1,1′,1′′,1′′′-(Oxydi­methane­tri­yl)tetra­kis­(4-fluoro­benzene)

Roopashree, K.R.; Kavitha, H.D.; Katagi, K.S.; Kotresh, O.; Devarajegowda, H.C.

doi:10.1107/S1600536814005984

organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Page o475

doi:10.1107/S1600536814005984

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1,1′,1′′,1′′′-(Oxydimethanetriyl)tetrakis(4-fluorobenzene)

K. R. Roopashree,^a H. D. Kavitha,^b K. S. Katagi,^c O. Kotresh ^c and H. C. Devarajegowda ^a ^*

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570005, Karnataka, India, ^bDepartment of Physics, Govt. Science College, Hassan 573 201, Karnataka, India, and ^cDepartment of Chemistry, Karnatak Science College, Karnatak University, Dharwad, Karnataka 580001, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 5 February 2014; accepted 18 March 2014; online 26 March 2014)

In the title compound, C₂₆H₁₈F₄O₂, the dihedral angles between pairs of benzene rings linked to the same C atom are 80.55 (8) and 79.11 (7)°. The crystal packing features C—H⋯π interactions and shows stacking when viewed along the c axis.

CCDC reference: 992250

Related literature

For biological applications of the benzhydryl ether unit, see: Brahmachari (2010 ); Weis et al. (2006 ); Van Der Zee & Hespe (1978 ); Nilsson et al. (1969 ); McGavack et al. (1948 ); Loew & Kaiser (1945 ); Pyo et al. (2004 ). For a related structure, see: Devarajegowda et al. (2011 ).

Experimental

Crystal data

C₂₆H₁₈F₄O₂
M_r = 438.40
Triclinic, $[P \overline 1]$
a = 8.1754 (2) Å
b = 8.9536 (2) Å
c = 15.3193 (4) Å
α = 104.965 (2)°
β = 95.175 (2)°
γ = 107.354 (2)°
V = 1016.87 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: ψ scan (SADABS; Sheldrick, 2007 ) T_min = 0.770, T_max = 1.000
24205 measured reflections
6598 independent reflections
4213 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.132
S = 1.03
6598 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C26–C31 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cg4ⁱ	0.93	2.82	3.6834 (17)	154
Symmetry code: (i) x, y-1, z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 992250

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814005984/bv2231sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814005984/bv2231Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814005984/bv2231Isup3.cml

checkCIF report

Comment top

The benzhydryl ether moiety is abundant in a number of naturally occurring and biologically active compounds as well as molecules of potential clinical use and also exhibit various pharmacological potentials. In addition such molecules possess properties such as non-nucleoside reverse transcriptase inhibition (Brahmachari, 2010), anti-plasmodial and anti-trypanosomal action (Weis et al., 2006), monoamine uptake inhibition, anti-depressant and anti-Parkinsonian activity (Van Der Zee & Hespe, 1978; Nilsson et al., 1969), and anti-histaminic (McGavack et al., 1948) and anti-spasmodic (Loew & Kaiser, 1945) action. Naturally occurring symmetrical bis(benzhydryl)ethers are also known to show promising therapeutic potential including significant anti-platelet aggregation efficacy (Pyo et al., 2004). In this article we report the crystal structure of 1,1',1'',1^'''-(oxydimethanetriyl)tetrakis (4-fluorobenzene)

The molecular unit of 1,1',1'',1^'''-(oxydimethanetriyl)tetrakis (4-fluorobenzene) is shown in Fig. 1. The dihedral angles between each pair of benzene rings are 80.55 (8)° [(C6–C11) 1 and (C13–C18) 2] and 79.11 (7)° [(C20–C25) 3 and (C26–C31) 4] respectively. The crystal packing is stabilized by C7—H7···π Cg4[(C26–C31)] interactions and shows stacking when viewed along c axis. The bond distances and bond angles in the benzene ring system are in good agreement with those observed in related structures (Devarajegowda et al., 2011).

Related literature top

For biological applications of the benzhydryl ether unit, see: Brahmachari (2010); Weis et al. (2006); Van Der Zee & Hespe (1978); Nilsson et al. (1969); McGavack et al. (1948); Loew & Kaiser (1945); Pyo et al. (2004). For a related structure, see: Devarajegowda et al. (2011).

