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Acta Cryst. (2011). E67, o1813    [ doi:10.1107/S160053681102407X ]

3-Hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)(thiophen-3-yl)methyl]-5,5-dimethylcyclohex-2-en-1-one

M. Asad, C.-W. Oo, H. Osman, M. M. Rosli and H.-K. Fun

Abstract top

The asymmetric unit of the title compound, C21H26O4S, consists of two independent molecules. In both molecules, intramolecular O-H...O hydrogen bonds stabilize the molecular structure. In the crystal, each molecule and its symmetry-related molecule by twofold rotation form a dimer through a pair of intermolecular C-H...O hydrogen bonds. In one of the molecules, the thiophene group is disordered over two sets of sites with occupancies of 0.735 (3) and 0.265 (3).

Comment top

We reported here the crystal structure of a bis compound which was synthesized from thiophene-3-carboxaldehyde and an active methylene compound, 5,5-dimethylcyclohexan-1,3-dione (dimedone) by using well-known Knoevenagel condensation reaction. This reaction was generally used in organic synthesis for C-C bond formation (Tietze & Beifuss, 1991) and active methylene compounds like dimedone was used as a precursor for many heterocyclic compounds (Suh et al., 2000; Choudhary et al., 2006).

There are two independent molecules in the the asymmetric unit (Fig. 1) and all parameters are within normal ranges. In one of the molecules, the thiophene group was disordered over two positions with refined site occupancies of 0.735 (3):0.265 (3). In both molecules, intramolecular hydrogen bonds O3A/B—H1A/B3···O1A/B and O2A/B—H1A/B2···O4A/B (Table 1) help to stabilize the molecular structure. In the crystal structure, the two sets of molecules are interconnected by two intermolecular C10A—H10A···O1Ai and C16B—H16D···O4Bii hydrogen bonds to form dimers (Fig. 2).

Related literature top

For general background to the title compound, see: Tietze & Beifuss (1991); Suh et al. (2000); Choudhary et al. (2006). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of thiophene-3-carboxaldehyde (4.46 mmol, 0.5 g) and dimedone (8.92 mmol, 1.25 g) in 20 ml of methanol was stirred overnight at room temperature. The completion of the reaction was monitored by TLC. After the reaction was completed, the crude product was separated, filtered, washed with methanol and dried. The isolated product was further purified by recrystallization from chloroform-methanol (1:1 v/v) to give the pure title compound in 85% yield.

Refinement top

One of the thiophene group was disordered over two positions with refined site occupancies of 0.735 (3):0.265 (3). The same Uij parameters were applied to the C1B/C1Y and C3B/C3Y. Distance and rigid body restraint were used on disorder part of the molecular structure. O-bound H atoms were located from the difference map and refined freely. The rest of H atom were positioned geometrically with C—H = 0.95–1.00 Å and refined using a riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).

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 molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius. Dashed lines indicate the O—H···O hydrogen bonds.
[Figure 2] Fig. 2. A packing diagram of the title compound, viewed along the c axis. Dashed lines indicate hydrogen bonds. Minor components and H atoms not involved in the hydrogen bonds have been omitted for clarity.
3-hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)(thiophen- 3-yl)methyl]-5,5-dimethylcyclohex-2-en-1-one top
Crystal data top
C21H26O4SDx = 1.298 Mg m−3
Mr = 374.48Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/aCell parameters from 9719 reflections
Hall symbol: -I 4adθ = 2.2–29.9°
a = 20.3770 (1) ŵ = 0.19 mm−1
c = 36.9066 (7) ÅT = 100 K
V = 15324.4 (3) Å3Block, colourless
Z = 320.38 × 0.28 × 0.24 mm
F(000) = 6400
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		11335 independent reflections
Radiation source: fine-focus sealed tube9435 reflections with I > 2σ(I)
graphiteRint = 0.053
φ and ω scansθmax = 30.2°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −28→28
Tmin = 0.930, Tmax = 0.955k = −28→28
162998 measured reflectionsl = −52→51
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0603P)2 + 23.1894P]
where P = (Fo2 + 2Fc2)/3
11335 reflections(Δ/σ)max = 0.001
518 parametersΔρmax = 0.85 e Å−3
86 restraintsΔρmin = −0.81 e Å−3
Crystal data top
C21H26O4SZ = 32
Mr = 374.48Mo Kα radiation
Tetragonal, I41/aµ = 0.19 mm−1
a = 20.3770 (1) ÅT = 100 K
c = 36.9066 (7) Å0.38 × 0.28 × 0.24 mm
V = 15324.4 (3) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		11335 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		9435 reflections with I > 2σ(I)
Tmin = 0.930, Tmax = 0.955Rint = 0.053
162998 measured reflectionsθmax = 30.2°
Refinement top
R[F2 > 2σ(F2)] = 0.049 w = 1/[σ2(Fo2) + (0.0603P)2 + 23.1894P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.132Δρmax = 0.85 e Å−3
S = 1.05Δρmin = −0.81 e Å−3
11335 reflectionsAbsolute structure: ?
518 parametersFlack parameter: ?
86 restraintsRogers parameter: ?
