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Acta Cryst. (2010). E66, o808-o809    [ doi:10.1107/S1600536810008524 ]

10,10-Dimethylanthrone

H.-K. Fun, M. Hemamalini, B. P. Siddaraju, H. S. Yathirajan and M. S. Siddegowda

Abstract top

In the title compound, C16H14O, the asymmetric unit consists of three crystallographically independent molecules. The anthracene units are essentially planar, with maximum deviations of 0.165 (1), 0.153 (1) and 0.045 (1) Å in the three molecules. In the crystal structure, molecules are linked via intermolecular C-H...O hydrogen bonds. Further stabilization is provided by C-H...[pi] interactions.

Comment top

Anthrone is a tricyclic aromatic hydrocarbon which is used for a popular cellulose assay and in the colorometric determination of carbohydrates (Trevelyan, 1952). The crystal structures of anthrone (Srivastava, 1964), 10-bromoanthrone (Destro et al., 1973), 9,10-dimethylanthracene (Iball & Low, 1974), benzylideneanthrone at 193 K (Ghosh et al., 1993), 10-(2-methylbenzylid- ene)anthrone (Zhou et al., 2004), 10-(3,4-dimethoxybenzylidene) anthrone (Zhou et al., 2005) and 10-(4-hydroxy-3-nitrobenzylidene) anthrone (Zhou et al., 2007), have been reported. In view of the importance of the title compound, (I), its crystal structure is reported here.

The asymmetric unit of the title compound, consists of three crystallographically independent 10,10-Dimethylanthrone molecules, (A, B & C), as shown in Fig. 1. The bond lengths and angles of molecules A , B and C agree with each other and are within normal ranges (Allen et al., 1987). The anthracene units are essentially planar with maximum deviations of 0.165 (1)Å for atom C3A (molecule A), 0.153 (1)Å for atom C14B (molecule B) and 0.045 (1)Å for atom C14C (molecule C). The two fused benzene rings, C1–C6 and C8–C13, make dihedral angles with the C1/C6–C8/C13–C14 plane of 5.74 (5)° and 3.85 (5)° in molecule A; 4.40 (6)° and 2.79 (6)° in molecule B; and 1.69 (6)° and 1.63 (6)° in molecule C.

In the crystal structure (Fig. 2), the molecules are linked through intermolecular C10—H10A···O1C, C10C—H10C···O1B, C3C—H3CA···O1A C15B—H15D···O1B and C16A—H16A···O1A hydrogen bonds. The structure is further stabilized by C—H···π interactions (Table 1), involving C1A–C6A (centroid Cg1), C1B–C6B (centroid Cg7), C1C–C6C (centroid Cg13) and C8C–C13C (centroid Cg15).

Related literature top

For analytical applications of the title compound, see: Trevelyan (1952). For related structures, see: Destro et al. (1973); Ghosh et al. (1993); Iball & Low (1974); Srivastava (1964); Zhou et al. (2004; 2005; 2007). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was obtained as a gift sample from R. L. Fine Chem, Bangalore, India. X-ray quality crystals were obtained by slow evaporation from a methanol solution (m. p.: 349–352 K).

Refinement top

All hydrogen atoms were positioned geometrically [C–H = 0.93 or 0.96Å] and were refined using a riding model, with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was applied to the methyl groups.

