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The complexes of glutaric acid with DL-lysine contain singly positively charged zwitterionic lysinium ions and singly negatively charged semi-glutarate ions. Both the ions exhibit different conformations in the two complexes. The structures contain head-to-tail sequences of amino acids. However, the aggregation patterns in the two complexes are entirely different, demonstrating the effect of chirality on molecular aggregation. These patterns also turn out to be different from those so far observed, in structures containing amino acids. The structures contain characteristic interaction patterns involving linear arrays of alternating amino and carboxylate groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810100218X/de0009sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810100218X/de0009Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810100218X/de0009IIsup3.hkl
Contains datablock II

CCDC references: 166511; 166512

Computing details top

For both compounds, data collection: CAD4; cell refinement: CAD4; data reduction: CAD4; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP III. Software used to prepare material for publication: MS Word for (I); MS WORD for (II).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
(I) top
Crystal data top
C6H15N2O2·C5H7O4F(000) = 600
Mr = 278.31Dx = 1.335 Mg m3
Monoclinic, IaCu Kα radiation, λ = 1.54180 Å
a = 10.398 (6) ÅCell parameters from 25 reflections
b = 8.662 (2) Åθ = 10–30°
c = 15.393 (6) ŵ = 0.92 mm1
β = 93.06 (2)°T = 293 K
V = 1384.4 (10) Å3Rectangular, colourless
Z = 40.8 × 0.5 × 0.2 mm
Data collection top
CAD4
diffractometer
1382 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 75.2°, θmin = 5.8°
ω–2/q scansh = 013
Absorption correction: for a cylinder mounted on the ϕ axis
Dwiggins JR Acta.Cryst 1975, A31,146
k = 010
Tmin = 0.714, Tmax = 0.728l = 1919
2138 measured reflections3 standard reflections every 60 min
1426 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.0986P)2 + 0.2437P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.152(Δ/σ)max < 0.001
S = 1.30Δρmax = 0.28 e Å3
1426 reflectionsΔρmin = 0.25 e Å3
174 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.0038 (10)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map
Crystal data top
C6H15N2O2·C5H7O4V = 1384.4 (10) Å3
Mr = 278.31Z = 4
Monoclinic, IaCu Kα radiation
a = 10.398 (6) ŵ = 0.92 mm1
b = 8.662 (2) ÅT = 293 K
c = 15.393 (6) Å0.8 × 0.5 × 0.2 mm
β = 93.06 (2)°
Data collection top
CAD4
diffractometer
1426 independent reflections
Absorption correction: for a cylinder mounted on the ϕ axis
Dwiggins JR Acta.Cryst 1975, A31,146
1382 reflections with I > 2σ(I)
Tmin = 0.714, Tmax = 0.728Rint = 0.020
2138 measured reflections3 standard reflections every 60 min
Refinement top
R[F2 > 2σ(F2)] = 0.0402 restraints
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 1.30Δρmax = 0.28 e Å3
1426 reflectionsΔρmin = 0.25 e Å3
174 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
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
N10.8492 (3)0.0830 (3)0.28982 (18)0.0388 (6)
H1C0.83930.06670.23280.058*
H1B0.90380.01370.31340.058*
H1A0.88030.17750.29960.058*
O10.6747 (3)0.2904 (4)0.2421 (2)0.0621 (8)
O20.5131 (2)0.1704 (3)0.3029 (2)0.0508 (6)
C10.6300 (3)0.1872 (3)0.2858 (2)0.0361 (6)
C20.7230 (3)0.0680 (3)0.32933 (19)0.0326 (6)
H20.68900.03610.31820.039*
C30.7365 (3)0.0953 (4)0.4275 (2)0.0383 (7)
H3A0.77020.19850.43760.046*
H3B0.65130.09190.45020.046*
C40.8218 (4)0.0175 (4)0.4788 (2)0.0439 (7)
H4A0.91060.00240.46440.053*
H4B0.79720.12220.46300.053*
C50.8107 (3)0.0046 (4)0.5762 (2)0.0425 (7)
H5A0.82950.11140.59100.051*
H5B0.72280.01650.59070.051*
C60.9004 (4)0.0984 (4)0.6298 (2)0.0441 (7)
H6A0.88300.20510.61400.053*
H6B0.98840.07560.61630.053*
N70.8870 (3)0.0794 (4)0.7241 (2)0.0458 (7)
H7A0.94170.14220.75300.069*
H7B0.80680.10230.73700.069*
H7C0.90440.01790.73910.069*
O110.4743 (3)0.6461 (4)0.3567 (2)0.0556 (7)
O120.6622 (3)0.6816 (3)0.29923 (17)0.0515 (6)
C130.5933 (3)0.6281 (4)0.3572 (2)0.0386 (7)
C140.6633 (3)0.5360 (4)0.4289 (2)0.0432 (7)
H14A0.71710.60600.46400.052*
H14B0.71980.46260.40240.052*
C150.5770 (4)0.4483 (4)0.4886 (3)0.0480 (8)
H15A0.51340.39130.45310.058*
H15B0.62900.37370.52180.058*
C160.5078 (4)0.5492 (5)0.5512 (2)0.0460 (8)
H16A0.46630.63330.51890.055*
H16B0.44080.48870.57660.055*
C170.5935 (3)0.6157 (4)0.6233 (2)0.0387 (7)
O180.7053 (3)0.5818 (4)0.63856 (19)0.0591 (8)
O190.5326 (3)0.7166 (4)0.66971 (18)0.0542 (7)
H190.57350.73130.71600.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0354 (14)0.0474 (14)0.0338 (12)0.0027 (10)0.0035 (10)0.0001 (10)
O10.0501 (16)0.0596 (16)0.076 (2)0.0030 (12)0.0016 (13)0.0320 (14)
O20.0307 (11)0.0565 (14)0.0645 (16)0.0005 (10)0.0046 (10)0.0095 (12)
C10.0329 (14)0.0408 (14)0.0341 (14)0.0034 (11)0.0043 (10)0.0007 (11)
C20.0279 (13)0.0356 (13)0.0341 (14)0.0023 (10)0.0011 (10)0.0002 (10)
C30.0388 (15)0.0427 (14)0.0334 (14)0.0057 (12)0.0018 (11)0.0019 (11)
C40.0520 (18)0.0464 (17)0.0328 (15)0.0133 (14)0.0039 (13)0.0001 (12)
C50.0421 (16)0.0486 (17)0.0366 (15)0.0082 (13)0.0005 (12)0.0022 (12)
C60.0423 (17)0.0519 (17)0.0378 (16)0.0098 (13)0.0002 (13)0.0020 (13)
N70.0393 (15)0.0569 (17)0.0403 (15)0.0062 (12)0.0056 (11)0.0068 (12)
O110.0413 (13)0.0697 (17)0.0558 (15)0.0114 (12)0.0024 (11)0.0151 (13)
O120.0487 (14)0.0611 (14)0.0452 (14)0.0046 (11)0.0066 (10)0.0179 (11)
C130.0408 (16)0.0367 (14)0.0380 (15)0.0030 (12)0.0001 (12)0.0002 (11)
C140.0456 (17)0.0469 (16)0.0371 (15)0.0095 (13)0.0031 (13)0.0024 (13)
C150.066 (2)0.0391 (15)0.0393 (15)0.0006 (15)0.0057 (15)0.0014 (13)
C160.0427 (17)0.0558 (18)0.0397 (17)0.0033 (14)0.0041 (13)0.0030 (14)
C170.0386 (16)0.0467 (15)0.0314 (13)0.0014 (12)0.0062 (11)0.0043 (12)
O180.0478 (15)0.088 (2)0.0415 (13)0.0161 (14)0.0003 (10)0.0026 (13)
O190.0455 (14)0.0676 (17)0.0492 (15)0.0099 (12)0.0002 (11)0.0149 (12)
Geometric parameters (Å, º) top
N1—C21.481 (4)O11—C131.246 (4)
O1—C11.226 (4)O12—C131.262 (4)
O2—C11.266 (4)C13—C141.517 (4)
C1—C21.543 (4)C14—C151.521 (5)
C2—C31.528 (4)C15—C161.512 (5)
C3—C41.514 (4)C16—C171.500 (5)
C4—C51.521 (4)C17—O181.210 (5)
C5—C61.505 (4)C17—O191.313 (4)
C6—N71.475 (5)
O1—C1—O2126.5 (3)O11—C13—O12123.4 (3)
O1—C1—C2118.6 (3)O11—C13—C14120.6 (3)
O2—C1—C2114.8 (3)O12—C13—C14116.1 (3)
N1—C2—C3110.9 (2)C13—C14—C15115.2 (3)
N1—C2—C1108.1 (2)C16—C15—C14114.4 (3)
C3—C2—C1110.4 (2)C17—C16—C15114.2 (3)
C4—C3—C2115.9 (3)O18—C17—O19122.9 (3)
C3—C4—C5111.1 (3)O18—C17—C16125.2 (3)
C6—C5—C4112.8 (3)O19—C17—C16111.9 (3)
N7—C6—C5112.6 (3)
(II) top
Crystal data top
C6H15N2O2·C5H7O4Dx = 1.310 Mg m3
Mr = 278.31Cu Kα radiation, λ = 1.54180 Å
Trigonal, P31Cell parameters from 25 reflections
a = 9.044 (1) Åθ = 10–30°
c = 14.943 (3) ŵ = 0.90 mm1
V = 1058.5 (3) Å3T = 293 K
Z = 3Needle, colourless
F(000) = 4501 × 0.44 × 0.31 mm
Data collection top
CAD4
diffractometer
1387 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.050
Graphite monochromatorθmax = 75.6°, θmin = 5.7°
ω–2/q scansh = 09
Absorption correction: empirical
North et al ., 1968
k = 09
Tmin = 0.945, Tmax = 1.000l = 1718
1745 measured reflections3 standard reflections every 60 min
1452 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.063 w = 1/[σ2(Fo2) + (0.0208P)2 + 1.5074P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.142(Δ/σ)max < 0.001
S = 1.19Δρmax = 0.31 e Å3
1452 reflectionsΔρmin = 0.31 e Å3
174 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.035 (2)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map
Crystal data top
C6H15N2O2·C5H7O4Z = 3
Mr = 278.31Cu Kα radiation
Trigonal, P31µ = 0.90 mm1
a = 9.044 (1) ÅT = 293 K
c = 14.943 (3) Å1 × 0.44 × 0.31 mm
V = 1058.5 (3) Å3
Data collection top
CAD4
diffractometer
1452 independent reflections
Absorption correction: empirical
North et al ., 1968
1387 reflections with I > 2σ(I)
Tmin = 0.945, Tmax = 1.000Rint = 0.050
1745 measured reflections3 standard reflections every 60 min
Refinement top
R[F2 > 2σ(F2)] = 0.0631 restraint
wR(F2) = 0.142H atoms treated by a mixture of independent and constrained refinement
S = 1.19Δρmax = 0.31 e Å3
1452 reflectionsΔρmin = 0.31 e Å3
174 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
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
N10.6198 (6)0.3550 (6)0.6881 (3)0.0365 (10)
H1C0.66120.30200.72110.055*
H1B0.69840.42300.64870.055*
H1A0.52710.27800.65910.055*
O10.3256 (5)0.1988 (5)0.7860 (2)0.0408 (9)
O20.4578 (5)0.3893 (5)0.8954 (2)0.0434 (10)
C10.4429 (6)0.3382 (7)0.8160 (3)0.0327 (11)
C20.5742 (6)0.4590 (6)0.7475 (3)0.0321 (11)
H20.67660.54470.77880.038*
C30.5037 (8)0.5484 (8)0.6898 (4)0.0407 (12)
H3A0.40960.46290.65450.049*
H3B0.59210.62380.64840.049*
C40.4413 (8)0.6522 (7)0.7414 (4)0.0414 (12)
H4A0.36240.58120.78770.050*
H4B0.53780.74770.77040.050*
C50.3536 (8)0.7185 (8)0.6813 (4)0.0462 (14)
H5A0.27070.62570.64440.055*
H5B0.43760.80470.64170.055*
C60.2643 (8)0.7947 (8)0.7328 (4)0.0436 (13)
H6A0.19300.71500.77870.052*
H6B0.34880.89850.76220.052*
N70.1576 (6)0.8343 (6)0.6737 (3)0.0402 (11)
H7A0.10690.87890.70600.060*
H7B0.07870.73890.64740.060*
H7C0.22310.90890.63210.060*
O110.5053 (6)0.3213 (5)0.4835 (3)0.0561 (12)
O120.3790 (7)0.1100 (6)0.5797 (3)0.0656 (15)
C130.4068 (7)0.1673 (8)0.5009 (4)0.0412 (12)
C140.3183 (8)0.0438 (7)0.4251 (4)0.0417 (13)
H14A0.21930.05720.44850.050*
H14B0.39530.00880.40040.050*
C150.2610 (8)0.1187 (8)0.3501 (4)0.0442 (13)
H15A0.18880.15970.37470.053*
H15B0.36020.21500.32340.053*
C160.1637 (7)0.0138 (7)0.2789 (4)0.0403 (13)
H16A0.23840.04900.25140.048*
H16B0.06900.11340.30630.048*
C170.0968 (7)0.0567 (8)0.2081 (4)0.0390 (12)
O180.1561 (7)0.0931 (7)0.1335 (3)0.0634 (14)
O190.0300 (6)0.0744 (7)0.2349 (3)0.0592 (13)
H190.04980.12860.19750.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.040 (2)0.047 (3)0.025 (2)0.024 (2)0.0012 (17)0.0008 (18)
O10.0302 (18)0.042 (2)0.035 (2)0.0064 (16)0.0021 (15)0.0037 (16)
O20.050 (2)0.050 (2)0.0277 (19)0.0233 (19)0.0027 (16)0.0015 (16)
C10.032 (2)0.045 (3)0.024 (2)0.021 (2)0.0024 (19)0.005 (2)
C20.027 (2)0.033 (3)0.029 (2)0.010 (2)0.0044 (19)0.0022 (19)
C30.047 (3)0.048 (3)0.033 (3)0.028 (3)0.005 (2)0.008 (2)
C40.048 (3)0.046 (3)0.037 (3)0.029 (3)0.004 (2)0.002 (2)
C50.057 (4)0.054 (3)0.036 (3)0.034 (3)0.001 (3)0.006 (3)
C60.056 (4)0.045 (3)0.033 (3)0.028 (3)0.008 (2)0.001 (2)
N70.049 (3)0.046 (3)0.030 (2)0.028 (2)0.002 (2)0.0001 (19)
O110.062 (3)0.047 (3)0.035 (2)0.010 (2)0.001 (2)0.0024 (19)
O120.080 (3)0.055 (3)0.028 (2)0.007 (2)0.010 (2)0.0029 (19)
C130.042 (3)0.050 (3)0.032 (3)0.023 (3)0.001 (2)0.004 (2)
C140.051 (3)0.040 (3)0.032 (3)0.022 (3)0.011 (2)0.001 (2)
C150.049 (3)0.046 (3)0.036 (3)0.022 (3)0.009 (2)0.001 (2)
C160.044 (3)0.049 (3)0.035 (3)0.029 (3)0.011 (2)0.001 (2)
C170.043 (3)0.050 (3)0.026 (2)0.025 (3)0.007 (2)0.002 (2)
O180.077 (3)0.100 (4)0.038 (2)0.062 (3)0.013 (2)0.021 (2)
O190.060 (3)0.100 (4)0.036 (2)0.054 (3)0.007 (2)0.014 (2)
Geometric parameters (Å, º) top
N1—C21.494 (6)O11—C131.249 (7)
O1—C11.256 (6)O12—C131.261 (7)
O2—C11.256 (6)C13—C141.509 (7)
C1—C21.535 (6)C14—C151.527 (7)
C2—C31.523 (7)C15—C161.512 (8)
C3—C41.525 (8)C16—C171.510 (7)
C4—C51.508 (7)C17—O181.209 (7)
C5—C61.509 (8)C17—O191.298 (7)
C6—N71.478 (7)
O2—C1—O1126.0 (5)O11—C13—O12122.5 (5)
O2—C1—C2117.8 (5)O11—C13—C14119.2 (5)
O1—C1—C2116.2 (4)O12—C13—C14118.3 (5)
N1—C2—C3108.6 (4)C13—C14—C15113.2 (5)
N1—C2—C1107.9 (4)C16—C15—C14110.9 (5)
C3—C2—C1112.1 (4)C17—C16—C15110.8 (5)
C2—C3—C4115.0 (4)O18—C17—O19123.4 (5)
C5—C4—C3111.9 (5)O18—C17—C16122.9 (5)
C4—C5—C6112.7 (5)O19—C17—C16113.7 (5)
N7—C6—C5111.6 (5)

Experimental details

(I)(II)
Crystal data
Chemical formulaC6H15N2O2·C5H7O4C6H15N2O2·C5H7O4
Mr278.31278.31
Crystal system, space groupMonoclinic, IaTrigonal, P31
Temperature (K)293293
a, b, c (Å)10.398 (6), 8.662 (2), 15.393 (6)9.044 (1), 9.044 (1), 14.943 (3)
α, β, γ (°)90, 93.06 (2), 9090, 90, 120
V3)1384.4 (10)1058.5 (3)
Z43
Radiation typeCu KαCu Kα
µ (mm1)0.920.90
Crystal size (mm)0.8 × 0.5 × 0.21 × 0.44 × 0.31
Data collection
DiffractometerCAD4
diffractometer
CAD4
diffractometer
Absorption correctionFor a cylinder mounted on the ϕ axis
Dwiggins JR Acta.Cryst 1975, A31,146
Empirical
North et al ., 1968
Tmin, Tmax0.714, 0.7280.945, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
2138, 1426, 1382 1745, 1452, 1387
Rint0.0200.050
(sin θ/λ)max1)0.6270.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.152, 1.30 0.063, 0.142, 1.19
No. of reflections14261452
No. of parameters174174
No. of restraints21
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)0.28, 0.250.31, 0.31
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881

Computer programs: CAD4, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP III, MS Word, MS WORD.

 

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