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The title peptide, C7H14N2O3, crystallizes with seven independent mol­ecules in the asymmetric unit. All have essentially the same overall conformation, but some flexibility is exhibited by the glycine residue. It appears that the high Z' value, observed only three times before for an organic compound, permits formation of shorter hydrogen bonds in one of the two head-to-tail chains involving the N-terminal amino groups and the C-terminal carboxyl­ate groups than found in a hypothetical model structure of glycyl-L-valine with Z' = 1, and that it furthermore alleviates strain associated with an eclipsed orientation of the amino group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106052474/jz3047sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106052474/jz3047Isup2.hkl
Contains datablock I

CCDC reference: 634906

Comment top

Among dipeptides constructed from the 20 natural amino acids, the Gly–Xaa series of crystal structures, where Xaa is any amino acid, is the most complete for a specific N-terminal amino acid, with 13 entries in the Cambridge Structural Database (CSD, Version 5.27 of November 2005; Allen, 2002). In a student project, we sought to expand this group of structures towards completeness by crystallization of the title compound, Gly-L-Val, (I).

Thin flakes of (I) obtained by slow evaporation were generally of low quality, but a specimen usable for data collection was found after a number of tests. The initial observation of a 44 Å unit-cell axis indicated that this was an unusual dipeptide crystal, a suspicion that was subsequently verified when structure determination revealed seven independent peptide molecules in the asymmetric unit, labelled A to G (Fig. 1). All seven molecules have essentially the same conformation, but with some torsion angle variations, in particular for rotation about the C1—C2 bond (ψ1) (Table 1 and Fig. 2). It is interesting to note that the main chain conformation of Gly-L-Leu [(II); Pattabhi et al., 1974] can be seen to represent an average of the seven Gly-L-Val conformations (Table 1), and the closely related monoclinic structure of (II) provides some clues as to why (I) has crystallized with Z' = 7.

As seen for (II), the crystal structure of (I) is divided into hydrophobic and hydrophilic layers (Fig. 3), and we first suspected that the side-chain modification going from Leu to Val rendered efficient packing of the side chain difficult with Z' limited to 1. To test this hypothesis, a molecular modelling program (SYBYL; Tripos, 2005) was used to construct a theoretical Gly-L-Val structure with Z' = 1, based on (II) but adapted to the correct space group, P212121. This model showed no unfavourable short contacts or large voids compared with the structure of (I).

Our attention then turned to the hydrogen-bonding pattern, with contacts listed in Table 2. Atoms H1 and H3 are involved in head-to-tail chains within a hydrophilic sheet that also comprises the N2—H4···O3 interactions. Two such antiparallel sheets are interconnected by N1—H2···O3 hydrogen bonds and thus generate a hydrophilic layer (Fig. 3). A peculiarity of (II) is the eclipsed conformation of the amino group, as reflected by the H3—N1—C1—C2 torsion angle in Table 1, which is required to minimize the H···O distance in the N1—H3···O2 interaction (Table 2). In (I), two different rotational modes are observed for the amino group, one with H3—N1—C1—C2 < 0° for molecules B, C, E and F, and one with H3—N1—C1—C2 > 0° for molecules A, D and G. The fully eclipsed conformation is thus avoided, and at the same time the associated hydrogen bonds are significantly shorter overall than in (II) (while hydrogen bonds involving atoms H1 and H2 are unchanged).

A further effect of this rearrangement can be seen as a reduction of the structural periodicity along the head-to-tail chains from 6.369 Å for (II) (a axis) to 6.299 Å for (I) (c axis/7). On the other hand, the shorter N2—H4···O3 hydrogen bond in (I) compared with (II) is most probably attributable mainly to more efficient packing of Val than Leu side chains, indicated by a shorter cell axis [5.5238 (7) Å for (I) and 5.565 Å for (II)], as only molecules of the same kind (A···A etc.) are involved.

The monclinic C2 structure of L-Ala-L-Leu hemihydrate (Görbitz, 1999) is related to both (I) and (II) (Fig. 3), with essentially the same molecular conformation. Space for the extra methyl side chain at residue I is nicely provided by insertion of extra water molecules in the hydrophilic layers. Water thus replaces atom O3 as the acceptor in the N1—H2···O3 interaction, and at the same time the two hydrogen-bonded sheets in a single layer (see above) switch from antiparallel to parallel orientation to provide carboxylate acceptors for both water H atoms.

There are only three other structures in the CSD with Z' = 7. Two of these are peptides, viz. L-Met-L-Ala in space group P61 (Görbitz, 2003) and Boc-L-Phe-L-Leu-OBzl, a protected dipeptide fragment of enkephalin, in space group P21 (Antolić et al., 1999). In both cases, the seven molecules exhibit a mixture of conformations, particularly with regard to the side chains, but also with extensive flexibility for the peptide main chains. The third compound, 2-cyano-2-isonitroso-N-morpholinylacetamide [(III); Eddings et al., 2004], shares the P212121 space group with (I) and, with its 7.3 × 14.4 × 54.8 Å unit cell, shows some of the same packing features, but not the division into hydrophobic and hydrophilic layers as seen for (I). In (III), there is a 4:3 distribution between two different chair conformations for the six-membered ring.

Experimental top

The title peptide was obtained from Bachem. Crystals in the shape of extremely thin plates were obtained by slow evaporation of an aqueous solution.

