2A	110.3 (2)	C16A—C17A—H17A	109.4
N1A—C1A—C8A	112.5 (2)	C16A—C17A—H17B	109.4
C2A—C1A—H1A	108.0	H17A—C17A—H17B	108.0
C2A—C1A—C8A	110.0 (2)	N2A—C18A—H18A	109.1
C8A—C1A—H1A	108.0	N2A—C18A—H18B	109.1
C3A—C2A—C1A	121.8 (2)	H18A—C18A—H18B	107.8
C3A—C2A—C7A	118.5 (2)	C19A—C18A—N2A	112.7 (2)
C7A—C2A—C1A	119.6 (2)	C19A—C18A—H18A	109.1
C2A—C3A—H3A	119.6	C19A—C18A—H18B	109.1
C2A—C3A—C4A	120.7 (3)	C18A—C19A—H19A	118.8
C4A—C3A—H3A	119.6	C20A—C19A—C18A	122.3 (3)
C3A—C4A—H4A	120.6	C20A—C19A—H19A	118.8
C5A—C4A—C3A	118.7 (3)	C19A—C20A—H20A	115.9
C5A—C4A—H4A	120.6	C19A—C20A—C21A	128.3 (3)
F1A—C5A—C4A	119.2 (3)	C21A—C20A—H20A	115.9
F1A—C5A—C6A	118.0 (3)	C22A—C21A—C20A	122.7 (3)
C4A—C5A—C6A	122.8 (3)	C26A—C21A—C20A	119.1 (2)
C5A—C6A—H6A	121.0	C26A—C21A—C22A	118.1 (3)
C5A—C6A—C7A	117.9 (3)	C21A—C22A—H22A	119.6
C7A—C6A—H6A	121.0	C23A—C22A—C21A	120.7 (3)
C2A—C7A—H7A	119.3	C23A—C22A—H22A	119.6
C6A—C7A—C2A	121.4 (3)	C22A—C23A—H23A	119.8
C6A—C7A—H7A	119.3	C22A—C23A—C24A	120.4 (3)
C9A—C8A—C1A	119.3 (2)	C24A—C23A—H23A	119.8
C9A—C8A—C13A	119.4 (3)	C23A—C24A—H24A	120.1
C13A—C8A—C1A	121.3 (2)	C25A—C24A—C23A	119.7 (3)
C8A—C9A—H9A	119.7	C25A—C24A—H24A	120.1
C8A—C9A—C10A	120.6 (3)	C24A—C25A—H25A	120.2
C10A—C9A—H9A	119.7	C24A—C25A—C26A	119.6 (3)
C9A—C10A—H10A	120.9	C26A—C25A—H25A	120.2
C11A—C10A—C9A	118.3 (3)	C21A—C26A—C25A	121.4 (3)
C11A—C10A—H10A	120.9	C21A—C26A—H26A	119.3
F2A—C11A—C10A	119.1 (3)	C25A—C26A—H26A	119.3
F2A—C11A—C12A	118.1 (3)	C5B—N1B—C4B	116.4 (3)
C10A—C11A—C12A	122.8 (3)	O1B—C1B—C2B	113.8 (3)
C11A—C12A—H12A	120.7	O2B—C1B—O1B	126.3 (3)
C11A—C12A—C13A	118.6 (3)	O2B—C1B—C2B	119.9 (3)
C13A—C12A—H12A	120.7	C3B—C2B—C1B	122.3 (3)
C8A—C13A—H13A	119.9	C3B—C2B—C6B	116.9 (3)
C12A—C13A—C8A	120.3 (3)	C6B—C2B—C1B	120.8 (2)
C12A—C13A—H13A	119.9	C2B—C3B—H3B	120.6
N1A—C14A—H14A	109.7	C2B—C3B—C4B	118.9 (3)
N1A—C14A—H14B	109.7	C4B—C3B—H3B	120.6
N1A—C14A—C15A	110.0 (2)	N1B—C4B—C3B	124.0 (3)
H14A—C14A—H14B	108.2	N1B—C4B—H4B	118.0
C15A—C14A—H14A	109.7	C3B—C4B—H4B	118.0
C15A—C14A—H14B	109.7	N1B—C5B—H5B	117.6
N2A—C15A—C14A	111.0 (2)	N1B—C5B—C6B	124.8 (4)
N2A—C15A—H15A	109.4	C6B—C5B—H5B	117.6
N2A—C15A—H15B	109.4	C2B—C6B—H6B	120.5
C14A—C15A—H15A	109.4	C5B—C6B—C2B	119.0 (3)
C14A—C15A—H15B	109.4	C5B—C6B—H6B	120.5

