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Acta Cryst. (2009). E65, o2168-o2169    [ doi:10.1107/S1600536809031900 ]

(Z)-3-(9-Anthryl)-1-(2-thienyl)prop-2-en-1-one

H.-K. Fun, T. Suwunwong, N. Boonnak and S. Chantrapromma

Abstract top

There are two crystallographically independent molecules in the asymmetric unit of the title heteroaryl chalcone, C21H14OS: the dihedral angle between the thiophene and anthracene rings is 75.07 (17)° in one molecule and 76.32 (17)° in the other. The crystal structure is consolidated by short C...O [3.348 (5)-3.394 (5) Å], C...S [3.607 (5)-3.666 (5) Å] and S...O [2.926 (3) Å] contacts, as well as by C-H...[pi] and [pi]-[pi] interactions [Cg...Cg = 3.745 (3) Å].

Comment top

Chalcones have been studied for their chemical and biological activities for a long time. They have a wide range of applications such as in non-linear optical (NLO) materials (Patil & Dharmaprakash, 2008), fluorescent materials (Svetlichny et al., 2007) and for showing various biological activities (Saydam et al., 2003). The anthracene moieties are well known for their high absorption co-efficients as well as their high fluorescence yields (Oliveira et al., 2007). These interesting properties has lead us to synthesize the title heteroaryl chalcone derivative, (I), which contains the donor sub-unit (anthracene) and fluorophore (thiophene) in order to study its NLO and fluorescent properties. We have previously synthesized and reported the crystal structures of chalcones and heteroaryl chalcone derivatives (Chantrapromma et al., 2009; Suwunwong et al., 2009a, b) which exist in the E configuartion. Herein, we report the crystal structure of the (I) which is in the Z configuration. Compound (I) crystallizes in the non-centrosymmetric orthorhombic space group Pna21 and therefore, it should exhibit second-order nonlinear optical properties. Moreover, (I) also shows interesting fluorescence properties which will be reported elsewhere.

The asymmetric unit of (I) contains two molecules, A and B, with the same configuration but with slight differences in bond lengths and angles. The molecule of (I)(Fig. 1) exists in an Z configuration with respect to the C15=C16 double bond [1.360 (6) Å in molecule A and 1.331 (6) Å in molecule B]; the C14–C15–C16–C17 torsion angle = -3.7 (7)° in molecule A [-4.0 (7)° in molecule B]. The anthracene unit is essentially planar with the greatest deviation of 0.089 (5) Å at atom C11A [0.086 (5)Å at atom C3B]. The total molecule is twisted as the interplanar angle between thiophene and anthracene rings is 75.07 (17)° and the mean plane through the prop-2-en-1-one unit (C15–C17/O1) makes interplanar angles of 13.1 (3) and 71.2 (3)° with the thiophene and anthracene rings, respectively [the corresponding values are 76.32 (17), 15.2 (3) and 72.3 (3)° in molecule B]. The bond distances are comparable with related structures (Chantrapromma et al., 2009; Suwunwong et al., 2009a, b).

In the crystal packing, the molecules are connected by short C···O [3.348 (5)–3.394 (5) Å], C···S [3.607 (5)–3.666 (5) Å], and S···O [2.926 (3) Å] contacts. The crystal structure is further stabilized by C—H···π interactions (Table 1) and π–π interactions with the Cg1···Cg4i distance being 3.745 (3) Å (i: 1/2 + x, -y + 1/2, z); Cg1 and Cg4 are the centroids of the S1A/C18A–C21A and S1B/C18B–C21B rings, respectively.

Related literature top

For related structures, see: Chantrapromma et al. (2009); Suwunwong et al. (2009a,b). For background to and applications of chalcones, see: Oliveira et al. (2007); Patil & Dharmaprakash (2008); Saydam et al. (2003); Svetlichny et al. (2007). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986). Cg1, Cg2, Cg3, Cg4, Cg5 and Cg6 are the centroids of the S1A/C18A–C21A, C1A–C6A, C8A–C13A, S1B/C18B–C21B, C1B–C6B and C8B–C13B rings, respectively.