H atoms treated by a mixture of independent and constrained refinement
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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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*/UeqOcc. (<1)
S1A0.26498 (2)0.53295 (2)0.064534 (12)0.02667 (10)
O1A0.43198 (5)0.66891 (5)0.06947 (3)0.01577 (19)
O2A0.32661 (5)0.79671 (5)−0.01962 (3)0.0185 (2)
O3A0.48148 (5)0.58783 (5)0.02392 (3)0.0160 (2)
O4A0.38506 (5)0.71916 (5)−0.06694 (3)0.0177 (2)
C1A0.29441 (7)0.60778 (7)0.05155 (4)0.0174 (3)
H1AA0.28490.64760.06390.021*
C2A0.30093 (7)0.49167 (6)0.03039 (4)0.0136 (2)
H2AA0.29760.44580.02610.016*
C3A0.33798 (7)0.53824 (7)0.00845 (4)0.0184 (3)
H3AA0.36270.5260−0.01230.022*
C4A0.33333 (6)0.60401 (7)0.02128 (4)0.0140 (2)
C5A0.36197 (6)0.66325 (6)0.00161 (3)0.0126 (2)
H5AA0.32780.6755−0.01660.015*
C6A0.36899 (6)0.72403 (6)0.02540 (4)0.0126 (2)
C7A0.34849 (7)0.78460 (7)0.01386 (4)0.0143 (2)
C8A0.34971 (7)0.84505 (7)0.03702 (4)0.0168 (3)
H8AA0.30920.87060.03240.020*
H8AB0.38750.87250.02960.020*
C9A0.35486 (7)0.83136 (7)0.07775 (4)0.0139 (2)
C10A0.40850 (7)0.77994 (7)0.08357 (4)0.0154 (3)
H10A0.45170.80090.07940.018*
H10B0.40720.76550.10920.018*
C11A0.40332 (6)0.72029 (7)0.05960 (4)0.0129 (2)
C12A0.42293 (6)0.64826 (6)−0.02089 (4)0.0127 (2)
C13A0.47480 (7)0.61050 (6)−0.00969 (4)0.0133 (2)
C14A0.53007 (7)0.59015 (7)−0.03387 (4)0.0156 (3)
H14A0.54140.5439−0.02850.019*
H14B0.56900.6173−0.02810.019*
C15A0.51536 (7)0.59647 (7)−0.07442 (4)0.0142 (2)
C16A0.48509 (7)0.66420 (7)−0.08030 (4)0.0158 (3)
H16A0.51920.6979−0.07600.019*
H16B0.47100.6679−0.10590.019*
C17A0.42705 (7)0.67870 (7)−0.05621 (4)0.0141 (2)
C18A0.57947 (7)0.59155 (7)−0.09582 (4)0.0187 (3)
H18A0.60930.6266−0.08820.028*
H18B0.57020.5960−0.12180.028*
H18C0.60000.5489−0.09120.028*
C19A0.46737 (7)0.54295 (7)−0.08661 (4)0.0192 (3)
H19A0.42580.5480−0.07360.029*
H19B0.48610.4997−0.08130.029*
H19C0.45950.5470−0.11270.029*
C20A0.28941 (7)0.80673 (8)0.09259 (4)0.0198 (3)
H20A0.27750.76560.08050.030*
H20B0.25530.83970.08810.030*
H20C0.29340.79910.11870.030*
C21A0.37389 (8)0.89450 (7)0.09753 (4)0.0215 (3)
H21A0.37570.88620.12370.032*
H21B0.34120.92860.09250.032*
H21C0.41700.90930.08910.032*
C4B0.81079 (7)0.38819 (7)0.03626 (4)0.0176 (3)
C1B0.8193 (3)0.4552 (2)0.03293 (13)0.0218 (9)0.735 (3)
H1BA0.84430.47580.01440.026*0.735 (3)
S1B0.77821 (9)0.49656 (7)0.06707 (4)0.0299 (3)0.735 (3)
C2B0.7426 (5)0.4251 (5)0.0842 (3)0.0313 (18)0.735 (3)
H2BA0.71170.42290.10340.038*0.735 (3)
C3B0.7670 (7)0.3731 (3)0.0652 (3)0.0218 (8)0.735 (3)
H3BA0.75530.32920.07100.026*0.735 (3)
C1Y0.7673 (19)0.3684 (9)0.0634 (10)0.0218 (9)0.265 (3)
H1YA0.75420.32460.06830.026*0.265 (3)
S1Y0.7417 (4)0.4372 (4)0.0863 (2)0.0358 (12)0.265 (3)
C2Y0.7818 (10)0.4925 (8)0.0583 (4)0.037 (4)0.265 (3)