Computing details top

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

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms are omitted for clarity.
[Figure 2] Fig. 2. Crystal packing of the title compound, showing the hydrogen-bonding network (dashed lines). H atoms not involved in the hydrogen bond interactions are omitted for clarity.
10,10-Dimethyl-10H-anthracen-9-one top
Crystal data top
C16H14OZ = 6
Mr = 222.27F(000) = 708
Triclinic, P1Dx = 1.278 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.2438 (6) ÅCell parameters from 9906 reflections
b = 12.1105 (6) Åθ = 2.8–32.7°
c = 15.1025 (8) ŵ = 0.08 mm−1
α = 107.955 (1)°T = 100 K
β = 98.734 (1)°Block, orange
γ = 111.764 (1)°0.62 × 0.31 × 0.27 mm
V = 1732.47 (16) Å3
Data collection top
Bruker APEX DUO CCD area-detector
diffractometer		10016 independent reflections
Radiation source: fine-focus sealed tube8420 reflections with I > 2σ(I)
graphiteRint = 0.028
φ and ω scansθmax = 30.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −15→15
Tmin = 0.953, Tmax = 0.979k = −17→17
35076 measured reflectionsl = −21→21
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0807P)2 + 0.476P]
where P = (Fo2 + 2Fc2)/3
10016 reflections(Δ/σ)max = 0.001
466 parametersΔρmax = 0.54 e Å−3
0 restraintsΔρmin = −0.36 e Å−3
Crystal data top
C16H14Oγ = 111.764 (1)°
Mr = 222.27V = 1732.47 (16) Å3
Triclinic, P1Z = 6
a = 11.2438 (6) ÅMo Kα radiation
b = 12.1105 (6) ŵ = 0.08 mm−1
c = 15.1025 (8) ÅT = 100 K
α = 107.955 (1)°0.62 × 0.31 × 0.27 mm
β = 98.734 (1)°
Data collection top
Bruker APEX DUO CCD area-detector
diffractometer		10016 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		8420 reflections with I > 2σ(I)
Tmin = 0.953, Tmax = 0.979Rint = 0.028
35076 measured reflectionsθmax = 30.0°
Refinement top
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.142Δρmax = 0.54 e Å−3
S = 1.07Δρmin = −0.36 e Å−3
10016 reflectionsAbsolute structure: ?
466 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1A0.56816 (9)0.79013 (8)0.44954 (7)0.02699 (19)
C1A0.68614 (10)1.07682 (10)0.39587 (7)0.01479 (19)
C2A0.80724 (11)1.18655 (11)0.41974 (8)0.0192 (2)
H2AA0.80861.24740.39400.023*
C3A0.92550 (11)1.20656 (11)0.48111 (8)0.0218 (2)
H3AA1.00401.28140.49720.026*
C4A0.92729 (11)1.11539 (12)0.51856 (8)0.0218 (2)
H4AA1.00681.12780.55840.026*
C5A0.80939 (11)1.00627 (11)0.49582 (8)0.0194 (2)
H5AA0.80970.94470.52030.023*
C6A0.68883 (10)0.98739 (10)0.43599 (7)0.01541 (19)
C7A0.56463 (11)0.87236 (10)0.41915 (7)0.01671 (19)
C8A0.43582 (10)0.86035 (10)0.36546 (7)0.01535 (19)
C9A0.31622 (11)0.75993 (10)0.35921 (8)0.0189 (2)
H9AA0.32010.70450.38940.023*
C10A0.19306 (11)0.74253 (10)0.30882 (8)0.0210 (2)
H10A0.11410.67680.30580.025*
C11A0.18879 (11)0.82504 (11)0.26257 (9)0.0223 (2)
H11A0.10650.81370.22780.027*
