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The tartaric acid complexes with arginine and lysine exhibit two stoichiometries depending upon the ionization state of the anion. The structures reported here are DL-argininium DL-hydrogen tartrate, bis(L-argininium) L-tartrate, bis(DL-lysinium) DL-tartrate monohydrate, L-lysinium D-hydrogen tartrate and L-lysinium L-hydrogen tartrate. During crystallization, L-lysine preferentially interacts with D-tartaric acid to form a complex when DL-tartaric acid is used in the experiment. The anions and the cations aggregate into separate alternating layers in four of the five complexes. In bis(L-argininium) L-tartrate, the amino acid layers are interconnected by individual tartrate ions which do not interact among themselves. The aggregation of argininium ions in the DL- and the L-arginine complexes is remarkably similar, which is in turn similar to those observed in other dicarboxylic acid complexes of arginine. Thus, argininium ions have a tendency to assume similar patterns of aggregation, which are largely unaffected by a change in the chemistry of partner molecules such as the introduction of hydroxyl groups or a change in chirality or stoichiometry. On the contrary, the lysinium ions exhibit fundamentally different aggregation patterns in the DL-DL complexes on the one hand and L-D and L-L complexes on the other. Interestingly, the pattern in the L-D complex is similar to that in the L-L complex. The lysinium ions in the DL-DL complex exhibit an aggregation pattern similar to those observed in the DL-lysine complexes involving other dicarboxylic acids. Thus, the effect of change in the chirality of a subset of the component complexes could be profound or marginal, in an unpredictable manner. The relevant crystal structures appear to indicate that the preference of L-lysine for D-tartaric acid is perhaps caused by chiral discrimination resulting from the amplification of a small energy difference.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810701107X/bk5044sup1.cif
Contains datablocks I, II, III, IV, V

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810701107X/bk5044Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810701107X/bk5044IIsup3.hkl
Contains datablock st2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810701107X/bk5044IIIsup4.hkl
Contains datablock st3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810701107X/bk5044IVsup5.hkl
Contains datablock dis

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810701107X/bk5044Vsup6.hkl
Contains datablock V

CCDC references: 650652; 650653; 650654; 650655; 650656

Computing details top

For all compounds, data collection: Bruker SMART; cell refinement: Bruker SMART; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and pyMOL (DeLano, 2002); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
(I) DL-arginine DL-tartaric acid complex top
Crystal data top
C6H15N4O2+·C4H5O6Z = 2
Mr = 324.30F(000) = 344
Triclinic, P1Dx = 1.508 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.4876 (16) ÅCell parameters from 835 reflections
b = 10.021 (3) Åθ = 1.6–22.0°
c = 13.868 (4) ŵ = 0.13 mm1
α = 109.079 (5)°T = 298 K
β = 94.378 (5)°Plate, colourless
γ = 94.538 (5)°0.25 × 0.2 × 0.1 mm
V = 714.3 (4) Å3
Data collection top
Bruker SMART CCD area detector
diffractometer
1543 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.057
Graphite monochromatorθmax = 25.0°, θmin = 1.6°
ϕ and ω scanh = 66
6914 measured reflectionsk = 1111
2504 independent reflectionsl = 1616
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0496P)2 + 0.0651P]
where P = (Fo2 + 2Fc2)/3
2508 reflections(Δ/σ)max < 0.001
260 parametersΔρmax = 0.27 e Å3
52 restraintsΔρmin = 0.23 e Å3
Crystal data top
C6H15N4O2+·C4H5O6γ = 94.538 (5)°
Mr = 324.30V = 714.3 (4) Å3
Triclinic, P1Z = 2
a = 5.4876 (16) ÅMo Kα radiation
b = 10.021 (3) ŵ = 0.13 mm1
c = 13.868 (4) ÅT = 298 K
α = 109.079 (5)°0.25 × 0.2 × 0.1 mm
β = 94.378 (5)°
Data collection top
Bruker SMART CCD area detector
diffractometer
1543 reflections with I > 2σ(I)
6914 measured reflectionsRint = 0.057
2504 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06252 restraints
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.27 e Å3
2508 reflectionsΔρmin = 0.23 e Å3
260 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*/UeqOcc. (<1)
O10.2455 (4)0.5905 (3)1.06068 (17)0.0411 (7)
O20.4559 (5)0.7503 (3)1.02198 (19)0.0514 (8)
N10.2269 (6)0.4379 (3)0.8647 (3)0.0343 (8)
C10.3313 (7)0.6486 (4)1.0000 (3)0.0342 (9)
C20.2778 (7)0.5878 (3)0.8884 (3)0.0362 (9)
H20.41740.59400.84220.043*
C3A0.0414 (7)0.6684 (4)0.8713 (3)0.0310 (11)0.824 (5)
H310.08620.68060.92680.037*0.824 (5)
H320.01740.61400.80740.037*0.824 (5)
C4A0.0980 (8)0.8141 (4)0.8672 (4)0.0404 (12)0.824 (5)
H410.17450.86370.92760.048*0.824 (5)
H420.21260.80130.80720.048*0.824 (5)
C3B0.191 (3)0.7027 (16)0.8434 (13)0.036 (3)0.176 (5)
H330.30880.77180.85220.043*0.176 (5)
H340.17950.65950.77050.043*0.176 (5)
C4B0.062 (3)0.7771 (14)0.8984 (14)0.043 (4)0.176 (5)
H430.18380.70990.88350.051*0.176 (5)
H440.05500.81110.97210.051*0.176 (5)
C50.1386 (7)0.9033 (4)0.8623 (3)0.0492 (11)
H5A0.10561.00060.87340.059*
H5B0.26250.90370.91610.059*
N60.2305 (6)0.8457 (3)0.7630 (2)0.0409 (8)
C70.4125 (6)0.9127 (3)0.7339 (3)0.0319 (8)
N80.5122 (6)1.0401 (3)0.7914 (3)0.0436 (9)
N90.4972 (7)0.8496 (4)0.6445 (3)0.0482 (10)
O110.0430 (4)0.1521 (3)0.74693 (17)0.0411 (7)
O120.0821 (5)0.0195 (2)0.58267 (17)0.0437 (7)
C130.0104 (6)0.1294 (3)0.6593 (3)0.0285 (8)
C140.1883 (6)0.2390 (3)0.6389 (2)0.0256 (8)
H140.30600.18960.59400.031*
O150.3187 (4)0.3330 (2)0.73050 (18)0.0363 (6)
C160.0435 (6)0.3222 (3)0.5845 (2)0.0300 (8)
H160.02340.25840.51600.036*
O170.1547 (5)0.3708 (3)0.6421 (2)0.0421 (7)
C180.2080 (7)0.4443 (4)0.5737 (2)0.0333 (9)
O190.1640 (5)0.5675 (2)0.60692 (18)0.0459 (7)
O200.3959 (5)0.4042 (2)0.52453 (19)0.0472 (7)
H1A0.055 (9)0.431 (4)0.902 (3)0.074 (14)*
H1B0.220 (7)0.399 (4)0.803 (3)0.050 (12)*
H1C0.365 (11)0.387 (5)0.892 (4)0.118 (19)*
H60.168 (9)0.766 (5)0.724 (3)0.078 (16)*
H8A0.450 (7)1.094 (4)0.853 (3)0.065 (13)*
H8B0.651 (8)1.080 (4)0.774 (3)0.057 (12)*
H9A0.618 (7)0.893 (4)0.628 (3)0.045 (12)*
H9B0.445 (7)0.758 (4)0.611 (3)0.054 (12)*
H120.00000.00000.50000.11 (2)*
H150.244 (9)0.326 (5)0.785 (3)0.103 (19)*
H170.278 (6)0.380 (5)0.609 (3)0.078 (17)*
H200.50000.50000.50000.12 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0400 (16)0.0502 (16)0.0269 (14)0.0064 (12)0.0063 (12)0.0066 (12)
O20.0517 (18)0.0457 (17)0.0461 (17)0.0105 (14)0.0163 (14)0.0026 (13)
N10.034 (2)0.0391 (19)0.0218 (17)0.0022 (15)0.0081 (16)0.0009 (15)
C10.032 (2)0.033 (2)0.029 (2)0.0128 (17)0.0088 (17)0.0003 (18)
C20.048 (2)0.028 (2)0.0281 (19)0.0039 (17)0.0091 (17)0.0045 (16)
C3A0.032 (3)0.033 (2)0.030 (2)0.007 (2)0.014 (2)0.0104 (19)
C4A0.038 (3)0.039 (3)0.049 (3)0.005 (2)0.013 (2)0.019 (2)
C3B0.039 (6)0.032 (6)0.036 (6)0.012 (6)0.010 (6)0.008 (5)
C4B0.040 (6)0.042 (6)0.041 (6)0.002 (6)0.015 (6)0.005 (6)
C50.058 (3)0.037 (2)0.046 (2)0.010 (2)0.025 (2)0.0034 (19)
N60.047 (2)0.0312 (19)0.0366 (19)0.0121 (16)0.0156 (16)0.0024 (16)
C70.034 (2)0.027 (2)0.032 (2)0.0021 (16)0.0062 (17)0.0065 (16)
N80.044 (2)0.0290 (18)0.049 (2)0.0086 (16)0.0234 (17)0.0002 (16)
N90.062 (3)0.033 (2)0.041 (2)0.0107 (18)0.0239 (18)0.0002 (17)
O110.0449 (16)0.0461 (15)0.0306 (14)0.0101 (12)0.0141 (12)0.0117 (12)
O120.0581 (18)0.0310 (14)0.0339 (15)0.0142 (12)0.0142 (13)0.0024 (12)
C130.0274 (19)0.0270 (19)0.033 (2)0.0031 (15)0.0082 (16)0.0116 (16)
C140.0242 (18)0.0266 (18)0.0263 (18)0.0008 (15)0.0078 (15)0.0087 (15)
O150.0351 (15)0.0453 (15)0.0236 (13)0.0118 (11)0.0019 (11)0.0098 (12)
