1-[Bis(4-fluoro­phen­yl)meth­yl]piperazine

Dayananda, A.S.; Dutkiewicz, G.; Yathirajan, H.S.; Ramesha, A.R.; Kubicki, M.

doi:10.1107/S1600536812036902

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2817

doi:10.1107/S1600536812036902

Open

access

1-[Bis(4-fluorophenyl)methyl]piperazine

A. S. Dayananda,^a Grzegorz Dutkiewicz,^b H. S. Yathirajan,^a A. R. Ramesha ^c and Maciej Kubicki ^b ^*

^aDepartment of Studies in Chemistry, University of Mysore, Mysore 570 006, India, ^bDepartment of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland, and ^cR. L. Fine Chem., Bengaluru 560 064, India
^*Correspondence e-mail: mkubicki@amu.edu.pl

(Received 24 August 2012; accepted 27 August 2012; online 31 August 2012)

In the title molecule, C₁₇H₁₈F₂N₂, the dihedral angle between the benzene rings is 73.40 (3)°. The piperazine ring is close to an ideal chair conformation and the N—H hydrogen is in an equatorial position. In the crystal, molecules are linked via weak C—H⋯F hydrogen bonds.

Related literature

For medical applications of piperazines, see: Bogatcheva et al. (2006 ); Brockunier et al. (2004 ). For related structures, see: Betz et al. (2011a ,b ); Hu et al. (2003 ); Naveen et al. (2006 ). For asymmetry parameters, see: Duax & Norton (1975 ).

Experimental

Crystal data

C₁₇H₁₈F₂N₂
M_r = 288.33
Monoclinic, P 2₁ /c
a = 12.1574 (5) Å
b = 8.8559 (2) Å
c = 13.8604 (4) Å
β = 93.355 (3)°
V = 1489.72 (8) Å³
Z = 4
Cu Kα radiation
μ = 0.77 mm⁻¹
T = 130 K
0.15 × 0.08 × 0.06 mm

Data collection

Atlas SuperNova (Single source at offset) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.828, T_max = 1.000
8816 measured reflections
3006 independent reflections
2847 reflections with I > 2σ(I)
R_int = 0.010

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.096
S = 1.04
3006 reflections
262 parameters
All H-atom parameters refined
Δρ_max = 0.18 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
C25—H25⋯F24ⁱ	0.962 (14)	2.424 (14)	3.2720 (13)	146.8 (10)
C25—H25⋯F34ⁱⁱ	0.962 (14)	2.533 (14)	3.1998 (13)	126.5 (10)
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812036902/mw2085sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812036902/mw2085Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812036902/mw2085Isup3.cml

checkCIF report

Comment top

Piperazine is currently the most important building block used in drug discovery with a high number of positive hits encountered in biological screens of this heterocycle and its congeners. They are found in biologically active compounds across a number of different therapeutic areas such as antifungal, antibacterial, antimalarial, antipsychotic, antidepressant and antitumour activity against colon, prostate, breast, lung and leukemia tumors (Brockunier et al., 2004; Bogatcheva et al., 2006). 1-[bis(4-fluorophenyl)methyl]piperazine is an intermediate for the preparation of flunarizine which is a calcium channel blocker. Here we report the crystal structure of the title compound (I).

Only two structures of neutral 1-benzhydrylpiperazine derivatives have been reported so far: 1-benzhydrylpiperazine itself (Naveen et al., 2006) and (R)-1-((4-chlorophenyl)phenylmethyl)piperazine (Hu et al., 2003) as well as two structures of salts of I, the trinitrophenolate (Betz et al., 2011a) and the 2-(2-phenylethyl)benzoate (Betz et al., 2011b).

The dihedral angle between the mean planes of the p-fluorophenyl rings is 73.40 (3)°. The piperazine ring is in a chair conformation and the asymmetry parameters (Duax & Norton, 1975) are quite small with the largest value for the mirror plane being 3.7° and for the twofold axis 3.0°. The N—H hydrogen atom is in an equatorial position (the C—C—N—H torsion angles are 177° and -176°). In the crystal there are only very weak C—H···F contacts and, interestingly, the shortest contacts to both F atoms are created by the same carbon atom (C25). Therefore it seems that the three-dimensional structure is mainly governed by van der Waals forces.

Related literature top

For medical applications of piperazines, see: Bogatcheva et al. (2006); Brockunier et al. (2004). For related structures, see: Betz et al. (2011a,b); Hu et al. (2003); Naveen et al. (2006). For asymmetry parameters, see: Duax & Norton (1975).

