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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Pseudoaglycone of Spinosyn A

aSchool of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China
*Correspondence e-mail: , jrli@bit.edu.cn

(Received 21 May 2012; accepted 25 June 2012; online 18 July 2012)

The title compound [systematic name: 9-ethyl-13-hy­droxy-14-methyl-2-(3,4,5-trimeth­oxy-6-methyl­tetra­hydro-2H-pyran-2-yl­oxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodeca­hydro-1H-as-indaceno[3,2-d][1]oxacyclo­dodecine-7,15(2H,5aH)-dione], C33H50O9, was obtained by hydrolysis of Spinosyn A. The fused cyclo­pentene ring adopts a twisted conformation, while the fused cyclo­hexene and cyclo­pentane rings are in envelope conformations with the same C atom at the flaps. In the crystal, mol­ecules are linked by O—H⋯O and C—H⋯O hydrogen bonds into a layer parallel to the ab plane.

Related literature

For the insecticidal activity and research background of Spinosyn, see: Sparks et al. (2008[Sparks, T. C., Crouse, G. D., Dripps, J. E., Anzeveno, P., Martynow, J., DeAmicis, C. V. & Gifford, J. (2008). J. Comput. Aided Mol. Des. 22, 393-401.]); Thompson et al. (2000[Thompson, G. D., Dutton, R. & Sparks, T. C. (2000). Pest Manage. Sci. 56, 696-702.]); Salgado et al. (1998[Salgado, V. L. (1998). Pestic. Biochem. Physiol. 60, 91-102.]). For the structure of Spinosyn A, see: Evans & Black (1993[Evans, D. A. & Black, W. C. (1993). J. Am. Chem. Soc. 115, 4497-4513.]).

[Scheme 1]

Experimental

Crystal data
  • C33H50O9

  • Mr = 590.73

  • Orthorhombic, P 21 21 21

  • a = 8.7776 (15) Å

  • b = 8.7959 (15) Å

  • c = 41.737 (7) Å

  • V = 3222.4 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 153 K

  • 0.34 × 0.27 × 0.08 mm

Data collection
  • Rigaku AFC10/Saturn724+ diffractometer

  • 25322 measured reflections

  • 4876 independent reflections

  • 4194 reflections with I > 2σ(I)

  • Rint = 0.047

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.134

  • S = 1.00

  • 4876 reflections

  • 389 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.75 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O16—H16O⋯O18i 0.92 (4) 1.96 (3) 2.840 (3) 160 (3)
C3—H3B⋯O10ii 0.99 2.47 3.310 (3) 142
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]; (ii) x, y+1, z.

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2009[Rigaku/MSC (2009). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); software used to prepare material for publication: CrystalStructure.

Supporting information


Comment top

Spinosyns, a novel class of green pesticides, were characterized with high efficiency, fast degradation (Sparks et al., 2008), low toxicity (Thompson et al., 2000) and safety to environment (Salgado et al., 1998). Inspired by the high and broad insecticidal activity of Spinosyns and continuing our interest in its structure modification, we obtained pseudoaglycone of Spinosyn A from hydrolysis of the amino sugar forosamine. Here, we report the crystal structure of the title compound (Fig. 1).

Related literature top

For the insecticidal activity and research background of Spinosyn, see: Sparks et al. (2008); Thompson et al. (2000); Salgado et al. (1998). For the structure of Spinosyn A, see: Evans & Black (1993).

Experimental top

A solution of 2.0 g Spinosyn A (purchased from SHANGHAI HOHANCE GROUP, 98%) and 5eq H2SO4 was heated to 80 °C in ethanol (20 ml) for 2 h. The reaction mixture was cooled to room temperature and then filtered to give the title compound. The product was recrystallizated from ethanol to give colourless crystalline powder (m.p. 441–443 K).

Refinement top

C-bound H atoms were included in a riding model approximation with C—H distances 0.95–1.00 Å, and with Uiso(H) = 1.2Ueq(C). The H atom of OH group was located in a difference Fourrier map and refined freely [O—H = 0.92 (4) Å]. The absolute configuration was determined according to the structure of Spinosyn A (Evans & Black, 1993).