Refinement top

H atoms were positioned with idealized geometry, with amide H atoms in the peptide plane, and fixed C—H and N—H distances of 0.98–1.00 Å and 0.88–0.91 Å, respectively. [Please check added text] Rigid rotation was permitted for amino groups only. Uiso(H) values were 1.2Ueq of the carrier atom, or 1.5Ueq(parent) for amino and methyl groups. In the absence of significant anomalous scattering effects, 4887 Friedel pairs were merged. The absolute configuration was known for the purchased material.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I). Displacement ellipsoids are drawn at the 50% probability level. Atomic numbering is shown for molecule A only. The valyl side chain is shaded differently for molecules A, B, C, D, E, F and G.
[Figure 2] Fig. 2. Overlap diagram of the seven molecules in the asymmetric unit of (I) after best fit to the average structure (not shown).
[Figure 3] Fig. 3. (a) The molecular packing and unit cell of (I), viewed along the a axis. Hydrogen bonds are indicated by dashed lines. H atoms not involved in such interactions have been omitted for clarity. One half of the molecules are shown in a space-filling representation. The shading is similar to that in Fig. 1. (b) The crystal structure of Gly-L-Leu (Pattabhi et al., 1974), viewed along the b axis. (c) The crystal structure of L-Ala-L-Leu (Görbitz, 1999), viewed along the c axis.
glycyl-L-valine top
Crystal data top
C7H14N2O3Dx = 1.251 Mg m3
Mr = 174.20Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 4643 reflections
a = 5.5238 (7) Åθ = 0.9–25.0°
b = 26.581 (3) ŵ = 0.10 mm1
c = 44.093 (5) ÅT = 105 K
V = 6474.0 (14) Å3Plate, colourless
Z = 280.75 × 0.25 × 0.01 mm
F(000) = 2632
Data collection top
Siemens SMART CCD area-detector
diffractometer
4122 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.125
Graphite monochromatorθmax = 25.0°, θmin = 0.9°
Detector resolution: 8.3 pixels mm-1h = 66
ω scansk = 3131
35141 measured reflectionsl = 5239
6579 independent 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)] = 0.073H-atom parameters constrained
wR(F2) = 0.172 w = 1/[σ2(Fo2) + (0.048P)2 + 2.98P]
where P = (Fo2 + 2Fc2)/3
S = 1.28(Δ/σ)max = 0.009
6579 reflectionsΔρmax = 0.34 e Å3
765 parametersΔρmin = 0.35 e Å3
1101 restraintsExtinction correction: SHELXTL (Bruker, 2000), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00086 (13)
Crystal data top
C7H14N2O3V = 6474.0 (14) Å3
Mr = 174.20Z = 28
Orthorhombic, P212121Mo Kα radiation
a = 5.5238 (7) ŵ = 0.10 mm1
b = 26.581 (3) ÅT = 105 K
c = 44.093 (5) Å0.75 × 0.25 × 0.01 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
4122 reflections with I > 2σ(I)
35141 measured reflectionsRint = 0.125
6579 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0731101 restraints
wR(F2) = 0.172H-atom parameters constrained
S = 1.28Δρmax = 0.34 e Å3
6579 reflectionsΔρmin = 0.35 e Å3
765 parameters
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. Data were collected by measuring three sets of exposures with the detector set at 2θ = 29°, crystal-to-detector distance 5.00 cm. Refinement of F2 against ALL reflections.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.6208 (7)0.69919 (15)0.09435 (9)0.0254 (11)
O2A0.6337 (8)0.70171 (15)0.01811 (10)0.0335 (12)
O3A0.9653 (7)0.65673 (17)0.02741 (10)0.0329 (12)
N1A0.2233 (9)0.73321 (17)0.12486 (9)0.0190 (12)
H1A0.12150.71510.13690.029*
H2A0.18540.76650.12620.029*
H3A0.37870.72840.13110.029*
N2A0.3894 (8)0.65230 (15)0.06289 (10)0.0229 (13)
H4A0.24140.64320.05790.027*
C1A0.1975 (8)0.7163 (2)0.09304 (11)0.0206 (15)
H11A0.17290.74580.07970.025*
H12A0.05460.69410.09110.025*
C2A0.4222 (8)0.68836 (18)0.08358 (11)0.0183 (15)
C3A0.5944 (9)0.62784 (14)0.04847 (10)0.0239 (16)
H31A0.70090.61390.06480.029*
C4A0.5012 (10)0.58368 (17)0.02936 (12)0.0301 (18)
H41A0.37850.59730.01480.036*
C5A0.3745 (13)0.5454 (2)0.04936 (14)0.0353 (18)
H51A0.24570.56210.06090.053*
H52A0.49170.53060.06340.053*
H53A0.30410.51890.03670.053*
C6A0.6993 (13)0.5588 (2)0.01082 (15)0.048 (2)
H61A0.77540.58390.00240.072*
H62A0.62920.53200.00160.072*
H63A0.82130.54460.02450.072*
C7A0.7441 (8)0.66531 (18)0.02976 (13)0.0278 (17)
O1B0.5819 (8)0.6690 (2)0.23788 (10)0.0408 (14)
O2B0.6172 (7)0.72008 (13)0.16550 (9)0.0219 (11)
O3B0.9606 (6)0.67655 (14)0.16456 (10)0.0230 (11)