Experimental top

The title compound obtained as a gift sample from R. L. Fine Chem., Bengaluru, India. X-ray quality crystals were grown from a 1:1 (v:v) toluene/hexane solution by slow evaporation (m.p: 360–362 K).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Figure 1. Perspective view of I together with the atom labelling scheme. The ellipsoids are drawn at the 50% probability level and H-atoms are depicted as spheres with arbitrary radii.

1-[Bis(4-fluorophenyl)methyl]piperazine top

Crystal data top

C₁₇H₁₈F₂N₂	F(000) = 608
M_r = 288.33	D_x = 1.286 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 110 reflections
a = 12.1574 (5) Å	θ = 2.9–27.8°
b = 8.8559 (2) Å	µ = 0.77 mm⁻¹
c = 13.8604 (4) Å	T = 130 K
β = 93.355 (3)°	Block, colourless
V = 1489.72 (8) Å³	0.15 × 0.08 × 0.06 mm
Z = 4

Data collection top

Atlas SuperNova (Single source at offset) diffractometer	3006 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2847 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.010
Detector resolution: 10.5357 pixels mm^-1	θ_max = 75.3°, θ_min = 3.6°
ω scan	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −9→10
T_min = 0.828, T_max = 1.000	l = −14→17
8816 measured reflections

Refinement top

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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F²) = 0.096	All H-atom parameters refined
S = 1.04	w = 1/[σ²(F_o²) + (0.0518P)² + 0.3446P] where P = (F_o² + 2F_c²)/3
3006 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₇H₁₈F₂N₂	V = 1489.72 (8) Å³
M_r = 288.33	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 12.1574 (5) Å	µ = 0.77 mm⁻¹
b = 8.8559 (2) Å	T = 130 K
c = 13.8604 (4) Å	0.15 × 0.08 × 0.06 mm
β = 93.355 (3)°

Data collection top

Atlas SuperNova (Single source at offset) diffractometer	3006 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2847 reflections with I > 2σ(I)
T_min = 0.828, T_max = 1.000	R_int = 0.010
8816 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.096	All H-atom parameters refined
S = 1.04	Δρ_max = 0.18 e Å⁻³
3006 reflections	Δρ_min = −0.23 e Å⁻³
262 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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