Experimental top

Compound (I) was synthesized by the condensation of anthracene-9-carbaldehyde (2 mmol, 0.41 g) with 2-acetylthiophene (2 mmol, 0.22 ml) in ethanol (30 ml) in the presence of NaOH (5 ml, 30 %). After stirring for 2 h, a yellow solid appeared which was then collected by filtration, washed with distilled water, dried and purified by repeated recrystallization using ethanol/acetone in a 1:5 ratio as solvent. Orange block-shaped crystals of (I) were obtained from hot ethanol by the slow evaporation of the solvent held at room temperature for several days; M.p. 391–392 K.

Refinement top

All H atoms were placed in calculated positions with C—H = 0.93 Å and Uiso = 1.2Ueq(C). The highest residual electron density peak was located 0.14 Å from atom C19B and the deepest hole was located 0.48 Å from atom S1B.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
(Z)-3-(9-Anthryl)-1-(2-thienyl)prop-2-en-1-one top
Crystal data top
C21H14OSDx = 1.361 Mg m−3
Mr = 314.39Melting point = 391–392 K
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 6662 reflections
a = 14.6675 (2) Åθ = 1.1–27.5°
b = 5.5096 (1) ŵ = 0.21 mm−1
c = 37.9823 (4) ÅT = 100 K
V = 3069.43 (8) Å3Block, orange
Z = 80.30 × 0.12 × 0.10 mm
F(000) = 1312
Data collection top
Bruker APEXII CCD area-detector
diffractometer		6662 independent reflections
Radiation source: sealed tube5348 reflections with I > 2σ(I)
graphiteRint = 0.055
φ and ω scansθmax = 27.5°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −19→18
Tmin = 0.939, Tmax = 0.979k = −7→7
28929 measured reflectionsl = −49→49
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)] = 0.065H-atom parameters constrained
wR(F2) = 0.200 w = 1/[σ2(Fo2) + (0.1247P)2 + 2.1057P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
6662 reflectionsΔρmax = 1.58 e Å−3
391 parametersΔρmin = −0.82 e Å−3
1 restraintAbsolute structure: Flack (1983), 3093 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.09 (15)
Crystal data top
C21H14OSV = 3069.43 (8) Å3
Mr = 314.39Z = 8
Orthorhombic, Pna21Mo Kα radiation
a = 14.6675 (2) ŵ = 0.21 mm−1
b = 5.5096 (1) ÅT = 100 K
c = 37.9823 (4) Å0.30 × 0.12 × 0.10 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		6662 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		5348 reflections with I > 2σ(I)
Tmin = 0.939, Tmax = 0.979Rint = 0.055
28929 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.065H-atom parameters constrained