Structure description top

Spinosyns, a novel class of green pesticides, were characterized with high efficiency, fast degradation (Sparks et al., 2008), low toxicity (Thompson et al., 2000) and safety to environment (Salgado et al., 1998). Inspired by the high and broad insecticidal activity of Spinosyns and continuing our interest in its structure modification, we obtained pseudoaglycone of Spinosyn A from hydrolysis of the amino sugar forosamine. Here, we report the crystal structure of the title compound (Fig. 1).

For the insecticidal activity and research background of Spinosyn, see: Sparks et al. (2008); Thompson et al. (2000); Salgado et al. (1998). For the structure of Spinosyn A, see: Evans & Black (1993).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku/MSC, 2009); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
9-ethyl-13-hydroxy-14-methyl-2-(3,4,5-trimethoxy-6-methyltetrahydro-2H- pyran-2-yloxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H- as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)- dione top
Crystal data top
C33H50O9F(000) = 1280
Mr = 590.73Dx = 1.218 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 11776 reflections
a = 8.7776 (15) Åθ = 2.4–29.1°
b = 8.7959 (15) ŵ = 0.09 mm1
c = 41.737 (7) ÅT = 153 K
V = 3222.4 (10) Å3Platelet, colorless
Z = 40.34 × 0.27 × 0.08 mm
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
4194 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.047
Graphite monochromatorθmax = 29.1°, θmin = 2.4°
Detector resolution: 28.5714 pixels mm-1h = 1012
φ and ω scansk = 1112
25322 measured reflectionsl = 5743
4876 independent reflections
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0696P)2 + 0.586P]
where P = (Fo2 + 2Fc2)/3
4876 reflections(Δ/σ)max = 0.001
389 parametersΔρmax = 0.75 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C33H50O9V = 3222.4 (10) Å3
Mr = 590.73Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.7776 (15) ŵ = 0.09 mm1
b = 8.7959 (15) ÅT = 153 K
c = 41.737 (7) Å0.34 × 0.27 × 0.08 mm
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
4194 reflections with I > 2σ(I)
25322 measured reflectionsRint = 0.047
4876 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.134H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.75 e Å3
4876 reflectionsΔρmin = 0.22 e Å3
389 parameters
Special details top

Experimental. Spectral data: IR (KBr): 3517, 2968, 2930, 1624, 1650, 1606, 1457, 1379, cm-1; MS (MALDI-TOF) m/z: [M+Na]+ 613.3.

