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The complexes of L-arginine and DL-lysine with pimelic acid are made up of singly positively charged zwitterionic amino acid cations and doubly negatively charged pimelate ions in a 2:1 ratio. In both structures, the amino acid molecules form twofold symmetric or centrosymmetric pairs that are stabilized by hydrogen bonds involving α-amino and α-carboxylate groups. In the L-arginine complex, these pairs form columns along the shortest cell dimension, stabilized by intermolecular hydrogen bonds involving α-amino and α-carboxylate groups. The columns are connected by hydrogen bonds and water bridges to give rise to an amino acid layer. Adjacent layers are then connected by pimelate ions. Unlike molecular ions aggregate into alternating distinct layers in the DL-lysine complex. In the amino acid layer, hydrogen-bonded lysinium dimers related by a glide plane are connected by hydrogen bonds involving α-amino and α-carboxylate groups into head-to-tail sequences. Interestingly, the aggregation pattern observed in L-arginine hemipimelate monohydrate is very similar to those in DL-arginine formate dihydrate, DL-arginine acetate monohydrate and L-arginine hemiglutarate monohydrate. Similarly, the aggregation of amino acid molecules is very similar in DL-lysine hemipimelate 0.53-hydrate, DL-lysine formate and DL-lysine hydrochloride. The complexes thus demonstrate how, in related structures, the effects of a change in composition, and sometimes even those of reversal in chirality, can be accommodated by minor adjustments in essentially the same aggregation pattern. It also transpires that the conformation of the argininium ion is the same in the four argininium complexes; the same is true about the conformation of the lysinium ion in the three lysinium complexes. This result indicates a relation between, and mutual dependence of, conformation and aggregation.
Supporting information
CCDC references: 223328; 223329
For both compounds, data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998). Data reduction: SAINT for dl-lysin. Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) for arg; SHELXS97 <Sheldrick, 1990> for dl-lysin. Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for arg; SHELXL97 <Sheldrick, 1997> for dl-lysin. For both compounds, molecular graphics: ORTEP-3 for Windows (Farrugia, 1997). Software used to prepare material for publication: MSWORD XP for arg; PLATON (Spek, 2003) for dl-lysin.
Crystal data top
C19H44N8O10 | F(000) = 1176 |
Mr = 544.62 | Dx = 1.333 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
a = 30.278 (7) Å | Cell parameters from 1100 reflections |
b = 5.1414 (12) Å | θ = 2.5–26.0° |
c = 19.355 (5) Å | µ = 0.11 mm−1 |
β = 115.776 (7)° | T = 293 K |
V = 2713.2 (12) Å3 | Plate, colourless |
Z = 4 | 0.42 × 0.07 × 0.06 mm |
Data collection top
CCD area detector diffractometer | 2863 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 26.4°, θmin = 1.2° |
ω–2/q scans | h = −37→37 |
14507 measured reflections | k = −6→6 |
3097 independent reflections | l = −23→23 |
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)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.094 | Calculated w = 1/[σ2(Fo2) + (0.0414P)2 + 0.6691P] where P = (Fo2 + 2Fc2)/3 |
S = 1.23 | (Δ/σ)max < 0.001 |
3097 reflections | Δρmax = 0.19 e Å−3 |
359 parameters | Δρmin = −0.16 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −10 (10) |
Crystal data top
C19H44N8O10 | V = 2713.2 (12) Å3 |
Mr = 544.62 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 30.278 (7) Å | µ = 0.11 mm−1 |
b = 5.1414 (12) Å | T = 293 K |
c = 19.355 (5) Å | 0.42 × 0.07 × 0.06 mm |
β = 115.776 (7)° | |
