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The title compounds are cytosine-incorporating hybrid dipeptides showing affinities for 9-ethyl-7-methyl­guanine (7mG). Four mol­ecules of the L-phenyl­alanine (L-Phe) derivative, C16H14N4O4, are present in the asymmetric unit, with similar folded conformations but with slightly different torsion angles involving the L-Phe group. The L-serine (L-Ser) derivative crystallizes as a monohydrate, C10H14N4O5·H2O, the two independent mol­ecules having extended conformations, whereas the two independent mol­ecules of the L-lysine (L-Lys) system in the final compound, C13H21N5O4, are folded. The cytosine–cytosine base pair (pyrimidine N...N inter­actions) was observed only for the L-lysine derivative. Conformational comparisons with previous structures of cytosine hybrid dipeptides may show the relationships between side-chain position and binding phases for 7mG.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105026259/gg1264sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105026259/gg1264Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105026259/gg1264IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105026259/gg1264IIIsup4.hkl
Contains datablock III

CCDC references: 288622; 288623; 288624

Comment top

Nucleic acid-incorporated peptides have been designed with the expectation that the incorporated amino acids could potentially strengthen interactions with complementary bases (Williams et al., 1977; Voet, 1980). We have focused on the cytosine base and designed hybrid peptides (Tarui et al., 1996). The cytosine-incorporated dipeptides have shown affinities for 7-methyl-9-ethylguanine (7 mG) but not for 9-ethylguanine (Asano et al., 2002). The incorporated amino acids affect the association constants between the dipeptides and 7 mG (0.2–6.6 × 10−6 M−1) and induce different binding phases at low and high peptide concentrations. To analyze the fundamental characteristics of cytosine hybrid dipeptides, the structures of the title compounds, (I)–(III), have been determined.

Four molecules of (I) are present in the asymmetric unit (molecules AD), with similar folded conformations (Fig. 1). Slight disorder is observed for the phenyl ring of C, with approximately 4% occupancy for the minor site. No significant difference is observed for the carboxyl C18n—O18n and C18n—O19n bond lengths (n = AD), and a zwitterion form with N3-quarternization is established for molecules AD. Rotations about the C10n–C11n and C11n–C12n bonds mainly contribute to the different orientations between the pyrimidine and phenyl rings in the independent molecules (Table 1). The angles between the least-squares planes of the rings are 38.8 (2), 57.8 (2), 31.2 (3) and 27.8 (2)° for A, B, C (major part) and D, respectively, with intramolecular distances of, respectively, 4.401 (4), 4.683 (3), 4.392 (4) and 4.380 (3) Å between the centroids of the pyrimidine and phenyl rings, indicative of no intramolecular interaction between the aromatic rings. A similar folding was found in the structure of (2-carboxyethyl)-cytosine-1-yl-L-tyrosine, (IV) (Doi, Miyako et al., 1999). A complicated hydrogen-bonding scheme is observed for (I) (Table 2). Atoms N3n and N4n of the cytosine base interact with the carboxyl group atoms O18n and O19n (Fig. 2). These pairings form eight-membered rings between molecules A and D(x, y + 1, z), B and C(x + 1, y, z − 1), C and B, and D and A(x − 1, y − 1, z + 1), with r.m.s. deviations of 1/4, 0.23, 0.17 and 0.15 Å, respectively. Atoms N4n of molecules B, C and D are hydrogen bonded to two acceptor atoms, but atom N4A (molecule A) has one acceptor atom (O19D). Consequently, molecule A has three hydrogen-bond donors, and molecules B, C and D have four (Table 2). These differences are related to acceptor atoms, because the numbers of hydrogen-bond acceptor atoms are 5, 4, 3 and 3 for molecules A, B, C and D, respectively. The independent molecules having slightly different conformations form this unique hydrogen-bonding network with no solvent molecules.

The two independent molecules of (II) (A and B) crystallize in a monohydrate form with a extended conformation (Fig. 3). In molecules A and B, the rotations of the N1m—C7m bonds are inverse to one another [74.2 (4) and −80.8 (4)°, for m = A and B, respectively, in Table 3], and the dispositions of the L-Ser moieties are different for the base planes. The extended structures are induced by the trans positions of the C7m—C8m bond, viz. −178.1 (3) and −179.9 (3)° for A and B, respectively. The (2-carboxyethyl)-cytosine-1-yl-L-threonine (V) also crystallizes as a monohydrated form, but the syn position of the C7—C8 bond results in an L-figure conformation (N1—C7—C8—C9 = 112.5 (3) and 113.3 (3)°; Doi, Asano & Ishida, 1999). The structures of (II) are rather similar to the extended structures of (2-carboxyethyl)-cytosine-1-yl-L-tryptophan, (V) (N1—C7—C8—C9 = −175.4 (4) and −179.4 (4)°; Doi, Tarui et al., 1998). Hydrogen bonds between the cytosine base and the carboxyl group are formed between symmetry-related molecules A (N3A···O13Ai and N4A···O12Ai), indicating the zwitterion form; in addition the C12—O12 and C12—O13 bond lengths are similar (Fig. 3 and Table 4). Atom N4A also interacts with atom O13B of the adjacent molecule B. The hydroxy group of molecule A (O11A) interacts with the carboxyl group of molecule B (O12B) and a water molecule (O1C). Similar hydrogen-bonds are observed for symmetry-related molecules B. The water molecule O1C bridges two molecules A, which translate along (100) (as O9A···O1C···O11Avi), and the water molecule O1D similarly bridges molecules B (O9Bvi···O1D..·O11B; symmetry code as in Table 4).

Two independent molecules of (III) (A and B) are also present in the asymmetric unit, with a folded form (Fig. 5). Molecules A and B are related by pseudosymmetry that fits 95% of the atoms of both molecules, but they are distinguished by some bond rotations (Table 5); the rotations of the N1o–C7o bonds induce different foldings for the base plane, viz. −77.3 (2) and 75.1 (3)° for o = A and B, respectively. Moreover, the Lys side chains are expanded over the base planes in a similar manner in A and B. These conformations are also different at the terminal ε-amino groups; the C12—C13—C14—N14 torsion angles are −62.3 (3) and 73.6 (3)° for A and B, respectively. Cytosine–cytosine base pairings (N4A···N3B and N4B···N3A) are formed between molecules A and B (Table 6 and Fig. 6), a phenomenon that has not been observed in the structures of cytosine-hybrid dipeptides. This base pair indicates a unionized state of N3. The ε-amino groups (N14A and N14B) interact with carboxyl groups (Table 6), and ionized states are established for the carboxyl and ε-amino groups.

The independent molecules of each dipeptide have been fitted to the cytosine base (Fig. 7). The phenyl rings of (I) are located at one side of the cytosine base plane, but the side chains of (II) are separated from the base. The long side chains of (III) are located over the base, positioned on both sides of the base plane. When the positions of the amino acid side chain are defined as sites O and S, as shown in Fig. 7, the present and previously reported structures of cytosine-hybrid peptides are classified as listed in Table 7.

The side chains of (I), (III) and (IV) are located on site O, and the single folding to site O+ is observed for the aromatic analogues (I) and (IV). Compound (VI) also has an aromatic side chain, but the side chain position is S±. In (VI), intermolecular ππ interactions are observed between cytosine bases and indole rings (Doi, Tarui et al., 1998). This interaction seems to affect for the side-chain position of (IV). The side chains of (II) and (2-carboxyethyl)-cytosine-1-yl-L-isoleucine, (VII) (Doi, Tsunemichi et al., 1999), are folded to site S, but single folding to site S– is only observed for (VII). The side chains of (V) and (2-carboxyethyl)-cytosine-1-yl-L-alanine, (VIII) (Doi, Tarui et al., 1999) are expanded approximately perpendicular to the base plane (site 0±). We can postulate relations between these folding positions and the associate constants with 7 mG, but unfortunately find no clear pattern. However, the side chain position may be related to binding phases, because the two binding phases are observed for (I), (II), (IV), and (V). The hybrid dipeptides showing the two binding phases interact with 7 mG at the extra place(s) in addition to cytosine base. The hydroxyl groups of (II) and (V) separated from the cytosine base (sites S or 0) are suitable to interact with 7 mG molecules. The folding forms of (I) and (IV) have the space between the aromatic ring and base, which would accept a 7 mG molecule.

Experimental top

The syntheses were carried out as described previously (Tarui et al., 1996). L-Amino acids were used for the syntheses of (I), (II) and (III). Crystals of (I) and (II) were grown from aqueous hexylenglycol solutions. Crystals of (III) were grown from aqueous DMF solutions. Each peptide (8–10 mg) was dissolved in the organic solvent (0.3–0.4 ml) with heating and 1–2 drops of water (50–100 µl) were added to the solution. Crystals were grown over periods of between two weeks and a month.

Refinement top

H atoms of hydrated water molecules of (II) were found from the differential Fourier map by considering hydrogen bonds. These H atoms were not restrained during refinements. H atoms were treated as riding atoms, with C—H distances of 0.95–1.00 Å, N—H distances of 0.88 (CONH) or 0.91 Å (NH3), and O—H distances of 0.84 Å. In the absence of any significant anomalous scattering, the Flack (1983) parameter was meaningless (Flack & Bernardinelli, 2000). Hence, the Friedel equivalents were merged prior to the final refinements, and the absolute structure was set by reference to the known chirality of the amino acid employed. Validation check suggested pseudosymmetry for (III), but the material chirality (L-Lys) was confirmed in the structure.

Computing details top

For all compounds, data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1998). Program(s) used to solve structure: SHELXD (Sheldrick, 1990b) for (I); SHELXS97 (Sheldrick, 1990a) for (II), (III). For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: Mercury (Bruno et al., 2002).

Figures top
[Figure 1] Fig. 1. The structures of the molecules of (I), with displacement ellipsoids at the 50% probability level. The four independent molecules in the asymmetric unit are depicted and projected from a similar axis. The phenyl ring of molecule C is disorderd over two sites, and the minor part has been drawn using dotted lines.
[Figure 2] Fig. 2. A packing diagram for (I) (Mercury; Bruno et al., 2002), viewed along (100). Molecules AD are labeled at the cytosine base. Dotted lines represent hydrogen bonds. The minor part of the disordered phenyl ring is represented by crosses. The asterisk (*) represents the symmetry operation (x, 1 + y, z).
[Figure 3] Fig. 3. The structures of the molecules of (II), with displacement ellipsoids at the 40% probability level. Two independent molecules are present in the asymmetric unit, with two water molecules (O1C and O1D); dashed lines represent hydrogen bonds.
[Figure 4] Fig. 4. A packing diagram for (II) (Mercury; Bruno et al., 2002), viewed along (100). Molecules A and B are labeled at the cytosine base; dotted lines represent hydrogen bonds. Characters * and # represent the symmetry operations (x + 1, y − 1, z) and (x − 1, y − 1, z), respectively. Crosses represent overlapped atoms along the projection axis.
[Figure 5] Fig. 5. The structures of two independent molecules molecules of (III), with displacement ellipsoids at the 50% probability level.
[Figure 6] Fig. 6. A packing diagram for (III) (Mercury; Bruno et al., 2002), viewed along (100). Molecules A and B are labeled at cytosine base; dotted lines represent hydrogen bonds. Asterisks (*) represent the symmetry operations (x + 1, y + 1, z). Crosses represent overlapped atoms along the projection axis.
[Figure 7] Fig. 7. Fits (iMol; Rotkiewicz, 2004) to the cytosine base and the side-chain folding for the base; the minor part of disordered phenyl ring of (I) is not shown.
(I) N-[2-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)propionyl]-L-phenylalanine top
Crystal data top
C16H18N4O4Z = 4
Mr = 330.34F(000) = 696
Triclinic, P1Dx = 1.353 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3587 (12) ÅCell parameters from 2719 reflections
b = 10.3445 (13) Åθ = 2.2–27.9°
c = 16.925 (2) ŵ = 0.10 mm1
α = 92.079 (2)°T = 100 K
β = 95.775 (2)°Plate, colourless
γ = 95.245 (2)°0.25 × 0.20 × 0.04 mm
V = 1621.7 (4) Å3
Data collection top
Bruker SMART APEX
diffractometer
6059 independent reflections
Radiation source: MacSciences M18XCE rotating anode5788 reflections with I > \2s(I)
Graphite monochromatorRint = 0.025
Detector resolution: 8.366 pixels mm-1θmax = 25.7°, θmin = 2.0°
ω scansh = 911
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1212
Tmin = 0.832, Tmax = 0.998l = 2016
8913 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0753P)2 + 0.9676P]
where P = (Fo2 + 2Fc2)/3
6059 reflections(Δ/σ)max = 0.011
896 parametersΔρmax = 0.33 e Å3
180 restraintsΔρmin = 0.31 e Å3
Crystal data top
C16H18N4O4γ = 95.245 (2)°
Mr = 330.34V = 1621.7 (4) Å3
Triclinic, P1Z = 4
a = 9.3587 (12) ÅMo Kα radiation
b = 10.3445 (13) ŵ = 0.10 mm1
c = 16.925 (2) ÅT = 100 K
α = 92.079 (2)°0.25 × 0.20 × 0.04 mm
β = 95.775 (2)°
Data collection top
Bruker SMART APEX
diffractometer
6059 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
5788 reflections with I > \2s(I)
Tmin = 0.832, Tmax = 0.998Rint = 0.025
8913 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.064180 restraints
wR(F2) = 0.150H-atom parameters constrained
S = 1.13Δρmax = 0.33 e Å3
6059 reflectionsΔρmin = 0.31 e Å3
896 parameters
Special details top

Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

5.0129 (. 0164) x − 2.9332 (. 0218) y + 12.9110 (. 0229) z = 5.3195 (. 0225)

*. 0201 (. 0033) N1A * -.0142 (. 0032) C2A * -.0051 (. 0034) N3A *. 0182 (. 0039) C4A * -.0129 (. 0042) C5A * -.0061 (. 0037) C6A

Rms deviation of fitted atoms =. 0139

5.5015 (. 0229) x + 3.7261 (. 0278) y + 10.3521 (. 0361) z = 6.8078 (. 0194)

Angle to previous plane (with approximate e.s.d.) = 38.76 (. 23)

*. 0008 (. 0043) C12A *. 0056 (. 0042) C13A * -.0060 (. 0044) C14A * -.0001 (. 0052) C15A *. 0066 (. 0060) C16A * -.0070 (. 0054) C17A

Rms deviation of fitted atoms =. 0052

3.4151 (. 0177) x + 4.2599 (. 0189) y + 12.7715 (. 0223) z = 5.6594 (. 0040)

Angle to previous plane (with approximate e.s.d.) = 14.73 (. 35)

* -.0246 (. 0031) N1B *. 0347 (. 0030) C2B * -.0223 (. 0034) N3B * -.0011 (. 0037) C4B *. 0123 (. 0037) C5B *. 0010 (. 0034) C6B

Rms deviation of fitted atoms =. 0202

2.4451 (. 0218) x − 5.5455 (. 0206) y + 13.6929 (. 0227) z = 5.9373 (. 0214)

Angle to previous plane (with approximate e.s.d.) = 57.83 (. 15)

*. 0121 (. 0038) C12B * -.0070 (. 0039) C13B * -.0015 (. 0042) C14B *. 0050 (. 0043) C15B *. 0001 (. 0045) C16B * -.0087 (. 0043) C17B

Rms deviation of fitted atoms =. 0070

7.8870 (. 0111) x + 4.6700 (. 0202) y -. 3288 (. 0341) z = 4.7114 (. 0303)

Angle to previous plane (with approximate e.s.d.) = 88.80 (. 17)

*. 0090 (. 0033) N1C * -.0262 (. 0031) C2C *. 0240 (. 0032) N3C * -.0036 (. 0034) C4C * -.0147 (. 0039) C5C *. 0114 (. 0038) C6C

Rms deviation of fitted atoms =. 0168

6.6549 (. 0188) x + 3.2685 (. 0367) y + 8.4166 (. 0439) z = 6.9808 (. 0357)

Angle to previous plane (with approximate e.s.d.) = 31.19 (. 28)

*. 0000 (. 0003) C12C *. 0000 (. 0003) C13C *. 0000 (. 0003) C14C *. 0000 (. 0001) C15C *. 0000 (. 0001) C16C *. 0000 (. 0001) C17C

Rms deviation of fitted atoms =. 0000

8.5682 (. 0083) x − 4.7947 (. 0200) y +. 8846 (. 0349) z =. 9288 (. 0203)