wR(F2) = 0.200Δρmax = 1.58 e Å−3
S = 1.06Δρmin = −0.82 e Å−3
6662 reflectionsAbsolute structure: Flack (1983), 3093 Friedel pairs
391 parametersFlack parameter: 0.09 (15)
1 restraint
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 120.0 (1) 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) top
xyzUiso*/Ueq
S1A0.80198 (8)−0.2591 (2)0.30703 (3)0.0253 (3)
O1A0.7762 (2)−0.1293 (6)0.38105 (8)0.0233 (7)
C1A0.7530 (3)0.1889 (8)0.46578 (11)0.0157 (8)
C2A0.8200 (3)0.3771 (8)0.46638 (11)0.0201 (9)
H2AA0.82390.48400.44750.024*
C3A0.8784 (3)0.4033 (9)0.49401 (12)0.0252 (10)
H3AA0.92040.52980.49420.030*
C4A0.8750 (3)0.2366 (9)0.52269 (13)0.0262 (10)
H4AA0.91570.25330.54130.031*
C5A0.8129 (3)0.0531 (9)0.52310 (11)0.0227 (9)
H5AA0.8121−0.05440.54200.027*
C6A0.7491 (3)0.0228 (8)0.49507 (11)0.0189 (9)
C7A0.6846 (3)−0.1604 (8)0.49469 (11)0.0200 (9)
H7AA0.6840−0.27120.51320.024*
C8A0.6203 (3)−0.1866 (8)0.46777 (11)0.0176 (9)
C9A0.5528 (3)−0.3732 (9)0.46845 (13)0.0240 (10)
H9AA0.5526−0.48590.48670.029*
C10A0.4888 (3)−0.3872 (9)0.44255 (12)0.0263 (10)
H10A0.4447−0.50850.44330.032*
C11A0.4888 (3)−0.2184 (10)0.41446 (13)0.0264 (11)
H11A0.4438−0.22680.39730.032*
C12A0.5540 (3)−0.0448 (8)0.41243 (11)0.0195 (9)
H12A0.55390.06090.39330.023*
C13A0.6233 (3)−0.0193 (8)0.43891 (10)0.0173 (8)
C14A0.6914 (3)0.1587 (8)0.43721 (10)0.0153 (8)
C15A0.6981 (3)0.3295 (8)0.40749 (11)0.0186 (9)
H15A0.68510.49140.41230.022*
C16A0.7215 (3)0.2743 (8)0.37378 (12)0.0172 (9)
H16A0.71960.39900.35730.021*
C17A0.7496 (3)0.0316 (8)0.36137 (11)0.0169 (9)
C18A0.7486 (3)−0.0075 (8)0.32292 (11)0.0156 (8)
C19A0.7103 (3)0.1397 (9)0.29449 (11)0.0176 (5)
H19A0.67890.28510.29730.021*
C20A0.7287 (3)0.0241 (8)0.26182 (11)0.0176 (5)
H20A0.70940.08590.24030.021*
C21A0.7784 (3)−0.1906 (9)0.26501 (11)0.0176 (5)
H21A0.7964−0.28510.24600.021*
S1B0.45484 (8)0.2512 (2)0.28505 (3)0.0222 (3)
O1B0.4761 (2)0.3719 (5)0.20988 (8)0.0224 (7)
C1B0.4998 (3)0.6562 (8)0.12502 (11)0.0163 (8)
C2B0.4294 (3)0.8335 (9)0.12167 (11)0.0201 (9)
H2BA0.42360.95380.13870.024*
C3B0.3701 (3)0.8295 (8)0.09376 (12)0.0218 (9)
H3BA0.32560.94900.09170.026*
C4B0.3764 (3)0.6446 (9)0.06824 (12)0.0225 (9)
H4BA0.33530.64220.04960.027*
C5B0.4412 (3)0.4706 (8)0.07042 (11)0.0198 (9)
H5BA0.44350.34910.05340.024*
C6B0.5066 (3)0.4707 (8)0.09854 (10)0.0152 (8)
C7B0.5750 (3)0.2983 (8)0.10025 (11)0.0181 (9)