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*/Ueq
O100.5636 (3)0.0686 (2)0.89590 (4)0.0513 (6)
O110.5456 (2)0.04001 (18)0.94906 (4)0.0318 (4)
O160.0506 (2)0.1699 (2)0.96650 (5)0.0425 (5)
O180.3702 (2)0.4082 (2)0.96960 (4)0.0375 (4)
O230.2851 (2)0.94913 (19)0.81098 (4)0.0368 (4)
O250.2547 (2)1.3408 (2)0.78898 (4)0.0412 (5)
O260.0084 (3)1.2315 (2)0.75097 (5)0.0403 (4)
O270.1883 (2)1.1350 (2)0.80154 (5)0.0455 (5)
O290.1799 (2)1.1452 (2)0.84138 (4)0.0357 (4)
C10.3003 (3)0.7119 (3)0.84098 (6)0.0350 (5)
H1A0.21020.71090.85530.042*
H1B0.27320.66490.82020.042*
C20.3627 (3)0.8721 (3)0.83662 (6)0.0340 (5)
H20.34650.93030.85690.041*
C30.5355 (3)0.8560 (3)0.83072 (7)0.0386 (6)
H3A0.56230.88820.80870.046*
H3B0.59400.91820.84620.046*
C40.5683 (3)0.6857 (3)0.83553 (6)0.0319 (5)
H40.55980.63410.81430.038*
C50.7166 (3)0.6402 (3)0.85043 (7)0.0386 (6)
H50.80540.69960.84680.046*
C60.7238 (3)0.5161 (3)0.86879 (6)0.0358 (5)
H60.81960.49100.87790.043*
C70.5914 (3)0.4131 (3)0.87605 (6)0.0313 (5)
H70.61750.30890.86810.038*
C80.5579 (3)0.4018 (3)0.91260 (6)0.0295 (5)
H80.58800.50040.92270.035*
C90.6420 (3)0.2733 (3)0.93019 (6)0.0307 (5)
H9A0.75130.27660.92430.037*
H9B0.63450.29070.95360.037*
C100.5798 (3)0.1174 (3)0.92253 (6)0.0315 (5)
C120.5017 (3)0.1199 (3)0.94565 (7)0.0357 (5)
H120.49910.14710.92240.043*
C130.3448 (4)0.1438 (3)0.95999 (9)0.0489 (7)
H13A0.35460.14660.98360.059*
H13B0.30630.24420.95300.059*
C140.2249 (4)0.0210 (3)0.95098 (8)0.0449 (7)
H14A0.25740.03280.93130.054*
H14B0.12540.07010.94670.054*
C150.2085 (3)0.0922 (3)0.97844 (7)0.0381 (6)
H15A0.17350.03610.99760.046*
H15B0.31070.13380.98340.046*
C160.1004 (3)0.2250 (3)0.97290 (6)0.0355 (5)
H160.09750.28880.99270.043*
C170.1391 (3)0.3263 (3)0.94464 (6)0.0313 (5)
H170.11690.26960.92440.038*
C180.3045 (3)0.3737 (3)0.94445 (6)0.0293 (5)
C190.3866 (3)0.3896 (3)0.91396 (6)0.0293 (5)
C200.3231 (3)0.4125 (3)0.88526 (6)0.0311 (5)
H200.21760.39980.88090.037*
C210.4377 (3)0.4603 (3)0.86074 (6)0.0297 (5)
H210.42070.40680.83990.036*
C220.4360 (3)0.6331 (3)0.85635 (6)0.0292 (5)
H220.45050.67940.87800.035*
C240.2789 (3)1.1066 (3)0.81606 (6)0.0336 (5)
H240.38351.14310.82160.040*
C250.2305 (3)1.1817 (3)0.78489 (6)0.0342 (5)
H250.29561.14350.76700.041*
C260.0631 (3)1.1468 (3)0.77771 (6)0.0334 (5)
H260.05291.03600.77290.040*
C270.0359 (3)1.1844 (3)0.80648 (6)0.0351 (5)
H270.03451.29650.81040.042*
C280.0250 (3)1.1013 (3)0.83596 (6)0.0367 (5)
H280.02090.98920.83200.044*
C1210.6240 (4)0.2127 (3)0.96221 (7)0.0422 (6)
H12A0.63350.17770.98470.051*
