1,1',1'',1'''-(Oxydi-methane-tri-yl)tetra-kis-(4-fluoro-benzene).

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 inter-actions and shows stacking when viewed along the c axis.

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 = 438.40

Triclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.132

S = 1.03

6598 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814005984/bv2231sup1.cif

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

Click here for additional data file.

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

CCDC reference: 992250

Additional supporting information: crystallographic information; 3D view; checkCIF report

C26H18F4O2	Z = 2
Mr = 438.40	F(000) = 452
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0526P)2 + 0.1212P] where P = (Fo2 + 2Fc2)/3
6598 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .