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COMMUNICATIONS
ISSN: 2056-9890

3,3′,5,5′-Tetra-tert-butyl-2′-hy­dr­oxy-[1,1′-biphen­yl]-2-yl 4-methyl­benzene­sulfonate

aDepartment of Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China
*Correspondence e-mail: wujc@lzu.edu.cn

(Received 21 December 2012; accepted 27 December 2012; online 4 January 2013)

In the title mol­ecule, C37H48O4S, the benzene rings in the biphenyl fragment are inclined to each other at 61.1 (1)°. The hy­droxy group is involved in a weak intra­molecular O—H⋯Osulfonate hydrogen bond. One tert-butyl group is disodered over two orientations in a 0.682 (17):0.318 (17) ratio. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into columns in direction [100].

Related literature

For applications of coordination complexes with close ligands in the ring-opening polymerization of cyclic esters, see: Wu et al. (2006[Wu, J., Yu, T.-L., Chen, C.-T. & Lin, C.-C. (2006). Coord. Chem. Rev. 250, 602-626.]). For the crystal structures of related compounds, see: Wu et al. (2009[Wu, J., Pan, X., Wang, L. & Yao, L. (2009). Acta Cryst. E65, o155.]); Wang & Wu (2012[Wang, C. & Wu, J. (2012). Acta Cryst. E68, o93.]).

[Scheme 1]

Experimental

Crystal data
  • C35H48O4S

  • Mr = 564.79

  • Triclinic, [P \overline 1]

  • a = 9.885 (2) Å

  • b = 12.948 (3) Å

  • c = 13.600 (3) Å

  • α = 101.761 (2)°

  • β = 102.539 (2)°

  • γ = 92.004 (2)°

  • V = 1657.8 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.13 mm−1

  • T = 296 K

  • 0.28 × 0.22 × 0.21 mm

Data collection
  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004)[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.] Tmin = 0.965, Tmax = 0.973

  • 11516 measured reflections

  • 7609 independent reflections

  • 3453 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.074

  • wR(F2) = 0.205

  • S = 0.99

  • 7609 reflections

  • 389 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2A⋯O4 0.82 2.59 3.322 (4) 149
C24—H24C⋯O3i 0.96 2.67 3.372 (4) 130
C25—H25C⋯O4ii 0.96 2.64 3.500 (4) 150
C20—H20B⋯O3ii 0.96 2.69 3.609 (5) 160
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Polyesters as potentially valuable "green plastics" are attracting increasing attention. Many coordination complexes have been designed and synthesized as initiators or catalysts for the ring-opening polymerization of cyclic esters (Wu et al., 2006). Herewith we present the title compound (I).

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related compounds (Wu et al., 2009; Wang et al., 2012). Two benzene rings in the biphenyl fragment are inclined to each other at 61.1 (1)°. The hydroxy group is involved in a weak intramolecular O2—H2A···O4 hydrogen bond (Table 1). In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into columns in [100].

Related literature top

For applications of coordination complexes with close ligands in the ring-opening polymerization of cyclic esters, see: Wu et al. (2006). For the crystal structures of related compounds, see: Wu et al. (2009); Wang & Wu (2012).

Experimental top

This title compound was synthesized by condensation of 3,3',5,5'-tetra-tert-butyl-[1,1'-biphenyl]-2,2'-diol and and 4- methylbenzene-1-sulfonyl chloride in dichloromethane at 0°C for about 1 h in the presence of 10 equiv. triethylamine. The crystals were obtained by slow cooling a hexane solution.