H12B0.59200.32060.96270.051*
C1220.7782 (4)0.2017 (4)0.94616 (9)0.0537 (8)
H12C0.81210.09550.94610.064*
H12D0.77030.23820.92400.064*
H12E0.85190.26410.95790.064*
C1710.0413 (3)0.4720 (3)0.94530 (8)0.0438 (6)
H17A0.05940.53080.92570.053*
H17B0.06900.53330.96400.053*
H17C0.06670.44440.94660.053*
C2510.3124 (4)1.4170 (4)0.76164 (8)0.0516 (8)
H25A0.23651.41390.74440.062*
H25B0.40611.36680.75450.062*
H25C0.33471.52300.76710.062*
C2610.0420 (4)1.1631 (4)0.72113 (7)0.0528 (8)
H26A0.00061.06010.72060.063*
H26B0.15271.15800.71830.063*
H26C0.00291.22370.70380.063*
C2710.2890 (4)1.2497 (4)0.79068 (8)0.0524 (8)
H27A0.25581.28590.76960.063*
H27B0.28861.33460.80590.063*
H27C0.39221.20800.78900.063*
C2810.0613 (4)1.1369 (4)0.86623 (7)0.0502 (7)
H28A0.05671.24640.87040.060*
H28B0.01541.08170.88420.060*
H28C0.16781.10560.86380.060*
H16O0.083 (4)0.123 (4)0.9849 (8)0.057 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O100.0789 (16)0.0422 (10)0.0329 (10)0.0082 (11)0.0023 (11)0.0019 (8)
O110.0363 (9)0.0259 (7)0.0333 (9)0.0026 (7)0.0007 (7)0.0025 (6)
O160.0279 (9)0.0581 (12)0.0415 (11)0.0038 (9)0.0016 (8)0.0115 (9)
O180.0358 (10)0.0461 (10)0.0307 (9)0.0012 (8)0.0039 (8)0.0016 (7)
O230.0478 (11)0.0299 (8)0.0327 (9)0.0108 (8)0.0055 (8)0.0000 (7)
O250.0510 (12)0.0312 (9)0.0415 (10)0.0039 (8)0.0036 (9)0.0063 (7)
O260.0445 (10)0.0424 (10)0.0339 (9)0.0078 (8)0.0048 (8)0.0037 (8)
O270.0357 (11)0.0481 (11)0.0527 (12)0.0028 (9)0.0035 (9)0.0016 (9)
O290.0401 (10)0.0347 (9)0.0324 (9)0.0062 (8)0.0021 (8)0.0028 (7)
C10.0333 (13)0.0378 (13)0.0340 (13)0.0042 (10)0.0005 (11)0.0060 (10)
C20.0408 (14)0.0318 (12)0.0295 (12)0.0066 (10)0.0033 (11)0.0012 (9)
C30.0407 (15)0.0314 (12)0.0438 (14)0.0002 (11)0.0017 (12)0.0052 (10)
C40.0322 (12)0.0308 (11)0.0328 (12)0.0011 (10)0.0000 (10)0.0028 (9)
C50.0310 (13)0.0403 (13)0.0445 (14)0.0004 (11)0.0022 (11)0.0069 (11)
C60.0256 (12)0.0418 (13)0.0399 (13)0.0040 (10)0.0017 (10)0.0072 (10)
C70.0297 (12)0.0309 (11)0.0332 (12)0.0047 (9)0.0002 (10)0.0033 (9)
C80.0288 (11)0.0290 (10)0.0307 (11)0.0001 (9)0.0013 (10)0.0007 (9)
C90.0269 (11)0.0314 (11)0.0339 (12)0.0021 (9)0.0040 (10)0.0027 (9)
C100.0292 (12)0.0329 (11)0.0324 (12)0.0035 (10)0.0013 (10)0.0007 (9)
C120.0391 (14)0.0241 (11)0.0439 (14)0.0040 (10)0.0016 (11)0.0024 (10)
C130.0447 (16)0.0284 (12)0.074 (2)0.0017 (12)0.0100 (15)0.0042 (13)
C140.0382 (15)0.0390 (14)0.0574 (18)0.0019 (12)0.0014 (13)0.0047 (12)
C150.0345 (13)0.0362 (12)0.0435 (14)0.0004 (11)0.0013 (12)0.0068 (10)
C160.0293 (12)0.0416 (13)0.0356 (13)0.0024 (10)0.0020 (10)0.0018 (10)