	x	y	z	U_iso*/U_eq
C1	0.71855 (8)	0.26307 (12)	0.64093 (7)	0.0297 (2)
H1	0.6808 (10)	0.1909 (14)	0.5950 (9)	0.031 (3)*
N11	0.82339 (7)	0.19519 (10)	0.67957 (6)	0.0296 (2)
C12	0.89231 (9)	0.15265 (14)	0.59996 (9)	0.0377 (3)
H12B	0.9123 (11)	0.2450 (16)	0.5634 (10)	0.040 (3)*
H12A	0.8512 (12)	0.0821 (16)	0.5550 (10)	0.044 (4)*
C13	0.99715 (9)	0.07353 (14)	0.63834 (9)	0.0388 (3)
H13B	1.0416 (12)	0.0469 (16)	0.5818 (11)	0.048 (4)*
H13A	1.0429 (11)	0.1472 (16)	0.6811 (10)	0.041 (3)*
N14	0.96894 (8)	−0.06217 (11)	0.69096 (8)	0.0400 (2)
H14	1.0301 (12)	−0.1145 (17)	0.7121 (10)	0.047 (4)*
C15	0.90455 (10)	−0.01932 (14)	0.77224 (10)	0.0428 (3)
H15B	0.9468 (12)	0.0538 (18)	0.8199 (10)	0.050 (4)*
H15A	0.8848 (12)	−0.1141 (18)	0.8085 (11)	0.054 (4)*
C16	0.79931 (9)	0.05778 (13)	0.73443 (10)	0.0388 (3)
H16B	0.7563 (12)	−0.0116 (17)	0.6926 (10)	0.046 (4)*
H16A	0.7553 (11)	0.0865 (16)	0.7897 (10)	0.043 (4)*
C21	0.64243 (8)	0.29345 (11)	0.72207 (7)	0.0282 (2)
C22	0.53738 (9)	0.23052 (12)	0.71842 (9)	0.0343 (2)
H22	0.5114 (11)	0.1663 (16)	0.6633 (10)	0.040 (3)*
C23	0.46608 (9)	0.25595 (13)	0.79170 (9)	0.0379 (3)
H23	0.3926 (13)	0.2108 (17)	0.7896 (11)	0.051 (4)*
C24	0.50228 (9)	0.34553 (12)	0.86750 (8)	0.0344 (2)
F24	0.43371 (6)	0.37247 (9)	0.93966 (5)	0.0496 (2)
C25	0.60588 (9)	0.41045 (12)	0.87452 (8)	0.0324 (2)
H25	0.6270 (11)	0.4725 (16)	0.9295 (10)	0.038 (3)*
C26	0.67547 (8)	0.38383 (12)	0.80075 (8)	0.0299 (2)
H26	0.7491 (12)	0.4266 (15)	0.8047 (10)	0.042 (3)*
C31	0.73448 (8)	0.40781 (12)	0.58434 (7)	0.0301 (2)
C32	0.81328 (9)	0.51586 (13)	0.61203 (8)	0.0369 (3)
H32	0.8644 (12)	0.4954 (16)	0.6675 (10)	0.045 (4)*
C33	0.82205 (10)	0.65060 (14)	0.56149 (9)	0.0418 (3)
H33	0.8754 (13)	0.7275 (19)	0.5793 (11)	0.056 (4)*
C34	0.75027 (10)	0.67407 (13)	0.48296 (9)	0.0401 (3)
F34	0.75839 (7)	0.80528 (9)	0.43211 (6)	0.0570 (2)
C35	0.66997 (10)	0.57242 (15)	0.45345 (8)	0.0426 (3)
H35	0.6225 (13)	0.5946 (19)	0.3972 (12)	0.057 (4)*
C36	0.66273 (9)	0.43910 (14)	0.50508 (8)	0.0370 (3)
H36	0.6086 (12)	0.3684 (17)	0.4860 (10)	0.045 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0265 (5)	0.0272 (5)	0.0352 (5)	−0.0020 (4)	−0.0011 (4)	−0.0051 (4)
N11	0.0259 (4)	0.0261 (4)	0.0369 (5)	0.0014 (3)	0.0034 (3)	−0.0010 (3)
C12	0.0340 (5)	0.0403 (6)	0.0393 (6)	0.0027 (5)	0.0062 (4)	−0.0066 (5)
C13	0.0296 (5)	0.0384 (6)	0.0490 (7)	0.0004 (4)	0.0071 (5)	−0.0099 (5)
N14	0.0278 (5)	0.0288 (5)	0.0634 (6)	0.0031 (4)	0.0023 (4)	−0.0078 (4)
C15	0.0353 (6)	0.0338 (6)	0.0600 (7)	0.0080 (5)	0.0096 (5)	0.0089 (5)
C16	0.0298 (5)	0.0283 (5)	0.0591 (7)	0.0025 (4)	0.0092 (5)	0.0061 (5)
C21	0.0259 (5)	0.0220 (5)	0.0363 (5)	0.0016 (4)	−0.0006 (4)	0.0011 (4)
C22	0.0284 (5)	0.0273 (5)	0.0470 (6)	−0.0023 (4)	−0.0004 (4)	−0.0037 (4)
C23	0.0270 (5)	0.0311 (6)	0.0559 (7)	−0.0020 (4)	0.0051 (5)	0.0017 (5)
C24	0.0328 (5)	0.0287 (5)	0.0426 (6)	0.0060 (4)	0.0104 (4)	0.0056 (4)
F24	0.0458 (4)	0.0492 (4)	0.0562 (4)	0.0006 (3)	0.0237 (3)	−0.0013 (3)
C25	0.0343 (5)	0.0272 (5)	0.0357 (5)	0.0030 (4)	0.0007 (4)	0.0009 (4)
C26	0.0258 (5)	0.0267 (5)	0.0370 (5)	−0.0006 (4)	−0.0008 (4)	0.0010 (4)
C31	0.0291 (5)	0.0300 (5)	0.0312 (5)	0.0015 (4)	0.0028 (4)	−0.0034 (4)
C32	0.0333 (5)	0.0375 (6)	0.0393 (6)	−0.0047 (4)	−0.0035 (4)	0.0048 (5)
C33	0.0365 (6)	0.0373 (6)	0.0518 (7)	−0.0054 (5)	0.0045 (5)	0.0058 (5)
C34	0.0426 (6)	0.0368 (6)	0.0423 (6)	0.0095 (5)	0.0138 (5)	0.0110 (5)
F34	0.0578 (5)	0.0500 (5)	0.0649 (5)	0.0125 (4)	0.0191 (4)	0.0278 (4)
C35	0.0457 (6)	0.0478 (7)	0.0339 (6)	0.0133 (5)	−0.0014 (5)	0.0017 (5)
C36	0.0370 (6)	0.0373 (6)	0.0359 (5)	0.0028 (5)	−0.0041 (4)	−0.0074 (5)