Experimental top

An oven-dried screw cap test tube was charged with a magnetic stir bar, benzhydrol (1 mmol), and p-toluenesulfonyl chloride (5 mol%). The tube was then evacuated and back-filled with nitrogen. The evacuation/ backfill sequence was repeated two additional times. The tube was placed in a preheated oil bath at 110°C, and the reaction mixture was stirred vigorously. The progress of the reaction was monitored by TLC, and on completion, the reaction mixture was cooled to room temperature. The reaction mixture was extracted with dried ethyl acetate (10 ml), and the extract was then concentrated under reduced pressure; the residue was purified via column chromatography using silica gel (60 to 120 mesh) and petrol ether-ethyl acetate mixture. white solid, 91% yield, m.p. 363 K.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The packing of molecule of the title compound.

1,1',1'',1'''-(Oxydimethanetriyl)tetrakis(4-fluorobenzene) top

Crystal data top

C₂₆H₁₈F₄O₂	Z = 2
M_r = 438.40	F(000) = 452
Triclinic, P1	D_x = 1.432 Mg m⁻³
Hall symbol: -P 1	Melting point: 363 K
a = 8.1754 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9536 (2) Å	Cell parameters from 3305 reflections
c = 15.3193 (4) Å	θ = 1.5–25.0°
α = 104.965 (2)°	µ = 0.11 mm⁻¹
β = 95.175 (2)°	T = 296 K
γ = 107.354 (2)°	Plate, colourless
V = 1016.87 (4) Å³	0.24 × 0.20 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	6598 independent reflections
Radiation source: fine-focus sealed tube	4213 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω and ϕ scans	θ_max = 31.3°, θ_min = 1.4°
Absorption correction: ψ scan (SADABS; Sheldrick, 2007)	h = −11→11
T_min = 0.770, T_max = 1.000	k = −12→13
24205 measured reflections	l = −22→22

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0526P)² + 0.1212P] where P = (F_o² + 2F_c²)/3
6598 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₆H₁₈F₄O₂	γ = 107.354 (2)°
M_r = 438.40	V = 1016.87 (4) Å³
Triclinic, P1	Z = 2
a = 8.1754 (2) Å	Mo Kα radiation
b = 8.9536 (2) Å	µ = 0.11 mm⁻¹
c = 15.3193 (4) Å	T = 296 K
α = 104.965 (2)°	0.24 × 0.20 × 0.12 mm
β = 95.175 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	6598 independent reflections
Absorption correction: ψ scan (SADABS; Sheldrick, 2007)	4213 reflections with I > 2σ(I)
T_min = 0.770, T_max = 1.000	R_int = 0.030
24205 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.03	Δρ_max = 0.19 e Å⁻³
6598 reflections	Δρ_min = −0.20 e Å⁻³
280 parameters

Special details top

Experimental. IR (νmax, KBr) cm^-1: 3,069, 3,057, 2,925, 1,603, 1,507, 1,422, 1,408, 1,298, 1,225, 1,178, 1,155, 1,101, 1,029, 859, 837, 818. ¹H NMR (CDCl₃, 400 MHz, δ): 7.19 to 7.16 (m, 8H, Ar H), 6.94 to 6.88 (m, 8H, Ar H), 5.22 (s, 2H, CH). 13 C NMR (CDCl₃, 100 MHz, δ): 163.52, 161.07, 137.51, 137.48, 128.82, 128.74, 115.59, 115.38, 78.91. TOF-MS: 445.98 ([M⁺ Na]⁺). Anal. found: C, 73.89; H, 4.28. C₂₆H₁₈F₄O requires C, 73.93; H, 4.30%

