Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801020475/om6072sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801020475/om6072Isup2.hkl |
CCDC reference: 180529
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.043
- wR factor = 0.112
- Data-to-parameter ratio = 10.9
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
SHFSU_01 Alert C The absolute value of parameter shift to su ratio > 0.05 Absolute value of the parameter shift to su ratio given 0.056 Additional refinement cycles may be required. THETM_01 Alert C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5883 PLAT_302 Alert C Anion/Solvent Disorder ....................... 12.00 Perc. PLAT_601 Alert C Structure Contains Solvent Accessible VOIDS of 52.00 A 3 PLAT_731 Alert C Bond Calc 0.88(4), Rep 0.874(18) .... 2.22 s.u-Ratio O2S -H2SB 1.555 1.555 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 65.10 From the CIF: _reflns_number_total 10567 Count of symmetry unique reflns 7221 Completeness (_total/calc) 146.34% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3346 Fraction of Friedel pairs measured 0.463 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
5 Alert Level C = Please check
The peptide, Boc-Tyr-D-Ala-Gly-NMe-Phe-Met-OMe, was supplied by Research Triangle Institute and was prepared using standard methods of peptide synthesis. Crystals were grown by vapor diffusion of petroleum ether into acetone.
The displacement parameters of the terminal methyl group on the disordered methionine side chain were constrained using the ISOR instruction in SHELXTL (Sheldrick, 1997b). Difference peaks for the H atoms on two of the water molecules were located. The positions of these H atoms were refined with the O—H and H···H distances constrained to reasonable values. [Please explain the additional parts of the molecular formula, i.e.. H2O.0.125O]
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXS97.
C35H49N5O9S·H2O·0.125O | F(000) = 3144 |
Mr = 735.87 | Dx = 1.220 Mg m−3 |
Monoclinic, C2 | Cu Kα radiation, λ = 1.54178 Å |
a = 38.354 (1) Å | Cell parameters from 928 reflections |
b = 11.000 (1) Å | θ = 5.5–124.6° |
c = 22.689 (1) Å | µ = 1.21 mm−1 |
β = 123.15 (1)° | T = 153 K |
V = 8014.4 (8) Å3 | Prism, colorless |
Z = 8 | 0.52 × 0.50 × 0.46 mm |
Bruker SMART 6000 CCD diffractometer | 10567 independent reflections |
Radiation source: rotating anode | 8802 reflections with I > 2σ(I) |
Gobel optics monochromator | Rint = 0.033 |
ω scans | θmax = 65.1°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −42→44 |
Tmin = 0.559, Tmax = 0.573 | k = −12→12 |
17149 measured reflections | l = −26→25 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0576P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.112 | (Δ/σ)max = 0.056 |
S = 1.01 | Δρmax = 0.22 e Å−3 |
10567 reflections | Δρmin = −0.23 e Å−3 |
966 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
11 restraints | Extinction coefficient: 0.000290 (16) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.00 (2) |
C35H49N5O9S·H2O·0.125O | V = 8014.4 (8) Å3 |
Mr = 735.87 | Z = 8 |
Monoclinic, C2 | Cu Kα radiation |
a = 38.354 (1) Å | µ = 1.21 mm−1 |
b = 11.000 (1) Å | T = 153 K |
c = 22.689 (1) Å | 0.52 × 0.50 × 0.46 mm |
β = 123.15 (1)° |
Bruker SMART 6000 CCD diffractometer | 10567 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 8802 reflections with I > 2σ(I) |
Tmin = 0.559, Tmax = 0.573 | Rint = 0.033 |
17149 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.112 | Δρmax = 0.22 e Å−3 |
S = 1.01 | Δρmin = −0.23 e Å−3 |
10567 reflections | Absolute structure: Flack (1983) |
966 parameters | Absolute structure parameter: 0.00 (2) |
11 restraints |
Experimental. Final cell refinement and decay correction applied after integration as part of merge process in SAINT v6.02 A. |
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 | Occ. (<1) | |
C1 | 0.20958 (8) | −0.1808 (3) | 0.67153 (17) | 0.0599 (8) | |
C2 | 0.17653 (10) | −0.2765 (3) | 0.63626 (18) | 0.0697 (9) | |
H2A | 0.1551 | −0.2607 | 0.6449 | 0.105* | |
H2B | 0.1886 | −0.3549 | 0.6548 | 0.105* | |
H2C | 0.1648 | −0.2751 | 0.5865 | 0.105* | |
C3 | 0.24368 (10) | −0.2013 (4) | 0.6584 (2) | 0.0997 (12) | |
H3A | 0.2317 | −0.2074 | 0.6087 | 0.150* | |
H3B | 0.2582 | −0.2753 | 0.6810 | 0.150* | |
H3C | 0.2628 | −0.1344 | 0.6772 | 0.150* | |
C4 | 0.22749 (10) | −0.1709 (3) | 0.74995 (17) | 0.0797 (12) | |
H4A | 0.2053 | −0.1594 | 0.7571 | 0.119* | |
H4B | 0.2462 | −0.1029 | 0.7691 | 0.119* | |
H4C | 0.2423 | −0.2441 | 0.7731 | 0.119* | |
C5 | 0.16102 (7) | −0.0091 (2) | 0.63663 (12) | 0.0429 (6) | |
O0 | 0.14031 (5) | −0.05678 (18) | 0.65617 (10) | 0.0570 (5) | |
O | 0.19344 (5) | −0.06060 (17) | 0.63914 (10) | 0.0520 (5) | |
N1 | 0.15405 (5) | 0.10180 (19) | 0.60842 (10) | 0.0427 (5) | |
H1A | 0.1692 | 0.1257 | 0.5933 | 0.051* | |
C1A | 0.12238 (6) | 0.1850 (2) | 0.60159 (12) | 0.0397 (6) | |
H1AA | 0.1055 | 0.1437 | 0.6159 | 0.048* | |
C1B | 0.14382 (7) | 0.2956 (3) | 0.64876 (14) | 0.0517 (7) | |
H1BA | 0.1609 | 0.2677 | 0.6971 | 0.062* | |
H1BB | 0.1624 | 0.3303 | 0.6367 | 0.062* | |
C1G | 0.11589 (7) | 0.3949 (3) | 0.64524 (13) | 0.0459 (6) | |
C1D1 | 0.10570 (7) | 0.4047 (3) | 0.69560 (14) | 0.0502 (7) | |
H1DA | 0.1140 | 0.3435 | 0.7290 | 0.060* | |
C1E1 | 0.08386 (8) | 0.5020 (3) | 0.69700 (14) | 0.0538 (7) | |
H1EA | 0.0776 | 0.5061 | 0.7311 | 0.065* | |
C1Z | 0.07112 (7) | 0.5943 (3) | 0.64781 (14) | 0.0518 (7) | |
O1Z | 0.05121 (6) | 0.6921 (2) | 0.65272 (11) | 0.0656 (5) | |
H1ZA | 0.0523 | 0.7490 | 0.6304 | 0.098* | |
C1E2 | 0.07910 (8) | 0.5834 (3) | 0.59531 (15) | 0.0553 (7) | |
