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To elucidate the structural features of amino acids caused by the C-terminal α-amidation, the crystal structures of HCl salts of C-terminal amidated Ile, Val, Thr, Ser, Met, Trp, Gln and Arg were analysed and compared with those of their C-terminal free acids. The bonding parameter of the amide group was little affected by the different chemical properties of the side chains. As for the molecular packing patterns, some structural differences were observed by the C-amidation. The Cα—H...O hydrogen bonds and carbonyl–carbonyl interactions were more strengthened by the salt formation with HCl in C-amides than C-acids. Furthermore, there is a clear difference between the interaction patterns with Cl ions. In most C-amide crystals, Cl ions are bifurcately hydrogen-bonded to two neighbouring amide NH2 groups and the parallel layers of the C-amides and Cl ions are alternatively formed. In the case of the carboxyl OH in C-acid crystals, however, the direct hydrogen bond with the Cl ion is not always observed and is largely dependent on the crystal packing environment. This suggests the superior hydrogen-bonding ability of NH...Cl compared with OH...Cl. The difference in hydrogen-bonding ability between the amide and carboxyl groups is considered, based on the spatial dispositions of the hydrogen-bonding polar atoms/groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768100013975/oa0030sup1.cif
Contains datablocks ileNH2, valNH2, thrNH2, serNH2, metNH2, trpNH2, argNH2, global, glnNH2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100013975/oa0030ileNH2sup2.hkl
Contains datablock ile-amide

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100013975/oa0030valNH2sup3.hkl
Contains datablock val-amide

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100013975/oa0030thrNH2sup4.hkl
Contains datablock thr-nh2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100013975/oa0030metNH2sup5.hkl
Contains datablock met-nh2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100013975/oa0030trpNH2sup6.hkl
Contains datablock trp-nh2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100013975/oa0030glnNH2sup7.hkl
Contains datablock gln-nh2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100013975/oa0030argNH2sup8.hkl
Contains datablock arg-nh2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100013975/oa0030serNH2sup9.hkl
Contains datablock ser-nh2

CCDC references: 159961; 159962; 159963; 159964; 159965; 159966; 159967; 159968

Computing details top

For all compounds, data collection: MSC/AFC (Molecular Structure Corp. 1991); cell refinement: MSC/AFC (Molecular Structure Corp. 1991); data reduction: MSC/AFC (Molecular Structure Corp. 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
(ileNH2) top
Crystal data top
C6H15N2O+·ClF(000) = 180
Mr = 166.65Dx = 1.190 Mg m3
Dm = 1.221 (5) Mg m3
Dm measured by measured
Monoclinic, P21Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2y1Cell parameters from 25 reflections
a = 7.5775 (13) Åθ = 0.3–65.0°
b = 4.8971 (13) ŵ = 3.20 mm1
c = 12.5686 (14) ÅT = 293 K
β = 94.195 (12)°Plate, colourless
V = 465.14 (16) Å30.6 × 0.4 × 0.05 mm
Z = 2
Data collection top
Rigaku AFC5R
diffractometer
817 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.052
Graphite monochromatorθmax = 65.0°, θmin = 3.5°
ω–2θ scansh = 08
Absorption correction: ψ-scan
North, et al., 1990
k = 50
Tmin = 0.629, Tmax = 0.999l = 1414
963 measured reflections3 standard reflections every 100 reflections
893 independent reflections intensity decay: 2%
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)] = 0.069H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.187Calculated w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.66(Δ/σ)max = 0.094
893 reflectionsΔρmax = 0.70 e Å3
90 parametersΔρmin = 0.29 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.04 (5)
Crystal data top
C6H15N2O+·ClV = 465.14 (16) Å3
Mr = 166.65Z = 2
Monoclinic, P21Cu Kα radiation
a = 7.5775 (13) ŵ = 3.20 mm1
b = 4.8971 (13) ÅT = 293 K
c = 12.5686 (14) Å0.6 × 0.4 × 0.05 mm
β = 94.195 (12)°
Data collection top
Rigaku AFC5R
diffractometer
817 reflections with I > 2σ(I)
Absorption correction: ψ-scan
North, et al., 1990
Rint = 0.052
Tmin = 0.629, Tmax = 0.9993 standard reflections every 100 reflections
963 measured reflections intensity decay: 2%
893 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.069H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.187Δρmax = 0.70 e Å3
S = 1.66Δρmin = 0.29 e Å3
893 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
90 parametersAbsolute structure parameter: 0.04 (5)
0 restraints
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 > 2σ(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
Cl10.52108 (13)0.65040.62484 (10)0.0460 (5)
N10.2267 (5)1.1570 (14)0.5937 (3)0.0364 (9)
H1A0.21031.16210.52190.044*
H1B0.28030.98930.60140.044*
H1C0.29701.31290.60520.044*
C10.0721 (6)1.1726 (14)0.6735 (3)0.0345 (11)
H10.03751.36370.68530.041*
C1'0.0777 (7)1.0162 (14)0.6266 (4)0.0359 (11)
O1'0.0556 (5)0.7854 (10)0.5938 (3)0.0409 (9)
N20.2334 (5)1.1489 (16)0.6269 (4)0.0498 (11)
H2NA0.25241.36140.64160.060*
H2NB0.32201.06140.60190.060*
C20.1145 (7)1.0406 (16)0.7800 (4)0.0442 (13)
H20.15400.85300.76510.053*
C30.2628 (9)1.1903 (18)0.8297 (5)0.063 (2)
H3A0.21841.36410.85740.075*
H3B0.35641.22780.77490.075*
C40.0499 (11)1.028 (3)0.8553 (5)0.086 (3)
H4A0.02220.94140.92060.130*
H4B0.09261.20920.87010.130*
H4C0.13930.92390.82310.130*
C50.3392 (14)1.033 (3)0.9187 (7)0.093 (3)
H5A0.43231.13790.94680.139*
H5B0.24810.99950.97430.139*
H5C0.38570.86260.89170.139*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0287 (7)0.0366 (7)0.0725 (8)0.0020 (6)0.0025 (5)0.0008 (7)
N10.0270 (17)0.039 (2)0.0435 (18)0.000 (3)0.0066 (14)0.002 (3)
C10.024 (2)0.032 (3)0.047 (2)0.001 (2)0.0026 (17)0.005 (3)
C1'0.030 (2)0.033 (3)0.044 (2)0.002 (3)0.0024 (18)0.000 (2)
O1'0.0277 (17)0.036 (2)0.0596 (19)0.0024 (16)0.0095 (15)0.0081 (18)
N20.0231 (19)0.045 (2)0.082 (3)0.004 (3)0.0072 (18)0.009 (4)
C20.045 (3)0.044 (3)0.044 (3)0.006 (3)0.003 (2)0.001 (3)
C30.069 (4)0.067 (5)0.055 (3)0.026 (4)0.025 (3)0.011 (3)
C40.071 (5)0.137 (9)0.050 (3)0.010 (6)0.009 (3)0.012 (5)
C50.109 (7)0.097 (7)0.078 (5)0.023 (6)0.050 (5)0.016 (5)
Geometric parameters (Å, º) top
N1—C11.487 (5)C1'—N21.347 (8)
C1—C1'1.523 (7)C2—C41.510 (8)
C1—C21.541 (7)C2—C31.515 (8)
C1'—O1'1.211 (7)C3—C51.507 (11)
N1—C1—C1'106.6 (4)N2—C1'—C1115.7 (5)
N1—C1—C2111.1 (4)C4—C2—C1110.3 (5)
C1'—C1—C2109.5 (5)C4—C2—C3111.4 (5)
O1'—C1'—N2123.4 (6)C1—C2—C3111.3 (5)
O1'—C1'—C1120.9 (5)C5—C3—C2113.3 (7)
(valNH2) top
Crystal data top
C5H13N2O+·ClF(000) = 164
Mr = 152.62Dx = 1.287 Mg m3
Dm = 1.280 (5) Mg m3
Dm measured by measured
Monoclinic, P21Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2y1Cell parameters from 25 reflections
a = 5.3377 (8) Åθ = 0.3–65.0°
b = 7.4572 (9) ŵ = 3.73 mm1
c = 9.899 (1) ÅT = 293 K
β = 91.73 (1)°Plate, colourless
V = 393.84 (9) Å30.8 × 0.6 × 0.3 mm
Z = 2
Data collection top
Rigaku AFC5R
diffractometer
Rint = 0.135
Radiation source: fine-focus sealed tubeθmax = 65.0°, θmin = 4.5°
Graphite monochromatorh = 66
ω–2θ scansk = 80
1458 measured reflectionsl = 1111
731 independent reflections3 standard reflections every 100 reflections
718 reflections with I > 2σ(I) intensity decay: 2%
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)] = 0.037Calculated w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.097(Δ/σ)max = 0.176
S = 0.75Δρmax = 0.30 e Å3
731 reflectionsΔρmin = 0.41 e Å3
82 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2]3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.67 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.009 (16)
Crystal data top
C5H13N2O+·ClV = 393.84 (9) Å3
Mr = 152.62Z = 2
Monoclinic, P21Cu Kα radiation
a = 5.3377 (8) ŵ = 3.73 mm1
b = 7.4572 (9) ÅT = 293 K
c = 9.899 (1) Å0.8 × 0.6 × 0.3 mm
β = 91.73 (1)°
Data collection top
Rigaku AFC5R
diffractometer
Rint = 0.135
1458 measured reflections3 standard reflections every 100 reflections
731 independent reflections intensity decay: 2%
718 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097(Δ/σ)max = 0.176
S = 0.75Δρmax = 0.30 e Å3
731 reflectionsΔρmin = 0.41 e Å3
82 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
0 restraintsAbsolute structure parameter: 0.009 (16)
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 > 2σ(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
Cl10.31763 (9)0.33930.66340 (4)0.0355 (4)
N10.2346 (4)0.3958 (3)0.60582 (16)0.0272 (6)
H1A0.34410.48220.62260.033*
H1B0.25730.36790.52300.033*
H1C0.06350.45620.63530.033*
C10.3014 (4)0.2353 (3)0.68810 (17)0.0220 (5)
H10.46200.18820.65320.026*
C1'0.1014 (5)0.0951 (4)0.66654 (18)0.0256 (6)
O1'0.1097 (3)0.1416 (3)0.63338 (18)0.0365 (6)
N20.1632 (5)0.0743 (4)0.6891 (3)0.0444 (7)
H2NA0.05090.16240.67140.053*
H2NB0.33800.12940.68440.053*
C20.3316 (4)0.2894 (4)0.83690 (17)0.0277 (7)
H20.45410.38730.83820.033*
C30.0910 (6)0.3589 (5)0.9032 (3)0.0469 (8)
H3A0.02720.45610.85080.070*
H3B0.12400.40050.99270.070*
H3C0.03070.26410.90820.070*
C40.4375 (5)0.1360 (5)0.9175 (2)0.0443 (8)
H4A0.58920.09380.87370.067*
H4B0.31760.04010.92290.067*
H4C0.47280.17671.00690.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0345 (5)0.0361 (5)0.0363 (5)0.0124 (3)0.0065 (2)0.0077 (2)
N10.0302 (11)0.0277 (10)0.0240 (8)0.0050 (9)0.0068 (7)0.0021 (7)
C10.0170 (10)0.0272 (11)0.0221 (8)0.0010 (9)0.0034 (7)0.0009 (8)
C1'0.0275 (11)0.0250 (11)0.0245 (10)0.0036 (12)0.0037 (7)0.0007 (8)
O1'0.0198 (9)0.0397 (12)0.0504 (9)0.0018 (9)0.0088 (6)0.0035 (8)
N20.0392 (15)0.0257 (11)0.0692 (13)0.0018 (12)0.0175 (11)0.0017 (12)
C20.0271 (13)0.0341 (16)0.0223 (11)0.0070 (10)0.0070 (9)0.0002 (8)
C30.0467 (16)0.0622 (18)0.0317 (10)0.0034 (16)0.0008 (10)0.0143 (14)
C40.0445 (14)0.055 (2)0.0347 (11)0.0070 (16)0.0133 (11)0.0124 (13)
Geometric parameters (Å, º) top
N1—C11.497 (3)C1'—N21.327 (4)
C1—C1'1.514 (4)C2—C31.516 (4)
C1—C21.540 (2)C2—C41.514 (4)
C1'—O1'1.233 (3)
N1—C1—C1'107.15 (15)N2—C1'—C1117.0 (2)
N1—C1—C2110.2 (2)C3—C2—C4110.8 (2)
C1'—C1—C2114.23 (18)C3—C2—C1113.06 (17)
O1'—C1'—N2123.1 (3)C4—C2—C1110.9 (3)
O1'—C1'—C1119.8 (2)
(thrNH2) top
Crystal data top
C4H11N2O2+·ClDx = 1.417 Mg m3
Dm = 1.402 (5) Mg m3
Dm measured by measured
Mr = 154.60Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 10.1624 (15) Åθ = 0.3–63.1°
b = 10.5673 (17) ŵ = 4.17 mm1
c = 6.749 (3) ÅT = 293 K
V = 724.8 (3) Å3Cubic, colourless
Z = 40.8 × 0.6 × 0.6 mm
F(000) = 328
Data collection top
Rigaku AFC5R
diffractometer
710 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 63.1°, θmin = 6.0°
ω–2θ scansh = 011
Absorption correction: ψ-scan
North, et al., 1990
k = 012
Tmin = 0.782, Tmax = 0.999l = 70
710 measured reflections3 standard reflections every 100 reflections
710 independent reflections intensity decay: 2%
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)] = 0.047Calculated w = 1/[σ2(Fo2) + (0.0986P)2 + 0.4071P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.121(Δ/σ)max = 0.049
S = 1.10Δρmax = 0.50 e Å3
710 reflectionsΔρmin = 0.59 e Å3
83 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.34 (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 mapAbsolute structure parameter: 0.06 (3)
Crystal data top
C4H11N2O2+·ClV = 724.8 (3) Å3
Mr = 154.60Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 10.1624 (15) ŵ = 4.17 mm1
b = 10.5673 (17) ÅT = 293 K
c = 6.749 (3) Å0.8 × 0.6 × 0.6 mm
Data collection top
Rigaku AFC5R
diffractometer
710 reflections with I > 2σ(I)
Absorption correction: ψ-scan
North, et al., 1990
Rint = 0.000
Tmin = 0.782, Tmax = 0.9993 standard reflections every 100 reflections
710 measured reflections intensity decay: 2%
710 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121Δρmax = 0.50 e Å3
S = 1.10Δρmin = 0.59 e Å3
710 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
83 parametersAbsolute structure parameter: 0.06 (3)
0 restraints
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
Cl10.96087 (8)0.37191 (8)0.35803 (13)0.0172 (5)
N10.6071 (3)0.8326 (3)0.5331 (4)0.0130 (8)
H1A0.59840.76780.63150.016*
H1B0.67410.88890.56260.016*
H1C0.51780.88170.51100.016*
C10.6337 (3)0.7750 (3)0.3361 (5)0.0078 (8)
H10.55590.72680.29520.009*
C1'0.7493 (3)0.6832 (3)0.3592 (6)0.0102 (8)
O1'0.8240 (3)0.6913 (3)0.5026 (4)0.0216 (8)
N20.7622 (3)0.5989 (3)0.2159 (5)0.0213 (9)
H2NA0.83510.53330.23810.026*
H2NB0.69070.59220.11590.026*
C20.6600 (4)0.8772 (3)0.1821 (5)0.0125 (9)
H20.68760.83730.05780.015*
C30.5383 (4)0.9558 (4)0.1451 (7)0.0230 (10)
H3A0.55751.01980.04850.034*
H3B0.51100.99520.26650.034*
H3C0.46900.90230.09680.034*
O40.7611 (2)0.9587 (2)0.2494 (4)0.0175 (7)
H40.83590.91580.25580.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0136 (6)0.0217 (7)0.0163 (7)0.0004 (3)0.0039 (4)0.0026 (4)
N10.0121 (16)0.0158 (15)0.0110 (15)0.0010 (13)0.0040 (13)0.0019 (15)
C10.0037 (16)0.0103 (16)0.0094 (18)0.0018 (12)0.0002 (14)0.0035 (15)
C1'0.0017 (14)0.0163 (17)0.0125 (17)0.0019 (14)0.0015 (16)0.0041 (16)
O1'0.0139 (14)0.0356 (16)0.0154 (14)0.0094 (13)0.0075 (12)0.0025 (14)
N20.0131 (16)0.0233 (16)0.0275 (19)0.0094 (13)0.0100 (16)0.0093 (16)
C20.0089 (17)0.0168 (19)0.0119 (18)0.0040 (16)0.0015 (15)0.0014 (15)
C30.015 (2)0.032 (2)0.022 (2)0.0084 (15)0.001 (2)0.010 (2)
O40.0101 (12)0.0177 (13)0.0246 (16)0.0051 (11)0.0022 (14)0.0054 (13)
Geometric parameters (Å, º) top
N1—C11.487 (4)C1'—N21.322 (5)
C1—C1'1.531 (5)C2—O41.415 (4)
C1—C21.523 (5)C2—C31.511 (5)
C1'—O1'1.233 (4)
N1—C1—C1'107.9 (3)N2—C1'—C1115.4 (3)
N1—C1—C2110.6 (3)O4—C2—C3108.2 (3)
C1'—C1—C2112.6 (3)O4—C2—C1109.9 (3)
O1'—C1'—N2124.0 (3)C3—C2—C1111.0 (3)
O1'—C1'—C1120.6 (3)
(serNH2) top
Crystal data top
C3H9N2O2+·ClF(000) = 148
Mr = 140.57Dx = 1.450 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2y1Cell parameters from 25 reflections
a = 7.562 (2) Åθ = 0.3–67.4°
b = 4.9986 (18) ŵ = 4.64 mm1
c = 8.519 (3) ÅT = 293 K
β = 90.76 (3)°Plate, colourless
V = 322.00 (18) Å30.8 × 0.2 × 0.05 mm
Z = 2
Data collection top
Rigaku AFC5R
diffractometer
626 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.050
Graphite monochromatorθmax = 67.4°, θmin = 5.2°
ω–2θ scansh = 09
Absorption correction: ψ-scan
North, et al., 1990
k = 05
Tmin = 0.464, Tmax = 0.793l = 1010
687 measured reflections3 standard reflections every 100 reflections
638 independent reflections intensity decay: 2%
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)] = 0.050 w = 1/[\<i>w2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.162(Δ/σ)max = 0.003
S = 1.58Δρmax = 0.42 e Å3
638 reflectionsΔρmin = 0.50 e Å3
73 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2]3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.050 (14)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.01 (4)
Crystal data top
C3H9N2O2+·ClV = 322.00 (18) Å3
Mr = 140.57Z = 2
Monoclinic, P21Cu Kα radiation
a = 7.562 (2) ŵ = 4.64 mm1
b = 4.9986 (18) ÅT = 293 K
c = 8.519 (3) Å0.8 × 0.2 × 0.05 mm
β = 90.76 (3)°
Data collection top
Rigaku AFC5R
diffractometer
626 reflections with I > 2σ(I)
Absorption correction: ψ-scan
North, et al., 1990
Rint = 0.050
Tmin = 0.464, Tmax = 0.7933 standard reflections every 100 reflections
687 measured reflections intensity decay: 2%
638 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.162Δρmax = 0.42 e Å3
S = 1.58Δρmin = 0.50 e Å3
638 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
73 parametersAbsolute structure parameter: 0.01 (4)
0 restraints
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 > 2σ(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
Cl10.00171 (12)0.68380.78990 (13)0.0386 (6)
N10.7562 (4)0.6763 (11)0.1141 (4)0.0275 (9)
H1A0.83260.52680.12960.033*
H1B0.83500.82650.12350.033*
H1C0.72320.66620.02130.033*
C10.6193 (5)0.6279 (9)0.2351 (4)0.0238 (11)
H10.58030.44130.22820.029*
C1'0.4649 (6)0.8074 (10)0.1998 (4)0.0224 (10)
N20.3120 (5)0.7451 (10)0.2644 (5)0.0387 (12)
H2NA0.21110.88260.25820.046*
H2NB0.34810.70230.37090.046*
O1'0.4840 (4)1.0101 (7)0.1163 (4)0.0289 (8)
C20.6940 (6)0.6800 (14)0.4002 (4)0.0317 (10)
H2A0.61700.59780.47660.038*
H2B0.80930.59640.41010.038*
O30.7104 (5)0.9590 (9)0.4346 (3)0.0393 (10)
H30.76850.98290.54420.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0274 (7)0.0285 (8)0.0601 (8)0.0052 (5)0.0039 (4)0.0005 (5)
N10.0257 (16)0.0281 (19)0.0288 (14)0.002 (2)0.0005 (12)0.0068 (18)
C10.0233 (19)0.018 (3)0.0302 (16)0.0057 (16)0.0008 (14)0.0014 (16)
C1'0.0240 (17)0.018 (2)0.0255 (15)0.0018 (19)0.0031 (13)0.0010 (16)
N20.0234 (18)0.036 (3)0.057 (2)0.0065 (18)0.0055 (16)0.011 (2)
O1'0.0267 (15)0.0214 (17)0.0387 (13)0.0040 (14)0.0001 (12)0.0071 (14)
C20.033 (2)0.035 (2)0.0272 (17)0.005 (3)0.0036 (14)0.004 (2)
O30.0399 (17)0.045 (2)0.0329 (15)0.0029 (17)0.0013 (13)0.0116 (17)
Geometric parameters (Å, º) top
N1—C11.491 (5)C1'—O1'1.247 (6)
C1—C1'1.500 (6)C1'—N21.324 (6)
C1—C21.531 (5)C2—O31.430 (8)
N1—C1—C1'108.0 (3)O1'—C1'—C1120.3 (4)
N1—C1—C2110.9 (3)N2—C1'—C1117.2 (4)
C1'—C1—C2111.1 (4)O3—C2—C1112.6 (4)
O1'—C1'—N2122.4 (4)
(metNH2) top
Crystal data top
C5H13N2OS+·ClF(000) = 196
Mr = 184.68Dx = 1.372 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2y1Cell parameters from 25 reflections
a = 7.591 (3) Åθ = 0.3–67.5°
b = 5.029 (3) ŵ = 5.51 mm1
c = 11.786 (4) ÅT = 293 K
β = 96.49 (3)°Plate, colourless
V = 447.0 (4) Å30.7 × 0.2 × 0.05 mm
Z = 2
Data collection top
Rigaku AFC5R
diffractometer
811 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 67.5°, θmin = 3.8°
ω–2θ scansh = 99
Absorption correction: ψ-scan (north, et al., 1990)
?
k = 06
Tmin = 0.697, Tmax = 0.759l = 130
907 measured reflections3 standard reflections every 100 reflections
864 independent reflections intensity decay: 2%
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)] = 0.059H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.163 w = 1/[\<i>w2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.44(Δ/σ)max = 0.249
864 reflectionsΔρmax = 0.57 e Å3
90 parametersΔρmin = 0.52 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (5)
Crystal data top
C5H13N2OS+·ClV = 447.0 (4) Å3
Mr = 184.68Z = 2
Monoclinic, P21Cu Kα radiation
a = 7.591 (3) ŵ = 5.51 mm1
b = 5.029 (3) ÅT = 293 K
c = 11.786 (4) Å0.7 × 0.2 × 0.05 mm
β = 96.49 (3)°
Data collection top
Rigaku AFC5R
diffractometer
811 reflections with I > 2σ(I)
Absorption correction: ψ-scan (north, et al., 1990)
?
Rint = 0.023
Tmin = 0.697, Tmax = 0.7593 standard reflections every 100 reflections
907 measured reflections intensity decay: 2%
864 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.059H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.163(Δ/σ)max = 0.249
S = 1.44Δρmax = 0.57 e Å3
864 reflectionsΔρmin = 0.52 e Å3
90 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
0 restraintsAbsolute structure parameter: 0.01 (5)
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 > 2σ(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
Cl0.51904 (16)0.47300.64719 (12)0.0384 (5)
S40.8109 (2)0.4047 (5)0.97871 (12)0.0431 (5)
N10.7346 (6)0.4648 (12)1.4153 (3)0.0291 (10)
H1A0.68030.31421.40730.035*
H1B0.69300.62581.40890.035*
H1C0.77530.46241.48980.035*
C10.8676 (7)0.4039 (13)1.3348 (4)0.0292 (12)
H10.90390.21721.34270.035*
C1'1.0272 (8)0.5838 (14)1.3652 (5)0.0300 (13)
O1'1.0093 (5)0.8075 (10)1.4009 (4)0.0355 (11)
N21.1836 (6)0.4804 (14)1.3470 (5)0.0425 (13)
H2NA1.25830.55651.36010.051*
H2NB1.20610.29061.33730.051*
C20.7816 (6)0.4573 (14)1.2116 (4)0.0320 (12)
H2A0.66710.37011.19960.038*
H2B0.76300.64691.20070.038*
C30.9003 (8)0.3536 (19)1.1248 (5)0.0468 (19)
H3A0.91970.16471.13750.056*
H3B1.01450.44131.13800.056*
C50.6515 (10)0.1451 (19)0.9597 (7)0.056 (2)
H5A0.59280.15080.88320.084*
H5B0.56580.16761.01290.084*
H5C0.70970.02340.97270.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0321 (7)0.0372 (8)0.0472 (8)0.0020 (6)0.0097 (5)0.0016 (7)
S40.0492 (9)0.0507 (12)0.0317 (8)0.0083 (7)0.0154 (6)0.0003 (7)
N10.028 (2)0.031 (2)0.029 (2)0.002 (2)0.0063 (15)0.002 (2)
C10.028 (2)0.029 (3)0.031 (3)0.001 (2)0.007 (2)0.002 (3)
C1'0.026 (3)0.035 (3)0.028 (3)0.002 (3)0.000 (2)0.002 (3)
O1'0.0278 (19)0.032 (3)0.046 (2)0.0023 (18)0.0012 (17)0.010 (2)
N20.023 (2)0.039 (3)0.066 (3)0.000 (2)0.007 (2)0.013 (3)
C20.030 (2)0.038 (3)0.029 (2)0.005 (3)0.007 (2)0.001 (3)
C30.037 (3)0.070 (5)0.035 (3)0.000 (3)0.011 (2)0.010 (3)
C50.049 (4)0.060 (5)0.060 (5)0.011 (4)0.011 (3)0.014 (4)
Geometric parameters (Å, º) top
S4—C51.777 (8)C1—C21.547 (7)
S4—C31.797 (6)C1'—O1'1.214 (8)
N1—C11.494 (6)C1'—N21.335 (8)
C1—C1'1.522 (8)C2—C31.529 (8)
C5—S4—C3101.2 (4)O1'—C1'—C1121.0 (6)
N1—C1—C1'107.8 (5)N2—C1'—C1115.4 (6)
N1—C1—C2108.5 (4)C3—C2—C1110.5 (5)
C1'—C1—C2111.0 (5)C2—C3—S4113.9 (5)
O1'—C1'—N2123.5 (6)
(trpNH2) top
Crystal data top
C11H14ClN3OF(000) = 252
Mr = 239.70Dx = 1.374 Mg m3
Dm = 1.362 (5) Mg m3
Dm measured by not measured
Monoclinic, P21Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2y1Cell parameters from 25 reflections
a = 7.6394 (11) Åθ = 0.3–65.0°
b = 5.2786 (13) ŵ = 2.78 mm1
c = 14.5967 (14) ÅT = 293 K
β = 100.047 (10)°Needle, colourless
V = 579.59 (17) Å30.5 × 0.2 × 0.2 mm
Z = 2
Data collection top
Rigaku AFC5R
diffractometer
1100 independent reflections
Radiation source: fine-focus sealed tube1075 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω–2θ scansθmax = 65.0°, θmin = 3.1°
Absorption correction: ψ-scan
North, et al., 1990
h = 08
Tmin = 0.329, Tmax = 0.573k = 60
1188 measured reflectionsl = 1716
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)] = 0.030Calculated w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.095(Δ/σ)max = 0.002
S = 0.91Δρmax = 0.31 e Å3
1100 reflectionsΔρmin = 0.19 e Å3
145 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.040 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.008 (17)
Crystal data top
C11H14ClN3OV = 579.59 (17) Å3
Mr = 239.70Z = 2
Monoclinic, P21Cu Kα radiation
a = 7.6394 (11) ŵ = 2.78 mm1
b = 5.2786 (13) ÅT = 293 K
c = 14.5967 (14) Å0.5 × 0.2 × 0.2 mm
β = 100.047 (10)°
Data collection top
Rigaku AFC5R
diffractometer
1100 independent reflections
Absorption correction: ψ-scan
North, et al., 1990
1075 reflections with I > 2σ(I)
Tmin = 0.329, Tmax = 0.573Rint = 0.038
1188 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095Δρmax = 0.31 e Å3
S = 0.91Δρmin = 0.19 e Å3
1100 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
145 parametersAbsolute structure parameter: 0.008 (17)
0 restraints
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
Cl10.38566 (7)0.75010.61629 (3)0.0430 (3)
N10.3602 (2)0.2296 (5)0.59678 (12)0.0360 (5)
H1A0.33640.25080.53490.043*
H1B0.44880.10300.61680.043*
H1C0.40550.39540.62020.043*
C10.1952 (3)0.1336 (5)0.62503 (15)0.0301 (5)
H10.15000.00860.58450.036*
C1'0.0596 (3)0.3436 (5)0.61116 (16)0.0343 (6)
N20.1034 (3)0.2816 (6)0.62450 (16)0.0501 (6)
H2NA0.18840.41130.62190.060*
H2NB0.15310.11510.61910.060*
O1'0.1002 (3)0.5591 (4)0.59308 (16)0.0518 (5)
C20.2354 (3)0.0391 (5)0.72622 (15)0.0340 (5)
H2A0.12580.02100.74360.041*
H2B0.31610.10390.72960.041*
C30.3162 (3)0.2355 (6)0.79574 (13)0.0326 (5)
C40.2326 (3)0.4304 (6)0.83237 (16)0.0388 (6)
H40.11140.46430.81830.047*
C50.5008 (3)0.2535 (5)0.83688 (13)0.0312 (5)
N60.3539 (3)0.5688 (5)0.89292 (13)0.0421 (6)
H60.31790.72980.92170.051*
C70.5179 (3)0.4649 (5)0.89691 (14)0.0359 (5)
C80.6511 (3)0.1112 (5)0.82866 (15)0.0377 (6)
H80.64200.03010.79010.045*
C90.6831 (3)0.5369 (6)0.94831 (15)0.0435 (6)
H90.69360.67560.98820.052*
C100.8127 (3)0.1832 (7)0.87855 (16)0.0447 (7)
H100.91370.08990.87320.054*
C110.8283 (3)0.3947 (7)0.93743 (17)0.0476 (7)
H110.93980.43970.96990.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0474 (4)0.0413 (4)0.0417 (4)0.0092 (3)0.0119 (2)0.0044 (3)
N10.0400 (9)0.0348 (12)0.0351 (9)0.0046 (10)0.0118 (7)0.0025 (10)
C10.0330 (12)0.0266 (11)0.0301 (10)0.0006 (9)0.0038 (7)0.0010 (9)
C1'0.0388 (13)0.0300 (12)0.0326 (11)0.0012 (11)0.0021 (8)0.0013 (10)
N20.0321 (10)0.0441 (14)0.0740 (15)0.0017 (11)0.0086 (9)0.0046 (13)
O1'0.0494 (10)0.0293 (10)0.0774 (13)0.0031 (9)0.0128 (9)0.0112 (10)
C20.0375 (10)0.0299 (11)0.0343 (10)0.0021 (10)0.0055 (8)0.0041 (10)
C30.0382 (10)0.0331 (12)0.0271 (10)0.0012 (11)0.0077 (8)0.0045 (11)
C40.0440 (11)0.0392 (14)0.0340 (11)0.0060 (11)0.0094 (9)0.0021 (11)
C50.0400 (10)0.0301 (11)0.0238 (9)0.0013 (12)0.0065 (7)0.0046 (10)
N60.0590 (12)0.0351 (12)0.0337 (10)0.0039 (11)0.0123 (9)0.0046 (9)
C70.0495 (12)0.0327 (13)0.0265 (10)0.0018 (11)0.0092 (8)0.0005 (10)
C80.0428 (12)0.0390 (13)0.0313 (11)0.0003 (11)0.0067 (8)0.0021 (10)
C90.0614 (15)0.0406 (14)0.0276 (10)0.0154 (14)0.0056 (10)0.0022 (11)
C100.0389 (12)0.0563 (19)0.0381 (12)0.0010 (13)0.0049 (9)0.0011 (13)
C110.0452 (12)0.0589 (18)0.0361 (11)0.0143 (14)0.0002 (10)0.0010 (13)
Geometric parameters (Å, º) top
N1—C11.483 (3)C4—N61.374 (3)
C1—C1'1.507 (3)C5—C81.395 (4)
C1—C21.538 (3)C5—C71.410 (4)
C1'—O1'1.220 (4)N6—C71.360 (3)
C1'—N21.334 (3)C7—C91.403 (3)
C2—C31.506 (3)C8—C101.373 (3)
C3—C41.368 (4)C9—C111.371 (4)
C3—C51.436 (3)C10—C111.401 (4)
C1'—C1—N1108.0 (2)C8—C5—C7119.4 (2)
C1'—C1—C2112.66 (19)C8—C5—C3133.7 (2)
N1—C1—C2109.91 (17)C7—C5—C3106.9 (2)
O1'—C1'—N2122.6 (3)C7—N6—C4109.0 (2)
O1'—C1'—C1121.4 (2)N6—C7—C5107.93 (19)
N2—C1'—C1115.9 (2)N6—C7—C9130.5 (3)
C3—C2—C1114.4 (2)C5—C7—C9121.6 (2)
C4—C3—C5106.1 (2)C10—C8—C5118.9 (2)
C4—C3—C2128.1 (2)C11—C9—C7117.4 (3)
C5—C3—C2125.7 (2)C8—C10—C11121.2 (2)
C3—C4—N6110.1 (2)C9—C11—C10121.5 (2)
(glnNH2) top
Crystal data top
C5H12N3O2+·ClF(000) = 192
Mr = 181.63Dx = 1.477 Mg m3
Dm = 1.462 (5) Mg m3
Dm measured by measured
Monoclinic, P21Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2y1Cell parameters from 25 reflections
a = 7.741 (2) Åθ = 0–67.6°
b = 4.8907 (13) ŵ = 3.83 mm1
c = 10.8159 (10) ÅT = 293 K
β = 94.180 (13)°Needle, colourless
V = 408.39 (16) Å30.8 × 0.2 × 0.2 mm
Z = 2
Data collection top
Rigaku AFC5R
diffractometer
812 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.065
Graphite monochromatorθmax = 67.6°, θmin = 4.1°
ω–2θ scansh = 09
Absorption correction: ψ-scan
North, et al., 1990
k = 05
Tmin = 0.355, Tmax = 0.465l = 1212
877 measured reflections3 standard reflections every 100 reflections
816 independent reflections intensity decay: 2%
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)] = 0.043Calculated w = 1/[\<i>w2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.137(Δ/σ)max = 0.091
S = 1.39Δρmax = 0.66 e Å3
816 reflectionsΔρmin = 0.39 e Å3
100 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2]3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.187 (19)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.00 (3)
Crystal data top
C5H12N3O2+·ClV = 408.39 (16) Å3
Mr = 181.63Z = 2
Monoclinic, P21Cu Kα radiation
a = 7.741 (2) ŵ = 3.83 mm1
b = 4.8907 (13) ÅT = 293 K
c = 10.8159 (10) Å0.8 × 0.2 × 0.2 mm
β = 94.180 (13)°
Data collection top
Rigaku AFC5R
diffractometer
812 reflections with I > 2σ(I)
Absorption correction: ψ-scan
North, et al., 1990
Rint = 0.065
Tmin = 0.355, Tmax = 0.4653 standard reflections every 100 reflections
877 measured reflections intensity decay: 2%
816 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137Δρmax = 0.66 e Å3
S = 1.39Δρmin = 0.39 e Å3
816 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
100 parametersAbsolute structure parameter: 0.00 (3)
0 restraints
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 > 2σ(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
Cl10.02342 (8)0.93750.14451 (6)0.0283 (4)
N10.7251 (3)0.9419 (9)0.8927 (2)0.0243 (7)
H1A0.80621.05700.88200.029*
H1B0.78340.79400.88310.029*
H1C0.66680.94670.95990.029*
C10.5705 (4)0.9710 (9)0.8019 (3)0.0220 (8)
H10.53851.16420.79260.026*
C1'0.4228 (4)0.8108 (9)0.8536 (3)0.0221 (7)
O1'0.4478 (3)0.5815 (7)0.8956 (2)0.0288 (7)
N20.2716 (3)0.9408 (11)0.8498 (3)0.0350 (8)
H2NA0.16450.86150.86740.042*
H2NB0.25751.09240.79860.042*
C20.6081 (4)0.8499 (10)0.6755 (2)0.0278 (9)
H2A0.65180.66520.68720.033*
H2B0.50110.84050.62310.033*
C30.7399 (5)1.0201 (9)0.6108 (3)0.0356 (10)
H3A0.69711.20580.60090.043*
H3B0.84741.02640.66270.043*
C40.7760 (4)0.9076 (12)0.4850 (3)0.0299 (10)
O50.7516 (5)0.6670 (9)0.4566 (3)0.0523 (10)
N60.8393 (4)1.0866 (9)0.4092 (3)0.0364 (9)
H6A0.86830.98940.33620.044*
H6B0.89741.24510.45750.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0253 (5)0.0304 (6)0.0297 (5)0.0029 (4)0.0045 (3)0.0013 (4)
N10.0216 (12)0.0287 (16)0.0231 (11)0.0025 (17)0.0051 (9)0.0046 (17)
C10.0243 (14)0.019 (2)0.0230 (13)0.0006 (16)0.0041 (11)0.0000 (16)
C1'0.0242 (15)0.0258 (19)0.0167 (12)0.0013 (16)0.0032 (9)0.0008 (15)
O1'0.0280 (13)0.0277 (16)0.0317 (13)0.0003 (12)0.0077 (10)0.0078 (12)
N20.0228 (13)0.039 (2)0.0438 (16)0.0054 (19)0.0035 (11)0.010 (2)
C20.0284 (16)0.035 (2)0.0206 (15)0.0079 (15)0.0061 (12)0.0004 (17)
C30.048 (2)0.036 (3)0.0244 (15)0.0107 (19)0.0146 (14)0.0065 (17)
C40.0291 (16)0.038 (3)0.0229 (17)0.0002 (17)0.0018 (12)0.006 (2)
O50.079 (2)0.038 (2)0.0423 (16)0.0132 (19)0.0202 (15)0.0157 (17)
N60.0504 (19)0.037 (2)0.0235 (14)0.0023 (19)0.0151 (13)0.0014 (16)
Geometric parameters (Å, º) top
N1—C11.499 (4)C2—C31.526 (5)
C1—C1'1.525 (5)C3—C41.512 (5)
C1—C21.538 (4)C4—O51.227 (8)
C1'—O1'1.220 (5)C4—N61.317 (6)
C1'—N21.330 (5)
N1—C1—C1'107.2 (3)C3—C2—C1112.0 (3)
N1—C1—C2110.6 (3)C4—C3—C2112.8 (3)
C1'—C1—C2108.9 (3)O5—C4—N6122.6 (4)
O1'—C1'—N2124.5 (4)O5—C4—C3122.6 (4)
O1'—C1'—C1120.4 (3)N6—C4—C3114.8 (4)
N2—C1'—C1115.1 (4)
(argNH2) top
Crystal data top
C6H19N5O22+·2ClDx = 1.358 Mg m3
Dm = 1.366 (5) Mg m3
Dm measured by measured
Mr = 264.16Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 7.536 (3) Åθ = 0.3–67.6°
b = 32.487 (3) ŵ = 4.49 mm1
c = 5.277 (4) ÅT = 293 K
V = 1291.9 (10) Å3Plate, colourless
Z = 40.5 × 0.25 × 0.1 mm
F(000) = 560
Data collection top
Rigaku AFC5R
diffractometer
1325 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 67.6°
ω–2θ scansh = 80
Absorption correction: ψ-scan
North, et al., 1990
k = 038
Tmin = 0.288, Tmax = 0.998l = 06
1364 measured reflections3 standard reflections every 100 reflections
1364 independent reflections intensity decay: 2%
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)] = 0.055Calculated w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.172(Δ/σ)max = 0.177
S = 1.64Δρmax = 0.47 e Å3
1364 reflectionsΔρmin = 0.35 e Å3
137 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.016 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.03 (4)
Crystal data top
C6H19N5O22+·2ClV = 1291.9 (10) Å3
Mr = 264.16Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 7.536 (3) ŵ = 4.49 mm1
b = 32.487 (3) ÅT = 293 K
c = 5.277 (4) Å0.5 × 0.25 × 0.1 mm
Data collection top
Rigaku AFC5R
diffractometer
1325 reflections with I > 2σ(I)
Absorption correction: ψ-scan
North, et al., 1990
Rint = 0.000
Tmin = 0.288, Tmax = 0.9983 standard reflections every 100 reflections
1364 measured reflections intensity decay: 2%
1364 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.055H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.172(Δ/σ)max = 0.177
S = 1.64Δρmax = 0.47 e Å3
1364 reflectionsΔρmin = 0.35 e Å3
137 parametersAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
0 restraintsAbsolute structure parameter: 0.03 (4)
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 > 2σ(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
N10.0000 (5)0.96691 (8)1.2482 (7)0.0351 (8)
H1A0.06840.95931.09640.042*
H1B0.06970.96061.37360.042*
H1C0.04740.99251.23970.042*
C10.1574 (5)0.94187 (11)1.3143 (7)0.0331 (9)
H10.20800.95311.47080.040*
C1'0.2943 (6)0.94782 (10)1.1029 (8)0.0349 (9)
O1'0.2594 (4)0.96764 (8)0.9123 (6)0.0392 (7)
N20.4494 (6)0.93005 (15)1.1393 (11)0.0712 (15)
H2NA0.45790.91411.24270.085*
H2NB0.51580.93350.97290.085*
C20.1111 (5)0.89690 (10)1.3626 (9)0.0332 (9)
H2A0.21560.88311.42850.040*
H2B0.02050.89581.49310.040*
C30.0450 (6)0.87301 (10)1.1332 (9)0.0395 (10)
H3A0.06710.88441.07620.047*
H3B0.12990.87540.99580.047*
C40.0210 (6)0.82801 (10)1.2035 (10)0.0415 (10)
H4A0.13280.81731.26630.050*
H4B0.06540.82591.33910.050*
N50.0375 (5)0.80304 (9)0.9913 (9)0.0431 (10)
H50.04780.79750.84570.052*
C60.2067 (6)0.79688 (11)0.9338 (9)0.0373 (9)
N70.3361 (4)0.81292 (11)1.0647 (8)0.0457 (10)
H7A0.43500.80720.99110.055*
H7B0.33250.82571.18280.055*
N80.2479 (6)0.77385 (12)0.7298 (8)0.0523 (10)
H8A0.16760.75130.70920.063*
H8B0.38840.77290.69310.063*
O1W0.5968 (6)0.86819 (10)0.4949 (8)0.0607 (10)
Cl10.76135 (13)0.94887 (3)0.7367 (2)0.0422 (4)
Cl20.33399 (13)0.79542 (3)0.6922 (2)0.0489 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0408 (16)0.0297 (13)0.0348 (16)0.0004 (13)0.0078 (17)0.0006 (13)
C10.039 (2)0.0278 (15)0.0327 (19)0.0059 (14)0.003 (2)0.0005 (15)
C1'0.043 (2)0.0257 (16)0.0355 (18)0.0027 (15)0.002 (2)0.0049 (16)
O1'0.0432 (15)0.0398 (13)0.0345 (15)0.0041 (11)0.0059 (14)0.0063 (12)
N1'0.047 (2)0.096 (3)0.071 (3)0.017 (2)0.018 (2)0.051 (3)
C20.0386 (19)0.0278 (16)0.0332 (19)0.0041 (16)0.0033 (17)0.0070 (15)
C30.048 (2)0.0272 (17)0.044 (2)0.0015 (16)0.002 (2)0.0035 (17)
C40.0404 (18)0.0282 (17)0.056 (3)0.0023 (15)0.008 (2)0.0043 (18)
N50.0379 (17)0.0293 (15)0.062 (2)0.0024 (12)0.004 (2)0.0052 (17)
C60.044 (2)0.0235 (15)0.044 (2)0.0010 (16)0.003 (2)0.0013 (16)
N70.0373 (17)0.055 (2)0.045 (2)0.0019 (16)0.002 (2)0.0170 (19)
N80.063 (2)0.0407 (18)0.053 (2)0.0025 (17)0.006 (3)0.0142 (17)
O1W0.080 (2)0.0467 (15)0.055 (2)0.0018 (16)0.002 (2)0.0040 (17)
Cl10.0431 (6)0.0423 (6)0.0412 (6)0.0008 (4)0.0088 (5)0.0000 (4)
Cl20.0408 (6)0.0501 (6)0.0557 (8)0.0022 (4)0.0074 (5)0.0077 (5)
Geometric parameters (Å, º) top
N1—C11.480 (5)C3—C41.519 (5)
C1—C21.524 (4)C4—N51.451 (6)
C1—C1'1.532 (6)N5—C61.326 (6)
C1'—O1'1.222 (5)C6—N71.304 (6)
C1'—N21.317 (6)C6—N81.347 (6)
C2—C31.522 (6)
N1—C1—C2112.5 (3)C4—C3—C2109.6 (4)
N1—C1—C1'107.4 (3)N5—C4—C3112.7 (4)
C2—C1—C1'113.4 (3)C6—N5—C4123.6 (4)
O1'—C1'—N2122.8 (4)N7—C6—N5122.5 (4)
O1'—C1'—C1121.4 (4)N7—C6—N8118.3 (4)
N2—C1'—C1115.8 (4)N5—C6—N8119.2 (4)
C3—C2—C1115.5 (3)

Experimental details

(ileNH2)(valNH2)(thrNH2)(serNH2)
Crystal data
Chemical formulaC6H15N2O+·ClC5H13N2O+·ClC4H11N2O2+·ClC3H9N2O2+·Cl
Mr166.65152.62154.60140.57
Crystal system, space groupMonoclinic, P21Monoclinic, P21Orthorhombic, P212121Monoclinic, P21
Temperature (K)293293293293
a, b, c (Å)7.5775 (13), 4.8971 (13), 12.5686 (14)5.3377 (8), 7.4572 (9), 9.899 (1)10.1624 (15), 10.5673 (17), 6.749 (3)7.562 (2), 4.9986 (18), 8.519 (3)
α, β, γ (°)90, 94.195 (12), 9090, 91.73 (1), 9090, 90, 9090, 90.76 (3), 90
V3)465.14 (16)393.84 (9)724.8 (3)322.00 (18)
Z2242
Radiation typeCu KαCu KαCu KαCu Kα
µ (mm1)3.203.734.174.64
Crystal size (mm)0.6 × 0.4 × 0.050.8 × 0.6 × 0.30.8 × 0.6 × 0.60.8 × 0.2 × 0.05
Data collection
DiffractometerRigaku AFC5R
diffractometer
Rigaku AFC5R
diffractometer
Rigaku AFC5R
diffractometer
Rigaku AFC5R
diffractometer
Absorption correctionψ-scan
North, et al., 1990
ψ-scan
North, et al., 1990
ψ-scan
North, et al., 1990
Tmin, Tmax0.629, 0.9990.782, 0.9990.464, 0.793
No. of measured, independent and
observed [I > 2σ(I)] reflections
963, 893, 817 1458, 731, 718 710, 710, 710 687, 638, 626
Rint0.0520.1350.0000.050
(sin θ/λ)max1)0.5880.5880.5780.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.069, 0.187, 1.66 0.037, 0.097, 0.75 0.047, 0.121, 1.10 0.050, 0.162, 1.58
No. of reflections893731710638
No. of parameters90828373
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
(Δ/σ)max0.0940.1760.0490.003
Δρmax, Δρmin (e Å3)0.70, 0.290.30, 0.410.50, 0.590.42, 0.50
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter0.04 (5)0.009 (16)0.06 (3)0.01 (4)


(metNH2)(trpNH2)(glnNH2)(argNH2)
Crystal data
Chemical formulaC5H13N2OS+·ClC11H14ClN3OC5H12N3O2+·ClC6H19N5O22+·2Cl
Mr184.68239.70181.63264.16
Crystal system, space groupMonoclinic, P21Monoclinic, P21Monoclinic, P21Orthorhombic, P212121
Temperature (K)293293293293
a, b, c (Å)7.591 (3), 5.029 (3), 11.786 (4)7.6394 (11), 5.2786 (13), 14.5967 (14)7.741 (2), 4.8907 (13), 10.8159 (10)7.536 (3), 32.487 (3), 5.277 (4)
α, β, γ (°)90, 96.49 (3), 9090, 100.047 (10), 9090, 94.180 (13), 9090, 90, 90
V3)447.0 (4)579.59 (17)408.39 (16)1291.9 (10)
Z2224
Radiation typeCu KαCu KαCu KαCu Kα
µ (mm1)5.512.783.834.49
Crystal size (mm)0.7 × 0.2 × 0.050.5 × 0.2 × 0.20.8 × 0.2 × 0.20.5 × 0.25 × 0.1
Data collection
DiffractometerRigaku AFC5R
diffractometer
Rigaku AFC5R
diffractometer
Rigaku AFC5R
diffractometer
Rigaku AFC5R
diffractometer
Absorption correctionψ-scan (North, et al., 1990)ψ-scan
North, et al., 1990
ψ-scan
North, et al., 1990
ψ-scan
North, et al., 1990
Tmin, Tmax0.697, 0.7590.329, 0.5730.355, 0.4650.288, 0.998
No. of measured, independent and
observed [I > 2σ(I)] reflections
907, 864, 811 1188, 1100, 1075 877, 816, 812 1364, 1364, 1325
Rint0.0230.0380.0650.000
(sin θ/λ)max1)0.5990.5880.6000.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.163, 1.44 0.030, 0.095, 0.91 0.043, 0.137, 1.39 0.055, 0.172, 1.64
No. of reflections86411008161364
No. of parameters90145100137
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
(Δ/σ)max0.2490.0020.0910.177
Δρmax, Δρmin (e Å3)0.57, 0.520.31, 0.190.66, 0.390.47, 0.35
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter0.01 (5)0.008 (17)0.00 (3)0.03 (4)

Computer programs: MSC/AFC (Molecular Structure Corp. 1991), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997).

 

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