Angle to previous plane (with approximate e.s.d.) = 54.52 (. 19)

* -.0032 (. 0033) N1D *. 0193 (. 0032) C2D * -.0200 (. 0034) N3D *. 0040 (. 0036) C4D *. 0127 (. 0041) C5D * -.0127 (. 0039) C6D

Rms deviation of fitted atoms =. 0137

8.0948 (. 0120) x − 1.6207 (. 0266) y + 6.9268 (. 0388) z = 8.9597 (. 0201)

Angle to previous plane (with approximate e.s.d.) = 27.75 (. 20)

* -.0065 (. 0040) C12D *. 0029 (. 0041) C13D *. 0020 (. 0045) C14D * -.0032 (. 0045) C15D * -.0005 (. 0046) C16D *. 0054 (. 0046) C17D

Rms deviation of fitted atoms =. 0040

—- Hydrogen bond rings (N3···O18 and N4.·O19; 8 membered ring) —-

Molecules A···D[x, y + 1, z] 4.1298 (. 0418) x +. 7475 (. 0141) y + 14.1362 (. 0423) z = 7.6737 (. 0117)

*. 1982 (. 0032) N3A *. 3917 (. 0045) H3A * -.2569 (. 0040) C4A * -.3639 (. 0043) N4A * -.1395 (. 0030) H4AA *. 1275 (. 0035) O18D *. 2335 (. 0040) C18D * -.1906 (. 0033) O19D

Rms deviation of fitted atoms =. 2544

Molecules B···C[x + 1, y, z − 1] 6.5453 (. 0105) x + 5.0240 (. 0217) y + 6.0219 (. 0123) z = 6.5201 (. 0047)

* -.1711 (. 0018) N3B *. 2112 (. 0017) H3B * -.4253 (. 0054) C4B * -.0363 (. 0024) N4B *. 3730 (. 0025) H4AB * -.0689 (. 0036) O18C *. 0894 (. 0040) C18C *. 0280 (. 0036) O19C

Rms deviation of fitted atoms =. 2260

Molecules C···B 7.9675 (. 0085) x + 4.1141 (. 0197) y + 1.8349 (. 0235) z = 6.0160 (. 0134)

*. 1336 (. 0021) N3C *. 0998 (. 0022) H3C *. 0549 (. 0043) C4C * -.1117 (. 0021) N4C * -.1705 (. 0021) H4AC *. 2418 (. 0034) O18B *. 0558 (. 0033) C18B * -.3037 (. 0036) O19B

Rms deviation of fitted atoms =. 1681

Molecules D···A[x − 1, y − 1, z + 1] 8.2484 (. 0024) x − 4.5493 (. 0164) y + 3.9099 (. 0201) z = 3.0131 (. 0158)

* -.1346 (. 0020) N3D * -.0343 (. 0022) H3D * -.1213 (. 0049) C4D *. 0789 (. 0021) N4D *. 2047 (. 0019) H4AD * -.2068 (. 0034) O18A * -.0042 (. 0040) C18A *. 2176 (. 0036) O19A