C12A0.30651 (11)0.92392 (11)0.26805 (8)0.0209 (2)
H12A0.30180.97710.23580.025*
C13A0.43266 (10)0.94566 (10)0.32106 (7)0.01543 (19)
C14A0.55932 (10)1.05499 (10)0.32446 (7)0.01520 (19)
C15A0.57639 (12)1.01805 (12)0.22108 (8)0.0218 (2)
H15A0.58310.93780.20220.033*
H15B0.65651.08500.22150.033*
H15C0.50011.00850.17540.033*
C16A0.54310 (12)1.18059 (10)0.35169 (9)0.0216 (2)
H16A0.53601.20640.41670.032*
H16B0.46341.16620.30680.032*
H16C0.61981.24770.34860.032*
O1B0.52412 (9)0.74204 (9)0.03541 (7)0.02682 (19)
C1B0.69616 (10)0.58076 (10)−0.09660 (7)0.01525 (19)
C2B0.70059 (11)0.53353 (11)−0.19275 (8)0.0196 (2)
H2BA0.75810.4961−0.20620.023*
C3B0.62091 (12)0.54135 (11)−0.26839 (8)0.0226 (2)
H3BA0.62420.5077−0.33180.027*
C4B0.53651 (12)0.59936 (11)−0.24945 (8)0.0238 (2)
H4BA0.48420.6057−0.29980.029*
C5B0.53076 (11)0.64754 (11)−0.15537 (8)0.0210 (2)
H5BA0.47460.6868−0.14240.025*
C6B0.60928 (10)0.63766 (10)−0.07907 (8)0.01640 (19)
C7B0.59492 (10)0.68598 (10)0.01946 (8)0.01716 (19)
C8B0.66776 (10)0.66388 (10)0.09737 (8)0.01560 (19)
C9B0.64508 (11)0.69874 (10)0.18895 (8)0.0186 (2)
H9BA0.58410.73290.19830.022*
C10B0.71228 (12)0.68289 (11)0.26493 (8)0.0203 (2)
H10B0.69680.70610.32520.024*
C11B0.80371 (11)0.63168 (11)0.25022 (8)0.0195 (2)
H11B0.84960.62080.30100.023*
C12B0.82647 (11)0.59700 (10)0.16019 (8)0.0178 (2)
H12B0.88800.56340.15170.021*
C13B0.75874 (10)0.61140 (9)0.08158 (7)0.01495 (18)
C14B0.78902 (10)0.57404 (10)−0.01569 (7)0.01553 (19)
C15B0.77900 (13)0.43618 (11)−0.04709 (8)0.0236 (2)
H15D0.68800.3751−0.05990.035*
H15E0.83700.43220.00420.035*
H15F0.80570.4155−0.10510.035*
C16B0.93459 (11)0.67118 (12)−0.00016 (9)0.0234 (2)
H16D0.94180.75730.02050.035*
H16E0.95630.6495−0.06030.035*
H16F0.99580.66690.04900.035*
O1C0.95232 (9)0.45834 (8)0.29323 (7)0.0297 (2)
C1C1.10277 (10)0.24592 (9)0.31380 (7)0.01459 (18)
C2C1.20914 (11)0.25001 (10)0.37943 (8)0.0185 (2)
H2CA1.22810.17910.36440.022*
C3C1.28635 (12)0.35724 (11)0.46597 (8)0.0230 (2)
H3CA1.35580.35740.50830.028*
C4C1.26000 (13)0.46478 (11)0.48958 (8)0.0247 (2)
H4CA1.31110.53650.54790.030*
C5C1.15738 (12)0.46413 (10)0.42563 (8)0.0201 (2)
H5CA1.14020.53610.44080.024*
C6C1.07904 (10)0.35551 (9)0.33796 (7)0.01501 (19)
C7C0.97047 (10)0.36071 (10)0.27270 (8)0.01652 (19)
C8C0.88406 (10)0.24447 (10)0.18236 (7)0.01471 (18)
C9C0.77830 (11)0.24772 (11)0.12168 (8)0.0180 (2)
H9CA0.76600.32250.13880.022*
C10C0.69261 (11)0.14160 (12)0.03723 (8)0.0219 (2)
H10C0.62320.1445−0.00280.026*
C11C0.71192 (12)0.03012 (11)0.01295 (8)0.0226 (2)
H11C0.6544−0.0424−0.04340.027*
C12C0.81653 (11)0.02660 (11)0.07228 (8)0.0193 (2)
H12C0.8282−0.04850.05450.023*
C13C0.90527 (10)0.13340 (10)0.15846 (7)0.01460 (18)
C14C1.01912 (10)0.12450 (10)0.22050 (7)0.01462 (18)
C15C0.95875 (11)0.00734 (10)0.24858 (8)0.0194 (2)
H15G0.89800.01880.28480.029*