H1EB | 0.0692 | 0.6420 | 0.5601 | 0.066* | |
C1D2 | 0.10167 (8) | 0.4864 (3) | 0.59507 (14) | 0.0521 (7) | |
H1DB | 0.1075 | 0.4821 | 0.5604 | 0.062* | |
C1' | 0.09493 (6) | 0.2200 (2) | 0.52390 (12) | 0.0366 (5) | |
O1 | 0.11108 (5) | 0.26260 (18) | 0.49390 (9) | 0.0466 (4) | |
N2 | 0.05439 (5) | 0.19929 (19) | 0.49064 (9) | 0.0369 (5) | |
H2D | 0.0443 | 0.1694 | 0.5132 | 0.044* | |
C2A | 0.02686 (7) | 0.2271 (2) | 0.41571 (12) | 0.0408 (6) | |
H2AA | 0.0419 | 0.2124 | 0.3927 | 0.049* | |
C2B | 0.01257 (9) | 0.3586 (3) | 0.40377 (17) | 0.0650 (9) | |
H2BA | 0.0364 | 0.4112 | 0.4238 | 0.097* | |
H2BB | −0.0024 | 0.3737 | 0.4258 | 0.097* | |
H2BC | −0.0053 | 0.3739 | 0.3542 | 0.097* | |
C2' | −0.01032 (6) | 0.1425 (2) | 0.38413 (11) | 0.0375 (5) | |
O2 | −0.02728 (5) | 0.11913 (17) | 0.41595 (8) | 0.0462 (4) | |
N3 | −0.02403 (6) | 0.0995 (2) | 0.32083 (10) | 0.0485 (6) | |
H3D | −0.0107 | 0.1153 | 0.3012 | 0.058* | |
C3A | −0.06148 (8) | 0.0259 (3) | 0.28388 (13) | 0.0576 (8) | |
H3AA | −0.0814 | 0.0563 | 0.2940 | 0.069* | |
H3AB | −0.0547 | −0.0572 | 0.3008 | 0.069* | |
C3' | −0.08088 (7) | 0.0273 (2) | 0.20562 (12) | 0.0418 (6) | |
O3 | −0.06220 (5) | 0.07265 (18) | 0.18080 (8) | 0.0488 (5) | |
N4 | −0.11845 (5) | −0.0263 (2) | 0.16651 (10) | 0.0421 (5) | |
C4N | −0.14027 (8) | −0.0751 (3) | 0.19829 (14) | 0.0566 (7) | |
H4NA | −0.1227 | −0.1328 | 0.2343 | 0.085* | |
H4NB | −0.1655 | −0.1145 | 0.1627 | 0.085* | |
H4NC | −0.1469 | −0.0098 | 0.2187 | 0.085* | |
C4A | −0.13759 (7) | −0.0420 (3) | 0.09079 (12) | 0.0426 (6) | |
H4AA | −0.1199 | −0.0008 | 0.0782 | 0.051* | |
C4B | −0.14080 (8) | −0.1754 (3) | 0.06996 (14) | 0.0498 (7) | |
H4BA | −0.1569 | −0.2190 | 0.0845 | 0.060* | |
H4BB | −0.1555 | −0.1813 | 0.0191 | 0.060* | |
C4G | −0.09864 (8) | −0.2339 (3) | 0.10298 (15) | 0.0532 (7) | |
C4D1 | −0.07727 (8) | −0.2767 (3) | 0.17159 (15) | 0.0559 (7) | |
H4DA | −0.0899 | −0.2732 | 0.1968 | 0.067* | |
C4E1 | −0.03787 (9) | −0.3242 (3) | 0.20317 (19) | 0.0721 (10) | |
H4EA | −0.0239 | −0.3504 | 0.2497 | 0.087* | |
C4Z | −0.01912 (10) | −0.3331 (4) | 0.1665 (2) | 0.0838 (12) | |
H4ZA | 0.0073 | −0.3668 | 0.1876 | 0.101* | |
C4E2 | −0.03971 (10) | −0.2917 (4) | 0.0982 (2) | 0.0873 (11) | |
H4EB | −0.0270 | −0.2976 | 0.0732 | 0.105* | |
C4D2 | −0.07948 (10) | −0.2410 (4) | 0.06578 (18) | 0.0727 (9) | |
H4DB | −0.0930 | −0.2123 | 0.0198 | 0.087* | |
C4' | −0.18029 (7) | 0.0191 (3) | 0.05022 (14) | 0.0490 (7) | |
O4 | −0.21055 (6) | −0.0231 (2) | 0.04811 (14) | 0.0864 (8) | |
N5 | −0.18228 (6) | 0.1214 (2) | 0.01828 (11) | 0.0468 (5) | |
H5A | −0.1601 | 0.1476 | 0.0216 | 0.056* | |
C5A | −0.22011 (7) | 0.1912 (3) | −0.02197 (14) | 0.0478 (6) | |
H5AA | −0.2349 | 0.1880 | 0.0022 | 0.057* | |
C5B | −0.20982 (8) | 0.3234 (3) | −0.02593 (15) | 0.0528 (7) | |
H5BA | −0.2347 | 0.3672 | −0.0606 | 0.063* | |
H5BB | −0.1896 | 0.3286 | −0.0389 | 0.063* | |
C5G | −0.19136 (19) | 0.3783 (7) | 0.0496 (3) | 0.0625 (19) | 0.607 (2) |
H5GA | −0.1768 | 0.3149 | 0.0845 | 0.075* | 0.607 (2) |
H5GB | −0.2140 | 0.4072 | 0.0533 | 0.075* | 0.607 (2) |
S5 | −0.15525 (4) | 0.50422 (12) | 0.06840 (7) | 0.0620 (4) | 0.607 (2) |
C5D | −0.1079 (2) | 0.4096 (9) | 0.0885 (6) | 0.119 (4) | 0.607 (2) |
H5DA | −0.0849 | 0.4627 | 0.1012 | 0.178* | 0.607 (2) |
H5DB | −0.1147 | 0.3637 | 0.0475 | 0.178* | 0.607 (2) |
H5DC | −0.1003 | 0.3550 | 0.1267 | 0.178* | 0.607 (2) |
C5G' | −0.1902 (3) | 0.4046 (13) | 0.0377 (7) | 0.078 (4) | 0.393 (2) |
H5GC | −0.2105 | 0.4150 | 0.0502 | 0.094* | 0.393 (2) |
H5GD | −0.1865 | 0.4837 | 0.0230 | 0.094* | 0.393 (2) |
S5' | −0.14488 (9) | 0.3684 (3) | 0.11194 (14) | 0.1068 (11) | 0.393 (2) |
C5D' | −0.1132 (4) | 0.4301 (13) | 0.0774 (6) | 0.071 (3) | 0.393 (2) |
H5DD | −0.0841 | 0.4239 | 0.1134 | 0.106* | 0.393 (2) |
H5DE | −0.1203 | 0.5138 | 0.0643 | 0.106* | 0.393 (2) |
H5DF | −0.1191 | 0.3839 | 0.0370 | 0.106* | 0.393 (2) |
C5' | −0.24805 (7) | 0.1370 (3) | −0.09479 (13) | 0.0447 (6) | |
O5 | −0.23548 (6) | 0.0820 (2) | −0.12542 (10) | 0.0634 (6) | |
O5' | −0.28756 (5) | 0.1579 (2) | −0.12085 (10) | 0.0607 (6) | |
C6 | −0.31732 (9) | 0.1037 (4) | −0.18819 (16) | 0.0685 (10) | |
H6A | −0.3450 | 0.1253 | −0.2018 | 0.103* | |
H6B | −0.3143 | 0.0168 | −0.1846 | 0.103* | |
H6C | −0.3124 | 0.1328 | −0.2229 | 0.103* | |
C11 | −0.21310 (8) | −0.3037 (3) | −0.15058 (16) | 0.0593 (8) | |
C12 | −0.23658 (11) | −0.3041 (4) | −0.22965 (18) | 0.0845 (12) | |
H12A | −0.2172 | −0.2990 | −0.2439 | 0.127* | |
H12B | −0.2551 | −0.2357 | −0.2480 | 0.127* | |
H12C | −0.2524 | −0.3779 | −0.2475 | 0.127* | |
C13 | −0.18066 (11) | −0.3998 (3) | −0.1175 (2) | 0.0825 (12) | |
H13A | −0.1623 | −0.3925 | −0.1337 | 0.124* | |
H13B | −0.1937 | −0.4783 | −0.1301 | 0.124* | |
H13C | −0.1650 | −0.3907 | −0.0672 | 0.124* | |
C14 | −0.24257 (10) | −0.3125 (4) | −0.1256 (2) | 0.0881 (12) | |
H14A | −0.2630 | −0.2492 | −0.1471 | 0.132* | |
H14B | −0.2271 | −0.3038 | −0.0753 | 0.132* | |
H14C | −0.2562 | −0.3902 | −0.1386 | 0.132* | |
C15 | −0.16552 (7) | −0.1358 (3) | −0.13432 (13) | 0.0458 (7) | |
O11" | −0.19436 (6) | −0.18327 (19) | −0.12436 (11) | 0.0593 (5) | |
O15" | −0.14846 (6) | −0.1896 (2) | −0.15847 (12) | 0.0658 (6) | |
N11 | −0.15887 (7) | −0.0206 (2) | −0.11335 (13) | 0.0573 (6) | |
H11A | −0.1732 | 0.0079 | −0.0978 | 0.069* | |
C11A | −0.12971 (7) | 0.0613 (3) | −0.11431 (14) | 0.0471 (6) | |
H11B | −0.1120 | 0.0164 | −0.1255 | 0.056* | |
C11B | −0.15384 (8) | 0.1604 (3) | −0.16950 (15) | 0.0558 (8) | |
H11C | −0.1689 | 0.1227 | −0.2157 | 0.067* | |
H11D | −0.1743 | 0.1946 | −0.1617 | 0.067* | |