Refinement top

C-bound H atoms were geometrically positioned, and were treated as riding on their parent atoms, with C—H= 0.93–0.96 Å and Uiso(H) = 1.2-1.5 Ueq(C). The O-bound H atom was located in a difference Fourier map, but placed in idealized position (O—H = 0.82 Å), and refined as riding, with Uiso(H) = 1.5 Ueq(O).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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
[Figure 1] Fig. 1. Molecular structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids. C-bound H atoms were omitted for clarity. For the disordered tert-butyl group, only major part is shown. Dashed line denotes hydrogen bond.
3,3',5,5'-Tetra-tert-butyl-2'-hydroxy-[1,1'-biphenyl]-2-yl 4-methylbenzenesulfonate top
Crystal data top
C35H48O4SZ = 2
Mr = 564.79F(000) = 612
Triclinic, P1Dx = 1.131 Mg m3
a = 9.885 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.948 (3) ÅCell parameters from 1685 reflections
c = 13.600 (3) Åθ = 2.3–23.6°
α = 101.761 (2)°µ = 0.13 mm1
β = 102.539 (2)°T = 296 K
γ = 92.004 (2)°Block, colourless
V = 1657.8 (6) Å30.28 × 0.22 × 0.21 mm
Data collection top
Bruker SMART APEXII
diffractometer
7609 independent reflections
Radiation source: fine-focus sealed tube3453 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
phi and ω scansθmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1212
Tmin = 0.965, Tmax = 0.973k = 1712
11516 measured reflectionsl = 1718
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.205H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0909P)2]
where P = (Fo2 + 2Fc2)/3
7609 reflections(Δ/σ)max = 0.001
389 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C35H48O4Sγ = 92.004 (2)°
Mr = 564.79V = 1657.8 (6) Å3
Triclinic, P1Z = 2
a = 9.885 (2) ÅMo Kα radiation
b = 12.948 (3) ŵ = 0.13 mm1
c = 13.600 (3) ÅT = 296 K
α = 101.761 (2)°0.28 × 0.22 × 0.21 mm
β = 102.539 (2)°
Data collection top
Bruker SMART APEXII
diffractometer
7609 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
3453 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 0.973Rint = 0.036
11516 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0740 restraints
wR(F2) = 0.205H-atom parameters constrained
S = 0.99Δρmax = 0.30 e Å3
7609 reflectionsΔρmin = 0.28 e Å3
389 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
xyzUiso*/UeqOcc. (<1)
S10.22545 (10)0.17764 (8)0.44203 (7)0.0562 (3)
O10.1844 (2)0.07858 (17)0.34604 (16)0.0449 (6)
O20.5120 (2)0.26901 (19)0.27643 (19)0.0600 (7)
H2A0.51030.25670.33300.090*
O30.1712 (3)0.1483 (3)0.5218 (2)0.0948 (11)
