organic papers
o2064
Andrew D. Bond C7H16O doi:10.1107/S1600536806013936 Acta Cryst.(2006). E62, o2064–o2065 Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
3-Ethylpentan-3-ol
Andrew D. Bond
University of Southern Denmark, Department of Chemistry, Campusvej 55, 5230 Odense M, Denmark
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study T= 150 K
Mean(C–C) = 0.002 A˚ Rfactor = 0.044 wRfactor = 0.117
Data-to-parameter ratio = 19.2
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 17 April 2006 Accepted 18 April 2006
#2006 International Union of Crystallography All rights reserved
The crystal structure of the title compound, C7H16O, has been
determined at 150 (2) K followingin situcrystal growth from the liquid. The structure contains four independent molecules in the asymmetric unit, forming a fourfold cyclic arrangement
viaO—H O hydrogen bonds.
Comment
Just over a decade ago, Brock & Duncan (1994) noted that monoalcohols commonly crystallize in high-symmetry space groups (tetragonal, trigonal, hexagonal and cubic groups) or with more than one independent molecule in the asymmetric unit (Z0> 1). This can be rationalized by considering that the
geometrical features of extended O—H O hydrogen-bond
motifs are rarely compatible with efficient packing of the molecules about 21 screw axes or glide planes, or by simple
translation. The crystal structure of the title compound, (I), is
a typical example; the asymmetric unit in space group P1
comprises a fourfold cyclic arrangement formed via O—
H O hydrogen bonds (Fig. 1 and Table 1). These units are arranged in approximate hexagonal close-packed layers, which stack directly one upon the other to form a simple hexagonal arrangement in three dimensions (Fig. 2).
Experimental
Compound (I) (98%) was obtained from the Aldrich Company and was used without further purification. The crystal was grown in a 0.4 mm glass capillary tube using a technique described previously (Davies & Bond, 2001), atca258 K (a temperature only slightly less than the melting point of the solid in the capillary tube). Once formed, the crystal was cooled slowly to 150 K for data collection. The length of the cylindrical crystal could not be estimated accurately, but it exceeded the diameter of the collimator (0.60 mm).
Crystal data
C7H16O Mr= 116.20
Triclinic,P1
a= 10.5552 (10) A˚
b= 11.2140 (9) A˚
c= 14.1681 (13) A˚
= 88.682 (3)
= 72.512 (3)
= 76.904 (4)
V= 1556.1 (2) A˚3 Z= 8
Dx= 0.992 Mg m
3
MoKradiation
Data collection
Bruker–Nonius X8APEX-II CCD diffractometer
!and’scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2003); ratio of minimum to maximum
apparent transmission: 0.711045
Tmin= 0.693,Tmax= 0.975
35248 measured reflections 5870 independent reflections 4402 reflections withI> 2(I)
Rint= 0.049
max= 25.8
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.044 wR(F2) = 0.117
S= 1.03 5870 reflections 305 parameters
H atoms treated by a mixture of independent and constrained refinement
w= 1/[2
(Fo2) + (0.0499P)2
+ 0.3995P]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001
max= 0.23 e A˚
3
min=0.19 e A˚
3
Table 1
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
O1—H1 O4 0.84 (2) 1.98 (2) 2.7977 (16) 167.7 (18) O2—H2 O1 0.86 (2) 1.93 (2) 2.7686 (14) 165.8 (17) O3—H3 O2 0.87 (2) 1.92 (2) 2.7759 (15) 169.4 (18) O4—H4 O3 0.81 (2) 2.01 (2) 2.7888 (15) 160.5 (18)
H atoms bound to C atoms were positioned geometrically and allowed to ride during subsequent refinement, with C—H = 0.99 A˚ and Uiso(H) = 1.2Ueq(C) for the methylene groups, and C—H =
0.98 A˚ andUiso(H) = 1.5Ueq(C) for the methyl groups. The H atoms
of the hydroxy groups were located in difference Fourier maps and refined without restraint, employing isotropic displacement para-meters.
Data collection:APEX2(Bruker Nonius, 2004); cell refinement:
SAINT(Bruker, 2003); data reduction:SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; soft-ware used to prepare material for publication:SHELXTL.
I am grateful to the Danish Natural Science Research Council (SNF) and Carlsbergfondet for provision of the X-ray equipment, and to SNF for fundingviaa STENO stipend (21-03-0164).
References
Brock, C. P. & Duncan, L. L. (1994).Chem. Mater.6, 1307–1312.
Bruker (2003).SAINT. Version 7.06a. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker Nonius (2004).APEX2. Version 1.0-22. Bruker Nonius BV, Delft, The Netherlands.
Davies, J. E. & Bond, A. D. (2001).Acta Cryst.E57, o947–o949.
Sheldrick, G. M. (2000).SHELXTL. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA.
[image:2.610.322.553.69.247.2]Sheldrick, G. M. (2003).SADABS. Version 2.10. Bruker AXS Inc., Madison, Wisconsin, USA.
Figure 1
[image:2.610.83.259.74.257.2]The asymmetric unit, showing displacement ellipsoids at the 50% probability level. H atoms bound to C atoms have been omitted. Dashed lines denote O—H O hydrogen bonds.
Figure 2
supporting information
sup-1 Acta Cryst. (2006). E62, o2064–o2065
supporting information
Acta Cryst. (2006). E62, o2064–o2065 [https://doi.org/10.1107/S1600536806013936]
3-Ethylpentan-3-ol
Andrew D. Bond
3-ethyl-3-pentanol
Crystal data
C7H16O
Mr = 116.20
Triclinic, P1
Hall symbol: -P 1
a = 10.5552 (10) Å
b = 11.2140 (9) Å
c = 14.1681 (13) Å
α = 88.682 (3)°
β = 72.512 (3)°
γ = 76.904 (4)°
V = 1556.1 (2) Å3
Z = 8
F(000) = 528
Dx = 0.992 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 5406 reflections
θ = 2.2–25.7°
µ = 0.06 mm−1
T = 150 K
Cylinder, colourless 0.60 × 0.20 (radius) mm
Data collection
Bruker–Nonius X8APEX-II CCD diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω and φ scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003); ratio of minimum to maximum apparent transmission: 0.711045
Tmin = 0.693, Tmax = 0.975
35248 measured reflections 5870 independent reflections 4402 reflections with I > 2σ(I)
Rint = 0.049
θmax = 25.8°, θmin = 3.6°
h = −12→12
k = −13→13
l = −17→16
Refinement
Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.044
wR(F2) = 0.117
S = 1.03
5870 reflections 305 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(F
o2) + (0.0499P)2 + 0.3995P]
where P = (Fo2 + 2Fc2)/3 (Δ/σ)max < 0.001
Δρmax = 0.23 e Å−3
Special details
Experimental. Grown in situ in 0.4 mm o.d. capillary at 258 K.
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)
x y z Uiso*/Ueq
O1 0.40289 (12) 0.90260 (9) 0.77740 (7) 0.0315 (2)
H1 0.488 (2) 0.8898 (17) 0.7602 (14) 0.053 (6)*
C1 0.34684 (14) 0.99578 (13) 0.85685 (11) 0.0298 (3)
C11 0.19371 (14) 1.02633 (14) 0.87228 (11) 0.0334 (3)
H11A 0.1773 1.0547 0.8094 0.040*
H11B 0.1602 0.9503 0.8877 0.040*
C12 0.11041 (17) 1.12344 (17) 0.95413 (14) 0.0504 (5)
H12A 0.0135 1.1369 0.9594 0.076*
H12B 0.1401 1.2002 0.9385 0.076*
H12C 0.1241 1.0957 1.0172 0.076*
C13 0.38380 (17) 0.94505 (16) 0.94897 (12) 0.0428 (4)
H13A 0.4845 0.9206 0.9317 0.051*
H13B 0.3518 1.0122 1.0007 0.051*
C14 0.3269 (2) 0.83686 (17) 0.99320 (13) 0.0529 (5)
H14A 0.3563 0.8127 1.0516 0.079*
H14B 0.3606 0.7680 0.9440 0.079*
H14C 0.2270 0.8599 1.0126 0.079*
C15 0.41021 (17) 1.10562 (14) 0.82482 (14) 0.0461 (4)
H15A 0.3728 1.1689 0.8798 0.055*
H15B 0.5098 1.0790 0.8139 0.055*
C16 0.38705 (19) 1.16378 (16) 0.73209 (16) 0.0631 (6)
H16A 0.4306 1.2334 0.7178 0.095*
H16B 0.2888 1.1924 0.7422 0.095*
H16C 0.4268 1.1032 0.6762 0.095*
O2 0.38796 (10) 0.65997 (10) 0.76864 (7) 0.0297 (2)
H2 0.3789 (18) 0.7372 (18) 0.7787 (13) 0.052 (5)*
C2 0.29072 (13) 0.64111 (12) 0.72043 (10) 0.0253 (3)
C21 0.34258 (15) 0.50924 (13) 0.67860 (12) 0.0331 (3)
H21A 0.3451 0.4544 0.7341 0.040*
H21B 0.4374 0.4991 0.6346 0.040*
C22 0.25841 (17) 0.46803 (15) 0.62060 (12) 0.0396 (4)
H22A 0.2990 0.3825 0.5966 0.059*
H22B 0.2573 0.5199 0.5641 0.059*
supporting information
sup-3 Acta Cryst. (2006). E62, o2064–o2065
C23 0.15020 (15) 0.66230 (14) 0.79861 (11) 0.0322 (3)
H23A 0.1239 0.7485 0.8245 0.039*
H23B 0.0828 0.6511 0.7657 0.039*
C24 0.14012 (19) 0.57976 (17) 0.88572 (12) 0.0484 (4)
H24A 0.0470 0.6006 0.9314 0.073*
H24B 0.2044 0.5914 0.9203 0.073*
H24C 0.1625 0.4940 0.8616 0.073*
C25 0.28532 (15) 0.73408 (14) 0.64017 (11) 0.0318 (3)
H25A 0.2180 0.7209 0.6080 0.038*
H25B 0.2520 0.8175 0.6723 0.038*
C26 0.42064 (18) 0.72830 (18) 0.56046 (12) 0.0469 (4)
H26A 0.4080 0.7906 0.5124 0.070*
H26B 0.4535 0.6469 0.5266 0.070*
H26C 0.4877 0.7437 0.5910 0.070*
O3 0.66917 (11) 0.58633 (9) 0.72772 (7) 0.0311 (2)
H3 0.581 (2) 0.5997 (17) 0.7388 (14) 0.053 (6)*
C3 0.71170 (14) 0.48503 (12) 0.78489 (10) 0.0265 (3)
C31 0.66539 (15) 0.37452 (13) 0.75734 (11) 0.0321 (3)
H31A 0.6916 0.3056 0.7978 0.039*
H31B 0.5645 0.3956 0.7751 0.039*
C32 0.72343 (18) 0.33130 (15) 0.64872 (12) 0.0417 (4)
H32A 0.6879 0.2610 0.6378 0.063*
H32B 0.8232 0.3070 0.6306 0.063*
H32C 0.6965 0.3980 0.6077 0.063*
C33 0.86688 (14) 0.46344 (13) 0.75528 (11) 0.0307 (3)
H33A 0.9041 0.4479 0.6826 0.037*
H33B 0.8906 0.5392 0.7718 0.037*
C34 0.93606 (16) 0.35711 (15) 0.80487 (13) 0.0437 (4)
H34A 1.0350 0.3494 0.7819 0.066*
H34B 0.9154 0.2810 0.7877 0.066*
H34C 0.9022 0.3726 0.8769 0.066*
C35 0.64336 (16) 0.51971 (14) 0.89532 (11) 0.0362 (4)
H35A 0.5432 0.5391 0.9082 0.043*
H35B 0.6671 0.4473 0.9333 0.043*
C36 0.6810 (2) 0.62704 (17) 0.93451 (13) 0.0518 (5)
H36A 0.6319 0.6423 1.0053 0.078*
H36B 0.6560 0.7001 0.8988 0.078*
H36C 0.7795 0.6081 0.9247 0.078*
O4 0.68743 (11) 0.82986 (10) 0.70223 (8) 0.0378 (3)
H4 0.7007 (18) 0.7555 (18) 0.7003 (13) 0.047 (5)*
C4 0.78629 (14) 0.87387 (12) 0.62269 (11) 0.0292 (3)
C41 0.92051 (14) 0.77709 (12) 0.59159 (11) 0.0301 (3)
H41A 0.9924 0.8160 0.5502 0.036*
H41B 0.9458 0.7505 0.6519 0.036*
C42 0.92080 (17) 0.66394 (14) 0.53459 (12) 0.0396 (4)
H42A 1.0110 0.6078 0.5188 0.059*
H42B 0.8998 0.6882 0.4731 0.059*
C43 0.72389 (16) 0.90298 (15) 0.53814 (13) 0.0425 (4)
H43A 0.6372 0.9655 0.5631 0.051*
H43B 0.7014 0.8279 0.5188 0.051*
C44 0.8139 (2) 0.94965 (18) 0.44555 (14) 0.0573 (5)
H44A 0.7659 0.9651 0.3955 0.086*
H44B 0.8994 0.8878 0.4189 0.086*
H44C 0.8342 1.0259 0.4629 0.086*
C45 0.80438 (17) 0.99005 (14) 0.66552 (13) 0.0424 (4)
H45A 0.8663 1.0269 0.6122 0.051*
H45B 0.7147 1.0492 0.6864 0.051*
C46 0.8607 (2) 0.97319 (19) 0.75291 (14) 0.0628 (6)
H46A 0.8679 1.0527 0.7753 0.094*
H46B 0.9513 0.9174 0.7327 0.094*
H46C 0.7994 0.9386 0.8071 0.094*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
O1 0.0303 (6) 0.0278 (5) 0.0322 (6) −0.0060 (4) −0.0034 (5) −0.0066 (4)
C1 0.0257 (8) 0.0273 (7) 0.0327 (8) −0.0057 (6) −0.0029 (6) −0.0092 (6)
C11 0.0265 (8) 0.0367 (8) 0.0351 (8) −0.0081 (6) −0.0062 (6) 0.0022 (7)
C12 0.0323 (9) 0.0503 (10) 0.0532 (11) 0.0023 (8) 0.0014 (8) −0.0036 (9)
C13 0.0316 (9) 0.0560 (10) 0.0388 (9) −0.0024 (7) −0.0123 (7) −0.0141 (8)
C14 0.0586 (12) 0.0625 (12) 0.0329 (9) −0.0048 (9) −0.0140 (8) 0.0081 (8)
C15 0.0339 (9) 0.0324 (9) 0.0615 (11) −0.0121 (7) 0.0057 (8) −0.0159 (8)
C16 0.0469 (11) 0.0330 (9) 0.0889 (15) −0.0095 (8) 0.0091 (10) 0.0136 (9)
O2 0.0303 (6) 0.0266 (6) 0.0365 (6) −0.0073 (4) −0.0155 (5) −0.0004 (4)
C2 0.0221 (7) 0.0272 (7) 0.0283 (7) −0.0067 (6) −0.0092 (6) 0.0002 (6)
C21 0.0305 (8) 0.0300 (8) 0.0392 (8) −0.0061 (6) −0.0113 (7) −0.0039 (7)
C22 0.0408 (9) 0.0403 (9) 0.0402 (9) −0.0140 (7) −0.0119 (7) −0.0067 (7)
C23 0.0293 (8) 0.0365 (8) 0.0312 (8) −0.0106 (6) −0.0074 (6) 0.0003 (6)
C24 0.0531 (11) 0.0619 (11) 0.0336 (9) −0.0272 (9) −0.0084 (8) 0.0094 (8)
C25 0.0321 (8) 0.0344 (8) 0.0316 (8) −0.0114 (6) −0.0113 (6) 0.0052 (6)
C26 0.0466 (10) 0.0655 (11) 0.0328 (9) −0.0287 (9) −0.0071 (8) 0.0088 (8)
O3 0.0265 (6) 0.0279 (5) 0.0344 (6) −0.0045 (4) −0.0046 (5) 0.0107 (4)
C3 0.0245 (7) 0.0266 (7) 0.0252 (7) −0.0050 (6) −0.0039 (6) 0.0073 (6)
C31 0.0306 (8) 0.0309 (8) 0.0356 (8) −0.0100 (6) −0.0099 (7) 0.0114 (6)
C32 0.0524 (10) 0.0349 (8) 0.0397 (9) −0.0107 (7) −0.0162 (8) 0.0016 (7)
C33 0.0256 (8) 0.0328 (8) 0.0307 (8) −0.0063 (6) −0.0044 (6) 0.0037 (6)
C34 0.0319 (9) 0.0479 (10) 0.0489 (10) −0.0026 (7) −0.0140 (8) 0.0098 (8)
C35 0.0311 (8) 0.0421 (9) 0.0282 (8) −0.0041 (7) −0.0019 (6) 0.0037 (7)
C36 0.0572 (12) 0.0521 (11) 0.0401 (10) −0.0042 (9) −0.0112 (8) −0.0102 (8)
O4 0.0337 (6) 0.0272 (6) 0.0410 (6) −0.0097 (5) 0.0077 (5) 0.0038 (5)
C4 0.0233 (7) 0.0255 (7) 0.0328 (8) −0.0071 (6) 0.0010 (6) 0.0051 (6)
C41 0.0267 (8) 0.0292 (7) 0.0293 (7) −0.0037 (6) −0.0030 (6) 0.0014 (6)
C42 0.0426 (9) 0.0313 (8) 0.0345 (8) −0.0083 (7) 0.0037 (7) −0.0012 (7)
C43 0.0307 (9) 0.0434 (9) 0.0524 (10) −0.0089 (7) −0.0120 (8) 0.0162 (8)
supporting information
sup-5 Acta Cryst. (2006). E62, o2064–o2065
C45 0.0359 (9) 0.0276 (8) 0.0511 (10) −0.0082 (7) 0.0063 (8) −0.0041 (7)
C46 0.0765 (14) 0.0613 (12) 0.0489 (11) −0.0292 (11) −0.0046 (10) −0.0210 (10)
Geometric parameters (Å, º)
O1—C1 1.4431 (17) O3—C3 1.4468 (16)
O1—H1 0.84 (2) O3—H3 0.87 (2)
C1—C11 1.523 (2) C3—C33 1.5262 (19)
C1—C15 1.528 (2) C3—C31 1.529 (2)
C1—C13 1.533 (2) C3—C35 1.530 (2)
C11—C12 1.522 (2) C31—C32 1.520 (2)
C11—H11A 0.990 C31—H31A 0.990
C11—H11B 0.990 C31—H31B 0.990
C12—H12A 0.980 C32—H32A 0.980
C12—H12B 0.980 C32—H32B 0.980
C12—H12C 0.980 C32—H32C 0.980
C13—C14 1.515 (3) C33—C34 1.524 (2)
C13—H13A 0.990 C33—H33A 0.990
C13—H13B 0.990 C33—H33B 0.990
C14—H14A 0.980 C34—H34A 0.980
C14—H14B 0.980 C34—H34B 0.980
C14—H14C 0.980 C34—H34C 0.980
C15—C16 1.514 (3) C35—C36 1.515 (2)
C15—H15A 0.990 C35—H35A 0.990
C15—H15B 0.990 C35—H35B 0.990
C16—H16A 0.980 C36—H36A 0.980
C16—H16B 0.980 C36—H36B 0.980
C16—H16C 0.980 C36—H36C 0.980
O2—C2 1.4460 (16) O4—C4 1.4503 (16)
O2—H2 0.86 (2) O4—H4 0.81 (2)
C2—C21 1.5220 (19) C4—C45 1.523 (2)
C2—C25 1.5300 (19) C4—C41 1.5262 (19)
C2—C23 1.5324 (19) C4—C43 1.528 (2)
C21—C22 1.523 (2) C41—C42 1.519 (2)
C21—H21A 0.990 C41—H41A 0.990
C21—H21B 0.990 C41—H41B 0.990
C22—H22A 0.980 C42—H42A 0.980
C22—H22B 0.980 C42—H42B 0.980
C22—H22C 0.980 C42—H42C 0.980
C23—C24 1.518 (2) C43—C44 1.531 (2)
C23—H23A 0.990 C43—H43A 0.990
C23—H23B 0.990 C43—H43B 0.990
C24—H24A 0.980 C44—H44A 0.980
C24—H24B 0.980 C44—H44B 0.980
C24—H24C 0.980 C44—H44C 0.980
C25—C26 1.520 (2) C45—C46 1.518 (3)
C25—H25A 0.990 C45—H45A 0.990
C26—H26A 0.980 C46—H46A 0.980
C26—H26B 0.980 C46—H46B 0.980
C26—H26C 0.980 C46—H46C 0.980
C1—O1—H1 108.7 (13) C3—O3—H3 109.1 (12)
O1—C1—C11 104.77 (11) O3—C3—C33 105.04 (10)
O1—C1—C15 108.55 (12) O3—C3—C31 108.10 (11)
C11—C1—C15 112.51 (13) C33—C3—C31 112.32 (12)
O1—C1—C13 109.24 (12) O3—C3—C35 109.22 (11)
C11—C1—C13 112.74 (12) C33—C3—C35 112.66 (12)
C15—C1—C13 108.86 (13) C31—C3—C35 109.31 (11)
C12—C11—C1 114.86 (13) C32—C31—C3 115.09 (12)
C12—C11—H11A 108.6 C32—C31—H31A 108.5
C1—C11—H11A 108.6 C3—C31—H31A 108.5
C12—C11—H11B 108.6 C32—C31—H31B 108.5
C1—C11—H11B 108.6 C3—C31—H31B 108.5
H11A—C11—H11B 107.5 H31A—C31—H31B 107.5
C11—C12—H12A 109.5 C31—C32—H32A 109.5
C11—C12—H12B 109.5 C31—C32—H32B 109.5
H12A—C12—H12B 109.5 H32A—C32—H32B 109.5
C11—C12—H12C 109.5 C31—C32—H32C 109.5
H12A—C12—H12C 109.5 H32A—C32—H32C 109.5
H12B—C12—H12C 109.5 H32B—C32—H32C 109.5
C14—C13—C1 116.52 (13) C34—C33—C3 114.61 (12)
C14—C13—H13A 108.2 C34—C33—H33A 108.6
C1—C13—H13A 108.2 C3—C33—H33A 108.6
C14—C13—H13B 108.2 C34—C33—H33B 108.6
C1—C13—H13B 108.2 C3—C33—H33B 108.6
H13A—C13—H13B 107.3 H33A—C33—H33B 107.6
C13—C14—H14A 109.5 C33—C34—H34A 109.5
C13—C14—H14B 109.5 C33—C34—H34B 109.5
H14A—C14—H14B 109.5 H34A—C34—H34B 109.5
C13—C14—H14C 109.5 C33—C34—H34C 109.5
H14A—C14—H14C 109.5 H34A—C34—H34C 109.5
H14B—C14—H14C 109.5 H34B—C34—H34C 109.5
C16—C15—C1 115.38 (15) C36—C35—C3 115.64 (13)
C16—C15—H15A 108.4 C36—C35—H35A 108.4
C1—C15—H15A 108.4 C3—C35—H35A 108.4
C16—C15—H15B 108.4 C36—C35—H35B 108.4
C1—C15—H15B 108.4 C3—C35—H35B 108.4
H15A—C15—H15B 107.5 H35A—C35—H35B 107.4
C15—C16—H16A 109.5 C35—C36—H36A 109.5
C15—C16—H16B 109.5 C35—C36—H36B 109.5
H16A—C16—H16B 109.5 H36A—C36—H36B 109.5
C15—C16—H16C 109.5 C35—C36—H36C 109.5
H16A—C16—H16C 109.5 H36A—C36—H36C 109.5
H16B—C16—H16C 109.5 H36B—C36—H36C 109.5
supporting information
sup-7 Acta Cryst. (2006). E62, o2064–o2065
O2—C2—C21 105.01 (11) O4—C4—C45 105.39 (11)
O2—C2—C25 109.17 (11) O4—C4—C41 109.70 (11)
C21—C2—C25 112.82 (12) C45—C4—C41 111.04 (12)
O2—C2—C23 108.01 (11) O4—C4—C43 107.13 (12)
C21—C2—C23 112.38 (12) C45—C4—C43 110.84 (12)
C25—C2—C23 109.24 (11) C41—C4—C43 112.41 (12)
C2—C21—C22 115.05 (12) C42—C41—C4 116.06 (13)
C2—C21—H21A 108.5 C42—C41—H41A 108.3
C22—C21—H21A 108.5 C4—C41—H41A 108.3
C2—C21—H21B 108.5 C42—C41—H41B 108.3
C22—C21—H21B 108.5 C4—C41—H41B 108.3
H21A—C21—H21B 107.5 H41A—C41—H41B 107.4
C21—C22—H22A 109.5 C41—C42—H42A 109.5
C21—C22—H22B 109.5 C41—C42—H42B 109.5
H22A—C22—H22B 109.5 H42A—C42—H42B 109.5
C21—C22—H22C 109.5 C41—C42—H42C 109.5
H22A—C22—H22C 109.5 H42A—C42—H42C 109.5
H22B—C22—H22C 109.5 H42B—C42—H42C 109.5
C24—C23—C2 115.67 (13) C4—C43—C44 115.36 (13)
C24—C23—H23A 108.4 C4—C43—H43A 108.4
C2—C23—H23A 108.4 C44—C43—H43A 108.4
C24—C23—H23B 108.4 C4—C43—H43B 108.4
C2—C23—H23B 108.4 C44—C43—H43B 108.4
H23A—C23—H23B 107.4 H43A—C43—H43B 107.5
C23—C24—H24A 109.5 C43—C44—H44A 109.5
C23—C24—H24B 109.5 C43—C44—H44B 109.5
H24A—C24—H24B 109.5 H44A—C44—H44B 109.5
C23—C24—H24C 109.5 C43—C44—H44C 109.5
H24A—C24—H24C 109.5 H44A—C44—H44C 109.5
H24B—C24—H24C 109.5 H44B—C44—H44C 109.5
C26—C25—C2 114.90 (13) C46—C45—C4 115.63 (14)
C26—C25—H25A 108.5 C46—C45—H45A 108.4
C2—C25—H25A 108.5 C4—C45—H45A 108.4
C26—C25—H25B 108.5 C46—C45—H45B 108.4
C2—C25—H25B 108.5 C4—C45—H45B 108.4
H25A—C25—H25B 107.5 H45A—C45—H45B 107.4
C25—C26—H26A 109.5 C45—C46—H46A 109.5
C25—C26—H26B 109.5 C45—C46—H46B 109.5
H26A—C26—H26B 109.5 H46A—C46—H46B 109.5
C25—C26—H26C 109.5 C45—C46—H46C 109.5
H26A—C26—H26C 109.5 H46A—C46—H46C 109.5
H26B—C26—H26C 109.5 H46B—C46—H46C 109.5
O1—C1—C11—C12 179.62 (12) O3—C3—C31—C32 60.06 (16)
C15—C1—C11—C12 −62.65 (18) C33—C3—C31—C32 −55.35 (16)
C13—C1—C11—C12 60.93 (17) C35—C3—C31—C32 178.84 (13)
O1—C1—C13—C14 −62.97 (17) O3—C3—C33—C34 −178.48 (12)
C15—C1—C13—C14 178.65 (14) C35—C3—C33—C34 62.74 (17)
O1—C1—C15—C16 59.15 (17) O3—C3—C35—C36 −62.85 (17)
C11—C1—C15—C16 −56.33 (18) C33—C3—C35—C36 53.46 (17)
C13—C1—C15—C16 177.96 (13) C31—C3—C35—C36 179.07 (13)
O2—C2—C21—C22 −178.14 (12) O4—C4—C41—C42 72.21 (16)
C25—C2—C21—C22 −59.35 (17) C45—C4—C41—C42 −171.70 (12)
C23—C2—C21—C22 64.69 (17) C43—C4—C41—C42 −46.88 (16)
O2—C2—C23—C24 −59.26 (16) O4—C4—C43—C44 −179.22 (14)
C21—C2—C23—C24 56.11 (17) C45—C4—C43—C44 66.29 (18)
C25—C2—C23—C24 −177.89 (13) C41—C4—C43—C44 −58.64 (18)
O2—C2—C25—C26 58.77 (16) O4—C4—C45—C46 62.17 (17)
C21—C2—C25—C26 −57.57 (17) C41—C4—C45—C46 −56.55 (18)
C23—C2—C25—C26 176.67 (13) C43—C4—C45—C46 177.75 (14)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O1—H1···O4 0.84 (2) 1.98 (2) 2.7977 (16) 167.7 (18)
O2—H2···O1 0.86 (2) 1.93 (2) 2.7686 (14) 165.8 (17)
O3—H3···O2 0.87 (2) 1.92 (2) 2.7759 (15) 169.4 (18)
