Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802002982/cv6091sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802002982/cv6091Isup2.hkl |
CCDC reference: 182636
The plants of Achillea vermacularis (Compositae) were collected from Tehran area in July, 1997, shade-dried and ground whole plant material (6 kg) was extracted with methanol. The resulting gummy material (600 g) was partitioned into hexane, ethyl acetate and n-butanol soluble fractions. The ethyl acetate fraction was subjected to column chromatography using hexane/ethyl acetate (7:3) over flash silica which gel afforded (I) as colorless needles suitable XRD analysis.
The H atoms were located from difference Fourier synthesis and were included in the refinement at geometrically idealized positions, with C—H distances in the range 0.95–1.00 Å, utilizing riding models and allowing isotropic displacement parameters 1.2 (non-methyl) and 1.5 (methyl) times the equivalent isotropic displacement parameters of the atoms to which they were bonded.
Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN (Molecular Structure Corporation, 1994); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. ORTEPII (Johnson, 1976) drawing of (I) with displacement ellipsoids plotted at the 50% probability level. |
C17H20O5 | F(000) = 324 |
Mr = 304.33 | Dx = 1.266 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71069 Å |
a = 10.2083 (2) Å | Cell parameters from 2454 reflections |
b = 7.5434 (2) Å | θ = 1.0–30.0° |
c = 11.0118 (3) Å | µ = 0.09 mm−1 |
β = 109.677 (1)° | T = 173 K |
V = 798.45 (3) Å3 | Block, colourless |
Z = 2 | 0.25 × 0.20 × 0.18 mm |
Nonius KappaCCD diffractometer | 2477 independent reflections |
Radiation source: fine-focus sealed tube | 2297 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ω–2ϕ scans | θmax = 30.0°, θmin = 3.3° |
Absorption correction: multi-scan (SORTAV: Blessing, 1995, 1997) | h = −14→14 |
Tmin = 0.977, Tmax = 0.983 | k = −10→10 |
4575 measured reflections | l = −15→15 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.047P)2 + 0.087P] where P = (Fo2 + 2Fc2)/3 |
2477 reflections | (Δ/σ)max = 0.003 |
203 parameters | Δρmax = 0.21 e Å−3 |
1 restraint | Δρmin = −0.13 e Å−3 |
C17H20O5 | V = 798.45 (3) Å3 |
Mr = 304.33 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 10.2083 (2) Å | µ = 0.09 mm−1 |
b = 7.5434 (2) Å | T = 173 K |
c = 11.0118 (3) Å | 0.25 × 0.20 × 0.18 mm |
β = 109.677 (1)° |
Nonius KappaCCD diffractometer | 2477 independent reflections |
Absorption correction: multi-scan (SORTAV: Blessing, 1995, 1997) | 2297 reflections with I > 2σ(I) |
Tmin = 0.977, Tmax = 0.983 | Rint = 0.016 |
4575 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 1 restraint |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.21 e Å−3 |
2477 reflections | Δρmin = −0.13 e Å−3 |
203 parameters |
x | y | z | Uiso*/Ueq | ||
O1 | 0.40145 (13) | 0.18569 (18) | 0.29681 (10) | 0.0416 (3) | |
O2 | 0.41064 (11) | 0.28261 (18) | 0.81551 (11) | 0.0385 (3) | |
O3 | 0.44291 (15) | 0.3757 (3) | 1.01584 (15) | 0.0709 (6) | |
O4 | 0.88610 (10) | 0.22105 (17) | 0.88429 (10) | 0.0357 (3) | |
O5 | 0.99662 (14) | 0.3945 (3) | 0.78545 (16) | 0.0650 (5) | |
C1 | 0.50669 (15) | 0.1324 (2) | 0.52925 (13) | 0.0286 (3) | |
C2 | 0.39214 (16) | 0.1641 (2) | 0.40408 (14) | 0.0321 (3) | |
C3 | 0.26168 (15) | 0.1607 (2) | 0.43196 (15) | 0.0346 (3) | |
H3 | 0.1722 | 0.1748 | 0.3687 | 0.042* | |
C4 | 0.28403 (15) | 0.1353 (2) | 0.55720 (15) | 0.0323 (3) | |
C5 | 0.43934 (14) | 0.1164 (2) | 0.63346 (13) | 0.0278 (3) | |
H5 | 0.4585 | −0.0035 | 0.6744 | 0.033* | |
C6 | 0.49748 (14) | 0.2601 (2) | 0.73539 (14) | 0.0289 (3) | |
H6 | 0.5011 | 0.3748 | 0.6911 | 0.035* | |
C7 | 0.64121 (14) | 0.2215 (2) | 0.83319 (13) | 0.0294 (3) | |
H7 | 0.6421 | 0.0969 | 0.8645 | 0.035* | |
C8 | 0.75700 (14) | 0.2416 (2) | 0.77678 (14) | 0.0295 (3) | |
H8 | 0.7528 | 0.3610 | 0.7362 | 0.035* | |
C9 | 0.75161 (15) | 0.0953 (2) | 0.67924 (15) | 0.0330 (3) | |
H9A | 0.8443 | 0.0850 | 0.6697 | 0.040* | |
H9B | 0.7312 | −0.0188 | 0.7136 | 0.040* | |
C10 | 0.64389 (15) | 0.1263 (2) | 0.54739 (14) | 0.0307 (3) | |
C11 | 0.64252 (17) | 0.3477 (3) | 0.94242 (16) | 0.0416 (4) | |
H11 | 0.6641 | 0.4702 | 0.9201 | 0.050* | |
C12 | 0.49165 (19) | 0.3396 (3) | 0.93434 (18) | 0.0464 (4) | |
C13 | 0.7393 (2) | 0.3019 (5) | 1.07851 (18) | 0.0672 (8) | |
H13A | 0.7124 | 0.3708 | 1.1418 | 0.101* | |
H13B | 0.8355 | 0.3304 | 1.0863 | 0.101* | |
H13C | 0.7320 | 0.1751 | 1.0945 | 0.101* | |
C14 | 0.70502 (18) | 0.1503 (3) | 0.44187 (16) | 0.0383 (4) | |
H14A | 0.6306 | 0.1782 | 0.3609 | 0.058* | |
H14B | 0.7517 | 0.0407 | 0.4315 | 0.058* | |
H14C | 0.7725 | 0.2476 | 0.4645 | 0.058* | |
C15 | 0.17222 (15) | 0.1207 (3) | 0.61644 (18) | 0.0434 (4) | |
H15A | 0.0816 | 0.1087 | 0.5482 | 0.065* | |
H15B | 0.1724 | 0.2274 | 0.6673 | 0.065* | |
H15C | 0.1895 | 0.0163 | 0.6727 | 0.065* | |
C16 | 0.99833 (16) | 0.3077 (3) | 0.87667 (18) | 0.0396 (4) | |
C17 | 1.12117 (17) | 0.2786 (4) | 0.9959 (2) | 0.0574 (6) | |
H17A | 1.2070 | 0.2955 | 0.9761 | 0.086* | |
H17B | 1.1186 | 0.1577 | 1.0275 | 0.086* | |
H17C | 1.1184 | 0.3636 | 1.0623 | 0.086* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0498 (6) | 0.0426 (7) | 0.0316 (5) | 0.0048 (6) | 0.0126 (5) | 0.0008 (5) |
O2 | 0.0291 (5) | 0.0470 (7) | 0.0441 (6) | −0.0036 (5) | 0.0184 (4) | −0.0123 (5) |
O3 | 0.0523 (8) | 0.1082 (16) | 0.0624 (9) | −0.0121 (10) | 0.0326 (7) | −0.0406 (11) |
O4 | 0.0247 (5) | 0.0387 (6) | 0.0395 (6) | −0.0043 (4) | 0.0055 (4) | −0.0007 (5) |
O5 | 0.0366 (7) | 0.0782 (12) | 0.0800 (10) | −0.0109 (8) | 0.0195 (7) | 0.0200 (10) |
C1 | 0.0302 (6) | 0.0254 (6) | 0.0301 (6) | 0.0004 (6) | 0.0098 (5) | −0.0011 (6) |
C2 | 0.0370 (7) | 0.0251 (7) | 0.0324 (7) | 0.0016 (6) | 0.0093 (5) | −0.0013 (6) |
C3 | 0.0303 (7) | 0.0320 (8) | 0.0362 (7) | 0.0014 (6) | 0.0043 (5) | 0.0012 (6) |
C4 | 0.0270 (7) | 0.0282 (7) | 0.0396 (7) | −0.0017 (6) | 0.0084 (5) | −0.0004 (6) |
C5 | 0.0258 (6) | 0.0260 (7) | 0.0310 (6) | −0.0016 (5) | 0.0089 (5) | −0.0006 (5) |
C6 | 0.0256 (6) | 0.0295 (7) | 0.0335 (7) | −0.0014 (6) | 0.0125 (5) | −0.0030 (6) |
C7 | 0.0259 (6) | 0.0315 (7) | 0.0306 (6) | −0.0041 (6) | 0.0091 (5) | −0.0035 (6) |
C8 | 0.0230 (6) | 0.0303 (7) | 0.0340 (7) | −0.0005 (5) | 0.0082 (5) | −0.0015 (6) |
C9 | 0.0268 (6) | 0.0348 (8) | 0.0376 (7) | 0.0017 (6) | 0.0110 (5) | −0.0033 (6) |
C10 | 0.0328 (7) | 0.0265 (7) | 0.0350 (7) | −0.0008 (6) | 0.0141 (5) | −0.0035 (6) |
C11 | 0.0327 (7) | 0.0529 (11) | 0.0415 (8) | −0.0090 (7) | 0.0154 (6) | −0.0185 (8) |
C12 | 0.0394 (8) | 0.0549 (11) | 0.0498 (10) | −0.0084 (8) | 0.0215 (7) | −0.0197 (9) |
C13 | 0.0495 (10) | 0.113 (2) | 0.0363 (9) | −0.0085 (13) | 0.0101 (8) | −0.0244 (13) |
C14 | 0.0410 (8) | 0.0372 (9) | 0.0424 (8) | −0.0019 (7) | 0.0216 (7) | −0.0035 (7) |
C15 | 0.0275 (7) | 0.0532 (11) | 0.0486 (9) | −0.0020 (8) | 0.0119 (6) | 0.0036 (9) |
C16 | 0.0260 (7) | 0.0386 (9) | 0.0544 (9) | −0.0029 (6) | 0.0137 (6) | −0.0057 (8) |
C17 | 0.0269 (8) | 0.0598 (13) | 0.0730 (13) | −0.0051 (9) | 0.0004 (8) | −0.0095 (11) |
O1—C2 | 1.2274 (18) | C8—C9 | 1.528 (2) |
O2—C12 | 1.361 (2) | C8—H8 | 1.0000 |
O2—C6 | 1.4560 (16) | C9—C10 | 1.516 (2) |
O3—C12 | 1.195 (2) | C9—H9A | 0.9900 |
O4—C16 | 1.346 (2) | C9—H9B | 0.9900 |
O4—C8 | 1.4531 (16) | C10—C14 | 1.503 (2) |
O5—C16 | 1.194 (2) | C11—C12 | 1.514 (2) |
C1—C10 | 1.347 (2) | C11—C13 | 1.531 (3) |
C1—C2 | 1.4964 (19) | C11—H11 | 1.0000 |
C1—C5 | 1.5282 (19) | C13—H13A | 0.9800 |
C2—C3 | 1.464 (2) | C13—H13B | 0.9800 |
C3—C4 | 1.334 (2) | C13—H13C | 0.9800 |
C3—H3 | 0.9500 | C14—H14A | 0.9800 |
C4—C15 | 1.497 (2) | C14—H14B | 0.9800 |
C4—C5 | 1.5305 (19) | C14—H14C | 0.9800 |
C5—C6 | 1.529 (2) | C15—H15A | 0.9800 |
C5—H5 | 1.0000 | C15—H15B | 0.9800 |
C6—C7 | 1.5275 (19) | C15—H15C | 0.9800 |
C6—H6 | 1.0000 | C16—C17 | 1.495 (2) |
C7—C8 | 1.5167 (18) | C17—H17A | 0.9800 |
C7—C11 | 1.530 (2) | C17—H17B | 0.9800 |
C7—H7 | 1.0000 | C17—H17C | 0.9800 |
C12—O2—C6 | 108.82 (11) | C8—C9—H9B | 108.8 |
C16—O4—C8 | 117.07 (13) | H9A—C9—H9B | 107.7 |
C10—C1—C2 | 126.36 (13) | C1—C10—C14 | 124.24 (14) |
C10—C1—C5 | 126.45 (12) | C1—C10—C9 | 122.00 (13) |
C2—C1—C5 | 107.14 (12) | C14—C10—C9 | 113.76 (12) |
O1—C2—C3 | 125.08 (14) | C12—C11—C13 | 110.91 (16) |
O1—C2—C1 | 128.17 (14) | C12—C11—C7 | 100.92 (13) |
C3—C2—C1 | 106.73 (12) | C13—C11—C7 | 117.44 (19) |
C4—C3—C2 | 111.61 (13) | C12—C11—H11 | 109.0 |
C4—C3—H3 | 124.2 | C13—C11—H11 | 109.0 |
C2—C3—H3 | 124.2 | C7—C11—H11 | 109.0 |
C3—C4—C15 | 124.82 (14) | O3—C12—O2 | 121.48 (17) |
C3—C4—C5 | 111.45 (13) | O3—C12—C11 | 128.28 (18) |
C15—C4—C5 | 123.70 (14) | O2—C12—C11 | 110.24 (14) |
C1—C5—C4 | 103.03 (11) | C11—C13—H13A | 109.5 |
C1—C5—C6 | 109.48 (12) | C11—C13—H13B | 109.5 |
C4—C5—C6 | 114.26 (13) | H13A—C13—H13B | 109.5 |
C1—C5—H5 | 109.9 | C11—C13—H13C | 109.5 |
C4—C5—H5 | 109.9 | H13A—C13—H13C | 109.5 |
C6—C5—H5 | 109.9 | H13B—C13—H13C | 109.5 |
O2—C6—C7 | 103.37 (11) | C10—C14—H14A | 109.5 |
O2—C6—C5 | 111.25 (11) | C10—C14—H14B | 109.5 |
C7—C6—C5 | 115.19 (12) | H14A—C14—H14B | 109.5 |
O2—C6—H6 | 108.9 | C10—C14—H14C | 109.5 |
C7—C6—H6 | 108.9 | H14A—C14—H14C | 109.5 |
C5—C6—H6 | 108.9 | H14B—C14—H14C | 109.5 |
C8—C7—C6 | 112.84 (12) | C4—C15—H15A | 109.5 |
C8—C7—C11 | 117.26 (13) | C4—C15—H15B | 109.5 |
C6—C7—C11 | 100.82 (12) | H15A—C15—H15B | 109.5 |
C8—C7—H7 | 108.5 | C4—C15—H15C | 109.5 |
C6—C7—H7 | 108.5 | H15A—C15—H15C | 109.5 |
C11—C7—H7 | 108.5 | H15B—C15—H15C | 109.5 |
O4—C8—C7 | 105.89 (11) | O5—C16—O4 | 123.17 (16) |
O4—C8—C9 | 107.70 (12) | O5—C16—C17 | 126.12 (17) |
C7—C8—C9 | 111.55 (12) | O4—C16—C17 | 110.72 (17) |
O4—C8—H8 | 110.5 | C16—C17—H17A | 109.5 |
C7—C8—H8 | 110.5 | C16—C17—H17B | 109.5 |
C9—C8—H8 | 110.5 | H17A—C17—H17B | 109.5 |
C10—C9—C8 | 113.88 (13) | C16—C17—H17C | 109.5 |
C10—C9—H9A | 108.8 | H17A—C17—H17C | 109.5 |
C8—C9—H9A | 108.8 | H17B—C17—H17C | 109.5 |
C10—C9—H9B | 108.8 | ||
C10—C1—C2—O1 | 1.9 (3) | C16—O4—C8—C7 | −150.66 (14) |
C5—C1—C2—O1 | 179.44 (16) | C16—O4—C8—C9 | 89.89 (16) |
C10—C1—C2—C3 | −179.45 (16) | C6—C7—C8—O4 | 173.55 (12) |
C5—C1—C2—C3 | −1.92 (17) | C11—C7—C8—O4 | 57.06 (17) |
O1—C2—C3—C4 | −179.88 (17) | C6—C7—C8—C9 | −69.56 (17) |
C1—C2—C3—C4 | 1.43 (19) | C11—C7—C8—C9 | 173.95 (14) |
C2—C3—C4—C15 | −178.39 (17) | O4—C8—C9—C10 | −164.72 (12) |
C2—C3—C4—C5 | −0.3 (2) | C7—C8—C9—C10 | 79.49 (16) |
C10—C1—C5—C4 | 179.21 (16) | C2—C1—C10—C14 | −0.3 (3) |
C2—C1—C5—C4 | 1.69 (17) | C5—C1—C10—C14 | −177.38 (17) |
C10—C1—C5—C6 | 57.2 (2) | C2—C1—C10—C9 | 179.25 (16) |
C2—C1—C5—C6 | −120.27 (13) | C5—C1—C10—C9 | 2.2 (2) |
C3—C4—C5—C1 | −0.88 (18) | C8—C9—C10—C1 | −63.6 (2) |
C15—C4—C5—C1 | 177.21 (16) | C8—C9—C10—C14 | 116.04 (15) |
C3—C4—C5—C6 | 117.79 (16) | C8—C7—C11—C12 | 158.30 (15) |
C15—C4—C5—C6 | −64.1 (2) | C6—C7—C11—C12 | 35.41 (17) |
C12—O2—C6—C7 | 26.98 (18) | C8—C7—C11—C13 | −81.1 (2) |
C12—O2—C6—C5 | 151.16 (15) | C6—C7—C11—C13 | 156.06 (17) |
C1—C5—C6—O2 | 164.00 (12) | C6—O2—C12—O3 | 176.5 (2) |
C4—C5—C6—O2 | 49.05 (17) | C6—O2—C12—C11 | −3.5 (2) |
C1—C5—C6—C7 | −78.81 (15) | C13—C11—C12—O3 | 33.7 (4) |
C4—C5—C6—C7 | 166.25 (12) | C7—C11—C12—O3 | 158.9 (3) |
O2—C6—C7—C8 | −164.56 (12) | C13—C11—C12—O2 | −146.3 (2) |
C5—C6—C7—C8 | 73.88 (17) | C7—C11—C12—O2 | −21.1 (2) |
O2—C6—C7—C11 | −38.66 (15) | C8—O4—C16—O5 | −2.1 (3) |
C5—C6—C7—C11 | −160.22 (13) | C8—O4—C16—C17 | 178.04 (15) |
Experimental details
Crystal data | |
Chemical formula | C17H20O5 |
Mr | 304.33 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 173 |
a, b, c (Å) | 10.2083 (2), 7.5434 (2), 11.0118 (3) |
β (°) | 109.677 (1) |
V (Å3) | 798.45 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.25 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SORTAV: Blessing, 1995, 1997) |
Tmin, Tmax | 0.977, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4575, 2477, 2297 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.704 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.093, 1.07 |
No. of reflections | 2477 |
No. of parameters | 203 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.13 |
Computer programs: COLLECT (Hooft, 1998), HKL DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 1997), TEXSAN (Molecular Structure Corporation, 1994).
O1—C2 | 1.2274 (18) | O4—C16 | 1.346 (2) |
O2—C12 | 1.361 (2) | O4—C8 | 1.4531 (16) |
O2—C6 | 1.4560 (16) | O5—C16 | 1.194 (2) |
O3—C12 | 1.195 (2) | ||
C12—O2—C6 | 108.82 (11) | C16—O4—C8 | 117.07 (13) |
We have isolated a sesqiterpene lactone, matricarin, (I), from Achillea vermacularis (Compositae), collected from Tehran area. Martinez et al. (1988) have reported the NMR spectroscopic data for (I) and some related guanianolides without quoting the source of (I). In this paper, we report the structure of (I) which has been established by X-ray crystallographic method.
The structure of (I) is presented in Fig. 1. The molecular dimensions lie within expected values (Orpen et al., 1994) for the corresponding bond distances and angles with mean bond distances: Csp3—Csp3 1.527 (5), Csp3—Csp2 1.508 (11), Csp2—Csp2 1.480 (16), O—Csp3 1.455 (2), O—Csp2 1.354 (7), C═C 1.341 (6) and C═O 1.205 (15) Å. The seven-membered ring adopts a chair conformation wherein atoms C5/C6/C8/C9 are in a plane [maximum deviation 0.0096 (8) Å], with C7 0.744 (2) Å above and C1 and C10 1.012 (2) and 1.051 (2) Å, respectively, below this plane. The C1—C5 five-membered ring is essentially planar, with the maximum deviation of any atom being 0.0114 (10) Å. The other five-membered ring, O2/C7/C7/C11/C12, has a C7-envelope conformation with C7 0.608 (3) Å out of the plane of the remaining ring atoms. The structure is devoid of any classical hydrogen bonds.