2,6-Di-tert-butyl-4-(methoxy­meth­yl)phenol

Zeng, T.; Sun, J.-F.

doi:10.1107/S1600536808003644

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o588

doi:10.1107/S1600536808003644

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2,6-Di-tert-butyl-4-(methoxymethyl)phenol

Tao Zeng ^a ^* and Ju-Feng Sun ^b

^aChemistry & Biology College, Ynatai University, Yantai 264005, People's Republic of China, and ^bBinzhou Medical University, Yantai 264003, People's Republic of China
^*Correspondence e-mail: zengtaotj@126.com

(Received 15 November 2007; accepted 1 February 2008; online 13 February 2008)

The title compound, C₁₆H₂₆O₂, was easily obtained in high yield when 4-bromomethyl-2,6-di-tert-butylphenol was reacted with methanol. There are two independent molecules in the asymmetric unit. The methoxy group in each of the independent molecules was found to be disordered, with site-occupation factors of 0.8728 (18)/0.1272 (18) and 0.8781 (17)/0.1219 (17).

Related literature

For related literature, see: Rieker et al. (1968 ); Yamazaki & Seguchi (1997 ); Zeng et al. (2005 ).

Experimental

Crystal data

C₁₆H₂₆O₂
M_r = 250.37
Monoclinic, P 2₁ /c
a = 14.240 (3) Å
b = 18.012 (3) Å
c = 13.677 (3) Å
β = 118.603 (3)°
V = 3079.7 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 294 (2) K
0.26 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ) T_min = 0.982, T_max = 0.986
15799 measured reflections
5428 independent reflections
2928 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.189
S = 1.04
5428 reflections
378 parameters
108 restraints
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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 I, global. DOI: 10.1107/S1600536808003644/er2048sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003644/er2048Isup2.hkl

checkCIF report

Comment top

Hindered phenol antioxidants are widely used in polymers and lubricants. It could protect polymers by increasing both their process stability and long-term stability against oxidative degradation (Yamazaki & Seguchi, 1997). In former papers, we have reported the reaction of 4-bromomethyl-20,6-di-tet-butyl-phenol with amines (Zeng et al., 2005) and it was showed that the 4-bromomethyl-2,6-di-tet-butyl-phenol was highly reactive. The title compound, C₁₆H₂₆O₂,(1),has been easily synthesied when we tried to dissolve the 4-bromomethyl-2,6-di-tert-butyl-phenol in methanol. It was found that there are two independent molecules in the asymmetric units. The phenolic hydroxyl are hindered by the adjacent tert-butyl groups. And both of the methoxyl groups in the two molecules were found disordered with with site occupation fators 0.8728 (18)/0.1272 (18) and 0.8781 (17)/0.1219 (17).

Related literature top

For related literature, see: Rieker et al. (1968); Yamazaki & Seguchi (1997); Zeng et al. (2005).

Experimental top

The 4-bromomethyl-2,6-di-tert-butyl-phenol (7.15 g) was synthesized from 2,6-di-tert-butyl-4-methylphenol (5.5 g, 0.025 mol) and equivalent NBS (Rieker et al., 1968) in a yield of 96%. Then 40 ml me thanol was added and stirred for 5 min the produt (5.85 g, 0.023 mol) was obtained in a yield of 97.3%. Suitable crystals were obtained by slow evaporation of a mixture of ethyl acetate and ethanol.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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. The two independent molecules in the structure of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

2,6-di-tert-butyl-4-(methoxymethyl)phenol top

Crystal data top

C₁₆H₂₆O₂	F(000) = 1104
M_r = 250.37	D_x = 1.080 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.240 (3) Å	Cell parameters from 2933 reflections
b = 18.012 (3) Å	θ = 2.8–25.4°
c = 13.677 (3) Å	µ = 0.07 mm⁻¹
β = 118.603 (3)°	T = 294 K
V = 3079.7 (10) Å³	Block, colourless
Z = 8	0.26 × 0.24 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	5428 independent reflections
Radiation source: fine-focus sealed tube	2928 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −13→16
T_min = 0.982, T_max = 0.986	k = −20→21
15799 measured reflections	l = −16→10

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)] = 0.060	H-atom parameters constrained
wR(F²) = 0.189	w = 1/[σ²(F_o²) + (0.0751P)² + 1.0963P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.002
5428 reflections	Δρ_max = 0.31 e Å⁻³
378 parameters	Δρ_min = −0.26 e Å⁻³
108 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: 0.0102 (7)

Crystal data top

C₁₆H₂₆O₂	V = 3079.7 (10) Å³
M_r = 250.37	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.240 (3) Å	µ = 0.07 mm⁻¹
b = 18.012 (3) Å	T = 294 K
c = 13.677 (3) Å	0.26 × 0.24 × 0.20 mm
β = 118.603 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5428 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	2928 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.986	R_int = 0.046
15799 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	108 restraints
wR(F²) = 0.189	H-atom parameters constrained
S = 1.04	Δρ_max = 0.31 e Å⁻³
5428 reflections	Δρ_min = −0.26 e Å⁻³
378 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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	Occ. (<1)
O1	0.29438 (11)	0.73376 (8)	0.66027 (11)	0.0698 (5)
H1	0.2550	0.7700	0.6367	0.105*
O3	0.20663 (10)	0.25936 (8)	0.37111 (12)	0.0701 (4)
H3	0.2381	0.2196	0.3821	0.105*
C1	0.35866 (12)	0.74063 (10)	0.77320 (14)	0.0425 (5)
C2	0.39601 (12)	0.67334 (9)	0.83200 (14)	0.0410 (5)
C3	0.46179 (12)	0.67844 (10)	0.94611 (14)	0.0448 (5)
H3A	0.4869	0.6349	0.9871	0.054*
C4	0.49145 (12)	0.74549 (10)	1.00116 (14)	0.0453 (5)
C5	0.45463 (13)	0.80952 (10)	0.94014 (15)	0.0501 (5)
H5	0.4756	0.8548	0.9771	0.060*
C6	0.38758 (12)	0.80988 (10)	0.82580 (15)	0.0450 (5)
C7	0.34673 (15)	0.88356 (11)	0.76197 (18)	0.0626 (6)
C8	0.22446 (17)	0.88849 (13)	0.7136 (2)	0.0880 (9)
H8A	0.1995	0.9353	0.6763	0.132*
H8B	0.2067	0.8845	0.7728	0.132*
H8C	0.1910	0.8488	0.6614	0.132*
C9	0.3953 (2)	0.95088 (12)	0.8398 (2)	0.0973 (10)
H9A	0.4714	0.9513	0.8684	0.146*
H9B	0.3796	0.9474	0.9006	0.146*
H9C	0.3651	0.9958	0.7990	0.146*
C10	0.37776 (19)	0.89054 (13)	0.6695 (2)	0.0911 (8)
H10A	0.3479	0.9354	0.6282	0.137*
H10B	0.3506	0.8486	0.6205	0.137*
H10C	0.4543	0.8920	0.7020	0.137*
C11	0.36507 (14)	0.59799 (10)	0.77160 (16)	0.0528 (6)
C12	0.40573 (18)	0.59247 (12)	0.68675 (19)	0.0808 (8)
