α-Costic anhydride.

THE TITLE COMPOUND [SYSTEMATIC NAME: 2-(4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octa-hydro-naphthalen-2-yl)acrylic acid anhydride], C(30)H(42)O(3), is a new isocostic anhydride which was synthesized from the aerial part of Inula Viscosa- (L) Aiton [or Dittrichia Viscosa- (L) Greuter]. The mol-ecule adopts an essentially linear shape with two terminal fused-rings bridged by the anhydride group. The external rings have the same conformation (half-chair) while each of the two inner rings has an almost ideal chair conformation. In the crystal, inter-molecular C-H⋯O inter-actions link the mol-ecules into a two-dimensional array in the bc plane.

Related literature

For background to the medicinal inter­est in Inula Viscosa­ (L) Aiton [or Dittrichia Viscosa­ (L) Greuter], see: Shtacher & Kasshman (1970 ▶); Bohlman & Gupta (1982 ▶); Azoulay et al. (1986 ▶); Bohlmann et al. (1977 ▶); Ceccherelli et al. (1988 ▶); Grande et al. (1985 ▶); Chiappini et al. (1982 ▶). For background to the phytochemical study of Moroccan plants, see: Tebaa et al. (2009 ▶); Zeroual et al. (2007 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C30H42O3

M = 450.64

Monoclinic,

a = 6.6699 (2) Å

b = 6.6335 (2) Å

c = 30.2948 (8) Å

β = 92.799 (1)°

V = 1338.79 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 298 K

0.28 × 0.17 × 0.12 mm

Data collection

Bruker X8 APEX CCD area-detector diffractometer

15300 measured reflections

2914 independent reflections

2604 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.109

S = 1.05

2914 reflections

304 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.12 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus; 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 DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810005064/tk2617sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005064/tk2617Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C30H42O3	F(000) = 492
Mr = 450.64	Dx = 1.118 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 15300 reflections
a = 6.6699 (2) Å	θ = 0.7–26.1°
b = 6.6335 (2) Å	µ = 0.07 mm−1
c = 30.2948 (8) Å	T = 298 K
β = 92.799 (1)°	Prism, colourless
V = 1338.79 (7) Å3	0.28 × 0.17 × 0.12 mm
Z = 2

Bruker X8 APEX CCD area-detector diffractometer	2604 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 26.1°, θmin = 0.7°
φ and ω scans	h = −8→8
15300 measured reflections	k = −8→8
2914 independent reflections	l = −37→37

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0425P)2 + 0.3687P] where P = (Fo2 + 2Fc2)/3
2914 reflections	(Δ/σ)max < 0.001
304 parameters	Δρmax = 0.17 e Å−3
1 restraint	Δρmin = −0.12 e Å−3

	x	y	z	Uiso*/Ueq
C1	−0.4278 (5)	0.3168 (6)	0.92476 (10)	0.0684 (9)
H1	−0.5086	0.2029	0.9263	0.087 (11)*
C2	−0.3866 (6)	0.4312 (7)	0.96587 (11)	0.0807 (12)
H2A	−0.3027	0.3501	0.9860	0.097*
H2B	−0.5123	0.4557	0.9798	0.097*
C3	−0.2841 (5)	0.6299 (7)	0.95871 (9)	0.0705 (9)
H3A	−0.2202	0.6748	0.9864	0.085*
H3B	−0.3840	0.7295	0.9495	0.085*
C4	−0.1256 (4)	0.6164 (5)	0.92373 (8)	0.0494 (6)
C5	−0.0308 (5)	0.8240 (5)	0.91750 (9)	0.0623 (8)
H5A	0.0449	0.8611	0.9444	0.075*
H5B	−0.1366	0.9229	0.9125	0.075*
C6	0.1087 (5)	0.8304 (5)	0.87881 (9)	0.0598 (8)
H6A	0.1571	0.9670	0.8751	0.072*
H6B	0.2238	0.7442	0.8853	0.072*
C7	0.0003 (4)	0.7606 (4)	0.83602 (8)	0.0423 (6)
H7	−0.1100	0.8554	0.8296	0.051*
C8	−0.0936 (4)	0.5527 (4)	0.84179 (8)	0.0450 (6)
H8A	0.0115	0.4537	0.8475	0.054*
H8B	−0.1682	0.5146	0.8148	0.054*
C9	−0.2345 (4)	0.5549 (4)	0.88021 (8)	0.0424 (6)
H9	−0.3318	0.6624	0.8733	0.051*
C10	−0.3577 (4)	0.3643 (5)	0.88525 (9)	0.0502 (7)
C11	−0.4056 (6)	0.2386 (6)	0.84572 (12)	0.0796 (10)
H11A	−0.4834	0.1240	0.8540	0.119*
H11B	−0.2833	0.1934	0.8335	0.119*
H11C	−0.4812	0.3168	0.8241	0.119*
C12	0.0350 (5)	0.4630 (7)	0.93871 (11)	0.0737 (10)
H12A	0.1411	0.4637	0.9184	0.111*
H12B	−0.0236	0.3309	0.9394	0.111*
H12C	0.0885	0.4980	0.9677	0.111*
C13	0.1364 (4)	0.7703 (4)	0.79758 (9)	0.0449 (6)
C14	0.2112 (6)	0.6149 (5)	0.77756 (12)	0.0845 (12)
H14A	0.2901	0.6342	0.7534	0.101*
H14B	0.1855	0.4851	0.7874	0.101*
C15	0.1767 (4)	0.9763 (4)	0.78202 (8)	0.0426 (6)
C16	0.3228 (3)	1.1350 (4)	0.72013 (8)	0.0415 (6)
C17	0.5257 (3)	1.1794 (4)	0.70471 (8)	0.0436 (6)
C18	0.6835 (4)	1.0992 (7)	0.72518 (11)	0.0753 (11)
H18A	0.6681	1.0147	0.7493	0.090*
H18B	0.8110	1.1266	0.7156	0.090*
C19	0.5274 (3)	1.3227 (4)	0.66603 (7)	0.0417 (6)
H19	0.4349	1.4330	0.6721	0.050*
C20	0.4477 (4)	1.2199 (6)	0.62350 (8)	0.0591 (8)
H20A	0.5305	1.1036	0.6176	0.071*
H20B	0.3119	1.1728	0.6273	0.071*
C21	0.4484 (4)	1.3633 (6)	0.58433 (8)	0.0630 (9)
H21A	0.3514	1.4696	0.5886	0.076*
H21B	0.4058	1.2903	0.5578	0.076*
C22	0.6533 (4)	1.4587 (5)	0.57758 (8)	0.0508 (7)
C23	0.7253 (4)	1.5623 (4)	0.62083 (8)	0.0415 (6)
H23	0.6203	1.6600	0.6272	0.050*
C24	0.7336 (4)	1.4171 (4)	0.65969 (8)	0.0447 (6)
H24A	0.7777	1.4886	0.6864	0.054*
H24B	0.8303	1.3115	0.6546	0.054*
C25	0.9128 (4)	1.6862 (5)	0.61507 (9)	0.0529 (7)
C26	0.9537 (5)	1.7582 (5)	0.57536 (11)	0.0681 (9)
H26	1.0674	1.8384	0.5736	0.074 (10)*
C27	0.8326 (6)	1.7205 (7)	0.53396 (11)	0.0801 (11)
H27A	0.9085	1.6354	0.5148	0.096*
H27B	0.8080	1.8477	0.5189	0.096*
C28	0.6343 (5)	1.6208 (7)	0.54171 (10)	0.0717 (9)
H28A	0.5824	1.5601	0.5144	0.086*
H28B	0.5391	1.7223	0.5503	0.086*
C29	1.0455 (5)	1.7295 (6)	0.65482 (12)	0.0789 (10)
H29A	1.1575	1.8094	0.6465	0.118*
H29B	1.0934	1.6050	0.6676	0.118*
H29C	0.9712	1.8020	0.6761	0.118*
C30	0.8016 (6)	1.2973 (6)	0.56362 (11)	0.0736 (10)
H30A	0.9330	1.3554	0.5624	0.110*
H30B	0.7596	1.2460	0.5350	0.110*
H30C	0.8052	1.1893	0.5847	0.110*
O1	0.3244 (3)	0.9824 (3)	0.75129 (6)	0.0519 (5)
O2	0.0998 (3)	1.1250 (3)	0.79450 (7)	0.0590 (5)
O3	0.1723 (3)	1.2153 (4)	0.70730 (6)	0.0600 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0541 (16)	0.078 (2)	0.074 (2)	−0.0201 (17)	0.0141 (14)	0.0170 (19)
C2	0.077 (2)	0.105 (3)	0.0628 (19)	−0.015 (2)	0.0278 (16)	0.017 (2)
C3	0.084 (2)	0.084 (2)	0.0460 (15)	−0.007 (2)	0.0241 (15)	−0.0028 (18)
C4	0.0552 (15)	0.0556 (16)	0.0378 (12)	−0.0088 (14)	0.0081 (10)	0.0062 (13)
C5	0.084 (2)	0.061 (2)	0.0425 (14)	−0.0198 (18)	0.0090 (13)	−0.0091 (14)
C6	0.0707 (18)	0.0589 (19)	0.0502 (15)	−0.0273 (16)	0.0081 (12)	−0.0005 (15)
C7	0.0535 (14)	0.0331 (13)	0.0411 (12)	−0.0028 (11)	0.0101 (10)	0.0045 (11)
C8	0.0552 (14)	0.0405 (14)	0.0399 (12)	−0.0079 (12)	0.0086 (10)	0.0021 (11)
C9	0.0423 (12)	0.0421 (14)	0.0433 (13)	0.0021 (11)	0.0086 (10)	0.0071 (11)
C10	0.0407 (13)	0.0517 (17)	0.0583 (15)	−0.0056 (12)	0.0031 (11)	0.0072 (14)
C11	0.079 (2)	0.072 (2)	0.089 (2)	−0.035 (2)	0.0108 (17)	−0.003 (2)
C12	0.0582 (17)	0.095 (3)	0.0669 (18)	−0.0035 (18)	−0.0069 (14)	0.032 (2)
C13	0.0557 (14)	0.0345 (13)	0.0458 (13)	−0.0037 (11)	0.0147 (11)	0.0045 (11)
C14	0.128 (3)	0.0383 (17)	0.093 (2)	−0.002 (2)	0.067 (2)	0.0088 (19)
C15	0.0462 (13)	0.0386 (14)	0.0435 (13)	−0.0029 (12)	0.0084 (10)	0.0055 (12)
C16	0.0401 (13)	0.0424 (14)	0.0428 (12)	−0.0048 (12)	0.0091 (10)	0.0047 (12)
C17	0.0383 (12)	0.0520 (16)	0.0411 (12)	−0.0035 (11)	0.0082 (9)	0.0067 (12)
C18	0.0452 (15)	0.105 (3)	0.0771 (19)	0.0025 (18)	0.0132 (13)	0.042 (2)
C19	0.0386 (11)	0.0476 (16)	0.0396 (12)	−0.0052 (12)	0.0074 (9)	0.0040 (12)
C20	0.0589 (16)	0.072 (2)	0.0471 (14)	−0.0277 (16)	0.0050 (12)	0.0014 (16)
C21	0.0638 (17)	0.086 (2)	0.0390 (13)	−0.0177 (18)	−0.0034 (11)	0.0025 (16)
C22	0.0540 (14)	0.0620 (18)	0.0371 (12)	−0.0056 (14)	0.0090 (10)	0.0056 (14)
C23	0.0428 (12)	0.0409 (14)	0.0418 (12)	0.0014 (11)	0.0114 (10)	0.0023 (11)
C24	0.0423 (12)	0.0508 (17)	0.0411 (12)	−0.0091 (12)	0.0025 (9)	0.0049 (12)
C25	0.0507 (14)	0.0443 (16)	0.0647 (16)	−0.0053 (13)	0.0124 (12)	0.0059 (14)
C26	0.0652 (18)	0.061 (2)	0.079 (2)	−0.0125 (17)	0.0203 (15)	0.0178 (18)
C27	0.095 (2)	0.083 (3)	0.0640 (19)	−0.007 (2)	0.0216 (17)	0.032 (2)
C28	0.078 (2)	0.087 (3)	0.0501 (16)	−0.004 (2)	0.0049 (14)	0.0217 (18)
C29	0.070 (2)	0.075 (3)	0.091 (2)	−0.032 (2)	0.0022 (17)	0.008 (2)
C30	0.094 (2)	0.066 (2)	0.0630 (19)	0.001 (2)	0.0318 (17)	−0.0088 (18)
O1	0.0483 (9)	0.0472 (11)	0.0620 (10)	0.0037 (9)	0.0215 (8)	0.0176 (10)
O2	0.0766 (13)	0.0362 (10)	0.0664 (12)	−0.0011 (10)	0.0270 (10)	0.0048 (10)
O3	0.0373 (9)	0.0784 (15)	0.0652 (11)	−0.0008 (10)	0.0099 (8)	0.0263 (12)

C1—C10	1.344 (4)	C16—O3	1.185 (3)
C1—C2	1.473 (5)	C16—O1	1.384 (3)
C1—H1	0.9300	C16—C17	1.482 (3)
C2—C3	1.506 (6)	C17—C18	1.308 (4)
C2—H2A	0.9700	C17—C19	1.509 (3)
C2—H2B	0.9700	C18—H18A	0.9300
C3—C4	1.535 (3)	C18—H18B	0.9300
C3—H3A	0.9700	C19—C20	1.530 (4)
C3—H3B	0.9700	C19—C24	1.532 (3)
C4—C9	1.529 (4)	C19—H19	0.9800
C4—C12	1.531 (5)	C20—C21	1.521 (4)
C4—C5	1.531 (4)	C20—H20A	0.9700
C5—C6	1.532 (4)	C20—H20B	0.9700
C5—H5A	0.9700	C21—C22	1.529 (4)
C5—H5B	0.9700	C21—H21A	0.9700
C6—C7	1.525 (4)	C21—H21B	0.9700
C6—H6A	0.9700	C22—C28	1.530 (4)
C6—H6B	0.9700	C22—C30	1.531 (4)
C7—C13	1.512 (3)	C22—C23	1.536 (4)
C7—C8	1.528 (4)	C23—C25	1.514 (4)
C7—H7	0.9800	C23—C24	1.520 (3)
C8—C9	1.531 (3)	C23—H23	0.9800
C8—H8A	0.9700	C24—H24A	0.9700
C8—H8B	0.9700	C24—H24B	0.9700
C9—C10	1.520 (4)	C25—C26	1.335 (4)
C9—H9	0.9800	C25—C29	1.487 (4)
C10—C11	1.481 (5)	C26—C27	1.479 (5)
C11—H11A	0.9600	C26—H26	0.9300
C11—H11B	0.9600	C27—C28	1.507 (5)
C11—H11C	0.9600	C27—H27A	0.9700
C12—H12A	0.9600	C27—H27B	0.9700
C12—H12B	0.9600	C28—H28A	0.9700
C12—H12C	0.9600	C28—H28B	0.9700
C13—C14	1.307 (4)	C29—H29A	0.9600
C13—C15	1.475 (4)	C29—H29B	0.9600
C14—H14A	0.9300	C29—H29C	0.9600
C14—H14B	0.9300	C30—H30A	0.9600
C15—O2	1.182 (3)	C30—H30B	0.9600
C15—O1	1.389 (3)	C30—H30C	0.9600
C10—C1—C2	125.0 (3)	O3—C16—C17	125.3 (2)
C10—C1—H1	117.5	O1—C16—C17	112.6 (2)
C2—C1—H1	117.5	C18—C17—C16	119.7 (2)
C1—C2—C3	113.4 (3)	C18—C17—C19	126.0 (2)
C1—C2—H2A	108.9	C16—C17—C19	114.3 (2)
C3—C2—H2A	108.9	C17—C18—H18A	120.0
C1—C2—H2B	108.9	C17—C18—H18B	120.0
C3—C2—H2B	108.9	H18A—C18—H18B	120.0
H2A—C2—H2B	107.7	C17—C19—C20	111.0 (2)
C2—C3—C4	112.4 (3)	C17—C19—C24	113.3 (2)
C2—C3—H3A	109.1	C20—C19—C24	110.71 (19)
C4—C3—H3A	109.1	C17—C19—H19	107.2
C2—C3—H3B	109.1	C20—C19—H19	107.2
C4—C3—H3B	109.1	C24—C19—H19	107.2
H3A—C3—H3B	107.9	C21—C20—C19	111.3 (3)
C9—C4—C12	112.0 (3)	C21—C20—H20A	109.4
C9—C4—C5	108.4 (2)	C19—C20—H20A	109.4
C12—C4—C5	110.3 (3)	C21—C20—H20B	109.4
C9—C4—C3	107.3 (2)	C19—C20—H20B	109.4
C12—C4—C3	109.2 (3)	H20A—C20—H20B	108.0
C5—C4—C3	109.6 (3)	C20—C21—C22	113.6 (2)
C4—C5—C6	112.9 (3)	C20—C21—H21A	108.9
C4—C5—H5A	109.0	C22—C21—H21A	108.9
C6—C5—H5A	109.0	C20—C21—H21B	108.9
C4—C5—H5B	109.0	C22—C21—H21B	108.9
C6—C5—H5B	109.0	H21A—C21—H21B	107.7
H5A—C5—H5B	107.8	C21—C22—C28	110.0 (2)
C7—C6—C5	111.2 (2)	C21—C22—C30	109.9 (3)
C7—C6—H6A	109.4	C28—C22—C30	109.1 (2)
C5—C6—H6A	109.4	C21—C22—C23	108.4 (2)
C7—C6—H6B	109.4	C28—C22—C23	107.7 (3)
C5—C6—H6B	109.4	C30—C22—C23	111.7 (2)
H6A—C6—H6B	108.0	C25—C23—C24	115.7 (2)
C13—C7—C6	111.4 (2)	C25—C23—C22	111.7 (2)
C13—C7—C8	113.0 (2)	C24—C23—C22	112.0 (2)
C6—C7—C8	110.9 (2)	C25—C23—H23	105.4
C13—C7—H7	107.1	C24—C23—H23	105.4
C6—C7—H7	107.1	C22—C23—H23	105.4
C8—C7—H7	107.1	C23—C24—C19	110.9 (2)
C7—C8—C9	110.4 (2)	C23—C24—H24A	109.5
C7—C8—H8A	109.6	C19—C24—H24A	109.5
C9—C8—H8A	109.6	C23—C24—H24B	109.5
C7—C8—H8B	109.6	C19—C24—H24B	109.5
C9—C8—H8B	109.6	H24A—C24—H24B	108.0
H8A—C8—H8B	108.1	C26—C25—C29	121.4 (3)
C10—C9—C4	111.8 (2)	C26—C25—C23	120.3 (3)
C10—C9—C8	115.1 (2)	C29—C25—C23	118.3 (2)
C4—C9—C8	112.0 (2)	C25—C26—C27	125.2 (3)
C10—C9—H9	105.7	C25—C26—H26	117.4
C4—C9—H9	105.7	C27—C26—H26	117.4
C8—C9—H9	105.7	C26—C27—C28	112.9 (3)
C1—C10—C11	121.2 (3)	C26—C27—H27A	109.0
C1—C10—C9	119.9 (3)	C28—C27—H27A	109.0
C11—C10—C9	118.9 (2)	C26—C27—H27B	109.0
C10—C11—H11A	109.5	C28—C27—H27B	109.0
C10—C11—H11B	109.5	H27A—C27—H27B	107.8
H11A—C11—H11B	109.5	C27—C28—C22	112.1 (3)
C10—C11—H11C	109.5	C27—C28—H28A	109.2
H11A—C11—H11C	109.5	C22—C28—H28A	109.2
H11B—C11—H11C	109.5	C27—C28—H28B	109.2
C4—C12—H12A	109.5	C22—C28—H28B	109.2
C4—C12—H12B	109.5	H28A—C28—H28B	107.9
H12A—C12—H12B	109.5	C25—C29—H29A	109.5
C4—C12—H12C	109.5	C25—C29—H29B	109.5
H12A—C12—H12C	109.5	H29A—C29—H29B	109.5
H12B—C12—H12C	109.5	C25—C29—H29C	109.5
C14—C13—C15	120.2 (2)	H29A—C29—H29C	109.5
C14—C13—C7	125.5 (3)	H29B—C29—H29C	109.5
C15—C13—C7	114.3 (2)	C22—C30—H30A	109.5
C13—C14—H14A	120.0	C22—C30—H30B	109.5
C13—C14—H14B	120.0	H30A—C30—H30B	109.5
H14A—C14—H14B	120.0	C22—C30—H30C	109.5
O2—C15—O1	121.6 (2)	H30A—C30—H30C	109.5
O2—C15—C13	125.6 (2)	H30B—C30—H30C	109.5
O1—C15—C13	112.8 (2)	C16—O1—C15	119.8 (2)
O3—C16—O1	122.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O2i	0.93	2.47	3.378 (4)	166
C18—H18B···O3ii	0.93	2.51	3.419 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O2i	0.93	2.47	3.378 (4)	166
C18—H18B⋯O3ii	0.93	2.51	3.419 (3)	168

Symmetry codes: (i) ; (ii) .