O40.3688 (3)0.2077 (2)0.45884 (19)0.0732 (8)
C10.3461 (3)0.0734 (2)0.2373 (2)0.0337 (7)
C20.2906 (3)0.0266 (2)0.3045 (2)0.0354 (7)
C30.3277 (3)0.0710 (2)0.3269 (2)0.0350 (7)
C40.4364 (3)0.1131 (2)0.2843 (2)0.0370 (7)
H4B0.46630.17680.29880.044*
C50.5024 (3)0.0665 (2)0.2222 (2)0.0364 (7)
C60.4537 (3)0.0270 (2)0.1985 (2)0.0373 (7)
H6A0.49420.05920.15560.045*
C70.2913 (3)0.1695 (2)0.2016 (2)0.0348 (7)
C80.3770 (3)0.2606 (3)0.2169 (2)0.0379 (8)
C90.3317 (3)0.3460 (3)0.1729 (2)0.0439 (8)
C100.1955 (3)0.3340 (3)0.1159 (2)0.0439 (8)
H10A0.16290.38950.08600.053*
C110.1041 (3)0.2450 (3)0.1002 (2)0.0425 (8)
C120.1548 (3)0.1631 (3)0.1449 (2)0.0396 (8)
H12A0.09650.10260.13680.047*
C130.1268 (4)0.2766 (3)0.4004 (2)0.0454 (9)
C140.1954 (4)0.3687 (3)0.3934 (3)0.0603 (10)
H14A0.29150.37460.40200.072*
C150.1179 (4)0.4518 (3)0.3734 (3)0.0672 (11)
H15A0.16410.51420.36960.081*
C160.0226 (4)0.4467 (3)0.3590 (3)0.0572 (10)
C170.0889 (4)0.3533 (3)0.3653 (3)0.0654 (11)
H17A0.18520.34740.35530.078*
C180.0154 (4)0.2684 (3)0.3861 (3)0.0596 (10)
H18A0.06180.20620.39030.072*
C190.6240 (3)0.1130 (3)0.1791 (2)0.0417 (8)
C200.6596 (4)0.2182 (3)0.2076 (4)0.0798 (13)
H20A0.58110.26940.17880.120*
H20B0.68260.20900.28130.120*
H20C0.73760.24270.18070.120*
C210.5913 (5)0.1263 (4)0.0628 (3)0.0905 (16)
H21A0.51010.17460.03260.136*
H21B0.66860.15390.03680.136*
H21C0.57450.05900.04540.136*
C220.7542 (4)0.0359 (3)0.2265 (3)0.0781 (13)
H22A0.77600.02750.30020.117*
H22B0.73720.03150.20930.117*
H22C0.83100.06350.19980.117*
C230.2605 (3)0.1305 (3)0.3933 (2)0.0405 (8)
C240.1016 (3)0.1278 (3)0.3695 (3)0.0634 (11)
H24A0.06360.15920.29790.095*
H24B0.07840.05580.38400.095*
H24C0.06350.16680.41150.095*
C250.3219 (4)0.0820 (3)0.5080 (2)0.0553 (10)
H25A0.27960.11900.54950.083*
H25B0.30410.00870.52270.083*
H25C0.42040.08790.52350.083*
C260.2909 (4)0.2467 (3)0.3749 (3)0.0616 (10)
H26A0.25260.28000.30390.092*
H26B0.24960.28150.41840.092*
H26C0.38960.25150.39070.092*
C270.4274 (4)0.4459 (3)0.1849 (3)0.0552 (10)
C280.3500 (5)0.5268 (3)0.1297 (4)0.0913 (15)
H28A0.27290.54750.15940.137*
H28B0.31650.49530.05770.137*
H28C0.41240.58790.13750.137*
C290.4797 (4)0.5009 (3)0.2986 (3)0.0705 (12)
H29A0.52890.45280.33570.106*
H29B0.40200.52240.32740.106*
H29C0.54100.56200.30410.106*
C300.5501 (4)0.4157 (3)0.1359 (3)0.0760 (12)
H30A0.60030.36540.16920.114*
H30B0.61090.47790.14400.114*
H30C0.51610.38500.06380.114*
C310.0447 (3)0.2368 (3)0.0343 (3)0.0540 (10)
C320.1409 (7)0.1544 (10)0.0610 (11)0.117 (6)0.682 (17)
H32A0.13830.08610.01810.175*0.682 (17)