Rms deviation of fitted atoms =. 1467

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*/UeqOcc. (<1)
N1A1.0384 (5)0.8402 (4)0.2013 (2)0.0172 (9)
C2A0.9431 (5)0.8927 (5)0.2476 (3)0.0152 (10)
O2A0.9535 (4)1.0074 (3)0.2672 (2)0.0182 (8)
N3A0.8368 (4)0.8058 (4)0.2698 (2)0.0169 (9)
H3A0.77500.83630.29990.020*
C4A0.8184 (6)0.6781 (6)0.2497 (3)0.0243 (12)
N4A0.7133 (6)0.6065 (5)0.2766 (4)0.0415 (15)
H4AA0.65580.64210.30740.050*
H4BA0.69990.52270.26400.050*
C5A0.9161 (6)0.6295 (6)0.1983 (3)0.0268 (13)
H5A0.90590.54080.18020.032*
C6A1.0209 (6)0.7116 (5)0.1768 (3)0.0198 (11)
H6A1.08650.68000.14310.024*
C7A1.1660 (5)0.9264 (5)0.1843 (3)0.0170 (11)
H7AA1.23810.87290.16410.020*
H7BA1.21040.97250.23430.020*
C8A1.1266 (5)1.0265 (5)0.1230 (3)0.0168 (11)
H8AA1.04891.07570.14090.020*
H8BA1.21181.08890.11840.020*
C9A1.0763 (5)0.9587 (5)0.0423 (3)0.0169 (11)
O9A1.1247 (5)0.8564 (4)0.0233 (2)0.0315 (10)
N10A0.9817 (5)1.0149 (4)0.0043 (2)0.0161 (9)
H10A0.95231.08880.01180.019*
C10A0.9253 (5)0.9575 (5)0.0813 (3)0.0165 (10)
H10AA0.94430.86390.08190.020*
C11A0.7610 (6)0.9624 (6)0.0949 (4)0.0280 (13)
H11AA0.74001.05410.09900.034*
H11BA0.72430.91590.14610.034*
C12A0.6817 (6)0.9028 (6)0.0295 (4)0.0262 (13)
C13A0.7094 (6)0.7842 (6)0.0011 (3)0.0274 (13)
H13A0.78190.73900.02220.033*
C14A0.6341 (6)0.7279 (6)0.0580 (4)0.0325 (14)
H14A0.65490.64490.07570.039*
C15A0.5307 (7)0.7912 (7)0.0908 (4)0.0422 (17)
H15A0.47980.75350.13140.051*
C16A0.5024 (8)0.9103 (8)0.0636 (6)0.056 (2)
H16A0.43170.95610.08610.067*
C17A0.5758 (7)0.9652 (7)0.0035 (5)0.0424 (17)
H17A0.55281.04700.01510.051*
C18A0.9986 (6)1.0204 (5)0.1499 (3)0.0179 (11)
O18A1.0375 (4)1.1389 (4)0.1458 (2)0.0217 (8)
O19A1.0101 (5)0.9427 (4)0.2077 (2)0.0297 (10)
N1B0.3415 (4)0.3189 (4)0.2435 (2)0.0154 (9)
C2B0.4484 (5)0.3754 (5)0.2007 (3)0.0138 (10)
O2B0.4418 (4)0.4833 (3)0.1755 (2)0.0162 (7)
N3B0.5623 (5)0.3037 (4)0.1897 (3)0.0201 (10)
H3B0.62700.33280.15870.024*
C4B0.5777 (6)0.1910 (6)0.2249 (3)0.0242 (12)
N4B0.6936 (6)0.1314 (5)0.2131 (3)0.0350 (12)
H4AB0.75720.16600.18310.042*
H4BB0.70710.05730.23530.042*
C5B0.4716 (6)0.1388 (5)0.2717 (3)0.0214 (11)
H5B0.48150.05910.29690.026*
C6B0.3573 (6)0.2046 (5)0.2794 (3)0.0192 (11)
H6B0.28510.17090.31080.023*
C7B0.2157 (5)0.3919 (5)0.2538 (3)0.0162 (10)
H7AB0.13500.33130.26780.019*
H7BB0.18440.43010.20290.019*
C8B0.2491 (6)0.4994 (5)0.3180 (3)0.0194 (11)
H8AB0.16340.54820.32100.023*
H8BB0.32930.56060.30390.023*
C9B0.2911 (5)0.4455 (5)0.3991 (3)0.0130 (10)
O9B0.2369 (4)0.3391 (4)0.4158 (2)0.0188 (8)
N10B0.3856 (5)0.5215 (4)0.4480 (2)0.0153 (9)
H10B0.42020.59760.43290.018*
C10B0.4321 (5)0.4786 (5)0.5268 (3)0.0159 (10)
H10AB0.41550.38170.52620.019*
C11B0.5926 (6)0.5187 (5)0.5485 (3)0.0194 (11)
H11AB0.60950.61440.54630.023*
H11BB0.61890.49610.60410.023*
C12B0.6926 (6)0.4571 (5)0.4960 (3)0.0173 (11)
C13B0.6526 (6)0.3390 (5)0.4538 (3)0.0219 (11)
H13B0.55720.29860.45330.026*
C14B0.7533 (6)0.2794 (5)0.4122 (3)0.0237 (12)
H14B0.72630.19830.38410.028*
C15B0.8908 (7)0.3387 (6)0.4121 (4)0.0298 (14)
H15B0.95910.29830.38410.036*
C16B0.9295 (6)0.4567 (6)0.4526 (4)0.0317 (14)
H16B1.02460.49750.45230.038*
C17B0.8305 (6)0.5161 (6)0.4937 (4)0.0263 (12)
H17B0.85780.59820.52060.032*
C18B0.3487 (5)0.5365 (5)0.5920 (3)0.0139 (10)
O18B0.3147 (4)0.6492 (3)0.5882 (2)0.0188 (8)
O19B0.3291 (4)0.4620 (3)0.6484 (2)0.0222 (8)
N1C0.3184 (5)0.5382 (4)0.9240 (2)0.0162 (9)
C2C0.3397 (5)0.4894 (5)0.8497 (3)0.0130 (10)
O2C0.3885 (4)0.3859 (3)0.8393 (2)0.0188 (8)
N3C0.2989 (5)0.5647 (4)0.7876 (2)0.0143 (8)
H3C0.31840.54000.73980.017*
C4C0.2312 (5)0.6736 (5)0.7944 (3)0.0157 (10)
N4C0.1935 (5)0.7348 (4)0.7302 (3)0.0211 (10)
H4AC0.21240.70470.68340.025*
H4BC0.14930.80590.73380.025*
C5C0.2072 (7)0.7172 (6)0.8716 (3)0.0253 (12)
H5C0.15930.79300.87920.030*
C6C0.2528 (6)0.6500 (5)0.9336 (3)0.0191 (11)
H6C0.23950.68060.98570.023*
C7C0.3619 (5)0.4616 (5)0.9936 (3)0.0168 (11)
H7AC0.37290.51861.04250.020*
H7BC0.45630.42870.98720.020*
C8C0.2511 (5)0.3484 (5)1.0018 (3)0.0152 (10)
H8AC0.28440.29741.04730.018*
H8BC0.24100.29090.95320.018*
C9C0.1058 (5)0.3947 (4)1.0147 (3)0.0121 (10)
O9C0.0954 (4)0.4761 (4)1.0693 (2)0.0184 (8)
N10C0.0053 (4)0.3480 (4)0.9647 (2)0.0143 (9)
H10C0.00620.29320.92540.017*
C10C0.1470 (5)0.3881 (5)0.9751 (3)0.0159 (10)
H10AC0.13740.48460.98450.019*
C11C0.2514 (5)0.3537 (5)0.8995 (3)0.0186 (11)
H11AC0.24580.26170.88280.022*
H11BC0.35120.36290.91180.022*
C12C0.2186 (5)0.4380 (4)0.8322 (2)0.0169 (12)0.96 (3)
C13C0.1294 (5)0.3994 (5)0.7766 (3)0.0330 (16)0.96 (3)
H13AC0.09250.31700.77950.040*0.96 (3)
C14C0.0941 (8)0.4815 (6)0.7168 (3)0.046 (2)0.96 (3)
H14AC0.03310.45520.67880.056*0.96 (3)
C15C0.1480 (11)0.6022 (5)0.7126 (3)0.052 (3)0.96 (3)
H15AC0.12390.65830.67180.062*0.96 (3)
C16C0.2372 (11)0.6407 (4)0.7682 (3)0.053 (3)0.96 (3)
H16AC0.27410.72320.76530.063*0.96 (3)
C17C0.2725 (8)0.5586 (4)0.8279 (3)0.0395 (19)0.96 (3)
H17AC0.33350.58500.86590.047*0.96 (3)
C12'C0.238 (9)0.438 (5)0.830 (3)0.034 (12)0.04 (3)
C13'C0.152 (13)0.406 (11)0.771 (4)0.032 (11)0.04 (3)
H13'C0.09970.33150.77580.038*0.04 (3)
C14'C0.14 (2)0.483 (14)0.706 (6)0.039 (12)0.04 (3)
H14'C0.08250.46100.66600.046*0.04 (3)
C15'C0.22 (2)0.592 (13)0.700 (6)0.052 (13)0.04 (3)
H15'C0.21050.64470.65500.063*0.04 (3)
C16'C0.30 (2)0.624 (11)0.758 (7)0.047 (13)0.04 (3)
H16'C0.35570.69870.75360.057*0.04 (3)
C17'C0.314 (16)0.547 (8)0.823 (5)0.037 (12)0.04 (3)
H17'C0.37290.56920.86340.045*0.04 (3)
C18C0.2051 (6)0.3269 (5)1.0478 (3)0.0181 (11)
O18C0.3036 (4)0.3912 (4)1.0749 (2)0.0225 (8)
O19C0.1637 (4)0.2280 (4)1.0751 (2)0.0218 (8)
N1D0.0463 (4)0.0146 (4)0.5187 (2)0.0141 (9)
C2D0.0184 (5)0.0554 (4)0.5932 (3)0.0111 (9)
O2D0.0335 (4)0.1638 (3)0.6022 (2)0.0189 (8)
N3D0.0577 (5)0.0344 (4)0.6544 (2)0.0150 (9)
H3D0.03560.01300.70190.018*
C4D0.1274 (6)0.1528 (5)0.6486 (3)0.0193 (11)
N4D0.1630 (5)0.2280 (5)0.7123 (3)0.0267 (11)
H4AD0.14150.20130.75880.032*
H4BD0.20860.30550.70880.032*
C5D0.1572 (7)0.1899 (5)0.5711 (4)0.0277 (13)
H5D0.20670.27200.56340.033*
C6D0.1138 (6)0.1064 (5)0.5098 (3)0.0219 (12)
H6D0.13040.13180.45790.026*
C7D0.0088 (5)0.1060 (5)0.4507 (3)0.0155 (10)
H7AD0.00150.05720.40150.019*
H7BD0.08530.15510.45610.019*
C8D0.1234 (5)0.2016 (5)0.4437 (3)0.0135 (10)
H8AD0.13750.24800.49360.016*
H8BD0.09070.26680.39980.016*
C9D0.2650 (5)0.1283 (5)0.4276 (3)0.0148 (10)
O9D0.2714 (4)0.0574 (4)0.3716 (2)0.0228 (8)
N10D0.3801 (4)0.1442 (4)0.4784 (2)0.0135 (8)
H10D0.37140.19330.51930.016*
C10D0.5187 (5)0.0803 (5)0.4656 (3)0.0171 (11)
H10AD0.50580.01120.45130.020*
C11D0.6272 (6)0.0772 (6)0.5404 (3)0.0209 (11)
H11AD0.64220.16760.55390.025*
H11BD0.72090.03430.52820.025*
C12D0.5809 (5)0.0073 (5)0.6120 (3)0.0192 (11)
C13D0.5184 (6)0.0759 (6)0.6703 (4)0.0270 (13)
H13D0.50500.16810.66540.032*
C14D0.4752 (7)0.0114 (7)0.7358 (4)0.0344 (15)
H14D0.43210.05990.77530.041*
C15D0.4938 (7)0.1205 (7)0.7442 (4)0.0387 (16)
H15D0.46330.16390.78910.046*
C16D0.5567 (8)0.1905 (6)0.6874 (4)0.0427 (18)
H16D0.57020.28260.69290.051*
C17D0.6004 (8)0.1264 (6)0.6221 (4)0.0377 (16)
H17D0.64500.17560.58340.045*
C18D0.5841 (5)0.1494 (5)0.3966 (3)0.0159 (10)
O18D0.6704 (4)0.0788 (4)0.3602 (2)0.0210 (8)
O19D0.5520 (4)0.2677 (4)0.3822 (2)0.0240 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.018 (2)0.024 (2)0.010 (2)0.0037 (18)0.0038 (17)0.0016 (17)
C2A0.015 (2)0.023 (3)0.008 (2)0.001 (2)0.0017 (19)0.003 (2)
O2A0.0228 (19)0.019 (2)0.0139 (18)0.0030 (15)0.0061 (15)0.0008 (14)
N3A0.012 (2)0.027 (2)0.012 (2)0.0014 (17)0.0039 (16)0.0032 (18)
C4A0.019 (3)0.030 (3)0.023 (3)0.003 (2)0.005 (2)0.011 (2)
N4A0.036 (3)0.026 (3)0.061 (4)0.016 (2)0.027 (3)0.022 (3)
C5A0.033 (3)0.020 (3)0.026 (3)0.003 (2)0.006 (2)0.018 (2)
C6A0.019 (3)0.025 (3)0.014 (2)0.002 (2)0.001 (2)0.010 (2)
C7A0.018 (3)0.023 (3)0.010 (2)0.002 (2)0.0024 (19)0.001 (2)
C8A0.016 (2)0.024 (3)0.011 (2)0.002 (2)0.006 (2)0.002 (2)
C9A0.017 (3)0.024 (3)0.012 (2)0.003 (2)0.010 (2)0.002 (2)
O9A0.043 (3)0.039 (2)0.016 (2)0.029 (2)0.0041 (18)0.0064 (17)
N10A0.021 (2)0.017 (2)0.013 (2)0.0079 (17)0.0057 (17)0.0019 (16)
C10A0.021 (3)0.014 (2)0.014 (3)0.003 (2)0.001 (2)0.0031 (19)
C11A0.024 (3)0.029 (3)0.030 (3)0.006 (2)0.007 (2)0.004 (2)
C12A0.016 (3)0.030 (3)0.031 (3)0.002 (2)0.003 (2)0.009 (2)
C13A0.028 (3)0.029 (3)0.025 (3)0.003 (2)0.003 (2)0.005 (2)
C14A0.025 (3)0.033 (3)0.037 (4)0.007 (3)0.001 (3)0.002 (3)
C15A0.027 (3)0.048 (4)0.051 (4)0.011 (3)0.015 (3)0.009 (3)
C16A0.041 (4)0.049 (5)0.085 (6)0.006 (3)0.040 (4)0.002 (4)
C17A0.033 (4)0.031 (4)0.065 (5)0.011 (3)0.012 (3)0.003 (3)
C18A0.025 (3)0.020 (3)0.009 (2)0.011 (2)0.002 (2)0.003 (2)
O18A0.030 (2)0.024 (2)0.0121 (18)0.0036 (16)0.0068 (16)0.0050 (15)
O19A0.059 (3)0.019 (2)0.0132 (19)0.0099 (19)0.0095 (18)0.0009 (15)
N1B0.016 (2)0.022 (2)0.0071 (19)0.0002 (17)0.0029 (16)0.0032 (16)
C2B0.013 (2)0.023 (3)0.005 (2)0.0026 (19)0.0002 (18)0.0036 (19)
O2B0.0204 (18)0.0188 (18)0.0104 (17)0.0021 (14)0.0055 (14)0.0025 (14)
N3B0.020 (2)0.028 (2)0.015 (2)0.0044 (19)0.0102 (18)0.0053 (18)
C4B0.024 (3)0.027 (3)0.022 (3)0.008 (2)0.001 (2)0.000 (2)
N4B0.042 (3)0.034 (3)0.034 (3)0.020 (2)0.010 (2)0.012 (2)
C5B0.036 (3)0.013 (2)0.017 (3)0.006 (2)0.003 (2)0.005 (2)
C6B0.028 (3)0.018 (3)0.011 (2)0.000 (2)0.002 (2)0.0022 (19)
C7B0.011 (2)0.030 (3)0.007 (2)0.000 (2)0.0024 (18)0.002 (2)
C8B0.017 (3)0.030 (3)0.013 (3)0.008 (2)0.004 (2)0.005 (2)
C9B0.015 (2)0.015 (3)0.010 (2)0.0026 (19)0.0073 (19)0.0017 (19)
O9B0.0190 (18)0.025 (2)0.0107 (17)0.0058 (15)0.0028 (14)0.0010 (14)
N10B0.020 (2)0.017 (2)0.009 (2)0.0011 (17)0.0053 (17)0.0009 (16)
C10B0.019 (3)0.024 (3)0.005 (2)0.000 (2)0.0000 (19)0.0037 (19)
C11B0.022 (3)0.019 (3)0.016 (3)0.002 (2)0.001 (2)0.002 (2)
C12B0.019 (3)0.024 (3)0.010 (2)0.002 (2)0.003 (2)0.005 (2)
C13B0.020 (3)0.025 (3)0.020 (3)0.001 (2)0.005 (2)0.002 (2)
C14B0.024 (3)0.024 (3)0.023 (3)0.001 (2)0.002 (2)0.009 (2)
C15B0.034 (3)0.033 (3)0.025 (3)0.010 (3)0.009 (3)0.001 (3)
C16B0.016 (3)0.037 (4)0.044 (4)0.001 (2)0.011 (3)0.006 (3)
C17B0.031 (3)0.022 (3)0.026 (3)0.001 (2)0.009 (2)0.002 (2)
C18B0.014 (2)0.020 (3)0.007 (2)0.002 (2)0.0004 (18)0.0023 (19)
O18B0.024 (2)0.023 (2)0.0106 (17)0.0048 (15)0.0063 (14)0.0033 (14)
O19B0.040 (2)0.0153 (18)0.0113 (18)0.0016 (16)0.0093 (16)0.0012 (14)
N1C0.021 (2)0.019 (2)0.009 (2)0.0033 (17)0.0020 (17)0.0009 (17)
C2C0.011 (2)0.018 (3)0.011 (2)0.0016 (19)0.0036 (19)0.0027 (19)
O2C0.025 (2)0.0187 (19)0.0141 (18)0.0070 (15)0.0067 (15)0.0010 (15)
N3C0.020 (2)0.017 (2)0.0064 (19)0.0032 (17)0.0044 (16)0.0023 (15)
C4C0.019 (2)0.016 (2)0.013 (2)0.004 (2)0.009 (2)0.0013 (19)
N4C0.028 (2)0.023 (2)0.016 (2)0.010 (2)0.0097 (19)0.0083 (19)
C5C0.040 (3)0.023 (3)0.016 (3)0.009 (2)0.014 (2)0.002 (2)
C6C0.026 (3)0.021 (3)0.012 (2)0.005 (2)0.009 (2)0.004 (2)
C7C0.015 (2)0.029 (3)0.007 (2)0.010 (2)0.0008 (19)0.000 (2)
C8C0.018 (3)0.013 (2)0.016 (2)0.0053 (19)0.003 (2)0.0045 (19)
C9C0.015 (2)0.011 (2)0.011 (2)0.0006 (18)0.0022 (19)0.0056 (18)
O9C0.0208 (19)0.025 (2)0.0089 (17)0.0024 (15)0.0019 (14)0.0037 (14)
N10C0.015 (2)0.018 (2)0.0096 (19)0.0002 (17)0.0039 (16)0.0052 (16)
C10C0.014 (2)0.018 (3)0.017 (3)0.004 (2)0.005 (2)0.000 (2)
C11C0.013 (2)0.028 (3)0.014 (2)0.003 (2)0.000 (2)0.003 (2)
C12C0.014 (3)0.023 (3)0.012 (3)0.005 (2)0.002 (2)0.000 (2)
C13C0.019 (3)0.055 (4)0.025 (3)0.002 (3)0.002 (3)0.014 (3)
C14C0.027 (4)0.082 (6)0.028 (4)0.008 (4)0.002 (3)0.023 (4)
C15C0.050 (6)0.064 (5)0.029 (4)0.042 (4)0.023 (4)0.034 (4)
C16C0.089 (8)0.026 (4)0.034 (4)0.010 (4)0.033 (5)0.010 (3)
C17C0.052 (5)0.034 (4)0.027 (4)0.000 (3)0.012 (3)0.003 (3)
C12'C0.03 (2)0.04 (2)0.02 (2)0.00 (2)0.001 (19)0.00 (2)
C13'C0.017 (19)0.05 (2)0.021 (19)0.002 (19)0.007 (19)0.011 (19)
C14'C0.03 (2)0.06 (2)0.025 (19)0.02 (2)0.000 (19)0.024 (19)
C15'C0.06 (2)0.05 (2)0.03 (2)0.02 (2)0.01 (2)0.01 (2)
C16'C0.06 (2)0.04 (2)0.03 (2)0.02 (2)0.02 (2)0.01 (2)
C17'C0.05 (2)0.03 (2)0.02 (2)0.008 (19)0.012 (19)0.006 (19)
C18C0.017 (3)0.024 (3)0.014 (2)0.006 (2)0.003 (2)0.003 (2)
O18C0.023 (2)0.030 (2)0.0193 (19)0.0126 (16)0.0131 (16)0.0049 (16)
O19C0.026 (2)0.024 (2)0.0185 (19)0.0093 (16)0.0102 (16)0.0057 (16)
N1D0.012 (2)0.022 (2)0.010 (2)0.0062 (17)0.0073 (16)0.0007 (16)
C2D0.014 (2)0.010 (2)0.010 (2)0.0020 (18)0.0038 (18)0.0060 (18)
O2D0.0234 (19)0.0184 (19)0.0152 (18)0.0030 (15)0.0088 (15)0.0002 (14)
N3D0.016 (2)0.021 (2)0.008 (2)0.0014 (17)0.0048 (16)0.0006 (16)
C4D0.018 (3)0.022 (3)0.020 (3)0.004 (2)0.008 (2)0.006 (2)
N4D0.028 (3)0.023 (2)0.029 (3)0.002 (2)0.012 (2)0.009 (2)
C5D0.034 (3)0.016 (3)0.035 (3)0.006 (2)0.024 (3)0.001 (2)
C6D0.029 (3)0.019 (3)0.021 (3)0.004 (2)0.017 (2)0.005 (2)
C7D0.012 (2)0.029 (3)0.006 (2)0.002 (2)0.0029 (18)0.000 (2)
C8D0.011 (2)0.019 (3)0.011 (2)0.0021 (19)0.0063 (19)0.0022 (19)
C9D0.019 (3)0.016 (2)0.011 (2)0.004 (2)0.007 (2)0.0041 (19)
O9D0.022 (2)0.032 (2)0.0145 (18)0.0004 (16)0.0035 (15)0.0088 (16)
N10D0.014 (2)0.022 (2)0.0049 (19)0.0027 (17)0.0022 (16)0.0043 (16)
C10D0.012 (2)0.023 (3)0.017 (3)0.001 (2)0.005 (2)0.006 (2)
C11D0.014 (3)0.028 (3)0.021 (3)0.004 (2)0.001 (2)0.000 (2)
C12D0.008 (2)0.025 (3)0.024 (3)0.001 (2)0.003 (2)0.003 (2)
C13D0.026 (3)0.028 (3)0.026 (3)0.002 (2)0.006 (2)0.009 (2)
C14D0.030 (3)0.043 (4)0.031 (3)0.002 (3)0.008 (3)0.005 (3)
C15D0.028 (3)0.055 (4)0.031 (3)0.014 (3)0.009 (3)0.018 (3)
C16D0.057 (4)0.025 (3)0.042 (4)0.015 (3)0.017 (3)0.015 (3)
C17D0.055 (4)0.029 (3)0.027 (3)0.001 (3)0.005 (3)0.002 (3)
C18D0.008 (2)0.023 (3)0.017 (3)0.006 (2)0.0000 (19)0.004 (2)
O18D0.0168 (18)0.0207 (19)0.027 (2)0.0010 (15)0.0124 (16)0.0019 (16)
O19D0.029 (2)0.020 (2)0.024 (2)0.0048 (16)0.0150 (17)0.0009 (16)
Geometric parameters (Å, º) top
N1A—C6A1.369 (7)N3C—H3C0.8800
N1A—C2A1.380 (7)C4C—N4C1.312 (7)
N1A—C7A1.481 (7)C4C—C5C1.412 (7)
C2A—O2A1.213 (6)N4C—H4AC0.8800
C2A—N3A1.370 (6)N4C—H4BC0.8800
N3A—C4A1.343 (7)C5C—C6C1.335 (8)
N3A—H3A0.8800C5C—H5C0.9500
C4A—N4A1.306 (8)C6C—H6C0.9500
C4A—C5A1.434 (8)C7C—C8C1.512 (7)
N4A—H4AA0.8800C7C—H7AC0.9900
N4A—H4BA0.8800C7C—H7BC0.9900
C5A—C6A1.327 (8)C8C—C9C1.515 (7)
C5A—H5A0.9500C8C—H8AC0.9900
C6A—H6A0.9500C8C—H8BC0.9900
C7A—C8A1.535 (7)C9C—O9C1.245 (6)
C7A—H7AA0.9900C9C—N10C1.316 (6)
C7A—H7BA0.9900N10C—C10C1.450 (6)
C8A—C9A1.523 (7)N10C—H10C0.8800
C8A—H8AA0.9900C10C—C18C1.529 (7)
C8A—H8BA0.9900C10C—C11C1.539 (7)
C9A—O9A1.233 (6)C10C—H10AC1.0000
C9A—N10A1.316 (7)C11C—C12C1.500 (6)
N10A—C10A1.441 (6)C11C—C12'C1.50
N10A—H10A0.8800C11C—H11AC0.9900
C10A—C11A1.537 (8)C11C—H11BC0.9900
C10A—C18A1.541 (7)C12C—C13C1.3900
C10A—H10AA1.0000C12C—C17C1.3900
C11A—C12A1.512 (9)C13C—C14C1.3900
C11A—H11AA0.9900C13C—H13AC0.9500
C11A—H11BA0.9900C14C—C15C1.3900
C12A—C13A1.371 (9)C14C—H14AC0.9500
C12A—C17A1.383 (9)C15C—C16C1.3900
C13A—C14A1.394 (9)C15C—H15AC0.9500
C13A—H13A0.9500C16C—C17C1.3900
C14A—C15A1.367 (10)C16C—H16AC0.9500
C14A—H14A0.9500C17C—H17AC0.9500
C15A—C16A1.369 (11)C12'C—C13'C1.39
C15A—H15A0.9500C12'C—C17'C1.39
C16A—C17A1.393 (11)C13'C—C14'C1.39
C16A—H16A0.9500C13'C—H13'C0.95
C17A—H17A0.9500C14'C—C15'C1.41
C18A—O18A1.244 (6)C14'C—H14'C0.95
C18A—O19A1.264 (6)C15'C—C16'C1.34
N1B—C6B1.361 (7)C15'C—H15'C0.95
N1B—C2B1.392 (6)C16'C—C17'C1.39
N1B—C7B1.477 (7)C16'C—H16'C0.97
C2B—O2B1.214 (6)C17'C—H17'C0.95
C2B—N3B1.377 (7)C18C—O19C1.217 (6)
N3B—C4B1.340 (7)C18C—O18C1.295 (6)
N3B—H3B0.8800N1D—C6D1.370 (7)
C4B—N4B1.325 (8)N1D—C2D1.386 (6)
C4B—C5B1.413 (8)N1D—C7D1.455 (6)
N4B—H4AB0.8800C2D—O2D1.202 (6)
N4B—H4BB0.8800C2D—N3D1.365 (6)
C5B—C6B1.335 (8)N3D—C4D1.346 (7)
C5B—H5B0.9500N3D—H3D0.8800
C6B—H6B0.9500C4D—N4D1.302 (7)
C7B—C8B1.514 (7)C4D—C5D1.427 (8)
C7B—H7AB0.9900N4D—H4AD0.8800
C7B—H7BB0.9900N4D—H4BD0.8800
C8B—C9B1.529 (7)C5D—C6D1.331 (8)
C8B—H8AB0.9900C5D—H5D0.9500
C8B—H8BB0.9900C6D—H6D0.9500
C9B—O9B1.224 (6)C7D—C8D1.535 (7)
C9B—N10B1.328 (6)C7D—H7AD0.9900
N10B—C10B1.458 (6)C7D—H7BD0.9900
N10B—H10B0.8800C8D—C9D1.520 (7)
C10B—C11B1.526 (7)C8D—H8AD0.9900
C10B—C18B1.549 (7)C8D—H8BD0.9900
C10B—H10AB1.0000C9D—O9D1.222 (6)
C11B—C12B1.519 (7)C9D—N10D1.336 (6)
C11B—H11AB0.9900N10D—C10D1.442 (6)
C11B—H11BB0.9900N10D—H10D0.8800
C12B—C17B1.381 (8)C10D—C11D1.539 (7)
C12B—C13B1.394 (8)C10D—C18D1.552 (7)
C13B—C14B1.404 (8)C10D—H10AD1.0000
C13B—H13B0.9500C11D—C12D1.510 (8)
C14B—C15B1.374 (9)C11D—H11AD0.9900
C14B—H14B0.9500C11D—H11BD0.9900
C15B—C16B1.378 (9)C12D—C17D1.381 (8)
C15B—H15B0.9500C12D—C13D1.382 (8)
C16B—C17B1.387 (8)C13D—C14D1.388 (8)
C16B—H16B0.9500C13D—H13D0.9500
C17B—H17B0.9500C14D—C15D1.360 (10)
C18B—O18B1.238 (6)C14D—H14D0.9500
C18B—O19B1.265 (6)C15D—C16D1.372 (11)
N1C—C6C1.370 (7)C15D—H15D0.9500
N1C—C2C1.377 (6)C16D—C17D1.384 (10)
N1C—C7C1.487 (6)C16D—H16D0.9500
C2C—O2C1.216 (6)C17D—H17D0.9500
C2C—N3C1.375 (6)C18D—O19D1.242 (6)
N3C—C4C1.349 (6)C18D—O18D1.262 (6)
C6A—N1A—C2A121.2 (4)N3C—C4C—C5C117.5 (5)
C6A—N1A—C7A121.5 (4)C4C—N4C—H4AC120.0
C2A—N1A—C7A117.1 (4)C4C—N4C—H4BC120.0
O2A—C2A—N3A122.8 (5)H4AC—N4C—H4BC120.0
O2A—C2A—N1A122.2 (5)C6C—C5C—C4C119.0 (5)
N3A—C2A—N1A115.0 (4)C6C—C5C—H5C120.5
C4A—N3A—C2A125.8 (5)C4C—C5C—H5C120.5
C4A—N3A—H3A117.1C5C—C6C—N1C121.7 (5)
C2A—N3A—H3A117.1C5C—C6C—H6C119.2
N4A—C4A—N3A118.9 (5)N1C—C6C—H6C119.2
N4A—C4A—C5A124.1 (5)N1C—C7C—C8C111.1 (4)
N3A—C4A—C5A117.0 (5)N1C—C7C—H7AC109.4
C4A—N4A—H4AA120.0C8C—C7C—H7AC109.4
C4A—N4A—H4BA120.0N1C—C7C—H7BC109.4
H4AA—N4A—H4BA120.0C8C—C7C—H7BC109.4
C6A—C5A—C4A118.2 (5)H7AC—C7C—H7BC108.0
C6A—C5A—H5A120.9C7C—C8C—C9C111.2 (4)
C4A—C5A—H5A120.9C7C—C8C—H8AC109.4
C5A—C6A—N1A122.6 (5)C9C—C8C—H8AC109.4
C5A—C6A—H6A118.7C7C—C8C—H8BC109.4
N1A—C6A—H6A118.7C9C—C8C—H8BC109.4
N1A—C7A—C8A112.1 (4)H8AC—C8C—H8BC108.0
N1A—C7A—H7AA109.2O9C—C9C—N10C122.5 (5)
C8A—C7A—H7AA109.2O9C—C9C—C8C120.3 (4)
N1A—C7A—H7BA109.2N10C—C9C—C8C117.1 (4)
C8A—C7A—H7BA109.2C9C—N10C—C10C119.2 (4)
H7AA—C7A—H7BA107.9C9C—N10C—H10C120.4
C9A—C8A—C7A110.3 (4)C10C—N10C—H10C120.4
C9A—C8A—H8AA109.6N10C—C10C—C18C110.6 (4)
C7A—C8A—H8AA109.6N10C—C10C—C11C110.6 (4)
C9A—C8A—H8BA109.6C18C—C10C—C11C111.3 (4)
C7A—C8A—H8BA109.6N10C—C10C—H10AC108.1
H8AA—C8A—H8BA108.1C18C—C10C—H10AC108.1
O9A—C9A—N10A123.2 (5)C11C—C10C—H10AC108.1
O9A—C9A—C8A119.9 (5)C12C—C11C—C10C112.7 (4)
N10A—C9A—C8A116.9 (4)C12'C—C11C—C10C118 (3)
C9A—N10A—C10A121.2 (4)C12C—C11C—H11AC109.1
C9A—N10A—H10A119.4C12'C—C11C—H11AC110.0
C10A—N10A—H10A119.4C10C—C11C—H11AC109.1
N10A—C10A—C11A110.7 (4)C12C—C11C—H11BC109.1
N10A—C10A—C18A112.9 (4)C12'C—C11C—H11BC102.5
C11A—C10A—C18A110.3 (4)C10C—C11C—H11BC109.1
N10A—C10A—H10AA107.5H11AC—C11C—H11BC107.8
C11A—C10A—H10AA107.5C13C—C12C—C17C120.0
C18A—C10A—H10AA107.5C13C—C12C—C11C120.7 (3)
C12A—C11A—C10A113.3 (5)C17C—C12C—C11C119.2 (3)
C12A—C11A—H11AA108.9C12C—C13C—C14C120.0
C10A—C11A—H11AA108.9C12C—C13C—H13AC120.0
C12A—C11A—H11BA108.9C14C—C13C—H13AC120.0
C10A—C11A—H11BA108.9C13C—C14C—C15C120.0
H11AA—C11A—H11BA107.7C13C—C14C—H14AC120.0
C13A—C12A—C17A116.9 (6)C15C—C14C—H14AC120.0
C13A—C12A—C11A121.9 (5)C16C—C15C—C14C120.0
C17A—C12A—C11A121.2 (6)C16C—C15C—H15AC120.0
C12A—C13A—C14A121.9 (6)C14C—C15C—H15AC120.0
C12A—C13A—H13A119.0C15C—C16C—C17C120.0
C14A—C13A—H13A119.0C15C—C16C—H16AC120.0
C15A—C14A—C13A120.6 (6)C17C—C16C—H16AC120.0
C15A—C14A—H14A119.7C16C—C17C—C12C120.0
C13A—C14A—H14A119.7C16C—C17C—H17AC120.0
C14A—C15A—C16A118.3 (6)C12C—C17C—H17AC120.0
C14A—C15A—H15A120.8C13'C—C12'C—C17'C120.0
C16A—C15A—H15A120.8C13'C—C12'C—C11C120.1
C15A—C16A—C17A121.0 (7)C17'C—C12'C—C11C119.9
C15A—C16A—H16A119.5C12'C—C13'C—C14'C120.0
C17A—C16A—H16A119.5C12'C—C13'C—H13'C120.0
C12A—C17A—C16A121.3 (7)C14'C—C13'C—H13'C120.0
C12A—C17A—H17A119.4C15'C—C14'C—C13'C118.5
C16A—C17A—H17A119.4C15'C—C14'C—H14'C120.0
O18A—C18A—O19A125.8 (5)C13'C—C14'C—H14'C120.0
O18A—C18A—C10A119.9 (4)C14'C—C15'C—C16'C120.0
O19A—C18A—C10A114.2 (4)C14'C—C15'C—H15'C117.8
C6B—N1B—C2B121.0 (4)C16'C—C15'C—H15'C121.6
C6B—N1B—C7B121.1 (4)C17'C—C16'C—C15'C121.5
C2B—N1B—C7B117.7 (4)C17'C—C16'C—H16'C118.0
O2B—C2B—N3B122.0 (4)C15'C—C16'C—H16'C120.0
O2B—C2B—N1B121.3 (5)C16'C—C17'C—C12'C120.0
N3B—C2B—N1B116.7 (4)C16'C—C17'C—H17'C121.0
C4B—N3B—C2B121.9 (5)C12'C—C17'C—H17'C120.0
C4B—N3B—H3B119.0O19C—C18C—O18C125.1 (5)
C2B—N3B—H3B119.0O19C—C18C—C10C122.8 (5)
N4B—C4B—N3B117.6 (5)O18C—C18C—C10C112.1 (4)
N4B—C4B—C5B122.2 (5)C6D—N1D—C2D120.7 (4)
N3B—C4B—C5B120.2 (5)C6D—N1D—C7D120.8 (4)
C4B—N4B—H4AB120.0C2D—N1D—C7D118.3 (4)
C4B—N4B—H4BB120.0O2D—C2D—N3D123.3 (4)
H4AB—N4B—H4BB120.0O2D—C2D—N1D121.3 (4)
C6B—C5B—C4B118.1 (5)N3D—C2D—N1D115.3 (4)
C6B—C5B—H5B120.9C4D—N3D—C2D125.7 (4)
C4B—C5B—H5B120.9C4D—N3D—H3D117.1
C5B—C6B—N1B121.7 (5)C2D—N3D—H3D117.1
C5B—C6B—H6B119.2N4D—C4D—N3D119.7 (5)
N1B—C6B—H6B119.2N4D—C4D—C5D123.2 (5)
N1B—C7B—C8B112.2 (4)N3D—C4D—C5D117.1 (5)
N1B—C7B—H7AB109.2C4D—N4D—H4AD120.0
C8B—C7B—H7AB109.2C4D—N4D—H4BD120.0
N1B—C7B—H7BB109.2H4AD—N4D—H4BD120.0
C8B—C7B—H7BB109.2C6D—C5D—C4D118.4 (5)
H7AB—C7B—H7BB107.9C6D—C5D—H5D120.8
C7B—C8B—C9B111.5 (4)C4D—C5D—H5D120.8
C7B—C8B—H8AB109.3C5D—C6D—N1D122.6 (5)
C9B—C8B—H8AB109.3C5D—C6D—H6D118.7
C7B—C8B—H8BB109.3N1D—C6D—H6D118.7
C9B—C8B—H8BB109.3N1D—C7D—C8D111.8 (4)
H8AB—C8B—H8BB108.0N1D—C7D—H7AD109.2
O9B—C9B—N10B124.2 (5)C8D—C7D—H7AD109.2
O9B—C9B—C8B120.0 (4)N1D—C7D—H7BD109.2
N10B—C9B—C8B115.8 (4)C8D—C7D—H7BD109.2
C9B—N10B—C10B119.9 (4)H7AD—C7D—H7BD107.9
C9B—N10B—H10B120.0C9D—C8D—C7D109.7 (4)
C10B—N10B—H10B120.0C9D—C8D—H8AD109.7
N10B—C10B—C11B110.3 (4)C7D—C8D—H8AD109.7
N10B—C10B—C18B112.3 (4)C9D—C8D—H8BD109.7
C11B—C10B—C18B108.1 (4)C7D—C8D—H8BD109.7
N10B—C10B—H10AB108.7H8AD—C8D—H8BD108.2
C11B—C10B—H10AB108.7O9D—C9D—N10D122.4 (5)
C18B—C10B—H10AB108.7O9D—C9D—C8D121.2 (5)
C12B—C11B—C10B115.2 (4)N10D—C9D—C8D116.4 (4)
C12B—C11B—H11AB108.5C9D—N10D—C10D119.4 (4)
C10B—C11B—H11AB108.5C9D—N10D—H10D120.3
C12B—C11B—H11BB108.5C10D—N10D—H10D120.3
C10B—C11B—H11BB108.5N10D—C10D—C11D111.8 (4)
H11AB—C11B—H11BB107.5N10D—C10D—C18D111.2 (4)
C17B—C12B—C13B118.9 (5)C11D—C10D—C18D108.1 (4)
C17B—C12B—C11B118.9 (5)N10D—C10D—H10AD108.6
C13B—C12B—C11B122.1 (5)C11D—C10D—H10AD108.5
C12B—C13B—C14B120.1 (5)C18D—C10D—H10AD108.6
C12B—C13B—H13B119.9C12D—C11D—C10D114.1 (4)
C14B—C13B—H13B119.9C12D—C11D—H11AD108.7
C15B—C14B—C13B119.9 (5)C10D—C11D—H11AD108.7
C15B—C14B—H14B120.0C12D—C11D—H11BD108.7
C13B—C14B—H14B120.0C10D—C11D—H11BD108.7
C14B—C15B—C16B119.9 (6)H11AD—C11D—H11BD107.6
C14B—C15B—H15B120.0C17D—C12D—C13D117.8 (5)
C16B—C15B—H15B120.0C17D—C12D—C11D121.6 (5)
C15B—C16B—C17B120.4 (6)C13D—C12D—C11D120.7 (5)
C15B—C16B—H16B119.8C12D—C13D—C14D120.5 (6)
C17B—C16B—H16B119.8C12D—C13D—H13D119.7
