2,2′,4,4′,6,6′-Hexamethyl­biphenyl-3,3′,5,5′-tetra­yltetra­methyl­ene tetra­acetate

Hu, T.

doi:10.1107/S1600536809018261

organic compounds

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Volume 65| Part 6| June 2009| Page o1355

doi:10.1107/S1600536809018261

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2,2′,4,4′,6,6′-Hexamethylbiphenyl-3,3′,5,5′-tetrayltetramethylene tetraacetate

Tuoping Hu ^a ^*

^aDepartment of Chemistry, North University of China, Taiyuan, Shanxi 030051, People's Republic of China
^*Correspondence e-mail: hutuopingsx@yahoo.com.cn

(Received 6 April 2009; accepted 14 May 2009; online 20 May 2009)

The title compound, C₃₀H₃₈O₈, possess C_i symmetry, with the inversion center situated at the center of the bridging C—C bond. In the crystal structure, molecules are held together by C—H⋯O interactions.

Related literature

For related structures, see: Frohlich & Musso (1985 ), Moorthy et al. (2002 , 2005 , 2006a ,b ); Natarajan et al. (2005a ,b ); Pickett (1936 ).

Experimental

Crystal data

C₃₀H₃₈O₈
M_r = 526.60
Orthorhombic, I b a 2
a = 15.336 (2) Å
b = 12.658 (1) Å
c = 14.755 (2) Å
V = 2864.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.983, T_max = 0.991
8052 measured reflections
1709 independent reflections
1045 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.199
S = 1.02
1709 reflections
173 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O1ⁱ	0.96	2.58	3.472 (7)	155
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; 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/S1600536809018261/su2107sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809018261/su2107Isup2.hkl

checkCIF report

Comment top

The title compound, illustrated in Fig. 1, was obtained as a byproduct when preparing the first order dendrimer by using 2,2',4,4',6,6'-hexamethyl-3,3',5,5''-biphenylene- tetramethanol. The molecule possesses a centre of inversion situated at the center of the bridging C-C bond. The two benzene rings are almost perpendicular to one another, with a dihedral angle of 82.71 (2) °. The geometry and bond distances are close to those observed in similar structures (Frohlich et al., 1985); Moorthy et al., 2002, 2005, 2006a,b; Natarajan et al., 2005a,b; Pickett, 1936).

In the crystal structure of the title compound adjacent molecules have normal hydrophobic contacts with no intercalation or stacking interactions, only C-H···O interactions (Table 1 and Fig. 2).

Related literature top

For related structures, see: Frohlich et al. (1985), Moorthy et al. (2002, 2005, 2006a,b); Natarajan et al. (2005a,b); Pickett (1936).

Experimental top

To (2,2',4,4',6,6'-trimethyl-1,1',3,3'-phenylene) tetramethanol (10 mmol, 3.585 mg), in 50 ml of CH₃COOH, was added 5 g of KOH. The mixture was stirred and heated at reflux for 24 h. The solution was then filtered, and the filtrate concentrated under vacumn. The sticky solid obtained was recrystalized in a mixture of benzene and acetone (1:1). Colourless prismatic crystals of the title compound were obtained. They were filtered, washed with cool diethylether and air dried.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); 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. Molecular structure of the title compound, showing 50% probability displacement ellipsoids. The atoms marked with A are derived from the reference atoms by means of the symmetry transformation (1 -x, -y, z) .
	Fig. 2. Crystal packing of the title compound viewed along the c axis.

2,2',4,4',6,6'-Hexamethylbiphenyl-3,3',5,5'-tetrayltetramethylene tetraacetate top

Crystal data top

C₃₀H₃₈O₈	F(000) = 1128
M_r = 526.60	D_x = 1.221 Mg m⁻³
Orthorhombic, Iba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I 2 -2 c	Cell parameters from 1604 reflections
a = 15.336 (2) Å	θ = 2.3–22.7°
b = 12.658 (1) Å	µ = 0.09 mm⁻¹
c = 14.755 (2) Å	T = 293 K
V = 2864.3 (6) Å³	Prism, colorless
Z = 4	0.20 × 0.10 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1709 independent reflections
Radiation source: fine-focus sealed tube	1045 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ϕ and ω scans	θ_max = 27.6°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→17
T_min = 0.983, T_max = 0.991	k = −16→12
8052 measured reflections	l = −19→18

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.199	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.1286P)²] where P = (F_o² + 2F_c²)/3
1709 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.21 e Å⁻³
2 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₃₀H₃₈O₈	V = 2864.3 (6) Å³
M_r = 526.60	Z = 4
Orthorhombic, Iba2	Mo Kα radiation
a = 15.336 (2) Å	µ = 0.09 mm⁻¹
b = 12.658 (1) Å	T = 293 K
c = 14.755 (2) Å	0.20 × 0.10 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1709 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1045 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.991	R_int = 0.046
8052 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	2 restraints
wR(F²) = 0.199	H-atom parameters constrained
S = 1.02	Δρ_max = 0.21 e Å⁻³
1709 reflections	Δρ_min = −0.14 e Å⁻³
173 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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 > σ(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
O1	0.5866 (2)	0.3433 (3)	−0.0969 (2)	0.0833 (12)
O2	0.22394 (19)	0.1664 (3)	0.1133 (2)	0.0781 (12)
O3	0.6098 (3)	0.4057 (4)	−0.2354 (3)	0.1157 (19)
O4	0.1730 (3)	0.2011 (6)	0.2488 (4)	0.140 (2)
C1	0.3745 (2)	0.1758 (4)	0.0700 (3)	0.0633 (13)
C2	0.4014 (3)	0.2522 (4)	0.0068 (4)	0.0670 (16)
C3	0.4673 (3)	0.2301 (3)	−0.0546 (3)	0.0627 (14)
C4	0.5069 (3)	0.1309 (3)	−0.0540 (3)	0.0595 (11)
C5	0.4793 (2)	0.0532 (3)	0.0067 (3)	0.0542 (11)
C6	0.4117 (2)	0.0748 (4)	0.0680 (2)	0.0565 (13)
C7	0.3093 (3)	0.2018 (5)	0.1427 (4)	0.0867 (18)
C8	0.3548 (5)	0.3593 (5)	0.0064 (7)	0.116 (3)
C9	0.4985 (4)	0.3108 (4)	−0.1239 (4)	0.0833 (16)
C10	0.5800 (4)	0.1052 (4)	−0.1200 (4)	0.0813 (17)
C11	0.3798 (3)	−0.0116 (5)	0.1307 (3)	0.0773 (16)
C12	0.1610 (3)	0.1719 (4)	0.1736 (3)	0.0737 (17)
C13	0.6365 (3)	0.3889 (4)	−0.1602 (4)	0.0687 (17)
C14	0.7248 (3)	0.4091 (5)	−0.1300 (4)	0.088 (2)
C15	0.0765 (3)	0.1341 (6)	0.1374 (4)	0.096 (2)
H7A	0.32520	0.16690	0.19880	0.1040*
H7B	0.30840	0.27740	0.15330	0.1040*
H8A	0.35990	0.39140	0.06510	0.1730*
H8B	0.29430	0.34920	−0.00790	0.1730*
H8C	0.38110	0.40440	−0.03820	0.1730*
H9A	0.49950	0.27960	−0.18400	0.1000*
H9B	0.45970	0.37130	−0.12480	0.1000*
H10A	0.59200	0.16590	−0.15690	0.1220*
H10B	0.56270	0.04730	−0.15800	0.1220*
H10C	0.63150	0.08610	−0.08670	0.1220*
H11A	0.41300	−0.07480	0.12030	0.1160*
H11B	0.31930	−0.02530	0.11910	0.1160*
H11C	0.38710	0.01040	0.19250	0.1160*
H14A	0.73100	0.38720	−0.06810	0.1320*
H14B	0.73710	0.48320	−0.13490	0.1320*
H14C	0.76490	0.37020	−0.16720	0.1320*
H15A	0.08300	0.11650	0.07440	0.1430*
H15B	0.03350	0.18860	0.14380	0.1430*
H15C	0.05830	0.07250	0.17040	0.1430*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.067 (2)	0.109 (2)	0.074 (2)	−0.0219 (18)	−0.0067 (17)	0.0083 (19)
O2	0.0487 (14)	0.123 (3)	0.0627 (17)	0.0076 (16)	0.0032 (14)	−0.0154 (17)
O3	0.100 (3)	0.149 (4)	0.098 (3)	−0.014 (3)	−0.013 (3)	0.043 (3)
O4	0.098 (3)	0.226 (6)	0.096 (3)	−0.051 (3)	0.036 (3)	−0.067 (4)
C1	0.0368 (18)	0.090 (3)	0.063 (2)	0.0000 (19)	−0.0031 (17)	−0.021 (2)
C2	0.054 (2)	0.069 (3)	0.078 (3)	0.007 (2)	−0.009 (2)	−0.010 (2)
C3	0.052 (2)	0.074 (3)	0.062 (2)	−0.0011 (19)	−0.008 (2)	0.002 (2)
C4	0.0474 (19)	0.079 (2)	0.052 (2)	0.0014 (19)	0.0024 (17)	−0.0007 (19)
C5	0.0443 (19)	0.068 (2)	0.0502 (19)	0.0035 (16)	−0.0030 (16)	0.0004 (19)
C6	0.0395 (17)	0.082 (3)	0.048 (2)	−0.0061 (18)	0.0007 (15)	−0.0087 (19)
C7	0.057 (2)	0.124 (4)	0.079 (3)	0.003 (3)	0.001 (2)	−0.033 (3)
C8	0.097 (4)	0.085 (4)	0.165 (7)	0.033 (3)	−0.005 (5)	−0.007 (4)
C9	0.066 (2)	0.093 (3)	0.091 (3)	−0.010 (3)	−0.015 (2)	0.023 (3)
C10	0.076 (3)	0.092 (3)	0.076 (3)	0.006 (2)	0.026 (3)	0.007 (3)
C11	0.063 (2)	0.100 (3)	0.069 (3)	−0.007 (3)	0.015 (2)	0.003 (3)
C12	0.069 (3)	0.091 (3)	0.061 (3)	0.002 (2)	0.011 (2)	−0.007 (2)
C13	0.076 (3)	0.067 (3)	0.063 (3)	0.001 (2)	0.000 (2)	0.005 (2)
C14	0.072 (3)	0.102 (4)	0.090 (4)	−0.017 (3)	−0.002 (3)	−0.003 (3)
C15	0.060 (3)	0.151 (5)	0.076 (3)	−0.005 (3)	0.007 (2)	0.002 (3)

Geometric parameters (Å, º) top

O1—C9	1.468 (7)	C7—H7A	0.9700
O1—C13	1.338 (6)	C7—H7B	0.9700
O2—C7	1.450 (6)	C8—H8A	0.9600
O2—C12	1.315 (5)	C8—H8B	0.9600
O3—C13	1.202 (7)	C8—H8C	0.9600
O4—C12	1.184 (8)	C9—H9A	0.9700
C1—C2	1.405 (7)	C9—H9B	0.9700
C1—C6	1.400 (7)	C10—H10A	0.9600
C1—C7	1.503 (7)	C10—H10B	0.9600
C2—C3	1.386 (7)	C10—H10C	0.9600
C2—C8	1.533 (8)	C11—H11A	0.9600
C3—C4	1.395 (6)	C11—H11B	0.9600
C3—C9	1.523 (7)	C11—H11C	0.9600
C4—C5	1.396 (6)	C14—H14A	0.9600
C4—C10	1.520 (7)	C14—H14B	0.9600
C5—C6	1.403 (5)	C14—H14C	0.9600
C5—C5ⁱ	1.489 (5)	C15—H15A	0.9600
C6—C11	1.514 (7)	C15—H15B	0.9600
C12—C15	1.481 (7)	C15—H15C	0.9600
C13—C14	1.448 (7)

O1···C10	3.035 (6)	H7A···C11	2.6100
O2···C11	3.295 (6)	H7A···H11C	2.2000
O3···C7ⁱⁱ	3.382 (8)	H7A···H10A^vii	2.4800
O4···C9ⁱⁱⁱ	3.236 (8)	H7B···O4	2.6900
O1···H15A^iv	2.5800	H7B···C8	2.5100
O1···H10A	2.4200	H7B···H8A	2.1000
O2···H11B	2.8300	H7B···H8B	2.5600
O2···H14A^v	2.7600	H7B···O3^vii	2.6300
O3···H9A	2.4500	H8A···C7	2.7700
O3···H7Bⁱⁱ	2.6300	H8A···H7B	2.1000
O3···H15C^vi	2.6500	H8B···C7	2.9100
O3···H9B	2.8600	H8B···H7B	2.5600
O4···H7B	2.6900	H8C···C9	2.5000
O4···H14C^vii	2.6500	H8C···H9B	1.8100
O4···H7A	2.4900	H9A···O3	2.4500
O4···H9Aⁱⁱⁱ	2.8400	H9A···C10	2.7000
O4···H9Bⁱⁱⁱ	2.9100	H9A···H10A	2.0600
C4···C10ⁱ	3.414 (7)	H9A···O4^viii	2.8400
C4···C11ⁱ	3.567 (7)	H9A···C15^viii	3.0800
C6···C11ⁱ	3.424 (6)	H9B···O3	2.8600
C6···C10ⁱ	3.592 (7)	H9B···C8	2.5200
C7···O3^vii	3.382 (8)	H9B···H8C	1.8100
C9···O4^viii	3.236 (8)	H9B···O4^viii	2.9100
C10···C4ⁱ	3.414 (7)	H10A···O1	2.4200
C10···C6ⁱ	3.592 (7)	H10A···C9	2.3800
C10···O1	3.035 (6)	H10A···C13	2.9000
C11···C4ⁱ	3.567 (7)	H10A···H9A	2.0600
C11···O2	3.295 (6)	H10A···H7Aⁱⁱ	2.4800
C11···C6ⁱ	3.424 (6)	H10B···C4ⁱ	2.9300
C2···H15B^iv	2.9600	H10B···C5ⁱ	2.8200
C4···H11Aⁱ	2.9400	H10B···C10ⁱ	2.9700
C4···H10Bⁱ	2.9300	H10B···H10Bⁱ	2.2700
C5···H11Aⁱ	2.3700	H10B···H11Cⁱⁱ	2.3800
C5···H10Bⁱ	2.8200	H10C···C5ⁱ	2.8100
C5···H10Cⁱ	2.8100	H10C···H14B^ix	2.5000
C6···H11Aⁱ	2.8000	H11A···C4ⁱ	2.9400
C7···H11C	2.8000	H11A···C5ⁱ	2.3700
C7···H8A	2.7700	H11A···C6ⁱ	2.8000
C7···H8B	2.9100	H11B···O2	2.8300
C7···H11B	2.9000	H11B···C7	2.9000
C8···H9B	2.5200	H11C···C7	2.8000
C8···H7B	2.5100	H11C···H7A	2.2000
C9···H10A	2.3800	H11C···C10^vii	3.0600
C9···H8C	2.5000	H11C···H10B^vii	2.3800
C10···H10Bⁱ	2.9700	H14A···O2^iv	2.7600
C10···H11Cⁱⁱ	3.0600	H14B···H10C^x	2.5000
C10···H9A	2.7000	H14C···O4ⁱⁱ	2.6500
C11···H7A	2.6100	H15A···O1^v	2.5800
C13···H10A	2.9000	H15B···C2^v	2.9600
C15···H9Aⁱⁱⁱ	3.0800	H15C···H15C^xi	2.5600
H7A···O4	2.4900	H15C···O3^xii	2.6500

C9—O1—C13	117.3 (4)	C2—C8—H8B	109.00
C7—O2—C12	116.4 (4)	C2—C8—H8C	109.00
C2—C1—C6	119.7 (4)	H8A—C8—H8B	109.00
C2—C1—C7	121.2 (5)	H8A—C8—H8C	109.00
C6—C1—C7	119.1 (4)	H8B—C8—H8C	110.00
C1—C2—C3	120.6 (4)	O1—C9—H9A	110.00
C1—C2—C8	118.3 (5)	O1—C9—H9B	110.00
C3—C2—C8	121.1 (5)	C3—C9—H9A	110.00
C2—C3—C4	119.7 (4)	C3—C9—H9B	110.00
C2—C3—C9	122.2 (4)	H9A—C9—H9B	109.00
C4—C3—C9	118.1 (4)	C4—C10—H10A	109.00
C3—C4—C5	120.4 (4)	C4—C10—H10B	109.00
C3—C4—C10	120.6 (4)	C4—C10—H10C	109.00
C5—C4—C10	118.9 (4)	H10A—C10—H10B	109.00
C4—C5—C6	120.0 (4)	H10A—C10—H10C	110.00
C4—C5—C5ⁱ	120.5 (3)	H10B—C10—H10C	109.00
C5ⁱ—C5—C6	119.4 (4)	C6—C11—H11A	109.00
C1—C6—C5	119.5 (4)	C6—C11—H11B	110.00
C1—C6—C11	121.0 (3)	C6—C11—H11C	109.00
C5—C6—C11	119.5 (4)	H11A—C11—H11B	109.00
O2—C7—C1	108.6 (4)	H11A—C11—H11C	109.00
O1—C9—C3	107.2 (4)	H11B—C11—H11C	110.00
O2—C12—O4	122.5 (5)	C13—C14—H14A	110.00
O2—C12—C15	112.4 (4)	C13—C14—H14B	109.00
O4—C12—C15	125.1 (5)	C13—C14—H14C	109.00
O1—C13—O3	121.7 (5)	H14A—C14—H14B	110.00
O1—C13—C14	113.3 (5)	H14A—C14—H14C	109.00
O3—C13—C14	124.9 (5)	H14B—C14—H14C	109.00
O2—C7—H7A	110.00	C12—C15—H15A	109.00
O2—C7—H7B	110.00	C12—C15—H15B	109.00
C1—C7—H7A	110.00	C12—C15—H15C	109.00
C1—C7—H7B	110.00	H15A—C15—H15B	109.00
H7A—C7—H7B	108.00	H15A—C15—H15C	109.00
C2—C8—H8A	109.00	H15B—C15—H15C	110.00

C13—O1—C9—C3	160.9 (4)	C8—C2—C3—C9	1.5 (8)
C9—O1—C13—O3	2.2 (7)	C2—C3—C4—C5	1.4 (7)
C9—O1—C13—C14	−174.5 (4)	C2—C3—C4—C10	−179.3 (5)
C12—O2—C7—C1	172.3 (4)	C9—C3—C4—C5	−178.5 (4)
C7—O2—C12—O4	−2.1 (8)	C9—C3—C4—C10	0.9 (7)
C7—O2—C12—C15	−180.0 (5)	C2—C3—C9—O1	110.3 (5)
C6—C1—C2—C3	−3.1 (7)	C4—C3—C9—O1	−69.9 (5)
C6—C1—C2—C8	175.7 (5)	C3—C4—C5—C6	−0.4 (6)
C7—C1—C2—C3	174.1 (4)	C3—C4—C5—C5ⁱ	179.2 (4)
C7—C1—C2—C8	−7.1 (7)	C10—C4—C5—C6	−179.7 (4)
C2—C1—C6—C5	4.1 (6)	C10—C4—C5—C5ⁱ	−0.1 (6)
C2—C1—C6—C11	−175.7 (4)	C4—C5—C6—C1	−2.3 (5)
C7—C1—C6—C5	−173.2 (4)	C4—C5—C6—C11	177.4 (4)
C7—C1—C6—C11	7.1 (6)	C5ⁱ—C5—C6—C1	178.1 (3)
C2—C1—C7—O2	98.1 (5)	C5ⁱ—C5—C6—C11	−2.2 (5)
C6—C1—C7—O2	−84.7 (5)	C4—C5—C5ⁱ—C4ⁱ	−83.7 (5)
C1—C2—C3—C4	0.4 (7)	C4—C5—C5ⁱ—C6ⁱ	95.9 (5)
C1—C2—C3—C9	−179.8 (5)	C6—C5—C5ⁱ—C4ⁱ	95.9 (5)
C8—C2—C3—C4	−178.4 (5)	C6—C5—C5ⁱ—C6ⁱ	−84.5 (4)

Symmetry codes: (i) −x+1, −y, z; (ii) −x+1, y, z−1/2; (iii) −x+1/2, −y+1/2, z+1/2; (iv) x+1/2, −y+1/2, z; (v) x−1/2, −y+1/2, z; (vi) x+1/2, y+1/2, z−1/2; (vii) −x+1, y, z+1/2; (viii) −x+1/2, −y+1/2, z−1/2; (ix) −x+3/2, y−1/2, z; (x) −x+3/2, y+1/2, z; (xi) −x, −y, z; (xii) x−1/2, y−1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1	0.96	2.42	3.035 (6)	122
C15—H15A···O1^v	0.96	2.58	3.472 (7)	155

Symmetry code: (v) x−1/2, −y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₃₀H₃₈O₈
M_r	526.60
Crystal system, space group	Orthorhombic, Iba2
Temperature (K)	293
a, b, c (Å)	15.336 (2), 12.658 (1), 14.755 (2)
V (Å³)	2864.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.983, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	8052, 1709, 1045
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.199, 1.02
No. of reflections	1709
No. of parameters	173
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.14

Computer programs: SMART (Bruker, 2007), SAINT-Plus (Bruker, 2007), 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
C15—H15A···O1ⁱ	0.9600	2.5800	3.472 (7)	155.00

Symmetry code: (i) x−1/2, −y+1/2, z.

Acknowledgements

The author is grateful for funding support from the Natural Science Foundation of Shanxi Province (grant No. 2007011033), the Program for Technological Industrialization at the University of Shanxi Province (grant No. 20070308) and the start-up fund of the North University of China.

References

Bruker (2007). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Frohlich, R. & Musso, H. (1985). Chem. Ber. 118, 4649–4651. CrossRef Web of Science Google Scholar
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Natarajan, R., Savitha, G., Dominiak, P., Wozniak, K. & Moorthy, J. N. (2005a). Angew. Chem. Int. Ed. 44, 2115–2119. Web of Science CSD CrossRef CAS Google Scholar
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Volume 65| Part 6| June 2009| Page o1355

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,2′,4,4′,6,6′-Hexa­methyl­bi­phenyl-3,3′,5,5′-tetra­yltetra­methyl­ene tetra­acetate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,2′,4,4′,6,6′-Hexamethylbiphenyl-3,3′,5,5′-tetrayltetramethylene tetraacetate