2-Methyl-6-(4,4,10,13,14-penta­methyl-3-oxo-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetra­deca­hydro-1H-cyclo­penta­[a]phenanthren-17-yl)hept-2-enoic acid

Arfan, M.; Rauf, A.; Tahir, M.N.; Ali, M.; Uddin, G.

doi:10.1107/S1600536811006283

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o711

doi:10.1107/S1600536811006283

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2-Methyl-6-(4,4,10,13,14-pentamethyl-3-oxo-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)hept-2-enoic acid

Mohammad Arfan,^a Abdur Rauf,^a M. Nawaz Tahir,^b ^* Mumtaz Ali ^c and Ghias Uddin ^a

^aInstitute of Chemical Sciences, University of Peshawar, Peshawar, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cDepartment of Chemistry, University of Malalkand, KPK, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 17 February 2011; accepted 19 February 2011; online 26 February 2011)

In the title compound, C₃₀H₄₆O₃, an isolation product of Pistacia integerima Stewart, the five-membered ring is nearly in the envelope form. A 6-carboxyhept-5-en-2-yl group is attached to the five-membered ring. An S(6) ring motif is formed due to intramolecular C—H⋯O hydrogen bonding. In the crystal, intermolecular O—H⋯O hydrogen bonds form carboxylate dimers with R₂²(8) ring motifs.

Related literature

For related structures and background, see: Lanfredi et al. (1975 ); Ahmad et al. (2010 ). For graph-set notation, see: Bernstein et al. (1995 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₃₀H₄₆O₃
M_r = 454.67
Tetragonal, P 4₃ 2₁ 2
a = 13.3167 (6) Å
c = 31.1595 (14) Å
V = 5525.7 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.28 × 0.15 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.935, T_max = 0.965
80888 measured reflections
3012 independent reflections
1936 reflections with I > 2σ(I)
R_int = 0.103

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.186
S = 1.03
3012 reflections
306 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3ⁱ	0.82	1.85	2.645 (7)	162
C20—H20A⋯O2	0.97	2.21	2.873 (7)	125
Symmetry code: (i) y, x, -z.

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 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006283/bq2281sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006283/bq2281Isup2.hkl

checkCIF report

Comment top

The crystal structure of Methyl (13α,14β,20S,24Z)-3-oxo-lanosta-8,24-dien-26-oate (Lanfredi et al., 1975) has been previously published which is closely related to the title compound (I. Fig. 1). This compound has been derived from the berries of Schinus molle. The title compound is isolated from the galls of Pistacia integerima Stewart which were collected from Razagran, District Dir, KPK, Pakistan. The isolated compound from the galls of Pistacia integerima Stewart by Ahmad et al., 2010 and reported as Pisticialanstenoic acid, seems the same as (I). However their spectral studies differ a litle bit from our X-ray analysis.

In (I), three six membered rings A (C1—C6), B (C5—C10) and C (C9—C14) are confirmed by different puckering parameters (Cremer & Pople, 1975). The puckering amplitude Q for the rings A, B and C have values of 0.490 (5) Å, 0.503 (4) Å and 0.540 (4) Å, θ for the rings A, B and C have values of 20.4 (6)°, 131.6 (6)° and 119.3 (4)°, ϕ for the rings A, B and C have values of 217.0 (17)°, 244.0 (7)° and 69.7 (5)°, respectively. The five membered ring D (C13—C17) has approximately envelop confirmation. The linear chain E (C20/C21/C22/C24) is planar with r. m. s. deviation of 0.0175 Å. The groups F (C18/C19/C25) and G (C23/O2/O3) are of course planar. The dihedral angle between E/F, E/G and F/G is 46.67 (5)°, 8.64 (1)° and 49.61 (5)°, respectively. There exist a strong intramolecular C—H···O and intermolecular O—H···O type H-bonding (Table 1, Fig. 2). Due to the inramolecular H-bonding S(6) ring motif is formed (Bernstein et al., 1995). The molecules are stabilized in the form of conventional carboxylate dimers with R₂²(8) ring motifs (Fig. 2).

Related literature top

For related structures and background, see: Lanfredi et al. (1975); Ahmad et al. (2010). For graph-set notation, see: Bernstein et al. (1995). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The dried and crushed galls of Pistacia chinensis var integerima (5 kg) were subjected to cold extraction with methanol (MeOH). The MeOH extract (400 g) was suspended in water and successively partitioned with n-hexane, CHCl₃, EtOAc and butanol (BuOH). The CHCl₃ fraction (10 g) was subjected to column chromatography on silica gel. The column was first eluted with n-hexane:EtOAc (100:0 → 0:100) as solvent system. A total of 13 fractions, RF-1 to RF-13 were obtained based on TLC profiles. White crude product of fraction RF-4 was separated from the solution by decantation. This crude material was washed with acetone for several times. White crystals were obtained by re-crystallization from a mixture of n-hexane:acetone (80:20). Yield: 90 mg.

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 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form carboxylate dimers with R₂²(8) ring motif.

2-Methyl-6-(4,4,10,13,14-pentamethyl-3-oxo-2,3,4,5,6,7,10,11,12,13,14,15,16,17- tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)hept-2-enoic acid top

Crystal data top

C₃₀H₄₆O₃	D_x = 1.093 Mg m⁻³
M_r = 454.67	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₃2₁2	Cell parameters from 1936 reflections
Hall symbol: P 4nw 2abw	θ = 2.0–25.5°
a = 13.3167 (6) Å	µ = 0.07 mm⁻¹
c = 31.1595 (14) Å	T = 296 K
V = 5525.7 (4) Å³	Needle, brown
Z = 8	0.28 × 0.15 × 0.10 mm
F(000) = 2000

Data collection top

Bruker Kappa APEXII CCD diffractometer	3012 independent reflections
Radiation source: fine-focus sealed tube	1936 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.103
Detector resolution: 7.50 pixels mm^-1	θ_max = 25.5°, θ_min = 2.0°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
T_min = 0.935, T_max = 0.965	l = −36→37
80888 measured reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.186	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.086P)² + 1.2062P] where P = (F_o² + 2F_c²)/3
3012 reflections	(Δ/σ)_max < 0.001
306 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₃₀H₄₆O₃	Z = 8
M_r = 454.67	Mo Kα radiation
Tetragonal, P4₃2₁2	µ = 0.07 mm⁻¹
a = 13.3167 (6) Å	T = 296 K
c = 31.1595 (14) Å	0.28 × 0.15 × 0.10 mm
V = 5525.7 (4) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	3012 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1936 reflections with I > 2σ(I)
T_min = 0.935, T_max = 0.965	R_int = 0.103
80888 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.186	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
3012 reflections	Δρ_min = −0.15 e Å⁻³
306 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.0467 (3)	0.2309 (4)	0.45862 (16)	0.153 (3)
O2	0.4258 (4)	0.3086 (4)	0.04257 (10)	0.126 (2)
O3	0.4457 (3)	0.2870 (3)	−0.02665 (10)	0.0945 (15)
C1	0.0545 (3)	0.1086 (4)	0.40354 (12)	0.0697 (16)
C2	0.0997 (4)	0.1819 (4)	0.43511 (15)	0.0853 (19)
C3	0.2098 (4)	0.1923 (6)	0.43906 (16)	0.113 (3)
C4	0.2651 (3)	0.1886 (4)	0.39648 (13)	0.0790 (19)
C5	0.2386 (3)	0.0961 (3)	0.36929 (11)	0.0543 (11)
C6	0.1235 (3)	0.0989 (3)	0.36259 (11)	0.0531 (13)
C7	0.0906 (4)	0.0152 (4)	0.33306 (13)	0.090 (2)
C8	0.1410 (3)	0.0268 (4)	0.28990 (12)	0.0683 (16)
C9	0.2428 (3)	0.0658 (3)	0.28939 (10)	0.0519 (11)
C10	0.2894 (3)	0.1031 (4)	0.32563 (11)	0.0623 (14)
C11	0.4001 (3)	0.1270 (4)	0.32455 (11)	0.0750 (18)
C12	0.4550 (3)	0.1281 (4)	0.28202 (11)	0.0690 (18)
C13	0.3835 (3)	0.1393 (3)	0.24358 (11)	0.0512 (11)
C14	0.3017 (3)	0.0559 (3)	0.24792 (11)	0.0545 (14)
C15	0.2439 (3)	0.0683 (4)	0.20556 (11)	0.0664 (15)
C16	0.3252 (4)	0.0930 (4)	0.17256 (12)	0.0714 (15)
C17	0.4235 (3)	0.1184 (3)	0.19773 (11)	0.0587 (14)
C18	0.4879 (3)	0.1963 (3)	0.17434 (12)	0.0647 (16)
C19	0.5185 (4)	0.1526 (3)	0.13015 (12)	0.0750 (16)
C20	0.5711 (4)	0.2247 (4)	0.10054 (12)	0.0767 (18)
C21	0.5919 (3)	0.1785 (3)	0.05758 (13)	0.0670 (17)
C22	0.5515 (3)	0.1957 (3)	0.01936 (12)	0.0597 (14)
C23	0.4697 (3)	0.2684 (3)	0.01166 (14)	0.0667 (17)
C24	0.5897 (3)	0.1425 (3)	−0.02023 (13)	0.0737 (17)
C25	0.5801 (4)	0.2295 (4)	0.19933 (15)	0.094 (2)
C26	0.3361 (3)	0.2445 (3)	0.24457 (13)	0.0650 (16)
C27	0.3455 (4)	−0.0514 (3)	0.24816 (14)	0.0810 (19)
C28	0.2784 (5)	0.0019 (5)	0.39218 (17)	0.112 (3)
C29	0.0378 (6)	0.0107 (5)	0.42829 (18)	0.130 (3)
C30	−0.0470 (4)	0.1500 (6)	0.38967 (15)	0.111 (3)
H2	0.37831	0.34194	0.03369	0.1506*
H3A	0.23489	0.13882	0.45730	0.1358*
H3B	0.22476	0.25557	0.45307	0.1358*
H4A	0.33683	0.18870	0.40194	0.0946*
H4B	0.24930	0.24873	0.38024	0.0946*
H6	0.11127	0.16060	0.34627	0.0637*
H7A	0.01822	0.01725	0.32950	0.1080*
H7B	0.10831	−0.04913	0.34551	0.1080*
H8A	0.14170	−0.03851	0.27608	0.0820*
H8B	0.09968	0.07064	0.27243	0.0820*
H11A	0.43374	0.07888	0.34294	0.0902*
H11B	0.40888	0.19258	0.33758	0.0902*
H12A	0.49270	0.06612	0.27900	0.0831*
H12B	0.50259	0.18325	0.28186	0.0831*
H15A	0.20905	0.00683	0.19801	0.0794*
H15B	0.19532	0.12242	0.20762	0.0794*
H16A	0.30481	0.14991	0.15518	0.0854*
H16B	0.33623	0.03599	0.15377	0.0854*
H17	0.46301	0.05644	0.19923	0.0702*
H18	0.44620	0.25568	0.16920	0.0777*
H19A	0.56223	0.09537	0.13492	0.0898*
H19B	0.45857	0.12811	0.11589	0.0898*
H20A	0.52964	0.28396	0.09671	0.0920*
H20B	0.63392	0.24570	0.11349	0.0920*
H21	0.64161	0.12939	0.05775	0.0805*
H24A	0.63824	0.09279	−0.01204	0.1105*
H24B	0.62052	0.19041	−0.03912	0.1105*
H24C	0.53461	0.11059	−0.03468	0.1105*
H25A	0.62046	0.27268	0.18170	0.1404*
H25B	0.61863	0.17158	0.20747	0.1404*
H25C	0.55949	0.26512	0.22462	0.1404*
H26A	0.29602	0.25408	0.21928	0.0973*
H26B	0.38814	0.29424	0.24548	0.0973*
H26C	0.29438	0.25074	0.26957	0.0973*
H27A	0.38542	−0.06134	0.22286	0.1215*
H27B	0.29170	−0.09931	0.24862	0.1215*
H27C	0.38672	−0.06017	0.27316	0.1215*
H28A	0.25466	−0.05697	0.37756	0.1687*
H28B	0.25480	0.00123	0.42129	0.1687*
H28C	0.35044	0.00259	0.39196	0.1687*
H29A	0.01134	−0.03938	0.40925	0.1956*
H29B	−0.00884	0.02219	0.45125	0.1956*
H29C	0.10060	−0.01211	0.43991	0.1956*
H30A	−0.07966	0.10242	0.37124	0.1662*
H30B	−0.03736	0.21201	0.37448	0.1662*
H30C	−0.08784	0.16178	0.41454	0.1662*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.090 (3)	0.218 (6)	0.152 (4)	−0.011 (3)	0.022 (3)	−0.121 (4)
O2	0.133 (4)	0.169 (4)	0.075 (2)	0.079 (3)	0.009 (2)	−0.017 (3)
O3	0.122 (3)	0.100 (3)	0.0614 (18)	0.021 (2)	0.0003 (19)	−0.0075 (18)
C1	0.066 (3)	0.098 (3)	0.045 (2)	−0.016 (3)	0.010 (2)	−0.017 (2)
C2	0.068 (3)	0.123 (4)	0.065 (3)	−0.005 (3)	0.007 (2)	−0.037 (3)
C3	0.067 (3)	0.191 (7)	0.082 (3)	−0.007 (4)	0.001 (3)	−0.073 (4)
C4	0.059 (3)	0.109 (4)	0.069 (3)	−0.007 (3)	−0.003 (2)	−0.036 (3)
C5	0.063 (2)	0.061 (2)	0.0389 (17)	0.006 (2)	−0.0009 (18)	−0.0028 (18)
C6	0.052 (2)	0.070 (3)	0.0373 (17)	−0.009 (2)	0.0011 (16)	−0.0099 (18)
C7	0.094 (4)	0.116 (4)	0.061 (2)	−0.042 (3)	0.019 (3)	−0.036 (3)
C8	0.075 (3)	0.080 (3)	0.050 (2)	−0.013 (2)	0.004 (2)	−0.022 (2)
C9	0.064 (2)	0.053 (2)	0.0388 (18)	−0.0026 (19)	0.0047 (18)	−0.0079 (17)
C10	0.053 (2)	0.093 (3)	0.0408 (19)	−0.002 (2)	−0.0015 (18)	−0.004 (2)
C11	0.051 (3)	0.129 (4)	0.045 (2)	0.007 (3)	−0.0021 (19)	0.000 (2)
C12	0.057 (3)	0.101 (4)	0.049 (2)	0.006 (2)	0.002 (2)	0.001 (2)
C13	0.053 (2)	0.058 (2)	0.0425 (19)	0.0116 (18)	0.0040 (17)	0.0011 (17)
C14	0.068 (3)	0.051 (2)	0.0445 (19)	0.0072 (19)	0.0025 (19)	−0.0040 (18)
C15	0.076 (3)	0.080 (3)	0.0431 (19)	−0.006 (2)	0.001 (2)	−0.012 (2)
C16	0.092 (3)	0.080 (3)	0.0421 (19)	0.000 (3)	−0.003 (2)	−0.008 (2)
C17	0.067 (3)	0.058 (2)	0.051 (2)	0.018 (2)	0.011 (2)	0.0031 (18)
C18	0.075 (3)	0.058 (3)	0.061 (2)	0.011 (2)	0.011 (2)	0.007 (2)
C19	0.090 (3)	0.073 (3)	0.062 (2)	0.005 (3)	0.027 (2)	0.006 (2)
C20	0.095 (4)	0.078 (3)	0.057 (2)	−0.001 (3)	0.012 (2)	0.004 (2)
C21	0.074 (3)	0.056 (3)	0.071 (3)	0.000 (2)	0.023 (2)	0.008 (2)
C22	0.064 (3)	0.055 (2)	0.060 (2)	−0.008 (2)	0.018 (2)	−0.002 (2)
C23	0.073 (3)	0.064 (3)	0.063 (3)	−0.006 (2)	0.019 (2)	−0.010 (2)
C24	0.075 (3)	0.069 (3)	0.077 (3)	−0.008 (2)	0.024 (2)	−0.014 (2)
C25	0.088 (4)	0.112 (4)	0.081 (3)	−0.016 (3)	0.011 (3)	0.005 (3)
C26	0.069 (3)	0.059 (3)	0.067 (2)	0.005 (2)	0.015 (2)	−0.008 (2)
C27	0.114 (4)	0.060 (3)	0.069 (3)	0.018 (3)	0.023 (3)	0.001 (2)
C28	0.120 (5)	0.110 (5)	0.107 (4)	0.045 (4)	0.025 (4)	0.042 (4)
C29	0.171 (7)	0.131 (5)	0.089 (4)	−0.039 (5)	0.066 (4)	0.004 (4)
C30	0.053 (3)	0.203 (7)	0.077 (3)	−0.010 (4)	0.009 (2)	−0.029 (4)

Geometric parameters (Å, º) top

O1—C2	1.209 (7)	C6—H6	0.9800
O2—C23	1.247 (6)	C7—H7A	0.9700
O3—C23	1.260 (5)	C7—H7B	0.9700
O2—H2	0.8200	C8—H8A	0.9700
C1—C2	1.511 (7)	C8—H8B	0.9700
C1—C6	1.578 (5)	C11—H11A	0.9700
C1—C30	1.522 (7)	C11—H11B	0.9700
C1—C29	1.531 (8)	C12—H12A	0.9700
C2—C3	1.478 (8)	C12—H12B	0.9700
C3—C4	1.518 (6)	C15—H15A	0.9700
C4—C5	1.536 (6)	C15—H15B	0.9700
C5—C6	1.547 (6)	C16—H16A	0.9700
C5—C28	1.537 (7)	C16—H16B	0.9700
C5—C10	1.522 (5)	C17—H17	0.9800
C6—C7	1.510 (6)	C18—H18	0.9800
C7—C8	1.511 (6)	C19—H19A	0.9700
C8—C9	1.452 (6)	C19—H19B	0.9700
C9—C10	1.381 (5)	C20—H20A	0.9700
C9—C14	1.517 (5)	C20—H20B	0.9700
C10—C11	1.509 (6)	C21—H21	0.9300
C11—C12	1.514 (5)	C24—H24A	0.9600
C12—C13	1.537 (5)	C24—H24B	0.9600
C13—C17	1.550 (5)	C24—H24C	0.9600
C13—C26	1.537 (6)	C25—H25A	0.9600
C13—C14	1.562 (6)	C25—H25B	0.9600
C14—C15	1.537 (5)	C25—H25C	0.9600
C14—C27	1.543 (6)	C26—H26A	0.9600
C15—C16	1.529 (6)	C26—H26B	0.9600
C16—C17	1.563 (6)	C26—H26C	0.9600
C17—C18	1.531 (6)	C27—H27A	0.9600
C18—C25	1.520 (6)	C27—H27B	0.9600
C18—C19	1.549 (5)	C27—H27C	0.9600
C19—C20	1.505 (6)	C28—H28A	0.9600
C20—C21	1.499 (6)	C28—H28B	0.9600
C21—C22	1.327 (6)	C28—H28C	0.9600
C22—C23	1.477 (6)	C29—H29A	0.9600
C22—C24	1.511 (6)	C29—H29B	0.9600
C3—H3A	0.9700	C29—H29C	0.9600
C3—H3B	0.9700	C30—H30A	0.9600
C4—H4A	0.9700	C30—H30B	0.9600
C4—H4B	0.9700	C30—H30C	0.9600

O2···O3ⁱ	2.645 (7)	H11B···C4	2.6500
O2···C20	2.873 (7)	H11B···H4A	2.2200
O3···O2ⁱ	2.645 (7)	H12A···C27	2.6900
O1···H30C	2.4400	H12A···H17	2.5200
O1···H30B	2.8600	H12A···H27C	2.2000
O1···H3Aⁱⁱ	2.8900	H12B···C25	2.8400
O1···H29B	2.8900	H12B···H25C	2.2200
O2···H20A	2.2100	H12B···H26B	2.4100
O2···H2ⁱ	2.7800	H15A···C8	3.0100
O2···H30Aⁱⁱⁱ	2.8900	H15A···H27B	2.3900
O3···H24B	2.6900	H15B···C8	2.9500
O3···H25B^iv	2.7800	H15B···C26	2.7400
O3···H8B^v	2.8000	H15B···H8B	2.4900
O3···H24C	2.6400	H15B···H26A	2.2400
O3···H2ⁱ	1.8500	H15B···C21^x	3.0200
C10···C26	3.211 (6)	H16A···C19	2.9500
C11···C27	3.441 (6)	H16A···C26	3.0900
C12···C25	3.352 (6)	H16A···H18	2.3900
C20···O2	2.873 (7)	H16A···H19B	2.4000
C25···C26	3.548 (7)	H16A···H26A	2.4300
C25···C12	3.352 (6)	H16B···C19	2.9700
C26···C25	3.548 (7)	H16B···H19B	2.3600
C26···C10	3.211 (6)	H16B···H27A	2.6000
C27···C11	3.441 (6)	H16B···C11^iv	3.1000
C28···C29	3.398 (10)	H16B···H11A^iv	2.5900
C29···C28	3.398 (10)	H17···C27	2.6100
C1···H28B	3.0800	H17···H12A	2.5200
C3···H29C	3.0900	H17···H19A	2.4600
C3···H28B	2.6700	H17···H25B	2.5900
C4···H11B	2.6500	H17···H27A	2.0200
C7···H29A	2.7000	H17···H24C^vi	2.3600
C7···H28A	2.7600	H18···C26	2.7700
C7···H30A	2.8100	H18···H16A	2.3900
C8···H27B	2.9200	H18···H20A	2.5500
C8···H15B	2.9500	H18···H26A	2.5400
C8···H15A	3.0100	H18···H26B	2.5500
C9···H6	2.7900	H18···C30ⁱⁱⁱ	3.0600
C9···H26C	2.6300	H18···H30Cⁱⁱⁱ	2.5400
C10···H26C	2.6300	H19A···H17	2.4600
C10···H27C	3.0100	H19A···H25B	2.5900
C11···H26C	2.7600	H19B···C16	2.5500
C11···H16B^vi	3.1000	H19B···H16A	2.4000
C11···H27C	2.9700	H19B···H16B	2.3600
C11···H4A	2.6800	H20A···O2	2.2100
C11···H28C	2.7600	H20A···C23	2.7800
C12···H27C	2.6800	H20A···H18	2.5500
C12···H25C	2.9100	H20B···C25	2.7800
C13···H25C	2.9400	H20B···H25A	2.1600
C15···H26A	2.6000	H21···H24A	2.2300
C15···H8A	2.9500	H24A···H21	2.2300
C15···H8B	2.8300	H24B···O3	2.6900
C16···H19B	2.5500	H24B···H26C^v	2.5200
C16···H27A	2.7100	H24C···O3	2.6400
C16···H26A	2.6200	H24C···H17^iv	2.3600
C17···H27A	2.5700	H25A···C20	2.6900
C18···H26A	3.0100	H25A···H20B	2.1600
C18···H26B	2.8900	H25B···H17	2.5900
C19···H16A	2.9500	H25B···H19A	2.5900
C19···H16B	2.9700	H25B···O3^vi	2.7800
C20···H25A	2.6900	H25C···C12	2.9100
C21···H26A^v	2.9800	H25C···C13	2.9400
C21···H15B^v	3.0200	H25C···C26	3.0500
C23···H8B^v	2.9500	H25C···H12B	2.2200
C23···H20A	2.7800	H25C···H26B	2.4000
C23···H2ⁱ	2.6500	H26A···C15	2.6000
C24···H26C^v	3.0700	H26A···C16	2.6200
C25···H20B	2.7800	H26A···C18	3.0100
C25···H12B	2.8400	H26A···H15B	2.2400
C25···H26B	3.0600	H26A···H16A	2.4300
C26···H18	2.7700	H26A···H18	2.5400
C26···H15B	2.7400	H26A···C21^x	2.9800
C26···H16A	3.0900	H26B···C18	2.8900
C26···H25C	3.0500	H26B···C25	3.0600
C27···H17	2.6100	H26B···H12B	2.4100
C27···H8A	2.8600	H26B···H18	2.5500
C27···H12A	2.6900	H26B···H25C	2.4000
C28···H3A	2.7900	H26C···C9	2.6300
C28···H11A	2.7700	H26C···C10	2.6300
C28···H29C	2.8000	H26C···C11	2.7600
C28···H7B	2.7800	H26C···C24^x	3.0700
C29···H7A	3.0900	H26C···H24B^x	2.5200
C29···H7B	2.8600	H27A···C16	2.7100
C29···H28B	2.9000	H27A···C17	2.5700
C30···H7A	2.7200	H27A···H16B	2.6000
C30···H18^vii	3.0600	H27A···H17	2.0200
H2···O2ⁱ	2.7800	H27B···C8	2.9200
H2···O3ⁱ	1.8500	H27B···H8A	2.3200
H2···C23ⁱ	2.6500	H27B···H15A	2.3900
H2···H2ⁱ	2.2100	H27B···H3B^xi	2.4600
H3A···C28	2.7900	H27C···C10	3.0100
H3A···H28B	2.1600	H27C···C11	2.9700
H3A···O1ⁱⁱ	2.8900	H27C···C12	2.6800
H3B···H27B^viii	2.4600	H27C···H12A	2.2000
H4A···C11	2.6800	H28A···C7	2.7600
H4A···H11B	2.2200	H28A···H7B	2.1900
H4A···H28C	2.5000	H28A···H4B^xi	2.6000
H4B···H6	2.4200	H28B···C1	3.0800
H4B···H28A^viii	2.6000	H28B···C3	2.6700
H6···C9	2.7900	H28B···C29	2.9000
H6···H4B	2.4200	H28B···H3A	2.1600
H6···H8B	2.6000	H28B···H29C	2.1400
H6···H30B	2.2700	H28C···C11	2.7600
H7A···C29	3.0900	H28C···H4A	2.5000
H7A···C30	2.7200	H28C···H11A	2.1400
H7A···H29A	2.6000	H29A···C7	2.7000
H7A···H30A	2.1600	H29A···H7A	2.6000
H7B···C28	2.7800	H29A···H7B	2.3700
H7B···C29	2.8600	H29A···H30A	2.5400
H7B···H28A	2.1900	H29B···O1	2.8900
H7B···H29A	2.3700	H29B···H30C	2.4200
H8A···C15	2.9500	H29C···C3	3.0900
H8A···C27	2.8600	H29C···C28	2.8000
H8A···H27B	2.3200	H29C···H28B	2.1400
H8A···H8A^ix	2.5300	H30A···C7	2.8100
H8B···C15	2.8300	H30A···H7A	2.1600
H8B···H6	2.6000	H30A···H29A	2.5400
H8B···H15B	2.4900	H30A···O2^vii	2.8900
H8B···O3^x	2.8000	H30B···O1	2.8600
H8B···C23^x	2.9500	H30B···H6	2.2700
H11A···C28	2.7700	H30C···O1	2.4400
H11A···H28C	2.1400	H30C···H29B	2.4200
H11A···H16B^vi	2.5900	H30C···H18^vii	2.5400

C23—O2—H2	109.00	H8A—C8—H8B	107.00
C2—C1—C29	106.3 (4)	C10—C11—H11A	107.00
C2—C1—C30	107.7 (4)	C10—C11—H11B	107.00
C2—C1—C6	110.3 (4)	C12—C11—H11A	108.00
C6—C1—C30	108.5 (3)	C12—C11—H11B	107.00
C29—C1—C30	108.8 (5)	H11A—C11—H11B	107.00
C6—C1—C29	115.0 (4)	C11—C12—H12A	109.00
O1—C2—C3	118.6 (5)	C11—C12—H12B	109.00
C1—C2—C3	120.7 (5)	C13—C12—H12A	109.00
O1—C2—C1	120.7 (5)	C13—C12—H12B	109.00
C2—C3—C4	113.9 (4)	H12A—C12—H12B	108.00
C3—C4—C5	113.4 (4)	C14—C15—H15A	111.00
C4—C5—C6	106.4 (3)	C14—C15—H15B	111.00
C4—C5—C10	110.0 (3)	C16—C15—H15A	111.00
C6—C5—C10	108.6 (3)	C16—C15—H15B	111.00
C6—C5—C28	115.1 (4)	H15A—C15—H15B	109.00
C10—C5—C28	108.1 (4)	C15—C16—H16A	110.00
C4—C5—C28	108.6 (4)	C15—C16—H16B	110.00
C1—C6—C5	118.0 (3)	C17—C16—H16A	110.00
C5—C6—C7	110.6 (3)	C17—C16—H16B	110.00
C1—C6—C7	112.6 (4)	H16A—C16—H16B	108.00
C6—C7—C8	109.8 (4)	C13—C17—H17	107.00
C7—C8—C9	117.5 (3)	C16—C17—H17	107.00
C8—C9—C14	117.5 (3)	C18—C17—H17	107.00
C10—C9—C14	119.7 (3)	C17—C18—H18	108.00
C8—C9—C10	122.6 (3)	C19—C18—H18	108.00
C5—C10—C11	117.9 (3)	C25—C18—H18	108.00
C9—C10—C11	119.8 (3)	C18—C19—H19A	108.00
C5—C10—C9	120.6 (4)	C18—C19—H19B	108.00
C10—C11—C12	119.6 (3)	C20—C19—H19A	108.00
C11—C12—C13	112.6 (3)	C20—C19—H19B	108.00
C12—C13—C17	119.2 (3)	H19A—C19—H19B	107.00
C12—C13—C26	109.1 (3)	C19—C20—H20A	109.00
C14—C13—C17	101.1 (3)	C19—C20—H20B	109.00
C14—C13—C26	111.1 (3)	C21—C20—H20A	109.00
C17—C13—C26	108.9 (3)	C21—C20—H20B	109.00
C12—C13—C14	107.2 (3)	H20A—C20—H20B	108.00
C9—C14—C13	111.9 (3)	C20—C21—H21	115.00
C9—C14—C27	105.8 (3)	C22—C21—H21	115.00
C13—C14—C15	101.5 (3)	C22—C24—H24A	109.00
C13—C14—C27	113.3 (3)	C22—C24—H24B	109.00
C15—C14—C27	107.0 (3)	C22—C24—H24C	109.00
C9—C14—C15	117.6 (3)	H24A—C24—H24B	109.00
C14—C15—C16	104.3 (3)	H24A—C24—H24C	110.00
C15—C16—C17	107.6 (3)	H24B—C24—H24C	109.00
C13—C17—C18	120.7 (3)	C18—C25—H25A	109.00
C16—C17—C18	112.2 (3)	C18—C25—H25B	109.00
C13—C17—C16	102.3 (3)	C18—C25—H25C	109.00
C17—C18—C19	108.4 (3)	H25A—C25—H25B	109.00
C17—C18—C25	114.0 (3)	H25A—C25—H25C	110.00
C19—C18—C25	110.6 (4)	H25B—C25—H25C	109.00
C18—C19—C20	115.3 (3)	C13—C26—H26A	109.00
C19—C20—C21	111.8 (4)	C13—C26—H26B	109.00
C20—C21—C22	131.0 (4)	C13—C26—H26C	109.00
C21—C22—C24	121.0 (4)	H26A—C26—H26B	110.00
C23—C22—C24	115.0 (3)	H26A—C26—H26C	109.00
C21—C22—C23	123.9 (4)	H26B—C26—H26C	110.00
O2—C23—C22	120.1 (4)	C14—C27—H27A	109.00
O3—C23—C22	118.0 (4)	C14—C27—H27B	109.00
O2—C23—O3	121.9 (4)	C14—C27—H27C	109.00
C2—C3—H3A	109.00	H27A—C27—H27B	110.00
C2—C3—H3B	109.00	H27A—C27—H27C	109.00
C4—C3—H3A	109.00	H27B—C27—H27C	110.00
C4—C3—H3B	109.00	C5—C28—H28A	109.00
H3A—C3—H3B	108.00	C5—C28—H28B	109.00
C3—C4—H4A	109.00	C5—C28—H28C	109.00
C3—C4—H4B	109.00	H28A—C28—H28B	109.00
C5—C4—H4A	109.00	H28A—C28—H28C	109.00
C5—C4—H4B	109.00	H28B—C28—H28C	110.00
H4A—C4—H4B	108.00	C1—C29—H29A	109.00
C1—C6—H6	105.00	C1—C29—H29B	109.00
C5—C6—H6	105.00	C1—C29—H29C	109.00
C7—C6—H6	105.00	H29A—C29—H29B	110.00
C6—C7—H7A	110.00	H29A—C29—H29C	109.00
C6—C7—H7B	110.00	H29B—C29—H29C	109.00
C8—C7—H7A	110.00	C1—C30—H30A	109.00
C8—C7—H7B	110.00	C1—C30—H30B	109.00
H7A—C7—H7B	108.00	C1—C30—H30C	109.00
C7—C8—H8A	108.00	H30A—C30—H30B	109.00
C7—C8—H8B	108.00	H30A—C30—H30C	110.00
C9—C8—H8A	108.00	H30B—C30—H30C	109.00
C9—C8—H8B	108.00

C6—C1—C2—O1	149.9 (5)	C10—C9—C14—C15	−148.9 (4)
C6—C1—C2—C3	−32.5 (6)	C10—C9—C14—C27	91.7 (5)
C29—C1—C2—O1	−84.9 (6)	C5—C10—C11—C12	176.1 (4)
C29—C1—C2—C3	92.7 (6)	C9—C10—C11—C12	11.1 (7)
C30—C1—C2—O1	31.6 (7)	C10—C11—C12—C13	19.5 (7)
C30—C1—C2—C3	−150.8 (5)	C11—C12—C13—C14	−52.8 (5)
C2—C1—C6—C5	40.4 (5)	C11—C12—C13—C17	−166.6 (4)
C2—C1—C6—C7	171.2 (4)	C11—C12—C13—C26	67.6 (5)
C29—C1—C6—C5	−79.7 (5)	C12—C13—C14—C9	59.9 (4)
C29—C1—C6—C7	51.1 (5)	C12—C13—C14—C15	−173.9 (3)
C30—C1—C6—C5	158.2 (4)	C12—C13—C14—C27	−59.6 (4)
C30—C1—C6—C7	−71.0 (5)	C17—C13—C14—C9	−174.6 (3)
O1—C2—C3—C4	−142.5 (6)	C17—C13—C14—C15	−48.4 (4)
C1—C2—C3—C4	39.9 (8)	C17—C13—C14—C27	65.9 (4)
C2—C3—C4—C5	−52.6 (7)	C26—C13—C14—C9	−59.2 (4)
C3—C4—C5—C6	57.3 (5)	C26—C13—C14—C15	67.0 (4)
C3—C4—C5—C10	174.7 (4)	C26—C13—C14—C27	−178.7 (3)
C3—C4—C5—C28	−67.1 (5)	C12—C13—C17—C16	156.9 (4)
C4—C5—C6—C1	−52.9 (5)	C12—C13—C17—C18	−77.8 (5)
C4—C5—C6—C7	175.4 (3)	C14—C13—C17—C16	39.9 (4)
C10—C5—C6—C1	−171.3 (4)	C14—C13—C17—C18	165.2 (3)
C10—C5—C6—C7	57.1 (4)	C26—C13—C17—C16	−77.1 (4)
C28—C5—C6—C1	67.4 (5)	C26—C13—C17—C18	48.2 (5)
C28—C5—C6—C7	−64.2 (4)	C9—C14—C15—C16	159.8 (4)
C4—C5—C10—C9	−145.8 (4)	C13—C14—C15—C16	37.5 (4)
C4—C5—C10—C11	49.4 (5)	C27—C14—C15—C16	−81.5 (4)
C6—C5—C10—C9	−29.7 (6)	C14—C15—C16—C17	−12.7 (5)
C6—C5—C10—C11	165.4 (4)	C15—C16—C17—C13	−17.3 (5)
C28—C5—C10—C9	95.8 (5)	C15—C16—C17—C18	−148.0 (4)
C28—C5—C10—C11	−69.1 (6)	C13—C17—C18—C19	178.4 (3)
C1—C6—C7—C8	165.3 (4)	C13—C17—C18—C25	54.8 (5)
C5—C6—C7—C8	−60.3 (5)	C16—C17—C18—C19	−61.0 (4)
C6—C7—C8—C9	35.0 (6)	C16—C17—C18—C25	175.4 (4)
C7—C8—C9—C10	−7.9 (7)	C17—C18—C19—C20	172.5 (4)
C7—C8—C9—C14	166.7 (4)	C25—C18—C19—C20	−61.9 (5)
C8—C9—C10—C5	5.7 (7)	C18—C19—C20—C21	−176.2 (4)
C8—C9—C10—C11	170.3 (4)	C19—C20—C21—C22	109.0 (5)
C14—C9—C10—C5	−168.8 (4)	C20—C21—C22—C23	−1.6 (7)
C14—C9—C10—C11	−4.2 (7)	C20—C21—C22—C24	176.6 (4)
C8—C9—C14—C13	153.2 (4)	C21—C22—C23—O2	−9.1 (7)
C8—C9—C14—C15	36.4 (5)	C21—C22—C23—O3	171.7 (4)
C8—C9—C14—C27	−83.0 (4)	C24—C22—C23—O2	172.6 (4)
C10—C9—C14—C13	−32.1 (5)	C24—C22—C23—O3	−6.7 (6)

Symmetry codes: (i) y, x, −z; (ii) y, x, −z+1; (iii) −y+1/2, x+1/2, z−1/4; (iv) −y+1/2, x−1/2, z−1/4; (v) x+1/2, −y+1/2, −z+1/4; (vi) y+1/2, −x+1/2, z+1/4; (vii) y−1/2, −x+1/2, z+1/4; (viii) −x+1/2, y+1/2, −z+3/4; (ix) −y, −x, −z+1/2; (x) x−1/2, −y+1/2, −z+1/4; (xi) −x+1/2, y−1/2, −z+3/4.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.82	1.85	2.645 (7)	162
C20—H20A···O2	0.97	2.21	2.873 (7)	125

Symmetry code: (i) y, x, −z.

Experimental details

Crystal data
Chemical formula	C₃₀H₄₆O₃
M_r	454.67
Crystal system, space group	Tetragonal, P4₃2₁2
Temperature (K)	296
a, c (Å)	13.3167 (6), 31.1595 (14)
V (Å³)	5525.7 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.28 × 0.15 × 0.10

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.935, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	80888, 3012, 1936
R_int	0.103
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.186, 1.03
No. of reflections	3012
No. of parameters	306
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.15

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.82	1.85	2.645 (7)	162
C20—H20A···O2	0.97	2.21	2.873 (7)	125

Symmetry code: (i) y, x, −z.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

Ahmad, S., Ali, M., Ansari, S. H. & Ahmad, F. (2010). J. Saudi Chem. Soc. 14, 409–412. Web of Science CrossRef CAS Google Scholar
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Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Lanfredi, A. M. M., Tiripicchio, A., Camellini, M. T. & Scapini, G. (1975). Cryst. Struct. Commun. 4, 551–554. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 3| March 2011| Page o711

doi:10.1107/S1600536811006283

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Methyl-6-(4,4,10,13,14-penta­methyl-3-oxo-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetra­deca­hydro-1H-cyclo­penta­[a]phenanthren-17-yl)hept-2-enoic acid

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Methyl-6-(4,4,10,13,14-pentamethyl-3-oxo-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)hept-2-enoic acid