H15H1.02970.00130.28800.029*
H15I0.9111−0.07070.19040.029*
C16C1.11272 (11)0.10352 (11)0.15848 (8)0.0197 (2)
H16G1.14830.17510.13970.030*
H16H1.06270.02480.10110.030*
H16I1.18530.09770.19620.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0275 (4)0.0230 (4)0.0374 (5)0.0127 (4)0.0079 (4)0.0198 (4)
C1A0.0167 (5)0.0150 (4)0.0130 (4)0.0075 (4)0.0056 (3)0.0051 (3)
C2A0.0200 (5)0.0183 (5)0.0180 (5)0.0061 (4)0.0066 (4)0.0081 (4)
C3A0.0170 (5)0.0229 (5)0.0190 (5)0.0043 (4)0.0056 (4)0.0058 (4)
C4A0.0184 (5)0.0271 (6)0.0172 (5)0.0105 (4)0.0033 (4)0.0058 (4)
C5A0.0209 (5)0.0228 (5)0.0177 (5)0.0127 (4)0.0052 (4)0.0086 (4)
C6A0.0175 (5)0.0157 (4)0.0144 (4)0.0087 (4)0.0055 (3)0.0056 (4)
C7A0.0194 (5)0.0157 (4)0.0175 (4)0.0092 (4)0.0065 (4)0.0074 (4)
C8A0.0180 (5)0.0129 (4)0.0158 (4)0.0078 (4)0.0061 (3)0.0049 (3)
C9A0.0222 (5)0.0138 (4)0.0201 (5)0.0069 (4)0.0087 (4)0.0062 (4)
C10A0.0184 (5)0.0155 (5)0.0231 (5)0.0048 (4)0.0073 (4)0.0031 (4)
C11A0.0163 (5)0.0212 (5)0.0250 (5)0.0082 (4)0.0035 (4)0.0050 (4)
C12A0.0197 (5)0.0203 (5)0.0243 (5)0.0103 (4)0.0049 (4)0.0100 (4)
C13A0.0167 (5)0.0143 (4)0.0163 (4)0.0081 (4)0.0057 (4)0.0054 (4)
C14A0.0174 (5)0.0140 (4)0.0154 (4)0.0071 (4)0.0051 (3)0.0071 (3)
C15A0.0227 (5)0.0260 (5)0.0160 (5)0.0088 (4)0.0062 (4)0.0098 (4)
C16A0.0231 (5)0.0137 (5)0.0302 (6)0.0101 (4)0.0077 (4)0.0091 (4)
O1B0.0291 (4)0.0303 (5)0.0296 (4)0.0230 (4)0.0088 (3)0.0105 (4)
C1B0.0144 (4)0.0130 (4)0.0182 (4)0.0055 (4)0.0038 (3)0.0073 (4)
C2B0.0201 (5)0.0191 (5)0.0195 (5)0.0086 (4)0.0060 (4)0.0078 (4)
C3B0.0231 (5)0.0219 (5)0.0181 (5)0.0060 (4)0.0034 (4)0.0084 (4)
C4B0.0216 (5)0.0219 (5)0.0217 (5)0.0059 (4)−0.0016 (4)0.0096 (4)
C5B0.0174 (5)0.0182 (5)0.0257 (5)0.0078 (4)0.0014 (4)0.0091 (4)
C6B0.0146 (4)0.0130 (4)0.0205 (5)0.0058 (4)0.0030 (4)0.0066 (4)
C7B0.0159 (5)0.0145 (4)0.0215 (5)0.0078 (4)0.0046 (4)0.0069 (4)
C8B0.0146 (4)0.0124 (4)0.0193 (5)0.0058 (4)0.0051 (4)0.0058 (4)
C9B0.0189 (5)0.0156 (5)0.0227 (5)0.0089 (4)0.0087 (4)0.0067 (4)
C10B0.0241 (5)0.0176 (5)0.0193 (5)0.0088 (4)0.0092 (4)0.0068 (4)
C11B0.0204 (5)0.0189 (5)0.0184 (5)0.0079 (4)0.0044 (4)0.0080 (4)
C12B0.0169 (5)0.0177 (5)0.0207 (5)0.0090 (4)0.0057 (4)0.0084 (4)
C13B0.0137 (4)0.0124 (4)0.0178 (4)0.0050 (3)0.0050 (3)0.0056 (3)
C14B0.0157 (4)0.0165 (4)0.0176 (4)0.0095 (4)0.0059 (3)0.0076 (4)
C15B0.0354 (6)0.0232 (5)0.0222 (5)0.0209 (5)0.0113 (5)0.0106 (4)
C16B0.0154 (5)0.0323 (6)0.0236 (5)0.0090 (4)0.0069 (4)0.0139 (5)
O1C0.0302 (5)0.0166 (4)0.0363 (5)0.0140 (4)−0.0027 (4)0.0047 (3)
C1C0.0147 (4)0.0139 (4)0.0151 (4)0.0053 (4)0.0041 (3)0.0071 (3)
C2C0.0186 (5)0.0176 (5)0.0204 (5)0.0084 (4)0.0032 (4)0.0097 (4)
C3C0.0217 (5)0.0213 (5)0.0212 (5)0.0069 (4)−0.0018 (4)0.0096 (4)
C4C0.0271 (6)0.0174 (5)0.0193 (5)0.0053 (4)−0.0030 (4)0.0048 (4)
C5C0.0231 (5)0.0137 (4)0.0196 (5)0.0068 (4)0.0024 (4)0.0056 (4)
