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Acta Cryst. (2009). E65, o1481    [ doi:10.1107/S1600536809020315 ]

tert-Butyl N-hydroxy-N-[(1S*,2R*)-2-(1-naphthyl)cyclopent-3-en-1-yl]carbamate

A. J. Lough, B. P. Machin and W. Tam

Abstract top

The relative stereochemistry of the title compound, C20H23NO3, was established by X-ray analysis. The asymmetric unit contains two independent molecules. In the crystal structure, each type of molecule forms a centrosymmetric dimer via pairs of intermolecular O-H...O hydrogen bonds, resulting in an R22(10) loop in each case.

Comment top

We have recently studied the addition of aryl groups to a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene system using a [Rh(COD)Cl]2 (COD = cyclooctadiene) catalyst. The reaction produces two stereoisomers, the absolute stereochemistry of the title major isomer,(I), was determined by single-crystal X-ray diffraction.

The asymmetric unit of (I) contains two independent molecules [A and B] which are shown in Figs 1 and 2. In the crystal structure, each type of molecule is linked into a centrosymmetric dimer via intermolecular O—H···O hydrogen bonds (Fig. 3). Each dimer forms a R22(10) graph set (Bernstein et al., 1995).

Related literature top

For hydrogen-bond graph sets, see: Bernstein et al. (1995).

Experimental top

3-aza-2-oxabicyclo[2.2.1]hept-5-ene (I) (see Fig. 4) (99.4 mg, 0.504 mmol) and 1-napthalene boronic acid (103.1 mg, 0.599 mmol) were weighed into a dry vial and purged with nitrogen. Dried MeOH (2.3 ml) was measured out into a dry vial and purged with nitrogen. Inside an inert atmosphere (Ar) dry box, [Rh(COD)Cl]2 (15.6 mg, 0.031 mmol) and (±)-BINAP (41.0 mg, 0.066 mmol) were weighed out and dissolved in methanol (1.0 ml), and stirred for 30 minutes. NaHCO3 (85.4 mg, 1.03 mmol) was added to the vial containing the bicyclic alkene and dissolved in MeOH (1.3 ml) and transferred to the vial with the catalyst. The reaction was heated to 333 K and stirred overnight. The crude product was purified using column chromatography (EtOAc:hexanes = 1:4) to give (II) as the major stereoisomer as an off white solid (58.1 mg, 0.179 mmol, 36%). Colourless blocks of (I) were grown from a solution of the title compound in dichloromethane/hexanes.

Refinement top

H atoms bonded to C atoms were placed in calculated positions with C—H = 0.95–1.00 and they were included in the refinement in a riding-model approximation with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl C atoms. H atoms bonded to O atoms were located in difference maps and refined independently with isotropic displacement parameters.

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of molecule A of (I): displacement ellipsoids are drawn at the 30% probabilty level.
[Figure 2] Fig. 2. View of molecule B of (I): displacement ellipsoids are drawn at the 30% probabilty level.
[Figure 3] Fig. 3. Part of the crystal structure with hydrogen bonds shown as dashed lines.
[Figure 4] Fig. 4. The synthetic scheme
tert-Butyl N-hydroxy-N-[(1S*,2R*)- 2-(1-naphthyl)cyclopent-3-en-1-yl]carbamate top
Crystal data top
C20H23NO3Z = 4
Mr = 325.39F(000) = 696
Triclinic, P1Dx = 1.258 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4710 (5) ÅCell parameters from 10769 reflections
b = 8.4880 (4) Åθ = 2.6–26.3°
c = 26.1836 (12) ŵ = 0.08 mm−1
α = 95.980 (3)°T = 150 K
β = 95.419 (2)°Block, colourless
γ = 111.960 (2)°0.22 × 0.18 × 0.14 mm
V = 1718.32 (15) Å3
Data collection top
Nonius KappaCCD
diffractometer		6622 independent reflections
Radiation source: fine-focus sealed tube4089 reflections with I > 2σ(I)
graphiteRint = 0.035
Detector resolution: 9 pixels mm-1θmax = 26.3°, θmin = 2.6°
φ scans and ω scans with κ offsetsh = −10→10
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)		k = −10→10
Tmin = 0.918, Tmax = 0.989l = −32→30
10769 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.167 w = 1/[σ2(Fo2) + (0.0652P)2 + 0.4209P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
6622 reflectionsΔρmax = 0.33 e Å−3
448 parametersΔρmin = −0.24 e Å−3
0 restraintsExtinction correction: SHELXTL (Version 6.1; Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0086 (16)
Crystal data top
C20H23NO3γ = 111.960 (2)°
Mr = 325.39V = 1718.32 (15) Å3
Triclinic, P1Z = 4
a = 8.4710 (5) ÅMo Kα radiation
b = 8.4880 (4) ŵ = 0.08 mm−1
c = 26.1836 (12) ÅT = 150 K
α = 95.980 (3)°0.22 × 0.18 × 0.14 mm
β = 95.419 (2)°
Data collection top
Nonius KappaCCD
diffractometer		6622 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)		4089 reflections with I > 2σ(I)
Tmin = 0.918, Tmax = 0.989Rint = 0.035
10769 measured reflectionsθmax = 26.3°
Refinement top
R[F2 > 2σ(F2)] = 0.057H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.167Δρmax = 0.33 e Å−3
S = 1.10Δρmin = −0.24 e Å−3
6622 reflectionsAbsolute structure: ?
448 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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*/Ueq
O1A0.6043 (2)0.4234 (3)0.45322 (7)0.0357 (5)
H1OA0.632 (5)0.537 (5)0.4709 (13)0.077 (12)*
O2A0.1728 (2)0.2277 (2)0.39933 (6)0.0282 (4)
O3A0.2995 (2)0.2761 (2)0.48346 (7)0.0330 (5)
N1A0.4517 (3)0.3873 (3)0.41951 (8)0.0286 (5)
C1A0.4750 (3)0.3877 (3)0.36519 (10)0.0284 (6)
H20.36030.36180.34460.034*
C2A0.5993 (4)0.5614 (4)0.35413 (11)0.0401 (7)
H30.53800.63630.34550.048*
H40.69080.62170.38400.048*
C3A0.6710 (4)0.5081 (4)0.30832 (11)0.0417 (7)
H3A0.73190.58470.28640.050*
C4A0.6395 (4)0.3422 (4)0.30201 (11)0.0396 (7)
H4A0.67350.28550.27450.047*
C5A0.5439 (3)0.2528 (3)0.34302 (10)0.0297 (6)
H50.62800.24220.37050.036*
C6A0.4023 (3)0.0765 (3)0.32410 (9)0.0286 (6)
C7A0.3103 (4)0.0433 (4)0.27530 (10)0.0326 (7)
H60.33900.13030.25370.039*
C8A0.1752 (4)−0.1155 (4)0.25649 (10)0.0363 (7)
H70.1135−0.13420.22270.044*
C9A0.1323 (4)−0.2427 (4)0.28649 (11)0.0367 (7)
H80.0412−0.35000.27330.044*
C10A0.2221 (3)−0.2172 (3)0.33715 (10)0.0306 (6)
C11A0.1782 (4)−0.3471 (4)0.36895 (11)0.0372 (7)
H11A0.0884−0.45530.35580.045*
C12A0.2619 (4)−0.3208 (4)0.41804 (12)0.0406 (7)
H12A0.2302−0.40960.43890.049*
C13A0.3959 (4)−0.1609 (4)0.43766 (11)0.0374 (7)
H13A0.4550−0.14270.47180.045*
C14A0.4416 (4)−0.0323 (3)0.40817 (10)0.0312 (6)
H14A0.53120.07500.42230.037*
C15A0.3582 (3)−0.0552 (3)0.35665 (9)0.0280 (6)
C16A0.3056 (3)0.2920 (3)0.43773 (10)0.0268 (6)
C17A−0.0021 (3)0.1253 (3)0.40984 (9)0.0295 (6)
C18A−0.1061 (4)0.0807 (4)0.35615 (10)0.0396 (7)
H18A−0.09930.18660.34290.059*
H18B−0.22640.00990.35810.059*
H18C−0.05970.01670.33270.059*
C19A−0.0044 (4)−0.0364 (3)0.42982 (11)0.0375 (7)
H19A0.0770−0.00540.46190.056*
H19B0.0289−0.10490.40370.056*
H19C−0.1204−0.10360.43670.056*
C20A−0.0614 (4)0.2358 (4)0.44690 (11)0.0369 (7)
H20A0.01470.27100.48020.055*
H20B−0.17940.16940.45240.055*
H20C−0.05760.33810.43190.055*
O1B0.4907 (3)0.6687 (2)0.05737 (8)0.0385 (5)
H1OB0.557 (5)0.667 (5)0.0335 (13)0.071 (12)*
O2B0.3481 (2)0.2662 (2)0.09741 (6)0.0301 (4)
O3B0.3099 (2)0.3398 (2)0.01728 (7)0.0352 (5)
N1B0.4828 (3)0.5352 (3)0.08597 (8)0.0306 (5)
C1B0.5343 (3)0.5915 (3)0.14138 (10)0.0296 (6)
H100.52930.48850.15760.036*
C2B0.7184 (4)0.7273 (4)0.15626 (11)0.0381 (7)
H110.80360.67350.15960.046*
H120.74830.80800.13070.046*
C3B0.7070 (4)0.8157 (3)0.20804 (11)0.0380 (7)
H3B0.80400.88560.23280.046*
C4B0.5462 (4)0.7841 (3)0.21470 (11)0.0369 (7)
H130.51380.82840.24500.044*
C5B0.4195 (3)0.6695 (3)0.16871 (10)0.0310 (6)
H140.38830.74350.14570.037*
C6B0.2554 (3)0.5356 (3)0.18060 (10)0.0276 (6)
C7B0.2584 (4)0.4624 (4)0.22474 (10)0.0351 (7)
H150.36420.49700.24720.042*
C8B0.1108 (4)0.3382 (4)0.23788 (11)0.0394 (7)
H160.11740.28980.26870.047*
C9B−0.0427 (4)0.2871 (4)0.20617 (11)0.0404 (7)
H17−0.14290.20460.21550.049*
C10B−0.0543 (4)0.3553 (3)0.15974 (11)0.0349 (7)
C11B−0.2113 (4)0.2982 (4)0.12554 (12)0.0440 (8)
H11B−0.31220.21620.13480.053*
C12B−0.2198 (4)0.3590 (4)0.07978 (12)0.0459 (8)
H12B−0.32580.31790.05710.055*
C13B−0.0730 (4)0.4820 (4)0.06591 (11)0.0422 (8)
H13B−0.08030.52540.03410.051*
C14B0.0808 (4)0.5398 (4)0.09798 (10)0.0330 (7)
H14B0.17960.62180.08770.040*
C15B0.0967 (3)0.4806 (3)0.14624 (10)0.0292 (6)
C16B0.3713 (3)0.3763 (3)0.06313 (10)0.0286 (6)
C17B0.2321 (4)0.0831 (3)0.08300 (10)0.0312 (6)
C18B0.2446 (4)0.0185 (4)0.13454 (10)0.0426 (8)
H18D0.36360.03270.14540.064*
H18E0.1692−0.10340.13070.064*
H18F0.20910.08450.16080.064*
C19B0.0503 (4)0.0681 (4)0.06712 (11)0.0376 (7)
H19D0.01300.12250.09580.056*
H19E−0.0263−0.05350.05850.056*
H19F0.04630.12550.03670.056*
C20B0.2987 (4)−0.0052 (4)0.04207 (11)0.0381 (7)
H20D0.41690.00970.05460.057*
H20E0.29690.04550.01020.057*
H20F0.2255−0.12800.03490.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0266 (11)0.0377 (12)0.0348 (11)0.0093 (9)−0.0081 (9)−0.0052 (9)
O2A0.0224 (10)0.0306 (10)0.0256 (9)0.0043 (8)0.0011 (8)0.0027 (8)
O3A0.0349 (12)0.0330 (11)0.0258 (10)0.0084 (9)0.0014 (8)0.0020 (8)
N1A0.0230 (13)0.0302 (12)0.0263 (11)0.0061 (10)−0.0029 (10)−0.0014 (9)
C1A0.0262 (15)0.0256 (14)0.0287 (14)0.0057 (12)0.0013 (12)0.0023 (11)
C2A0.0356 (18)0.0331 (16)0.0432 (17)0.0037 (14)0.0048 (14)0.0074 (13)
C3A0.0304 (17)0.0429 (19)0.0475 (18)0.0056 (15)0.0090 (14)0.0191 (15)
C4A0.0335 (17)0.051 (2)0.0355 (16)0.0153 (15)0.0111 (13)0.0087 (14)
C5A0.0280 (15)0.0317 (15)0.0286 (14)0.0103 (13)0.0044 (12)0.0049 (12)
C6A0.0297 (16)0.0320 (15)0.0264 (14)0.0150 (13)0.0065 (12)0.0003 (12)
C7A0.0386 (17)0.0340 (16)0.0282 (14)0.0178 (14)0.0053 (13)0.0031 (12)
C8A0.0387 (18)0.0415 (18)0.0286 (15)0.0192 (15)−0.0006 (13)−0.0048 (13)
C9A0.0325 (17)0.0327 (16)0.0392 (16)0.0102 (14)0.0029 (13)−0.0074 (13)
C10A0.0328 (16)0.0265 (15)0.0338 (15)0.0138 (13)0.0059 (13)0.0002 (12)
C11A0.0404 (18)0.0241 (15)0.0459 (18)0.0119 (14)0.0068 (15)0.0020 (13)
C12A0.049 (2)0.0292 (16)0.0482 (18)0.0181 (15)0.0119 (16)0.0112 (14)
C13A0.0421 (18)0.0396 (17)0.0337 (15)0.0205 (15)0.0026 (13)0.0037 (13)
C14A0.0332 (16)0.0282 (15)0.0318 (15)0.0119 (13)0.0033 (12)0.0041 (12)
C15A0.0291 (16)0.0304 (15)0.0282 (14)0.0156 (13)0.0068 (12)0.0018 (12)
C16A0.0265 (15)0.0235 (14)0.0276 (15)0.0085 (12)−0.0004 (12)0.0004 (11)
C17A0.0230 (15)0.0308 (15)0.0284 (14)0.0042 (12)0.0030 (12)0.0020 (12)
C18A0.0299 (17)0.0461 (18)0.0353 (16)0.0081 (14)0.0022 (13)0.0021 (14)
C19A0.0388 (18)0.0296 (16)0.0397 (16)0.0078 (14)0.0090 (14)0.0035 (13)
C20A0.0299 (16)0.0363 (16)0.0429 (16)0.0115 (14)0.0085 (13)0.0013 (13)
O1B0.0491 (14)0.0319 (11)0.0389 (11)0.0159 (10)0.0155 (10)0.0143 (9)
O2B0.0367 (11)0.0238 (10)0.0248 (9)0.0076 (9)−0.0009 (8)0.0031 (8)
O3B0.0370 (12)0.0413 (12)0.0261 (10)0.0137 (10)0.0046 (9)0.0057 (8)
N1B0.0369 (14)0.0251 (12)0.0304 (12)0.0104 (11)0.0089 (11)0.0098 (10)
C1B0.0288 (15)0.0280 (15)0.0300 (14)0.0089 (13)0.0053 (12)0.0023 (12)
C2B0.0279 (16)0.0349 (16)0.0458 (17)0.0061 (13)0.0072 (13)0.0028 (14)
C3B0.0324 (17)0.0270 (15)0.0453 (17)0.0044 (13)0.0003 (14)−0.0021 (13)
C4B0.0405 (19)0.0273 (15)0.0360 (16)0.0086 (14)0.0044 (14)−0.0059 (12)
C5B0.0291 (16)0.0257 (15)0.0374 (15)0.0097 (13)0.0050 (12)0.0040 (12)
C6B0.0276 (15)0.0247 (14)0.0309 (14)0.0103 (12)0.0077 (12)0.0016 (11)
C7B0.0342 (17)0.0375 (17)0.0350 (16)0.0154 (14)0.0082 (13)0.0032 (13)
C8B0.046 (2)0.0403 (17)0.0395 (16)0.0207 (16)0.0191 (15)0.0131 (14)
C9B0.0358 (18)0.0336 (17)0.0531 (19)0.0122 (14)0.0190 (16)0.0054 (14)
C10B0.0296 (17)0.0305 (15)0.0434 (17)0.0112 (13)0.0093 (14)−0.0013 (13)
C11B0.0298 (17)0.0405 (18)0.058 (2)0.0112 (15)0.0101 (15)−0.0036 (16)
C12B0.0288 (18)0.053 (2)0.054 (2)0.0198 (16)−0.0016 (15)−0.0103 (17)
C13B0.042 (2)0.0512 (19)0.0394 (17)0.0276 (17)0.0021 (15)0.0004 (15)
C14B0.0312 (16)0.0338 (16)0.0363 (16)0.0154 (13)0.0066 (13)0.0031 (13)
C15B0.0282 (16)0.0256 (14)0.0352 (15)0.0126 (13)0.0070 (12)−0.0003 (12)
C16B0.0302 (16)0.0331 (16)0.0249 (14)0.0143 (13)0.0068 (12)0.0054 (12)
C17B0.0356 (17)0.0216 (14)0.0306 (14)0.0062 (13)0.0033 (12)−0.0006 (11)
C18B0.057 (2)0.0305 (16)0.0341 (16)0.0111 (15)0.0031 (15)0.0036 (13)
C19B0.0315 (17)0.0350 (16)0.0384 (16)0.0064 (14)0.0063 (13)−0.0050 (13)
C20B0.0380 (18)0.0313 (16)0.0429 (16)0.0133 (14)0.0045 (14)−0.0019 (13)
Geometric parameters (Å, °) top
O1A—N1A1.405 (3)O1B—N1B1.407 (3)
O1A—H1OA0.96 (4)O1B—H1OB0.88 (3)
O2A—C16A1.337 (3)O2B—C16B1.337 (3)
O2A—C17A1.480 (3)O2B—C17B1.479 (3)
O3A—C16A1.223 (3)O3B—C16B1.222 (3)
N1A—C16A1.363 (3)N1B—C16B1.357 (3)
N1A—C1A1.454 (3)N1B—C1B1.450 (3)
C1A—C2A1.534 (4)C1B—C2B1.536 (4)
C1A—C5A1.554 (3)C1B—C5B1.553 (3)
C1A—H21.0000C1B—H101.0000
C2A—C3A1.497 (4)C2B—C3B1.509 (4)
C2A—H30.9900C2B—H110.9900
C2A—H40.9900C2B—H120.9900
C3A—C4A1.321 (4)C3B—C4B1.319 (4)
C3A—H3A0.9500C3B—H3B0.9500
C4A—C5A1.503 (4)C4B—C5B1.510 (4)
C4A—H4A0.9500C4B—H130.9500
C5A—C6A1.521 (4)C5B—C6B1.515 (4)
C5A—H51.0000C5B—H141.0000
C6A—C7A1.375 (4)C6B—C7B1.371 (4)
C6A—C15A1.436 (4)C6B—C15B1.431 (4)
C7A—C8A1.404 (4)C7B—C8B1.402 (4)
C7A—H60.9500C7B—H150.9500
C8A—C9A1.361 (4)C8B—C9B1.366 (4)
C8A—H70.9500C8B—H160.9500
C9A—C10A1.418 (4)C9B—C10B1.410 (4)
C9A—H80.9500C9B—H170.9500
C10A—C11A1.411 (4)C10B—C11B1.417 (4)
C10A—C15A1.427 (4)C10B—C15B1.428 (4)
C11A—C12A1.362 (4)C11B—C12B1.359 (4)
C11A—H11A0.9500C11B—H11B0.9500
C12A—C13A1.409 (4)C12B—C13B1.400 (4)
C12A—H12A0.9500C12B—H12B0.9500
C13A—C14A1.362 (4)C13B—C14B1.369 (4)
C13A—H13A0.9500C13B—H13B0.9500
C14A—C15A1.421 (4)C14B—C15B1.421 (4)
C14A—H14A0.9500C14B—H14B0.9500
C17A—C19A1.513 (4)C17B—C19B1.511 (4)
C17A—C18A1.517 (4)C17B—C20B1.514 (3)
C17A—C20A1.526 (3)C17B—C18B1.518 (4)
C18A—H18A0.9800C18B—H18D0.9800
C18A—H18B0.9800C18B—H18E0.9800
C18A—H18C0.9800C18B—H18F0.9800
C19A—H19A0.9800C19B—H19D0.9800
C19A—H19B0.9800C19B—H19E0.9800
C19A—H19C0.9800C19B—H19F0.9800
C20A—H20A0.9800C20B—H20D0.9800
C20A—H20B0.9800C20B—H20E0.9800
C20A—H20C0.9800C20B—H20F0.9800
N1A—O1A—H1OA104 (2)N1B—O1B—H1OB107 (2)
C16A—O2A—C17A120.66 (19)C16B—O2B—C17B121.51 (19)
C16A—N1A—O1A114.3 (2)C16B—N1B—O1B115.0 (2)
C16A—N1A—C1A125.8 (2)C16B—N1B—C1B125.7 (2)
O1A—N1A—C1A113.7 (2)O1B—N1B—C1B113.83 (19)
N1A—C1A—C2A113.2 (2)N1B—C1B—C2B114.0 (2)
N1A—C1A—C5A114.6 (2)N1B—C1B—C5B115.4 (2)
C2A—C1A—C5A105.8 (2)C2B—C1B—C5B105.2 (2)
N1A—C1A—H2107.7N1B—C1B—H10107.3
C2A—C1A—H2107.7C2B—C1B—H10107.3
C5A—C1A—H2107.7C5B—C1B—H10107.3
C3A—C2A—C1A101.8 (2)C3B—C2B—C1B101.4 (2)
C3A—C2A—H3111.4C3B—C2B—H11111.5
C1A—C2A—H3111.4C1B—C2B—H11111.5
C3A—C2A—H4111.4C3B—C2B—H12111.5
C1A—C2A—H4111.4C1B—C2B—H12111.5
H3—C2A—H4109.3H11—C2B—H12109.3
C4A—C3A—C2A112.1 (3)C4B—C3B—C2B111.8 (3)
C4A—C3A—H3A124.0C4B—C3B—H3B124.1
C2A—C3A—H3A124.0C2B—C3B—H3B124.1
C3A—C4A—C5A112.6 (2)C3B—C4B—C5B112.3 (2)
C3A—C4A—H4A123.7C3B—C4B—H13123.8
C5A—C4A—H4A123.7C5B—C4B—H13123.8
C4A—C5A—C6A115.7 (2)C4B—C5B—C6B116.6 (2)
C4A—C5A—C1A100.6 (2)C4B—C5B—C1B100.6 (2)
C6A—C5A—C1A113.1 (2)C6B—C5B—C1B113.5 (2)
C4A—C5A—H5109.0C4B—C5B—H14108.6
C6A—C5A—H5109.0C6B—C5B—H14108.6
C1A—C5A—H5109.0C1B—C5B—H14108.6
C7A—C6A—C15A118.9 (2)C7B—C6B—C15B118.8 (3)
C7A—C6A—C5A119.6 (2)C7B—C6B—C5B119.6 (2)
C15A—C6A—C5A121.5 (2)C15B—C6B—C5B121.6 (2)
C6A—C7A—C8A121.9 (3)C6B—C7B—C8B122.3 (3)
C6A—C7A—H6119.1C6B—C7B—H15118.9
C8A—C7A—H6119.1C8B—C7B—H15118.9
C9A—C8A—C7A120.2 (3)C9B—C8B—C7B119.8 (3)
C9A—C8A—H7119.9C9B—C8B—H16120.1
C7A—C8A—H7119.9C7B—C8B—H16120.1
C8A—C9A—C10A120.8 (3)C8B—C9B—C10B120.9 (3)
C8A—C9A—H8119.6C8B—C9B—H17119.5
C10A—C9A—H8119.6C10B—C9B—H17119.5
C11A—C10A—C9A121.6 (3)C9B—C10B—C11B121.4 (3)
C11A—C10A—C15A119.3 (2)C9B—C10B—C15B119.2 (3)
C9A—C10A—C15A119.1 (2)C11B—C10B—C15B119.4 (3)
C12A—C11A—C10A121.4 (3)C12B—C11B—C10B121.0 (3)
C12A—C11A—H11A119.3C12B—C11B—H11B119.5
C10A—C11A—H11A119.3C10B—C11B—H11B119.5
C11A—C12A—C13A119.6 (3)C11B—C12B—C13B120.3 (3)
C11A—C12A—H12A120.2C11B—C12B—H12B119.8
C13A—C12A—H12A120.2C13B—C12B—H12B119.8
C14A—C13A—C12A120.7 (3)C14B—C13B—C12B120.2 (3)
C14A—C13A—H13A119.7C14B—C13B—H13B119.9
C12A—C13A—H13A119.7C12B—C13B—H13B119.9
C13A—C14A—C15A121.4 (3)C13B—C14B—C15B121.8 (3)
C13A—C14A—H14A119.3C13B—C14B—H14B119.1
C15A—C14A—H14A119.3C15B—C14B—H14B119.1
C14A—C15A—C10A117.6 (2)C14B—C15B—C10B117.2 (3)
C14A—C15A—C6A123.3 (2)C14B—C15B—C6B123.6 (3)
C10A—C15A—C6A119.1 (2)C10B—C15B—C6B119.1 (2)
O3A—C16A—O2A126.1 (2)O3B—C16B—O2B125.9 (2)
O3A—C16A—N1A123.3 (2)O3B—C16B—N1B124.1 (2)
O2A—C16A—N1A110.4 (2)O2B—C16B—N1B109.9 (2)
O2A—C17A—C19A109.8 (2)O2B—C17B—C19B109.9 (2)
O2A—C17A—C18A101.86 (19)O2B—C17B—C20B110.5 (2)
C19A—C17A—C18A110.2 (2)C19B—C17B—C20B113.5 (2)
O2A—C17A—C20A109.7 (2)O2B—C17B—C18B100.9 (2)
C19A—C17A—C20A113.1 (2)C19B—C17B—C18B109.6 (2)
C18A—C17A—C20A111.5 (2)C20B—C17B—C18B111.6 (2)
C17A—C18A—H18A109.5C17B—C18B—H18D109.5
C17A—C18A—H18B109.5C17B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C17A—C18A—H18C109.5C17B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C17A—C19A—H19A109.5C17B—C19B—H19D109.5
C17A—C19A—H19B109.5C17B—C19B—H19E109.5
H19A—C19A—H19B109.5H19D—C19B—H19E109.5
C17A—C19A—H19C109.5C17B—C19B—H19F109.5
H19A—C19A—H19C109.5H19D—C19B—H19F109.5
H19B—C19A—H19C109.5H19E—C19B—H19F109.5
C17A—C20A—H20A109.5C17B—C20B—H20D109.5
C17A—C20A—H20B109.5C17B—C20B—H20E109.5
H20A—C20A—H20B109.5H20D—C20B—H20E109.5
C17A—C20A—H20C109.5C17B—C20B—H20F109.5
H20A—C20A—H20C109.5H20D—C20B—H20F109.5
H20B—C20A—H20C109.5H20E—C20B—H20F109.5
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1A—H1OA···O3Ai0.96 (4)1.75 (4)2.689 (3)165 (3)
O1B—H1OB···O3Bii0.88 (3)1.84 (4)2.714 (3)179 (4)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1A—H1OA···O3Ai0.96 (4)1.75 (4)2.689 (3)165 (3)
O1B—H1OB···O3Bii0.88 (3)1.84 (4)2.714 (3)179 (4)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z.
Acknowledgements top

The authors wish to acknowledge NSERC Canada and the University of Toronto for funding.

references
References top

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