F1A—C5A—C6A—C7A	−177.8 (2)	C14A—N1A—C1A—C8A	−44.2 (3)
F2A—C11A—C12A—C13A	179.6 (3)	C14A—N1A—C17A—C16A	61.8 (3)
N1A—C1A—C2A—C3A	30.7 (3)	C15A—N2A—C16A—C17A	54.7 (3)
N1A—C1A—C2A—C7A	−153.4 (2)	C15A—N2A—C18A—C19A	175.0 (2)
N1A—C1A—C8A—C9A	112.3 (3)	C16A—N2A—C15A—C14A	−55.8 (3)
N1A—C1A—C8A—C13A	−69.0 (3)	C16A—N2A—C18A—C19A	53.1 (3)
N1A—C14A—C15A—N2A	60.2 (3)	C17A—N1A—C1A—C2A	72.5 (3)
N2A—C16A—C17A—N1A	−59.2 (3)	C17A—N1A—C1A—C8A	−164.4 (2)
N2A—C18A—C19A—C20A	−116.8 (3)	C17A—N1A—C14A—C15A	−61.5 (3)
C1A—N1A—C14A—C15A	177.2 (2)	C18A—N2A—C15A—C14A	−179.3 (2)
C1A—N1A—C17A—C16A	−174.5 (2)	C18A—N2A—C16A—C17A	177.0 (2)
C1A—C2A—C3A—C4A	175.8 (2)	C18A—C19A—C20A—C21A	−179.0 (2)
C1A—C2A—C7A—C6A	−175.5 (2)	C19A—C20A—C21A—C22A	0.9 (4)
C1A—C8A—C9A—C10A	178.0 (3)	C19A—C20A—C21A—C26A	179.0 (3)
C1A—C8A—C13A—C12A	−178.2 (3)	C20A—C21A—C22A—C23A	177.5 (3)
C2A—C1A—C8A—C9A	−124.4 (3)	C20A—C21A—C26A—C25A	−177.2 (3)
C2A—C1A—C8A—C13A	54.3 (3)	C21A—C22A—C23A—C24A	−0.5 (5)
C2A—C3A—C4A—C5A	−0.1 (4)	C22A—C21A—C26A—C25A	1.0 (4)
C3A—C2A—C7A—C6A	0.5 (4)	C22A—C23A—C24A—C25A	1.3 (5)
C3A—C4A—C5A—F1A	178.1 (2)	C23A—C24A—C25A—C26A	−0.9 (5)
C3A—C4A—C5A—C6A	−0.1 (4)	C24A—C25A—C26A—C21A	−0.3 (5)
C4A—C5A—C6A—C7A	0.4 (4)	C26A—C21A—C22A—C23A	−0.6 (4)
C5A—C6A—C7A—C2A	−0.7 (4)	O1B—C1B—C2B—C3B	−171.0 (3)
C7A—C2A—C3A—C4A	−0.1 (4)	O1B—C1B—C2B—C6B	11.0 (4)
C8A—C1A—C2A—C3A	−93.9 (3)	O2B—C1B—C2B—C3B	9.0 (4)
C8A—C1A—C2A—C7A	82.0 (3)	O2B—C1B—C2B—C6B	−169.0 (3)
C8A—C9A—C10A—C11A	0.2 (4)	N1B—C5B—C6B—C2B	0.4 (6)
C9A—C8A—C13A—C12A	0.5 (4)	C1B—C2B—C3B—C4B	−178.9 (3)
C9A—C10A—C11A—F2A	−179.8 (3)	C1B—C2B—C6B—C5B	177.5 (3)
C9A—C10A—C11A—C12A	0.5 (5)	C2B—C3B—C4B—N1B	2.7 (6)
C10A—C11A—C12A—C13A	−0.7 (5)	C3B—C2B—C6B—C5B	−0.6 (5)
C11A—C12A—C13A—C8A	0.1 (5)	C4B—N1B—C5B—C6B	1.2 (6)
C13A—C8A—C9A—C10A	−0.7 (4)	C5B—N1B—C4B—C3B	−2.8 (6)
C14A—N1A—C1A—C2A	−167.3 (2)	C6B—C2B—C3B—C4B	−0.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A···O1Bⁱ	0.94 (4)	1.62 (4)	2.557 (3)	176 (4)
C6A—H6A···O2Bⁱⁱ	0.93	2.60	3.439 (4)	151

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A···O1Bⁱ	0.94 (4)	1.62 (4)	2.557 (3)	176 (4)
C6A—H6A···O2Bⁱⁱ	0.93	2.60	3.439 (4)	151.0

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

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

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