H32B0.23440.17500.04910.175*0.682 (17)
H32C0.10940.15140.13220.175*0.682 (17)
C330.1088 (11)0.3421 (8)0.0594 (10)0.096 (4)0.682 (17)
H33A0.05110.39790.04850.143*0.682 (17)
H33B0.11580.35650.13010.143*0.682 (17)
H33C0.19990.33800.01530.143*0.682 (17)
C340.0426 (8)0.2085 (15)0.0744 (5)0.133 (8)0.682 (17)
H34A0.01500.26100.09050.200*0.682 (17)
H34B0.13550.20510.11550.200*0.682 (17)
H34C0.00600.14080.08900.200*0.682 (17)
C32'0.083 (2)0.1294 (14)0.036 (2)0.104 (10)0.318 (17)
H32D0.04010.12450.09310.156*0.318 (17)
H32E0.18220.11880.06010.156*0.318 (17)
H32F0.05120.07620.00190.156*0.318 (17)
C33'0.048 (3)0.315 (2)0.045 (3)0.19 (2)0.318 (17)
H33D0.04330.34970.03380.285*0.318 (17)
H33E0.11270.36680.03300.285*0.318 (17)
H33F0.07560.27440.11440.285*0.318 (17)
C34'0.139 (2)0.270 (4)0.096 (3)0.24 (3)0.318 (17)
H34D0.11810.34370.12720.354*0.318 (17)
H34E0.13230.22960.14820.354*0.318 (17)
H34F0.23210.25890.05320.354*0.318 (17)
C350.1038 (5)0.5394 (3)0.3377 (3)0.0850 (14)
H35A0.04090.59730.33690.128*
H35B0.15380.56080.39060.128*
H35C0.16840.51900.27190.128*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0638 (7)0.0656 (7)0.0409 (5)0.0307 (5)0.0173 (4)0.0055 (4)
O10.0382 (13)0.0497 (14)0.0511 (13)0.0144 (11)0.0198 (10)0.0089 (11)
O20.0435 (15)0.0594 (16)0.0722 (17)0.0024 (12)0.0002 (12)0.0173 (13)
O30.145 (3)0.111 (2)0.0595 (16)0.073 (2)0.0616 (18)0.0397 (17)
O40.0506 (17)0.077 (2)0.0697 (17)0.0227 (14)0.0067 (13)0.0153 (15)
C10.0331 (17)0.0364 (18)0.0316 (16)0.0068 (14)0.0079 (13)0.0064 (14)
C20.0300 (17)0.0417 (19)0.0336 (16)0.0078 (14)0.0080 (13)0.0047 (14)
C30.0322 (17)0.0376 (18)0.0339 (16)0.0025 (14)0.0072 (13)0.0049 (14)
C40.0379 (18)0.0336 (18)0.0397 (17)0.0075 (14)0.0083 (14)0.0081 (14)
C50.0386 (18)0.0387 (19)0.0331 (16)0.0076 (15)0.0109 (14)0.0070 (14)
C60.0385 (18)0.0404 (19)0.0359 (16)0.0077 (15)0.0139 (14)0.0087 (14)
C70.0343 (18)0.0357 (19)0.0363 (17)0.0089 (15)0.0103 (14)0.0088 (14)
C80.0279 (17)0.041 (2)0.0448 (18)0.0060 (15)0.0077 (14)0.0089 (15)
C90.045 (2)0.037 (2)0.052 (2)0.0086 (16)0.0145 (16)0.0104 (16)
C100.047 (2)0.039 (2)0.050 (2)0.0138 (17)0.0115 (16)0.0169 (16)
C110.042 (2)0.041 (2)0.0411 (18)0.0096 (17)0.0042 (15)0.0045 (16)
C120.0364 (19)0.0402 (19)0.0414 (18)0.0058 (15)0.0102 (14)0.0055 (15)
C130.047 (2)0.049 (2)0.0428 (19)0.0156 (18)0.0196 (16)0.0045 (16)
C140.048 (2)0.063 (3)0.072 (3)0.011 (2)0.025 (2)0.007 (2)
C150.069 (3)0.050 (2)0.084 (3)0.011 (2)0.027 (2)0.006 (2)
C160.064 (3)0.049 (2)0.055 (2)0.016 (2)0.0137 (19)0.0002 (19)
C170.041 (2)0.075 (3)0.077 (3)0.017 (2)0.0106 (19)0.011 (2)
