Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100013950/na1483sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100013950/na1483CP44161sup2.hkl |
CCDC reference: 158267
CP44,161 was obtained from the pharmaceutical company Pfizer and was isolated from Dactylosporangium salmoneum Routien sp. nov. The sample of CP44,161 obtained from Pfizer was recrystallized from ethyl acetate.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1997); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN for Windows (Molecular Structure Corporation, 1997).
Fig. 1. An ORTEP (Johnson, 1976; Hall et al., 1999) depiction of CP44,161, with displacement ellipsoids shown at the 20% level. Unfilled bonds have been used to emphasize hydrogen bonds. |
C43H66O10·H2O | Dx = 1.156 Mg m−3 |
Mr = 760.97 | Mo Kα radiation, λ = 0.71069 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 12.373 (2) Å | θ = 8.5–11.9° |
b = 31.939 (2) Å | µ = 0.08 mm−1 |
c = 11.064 (2) Å | T = 294 K |
V = 4372.3 (11) Å3 | Plate, colourless |
Z = 4 | 0.34 × 0.32 × 0.17 mm |
F(000) = 1656 |
Rigaku AFC7R diffractometer | 2144 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.049 |
Graphite monochromator | θmax = 25.0°, θmin = 1.3° |
ω:θ scans | h = −1→14 |
Absorption correction: analytical de Meulenaer & Tompa (1965). | k = −1→37 |
Tmin = 0.97, Tmax = 0.99 | l = −1→13 |
5472 measured reflections | 3 standard reflections every 60 min |
4325 independent reflections | intensity decay: 0.0% |
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)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.059P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.94 | (Δ/σ)max < 0.001 |
4325 reflections | Δρmax = 0.14 e Å−3 |
508 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0043 (5) |
C43H66O10·H2O | V = 4372.3 (11) Å3 |
Mr = 760.97 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 12.373 (2) Å | µ = 0.08 mm−1 |
b = 31.939 (2) Å | T = 294 K |
c = 11.064 (2) Å | 0.34 × 0.32 × 0.17 mm |
Rigaku AFC7R diffractometer | 2144 reflections with I > 2σ(I) |
Absorption correction: analytical de Meulenaer & Tompa (1965). | Rint = 0.049 |
Tmin = 0.97, Tmax = 0.99 | 3 standard reflections every 60 min |
5472 measured reflections | intensity decay: 0.0% |
4325 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.126 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | Δρmax = 0.14 e Å−3 |
4325 reflections | Δρmin = −0.15 e Å−3 |
508 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 | ||
O1 | 0.2840 (3) | −0.06781 (10) | 0.1497 (3) | 0.0754 (9) | |
H1O | 0.2553 | −0.0724 | 0.0842 | 0.113* | |
O2 | 0.3503 (3) | −0.13124 (11) | 0.1172 (3) | 0.0871 (11) | |
O3 | 0.3947 (3) | −0.17610 (11) | 0.2989 (4) | 0.1016 (12) | |
H3O | 0.3805 | −0.1710 | 0.2280 | 0.152* | |
O4 | 0.3378 (2) | 0.07699 (10) | 0.4618 (2) | 0.0585 (7) | |
H4O | 0.3987 | 0.0730 | 0.4885 | 0.088* | |
O5 | 0.5290 (2) | 0.11810 (10) | 0.3052 (3) | 0.0741 (9) | |
O6 | 0.4956 (2) | 0.18001 (8) | 0.5411 (2) | 0.0572 (7) | |
O7 | 0.5879 (2) | 0.18158 (9) | 0.7166 (3) | 0.0629 (8) | |
O8 | 0.6581 (2) | 0.11512 (9) | 0.6746 (3) | 0.0639 (8) | |
O9 | 0.7749 (3) | 0.04601 (10) | 0.5754 (3) | 0.0722 (9) | |
O10 | 0.6262 (3) | −0.01011 (15) | 0.6772 (4) | 0.1078 (13) | |
H10O | 0.5997 | 0.0110 | 0.6474 | 0.162* | |
O11 | 0.5368 (3) | 0.06064 (13) | 0.5394 (4) | 0.0898 (12) | |
H11O | 0.584 (5) | 0.056 (2) | 0.483 (6) | 0.135* | |
H12O | 0.571 (5) | 0.0827 (19) | 0.583 (6) | 0.135* | |
C1 | 0.3379 (3) | −0.10128 (16) | 0.1846 (5) | 0.0650 (13) | |
C2 | 0.3771 (3) | −0.10044 (14) | 0.3102 (4) | 0.0600 (12) | |
C3 | 0.4023 (4) | −0.13976 (19) | 0.3616 (5) | 0.0783 (15) | |
C4 | 0.4334 (5) | −0.1436 (2) | 0.4812 (6) | 0.0942 (17) | |
C5 | 0.4482 (4) | −0.1078 (2) | 0.5452 (5) | 0.1002 (19) | |
H5 | 0.4721 | −0.1096 | 0.6247 | 0.120* | |
C6 | 0.4291 (4) | −0.06892 (19) | 0.4960 (5) | 0.0811 (14) | |
H6 | 0.4421 | −0.0452 | 0.5425 | 0.097* | |
C7 | 0.3907 (3) | −0.06421 (15) | 0.3787 (4) | 0.0634 (12) | |
C8 | 0.3739 (3) | −0.02060 (14) | 0.3325 (5) | 0.0716 (14) | |
H8A | 0.3858 | −0.0206 | 0.2459 | 0.086* | |
H8B | 0.4282 | −0.0026 | 0.3684 | 0.086* | |
C9 | 0.2622 (3) | −0.00169 (15) | 0.3578 (4) | 0.0675 (13) | |
H9A | 0.2072 | −0.0205 | 0.3271 | 0.081* | |
H9B | 0.2523 | 0.0007 | 0.4445 | 0.081* | |
C10 | 0.2466 (3) | 0.04121 (13) | 0.3007 (4) | 0.0598 (11) | |
H10 | 0.2485 | 0.0374 | 0.2128 | 0.072* | |
C11 | 0.3381 (3) | 0.07082 (13) | 0.3337 (4) | 0.0558 (11) | |
H11 | 0.4060 | 0.0568 | 0.3128 | 0.067* | |
C12 | 0.3398 (4) | 0.11396 (14) | 0.2741 (4) | 0.0598 (11) | |
H12 | 0.2774 | 0.1303 | 0.3012 | 0.072* | |
C13 | 0.4445 (4) | 0.13675 (14) | 0.3075 (4) | 0.0587 (11) | |
C14 | 0.4373 (4) | 0.18231 (14) | 0.3379 (4) | 0.0623 (12) | |
H14 | 0.3799 | 0.1942 | 0.2875 | 0.075* | |
C15 | 0.4005 (4) | 0.18652 (13) | 0.4697 (4) | 0.0588 (11) | |
H15 | 0.3497 | 0.1638 | 0.4870 | 0.071* | |
C16 | 0.3445 (4) | 0.22809 (13) | 0.4991 (5) | 0.0722 (14) | |
H16 | 0.3906 | 0.2511 | 0.4714 | 0.087* | |
C17 | 0.3304 (4) | 0.23179 (15) | 0.6342 (5) | 0.0790 (14) | |
H17A | 0.2749 | 0.2122 | 0.6598 | 0.095* | |
H17B | 0.3051 | 0.2598 | 0.6529 | 0.095* | |
C18 | 0.4322 (4) | 0.22334 (14) | 0.7062 (4) | 0.0717 (13) | |
H18 | 0.4847 | 0.2452 | 0.6856 | 0.086* | |
C19 | 0.4818 (3) | 0.18079 (14) | 0.6694 (4) | 0.0589 (12) | |
C20 | 0.4177 (4) | 0.14440 (14) | 0.7127 (4) | 0.0587 (11) | |
H20 | 0.3514 | 0.1392 | 0.6760 | 0.070* | |
C21 | 0.4486 (4) | 0.11930 (16) | 0.7988 (4) | 0.0694 (13) | |
H21 | 0.4025 | 0.0982 | 0.8255 | 0.083* | |
C22 | 0.5569 (4) | 0.12416 (16) | 0.8544 (4) | 0.0693 (13) | |
H22A | 0.5846 | 0.0969 | 0.8774 | 0.083* | |
H22B | 0.5511 | 0.1411 | 0.9268 | 0.083* | |
C23 | 0.6345 (4) | 0.14472 (16) | 0.7667 (4) | 0.0642 (13) | |
C24 | 0.7433 (4) | 0.15703 (17) | 0.8192 (4) | 0.0796 (15) | |
H24 | 0.7650 | 0.1353 | 0.8768 | 0.095* | |
C25 | 0.8166 (4) | 0.15393 (17) | 0.7098 (5) | 0.0822 (15) | |
H25A | 0.8896 | 0.1467 | 0.7341 | 0.099* | |
H25B | 0.8186 | 0.1804 | 0.6667 | 0.099* | |
C26 | 0.7687 (3) | 0.11968 (16) | 0.6302 (4) | 0.0672 (13) | |
C27 | 0.8246 (4) | 0.07725 (17) | 0.6497 (5) | 0.0750 (14) | |
H27 | 0.9002 | 0.0800 | 0.6246 | 0.090* | |
C28 | 0.8228 (4) | 0.05802 (17) | 0.7734 (4) | 0.0778 (15) | |
H28A | 0.7534 | 0.0624 | 0.8122 | 0.093* | |
H28B | 0.8792 | 0.0697 | 0.8241 | 0.093* | |
C29 | 0.8423 (4) | 0.01207 (18) | 0.7504 (5) | 0.0855 (16) | |
H29A | 0.7985 | −0.0050 | 0.8039 | 0.103* | |
H29B | 0.9178 | 0.0051 | 0.7628 | 0.103* | |
C30 | 0.8097 (4) | 0.00509 (17) | 0.6178 (4) | 0.0751 (14) | |
C31 | 0.7135 (5) | −0.02399 (16) | 0.6043 (5) | 0.0828 (15) | |
H31 | 0.6903 | −0.0236 | 0.5197 | 0.099* | |
C32 | 0.7369 (5) | −0.06876 (17) | 0.6397 (6) | 0.114 (2) | |
H32A | 0.7497 | −0.0702 | 0.7252 | 0.171* | |
H32B | 0.7998 | −0.0784 | 0.5973 | 0.171* | |
H32C | 0.6762 | −0.0861 | 0.6192 | 0.171* | |
C33 | 0.4489 (7) | −0.1866 (2) | 0.5387 (7) | 0.154 (3) | |
H33A | 0.4766 | −0.1833 | 0.6192 | 0.231* | |
H33B | 0.4991 | −0.2026 | 0.4913 | 0.231* | |
H33C | 0.3808 | −0.2009 | 0.5418 | 0.231* | |
C34 | 0.1345 (3) | 0.05906 (17) | 0.3331 (5) | 0.0783 (15) | |
H34A | 0.1268 | 0.0601 | 0.4194 | 0.117* | |
H34B | 0.0793 | 0.0414 | 0.2997 | 0.117* | |
H34C | 0.1275 | 0.0868 | 0.3005 | 0.117* | |
C35 | 0.3397 (4) | 0.11093 (18) | 0.1345 (4) | 0.0884 (16) | |
H35A | 0.3487 | 0.1384 | 0.1005 | 0.133* | |
H35B | 0.2723 | 0.0993 | 0.1076 | 0.133* | |
H35C | 0.3980 | 0.0932 | 0.1087 | 0.133* | |
C36 | 0.5412 (4) | 0.20660 (15) | 0.3090 (4) | 0.0786 (14) | |
H36A | 0.5354 | 0.2347 | 0.3417 | 0.094* | |
H36B | 0.6018 | 0.1929 | 0.3481 | 0.094* | |
C37 | 0.5625 (6) | 0.2092 (2) | 0.1753 (5) | 0.126 (3) | |
H37A | 0.5828 | 0.1821 | 0.1455 | 0.188* | |
H37B | 0.6199 | 0.2287 | 0.1604 | 0.188* | |
H37C | 0.4982 | 0.2185 | 0.1345 | 0.188* | |
C38 | 0.2341 (5) | 0.23157 (18) | 0.4353 (5) | 0.1061 (19) | |
H38A | 0.1904 | 0.2077 | 0.4557 | 0.159* | |
H38B | 0.2448 | 0.2324 | 0.3494 | 0.159* | |
H38C | 0.1982 | 0.2567 | 0.4610 | 0.159* | |
C39 | 0.4104 (5) | 0.22621 (18) | 0.8411 (5) | 0.1009 (19) | |
H39A | 0.3858 | 0.2539 | 0.8606 | 0.151* | |
H39B | 0.4756 | 0.2203 | 0.8848 | 0.151* | |
H39C | 0.3558 | 0.2062 | 0.8630 | 0.151* | |
C40 | 0.7479 (5) | 0.19898 (18) | 0.8837 (5) | 0.105 (2) | |
H40A | 0.7223 | 0.2206 | 0.8306 | 0.158* | |
H40B | 0.8211 | 0.2049 | 0.9069 | 0.158* | |
H40C | 0.7031 | 0.1980 | 0.9546 | 0.158* | |
C41 | 0.7626 (4) | 0.13192 (17) | 0.4979 (4) | 0.0779 (14) | |
H41A | 0.7220 | 0.1578 | 0.4911 | 0.094* | |
H41B | 0.7231 | 0.1104 | 0.4545 | 0.094* | |
C42 | 0.8725 (5) | 0.1379 (2) | 0.4375 (5) | 0.112 (2) | |
H42A | 0.9148 | 0.1574 | 0.4836 | 0.167* | |
H42B | 0.8623 | 0.1486 | 0.3572 | 0.167* | |
H42C | 0.9094 | 0.1115 | 0.4336 | 0.167* | |
C43 | 0.9039 (5) | −0.00879 (19) | 0.5394 (6) | 0.111 (2) | |
H43A | 0.8802 | −0.0115 | 0.4572 | 0.167* | |
H43B | 0.9304 | −0.0353 | 0.5677 | 0.167* | |
H43C | 0.9606 | 0.0117 | 0.5439 | 0.167* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.077 (2) | 0.077 (2) | 0.072 (2) | −0.004 (2) | −0.0067 (19) | −0.0098 (18) |
O2 | 0.080 (2) | 0.086 (2) | 0.095 (3) | 0.0075 (19) | −0.004 (2) | −0.034 (2) |
O3 | 0.091 (3) | 0.076 (2) | 0.138 (4) | 0.015 (2) | −0.009 (3) | −0.016 (3) |
O4 | 0.0479 (15) | 0.0786 (19) | 0.0491 (18) | −0.0058 (16) | −0.0069 (14) | −0.0041 (15) |
O5 | 0.0505 (18) | 0.079 (2) | 0.093 (2) | −0.0057 (17) | −0.0007 (19) | −0.010 (2) |
O6 | 0.0576 (18) | 0.0637 (17) | 0.0504 (18) | −0.0051 (15) | 0.0038 (15) | −0.0011 (15) |
O7 | 0.0591 (18) | 0.0708 (19) | 0.0588 (18) | −0.0177 (16) | −0.0035 (16) | −0.0020 (17) |
O8 | 0.0454 (16) | 0.083 (2) | 0.0636 (19) | −0.0072 (15) | −0.0091 (16) | −0.0104 (17) |
O9 | 0.0618 (19) | 0.095 (2) | 0.0602 (19) | 0.0144 (19) | −0.0111 (17) | −0.0059 (18) |
O10 | 0.066 (2) | 0.138 (4) | 0.120 (3) | 0.010 (2) | −0.003 (2) | 0.003 (3) |
O11 | 0.057 (2) | 0.102 (3) | 0.110 (3) | 0.009 (2) | −0.023 (2) | −0.029 (2) |
C1 | 0.040 (2) | 0.073 (3) | 0.082 (4) | −0.007 (2) | 0.012 (3) | −0.020 (3) |
C2 | 0.041 (2) | 0.070 (3) | 0.069 (3) | −0.004 (2) | −0.002 (2) | −0.012 (3) |
C3 | 0.058 (3) | 0.092 (4) | 0.085 (4) | 0.006 (3) | 0.005 (3) | −0.010 (3) |
C4 | 0.079 (4) | 0.113 (5) | 0.091 (5) | 0.034 (4) | 0.006 (4) | 0.000 (4) |
C5 | 0.074 (4) | 0.154 (6) | 0.072 (4) | 0.029 (4) | −0.003 (3) | 0.011 (4) |
C6 | 0.062 (3) | 0.110 (4) | 0.071 (3) | −0.006 (3) | 0.004 (3) | −0.019 (3) |
C7 | 0.040 (2) | 0.078 (3) | 0.072 (3) | −0.008 (2) | 0.008 (2) | −0.010 (3) |
C8 | 0.057 (3) | 0.071 (3) | 0.087 (4) | −0.021 (2) | 0.010 (3) | −0.018 (3) |
C9 | 0.049 (2) | 0.077 (3) | 0.077 (3) | −0.019 (2) | 0.010 (2) | −0.017 (3) |
C10 | 0.049 (2) | 0.079 (3) | 0.052 (2) | −0.011 (2) | 0.003 (2) | −0.009 (2) |
C11 | 0.042 (2) | 0.068 (3) | 0.057 (3) | −0.003 (2) | 0.001 (2) | −0.007 (2) |
C12 | 0.049 (2) | 0.072 (3) | 0.058 (3) | −0.004 (2) | −0.006 (2) | −0.001 (2) |
C13 | 0.055 (3) | 0.068 (3) | 0.053 (3) | −0.002 (2) | −0.004 (2) | 0.005 (2) |
C14 | 0.069 (3) | 0.065 (3) | 0.053 (3) | −0.011 (2) | −0.005 (2) | 0.010 (2) |
C15 | 0.058 (3) | 0.058 (3) | 0.060 (3) | −0.003 (2) | −0.007 (2) | 0.003 (2) |
C16 | 0.083 (3) | 0.055 (3) | 0.079 (4) | 0.007 (3) | 0.005 (3) | 0.007 (3) |
C17 | 0.080 (3) | 0.061 (3) | 0.096 (4) | 0.005 (3) | 0.010 (3) | −0.011 (3) |
C18 | 0.078 (3) | 0.061 (3) | 0.077 (3) | −0.005 (3) | 0.014 (3) | −0.021 (3) |
C19 | 0.053 (3) | 0.065 (3) | 0.059 (3) | −0.011 (2) | −0.002 (2) | −0.009 (2) |
C20 | 0.053 (2) | 0.062 (3) | 0.060 (3) | −0.012 (2) | 0.006 (2) | −0.006 (3) |
C21 | 0.064 (3) | 0.084 (3) | 0.061 (3) | −0.015 (3) | 0.004 (3) | 0.008 (3) |
C22 | 0.068 (3) | 0.084 (3) | 0.056 (3) | −0.007 (3) | −0.008 (3) | 0.005 (2) |
C23 | 0.062 (3) | 0.081 (3) | 0.050 (3) | −0.008 (3) | −0.007 (2) | −0.010 (3) |
C24 | 0.062 (3) | 0.115 (4) | 0.062 (3) | −0.022 (3) | −0.015 (3) | −0.006 (3) |
C25 | 0.053 (3) | 0.107 (4) | 0.086 (4) | −0.018 (3) | −0.008 (3) | −0.008 (3) |
C26 | 0.043 (2) | 0.094 (3) | 0.064 (3) | −0.006 (3) | −0.005 (2) | −0.006 (3) |
C27 | 0.049 (3) | 0.108 (4) | 0.068 (3) | −0.002 (3) | −0.008 (3) | −0.009 (3) |
C28 | 0.058 (3) | 0.115 (4) | 0.060 (3) | 0.003 (3) | −0.024 (2) | 0.006 (3) |
C29 | 0.067 (3) | 0.110 (4) | 0.080 (4) | 0.015 (3) | −0.021 (3) | 0.001 (3) |
C30 | 0.057 (3) | 0.098 (4) | 0.070 (3) | 0.021 (3) | −0.010 (3) | −0.001 (3) |
C31 | 0.075 (3) | 0.098 (4) | 0.076 (4) | 0.008 (3) | −0.013 (3) | 0.000 (3) |
C32 | 0.112 (5) | 0.099 (4) | 0.130 (5) | 0.003 (4) | −0.025 (5) | 0.011 (4) |
C33 | 0.167 (7) | 0.127 (5) | 0.168 (7) | 0.075 (6) | 0.008 (6) | 0.045 (5) |
C34 | 0.044 (2) | 0.107 (4) | 0.084 (3) | −0.007 (3) | −0.005 (3) | −0.001 (3) |
C35 | 0.079 (3) | 0.126 (4) | 0.060 (3) | −0.030 (4) | −0.011 (3) | 0.013 (3) |
C36 | 0.096 (3) | 0.081 (3) | 0.059 (3) | −0.032 (3) | 0.007 (3) | 0.006 (3) |
C37 | 0.156 (6) | 0.155 (6) | 0.066 (4) | −0.064 (5) | 0.017 (4) | 0.018 (4) |
C38 | 0.102 (4) | 0.106 (4) | 0.110 (5) | 0.036 (4) | −0.023 (4) | 0.005 (4) |
C39 | 0.103 (4) | 0.112 (4) | 0.088 (4) | −0.002 (4) | 0.008 (4) | −0.045 (3) |
C40 | 0.097 (4) | 0.134 (5) | 0.084 (4) | −0.038 (4) | −0.018 (4) | −0.035 (4) |
C41 | 0.072 (3) | 0.095 (3) | 0.067 (3) | −0.006 (3) | 0.000 (3) | 0.006 (3) |
C42 | 0.106 (5) | 0.138 (5) | 0.091 (4) | −0.005 (4) | 0.026 (4) | 0.020 (4) |
C43 | 0.089 (4) | 0.125 (5) | 0.119 (5) | 0.037 (4) | 0.013 (4) | 0.003 (4) |
O1—C1 | 1.318 (5) | C21—C22 | 1.483 (6) |
O1—H1O | 0.8200 | C21—H21 | 0.9300 |
O2—C1 | 1.223 (5) | C22—C23 | 1.515 (6) |
O3—C3 | 1.355 (6) | C22—H22A | 0.9700 |
O3—H3O | 0.8200 | C22—H22B | 0.9700 |
O4—C11 | 1.431 (5) | C23—C24 | 1.517 (6) |
O4—H4O | 0.8200 | C24—C25 | 1.516 (7) |
O5—C13 | 1.204 (5) | C24—C40 | 1.519 (7) |
O6—C19 | 1.430 (5) | C24—H24 | 0.9800 |
O6—C15 | 1.432 (5) | C25—C26 | 1.524 (6) |
O7—C19 | 1.413 (5) | C25—H25A | 0.9700 |
O7—C23 | 1.424 (6) | C25—H25B | 0.9700 |
O8—C23 | 1.420 (5) | C26—C41 | 1.516 (7) |
O8—C26 | 1.462 (5) | C26—C27 | 1.537 (7) |
O9—C27 | 1.432 (5) | C27—C28 | 1.501 (7) |
O9—C30 | 1.454 (6) | C27—H27 | 0.9800 |
O10—C31 | 1.419 (6) | C28—C29 | 1.509 (7) |
O10—H10O | 0.8200 | C28—H28A | 0.9700 |
O11—H11O | 0.87 (6) | C28—H28B | 0.9700 |
O11—H12O | 0.96 (6) | C29—C30 | 1.538 (7) |
C1—C2 | 1.473 (7) | C29—H29A | 0.9700 |
C2—C7 | 1.394 (6) | C29—H29B | 0.9700 |
C2—C3 | 1.413 (7) | C30—C31 | 1.517 (7) |
C3—C4 | 1.384 (8) | C30—C43 | 1.519 (7) |
C4—C5 | 1.357 (8) | C31—C32 | 1.511 (7) |
C4—C33 | 1.526 (8) | C31—H31 | 0.9800 |
C5—C6 | 1.376 (7) | C32—H32A | 0.9600 |
C5—H5 | 0.9300 | C32—H32B | 0.9600 |
C6—C7 | 1.390 (7) | C32—H32C | 0.9600 |
C6—H6 | 0.9300 | C33—H33A | 0.9600 |
C7—C8 | 1.498 (6) | C33—H33B | 0.9600 |
C8—C9 | 1.534 (6) | C33—H33C | 0.9600 |
C8—H8A | 0.9700 | C34—H34A | 0.9600 |
C8—H8B | 0.9700 | C34—H34B | 0.9600 |
C9—C10 | 1.521 (6) | C34—H34C | 0.9600 |
C9—H9A | 0.9700 | C35—H35A | 0.9600 |
C9—H9B | 0.9700 | C35—H35B | 0.9600 |
C10—C11 | 1.519 (6) | C35—H35C | 0.9600 |
C10—C34 | 1.543 (6) | C36—C37 | 1.506 (7) |
C10—H10 | 0.9800 | C36—H36A | 0.9700 |
C11—C12 | 1.528 (6) | C36—H36B | 0.9700 |
C11—H11 | 0.9800 | C37—H37A | 0.9600 |
C12—C13 | 1.532 (6) | C37—H37B | 0.9600 |
C12—C35 | 1.548 (6) | C37—H37C | 0.9600 |
C12—H12 | 0.9800 | C38—H38A | 0.9600 |
C13—C14 | 1.496 (6) | C38—H38B | 0.9600 |
C14—C15 | 1.533 (6) | C38—H38C | 0.9600 |
C14—C36 | 1.535 (6) | C39—H39A | 0.9600 |
C14—H14 | 0.9800 | C39—H39B | 0.9600 |
C15—C16 | 1.533 (6) | C39—H39C | 0.9600 |
C15—H15 | 0.9800 | C40—H40A | 0.9600 |
C16—C17 | 1.509 (7) | C40—H40B | 0.9600 |
C16—C38 | 1.542 (7) | C40—H40C | 0.9600 |
C16—H16 | 0.9800 | C41—C42 | 1.527 (7) |
C17—C18 | 1.515 (7) | C41—H41A | 0.9700 |
C17—H17A | 0.9700 | C41—H41B | 0.9700 |
C17—H17B | 0.9700 | C42—H42A | 0.9600 |
C18—C39 | 1.520 (7) | C42—H42B | 0.9600 |
C18—C19 | 1.545 (6) | C42—H42C | 0.9600 |
C18—H18 | 0.9800 | C43—H43A | 0.9600 |
C19—C20 | 1.486 (6) | C43—H43B | 0.9600 |
C20—C21 | 1.302 (6) | C43—H43C | 0.9600 |
C20—H20 | 0.9300 | ||
C1—O1—H1O | 109.5 | C23—C24—C40 | 116.2 (5) |
C3—O3—H3O | 109.5 | C25—C24—H24 | 108.0 |
C11—O4—H4O | 109.5 | C23—C24—H24 | 108.0 |
C19—O6—C15 | 116.6 (3) | C40—C24—H24 | 108.0 |
C19—O7—C23 | 120.4 (3) | C24—C25—C26 | 106.0 (4) |
C23—O8—C26 | 111.5 (3) | C24—C25—H25A | 110.5 |
C27—O9—C30 | 108.3 (4) | C26—C25—H25A | 110.5 |
C31—O10—H10O | 109.5 | C24—C25—H25B | 110.5 |
H11O—O11—H12O | 101 (5) | C26—C25—H25B | 110.5 |
O2—C1—O1 | 121.3 (5) | H25A—C25—H25B | 108.7 |
O2—C1—C2 | 123.3 (5) | O8—C26—C41 | 107.7 (4) |
O1—C1—C2 | 115.4 (4) | O8—C26—C25 | 104.0 (4) |
C7—C2—C3 | 119.5 (5) | C41—C26—C25 | 113.1 (4) |
C7—C2—C1 | 124.6 (5) | O8—C26—C27 | 106.6 (4) |
C3—C2—C1 | 115.8 (4) | C41—C26—C27 | 112.7 (4) |
O3—C3—C4 | 115.7 (6) | C25—C26—C27 | 112.1 (4) |
O3—C3—C2 | 122.7 (5) | O9—C27—C28 | 103.4 (4) |
C4—C3—C2 | 121.6 (5) | O9—C27—C26 | 109.9 (4) |
C5—C4—C3 | 117.5 (6) | C28—C27—C26 | 118.8 (4) |
C5—C4—C33 | 121.6 (6) | O9—C27—H27 | 108.1 |
C3—C4—C33 | 120.9 (7) | C28—C27—H27 | 108.1 |
C4—C5—C6 | 122.1 (6) | C26—C27—H27 | 108.1 |
C4—C5—H5 | 119.0 | C27—C28—C29 | 104.0 (4) |
C6—C5—H5 | 119.0 | C27—C28—H28A | 111.0 |
C5—C6—C7 | 121.7 (5) | C29—C28—H28A | 111.0 |
C5—C6—H6 | 119.2 | C27—C28—H28B | 111.0 |
C7—C6—H6 | 119.2 | C29—C28—H28B | 111.0 |
C6—C7—C2 | 117.3 (5) | H28A—C28—H28B | 109.0 |
C6—C7—C8 | 117.8 (5) | C28—C29—C30 | 105.1 (4) |
C2—C7—C8 | 124.7 (4) | C28—C29—H29A | 110.7 |
C7—C8—C9 | 115.4 (4) | C30—C29—H29A | 110.7 |
C7—C8—H8A | 108.4 | C28—C29—H29B | 110.7 |
C9—C8—H8A | 108.4 | C30—C29—H29B | 110.7 |
C7—C8—H8B | 108.4 | H29A—C29—H29B | 108.8 |
C9—C8—H8B | 108.4 | O9—C30—C31 | 106.6 (4) |
H8A—C8—H8B | 107.5 | O9—C30—C43 | 107.8 (4) |
C10—C9—C8 | 113.2 (4) | C31—C30—C43 | 111.6 (5) |
C10—C9—H9A | 108.9 | O9—C30—C29 | 104.8 (4) |
C8—C9—H9A | 108.9 | C31—C30—C29 | 112.8 (4) |
C10—C9—H9B | 108.9 | C43—C30—C29 | 112.7 (4) |
C8—C9—H9B | 108.9 | O10—C31—C32 | 107.1 (5) |
H9A—C9—H9B | 107.8 | O10—C31—C30 | 110.5 (4) |
C11—C10—C9 | 111.5 (4) | C32—C31—C30 | 113.8 (5) |
C11—C10—C34 | 112.6 (3) | O10—C31—H31 | 108.4 |
C9—C10—C34 | 110.5 (4) | C32—C31—H31 | 108.4 |
C11—C10—H10 | 107.3 | C30—C31—H31 | 108.4 |
C9—C10—H10 | 107.3 | C31—C32—H32A | 109.5 |
C34—C10—H10 | 107.3 | C31—C32—H32B | 109.5 |
O4—C11—C10 | 108.8 (3) | H32A—C32—H32B | 109.5 |
O4—C11—C12 | 107.7 (3) | C31—C32—H32C | 109.5 |
C10—C11—C12 | 117.9 (4) | H32A—C32—H32C | 109.5 |
O4—C11—H11 | 107.4 | H32B—C32—H32C | 109.5 |
C10—C11—H11 | 107.4 | C4—C33—H33A | 109.5 |
C12—C11—H11 | 107.4 | C4—C33—H33B | 109.5 |
C11—C12—C13 | 109.6 (4) | H33A—C33—H33B | 109.5 |
C11—C12—C35 | 112.0 (4) | C4—C33—H33C | 109.5 |
C13—C12—C35 | 105.7 (4) | H33A—C33—H33C | 109.5 |
