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Racemates of hydro­phobic amino acids with linear side chains are known to undergo a unique series of solid-state phase transitions that involve sliding of mol­ecular bilayers upon heating or cooling. Recently, this behaviour was shown to extend also to quasiracemates of two different amino acids with opposite handedness [Görbitz & Karen (2015). J. Phys. Chem. B, 119, 4975-4984]. Previous investigations are here extended to an L-2-amino­butyric acid-D-me­thio­nine (1/1) co-crystal, C4H9NO2·C5H11NO2S. The significant difference in size between the -CH2CH3 and -CH2CH2SCH3 side chains leads to extensive disorder at room temperature, which is essentially resolved after a phase transition at 229 K to an unprecedented triclinic form where all four D-me­thio­­nine mol­ecules in the asymmetric unit have different side-chain conformations and all three side-chain rotamers are used for the four partner L-2-amino­butyric acid mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616008858/sk3626sup1.cif
Contains datablocks global, 103, 293

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616008858/sk3626103sup2.hkl
Contains datablock 103

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616008858/sk3626293sup3.hkl
Contains datablock 293

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616008858/sk3626103sup4.cml
Supplementary material

CCDC references: 1483016; 1483015

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2014); cell refinement: APEX2 (Bruker, 2014); data reduction: APEX2 (Bruker, 2014); program(s) used to solve structure: APEX2 (Bruker, 2014); program(s) used to refine structure: SHELXT (Sheldrick, 2015a); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

(103) (S)-2-Aminobutanoic acid–(R)-2-amino-4-(methylsulfanyl)butanoic acid (1/1) top
Crystal data top
C4H9NO2·C5H11NO2SZ = 4
Mr = 252.33F(000) = 544
Triclinic, P1Dx = 1.295 Mg m3
a = 9.4890 (15) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.8774 (15) ÅCell parameters from 6485 reflections
c = 15.079 (2) Åθ = 3.0–50.1°
α = 71.429 (4)°µ = 0.25 mm1
β = 75.650 (4)°T = 103 K
γ = 89.369 (4)°Plate, colorless
V = 1294.4 (4) Å30.69 × 0.65 × 0.10 mm
Data collection top
Bruker D8 Venture with Photon 100 CMOS detector
diffractometer
4175 independent reflections
Radiation source: fine-focus sealed tube3442 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
Detector resolution: 8.3 pixels mm-1θmax = 25.2°, θmin = 2.2°
Sets of exposures each taken over 0.5° ω rotation scansh = 1011
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
k = 1011
Tmin = 0.888, Tmax = 1.000l = 018
4175 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.072 w = 1/[σ2(Fo2) + (0.1022P)2 + 1.242P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.186(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.43 e Å3
4175 reflectionsΔρmin = 0.45 e Å3
628 parametersAbsolute structure: No quotients, so Flack parameter determined by classical intensity fit
461 restraintsAbsolute structure parameter: 0.18 (12)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The final refinement was done against the HKLF 5 type file for twin component 1 with intensities corrected for overlap with component 2.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1E0.4882 (8)0.7762 (9)0.4273 (6)0.0217 (15)
O2E0.6454 (9)0.9697 (9)0.3503 (6)0.0254 (16)
N1E0.6829 (10)0.5925 (10)0.3894 (6)0.0187 (18)
H1E0.60250.56050.37710.028*
H2E0.66370.58390.45320.028*
H3E0.75870.53960.37440.028*
C1E0.6080 (12)0.8369 (12)0.3740 (8)0.022 (2)
C21E0.722 (4)0.746 (5)0.3294 (12)0.016 (3)0.650 (19)
H21E0.82320.77650.32700.020*0.650 (19)
C31E0.706 (2)0.7613 (18)0.2269 (11)0.018 (4)0.650 (19)
H31E0.77290.69870.19960.022*0.650 (19)
H32E0.60510.72940.23170.022*0.650 (19)
C41E0.7402 (17)0.9146 (16)0.1596 (11)0.024 (4)0.650 (19)
H41E0.75940.91630.09240.036*0.650 (19)
H42E0.82650.95590.16920.036*0.650 (19)
H43E0.65690.97080.17380.036*0.650 (19)
C22E0.709 (7)0.746 (8)0.3413 (19)0.016 (3)0.350 (19)
H22E0.79950.77040.35790.020*0.350 (19)
C32E0.760 (3)0.776 (4)0.2306 (18)0.018 (4)0.350 (19)
H33E0.81650.87010.19950.022*0.350 (19)
H34E0.82470.70180.21730.022*0.350 (19)
C42E0.632 (3)0.776 (3)0.187 (2)0.032 (9)0.350 (19)
H44E0.66790.79100.11790.049*0.350 (19)
H45E0.57080.85400.19660.049*0.350 (19)
H46E0.57380.68450.21930.049*0.350 (19)
O1G0.0238 (8)0.7764 (9)0.4295 (5)0.0199 (15)
O2G0.1385 (9)0.9672 (9)0.3650 (6)0.0241 (16)
N1G0.1730 (10)0.5925 (10)0.3956 (6)0.0169 (17)
H1G0.09270.57440.37720.025*
H2G0.15050.56920.46120.025*
H3G0.24570.53940.37610.025*
C1G0.0984 (11)0.8378 (12)0.3845 (8)0.016 (2)
C21G0.223 (3)0.749 (3)0.3497 (10)0.013 (3)0.655 (16)
H21G0.30820.76730.37290.015*0.655 (16)
C31G0.2710 (16)0.7912 (18)0.2389 (10)0.020 (3)0.655 (16)
H31G0.33710.72000.22170.024*0.655 (16)
H32G0.32800.88500.21300.024*0.655 (16)
C41G0.1474 (18)0.801 (2)0.1884 (12)0.038 (5)0.655 (16)
H41G0.18910.82050.11890.057*0.655 (16)
H42G0.08760.87950.19830.057*0.655 (16)
H43G0.08670.71090.21570.057*0.655 (16)
C22G0.204 (6)0.742 (5)0.3380 (16)0.013 (3)0.345 (16)
H22G0.30590.77020.33610.015*0.345 (16)
C32G0.198 (4)0.763 (2)0.2337 (17)0.020 (3)0.345 (16)
H33G0.09820.73220.23510.024*0.345 (16)
H34G0.26570.69960.20810.024*0.345 (16)
C42G0.236 (4)0.917 (3)0.163 (2)0.041*0.345 (16)
H44G0.25520.91580.09650.062*0.345 (16)
H45G0.32300.95740.17240.062*0.345 (16)