C180.048 (2)0.061 (3)0.071 (3)0.012 (2)0.0174 (19)0.013 (2)
C190.043 (2)0.042 (2)0.0455 (19)0.0149 (17)0.0205 (16)0.0098 (16)
C200.084 (3)0.067 (3)0.114 (3)0.040 (2)0.061 (3)0.031 (3)
C210.095 (3)0.135 (4)0.047 (2)0.063 (3)0.030 (2)0.008 (2)
C220.051 (3)0.081 (3)0.105 (3)0.009 (2)0.035 (2)0.007 (3)
C230.0372 (19)0.044 (2)0.0434 (18)0.0045 (16)0.0141 (15)0.0111 (16)
C240.043 (2)0.079 (3)0.075 (3)0.004 (2)0.0185 (19)0.027 (2)
C250.064 (2)0.061 (2)0.047 (2)0.005 (2)0.0170 (18)0.0210 (18)
C260.077 (3)0.047 (2)0.069 (2)0.003 (2)0.029 (2)0.017 (2)
C270.055 (2)0.038 (2)0.077 (3)0.0006 (18)0.018 (2)0.020 (2)
C280.089 (3)0.053 (3)0.141 (4)0.001 (2)0.019 (3)0.051 (3)
C290.065 (3)0.047 (2)0.093 (3)0.007 (2)0.020 (2)0.000 (2)
C300.064 (3)0.077 (3)0.094 (3)0.008 (2)0.034 (2)0.022 (3)
C310.040 (2)0.062 (3)0.054 (2)0.0140 (19)0.0012 (17)0.0087 (19)
C320.034 (4)0.153 (10)0.159 (13)0.020 (5)0.024 (6)0.080 (9)
C330.055 (6)0.093 (7)0.130 (10)0.036 (5)0.000 (5)0.023 (6)
C340.053 (5)0.27 (2)0.045 (4)0.025 (9)0.004 (4)0.015 (8)
C32'0.069 (13)0.081 (13)0.12 (2)0.010 (10)0.046 (14)0.005 (12)
C33'0.17 (3)0.14 (2)0.20 (4)0.08 (2)0.14 (3)0.12 (3)
C34'0.040 (13)0.43 (8)0.14 (3)0.06 (3)0.008 (14)0.13 (4)
C350.090 (3)0.071 (3)0.087 (3)0.034 (3)0.010 (3)0.006 (3)
Geometric parameters (Å, º) top
S1—O41.413 (3)C23—C261.524 (4)
S1—O31.419 (3)C23—C251.536 (4)
S1—O11.602 (2)C23—C241.537 (4)
S1—C131.748 (3)C24—H24A0.9600
O1—C21.424 (3)C24—H24B0.9600
O2—C81.390 (3)C24—H24C0.9600
O2—H2A0.8200C25—H25A0.9600
C1—C21.387 (4)C25—H25B0.9600
C1—C61.390 (4)C25—H25C0.9600
C1—C71.502 (4)C26—H26A0.9600
C2—C31.402 (4)C26—H26B0.9600
C3—C41.403 (4)C26—H26C0.9600
C3—C231.537 (4)C27—C301.531 (5)
C4—C51.387 (4)C27—C291.532 (5)
C4—H4B0.9300C27—C281.540 (5)
C5—C61.391 (4)C28—H28A0.9600
C5—C191.537 (4)C28—H28B0.9600
C6—H6A0.9300C28—H28C0.9600
C7—C81.381 (4)C29—H29A0.9600
C7—C121.392 (4)C29—H29B0.9600
C8—C91.404 (4)C29—H29C0.9600
C9—C101.385 (4)C30—H30A0.9600
C9—C271.535 (5)C30—H30B0.9600
C10—C111.390 (5)C30—H30C0.9600
C10—H10A0.9300C31—C34'1.40 (2)
C11—C121.383 (4)C31—C341.454 (8)
C11—C311.535 (4)C31—C32'1.499 (16)
C12—H12A0.9300C31—C331.531 (10)
C13—C181.374 (5)C31—C321.552 (8)
C13—C141.382 (5)C31—C33'1.61 (2)
C14—C151.380 (5)C32—H32A0.9600
C14—H14A0.9300C32—H32B0.9600
C15—C161.358 (5)C32—H32C0.9600
C15—H15A0.9300C33—H33A0.9600
C16—C171.382 (5)C33—H33B0.9600
C16—C351.509 (5)C33—H33C0.9600
C17—C181.382 (5)C34—H34A0.9600
C17—H17A0.9300C34—H34B0.9600
C18—H18A0.9300C34—H34C0.9600
C19—C211.516 (5)C32'—H32D0.9600
C19—C201.523 (5)C32'—H32E0.9600