C12B—C17B—C16B120.7 (5)C14D—C13D—H13D119.7
C12B—C17B—H17B119.7C15D—C14D—C13D120.8 (6)
C16B—C17B—H17B119.7C15D—C14D—H14D119.6
O18B—C18B—O19B125.9 (5)C13D—C14D—H14D119.6
O18B—C18B—C10B120.0 (4)C14D—C15D—C16D119.6 (6)
O19B—C18B—C10B114.0 (4)C14D—C15D—H15D120.2
C6C—N1C—C2C121.5 (4)C16D—C15D—H15D120.2
C6C—N1C—C7C120.7 (4)C15D—C16D—C17D119.8 (6)
C2C—N1C—C7C117.7 (4)C15D—C16D—H16D120.1
O2C—C2C—N3C122.1 (4)C17D—C16D—H16D120.1
O2C—C2C—N1C122.6 (4)C12D—C17D—C16D121.5 (6)
N3C—C2C—N1C115.3 (4)C12D—C17D—H17D119.2
C4C—N3C—C2C124.8 (4)C16D—C17D—H17D119.2
C4C—N3C—H3C117.6O19D—C18D—O18D124.8 (5)
C2C—N3C—H3C117.6O19D—C18D—C10D119.4 (4)
N4C—C4C—N3C119.1 (5)O18D—C18D—C10D115.8 (4)
N4C—C4C—C5C123.3 (5)
C6A—N1A—C2A—O2A177.0 (5)C2C—N3C—C4C—N4C177.8 (5)
C7A—N1A—C2A—O2A7.4 (7)C2C—N3C—C4C—C5C3.5 (7)
C6A—N1A—C2A—N3A3.2 (7)N4C—C4C—C5C—C6C178.3 (5)
C7A—N1A—C2A—N3A172.3 (4)N3C—C4C—C5C—C6C0.4 (8)
O2A—C2A—N3A—C4A179.5 (5)C4C—C5C—C6C—N1C1.9 (9)
N1A—C2A—N3A—C4A0.8 (7)C2C—N1C—C6C—C5C0.3 (8)
C2A—N3A—C4A—N4A178.8 (5)C7C—N1C—C6C—C5C177.0 (5)
C2A—N3A—C4A—C5A2.1 (8)C6C—N1C—C7C—C8C98.5 (5)
N4A—C4A—C5A—C6A178.2 (6)C2C—N1C—C7C—C8C78.4 (5)
N3A—C4A—C5A—C6A2.7 (9)N1C—C7C—C8C—C9C61.1 (5)
C4A—C5A—C6A—N1A0.4 (9)C7C—C8C—C9C—O9C53.6 (6)
C2A—N1A—C6A—C5A2.7 (8)C7C—C8C—C9C—N10C124.4 (5)
C7A—N1A—C6A—C5A172.7 (5)O9C—C9C—N10C—C10C2.7 (7)
C6A—N1A—C7A—C8A110.1 (5)C8C—C9C—N10C—C10C179.2 (4)
C2A—N1A—C7A—C8A74.4 (5)C9C—N10C—C10C—C18C71.8 (6)
N1A—C7A—C8A—C9A66.3 (5)C9C—N10C—C10C—C11C164.5 (4)
C7A—C8A—C9A—O9A30.3 (7)N10C—C10C—C11C—C12C71.6 (5)
C7A—C8A—C9A—N10A150.0 (4)C18C—C10C—C11C—C12C165.1 (4)
O9A—C9A—N10A—C10A1.4 (8)N10C—C10C—C11C—C12'C77 (3)
C8A—C9A—N10A—C10A178.8 (4)C18C—C10C—C11C—C12'C160 (3)
C9A—N10A—C10A—C11A135.4 (5)C10C—C11C—C12C—C13C92.9 (4)
C9A—N10A—C10A—C18A100.3 (5)C10C—C11C—C12C—C17C83.9 (5)
N10A—C10A—C11A—C12A53.9 (6)C17C—C12C—C13C—C14C0.0
C18A—C10A—C11A—C12A179.7 (5)C11C—C12C—C13C—C14C176.7 (4)
C10A—C11A—C12A—C13A47.3 (8)C12C—C13C—C14C—C15C0.0
C10A—C11A—C12A—C17A133.7 (6)C13C—C14C—C15C—C16C0.0
C17A—C12A—C13A—C14A0.4 (9)C14C—C15C—C16C—C17C0.0
C11A—C12A—C13A—C14A178.6 (5)C15C—C16C—C17C—C12C0.0
C12A—C13A—C14A—C15A1.1 (9)C13C—C12C—C17C—C16C0.0
C13A—C14A—C15A—C16A0.5 (10)C11C—C12C—C17C—C16C176.8 (4)
C14A—C15A—C16A—C17A0.7 (12)C10C—C11C—C12'C—C13'C93 (5)
C13A—C12A—C17A—C16A0.8 (10)C10C—C11C—C12'C—C17'C89 (5)
C11A—C12A—C17A—C16A179.8 (7)C17'C—C12'C—C13'C—C14'C0
C15A—C16A—C17A—C12A1.4 (13)C11C—C12'C—C13'C—C14'C179
N10A—C10A—C18A—O18A35.2 (7)C12'C—C13'C—C14'C—C15'C2
C11A—C10A—C18A—O18A89.3 (6)C13'C—C14'C—C15'C—C16'C3
N10A—C10A—C18A—O19A146.5 (5)C14'C—C15'C—C16'C—C17'C4
C11A—C10A—C18A—O19A89.0 (6)C15'C—C16'C—C17'C—C12'C3
C6B—N1B—C2B—O2B172.4 (4)C13'C—C12'C—C17'C—C16'C2
C7B—N1B—C2B—O2B3.0 (6)C11C—C12'C—C17'C—C16'C179 (3)
C6B—N1B—C2B—N3B6.6 (6)N10C—C10C—C18C—O19C23.0 (7)
C7B—N1B—C2B—N3B178.0 (4)C11C—C10C—C18C—O19C100.3 (6)
O2B—C2B—N3B—C4B172.5 (5)N10C—C10C—C18C—O18C158.2 (4)
N1B—C2B—N3B—C4B6.5 (7)C11C—C10C—C18C—O18C78.6 (6)
C2B—N3B—C4B—N4B177.5 (5)C6D—N1D—C2D—O2D175.8 (5)
C2B—N3B—C4B—C5B3.3 (8)C7D—N1D—C2D—O2D1.0 (7)
N4B—C4B—C5B—C6B179.1 (5)C6D—N1D—C2D—N3D2.4 (7)
N3B—C4B—C5B—C6B0.1 (8)C7D—N1D—C2D—N3D179.2 (4)
C4B—C5B—C6B—N1B0.1 (8)O2D—C2D—N3D—C4D173.9 (5)
C2B—N1B—C6B—C5B3.6 (7)N1D—C2D—N3D—C4D4.3 (7)
C7B—N1B—C6B—C5B178.8 (5)C2D—N3D—C4D—N4D177.8 (5)
C6B—N1B—C7B—C8B97.0 (5)C2D—N3D—C4D—C5D2.9 (8)
C2B—N1B—C7B—C8B78.4 (5)N4D—C4D—C5D—C6D178.8 (6)
N1B—C7B—C8B—C9B61.7 (5)N3D—C4D—C5D—C6D0.5 (8)
C7B—C8B—C9B—O9B32.8 (6)C4D—C5D—C6D—N1D2.2 (9)
C7B—C8B—C9B—N10B148.0 (4)C2D—N1D—C6D—C5D0.7 (8)
O9B—C9B—N10B—C10B0.7 (7)C7D—N1D—C6D—C5D176.1 (5)
C8B—C9B—N10B—C10B179.9 (4)C6D—N1D—C7D—C8D96.3 (5)
C9B—N10B—C10B—C11B141.4 (5)C2D—N1D—C7D—C8D80.6 (5)
C9B—N10B—C10B—C18B98.0 (5)N1D—C7D—C8D—C9D64.2 (5)
N10B—C10B—C11B—C12B63.7 (6)C7D—C8D—C9D—O9D54.7 (6)
C18B—C10B—C11B—C12B173.1 (4)C7D—C8D—C9D—N10D124.2 (4)
C10B—C11B—C12B—C17B159.4 (5)O9D—C9D—N10D—C10D2.7 (7)
C10B—C11B—C12B—C13B24.7 (7)C8D—C9D—N10D—C10D178.4 (4)
C17B—C12B—C13B—C14B2.1 (8)C9D—N10D—C10D—C11D163.8 (4)
C11B—C12B—C13B—C14B173.8 (5)C9D—N10D—C10D—C18D75.3 (6)
C12B—C13B—C14B—C15B0.9 (9)N10D—C10D—C11D—C12D59.8 (6)
C13B—C14B—C15B—C16B0.3 (9)C18D—C10D—C11D—C12D177.5 (4)
C14B—C15B—C16B—C17B0.1 (10)C10D—C11D—C12D—C17D81.6 (6)
C13B—C12B—C17B—C16B2.3 (9)C10D—C11D—C12D—C13D99.0 (6)
C11B—C12B—C17B—C16B173.8 (5)C17D—C12D—C13D—C14D1.0 (8)
C15B—C16B—C17B—C12B1.2 (10)C11D—C12D—C13D—C14D179.6 (5)
N10B—C10B—C18B—O18B36.9 (6)C12D—C13D—C14D—C15D0.2 (9)
C11B—C10B—C18B—O18B85.0 (5)C13D—C14D—C15D—C16D0.3 (10)
N10B—C10B—C18B—O19B147.0 (4)C14D—C15D—C16D—C17D0.1 (10)
C11B—C10B—C18B—O19B91.0 (5)C13D—C12D—C17D—C16D1.3 (9)
C6C—N1C—C2C—O2C174.9 (5)C11D—C12D—C17D—C16D179.4 (6)
C7C—N1C—C2C—O2C2.0 (7)C15D—C16D—C17D—C12D0.7 (10)
C6C—N1C—C2C—N3C3.8 (7)N10D—C10D—C18D—O19D28.5 (6)
C7C—N1C—C2C—N3C179.4 (4)C11D—C10D—C18D—O19D94.6 (5)
O2C—C2C—N3C—C4C173.2 (5)N10D—C10D—C18D—O18D153.1 (4)
N1C—C2C—N3C—C4C5.5 (7)C11D—C10D—C18D—O18D83.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3A—H3A···O18Di0.881.752.623 (6)171
N4A—H4AA···O19Di0.881.942.811 (7)173
N10A—H10A···O19Cii0.882.193.036 (6)161
N3B—H3B···O18Ciii0.881.732.565 (6)159
N4B—H4AB···O19Ciii0.882.142.965 (7)156
N4B—H4BB···O2Aiv0.882.422.934 (7)118
N10B—H10B···O19Di0.882.052.885 (6)159
N3C—H3C···O19B0.881.742.601 (5)167
N4C—H4AC···O18B0.882.052.903 (6)164
N4C—H4BC···O19Av0.882.283.090 (7)154
N10C—H10C···O18Avi0.882.032.890 (5)167
N3D—H3D···O19Avi0.881.752.615 (5)168
N4D—H4AD···O18Avi0.882.062.920 (6)165
N4D—H4BD···O19B0.882.233.047 (6)155
N10D—H10D···O18Biv0.882.102.945 (5)162
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z1; (iii) x+1, y, z1; (iv) x, y1, z; (v) x1, y, z+1; (vi) x1, y1, z+1.
(II) N-[2-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)propionyl]-L-serine monohydrate top
Crystal data top
C10H14N4O5·H2OZ = 2
Mr = 288.27F(000) = 304
Triclinic, P1Dx = 1.516 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.863 (1) ÅCell parameters from 1717 reflections
b = 10.771 (2) Åθ = 3.4–28.7°
c = 12.228 (2) ŵ = 0.13 mm1
α = 80.45 (3)°T = 100 K
β = 89.23 (3)°Plate, colourless
γ = 88.61 (3)°0.25 × 0.25 × 0.06 mm
V = 631.4 (2) Å3
Data collection top
Bruker SMART APEX
diffractometer
2336 independent reflections
Radiation source: MacScience, M18XCE rotating anode2284 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 8.366 pixels mm-1θmax = 25.7°, θmin = 1.7°
ω scansh = 54
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1013
Tmin = 0.827, Tmax = 0.993l = 1414
3919 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.17 w = 1/[σ2(Fo2) + (0.0615P)2 + 0.1838P]
where P = (Fo2 + 2Fc2)/3
2336 reflections(Δ/σ)max = 0.007
377 parametersΔρmax = 0.32 e Å3
3 restraintsΔρmin = 0.25 e Å3
Crystal data top
C10H14N4O5·H2Oγ = 88.61 (3)°
Mr = 288.27V = 631.4 (2) Å3
Triclinic, P1Z = 2
a = 4.863 (1) ÅMo Kα radiation
b = 10.771 (2) ŵ = 0.13 mm1
c = 12.228 (2) ÅT = 100 K
α = 80.45 (3)°0.25 × 0.25 × 0.06 mm
β = 89.23 (3)°
Data collection top
Bruker SMART APEX
diffractometer
2336 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
2284 reflections with I > 2σ(I)
Tmin = 0.827, Tmax = 0.993Rint = 0.022
3919 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0483 restraints
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.17Δρmax = 0.32 e Å3
2336 reflectionsΔρmin = 0.25 e Å3
377 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. 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
N1A0.9036 (7)0.2485 (3)0.2358 (3)0.0128 (7)
C2A1.1159 (8)0.1800 (4)0.2948 (3)0.0123 (8)
O2A1.1824 (6)0.1964 (3)0.3875 (2)0.0162 (6)
N3A1.2527 (7)0.0930 (3)0.2414 (3)0.0135 (7)
H3A1.39130.05020.27610.016*
C4A1.1896 (8)0.0681 (4)0.1388 (3)0.0118 (8)
N4A1.3306 (7)0.0180 (3)0.0976 (3)0.0150 (8)
H4AA1.46540.05970.13590.018*
H4BA1.29100.03450.03160.018*
C5A0.9696 (9)0.1400 (4)0.0815 (3)0.0152 (9)
H5A0.91830.12690.00970.018*
C6A0.8353 (8)0.2273 (4)0.1315 (3)0.0131 (8)
H6A0.68910.27550.09340.016*
C7A0.7538 (8)0.3456 (4)0.2875 (3)0.0129 (8)
H7AA0.70540.31040.36520.015*
H7BA0.58090.37030.24690.015*
C8A0.9314 (9)0.4620 (4)0.2852 (3)0.0149 (9)
H8AA1.10710.43660.32350.018*
H8BA0.97450.49860.20740.018*
C9A0.7850 (8)0.5600 (4)0.3412 (3)0.0122 (8)
O9A0.5310 (6)0.5628 (3)0.3529 (2)0.0173 (6)
N10A0.9470 (7)0.6443 (3)0.3756 (3)0.0126 (7)
H10A1.12630.63680.36710.015*
C10A0.8356 (8)0.7478 (4)0.4266 (3)0.0132 (8)
H10AA0.68160.71470.47730.016*
C11A1.0556 (9)0.7948 (4)0.4967 (3)0.0162 (9)
H11AA1.21660.82220.44910.019*
H11BA0.98190.86840.52730.019*
O11A1.1408 (7)0.6985 (3)0.5857 (3)0.0263 (8)
H11A1.11450.72400.64640.039*
C12A0.7197 (8)0.8587 (4)0.3416 (3)0.0125 (8)
O12A0.7184 (7)0.8470 (3)0.2413 (2)0.0201 (7)
O13A0.6306 (6)0.9549 (3)0.3792 (2)0.0159 (6)
N1B0.8068 (7)0.2635 (3)0.7485 (3)0.0152 (8)
C2B0.5983 (8)0.1943 (4)0.8047 (3)0.0117 (8)
O2B0.5115 (6)0.2101 (3)0.8950 (2)0.0176 (7)
N3B0.4905 (7)0.1026 (3)0.7497 (3)0.0119 (7)
H3B0.35850.05610.78360.014*
C4B0.5731 (8)0.0793 (4)0.6474 (3)0.0118 (8)
N4B0.4556 (7)0.0093 (3)0.6049 (3)0.0147 (8)
H4AB0.32430.05350.64190.018*
H4BB0.50770.02480.53920.018*
C5B0.7866 (9)0.1556 (4)0.5935 (4)0.0163 (9)
H5B0.85260.14420.52230.020*
C6B0.8926 (9)0.2438 (4)0.6451 (3)0.0167 (9)
H6B1.03340.29510.60850.020*
C7B0.9290 (9)0.3646 (4)0.8000 (4)0.0166 (9)
H7AB1.11470.38280.76800.020*
H7BB0.94910.33520.88060.020*
C8B0.7530 (9)0.4845 (4)0.7813 (4)0.0185 (9)
H8AB0.56740.46630.81340.022*
H8BB0.73270.51390.70070.022*
C9B0.8782 (8)0.5881 (4)0.8339 (3)0.0130 (9)
O9B1.1280 (6)0.5869 (3)0.8556 (2)0.0164 (6)
N10B0.7037 (7)0.6815 (3)0.8520 (3)0.0135 (7)
H10B0.53040.67780.83320.016*
C10B0.7891 (9)0.7895 (4)0.9017 (3)0.0134 (8)
H10AB0.62270.84590.90160.016*
C11B0.8679 (9)0.7501 (4)1.0232 (3)0.0167 (9)
H11AB1.02450.68901.02900.020*
H11BB0.92550.82471.05400.020*
O11B0.6389 (7)0.6945 (3)1.0846 (2)0.0207 (7)
H11B0.63380.71641.14740.031*
C12B1.0092 (8)0.8683 (4)0.8336 (3)0.0131 (8)
O12B1.0536 (7)0.8548 (3)0.7350 (2)0.0214 (7)
O13B1.1254 (6)0.9495 (3)0.8803 (2)0.0165 (6)
O1C0.3425 (7)0.4514 (3)0.5734 (3)0.0235 (7)
H1C0.244 (11)0.527 (5)0.565 (4)0.017 (12)*
H2C0.420 (14)0.465 (6)0.507 (5)0.045 (18)*
O1D0.4008 (8)0.4616 (3)1.0599 (3)0.0265 (8)
H1D0.523 (17)0.525 (7)1.047 (6)0.07 (2)*
H2D0.306 (15)0.484 (6)1.007 (6)0.05 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0167 (19)0.0098 (17)0.0124 (17)0.0012 (14)0.0002 (14)0.0033 (13)
C2A0.013 (2)0.011 (2)0.013 (2)0.0029 (16)0.0027 (16)0.0031 (16)
O2A0.0217 (16)0.0171 (15)0.0103 (14)0.0024 (12)0.0024 (12)0.0041 (11)
N3A0.0136 (17)0.0144 (17)0.0124 (17)0.0030 (14)0.0049 (14)0.0019 (13)
C4A0.015 (2)0.0092 (19)0.0121 (19)0.0073 (16)0.0009 (16)0.0023 (15)
N4A0.0193 (19)0.0179 (19)0.0095 (16)0.0012 (15)0.0030 (14)0.0070 (13)
C5A0.018 (2)0.019 (2)0.0096 (19)0.0057 (17)0.0025 (16)0.0015 (16)
C6A0.013 (2)0.012 (2)0.015 (2)0.0047 (16)0.0022 (16)0.0032 (15)
C7A0.011 (2)0.012 (2)0.016 (2)0.0016 (16)0.0042 (16)0.0051 (16)
C8A0.014 (2)0.015 (2)0.016 (2)0.0026 (16)0.0020 (16)0.0030 (16)
C9A0.016 (2)0.010 (2)0.0108 (19)0.0009 (16)0.0003 (16)0.0026 (15)
O9A0.0106 (15)0.0223 (16)0.0212 (15)0.0035 (12)0.0017 (11)0.0095 (12)
N10A0.0081 (17)0.0173 (18)0.0126 (17)0.0056 (14)0.0002 (13)0.0037 (13)
C10A0.015 (2)0.012 (2)0.0127 (19)0.0003 (16)0.0013 (16)0.0043 (15)
C11A0.020 (2)0.017 (2)0.014 (2)0.0020 (17)0.0053 (17)0.0072 (16)
O11A0.042 (2)0.0209 (17)0.0174 (16)0.0131 (15)0.0146 (15)0.0082 (13)
C12A0.0098 (19)0.014 (2)0.015 (2)0.0017 (16)0.0007 (15)0.0071 (16)
O12A0.0317 (19)0.0192 (16)0.0108 (14)0.0070 (13)0.0036 (13)0.0077 (12)
O13A0.0204 (16)0.0145 (15)0.0135 (14)0.0035 (12)0.0039 (12)0.0050 (11)
N1B0.0156 (19)0.0151 (18)0.0143 (18)0.0030 (14)0.0045 (15)0.0001 (14)
C2B0.011 (2)0.009 (2)0.014 (2)0.0052 (16)0.0067 (16)0.0010 (15)
O2B0.0207 (17)0.0223 (17)0.0103 (15)0.0014 (13)0.0001 (12)0.0045 (12)
N3B0.0099 (17)0.0110 (17)0.0148 (16)0.0023 (13)0.0013 (13)0.0014 (13)
C4B0.0111 (19)0.013 (2)0.0098 (19)0.0050 (16)0.0013 (15)0.0020 (15)
N4B0.0196 (19)0.0137 (18)0.0112 (17)0.0008 (15)0.0015 (14)0.0033 (14)
C5B0.017 (2)0.015 (2)0.017 (2)0.0024 (17)0.0002 (17)0.0014 (17)
C6B0.016 (2)0.017 (2)0.016 (2)0.0003 (17)0.0039 (17)0.0024 (17)
C7B0.020 (2)0.011 (2)0.018 (2)0.0033 (17)0.0057 (17)0.0022 (17)
C8B0.022 (2)0.014 (2)0.019 (2)0.0011 (18)0.0034 (19)0.0036 (17)
C9B0.013 (2)0.017 (2)0.0082 (18)0.0010 (16)0.0013 (16)0.0019 (16)
O9B0.0126 (15)0.0172 (16)0.0213 (16)0.0014 (12)0.0031 (12)0.0082 (12)
N10B0.0100 (17)0.0175 (18)0.0147 (17)0.0040 (14)0.0024 (14)0.0068 (14)
C10B0.016 (2)0.015 (2)0.0102 (19)0.0017 (16)0.0007 (15)0.0033 (15)
C11B0.023 (2)0.017 (2)0.011 (2)0.0040 (18)0.0017 (17)0.0039 (16)
O11B0.0301 (18)0.0226 (16)0.0108 (14)0.0114 (14)0.0086 (13)0.0056 (12)
C12B0.012 (2)0.013 (2)0.015 (2)0.0003 (16)0.0029 (16)0.0049 (16)
O12B0.0333 (19)0.0214 (17)0.0115 (15)0.0102 (14)0.0072 (13)0.0074 (12)
O13B0.0204 (16)0.0180 (15)0.0118 (14)0.0085 (12)0.0029 (11)0.0040 (11)
O1C0.0296 (19)0.0199 (18)0.0197 (17)0.0019 (15)0.0018 (14)0.0001 (13)
O1D0.032 (2)0.0205 (18)0.0253 (18)0.0024 (15)0.0107 (16)0.0006 (14)
Geometric parameters (Å, º) top
N1A—C6A1.378 (5)N1B—C7B1.485 (5)
N1A—C2A1.392 (5)C2B—O2B1.214 (5)
N1A—C7A1.482 (5)C2B—N3B1.398 (5)
C2A—O2A1.224 (5)N3B—C4B1.369 (5)
C2A—N3A1.382 (5)N3B—H3B0.8800
N3A—C4A1.366 (5)C4B—N4B1.307 (5)
N3A—H3A0.8800C4B—C5B1.425 (6)
C4A—N4A1.304 (6)N4B—H4AB0.8800
C4A—C5A1.426 (6)N4B—H4BB0.8800
N4A—H4AA0.8800C5B—C6B1.341 (6)
N4A—H4BA0.8800C5B—H5B0.9500
C5A—C6A1.354 (6)C6B—H6B0.9500
C5A—H5A0.9500C7B—C8B1.519 (6)
C6A—H6A0.9500C7B—H7AB0.9900
C7A—C8A1.536 (6)C7B—H7BB0.9900
C7A—H7AA0.9900C8B—C9B1.520 (6)
C7A—H7BA0.9900C8B—H8AB0.9900
C8A—C9A1.510 (6)C8B—H8BB0.9900
C8A—H8AA0.9900C9B—O9B1.246 (5)
C8A—H8BA0.9900C9B—N10B1.345 (5)
C9A—O9A1.242 (5)N10B—C10B1.470 (5)
C9A—N10A1.339 (5)N10B—H10B0.8800
N10A—C10A1.456 (5)C10B—C11B1.527 (5)
N10A—H10A0.8800C10B—C12B1.532 (6)
C10A—C11A1.526 (6)C10B—H10AB1.0000
C10A—C12A1.548 (6)C11B—O11B1.422 (5)
C10A—H10AA1.0000C11B—H11AB0.9900
C11A—O11A1.431 (5)C11B—H11BB0.9900
C11A—H11AA0.9900O11B—H11B0.8400
C11A—H11BA0.9900C12B—O12B1.253 (5)
O11A—H11A0.8400C12B—O13B1.269 (5)
C12A—O12A1.253 (5)O1C—H1C0.93 (6)
C12A—O13A1.266 (5)O1C—H2C0.88 (7)
N1B—C2B1.380 (5)O1D—H1D0.91 (8)
N1B—C6B1.374 (6)O1D—H2D0.80 (7)
C6A—N1A—C2A121.0 (4)C2B—N1B—C7B118.5 (3)
C6A—N1A—C7A120.7 (3)C6B—N1B—C7B120.2 (4)
C2A—N1A—C7A118.3 (3)O2B—C2B—N1B123.6 (4)
O2A—C2A—N3A121.5 (4)O2B—C2B—N3B121.4 (4)
O2A—C2A—N1A122.8 (4)N1B—C2B—N3B115.0 (4)
N3A—C2A—N1A115.8 (3)C4B—N3B—C2B125.4 (4)
C4A—N3A—C2A125.1 (4)C4B—N3B—H3B117.3
C4A—N3A—H3A117.5C2B—N3B—H3B117.3
C2A—N3A—H3A117.5N4B—C4B—N3B119.5 (4)
N4A—C4A—N3A119.5 (4)N4B—C4B—C5B123.9 (4)
N4A—C4A—C5A123.2 (4)N3B—C4B—C5B116.6 (4)
N3A—C4A—C5A117.2 (4)C4B—N4B—H4AB120.0
C4A—N4A—H4AA120.0C4B—N4B—H4BB120.0
C4A—N4A—H4BA120.0H4AB—N4B—H4BB120.0
H4AA—N4A—H4BA120.0C6B—C5B—C4B118.8 (4)
C6A—C5A—C4A118.7 (4)C6B—C5B—H5B120.6
C6A—C5A—H5A120.6C4B—C5B—H5B120.6
C4A—C5A—H5A120.6C5B—C6B—N1B123.0 (4)
C5A—C6A—N1A122.2 (4)C5B—C6B—H6B118.5
C5A—C6A—H6A118.9N1B—C6B—H6B118.5
N1A—C6A—H6A118.9N1B—C7B—C8B111.7 (3)
N1A—C7A—C8A110.5 (3)N1B—C7B—H7AB109.3
N1A—C7A—H7AA109.5C8B—C7B—H7AB109.3
C8A—C7A—H7AA109.5N1B—C7B—H7BB109.3
N1A—C7A—H7BA109.5C8B—C7B—H7BB109.3
C8A—C7A—H7BA109.5H7AB—C7B—H7BB107.9
H7AA—C7A—H7BA108.1C7B—C8B—C9B111.7 (4)
C9A—C8A—C7A111.1 (3)C7B—C8B—H8AB109.3
C9A—C8A—H8AA109.4C9B—C8B—H8AB109.3
C7A—C8A—H8AA109.4C7B—C8B—H8BB109.3
C9A—C8A—H8BA109.4C9B—C8B—H8BB109.3
C7A—C8A—H8BA109.4H8AB—C8B—H8BB107.9
H8AA—C8A—H8BA108.0O9B—C9B—N10B122.9 (4)
O9A—C9A—N10A122.5 (4)O9B—C9B—C8B121.5 (4)
O9A—C9A—C8A122.0 (4)N10B—C9B—C8B115.6 (3)
N10A—C9A—C8A115.5 (4)C9B—N10B—C10B123.0 (3)
C9A—N10A—C10A122.0 (3)C9B—N10B—H10B118.5
C9A—N10A—H10A119.0C10B—N10B—H10B118.5
C10A—N10A—H10A119.0N10B—C10B—C11B111.7 (3)
N10A—C10A—C11A109.9 (3)N10B—C10B—C12B113.4 (3)
N10A—C10A—C12A113.3 (3)C11B—C10B—C12B112.8 (3)
C11A—C10A—C12A109.9 (3)N10B—C10B—H10AB106.1
N10A—C10A—H10AA107.9C11B—C10B—H10AB106.1
C11A—C10A—H10AA107.9C12B—C10B—H10AB106.1
C12A—C10A—H10AA107.9O11B—C11B—C10B109.6 (3)
O11A—C11A—C10A111.3 (4)O11B—C11B—H11AB109.7
O11A—C11A—H11AA109.4C10B—C11B—H11AB109.7
C10A—C11A—H11AA109.4O11B—C11B—H11BB109.7
O11A—C11A—H11BA109.4C10B—C11B—H11BB109.7
C10A—C11A—H11BA109.4H11AB—C11B—H11BB108.2
H11AA—C11A—H11BA108.0C11B—O11B—H11B109.5
C11A—O11A—H11A109.5O12B—C12B—O13B124.0 (4)
O12A—C12A—O13A124.7 (4)O12B—C12B—C10B119.4 (3)
O12A—C12A—C10A118.3 (4)O13B—C12B—C10B116.5 (4)
O13A—C12A—C10A117.0 (3)H1C—O1C—H2C95 (5)
C2B—N1B—C6B121.2 (4)H1D—O1D—H2D97 (6)
C6A—N1A—C2A—O2A180.0 (4)C6B—N1B—C2B—O2B178.3 (4)
C7A—N1A—C2A—O2A0.4 (5)C7B—N1B—C2B—O2B1.2 (6)
C6A—N1A—C2A—N3A1.1 (5)C6B—N1B—C2B—N3B1.6 (5)
C7A—N1A—C2A—N3A178.5 (3)C7B—N1B—C2B—N3B178.7 (3)
O2A—C2A—N3A—C4A179.2 (4)O2B—C2B—N3B—C4B179.2 (4)
N1A—C2A—N3A—C4A1.9 (6)N1B—C2B—N3B—C4B0.8 (5)
C2A—N3A—C4A—N4A178.7 (4)C2B—N3B—C4B—N4B180.0 (3)
C2A—N3A—C4A—C5A1.6 (6)C2B—N3B—C4B—C5B0.1 (6)
N4A—C4A—C5A—C6A179.9 (4)N4B—C4B—C5B—C6B179.9 (4)
N3A—C4A—C5A—C6A0.5 (6)N3B—C4B—C5B—C6B0.2 (6)
C4A—C5A—C6A—N1A0.2 (6)C4B—C5B—C6B—N1B0.7 (6)
C2A—N1A—C6A—C5A0.1 (6)C2B—N1B—C6B—C5B1.7 (6)
C7A—N1A—C6A—C5A179.4 (4)C7B—N1B—C6B—C5B178.8 (4)
C6A—N1A—C7A—C8A105.4 (4)C2B—N1B—C7B—C8B80.8 (4)
C2A—N1A—C7A—C8A74.2 (4)C6B—N1B—C7B—C8B96.4 (5)
N1A—C7A—C8A—C9A178.1 (3)N1B—C7B—C8B—C9B179.9 (3)
C7A—C8A—C9A—O9A21.7 (5)C7B—C8B—C9B—O9B21.5 (6)
C7A—C8A—C9A—N10A159.2 (3)C7B—C8B—C9B—N10B160.2 (4)
O9A—C9A—N10A—C10A1.8 (6)O9B—C9B—N10B—C10B1.6 (6)
C8A—C9A—N10A—C10A177.3 (3)C8B—C9B—N10B—C10B179.8 (3)
C9A—N10A—C10A—C11A157.7 (4)C9B—N10B—C10B—C11B67.9 (5)
C9A—N10A—C10A—C12A79.0 (4)C9B—N10B—C10B—C12B60.9 (5)
N10A—C10A—C11A—O11A62.5 (5)N10B—C10B—C11B—O11B59.8 (5)
C12A—C10A—C11A—O11A172.2 (3)C12B—C10B—C11B—O11B171.1 (3)
N10A—C10A—C12A—O12A3.7 (5)N10B—C10B—C12B—O12B15.5 (5)
C11A—C10A—C12A—O12A127.0 (4)C11B—C10B—C12B—O12B143.7 (4)
N10A—C10A—C12A—O13A176.8 (3)N10B—C10B—C12B—O13B168.4 (4)
C11A—C10A—C12A—O13A53.5 (5)C11B—C10B—C12B—O13B40.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3A—H3A···O13Ai0.881.882.747 (4)167
N4A—H4AA···O12Ai0.881.932.805 (5)170
N4A—H4BA···O13Bii0.882.062.928 (5)168
N10A—H10A···O9Aiii0.882.122.975 (5)163
O11A—H11A···O12B0.841.932.704 (5)153
N3B—H3B···O13Biv0.881.892.759 (4)168
N4B—H4AB···O12Biv0.881.912.789 (5)174
N4B—H4BB···O13Av0.882.082.960 (5)175
N10B—H10B···O9Bvi0.882.203.000 (5)150
O11B—H11B···O12Avii0.842.012.759 (4)148
O1C—H1C···O11Avi0.93 (5)1.96 (6)2.841 (5)159 (5)
O1C—H2C···O9A0.88 (6)2.07 (6)2.909 (4)158 (6)
O1D—H1D···O11B0.91 (8)2.05 (8)2.851 (5)146 (7)
O1D—H2D···O9Bvi0.80 (7)2.17 (7)2.951 (4)164 (7)
Symmetry codes: (i) x+1, y1, z; (ii) x, y1, z1; (iii) x+1, y, z; (iv) x1, y1, z; (v) x, y1, z; (vi) x1, y, z; (vii) x, y, z+1.
(III) N-[2-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)propionyl]-L-lysine top
Crystal data top
C13H21N5O4Z = 2
Mr = 311.35F(000) = 332
Triclinic, P1Dx = 1.424 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.9334 (9) ÅCell parameters from 2571 reflections
b = 8.2977 (10) Åθ = 2.5–26.8°
c = 13.2491 (16) ŵ = 0.11 mm1
α = 90.780 (2)°T = 100 K
β = 93.498 (2)°Plate, colourless
γ = 107.293 (2)°0.40 × 0.18 × 0.04 mm
V = 726.02 (16) Å3
Data collection top
Bruker SMART APEX
diffractometer
2970 independent reflections
Radiation source: MacScience, M18XCE rotating anode2714 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 8.366 pixels mm-1θmax = 26.4°, θmin = 1.5°
ω scansh = 88
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1010
Tmin = 0.878, Tmax = 0.996l = 1616
7954 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0707P)2 + 0.0541P]
where P = (Fo2 + 2Fc2)/3
2970 reflections(Δ/σ)max < 0.001
399 parametersΔρmax = 0.34 e Å3
3 restraintsΔρmin = 0.19 e Å3
Crystal data top
C13H21N5O4γ = 107.293 (2)°
Mr = 311.35V = 726.02 (16) Å3
Triclinic, P1Z = 2
a = 6.9334 (9) ÅMo Kα radiation
b = 8.2977 (10) ŵ = 0.11 mm1
c = 13.2491 (16) ÅT = 100 K
α = 90.780 (2)°0.40 × 0.18 × 0.04 mm
β = 93.498 (2)°
Data collection top
Bruker SMART APEX
diffractometer
2970 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
2714 reflections with I > 2σ(I)
Tmin = 0.878, Tmax = 0.996Rint = 0.025
7954 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0383 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 1.00Δρmax = 0.34 e Å3
2970 reflectionsΔρmin = 0.19 e Å3
399 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. 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
N1A0.2314 (3)0.4276 (3)0.11002 (19)0.0163 (5)
C2A0.1058 (4)0.4228 (3)0.1884 (2)0.0153 (6)
O2A0.1817 (3)0.3322 (3)0.26411 (16)0.0216 (5)
N3A0.0903 (4)0.5144 (3)0.17714 (19)0.0177 (5)
C4A0.1667 (4)0.6059 (3)0.0913 (2)0.0165 (6)
N4A0.3620 (4)0.6916 (3)0.08249 (19)0.0203 (5)
H4A10.43930.68820.13230.024*
H4A20.41440.75200.02690.024*
C5A0.0404 (5)0.6137 (3)0.0114 (2)0.0186 (6)
H5A0.09340.67930.04890.022*
C6A0.1563 (5)0.5248 (3)0.0245 (2)0.0182 (6)
H6A0.24460.52970.02680.022*
C7A0.4452 (4)0.3250 (4)0.1216 (2)0.0192 (6)
H7A10.52300.36800.07320.023*
H7A20.50080.33640.19080.023*
C8A0.4715 (4)0.1383 (4)0.1030 (2)0.0176 (6)
H8A10.40280.09260.15470.021*
H8A20.61740.07450.10990.021*
C9A0.3840 (4)0.1139 (3)0.0019 (2)0.0159 (6)
O9A0.4195 (3)0.1864 (3)0.07727 (17)0.0230 (5)
N10A0.2662 (3)0.0123 (3)0.00709 (18)0.0145 (5)
H10A0.24960.04040.04830.017*
C10A0.1646 (4)0.0133 (3)0.1023 (2)0.0157 (6)
H10B0.19870.06000.15460.019*
C11A0.0647 (4)0.0518 (3)0.0949 (2)0.0185 (6)
H11A0.13290.01950.15570.022*
H11B0.10160.00240.03510.022*
C12A0.1396 (4)0.2435 (3)0.0860 (2)0.0191 (6)
H12A0.04710.27760.03670.023*
H12B0.27510.27460.05870.023*
C13A0.1540 (4)0.3436 (4)0.1856 (2)0.0244 (7)
H13A0.02520.29860.21850.029*
H13B0.16800.46260.16990.029*
C14A0.3269 (4)0.3401 (4)0.2607 (2)0.0217 (6)
H14A0.31370.22170.27760.026*
H14B0.31810.40220.32370.026*
N14A0.5282 (4)0.4174 (3)0.2198 (2)0.0192 (5)
H14C0.53080.51750.19180.029*
H14D0.62680.43550.27100.029*
H14E0.55000.34640.17190.029*
C15A0.2445 (4)0.1965 (3)0.1369 (2)0.0147 (6)
O15A0.1286 (3)0.2523 (3)0.19137 (16)0.0221 (5)
O16A0.4266 (3)0.2772 (3)0.11217 (16)0.0191 (5)
N1B0.0615 (3)0.2061 (3)0.32343 (18)0.0159 (5)
C2B0.1870 (5)0.1993 (4)0.2452 (2)0.0180 (6)
O2B0.1130 (3)0.1086 (3)0.16897 (16)0.0213 (5)
N3B0.3857 (4)0.2934 (3)0.25610 (19)0.0177 (5)
C4B0.4595 (4)0.3876 (3)0.3405 (2)0.0170 (6)
N4B0.6565 (4)0.4730 (3)0.3486 (2)0.0217 (6)
H4B10.73360.46630.29930.026*
H4B20.70920.53600.40320.026*
C5B0.3341 (4)0.3999 (3)0.4196 (2)0.0165 (6)
H5B0.38650.46940.47850.020*
C6B0.1384 (5)0.3083 (4)0.4070 (2)0.0180 (6)
H6B0.05030.31490.45800.022*
C7B0.1512 (4)0.1027 (4)0.3154 (2)0.0189 (6)
H7B10.21150.11330.24710.023*
H7B20.22580.14600.36530.023*
C8B0.1764 (4)0.0837 (4)0.3339 (2)0.0198 (6)
H8B10.32250.14670.33040.024*
H8B20.11400.13020.27980.024*
C9B0.0800 (4)0.1095 (3)0.4358 (2)0.0157 (6)
O9B0.1265 (3)0.0526 (3)0.51510 (17)0.0234 (5)
N10B0.0548 (3)0.1943 (3)0.43226 (18)0.0157 (5)
H10C0.07580.22700.37150.019*
C10B0.1732 (4)0.2406 (3)0.5166 (2)0.0155 (6)
H10D0.29000.26490.48560.019*
C11B0.2672 (4)0.0993 (3)0.5952 (2)0.0183 (6)
H11C0.15800.06760.62740.022*
H11D0.34530.14070.64840.022*
C12B0.4060 (4)0.0557 (4)0.5494 (2)0.0202 (6)
H12C0.33020.09210.49290.024*
H12D0.52040.02570.52140.024*
C13B0.4895 (4)0.2027 (4)0.6267 (2)0.0233 (6)
H13C0.54360.30790.58990.028*
H13D0.37680.21570.66520.028*
C14B0.6553 (4)0.1815 (4)0.7010 (2)0.0192 (6)
H14F0.67630.26420.75830.023*
H14G0.61240.06680.72840.023*
N14B0.8501 (4)0.2071 (3)0.6516 (2)0.0205 (5)
H14H0.83600.12200.60510.031*
H14I0.95020.20710.69940.031*
H14J0.88250.30770.62040.031*
C15B0.0597 (5)0.4054 (4)0.5669 (2)0.0208 (7)
O15B0.1675 (4)0.4642 (3)0.62742 (17)0.0282 (5)
O16B0.1228 (3)0.4744 (3)0.54323 (17)0.0242 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0149 (13)0.0147 (12)0.0183 (13)0.0031 (9)0.0004 (10)0.0017 (10)
C2A0.0187 (15)0.0156 (14)0.0132 (14)0.0074 (12)0.0014 (12)0.0016 (11)
O2A0.0207 (11)0.0250 (11)0.0178 (11)0.0053 (9)0.0009 (9)0.0037 (9)
N3A0.0183 (12)0.0165 (12)0.0169 (12)0.0031 (10)0.0018 (10)0.0003 (9)
C4A0.0204 (15)0.0149 (14)0.0151 (15)0.0070 (11)0.0002 (12)0.0042 (11)
N4A0.0201 (13)0.0237 (13)0.0145 (13)0.0027 (10)0.0004 (10)0.0012 (10)
C5A0.0257 (16)0.0143 (14)0.0152 (15)0.0053 (12)0.0006 (12)0.0005 (11)
C6A0.0273 (16)0.0131 (13)0.0161 (15)0.0082 (12)0.0058 (12)0.0005 (11)
C7A0.0154 (15)0.0200 (15)0.0225 (16)0.0056 (12)0.0025 (12)0.0022 (12)
C8A0.0167 (14)0.0208 (14)0.0143 (14)0.0045 (11)0.0013 (11)0.0014 (11)
C9A0.0129 (14)0.0131 (13)0.0197 (15)0.0004 (11)0.0028 (12)0.0003 (11)
O9A0.0264 (12)0.0267 (11)0.0211 (11)0.0158 (9)0.0017 (9)0.0027 (9)
N10A0.0167 (12)0.0132 (11)0.0129 (12)0.0042 (9)0.0014 (9)0.0022 (9)
C10A0.0150 (13)0.0154 (13)0.0169 (14)0.0045 (11)0.0020 (11)0.0009 (10)
C11A0.0141 (13)0.0178 (13)0.0234 (14)0.0051 (10)0.0016 (10)0.0023 (11)
C12A0.0121 (13)0.0202 (14)0.0235 (15)0.0027 (11)0.0010 (11)0.0011 (11)
C13A0.0178 (14)0.0183 (14)0.0364 (17)0.0046 (11)0.0013 (12)0.0044 (13)
C14A0.0204 (14)0.0168 (14)0.0243 (15)0.0001 (11)0.0041 (12)0.0030 (12)
N14A0.0206 (13)0.0188 (13)0.0181 (13)0.0061 (10)0.0001 (10)0.0003 (10)
C15A0.0174 (14)0.0164 (13)0.0095 (13)0.0037 (11)0.0011 (11)0.0033 (11)
O15A0.0205 (11)0.0222 (11)0.0225 (12)0.0056 (9)0.0038 (9)0.0047 (9)
O16A0.0156 (10)0.0198 (10)0.0198 (11)0.0018 (8)0.0007 (8)0.0028 (8)
N1B0.0157 (12)0.0171 (12)0.0154 (13)0.0053 (10)0.0021 (10)0.0007 (10)
C2B0.0226 (15)0.0177 (14)0.0163 (15)0.0099 (12)0.0008 (12)0.0034 (12)
O2B0.0204 (11)0.0253 (11)0.0167 (11)0.0054 (9)0.0013 (9)0.0053 (9)
N3B0.0157 (12)0.0201 (13)0.0167 (13)0.0044 (10)0.0016 (10)0.0021 (10)
C4B0.0177 (14)0.0145 (14)0.0195 (15)0.0063 (11)0.0004 (12)0.0022 (11)
N4B0.0177 (13)0.0242 (13)0.0195 (14)0.0007 (10)0.0029 (11)0.0042 (11)
C5B0.0217 (15)0.0133 (14)0.0142 (14)0.0052 (12)0.0008 (12)0.0007 (11)
C6B0.0212 (15)0.0169 (14)0.0182 (16)0.0089 (11)0.0028 (12)0.0024 (11)
C7B0.0160 (15)0.0221 (15)0.0189 (16)0.0065 (12)0.0001 (12)0.0028 (12)
C8B0.0153 (14)0.0196 (15)0.0219 (16)0.0022 (12)0.0030 (12)0.0012 (12)
C9B0.0151 (14)0.0117 (13)0.0176 (15)0.0000 (11)0.0001 (12)0.0003 (11)
O9B0.0257 (12)0.0265 (11)0.0207 (11)0.0118 (9)0.0026 (9)0.0023 (9)
N10B0.0181 (13)0.0158 (12)0.0126 (12)0.0038 (9)0.0019 (10)0.0009 (9)
C10B0.0140 (13)0.0169 (13)0.0155 (14)0.0045 (11)0.0001 (11)0.0001 (11)
C11B0.0197 (13)0.0152 (13)0.0172 (13)0.0018 (11)0.0032 (10)0.0001 (10)
C12B0.0181 (14)0.0193 (14)0.0216 (15)0.0034 (11)0.0001 (11)0.0038 (12)
C13B0.0234 (15)0.0188 (14)0.0258 (15)0.0043 (12)0.0023 (12)0.0023 (12)
C14B0.0172 (14)0.0183 (14)0.0194 (14)0.0010 (11)0.0012 (11)0.0007 (11)
N14B0.0205 (13)0.0181 (12)0.0211 (13)0.0025 (10)0.0025 (10)0.0002 (10)
C15B0.0274 (17)0.0167 (14)0.0171 (15)0.0046 (13)0.0031 (13)0.0031 (12)
O15B0.0371 (14)0.0206 (11)0.0233 (13)0.0046 (10)0.0075 (11)0.0042 (9)
O16B0.0221 (12)0.0228 (11)0.0228 (12)0.0010 (9)0.0028 (9)0.0004 (9)
Geometric parameters (Å, º) top
N1A—C6A1.364 (4)N1B—C6B1.365 (4)
N1A—C2A1.402 (4)N1B—C2B1.403 (4)
N1A—C7A1.471 (4)N1B—C7B1.466 (4)
C2A—O2A1.236 (4)C2B—O2B1.240 (4)
C2A—N3A1.344 (4)C2B—N3B1.364 (4)
N3A—C4A1.347 (4)N3B—C4B1.338 (4)
C4A—N4A1.326 (4)C4B—N4B1.336 (4)
C4A—C5A1.427 (4)C4B—C5B1.424 (4)
N4A—H4A10.8800N4B—H4B10.8800
N4A—H4A20.8800N4B—H4B20.8800
C5A—C6A1.343 (4)C5B—C6B1.343 (4)
C5A—H5A0.9500C5B—H5B0.9500
C6A—H6A0.9500C6B—H6B0.9500
C7A—C8A1.530 (4)C7B—C8B1.529 (4)
C7A—H7A10.9900C7B—H7B10.9900
C7A—H7A20.9900C7B—H7B20.9900
C8A—C9A1.522 (4)C8B—C9B1.515 (4)
C8A—H8A10.9900C8B—H8B10.9900
C8A—H8A20.9900C8B—H8B20.9900
C9A—O9A1.234 (4)C9B—O9B1.245 (3)
C9A—N10A1.336 (4)C9B—N10B1.329 (4)
N10A—C10A1.456 (4)N10B—C10B1.468 (4)
N10A—H10A0.8800N10B—H10C0.8800
C10A—C11A1.529 (4)C10B—C11B1.521 (4)
C10A—C15A1.542 (4)C10B—C15B1.544 (4)
C10A—H10B1.0000C10B—H10D1.0000
C11A—C12A1.529 (4)C11B—C12B1.518 (4)
C11A—H11A0.9900C11B—H11C0.9900
C11A—H11B0.9900C11B—H11D0.9900
C12A—C13A1.531 (4)C12B—C13B1.531 (4)
C12A—H12A0.9900C12B—H12C0.9900
C12A—H12B0.9900C12B—H12D0.9900
C13A—C14A1.517 (4)C13B—C14B1.519 (4)
C13A—H13A0.9900C13B—H13C0.9900
C13A—H13B0.9900C13B—H13D0.9900
C14A—N14A1.490 (4)C14B—N14B1.496 (4)
C14A—H14A0.9900C14B—H14F0.9900
C14A—H14B0.9900C14B—H14G0.9900
N14A—H14C0.9100N14B—H14H0.9100
N14A—H14D0.9100N14B—H14I0.9100
N14A—H14E0.9100N14B—H14J0.9100
C15A—O15A1.241 (4)C15B—O16B1.242 (4)
C15A—O16A1.261 (3)C15B—O15B1.262 (4)
C6A—N1A—C2A120.6 (2)C6B—N1B—C2B119.9 (2)
C6A—N1A—C7A120.7 (2)C6B—N1B—C7B120.2 (2)
C2A—N1A—C7A118.8 (2)C2B—N1B—C7B119.9 (2)
O2A—C2A—N3A123.3 (3)O2B—C2B—N3B122.5 (3)
O2A—C2A—N1A117.9 (2)O2B—C2B—N1B118.8 (3)
N3A—C2A—N1A118.8 (2)N3B—C2B—N1B118.6 (3)
C4A—N3A—C2A120.8 (2)C4B—N3B—C2B120.4 (2)
N4A—C4A—N3A118.8 (3)N4B—C4B—N3B118.0 (3)
N4A—C4A—C5A120.1 (3)N4B—C4B—C5B120.1 (3)
N3A—C4A—C5A121.0 (3)N3B—C4B—C5B121.9 (3)
C4A—N4A—H4A1120.0C4B—N4B—H4B1120.0
C4A—N4A—H4A2120.0C4B—N4B—H4B2120.0
H4A1—N4A—H4A2120.0H4B1—N4B—H4B2120.0
C6A—C5A—C4A117.6 (3)C6B—C5B—C4B116.8 (3)
C6A—C5A—H5A121.2C6B—C5B—H5B121.6
C4A—C5A—H5A121.2C4B—C5B—H5B121.6
C5A—C6A—N1A121.2 (3)C5B—C6B—N1B122.3 (3)
C5A—C6A—H6A119.4C5B—C6B—H6B118.9
N1A—C6A—H6A119.4N1B—C6B—H6B118.9
N1A—C7A—C8A112.0 (2)N1B—C7B—C8B112.5 (2)
N1A—C7A—H7A1109.2N1B—C7B—H7B1109.1
C8A—C7A—H7A1109.2C8B—C7B—H7B1109.1
N1A—C7A—H7A2109.2N1B—C7B—H7B2109.1
C8A—C7A—H7A2109.2C8B—C7B—H7B2109.1
H7A1—C7A—H7A2107.9H7B1—C7B—H7B2107.8
C9A—C8A—C7A111.4 (2)C9B—C8B—C7B112.2 (2)
C9A—C8A—H8A1109.3C9B—C8B—H8B1109.2
C7A—C8A—H8A1109.3C7B—C8B—H8B1109.2
C9A—C8A—H8A2109.3C9B—C8B—H8B2109.2
C7A—C8A—H8A2109.3C7B—C8B—H8B2109.2
H8A1—C8A—H8A2108.0H8B1—C8B—H8B2107.9
O9A—C9A—N10A122.4 (3)O9B—C9B—N10B124.2 (3)
O9A—C9A—C8A121.0 (3)O9B—C9B—C8B120.8 (3)
N10A—C9A—C8A116.5 (2)N10B—C9B—C8B115.0 (3)
C9A—N10A—C10A121.5 (2)C9B—N10B—C10B128.4 (2)
C9A—N10A—H10A119.2C9B—N10B—H10C115.8
C10A—N10A—H10A119.2C10B—N10B—H10C115.8
N10A—C10A—C11A109.4 (2)N10B—C10B—C11B114.5 (2)
N10A—C10A—C15A112.1 (2)N10B—C10B—C15B113.7 (2)
C11A—C10A—C15A114.9 (2)C11B—C10B—C15B111.2 (2)
N10A—C10A—H10B106.6N10B—C10B—H10D105.5
C11A—C10A—H10B106.6C11B—C10B—H10D105.5
C15A—C10A—H10B106.6C15B—C10B—H10D105.5
C10A—C11A—C12A112.1 (2)C12B—C11B—C10B112.2 (2)
C10A—C11A—H11A109.2C12B—C11B—H11C109.2
C12A—C11A—H11A109.2C10B—C11B—H11C109.2
C10A—C11A—H11B109.2C12B—C11B—H11D109.2
C12A—C11A—H11B109.2C10B—C11B—H11D109.2
H11A—C11A—H11B107.9H11C—C11B—H11D107.9
C13A—C12A—C11A114.6 (2)C11B—C12B—C13B112.5 (2)
C13A—C12A—H12A108.6C11B—C12B—H12C109.1
C11A—C12A—H12A108.6C13B—C12B—H12C109.1
C13A—C12A—H12B108.6C11B—C12B—H12D109.1
C11A—C12A—H12B108.6C13B—C12B—H12D109.1
H12A—C12A—H12B107.6H12C—C12B—H12D107.8
C14A—C13A—C12A115.5 (2)C14B—C13B—C12B114.2 (2)
C14A—C13A—H13A108.4C14B—C13B—H13C108.7
C12A—C13A—H13A108.4C12B—C13B—H13C108.7
C14A—C13A—H13B108.4C14B—C13B—H13D108.7
C12A—C13A—H13B108.4C12B—C13B—H13D108.7
H13A—C13A—H13B107.5H13C—C13B—H13D107.6
N14A—C14A—C13A112.0 (3)N14B—C14B—C13B111.4 (2)
N14A—C14A—H14A109.2N14B—C14B—H14F109.3
C13A—C14A—H14A109.2C13B—C14B—H14F109.3
N14A—C14A—H14B109.2N14B—C14B—H14G109.3
C13A—C14A—H14B109.2C13B—C14B—H14G109.3
H14A—C14A—H14B107.9H14F—C14B—H14G108.0
C14A—N14A—H14C109.5C14B—N14B—H14H109.5
C14A—N14A—H14D109.5C14B—N14B—H14I109.5
H14C—N14A—H14D109.5H14H—N14B—H14I109.5
C14A—N14A—H14E109.5C14B—N14B—H14J109.5
H14C—N14A—H14E109.5H14H—N14B—H14J109.5
H14D—N14A—H14E109.5H14I—N14B—H14J109.5
O15A—C15A—O16A124.1 (3)O16B—C15B—O15B124.7 (3)
O15A—C15A—C10A117.9 (2)O16B—C15B—C10B120.0 (3)
O16A—C15A—C10A117.9 (3)O15B—C15B—C10B115.2 (3)
C6A—N1A—C2A—O2A179.8 (3)C6B—N1B—C2B—O2B178.4 (3)
C7A—N1A—C2A—O2A0.2 (4)C7B—N1B—C2B—O2B2.0 (4)
C6A—N1A—C2A—N3A0.7 (4)C6B—N1B—C2B—N3B1.5 (4)
C7A—N1A—C2A—N3A179.0 (3)C7B—N1B—C2B—N3B178.2 (2)
O2A—C2A—N3A—C4A177.4 (3)O2B—C2B—N3B—C4B179.0 (3)
N1A—C2A—N3A—C4A1.7 (4)N1B—C2B—N3B—C4B1.1 (4)
C2A—N3A—C4A—N4A178.6 (3)C2B—N3B—C4B—N4B177.9 (2)
C2A—N3A—C4A—C5A2.5 (4)C2B—N3B—C4B—C5B2.8 (4)
N4A—C4A—C5A—C6A179.8 (3)N4B—C4B—C5B—C6B178.9 (3)
N3A—C4A—C5A—C6A0.9 (4)N3B—C4B—C5B—C6B1.8 (4)
C4A—C5A—C6A—N1A1.5 (4)C4B—C5B—C6B—N1B0.9 (4)
C2A—N1A—C6A—C5A2.3 (4)C2B—N1B—C6B—C5B2.5 (4)
C7A—N1A—C6A—C5A177.3 (3)C7B—N1B—C6B—C5B177.1 (3)
C6A—N1A—C7A—C8A102.4 (3)C6B—N1B—C7B—C8B104.6 (3)
C2A—N1A—C7A—C8A77.2 (3)C2B—N1B—C7B—C8B75.1 (3)
N1A—C7A—C8A—C9A57.6 (3)N1B—C7B—C8B—C9B56.5 (3)
C7A—C8A—C9A—O9A46.2 (4)C7B—C8B—C9B—O9B54.9 (4)
C7A—C8A—C9A—N10A133.1 (3)C7B—C8B—C9B—N10B124.6 (3)
O9A—C9A—N10A—C10A2.8 (4)O9B—C9B—N10B—C10B0.8 (4)
C8A—C9A—N10A—C10A176.5 (2)C8B—C9B—N10B—C10B179.7 (2)
C9A—N10A—C10A—C11A117.0 (3)C9B—N10B—C10B—C11B44.8 (4)
C9A—N10A—C10A—C15A114.4 (3)C9B—N10B—C10B—C15B84.7 (3)
N10A—C10A—C11A—C12A67.0 (3)N10B—C10B—C11B—C12B58.1 (3)
C15A—C10A—C11A—C12A165.9 (2)C15B—C10B—C11B—C12B171.3 (2)
C10A—C11A—C12A—C13A77.3 (3)C10B—C11B—C12B—C13B176.0 (2)
C11A—C12A—C13A—C14A72.9 (3)C11B—C12B—C13B—C14B75.1 (3)
C12A—C13A—C14A—N14A62.3 (3)C12B—C13B—C14B—N14B73.6 (3)
N10A—C10A—C15A—O15A153.2 (2)N10B—C10B—C15B—O16B8.4 (4)
C11A—C10A—C15A—O15A27.5 (4)C11B—C10B—C15B—O16B122.6 (3)
N10A—C10A—C15A—O16A30.2 (3)N10B—C10B—C15B—O15B168.4 (2)
C11A—C10A—C15A—O16A155.9 (2)C11B—C10B—C15B—O15B60.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4A—H4A1···N3Bi0.882.082.956 (4)173
N4A—H4A2···O16Ai0.882.142.857 (3)138
N10A—H10A···O2B0.882.062.907 (3)161
N14A—H14D···O15Bii0.911.862.769 (4)177
N14A—H14E···O9Aiii0.911.882.787 (4)176
N14A—H14C···O16Ai0.911.972.870 (4)168
N14A—H14C···O15Ai0.912.563.095 (3)118
N4B—H4B1···N3Aiv0.882.072.939 (4)171
N4B—H4B2···O16Biv0.882.152.876 (3)140
N10B—H10C···O2A0.881.952.796 (3)161
N14B—H14I···O15Av0.911.802.694 (3)165
N14B—H14H···O9Bvi0.911.952.842 (4)166
N14B—H14J···O15Biv0.912.292.988 (3)133
N14B—H14J···O16Biv0.912.102.987 (4)165
Symmetry codes: (i) x1, y1, z; (ii) x1, y, z1; (iii) x1, y, z; (iv) x+1, y+1, z; (v) x+1, y, z+1; (vi) x+1, y, z.

Experimental details

(I)(II)(III)
Crystal data
Chemical formulaC16H18N4O4C10H14N4O5·H2OC13H21N5O4
Mr330.34288.27311.35
Crystal system, space groupTriclinic, P1Triclinic, P1Triclinic, P1
Temperature (K)100100100
a, b, c (Å)9.3587 (12), 10.3445 (13), 16.925 (2)4.863 (1), 10.771 (2), 12.228 (2)6.9334 (9), 8.2977 (10), 13.2491 (16)
α, β, γ (°)92.079 (2), 95.775 (2), 95.245 (2)80.45 (3), 89.23 (3), 88.61 (3)90.780 (2), 93.498 (2), 107.293 (2)
V3)1621.7 (4)631.4 (2)726.02 (16)
Z422
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.100.130.11
Crystal size (mm)0.25 × 0.20 × 0.040.25 × 0.25 × 0.060.40 × 0.18 × 0.04
Data collection
DiffractometerBruker SMART APEX
diffractometer
Bruker SMART APEX
diffractometer
Bruker SMART APEX
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.832, 0.9980.827, 0.9930.878, 0.996
No. of measured, independent and
observed reflections
8913, 6059, 5788 [I > \2s(I)]3919, 2336, 2284 [I > 2σ(I)]7954, 2970, 2714 [I > 2σ(I)]
Rint0.0250.0220.025
(sin θ/λ)max1)0.6100.6100.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.150, 1.13 0.048, 0.114, 1.17 0.038, 0.100, 1.00
No. of reflections605923362970
No. of parameters896377399
No. of restraints18033
H-atom treatmentH-atom parameters constrainedH atoms treated by a mixture of independent and constrained refinementH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.310.32, 0.250.34, 0.19

Computer programs: SMART (Bruker, 1998), SMART, SAINT-Plus (Bruker, 1998), SHELXD (Sheldrick, 1990b), SHELXS97 (Sheldrick, 1990a), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2001), Mercury (Bruno et al., 2002).

Selected torsion angles (º) for (I) top
C2A—N1A—C7A—C8A74.4 (5)C2C—N1C—C7C—C8C78.4 (5)
N1A—C7A—C8A—C9A66.3 (5)N1C—C7C—C8C—C9C61.1 (5)
C7A—C8A—C9A—N10A150.0 (4)C7C—C8C—C9C—N10C124.4 (5)
C8A—C9A—N10A—C10A178.8 (4)C8C—C9C—N10C—C10C179.2 (4)
C9A—N10A—C10A—C11A135.4 (5)C9C—N10C—C10C—C11C164.5 (4)
N10A—C10A—C11A—C12A53.9 (6)N10C—C10C—C11C—C12C71.6 (5)
C10A—C11A—C12A—C13A47.3 (8)C10C—C11C—C12C—C13C92.9 (4)
C2B—N1B—C7B—C8B78.4 (5)C2D—N1D—C7D—C8D80.6 (5)
N1B—C7B—C8B—C9B61.7 (5)N1D—C7D—C8D—C9D64.2 (5)
C7B—C8B—C9B—N10B148.0 (4)C7D—C8D—C9D—N10D124.2 (4)
C8B—C9B—N10B—C10B179.9 (4)C8D—C9D—N10D—C10D178.4 (4)
C9B—N10B—C10B—C11B141.4 (5)C9D—N10D—C10D—C11D163.8 (4)
N10B—C10B—C11B—C12B63.7 (6)N10D—C10D—C11D—C12D59.8 (6)
C10B—C11B—C12B—C13B24.7 (7)C10D—C11D—C12D—C13D99.0 (6)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N3A—H3A···O18Di0.881.752.623 (6)171
N4A—H4AA···O19Di0.881.942.811 (7)173
N10A—H10A···O19Cii0.882.193.036 (6)161
N3B—H3B···O18Ciii0.881.732.565 (6)159
N4B—H4AB···O19Ciii0.882.142.965 (7)156
N4B—H4BB···O2Aiv0.882.422.934 (7)118
N10B—H10B···O19Di0.882.052.885 (6)159
N3C—H3C···O19B0.881.742.601 (5)167
N4C—H4AC···O18B0.882.052.903 (6)164
N4C—H4BC···O19Av0.882.283.090 (7)154
N10C—H10C···O18Avi0.882.032.890 (5)167
N3D—H3D···O19Avi0.881.752.615 (5)168
N4D—H4AD···O18Avi0.882.062.920 (6)165
N4D—H4BD···O19B0.882.233.047 (6)155
N10D—H10D···O18Biv0.882.102.945 (5)162
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z1; (iii) x+1, y, z1; (iv) x, y1, z; (v) x1, y, z+1; (vi) x1, y1, z+1.
Selected torsion angles (º) for (II) top
C2A—N1A—C7A—C8A74.2 (4)C2B—N1B—C7B—C8B80.8 (4)
N1A—C7A—C8A—C9A178.1 (3)N1B—C7B—C8B—C9B179.9 (3)
C7A—C8A—C9A—N10A159.2 (3)C7B—C8B—C9B—N10B160.2 (4)
C8A—C9A—N10A—C10A177.3 (3)C8B—C9B—N10B—C10B179.8 (3)
C9A—N10A—C10A—C11A157.7 (4)C9B—N10B—C10B—C11B67.9 (5)
N10A—C10A—C11A—O11A62.5 (5)N10B—C10B—C11B—O11B59.8 (5)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N3A—H3A···O13Ai0.881.882.747 (4)167
N4A—H4AA···O12Ai0.881.932.805 (5)170
N4A—H4BA···O13Bii0.882.062.928 (5)168
N10A—H10A···O9Aiii0.882.122.975 (5)163
O11A—H11A···O12B0.841.932.704 (5)153
N3B—H3B···O13Biv0.881.892.759 (4)168
N4B—H4AB···O12Biv0.881.912.789 (5)174
N4B—H4BB···O13Av0.882.082.960 (5)175
N10B—H10B···O9Bvi0.882.203.000 (5)150
O11B—H11B···O12Avii0.842.012.759 (4)148
O1C—H1C···O11Avi0.93 (5)1.96 (6)2.841 (5)159 (5)
O1C—H2C···O9A0.88 (6)2.07 (6)2.909 (4)158 (6)
O1D—H1D···O11B0.91 (8)2.05 (8)2.851 (5)146 (7)
O1D—H2D···O9Bvi0.80 (7)2.17 (7)2.951 (4)164 (7)
Symmetry codes: (i) x+1, y1, z; (ii) x, y1, z1; (iii) x+1, y, z; (iv) x1, y1, z; (v) x, y1, z; (vi) x1, y, z; (vii) x, y, z+1.
Selected torsion angles (º) for (III) top
C2A—N1A—C7A—C8A77.2 (3)C2B—N1B—C7B—C8B75.1 (3)
N1A—C7A—C8A—C9A57.6 (3)N1B—C7B—C8B—C9B56.5 (3)
C7A—C8A—C9A—N10A133.1 (3)C7B—C8B—C9B—N10B124.6 (3)
C8A—C9A—N10A—C10A176.5 (2)C8B—C9B—N10B—C10B179.7 (2)
C9A—N10A—C10A—C11A117.0 (3)C9B—N10B—C10B—C11B44.8 (4)
N10A—C10A—C11A—C12A67.0 (3)N10B—C10B—C11B—C12B58.1 (3)
C10A—C11A—C12A—C13A77.3 (3)C10B—C11B—C12B—C13B176.0 (2)
C11A—C12A—C13A—C14A72.9 (3)C11B—C12B—C13B—C14B75.1 (3)
C12A—C13A—C14A—N14A62.3 (3)C12B—C13B—C14B—N14B73.6 (3)
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
N4A—H4A1···N3Bi0.882.082.956 (4)173
N4A—H4A2···O16Ai0.882.142.857 (3)138
N10A—H10A···O2B0.882.062.907 (3)161
N14A—H14D···O15Bii0.911.862.769 (4)177
N14A—H14E···O9Aiii0.911.882.787 (4)176
N14A—H14C···O16Ai0.911.972.870 (4)168
N14A—H14C···O15Ai0.912.563.095 (3)118
N4B—H4B1···N3Aiv0.882.072.939 (4)171
N4B—H4B2···O16Biv0.882.152.876 (3)140
N10B—H10C···O2A0.881.952.796 (3)161
N14B—H14I···O15Av0.911.802.694 (3)165
N14B—H14H···O9Bvi0.911.952.842 (4)166
N14B—H14J···O15Biv0.912.292.988 (3)133
N14B—H14J···O16Biv0.912.102.987 (4)165
Symmetry codes: (i) x1, y1, z; (ii) x1, y, z1; (iii) x1, y, z; (iv) x+1, y+1, z; (v) x+1, y, z+1; (vi) x+1, y, z.
The geometrical classification for side-chain poition of cytosine hybrid dipeptide top
Compound(I)1)(II)1)(III)1)(IV)(V)(VI)(VII)(VIII)
Amino acidL-PheL-SerL-LysL-TyrL-ThrL-TrpL-IleL-Ala
PositionO+O+S–
1) the present structures.
 

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