H46G0.15410.97530.17580.062*0.345 (16)
O1B0.7309 (8)0.0760 (9)0.5794 (5)0.0193 (15)
O2B0.5663 (9)0.1107 (9)0.6611 (5)0.0206 (15)
N1B0.5415 (10)0.2694 (10)0.6085 (6)0.0180 (18)
H1B0.56100.27270.54560.027*
H2B0.62070.30720.61880.027*
H3B0.46360.32090.62170.027*
C1B0.6101 (11)0.0203 (11)0.6330 (7)0.015 (2)
C21B0.5069 (18)0.1143 (18)0.6746 (9)0.012 (3)0.832 (16)
H21B0.40330.08210.68340.015*0.832 (16)
C31B0.5322 (14)0.1196 (13)0.7718 (9)0.022 (3)0.832 (16)
H31B0.63690.14470.76210.026*0.832 (16)
H32B0.47620.19570.79040.026*0.832 (16)
C41B0.4870 (15)0.0208 (14)0.8529 (9)0.028 (3)0.832 (16)
H41B0.52040.10000.82780.034*0.832 (16)
H42B0.37920.03230.87480.034*0.832 (16)
S11B0.5587 (10)0.0350 (10)0.9551 (6)0.0320 (13)0.832 (16)
C22B0.496 (7)0.142 (10)0.672 (3)0.012 (3)0.168 (16)
H22B0.40090.12080.66060.015*0.168 (16)
C32B0.471 (4)0.072 (6)0.784 (2)0.022 (3)0.168 (16)
H33B0.41000.13240.81710.026*0.168 (16)
H34B0.41620.02270.80470.026*0.168 (16)
C42B0.611 (3)0.052 (7)0.815 (2)0.028*0.168 (16)
H43B0.67210.14380.78540.034*0.168 (16)
H44B0.66530.01960.78890.034*0.168 (16)
S12B0.586 (4)0.006 (4)0.944 (2)0.0320 (13)0.168 (16)
C5B0.4806 (19)0.1149 (18)0.9896 (12)0.070 (4)
H51B0.54210.20290.94990.105*
H52B0.47520.09811.05810.105*
H53B0.38240.12490.97950.105*
O1C0.1618 (9)0.5833 (9)0.5859 (5)0.0187 (15)
O2C0.2785 (9)0.3947 (9)0.6496 (5)0.0218 (15)
N1C0.3431 (10)0.7672 (10)0.6111 (6)0.0172 (18)
H1C0.37860.77490.54770.026*
H2C0.40450.81840.62830.026*
H3C0.25330.80200.61990.026*
C1C0.2529 (11)0.5241 (11)0.6314 (7)0.017 (2)
C21C0.3315 (12)0.6130 (11)0.6725 (7)0.016 (2)0.936 (19)
H21C0.43180.58020.67140.019*0.936 (19)
C31C0.2519 (14)0.6019 (17)0.7758 (8)0.025 (3)0.936 (19)
H31C0.30240.66980.79590.029*0.936 (19)
H32C0.15180.63190.77670.029*0.936 (19)
C41C0.2423 (17)0.4538 (14)0.8491 (9)0.046 (4)0.936 (19)
H41C0.17280.39060.83950.069*0.936 (19)
H42C0.20930.45950.91470.069*0.936 (19)
H43C0.33860.41540.84060.069*0.936 (19)
C22C0.3315 (12)0.6130 (11)0.6725 (7)0.016 (2)0.064 (19)
H22C0.43420.58510.65840.019*0.064 (19)
C32C0.295 (7)0.60 (2)0.780 (3)0.025 (3)0.064 (19)
H33C0.35250.52010.81160.029*0.064 (19)
H34C0.32690.68670.78680.029*0.064 (19)
C42C0.135 (8)0.56 (2)0.832 (4)0.043*0.064 (19)
H44C0.11670.57680.89440.065*0.064 (19)
H45C0.11030.45840.84330.065*0.064 (19)
H46C0.07600.61960.79260.065*0.064 (19)
O1A0.6717 (9)0.5869 (9)0.5775 (5)0.0223 (16)
O2A0.7779 (9)0.3929 (9)0.6481 (6)0.0253 (17)
N1A0.8362 (10)0.7636 (10)0.6190 (6)0.0182 (18)
H1A0.87810.77300.55590.027*
H2A0.89330.81320.64020.027*
H3A0.74660.79860.62440.027*
C1A0.7533 (11)0.5238 (11)0.6283 (7)0.015 (2)
C2A0.8209 (12)0.6072 (11)0.6795 (7)0.015 (2)
H21A0.91960.57370.68380.018*
C3A0.7253 (12)0.5865 (12)0.7813 (7)0.020 (2)
H31A0.62770.61870.77590.025*
H32A0.71270.48280.81830.025*
C4A0.7816 (14)0.6632 (14)0.8375 (8)0.033 (3)
H41A0.86330.61430.85930.050*
H42A0.70360.66380.89380.050*
H43A0.81480.76190.79620.050*
O1D0.2394 (8)0.0842 (9)0.5821 (5)0.0199 (15)
O2D0.0771 (9)0.1056 (9)0.6484 (6)0.0235 (16)
N1D0.0419 (10)0.2701 (10)0.6116 (6)0.0174 (18)
H1D0.12660.29350.62310.026*
H2D0.02950.32300.63320.026*
H3D0.05490.28870.54690.026*
C1D0.1136 (11)0.0239 (11)0.6276 (7)0.017 (2)
C2D0.0015 (11)0.1146 (11)0.6635 (7)0.015 (2)
H21D0.09390.09120.64910.018*
C3D0.0319 (12)0.0811 (12)0.7747 (8)0.023 (2)
H3D10.09170.15530.79320.028*
H3D20.08950.01220.80780.028*
C4D0.1018 (12)0.0757 (12)0.8090 (7)0.018 (2)
H41D0.15630.17090.77920.021*
H42D0.16450.00590.78690.021*
S1D0.0656 (6)0.0256 (7)0.9401 (3)0.0325 (7)
C5D0.0043 (15)0.1595 (13)0.9737 (9)0.045 (3)
H51D0.01630.20351.04420.067*
H52D0.08040.20950.94230.067*
H53D0.08460.16660.95300.067*
O1F1.0361 (8)0.2797 (9)0.4270 (5)0.0188 (15)
O2F0.9497 (9)0.4753 (9)0.3402 (5)0.0191 (15)
N1F0.8716 (10)0.0993 (10)0.3897 (6)0.0204 (19)
H1F0.82020.04520.36780.031*
H2F0.82230.09550.45050.031*
H3F0.96070.06470.39070.031*
C1F0.9638 (11)0.3423 (12)0.3695 (7)0.014 (2)
C2F0.8907 (11)0.2522 (11)0.3233 (7)0.014 (2)
H21F0.79350.28780.31680.017*
C3F0.9860 (13)0.2558 (12)0.2243 (7)0.025 (2)
H31F0.94760.17990.20480.030*
H32F1.08640.23500.22960.030*
C4F0.9907 (12)0.4011 (13)0.1457 (8)0.030 (2)
H41F1.06810.40300.08750.036*
H42F1.01920.47700.16910.036*
S1F0.8245 (6)0.4444 (7)0.1104 (3)0.0323 (7)
C5F0.8195 (14)0.3254 (15)0.0423 (10)0.043 (3)
H51F0.73140.33770.01850.065*
H52F0.81840.22610.08400.065*
H53F0.90590.34740.01280.065*
O1H0.5591 (9)0.2715 (9)0.4217 (5)0.0199 (15)
O2H0.4370 (9)0.4621 (9)0.3640 (5)0.0199 (15)
N1H0.3774 (10)0.0867 (10)0.3991 (6)0.0181 (18)
H1H0.31230.03460.38540.027*
H2H0.35450.07120.46400.027*
H3H0.46890.05960.37980.027*
C1H0.4635 (12)0.3306 (12)0.3809 (7)0.015 (2)
C2H0.3720 (12)0.2416 (12)0.3469 (7)0.016 (2)
H21H0.26850.26670.36340.020*
C3H0.4209 (12)0.2687 (11)0.2378 (7)0.018 (2)
H31H0.52680.25690.21920.022*
H32H0.36960.19620.22200.022*
C4H0.3910 (13)0.4173 (12)0.1788 (7)0.021 (2)
H41H0.45780.48970.18320.025*
H42H0.28960.43710.20560.025*
S1H0.4164 (6)0.4304 (7)0.0537 (3)0.0288 (6)
C5H0.3796 (15)0.6137 (14)0.0066 (9)0.044 (3)
H51H0.44090.67380.02500.066*
H52H0.27660.62510.03310.066*
H53H0.40120.64270.06410.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1E0.016 (4)0.017 (4)0.033 (4)0.001 (3)0.004 (3)0.011 (3)
O2E0.026 (4)0.013 (4)0.038 (4)0.006 (3)0.010 (3)0.008 (3)
N1E0.018 (4)0.013 (4)0.026 (4)0.005 (3)0.008 (3)0.005 (3)
C1E0.020 (5)0.020 (5)0.027 (5)0.007 (4)0.007 (4)0.006 (4)
C21E0.015 (5)0.012 (4)0.019 (4)0.005 (4)0.002 (4)0.003 (4)