H7BA0.57760.17620.08340.022*
C8B0.6408 (3)0.3054 (8)0.12722 (11)0.0174 (9)
C9B0.7149 (3)0.1350 (8)0.12850 (12)0.0217 (9)
H9BA0.71900.01420.11150.026*
C10B0.7797 (3)0.1477 (9)0.15438 (13)0.0268 (10)
H10B0.82720.03610.15480.032*
C11B0.7745 (3)0.3299 (9)0.18054 (12)0.0230 (10)
H11B0.81940.33840.19780.028*
C12B0.7041 (3)0.4945 (9)0.18086 (12)0.0198 (9)
H12B0.70160.61190.19840.024*
C13B0.6343 (3)0.4872 (8)0.15435 (10)0.0157 (8)
C14B0.5611 (3)0.6550 (8)0.15328 (11)0.0150 (8)
C15B0.5492 (3)0.8349 (8)0.18238 (12)0.0181 (9)
H15B0.55870.99760.17700.022*
C16B0.5261 (3)0.7810 (8)0.21535 (12)0.0169 (9)
H16B0.52470.90860.23140.020*
C17B0.5024 (3)0.5369 (8)0.22900 (11)0.0163 (8)
C18B0.5063 (3)0.5004 (8)0.26765 (12)0.0180 (8)
C19B0.5461 (3)0.6449 (9)0.29485 (11)0.0186 (5)
H19B0.57740.78950.29110.022*
C20B0.5319 (3)0.5402 (8)0.32761 (11)0.0186 (5)
H20B0.55380.60750.34840.022*
C21B0.4834 (3)0.3311 (9)0.32663 (11)0.0186 (5)
H21B0.46750.24200.34650.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0264 (6)0.0243 (7)0.0251 (6)−0.0017 (5)0.0031 (5)−0.0036 (5)
O1A0.0312 (17)0.0193 (17)0.0194 (14)0.0059 (14)0.0025 (13)0.0055 (14)
C1A0.0149 (19)0.016 (2)0.0165 (19)0.0051 (16)0.0006 (15)−0.0002 (18)
C2A0.022 (2)0.019 (2)0.0196 (19)0.0016 (17)0.0055 (16)0.0007 (19)
C3A0.021 (2)0.025 (2)0.030 (2)−0.0011 (18)−0.0034 (18)−0.006 (2)
C4A0.024 (2)0.030 (3)0.024 (2)0.0028 (19)−0.0063 (18)−0.008 (2)
C5A0.025 (2)0.027 (2)0.0158 (18)0.0093 (19)−0.0007 (17)−0.0011 (19)
C6A0.021 (2)0.021 (2)0.0150 (18)0.0088 (17)0.0036 (16)−0.0006 (18)
C7A0.023 (2)0.021 (2)0.0162 (19)0.0065 (18)0.0027 (16)0.0061 (19)
C8A0.0172 (19)0.015 (2)0.021 (2)0.0031 (16)0.0082 (16)−0.0008 (19)
C9A0.026 (2)0.017 (2)0.029 (2)−0.0006 (17)0.0103 (18)0.002 (2)
C10A0.026 (2)0.023 (2)0.030 (2)−0.0091 (19)0.0108 (18)−0.006 (2)
C11A0.018 (2)0.036 (3)0.025 (2)0.0000 (19)−0.0004 (17)−0.010 (2)
C12A0.024 (2)0.020 (2)0.0147 (19)0.0038 (17)0.0001 (16)0.0000 (19)
C13A0.019 (2)0.019 (2)0.0134 (18)0.0019 (17)−0.0010 (15)−0.0045 (18)
C14A0.023 (2)0.013 (2)0.0103 (18)0.0027 (16)0.0032 (15)−0.0018 (17)
C15A0.027 (2)0.013 (2)0.016 (2)−0.0008 (16)0.0002 (16)−0.0055 (19)
C16A0.022 (2)0.014 (2)0.016 (2)0.0029 (17)−0.0010 (18)0.0068 (17)
C17A0.0174 (19)0.014 (2)0.019 (2)−0.0061 (16)0.0048 (15)0.0018 (18)
C18A0.0151 (18)0.016 (2)0.0156 (17)−0.0043 (15)0.0055 (15)−0.0018 (17)
C19A0.0125 (11)0.0246 (13)0.0158 (11)−0.0094 (10)0.0020 (9)−0.0044 (11)