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
F1	0.51662 (13)	−0.15696 (11)	0.07690 (7)	0.0851 (3)
F3	1.71199 (12)	0.98406 (12)	0.40107 (7)	0.0887 (3)
F2	0.68830 (14)	0.68143 (15)	0.64449 (6)	0.0910 (3)
F4	0.80529 (13)	0.76746 (12)	−0.09958 (6)	0.0729 (3)
O5	0.91588 (11)	0.58730 (10)	0.26211 (6)	0.0450 (2)
C6	0.61205 (19)	−0.00592 (16)	0.13522 (10)	0.0564 (3)
C7	0.77809 (19)	0.01998 (17)	0.17440 (10)	0.0575 (3)
H7	0.8257	−0.0639	0.1627	0.069*
C8	0.87448 (17)	0.17561 (16)	0.23243 (9)	0.0495 (3)
H8	0.9887	0.1962	0.2594	0.059*
C9	0.80425 (16)	0.29983 (14)	0.25068 (8)	0.0437 (3)
C10	0.63362 (17)	0.26622 (16)	0.20986 (10)	0.0566 (3)
H10	0.5835	0.3483	0.2224	0.068*
C11	0.53683 (18)	0.11302 (17)	0.15099 (11)	0.0611 (4)
H11	0.4232	0.0916	0.1228	0.073*
C12	0.91059 (16)	0.47045 (14)	0.31180 (8)	0.0437 (3)
H12	1.0300	0.4726	0.3286	0.052*
C13	0.84427 (16)	0.52578 (15)	0.39945 (8)	0.0458 (3)
C14	0.75351 (19)	0.41433 (18)	0.44062 (10)	0.0581 (3)
H14	0.7276	0.3027	0.4123	0.070*
C15	0.7006 (2)	0.4656 (2)	0.52311 (10)	0.0665 (4)
H15	0.6397	0.3900	0.5505	0.080*
C16	0.7398 (2)	0.6293 (2)	0.56319 (10)	0.0644 (4)
C17	0.8300 (2)	0.7431 (2)	0.52598 (11)	0.0736 (5)
H17	0.8562	0.8543	0.5553	0.088*
C18	0.8823 (2)	0.69075 (18)	0.44369 (10)	0.0637 (4)
H18	0.9442	0.7679	0.4175	0.076*
C19	1.04230 (15)	0.59122 (14)	0.20239 (8)	0.0436 (3)
H19	1.0426	0.4790	0.1771	0.052*
C20	1.22295 (16)	0.69598 (14)	0.25586 (8)	0.0446 (3)
C21	1.25308 (19)	0.85361 (16)	0.31264 (11)	0.0630 (4)
H21	1.1613	0.8948	0.3175	0.076*
C22	1.4173 (2)	0.95001 (18)	0.36192 (11)	0.0695 (4)
H22	1.4368	1.0549	0.4006	0.083*
C23	1.54990 (19)	0.88794 (18)	0.35260 (10)	0.0607 (4)
C24	1.52757 (19)	0.73525 (19)	0.29736 (10)	0.0610 (4)
H24	1.6210	0.6965	0.2918	0.073*
C25	1.36120 (17)	0.63864 (16)	0.24939 (9)	0.0513 (3)
H25	1.3429	0.5330	0.2121	0.062*
C26	0.98039 (16)	0.64536 (14)	0.12351 (8)	0.0435 (3)
C27	1.09134 (18)	0.75717 (18)	0.08976 (10)	0.0576 (3)
H27	1.2077	0.8060	0.1183	0.069*
C28	1.0337 (2)	0.79841 (18)	0.01455 (11)	0.0629 (4)
H28	1.1099	0.8735	−0.0078	0.076*
C29	0.86398 (19)	0.72695 (16)	−0.02568 (9)	0.0521 (3)
C30	0.74903 (19)	0.6152 (2)	0.00409 (10)	0.0636 (4)
H30	0.6331	0.5672	−0.0252	0.076*
C31	0.80857 (18)	0.57483 (19)	0.07884 (10)	0.0597 (4)
H31	0.7313	0.4982	0.0998	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0678 (6)	0.0598 (5)	0.0926 (7)	0.0021 (4)	0.0069 (5)	−0.0112 (5)
F3	0.0592 (6)	0.0754 (6)	0.1019 (8)	−0.0058 (5)	−0.0223 (5)	0.0227 (5)
F2	0.0886 (7)	0.1324 (9)	0.0540 (5)	0.0475 (7)	0.0217 (5)	0.0158 (6)
F4	0.0851 (6)	0.0804 (6)	0.0610 (5)	0.0351 (5)	0.0057 (5)	0.0285 (5)
O5	0.0444 (5)	0.0434 (4)	0.0515 (5)	0.0155 (4)	0.0136 (4)	0.0186 (4)
C6	0.0527 (8)	0.0478 (7)	0.0547 (8)	0.0039 (6)	0.0114 (6)	0.0066 (6)
C7	0.0586 (8)	0.0500 (7)	0.0621 (8)	0.0206 (6)	0.0145 (7)	0.0096 (6)
C8	0.0451 (7)	0.0522 (7)	0.0503 (7)	0.0174 (6)	0.0061 (5)	0.0133 (6)
C9	0.0419 (6)	0.0438 (6)	0.0452 (6)	0.0117 (5)	0.0066 (5)	0.0165 (5)
C10	0.0443 (7)	0.0476 (7)	0.0758 (9)	0.0143 (6)	0.0032 (6)	0.0188 (6)
C11	0.0416 (7)	0.0569 (8)	0.0737 (9)	0.0063 (6)	−0.0016 (6)	0.0168 (7)
C12	0.0388 (6)	0.0433 (6)	0.0494 (7)	0.0127 (5)	0.0046 (5)	0.0168 (5)
C13	0.0398 (6)	0.0506 (6)	0.0449 (6)	0.0135 (5)	0.0006 (5)	0.0148 (5)
C14	0.0568 (8)	0.0578 (8)	0.0535 (8)	0.0103 (6)	0.0080 (6)	0.0177 (6)
C15	0.0572 (9)	0.0849 (11)	0.0518 (8)	0.0115 (8)	0.0092 (7)	0.0254 (8)
C16	0.0565 (8)	0.0952 (12)	0.0429 (7)	0.0334 (8)	0.0055 (6)	0.0146 (8)
C17	0.0945 (13)	0.0672 (9)	0.0567 (9)	0.0327 (9)	0.0128 (9)	0.0082 (8)
C18	0.0780 (10)	0.0537 (8)	0.0557 (8)	0.0183 (7)	0.0131 (7)	0.0142 (6)
C19	0.0405 (6)	0.0379 (5)	0.0487 (6)	0.0104 (5)	0.0100 (5)	0.0096 (5)
C20	0.0437 (6)	0.0411 (6)	0.0448 (6)	0.0094 (5)	0.0080 (5)	0.0116 (5)
C21	0.0510 (8)	0.0473 (7)	0.0777 (10)	0.0123 (6)	0.0082 (7)	0.0027 (7)
C22	0.0633 (9)	0.0460 (7)	0.0765 (10)	0.0033 (7)	0.0021 (8)	0.0012 (7)
C23	0.0491 (8)	0.0570 (8)	0.0626 (9)	0.0000 (6)	−0.0056 (6)	0.0215 (7)
C24	0.0471 (7)	0.0660 (9)	0.0685 (9)	0.0181 (7)	0.0011 (6)	0.0220 (7)
C25	0.0498 (7)	0.0501 (7)	0.0509 (7)	0.0160 (6)	0.0042 (6)	0.0122 (6)
C26	0.0427 (6)	0.0386 (5)	0.0448 (6)	0.0114 (5)	0.0095 (5)	0.0071 (5)
C27	0.0436 (7)	0.0597 (8)	0.0660 (9)	0.0070 (6)	0.0060 (6)	0.0265 (7)
C28	0.0601 (9)	0.0610 (8)	0.0680 (9)	0.0104 (7)	0.0120 (7)	0.0312 (7)
C29	0.0614 (8)	0.0532 (7)	0.0445 (7)	0.0257 (6)	0.0091 (6)	0.0122 (6)
C30	0.0477 (8)	0.0796 (10)	0.0537 (8)	0.0110 (7)	0.0023 (6)	0.0181 (7)
C31	0.0473 (7)	0.0656 (8)	0.0540 (8)	0.0008 (6)	0.0055 (6)	0.0202 (7)