C31E0.014 (6)0.018 (5)0.023 (4)0.002 (5)0.004 (4)0.008 (4)
C41E0.025 (8)0.018 (8)0.021 (7)0.005 (6)0.005 (6)0.003 (6)
C22E0.015 (5)0.012 (4)0.019 (4)0.005 (4)0.002 (4)0.003 (4)
C32E0.014 (6)0.018 (5)0.023 (4)0.002 (5)0.004 (4)0.008 (4)
C42E0.028 (13)0.028 (13)0.037 (13)0.003 (10)0.005 (10)0.014 (10)
O1G0.017 (4)0.013 (3)0.028 (4)0.004 (3)0.003 (3)0.008 (3)
O2G0.023 (4)0.012 (4)0.039 (4)0.002 (3)0.011 (3)0.008 (3)
N1G0.018 (4)0.011 (4)0.023 (4)0.004 (3)0.006 (3)0.006 (3)
C1G0.012 (4)0.016 (4)0.026 (4)0.001 (3)0.011 (4)0.010 (4)
C21G0.016 (6)0.007 (4)0.015 (4)0.001 (4)0.006 (4)0.000 (4)
C31G0.022 (6)0.020 (5)0.019 (5)0.003 (4)0.004 (4)0.007 (4)
C41G0.036 (9)0.037 (9)0.029 (8)0.000 (7)0.003 (7)0.004 (7)
C22G0.016 (6)0.007 (4)0.015 (4)0.001 (4)0.006 (4)0.000 (4)
C32G0.022 (6)0.020 (5)0.019 (5)0.003 (4)0.004 (4)0.007 (4)
O1B0.011 (3)0.024 (4)0.022 (3)0.007 (3)0.003 (3)0.006 (3)
O2B0.019 (3)0.013 (3)0.034 (4)0.002 (3)0.013 (3)0.009 (3)
N1B0.021 (4)0.016 (4)0.020 (4)0.002 (3)0.005 (3)0.011 (3)
C1B0.016 (4)0.012 (4)0.014 (4)0.005 (3)0.003 (3)0.002 (3)
C21B0.008 (4)0.010 (6)0.017 (4)0.001 (4)0.005 (3)0.000 (3)
C31B0.019 (5)0.017 (5)0.030 (5)0.003 (4)0.009 (4)0.007 (4)
C41B0.035 (6)0.020 (5)0.029 (5)0.003 (4)0.007 (5)0.006 (4)
S11B0.040 (3)0.024 (3)0.0316 (19)0.002 (2)0.0156 (19)0.0039 (17)
C22B0.008 (4)0.010 (6)0.017 (4)0.001 (4)0.005 (3)0.000 (3)
C32B0.019 (5)0.017 (5)0.030 (5)0.003 (4)0.009 (4)0.007 (4)
S12B0.040 (3)0.024 (3)0.0316 (19)0.002 (2)0.0156 (19)0.0039 (17)
C5B0.087 (7)0.069 (7)0.065 (7)0.015 (6)0.027 (6)0.029 (5)
O1C0.021 (3)0.012 (3)0.026 (4)0.005 (3)0.010 (3)0.007 (3)
O2C0.019 (3)0.014 (3)0.031 (4)0.001 (3)0.004 (3)0.008 (3)
N1C0.015 (4)0.016 (4)0.018 (4)0.002 (3)0.004 (3)0.002 (3)
C1C0.011 (4)0.014 (4)0.022 (4)0.001 (3)0.000 (3)0.003 (3)
C21C0.014 (4)0.012 (4)0.020 (4)0.002 (3)0.005 (3)0.002 (3)
C31C0.028 (5)0.021 (4)0.025 (4)0.002 (4)0.007 (3)0.007 (3)
C41C0.074 (9)0.024 (7)0.034 (7)0.006 (6)0.013 (6)0.001 (5)
C22C0.014 (4)0.012 (4)0.020 (4)0.002 (3)0.005 (3)0.002 (3)
C32C0.028 (5)0.021 (4)0.025 (4)0.002 (4)0.007 (3)0.007 (3)
O1A0.025 (4)0.025 (4)0.018 (3)0.003 (3)0.010 (3)0.006 (3)
O2A0.020 (4)0.012 (4)0.046 (4)0.001 (3)0.010 (3)0.011 (3)
N1A0.019 (4)0.007 (4)0.026 (4)0.003 (3)0.005 (4)0.003 (3)
C1A0.012 (4)0.012 (4)0.021 (4)0.001 (3)0.001 (3)0.007 (3)
C2A0.014 (4)0.009 (4)0.022 (4)0.000 (3)0.008 (4)0.001 (3)
C3A0.015 (4)0.017 (4)0.025 (4)0.004 (4)0.004 (4)0.001 (3)
C4A0.043 (6)0.035 (6)0.027 (5)0.001 (5)0.018 (5)0.012 (5)
O1D0.015 (3)0.017 (3)0.023 (4)0.002 (3)0.003 (3)0.003 (3)
O2D0.024 (4)0.010 (3)0.039 (4)0.003 (3)0.010 (3)0.010 (3)
N1D0.021 (4)0.008 (4)0.023 (4)0.002 (3)0.008 (3)0.003 (3)
C1D0.018 (4)0.013 (4)0.019 (4)0.003 (3)0.012 (4)0.000 (3)
C2D0.015 (4)0.012 (4)0.018 (4)0.004 (3)0.002 (3)0.004 (3)
C3D0.028 (5)0.014 (4)0.021 (4)0.001 (4)0.002 (4)0.001 (4)
C4D0.027 (5)0.017 (4)0.007 (4)0.007 (4)0.006 (4)0.001 (3)
S1D0.0380 (16)0.0353 (16)0.0233 (14)0.0049 (13)0.0100 (13)0.0068 (12)
C5D0.052 (7)0.032 (6)0.029 (6)0.017 (5)0.004 (5)0.006 (5)
O1F0.012 (3)0.017 (3)0.026 (4)0.000 (3)0.005 (3)0.005 (3)
O2F0.020 (4)0.009 (3)0.033 (4)0.004 (3)0.013 (3)0.008 (3)
N1F0.010 (4)0.014 (4)0.033 (4)0.003 (3)0.003 (3)0.003 (3)
C1F0.010 (4)0.016 (4)0.018 (4)0.000 (3)0.001 (3)0.011 (3)
C2F0.011 (4)0.010 (4)0.020 (4)0.001 (3)0.010 (3)0.000 (3)
C3F0.024 (5)0.019 (5)0.028 (4)0.001 (4)0.005 (4)0.003 (4)
C4F0.027 (5)0.022 (5)0.033 (5)0.000 (4)0.004 (4)0.001 (4)
S1F0.0382 (16)0.0249 (14)0.0317 (14)0.0074 (12)0.0127 (13)0.0039 (11)
C5F0.041 (6)0.038 (6)0.061 (7)0.006 (5)0.025 (6)0.022 (5)
O1H0.020 (4)0.016 (3)0.028 (4)0.000 (3)0.011 (3)0.009 (3)
O2H0.019 (4)0.012 (4)0.031 (4)0.005 (3)0.007 (3)0.010 (3)
N1H0.017 (4)0.011 (4)0.029 (4)0.002 (3)0.009 (3)0.008 (3)
C1H0.014 (4)0.012 (4)0.020 (4)0.001 (3)0.005 (4)0.006 (3)
C2H0.016 (4)0.009 (4)0.019 (4)0.002 (3)0.001 (3)0.002 (3)
C3H0.023 (5)0.014 (4)0.019 (4)0.001 (4)0.007 (4)0.009 (3)
C4H0.033 (5)0.014 (4)0.014 (4)0.003 (4)0.008 (4)0.003 (3)
S1H0.0378 (16)0.0232 (14)0.0241 (13)0.0045 (11)0.0096 (12)0.0045 (11)
C5H0.048 (7)0.044 (7)0.031 (6)0.005 (5)0.013 (5)0.001 (5)
Geometric parameters (Å, º) top
O1E—C1E1.246 (12)C21C—C31C1.522 (14)
O2E—C1E1.274 (12)C21C—H21C1.0000
N1E—C22E1.45 (8)C31C—C41C1.515 (17)
N1E—C21E1.49 (4)C31C—H31C0.9900
N1E—H1E0.9100C31C—H32C0.9900
N1E—H2E0.9100C41C—H41C0.9800
N1E—H3E0.9100C41C—H42C0.9800
C1E—C22E1.41 (6)C41C—H43C0.9800
C1E—C21E1.56 (3)C32C—C42C1.515 (17)
C21E—C31E1.549 (18)C32C—H33C0.9900
C21E—H21E1.0000C32C—H34C0.9900
C31E—C41E1.516 (18)C42C—H44C0.9800
C31E—H31E0.9900C42C—H45C0.9800
C31E—H32E0.9900C42C—H46C0.9800
C41E—H41E0.9800O1A—C1A1.247 (11)
C41E—H42E0.9800O2A—C1A1.263 (10)
C41E—H43E0.9800N1A—C2A1.510 (11)
C22E—C32E1.548 (18)N1A—H1A0.9100
C22E—H22E1.0000N1A—H2A0.9100
C32E—C42E1.515 (18)N1A—H3A0.9100
C32E—H33E0.9900C1A—C2A1.533 (13)
C32E—H34E0.9900C2A—C3A1.528 (14)
C42E—H44E0.9800C2A—H21A1.0000
C42E—H45E0.9800C3A—C4A1.490 (15)
C42E—H46E0.9800C3A—H31A0.9900
O1G—C1G1.240 (11)C3A—H32A0.9900
O2G—C1G1.257 (11)C4A—H41A0.9800
N1G—C22G1.44 (4)C4A—H42A0.9800
N1G—C21G1.51 (2)C4A—H43A0.9800
N1G—H1G0.9100O1D—C1D1.264 (11)
N1G—H2G0.9100O2D—C1D1.247 (11)
N1G—H3G0.9100N1D—C2D1.494 (11)
C1G—C21G1.55 (3)N1D—H1D0.9100
C1G—C22G1.57 (5)N1D—H2D0.9100
C21G—C31G1.535 (16)N1D—H3D0.9100
C21G—H21G1.0000C1D—C2D1.511 (13)
C31G—C41G1.536 (19)C2D—C3D1.553 (13)
C31G—H31G0.9900C2D—H21D1.0000
C31G—H32G0.9900C3D—C4D1.478 (14)
C41G—H41G0.9800C3D—H3D10.9900
C41G—H42G0.9800C3D—H3D20.9900
C41G—H43G0.9800C4D—S1D1.821 (9)
C22G—C32G1.535 (16)C4D—H41D0.9900
C22G—H22G1.0000C4D—H42D0.9900
C32G—C42G1.535 (19)S1D—C5D1.796 (12)
C32G—H33G0.9900C5D—H51D0.9800
C32G—H34G0.9900C5D—H52D0.9800
C42G—H44G0.9800C5D—H53D0.9800
C42G—H45G0.9800O1F—C1F1.244 (11)
C42G—H46G0.9800O2F—C1F1.263 (11)
O1B—C1B1.241 (11)N1F—C2F1.506 (11)
O2B—C1B1.265 (11)N1F—H1F0.9100
N1B—C22B1.31 (8)N1F—H2F0.9100
N1B—C21B1.524 (16)N1F—H3F0.9100
N1B—H1B0.9100C1F—C2F1.551 (13)
N1B—H2B0.9100C2F—C3F1.532 (14)
N1B—H3B0.9100C2F—H21F1.0000
C1B—C21B1.503 (16)C3F—C4F1.536 (13)
C1B—C22B1.76 (9)C3F—H31F0.9900
C21B—C31B1.560 (16)C3F—H32F0.9900
C21B—H21B1.0000C4F—S1F1.791 (11)
C31B—C41B1.508 (15)C4F—H41F0.9900
C31B—H31B0.9900C4F—H42F0.9900
C31B—H32B0.9900S1F—C5F1.799 (12)
C41B—S11B1.799 (13)C5F—H51F0.9800
C41B—H41B0.9900C5F—H52F0.9800
C41B—H42B0.9900C5F—H53F0.9800
S11B—C5B1.813 (16)O1H—C1H1.257 (11)
C22B—C32B1.560 (16)O2H—C1H1.276 (11)
C22B—H22B1.0000N1H—C2H1.488 (11)
C32B—C42B1.508 (16)N1H—H1H0.9100
C32B—H33B0.9900N1H—H2H0.9100
C32B—H34B0.9900N1H—H3H0.9100
C42B—S12B1.799 (13)C1H—C2H1.520 (13)
C42B—H43B0.9900C2H—C3H1.530 (12)
C42B—H44B0.9900C2H—H21H1.0000
S12B—C5B1.75 (5)C3H—C4H1.520 (12)
C5B—H51B0.9800C3H—H31H0.9900
C5B—H52B0.9800C3H—H32H0.9900
C5B—H53B0.9800C4H—S1H1.804 (9)
O1C—C1C1.259 (11)C4H—H41H0.9900
O2C—C1C1.253 (11)C4H—H42H0.9900
N1C—C21C1.498 (11)S1H—C5H1.788 (12)
N1C—H1C0.9100C5H—H51H0.9800
N1C—H2C0.9100C5H—H52H0.9800
N1C—H3C0.9100C5H—H53H0.9800
C1C—C21C1.517 (14)
C21E—N1E—H1E109.5O1C—C1C—C21C118.0 (8)
C21E—N1E—H2E109.5N1C—C21C—C1C109.2 (7)
H1E—N1E—H2E109.5N1C—C21C—C31C107.9 (8)
C21E—N1E—H3E109.5C1C—C21C—C31C112.5 (9)
H1E—N1E—H3E109.5N1C—C21C—H21C109.1
H2E—N1E—H3E109.5C1C—C21C—H21C109.1
O1E—C1E—O2E125.4 (9)C31C—C21C—H21C109.1
O1E—C1E—C22E115 (3)C41C—C31C—C21C114.5 (10)
O2E—C1E—C22E119 (3)C41C—C31C—H31C108.6
O1E—C1E—C21E118.4 (18)C21C—C31C—H31C108.6
O2E—C1E—C21E116.2 (17)C41C—C31C—H32C108.6
N1E—C21E—C31E107 (3)C21C—C31C—H32C108.6
N1E—C21E—C1E107.8 (19)H31C—C31C—H32C107.6
C31E—C21E—C1E108.5 (18)C31C—C41C—H41C109.5
N1E—C21E—H21E111.2C31C—C41C—H42C109.5
C31E—C21E—H21E111.2H41C—C41C—H42C109.5
C1E—C21E—H21E111.2C31C—C41C—H43C109.5
C41E—C31E—C21E111.6 (19)H41C—C41C—H43C109.5
C41E—C31E—H31E109.3H42C—C41C—H43C109.5
C21E—C31E—H31E109.3C42C—C32C—H33C108.6
C41E—C31E—H32E109.3C42C—C32C—H34C108.6
C21E—C31E—H32E109.3H33C—C32C—H34C107.6
H31E—C31E—H32E108.0C32C—C42C—H44C109.5
C31E—C41E—H41E109.5C32C—C42C—H45C109.5
C31E—C41E—H42E109.5H44C—C42C—H45C109.5
H41E—C41E—H42E109.5C32C—C42C—H46C109.5
C31E—C41E—H43E109.5H44C—C42C—H46C109.5
H41E—C41E—H43E109.5H45C—C42C—H46C109.5
H42E—C41E—H43E109.5C2A—N1A—H1A109.5
C1E—C22E—N1E119 (4)C2A—N1A—H2A109.5
C1E—C22E—C32E117 (3)H1A—N1A—H2A109.5
N1E—C22E—C32E109 (4)C2A—N1A—H3A109.5
C1E—C22E—H22E103.4H1A—N1A—H3A109.5
N1E—C22E—H22E103.4H2A—N1A—H3A109.5
C32E—C22E—H22E103.4O1A—C1A—O2A126.2 (9)
C42E—C32E—C22E111.7 (19)O1A—C1A—C2A117.9 (8)
C42E—C32E—H33E109.3O2A—C1A—C2A115.7 (8)
C22E—C32E—H33E109.3N1A—C2A—C3A110.0 (7)
C42E—C32E—H34E109.3N1A—C2A—C1A107.5 (7)
C22E—C32E—H34E109.3C3A—C2A—C1A111.2 (8)
H33E—C32E—H34E107.9N1A—C2A—H21A109.4
C32E—C42E—H44E109.5C3A—C2A—H21A109.4
C32E—C42E—H45E109.5C1A—C2A—H21A109.4
H44E—C42E—H45E109.5C4A—C3A—C2A115.5 (9)
C32E—C42E—H46E109.5C4A—C3A—H31A108.4
H44E—C42E—H46E109.5C2A—C3A—H31A108.4
H45E—C42E—H46E109.5C4A—C3A—H32A108.4
C21G—N1G—H1G109.5C2A—C3A—H32A108.4
C21G—N1G—H2G109.5H31A—C3A—H32A107.5
H1G—N1G—H2G109.5C3A—C4A—H41A109.5
C21G—N1G—H3G109.5C3A—C4A—H42A109.5
H1G—N1G—H3G109.5H41A—C4A—H42A109.5
H2G—N1G—H3G109.5C3A—C4A—H43A109.5
O1G—C1G—O2G127.7 (9)H41A—C4A—H43A109.5
O1G—C1G—C21G118.9 (12)H42A—C4A—H43A109.5
O2G—C1G—C21G113.4 (12)C2D—N1D—H1D109.5
O1G—C1G—C22G113 (2)C2D—N1D—H2D109.5
O2G—C1G—C22G118.9 (19)H1D—N1D—H2D109.5
N1G—C21G—C31G111.2 (16)C2D—N1D—H3D109.5
N1G—C21G—C1G108.8 (15)H1D—N1D—H3D109.5
C31G—C21G—C1G112.4 (13)H2D—N1D—H3D109.5
N1G—C21G—H21G108.1O2D—C1D—O1D125.6 (9)
C31G—C21G—H21G108.1O2D—C1D—C2D116.7 (8)
C1G—C21G—H21G108.1O1D—C1D—C2D117.6 (8)
C21G—C31G—C41G115.5 (13)N1D—C2D—C1D110.7 (8)
C21G—C31G—H31G108.4N1D—C2D—C3D110.6 (7)
C41G—C31G—H31G108.4C1D—C2D—C3D111.4 (7)
C21G—C31G—H32G108.4N1D—C2D—H21D108.0
C41G—C31G—H32G108.4C1D—C2D—H21D108.0
H31G—C31G—H32G107.5C3D—C2D—H21D108.0
C31G—C41G—H41G109.5C4D—C3D—C2D113.7 (8)
C31G—C41G—H42G109.5C4D—C3D—H3D1108.8
H41G—C41G—H42G109.5C2D—C3D—H3D1108.8
C31G—C41G—H43G109.5C4D—C3D—H3D2108.8
H41G—C41G—H43G109.5C2D—C3D—H3D2108.8
H42G—C41G—H43G109.5H3D1—C3D—H3D2107.7
N1G—C22G—C32G110 (3)C3D—C4D—S1D113.4 (7)
N1G—C22G—C1G111 (3)C3D—C4D—H41D108.9
C32G—C22G—C1G112 (3)S1D—C4D—H41D108.9
N1G—C22G—H22G107.9C3D—C4D—H42D108.9
C32G—C22G—H22G107.9S1D—C4D—H42D108.9
C1G—C22G—H22G107.9H41D—C4D—H42D107.7
C22G—C32G—C42G115.5 (13)C5D—S1D—C4D99.8 (5)
C22G—C32G—H33G108.4S1D—C5D—H51D109.5
C42G—C32G—H33G108.4S1D—C5D—H52D109.5
C22G—C32G—H34G108.4H51D—C5D—H52D109.5
C42G—C32G—H34G108.4S1D—C5D—H53D109.5
H33G—C32G—H34G107.5H51D—C5D—H53D109.5
C32G—C42G—H44G109.5H52D—C5D—H53D109.5
C32G—C42G—H45G109.5C2F—N1F—H1F109.5
H44G—C42G—H45G109.5C2F—N1F—H2F109.5
C32G—C42G—H46G109.5H1F—N1F—H2F109.5
H44G—C42G—H46G109.5C2F—N1F—H3F109.5
H45G—C42G—H46G109.5H1F—N1F—H3F109.5
C21B—N1B—H1B109.5H2F—N1F—H3F109.5
C21B—N1B—H2B109.5O1F—C1F—O2F126.3 (9)
H1B—N1B—H2B109.5O1F—C1F—C2F118.1 (8)
C21B—N1B—H3B109.5O2F—C1F—C2F115.5 (8)
H1B—N1B—H3B109.5N1F—C2F—C3F107.8 (8)
H2B—N1B—H3B109.5N1F—C2F—C1F107.4 (7)
O1B—C1B—O2B126.6 (8)C3F—C2F—C1F112.0 (8)