C20A0.0125 (11)0.0246 (13)0.0158 (11)−0.0094 (10)0.0020 (9)−0.0044 (11)
C21A0.0125 (11)0.0246 (13)0.0158 (11)−0.0094 (10)0.0020 (9)−0.0044 (11)
S1B0.0233 (6)0.0204 (6)0.0230 (6)0.0010 (4)0.0023 (4)0.0046 (5)
O1B0.0306 (17)0.0165 (16)0.0200 (14)−0.0019 (13)0.0020 (13)−0.0011 (14)
C1B0.019 (2)0.014 (2)0.0161 (19)0.0011 (16)0.0065 (15)0.0049 (18)
C2B0.022 (2)0.022 (2)0.0166 (19)0.0012 (18)0.0014 (16)0.0026 (18)
C3B0.019 (2)0.020 (2)0.026 (2)0.0002 (17)−0.0013 (17)0.007 (2)
C4B0.020 (2)0.028 (3)0.0185 (19)−0.0049 (19)−0.0027 (16)0.001 (2)
C5B0.024 (2)0.021 (2)0.0141 (18)−0.0022 (17)−0.0021 (16)0.0000 (18)
C6B0.0152 (19)0.018 (2)0.0122 (17)−0.0054 (15)0.0011 (15)−0.0010 (17)
C7B0.021 (2)0.020 (2)0.0133 (18)−0.0024 (17)0.0062 (16)−0.0033 (18)
C8B0.019 (2)0.017 (2)0.016 (2)0.0006 (17)0.0050 (16)0.0041 (18)
C9B0.020 (2)0.019 (2)0.026 (2)0.0022 (17)0.0098 (17)−0.001 (2)
C10B0.024 (2)0.026 (3)0.031 (2)0.007 (2)0.0083 (19)0.008 (2)
C11B0.020 (2)0.028 (3)0.022 (2)0.0023 (19)0.0002 (17)0.009 (2)
C12B0.020 (2)0.021 (2)0.019 (2)0.0012 (17)−0.0006 (16)0.0012 (18)
C13B0.0178 (19)0.014 (2)0.0151 (18)0.0009 (16)0.0059 (15)0.0005 (18)
C14B0.0174 (19)0.012 (2)0.0160 (18)−0.0009 (16)0.0016 (15)0.0015 (18)
C15B0.0163 (19)0.014 (2)0.024 (2)−0.0019 (15)0.0031 (16)−0.002 (2)
C16B0.023 (2)0.014 (2)0.014 (2)−0.0007 (17)0.0004 (18)−0.0044 (17)
C17B0.0171 (19)0.017 (2)0.0147 (18)−0.0021 (16)0.0040 (15)−0.0011 (18)
C18B0.0157 (18)0.017 (2)0.021 (2)0.0030 (16)0.0051 (16)−0.0023 (18)
C19B0.0145 (11)0.0243 (14)0.0171 (11)0.0086 (10)0.0017 (9)0.0021 (11)
C20B0.0145 (11)0.0243 (14)0.0171 (11)0.0086 (10)0.0017 (9)0.0021 (11)
C21B0.0145 (11)0.0243 (14)0.0171 (11)0.0086 (10)0.0017 (9)0.0021 (11)
Geometric parameters (Å, °) top
S1A—C21A1.676 (4)S1B—C21B1.692 (5)
S1A—C18A1.703 (4)S1B—C18B1.700 (5)
O1A—C17A1.224 (5)O1B—C17B1.226 (5)
C1A—C14A1.422 (6)C1B—C14B1.400 (6)
C1A—C2A1.430 (6)C1B—C2B1.427 (6)
C1A—C6A1.442 (6)C1B—C6B1.438 (6)
C2A—C3A1.362 (6)C2B—C3B1.372 (6)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.426 (7)C3B—C4B1.409 (7)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.361 (7)C4B—C5B1.353 (6)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.428 (6)C5B—C6B1.435 (5)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—C7A1.383 (6)C6B—C7B1.383 (6)
C7A—C8A1.398 (6)C7B—C8B1.408 (6)
C7A—H7AA0.9300C7B—H7BA0.9300
C8A—C9A1.427 (6)C8B—C9B1.437 (6)
C8A—C13A1.433 (6)C8B—C13B1.440 (6)
C9A—C10A1.362 (7)C9B—C10B1.368 (7)
C9A—H9AA0.9300C9B—H9BA0.9300
C10A—C11A1.415 (7)C10B—C11B1.415 (7)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.354 (7)C11B—C12B1.374 (6)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.437 (5)C12B—C13B1.436 (5)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.401 (6)C13B—C14B1.417 (6)
C14A—C15A1.473 (6)C14B—C15B1.495 (6)
C15A—C16A1.360 (6)C15B—C16B1.331 (6)
C15A—H15A0.9300C15B—H15B0.9300
C16A—C17A1.477 (6)C16B—C17B1.483 (6)
C16A—H16A0.9300C16B—H16B0.9300
C17A—C18A1.476 (5)C17B—C18B1.483 (6)
C18A—C19A1.463 (6)C18B—C19B1.430 (6)
C19A—C20A1.421 (6)C19B—C20B1.387 (6)
C19A—H19A0.9300C19B—H19B0.9300
C20A—C21A1.395 (6)C20B—C21B1.355 (7)
C20A—H20A0.9300C20B—H20B0.9300
C21A—H21A0.9300C21B—H21B0.9300
C21A—S1A—C18A93.4 (2)C21B—S1B—C18B92.5 (2)
C14A—C1A—C2A122.3 (4)C14B—C1B—C2B122.4 (4)
C14A—C1A—C6A119.3 (4)C14B—C1B—C6B119.2 (4)
C2A—C1A—C6A118.4 (4)C2B—C1B—C6B118.3 (4)
C3A—C2A—C1A121.5 (4)C3B—C2B—C1B121.1 (4)
C3A—C2A—H2AA119.3C3B—C2B—H2BA119.4
C1A—C2A—H2AA119.3C1B—C2B—H2BA119.4
C2A—C3A—C4A119.9 (4)C2B—C3B—C4B120.1 (4)
C2A—C3A—H3AA120.1C2B—C3B—H3BA120.0
C4A—C3A—H3AA120.1C4B—C3B—H3BA120.0
C5A—C4A—C3A120.7 (4)C5B—C4B—C3B121.1 (4)
C5A—C4A—H4AA119.6C5B—C4B—H4BA119.4
C3A—C4A—H4AA119.6C3B—C4B—H4BA119.4
C4A—C5A—C6A121.2 (4)C4B—C5B—C6B121.0 (4)
C4A—C5A—H5AA119.4C4B—C5B—H5BA119.5
C6A—C5A—H5AA119.4C6B—C5B—H5BA119.5
C7A—C6A—C5A122.8 (4)C7B—C6B—C5B121.3 (4)
C7A—C6A—C1A118.8 (4)C7B—C6B—C1B120.4 (4)
C5A—C6A—C1A118.4 (4)C5B—C6B—C1B118.3 (4)
C6A—C7A—C8A122.9 (4)C6B—C7B—C8B120.8 (4)
C6A—C7A—H7AA118.5C6B—C7B—H7BA119.6
C8A—C7A—H7AA118.5C8B—C7B—H7BA119.6
C7A—C8A—C9A121.9 (4)C7B—C8B—C9B121.7 (4)
C7A—C8A—C13A118.2 (4)C7B—C8B—C13B119.6 (4)
C9A—C8A—C13A119.9 (4)C9B—C8B—C13B118.7 (4)
C10A—C9A—C8A120.4 (4)C10B—C9B—C8B121.1 (4)
C10A—C9A—H9AA119.8C10B—C9B—H9BA119.5
C8A—C9A—H9AA119.8C8B—C9B—H9BA119.5
C9A—C10A—C11A120.5 (4)C9B—C10B—C11B120.2 (4)
C9A—C10A—H10A119.8C9B—C10B—H10B119.9
C11A—C10A—H10A119.8C11B—C10B—H10B119.9
C12A—C11A—C10A120.5 (4)C12B—C11B—C10B121.0 (4)
C12A—C11A—H11A119.8C12B—C11B—H11B119.5
C10A—C11A—H11A119.8C10B—C11B—H11B119.5
C11A—C12A—C13A121.9 (4)C11B—C12B—C13B120.7 (4)
C11A—C12A—H12A119.0C11B—C12B—H12B119.6
C13A—C12A—H12A119.0C13B—C12B—H12B119.6
C14A—C13A—C8A120.5 (4)C14B—C13B—C12B122.8 (4)
C14A—C13A—C12A122.7 (4)C14B—C13B—C8B118.9 (4)
C8A—C13A—C12A116.8 (4)C12B—C13B—C8B118.3 (4)
C13A—C14A—C1A120.0 (4)C1B—C14B—C13B120.8 (4)
