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COMMUNICATIONS
ISSN: 2056-9890

cis-2-(4-Meth­­oxy­phen­yl)-4-methyl-1,2-di­hydro­naphthalen-1-ol

aDepartment of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada, and bDepartment of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada
*Correspondence e-mail: alough@chem.utoronto.ca

(Received 19 March 2014; accepted 7 April 2014; online 12 April 2014)

The stereochemistry and regiochemistry of the title compound, C18H18O2, were determined by the X-ray analysis. There are two independent mol­ecules in the asymmetric unit in which the dihedral angles between the benzene rings are 88.31 (4) and 86.27 (4)°. The cyclo­hexene rings are in half-chair conformations. In the crystal, O—H⋯O hydrogen bonds link alternating types of mol­ecules into chains along [010] with graph-set C22(4).

Related literature

For metal-catalysed ring-opening reactions of oxanorbornadiene compounds, see: Jack et al. (2013[Jack, K., Fatila, E., Hillis, C. & Tam, W. (2013). Synth. Commun. 43, 1181-1187.]). For hydrogen-bond graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18O2

  • Mr = 266.32

  • Orthorhombic, P b c a

  • a = 11.4550 (3) Å

  • b = 11.2239 (3) Å

  • c = 44.3776 (10) Å

  • V = 5705.6 (2) Å3

  • Z = 16

  • Cu Kα radiation

  • μ = 0.63 mm−1

  • T = 150 K

  • 0.20 × 0.20 × 0.19 mm

Data collection
  • Bruker Kappa APEX DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.707, Tmax = 0.753

  • 34754 measured reflections

  • 4946 independent reflections

  • 4644 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.099

  • S = 1.05

  • 4946 reflections

  • 373 parameters

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

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1A—H1O⋯O1B 0.89 (2) 2.23 (2) 3.0346 (15) 150.6 (19)
O1B—H2O⋯O1Ai 0.88 (2) 2.04 (2) 2.8973 (15) 163 (2)
Symmetry code: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

We have recently investigated the metal-catalyzed ring-opening reactions of oxanorbornadiene compounds (Jack et al., 2013). When expanding this reaction using a palladium catalyst, C1-methyl substituted oxanorbornadiene (I) (see Fig. 1) reacts with 4-methoxy-1-iodobenzene (II) in the presence of PdCl2(PPh3)2, Zn, ZnCl2, Et3N in DMF, to give the ring-opening product (III) as a single regio- and stereoisomer. The stereochemistry and regiochemistry of the product was determined by this single-crystal X-ray analysis. Although different regio- and stereoisomers could be formed, the only ring-opening product obtained was found to have a cis stereochemistry.

There are two independent molecules [A and B] in the asymmetric unit which are shown in Fig. 2. The dihedral angles between the two benzene rings [C2–C7/C11–C16] are 88.31 (4) and 86.27 (4)°, for moleclues A and B respetively. The cyclohexene rings [C1/C2/C7—C10] are in half-chair conformations. In the crystal, O—H···O hydrogen bonds link alternating types of molecules into chains along [010] with graph-set C22(4) (Bernstein et al., 1995) (see Fig. 3).

Related literature top

For metal-catalysed ring-opening reactions of oxanorbornadiene compounds, see: Jack et al. (2013). For hydrogen-bond graph-set notation, see: Bernstein et al. (1995).

Experimental top

C1 methyl substituted oxanorbornadiene (I) (0.50 mmol) and 4-methoxy-1-iodobenzene (II) (0.55 mmol) were added into an oven-dried vial containing PdCl2(PPh3)2 (0.05 mmol), Zn powder (5 mmol), ZnCl2 (0.025 mmol), Et3N (4 mmol) in DMF (3 ml). The vial was sealed with a screw cap and was heated at 338 K with stirring for 16 h. The crude product was purified by column chromatography (EtOAc: hexanes = 1:4) followed by recrystallization in EtOAc:hexanes = 1:1 to give the cis ring-opening (III) in 85% yield. X-ray quality crystals were grown from a solution of the title compound in EtOAc:hexanes = 1:1.

Refinement top

Hydrogen atoms bonded to C atoms were placed in calculated positions with C—H distances ranging from 0.95–1.00 Å and included in the refinement in a riding-model approximation with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl). H atoms bonded to O atoms were refined independently with isotropic displacement parameters.

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The reaction scheme.
[Figure 2] Fig. 2. The asymmetric unit of the title compound showing 30% probability ellipsoids. The dashed line indicates a hydrogen bond.
[Figure 3] Fig. 3. Part of the crystal structure with hydrogen bonds shown as dashed lines.
cis-2-(4-Methoxyphenyl)-4-methyl-1,2-dihydronaphthalen-1-ol top
Crystal data top
C18H18O2F(000) = 2272
Mr = 266.32Dx = 1.240 Mg m3
Orthorhombic, PbcaCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2abCell parameters from 9819 reflections
a = 11.4550 (3) Åθ = 4.3–66.5°
b = 11.2239 (3) ŵ = 0.63 mm1
c = 44.3776 (10) ÅT = 150 K
V = 5705.6 (2) Å3Block, colourless
Z = 160.20 × 0.20 × 0.19 mm
Data collection top
Bruker Kappa APEX DUO CCD
diffractometer
4946 independent reflections
Radiation source: Bruker IµuS4644 reflections with I > 2σ(I)
Multi-layer optics monochromatorRint = 0.033
ϕ and ω scansθmax = 66.5°, θmin = 4.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1313
Tmin = 0.707, Tmax = 0.753k = 1313
34754 measured reflectionsl = 3452
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.047P)2 + 2.0379P]
where P = (Fo2 + 2Fc2)/3
4946 reflections(Δ/σ)max = 0.001
373 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C18H18O2V = 5705.6 (2) Å3
Mr = 266.32Z = 16
Orthorhombic, PbcaCu Kα radiation
a = 11.4550 (3) ŵ = 0.63 mm1
b = 11.2239 (3) ÅT = 150 K
c = 44.3776 (10) Å0.20 × 0.20 × 0.19 mm
Data collection top
Bruker Kappa APEX DUO CCD
diffractometer
4946 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
4644 reflections with I > 2σ(I)
Tmin = 0.707, Tmax = 0.753Rint = 0.033
34754 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.23 e Å3
4946 reflectionsΔρmin = 0.25 e Å3
373 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. 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
O1A0.22919 (8)0.26848 (9)0.120623 (19)0.0325 (2)
O2A0.68544 (7)0.53156 (8)0.07521 (2)0.0302 (2)
C1A0.20394 (10)0.22033 (10)0.09162 (3)0.0238 (2)
H1AA0.16250.14300.09490.029*
C2A0.12087 (10)0.30080 (10)0.07497 (3)0.0236 (2)
C3A0.04550 (10)0.37600 (11)0.09018 (3)0.0319 (3)
H3AA0.05120.38310.11150.038*
C4A0.03824 (12)0.44124 (12)0.07476 (4)0.0453 (4)
H4AA0.08990.49220.08550.054*
C5A0.04615 (13)0.43192 (14)0.04395 (4)0.0525 (4)
H5AA0.10240.47770.03330.063*
C6A0.02753 (13)0.35617 (14)0.02840 (3)0.0458 (4)
H6AA0.02070.34990.00710.055*
C7A0.11210 (11)0.28850 (12)0.04346 (3)0.0301 (3)
C8A0.18971 (12)0.20407 (13)0.02778 (3)0.0375 (3)
C9A0.28302 (12)0.16040 (12)0.04187 (3)0.0366 (3)
H9AA0.33160.10630.03120.044*
C10A0.31604 (10)0.19198 (11)0.07382 (3)0.0279 (3)
H10A0.35070.11880.08300.034*
C11A0.40984 (10)0.28772 (10)0.07467 (3)0.0248 (3)
C12A0.51443 (10)0.26726 (11)0.08995 (3)0.0270 (3)
H12A0.52420.19450.10060.032*
C13A0.60418 (10)0.34949 (11)0.09013 (3)0.0268 (3)
H13A0.67440.33310.10080.032*
C14A0.59110 (10)0.45625 (10)0.07467 (3)0.0237 (2)
C15A0.48724 (10)0.48025 (11)0.05977 (3)0.0256 (3)
H15A0.47690.55400.04960.031*
C16A0.39840 (10)0.39589 (11)0.05975 (3)0.0271 (3)
H16A0.32800.41270.04930.033*
C17A0.15995 (16)0.1685 (2)0.00402 (3)0.0680 (6)
H17A0.21820.11170.01140.102*
H17B0.15970.23940.01690.102*
H17C0.08260.13130.00440.102*
C18A0.67564 (12)0.63997 (12)0.05877 (3)0.0373 (3)
H18A0.74870.68480.06040.056*
H18B0.61140.68750.06700.056*
H18C0.66000.62220.03750.056*
O1B0.27739 (10)0.01439 (10)0.14040 (2)0.0434 (3)
O2B0.16899 (8)0.31196 (9)0.14391 (2)0.0425 (2)
C1B0.28972 (12)0.00485 (12)0.17196 (3)0.0346 (3)
H1BA0.32940.08350.17460.042*
C2B0.36914 (12)0.08848 (11)0.18513 (3)0.0341 (3)
C3B0.44909 (13)0.14936 (14)0.16753 (4)0.0484 (4)
H3BA0.44780.13930.14630.058*
C4B0.53099 (15)0.22476 (16)0.18035 (6)0.0670 (6)
H4BA0.58530.26590.16800.080*
C5B0.53336 (16)0.23978 (17)0.21103 (6)0.0697 (6)
H5BA0.59020.29030.22000.084*
C6B0.45262 (16)0.18112 (15)0.22903 (4)0.0569 (5)
H6BA0.45420.19290.25020.068*
C7B0.36911 (12)0.10518 (12)0.21653 (3)0.0382 (3)
C8B0.28066 (13)0.04384 (15)0.23491 (3)0.0445 (4)
C9B0.19059 (14)0.00945 (15)0.22167 (3)0.0457 (4)
H9BA0.13470.04770.23420.055*
C10B0.17150 (12)0.01309 (12)0.18803 (3)0.0362 (3)
H10B0.13850.09340.18320.043*
C11B0.08270 (11)0.07827 (12)0.17737 (3)0.0306 (3)
C12B0.01297 (12)0.05211 (12)0.15228 (3)0.0347 (3)
H12B0.02240.02210.14230.042*
C13B0.06856 (12)0.13136 (12)0.14185 (3)0.0344 (3)
H13B0.11440.11180.12470.041*
C14B0.08461 (10)0.24027 (12)0.15619 (3)0.0317 (3)
C15B0.01645 (11)0.26885 (12)0.18096 (3)0.0325 (3)
H15B0.02640.34310.19090.039*
C16B0.06686 (11)0.18773 (12)0.19112 (3)0.0314 (3)
H16B0.11410.20820.20790.038*
C17B0.29053 (18)0.0501 (2)0.26884 (4)0.0735 (6)
H17D0.22710.00400.27800.110*
H17E0.28510.13330.27540.110*
H17F0.36580.01690.27520.110*
C18B0.18281 (18)0.42644 (19)0.15585 (5)0.0792 (7)
H18D0.24330.46900.14450.119*
H18E0.10890.46990.15430.119*
H18F0.20590.42070.17710.119*
H1O0.241 (2)0.207 (2)0.1329 (5)0.077 (7)*
H2O0.266 (2)0.055 (2)0.1314 (5)0.079 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0338 (5)0.0414 (5)0.0223 (4)0.0019 (4)0.0033 (4)0.0013 (4)
O2A0.0198 (4)0.0288 (5)0.0419 (5)0.0024 (3)0.0011 (3)0.0038 (4)
C1A0.0234 (6)0.0240 (6)0.0240 (6)0.0021 (5)0.0002 (4)0.0002 (5)
C2A0.0202 (5)0.0229 (6)0.0277 (6)0.0057 (5)0.0013 (4)0.0005 (5)
C3A0.0221 (6)0.0278 (6)0.0458 (7)0.0033 (5)0.0023 (5)0.0082 (6)
C4A0.0243 (7)0.0265 (7)0.0851 (12)0.0006 (5)0.0112 (7)0.0047 (7)
C5A0.0326 (7)0.0362 (8)0.0887 (13)0.0068 (6)0.0261 (8)0.0224 (8)
C6A0.0402 (8)0.0541 (9)0.0432 (8)0.0220 (7)0.0191 (6)0.0214 (7)
C7A0.0275 (6)0.0350 (7)0.0278 (6)0.0148 (5)0.0039 (5)0.0052 (5)
C8A0.0348 (7)0.0507 (8)0.0270 (6)0.0223 (6)0.0088 (5)0.0091 (6)
C9A0.0335 (7)0.0334 (7)0.0430 (7)0.0125 (6)0.0161 (6)0.0170 (6)
C10A0.0240 (6)0.0208 (6)0.0390 (7)0.0008 (5)0.0038 (5)0.0009 (5)
C11A0.0215 (6)0.0239 (6)0.0289 (6)0.0020 (5)0.0038 (4)0.0036 (5)
C12A0.0275 (6)0.0249 (6)0.0287 (6)0.0051 (5)0.0012 (5)0.0008 (5)
C13A0.0220 (6)0.0303 (6)0.0280 (6)0.0052 (5)0.0031 (5)0.0042 (5)
C14A0.0184 (5)0.0260 (6)0.0268 (6)0.0004 (4)0.0031 (4)0.0075 (5)
C15A0.0221 (6)0.0227 (6)0.0321 (6)0.0026 (5)0.0002 (5)0.0001 (5)
C16A0.0190 (5)0.0274 (6)0.0350 (6)0.0023 (5)0.0026 (5)0.0006 (5)
C17A0.0593 (10)0.1120 (16)0.0326 (8)0.0406 (11)0.0099 (7)0.0248 (9)
C18A0.0305 (7)0.0323 (7)0.0492 (8)0.0085 (5)0.0003 (6)0.0011 (6)
O1B0.0589 (7)0.0453 (6)0.0261 (5)0.0162 (5)0.0019 (4)0.0020 (4)
O2B0.0304 (5)0.0483 (6)0.0487 (6)0.0054 (4)0.0065 (4)0.0057 (5)
C1B0.0446 (8)0.0313 (7)0.0281 (6)0.0090 (6)0.0011 (6)0.0035 (5)
C2B0.0326 (7)0.0308 (7)0.0389 (7)0.0092 (5)0.0014 (5)0.0077 (6)
C3B0.0366 (8)0.0499 (9)0.0588 (9)0.0091 (7)0.0044 (7)0.0215 (7)
C4B0.0375 (9)0.0526 (10)0.1108 (17)0.0023 (8)0.0066 (10)0.0348 (11)
C5B0.0470 (10)0.0444 (10)0.1175 (18)0.0057 (8)0.0304 (11)0.0114 (11)
C6B0.0571 (10)0.0474 (9)0.0662 (11)0.0103 (8)0.0288 (9)0.0056 (8)
C7B0.0391 (7)0.0367 (7)0.0387 (7)0.0095 (6)0.0099 (6)0.0029 (6)
C8B0.0475 (9)0.0569 (9)0.0290 (7)0.0110 (7)0.0045 (6)0.0084 (6)
C9B0.0472 (8)0.0562 (9)0.0338 (7)0.0015 (7)0.0033 (6)0.0201 (7)
C10B0.0424 (8)0.0319 (7)0.0344 (7)0.0059 (6)0.0031 (6)0.0070 (5)
C11B0.0312 (6)0.0344 (7)0.0262 (6)0.0083 (5)0.0017 (5)0.0045 (5)
C12B0.0392 (7)0.0321 (7)0.0328 (7)0.0080 (6)0.0024 (5)0.0022 (5)
C13B0.0327 (7)0.0401 (7)0.0304 (6)0.0090 (6)0.0049 (5)0.0018 (6)
C14B0.0225 (6)0.0420 (7)0.0306 (6)0.0049 (5)0.0022 (5)0.0015 (5)
C15B0.0289 (6)0.0392 (7)0.0294 (6)0.0041 (5)0.0050 (5)0.0061 (5)
C16B0.0298 (6)0.0426 (7)0.0219 (6)0.0080 (6)0.0009 (5)0.0017 (5)
C17B0.0721 (12)0.1183 (18)0.0302 (8)0.0216 (12)0.0096 (8)0.0101 (10)
C18B0.0637 (12)0.0739 (13)0.1000 (16)0.0367 (11)0.0359 (11)0.0413 (12)
Geometric parameters (Å, º) top
O1A—C1A1.4256 (14)O1B—C1B1.4239 (16)
O1A—H1O0.89 (2)O1B—H2O0.88 (2)
O2A—C14A1.3722 (14)O2B—C14B1.3705 (16)
O2A—C18A1.4231 (16)O2B—C18B1.399 (2)
C1A—C2A1.5059 (16)C1B—C2B1.506 (2)
C1A—C10A1.5408 (16)C1B—C10B1.5333 (19)
C1A—H1AA1.0000C1B—H1BA1.0000
C2A—C3A1.3834 (17)C2B—C3B1.384 (2)
C2A—C7A1.4087 (17)C2B—C7B1.406 (2)
C3A—C4A1.387 (2)C3B—C4B1.386 (3)
C3A—H3AA0.9500C3B—H3BA0.9500
C4A—C5A1.374 (3)C4B—C5B1.372 (3)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.383 (3)C5B—C6B1.388 (3)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—C7A1.401 (2)C6B—C7B1.396 (2)
C6A—H6AA0.9500C6B—H6BA0.9500
C7A—C8A1.474 (2)C7B—C8B1.472 (2)
C8A—C9A1.332 (2)C8B—C9B1.329 (2)
C8A—C17A1.5060 (19)C8B—C17B1.512 (2)
C9A—C10A1.5095 (19)C9B—C10B1.5095 (19)
C9A—H9AA0.9500C9B—H9BA0.9500
C10A—C11A1.5201 (16)C10B—C11B1.5197 (19)
C10A—H10A1.0000C10B—H10B1.0000
C11A—C16A1.3891 (17)C11B—C16B1.3837 (19)
C11A—C12A1.3956 (17)C11B—C12B1.4015 (18)
C12A—C13A1.3817 (17)C12B—C13B1.370 (2)
C12A—H12A0.9500C12B—H12B0.9500
C13A—C14A1.3889 (17)C13B—C14B1.390 (2)
C13A—H13A0.9500C13B—H13B0.9500
C14A—C15A1.3877 (16)C14B—C15B1.3862 (18)
C15A—C16A1.3900 (17)C15B—C16B1.3939 (19)
C15A—H15A0.9500C15B—H15B0.9500
C16A—H16A0.9500C16B—H16B0.9500
C17A—H17A0.9800C17B—H17D0.9800
C17A—H17B0.9800C17B—H17E0.9800
C17A—H17C0.9800C17B—H17F0.9800
C18A—H18A0.9800C18B—H18D0.9800
C18A—H18B0.9800C18B—H18E0.9800
C18A—H18C0.9800C18B—H18F0.9800
C1A—O1A—H1O107.1 (14)C1B—O1B—H2O108.9 (15)
C14A—O2A—C18A117.10 (9)C14B—O2B—C18B117.94 (12)
O1A—C1A—C2A110.12 (9)O1B—C1B—C2B109.66 (11)
O1A—C1A—C10A111.84 (9)O1B—C1B—C10B112.26 (11)
C2A—C1A—C10A113.51 (10)C2B—C1B—C10B113.26 (11)
O1A—C1A—H1AA107.0O1B—C1B—H1BA107.1
C2A—C1A—H1AA107.0C2B—C1B—H1BA107.1
C10A—C1A—H1AA107.0C10B—C1B—H1BA107.1
C3A—C2A—C7A119.99 (11)C3B—C2B—C7B119.58 (14)
C3A—C2A—C1A121.38 (11)C3B—C2B—C1B121.61 (13)
C7A—C2A—C1A118.26 (11)C7B—C2B—C1B118.52 (12)
C2A—C3A—C4A120.85 (13)C2B—C3B—C4B121.18 (17)
C2A—C3A—H3AA119.6C2B—C3B—H3BA119.4
C4A—C3A—H3AA119.6C4B—C3B—H3BA119.4
C5A—C4A—C3A119.74 (14)C5B—C4B—C3B119.73 (17)
C5A—C4A—H4AA120.1C5B—C4B—H4BA120.1
C3A—C4A—H4AA120.1C3B—C4B—H4BA120.1
C4A—C5A—C6A120.21 (13)C4B—C5B—C6B119.96 (17)
C4A—C5A—H5AA119.9C4B—C5B—H5BA120.0
C6A—C5A—H5AA119.9C6B—C5B—H5BA120.0
C5A—C6A—C7A121.17 (14)C5B—C6B—C7B121.18 (18)
C5A—C6A—H6AA119.4C5B—C6B—H6BA119.4
C7A—C6A—H6AA119.4C7B—C6B—H6BA119.4
C6A—C7A—C2A118.01 (13)C6B—C7B—C2B118.35 (15)
C6A—C7A—C8A122.73 (13)C6B—C7B—C8B122.50 (14)
C2A—C7A—C8A119.24 (11)C2B—C7B—C8B119.14 (13)
C9A—C8A—C7A119.95 (11)C9B—C8B—C7B120.00 (12)
C9A—C8A—C17A121.61 (15)C9B—C8B—C17B121.27 (16)
C7A—C8A—C17A118.44 (14)C7B—C8B—C17B118.60 (15)
C8A—C9A—C10A123.75 (12)C8B—C9B—C10B124.18 (13)
C8A—C9A—H9AA118.1C8B—C9B—H9BA117.9
C10A—C9A—H9AA118.1C10B—C9B—H9BA117.9
C9A—C10A—C11A111.50 (10)C9B—C10B—C11B112.73 (12)
C9A—C10A—C1A108.73 (10)C9B—C10B—C1B109.29 (11)
C11A—C10A—C1A115.49 (10)C11B—C10B—C1B113.94 (10)
C9A—C10A—H10A106.9C9B—C10B—H10B106.8
C11A—C10A—H10A106.9C11B—C10B—H10B106.8
C1A—C10A—H10A106.9C1B—C10B—H10B106.8
C16A—C11A—C12A117.15 (11)C16B—C11B—C12B117.49 (12)
C16A—C11A—C10A122.64 (11)C16B—C11B—C10B123.35 (11)
C12A—C11A—C10A120.17 (11)C12B—C11B—C10B119.16 (12)
C13A—C12A—C11A122.11 (11)C13B—C12B—C11B121.39 (13)
C13A—C12A—H12A118.9C13B—C12B—H12B119.3
C11A—C12A—H12A118.9C11B—C12B—H12B119.3
C12A—C13A—C14A119.55 (11)C12B—C13B—C14B120.41 (12)
C12A—C13A—H13A120.2C12B—C13B—H13B119.8
C14A—C13A—H13A120.2C14B—C13B—H13B119.8
O2A—C14A—C15A124.33 (11)O2B—C14B—C15B125.22 (12)
O2A—C14A—C13A115.97 (10)O2B—C14B—C13B115.31 (11)
C15A—C14A—C13A119.70 (11)C15B—C14B—C13B119.47 (12)
C14A—C15A—C16A119.71 (11)C14B—C15B—C16B119.41 (12)
C14A—C15A—H15A120.1C14B—C15B—H15B120.3
C16A—C15A—H15A120.1C16B—C15B—H15B120.3
C11A—C16A—C15A121.74 (11)C11B—C16B—C15B121.81 (12)
C11A—C16A—H16A119.1C11B—C16B—H16B119.1
C15A—C16A—H16A119.1C15B—C16B—H16B119.1
C8A—C17A—H17A109.5C8B—C17B—H17D109.5
C8A—C17A—H17B109.5C8B—C17B—H17E109.5
H17A—C17A—H17B109.5H17D—C17B—H17E109.5
C8A—C17A—H17C109.5C8B—C17B—H17F109.5
H17A—C17A—H17C109.5H17D—C17B—H17F109.5
H17B—C17A—H17C109.5H17E—C17B—H17F109.5
O2A—C18A—H18A109.5O2B—C18B—H18D109.5
O2A—C18A—H18B109.5O2B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
O2A—C18A—H18C109.5O2B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
O1A—C1A—C2A—C3A25.34 (14)O1B—C1B—C2B—C3B22.59 (17)
C10A—C1A—C2A—C3A151.59 (11)C10B—C1B—C2B—C3B148.85 (12)
O1A—C1A—C2A—C7A161.64 (10)O1B—C1B—C2B—C7B163.61 (11)
C10A—C1A—C2A—C7A35.38 (14)C10B—C1B—C2B—C7B37.35 (16)
C7A—C2A—C3A—C4A0.87 (18)C7B—C2B—C3B—C4B1.4 (2)
C1A—C2A—C3A—C4A173.78 (11)C1B—C2B—C3B—C4B172.34 (14)
C2A—C3A—C4A—C5A0.5 (2)C2B—C3B—C4B—C5B0.0 (2)
C3A—C4A—C5A—C6A1.2 (2)C3B—C4B—C5B—C6B1.1 (3)
C4A—C5A—C6A—C7A0.6 (2)C4B—C5B—C6B—C7B0.8 (3)
C5A—C6A—C7A—C2A0.68 (19)C5B—C6B—C7B—C2B0.5 (2)
C5A—C6A—C7A—C8A178.05 (12)C5B—C6B—C7B—C8B178.57 (15)
C3A—C2A—C7A—C6A1.42 (17)C3B—C2B—C7B—C6B1.6 (2)
C1A—C2A—C7A—C6A174.54 (11)C1B—C2B—C7B—C6B172.31 (12)
C3A—C2A—C7A—C8A177.36 (11)C3B—C2B—C7B—C8B177.51 (13)
C1A—C2A—C7A—C8A4.23 (16)C1B—C2B—C7B—C8B8.56 (18)
C6A—C7A—C8A—C9A166.49 (12)C6B—C7B—C8B—C9B167.58 (15)
C2A—C7A—C8A—C9A14.79 (18)C2B—C7B—C8B—C9B11.5 (2)
C6A—C7A—C8A—C17A14.08 (19)C6B—C7B—C8B—C17B8.4 (2)
C2A—C7A—C8A—C17A164.64 (13)C2B—C7B—C8B—C17B172.50 (15)
C7A—C8A—C9A—C10A0.12 (19)C7B—C8B—C9B—C10B0.5 (2)
C17A—C8A—C9A—C10A179.30 (13)C17B—C8B—C9B—C10B176.41 (16)
C8A—C9A—C10A—C11A98.56 (14)C8B—C9B—C10B—C11B100.29 (17)
C8A—C9A—C10A—C1A29.90 (17)C8B—C9B—C10B—C1B27.5 (2)
O1A—C1A—C10A—C9A171.04 (10)O1B—C1B—C10B—C9B169.13 (12)
C2A—C1A—C10A—C9A45.70 (13)C2B—C1B—C10B—C9B44.26 (15)
O1A—C1A—C10A—C11A44.85 (14)O1B—C1B—C10B—C11B42.02 (16)
C2A—C1A—C10A—C11A80.49 (13)C2B—C1B—C10B—C11B82.85 (14)
C9A—C10A—C11A—C16A53.71 (15)C9B—C10B—C11B—C16B31.98 (17)
C1A—C10A—C11A—C16A71.05 (15)C1B—C10B—C11B—C16B93.32 (15)
C9A—C10A—C11A—C12A123.89 (12)C9B—C10B—C11B—C12B148.38 (13)
C1A—C10A—C11A—C12A111.34 (12)C1B—C10B—C11B—C12B86.32 (15)
C16A—C11A—C12A—C13A0.81 (17)C16B—C11B—C12B—C13B0.52 (19)
C10A—C11A—C12A—C13A176.92 (11)C10B—C11B—C12B—C13B179.82 (12)
C11A—C12A—C13A—C14A0.07 (18)C11B—C12B—C13B—C14B0.4 (2)
C18A—O2A—C14A—C15A1.38 (16)C18B—O2B—C14B—C15B4.6 (2)
C18A—O2A—C14A—C13A178.12 (11)C18B—O2B—C14B—C13B175.02 (16)
C12A—C13A—C14A—O2A178.15 (10)C12B—C13B—C14B—O2B179.59 (12)
C12A—C13A—C14A—C15A1.37 (17)C12B—C13B—C14B—C15B0.76 (19)
O2A—C14A—C15A—C16A177.74 (11)O2B—C14B—C15B—C16B179.77 (11)
C13A—C14A—C15A—C16A1.75 (17)C13B—C14B—C15B—C16B0.15 (18)
C12A—C11A—C16A—C15A0.42 (17)C12B—C11B—C16B—C15B1.14 (18)
C10A—C11A—C16A—C15A177.25 (11)C10B—C11B—C16B—C15B179.21 (12)
C14A—C15A—C16A—C11A0.85 (18)C14B—C15B—C16B—C11B0.82 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1O···O1B0.89 (2)2.23 (2)3.0346 (15)150.6 (19)
O1B—H2O···O1Ai0.88 (2)2.04 (2)2.8973 (15)163 (2)
Symmetry code: (i) x+1/2, y1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1O···O1B0.89 (2)2.23 (2)3.0346 (15)150.6 (19)
O1B—H2O···O1Ai0.88 (2)2.04 (2)2.8973 (15)163 (2)
Symmetry code: (i) x+1/2, y1/2, z.
 

Acknowledgements

This work was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC).

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science
First citationBruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationJack, K., Fatila, E., Hillis, C. & Tam, W. (2013). Synth. Commun. 43, 1181–1187.  Web of Science CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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