C170.0272 (12)0.0341 (12)0.0328 (12)0.0036 (9)0.0035 (10)0.0010 (10)
C180.0272 (11)0.0306 (11)0.0302 (11)0.0042 (9)0.0023 (9)0.0012 (9)
C190.0276 (11)0.0286 (11)0.0316 (11)0.0025 (9)0.0009 (9)0.0009 (9)
C200.0293 (12)0.0294 (11)0.0346 (12)0.0019 (9)0.0017 (10)0.0007 (9)
C210.0306 (12)0.0305 (10)0.0280 (11)0.0007 (10)0.0025 (9)0.0017 (9)
C220.0289 (11)0.0314 (11)0.0274 (11)0.0026 (9)0.0010 (9)0.0003 (8)
C240.0348 (13)0.0322 (12)0.0338 (12)0.0057 (10)0.0004 (10)0.0015 (9)
C250.0376 (14)0.0284 (11)0.0366 (13)0.0025 (10)0.0015 (11)0.0026 (9)
C260.0389 (13)0.0292 (11)0.0321 (12)0.0028 (10)0.0035 (11)0.0003 (9)
C270.0334 (13)0.0336 (12)0.0383 (13)0.0011 (10)0.0042 (11)0.0012 (10)
C280.0393 (14)0.0359 (12)0.0350 (13)0.0037 (11)0.0009 (11)0.0007 (10)
C1210.0507 (17)0.0298 (12)0.0460 (15)0.0121 (11)0.0019 (13)0.0022 (11)
C1220.0465 (18)0.0461 (16)0.069 (2)0.0170 (14)0.0014 (16)0.0023 (15)
C1710.0347 (14)0.0420 (14)0.0547 (16)0.0071 (12)0.0002 (13)0.0040 (13)
C2510.0525 (19)0.0458 (16)0.0565 (18)0.0060 (14)0.0004 (15)0.0164 (13)
C2610.060 (2)0.0646 (19)0.0341 (14)0.0067 (17)0.0037 (14)0.0034 (13)
C2710.0355 (15)0.069 (2)0.0528 (18)0.0098 (15)0.0034 (14)0.0046 (15)
C2810.0521 (18)0.0603 (18)0.0383 (15)0.0103 (16)0.0090 (14)0.0005 (13)
Geometric parameters (Å, º) top
O10—C101.200 (3)C14—H14A0.9900
O11—C101.334 (3)C14—H14B0.9900
O11—C121.465 (3)C15—C161.523 (4)
O16—C161.436 (3)C15—H15A0.9900
O16—H16O0.92 (4)C15—H15B0.9900
O18—C181.236 (3)C16—C171.517 (3)
O23—C241.402 (3)C16—H161.0000
O23—C21.438 (3)C17—C181.510 (3)
O25—C2511.417 (3)C17—C1711.543 (4)
O25—C251.425 (3)C17—H171.0000
O26—C2611.414 (3)C18—C191.469 (3)
O26—C261.425 (3)C19—C201.336 (3)
O27—C2711.416 (4)C20—C211.496 (3)
O27—C271.421 (3)C20—H200.9500
O29—C241.410 (3)C21—C221.531 (3)
O29—C281.432 (3)C21—H211.0000
C1—C221.520 (3)C22—H221.0000
C1—C21.523 (4)C24—C251.519 (3)
C1—H1A0.9900C24—H241.0000
C1—H1B0.9900C25—C261.531 (4)
C2—C31.543 (4)C25—H251.0000
C2—H21.0000C26—C271.518 (4)
C3—C41.538 (3)C26—H261.0000
C3—H3A0.9900C27—C281.527 (4)
C3—H3B0.9900C27—H271.0000
C4—C51.497 (4)C28—C2811.506 (4)
C4—C221.522 (3)C28—H281.0000
C4—H41.0000C121—C1221.513 (5)
C5—C61.335 (4)C121—H12A0.9900
C5—H50.9500C121—H12B0.9900
C6—C71.505 (4)C122—H12C0.9800
C6—H60.9500C122—H12D0.9800
C7—C211.550 (3)C122—H12E0.9800
C7—C81.557 (3)C171—H17A0.9800
C7—H71.0000C171—H17B0.9800
C8—C191.509 (3)C171—H17C0.9800
C8—C91.537 (3)C251—H25A0.9800
C8—H81.0000C251—H25B0.9800
C9—C101.511 (3)C251—H25C0.9800
C9—H9A0.9900C261—H26A0.9800
C9—H9B0.9900C261—H26B0.9800