N1B0.1862 (10)0.6993 (2)0.26730 (9)0.0272 (14)
H1B0.06860.68610.27940.041*
H2B0.17540.73350.26750.041*
H3B0.33400.68980.27430.041*
N2B0.3838 (8)0.64530 (16)0.19511 (8)0.0235 (13)
H4B0.24180.64050.18650.028*
C1B0.1545 (9)0.6808 (3)0.23598 (12)0.0359 (19)
H11B0.08640.70800.22320.043*
H12B0.03940.65230.23590.043*
C2B0.3943 (9)0.6641 (2)0.22321 (10)0.0252 (16)
C3B0.6024 (8)0.63273 (15)0.17846 (10)0.0200 (15)
H31B0.71040.61310.19230.024*
C4B0.5376 (10)0.59910 (16)0.15142 (11)0.0219 (15)
H41B0.41970.61800.13850.026*
C5B0.4136 (13)0.5512 (2)0.16192 (15)0.042 (2)
H51B0.37050.53070.14420.063*
H52B0.26670.55980.17320.063*
H53B0.52370.53210.17500.063*
C6B0.7551 (11)0.5865 (2)0.13178 (14)0.0364 (19)
H61B0.70330.56560.11470.055*
H62B0.87480.56810.14390.055*
H63B0.82750.61770.12410.055*
C7B0.7386 (8)0.68052 (15)0.16885 (13)0.0184 (15)
O1C0.5635 (7)0.63502 (15)0.38021 (9)0.0284 (11)
O2C0.5706 (8)0.68407 (14)0.30779 (10)0.0256 (11)
O3C0.9152 (7)0.64068 (15)0.30723 (9)0.0262 (11)
N1C0.1991 (10)0.68115 (17)0.40870 (9)0.0191 (12)
H1C0.09140.67020.42290.029*
H2C0.18740.71520.40680.029*
H3C0.35190.67280.41460.029*
N2C0.3436 (7)0.61148 (16)0.33923 (8)0.0177 (12)
H4C0.19710.60530.33230.021*
C1C0.1449 (9)0.6571 (2)0.37919 (11)0.0292 (17)
H11C0.08160.68260.36490.035*
H12C0.01930.63100.38200.035*
C2C0.3708 (8)0.63367 (19)0.36633 (9)0.0154 (14)
C3C0.5534 (8)0.59740 (15)0.32105 (9)0.0194 (15)
H31C0.66210.57590.33370.023*
C4C0.4684 (10)0.56650 (18)0.29373 (11)0.0266 (17)
H41C0.35180.58770.28200.032*
C5C0.3346 (12)0.5197 (2)0.30412 (14)0.0339 (18)
H51C0.20100.52930.31750.051*
H52C0.44640.49760.31510.051*
H53C0.27000.50190.28640.051*
C6C0.6753 (12)0.5525 (3)0.27258 (13)0.0384 (19)
H61C0.75880.58310.26600.058*
H62C0.61080.53480.25490.058*
H63C0.78970.53060.28330.058*
C7C0.6940 (8)0.64488 (16)0.31159 (12)0.0198 (15)
O1D0.6089 (7)0.68049 (15)0.52337 (9)0.0242 (11)
O2D0.6016 (7)0.68173 (13)0.44650 (9)0.0219 (10)
O3D0.9414 (6)0.64067 (14)0.45755 (9)0.0185 (10)
N1D0.2257 (9)0.72095 (17)0.55292 (9)0.0155 (12)
H1D0.12210.70550.56600.023*
H2D0.19650.75460.55290.023*
H3D0.38090.71520.55890.023*
N2D0.3688 (8)0.63394 (15)0.49262 (9)0.0199 (12)
H4D0.21960.62500.48820.024*
C1D0.1889 (9)0.7006 (2)0.52198 (11)0.0189 (15)
H11D0.16430.72860.50750.023*
H12D0.04320.67890.52160.023*
C2D0.4084 (8)0.67038 (18)0.51292 (11)0.0183 (14)
C3D0.5715 (8)0.60896 (13)0.47787 (9)0.0137 (13)
H31D0.67860.59420.49380.016*
C4D0.4742 (9)0.56617 (15)0.45784 (10)0.0151 (14)
H41D0.35790.58110.44300.018*
C5D0.3380 (11)0.52756 (19)0.47671 (13)0.0288 (17)
H51D0.27610.50090.46340.043*
H52D0.20240.54400.48710.043*
H53D0.44770.51290.49180.043*
C6D0.6770 (11)0.5411 (2)0.44002 (12)0.0254 (16)
H61D0.60930.51440.42720.038*
H62D0.79460.52650.45410.038*
H63D0.75760.56620.42720.038*
C7D0.7193 (7)0.64737 (16)0.45933 (11)0.0135 (14)
O1E0.6001 (8)0.68919 (17)0.66735 (10)0.0318 (12)
O2E0.6311 (7)0.71674 (12)0.59262 (9)0.0221 (11)
O3E0.9679 (6)0.67145 (14)0.59615 (10)0.0237 (11)
N1E0.1973 (10)0.71915 (19)0.69669 (9)0.0243 (14)
H1E0.08430.70360.70840.036*
H2E0.17510.75300.69750.036*
H3E0.34790.71140.70360.036*
N2E0.3910 (7)0.65149 (15)0.62945 (9)0.0202 (12)
H4E0.24670.64290.62280.024*
C1E0.1725 (9)0.7019 (3)0.66506 (12)0.0334 (18)
H11E0.12380.73050.65200.040*
H12E0.04510.67580.66380.040*
C2E0.4093 (8)0.6806 (2)0.65404 (10)0.0221 (15)
C3E0.6045 (8)0.63381 (14)0.61355 (10)0.0181 (14)
H31E0.71210.61680.62860.022*
C4E0.5274 (9)0.59464 (16)0.59005 (11)0.0216 (15)
H41E0.40270.61070.57670.026*
C5E0.4101 (13)0.5494 (2)0.60510 (14)0.0383 (19)
H51E0.27730.56070.61820.057*
H52E0.53080.53160.61730.057*
H53E0.34650.52670.58950.057*
C6E0.7344 (11)0.5778 (2)0.56980 (13)0.0345 (18)
H61E0.80810.60730.56010.052*
H62E0.67250.55500.55420.052*
H63E0.85620.56030.58200.052*
C7E0.7460 (7)0.67782 (16)0.59960 (12)0.0176 (15)
O1F0.5668 (7)0.63960 (17)0.80719 (9)0.0295 (12)
O2F0.5873 (8)0.70117 (14)0.73716 (9)0.0278 (11)
O3F0.9299 (7)0.65752 (16)0.73459 (10)0.0307 (12)
N1F0.1901 (10)0.67809 (17)0.83745 (9)0.0177 (12)
H1F0.08380.66530.85120.026*
H2F0.17230.71210.83650.026*
H3F0.34400.67060.84330.026*
N2F0.3564 (8)0.62346 (17)0.76419 (8)0.0246 (13)
H4F0.21160.61960.75620.030*
C1F0.1421 (9)0.6559 (3)0.80735 (11)0.0270 (17)
H11F0.06160.68110.79420.032*
H12F0.03220.62670.80950.032*
C2F0.3760 (8)0.6393 (2)0.79288 (9)0.0223 (15)
C3F0.5689 (9)0.61250 (15)0.74594 (9)0.0223 (15)
H31F0.67760.58980.75780.027*
C4F0.4914 (10)0.58489 (18)0.71692 (10)0.0237 (16)
H41F0.37860.60750.70560.028*
C5F0.3552 (12)0.5369 (2)0.72437 (14)0.0359 (19)
H51F0.30790.52010.70550.054*
H52F0.21010.54520.73620.054*
H53F0.45970.51460.73630.054*
C6F0.7050 (12)0.5735 (2)0.69633 (13)0.0378 (19)
H61F0.64760.55620.67810.057*
H62F0.82040.55190.70710.057*
H63F0.78490.60500.69060.057*
C7F0.7081 (8)0.66133 (16)0.73877 (13)0.0215 (16)
O1G0.5927 (8)0.65189 (18)0.95235 (10)0.0383 (13)
O2G0.5846 (7)0.67127 (12)0.87620 (9)0.0208 (10)
O3G0.9293 (6)0.62970 (14)0.88348 (9)0.0223 (10)
N1G0.2217 (10)0.6979 (2)0.98004 (10)0.0289 (14)
H1G0.12800.68260.99430.043*
H2G0.18480.73120.97920.043*
H3G0.38060.69410.98500.043*
N2G0.3571 (8)0.61279 (16)0.91741 (9)0.0237 (13)
H4G0.20850.60420.91240.028*
C1G0.1755 (10)0.6747 (3)0.95012 (13)0.0354 (19)
H11G0.13990.70120.93500.043*
H12G0.03330.65210.95140.043*
C2G0.3946 (9)0.6451 (2)0.94031 (11)0.0298 (17)
C3G0.5620 (8)0.59193 (14)0.90086 (10)0.0183 (14)
H31G0.66950.57360.91540.022*
C4G0.4703 (9)0.55484 (16)0.87672 (11)0.0221 (15)
H41G0.35650.57350.86310.027*
C5G0.3311 (11)0.51202 (19)0.89109 (14)0.0317 (17)
H51G0.27440.48900.87520.048*
H52G0.19170.52550.90220.048*
H53G0.43690.49380.90510.048*
C6G0.6773 (11)0.5351 (2)0.85726 (13)0.0319 (17)
H61G0.76640.56350.84850.048*
H62G0.61190.51410.84090.048*
H63G0.78690.51490.86980.048*
C7G0.7070 (7)0.63495 (16)0.88592 (12)0.0174 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.019 (2)0.030 (2)0.027 (2)0.003 (2)0.001 (2)0.0059 (19)
O2A0.031 (3)0.048 (3)0.021 (2)0.002 (2)0.000 (2)0.005 (2)
O3A0.023 (3)0.053 (3)0.023 (2)0.002 (2)0.002 (2)0.007 (2)
N1A0.019 (3)0.019 (2)0.020 (3)0.003 (2)0.000 (2)0.001 (2)
N2A0.016 (3)0.030 (3)0.023 (3)0.002 (2)0.001 (2)0.012 (2)
C1A0.016 (3)0.027 (3)0.019 (3)0.004 (3)0.000 (3)0.004 (2)
C2A0.020 (3)0.020 (3)0.015 (3)0.003 (3)0.000 (3)0.001 (2)
C3A0.022 (3)0.028 (3)0.021 (3)0.006 (3)0.002 (3)0.009 (2)
C4A0.027 (3)0.033 (3)0.030 (3)0.002 (3)0.003 (3)0.009 (3)
C5A0.040 (4)0.030 (3)0.036 (3)0.006 (3)0.002 (3)0.015 (3)
C6A0.047 (4)0.054 (4)0.042 (4)0.008 (3)0.006 (3)0.018 (3)
C7A0.024 (4)0.041 (3)0.018 (3)0.000 (3)0.004 (3)0.006 (3)
O1B0.027 (3)0.069 (3)0.027 (2)0.004 (3)0.002 (2)0.000 (2)
O2B0.022 (3)0.022 (2)0.022 (2)0.001 (2)0.001 (2)0.0002 (18)
O3B0.021 (3)0.027 (2)0.021 (2)0.001 (2)0.001 (2)0.0006 (19)
N1B0.020 (3)0.043 (3)0.018 (3)0.001 (3)0.002 (2)0.008 (2)
N2B0.021 (3)0.029 (3)0.021 (3)0.002 (2)0.002 (2)0.002 (2)
C1B0.033 (4)0.052 (4)0.022 (3)0.002 (3)0.000 (3)0.004 (3)
C2B0.022 (3)0.036 (3)0.017 (3)0.003 (3)0.001 (3)0.009 (3)
C3B0.021 (3)0.024 (3)0.015 (3)0.000 (3)0.002 (3)0.005 (2)
C4B0.029 (3)0.019 (3)0.018 (3)0.000 (3)0.003 (3)0.005 (2)
C5B0.046 (4)0.033 (3)0.047 (4)0.008 (3)0.004 (3)0.000 (3)
C6B0.040 (4)0.035 (3)0.034 (3)0.004 (3)0.006 (3)0.003 (3)
C7B0.017 (3)0.025 (3)0.013 (3)0.003 (3)0.002 (2)0.003 (2)
O1C0.024 (3)0.035 (2)0.026 (2)0.001 (2)0.007 (2)0.012 (2)
O2C0.024 (3)0.033 (2)0.020 (2)0.001 (2)0.002 (2)0.0057 (19)
O3C0.023 (3)0.037 (2)0.019 (2)0.003 (2)0.002 (2)0.0003 (19)
N1C0.021 (3)0.019 (2)0.018 (3)0.000 (2)0.002 (2)0.001 (2)
N2C0.016 (2)0.023 (2)0.014 (2)0.0025 (19)0.0015 (19)0.0031 (18)
C1C0.028 (4)0.040 (3)0.019 (3)0.001 (3)0.001 (3)0.007 (3)
C2C0.014 (3)0.018 (3)0.014 (3)0.004 (2)0.000 (2)0.001 (2)
C3C0.018 (3)0.030 (3)0.011 (3)0.002 (3)0.001 (3)0.003 (2)
C4C0.026 (3)0.038 (3)0.016 (3)0.008 (3)0.002 (3)0.012 (3)
C5C0.037 (4)0.041 (3)0.023 (3)0.007 (3)0.001 (3)0.018 (3)
C6C0.039 (4)0.050 (4)0.026 (3)0.005 (3)0.010 (3)0.018 (3)
C7C0.019 (2)0.027 (2)0.014 (2)0.003 (2)0.003 (2)0.0007 (19)
O1D0.016 (2)0.031 (2)0.025 (2)0.000 (2)0.002 (2)0.0079 (19)
O2D0.024 (2)0.020 (2)0.021 (2)0.000 (2)0.007 (2)0.0001 (17)
O3D0.020 (2)0.022 (2)0.014 (2)0.0032 (19)0.0026 (18)0.0019 (17)
N1D0.017 (3)0.018 (2)0.012 (2)0.001 (2)0.002 (2)0.001 (2)
N2D0.020 (2)0.026 (2)0.014 (2)0.0020 (19)0.0010 (18)0.0055 (17)
C1D0.021 (3)0.021 (3)0.015 (3)0.004 (3)0.003 (3)0.001 (2)
C2D0.018 (3)0.024 (2)0.013 (2)0.004 (2)0.002 (2)0.000 (2)
C3D0.014 (2)0.016 (2)0.011 (2)0.001 (2)0.0001 (19)0.0033 (18)
C4D0.016 (2)0.018 (2)0.011 (2)0.0000 (18)0.0029 (18)0.0005 (17)
C5D0.029 (3)0.024 (3)0.033 (3)0.001 (3)0.001 (3)0.003 (3)
C6D0.028 (3)0.026 (3)0.023 (3)0.001 (3)0.005 (3)0.002 (3)
C7D0.015 (2)0.015 (2)0.010 (2)0.0029 (18)0.0007 (18)0.0014 (17)
O1E0.023 (3)0.046 (3)0.027 (2)0.004 (2)0.003 (2)0.005 (2)
O2E0.027 (3)0.018 (2)0.022 (2)0.004 (2)0.004 (2)0.0014 (17)
O3E0.020 (2)0.034 (2)0.018 (2)0.0015 (19)0.0018 (19)0.0086 (19)
N1E0.020 (3)0.032 (3)0.021 (3)0.005 (2)0.005 (2)0.002 (2)
N2E0.018 (3)0.029 (2)0.014 (2)0.002 (2)0.001 (2)0.002 (2)
C1E0.030 (4)0.043 (3)0.027 (3)0.005 (3)0.001 (3)0.007 (3)
C2E0.019 (3)0.028 (3)0.020 (3)0.003 (3)0.003 (3)0.003 (3)
C3E0.021 (3)0.019 (3)0.014 (3)0.001 (3)0.005 (3)0.001 (2)
C4E0.024 (3)0.019 (3)0.021 (3)0.000 (3)0.005 (3)0.001 (2)
C5E0.048 (4)0.033 (3)0.034 (3)0.007 (3)0.003 (3)0.002 (3)
C6E0.044 (4)0.033 (3)0.027 (3)0.007 (3)0.001 (3)0.008 (3)
C7E0.019 (3)0.021 (2)0.013 (2)0.000 (2)0.002 (2)0.002 (2)
O1F0.023 (3)0.047 (3)0.018 (2)0.010 (2)0.003 (2)0.002 (2)
O2F0.026 (3)0.038 (2)0.020 (2)0.001 (2)0.001 (2)0.0038 (19)
O3F0.024 (3)0.045 (3)0.022 (2)0.003 (2)0.001 (2)0.005 (2)
N1F0.016 (2)0.025 (2)0.012 (2)0.0011 (19)0.0017 (19)0.0013 (18)
N2F0.024 (2)0.032 (2)0.018 (2)0.001 (2)0.000 (2)0.0019 (19)
C1F0.026 (4)0.031 (3)0.024 (3)0.000 (3)0.002 (3)0.011 (3)
C2F0.019 (3)0.031 (3)0.016 (3)0.002 (3)0.000 (3)0.000 (3)
C3F0.023 (3)0.030 (3)0.013 (3)0.005 (3)0.000 (3)0.002 (2)
C4F0.028 (3)0.033 (3)0.010 (3)0.008 (3)0.002 (3)0.001 (3)
C5F0.046 (4)0.035 (3)0.027 (3)0.002 (3)0.001 (3)0.001 (3)
C6F0.042 (4)0.043 (3)0.029 (3)0.010 (3)0.003 (3)0.004 (3)
C7F0.018 (3)0.030 (3)0.016 (2)0.004 (2)0.003 (2)0.003 (2)
O1G0.027 (3)0.060 (3)0.028 (2)0.006 (2)0.006 (2)0.012 (2)
O2G0.024 (2)0.0181 (19)0.021 (2)0.0020 (19)0.004 (2)0.0010 (17)
O3G0.017 (2)0.033 (2)0.017 (2)0.0005 (19)0.0003 (19)0.0023 (18)
N1G0.022 (3)0.049 (3)0.015 (3)0.005 (3)0.001 (2)0.001 (2)
N2G0.016 (3)0.037 (3)0.018 (2)0.000 (2)0.002 (2)0.000 (2)
C1G0.036 (4)0.046 (4)0.024 (3)0.008 (3)0.003 (3)0.002 (3)
C2G0.024 (3)0.048 (3)0.018 (3)0.000 (3)0.001 (3)0.001 (3)
C3G0.018 (3)0.021 (3)0.016 (3)0.002 (3)0.003 (3)0.006 (2)
C4G0.023 (3)0.017 (3)0.026 (3)0.000 (2)0.003 (3)0.003 (3)
C5G0.033 (4)0.030 (3)0.032 (3)0.006 (3)0.007 (3)0.009 (3)
C6G0.032 (4)0.035 (3)0.028 (3)0.001 (3)0.000 (3)0.011 (3)
C7G0.018 (3)0.020 (2)0.014 (2)0.002 (2)0.000 (2)0.003 (2)
Geometric parameters (Å, º) top
O1A—C2A1.230 (4)C3D—C4D1.537 (4)
O2A—C7A1.254 (4)C3D—C7D1.542 (4)
O3A—C7A1.247 (4)C3D—H31D1.0000
N1A—C1A1.480 (5)C4D—C6D1.522 (5)
N1A—H1A0.9100C4D—C5D1.520 (5)
N1A—H2A0.9100C4D—H41D1.0000
N1A—H3A0.9100C5D—H51D0.9800
N2A—C2A1.335 (4)C5D—H52D0.9800
N2A—C3A1.452 (4)C5D—H53D0.9800
N2A—H4A0.8800C6D—H61D0.9800
C1A—C2A1.506 (4)C6D—H62D0.9800
C1A—H11A0.9900C6D—H63D0.9800
C1A—H12A0.9900O1E—C2E1.228 (4)
C3A—C7A1.535 (4)O2E—C7E1.252 (4)
C3A—C4A1.534 (5)O3E—C7E1.246 (4)
C3A—H31A1.0000N1E—C1E1.475 (5)
C4A—C6A1.517 (5)N1E—H1E0.9100
C4A—C5A1.517 (5)N1E—H2E0.9100
C4A—H41A1.0000N1E—H3E0.9100
C5A—H51A0.9800N2E—C2E1.336 (4)
C5A—H52A0.9800N2E—C3E1.450 (4)
C5A—H53A0.9800N2E—H4E0.8800
C6A—H61A0.9800C1E—C2E1.506 (5)
C6A—H62A0.9800C1E—H11E0.9900
C6A—H63A0.9800C1E—H12E0.9900
O1B—C2B1.228 (4)C3E—C4E1.529 (4)
O2B—C7B1.256 (4)C3E—C7E1.536 (4)
O3B—C7B1.245 (4)C3E—H31E1.0000
N1B—C1B1.476 (5)C4E—C6E1.518 (5)
N1B—H1B0.9100C4E—C5E1.519 (5)
N1B—H2B0.9100C4E—H41E1.0000
N1B—H3B0.9100C5E—H51E0.9800
N2B—C2B1.337 (4)C5E—H52E0.9800
N2B—C3B1.452 (4)C5E—H53E0.9800
N2B—H4B0.8800C6E—H61E0.9800
C1B—C2B1.507 (5)C6E—H62E0.9800
C1B—H11B0.9900C6E—H63E0.9800
C1B—H12B0.9900O1F—C2F1.229 (4)
C3B—C7B1.536 (4)O2F—C7F1.254 (4)
C3B—C4B1.532 (4)O3F—C7F1.243 (4)
C3B—H31B1.0000N1F—C1F1.476 (5)
C4B—C6B1.519 (5)N1F—H1F0.9100
C4B—C5B1.518 (5)N1F—H2F0.9100
C4B—H41B1.0000N1F—H3F0.9100
C5B—H51B0.9800N2F—C2F1.338 (4)
C5B—H52B0.9800N2F—C3F1.453 (4)
C5B—H53B0.9800N2F—H4F0.8800
C6B—H61B0.9800C1F—C2F1.508 (5)
C6B—H62B0.9800C1F—H11F0.9900
C6B—H63B0.9800C1F—H12F0.9900
O1C—C2C1.228 (4)C3F—C4F1.536 (4)
O2C—C7C1.256 (4)C3F—C7F1.542 (4)
O3C—C7C1.242 (4)C3F—H31F1.0000
N1C—C1C1.480 (5)C4F—C6F1.519 (5)
N1C—H1C0.9100C4F—C5F1.516 (5)
N1C—H2C0.9100C4F—H41F1.0000
N1C—H3C0.9100C5F—H51F0.9800
N2C—C2C1.341 (4)C5F—H52F0.9800
N2C—C3C1.458 (4)C5F—H53F0.9800
N2C—H4C0.8800C6F—H61F0.9800
C1C—C2C1.506 (5)C6F—H62F0.9800
C1C—H11C0.9900C6F—H63F0.9800
C1C—H12C0.9900O1G—C2G1.230 (4)
C3C—C4C1.531 (4)O2G—C7G1.254 (4)
C3C—C7C1.539 (4)O3G—C7G1.241 (4)
C3C—H31C1.0000N1G—C1G1.479 (5)
C4C—C6C1.521 (5)N1G—H1G0.9100
C4C—C5C1.519 (5)N1G—H2G0.9100
C4C—H41C1.0000N1G—H3G0.9100
C5C—H51C0.9800N2G—C2G1.341 (4)
C5C—H52C0.9800N2G—C3G1.457 (4)
C5C—H53C0.9800N2G—H4G0.8800