C6C0.0155 (4)0.0128 (4)0.0159 (4)0.0052 (4)0.0034 (3)0.0066 (4)
C7C0.0162 (5)0.0130 (4)0.0193 (5)0.0058 (4)0.0033 (4)0.0069 (4)
C8C0.0141 (4)0.0150 (4)0.0156 (4)0.0058 (4)0.0043 (3)0.0077 (4)
C9C0.0172 (5)0.0199 (5)0.0205 (5)0.0092 (4)0.0051 (4)0.0114 (4)
C10C0.0185 (5)0.0279 (6)0.0196 (5)0.0102 (4)0.0023 (4)0.0114 (4)
C11C0.0210 (5)0.0235 (5)0.0156 (5)0.0070 (4)0.0005 (4)0.0039 (4)
C12C0.0205 (5)0.0183 (5)0.0170 (5)0.0089 (4)0.0043 (4)0.0047 (4)
C13C0.0146 (4)0.0155 (4)0.0143 (4)0.0063 (4)0.0049 (3)0.0069 (4)
C14C0.0162 (4)0.0134 (4)0.0151 (4)0.0075 (4)0.0040 (3)0.0061 (3)
C15C0.0229 (5)0.0142 (4)0.0201 (5)0.0072 (4)0.0046 (4)0.0080 (4)
C16C0.0195 (5)0.0222 (5)0.0205 (5)0.0123 (4)0.0072 (4)0.0079 (4)
Geometric parameters (Å, °) top
O1A—C7A1.2286 (13)C9B—H9BA0.9300
C1A—C2A1.4013 (14)C10B—C11B1.3957 (16)
C1A—C6A1.4016 (14)C10B—H10B0.9300
C1A—C14A1.5309 (14)C11B—C12B1.3871 (15)
C2A—C3A1.3908 (16)C11B—H11B0.9300
C2A—H2AA0.9300C12B—C13B1.4040 (14)
C3A—C4A1.3920 (17)C12B—H12B0.9300
C3A—H3AA0.9300C13B—C14B1.5281 (14)
C4A—C5A1.3800 (16)C14B—C15B1.5430 (15)
C4A—H4AA0.9300C14B—C16B1.5503 (15)
C5A—C6A1.4061 (14)C15B—H15D0.9600
C5A—H5AA0.9300C15B—H15E0.9600
C6A—C7A1.4787 (14)C15B—H15F0.9600
C7A—C8A1.4800 (15)C16B—H16D0.9600
C8A—C13A1.4020 (14)C16B—H16E0.9600
C8A—C9A1.4051 (14)C16B—H16F0.9600
C9A—C10A1.3804 (16)O1C—C7C1.2280 (13)
C9A—H9AA0.9300C1C—C6C1.3998 (14)
C10A—C11A1.3945 (17)C1C—C2C1.4075 (14)
C10A—H10A0.9300C1C—C14C1.5254 (14)
C11A—C12A1.3867 (16)C2C—C3C1.3861 (15)
C11A—H11A0.9300C2C—H2CA0.9300
C12A—C13A1.4037 (15)C3C—C4C1.3939 (17)
C12A—H12A0.9300C3C—H3CA0.9300
C13A—C14A1.5235 (14)C4C—C5C1.3836 (16)
C14A—C16A1.5359 (14)C4C—H4CA0.9300
C14A—C15A1.5487 (14)C5C—C6C1.4043 (14)
C15A—H15A0.9600C5C—H5CA0.9300
C15A—H15B0.9600C6C—C7C1.4818 (14)
C15A—H15C0.9600C7C—C8C1.4786 (14)
C16A—H16A0.9600C8C—C13C1.4004 (14)
C16A—H16B0.9600C8C—C9C1.4076 (14)
C16A—H16C0.9600C9C—C10C1.3800 (15)
O1B—C7B1.2292 (13)C9C—H9CA0.9300
C1B—C6B1.4015 (14)C10C—C11C1.3931 (17)
C1B—C2B1.4032 (14)C10C—H10C0.9300
C1B—C14B1.5254 (14)C11C—C12C1.3889 (15)
C2B—C3B1.3912 (15)C11C—H11C0.9300
C2B—H2BA0.9300C12C—C13C1.4047 (14)
C3B—C4B1.3889 (17)C12C—H12C0.9300
C3B—H3BA0.9300C13C—C14C1.5260 (14)
C4B—C5B1.3814 (17)C14C—C15C1.5485 (14)
C4B—H4BA0.9300C14C—C16C1.5494 (14)
C5B—C6B1.4058 (14)C15C—H15G0.9600
C5B—H5BA0.9300C15C—H15H0.9600
C6B—C7B1.4795 (15)C15C—H15I0.9600
C7B—C8B1.4801 (14)C16C—H16G0.9600
C8B—C13B1.4035 (14)C16C—H16H0.9600
C8B—C9B1.4082 (14)C16C—H16I0.9600
C9B—C10B1.3801 (16)
C2A—C1A—C6A117.35 (10)C11B—C10B—H10B120.4
C2A—C1A—C14A120.03 (9)C12B—C11B—C10B120.30 (10)
C6A—C1A—C14A122.55 (9)C12B—C11B—H11B119.9
C3A—C2A—C1A121.50 (10)C10B—C11B—H11B119.9
C3A—C2A—H2AA119.3C11B—C12B—C13B121.56 (10)
C1A—C2A—H2AA119.3C11B—C12B—H12B119.2
C2A—C3A—C4A120.49 (10)C13B—C12B—H12B119.2
