(4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octa­hydro­phenan­thren-2-yl benzoate

Oubabi, R.; Auhmani, A.; Ait Itto, M.Y.; Auhmani, A.; Daran, J.-C.

doi:10.1107/S1600536814015827

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 8| August 2014| Pages o866-o867

doi:10.1107/S1600536814015827

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(4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl benzoate

Radouane Oubabi,^a Aziz Auhmani,^a My Youssef Ait Itto,^a Abdelwahed Auhmani ^a and Jean-Claude Daran ^b ^*

^aLaboratoire de Synthése Organique et Physico-Chimie Moléculaire, Département de Chimie, Faculté des Sciences Semlalia, BP 2390 Marrakech 40000, Morocco, and ^bLaboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France
^*Correspondence e-mail: a.auhmani@uca.ma

Edited by S. Bernès, UANL, México (Received 24 June 2014; accepted 7 July 2014; online 11 July 2014)

The title compound, C₂₇H₃₄O₂, was hemisynthesized through direct benzoylation of the naturally occurring meroterpene totarol. The central fused six-membered ring has a half-chair conformation, whereas the terminal six-membered ring displays a chair conformation. The dihedral angle between the fused benzene ring and the benzoyl benzene ring is 73.05 (14)°. The S,S chirality of the molecule is consistent with the synthetic pathway, and confirmed by the refinement of the Flack parameter.

Keywords: crystal structure.

CCDC reference: 1012402

Related literature

For the synthesis and biological activity of totarol [systematic name: (4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol], see: Short & Stromberg (1937 ); Barrero et al. (2003 ); Haraguchi et al. (1996 ); Bernabeu et al. (2002 ); Marcos et al. (2003 ); Tacon et al. (2012 ). For conformational analysis and absolute configuration determination, see: Cremer & Pople (1975 ); Flack (1983 ); Flack & Bernardinelli (2000 ); Parsons et al. (2013 ); Spek (2009 ). For related structures, see: Zeroual et al. (2008 ); Oubabi et al. (2014 ); Pettit et al. (2004 ).

Experimental

Crystal data

C₂₇H₃₄O₂
M_r = 390.54
Monoclinic, P 2₁
a = 7.7369 (3) Å
b = 7.2079 (4) Å
c = 20.2499 (9) Å
β = 99.816 (4)°
V = 1112.74 (9) Å³
Z = 2
Cu Kα radiation
μ = 0.55 mm⁻¹
T = 180 K
0.50 × 0.25 × 0.07 mm

Data collection

Agilent Xcalibur (Eos, Gemini ultra) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.689, T_max = 1.0
9197 measured reflections
3116 independent reflections
2926 reflections with I > 2σ(I)
R_int = 0.033
θ_max = 60.8°

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.095
S = 1.04
3116 reflections
267 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack x determined using 1138 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013)
Absolute structure parameter: −0.11 (17)

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL2013.

Supporting information

CCDC reference: 1012402

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814015827/bh2501sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814015827/bh2501Isup2.hkl

checkCIF report

Results and discussion top

Totarol is a naturally produced terpenoid isolated from several plants such as Podocarpus totara (Short & Stromberg, 1937) and Tetraclinis articulata (Barrero et al., 2003). It has been attracting great interest because of its biological properties ranging from antimicrobial (Haraguchi et al., 1996), anti-oxidant (Bernabeu et al., 2002), anti-inflammatory, analgesic, anti-tumoral (Marcos et al., 2003) to anti-plasmodial (Tacon et al., 2012).

In our ongoing studies on the synthesis of totarol derivatives of potential interest, we carried out the reaction of totarol with benzoyl chloride in pyridine, which provides the expected benzoylated product, (4bS,8aS)-1-isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl benzoate, as colorless crystals in 92% yield. Its structure was characterized by mass and NMR spectroscopy, and was fully confirmed by an X-ray single crystal structure analysis.

This compound is built up from three fused six-membered rings, an unsaturated benzene ring (I) and two saturated rings (II) and (III) (Fig. 1). The central saturated ring (II) has a half chair conformation with puckering parameters Q = 0.527 (3) Å, θ= 48.6 (3)° and ϕ= 128.9 (4)° (Cremer & Pople, 1975), whereas the second saturated six-membered ring, (III), displays a chair conformation with puckering parameters Q = 0.546 (3) Å, θ= 175.8 (3)° and ϕ= 301 (4)°. Similar conformation for the three fused rings has been reported previously with hydroxyl substituent or methyl acetate in place of the benzoate of the title compound (Zeroual et al., 2008; Oubabi et al., 2014), and with either an hydroxyl or a methoxy substituent on the central ring (Pettit et al., 2004).

The 4bS,8aS absolute configuration is deduced from the synthetic pathway. Although the Flack (Flack, 1983; Flack & Bernardinelli, 2000; Parsons et al., 2013) and Hooft parameters (Spek, 2009) display large standard deviations, their values, -0.11 (17) and 0.09 (15), confirmed the expected absolute configuration.

Experimental top

Synthesis and crystallization top

A solution of totarol (110 mg, 0.384 mmol) in benzoyl chloride (3 mL) and pyridine (20 mL) was refluxed for 24 hours. After cooling, the mixture was acidified with HCl (1N solution), and then extracted with ether (3×20 mL). The organic layer was washed with water, dried on anhydrous Na₂SO₄ and then evaporated under reduced pressure. The obtained residue was chromatographed on a silica gel column using hexane and ethyl acetate (97/3) as eluent, to give the title compound in 92 % yield. X-ray quality crystals were obtained by slow evaporation from a petroleum ether solution of the title compound.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Related literature top

For the synthesis and the biological activity of totarol [systematic name: (4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol], see: Short & Stromberg (1937); Barrero et al. (2003); Haraguchi et al. (1996); Bernabeu et al. (2002); Marcos et al. (2003); Tacon et al. (2012). For conformational analysis and absolute configuration determination, see: Cremer & Pople (1975); Flack (1983); Flack & Bernardinelli (2000); Parsons et al. (2013); Spek (2009). For related structures, see: Zeroual et al. (2008); Oubabi et al. (2014); Pettit et al. (2004).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular view of the title compound with ellipsoids for non-H atoms drawn at the 50% probability level. H atoms are represented as small circle of arbitrary radii.

(4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl benzoate top

Crystal data top

C₂₇H₃₄O₂	F(000) = 424
M_r = 390.54	D_x = 1.166 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
a = 7.7369 (3) Å	Cell parameters from 4294 reflections
b = 7.2079 (4) Å	θ = 4.4–60.4°
c = 20.2499 (9) Å	µ = 0.55 mm⁻¹
β = 99.816 (4)°	T = 180 K
V = 1112.74 (9) Å³	Flattened, colourless
Z = 2	0.50 × 0.25 × 0.07 mm

Data collection top

Agilent Xcalibur (Eos, Gemini ultra) diffractometer	3116 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2926 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.033
Detector resolution: 16.1978 pixels mm^-1	θ_max = 60.8°, θ_min = 4.4°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −8→7
T_min = 0.689, T_max = 1.0	l = −22→22
9197 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0501P)² + 0.1662P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3116 reflections	Δρ_max = 0.13 e Å⁻³
267 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack x determined using 1138 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
0 constraints	Absolute structure parameter: −0.11 (17)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₇H₃₄O₂	V = 1112.74 (9) Å³
M_r = 390.54	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 7.7369 (3) Å	µ = 0.55 mm⁻¹
b = 7.2079 (4) Å	T = 180 K
c = 20.2499 (9) Å	0.50 × 0.25 × 0.07 mm
β = 99.816 (4)°

Data collection top

Agilent Xcalibur (Eos, Gemini ultra) diffractometer	3116 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2926 reflections with I > 2σ(I)
T_min = 0.689, T_max = 1.0	R_int = 0.033
9197 measured reflections	θ_max = 60.8°

Refinement top

R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.095	Δρ_max = 0.13 e Å⁻³
S = 1.04	Δρ_min = −0.21 e Å⁻³
3116 reflections	Absolute structure: Flack x determined using 1138 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
267 parameters	Absolute structure parameter: −0.11 (17)
1 restraint

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	1.0825 (2)	0.2023 (3)	0.33409 (8)	0.0388 (5)
O2	1.2632 (2)	0.2265 (4)	0.25828 (10)	0.0661 (7)
C1	0.8685 (3)	0.4403 (4)	0.29484 (14)	0.0413 (7)
C2	0.9421 (3)	0.2698 (4)	0.28549 (13)	0.0359 (6)
C3	0.8814 (3)	0.1570 (4)	0.23162 (13)	0.0385 (7)
H3	0.9338	0.0395	0.2270	0.046*
C4	0.7432 (3)	0.2179 (4)	0.18449 (13)	0.0374 (6)
H4	0.7019	0.1416	0.1468	0.045*
C4A	0.6625 (3)	0.3879 (4)	0.19052 (12)	0.0319 (6)
C4B	0.5137 (3)	0.4506 (4)	0.13429 (12)	0.0330 (6)
C5	0.4014 (3)	0.2837 (4)	0.10522 (14)	0.0405 (7)
H5A	0.4730	0.2022	0.0812	0.049*
H5B	0.3675	0.2113	0.1426	0.049*
C6	0.2361 (4)	0.3401 (5)	0.05730 (15)	0.0462 (8)
H6A	0.2691	0.4028	0.0178	0.055*
H6B	0.1676	0.2279	0.0415	0.055*
C7	0.1239 (3)	0.4697 (4)	0.09132 (14)	0.0425 (7)
H7A	0.0835	0.4024	0.1285	0.051*
H7B	0.0188	0.5050	0.0587	0.051*
C8	0.2197 (3)	0.6458 (4)	0.11908 (13)	0.0390 (7)
C8A	0.3948 (3)	0.5887 (4)	0.16448 (12)	0.0334 (6)
H8A	0.3585	0.5209	0.2030	0.040*
C9	0.5059 (4)	0.7494 (4)	0.19617 (15)	0.0431 (7)
H9A	0.5673	0.8071	0.1623	0.052*
H9B	0.4290	0.8445	0.2113	0.052*
C10	0.6400 (4)	0.6854 (4)	0.25540 (15)	0.0470 (7)
H10A	0.5817	0.6768	0.2952	0.056*
H10B	0.7328	0.7810	0.2649	0.056*
C10A	0.7261 (3)	0.5000 (4)	0.24594 (13)	0.0379 (6)
C11	0.9377 (5)	0.5598 (5)	0.35593 (17)	0.0653 (11)
H11	0.8681	0.6774	0.3505	0.078*
C12	1.1296 (6)	0.6161 (8)	0.36183 (19)	0.0941 (16)
H12A	1.2045	0.5079	0.3745	0.141*
H12B	1.1568	0.7127	0.3961	0.141*
H12C	1.1508	0.6641	0.3186	0.141*
C13	0.9041 (5)	0.4715 (8)	0.42098 (18)	0.0814 (14)
H13A	0.7788	0.4440	0.4174	0.122*
H13B	0.9404	0.5574	0.4583	0.122*
H13C	0.9716	0.3562	0.4290	0.122*
C14	0.6051 (3)	0.5319 (5)	0.07852 (14)	0.0494 (8)
H14A	0.6672	0.6460	0.0947	0.074*
H14B	0.5170	0.5598	0.0390	0.074*
H14C	0.6892	0.4414	0.0666	0.074*
C15	0.2425 (4)	0.7775 (5)	0.06206 (17)	0.0540 (8)
H15A	0.2917	0.7092	0.0277	0.081*
H15B	0.3222	0.8783	0.0796	0.081*
H15C	0.1283	0.8293	0.0423	0.081*
C16	0.1036 (4)	0.7443 (6)	0.16232 (18)	0.0629 (10)
H16A	−0.0121	0.7680	0.1355	0.094*
H16B	0.1580	0.8622	0.1785	0.094*
H16C	0.0907	0.6655	0.2006	0.094*
C17	1.2417 (3)	0.1844 (4)	0.31324 (14)	0.0413 (7)
C18	1.3781 (3)	0.1078 (4)	0.36592 (13)	0.0366 (6)
C19	1.3442 (4)	0.0440 (5)	0.42702 (13)	0.0424 (7)
H19	1.2289	0.0526	0.4371	0.051*
C20	1.4771 (4)	−0.0320 (5)	0.47326 (15)	0.0546 (8)
H20	1.4535	−0.0762	0.5150	0.066*
C21	1.6455 (4)	−0.0433 (5)	0.45829 (16)	0.0532 (8)
H21	1.7372	−0.0958	0.4899	0.064*
C22	1.6800 (4)	0.0207 (5)	0.39825 (16)	0.0513 (8)
H22	1.7957	0.0133	0.3886	0.062*
C23	1.5477 (3)	0.0959 (5)	0.35175 (14)	0.0457 (7)
H23	1.5721	0.1395	0.3100	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0294 (9)	0.0476 (12)	0.0387 (9)	0.0043 (9)	0.0037 (7)	0.0049 (9)
O2	0.0380 (11)	0.110 (2)	0.0515 (13)	0.0043 (13)	0.0107 (9)	0.0304 (14)
C1	0.0373 (14)	0.0389 (17)	0.0442 (15)	0.0012 (13)	−0.0026 (12)	−0.0076 (13)
C2	0.0268 (12)	0.0423 (18)	0.0375 (14)	0.0014 (13)	0.0026 (10)	0.0028 (13)
C3	0.0338 (13)	0.0370 (17)	0.0453 (15)	0.0043 (13)	0.0085 (11)	−0.0029 (13)
C4	0.0334 (13)	0.0381 (17)	0.0406 (14)	0.0010 (13)	0.0064 (11)	−0.0082 (13)
C4A	0.0281 (13)	0.0335 (16)	0.0342 (14)	−0.0025 (11)	0.0059 (10)	−0.0010 (11)
C4B	0.0303 (13)	0.0361 (16)	0.0324 (12)	−0.0024 (12)	0.0047 (10)	0.0001 (12)
C5	0.0369 (14)	0.0390 (17)	0.0428 (15)	0.0014 (13)	−0.0008 (12)	−0.0081 (13)
C6	0.0404 (16)	0.0428 (19)	0.0500 (17)	−0.0026 (14)	−0.0078 (13)	−0.0094 (14)
C7	0.0303 (13)	0.0460 (18)	0.0491 (15)	−0.0025 (13)	0.0011 (11)	−0.0001 (14)
C8	0.0324 (13)	0.0398 (18)	0.0432 (14)	0.0010 (13)	0.0022 (11)	−0.0012 (13)
C8A	0.0324 (13)	0.0338 (16)	0.0336 (13)	0.0001 (12)	0.0049 (10)	−0.0004 (12)
C9	0.0420 (15)	0.0328 (17)	0.0509 (16)	0.0027 (13)	−0.0023 (12)	−0.0047 (13)
C10	0.0468 (16)	0.0366 (18)	0.0512 (16)	0.0047 (14)	−0.0100 (13)	−0.0096 (14)
C10A	0.0345 (13)	0.0347 (16)	0.0429 (15)	−0.0011 (12)	0.0018 (11)	−0.0053 (12)
C11	0.069 (2)	0.053 (2)	0.061 (2)	0.0181 (18)	−0.0263 (16)	−0.0213 (18)
C12	0.122 (4)	0.091 (3)	0.057 (2)	−0.063 (3)	−0.021 (2)	0.000 (2)
C13	0.056 (2)	0.129 (4)	0.060 (2)	−0.009 (2)	0.0117 (16)	−0.046 (3)
C14	0.0359 (14)	0.070 (2)	0.0441 (15)	0.0045 (16)	0.0121 (12)	0.0086 (16)
C15	0.0504 (17)	0.046 (2)	0.0610 (19)	0.0002 (15)	−0.0043 (14)	0.0134 (16)
C16	0.0399 (16)	0.076 (3)	0.071 (2)	0.0171 (18)	0.0046 (15)	−0.018 (2)
C17	0.0321 (13)	0.0477 (19)	0.0441 (16)	0.0019 (13)	0.0061 (11)	0.0081 (14)
C18	0.0345 (13)	0.0351 (16)	0.0391 (14)	−0.0002 (12)	0.0033 (11)	−0.0020 (12)
C19	0.0370 (14)	0.0466 (18)	0.0426 (15)	0.0003 (14)	0.0040 (12)	−0.0001 (14)
C20	0.0525 (18)	0.065 (2)	0.0442 (15)	0.0038 (17)	0.0011 (14)	0.0082 (16)
C21	0.0441 (16)	0.052 (2)	0.0562 (18)	0.0095 (16)	−0.0109 (14)	−0.0003 (16)
C22	0.0340 (15)	0.058 (2)	0.0602 (19)	0.0077 (15)	0.0039 (13)	−0.0046 (17)
C23	0.0344 (14)	0.055 (2)	0.0471 (15)	0.0033 (14)	0.0057 (12)	0.0011 (15)

Geometric parameters (Å, º) top

O1—C17	1.374 (3)	C10—C10A	1.520 (4)
O1—C2	1.422 (3)	C10—H10A	0.9900
O2—C17	1.192 (3)	C10—H10B	0.9900
C1—C2	1.381 (4)	C11—C12	1.524 (6)
C1—C10A	1.417 (4)	C11—C13	1.524 (6)
C1—C11	1.528 (4)	C11—H11	1.0000
C2—C3	1.377 (4)	C12—H12A	0.9800
C3—C4	1.378 (4)	C12—H12B	0.9800
C3—H3	0.9500	C12—H12C	0.9800
C4—C4A	1.390 (4)	C13—H13A	0.9800
C4—H4	0.9500	C13—H13B	0.9800
C4A—C10A	1.402 (4)	C13—H13C	0.9800
C4A—C4B	1.542 (3)	C14—H14A	0.9800
C4B—C5	1.540 (4)	C14—H14B	0.9800
C4B—C14	1.547 (4)	C14—H14C	0.9800
C4B—C8A	1.550 (4)	C15—H15A	0.9800
C5—C6	1.523 (4)	C15—H15B	0.9800
C5—H5A	0.9900	C15—H15C	0.9800
C5—H5B	0.9900	C16—H16A	0.9800
C6—C7	1.518 (4)	C16—H16B	0.9800
C6—H6A	0.9900	C16—H16C	0.9800
C6—H6B	0.9900	C17—C18	1.474 (4)
C7—C8	1.528 (4)	C18—C19	1.387 (4)
C7—H7A	0.9900	C18—C23	1.392 (4)
C7—H7B	0.9900	C19—C20	1.380 (4)
C8—C15	1.528 (4)	C19—H19	0.9500
C8—C16	1.531 (4)	C20—C21	1.390 (5)
C8—C8A	1.557 (4)	C20—H20	0.9500
C8A—C9	1.518 (4)	C21—C22	1.369 (5)
C8A—H8A	1.0000	C21—H21	0.9500
C9—C10	1.518 (4)	C22—C23	1.378 (4)
C9—H9A	0.9900	C22—H22	0.9500
C9—H9B	0.9900	C23—H23	0.9500

C17—O1—C2	116.01 (19)	C10A—C10—H10B	108.5
C2—C1—C10A	117.7 (2)	H10A—C10—H10B	107.5
C2—C1—C11	121.2 (3)	C4A—C10A—C1	120.6 (3)
C10A—C1—C11	121.2 (3)	C4A—C10A—C10	120.4 (2)
C3—C2—C1	122.8 (2)	C1—C10A—C10	119.0 (2)
C3—C2—O1	117.6 (2)	C12—C11—C13	110.5 (3)
C1—C2—O1	119.6 (2)	C12—C11—C1	114.6 (3)
C2—C3—C4	118.7 (3)	C13—C11—C1	112.1 (3)
C2—C3—H3	120.7	C12—C11—H11	106.3
C4—C3—H3	120.7	C13—C11—H11	106.3
C3—C4—C4A	121.8 (2)	C1—C11—H11	106.3
C3—C4—H4	119.1	C11—C12—H12A	109.5
C4A—C4—H4	119.1	C11—C12—H12B	109.5
C4—C4A—C10A	118.5 (2)	H12A—C12—H12B	109.5
C4—C4A—C4B	118.9 (2)	C11—C12—H12C	109.5
C10A—C4A—C4B	122.6 (2)	H12A—C12—H12C	109.5
C5—C4B—C4A	110.8 (2)	H12B—C12—H12C	109.5
C5—C4B—C14	108.4 (2)	C11—C13—H13A	109.5
C4A—C4B—C14	105.85 (19)	C11—C13—H13B	109.5
C5—C4B—C8A	108.6 (2)	H13A—C13—H13B	109.5
C4A—C4B—C8A	108.4 (2)	C11—C13—H13C	109.5
C14—C4B—C8A	114.9 (2)	H13A—C13—H13C	109.5
C6—C5—C4B	113.1 (2)	H13B—C13—H13C	109.5
C6—C5—H5A	109.0	C4B—C14—H14A	109.5
C4B—C5—H5A	109.0	C4B—C14—H14B	109.5
C6—C5—H5B	109.0	H14A—C14—H14B	109.5
C4B—C5—H5B	109.0	C4B—C14—H14C	109.5
H5A—C5—H5B	107.8	H14A—C14—H14C	109.5
C7—C6—C5	111.0 (2)	H14B—C14—H14C	109.5
C7—C6—H6A	109.4	C8—C15—H15A	109.5
C5—C6—H6A	109.4	C8—C15—H15B	109.5
C7—C6—H6B	109.4	H15A—C15—H15B	109.5
C5—C6—H6B	109.4	C8—C15—H15C	109.5
H6A—C6—H6B	108.0	H15A—C15—H15C	109.5
C6—C7—C8	113.5 (2)	H15B—C15—H15C	109.5
C6—C7—H7A	108.9	C8—C16—H16A	109.5
C8—C7—H7A	108.9	C8—C16—H16B	109.5
C6—C7—H7B	108.9	H16A—C16—H16B	109.5
C8—C7—H7B	108.9	C8—C16—H16C	109.5
H7A—C7—H7B	107.7	H16A—C16—H16C	109.5
C15—C8—C7	110.4 (2)	H16B—C16—H16C	109.5
C15—C8—C16	107.4 (3)	O2—C17—O1	122.5 (2)
C7—C8—C16	107.5 (2)	O2—C17—C18	125.0 (2)
C15—C8—C8A	114.1 (2)	O1—C17—C18	112.4 (2)
C7—C8—C8A	108.4 (2)	C19—C18—C23	119.5 (3)
C16—C8—C8A	108.7 (2)	C19—C18—C17	123.3 (2)
C9—C8A—C4B	109.0 (2)	C23—C18—C17	117.2 (2)
C9—C8A—C8	114.9 (2)	C20—C19—C18	120.3 (3)
C4B—C8A—C8	116.9 (2)	C20—C19—H19	119.9
C9—C8A—H8A	104.9	C18—C19—H19	119.9
C4B—C8A—H8A	104.9	C19—C20—C21	119.5 (3)
C8—C8A—H8A	104.9	C19—C20—H20	120.2
C10—C9—C8A	111.3 (3)	C21—C20—H20	120.2
C10—C9—H9A	109.4	C22—C21—C20	120.4 (3)
C8A—C9—H9A	109.4	C22—C21—H21	119.8
C10—C9—H9B	109.4	C20—C21—H21	119.8
C8A—C9—H9B	109.4	C21—C22—C23	120.3 (3)
H9A—C9—H9B	108.0	C21—C22—H22	119.8
C9—C10—C10A	115.0 (2)	C23—C22—H22	119.8
C9—C10—H10A	108.5	C22—C23—C18	120.0 (3)
C10A—C10—H10A	108.5	C22—C23—H23	120.0
C9—C10—H10B	108.5	C18—C23—H23	120.0

Experimental details

Crystal data
Chemical formula	C₂₇H₃₄O₂
M_r	390.54
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	180
a, b, c (Å)	7.7369 (3), 7.2079 (4), 20.2499 (9)
β (°)	99.816 (4)
V (Å³)	1112.74 (9)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.55
Crystal size (mm)	0.50 × 0.25 × 0.07

Data collection
Diffractometer	Agilent Xcalibur (Eos, Gemini ultra) diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.689, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	9197, 3116, 2926
R_int	0.033
θ_max (°)	60.8
(sin θ/λ)_max (Å⁻¹)	0.566

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.095, 1.04
No. of reflections	3116
No. of parameters	267
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.21
Absolute structure	Flack x determined using 1138 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Absolute structure parameter	−0.11 (17)

Computer programs: CrysAlis PRO (Agilent, 2012), SIR97 (Altomare et al., 1999), SHELXL2013 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012).

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Abingdon, England. Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Barrero, A. F., Quílez del Moral, J. F., Lucas, R., Payá, M., Akssira, M., Akaad, S. & Mellouki, F. (2003). J. Nat. Prod. 66, 844–50. Web of Science CrossRef PubMed CAS Google Scholar
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Volume 70| Part 8| August 2014| Pages o866-o867

doi:10.1107/S1600536814015827

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

(4bS,8aS)-1-Iso­propyl-4b,8,8-tri­methyl-4b,5,6,7,8,8a,9,10-octa­hydro­phenan­thren-2-yl benzoate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl benzoate