1,4-Bis(benz-yloxy)-2-tert-butyl-benzene.

The title compound, C(24)H(26)O(2), was obtained unintentionally as the product of an attempted synthesis of a new chiral cobalt salen catalyst. There are no classical hydrogen bonds; inter-molecular C-H⋯π stacking inter-actions between aromatic rings help to establish the mol-ecular conformation.

Related literature

For related literature, see: Annis & Jacobsen (1999 ▶); Kwon & Kim (2003 ▶); Ready & Jacobsen (2001 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C24H26O2

M = 346.45

Monoclinic,

a = 6.5570 (13) Å

b = 23.772 (5) Å

c = 12.924 (3) Å

β = 93.21 (3)°

V = 2011.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 (2) K

0.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.969, T max = 0.986

4285 measured reflections

3935 independent reflections

2336 reflections with I > 2σ(I)

R int = 0.027

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.162

S = 1.02

3935 reflections

188 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808003383/rk2077sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003383/rk2077Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H26O2	F000 = 744
Mr = 346.45	Dx = 1.144 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 6.5570 (13) Å	θ = 9–13º
b = 23.772 (5) Å	µ = 0.07 mm−1
c = 12.924 (3) Å	T = 293 (2) K
β = 93.21 (3)º	Block, colourless
V = 2011.3 (7) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.027
Radiation source: fine–focus sealed tube	θmax = 26.0º
Monochromator: graphite	θmin = 1.7º
T = 293(2) K	h = 0→8
ω/2θ scans	k = 0→29
Absorption correction: ψ scan(North et al., 1968)	l = −15→15
Tmin = 0.969, Tmax = 0.986	3 standard reflections
4285 measured reflections	every 200 reflections
3935 independent reflections	intensity decay: none
2336 reflections with I > 2σ(I)

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.072	w = 1/[σ2(Fo2) + (0.0054P)2 + 4.1075P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.162	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.35 e Å−3
3935 reflections	Δρmin = −0.33 e Å−3
188 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0384 (15)
Secondary atom site location: difference Fourier map

Geometry. All s.u.'s (except the s.u.'s 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
C1	1.0565 (4)	0.27733 (12)	0.5023 (3)	0.0843 (15)
H1	1.1645	0.2523	0.5133	0.101*
C2	1.0574 (4)	0.31573 (15)	0.4212 (3)	0.0931 (17)
H2	1.1661	0.3164	0.3780	0.112*
C3	0.8960 (4)	0.35314 (12)	0.4048 (2)	0.0765 (13)
H3	0.8966	0.3788	0.3505	0.092*
C4	0.7335 (4)	0.35215 (11)	0.4694 (2)	0.0582 (11)
C5	0.7326 (4)	0.31375 (13)	0.55046 (19)	0.0719 (13)
H5	0.6239	0.3131	0.5937	0.086*
C6	0.8941 (5)	0.27634 (11)	0.5669 (2)	0.0777 (14)
H6	0.8934	0.2506	0.6212	0.093*
C7	0.5631 (7)	0.3943 (2)	0.4568 (3)	0.0746 (14)
H7A	0.4514	0.3831	0.4984	0.090*
H7B	0.6112	0.4309	0.4806	0.090*
C8	0.3396 (3)	0.43592 (8)	0.32489 (12)	0.0461 (9)
C9	0.2627 (2)	0.43853 (6)	0.22256 (11)	0.0447 (8)
C10	0.1057 (2)	0.47575 (8)	0.19454 (11)	0.0475 (9)
H10	0.0543	0.4775	0.1261	0.057*
C11	0.0255 (3)	0.51035 (8)	0.26886 (14)	0.0486 (9)
C12	0.1024 (3)	0.50774 (8)	0.37119 (13)	0.0530 (10)
H12	0.0487	0.5309	0.4209	0.064*
C13	0.2594 (3)	0.47053 (9)	0.39920 (10)	0.0547 (10)
H13	0.3108	0.4688	0.4677	0.066*
C14	0.3591 (3)	0.40301 (9)	0.13571 (14)	0.0655 (10)
C15	0.2469 (4)	0.41208 (13)	0.02966 (13)	0.0934 (18)
H15A	0.2507	0.4512	0.0118	0.140*
H15B	0.1074	0.4002	0.0326	0.140*
H15C	0.3123	0.3905	−0.0218	0.140*
C16	0.3501 (8)	0.34034 (19)	0.1595 (4)	0.0885 (16)
H16A	0.4201	0.3331	0.2254	0.133*
H16B	0.4145	0.3197	0.1065	0.133*
H16C	0.2101	0.3288	0.1616	0.133*
C17	0.5827 (6)	0.4212 (2)	0.1272 (4)	0.0834 (15)
H17A	0.6565	0.4156	0.1927	0.125*
H17B	0.5875	0.4602	0.1085	0.125*
H17C	0.6439	0.3990	0.0751	0.125*
C18	−0.2037 (6)	0.58533 (19)	0.3026 (3)	0.0689 (13)
H18A	−0.0948	0.6094	0.3307	0.083*
H18B	−0.2610	0.5653	0.3596	0.083*
C19	−0.3651 (2)	0.61998 (7)	0.24720 (11)	0.0528 (10)
C20	−0.3295 (3)	0.67607 (6)	0.2238 (2)	0.0705 (12)
H20	−0.2036	0.6923	0.2422	0.085*
C21	−0.4821 (3)	0.70793 (7)	0.1730 (2)	0.0846 (15)
H21	−0.4583	0.7455	0.1574	0.102*
C22	−0.6703 (3)	0.68368 (9)	0.14560 (14)	0.0824 (15)
H22	−0.7724	0.7050	0.1116	0.099*
C23	−0.7060 (2)	0.62759 (9)	0.1690 (2)	0.0797 (14)
H23	−0.8319	0.6114	0.1506	0.096*
C24	−0.5534 (2)	0.59573 (8)	0.21979 (18)	0.0636 (11)
H24	−0.5772	0.5582	0.2354	0.076*
O1	0.4937 (3)	0.39766 (9)	0.35168 (17)	0.0581 (7)
O2	−0.1255 (2)	0.54656 (6)	0.23203 (9)	0.0577 (7)