C11—C12—H12 | 109.8 | H33B—C33—H33C | 109.5 |
C13—C12—H12 | 109.8 | C10—C34—H34A | 109.5 |
C35—C12—H12 | 109.8 | C10—C34—H34B | 109.5 |
O5—C13—C14 | 122.5 (4) | H34A—C34—H34B | 109.5 |
O5—C13—C12 | 119.7 (4) | C10—C34—H34C | 109.5 |
C14—C13—C12 | 117.8 (4) | H34A—C34—H34C | 109.5 |
C13—C14—C15 | 108.5 (4) | H34B—C34—H34C | 109.5 |
C13—C14—C36 | 113.2 (4) | C12—C35—H35A | 109.5 |
C15—C14—C36 | 113.7 (4) | C12—C35—H35B | 109.5 |
C13—C14—H14 | 107.0 | H35A—C35—H35B | 109.5 |
C15—C14—H14 | 107.0 | C12—C35—H35C | 109.5 |
C36—C14—H14 | 107.0 | H35A—C35—H35C | 109.5 |
O6—C15—C16 | 112.3 (4) | H35B—C35—H35C | 109.5 |
O6—C15—C14 | 105.6 (3) | C37—C36—C14 | 112.3 (4) |
C16—C15—C14 | 114.3 (4) | C37—C36—H36A | 109.1 |
O6—C15—H15 | 108.1 | C14—C36—H36A | 109.1 |
C16—C15—H15 | 108.1 | C37—C36—H36B | 109.1 |
C14—C15—H15 | 108.1 | C14—C36—H36B | 109.1 |
C17—C16—C15 | 109.3 (4) | H36A—C36—H36B | 107.9 |
C17—C16—C38 | 110.2 (4) | C36—C37—H37A | 109.5 |
C15—C16—C38 | 111.5 (4) | C36—C37—H37B | 109.5 |
C17—C16—H16 | 108.6 | H37A—C37—H37B | 109.5 |
C15—C16—H16 | 108.6 | C36—C37—H37C | 109.5 |
C38—C16—H16 | 108.6 | H37A—C37—H37C | 109.5 |
C16—C17—C18 | 114.2 (4) | H37B—C37—H37C | 109.5 |
C16—C17—H17A | 108.7 | C16—C38—H38A | 109.5 |
C18—C17—H17A | 108.7 | C16—C38—H38B | 109.5 |
C16—C17—H17B | 108.7 | H38A—C38—H38B | 109.5 |
C18—C17—H17B | 108.7 | C16—C38—H38C | 109.5 |
H17A—C17—H17B | 107.6 | H38A—C38—H38C | 109.5 |
C17—C18—C39 | 110.9 (4) | H38B—C38—H38C | 109.5 |
C17—C18—C19 | 110.4 (4) | C18—C39—H39A | 109.5 |
C39—C18—C19 | 112.5 (4) | C18—C39—H39B | 109.5 |
C17—C18—H18 | 107.6 | H39A—C39—H39B | 109.5 |
C39—C18—H18 | 107.6 | C18—C39—H39C | 109.5 |
C19—C18—H18 | 107.6 | H39A—C39—H39C | 109.5 |
O7—C19—O6 | 104.9 (3) | H39B—C39—H39C | 109.5 |
O7—C19—C20 | 113.0 (4) | C24—C40—H40A | 109.5 |
O6—C19—C20 | 111.7 (4) | C24—C40—H40B | 109.5 |
O7—C19—C18 | 104.8 (3) | H40A—C40—H40B | 109.5 |
O6—C19—C18 | 108.9 (4) | C24—C40—H40C | 109.5 |
C20—C19—C18 | 113.0 (4) | H40A—C40—H40C | 109.5 |
C21—C20—C19 | 124.1 (4) | H40B—C40—H40C | 109.5 |
C21—C20—H20 | 117.9 | C26—C41—C42 | 114.3 (4) |
C19—C20—H20 | 117.9 | C26—C41—H41A | 108.7 |
C20—C21—C22 | 120.3 (4) | C42—C41—H41A | 108.7 |
C20—C21—H21 | 119.9 | C26—C41—H41B | 108.7 |
C22—C21—H21 | 119.9 | C42—C41—H41B | 108.7 |
C21—C22—C23 | 110.7 (4) | H41A—C41—H41B | 107.6 |
C21—C22—H22A | 109.5 | C41—C42—H42A | 109.5 |
C23—C22—H22A | 109.5 | C41—C42—H42B | 109.5 |
C21—C22—H22B | 109.5 | H42A—C42—H42B | 109.5 |
C23—C22—H22B | 109.5 | C41—C42—H42C | 109.5 |
H22A—C22—H22B | 108.1 | H42A—C42—H42C | 109.5 |
O8—C23—O7 | 110.8 (4) | H42B—C42—H42C | 109.5 |
O8—C23—C22 | 107.5 (4) | C30—C43—H43A | 109.5 |
O7—C23—C22 | 110.5 (4) | C30—C43—H43B | 109.5 |
O8—C23—C24 | 105.4 (4) | H43A—C43—H43B | 109.5 |
O7—C23—C24 | 107.1 (4) | C30—C43—H43C | 109.5 |
C22—C23—C24 | 115.5 (4) | H43A—C43—H43C | 109.5 |
C25—C24—C23 | 102.0 (4) | H43B—C43—H43C | 109.5 |
C25—C24—C40 | 114.2 (4) | ||
O2—C1—C2—C7 | 162.1 (4) | C17—C18—C19—O7 | 164.9 (4) |
O1—C1—C2—C7 | −20.4 (6) | C39—C18—C19—O7 | −70.6 (5) |
O2—C1—C2—C3 | −17.6 (6) | C17—C18—C19—O6 | 53.1 (5) |
O1—C1—C2—C3 | 159.8 (4) | C39—C18—C19—O6 | 177.6 (4) |
C7—C2—C3—O3 | −177.6 (4) | C17—C18—C19—C20 | −71.7 (5) |
C1—C2—C3—O3 | 2.2 (6) | C39—C18—C19—C20 | 52.8 (6) |
C7—C2—C3—C4 | 4.4 (7) | O7—C19—C20—C21 | 10.0 (6) |
C1—C2—C3—C4 | −175.9 (5) | O6—C19—C20—C21 | 127.9 (5) |
O3—C3—C4—C5 | 176.1 (5) | C18—C19—C20—C21 | −108.8 (5) |
C2—C3—C4—C5 | −5.7 (8) | C19—C20—C21—C22 | −4.4 (7) |
O3—C3—C4—C33 | −4.6 (8) | C20—C21—C22—C23 | −25.9 (6) |
C2—C3—C4—C33 | 173.6 (5) | C26—O8—C23—O7 | 92.4 (4) |
C3—C4—C5—C6 | 2.7 (9) | C26—O8—C23—C22 | −146.8 (4) |
C33—C4—C5—C6 | −176.6 (6) | C26—O8—C23—C24 | −23.1 (5) |
C4—C5—C6—C7 | 1.7 (8) | C19—O7—C23—O8 | 70.8 (5) |
C5—C6—C7—C2 | −3.0 (7) | C19—O7—C23—C22 | −48.3 (5) |
C5—C6—C7—C8 | −179.1 (5) | C19—O7—C23—C24 | −174.8 (4) |
C3—C2—C7—C6 | 0.0 (6) | C21—C22—C23—O8 | −71.2 (5) |
C1—C2—C7—C6 | −179.7 (4) | C21—C22—C23—O7 | 49.8 (5) |
C3—C2—C7—C8 | 175.9 (4) | C21—C22—C23—C24 | 171.6 (4) |
C1—C2—C7—C8 | −3.9 (6) | O8—C23—C24—C25 | 32.6 (5) |
C6—C7—C8—C9 | −88.6 (5) | O7—C23—C24—C25 | −85.4 (5) |
C2—C7—C8—C9 | 95.6 (5) | C22—C23—C24—C25 | 151.1 (5) |
C7—C8—C9—C10 | −175.6 (4) | O8—C23—C24—C40 | 157.6 (4) |
C8—C9—C10—C11 | −52.0 (5) | O7—C23—C24—C40 | 39.6 (6) |
C8—C9—C10—C34 | −178.0 (4) | C22—C23—C24—C40 | −84.0 (6) |
C9—C10—C11—O4 | −62.6 (4) | C23—C24—C25—C26 | −30.6 (6) |
C34—C10—C11—O4 | 62.2 (5) | C40—C24—C25—C26 | −156.8 (4) |
C9—C10—C11—C12 | 174.5 (4) | C23—O8—C26—C41 | −116.7 (4) |
C34—C10—C11—C12 | −60.6 (5) | C23—O8—C26—C25 | 3.4 (5) |
O4—C11—C12—C13 | 63.2 (4) | C23—O8—C26—C27 | 122.1 (4) |
C10—C11—C12—C13 | −173.4 (4) | C24—C25—C26—O8 | 17.6 (5) |
O4—C11—C12—C35 | −179.8 (4) | C24—C25—C26—C41 | 134.1 (5) |
C10—C11—C12—C35 | −56.3 (5) | C24—C25—C26—C27 | −97.2 (5) |
C11—C12—C13—O5 | 43.7 (6) | C30—O9—C27—C28 | −37.7 (5) |
C35—C12—C13—O5 | −77.2 (6) | C30—O9—C27—C26 | −165.6 (4) |
C11—C12—C13—C14 | −138.3 (4) | O8—C26—C27—O9 | 65.3 (5) |
C35—C12—C13—C14 | 100.8 (5) | C41—C26—C27—O9 | −52.6 (5) |
O5—C13—C14—C15 | −100.9 (5) | C25—C26—C27—O9 | 178.5 (4) |
C12—C13—C14—C15 | 81.2 (5) | O8—C26—C27—C28 | −53.4 (5) |
O5—C13—C14—C36 | 26.4 (6) | C41—C26—C27—C28 | −171.4 (4) |
C12—C13—C14—C36 | −151.5 (4) | C25—C26—C27—C28 | 59.8 (6) |
C19—O6—C15—C16 | 57.1 (5) | O9—C27—C28—C29 | 36.2 (5) |
C19—O6—C15—C14 | −177.7 (3) | C26—C27—C28—C29 | 158.2 (4) |
C13—C14—C15—O6 | 80.5 (4) | C27—C28—C29—C30 | −21.8 (5) |
C36—C14—C15—O6 | −46.5 (5) | C27—O9—C30—C31 | 143.4 (4) |
C13—C14—C15—C16 | −155.5 (4) | C27—O9—C30—C43 | −96.7 (5) |
C36—C14—C15—C16 | 77.5 (5) | C27—O9—C30—C29 | 23.5 (5) |
O6—C15—C16—C17 | −49.6 (5) | C28—C29—C30—O9 | 0.0 (5) |
C14—C15—C16—C17 | −169.9 (4) | C28—C29—C30—C31 | −115.7 (5) |
O6—C15—C16—C38 | −171.7 (4) | C28—C29—C30—C43 | 116.9 (5) |
C14—C15—C16—C38 | 68.0 (5) | O9—C30—C31—O10 | −61.8 (5) |
C15—C16—C17—C18 | 49.9 (6) | C43—C30—C31—O10 | −179.3 (4) |
C38—C16—C17—C18 | 172.7 (4) | C29—C30—C31—O10 | 52.7 (6) |
C16—C17—C18—C39 | −178.0 (4) | O9—C30—C31—C32 | 177.6 (5) |
C16—C17—C18—C19 | −52.7 (5) | C43—C30—C31—C32 | 60.1 (6) |
C23—O7—C19—O6 | −103.5 (4) | C29—C30—C31—C32 | −67.9 (6) |
C23—O7—C19—C20 | 18.4 (5) | C13—C14—C36—C37 | 67.3 (6) |
C23—O7—C19—C18 | 141.9 (4) | C15—C14—C36—C37 | −168.2 (5) |
C15—O6—C19—O7 | −169.4 (3) | O8—C26—C41—C42 | −179.9 (5) |
C15—O6—C19—C20 | 67.9 (5) | C25—C26—C41—C42 | 65.8 (6) |
C15—O6—C19—C18 | −57.6 (4) | C27—C26—C41—C42 | −62.6 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O4i | 0.82 | 1.78 | 2.584 (4) | 165 |
O3—H3O···O2 | 0.82 | 1.80 | 2.529 (6) | 147 |
O4—H4O···O11 | 0.82 | 1.84 | 2.659 (4) | 175 |
O10—H10O···O11 | 0.82 | 2.13 | 2.942 (6) | 170 |
O11—H11O···O9 | 0.87 (6) | 2.60 (6) | 3.009 (4) | 110 (5) |
O11—H12O···O8 | 0.96 (6) | 1.80 (7) | 2.742 (5) | 167 (6) |
C8—H8A···O1 | 0.97 | 2.23 | 2.757 (5) | 113 |
C11—H11···O5 | 0.98 | 2.48 | 2.822 (5) | 100 |
Symmetry code: (i) −x+1/2, −y, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C43H66O10·H2O |
Mr | 760.97 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 294 |
a, b, c (Å) | 12.373 (2), 31.939 (2), 11.064 (2) |
V (Å3) | 4372.3 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.34 × 0.32 × 0.17 |
Data collection | |
Diffractometer | Rigaku AFC7R diffractometer |
Absorption correction | Analytical de Meulenaer & Tompa (1965). |
Tmin, Tmax | 0.97, 0.99 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5472, 4325, 2144 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.126, 0.94 |
No. of reflections | 4325 |
No. of parameters | 508 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.14, −0.15 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1997), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1995), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), TEXSAN for Windows (Molecular Structure Corporation, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O4i | 0.82 | 1.78 | 2.584 (4) | 165 |
O3—H3O···O2 | 0.82 | 1.80 | 2.529 (6) | 147 |
O4—H4O···O11 | 0.82 | 1.84 | 2.659 (4) | 175 |
O10—H10O···O11 | 0.82 | 2.13 | 2.942 (6) | 170 |
O11—H11O···O9 | 0.87 (6) | 2.60 (6) | 3.009 (4) | 110 (5) |
O11—H12O···O8 | 0.96 (6) | 1.80 (7) | 2.742 (5) | 167 (6) |
C8—H8A···O1 | 0.97 | 2.23 | 2.757 (5) | 113 |
C11—H11···O5 | 0.98 | 2.48 | 2.822 (5) | 100 |
Symmetry code: (i) −x+1/2, −y, z−1/2. |
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The polyether family of antibiotics has adopted an important role in that its members can act as ionophores transporting ions through biological membranes (Dobler, 1981). A fundamental property of many of the polyether antibiotics is their ability to adopt a cyclic conformation whereby several of the oxygen atoms present in the molecule's backbone are available to complex to a metal ion and transport the ion across a lipophilic membrane.
Salinomycin is a member of the polyether family of antibiotics that was isolated from Streptomyces albus. The structure of salinomycin was elucidated by X-ray analysis of its p-iodophenacyl ester (Kinashi et al., 1975). Salinomycin has a unique tricyclic bis-spiroacetal moiety that has been proposed to act as a hinge to aid metal binding. The cis stereochemistry of the bis-spiroacetal ring system is a key feature of the structure and is implicated in the mechanism of ionophoric action (Mronga et al., 1993).
Closely related to salinomycin is the polyether antibiotic CP44,161 which is produced by three strains of a Dactylosporangium species. CP44,161 exhibits anticoccidial activity and improves feed utilization efficiency in ruminants (Celmer et al., 1978). CP44,161 contains the same cis bis-spiroacetal ring system found in salinomycin. \sch
As part of our synthetic programme directed towards the synthesis of the bis-spiroacetal moiety of antibiotic CP44,161, we needed to establish the stereochemistry of the bis-spiroacetal ring system of our synthetic intermediates by comparison of the NMR data of our compounds with the natural product. In order to do this we needed to establish unequivocally the stereochemistry of bis-spiroacetal ring system of the naturally occurring antibiotic CP44,161 hence a crystallographic analysis of this natural product was carried out.
The crystal structure of CP44,161 (Fig. 1) establishes the cis stereochemistry of the bis-spiroacetal ring system, and demonstrates that the molecule can adopt a cyclic conformation. Presumably contributing to the stabilization of the cyclic conformation, a centrally located water molecule participates in hydrogen-bond interactions with O10 and O8 on one side, and with O4 on the other side of the molecule (Table 1). There is also a weak interaction between the water molecule and O9. The conformation may also be influenced by weak interactions between C8 and O1, and C11 and O5. An oligomeric hydrogen-bond network is formed with O1 hydrogen bonded to O4 on a neighbouring molecule (-x + 1/2, -y, z - 1/2).
The crystal structure of antibiotic CP44,161 suggests that the molecule is likely to be ionophoric, and it should be possible to replace the water molecule with a metal ion.