C19—C221.535 (5)C32'—H32F0.9600
C20—H20A0.9600C33'—H33D0.9600
C20—H20B0.9600C33'—H33E0.9600
C20—H20C0.9600C33'—H33F0.9600
C21—H21A0.9600C34'—H34D0.9600
C21—H21B0.9600C34'—H34E0.9600
C21—H21C0.9600C34'—H34F0.9600
C22—H22A0.9600C35—H35A0.9600
C22—H22B0.9600C35—H35B0.9600
C22—H22C0.9600C35—H35C0.9600
O4—S1—O3120.22 (19)C23—C25—H25B109.5
O4—S1—O1108.52 (13)H25A—C25—H25B109.5
O3—S1—O1105.68 (17)C23—C25—H25C109.5
O4—S1—C13110.24 (18)H25A—C25—H25C109.5
O3—S1—C13107.12 (16)H25B—C25—H25C109.5
O1—S1—C13103.78 (14)C23—C26—H26A109.5
C2—O1—S1119.80 (19)C23—C26—H26B109.5
C8—O2—H2A109.5H26A—C26—H26B109.5
C2—C1—C6118.4 (3)C23—C26—H26C109.5
C2—C1—C7122.9 (2)H26A—C26—H26C109.5
C6—C1—C7118.7 (3)H26B—C26—H26C109.5
C1—C2—C3123.2 (3)C30—C27—C29110.4 (3)
C1—C2—O1117.0 (3)C30—C27—C9109.2 (3)
C3—C2—O1119.7 (3)C29—C27—C9111.1 (3)
C2—C3—C4114.7 (3)C30—C27—C28107.8 (3)
C2—C3—C23125.1 (2)C29—C27—C28107.1 (3)
C4—C3—C23120.2 (3)C9—C27—C28111.1 (3)
C5—C4—C3124.7 (3)C27—C28—H28A109.5
C5—C4—H4B117.6C27—C28—H28B109.5
C3—C4—H4B117.6H28A—C28—H28B109.5
C4—C5—C6117.0 (3)C27—C28—H28C109.5
C4—C5—C19123.6 (3)H28A—C28—H28C109.5
C6—C5—C19119.5 (3)H28B—C28—H28C109.5
C1—C6—C5121.7 (3)C27—C29—H29A109.5
C1—C6—H6A119.2C27—C29—H29B109.5
C5—C6—H6A119.2H29A—C29—H29B109.5
C8—C7—C12119.6 (3)C27—C29—H29C109.5
C8—C7—C1121.1 (3)H29A—C29—H29C109.5
C12—C7—C1119.1 (3)H29B—C29—H29C109.5
C7—C8—O2120.0 (3)C27—C30—H30A109.5
C7—C8—C9121.6 (3)C27—C30—H30B109.5
O2—C8—C9118.4 (3)H30A—C30—H30B109.5
C10—C9—C8115.9 (3)C27—C30—H30C109.5
C10—C9—C27121.8 (3)H30A—C30—H30C109.5
C8—C9—C27122.3 (3)H30B—C30—H30C109.5
C9—C10—C11124.8 (3)C34'—C31—C34138.6 (13)
C9—C10—H10A117.6C34'—C31—C32'115 (2)
C11—C10—H10A117.6C34—C31—C32'53.6 (9)
C12—C11—C10116.7 (3)C34'—C31—C3348 (2)
C12—C11—C31121.5 (3)C34—C31—C33110.9 (7)
C10—C11—C31121.7 (3)C32'—C31—C33139.1 (8)
C11—C12—C7121.3 (3)C34'—C31—C11111.3 (11)
C11—C12—H12A119.3C34—C31—C11109.6 (4)
C7—C12—H12A119.3C32'—C31—C11111.2 (7)
C18—C13—C14120.2 (3)C33—C31—C11109.7 (5)
C18—C13—S1120.8 (3)C34'—C31—C3259 (2)
C14—C13—S1118.6 (3)C34—C31—C32110.2 (7)
C15—C14—C13118.4 (4)C32'—C31—C3259.9 (11)
C15—C14—H14A120.8C33—C31—C32104.9 (6)
C13—C14—H14A120.8C11—C31—C32111.5 (4)
C16—C15—C14123.0 (4)C34'—C31—C33'108 (2)
C16—C15—H15A118.5C34—C31—C33'52.3 (12)
C14—C15—H15A118.5C32'—C31—C33'103.5 (13)
C15—C16—C17117.4 (4)C33—C31—C33'62.6 (15)
C15—C16—C35121.5 (4)C11—C31—C33'108.0 (9)
C17—C16—C35121.1 (4)C32—C31—C33'140.5 (9)
C16—C17—C18121.6 (4)C31—C32—H32A109.5
C16—C17—H17A119.2C31—C32—H32B109.5
C18—C17—H17A119.2H32A—C32—H32B109.5