	U11	U22	U33	U12	U13	U23
C1	0.061 (3)	0.083 (4)	0.107 (4)	0.019 (3)	−0.014 (3)	0.000 (3)
C2	0.056 (3)	0.102 (4)	0.123 (5)	0.014 (3)	0.013 (3)	0.024 (4)
C3	0.061 (3)	0.078 (3)	0.089 (3)	0.009 (2)	0.002 (2)	0.021 (3)
C4	0.058 (2)	0.070 (2)	0.055 (2)	0.013 (2)	−0.0180 (19)	−0.015 (2)
C5	0.076 (3)	0.084 (3)	0.056 (3)	0.013 (3)	−0.001 (2)	−0.003 (2)
C6	0.096 (4)	0.070 (3)	0.065 (3)	0.014 (3)	−0.014 (3)	0.008 (2)
C7	0.081 (3)	0.082 (3)	0.058 (3)	0.032 (3)	−0.023 (2)	−0.013 (2)
C8	0.0405 (19)	0.051 (2)	0.046 (2)	−0.0003 (17)	−0.0038 (15)	−0.0029 (17)
C9	0.0414 (19)	0.049 (2)	0.0437 (19)	−0.0036 (17)	0.0049 (15)	−0.0008 (16)
C10	0.0413 (19)	0.061 (2)	0.0397 (19)	−0.0004 (18)	−0.0004 (15)	−0.0006 (17)
C11	0.0343 (18)	0.058 (2)	0.053 (2)	−0.0001 (17)	0.0006 (16)	0.0002 (18)
C12	0.057 (2)	0.057 (2)	0.044 (2)	0.0122 (19)	0.0000 (17)	−0.0064 (18)
C13	0.055 (2)	0.066 (3)	0.041 (2)	0.015 (2)	−0.0061 (17)	−0.0015 (18)
C14	0.065 (2)	0.075 (3)	0.057 (2)	0.002 (2)	0.0035 (17)	−0.0086 (19)
C15	0.100 (4)	0.131 (5)	0.049 (3)	0.039 (3)	−0.004 (2)	−0.020 (3)
C16	0.114 (4)	0.071 (3)	0.081 (3)	0.001 (3)	0.009 (3)	−0.021 (3)
C17	0.065 (3)	0.112 (4)	0.076 (3)	0.001 (3)	0.028 (2)	−0.009 (3)
C18	0.066 (3)	0.090 (3)	0.051 (2)	0.032 (2)	−0.001 (2)	−0.004 (2)
C19	0.051 (2)	0.063 (3)	0.045 (2)	0.0094 (19)	0.0053 (17)	−0.0049 (18)
C20	0.069 (3)	0.066 (3)	0.076 (3)	−0.012 (2)	0.000 (2)	−0.012 (2)
C21	0.109 (4)	0.054 (3)	0.091 (4)	0.011 (3)	0.005 (3)	0.008 (3)
C22	0.077 (3)	0.096 (4)	0.073 (3)	0.032 (3)	0.000 (3)	0.010 (3)
C23	0.050 (3)	0.107 (4)	0.082 (3)	0.002 (3)	0.003 (2)	0.004 (3)
C24	0.054 (2)	0.066 (3)	0.072 (3)	0.002 (2)	0.008 (2)	0.007 (2)
O1	0.0566 (16)	0.0708 (18)	0.0461 (14)	0.0190 (14)	−0.0045 (12)	−0.0035 (13)
O2	0.0476 (15)	0.0733 (18)	0.0516 (15)	0.0168 (13)	−0.0015 (12)	−0.0063 (13)