Geometric parameters (Å, º) top

F1—C6	1.3626 (15)	C17—C18	1.379 (2)
F3—C23	1.3639 (16)	C17—H17	0.9300
F2—C16	1.3628 (16)	C18—H18	0.9300
F4—C29	1.3642 (16)	C19—C26	1.5131 (18)
O5—C12	1.4375 (14)	C19—C20	1.5135 (16)
O5—C19	1.4395 (14)	C19—H19	0.9800
C6—C7	1.360 (2)	C20—C25	1.3751 (19)
C6—C11	1.362 (2)	C20—C21	1.3890 (18)
C7—C8	1.3898 (18)	C21—C22	1.381 (2)
C7—H7	0.9300	C21—H21	0.9300
C8—C9	1.3763 (18)	C22—C23	1.361 (2)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.3865 (18)	C23—C24	1.358 (2)
C9—C12	1.5128 (16)	C24—C25	1.3885 (19)
C10—C11	1.3806 (19)	C24—H24	0.9300
C10—H10	0.9300	C25—H25	0.9300
C11—H11	0.9300	C26—C27	1.3795 (18)
C12—C13	1.5134 (17)	C26—C31	1.3837 (18)
C12—H12	0.9800	C27—C28	1.382 (2)
C13—C18	1.3816 (19)	C27—H27	0.9300
C13—C14	1.3827 (18)	C28—C29	1.352 (2)
C14—C15	1.383 (2)	C28—H28	0.9300
C14—H14	0.9300	C29—C30	1.358 (2)
C15—C16	1.360 (2)	C30—C31	1.378 (2)
C15—H15	0.9300	C30—H30	0.9300
C16—C17	1.354 (2)	C31—H31	0.9300