C13—C18—C17119.4 (4)C31—C32—H32C109.5
C13—C18—H18A120.3H32A—C32—H32C109.5
C17—C18—H18A120.3H32B—C32—H32C109.5
C21—C19—C20109.8 (3)C31—C33—H33A109.5
C21—C19—C22109.0 (3)C31—C33—H33B109.5
C20—C19—C22106.5 (3)H33A—C33—H33B109.5
C21—C19—C5110.1 (3)C31—C33—H33C109.5
C20—C19—C5112.8 (3)H33A—C33—H33C109.5
C22—C19—C5108.5 (3)H33B—C33—H33C109.5
C19—C20—H20A109.5C31—C34—H34A109.5
C19—C20—H20B109.5C31—C34—H34B109.5
H20A—C20—H20B109.5H34A—C34—H34B109.5
C19—C20—H20C109.5C31—C34—H34C109.5
H20A—C20—H20C109.5H34A—C34—H34C109.5
H20B—C20—H20C109.5H34B—C34—H34C109.5
C19—C21—H21A109.5C31—C32'—H32D109.5
C19—C21—H21B109.5C31—C32'—H32E109.5
H21A—C21—H21B109.5H32D—C32'—H32E109.5
C19—C21—H21C109.5C31—C32'—H32F109.5
H21A—C21—H21C109.5H32D—C32'—H32F109.5
H21B—C21—H21C109.5H32E—C32'—H32F109.5
C19—C22—H22A109.5C31—C33'—H33D109.5
C19—C22—H22B109.5C31—C33'—H33E109.5
H22A—C22—H22B109.5H33D—C33'—H33E109.5
C19—C22—H22C109.5C31—C33'—H33F109.5
H22A—C22—H22C109.5H33D—C33'—H33F109.5
H22B—C22—H22C109.5H33E—C33'—H33F109.5
C26—C23—C25107.1 (3)C31—C34'—H34D109.5
C26—C23—C3111.2 (2)C31—C34'—H34E109.5
C25—C23—C3109.5 (3)H34D—C34'—H34E109.5
C26—C23—C24107.1 (3)C31—C34'—H34F109.5
C25—C23—C24109.8 (3)H34D—C34'—H34F109.5
C3—C23—C24112.0 (3)H34E—C34'—H34F109.5
C23—C24—H24A109.5C16—C35—H35A109.5
C23—C24—H24B109.5C16—C35—H35B109.5
H24A—C24—H24B109.5H35A—C35—H35B109.5
C23—C24—H24C109.5C16—C35—H35C109.5
H24A—C24—H24C109.5H35A—C35—H35C109.5
H24B—C24—H24C109.5H35B—C35—H35C109.5
C23—C25—H25A109.5
O4—S1—O1—C29.7 (3)O4—S1—C13—C142.6 (3)
O3—S1—O1—C2120.5 (2)O3—S1—C13—C14129.8 (3)
C13—S1—O1—C2127.0 (2)O1—S1—C13—C14118.7 (3)
C6—C1—C2—C36.7 (4)C18—C13—C14—C151.0 (5)
C7—C1—C2—C3170.8 (3)S1—C13—C14—C15171.8 (3)
C6—C1—C2—O1177.5 (3)C13—C14—C15—C160.9 (6)
C7—C1—C2—O14.9 (4)C14—C15—C16—C170.2 (6)
S1—O1—C2—C180.7 (3)C14—C15—C16—C35179.8 (4)
S1—O1—C2—C3103.4 (3)C15—C16—C17—C180.4 (6)
C1—C2—C3—C46.2 (4)C35—C16—C17—C18179.2 (3)
O1—C2—C3—C4178.2 (3)C14—C13—C18—C170.4 (5)
C1—C2—C3—C23174.5 (3)S1—C13—C18—C17172.2 (3)
O1—C2—C3—C231.1 (4)C16—C17—C18—C130.3 (6)
C2—C3—C4—C51.8 (4)C4—C5—C19—C21125.8 (4)
C23—C3—C4—C5179.0 (3)C6—C5—C19—C2154.0 (4)
C3—C4—C5—C62.0 (5)C4—C5—C19—C202.8 (5)
C3—C4—C5—C19178.2 (3)C6—C5—C19—C20177.0 (3)
C2—C1—C6—C52.5 (4)C4—C5—C19—C22115.0 (4)
C7—C1—C6—C5175.1 (3)C6—C5—C19—C2265.2 (4)
C4—C5—C6—C11.6 (4)C2—C3—C23—C26162.0 (3)
C19—C5—C6—C1178.6 (3)C4—C3—C23—C2618.8 (4)
C2—C1—C7—C8123.0 (3)C2—C3—C23—C2579.9 (4)
C6—C1—C7—C859.5 (4)C4—C3—C23—C2599.3 (3)
C2—C1—C7—C1262.3 (4)C2—C3—C23—C2442.2 (4)
C6—C1—C7—C12115.2 (3)C4—C3—C23—C24138.6 (3)
C12—C7—C8—O2177.8 (3)C10—C9—C27—C30117.0 (4)
C1—C7—C8—O27.5 (4)C8—C9—C27—C3061.7 (4)
C12—C7—C8—C92.7 (4)C10—C9—C27—C29121.0 (3)
C1—C7—C8—C9172.0 (3)C8—C9—C27—C2960.3 (4)
C7—C8—C9—C101.6 (4)C10—C9—C27—C281.8 (5)
O2—C8—C9—C10178.9 (3)C8—C9—C27—C28179.4 (3)
C7—C8—C9—C27177.2 (3)C12—C11—C31—C34'87 (3)
O2—C8—C9—C272.3 (4)C10—C11—C31—C34'94 (3)
C8—C9—C10—C110.1 (5)C12—C11—C31—C3499.1 (9)
C27—C9—C10—C11178.7 (3)C10—C11—C31—C3479.3 (9)
C9—C10—C11—C120.3 (5)C12—C11—C31—C32'41.7 (14)
C9—C10—C11—C31178.8 (3)C10—C11—C31—C32'136.8 (14)
C10—C11—C12—C70.8 (4)C12—C11—C31—C33138.9 (6)
C31—C11—C12—C7177.8 (3)C10—C11—C31—C3342.7 (7)
C8—C7—C12—C112.3 (4)C12—C11—C31—C3223.1 (8)
C1—C7—C12—C11172.6 (3)C10—C11—C31—C32158.4 (7)
O4—S1—C13—C18175.4 (3)C12—C11—C31—C33'154.5 (18)
O3—S1—C13—C1842.9 (3)C10—C11—C31—C33'23.9 (18)
O1—S1—C13—C1868.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O40.822.593.322 (4)149
C24—H24C···O3i0.962.673.372 (4)130
C25—H25C···O4ii0.962.643.500 (4)150
C20—H20B···O3ii0.962.693.609 (5)160
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC35H48O4S
Mr564.79
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)9.885 (2), 12.948 (3), 13.600 (3)
α, β, γ (°)101.761 (2), 102.539 (2), 92.004 (2)
V3)1657.8 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.28 × 0.22 × 0.21
Data collection
DiffractometerBruker SMART APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.965, 0.973
No. of measured, independent and
observed [I > 2σ(I)] reflections
11516, 7609, 3453
Rint0.036
(sin θ/λ)max1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.205, 0.99
No. of reflections7609
No. of parameters389
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.28

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O40.822.593.322 (4)149.4
C24—H24C···O3i0.962.673.372 (4)130.4
C25—H25C···O4ii0.962.643.500 (4)149.5
C20—H20B···O3ii0.962.693.609 (5)159.5
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1.
 

Acknowledgements

We thank the National Natural Science Foundation of China (grant Nos. 21071069, 21171078 and 21271092) for financial support.

References

First citationBruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWang, C. & Wu, J. (2012). Acta Cryst. E68, o93.  Web of Science CSD CrossRef IUCr Journals
First citationWu, J., Pan, X., Wang, L. & Yao, L. (2009). Acta Cryst. E65, o155.  Web of Science CSD CrossRef IUCr Journals
First citationWu, J., Yu, T.-L., Chen, C.-T. & Lin, C.-C. (2006). Coord. Chem. Rev. 250, 602–626.  Web of Science CrossRef CAS

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