1,4-Bis(benz­yloxy)-2-tert-butyl­benzene

Wang, G.; Wu, W.; Zhuang, L.; Wang, J.

doi:10.1107/S1600536808003383

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o620

doi:10.1107/S1600536808003383

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1,4-Bis(benzyloxy)-2-tert-butylbenzene

Guo-wei Wang,^a Wen-yuan Wu,^a Ling-hua Zhuang ^a and Jin-tang Wang ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: wjt@njut.edu.cn

(Received 24 January 2008; accepted 31 January 2008; online 22 February 2008)

The title compound, C₂₄H₂₆O₂, was obtained unintentionally as the product of an attempted synthesis of a new chiral cobalt salen catalyst. There are no classical hydrogen bonds; intermolecular C—H⋯π stacking interactions between aromatic rings help to establish the molecular 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_r = 346.45
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.072
wR(F²) = 0.162
S = 1.02
3935 reflections
188 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.33 e Å⁻³

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) -x, -y+1, -z+1; (ii) -x, -y+1, -z; (iii) x-1, y, z. Cg2 is the centroid of atoms C8–C13 and Cg3 is the centroid of atoms C19–C24.

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.

Supporting information

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

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

checkCIF report

Comment top

Chiral Co(salen) complexes are widely used in the Hydrolytic Kinetic Resolution of terminal epoxides, such as epichlorohydrin (Annis & Jacobsen, 1999). Bis–phenols, such as 2–tert–butyl–hydroquinone, are useful as starting materials for the synthesis of salicylaldehyde (Ready & Jacobsen, 2001), especially in the synthesis of polymeric salen complexes (Kwon & Kim, 2003). We here report the molecular and crystal structure of the title compound (I).

The atom–numbering scheme of (I) is shown in Fig. 1. A l l bond lengths and angles are within normal ranges (Allen et al., 1987). The molecule contains three phenyl rings - ring 1 (C1–C6), ring 2 (C8–C13), ring 3 (C19—C24), which are planar. The dihedral angle between ring 1 and ring 2 is 48.5 (4)°. There are no typical hydrogen bonds, while intermolecular C—H···π stacking interactions between aromatic rings help to stabilize the molecular conformation of compound (I).

Related literature top

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

Experimental top

Under N₂ atmosphere, a mixture of 5.5 g (33 mmol) of 2–tert–butyl–hydroquinone, 2.25 g anhydrous potassium carbonate (16.0 mmol) in 75 ml dry acetonitrile were stirred for half an hour at room temperature. Subsequently 8.2 g (66 mmol) of benzyl chloride and 600 mg (3.6 mmol) of potassium iodide were added to the reaction mixture and was refluxed for 3 h in inert atmosphere. The mixture was cooled to room temperature and was filtrated and the solvent was removed under reduced pressure. The crude product was purified with n–hexane solution. Crystals of (I) suitable for X–ray diffraction were further recrystallized by slow evaporation of acetone. ¹H NMR (CDCl₃, δ, p.p.m.) 7.45 (q, 10H), 7.00 (s, 1H), 6.89 (d, 1H), 6.74 (d, 1H), 5.05 (s, 2H), 4.99 (S, 2H), 1.38 (s, 9H).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of (I) with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. A packing diagram of (I) showing the intermolecular C—H···π interactions (dashed lines). The H atoms not involved in H–bonds are omitted for clarity. Cg2 and Cg3 denote the centroids of the C8–C13 and C19–C24 phenyl rings respectively. [Symmetry codes: (i) -x, -y + 1, -z + 1; (ii) -x, -y + 1, -z; (iii) x - 1, y, z.]

1,4-Bis(benzyloxy)-2-tert-butylbenzene top

Crystal data top

C₂₄H₂₆O₂	F(000) = 744
M_r = 346.45	D_x = 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 = 9–13°
b = 23.772 (5) Å	µ = 0.07 mm⁻¹
c = 12.924 (3) Å	T = 293 K
β = 93.21 (3)°	Block, colourless
V = 2011.3 (7) Å³	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2336 reflections with I > 2σ(I)
Radiation source: fine–focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 26.0°, θ_min = 1.7°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→29
T_min = 0.969, T_max = 0.986	l = −15→15
4285 measured reflections	3 standard reflections every 200 reflections
3935 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.072	H-atom parameters constrained
wR(F²) = 0.162	w = 1/[σ²(F_o²) + (0.0054P)² + 4.1075P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3935 reflections	Δρ_max = 0.35 e Å⁻³
188 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints	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)

Crystal data top

C₂₄H₂₆O₂	V = 2011.3 (7) Å³
M_r = 346.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.5570 (13) Å	µ = 0.07 mm⁻¹
b = 23.772 (5) Å	T = 293 K
c = 12.924 (3) Å	0.40 × 0.30 × 0.20 mm
β = 93.21 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2336 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.027
T_min = 0.969, T_max = 0.986	3 standard reflections every 200 reflections
4285 measured reflections	intensity decay: none
3935 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.03	Δρ_max = 0.35 e Å⁻³
3935 reflections	Δρ_min = −0.33 e Å⁻³
188 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z+1; (ii) −x, −y+1, −z; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₆O₂
M_r	346.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	6.5570 (13), 23.772 (5), 12.924 (3)
β (°)	93.21 (3)
V (Å³)	2011.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.969, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	4285, 3935, 2336
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.162, 1.03
No. of reflections	3935
No. of parameters	188
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.33

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z+1; (ii) −x, −y+1, −z; (iii) x−1, y, z.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

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