C12—O5—C19	112.25 (9)	O5—C19—C26	107.41 (10)
C7—C6—C11	122.94 (13)	O5—C19—C20	110.56 (9)
C7—C6—F1	118.79 (13)	C26—C19—C20	114.95 (10)
C11—C6—F1	118.27 (13)	O5—C19—H19	107.9
C6—C7—C8	117.98 (13)	C26—C19—H19	107.9
C6—C7—H7	121.0	C20—C19—H19	107.9
C8—C7—H7	121.0	C25—C20—C21	118.30 (12)
C9—C8—C7	121.28 (13)	C25—C20—C19	121.22 (11)
C9—C8—H8	119.4	C21—C20—C19	120.48 (12)
C7—C8—H8	119.4	C22—C21—C20	120.93 (14)
C8—C9—C10	118.37 (12)	C22—C21—H21	119.5
C8—C9—C12	121.32 (11)	C20—C21—H21	119.5
C10—C9—C12	120.29 (11)	C23—C22—C21	118.46 (14)
C11—C10—C9	121.11 (13)	C23—C22—H22	120.8
C11—C10—H10	119.4	C21—C22—H22	120.8
C9—C10—H10	119.4	C24—C23—C22	122.88 (13)
C6—C11—C10	118.30 (13)	C24—C23—F3	118.94 (15)
C6—C11—H11	120.9	C22—C23—F3	118.19 (14)
C10—C11—H11	120.9	C23—C24—C25	118.05 (14)
O5—C12—C9	109.77 (9)	C23—C24—H24	121.0
O5—C12—C13	108.00 (9)	C25—C24—H24	121.0
C9—C12—C13	114.58 (10)	C20—C25—C24	121.37 (13)
O5—C12—H12	108.1	C20—C25—H25	119.3
C9—C12—H12	108.1	C24—C25—H25	119.3
C13—C12—H12	108.1	C27—C26—C31	117.42 (13)
C18—C13—C14	117.97 (13)	C27—C26—C19	122.56 (11)
C18—C13—C12	120.56 (12)	C31—C26—C19	119.91 (11)
C14—C13—C12	121.36 (12)	C26—C27—C28	121.57 (13)
C13—C14—C15	121.28 (14)	C26—C27—H27	119.2
C13—C14—H14	119.4	C28—C27—H27	119.2
C15—C14—H14	119.4	C29—C28—C27	118.40 (13)
C16—C15—C14	118.31 (14)	C29—C28—H28	120.8
C16—C15—H15	120.8	C27—C28—H28	120.8
C14—C15—H15	120.8	C28—C29—C30	122.66 (13)
C17—C16—C15	122.50 (14)	C28—C29—F4	118.94 (13)
C17—C16—F2	118.62 (16)	C30—C29—F4	118.40 (13)
C15—C16—F2	118.88 (15)	C29—C30—C31	118.27 (13)
C16—C17—C18	118.76 (15)	C29—C30—H30	120.9
C16—C17—H17	120.6	C31—C30—H30	120.9
C18—C17—H17	120.6	C30—C31—C26	121.68 (13)
C17—C18—C13	121.17 (15)	C30—C31—H31	119.2
C17—C18—H18	119.4	C26—C31—H31	119.2
C13—C18—H18	119.4