Geometric parameters (Å, º) top

C1—N11	1.4808 (13)	C22—C23	1.3917 (16)
C1—C31	1.5211 (15)	C22—H22	0.989 (14)
C1—C21	1.5216 (14)	C23—C24	1.3684 (17)
C1—H1	0.996 (12)	C23—H23	0.978 (16)
N11—C12	1.4729 (14)	C24—F24	1.3601 (12)
N11—C16	1.4734 (14)	C24—C25	1.3828 (16)
C12—C13	1.5229 (16)	C25—C26	1.3849 (15)
C12—H12B	0.999 (14)	C25—H25	0.962 (14)
C12—H12A	0.996 (15)	C26—H26	0.970 (14)
C13—N14	1.4571 (16)	C31—C36	1.3901 (15)
C13—H13B	1.006 (15)	C31—C32	1.3920 (15)
C13—H13A	1.023 (14)	C32—C33	1.3909 (16)
N14—C15	1.4592 (16)	C32—H32	0.976 (14)
N14—H14	0.909 (15)	C33—C34	1.3706 (17)
C15—C16	1.5164 (16)	C33—H33	0.962 (17)
C15—H15B	1.039 (15)	C34—F34	1.3656 (13)
C15—H15A	1.015 (16)	C34—C35	1.3725 (19)
C16—H16B	0.976 (15)	C35—C36	1.3861 (18)
C16—H16A	0.993 (14)	C35—H35	0.963 (16)
C21—C22	1.3917 (14)	C36—H36	0.935 (15)
C21—C26	1.3928 (15)

N11—C1—C31	113.31 (8)	C22—C21—C26	118.72 (10)
N11—C1—C21	110.63 (8)	C22—C21—C1	119.93 (9)
C31—C1—C21	109.48 (8)	C26—C21—C1	121.35 (9)
N11—C1—H1	109.0 (7)	C21—C22—C23	121.21 (10)
C31—C1—H1	106.2 (7)	C21—C22—H22	120.6 (8)
C21—C1—H1	108.0 (7)	C23—C22—H22	118.2 (8)
C12—N11—C16	108.32 (9)	C24—C23—C22	117.91 (10)
C12—N11—C1	110.38 (8)	C24—C23—H23	120.8 (9)
C16—N11—C1	109.22 (8)	C22—C23—H23	121.3 (9)
N11—C12—C13	110.93 (9)	F24—C24—C23	118.87 (10)
N11—C12—H12B	109.7 (8)	F24—C24—C25	118.05 (10)
C13—C12—H12B	109.3 (8)	C23—C24—C25	123.08 (10)
N11—C12—H12A	110.1 (8)	C24—C25—C26	118.07 (10)
C13—C12—H12A	108.0 (8)	C24—C25—H25	119.6 (8)
H12B—C12—H12A	108.9 (11)	C26—C25—H25	122.4 (8)
N14—C13—C12	109.73 (9)	C25—C26—C21	121.01 (9)
N14—C13—H13B	110.5 (8)	C25—C26—H26	119.6 (8)
C12—C13—H13B	108.2 (8)	C21—C26—H26	119.4 (8)
N14—C13—H13A	111.8 (8)	C36—C31—C32	118.08 (10)
C12—C13—H13A	108.9 (8)	C36—C31—C1	118.86 (9)
H13B—C13—H13A	107.6 (11)	C32—C31—C1	122.92 (9)
C13—N14—C15	108.94 (9)	C33—C32—C31	121.51 (10)
C13—N14—H14	111.7 (9)	C33—C32—H32	119.5 (9)
C15—N14—H14	110.4 (9)	C31—C32—H32	119.0 (9)
N14—C15—C16	109.28 (11)	C34—C33—C32	117.78 (11)
N14—C15—H15B	112.6 (8)	C34—C33—H33	119.0 (9)
C16—C15—H15B	108.4 (8)	C32—C33—H33	123.2 (9)
N14—C15—H15A	108.7 (9)	F34—C34—C33	118.49 (11)
C16—C15—H15A	108.9 (9)	F34—C34—C35	118.42 (11)
H15B—C15—H15A	108.8 (12)	C33—C34—C35	123.09 (11)
N11—C16—C15	111.17 (9)	C34—C35—C36	118.06 (11)
N11—C16—H16B	109.2 (9)	C34—C35—H35	119.3 (10)
C15—C16—H16B	109.5 (9)	C36—C35—H35	122.6 (10)
N11—C16—H16A	108.6 (8)	C35—C36—C31	121.46 (11)
C15—C16—H16A	109.3 (8)	C35—C36—H36	119.3 (9)
H16B—C16—H16A	109.0 (11)	C31—C36—H36	119.3 (9)