C2A—C3A—H3AA119.8C8B—C13B—C12B117.68 (9)
C4A—C3A—H3AA119.8C8B—C13B—C14B122.66 (9)
C5A—C4A—C3A119.08 (10)C12B—C13B—C14B119.63 (9)
C5A—C4A—H4AA120.5C1B—C14B—C13B113.08 (8)
C3A—C4A—H4AA120.5C1B—C14B—C15B109.74 (9)
C4A—C5A—C6A120.61 (10)C13B—C14B—C15B109.38 (8)
C4A—C5A—H5AA119.7C1B—C14B—C16B107.61 (8)
C6A—C5A—H5AA119.7C13B—C14B—C16B107.82 (8)
C1A—C6A—C5A120.93 (10)C15B—C14B—C16B109.10 (9)
C1A—C6A—C7A121.15 (9)C14B—C15B—H15D109.5
C5A—C6A—C7A117.90 (9)C14B—C15B—H15E109.5
O1A—C7A—C6A121.08 (10)H15D—C15B—H15E109.5
O1A—C7A—C8A121.12 (10)C14B—C15B—H15F109.5
C6A—C7A—C8A117.80 (9)H15D—C15B—H15F109.5
C13A—C8A—C9A120.68 (10)H15E—C15B—H15F109.5
C13A—C8A—C7A121.17 (9)C14B—C16B—H16D109.5
C9A—C8A—C7A118.15 (9)C14B—C16B—H16E109.5
C10A—C9A—C8A120.83 (10)H16D—C16B—H16E109.5
C10A—C9A—H9AA119.6C14B—C16B—H16F109.5
C8A—C9A—H9AA119.6H16D—C16B—H16F109.5
C9A—C10A—C11A119.01 (10)H16E—C16B—H16F109.5
C9A—C10A—H10A120.5C6C—C1C—C2C117.59 (9)
C11A—C10A—H10A120.5C6C—C1C—C14C122.92 (9)
C12A—C11A—C10A120.43 (10)C2C—C1C—C14C119.48 (9)
C12A—C11A—H11A119.8C3C—C2C—C1C121.57 (10)
C10A—C11A—H11A119.8C3C—C2C—H2CA119.2
C11A—C12A—C13A121.57 (10)C1C—C2C—H2CA119.2
C11A—C12A—H12A119.2C2C—C3C—C4C120.06 (10)
C13A—C12A—H12A119.2C2C—C3C—H3CA120.0
C8A—C13A—C12A117.44 (10)C4C—C3C—H3CA120.0
C8A—C13A—C14A122.81 (9)C5C—C4C—C3C119.55 (10)
C12A—C13A—C14A119.69 (9)C5C—C4C—H4CA120.2
C13A—C14A—C1A112.91 (8)C3C—C4C—H4CA120.2
C13A—C14A—C16A109.53 (8)C4C—C5C—C6C120.42 (10)
C1A—C14A—C16A109.86 (9)C4C—C5C—H5CA119.8
C13A—C14A—C15A107.85 (8)C6C—C5C—H5CA119.8
C1A—C14A—C15A107.88 (8)C1C—C6C—C5C120.78 (10)
C16A—C14A—C15A108.70 (9)C1C—C6C—C7C121.40 (9)
C14A—C15A—H15A109.5C5C—C6C—C7C117.82 (9)
C14A—C15A—H15B109.5O1C—C7C—C8C120.98 (10)
H15A—C15A—H15B109.5O1C—C7C—C6C121.04 (10)
C14A—C15A—H15C109.5C8C—C7C—C6C117.98 (9)
H15A—C15A—H15C109.5C13C—C8C—C9C120.82 (9)
H15B—C15A—H15C109.5C13C—C8C—C7C121.05 (9)
C14A—C16A—H16A109.5C9C—C8C—C7C118.12 (9)
C14A—C16A—H16B109.5C10C—C9C—C8C120.96 (10)
H16A—C16A—H16B109.5C10C—C9C—H9CA119.5
C14A—C16A—H16C109.5C8C—C9C—H9CA119.5
H16A—C16A—H16C109.5C9C—C10C—C11C118.83 (10)
H16B—C16A—H16C109.5C9C—C10C—H10C120.6
C6B—C1B—C2B117.54 (9)C11C—C10C—H10C120.6
C6B—C1B—C14B122.94 (9)C12C—C11C—C10C120.45 (10)
C2B—C1B—C14B119.46 (9)C12C—C11C—H11C119.8
C3B—C2B—C1B121.51 (10)C10C—C11C—H11C119.8
C3B—C2B—H2BA119.2C11C—C12C—C13C121.79 (10)
C1B—C2B—H2BA119.2C11C—C12C—H12C119.1
C4B—C3B—C2B120.13 (10)C13C—C12C—H12C119.1
C4B—C3B—H3BA119.9C8C—C13C—C12C117.14 (9)
C2B—C3B—H3BA119.9C8C—C13C—C14C123.28 (9)
C5B—C4B—C3B119.62 (10)C12C—C13C—C14C119.57 (9)
C5B—C4B—H4BA120.2C1C—C14C—C13C113.28 (8)
C3B—C4B—H4BA120.2C1C—C14C—C15C108.61 (8)
C4B—C5B—C6B120.39 (10)C13C—C14C—C15C108.91 (8)
C4B—C5B—H5BA119.8C1C—C14C—C16C108.38 (8)
C6B—C5B—H5BA119.8C13C—C14C—C16C108.09 (8)
C1B—C6B—C5B120.78 (10)C15C—C14C—C16C109.54 (8)