C1—C2	1.3900	C14—C16	1.523 (5)
C1—C6	1.3900	C14—C15	1.5341
C1—H1	0.9300	C14—C17	1.539 (5)
C2—C3	1.3900	C15—H15A	0.9600
C2—H2	0.9300	C15—H15B	0.9600
C3—C4	1.3900	C15—H15C	0.9600
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.3900	C16—H16B	0.9600
C4—C7	1.503 (4)	C16—H16C	0.9600
C5—C6	1.3900	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C7—O1	1.411 (4)	C18—O2	1.413 (4)
C7—H7A	0.9700	C18—C19	1.492 (4)
C7—H7B	0.9700	C18—H18A	0.9700
C8—O1	1.3888	C18—H18B	0.9700
C8—C9	1.3900	C19—C20	1.3900
C8—C13	1.3900	C19—C24	1.3900
C9—C10	1.3900	C20—C21	1.3900
C9—C14	1.5657	C20—H20	0.9300
C10—C11	1.3900	C21—C22	1.3900
C10—H10	0.9300	C21—H21	0.9300
C11—O2	1.3766	C22—C23	1.3900
C11—C12	1.3900	C22—H22	0.9300
C12—C13	1.3900	C23—C24	1.3900
C12—H12	0.9300	C23—H23	0.9300
C13—H13	0.9300	C24—H24	0.9300
C2—C1—C6	120.0	C15—C14—C9	111.8
C2—C1—H1	120.0	C17—C14—C9	108.9 (2)
C6—C1—H1	120.0	C14—C15—H15A	109.5
C1—C2—C3	120.0	C14—C15—H15B	109.5
C1—C2—H2	120.0	H15A—C15—H15B	109.5
C3—C2—H2	120.0	C14—C15—H15C	109.5
C4—C3—C2	120.0	H15A—C15—H15C	109.5
C4—C3—H3	120.0	H15B—C15—H15C	109.5
C2—C3—H3	120.0	C14—C16—H16A	109.5
C5—C4—C3	120.0	C14—C16—H16B	109.5
C5—C4—C7	119.0 (3)	H16A—C16—H16B	109.5
C3—C4—C7	120.9 (3)	C14—C16—H16C	109.5
C4—C5—C6	120.0	H16A—C16—H16C	109.5
C4—C5—H5	120.0	H16B—C16—H16C	109.5
C6—C5—H5	120.0	C14—C17—H17A	109.5
C5—C6—C1	120.0	C14—C17—H17B	109.5
C5—C6—H6	120.0	H17A—C17—H17B	109.5
C1—C6—H6	120.0	C14—C17—H17C	109.5
O1—C7—C4	109.9 (3)	H17A—C17—H17C	109.5
O1—C7—H7A	109.7	H17B—C17—H17C	109.5
C4—C7—H7A	109.7	O2—C18—C19	108.9 (3)
O1—C7—H7B	109.7	O2—C18—H18A	109.9
C4—C7—H7B	109.7	C19—C18—H18A	109.9
H7A—C7—H7B	108.2	O2—C18—H18B	109.9
O1—C8—C9	119.10	C19—C18—H18B	109.9
O1—C8—C13	120.88	H18A—C18—H18B	108.3
C9—C8—C13	120.0	C20—C19—C24	120.0
C10—C9—C8	120.0	C20—C19—C18	120.7 (2)
C10—C9—C14	118.6	C24—C19—C18	119.3 (2)
C8—C9—C14	121.2	C21—C20—C19	120.0
C11—C10—C9	120.0	C21—C20—H20	120.0
