14-Angeloyloxycacalohastine from Psacalium peltatum.

THE TITLE COMPOUND [SYSTEMATIC NAME: (9-meth-oxy-3,5-dimethyl-5,6-dihydro-naphtho-[2,3-b]furan-4-yl)methyl 2-meth-yl-but-2-enoate], C(21)H(24)O(4), was isolated from matarique, or Psacalium peltatum (Kunth). The structure is almost planar. The angelo-yloxy group makes an angle of 62.08 (2)° with the furan-oeremophilane skeleton. The carbonyl O atom is disordered between two positions with a 76:24 ratio. The mol-ecules in the crystal are joined by very weak C-H-O inter-actions in the ac plane.

Related literature

For fundamental background information, see: Romo de Vivar et al. (2007 ▶). For biological activity, see: Acevedo-Quiroz et al. (2008 ▶); Alarcón-Aguilar et al. (2000 ▶); Bye et al. (1995 ▶); Contreras-Weber et al. (2002 ▶); Jimenez-Estrada et al. (2006 ▶). For compound isolation, see: Abdo et al. (1992 ▶); Bohlmann et al. (1977 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H24O4

M = 340.40

Orthorhombic,

a = 7.1627 (17) Å

b = 10.276 (2) Å

c = 24.605 (6) Å

V = 1811.1 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.40 × 0.40 × 0.40 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

20061 measured reflections

1945 independent reflections

1701 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.095

S = 1.12

1945 reflections

241 parameters

21 restraints

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812004199/aa2037sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004199/aa2037Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004199/aa2037Isup3.cml

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

C21H24O4	F(000) = 728
Mr = 340.40	Dx = 1.248 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9953 reflections
a = 7.1627 (17) Å	θ = 2.6–25.1°
b = 10.276 (2) Å	µ = 0.09 mm−1
c = 24.605 (6) Å	T = 298 K
V = 1811.1 (7) Å3	Prism, colourless
Z = 4	0.40 × 0.40 × 0.40 mm

Bruker SMART APEX CCD area-detector diffractometer	1701 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 25.4°, θmin = 2.2°
Detector resolution: 0.83 pixels mm-1	h = −8→8
ω scans	k = −12→12
20061 measured reflections	l = −29→29
1945 independent reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0598P)2] where P = (Fo2 + 2Fc2)/3
1945 reflections	(Δ/σ)max = 0.001
241 parameters	Δρmax = 0.15 e Å−3
21 restraints	Δρmin = −0.15 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.2416 (2)	0.31693 (16)	0.75432 (6)	0.0714 (5)
O2	−0.0374 (2)	0.52184 (18)	0.78161 (7)	0.0781 (5)
O3	0.6537 (2)	0.35107 (13)	0.92670 (5)	0.0575 (4)
C2	0.4000 (4)	0.2430 (2)	0.75866 (9)	0.0744 (7)
H2	0.4239	0.1717	0.7364	0.089*
C3	0.5167 (3)	0.2821 (2)	0.79734 (9)	0.0609 (6)
C4	0.4777 (3)	0.48417 (18)	0.86340 (7)	0.0474 (5)
C5	0.3937 (4)	0.6883 (2)	0.91708 (8)	0.0600 (6)
H5	0.4798	0.6518	0.9440	0.072*
C6	0.2181 (4)	0.7334 (2)	0.94676 (10)	0.0741 (7)
H6A	0.1798	0.6668	0.9723	0.089*
H6B	0.2463	0.8117	0.9672	0.089*
C7	0.0626 (4)	0.7604 (2)	0.90877 (11)	0.0724 (7)
H7	−0.0248	0.8239	0.9176	0.087*
C8	0.0457 (3)	0.6957 (2)	0.86251 (10)	0.0618 (6)
H8	−0.0526	0.7154	0.8392	0.074*
C9	0.1341 (3)	0.5079 (2)	0.80519 (8)	0.0529 (5)
C10	0.2624 (3)	0.4122 (2)	0.79325 (7)	0.0521 (5)
C11	0.4302 (3)	0.39708 (18)	0.82102 (7)	0.0487 (5)
C12	0.3504 (3)	0.58296 (18)	0.87563 (7)	0.0464 (5)
C13	0.1786 (3)	0.59388 (19)	0.84724 (7)	0.0500 (5)
C14	0.6933 (4)	0.2148 (3)	0.81219 (10)	0.0830 (8)
H14A	0.7065	0.1375	0.7907	0.124*
H14B	0.6903	0.1919	0.8500	0.124*
H14C	0.7971	0.2717	0.8055	0.124*
C15	0.6592 (3)	0.4671 (2)	0.89264 (8)	0.0561 (5)
H15A	0.7597	0.4593	0.8664	0.067*
H15B	0.6836	0.5429	0.9150	0.067*
C16	0.4913 (4)	0.8027 (2)	0.88907 (12)	0.0783 (8)
H16A	0.4144	0.8343	0.8600	0.117*
H16B	0.6091	0.7743	0.8747	0.117*
H16C	0.5116	0.8712	0.9150	0.117*
C17	0.6327 (3)	0.3665 (2)	0.97976 (9)	0.0557 (5)
O4	0.5953 (19)	0.4714 (3)	0.99988 (18)	0.074 (2)	0.76 (3)
O4A	0.697 (5)	0.4664 (12)	0.9991 (6)	0.071 (4)	0.24 (3)
C18	0.6328 (3)	0.2407 (2)	1.00916 (8)	0.0562 (5)
C19	0.6373 (3)	0.2364 (2)	1.06292 (10)	0.0677 (6)
H19	0.6366	0.1532	1.0778	0.081*
C20	0.6433 (5)	0.3438 (3)	1.10315 (9)	0.0836 (8)
H20A	0.5185	0.3719	1.1111	0.125*
H20B	0.7133	0.4153	1.0885	0.125*
H20C	0.7021	0.3138	1.1359	0.125*
C21	0.6300 (4)	0.1180 (2)	0.97545 (11)	0.0767 (7)
H21A	0.6139	0.0440	0.9988	0.115*
H21B	0.7457	0.1099	0.9561	0.115*
H21C	0.5285	0.1219	0.9500	0.115*
C22	−0.0716 (4)	0.4709 (3)	0.72916 (10)	0.0860 (8)
H22A	−0.0871	0.3783	0.7314	0.129*
H22B	0.0322	0.4906	0.7059	0.129*
H22C	−0.1830	0.5093	0.7146	0.129*

	U11	U22	U33	U12	U13	U23
O1	0.0921 (12)	0.0633 (10)	0.0588 (9)	0.0009 (10)	−0.0122 (9)	−0.0173 (8)
O2	0.0667 (10)	0.0908 (12)	0.0767 (11)	0.0047 (10)	−0.0186 (9)	−0.0119 (10)
O3	0.0778 (9)	0.0467 (7)	0.0479 (7)	0.0093 (8)	−0.0067 (8)	0.0009 (6)
C2	0.111 (2)	0.0586 (14)	0.0541 (13)	0.0083 (16)	0.0060 (14)	−0.0168 (11)
C3	0.0824 (15)	0.0526 (12)	0.0477 (11)	0.0086 (12)	0.0124 (11)	−0.0027 (10)
C4	0.0607 (12)	0.0424 (10)	0.0390 (10)	−0.0013 (10)	0.0045 (9)	0.0044 (8)
C5	0.0849 (16)	0.0449 (11)	0.0501 (11)	0.0098 (12)	−0.0100 (11)	−0.0052 (9)
C6	0.115 (2)	0.0514 (13)	0.0554 (12)	0.0123 (14)	0.0105 (13)	−0.0075 (11)
C7	0.0786 (16)	0.0509 (13)	0.0878 (18)	0.0144 (14)	0.0141 (14)	−0.0071 (13)
C8	0.0660 (14)	0.0470 (11)	0.0724 (14)	0.0065 (12)	0.0023 (12)	0.0059 (11)
C9	0.0608 (12)	0.0493 (11)	0.0486 (10)	−0.0041 (11)	−0.0022 (10)	0.0068 (9)
C10	0.0702 (13)	0.0453 (11)	0.0407 (9)	−0.0046 (11)	0.0000 (10)	−0.0025 (9)
C11	0.0669 (12)	0.0402 (10)	0.0389 (9)	0.0001 (10)	0.0074 (9)	0.0027 (8)
C12	0.0636 (12)	0.0372 (9)	0.0385 (9)	−0.0001 (10)	0.0013 (9)	0.0035 (8)
C13	0.0648 (12)	0.0396 (10)	0.0455 (10)	−0.0014 (10)	0.0036 (10)	0.0069 (8)
C14	0.101 (2)	0.0752 (17)	0.0732 (16)	0.0340 (16)	0.0106 (15)	−0.0099 (13)
C15	0.0649 (12)	0.0520 (12)	0.0514 (11)	0.0023 (12)	0.0032 (10)	0.0045 (10)
C16	0.0901 (18)	0.0530 (13)	0.0918 (18)	−0.0111 (14)	−0.0088 (15)	−0.0155 (13)
C17	0.0678 (13)	0.0483 (12)	0.0509 (11)	0.0002 (11)	−0.0043 (11)	−0.0024 (9)
O4	0.123 (6)	0.0456 (13)	0.0548 (15)	0.0098 (19)	0.006 (2)	−0.0040 (11)
O4A	0.105 (11)	0.050 (4)	0.059 (5)	0.003 (6)	−0.020 (6)	−0.009 (4)
C18	0.0589 (13)	0.0493 (11)	0.0603 (13)	0.0018 (11)	−0.0077 (10)	0.0068 (10)
C19	0.0669 (14)	0.0678 (14)	0.0685 (14)	0.0039 (13)	−0.0034 (12)	0.0160 (12)
C20	0.099 (2)	0.0994 (19)	0.0529 (13)	0.0107 (19)	−0.0019 (14)	0.0008 (13)
C21	0.0969 (19)	0.0458 (13)	0.0873 (16)	0.0053 (13)	−0.0173 (16)	0.0029 (12)
C22	0.0881 (18)	0.105 (2)	0.0646 (14)	−0.0133 (19)	−0.0220 (14)	0.0098 (14)

O1—C2	1.370 (3)	C10—C11	1.392 (3)
O1—C10	1.378 (2)	C12—C13	1.420 (3)
O2—C9	1.366 (3)	C14—H14A	0.9600
O2—C22	1.414 (3)	C14—H14B	0.9600
O3—C17	1.324 (2)	C14—H14C	0.9600
O3—C15	1.458 (2)	C15—H15A	0.9700
C2—C3	1.329 (3)	C15—H15B	0.9700
C2—H2	0.9300	C16—H16A	0.9600
C3—C11	1.456 (3)	C16—H16B	0.9600
C3—C14	1.487 (4)	C16—H16C	0.9600
C4—C12	1.397 (3)	C17—O4	1.216 (3)
C4—C11	1.415 (3)	C17—O4A	1.221 (8)
C4—C15	1.497 (3)	C17—C18	1.481 (3)
C5—C12	1.519 (3)	C18—C19	1.324 (3)
C5—C6	1.527 (4)	C18—C21	1.510 (3)
C5—C16	1.532 (4)	C19—C20	1.483 (4)
C5—H5	0.9800	C19—H19	0.9300
C6—C7	1.480 (4)	C20—H20A	0.9600
C6—H6A	0.9700	C20—H20B	0.9600
C6—H6B	0.9700	C20—H20C	0.9600
C7—C8	1.324 (3)	C21—H21A	0.9600
C7—H7	0.9300	C21—H21B	0.9600
C8—C13	1.463 (3)	C21—H21C	0.9600
C8—H8	0.9300	C22—H22A	0.9600
C9—C10	1.377 (3)	C22—H22B	0.9600
C9—C13	1.397 (3)	C22—H22C	0.9600
C2—O1—C10	104.50 (17)	C3—C14—H14B	109.5
C9—O2—C22	120.3 (2)	H14A—C14—H14B	109.5
C17—O3—C15	118.19 (16)	C3—C14—H14C	109.5
C3—C2—O1	114.2 (2)	H14A—C14—H14C	109.5
C3—C2—H2	122.9	H14B—C14—H14C	109.5
O1—C2—H2	122.9	O3—C15—C4	110.43 (18)
C2—C3—C11	105.3 (2)	O3—C15—H15A	109.6
C2—C3—C14	124.8 (2)	C4—C15—H15A	109.6
C11—C3—C14	129.9 (2)	O3—C15—H15B	109.6
C12—C4—C11	117.49 (19)	C4—C15—H15B	109.6
C12—C4—C15	123.27 (18)	H15A—C15—H15B	108.1
C11—C4—C15	119.24 (19)	C5—C16—H16A	109.5
C12—C5—C6	111.7 (2)	C5—C16—H16B	109.5
C12—C5—C16	109.76 (18)	H16A—C16—H16B	109.5
C6—C5—C16	111.0 (2)	C5—C16—H16C	109.5
C12—C5—H5	108.1	H16A—C16—H16C	109.5
C6—C5—H5	108.1	H16B—C16—H16C	109.5
C16—C5—H5	108.1	O4—C17—O3	122.2 (3)
C7—C6—C5	112.01 (19)	O4A—C17—O3	116.2 (10)
C7—C6—H6A	109.2	O4—C17—C18	125.1 (3)
C5—C6—H6A	109.2	O4A—C17—C18	122.9 (6)
C7—C6—H6B	109.2	O3—C17—C18	112.17 (19)
C5—C6—H6B	109.2	C19—C18—C17	121.1 (2)
H6A—C6—H6B	107.9	C19—C18—C21	121.5 (2)
C8—C7—C6	121.2 (2)	C17—C18—C21	117.43 (18)
C8—C7—H7	119.4	C18—C19—C20	130.0 (2)
C6—C7—H7	119.4	C18—C19—H19	115.0
C7—C8—C13	121.4 (2)	C20—C19—H19	115.0
C7—C8—H8	119.3	C19—C20—H20A	109.5
C13—C8—H8	119.3	C19—C20—H20B	109.5
O2—C9—C10	125.7 (2)	H20A—C20—H20B	109.5
O2—C9—C13	116.9 (2)	C19—C20—H20C	109.5
C10—C9—C13	117.22 (19)	H20A—C20—H20C	109.5
O1—C10—C9	125.70 (19)	H20B—C20—H20C	109.5
O1—C10—C11	110.82 (18)	C18—C21—H21A	109.5
C9—C10—C11	123.45 (19)	C18—C21—H21B	109.5
C10—C11—C4	119.90 (19)	H21A—C21—H21B	109.5
C10—C11—C3	105.17 (19)	C18—C21—H21C	109.5
C4—C11—C3	134.9 (2)	H21A—C21—H21C	109.5
C4—C12—C13	121.13 (17)	H21B—C21—H21C	109.5
C4—C12—C5	121.96 (19)	O2—C22—H22A	109.5
C13—C12—C5	116.80 (18)	O2—C22—H22B	109.5
C9—C13—C12	120.79 (19)	H22A—C22—H22B	109.5
C9—C13—C8	119.6 (2)	O2—C22—H22C	109.5
C12—C13—C8	119.60 (18)	H22A—C22—H22C	109.5
C3—C14—H14A	109.5	H22B—C22—H22C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2i	0.97	2.62	3.536 (3)	157
C6—H6B···O4ii	0.97	2.61	3.42	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O2i	0.97	2.62	3.536 (3)	157
C6—H6B⋯O4ii	0.97	2.61	3.42 (2)	142

Symmetry codes: (i) ; (ii) .