C1B—C6B—C7B121.12 (9)C14C—C15C—H15G109.5
C5B—C6B—C7B118.08 (9)C14C—C15C—H15H109.5
O1B—C7B—C6B120.70 (10)H15G—C15C—H15H109.5
O1B—C7B—C8B121.46 (10)C14C—C15C—H15I109.5
C6B—C7B—C8B117.83 (9)H15G—C15C—H15I109.5
C13B—C8B—C9B120.44 (10)H15H—C15C—H15I109.5
C13B—C8B—C7B121.31 (9)C14C—C16C—H16G109.5
C9B—C8B—C7B118.25 (9)C14C—C16C—H16H109.5
C10B—C9B—C8B120.80 (10)H16G—C16C—H16H109.5
C10B—C9B—H9BA119.6C14C—C16C—H16I109.5
C8B—C9B—H9BA119.6H16G—C16C—H16I109.5
C9B—C10B—C11B119.22 (10)H16H—C16C—H16I109.5
C9B—C10B—H10B120.4
C6A—C1A—C2A—C3A−0.26 (15)C8B—C9B—C10B—C11B0.04 (16)
C14A—C1A—C2A—C3A−177.26 (9)C9B—C10B—C11B—C12B−0.10 (16)
C1A—C2A—C3A—C4A1.80 (16)C10B—C11B—C12B—C13B−0.32 (16)
C2A—C3A—C4A—C5A−1.52 (16)C9B—C8B—C13B—C12B−0.83 (15)
C3A—C4A—C5A—C6A−0.26 (16)C7B—C8B—C13B—C12B178.22 (9)
C2A—C1A—C6A—C5A−1.52 (14)C9B—C8B—C13B—C14B−178.93 (9)
C14A—C1A—C6A—C5A175.40 (9)C7B—C8B—C13B—C14B0.12 (15)
C2A—C1A—C6A—C7A176.71 (9)C11B—C12B—C13B—C8B0.77 (15)
C14A—C1A—C6A—C7A−6.38 (14)C11B—C12B—C13B—C14B178.93 (10)
C4A—C5A—C6A—C1A1.81 (15)C6B—C1B—C14B—C13B10.95 (14)
C4A—C5A—C6A—C7A−176.48 (10)C2B—C1B—C14B—C13B−171.94 (9)
C1A—C6A—C7A—O1A175.70 (10)C6B—C1B—C14B—C15B133.38 (10)
C5A—C6A—C7A—O1A−6.02 (15)C2B—C1B—C14B—C15B−49.51 (12)
C1A—C6A—C7A—C8A−4.97 (14)C6B—C1B—C14B—C16B−108.02 (11)
C5A—C6A—C7A—C8A173.31 (9)C2B—C1B—C14B—C16B69.10 (12)
O1A—C7A—C8A—C13A−172.58 (10)C8B—C13B—C14B—C1B−8.51 (14)
C6A—C7A—C8A—C13A8.10 (14)C12B—C13B—C14B—C1B173.42 (9)
O1A—C7A—C8A—C9A6.77 (15)C8B—C13B—C14B—C15B−131.14 (10)
C6A—C7A—C8A—C9A−172.56 (9)C12B—C13B—C14B—C15B50.80 (12)
C13A—C8A—C9A—C10A0.37 (15)C8B—C13B—C14B—C16B110.33 (11)
C7A—C8A—C9A—C10A−178.98 (9)C12B—C13B—C14B—C16B−67.73 (12)
C8A—C9A—C10A—C11A1.02 (16)C6C—C1C—C2C—C3C1.30 (16)
C9A—C10A—C11A—C12A−0.68 (16)C14C—C1C—C2C—C3C−178.80 (10)
C10A—C11A—C12A—C13A−1.05 (17)C1C—C2C—C3C—C4C−0.35 (17)
C9A—C8A—C13A—C12A−2.02 (15)C2C—C3C—C4C—C5C−0.68 (18)
C7A—C8A—C13A—C12A177.31 (9)C3C—C4C—C5C—C6C0.72 (18)
C9A—C8A—C13A—C14A−179.17 (9)C2C—C1C—C6C—C5C−1.25 (15)
C7A—C8A—C13A—C14A0.16 (15)C14C—C1C—C6C—C5C178.85 (9)
C11A—C12A—C13A—C8A2.37 (16)C2C—C1C—C6C—C7C179.17 (9)
C11A—C12A—C13A—C14A179.62 (10)C14C—C1C—C6C—C7C−0.73 (15)
C8A—C13A—C14A—C1A−10.51 (13)C4C—C5C—C6C—C1C0.27 (16)
C12A—C13A—C14A—C1A172.40 (9)C4C—C5C—C6C—C7C179.86 (10)
C8A—C13A—C14A—C16A−133.28 (10)C1C—C6C—C7C—O1C−178.21 (10)
C12A—C13A—C14A—C16A49.63 (12)C5C—C6C—C7C—O1C2.20 (16)
C8A—C13A—C14A—C15A108.59 (11)C1C—C6C—C7C—C8C2.14 (14)
C12A—C13A—C14A—C15A−68.50 (12)C5C—C6C—C7C—C8C−177.45 (9)
C2A—C1A—C14A—C13A−169.52 (9)O1C—C7C—C8C—C13C179.49 (10)
C6A—C1A—C14A—C13A13.65 (13)C6C—C7C—C8C—C13C−0.86 (14)
C2A—C1A—C14A—C16A−46.94 (12)O1C—C7C—C8C—C9C−1.52 (15)
C6A—C1A—C14A—C16A136.23 (10)C6C—C7C—C8C—C9C178.13 (9)
C2A—C1A—C14A—C15A71.40 (12)C13C—C8C—C9C—C10C0.14 (16)