H2YA0.77630.53880.05740.044*0.265 (3)
C3Y0.8224 (9)0.4555 (8)0.0380 (5)0.0218 (8)0.265 (3)
H3YA0.85810.47470.02530.026*0.265 (3)
O1B0.84132 (5)0.30773 (6)−0.06499 (3)0.0207 (2)
O2B0.96238 (5)0.40881 (5)0.02813 (3)0.0183 (2)
O3B0.81736 (6)0.20770 (6)−0.02075 (3)0.0217 (2)
O4B0.91887 (5)0.32452 (5)0.07410 (3)0.0181 (2)
C5B0.83837 (7)0.33758 (7)0.00993 (4)0.0146 (2)
H5BA0.80030.3258−0.00590.018*
C6B0.88949 (7)0.36484 (7)−0.01621 (4)0.0148 (2)
C7B0.94425 (7)0.39922 (7)−0.00606 (4)0.0149 (2)
C8B0.98958 (7)0.43230 (7)−0.03252 (4)0.0179 (3)
H8BA1.03450.4324−0.02230.021*
H8BB0.97570.4786−0.03540.021*
C9B0.99160 (7)0.39999 (7)−0.06994 (4)0.0180 (3)
C10B0.92029 (8)0.38833 (8)−0.08188 (4)0.0207 (3)
H10C0.89890.4313−0.08610.025*
H10D0.92030.3640−0.10510.025*
C11B0.88085 (7)0.35024 (7)−0.05431 (4)0.0168 (3)
C12B0.85772 (7)0.27305 (7)0.02810 (4)0.0147 (2)
C13B0.84358 (7)0.21397 (7)0.01210 (4)0.0168 (3)
C14B0.85774 (8)0.14916 (7)0.02953 (4)0.0211 (3)
H14C0.89910.13160.01930.025*
H14D0.82210.11810.02320.025*
C15B0.86403 (7)0.15195 (7)0.07086 (4)0.0181 (3)
C16B0.90965 (7)0.20923 (7)0.08039 (4)0.0192 (3)
H16C0.90720.21690.10680.023*
H16D0.95530.19620.07470.023*
C17B0.89507 (7)0.27293 (7)0.06126 (4)0.0150 (2)
C18B0.89383 (9)0.08794 (8)0.08484 (5)0.0261 (3)
H18D0.89930.09060.11120.039*
H18E0.93670.08090.07340.039*
H18F0.86460.05130.07890.039*
C19B0.79651 (8)0.16165 (8)0.08853 (5)0.0246 (3)
H19D0.80140.16230.11490.037*
H19E0.76740.12550.08160.037*
H19F0.77760.20330.08040.037*
C20B1.02941 (9)0.33507 (8)−0.06795 (5)0.0274 (3)
H20D1.07540.3439−0.06180.041*
H20E1.02720.3128−0.09150.041*
H20F1.00990.3070−0.04930.041*
C21B1.02532 (9)0.44528 (8)−0.09711 (4)0.0243 (3)
H21D1.07030.4541−0.08910.036*
H21E1.00100.4867−0.09880.036*
H21F1.02630.4241−0.12100.036*
H1A30.4580 (12)0.6109 (13)0.0393 (7)0.047 (7)*
H1B20.9381 (13)0.3845 (13)0.0434 (7)0.048 (7)*
H1B30.8215 (12)0.2413 (13)−0.0329 (7)0.044 (7)*
H1A20.3405 (12)0.7665 (13)−0.0342 (7)0.046 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0251 (2)0.0266 (2)0.0283 (2)−0.00512 (15)0.00349 (15)0.00306 (15)
O1A0.0161 (5)0.0160 (5)0.0152 (5)0.0019 (4)−0.0022 (4)0.0011 (4)
O2A0.0244 (5)0.0190 (5)0.0120 (5)0.0062 (4)−0.0003 (4)0.0023 (4)
O3A0.0176 (5)0.0181 (5)0.0123 (4)0.0031 (4)−0.0013 (4)0.0014 (4)
O4A0.0201 (5)0.0188 (5)0.0141 (5)0.0038 (4)−0.0010 (4)0.0022 (4)
C1A0.0171 (6)0.0165 (6)0.0186 (6)−0.0024 (5)0.0017 (5)0.0015 (5)
C2A0.0150 (6)0.0094 (5)0.0165 (6)0.0033 (4)−0.0049 (5)−0.0030 (4)
C3A0.0180 (6)0.0172 (6)0.0199 (7)−0.0029 (5)0.0010 (5)−0.0010 (5)
C4A0.0118 (6)0.0152 (6)0.0150 (6)−0.0012 (5)−0.0022 (5)0.0015 (5)
C5A0.0121 (6)0.0137 (6)0.0121 (6)0.0000 (4)−0.0018 (4)0.0009 (4)
C6A0.0119 (6)0.0137 (6)0.0122 (6)−0.0002 (4)0.0004 (4)0.0010 (4)
C7A0.0140 (6)0.0168 (6)0.0121 (6)0.0009 (5)0.0016 (5)0.0015 (5)
C8A0.0218 (7)0.0138 (6)0.0148 (6)0.0019 (5)0.0035 (5)0.0018 (5)