C13A—C14A—C15A122.0 (4)C1B—C14B—C15B119.2 (4)
C1A—C14A—C15A117.9 (4)C13B—C14B—C15B120.0 (4)
C16A—C15A—C14A126.6 (4)C16B—C15B—C14B125.3 (4)
C16A—C15A—H15A116.7C16B—C15B—H15B117.4
C14A—C15A—H15A116.7C14B—C15B—H15B117.4
C15A—C16A—C17A125.0 (4)C15B—C16B—C17B126.2 (4)
C15A—C16A—H16A117.5C15B—C16B—H16B116.9
C17A—C16A—H16A117.5C17B—C16B—H16B116.9
O1A—C17A—C18A120.1 (4)O1B—C17B—C18B119.9 (4)
O1A—C17A—C16A123.4 (4)O1B—C17B—C16B122.6 (4)
C18A—C17A—C16A116.4 (4)C18B—C17B—C16B117.4 (4)
C19A—C18A—C17A130.8 (4)C19B—C18B—C17B131.0 (4)
C19A—C18A—S1A111.5 (3)C19B—C18B—S1B110.5 (3)
C17A—C18A—S1A117.7 (3)C17B—C18B—S1B118.5 (3)
C20A—C19A—C18A108.9 (4)C20B—C19B—C18B110.8 (4)
C20A—C19A—H19A125.6C20B—C19B—H19B124.6
C18A—C19A—H19A125.6C18B—C19B—H19B124.6
C21A—C20A—C19A113.8 (4)C21B—C20B—C19B114.1 (4)
C21A—C20A—H20A123.1C21B—C20B—H20B123.0
C19A—C20A—H20A123.1C19B—C20B—H20B123.0
C20A—C21A—S1A112.4 (3)C20B—C21B—S1B112.1 (3)
C20A—C21A—H21A123.8C20B—C21B—H21B123.9
S1A—C21A—H21A123.8S1B—C21B—H21B123.9
C14A—C1A—C2A—C3A179.9 (4)C14B—C1B—C2B—C3B−179.7 (4)
C6A—C1A—C2A—C3A−0.9 (6)C6B—C1B—C2B—C3B−0.7 (6)
C1A—C2A—C3A—C4A1.8 (7)C1B—C2B—C3B—C4B1.7 (7)
C2A—C3A—C4A—C5A−1.1 (7)C2B—C3B—C4B—C5B−0.9 (7)
C3A—C4A—C5A—C6A−0.4 (7)C3B—C4B—C5B—C6B−0.9 (7)
C4A—C5A—C6A—C7A−179.6 (4)C4B—C5B—C6B—C7B−177.7 (4)
C4A—C5A—C6A—C1A1.2 (6)C4B—C5B—C6B—C1B1.9 (6)
C14A—C1A—C6A—C7A−0.7 (6)C14B—C1B—C6B—C7B−2.4 (6)
C2A—C1A—C6A—C7A−179.8 (4)C2B—C1B—C6B—C7B178.5 (4)
C14A—C1A—C6A—C5A178.6 (4)C14B—C1B—C6B—C5B178.0 (4)
C2A—C1A—C6A—C5A−0.6 (6)C2B—C1B—C6B—C5B−1.1 (6)
C5A—C6A—C7A—C8A178.2 (4)C5B—C6B—C7B—C8B177.6 (4)
C1A—C6A—C7A—C8A−2.6 (6)C1B—C6B—C7B—C8B−2.0 (6)
C6A—C7A—C8A—C9A−178.3 (4)C6B—C7B—C8B—C9B−177.0 (4)
C6A—C7A—C8A—C13A1.7 (6)C6B—C7B—C8B—C13B3.0 (6)
C7A—C8A—C9A—C10A177.2 (4)C7B—C8B—C9B—C10B178.4 (4)
C13A—C8A—C9A—C10A−2.7 (6)C13B—C8B—C9B—C10B−1.6 (6)
C8A—C9A—C10A—C11A0.6 (7)C8B—C9B—C10B—C11B0.1 (7)
C9A—C10A—C11A—C12A1.8 (7)C9B—C10B—C11B—C12B1.0 (7)
C10A—C11A—C12A—C13A−2.1 (7)C10B—C11B—C12B—C13B−0.6 (7)
C7A—C8A—C13A—C14A2.6 (6)C11B—C12B—C13B—C14B−179.1 (4)
C9A—C8A—C13A—C14A−177.4 (4)C11B—C12B—C13B—C8B−0.8 (6)
C7A—C8A—C13A—C12A−177.5 (4)C7B—C8B—C13B—C14B0.3 (6)
C9A—C8A—C13A—C12A2.4 (6)C9B—C8B—C13B—C14B−179.7 (4)
C11A—C12A—C13A—C14A179.8 (4)C7B—C8B—C13B—C12B−178.1 (4)
C11A—C12A—C13A—C8A−0.1 (6)C9B—C8B—C13B—C12B1.9 (6)
C8A—C13A—C14A—C1A−5.9 (6)C2B—C1B—C14B—C13B−175.3 (4)
C12A—C13A—C14A—C1A174.3 (4)C6B—C1B—C14B—C13B5.7 (6)