H12A	0.3708	0.6292	0.6298	0.121*
H12B	0.3904	0.5439	0.6537	0.121*
H12C	0.4816	0.6008	0.7234	0.121*
C13	0.41538 (18)	0.53359 (11)	0.8551 (2)	0.0815 (9)
H13A	0.3971	0.4872	0.8157	0.122*
H13B	0.3886	0.5343	0.9076	0.122*
H13C	0.4917	0.5392	0.8940	0.122*
C14	0.24411 (16)	0.58545 (12)	0.7145 (2)	0.0785 (8)
H14A	0.2089	0.6230	0.6588	0.118*
H14B	0.2197	0.5881	0.7688	0.118*
H14C	0.2277	0.5374	0.6800	0.118*
C17	0.14067 (12)	0.25795 (10)	0.41872 (14)	0.0428 (5)
C18	0.11153 (12)	0.19114 (9)	0.44964 (14)	0.0424 (5)
C19	0.04478 (13)	0.19708 (10)	0.49784 (14)	0.0473 (5)
H19	0.0243	0.1539	0.5200	0.057*
C20	0.00815 (12)	0.26412 (10)	0.51383 (14)	0.0463 (5)
C21	0.03681 (13)	0.32793 (10)	0.47987 (14)	0.0469 (5)
H21	0.0107	0.3731	0.4894	0.056*
C22	0.10338 (13)	0.32747 (10)	0.43179 (14)	0.0435 (5)
C23	0.13593 (15)	0.40024 (10)	0.39658 (16)	0.0565 (6)
C24	0.25658 (16)	0.41172 (13)	0.4620 (2)	0.0821 (8)
H24A	0.2748	0.4583	0.4412	0.123*
H24B	0.2920	0.3721	0.4456	0.123*
H24C	0.2789	0.4120	0.5402	0.123*
C25	0.0990 (2)	0.39898 (13)	0.27121 (18)	0.0843 (8)
H25A	0.1168	0.4453	0.2495	0.126*
H25B	0.0230	0.3916	0.2308	0.126*
H25C	0.1342	0.3592	0.2549	0.126*
C26	0.08391 (18)	0.46798 (11)	0.4192 (2)	0.0839 (8)
H26A	0.1046	0.4700	0.4971	0.126*
H26B	0.0075	0.4639	0.3766	0.126*
H26C	0.1071	0.5124	0.3982	0.126*
C27	0.15203 (15)	0.11556 (11)	0.43482 (17)	0.0591 (6)
C28	0.12020 (19)	0.10122 (12)	0.3133 (2)	0.0873 (8)
H28A	0.0437	0.1021	0.2696	0.131*
H28B	0.1465	0.0535	0.3064	0.131*
H28C	0.1503	0.1390	0.2872	0.131*
C29	0.10241 (17)	0.05158 (11)	0.4707 (2)	0.0827 (8)
H29A	0.1247	0.0559	0.5487	0.124*
H29B	0.1260	0.0048	0.4566	0.124*
H29C	0.0258	0.0544	0.4290	0.124*
C30	0.27315 (16)	0.11003 (13)	0.5082 (2)	0.0907 (9)
H30A	0.3074	0.1487	0.4885	0.136*
H30B	0.2974	0.0626	0.4973	0.136*
H30C	0.2907	0.1153	0.5849	0.136*
C15	0.55793 (15)	0.75095 (12)	1.12630 (15)	0.0648 (6)	0.8728 (18)
H15A	0.5955	0.7980	1.1459	0.078*	0.8728 (18)
H15B	0.5114	0.7492	1.1598	0.078*	0.8728 (18)
O2	0.63105 (11)	0.69353 (9)	1.16775 (11)	0.0614 (5)	0.8728 (18)
C16	0.6887 (2)	0.69504 (18)	1.28628 (18)	0.0875 (10)	0.8728 (18)
H16A	0.7390	0.6548	1.3127	0.131*	0.8728 (18)
H16B	0.6397	0.6901	1.3155	0.131*	0.8728 (18)