C12—C1211.516 (4)C261—H26C0.9800
C12—C131.516 (4)C271—H27A0.9800
C12—H121.0000C271—H27B0.9800
C13—C141.554 (4)C271—H27C0.9800
C13—H13A0.9900C281—H28A0.9800
C13—H13B0.9900C281—H28B0.9800
C14—C151.525 (4)C281—H28C0.9800
C10—O11—C12117.9 (2)O18—C18—C19118.9 (2)
C16—O16—H16O106 (2)O18—C18—C17120.8 (2)
C24—O23—C2111.83 (19)C19—C18—C17120.1 (2)
C251—O25—C25114.9 (2)C20—C19—C18125.9 (2)
C261—O26—C26113.4 (2)C20—C19—C8111.8 (2)
C271—O27—C27114.6 (2)C18—C19—C8121.9 (2)
C24—O29—C28113.7 (2)C19—C20—C21112.0 (2)
C22—C1—C2101.0 (2)C19—C20—H20124.0
C22—C1—H1A111.6C21—C20—H20124.0
C2—C1—H1A111.6C20—C21—C22110.8 (2)
C22—C1—H1B111.6C20—C21—C7103.17 (18)
C2—C1—H1B111.6C22—C21—C7108.9 (2)
H1A—C1—H1B109.4C20—C21—H21111.2
O23—C2—C1110.8 (2)C22—C21—H21111.2
O23—C2—C3112.9 (2)C7—C21—H21111.2
C1—C2—C3106.7 (2)C1—C22—C4102.61 (19)
O23—C2—H2108.8C1—C22—C21120.7 (2)
C1—C2—H2108.8C4—C22—C21111.3 (2)
C3—C2—H2108.8C1—C22—H22107.2
C4—C3—C2104.6 (2)C4—C22—H22107.2
C4—C3—H3A110.8C21—C22—H22107.2
C2—C3—H3A110.8O23—C24—O29112.0 (2)
C4—C3—H3B110.8O23—C24—C25108.1 (2)
C2—C3—H3B110.8O29—C24—C25111.4 (2)
H3A—C3—H3B108.9O23—C24—H24108.4
C5—C4—C22110.2 (2)O29—C24—H24108.4
C5—C4—C3118.5 (2)C25—C24—H24108.4
C22—C4—C3103.2 (2)O25—C25—C24106.4 (2)
C5—C4—H4108.2O25—C25—C26111.3 (2)
C22—C4—H4108.2C24—C25—C26110.4 (2)
C3—C4—H4108.2O25—C25—H25109.5
C6—C5—C4119.9 (2)C24—C25—H25109.5
C6—C5—H5120.1C26—C25—H25109.5
C4—C5—H5120.1O26—C26—C27108.2 (2)
C5—C6—C7124.9 (2)O26—C26—C25111.8 (2)
C5—C6—H6117.6C27—C26—C25110.5 (2)
C7—C6—H6117.6O26—C26—H26108.7
C6—C7—C21115.32 (19)C27—C26—H26108.7
C6—C7—C8112.4 (2)C25—C26—H26108.7
C21—C7—C8104.87 (19)O27—C27—C26110.9 (2)
C6—C7—H7108.0O27—C27—C28107.5 (2)
C21—C7—H7108.0C26—C27—C28109.4 (2)
C8—C7—H7108.0O27—C27—H27109.7
C19—C8—C9114.1 (2)C26—C27—H27109.7
C19—C8—C7103.3 (2)C28—C27—H27109.7
C9—C8—C7115.1 (2)O29—C28—C281106.8 (2)
C19—C8—H8108.0O29—C28—C27109.3 (2)
C9—C8—H8108.0C281—C28—C27113.6 (2)
C7—C8—H8108.0O29—C28—H28109.0
C10—C9—C8113.1 (2)C281—C28—H28109.0
C10—C9—H9A109.0C27—C28—H28109.0
C8—C9—H9A109.0C122—C121—C12113.4 (2)
C10—C9—H9B109.0C122—C121—H12A108.9
C8—C9—H9B109.0C12—C121—H12A108.9
H9A—C9—H9B107.8C122—C121—H12B108.9
O10—C10—O11124.0 (2)C12—C121—H12B108.9
O10—C10—C9124.3 (2)H12A—C121—H12B107.7
O11—C10—C9111.6 (2)C121—C122—H12C109.5
O11—C12—C121106.6 (2)C121—C122—H12D109.5
O11—C12—C13109.5 (2)H12C—C122—H12D109.5
C121—C12—C13112.9 (2)C121—C122—H12E109.5
O11—C12—H12109.3H12C—C122—H12E109.5
C121—C12—H12109.3H12D—C122—H12E109.5
C13—C12—H12109.3C17—C171—H17A109.5
C12—C13—C14115.1 (2)C17—C171—H17B109.5
C12—C13—H13A108.5H17A—C171—H17B109.5
C14—C13—H13A108.5C17—C171—H17C109.5
C12—C13—H13B108.5H17A—C171—H17C109.5
C14—C13—H13B108.5H17B—C171—H17C109.5
H13A—C13—H13B107.5O25—C251—H25A109.5
C15—C14—C13109.6 (3)O25—C251—H25B109.5
C15—C14—H14A109.8H25A—C251—H25B109.5
C13—C14—H14A109.8O25—C251—H25C109.5
C15—C14—H14B109.8H25A—C251—H25C109.5
C13—C14—H14B109.8H25B—C251—H25C109.5
H14A—C14—H14B108.2O26—C261—H26A109.5
C16—C15—C14116.5 (2)O26—C261—H26B109.5
C16—C15—H15A108.2H26A—C261—H26B109.5
C14—C15—H15A108.2O26—C261—H26C109.5
C16—C15—H15B108.2H26A—C261—H26C109.5
C14—C15—H15B108.2H26B—C261—H26C109.5
H15A—C15—H15B107.3O27—C271—H27A109.5
O16—C16—C17105.1 (2)O27—C271—H27B109.5
O16—C16—C15110.1 (2)H27A—C271—H27B109.5
C17—C16—C15115.4 (2)O27—C271—H27C109.5
O16—C16—H16108.7H27A—C271—H27C109.5
C17—C16—H16108.7H27B—C271—H27C109.5
C15—C16—H16108.7C28—C281—H28A109.5
C18—C17—C16112.4 (2)C28—C281—H28B109.5
C18—C17—C171107.8 (2)H28A—C281—H28B109.5
C16—C17—C171110.4 (2)C28—C281—H28C109.5
C18—C17—H17108.7H28A—C281—H28C109.5
C16—C17—H17108.7H28B—C281—H28C109.5
C171—C17—H17108.7
C24—O23—C2—C1149.8 (2)C8—C19—C20—C216.2 (3)
C24—O23—C2—C390.6 (3)C19—C20—C21—C2298.5 (2)
C22—C1—C2—O23155.1 (2)C19—C20—C21—C717.9 (3)
C22—C1—C2—C331.7 (3)C6—C7—C21—C20146.0 (2)
O23—C2—C3—C4127.8 (2)C8—C7—C21—C2021.8 (2)
C1—C2—C3—C45.8 (3)C6—C7—C21—C2228.2 (3)
C2—C3—C4—C5144.5 (2)C8—C7—C21—C2296.0 (2)
C2—C3—C4—C2222.5 (3)C2—C1—C22—C446.0 (2)
C22—C4—C5—C629.0 (3)C2—C1—C22—C21170.4 (2)
C3—C4—C5—C6147.4 (3)C5—C4—C22—C1170.4 (2)
C4—C5—C6—C70.3 (4)C3—C4—C22—C143.0 (2)
C5—C6—C7—C210.5 (4)C5—C4—C22—C2159.1 (3)
C5—C6—C7—C8120.7 (3)C3—C4—C22—C21173.4 (2)
C6—C7—C8—C19144.5 (2)C20—C21—C22—C168.8 (3)
C21—C7—C8—C1918.5 (2)C7—C21—C22—C1178.4 (2)
C6—C7—C8—C990.5 (3)C20—C21—C22—C4171.0 (2)
C21—C7—C8—C9143.5 (2)C7—C21—C22—C458.2 (3)
C19—C8—C9—C1046.5 (3)C2—O23—C24—O2970.2 (3)
C7—C8—C9—C1072.7 (3)C2—O23—C24—C25166.7 (2)
C12—O11—C10—O107.1 (4)C28—O29—C24—O2361.6 (3)
C12—O11—C10—C9172.6 (2)C28—O29—C24—C2559.7 (3)
C8—C9—C10—O1053.0 (4)C251—O25—C25—C24141.0 (2)
C8—C9—C10—O11127.4 (2)C251—O25—C25—C2698.7 (3)
C10—O11—C12—C121115.1 (2)O23—C24—C25—O25168.6 (2)
C10—O11—C12—C13122.4 (3)O29—C24—C25—O2567.8 (3)
O11—C12—C13—C1444.8 (3)O23—C24—C25—C2670.4 (3)
C121—C12—C13—C14163.4 (3)O29—C24—C25—C2653.1 (3)
C12—C13—C14—C15100.1 (3)C261—O26—C26—C27154.1 (2)
C13—C14—C15—C16177.2 (2)C261—O26—C26—C2583.9 (3)
C14—C15—C16—O1659.5 (3)O25—C25—C26—O2654.3 (3)
C14—C15—C16—C1759.3 (3)C24—C25—C26—O26172.3 (2)
O16—C16—C17—C18170.3 (2)O25—C25—C26—C2766.4 (3)
C15—C16—C17—C1848.8 (3)C24—C25—C26—C2751.6 (3)