C6C—H61C0.9800C1G—C2G1.507 (5)
C6C—H62C0.9800C1G—H11G0.9900
C6C—H63C0.9800C1G—H12G0.9900
O1D—C2D1.229 (4)C3G—C4G1.537 (5)
O2D—C7D1.256 (4)C3G—C7G1.544 (4)
O3D—C7D1.242 (4)C3G—H31G1.0000
N1D—C1D1.481 (5)C4G—C5G1.512 (5)
N1D—H1D0.9100C4G—C6G1.524 (5)
N1D—H2D0.9100C4G—H41G1.0000
N1D—H3D0.9100C5G—H51G0.9800
N2D—C2D1.337 (4)C5G—H52G0.9800
N2D—C3D1.455 (4)C5G—H53G0.9800
N2D—H4D0.8800C6G—H61G0.9800
C1D—C2D1.508 (5)C6G—H62G0.9800
C1D—H11D0.9900C6G—H63G0.9800
C1D—H12D0.9900
C1A—N1A—H1A109.5C7D—C3D—H31D108.7
C1A—N1A—H2A109.5C6D—C4D—C5D110.5 (4)
H1A—N1A—H2A109.5C6D—C4D—C3D111.3 (4)
C1A—N1A—H3A109.5C5D—C4D—C3D111.0 (3)
H1A—N1A—H3A109.5C6D—C4D—H41D107.9
H2A—N1A—H3A109.5C5D—C4D—H41D107.9
C2A—N2A—C3A121.0 (4)C3D—C4D—H41D107.9
C2A—N2A—H4A119.5C4D—C5D—H51D109.5
C3A—N2A—H4A119.5C4D—C5D—H52D109.5
N1A—C1A—C2A109.4 (4)H51D—C5D—H52D109.5
N1A—C1A—H11A109.8C4D—C5D—H53D109.5
C2A—C1A—H11A109.8H51D—C5D—H53D109.5
N1A—C1A—H12A109.8H52D—C5D—H53D109.5
C2A—C1A—H12A109.8C4D—C6D—H61D109.5
H11A—C1A—H12A108.2C4D—C6D—H62D109.5
O1A—C2A—N2A123.6 (4)H61D—C6D—H62D109.5
O1A—C2A—C1A120.8 (3)C4D—C6D—H63D109.5
N2A—C2A—C1A115.6 (4)H61D—C6D—H63D109.5
N2A—C3A—C7A111.4 (3)H62D—C6D—H63D109.5
N2A—C3A—C4A108.7 (3)O3D—C7D—O2D126.0 (4)
C7A—C3A—C4A112.5 (4)O3D—C7D—C3D117.5 (4)
N2A—C3A—H31A108.0O2D—C7D—C3D116.5 (3)
C7A—C3A—H31A108.0C1E—N1E—H1E109.5
C4A—C3A—H31A108.0C1E—N1E—H2E109.5
C6A—C4A—C5A110.8 (4)H1E—N1E—H2E109.5
C6A—C4A—C3A112.8 (4)C1E—N1E—H3E109.5
C5A—C4A—C3A110.4 (4)H1E—N1E—H3E109.5
C6A—C4A—H41A107.6H2E—N1E—H3E109.5
C5A—C4A—H41A107.6C2E—N2E—C3E121.3 (4)
C3A—C4A—H41A107.6C2E—N2E—H4E119.4
C4A—C5A—H51A109.5C3E—N2E—H4E119.4
C4A—C5A—H52A109.5N1E—C1E—C2E110.0 (4)
H51A—C5A—H52A109.5N1E—C1E—H11E109.7
C4A—C5A—H53A109.5C2E—C1E—H11E109.7
H51A—C5A—H53A109.5N1E—C1E—H12E109.7
H52A—C5A—H53A109.5C2E—C1E—H12E109.7
C4A—C6A—H61A109.5H11E—C1E—H12E108.2
C4A—C6A—H62A109.5O1E—C2E—N2E124.1 (4)
H61A—C6A—H62A109.5O1E—C2E—C1E121.5 (4)
C4A—C6A—H63A109.5N2E—C2E—C1E114.5 (4)
H61A—C6A—H63A109.5N2E—C3E—C4E108.8 (3)
H62A—C6A—H63A109.5N2E—C3E—C7E111.1 (3)
O2A—C7A—O3A125.7 (4)C4E—C3E—C7E112.9 (3)
O2A—C7A—C3A117.3 (4)N2E—C3E—H31E108.0
O3A—C7A—C3A117.0 (4)C4E—C3E—H31E108.0
C1B—N1B—H1B109.5C7E—C3E—H31E108.0
C1B—N1B—H2B109.5C6E—C4E—C5E110.2 (4)
H1B—N1B—H2B109.5C6E—C4E—C3E112.9 (4)
C1B—N1B—H3B109.5C5E—C4E—C3E111.2 (4)
H1B—N1B—H3B109.5C6E—C4E—H41E107.4
H2B—N1B—H3B109.5C5E—C4E—H41E107.4
C2B—N2B—C3B121.2 (4)C3E—C4E—H41E107.4
C2B—N2B—H4B119.4C4E—C5E—H51E109.5
C3B—N2B—H4B119.4C4E—C5E—H52E109.5
N1B—C1B—C2B110.1 (4)H51E—C5E—H52E109.5
N1B—C1B—H11B109.6C4E—C5E—H53E109.5
C2B—C1B—H11B109.6H51E—C5E—H53E109.5
N1B—C1B—H12B109.6H52E—C5E—H53E109.5
C2B—C1B—H12B109.6C4E—C6E—H61E109.5
H11B—C1B—H12B108.2C4E—C6E—H62E109.5
O1B—C2B—N2B124.3 (4)H61E—C6E—H62E109.5
O1B—C2B—C1B120.9 (4)C4E—C6E—H63E109.5
N2B—C2B—C1B114.7 (4)H61E—C6E—H63E109.5
N2B—C3B—C7B110.9 (3)H62E—C6E—H63E109.5
N2B—C3B—C4B109.4 (3)O2E—C7E—O3E125.5 (4)
C7B—C3B—C4B112.5 (3)O2E—C7E—C3E118.0 (3)
N2B—C3B—H31B108.0O3E—C7E—C3E116.5 (4)
C7B—C3B—H31B108.0C1F—N1F—H1F109.5
C4B—C3B—H31B108.0C1F—N1F—H2F109.5
C6B—C4B—C5B110.2 (4)H1F—N1F—H2F109.5
C6B—C4B—C3B112.8 (4)C1F—N1F—H3F109.5
C5B—C4B—C3B111.0 (4)H1F—N1F—H3F109.5
C6B—C4B—H41B107.5H2F—N1F—H3F109.5
C5B—C4B—H41B107.5C2F—N2F—C3F121.4 (4)
C3B—C4B—H41B107.5C2F—N2F—H4F119.3
C4B—C5B—H51B109.5C3F—N2F—H4F119.3
C4B—C5B—H52B109.5N1F—C1F—C2F110.1 (4)
H51B—C5B—H52B109.5N1F—C1F—H11F109.6
C4B—C5B—H53B109.5C2F—C1F—H11F109.6
H51B—C5B—H53B109.5N1F—C1F—H12F109.6
H52B—C5B—H53B109.5C2F—C1F—H12F109.6
C4B—C6B—H61B109.5H11F—C1F—H12F108.2
C4B—C6B—H62B109.5O1F—C2F—N2F123.9 (4)
H61B—C6B—H62B109.5O1F—C2F—C1F121.1 (3)
C4B—C6B—H63B109.5N2F—C2F—C1F115.0 (4)
H61B—C6B—H63B109.5N2F—C3F—C4F109.4 (3)
H62B—C6B—H63B109.5N2F—C3F—C7F110.3 (3)
O2B—C7B—O3B125.4 (4)C4F—C3F—C7F111.7 (3)
O2B—C7B—C3B117.6 (3)N2F—C3F—H31F108.4
O3B—C7B—C3B117.0 (4)C4F—C3F—H31F108.4
C1C—N1C—H1C109.5C7F—C3F—H31F108.4
C1C—N1C—H2C109.5C6F—C4F—C5F110.3 (4)
H1C—N1C—H2C109.5C6F—C4F—C3F112.1 (4)
C1C—N1C—H3C109.5C5F—C4F—C3F111.1 (4)
H1C—N1C—H3C109.5C6F—C4F—H41F107.7
H2C—N1C—H3C109.5C5F—C4F—H41F107.7
C2C—N2C—C3C120.9 (4)C3F—C4F—H41F107.7
C2C—N2C—H4C119.5C4F—C5F—H51F109.5
C3C—N2C—H4C119.5C4F—C5F—H52F109.5
N1C—C1C—C2C110.0 (4)H51F—C5F—H52F109.5
N1C—C1C—H11C109.7C4F—C5F—H53F109.5
C2C—C1C—H11C109.7H51F—C5F—H53F109.5
N1C—C1C—H12C109.7H52F—C5F—H53F109.5
C2C—C1C—H12C109.7C4F—C6F—H61F109.5
H11C—C1C—H12C108.2C4F—C6F—H62F109.5
O1C—C2C—N2C123.6 (4)H61F—C6F—H62F109.5
O1C—C2C—C1C121.2 (3)C4F—C6F—H63F109.5
N2C—C2C—C1C115.1 (3)H61F—C6F—H63F109.5
N2C—C3C—C4C109.1 (3)H62F—C6F—H63F109.5
N2C—C3C—C7C109.9 (3)O2F—C7F—O3F125.8 (4)
C4C—C3C—C7C112.4 (3)O2F—C7F—C3F117.2 (4)
N2C—C3C—H31C108.5O3F—C7F—C3F117.0 (4)
C4C—C3C—H31C108.5C1G—N1G—H1G109.5
C7C—C3C—H31C108.5C1G—N1G—H2G109.5
C6C—C4C—C5C110.5 (4)H1G—N1G—H2G109.5
C6C—C4C—C3C112.5 (4)C1G—N1G—H3G109.5
C5C—C4C—C3C110.6 (4)H1G—N1G—H3G109.5
C6C—C4C—H41C107.7H2G—N1G—H3G109.5
C5C—C4C—H41C107.7C2G—N2G—C3G120.0 (4)
C3C—C4C—H41C107.7C2G—N2G—H4G120.0
C4C—C5C—H51C109.5C3G—N2G—H4G120.0
C4C—C5C—H52C109.5N1G—C1G—C2G109.6 (4)
H51C—C5C—H52C109.5N1G—C1G—H11G109.7
C4C—C5C—H53C109.5C2G—C1G—H11G109.7
H51C—C5C—H53C109.5N1G—C1G—H12G109.7
H52C—C5C—H53C109.5C2G—C1G—H12G109.7
C4C—C6C—H61C109.5H11G—C1G—H12G108.2
C4C—C6C—H62C109.5O1G—C2G—N2G123.8 (4)
H61C—C6C—H62C109.5O1G—C2G—C1G120.9 (4)
C4C—C6C—H63C109.5N2G—C2G—C1G115.2 (4)
H61C—C6C—H63C109.5N2G—C3G—C4G109.6 (3)
H62C—C6C—H63C109.5N2G—C3G—C7G109.6 (3)
O3C—C7C—O2C126.0 (4)C4G—C3G—C7G110.5 (3)
O3C—C7C—C3C117.7 (4)N2G—C3G—H31G109.0
O2C—C7C—C3C116.2 (4)C4G—C3G—H31G109.0
C1D—N1D—H1D109.5C7G—C3G—H31G109.0
C1D—N1D—H2D109.5C5G—C4G—C6G111.0 (4)
H1D—N1D—H2D109.5C5G—C4G—C3G111.1 (4)
C1D—N1D—H3D109.5C6G—C4G—C3G111.3 (4)
H1D—N1D—H3D109.5C5G—C4G—H41G107.7
H2D—N1D—H3D109.5C6G—C4G—H41G107.7
C2D—N2D—C3D120.3 (4)C3G—C4G—H41G107.7
C2D—N2D—H4D119.9C4G—C5G—H51G109.5
C3D—N2D—H4D119.9C4G—C5G—H52G109.5
N1D—C1D—C2D109.2 (3)H51G—C5G—H52G109.5
N1D—C1D—H11D109.8C4G—C5G—H53G109.5
C2D—C1D—H11D109.8H51G—C5G—H53G109.5
N1D—C1D—H12D109.8H52G—C5G—H53G109.5
C2D—C1D—H12D109.8C4G—C6G—H61G109.5
H11D—C1D—H12D108.3C4G—C6G—H62G109.5
O1D—C2D—N2D123.8 (4)H61G—C6G—H62G109.5
O1D—C2D—C1D120.6 (4)C4G—C6G—H63G109.5
N2D—C2D—C1D115.6 (4)H61G—C6G—H63G109.5
N2D—C3D—C4D109.0 (3)H62G—C6G—H63G109.5
N2D—C3D—C7D110.0 (3)O3G—C7G—O2G126.2 (4)
C4D—C3D—C7D111.8 (3)O3G—C7G—C3G117.8 (4)
N2D—C3D—H31D108.7O2G—C7G—C3G115.9 (3)
C4D—C3D—H31D108.7
C3A—N2A—C2A—O1A8.7 (9)C7D—C3D—C4D—C6D54.0 (5)
C3A—N2A—C2A—C1A170.5 (5)N2D—C3D—C4D—C5D60.6 (5)
N1A—C1A—C2A—O1A31.0 (8)C7D—C3D—C4D—C5D177.6 (4)
N1A—C1A—C2A—N2A149.7 (5)N2D—C3D—C7D—O3D146.6 (5)
C2A—N2A—C3A—C7A63.3 (6)C4D—C3D—C7D—O3D92.2 (6)
C2A—N2A—C3A—C4A172.3 (5)N2D—C3D—C7D—O2D35.8 (6)
N2A—C3A—C4A—C6A174.2 (5)C4D—C3D—C7D—O2D85.4 (5)
C7A—C3A—C4A—C6A50.4 (6)C3E—N2E—C2E—O1E10.0 (9)
N2A—C3A—C4A—C5A61.3 (6)C3E—N2E—C2E—C1E171.4 (5)
C7A—C3A—C4A—C5A174.8 (5)N1E—C1E—C2E—O1E16.7 (9)
N2A—C3A—C7A—O2A30.5 (7)N1E—C1E—C2E—N2E161.9 (5)
C4A—C3A—C7A—O2A91.9 (6)C2E—N2E—C3E—C4E170.5 (5)
N2A—C3A—C7A—O3A149.7 (5)C2E—N2E—C3E—C7E64.6 (6)
C4A—C3A—C7A—O3A87.9 (6)N2E—C3E—C4E—C6E173.8 (4)
C3B—N2B—C2B—O1B5.3 (10)C7E—C3E—C4E—C6E50.0 (6)
C3B—N2B—C2B—C1B173.1 (5)N2E—C3E—C4E—C5E61.7 (5)
N1B—C1B—C2B—O1B3.3 (10)C7E—C3E—C4E—C5E174.4 (4)
N1B—C1B—C2B—N2B178.2 (5)N2E—C3E—C7E—O2E27.5 (6)
C2B—N2B—C3B—C7B71.1 (6)C4E—C3E—C7E—O2E95.1 (5)
C2B—N2B—C3B—C4B164.3 (5)N2E—C3E—C7E—O3E152.7 (5)
N2B—C3B—C4B—C6B176.9 (5)C4E—C3E—C7E—O3E84.8 (6)
C7B—C3B—C4B—C6B53.2 (6)C3F—N2F—C2F—O1F9.7 (9)
N2B—C3B—C4B—C5B58.9 (6)C3F—N2F—C2F—C1F171.8 (5)
C7B—C3B—C4B—C5B177.4 (5)N1F—C1F—C2F—O1F8.3 (9)
N2B—C3B—C7B—O2B26.3 (6)N1F—C1F—C2F—N2F173.3 (5)
C4B—C3B—C7B—O2B96.6 (5)C2F—N2F—C3F—C4F168.1 (5)
N2B—C3B—C7B—O3B154.8 (5)C2F—N2F—C3F—C7F68.5 (6)
C4B—C3B—C7B—O3B82.3 (6)N2F—C3F—C4F—C6F178.5 (5)
C3C—N2C—C2C—O1C14.4 (8)C7F—C3F—C4F—C6F56.0 (6)
C3C—N2C—C2C—C1C166.0 (5)N2F—C3F—C4F—C5F57.6 (6)
N1C—C1C—C2C—O1C1.5 (8)C7F—C3F—C4F—C5F179.9 (4)
N1C—C1C—C2C—N2C178.9 (5)N2F—C3F—C7F—O2F29.3 (6)
C2C—N2C—C3C—C4C172.1 (5)C4F—C3F—C7F—O2F92.7 (5)
C2C—N2C—C3C—C7C64.3 (6)N2F—C3F—C7F—O3F151.9 (5)
N2C—C3C—C4C—C6C177.0 (5)C4F—C3F—C7F—O3F86.1 (6)
C7C—C3C—C4C—C6C54.9 (6)C3G—N2G—C2G—O1G13.9 (10)
N2C—C3C—C4C—C5C58.9 (6)C3G—N2G—C2G—C1G164.2 (5)
C7C—C3C—C4C—C5C179.0 (5)N1G—C1G—C2G—O1G17.1 (10)
N2C—C3C—C7C—O3C151.6 (5)N1G—C1G—C2G—N2G164.8 (6)
C4C—C3C—C7C—O3C86.8 (6)C2G—N2G—C3G—C4G178.0 (5)
N2C—C3C—C7C—O2C31.3 (6)C2G—N2G—C3G—C7G60.6 (6)
C4C—C3C—C7C—O2C90.3 (5)N2G—C3G—C4G—C5G60.0 (5)
C3D—N2D—C2D—O1D10.0 (8)C7G—C3G—C4G—C5G179.1 (4)
C3D—N2D—C2D—C1D168.1 (4)N2G—C3G—C4G—C6G175.7 (4)
N1D—C1D—C2D—O1D28.4 (8)C7G—C3G—C4G—C6G54.8 (5)
N1D—C1D—C2D—N2D153.4 (5)N2G—C3G—C7G—O3G147.1 (5)
C2D—N2D—C3D—C4D175.4 (5)C4G—C3G—C7G—O3G92.1 (6)
C2D—N2D—C3D—C7D61.8 (6)N2G—C3G—C7G—O2G35.9 (6)
N2D—C3D—C4D—C6D175.8 (4)C4G—C3G—C7G—O2G85.0 (5)

Experimental details

Crystal data
Chemical formulaC7H14N2O3
Mr174.20
Crystal system, space groupOrthorhombic, P212121
Temperature (K)105
a, b, c (Å)5.5238 (7), 26.581 (3), 44.093 (5)
V3)6474.0 (14)
Z28
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.75 × 0.25 × 0.01
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
35141, 6579, 4122
Rint0.125
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.073, 0.172, 1.28
No. of reflections6579
No. of parameters765
No. of restraints1101
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.35

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2001), SAINT, SHELXTL (Bruker, 2000), SHELXTL.

Torsion angles (°) for the seven independent peptide molecules in (I), corresponding torsion angles for Gly-L-Leu (Pattabhi et al., 1974), and r.m.s. values (Å) compared with the average structure of (I) top
Torsion angleABCDEFGMeanaGly-L-Leu
N1-C1-C2-N2 (ψ1)149.7 (5)178.2 (5)-178.9 (5)153.4 (5)162.1 (5)-173.3 (5)164.2 (5)167.9(14.3)171.6
C1-C2-N2-C3 (ω1)170.5 (5)173.1 (5)166.0 (5)168.1 (4)171.4 (5)171.8 (5)164.2 (5)169.3(3.4)168.7
C2-N2-C3-C7 (ϕ2)-63.3 (6)-71.1 (6)-64.3 (6)-61.8 (6)-64.6 (6)-68.5 (6)-60.6 (6)-64.9(3.7)-64.9
N2-C3-C7-O2 (ψT)-30.5 (7)-26.3 (6)-31.3 (6)-35.8 (6)-27.5 (6)-29.3 (6)-35.9 (6)-31.0(3.7)-30.2
N2-C3-C4-C5 (χ21,1)-61.3 (6)-58.9 (6)-58.9 (6)-60.6 (5)-61.7 (5)-57.6 (6)-60.0 (5)-59.9(1.5)
N2-C3-C4-C6 (χ21,1)174.2 (5)176.9 (5)177.0 (5)175.8 (4)173.8 (4)178.5 (5)175.7 (4)176.0(1.6)
H3-N1-C1-C210.2-14.1-8.08.7-4.0-13.79.5-1.6(10.9)-1.9
RMS0.1050.0600.1060.0850.0490.0990.0910.032b
Notes: (a) Sample standard deviation in parenthesis. (b) Calculated for main-chain atoms and C2β.
Hydrogen-bond geometry (Å, °) for (I) and for corresponding interactions in the crystal structure of Gly-L-Leu (Pattabhi et al., 1974). Covalent N—H distances were set to 0.91 Å for amino groups and 0.88 Å for peptide bond amide groups. top
D—H···AMoleculesaMeanGly-L-Leu
N1—H1···O3A···BiB···CiC···DiD···EiE···FiF···GiG···Aii
H···O1.831.921.911.821.891.911.851.871.85
N···O2.727 (6)2.788 (6)2.797 (6)2.719 (6)2.768 (7)2.802 (6)2.751 (7)2.7652.750
N-H···O171159165169162166172166170
N1-H2···O2A···GiiiB···FiiiC···EiiiD···DiiiE···CiiiF···BiiiG···Aiii
H···O1.751.821.841.771.781.831.811.801.80
N···O2.652 (6)2.707 (7)2.741 (6)2.676 (6)2.673 (6)2.740 (6)2.714 (7)2.7002.704
N-H···O171166172173165177173171174
N1-H3···O2A···BB···CC···DD···EE···FF···GG···Aiv
H···O2.021.981.992.032.001.972.032.002.05
N···O2.840 (6)2.804 (7)2.779 (6)2.845 (6)2.838 (7)2.775 (6)2.830 (7)2.8162.856
N-H···O149151145148152147146148147
N2-H4···O3A···AiB···BiC···CiD···DiE···EiF···FiG···Gi
H···O2.072.072.132.092.082.082.112.092.15
N···O2.820 (6)2.823 (6)2.862 (6)2.828 (6)2.811 (6)2.841 (6)2.832 (6)2.8312.870
N-H···O143144140141140143139142139
Note: (a) Donor molecule···acceptor molecule; for designators see Fig. 1. Symmetry codes: (i) x − 1, y, z; (ii) x − 1, y, z + 1; (iii) x − 1/2, 3/2 − y, 1 − z; (iv) x, y, z + 1.
 

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