C9A0.0146 (6)0.0135 (6)0.0137 (6)−0.0001 (5)0.0022 (5)0.0005 (5)
C10A0.0143 (6)0.0152 (6)0.0166 (6)−0.0002 (5)−0.0013 (5)−0.0019 (5)
C11A0.0108 (5)0.0147 (6)0.0133 (6)−0.0012 (4)0.0010 (4)0.0009 (5)
C12A0.0134 (6)0.0123 (6)0.0124 (6)−0.0008 (4)−0.0009 (4)−0.0005 (4)
C13A0.0157 (6)0.0120 (6)0.0123 (6)−0.0014 (5)−0.0011 (5)−0.0005 (4)
C14A0.0149 (6)0.0164 (6)0.0154 (6)0.0026 (5)−0.0005 (5)−0.0013 (5)
C15A0.0157 (6)0.0126 (6)0.0144 (6)−0.0008 (5)0.0006 (5)−0.0017 (5)
C16A0.0186 (6)0.0148 (6)0.0140 (6)0.0003 (5)0.0018 (5)0.0013 (5)
C17A0.0162 (6)0.0137 (6)0.0124 (6)−0.0013 (5)−0.0012 (5)−0.0014 (5)
C18A0.0190 (7)0.0182 (7)0.0188 (7)−0.0007 (5)0.0039 (5)−0.0033 (5)
C19A0.0205 (7)0.0173 (6)0.0198 (7)−0.0038 (5)0.0012 (5)−0.0055 (5)
C20A0.0171 (6)0.0236 (7)0.0189 (7)−0.0009 (5)0.0060 (5)0.0012 (5)
C21A0.0269 (8)0.0159 (6)0.0216 (7)0.0000 (6)−0.0003 (6)−0.0039 (5)
C4B0.0150 (6)0.0233 (7)0.0145 (6)0.0062 (5)−0.0038 (5)−0.0030 (5)
C1B0.0236 (13)0.0194 (11)0.022 (2)0.0077 (10)−0.0049 (14)−0.0066 (12)
S1B0.0293 (4)0.0286 (4)0.0317 (8)0.0114 (3)−0.0019 (5)−0.0124 (4)
C2B0.027 (3)0.042 (4)0.025 (3)−0.002 (3)−0.0004 (17)0.005 (3)
C3B0.0186 (11)0.032 (2)0.0153 (17)0.0046 (17)0.0008 (11)−0.0021 (15)
C1Y0.0236 (13)0.0194 (11)0.022 (2)0.0077 (10)−0.0049 (14)−0.0066 (12)
S1Y0.0376 (19)0.045 (3)0.0253 (14)0.0207 (17)−0.0076 (11)−0.0104 (14)
C2Y0.041 (6)0.051 (6)0.018 (6)0.015 (5)−0.015 (4)−0.005 (4)
C3Y0.0186 (11)0.032 (2)0.0153 (17)0.0046 (17)0.0008 (11)−0.0021 (15)
O1B0.0212 (5)0.0246 (5)0.0163 (5)−0.0045 (4)−0.0028 (4)−0.0036 (4)
O2B0.0219 (5)0.0187 (5)0.0143 (5)−0.0043 (4)−0.0039 (4)0.0000 (4)
O3B0.0253 (6)0.0230 (6)0.0167 (5)−0.0058 (4)−0.0008 (4)−0.0039 (4)
O4B0.0190 (5)0.0184 (5)0.0169 (5)−0.0016 (4)−0.0034 (4)−0.0001 (4)
C5B0.0134 (6)0.0172 (6)0.0132 (6)0.0015 (5)−0.0022 (5)−0.0021 (5)
C6B0.0164 (6)0.0150 (6)0.0130 (6)0.0012 (5)−0.0012 (5)−0.0006 (5)
C7B0.0189 (6)0.0118 (6)0.0140 (6)0.0018 (5)−0.0021 (5)−0.0006 (5)
C8B0.0213 (7)0.0149 (6)0.0175 (6)−0.0039 (5)−0.0008 (5)0.0017 (5)
C9B0.0211 (7)0.0136 (6)0.0193 (7)−0.0006 (5)0.0033 (5)0.0000 (5)
C10B0.0254 (7)0.0223 (7)0.0143 (6)−0.0026 (6)0.0005 (5)−0.0011 (5)
C11B0.0174 (6)0.0179 (6)0.0152 (6)0.0008 (5)−0.0011 (5)−0.0018 (5)
C12B0.0132 (6)0.0164 (6)0.0144 (6)0.0003 (5)0.0011 (5)−0.0009 (5)
C13B0.0144 (6)0.0198 (7)0.0163 (6)−0.0025 (5)0.0030 (5)−0.0020 (5)
C14B0.0263 (7)0.0159 (6)0.0211 (7)−0.0021 (5)0.0053 (6)−0.0022 (5)
C15B0.0180 (6)0.0163 (6)0.0200 (7)−0.0006 (5)0.0056 (5)0.0005 (5)
C16B0.0184 (7)0.0186 (7)0.0208 (7)0.0002 (5)−0.0011 (5)0.0039 (5)
C17B0.0124 (6)0.0174 (6)0.0152 (6)0.0012 (5)0.0014 (5)0.0004 (5)
C18B0.0305 (8)0.0188 (7)0.0289 (8)0.0031 (6)0.0073 (7)0.0054 (6)
C19B0.0214 (7)0.0266 (8)0.0257 (8)0.0002 (6)0.0088 (6)0.0014 (6)
C20B0.0284 (8)0.0173 (7)0.0364 (9)0.0032 (6)0.0103 (7)0.0020 (6)