Data collection top
CCD area detector diffractometer | 2863 reflections with I > 2σ(I) |
14507 measured reflections | Rint = 0.025 |
3097 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.094 | Δρmax = 0.19 e Å−3 |
S = 1.23 | Δρmin = −0.16 e Å−3 |
3097 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
359 parameters | Absolute structure parameter: −10 (10) |
1 restraint | |
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 | |
N1 | 0.67246 (6) | 0.5154 (4) | 0.67869 (10) | 0.0307 (4) | |
H1B | 0.6432 | 0.5817 | 0.6693 | 0.046* | |
H1A | 0.6899 | 0.6330 | 0.6674 | 0.046* | |
H1C | 0.6882 | 0.4726 | 0.7281 | 0.046* | |
O1 | 0.75045 (5) | 0.3121 (4) | 0.66065 (10) | 0.0403 (4) | |
O2 | 0.71651 (7) | −0.0800 (4) | 0.63744 (11) | 0.0423 (4) | |
C1 | 0.71555 (8) | 0.1593 (5) | 0.64535 (13) | 0.0289 (5) | |
C2 | 0.66586 (7) | 0.2793 (5) | 0.63062 (12) | 0.0293 (5) | |
H2 | 0.6464 | 0.1510 | 0.6428 | 0.035* | |
C3 | 0.63792 (8) | 0.3610 (5) | 0.54654 (13) | 0.0354 (6) | |
H3A | 0.6071 | 0.4396 | 0.5395 | 0.042* | |
H3B | 0.6569 | 0.4932 | 0.5357 | 0.042* | |
C4 | 0.62701 (9) | 0.1422 (5) | 0.48853 (13) | 0.0357 (6) | |
H4A | 0.6576 | 0.0621 | 0.4949 | 0.043* | |
H4B | 0.6073 | 0.0106 | 0.4980 | 0.043* | |
C5 | 0.59988 (9) | 0.2409 (6) | 0.40709 (13) | 0.0383 (6) | |
H5A | 0.5892 | 0.0947 | 0.3719 | 0.046* | |
H5B | 0.5710 | 0.3368 | 0.4019 | 0.046* | |
N6 | 0.63148 (7) | 0.4091 (5) | 0.38769 (11) | 0.0389 (5) | |
H6 | 0.6626 | 0.3920 | 0.4140 | 0.047* | |
C7 | 0.61596 (8) | 0.5859 (6) | 0.33285 (13) | 0.0365 (6) | |
N8 | 0.56886 (7) | 0.6419 (5) | 0.29363 (11) | 0.0400 (5) | |
H8A | 0.5598 | 0.7608 | 0.2589 | 0.048* | |
H8B | 0.5473 | 0.5594 | 0.3028 | 0.048* | |
N9 | 0.64803 (8) | 0.7170 (6) | 0.31702 (14) | 0.0563 (7) | |
H9A | 0.6381 | 0.8350 | 0.2821 | 0.068* | |
H9B | 0.6788 | 0.6842 | 0.3417 | 0.068* | |
N11 | 0.80462 (7) | 0.5444 (4) | 0.80221 (10) | 0.0316 (4) | |
H11B | 0.8330 | 0.6138 | 0.8081 | 0.047* | |
H11A | 0.7879 | 0.6603 | 0.8156 | 0.047* | |
H11C | 0.7872 | 0.4996 | 0.7533 | 0.047* | |
O11 | 0.73012 (6) | 0.3320 (4) | 0.82595 (10) | 0.0404 (4) | |
O12 | 0.76753 (7) | −0.0507 (4) | 0.85604 (11) | 0.0445 (5) | |
C11 | 0.76612 (8) | 0.1854 (5) | 0.84259 (13) | 0.0300 (5) | |
C12 | 0.81424 (8) | 0.3108 (5) | 0.85139 (13) | 0.0301 (5) | |
H12 | 0.8326 | 0.1844 | 0.8362 | 0.036* | |
C13 | 0.84568 (9) | 0.3926 (5) | 0.93459 (13) | 0.0377 (6) | |
H13A | 0.8740 | 0.4873 | 0.9368 | 0.045* | |
H13B | 0.8267 | 0.5112 | 0.9501 | 0.045* | |
C14 | 0.86368 (9) | 0.1705 (6) | 0.99222 (13) | 0.0386 (6) | |
H14A | 0.8806 | 0.0434 | 0.9753 | 0.046* | |
H14B | 0.8358 | 0.0854 | 0.9946 | 0.046* | |
C15 | 0.89824 (9) | 0.2678 (6) | 1.07171 (14) | 0.0433 (6) | |
H15A | 0.9121 | 0.1206 | 1.1057 | 0.052* | |
H15B | 0.9250 | 0.3637 | 1.0688 | 0.052* | |
N16 | 0.87247 (7) | 0.4350 (5) | 1.10263 (11) | 0.0428 (6) | |
H16 | 0.8410 | 0.4290 | 1.0819 | 0.051* | |
C17 | 0.89471 (8) | 0.5954 (6) | 1.16071 (13) | 0.0388 (6) | |
N18 | 0.94234 (7) | 0.6326 (5) | 1.19129 (12) | 0.0482 (6) | |
H18A | 0.9600 | 0.5512 | 1.1735 | 0.058* | |
H18B | 0.9559 | 0.7384 | 1.2291 | 0.058* | |
N19 | 0.86868 (7) | 0.7287 (6) | 1.18907 (13) | 0.0553 (7) | |
H19A | 0.8831 | 0.8355 | 1.2264 | 0.066* | |
H19B | 0.8374 | 0.7081 | 1.1701 | 0.066* | |
O21 | 0.58452 (6) | 0.5899 (5) | 0.68366 (11) | 0.0548 (6) | |
O22 | 0.51710 (6) | 0.4846 (5) | 0.69392 (11) | 0.0569 (6) | |
C23 | 0.53977 (8) | 0.6177 (6) | 0.66600 (14) | 0.0385 (6) | |
C24 | 0.51014 (9) | 0.8179 (6) | 0.60773 (15) | 0.0445 (7) | |
H24A | 0.4977 | 0.9411 | 0.6329 | 0.053* | |
H24B | 0.4820 | 0.7308 | 0.5684 | 0.053* | |
C25 | 0.53524 (9) | 0.9697 (6) | 0.56855 (14) | 0.0417 (6) | |
H25A | 0.5530 | 0.8498 | 0.5512 | 0.050* | |
H25B | 0.5589 | 1.0865 | 0.6055 | 0.050* | |
C26 | 0.5000 | 1.1287 (8) | 0.5000 | 0.0431 (9) | |
H26 | 0.4811 (10) | 1.244 (6) | 0.5186 (15) | 0.054 (9)* | |
O31 | 0.96786 (6) | 0.5437 (5) | 0.82208 (11) | 0.0531 (5) | |
O32 | 0.88975 (7) | 0.5902 (5) | 0.79374 (12) | 0.0650 (7) | |
C33 | 0.93436 (9) | 0.6476 (6) | 0.83169 (14) | 0.0403 (6) | |
C34 | 0.94373 (10) | 0.8557 (7) | 0.89182 (17) | 0.0538 (8) | |
H34A | 0.9207 | 0.9961 | 0.8680 | 0.065* | |
H34B | 0.9360 | 0.7824 | 0.9314 | 0.065* | |
C35 | 0.99355 (9) | 0.9710 (6) | 0.92998 (14) | 0.0459 (7) | |
H35A | 0.9992 | 1.0798 | 0.8936 | 0.055* | |
H35B | 1.0178 | 0.8329 | 0.9460 | 0.055* | |
C36 | 1.0000 | 1.1344 (9) | 1.0000 | 0.0457 (9) | |
H36 | 1.0289 (9) | 1.248 (6) | 1.0138 (15) | 0.046 (8)* | |
OW1 | 0.73285 (8) | 0.8261 (5) | 0.96017 (15) | 0.0533 (6) | |
HW1A | 0.7399 (10) | 0.834 (7) | 0.9226 (16) | 0.050 (9)* | |
HW1B | 0.7412 (14) | 0.692 (9) | 0.978 (2) | 0.069 (14)* | |
OW2 | 0.76206 (8) | 0.7984 (6) | 0.54240 (15) | 0.0525 (5) | |
HW2A | 0.7514 (11) | 0.807 (7) | 0.5782 (17) | 0.058 (9)* | |
HW2B | 0.7563 (14) | 0.666 (9) | 0.528 (2) | 0.062 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0251 (9) | 0.0363 (12) | 0.0335 (10) | 0.0049 (9) | 0.0154 (8) | 0.0024 (9) |
O1 | 0.0255 (8) | 0.0429 (11) | 0.0552 (10) | −0.0048 (8) | 0.0201 (7) | −0.0138 (9) |
O2 | 0.0446 (10) | 0.0298 (10) | 0.0611 (12) | 0.0042 (8) | 0.0309 (9) | 0.0026 (9) |
C1 | 0.0274 (11) | 0.0344 (14) | 0.0270 (11) | 0.0027 (10) | 0.0138 (9) | 0.0019 (10) |
C2 | 0.0244 (10) | 0.0306 (12) | 0.0353 (11) | −0.0004 (10) | 0.0153 (9) | 0.0001 (10) |
C3 | 0.0300 (11) | 0.0350 (14) | 0.0390 (12) | 0.0028 (10) | 0.0130 (10) | 0.0042 (11) |
C4 | 0.0335 (12) | 0.0363 (14) | 0.0373 (12) | −0.0038 (11) | 0.0153 (10) | 0.0017 (11) |
C5 | 0.0340 (12) | 0.0451 (16) | 0.0348 (12) | −0.0083 (11) | 0.0140 (10) | −0.0016 (12) |
N6 | 0.0243 (9) | 0.0520 (14) | 0.0388 (11) | −0.0013 (10) | 0.0122 (8) | 0.0075 (11) |
C7 | 0.0294 (11) | 0.0476 (16) | 0.0345 (12) | −0.0021 (12) | 0.0158 (10) | −0.0009 (12) |
N8 | 0.0265 (10) | 0.0515 (14) | 0.0415 (11) | −0.0008 (10) | 0.0143 (8) | 0.0077 (11) |
N9 | 0.0296 (11) | 0.0757 (19) | 0.0643 (14) | 0.0033 (12) | 0.0212 (10) | 0.0320 (15) |
N11 | 0.0293 (9) | 0.0341 (11) | 0.0350 (10) | −0.0045 (9) | 0.0174 (8) | −0.0033 (9) |
O11 | 0.0283 (8) | 0.0461 (11) | 0.0500 (10) | 0.0052 (8) | 0.0200 (7) | 0.0129 (9) |
O12 | 0.0536 (11) | 0.0299 (10) | 0.0616 (12) | −0.0040 (9) | 0.0359 (10) | −0.0018 (9) |
C11 | 0.0305 (12) | 0.0358 (14) | 0.0275 (11) | −0.0040 (11) | 0.0162 (9) | −0.0033 (10) |
C12 | 0.0276 (11) | 0.0291 (12) | 0.0375 (12) | 0.0006 (10) | 0.0178 (9) | −0.0010 (11) |
C13 | 0.0331 (12) | 0.0386 (15) | 0.0396 (13) | −0.0050 (11) | 0.0142 (10) | −0.0044 (12) |
C14 | 0.0382 (12) | 0.0409 (15) | 0.0370 (13) | 0.0068 (12) | 0.0165 (10) | −0.0028 (12) |
C15 | 0.0350 (12) | 0.0543 (17) | 0.0385 (13) | 0.0117 (13) | 0.0140 (11) | −0.0010 (13) |
N16 | 0.0248 (9) | 0.0625 (16) | 0.0396 (11) | 0.0006 (11) | 0.0125 (9) | −0.0121 (12) |
C17 | 0.0270 (11) | 0.0532 (17) | 0.0363 (12) | 0.0021 (12) | 0.0139 (10) | −0.0031 (12) |
N18 | 0.0287 (10) | 0.0685 (17) | 0.0475 (12) | −0.0012 (11) | 0.0165 (9) | −0.0192 (13) |
N19 | 0.0271 (10) | 0.079 (2) | 0.0607 (14) | −0.0043 (12) | 0.0198 (10) | −0.0292 (15) |
O21 | 0.0297 (9) | 0.0762 (16) | 0.0649 (12) | 0.0154 (10) | 0.0264 (8) | 0.0195 (12) |
O22 | 0.0349 (9) | 0.0723 (16) | 0.0699 (13) | 0.0145 (10) | 0.0289 (9) | 0.0298 (12) |
C23 | 0.0298 (12) | 0.0487 (16) | 0.0395 (13) | 0.0054 (12) | 0.0173 (10) | 0.0004 (12) |
C24 | 0.0312 (12) | 0.0550 (18) | 0.0511 (15) | 0.0067 (13) | 0.0214 (11) | 0.0083 (14) |
C25 | 0.0332 (13) | 0.0486 (16) | 0.0414 (14) | −0.0042 (12) | 0.0145 (11) | −0.0008 (13) |
C26 | 0.044 (2) | 0.040 (2) | 0.050 (2) | 0.000 | 0.0243 (18) | 0.000 |
O31 | 0.0360 (9) | 0.0624 (13) | 0.0664 (12) | −0.0083 (10) | 0.0274 (9) | −0.0155 (12) |
O32 | 0.0381 (10) | 0.0900 (18) | 0.0764 (13) | −0.0204 (12) | 0.0338 (10) | −0.0377 (14) |
C33 | 0.0360 (13) | 0.0484 (16) | 0.0419 (13) | −0.0097 (12) | 0.0219 (11) | −0.0047 (13) |
C34 | 0.0369 (13) | 0.066 (2) | 0.0612 (17) | −0.0055 (14) | 0.0236 (13) | −0.0141 (17) |
C35 | 0.0409 (14) | 0.0511 (17) | 0.0451 (14) | −0.0073 (13) | 0.0182 (12) | 0.0009 (14) |
C36 | 0.046 (2) | 0.041 (2) | 0.045 (2) | 0.000 | 0.0140 (18) | 0.000 |
OW1 | 0.0506 (12) | 0.0610 (16) | 0.0600 (14) | 0.0068 (12) | 0.0349 (11) | 0.0084 (13) |
OW2 | 0.0487 (12) | 0.0552 (16) | 0.0634 (14) | −0.0062 (11) | 0.0335 (11) | −0.0063 (13) |
Geometric parameters (Å, º) top
N1—C2 | 1.489 (3) | C14—C15 | 1.521 (3) |
O1—C1 | 1.244 (3) | C15—N16 | 1.453 (3) |
O2—C1 | 1.242 (3) | N16—C17 | 1.319 (3) |
C1—C2 | 1.534 (3) | C17—N18 | 1.313 (3) |
C2—C3 | 1.531 (3) | C17—N19 | 1.330 (3) |
C3—C4 | 1.521 (4) | O21—C23 | 1.253 (3) |
C4—C5 | 1.513 (3) | O22—C23 | 1.246 (3) |
C5—N6 | 1.455 (3) | C23—C24 | 1.502 (4) |
N6—C7 | 1.319 (3) | C24—C25 | 1.504 (4) |
C7—N8 | 1.323 (3) | C25—C26 | 1.528 (3) |
C7—N9 | 1.323 (3) | C26—C25i | 1.528 (3) |
N11—C12 | 1.481 (3) | O31—C33 | 1.230 (3) |
O11—C11 | 1.247 (3) | O32—C33 | 1.260 (3) |
O12—C11 | 1.239 (3) | C33—C34 | 1.514 (4) |
C11—C12 | 1.533 (3) | C34—C35 | 1.484 (4) |
C12—C13 | 1.531 (3) | C35—C36 | 1.533 (4) |
C13—C14 | 1.522 (4) | C36—C35ii | 1.533 (4) |
| | | |
O2—C1—O1 | 126.3 (2) | C14—C13—C12 | 115.2 (2) |
O2—C1—C2 | 116.7 (2) | C13—C14—C15 | 111.4 (2) |
O1—C1—C2 | 117.0 (2) | N16—C15—C14 | 110.77 (19) |
N1—C2—C3 | 107.62 (19) | C17—N16—C15 | 123.7 (2) |
N1—C2—C1 | 110.93 (18) | N18—C17—N16 | 121.9 (2) |
C3—C2—C1 | 110.60 (18) | N18—C17—N19 | 118.1 (2) |
C4—C3—C2 | 115.1 (2) | N16—C17—N19 | 120.0 (2) |
C5—C4—C3 | 111.5 (2) | O22—C23—O21 | 123.6 (3) |
N6—C5—C4 | 110.37 (19) | O22—C23—C24 | 116.1 (2) |
C7—N6—C5 | 124.97 (19) | O21—C23—C24 | 120.3 (2) |
N8—C7—N9 | 118.2 (2) | C23—C24—C25 | 117.8 (2) |
N8—C7—N6 | 122.0 (2) | C24—C25—C26 | 113.59 (19) |
N9—C7—N6 | 119.8 (2) | C25i—C26—C25 | 115.3 (4) |
O12—C11—O11 | 126.4 (2) | O31—C33—O32 | 123.7 (3) |
O12—C11—C12 | 116.4 (2) | O31—C33—C34 | 122.1 (2) |
O11—C11—C12 | 117.1 (2) | O32—C33—C34 | 114.1 (2) |
N11—C12—C13 | 108.18 (19) | C35—C34—C33 | 118.4 (2) |
N11—C12—C11 | 110.97 (18) | C34—C35—C36 | 111.7 (2) |
C13—C12—C11 | 111.02 (18) | C35ii—C36—C35 | 113.5 (4) |
Symmetry codes: (i) −x+1, y, −z+1; (ii) −x+2, y, −z+2. |
Crystal data top
0.5(C7H10O4)·(C6H15N2O2)·0.2(C2H6O)·0.53(H2O) | F(000) = 1050 |
Mr = 242.48 | Dx = 1.044 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 950 reflections |
a = 32.811 (17) Å | θ = 2.0–26.4° |
b = 11.012 (6) Å | µ = 0.08 mm−1 |
c = 8.552 (4) Å | T = 293 K |
β = 91.333 (9)° | Plate, colourless |
V = 3089 (3) Å3 | 0.72 × 0.21 × 0.04 mm |
Z = 8 | |
Data collection top
CCD area detector diffractometer | 2244 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 26.4°, θmin = 2.0° |
ω–2/q scans | h = −40→40 |
12142 measured reflections | k = −13→13 |
3160 independent reflections | l = −10→10 |
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)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.232 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | w = 1/[σ2(Fo2) + (0.1281P)2 + 2.548P] where P = (Fo2 + 2Fc2)/3 |
3160 reflections | (Δ/σ)max < 0.001 |
190 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
Crystal data top
0.5(C7H10O4)·(C6H15N2O2)·0.2(C2H6O)·0.53(H2O) | V = 3089 (3) Å3 |
Mr = 242.48 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 32.811 (17) Å | µ = 0.08 mm−1 |
b = 11.012 (6) Å | T = 293 K |
c = 8.552 (4) Å | 0.72 × 0.21 × 0.04 mm |
β = 91.333 (9)° | |
Data collection top
CCD area detector diffractometer | 2244 reflections with I > 2σ(I) |
12142 measured reflections | Rint = 0.035 |
3160 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.069 | 0 restraints |
wR(F2) = 0.232 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | Δρmax = 0.49 e Å−3 |
3160 reflections | Δρmin = −0.25 e Å−3 |
190 parameters | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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) |
O11 | 0.11065 (7) | 0.2546 (3) | 0.0930 (3) | 0.0696 (10) | |
O12 | 0.14038 (6) | 0.0760 (2) | 0.0910 (2) | 0.0493 (7) | |
C13 | 0.10957 (8) | 0.1414 (3) | 0.1057 (3) | 0.0461 (10) | |
C14A | 0.0740 (5) | 0.0850 (13) | 0.1768 (19) | 0.069 (4) | 0.572 |
C15 | 0.03647 (10) | 0.1519 (4) | 0.2015 (5) | 0.0754 (15) | |
C16 | 0.00000 | 0.0837 (6) | 0.25000 | 0.097 (3) | |
C14B | 0.0680 (6) | 0.076 (2) | 0.122 (3) | 0.091 (7) | 0.428 |
O1 | 0.26174 (5) | 0.38740 (16) | 0.9151 (2) | 0.0336 (6) | |
O2 | 0.23276 (5) | 0.52576 (16) | 0.7595 (2) | 0.0359 (6) | |
N1 | 0.19004 (6) | 0.32790 (18) | 1.0436 (2) | 0.0278 (6) | |
N7 | 0.18818 (6) | 0.03582 (19) | 0.3625 (2) | 0.0318 (7) | |
C1 | 0.23149 (7) | 0.4368 (2) | 0.8520 (3) | 0.0258 (7) | |
C2 | 0.18953 (7) | 0.3820 (2) | 0.8839 (3) | 0.0257 (7) | |
C3 | 0.17919 (8) | 0.2819 (2) | 0.7659 (3) | 0.0314 (8) | |
C4 | 0.17215 (8) | 0.3273 (2) | 0.5991 (3) | 0.0355 (8) | |
C5 | 0.16148 (8) | 0.2228 (3) | 0.4857 (3) | 0.0369 (8) | |
C6 | 0.19882 (8) | 0.1502 (2) | 0.4454 (3) | 0.0337 (8) | |
O19 | 0.0762 (10) | 0.4859 (17) | 0.075 (5) | 0.175 (15) | 0.200 |
O20 | 0.0998 (3) | 0.4638 (9) | 0.2544 (18) | 0.136 (5) | 0.400 |
C17 | 0.0607 (8) | 0.529 (3) | 0.214 (7) | 0.17 (2) | 0.200 |
C18 | 0.0570 (7) | 0.667 (3) | 0.200 (5) | 0.120 (15) | 0.200 |
O21 | 0.0532 (17) | 0.604 (6) | 0.109 (7) | 0.19 (2)* | 0.130 |
H14B | 0.06684 | 0.01490 | 0.11308 | 0.0824* | 0.572 |
H15A | 0.04218 | 0.21335 | 0.28022 | 0.0906* | |
H14A | 0.08302 | 0.05404 | 0.27799 | 0.0824* | 0.572 |
H16A | 0.00825 | 0.03133 | 0.33626 | 0.1166* | 0.500 |
H16B | −0.00825 | 0.03133 | 0.16374 | 0.1166* | 0.500 |
H15B | 0.02945 | 0.19407 | 0.10503 | 0.0906* | |
H14C | 0.07217 | 0.00152 | 0.18123 | 0.1090* | 0.428 |
H14D | 0.05766 | 0.05347 | 0.01869 | 0.1090* | 0.428 |
H1A | 0.20889 | 0.26987 | 1.04969 | 0.0417* | |
H1B | 0.16569 | 0.29621 | 1.06263 | 0.0417* | |
H1C | 0.19583 | 0.38529 | 1.11397 | 0.0417* | |
H2 | 0.16874 | 0.44575 | 0.87711 | 0.0308* | |
H3A | 0.15484 | 0.24006 | 0.79905 | 0.0377* | |
H3B | 0.20128 | 0.22330 | 0.76663 | 0.0377* | |
H4A | 0.15009 | 0.38599 | 0.59742 | 0.0426* | |
H4B | 0.19654 | 0.36803 | 0.56445 | 0.0426* | |
H5A | 0.14921 | 0.25591 | 0.39059 | 0.0443* | |
H5B | 0.14169 | 0.16970 | 0.53316 | 0.0443* | |
H6A | 0.21408 | 0.13111 | 0.54071 | 0.0404* | |
H6B | 0.21616 | 0.19896 | 0.37983 | 0.0404* | |
H7A | 0.21090 | −0.00426 | 0.34051 | 0.0476* | |
H7B | 0.17274 | −0.00994 | 0.42317 | 0.0476* | |
H7C | 0.17453 | 0.05302 | 0.27412 | 0.0476* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O11 | 0.0432 (13) | 0.0646 (17) | 0.102 (2) | −0.0002 (12) | 0.0232 (13) | 0.0081 (15) |
O12 | 0.0320 (10) | 0.0746 (15) | 0.0416 (12) | 0.0098 (10) | 0.0074 (8) | −0.0076 (10) |
C13 | 0.0272 (14) | 0.066 (2) | 0.0456 (17) | −0.0004 (13) | 0.0101 (11) | −0.0019 (15) |
C14A | 0.044 (6) | 0.054 (6) | 0.110 (9) | −0.008 (4) | 0.022 (5) | −0.012 (7) |
C15 | 0.0377 (18) | 0.089 (3) | 0.101 (3) | 0.0021 (18) | 0.0326 (19) | 0.002 (2) |
C16 | 0.040 (3) | 0.087 (4) | 0.167 (7) | 0.0000 | 0.046 (4) | 0.0000 |
C14B | 0.024 (6) | 0.099 (10) | 0.151 (18) | −0.033 (6) | 0.045 (9) | −0.079 (12) |
O1 | 0.0261 (9) | 0.0361 (10) | 0.0386 (10) | 0.0028 (7) | 0.0030 (7) | 0.0076 (8) |
O2 | 0.0363 (10) | 0.0349 (10) | 0.0366 (10) | −0.0031 (8) | 0.0030 (8) | 0.0121 (8) |
N1 | 0.0281 (10) | 0.0298 (11) | 0.0257 (11) | −0.0033 (8) | 0.0057 (8) | −0.0012 (8) |
N7 | 0.0344 (11) | 0.0338 (12) | 0.0273 (11) | −0.0012 (9) | 0.0055 (8) | −0.0020 (9) |
C1 | 0.0304 (12) | 0.0242 (12) | 0.0231 (11) | 0.0007 (10) | 0.0053 (9) | −0.0023 (9) |
C2 | 0.0279 (12) | 0.0254 (12) | 0.0238 (12) | 0.0018 (9) | 0.0031 (9) | −0.0004 (9) |
C3 | 0.0387 (14) | 0.0284 (13) | 0.0273 (13) | −0.0055 (10) | 0.0032 (10) | −0.0018 (10) |
C4 | 0.0464 (15) | 0.0307 (14) | 0.0294 (14) | 0.0046 (11) | −0.0021 (11) | −0.0020 (11) |
C5 | 0.0419 (15) | 0.0386 (15) | 0.0300 (13) | 0.0066 (12) | −0.0057 (11) | −0.0065 (11) |
C6 | 0.0377 (14) | 0.0334 (14) | 0.0300 (13) | −0.0016 (11) | 0.0023 (10) | −0.0060 (11) |
O19 | 0.18 (2) | 0.049 (11) | 0.30 (4) | 0.004 (13) | 0.06 (3) | 0.009 (17) |
O20 | 0.122 (8) | 0.093 (7) | 0.193 (12) | −0.044 (6) | 0.018 (8) | −0.021 (8) |
C17 | 0.060 (15) | 0.070 (18) | 0.37 (6) | 0.006 (13) | 0.10 (3) | −0.01 (3) |
C18 | 0.048 (12) | 0.094 (19) | 0.22 (4) | −0.018 (12) | 0.028 (16) | −0.05 (2) |
Geometric parameters (Å, º) top
O11—C13 | 1.252 (5) | C14B—H14D | 0.9712 |
O12—C13 | 1.250 (4) | C14B—H14C | 0.9720 |
O1—C1 | 1.244 (3) | C15—H15A | 0.9697 |
O2—C1 | 1.260 (3) | C15—H15B | 0.9698 |
O19—C17 | 1.39 (7) | C16—H16B | 0.9699 |
O19—O20 | 1.72 (4) | C16—H16A | 0.9699 |
O20—C17 | 1.50 (3) | C1—C2 | 1.533 (3) |
N1—C2 | 1.490 (3) | C2—C3 | 1.527 (3) |
N7—C6 | 1.483 (3) | C3—C4 | 1.524 (4) |
N1—H1B | 0.8903 | C4—C5 | 1.540 (4) |
N1—H1C | 0.8901 | C5—C6 | 1.510 (4) |
N1—H1A | 0.8900 | C2—H2 | 0.9796 |
N7—H7B | 0.8899 | C3—H3A | 0.9703 |
N7—H7C | 0.8899 | C3—H3B | 0.9703 |
N7—H7A | 0.8902 | C4—H4B | 0.9698 |
C13—C14B | 1.55 (2) | C4—H4A | 0.9702 |
C13—C14A | 1.466 (16) | C5—H5A | 0.9702 |
C14A—C15 | 1.455 (16) | C5—H5B | 0.9698 |
C14B—C15 | 1.50 (2) | C6—H6A | 0.9697 |
C15—C16 | 1.480 (5) | C6—H6B | 0.9702 |
C14A—H14A | 0.9699 | C17—C18 | 1.53 (5) |
C14A—H14B | 0.9706 | | |
| | | |
O1···O12i | 3.238 (3) | C1···H6Bi | 3.0454 |
O1···N1ii | 2.868 (3) | C1···H7Ai | 2.6420 |
O1···N1 | 2.700 (3) | C3···H6A | 2.8070 |
O1···C6iii | 3.377 (3) | C6···H3B | 2.8620 |
O1···C6i | 3.397 (4) | C13···H1Bv | 2.5424 |
O1···N7iii | 2.974 (3) | C13···H5A | 3.0117 |
O1···N7i | 3.038 (3) | C13···H7C | 2.7243 |
O2···N7i | 2.899 (3) | C13···H7Bvi | 2.9965 |
O2···N1iv | 2.802 (3) | H1A···H3B | 2.4814 |
O2···C4 | 3.238 (3) | H1A···O1 | 2.4698 |
O11···N1v | 2.769 (3) | H1A···O1ii | 2.0013 |
O11···O19 | 2.79 (2) | H1B···C13viii | 2.5424 |
O11···O20 | 2.713 (12) | H1B···O11viii | 1.8869 |
O12···N7 | 2.807 (3) | H1B···H3A | 2.3564 |
O12···O1i | 3.238 (3) | H1B···O12viii | 2.5765 |
O12···N1v | 3.247 (3) | H1C···O1 | 2.7822 |
O12···C6vi | 3.397 (4) | H1C···C1vii | 3.0398 |
O12···N7vi | 2.817 (3) | H1C···O2vii | 1.9765 |
O19···O11 | 2.79 (2) | H2···O20vii | 2.6645 |
O19···O20iv | 2.92 (4) | H2···H4A | 2.5418 |
O19···C17iv | 3.12 (7) | H3A···H1B | 2.3564 |
O20···O11 | 2.713 (12) | H3A···H5B | 2.4313 |
O20···O19vii | 2.92 (4) | H3B···H6A | 2.2311 |
O1···H1C | 2.7822 | H3B···H7Ax | 2.5115 |
O1···H7Ci | 2.7530 | H3B···C6 | 2.8620 |
O1···H1A | 2.4698 | H3B···H1A | 2.4814 |
O1···H1Aii | 2.0013 | H4A···O19vii | 2.8077 |
O1···H7Aiii | 2.5515 | H4A···H2 | 2.5418 |
O1···H7Biii | 2.7702 | H4A···O20vii | 2.7137 |
O1···H7Ai | 2.7077 | H4B···H6B | 2.5339 |
O1···H6Bi | 2.8066 | H4B···C1 | 2.7937 |
O1···H6Aiii | 2.8215 | H4B···O2 | 2.6682 |
O2···H4B | 2.6682 | H4B···C1iv | 3.0548 |
O2···H1Civ | 1.9765 | H5A···O11 | 2.8157 |
O2···H6Aiii | 2.6775 | H5A···C13 | 3.0117 |
O2···H7Ai | 2.0684 | H5A···H7C | 2.5909 |
O11···H15B | 2.7506 | H5B···O12x | 2.7510 |
O11···H15A | 2.8257 | H5B···H7B | 2.4250 |
O11···H1Bv | 1.8869 | H5B···H3A | 2.4313 |
O11···H5A | 2.8157 | H6A···O2ix | 2.6775 |
O12···H5Bvi | 2.7510 | H6A···O1ix | 2.8215 |
O12···H7C | 1.9210 | H6A···C1ix | 2.9212 |
O12···H1Bv | 2.5765 | H6A···H3B | 2.2311 |
O12···H7Bvi | 1.9461 | H6A···C3 | 2.8070 |
O19···H4Aiv | 2.8077 | H6B···H4B | 2.5339 |
O20···H4Aiv | 2.7137 | H6B···O1i | 2.8066 |
O20···H2iv | 2.6645 | H6B···C1i | 3.0454 |
N1···O1 | 2.700 (3) | H7A···O1i | 2.7077 |
N1···O11viii | 2.769 (3) | H7A···O2i | 2.0684 |
N1···O2vii | 2.802 (3) | H7A···O1ix | 2.5515 |
N1···O12viii | 3.247 (3) | H7A···H3Bvi | 2.5115 |
N1···C13viii | 3.397 (4) | H7A···C1i | 2.6420 |
N1···O1ii | 2.868 (3) | H7B···C13x | 2.9965 |
N7···O1ix | 2.974 (3) | H7B···O1ix | 2.7702 |
N7···O12 | 2.807 (3) | H7B···H5B | 2.4250 |
N7···O12x | 2.817 (3) | H7B···O12x | 1.9461 |
N7···C1i | 3.260 (4) | H7C···H5A | 2.5909 |
N7···O1i | 3.038 (3) | H7C···O12 | 1.9210 |
N7···O2i | 2.899 (3) | H7C···C13 | 2.7243 |
C1···N7i | 3.260 (4) | H7C···O1i | 2.7530 |
C1···C6i | 3.590 (4) | H14C···H16A | 2.5285 |
C4···O2 | 3.238 (3) | H14C···H16A | 2.5285 |
C6···O1ix | 3.377 (3) | H14D···H16B | 2.5298 |
C6···C1i | 3.590 (4) | H14D···H16B | 2.5298 |
C6···O12x | 3.397 (4) | H14D···H16Bxi | 2.4118 |
C6···O1i | 3.397 (4) | H14D···H16Avi | 2.4118 |
C13···N1v | 3.397 (4) | H15A···H15Bxii | 2.5766 |
C17···O19vii | 3.12 (7) | H15A···O11 | 2.8257 |
C1···H4Bvii | 3.0548 | H15B···O11 | 2.7506 |
C1···H6Aiii | 2.9212 | H15B···H15Axii | 2.5766 |
C1···H4B | 2.7937 | H16A···H14C | 2.5285 |
C1···H1Civ | 3.0398 | H16B···H14D | 2.5298 |
| | | |
H1A—N1—H1C | 109.46 | H16A—C16—H16B | 107.03 |
H1B—N1—H1C | 109.45 | C15xii—C16—H16B | 107.56 |
C2—N1—H1B | 109.47 | C15—C16—H16B | 107.56 |
C2—N1—H1C | 109.48 | C15xii—C16—H16A | 107.56 |
C2—N1—H1A | 109.50 | C15—C16—H16A | 107.56 |
H1A—N1—H1B | 109.46 | O1—C1—O2 | 125.1 (2) |
C6—N7—H7A | 109.46 | O1—C1—C2 | 117.5 (2) |
C6—N7—H7B | 109.45 | O2—C1—C2 | 117.4 (2) |
C6—N7—H7C | 109.48 | N1—C2—C1 | 109.24 (19) |
H7A—N7—H7B | 109.47 | N1—C2—C3 | 108.34 (18) |
H7A—N7—H7C | 109.48 | C1—C2—C3 | 110.7 (2) |
H7B—N7—H7C | 109.49 | C2—C3—C4 | 114.09 (19) |
O11—C13—C14A | 118.8 (6) | C3—C4—C5 | 111.8 (2) |
O11—C13—C14B | 119.8 (8) | C4—C5—C6 | 111.5 (2) |
O11—C13—O12 | 122.7 (3) | N7—C6—C5 | 112.1 (2) |
O12—C13—C14A | 116.8 (6) | N1—C2—H2 | 109.50 |
O12—C13—C14B | 117.1 (8) | C1—C2—H2 | 109.53 |
C13—C14A—C15 | 122.0 (10) | C3—C2—H2 | 109.53 |
C13—C14B—C15 | 113.4 (14) | C2—C3—H3A | 108.75 |
C14B—C15—C16 | 114.4 (9) | C2—C3—H3B | 108.74 |
C14A—C15—C16 | 118.4 (7) | C4—C3—H3A | 108.74 |
C15—C16—C15xii | 119.0 (5) | C4—C3—H3B | 108.73 |
C13—C14A—H14A | 106.83 | H3A—C3—H3B | 107.60 |
H14A—C14A—H14B | 106.63 | C3—C4—H4A | 109.22 |
C13—C14A—H14B | 106.77 | C3—C4—H4B | 109.24 |
C15—C14A—H14A | 106.87 | C5—C4—H4A | 109.26 |
C15—C14A—H14B | 106.84 | C5—C4—H4B | 109.29 |
H14C—C14B—H14D | 107.49 | H4A—C4—H4B | 107.94 |
C15—C14B—H14D | 108.88 | C4—C5—H5A | 109.33 |
C13—C14B—H14C | 108.97 | C4—C5—H5B | 109.37 |
C15—C14B—H14C | 108.86 | C6—C5—H5A | 109.32 |
C13—C14B—H14D | 109.03 | C6—C5—H5B | 109.34 |
C14A—C15—H15B | 107.70 | H5A—C5—H5B | 107.98 |
C16—C15—H15A | 107.69 | N7—C6—H6A | 109.20 |
C16—C15—H15B | 107.68 | N7—C6—H6B | 109.17 |
C14A—C15—H15A | 107.68 | C5—C6—H6A | 109.20 |
H15A—C15—H15B | 107.14 | C5—C6—H6B | 109.20 |
C14B—C15—H15B | 91.94 | H6A—C6—H6B | 107.91 |
C14B—C15—H15A | 125.28 | O19—C17—C18 | 108 (4) |
| | | |
O11—C13—C14A—C15 | 13.7 (15) | O2—C1—C2—C3 | 89.6 (3) |
O12—C13—C14A—C15 | 179.4 (9) | C1—C2—C3—C4 | −67.8 (3) |
C13—C14A—C15—C16 | 170.3 (8) | N1—C2—C3—C4 | 172.4 (2) |
C14A—C15—C16—C15xii | 170.9 (8) | C2—C3—C4—C5 | −179.5 (2) |
O1—C1—C2—N1 | 31.2 (3) | C3—C4—C5—C6 | −76.5 (3) |
O1—C1—C2—C3 | −88.0 (3) | C4—C5—C6—N7 | 168.7 (2) |
O2—C1—C2—N1 | −151.2 (2) | | |
Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x+1/2, −y+1/2, −z+2; (iii) −x+1/2, y+1/2, −z+3/2; (iv) x, −y+1, z−1/2; (v) x, y, z−1; (vi) x, −y, z−1/2; (vii) x, −y+1, z+1/2; (viii) x, y, z+1; (ix) −x+1/2, y−1/2, −z+3/2; (x) x, −y, z+1/2; (xi) −x, −y, −z; (xii) −x, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1ii | 0.8900 | 2.0013 | 2.868 (3) | 164.09 |
N1—H1B···O11viii | 0.8903 | 1.8869 | 2.769 (3) | 170.45 |
N1—H1B···O12viii | 0.8903 | 2.5765 | 3.247 (3) | 132.74 |
N1—H1C···O2vii | 0.8901 | 1.9765 | 2.802 (3) | 153.59 |
N7—H7A···O1ix | 0.8902 | 2.5515 | 2.974 (3) | 109.83 |
N7—H7A···O2i | 0.8902 | 2.0684 | 2.899 (3) | 154.82 |
N7—H7B···O12x | 0.8899 | 1.9461 | 2.817 (3) | 165.78 |
N7—H7C···O12 | 0.8899 | 1.9210 | 2.807 (3) | 173.15 |
Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x+1/2, −y+1/2, −z+2; (vii) x, −y+1, z+1/2; (viii) x, y, z+1; (ix) −x+1/2, y−1/2, −z+3/2; (x) x, −y, z+1/2. |
Experimental details
| (arg) | (dl-lysin) |
Crystal data |
Chemical formula | C19H44N8O10 | 0.5(C7H10O4)·(C6H15N2O2)·0.2(C2H6O)·0.53(H2O) |
Mr | 544.62 | 242.48 |
Crystal system, space group | Monoclinic, C2 | Monoclinic, C2/c |
Temperature (K) | 293 | 293 |
a, b, c (Å) | 30.278 (7), 5.1414 (12), 19.355 (5) | 32.811 (17), 11.012 (6), 8.552 (4) |
β (°) | 115.776 (7) | 91.333 (9) |
V (Å3) | 2713.2 (12) | 3089 (3) |
Z | 4 | 8 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.08 |
Crystal size (mm) | 0.42 × 0.07 × 0.06 | 0.72 × 0.21 × 0.04 |
|
Data collection |
Diffractometer | CCD area detector diffractometer | CCD area detector diffractometer |
Absorption correction | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14507, 3097, 2863 | 12142, 3160, 2244 |
Rint | 0.025 | 0.035 |
(sin θ/λ)max (Å−1) | 0.625 | 0.625 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.094, 1.23 | 0.069, 0.232, 1.12 |
No. of reflections | 3097 | 3160 |
No. of parameters | 359 | 190 |
No. of restraints | 1 | 0 |
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 |
Δρmax, Δρmin (e Å−3) | 0.19, −0.16 | 0.49, −0.25 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | ? |
Absolute structure parameter | −10 (10) | none |
Selected geometric parameters (Å, º) for (dl-lysin) topO11—C13 | 1.252 (5) | O19—O20 | 1.72 (4) |
O12—C13 | 1.250 (4) | O20—C17 | 1.50 (3) |
O1—C1 | 1.244 (3) | N1—C2 | 1.490 (3) |
O2—C1 | 1.260 (3) | N7—C6 | 1.483 (3) |
O19—C17 | 1.39 (7) | | |
| | | |
O11—C13—C14A | 118.8 (6) | O1—C1—C2 | 117.5 (2) |
O11—C13—C14B | 119.8 (8) | O2—C1—C2 | 117.4 (2) |
O11—C13—O12 | 122.7 (3) | N1—C2—C1 | 109.24 (19) |
O12—C13—C14A | 116.8 (6) | N1—C2—C3 | 108.34 (18) |
O12—C13—C14B | 117.1 (8) | N7—C6—C5 | 112.1 (2) |
O1—C1—O2 | 125.1 (2) | O19—C17—C18 | 108 (4) |
Hydrogen-bond geometry (Å, º) for (dl-lysin) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.8900 | 2.0013 | 2.868 (3) | 164.09 |
N1—H1B···O11ii | 0.8903 | 1.8869 | 2.769 (3) | 170.45 |
N1—H1B···O12ii | 0.8903 | 2.5765 | 3.247 (3) | 132.74 |
N1—H1C···O2iii | 0.8901 | 1.9765 | 2.802 (3) | 153.59 |
N7—H7A···O1iv | 0.8902 | 2.5515 | 2.974 (3) | 109.83 |
N7—H7A···O2v | 0.8902 | 2.0684 | 2.899 (3) | 154.82 |
N7—H7B···O12vi | 0.8899 | 1.9461 | 2.817 (3) | 165.78 |
N7—H7C···O12 | 0.8899 | 1.9210 | 2.807 (3) | 173.15 |
Symmetry codes: (i) −x+1/2, −y+1/2, −z+2; (ii) x, y, z+1; (iii) x, −y+1, z+1/2; (iv) −x+1/2, y−1/2, −z+3/2; (v) −x+1/2, −y+1/2, −z+1; (vi) x, −y, z+1/2. |
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