O16—C16—C17—C17169.2 (3)C271—O27—C27—C2697.4 (3)
C15—C16—C17—C171169.3 (2)C271—O27—C27—C28143.0 (2)
C16—C17—C18—O1840.1 (3)O26—C26—C27—O2764.4 (3)
C171—C17—C18—O1881.8 (3)C25—C26—C27—O27172.8 (2)
C16—C17—C18—C19144.2 (2)O26—C26—C27—C28177.2 (2)
C171—C17—C18—C1993.9 (3)C25—C26—C27—C2854.4 (3)
O18—C18—C19—C20153.7 (2)C24—O29—C28—C281174.7 (2)
C17—C18—C19—C2022.1 (4)C24—O29—C28—C2762.0 (3)
O18—C18—C19—C818.1 (4)O27—C27—C28—O29178.69 (19)
C17—C18—C19—C8166.1 (2)C26—C27—C28—O2958.1 (3)
C9—C8—C19—C20133.9 (2)O27—C27—C28—C28162.2 (3)
C7—C8—C19—C208.3 (3)C26—C27—C28—C281177.3 (2)
C9—C8—C19—C1853.3 (3)O11—C12—C121—C12265.3 (3)
C7—C8—C19—C18178.9 (2)C13—C12—C121—C122174.4 (3)
C18—C19—C20—C21166.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O16—H16O···O18i0.92 (4)1.96 (3)2.840 (3)160 (3)
C3—H3B···O10ii0.992.473.310 (3)142
Symmetry codes: (i) x1/2, y+1/2, z+2; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC33H50O9
Mr590.73
Crystal system, space groupOrthorhombic, P212121
Temperature (K)153
a, b, c (Å)8.7776 (15), 8.7959 (15), 41.737 (7)
V3)3222.4 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.34 × 0.27 × 0.08
Data collection
DiffractometerRigaku AFC10/Saturn724+
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
25322, 4876, 4194
Rint0.047
(sin θ/λ)max1)0.685
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.134, 1.00
No. of reflections4876
No. of parameters389
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.75, 0.22

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O16—H16O···O18i0.92 (4)1.96 (3)2.840 (3)160 (3)
C3—H3B···O10ii0.992.473.310 (3)142
Symmetry codes: (i) x1/2, y+1/2, z+2; (ii) x, y+1, z.
 

Acknowledgements

The authors thank Beijing Institute of Technology for the X-ray diffraction analysis.

References

First citationEvans, D. A. & Black, W. C. (1993). J. Am. Chem. Soc. 115, 4497–4513.  CrossRef CAS Web of Science Google Scholar
First citationRigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2009). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
First citationSalgado, V. L. (1998). Pestic. Biochem. Physiol. 60, 91–102.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSparks, T. C., Crouse, G. D., Dripps, J. E., Anzeveno, P., Martynow, J., DeAmicis, C. V. & Gifford, J. (2008). J. Comput. Aided Mol. Des. 22, 393–401.  Web of Science CrossRef PubMed CAS Google Scholar
First citationThompson, G. D., Dutton, R. & Sparks, T. C. (2000). Pest Manage. Sci. 56, 696–702.  Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds