3-Methyl-5α-cholest-2-ene

Ketuly, K.A.; Hadi, A.H.A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S160053681003117X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2265

https://doi.org/10.1107/S160053681003117X

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3-Methyl-5α-cholest-2-ene

Kamal Aziz Ketuly,^a ‡ A. Hamid A. Hadi,^a Seik Weng Ng ^a and Edward R. T. Tiekink ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 31 July 2010; accepted 4 August 2010; online 11 August 2010)

In the title cholestane derivative, C₂₈H₄₈ [systematic name: (1S,2S,7R,10R,11R,14R,15R)-2,5,10,15-tetramethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,7.0^11,15]heptadec-4-ene], the cyclohexene ring adopts a half-chair conformation. The parent 5α-cholest-2-ene and the equivalent fragment of the title compound are almost superimposable (r.m.s. deviation = 0.033 Å).

Related literature

For background to this study, see: Ketuly & Hadi (2010 ). For the synthesis, see: Barton et al. (1956 ). For a discussion of the structural features of cholestane derivatives, see: Rajnikant et al. (2006 ). For the structure of 5α-cholest-2-ene, see: Kemlo et al. (1979 ). For ring conformational analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₈H₄₈
M_r = 384.66
Monoclinic, C 2
a = 22.216 (3) Å
b = 11.7576 (15) Å
c = 9.6335 (13) Å
β = 106.652 (2)°
V = 2410.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.06 mm⁻¹
T = 100 K
0.35 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.786, T_max = 0.862
11615 measured reflections
2902 independent reflections
2379 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.121
S = 1.02
2902 reflections
253 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ), DIAMOND (Brandenburg, 2006 ) and Qmol (Gans & Shalloway, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681003117X/hb5593sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681003117X/hb5593Isup2.hkl

checkCIF report

Comment top

The title compound, 3-methyl-5α-cholest-2-ene, (I), has been prepared previously (Barton et al., 1956) as a precursor for the synthesis of steroidal boronic acids and boronates (Ketuly et al., 2010). The geometric and structural features for a series of cholestane derivatives has been described (Rajnikant et al., 2006).

In the structure of (I), Fig. 1, the cyclohexene has a half-chair conformation: the ring-puckering parameters are q₂ = 0.387 (3) Å, q₃ = -0.318 (3) Å, QT = 0.501 (3) Å, φ₂ = 149.2 (5) ° (Cremer & Pople, 1975). With the exception of a small difference in orientation of the terminal residues, the structure of (I) is virtually super-imposable upon the structure of the parent 5α-cholest-2-ene structure (Kemlo et al., 1979). The r.m.s. deviation between the two molecules is 0.033 Å (Gans & Shalloway, 2001).

Related literature top

For background to this study, see: Ketuly & Hadi (2010). For the synthesis, see: Barton et al. (1956). For a discussion on the structural features of cholestane derivatives, see: Rajnikant et al. (2006). For the structure of 5α-cholest-2-ene, see: Kemlo et al. (1979). For ring conformational analysis, see: Cremer & Pople (1975).

Experimental top

The synthesis of the title compound is a modified version of the literature procedure (Barton et al., 1956). 5α-cholestan-3-one (3 g, 8 mmol) in dry ether (40 ml) was added to methylmagnesium iodide [prepared by by the gradual addition of methyl iodide (1.2 ml, 20 mmol) in dry ether (15 ml) to magnesium (0.5 g, 21 mmol) in dry ether (10 ml) during 30 min. with continuous stirring and cooling] and the resulting solution was refluxed for 3 h. The reaction mixture was poured on to ice, then a solution of H₂SO₄ (1.52 g) and water (10 ml) added with stirring. The mixture was extracted three times with ether and washed with saturated NaHCO₃, then with water until neutral. Extracts were dried and evaporated, yielding a white crystalline product (2.92 g, 94% of the mixture isomers: 3α-hydroxy-3β-methyl-5α-cholestane and 3β-hydroxy-3α-methyl-5α-cholestane, m.p. 368–373 K. The mixture of these stereoisomeric alchohols (2 g) was dissolved in glacial acetic acid (25 ml) on warming, then perchloric acid (72%, w/w, 10 drops) was added and the solution heated in hot bath (253–263 K) for 30 min. The solvent and excess reagent were evaporated azeotropically. The yellow solid residue was dissolved in ether, washed with NaHCO₃ then with water, until neutral; each washing was back-extracted three times with ether. The extracts were combined; dried and evaporated. A yellow oily residue, which gradually crystallized was recovered (1.81 g, 95%), mp. 342–346 K. This was recrystallized from ether-MeOH, giving (1.739 g, 91%) of the title compound, mp. 348–350 K. This was further recrystallized and colourless blocks of (I) were grown from carbon ethanol:ether (8:1,v/v), m.p. 354–355 K (Lit. Barton et al. (1956) 356–357 K from light petroleum).

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and Qmol (Gans & Shalloway, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. Overlay diagram of (I), shown in blue, with the parent 5α-cholest-2-ene, shown in red.

(1S,2S,7R,10R,11R,14R,15R)- 2,5,10,15-tetramethyl-14-[(2R)-6-methylheptan-2- yl]tetracyclo[8.7.0.0^2,7.0^11,15]heptadec-4-ene top

Crystal data top

C₂₈H₄₈	F(000) = 864
M_r = 384.66	D_x = 1.060 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 1712 reflections
a = 22.216 (3) Å	θ = 2.5–22.9°
b = 11.7576 (15) Å	µ = 0.06 mm⁻¹
c = 9.6335 (13) Å	T = 100 K
β = 106.652 (2)°	Prism, colourless
V = 2410.9 (5) Å³	0.35 × 0.15 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	2902 independent reflections
Radiation source: fine-focus sealed tube	2379 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
ω scan	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→28
T_min = 0.786, T_max = 0.862	k = −15→15
11615 measured reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0616P)² + 0.7202P] where P = (F_o² + 2F_c²)/3
2902 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.24 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₈H₄₈	V = 2410.9 (5) Å³
M_r = 384.66	Z = 4
Monoclinic, C2	Mo Kα radiation
a = 22.216 (3) Å	µ = 0.06 mm⁻¹
b = 11.7576 (15) Å	T = 100 K
c = 9.6335 (13) Å	0.35 × 0.15 × 0.05 mm
β = 106.652 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	2902 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2379 reflections with I > 2σ(I)
T_min = 0.786, T_max = 0.862	R_int = 0.060
11615 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	1 restraint
wR(F²) = 0.121	H-atom parameters constrained
S = 1.02	Δρ_max = 0.24 e Å⁻³
2902 reflections	Δρ_min = −0.20 e Å⁻³
253 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

	x	y	z	U_iso*/U_eq
C1	0.25641 (12)	0.4995 (2)	0.1799 (3)	0.0211 (6)
H1A	0.2370	0.5179	0.0752	0.025*
C2	0.22521 (14)	0.3904 (3)	0.2106 (3)	0.0259 (6)
H2A	0.2276	0.3322	0.1382	0.031*
H2B	0.2488	0.3614	0.3074	0.031*
C3	0.15797 (13)	0.4068 (3)	0.2063 (3)	0.0226 (6)
C4	0.12007 (14)	0.3006 (3)	0.2017 (3)	0.0289 (7)
H4A	0.0771	0.3210	0.2002	0.043*
H4B	0.1392	0.2543	0.2876	0.043*
H4C	0.1191	0.2572	0.1142	0.043*
C5	0.13404 (13)	0.5112 (3)	0.2097 (3)	0.0241 (6)
H5A	0.0909	0.5172	0.2052	0.029*
C6	0.17105 (12)	0.6191 (3)	0.2201 (3)	0.0226 (6)
H6A	0.1598	0.6704	0.2902	0.027*
H6B	0.1588	0.6572	0.1245	0.027*
C7	0.24280 (12)	0.6016 (2)	0.2674 (3)	0.0178 (5)
C8	0.26358 (13)	0.5758 (3)	0.4308 (3)	0.0238 (6)
H8A	0.2421	0.5073	0.4498	0.036*
H8B	0.2527	0.6402	0.4837	0.036*
H8C	0.3091	0.5636	0.4631	0.036*
C9	0.27602 (13)	0.7082 (2)	0.2307 (3)	0.0175 (6)
H9A	0.2565	0.7224	0.1250	0.021*
C10	0.34646 (12)	0.6901 (2)	0.2494 (3)	0.0181 (6)
H10A	0.3679	0.6750	0.3541	0.022*
C11	0.35657 (12)	0.5880 (2)	0.1617 (3)	0.0233 (6)
H11A	0.3387	0.6045	0.0572	0.028*
H11B	0.4022	0.5747	0.1804	0.028*
C12	0.32603 (13)	0.4813 (2)	0.1997 (3)	0.0224 (6)
H12A	0.3316	0.4178	0.1369	0.027*
H12B	0.3470	0.4600	0.3015	0.027*
C13	0.26474 (12)	0.8173 (2)	0.3085 (3)	0.0204 (6)
H13A	0.2189	0.8302	0.2868	0.025*
H13B	0.2819	0.8064	0.4144	0.025*
C14	0.29511 (12)	0.9230 (2)	0.2637 (3)	0.0193 (6)
H14A	0.2748	0.9393	0.1600	0.023*
H14B	0.2883	0.9892	0.3207	0.023*
C15	0.36558 (12)	0.9056 (2)	0.2883 (3)	0.0173 (6)
C16	0.39946 (13)	0.8959 (3)	0.4510 (3)	0.0222 (6)
H16A	0.4446	0.8853	0.4651	0.033*
H16B	0.3828	0.8307	0.4915	0.033*
H16C	0.3926	0.9656	0.5003	0.033*
C17	0.37381 (12)	0.7980 (2)	0.2051 (3)	0.0169 (5)
H17A	0.3499	0.8119	0.1016	0.020*
C18	0.44307 (12)	0.7989 (2)	0.2104 (3)	0.0210 (6)
H18A	0.4504	0.7547	0.1292	0.025*
H18B	0.4696	0.7676	0.3031	0.025*
C19	0.45632 (13)	0.9275 (2)	0.1962 (3)	0.0217 (6)
H19A	0.4954	0.9500	0.2705	0.026*
H19B	0.4614	0.9437	0.0993	0.026*
C20	0.39944 (12)	0.9943 (2)	0.2177 (3)	0.0189 (6)
H20A	0.3708	1.0120	0.1193	0.023*
C21	0.41998 (12)	1.1083 (3)	0.2951 (3)	0.0216 (6)
H21A	0.4519	1.0910	0.3894	0.026*
C22	0.36660 (14)	1.1740 (3)	0.3294 (3)	0.0284 (7)
H22A	0.3830	1.2450	0.3792	0.043*
H22B	0.3485	1.1276	0.3919	0.043*
H22C	0.3341	1.1914	0.2391	0.043*
C23	0.45225 (13)	1.1824 (3)	0.2065 (3)	0.0228 (6)
H23A	0.4762	1.1323	0.1590	0.027*
H23B	0.4194	1.2209	0.1291	0.027*
C24	0.49675 (14)	1.2726 (3)	0.2937 (3)	0.0263 (7)
H24A	0.4731	1.3236	0.3410	0.032*
H24B	0.5301	1.2349	0.3708	0.032*
C25	0.52703 (13)	1.3430 (2)	0.1990 (3)	0.0216 (6)
H25A	0.4936	1.3870	0.1297	0.026*
H25B	0.5452	1.2902	0.1418	0.026*
C26	0.57833 (12)	1.4256 (2)	0.2788 (3)	0.0205 (6)
H26A	0.6114	1.3814	0.3508	0.025*
C27	0.60833 (15)	1.4801 (3)	0.1707 (3)	0.0307 (7)
H27A	0.6407	1.5342	0.2215	0.046*
H27B	0.5761	1.5201	0.0958	0.046*
H27C	0.6274	1.4208	0.1256	0.046*
C28	0.55335 (14)	1.5163 (3)	0.3599 (3)	0.0330 (7)
H28A	0.5876	1.5674	0.4094	0.049*
H28B	0.5359	1.4800	0.4315	0.049*
H28C	0.5204	1.5600	0.2913	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0200 (13)	0.0226 (15)	0.0225 (13)	−0.0045 (12)	0.0088 (10)	−0.0041 (12)
C2	0.0297 (15)	0.0215 (15)	0.0303 (15)	−0.0038 (12)	0.0146 (12)	−0.0040 (12)
C3	0.0224 (14)	0.0284 (16)	0.0189 (13)	−0.0070 (12)	0.0090 (11)	−0.0049 (12)
C4	0.0311 (16)	0.0308 (17)	0.0285 (15)	−0.0091 (14)	0.0144 (12)	−0.0083 (14)
C5	0.0181 (13)	0.0316 (17)	0.0249 (14)	−0.0042 (12)	0.0099 (11)	−0.0009 (13)
C6	0.0202 (13)	0.0249 (15)	0.0259 (14)	−0.0031 (12)	0.0115 (11)	−0.0030 (12)
C7	0.0167 (12)	0.0183 (13)	0.0192 (13)	−0.0028 (11)	0.0065 (10)	0.0008 (11)
C8	0.0279 (14)	0.0253 (16)	0.0203 (13)	−0.0025 (12)	0.0102 (11)	0.0007 (12)
C9	0.0174 (13)	0.0186 (14)	0.0171 (13)	−0.0036 (11)	0.0062 (10)	−0.0018 (10)
C10	0.0159 (13)	0.0204 (14)	0.0179 (13)	−0.0001 (11)	0.0045 (10)	0.0020 (11)
C11	0.0163 (12)	0.0236 (15)	0.0318 (15)	−0.0010 (12)	0.0096 (11)	−0.0028 (12)
C12	0.0206 (14)	0.0178 (14)	0.0302 (15)	0.0008 (11)	0.0094 (11)	−0.0017 (12)
C13	0.0167 (13)	0.0226 (15)	0.0249 (14)	0.0005 (11)	0.0106 (11)	0.0000 (12)
C14	0.0164 (13)	0.0207 (14)	0.0223 (13)	−0.0016 (11)	0.0080 (10)	0.0012 (11)
C15	0.0172 (13)	0.0191 (15)	0.0171 (12)	−0.0005 (11)	0.0070 (10)	0.0026 (11)
C16	0.0241 (14)	0.0261 (15)	0.0175 (12)	−0.0035 (12)	0.0078 (11)	−0.0004 (11)
C17	0.0143 (12)	0.0209 (14)	0.0162 (12)	−0.0014 (11)	0.0056 (9)	−0.0010 (11)
C18	0.0182 (13)	0.0207 (14)	0.0259 (14)	−0.0011 (12)	0.0092 (11)	−0.0012 (12)
C19	0.0199 (14)	0.0230 (14)	0.0246 (14)	−0.0043 (12)	0.0103 (11)	−0.0012 (11)
C20	0.0168 (12)	0.0236 (14)	0.0169 (12)	−0.0023 (12)	0.0060 (10)	0.0046 (11)
C21	0.0207 (13)	0.0253 (15)	0.0200 (13)	−0.0038 (12)	0.0078 (11)	0.0016 (11)
C22	0.0275 (15)	0.0223 (15)	0.0384 (17)	−0.0014 (13)	0.0143 (13)	−0.0020 (13)
C23	0.0249 (15)	0.0220 (15)	0.0223 (14)	−0.0047 (12)	0.0081 (11)	0.0010 (12)
C24	0.0290 (15)	0.0284 (17)	0.0211 (14)	−0.0083 (13)	0.0064 (12)	−0.0009 (12)
C25	0.0241 (14)	0.0214 (15)	0.0194 (13)	−0.0051 (12)	0.0063 (11)	−0.0009 (11)
C26	0.0179 (13)	0.0209 (14)	0.0223 (13)	−0.0025 (12)	0.0054 (10)	0.0000 (11)
C27	0.0324 (16)	0.0277 (16)	0.0344 (16)	−0.0086 (14)	0.0133 (13)	0.0018 (14)
C28	0.0269 (15)	0.0346 (19)	0.0387 (17)	−0.0073 (14)	0.0114 (13)	−0.0130 (15)

Geometric parameters (Å, º) top

C1—C12	1.519 (4)	C15—C16	1.537 (3)
C1—C2	1.528 (4)	C15—C20	1.552 (4)
C1—C7	1.545 (4)	C16—H16A	0.9800
C1—H1A	1.0000	C16—H16B	0.9800
C2—C3	1.495 (4)	C16—H16C	0.9800
C2—H2A	0.9900	C17—C18	1.525 (3)
C2—H2B	0.9900	C17—H17A	1.0000
C3—C5	1.342 (4)	C18—C19	1.554 (4)
C3—C4	1.499 (4)	C18—H18A	0.9900
C4—H4A	0.9800	C18—H18B	0.9900
C4—H4B	0.9800	C19—C20	1.552 (4)
C4—H4C	0.9800	C19—H19A	0.9900
C5—C6	1.499 (4)	C19—H19B	0.9900
C5—H5A	0.9500	C20—C21	1.538 (4)
C6—C7	1.541 (3)	C20—H20A	1.0000
C6—H6A	0.9900	C21—C22	1.529 (4)
C6—H6B	0.9900	C21—C23	1.533 (4)
C7—C8	1.539 (3)	C21—H21A	1.0000
C7—C9	1.546 (4)	C22—H22A	0.9800
C8—H8A	0.9800	C22—H22B	0.9800
C8—H8B	0.9800	C22—H22C	0.9800
C8—H8C	0.9800	C23—C24	1.527 (4)
C9—C10	1.538 (4)	C23—H23A	0.9900
C9—C13	1.542 (4)	C23—H23B	0.9900
C9—H9A	1.0000	C24—C25	1.524 (4)
C10—C17	1.520 (4)	C24—H24A	0.9900
C10—C11	1.521 (4)	C24—H24B	0.9900
C10—H10A	1.0000	C25—C26	1.527 (4)
C11—C12	1.520 (4)	C25—H25A	0.9900
C11—H11A	0.9900	C25—H25B	0.9900
C11—H11B	0.9900	C26—C28	1.518 (4)
C12—H12A	0.9900	C26—C27	1.528 (4)
C12—H12B	0.9900	C26—H26A	1.0000
C13—C14	1.534 (4)	C27—H27A	0.9800
C13—H13A	0.9900	C27—H27B	0.9800
C13—H13B	0.9900	C27—H27C	0.9800
C14—C15	1.529 (3)	C28—H28A	0.9800
C14—H14A	0.9900	C28—H28B	0.9800
C14—H14B	0.9900	C28—H28C	0.9800
C15—C17	1.537 (4)

C12—C1—C2	111.0 (2)	C14—C15—C20	116.5 (2)
C12—C1—C7	113.1 (2)	C17—C15—C20	100.38 (19)
C2—C1—C7	112.1 (2)	C16—C15—C20	109.9 (2)
C12—C1—H1A	106.7	C15—C16—H16A	109.5
C2—C1—H1A	106.7	C15—C16—H16B	109.5
C7—C1—H1A	106.7	H16A—C16—H16B	109.5
C3—C2—C1	113.0 (2)	C15—C16—H16C	109.5
C3—C2—H2A	109.0	H16A—C16—H16C	109.5
C1—C2—H2A	109.0	H16B—C16—H16C	109.5
C3—C2—H2B	109.0	C10—C17—C18	118.5 (2)
C1—C2—H2B	109.0	C10—C17—C15	115.10 (19)
H2A—C2—H2B	107.8	C18—C17—C15	104.3 (2)
C5—C3—C4	122.7 (3)	C10—C17—H17A	106.0
C5—C3—C2	121.1 (3)	C18—C17—H17A	106.0
C4—C3—C2	116.2 (3)	C15—C17—H17A	106.0
C3—C4—H4A	109.5	C17—C18—C19	102.6 (2)
C3—C4—H4B	109.5	C17—C18—H18A	111.2
H4A—C4—H4B	109.5	C19—C18—H18A	111.2
C3—C4—H4C	109.5	C17—C18—H18B	111.2
H4A—C4—H4C	109.5	C19—C18—H18B	111.2
H4B—C4—H4C	109.5	H18A—C18—H18B	109.2
C3—C5—C6	124.2 (2)	C20—C19—C18	107.4 (2)
C3—C5—H5A	117.9	C20—C19—H19A	110.2
C6—C5—H5A	117.9	C18—C19—H19A	110.2
C5—C6—C7	114.1 (2)	C20—C19—H19B	110.2
C5—C6—H6A	108.7	C18—C19—H19B	110.2
C7—C6—H6A	108.7	H19A—C19—H19B	108.5
C5—C6—H6B	108.7	C21—C20—C19	111.5 (2)
C7—C6—H6B	108.7	C21—C20—C15	119.2 (2)
H6A—C6—H6B	107.6	C19—C20—C15	103.5 (2)
C8—C7—C6	108.1 (2)	C21—C20—H20A	107.4
C8—C7—C1	110.9 (2)	C19—C20—H20A	107.4
C6—C7—C1	106.8 (2)	C15—C20—H20A	107.4
C8—C7—C9	111.8 (2)	C22—C21—C20	113.8 (2)
C6—C7—C9	110.2 (2)	C22—C21—C23	110.4 (2)
C1—C7—C9	108.90 (19)	C20—C21—C23	110.3 (2)
C7—C8—H8A	109.5	C22—C21—H21A	107.3
C7—C8—H8B	109.5	C20—C21—H21A	107.3
H8A—C8—H8B	109.5	C23—C21—H21A	107.3
C7—C8—H8C	109.5	C21—C22—H22A	109.5
H8A—C8—H8C	109.5	C21—C22—H22B	109.5
H8B—C8—H8C	109.5	H22A—C22—H22B	109.5
C10—C9—C13	111.1 (2)	C21—C22—H22C	109.5
C10—C9—C7	113.4 (2)	H22A—C22—H22C	109.5
C13—C9—C7	114.1 (2)	H22B—C22—H22C	109.5
C10—C9—H9A	105.8	C24—C23—C21	114.9 (2)
C13—C9—H9A	105.8	C24—C23—H23A	108.5
C7—C9—H9A	105.8	C21—C23—H23A	108.5
C17—C10—C11	111.6 (2)	C24—C23—H23B	108.5
C17—C10—C9	109.1 (2)	C21—C23—H23B	108.5
C11—C10—C9	110.6 (2)	H23A—C23—H23B	107.5
C17—C10—H10A	108.5	C25—C24—C23	112.0 (2)
C11—C10—H10A	108.5	C25—C24—H24A	109.2
C9—C10—H10A	108.5	C23—C24—H24A	109.2
C12—C11—C10	111.7 (2)	C25—C24—H24B	109.2
C12—C11—H11A	109.3	C23—C24—H24B	109.2
C10—C11—H11A	109.3	H24A—C24—H24B	107.9
C12—C11—H11B	109.3	C24—C25—C26	116.0 (2)
C10—C11—H11B	109.3	C24—C25—H25A	108.3
H11A—C11—H11B	107.9	C26—C25—H25A	108.3
C1—C12—C11	111.2 (2)	C24—C25—H25B	108.3
C1—C12—H12A	109.4	C26—C25—H25B	108.3
C11—C12—H12A	109.4	H25A—C25—H25B	107.4
C1—C12—H12B	109.4	C28—C26—C27	110.6 (2)
C11—C12—H12B	109.4	C28—C26—C25	112.1 (2)
H12A—C12—H12B	108.0	C27—C26—C25	109.4 (2)
C14—C13—C9	113.1 (2)	C28—C26—H26A	108.2
C14—C13—H13A	109.0	C27—C26—H26A	108.2
C9—C13—H13A	109.0	C25—C26—H26A	108.2
C14—C13—H13B	109.0	C26—C27—H27A	109.5
C9—C13—H13B	109.0	C26—C27—H27B	109.5
H13A—C13—H13B	107.8	H27A—C27—H27B	109.5
C15—C14—C13	111.2 (2)	C26—C27—H27C	109.5
C15—C14—H14A	109.4	H27A—C27—H27C	109.5
C13—C14—H14A	109.4	H27B—C27—H27C	109.5
C15—C14—H14B	109.4	C26—C28—H28A	109.5
C13—C14—H14B	109.4	C26—C28—H28B	109.5
H14A—C14—H14B	108.0	H28A—C28—H28B	109.5
C14—C15—C17	107.4 (2)	C26—C28—H28C	109.5
C14—C15—C16	110.4 (2)	H28A—C28—H28C	109.5
C17—C15—C16	112.0 (2)	H28B—C28—H28C	109.5