C160.033 (2)0.032 (2)0.0212 (17)0.0000 (16)0.0043 (15)0.0039 (15)
O170.0283 (15)0.0570 (18)0.0421 (16)0.0113 (13)0.0048 (13)0.0164 (13)
C180.050 (2)0.026 (2)0.0233 (18)0.0014 (18)0.0027 (17)0.0080 (15)
O190.0632 (19)0.0235 (15)0.0461 (16)0.0031 (13)0.0116 (14)0.0040 (12)
O200.0643 (19)0.0348 (15)0.0523 (16)0.0094 (13)0.0333 (15)0.0210 (13)
Geometric parameters (Å, º) top
O1—C11.254 (4)C5—H5B0.9700
O2—C11.240 (4)N6—C71.320 (4)
N1—C21.483 (5)N6—H60.84 (4)
N1—H1A1.06 (5)C7—N81.313 (4)
N1—H1B0.82 (4)C7—N91.332 (4)
N1—H1C1.04 (6)N8—H8A0.96 (4)
C1—C21.527 (5)N8—H8B0.92 (4)
C2—C3B1.540 (5)N9—H9A0.85 (4)
C2—C3A1.549 (4)N9—H9B0.89 (4)
C2—H20.9800O11—C131.224 (4)
C3A—C4A1.534 (4)O12—C131.290 (4)
C3A—H310.9700O12—H121.225
C3A—H320.9700C13—C141.522 (4)
C4A—C51.536 (4)C14—O151.409 (4)
C4A—H410.9700C14—C161.523 (5)
C4A—H420.9700C14—H140.9800
C3B—C4B1.540 (5)O15—H150.91 (5)
C3B—H330.9700C16—O171.422 (4)
C3B—H340.9700C16—C181.517 (5)
C4B—C51.546 (5)C16—H160.9800
C4B—H430.9700O17—H170.82 (2)
C4B—H440.9700C18—O191.219 (4)
C5—N61.454 (4)C18—O201.298 (4)
C5—H5A0.9700O20—H201.233
C2—N1—H1A111 (2)N6—C5—C4A110.6 (3)
C2—N1—H1B111 (3)N6—C5—C4B107.6 (8)
H1A—N1—H1B106 (3)N6—C5—H5A109.5
C2—N1—H1C107 (3)C4A—C5—H5A109.5
H1A—N1—H1C109 (3)N6—C5—H5B109.5
H1B—N1—H1C112 (4)C4A—C5—H5B109.5
O2—C1—O1126.1 (3)C4B—C5—H5B72.1
O2—C1—C2117.1 (4)H5A—C5—H5B108.1
O1—C1—C2116.8 (3)C7—N6—C5122.7 (3)
N1—C2—C1109.9 (3)C7—N6—H6119 (3)
N1—C2—C3B131.6 (8)C5—N6—H6118 (3)
C1—C2—C3B113.3 (8)N8—C7—N6121.3 (3)
N1—C2—C3A105.9 (3)N8—C7—N9119.3 (3)
C1—C2—C3A110.3 (3)N6—C7—N9119.4 (3)
N1—C2—H2110.2C7—N8—H8A123 (2)
C1—C2—H2110.2C7—N8—H8B120 (2)
C3B—C2—H274.0H8A—N8—H8B117 (3)
C3A—C2—H2110.2C7—N9—H9A118 (2)
C4A—C3A—C2109.4 (3)C7—N9—H9B118 (2)
C4A—C3A—H31109.8H9A—N9—H9B123 (3)
C2—C3A—H31109.8C13—O12—H12118.3
C4A—C3A—H32109.8O11—C13—O12123.4 (3)
C2—C3A—H32109.8O11—C13—C14118.4 (3)
H31—C3A—H32108.2O12—C13—C14118.2 (3)
C3A—C4A—C5110.6 (3)O15—C14—C13111.6 (2)
C3A—C4A—H41109.5O15—C14—C16109.7 (3)
C5—C4A—H41109.5C13—C14—C16108.8 (3)
C3A—C4A—H42109.5O15—C14—H14108.9
C5—C4A—H42109.5C13—C14—H14108.9
H41—C4A—H42108.1C16—C14—H14108.9
C2—C3B—C4B109.5 (8)C14—O15—H15110 (3)
C2—C3B—H33109.8O17—C16—C18111.7 (3)
C4B—C3B—H33109.8O17—C16—C14107.7 (3)
C2—C3B—H34109.8C18—C16—C14110.7 (3)
C4B—C3B—H34109.8O17—C16—H16108.9
H33—C3B—H34108.2C18—C16—H16108.9
C3B—C4B—C5110.0 (8)C14—C16—H16108.9
C3B—C4B—H43109.7C16—O17—H17115 (3)
C5—C4B—H43109.7O19—C18—O20123.8 (3)
C3B—C4B—H44109.7O19—C18—C16122.8 (3)
C5—C4B—H44109.7O20—C18—C16113.4 (3)
H43—C4B—H44108.2C18—O20—H20112.0
O2—C1—C2—N1155.9 (3)C4B—C5—N6—C7145.1 (7)
O1—C1—C2—N124.0 (4)C5—N6—C7—N84.0 (6)
O2—C1—C2—C3B46.6 (8)C5—N6—C7—N9175.9 (4)
O1—C1—C2—C3B133.6 (8)O11—C13—C14—O1516.5 (4)
O2—C1—C2—C3A87.8 (4)O12—C13—C14—O15165.6 (3)
O1—C1—C2—C3A92.4 (4)O11—C13—C14—C16104.7 (3)
N1—C2—C3A—C4A165.7 (3)O12—C13—C14—C1673.2 (4)
C1—C2—C3A—C4A75.5 (4)O15—C14—C16—O1771.5 (3)
C2—C3A—C4A—C5173.7 (3)C13—C14—C16—O1750.8 (3)
N1—C2—C3B—C4B84.8 (16)O15—C14—C16—C1850.9 (3)
C1—C2—C3B—C4B66.5 (16)C13—C14—C16—C18173.3 (3)
C2—C3B—C4B—C5173.9 (11)O17—C16—C18—O193.3 (5)
C3A—C4A—C5—N670.5 (5)C14—C16—C18—O19123.4 (3)
C3B—C4B—C5—N679.1 (15)O17—C16—C18—O20177.8 (3)
C4A—C5—N6—C7170.9 (4)C14—C16—C18—O2057.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i1.06 (5)1.74 (5)2.788 (4)169 (3)
N1—H1B···O170.82 (4)2.21 (4)3.001 (4)160 (3)
N1—H1C···O1ii1.04 (6)2.29 (6)3.171 (4)141 (4)
N1—H1C···O2ii1.04 (6)2.31 (6)3.300 (4)159 (4)
N6—H6···O190.84 (4)2.11 (4)2.892 (4)155 (4)
N8—H8A···O2iii0.96 (4)1.91 (4)2.807 (4)155 (3)
N8—H8B···O11iv0.92 (4)1.89 (4)2.801 (4)174 (4)
N9—H9A···O12iv0.85 (4)2.25 (4)3.099 (4)176 (3)
N9—H9B···O190.89 (4)2.34 (4)3.111 (5)145 (3)
N9—H9B···O20v0.89 (4)2.33 (4)2.976 (4)129 (3)
O12—H12···O12vi1.231.232.451 (4)180
O15—H15···O1i0.91 (5)2.02 (5)2.813 (3)144 (4)
O17—H17···O20vii0.822.132.953 (4)178
O20—H20···O20v1.231.232.466 (4)180
Symmetry codes: (i) x, y+1, z+2; (ii) x1, y+1, z+2; (iii) x, y+2, z+2; (iv) x+1, y+1, z; (v) x+1, y+1, z+1; (vi) x, y, z+1; (vii) x1, y, z.
(II) L-arginine L-tartaric acid complex top
Crystal data top
2(C6H15N4O2)+·C4H4O62F(000) = 532
Mr = 498.51Dx = 1.440 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1374 reflections
a = 9.907 (2) Åθ = 1.5–25.0°
b = 8.7428 (18) ŵ = 0.12 mm1
c = 14.076 (3) ÅT = 298 K
β = 109.412 (3)°Plate, colourless
V = 1149.9 (4) Å30.42 × 0.27 × 0.15 mm
Z = 2
Data collection top
Bruker SMART CCD area detector
diffractometer
2054 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
Graphite monochromatorθmax = 25.0°, θmin = 1.5°
ϕ and ω scanh = 1111
8353 measured reflectionsk = 109
2162 independent reflectionsl = 1616
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)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.0559P)2 + 0.2589P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2162 reflectionsΔρmax = 0.37 e Å3
380 parametersΔρmin = 0.17 e Å3
2 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0074 (19)
Crystal data top
2(C6H15N4O2)+·C4H4O62V = 1149.9 (4) Å3
Mr = 498.51Z = 2
Monoclinic, P21Mo Kα radiation
a = 9.907 (2) ŵ = 0.12 mm1
b = 8.7428 (18) ÅT = 298 K
c = 14.076 (3) Å0.42 × 0.27 × 0.15 mm
β = 109.412 (3)°
Data collection top
Bruker SMART CCD area detector
diffractometer
2054 reflections with I > 2σ(I)
8353 measured reflectionsRint = 0.016
2162 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0342 restraints
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.37 e Å3
2162 reflectionsΔρmin = 0.17 e Å3
380 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
O10.6385 (2)0.3214 (2)0.80456 (14)0.0372 (5)
O20.4988 (2)0.5225 (3)0.79604 (15)0.0513 (6)
N10.5701 (2)0.2930 (3)0.60514 (16)0.0281 (5)
C10.5556 (3)0.4243 (3)0.75787 (18)0.0292 (5)
C20.5218 (3)0.4347 (3)0.64353 (18)0.0272 (5)
H20.57670.52050.63040.033*
C30.3639 (3)0.4659 (3)0.58693 (18)0.0319 (6)
H3A0.33590.55940.61250.038*
H3B0.35070.48140.51620.038*
C40.2674 (3)0.3360 (4)0.5972 (2)0.0411 (7)
H4A0.27120.25430.55150.049*
H4B0.30430.29580.66520.049*
C50.1129 (3)0.3821 (5)0.5754 (2)0.0437 (8)
H5A0.06170.29900.59390.052*
H5B0.10880.47030.61610.052*
N60.0434 (2)0.4192 (3)0.46961 (17)0.0386 (6)
C70.0955 (3)0.4425 (4)0.4291 (2)0.0343 (6)
N80.1806 (3)0.4440 (4)0.4843 (2)0.0475 (7)
N90.1526 (3)0.4666 (4)0.33043 (18)0.0439 (7)
O110.8614 (2)0.2550 (3)0.69469 (15)0.0465 (6)
O120.9239 (3)0.4992 (3)0.70440 (18)0.0654 (8)
N110.9510 (3)0.2266 (4)0.89608 (18)0.0351 (6)
C110.9236 (3)0.3724 (4)0.7406 (2)0.0428 (8)
C121.0153 (3)0.3497 (4)0.8512 (2)0.0377 (7)
H121.02220.44540.88880.045*
C131.1643 (3)0.3000 (4)0.8503 (2)0.0413 (7)
H13A1.15290.20960.80830.050*
H13B1.20230.38060.81900.050*
C141.2733 (3)0.2651 (4)0.9523 (2)0.0435 (7)
H14A1.23780.18440.98510.052*
H14B1.29010.35540.99460.052*
C151.4115 (3)0.2148 (5)0.9375 (2)0.0497 (8)
H15A1.39360.12720.89280.060*
H15B1.44860.29710.90700.060*
N161.5155 (3)0.1749 (4)1.03412 (18)0.0466 (7)
C171.6460 (3)0.2285 (4)1.0709 (2)0.0359 (6)
N181.7052 (3)0.3150 (4)1.0187 (2)0.0445 (7)
N191.7213 (3)0.1958 (4)1.1672 (2)0.0529 (8)
O210.4623 (2)0.0132 (3)0.66299 (17)0.0444 (5)
O220.5159 (2)0.2058 (3)0.60332 (15)0.0441 (5)
C230.5371 (3)0.1060 (3)0.66868 (19)0.0305 (6)
C240.6650 (3)0.1278 (3)0.76652 (18)0.0290 (6)
H240.64540.21620.80270.035*
O250.6877 (2)0.0017 (2)0.83055 (14)0.0365 (5)
C260.7999 (3)0.1605 (3)0.74077 (18)0.0302 (6)
H260.78830.26060.70770.036*
O270.8179 (2)0.0494 (3)0.67198 (14)0.0387 (5)
C280.9295 (3)0.1695 (3)0.83744 (19)0.0322 (6)
O291.0307 (2)0.0753 (3)0.84651 (17)0.0479 (6)
O300.9270 (2)0.2697 (3)0.89899 (14)0.0436 (5)
H1A0.527 (3)0.211 (4)0.619 (2)0.028 (7)*
H1B0.669 (4)0.278 (5)0.634 (2)0.048 (9)*
H1C0.545 (3)0.298 (4)0.537 (2)0.035 (8)*
H60.101 (3)0.418 (4)0.432 (2)0.042 (9)*
H8A0.148 (4)0.445 (5)0.546 (3)0.045 (9)*
H8B0.269 (4)0.445 (4)0.454 (2)0.032 (8)*
H9A0.100 (4)0.458 (5)0.293 (3)0.060 (11)*
H9B0.246 (4)0.480 (5)0.309 (3)0.058 (11)*
H11A0.862 (4)0.238 (5)0.875 (3)0.050 (10)*
H11B0.988 (3)0.217 (4)0.966 (2)0.043 (9)*
H11C0.977 (4)0.134 (5)0.878 (3)0.055 (11)*
H161.495 (3)0.116 (4)1.080 (2)0.037 (8)*
H18A1.670 (3)0.326 (4)0.952 (3)0.045 (9)*
H18B1.802 (4)0.352 (5)1.058 (3)0.053 (10)*
H19A1.676 (3)0.141 (5)1.202 (3)0.049 (9)*
H19B1.816 (5)0.213 (6)1.184 (3)0.082 (14)*
H250.627 (3)0.067 (4)0.802 (2)0.051 (11)*
H270.841 (4)0.040 (6)0.698 (3)0.054 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0387 (10)0.0469 (12)0.0238 (9)0.0092 (10)0.0073 (8)0.0036 (9)
O20.0635 (14)0.0573 (15)0.0324 (11)0.0204 (12)0.0149 (10)0.0043 (10)
N10.0258 (11)0.0335 (13)0.0228 (11)0.0013 (10)0.0054 (9)0.0011 (10)
C10.0262 (11)0.0341 (14)0.0254 (12)0.0020 (12)0.0061 (10)0.0014 (11)
C20.0262 (12)0.0276 (13)0.0260 (12)0.0007 (11)0.0063 (10)0.0016 (10)
C30.0306 (13)0.0355 (15)0.0260 (13)0.0036 (12)0.0046 (10)0.0032 (11)
C40.0268 (14)0.0496 (19)0.0441 (17)0.0047 (13)0.0081 (12)0.0134 (14)
C50.0268 (13)0.069 (2)0.0345 (15)0.0055 (14)0.0097 (11)0.0151 (16)
N60.0248 (10)0.0620 (17)0.0294 (11)0.0048 (12)0.0095 (9)0.0076 (12)
C70.0273 (12)0.0422 (16)0.0323 (14)0.0010 (12)0.0085 (11)0.0025 (13)
N80.0216 (11)0.087 (2)0.0309 (13)0.0034 (14)0.0052 (10)0.0097 (14)
N90.0341 (13)0.0660 (19)0.0284 (12)0.0022 (13)0.0062 (10)0.0024 (13)
O110.0364 (10)0.0700 (17)0.0285 (10)0.0032 (11)0.0048 (9)0.0009 (11)
O120.102 (2)0.0561 (15)0.0474 (13)0.0320 (15)0.0369 (14)0.0156 (12)
N110.0247 (12)0.0541 (17)0.0238 (12)0.0006 (11)0.0045 (9)0.0020 (11)
C110.0423 (16)0.055 (2)0.0377 (16)0.0255 (16)0.0227 (13)0.0132 (16)
C120.0337 (14)0.0401 (16)0.0348 (15)0.0045 (13)0.0055 (12)0.0024 (13)
C130.0375 (15)0.0504 (18)0.0354 (15)0.0042 (14)0.0114 (12)0.0021 (14)
C140.0368 (15)0.055 (2)0.0376 (16)0.0000 (14)0.0104 (13)0.0020 (14)
C150.0295 (14)0.073 (2)0.0467 (17)0.0026 (15)0.0121 (13)0.0046 (17)
N160.0369 (13)0.0676 (19)0.0345 (13)0.0149 (13)0.0108 (11)0.0080 (13)
C170.0360 (14)0.0428 (16)0.0286 (13)0.0071 (13)0.0106 (11)0.0039 (12)
N180.0348 (13)0.0676 (19)0.0282 (13)0.0163 (13)0.0069 (10)0.0008 (13)
N190.0464 (15)0.070 (2)0.0355 (14)0.0186 (15)0.0041 (12)0.0059 (14)
O210.0260 (9)0.0392 (12)0.0571 (13)0.0015 (9)0.0009 (9)0.0086 (10)
O220.0497 (12)0.0426 (12)0.0285 (10)0.0086 (10)0.0025 (9)0.0001 (10)
C230.0249 (12)0.0323 (14)0.0297 (13)0.0044 (11)0.0031 (10)0.0072 (12)
C240.0278 (13)0.0340 (13)0.0217 (12)0.0018 (11)0.0037 (10)0.0015 (11)
O250.0354 (10)0.0408 (12)0.0280 (10)0.0070 (9)0.0034 (8)0.0069 (9)
C260.0321 (13)0.0350 (15)0.0217 (12)0.0029 (12)0.0068 (10)0.0034 (11)
O270.0406 (11)0.0524 (13)0.0243 (9)0.0025 (10)0.0123 (8)0.0012 (10)
C280.0283 (13)0.0409 (16)0.0250 (13)0.0099 (12)0.0058 (10)0.0055 (12)
O290.0295 (10)0.0553 (14)0.0489 (12)0.0007 (11)0.0005 (9)0.0013 (11)
O300.0434 (12)0.0530 (13)0.0265 (10)0.0083 (10)0.0010 (9)0.0030 (10)
Geometric parameters (Å, º) top
O1—C11.248 (3)C12—C131.544 (4)
O2—C11.242 (3)C12—H120.9800
N1—C21.493 (4)C13—C141.513 (4)
N1—H1A0.89 (4)C13—H13A0.9700
N1—H1B0.94 (3)C13—H13B0.9700
N1—H1C0.91 (3)C14—C151.517 (4)
C1—C21.534 (3)C14—H14A0.9700
C2—C31.525 (3)C14—H14B0.9700
C2—H20.9800C15—N161.450 (4)
C3—C41.523 (4)C15—H15A0.9700
C3—H3A0.9700C15—H15B0.9700
C3—H3B0.9700N16—C171.310 (4)
C4—C51.512 (4)N16—H160.89 (3)
C4—H4A0.9700C17—N181.321 (4)
C4—H4B0.9700C17—N191.343 (4)
C5—N61.454 (4)N18—H18A0.89 (3)
C5—H5A0.9700N18—H18B0.99 (4)
C5—H5B0.9700N19—H19A0.90 (4)
N6—C71.319 (3)N19—H19B0.90 (5)
N6—H60.90 (3)O21—C231.265 (4)
C7—N81.323 (4)O22—C231.234 (4)
C7—N91.331 (4)C23—C241.542 (3)
N8—H8A0.82 (4)C24—O251.417 (3)
N8—H8B0.84 (3)C24—C261.524 (3)
N9—H9A0.86 (4)C24—H240.9800
N9—H9B0.88 (4)O25—H250.83 (2)
O11—C111.260 (4)C26—O271.424 (3)
O12—C111.221 (4)C26—C281.531 (3)
N11—C121.494 (4)C26—H260.9800
N11—H11A0.84 (4)O27—H270.86 (5)
N11—H11B0.93 (3)C28—O301.238 (4)
N11—H11C0.92 (5)C28—O291.271 (4)
C11—C121.532 (4)
C2—N1—H1A110.5 (19)N11—C12—C13110.2 (3)
C2—N1—H1B112 (2)C11—C12—C13105.9 (2)
H1A—N1—H1B108 (3)N11—C12—H12110.5
C2—N1—H1C110 (2)C11—C12—H12110.5
H1A—N1—H1C107 (3)C13—C12—H12110.5
H1B—N1—H1C110 (3)C14—C13—C12115.6 (2)
O2—C1—O1125.7 (2)C14—C13—H13A108.4
O2—C1—C2116.1 (2)C12—C13—H13A108.4
O1—C1—C2118.1 (2)C14—C13—H13B108.4
N1—C2—C3110.8 (2)C12—C13—H13B108.4
N1—C2—C1110.2 (2)H13A—C13—H13B107.5
C3—C2—C1112.8 (2)C13—C14—C15108.6 (2)
N1—C2—H2107.6C13—C14—H14A110.0
C3—C2—H2107.6C15—C14—H14A110.0
C1—C2—H2107.6C13—C14—H14B110.0
C4—C3—C2112.6 (2)C15—C14—H14B110.0
C4—C3—H3A109.1H14A—C14—H14B108.3
C2—C3—H3A109.1N16—C15—C14109.4 (2)
C4—C3—H3B109.1N16—C15—H15A109.8
C2—C3—H3B109.1C14—C15—H15A109.8
H3A—C3—H3B107.8N16—C15—H15B109.8
C5—C4—C3114.0 (3)C14—C15—H15B109.8
C5—C4—H4A108.8H15A—C15—H15B108.2
C3—C4—H4A108.8C17—N16—C15125.8 (3)
C5—C4—H4B108.8C17—N16—H16111 (2)
C3—C4—H4B108.8C15—N16—H16123 (2)
H4A—C4—H4B107.6N16—C17—N18123.2 (3)
N6—C5—C4111.7 (2)N16—C17—N19117.9 (3)
N6—C5—H5A109.3N18—C17—N19118.9 (3)
C4—C5—H5A109.3C17—N18—H18A124 (2)
N6—C5—H5B109.3C17—N18—H18B114 (2)
C4—C5—H5B109.3H18A—N18—H18B121 (3)
H5A—C5—H5B107.9C17—N19—H19A117 (2)
C7—N6—C5123.2 (2)C17—N19—H19B114 (3)
C7—N6—H6121 (2)H19A—N19—H19B128 (4)
C5—N6—H6115 (2)O22—C23—O21125.7 (2)
N6—C7—N8121.7 (3)O22—C23—C24117.6 (2)
N6—C7—N9119.8 (2)O21—C23—C24116.6 (2)
N8—C7—N9118.6 (3)O25—C24—C26109.5 (2)
C7—N8—H8A122 (2)O25—C24—C23112.3 (2)
C7—N8—H8B118 (2)C26—C24—C23109.6 (2)
H8A—N8—H8B120 (3)O25—C24—H24108.4
C7—N9—H9A120 (2)C26—C24—H24108.4
C7—N9—H9B115 (2)C23—C24—H24108.4
H9A—N9—H9B125 (4)C24—O25—H25108 (3)
C12—N11—H11A108 (3)O27—C26—C24110.6 (2)
C12—N11—H11B116 (2)O27—C26—C28112.5 (2)
H11A—N11—H11B112 (3)C24—C26—C28109.9 (2)
C12—N11—H11C109 (2)O27—C26—H26107.9
H11A—N11—H11C112 (4)C24—C26—H26107.9
H11B—N11—H11C99 (3)C28—C26—H26107.9
O12—C11—O11126.5 (3)C26—O27—H27114 (3)
O12—C11—C12117.3 (3)O30—C28—O29125.9 (2)
O11—C11—C12116.1 (3)O30—C28—C26116.9 (2)
N11—C12—C11109.3 (2)O29—C28—C26117.1 (2)
O2—C1—C2—N1167.9 (2)C12—C13—C14—C15178.7 (3)
O1—C1—C2—N113.4 (3)C13—C14—C15—N16177.7 (3)
O2—C1—C2—C343.4 (3)C14—C15—N16—C17127.5 (4)
O1—C1—C2—C3137.9 (3)C15—N16—C17—N187.7 (5)
N1—C2—C3—C459.8 (3)C15—N16—C17—N19171.0 (3)
C1—C2—C3—C464.4 (3)O22—C23—C24—O25173.4 (2)
C2—C3—C4—C5159.6 (2)O21—C23—C24—O257.0 (3)
C3—C4—C5—N668.1 (4)O22—C23—C24—C2651.4 (3)
C4—C5—N6—C7170.5 (3)O21—C23—C24—C26129.0 (3)
C5—N6—C7—N84.8 (5)O25—C24—C26—O2772.9 (3)
C5—N6—C7—N9175.8 (3)C23—C24—C26—O2750.7 (3)
O12—C11—C12—N11151.9 (3)O25—C24—C26—C2851.9 (3)
O11—C11—C12—N1131.8 (3)C23—C24—C26—C28175.5 (2)
O12—C11—C12—C1389.4 (3)O27—C26—C28—O30175.7 (2)
O11—C11—C12—C1386.8 (3)C24—C26—C28—O3060.6 (3)
N11—C12—C13—C1459.8 (4)O27—C26—C28—O293.2 (3)
C11—C12—C13—C14177.9 (3)C24—C26—C28—O29120.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O210.89 (4)2.01 (4)2.892 (3)171 (3)
N1—H1B···O110.94 (3)1.82 (4)2.759 (3)177 (3)
N1—H1C···O22i0.91 (3)1.86 (3)2.770 (3)176 (3)
N6—H6···O27i0.90 (3)1.91 (3)2.785 (3)164 (3)
N8—H8A···O12ii0.82 (4)2.16 (4)2.961 (4)167 (4)
N8—H8B···O21iii0.84 (3)2.15 (3)2.934 (3)155 (3)
N9—H9A···O29i0.86 (4)2.30 (4)3.130 (4)162 (3)
N9—H9B···O21iii0.88 (4)2.33 (4)3.127 (4)151 (3)
N11—H11A···O10.84 (4)2.22 (4)3.046 (3)166 (4)
N11—H11B···O30iv0.93 (3)1.81 (3)2.732 (3)170 (3)
N11—H11C···O290.92 (5)1.99 (5)2.906 (4)176 (3)
N16—H16···O2v0.89 (3)1.92 (3)2.781 (3)162 (3)
N18—H18A···O1vi0.89 (3)2.00 (4)2.863 (3)165 (3)
N18—H18B···O29vii0.99 (4)1.86 (4)2.840 (3)168 (3)
N19—H19A···O2v0.90 (4)2.03 (4)2.841 (4)149 (3)
N19—H19B···O29vii0.90 (5)2.52 (5)3.224 (4)136 (4)
O25—H25···O10.832.232.840 (3)131
O27—H27···O110.86 (5)1.89 (5)2.698 (4)155 (4)
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x1, y, z; (iii) x, y+1/2, z+1; (iv) x+2, y+1/2, z+2; (v) x+2, y1/2, z+2; (vi) x+1, y, z; (vii) x+3, y+1/2, z+2.
(III) DL-lysine DL-tartaric acid monohydrate complex top
Crystal data top
2(C6H15N4O2)+·C4H4O62·H2OF(000) = 992
Mr = 460.49Dx = 1.400 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 732 reflections
a = 10.087 (3) Åθ = 2.2–21.5°
b = 23.003 (8) ŵ = 0.12 mm1
c = 9.414 (3) ÅT = 298 K
β = 90.820 (7)°Needle, colourless
V = 2184.2 (13) Å30.47 × 0.10 × 0.07 mm
Z = 4
Data collection top
Bruker SMART CCD area detector
diffractometer
2876 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
ϕ and ω scanh = 1111
15605 measured reflectionsk = 2727
3842 independent reflectionsl = 1111
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)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.218H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.1191P)2 + 1.8406P]
where P = (Fo2 + 2Fc2)/3
3842 reflections(Δ/σ)max < 0.001
379 parametersΔρmax = 0.75 e Å3
72 restraintsΔρmin = 0.30 e Å3
Crystal data top
2(C6H15N4O2)+·C4H4O62·H2OV = 2184.2 (13) Å3
Mr = 460.49Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.087 (3) ŵ = 0.12 mm1
b = 23.003 (8) ÅT = 298 K
c = 9.414 (3) Å0.47 × 0.10 × 0.07 mm
β = 90.820 (7)°
Data collection top
Bruker SMART CCD area detector
diffractometer
2876 reflections with I > 2σ(I)
15605 measured reflectionsRint = 0.046
3842 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07172 restraints
wR(F2) = 0.218H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.75 e Å3
3842 reflectionsΔρmin = 0.30 e Å3
379 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*/UeqOcc. (<1)
O10.0134 (3)0.27407 (11)0.4861 (3)0.0379 (7)
O20.0506 (3)0.21428 (11)0.3055 (3)0.0354 (7)
N10.0413 (3)0.18627 (14)0.6650 (3)0.0292 (7)
C10.0305 (3)0.22528 (15)0.4347 (4)0.0249 (8)
C20.0281 (4)0.17145 (15)0.5310 (4)0.0266 (8)
H20.02300.14100.48210.032*
C30.1655 (4)0.14802 (16)0.5622 (4)0.0298 (8)
H3A0.20430.13560.47360.036*
H3B0.15770.11400.62240.036*
C40.2591 (4)0.19074 (19)0.6339 (5)0.0434 (11)
H4A0.21470.20840.71390.052*
H4B0.28020.22140.56730.052*
C50.3889 (4)0.1624 (2)0.6870 (4)0.0403 (10)
H5A0.43590.18980.74770.048*
H5B0.36740.12870.74420.048*
C60.4792 (4)0.14372 (19)0.5696 (4)0.0384 (10)
H6A0.43740.11270.51530.046*
H6B0.49390.17620.50600.046*
N70.6089 (3)0.12301 (17)0.6284 (4)0.0361 (8)
O110.7280 (3)0.27196 (11)0.0007 (3)0.0388 (7)
O120.6893 (3)0.21413 (12)0.1837 (3)0.0394 (7)
N110.7798 (4)0.18248 (15)0.1768 (3)0.0275 (7)
C110.7100 (3)0.22335 (16)0.0534 (4)0.0271 (8)
C120.7115 (4)0.16932 (17)0.0403 (4)0.0334 (9)
H120.76770.14100.00810.040*
C13A0.5804 (4)0.1386 (2)0.0653 (5)0.0310 (12)0.764 (7)
H13A0.59500.10480.12530.037*0.764 (7)
H13B0.54300.12550.02460.037*0.764 (7)
C14A0.4837 (4)0.1803 (2)0.1371 (6)0.0396 (13)0.764 (7)
H14A0.46360.21200.07240.047*0.764 (7)
H14B0.52660.19670.22080.047*0.764 (7)
C15A0.3529 (5)0.1512 (3)0.1813 (5)0.0366 (14)0.764 (7)
H15A0.37400.11700.23740.044*0.764 (7)
H15B0.30530.17800.24180.044*0.764 (7)
C13B0.5638 (7)0.1712 (7)0.076 (2)0.041 (3)0.236 (7)
H13C0.51560.17470.01390.049*0.236 (7)
H13D0.54890.20690.12760.049*0.236 (7)
C14B0.4973 (13)0.1222 (7)0.1595 (17)0.036 (2)0.236 (7)
H14C0.54400.11890.25000.044*0.236 (7)
H14D0.51260.08620.10850.044*0.236 (7)
C15B0.3483 (12)0.1252 (10)0.1912 (10)0.033 (4)0.236 (7)
H15C0.32240.08970.23890.040*0.236 (7)
H15D0.33280.15730.25560.040*0.236 (7)
C160.2610 (4)0.13317 (19)0.0588 (4)0.0384 (10)
H16A0.25770.16420.01100.046*
H16B0.29730.09900.01320.046*
N170.1247 (3)0.12019 (16)0.1053 (4)0.0280 (7)
O210.7543 (3)0.09446 (11)0.3905 (3)0.0373 (7)
O220.7501 (3)0.00534 (12)0.4799 (3)0.0377 (7)
C230.7810 (3)0.04184 (16)0.3854 (4)0.0259 (8)
C240.8552 (3)0.01767 (14)0.2566 (4)0.0241 (8)
H240.80500.01530.21780.029*
O250.8629 (3)0.06098 (11)0.1511 (3)0.0297 (6)
C260.9936 (3)0.00365 (14)0.3015 (3)0.0222 (7)
H260.98480.03080.38110.027*
O271.0669 (3)0.04550 (10)0.3483 (2)0.0285 (6)
H271.12930.03480.39870.034*
C281.0578 (4)0.03539 (15)0.1778 (4)0.0250 (8)
O291.1434 (3)0.00923 (11)0.1073 (3)0.0353 (7)
O301.0169 (3)0.08603 (11)0.1534 (3)0.0377 (7)
O1W0.5810 (10)0.0235 (4)0.8233 (12)0.044 (3)0.33
O2W0.5197 (7)0.0006 (4)0.6244 (9)0.043 (2)0.34
O3W0.5695 (10)0.0083 (5)0.9114 (15)0.064 (3)0.33
H1A0.042 (5)0.154 (2)0.735 (5)0.057 (13)*
H1B0.137 (5)0.194 (2)0.635 (5)0.062 (15)*
H1C0.010 (5)0.221 (2)0.715 (5)0.054 (13)*
H7A0.647 (5)0.151 (2)0.693 (5)0.064 (15)*
H7B0.670 (5)0.111 (2)0.549 (6)0.069 (16)*
H7C0.593 (4)0.0920 (18)0.684 (4)0.028 (11)*
H11A0.862 (5)0.1893 (16)0.153 (4)0.031 (11)*
H11B0.788 (5)0.151 (2)0.222 (6)0.063 (16)*
H11C0.749 (5)0.213 (2)0.225 (5)0.042 (12)*
H17A0.130 (5)0.087 (2)0.146 (5)0.057 (15)*
H17B0.069 (5)0.106 (2)0.026 (6)0.065 (15)*
H17C0.102 (4)0.144 (2)0.158 (5)0.035 (13)*
H250.877 (5)0.043 (2)0.071 (6)0.070 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0555 (18)0.0255 (15)0.0327 (15)0.0007 (12)0.0053 (13)0.0008 (11)
O20.0471 (17)0.0356 (15)0.0237 (14)0.0048 (12)0.0051 (11)0.0014 (11)
N10.0334 (19)0.0283 (17)0.0260 (17)0.0004 (14)0.0043 (13)0.0036 (14)
C10.0247 (18)0.0265 (19)0.0233 (18)0.0009 (15)0.0030 (14)0.0004 (15)
C20.0282 (19)0.0277 (19)0.0240 (18)0.0021 (15)0.0009 (14)0.0001 (15)
C30.030 (2)0.029 (2)0.030 (2)0.0037 (16)0.0012 (16)0.0000 (15)
C40.036 (2)0.040 (2)0.055 (3)0.0038 (19)0.006 (2)0.009 (2)
C50.029 (2)0.054 (3)0.037 (2)0.0042 (19)0.0030 (17)0.0097 (19)
C60.031 (2)0.051 (3)0.032 (2)0.0005 (18)0.0031 (17)0.0059 (18)
N70.0295 (19)0.040 (2)0.038 (2)0.0032 (15)0.0045 (16)0.0058 (18)
O110.0478 (17)0.0312 (15)0.0375 (16)0.0026 (12)0.0004 (13)0.0006 (12)
O120.0528 (18)0.0418 (16)0.0236 (15)0.0088 (13)0.0070 (12)0.0064 (12)
N110.0286 (19)0.0261 (18)0.0277 (17)0.0011 (15)0.0020 (14)0.0024 (15)
C110.0212 (18)0.031 (2)0.029 (2)0.0014 (15)0.0005 (14)0.0030 (16)
C120.039 (2)0.037 (2)0.0243 (19)0.0091 (17)0.0016 (16)0.0019 (16)
C13A0.036 (3)0.021 (3)0.036 (3)0.007 (2)0.003 (2)0.001 (2)
C14A0.035 (3)0.036 (3)0.048 (3)0.005 (2)0.004 (2)0.009 (2)
C15A0.031 (3)0.041 (4)0.039 (3)0.006 (3)0.005 (2)0.006 (3)
C13B0.041 (6)0.041 (6)0.041 (5)0.016 (6)0.001 (5)0.004 (6)
C14B0.032 (4)0.037 (5)0.040 (5)0.006 (4)0.003 (4)0.001 (4)
C15B0.025 (6)0.041 (8)0.034 (6)0.008 (6)0.006 (5)0.003 (6)
C160.033 (2)0.050 (2)0.032 (2)0.0003 (18)0.0088 (17)0.0022 (18)
N170.0280 (18)0.0235 (18)0.0326 (19)0.0012 (14)0.0012 (15)0.0008 (16)
O210.0492 (17)0.0300 (15)0.0331 (15)0.0115 (12)0.0129 (12)0.0011 (11)
O220.0365 (16)0.0429 (16)0.0339 (15)0.0074 (12)0.0103 (12)0.0153 (12)
C230.0220 (18)0.029 (2)0.0264 (19)0.0027 (15)0.0016 (14)0.0030 (15)
C240.0301 (19)0.0196 (17)0.0228 (18)0.0002 (14)0.0008 (14)0.0001 (14)
O250.0445 (16)0.0259 (14)0.0189 (13)0.0085 (11)0.0026 (11)0.0030 (10)
C260.0293 (19)0.0176 (17)0.0199 (16)0.0016 (14)0.0024 (14)0.0015 (13)
O270.0340 (15)0.0258 (13)0.0256 (13)0.0021 (10)0.0052 (11)0.0020 (10)
C280.033 (2)0.0216 (18)0.0208 (17)0.0047 (15)0.0003 (14)0.0037 (14)
O290.0407 (16)0.0359 (15)0.0298 (15)0.0046 (12)0.0127 (12)0.0033 (11)
O300.065 (2)0.0197 (14)0.0281 (14)0.0012 (12)0.0071 (13)0.0030 (11)
O1W0.031 (5)0.045 (6)0.058 (6)0.008 (4)0.008 (5)0.037 (5)
O2W0.022 (4)0.055 (5)0.052 (5)0.007 (4)0.016 (4)0.014 (4)
O3W0.026 (5)0.063 (8)0.102 (10)0.009 (5)0.017 (6)0.045 (7)
Geometric parameters (Å, º) top
O1—C11.235 (4)C13A—H13B0.9700
O2—C11.261 (4)C14A—C15A1.542 (5)
N1—C21.491 (4)C14A—H14A0.9700
N1—H1A0.99 (5)C14A—H14B0.9700
N1—H1B1.02 (5)C15A—C161.527 (5)
N1—H1C1.06 (5)C15A—H15A0.9700
C1—C21.535 (5)C15A—H15B0.9700
C2—C31.512 (5)C13B—C14B1.536 (6)
C2—H20.9800C13B—H13C0.9700
C3—C41.515 (5)C13B—H13D0.9700
C3—H3A0.9700C14B—C15B1.538 (6)
C3—H3B0.9700C14B—H14C0.9700
C4—C51.540 (6)C14B—H14D0.9700
C4—H4A0.9700C15B—C161.527 (6)
C4—H4B0.9700C15B—H15C0.9700
C5—C61.504 (5)C15B—H15D0.9700
C5—H5A0.9700C16—N171.479 (5)
C5—H5B0.9700C16—H16A0.9700
C6—N71.492 (5)C16—H16B0.9700
C6—H6A0.9700N17—H17A0.85 (6)
C6—H6B0.9700N17—H17B0.98 (6)
N7—H7A0.96 (6)N17—H17C0.78 (5)
N7—H7B1.02 (6)O21—C231.241 (4)
N7—H7C0.90 (4)O22—C231.265 (4)
O11—C111.241 (4)C23—C241.539 (5)
O12—C111.259 (4)C24—O251.409 (4)
N11—C121.481 (5)C24—C261.534 (5)
N11—H11A0.87 (5)C24—H240.9800
N11—H11B0.84 (5)O25—H250.88 (6)
N11—H11C0.90 (5)C26—O271.418 (4)
C11—C121.524 (5)C26—C281.526 (5)
C12—C13A1.520 (5)C26—H260.9800
C12—C13B1.531 (6)O27—H270.8200
C12—H120.9800C28—O291.252 (4)
C13A—C14A1.532 (5)C28—O301.256 (4)
C13A—H13A0.9700
C2—N1—H1A114 (3)C14A—C13A—H13B109.7
C2—N1—H1B105 (3)H13A—C13A—H13B108.2
H1A—N1—H1B108 (4)C13A—C14A—C15A113.6 (4)
C2—N1—H1C109 (3)C13A—C14A—H14A108.8
H1A—N1—H1C106 (4)C15A—C14A—H14A108.8
H1B—N1—H1C116 (4)C13A—C14A—H14B108.8
O1—C1—O2125.8 (3)C15A—C14A—H14B108.8
O1—C1—C2119.9 (3)H14A—C14A—H14B107.7
O2—C1—C2114.3 (3)C16—C15A—C14A115.3 (4)
N1—C2—C3110.9 (3)C16—C15A—H15A108.4
N1—C2—C1109.1 (3)C14A—C15A—H15A108.4
C3—C2—C1112.3 (3)C16—C15A—H15B108.4
N1—C2—H2108.1C14A—C15A—H15B108.4
C3—C2—H2108.1H15A—C15A—H15B107.5
C1—C2—H2108.1C12—C13B—C14B121.7 (10)
C2—C3—C4114.8 (3)C12—C13B—H13C106.9
C2—C3—H3A108.6C14B—C13B—H13C106.9
C4—C3—H3A108.6C12—C13B—H13D106.9
C2—C3—H3B108.6C14B—C13B—H13D106.9
C4—C3—H3B108.6H13C—C13B—H13D106.7
H3A—C3—H3B107.5C13B—C14B—C15B120.1 (12)
C3—C4—C5113.0 (3)C13B—C14B—H14C107.3
C3—C4—H4A109.0C15B—C14B—H14C107.3
C5—C4—H4A109.0C13B—C14B—H14D107.3
C3—C4—H4B109.0C15B—C14B—H14D107.3
C5—C4—H4B109.0H14C—C14B—H14D106.9
H4A—C4—H4B107.8C16—C15B—C14B113.7 (10)
C6—C5—C4113.8 (3)C16—C15B—H15C108.8
C6—C5—H5A108.8C14B—C15B—H15C108.8
C4—C5—H5A108.8C16—C15B—H15D108.8
C6—C5—H5B108.8C14B—C15B—H15D108.8
C4—C5—H5B108.8H15C—C15B—H15D107.7
H5A—C5—H5B107.7N17—C16—C15A112.8 (3)
N7—C6—C5110.8 (3)N17—C16—C15B105.2 (6)
N7—C6—H6A109.5N17—C16—H16A109.0
C5—C6—H6A109.5C15A—C16—H16A109.0
N7—C6—H6B109.5C15B—C16—H16A130.9
C5—C6—H6B109.5N17—C16—H16B109.0
H6A—C6—H6B108.1C15A—C16—H16B109.0
C6—N7—H7A111 (3)C15B—C16—H16B92.7
C6—N7—H7B111 (3)H16A—C16—H16B107.8
H7A—N7—H7B114 (4)C16—N17—H17A105 (3)
C6—N7—H7C108 (3)C16—N17—H17B111 (3)
H7A—N7—H7C104 (4)H17A—N17—H17B95 (4)
H7B—N7—H7C108 (4)C16—N17—H17C109 (3)
C12—N11—H11A104 (3)H17A—N17—H17C111 (5)
C12—N11—H11B108 (4)H17B—N17—H17C123 (4)
H11A—N11—H11B102 (4)O21—C23—O22124.4 (3)
C12—N11—H11C116 (3)O21—C23—C24119.4 (3)
H11A—N11—H11C109 (4)O22—C23—C24116.2 (3)
H11B—N11—H11C116 (5)O25—C24—C26111.2 (3)
O11—C11—O12125.0 (3)O25—C24—C23109.4 (3)
O11—C11—C12119.8 (3)C26—C24—C23110.5 (3)
O12—C11—C12115.3 (3)O25—C24—H24108.6
N11—C12—C13A110.8 (3)C26—C24—H24108.6
N11—C12—C11109.7 (3)C23—C24—H24108.6
C13A—C12—C11117.9 (3)C24—O25—H25106 (4)
N11—C12—C13B104.4 (8)O27—C26—C28113.2 (3)
C11—C12—C13B95.8 (6)O27—C26—C24107.4 (3)
N11—C12—H12105.9C28—C26—C24109.7 (3)
C13A—C12—H12105.9O27—C26—H26108.8
C11—C12—H12105.9C28—C26—H26108.8
C13B—C12—H12133.7C24—C26—H26108.8
C12—C13A—C14A109.7 (4)C26—O27—H27109.5
C12—C13A—H13A109.7O29—C28—O30125.2 (3)
C14A—C13A—H13A109.7O29—C28—C26118.6 (3)
C12—C13A—H13B109.7O30—C28—C26116.2 (3)
O1—C1—C2—N119.6 (5)N11—C12—C13B—C14B74.1 (17)
O2—C1—C2—N1160.3 (3)C11—C12—C13B—C14B173.8 (16)
O1—C1—C2—C3103.8 (4)C12—C13B—C14B—C15B179.2 (14)
O2—C1—C2—C376.3 (4)C13B—C14B—C15B—C1655 (2)
N1—C2—C3—C463.5 (4)C14A—C15A—C16—N17164.9 (4)
C1—C2—C3—C458.9 (4)C14B—C15B—C16—N17166.1 (13)
C2—C3—C4—C5170.0 (3)O21—C23—C24—O259.1 (4)
C3—C4—C5—C669.8 (5)O22—C23—C24—O25170.3 (3)
C4—C5—C6—N7173.5 (4)O21—C23—C24—C26113.6 (4)
O11—C11—C12—N1119.3 (5)O22—C23—C24—C2667.0 (4)
O12—C11—C12—N11160.9 (3)O25—C24—C26—O2756.8 (3)
O11—C11—C12—C13A108.7 (4)C23—C24—C26—O2764.8 (3)
O12—C11—C12—C13A71.1 (5)O25—C24—C26—C2866.6 (3)
O11—C11—C12—C13B88.2 (9)C23—C24—C26—C28171.8 (3)
O12—C11—C12—C13B91.6 (9)O27—C26—C28—O2918.0 (4)
N11—C12—C13A—C14A67.3 (5)C24—C26—C28—O29102.0 (4)
C11—C12—C13A—C14A60.1 (5)O27—C26—C28—O30163.6 (3)
C12—C13A—C14A—C15A173.9 (4)C24—C26—C28—O3076.5 (4)
C13A—C14A—C15A—C1669.4 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30i0.99 (5)1.90 (5)2.879 (4)168 (4)
N1—H1B···O11ii1.02 (5)2.00 (5)2.938 (5)151 (4)
N1—H1C···O2iii1.06 (5)1.75 (5)2.794 (4)165 (4)
N7—H7A···O12iv0.96 (6)1.90 (6)2.852 (5)169 (5)
N7—H7B···O211.02 (6)1.77 (6)2.774 (4)169 (5)
N7—H7C···O1W0.90 (4)2.06 (4)2.950 (9)172 (4)
N7—H7C···O2W0.90 (4)2.30 (4)2.956 (9)130 (3)
N11—H11A···O1v0.87 (5)2.36 (5)3.146 (5)149 (3)
N11—H11A···O2vi0.87 (5)2.44 (4)3.061 (4)129 (3)
N11—H11B···O210.84 (5)2.09 (6)2.868 (4)155 (5)
N11—H11B···O250.84 (5)2.31 (5)2.929 (4)131 (4)
N11—H11C···O12iii0.90 (5)1.98 (5)2.872 (5)174 (4)
N17—H17A···O27vii0.85 (6)2.24 (5)2.926 (4)138 (4)
N17—H17A···O29vii0.85 (6)2.25 (6)2.983 (5)144 (4)
N17—H17B···O30viii0.98 (6)1.94 (6)2.915 (5)169 (4)
N17—H17C···O20.78 (5)2.20 (5)2.972 (5)176 (4)
O25—H25···O29ix0.88 (6)1.85 (6)2.708 (4)164 (5)
O27—H27···O22x0.821.902.702 (4)167
O3W—O29···2.904 (1)xi3_756O3WO1W3 (1)
Symmetry codes: (i) x+1, y, z+1; (ii) x1, y+1/2, z+1/2; (iii) x, y+1/2, z+1/2; (iv) x, y, z+1; (v) x+1, y+1/2, z1/2; (vi) x+1, y, z; (vii) x1, y, z; (viii) x+1, y, z; (ix) x+2, y, z; (x) x+2, y, z+1; (xi) x+1, y, z+2.
(IV) L-lysine D-hydrogen tartrate top
Crystal data top
C6H15N2O2+·C4H5O6F(000) = 316
Mr = 296.28Dx = 1.494 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1435 reflections
a = 5.1849 (11) Åθ = 2.4–21.5°
b = 16.667 (4) ŵ = 0.13 mm1
c = 7.6701 (17) ÅT = 2983 K
β = 96.366 (4)°Plate, colourless
V = 658.7 (2) Å30.4 × 0.35 × 0.2 mm
Z = 2
Data collection top
Bruker SMART CCD area detector
diffractometer
1231 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 26.0°, θmin = 2.4°
ϕ and ω scanh = 66
4251 measured reflectionsk = 2017
1342 independent reflectionsl = 99
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.0479P)2 + 0.0738P]
where P = (Fo2 + 2Fc2)/3
1342 reflections(Δ/σ)max < 0.001
242 parametersΔρmax = 0.15 e Å3
79 restraintsΔρmin = 0.16 e Å3
Crystal data top
C6H15N2O2+·C4H5O6V = 658.7 (2) Å3
Mr = 296.28Z = 2
Monoclinic, P21Mo Kα radiation
a = 5.1849 (11) ŵ = 0.13 mm1
b = 16.667 (4) ÅT = 2983 K
c = 7.6701 (17) Å0.4 × 0.35 × 0.2 mm
β = 96.366 (4)°
Data collection top
Bruker SMART CCD area detector
diffractometer
1231 reflections with I > 2σ(I)
4251 measured reflectionsRint = 0.025
1342 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04079 restraints
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.15 e Å3
1342 reflectionsΔρmin = 0.16 e Å3
242 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*/UeqOcc. (<1)
N70.3338 (7)0.3679 (2)0.8340 (4)0.0379 (7)
C30.1426 (6)0.5083 (2)0.3292 (4)0.0344 (8)
H3A0.20580.54130.41950.041*
H3B0.26730.46550.30140.041*
C40.1164 (6)0.4714 (2)0.4015 (4)0.0335 (7)
H4A0.16810.43200.31910.040*
H4B0.24810.51290.41470.040*
C50.0981 (6)0.4319 (2)0.5762 (4)0.0332 (7)
H5A0.03440.39050.56220.040*
H5B0.04480.47150.65770.040*
C60.3511 (6)0.3947 (2)0.6526 (4)0.0378 (8)
H6A0.39170.34940.58130.045*
H6B0.48970.43380.65140.045*
N10.3834 (6)0.5972 (2)0.1137 (4)0.0347 (7)
C1A0.0476 (7)0.5043 (3)0.0209 (6)0.0367 (14)0.815 (11)
O1A0.2208 (7)0.4677 (4)0.0683 (6)0.0633 (18)0.815 (11)
O2A0.1872 (8)0.4939 (4)0.0151 (7)0.0462 (16)0.815 (11)
C20.1273 (6)0.5593 (2)0.1655 (4)0.0290 (7)
H20.00420.60120.19090.035*
C1B0.050 (2)0.525 (2)0.0078 (17)0.045 (4)0.185 (11)
O1B0.219 (3)0.5240 (17)0.1343 (15)0.057 (5)0.185 (11)
O2B0.185 (2)0.5208 (17)0.019 (2)0.041 (5)0.185 (11)
O110.7396 (4)0.25423 (15)0.0671 (3)0.0367 (6)
O121.1371 (4)0.23138 (18)0.0588 (3)0.0436 (7)
C130.9078 (6)0.24863 (18)0.0650 (3)0.0245 (6)
C140.8172 (6)0.26391 (19)0.2467 (4)0.0263 (7)
H140.94710.29840.31200.032*
O150.5765 (5)0.30320 (16)0.2419 (3)0.0358 (6)
C160.8172 (7)0.1839 (2)0.3447 (4)0.0310 (7)
H160.99240.16100.35600.037*
O170.6431 (5)0.13050 (16)0.2485 (3)0.0478 (7)
H170.72520.09430.20780.057*
C180.7312 (6)0.1959 (2)0.5264 (4)0.0294 (7)
O190.5315 (5)0.16599 (17)0.5662 (3)0.0476 (7)
O200.8893 (4)0.23808 (15)0.6323 (3)0.0367 (6)
H1A0.371 (7)0.629 (3)0.023 (5)0.048 (11)*
H1B0.446 (8)0.623 (3)0.206 (6)0.048 (11)*
H1C0.497 (9)0.561 (3)0.084 (5)0.052 (13)*
H7A0.276 (7)0.413 (3)0.909 (5)0.049 (11)*
H7B0.464 (8)0.345 (3)0.886 (5)0.045 (11)*
H7C0.207 (10)0.331 (3)0.846 (6)0.067 (14)*
H150.453 (9)0.277 (3)0.182 (6)0.064 (15)*
H200.836 (9)0.239 (3)0.749 (6)0.077 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N70.0319 (16)0.0392 (19)0.0424 (16)0.0078 (16)0.0029 (13)0.0062 (15)
C30.0330 (17)0.0359 (19)0.0359 (18)0.0052 (15)0.0113 (14)0.0048 (14)
C40.0312 (16)0.038 (2)0.0321 (15)0.0014 (15)0.0071 (12)0.0001 (15)
C50.0272 (16)0.035 (2)0.0375 (17)0.0035 (14)0.0060 (13)0.0028 (14)
C60.0317 (18)0.048 (2)0.0344 (19)0.0053 (16)0.0066 (14)0.0003 (15)
N10.0424 (18)0.0363 (18)0.0265 (14)0.0061 (15)0.0086 (13)0.0006 (14)
C1A0.033 (2)0.048 (3)0.032 (2)0.006 (2)0.0141 (18)0.006 (2)
O1A0.038 (2)0.084 (4)0.070 (3)0.018 (2)0.0154 (18)0.045 (3)
O2A0.034 (2)0.064 (4)0.043 (2)0.0026 (18)0.0142 (16)0.017 (2)
C20.0297 (17)0.0290 (18)0.0290 (16)0.0002 (14)0.0063 (13)0.0025 (13)
C1B0.032 (7)0.062 (8)0.041 (7)0.003 (6)0.008 (6)0.021 (7)
O1B0.037 (7)0.085 (11)0.049 (8)0.006 (8)0.002 (6)0.034 (7)
O2B0.025 (7)0.066 (11)0.035 (8)0.013 (7)0.014 (6)0.003 (8)
O110.0372 (13)0.0517 (16)0.0208 (10)0.0112 (11)0.0018 (9)0.0040 (10)
O120.0262 (12)0.0686 (19)0.0368 (13)0.0042 (13)0.0064 (9)0.0096 (12)
C130.0265 (15)0.0255 (17)0.0221 (14)0.0032 (13)0.0057 (12)0.0001 (12)
C140.0255 (15)0.0301 (18)0.0228 (14)0.0005 (13)0.0005 (12)0.0035 (12)
O150.0407 (14)0.0349 (13)0.0329 (12)0.0100 (11)0.0096 (10)0.0047 (10)
C160.0390 (18)0.0307 (19)0.0232 (14)0.0034 (14)0.0023 (13)0.0010 (13)
O170.0730 (19)0.0342 (14)0.0352 (14)0.0064 (13)0.0012 (12)0.0073 (11)
C180.0349 (17)0.0302 (17)0.0234 (14)0.0011 (14)0.0041 (13)0.0051 (13)
O190.0506 (15)0.0603 (17)0.0333 (13)0.0233 (13)0.0117 (11)0.0021 (12)
O200.0426 (13)0.0478 (16)0.0199 (10)0.0120 (12)0.0043 (9)0.0027 (10)
Geometric parameters (Å, º) top
N7—C61.474 (4)C1A—O2A1.235 (4)
N7—H7A1.01 (4)C1A—C21.531 (5)
N7—H7B0.84 (5)C2—C1B1.539 (9)
N7—H7C0.91 (6)C2—H20.9800
C3—C41.524 (5)C1B—O1B1.233 (5)
C3—C21.526 (4)C1B—O2B1.235 (5)
C3—H3A0.9700O11—C131.264 (4)
C3—H3B0.9700O12—C131.229 (4)
C4—C51.506 (4)C13—C141.541 (4)
C4—H4A0.9700C14—O151.406 (4)
C4—H4B0.9700C14—C161.531 (4)
C5—C61.509 (5)C14—H140.9800
C5—H5A0.9700O15—H150.87 (5)
C5—H5B0.9700C16—O171.416 (4)
C6—H6A0.9700C16—C181.523 (4)
C6—H6B0.9700C16—H160.9800
N1—C21.484 (4)O17—H170.8200
N1—H1A0.89 (4)C18—O191.218 (4)
N1—H1B0.91 (4)C18—O201.296 (4)
N1—H1C0.86 (5)O20—H200.96 (5)
C1A—O1A1.229 (4)
C6—N7—H7A111 (2)O1A—C1A—O2A124.9 (4)
C6—N7—H7B117 (3)O1A—C1A—C2117.5 (3)
H7A—N7—H7B110 (4)O2A—C1A—C2117.1 (3)
C6—N7—H7C115 (3)N1—C2—C3109.3 (2)
H7A—N7—H7C100 (4)N1—C2—C1A111.5 (3)
H7B—N7—H7C101 (4)C3—C2—C1A107.8 (3)
C4—C3—C2113.6 (2)N1—C2—C1B103.7 (7)
C4—C3—H3A108.8C3—C2—C1B123.1 (14)
C2—C3—H3A108.8N1—C2—H2109.4
C4—C3—H3B108.8C3—C2—H2109.4
C2—C3—H3B108.8C1A—C2—H2109.4
H3A—C3—H3B107.7C1B—C2—H2101.1
C5—C4—C3111.1 (2)O1B—C1B—O2B124.3 (10)
C5—C4—H4A109.4O1B—C1B—C2117.1 (8)
C3—C4—H4A109.4O2B—C1B—C2115.9 (8)
C5—C4—H4B109.4O12—C13—O11124.8 (3)
C3—C4—H4B109.4O12—C13—C14117.8 (3)
H4A—C4—H4B108.0O11—C13—C14117.4 (2)
C4—C5—C6112.8 (3)O15—C14—C16111.7 (2)
C4—C5—H5A109.0O15—C14—C13114.3 (2)
C6—C5—H5A109.0C16—C14—C13108.5 (2)
C4—C5—H5B109.0O15—C14—H14107.3
C6—C5—H5B109.0C16—C14—H14107.3
H5A—C5—H5B107.8C13—C14—H14107.3
N7—C6—C5110.5 (3)C14—O15—H15112 (3)
N7—C6—H6A109.6O17—C16—C18109.0 (3)
C5—C6—H6A109.6O17—C16—C14109.1 (2)
N7—C6—H6B109.6C18—C16—C14110.5 (3)
C5—C6—H6B109.6O17—C16—H16109.4
H6A—C6—H6B108.1C18—C16—H16109.4
C2—N1—H1A109 (2)C14—C16—H16109.4
C2—N1—H1B112 (3)C16—O17—H17109.5
H1A—N1—H1B113 (4)O19—C18—O20124.2 (3)
C2—N1—H1C110 (3)O19—C18—C16121.3 (3)
H1A—N1—H1C109 (4)O20—C18—C16114.6 (3)
H1B—N1—H1C104 (4)C18—O20—H20111 (3)
C2—C3—C4—C5171.8 (3)C3—C2—C1B—O2B85 (3)
C3—C4—C5—C6179.9 (3)O12—C13—C14—O15164.1 (3)
C4—C5—C6—N7171.4 (3)O11—C13—C14—O1516.4 (4)
C4—C3—C2—N1175.8 (3)O12—C13—C14—C1670.5 (4)
C4—C3—C2—C1A62.9 (4)O11—C13—C14—C16109.0 (3)
C4—C3—C2—C1B62.3 (8)O15—C14—C16—O1766.2 (3)
O1A—C1A—C2—N134.1 (6)C13—C14—C16—O1760.7 (3)
O2A—C1A—C2—N1153.2 (5)O15—C14—C16—C1853.6 (3)
O1A—C1A—C2—C385.8 (6)C13—C14—C16—C18179.5 (2)
O2A—C1A—C2—C386.8 (5)O17—C16—C18—O194.4 (4)
N1—C2—C1B—O1B11 (3)C14—C16—C18—O19115.4 (4)
C3—C2—C1B—O1B113 (2)O17—C16—C18—O20174.1 (3)
N1—C2—C1B—O2B151 (2)C14—C16—C18—O2066.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O12i0.89 (4)2.22 (4)2.959 (4)141 (3)
N1—H1A···O17ii0.89 (4)2.38 (4)3.001 (4)127 (3)
N1—H1B···O19iii0.91 (4)1.99 (4)2.890 (4)169 (4)
N1—H1C···O2Aiv0.86 (5)2.00 (5)2.849 (6)169 (4)
N7—H7A···O2Av1.01 (4)1.67 (5)2.675 (5)174 (4)
N7—H7B···O11v0.84 (5)2.08 (5)2.870 (4)156 (4)
N7—H7C···O12vi0.91 (6)2.38 (5)3.095 (4)135 (4)
O15—H15···O12iv0.87 (5)1.95 (5)2.808 (4)170 (5)
O17—H17···O2Avii0.822.473.230 (7)155
O20—H20···O11v0.96 (5)1.57 (5)2.528 (3)171 (5)
Symmetry codes: (i) x+1, y+1/2, z; (ii) x, y+1/2, z; (iii) x, y+1/2, z+1; (iv) x1, y, z; (v) x, y, z+1; (vi) x1, y, z+1; (vii) x+1, y1/2, z.
(V) L-lysine L-hydrogen tartrate top
Crystal data top
C6H15N2O2+·C4H5O6F(000) = 316
Mr = 296.28Dx = 1.478 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1401 reflections
a = 5.1022 (11) Åθ = 2.3–24.0°
b = 17.444 (4) ŵ = 0.13 mm1
c = 7.547 (2) ÅT = 298 K
β = 97.748 (4)°Plate, colourless
V = 665.6 (3) Å30.35 × 0.25 × 0.20 mm
Z = 2
Data collection top
Bruker SMART CCD area detector
diffractometer
1146 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 25.0°, θmin = 2.3°
ϕ and ω scanh = 56
3396 measured reflectionsk = 2020
1200 independent reflectionsl = 68
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) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.0484P)2 + 0.3283P]
where P = (Fo2 + 2Fc2)/3
1200 reflections(Δ/σ)max = 0.001
288 parametersΔρmax = 0.25 e Å3
303 restraintsΔρmin = 0.19 e Å3
Crystal data top
C6H15N2O2+·C4H5O6V = 665.6 (3) Å3
Mr = 296.28Z = 2
Monoclinic, P21Mo Kα radiation
a = 5.1022 (11) ŵ = 0.13 mm1
b = 17.444 (4) ÅT = 298 K
c = 7.547 (2) Å0.35 × 0.25 × 0.20 mm
β = 97.748 (4)°
Data collection top
Bruker SMART CCD area detector
diffractometer
1146 reflections with I > 2σ(I)
3396 measured reflectionsRint = 0.028
1200 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.048303 restraints
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.25 e Å3
1200 reflectionsΔρmin = 0.19 e Å3
288 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*/UeqOcc. (<1)
O1A0.060 (3)0.2889 (10)0.017 (2)0.058 (3)0.608 (6)
O2A0.185 (2)0.3939 (7)0.0531 (15)0.055 (3)0.608 (6)
N1A0.264 (3)0.2161 (5)0.1687 (15)0.044 (3)0.608 (6)
HA1A0.09150.20540.18190.066*0.608 (6)
HA1B0.34410.19210.07230.066*0.608 (6)
HA1C0.33190.20040.26480.066*0.608 (6)
N7A0.304 (4)0.4380 (10)0.8529 (13)0.055 (3)0.608 (6)
HA7A0.24750.48620.84140.083*0.608 (6)
HA7B0.46650.43710.91310.083*0.608 (6)
HA7C0.19570.41100.91200.083*0.608 (6)
C1A0.123 (2)0.3301 (6)0.0162 (13)0.043 (2)0.608 (6)
C2A0.3021 (16)0.2996 (4)0.1470 (11)0.0406 (19)0.608 (6)
H2A0.48580.30850.09440.049*0.608 (6)
C3A0.2569 (14)0.3413 (4)0.3220 (10)0.0481 (16)0.608 (6)
H3A10.35050.31410.40660.058*0.608 (6)
H3A20.33540.39180.30510.058*0.608 (6)
C4A0.0281 (16)0.3506 (7)0.4045 (12)0.057 (2)0.608 (6)
H4A10.11210.30080.42050.068*0.608 (6)
H4A20.12310.38080.32590.068*0.608 (6)
C5A0.0372 (17)0.3901 (6)0.5825 (12)0.0594 (18)0.608 (6)
H5A10.05420.43880.56480.071*0.608 (6)
H5A20.05740.35910.65960.071*0.608 (6)
C6A0.3080 (16)0.4041 (6)0.6737 (12)0.061 (2)0.608 (6)
H6A10.39950.43850.60180.073*0.608 (6)
H6A20.40450.35600.68550.073*0.608 (6)
O1B0.102 (4)0.2779 (13)0.020 (3)0.053 (4)0.392 (6)
O2B0.137 (4)0.3842 (9)0.004 (2)0.052 (3)0.392 (6)
N1B0.315 (5)0.2029 (8)0.152 (2)0.041 (3)0.392 (6)
HB1A0.17300.17940.12060.061*0.392 (6)
HB1B0.44730.19980.06260.061*0.392 (6)
HB1C0.36180.18030.24860.061*0.392 (6)
N7B0.312 (6)0.4550 (15)0.8378 (16)0.048 (4)0.392 (6)
HB7A0.16090.44370.87860.072*0.392 (6)
HB7B0.36850.50080.87870.072*0.392 (6)
HB7C0.43290.41970.87500.072*0.392 (6)
C1B0.093 (4)0.3156 (10)0.0480 (18)0.046 (3)0.392 (6)
C2B0.252 (3)0.2843 (8)0.1919 (16)0.044 (2)0.392 (6)
H2B0.41630.31350.18910.053*0.392 (6)
C3B0.089 (2)0.2925 (6)0.3744 (15)0.055 (2)0.392 (6)
H3B10.18910.27160.46380.066*0.392 (6)
H3B20.07110.26250.37680.066*0.392 (6)
C4B0.015 (3)0.3741 (7)0.424 (2)0.062 (3)0.392 (6)
H4B10.03170.40060.31940.074*0.392 (6)
H4B20.16650.40010.46140.074*0.392 (6)
C5B0.210 (3)0.3772 (7)0.569 (2)0.069 (2)0.392 (6)
H5B10.36610.35690.52550.083*0.392 (6)
H5B20.17120.34460.66670.083*0.392 (6)
C6B0.268 (3)0.4564 (7)0.6396 (17)0.060 (2)0.392 (6)
H6B10.42480.47600.59490.072*0.392 (6)
H6B20.12130.49000.59850.072*0.392 (6)
O110.3544 (5)0.0759 (2)1.1095 (3)0.0403 (7)
O120.0654 (5)0.0868 (2)0.9926 (3)0.0376 (6)
C130.1708 (7)0.0760 (2)0.9791 (4)0.0294 (8)
C140.2475 (7)0.0643 (2)0.7912 (5)0.0320 (9)
H140.11390.03090.72550.038*
O150.4948 (6)0.02965 (18)0.7877 (4)0.0363 (7)
H150.610 (9)0.057 (3)0.847 (6)0.035 (12)*
C160.2275 (8)0.1430 (3)0.6977 (5)0.0382 (10)
H160.04170.15900.67820.046*
O170.3761 (8)0.1986 (2)0.8029 (4)0.0540 (9)
H170.285 (14)0.232 (5)0.860 (10)0.10 (2)*
C180.3290 (9)0.1367 (3)0.5176 (5)0.0430 (11)
O190.5278 (9)0.1689 (3)0.4848 (5)0.0711 (12)
O200.1809 (6)0.0936 (3)0.4058 (4)0.0610 (11)
H200.250 (16)0.085 (6)0.304 (11)0.13 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.045 (6)0.053 (5)0.083 (7)0.017 (4)0.033 (6)0.005 (4)
O2A0.054 (5)0.045 (4)0.068 (6)0.009 (3)0.018 (4)0.020 (3)
N1A0.053 (7)0.036 (5)0.047 (4)0.015 (4)0.022 (4)0.014 (3)
N7A0.059 (5)0.045 (7)0.066 (5)0.028 (5)0.027 (5)0.026 (5)
C1A0.036 (4)0.027 (5)0.067 (4)0.003 (4)0.012 (4)0.005 (4)
C2A0.035 (4)0.028 (4)0.062 (4)0.004 (3)0.019 (3)0.003 (3)
C3A0.050 (3)0.037 (3)0.060 (4)0.002 (3)0.019 (3)0.018 (3)
C4A0.056 (4)0.051 (4)0.066 (4)0.000 (3)0.012 (3)0.016 (3)
C5A0.056 (4)0.054 (4)0.070 (4)0.004 (3)0.017 (3)0.018 (3)
C6A0.057 (4)0.057 (4)0.072 (4)0.016 (4)0.022 (3)0.023 (4)
O1B0.035 (7)0.050 (8)0.078 (9)0.004 (5)0.027 (7)0.000 (6)
O2B0.047 (7)0.034 (6)0.081 (9)0.004 (5)0.024 (7)0.005 (6)
N1B0.036 (7)0.034 (6)0.055 (7)0.021 (5)0.020 (5)0.011 (5)
N7B0.044 (7)0.042 (10)0.066 (6)0.012 (6)0.038 (5)0.010 (5)
C1B0.039 (5)0.030 (5)0.073 (5)0.005 (4)0.023 (4)0.004 (4)
C2B0.038 (4)0.033 (5)0.066 (5)0.002 (4)0.024 (4)0.009 (4)
C3B0.050 (4)0.044 (4)0.069 (4)0.001 (4)0.004 (4)0.020 (4)
C4B0.059 (4)0.048 (5)0.077 (4)0.005 (4)0.003 (4)0.020 (4)
C5B0.065 (5)0.059 (5)0.080 (5)0.001 (4)0.002 (4)0.025 (4)
C6B0.062 (5)0.047 (5)0.070 (5)0.000 (5)0.004 (4)0.018 (5)
O110.0308 (13)0.0699 (19)0.0204 (12)0.0069 (15)0.0037 (10)0.0024 (14)
O120.0247 (13)0.0583 (18)0.0311 (13)0.0024 (13)0.0085 (10)0.0027 (13)
C130.0296 (19)0.034 (2)0.0248 (18)0.0015 (16)0.0057 (14)0.0003 (17)
C140.0254 (18)0.047 (2)0.0236 (18)0.0006 (16)0.0042 (14)0.0098 (16)
O150.0333 (15)0.0463 (16)0.0310 (14)0.0035 (13)0.0101 (11)0.0085 (13)
C160.035 (2)0.058 (3)0.0229 (19)0.0136 (19)0.0084 (15)0.0042 (18)
O170.079 (2)0.0457 (19)0.0383 (17)0.0004 (18)0.0130 (16)0.0044 (14)
C180.040 (2)0.067 (3)0.0231 (19)0.011 (2)0.0074 (17)0.005 (2)
O190.078 (3)0.099 (3)0.043 (2)0.017 (2)0.0317 (18)0.0054 (18)
O200.0477 (18)0.112 (3)0.0252 (16)0.005 (2)0.0126 (14)0.0116 (18)
Geometric parameters (Å, º) top
O1A—C1A1.230 (8)N7B—HB7A0.8900
O2A—C1A1.252 (10)N7B—HB7B0.8900
N1A—C2A1.477 (10)N7B—HB7C0.8900
N1A—HA1A0.8900C1B—C2B1.540 (10)
N1A—HA1B0.8900C2B—C3B1.515 (12)
N1A—HA1C0.8900C2B—H2B0.9800
N7A—C6A1.479 (11)C3B—C4B1.505 (12)
N7A—HA7A0.8900C3B—H3B10.9700
N7A—HA7B0.8900C3B—H3B20.9700
N7A—HA7C0.8900C4B—C5B1.481 (12)
C1A—C2A1.529 (9)C4B—H4B10.9700
C2A—C3A1.497 (9)C4B—H4B20.9700
C2A—H2A0.9800C5B—C6B1.495 (12)
C3A—C4A1.511 (10)C5B—H5B10.9700
C3A—H3A10.9700C5B—H5B20.9700
C3A—H3A20.9700C6B—H6B10.9700
C4A—C5A1.505 (10)C6B—H6B20.9700
C4A—H4A10.9700O11—C131.264 (4)
C4A—H4A20.9700O12—C131.237 (4)
C5A—C6A1.478 (11)C13—C141.535 (5)
C5A—H5A10.9700C14—O151.402 (4)
C5A—H5A20.9700C14—C161.540 (6)
C6A—H6A10.9700C14—H140.9800
C6A—H6A20.9700O15—H150.84 (5)
O1B—C1B1.233 (10)C16—O171.408 (6)
O2B—C1B1.255 (11)C16—C181.522 (5)
N1B—C2B1.479 (10)C16—H160.9800
N1B—HB1A0.8900O17—H170.89 (8)
N1B—HB1B0.8900C18—O191.214 (6)
N1B—HB1C0.8900C18—O201.295 (6)
N7B—C6B1.483 (12)O20—H200.90 (9)
O1A—C1A—O2A126.2 (7)C3B—C2B—C1B109.4 (7)
O1A—C1A—C2A117.7 (7)N1B—C2B—H2B109.4
O2A—C1A—C2A116.0 (6)C3B—C2B—H2B109.4
N1A—C2A—C3A112.3 (7)C1B—C2B—H2B109.4
N1A—C2A—C1A109.4 (6)C4B—C3B—C2B113.7 (9)
C3A—C2A—C1A111.5 (5)C4B—C3B—H3B1108.8
N1A—C2A—H2A107.8C2B—C3B—H3B1108.8
C3A—C2A—H2A107.8C4B—C3B—H3B2108.8
C1A—C2A—H2A107.8C2B—C3B—H3B2108.8
C2A—C3A—C4A116.1 (6)H3B1—C3B—H3B2107.7
C2A—C3A—H3A1108.3C5B—C4B—C3B111.2 (9)
C4A—C3A—H3A1108.3C5B—C4B—H4B1109.4
C2A—C3A—H3A2108.3C3B—C4B—H4B1109.4
C4A—C3A—H3A2108.3C5B—C4B—H4B2109.4
H3A1—C3A—H3A2107.4C3B—C4B—H4B2109.4
C5A—C4A—C3A109.2 (7)H4B1—C4B—H4B2108.0
C5A—C4A—H4A1109.8C4B—C5B—C6B113.3 (9)
C3A—C4A—H4A1109.8C4B—C5B—H5B1108.9
C5A—C4A—H4A2109.8C6B—C5B—H5B1108.9
C3A—C4A—H4A2109.8C4B—C5B—H5B2108.9
H4A1—C4A—H4A2108.3C6B—C5B—H5B2108.9
C6A—C5A—C4A113.9 (7)H5B1—C5B—H5B2107.7
C6A—C5A—H5A1108.8N7B—C6B—C5B109.8 (11)
C4A—C5A—H5A1108.8N7B—C6B—H6B1109.7
C6A—C5A—H5A2108.8C5B—C6B—H6B1109.7
C4A—C5A—H5A2108.8N7B—C6B—H6B2109.7
H5A1—C5A—H5A2107.7C5B—C6B—H6B2109.7
C5A—C6A—N7A111.4 (10)H6B1—C6B—H6B2108.2
C5A—C6A—H6A1109.3O12—C13—O11124.4 (3)
N7A—C6A—H6A1109.3O12—C13—C14117.9 (3)
C5A—C6A—H6A2109.3O11—C13—C14117.7 (3)
N7A—C6A—H6A2109.3O15—C14—C13114.6 (3)
H6A1—C6A—H6A2108.0O15—C14—C16112.3 (3)
C2B—N1B—HB1A109.5C13—C14—C16107.2 (3)
C2B—N1B—HB1B109.5O15—C14—H14107.4
HB1A—N1B—HB1B109.5C13—C14—H14107.4
C2B—N1B—HB1C109.5C16—C14—H14107.4
HB1A—N1B—HB1C109.5C14—O15—H15108 (3)
HB1B—N1B—HB1C109.5O17—C16—C18109.3 (4)
C6B—N7B—HB7A109.5O17—C16—C14111.0 (3)
C6B—N7B—HB7B109.5C18—C16—C14109.6 (3)
HB7A—N7B—HB7B109.5O17—C16—H16109.0
C6B—N7B—HB7C109.5C18—C16—H16109.0
HB7A—N7B—HB7C109.5C14—C16—H16109.0
HB7B—N7B—HB7C109.5C16—O17—H17116 (5)
O1B—C1B—O2B125.8 (9)O19—C18—O20124.5 (4)
O1B—C1B—C2B116.5 (9)O19—C18—C16122.9 (4)
O2B—C1B—C2B115.4 (8)O20—C18—C16112.6 (4)
N1B—C2B—C3B110.7 (10)C18—O20—H20113 (6)
N1B—C2B—C1B108.5 (7)
O1A—C1A—C2A—N1A16.2 (15)C2B—C3B—C4B—C5B161.1 (14)
O2A—C1A—C2A—N1A160.7 (10)C3B—C4B—C5B—C6B172.4 (15)
O1A—C1A—C2A—C3A108.6 (13)C4B—C5B—C6B—N7B135 (2)
O2A—C1A—C2A—C3A74.5 (11)O12—C13—C14—O15161.2 (4)
N1A—C2A—C3A—C4A75.2 (10)O11—C13—C14—O1520.6 (5)
C1A—C2A—C3A—C4A47.9 (10)O12—C13—C14—C1673.4 (4)
C2A—C3A—C4A—C5A177.4 (8)O11—C13—C14—C16104.9 (4)
C3A—C4A—C5A—C6A178.6 (9)O15—C14—C16—O1773.5 (4)
C4A—C5A—C6A—N7A176.0 (11)C13—C14—C16—O1753.3 (4)
O1B—C1B—C2B—N1B51 (2)O15—C14—C16—C1847.3 (4)
O2B—C1B—C2B—N1B144.9 (17)C13—C14—C16—C18174.1 (3)
O1B—C1B—C2B—C3B70 (2)O17—C16—C18—O198.2 (6)
O2B—C1B—C2B—C3B94.2 (16)C14—C16—C18—O19113.7 (5)
N1B—C2B—C3B—C4B179.5 (15)O17—C16—C18—O20172.0 (4)
C1B—C2B—C3B—C4B60.0 (16)C14—C16—C18—O2066.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—HA1B···O12i0.892.452.870 (11)110
N1A—HA1B···O17ii0.892.323.119 (13)149
N1A—HA1C···O19iii0.891.972.862 (13)177
N7A—HA7A···O12iv0.892.413.16 (2)141
N7A—HA7B···O2Av0.891.922.72 (3)149
N7A—HA7C···O1Avi0.892.323.10 (2)145
N7A—HA7C···O2Avi0.892.022.79 (2)145
O15—H15···O12vii0.84 (5)1.93 (5)2.736 (4)160 (4)
O17—H17···O1Avi0.89 (8)1.86 (8)2.742 (12)172 (7)
O20—H20···O11i0.90 (9)1.63 (9)2.533 (4)175 (9)
N1B—HB1A···O12i0.892.002.753 (19)142
N1B—HB1B···O17ii0.892.042.884 (19)157
N1B—HB1C···O19iii0.891.952.80 (2)160
N7B—HB7A···O2Bvi0.892.163.02 (3)162
N7B—HB7B···O11viii0.891.922.71 (2)146
N7B—HB7C···O2Bv0.892.363.17 (4)151
O17—H17···O1Bvi0.89 (8)1.82 (8)2.678 (18)164 (7)
Symmetry codes: (i) x, y, z1; (ii) x1, y, z1; (iii) x1, y, z; (iv) x, y+1/2, z+2; (v) x+1, y, z+1; (vi) x, y, z+1; (vii) x+1, y, z; (viii) x+1, y+1/2, z+2.

Experimental details

(I)(II)(III)(IV)
Crystal data
Chemical formulaC6H15N4O2+·C4H5O62(C6H15N4O2)+·C4H4O622(C6H15N4O2)+·C4H4O62·H2OC6H15N2O2+·C4H5O6
Mr324.30498.51460.49296.28
Crystal system, space groupTriclinic, P1Monoclinic, P21Monoclinic, P21/cMonoclinic, P21
Temperature (K)2982982982983
a, b, c (Å)5.4876 (16), 10.021 (3), 13.868 (4)9.907 (2), 8.7428 (18), 14.076 (3)10.087 (3), 23.003 (8), 9.414 (3)5.1849 (11), 16.667 (4), 7.6701 (17)
α, β, γ (°)109.079 (5), 94.378 (5), 94.538 (5)90, 109.412 (3), 9090, 90.820 (7), 9090, 96.366 (4), 90
V3)714.3 (4)1149.9 (4)2184.2 (13)658.7 (2)
Z2242
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.130.120.120.13
Crystal size (mm)0.25 × 0.2 × 0.10.42 × 0.27 × 0.150.47 × 0.10 × 0.070.4 × 0.35 × 0.2
Data collection
DiffractometerBruker SMART CCD area detector
diffractometer
Bruker SMART CCD area detector
diffractometer
Bruker SMART CCD area detector
diffractometer
Bruker SMART CCD area detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6914, 2504, 1543 8353, 2162, 2054 15605, 3842, 2876 4251, 1342, 1231
Rint0.0570.0160.0460.025
(sin θ/λ)max1)0.5950.5950.5950.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.132, 1.07 0.034, 0.088, 1.06 0.071, 0.218, 1.10 0.040, 0.090, 1.13
No. of reflections2508216238421342
No. of parameters260380379242
No. of restraints5227279
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.230.37, 0.170.75, 0.300.15, 0.16


(V)
Crystal data
Chemical formulaC6H15N2O2+·C4H5O6
Mr296.28
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)5.1022 (11), 17.444 (4), 7.547 (2)
α, β, γ (°)90, 97.748 (4), 90
V3)665.6 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.35 × 0.25 × 0.20
Data collection
DiffractometerBruker SMART CCD area detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3396, 1200, 1146
Rint0.028
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.116, 1.13
No. of reflections1200
No. of parameters288
No. of restraints303
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.19

Computer programs: Bruker SMART, Bruker SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and pyMOL (DeLano, 2002), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i1.06 (5)1.74 (5)2.788 (4)169 (3)
N1—H1B···O170.82 (4)2.21 (4)3.001 (4)160 (3)
N1—H1C···O1ii1.04 (6)2.29 (6)3.171 (4)141 (4)
N1—H1C···O2ii1.04 (6)2.31 (6)3.300 (4)159 (4)
N6—H6···O190.84 (4)2.11 (4)2.892 (4)155 (4)
N8—H8A···O2iii0.96 (4)1.91 (4)2.807 (4)155 (3)
N8—H8B···O11iv0.92 (4)1.89 (4)2.801 (4)174 (4)
N9—H9A···O12iv0.85 (4)2.25 (4)3.099 (4)176 (3)
N9—H9B···O190.89 (4)2.34 (4)3.111 (5)145 (3)
N9—H9B···O20v0.89 (4)2.33 (4)2.976 (4)129 (3)
O12—H12···O12vi1.2251.2252.451 (4)180
O15—H15···O1i0.91 (5)2.02 (5)2.813 (3)144 (4)
O17—H17···O20vii0.822.132.953 (4)178
O20—H20···O20v1.2331.2332.466 (4)180
Symmetry codes: (i) x, y+1, z+2; (ii) x1, y+1, z+2; (iii) x, y+2, z+2; (iv) x+1, y+1, z; (v) x+1, y+1, z+1; (vi) x, y, z+1; (vii) x1, y, z.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O210.89 (4)2.01 (4)2.892 (3)171 (3)
N1—H1B···O110.94 (3)1.82 (4)2.759 (3)177 (3)
N1—H1C···O22i0.91 (3)1.86 (3)2.770 (3)176 (3)
N6—H6···O27i0.90 (3)1.91 (3)2.785 (3)164 (3)
N8—H8A···O12ii0.82 (4)2.16 (4)2.961 (4)167 (4)
N8—H8B···O21iii0.84 (3)2.15 (3)2.934 (3)155 (3)
N9—H9A···O29i0.86 (4)2.30 (4)3.130 (4)162 (3)
N9—H9B···O21iii0.88 (4)2.33 (4)3.127 (4)151 (3)
N11—H11A···O10.84 (4)2.22 (4)3.046 (3)166 (4)
N11—H11B···O30iv0.93 (3)1.81 (3)2.732 (3)170 (3)
N11—H11C···O290.92 (5)1.99 (5)2.906 (4)176 (3)
N16—H16···O2v0.89 (3)1.92 (3)2.781 (3)162 (3)
N18—H18A···O1vi0.89 (3)2.00 (4)2.863 (3)165 (3)
N18—H18B···O29vii0.99 (4)1.86 (4)2.840 (3)168 (3)
N19—H19A···O2v0.90 (4)2.03 (4)2.841 (4)149 (3)
N19—H19B···O29vii0.90 (5)2.52 (5)3.224 (4)136 (4)
O25—H25···O10.832.232.840 (3)131
O27—H27···O110.86 (5)1.89 (5)2.698 (4)155 (4)
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x1, y, z; (iii) x, y+1/2, z+1; (iv) x+2, y+1/2, z+2; (v) x+2, y1/2, z+2; (vi) x+1, y, z; (vii) x+3, y+1/2, z+2.
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30i0.99 (5)1.90 (5)2.879 (4)168 (4)
N1—H1B···O11ii1.02 (5)2.00 (5)2.938 (5)151 (4)
N1—H1C···O2iii1.06 (5)1.75 (5)2.794 (4)165 (4)
N7—H7A···O12iv0.96 (6)1.90 (6)2.852 (5)169 (5)
N7—H7B···O211.02 (6)1.77 (6)2.774 (4)169 (5)
N7—H7C···O1W0.90 (4)2.06 (4)2.950 (9)172 (4)
N7—H7C···O2W0.90 (4)2.30 (4)2.956 (9)130 (3)
N11—H11A···O1v0.87 (5)2.36 (5)3.146 (5)149 (3)
N11—H11A···O2vi0.87 (5)2.44 (4)3.061 (4)129 (3)
N11—H11B···O210.84 (5)2.09 (6)2.868 (4)155 (5)
N11—H11B···O250.84 (5)2.31 (5)2.929 (4)131 (4)
N11—H11C···O12iii0.90 (5)1.98 (5)2.872 (5)174 (4)
N17—H17A···O27vii0.85 (6)2.24 (5)2.926 (4)138 (4)
N17—H17A···O29vii0.85 (6)2.25 (6)2.983 (5)144 (4)
N17—H17B···O30viii0.98 (6)1.94 (6)2.915 (5)169 (4)
N17—H17C···O20.78 (5)2.20 (5)2.972 (5)176 (4)
O25—H25···O29ix0.88 (6)1.85 (6)2.708 (4)164 (5)
O27—H27···O22x0.821.902.702 (4)167.0
O3W—O29···2.904 (1)xi3_756O3WO1W3.030 (2)
Symmetry codes: (i) x+1, y, z+1; (ii) x1, y+1/2, z+1/2; (iii) x, y+1/2, z+1/2; (iv) x, y, z+1; (v) x+1, y+1/2, z1/2; (vi) x+1, y, z; (vii) x1, y, z; (viii) x+1, y, z; (ix) x+2, y, z; (x) x+2, y, z+1; (xi) x+1, y, z+2.
Hydrogen-bond geometry (Å, º) for (IV) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O12i0.89 (4)2.22 (4)2.959 (4)141 (3)
N1—H1A···O17ii0.89 (4)2.38 (4)3.001 (4)127 (3)
N1—H1B···O19iii0.91 (4)1.99 (4)2.890 (4)169 (4)
N1—H1C···O2Aiv0.86 (5)2.00 (5)2.849 (6)169 (4)
N7—H7A···O2Av1.01 (4)1.67 (5)2.675 (5)174 (4)
N7—H7B···O11v0.84 (5)2.08 (5)2.870 (4)156 (4)
N7—H7C···O12vi0.91 (6)2.38 (5)3.095 (4)135 (4)
O15—H15···O12iv0.87 (5)1.95 (5)2.808 (4)170 (5)
O17—H17···O2Avii0.822.473.230 (7)154.8
O20—H20···O11v0.96 (5)1.57 (5)2.528 (3)171 (5)
Symmetry codes: (i) x+1, y+1/2, z; (ii) x, y+1/2, z; (iii) x, y+1/2, z+1; (iv) x1, y, z; (v) x, y, z+1; (vi) x1, y, z+1; (vii) x+1, y1/2, z.
Hydrogen-bond geometry (Å, º) for (V) top
D—H···AD—HH···AD···AD—H···A
N1A—HA1B···O12i0.892.452.870 (11)109.5
N1A—HA1B···O17ii0.892.323.119 (13)148.6
N1A—HA1C···O19iii0.891.972.862 (13)177.3
N7A—HA7A···O12iv0.892.413.16 (2)141.2
N7A—HA7B···O2Av0.891.922.72 (3)149.1
N7A—HA7C···O1Avi0.892.323.10 (2)145.4
N7A—HA7C···O2Avi0.892.022.79 (2)144.8
O15—H15···O12vii0.84 (5)1.93 (5)2.736 (4)160 (4)
O17—H17···O1Avi0.89 (8)1.86 (8)2.742 (12)172 (7)
O20—H20···O11i0.90 (9)1.63 (9)2.533 (4)175 (9)
N1B—HB1A···O12i0.892.002.753 (19)141.9
N1B—HB1B···O17ii0.892.042.884 (19)156.8
N1B—HB1C···O19iii0.891.952.80 (2)159.6
N7B—HB7A···O2Bvi0.892.163.02 (3)162.0
N7B—HB7B···O11viii0.891.922.71 (2)146.1
N7B—HB7C···O2Bv0.892.363.17 (4)151.4
O17—H17···O1Bvi0.89 (8)1.82 (8)2.678 (18)164 (7)
Symmetry codes: (i) x, y, z1; (ii) x1, y, z1; (iii) x1, y, z; (iv) x, y+1/2, z+2; (v) x+1, y, z+1; (vi) x, y, z+1; (vii) x+1, y, z; (viii) x+1, y+1/2, z+2.
 

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