C11G | −0.12814 (8) | 0.2621 (3) | −0.17019 (14) | 0.0526 (7) | |
C11D | −0.11808 (9) | 0.3615 (3) | −0.12645 (16) | 0.0603 (8) | |
H11E | −0.1271 | 0.3632 | −0.0959 | 0.072* | |
C11E | −0.09502 (9) | 0.4590 (3) | −0.12637 (17) | 0.0677 (9) | |
H11F | −0.0889 | 0.5245 | −0.0963 | 0.081* | |
C11Z | −0.08132 (9) | 0.4578 (4) | −0.17132 (19) | 0.0753 (10) | |
O11Z | −0.06014 (8) | 0.5521 (3) | −0.17546 (16) | 0.1056 (9) | |
H11G | −0.0626 | 0.6120 | −0.1565 | 0.158* | |
C11Y | −0.09007 (10) | 0.3578 (4) | −0.21446 (19) | 0.0783 (10) | |
H11H | −0.0803 | 0.3556 | −0.2440 | 0.094* | |
C11X | −0.11306 (9) | 0.2614 (3) | −0.21410 (16) | 0.0663 (9) | |
H11I | −0.1186 | 0.1951 | −0.2434 | 0.080* | |
C11' | −0.10328 (7) | 0.1163 (3) | −0.04072 (12) | 0.0445 (6) | |
O11 | −0.12059 (5) | 0.16162 (19) | −0.01381 (10) | 0.0547 (5) | |
N12 | −0.06212 (6) | 0.1100 (3) | −0.00834 (11) | 0.0610 (7) | |
H12D | −0.0513 | 0.0792 | −0.0296 | 0.073* | |
C12A | −0.03522 (8) | 0.1561 (4) | 0.06392 (14) | 0.0752 (11) | |
H12E | −0.0514 | 0.1580 | 0.0855 | 0.090* | |
C12B | −0.01902 (12) | 0.2821 (5) | 0.0671 (2) | 0.1023 (15) | |
H12F | −0.0420 | 0.3369 | 0.0408 | 0.153* | |
H12G | −0.0024 | 0.2814 | 0.0473 | 0.153* | |
H12H | −0.0023 | 0.3084 | 0.1152 | 0.153* | |
C12' | 0.00076 (8) | 0.0665 (4) | 0.10518 (15) | 0.0777 (12) | |
O12 | 0.02313 (6) | 0.0338 (4) | 0.08436 (12) | 0.1115 (13) | |
N13 | 0.00695 (7) | 0.0305 (3) | 0.16498 (12) | 0.0633 (7) | |
H13D | −0.0112 | 0.0487 | 0.1747 | 0.076* | |
C13A | 0.04303 (9) | −0.0385 (4) | 0.21522 (15) | 0.0667 (9) | |
H13E | 0.0611 | −0.0490 | 0.1981 | 0.080* | |
H13F | 0.0345 | −0.1183 | 0.2208 | 0.080* | |
C13' | 0.06648 (7) | 0.0257 (3) | 0.28538 (13) | 0.0462 (6) | |
O13 | 0.04815 (5) | 0.0965 (2) | 0.30163 (9) | 0.0540 (5) | |
N14 | 0.10714 (6) | −0.0022 (2) | 0.32794 (10) | 0.0425 (5) | |
C14N | 0.12804 (8) | −0.0871 (3) | 0.30748 (14) | 0.0539 (7) | |
H14D | 0.1282 | −0.0543 | 0.2684 | 0.081* | |
H14E | 0.1135 | −0.1634 | 0.2942 | 0.081* | |
H14F | 0.1562 | −0.0994 | 0.3465 | 0.081* | |
C14A | 0.12988 (7) | 0.0438 (2) | 0.40005 (12) | 0.0412 (6) | |
H14G | 0.1099 | 0.0880 | 0.4061 | 0.049* | |
C14B | 0.14791 (7) | −0.0593 (3) | 0.45453 (13) | 0.0467 (6) | |
H14H | 0.1693 | −0.1015 | 0.4522 | 0.056* | |
H14I | 0.1607 | −0.0252 | 0.5014 | 0.056* | |
C14G | 0.11449 (7) | −0.1486 (2) | 0.44152 (13) | 0.0452 (6) | |
C14D | 0.11486 (9) | −0.2675 (3) | 0.42242 (18) | 0.0658 (8) | |
H14J | 0.1368 | −0.2943 | 0.4192 | 0.079* | |
C14E | 0.08331 (11) | −0.3480 (3) | 0.4079 (2) | 0.0782 (10) | |
H14K | 0.0842 | −0.4277 | 0.3952 | 0.094* | |
C14Z | 0.05080 (9) | −0.3103 (3) | 0.41233 (17) | 0.0645 (8) | |
H14L | 0.0292 | −0.3634 | 0.4014 | 0.077* | |
C14Y | 0.05049 (9) | −0.1939 (3) | 0.43294 (16) | 0.0597 (8) | |
H14M | 0.0288 | −0.1685 | 0.4372 | 0.072* | |
C14X | 0.08194 (8) | −0.1132 (3) | 0.44764 (14) | 0.0536 (7) | |
H14N | 0.0812 | −0.0344 | 0.4618 | 0.064* | |
C14' | 0.16399 (7) | 0.1343 (2) | 0.41393 (12) | 0.0411 (6) | |
O14 | 0.18350 (5) | 0.12637 (19) | 0.38582 (10) | 0.0574 (5) | |
N15 | 0.17164 (6) | 0.2185 (2) | 0.46196 (11) | 0.0459 (5) | |
H15A | 0.1564 | 0.2187 | 0.4791 | 0.055* | |
C15A | 0.20394 (7) | 0.3092 (2) | 0.48691 (13) | 0.0439 (6) | |
H15B | 0.2260 | 0.2764 | 0.4821 | 0.053* | |
C15B | 0.18708 (8) | 0.4262 (3) | 0.44207 (14) | 0.0520 (7) | |
H15C | 0.1675 | 0.4034 | 0.3933 | 0.062* | |
H15D | 0.1719 | 0.4726 | 0.4574 | 0.062* | |
C15G | 0.22023 (8) | 0.5072 (3) | 0.44589 (16) | 0.0603 (8) | |
H15E | 0.2356 | 0.4607 | 0.4310 | 0.072* | |
H15F | 0.2396 | 0.5308 | 0.4945 | 0.072* | |
S15 | 0.20030 (2) | 0.64239 (7) | 0.39285 (4) | 0.0635 (2) | |
C15D | 0.17037 (19) | 0.5858 (5) | 0.3073 (2) | 0.139 (2) | |
H15G | 0.1581 | 0.6522 | 0.2747 | 0.208* | |
H15H | 0.1487 | 0.5347 | 0.3028 | 0.208* | |
H15I | 0.1878 | 0.5394 | 0.2974 | 0.208* | |
C15' | 0.22198 (7) | 0.3297 (2) | 0.56408 (13) | 0.0431 (6) | |
O15 | 0.21183 (5) | 0.2769 (2) | 0.59850 (10) | 0.0594 (5) | |
O15' | 0.25061 (5) | 0.41852 (18) | 0.58982 (9) | 0.0523 (5) | |
C16 | 0.26957 (8) | 0.4467 (3) | 0.66293 (14) | 0.0561 (7) | |
H16A | 0.2895 | 0.5108 | 0.6761 | 0.084* | |
H16B | 0.2834 | 0.3758 | 0.6908 | 0.084* | |
H16C | 0.2485 | 0.4725 | 0.6708 | 0.084* | |
O1S | 0.05487 (6) | 0.8813 (2) | 0.57992 (12) | 0.0665 (6) | |
H1SA | 0.0421 (9) | 0.947 (4) | 0.5748 (19) | 0.093* | |
H1SB | 0.0802 (10) | 0.896 (4) | 0.5936 (19) | 0.093* | |
O2S | −0.06536 (8) | −0.2403 (3) | −0.11361 (19) | 0.1077 (10) | |
H2SA | −0.0911 (5) | −0.221 (4) | −0.126 (2) | 0.151* | |
H2SB | −0.0487 (9) | −0.182 (3) | −0.086 (2) | 0.151* | |
O3S | 0.0078 (4) | −0.1467 (10) | 0.0000 (8) | 0.104 (4)* | 0.25 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0497 (12) | 0.0451 (16) | 0.0807 (18) | 0.0104 (13) | 0.0328 (12) | 0.0204 (13) |
C2 | 0.0739 (18) | 0.0463 (18) | 0.076 (2) | 0.0018 (16) | 0.0326 (15) | 0.0068 (14) |
C3 | 0.0848 (18) | 0.071 (2) | 0.167 (3) | 0.0409 (18) | 0.0841 (19) | 0.052 (2) |
C4 | 0.0688 (18) | 0.063 (2) | 0.065 (2) | −0.0059 (18) | 0.0102 (15) | 0.0215 (16) |
C5 | 0.0362 (10) | 0.0476 (15) | 0.0404 (12) | 0.0053 (11) | 0.0180 (8) | 0.0067 (10) |
O0 | 0.0548 (8) | 0.0592 (12) | 0.0664 (10) | 0.0063 (9) | 0.0392 (7) | 0.0179 (8) |
O | 0.0466 (8) | 0.0464 (11) | 0.0681 (10) | 0.0116 (8) | 0.0347 (7) | 0.0176 (8) |
N1 | 0.0376 (8) | 0.0437 (12) | 0.0496 (10) | 0.0066 (9) | 0.0256 (7) | 0.0091 (8) |
C1A | 0.0343 (9) | 0.0418 (14) | 0.0414 (12) | 0.0015 (10) | 0.0196 (8) | 0.0005 (9) |
C1B | 0.0343 (10) | 0.0677 (19) | 0.0426 (13) | −0.0010 (12) | 0.0144 (9) | −0.0086 (12) |
C1G | 0.0350 (10) | 0.0520 (16) | 0.0448 (12) | −0.0059 (11) | 0.0181 (9) | −0.0151 (11) |
C1D1 | 0.0448 (11) | 0.0553 (17) | 0.0452 (13) | −0.0051 (12) | 0.0213 (10) | −0.0062 (11) |
C1E1 | 0.0500 (11) | 0.0608 (18) | 0.0564 (14) | −0.0075 (13) | 0.0327 (10) | −0.0105 (12) |
C1Z | 0.0420 (11) | 0.0509 (16) | 0.0602 (15) | −0.0062 (12) | 0.0264 (10) | −0.0157 (12) |
O1Z | 0.0664 (9) | 0.0559 (12) | 0.0872 (12) | 0.0055 (10) | 0.0502 (9) | −0.0106 (9) |
C1E2 | 0.0594 (13) | 0.0518 (16) | 0.0556 (15) | −0.0009 (13) | 0.0321 (11) | −0.0056 (12) |
C1D2 | 0.0559 (12) | 0.0513 (16) | 0.0526 (13) | −0.0047 (13) | 0.0321 (10) | −0.0114 (11) |
C1' | 0.0333 (9) | 0.0315 (12) | 0.0420 (11) | −0.0001 (10) | 0.0187 (8) | −0.0042 (9) |
O1 | 0.0353 (7) | 0.0606 (11) | 0.0455 (8) | −0.0046 (8) | 0.0231 (6) | 0.0047 (7) |
N2 | 0.0331 (8) | 0.0415 (11) | 0.0344 (9) | −0.0035 (8) | 0.0174 (7) | 0.0007 (8) |
C2A | 0.0318 (10) | 0.0470 (15) | 0.0366 (12) | −0.0025 (10) | 0.0141 (8) | 0.0033 (10) |
C2B | 0.0523 (15) | 0.0497 (18) | 0.0628 (18) | −0.0027 (14) | 0.0121 (13) | 0.0091 (14) |
C2' | 0.0325 (9) | 0.0419 (13) | 0.0349 (11) | −0.0003 (10) | 0.0164 (8) | 0.0010 (9) |
O2 | 0.0436 (7) | 0.0587 (11) | 0.0423 (8) | −0.0123 (8) | 0.0273 (6) | −0.0100 (7) |
N3 | 0.0430 (8) | 0.0669 (15) | 0.0392 (10) | −0.0179 (10) | 0.0247 (7) | −0.0105 (9) |
C3A | 0.0526 (12) | 0.079 (2) | 0.0433 (13) | −0.0257 (14) | 0.0276 (10) | −0.0108 (12) |
C3' | 0.0384 (10) | 0.0471 (15) | 0.0396 (11) | −0.0024 (11) | 0.0211 (8) | −0.0034 (10) |
O3 | 0.0391 (7) | 0.0670 (12) | 0.0404 (8) | −0.0127 (8) | 0.0218 (6) | −0.0029 (7) |
N4 | 0.0357 (8) | 0.0506 (13) | 0.0411 (10) | −0.0071 (9) | 0.0217 (7) | −0.0037 (8) |
C4N | 0.0556 (12) | 0.0654 (19) | 0.0572 (14) | −0.0201 (13) | 0.0363 (10) | −0.0117 (12) |
C4A | 0.0339 (9) | 0.0533 (16) | 0.0382 (12) | −0.0036 (11) | 0.0180 (8) | 0.0017 (10) |
C4B | 0.0432 (11) | 0.0580 (17) | 0.0396 (13) | −0.0042 (13) | 0.0173 (9) | −0.0043 (11) |
C4G | 0.0494 (12) | 0.0526 (17) | 0.0612 (15) | −0.0067 (12) | 0.0326 (11) | −0.0112 (12) |
C4D1 | 0.0526 (13) | 0.0512 (17) | 0.0637 (16) | 0.0039 (13) | 0.0317 (11) | 0.0037 (12) |
C4E1 | 0.0525 (14) | 0.076 (2) | 0.081 (2) | 0.0077 (16) | 0.0320 (14) | 0.0068 (16) |
C4Z | 0.0561 (15) | 0.082 (3) | 0.109 (3) | 0.0117 (18) | 0.0427 (16) | 0.005 (2) |
C4E2 | 0.0755 (15) | 0.103 (3) | 0.115 (2) | −0.003 (2) | 0.0722 (15) | −0.016 (2) |
C4D2 | 0.0715 (16) | 0.087 (3) | 0.0684 (18) | 0.0020 (17) | 0.0439 (13) | −0.0069 (16) |
C4' | 0.0375 (10) | 0.0564 (17) | 0.0468 (13) | −0.0052 (12) | 0.0190 (9) | 0.0000 (11) |
O4 | 0.0406 (9) | 0.0968 (17) | 0.1152 (16) | 0.0068 (11) | 0.0384 (10) | 0.0476 (13) |
N5 | 0.0334 (8) | 0.0548 (14) | 0.0493 (11) | 0.0028 (10) | 0.0207 (7) | 0.0070 (9) |
C5A | 0.0369 (10) | 0.0542 (16) | 0.0498 (13) | 0.0043 (12) | 0.0221 (9) | 0.0010 (11) |
C5B | 0.0465 (12) | 0.0480 (16) | 0.0565 (15) | 0.0032 (13) | 0.0234 (10) | −0.0024 (12) |
C5G | 0.065 (3) | 0.063 (4) | 0.065 (3) | −0.025 (3) | 0.039 (2) | −0.024 (2) |
S5 | 0.0606 (6) | 0.0480 (7) | 0.0737 (7) | −0.0073 (6) | 0.0345 (5) | −0.0152 (5) |
C5D | 0.046 (3) | 0.125 (7) | 0.158 (6) | −0.013 (4) | 0.038 (4) | −0.078 (5) |
C5G' | 0.078 (5) | 0.073 (8) | 0.111 (7) | 0.008 (5) | 0.068 (5) | −0.014 (6) |
S5' | 0.1018 (18) | 0.114 (2) | 0.0623 (15) | 0.0175 (17) | 0.0175 (12) | −0.0227 (14) |
C5D' | 0.067 (4) | 0.063 (5) | 0.073 (4) | −0.004 (4) | 0.033 (3) | −0.018 (4) |
C5' | 0.0405 (10) | 0.0408 (14) | 0.0488 (13) | −0.0007 (11) | 0.0219 (9) | 0.0038 (11) |
O5 | 0.0499 (9) | 0.0799 (15) | 0.0561 (10) | 0.0055 (10) | 0.0263 (8) | −0.0118 (10) |
O5' | 0.0335 (7) | 0.0762 (15) | 0.0610 (11) | 0.0016 (9) | 0.0185 (7) | −0.0080 (10) |
C6 | 0.0458 (13) | 0.081 (2) | 0.0614 (18) | −0.0051 (16) | 0.0180 (12) | −0.0042 (16) |
C11 | 0.0490 (13) | 0.0473 (17) | 0.0641 (17) | −0.0096 (14) | 0.0198 (12) | 0.0007 (13) |
C12 | 0.0755 (19) | 0.073 (2) | 0.068 (2) | −0.0311 (19) | 0.0158 (16) | 0.0032 (18) |
C13 | 0.0744 (19) | 0.059 (2) | 0.091 (2) | −0.0010 (19) | 0.0304 (17) | 0.0123 (18) |
C14 | 0.0788 (18) | 0.082 (3) | 0.112 (3) | −0.029 (2) | 0.0580 (17) | −0.006 (2) |
C15 | 0.0368 (11) | 0.0464 (15) | 0.0462 (13) | −0.0036 (11) | 0.0175 (9) | −0.0030 (10) |
O11" | 0.0555 (9) | 0.0504 (12) | 0.0783 (11) | −0.0111 (9) | 0.0405 (8) | −0.0085 (9) |
O15" | 0.0611 (9) | 0.0633 (13) | 0.0837 (12) | −0.0094 (10) | 0.0464 (9) | −0.0193 (10) |
N11 | 0.0538 (10) | 0.0498 (14) | 0.0825 (13) | −0.0127 (11) | 0.0465 (9) | −0.0174 (10) |
C11A | 0.0375 (10) | 0.0481 (16) | 0.0528 (13) | −0.0051 (11) | 0.0229 (9) | −0.0049 (11) |
C11B | 0.0443 (12) | 0.0615 (19) | 0.0473 (14) | −0.0048 (13) | 0.0158 (10) | −0.0076 (12) |
C11G | 0.0444 (12) | 0.0595 (18) | 0.0491 (14) | −0.0002 (13) | 0.0225 (10) | −0.0016 (12) |
C11D | 0.0629 (14) | 0.065 (2) | 0.0602 (16) | −0.0065 (15) | 0.0380 (12) | 0.0010 (13) |
C11E | 0.0648 (14) | 0.069 (2) | 0.0765 (18) | −0.0105 (16) | 0.0435 (13) | −0.0003 (15) |
C11Z | 0.0582 (14) | 0.080 (2) | 0.092 (2) | −0.0024 (17) | 0.0444 (14) | 0.0161 (18) |
O11Z | 0.0949 (12) | 0.102 (2) | 0.153 (2) | −0.0208 (15) | 0.0891 (13) | 0.0091 (16) |
C11Y | 0.0799 (16) | 0.094 (3) | 0.0863 (19) | 0.0083 (19) | 0.0616 (14) | 0.0134 (17) |
C11X | 0.0670 (15) | 0.074 (2) | 0.0597 (17) | 0.0124 (16) | 0.0357 (13) | 0.0021 (14) |
C11' | 0.0415 (10) | 0.0485 (16) | 0.0442 (12) | −0.0053 (11) | 0.0240 (9) | 0.0019 (10) |
O11 | 0.0467 (8) | 0.0674 (13) | 0.0580 (10) | −0.0051 (9) | 0.0337 (7) | −0.0091 (8) |
N12 | 0.0372 (9) | 0.108 (2) | 0.0385 (11) | −0.0071 (12) | 0.0212 (8) | −0.0045 (11) |
C12A | 0.0474 (12) | 0.144 (4) | 0.0367 (14) | −0.0155 (18) | 0.0250 (10) | −0.0124 (16) |
C12B | 0.083 (2) | 0.151 (4) | 0.060 (2) | −0.044 (3) | 0.0307 (16) | −0.032 (2) |
C12' | 0.0366 (11) | 0.157 (4) | 0.0412 (14) | −0.0136 (18) | 0.0222 (10) | −0.0093 (17) |
O12 | 0.0549 (10) | 0.237 (4) | 0.0574 (12) | 0.0148 (17) | 0.0399 (9) | 0.0069 (16) |
N13 | 0.0428 (9) | 0.109 (2) | 0.0407 (11) | −0.0111 (13) | 0.0248 (8) | −0.0140 (12) |
C13A | 0.0538 (13) | 0.092 (2) | 0.0517 (15) | −0.0052 (16) | 0.0268 (11) | −0.0191 (15) |
C13' | 0.0425 (10) | 0.0571 (17) | 0.0433 (12) | −0.0070 (12) | 0.0262 (9) | −0.0032 (11) |
O13 | 0.0408 (7) | 0.0745 (14) | 0.0451 (9) | 0.0034 (9) | 0.0224 (6) | −0.0067 (8) |
N14 | 0.0412 (8) | 0.0475 (13) | 0.0427 (10) | −0.0018 (9) | 0.0254 (7) | −0.0006 (8) |
C14N | 0.0532 (12) | 0.0547 (17) | 0.0584 (15) | −0.0005 (13) | 0.0334 (11) | −0.0098 (12) |
C14A | 0.0430 (10) | 0.0413 (14) | 0.0407 (12) | −0.0020 (11) | 0.0238 (9) | −0.0015 (10) |
C14B | 0.0413 (10) | 0.0494 (16) | 0.0469 (13) | 0.0015 (12) | 0.0224 (9) | 0.0060 (11) |
C14G | 0.0455 (11) | 0.0435 (15) | 0.0457 (13) | 0.0023 (11) | 0.0244 (9) | 0.0070 (10) |
C14D | 0.0701 (14) | 0.0474 (18) | 0.097 (2) | 0.0023 (14) | 0.0565 (14) | 0.0001 (14) |
C14E | 0.0955 (19) | 0.0431 (18) | 0.114 (2) | −0.0129 (17) | 0.0689 (17) | −0.0102 (16) |
C14Z | 0.0637 (14) | 0.0531 (18) | 0.0814 (18) | −0.0157 (15) | 0.0427 (13) | −0.0020 (14) |
C14Y | 0.0564 (13) | 0.0614 (19) | 0.0716 (16) | −0.0046 (14) | 0.0417 (12) | 0.0035 (13) |
C14X | 0.0581 (13) | 0.0508 (17) | 0.0591 (15) | −0.0022 (13) | 0.0367 (11) | −0.0029 (12) |
C14' | 0.0349 (9) | 0.0452 (14) | 0.0418 (12) | 0.0001 (11) | 0.0201 (8) | 0.0014 (10) |
O14 | 0.0564 (8) | 0.0612 (12) | 0.0707 (10) | −0.0118 (9) | 0.0451 (7) | −0.0164 (9) |
N15 | 0.0473 (9) | 0.0459 (13) | 0.0530 (11) | −0.0085 (10) | 0.0328 (8) | −0.0032 (9) |
C15A | 0.0408 (10) | 0.0451 (15) | 0.0467 (13) | −0.0059 (11) | 0.0246 (9) | −0.0045 (10) |
C15B | 0.0427 (11) | 0.0565 (17) | 0.0531 (14) | −0.0012 (13) | 0.0239 (10) | 0.0033 (12) |
C15G | 0.0521 (13) | 0.064 (2) | 0.0593 (16) | −0.0097 (14) | 0.0270 (11) | 0.0063 (14) |
S15 | 0.0647 (4) | 0.0525 (4) | 0.0719 (4) | −0.0033 (4) | 0.0365 (3) | 0.0092 (3) |
C15D | 0.220 (6) | 0.080 (3) | 0.070 (3) | −0.023 (4) | 0.049 (3) | 0.016 (2) |
C15' | 0.0361 (10) | 0.0425 (14) | 0.0504 (13) | −0.0001 (11) | 0.0233 (9) | 0.0013 (10) |
O15 | 0.0495 (8) | 0.0762 (14) | 0.0557 (10) | −0.0175 (10) | 0.0309 (7) | −0.0015 (9) |
O15' | 0.0577 (9) | 0.0495 (11) | 0.0489 (9) | −0.0131 (9) | 0.0287 (7) | −0.0058 (8) |
C16 | 0.0556 (13) | 0.0618 (19) | 0.0480 (14) | −0.0112 (14) | 0.0265 (11) | −0.0100 (12) |
O1S | 0.0653 (10) | 0.0568 (13) | 0.0840 (12) | 0.0022 (10) | 0.0449 (9) | −0.0121 (10) |
O2S | 0.0823 (13) | 0.0830 (19) | 0.172 (2) | 0.0008 (15) | 0.0784 (15) | 0.0180 (17) |
C1—O | 1.474 (3) | C6—H6C | 0.9600 |
C1—C2 | 1.499 (4) | C11—O11" | 1.469 (4) |
C1—C3 | 1.508 (5) | C11—C13 | 1.486 (5) |
C1—C4 | 1.521 (5) | C11—C12 | 1.504 (5) |
C2—H2A | 0.9600 | C11—C14 | 1.520 (5) |
C2—H2B | 0.9600 | C12—H12A | 0.9600 |
C2—H2C | 0.9600 | C12—H12B | 0.9600 |
C3—H3A | 0.9600 | C12—H12C | 0.9600 |
C3—H3B | 0.9600 | C13—H13A | 0.9600 |
C3—H3C | 0.9600 | C13—H13B | 0.9600 |
C4—H4A | 0.9600 | C13—H13C | 0.9600 |
C4—H4B | 0.9600 | C14—H14A | 0.9600 |
C4—H4C | 0.9600 | C14—H14B | 0.9600 |
C5—O0 | 1.220 (3) | C14—H14C | 0.9600 |
C5—N1 | 1.335 (3) | C15—O15" | 1.213 (4) |
C5—O | 1.339 (3) | C15—N11 | 1.329 (4) |
N1—C1A | 1.460 (3) | C15—O11" | 1.349 (3) |
N1—H1A | 0.8600 | N11—C11A | 1.446 (4) |
C1A—C1' | 1.528 (3) | N11—H11A | 0.8600 |
C1A—C1B | 1.529 (4) | C11A—C11' | 1.527 (4) |
C1A—H1AA | 0.9800 | C11A—C11B | 1.531 (4) |
C1B—C1G | 1.501 (4) | C11A—H11B | 0.9800 |
C1B—H1BA | 0.9700 | C11B—C11G | 1.497 (4) |
C1B—H1BB | 0.9700 | C11B—H11C | 0.9700 |
C1G—C1D2 | 1.389 (4) | C11B—H11D | 0.9700 |
C1G—C1D1 | 1.399 (4) | C11G—C11D | 1.382 (4) |
C1D1—C1E1 | 1.371 (4) | C11G—C11X | 1.399 (5) |
C1D1—H1DA | 0.9300 | C11D—C11E | 1.390 (5) |
C1E1—C1Z | 1.385 (4) | C11D—H11E | 0.9300 |
C1E1—H1EA | 0.9300 | C11E—C11Z | 1.379 (5) |
C1Z—O1Z | 1.358 (3) | C11E—H11F | 0.9300 |
C1Z—C1E2 | 1.388 (4) | C11Z—O11Z | 1.352 (4) |
O1Z—H1ZA | 0.8200 | C11Z—C11Y | 1.387 (6) |
C1E2—C1D2 | 1.376 (4) | O11Z—H11G | 0.8200 |
C1E2—H1EB | 0.9300 | C11Y—C11X | 1.382 (5) |
C1D2—H1DB | 0.9300 | C11Y—H11H | 0.9300 |
C1'—O1 | 1.236 (3) | C11X—H11I | 0.9300 |
C1'—N2 | 1.325 (3) | C11'—O11 | 1.227 (3) |
N2—C2A | 1.461 (3) | C11'—N12 | 1.330 (3) |
N2—H2D | 0.8600 | N12—C12A | 1.469 (4) |
C2A—C2' | 1.515 (3) | N12—H12D | 0.8600 |
C2A—C2B | 1.517 (4) | C12A—C12B | 1.505 (7) |
C2A—H2AA | 0.9800 | C12A—C12' | 1.529 (5) |
C2B—H2BA | 0.9600 | C12A—H12E | 0.9800 |
C2B—H2BB | 0.9600 | C12B—H12F | 0.9600 |
C2B—H2BC | 0.9600 | C12B—H12G | 0.9600 |
C2'—O2 | 1.235 (3) | C12B—H12H | 0.9600 |
C2'—N3 | 1.318 (3) | C12'—O12 | 1.238 (4) |
N3—C3A | 1.451 (3) | C12'—N13 | 1.305 (4) |
N3—H3D | 0.8600 | N13—C13A | 1.437 (4) |
C3A—C3' | 1.504 (4) | N13—H13D | 0.8600 |
C3A—H3AA | 0.9700 | C13A—C13' | 1.509 (4) |
C3A—H3AB | 0.9700 | C13A—H13E | 0.9700 |
C3'—O3 | 1.233 (3) | C13A—H13F | 0.9700 |
C3'—N4 | 1.346 (3) | C13'—O13 | 1.233 (3) |
N4—C4A | 1.463 (3) | C13'—N14 | 1.346 (3) |
N4—C4N | 1.472 (3) | N14—C14A | 1.461 (3) |
C4N—H4NA | 0.9600 | N14—C14N | 1.462 (4) |
C4N—H4NB | 0.9600 | C14N—H14D | 0.9600 |
C4N—H4NC | 0.9600 | C14N—H14E | 0.9600 |
C4A—C4B | 1.526 (4) | C14N—H14F | 0.9600 |
C4A—C4' | 1.527 (3) | C14A—C14' | 1.533 (3) |
C4A—H4AA | 0.9800 | C14A—C14B | 1.536 (4) |
C4B—C4G | 1.505 (4) | C14A—H14G | 0.9800 |
C4B—H4BA | 0.9700 | C14B—C14G | 1.510 (4) |
C4B—H4BB | 0.9700 | C14B—H14H | 0.9700 |
C4G—C4D1 | 1.386 (4) | C14B—H14I | 0.9700 |
C4G—C4D2 | 1.392 (5) | C14G—C14D | 1.381 (4) |
C4D1—C4E1 | 1.373 (4) | C14G—C14X | 1.385 (4) |
C4D1—H4DA | 0.9300 | C14D—C14E | 1.386 (5) |
C4E1—C4Z | 1.368 (6) | C14D—H14J | 0.9300 |
C4E1—H4EA | 0.9300 | C14E—C14Z | 1.368 (5) |
C4Z—C4E2 | 1.377 (5) | C14E—H14K | 0.9300 |
C4Z—H4ZA | 0.9300 | C14Z—C14Y | 1.365 (5) |
C4E2—C4D2 | 1.397 (5) | C14Z—H14L | 0.9300 |
C4E2—H4EB | 0.9300 | C14Y—C14X | 1.383 (4) |
C4D2—H4DB | 0.9300 | C14Y—H14M | 0.9300 |
C4'—O4 | 1.226 (3) | C14X—H14N | 0.9300 |
C4'—N5 | 1.319 (4) | C14'—O14 | 1.223 (3) |
N5—C5A | 1.442 (3) | C14'—N15 | 1.335 (3) |
N5—H5A | 0.8600 | N15—C15A | 1.444 (3) |
C5A—C5' | 1.516 (4) | N15—H15A | 0.8600 |
C5A—C5B | 1.522 (4) | C15A—C15' | 1.507 (4) |
C5A—H5AA | 0.9800 | C15A—C15B | 1.546 (4) |
C5B—C5G' | 1.503 (13) | C15A—H15B | 0.9800 |
C5B—C5G | 1.574 (8) | C15B—C15G | 1.516 (4) |
C5B—H5BA | 0.9700 | C15B—H15C | 0.9700 |
C5B—H5BB | 0.9700 | C15B—H15D | 0.9700 |
C5G—S5 | 1.837 (7) | C15G—S15 | 1.799 (3) |
C5G—H5GA | 0.9700 | C15G—H15E | 0.9700 |
C5G—H5GB | 0.9700 | C15G—H15F | 0.9700 |
S5—C5D | 1.920 (9) | S15—C15D | 1.742 (5) |
C5D—H5DA | 0.9600 | C15D—H15G | 0.9600 |
C5D—H5DB | 0.9600 | C15D—H15H | 0.9600 |
C5D—H5DC | 0.9600 | C15D—H15I | 0.9600 |
C5G'—S5' | 1.678 (12) | C15'—O15 | 1.196 (3) |
C5G'—H5GC | 0.9700 | C15'—O15' | 1.342 (3) |
C5G'—H5GD | 0.9700 | O15'—C16 | 1.434 (3) |
S5'—C5D' | 1.896 (15) | C16—H16A | 0.9600 |
C5D'—H5DD | 0.9600 | C16—H16B | 0.9600 |
C5D'—H5DE | 0.9600 | C16—H16C | 0.9600 |
C5D'—H5DF | 0.9600 | O1S—H1SA | 0.85 (4) |
C5'—O5 | 1.203 (3) | O1S—H1SB | 0.86 (3) |
C5'—O5' | 1.311 (3) | O2S—H2SA | 0.893 (17) |
O5'—C6 | 1.444 (4) | O2S—H2SB | 0.874 (18) |
C6—H6A | 0.9600 | O3S—O3Si | 0.60 (3) |
C6—H6B | 0.9600 | ||
O—C1—C2 | 111.2 (2) | C5'—O5'—C6 | 117.0 (2) |
O—C1—C3 | 102.1 (3) | O5'—C6—H6A | 109.5 |
C2—C1—C3 | 111.1 (3) | O5'—C6—H6B | 109.5 |
O—C1—C4 | 108.5 (3) | H6A—C6—H6B | 109.5 |
C2—C1—C4 | 112.6 (3) | O5'—C6—H6C | 109.5 |
C3—C1—C4 | 110.8 (3) | H6A—C6—H6C | 109.5 |
C1—C2—H2A | 109.5 | H6B—C6—H6C | 109.5 |
C1—C2—H2B | 109.5 | O11"—C11—C13 | 110.4 (2) |
H2A—C2—H2B | 109.5 | O11"—C11—C12 | 109.1 (3) |
C1—C2—H2C | 109.5 | C13—C11—C12 | 113.0 (3) |
H2A—C2—H2C | 109.5 | O11"—C11—C14 | 101.9 (3) |
H2B—C2—H2C | 109.5 | C13—C11—C14 | 110.7 (3) |
C1—C3—H3A | 109.5 | C12—C11—C14 | 111.3 (3) |
C1—C3—H3B | 109.5 | C11—C12—H12A | 109.5 |
H3A—C3—H3B | 109.5 | C11—C12—H12B | 109.5 |
C1—C3—H3C | 109.5 | H12A—C12—H12B | 109.5 |
H3A—C3—H3C | 109.5 | C11—C12—H12C | 109.5 |
H3B—C3—H3C | 109.5 | H12A—C12—H12C | 109.5 |
C1—C4—H4A | 109.5 | H12B—C12—H12C | 109.5 |
C1—C4—H4B | 109.5 | C11—C13—H13A | 109.5 |
H4A—C4—H4B | 109.5 | C11—C13—H13B | 109.5 |
C1—C4—H4C | 109.5 | H13A—C13—H13B | 109.5 |
H4A—C4—H4C | 109.5 | C11—C13—H13C | 109.5 |
H4B—C4—H4C | 109.5 | H13A—C13—H13C | 109.5 |
O0—C5—N1 | 124.6 (2) | H13B—C13—H13C | 109.5 |
O0—C5—O | 125.2 (2) | C11—C14—H14A | 109.5 |
N1—C5—O | 110.2 (2) | C11—C14—H14B | 109.5 |
C5—O—C1 | 121.9 (2) | H14A—C14—H14B | 109.5 |
C5—N1—C1A | 124.1 (2) | C11—C14—H14C | 109.5 |
C5—N1—H1A | 118.0 | H14A—C14—H14C | 109.5 |
C1A—N1—H1A | 118.0 | H14B—C14—H14C | 109.5 |
N1—C1A—C1' | 106.8 (2) | O15"—C15—N11 | 125.6 (3) |
N1—C1A—C1B | 109.07 (18) | O15"—C15—O11" | 125.5 (3) |
C1'—C1A—C1B | 112.0 (2) | N11—C15—O11" | 108.9 (2) |
N1—C1A—H1AA | 109.6 | C15—O11"—C11 | 123.1 (2) |
C1'—C1A—H1AA | 109.6 | C15—N11—C11A | 126.0 (3) |
C1B—C1A—H1AA | 109.6 | C15—N11—H11A | 117.0 |
C1G—C1B—C1A | 116.52 (19) | C11A—N11—H11A | 117.0 |
C1G—C1B—H1BA | 108.2 | N11—C11A—C11' | 106.7 (2) |
C1A—C1B—H1BA | 108.2 | N11—C11A—C11B | 109.2 (2) |
C1G—C1B—H1BB | 108.2 | C11'—C11A—C11B | 110.8 (2) |
C1A—C1B—H1BB | 108.2 | N11—C11A—H11B | 110.0 |
H1BA—C1B—H1BB | 107.3 | C11'—C11A—H11B | 110.0 |
C1D2—C1G—C1D1 | 117.0 (3) | C11B—C11A—H11B | 110.0 |
C1D2—C1G—C1B | 121.4 (3) | C11G—C11B—C11A | 115.7 (2) |
C1D1—C1G—C1B | 121.5 (3) | C11G—C11B—H11C | 108.4 |
C1E1—C1D1—C1G | 121.7 (3) | C11A—C11B—H11C | 108.4 |
C1E1—C1D1—H1DA | 119.1 | C11G—C11B—H11D | 108.4 |
C1G—C1D1—H1DA | 119.1 | C11A—C11B—H11D | 108.4 |
C1D1—C1E1—C1Z | 120.3 (3) | H11C—C11B—H11D | 107.4 |
C1D1—C1E1—H1EA | 119.8 | C11D—C11G—C11X | 117.0 (3) |
C1Z—C1E1—H1EA | 119.8 | C11D—C11G—C11B | 120.7 (3) |
O1Z—C1Z—C1E1 | 118.8 (3) | C11X—C11G—C11B | 122.3 (3) |
O1Z—C1Z—C1E2 | 122.4 (3) | C11G—C11D—C11E | 122.6 (3) |
C1E1—C1Z—C1E2 | 118.8 (3) | C11G—C11D—H11E | 118.7 |
C1Z—O1Z—H1ZA | 109.5 | C11E—C11D—H11E | 118.7 |
C1D2—C1E2—C1Z | 120.3 (3) | C11Z—C11E—C11D | 119.4 (3) |
C1D2—C1E2—H1EB | 119.8 | C11Z—C11E—H11F | 120.3 |
C1Z—C1E2—H1EB | 119.8 | C11D—C11E—H11F | 120.3 |
C1E2—C1D2—C1G | 121.7 (3) | O11Z—C11Z—C11E | 122.0 (4) |
C1E2—C1D2—H1DB | 119.2 | O11Z—C11Z—C11Y | 118.8 (4) |
C1G—C1D2—H1DB | 119.2 | C11E—C11Z—C11Y | 119.1 (3) |
O1—C1'—N2 | 122.5 (2) | C11Z—O11Z—H11G | 109.5 |
O1—C1'—C1A | 119.62 (19) | C11X—C11Y—C11Z | 120.9 (3) |
N2—C1'—C1A | 117.9 (2) | C11X—C11Y—H11H | 119.5 |
C1'—N2—C2A | 120.2 (2) | C11Z—C11Y—H11H | 119.6 |
C1'—N2—H2D | 119.9 | C11Y—C11X—C11G | 120.9 (3) |
C2A—N2—H2D | 119.9 | C11Y—C11X—H11I | 119.6 |
N2—C2A—C2' | 108.4 (2) | C11G—C11X—H11I | 119.6 |
N2—C2A—C2B | 111.6 (2) | O11—C11'—N12 | 123.2 (2) |
C2'—C2A—C2B | 110.2 (2) | O11—C11'—C11A | 119.3 (2) |
N2—C2A—H2AA | 108.8 | N12—C11'—C11A | 117.5 (2) |
C2'—C2A—H2AA | 108.8 | C11'—N12—C12A | 119.7 (2) |
C2B—C2A—H2AA | 108.8 | C11'—N12—H12D | 120.1 |
C2A—C2B—H2BA | 109.5 | C12A—N12—H12D | 120.1 |
C2A—C2B—H2BB | 109.5 | N12—C12A—C12B | 113.0 (3) |
H2BA—C2B—H2BB | 109.5 | N12—C12A—C12' | 108.0 (3) |
C2A—C2B—H2BC | 109.5 | C12B—C12A—C12' | 110.7 (3) |
H2BA—C2B—H2BC | 109.5 | N12—C12A—H12E | 108.3 |
H2BB—C2B—H2BC | 109.5 | C12B—C12A—H12E | 108.3 |
O2—C2'—N3 | 122.6 (2) | C12'—C12A—H12E | 108.3 |
O2—C2'—C2A | 120.8 (2) | C12A—C12B—H12F | 109.5 |
N3—C2'—C2A | 116.6 (2) | C12A—C12B—H12G | 109.5 |
C2'—N3—C3A | 120.6 (2) | H12F—C12B—H12G | 109.5 |
C2'—N3—H3D | 119.7 | C12A—C12B—H12H | 109.5 |
C3A—N3—H3D | 119.7 | H12F—C12B—H12H | 109.5 |
N3—C3A—C3' | 111.8 (2) | H12G—C12B—H12H | 109.5 |
N3—C3A—H3AA | 109.3 | O12—C12'—N13 | 122.6 (3) |
C3'—C3A—H3AA | 109.3 | O12—C12'—C12A | 122.4 (3) |
N3—C3A—H3AB | 109.3 | N13—C12'—C12A | 115.0 (3) |
C3'—C3A—H3AB | 109.3 | C12'—N13—C13A | 122.3 (3) |
H3AA—C3A—H3AB | 107.9 | C12'—N13—H13D | 118.9 |
O3—C3'—N4 | 123.8 (2) | C13A—N13—H13D | 118.9 |
O3—C3'—C3A | 120.5 (2) | N13—C13A—C13' | 110.5 (3) |
N4—C3'—C3A | 115.7 (2) | N13—C13A—H13E | 109.6 |
C3'—N4—C4A | 119.6 (2) | C13'—C13A—H13E | 109.6 |
C3'—N4—C4N | 121.8 (2) | N13—C13A—H13F | 109.6 |
C4A—N4—C4N | 118.52 (19) | C13'—C13A—H13F | 109.6 |
N4—C4N—H4NA | 109.5 | H13E—C13A—H13F | 108.1 |
N4—C4N—H4NB | 109.5 | O13—C13'—N14 | 123.8 (2) |
H4NA—C4N—H4NB | 109.5 | O13—C13'—C13A | 120.2 (2) |
N4—C4N—H4NC | 109.5 | N14—C13'—C13A | 116.0 (2) |
H4NA—C4N—H4NC | 109.5 | C13'—N14—C14A | 118.2 (2) |
H4NB—C4N—H4NC | 109.5 | C13'—N14—C14N | 122.6 (2) |
N4—C4A—C4B | 112.4 (2) | C14A—N14—C14N | 118.81 (19) |
N4—C4A—C4' | 109.9 (2) | N14—C14N—H14D | 109.5 |
C4B—C4A—C4' | 111.0 (2) | N14—C14N—H14E | 109.5 |
N4—C4A—H4AA | 107.8 | H14D—C14N—H14E | 109.5 |
C4B—C4A—H4AA | 107.8 | N14—C14N—H14F | 109.5 |
C4'—C4A—H4AA | 107.8 | H14D—C14N—H14F | 109.5 |
C4G—C4B—C4A | 112.0 (2) | H14E—C14N—H14F | 109.5 |
C4G—C4B—H4BA | 109.2 | N14—C14A—C14' | 112.0 (2) |
C4A—C4B—H4BA | 109.2 | N14—C14A—C14B | 112.1 (2) |
C4G—C4B—H4BB | 109.2 | C14'—C14A—C14B | 110.87 (18) |
C4A—C4B—H4BB | 109.2 | N14—C14A—H14G | 107.2 |
H4BA—C4B—H4BB | 107.9 | C14'—C14A—H14G | 107.2 |
C4D1—C4G—C4D2 | 118.6 (3) | C14B—C14A—H14G | 107.2 |
C4D1—C4G—C4B | 121.2 (3) | C14G—C14B—C14A | 111.26 (19) |
C4D2—C4G—C4B | 120.1 (3) | C14G—C14B—H14H | 109.4 |
C4E1—C4D1—C4G | 121.4 (3) | C14A—C14B—H14H | 109.4 |
C4E1—C4D1—H4DA | 119.3 | C14G—C14B—H14I | 109.4 |
C4G—C4D1—H4DA | 119.3 | C14A—C14B—H14I | 109.4 |
C4Z—C4E1—C4D1 | 120.3 (3) | H14H—C14B—H14I | 108.0 |
C4Z—C4E1—H4EA | 119.9 | C14D—C14G—C14X | 117.5 (3) |
C4D1—C4E1—H4EA | 119.9 | C14D—C14G—C14B | 121.6 (3) |
C4E1—C4Z—C4E2 | 119.5 (3) | C14X—C14G—C14B | 120.9 (3) |
C4E1—C4Z—H4ZA | 120.2 | C14G—C14D—C14E | 121.5 (3) |
C4E2—C4Z—H4ZA | 120.2 | C14G—C14D—H14J | 119.3 |
C4Z—C4E2—C4D2 | 120.9 (3) | C14E—C14D—H14J | 119.3 |
C4Z—C4E2—H4EB | 119.6 | C14Z—C14E—C14D | 120.1 (3) |
C4D2—C4E2—H4EB | 119.6 | C14Z—C14E—H14K | 119.9 |
C4G—C4D2—C4E2 | 119.3 (3) | C14D—C14E—H14K | 119.9 |
C4G—C4D2—H4DB | 120.3 | C14Y—C14Z—C14E | 119.2 (3) |
C4E2—C4D2—H4DB | 120.3 | C14Y—C14Z—H14L | 120.4 |
O4—C4'—N5 | 122.2 (2) | C14E—C14Z—H14L | 120.4 |
O4—C4'—C4A | 122.5 (3) | C14Z—C14Y—C14X | 121.0 (3) |
N5—C4'—C4A | 115.3 (2) | C14Z—C14Y—H14M | 119.5 |
C4'—N5—C5A | 122.6 (2) | C14X—C14Y—H14M | 119.5 |
C4'—N5—H5A | 118.7 | C14Y—C14X—C14G | 120.7 (3) |
C5A—N5—H5A | 118.7 | C14Y—C14X—H14N | 119.6 |
N5—C5A—C5' | 110.3 (2) | C14G—C14X—H14N | 119.6 |
N5—C5A—C5B | 110.0 (2) | O14—C14'—N15 | 123.4 (2) |
C5'—C5A—C5B | 111.3 (2) | O14—C14'—C14A | 122.9 (2) |
N5—C5A—H5AA | 108.4 | N15—C14'—C14A | 113.6 (2) |
C5'—C5A—H5AA | 108.4 | C14'—N15—C15A | 123.9 (2) |
C5B—C5A—H5AA | 108.4 | C14'—N15—H15A | 118.0 |
C5G'—C5B—C5A | 121.3 (6) | C15A—N15—H15A | 118.0 |
C5G'—C5B—C5G | 15.3 (7) | N15—C15A—C15' | 108.0 (2) |
C5A—C5B—C5G | 106.2 (3) | N15—C15A—C15B | 110.92 (19) |
C5G'—C5B—H5BA | 103.7 | C15'—C15A—C15B | 113.7 (2) |
C5A—C5B—H5BA | 110.5 | N15—C15A—H15B | 108.0 |
C5G—C5B—H5BA | 110.5 | C15'—C15A—H15B | 108.0 |
C5G'—C5B—H5BB | 101.2 | C15B—C15A—H15B | 108.0 |
C5A—C5B—H5BB | 110.5 | C15G—C15B—C15A | 114.6 (2) |
C5G—C5B—H5BB | 110.5 | C15G—C15B—H15C | 108.6 |
H5BA—C5B—H5BB | 108.7 | C15A—C15B—H15C | 108.6 |
C5B—C5G—S5 | 112.0 (5) | C15G—C15B—H15D | 108.6 |
C5B—C5G—H5GA | 109.2 | C15A—C15B—H15D | 108.6 |
S5—C5G—H5GA | 109.2 | H15C—C15B—H15D | 107.6 |
C5B—C5G—H5GB | 109.2 | C15B—C15G—S15 | 114.28 (19) |
S5—C5G—H5GB | 109.2 | C15B—C15G—H15E | 108.7 |
H5GA—C5G—H5GB | 107.9 | S15—C15G—H15E | 108.7 |
C5G—S5—C5D | 98.1 (4) | C15B—C15G—H15F | 108.7 |
S5—C5D—H5DA | 109.5 | S15—C15G—H15F | 108.7 |
S5—C5D—H5DB | 109.5 | H15E—C15G—H15F | 107.6 |
H5DA—C5D—H5DB | 109.5 | C15D—S15—C15G | 103.3 (2) |
S5—C5D—H5DC | 109.5 | S15—C15D—H15G | 109.5 |
H5DA—C5D—H5DC | 109.5 | S15—C15D—H15H | 109.5 |
H5DB—C5D—H5DC | 109.5 | H15G—C15D—H15H | 109.5 |
C5B—C5G'—S5' | 121.5 (8) | S15—C15D—H15I | 109.5 |
C5B—C5G'—H5GC | 106.9 | H15G—C15D—H15I | 109.5 |
S5'—C5G'—H5GC | 107.0 | H15H—C15D—H15I | 109.5 |
C5B—C5G'—H5GD | 107.0 | O15—C15'—O15' | 123.4 (2) |
S5'—C5G'—H5GD | 107.0 | O15—C15'—C15A | 125.4 (2) |
H5GC—C5G'—H5GD | 106.7 | O15'—C15'—C15A | 111.1 (2) |
C5G'—S5'—C5D' | 92.7 (7) | C15'—O15'—C16 | 116.0 (2) |
S5'—C5D'—H5DD | 109.5 | O15'—C16—H16A | 109.5 |
S5'—C5D'—H5DE | 109.5 | O15'—C16—H16B | 109.5 |
H5DD—C5D'—H5DE | 109.5 | H16A—C16—H16B | 109.5 |
S5'—C5D'—H5DF | 109.5 | O15'—C16—H16C | 109.5 |
H5DD—C5D'—H5DF | 109.5 | H16A—C16—H16C | 109.5 |
H5DE—C5D'—H5DF | 109.5 | H16B—C16—H16C | 109.5 |
O5—C5'—O5' | 123.9 (2) | H1SA—O1S—H1SB | 110 (3) |
O5—C5'—C5A | 124.0 (2) | H2SA—O2S—H2SB | 108 (3) |
O5'—C5'—C5A | 112.1 (2) |
Symmetry code: (i) −x, y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O15 | 0.86 | 2.29 | 3.036 (3) | 145 |
O1Z—H1ZA···O1S | 0.82 | 1.89 | 2.708 (3) | 179 |
N2—H2D···O2ii | 0.86 | 2.11 | 2.960 (3) | 169 |
N3—H3D···O13 | 0.86 | 2.26 | 3.029 (3) | 149 |