C21B0.0308 (8)0.0209 (7)0.0212 (7)−0.0041 (6)0.0063 (6)0.0020 (6)
Geometric parameters (Å, °) top
S1A—C2A1.6829 (14)C4B—C5B1.5244 (19)
S1A—C1A1.7071 (15)C1B—S1B1.732 (6)
O1A—C11A1.2530 (16)C1B—H1BA0.9500
O2A—C7A1.3368 (16)S1B—C2B1.745 (9)
O2A—H1A20.87 (3)C2B—C3B1.364 (11)
O3A—C13A1.3308 (16)C2B—H2BA0.9500
O3A—H1A30.88 (3)C3B—H3BA0.9500
O4A—C17A1.2524 (17)C1Y—S1Y1.718 (19)
C1A—C4A1.3722 (19)C1Y—H1YA0.9500
C1A—H1AA0.9500S1Y—C2Y1.734 (14)
C2A—C3A1.458 (2)C2Y—C3Y1.346 (19)
C2A—H2AA0.9500C2Y—H2YA0.9500
C3A—C4A1.4246 (19)C3Y—H3YA0.9500
C3A—H3AA0.9500O1B—C11B1.2467 (18)
C4A—C5A1.5249 (18)O2B—C7B1.3291 (16)
C5A—C6A1.5247 (18)O2B—H1B20.90 (3)
C5A—C12A1.5252 (18)O3B—C13B1.3309 (18)
C5A—H5AA1.0000O3B—H1B30.82 (3)
C6A—C7A1.3708 (18)O4B—C17B1.2510 (17)
C6A—C11A1.4452 (18)C5B—C6B1.5245 (19)
C7A—C8A1.4995 (19)C5B—C12B1.5278 (19)
C8A—C9A1.5323 (19)C5B—H5BA1.0000
C8A—H8AA0.9900C6B—C7B1.3699 (19)
C8A—H8AB0.9900C6B—C11B1.4481 (19)
C9A—C20A1.5265 (19)C7B—C8B1.504 (2)
C9A—C21A1.5293 (19)C8B—C9B1.531 (2)
C9A—C10A1.5293 (19)C8B—H8BA0.9900
C10A—C11A1.5069 (19)C8B—H8BB0.9900
C10A—H10A0.9900C9B—C21B1.526 (2)
C10A—H10B0.9900C9B—C20B1.533 (2)
C12A—C13A1.3711 (18)C9B—C10B1.537 (2)
C12A—C17A1.4459 (18)C10B—C11B1.511 (2)
C13A—C14A1.4956 (19)C10B—H10C0.9900
C14A—C15A1.5317 (19)C10B—H10D0.9900
C14A—H14A0.9900C12B—C13B1.3715 (19)
C14A—H14B0.9900C12B—C17B1.4414 (19)
C15A—C16A1.5272 (19)C13B—C14B1.497 (2)
C15A—C18A1.5298 (19)C14B—C15B1.532 (2)
C15A—C19A1.5324 (19)C14B—H14C0.9900
C16A—C17A1.5087 (19)C14B—H14D0.9900
C16A—H16A0.9900C15B—C18B1.528 (2)
C16A—H16B0.9900C15B—C16B1.533 (2)
C18A—H18A0.9800C15B—C19B1.535 (2)
C18A—H18B0.9800C16B—C17B1.507 (2)
C18A—H18C0.9800C16B—H16C0.9900
C19A—H19A0.9800C16B—H16D0.9900
C19A—H19B0.9800C18B—H18D0.9800
C19A—H19C0.9800C18B—H18E0.9800
C20A—H20A0.9800C18B—H18F0.9800
C20A—H20B0.9800C19B—H19D0.9800
C20A—H20C0.9800C19B—H19E0.9800
C21A—H21A0.9800C19B—H19F0.9800
C21A—H21B0.9800C20B—H20D0.9800
C21A—H21C0.9800C20B—H20E0.9800
C4B—C1B1.382 (5)C20B—H20F0.9800
C4B—C3Y1.393 (16)C21B—H21D0.9800
C4B—C1Y1.396 (18)C21B—H21E0.9800
C4B—C3B1.426 (6)C21B—H21F0.9800
C2A—S1A—C1A94.78 (7)C4B—C1B—S1B110.8 (3)
C7A—O2A—H1A2109.6 (17)C4B—C1B—H1BA124.6
C13A—O3A—H1A3111.2 (17)S1B—C1B—H1BA124.6
C4A—C1A—S1A112.43 (11)C1B—S1B—C2B93.4 (4)
C4A—C1A—H1AA123.8C3B—C2B—S1B108.1 (6)
S1A—C1A—H1AA123.8C3B—C2B—H2BA125.9
C3A—C2A—S1A108.42 (10)S1B—C2B—H2BA125.9
C3A—C2A—H2AA125.8C2B—C3B—C4B116.4 (6)
S1A—C2A—H2AA125.8C2B—C3B—H3BA121.8
C4A—C3A—C2A113.14 (12)C4B—C3B—H3BA121.8
C4A—C3A—H3AA123.4C4B—C1Y—S1Y108.1 (11)
C2A—C3A—H3AA123.4C4B—C1Y—H1YA126.0
C1A—C4A—C3A111.21 (12)S1Y—C1Y—H1YA126.0
C1A—C4A—C5A124.37 (12)C1Y—S1Y—C2Y95.3 (9)
C3A—C4A—C5A124.13 (12)C3Y—C2Y—S1Y104.9 (12)
C6A—C5A—C4A113.88 (11)C3Y—C2Y—H2YA127.5
C6A—C5A—C12A113.57 (11)S1Y—C2Y—H2YA127.5
C4A—C5A—C12A114.35 (11)C2Y—C3Y—C4B118.2 (14)