C31—C1—N11—C12	−62.03 (11)	C22—C23—C24—C25	−0.37 (17)
C21—C1—N11—C12	174.59 (8)	F24—C24—C25—C26	−179.60 (9)
C31—C1—N11—C16	178.99 (9)	C23—C24—C25—C26	0.45 (16)
C21—C1—N11—C16	55.61 (11)	C24—C25—C26—C21	−0.44 (15)
C16—N11—C12—C13	−56.84 (12)	C22—C21—C26—C25	0.36 (15)
C1—N11—C12—C13	−176.37 (9)	C1—C21—C26—C25	−179.73 (9)
N11—C12—C13—N14	59.56 (12)	N11—C1—C31—C36	145.48 (10)
C12—C13—N14—C15	−60.72 (12)	C21—C1—C31—C36	−90.50 (11)
C13—N14—C15—C16	60.98 (12)	N11—C1—C31—C32	−38.94 (14)
C12—N11—C16—C15	57.53 (13)	C21—C1—C31—C32	85.07 (12)
C1—N11—C16—C15	177.79 (10)	C36—C31—C32—C33	−1.06 (17)
N14—C15—C16—N11	−60.40 (13)	C1—C31—C32—C33	−176.67 (10)
N11—C1—C21—C22	−123.14 (10)	C31—C32—C33—C34	−0.02 (18)
C31—C1—C21—C22	111.29 (10)	C32—C33—C34—F34	−179.48 (10)
N11—C1—C21—C26	56.95 (12)	C32—C33—C34—C35	1.07 (19)
C31—C1—C21—C26	−68.62 (12)	F34—C34—C35—C36	179.60 (10)
C26—C21—C22—C23	−0.28 (16)	C33—C34—C35—C36	−0.95 (18)
C1—C21—C22—C23	179.81 (10)	C34—C35—C36—C31	−0.22 (17)
C21—C22—C23—C24	0.28 (17)	C32—C31—C36—C35	1.19 (17)
C22—C23—C24—F24	179.68 (10)	C1—C31—C36—C35	176.98 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···F24ⁱ	0.962 (14)	2.424 (14)	3.2720 (13)	146.8 (10)
C25—H25···F34ⁱⁱ	0.962 (14)	2.533 (14)	3.1998 (13)	126.5 (10)

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈F₂N₂
M_r	288.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	130
a, b, c (Å)	12.1574 (5), 8.8559 (2), 13.8604 (4)
β (°)	93.355 (3)
V (Å³)	1489.72 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.15 × 0.08 × 0.06

Data collection
Diffractometer	Atlas SuperNova (Single source at offset) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.828, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8816, 3006, 2847
R_int	0.010
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.096, 1.04
No. of reflections	3006
No. of parameters	262
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.23

Computer programs: CrysAlis PRO (Agilent, 2011), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25···F24ⁱ	0.962 (14)	2.424 (14)	3.2720 (13)	146.8 (10)
C25—H25···F34ⁱⁱ	0.962 (14)	2.533 (14)	3.1998 (13)	126.5 (10)

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

Acknowledgements

ASD thanks the University of Mysore for research facilities and HSY thanks R. L. Fine Chem., Bengaluru, for the gift sample.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Betz, R., Gerber, T., Hosten, E., Dayananda, A. S. & Yathirajan, H. S. (2011b). Acta Cryst. E67, o2783–o2784. CrossRef IUCr Journals Google Scholar
Betz, R., Gerber, T., Hosten, E., Dayananda, A. S., Yathirajan, H. S. & Narayana, B. (2011a). Acta Cryst. E67, o2587–o2588. Web of Science CSD CrossRef IUCr Journals Google Scholar
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. Web of Science CrossRef PubMed CAS Google Scholar
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. Web of Science CrossRef PubMed CAS Google Scholar
Duax, W. L. & Norton, D. A. (1975). In Atlas of Steroid Structures. New York: Plenum. Google Scholar
Hu, X.-R., Gu, J.-M. & Lu, G.-L. (2003). Z. Kristallogr. New Cryst. Struct. 218, 497. Google Scholar
Naveen, S., Nanjunda Swamy, S., Basappa, Prabhu Swamy, B., Anandalwar, S. M., Prasad, J. S. & Rangappa, K. S. (2006). Anal. Sci. X-Ray Struct. Anal. Online, 22, x41–x42. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar