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In the crystal structure of the tetrapeptide Boc0–Gly1–ΔPhe2–Gly3–Phe4p-NA (p-NA is para-nitro­aniline), C33H36N6O8, there are two independent mol­ecules differing in conformation in the asymmetric part of the unit cell. All the amino acids in the peptide are linked trans to each other. The torsion angles in the main chain of both mol­ecules are close to the values of the type β-II turn. Two intramolecular and three intermolecular N—H...O hydrogen bonds stabilize the conformation of each of the mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100017753/gd1118sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100017753/gd1118Isup2.hkl
Contains datablock I

CCDC reference: 160007

Comment top

The α, β–dehydroaminoacid residues have been found to occur naturally in several microbial peptides and antibiotics (Noda et al., 1983; Spatola, 1983). Their presence in peptides confers increased resistance to enzymatic degradation and for this reason many highly active analogues of bioactive peptides have been designed and synthesized (Fisher et al., 1981; Costa et al., 1983; Sharma & Chauhan, 1988). In particular, α,β–dehydrophenylalanine (ΔPhe) residues exhibit preferential secondary structural features both in the solid state and in solution. Determination of the crystal and molecular structure of many ΔPhe containing peptides has provided evidence that ΔPhe is strong inducer of β–bends (Venkatachalam, 1968) in short sequences with single ΔPhe residue (Główka et al., 1987; Główka, 1988; Aubry et al., 1991) and of 310–helical structures in long sequences (Rajashankar et al., 1992; Padmanabhan & Singh, 1993; Rajashankar, Ramakumar, Jain & Chauhan et al., 1995; Rajashankar, Ramakumar, Mal et al., 1995; Jain, 1997). Additionally, the final conformation of any ΔPhe peptide depends upon the number and position of ΔPhe residues as well as the nature of the amino acids flanking them (Rajashankar et al., 1996).

Here we present the crystal structure of a tetrapeptide containing one ΔZPhe between two flexible glycine residues and one phenylalanine, Boc0–Gly1–ΔPhe2–Gly3–Phe4–p–NA (p–NA is para–nitroaniline), (I). In the independent part of the unit cell there are two independent molecules (A and B) differing in conformation (Fig. 1). The bond lengths and bond angles for both molecules are the same within 5 σ, and selected parameters there are in Table 1. \sch

The CαCβ (C8—C9 and C8'—C9') distances for the ΔPhe in A and B agree well with the standard double bond distance observed in the structures containing ΔPhe residues (e.g. Główka, 1988). The conjugation of the aromatic ring with the CαCβ bond is extended to the N—Cα (N2—C8 and N2'—C8') and Cα—C (C8—C16 and C8'—C16') bonds. It leads to the shortening of about 0.35 Å for N—Cα and 0.55 Å for Cα—C bonds in respect to the corresponding bonds in saturated Phe4 unit (N4—C19, N4'—C19', C19—C27 and C19'—C27'). The steric contacts between the side-chain and main-chain atoms of the ΔPhe residue are partly relaxed by rearrangement of bond angles at Cα and Cβ atoms. For example, the N—CαCβ (N2—C8—C9 and N2'—C8'—C9') angles are increased from the value of 120°, ca 4°, whereas the CβCα—C (C9—C8—C16 and C9'—C8'—C16') angles are reduced of ca 2°. Similar effects are observed in Boc–Val–ΔPhe–ΔPhe–ΔPhe–Val–OMe (Jain, 1997).

All the amino acids in the peptide are linked trans to each other with the deviation of ω from 180° of less than ca 6° [with the exception of 11.8 (2)° for ω4 for the A molecule]. The torsion angles in the main chains of both molecules and the (Φ/Ψ) of Gly1 and ΔZPhe2 approximate the values assigned to the amino acid residues in the corners of a type II β–turn. The intramolecular hydrogen bonds between the amide (N3 and N3') of Gly3 and the carboxyl (O2 and O2') of the Boc groups are similar to those observed in Boc–Gly–ΔPhe–Gly–OMe (Główka, 1988). The torsion angles χ1 [-7.4 (4) and 9.2 (4)°], χ2,1 [-27.9 (4) and 29.5 (4)°] and χ2,2 [155.0 (2) and -154.1 (2)°] of the ΔPhe suggest that the side chains in A and B molecules are planar.

The two Gly residues adopt a conformation known as a polyglycine helix (Walton, 1981) with Φ and Ψ close to 80 and -150°. The relative inclination of the planes of two Gly units are 37.5 (3)° for A and 31.5 (3)° for B. The torsion angles for the Boc group ω0 and Φ0 in both molecules (A and B) correspond to a trans–trans conformation. This makes it possible for O2 (Boc) atoms to take part in the intramolecular N3—H3D···O2 hydrogen bond (Table 2). The carbonyl oxygen of ΔPhe2 takes part in another intramolecular hydrogen bond with the amide group of p–NA. Those two intramolecular hydrogen bonds stabilize the conformation of both molecules. Each of the molecules is connected to three others by N—H···O hydrogen bonds of medium strength.

Related literature top

For related literature, see: Aubry et al. (1991); Costa et al. (1983); Fisher et al. (1981); Główka (1988); Główka et al. (1987); Jain et al. (1997); Makowski et al. (2000); Noda et al. (1983); Padmanabhan & Singh (1993); Rajashankar et al. (1992, 1996); Rajashankar, Ramakumar, Jain & Chauhan (1995); Rajashankar, Ramakumar, Mal, Jain & Chauhan (1995); Sharma & Chauhan (1988); Spatola (1983); Venkatachalam (1968); Walton (1981).

Experimental top

Boc–Gly–ΔPhe–Gly–Phe–p–NA was synthesized by the method described earlier (Makowski et al., 2000). Crystals suitable for X–ray structure analysis were grown from the ethyl acetate–diethyl ether (1:1)/hexane solution.

Refinement top

The structure is non-centrosymmetric since both molecules have the same configuration (S on carbon c19 and c19'). The refinement in centrosymmetric P1 space group was tried and gave R ca 12%. In the absence of any significant anomalous scatterers, the Friedel equivalents were merged and the absolute configuration set by reference is that of natural phenylalanine. H atoms were treated as riding with N—H 0.90 Å, C—H 0.96 Å.

Computing details top

Data collection: KUMA Diffraction Software (KUMA, 1998); cell refinement: KUMA Diffraction Software; data reduction: KUMA Diffraction Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 199b); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structures (molecule A and B) of Boc–Gly–ΔPhe- Gly–Phe–p–NA. Displacement ellipsoids are shown at the 50% level. Dashed lines indicate intramolecular hydrogen bonds.
(I) top
Crystal data top
C33H36N6O8Z = 2
Mr = 644.68F(000) = 680
Triclinic, P1Dx = 1.323 Mg m3
a = 10.328 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.605 (2) ÅCell parameters from 29 reflections
c = 14.796 (3) Åθ = 5–12°
α = 70.00 (3)°µ = 0.10 mm1
β = 86.37 (3)°T = 105 K
γ = 76.19 (3)°Plate, yellow
V = 1617.9 (5) Å30.5 × 0.4 × 0.3 mm
Data collection top
KUMA KM–4
diffractometer
Rint = 0.029
Radiation source: fine-focus sealed tubeθmax = 26.1°, θmin = 1.5°
Graphite monochromatorh = 1212
ω scansk = 1312
11299 measured reflectionsl = 1616
5804 independent reflections2 standard reflections every 50 reflections
5429 reflections with I > 2σ(I) intensity decay: 0.3%
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)] = 0.032H-atom parameters constrained
wR(F2) = 0.105Calculated w = 1/[σ2(Fo2) + (0.0814P)2 + 0.1142P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.011
5804 reflectionsΔρmax = 0.27 e Å3
847 parametersΔρmin = 0.37 e Å3
3 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods
Crystal data top
C33H36N6O8γ = 76.19 (3)°
Mr = 644.68V = 1617.9 (5) Å3
Triclinic, P1Z = 2
a = 10.328 (2) ÅMo Kα radiation
b = 11.605 (2) ŵ = 0.10 mm1
c = 14.796 (3) ÅT = 105 K
α = 70.00 (3)°0.5 × 0.4 × 0.3 mm
β = 86.37 (3)°
Data collection top
KUMA KM–4
diffractometer
Rint = 0.029
11299 measured reflections2 standard reflections every 50 reflections
5804 independent reflections intensity decay: 0.3%
5429 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0323 restraints
wR(F2) = 0.105H-atom parameters constrained
S = 1.02Δρmax = 0.27 e Å3
5804 reflectionsΔρmin = 0.37 e Å3
847 parametersAbsolute structure: Flack (1983)
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
O10.6678 (2)0.48239 (18)0.85623 (15)0.0261 (4)
O20.64381 (19)0.28032 (18)0.89527 (14)0.0231 (4)
O30.75597 (17)0.21362 (16)1.10279 (14)0.0204 (4)
O40.96448 (17)0.11258 (17)1.11484 (13)0.0195 (4)
O50.92384 (18)0.19111 (18)0.93694 (14)0.0234 (4)
O61.2760 (2)0.49850 (19)1.06290 (16)0.0308 (5)
O71.0028 (4)0.5612 (3)1.5550 (2)0.0590 (8)
O81.0491 (4)0.7348 (3)1.5246 (2)0.0625 (9)
N10.5562 (2)0.4010 (2)0.98608 (17)0.0208 (5)
H1A0.53210.47900.98970.025*
N20.6310 (2)0.0724 (2)1.12064 (16)0.0185 (5)
H2D0.54930.05971.11640.022*
N30.8351 (2)0.0262 (2)0.99107 (16)0.0190 (5)
H3D0.75540.07760.96830.023*
N41.1315 (2)0.1684 (2)0.94200 (16)0.0189 (5)
H4D1.18570.11890.94390.023*
N51.1403 (2)0.3513 (2)1.11740 (17)0.0215 (5)
H5A1.10310.26821.09990.026*
N61.0384 (3)0.6216 (3)1.5004 (2)0.0427 (7)
C10.7438 (3)0.4809 (3)0.7686 (2)0.0287 (6)
C20.6528 (4)0.4781 (3)0.6940 (2)0.0401 (8)
H2A0.57680.54800.68240.048*
H2B0.70020.48360.63530.048*
H2C0.62370.40070.71690.048*
C30.7834 (4)0.6071 (3)0.7361 (3)0.0420 (8)
H3A0.70470.67450.72150.050*
H3B0.83390.61150.78660.050*
H3C0.83680.61460.67980.050*
C40.8680 (3)0.3741 (3)0.7920 (3)0.0379 (8)
H4A0.84200.29510.81240.045*
H4B0.92150.38120.73580.045*
H4C0.91860.37810.84260.045*
C50.6243 (3)0.3792 (2)0.9112 (2)0.0208 (6)
C60.5219 (3)0.2948 (2)1.0608 (2)0.0209 (5)
H6A0.45900.26351.03600.025*
H6B0.48140.32101.11290.025*
C70.6473 (2)0.1909 (2)1.09708 (19)0.0178 (5)
C80.7414 (2)0.0328 (2)1.15171 (19)0.0176 (5)
C90.7452 (3)0.1302 (3)1.2335 (2)0.0195 (5)
H9A0.82090.19981.24200.023*
C100.6493 (3)0.1451 (2)1.31214 (19)0.0201 (5)
C110.5685 (3)0.0447 (3)1.3351 (2)0.0238 (6)
H11A0.56990.04031.29600.029*
C120.4859 (3)0.0665 (3)1.4138 (2)0.0286 (6)
H12A0.43280.00351.42990.034*
C130.4789 (3)0.1888 (3)1.4696 (2)0.0307 (6)
H13A0.42060.20331.52350.037*
C140.5573 (3)0.2886 (3)1.4463 (2)0.0307 (7)
H14A0.55210.37321.48340.037*
C150.6438 (3)0.2678 (3)1.3696 (2)0.0259 (6)
H15A0.70040.33831.35590.031*
C160.8542 (3)0.0404 (2)1.08456 (19)0.0169 (5)
C170.9459 (3)0.0139 (2)0.9264 (2)0.0203 (5)
H17A1.01550.04640.94190.024*
H17B0.91670.06200.86120.024*
C180.9993 (2)0.1239 (2)0.93622 (18)0.0180 (5)
C191.1872 (3)0.2971 (2)0.94487 (19)0.0195 (5)
H19A1.12300.31950.91380.023*
C201.3144 (3)0.3058 (3)0.8864 (2)0.0230 (6)
H20A1.33850.38750.87950.028*
H20B1.38530.29840.92140.028*
C211.3013 (3)0.2058 (3)0.7872 (2)0.0239 (6)
C221.1854 (3)0.1610 (3)0.7320 (2)0.0360 (7)
H22A1.11020.19750.75440.043*
C231.1765 (3)0.0634 (4)0.6445 (2)0.0430 (9)
H23A1.09520.03350.60690.052*
C241.2828 (4)0.0094 (3)0.6110 (2)0.0396 (8)
H24A1.27490.06010.55160.047*
C251.4008 (4)0.0552 (3)0.6638 (2)0.0380 (8)
H25A1.47680.02040.64020.046*
C261.4091 (3)0.1525 (3)0.7507 (2)0.0301 (6)
H26A1.49150.18410.78710.036*
C271.2074 (3)0.3924 (3)1.0477 (2)0.0217 (6)
C281.1219 (3)0.4242 (3)1.2139 (2)0.0217 (6)
C291.0882 (3)0.3615 (3)1.2801 (2)0.0253 (6)
H29A1.08330.27271.26030.030*
C301.0620 (3)0.4258 (3)1.3743 (2)0.0289 (6)
H30A1.03910.38261.42010.035*
C311.0694 (3)0.5534 (3)1.4009 (2)0.0320 (7)
C321.1042 (4)0.6176 (3)1.3375 (2)0.0362 (7)
H32A1.11040.70671.35830.043*
C331.1301 (3)0.5527 (3)1.2421 (2)0.0312 (7)
H33A1.15360.59651.19670.037*
O1'0.6586 (2)0.37360 (18)0.26175 (15)0.0264 (4)
O2'0.6904 (2)0.57357 (19)0.22206 (14)0.0269 (4)
O3'0.55904 (18)0.62678 (17)0.02787 (14)0.0216 (4)
O4'0.33376 (17)0.93925 (16)0.00879 (13)0.0188 (4)
O5'0.35743 (17)1.05629 (17)0.15589 (14)0.0202 (4)
O6'0.0685 (2)1.34365 (19)0.04303 (16)0.0319 (5)
O7'0.3312 (3)1.4137 (3)0.4518 (2)0.0592 (8)
O8'0.3110 (3)1.5789 (3)0.4111 (2)0.0522 (7)
N1'0.7724 (2)0.4505 (2)0.13141 (17)0.0208 (5)
H1'A0.80000.37160.12980.025*
N2'0.6757 (2)0.7780 (2)0.01392 (16)0.0192 (5)
H2'D0.75680.79510.01790.023*
N3'0.4731 (2)0.8286 (2)0.11702 (16)0.0194 (5)
H3'D0.55620.78760.14000.023*
N4'0.1611 (2)1.0054 (2)0.15114 (16)0.0178 (4)
H4'D0.12160.94440.15040.021*
N5'0.1740 (2)1.1927 (2)0.02007 (16)0.0201 (5)
H5'A0.19871.10860.00600.024*
N6'0.3068 (3)1.4684 (3)0.3931 (2)0.0390 (7)
C1'0.5749 (3)0.3806 (3)0.3453 (2)0.0278 (6)
C2'0.6605 (4)0.3823 (3)0.4236 (2)0.0384 (8)
H2'A0.73370.30950.43930.046*
H2'B0.69420.45720.40190.046*
H2'C0.60780.38080.47970.046*
C3'0.4562 (3)0.4928 (3)0.3153 (2)0.0333 (7)
H3'A0.48660.56950.29630.040*
H3'B0.40950.49000.26230.040*
H3'C0.39730.48960.36860.040*
C4'0.5268 (4)0.2591 (3)0.3752 (3)0.0406 (8)
H4'A0.60210.18840.39400.049*
H4'B0.46790.25580.42840.049*
H4'C0.48020.25620.32220.049*
C5'0.7055 (3)0.4741 (2)0.20734 (19)0.0210 (6)
C6'0.7977 (3)0.5582 (3)0.0533 (2)0.0227 (6)
H6'A0.83570.53220.00050.027*
H6'B0.85990.59410.07420.027*
C7'0.6661 (3)0.6563 (2)0.02113 (19)0.0180 (5)
C8'0.5625 (3)0.8791 (2)0.0441 (2)0.0187 (5)
C9'0.5566 (3)0.9801 (3)0.12358 (19)0.0206 (5)
H9'A0.47881.04710.12970.025*
C10'0.6501 (3)1.0047 (3)0.2026 (2)0.0213 (6)
C11'0.7322 (3)0.9106 (3)0.2318 (2)0.0240 (6)
H11B0.73410.82380.19610.029*
C12'0.8119 (3)0.9404 (3)0.3118 (2)0.0288 (6)
H12B0.86600.87460.33240.035*
C13'0.8133 (3)1.0649 (3)0.3623 (2)0.0333 (7)
H13B0.86891.08540.41730.040*
C14'0.7349 (3)1.1593 (3)0.3330 (2)0.0322 (7)
H14B0.73781.24550.36670.039*
C15'0.6515 (3)1.1300 (3)0.2550 (2)0.0265 (6)
H15B0.59441.19670.23690.032*
C16'0.4487 (3)0.8813 (2)0.02270 (19)0.0183 (5)
C17'0.3628 (3)0.8389 (2)0.1823 (2)0.0199 (5)
H17C0.39540.80180.24770.024*
H17D0.30010.79410.17370.024*
C18'0.2944 (2)0.9770 (2)0.16192 (18)0.0170 (5)
C19'0.0775 (2)1.1295 (2)0.14051 (19)0.0185 (5)
H19B0.01201.12480.13130.022*
C20'0.0765 (3)1.1634 (3)0.2319 (2)0.0221 (5)
H20C0.01411.24250.22350.026*
H20D0.16341.17280.24300.026*
C21'0.0384 (3)1.0621 (3)0.3184 (2)0.0227 (6)
C22'0.1355 (3)0.9589 (3)0.3704 (2)0.0293 (6)
H22B0.22770.95550.35490.035*
C23'0.1005 (4)0.8602 (3)0.4448 (2)0.0373 (7)
H23B0.16850.78880.47960.045*
C24'0.0307 (4)0.8646 (3)0.4688 (2)0.0363 (7)
H24B0.05480.79620.51980.044*
C25'0.1285 (3)0.9680 (3)0.4191 (2)0.0351 (7)
H25B0.22030.97230.43650.042*
C26'0.0938 (3)1.0662 (3)0.3436 (2)0.0284 (6)
H26B0.16231.13730.30910.034*
C27'0.1087 (3)1.2343 (3)0.0505 (2)0.0211 (6)
C28'0.2067 (3)1.2663 (3)0.1123 (2)0.0216 (6)
C29'0.2286 (3)1.2102 (3)0.1830 (2)0.0244 (6)
H29B0.22051.12490.16750.029*
C30'0.2615 (3)1.2759 (3)0.2752 (2)0.0277 (6)
H30B0.27701.23700.32390.033*
C31'0.2718 (3)1.3985 (3)0.2954 (2)0.0298 (7)
C32'0.2516 (3)1.4561 (3)0.2264 (2)0.0327 (7)
H32B0.26011.54140.24250.039*
C33'0.2187 (3)1.3898 (3)0.1334 (2)0.0282 (6)
H33B0.20461.42880.08480.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0330 (11)0.0168 (10)0.0274 (11)0.0071 (8)0.0067 (8)0.0061 (8)
O20.0283 (10)0.0152 (10)0.0248 (10)0.0029 (7)0.0017 (8)0.0069 (7)
O30.0166 (9)0.0148 (9)0.0285 (10)0.0020 (7)0.0011 (7)0.0070 (7)
O40.0159 (9)0.0157 (9)0.0240 (9)0.0004 (7)0.0008 (7)0.0052 (7)
O50.0165 (9)0.0217 (10)0.0339 (11)0.0051 (7)0.0017 (8)0.0116 (8)
O60.0296 (11)0.0168 (10)0.0379 (12)0.0008 (8)0.0084 (9)0.0045 (9)
O70.092 (2)0.0437 (16)0.0324 (14)0.0080 (15)0.0200 (14)0.0101 (12)
O80.112 (3)0.0268 (14)0.0399 (15)0.0199 (15)0.0161 (15)0.0003 (11)
N10.0213 (11)0.0130 (11)0.0247 (12)0.0011 (8)0.0010 (9)0.0042 (9)
N20.0153 (10)0.0127 (11)0.0258 (12)0.0019 (8)0.0001 (8)0.0053 (9)
N30.0165 (10)0.0144 (11)0.0233 (12)0.0004 (8)0.0010 (9)0.0055 (9)
N40.0165 (10)0.0148 (11)0.0252 (12)0.0030 (8)0.0020 (8)0.0071 (9)
N50.0226 (11)0.0147 (11)0.0239 (12)0.0008 (8)0.0012 (9)0.0046 (9)
N60.061 (2)0.0298 (16)0.0298 (15)0.0082 (13)0.0065 (13)0.0028 (12)
C10.0390 (16)0.0170 (14)0.0266 (15)0.0045 (12)0.0081 (12)0.0056 (11)
C20.057 (2)0.0287 (17)0.0273 (17)0.0061 (15)0.0017 (15)0.0025 (13)
C30.057 (2)0.0283 (18)0.0386 (19)0.0165 (15)0.0202 (16)0.0078 (14)
C40.0342 (17)0.0337 (18)0.0365 (18)0.0016 (13)0.0130 (14)0.0067 (14)
C50.0193 (12)0.0150 (13)0.0244 (14)0.0006 (9)0.0034 (10)0.0035 (10)
C60.0172 (12)0.0149 (13)0.0268 (14)0.0004 (9)0.0025 (10)0.0049 (10)
C70.0157 (12)0.0163 (13)0.0199 (12)0.0010 (9)0.0036 (9)0.0067 (10)
C80.0159 (12)0.0129 (13)0.0236 (13)0.0027 (9)0.0006 (10)0.0062 (10)
C90.0180 (12)0.0161 (13)0.0242 (13)0.0014 (9)0.0006 (10)0.0081 (10)
C100.0192 (12)0.0191 (14)0.0205 (13)0.0045 (10)0.0011 (10)0.0043 (10)
C110.0248 (14)0.0165 (13)0.0284 (15)0.0043 (10)0.0026 (11)0.0061 (11)
C120.0293 (15)0.0255 (16)0.0305 (16)0.0043 (12)0.0065 (12)0.0112 (12)
C130.0322 (15)0.0335 (16)0.0245 (15)0.0112 (12)0.0064 (12)0.0060 (12)
C140.0417 (17)0.0222 (15)0.0234 (15)0.0094 (12)0.0021 (12)0.0007 (11)
C150.0302 (14)0.0195 (14)0.0254 (14)0.0024 (11)0.0016 (11)0.0065 (11)
C160.0184 (12)0.0101 (12)0.0238 (13)0.0048 (9)0.0001 (10)0.0066 (10)
C170.0190 (12)0.0158 (13)0.0223 (14)0.0017 (10)0.0018 (10)0.0037 (10)
C180.0177 (12)0.0178 (13)0.0175 (12)0.0041 (10)0.0025 (9)0.0049 (10)
C190.0180 (12)0.0164 (13)0.0244 (14)0.0018 (9)0.0007 (10)0.0083 (10)
C200.0182 (12)0.0250 (14)0.0264 (14)0.0017 (10)0.0014 (10)0.0117 (11)
C210.0233 (13)0.0216 (14)0.0259 (14)0.0000 (10)0.0024 (11)0.0104 (11)
C220.0218 (14)0.050 (2)0.0297 (16)0.0042 (13)0.0027 (12)0.0088 (14)
C230.0279 (16)0.055 (2)0.0291 (17)0.0064 (14)0.0003 (13)0.0042 (15)
C240.047 (2)0.0366 (18)0.0251 (16)0.0015 (14)0.0086 (14)0.0068 (13)
C250.0450 (19)0.042 (2)0.0292 (17)0.0185 (15)0.0087 (14)0.0105 (14)
C260.0302 (15)0.0353 (17)0.0268 (15)0.0101 (12)0.0007 (12)0.0113 (12)
C270.0174 (12)0.0167 (13)0.0292 (15)0.0043 (10)0.0031 (10)0.0057 (11)
C280.0191 (12)0.0186 (14)0.0250 (14)0.0018 (10)0.0015 (10)0.0056 (11)
C290.0261 (14)0.0157 (14)0.0289 (15)0.0017 (10)0.0017 (11)0.0026 (11)
C300.0323 (15)0.0256 (15)0.0261 (16)0.0008 (12)0.0004 (12)0.0091 (12)
C310.0401 (17)0.0238 (16)0.0268 (16)0.0068 (12)0.0026 (12)0.0025 (12)
C320.054 (2)0.0192 (15)0.0325 (17)0.0106 (13)0.0037 (14)0.0047 (12)
C330.0424 (17)0.0201 (15)0.0298 (16)0.0078 (12)0.0016 (13)0.0066 (12)
O1'0.0339 (11)0.0153 (10)0.0283 (11)0.0056 (8)0.0064 (8)0.0062 (8)
O2'0.0331 (11)0.0196 (11)0.0281 (11)0.0044 (8)0.0006 (8)0.0094 (8)
O3'0.0207 (9)0.0157 (9)0.0273 (10)0.0032 (7)0.0001 (7)0.0065 (7)
O4'0.0154 (8)0.0159 (9)0.0239 (9)0.0019 (7)0.0005 (7)0.0063 (7)
O5'0.0169 (9)0.0176 (9)0.0262 (10)0.0040 (7)0.0007 (7)0.0074 (7)
O6'0.0383 (12)0.0150 (10)0.0348 (12)0.0003 (8)0.0089 (9)0.0045 (8)
O7'0.085 (2)0.0523 (18)0.0302 (14)0.0145 (15)0.0223 (14)0.0055 (12)
O8'0.0685 (18)0.0356 (15)0.0390 (14)0.0180 (12)0.0072 (12)0.0075 (11)
N1'0.0207 (11)0.0120 (11)0.0272 (12)0.0001 (8)0.0001 (9)0.0059 (9)
N2'0.0147 (10)0.0143 (11)0.0259 (12)0.0015 (8)0.0016 (8)0.0048 (9)
N3'0.0168 (10)0.0153 (11)0.0229 (12)0.0002 (8)0.0011 (9)0.0050 (9)
N4'0.0161 (10)0.0133 (11)0.0224 (11)0.0026 (8)0.0004 (8)0.0045 (8)
N5'0.0240 (11)0.0133 (11)0.0197 (11)0.0024 (8)0.0015 (9)0.0029 (9)
N6'0.0387 (15)0.0374 (17)0.0283 (15)0.0069 (12)0.0072 (11)0.0023 (12)
C1'0.0374 (16)0.0172 (14)0.0250 (15)0.0050 (12)0.0082 (12)0.0047 (11)
C2'0.053 (2)0.0250 (17)0.0286 (16)0.0007 (14)0.0013 (14)0.0047 (13)
C3'0.0333 (16)0.0250 (16)0.0349 (17)0.0025 (12)0.0070 (13)0.0055 (13)
C4'0.054 (2)0.0224 (16)0.044 (2)0.0143 (14)0.0201 (16)0.0089 (14)
C5'0.0220 (13)0.0159 (14)0.0213 (13)0.0010 (10)0.0025 (10)0.0031 (10)
C6'0.0193 (12)0.0167 (13)0.0282 (15)0.0018 (10)0.0013 (10)0.0042 (11)
C7'0.0213 (13)0.0137 (13)0.0189 (12)0.0021 (10)0.0015 (10)0.0067 (10)
C8'0.0177 (12)0.0136 (13)0.0253 (14)0.0022 (10)0.0010 (10)0.0079 (10)
C9'0.0200 (12)0.0168 (13)0.0234 (14)0.0018 (10)0.0001 (10)0.0063 (10)
C10'0.0214 (13)0.0185 (14)0.0214 (13)0.0037 (10)0.0033 (10)0.0035 (11)
C11'0.0254 (14)0.0198 (14)0.0253 (14)0.0036 (10)0.0007 (11)0.0066 (11)
C12'0.0259 (14)0.0290 (16)0.0294 (15)0.0026 (11)0.0031 (11)0.0101 (12)
C13'0.0341 (16)0.0340 (17)0.0252 (15)0.0066 (13)0.0057 (12)0.0035 (12)
C14'0.0411 (17)0.0264 (16)0.0248 (15)0.0111 (13)0.0029 (13)0.0014 (12)
C15'0.0345 (15)0.0194 (14)0.0228 (14)0.0040 (11)0.0004 (11)0.0052 (11)
C16'0.0207 (13)0.0087 (12)0.0267 (14)0.0042 (9)0.0003 (10)0.0067 (10)
C17'0.0187 (12)0.0150 (13)0.0232 (13)0.0033 (9)0.0029 (10)0.0038 (10)
C18'0.0173 (12)0.0150 (12)0.0163 (12)0.0029 (9)0.0006 (9)0.0027 (9)
C19'0.0154 (12)0.0136 (12)0.0237 (13)0.0017 (9)0.0018 (10)0.0040 (10)
C20'0.0182 (12)0.0198 (13)0.0265 (14)0.0018 (10)0.0030 (10)0.0079 (10)
C21'0.0256 (13)0.0220 (14)0.0209 (13)0.0041 (10)0.0018 (10)0.0091 (11)
C22'0.0267 (14)0.0318 (16)0.0256 (15)0.0027 (12)0.0027 (11)0.0079 (12)
C23'0.0478 (19)0.0266 (16)0.0269 (16)0.0018 (14)0.0009 (13)0.0028 (12)
C24'0.054 (2)0.0323 (17)0.0240 (16)0.0172 (15)0.0072 (14)0.0075 (12)
C25'0.0338 (16)0.0453 (19)0.0281 (16)0.0170 (14)0.0051 (12)0.0100 (13)
C26'0.0253 (14)0.0331 (16)0.0253 (14)0.0056 (12)0.0021 (11)0.0091 (12)
C27'0.0179 (13)0.0163 (14)0.0263 (14)0.0023 (10)0.0003 (10)0.0048 (10)
C28'0.0178 (12)0.0205 (14)0.0225 (14)0.0027 (10)0.0016 (10)0.0031 (11)
C29'0.0233 (13)0.0212 (14)0.0251 (14)0.0006 (10)0.0013 (11)0.0067 (11)
C30'0.0298 (14)0.0222 (15)0.0242 (15)0.0004 (11)0.0010 (11)0.0031 (12)
C31'0.0305 (15)0.0285 (16)0.0205 (14)0.0029 (12)0.0022 (11)0.0011 (12)
C32'0.0398 (17)0.0219 (15)0.0311 (16)0.0109 (12)0.0031 (13)0.0001 (12)
C33'0.0342 (15)0.0235 (15)0.0268 (15)0.0103 (11)0.0041 (12)0.0065 (11)
Geometric parameters (Å, º) top
O1—C51.356 (3)O1'—C5'1.349 (3)
O1—C11.476 (4)O1'—C1'1.477 (4)
O2—C51.218 (4)O2'—C5'1.220 (3)
O3—C71.227 (3)O3'—C7'1.222 (3)
O4—C161.246 (3)O4'—C16'1.246 (3)
O5—C181.224 (3)O5'—C18'1.225 (3)
O6—C271.217 (3)O6'—C27'1.206 (3)
O7—N61.227 (4)O7'—N6'1.221 (4)
O8—N61.217 (4)O8'—N6'1.229 (4)
N1—C51.340 (4)N1'—C5'1.355 (4)
N1—C61.447 (3)N1'—C6'1.448 (3)
N1—H1A0.9000N1'—H1'A0.9000
N2—C71.348 (4)N2'—C7'1.353 (3)
N2—C81.421 (3)N2'—C8'1.413 (3)
N2—H2D0.9000N2'—H2'D0.9000
N3—C161.334 (4)N3'—C16'1.331 (4)
N3—C171.456 (3)N3'—C17'1.456 (3)
N3—H3D0.9000N3'—H3'D0.9000
N4—C181.337 (3)N4'—C18'1.343 (3)
N4—C191.454 (3)N4'—C19'1.454 (3)
N4—H4D0.9000N4'—H4'D0.9000
N5—C271.364 (4)N5'—C27'1.370 (4)
N5—C281.416 (4)N5'—C28'1.410 (4)
N5—H5A0.9000N5'—H5'A0.9000
N6—C311.470 (4)N6'—C31'1.466 (4)
C1—C21.508 (5)C1'—C2'1.509 (5)
C1—C41.518 (4)C1'—C4'1.520 (4)
C1—C31.524 (4)C1'—C3'1.519 (4)
C2—H2A0.9600C2'—H2'A0.9600
C2—H2B0.9600C2'—H2'B0.9599
C2—H2C0.9600C2'—H2'C0.9600
C3—H3A0.9600C3'—H3'A0.9600
C3—H3B0.9599C3'—H3'B0.9600
C3—H3C0.9600C3'—H3'C0.9600
C4—H4A0.9600C4'—H4'A0.9600
C4—H4B0.9600C4'—H4'B0.9600
C4—H4C0.9600C4'—H4'C0.9600
C6—C71.523 (3)C6'—C7'1.530 (4)
C6—H6A0.9600C6'—H6'A0.9600
C6—H6B0.9601C6'—H6'B0.9600
C8—C91.339 (4)C8'—C9'1.339 (4)
C8—C161.489 (4)C8'—C16'1.488 (4)
C9—C101.470 (4)C9'—C10'1.463 (4)
C9—H9A0.9600C9'—H9'A0.9600
C10—C111.393 (4)C10'—C11'1.390 (4)
C10—C151.399 (4)C10'—C15'1.398 (4)
C11—C121.387 (4)C11'—C12'1.390 (4)
C11—H11A0.9600C11'—H11B0.9600
C12—C131.393 (4)C12'—C13'1.385 (5)
C12—H12A0.9600C12'—H12B0.9600
C13—C141.381 (5)C13'—C14'1.379 (5)
C13—H13A0.9600C13'—H13B0.9600
C14—C151.390 (4)C14'—C15'1.391 (4)
C14—H14A0.9600C14'—H14B0.9600
C15—H15A0.9601C15'—H15B0.9600
C17—C181.521 (4)C17'—C18'1.522 (4)
C17—H17A0.9600C17'—H17C0.9600
C17—H17B0.9600C17'—H17D0.9600
C19—C201.529 (4)C19'—C20'1.531 (4)
C19—C271.537 (4)C19'—C27'1.543 (4)
C19—H19A0.9600C19'—H19B0.9600
C20—C211.518 (4)C20'—C21'1.517 (4)
C20—H20A0.9600C20'—H20C0.9600
C20—H20B0.9600C20'—H20D0.9600
C21—C221.380 (4)C21'—C26'1.386 (4)
C21—C261.393 (4)C21'—C22'1.388 (4)
C22—C231.390 (5)C22'—C23'1.392 (4)
C22—H22A0.9599C22'—H22B0.9600
C23—C241.375 (5)C23'—C24'1.373 (5)
C23—H23A0.9600C23'—H23B0.9600
C24—C251.380 (5)C24'—C25'1.383 (5)
C24—H24A0.9600C24'—H24B0.9600
C25—C261.382 (4)C25'—C26'1.396 (4)
C25—H25A0.9599C25'—H25B0.9600
C26—H26A0.9600C26'—H26B0.9600
C28—C331.388 (4)C28'—C29'1.391 (4)
C28—C291.391 (4)C28'—C33'1.393 (4)
C29—C301.382 (4)C29'—C30'1.382 (4)
C29—H29A0.9600C29'—H29B0.9600
C30—C311.380 (5)C30'—C31'1.380 (5)
C30—H30A0.9599C30'—H30B0.9601
C31—C321.368 (5)C31'—C32'1.380 (5)
C32—C331.397 (5)C32'—C33'1.393 (4)
C32—H32A0.9600C32'—H32B0.9600
C33—H33A0.9600C33'—H33B0.9599
C5—O1—C1120.1 (2)C5'—O1'—C1'120.1 (2)
C5—N1—C6117.8 (2)C5'—N1'—C6'116.8 (2)
C5—N1—H1A121.2C5'—N1'—H1'A121.6
C6—N1—H1A121.0C6'—N1'—H1'A121.7
C7—N2—C8120.8 (2)C7'—N2'—C8'122.2 (2)
C7—N2—H2D119.6C7'—N2'—H2'D118.9
C8—N2—H2D119.6C8'—N2'—H2'D118.8
C16—N3—C17118.6 (2)C16'—N3'—C17'118.7 (2)
C16—N3—H3D120.8C16'—N3'—H3'D120.7
C17—N3—H3D120.6C17'—N3'—H3'D120.6
C18—N4—C19119.5 (2)C18'—N4'—C19'123.3 (2)
C18—N4—H4D120.3C18'—N4'—H4'D118.4
C19—N4—H4D120.2C19'—N4'—H4'D118.4
C27—N5—C28127.6 (2)C27'—N5'—C28'127.6 (2)
C27—N5—H5A116.1C27'—N5'—H5'A116.2
C28—N5—H5A116.3C28'—N5'—H5'A116.1
O8—N6—O7123.2 (3)O7'—N6'—O8'123.6 (3)
O8—N6—C31118.6 (3)O7'—N6'—C31'118.5 (3)
O7—N6—C31118.2 (3)O8'—N6'—C31'117.8 (3)
O1—C1—C2109.3 (3)O1'—C1'—C2'109.1 (3)
O1—C1—C4111.0 (2)O1'—C1'—C4'102.7 (2)
C2—C1—C4113.9 (3)C2'—C1'—C4'111.0 (3)
O1—C1—C3102.5 (2)O1'—C1'—C3'110.6 (2)
C2—C1—C3109.8 (3)C2'—C1'—C3'113.2 (3)
C4—C1—C3109.8 (3)C4'—C1'—C3'109.6 (3)
C1—C2—H2A109.7C1'—C2'—H2'A109.4
C1—C2—H2B109.4C1'—C2'—H2'B109.7
H2A—C2—H2B109.5H2'A—C2'—H2'B109.5
C1—C2—H2C109.3C1'—C2'—H2'C109.4
H2A—C2—H2C109.5H2'A—C2'—H2'C109.5
H2B—C2—H2C109.5H2'B—C2'—H2'C109.5
C1—C3—H3A109.7C1'—C3'—H3'A109.6
C1—C3—H3B109.4C1'—C3'—H3'B109.5
H3A—C3—H3B109.5H3'A—C3'—H3'B109.5
C1—C3—H3C109.3C1'—C3'—H3'C109.3
H3A—C3—H3C109.5H3'A—C3'—H3'C109.5
H3B—C3—H3C109.5H3'B—C3'—H3'C109.5
C1—C4—H4A109.1C1'—C4'—H4'A109.4
C1—C4—H4B109.5C1'—C4'—H4'B109.4
H4A—C4—H4B109.5H4'A—C4'—H4'B109.5
C1—C4—H4C109.7C1'—C4'—H4'C109.6
H4A—C4—H4C109.5H4'A—C4'—H4'C109.5
H4B—C4—H4C109.5H4'B—C4'—H4'C109.5
O2—C5—N1124.2 (3)O2'—C5'—O1'126.1 (3)
O2—C5—O1125.2 (3)O2'—C5'—N1'123.5 (3)
N1—C5—O1110.6 (2)O1'—C5'—N1'110.5 (2)
N1—C6—C7109.6 (2)N1'—C6'—C7'109.0 (2)
N1—C6—H6A109.9N1'—C6'—H6'A109.8
C7—C6—H6A109.7C7'—C6'—H6'A109.9
N1—C6—H6B109.6N1'—C6'—H6'B110.0
C7—C6—H6B109.7C7'—C6'—H6'B109.9
H6A—C6—H6B108.2H6'A—C6'—H6'B108.3
O3—C7—N2122.4 (2)O3'—C7'—N2'122.1 (2)
O3—C7—C6122.3 (2)O3'—C7'—C6'122.1 (2)
N2—C7—C6115.3 (2)N2'—C7'—C6'115.8 (2)
C9—C8—N2124.1 (2)C9'—C8'—N2'124.3 (2)
C9—C8—C16118.1 (2)C9'—C8'—C16'117.5 (2)
N2—C8—C16117.6 (2)N2'—C8'—C16'117.8 (2)
C8—C9—C10128.9 (2)C8'—C9'—C10'130.2 (2)
C8—C9—H9A115.5C8'—C9'—H9'A114.9
C10—C9—H9A115.5C10'—C9'—H9'A114.9
C11—C10—C15118.4 (3)C11'—C10'—C15'118.2 (3)
C11—C10—C9123.8 (2)C11'—C10'—C9'123.6 (2)
C15—C10—C9117.7 (2)C15'—C10'—C9'118.1 (3)
C12—C11—C10120.5 (3)C10'—C11'—C12'120.9 (3)
C12—C11—H11A119.8C10'—C11'—H11B119.6
C10—C11—H11A119.7C12'—C11'—H11B119.5
C11—C12—C13120.8 (3)C13'—C12'—C11'120.2 (3)
C11—C12—H12A119.6C13'—C12'—H12B119.7
C13—C12—H12A119.6C11'—C12'—H12B120.0
C14—C13—C12118.9 (3)C14'—C13'—C12'119.6 (3)
C14—C13—H13A120.6C14'—C13'—H13B120.2
C12—C13—H13A120.5C12'—C13'—H13B120.2
C13—C14—C15120.7 (3)C13'—C14'—C15'120.3 (3)
C13—C14—H14A119.7C13'—C14'—H14B119.8
C15—C14—H14A119.6C15'—C14'—H14B120.0
C14—C15—C10120.6 (3)C14'—C15'—C10'120.7 (3)
C14—C15—H15A119.7C14'—C15'—H15B119.6
C10—C15—H15A119.6C10'—C15'—H15B119.7
O4—C16—N3120.1 (2)O4'—C16'—N3'120.5 (2)
O4—C16—C8120.1 (2)O4'—C16'—C8'120.5 (2)
N3—C16—C8119.7 (2)N3'—C16'—C8'118.9 (2)
N3—C17—C18110.0 (2)N3'—C17'—C18'109.6 (2)
N3—C17—H17A109.5N3'—C17'—H17C109.9
C18—C17—H17A109.6C18'—C17'—H17C109.7
N3—C17—H17B109.8N3'—C17'—H17D109.5
C18—C17—H17B109.7C18'—C17'—H17D109.8
H17A—C17—H17B108.2H17C—C17'—H17D108.2
O5—C18—N4121.2 (2)O5'—C18'—N4'122.7 (2)
O5—C18—C17121.1 (2)O5'—C18'—C17'121.8 (2)
N4—C18—C17117.7 (2)N4'—C18'—C17'115.4 (2)
N4—C19—C20111.1 (2)N4'—C19'—C20'112.5 (2)
N4—C19—C27113.0 (2)N4'—C19'—C27'113.4 (2)
C20—C19—C27112.3 (2)C20'—C19'—C27'112.1 (2)
N4—C19—H19A106.7N4'—C19'—H19B106.0
C20—C19—H19A106.7C20'—C19'—H19B106.1
C27—C19—H19A106.6C27'—C19'—H19B106.1
C21—C20—C19113.8 (2)C21'—C20'—C19'110.9 (2)
C21—C20—H20A108.8C21'—C20'—H20C109.5
C19—C20—H20A108.7C19'—C20'—H20C109.5
C21—C20—H20B108.8C21'—C20'—H20D109.4
C19—C20—H20B108.8C19'—C20'—H20D109.4
H20A—C20—H20B107.7H20C—C20'—H20D108.1
C22—C21—C26117.7 (3)C26'—C21'—C22'118.5 (3)
C22—C21—C20123.2 (3)C26'—C21'—C20'121.2 (3)
C26—C21—C20119.0 (3)C22'—C21'—C20'120.1 (2)
C21—C22—C23120.7 (3)C21'—C22'—C23'120.7 (3)
C21—C22—H22A119.7C21'—C22'—H22B119.7
C23—C22—H22A119.7C23'—C22'—H22B119.6
C24—C23—C22120.7 (3)C24'—C23'—C22'120.3 (3)
C24—C23—H23A119.7C24'—C23'—H23B119.8
C22—C23—H23A119.6C22'—C23'—H23B119.9
C23—C24—C25119.5 (3)C23'—C24'—C25'119.8 (3)
C23—C24—H24A120.3C23'—C24'—H24B120.3
C25—C24—H24A120.2C25'—C24'—H24B120.0
C24—C25—C26119.5 (3)C24'—C25'—C26'119.9 (3)
C24—C25—H25A120.4C24'—C25'—H25B120.1
C26—C25—H25A120.2C26'—C25'—H25B120.0
C25—C26—C21121.8 (3)C21'—C26'—C25'120.7 (3)
C25—C26—H26A119.1C21'—C26'—H26B119.8
C21—C26—H26A119.0C25'—C26'—H26B119.5
O6—C27—N5123.8 (3)O6'—C27'—N5'124.5 (3)
O6—C27—C19120.5 (3)O6'—C27'—C19'120.4 (3)
N5—C27—C19115.7 (2)N5'—C27'—C19'114.8 (2)
C33—C28—C29120.1 (3)C29'—C28'—C33'120.3 (3)
C33—C28—N5122.1 (3)C29'—C28'—N5'117.2 (2)
C29—C28—N5117.7 (2)C33'—C28'—N5'122.5 (3)
C30—C29—C28120.7 (3)C30'—C29'—C28'120.8 (3)
C30—C29—H29A119.6C30'—C29'—H29B119.7
C28—C29—H29A119.7C28'—C29'—H29B119.5
C31—C30—C29118.5 (3)C31'—C30'—C29'118.4 (3)
C31—C30—H30A120.8C31'—C30'—H30B120.8
C29—C30—H30A120.7C29'—C30'—H30B120.8
C32—C31—C30121.9 (3)C32'—C31'—C30'122.0 (3)
C32—C31—N6119.4 (3)C32'—C31'—N6'119.5 (3)
C30—C31—N6118.6 (3)C30'—C31'—N6'118.5 (3)
C31—C32—C33119.7 (3)C31'—C32'—C33'119.6 (3)
C31—C32—H32A120.2C31'—C32'—H32B120.1
C33—C32—H32A120.1C33'—C32'—H32B120.2
C28—C33—C32119.1 (3)C32'—C33'—C28'118.9 (3)
C28—C33—H33A120.4C32'—C33'—H33B120.4
C32—C33—H33A120.5C28'—C33'—H33B120.7
C5—O1—C1—C269.0 (3)C5'—O1'—C1'—C2'70.8 (3)
C5—O1—C1—C457.4 (4)C5'—O1'—C1'—C4'171.3 (3)
C5—O1—C1—C3174.5 (3)C5'—O1'—C1'—C3'54.4 (4)
C6—N1—C5—O210.3 (4)C1'—O1'—C5'—O2'3.2 (4)
C6—N1—C5—O1169.8 (2)C1'—O1'—C5'—N1'176.1 (2)
C1—O1—C5—O20.8 (4)C6'—N1'—C5'—O2'15.4 (4)
C1—O1—C5—N1179.1 (2)C6'—N1'—C5'—O1'164.0 (2)
C5—N1—C6—C753.9 (3)C5'—N1'—C6'—C7'52.7 (3)
C8—N2—C7—O31.3 (4)C8'—N2'—C7'—O3'0.7 (4)
C8—N2—C7—C6177.4 (2)C8'—N2'—C7'—C6'178.3 (2)
N1—C6—C7—O335.0 (4)N1'—C6'—C7'—O3'29.7 (4)
N1—C6—C7—N2143.8 (2)N1'—C6'—C7'—N2'149.3 (2)
C7—N2—C8—C9126.8 (3)C7'—N2'—C8'—C9'137.9 (3)
C7—N2—C8—C1659.3 (3)C7'—N2'—C8'—C16'49.9 (3)
N2—C8—C9—C107.6 (5)N2'—C8'—C9'—C10'9.2 (5)
C16—C8—C9—C10178.5 (2)C16'—C8'—C9'—C10'178.6 (3)
C8—C9—C10—C1127.8 (5)C8'—C9'—C10'—C11'29.5 (5)
C8—C9—C10—C15155.1 (3)C8'—C9'—C10'—C15'154.2 (3)
C15—C10—C11—C120.8 (4)C15'—C10'—C11'—C12'1.0 (4)
C9—C10—C11—C12176.3 (3)C9'—C10'—C11'—C12'175.3 (3)
C10—C11—C12—C132.0 (5)C10'—C11'—C12'—C13'1.8 (5)
C11—C12—C13—C141.0 (5)C11'—C12'—C13'—C14'0.2 (5)
C12—C13—C14—C151.3 (5)C12'—C13'—C14'—C15'2.1 (5)
C13—C14—C15—C102.5 (5)C13'—C14'—C15'—C10'2.8 (5)
C11—C10—C15—C141.5 (4)C11'—C10'—C15'—C14'1.2 (4)
C9—C10—C15—C14178.7 (3)C9'—C10'—C15'—C14'177.8 (3)
C17—N3—C16—O40.9 (4)C17'—N3'—C16'—O4'0.6 (4)
C17—N3—C16—C8178.0 (2)C17'—N3'—C16'—C8'175.6 (2)
C9—C8—C16—O422.0 (4)C9'—C8'—C16'—O4'31.3 (4)
N2—C8—C16—O4163.7 (2)N2'—C8'—C16'—O4'156.0 (2)
C9—C8—C16—N3155.2 (3)C9'—C8'—C16'—N3'143.7 (3)
N2—C8—C16—N319.2 (3)N2'—C8'—C16'—N3'29.0 (3)
C16—N3—C17—C1855.1 (3)C16'—N3'—C17'—C18'55.5 (3)
C19—N4—C18—O52.8 (4)C19'—N4'—C18'—O5'6.1 (4)
C19—N4—C18—C17175.9 (2)C19'—N4'—C18'—C17'173.9 (2)
N3—C17—C18—O546.3 (3)N3'—C17'—C18'—O5'49.9 (3)
N3—C17—C18—N4135.0 (2)N3'—C17'—C18'—N4'130.1 (2)
C18—N4—C19—C20141.4 (2)C18'—N4'—C19'—C20'67.0 (3)
C18—N4—C19—C2791.3 (3)C18'—N4'—C19'—C27'61.4 (3)
N4—C19—C20—C2147.5 (3)N4'—C19'—C20'—C21'53.9 (3)
C27—C19—C20—C21175.2 (2)C27'—C19'—C20'—C21'177.0 (2)
C19—C20—C21—C2235.2 (4)C19'—C20'—C21'—C26'89.0 (3)
C19—C20—C21—C26142.3 (3)C19'—C20'—C21'—C22'87.0 (3)
C26—C21—C22—C231.8 (5)C26'—C21'—C22'—C23'1.5 (5)
C20—C21—C22—C23175.7 (3)C20'—C21'—C22'—C23'174.6 (3)
C21—C22—C23—C240.1 (6)C21'—C22'—C23'—C24'1.1 (5)
C22—C23—C24—C251.9 (6)C22'—C23'—C24'—C25'0.4 (5)
C23—C24—C25—C261.8 (5)C23'—C24'—C25'—C26'1.3 (5)
C24—C25—C26—C210.2 (5)C22'—C21'—C26'—C25'0.6 (5)
C22—C21—C26—C252.0 (5)C20'—C21'—C26'—C25'175.5 (3)
C20—C21—C26—C25175.6 (3)C24'—C25'—C26'—C21'0.8 (5)
C28—N5—C27—O69.2 (5)C28'—N5'—C27'—O6'0.1 (5)
C28—N5—C27—C19168.2 (2)C28'—N5'—C27'—C19'175.0 (2)
N4—C19—C27—O6165.7 (2)N4'—C19'—C27'—O6'164.2 (3)
C20—C19—C27—O639.1 (3)C20'—C19'—C27'—O6'35.5 (3)
N4—C19—C27—N516.8 (3)N4'—C19'—C27'—N5'20.7 (3)
C20—C19—C27—N5143.4 (2)C20'—C19'—C27'—N5'149.3 (2)
C27—N5—C28—C3323.1 (4)C27'—N5'—C28'—C29'157.5 (3)
C27—N5—C28—C29160.2 (3)C27'—N5'—C28'—C33'23.2 (4)
C33—C28—C29—C300.2 (4)C33'—C28'—C29'—C30'0.4 (4)
N5—C28—C29—C30176.6 (3)N5'—C28'—C29'—C30'179.7 (3)
C28—C29—C30—C310.3 (4)C28'—C29'—C30'—C31'0.2 (4)
C29—C30—C31—C321.3 (5)C29'—C30'—C31'—C32'0.7 (5)
C29—C30—C31—N6178.6 (3)C29'—C30'—C31'—N6'180.0 (3)
O8—N6—C31—C322.4 (5)O7'—N6'—C31'—C32'176.2 (3)
O7—N6—C31—C32177.5 (4)O8'—N6'—C31'—C32'3.2 (5)
O8—N6—C31—C30177.7 (4)O7'—N6'—C31'—C30'3.1 (5)
O7—N6—C31—C302.4 (5)O8'—N6'—C31'—C30'177.5 (3)
C30—C31—C32—C331.7 (5)C30'—C31'—C32'—C33'0.5 (5)
N6—C31—C32—C33178.2 (3)N6'—C31'—C32'—C33'179.8 (3)
C29—C28—C33—C320.1 (5)C31'—C32'—C33'—C28'0.2 (5)
N5—C28—C33—C32176.8 (3)C29'—C28'—C33'—C32'0.6 (4)
C31—C32—C33—C281.0 (5)N5'—C28'—C33'—C32'179.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O3i0.902.062.898 (3)154
N2—H2D···O5ii0.902.042.879 (3)156
N3—H3D···O20.902.273.053 (3)145
N4—H4D···O4iii0.902.062.917 (3)160
N5—H5A···O40.902.092.917 (3)153
N5—H5A···N40.902.262.724 (3)112
N1—H1A···O3iv0.902.162.965 (3)149
N2—H2D···O5v0.901.832.693 (3)159
N3—H3D···O20.902.463.215 (3)141
N4—H4D···O4vi0.902.052.873 (3)151
N5—H5A···O40.902.132.964 (3)153
N5—H5A···N40.902.282.737 (3)111
Symmetry codes: (i) x, y, z+1; (ii) x, y1, z+1; (iii) x+1, y1, z+1; (iv) x, y, z1; (v) x, y+1, z1; (vi) x1, y+1, z1.

Experimental details

Crystal data
Chemical formulaC33H36N6O8
Mr644.68
Crystal system, space groupTriclinic, P1
Temperature (K)105
a, b, c (Å)10.328 (2), 11.605 (2), 14.796 (3)
α, β, γ (°)70.00 (3), 86.37 (3), 76.19 (3)
V3)1617.9 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.5 × 0.4 × 0.3
Data collection
DiffractometerKUMA KM–4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
11299, 5804, 5429
Rint0.029
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.105, 1.02
No. of reflections5804
No. of parameters847
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.37
Absolute structureFlack (1983)

Computer programs: KUMA Diffraction Software (KUMA, 1998), KUMA Diffraction Software, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 199b), SHELXTL (Sheldrick, 1990), SHELXL97.

Selected geometric parameters (Å, º) top
N2—C81.421 (3)N2'—C8'1.413 (3)
N4—C191.454 (3)N4'—C19'1.454 (3)
C8—C91.339 (4)C8'—C9'1.339 (4)
C8—C161.489 (4)C8'—C16'1.488 (4)
C19—C201.529 (4)C19'—C20'1.531 (4)
C19—C271.537 (4)C19'—C27'1.543 (4)
C9—C8—N2124.1 (2)C9'—C8'—N2'124.3 (2)
C9—C8—C16118.1 (2)C9'—C8'—C16'117.5 (2)
N2—C8—C16117.6 (2)N2'—C8'—C16'117.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O3'i0.902.062.898 (3)154.4
N2—H2D···O5'ii0.902.042.879 (3)155.5
N3—H3D···O20.902.273.053 (3)145.2
N4—H4D···O4'iii0.902.062.917 (3)159.5
N5—H5A···O40.902.092.917 (3)152.8
N5—H5A···N40.902.262.724 (3)111.6
N1'—H1'A···O3iv0.902.162.965 (3)149.2
N2'—H2'D···O5v0.901.832.693 (3)158.9
N3'—H3'D···O2'0.902.463.215 (3)141.1
N4'—H4'D···O4vi0.902.052.873 (3)151.3
N5'—H5'A···O4'0.902.132.964 (3)153.2
N5'—H5'A···N4'0.902.282.737 (3)111.2
Symmetry codes: (i) x, y, z+1; (ii) x, y1, z+1; (iii) x+1, y1, z+1; (iv) x, y, z1; (v) x, y+1, z1; (vi) x1, y+1, z1.
Important torsional angles. top
AngleAB
Φ0 C6-N1-C5-O1-169.8 (2)164.0 (2)
ω0 C1-O1-C5-N1-179.1 (2)-176.1 (2)
Φ1 C5-N1-C6-C753.9 (3)-52.7 (3)
ω1 C8-N2-C7-C6177.4 (2)-178.3 (2)
Ψ1 N1-C6-C7-N2-143.8 (2)149.3 (2)
Φ2 C7-N2-C8-C16-59.3 (3)49.9 (3)
χ1 N2-C8-C9-C10-7.6 (4)9.2 (5)
χ2,1 C8-C9-C10-C11-27.8 (4)29.5 (5)
χ2,2 C8-C9-C10-C15155.1 (2)-154.2 (3)
ω2 C17-N3-C16-C8-178.0 (2)175.3 (3)
Ψ2 N2-C8-C16-N3-19.2 (3)29.0 (3)
Φ3 C16-N3-C17-C1855.1 (2)-55.6 (3)
ω3 C19-N4-C18-C17-175.9 (2)173.9 (2)
Ψ3 N3-C17-C18-N4-135.0 (2)130.1 (2)
Φ4 C18-N4-C19-C27-91.3 (2)61.4 (3)
ω4 C28-N5-C27-C19168.2 (2)175.0 (2)
Ψ4 N4-C19-C27-N516.8 (3)20.7 (3)
 

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