H16C	0.7264	0.7413	1.3106	0.131*	0.8728 (18)
C15'	0.5580 (8)	0.7510 (7)	1.1264 (5)	0.0648 (6)	0.1272 (18)
H15C	0.5102	0.7640	1.1557	0.078*	0.1272 (18)
H15D	0.5856	0.7018	1.1541	0.078*	0.1272 (18)
O2'	0.6430 (6)	0.7997 (6)	1.1711 (6)	0.105 (6)	0.1272 (18)
C16'	0.6844 (13)	0.7853 (10)	1.2889 (7)	0.073 (5)	0.1272 (18)
H16D	0.7463	0.8156	1.3310	0.110*	0.1272 (18)
H16E	0.7037	0.7339	1.3040	0.110*	0.1272 (18)
H16F	0.6306	0.7969	1.3097	0.110*	0.1272 (18)
C31	−0.0573 (9)	0.2684 (4)	0.5737 (4)	0.0646 (6)	0.8781 (17)
H31A	−0.0098	0.2663	0.6533	0.078*	0.8781 (17)
H31B	−0.0948	0.3154	0.5568	0.078*	0.8781 (17)
O4	−0.13064 (10)	0.21107 (9)	0.54314 (11)	0.0608 (5)	0.8781 (17)
C32	−0.18536 (18)	0.21175 (19)	0.6076 (2)	0.0943 (11)	0.8781 (17)
H32A	−0.2358	0.1716	0.5845	0.141*	0.8781 (17)
H32B	−0.2226	0.2580	0.5966	0.141*	0.8781 (17)
H32C	−0.1345	0.2061	0.6850	0.141*	0.8781 (17)
C31'	−0.0573 (9)	0.2684 (4)	0.5737 (4)	0.0646 (6)	0.1219 (17)
H31C	−0.0839	0.2190	0.5752	0.078*	0.1219 (17)
H31D	−0.0106	0.2831	0.6501	0.078*	0.1219 (17)
O4'	−0.1426 (5)	0.3164 (5)	0.5280 (6)	0.071 (3)	0.1219 (17)
C32'	−0.1973 (8)	0.3038 (9)	0.5923 (9)	0.060 (4)	0.1219 (17)
H32D	−0.2571	0.3371	0.5676	0.089*	0.1219 (17)
H32E	−0.1489	0.3125	0.6697	0.089*	0.1219 (17)
H32F	−0.2224	0.2535	0.5823	0.089*	0.1219 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0750 (9)	0.0690 (9)	0.0423 (8)	0.0148 (7)	0.0095 (7)	0.0070 (7)
O3	0.0796 (7)	0.0652 (9)	0.0971 (8)	0.0051 (7)	0.0677 (6)	0.0076 (7)
C1	0.0349 (8)	0.0530 (10)	0.0384 (9)	0.0040 (8)	0.0167 (7)	0.0026 (8)
C2	0.0342 (8)	0.0445 (10)	0.0426 (9)	0.0019 (7)	0.0171 (7)	0.0041 (8)
C3	0.0345 (8)	0.0532 (10)	0.0451 (9)	0.0028 (8)	0.0178 (7)	0.0099 (8)
C4	0.0330 (8)	0.0600 (11)	0.0424 (9)	−0.0013 (8)	0.0177 (7)	−0.0034 (9)
C5	0.0427 (8)	0.0513 (11)	0.0595 (10)	−0.0009 (8)	0.0272 (8)	−0.0114 (9)
C6	0.0379 (8)	0.0463 (10)	0.0548 (10)	0.0044 (8)	0.0255 (7)	0.0010 (8)
C7	0.0625 (11)	0.0460 (11)	0.0771 (13)	0.0114 (9)	0.0318 (10)	0.0058 (10)
C8	0.0754 (13)	0.0737 (15)	0.1056 (18)	0.0319 (12)	0.0358 (13)	0.0151 (13)
C9	0.1047 (17)	0.0478 (13)	0.126 (2)	0.0059 (13)	0.0441 (15)	−0.0020 (14)
C10	0.1118 (16)	0.0688 (14)	0.1058 (16)	0.0121 (13)	0.0626 (13)	0.0317 (13)
