organic compounds
(20S)-22-Acetoxymethyl-6β-methoxy-3α,5-dihydro-3′H-cyclopropa[3α,5]-5α-pregnane
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
In the title steroid derivative, C25H40O3, the fused cyclopropane unit that corresponds to a part of the A ring has a β-configuration and the associated cyclopentane ring an envelope-shaped conformation.
Related literature
For the synthesis and et al. (2009). The of the acetoxymethyl title compound is that of the iodo-substituted compound.
of the iodo-substituted compound, see: KetulyExperimental
Crystal data
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).
Supporting information
10.1107/S1600536809020674/xu2534sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809020674/xu2534Isup2.hkl
(20S)-22-Iodomethyl-6-methoxy-3,5-dihydro-3'H-cyclopropa[3α,5]-5-pregnane (Ketuly et al., 2009) (250 mg) was dissolved in pyridine (2 ml) and acetic anhydride (2 ml). The solution was heated at 353 K for an hour. The solvent was evaporated to give a product (280 mg), which was purified by recrystallization from ethanol (140 mg); m.p. 395–396 K. M+ 338. C&H elemental analysis: calc. C 77.27, H 10.38% (found: C 77.06, H 10.44%).
Hydrogen atoms were placed at calculated positions (C–H 0.95–0.99 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times Ueq(C). 2271 Friedel pairs were merged.
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C25H40O3 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. |
C25H40O3 | F(000) = 428 |
Mr = 388.57 | Dx = 1.189 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 5999 reflections |
a = 9.8222 (1) Å | θ = 2.2–28.3° |
b = 7.6128 (1) Å | µ = 0.08 mm−1 |
c = 15.2309 (2) Å | T = 100 K |
β = 107.604 (1)° | Plate, colorless |
V = 1085.55 (2) Å3 | 0.30 × 0.10 × 0.02 mm |
Z = 2 |
Bruker SMART APEX diffractometer | 2550 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 27.5°, θmin = 2.2° |
ω scans | h = −12→12 |
10411 measured reflections | k = −9→9 |
2674 independent reflections | l = −19→19 |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0668P)2 + 0.103P] where P = (Fo2 + 2Fc2)/3 |
2674 reflections | (Δ/σ)max = 0.001 |
258 parameters | Δρmax = 0.30 e Å−3 |
1 restraint | Δρmin = −0.18 e Å−3 |
C25H40O3 | V = 1085.55 (2) Å3 |
Mr = 388.57 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.8222 (1) Å | µ = 0.08 mm−1 |
b = 7.6128 (1) Å | T = 100 K |
c = 15.2309 (2) Å | 0.30 × 0.10 × 0.02 mm |
β = 107.604 (1)° |
Bruker SMART APEX diffractometer | 2550 reflections with I > 2σ(I) |
10411 measured reflections | Rint = 0.023 |
2674 independent reflections |
R[F2 > 2σ(F2)] = 0.033 | 1 restraint |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.30 e Å−3 |
2674 reflections | Δρmin = −0.18 e Å−3 |
258 parameters |
x | y | z | Uiso*/Ueq | ||
O1 | 0.10395 (12) | 0.50018 (19) | 0.12290 (8) | 0.0237 (3) | |
O2 | 0.24166 (13) | 0.5963 (2) | 0.03933 (8) | 0.0286 (3) | |
O3 | 0.25451 (12) | 0.95997 (17) | 0.77203 (8) | 0.0214 (3) | |
C1 | 0.49210 (17) | 0.7214 (2) | 0.92678 (10) | 0.0213 (3) | |
H1C | 0.5064 | 0.8353 | 0.9597 | 0.026* | |
H1D | 0.4618 | 0.6239 | 0.9596 | 0.026* | |
C2 | 0.58913 (18) | 0.6782 (2) | 0.87028 (11) | 0.0206 (3) | |
H2 | 0.6654 | 0.7638 | 0.8683 | 0.025* | |
C3 | 0.6102 (2) | 0.4859 (3) | 0.85413 (12) | 0.0307 (4) | |
H3C | 0.6701 | 0.4288 | 0.9112 | 0.037* | |
H3D | 0.6561 | 0.4701 | 0.8050 | 0.037* | |
C4 | 0.4587 (2) | 0.4096 (2) | 0.82473 (12) | 0.0308 (4) | |
H4C | 0.4323 | 0.3696 | 0.8793 | 0.037* | |
H4D | 0.4524 | 0.3084 | 0.7829 | 0.037* | |
C5 | 0.35775 (17) | 0.5589 (2) | 0.77468 (10) | 0.0193 (3) | |
C6 | 0.2085 (2) | 0.5381 (3) | 0.78560 (12) | 0.0312 (4) | |
H6D | 0.2140 | 0.5544 | 0.8504 | 0.047* | |
H6E | 0.1719 | 0.4203 | 0.7655 | 0.047* | |
H6F | 0.1443 | 0.6263 | 0.7479 | 0.047* | |
C7 | 0.43341 (16) | 0.7250 (2) | 0.82255 (10) | 0.0158 (3) | |
C8 | 0.39518 (15) | 0.9004 (2) | 0.77576 (10) | 0.0153 (3) | |
H8 | 0.4669 | 0.9897 | 0.8092 | 0.018* | |
C9 | 0.23898 (18) | 0.9981 (3) | 0.86009 (12) | 0.0258 (4) | |
H9D | 0.1484 | 1.0596 | 0.8522 | 0.039* | |
H9E | 0.3183 | 1.0726 | 0.8949 | 0.039* | |
H9F | 0.2395 | 0.8882 | 0.8937 | 0.039* | |
C10 | 0.39576 (16) | 0.8908 (2) | 0.67622 (10) | 0.0158 (3) | |
H10C | 0.4951 | 0.8746 | 0.6749 | 0.019* | |
H10D | 0.3600 | 1.0032 | 0.6451 | 0.019* | |
C11 | 0.30351 (15) | 0.7405 (2) | 0.62360 (10) | 0.0133 (3) | |
H11 | 0.2021 | 0.7609 | 0.6217 | 0.016* | |
C12 | 0.35449 (16) | 0.5638 (2) | 0.67192 (10) | 0.0163 (3) | |
H12 | 0.4553 | 0.5475 | 0.6715 | 0.020* | |
C13 | 0.2681 (2) | 0.4112 (2) | 0.61596 (12) | 0.0254 (4) | |
H13C | 0.1674 | 0.4218 | 0.6155 | 0.030* | |
H13D | 0.3059 | 0.2990 | 0.6466 | 0.030* | |
C14 | 0.27319 (19) | 0.4064 (2) | 0.51608 (11) | 0.0221 (3) | |
H14C | 0.3725 | 0.3848 | 0.5159 | 0.027* | |
H14D | 0.2129 | 0.3087 | 0.4827 | 0.027* | |
C15 | 0.21989 (15) | 0.5799 (2) | 0.46676 (10) | 0.0149 (3) | |
C16 | 0.05902 (15) | 0.6053 (3) | 0.45320 (11) | 0.0224 (3) | |
H16D | 0.0426 | 0.6124 | 0.5135 | 0.034* | |
H16E | 0.0058 | 0.5056 | 0.4186 | 0.034* | |
H16F | 0.0264 | 0.7141 | 0.4189 | 0.034* | |
C17 | 0.31116 (15) | 0.7284 (2) | 0.52507 (10) | 0.0136 (3) | |
H17 | 0.4127 | 0.6996 | 0.5304 | 0.016* | |
C18 | 0.27348 (18) | 0.8908 (2) | 0.46325 (11) | 0.0190 (3) | |
H18E | 0.3526 | 0.9771 | 0.4791 | 0.023* | |
H18F | 0.1857 | 0.9479 | 0.4685 | 0.023* | |
C19 | 0.24985 (18) | 0.8151 (2) | 0.36523 (10) | 0.0212 (3) | |
H19C | 0.3268 | 0.8547 | 0.3403 | 0.025* | |
H19D | 0.1571 | 0.8552 | 0.3233 | 0.025* | |
C20 | 0.25155 (15) | 0.6111 (2) | 0.37410 (10) | 0.0155 (3) | |
H20 | 0.3516 | 0.5709 | 0.3823 | 0.019* | |
C21 | 0.15462 (16) | 0.5210 (2) | 0.28707 (10) | 0.0188 (3) | |
H21 | 0.0546 | 0.5633 | 0.2767 | 0.023* | |
C22 | 0.1550 (2) | 0.3196 (3) | 0.29402 (12) | 0.0285 (4) | |
H22A | 0.1066 | 0.2695 | 0.2333 | 0.043* | |
H22B | 0.1050 | 0.2838 | 0.3379 | 0.043* | |
H22C | 0.2538 | 0.2772 | 0.3153 | 0.043* | |
C23 | 0.20266 (16) | 0.5758 (2) | 0.20495 (10) | 0.0202 (3) | |
H23D | 0.2026 | 0.7054 | 0.1999 | 0.024* | |
H23E | 0.3007 | 0.5328 | 0.2126 | 0.024* | |
C24 | 0.13665 (17) | 0.5221 (2) | 0.04415 (11) | 0.0211 (3) | |
C25 | 0.0256 (2) | 0.4403 (4) | −0.03584 (12) | 0.0402 (5) | |
H25D | −0.0046 | 0.5256 | −0.0862 | 0.060* | |
H25E | −0.0570 | 0.4052 | −0.0165 | 0.060* | |
H25F | 0.0659 | 0.3367 | −0.0570 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0205 (5) | 0.0370 (7) | 0.0136 (5) | −0.0064 (5) | 0.0052 (4) | −0.0046 (5) |
O2 | 0.0325 (6) | 0.0348 (7) | 0.0209 (6) | −0.0102 (6) | 0.0118 (5) | −0.0031 (6) |
O3 | 0.0187 (5) | 0.0283 (6) | 0.0156 (5) | 0.0068 (5) | 0.0027 (4) | −0.0055 (5) |
C1 | 0.0284 (8) | 0.0204 (8) | 0.0125 (7) | 0.0008 (7) | 0.0024 (6) | 0.0001 (6) |
C2 | 0.0216 (8) | 0.0210 (8) | 0.0158 (7) | 0.0040 (6) | 0.0008 (6) | 0.0002 (6) |
C3 | 0.0431 (11) | 0.0242 (9) | 0.0185 (8) | 0.0145 (8) | 0.0001 (7) | 0.0013 (7) |
C4 | 0.0559 (12) | 0.0158 (8) | 0.0159 (8) | 0.0000 (9) | 0.0034 (7) | 0.0025 (7) |
C5 | 0.0296 (8) | 0.0149 (7) | 0.0123 (7) | −0.0046 (7) | 0.0046 (5) | 0.0008 (6) |
C6 | 0.0381 (10) | 0.0397 (11) | 0.0187 (8) | −0.0207 (9) | 0.0129 (7) | −0.0035 (8) |
C7 | 0.0185 (7) | 0.0160 (7) | 0.0123 (7) | 0.0002 (6) | 0.0037 (5) | −0.0004 (6) |
C8 | 0.0151 (6) | 0.0144 (7) | 0.0157 (7) | 0.0010 (6) | 0.0038 (5) | −0.0010 (6) |
C9 | 0.0210 (7) | 0.0358 (10) | 0.0205 (8) | 0.0039 (7) | 0.0063 (6) | −0.0081 (7) |
C10 | 0.0202 (7) | 0.0124 (7) | 0.0152 (7) | −0.0004 (6) | 0.0059 (5) | 0.0006 (6) |
C11 | 0.0148 (6) | 0.0127 (7) | 0.0126 (6) | 0.0004 (5) | 0.0045 (5) | 0.0000 (5) |
C12 | 0.0230 (7) | 0.0125 (7) | 0.0123 (7) | −0.0016 (6) | 0.0039 (5) | 0.0008 (6) |
C13 | 0.0446 (10) | 0.0127 (7) | 0.0162 (8) | −0.0077 (7) | 0.0053 (7) | 0.0005 (6) |
C14 | 0.0337 (9) | 0.0132 (7) | 0.0169 (8) | −0.0010 (7) | 0.0039 (6) | −0.0014 (6) |
C15 | 0.0177 (7) | 0.0150 (7) | 0.0128 (6) | −0.0004 (6) | 0.0061 (5) | −0.0010 (6) |
C16 | 0.0165 (7) | 0.0333 (9) | 0.0187 (7) | −0.0039 (7) | 0.0071 (5) | −0.0034 (7) |
C17 | 0.0151 (6) | 0.0130 (6) | 0.0129 (7) | 0.0003 (6) | 0.0046 (5) | 0.0003 (6) |
C18 | 0.0274 (8) | 0.0150 (7) | 0.0144 (7) | −0.0007 (6) | 0.0060 (6) | 0.0012 (6) |
C19 | 0.0307 (8) | 0.0195 (8) | 0.0131 (7) | −0.0020 (7) | 0.0064 (6) | 0.0019 (6) |
C20 | 0.0154 (6) | 0.0182 (7) | 0.0132 (7) | −0.0009 (6) | 0.0050 (5) | −0.0014 (6) |
C21 | 0.0183 (7) | 0.0250 (8) | 0.0133 (7) | −0.0040 (6) | 0.0049 (6) | −0.0035 (6) |
C22 | 0.0410 (10) | 0.0262 (9) | 0.0179 (8) | −0.0116 (8) | 0.0085 (7) | −0.0057 (7) |
C23 | 0.0201 (7) | 0.0265 (8) | 0.0134 (7) | −0.0044 (7) | 0.0039 (5) | −0.0033 (6) |
C24 | 0.0239 (7) | 0.0236 (8) | 0.0167 (7) | −0.0010 (6) | 0.0076 (6) | −0.0023 (6) |
C25 | 0.0399 (10) | 0.0626 (15) | 0.0185 (9) | −0.0212 (11) | 0.0092 (7) | −0.0084 (9) |
O1—C24 | 1.3425 (19) | C12—C13 | 1.536 (2) |
O1—C23 | 1.4491 (18) | C12—H12 | 1.0000 |
O2—C24 | 1.198 (2) | C13—C14 | 1.538 (2) |
O3—C9 | 1.4247 (19) | C13—H13C | 0.9900 |
O3—C8 | 1.4388 (18) | C13—H13D | 0.9900 |
C1—C2 | 1.501 (2) | C14—C15 | 1.532 (2) |
C1—C7 | 1.516 (2) | C14—H14C | 0.9900 |
C1—H1C | 0.9900 | C14—H14D | 0.9900 |
C1—H1D | 0.9900 | C15—C16 | 1.5425 (19) |
C2—C3 | 1.509 (2) | C15—C17 | 1.545 (2) |
C2—C7 | 1.524 (2) | C15—C20 | 1.5525 (19) |
C2—H2 | 1.0000 | C16—H16D | 0.9800 |
C3—C4 | 1.533 (3) | C16—H16E | 0.9800 |
C3—H3C | 0.9900 | C16—H16F | 0.9800 |
C3—H3D | 0.9900 | C17—C18 | 1.530 (2) |
C4—C5 | 1.549 (2) | C17—H17 | 1.0000 |
C4—H4C | 0.9900 | C18—C19 | 1.551 (2) |
C4—H4D | 0.9900 | C18—H18E | 0.9900 |
C5—C6 | 1.532 (2) | C18—H18F | 0.9900 |
C5—C7 | 1.535 (2) | C19—C20 | 1.559 (2) |
C5—C12 | 1.5562 (19) | C19—H19C | 0.9900 |
C6—H6D | 0.9800 | C19—H19D | 0.9900 |
C6—H6E | 0.9800 | C20—C21 | 1.540 (2) |
C6—H6F | 0.9800 | C20—H20 | 1.0000 |
C7—C8 | 1.507 (2) | C21—C23 | 1.523 (2) |
C8—C10 | 1.520 (2) | C21—C22 | 1.536 (3) |
C8—H8 | 1.0000 | C21—H21 | 1.0000 |
C9—H9D | 0.9800 | C22—H22A | 0.9800 |
C9—H9E | 0.9800 | C22—H22B | 0.9800 |
C9—H9F | 0.9800 | C22—H22C | 0.9800 |
C10—C11 | 1.527 (2) | C23—H23D | 0.9900 |
C10—H10C | 0.9900 | C23—H23E | 0.9900 |
C10—H10D | 0.9900 | C24—C25 | 1.503 (2) |
C11—C17 | 1.5279 (19) | C25—H25D | 0.9800 |
C11—C12 | 1.542 (2) | C25—H25E | 0.9800 |
C11—H11 | 1.0000 | C25—H25F | 0.9800 |
C24—O1—C23 | 116.28 (12) | C12—C13—H13C | 109.0 |
C9—O3—C8 | 113.69 (12) | C14—C13—H13C | 109.0 |
C2—C1—C7 | 60.67 (10) | C12—C13—H13D | 109.0 |
C2—C1—H1C | 117.7 | C14—C13—H13D | 109.0 |
C7—C1—H1C | 117.7 | H13C—C13—H13D | 107.8 |
C2—C1—H1D | 117.7 | C15—C14—C13 | 110.86 (13) |
C7—C1—H1D | 117.7 | C15—C14—H14C | 109.5 |
H1C—C1—H1D | 114.8 | C13—C14—H14C | 109.5 |
C1—C2—C3 | 116.65 (16) | C15—C14—H14D | 109.5 |
C1—C2—C7 | 60.16 (10) | C13—C14—H14D | 109.5 |
C3—C2—C7 | 108.47 (15) | H14C—C14—H14D | 108.1 |
C1—C2—H2 | 119.1 | C14—C15—C16 | 110.98 (14) |
C3—C2—H2 | 119.1 | C14—C15—C17 | 107.23 (12) |
C7—C2—H2 | 119.1 | C16—C15—C17 | 112.21 (13) |
C2—C3—C4 | 104.22 (16) | C14—C15—C20 | 116.41 (13) |
C2—C3—H3C | 110.9 | C16—C15—C20 | 109.75 (12) |
C4—C3—H3C | 110.9 | C17—C15—C20 | 99.78 (11) |
C2—C3—H3D | 110.9 | C15—C16—H16D | 109.5 |
C4—C3—H3D | 110.9 | C15—C16—H16E | 109.5 |
H3C—C3—H3D | 108.9 | H16D—C16—H16E | 109.5 |
C3—C4—C5 | 106.63 (14) | C15—C16—H16F | 109.5 |
C3—C4—H4C | 110.4 | H16D—C16—H16F | 109.5 |
C5—C4—H4C | 110.4 | H16E—C16—H16F | 109.5 |
C3—C4—H4D | 110.4 | C11—C17—C18 | 118.76 (13) |
C5—C4—H4D | 110.4 | C11—C17—C15 | 114.60 (12) |
H4C—C4—H4D | 108.6 | C18—C17—C15 | 104.30 (11) |
C6—C5—C7 | 112.04 (14) | C11—C17—H17 | 106.1 |
C6—C5—C4 | 111.19 (15) | C18—C17—H17 | 106.1 |
C7—C5—C4 | 103.00 (12) | C15—C17—H17 | 106.1 |
C6—C5—C12 | 112.47 (13) | C17—C18—C19 | 103.31 (13) |
C7—C5—C12 | 108.54 (12) | C17—C18—H18E | 111.1 |
C4—C5—C12 | 109.15 (14) | C19—C18—H18E | 111.1 |
C5—C6—H6D | 109.5 | C17—C18—H18F | 111.1 |
C5—C6—H6E | 109.5 | C19—C18—H18F | 111.1 |
H6D—C6—H6E | 109.5 | H18E—C18—H18F | 109.1 |
C5—C6—H6F | 109.5 | C18—C19—C20 | 106.99 (13) |
H6D—C6—H6F | 109.5 | C18—C19—H19C | 110.3 |
H6E—C6—H6F | 109.5 | C20—C19—H19C | 110.3 |
C8—C7—C1 | 118.20 (14) | C18—C19—H19D | 110.3 |
C8—C7—C2 | 120.24 (14) | C20—C19—H19D | 110.3 |
C1—C7—C2 | 59.17 (10) | H19C—C19—H19D | 108.6 |
C8—C7—C5 | 119.34 (12) | C21—C20—C15 | 118.22 (12) |
C1—C7—C5 | 117.30 (14) | C21—C20—C19 | 112.44 (13) |
C2—C7—C5 | 107.80 (13) | C15—C20—C19 | 103.36 (12) |
O3—C8—C7 | 113.39 (13) | C21—C20—H20 | 107.4 |
O3—C8—C10 | 105.61 (12) | C15—C20—H20 | 107.4 |
C7—C8—C10 | 110.70 (13) | C19—C20—H20 | 107.4 |
O3—C8—H8 | 109.0 | C23—C21—C22 | 109.58 (14) |
C7—C8—H8 | 109.0 | C23—C21—C20 | 108.70 (12) |
C10—C8—H8 | 109.0 | C22—C21—C20 | 113.40 (14) |
O3—C9—H9D | 109.5 | C23—C21—H21 | 108.3 |
O3—C9—H9E | 109.5 | C22—C21—H21 | 108.3 |
H9D—C9—H9E | 109.5 | C20—C21—H21 | 108.3 |
O3—C9—H9F | 109.5 | C21—C22—H22A | 109.5 |
H9D—C9—H9F | 109.5 | C21—C22—H22B | 109.5 |
H9E—C9—H9F | 109.5 | H22A—C22—H22B | 109.5 |
C8—C10—C11 | 112.28 (12) | C21—C22—H22C | 109.5 |
C8—C10—H10C | 109.1 | H22A—C22—H22C | 109.5 |
C11—C10—H10C | 109.1 | H22B—C22—H22C | 109.5 |
C8—C10—H10D | 109.1 | O1—C23—C21 | 107.87 (12) |
C11—C10—H10D | 109.1 | O1—C23—H23D | 110.1 |
H10C—C10—H10D | 107.9 | C21—C23—H23D | 110.1 |
C10—C11—C17 | 111.29 (12) | O1—C23—H23E | 110.1 |
C10—C11—C12 | 110.33 (11) | C21—C23—H23E | 110.1 |
C17—C11—C12 | 108.11 (12) | H23D—C23—H23E | 108.4 |
C10—C11—H11 | 109.0 | O2—C24—O1 | 123.80 (15) |
C17—C11—H11 | 109.0 | O2—C24—C25 | 124.99 (15) |
C12—C11—H11 | 109.0 | O1—C24—C25 | 111.21 (14) |
C13—C12—C11 | 110.47 (12) | C24—C25—H25D | 109.5 |
C13—C12—C5 | 112.33 (13) | C24—C25—H25E | 109.5 |
C11—C12—C5 | 113.93 (13) | H25D—C25—H25E | 109.5 |
C13—C12—H12 | 106.5 | C24—C25—H25F | 109.5 |
C11—C12—H12 | 106.5 | H25D—C25—H25F | 109.5 |
C5—C12—H12 | 106.5 | H25E—C25—H25F | 109.5 |
C12—C13—C14 | 112.90 (14) | ||
C7—C1—C2—C3 | −96.93 (17) | C4—C5—C12—C13 | 73.88 (17) |
C1—C2—C3—C4 | 47.2 (2) | C6—C5—C12—C11 | 76.57 (17) |
C7—C2—C3—C4 | −18.01 (19) | C7—C5—C12—C11 | −47.97 (17) |
C2—C3—C4—C5 | 30.41 (18) | C4—C5—C12—C11 | −159.54 (13) |
C3—C4—C5—C6 | −150.84 (15) | C11—C12—C13—C14 | 55.86 (19) |
C3—C4—C5—C7 | −30.67 (17) | C5—C12—C13—C14 | −175.72 (14) |
C3—C4—C5—C12 | 84.52 (16) | C12—C13—C14—C15 | −56.96 (19) |
C2—C1—C7—C8 | −110.21 (16) | C13—C14—C15—C16 | −67.31 (17) |
C2—C1—C7—C5 | 95.32 (16) | C13—C14—C15—C17 | 55.57 (16) |
C1—C2—C7—C8 | 106.81 (16) | C13—C14—C15—C20 | 166.22 (13) |
C3—C2—C7—C8 | −142.48 (15) | C10—C11—C17—C18 | −55.54 (16) |
C3—C2—C7—C1 | 110.71 (16) | C12—C11—C17—C18 | −176.85 (13) |
C1—C2—C7—C5 | −111.68 (14) | C10—C11—C17—C15 | −179.67 (12) |
C3—C2—C7—C5 | −0.96 (18) | C12—C11—C17—C15 | 59.02 (15) |
C6—C5—C7—C8 | −79.26 (17) | C14—C15—C17—C11 | −59.41 (16) |
C4—C5—C7—C8 | 161.16 (15) | C16—C15—C17—C11 | 62.70 (17) |
C12—C5—C7—C8 | 45.53 (18) | C20—C15—C17—C11 | 178.85 (12) |
C6—C5—C7—C1 | 74.92 (18) | C14—C15—C17—C18 | 169.08 (12) |
C4—C5—C7—C1 | −44.66 (17) | C16—C15—C17—C18 | −68.81 (15) |
C12—C5—C7—C1 | −160.29 (13) | C20—C15—C17—C18 | 47.34 (14) |
C6—C5—C7—C2 | 138.82 (14) | C11—C17—C18—C19 | −163.91 (12) |
C4—C5—C7—C2 | 19.24 (16) | C15—C17—C18—C19 | −34.87 (15) |
C12—C5—C7—C2 | −96.40 (14) | C17—C18—C19—C20 | 8.70 (17) |
C9—O3—C8—C7 | 65.98 (17) | C14—C15—C20—C21 | 79.65 (17) |
C9—O3—C8—C10 | −172.64 (14) | C16—C15—C20—C21 | −47.44 (19) |
C1—C7—C8—O3 | −84.03 (16) | C17—C15—C20—C21 | −165.44 (13) |
C2—C7—C8—O3 | −152.90 (13) | C14—C15—C20—C19 | −155.41 (14) |
C5—C7—C8—O3 | 69.91 (17) | C16—C15—C20—C19 | 77.50 (16) |
C1—C7—C8—C10 | 157.49 (13) | C17—C15—C20—C19 | −40.50 (14) |
C2—C7—C8—C10 | 88.62 (16) | C18—C19—C20—C21 | 148.82 (13) |
C5—C7—C8—C10 | −48.57 (18) | C18—C19—C20—C15 | 20.22 (16) |
O3—C8—C10—C11 | −70.54 (16) | C15—C20—C21—C23 | 177.98 (14) |
C7—C8—C10—C11 | 52.56 (16) | C19—C20—C21—C23 | 57.63 (17) |
C8—C10—C11—C17 | −177.44 (12) | C15—C20—C21—C22 | −59.89 (19) |
C8—C10—C11—C12 | −57.44 (16) | C19—C20—C21—C22 | 179.76 (15) |
C10—C11—C12—C13 | −176.47 (13) | C24—O1—C23—C21 | −174.41 (14) |
C17—C11—C12—C13 | −54.57 (16) | C22—C21—C23—O1 | 59.70 (18) |
C10—C11—C12—C5 | 55.99 (16) | C20—C21—C23—O1 | −175.88 (13) |
C17—C11—C12—C5 | 177.89 (12) | C23—O1—C24—O2 | 1.3 (3) |
C6—C5—C12—C13 | −50.0 (2) | C23—O1—C24—C25 | −179.22 (17) |
C7—C5—C12—C13 | −174.54 (13) |
Experimental details
Crystal data | |
Chemical formula | C25H40O3 |
Mr | 388.57 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 100 |
a, b, c (Å) | 9.8222 (1), 7.6128 (1), 15.2309 (2) |
β (°) | 107.604 (1) |
V (Å3) | 1085.55 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.10 × 0.02 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10411, 2674, 2550 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.092, 1.05 |
No. of reflections | 2674 |
No. of parameters | 258 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.18 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).
Acknowledgements
We thank the University of Malaya for supporting this study.
References
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–211. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ketuly, K. A. A., Hadi, A. H. & Ng, S. W. (2009). Acta Cryst. E65, o1125. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar
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