C11—C10—H10	120.0	C19—C20—H20	120.0
C9—C10—H10	120.0	C20—C21—C22	120.0
O2—C11—C10	115.07	C20—C21—H21	120.0
O2—C11—C12	124.91	C22—C21—H21	120.0
C10—C11—C12	120.0	C21—C22—C23	120.0
C13—C12—C11	120.0	C21—C22—H22	120.0
C13—C12—H12	120.0	C23—C22—H22	120.0
C11—C12—H12	120.0	C24—C23—C22	120.0
C12—C13—C8	120.0	C24—C23—H23	120.0
C12—C13—H13	120.0	C22—C23—H23	120.0
C8—C13—H13	120.0	C23—C24—C19	120.0
C16—C14—C15	107.2 (2)	C23—C24—H24	120.0
C16—C14—C17	109.7 (3)	C19—C24—H24	120.0
C15—C14—C17	108.0 (2)	C8—O1—C7	117.9 (2)
C16—C14—C9	111.2 (2)	C11—O2—C18	117.68 (19)
C6—C1—C2—C3	0.0	C10—C9—C14—C16	−124.7 (3)
C1—C2—C3—C4	0.0	C8—C9—C14—C16	59.3 (3)
C2—C3—C4—C5	0.0	C10—C9—C14—C15	−4.9
C2—C3—C4—C7	176.5 (3)	C8—C9—C14—C15	179.1
C3—C4—C5—C6	0.0	C10—C9—C14—C17	114.4 (2)
C7—C4—C5—C6	−176.6 (3)	C8—C9—C14—C17	−61.6 (2)
C4—C5—C6—C1	0.0	O2—C18—C19—C20	−107.8 (3)
C2—C1—C6—C5	0.0	O2—C18—C19—C24	72.8 (3)
C5—C4—C7—O1	−135.2 (3)	C24—C19—C20—C21	0.0
C3—C4—C7—O1	48.2 (4)	C18—C19—C20—C21	−179.40 (18)
O1—C8—C9—C10	178.7	C19—C20—C21—C22	0.0
C13—C8—C9—C10	0.0	C20—C21—C22—C23	0.0
O1—C8—C9—C14	−5.3	C21—C22—C23—C24	0.0
C13—C8—C9—C14	176.0	C22—C23—C24—C19	0.0
C8—C9—C10—C11	0.0	C20—C19—C24—C23	0.0
C14—C9—C10—C11	−176.1	C18—C19—C24—C23	179.41 (18)
C9—C10—C11—O2	178.3	C9—C8—O1—C7	−177.5 (3)
C9—C10—C11—C12	0.0	C13—C8—O1—C7	1.2 (4)
O2—C11—C12—C13	−178.2	C4—C7—O1—C8	−178.2 (3)
C10—C11—C12—C13	0.0	C10—C11—O2—C18	−176.0 (2)
C11—C12—C13—C8	0.0	C12—C11—O2—C18	2.3 (3)
O1—C8—C13—C12	−178.7	C19—C18—O2—C11	−179.7 (2)
C9—C8—C13—C12	0.0

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg3i	0.93	2.96	3.725	141
C15—H15C···Cg3ii	0.96	2.87	3.818	168
C24—H24···Cg2iii	0.93	2.71	3.560	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg3i	0.93	2.96	3.725	141
C15—H15C⋯Cg3ii	0.96	2.87	3.818	168
C24—H24⋯Cg2iii	0.93	2.71	3.560	153

Symmetry codes: (i) ; (ii) ; (iii) . Cg2 is the centroid of atoms C8–C13 and Cg3 is the centroid of atoms C19–C24.