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Ceratospong­amide (CS) is a potent inhibitor of secreted phospho­lipase A2, and cis,cis and trans,trans isomers, related with respect to the two proline amide bonds, are known. Crystals of cis,cis-CS were grown from N,N-di­methyl­acet­amide solution, giving the title compound, the cyclic ester of isoleucyl­oxazolinyl­phenyl­alanyl­prolyl­thia­zolyl­phenyl­alanyl­pro­line [cyclo(-Ile-Oxz-Phe-Pro-Thz-Phe-Pro-)] N,N-di­methyl­acet­amide hemisolvate, C41H49N7O6S·0.5C4H9NO. The structure is the third example of cis,cis-CS to be investigated and comprises twinned crystals, in which the a and b axes are interchanged. The ratio of co-existing twin crystals is approximately 50%. The peptide has a `saddle-like' structure and is very similar to previously reported structures of cis,cis-CS, which implies that the structure of cis,cis-CS is very stable in spite of differences in crystallization conditions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010300369X/ob1101sup1.cif
Contains datablocks ccs1, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010300369X/ob1101Isup2.hkl
Contains datablock I

CCDC reference: 214405

Comment top

Ceratospongamide (CS) is a cyclic heptapeptide containing oxazoline (Oxz) and thiazole (Thz) that has two isomers, namely cis,cis –CS and trans,trans-CS, that show different bioactivities (Tan et al., 2000). The isomerization is caused by the cis and trans rotamers of the proline residues (see the closed bonds in Fig. 2), and the peptide conformation is directly related to the activity. Recent work has suggested that the conversion from the cis,cis to the trans,trans isomer is accompanied by the chiral reverse of Ile (Yokogawa et al., 2002) or Oxz (Kutsumura et al., 2002). Therefore, CS is of interest in the investigation of relationships between structure and activity (Yokokawa et al., 2001; Deng & Taunton, 2002). Two crystal forms of cis,cis-CS were known previously (Doi, Yumiba & Asano, 2002; Doi & Asano, 2002). Crystals of the title compound, (I), were grown from N,N-dimethylacetoamide (DMA) in the presence of twinning, and the structure of (I) is reported here.

In (I), two peptide molecules are located in the asymmetric unit with a solvent DMA molecule (Fig. 1). A cis rotamer is observed for the Pro4 and Pro7 residues of both molecules (Table 1). The structures of cis,cis-CS are very similar to each other, and no significant difference is observed in the conformations of the peptide backbones (Table 1). The shape of the peptide ring is 'saddle'-like, and the cis-Pro residues are located at turns of the ring (Fig.2). The Ile1/ Oxz2/Phe3 moiety faces that of Thz5/Phe6, but no intramolecular hydrogen bond is formed. The amide plane of Oxz2—Phe3 is stacked to the Thz ring. These features are similar to those of two previously known structures of cis,cis-CS (Doi & Asano, 2002; Doi, Yumiba & Asano, 2002); a superposition of the four structures is shown in Fig.3. Molecular fitting for Cα atoms resulted in r.m.s. deviations of 0.019–0.041 Å. The peptide backbones are very similar to each other, and relatively large shifts are only observed for the side chains of Ile1 and Phe3. It is surprising that similar structures are found in crystals grown under three different conditions. This result suggests that the structures of cis,cis-CS are very stable.

Experimental top

CS was synthesized as previously described (Yokokawa et al., 2001). The peptide was dissolved in DMA (7–10 mg per 0.10–0.15 ml of DMA), and crystals of (I) were grown for 2–3 weeks. The single-crystal selected for investigation was briefly passed through glycerol and was mounted on a nylon loop under a nitrogen stream at 90 K.

Refinement top

Reflections were measured for the full sphere. The camera distance of 60 mm was presumed to ??cause a problem??, with the peak separation along the longest c axis being 53.536 (3) Å when Mo Kα radiation was used. However, a capillary collimator (causing total external reflection) gave a clear peak separation even for relatively strong reflections (Fig.4), and the peak intensities were properly integrated. The data were processed with XPREP (Bruker, 2001), and the merging processes resulted in Rint values of 0.039 and 0.041 for the orthorhombic and tetragonal systems, respectively. The mean value of |E2-1| was 0.548, where the theoretical values of 0.938 and 0.736 were expected for centric and acentric space groups, respectively (Iwasaki & Ito, 1977).

The crystal system could not be determined at the early stage of the analysis, but the solution was finally obtained from the space group P212121 using the dual-spacing recycling method (Sheldrick & Gould, 1996). ??The orthorhombic lattice with a and b axes equal in length was emulating tetragonal.?? The test for twinning using XPREP (Bruker, 2001) showed a sign of 'partial merohedral twinning'. Moreover, straightforward refinements did not converge for the solved structure. Therefore, twinning with the a and b axes swapped was accounted for in the refinement using SHELXL (Sheldrick, 1997). The ratio of twinning was 0.492 (1). H atoms were ?placed on the basis of their ideal positions and refined as riding atoms??.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINTPLUS (Bruker, 1998); program(s) used to solve structure: SHELXD (Seldrick & Gould, 1996); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PARST (Nardelli, 1983).

Figures top
[Figure 1] Fig. 1. The structure of cis,cis-CS. The component of the asymmetric unit of (I) was drawn with displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. The peptide backbone. Side chains have been omitted for clarity. The closed bonds around the Pro residues indicate the cis-amide bonds.
[Figure 3] Fig. 3. A superposition of the four molecules of cis,cis-CS in the three crystal forms.
[Figure 4] Fig. 4. A CCD image and peak profile along the longest c axis. (a) Layered spots showing the longest c axis. The peak profiles (b) and (c) were produced along the layers indicated in (a) by arrows b and c, respectively.
cis,cis-Ceratospongamide, N,N-dimethylacetamide hemisolvate cyclo(–Ile-Oxz-Phe-Pro-Thz-Phe-Pro-) top
Crystal data top
C41H49N7O6S·0.5C4H9NODx = 1.267 Mg m3
Mr = 811.51Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 8337 reflections
a = 12.6034 (7) Åθ = 2.3–27.7°
b = 12.6075 (7) ŵ = 0.13 mm1
c = 53.536 (3) ÅT = 90 K
V = 8506.7 (8) Å3Plate, colorless
Z = 80.45 × 0.30 × 0.10 mm
F(000) = 3456
Data collection top
Bruker AXS SMART APEX area detector
diffractometer
20493 independent reflections
Radiation source: MacScience M18XCE rotating anode20401 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
Detector resolution: 8.366 pixels mm-1θmax = 28.3°, θmin = 1.1°
ω scanh = 1616
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1616
Tmin = 0.883, Tmax = 0.987l = 7170
102830 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.0783P)2 + 1.9396P]
where P = (Fo2 + 2Fc2)/3
S = 1.16(Δ/σ)max = 0.012
20493 reflectionsΔρmax = 0.86 e Å3
1046 parametersΔρmin = 0.27 e Å3
0 restraintsAbsolute structure: (Flack, 1983), 8904 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.09 (6)
Crystal data top
C41H49N7O6S·0.5C4H9NOV = 8506.7 (8) Å3
Mr = 811.51Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 12.6034 (7) ŵ = 0.13 mm1
b = 12.6075 (7) ÅT = 90 K
c = 53.536 (3) Å0.45 × 0.30 × 0.10 mm
Data collection top
Bruker AXS SMART APEX area detector
diffractometer
20493 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
20401 reflections with I > 2σ(I)
Tmin = 0.883, Tmax = 0.987Rint = 0.038
102830 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.127Δρmax = 0.86 e Å3
S = 1.16Δρmin = 0.27 e Å3
20493 reflectionsAbsolute structure: (Flack, 1983), 8904 Friedel pairs
1046 parametersAbsolute structure parameter: 0.09 (6)
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N_111.0954 (2)0.9757 (2)0.07393 (5)0.0237 (5)
H1_111.03860.96940.08340.028*
CA_111.1023 (2)1.0612 (2)0.05547 (5)0.0203 (5)
H2_111.17891.07220.05130.024*
CB_111.0566 (2)1.1684 (2)0.06495 (5)0.0213 (5)
H3_111.06121.22030.05090.026*
CG2_111.1257 (3)1.2099 (3)0.08609 (6)0.0312 (7)
H4_111.19951.21420.08040.047*
H5_111.10111.28050.09110.047*
H6_111.12101.16160.10040.047*
CG1_110.9397 (3)1.1598 (3)0.07247 (7)0.0275 (6)
H7_110.93471.11730.08800.033*
H8_110.90101.12100.05920.033*
CD_110.8857 (3)1.2654 (3)0.07672 (8)0.0391 (8)
H9_110.81161.25360.08150.059*
H10_110.92221.30380.09010.059*
H11_110.88841.30740.06130.059*
C3_121.0449 (2)1.0285 (2)0.03183 (5)0.0196 (5)
N_120.9768 (2)0.9570 (2)0.02982 (5)0.0227 (5)
CA_120.9383 (2)0.9629 (2)0.00380 (5)0.0208 (5)
H1_120.95530.89500.00500.025*
CB_121.0011 (2)1.0548 (2)0.00859 (5)0.0203 (5)
H2_120.95111.11250.01370.024*
OG1_121.06879 (18)1.09188 (19)0.01193 (4)0.0245 (5)
CG2_121.0707 (3)1.0249 (3)0.03038 (6)0.0261 (6)
H3_121.10691.08830.03670.039*
H4_121.12350.97280.02490.039*
H5_121.02700.99420.04370.039*
C_120.8192 (2)0.9837 (2)0.00210 (6)0.0220 (6)
O_120.7757 (2)0.9947 (2)0.01791 (4)0.0326 (5)
N_130.7684 (2)0.9918 (2)0.02427 (5)0.0228 (5)
H1_130.80440.98070.03810.027*
CA_130.6560 (2)1.0184 (3)0.02602 (5)0.0221 (6)
H2_130.61460.97800.01320.026*
CB_130.6395 (2)1.1383 (2)0.02243 (6)0.0225 (5)
H3_130.66581.15950.00570.027*
H4_130.68081.17750.03520.027*
CG_130.5221 (2)1.1672 (2)0.02479 (6)0.0243 (6)
CD1_130.4513 (3)1.1447 (3)0.00601 (7)0.0318 (7)
H5_130.47511.11010.00870.038*
CE1_130.3438 (3)1.1729 (3)0.00848 (7)0.0355 (8)
H6_130.29501.15570.00440.043*
CZ_130.3092 (3)1.2247 (3)0.02927 (7)0.0346 (8)
H7_130.23651.24380.03080.042*
CE2_130.3808 (3)1.2499 (3)0.04855 (7)0.0348 (7)
H8_130.35741.28790.06290.042*
CD2_130.4862 (3)1.2186 (2)0.04641 (6)0.0248 (6)
H9_130.53421.23220.05970.030*
C_130.6208 (2)0.9862 (3)0.05250 (6)0.0235 (6)
O_130.6546 (2)1.0365 (2)0.07044 (4)0.0331 (5)
N_140.5565 (2)0.9029 (2)0.05508 (5)0.0204 (5)
CA_140.5234 (2)0.8289 (2)0.03504 (6)0.0223 (6)
H1_140.48510.86750.02150.027*
CB_140.4480 (2)0.7541 (3)0.04915 (6)0.0262 (6)
H2_140.37460.78200.04910.031*
H3_140.44820.68240.04160.031*
CG_140.4930 (3)0.7513 (3)0.07594 (6)0.0312 (7)
H4_140.55390.70190.07720.037*
H5_140.43800.72980.08810.037*
CD_140.5280 (3)0.8657 (3)0.08026 (6)0.0295 (7)
H6_140.58980.86900.09170.035*
H7_140.46950.90860.08740.035*
C3_150.6203 (2)0.7721 (2)0.02484 (5)0.0193 (5)
N_150.70147 (19)0.7452 (2)0.03833 (5)0.0210 (5)
CA_150.7759 (2)0.6943 (3)0.02420 (6)0.0222 (6)
CB_150.7523 (2)0.6803 (2)0.00046 (5)0.0210 (5)
H1_150.79550.64470.01230.025*
SG_150.63120 (5)0.73790 (6)0.006472 (12)0.01943 (13)
C_150.8797 (2)0.6640 (2)0.03552 (5)0.0201 (5)
O_150.95088 (18)0.6215 (2)0.02345 (4)0.0288 (5)
N_160.8880 (2)0.6919 (2)0.05976 (5)0.0246 (5)
H1_160.83180.71760.06740.030*
CA_160.9864 (2)0.6809 (2)0.07371 (5)0.0223 (5)
H2_161.04710.70820.06350.027*
C_160.9728 (2)0.7488 (3)0.09714 (5)0.0254 (6)
O_160.88736 (18)0.7489 (2)0.10802 (4)0.0344 (5)
CB_161.0071 (3)0.5632 (3)0.08124 (6)0.0287 (7)
H3_160.99640.51720.06650.034*
H4_160.95510.54180.09410.034*
CG_161.1180 (2)0.5463 (2)0.09125 (6)0.0220 (6)
CD1_161.1374 (3)0.5466 (3)0.11633 (6)0.0286 (7)
H5_161.08040.55610.12770.034*
CE1_161.2412 (4)0.5329 (3)0.12540 (7)0.0358 (8)
H6_161.25470.53230.14290.043*
CZ_161.3242 (3)0.5201 (3)0.10837 (10)0.0434 (10)
H7_161.39510.51330.11420.052*
CE2_161.3037 (3)0.5174 (3)0.08353 (9)0.0410 (10)
H8_161.36010.50640.07200.049*
CD2_161.2012 (3)0.5306 (3)0.07473 (7)0.0315 (7)
H9_161.18780.52880.05730.038*
N_171.05478 (19)0.8074 (2)0.10558 (4)0.0193 (5)
CA_171.1625 (2)0.8155 (2)0.09506 (5)0.0177 (5)
H1_171.18330.74680.08710.021*
CB_171.2300 (2)0.8356 (2)0.11824 (5)0.0236 (6)
H2_171.24810.76820.12670.028*
H3_171.29630.87330.11390.028*
CG_171.1582 (3)0.9050 (3)0.13484 (6)0.0257 (6)
H4_171.15970.98000.12940.031*
H5_171.17960.90070.15260.031*
CD_171.0489 (3)0.8562 (3)0.13078 (6)0.0270 (6)
H6_170.99290.91130.13140.032*
H7_171.03350.80190.14370.032*
C_171.1757 (2)0.9071 (2)0.07638 (5)0.0194 (5)
O_171.2583 (2)0.9164 (2)0.06496 (6)0.0429 (7)
N_210.2861 (2)0.2251 (2)0.17215 (4)0.0216 (5)
H1_210.29910.27360.16070.026*
CA_210.1910 (3)0.2355 (4)0.18764 (6)0.0330 (8)
H2_210.15670.16490.19040.040*
CB_210.1098 (3)0.3170 (4)0.17379 (7)0.0376 (8)
H3_210.14850.38480.17040.045*
CG2_210.0137 (3)0.3420 (4)0.19044 (8)0.0472 (10)
H4_210.03820.37300.20620.071*
H5_210.03290.39240.18190.071*
H6_210.02550.27640.19390.071*
CG1_210.0761 (3)0.2678 (3)0.14821 (7)0.0357 (7)
H7_210.14010.25830.13770.043*
H8_210.02850.31810.13950.043*
CD_210.0212 (4)0.1641 (3)0.15071 (8)0.0434 (9)
H9_210.00220.13750.13410.065*
H10_210.06850.11330.15900.065*
H11_210.04330.17320.16070.065*
C3_220.2200 (2)0.2868 (3)0.21226 (5)0.0226 (6)
N_220.2919 (2)0.3552 (2)0.21507 (5)0.0246 (5)
CA_220.2848 (2)0.3903 (2)0.24106 (5)0.0184 (5)
H1_220.35160.37060.25000.022*
CB_220.1899 (2)0.3273 (2)0.25270 (5)0.0209 (6)
H2_220.13050.37710.25670.025*
OG1_220.15892 (17)0.25733 (19)0.23197 (4)0.0235 (4)
CG2_220.2156 (3)0.2605 (3)0.27529 (5)0.0262 (6)
H3_220.15110.22480.28110.039*
H4_220.26890.20720.27080.039*
H5_220.24340.30590.28860.039*
C_220.2660 (2)0.5101 (3)0.24386 (5)0.0224 (6)
O_220.2623 (2)0.5508 (2)0.26429 (4)0.0366 (6)
N_230.2512 (2)0.5611 (2)0.22214 (5)0.0277 (6)
H1_230.25490.52480.20810.033*
CA_230.2295 (2)0.6732 (3)0.22093 (5)0.0211 (5)
H2_230.26940.71100.23440.025*
CB_230.1091 (2)0.6951 (3)0.22366 (6)0.0248 (6)
H3_230.08370.66390.23950.030*
H4_230.07080.65970.20980.030*
CG_230.0831 (2)0.8120 (3)0.22338 (6)0.0261 (6)
CD1_230.0287 (3)0.8568 (3)0.20365 (6)0.0302 (7)
H5_230.00880.81410.18980.036*
CE1_230.0030 (3)0.9639 (3)0.20392 (7)0.0393 (9)
H6_230.03640.99360.19050.047*
CZ_230.0339 (3)1.0262 (3)0.22321 (8)0.0370 (8)
H7_230.01721.09970.22310.044*
CE2_230.0897 (3)0.9837 (3)0.24310 (8)0.0420 (9)
H8_230.11041.02750.25670.050*
CD2_230.1152 (3)0.8766 (3)0.24302 (7)0.0333 (7)
H9_230.15470.84730.25650.040*
C_230.2689 (2)0.7105 (2)0.19511 (5)0.0207 (5)
O_230.2188 (2)0.6862 (2)0.17656 (4)0.0338 (5)
N_240.36046 (19)0.7647 (2)0.19413 (4)0.0198 (4)
CA_240.4296 (2)0.7944 (2)0.21538 (5)0.0185 (5)
H1_240.38780.83120.22870.022*
CB_240.5078 (2)0.8724 (2)0.20263 (6)0.0226 (6)
H2_240.57660.87450.21160.027*
H3_240.47790.94500.20190.027*
CG_240.5207 (2)0.8253 (3)0.17635 (5)0.0233 (6)
H4_240.57130.76520.17640.028*
H5_240.54580.87960.16440.028*
CD_240.4090 (2)0.7881 (2)0.16985 (5)0.0204 (5)
H6_240.41130.72380.15920.025*
H7_240.36920.84430.16100.025*
C3_250.4847 (2)0.6971 (2)0.22575 (5)0.0184 (5)
N_250.5111 (2)0.61612 (19)0.21243 (4)0.0192 (5)
CA_250.5615 (2)0.5411 (2)0.22698 (5)0.0203 (5)
CB_250.5773 (2)0.5669 (2)0.25135 (5)0.0175 (5)
H1_250.61430.52490.26320.021*
SG_250.51953 (6)0.68767 (6)0.257144 (11)0.01896 (13)
C_250.5937 (2)0.4365 (2)0.21589 (5)0.0204 (5)
O_250.63395 (19)0.36627 (18)0.22882 (4)0.0245 (4)
N_260.5708 (2)0.42640 (18)0.19163 (4)0.0193 (5)
H1_260.54770.48190.18330.023*
CA_260.5834 (2)0.3254 (2)0.17867 (5)0.0185 (5)
H2_260.55370.26610.18890.022*
CB_260.7042 (2)0.3062 (3)0.17320 (6)0.0249 (6)
H3_260.74480.31330.18890.030*
H4_260.73000.36120.16150.030*
CG_260.7247 (2)0.1978 (3)0.16210 (5)0.0214 (6)
CD1_260.7339 (2)0.1088 (3)0.17757 (6)0.0267 (6)
H5_260.72870.11670.19520.032*
CE1_260.7508 (3)0.0085 (3)0.16719 (8)0.0364 (8)
H6_260.75840.05160.17770.044*
CZ_260.7565 (3)0.0031 (4)0.14139 (8)0.0393 (9)
H7_260.76750.07130.13430.047*
CE2_260.7461 (3)0.0844 (3)0.12604 (6)0.0334 (7)
H8_260.74990.07610.10840.040*
CD2_260.7300 (2)0.1838 (3)0.13624 (5)0.0263 (6)
H9_260.72250.24340.12550.032*
C_260.5254 (2)0.3340 (2)0.15400 (5)0.0192 (5)
O_260.5304 (2)0.41646 (18)0.14181 (4)0.0273 (5)
N_270.47048 (19)0.24794 (19)0.14544 (4)0.0177 (4)
CA_270.4539 (2)0.1465 (2)0.15803 (5)0.0161 (5)
H1_270.51790.12780.16820.019*
CB_270.4428 (3)0.0692 (2)0.13593 (6)0.0246 (6)
H2_270.40090.00600.14070.030*
H3_270.51320.04610.12980.030*
CG_270.3844 (3)0.1357 (3)0.11614 (5)0.0241 (6)
H4_270.39690.10720.09920.029*
H5_270.30710.13720.11940.029*
CD_270.4335 (3)0.2468 (3)0.11907 (5)0.0243 (6)
H6_270.38000.30290.11610.029*
H7_270.49350.25690.10740.029*
C_270.3533 (2)0.1448 (3)0.17474 (5)0.0233 (6)
O_270.3397 (2)0.0706 (3)0.18887 (5)0.0444 (7)
O1_310.8734 (5)0.4650 (4)0.13343 (11)0.115 (3)
C1_310.8190 (5)0.5436 (6)0.14094 (13)0.0780 (19)
C2_310.8236 (8)0.6133 (6)0.16272 (11)0.092 (2)
H1_310.76600.66540.16180.138*
H2_310.81580.57100.17800.138*
H3_310.89200.65030.16300.138*
N1_310.7347 (4)0.5627 (5)0.12776 (12)0.087 (2)
C3_310.7181 (4)0.4969 (4)0.10277 (11)0.0585 (13)
H4_310.65220.51950.09470.088*
H5_310.77800.50950.09150.088*
H6_310.71380.42120.10670.088*
C4_310.6558 (4)0.6504 (5)0.12969 (12)0.0631 (14)
H7_310.60170.64180.11670.095*
H8_310.62200.64840.14620.095*
H9_310.69180.71860.12750.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N_110.0177 (11)0.0296 (14)0.0238 (12)0.0017 (10)0.0001 (9)0.0130 (10)
CA_110.0143 (12)0.0266 (15)0.0200 (12)0.0036 (10)0.0020 (10)0.0054 (11)
CB_110.0235 (13)0.0204 (14)0.0200 (12)0.0033 (11)0.0049 (10)0.0000 (10)
CG2_110.0338 (16)0.0401 (18)0.0198 (13)0.0094 (14)0.0040 (12)0.0026 (12)
CG1_110.0227 (14)0.0197 (14)0.0399 (17)0.0076 (11)0.0020 (13)0.0003 (12)
CD_110.042 (2)0.0285 (18)0.0467 (19)0.0184 (15)0.0022 (16)0.0036 (15)
C3_120.0175 (13)0.0206 (13)0.0207 (12)0.0084 (10)0.0010 (10)0.0056 (10)
N_120.0212 (11)0.0206 (12)0.0264 (11)0.0085 (10)0.0048 (10)0.0048 (9)
CA_120.0203 (13)0.0208 (13)0.0212 (13)0.0007 (10)0.0001 (11)0.0013 (11)
CB_120.0176 (13)0.0189 (12)0.0245 (13)0.0024 (10)0.0033 (10)0.0009 (10)
OG1_120.0287 (11)0.0298 (11)0.0150 (9)0.0052 (9)0.0046 (8)0.0055 (8)
CG2_120.0307 (16)0.0260 (15)0.0217 (13)0.0018 (12)0.0073 (12)0.0012 (11)
C_120.0209 (13)0.0193 (13)0.0257 (13)0.0024 (10)0.0042 (11)0.0036 (11)
O_120.0291 (12)0.0439 (14)0.0247 (11)0.0049 (11)0.0012 (9)0.0009 (10)
N_130.0222 (12)0.0230 (12)0.0232 (12)0.0030 (10)0.0036 (10)0.0008 (10)
CA_130.0182 (13)0.0281 (15)0.0198 (12)0.0030 (11)0.0043 (10)0.0004 (11)
CB_130.0171 (13)0.0195 (13)0.0310 (14)0.0006 (11)0.0004 (11)0.0001 (11)
CG_130.0212 (13)0.0176 (13)0.0340 (14)0.0044 (11)0.0035 (12)0.0096 (11)
CD1_130.0299 (17)0.0288 (16)0.0367 (17)0.0014 (13)0.0009 (14)0.0069 (14)
CE1_130.0278 (16)0.0309 (17)0.048 (2)0.0015 (13)0.0078 (15)0.0085 (15)
CZ_130.0223 (15)0.0355 (18)0.0462 (19)0.0026 (13)0.0048 (13)0.0218 (15)
CE2_130.0379 (18)0.0326 (17)0.0341 (16)0.0020 (15)0.0132 (14)0.0129 (14)
CD2_130.0289 (15)0.0184 (13)0.0270 (13)0.0036 (11)0.0047 (12)0.0112 (11)
C_130.0211 (13)0.0251 (14)0.0243 (13)0.0028 (11)0.0003 (11)0.0013 (11)
O_130.0407 (14)0.0333 (13)0.0253 (11)0.0151 (11)0.0089 (10)0.0021 (9)
N_140.0206 (11)0.0198 (12)0.0210 (11)0.0010 (9)0.0026 (9)0.0051 (9)
CA_140.0137 (12)0.0243 (14)0.0289 (13)0.0017 (11)0.0025 (11)0.0060 (11)
CB_140.0154 (12)0.0272 (15)0.0361 (15)0.0054 (11)0.0100 (11)0.0058 (13)
CG_140.0308 (16)0.0302 (16)0.0325 (15)0.0076 (14)0.0065 (13)0.0007 (13)
CD_140.0277 (16)0.0330 (17)0.0279 (15)0.0052 (13)0.0008 (12)0.0009 (12)
C3_150.0173 (12)0.0184 (13)0.0223 (12)0.0045 (10)0.0037 (10)0.0042 (10)
N_150.0177 (11)0.0216 (12)0.0238 (11)0.0060 (10)0.0030 (9)0.0021 (10)
CA_150.0099 (11)0.0276 (15)0.0292 (14)0.0050 (11)0.0067 (10)0.0023 (12)
CB_150.0140 (12)0.0212 (13)0.0279 (13)0.0022 (10)0.0017 (10)0.0018 (11)
SG_150.0137 (3)0.0237 (3)0.0209 (3)0.0003 (3)0.0013 (2)0.0006 (3)
C_150.0128 (12)0.0194 (13)0.0282 (13)0.0035 (10)0.0074 (10)0.0053 (10)
O_150.0196 (10)0.0353 (12)0.0314 (11)0.0001 (9)0.0012 (9)0.0008 (10)
N_160.0163 (11)0.0333 (14)0.0242 (11)0.0020 (10)0.0019 (9)0.0044 (11)
CA_160.0160 (12)0.0261 (14)0.0247 (12)0.0048 (11)0.0003 (10)0.0046 (11)
C_160.0239 (14)0.0281 (15)0.0241 (13)0.0011 (12)0.0020 (11)0.0096 (12)
O_160.0204 (11)0.0547 (16)0.0282 (11)0.0095 (11)0.0045 (9)0.0031 (11)
CB_160.0293 (16)0.0237 (14)0.0331 (15)0.0106 (12)0.0067 (13)0.0083 (12)
CG_160.0231 (14)0.0142 (12)0.0287 (14)0.0012 (10)0.0018 (11)0.0037 (11)
CD1_160.0335 (17)0.0258 (15)0.0264 (14)0.0047 (13)0.0085 (13)0.0008 (12)
CE1_160.052 (2)0.0284 (17)0.0274 (16)0.0002 (16)0.0121 (15)0.0044 (13)
CZ_160.0203 (16)0.0208 (16)0.089 (3)0.0007 (12)0.0039 (18)0.0088 (18)
CE2_160.0294 (17)0.0210 (16)0.073 (3)0.0056 (13)0.0244 (18)0.0013 (17)
CD2_160.0382 (18)0.0239 (15)0.0323 (16)0.0016 (13)0.0111 (14)0.0016 (13)
N_170.0166 (10)0.0229 (12)0.0183 (10)0.0002 (9)0.0030 (8)0.0049 (9)
CA_170.0136 (11)0.0189 (12)0.0205 (12)0.0013 (10)0.0011 (9)0.0059 (10)
CB_170.0244 (14)0.0218 (14)0.0245 (13)0.0039 (11)0.0027 (11)0.0053 (11)
CG_170.0251 (15)0.0259 (15)0.0262 (14)0.0002 (12)0.0036 (12)0.0036 (12)
CD_170.0244 (15)0.0346 (17)0.0220 (13)0.0056 (13)0.0057 (11)0.0003 (12)
C_170.0201 (13)0.0215 (13)0.0167 (11)0.0044 (10)0.0013 (10)0.0066 (10)
O_170.0307 (13)0.0363 (14)0.0617 (17)0.0171 (11)0.0212 (12)0.0216 (13)
N_210.0211 (12)0.0289 (13)0.0148 (10)0.0005 (10)0.0040 (9)0.0030 (9)
CA_210.0229 (14)0.058 (2)0.0181 (13)0.0009 (15)0.0031 (11)0.0130 (14)
CB_210.0264 (16)0.056 (2)0.0304 (15)0.0005 (16)0.0026 (13)0.0153 (16)
CG2_210.0358 (19)0.067 (3)0.0386 (19)0.0175 (19)0.0063 (16)0.0095 (19)
CG1_210.0336 (18)0.044 (2)0.0298 (15)0.0049 (15)0.0011 (13)0.0013 (15)
CD_210.044 (2)0.044 (2)0.0431 (19)0.0036 (17)0.0167 (17)0.0001 (17)
C3_220.0193 (13)0.0325 (16)0.0159 (12)0.0088 (11)0.0056 (10)0.0046 (11)
N_220.0188 (12)0.0339 (14)0.0211 (11)0.0030 (10)0.0045 (9)0.0040 (10)
CA_220.0114 (11)0.0254 (14)0.0184 (12)0.0032 (10)0.0019 (9)0.0002 (11)
CB_220.0219 (13)0.0240 (14)0.0168 (11)0.0024 (11)0.0019 (10)0.0061 (11)
OG1_220.0276 (10)0.0279 (11)0.0150 (8)0.0016 (9)0.0032 (8)0.0010 (8)
CG2_220.0260 (14)0.0327 (16)0.0199 (12)0.0020 (13)0.0041 (11)0.0000 (12)
C_220.0194 (13)0.0294 (15)0.0185 (13)0.0013 (11)0.0004 (11)0.0023 (11)
O_220.0552 (17)0.0347 (13)0.0199 (10)0.0023 (12)0.0024 (10)0.0007 (9)
N_230.0335 (15)0.0286 (14)0.0211 (11)0.0008 (12)0.0030 (10)0.0044 (10)
CA_230.0239 (14)0.0267 (15)0.0126 (11)0.0032 (11)0.0003 (10)0.0023 (10)
CB_230.0211 (14)0.0220 (14)0.0314 (14)0.0049 (11)0.0058 (11)0.0012 (12)
CG_230.0194 (13)0.0291 (16)0.0298 (14)0.0011 (12)0.0094 (11)0.0001 (13)
CD1_230.0272 (15)0.0355 (17)0.0280 (14)0.0016 (13)0.0063 (12)0.0002 (13)
CE1_230.036 (2)0.044 (2)0.0381 (18)0.0077 (16)0.0122 (15)0.0171 (16)
CZ_230.0280 (17)0.0234 (16)0.060 (2)0.0018 (13)0.0161 (16)0.0077 (15)
CE2_230.037 (2)0.044 (2)0.045 (2)0.0067 (16)0.0066 (17)0.0135 (18)
CD2_230.0245 (15)0.0420 (19)0.0336 (16)0.0006 (14)0.0030 (13)0.0014 (15)
C_230.0209 (13)0.0191 (13)0.0221 (12)0.0033 (10)0.0004 (11)0.0027 (10)
O_230.0314 (12)0.0477 (15)0.0223 (10)0.0067 (11)0.0042 (9)0.0003 (10)
N_240.0206 (11)0.0215 (12)0.0173 (10)0.0006 (10)0.0008 (9)0.0013 (9)
CA_240.0255 (14)0.0181 (13)0.0120 (10)0.0002 (10)0.0015 (10)0.0014 (9)
CB_240.0222 (14)0.0190 (13)0.0265 (13)0.0036 (11)0.0002 (11)0.0039 (11)
CG_240.0193 (12)0.0286 (15)0.0219 (12)0.0033 (12)0.0004 (11)0.0078 (11)
CD_240.0241 (14)0.0222 (14)0.0150 (11)0.0002 (11)0.0008 (10)0.0009 (10)
C3_250.0227 (12)0.0214 (13)0.0111 (10)0.0053 (11)0.0076 (10)0.0047 (10)
N_250.0219 (11)0.0183 (11)0.0174 (10)0.0075 (9)0.0030 (9)0.0002 (8)
CA_250.0216 (13)0.0182 (13)0.0211 (13)0.0027 (11)0.0012 (10)0.0012 (10)
CB_250.0223 (13)0.0114 (12)0.0187 (12)0.0022 (9)0.0011 (10)0.0019 (9)
SG_250.0247 (3)0.0192 (3)0.0129 (3)0.0007 (3)0.0021 (2)0.0006 (2)
C_250.0212 (13)0.0210 (14)0.0189 (12)0.0058 (10)0.0001 (10)0.0018 (10)
O_250.0288 (11)0.0220 (10)0.0226 (10)0.0028 (9)0.0035 (8)0.0010 (8)
N_260.0243 (12)0.0105 (10)0.0231 (11)0.0005 (9)0.0015 (9)0.0037 (9)
CA_260.0215 (13)0.0177 (13)0.0164 (11)0.0022 (10)0.0008 (10)0.0006 (10)
CB_260.0175 (13)0.0309 (16)0.0263 (13)0.0002 (12)0.0007 (11)0.0012 (12)
CG_260.0113 (11)0.0342 (16)0.0186 (12)0.0011 (11)0.0027 (9)0.0068 (11)
CD1_260.0153 (13)0.0357 (17)0.0290 (15)0.0009 (12)0.0029 (11)0.0093 (13)
CE1_260.0257 (16)0.0341 (19)0.049 (2)0.0005 (14)0.0015 (15)0.0077 (16)
CZ_260.0189 (15)0.044 (2)0.055 (2)0.0002 (14)0.0051 (15)0.0137 (18)
CE2_260.0201 (15)0.053 (2)0.0274 (15)0.0027 (14)0.0006 (12)0.0027 (15)
CD2_260.0162 (12)0.0437 (18)0.0192 (12)0.0091 (13)0.0040 (10)0.0023 (13)
C_260.0193 (12)0.0216 (13)0.0166 (11)0.0027 (10)0.0011 (10)0.0034 (10)
O_260.0400 (13)0.0224 (11)0.0194 (9)0.0028 (9)0.0021 (9)0.0059 (8)
N_270.0218 (11)0.0146 (10)0.0168 (9)0.0019 (9)0.0009 (8)0.0014 (8)
CA_270.0131 (12)0.0160 (12)0.0192 (11)0.0045 (9)0.0011 (9)0.0053 (10)
CB_270.0244 (14)0.0183 (13)0.0311 (15)0.0021 (11)0.0012 (12)0.0044 (12)
CG_270.0278 (15)0.0269 (15)0.0177 (12)0.0006 (12)0.0029 (11)0.0034 (11)
CD_270.0329 (15)0.0223 (14)0.0179 (12)0.0053 (12)0.0093 (11)0.0043 (11)
C_270.0158 (13)0.0380 (17)0.0161 (11)0.0076 (12)0.0017 (10)0.0026 (11)
O_270.0244 (12)0.0611 (19)0.0477 (15)0.0042 (12)0.0062 (11)0.0339 (14)
O1_310.139 (5)0.066 (3)0.141 (4)0.056 (3)0.104 (4)0.053 (3)
C1_310.065 (4)0.091 (5)0.078 (4)0.016 (3)0.015 (3)0.027 (4)
C2_310.140 (7)0.077 (4)0.058 (3)0.020 (4)0.035 (4)0.006 (3)
N1_310.035 (2)0.112 (5)0.116 (4)0.026 (3)0.003 (2)0.076 (4)
C3_310.047 (3)0.041 (2)0.087 (4)0.000 (2)0.033 (3)0.006 (2)
C4_310.047 (3)0.058 (3)0.084 (4)0.007 (2)0.017 (3)0.020 (3)
Geometric parameters (Å, º) top
N_11—Ca_111.465 (4)Cb_21—Cg1_211.562 (6)
N_11—C_171.338 (4)Cb_21—H3_211.001
N_11—H1_110.881Cg2_21—H4_210.980
Ca_11—Cb_111.554 (4)Cg2_21—H5_210.979
Ca_11—C3_121.515 (4)Cg2_21—H6_210.981
Ca_11—H2_111.001Cg1_21—Cd_211.485 (6)
Cb_11—Cg2_111.521 (4)Cg1_21—H7_210.991
Cb_11—Cg1_111.531 (5)Cg1_21—H8_210.990
Cb_11—H3_110.999Cd_21—H9_210.980
Cg2_11—H4_110.980Cd_21—H10_210.981
Cg2_11—H5_110.980Cd_21—H11_210.980
Cg2_11—H6_110.980C3_22—N_221.260 (4)
Cg1_11—Cd_111.512 (5)C3_22—Og1_221.358 (4)
Cg1_11—H7_110.991N_22—Ca_221.463 (4)
Cg1_11—H8_110.991Ca_22—Cb_221.565 (4)
Cd_11—H9_110.980Ca_22—C_221.536 (5)
Cd_11—H10_110.979Ca_22—H1_221.000
Cd_11—H11_110.981Cb_22—Og1_221.470 (3)
C3_12—N_121.249 (4)Cb_22—Cg2_221.509 (4)
C3_12—Og1_121.365 (3)Cb_22—H2_221.000
N_12—Ca_121.477 (4)Cg2_22—H3_220.980
Ca_12—Cb_121.552 (4)Cg2_22—H4_220.980
Ca_12—C_121.526 (4)Cg2_22—H5_220.979
Ca_12—H1_121.000C_22—O_221.209 (4)
Cb_12—Og1_121.467 (3)C_22—N_231.342 (4)
Cb_12—Cg2_121.508 (4)N_23—Ca_231.441 (5)
Cb_12—H2_121.001 (3)N_23—H1_230.881
Cg2_12—H3_120.981Ca_23—Cb_231.549 (4)
Cg2_12—H4_120.980Ca_23—C_231.542 (4)
Cg2_12—H5_120.981Ca_23—H2_231.000
C_12—O_121.211 (4)Cb_23—Cg_231.510 (5)
C_12—N_131.352 (4)Cb_23—H3_230.988
N_13—Ca_131.459 (4)Cb_23—H4_230.991
N_13—H1_130.880Cg_23—Cd1_231.380 (5)
Ca_13—Cb_131.538 (5)Cg_23—Cd2_231.390 (5)
Ca_13—C_131.540 (4)Cd1_23—Ce1_231.389 (5)
Ca_13—H2_131.001Cd1_23—H5_230.950
Cb_13—Cg_131.529 (4)Ce1_23—Cz_231.355 (6)
Cb_13—H3_130.992Ce1_23—H6_230.950
Cb_13—H4_130.991Cz_23—Ce2_231.384 (6)
Cg_13—Cd1_131.374 (5)Cz_23—H7_230.950
Cg_13—Cd2_131.402 (4)Ce2_23—Cd2_231.388 (5)
Cd1_13—Ce1_131.407 (5)Ce2_23—H8_230.950
Cd1_13—H5_130.949Cd2_23—H9_230.951
Ce1_13—Cz_131.362 (5)C_23—O_231.216 (4)
Ce1_13—H6_130.949C_23—N_241.342 (4)
Cz_13—Ce2_131.407 (5)N_24—Ca_241.481 (4)
Cz_13—H7_130.951N_24—Cd_241.467 (3)
Ce2_13—Cd2_131.390 (5)Ca_24—Cb_241.551 (4)
Ce2_13—H8_130.952Ca_24—C3_251.515 (4)
Cd2_13—H9_130.950Ca_24—H1_241.001
C_13—O_131.227 (4)Cb_24—Cg_241.536 (4)
C_13—N_141.334 (4)Cb_24—H2_240.992
N_14—Ca_141.482 (4)Cb_24—H3_240.991
N_14—Cd_141.472 (4)Cg_24—Cd_241.524 (4)
Ca_14—Cb_141.537 (4)Cg_24—H4_240.990
Ca_14—C3_151.517 (4)Cg_24—H5_240.989
Ca_14—H1_140.998Cd_24—H6_240.992
Cb_14—Cg_141.543 (5)Cd_24—H7_240.989
Cb_14—H2_140.990C3_25—N_251.289 (4)
Cb_14—H3_140.990C3_25—Sg_251.741 (3)
Cg_14—Cd_141.526 (5)N_25—Ca_251.380 (4)
Cg_14—H4_140.991Ca_25—Cb_251.359 (4)
Cg_14—H5_140.989Ca_25—C_251.502 (4)
Cd_14—H6_140.992Cb_25—Sg_251.716 (3)
Cd_14—H7_140.991Cb_25—H1_250.949
C3_15—N_151.297 (4)C_25—O_251.233 (3)
C3_15—Sg_151.736 (3)C_25—N_261.337 (3)
N_15—Ca_151.365 (4)N_26—Ca_261.459 (3)
Ca_15—Cb_151.365 (4)N_26—H1_260.879
Ca_15—C_151.492 (4)Ca_26—Cb_261.569 (4)
Cb_15—Sg_151.721 (3)Ca_26—C_261.513 (4)
Cb_15—H1_150.948Ca_26—H2_260.999
C_15—O_151.229 (3)Cb_26—Cg_261.513 (5)
C_15—N_161.349 (4)Cb_26—H3_260.988
N_16—Ca_161.454 (4)Cb_26—H4_260.989
N_16—H1_160.880Cg_26—Cd1_261.399 (5)
Ca_16—C_161.528 (4)Cg_26—Cd2_261.397 (4)
Ca_16—Cb_161.560 (5)Cd1_26—Ce1_261.398 (5)
Ca_16—H2_161.001Cd1_26—H5_260.951
C_16—O_161.224 (3)Ce1_26—Cz_261.391 (6)
C_16—N_171.348 (4)Ce1_26—H6_260.949
Cb_16—Cg_161.512 (5)Cz_26—Ce2_261.382 (6)
Cb_16—H3_160.989Cz_26—H7_260.950
Cb_16—H4_160.988Ce2_26—Cd2_261.382 (5)
Cg_16—Cd1_161.365 (5)Ce2_26—H8_260.951
Cg_16—Cd2_161.386 (5)Cd2_26—H9_260.951
Cd1_16—Ce1_161.406 (6)C_26—O_261.229 (3)
Cd1_16—H5_160.949C_26—N_271.366 (4)
Ce1_16—Cz_161.397 (6)N_27—Ca_271.461 (4)
Ce1_16—H6_160.952N_27—Cd_271.487 (4)
Cz_16—Ce2_161.355 (7)Ca_27—Cb_271.539 (4)
Cz_16—H7_160.950Ca_27—C_271.552 (4)
Ce2_16—Cd2_161.385 (5)Ca_27—H1_271.001
Ce2_16—H8_160.952Cb_27—Cg_271.539 (5)
Cd2_16—H9_160.949Cb_27—H2_270.989
N_17—Ca_171.473 (4)Cb_27—H3_270.990
N_17—Cd_171.485 (4)Cg_27—Cd_271.539 (5)
Ca_17—Cb_171.526 (4)Cg_27—H4_270.988
Ca_17—C_171.537 (4)Cg_27—H5_270.990
Ca_17—H1_171.000Cd_27—H6_270.990
Cb_17—Cg_171.541 (4)Cd_27—H7_270.989
Cb_17—H2_170.990C_27—O_271.215 (5)
Cb_17—H3_170.989O1_31—C1_311.270 (9)
Cg_17—Cd_171.524 (5)C1_31—C2_311.461 (10)
Cg_17—H4_170.990C1_31—N1_311.298 (9)
Cg_17—H5_170.990C2_31—H1_310.980
Cd_17—H6_170.991C2_31—H2_310.982
Cd_17—H7_170.992C2_31—H3_310.980
C_17—O_171.213 (4)N1_31—C3_311.588 (9)
N_21—Ca_211.463 (4)N1_31—C4_311.491 (8)
N_21—C_271.327 (4)C3_31—H4_310.979
N_21—H1_210.881C3_31—H5_310.979
Ca_21—Cb_211.629 (6)C3_31—H6_310.979
Ca_21—C3_221.513 (5)C4_31—H7_310.980
Ca_21—H2_211.000C4_31—H8_310.982
Cb_21—Cg2_211.536 (6)C4_31—H9_310.979
Ca_11—N_11—C_17119.8 (2)Cg2_21—Cb_21—Cg1_21112.1 (3)
Ca_11—N_11—H1_11120.2Cg2_21—Cb_21—H3_21108.3
C_17—N_11—H1_11120.0Cg1_21—Cb_21—H3_21108.2
N_11—Ca_11—Cb_11113.4 (2)Cb_21—Cg2_21—H4_21109.4
N_11—Ca_11—C3_12109.6 (2)Cb_21—Cg2_21—H5_21109.6
N_11—Ca_11—H2_11108.1Cb_21—Cg2_21—H6_21109.5
Cb_11—Ca_11—C3_12109.4 (2)H4_21—Cg2_21—H5_21109.4
Cb_11—Ca_11—H2_11108.1H4_21—Cg2_21—H6_21109.4
C3_12—Ca_11—H2_11108.2H5_21—Cg2_21—H6_21109.5
Ca_11—Cb_11—Cg2_11109.3 (2)Cb_21—Cg1_21—Cd_21113.4 (3)
Ca_11—Cb_11—Cg1_11112.4 (2)Cb_21—Cg1_21—H7_21108.9
Ca_11—Cb_11—H3_11107.6Cb_21—Cg1_21—H8_21108.9
Cg2_11—Cb_11—Cg1_11112.3 (3)Cd_21—Cg1_21—H7_21108.9
Cg2_11—Cb_11—H3_11107.6Cd_21—Cg1_21—H8_21108.9
Cg1_11—Cb_11—H3_11107.5H7_21—Cg1_21—H8_21107.7
Cb_11—Cg2_11—H4_11109.3Cg1_21—Cd_21—H9_21109.5
Cb_11—Cg2_11—H5_11109.6Cg1_21—Cd_21—H10_21109.4
Cb_11—Cg2_11—H6_11109.5Cg1_21—Cd_21—H11_21109.4
H4_11—Cg2_11—H5_11109.6H9_21—Cd_21—H10_21109.6
H4_11—Cg2_11—H6_11109.5H9_21—Cd_21—H11_21109.4
H5_11—Cg2_11—H6_11109.3H10_21—Cd_21—H11_21109.5
Cb_11—Cg1_11—Cd_11114.2 (3)Ca_21—C3_22—N_22124.8 (3)
Cb_11—Cg1_11—H7_11108.7Ca_21—C3_22—Og1_22115.0 (2)
Cb_11—Cg1_11—H8_11108.7N_22—C3_22—Og1_22120.2 (3)
Cd_11—Cg1_11—H7_11108.7C3_22—N_22—Ca_22106.1 (2)
Cd_11—Cg1_11—H8_11108.7N_22—Ca_22—Cb_22105.8 (2)
H7_11—Cg1_11—H8_11107.7N_22—Ca_22—C_22113.6 (2)
Cg1_11—Cd_11—H9_11109.6N_22—Ca_22—H1_22109.2
Cg1_11—Cd_11—H10_11109.5Cb_22—Ca_22—C_22110.0 (2)
Cg1_11—Cd_11—H11_11109.4Cb_22—Ca_22—H1_22109.1
H9_11—Cd_11—H10_11109.4C_22—Ca_22—H1_22109.1
H9_11—Cd_11—H11_11109.6Ca_22—Cb_22—Og1_22101.9 (2)
H10_11—Cd_11—H11_11109.4Ca_22—Cb_22—Cg2_22116.0 (2)
Ca_11—C3_12—N_12126.6 (2)Ca_22—Cb_22—H2_22109.8
Ca_11—C3_12—Og1_12112.8 (2)Og1_22—Cb_22—Cg2_22109.1 (2)
N_12—C3_12—Og1_12120.4 (3)Og1_22—Cb_22—H2_22109.8
C3_12—N_12—Ca_12105.7 (2)Cg2_22—Cb_22—H2_22109.8
N_12—Ca_12—Cb_12105.8 (2)C3_22—Og1_22—Cb_22105.8 (2)
N_12—Ca_12—C_12112.8 (2)Cb_22—Cg2_22—H3_22109.4
N_12—Ca_12—H1_12109.3Cb_22—Cg2_22—H4_22109.5
Cb_12—Ca_12—C_12110.3 (2)Cb_22—Cg2_22—H5_22109.5
Cb_12—Ca_12—H1_12109.2H3_22—Cg2_22—H4_22109.4
C_12—Ca_12—H1_12109.2H3_22—Cg2_22—H5_22109.5
Ca_12—Cb_12—Og1_12102.4 (2)H4_22—Cg2_22—H5_22109.5
Ca_12—Cb_12—Cg2_12116.2 (2)Ca_22—C_22—O_22120.8 (3)
Ca_12—Cb_12—H2_12109.8Ca_22—C_22—N_23114.1 (3)
Og1_12—Cb_12—Cg2_12108.7 (2)O_22—C_22—N_23125.1 (3)
Og1_12—Cb_12—H2_12109.8C_22—N_23—Ca_23122.4 (3)
Cg2_12—Cb_12—H2_12109.7C_22—N_23—H1_23118.9
C3_12—Og1_12—Cb_12105.6 (2)Ca_23—N_23—H1_23118.8
Cb_12—Cg2_12—H3_12109.5N_23—Ca_23—Cb_23110.9 (3)
Cb_12—Cg2_12—H4_12109.3N_23—Ca_23—C_23106.2 (2)
Cb_12—Cg2_12—H5_12109.6N_23—Ca_23—H2_23109.8
H3_12—Cg2_12—H4_12109.5Cb_23—Ca_23—C_23110.2 (2)
H3_12—Cg2_12—H5_12109.4Cb_23—Ca_23—H2_23109.8
H4_12—Cg2_12—H5_12109.5C_23—Ca_23—H2_23109.8
Ca_12—C_12—O_12121.2 (3)Ca_23—Cb_23—Cg_23112.7 (2)
Ca_12—C_12—N_13115.2 (2)Ca_23—Cb_23—H3_23109.1
O_12—C_12—N_13123.6 (3)Ca_23—Cb_23—H4_23109.0
C_12—N_13—Ca_13122.2 (2)Cg_23—Cb_23—H3_23109.1
C_12—N_13—H1_13118.8Cg_23—Cb_23—H4_23109.1
Ca_13—N_13—H1_13118.9H3_23—Cb_23—H4_23107.8
N_13—Ca_13—Cb_13110.4 (2)Cb_23—Cg_23—Cd1_23121.0 (3)
N_13—Ca_13—C_13106.2 (2)Cb_23—Cg_23—Cd2_23120.1 (3)
N_13—Ca_13—H2_13110.2Cd1_23—Cg_23—Cd2_23118.9 (3)
Cb_13—Ca_13—C_13109.6 (3)Cg_23—Cd1_23—Ce1_23120.4 (3)
Cb_13—Ca_13—H2_13110.1Cg_23—Cd1_23—H5_23119.8
C_13—Ca_13—H2_13110.3Ce1_23—Cd1_23—H5_23119.8
Ca_13—Cb_13—Cg_13110.8 (2)Cd1_23—Ce1_23—Cz_23120.3 (4)
Ca_13—Cb_13—H3_13109.4Cd1_23—Ce1_23—H6_23119.8
Ca_13—Cb_13—H4_13109.4Cz_23—Ce1_23—H6_23119.9
Cg_13—Cb_13—H3_13109.5Ce1_23—Cz_23—Ce2_23120.5 (4)
Cg_13—Cb_13—H4_13109.4Ce1_23—Cz_23—H7_23119.8
H3_13—Cb_13—H4_13108.2Ce2_23—Cz_23—H7_23119.7
Cb_13—Cg_13—Cd1_13121.2 (3)Cz_23—Ce2_23—Cd2_23119.5 (4)
Cb_13—Cg_13—Cd2_13119.4 (3)Cz_23—Ce2_23—H8_23120.3
Cd1_13—Cg_13—Cd2_13119.3 (3)Cd2_23—Ce2_23—H8_23120.3
Cg_13—Cd1_13—Ce1_13120.3 (3)Cg_23—Cd2_23—Ce2_23120.3 (4)
Cg_13—Cd1_13—H5_13119.8Cg_23—Cd2_23—H9_23119.9
Ce1_13—Cd1_13—H5_13119.9Ce2_23—Cd2_23—H9_23119.8
Cd1_13—Ce1_13—Cz_13120.4 (4)Ca_23—C_23—O_23119.2 (2)
Cd1_13—Ce1_13—H6_13119.9Ca_23—C_23—N_24117.8 (2)
Cz_13—Ce1_13—H6_13119.7O_23—C_23—N_24122.9 (3)
Ce1_13—Cz_13—Ce2_13120.2 (4)C_23—N_24—Ca_24127.2 (2)
Ce1_13—Cz_13—H7_13120.0C_23—N_24—Cd_24119.7 (2)
Ce2_13—Cz_13—H7_13119.8Ca_24—N_24—Cd_24112.6 (2)
Cz_13—Ce2_13—Cd2_13119.2 (3)N_24—Ca_24—Cb_24101.3 (2)
Cz_13—Ce2_13—H8_13120.4N_24—Ca_24—C3_25110.3 (2)
Cd2_13—Ce2_13—H8_13120.3N_24—Ca_24—H1_24110.8
Cg_13—Cd2_13—Ce2_13120.5 (3)Cb_24—Ca_24—C3_25112.6 (2)
Cg_13—Cd2_13—H9_13119.8Cb_24—Ca_24—H1_24110.8
Ce2_13—Cd2_13—H9_13119.7C3_25—Ca_24—H1_24110.8
Ca_13—C_13—O_13119.0 (3)Ca_24—Cb_24—Cg_24103.0 (2)
Ca_13—C_13—N_14118.6 (3)Ca_24—Cb_24—H2_24111.1
O_13—C_13—N_14122.5 (3)Ca_24—Cb_24—H3_24111.2
C_13—N_14—Ca_14126.3 (3)Cg_24—Cb_24—H2_24111.2
C_13—N_14—Cd_14119.6 (3)Cg_24—Cb_24—H3_24111.2
Ca_14—N_14—Cd_14113.2 (3)H2_24—Cb_24—H3_24109.1
N_14—Ca_14—Cb_14101.8 (2)Cb_24—Cg_24—Cd_24103.3 (2)
N_14—Ca_14—C3_15109.3 (2)Cb_24—Cg_24—H4_24111.2
N_14—Ca_14—H1_14110.8Cb_24—Cg_24—H5_24111.0
Cb_14—Ca_14—C3_15112.6 (2)Cd_24—Cg_24—H4_24111.1
Cb_14—Ca_14—H1_14110.9Cd_24—Cg_24—H5_24111.2
C3_15—Ca_14—H1_14111.0H4_24—Cg_24—H5_24109.0
Ca_14—Cb_14—Cg_14104.1 (3)N_24—Cd_24—Cg_24104.2 (2)
Ca_14—Cb_14—H2_14111.0N_24—Cd_24—H6_24110.9
Ca_14—Cb_14—H3_14111.0N_24—Cd_24—H7_24110.9
Cg_14—Cb_14—H2_14110.8Cg_24—Cd_24—H6_24110.8
Cg_14—Cb_14—H3_14111.0Cg_24—Cd_24—H7_24110.9
H2_14—Cb_14—H3_14109.0H6_24—Cd_24—H7_24109.0
Cb_14—Cg_14—Cd_14103.0 (3)Ca_24—C3_25—N_25123.8 (2)
Cb_14—Cg_14—H4_14111.2Ca_24—C3_25—Sg_25121.64 (19)
Cb_14—Cg_14—H5_14111.1N_25—C3_25—Sg_25114.5 (2)
Cd_14—Cg_14—H4_14111.1C3_25—N_25—Ca_25110.4 (2)
Cd_14—Cg_14—H5_14111.2N_25—Ca_25—Cb_25116.4 (2)
H4_14—Cg_14—H5_14109.0N_25—Ca_25—C_25120.2 (2)
N_14—Cd_14—Cg_14103.5 (3)Cb_25—Ca_25—C_25123.4 (2)
N_14—Cd_14—H6_14111.1Ca_25—Cb_25—Sg_25108.88 (19)
N_14—Cd_14—H7_14111.2Ca_25—Cb_25—H1_25125.5
Cg_14—Cd_14—H6_14111.1Sg_25—Cb_25—H1_25125.7
Cg_14—Cd_14—H7_14111.1C3_25—Sg_25—Cb_2589.61 (13)
H6_14—Cd_14—H7_14108.9Ca_25—C_25—O_25121.3 (2)
Ca_14—C3_15—N_15123.9 (2)Ca_25—C_25—N_26114.2 (2)
Ca_14—C3_15—Sg_15121.9 (2)O_25—C_25—N_26124.5 (3)
N_15—C3_15—Sg_15114.2 (2)C_25—N_26—Ca_26121.5 (2)
C3_15—N_15—Ca_15110.9 (2)C_25—N_26—H1_26119.2
N_15—Ca_15—Cb_15116.6 (3)Ca_26—N_26—H1_26119.3
N_15—Ca_15—C_15119.9 (2)N_26—Ca_26—Cb_26109.2 (2)
Cb_15—Ca_15—C_15123.4 (3)N_26—Ca_26—C_26107.4 (2)
Ca_15—Cb_15—Sg_15108.6 (2)N_26—Ca_26—H2_26110.6
Ca_15—Cb_15—H1_15125.6Cb_26—Ca_26—C_26108.5 (2)
Sg_15—Cb_15—H1_15125.7Cb_26—Ca_26—H2_26110.5
C3_15—Sg_15—Cb_1589.68 (13)C_26—Ca_26—H2_26110.5
Ca_15—C_15—O_15122.6 (2)Ca_26—Cb_26—Cg_26112.2 (2)
Ca_15—C_15—N_16113.1 (2)Ca_26—Cb_26—H3_26109.2
O_15—C_15—N_16124.3 (3)Ca_26—Cb_26—H4_26109.2
C_15—N_16—Ca_16122.4 (2)Cg_26—Cb_26—H3_26109.1
C_15—N_16—H1_16118.8Cg_26—Cb_26—H4_26109.2
Ca_16—N_16—H1_16118.9H3_26—Cb_26—H4_26107.8
N_16—Ca_16—C_16105.8 (2)Cb_26—Cg_26—Cd1_26120.4 (3)
N_16—Ca_16—Cb_16111.5 (2)Cb_26—Cg_26—Cd2_26120.8 (3)
N_16—Ca_16—H2_16109.8Cd1_26—Cg_26—Cd2_26118.8 (3)
C_16—Ca_16—Cb_16109.8 (2)Cg_26—Cd1_26—Ce1_26120.2 (3)
C_16—Ca_16—H2_16109.9Cg_26—Cd1_26—H5_26119.8
Cb_16—Ca_16—H2_16109.9Ce1_26—Cd1_26—H5_26120.0
Ca_16—C_16—O_16119.3 (2)Cd1_26—Ce1_26—Cz_26119.9 (4)
Ca_16—C_16—N_17119.7 (3)Cd1_26—Ce1_26—H6_26120.2
O_16—C_16—N_17120.9 (3)Cz_26—Ce1_26—H6_26120.0
Ca_16—Cb_16—Cg_16112.3 (3)Ce1_26—Cz_26—Ce2_26120.1 (4)
Ca_16—Cb_16—H3_16109.2Ce1_26—Cz_26—H7_26120.0
Ca_16—Cb_16—H4_16109.2Ce2_26—Cz_26—H7_26119.9
Cg_16—Cb_16—H3_16109.1Cz_26—Ce2_26—Cd2_26120.2 (4)
Cg_16—Cb_16—H4_16109.1Cz_26—Ce2_26—H8_26119.8
H3_16—Cb_16—H4_16107.8Cd2_26—Ce2_26—H8_26120.0
Cb_16—Cg_16—Cd1_16120.9 (3)Cg_26—Cd2_26—Ce2_26120.9 (3)
Cb_16—Cg_16—Cd2_16119.6 (3)Cg_26—Cd2_26—H9_26119.6
Cd1_16—Cg_16—Cd2_16119.5 (3)Ce2_26—Cd2_26—H9_26119.5
Cg_16—Cd1_16—Ce1_16120.4 (3)Ca_26—C_26—O_26119.9 (2)
Cg_16—Cd1_16—H5_16119.7Ca_26—C_26—N_27118.7 (2)
Ce1_16—Cd1_16—H5_16119.9O_26—C_26—N_27121.3 (2)
Cd1_16—Ce1_16—Cz_16119.1 (4)C_26—N_27—Ca_27127.8 (2)
Cd1_16—Ce1_16—H6_16120.5C_26—N_27—Cd_27119.0 (2)
Cz_16—Ce1_16—H6_16120.5Ca_27—N_27—Cd_27112.6 (2)
Ce1_16—Cz_16—Ce2_16120.0 (4)N_27—Ca_27—Cb_27102.3 (2)
Ce1_16—Cz_16—H7_16120.0N_27—Ca_27—C_27113.3 (2)
Ce2_16—Cz_16—H7_16119.9N_27—Ca_27—H1_27110.0
Cz_16—Ce2_16—Cd2_16120.6 (4)Cb_27—Ca_27—C_27111.1 (2)
Cz_16—Ce2_16—H8_16119.8Cb_27—Ca_27—H1_27110.0
Cd2_16—Ce2_16—H8_16119.6C_27—Ca_27—H1_27110.0
Cg_16—Cd2_16—Ce2_16120.4 (3)Ca_27—Cb_27—Cg_27103.2 (2)
Cg_16—Cd2_16—H9_16119.8Ca_27—Cb_27—H2_27111.1
Ce2_16—Cd2_16—H9_16119.8Ca_27—Cb_27—H3_27111.1
C_16—N_17—Ca_17128.0 (2)Cg_27—Cb_27—H2_27111.2
C_16—N_17—Cd_17119.6 (2)Cg_27—Cb_27—H3_27111.2
Ca_17—N_17—Cd_17111.4 (2)H2_27—Cb_27—H3_27109.1
N_17—Ca_17—Cb_17102.4 (2)Cb_27—Cg_27—Cd_27103.5 (3)
N_17—Ca_17—C_17113.6 (2)Cb_27—Cg_27—H4_27110.9
N_17—Ca_17—H1_17110.1Cb_27—Cg_27—H5_27111.1
Cb_17—Ca_17—C_17110.1 (2)Cd_27—Cg_27—H4_27111.1
Cb_17—Ca_17—H1_17110.1Cd_27—Cg_27—H5_27111.1
C_17—Ca_17—H1_17110.2H4_27—Cg_27—H5_27109.0
Ca_17—Cb_17—Cg_17103.7 (2)N_27—Cd_27—Cg_27103.4 (2)
Ca_17—Cb_17—H2_17111.0N_27—Cd_27—H6_27111.0
Ca_17—Cb_17—H3_17111.1N_27—Cd_27—H7_27111.0
Cg_17—Cb_17—H2_17111.0Cg_27—Cd_27—H6_27111.1
Cg_17—Cb_17—H3_17111.0Cg_27—Cd_27—H7_27111.1
H2_17—Cb_17—H3_17109.0H6_27—Cd_27—H7_27109.1
Cb_17—Cg_17—Cd_17102.7 (3)N_21—C_27—Ca_27116.8 (2)
Cb_17—Cg_17—H4_17111.2N_21—C_27—O_27124.2 (3)
Cb_17—Cg_17—H5_17111.3Ca_27—C_27—O_27119.0 (3)
Cd_17—Cg_17—H4_17111.2O1_31—C1_31—C2_31134.4 (7)
Cd_17—Cg_17—H5_17111.2O1_31—C1_31—N1_31114.5 (6)
H4_17—Cg_17—H5_17109.3C2_31—C1_31—N1_31110.8 (6)
N_17—Cd_17—Cg_17104.6 (3)C1_31—C2_31—H1_31109.5
N_17—Cd_17—H6_17110.9C1_31—C2_31—H2_31109.5
N_17—Cd_17—H7_17110.9C1_31—C2_31—H3_31109.5
Cg_17—Cd_17—H6_17110.8H1_31—C2_31—H2_31109.4
Cg_17—Cd_17—H7_17110.8H1_31—C2_31—H3_31109.5
H6_17—Cd_17—H7_17108.7H2_31—C2_31—H3_31109.5
N_11—C_17—Ca_17117.9 (2)C1_31—N1_31—C3_31118.0 (5)
N_11—C_17—O_17122.5 (3)C1_31—N1_31—C4_31130.2 (5)
Ca_17—C_17—O_17119.6 (3)C3_31—N1_31—C4_31111.0 (5)
Ca_21—N_21—C_27122.1 (3)N1_31—C3_31—H4_31109.4
Ca_21—N_21—H1_21119.0N1_31—C3_31—H5_31109.4
C_27—N_21—H1_21118.9N1_31—C3_31—H6_31109.6
N_21—Ca_21—Cb_21108.2 (3)H4_31—C3_31—H5_31109.6
N_21—Ca_21—C3_22109.5 (3)H4_31—C3_31—H6_31109.4
N_21—Ca_21—H2_21111.0H5_31—C3_31—H6_31109.5
Cb_21—Ca_21—C3_22106.2 (3)N1_31—C4_31—H7_31109.4
Cb_21—Ca_21—H2_21110.9N1_31—C4_31—H8_31109.4
C3_22—Ca_21—H2_21110.9N1_31—C4_31—H9_31109.5
Ca_21—Cb_21—Cg2_21111.1 (3)H7_31—C4_31—H8_31109.5
Ca_21—Cb_21—Cg1_21108.6 (3)H7_31—C4_31—H9_31109.6
Ca_21—Cb_21—H3_21108.4H8_31—C4_31—H9_31109.4

Experimental details

Crystal data
Chemical formulaC41H49N7O6S·0.5C4H9NO
Mr811.51
Crystal system, space groupOrthorhombic, P212121
Temperature (K)90
a, b, c (Å)12.6034 (7), 12.6075 (7), 53.536 (3)
V3)8506.7 (8)
Z8
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.45 × 0.30 × 0.10
Data collection
DiffractometerBruker AXS SMART APEX area detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.883, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
102830, 20493, 20401
Rint0.038
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.127, 1.16
No. of reflections20493
No. of parameters1046
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.86, 0.27
Absolute structure(Flack, 1983), 8904 Friedel pairs
Absolute structure parameter0.09 (6)

Computer programs: SMART (Bruker, 1998), SAINTPLUS (Bruker, 1998), SHELXD (Seldrick & Gould, 1996), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PARST (Nardelli, 1983).

Selected torsion angles (°). The ϕ, ψ and ω angles of peptide backbone represent torsion angles of –C-N-Cα-C–, –N-Cα-C-N– and –Cα-C-N-Cα- bonds, respectively. top
anglemolecule 1molecule 2
Ile1
ϕ1-97.1 (3)-83.0 (4)
ψ1-19.4 (4)-32.8 (5)
ω1-174.9 (2)-174.3 (3)
Oxz2
ϕ2120.6 (3)121.7 (3)
ψ20.9 (3)-4.8 (4)
ω2-175.9 (2)-178.3 (3)
Phe3
ϕ3-162.8 (3)-154.0 (3)
ψ3109.6 (3)104.2 (3)
ω3-7.2 (5)0.5 (4)
Pro4
ϕ4-62.5 (4)-71.1 (3)
ψ4-34.5 (4)-31.2 (4)
ω4-179.3 (3)-178.9 (2)
Thz5
ϕ5-175.1 (3)-176.2 (2)
ψ5-0.1 (4)-1.1 (4)
ω5172.9 (3)171.7 (2)
Phe6
ϕ6-164.0 (3)-165.8 (2)
ψ6139.8 (3)141.4 (2)
ω60.6 (4)-4.2 (4)
Pro7
ϕ7-92.4 (3)-89.2 (3)
ψ7-7.8 (3)-11.8 (4)
ω7177.0 (2)177.0 (3)
 

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