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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768103013685/de0021sup1.cif
Contains datablocks global, arg, dl-lysin

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103013685/de0021argsup2.hkl
Contains datablock arg

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768103013685/de0021dl-lysinsup3.hkl
Contains datablock lys

CCDC references: 223328; 223329

Computing details top

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.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
(arg) top
Crystal data top
C19H44N8O10F(000) = 1176
Mr = 544.62Dx = 1.333 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
a = 30.278 (7) ÅCell parameters from 1100 reflections
b = 5.1414 (12) Åθ = 2.5–26.0°
c = 19.355 (5) ŵ = 0.11 mm1
β = 115.776 (7)°T = 293 K
V = 2713.2 (12) Å3Plate, colourless
Z = 40.42 × 0.07 × 0.06 mm
Data collection top
CCD area detector
diffractometer
2863 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 26.4°, θmin = 1.2°
ω–2/q scansh = 3737
14507 measured reflectionsk = 66
3097 independent reflectionsl = 2323
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094Calculated w = 1/[σ2(Fo2) + (0.0414P)2 + 0.6691P]
where P = (Fo2 + 2Fc2)/3
S = 1.23(Δ/σ)max < 0.001
3097 reflectionsΔρmax = 0.19 e Å3
359 parametersΔρmin = 0.16 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 10 (10)
Crystal data top
C19H44N8O10V = 2713.2 (12) Å3
Mr = 544.62Z = 4
Monoclinic, C2Mo Kα radiation
a = 30.278 (7) ŵ = 0.11 mm1
b = 5.1414 (12) ÅT = 293 K
c = 19.355 (5) Å0.42 × 0.07 × 0.06 mm
β = 115.776 (7)°
Data collection top
CCD area detector
diffractometer
2863 reflections with I > 2σ(I)
14507 measured reflectionsRint = 0.025
3097 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094Δρmax = 0.19 e Å3
S = 1.23Δρmin = 0.16 e Å3
3097 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
359 parametersAbsolute 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
xyzUiso*/Ueq
N10.67246 (6)0.5154 (4)0.67869 (10)0.0307 (4)
H1B0.64320.58170.66930.046*
H1A0.68990.63300.66740.046*
H1C0.68820.47260.72810.046*
O10.75045 (5)0.3121 (4)0.66065 (10)0.0403 (4)
O20.71651 (7)0.0800 (4)0.63744 (11)0.0423 (4)
C10.71555 (8)0.1593 (5)0.64535 (13)0.0289 (5)
C20.66586 (7)0.2793 (5)0.63062 (12)0.0293 (5)
H20.64640.15100.64280.035*
C30.63792 (8)0.3610 (5)0.54654 (13)0.0354 (6)
H3A0.60710.43960.53950.042*
H3B0.65690.49320.53570.042*
C40.62701 (9)0.1422 (5)0.48853 (13)0.0357 (6)
H4A0.65760.06210.49490.043*
H4B0.60730.01060.49800.043*
C50.59988 (9)0.2409 (6)0.40709 (13)0.0383 (6)
H5A0.58920.09470.37190.046*
H5B0.57100.33680.40190.046*
N60.63148 (7)0.4091 (5)0.38769 (11)0.0389 (5)
H60.66260.39200.41400.047*
C70.61596 (8)0.5859 (6)0.33285 (13)0.0365 (6)
N80.56886 (7)0.6419 (5)0.29363 (11)0.0400 (5)
H8A0.55980.76080.25890.048*
H8B0.54730.55940.30280.048*
N90.64803 (8)0.7170 (6)0.31702 (14)0.0563 (7)
H9A0.63810.83500.28210.068*
H9B0.67880.68420.34170.068*
N110.80462 (7)0.5444 (4)0.80221 (10)0.0316 (4)
H11B0.83300.61380.80810.047*
H11A0.78790.66030.81560.047*
H11C0.78720.49960.75330.047*
O110.73012 (6)0.3320 (4)0.82595 (10)0.0404 (4)
O120.76753 (7)0.0507 (4)0.85604 (11)0.0445 (5)
C110.76612 (8)0.1854 (5)0.84259 (13)0.0300 (5)
C120.81424 (8)0.3108 (5)0.85139 (13)0.0301 (5)
H120.83260.18440.83620.036*
C130.84568 (9)0.3926 (5)0.93459 (13)0.0377 (6)
H13A0.87400.48730.93680.045*
H13B0.82670.51120.95010.045*
C140.86368 (9)0.1705 (6)0.99222 (13)0.0386 (6)
H14A0.88060.04340.97530.046*
H14B0.83580.08540.99460.046*
C150.89824 (9)0.2678 (6)1.07171 (14)0.0433 (6)
H15A0.91210.12061.10570.052*
H15B0.92500.36371.06880.052*
N160.87247 (7)0.4350 (5)1.10263 (11)0.0428 (6)
H160.84100.42901.08190.051*
C170.89471 (8)0.5954 (6)1.16071 (13)0.0388 (6)
N180.94234 (7)0.6326 (5)1.19129 (12)0.0482 (6)
H18A0.96000.55121.17350.058*
H18B0.95590.73841.22910.058*
N190.86868 (7)0.7287 (6)1.18907 (13)0.0553 (7)
H19A0.88310.83551.22640.066*
H19B0.83740.70811.17010.066*
O210.58452 (6)0.5899 (5)0.68366 (11)0.0548 (6)
O220.51710 (6)0.4846 (5)0.69392 (11)0.0569 (6)
C230.53977 (8)0.6177 (6)0.66600 (14)0.0385 (6)
C240.51014 (9)0.8179 (6)0.60773 (15)0.0445 (7)
H24A0.49770.94110.63290.053*
H24B0.48200.73080.56840.053*
C250.53524 (9)0.9697 (6)0.56855 (14)0.0417 (6)
H25A0.55300.84980.55120.050*
H25B0.55891.08650.60550.050*
C260.50001.1287 (8)0.50000.0431 (9)
H260.4811 (10)1.244 (6)0.5186 (15)0.054 (9)*
O310.96786 (6)0.5437 (5)0.82208 (11)0.0531 (5)
O320.88975 (7)0.5902 (5)0.79374 (12)0.0650 (7)
C330.93436 (9)0.6476 (6)0.83169 (14)0.0403 (6)
C340.94373 (10)0.8557 (7)0.89182 (17)0.0538 (8)
H34A0.92070.99610.86800.065*
H34B0.93600.78240.93140.065*
C350.99355 (9)0.9710 (6)0.92998 (14)0.0459 (7)
H35A0.99921.07980.89360.055*
H35B1.01780.83290.94600.055*
C361.00001.1344 (9)1.00000.0457 (9)
H361.0289 (9)1.248 (6)1.0138 (15)0.046 (8)*
OW10.73285 (8)0.8261 (5)0.96017 (15)0.0533 (6)
HW1A0.7399 (10)0.834 (7)0.9226 (16)0.050 (9)*
HW1B0.7412 (14)0.692 (9)0.978 (2)0.069 (14)*
OW20.76206 (8)0.7984 (6)0.54240 (15)0.0525 (5)
HW2A0.7514 (11)0.807 (7)0.5782 (17)0.058 (9)*
HW2B0.7563 (14)0.666 (9)0.528 (2)0.062 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0251 (9)0.0363 (12)0.0335 (10)0.0049 (9)0.0154 (8)0.0024 (9)
O10.0255 (8)0.0429 (11)0.0552 (10)0.0048 (8)0.0201 (7)0.0138 (9)
O20.0446 (10)0.0298 (10)0.0611 (12)0.0042 (8)0.0309 (9)0.0026 (9)
C10.0274 (11)0.0344 (14)0.0270 (11)0.0027 (10)0.0138 (9)0.0019 (10)
C20.0244 (10)0.0306 (12)0.0353 (11)0.0004 (10)0.0153 (9)0.0001 (10)
C30.0300 (11)0.0350 (14)0.0390 (12)0.0028 (10)0.0130 (10)0.0042 (11)
C40.0335 (12)0.0363 (14)0.0373 (12)0.0038 (11)0.0153 (10)0.0017 (11)
C50.0340 (12)0.0451 (16)0.0348 (12)0.0083 (11)0.0140 (10)0.0016 (12)
N60.0243 (9)0.0520 (14)0.0388 (11)0.0013 (10)0.0122 (8)0.0075 (11)
C70.0294 (11)0.0476 (16)0.0345 (12)0.0021 (12)0.0158 (10)0.0009 (12)
N80.0265 (10)0.0515 (14)0.0415 (11)0.0008 (10)0.0143 (8)0.0077 (11)
N90.0296 (11)0.0757 (19)0.0643 (14)0.0033 (12)0.0212 (10)0.0320 (15)
N110.0293 (9)0.0341 (11)0.0350 (10)0.0045 (9)0.0174 (8)0.0033 (9)
O110.0283 (8)0.0461 (11)0.0500 (10)0.0052 (8)0.0200 (7)0.0129 (9)
O120.0536 (11)0.0299 (10)0.0616 (12)0.0040 (9)0.0359 (10)0.0018 (9)
C110.0305 (12)0.0358 (14)0.0275 (11)0.0040 (11)0.0162 (9)0.0033 (10)
C120.0276 (11)0.0291 (12)0.0375 (12)0.0006 (10)0.0178 (9)0.0010 (11)
C130.0331 (12)0.0386 (15)0.0396 (13)0.0050 (11)0.0142 (10)0.0044 (12)
C140.0382 (12)0.0409 (15)0.0370 (13)0.0068 (12)0.0165 (10)0.0028 (12)
C150.0350 (12)0.0543 (17)0.0385 (13)0.0117 (13)0.0140 (11)0.0010 (13)
N160.0248 (9)0.0625 (16)0.0396 (11)0.0006 (11)0.0125 (9)0.0121 (12)
C170.0270 (11)0.0532 (17)0.0363 (12)0.0021 (12)0.0139 (10)0.0031 (12)
N180.0287 (10)0.0685 (17)0.0475 (12)0.0012 (11)0.0165 (9)0.0192 (13)
N190.0271 (10)0.079 (2)0.0607 (14)0.0043 (12)0.0198 (10)0.0292 (15)
O210.0297 (9)0.0762 (16)0.0649 (12)0.0154 (10)0.0264 (8)0.0195 (12)
O220.0349 (9)0.0723 (16)0.0699 (13)0.0145 (10)0.0289 (9)0.0298 (12)
C230.0298 (12)0.0487 (16)0.0395 (13)0.0054 (12)0.0173 (10)0.0004 (12)
C240.0312 (12)0.0550 (18)0.0511 (15)0.0067 (13)0.0214 (11)0.0083 (14)
C250.0332 (13)0.0486 (16)0.0414 (14)0.0042 (12)0.0145 (11)0.0008 (13)
C260.044 (2)0.040 (2)0.050 (2)0.0000.0243 (18)0.000
O310.0360 (9)0.0624 (13)0.0664 (12)0.0083 (10)0.0274 (9)0.0155 (12)
O320.0381 (10)0.0900 (18)0.0764 (13)0.0204 (12)0.0338 (10)0.0377 (14)
C330.0360 (13)0.0484 (16)0.0419 (13)0.0097 (12)0.0219 (11)0.0047 (13)
C340.0369 (13)0.066 (2)0.0612 (17)0.0055 (14)0.0236 (13)0.0141 (17)
C350.0409 (14)0.0511 (17)0.0451 (14)0.0073 (13)0.0182 (12)0.0009 (14)
C360.046 (2)0.041 (2)0.045 (2)0.0000.0140 (18)0.000
OW10.0506 (12)0.0610 (16)0.0600 (14)0.0068 (12)0.0349 (11)0.0084 (13)
OW20.0487 (12)0.0552 (16)0.0634 (14)0.0062 (11)0.0335 (11)0.0063 (13)
Geometric parameters (Å, º) top
N1—C21.489 (3)C14—C151.521 (3)
O1—C11.244 (3)C15—N161.453 (3)
O2—C11.242 (3)N16—C171.319 (3)
C1—C21.534 (3)C17—N181.313 (3)
C2—C31.531 (3)C17—N191.330 (3)
C3—C41.521 (4)O21—C231.253 (3)
C4—C51.513 (3)O22—C231.246 (3)
C5—N61.455 (3)C23—C241.502 (4)
N6—C71.319 (3)C24—C251.504 (4)
C7—N81.323 (3)C25—C261.528 (3)
C7—N91.323 (3)C26—C25i1.528 (3)
N11—C121.481 (3)O31—C331.230 (3)
O11—C111.247 (3)O32—C331.260 (3)
O12—C111.239 (3)C33—C341.514 (4)
C11—C121.533 (3)C34—C351.484 (4)
C12—C131.531 (3)C35—C361.533 (4)
C13—C141.522 (4)C36—C35ii1.533 (4)
O2—C1—O1126.3 (2)C14—C13—C12115.2 (2)
O2—C1—C2116.7 (2)C13—C14—C15111.4 (2)
O1—C1—C2117.0 (2)N16—C15—C14110.77 (19)
N1—C2—C3107.62 (19)C17—N16—C15123.7 (2)
N1—C2—C1110.93 (18)N18—C17—N16121.9 (2)
C3—C2—C1110.60 (18)N18—C17—N19118.1 (2)
C4—C3—C2115.1 (2)N16—C17—N19120.0 (2)
C5—C4—C3111.5 (2)O22—C23—O21123.6 (3)
N6—C5—C4110.37 (19)O22—C23—C24116.1 (2)
C7—N6—C5124.97 (19)O21—C23—C24120.3 (2)
N8—C7—N9118.2 (2)C23—C24—C25117.8 (2)
N8—C7—N6122.0 (2)C24—C25—C26113.59 (19)
N9—C7—N6119.8 (2)C25i—C26—C25115.3 (4)
O12—C11—O11126.4 (2)O31—C33—O32123.7 (3)
O12—C11—C12116.4 (2)O31—C33—C34122.1 (2)
O11—C11—C12117.1 (2)O32—C33—C34114.1 (2)
N11—C12—C13108.18 (19)C35—C34—C33118.4 (2)
N11—C12—C11110.97 (18)C34—C35—C36111.7 (2)
C13—C12—C11111.02 (18)C35ii—C36—C35113.5 (4)
Symmetry codes: (i) x+1, y, z+1; (ii) x+2, y, z+2.
(dl-lysin) top
Crystal data top
0.5(C7H10O4)·(C6H15N2O2)·0.2(C2H6O)·0.53(H2O)F(000) = 1050
Mr = 242.48Dx = 1.044 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 950 reflections
a = 32.811 (17) Åθ = 2.0–26.4°
b = 11.012 (6) ŵ = 0.08 mm1
c = 8.552 (4) ÅT = 293 K
β = 91.333 (9)°Plate, colourless
V = 3089 (3) Å30.72 × 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 tubeRint = 0.035
Graphite monochromatorθmax = 26.4°, θmin = 2.0°
ω–2/q scansh = 4040
12142 measured reflectionsk = 1313
3160 independent reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.232H 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 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
0.5(C7H10O4)·(C6H15N2O2)·0.2(C2H6O)·0.53(H2O)V = 3089 (3) Å3
Mr = 242.48Z = 8
Monoclinic, C2/cMo Kα radiation
a = 32.811 (17) ŵ = 0.08 mm1
b = 11.012 (6) ÅT = 293 K
c = 8.552 (4) Å0.72 × 0.21 × 0.04 mm
β = 91.333 (9)°
Data collection top
CCD area detector
diffractometer
2244 reflections with I > 2σ(I)
12142 measured reflectionsRint = 0.035
3160 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0690 restraints
wR(F2) = 0.232H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.49 e Å3
3160 reflectionsΔρmin = 0.25 e Å3
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
xyzUiso*/UeqOcc. (<1)
O110.11065 (7)0.2546 (3)0.0930 (3)0.0696 (10)
O120.14038 (6)0.0760 (2)0.0910 (2)0.0493 (7)
C130.10957 (8)0.1414 (3)0.1057 (3)0.0461 (10)
C14A0.0740 (5)0.0850 (13)0.1768 (19)0.069 (4)0.572
C150.03647 (10)0.1519 (4)0.2015 (5)0.0754 (15)
C160.000000.0837 (6)0.250000.097 (3)
C14B0.0680 (6)0.076 (2)0.122 (3)0.091 (7)0.428
O10.26174 (5)0.38740 (16)0.9151 (2)0.0336 (6)
O20.23276 (5)0.52576 (16)0.7595 (2)0.0359 (6)
N10.19004 (6)0.32790 (18)1.0436 (2)0.0278 (6)
N70.18818 (6)0.03582 (19)0.3625 (2)0.0318 (7)
C10.23149 (7)0.4368 (2)0.8520 (3)0.0258 (7)
C20.18953 (7)0.3820 (2)0.8839 (3)0.0257 (7)
C30.17919 (8)0.2819 (2)0.7659 (3)0.0314 (8)
C40.17215 (8)0.3273 (2)0.5991 (3)0.0355 (8)
C50.16148 (8)0.2228 (3)0.4857 (3)0.0369 (8)
C60.19882 (8)0.1502 (2)0.4454 (3)0.0337 (8)
O190.0762 (10)0.4859 (17)0.075 (5)0.175 (15)0.200
O200.0998 (3)0.4638 (9)0.2544 (18)0.136 (5)0.400
C170.0607 (8)0.529 (3)0.214 (7)0.17 (2)0.200
C180.0570 (7)0.667 (3)0.200 (5)0.120 (15)0.200
O210.0532 (17)0.604 (6)0.109 (7)0.19 (2)*0.130
H14B0.066840.014900.113080.0824*0.572
H15A0.042180.213350.280220.0906*
H14A0.083020.054040.277990.0824*0.572
H16A0.008250.031330.336260.1166*0.500
H16B0.008250.031330.163740.1166*0.500
H15B0.029450.194070.105030.0906*
H14C0.072170.001520.181230.1090*0.428
H14D0.057660.053470.018690.1090*0.428
H1A0.208890.269871.049690.0417*
H1B0.165690.296211.062630.0417*
H1C0.195830.385291.113970.0417*
H20.168740.445750.877110.0308*
H3A0.154840.240060.799050.0377*
H3B0.201280.223300.766630.0377*
H4A0.150090.385990.597420.0426*
H4B0.196540.368030.564450.0426*
H5A0.149210.255910.390590.0443*
H5B0.141690.169700.533160.0443*
H6A0.214080.131110.540710.0404*
H6B0.216160.198960.379830.0404*
H7A0.210900.004260.340510.0476*
H7B0.172740.009940.423170.0476*
H7C0.174530.053020.274120.0476*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.0432 (13)0.0646 (17)0.102 (2)0.0002 (12)0.0232 (13)0.0081 (15)
O120.0320 (10)0.0746 (15)0.0416 (12)0.0098 (10)0.0074 (8)0.0076 (10)
C130.0272 (14)0.066 (2)0.0456 (17)0.0004 (13)0.0101 (11)0.0019 (15)
C14A0.044 (6)0.054 (6)0.110 (9)0.008 (4)0.022 (5)0.012 (7)
C150.0377 (18)0.089 (3)0.101 (3)0.0021 (18)0.0326 (19)0.002 (2)
C160.040 (3)0.087 (4)0.167 (7)0.00000.046 (4)0.0000
C14B0.024 (6)0.099 (10)0.151 (18)0.033 (6)0.045 (9)0.079 (12)
O10.0261 (9)0.0361 (10)0.0386 (10)0.0028 (7)0.0030 (7)0.0076 (8)
O20.0363 (10)0.0349 (10)0.0366 (10)0.0031 (8)0.0030 (8)0.0121 (8)
N10.0281 (10)0.0298 (11)0.0257 (11)0.0033 (8)0.0057 (8)0.0012 (8)
N70.0344 (11)0.0338 (12)0.0273 (11)0.0012 (9)0.0055 (8)0.0020 (9)
C10.0304 (12)0.0242 (12)0.0231 (11)0.0007 (10)0.0053 (9)0.0023 (9)
C20.0279 (12)0.0254 (12)0.0238 (12)0.0018 (9)0.0031 (9)0.0004 (9)
C30.0387 (14)0.0284 (13)0.0273 (13)0.0055 (10)0.0032 (10)0.0018 (10)
C40.0464 (15)0.0307 (14)0.0294 (14)0.0046 (11)0.0021 (11)0.0020 (11)
C50.0419 (15)0.0386 (15)0.0300 (13)0.0066 (12)0.0057 (11)0.0065 (11)
C60.0377 (14)0.0334 (14)0.0300 (13)0.0016 (11)0.0023 (10)0.0060 (11)
O190.18 (2)0.049 (11)0.30 (4)0.004 (13)0.06 (3)0.009 (17)
O200.122 (8)0.093 (7)0.193 (12)0.044 (6)0.018 (8)0.021 (8)
C170.060 (15)0.070 (18)0.37 (6)0.006 (13)0.10 (3)0.01 (3)
C180.048 (12)0.094 (19)0.22 (4)0.018 (12)0.028 (16)0.05 (2)
Geometric parameters (Å, º) top
O11—C131.252 (5)C14B—H14D0.9712
O12—C131.250 (4)C14B—H14C0.9720
O1—C11.244 (3)C15—H15A0.9697
O2—C11.260 (3)C15—H15B0.9698
O19—C171.39 (7)C16—H16B0.9699
O19—O201.72 (4)C16—H16A0.9699
O20—C171.50 (3)C1—C21.533 (3)
N1—C21.490 (3)C2—C31.527 (3)
N7—C61.483 (3)C3—C41.524 (4)
N1—H1B0.8903C4—C51.540 (4)
N1—H1C0.8901C5—C61.510 (4)
N1—H1A0.8900C2—H20.9796
N7—H7B0.8899C3—H3A0.9703
N7—H7C0.8899C3—H3B0.9703
N7—H7A0.8902C4—H4B0.9698
C13—C14B1.55 (2)C4—H4A0.9702
C13—C14A1.466 (16)C5—H5A0.9702
C14A—C151.455 (16)C5—H5B0.9698
C14B—C151.50 (2)C6—H6A0.9697
C15—C161.480 (5)C6—H6B0.9702
C14A—H14A0.9699C17—C181.53 (5)
C14A—H14B0.9706
O1···O12i3.238 (3)C1···H6Bi3.0454
O1···N1ii2.868 (3)C1···H7Ai2.6420
O1···N12.700 (3)C3···H6A2.8070
O1···C6iii3.377 (3)C6···H3B2.8620
O1···C6i3.397 (4)C13···H1Bv2.5424
O1···N7iii2.974 (3)C13···H5A3.0117
O1···N7i3.038 (3)C13···H7C2.7243
O2···N7i2.899 (3)C13···H7Bvi2.9965
O2···N1iv2.802 (3)H1A···H3B2.4814
O2···C43.238 (3)H1A···O12.4698
O11···N1v2.769 (3)H1A···O1ii2.0013
O11···O192.79 (2)H1B···C13viii2.5424
O11···O202.713 (12)H1B···O11viii1.8869
O12···N72.807 (3)H1B···H3A2.3564
O12···O1i3.238 (3)H1B···O12viii2.5765
O12···N1v3.247 (3)H1C···O12.7822
O12···C6vi3.397 (4)H1C···C1vii3.0398
O12···N7vi2.817 (3)H1C···O2vii1.9765
O19···O112.79 (2)H2···O20vii2.6645
O19···O20iv2.92 (4)H2···H4A2.5418
O19···C17iv3.12 (7)H3A···H1B2.3564
O20···O112.713 (12)H3A···H5B2.4313
O20···O19vii2.92 (4)H3B···H6A2.2311
O1···H1C2.7822H3B···H7Ax2.5115
O1···H7Ci2.7530H3B···C62.8620
O1···H1A2.4698H3B···H1A2.4814
O1···H1Aii2.0013H4A···O19vii2.8077
O1···H7Aiii2.5515H4A···H22.5418
O1···H7Biii2.7702H4A···O20vii2.7137
O1···H7Ai2.7077H4B···H6B2.5339
O1···H6Bi2.8066H4B···C12.7937
O1···H6Aiii2.8215H4B···O22.6682
O2···H4B2.6682H4B···C1iv3.0548
O2···H1Civ1.9765H5A···O112.8157
O2···H6Aiii2.6775H5A···C133.0117
O2···H7Ai2.0684H5A···H7C2.5909
O11···H15B2.7506H5B···O12x2.7510
O11···H15A2.8257H5B···H7B2.4250
O11···H1Bv1.8869H5B···H3A2.4313
O11···H5A2.8157H6A···O2ix2.6775
O12···H5Bvi2.7510H6A···O1ix2.8215
O12···H7C1.9210H6A···C1ix2.9212
O12···H1Bv2.5765H6A···H3B2.2311
O12···H7Bvi1.9461H6A···C32.8070
O19···H4Aiv2.8077H6B···H4B2.5339
O20···H4Aiv2.7137H6B···O1i2.8066
O20···H2iv2.6645H6B···C1i3.0454
N1···O12.700 (3)H7A···O1i2.7077
N1···O11viii2.769 (3)H7A···O2i2.0684
N1···O2vii2.802 (3)H7A···O1ix2.5515
N1···O12viii3.247 (3)H7A···H3Bvi2.5115
N1···C13viii3.397 (4)H7A···C1i2.6420
N1···O1ii2.868 (3)H7B···C13x2.9965
N7···O1ix2.974 (3)H7B···O1ix2.7702
N7···O122.807 (3)H7B···H5B2.4250
N7···O12x2.817 (3)H7B···O12x1.9461
N7···C1i3.260 (4)H7C···H5A2.5909
N7···O1i3.038 (3)H7C···O121.9210
N7···O2i2.899 (3)H7C···C132.7243
C1···N7i3.260 (4)H7C···O1i2.7530
C1···C6i3.590 (4)H14C···H16A2.5285
C4···O23.238 (3)H14C···H16A2.5285
C6···O1ix3.377 (3)H14D···H16B2.5298
C6···C1i3.590 (4)H14D···H16B2.5298
C6···O12x3.397 (4)H14D···H16Bxi2.4118
C6···O1i3.397 (4)H14D···H16Avi2.4118
C13···N1v3.397 (4)H15A···H15Bxii2.5766
C17···O19vii3.12 (7)H15A···O112.8257
C1···H4Bvii3.0548H15B···O112.7506
C1···H6Aiii2.9212H15B···H15Axii2.5766
C1···H4B2.7937H16A···H14C2.5285
C1···H1Civ3.0398H16B···H14D2.5298
H1A—N1—H1C109.46H16A—C16—H16B107.03
H1B—N1—H1C109.45C15xii—C16—H16B107.56
C2—N1—H1B109.47C15—C16—H16B107.56
C2—N1—H1C109.48C15xii—C16—H16A107.56
C2—N1—H1A109.50C15—C16—H16A107.56
H1A—N1—H1B109.46O1—C1—O2125.1 (2)
C6—N7—H7A109.46O1—C1—C2117.5 (2)
C6—N7—H7B109.45O2—C1—C2117.4 (2)
C6—N7—H7C109.48N1—C2—C1109.24 (19)
H7A—N7—H7B109.47N1—C2—C3108.34 (18)
H7A—N7—H7C109.48C1—C2—C3110.7 (2)
H7B—N7—H7C109.49C2—C3—C4114.09 (19)
O11—C13—C14A118.8 (6)C3—C4—C5111.8 (2)
O11—C13—C14B119.8 (8)C4—C5—C6111.5 (2)
O11—C13—O12122.7 (3)N7—C6—C5112.1 (2)
O12—C13—C14A116.8 (6)N1—C2—H2109.50
O12—C13—C14B117.1 (8)C1—C2—H2109.53
C13—C14A—C15122.0 (10)C3—C2—H2109.53
C13—C14B—C15113.4 (14)C2—C3—H3A108.75
C14B—C15—C16114.4 (9)C2—C3—H3B108.74
C14A—C15—C16118.4 (7)C4—C3—H3A108.74
C15—C16—C15xii119.0 (5)C4—C3—H3B108.73
C13—C14A—H14A106.83H3A—C3—H3B107.60
H14A—C14A—H14B106.63C3—C4—H4A109.22
C13—C14A—H14B106.77C3—C4—H4B109.24
C15—C14A—H14A106.87C5—C4—H4A109.26
C15—C14A—H14B106.84C5—C4—H4B109.29
H14C—C14B—H14D107.49H4A—C4—H4B107.94
C15—C14B—H14D108.88C4—C5—H5A109.33
C13—C14B—H14C108.97C4—C5—H5B109.37
C15—C14B—H14C108.86C6—C5—H5A109.32
C13—C14B—H14D109.03C6—C5—H5B109.34
C14A—C15—H15B107.70H5A—C5—H5B107.98
C16—C15—H15A107.69N7—C6—H6A109.20
C16—C15—H15B107.68N7—C6—H6B109.17
C14A—C15—H15A107.68C5—C6—H6A109.20
H15A—C15—H15B107.14C5—C6—H6B109.20
C14B—C15—H15B91.94H6A—C6—H6B107.91
C14B—C15—H15A125.28O19—C17—C18108 (4)
O11—C13—C14A—C1513.7 (15)O2—C1—C2—C389.6 (3)
O12—C13—C14A—C15179.4 (9)C1—C2—C3—C467.8 (3)
C13—C14A—C15—C16170.3 (8)N1—C2—C3—C4172.4 (2)
C14A—C15—C16—C15xii170.9 (8)C2—C3—C4—C5179.5 (2)
O1—C1—C2—N131.2 (3)C3—C4—C5—C676.5 (3)
O1—C1—C2—C388.0 (3)C4—C5—C6—N7168.7 (2)
O2—C1—C2—N1151.2 (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, z1/2; (v) x, y, z1; (vi) x, y, z1/2; (vii) x, y+1, z+1/2; (viii) x, y, z+1; (ix) x+1/2, y1/2, 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···AD—HH···AD···AD—H···A
N1—H1A···O1ii0.89002.00132.868 (3)164.09
N1—H1B···O11viii0.89031.88692.769 (3)170.45
N1—H1B···O12viii0.89032.57653.247 (3)132.74
N1—H1C···O2vii0.89011.97652.802 (3)153.59
N7—H7A···O1ix0.89022.55152.974 (3)109.83
N7—H7A···O2i0.89022.06842.899 (3)154.82
N7—H7B···O12x0.88991.94612.817 (3)165.78
N7—H7C···O120.88991.92102.807 (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, y1/2, z+3/2; (x) x, y, z+1/2.

Experimental details

(arg)(dl-lysin)
Crystal data
Chemical formulaC19H44N8O100.5(C7H10O4)·(C6H15N2O2)·0.2(C2H6O)·0.53(H2O)
Mr544.62242.48
Crystal system, space groupMonoclinic, C2Monoclinic, C2/c
Temperature (K)293293
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)
V3)2713.2 (12)3089 (3)
Z48
Radiation typeMo KαMo Kα
µ (mm1)0.110.08
Crystal size (mm)0.42 × 0.07 × 0.060.72 × 0.21 × 0.04
Data collection
DiffractometerCCD 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
Rint0.0250.035
(sin θ/λ)max1)0.6250.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.094, 1.23 0.069, 0.232, 1.12
No. of reflections30973160
No. of parameters359190
No. of restraints10
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.160.49, 0.25
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881?
Absolute structure parameter10 (10)none

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1990), SHELXS97 <Sheldrick, 1990>, SHELXL97 (Sheldrick, 1997), SHELXL97 <Sheldrick, 1997>, ORTEP-3 for Windows (Farrugia, 1997), MSWORD XP, PLATON (Spek, 2003).

Selected geometric parameters (Å, º) for (dl-lysin) top
O11—C131.252 (5)O19—O201.72 (4)
O12—C131.250 (4)O20—C171.50 (3)
O1—C11.244 (3)N1—C21.490 (3)
O2—C11.260 (3)N7—C61.483 (3)
O19—C171.39 (7)
O11—C13—C14A118.8 (6)O1—C1—C2117.5 (2)
O11—C13—C14B119.8 (8)O2—C1—C2117.4 (2)
O11—C13—O12122.7 (3)N1—C2—C1109.24 (19)
O12—C13—C14A116.8 (6)N1—C2—C3108.34 (18)
O12—C13—C14B117.1 (8)N7—C6—C5112.1 (2)
O1—C1—O2125.1 (2)O19—C17—C18108 (4)
Hydrogen-bond geometry (Å, º) for (dl-lysin) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.89002.00132.868 (3)164.09
N1—H1B···O11ii0.89031.88692.769 (3)170.45
N1—H1B···O12ii0.89032.57653.247 (3)132.74
N1—H1C···O2iii0.89011.97652.802 (3)153.59
N7—H7A···O1iv0.89022.55152.974 (3)109.83
N7—H7A···O2v0.89022.06842.899 (3)154.82
N7—H7B···O12vi0.88991.94612.817 (3)165.78
N7—H7C···O120.88991.92102.807 (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, y1/2, z+3/2; (v) x+1/2, y+1/2, z+1; (vi) x, y, z+1/2.
 

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