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The structure of the title compound, C13H24O, (I), shows a sofa conformation of the ring with two pseudo-axial substituents. The dihedral angle between these substituents is 131.56 (12)°. Calculations using the B3LYP/6-31G* level of theory show two minima, one corresponding to the crystal structure and the other to a boat conformation of the ring with two equatorial substituents. The energy of this latter conformation is 17.4 kcal mol-1 higher than that of (I). The mol­ecule forms an infinite co-operative hydrogen-bonded chain running in the b direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107065468/sk3183sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107065468/sk3183Isup2.hkl
Contains datablock I

CCDC reference: 681552

Comment top

Strained molecules have been known for about a century, but interest in these species is still relevant today. For six-membered ring molecules having strong interactions between a tert-butyl group and a vicinal substituent, the gauche interaction provides sufficient steric strain to produce unique conformational (Aycard & Bodot, 1975; Stolow, Groom & Lewis, 1969; Stolow, Gallo & Marini, 1969; Viani & Lapasset, 1981) and particular reaction stereoselectivities (Aycard & Bodot, 1973; Pizzala et al., 1978; Bouteiller-Prati et al., 1981). Thus, we have shown that cis-2-tert-butylcyanocyclohexane is more stable than its trans isomer by 1.5 kcal mol-1 (Aycard & Bodot, 1973) (1 kcal mol-1 = 4.184 kJ mol-1). For cyclohexanones (Lafrance et al., 1976; Viani et al., 1978) and trans-3-tert-butyl-4-X-cyclohexenes in solution, large conformational heterogeneities have been detected and the existence of pseudo-axial tert-butyl has been postulated (Aycard & Bodot, 1975; Lafrance et al., 1977; Bouteiller-Prati et al., 1976). X-ray analysis of a series of congested 3-tert-butyl-4-X-cyclohexene derivatives (X = CN or CO2CH3) has shown that trans stereoisomers exhibit a sofa conformation which is expected to be only 0.8 kcal mol-1 higher than for the half-chair (Bucourt, 1974) with a pseudo-equatorial tert-butyl group (Viani et al., 1978; Viani & Lapasset, 1981; Cossu et al., 1981). For the cis isomer, we have observed a half-chair conformation with a pseudo-equatorial tert-butyl group (Viani et al., 1981, 1985; Viani & Lapasset, 1981). We have never obtained a conformation with a pseudo-axial tert-butyl group.

In solution, the title compound, (I), which is similar to a 3,4-di-tert-butyl derivative, presents in its 1H NMR spectrum a very small trans 3JHH coupling constant value of 5.8 Hz between H atoms bonded to C atoms 4 and 5 (Bouteiller-Prati et al., 1976). This low value is indicative of a conformational heterogeneity with a majority of a pseudo axial tert-butyl conformer (>60%). To obtain structural data on this possible species, we carried out B3LYP calculations (GAUSSIAN03; Frisch et al., 2004) and X-ray analysis on a crystal obtained from the NMR solution of trans-3,6,6-trideuterio-3-tert-butyl 4-dimethylcarbinol cyclohexene, (I). The best way to describe the ring conformation is to use the endocyclic torsion angles Φij (central bond ij). The values obtained from our X-ray data are reported in Table 3, and are compared with the classic half-chair and sofa values (Bucourt, 1974) and with those obtained from B3LYP calculations for the two expected possible conformers, (I) and (I').

We can see that the absolute value of the torsion angle Φ23 [-6.6 (2)°] is smaller than the half-chair. In fact, the ring has a quasi-pure sofa conformation with a minor twisting of the double bond [-2.8 (3)°], as observed in other trans stereoisomers of 3-tert-butyl-4-X-cyclohexene derivatives (Viani et al., 1978, 1981). Atoms C1–C4 and C6 are coplanar to within 0.06 Å. There is also good agreement between the experimental and calculated values for all the torsion angles (ΔΦmax 2°). The value of the C1—C2—C3—C7 dihedral angle is a measure of the inclination of the C3—C7 bond with respect to the double-bond plane. The value obtained for (I) [-125.36 (19)°] is similar to that determined for trans-1-acetoxy 3-tert-butyl-4-cyanocyclohexene [-125.1 (3)°; Refererence?] and is indicative of a quasi-axial position of the tert-butyl substituent. The dihedral difference (Φ34 - Φ45) is a measure of the puckering of the ring in the C4 region (Viani et al., 1981).

A low value with respect to the half-chair value (109°) is indicative of an axial position and a large value of an axial position [Should one of these `axial' be `equatorial'?] (Chiang & Bauer, 1969; Scharpen et al., 1968). The value obtained for (I) (87°) shows that the dimethylcarbinol group adopts an isoclinal position as the tert-butyl. The C7—C3—C4—C11 torsion angle between the two substituents is 131.56 (12)° (130° theoretically), larger than the values obtained in other strained 3,4-cyclohexenes [84.4 (3), 77.4 (3) and 76.4 (3)°; Viani et al., 1979]. This value is indicative of an increasing axiality of the two substituents, as shown in Fig. 1, and allows the minimization of the gauche interaction between the two large substituents.

The bond lengths and the endocyclic valence angle values show moderate fluctuations (Δl 0.03 Å and ΔΘ 4°) compared with those obtained for similar compounds (Viani et al., 1978; Viani & Lapasset, 1981) and are similar to the values obtained from theoretical calculations. The exocyclic valence angles around the tert-butyl group are very close to the mean value observed in 3-tert-butylcyclohexenes (110.7°) and tert-butylcyclohexane (113°) compounds (Viani et al., 1978, 1981; Viani & Lapasset, 1981; Lectard et al., 1976).

Non-bonded interactions are the driving force of the geometric modifications which must give the best compromise between the different non-bonded distances. Short distances are associated with repulsive non-bonded energies. The short distances here have been selected on the basis of Allinger parametrizations; some of them must be considered as very short distances and are at the origin of the strongest non-bonded interactions (Handal et al., 1977; Allinger, 1976). Some of them are caused by the C9 methyl group of the tert-butyl [interacting?] with the ring atoms C2 and C4 and with the H atom bored [bonded?] by these atoms (Table 6).

Analysis of the packing shows an O—H···O hydrogen bond that links the molecules into infinite chains running in the b-axis direction (Fig. 2 and Table 2). These intermolecular bonds stabilize the position of the hydroxyl H atom in a gauche position. The C4—C11—O1—H11 dihedral angle is -65.2 (18)°. In the optimized structure of this conformer, similar to the gas phase, the C4—C11—O1—H11 dihedral angle is 180°.

The theoretical calculations for (I) give very good accuracy between the calculated geometric parameters and those obtained from the X-ray crystal data. For this, starting from a sofa conformation, we have modelled the structure for a diequatorial conformer. We obtain another energy minimum for the structure of (I'). This structure is 17.4 kcal mol-1 less stable than (I). If the bond lengths and valence bond angles are similar for the two conformers (Tables 4 and 5), the values of the endocyclic torsion angles (Table 3) are very different and indicate a twist-boat conformation. In solution, this compound can be neglected.

Related literature top

For related literature, see: Allinger (1976); Aycard & Bodot (1973, 1975); Bouteiller-Prati, Bouteiller & Aycard (1976, 1981); Bucourt (1974); Chiang & Bauer (1969); Cossu et al. (1981); Frisch (2004); Handal et al. (1977); Lafrance et al. (1976, 1977); Lectard et al. (1976); Parr & Yang (1989); Pizzala et al. (1978); Prince (1982); Scharpen et al. (1968); Stolow, Gallo & Marini (1969); Stolow, Groom & Lewis (1969); Viani & Lapasset (1981); Viani et al. (1978, 1979, 1985); Viani, Cossu & Lapasset (1981); Watkin (1994).

Experimental top

The synthesis of the title compound has been described previously by Bouteiller-Prati et al. (1981). The compound was obtained as white needles by crystallization from a solution in chloroform. The computational method to establish the molecular structure and the relative energy of the two conformations was that of ab initio calculations carried out using GAUSSIAN03 (Frisch et al., 2004). The different systems were optimized at the B3LYP/6–31G* level of theory (Parr & Yang, 1989).

Refinement top

Weighting was based on a Chebychev polynomial (Watkin, 1994; Prince, 1982). All H atoms were discernible in a difference Fourier map. The C—H distances were constrained to 0.95 and 0.98 Å for aryl and methyl H atoms, respectively, with Uiso(H) = 1.2Ueq(C). The positional parameter of atom H11 was refined freely and Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: COLLECT (Nonius, 1997); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top
[Figure 1] Fig. 1. A view of the title molecule, with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as spheres of arbitary radii.
[Figure 2] Fig. 2. A motif of the O—H···O hydrogen bonds forming chains in the title structure.
2-(2-tert-butylcyclohex-3-enyl)propan-2-ol top
Crystal data top
C13H24OF(000) = 440
Mr = 196.33Dx = 1.042 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 15244 reflections
a = 13.0192 (4) Åθ = 1.6–30.1°
b = 6.0581 (2) ŵ = 0.06 mm1
c = 16.3514 (4) ÅT = 294 K
β = 103.915 (2)°Needle, colourless
V = 1251.81 (7) Å30.30 × 0.25 × 0.25 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
2533 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
Graphite monochromatorθmax = 30.1°, θmin = 1.6°
ϕ scansh = 1818
15244 measured reflectionsk = 88
3625 independent reflectionsl = 2222
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 0.91 Method, part 1, Chebychev polynomial (Watkin, 1994, Prince, 1982), [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)],
where Ai are the Chebychev coefficients listed below and x = F /Fmax. Method = Robust Weighting (Prince, 1982), W = [weight] * [1-(δF/6*σF)2]2 Ai are: 430, 475, 362, 83.5.
2533 reflections(Δ/σ)max = 0.000254
130 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.17 e Å3
93 constraints
Crystal data top
C13H24OV = 1251.81 (7) Å3
Mr = 196.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.0192 (4) ŵ = 0.06 mm1
b = 6.0581 (2) ÅT = 294 K
c = 16.3514 (4) Å0.30 × 0.25 × 0.25 mm
β = 103.915 (2)°
Data collection top
Nonius KappaCCD
diffractometer
2533 reflections with I > 2σ(I)
15244 measured reflectionsRint = 0.040
3625 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 0.91Δρmax = 0.19 e Å3
2533 reflectionsΔρmin = 0.17 e Å3
130 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. The reflections 1 1 0; 0 1 1 have been measured with too low intensities. It might be caused by some systematical error, probably by shielding by a beam stop of this diffraction. There were not used in the refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.60835 (13)0.1174 (3)0.27863 (12)0.0627
C20.64613 (13)0.1492 (3)0.21159 (11)0.0539
C30.73873 (10)0.0307 (2)0.19137 (8)0.0399
C40.79559 (10)0.1201 (2)0.26492 (8)0.0357
C50.71811 (12)0.2177 (3)0.31305 (9)0.0467
C60.64943 (13)0.0505 (3)0.34399 (11)0.0595
C70.70934 (12)0.0792 (3)0.10229 (9)0.0480
C80.80774 (16)0.1728 (5)0.08026 (11)0.0861
C90.66458 (19)0.0944 (4)0.03570 (11)0.0811
C100.62814 (17)0.2615 (4)0.09684 (12)0.0757
C110.89546 (10)0.0086 (3)0.32095 (8)0.0402
C120.87721 (14)0.2158 (3)0.35544 (12)0.0586
C130.95169 (13)0.1590 (3)0.39207 (9)0.0546
O10.96826 (9)0.0342 (2)0.26814 (7)0.0558
H10.55240.20560.28510.0756*
H20.61240.25480.17310.0656*
H30.78990.14670.18770.0487*
H40.82180.24620.23840.0436*
H510.75910.29660.36160.0566*
H520.67190.32030.27590.0566*
H610.69120.02250.39380.0743*
H620.59040.12650.35810.0743*
H810.83880.28340.12080.1040*
H820.85770.05590.08110.1040*
H830.78900.23750.02510.1040*
H910.64660.02630.01890.0950*
H920.71650.20750.03660.0950*
H930.60230.15870.04750.0950*
H1010.65560.37180.13850.0912*
H1020.61350.32710.04180.0912*
H1030.56410.20120.10690.0912*
H110.9871 (18)0.086 (4)0.2534 (15)0.0840*
H1210.94290.27160.38900.0716*
H1220.82710.20250.38970.0716*
H1230.85020.31550.30970.0716*
H1311.01290.08510.42530.0646*
H1320.97320.29190.36890.0646*
H1330.90440.19520.42700.0646*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0498 (9)0.0728 (12)0.0709 (11)0.0143 (9)0.0251 (8)0.0069 (10)
C20.0509 (8)0.0517 (9)0.0603 (9)0.0152 (7)0.0156 (7)0.0057 (8)
C30.0369 (6)0.0430 (7)0.0409 (7)0.0005 (6)0.0119 (5)0.0035 (6)
C40.0362 (6)0.0376 (7)0.0351 (6)0.0001 (5)0.0118 (5)0.0018 (5)
C50.0471 (8)0.0504 (8)0.0442 (7)0.0093 (7)0.0138 (6)0.0041 (7)
C60.0486 (9)0.0820 (13)0.0546 (9)0.0069 (9)0.0260 (7)0.0022 (9)
C70.0422 (7)0.0640 (10)0.0372 (7)0.0034 (7)0.0083 (6)0.0020 (7)
C80.0647 (11)0.149 (2)0.0447 (9)0.0267 (13)0.0142 (8)0.0209 (12)
C90.0946 (15)0.0952 (17)0.0473 (9)0.0064 (13)0.0048 (9)0.0167 (10)
C100.0873 (14)0.0804 (14)0.0560 (10)0.0232 (12)0.0104 (9)0.0137 (10)
C110.0372 (6)0.0478 (8)0.0381 (6)0.0034 (6)0.0139 (5)0.0028 (6)
C120.0547 (9)0.0522 (9)0.0692 (11)0.0099 (8)0.0160 (8)0.0167 (8)
C130.0507 (8)0.0657 (11)0.0430 (8)0.0016 (8)0.0030 (6)0.0004 (8)
O10.0414 (6)0.0790 (9)0.0515 (6)0.0096 (6)0.0200 (5)0.0016 (6)
Geometric parameters (Å, º) top
C1—C21.319 (2)C8—H810.960
C1—H10.930C8—H820.960
C2—C31.506 (2)C8—H830.960
C2—H20.930C9—H910.960
C3—C41.5493 (18)C9—H920.960
C3—C71.563 (2)C9—H930.960
C3—H30.980C10—H1010.960
C4—H40.980C10—H1020.960
C4—C51.5391 (17)C10—H1030.960
C4—C111.5534 (18)C11—C121.512 (2)
C5—C61.517 (2)C11—C131.520 (2)
C5—H510.970C11—O11.4507 (15)
C5—H520.970C12—H1210.960
C6—C11.479 (3)C12—H1220.960
C6—H610.970C12—H1230.960
C6—H620.970C13—H1310.960
C7—C81.521 (2)C13—H1320.960
C7—C91.525 (2)C13—H1330.960
C7—C101.517 (2)O1—H110.82 (2)
C1—C2—C3126.23 (15)C7—C8—H82109.1
C2—C3—C4111.64 (11)C7—C8—H83109.7
C2—C3—C7112.21 (12)C7—C9—H91109.5
C3—C4—C5111.96 (11)C7—C9—H92109.5
C3—C4—C11112.17 (11)C7—C9—H93109.4
C3—C7—C8110.37 (12)C7—C10—H101109.3
C3—C7—C9109.72 (14)C7—C10—H102109.6
C3—C7—C10112.08 (12)C7—C10—H103109.6
C4—C3—C7115.88 (12)C11—C4—H4105.6
C4—C5—C6115.16 (13)C11—C12—H121109.4
C4—C11—C12115.25 (12)C11—C12—H122109.4
C4—C11—C13111.81 (12)C11—C12—H123109.7
C4—C11—O1107.49 (10)C11—C13—H131109.6
C5—C4—C11115.09 (11)C11—C13—H132109.5
C5—C6—C1110.99 (13)C11—C13—H133109.4
C6—C1—C2123.94 (15)C11—O1—H11107.4 (16)
C8—C7—C9106.68 (15)C12—C11—C13110.10 (13)
C8—C7—C10109.22 (18)C12—C11—O1104.19 (12)
C9—C7—C10108.60 (15)C13—C11—O1107.40 (12)
C1—C2—H2116.9H51—C5—H52109.5
C1—C6—H61109.0H61—C6—H62109.5
C1—C6—H62109.2H81—C8—H82109.5
C2—C1—H1118.1H81—C8—H83109.5
C2—C3—H3105.3H82—C8—H83109.5
C3—C2—H2116.9H91—C9—H92109.5
C3—C4—H4105.6H91—C9—H93109.5
C4—C3—H3105.4H92—C9—H93109.5
C4—C5—H51108.0H101—C10—H102109.5
C4—C5—H52108.1H101—C10—H103109.5
C5—C4—H4105.5H102—C10—H103109.5
C5—C6—H61109.1H121—C12—H122109.5
C5—C6—H62109.0H121—C12—H123109.5
C6—C1—H1118.0H122—C12—H123109.5
C6—C5—H51108.0H131—C13—H132109.5
C6—C5—H52108.1H131—C13—H133109.5
C7—C3—H3105.4H132—C13—H133109.5
C7—C8—H81109.6
C1—C2—C3—C46.6 (2)C4—C5—C6—C142.94 (19)
C1—C2—C3—C7125.36 (19)C4—C11—O1—H1165.2 (18)
C2—C3—C4—C532.81 (16)C6—C1—C2—C32.8 (3)
C2—C1—C6—C515.2 (2)C7—C3—C4—C11131.56 (12)
C3—C4—C5—C653.09 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H11···O1i0.82 (2)2.42 (2)3.2320 (17)170 (2)
C3—H3···O10.982.472.9499 (18)110
Symmetry code: (i) x+2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC13H24O
Mr196.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)13.0192 (4), 6.0581 (2), 16.3514 (4)
β (°) 103.915 (2)
V3)1251.81 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.06
Crystal size (mm)0.30 × 0.25 × 0.25
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
15244, 3625, 2533
Rint0.040
(sin θ/λ)max1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.105, 0.91
No. of reflections2533
No. of parameters130
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.17

Computer programs: COLLECT (Nonius, 1997), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top
C1—C21.319 (2)
C1—C2—C3126.23 (15)C5—C6—C1110.99 (13)
C4—C5—C6115.16 (13)C6—C1—C2123.94 (15)
C1—C2—C3—C46.6 (2)C3—C4—C5—C653.09 (16)
C1—C2—C3—C7125.36 (19)C4—C5—C6—C142.94 (19)
C2—C3—C4—C532.81 (16)C6—C1—C2—C32.8 (3)
C2—C1—C6—C515.2 (2)C7—C3—C4—C11131.56 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H11···O1i0.82 (2)2.42 (2)3.2320 (17)170 (2)
C3—H3···O10.982.472.9499 (18)110
Symmetry code: (i) x+2, y1/2, z+1/2.
Comparison of endocyclic torsion angles (°) top
BondΦij(Ia)(Ib)(I'b)(II)(III)
C1—C2Φ12-2.8 (3)-26.20-5.7
C2—C3Φ23-6.6 (2)-7-31-160
C3—C4Φ3432.81 (16)3210.84632
C4—C5Φ45-53.09 (16)-5130-63-58
C5—C6Φ4542.94 (19)41-53.34651
C6—C1Φ61-15.2 (2)-1436.2-16-20
Data for (Ia) are from experiment, (Ib) from calculations, (I'b) from calculations, (II) for a cyclohexene half-chair and (III) for a cyclohexene sofa.
Experimental and calculated exocyclic valence bond angles (°) top
AngleExperimental value for (I)Calculated value for (I)Average valueCalculated value for (I')
C2—C3—C7112.21 (12)112.9111109.9
C3—C7—C8110.37 (12)109.9111111.6
C3—C7—C9109.72 (14)109.6111112.3
C3—C7—C10112.08 (12)112.3108108.9
C3—C4—C11112.17 (11)112.2112112.5
C4—C3—C7115.88 (12)114.7114114.6
C4—C11—C13111.81 (12)111.5111.6
C4—C11—C12115.25 (12)115.3112.3
C4—C11—O1107.409 (10)103.2105.4
C5—C4—C11115.09 (11)115.5107108.8
Average values obtained from three strained trans 3-tert-butyl 4-X-cyclohexenes (Viani et al., 1978)
Experimental and calculated endocyclic valence bond angles (°) top
AngleExperimental value for (I)Calculated value for (I)Calculated value for (I')
C1—C2—C3126.30 (15)126.1123.9
C2—C3—C4111.64 (11)112.2112.9
C3—C4—C5111.96 (11)112.3114.0
C4—C5—C6115.16 (13)115.5115.3
C5—C6—C1110.99 (13)111.5108.9
C6—C1—C2123.94 (15)123.6120.4
Intramolecular short distances (Å) between non-bonded atoms top
DistanceLengthDistanceLength
O1···H32.47H3···H922.45
C2···C92.96 (3)H3···H822.46
C2···H932.60H3···H1232.21
C2···H1032.77H4···H812.00
C3···H1232.73H4···H112.32
C4···C83.07 (3)H51···H1332.03
C4···H1012.84H52···H1012.22
C9···H22.68H61···H1222.09
C10···H522.86H83···H1012.42
C12···H32.74H92···H822.41
C13···H512.57H91···H1022.44
H2···H932.10H91···H1022.44
 

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