C11	0.0470 (9)	0.0475 (11)	0.0550 (11)	−0.0020 (8)	0.0172 (8)	0.0005 (9)
C12	0.0961 (14)	0.0655 (14)	0.0892 (15)	−0.0035 (12)	0.0511 (12)	−0.0236 (12)
C13	0.0829 (15)	0.0466 (12)	0.0873 (17)	−0.0029 (11)	0.0184 (13)	0.0079 (12)
C14	0.0588 (12)	0.0702 (14)	0.0853 (16)	−0.0185 (11)	0.0174 (12)	−0.0097 (12)
C17	0.0356 (7)	0.0538 (11)	0.0412 (9)	−0.0024 (8)	0.0201 (7)	0.0017 (8)
C18	0.0352 (8)	0.0455 (10)	0.0433 (9)	0.0007 (8)	0.0163 (7)	0.0050 (8)
C19	0.0380 (8)	0.0542 (11)	0.0494 (10)	−0.0012 (8)	0.0206 (7)	0.0113 (9)
C20	0.0346 (8)	0.0618 (11)	0.0409 (9)	0.0026 (8)	0.0167 (7)	0.0020 (9)
C21	0.0399 (8)	0.0511 (10)	0.0457 (10)	0.0012 (8)	0.0172 (7)	−0.0046 (9)
C22	0.0393 (8)	0.0464 (10)	0.0408 (9)	−0.0026 (8)	0.0158 (7)	0.0003 (8)
C23	0.0612 (10)	0.0472 (11)	0.0587 (11)	−0.0110 (9)	0.0269 (9)	−0.0012 (9)
C24	0.0755 (12)	0.0713 (14)	0.0990 (16)	−0.0283 (11)	0.0415 (12)	−0.0053 (13)
C25	0.1207 (16)	0.0698 (14)	0.0628 (13)	−0.0133 (13)	0.0443 (12)	0.0119 (11)
C26	0.1037 (15)	0.0477 (12)	0.1044 (17)	−0.0043 (12)	0.0532 (13)	−0.0026 (12)
C27	0.0565 (9)	0.0487 (11)	0.0801 (12)	0.0080 (9)	0.0392 (9)	0.0096 (10)
C28	0.1188 (16)	0.0573 (13)	0.0998 (16)	0.0070 (13)	0.0637 (13)	−0.0119 (12)
C29	0.0912 (13)	0.0477 (12)	0.1248 (17)	0.0076 (11)	0.0643 (12)	0.0154 (12)
C30	0.0632 (12)	0.0791 (15)	0.133 (2)	0.0299 (11)	0.0492 (12)	0.0286 (14)
C15	0.0585 (10)	0.0878 (15)	0.0508 (10)	0.0038 (10)	0.0283 (8)	−0.0017 (10)
O2	0.0523 (8)	0.0869 (11)	0.0372 (8)	0.0066 (8)	0.0153 (6)	0.0022 (8)
C16	0.0718 (16)	0.142 (3)	0.0366 (13)	0.0054 (17)	0.0159 (12)	0.0100 (15)
C15'	0.0585 (10)	0.0878 (15)	0.0508 (10)	0.0038 (10)	0.0283 (8)	−0.0017 (10)
O2'	0.043 (6)	0.204 (15)	0.049 (7)	0.037 (8)	0.006 (5)	−0.019 (8)
C16'	0.069 (6)	0.087 (7)	0.061 (6)	−0.005 (6)	0.029 (5)	−0.002 (6)
C31	0.0554 (9)	0.0890 (14)	0.0601 (10)	−0.0009 (10)	0.0362 (8)	0.0004 (10)
O4	0.0464 (7)	0.0904 (11)	0.0556 (8)	−0.0017 (8)	0.0326 (6)	0.0079 (8)
C32	0.0657 (12)	0.163 (3)	0.0771 (15)	−0.0018 (17)	0.0522 (11)	0.0131 (17)
C31'	0.0554 (9)	0.0890 (14)	0.0601 (10)	−0.0009 (10)	0.0362 (8)	0.0004 (10)
O4'	0.065 (4)	0.091 (4)	0.065 (4)	0.001 (3)	0.038 (3)	−0.001 (4)
C32'	0.061 (6)	0.073 (7)	0.066 (6)	0.012 (5)	0.048 (4)	0.001 (5)

Geometric parameters (Å, º) top

O1—C1	1.373 (2)	C21—H21	0.9300
O1—H1	0.8200	C22—C23	1.542 (3)
O3—C17	1.376 (2)	C23—C24	1.524 (3)
O3—H3	0.8200	C23—C26	1.534 (3)
C1—C6	1.400 (2)	C23—C25	1.534 (3)
C1—C2	1.410 (2)	C24—H24A	0.9600
C2—C3	1.386 (2)	C24—H24B	0.9600
C2—C11	1.539 (2)	C24—H24C	0.9600
C3—C4	1.378 (2)	C25—H25A	0.9600
C3—H3A	0.9300	C25—H25B	0.9600
C4—C5	1.372 (2)	C25—H25C	0.9600
C4—C15	1.511 (2)	C26—H26A	0.9600
C5—C6	1.388 (2)	C26—H26B	0.9600
C5—H5	0.9300	C26—H26C	0.9600
C6—C7	1.541 (3)	C27—C28	1.521 (3)
C7—C10	1.531 (4)	C27—C30	1.528 (3)
C7—C8	1.541 (3)	C27—C29	1.549 (3)
C7—C9	1.542 (3)	C28—H28A	0.9600
C8—H8A	0.9600	C28—H28B	0.9600
C8—H8B	0.9600	C28—H28C	0.9600
C8—H8C	0.9600	C29—H29A	0.9600
C9—H9A	0.9600	C29—H29B	0.9600
C9—H9B	0.9600	C29—H29C	0.9600
C9—H9C	0.9600	C30—H30A	0.9600
C10—H10A	0.9600	C30—H30B	0.9600
C10—H10B	0.9600	C30—H30C	0.9600
C10—H10C	0.9600	C15—O2	1.382 (2)
C11—C12	1.528 (3)	C15—H15A	0.9700
C11—C14	1.530 (3)	C15—H15B	0.9700
C11—C13	1.543 (3)	O2—C16	1.424 (3)
C12—H12A	0.9600	C16—H16A	0.9600
C12—H12B	0.9600	C16—H16B	0.9600
C12—H12C	0.9600	C16—H16C	0.9600
C13—H13A	0.9600	O2'—C16'	1.449 (8)
C13—H13B	0.9600	C16'—H16D	0.9600
C13—H13C	0.9600	C16'—H16E	0.9600
C14—H14A	0.9600	C16'—H16F	0.9600
C14—H14B	0.9600	C31—O4	1.383 (2)
C14—H14C	0.9600	C31—H31A	0.9700
C17—C18	1.403 (2)	C31—H31B	0.9700
C17—C22	1.404 (2)	O4—C32	1.429 (3)
C18—C19	1.396 (3)	C32—H32A	0.9600
C18—C27	1.529 (3)	C32—H32B	0.9600
C19—C20	1.374 (3)	C32—H32C	0.9600
C19—H19	0.9300	O4'—C32'	1.445 (9)
C20—C21	1.373 (3)	C32'—H32D	0.9600
C20—C31	1.507 (3)	C32'—H32E	0.9600
C21—C22	1.389 (3)	C32'—H32F	0.9600

C1—O1—H1	109.5	C24—C23—C26	106.94 (17)
C17—O3—H3	109.5	C24—C23—C25	110.1 (2)
O1—C1—C6	122.15 (15)	C26—C23—C25	107.30 (17)
O1—C1—C2	115.50 (15)	C24—C23—C22	110.80 (15)
C6—C1—C2	122.33 (15)	C26—C23—C22	111.50 (19)
C3—C2—C1	116.88 (16)	C25—C23—C22	110.07 (15)
C3—C2—C11	121.88 (15)	C23—C24—H24A	109.5
C1—C2—C11	121.24 (15)	C23—C24—H24B	109.5
C4—C3—C2	122.57 (16)	H24A—C24—H24B	109.5
C4—C3—H3A	118.7	C23—C24—H24C	109.5
C2—C3—H3A	118.7	H24A—C24—H24C	109.5
C5—C4—C3	118.45 (15)	H24B—C24—H24C	109.5
C5—C4—C15	118.95 (17)	C23—C25—H25A	109.5
C3—C4—C15	122.52 (17)	C23—C25—H25B	109.5
C4—C5—C6	123.06 (17)	H25A—C25—H25B	109.5
C4—C5—H5	118.5	C23—C25—H25C	109.5
C6—C5—H5	118.5	H25A—C25—H25C	109.5
C5—C6—C1	116.70 (16)	H25B—C25—H25C	109.5
C5—C6—C7	120.77 (16)	C23—C26—H26A	109.5
C1—C6—C7	122.53 (16)	C23—C26—H26B	109.5
C10—C7—C8	110.73 (19)	H26A—C26—H26B	109.5
C10—C7—C6	111.01 (18)	C23—C26—H26C	109.5
C8—C7—C6	109.59 (17)	H26A—C26—H26C	109.5
C10—C7—C9	107.1 (2)	H26B—C26—H26C	109.5
C8—C7—C9	107.01 (19)	C28—C27—C30	111.0 (2)
C6—C7—C9	111.29 (17)	C28—C27—C18	111.22 (16)
C7—C8—H8A	109.5	C30—C27—C18	110.47 (16)
C7—C8—H8B	109.5	C28—C27—C29	106.11 (18)
H8A—C8—H8B	109.5	C30—C27—C29	106.62 (17)
C7—C8—H8C	109.5	C18—C27—C29	111.22 (18)
H8A—C8—H8C	109.5	C27—C28—H28A	109.5
H8B—C8—H8C	109.5	C27—C28—H28B	109.5
C7—C9—H9A	109.5	H28A—C28—H28B	109.5
C7—C9—H9B	109.5	C27—C28—H28C	109.5
H9A—C9—H9B	109.5	H28A—C28—H28C	109.5
C7—C9—H9C	109.5	H28B—C28—H28C	109.5
H9A—C9—H9C	109.5	C27—C29—H29A	109.5
H9B—C9—H9C	109.5	C27—C29—H29B	109.5
C7—C10—H10A	109.5	H29A—C29—H29B	109.5
C7—C10—H10B	109.5	C27—C29—H29C	109.5
H10A—C10—H10B	109.5	H29A—C29—H29C	109.5
C7—C10—H10C	109.5	H29B—C29—H29C	109.5
H10A—C10—H10C	109.5	C27—C30—H30A	109.5
H10B—C10—H10C	109.5	C27—C30—H30B	109.5
C12—C11—C14	110.25 (18)	H30A—C30—H30B	109.5
C12—C11—C2	110.47 (17)	C27—C30—H30C	109.5
C14—C11—C2	111.54 (16)	H30A—C30—H30C	109.5
C12—C11—C13	107.62 (18)	H30B—C30—H30C	109.5
C14—C11—C13	106.10 (17)	O2—C15—C4	110.88 (17)
C2—C11—C13	110.70 (15)	O2—C15—H15A	109.5
C11—C12—H12A	109.5	C4—C15—H15A	109.5
C11—C12—H12B	109.5	O2—C15—H15B	109.5
H12A—C12—H12B	109.5	C4—C15—H15B	109.5
C11—C12—H12C	109.5	H15A—C15—H15B	108.1
H12A—C12—H12C	109.5	C15—O2—C16	111.31 (19)
H12B—C12—H12C	109.5	O2—C16—H16A	109.5
C11—C13—H13A	109.5	O2—C16—H16B	109.5
C11—C13—H13B	109.5	H16A—C16—H16B	109.5
H13A—C13—H13B	109.5	O2—C16—H16C	109.5
C11—C13—H13C	109.5	H16A—C16—H16C	109.5
H13A—C13—H13C	109.5	H16B—C16—H16C	109.5
H13B—C13—H13C	109.5	O2'—C16'—H16D	109.5
C11—C14—H14A	109.5	O2'—C16'—H16E	109.5
C11—C14—H14B	109.5	H16D—C16'—H16E	109.5
H14A—C14—H14B	109.5	O2'—C16'—H16F	109.5
C11—C14—H14C	109.5	H16D—C16'—H16F	109.5
H14A—C14—H14C	109.5	H16E—C16'—H16F	109.5
H14B—C14—H14C	109.5	O4—C31—C20	111.93 (17)
O3—C17—C18	121.74 (16)	O4—C31—H31A	109.2
O3—C17—C22	115.43 (16)	C20—C31—H31A	109.2
C18—C17—C22	122.82 (18)	O4—C31—H31B	109.2
C19—C18—C17	116.31 (16)	C20—C31—H31B	109.2
C19—C18—C27	121.06 (17)	H31A—C31—H31B	107.9
C17—C18—C27	122.61 (18)	C31—O4—C32	111.38 (19)
C20—C19—C18	122.59 (17)	O4—C32—H32A	109.5
C20—C19—H19	118.7	O4—C32—H32B	109.5
C18—C19—H19	118.7	H32A—C32—H32B	109.5
C21—C20—C19	119.02 (18)	O4—C32—H32C	109.5
C21—C20—C31	120.16 (18)	H32A—C32—H32C	109.5
C19—C20—C31	120.73 (18)	H32B—C32—H32C	109.5
C20—C21—C22	122.41 (17)	O4'—C32'—H32D	109.5
C20—C21—H21	118.8	O4'—C32'—H32E	109.5
C22—C21—H21	118.8	H32D—C32'—H32E	109.5
C21—C22—C17	116.82 (17)	O4'—C32'—H32F	109.5
C21—C22—C23	121.21 (17)	H32D—C32'—H32F	109.5
C17—C22—C23	121.97 (18)	H32E—C32'—H32F	109.5