O1B—C1B—C21B117.7 (10)N1F—C2F—H21F109.9
O2B—C1B—C21B115.5 (10)C3F—C2F—H21F109.9
O1B—C1B—C22B114 (3)C1F—C2F—H21F109.9
O2B—C1B—C22B120 (3)C2F—C3F—C4F112.4 (8)
C1B—C21B—N1B109.6 (10)C2F—C3F—H31F109.1
C1B—C21B—C31B111.5 (9)C4F—C3F—H31F109.1
N1B—C21B—C31B103.1 (12)C2F—C3F—H32F109.1
C1B—C21B—H21B110.8C4F—C3F—H32F109.1
N1B—C21B—H21B110.8H31F—C3F—H32F107.8
C31B—C21B—H21B110.8C3F—C4F—S1F115.9 (7)
C41B—C31B—C21B112.6 (11)C3F—C4F—H41F108.3
C41B—C31B—H31B109.1S1F—C4F—H41F108.3
C21B—C31B—H31B109.1C3F—C4F—H42F108.3
C41B—C31B—H32B109.1S1F—C4F—H42F108.3
C21B—C31B—H32B109.1H41F—C4F—H42F107.4
H31B—C31B—H32B107.8C4F—S1F—C5F100.8 (5)
C31B—C41B—S11B113.6 (9)S1F—C5F—H51F109.5
C31B—C41B—H41B108.8S1F—C5F—H52F109.5
S11B—C41B—H41B108.8H51F—C5F—H52F109.5
C31B—C41B—H42B108.8S1F—C5F—H53F109.5
S11B—C41B—H42B108.8H51F—C5F—H53F109.5
H41B—C41B—H42B107.7H52F—C5F—H53F109.5
C41B—S11B—C5B100.8 (7)C2H—N1H—H1H109.5
N1B—C22B—C32B136 (7)C2H—N1H—H2H109.5
N1B—C22B—C1B106 (4)H1H—N1H—H2H109.5
C32B—C22B—C1B99 (4)C2H—N1H—H3H109.5
N1B—C22B—H22B103.6H1H—N1H—H3H109.5
C32B—C22B—H22B103.6H2H—N1H—H3H109.5
C1B—C22B—H22B103.6O1H—C1H—O2H125.1 (9)
C42B—C32B—C22B112.6 (12)O1H—C1H—C2H118.7 (8)
C42B—C32B—H33B109.1O2H—C1H—C2H116.2 (8)
C22B—C32B—H33B109.1N1H—C2H—C1H109.8 (7)
C42B—C32B—H34B109.1N1H—C2H—C3H109.2 (7)
C22B—C32B—H34B109.1C1H—C2H—C3H113.0 (7)
H33B—C32B—H34B107.8N1H—C2H—H21H108.2
C32B—C42B—S12B113.7 (9)C1H—C2H—H21H108.2
C32B—C42B—H43B108.8C3H—C2H—H21H108.2
S12B—C42B—H43B108.8C4H—C3H—C2H112.8 (7)
C32B—C42B—H44B108.8C4H—C3H—H31H109.0
S12B—C42B—H44B108.8C2H—C3H—H31H109.0
H43B—C42B—H44B107.7C4H—C3H—H32H109.0
C5B—S12B—C42B109 (2)C2H—C3H—H32H109.0
S11B—C5B—H51B109.5H31H—C3H—H32H107.8
S11B—C5B—H52B109.5C3H—C4H—S1H110.6 (7)
H51B—C5B—H52B109.5C3H—C4H—H41H109.5
S11B—C5B—H53B109.5S1H—C4H—H41H109.5
H51B—C5B—H53B109.5C3H—C4H—H42H109.5
H52B—C5B—H53B109.5S1H—C4H—H42H109.5
C21C—N1C—H1C109.5H41H—C4H—H42H108.1
C21C—N1C—H2C109.5C5H—S1H—C4H98.9 (5)
H1C—N1C—H2C109.5S1H—C5H—H51H109.5
C21C—N1C—H3C109.5S1H—C5H—H52H109.5
H1C—N1C—H3C109.5H51H—C5H—H52H109.5
H2C—N1C—H3C109.5S1H—C5H—H53H109.5
O2C—C1C—O1C124.8 (9)H51H—C5H—H53H109.5
O2C—C1C—C21C117.1 (8)H52H—C5H—H53H109.5
O1E—C1E—C21E—N1E21 (2)C32B—C42B—S12B—C5B55 (5)
O2E—C1E—C21E—N1E160.9 (13)O2C—C1C—C21C—N1C154.8 (8)
O1E—C1E—C21E—C31E95 (2)O1C—C1C—C21C—N1C28.7 (11)
O2E—C1E—C21E—C31E84 (3)O2C—C1C—C21C—C31C85.4 (11)
N1E—C21E—C31E—C41E178.9 (15)O1C—C1C—C21C—C31C91.1 (11)
C1E—C21E—C31E—C41E63 (3)N1C—C21C—C31C—C41C175.1 (10)
O1E—C1E—C22E—N1E15 (4)C1C—C21C—C31C—C41C64.4 (13)
O2E—C1E—C22E—N1E163 (3)N1C—C22C—C32C—C42C98 (13)
O1E—C1E—C22E—C32E118 (5)O1A—C1A—C2A—N1A28.7 (11)
O2E—C1E—C22E—C32E64 (5)O2A—C1A—C2A—N1A156.5 (8)
C1E—C22E—C32E—C42E55 (7)O1A—C1A—C2A—C3A91.8 (10)
N1E—C22E—C32E—C42E83 (4)O2A—C1A—C2A—C3A83.0 (10)
O1G—C1G—C21G—N1G10.5 (14)N1A—C2A—C3A—C4A61.1 (11)
O2G—C1G—C21G—N1G167.4 (9)C1A—C2A—C3A—C4A179.9 (8)
O1G—C1G—C21G—C31G113.2 (16)O2D—C1D—C2D—N1D164.2 (8)
O2G—C1G—C21G—C31G69.0 (18)O1D—C1D—C2D—N1D18.1 (11)
N1G—C21G—C31G—C41G74 (2)O2D—C1D—C2D—C3D72.3 (10)
C1G—C21G—C31G—C41G48 (2)O1D—C1D—C2D—C3D105.4 (9)
O1G—C1G—C22G—N1G31 (3)N1D—C2D—C3D—C4D76.5 (10)
O2G—C1G—C22G—N1G156 (2)C1D—C2D—C3D—C4D47.0 (11)
O1G—C1G—C22G—C32G92 (3)C2D—C3D—C4D—S1D176.4 (6)
O2G—C1G—C22G—C32G81 (3)C3D—C4D—S1D—C5D70.4 (8)
N1G—C22G—C32G—C42G177 (3)O1F—C1F—C2F—N1F23.6 (11)
C1G—C22G—C32G—C42G59 (4)O2F—C1F—C2F—N1F160.1 (8)
O1B—C1B—C21B—N1B25.7 (13)O1F—C1F—C2F—C3F94.5 (10)
O2B—C1B—C21B—N1B157.9 (9)O2F—C1F—C2F—C3F81.8 (10)
O1B—C1B—C21B—C31B87.8 (13)N1F—C2F—C3F—C4F169.8 (8)
O2B—C1B—C21B—C31B88.6 (14)C1F—C2F—C3F—C4F72.3 (11)
C1B—C21B—C31B—C41B69.3 (15)C2F—C3F—C4F—S1F69.1 (11)
N1B—C21B—C31B—C41B173.2 (10)C3F—C4F—S1F—C5F72.8 (9)
C21B—C31B—C41B—S11B164.0 (10)O1H—C1H—C2H—N1H20.0 (12)
C31B—C41B—S11B—C5B60.0 (11)O2H—C1H—C2H—N1H160.8 (8)
O1B—C1B—C22B—N1B24 (4)O1H—C1H—C2H—C3H102.2 (10)
O2B—C1B—C22B—N1B158 (3)O2H—C1H—C2H—C3H77.0 (10)
O1B—C1B—C22B—C32B121 (3)N1H—C2H—C3H—C4H168.8 (8)
O2B—C1B—C22B—C32B58 (4)C1H—C2H—C3H—C4H68.7 (10)
N1B—C22B—C32B—C42B70 (10)C2H—C3H—C4H—S1H168.5 (6)
C1B—C22B—C32B—C42B56 (7)C3H—C4H—S1H—C5H178.2 (8)
C22B—C32B—C42B—S12B172 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O1Gi0.911.892.800 (10)174
N1A—H2A···O2Dii0.911.972.832 (10)156
N1A—H3A···O2Biii0.911.962.852 (10)166
C2A—H21A···O1Ci1.002.393.231 (12)142
N1B—H1B···O1H0.911.882.774 (10)168
N1B—H2B···O2A0.911.932.840 (10)175
N1B—H3B···O2C0.911.902.793 (10)168
C21B—H21B···O1D1.002.433.242 (16)138
N1C—H1C···O1E0.911.852.746 (10)167
N1C—H2C···O2Biii0.911.932.818 (10)166
N1C—H3C···O2Diii0.911.922.818 (10)171
C21C—H21C···O1A1.002.353.235 (12)147
N1D—H1D···O2C0.911.952.834 (10)163
N1D—H2D···O2Aiv0.911.932.779 (10)154
N1D—H3D···O1Fiv0.911.892.769 (11)162
C2D—H21D···O1Biv1.002.213.183 (12)165
N1E—H1E···O2H0.911.942.842 (10)171
N1E—H2E···O1A0.911.902.795 (10)166
N1E—H3E···O2F0.911.922.802 (10)164
C21E—H21E···O1Gi1.002.373.21 (3)141
N1F—H1F···O2Ev0.911.942.788 (10)155
N1F—H2F···O1B0.911.872.777 (10)175
N1F—H3F···O2Gvi0.911.952.833 (10)163
C2F—H21F···O1H1.002.363.160 (11)136
N1G—H1G···O2Fiv0.911.972.842 (10)161
N1G—H2G···O1C0.911.962.817 (10)157
N1G—H3G···O2H0.911.952.809 (10)157
C21G—H21G···O1E1.002.083.08 (2)173
N1H—H1H···O2Gv0.911.912.797 (10)163
N1H—H2H···O1D0.911.892.739 (10)155
N1H—H3H···O2Ev0.911.912.810 (10)170
C2H—H21H···O1Fiv1.002.203.181 (11)168
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z; (iii) x, y+1, z; (iv) x1, y, z; (v) x, y1, z; (vi) x+1, y1, z.