C8A—C13A—C14A—C15A178.3 (4)C2B—C1B—C14B—C15B4.2 (6)
C12A—C13A—C14A—C15A−1.5 (6)C6B—C1B—C14B—C15B−174.8 (4)
C2A—C1A—C14A—C13A−176.0 (4)C12B—C13B—C14B—C1B173.6 (4)
C6A—C1A—C14A—C13A4.8 (6)C8B—C13B—C14B—C1B−4.7 (6)
C2A—C1A—C14A—C15A0.0 (6)C12B—C13B—C14B—C15B−5.9 (6)
C6A—C1A—C14A—C15A−179.2 (4)C8B—C13B—C14B—C15B175.9 (4)
C13A—C14A—C15A—C16A−68.5 (6)C1B—C14B—C15B—C16B112.9 (5)
C1A—C14A—C15A—C16A115.5 (5)C13B—C14B—C15B—C16B−67.7 (6)
C14A—C15A—C16A—C17A−3.7 (7)C14B—C15B—C16B—C17B−4.0 (7)
C15A—C16A—C17A—O1A−18.5 (7)C15B—C16B—C17B—O1B−21.8 (7)
C15A—C16A—C17A—C18A164.3 (4)C15B—C16B—C17B—C18B161.7 (4)
O1A—C17A—C18A—C19A171.3 (4)O1B—C17B—C18B—C19B169.3 (4)
C16A—C17A—C18A—C19A−11.4 (6)C16B—C17B—C18B—C19B−14.0 (7)
O1A—C17A—C18A—S1A−10.4 (5)O1B—C17B—C18B—S1B−11.8 (5)
C16A—C17A—C18A—S1A166.9 (3)C16B—C17B—C18B—S1B164.8 (3)
C21A—S1A—C18A—C19A−0.1 (3)C21B—S1B—C18B—C19B0.3 (3)
C21A—S1A—C18A—C17A−178.7 (3)C21B—S1B—C18B—C17B−178.8 (3)
C17A—C18A—C19A—C20A179.1 (4)C17B—C18B—C19B—C20B179.2 (4)
S1A—C18A—C19A—C20A0.7 (4)S1B—C18B—C19B—C20B0.3 (4)
C18A—C19A—C20A—C21A−1.1 (5)C18B—C19B—C20B—C21B−1.0 (5)
C19A—C20A—C21A—S1A1.0 (4)C19B—C20B—C21B—S1B1.2 (5)
C18A—S1A—C21A—C20A−0.5 (3)C18B—S1B—C21B—C20B−0.8 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C3A—H3AA···Cg3i0.932.993.679 (5)132
C10A—H10A···Cg2ii0.932.953.694 (5)138
C10B—H10B···Cg5i0.932.933.594 (5)129
C15A—H15A···Cg3iii0.932.763.550 (5)143
C15B—H15B···Cg6iii0.932.943.689 (5)139
C19A—H19A···Cg40.932.723.486 (5)140
C19B—H19B···Cg1iii0.932.723.458 (5)137
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) x−1/2, −y−1/2, z; (iii) x, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C3A—H3AA···Cg3i0.932.993.679 (5)132
C10A—H10A···Cg2ii0.932.953.694 (5)138
C10B—H10B···Cg5i0.932.933.594 (5)129
C15A—H15A···Cg3iii0.932.763.550 (5)143
C15B—H15B···Cg6iii0.932.943.689 (5)139
C19A—H19A···Cg40.932.723.486 (5)140
C19B—H19B···Cg1iii0.932.723.458 (5)137
Symmetry codes: (i) x+1/2, −y+1/2, z; (ii) x−1/2, −y−1/2, z; (iii) x, y+1, z.
Acknowledgements top

The authors thank the Thailand Research Fund (TRF) for research grant (RSA 5280033) and Prince of Songkla University for financial support through the Crystal Materials Research Unit. The authors also thank Universiti Sains Malaysia for a Research University Golden Goose grant No. 1001/PFIZIK/811012.

references
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