O1—C1—C2—C3	179.52 (16)	C22—C17—C18—C27	179.76 (15)
C6—C1—C2—C3	1.3 (3)	C17—C18—C19—C20	0.5 (2)
O1—C1—C2—C11	−0.3 (3)	C27—C18—C19—C20	179.07 (15)
C6—C1—C2—C11	−178.52 (18)	C18—C19—C20—C21	0.9 (2)
C1—C2—C3—C4	−0.8 (3)	C18—C19—C20—C31	−175.59 (15)
C11—C2—C3—C4	179.05 (18)	C19—C20—C21—C22	−1.3 (2)
C2—C3—C4—C5	−0.3 (3)	C31—C20—C21—C22	175.23 (15)
C2—C3—C4—C15	176.40 (18)	C20—C21—C22—C17	0.2 (2)
C3—C4—C5—C6	1.0 (3)	C20—C21—C22—C23	−178.79 (15)
C15—C4—C5—C6	−175.84 (18)	O3—C17—C22—C21	−179.85 (14)
C4—C5—C6—C1	−0.5 (3)	C18—C17—C22—C21	1.4 (2)
C4—C5—C6—C7	178.64 (19)	O3—C17—C22—C23	−0.9 (2)
O1—C1—C6—C5	−178.78 (17)	C18—C17—C22—C23	−179.64 (15)
C2—C1—C6—C5	−0.7 (3)	C21—C22—C23—C24	117.6 (2)
O1—C1—C6—C7	2.1 (3)	C17—C22—C23—C24	−61.3 (2)
C2—C1—C6—C7	−179.83 (18)	C21—C22—C23—C26	−1.4 (2)
C5—C6—C7—C10	122.6 (2)	C17—C22—C23—C26	179.73 (15)
C1—C6—C7—C10	−58.3 (2)	C21—C22—C23—C25	−120.32 (19)
C5—C6—C7—C8	−114.8 (2)	C17—C22—C23—C25	60.8 (2)
C1—C6—C7—C8	64.4 (3)	C19—C18—C27—C28	122.42 (19)
C5—C6—C7—C9	3.4 (3)	C17—C18—C27—C28	−59.2 (2)
C1—C6—C7—C9	−177.5 (2)	C19—C18—C27—C30	−113.8 (2)
C3—C2—C11—C12	−118.3 (2)	C17—C18—C27—C30	64.6 (2)
C1—C2—C11—C12	61.5 (2)	C19—C18—C27—C29	4.4 (2)
C3—C2—C11—C14	118.7 (2)	C17—C18—C27—C29	−177.19 (16)
C1—C2—C11—C14	−61.5 (3)	C5—C4—C15—O2	−148.81 (18)
C3—C2—C11—C13	0.8 (3)	C3—C4—C15—O2	34.4 (3)
C1—C2—C11—C13	−179.37 (19)	C4—C15—O2—C16	−175.74 (19)
O3—C17—C18—C19	179.58 (14)	C21—C20—C31—O4	142.81 (16)
C22—C17—C18—C19	−1.7 (2)	C19—C20—C31—O4	−40.7 (2)
O3—C17—C18—C27	1.1 (2)	C20—C31—O4—C32	174.72 (17)

Experimental details

Crystal data
Chemical formula	C₁₆H₂₆O₂
M_r	250.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	14.240 (3), 18.012 (3), 13.677 (3)
β (°)	118.603 (3)
V (Å³)	3079.7 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.26 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2002)
T_min, T_max	0.982, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	15799, 5428, 2928
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.189, 1.04
No. of reflections	5428
No. of parameters	378
No. of restraints	108
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.26

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors gratefully acknowledge financial support from the Start Foundation for Doctors (HY071314) of Yantai University.

References

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Rieker, A., Kaufmann, D., Brück, R., Workman, R. & Müller, E. (1968). Tetrahedron, 24, 103–115. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yamazaki, T. & Seguchi, T. (1997). J. Polym. Sci. A: Polym. Chem. 35, 2431–2439. Google Scholar
Zeng, T., Dong, C.-M. & Shu, X.-G. (2005). Acta Cryst. E61, o2334–o2335. CSD CrossRef CAS IUCr Journals Google Scholar