(293) (S)-2-aminobutanoic acid–(R)-2-amino-4-(methylsulfanyl)butanoic acid (1/1) top
Crystal data top
C4H9NO2·C5H11NO2SF(000) = 544
Mr = 252.33Dx = 1.253 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
a = 29.1721 (18) ÅCell parameters from 3860 reflections
b = 4.7784 (3) Åθ = 2.3–26.6°
c = 9.8551 (6) ŵ = 0.24 mm1
β = 103.145 (2)°T = 293 K
V = 1337.77 (14) Å3Plate, colorless
Z = 40.78 × 0.76 × 0.10 mm
Data collection top
Bruker D8 Venture with Photon 100 CMOS detector
diffractometer
2924 independent reflections
Radiation source: fine-focus sealed tube1938 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 8.3 pixels mm-1θmax = 27.1°, θmin = 2.3°
Sets of exposures each taken over 0.5° ω rotation scansh = 3636
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2012)
k = 66
Tmin = 0.907, Tmax = 1.000l = 1211
9324 measured reflections
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0605P)2 + 0.2255P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.043(Δ/σ)max < 0.001
wR(F2) = 0.123Δρmax = 0.14 e Å3
S = 1.04Δρmin = 0.15 e Å3
2924 reflectionsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
257 parametersExtinction coefficient: 0.035 (5)
271 restraintsAbsolute structure: Flack x determined using 724 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
Hydrogen site location: inferred from neighbouring sitesAbsolute structure parameter: 0.02 (5)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The side chains of L-Abu and D-Met are disordered over three and four positions, repspectively. Restrainst were applied for molecular geometry with EADP constraints for thermal displacement parameters of equivalent atoms separated by < 1.2 angstrom.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1A0.28775 (9)0.5234 (9)0.4654 (2)0.0517 (9)
O2A0.32151 (9)0.7874 (9)0.3310 (2)0.0635 (11)
N1A0.30377 (9)0.8918 (9)0.6726 (2)0.0453 (11)
H1A0.31291.01760.73990.068*
H2A0.30580.72110.70970.068*
H3A0.27410.92580.62850.068*
C1A0.31155 (14)0.7292 (11)0.4435 (4)0.0420 (13)
C21A0.3354 (4)0.910 (10)0.570 (4)0.0364 (16)0.503 (11)
H21A0.33791.10470.54070.044*0.503 (11)
C31A0.3836 (6)0.798 (5)0.639 (3)0.063 (3)0.503 (11)
H31A0.37960.60850.66960.076*0.503 (11)
H32A0.40180.78510.56790.076*0.503 (11)
C41A0.4105 (4)0.946 (3)0.7521 (12)0.131 (7)0.503 (11)
H41A0.44020.85380.78460.196*0.503 (11)
H42A0.39400.95250.82590.196*0.503 (11)
H43A0.41581.13310.72350.196*0.503 (11)
C22A0.3321 (6)0.91 (2)0.562 (8)0.0364 (16)0.253 (10)
H22A0.33081.10450.52900.044*0.253 (10)
C32A0.3831 (10)0.836 (13)0.622 (5)0.063 (3)0.253 (10)
H33A0.39270.92860.71210.076*0.253 (10)
H34A0.38470.63640.63980.076*0.253 (10)
C42A0.4163 (5)0.902 (6)0.544 (2)0.104 (10)0.253 (10)
H44A0.44720.85010.59570.156*0.253 (10)
H45A0.41561.09970.52600.156*0.253 (10)
H46A0.40900.80190.45760.156*0.253 (10)
C23A0.3243 (7)0.934 (9)0.567 (4)0.0364 (16)0.244 (11)
H23A0.31411.11910.52910.044*0.244 (11)
C33A0.3776 (8)0.944 (6)0.609 (3)0.063 (3)0.244 (11)
H35A0.38891.01310.52980.076*0.244 (11)
H36A0.38631.08180.68270.076*0.244 (11)
C43A0.4018 (8)0.696 (6)0.655 (4)0.125 (17)0.244 (11)
H47A0.43480.73520.68730.188*0.244 (11)
H48A0.39750.56490.57870.188*0.244 (11)
H49A0.38980.61640.72900.188*0.244 (11)
O1B0.28793 (9)0.6506 (8)0.0356 (3)0.0512 (9)
O2B0.32233 (9)0.3862 (9)0.1687 (2)0.0607 (10)
N1B0.30318 (9)0.2820 (9)0.1724 (2)0.0434 (10)
H1B0.31490.15250.23570.065*
H2B0.27250.25180.14020.065*
H3B0.30750.45080.21140.065*
C1B0.31143 (13)0.4472 (10)0.0566 (4)0.0389 (11)
C21B0.3277 (4)0.267 (9)0.055 (2)0.0406 (18)0.346 (10)
H21B0.31850.08190.01440.049*0.346 (10)
C31B0.3815 (4)0.232 (3)0.1195 (19)0.068 (5)0.346 (10)
H31B0.38610.10950.19970.082*0.346 (10)
H32B0.39670.14880.05150.082*0.346 (10)
C41B0.4034 (4)0.518 (3)0.1636 (18)0.085 (6)0.346 (10)
H41B0.38790.60220.23090.103*0.346 (10)
H42B0.39890.64050.08310.103*0.346 (10)
S11B0.4656 (4)0.483 (4)0.2397 (18)0.219 (10)0.346 (10)
C51B0.4837 (7)0.428 (12)0.083 (3)0.350*0.346 (10)
H51B0.51740.41910.10220.525*0.346 (10)
H52B0.47280.57910.02010.525*0.346 (10)
H53B0.47070.25470.04170.525*0.346 (10)
C22B0.3345 (4)0.261 (8)0.074 (3)0.0406 (18)0.319 (7)
H22B0.33690.06590.04520.049*0.319 (7)
C32B0.3845 (4)0.392 (3)0.1251 (15)0.042 (5)0.319 (7)
H33B0.40150.38400.05120.050*0.319 (7)
H34B0.38170.58670.14970.050*0.319 (7)
C42B0.4116 (4)0.230 (3)0.2521 (11)0.082 (6)0.319 (7)
H43B0.41430.03560.22710.098*0.319 (7)
H44B0.39450.23780.32560.098*0.319 (7)
S12B0.4696 (4)0.376 (3)0.3146 (15)0.204 (6)0.319 (7)
C52B0.4883 (9)0.142 (6)0.454 (2)0.350*0.319 (7)
H54B0.51930.19320.50500.525*0.319 (7)
H55B0.48900.04460.41870.525*0.319 (7)
H56B0.46690.14980.51510.525*0.319 (7)
C23B0.3327 (5)0.231 (6)0.069 (5)0.0406 (18)0.263 (9)
H23B0.33550.03580.04170.049*0.263 (9)
C33B0.3791 (5)0.371 (3)0.153 (2)0.053 (8)0.263 (9)
H35B0.37320.56550.17040.063*0.263 (9)
H36B0.38950.27700.24180.063*0.263 (9)
C43B0.4174 (5)0.350 (6)0.0700 (15)0.101 (8)0.263 (9)
H45B0.40700.44390.01900.122*0.263 (9)
H46B0.42320.15540.05230.122*0.263 (9)
S13B0.4710 (5)0.511 (5)0.1665 (19)0.171 (7)0.263 (9)
C53B0.4901 (10)0.228 (9)0.280 (4)0.350*0.263 (9)
H57B0.52110.26570.33450.525*0.263 (9)
H58B0.49080.06070.22580.525*0.263 (9)
H59B0.46880.20210.33990.525*0.263 (9)
C24B0.3300 (7)0.292 (12)0.078 (4)0.0406 (18)0.070 (5)
H24B0.32590.09910.04370.049*0.070 (5)
C34B0.3827 (8)0.277 (5)0.159 (4)0.053 (8)0.070 (5)
H37B0.38970.43220.22420.063*0.070 (5)
H38B0.38820.10430.21220.063*0.070 (5)
C44B0.4147 (5)0.290 (12)0.057 (3)0.101 (8)0.070 (5)
H47B0.40910.46260.00360.122*0.070 (5)
H48B0.40760.13480.00840.122*0.070 (5)
S14B0.4758 (6)0.273 (10)0.148 (2)0.171 (7)0.070 (5)
C54B0.50000.294 (18)0.00000.19 (3)*0.140 (10)
H60B0.53370.30360.02890.282*0.070 (5)
H61B0.48830.45790.05270.282*0.070 (5)
H62B0.49120.13050.05680.282*0.070 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0712 (17)0.044 (3)0.0406 (15)0.0119 (18)0.0131 (13)0.0098 (15)
O2A0.115 (2)0.046 (3)0.0353 (14)0.000 (2)0.0288 (14)0.001 (2)
N1A0.0648 (17)0.040 (3)0.0307 (15)0.001 (2)0.0089 (15)0.0014 (18)
C1A0.060 (2)0.035 (4)0.032 (2)0.005 (2)0.013 (2)0.006 (2)
C21A0.048 (4)0.034 (3)0.029 (3)0.002 (4)0.013 (3)0.001 (3)
C31A0.060 (4)0.078 (12)0.046 (7)0.014 (6)0.001 (4)0.016 (7)
C41A0.084 (7)0.130 (16)0.145 (11)0.027 (9)0.043 (7)0.068 (10)
C22A0.048 (4)0.034 (3)0.029 (3)0.002 (4)0.013 (3)0.001 (3)
C32A0.060 (4)0.078 (12)0.046 (7)0.014 (6)0.001 (4)0.016 (7)
C42A0.043 (8)0.16 (2)0.120 (16)0.014 (12)0.036 (10)0.005 (16)
C23A0.048 (4)0.034 (3)0.029 (3)0.002 (4)0.013 (3)0.001 (3)
C33A0.060 (4)0.078 (12)0.046 (7)0.014 (6)0.001 (4)0.016 (7)
C43A0.050 (15)0.14 (3)0.15 (3)0.025 (16)0.040 (16)0.07 (2)
O1B0.0721 (17)0.036 (2)0.0457 (16)0.0035 (18)0.0130 (14)0.0007 (15)
O2B0.109 (2)0.043 (3)0.0350 (14)0.000 (2)0.0287 (14)0.0014 (18)
N1B0.0660 (17)0.037 (3)0.0296 (14)0.0062 (19)0.0160 (14)0.0052 (18)
C1B0.060 (2)0.027 (3)0.029 (2)0.012 (2)0.009 (2)0.001 (2)
C21B0.055 (3)0.033 (4)0.034 (3)0.007 (3)0.009 (2)0.000 (3)
C31B0.090 (11)0.062 (9)0.058 (9)0.023 (8)0.030 (8)0.007 (8)
C41B0.090 (12)0.085 (12)0.085 (11)0.021 (9)0.025 (9)0.015 (9)
S11B0.087 (6)0.26 (2)0.27 (2)0.046 (8)0.037 (10)0.051 (18)
C22B0.055 (3)0.033 (4)0.034 (3)0.007 (3)0.009 (2)0.000 (3)
C32B0.044 (10)0.044 (11)0.044 (10)0.004 (9)0.023 (8)0.003 (9)
C42B0.066 (8)0.105 (18)0.066 (8)0.003 (10)0.006 (7)0.001 (10)
S12B0.119 (6)0.263 (13)0.187 (9)0.040 (7)0.057 (5)0.059 (8)
C23B0.055 (3)0.033 (4)0.034 (3)0.007 (3)0.009 (2)0.000 (3)
C33B0.045 (9)0.057 (18)0.058 (12)0.010 (10)0.016 (8)0.014 (12)
C43B0.077 (10)0.136 (18)0.086 (10)0.012 (12)0.006 (8)0.004 (13)
S13B0.085 (5)0.203 (14)0.210 (11)0.047 (7)0.002 (6)0.013 (11)
C24B0.055 (3)0.033 (4)0.034 (3)0.007 (3)0.009 (2)0.000 (3)
C34B0.045 (9)0.057 (18)0.058 (12)0.010 (10)0.016 (8)0.014 (12)
C44B0.077 (10)0.136 (18)0.086 (10)0.012 (12)0.006 (8)0.004 (13)
S14B0.085 (5)0.203 (14)0.210 (11)0.047 (7)0.002 (6)0.013 (11)
Geometric parameters (Å, º) top
O1A—C1A1.251 (5)C21B—C31B1.563 (12)
O2A—C1A1.240 (4)C21B—H21B0.9800
N1A—C23A1.33 (4)C31B—C41B1.528 (13)
N1A—C22A1.51 (6)C31B—H31B0.9700
N1A—C21A1.52 (3)C31B—H32B0.9700
N1A—H1A0.8900C41B—S11B1.805 (9)
N1A—H2A0.8900C41B—H41B0.9700
N1A—H3A0.8900C41B—H42B0.9700
C1A—C22A1.47 (9)S11B—C51B1.761 (18)
C1A—C23A1.54 (4)C51B—H51B0.9600
C1A—C21A1.55 (4)C51B—H52B0.9600
C21A—C31A1.513 (9)C51B—H53B0.9600
C21A—H21A0.9800C22B—C32B1.564 (12)
C31A—C41A1.40 (2)C22B—H22B0.9800
C31A—H31A0.9700C32B—C42B1.529 (13)
C31A—H32A0.9700C32B—H33B0.9700
C41A—H41A0.9600C32B—H34B0.9700
C41A—H42A0.9600C42B—S12B1.804 (9)
C41A—H43A0.9600C42B—H43B0.9700
C22A—C32A1.514 (9)C42B—H44B0.9700
C22A—H22A0.9800S12B—C52B1.761 (18)
C32A—C42A1.40 (2)C52B—H54B0.9600
C32A—H33A0.9700C52B—H55B0.9600
C32A—H34A0.9700C52B—H56B0.9600
C42A—H44A0.9600C23B—C33B1.563 (12)
C42A—H45A0.9600C23B—H23B0.9800
C42A—H46A0.9600C33B—C43B1.529 (13)
C23A—C33A1.514 (9)C33B—H35B0.9700
C23A—H23A0.9800C33B—H36B0.9700
C33A—C43A1.40 (2)C43B—S13B1.806 (9)
C33A—H35A0.9700C43B—H45B0.9700
C33A—H36A0.9700C43B—H46B0.9700
C43A—H47A0.9600S13B—C53B1.761 (18)
C43A—H48A0.9600C53B—H57B0.9600
C43A—H49A0.9600C53B—H58B0.9600
O1B—C1B1.233 (5)C53B—H59B0.9600
O2B—C1B1.252 (4)C24B—C34B1.563 (12)
N1B—C24B1.34 (3)C24B—H24B0.9800
N1B—C22B1.48 (3)C34B—C44B1.528 (13)
N1B—C21B1.50 (2)C34B—H37B0.9700
N1B—C23B1.50 (5)C34B—H38B0.9700
N1B—H1B0.8900C44B—S14B1.805 (9)
N1B—H2B0.8900C44B—H47B0.9700
N1B—H3B0.8900C44B—H48B0.9700
C1B—C21B1.39 (3)S14B—C54B1.762 (18)
C1B—C24B1.51 (3)C54B—H60B0.9600
C1B—C22B1.58 (4)C54B—H61B0.9600
C1B—C23B1.62 (3)C54B—H62B0.9600
C21A—N1A—H1A109.5C41B—C31B—H32B109.7
C21A—N1A—H2A109.5C21B—C31B—H32B109.7
H1A—N1A—H2A109.5H31B—C31B—H32B108.2
C21A—N1A—H3A109.5C31B—C41B—S11B110.5 (8)
H1A—N1A—H3A109.5C31B—C41B—H41B109.6
H2A—N1A—H3A109.5S11B—C41B—H41B109.6
O2A—C1A—O1A125.7 (4)C31B—C41B—H42B109.6
O2A—C1A—C22A116 (3)S11B—C41B—H42B109.6
O1A—C1A—C22A118 (3)H41B—C41B—H42B108.1
O2A—C1A—C23A119.9 (17)C51B—S11B—C41B97.1 (8)
O1A—C1A—C23A114.1 (16)S11B—C51B—H51B109.5
O2A—C1A—C21A116.1 (14)S11B—C51B—H52B109.5
O1A—C1A—C21A117.8 (14)H51B—C51B—H52B109.5
C31A—C21A—N1A109 (2)S11B—C51B—H53B109.5
C31A—C21A—C1A111 (3)H51B—C51B—H53B109.5
N1A—C21A—C1A105.9 (17)H52B—C51B—H53B109.5
C31A—C21A—H21A110.2N1B—C22B—C32B115.4 (13)
N1A—C21A—H21A110.2N1B—C22B—C1B106.5 (13)
C1A—C21A—H21A110.2C32B—C22B—C1B103 (2)
C41A—C31A—C21A118 (2)N1B—C22B—H22B110.4
C41A—C31A—H31A107.8C32B—C22B—H22B110.4
C21A—C31A—H31A107.8C1B—C22B—H22B110.4
C41A—C31A—H32A107.8C42B—C32B—C22B109.5 (16)
C21A—C31A—H32A107.8C42B—C32B—H33B109.8
H31A—C31A—H32A107.1C22B—C32B—H33B109.8
C31A—C41A—H41A109.5C42B—C32B—H34B109.8
C31A—C41A—H42A109.5C22B—C32B—H34B109.8
H41A—C41A—H42A109.5H33B—C32B—H34B108.2
C31A—C41A—H43A109.5C32B—C42B—S12B110.8 (8)
H41A—C41A—H43A109.5C32B—C42B—H43B109.5
H42A—C41A—H43A109.5S12B—C42B—H43B109.5
C1A—C22A—N1A110 (4)C32B—C42B—H44B109.5
C1A—C22A—C32A111 (5)S12B—C42B—H44B109.5
N1A—C22A—C32A111 (5)H43B—C42B—H44B108.1
C1A—C22A—H22A108.2C52B—S12B—C42B97.0 (8)
N1A—C22A—H22A108.2S12B—C52B—H54B109.5
C32A—C22A—H22A108.2S12B—C52B—H55B109.5
C42A—C32A—C22A118 (2)H54B—C52B—H55B109.5
C42A—C32A—H33A107.8S12B—C52B—H56B109.5
C22A—C32A—H33A107.8H54B—C52B—H56B109.5
C42A—C32A—H34A107.8H55B—C52B—H56B109.5
C22A—C32A—H34A107.8N1B—C23B—C33B98 (2)
H33A—C32A—H34A107.1N1B—C23B—C1B103.6 (17)
C32A—C42A—H44A109.5C33B—C23B—C1B105.5 (16)
C32A—C42A—H45A109.5N1B—C23B—H23B115.9
H44A—C42A—H45A109.5C33B—C23B—H23B115.9
C32A—C42A—H46A109.5C1B—C23B—H23B115.9
H44A—C42A—H46A109.5C43B—C33B—C23B109.9 (16)
H45A—C42A—H46A109.5C43B—C33B—H35B109.7
N1A—C23A—C33A114 (3)C23B—C33B—H35B109.7
N1A—C23A—C1A117 (3)C43B—C33B—H36B109.7
C33A—C23A—C1A107 (2)C23B—C33B—H36B109.7
N1A—C23A—H23A106.2H35B—C33B—H36B108.2
C33A—C23A—H23A106.2C33B—C43B—S13B110.1 (8)
C1A—C23A—H23A106.2C33B—C43B—H45B109.6
C43A—C33A—C23A118 (2)S13B—C43B—H45B109.6
C43A—C33A—H35A107.8C33B—C43B—H46B109.6
C23A—C33A—H35A107.8S13B—C43B—H46B109.6
C43A—C33A—H36A107.8H45B—C43B—H46B108.2
C23A—C33A—H36A107.8C53B—S13B—C43B96.8 (8)
H35A—C33A—H36A107.1S13B—C53B—H57B109.5
C33A—C43A—H47A109.5S13B—C53B—H58B109.5
C33A—C43A—H48A109.5H57B—C53B—H58B109.5
H47A—C43A—H48A109.5S13B—C53B—H59B109.5
C33A—C43A—H49A109.5H57B—C53B—H59B109.5
H47A—C43A—H49A109.5H58B—C53B—H59B109.5
H48A—C43A—H49A109.5N1B—C24B—C1B118.4 (18)
C21B—N1B—H1B109.5N1B—C24B—C34B108 (2)
C21B—N1B—H2B109.5C1B—C24B—C34B126 (2)
H1B—N1B—H2B109.5N1B—C24B—H24B99.4
C21B—N1B—H3B109.5C1B—C24B—H24B99.4
H1B—N1B—H3B109.5C34B—C24B—H24B99.4
H2B—N1B—H3B109.5C44B—C34B—C24B109.8 (16)
O1B—C1B—O2B126.4 (4)C44B—C34B—H37B109.7
O1B—C1B—C21B117.3 (14)C24B—C34B—H37B109.7
O2B—C1B—C21B116.3 (15)C44B—C34B—H38B109.7
O1B—C1B—C24B110 (2)C24B—C34B—H38B109.7
O2B—C1B—C24B123.4 (19)H37B—C34B—H38B108.2
O1B—C1B—C22B117.2 (8)C34B—C44B—S14B110.5 (8)
O2B—C1B—C22B116.0 (8)C34B—C44B—H47B109.5
O1B—C1B—C23B120.3 (17)S14B—C44B—H47B109.5
O2B—C1B—C23B113.3 (17)C34B—C44B—H48B109.5
C1B—C21B—N1B116 (2)S14B—C44B—H48B109.5
C1B—C21B—C31B121.1 (13)H47B—C44B—H48B108.1
N1B—C21B—C31B107.6 (10)C54B—S14B—C44B96.9 (8)
C1B—C21B—H21B103.1S14B—C54B—H60B109.5
N1B—C21B—H21B103.1S14B—C54B—H61B109.5
C31B—C21B—H21B103.1H60B—C54B—H61B109.5
C41B—C31B—C21B109.9 (16)S14B—C54B—H62B109.5
C41B—C31B—H31B109.7H60B—C54B—H62B109.5
C21B—C31B—H31B109.7H61B—C54B—H62B109.5
C23A—N1A—C21A—C31A175 (16)O1B—C1B—C22B—N1B29.4 (18)
C23A—N1A—C21A—C1A66 (13)O2B—C1B—C22B—N1B156.4 (9)
O2A—C1A—C21A—C31A86 (2)C21B—C1B—C22B—N1B62 (16)
O1A—C1A—C21A—C31A87.8 (19)C24B—C1B—C22B—N1B23 (16)
C23A—C1A—C21A—C31A163 (13)C23B—C1B—C22B—N1B97 (22)
O2A—C1A—C21A—N1A156.1 (15)O1B—C1B—C22B—C32B92.5 (11)
O1A—C1A—C21A—N1A30 (3)O2B—C1B—C22B—C32B81.7 (12)
C23A—C1A—C21A—N1A45 (10)C21B—C1B—C22B—C32B176 (17)
N1A—C21A—C31A—C41A66 (3)C24B—C1B—C22B—C32B99 (16)
C1A—C21A—C31A—C41A177.7 (19)C23B—C1B—C22B—C32B141 (22)
O2A—C1A—C22A—N1A158 (3)N1B—C22B—C32B—C42B65 (3)
O1A—C1A—C22A—N1A25 (5)C1B—C22B—C32B—C42B179.6 (7)
C23A—C1A—C22A—N1A44 (21)C22B—C32B—C42B—S12B179.9 (4)
O2A—C1A—C22A—C32A79 (5)C32B—C42B—S12B—C52B180.0 (4)
O1A—C1A—C22A—C32A98 (3)C24B—N1B—C23B—C33B63 (9)
C1A—C22A—C32A—C42A71 (5)C22B—N1B—C23B—C33B40 (19)
N1A—C22A—C32A—C42A166 (6)C21B—N1B—C23B—C33B110 (11)
C21A—N1A—C23A—C33A26 (12)C24B—N1B—C23B—C1B45 (9)
C21A—N1A—C23A—C1A99 (15)C22B—N1B—C23B—C1B68 (19)
O2A—C1A—C23A—N1A165.3 (14)C21B—N1B—C23B—C1B2 (10)
O1A—C1A—C23A—N1A9 (2)O1B—C1B—C23B—N1B19.9 (15)
C21A—C1A—C23A—N1A119 (12)O2B—C1B—C23B—N1B161.5 (10)
O2A—C1A—C23A—C33A66 (3)C24B—C1B—C23B—N1B40 (5)
O1A—C1A—C23A—C33A120 (2)C22B—C1B—C23B—N1B76 (22)
C22A—C1A—C23A—C33A5 (23)O1B—C1B—C23B—C33B82 (2)
C21A—C1A—C23A—C33A10 (10)O2B—C1B—C23B—C33B96 (2)
N1A—C23A—C33A—C43A69 (5)C24B—C1B—C23B—C33B62 (6)
C1A—C23A—C33A—C43A61 (5)C22B—C1B—C23B—C33B26 (20)
O1B—C1B—C21B—N1B19 (2)N1B—C23B—C33B—C43B180.0 (7)
O2B—C1B—C21B—N1B161.3 (13)C1B—C23B—C33B—C43B73 (2)
C24B—C1B—C21B—N1B55 (8)C23B—C33B—C43B—S13B180.0 (4)
C22B—C1B—C21B—N1B110 (18)C33B—C43B—S13B—C53B80 (2)
O1B—C1B—C21B—C31B115 (2)C22B—N1B—C24B—C1B144 (22)
O2B—C1B—C21B—C31B65 (3)C21B—N1B—C24B—C1B68 (13)
C24B—C1B—C21B—C31B79 (5)C23B—N1B—C24B—C1B123 (12)
C22B—C1B—C21B—C31B24 (14)C22B—N1B—C24B—C34B65 (16)
C24B—N1B—C21B—C1B99 (17)C21B—N1B—C24B—C34B142 (18)
C22B—N1B—C21B—C1B141 (19)C23B—N1B—C24B—C34B86 (8)
C23B—N1B—C21B—C1B178 (12)O1B—C1B—C24B—N1B34 (5)
C24B—N1B—C21B—C31B40 (14)O2B—C1B—C24B—N1B151 (3)
C22B—N1B—C21B—C31B2 (16)C21B—C1B—C24B—N1B112 (8)
C23B—N1B—C21B—C31B38 (9)C22B—C1B—C24B—N1B152 (20)
C1B—C21B—C31B—C41B55 (3)C23B—C1B—C24B—N1B127 (9)
N1B—C21B—C31B—C41B82 (2)O1B—C1B—C24B—C34B111 (4)
C21B—C31B—C41B—S11B179.6 (4)O2B—C1B—C24B—C34B64 (6)
C31B—C41B—S11B—C51B75 (2)C21B—C1B—C24B—C34B103 (8)
C24B—N1B—C22B—C32B83 (19)C22B—C1B—C24B—C34B63 (14)
C21B—N1B—C22B—C32B145 (20)C23B—C1B—C24B—C34B88 (4)
C23B—N1B—C22B—C32B141 (22)N1B—C24B—C34B—C44B179.5 (9)
C24B—N1B—C22B—C1B31 (18)C1B—C24B—C34B—C44B32 (8)
C21B—N1B—C22B—C1B31 (17)C24B—C34B—C44B—S14B180.0 (4)
C23B—N1B—C22B—C1B105 (19)C34B—C44B—S14B—C54B179.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O2Bi0.891.972.817 (5)159
N1A—H2A···O2Bii0.891.992.862 (5)165
N1A—H3A···O1Aiii0.891.892.779 (4)176
C21A—H21A···O1Aiv0.982.493.31 (4)141
N1B—H1B···O2Av0.891.972.817 (5)158
N1B—H2B···O1Bvi0.891.892.765 (4)167
N1B—H3B···O2A0.891.982.860 (5)169
C21B—H21B···O1Bv0.982.263.21 (4)166
Symmetry codes: (i) x, y+1, z+1; (ii) x, y, z+1; (iii) x+1/2, y+1/2, z+1; (iv) x, y+1, z; (v) x, y1, z; (vi) x+1/2, y1/2, z.
Molecular conformations at 293 and 103 K top
TorsionN1—C2—C3—C4C2—C3—C4—S1C3—C4—S1—C5
293 K*
Residue, conformation number, occupancy
L-Abu, 1, 0.503 (11)-66 (3)--
gauche---
L-Abu, 2, 0.253 (10)-166 (3)--
trans--
L-Abu, 3, 0.244 (11)69 (5)--
gauche+--
D-Met, 1, 0.346 (10)-82 (2)179.6 (4)75 (2)
gauche-transgauche+
D-Met, 2, 0.319 (7)65 (3)-179.9 (4)-180.0 (4)
gauche+transtrans
D-Met, 3, 0.263 (9)180.0 (7)180.0 (4)80 (2)
transtransgauche+
D-Met, 4, 0.070 (5)-179.5 (4)180.0 (4)-179.9 (4)
transtranstrans
103 K
Residue, conformation number, occupancy
L-Abu, A, 1.000-61.1 (11)--
gauche---
L-Abu, C, 0.932 (18)-175.1 (10)--
trans--
L-Abu, C, 0.068 (18)98 (13)--
gauche+--
L-Abu E, 0.649 (19)178.9 (15)--
trans--
L-Abu, E, 0.351 (19)83 (4)--
gauche+--
L-Abu, G, 0.654 (16)74 (2)--
gauche+--
L-Abu, G, 0.346 (16)-177 (3)--
trans--
D-Met, B, 0.832 (16)173.2 (10)164.0 (10)60.0 (11)
transtransgauche+
D-Met, B, 0.168 (16)-70 (10)172 (6)-55 (5)
gauche-transgauche-
D-Met, D, 1.000-76.5 (5)-176.4 (6)70.4 (8)
gauche-transgauche+
D-Met, F, 1.000169.8 (8)-69.1 (11)-72.8 (9)
transgauche-gauche-
D-Met, H, 1.000168.8 (8)-168.5 (6)-178.2 (8)
transtranstrans
Note: (*) the indicated s.u. values at 293 K are unreliable due to use of restraints in the refinement.
 

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