N5—H5A···O11 | 0.86 | 2.07 | 2.865 (3) | 153 |
N11—H11A···O5 | 0.86 | 2.26 | 3.017 (3) | 146 |
O11Z—H11G···O2Siii | 0.82 | 1.93 | 2.745 (5) | 175 |
N12—H12D···O12i | 0.86 | 2.10 | 2.956 (4) | 171 |
N13—H13D···O3 | 0.86 | 2.05 | 2.902 (3) | 169 |
N15—H15A···O1 | 0.86 | 2.00 | 2.828 (3) | 161 |
O1S—H1SA···O2iv | 0.85 (4) | 2.02 (4) | 2.842 (3) | 164 (3) |
O1S—H1SB···O0iii | 0.86 (3) | 2.00 (3) | 2.827 (3) | 160 (4) |
O2S—H2SA···O15" | 0.89 (2) | 1.93 (2) | 2.821 (3) | 175 (4) |
O2S—H2SB···O3Si | 0.87 (2) | 1.76 (3) | 2.521 (14) | 144 (4) |
O2S—H2SB···O3S | 0.87 (2) | 2.01 (3) | 2.768 (14) | 144 (3) |
Symmetry codes: (i) −x, y, −z; (ii) −x, y, −z+1; (iii) x, y+1, z; (iv) −x, y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C35H49N5O9S·H2O·0.125O |
Mr | 735.87 |
Crystal system, space group | Monoclinic, C2 |
Temperature (K) | 153 |
a, b, c (Å) | 38.354 (1), 11.000 (1), 22.689 (1) |
β (°) | 123.15 (1) |
V (Å3) | 8014.4 (8) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 1.21 |
Crystal size (mm) | 0.52 × 0.50 × 0.46 |
Data collection | |
Diffractometer | Bruker SMART 6000 CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.559, 0.573 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17149, 10567, 8802 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.588 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.112, 1.01 |
No. of reflections | 10567 |
No. of parameters | 966 |
No. of restraints | 11 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.23 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.00 (2) |
Computer programs: SMART (Bruker, 1999), SMART, SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXS97.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O15 | 0.86 | 2.29 | 3.036 (3) | 145.1 |
O1Z—H1ZA···O1S | 0.82 | 1.89 | 2.708 (3) | 179.3 |
N2—H2D···O2i | 0.86 | 2.11 | 2.960 (3) | 169.0 |
N3—H3D···O13 | 0.86 | 2.26 | 3.029 (3) | 148.8 |
N5—H5A···O11 | 0.86 | 2.07 | 2.865 (3) | 152.5 |
N11—H11A···O5 | 0.86 | 2.26 | 3.017 (3) | 146.4 |
O11Z—H11G···O2Sii | 0.82 | 1.93 | 2.745 (5) | 175.2 |
N12—H12D···O12iii | 0.86 | 2.10 | 2.956 (4) | 170.5 |
N13—H13D···O3 | 0.86 | 2.05 | 2.902 (3) | 168.9 |
N15—H15A···O1 | 0.86 | 2.00 | 2.828 (3) | 160.5 |
O1S—H1SA···O2iv | 0.85 (4) | 2.02 (4) | 2.842 (3) | 164 (3) |
O1S—H1SB···O0ii | 0.86 (3) | 2.00 (3) | 2.827 (3) | 160 (4) |
O2S—H2SA···O15" | 0.89 (2) | 1.93 (2) | 2.821 (3) | 175 (4) |
O2S—H2SB···O3Siii | 0.87 (2) | 1.76 (3) | 2.521 (14) | 144 (4) |
O2S—H2SB···O3S | 0.87 (2) | 2.01 (3) | 2.768 (14) | 144 (3) |
Symmetry codes: (i) −x, y, −z+1; (ii) x, y+1, z; (iii) −x, y, −z; (iv) −x, y+1, −z+1. |
Theoretically, linear peptides can have many different backbone conformations. Early X-ray studies (1983–1987) on enkephalin and its analogues showed only two different backbone conformations: extended and single β-bend. No other conformations were observed until a double β-bend was reported in 1989 (for a review, see Deschamps et al., 1996). Despite the small number of conformations observed in the solid state, most enkephalin analogues can adopt many conformations in solution. To constrain the peptide conformation a number of modifications have been investigated, including the substitution, deletion or addition of natural or artificial amino acids and the formation of highly constrained peptide ring systems. In this study, we report on the X-ray diffraction analysis of the pentapeptide, Boc-Tyr-D-Ala-Gly-NMe-Phe-Met-OMe, a protected intermediate in the solution phase synthesis of metkephamid (LY127,623). Metkephamide (Tyr-D-Ala-Gly-NMe-Phe-Met-NH2) is an analog of methionine-enkephalin that retains high affinity for the delta receptor, and has systemic analgesic activity (Frederickson et al., 1981).
The title compound, (I), crystallizes with two peptide molecules and three water molecules in the asymmetric unit (Fig. 1). Additional disordered water molecules are probably present in the crystal, as evidenced by the diffuse residual electron density and voids large enough to accommodate a water molecule were detected by PLATON (Spek, 2001). The two independent peptides molecules have an extended conformation, although even the main-chain atoms cannot be fully superimposed (Fig 2). The extended conformation observed in this study is similar to that of other Met-enkephalins (Doi et al., 1984; Griffin et al., 1986; Doi et al., 1987).
The peptide molecules form an extensive hydrogen bonded network (Table 1). Pairs of adjacent peptide molecules are linked across the chains by six hydrogen bonds (Fig. 3). These pairs are then linked to adjacent pairs by two hydrogen bonds forming extended ribbons. This pattern of cross-chain hydrogen bonds is typical of enkaphalins with an extended conformation (Karle et al., 1983; Griffin et al., 1986; Doi et al., 1987). Two of the solvent (i.e. water) molecules form hydrogen bonds between adjacent ribbons, the third water molecule (O3S) interacts only with other solvent molecules.
In this study, the X-ray diffraction data was collected using a Bruker SMART 6000 detector and a copper rotating anode. Prior to this, we collected X-ray diffraction data at the Cornell High Energy Synchrotron Source (CHESS). The structure determined from the synchrotron data is identical to that reported here. However, the synchrotron determined structure suffered from an incomplete dataset (due to the experimental set up) and unusually large sigmas for the measured intensities. Because of these problems the structure-solution for the synchrotron data was more difficult and the structure did not refine as well.