C11—C6—C7—C8	−0.5 (2)	C12—O5—C19—C26	152.38 (9)
F1—C6—C7—C8	178.88 (12)	C12—O5—C19—C20	−81.48 (11)
C6—C7—C8—C9	0.6 (2)	O5—C19—C20—C25	129.54 (12)
C7—C8—C9—C10	0.2 (2)	C26—C19—C20—C25	−108.67 (13)
C7—C8—C9—C12	−178.35 (12)	O5—C19—C20—C21	−50.75 (16)
C8—C9—C10—C11	−1.1 (2)	C26—C19—C20—C21	71.04 (15)
C12—C9—C10—C11	177.40 (13)	C25—C20—C21—C22	−0.5 (2)
C7—C6—C11—C10	−0.4 (2)	C19—C20—C21—C22	179.81 (14)
F1—C6—C11—C10	−179.81 (13)	C20—C21—C22—C23	0.9 (3)
C9—C10—C11—C6	1.3 (2)	C21—C22—C23—C24	−0.3 (3)
C19—O5—C12—C9	−80.08 (11)	C21—C22—C23—F3	179.66 (14)
C19—O5—C12—C13	154.36 (9)	C22—C23—C24—C25	−0.7 (2)
C8—C9—C12—O5	122.12 (12)	F3—C23—C24—C25	179.29 (13)
C10—C9—C12—O5	−56.39 (15)	C21—C20—C25—C24	−0.6 (2)
C8—C9—C12—C13	−116.18 (13)	C19—C20—C25—C24	179.09 (12)
C10—C9—C12—C13	65.31 (15)	C23—C24—C25—C20	1.2 (2)
O5—C12—C13—C18	−32.95 (16)	O5—C19—C26—C27	137.23 (12)
C9—C12—C13—C18	−155.61 (13)	C20—C19—C26—C27	13.75 (17)
O5—C12—C13—C14	151.03 (12)	O5—C19—C26—C31	−46.67 (15)
C9—C12—C13—C14	28.37 (16)	C20—C19—C26—C31	−170.15 (12)
C18—C13—C14—C15	0.6 (2)	C31—C26—C27—C28	0.4 (2)
C12—C13—C14—C15	176.73 (13)	C19—C26—C27—C28	176.56 (13)
C13—C14—C15—C16	0.1 (2)	C26—C27—C28—C29	0.4 (2)
C14—C15—C16—C17	−0.8 (2)	C27—C28—C29—C30	−0.9 (2)
C14—C15—C16—F2	179.99 (13)	C27—C28—C29—F4	179.57 (13)
C15—C16—C17—C18	0.8 (3)	C28—C29—C30—C31	0.6 (2)
F2—C16—C17—C18	−179.99 (14)	F4—C29—C30—C31	−179.86 (13)
C16—C17—C18—C13	−0.1 (3)	C29—C30—C31—C26	0.2 (2)
C14—C13—C18—C17	−0.6 (2)	C27—C26—C31—C30	−0.7 (2)
C12—C13—C18—C17	−176.76 (14)	C19—C26—C31—C30	−176.97 (13)

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C26–C31 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg4ⁱ	0.93	2.82	3.6834 (17)	154

Symmetry code: (i) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C26–C31 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg4ⁱ	0.93	2.82	3.6834 (17)	154

Symmetry code: (i) x, y−1, z.

Acknowledgements

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the CCD X-ray facilities, X-ray data collection and GCMS, IR, CHNS and NMR data.

References

Brahmachari, G. (2010). Handbook of Pharmaceutical Natural Products, 1st ed. Weinheim: Wiley–VCH. Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Devarajegowda, H. C., Arunkashi, H. K., Vepuri, S. B., Chidananda, N. & Prasad, V. D. J. (2011). Acta Cryst. E67, o564. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Loew, E. R. & Kaiser, M. E. (1945). Exp. Biol. Med. 58, 235–237. CrossRef CAS Google Scholar
McGavack, T. H., Schulman, P. M. & Boyd, L. J. (1948). J. Allergy, 19, 141–145. CrossRef PubMed Web of Science Google Scholar
Nilsson, J. L., Wagermark, J. & Dahlbom, R. (1969). J. Med. Chem. 12, 1103–1105. CrossRef CAS PubMed Web of Science Google Scholar
Pyo, M. K., Jin, J. L., Koo, Y. K. & Yun-Choi, S. (2004). Arch. Pharm. Res. 27, 381–385. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin,USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Van Der Zee, P. & Hespe, W. (1978). Neuropharmacology, 17, 483–490. CrossRef CAS PubMed Web of Science Google Scholar
Weis, R., Schlapper, C., Brun, C. R., Kaiser, M. & Seebacher, W. (2006). Eur. J. Pharm. Sci. 28, 361–368. Web of Science CrossRef PubMed CAS Google Scholar

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