C6A—C1A—C14A—C15A−105.43 (11)C7C—C8C—C9C—C10C−178.85 (10)
C6B—C1B—C2B—C3B−0.66 (16)C8C—C9C—C10C—C11C0.35 (16)
C14B—C1B—C2B—C3B−177.93 (10)C9C—C10C—C11C—C12C−0.69 (17)
C1B—C2B—C3B—C4B1.40 (17)C10C—C11C—C12C—C13C0.55 (17)
C2B—C3B—C4B—C5B−0.92 (17)C9C—C8C—C13C—C12C−0.28 (14)
C3B—C4B—C5B—C6B−0.26 (17)C7C—C8C—C13C—C12C178.68 (9)
C2B—C1B—C6B—C5B−0.53 (15)C9C—C8C—C13C—C14C179.19 (9)
C14B—C1B—C6B—C5B176.64 (9)C7C—C8C—C13C—C14C−1.85 (15)
C2B—C1B—C6B—C7B177.92 (9)C11C—C12C—C13C—C8C−0.06 (15)
C14B—C1B—C6B—C7B−4.92 (15)C11C—C12C—C13C—C14C−179.55 (10)
C4B—C5B—C6B—C1B1.00 (16)C6C—C1C—C14C—C13C−1.78 (13)
C4B—C5B—C6B—C7B−177.50 (10)C2C—C1C—C14C—C13C178.33 (9)
C1B—C6B—C7B—O1B176.03 (10)C6C—C1C—C14C—C15C−122.91 (10)
C5B—C6B—C7B—O1B−5.48 (15)C2C—C1C—C14C—C15C57.19 (12)
C1B—C6B—C7B—C8B−4.30 (15)C6C—C1C—C14C—C16C118.17 (10)
C5B—C6B—C7B—C8B174.19 (9)C2C—C1C—C14C—C16C−61.73 (12)
O1B—C7B—C8B—C13B−173.65 (10)C8C—C13C—C14C—C1C3.08 (13)
C6B—C7B—C8B—C13B6.68 (14)C12C—C13C—C14C—C1C−177.46 (9)
O1B—C7B—C8B—C9B5.42 (15)C8C—C13C—C14C—C15C124.05 (10)
C6B—C7B—C8B—C9B−174.25 (9)C12C—C13C—C14C—C15C−56.49 (12)
C13B—C8B—C9B—C10B0.44 (16)C8C—C13C—C14C—C16C−117.03 (10)
C7B—C8B—C9B—C10B−178.64 (10)C12C—C13C—C14C—C16C62.43 (12)
Hydrogen-bond geometry (Å, °) top
Cg1, Cg7, Cg13 and Cg15 are the centroids of the C1A–C6A, C1B–C6B, C1C–C6C and C8C–C13C rings, respectively.
D—H···AD—HH···AD···AD—H···A
C10A—H10A···O1Ci0.932.523.4097 (16)160
C10C—H10C···O1Bii0.932.593.4374 (18)151
C3C—H3CA···O1Aiii0.932.453.2287 (17)141
C15B—H15D···O1Bii0.962.433.3568 (18)161
C16A—H16A···O1Aiv0.962.483.3934 (16)159
C3A—H3AA···Cg13v0.932.693.3996 (14)134
C3B—H3BA···Cg13vi0.932.773.3715 (14)123
C15A—H15B···Cg15v0.962.713.4915 (15)139
C15C—H15G···Cg1vii0.962.963.8656 (13)158
C16C—H16G···Cg7vi0.962.913.7432 (14)145
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+2, −z+1; (v) x, y+1, z; (vi) −x+2, −y+1, −z; (vii) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
Cg1, Cg7, Cg13 and Cg15 are the centroids of the C1A–C6A, C1B–C6B, C1C–C6C and C8C–C13C rings, respectively.
D—H···AD—HH···AD···AD—H···A
C10A—H10A···O1Ci0.932.523.4097 (16)160
C10C—H10C···O1Bii0.932.593.4374 (18)151
C3C—H3CA···O1Aiii0.932.453.2287 (17)141
C15B—H15D···O1Bii0.962.433.3568 (18)161
C16A—H16A···O1Aiv0.962.483.3934 (16)159
C3A—H3AA···Cg13v0.932.693.3996 (14)134
C3B—H3BA···Cg13vi0.932.773.3715 (14)123
C15A—H15B···Cg15v0.962.713.4915 (15)139
C15C—H15G···Cg1vii0.962.963.8656 (13)158
C16C—H16G···Cg7vi0.962.913.7432 (14)145
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+2, −z+1; (v) x, y+1, z; (vi) −x+2, −y+1, −z; (vii) x, y−1, z.
Acknowledgements top

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HSY thanks the University of Mysore for research facilities and for sabbatical leave.

references
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