C6A—C5A—H5AA104.5C2Y—C3Y—H3YA120.9
C4A—C5A—H5AA104.5C4B—C3Y—H3YA120.9
C12A—C5A—H5AA104.5C7B—O2B—H1B2111.2 (16)
C7A—C6A—C11A117.78 (12)C13B—O3B—H1B3112.0 (18)
C7A—C6A—C5A121.60 (12)C4B—C5B—C6B114.13 (12)
C11A—C6A—C5A120.37 (11)C4B—C5B—C12B113.43 (11)
O2A—C7A—C6A123.70 (13)C6B—C5B—C12B114.51 (11)
O2A—C7A—C8A112.39 (12)C4B—C5B—H5BA104.4
C6A—C7A—C8A123.89 (12)C6B—C5B—H5BA104.4
C7A—C8A—C9A114.25 (11)C12B—C5B—H5BA104.4
C7A—C8A—H8AA108.7C7B—C6B—C11B118.01 (13)
C9A—C8A—H8AA108.7C7B—C6B—C5B124.75 (12)
C7A—C8A—H8AB108.7C11B—C6B—C5B117.17 (12)
C9A—C8A—H8AB108.7O2B—C7B—C6B124.14 (13)
H8AA—C8A—H8AB107.6O2B—C7B—C8B112.32 (12)
C20A—C9A—C21A109.09 (12)C6B—C7B—C8B123.51 (12)
C20A—C9A—C10A110.41 (11)C7B—C8B—C9B114.18 (12)
C21A—C9A—C10A109.16 (12)C7B—C8B—H8BA108.7
C20A—C9A—C8A110.60 (12)C9B—C8B—H8BA108.7
C21A—C9A—C8A109.41 (11)C7B—C8B—H8BB108.7
C10A—C9A—C8A108.13 (11)C9B—C8B—H8BB108.7
C11A—C10A—C9A114.85 (11)H8BA—C8B—H8BB107.6
C11A—C10A—H10A108.6C21B—C9B—C8B110.18 (12)
C9A—C10A—H10A108.6C21B—C9B—C20B109.09 (13)
C11A—C10A—H10B108.6C8B—C9B—C20B109.97 (13)
C9A—C10A—H10B108.6C21B—C9B—C10B109.31 (13)
H10A—C10A—H10B107.5C8B—C9B—C10B107.45 (12)
O1A—C11A—C6A121.57 (12)C20B—C9B—C10B110.83 (13)
O1A—C11A—C10A118.08 (12)C11B—C10B—C9B112.90 (12)
C6A—C11A—C10A120.27 (12)C11B—C10B—H10C109.0
C13A—C12A—C17A117.89 (12)C9B—C10B—H10C109.0
C13A—C12A—C5A125.17 (12)C11B—C10B—H10D109.0
C17A—C12A—C5A116.88 (11)C9B—C10B—H10D109.0
O3A—C13A—C12A123.70 (12)H10C—C10B—H10D107.8
O3A—C13A—C14A112.51 (12)O1B—C11B—C6B121.90 (13)
C12A—C13A—C14A123.79 (12)O1B—C11B—C10B119.18 (13)
C13A—C14A—C15A114.35 (11)C6B—C11B—C10B118.92 (12)
C13A—C14A—H14A108.7C13B—C12B—C17B118.36 (13)
C15A—C14A—H14A108.7C13B—C12B—C5B120.82 (12)
C13A—C14A—H14B108.7C17B—C12B—C5B120.69 (12)
C15A—C14A—H14B108.7O3B—C13B—C12B124.10 (14)
H14A—C14A—H14B107.6O3B—C13B—C14B112.59 (13)
C16A—C15A—C18A109.32 (11)C12B—C13B—C14B123.29 (13)
C16A—C15A—C14A107.09 (11)C13B—C14B—C15B114.29 (12)
C18A—C15A—C14A109.38 (11)C13B—C14B—H14C108.7
C16A—C15A—C19A110.11 (12)C15B—C14B—H14C108.7
C18A—C15A—C19A110.28 (11)C13B—C14B—H14D108.7
C14A—C15A—C19A110.60 (12)C15B—C14B—H14D108.7
C17A—C16A—C15A114.20 (11)H14C—C14B—H14D107.6
C17A—C16A—H16A108.7C18B—C15B—C14B109.73 (13)
C15A—C16A—H16A108.7C18B—C15B—C16B109.35 (13)
C17A—C16A—H16B108.7C14B—C15B—C16B107.90 (12)
C15A—C16A—H16B108.7C18B—C15B—C19B108.82 (12)
H16A—C16A—H16B107.6C14B—C15B—C19B110.66 (13)
O4A—C17A—C12A121.85 (12)C16B—C15B—C19B110.36 (12)
O4A—C17A—C16A118.57 (12)C17B—C16B—C15B115.39 (12)
C12A—C17A—C16A119.51 (12)C17B—C16B—H16C108.4
C15A—C18A—H18A109.5C15B—C16B—H16C108.4
C15A—C18A—H18B109.5C17B—C16B—H16D108.4
H18A—C18A—H18B109.5C15B—C16B—H16D108.4
C15A—C18A—H18C109.5H16C—C16B—H16D107.5
H18A—C18A—H18C109.5O4B—C17B—C12B121.67 (13)
H18B—C18A—H18C109.5O4B—C17B—C16B118.02 (12)
C15A—C19A—H19A109.5C12B—C17B—C16B120.22 (12)
C15A—C19A—H19B109.5C15B—C18B—H18D109.5
H19A—C19A—H19B109.5C15B—C18B—H18E109.5
C15A—C19A—H19C109.5H18D—C18B—H18E109.5
H19A—C19A—H19C109.5C15B—C18B—H18F109.5
H19B—C19A—H19C109.5H18D—C18B—H18F109.5
C9A—C20A—H20A109.5H18E—C18B—H18F109.5
C9A—C20A—H20B109.5C15B—C19B—H19D109.5
H20A—C20A—H20B109.5C15B—C19B—H19E109.5
C9A—C20A—H20C109.5H19D—C19B—H19E109.5
H20A—C20A—H20C109.5C15B—C19B—H19F109.5
H20B—C20A—H20C109.5H19D—C19B—H19F109.5
C9A—C21A—H21A109.5H19E—C19B—H19F109.5
C9A—C21A—H21B109.5C9B—C20B—H20D109.5
H21A—C21A—H21B109.5C9B—C20B—H20E109.5
C9A—C21A—H21C109.5H20D—C20B—H20E109.5
H21A—C21A—H21C109.5C9B—C20B—H20F109.5
H21B—C21A—H21C109.5H20D—C20B—H20F109.5
C1B—C4B—C1Y115.4 (9)H20E—C20B—H20F109.5
C3Y—C4B—C1Y111.0 (8)C9B—C21B—H21D109.5
C1B—C4B—C3B111.0 (3)C9B—C21B—H21E109.5
C3Y—C4B—C3B106.5 (9)H21D—C21B—H21E109.5
C1B—C4B—C5B124.4 (3)C9B—C21B—H21F109.5
C3Y—C4B—C5B129.2 (7)H21D—C21B—H21F109.5
C1Y—C4B—C5B119.7 (8)H21E—C21B—H21F109.5
C3B—C4B—C5B124.2 (3)
C2A—S1A—C1A—C4A−1.00 (12)C5B—C4B—C3B—C2B−174.5 (9)
C1A—S1A—C2A—C3A0.84 (11)C1B—C4B—C1Y—S1Y−4(4)
S1A—C2A—C3A—C4A−0.53 (15)C3Y—C4B—C1Y—S1Y4(3)
S1A—C1A—C4A—C3A0.82 (16)C3B—C4B—C1Y—S1Y14 (32)
S1A—C1A—C4A—C5A174.82 (10)C5B—C4B—C1Y—S1Y−176.2 (13)
C2A—C3A—C4A—C1A−0.19 (17)C4B—C1Y—S1Y—C2Y5(3)
C2A—C3A—C4A—C5A−174.20 (12)C1Y—S1Y—C2Y—C3Y−12 (3)
C1A—C4A—C5A—C6A24.20 (18)S1Y—C2Y—C3Y—C4B17 (2)
C3A—C4A—C5A—C6A−162.57 (13)C1B—C4B—C3Y—C2Y109 (7)
C1A—C4A—C5A—C12A157.06 (13)C1Y—C4B—C3Y—C2Y−15 (2)
C3A—C4A—C5A—C12A−29.70 (18)C3B—C4B—C3Y—C2Y−15 (2)
C4A—C5A—C6A—C7A−133.08 (13)C5B—C4B—C3Y—C2Y165.4 (12)
C12A—C5A—C6A—C7A93.68 (15)C1B—C4B—C5B—C6B13.1 (3)
C4A—C5A—C6A—C11A52.79 (16)C3Y—C4B—C5B—C6B4.8 (10)
C12A—C5A—C6A—C11A−80.45 (15)C1Y—C4B—C5B—C6B−175 (2)
C11A—C6A—C7A—O2A168.04 (12)C3B—C4B—C5B—C6B−174.1 (8)
C5A—C6A—C7A—O2A−6.2 (2)C1B—C4B—C5B—C12B146.7 (3)
C11A—C6A—C7A—C8A−10.3 (2)C3Y—C4B—C5B—C12B138.4 (10)
C5A—C6A—C7A—C8A175.43 (12)C1Y—C4B—C5B—C12B−42 (2)
O2A—C7A—C8A—C9A163.14 (12)C3B—C4B—C5B—C12B−40.5 (9)
C6A—C7A—C8A—C9A−18.4 (2)C4B—C5B—C6B—C7B52.84 (18)
C7A—C8A—C9A—C20A−74.73 (15)C12B—C5B—C6B—C7B−80.25 (17)
C7A—C8A—C9A—C21A165.07 (12)C4B—C5B—C6B—C11B−130.44 (13)
C7A—C8A—C9A—C10A46.28 (16)C12B—C5B—C6B—C11B96.47 (15)
C20A—C9A—C10A—C11A72.02 (15)C11B—C6B—C7B—O2B−171.28 (13)
C21A—C9A—C10A—C11A−168.06 (12)C5B—C6B—C7B—O2B5.4 (2)
C8A—C9A—C10A—C11A−49.11 (15)C11B—C6B—C7B—C8B10.8 (2)
C7A—C6A—C11A—O1A−169.28 (12)C5B—C6B—C7B—C8B−172.53 (13)
C5A—C6A—C11A—O1A5.06 (19)O2B—C7B—C8B—C9B153.75 (12)
C7A—C6A—C11A—C10A7.43 (19)C6B—C7B—C8B—C9B−28.1 (2)
C5A—C6A—C11A—C10A−178.22 (12)C7B—C8B—C9B—C21B166.61 (13)
C9A—C10A—C11A—O1A−159.26 (12)C7B—C8B—C9B—C20B−73.10 (16)
C9A—C10A—C11A—C6A23.91 (18)C7B—C8B—C9B—C10B47.61 (16)
C6A—C5A—C12A—C13A88.43 (16)C21B—C9B—C10B—C11B−173.48 (12)
C4A—C5A—C12A—C13A−44.59 (18)C8B—C9B—C10B—C11B−53.92 (16)
C6A—C5A—C12A—C17A−88.90 (14)C20B—C9B—C10B—C11B66.25 (16)
C4A—C5A—C12A—C17A138.08 (12)C7B—C6B—C11B—O1B163.83 (14)
C17A—C12A—C13A—O3A169.83 (12)C5B—C6B—C11B—O1B−13.1 (2)
C5A—C12A—C13A—O3A−7.5 (2)C7B—C6B—C11B—C10B−17.0 (2)
C17A—C12A—C13A—C14A−10.3 (2)C5B—C6B—C11B—C10B166.05 (13)
C5A—C12A—C13A—C14A172.44 (12)C9B—C10B—C11B—O1B−140.33 (14)
O3A—C13A—C14A—C15A162.39 (11)C9B—C10B—C11B—C6B40.48 (18)
C12A—C13A—C14A—C15A−17.53 (19)C4B—C5B—C12B—C13B138.17 (13)
C13A—C14A—C15A—C16A47.25 (15)C6B—C5B—C12B—C13B−88.41 (16)
C13A—C14A—C15A—C18A165.61 (12)C4B—C5B—C12B—C17B−45.95 (17)
C13A—C14A—C15A—C19A−72.74 (15)C6B—C5B—C12B—C17B87.47 (15)
C18A—C15A—C16A—C17A−171.28 (11)C17B—C12B—C13B—O3B−170.66 (13)
C14A—C15A—C16A—C17A−52.88 (15)C5B—C12B—C13B—O3B5.3 (2)
C19A—C15A—C16A—C17A67.43 (15)C17B—C12B—C13B—C14B7.7 (2)
C13A—C12A—C17A—O4A−172.58 (13)C5B—C12B—C13B—C14B−176.31 (13)
C5A—C12A—C17A—O4A4.95 (19)O3B—C13B—C14B—C15B−159.09 (13)
C13A—C12A—C17A—C16A4.36 (19)C12B—C13B—C14B—C15B22.4 (2)
C5A—C12A—C17A—C16A−178.12 (11)C13B—C14B—C15B—C18B−166.86 (13)
C15A—C16A—C17A—O4A−153.95 (12)C13B—C14B—C15B—C16B−47.79 (17)
C15A—C16A—C17A—C12A29.01 (17)C13B—C14B—C15B—C19B73.04 (16)
C3Y—C4B—C1B—S1B−54 (7)C18B—C15B—C16B—C17B166.62 (13)
C1Y—C4B—C1B—S1B6(3)C14B—C15B—C16B—C17B47.31 (17)
C3B—C4B—C1B—S1B4.1 (7)C19B—C15B—C16B—C17B−73.70 (16)
C5B—C4B—C1B—S1B177.77 (17)C13B—C12B—C17B—O4B168.08 (13)
C4B—C1B—S1B—C2B−5.0 (5)C5B—C12B—C17B—O4B−7.9 (2)
C1B—S1B—C2B—C3B4.4 (11)C13B—C12B—C17B—C16B−8.5 (2)
S1B—C2B—C3B—C4B−2.9 (17)C5B—C12B—C17B—C16B175.52 (12)
C1B—C4B—C3B—C2B−0.8 (15)C15B—C16B—C17B—O4B162.45 (13)
C3Y—C4B—C3B—C2B6(2)C15B—C16B—C17B—C12B−20.85 (19)
C1Y—C4B—C3B—C2B−163 (35)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3A—H1A3···O1A0.88 (3)1.71 (3)2.5638 (15)164 (2)
O2B—H1B2···O4B0.90 (3)1.71 (3)2.5719 (15)159 (3)
O3B—H1B3···O1B0.82 (3)1.84 (3)2.6569 (17)170 (3)
O2A—H1A2···O4A0.87 (3)1.79 (3)2.6393 (15)165 (2)
C10A—H10A···O1Ai0.992.483.4530 (18)169
C16B—H16D···O4Bii0.992.603.5688 (18)167
Symmetry codes: (i) −x+1, −y+3/2, z; (ii) −x+2, −y+1/2, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3A—H1A3···O1A0.88 (3)1.71 (3)2.5638 (15)164 (2)
O2B—H1B2···O4B0.90 (3)1.71 (3)2.5719 (15)159 (3)
O3B—H1B3···O1B0.82 (3)1.84 (3)2.6569 (17)170 (3)
O2A—H1A2···O4A0.87 (3)1.79 (3)2.6393 (15)165 (2)
C10A—H10A···O1Ai0.992.483.4530 (18)169
C16B—H16D···O4Bii0.992.603.5688 (18)167
Symmetry codes: (i) −x+1, −y+3/2, z; (ii) −x+2, −y+1/2, z.
Acknowledgements top

The authors are thankful to Universiti Sains Malaysia (USM) for providing the necessary research facilities and RU research funding under grant No. 1001/PKIMIA/811134. MA also thanks USM for the award of a post-doctoral fellowship. HKF thanks USM for the Research University Grant (No. 1001/PFIZIK/811160).

references
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