C12—C1—C2—C3	174.5 (2)	C13—C14—C15—C17	55.7 (3)
C7—C1—C2—C3	46.9 (3)	C13—C14—C15—C16	−66.6 (3)
C1—C2—C3—C5	−14.8 (4)	C13—C14—C15—C20	167.2 (2)
C1—C2—C3—C4	166.6 (2)	C11—C10—C17—C18	−55.8 (3)
C4—C3—C5—C6	177.6 (3)	C9—C10—C17—C18	−178.2 (2)
C2—C3—C5—C6	−1.0 (4)	C11—C10—C17—C15	179.9 (2)
C3—C5—C6—C7	−15.5 (4)	C9—C10—C17—C15	57.4 (3)
C5—C6—C7—C8	−74.9 (3)	C14—C15—C17—C10	−58.9 (3)
C5—C6—C7—C1	44.6 (3)	C16—C15—C17—C10	62.4 (3)
C5—C6—C7—C9	162.8 (2)	C20—C15—C17—C10	178.9 (2)
C12—C1—C7—C8	−70.1 (3)	C14—C15—C17—C18	169.6 (2)
C2—C1—C7—C8	56.4 (3)	C16—C15—C17—C18	−69.1 (3)
C12—C1—C7—C6	172.3 (2)	C20—C15—C17—C18	47.4 (2)
C2—C1—C7—C6	−61.1 (3)	C10—C17—C18—C19	−166.5 (2)
C12—C1—C7—C9	53.3 (3)	C15—C17—C18—C19	−37.0 (2)
C2—C1—C7—C9	179.8 (2)	C17—C18—C19—C20	12.3 (3)
C8—C7—C9—C10	70.0 (3)	C18—C19—C20—C21	145.7 (2)
C6—C7—C9—C10	−169.8 (2)	C18—C19—C20—C15	16.4 (3)
C1—C7—C9—C10	−52.9 (3)	C14—C15—C20—C21	81.9 (3)
C8—C7—C9—C13	−58.6 (3)	C17—C15—C20—C21	−162.6 (2)
C6—C7—C9—C13	61.6 (3)	C16—C15—C20—C21	−44.5 (3)
C1—C7—C9—C13	178.5 (2)	C14—C15—C20—C19	−153.6 (2)
C13—C9—C10—C17	−52.1 (3)	C17—C15—C20—C19	−38.1 (2)
C7—C9—C10—C17	177.8 (2)	C16—C15—C20—C19	79.9 (3)
C13—C9—C10—C11	−175.1 (2)	C19—C20—C21—C22	−175.7 (2)
C7—C9—C10—C11	54.7 (3)	C15—C20—C21—C22	−55.2 (3)
C17—C10—C11—C12	−176.7 (2)	C19—C20—C21—C23	59.6 (3)
C9—C10—C11—C12	−55.2 (3)	C15—C20—C21—C23	−180.0 (2)
C2—C1—C12—C11	177.1 (2)	C22—C21—C23—C24	76.7 (3)
C7—C1—C12—C11	−55.8 (3)	C20—C21—C23—C24	−156.7 (2)
C10—C11—C12—C1	56.1 (3)	C21—C23—C24—C25	−179.9 (2)
C10—C9—C13—C14	53.5 (3)	C23—C24—C25—C26	−172.8 (3)
C7—C9—C13—C14	−176.7 (2)	C24—C25—C26—C28	−62.8 (3)
C9—C13—C14—C15	−56.0 (3)	C24—C25—C26—C27	174.2 (2)

Experimental details

Crystal data
Chemical formula	C₂₈H₄₈
M_r	384.66
Crystal system, space group	Monoclinic, C2
Temperature (K)	100
a, b, c (Å)	22.216 (3), 11.7576 (15), 9.6335 (13)
β (°)	106.652 (2)
V (Å³)	2410.9 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.06
Crystal size (mm)	0.35 × 0.15 × 0.05

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.786, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	11615, 2902, 2379
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.121, 1.02
No. of reflections	2902
No. of parameters	253
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.20

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and Qmol (Gans & Shalloway, 2001), publCIF (Westrip, 2010).

Footnotes

‡Additional correspondence author, e-mail: kketuly@um.edu.my.

Acknowledgements

The authors are grateful to the University of Malaya for support of the crystallographic facility.

References

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