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
CCDC references: 650652; 650653; 650654; 650655; 650656
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).
(I) DL-arginine DL-tartaric acid complex
top
Crystal data top
C6H15N4O2+·C4H5O6− | Z = 2 |
Mr = 324.30 | F(000) = 344 |
Triclinic, P1 | Dx = 1.508 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.4876 (16) Å | Cell parameters from 835 reflections |
b = 10.021 (3) Å | θ = 1.6–22.0° |
c = 13.868 (4) Å | µ = 0.13 mm−1 |
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 tube | Rint = 0.057 |
Graphite monochromator | θmax = 25.0°, θmin = 1.6° |
ϕ and ω scan | h = −6→6 |
6914 measured reflections | k = −11→11 |
2504 independent reflections | l = −16→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H 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 parameters | Δρmax = 0.27 e Å−3 |
52 restraints | Δρmin = −0.23 e Å−3 |
Crystal data top
C6H15N4O2+·C4H5O6− | γ = 94.538 (5)° |
Mr = 324.30 | V = 714.3 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.4876 (16) Å | Mo Kα radiation |
b = 10.021 (3) Å | µ = 0.13 mm−1 |
c = 13.868 (4) Å | T = 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 reflections | Rint = 0.057 |
2504 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.062 | 52 restraints |
wR(F2) = 0.132 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.27 e Å−3 |
2508 reflections | Δρmin = −0.23 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | −0.2455 (4) | 0.5905 (3) | 1.06068 (17) | 0.0411 (7) | |
O2 | −0.4559 (5) | 0.7503 (3) | 1.02198 (19) | 0.0514 (8) | |
N1 | −0.2269 (6) | 0.4379 (3) | 0.8647 (3) | 0.0343 (8) | |
C1 | −0.3313 (7) | 0.6486 (4) | 1.0000 (3) | 0.0342 (9) | |
C2 | −0.2778 (7) | 0.5878 (3) | 0.8884 (3) | 0.0362 (9) | |
H2 | −0.4174 | 0.5940 | 0.8422 | 0.043* | |
C3A | −0.0414 (7) | 0.6684 (4) | 0.8713 (3) | 0.0310 (11) | 0.824 (5) |
H31 | 0.0862 | 0.6806 | 0.9268 | 0.037* | 0.824 (5) |
H32 | 0.0174 | 0.6140 | 0.8074 | 0.037* | 0.824 (5) |
C4A | −0.0980 (8) | 0.8141 (4) | 0.8672 (4) | 0.0404 (12) | 0.824 (5) |
H41 | −0.1745 | 0.8637 | 0.9276 | 0.048* | 0.824 (5) |
H42 | −0.2126 | 0.8013 | 0.8072 | 0.048* | 0.824 (5) |
C3B | −0.191 (3) | 0.7027 (16) | 0.8434 (13) | 0.036 (3) | 0.176 (5) |
H33 | −0.3088 | 0.7718 | 0.8522 | 0.043* | 0.176 (5) |
H34 | −0.1795 | 0.6595 | 0.7705 | 0.043* | 0.176 (5) |
C4B | 0.062 (3) | 0.7771 (14) | 0.8984 (14) | 0.043 (4) | 0.176 (5) |
H43 | 0.1838 | 0.7099 | 0.8835 | 0.051* | 0.176 (5) |
H44 | 0.0550 | 0.8111 | 0.9721 | 0.051* | 0.176 (5) |
C5 | 0.1386 (7) | 0.9033 (4) | 0.8623 (3) | 0.0492 (11) | |
H5A | 0.1056 | 1.0006 | 0.8734 | 0.059* | |
H5B | 0.2625 | 0.9037 | 0.9161 | 0.059* | |
N6 | 0.2305 (6) | 0.8457 (3) | 0.7630 (2) | 0.0409 (8) | |
C7 | 0.4125 (6) | 0.9127 (3) | 0.7339 (3) | 0.0319 (8) | |
N8 | 0.5122 (6) | 1.0401 (3) | 0.7914 (3) | 0.0436 (9) | |
N9 | 0.4972 (7) | 0.8496 (4) | 0.6445 (3) | 0.0482 (10) | |
O11 | −0.0430 (4) | 0.1521 (3) | 0.74693 (17) | 0.0411 (7) | |
O12 | −0.0821 (5) | 0.0195 (2) | 0.58267 (17) | 0.0437 (7) | |
C13 | 0.0104 (6) | 0.1294 (3) | 0.6593 (3) | 0.0285 (8) | |
C14 | 0.1883 (6) | 0.2390 (3) | 0.6389 (2) | 0.0256 (8) | |
H14 | 0.3060 | 0.1896 | 0.5940 | 0.031* | |
O15 | 0.3187 (4) | 0.3330 (2) | 0.73050 (18) | 0.0363 (6) | |
C16 | 0.0435 (6) | 0.3222 (3) | 0.5845 (2) | 0.0300 (8) | |
H16 | −0.0234 | 0.2584 | 0.5160 | 0.036* | |
O17 | −0.1547 (5) | 0.3708 (3) | 0.6421 (2) | 0.0421 (7) | |
C18 | 0.2080 (7) | 0.4443 (4) | 0.5737 (2) | 0.0333 (9) | |
O19 | 0.1640 (5) | 0.5675 (2) | 0.60692 (18) | 0.0459 (7) | |
O20 | 0.3959 (5) | 0.4042 (2) | 0.52453 (19) | 0.0472 (7) | |
H1A | −0.055 (9) | 0.431 (4) | 0.902 (3) | 0.074 (14)* | |
H1B | −0.220 (7) | 0.399 (4) | 0.803 (3) | 0.050 (12)* | |
H1C | −0.365 (11) | 0.387 (5) | 0.892 (4) | 0.118 (19)* | |
H6 | 0.168 (9) | 0.766 (5) | 0.724 (3) | 0.078 (16)* | |
H8A | 0.450 (7) | 1.094 (4) | 0.853 (3) | 0.065 (13)* | |
H8B | 0.651 (8) | 1.080 (4) | 0.774 (3) | 0.057 (12)* | |
H9A | 0.618 (7) | 0.893 (4) | 0.628 (3) | 0.045 (12)* | |
H9B | 0.445 (7) | 0.758 (4) | 0.611 (3) | 0.054 (12)* | |
H12 | 0.0000 | 0.0000 | 0.5000 | 0.11 (2)* | |
H15 | 0.244 (9) | 0.326 (5) | 0.785 (3) | 0.103 (19)* | |
H17 | −0.278 (6) | 0.380 (5) | 0.609 (3) | 0.078 (17)* | |
H20 | 0.5000 | 0.5000 | 0.5000 | 0.12 (3)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0400 (16) | 0.0502 (16) | 0.0269 (14) | −0.0064 (12) | 0.0063 (12) | 0.0066 (12) |
O2 | 0.0517 (18) | 0.0457 (17) | 0.0461 (17) | 0.0105 (14) | 0.0163 (14) | −0.0026 (13) |
N1 | 0.034 (2) | 0.0391 (19) | 0.0218 (17) | −0.0022 (15) | 0.0081 (16) | −0.0009 (15) |
C1 | 0.032 (2) | 0.033 (2) | 0.029 (2) | −0.0128 (17) | 0.0088 (17) | 0.0003 (18) |
C2 | 0.048 (2) | 0.028 (2) | 0.0281 (19) | −0.0039 (17) | 0.0091 (17) | 0.0045 (16) |
C3A | 0.032 (3) | 0.033 (2) | 0.030 (2) | 0.007 (2) | 0.014 (2) | 0.0104 (19) |
C4A | 0.038 (3) | 0.039 (3) | 0.049 (3) | 0.005 (2) | 0.013 (2) | 0.019 (2) |
C3B | 0.039 (6) | 0.032 (6) | 0.036 (6) | 0.012 (6) | 0.010 (6) | 0.008 (5) |
C4B | 0.040 (6) | 0.042 (6) | 0.041 (6) | 0.002 (6) | 0.015 (6) | 0.005 (6) |
C5 | 0.058 (3) | 0.037 (2) | 0.046 (2) | −0.010 (2) | 0.025 (2) | 0.0034 (19) |
N6 | 0.047 (2) | 0.0312 (19) | 0.0366 (19) | −0.0121 (16) | 0.0156 (16) | 0.0024 (16) |
C7 | 0.034 (2) | 0.027 (2) | 0.032 (2) | 0.0021 (16) | 0.0062 (17) | 0.0065 (16) |
N8 | 0.044 (2) | 0.0290 (18) | 0.049 (2) | −0.0086 (16) | 0.0234 (17) | 0.0002 (16) |
N9 | 0.062 (3) | 0.033 (2) | 0.041 (2) | −0.0107 (18) | 0.0239 (18) | −0.0002 (17) |
O11 | 0.0449 (16) | 0.0461 (15) | 0.0306 (14) | −0.0101 (12) | 0.0141 (12) | 0.0117 (12) |
O12 | 0.0581 (18) | 0.0310 (14) | 0.0339 (15) | −0.0142 (12) | 0.0142 (13) | 0.0024 (12) |
C13 | 0.0274 (19) | 0.0270 (19) | 0.033 (2) | 0.0031 (15) | 0.0082 (16) | 0.0116 (16) |
C14 | 0.0242 (18) | 0.0266 (18) | 0.0263 (18) | 0.0008 (15) | 0.0078 (15) | 0.0087 (15) |
O15 | 0.0351 (15) | 0.0453 (15) | 0.0236 (13) | −0.0118 (11) | −0.0019 (11) | 0.0098 (12) |
C16 | 0.033 (2) | 0.032 (2) | 0.0212 (17) | 0.0000 (16) | 0.0043 (15) | 0.0039 (15) |
O17 | 0.0283 (15) | 0.0570 (18) | 0.0421 (16) | 0.0113 (13) | 0.0048 (13) | 0.0164 (13) |
C18 | 0.050 (2) | 0.026 (2) | 0.0233 (18) | 0.0014 (18) | 0.0027 (17) | 0.0080 (15) |
O19 | 0.0632 (19) | 0.0235 (15) | 0.0461 (16) | 0.0031 (13) | 0.0116 (14) | 0.0040 (12) |
O20 | 0.0643 (19) | 0.0348 (15) | 0.0523 (16) | 0.0094 (13) | 0.0333 (15) | 0.0210 (13) |
Geometric parameters (Å, º) top
O1—C1 | 1.254 (4) | C5—H5B | 0.9700 |
O2—C1 | 1.240 (4) | N6—C7 | 1.320 (4) |
N1—C2 | 1.483 (5) | N6—H6 | 0.84 (4) |
N1—H1A | 1.06 (5) | C7—N8 | 1.313 (4) |
N1—H1B | 0.82 (4) | C7—N9 | 1.332 (4) |
N1—H1C | 1.04 (6) | N8—H8A | 0.96 (4) |
C1—C2 | 1.527 (5) | N8—H8B | 0.92 (4) |
C2—C3B | 1.540 (5) | N9—H9A | 0.85 (4) |
C2—C3A | 1.549 (4) | N9—H9B | 0.89 (4) |
C2—H2 | 0.9800 | O11—C13 | 1.224 (4) |
C3A—C4A | 1.534 (4) | O12—C13 | 1.290 (4) |
C3A—H31 | 0.9700 | O12—H12 | 1.225 |
C3A—H32 | 0.9700 | C13—C14 | 1.522 (4) |
C4A—C5 | 1.536 (4) | C14—O15 | 1.409 (4) |
C4A—H41 | 0.9700 | C14—C16 | 1.523 (5) |
C4A—H42 | 0.9700 | C14—H14 | 0.9800 |
C3B—C4B | 1.540 (5) | O15—H15 | 0.91 (5) |
C3B—H33 | 0.9700 | C16—O17 | 1.422 (4) |
C3B—H34 | 0.9700 | C16—C18 | 1.517 (5) |
C4B—C5 | 1.546 (5) | C16—H16 | 0.9800 |
C4B—H43 | 0.9700 | O17—H17 | 0.82 (2) |
C4B—H44 | 0.9700 | C18—O19 | 1.219 (4) |
C5—N6 | 1.454 (4) | C18—O20 | 1.298 (4) |
C5—H5A | 0.9700 | O20—H20 | 1.233 |
| | | |
C2—N1—H1A | 111 (2) | N6—C5—C4A | 110.6 (3) |
C2—N1—H1B | 111 (3) | N6—C5—C4B | 107.6 (8) |
H1A—N1—H1B | 106 (3) | N6—C5—H5A | 109.5 |
C2—N1—H1C | 107 (3) | C4A—C5—H5A | 109.5 |
H1A—N1—H1C | 109 (3) | N6—C5—H5B | 109.5 |
H1B—N1—H1C | 112 (4) | C4A—C5—H5B | 109.5 |
O2—C1—O1 | 126.1 (3) | C4B—C5—H5B | 72.1 |
O2—C1—C2 | 117.1 (4) | H5A—C5—H5B | 108.1 |
O1—C1—C2 | 116.8 (3) | C7—N6—C5 | 122.7 (3) |
N1—C2—C1 | 109.9 (3) | C7—N6—H6 | 119 (3) |
N1—C2—C3B | 131.6 (8) | C5—N6—H6 | 118 (3) |
C1—C2—C3B | 113.3 (8) | N8—C7—N6 | 121.3 (3) |
N1—C2—C3A | 105.9 (3) | N8—C7—N9 | 119.3 (3) |
C1—C2—C3A | 110.3 (3) | N6—C7—N9 | 119.4 (3) |
N1—C2—H2 | 110.2 | C7—N8—H8A | 123 (2) |
C1—C2—H2 | 110.2 | C7—N8—H8B | 120 (2) |
C3B—C2—H2 | 74.0 | H8A—N8—H8B | 117 (3) |
C3A—C2—H2 | 110.2 | C7—N9—H9A | 118 (2) |
C4A—C3A—C2 | 109.4 (3) | C7—N9—H9B | 118 (2) |
C4A—C3A—H31 | 109.8 | H9A—N9—H9B | 123 (3) |
C2—C3A—H31 | 109.8 | C13—O12—H12 | 118.3 |
C4A—C3A—H32 | 109.8 | O11—C13—O12 | 123.4 (3) |
C2—C3A—H32 | 109.8 | O11—C13—C14 | 118.4 (3) |
H31—C3A—H32 | 108.2 | O12—C13—C14 | 118.2 (3) |
C3A—C4A—C5 | 110.6 (3) | O15—C14—C13 | 111.6 (2) |
C3A—C4A—H41 | 109.5 | O15—C14—C16 | 109.7 (3) |
C5—C4A—H41 | 109.5 | C13—C14—C16 | 108.8 (3) |
C3A—C4A—H42 | 109.5 | O15—C14—H14 | 108.9 |
C5—C4A—H42 | 109.5 | C13—C14—H14 | 108.9 |
H41—C4A—H42 | 108.1 | C16—C14—H14 | 108.9 |
C2—C3B—C4B | 109.5 (8) | C14—O15—H15 | 110 (3) |
C2—C3B—H33 | 109.8 | O17—C16—C18 | 111.7 (3) |
C4B—C3B—H33 | 109.8 | O17—C16—C14 | 107.7 (3) |
C2—C3B—H34 | 109.8 | C18—C16—C14 | 110.7 (3) |
C4B—C3B—H34 | 109.8 | O17—C16—H16 | 108.9 |
H33—C3B—H34 | 108.2 | C18—C16—H16 | 108.9 |
C3B—C4B—C5 | 110.0 (8) | C14—C16—H16 | 108.9 |
C3B—C4B—H43 | 109.7 | C16—O17—H17 | 115 (3) |
C5—C4B—H43 | 109.7 | O19—C18—O20 | 123.8 (3) |
C3B—C4B—H44 | 109.7 | O19—C18—C16 | 122.8 (3) |
C5—C4B—H44 | 109.7 | O20—C18—C16 | 113.4 (3) |
H43—C4B—H44 | 108.2 | C18—O20—H20 | 112.0 |
| | | |
O2—C1—C2—N1 | −155.9 (3) | C4B—C5—N6—C7 | −145.1 (7) |
O1—C1—C2—N1 | 24.0 (4) | C5—N6—C7—N8 | −4.0 (6) |
O2—C1—C2—C3B | 46.6 (8) | C5—N6—C7—N9 | 175.9 (4) |
O1—C1—C2—C3B | −133.6 (8) | O11—C13—C14—O15 | 16.5 (4) |
O2—C1—C2—C3A | 87.8 (4) | O12—C13—C14—O15 | −165.6 (3) |
O1—C1—C2—C3A | −92.4 (4) | O11—C13—C14—C16 | −104.7 (3) |
N1—C2—C3A—C4A | 165.7 (3) | O12—C13—C14—C16 | 73.2 (4) |
C1—C2—C3A—C4A | −75.5 (4) | O15—C14—C16—O17 | −71.5 (3) |
C2—C3A—C4A—C5 | 173.7 (3) | C13—C14—C16—O17 | 50.8 (3) |
N1—C2—C3B—C4B | −84.8 (16) | O15—C14—C16—C18 | 50.9 (3) |
C1—C2—C3B—C4B | 66.5 (16) | C13—C14—C16—C18 | 173.3 (3) |
C2—C3B—C4B—C5 | −173.9 (11) | O17—C16—C18—O19 | −3.3 (5) |
C3A—C4A—C5—N6 | 70.5 (5) | C14—C16—C18—O19 | −123.4 (3) |
C3B—C4B—C5—N6 | −79.1 (15) | O17—C16—C18—O20 | 177.8 (3) |
C4A—C5—N6—C7 | 170.9 (4) | C14—C16—C18—O20 | 57.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 1.06 (5) | 1.74 (5) | 2.788 (4) | 169 (3) |
N1—H1B···O17 | 0.82 (4) | 2.21 (4) | 3.001 (4) | 160 (3) |
N1—H1C···O1ii | 1.04 (6) | 2.29 (6) | 3.171 (4) | 141 (4) |
N1—H1C···O2ii | 1.04 (6) | 2.31 (6) | 3.300 (4) | 159 (4) |
N6—H6···O19 | 0.84 (4) | 2.11 (4) | 2.892 (4) | 155 (4) |
N8—H8A···O2iii | 0.96 (4) | 1.91 (4) | 2.807 (4) | 155 (3) |
N8—H8B···O11iv | 0.92 (4) | 1.89 (4) | 2.801 (4) | 174 (4) |
N9—H9A···O12iv | 0.85 (4) | 2.25 (4) | 3.099 (4) | 176 (3) |
N9—H9B···O19 | 0.89 (4) | 2.34 (4) | 3.111 (5) | 145 (3) |
N9—H9B···O20v | 0.89 (4) | 2.33 (4) | 2.976 (4) | 129 (3) |
O12—H12···O12vi | 1.23 | 1.23 | 2.451 (4) | 180 |
O15—H15···O1i | 0.91 (5) | 2.02 (5) | 2.813 (3) | 144 (4) |
O17—H17···O20vii | 0.82 | 2.13 | 2.953 (4) | 178 |
O20—H20···O20v | 1.23 | 1.23 | 2.466 (4) | 180 |
Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x−1, −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) x−1, y, z. |
(II)
L-arginine
L-tartaric acid complex
top
Crystal data top
2(C6H15N4O2)+·C4H4O62− | F(000) = 532 |
Mr = 498.51 | Dx = 1.440 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 1374 reflections |
a = 9.907 (2) Å | θ = 1.5–25.0° |
b = 8.7428 (18) Å | µ = 0.12 mm−1 |
c = 14.076 (3) Å | T = 298 K |
β = 109.412 (3)° | Plate, colourless |
V = 1149.9 (4) Å3 | 0.42 × 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 tube | Rint = 0.016 |
Graphite monochromator | θmax = 25.0°, θmin = 1.5° |
ϕ and ω scan | h = −11→11 |
8353 measured reflections | k = −10→9 |
2162 independent reflections | l = −16→16 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H 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 reflections | Δρmax = 0.37 e Å−3 |
380 parameters | Δρmin = −0.17 e Å−3 |
2 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0074 (19) |
Crystal data top
2(C6H15N4O2)+·C4H4O62− | V = 1149.9 (4) Å3 |
Mr = 498.51 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.907 (2) Å | µ = 0.12 mm−1 |
b = 8.7428 (18) Å | T = 298 K |
c = 14.076 (3) Å | 0.42 × 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 reflections | Rint = 0.016 |
2162 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.034 | 2 restraints |
wR(F2) = 0.088 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.37 e Å−3 |
2162 reflections | Δρmin = −0.17 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.6385 (2) | 0.3214 (2) | 0.80456 (14) | 0.0372 (5) | |
O2 | 0.4988 (2) | 0.5225 (3) | 0.79604 (15) | 0.0513 (6) | |
N1 | 0.5701 (2) | 0.2930 (3) | 0.60514 (16) | 0.0281 (5) | |
C1 | 0.5556 (3) | 0.4243 (3) | 0.75787 (18) | 0.0292 (5) | |
C2 | 0.5218 (3) | 0.4347 (3) | 0.64353 (18) | 0.0272 (5) | |
H2 | 0.5767 | 0.5205 | 0.6304 | 0.033* | |
C3 | 0.3639 (3) | 0.4659 (3) | 0.58693 (18) | 0.0319 (6) | |
H3A | 0.3359 | 0.5594 | 0.6125 | 0.038* | |
H3B | 0.3507 | 0.4814 | 0.5162 | 0.038* | |
C4 | 0.2674 (3) | 0.3360 (4) | 0.5972 (2) | 0.0411 (7) | |
H4A | 0.2712 | 0.2543 | 0.5515 | 0.049* | |
H4B | 0.3043 | 0.2958 | 0.6652 | 0.049* | |
C5 | 0.1129 (3) | 0.3821 (5) | 0.5754 (2) | 0.0437 (8) | |
H5A | 0.0617 | 0.2990 | 0.5939 | 0.052* | |
H5B | 0.1088 | 0.4703 | 0.6161 | 0.052* | |
N6 | 0.0434 (2) | 0.4192 (3) | 0.46961 (17) | 0.0386 (6) | |
C7 | −0.0955 (3) | 0.4425 (4) | 0.4291 (2) | 0.0343 (6) | |
N8 | −0.1806 (3) | 0.4440 (4) | 0.4843 (2) | 0.0475 (7) | |
N9 | −0.1526 (3) | 0.4666 (4) | 0.33043 (18) | 0.0439 (7) | |
O11 | 0.8614 (2) | 0.2550 (3) | 0.69469 (15) | 0.0465 (6) | |
O12 | 0.9239 (3) | 0.4992 (3) | 0.70440 (18) | 0.0654 (8) | |
N11 | 0.9510 (3) | 0.2266 (4) | 0.89608 (18) | 0.0351 (6) | |
C11 | 0.9236 (3) | 0.3724 (4) | 0.7406 (2) | 0.0428 (8) | |
C12 | 1.0153 (3) | 0.3497 (4) | 0.8512 (2) | 0.0377 (7) | |
H12 | 1.0222 | 0.4454 | 0.8888 | 0.045* | |
C13 | 1.1643 (3) | 0.3000 (4) | 0.8503 (2) | 0.0413 (7) | |
H13A | 1.1529 | 0.2096 | 0.8083 | 0.050* | |
H13B | 1.2023 | 0.3806 | 0.8190 | 0.050* | |
C14 | 1.2733 (3) | 0.2651 (4) | 0.9523 (2) | 0.0435 (7) | |
H14A | 1.2378 | 0.1844 | 0.9851 | 0.052* | |
H14B | 1.2901 | 0.3554 | 0.9946 | 0.052* | |
C15 | 1.4115 (3) | 0.2148 (5) | 0.9375 (2) | 0.0497 (8) | |
H15A | 1.3936 | 0.1272 | 0.8928 | 0.060* | |
H15B | 1.4486 | 0.2971 | 0.9070 | 0.060* | |
N16 | 1.5155 (3) | 0.1749 (4) | 1.03412 (18) | 0.0466 (7) | |
C17 | 1.6460 (3) | 0.2285 (4) | 1.0709 (2) | 0.0359 (6) | |
N18 | 1.7052 (3) | 0.3150 (4) | 1.0187 (2) | 0.0445 (7) | |
N19 | 1.7213 (3) | 0.1958 (4) | 1.1672 (2) | 0.0529 (8) | |
O21 | 0.4623 (2) | 0.0132 (3) | 0.66299 (17) | 0.0444 (5) | |
O22 | 0.5159 (2) | −0.2058 (3) | 0.60332 (15) | 0.0441 (5) | |
C23 | 0.5371 (3) | −0.1060 (3) | 0.66868 (19) | 0.0305 (6) | |
C24 | 0.6650 (3) | −0.1278 (3) | 0.76652 (18) | 0.0290 (6) | |
H24 | 0.6454 | −0.2162 | 0.8027 | 0.035* | |
O25 | 0.6877 (2) | 0.0017 (2) | 0.83055 (14) | 0.0365 (5) | |
C26 | 0.7999 (3) | −0.1605 (3) | 0.74077 (18) | 0.0302 (6) | |
H26 | 0.7883 | −0.2606 | 0.7077 | 0.036* | |
O27 | 0.8179 (2) | −0.0494 (3) | 0.67198 (14) | 0.0387 (5) | |
C28 | 0.9295 (3) | −0.1695 (3) | 0.83744 (19) | 0.0322 (6) | |
O29 | 1.0307 (2) | −0.0753 (3) | 0.84651 (17) | 0.0479 (6) | |
O30 | 0.9270 (2) | −0.2697 (3) | 0.89899 (14) | 0.0436 (5) | |
H1A | 0.527 (3) | 0.211 (4) | 0.619 (2) | 0.028 (7)* | |
H1B | 0.669 (4) | 0.278 (5) | 0.634 (2) | 0.048 (9)* | |
H1C | 0.545 (3) | 0.298 (4) | 0.537 (2) | 0.035 (8)* | |
H6 | 0.101 (3) | 0.418 (4) | 0.432 (2) | 0.042 (9)* | |
H8A | −0.148 (4) | 0.445 (5) | 0.546 (3) | 0.045 (9)* | |
H8B | −0.269 (4) | 0.445 (4) | 0.454 (2) | 0.032 (8)* | |
H9A | −0.100 (4) | 0.458 (5) | 0.293 (3) | 0.060 (11)* | |
H9B | −0.246 (4) | 0.480 (5) | 0.309 (3) | 0.058 (11)* | |
H11A | 0.862 (4) | 0.238 (5) | 0.875 (3) | 0.050 (10)* | |
H11B | 0.988 (3) | 0.217 (4) | 0.966 (2) | 0.043 (9)* | |
H11C | 0.977 (4) | 0.134 (5) | 0.878 (3) | 0.055 (11)* | |
H16 | 1.495 (3) | 0.116 (4) | 1.080 (2) | 0.037 (8)* | |
H18A | 1.670 (3) | 0.326 (4) | 0.952 (3) | 0.045 (9)* | |
H18B | 1.802 (4) | 0.352 (5) | 1.058 (3) | 0.053 (10)* | |
H19A | 1.676 (3) | 0.141 (5) | 1.202 (3) | 0.049 (9)* | |
H19B | 1.816 (5) | 0.213 (6) | 1.184 (3) | 0.082 (14)* | |
H25 | 0.627 (3) | 0.067 (4) | 0.802 (2) | 0.051 (11)* | |
H27 | 0.841 (4) | 0.040 (6) | 0.698 (3) | 0.054 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0387 (10) | 0.0469 (12) | 0.0238 (9) | 0.0092 (10) | 0.0073 (8) | 0.0036 (9) |
O2 | 0.0635 (14) | 0.0573 (15) | 0.0324 (11) | 0.0204 (12) | 0.0149 (10) | −0.0043 (10) |
N1 | 0.0258 (11) | 0.0335 (13) | 0.0228 (11) | 0.0013 (10) | 0.0054 (9) | 0.0011 (10) |
C1 | 0.0262 (11) | 0.0341 (14) | 0.0254 (12) | −0.0020 (12) | 0.0061 (10) | −0.0014 (11) |
C2 | 0.0262 (12) | 0.0276 (13) | 0.0260 (12) | −0.0007 (11) | 0.0063 (10) | 0.0016 (10) |
C3 | 0.0306 (13) | 0.0355 (15) | 0.0260 (13) | 0.0036 (12) | 0.0046 (10) | 0.0032 (11) |
C4 | 0.0268 (14) | 0.0496 (19) | 0.0441 (17) | 0.0047 (13) | 0.0081 (12) | 0.0134 (14) |
C5 | 0.0268 (13) | 0.069 (2) | 0.0345 (15) | 0.0055 (14) | 0.0097 (11) | 0.0151 (16) |
N6 | 0.0248 (10) | 0.0620 (17) | 0.0294 (11) | 0.0048 (12) | 0.0095 (9) | 0.0076 (12) |
C7 | 0.0273 (12) | 0.0422 (16) | 0.0323 (14) | 0.0010 (12) | 0.0085 (11) | 0.0025 (13) |
N8 | 0.0216 (11) | 0.087 (2) | 0.0309 (13) | 0.0034 (14) | 0.0052 (10) | 0.0097 (14) |
N9 | 0.0341 (13) | 0.0660 (19) | 0.0284 (12) | 0.0022 (13) | 0.0062 (10) | 0.0024 (13) |
O11 | 0.0364 (10) | 0.0700 (17) | 0.0285 (10) | 0.0032 (11) | 0.0048 (9) | −0.0009 (11) |
O12 | 0.102 (2) | 0.0561 (15) | 0.0474 (13) | 0.0320 (15) | 0.0369 (14) | 0.0156 (12) |
N11 | 0.0247 (12) | 0.0541 (17) | 0.0238 (12) | −0.0006 (11) | 0.0045 (9) | −0.0020 (11) |
C11 | 0.0423 (16) | 0.055 (2) | 0.0377 (16) | 0.0255 (16) | 0.0227 (13) | 0.0132 (16) |
C12 | 0.0337 (14) | 0.0401 (16) | 0.0348 (15) | 0.0045 (13) | 0.0055 (12) | 0.0024 (13) |
C13 | 0.0375 (15) | 0.0504 (18) | 0.0354 (15) | −0.0042 (14) | 0.0114 (12) | 0.0021 (14) |
C14 | 0.0368 (15) | 0.055 (2) | 0.0376 (16) | 0.0000 (14) | 0.0104 (13) | 0.0020 (14) |
C15 | 0.0295 (14) | 0.073 (2) | 0.0467 (17) | −0.0026 (15) | 0.0121 (13) | 0.0046 (17) |
N16 | 0.0369 (13) | 0.0676 (19) | 0.0345 (13) | −0.0149 (13) | 0.0108 (11) | 0.0080 (13) |
C17 | 0.0360 (14) | 0.0428 (16) | 0.0286 (13) | −0.0071 (13) | 0.0106 (11) | −0.0039 (12) |
N18 | 0.0348 (13) | 0.0676 (19) | 0.0282 (13) | −0.0163 (13) | 0.0069 (10) | −0.0008 (13) |
N19 | 0.0464 (15) | 0.070 (2) | 0.0355 (14) | −0.0186 (15) | 0.0041 (12) | 0.0059 (14) |
O21 | 0.0260 (9) | 0.0392 (12) | 0.0571 (13) | 0.0015 (9) | −0.0009 (9) | 0.0086 (10) |
O22 | 0.0497 (12) | 0.0426 (12) | 0.0285 (10) | −0.0086 (10) | −0.0025 (9) | −0.0001 (10) |
C23 | 0.0249 (12) | 0.0323 (14) | 0.0297 (13) | −0.0044 (11) | 0.0031 (10) | 0.0072 (12) |
C24 | 0.0278 (13) | 0.0340 (13) | 0.0217 (12) | 0.0018 (11) | 0.0037 (10) | 0.0015 (11) |
O25 | 0.0354 (10) | 0.0408 (12) | 0.0280 (10) | 0.0070 (9) | 0.0034 (8) | −0.0069 (9) |
C26 | 0.0321 (13) | 0.0350 (15) | 0.0217 (12) | 0.0029 (12) | 0.0068 (10) | −0.0034 (11) |
O27 | 0.0406 (11) | 0.0524 (13) | 0.0243 (9) | −0.0025 (10) | 0.0123 (8) | 0.0012 (10) |
C28 | 0.0283 (13) | 0.0409 (16) | 0.0250 (13) | 0.0099 (12) | 0.0058 (10) | −0.0055 (12) |
O29 | 0.0295 (10) | 0.0553 (14) | 0.0489 (12) | 0.0007 (11) | −0.0005 (9) | −0.0013 (11) |
O30 | 0.0434 (12) | 0.0530 (13) | 0.0265 (10) | 0.0083 (10) | 0.0010 (9) | 0.0030 (10) |
Geometric parameters (Å, º) top
O1—C1 | 1.248 (3) | C12—C13 | 1.544 (4) |
O2—C1 | 1.242 (3) | C12—H12 | 0.9800 |
N1—C2 | 1.493 (4) | C13—C14 | 1.513 (4) |
N1—H1A | 0.89 (4) | C13—H13A | 0.9700 |
N1—H1B | 0.94 (3) | C13—H13B | 0.9700 |
N1—H1C | 0.91 (3) | C14—C15 | 1.517 (4) |
C1—C2 | 1.534 (3) | C14—H14A | 0.9700 |
C2—C3 | 1.525 (3) | C14—H14B | 0.9700 |
C2—H2 | 0.9800 | C15—N16 | 1.450 (4) |
C3—C4 | 1.523 (4) | C15—H15A | 0.9700 |
C3—H3A | 0.9700 | C15—H15B | 0.9700 |
C3—H3B | 0.9700 | N16—C17 | 1.310 (4) |
C4—C5 | 1.512 (4) | N16—H16 | 0.89 (3) |
C4—H4A | 0.9700 | C17—N18 | 1.321 (4) |
C4—H4B | 0.9700 | C17—N19 | 1.343 (4) |
C5—N6 | 1.454 (4) | N18—H18A | 0.89 (3) |
C5—H5A | 0.9700 | N18—H18B | 0.99 (4) |
C5—H5B | 0.9700 | N19—H19A | 0.90 (4) |
N6—C7 | 1.319 (3) | N19—H19B | 0.90 (5) |
N6—H6 | 0.90 (3) | O21—C23 | 1.265 (4) |
C7—N8 | 1.323 (4) | O22—C23 | 1.234 (4) |
C7—N9 | 1.331 (4) | C23—C24 | 1.542 (3) |
N8—H8A | 0.82 (4) | C24—O25 | 1.417 (3) |
N8—H8B | 0.84 (3) | C24—C26 | 1.524 (3) |
N9—H9A | 0.86 (4) | C24—H24 | 0.9800 |
N9—H9B | 0.88 (4) | O25—H25 | 0.83 (2) |
O11—C11 | 1.260 (4) | C26—O27 | 1.424 (3) |
O12—C11 | 1.221 (4) | C26—C28 | 1.531 (3) |
N11—C12 | 1.494 (4) | C26—H26 | 0.9800 |
N11—H11A | 0.84 (4) | O27—H27 | 0.86 (5) |
N11—H11B | 0.93 (3) | C28—O30 | 1.238 (4) |
N11—H11C | 0.92 (5) | C28—O29 | 1.271 (4) |
C11—C12 | 1.532 (4) | | |
| | | |
C2—N1—H1A | 110.5 (19) | N11—C12—C13 | 110.2 (3) |
C2—N1—H1B | 112 (2) | C11—C12—C13 | 105.9 (2) |
H1A—N1—H1B | 108 (3) | N11—C12—H12 | 110.5 |
C2—N1—H1C | 110 (2) | C11—C12—H12 | 110.5 |
H1A—N1—H1C | 107 (3) | C13—C12—H12 | 110.5 |
H1B—N1—H1C | 110 (3) | C14—C13—C12 | 115.6 (2) |
O2—C1—O1 | 125.7 (2) | C14—C13—H13A | 108.4 |
O2—C1—C2 | 116.1 (2) | C12—C13—H13A | 108.4 |
O1—C1—C2 | 118.1 (2) | C14—C13—H13B | 108.4 |
N1—C2—C3 | 110.8 (2) | C12—C13—H13B | 108.4 |
N1—C2—C1 | 110.2 (2) | H13A—C13—H13B | 107.5 |
C3—C2—C1 | 112.8 (2) | C13—C14—C15 | 108.6 (2) |
N1—C2—H2 | 107.6 | C13—C14—H14A | 110.0 |
C3—C2—H2 | 107.6 | C15—C14—H14A | 110.0 |
C1—C2—H2 | 107.6 | C13—C14—H14B | 110.0 |
C4—C3—C2 | 112.6 (2) | C15—C14—H14B | 110.0 |
C4—C3—H3A | 109.1 | H14A—C14—H14B | 108.3 |
C2—C3—H3A | 109.1 | N16—C15—C14 | 109.4 (2) |
C4—C3—H3B | 109.1 | N16—C15—H15A | 109.8 |
C2—C3—H3B | 109.1 | C14—C15—H15A | 109.8 |
H3A—C3—H3B | 107.8 | N16—C15—H15B | 109.8 |
C5—C4—C3 | 114.0 (3) | C14—C15—H15B | 109.8 |
C5—C4—H4A | 108.8 | H15A—C15—H15B | 108.2 |
C3—C4—H4A | 108.8 | C17—N16—C15 | 125.8 (3) |
C5—C4—H4B | 108.8 | C17—N16—H16 | 111 (2) |
C3—C4—H4B | 108.8 | C15—N16—H16 | 123 (2) |
H4A—C4—H4B | 107.6 | N16—C17—N18 | 123.2 (3) |
N6—C5—C4 | 111.7 (2) | N16—C17—N19 | 117.9 (3) |
N6—C5—H5A | 109.3 | N18—C17—N19 | 118.9 (3) |
C4—C5—H5A | 109.3 | C17—N18—H18A | 124 (2) |
N6—C5—H5B | 109.3 | C17—N18—H18B | 114 (2) |
C4—C5—H5B | 109.3 | H18A—N18—H18B | 121 (3) |
H5A—C5—H5B | 107.9 | C17—N19—H19A | 117 (2) |
C7—N6—C5 | 123.2 (2) | C17—N19—H19B | 114 (3) |
C7—N6—H6 | 121 (2) | H19A—N19—H19B | 128 (4) |
C5—N6—H6 | 115 (2) | O22—C23—O21 | 125.7 (2) |
N6—C7—N8 | 121.7 (3) | O22—C23—C24 | 117.6 (2) |
N6—C7—N9 | 119.8 (2) | O21—C23—C24 | 116.6 (2) |
N8—C7—N9 | 118.6 (3) | O25—C24—C26 | 109.5 (2) |
C7—N8—H8A | 122 (2) | O25—C24—C23 | 112.3 (2) |
C7—N8—H8B | 118 (2) | C26—C24—C23 | 109.6 (2) |
H8A—N8—H8B | 120 (3) | O25—C24—H24 | 108.4 |
C7—N9—H9A | 120 (2) | C26—C24—H24 | 108.4 |
C7—N9—H9B | 115 (2) | C23—C24—H24 | 108.4 |
H9A—N9—H9B | 125 (4) | C24—O25—H25 | 108 (3) |
C12—N11—H11A | 108 (3) | O27—C26—C24 | 110.6 (2) |
C12—N11—H11B | 116 (2) | O27—C26—C28 | 112.5 (2) |
H11A—N11—H11B | 112 (3) | C24—C26—C28 | 109.9 (2) |
C12—N11—H11C | 109 (2) | O27—C26—H26 | 107.9 |
H11A—N11—H11C | 112 (4) | C24—C26—H26 | 107.9 |
H11B—N11—H11C | 99 (3) | C28—C26—H26 | 107.9 |
O12—C11—O11 | 126.5 (3) | C26—O27—H27 | 114 (3) |
O12—C11—C12 | 117.3 (3) | O30—C28—O29 | 125.9 (2) |
O11—C11—C12 | 116.1 (3) | O30—C28—C26 | 116.9 (2) |
N11—C12—C11 | 109.3 (2) | O29—C28—C26 | 117.1 (2) |
| | | |
O2—C1—C2—N1 | −167.9 (2) | C12—C13—C14—C15 | 178.7 (3) |
O1—C1—C2—N1 | 13.4 (3) | C13—C14—C15—N16 | −177.7 (3) |
O2—C1—C2—C3 | −43.4 (3) | C14—C15—N16—C17 | −127.5 (4) |
O1—C1—C2—C3 | 137.9 (3) | C15—N16—C17—N18 | −7.7 (5) |
N1—C2—C3—C4 | 59.8 (3) | C15—N16—C17—N19 | 171.0 (3) |
C1—C2—C3—C4 | −64.4 (3) | O22—C23—C24—O25 | 173.4 (2) |
C2—C3—C4—C5 | 159.6 (2) | O21—C23—C24—O25 | −7.0 (3) |
C3—C4—C5—N6 | 68.1 (4) | O22—C23—C24—C26 | 51.4 (3) |
C4—C5—N6—C7 | 170.5 (3) | O21—C23—C24—C26 | −129.0 (3) |
C5—N6—C7—N8 | 4.8 (5) | O25—C24—C26—O27 | −72.9 (3) |
C5—N6—C7—N9 | −175.8 (3) | C23—C24—C26—O27 | 50.7 (3) |
O12—C11—C12—N11 | 151.9 (3) | O25—C24—C26—C28 | 51.9 (3) |
O11—C11—C12—N11 | −31.8 (3) | C23—C24—C26—C28 | 175.5 (2) |
O12—C11—C12—C13 | −89.4 (3) | O27—C26—C28—O30 | −175.7 (2) |
O11—C11—C12—C13 | 86.8 (3) | C24—C26—C28—O30 | 60.6 (3) |
N11—C12—C13—C14 | −59.8 (4) | O27—C26—C28—O29 | 3.2 (3) |
C11—C12—C13—C14 | −177.9 (3) | C24—C26—C28—O29 | −120.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O21 | 0.89 (4) | 2.01 (4) | 2.892 (3) | 171 (3) |
N1—H1B···O11 | 0.94 (3) | 1.82 (4) | 2.759 (3) | 177 (3) |
N1—H1C···O22i | 0.91 (3) | 1.86 (3) | 2.770 (3) | 176 (3) |
N6—H6···O27i | 0.90 (3) | 1.91 (3) | 2.785 (3) | 164 (3) |
N8—H8A···O12ii | 0.82 (4) | 2.16 (4) | 2.961 (4) | 167 (4) |
N8—H8B···O21iii | 0.84 (3) | 2.15 (3) | 2.934 (3) | 155 (3) |
N9—H9A···O29i | 0.86 (4) | 2.30 (4) | 3.130 (4) | 162 (3) |
N9—H9B···O21iii | 0.88 (4) | 2.33 (4) | 3.127 (4) | 151 (3) |
N11—H11A···O1 | 0.84 (4) | 2.22 (4) | 3.046 (3) | 166 (4) |
N11—H11B···O30iv | 0.93 (3) | 1.81 (3) | 2.732 (3) | 170 (3) |
N11—H11C···O29 | 0.92 (5) | 1.99 (5) | 2.906 (4) | 176 (3) |
N16—H16···O2v | 0.89 (3) | 1.92 (3) | 2.781 (3) | 162 (3) |
N18—H18A···O1vi | 0.89 (3) | 2.00 (4) | 2.863 (3) | 165 (3) |
N18—H18B···O29vii | 0.99 (4) | 1.86 (4) | 2.840 (3) | 168 (3) |
N19—H19A···O2v | 0.90 (4) | 2.03 (4) | 2.841 (4) | 149 (3) |
N19—H19B···O29vii | 0.90 (5) | 2.52 (5) | 3.224 (4) | 136 (4) |
O25—H25···O1 | 0.83 | 2.23 | 2.840 (3) | 131 |
O27—H27···O11 | 0.86 (5) | 1.89 (5) | 2.698 (4) | 155 (4) |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) x−1, y, z; (iii) −x, y+1/2, −z+1; (iv) −x+2, y+1/2, −z+2; (v) −x+2, y−1/2, −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−·H2O | F(000) = 992 |
Mr = 460.49 | Dx = 1.400 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 732 reflections |
a = 10.087 (3) Å | θ = 2.2–21.5° |
b = 23.003 (8) Å | µ = 0.12 mm−1 |
c = 9.414 (3) Å | T = 298 K |
β = 90.820 (7)° | Needle, colourless |
V = 2184.2 (13) Å3 | 0.47 × 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 tube | Rint = 0.046 |
Graphite monochromator | θmax = 25.0°, θmin = 1.8° |
ϕ and ω scan | h = −11→11 |
15605 measured reflections | k = −27→27 |
3842 independent reflections | l = −11→11 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.071 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.218 | H 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 parameters | Δρmax = 0.75 e Å−3 |
72 restraints | Δρmin = −0.30 e Å−3 |
Crystal data top
2(C6H15N4O2)+·C4H4O62−·H2O | V = 2184.2 (13) Å3 |
Mr = 460.49 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.087 (3) Å | µ = 0.12 mm−1 |
b = 23.003 (8) Å | T = 298 K |
c = 9.414 (3) Å | 0.47 × 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 reflections | Rint = 0.046 |
3842 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.071 | 72 restraints |
wR(F2) = 0.218 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.75 e Å−3 |
3842 reflections | Δρmin = −0.30 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.0134 (3) | 0.27407 (11) | 0.4861 (3) | 0.0379 (7) | |
O2 | 0.0506 (3) | 0.21428 (11) | 0.3055 (3) | 0.0354 (7) | |
N1 | −0.0413 (3) | 0.18627 (14) | 0.6650 (3) | 0.0292 (7) | |
C1 | 0.0305 (3) | 0.22528 (15) | 0.4347 (4) | 0.0249 (8) | |
C2 | 0.0281 (4) | 0.17145 (15) | 0.5310 (4) | 0.0266 (8) | |
H2 | −0.0230 | 0.1410 | 0.4821 | 0.032* | |
C3 | 0.1655 (4) | 0.14802 (16) | 0.5622 (4) | 0.0298 (8) | |
H3A | 0.2043 | 0.1356 | 0.4736 | 0.036* | |
H3B | 0.1577 | 0.1140 | 0.6224 | 0.036* | |
C4 | 0.2591 (4) | 0.19074 (19) | 0.6339 (5) | 0.0434 (11) | |
H4A | 0.2147 | 0.2084 | 0.7139 | 0.052* | |
H4B | 0.2802 | 0.2214 | 0.5673 | 0.052* | |
C5 | 0.3889 (4) | 0.1624 (2) | 0.6870 (4) | 0.0403 (10) | |
H5A | 0.4359 | 0.1898 | 0.7477 | 0.048* | |
H5B | 0.3674 | 0.1287 | 0.7442 | 0.048* | |
C6 | 0.4792 (4) | 0.14372 (19) | 0.5696 (4) | 0.0384 (10) | |
H6A | 0.4374 | 0.1127 | 0.5153 | 0.046* | |
H6B | 0.4939 | 0.1762 | 0.5060 | 0.046* | |
N7 | 0.6089 (3) | 0.12301 (17) | 0.6284 (4) | 0.0361 (8) | |
O11 | 0.7280 (3) | 0.27196 (11) | 0.0007 (3) | 0.0388 (7) | |
O12 | 0.6893 (3) | 0.21413 (12) | −0.1837 (3) | 0.0394 (7) | |
N11 | 0.7798 (4) | 0.18248 (15) | 0.1768 (3) | 0.0275 (7) | |
C11 | 0.7100 (3) | 0.22335 (16) | −0.0534 (4) | 0.0271 (8) | |
C12 | 0.7115 (4) | 0.16932 (17) | 0.0403 (4) | 0.0334 (9) | |
H12 | 0.7677 | 0.1410 | −0.0081 | 0.040* | |
C13A | 0.5804 (4) | 0.1386 (2) | 0.0653 (5) | 0.0310 (12) | 0.764 (7) |
H13A | 0.5950 | 0.1048 | 0.1253 | 0.037* | 0.764 (7) |
H13B | 0.5430 | 0.1255 | −0.0246 | 0.037* | 0.764 (7) |
C14A | 0.4837 (4) | 0.1803 (2) | 0.1371 (6) | 0.0396 (13) | 0.764 (7) |
H14A | 0.4636 | 0.2120 | 0.0724 | 0.047* | 0.764 (7) |
H14B | 0.5266 | 0.1967 | 0.2208 | 0.047* | 0.764 (7) |
C15A | 0.3529 (5) | 0.1512 (3) | 0.1813 (5) | 0.0366 (14) | 0.764 (7) |
H15A | 0.3740 | 0.1170 | 0.2374 | 0.044* | 0.764 (7) |
H15B | 0.3053 | 0.1780 | 0.2418 | 0.044* | 0.764 (7) |
C13B | 0.5638 (7) | 0.1712 (7) | 0.076 (2) | 0.041 (3) | 0.236 (7) |
H13C | 0.5156 | 0.1747 | −0.0139 | 0.049* | 0.236 (7) |
H13D | 0.5489 | 0.2069 | 0.1276 | 0.049* | 0.236 (7) |
C14B | 0.4973 (13) | 0.1222 (7) | 0.1595 (17) | 0.036 (2) | 0.236 (7) |
H14C | 0.5440 | 0.1189 | 0.2500 | 0.044* | 0.236 (7) |
H14D | 0.5126 | 0.0862 | 0.1085 | 0.044* | 0.236 (7) |
C15B | 0.3483 (12) | 0.1252 (10) | 0.1912 (10) | 0.033 (4) | 0.236 (7) |
H15C | 0.3224 | 0.0897 | 0.2389 | 0.040* | 0.236 (7) |
H15D | 0.3328 | 0.1573 | 0.2556 | 0.040* | 0.236 (7) |
C16 | 0.2610 (4) | 0.13317 (19) | 0.0588 (4) | 0.0384 (10) | |
H16A | 0.2577 | 0.1642 | −0.0110 | 0.046* | |
H16B | 0.2973 | 0.0990 | 0.0132 | 0.046* | |
N17 | 0.1247 (3) | 0.12019 (16) | 0.1053 (4) | 0.0280 (7) | |
O21 | 0.7543 (3) | 0.09446 (11) | 0.3905 (3) | 0.0373 (7) | |
O22 | 0.7501 (3) | 0.00534 (12) | 0.4799 (3) | 0.0377 (7) | |
C23 | 0.7810 (3) | 0.04184 (16) | 0.3854 (4) | 0.0259 (8) | |
C24 | 0.8552 (3) | 0.01767 (14) | 0.2566 (4) | 0.0241 (8) | |
H24 | 0.8050 | −0.0153 | 0.2178 | 0.029* | |
O25 | 0.8629 (3) | 0.06098 (11) | 0.1511 (3) | 0.0297 (6) | |
C26 | 0.9936 (3) | −0.00365 (14) | 0.3015 (3) | 0.0222 (7) | |
H26 | 0.9848 | −0.0308 | 0.3811 | 0.027* | |
O27 | 1.0669 (3) | 0.04550 (10) | 0.3483 (2) | 0.0285 (6) | |
H27 | 1.1293 | 0.0348 | 0.3987 | 0.034* | |
C28 | 1.0578 (4) | −0.03539 (15) | 0.1778 (4) | 0.0250 (8) | |
O29 | 1.1434 (3) | −0.00923 (11) | 0.1073 (3) | 0.0353 (7) | |
O30 | 1.0169 (3) | −0.08603 (11) | 0.1534 (3) | 0.0377 (7) | |
O1W | 0.5810 (10) | 0.0235 (4) | 0.8233 (12) | 0.044 (3) | 0.33 |
O2W | 0.5197 (7) | 0.0006 (4) | 0.6244 (9) | 0.043 (2) | 0.34 |
O3W | 0.5695 (10) | 0.0083 (5) | 0.9114 (15) | 0.064 (3) | 0.33 |
H1A | −0.042 (5) | 0.154 (2) | 0.735 (5) | 0.057 (13)* | |
H1B | −0.137 (5) | 0.194 (2) | 0.635 (5) | 0.062 (15)* | |
H1C | 0.010 (5) | 0.221 (2) | 0.715 (5) | 0.054 (13)* | |
H7A | 0.647 (5) | 0.151 (2) | 0.693 (5) | 0.064 (15)* | |
H7B | 0.670 (5) | 0.111 (2) | 0.549 (6) | 0.069 (16)* | |
H7C | 0.593 (4) | 0.0920 (18) | 0.684 (4) | 0.028 (11)* | |
H11A | 0.862 (5) | 0.1893 (16) | 0.153 (4) | 0.031 (11)* | |
H11B | 0.788 (5) | 0.151 (2) | 0.222 (6) | 0.063 (16)* | |
H11C | 0.749 (5) | 0.213 (2) | 0.225 (5) | 0.042 (12)* | |
H17A | 0.130 (5) | 0.087 (2) | 0.146 (5) | 0.057 (15)* | |
H17B | 0.069 (5) | 0.106 (2) | 0.026 (6) | 0.065 (15)* | |
H17C | 0.102 (4) | 0.144 (2) | 0.158 (5) | 0.035 (13)* | |
H25 | 0.877 (5) | 0.043 (2) | 0.071 (6) | 0.070 (17)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0555 (18) | 0.0255 (15) | 0.0327 (15) | 0.0007 (12) | −0.0053 (13) | −0.0008 (11) |
O2 | 0.0471 (17) | 0.0356 (15) | 0.0237 (14) | 0.0048 (12) | 0.0051 (11) | 0.0014 (11) |
N1 | 0.0334 (19) | 0.0283 (17) | 0.0260 (17) | −0.0004 (14) | 0.0043 (13) | 0.0036 (14) |
C1 | 0.0247 (18) | 0.0265 (19) | 0.0233 (18) | −0.0009 (15) | −0.0030 (14) | −0.0004 (15) |
C2 | 0.0282 (19) | 0.0277 (19) | 0.0240 (18) | 0.0021 (15) | 0.0009 (14) | 0.0001 (15) |
C3 | 0.030 (2) | 0.029 (2) | 0.030 (2) | 0.0037 (16) | 0.0012 (16) | 0.0000 (15) |
C4 | 0.036 (2) | 0.040 (2) | 0.055 (3) | 0.0038 (19) | −0.006 (2) | −0.009 (2) |
C5 | 0.029 (2) | 0.054 (3) | 0.037 (2) | 0.0042 (19) | −0.0030 (17) | −0.0097 (19) |
C6 | 0.031 (2) | 0.051 (3) | 0.032 (2) | 0.0005 (18) | −0.0031 (17) | −0.0059 (18) |
N7 | 0.0295 (19) | 0.040 (2) | 0.038 (2) | 0.0032 (15) | 0.0045 (16) | −0.0058 (18) |
O11 | 0.0478 (17) | 0.0312 (15) | 0.0375 (16) | 0.0026 (12) | 0.0004 (13) | 0.0006 (12) |
O12 | 0.0528 (18) | 0.0418 (16) | 0.0236 (15) | −0.0088 (13) | −0.0070 (12) | 0.0064 (12) |
N11 | 0.0286 (19) | 0.0261 (18) | 0.0277 (17) | −0.0011 (15) | −0.0020 (14) | 0.0024 (15) |
C11 | 0.0212 (18) | 0.031 (2) | 0.029 (2) | −0.0014 (15) | 0.0005 (14) | 0.0030 (16) |
C12 | 0.039 (2) | 0.037 (2) | 0.0243 (19) | −0.0091 (17) | −0.0016 (16) | 0.0019 (16) |
C13A | 0.036 (3) | 0.021 (3) | 0.036 (3) | −0.007 (2) | −0.003 (2) | 0.001 (2) |
C14A | 0.035 (3) | 0.036 (3) | 0.048 (3) | −0.005 (2) | −0.004 (2) | −0.009 (2) |
C15A | 0.031 (3) | 0.041 (4) | 0.039 (3) | −0.006 (3) | 0.005 (2) | −0.006 (3) |
C13B | 0.041 (6) | 0.041 (6) | 0.041 (5) | −0.016 (6) | 0.001 (5) | 0.004 (6) |
C14B | 0.032 (4) | 0.037 (5) | 0.040 (5) | −0.006 (4) | 0.003 (4) | −0.001 (4) |
C15B | 0.025 (6) | 0.041 (8) | 0.034 (6) | −0.008 (6) | 0.006 (5) | −0.003 (6) |
C16 | 0.033 (2) | 0.050 (2) | 0.032 (2) | 0.0003 (18) | 0.0088 (17) | −0.0022 (18) |
N17 | 0.0280 (18) | 0.0235 (18) | 0.0326 (19) | −0.0012 (14) | 0.0012 (15) | 0.0008 (16) |
O21 | 0.0492 (17) | 0.0300 (15) | 0.0331 (15) | 0.0115 (12) | 0.0129 (12) | 0.0011 (11) |
O22 | 0.0365 (16) | 0.0429 (16) | 0.0339 (15) | 0.0074 (12) | 0.0103 (12) | 0.0153 (12) |
C23 | 0.0220 (18) | 0.029 (2) | 0.0264 (19) | 0.0027 (15) | 0.0016 (14) | 0.0030 (15) |
C24 | 0.0301 (19) | 0.0196 (17) | 0.0228 (18) | 0.0002 (14) | −0.0008 (14) | −0.0001 (14) |
O25 | 0.0445 (16) | 0.0259 (14) | 0.0189 (13) | 0.0085 (11) | 0.0026 (11) | 0.0030 (10) |
C26 | 0.0293 (19) | 0.0176 (17) | 0.0199 (16) | −0.0016 (14) | 0.0024 (14) | 0.0015 (13) |
O27 | 0.0340 (15) | 0.0258 (13) | 0.0256 (13) | −0.0021 (10) | −0.0052 (11) | −0.0020 (10) |
C28 | 0.033 (2) | 0.0216 (18) | 0.0208 (17) | 0.0047 (15) | −0.0003 (14) | 0.0037 (14) |
O29 | 0.0407 (16) | 0.0359 (15) | 0.0298 (15) | −0.0046 (12) | 0.0127 (12) | −0.0033 (11) |
O30 | 0.065 (2) | 0.0197 (14) | 0.0281 (14) | −0.0012 (12) | 0.0071 (13) | −0.0030 (11) |
O1W | 0.031 (5) | 0.045 (6) | 0.058 (6) | 0.008 (4) | 0.008 (5) | 0.037 (5) |
O2W | 0.022 (4) | 0.055 (5) | 0.052 (5) | −0.007 (4) | 0.016 (4) | 0.014 (4) |
O3W | 0.026 (5) | 0.063 (8) | 0.102 (10) | −0.009 (5) | 0.017 (6) | −0.045 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.235 (4) | C13A—H13B | 0.9700 |
O2—C1 | 1.261 (4) | C14A—C15A | 1.542 (5) |
N1—C2 | 1.491 (4) | C14A—H14A | 0.9700 |
N1—H1A | 0.99 (5) | C14A—H14B | 0.9700 |
N1—H1B | 1.02 (5) | C15A—C16 | 1.527 (5) |
N1—H1C | 1.06 (5) | C15A—H15A | 0.9700 |
C1—C2 | 1.535 (5) | C15A—H15B | 0.9700 |
C2—C3 | 1.512 (5) | C13B—C14B | 1.536 (6) |
C2—H2 | 0.9800 | C13B—H13C | 0.9700 |
C3—C4 | 1.515 (5) | C13B—H13D | 0.9700 |
C3—H3A | 0.9700 | C14B—C15B | 1.538 (6) |
C3—H3B | 0.9700 | C14B—H14C | 0.9700 |
C4—C5 | 1.540 (6) | C14B—H14D | 0.9700 |
C4—H4A | 0.9700 | C15B—C16 | 1.527 (6) |
C4—H4B | 0.9700 | C15B—H15C | 0.9700 |
C5—C6 | 1.504 (5) | C15B—H15D | 0.9700 |
C5—H5A | 0.9700 | C16—N17 | 1.479 (5) |
C5—H5B | 0.9700 | C16—H16A | 0.9700 |
C6—N7 | 1.492 (5) | C16—H16B | 0.9700 |
C6—H6A | 0.9700 | N17—H17A | 0.85 (6) |
C6—H6B | 0.9700 | N17—H17B | 0.98 (6) |
N7—H7A | 0.96 (6) | N17—H17C | 0.78 (5) |
N7—H7B | 1.02 (6) | O21—C23 | 1.241 (4) |
N7—H7C | 0.90 (4) | O22—C23 | 1.265 (4) |
O11—C11 | 1.241 (4) | C23—C24 | 1.539 (5) |
O12—C11 | 1.259 (4) | C24—O25 | 1.409 (4) |
N11—C12 | 1.481 (5) | C24—C26 | 1.534 (5) |
N11—H11A | 0.87 (5) | C24—H24 | 0.9800 |
N11—H11B | 0.84 (5) | O25—H25 | 0.88 (6) |
N11—H11C | 0.90 (5) | C26—O27 | 1.418 (4) |
C11—C12 | 1.524 (5) | C26—C28 | 1.526 (5) |
C12—C13A | 1.520 (5) | C26—H26 | 0.9800 |
C12—C13B | 1.531 (6) | O27—H27 | 0.8200 |
C12—H12 | 0.9800 | C28—O29 | 1.252 (4) |
C13A—C14A | 1.532 (5) | C28—O30 | 1.256 (4) |
C13A—H13A | 0.9700 | | |
| | | |
C2—N1—H1A | 114 (3) | C14A—C13A—H13B | 109.7 |
C2—N1—H1B | 105 (3) | H13A—C13A—H13B | 108.2 |
H1A—N1—H1B | 108 (4) | C13A—C14A—C15A | 113.6 (4) |
C2—N1—H1C | 109 (3) | C13A—C14A—H14A | 108.8 |
H1A—N1—H1C | 106 (4) | C15A—C14A—H14A | 108.8 |
H1B—N1—H1C | 116 (4) | C13A—C14A—H14B | 108.8 |
O1—C1—O2 | 125.8 (3) | C15A—C14A—H14B | 108.8 |
O1—C1—C2 | 119.9 (3) | H14A—C14A—H14B | 107.7 |
O2—C1—C2 | 114.3 (3) | C16—C15A—C14A | 115.3 (4) |
N1—C2—C3 | 110.9 (3) | C16—C15A—H15A | 108.4 |
N1—C2—C1 | 109.1 (3) | C14A—C15A—H15A | 108.4 |
C3—C2—C1 | 112.3 (3) | C16—C15A—H15B | 108.4 |
N1—C2—H2 | 108.1 | C14A—C15A—H15B | 108.4 |
C3—C2—H2 | 108.1 | H15A—C15A—H15B | 107.5 |
C1—C2—H2 | 108.1 | C12—C13B—C14B | 121.7 (10) |
C2—C3—C4 | 114.8 (3) | C12—C13B—H13C | 106.9 |
C2—C3—H3A | 108.6 | C14B—C13B—H13C | 106.9 |
C4—C3—H3A | 108.6 | C12—C13B—H13D | 106.9 |
C2—C3—H3B | 108.6 | C14B—C13B—H13D | 106.9 |
C4—C3—H3B | 108.6 | H13C—C13B—H13D | 106.7 |
H3A—C3—H3B | 107.5 | C13B—C14B—C15B | 120.1 (12) |
C3—C4—C5 | 113.0 (3) | C13B—C14B—H14C | 107.3 |
C3—C4—H4A | 109.0 | C15B—C14B—H14C | 107.3 |
C5—C4—H4A | 109.0 | C13B—C14B—H14D | 107.3 |
C3—C4—H4B | 109.0 | C15B—C14B—H14D | 107.3 |
C5—C4—H4B | 109.0 | H14C—C14B—H14D | 106.9 |
H4A—C4—H4B | 107.8 | C16—C15B—C14B | 113.7 (10) |
C6—C5—C4 | 113.8 (3) | C16—C15B—H15C | 108.8 |
C6—C5—H5A | 108.8 | C14B—C15B—H15C | 108.8 |
C4—C5—H5A | 108.8 | C16—C15B—H15D | 108.8 |
C6—C5—H5B | 108.8 | C14B—C15B—H15D | 108.8 |
C4—C5—H5B | 108.8 | H15C—C15B—H15D | 107.7 |
H5A—C5—H5B | 107.7 | N17—C16—C15A | 112.8 (3) |
N7—C6—C5 | 110.8 (3) | N17—C16—C15B | 105.2 (6) |
N7—C6—H6A | 109.5 | N17—C16—H16A | 109.0 |
C5—C6—H6A | 109.5 | C15A—C16—H16A | 109.0 |
N7—C6—H6B | 109.5 | C15B—C16—H16A | 130.9 |
C5—C6—H6B | 109.5 | N17—C16—H16B | 109.0 |
H6A—C6—H6B | 108.1 | C15A—C16—H16B | 109.0 |
C6—N7—H7A | 111 (3) | C15B—C16—H16B | 92.7 |
C6—N7—H7B | 111 (3) | H16A—C16—H16B | 107.8 |
H7A—N7—H7B | 114 (4) | C16—N17—H17A | 105 (3) |
C6—N7—H7C | 108 (3) | C16—N17—H17B | 111 (3) |
H7A—N7—H7C | 104 (4) | H17A—N17—H17B | 95 (4) |
H7B—N7—H7C | 108 (4) | C16—N17—H17C | 109 (3) |
C12—N11—H11A | 104 (3) | H17A—N17—H17C | 111 (5) |
C12—N11—H11B | 108 (4) | H17B—N17—H17C | 123 (4) |
H11A—N11—H11B | 102 (4) | O21—C23—O22 | 124.4 (3) |
C12—N11—H11C | 116 (3) | O21—C23—C24 | 119.4 (3) |
H11A—N11—H11C | 109 (4) | O22—C23—C24 | 116.2 (3) |
H11B—N11—H11C | 116 (5) | O25—C24—C26 | 111.2 (3) |
O11—C11—O12 | 125.0 (3) | O25—C24—C23 | 109.4 (3) |
O11—C11—C12 | 119.8 (3) | C26—C24—C23 | 110.5 (3) |
O12—C11—C12 | 115.3 (3) | O25—C24—H24 | 108.6 |
N11—C12—C13A | 110.8 (3) | C26—C24—H24 | 108.6 |
N11—C12—C11 | 109.7 (3) | C23—C24—H24 | 108.6 |
C13A—C12—C11 | 117.9 (3) | C24—O25—H25 | 106 (4) |
N11—C12—C13B | 104.4 (8) | O27—C26—C28 | 113.2 (3) |
C11—C12—C13B | 95.8 (6) | O27—C26—C24 | 107.4 (3) |
N11—C12—H12 | 105.9 | C28—C26—C24 | 109.7 (3) |
C13A—C12—H12 | 105.9 | O27—C26—H26 | 108.8 |
C11—C12—H12 | 105.9 | C28—C26—H26 | 108.8 |
C13B—C12—H12 | 133.7 | C24—C26—H26 | 108.8 |
C12—C13A—C14A | 109.7 (4) | C26—O27—H27 | 109.5 |
C12—C13A—H13A | 109.7 | O29—C28—O30 | 125.2 (3) |
C14A—C13A—H13A | 109.7 | O29—C28—C26 | 118.6 (3) |
C12—C13A—H13B | 109.7 | O30—C28—C26 | 116.2 (3) |
| | | |
O1—C1—C2—N1 | 19.6 (5) | N11—C12—C13B—C14B | −74.1 (17) |
O2—C1—C2—N1 | −160.3 (3) | C11—C12—C13B—C14B | 173.8 (16) |
O1—C1—C2—C3 | −103.8 (4) | C12—C13B—C14B—C15B | −179.2 (14) |
O2—C1—C2—C3 | 76.3 (4) | C13B—C14B—C15B—C16 | 55 (2) |
N1—C2—C3—C4 | −63.5 (4) | C14A—C15A—C16—N17 | −164.9 (4) |
C1—C2—C3—C4 | 58.9 (4) | C14B—C15B—C16—N17 | 166.1 (13) |
C2—C3—C4—C5 | 170.0 (3) | O21—C23—C24—O25 | −9.1 (4) |
C3—C4—C5—C6 | 69.8 (5) | O22—C23—C24—O25 | 170.3 (3) |
C4—C5—C6—N7 | 173.5 (4) | O21—C23—C24—C26 | 113.6 (4) |
O11—C11—C12—N11 | −19.3 (5) | O22—C23—C24—C26 | −67.0 (4) |
O12—C11—C12—N11 | 160.9 (3) | O25—C24—C26—O27 | 56.8 (3) |
O11—C11—C12—C13A | 108.7 (4) | C23—C24—C26—O27 | −64.8 (3) |
O12—C11—C12—C13A | −71.1 (5) | O25—C24—C26—C28 | −66.6 (3) |
O11—C11—C12—C13B | 88.2 (9) | C23—C24—C26—C28 | 171.8 (3) |
O12—C11—C12—C13B | −91.6 (9) | O27—C26—C28—O29 | −18.0 (4) |
N11—C12—C13A—C14A | 67.3 (5) | C24—C26—C28—O29 | 102.0 (4) |
C11—C12—C13A—C14A | −60.1 (5) | O27—C26—C28—O30 | 163.6 (3) |
C12—C13A—C14A—C15A | −173.9 (4) | C24—C26—C28—O30 | −76.5 (4) |
C13A—C14A—C15A—C16 | −69.4 (7) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O30i | 0.99 (5) | 1.90 (5) | 2.879 (4) | 168 (4) |
N1—H1B···O11ii | 1.02 (5) | 2.00 (5) | 2.938 (5) | 151 (4) |
N1—H1C···O2iii | 1.06 (5) | 1.75 (5) | 2.794 (4) | 165 (4) |
N7—H7A···O12iv | 0.96 (6) | 1.90 (6) | 2.852 (5) | 169 (5) |
N7—H7B···O21 | 1.02 (6) | 1.77 (6) | 2.774 (4) | 169 (5) |
N7—H7C···O1W | 0.90 (4) | 2.06 (4) | 2.950 (9) | 172 (4) |
N7—H7C···O2W | 0.90 (4) | 2.30 (4) | 2.956 (9) | 130 (3) |
N11—H11A···O1v | 0.87 (5) | 2.36 (5) | 3.146 (5) | 149 (3) |
N11—H11A···O2vi | 0.87 (5) | 2.44 (4) | 3.061 (4) | 129 (3) |
N11—H11B···O21 | 0.84 (5) | 2.09 (6) | 2.868 (4) | 155 (5) |
N11—H11B···O25 | 0.84 (5) | 2.31 (5) | 2.929 (4) | 131 (4) |
N11—H11C···O12iii | 0.90 (5) | 1.98 (5) | 2.872 (5) | 174 (4) |
N17—H17A···O27vii | 0.85 (6) | 2.24 (5) | 2.926 (4) | 138 (4) |
N17—H17A···O29vii | 0.85 (6) | 2.25 (6) | 2.983 (5) | 144 (4) |
N17—H17B···O30viii | 0.98 (6) | 1.94 (6) | 2.915 (5) | 169 (4) |
N17—H17C···O2 | 0.78 (5) | 2.20 (5) | 2.972 (5) | 176 (4) |
O25—H25···O29ix | 0.88 (6) | 1.85 (6) | 2.708 (4) | 164 (5) |
O27—H27···O22x | 0.82 | 1.90 | 2.702 (4) | 167 |
O3W—O29···2.904 (1)xi | 3_756 | O3W | O1W | 3 (1) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, −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, z−1/2; (vi) x+1, y, z; (vii) x−1, 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+·C4H5O6− | F(000) = 316 |
Mr = 296.28 | Dx = 1.494 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 1435 reflections |
a = 5.1849 (11) Å | θ = 2.4–21.5° |
b = 16.667 (4) Å | µ = 0.13 mm−1 |
c = 7.6701 (17) Å | T = 2983 K |
β = 96.366 (4)° | Plate, colourless |
V = 658.7 (2) Å3 | 0.4 × 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 tube | Rint = 0.025 |
Graphite monochromator | θmax = 26.0°, θmin = 2.4° |
ϕ and ω scan | h = −6→6 |
4251 measured reflections | k = −20→17 |
1342 independent reflections | l = −9→9 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H 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 parameters | Δρmax = 0.15 e Å−3 |
79 restraints | Δρmin = −0.16 e Å−3 |
Crystal data top
C6H15N2O2+·C4H5O6− | V = 658.7 (2) Å3 |
Mr = 296.28 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 5.1849 (11) Å | µ = 0.13 mm−1 |
b = 16.667 (4) Å | T = 2983 K |
c = 7.6701 (17) Å | 0.4 × 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 reflections | Rint = 0.025 |
1342 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.040 | 79 restraints |
wR(F2) = 0.090 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | Δρmax = 0.15 e Å−3 |
1342 reflections | Δρmin = −0.16 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
N7 | 0.3338 (7) | 0.3679 (2) | 0.8340 (4) | 0.0379 (7) | |
C3 | −0.1426 (6) | 0.5083 (2) | 0.3292 (4) | 0.0344 (8) | |
H3A | −0.2058 | 0.5413 | 0.4195 | 0.041* | |
H3B | −0.2673 | 0.4655 | 0.3014 | 0.041* | |
C4 | 0.1164 (6) | 0.4714 (2) | 0.4015 (4) | 0.0335 (7) | |
H4A | 0.1681 | 0.4320 | 0.3191 | 0.040* | |
H4B | 0.2481 | 0.5129 | 0.4147 | 0.040* | |
C5 | 0.0981 (6) | 0.4319 (2) | 0.5762 (4) | 0.0332 (7) | |
H5A | −0.0344 | 0.3905 | 0.5622 | 0.040* | |
H5B | 0.0448 | 0.4715 | 0.6577 | 0.040* | |
C6 | 0.3511 (6) | 0.3947 (2) | 0.6526 (4) | 0.0378 (8) | |
H6A | 0.3917 | 0.3494 | 0.5813 | 0.045* | |
H6B | 0.4897 | 0.4338 | 0.6514 | 0.045* | |
N1 | −0.3834 (6) | 0.5972 (2) | 0.1137 (4) | 0.0347 (7) | |
C1A | −0.0476 (7) | 0.5043 (3) | 0.0209 (6) | 0.0367 (14) | 0.815 (11) |
O1A | −0.2208 (7) | 0.4677 (4) | −0.0683 (6) | 0.0633 (18) | 0.815 (11) |
O2A | 0.1872 (8) | 0.4939 (4) | 0.0151 (7) | 0.0462 (16) | 0.815 (11) |
C2 | −0.1273 (6) | 0.5593 (2) | 0.1655 (4) | 0.0290 (7) | |
H2 | 0.0042 | 0.6012 | 0.1909 | 0.035* | |
C1B | −0.050 (2) | 0.525 (2) | −0.0078 (17) | 0.045 (4) | 0.185 (11) |
O1B | −0.219 (3) | 0.5240 (17) | −0.1343 (15) | 0.057 (5) | 0.185 (11) |
O2B | 0.185 (2) | 0.5208 (17) | −0.019 (2) | 0.041 (5) | 0.185 (11) |
O11 | 0.7396 (4) | 0.25423 (15) | −0.0671 (3) | 0.0367 (6) | |
O12 | 1.1371 (4) | 0.23138 (18) | 0.0588 (3) | 0.0436 (7) | |
C13 | 0.9078 (6) | 0.24863 (18) | 0.0650 (3) | 0.0245 (6) | |
C14 | 0.8172 (6) | 0.26391 (19) | 0.2467 (4) | 0.0263 (7) | |
H14 | 0.9471 | 0.2984 | 0.3120 | 0.032* | |
O15 | 0.5765 (5) | 0.30320 (16) | 0.2419 (3) | 0.0358 (6) | |
C16 | 0.8172 (7) | 0.1839 (2) | 0.3447 (4) | 0.0310 (7) | |
H16 | 0.9924 | 0.1610 | 0.3560 | 0.037* | |
O17 | 0.6431 (5) | 0.13050 (16) | 0.2485 (3) | 0.0478 (7) | |
H17 | 0.7252 | 0.0943 | 0.2078 | 0.057* | |
C18 | 0.7312 (6) | 0.1959 (2) | 0.5264 (4) | 0.0294 (7) | |
O19 | 0.5315 (5) | 0.16599 (17) | 0.5662 (3) | 0.0476 (7) | |
O20 | 0.8893 (4) | 0.23808 (15) | 0.6323 (3) | 0.0367 (6) | |
H1A | −0.371 (7) | 0.629 (3) | 0.023 (5) | 0.048 (11)* | |
H1B | −0.446 (8) | 0.623 (3) | 0.206 (6) | 0.048 (11)* | |
H1C | −0.497 (9) | 0.561 (3) | 0.084 (5) | 0.052 (13)* | |
H7A | 0.276 (7) | 0.413 (3) | 0.909 (5) | 0.049 (11)* | |
H7B | 0.464 (8) | 0.345 (3) | 0.886 (5) | 0.045 (11)* | |
H7C | 0.207 (10) | 0.331 (3) | 0.846 (6) | 0.067 (14)* | |
H15 | 0.453 (9) | 0.277 (3) | 0.182 (6) | 0.064 (15)* | |
H20 | 0.836 (9) | 0.239 (3) | 0.749 (6) | 0.077 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N7 | 0.0319 (16) | 0.0392 (19) | 0.0424 (16) | 0.0078 (16) | 0.0029 (13) | 0.0062 (15) |
C3 | 0.0330 (17) | 0.0359 (19) | 0.0359 (18) | 0.0052 (15) | 0.0113 (14) | 0.0048 (14) |
C4 | 0.0312 (16) | 0.038 (2) | 0.0321 (15) | 0.0014 (15) | 0.0071 (12) | 0.0001 (15) |
C5 | 0.0272 (16) | 0.035 (2) | 0.0375 (17) | 0.0035 (14) | 0.0060 (13) | −0.0028 (14) |
C6 | 0.0317 (18) | 0.048 (2) | 0.0344 (19) | 0.0053 (16) | 0.0066 (14) | −0.0003 (15) |
N1 | 0.0424 (18) | 0.0363 (18) | 0.0265 (14) | 0.0061 (15) | 0.0086 (13) | 0.0006 (14) |
C1A | 0.033 (2) | 0.048 (3) | 0.032 (2) | −0.006 (2) | 0.0141 (18) | −0.006 (2) |
O1A | 0.038 (2) | 0.084 (4) | 0.070 (3) | −0.018 (2) | 0.0154 (18) | −0.045 (3) |
O2A | 0.034 (2) | 0.064 (4) | 0.043 (2) | −0.0026 (18) | 0.0142 (16) | −0.017 (2) |
C2 | 0.0297 (17) | 0.0290 (18) | 0.0290 (16) | 0.0002 (14) | 0.0063 (13) | −0.0025 (13) |
C1B | 0.032 (7) | 0.062 (8) | 0.041 (7) | −0.003 (6) | 0.008 (6) | −0.021 (7) |
O1B | 0.037 (7) | 0.085 (11) | 0.049 (8) | 0.006 (8) | 0.002 (6) | −0.034 (7) |
O2B | 0.025 (7) | 0.066 (11) | 0.035 (8) | −0.013 (7) | 0.014 (6) | −0.003 (8) |
O11 | 0.0372 (13) | 0.0517 (16) | 0.0208 (10) | 0.0112 (11) | 0.0018 (9) | −0.0040 (10) |
O12 | 0.0262 (12) | 0.0686 (19) | 0.0368 (13) | 0.0042 (13) | 0.0064 (9) | −0.0096 (12) |
C13 | 0.0265 (15) | 0.0255 (17) | 0.0221 (14) | −0.0032 (13) | 0.0057 (12) | −0.0001 (12) |
C14 | 0.0255 (15) | 0.0301 (18) | 0.0228 (14) | 0.0005 (13) | 0.0005 (12) | −0.0035 (12) |
O15 | 0.0407 (14) | 0.0349 (13) | 0.0329 (12) | 0.0100 (11) | 0.0096 (10) | −0.0047 (10) |
C16 | 0.0390 (18) | 0.0307 (19) | 0.0232 (14) | 0.0034 (14) | 0.0023 (13) | −0.0010 (13) |
O17 | 0.0730 (19) | 0.0342 (14) | 0.0352 (14) | −0.0064 (13) | 0.0012 (12) | −0.0073 (11) |
C18 | 0.0349 (17) | 0.0302 (17) | 0.0234 (14) | 0.0011 (14) | 0.0041 (13) | 0.0051 (13) |
O19 | 0.0506 (15) | 0.0603 (17) | 0.0333 (13) | −0.0233 (13) | 0.0117 (11) | 0.0021 (12) |
O20 | 0.0426 (13) | 0.0478 (16) | 0.0199 (10) | −0.0120 (12) | 0.0043 (9) | −0.0027 (10) |
Geometric parameters (Å, º) top
N7—C6 | 1.474 (4) | C1A—O2A | 1.235 (4) |
N7—H7A | 1.01 (4) | C1A—C2 | 1.531 (5) |
N7—H7B | 0.84 (5) | C2—C1B | 1.539 (9) |
N7—H7C | 0.91 (6) | C2—H2 | 0.9800 |
C3—C4 | 1.524 (5) | C1B—O1B | 1.233 (5) |
C3—C2 | 1.526 (4) | C1B—O2B | 1.235 (5) |
C3—H3A | 0.9700 | O11—C13 | 1.264 (4) |
C3—H3B | 0.9700 | O12—C13 | 1.229 (4) |
C4—C5 | 1.506 (4) | C13—C14 | 1.541 (4) |
C4—H4A | 0.9700 | C14—O15 | 1.406 (4) |
C4—H4B | 0.9700 | C14—C16 | 1.531 (4) |
C5—C6 | 1.509 (5) | C14—H14 | 0.9800 |
C5—H5A | 0.9700 | O15—H15 | 0.87 (5) |
C5—H5B | 0.9700 | C16—O17 | 1.416 (4) |
C6—H6A | 0.9700 | C16—C18 | 1.523 (4) |
C6—H6B | 0.9700 | C16—H16 | 0.9800 |
N1—C2 | 1.484 (4) | O17—H17 | 0.8200 |
N1—H1A | 0.89 (4) | C18—O19 | 1.218 (4) |
N1—H1B | 0.91 (4) | C18—O20 | 1.296 (4) |
N1—H1C | 0.86 (5) | O20—H20 | 0.96 (5) |
C1A—O1A | 1.229 (4) | | |
| | | |
C6—N7—H7A | 111 (2) | O1A—C1A—O2A | 124.9 (4) |
C6—N7—H7B | 117 (3) | O1A—C1A—C2 | 117.5 (3) |
H7A—N7—H7B | 110 (4) | O2A—C1A—C2 | 117.1 (3) |
C6—N7—H7C | 115 (3) | N1—C2—C3 | 109.3 (2) |
H7A—N7—H7C | 100 (4) | N1—C2—C1A | 111.5 (3) |
H7B—N7—H7C | 101 (4) | C3—C2—C1A | 107.8 (3) |
C4—C3—C2 | 113.6 (2) | N1—C2—C1B | 103.7 (7) |
C4—C3—H3A | 108.8 | C3—C2—C1B | 123.1 (14) |
C2—C3—H3A | 108.8 | N1—C2—H2 | 109.4 |
C4—C3—H3B | 108.8 | C3—C2—H2 | 109.4 |
C2—C3—H3B | 108.8 | C1A—C2—H2 | 109.4 |
H3A—C3—H3B | 107.7 | C1B—C2—H2 | 101.1 |
C5—C4—C3 | 111.1 (2) | O1B—C1B—O2B | 124.3 (10) |
C5—C4—H4A | 109.4 | O1B—C1B—C2 | 117.1 (8) |
C3—C4—H4A | 109.4 | O2B—C1B—C2 | 115.9 (8) |
C5—C4—H4B | 109.4 | O12—C13—O11 | 124.8 (3) |
C3—C4—H4B | 109.4 | O12—C13—C14 | 117.8 (3) |
H4A—C4—H4B | 108.0 | O11—C13—C14 | 117.4 (2) |
C4—C5—C6 | 112.8 (3) | O15—C14—C16 | 111.7 (2) |
C4—C5—H5A | 109.0 | O15—C14—C13 | 114.3 (2) |
C6—C5—H5A | 109.0 | C16—C14—C13 | 108.5 (2) |
C4—C5—H5B | 109.0 | O15—C14—H14 | 107.3 |
C6—C5—H5B | 109.0 | C16—C14—H14 | 107.3 |
H5A—C5—H5B | 107.8 | C13—C14—H14 | 107.3 |
N7—C6—C5 | 110.5 (3) | C14—O15—H15 | 112 (3) |
N7—C6—H6A | 109.6 | O17—C16—C18 | 109.0 (3) |
C5—C6—H6A | 109.6 | O17—C16—C14 | 109.1 (2) |
N7—C6—H6B | 109.6 | C18—C16—C14 | 110.5 (3) |
C5—C6—H6B | 109.6 | O17—C16—H16 | 109.4 |
H6A—C6—H6B | 108.1 | C18—C16—H16 | 109.4 |
C2—N1—H1A | 109 (2) | C14—C16—H16 | 109.4 |
C2—N1—H1B | 112 (3) | C16—O17—H17 | 109.5 |
H1A—N1—H1B | 113 (4) | O19—C18—O20 | 124.2 (3) |
C2—N1—H1C | 110 (3) | O19—C18—C16 | 121.3 (3) |
H1A—N1—H1C | 109 (4) | O20—C18—C16 | 114.6 (3) |
H1B—N1—H1C | 104 (4) | C18—O20—H20 | 111 (3) |
| | | |
C2—C3—C4—C5 | 171.8 (3) | C3—C2—C1B—O2B | −85 (3) |
C3—C4—C5—C6 | −179.9 (3) | O12—C13—C14—O15 | 164.1 (3) |
C4—C5—C6—N7 | 171.4 (3) | O11—C13—C14—O15 | −16.4 (4) |
C4—C3—C2—N1 | −175.8 (3) | O12—C13—C14—C16 | −70.5 (4) |
C4—C3—C2—C1A | 62.9 (4) | O11—C13—C14—C16 | 109.0 (3) |
C4—C3—C2—C1B | 62.3 (8) | O15—C14—C16—O17 | 66.2 (3) |
O1A—C1A—C2—N1 | −34.1 (6) | C13—C14—C16—O17 | −60.7 (3) |
O2A—C1A—C2—N1 | 153.2 (5) | O15—C14—C16—C18 | −53.6 (3) |
O1A—C1A—C2—C3 | 85.8 (6) | C13—C14—C16—C18 | 179.5 (2) |
O2A—C1A—C2—C3 | −86.8 (5) | O17—C16—C18—O19 | −4.4 (4) |
N1—C2—C1B—O1B | −11 (3) | C14—C16—C18—O19 | 115.4 (4) |
C3—C2—C1B—O1B | 113 (2) | O17—C16—C18—O20 | 174.1 (3) |
N1—C2—C1B—O2B | 151 (2) | C14—C16—C18—O20 | −66.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O12i | 0.89 (4) | 2.22 (4) | 2.959 (4) | 141 (3) |
N1—H1A···O17ii | 0.89 (4) | 2.38 (4) | 3.001 (4) | 127 (3) |
N1—H1B···O19iii | 0.91 (4) | 1.99 (4) | 2.890 (4) | 169 (4) |
N1—H1C···O2Aiv | 0.86 (5) | 2.00 (5) | 2.849 (6) | 169 (4) |
N7—H7A···O2Av | 1.01 (4) | 1.67 (5) | 2.675 (5) | 174 (4) |
N7—H7B···O11v | 0.84 (5) | 2.08 (5) | 2.870 (4) | 156 (4) |
N7—H7C···O12vi | 0.91 (6) | 2.38 (5) | 3.095 (4) | 135 (4) |
O15—H15···O12iv | 0.87 (5) | 1.95 (5) | 2.808 (4) | 170 (5) |
O17—H17···O2Avii | 0.82 | 2.47 | 3.230 (7) | 155 |
O20—H20···O11v | 0.96 (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) x−1, y, z; (v) x, y, z+1; (vi) x−1, y, z+1; (vii) −x+1, y−1/2, −z. |
(V)
L-lysine
L-hydrogen tartrate
top
Crystal data top
C6H15N2O2+·C4H5O6− | F(000) = 316 |
Mr = 296.28 | Dx = 1.478 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 1401 reflections |
a = 5.1022 (11) Å | θ = 2.3–24.0° |
b = 17.444 (4) Å | µ = 0.13 mm−1 |
c = 7.547 (2) Å | T = 298 K |
β = 97.748 (4)° | Plate, colourless |
V = 665.6 (3) Å3 | 0.35 × 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 tube | Rint = 0.028 |
Graphite monochromator | θmax = 25.0°, θmin = 2.3° |
ϕ and ω scan | h = −5→6 |
3396 measured reflections | k = −20→20 |
1200 independent reflections | l = −6→8 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H 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 parameters | Δρmax = 0.25 e Å−3 |
303 restraints | Δρmin = −0.19 e Å−3 |
Crystal data top
C6H15N2O2+·C4H5O6− | V = 665.6 (3) Å3 |
Mr = 296.28 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 5.1022 (11) Å | µ = 0.13 mm−1 |
b = 17.444 (4) Å | T = 298 K |
c = 7.547 (2) Å | 0.35 × 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 reflections | Rint = 0.028 |
1200 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.048 | 303 restraints |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | Δρmax = 0.25 e Å−3 |
1200 reflections | Δρmin = −0.19 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1A | 0.060 (3) | 0.2889 (10) | −0.017 (2) | 0.058 (3) | 0.608 (6) |
O2A | −0.185 (2) | 0.3939 (7) | −0.0531 (15) | 0.055 (3) | 0.608 (6) |
N1A | −0.264 (3) | 0.2161 (5) | 0.1687 (15) | 0.044 (3) | 0.608 (6) |
HA1A | −0.0915 | 0.2054 | 0.1819 | 0.066* | 0.608 (6) |
HA1B | −0.3441 | 0.1921 | 0.0723 | 0.066* | 0.608 (6) |
HA1C | −0.3319 | 0.2004 | 0.2648 | 0.066* | 0.608 (6) |
N7A | 0.304 (4) | 0.4380 (10) | 0.8529 (13) | 0.055 (3) | 0.608 (6) |
HA7A | 0.2475 | 0.4862 | 0.8414 | 0.083* | 0.608 (6) |
HA7B | 0.4665 | 0.4371 | 0.9131 | 0.083* | 0.608 (6) |
HA7C | 0.1957 | 0.4110 | 0.9120 | 0.083* | 0.608 (6) |
C1A | −0.123 (2) | 0.3301 (6) | 0.0162 (13) | 0.043 (2) | 0.608 (6) |
C2A | −0.3021 (16) | 0.2996 (4) | 0.1470 (11) | 0.0406 (19) | 0.608 (6) |
H2A | −0.4858 | 0.3085 | 0.0944 | 0.049* | 0.608 (6) |
C3A | −0.2569 (14) | 0.3413 (4) | 0.3220 (10) | 0.0481 (16) | 0.608 (6) |
H3A1 | −0.3505 | 0.3141 | 0.4066 | 0.058* | 0.608 (6) |
H3A2 | −0.3354 | 0.3918 | 0.3051 | 0.058* | 0.608 (6) |
C4A | 0.0281 (16) | 0.3506 (7) | 0.4045 (12) | 0.057 (2) | 0.608 (6) |
H4A1 | 0.1121 | 0.3008 | 0.4205 | 0.068* | 0.608 (6) |
H4A2 | 0.1231 | 0.3808 | 0.3259 | 0.068* | 0.608 (6) |
C5A | 0.0372 (17) | 0.3901 (6) | 0.5825 (12) | 0.0594 (18) | 0.608 (6) |
H5A1 | −0.0542 | 0.4388 | 0.5648 | 0.071* | 0.608 (6) |
H5A2 | −0.0574 | 0.3591 | 0.6596 | 0.071* | 0.608 (6) |
C6A | 0.3080 (16) | 0.4041 (6) | 0.6737 (12) | 0.061 (2) | 0.608 (6) |
H6A1 | 0.3995 | 0.4385 | 0.6018 | 0.073* | 0.608 (6) |
H6A2 | 0.4045 | 0.3560 | 0.6855 | 0.073* | 0.608 (6) |
O1B | 0.102 (4) | 0.2779 (13) | 0.020 (3) | 0.053 (4) | 0.392 (6) |
O2B | −0.137 (4) | 0.3842 (9) | 0.004 (2) | 0.052 (3) | 0.392 (6) |
N1B | −0.315 (5) | 0.2029 (8) | 0.152 (2) | 0.041 (3) | 0.392 (6) |
HB1A | −0.1730 | 0.1794 | 0.1206 | 0.061* | 0.392 (6) |
HB1B | −0.4473 | 0.1998 | 0.0626 | 0.061* | 0.392 (6) |
HB1C | −0.3618 | 0.1803 | 0.2486 | 0.061* | 0.392 (6) |
N7B | 0.312 (6) | 0.4550 (15) | 0.8378 (16) | 0.048 (4) | 0.392 (6) |
HB7A | 0.1609 | 0.4437 | 0.8786 | 0.072* | 0.392 (6) |
HB7B | 0.3685 | 0.5008 | 0.8787 | 0.072* | 0.392 (6) |
HB7C | 0.4329 | 0.4197 | 0.8750 | 0.072* | 0.392 (6) |
C1B | −0.093 (4) | 0.3156 (10) | 0.0480 (18) | 0.046 (3) | 0.392 (6) |
C2B | −0.252 (3) | 0.2843 (8) | 0.1919 (16) | 0.044 (2) | 0.392 (6) |
H2B | −0.4163 | 0.3135 | 0.1891 | 0.053* | 0.392 (6) |
C3B | −0.089 (2) | 0.2925 (6) | 0.3744 (15) | 0.055 (2) | 0.392 (6) |
H3B1 | −0.1891 | 0.2716 | 0.4638 | 0.066* | 0.392 (6) |
H3B2 | 0.0711 | 0.2625 | 0.3768 | 0.066* | 0.392 (6) |
C4B | −0.015 (3) | 0.3741 (7) | 0.424 (2) | 0.062 (3) | 0.392 (6) |
H4B1 | 0.0317 | 0.4006 | 0.3194 | 0.074* | 0.392 (6) |
H4B2 | −0.1665 | 0.4001 | 0.4614 | 0.074* | 0.392 (6) |
C5B | 0.210 (3) | 0.3772 (7) | 0.569 (2) | 0.069 (2) | 0.392 (6) |
H5B1 | 0.3661 | 0.3569 | 0.5255 | 0.083* | 0.392 (6) |
H5B2 | 0.1712 | 0.3446 | 0.6667 | 0.083* | 0.392 (6) |
C6B | 0.268 (3) | 0.4564 (7) | 0.6396 (17) | 0.060 (2) | 0.392 (6) |
H6B1 | 0.4248 | 0.4760 | 0.5949 | 0.072* | 0.392 (6) |
H6B2 | 0.1213 | 0.4900 | 0.5985 | 0.072* | 0.392 (6) |
O11 | 0.3544 (5) | 0.0759 (2) | 1.1095 (3) | 0.0403 (7) | |
O12 | −0.0654 (5) | 0.0868 (2) | 0.9926 (3) | 0.0376 (6) | |
C13 | 0.1708 (7) | 0.0760 (2) | 0.9791 (4) | 0.0294 (8) | |
C14 | 0.2475 (7) | 0.0643 (2) | 0.7912 (5) | 0.0320 (9) | |
H14 | 0.1139 | 0.0309 | 0.7255 | 0.038* | |
O15 | 0.4948 (6) | 0.02965 (18) | 0.7877 (4) | 0.0363 (7) | |
H15 | 0.610 (9) | 0.057 (3) | 0.847 (6) | 0.035 (12)* | |
C16 | 0.2275 (8) | 0.1430 (3) | 0.6977 (5) | 0.0382 (10) | |
H16 | 0.0417 | 0.1590 | 0.6782 | 0.046* | |
O17 | 0.3761 (8) | 0.1986 (2) | 0.8029 (4) | 0.0540 (9) | |
H17 | 0.285 (14) | 0.232 (5) | 0.860 (10) | 0.10 (2)* | |
C18 | 0.3290 (9) | 0.1367 (3) | 0.5176 (5) | 0.0430 (11) | |
O19 | 0.5278 (9) | 0.1689 (3) | 0.4848 (5) | 0.0711 (12) | |
O20 | 0.1809 (6) | 0.0936 (3) | 0.4058 (4) | 0.0610 (11) | |
H20 | 0.250 (16) | 0.085 (6) | 0.304 (11) | 0.13 (3)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.045 (6) | 0.053 (5) | 0.083 (7) | 0.017 (4) | 0.033 (6) | 0.005 (4) |
O2A | 0.054 (5) | 0.045 (4) | 0.068 (6) | 0.009 (3) | 0.018 (4) | 0.020 (3) |
N1A | 0.053 (7) | 0.036 (5) | 0.047 (4) | −0.015 (4) | 0.022 (4) | −0.014 (3) |
N7A | 0.059 (5) | 0.045 (7) | 0.066 (5) | −0.028 (5) | 0.027 (5) | −0.026 (5) |
C1A | 0.036 (4) | 0.027 (5) | 0.067 (4) | −0.003 (4) | 0.012 (4) | −0.005 (4) |
C2A | 0.035 (4) | 0.028 (4) | 0.062 (4) | −0.004 (3) | 0.019 (3) | −0.003 (3) |
C3A | 0.050 (3) | 0.037 (3) | 0.060 (4) | −0.002 (3) | 0.019 (3) | −0.018 (3) |
C4A | 0.056 (4) | 0.051 (4) | 0.066 (4) | 0.000 (3) | 0.012 (3) | −0.016 (3) |
C5A | 0.056 (4) | 0.054 (4) | 0.070 (4) | −0.004 (3) | 0.017 (3) | −0.018 (3) |
C6A | 0.057 (4) | 0.057 (4) | 0.072 (4) | −0.016 (4) | 0.022 (3) | −0.023 (4) |
O1B | 0.035 (7) | 0.050 (8) | 0.078 (9) | 0.004 (5) | 0.027 (7) | 0.000 (6) |
O2B | 0.047 (7) | 0.034 (6) | 0.081 (9) | 0.004 (5) | 0.024 (7) | 0.005 (6) |
N1B | 0.036 (7) | 0.034 (6) | 0.055 (7) | −0.021 (5) | 0.020 (5) | −0.011 (5) |
N7B | 0.044 (7) | 0.042 (10) | 0.066 (6) | −0.012 (6) | 0.038 (5) | −0.010 (5) |
C1B | 0.039 (5) | 0.030 (5) | 0.073 (5) | −0.005 (4) | 0.023 (4) | −0.004 (4) |
C2B | 0.038 (4) | 0.033 (5) | 0.066 (5) | −0.002 (4) | 0.024 (4) | −0.009 (4) |
C3B | 0.050 (4) | 0.044 (4) | 0.069 (4) | −0.001 (4) | 0.004 (4) | −0.020 (4) |
C4B | 0.059 (4) | 0.048 (5) | 0.077 (4) | 0.005 (4) | 0.003 (4) | −0.020 (4) |
C5B | 0.065 (5) | 0.059 (5) | 0.080 (5) | −0.001 (4) | −0.002 (4) | −0.025 (4) |
C6B | 0.062 (5) | 0.047 (5) | 0.070 (5) | 0.000 (5) | 0.004 (4) | −0.018 (5) |
O11 | 0.0308 (13) | 0.0699 (19) | 0.0204 (12) | 0.0069 (15) | 0.0037 (10) | −0.0024 (14) |
O12 | 0.0247 (13) | 0.0583 (18) | 0.0311 (13) | 0.0024 (13) | 0.0085 (10) | −0.0027 (13) |
C13 | 0.0296 (19) | 0.034 (2) | 0.0248 (18) | 0.0015 (16) | 0.0057 (14) | −0.0003 (17) |
C14 | 0.0254 (18) | 0.047 (2) | 0.0236 (18) | 0.0006 (16) | 0.0042 (14) | −0.0098 (16) |
O15 | 0.0333 (15) | 0.0463 (16) | 0.0310 (14) | 0.0035 (13) | 0.0101 (11) | −0.0085 (13) |
C16 | 0.035 (2) | 0.058 (3) | 0.0229 (19) | 0.0136 (19) | 0.0084 (15) | 0.0042 (18) |
O17 | 0.079 (2) | 0.0457 (19) | 0.0383 (17) | 0.0004 (18) | 0.0130 (16) | −0.0044 (14) |
C18 | 0.040 (2) | 0.067 (3) | 0.0231 (19) | 0.011 (2) | 0.0074 (17) | 0.005 (2) |
O19 | 0.078 (3) | 0.099 (3) | 0.043 (2) | −0.017 (2) | 0.0317 (18) | −0.0054 (18) |
O20 | 0.0477 (18) | 0.112 (3) | 0.0252 (16) | −0.005 (2) | 0.0126 (14) | −0.0116 (18) |
Geometric parameters (Å, º) top
O1A—C1A | 1.230 (8) | N7B—HB7A | 0.8900 |
O2A—C1A | 1.252 (10) | N7B—HB7B | 0.8900 |
N1A—C2A | 1.477 (10) | N7B—HB7C | 0.8900 |
N1A—HA1A | 0.8900 | C1B—C2B | 1.540 (10) |
N1A—HA1B | 0.8900 | C2B—C3B | 1.515 (12) |
N1A—HA1C | 0.8900 | C2B—H2B | 0.9800 |
N7A—C6A | 1.479 (11) | C3B—C4B | 1.505 (12) |
N7A—HA7A | 0.8900 | C3B—H3B1 | 0.9700 |
N7A—HA7B | 0.8900 | C3B—H3B2 | 0.9700 |
N7A—HA7C | 0.8900 | C4B—C5B | 1.481 (12) |
C1A—C2A | 1.529 (9) | C4B—H4B1 | 0.9700 |
C2A—C3A | 1.497 (9) | C4B—H4B2 | 0.9700 |
C2A—H2A | 0.9800 | C5B—C6B | 1.495 (12) |
C3A—C4A | 1.511 (10) | C5B—H5B1 | 0.9700 |
C3A—H3A1 | 0.9700 | C5B—H5B2 | 0.9700 |
C3A—H3A2 | 0.9700 | C6B—H6B1 | 0.9700 |
C4A—C5A | 1.505 (10) | C6B—H6B2 | 0.9700 |
C4A—H4A1 | 0.9700 | O11—C13 | 1.264 (4) |
C4A—H4A2 | 0.9700 | O12—C13 | 1.237 (4) |
C5A—C6A | 1.478 (11) | C13—C14 | 1.535 (5) |
C5A—H5A1 | 0.9700 | C14—O15 | 1.402 (4) |
C5A—H5A2 | 0.9700 | C14—C16 | 1.540 (6) |
C6A—H6A1 | 0.9700 | C14—H14 | 0.9800 |
C6A—H6A2 | 0.9700 | O15—H15 | 0.84 (5) |
O1B—C1B | 1.233 (10) | C16—O17 | 1.408 (6) |
O2B—C1B | 1.255 (11) | C16—C18 | 1.522 (5) |
N1B—C2B | 1.479 (10) | C16—H16 | 0.9800 |
N1B—HB1A | 0.8900 | O17—H17 | 0.89 (8) |
N1B—HB1B | 0.8900 | C18—O19 | 1.214 (6) |
N1B—HB1C | 0.8900 | C18—O20 | 1.295 (6) |
N7B—C6B | 1.483 (12) | O20—H20 | 0.90 (9) |
| | | |
O1A—C1A—O2A | 126.2 (7) | C3B—C2B—C1B | 109.4 (7) |
O1A—C1A—C2A | 117.7 (7) | N1B—C2B—H2B | 109.4 |
O2A—C1A—C2A | 116.0 (6) | C3B—C2B—H2B | 109.4 |
N1A—C2A—C3A | 112.3 (7) | C1B—C2B—H2B | 109.4 |
N1A—C2A—C1A | 109.4 (6) | C4B—C3B—C2B | 113.7 (9) |
C3A—C2A—C1A | 111.5 (5) | C4B—C3B—H3B1 | 108.8 |
N1A—C2A—H2A | 107.8 | C2B—C3B—H3B1 | 108.8 |
C3A—C2A—H2A | 107.8 | C4B—C3B—H3B2 | 108.8 |
C1A—C2A—H2A | 107.8 | C2B—C3B—H3B2 | 108.8 |
C2A—C3A—C4A | 116.1 (6) | H3B1—C3B—H3B2 | 107.7 |
C2A—C3A—H3A1 | 108.3 | C5B—C4B—C3B | 111.2 (9) |
C4A—C3A—H3A1 | 108.3 | C5B—C4B—H4B1 | 109.4 |
C2A—C3A—H3A2 | 108.3 | C3B—C4B—H4B1 | 109.4 |
C4A—C3A—H3A2 | 108.3 | C5B—C4B—H4B2 | 109.4 |
H3A1—C3A—H3A2 | 107.4 | C3B—C4B—H4B2 | 109.4 |
C5A—C4A—C3A | 109.2 (7) | H4B1—C4B—H4B2 | 108.0 |
C5A—C4A—H4A1 | 109.8 | C4B—C5B—C6B | 113.3 (9) |
C3A—C4A—H4A1 | 109.8 | C4B—C5B—H5B1 | 108.9 |
C5A—C4A—H4A2 | 109.8 | C6B—C5B—H5B1 | 108.9 |
C3A—C4A—H4A2 | 109.8 | C4B—C5B—H5B2 | 108.9 |
H4A1—C4A—H4A2 | 108.3 | C6B—C5B—H5B2 | 108.9 |
C6A—C5A—C4A | 113.9 (7) | H5B1—C5B—H5B2 | 107.7 |
C6A—C5A—H5A1 | 108.8 | N7B—C6B—C5B | 109.8 (11) |
C4A—C5A—H5A1 | 108.8 | N7B—C6B—H6B1 | 109.7 |
C6A—C5A—H5A2 | 108.8 | C5B—C6B—H6B1 | 109.7 |
C4A—C5A—H5A2 | 108.8 | N7B—C6B—H6B2 | 109.7 |
H5A1—C5A—H5A2 | 107.7 | C5B—C6B—H6B2 | 109.7 |
C5A—C6A—N7A | 111.4 (10) | H6B1—C6B—H6B2 | 108.2 |
C5A—C6A—H6A1 | 109.3 | O12—C13—O11 | 124.4 (3) |
N7A—C6A—H6A1 | 109.3 | O12—C13—C14 | 117.9 (3) |
C5A—C6A—H6A2 | 109.3 | O11—C13—C14 | 117.7 (3) |
N7A—C6A—H6A2 | 109.3 | O15—C14—C13 | 114.6 (3) |
H6A1—C6A—H6A2 | 108.0 | O15—C14—C16 | 112.3 (3) |
C2B—N1B—HB1A | 109.5 | C13—C14—C16 | 107.2 (3) |
C2B—N1B—HB1B | 109.5 | O15—C14—H14 | 107.4 |
HB1A—N1B—HB1B | 109.5 | C13—C14—H14 | 107.4 |
C2B—N1B—HB1C | 109.5 | C16—C14—H14 | 107.4 |
HB1A—N1B—HB1C | 109.5 | C14—O15—H15 | 108 (3) |
HB1B—N1B—HB1C | 109.5 | O17—C16—C18 | 109.3 (4) |
C6B—N7B—HB7A | 109.5 | O17—C16—C14 | 111.0 (3) |
C6B—N7B—HB7B | 109.5 | C18—C16—C14 | 109.6 (3) |
HB7A—N7B—HB7B | 109.5 | O17—C16—H16 | 109.0 |
C6B—N7B—HB7C | 109.5 | C18—C16—H16 | 109.0 |
HB7A—N7B—HB7C | 109.5 | C14—C16—H16 | 109.0 |
HB7B—N7B—HB7C | 109.5 | C16—O17—H17 | 116 (5) |
O1B—C1B—O2B | 125.8 (9) | O19—C18—O20 | 124.5 (4) |
O1B—C1B—C2B | 116.5 (9) | O19—C18—C16 | 122.9 (4) |
O2B—C1B—C2B | 115.4 (8) | O20—C18—C16 | 112.6 (4) |
N1B—C2B—C3B | 110.7 (10) | C18—O20—H20 | 113 (6) |
N1B—C2B—C1B | 108.5 (7) | | |
| | | |
O1A—C1A—C2A—N1A | −16.2 (15) | C2B—C3B—C4B—C5B | −161.1 (14) |
O2A—C1A—C2A—N1A | 160.7 (10) | C3B—C4B—C5B—C6B | −172.4 (15) |
O1A—C1A—C2A—C3A | 108.6 (13) | C4B—C5B—C6B—N7B | 135 (2) |
O2A—C1A—C2A—C3A | −74.5 (11) | O12—C13—C14—O15 | −161.2 (4) |
N1A—C2A—C3A—C4A | 75.2 (10) | O11—C13—C14—O15 | 20.6 (5) |
C1A—C2A—C3A—C4A | −47.9 (10) | O12—C13—C14—C16 | 73.4 (4) |
C2A—C3A—C4A—C5A | −177.4 (8) | O11—C13—C14—C16 | −104.9 (4) |
C3A—C4A—C5A—C6A | −178.6 (9) | O15—C14—C16—O17 | −73.5 (4) |
C4A—C5A—C6A—N7A | −176.0 (11) | C13—C14—C16—O17 | 53.3 (4) |
O1B—C1B—C2B—N1B | −51 (2) | O15—C14—C16—C18 | 47.3 (4) |
O2B—C1B—C2B—N1B | 144.9 (17) | C13—C14—C16—C18 | 174.1 (3) |
O1B—C1B—C2B—C3B | 70 (2) | O17—C16—C18—O19 | 8.2 (6) |
O2B—C1B—C2B—C3B | −94.2 (16) | C14—C16—C18—O19 | −113.7 (5) |
N1B—C2B—C3B—C4B | 179.5 (15) | O17—C16—C18—O20 | −172.0 (4) |
C1B—C2B—C3B—C4B | 60.0 (16) | C14—C16—C18—O20 | 66.2 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—HA1B···O12i | 0.89 | 2.45 | 2.870 (11) | 110 |
N1A—HA1B···O17ii | 0.89 | 2.32 | 3.119 (13) | 149 |
N1A—HA1C···O19iii | 0.89 | 1.97 | 2.862 (13) | 177 |
N7A—HA7A···O12iv | 0.89 | 2.41 | 3.16 (2) | 141 |
N7A—HA7B···O2Av | 0.89 | 1.92 | 2.72 (3) | 149 |
N7A—HA7C···O1Avi | 0.89 | 2.32 | 3.10 (2) | 145 |
N7A—HA7C···O2Avi | 0.89 | 2.02 | 2.79 (2) | 145 |
O15—H15···O12vii | 0.84 (5) | 1.93 (5) | 2.736 (4) | 160 (4) |
O17—H17···O1Avi | 0.89 (8) | 1.86 (8) | 2.742 (12) | 172 (7) |
O20—H20···O11i | 0.90 (9) | 1.63 (9) | 2.533 (4) | 175 (9) |
N1B—HB1A···O12i | 0.89 | 2.00 | 2.753 (19) | 142 |
N1B—HB1B···O17ii | 0.89 | 2.04 | 2.884 (19) | 157 |
N1B—HB1C···O19iii | 0.89 | 1.95 | 2.80 (2) | 160 |
N7B—HB7A···O2Bvi | 0.89 | 2.16 | 3.02 (3) | 162 |
N7B—HB7B···O11viii | 0.89 | 1.92 | 2.71 (2) | 146 |
N7B—HB7C···O2Bv | 0.89 | 2.36 | 3.17 (4) | 151 |
O17—H17···O1Bvi | 0.89 (8) | 1.82 (8) | 2.678 (18) | 164 (7) |
Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z−1; (iii) x−1, 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 formula | C6H15N4O2+·C4H5O6− | 2(C6H15N4O2)+·C4H4O62− | 2(C6H15N4O2)+·C4H4O62−·H2O | C6H15N2O2+·C4H5O6− |
Mr | 324.30 | 498.51 | 460.49 | 296.28 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21 | Monoclinic, P21/c | Monoclinic, P21 |
Temperature (K) | 298 | 298 | 298 | 2983 |
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), 90 | 90, 90.820 (7), 90 | 90, 96.366 (4), 90 |
V (Å3) | 714.3 (4) | 1149.9 (4) | 2184.2 (13) | 658.7 (2) |
Z | 2 | 2 | 4 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.13 | 0.12 | 0.12 | 0.13 |
Crystal size (mm) | 0.25 × 0.2 × 0.1 | 0.42 × 0.27 × 0.15 | 0.47 × 0.10 × 0.07 | 0.4 × 0.35 × 0.2 |
|
Data collection |
Diffractometer | Bruker 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 |
Rint | 0.057 | 0.016 | 0.046 | 0.025 |
(sin θ/λ)max (Å−1) | 0.595 | 0.595 | 0.595 | 0.617 |
|
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 reflections | 2508 | 2162 | 3842 | 1342 |
No. of parameters | 260 | 380 | 379 | 242 |
No. of restraints | 52 | 2 | 72 | 79 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.23 | 0.37, −0.17 | 0.75, −0.30 | 0.15, −0.16 |
| (V) |
Crystal data |
Chemical formula | C6H15N2O2+·C4H5O6− |
Mr | 296.28 |
Crystal system, space group | Monoclinic, 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 |
V (Å3) | 665.6 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.35 × 0.25 × 0.20 |
|
Data collection |
Diffractometer | Bruker SMART CCD area detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3396, 1200, 1146 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.116, 1.13 |
No. of reflections | 1200 |
No. of parameters | 288 |
No. of restraints | 303 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.25, −0.19 |
Hydrogen-bond geometry (Å, º) for (I) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 1.06 (5) | 1.74 (5) | 2.788 (4) | 169 (3) |
N1—H1B···O17 | 0.82 (4) | 2.21 (4) | 3.001 (4) | 160 (3) |
N1—H1C···O1ii | 1.04 (6) | 2.29 (6) | 3.171 (4) | 141 (4) |
N1—H1C···O2ii | 1.04 (6) | 2.31 (6) | 3.300 (4) | 159 (4) |
N6—H6···O19 | 0.84 (4) | 2.11 (4) | 2.892 (4) | 155 (4) |
N8—H8A···O2iii | 0.96 (4) | 1.91 (4) | 2.807 (4) | 155 (3) |
N8—H8B···O11iv | 0.92 (4) | 1.89 (4) | 2.801 (4) | 174 (4) |
N9—H9A···O12iv | 0.85 (4) | 2.25 (4) | 3.099 (4) | 176 (3) |
N9—H9B···O19 | 0.89 (4) | 2.34 (4) | 3.111 (5) | 145 (3) |
N9—H9B···O20v | 0.89 (4) | 2.33 (4) | 2.976 (4) | 129 (3) |
O12—H12···O12vi | 1.225 | 1.225 | 2.451 (4) | 180 |
O15—H15···O1i | 0.91 (5) | 2.02 (5) | 2.813 (3) | 144 (4) |
O17—H17···O20vii | 0.82 | 2.13 | 2.953 (4) | 178 |
O20—H20···O20v | 1.233 | 1.233 | 2.466 (4) | 180 |
Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x−1, −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) x−1, y, z. |
Hydrogen-bond geometry (Å, º) for (II) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O21 | 0.89 (4) | 2.01 (4) | 2.892 (3) | 171 (3) |
N1—H1B···O11 | 0.94 (3) | 1.82 (4) | 2.759 (3) | 177 (3) |
N1—H1C···O22i | 0.91 (3) | 1.86 (3) | 2.770 (3) | 176 (3) |
N6—H6···O27i | 0.90 (3) | 1.91 (3) | 2.785 (3) | 164 (3) |
N8—H8A···O12ii | 0.82 (4) | 2.16 (4) | 2.961 (4) | 167 (4) |
N8—H8B···O21iii | 0.84 (3) | 2.15 (3) | 2.934 (3) | 155 (3) |
N9—H9A···O29i | 0.86 (4) | 2.30 (4) | 3.130 (4) | 162 (3) |
N9—H9B···O21iii | 0.88 (4) | 2.33 (4) | 3.127 (4) | 151 (3) |
N11—H11A···O1 | 0.84 (4) | 2.22 (4) | 3.046 (3) | 166 (4) |
N11—H11B···O30iv | 0.93 (3) | 1.81 (3) | 2.732 (3) | 170 (3) |
N11—H11C···O29 | 0.92 (5) | 1.99 (5) | 2.906 (4) | 176 (3) |
N16—H16···O2v | 0.89 (3) | 1.92 (3) | 2.781 (3) | 162 (3) |
N18—H18A···O1vi | 0.89 (3) | 2.00 (4) | 2.863 (3) | 165 (3) |
N18—H18B···O29vii | 0.99 (4) | 1.86 (4) | 2.840 (3) | 168 (3) |
N19—H19A···O2v | 0.90 (4) | 2.03 (4) | 2.841 (4) | 149 (3) |
N19—H19B···O29vii | 0.90 (5) | 2.52 (5) | 3.224 (4) | 136 (4) |
O25—H25···O1 | 0.83 | 2.23 | 2.840 (3) | 131 |
O27—H27···O11 | 0.86 (5) | 1.89 (5) | 2.698 (4) | 155 (4) |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) x−1, y, z; (iii) −x, y+1/2, −z+1; (iv) −x+2, y+1/2, −z+2; (v) −x+2, y−1/2, −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···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O30i | 0.99 (5) | 1.90 (5) | 2.879 (4) | 168 (4) |
N1—H1B···O11ii | 1.02 (5) | 2.00 (5) | 2.938 (5) | 151 (4) |
N1—H1C···O2iii | 1.06 (5) | 1.75 (5) | 2.794 (4) | 165 (4) |
N7—H7A···O12iv | 0.96 (6) | 1.90 (6) | 2.852 (5) | 169 (5) |
N7—H7B···O21 | 1.02 (6) | 1.77 (6) | 2.774 (4) | 169 (5) |
N7—H7C···O1W | 0.90 (4) | 2.06 (4) | 2.950 (9) | 172 (4) |
N7—H7C···O2W | 0.90 (4) | 2.30 (4) | 2.956 (9) | 130 (3) |
N11—H11A···O1v | 0.87 (5) | 2.36 (5) | 3.146 (5) | 149 (3) |
N11—H11A···O2vi | 0.87 (5) | 2.44 (4) | 3.061 (4) | 129 (3) |
N11—H11B···O21 | 0.84 (5) | 2.09 (6) | 2.868 (4) | 155 (5) |
N11—H11B···O25 | 0.84 (5) | 2.31 (5) | 2.929 (4) | 131 (4) |
N11—H11C···O12iii | 0.90 (5) | 1.98 (5) | 2.872 (5) | 174 (4) |
N17—H17A···O27vii | 0.85 (6) | 2.24 (5) | 2.926 (4) | 138 (4) |
N17—H17A···O29vii | 0.85 (6) | 2.25 (6) | 2.983 (5) | 144 (4) |
N17—H17B···O30viii | 0.98 (6) | 1.94 (6) | 2.915 (5) | 169 (4) |
N17—H17C···O2 | 0.78 (5) | 2.20 (5) | 2.972 (5) | 176 (4) |
O25—H25···O29ix | 0.88 (6) | 1.85 (6) | 2.708 (4) | 164 (5) |
O27—H27···O22x | 0.82 | 1.90 | 2.702 (4) | 167.0 |
O3W—O29···2.904 (1)xi | 3_756 | O3W | O1W | 3.030 (2) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, −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, z−1/2; (vi) x+1, y, z; (vii) x−1, 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···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O12i | 0.89 (4) | 2.22 (4) | 2.959 (4) | 141 (3) |
N1—H1A···O17ii | 0.89 (4) | 2.38 (4) | 3.001 (4) | 127 (3) |
N1—H1B···O19iii | 0.91 (4) | 1.99 (4) | 2.890 (4) | 169 (4) |
N1—H1C···O2Aiv | 0.86 (5) | 2.00 (5) | 2.849 (6) | 169 (4) |
N7—H7A···O2Av | 1.01 (4) | 1.67 (5) | 2.675 (5) | 174 (4) |
N7—H7B···O11v | 0.84 (5) | 2.08 (5) | 2.870 (4) | 156 (4) |
N7—H7C···O12vi | 0.91 (6) | 2.38 (5) | 3.095 (4) | 135 (4) |
O15—H15···O12iv | 0.87 (5) | 1.95 (5) | 2.808 (4) | 170 (5) |
O17—H17···O2Avii | 0.82 | 2.47 | 3.230 (7) | 154.8 |
O20—H20···O11v | 0.96 (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) x−1, y, z; (v) x, y, z+1; (vi) x−1, y, z+1; (vii) −x+1, y−1/2, −z. |
Hydrogen-bond geometry (Å, º) for (V) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—HA1B···O12i | 0.89 | 2.45 | 2.870 (11) | 109.5 |
N1A—HA1B···O17ii | 0.89 | 2.32 | 3.119 (13) | 148.6 |
N1A—HA1C···O19iii | 0.89 | 1.97 | 2.862 (13) | 177.3 |
N7A—HA7A···O12iv | 0.89 | 2.41 | 3.16 (2) | 141.2 |
N7A—HA7B···O2Av | 0.89 | 1.92 | 2.72 (3) | 149.1 |
N7A—HA7C···O1Avi | 0.89 | 2.32 | 3.10 (2) | 145.4 |
N7A—HA7C···O2Avi | 0.89 | 2.02 | 2.79 (2) | 144.8 |
O15—H15···O12vii | 0.84 (5) | 1.93 (5) | 2.736 (4) | 160 (4) |
O17—H17···O1Avi | 0.89 (8) | 1.86 (8) | 2.742 (12) | 172 (7) |
O20—H20···O11i | 0.90 (9) | 1.63 (9) | 2.533 (4) | 175 (9) |
N1B—HB1A···O12i | 0.89 | 2.00 | 2.753 (19) | 141.9 |
N1B—HB1B···O17ii | 0.89 | 2.04 | 2.884 (19) | 156.8 |
N1B—HB1C···O19iii | 0.89 | 1.95 | 2.80 (2) | 159.6 |
N7B—HB7A···O2Bvi | 0.89 | 2.16 | 3.02 (3) | 162.0 |
N7B—HB7B···O11viii | 0.89 | 1.92 | 2.71 (2) | 146.1 |
N7B—HB7C···O2Bv | 0.89 | 2.36 | 3.17 (4) | 151.4 |
O17—H17···O1Bvi | 0.89 (8) | 1.82 (8) | 2.678 (18) | 164 (7) |
Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z−1; (iii) x−1, 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. |