PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o336.
Published online 2007 December 21. doi:  10.1107/S1600536807065695
PMCID: PMC2915377

(E)-2-(Cyclo­hexyl­methyl­ene)succinic acid

Abstract

The title compound, C11H16O4, crystallizes with three molecules in the asymmetric unit. The cyclo­hexane ring adopts a chair conformation. Inter­molecular O—H(...)O hydrogen bonds are observed and these help to establish the crystal packing.

Related literature

For related literature, see: Stobbe (1893 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o336-scheme1.jpg

Experimental

Crystal data

  • C11H16O4
  • M r = 212.24
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o336-efi1.jpg
  • a = 10.530 (2) Å
  • b = 18.762 (4) Å
  • c = 16.982 (3) Å
  • β = 91.42 (3)°
  • V = 3354.2 (12) Å3
  • Z = 12
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 113 (2) K
  • 0.10 × 0.08 × 0.06 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.981, T max = 0.994
  • 20420 measured reflections
  • 5924 independent reflections
  • 4780 reflections with I > 2σ(I)
  • R int = 0.063

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.136
  • S = 1.11
  • 5924 reflections
  • 424 parameters
  • 6 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Bruker, 1997 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807065695/gw2033sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065695/gw2033Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

The title compound is obtained by the condensation between dimethylsuccinate and cyclohexanecarbaldehyde. We report here the crystal structure of the title compound (Fig. 1).

In the title compound, C11H16O4, the cyclohexane ring adopts chair conformation. Intermolecular O—H···O hydrogen bonds are observed. They help to establish the crystal packing.

Experimental

The title compound was prepared according to the method of Stobbe condensation (Stobbe et al.,1893). To a room temperature stirred solution of 50% NaH (1.06 g, 0.022 mol) in anhydrous toluene (20 ml), a solution of dimethylsuccinate (3.2 g, 0.022 mol) and anhydrous methanol (1 ml) in anhydrous toluene (10 ml) was added dropwise. The mixture was stirred for 1 h, and then a solution of cyclohexanecarbaldehyde (2.24 g, 0.02 mol) in anhydrous toluene (20 ml) was added dropwise. The mixture was stirred at room temperature for 3 h and water (30 ml) was added. The water phase was washed with ethyl acetatethree times and then sodium hydroxide (3 g, 0.075 mol) was added. The mixture was refluxed for 4 and then acidified with hydrochloric acid to PH 2 and extracted with ethyl acetate. The organic layer was dried with anhydrous Mg2SO4, and then concentrated in vacuo. The title compound (3.65 g) was obtained in powder form in a yield of 86.1%. Crystals of (I) were obtained by slow evaporation of a solution of ethanol (m.p. 477–478 K).

Refinement

All H atoms were positioned geometrically (C—H=0.95–0.99 Å), and refined as riding with Uiso(H)=1.2Ueq(carrier) or 1.5eq(methyl groups).

Figures

Fig. 1.
A view of the molecular of (I). Displacement ellopsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

Crystal data

C11H16O4Dx = 1.261 Mg m3
Mr = 212.24Melting point = 477–478 K
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
a = 10.530 (2) ÅCell parameters from 266 reflections
b = 18.762 (4) Åθ = 1.6–27.9º
c = 16.982 (3) ŵ = 0.10 mm1
β = 91.42 (3)ºT = 113 (2) K
V = 3354.2 (12) Å3Block, colorless
Z = 120.10 × 0.08 × 0.06 mm
F000 = 1368

Data collection

Rigaku Saturn diffractometer5924 independent reflections
Radiation source: fine-focus sealed tube4780 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.063
T = 113(2) Kθmax = 25.0º
ω scansθmin = 1.6º
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)h = −12→12
Tmin = 0.981, Tmax = 0.994k = −22→17
20420 measured reflectionsl = −20→20

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.136  w = 1/[σ2(Fo2) + (0.0559P)2 + 0.7047P] where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.001
5924 reflectionsΔρmax = 0.21 e Å3
424 parametersΔρmin = −0.27 e Å3
6 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/Ueq
O10.52956 (15)0.70841 (9)0.41522 (9)0.0304 (4)
H10.484 (2)0.6721 (13)0.4393 (15)0.046*
O20.66462 (15)0.69150 (9)0.51719 (9)0.0332 (4)
O30.99241 (18)0.73367 (10)0.54599 (10)0.0411 (5)
H31.041 (3)0.6941 (14)0.5465 (18)0.062*
O40.92339 (15)0.68425 (9)0.43354 (9)0.0316 (4)
O50.52767 (15)0.59208 (9)0.57875 (9)0.0316 (4)
H50.572 (2)0.6279 (13)0.5551 (15)0.047*
O60.39596 (15)0.60645 (9)0.47430 (9)0.0302 (4)
O70.13511 (15)0.61815 (9)0.55937 (9)0.0329 (4)
O80.06732 (15)0.56926 (10)0.44624 (9)0.0298 (4)
H80.022 (3)0.6127 (15)0.4416 (15)0.045*
O90.01165 (15)0.54289 (9)0.91554 (9)0.0291 (4)
O100.13307 (16)0.55344 (10)1.02487 (9)0.0319 (4)
H100.078 (2)0.5177 (13)1.0442 (15)0.048*
O110.38062 (15)0.52336 (9)0.94221 (9)0.0314 (4)
O120.47862 (16)0.59219 (10)1.03214 (10)0.0334 (4)
H120.529 (3)0.5553 (13)1.0388 (17)0.050*
C10.7758 (2)0.86243 (13)0.23578 (13)0.0286 (6)
H1A0.83360.82100.23220.034*
H1B0.69630.85080.20630.034*
C20.8377 (2)0.92728 (13)0.19892 (13)0.0303 (6)
H2A0.92060.93650.22580.036*
H2B0.85360.91740.14280.036*
C30.7543 (2)0.99311 (13)0.20515 (13)0.0283 (6)
H3A0.67520.98600.17340.034*
H3B0.79941.03480.18360.034*
C40.7209 (2)1.00790 (13)0.29086 (13)0.0300 (6)
H4A0.79891.02110.32120.036*
H4B0.66111.04850.29280.036*
C50.6608 (2)0.94265 (12)0.32821 (13)0.0290 (6)
H5A0.57800.93280.30150.035*
H5B0.64480.95270.38430.035*
C60.7462 (2)0.87649 (12)0.32232 (12)0.0232 (5)
H60.82770.88590.35200.028*
C70.6815 (2)0.81489 (12)0.35909 (12)0.0224 (5)
H70.60670.79840.33250.027*
C80.7153 (2)0.77971 (12)0.42489 (12)0.0217 (5)
C90.6326 (2)0.72300 (12)0.45483 (12)0.0233 (5)
C100.8316 (2)0.79437 (12)0.47521 (13)0.0256 (5)
H10A0.87850.83480.45230.031*
H10B0.80500.80880.52840.031*
C110.9193 (2)0.73159 (13)0.48279 (13)0.0258 (5)
C120.1708 (2)0.47583 (12)0.72032 (13)0.0254 (5)
H12A0.20030.51180.75930.030*
H12B0.11970.50060.67900.030*
C130.0883 (2)0.42064 (14)0.76085 (14)0.0316 (6)
H13A0.01630.44500.78590.038*
H13B0.05310.38710.72100.038*
C140.1639 (2)0.37941 (14)0.82281 (13)0.0319 (6)
H14A0.10940.34180.84510.038*
H14B0.18990.41200.86610.038*
C150.2816 (2)0.34522 (13)0.78859 (14)0.0342 (6)
H15A0.25540.30750.75080.041*
H15B0.33270.32270.83150.041*
C160.3624 (2)0.40022 (13)0.74674 (14)0.0300 (6)
H16A0.43510.37590.72230.036*
H16B0.39690.43480.78580.036*
C170.2857 (2)0.44026 (12)0.68315 (12)0.0221 (5)
H170.25360.40470.64360.026*
C180.3650 (2)0.49360 (12)0.64108 (12)0.0210 (5)
H180.44160.50810.66700.025*
C190.3392 (2)0.52292 (12)0.57084 (12)0.0220 (5)
C200.4251 (2)0.57730 (12)0.53837 (12)0.0218 (5)
C210.2249 (2)0.50708 (12)0.51964 (13)0.0241 (5)
H21A0.17690.46720.54290.029*
H21B0.25290.49180.46700.029*
C220.1394 (2)0.57048 (13)0.51064 (12)0.0245 (5)
C230.1341 (2)0.74770 (13)0.74597 (15)0.0337 (6)
H23A0.09350.71470.70740.040*
H23B0.06620.77030.77660.040*
C240.2075 (3)0.80494 (14)0.70232 (16)0.0406 (7)
H24A0.14940.82930.66430.049*
H24B0.23960.84090.74050.049*
C250.3181 (2)0.77368 (15)0.65866 (14)0.0392 (7)
H25A0.28500.74380.61470.047*
H25B0.36830.81290.63590.047*
C260.4034 (2)0.72914 (14)0.71173 (14)0.0330 (6)
H26A0.44660.76040.75100.040*
H26B0.46950.70620.67990.040*
C270.3288 (2)0.67178 (13)0.75447 (14)0.0279 (6)
H27A0.38680.64490.79040.033*
H27B0.29170.63790.71560.033*
C280.2228 (2)0.70562 (12)0.80172 (12)0.0232 (5)
H280.26240.73980.84030.028*
C290.1525 (2)0.65043 (12)0.84662 (12)0.0227 (5)
H290.07540.63340.82330.027*
C300.1871 (2)0.62253 (12)0.91624 (12)0.0222 (5)
C310.1035 (2)0.56922 (12)0.95195 (12)0.0214 (5)
C320.3049 (2)0.64220 (13)0.96253 (13)0.0258 (5)
H32A0.28060.66301.01360.031*
H32B0.35200.67900.93330.031*
C330.3907 (2)0.57935 (13)0.97767 (12)0.0247 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0250 (9)0.0345 (11)0.0316 (9)−0.0096 (8)−0.0043 (8)0.0093 (8)
O20.0306 (10)0.0391 (11)0.0297 (8)−0.0028 (8)−0.0050 (8)0.0159 (8)
O30.0440 (12)0.0446 (12)0.0337 (9)0.0166 (9)−0.0211 (9)−0.0119 (9)
O40.0300 (10)0.0369 (11)0.0275 (8)0.0057 (8)−0.0083 (8)−0.0069 (8)
O50.0248 (10)0.0374 (11)0.0323 (9)−0.0098 (8)−0.0041 (8)0.0096 (8)
O60.0281 (9)0.0362 (10)0.0262 (8)−0.0030 (8)−0.0017 (7)0.0101 (7)
O70.0321 (10)0.0372 (11)0.0288 (8)0.0094 (8)−0.0097 (8)−0.0087 (8)
O80.0272 (9)0.0369 (11)0.0246 (8)0.0041 (8)−0.0087 (7)−0.0017 (7)
O90.0263 (9)0.0322 (10)0.0286 (8)−0.0066 (8)−0.0060 (8)0.0064 (7)
O100.0312 (10)0.0412 (11)0.0231 (8)−0.0089 (8)−0.0023 (7)0.0107 (7)
O110.0306 (10)0.0321 (10)0.0312 (8)0.0027 (8)−0.0079 (8)−0.0075 (8)
O120.0295 (10)0.0379 (11)0.0321 (9)0.0044 (8)−0.0141 (8)−0.0088 (8)
C10.0292 (13)0.0280 (14)0.0286 (12)−0.0017 (11)0.0026 (11)0.0027 (10)
C20.0317 (14)0.0348 (15)0.0245 (11)−0.0047 (11)0.0027 (11)0.0037 (10)
C30.0277 (13)0.0287 (14)0.0284 (12)−0.0051 (10)−0.0045 (11)0.0075 (10)
C40.0319 (14)0.0266 (14)0.0316 (12)−0.0028 (11)0.0041 (11)0.0023 (10)
C50.0299 (13)0.0279 (14)0.0296 (12)−0.0028 (11)0.0057 (11)0.0050 (10)
C60.0201 (12)0.0248 (13)0.0246 (11)−0.0032 (10)−0.0011 (10)0.0063 (10)
C70.0181 (12)0.0259 (13)0.0231 (11)−0.0026 (10)−0.0025 (10)0.0020 (10)
C80.0212 (12)0.0224 (12)0.0215 (10)0.0004 (9)−0.0011 (10)0.0026 (9)
C90.0213 (13)0.0263 (13)0.0222 (11)−0.0002 (10)−0.0013 (10)0.0009 (10)
C100.0283 (13)0.0255 (14)0.0228 (11)−0.0017 (10)−0.0040 (10)0.0032 (10)
C110.0229 (13)0.0318 (14)0.0225 (11)−0.0025 (10)−0.0019 (10)0.0027 (10)
C120.0252 (13)0.0252 (13)0.0258 (11)0.0033 (10)0.0013 (10)0.0053 (10)
C130.0259 (13)0.0401 (16)0.0292 (12)−0.0020 (11)0.0049 (11)0.0071 (11)
C140.0338 (14)0.0357 (15)0.0262 (12)−0.0073 (11)0.0027 (11)0.0068 (11)
C150.0406 (15)0.0293 (14)0.0325 (13)0.0038 (12)−0.0004 (12)0.0100 (11)
C160.0286 (14)0.0307 (14)0.0307 (12)0.0042 (11)0.0028 (11)0.0063 (11)
C170.0244 (12)0.0190 (12)0.0228 (10)−0.0013 (9)0.0009 (10)−0.0001 (9)
C180.0171 (11)0.0229 (13)0.0231 (11)0.0008 (9)−0.0010 (9)−0.0024 (9)
C190.0204 (12)0.0216 (12)0.0242 (11)0.0035 (9)0.0021 (10)0.0005 (9)
C200.0176 (12)0.0255 (13)0.0223 (11)0.0025 (9)−0.0010 (10)−0.0001 (9)
C210.0237 (12)0.0253 (13)0.0232 (11)−0.0025 (10)0.0012 (10)0.0009 (9)
C220.0203 (12)0.0314 (14)0.0218 (11)−0.0025 (10)0.0017 (10)0.0029 (10)
C230.0331 (14)0.0282 (14)0.0398 (14)0.0045 (11)0.0011 (12)0.0126 (11)
C240.0395 (16)0.0344 (16)0.0474 (15)−0.0022 (13)−0.0086 (13)0.0212 (13)
C250.0419 (16)0.0454 (17)0.0299 (13)−0.0208 (13)−0.0069 (12)0.0131 (12)
C260.0290 (14)0.0380 (16)0.0321 (13)−0.0052 (11)0.0036 (12)0.0040 (11)
C270.0245 (13)0.0267 (14)0.0325 (12)0.0002 (10)0.0005 (11)0.0031 (10)
C280.0277 (13)0.0222 (13)0.0197 (10)−0.0035 (10)−0.0023 (10)0.0008 (9)
C290.0236 (12)0.0221 (13)0.0223 (11)−0.0002 (10)−0.0001 (10)−0.0022 (9)
C300.0236 (12)0.0213 (12)0.0217 (10)0.0019 (10)0.0013 (10)0.0003 (9)
C310.0199 (12)0.0252 (13)0.0190 (10)0.0026 (10)−0.0008 (10)0.0019 (9)
C320.0286 (13)0.0275 (14)0.0213 (11)−0.0037 (10)−0.0022 (10)0.0013 (10)
C330.0201 (12)0.0345 (15)0.0196 (10)−0.0031 (10)0.0017 (10)0.0015 (10)

Geometric parameters (Å, °)

O1—C91.292 (3)C13—C141.516 (3)
O1—H10.93 (2)C13—H13A0.9900
O2—C91.252 (3)C13—H13B0.9900
O3—C111.306 (3)C14—C151.524 (3)
O3—H30.90 (2)C14—H14A0.9900
O4—C111.222 (3)C14—H14B0.9900
O5—C201.295 (3)C15—C161.525 (3)
O5—H50.92 (2)C15—H15A0.9900
O6—C201.249 (3)C15—H15B0.9900
O7—C221.220 (3)C16—C171.530 (3)
O8—C221.316 (3)C16—H16A0.9900
O8—H80.95 (3)C16—H16B0.9900
O9—C311.238 (3)C17—C181.496 (3)
O10—C311.303 (3)C17—H171.0000
O10—H100.95 (2)C18—C191.335 (3)
O11—C331.214 (3)C18—H180.9500
O12—C331.315 (3)C19—C201.479 (3)
O12—H120.87 (2)C19—C211.497 (3)
C1—C21.522 (3)C21—C221.498 (3)
C1—C61.533 (3)C21—H21A0.9900
C1—H1A0.9900C21—H21B0.9900
C1—H1B0.9900C23—C241.526 (3)
C2—C31.520 (3)C23—C281.533 (3)
C2—H2A0.9900C23—H23A0.9900
C2—H2B0.9900C23—H23B0.9900
C3—C41.531 (3)C24—C251.514 (4)
C3—H3A0.9900C24—H24A0.9900
C3—H3B0.9900C24—H24B0.9900
C4—C51.524 (3)C25—C261.509 (4)
C4—H4A0.9900C25—H25A0.9900
C4—H4B0.9900C25—H25B0.9900
C5—C61.538 (3)C26—C271.526 (3)
C5—H5A0.9900C26—H26A0.9900
C5—H5B0.9900C26—H26B0.9900
C6—C71.487 (3)C27—C281.529 (3)
C6—H61.0000C27—H27A0.9900
C7—C81.338 (3)C27—H27B0.9900
C7—H70.9500C28—C291.493 (3)
C8—C91.474 (3)C28—H281.0000
C8—C101.502 (3)C29—C301.335 (3)
C10—C111.500 (3)C29—H290.9500
C10—H10A0.9900C30—C311.472 (3)
C10—H10B0.9900C30—C321.499 (3)
C12—C131.526 (3)C32—C331.504 (3)
C12—C171.532 (3)C32—H32A0.9900
C12—H12A0.9900C32—H32B0.9900
C12—H12B0.9900
C9—O1—H1111.1 (17)C15—C16—C17111.7 (2)
C11—O3—H3108 (2)C15—C16—H16A109.3
C20—O5—H5110.8 (18)C17—C16—H16A109.3
C22—O8—H8109.4 (17)C15—C16—H16B109.3
C31—O10—H10110.7 (17)C17—C16—H16B109.3
C33—O12—H12111 (2)H16A—C16—H16B107.9
C2—C1—C6110.85 (19)C18—C17—C16112.02 (19)
C2—C1—H1A109.5C18—C17—C12111.17 (18)
C6—C1—H1A109.5C16—C17—C12109.38 (17)
C2—C1—H1B109.5C18—C17—H17108.0
C6—C1—H1B109.5C16—C17—H17108.0
H1A—C1—H1B108.1C12—C17—H17108.0
C3—C2—C1111.55 (19)C19—C18—C17126.8 (2)
C3—C2—H2A109.3C19—C18—H18116.6
C1—C2—H2A109.3C17—C18—H18116.6
C3—C2—H2B109.3C18—C19—C20120.3 (2)
C1—C2—H2B109.3C18—C19—C21125.4 (2)
H2A—C2—H2B108.0C20—C19—C21114.26 (19)
C2—C3—C4111.1 (2)O6—C20—O5123.4 (2)
C2—C3—H3A109.4O6—C20—C19119.2 (2)
C4—C3—H3A109.4O5—C20—C19117.40 (19)
C2—C3—H3B109.4C19—C21—C22111.99 (19)
C4—C3—H3B109.4C19—C21—H21A109.2
H3A—C3—H3B108.0C22—C21—H21A109.2
C5—C4—C3111.0 (2)C19—C21—H21B109.2
C5—C4—H4A109.4C22—C21—H21B109.2
C3—C4—H4A109.4H21A—C21—H21B107.9
C5—C4—H4B109.4O7—C22—O8123.1 (2)
C3—C4—H4B109.4O7—C22—C21123.0 (2)
H4A—C4—H4B108.0O8—C22—C21113.8 (2)
C4—C5—C6111.80 (18)C24—C23—C28110.8 (2)
C4—C5—H5A109.3C24—C23—H23A109.5
C6—C5—H5A109.3C28—C23—H23A109.5
C4—C5—H5B109.3C24—C23—H23B109.5
C6—C5—H5B109.3C28—C23—H23B109.5
H5A—C5—H5B107.9H23A—C23—H23B108.1
C7—C6—C1112.03 (19)C25—C24—C23111.7 (2)
C7—C6—C5108.97 (17)C25—C24—H24A109.3
C1—C6—C5109.54 (19)C23—C24—H24A109.3
C7—C6—H6108.7C25—C24—H24B109.3
C1—C6—H6108.7C23—C24—H24B109.3
C5—C6—H6108.7H24A—C24—H24B107.9
C8—C7—C6128.2 (2)C26—C25—C24112.1 (2)
C8—C7—H7115.9C26—C25—H25A109.2
C6—C7—H7115.9C24—C25—H25A109.2
C7—C8—C9119.8 (2)C26—C25—H25B109.2
C7—C8—C10125.5 (2)C24—C25—H25B109.2
C9—C8—C10114.64 (19)H25A—C25—H25B107.9
O2—C9—O1123.1 (2)C25—C26—C27111.6 (2)
O2—C9—C8118.9 (2)C25—C26—H26A109.3
O1—C9—C8118.0 (2)C27—C26—H26A109.3
C11—C10—C8113.3 (2)C25—C26—H26B109.3
C11—C10—H10A108.9C27—C26—H26B109.3
C8—C10—H10A108.9H26A—C26—H26B108.0
C11—C10—H10B108.9C26—C27—C28110.34 (19)
C8—C10—H10B108.9C26—C27—H27A109.6
H10A—C10—H10B107.7C28—C27—H27A109.6
O4—C11—O3123.6 (2)C26—C27—H27B109.6
O4—C11—C10123.0 (2)C28—C27—H27B109.6
O3—C11—C10113.3 (2)H27A—C27—H27B108.1
C13—C12—C17110.75 (19)C29—C28—C27110.96 (18)
C13—C12—H12A109.5C29—C28—C23111.73 (19)
C17—C12—H12A109.5C27—C28—C23109.36 (18)
C13—C12—H12B109.5C29—C28—H28108.2
C17—C12—H12B109.5C27—C28—H28108.2
H12A—C12—H12B108.1C23—C28—H28108.2
C14—C13—C12111.4 (2)C30—C29—C28126.6 (2)
C14—C13—H13A109.3C30—C29—H29116.7
C12—C13—H13A109.3C28—C29—H29116.7
C14—C13—H13B109.3C29—C30—C31118.6 (2)
C12—C13—H13B109.3C29—C30—C32124.9 (2)
H13A—C13—H13B108.0C31—C30—C32116.53 (19)
C13—C14—C15111.59 (18)O9—C31—O10123.3 (2)
C13—C14—H14A109.3O9—C31—C30122.18 (19)
C15—C14—H14A109.3O10—C31—C30114.5 (2)
C13—C14—H14B109.3C30—C32—C33112.5 (2)
C15—C14—H14B109.3C30—C32—H32A109.1
H14A—C14—H14B108.0C33—C32—H32A109.1
C14—C15—C16111.2 (2)C30—C32—H32B109.1
C14—C15—H15A109.4C33—C32—H32B109.1
C16—C15—H15A109.4H32A—C32—H32B107.8
C14—C15—H15B109.4O11—C33—O12124.0 (2)
C16—C15—H15B109.4O11—C33—C32123.3 (2)
H15A—C15—H15B108.0O12—C33—C32112.7 (2)
C6—C1—C2—C3−57.4 (3)C17—C18—C19—C20177.59 (19)
C1—C2—C3—C455.7 (3)C17—C18—C19—C21−0.7 (4)
C2—C3—C4—C5−54.5 (3)C18—C19—C20—O6−176.6 (2)
C3—C4—C5—C655.6 (3)C21—C19—C20—O61.9 (3)
C2—C1—C6—C7177.96 (19)C18—C19—C20—O53.4 (3)
C2—C1—C6—C556.9 (3)C21—C19—C20—O5−178.14 (18)
C4—C5—C6—C7−179.48 (19)C18—C19—C21—C22114.2 (2)
C4—C5—C6—C1−56.6 (3)C20—C19—C21—C22−64.2 (2)
C1—C6—C7—C8125.9 (2)C19—C21—C22—O7−25.6 (3)
C5—C6—C7—C8−112.7 (3)C19—C21—C22—O8155.81 (18)
C6—C7—C8—C9175.5 (2)C28—C23—C24—C2555.4 (3)
C6—C7—C8—C10−2.1 (4)C23—C24—C25—C26−53.0 (3)
C7—C8—C9—O2−178.8 (2)C24—C25—C26—C2753.8 (3)
C10—C8—C9—O2−0.9 (3)C25—C26—C27—C28−56.9 (3)
C7—C8—C9—O10.9 (3)C26—C27—C28—C29−177.58 (19)
C10—C8—C9—O1178.79 (19)C26—C27—C28—C2358.7 (3)
C7—C8—C10—C11−120.5 (2)C24—C23—C28—C29178.6 (2)
C9—C8—C10—C1161.8 (2)C24—C23—C28—C27−58.2 (3)
C8—C10—C11—O425.3 (3)C27—C28—C29—C3082.5 (3)
C8—C10—C11—O3−156.38 (19)C23—C28—C29—C30−155.2 (2)
C17—C12—C13—C1457.2 (3)C28—C29—C30—C31179.0 (2)
C12—C13—C14—C15−54.9 (3)C28—C29—C30—C320.1 (4)
C13—C14—C15—C1653.7 (3)C29—C30—C31—O99.4 (3)
C14—C15—C16—C17−55.4 (3)C32—C30—C31—O9−171.6 (2)
C15—C16—C17—C18−179.20 (19)C29—C30—C31—O10−169.4 (2)
C15—C16—C17—C1257.1 (3)C32—C30—C31—O109.7 (3)
C13—C12—C17—C18178.21 (19)C29—C30—C32—C33−120.9 (2)
C13—C12—C17—C16−57.6 (3)C31—C30—C32—C3360.1 (2)
C16—C17—C18—C19160.7 (2)C30—C32—C33—O1115.5 (3)
C12—C17—C18—C19−76.6 (3)C30—C32—C33—O12−165.74 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O12—H12···O11i0.87 (2)1.78 (2)2.656 (2)175 (3)
O10—H10···O9ii0.95 (2)1.63 (2)2.586 (2)175 (3)
O8—H8···O4iii0.95 (3)1.70 (3)2.642 (2)172 (3)
O5—H5···O20.92 (2)1.68 (2)2.594 (2)175 (3)
O3—H3···O7iv0.90 (2)1.75 (2)2.644 (2)173 (3)
O1—H1···O60.93 (2)1.66 (2)2.591 (2)175 (3)

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+1, −z+2; (iii) x−1, y, z; (iv) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2033).

References

  • Bruker (1997). SHELXTL Bruker AXS Inc., Madison, Wisconsin, USA.
  • Rigaku/MSC (2005). CrystalClear Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Stobbe, H. (1893). Ber. Dtsch. Chem. Ges.26, 2312.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography