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The amino acid L-isoleucine has been cocrystallized with seven selected D-amino acids including D-methionine [L-­isoleucine–D-methionine (1/1), C6H13NO2.­C5H11­NO2S, amino-acid side chain R = —CH2—CH2—S—CH3] and a homologous series from D-alanine ­[L-­isoleucine–D-alanine (1/1), C6H13NO2.C3H7NO2, R = —CH3] through D-α-aminobutyric acid [L-iso­leucine–D-α-aminobutyric acid (1/1), C6H13NO2.C4H9­NO2, R = —CH2—CH3] and D-norvaline [L-isoleucine–D-norvaline (1/1), C6H13NO2.C5H11NO2, R = —CH2—CH2—CH3] to D-norleucine [L-isoleucine–D-norleucine (1/1), C6H13NO2.C6H13NO2, R = —CH2—CH2—CH2—CH3] with linear side chains, and D-valine [L-isoleucine–D-valine (1/1), C6H13NO2.C5H11NO2, R = —CH—(CH3)2] and D-leucine [L-isoleucine–D-leucine (1/1), C6H13NO2.C6H13NO2, R = —CH2—CH—(CH3)2] with branched side chains. All the crystal structures are divided into distinct hydrophilic and hydrophobic layers. In the five complexes with amino acids with linear side chains the polar parts of the D- and L-amino acids are related by pseudo-glide-plane symmetry, and four of them have remarkably similar molecular arrangements. The D-valine and D-leucine complexes, on the other hand, are structurally quite different with the polar parts of the D- and L-amino acids related by pseudo-inversion. Differences in the hydrogen-bond pattern in the two molecular arrangements are discussed.

Supporting information

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Supplementary material

cif

Crystallographic Information File (CIF)
Contains datablocks L1, L2, L3, L4, L5, B1, B2, global

fcf

Structure factor file (CIF format)
Contains datablock l-ile:d-val

fcf

Structure factor file (CIF format)
Contains datablock l-ile:d-leu

fcf

Structure factor file (CIF format)
Contains datablock l-ile:d-ala

fcf

Structure factor file (CIF format)
Contains datablock l-ile:d-n-abut

fcf

Structure factor file (CIF format)
Contains datablock l-ile:d-nval

fcf

Structure factor file (CIF format)
Contains datablock l-ile:d-nleu

fcf

Structure factor file (CIF format)
Contains datablock l-ile:d-met

hkl

Structure factor file (CIF format)
Contains datablock B1

hkl

Structure factor file (CIF format)
Contains datablock B2

hkl

Structure factor file (CIF format)
Contains datablock L1

hkl

Structure factor file (CIF format)
Supplementary material

hkl

Structure factor file (CIF format)
Supplementary material

hkl

Structure factor file (CIF format)
Supplementary material

hkl

Structure factor file (CIF format)
Supplementary material

CCDC references: 131793; 131794; 131795; 131796; 131797; 131798; 131799

Computing details top

For all compounds, data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 1994).

(L1) L-Isoleucine:D-Alanine top
Crystal data top
C6H13NO2·C3H7NO2F(000) = 240
Mr = 220.27Dx = 1.210 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.8944 (2) ÅCell parameters from 6890 reflections
b = 4.7425 (1) ŵ = 0.09 mm1
c = 12.9045 (2) ÅT = 150 K
β = 93.374 (1)°Plate, colourless
V = 604.48 (2) Å31.05 × 0.25 × 0.05 mm
Z = 2
Data collection top
Siemens SMART CCD area-detector
diffractometer
8985 independent reflections
Radiation source: fine-focus sealed tube6393 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
ω scansθmax = 49.9°, θmin = 2.1°
Absorption correction: multi-scan
Sheldrick (1996)
h = 2121
Tmin = 0.906, Tmax = 0.995k = 99
15033 measured reflectionsl = 2026
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)] = 0.061H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.170Calculated w = 1/[σ2(Fo2) + (0.087P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.002
8985 reflectionsΔρmax = 0.60 e Å3
164 parametersΔρmin = 0.47 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.35 (72)
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
O1A0.54349 (7)0.4792 (2)0.41500 (5)0.01780 (12)
N1A0.34977 (7)0.0829 (2)0.38307 (5)0.01534 (12)
H1A0.3046 (15)0.257 (4)0.3749 (13)0.023*
H2A0.2927 (16)0.040 (4)0.3755 (14)0.023*
H3A0.3887 (15)0.058 (5)0.4450 (12)0.023*
O2A0.69873 (6)0.1971 (2)0.34906 (6)0.02267 (14)
C1A0.57861 (8)0.2684 (2)0.36447 (6)0.01448 (14)
C2A0.46474 (8)0.0873 (2)0.31255 (6)0.01345 (12)
H4A0.4994 (6)0.114 (3)0.3029 (2)0.016*
C3A0.41773 (9)0.2111 (2)0.20576 (6)0.01788 (14)
H5A0.3832 (6)0.405 (3)0.2180 (2)0.021*
C4A0.53563 (14)0.2384 (5)0.13543 (10)0.0478 (5)
H6A0.6055 (12)0.355 (3)0.1690 (7)0.072*
H7A0.5042 (6)0.324 (3)0.0704 (10)0.072*
H8A0.5720 (11)0.053 (3)0.1223 (10)0.072*
C5A0.3010 (2)0.0419 (4)0.15395 (10)0.0433 (4)
H9A0.3342 (6)0.136 (3)0.1349 (3)0.052*
H100.2357 (11)0.0113 (7)0.2029 (9)0.052*
C6A0.23222 (14)0.1796 (4)0.05839 (9)0.0401 (3)
H110.1508 (13)0.069 (2)0.0352 (8)0.060*
H120.2961 (10)0.185 (3)0.0019 (8)0.060*
H130.2048 (14)0.375 (3)0.0757 (4)0.060*
O1B1.04247 (7)0.3207 (2)0.41788 (5)0.01882 (13)
N1B0.84594 (8)0.7006 (2)0.38644 (6)0.01696 (13)
H1B0.8049 (16)0.538 (5)0.3858 (13)0.025*
H2B0.7833 (16)0.843 (4)0.3679 (13)0.025*
H3B0.8731 (15)0.718 (4)0.4538 (12)0.025*
O2B1.19725 (7)0.5869 (2)0.34404 (6)0.02225 (14)
C1B1.07737 (8)0.5285 (2)0.36618 (6)0.01445 (13)
C2B0.96581 (8)0.7264 (2)0.32264 (7)0.01610 (14)
H4B0.9970 (6)0.908 (4)0.32651 (10)0.019*
C3B0.92580 (12)0.6565 (3)0.20954 (8)0.0302 (3)
H5B0.8594 (14)0.794 (2)0.1820 (4)0.045*
H6B0.8863 (13)0.468 (3)0.2053 (2)0.045*
H7B1.0061 (10)0.663 (3)0.1689 (6)0.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0174 (3)0.0160 (3)0.0195 (2)0.0005 (2)0.0027 (2)0.0030 (2)
N1A0.0116 (3)0.0173 (3)0.0168 (2)0.0020 (2)0.0014 (2)0.0023 (2)
O2A0.0109 (2)0.0187 (3)0.0382 (4)0.0004 (2)0.0002 (2)0.0004 (3)
C1A0.0118 (3)0.0129 (3)0.0184 (3)0.0011 (2)0.0022 (2)0.0015 (2)
C2A0.0113 (3)0.0126 (3)0.0163 (3)0.0001 (2)0.0006 (2)0.0003 (2)
C3A0.0177 (3)0.0195 (4)0.0162 (3)0.0021 (3)0.0012 (2)0.0015 (3)
C4A0.0303 (6)0.0918 (14)0.0220 (4)0.0037 (8)0.0083 (4)0.0122 (7)
C5A0.0533 (8)0.0441 (7)0.0292 (5)0.0276 (6)0.0240 (5)0.0141 (5)
C6A0.0371 (6)0.0577 (9)0.0237 (4)0.0052 (6)0.0132 (4)0.0061 (5)
O1B0.0171 (3)0.0153 (3)0.0238 (3)0.0002 (2)0.0009 (2)0.0036 (2)
N1B0.0116 (3)0.0165 (3)0.0226 (3)0.0014 (2)0.0009 (2)0.0019 (3)
O2B0.0114 (2)0.0198 (3)0.0357 (3)0.0004 (2)0.0028 (2)0.0016 (3)
C1B0.0114 (3)0.0132 (3)0.0184 (3)0.0002 (2)0.0019 (2)0.0017 (2)
C2B0.0128 (3)0.0154 (3)0.0199 (3)0.0004 (3)0.0011 (2)0.0021 (3)
C3B0.0261 (5)0.0457 (7)0.0183 (3)0.0038 (5)0.0030 (3)0.0018 (4)
Geometric parameters (Å, º) top
O1A—C1A1.2540 (11)C5A—H100.94 (2)
N1A—C2A1.4981 (11)C6A—H110.993 (13)
N1A—H1A0.94 (2)C6A—H120.993 (13)
N1A—H2A0.81 (2)C6A—H130.993 (13)
N1A—H3A0.87 (2)O1B—C1B1.2499 (11)
O2A—C1A1.2626 (11)N1B—C2B1.4882 (12)
C1A—C2A1.5383 (11)N1B—H1B0.87 (2)
C2A—C3A1.5443 (11)N1B—H2B0.94 (2)
C2A—H4A1.03 (2)N1B—H3B0.90 (2)
C3A—C4A1.5251 (15)O2B—C1B1.2669 (11)
C3A—C5A1.5275 (14)C1B—C2B1.5305 (12)
C3A—H5A1.00 (2)C2B—C3B1.5261 (13)
C4A—H6A0.967 (13)C2B—H4B0.92 (2)
C4A—H7A0.967 (13)C3B—H5B0.978 (11)
C4A—H8A0.967 (13)C3B—H6B0.978 (11)
C5A—C6A1.520 (2)C3B—H7B0.978 (11)
C5A—H9A0.94 (2)
C2A—N1A—H1A107.0 (10)C6A—C5A—H10108.55 (8)
C2A—N1A—H2A118.9 (12)C3A—C5A—H10108.55 (7)
H1A—N1A—H2A107.0 (15)H9A—C5A—H10107.5
C2A—N1A—H3A104.3 (10)C5A—C6A—H11109.47 (8)
H1A—N1A—H3A113.6 (17)C5A—C6A—H12109.47 (9)
H2A—N1A—H3A106.3 (18)H11—C6A—H12109.5
O1A—C1A—O2A126.00 (8)C5A—C6A—H13109.47 (10)
O1A—C1A—C2A116.94 (7)H11—C6A—H13109.5
O2A—C1A—C2A117.00 (8)H12—C6A—H13109.5
N1A—C2A—C1A107.83 (7)C2B—N1B—H1B117.0 (12)
N1A—C2A—C3A110.35 (6)C2B—N1B—H2B109.6 (11)
C1A—C2A—C3A110.54 (7)H1B—N1B—H2B109.5 (14)
N1A—C2A—H4A109.36 (5)C2B—N1B—H3B109.0 (10)
C1A—C2A—H4A109.36 (5)H1B—N1B—H3B101.8 (16)
C3A—C2A—H4A109.36 (5)H2B—N1B—H3B109.7 (16)
C4A—C3A—C5A111.65 (11)O1B—C1B—O2B125.76 (8)
C4A—C3A—C2A111.25 (8)O1B—C1B—C2B117.62 (7)
C5A—C3A—C2A111.78 (8)O2B—C1B—C2B116.59 (8)
C4A—C3A—H5A107.29 (10)N1B—C2B—C3B109.93 (7)
C5A—C3A—H5A107.29 (8)N1B—C2B—C1B109.11 (7)
C2A—C3A—H5A107.29 (5)C3B—C2B—C1B111.02 (8)
C3A—C4A—H6A109.47 (8)N1B—C2B—H4B108.92 (5)
C3A—C4A—H7A109.47 (6)C3B—C2B—H4B108.92 (7)
H6A—C4A—H7A109.5C1B—C2B—H4B108.92 (5)
C3A—C4A—H8A109.47 (10)C2B—C3B—H5B109.47 (6)
H6A—C4A—H8A109.5C2B—C3B—H6B109.47 (7)
H7A—C4A—H8A109.5H5B—C3B—H6B109.5
C6A—C5A—C3A114.85 (11)C2B—C3B—H7B109.47 (6)
C6A—C5A—H9A108.55 (10)H5B—C3B—H7B109.5
C3A—C5A—H9A108.55 (8)H6B—C3B—H7B109.5
O1A—C1A—C2A—N1A35.95 (10)C1A—C2A—C3A—C5A177.92 (10)
O2A—C1A—C2A—N1A146.62 (8)C4A—C3A—C5A—C6A65.3 (2)
O1A—C1A—C2A—C3A84.76 (9)C2A—C3A—C5A—C6A169.34 (12)
O2A—C1A—C2A—C3A92.67 (10)O1B—C1B—C2B—N1B23.75 (11)
N1A—C2A—C3A—C4A175.71 (12)O2B—C1B—C2B—N1B158.01 (8)
C1A—C2A—C3A—C4A56.51 (13)O1B—C1B—C2B—C3B97.55 (10)
N1A—C2A—C3A—C5A58.72 (12)O2B—C1B—C2B—C3B80.69 (11)
(L2) L-Isoleucine:D-aminobutyric acid top
Crystal data top
C6H13NO2·C4H9NO2F(000) = 512
Mr = 234.30Dx = 1.223 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
a = 26.9873 (6) ÅCell parameters from 8192 reflections
b = 4.7471 (1) ŵ = 0.09 mm1
c = 9.9652 (2) ÅT = 170 K
β = 94.546 (1)°Plate, colourless
V = 1272.64 (5) Å30.90 × 0.40 × 0.10 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
6238 independent reflections
Radiation source: fine-focus sealed tube5817 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
ω scansθmax = 39.1°, θmin = 2.1°
Absorption correction: multi-scan
Sheldrick (1996)
h = 4746
Tmin = 0.919, Tmax = 0.991k = 88
10909 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)] = 0.039Calculated w = 1/[σ2(Fo2) + (0.0467P)2 + 0.3251P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.104(Δ/σ)max = 0.002
S = 1.09Δρmax = 0.38 e Å3
6238 reflectionsΔρmin = 0.25 e Å3
177 parametersExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0139 (18)
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: 0.27 (59)
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
O1A0.20762 (2)0.18301 (14)0.54181 (6)0.01934 (11)
O2A0.17540 (3)0.1093 (2)0.68909 (6)0.02388 (12)
N1A0.19630 (2)0.2099 (2)0.34594 (6)0.01639 (11)
H1A0.1951 (5)0.059 (4)0.3046 (13)0.019 (3)*
H2A0.1898 (6)0.358 (4)0.2824 (15)0.034 (4)*
H3A0.2270 (5)0.247 (4)0.3859 (15)0.029 (4)*
C1A0.18363 (3)0.0317 (2)0.57158 (7)0.01544 (12)
C2A0.16044 (3)0.2075 (2)0.45311 (7)0.01488 (11)
H4A0.15508 (9)0.400 (3)0.4833 (5)0.018*
C3A0.11034 (3)0.0791 (2)0.39756 (8)0.01897 (13)
H5A0.11622 (10)0.109 (3)0.3763 (4)0.023*
C4A0.07301 (3)0.0813 (4)0.50479 (11)0.0500 (4)
H11A0.08726 (5)0.0108 (7)0.5846 (2)0.075*
H12A0.04338 (6)0.0164 (3)0.47158 (14)0.075*
H13A0.06489 (5)0.2724 (3)0.5257 (2)0.075*
C5A0.08951 (3)0.2255 (3)0.26779 (11)0.0329 (2)
H6A0.08468 (4)0.4241 (3)0.28667 (12)0.039*
H7A0.11391 (4)0.2122 (3)0.20133 (14)0.039*
C6A0.04046 (4)0.1025 (3)0.20776 (12)0.0392 (3)
H8A0.0317 (3)0.188 (2)0.1207 (12)0.059*
H9A0.0146 (3)0.141 (2)0.2674 (9)0.059*
H10A0.04393 (15)0.099 (2)0.1970 (12)0.059*
O1B0.21244 (2)0.98963 (14)1.04018 (6)0.02036 (11)
O2B0.18223 (3)0.7066 (2)1.19395 (6)0.02475 (13)
N1B0.19418 (3)0.6073 (2)0.84225 (6)0.01767 (11)
H1B0.1907 (5)0.792 (4)0.7976 (14)0.025 (3)*
H2B0.1844 (5)0.473 (4)0.7834 (14)0.026 (4)*
H3B0.2261 (5)0.578 (4)0.8696 (14)0.027 (3)*
C1B0.18923 (3)0.7767 (2)1.07458 (7)0.01622 (12)
C2B0.16422 (3)0.5946 (2)0.96181 (7)0.01621 (12)
H4B0.16252 (4)0.409 (3)0.9913 (5)0.019*
C3B0.11148 (3)0.7073 (2)0.92737 (10)0.0252 (2)
H5B0.0941 (2)0.7101 (2)1.0088 (10)0.030*
H6B0.11376 (4)0.900 (2)0.8963 (4)0.030*
C4B0.08096 (4)0.5386 (3)0.82100 (15)0.0420 (3)
H7B0.0469 (4)0.6303 (19)0.8023 (10)0.063*
H8B0.0766 (4)0.338 (2)0.8547 (6)0.063*
H9B0.0988 (3)0.534 (2)0.7345 (11)0.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0217 (2)0.0172 (3)0.0188 (2)0.0032 (2)0.0007 (2)0.0009 (2)
O2A0.0382 (3)0.0206 (3)0.0129 (2)0.0001 (2)0.0029 (2)0.0008 (2)
N1A0.0187 (2)0.0168 (3)0.0137 (2)0.0027 (2)0.0012 (2)0.0015 (2)
C1A0.0187 (3)0.0145 (3)0.0129 (2)0.0019 (2)0.0001 (2)0.0003 (2)
C2A0.0178 (3)0.0134 (3)0.0133 (2)0.0003 (2)0.0008 (2)0.0000 (2)
C3A0.0163 (3)0.0213 (3)0.0191 (3)0.0009 (2)0.0002 (2)0.0007 (3)
C4A0.0220 (4)0.0990 (12)0.0300 (4)0.0107 (6)0.0080 (3)0.0084 (7)
C5A0.0292 (4)0.0327 (5)0.0343 (4)0.0032 (4)0.0132 (3)0.0081 (4)
C6A0.0240 (4)0.0543 (7)0.0370 (5)0.0016 (4)0.0112 (3)0.0046 (5)
O1B0.0251 (3)0.0170 (3)0.0188 (2)0.0040 (2)0.0008 (2)0.0003 (2)
O2B0.0423 (3)0.0194 (3)0.0129 (2)0.0017 (3)0.0049 (2)0.0008 (2)
N1B0.0219 (3)0.0181 (3)0.0130 (2)0.0013 (2)0.0013 (2)0.0017 (2)
C1B0.0208 (3)0.0144 (3)0.0135 (2)0.0020 (2)0.0009 (2)0.0004 (2)
C2B0.0196 (3)0.0142 (3)0.0149 (2)0.0006 (2)0.0018 (2)0.0002 (2)
C3B0.0201 (3)0.0258 (4)0.0295 (4)0.0024 (3)0.0003 (3)0.0039 (3)
C4B0.0280 (4)0.0378 (6)0.0571 (7)0.0024 (4)0.0157 (4)0.0124 (6)
Geometric parameters (Å, º) top
O1A—C1A1.2558 (10)C6A—H8A0.970 (11)
O2A—C1A1.2640 (9)C6A—H9A0.970 (11)
N1A—C2A1.4971 (9)C6A—H10A0.970 (11)
N1A—H1A0.83 (2)O1B—C1B1.2512 (10)
N1A—H2A0.95 (2)O2B—C1B1.2637 (9)
N1A—H3A0.908 (15)N1B—C2B1.4931 (9)
C1A—C2A1.5376 (10)N1B—H1B0.98 (2)
C2A—C3A1.5451 (10)N1B—H2B0.89 (2)
C2A—H4A0.98 (2)N1B—H3B0.895 (14)
C3A—C4A1.5257 (12)C1B—C2B1.5315 (11)
C3A—C5A1.5350 (12)C2B—C3B1.5336 (11)
C3A—H5A0.94 (2)C2B—H4B0.93 (2)
C4A—H11A0.96C3B—C4B1.5184 (15)
C4A—H12A0.96C3B—H5B0.969 (11)
C4A—H13A0.96C3B—H6B0.969 (11)
C5A—C6A1.5248 (14)C4B—H7B1.021 (11)
C5A—H6A0.97C4B—H8B1.021 (11)
C5A—H7A0.97C4B—H9B1.021 (11)
C2A—N1A—H1A110.3 (9)C5A—C6A—H8A109.47 (7)
C2A—N1A—H2A112.5 (10)C5A—C6A—H9A109.47 (7)
H1A—N1A—H2A108.2 (13)H8A—C6A—H9A109.5
C2A—N1A—H3A107.9 (9)C5A—C6A—H10A109.47 (7)
H1A—N1A—H3A112.7 (14)H8A—C6A—H10A109.5
H2A—N1A—H3A105.1 (15)H9A—C6A—H10A109.5
O1A—C1A—O2A125.96 (7)C2B—N1B—H1B111.0 (8)
O1A—C1A—C2A116.44 (6)C2B—N1B—H2B110.2 (10)
O2A—C1A—C2A117.55 (7)H1B—N1B—H2B109.1 (13)
N1A—C2A—C1A107.76 (6)C2B—N1B—H3B108.7 (9)
N1A—C2A—C3A110.14 (6)H1B—N1B—H3B109.2 (15)
C1A—C2A—C3A110.64 (6)H2B—N1B—H3B108.6 (15)
N1A—C2A—H4A109.43 (4)O1B—C1B—O2B125.87 (8)
C1A—C2A—H4A109.43 (4)O1B—C1B—C2B117.14 (6)
C3A—C2A—H4A109.43 (5)O2B—C1B—C2B116.87 (7)
C4A—C3A—C5A111.65 (9)N1B—C2B—C1B109.13 (6)
C4A—C3A—C2A110.73 (7)N1B—C2B—C3B111.03 (6)
C5A—C3A—C2A112.02 (7)C1B—C2B—C3B108.33 (7)
C4A—C3A—H5A107.39 (8)N1B—C2B—H4B109.44 (5)
C5A—C3A—H5A107.39 (6)C1B—C2B—H4B109.44 (4)
C2A—C3A—H5A107.39 (5)C3B—C2B—H4B109.44 (5)
C3A—C4A—H11A109.47 (5)C4B—C3B—C2B114.49 (8)
C3A—C4A—H12A109.47 (6)C4B—C3B—H5B108.64 (7)
H11A—C4A—H12A109.5C2B—C3B—H5B108.64 (5)
C3A—C4A—H13A109.47 (8)C4B—C3B—H6B108.64 (7)
H11A—C4A—H13A109.5C2B—C3B—H6B108.64 (5)
H12A—C4A—H13A109.5H5B—C3B—H6B107.6
C6A—C5A—C3A113.94 (10)C3B—C4B—H7B109.47 (6)
C6A—C5A—H6A108.77 (8)C3B—C4B—H8B109.47 (7)
C3A—C5A—H6A108.77 (6)H7B—C4B—H8B109.5
C6A—C5A—H7A108.77 (6)C3B—C4B—H9B109.47 (7)
C3A—C5A—H7A108.8H7B—C4B—H9B109.5
H6A—C5A—H7A107.7H8B—C4B—H9B109.5
O1A—C1A—C2A—N1A37.92 (9)C4A—C3A—C5A—C6A56.15 (15)
O2A—C1A—C2A—N1A144.65 (7)C2A—C3A—C5A—C6A179.01 (9)
O1A—C1A—C2A—C3A82.53 (8)O1B—C1B—C2B—N1B31.73 (10)
O2A—C1A—C2A—C3A94.89 (9)O2B—C1B—C2B—N1B152.03 (7)
N1A—C2A—C3A—C4A178.73 (9)O1B—C1B—C2B—C3B89.27 (9)
C1A—C2A—C3A—C4A62.24 (10)O2B—C1B—C2B—C3B86.97 (9)
N1A—C2A—C3A—C5A53.38 (10)N1B—C2B—C3B—C4B62.94 (12)
C1A—C2A—C3A—C5A172.41 (7)C1B—C2B—C3B—C4B177.25 (9)
(L3) L-Isoleucine:D-Norvaline top
Crystal data top
C6H13NO2·C5H11NO2F(000) = 544
Mr = 248.32Dx = 1.225 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
a = 29.0557 (7) ÅCell parameters from 8192 reflections
b = 4.7551 (1) ŵ = 0.09 mm1
c = 9.9398 (2) ÅT = 150 K
β = 101.358 (1)°Plate, colourless
V = 1346.41 (5) Å30.65 × 0.60 × 0.20 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
6859 independent reflections
Radiation source: fine-focus sealed tube6684 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ω scansθmax = 40.4°, θmin = 3.9°
Absorption correction: multi-scan
Sheldrick (1996)
h = 5249
Tmin = 0.942, Tmax = 0.982k = 87
12203 measured reflectionsl = 1717
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)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097Calculated w = 1/[σ2(Fo2) + (0.048P)2 + 0.357P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
6859 reflectionsΔρmax = 0.59 e Å3
190 parametersΔρmin = 0.42 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.07 (45)
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
O1A0.20897 (2)0.14181 (12)0.52846 (5)0.01630 (9)
O2A0.17753 (2)0.14834 (13)0.66383 (5)0.01934 (10)
N1A0.20009 (2)0.24988 (13)0.32940 (5)0.01378 (8)
H1A0.1988 (5)0.094 (4)0.2874 (13)0.021 (3)*
H2A0.1954 (5)0.383 (3)0.2674 (14)0.023 (3)*
H3A0.2306 (5)0.291 (3)0.3772 (14)0.024 (3)*
C1A0.18622 (2)0.07260 (13)0.54954 (6)0.01264 (9)
C2A0.16555 (2)0.25143 (14)0.42301 (6)0.01207 (9)
H4A0.16119 (6)0.442 (3)0.4516 (4)0.014*
C3A0.11786 (2)0.13134 (15)0.34840 (6)0.01502 (10)
H5A0.12249 (7)0.066 (3)0.3310 (2)0.018*
C4A0.08169 (3)0.1502 (4)0.44034 (9)0.0405 (3)
H6A0.0946 (2)0.064 (3)0.5300 (11)0.061*
H7A0.0529 (4)0.050 (2)0.3969 (8)0.061*
H8A0.0741 (3)0.349 (2)0.4535 (10)0.061*
C5A0.10068 (3)0.2746 (2)0.20910 (9)0.0276 (2)
H9A0.09774 (4)0.482 (2)0.2246 (2)0.033*
H10A0.1250 (3)0.2480 (4)0.1512 (7)0.033*
C6A0.05388 (3)0.1654 (3)0.12998 (9)0.0309 (2)
H11A0.0475 (2)0.248 (2)0.0354 (11)0.046*
H12A0.0282 (3)0.221 (2)0.1788 (8)0.046*
H13A0.05511 (13)0.045 (2)0.1236 (10)0.046*
O1B0.21493 (2)1.02876 (11)1.02735 (5)0.01603 (9)
O2B0.18748 (2)0.74587 (13)1.17365 (5)0.01961 (10)
N1B0.19683 (2)0.64742 (13)0.82303 (5)0.01399 (8)
H1B0.1935 (5)0.831 (4)0.7834 (15)0.029 (4)*
H2B0.1873 (5)0.500 (3)0.7605 (14)0.022 (3)*
H3B0.2269 (5)0.628 (4)0.8636 (14)0.027 (3)*
C1B0.19343 (2)0.81508 (13)1.05548 (6)0.01264 (9)
C2B0.16937 (2)0.63188 (14)0.93505 (6)0.01266 (9)
H4B0.16855 (2)0.442 (3)0.9650 (4)0.015*
C3B0.11909 (2)0.7376 (2)0.88579 (7)0.01690 (10)
H5B0.1027 (2)0.7294 (2)0.9630 (7)0.020*
H6B0.12038 (3)0.9357 (19)0.8590 (3)0.020*
C4B0.09033 (3)0.5757 (2)0.76572 (10)0.0288 (2)
H7B0.08936 (3)0.385 (2)0.7896 (3)0.035*
H8B0.1051 (2)0.5885 (3)0.6901 (9)0.035*
C5B0.04021 (3)0.6876 (3)0.72515 (12)0.0334 (2)
H9B0.0230 (2)0.5782 (19)0.6468 (11)0.050*
H10B0.04104 (3)0.887 (2)0.6989 (11)0.050*
H11B0.0242 (2)0.669 (2)0.8036 (9)0.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0173 (2)0.0148 (2)0.0156 (2)0.00292 (15)0.0002 (2)0.0009 (2)
O2A0.0299 (2)0.0178 (2)0.0105 (2)0.0013 (2)0.0043 (2)0.0007 (2)
N1A0.0143 (2)0.0156 (2)0.0110 (2)0.0023 (2)0.00123 (15)0.0014 (2)
C1A0.0145 (2)0.0125 (2)0.0101 (2)0.0013 (2)0.0002 (2)0.0004 (2)
C2A0.0136 (2)0.0117 (2)0.0103 (2)0.0003 (2)0.0007 (2)0.0006 (2)
C3A0.0131 (2)0.0177 (3)0.0134 (2)0.0018 (2)0.0003 (2)0.0001 (2)
C4A0.0172 (3)0.0826 (9)0.0224 (3)0.0084 (4)0.0059 (3)0.0071 (5)
C5A0.0226 (3)0.0326 (4)0.0227 (3)0.0059 (3)0.0076 (3)0.0092 (3)
C6A0.0179 (3)0.0488 (5)0.0222 (3)0.0024 (3)0.0058 (2)0.0009 (4)
O1B0.0185 (2)0.0138 (2)0.0151 (2)0.00301 (15)0.0016 (2)0.0002 (2)
O2B0.0311 (3)0.0175 (2)0.0106 (2)0.0025 (2)0.0050 (2)0.0004 (2)
N1B0.0156 (2)0.0155 (2)0.0107 (2)0.0013 (2)0.00217 (15)0.0010 (2)
C1B0.0149 (2)0.0119 (2)0.0106 (2)0.0008 (2)0.0012 (2)0.0002 (2)
C2B0.0148 (2)0.0119 (2)0.0111 (2)0.0001 (2)0.0021 (2)0.0000 (2)
C3B0.0144 (2)0.0178 (3)0.0178 (2)0.0016 (2)0.0016 (2)0.0023 (2)
C4B0.0198 (3)0.0294 (4)0.0320 (4)0.0034 (3)0.0073 (3)0.0100 (3)
C5B0.0171 (3)0.0423 (5)0.0372 (4)0.0012 (3)0.0037 (3)0.0004 (4)
Geometric parameters (Å, º) top
O1A—C1A1.2551 (8)C6A—H13A1.002 (10)
O2A—C1A1.2636 (8)O1B—C1B1.2530 (8)
N1A—C2A1.4968 (8)O2B—C1B1.2640 (7)
N1A—H1A0.85 (2)N1B—C2B1.4938 (8)
N1A—H2A0.876 (15)N1B—H1B0.95 (2)
N1A—H3A0.939 (14)N1B—H2B0.941 (15)
C1A—C2A1.5388 (8)N1B—H3B0.892 (14)
C2A—C3A1.5464 (8)C1B—C2B1.5333 (9)
C2A—H4A0.966 (13)C2B—C3B1.5314 (9)
C3A—C4A1.5253 (10)C2B—H4B0.953 (13)
C3A—C5A1.5356 (10)C3B—C4B1.5240 (11)
C3A—H5A0.967 (14)C3B—H5B0.981 (9)
C4A—H6A0.985 (11)C3B—H6B0.981 (9)
C4A—H7A0.985 (11)C4B—C5B1.5279 (12)
C4A—H8A0.985 (11)C4B—H7B0.938 (11)
C5A—C6A1.5218 (11)C4B—H8B0.938 (11)
C5A—H9A1.004 (11)C5B—H9B0.987 (11)
C5A—H10A1.004 (11)C5B—H10B0.987 (11)
C6A—H11A1.002 (10)C5B—H11B0.987 (10)
C6A—H12A1.002 (10)
C2A—N1A—H1A109.9 (9)C5A—C6A—H13A109.47 (6)
C2A—N1A—H2A113.8 (9)H11A—C6A—H13A109.5
H1A—N1A—H2A107.5 (13)H12A—C6A—H13A109.5
C2A—N1A—H3A111.4 (8)C2B—N1B—H1B109.1 (9)
H1A—N1A—H3A112.1 (13)C2B—N1B—H2B108.9 (8)
H2A—N1A—H3A101.9 (13)H1B—N1B—H2B114.6 (12)
O1A—C1A—O2A125.92 (6)C2B—N1B—H3B106.1 (9)
O1A—C1A—C2A116.49 (5)H1B—N1B—H3B107.1 (15)
O2A—C1A—C2A117.54 (6)H2B—N1B—H3B110.8 (13)
N1A—C2A—C1A107.69 (5)O1B—C1B—O2B125.73 (6)
N1A—C2A—C3A110.31 (5)O1B—C1B—C2B117.20 (5)
C1A—C2A—C3A110.88 (5)O2B—C1B—C2B116.93 (6)
N1A—C2A—H4A109.31 (4)N1B—C2B—C3B111.18 (5)
C1A—C2A—H4A109.31 (3)N1B—C2B—C1B109.00 (5)
C3A—C2A—H4A109.31 (4)C3B—C2B—C1B108.82 (5)
C4A—C3A—C5A111.97 (7)N1B—C2B—H4B109.27 (4)
C4A—C3A—C2A110.43 (6)C3B—C2B—H4B109.27 (4)
C5A—C3A—C2A111.72 (6)C1B—C2B—H4B109.27 (3)
C4A—C3A—H5A107.49 (7)C4B—C3B—C2B115.22 (6)
C5A—C3A—H5A107.49 (5)C4B—C3B—H5B108.47 (5)
C2A—C3A—H5A107.49 (4)C2B—C3B—H5B108.47 (3)
C3A—C4A—H6A109.47 (5)C4B—C3B—H6B108.47 (5)
C3A—C4A—H7A109.47 (5)C2B—C3B—H6B108.47 (4)
H6A—C4A—H7A109.5H5B—C3B—H6B107.5
C3A—C4A—H8A109.47 (7)C3B—C4B—C5B112.21 (8)
H6A—C4A—H8A109.5C3B—C4B—H7B109.16 (5)
H7A—C4A—H8A109.5C5B—C4B—H7B109.16 (6)
C6A—C5A—C3A114.41 (7)C3B—C4B—H8B109.16 (5)
C6A—C5A—H9A108.66 (6)C5B—C4B—H8B109.16 (6)
C3A—C5A—H9A108.66 (5)H7B—C4B—H8B107.9
C6A—C5A—H10A108.66 (5)C4B—C5B—H9B109.47 (6)
C3A—C5A—H10A108.66 (4)C4B—C5B—H10B109.47 (6)
H9A—C5A—H10A107.6H9B—C5B—H10B109.5
C5A—C6A—H11A109.47 (5)C4B—C5B—H11B109.47 (6)
C5A—C6A—H12A109.47 (6)H9B—C5B—H11B109.5
H11A—C6A—H12A109.5H10B—C5B—H11B109.5
O1A—C1A—C2A—N1A36.77 (7)C2A—C3A—C5A—C6A179.85 (8)
O2A—C1A—C2A—N1A145.56 (6)O1B—C1B—C2B—N1B31.33 (8)
O1A—C1A—C2A—C3A84.01 (7)O2B—C1B—C2B—N1B152.66 (6)
O2A—C1A—C2A—C3A93.66 (7)O1B—C1B—C2B—C3B90.08 (7)
N1A—C2A—C3A—C4A176.34 (8)O2B—C1B—C2B—C3B85.93 (7)
C1A—C2A—C3A—C4A64.45 (9)N1B—C2B—C3B—C4B60.00 (9)
N1A—C2A—C3A—C5A51.02 (8)C1B—C2B—C3B—C4B179.93 (7)
C1A—C2A—C3A—C5A170.23 (6)C2B—C3B—C4B—C5B178.31 (8)
C4A—C3A—C5A—C6A55.69 (12)
(L4) L-Isoleucine:D-Norleucine top
Crystal data top
C12H26N2O4F(000) = 576
Mr = 262.35Dx = 1.228 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 10.012 (2) ÅCell parameters from 8192 reflections
b = 4.7227 (9) ŵ = 0.09 mm1
c = 30.335 (6) ÅT = 150 K
β = 98.38 (3)°Plate, colourless
V = 1419.1 (5) Å30.55 × 0.30 × 0.15 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
14651 independent reflections
Radiation source: fine-focus sealed tube12393 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ω scansθmax = 40.4°, θmin = 3.4°
Absorption correction: multi-scan
Sheldrick (1996)
h = 1813
Tmin = 0.951, Tmax = 0.986k = 88
25110 measured reflectionsl = 5449
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)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118Calculated w = 1/[σ2(Fo2) + (0.0427P)2 + 0.2719P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.008
14651 reflectionsΔρmax = 0.51 e Å3
399 parametersΔρmin = 0.26 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.21 (58)
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
O1A0.57731 (8)0.3733 (2)0.03982 (3)0.01622 (15)
O2A0.73624 (7)0.6764 (2)0.07098 (3)0.0190 (2)
N1A0.37984 (8)0.7489 (2)0.04661 (3)0.01321 (15)
H1A0.3439 (18)0.591 (5)0.0473 (6)0.024 (5)*
H2A0.3208 (16)0.886 (4)0.0510 (5)0.017 (4)*
H3A0.3986 (16)0.787 (4)0.0176 (6)0.024 (4)*
C1A0.61585 (10)0.5921 (2)0.06153 (3)0.0126 (2)
C2A0.50558 (9)0.7649 (3)0.07982 (3)0.0120 (2)
H4A0.5331 (5)0.953 (4)0.08317 (7)0.014*
C3A0.48050 (10)0.6476 (3)0.12537 (3)0.0146 (2)
H5A0.4680 (2)0.442 (4)0.12249 (6)0.018*
C4A0.60488 (12)0.7028 (4)0.16009 (4)0.0321 (4)
H6A0.6145 (8)0.902 (3)0.1653 (3)0.048*
H7A0.6835 (10)0.632 (3)0.1493 (2)0.048*
H8A0.5942 (6)0.609 (3)0.1873 (4)0.048*
C5A0.35324 (11)0.7742 (3)0.14042 (4)0.0205 (2)
H9A0.3627 (2)0.979 (3)0.14180 (4)0.025*
H10A0.2763 (9)0.7308 (6)0.1181 (3)0.025*
C6A0.32446 (12)0.6672 (3)0.18558 (4)0.0266 (2)
H11A0.3267 (12)0.469 (2)0.18591 (14)0.040*
H12A0.2391 (11)0.729 (2)0.1904 (2)0.040*
H13A0.3899 (10)0.737 (2)0.2081 (3)0.040*
O1B0.06680 (8)0.3525 (2)0.46575 (3)0.01550 (15)
O2B0.23338 (7)0.6571 (2)0.44202 (3)0.0189 (2)
N1B0.12231 (8)0.7276 (2)0.44920 (3)0.0133 (2)
H1B0.1562 (19)0.567 (5)0.4464 (6)0.027 (5)*
H2B0.1737 (16)0.870 (4)0.4416 (6)0.015 (4)*
H3B0.1147 (19)0.764 (5)0.4817 (7)0.041 (5)*
C1B0.11286 (10)0.5720 (2)0.44573 (3)0.0118 (2)
C2B0.01456 (9)0.7441 (2)0.42180 (3)0.0113 (2)
H4B0.0425 (5)0.932 (4)0.41990 (5)0.014*
C3B0.01275 (10)0.6275 (3)0.37431 (3)0.0148 (2)
H5B0.0019 (3)0.423 (4)0.37650 (5)0.018*
C4B0.14991 (12)0.6797 (4)0.34603 (4)0.0359 (4)
H6B0.1635 (6)0.880 (3)0.3416 (4)0.054*
H7B0.2203 (9)0.604 (3)0.3611 (3)0.054*
H8B0.1523 (5)0.588 (3)0.3175 (4)0.054*
C5B0.10115 (11)0.7570 (3)0.35235 (3)0.0207 (2)
H9B0.0884 (2)0.961 (3)0.35056 (4)0.025*
H10B0.1866 (10)0.7210 (5)0.3712 (2)0.025*
C6B0.10985 (12)0.6438 (3)0.30581 (4)0.0250 (2)
H11B0.1158 (11)0.438 (2)0.30679 (8)0.038*
H12B0.1896 (11)0.721 (2)0.2953 (2)0.038*
H13B0.0297 (10)0.700 (2)0.2857 (2)0.038*
O1C0.06759 (8)0.5400 (2)0.03168 (3)0.01510 (14)
O2C0.23620 (7)0.2430 (2)0.05654 (3)0.01771 (15)
N1C0.12253 (8)0.1766 (2)0.05200 (3)0.0129 (2)
H1C0.1598 (17)0.341 (4)0.0561 (6)0.018 (4)*
H2C0.181 (2)0.041 (5)0.0608 (7)0.032 (5)*
H3C0.1220 (14)0.149 (4)0.0222 (5)0.015 (3)*
C1C0.11430 (10)0.3220 (2)0.05172 (3)0.0119 (2)
C2C0.01808 (9)0.1480 (2)0.07577 (3)0.0117 (2)
H4C0.0442 (5)0.046 (4)0.07606 (3)0.014*
C3C0.03029 (10)0.2567 (3)0.12376 (3)0.0156 (2)
H5C0.1178 (11)0.2265 (4)0.1374 (2)0.019*
H6C0.0160 (2)0.450 (2)0.12287 (3)0.019*
C4C0.06530 (11)0.1248 (3)0.15284 (3)0.0188 (2)
H7C0.1562 (11)0.1779 (7)0.14159 (14)0.023*
H8C0.05917 (13)0.077 (3)0.15141 (4)0.023*
C5C0.03172 (12)0.2200 (3)0.20110 (3)0.0252 (2)
H9C0.02596 (15)0.424 (3)0.20195 (4)0.030*
H10C0.0555 (11)0.1459 (10)0.2133 (2)0.030*
C6C0.13517 (13)0.1242 (4)0.23011 (4)0.0290 (3)
H11C0.1050 (7)0.178 (2)0.2608 (3)0.043*
H12C0.1450 (9)0.080 (2)0.2282 (3)0.043*
H13C0.2214 (10)0.213 (2)0.2198 (3)0.043*
O1D0.42787 (8)0.5241 (2)0.46106 (3)0.01604 (15)
O2D0.26720 (7)0.2234 (2)0.43081 (3)0.0177 (2)
N1D0.62596 (8)0.1515 (2)0.45482 (3)0.0139 (2)
H1D0.6611 (16)0.327 (4)0.4528 (5)0.016 (4)*
H2D0.687 (2)0.018 (5)0.4478 (6)0.031 (5)*
H3D0.6124 (16)0.124 (5)0.4847 (6)0.026 (4)*
C1D0.38825 (10)0.3031 (2)0.44027 (3)0.0122 (2)
C2D0.49752 (9)0.1216 (3)0.42342 (3)0.0122 (2)
H4D0.4708 (5)0.067 (4)0.42251 (4)0.015*
C3D0.52239 (10)0.2135 (3)0.37671 (3)0.0163 (2)
H5D0.5325 (2)0.413 (2)0.37625 (3)0.020*
H6D0.6042 (10)0.1315 (10)0.37055 (8)0.020*
C4D0.40807 (11)0.1269 (3)0.34040 (3)0.0215 (2)
H7D0.3249 (10)0.1967 (9)0.34805 (10)0.026*
H8D0.40265 (13)0.075 (3)0.33955 (4)0.026*
C5D0.42415 (12)0.2348 (3)0.29394 (4)0.0258 (2)
H9D0.3457 (10)0.1742 (8)0.2729 (3)0.031*
H10D0.42458 (12)0.442 (3)0.29441 (4)0.031*
C6D0.55160 (13)0.1324 (4)0.27712 (4)0.0343 (3)
H11D0.6301 (10)0.216 (2)0.2951 (4)0.052*
H12D0.5493 (6)0.189 (3)0.2462 (4)0.052*
H13D0.5569 (7)0.073 (3)0.2793 (4)0.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0166 (3)0.0156 (4)0.0173 (3)0.0006 (3)0.0054 (3)0.0029 (3)
O2A0.0104 (3)0.0182 (4)0.0290 (4)0.0010 (3)0.0054 (3)0.0001 (3)
N1A0.0110 (3)0.0145 (4)0.0144 (3)0.0013 (3)0.0030 (2)0.0021 (3)
C1A0.0117 (4)0.0119 (4)0.0149 (4)0.0013 (3)0.0047 (3)0.0018 (3)
C2A0.0098 (3)0.0119 (4)0.0146 (3)0.0002 (3)0.0032 (3)0.0006 (3)
C3A0.0137 (4)0.0164 (4)0.0140 (3)0.0008 (4)0.0031 (3)0.0004 (4)
C4A0.0186 (4)0.0600 (11)0.0169 (4)0.0019 (6)0.0003 (3)0.0016 (6)
C5A0.0192 (4)0.0245 (5)0.0199 (4)0.0027 (4)0.0098 (3)0.0010 (4)
C6A0.0250 (5)0.0404 (7)0.0162 (4)0.0048 (5)0.0090 (3)0.0015 (5)
O1B0.0161 (3)0.0147 (4)0.0163 (3)0.0005 (3)0.0046 (3)0.0031 (3)
O2B0.0109 (3)0.0178 (4)0.0294 (4)0.0007 (3)0.0075 (3)0.0011 (4)
N1B0.0099 (3)0.0153 (4)0.0149 (3)0.0011 (3)0.0025 (2)0.0015 (3)
C1B0.0111 (4)0.0115 (4)0.0135 (3)0.0013 (3)0.0042 (3)0.0018 (3)
C2B0.0090 (3)0.0113 (4)0.0140 (3)0.0001 (3)0.0028 (3)0.0009 (3)
C3B0.0135 (3)0.0177 (4)0.0133 (3)0.0016 (4)0.0029 (3)0.0009 (4)
C4B0.0170 (4)0.0717 (11)0.0182 (4)0.0009 (6)0.0001 (3)0.0027 (6)
C5B0.0216 (4)0.0261 (5)0.0157 (4)0.0065 (5)0.0079 (3)0.0027 (4)
C6B0.0224 (5)0.0379 (6)0.0159 (4)0.0006 (5)0.0067 (3)0.0013 (5)
O1C0.0151 (3)0.0138 (3)0.0171 (3)0.0011 (3)0.0043 (2)0.0025 (3)
O2C0.0103 (3)0.0162 (4)0.0276 (4)0.0015 (3)0.0059 (2)0.0019 (3)
N1C0.0103 (3)0.0149 (4)0.0138 (3)0.0014 (3)0.0027 (2)0.0010 (3)
C1C0.0108 (3)0.0122 (4)0.0132 (3)0.0007 (3)0.0034 (3)0.0014 (3)
C2C0.0104 (3)0.0116 (4)0.0136 (3)0.0003 (3)0.0033 (3)0.0002 (3)
C3C0.0153 (4)0.0186 (5)0.0134 (3)0.0030 (4)0.0033 (3)0.0015 (4)
C4C0.0191 (4)0.0237 (5)0.0147 (4)0.0035 (4)0.0057 (3)0.0011 (4)
C5C0.0251 (5)0.0370 (6)0.0144 (4)0.0053 (5)0.0060 (3)0.0031 (4)
C6C0.0280 (5)0.0445 (7)0.0161 (4)0.0034 (6)0.0087 (4)0.0005 (5)
O1D0.0164 (3)0.0137 (3)0.0186 (3)0.0005 (3)0.0046 (3)0.0035 (3)
O2D0.0106 (3)0.0179 (4)0.0253 (3)0.0007 (3)0.0049 (2)0.0024 (3)
N1D0.0108 (3)0.0149 (4)0.0163 (3)0.0016 (3)0.0027 (2)0.0015 (3)
C1D0.0110 (3)0.0130 (4)0.0132 (3)0.0002 (3)0.0040 (3)0.0013 (3)
C2D0.0108 (3)0.0118 (4)0.0144 (3)0.0001 (4)0.0031 (3)0.0004 (3)
C3D0.0138 (4)0.0217 (5)0.0142 (3)0.0012 (4)0.0051 (3)0.0008 (4)
C4D0.0161 (4)0.0328 (6)0.0159 (4)0.0026 (4)0.0035 (3)0.0000 (4)
C5D0.0227 (5)0.0398 (7)0.0154 (4)0.0013 (5)0.0039 (3)0.0017 (4)
C6D0.0265 (5)0.0592 (9)0.0191 (4)0.0020 (6)0.0093 (4)0.0048 (6)
Geometric parameters (Å, º) top
O1A—C1A1.2557 (14)O1C—C1C1.2511 (14)
O2A—C1A1.2620 (13)O2C—C1C1.2642 (12)
N1A—C2A1.4954 (13)N1C—C2C1.4915 (13)
N1A—H1A0.83 (2)N1C—H1C0.88 (2)
N1A—H2A0.90 (2)N1C—H2C0.93 (2)
N1A—H3A0.94 (2)N1C—H3C0.915 (15)
C1A—C2A1.5398 (14)C1C—C2C1.5297 (14)
C2A—C3A1.5429 (14)C2C—C3C1.5315 (14)
C2A—H4A0.93 (2)C2C—H4C0.95 (2)
C3A—C4A1.532 (2)C3C—C4C1.5256 (15)
C3A—C5A1.5357 (14)C3C—H5C0.924 (11)
C3A—H5A0.98 (2)C3C—H6C0.924 (11)
C4A—H6A0.956 (12)C4C—C5C1.522 (2)
C4A—H7A0.956 (12)C4C—H7C0.958 (11)
C4A—H8A0.956 (12)C4C—H8C0.958 (12)
C5A—C6A1.526 (2)C5C—C6C1.522 (2)
C5A—H9A0.970 (12)C5C—H9C0.963 (12)
C5A—H10A0.970 (12)C5C—H10C0.963 (12)
C6A—H11A0.935 (10)C6C—H11C0.970 (11)
C6A—H12A0.935 (10)C6C—H12C0.970 (11)
C6A—H13A0.935 (10)C6C—H13C0.970 (11)
O1B—C1B1.2549 (14)O1D—C1D1.2534 (14)
O2B—C1B1.2613 (12)O2D—C1D1.2616 (12)
N1B—C2B1.4977 (13)N1D—C2D1.4915 (14)
N1B—H1B0.84 (2)N1D—H1D0.90 (2)
N1B—H2B0.90 (2)N1D—H2D0.92 (2)
N1B—H3B1.02 (2)N1D—H3D0.95 (2)
C1B—C2B1.5376 (14)C1D—C2D1.5352 (14)
C2B—C3B1.5448 (14)C2D—C3D1.5364 (14)
C2B—H4B0.93 (2)C2D—H4D0.93 (2)
C3B—C4B1.529 (2)C3D—C4D1.524 (2)
C3B—C5B1.5296 (15)C3D—H5D0.949 (12)
C3B—H5B0.98 (2)C3D—H6D0.949 (11)
C4B—H6B0.964 (13)C4D—C5D1.529 (2)
C4B—H7B0.964 (13)C4D—H7D0.956 (12)
C4B—H8B0.964 (12)C4D—H8D0.956 (12)
C5B—C6B1.524 (2)C5D—C6D1.521 (2)
C5B—H9B0.973 (12)C5D—H9D0.980 (12)
C5B—H10B0.973 (12)C5D—H10D0.980 (12)
C6B—H11B0.972 (11)C6D—H11D0.972 (12)
C6B—H12B0.972 (11)C6D—H12D0.972 (12)
C6B—H13B0.972 (10)C6D—H13D0.972 (12)
C2A—N1A—H1A110.8 (13)C2C—N1C—H1C113.8 (11)
C2A—N1A—H2A111.8 (11)C2C—N1C—H2C112.6 (12)
H1A—N1A—H2A110.3 (15)H1C—N1C—H2C105.8 (16)
C2A—N1A—H3A110.9 (10)C2C—N1C—H3C108.9 (9)
H1A—N1A—H3A109.8 (17)H1C—N1C—H3C109.1 (15)
H2A—N1A—H3A103.0 (15)H2C—N1C—H3C106.4 (16)
O1A—C1A—O2A126.08 (10)O1C—C1C—O2C125.82 (10)
O1A—C1A—C2A116.32 (9)O1C—C1C—C2C117.19 (9)
O2A—C1A—C2A117.55 (9)O2C—C1C—C2C116.79 (9)
N1A—C2A—C1A107.94 (8)N1C—C2C—C1C109.67 (8)
N1A—C2A—C3A110.76 (8)N1C—C2C—C3C111.61 (8)
C1A—C2A—C3A110.56 (9)C1C—C2C—C3C107.75 (9)
N1A—C2A—H4A109.18 (6)N1C—C2C—H4C109.26 (6)
C1A—C2A—H4A109.18 (6)C1C—C2C—H4C109.26 (6)
C3A—C2A—H4A109.18 (6)C3C—C2C—H4C109.26 (6)
C4A—C3A—C5A110.86 (9)C4C—C3C—C2C116.28 (9)
C4A—C3A—C2A109.43 (9)C4C—C3C—H5C108.22 (6)
C5A—C3A—C2A112.13 (9)C2C—C3C—H5C108.22 (6)
C4A—C3A—H5A108.09 (9)C4C—C3C—H6C108.22 (7)
C5A—C3A—H5A108.09 (6)C2C—C3C—H6C108.22 (6)
C2A—C3A—H5A108.09 (6)H5C—C3C—H6C107.4
C3A—C4A—H6A109.47 (9)C5C—C4C—C3C111.50 (10)
C3A—C4A—H7A109.47 (7)C5C—C4C—H7C109.33 (7)
H6A—C4A—H7A109.5C3C—C4C—H7C109.33 (6)
C3A—C4A—H8A109.47 (7)C5C—C4C—H8C109.33 (8)
H6A—C4A—H8A109.5C3C—C4C—H8C109.33 (7)
H7A—C4A—H8A109.5H7C—C4C—H8C108.0
C6A—C5A—C3A114.27 (10)C4C—C5C—C6C113.26 (10)
C6A—C5A—H9A108.69 (7)C4C—C5C—H9C108.92 (7)
C3A—C5A—H9A108.69 (6)C6C—C5C—H9C108.92 (8)
C6A—C5A—H10A108.69 (7)C4C—C5C—H10C108.92 (7)
C3A—C5A—H10A108.69 (6)C6C—C5C—H10C108.92 (7)
H9A—C5A—H10A107.6H9C—C5C—H10C107.7
C5A—C6A—H11A109.47 (7)C5C—C6C—H11C109.47 (7)
C5A—C6A—H12A109.47 (7)C5C—C6C—H12C109.47 (8)
H11A—C6A—H12A109.5H11C—C6C—H12C109.5
C5A—C6A—H13A109.47 (7)C5C—C6C—H13C109.47 (8)
H11A—C6A—H13A109.5H11C—C6C—H13C109.5
H12A—C6A—H13A109.5H12C—C6C—H13C109.5
C2B—N1B—H1B110.0 (13)C2D—N1D—H1D110.6 (10)
C2B—N1B—H2B109.4 (10)C2D—N1D—H2D108.9 (12)
H1B—N1B—H2B113.2 (15)H1D—N1D—H2D109.5 (16)
C2B—N1B—H3B109.8 (11)C2D—N1D—H3D111.6 (10)
H1B—N1B—H3B109.7 (18)H1D—N1D—H3D107.7 (16)
H2B—N1B—H3B104.7 (16)H2D—N1D—H3D108.6 (16)
O1B—C1B—O2B125.86 (10)O1D—C1D—O2D125.87 (10)
O1B—C1B—C2B116.72 (9)O1D—C1D—C2D116.35 (9)
O2B—C1B—C2B117.35 (9)O2D—C1D—C2D117.73 (9)
N1B—C2B—C1B107.91 (8)N1D—C2D—C1D108.92 (8)
N1B—C2B—C3B111.40 (8)N1D—C2D—C3D108.77 (8)
C1B—C2B—C3B110.32 (9)C1D—C2D—C3D111.61 (9)
N1B—C2B—H4B109.06 (6)N1D—C2D—H4D109.17 (6)
C1B—C2B—H4B109.06 (6)C1D—C2D—H4D109.17 (6)
C3B—C2B—H4B109.06 (6)C3D—C2D—H4D109.17 (7)
C4B—C3B—C5B110.90 (10)C4D—C3D—C2D112.64 (9)
C4B—C3B—C2B109.53 (9)C4D—C3D—H5D109.07 (8)
C5B—C3B—C2B112.00 (9)C2D—C3D—H5D109.07 (7)
C4B—C3B—H5B108.10 (9)C4D—C3D—H6D109.07 (6)
C5B—C3B—H5B108.10 (7)C2D—C3D—H6D109.07 (6)
C2B—C3B—H5B108.10 (6)H5D—C3D—H6D107.8
C3B—C4B—H6B109.47 (9)C3D—C4D—C5D114.06 (10)
C3B—C4B—H7B109.47 (7)C3D—C4D—H7D108.74 (6)
H6B—C4B—H7B109.5C5D—C4D—H7D108.74 (7)
C3B—C4B—H8B109.47 (7)C3D—C4D—H8D108.74 (8)
H6B—C4B—H8B109.5C5D—C4D—H8D108.74 (8)
H7B—C4B—H8B109.5H7D—C4D—H8D107.6
C6B—C5B—C3B114.22 (10)C6D—C5D—C4D114.16 (11)
C6B—C5B—H9B108.70 (8)C6D—C5D—H9D108.72 (7)
C3B—C5B—H9B108.70 (7)C4D—C5D—H9D108.72 (7)
C6B—C5B—H10B108.70 (7)C6D—C5D—H10D108.72 (9)
C3B—C5B—H10B108.70 (6)C4D—C5D—H10D108.72 (8)
H9B—C5B—H10B107.6H9D—C5D—H10D107.6
C5B—C6B—H11B109.47 (8)C5D—C6D—H11D109.47 (7)
C5B—C6B—H12B109.47 (7)C5D—C6D—H12D109.47 (7)
H11B—C6B—H12B109.5H11D—C6D—H12D109.5
C5B—C6B—H13B109.47 (7)C5D—C6D—H13D109.47 (9)
H11B—C6B—H13B109.5H11D—C6D—H13D109.5
H12B—C6B—H13B109.5H12D—C6D—H13D109.5
O1A—C1A—C2A—N1A35.32 (12)C4B—C3B—C5B—C6B58.8 (2)
O2A—C1A—C2A—N1A147.19 (9)C2B—C3B—C5B—C6B178.53 (10)
O1A—C1A—C2A—C3A85.98 (11)O1C—C1C—C2C—N1C30.36 (13)
O2A—C1A—C2A—C3A91.51 (12)O2C—C1C—C2C—N1C154.44 (9)
N1A—C2A—C3A—C4A172.54 (11)O1C—C1C—C2C—C3C91.31 (11)
C1A—C2A—C3A—C4A67.85 (13)O2C—C1C—C2C—C3C83.88 (12)
N1A—C2A—C3A—C5A49.09 (13)N1C—C2C—C3C—C4C55.33 (13)
C1A—C2A—C3A—C5A168.70 (9)C1C—C2C—C3C—C4C175.79 (10)
C4A—C3A—C5A—C6A56.81 (15)C2C—C3C—C4C—C5C172.52 (10)
C2A—C3A—C5A—C6A179.45 (10)C3C—C4C—C5C—C6C172.61 (11)
O1B—C1B—C2B—N1B35.53 (12)O1D—C1D—C2D—N1D31.26 (12)
O2B—C1B—C2B—N1B147.28 (9)O2D—C1D—C2D—N1D151.10 (9)
O1B—C1B—C2B—C3B86.38 (11)O1D—C1D—C2D—C3D88.85 (11)
O2B—C1B—C2B—C3B90.81 (12)O2D—C1D—C2D—C3D88.79 (12)
N1B—C2B—C3B—C4B173.53 (11)N1D—C2D—C3D—C4D166.58 (10)
C1B—C2B—C3B—C4B66.65 (13)C1D—C2D—C3D—C4D73.23 (13)
N1B—C2B—C3B—C5B50.06 (13)C2D—C3D—C4D—C5D175.50 (11)
C1B—C2B—C3B—C5B169.88 (9)C3D—C4D—C5D—C6D59.9 (2)
(L5) L-Isoleucine:D-Methionine top
Crystal data top
C11H24N2O4SF(000) = 608
Mr = 280.38Dx = 1.292 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
a = 31.7681 (3) ÅCell parameters from 8192 reflections
b = 4.7170 (1) ŵ = 0.23 mm1
c = 10.0043 (1) ÅT = 150 K
β = 105.914 (1)°Plate, colourless
V = 1441.69 (4) Å30.70 × 0.25 × 0.10 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
10115 independent reflections
Radiation source: fine-focus sealed tube8127 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 49.7°, θmin = 2.1°
Absorption correction: multi-scan
Sheldrick (1996)
h = 6065
Tmin = 0.849, Tmax = 0.977k = 97
18678 measured reflectionsl = 2021
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)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103Calculated w = 1/[σ2(Fo2) + (0.0408P)2 + 0.0836P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.002
10115 reflectionsΔρmax = 0.39 e Å3
199 parametersΔρmin = 0.41 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
O1A0.21236 (2)0.04905 (13)0.52140 (6)0.01519 (9)
O2A0.18353 (2)0.25353 (14)0.64543 (6)0.01743 (10)
N1A0.20339 (2)0.3287 (2)0.31447 (6)0.01293 (9)
H1A0.2021 (5)0.157 (4)0.2730 (16)0.023 (4)*
H2A0.1972 (5)0.469 (4)0.2451 (16)0.022 (4)*
H3A0.2302 (5)0.351 (4)0.3692 (15)0.021 (3)*
C1A0.19126 (2)0.16935 (14)0.53428 (7)0.01131 (10)
C2A0.17168 (2)0.3419 (2)0.40076 (6)0.01124 (9)
H4A0.16835 (6)0.528 (3)0.4242 (4)0.013*
C3A0.12662 (2)0.2209 (2)0.32049 (7)0.01389 (10)
H5A0.12979 (6)0.005 (4)0.31350 (14)0.017*
C4A0.09334 (3)0.2784 (3)0.40277 (10)0.0296 (2)
H6A0.1054 (2)0.212 (3)0.4999 (12)0.044*
H7A0.0658 (4)0.175 (2)0.3592 (9)0.044*
H8A0.0873 (3)0.485 (3)0.4025 (11)0.044*
C5A0.11051 (3)0.3393 (2)0.17198 (8)0.01999 (13)
H9A0.10841 (4)0.555 (2)0.17695 (9)0.024*
H10A0.1330 (3)0.2926 (6)0.1195 (6)0.024*
C6A0.06593 (3)0.2217 (3)0.09035 (10)0.0284 (2)
H11A0.0605 (2)0.270 (2)0.0063 (12)0.043*
H12A0.0434 (3)0.302 (2)0.1260 (9)0.043*
H13A0.06588 (13)0.019 (2)0.1001 (10)0.043*
S1B0.049904 (7)0.85919 (7)0.63701 (2)0.02460 (5)
O1B0.21691 (2)1.12247 (13)1.02232 (6)0.01442 (9)
O2B0.19106 (2)0.82313 (14)1.15532 (5)0.01765 (10)
N1B0.20126 (2)0.75061 (14)0.80964 (6)0.01227 (9)
H1B0.1996 (5)0.923 (4)0.7673 (16)0.024 (4)*
H2B0.1915 (5)0.622 (4)0.7417 (16)0.023 (4)*
H3B0.2286 (5)0.722 (4)0.8599 (16)0.025 (4)*
C1B0.19685 (2)0.90354 (14)1.04098 (6)0.01108 (9)
C2B0.17469 (2)0.7287 (2)0.91168 (6)0.01114 (9)
H4B0.17296 (4)0.534 (3)0.9375 (4)0.013*
C3B0.12835 (2)0.8464 (2)0.85005 (7)0.01527 (10)
H5B0.1117 (2)0.8176 (4)0.9157 (7)0.018*
H6B0.13027 (3)1.047 (2)0.8366 (2)0.018*
C4B0.10391 (3)0.7110 (2)0.71200 (9)0.02069 (14)
H7B0.10098 (4)0.504 (3)0.7266 (2)0.025*
H8B0.1216 (2)0.7351 (4)0.6447 (8)0.025*
C5B0.01913 (4)0.6806 (3)0.73896 (13)0.0339 (2)
H9B0.0106 (4)0.731 (2)0.7061 (10)0.051*
H10B0.0298 (3)0.735 (2)0.8327 (12)0.051*
H11B0.0221 (3)0.483 (3)0.7313 (11)0.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0183 (2)0.0132 (2)0.0132 (2)0.0035 (2)0.0027 (2)0.0016 (2)
O2A0.0279 (3)0.0160 (2)0.0092 (2)0.0013 (2)0.0065 (2)0.0004 (2)
N1A0.0153 (2)0.0136 (2)0.0098 (2)0.0021 (2)0.00333 (15)0.0009 (2)
C1A0.0146 (2)0.0102 (2)0.0084 (2)0.0009 (2)0.0017 (2)0.0001 (2)
C2A0.0148 (2)0.0100 (2)0.0087 (2)0.0000 (2)0.0028 (2)0.0000 (2)
C3A0.0146 (2)0.0148 (3)0.0112 (2)0.0006 (2)0.0017 (2)0.0001 (2)
C4A0.0165 (3)0.0534 (7)0.0201 (3)0.0014 (3)0.0069 (3)0.0047 (4)
C5A0.0201 (3)0.0229 (3)0.0132 (2)0.0002 (3)0.0017 (2)0.0027 (3)
C6A0.0203 (4)0.0401 (6)0.0192 (3)0.0008 (4)0.0039 (3)0.0014 (4)
S1B0.01464 (7)0.03396 (12)0.02131 (8)0.00098 (8)0.00164 (6)0.00555 (9)
O1B0.0166 (2)0.0125 (2)0.0131 (2)0.0035 (2)0.0024 (2)0.0004 (2)
O2B0.0298 (3)0.0149 (2)0.0093 (2)0.0022 (2)0.0070 (2)0.0001 (2)
N1B0.0138 (2)0.0140 (2)0.0089 (2)0.0012 (2)0.0030 (2)0.0009 (2)
C1B0.0134 (2)0.0112 (3)0.0083 (2)0.0006 (2)0.0022 (2)0.0004 (2)
C2B0.0137 (2)0.0107 (2)0.0086 (2)0.0009 (2)0.0025 (2)0.0008 (2)
C3B0.0128 (2)0.0176 (3)0.0141 (2)0.0010 (2)0.0016 (2)0.0025 (2)
C4B0.0154 (3)0.0255 (4)0.0173 (3)0.0018 (3)0.0020 (2)0.0059 (3)
C5B0.0207 (4)0.0448 (7)0.0345 (5)0.0039 (4)0.0048 (4)0.0076 (5)
Geometric parameters (Å, º) top
O1A—C1A1.2550 (9)C6A—H13A0.962 (11)
O2A—C1A1.2666 (9)S1B—C5B1.8035 (12)
N1A—C2A1.4968 (9)S1B—C4B1.8136 (9)
N1A—H1A0.90 (2)O1B—C1B1.2541 (9)
N1A—H2A0.94 (2)O2B—C1B1.2655 (8)
N1A—H3A0.885 (15)N1B—C2B1.4958 (9)
C1A—C2A1.5421 (9)N1B—H1B0.91 (2)
C2A—C3A1.5459 (10)N1B—H2B0.90 (2)
C2A—H4A0.92 (2)N1B—H3B0.89 (2)
C3A—C4A1.5318 (12)C1B—C2B1.5327 (9)
C3A—C5A1.5378 (10)C2B—C3B1.5354 (10)
C3A—H5A1.03 (2)C2B—H4B0.96 (2)
C4A—H6A0.992 (12)C3B—C4B1.5263 (11)
C4A—H7A0.992 (12)C3B—H5B0.959 (11)
C4A—H8A0.992 (12)C3B—H6B0.959 (11)
C5A—C6A1.5317 (13)C4B—H7B0.996 (12)
C5A—H9A1.021 (12)C4B—H8B0.996 (12)
C5A—H10A1.021 (11)C5B—H9B0.941 (12)
C6A—H11A0.962 (11)C5B—H10B0.941 (12)
C6A—H12A0.962 (11)C5B—H11B0.941 (12)
C2A—N1A—H1A110.4 (10)H11A—C6A—H13A109.5
C2A—N1A—H2A111.1 (10)H12A—C6A—H13A109.5
H1A—N1A—H2A108.4 (14)C5B—S1B—C4B100.61 (5)
C2A—N1A—H3A109.0 (9)C2B—N1B—H1B114.1 (10)
H1A—N1A—H3A107.7 (16)C2B—N1B—H2B109.1 (10)
H2A—N1A—H3A110.2 (15)H1B—N1B—H2B106.6 (14)
O1A—C1A—O2A125.82 (7)C2B—N1B—H3B104.5 (10)
O1A—C1A—C2A116.37 (6)H1B—N1B—H3B108.8 (16)
O2A—C1A—C2A117.76 (6)H2B—N1B—H3B113.9 (16)
N1A—C2A—C1A107.60 (5)O1B—C1B—O2B125.95 (7)
N1A—C2A—C3A111.03 (5)O1B—C1B—C2B116.87 (6)
C1A—C2A—C3A110.56 (6)O2B—C1B—C2B117.05 (6)
N1A—C2A—H4A109.21 (4)N1B—C2B—C1B108.93 (6)
C1A—C2A—H4A109.21 (4)N1B—C2B—C3B111.06 (5)
C3A—C2A—H4A109.21 (4)C1B—C2B—C3B108.20 (6)
C4A—C3A—C5A111.03 (7)N1B—C2B—H4B109.54 (4)
C4A—C3A—C2A109.43 (6)C1B—C2B—H4B109.54 (4)
C5A—C3A—C2A112.53 (6)C3B—C2B—H4B109.54 (4)
C4A—C3A—H5A107.89 (6)C4B—C3B—C2B113.95 (6)
C5A—C3A—H5A107.89 (5)C4B—C3B—H5B108.76 (5)
C2A—C3A—H5A107.89 (4)C2B—C3B—H5B108.76 (4)
C3A—C4A—H6A109.47 (5)C4B—C3B—H6B108.76 (5)
C3A—C4A—H7A109.47 (5)C2B—C3B—H6B108.76 (4)
H6A—C4A—H7A109.5H5B—C3B—H6B107.7
C3A—C4A—H8A109.47 (6)C3B—C4B—S1B113.70 (6)
H6A—C4A—H8A109.5C3B—C4B—H7B108.82 (5)
H7A—C4A—H8A109.5S1B—C4B—H7B108.82 (3)
C6A—C5A—C3A113.42 (8)C3B—C4B—H8B108.82 (5)
C6A—C5A—H9A108.89 (6)S1B—C4B—H8B108.82 (3)
C3A—C5A—H9A108.89 (5)H7B—C4B—H8B107.7
C6A—C5A—H10A108.89 (5)S1B—C5B—H9B109.47 (4)
C3A—C5A—H10A108.89 (4)S1B—C5B—H10B109.47 (4)
H9A—C5A—H10A107.7H9B—C5B—H10B109.5
C5A—C6A—H11A109.47 (5)S1B—C5B—H11B109.47 (5)
C5A—C6A—H12A109.47 (6)H9B—C5B—H11B109.5
H11A—C6A—H12A109.5H10B—C5B—H11B109.5
C5A—C6A—H13A109.47 (6)
O1A—C1A—C2A—N1A36.03 (8)C2A—C3A—C5A—C6A179.87 (8)
O2A—C1A—C2A—N1A146.29 (7)O1B—C1B—C2B—N1B32.74 (9)
O1A—C1A—C2A—C3A85.37 (8)O2B—C1B—C2B—N1B151.30 (7)
O2A—C1A—C2A—C3A92.31 (8)O1B—C1B—C2B—C3B88.11 (8)
N1A—C2A—C3A—C4A171.55 (8)O2B—C1B—C2B—C3B87.85 (8)
C1A—C2A—C3A—C4A69.10 (9)N1B—C2B—C3B—C4B54.73 (9)
N1A—C2A—C3A—C5A47.60 (9)C1B—C2B—C3B—C4B174.24 (7)
C1A—C2A—C3A—C5A166.96 (6)C2B—C3B—C4B—S1B178.07 (6)
C4A—C3A—C5A—C6A57.08 (11)C5B—S1B—C4B—C3B79.09 (9)
(B1) L-Isoleucine:D-Valine top
Crystal data top
C6H13NO2·C5H11NO2F(000) = 272
Mr = 248.32Dx = 1.289 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 5.2528 (1) ÅCell parameters from 6101 reflections
b = 23.9809 (6) ŵ = 0.10 mm1
c = 5.4200 (1) ÅT = 150 K
β = 110.420 (1)°Plate, colourless
V = 639.84 (2) Å30.65 × 0.60 × 0.10 mm
Z = 2
Data collection top
Siemens SMART CCD area-detector
diffractometer
6854 independent reflections
Radiation source: fine-focus sealed tube6220 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 40.3°, θmin = 3.4°
Absorption correction: multi-scan
Sheldrick (1996)
h = 99
Tmin = 0.939, Tmax = 0.990k = 4343
10296 measured reflectionsl = 99
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)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111Calculated w = 1/[σ2(Fo2) + (0.039P)2 + 0.1323P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max = 0.001
6854 reflectionsΔρmax = 0.37 e Å3
191 parametersΔρmin = 0.25 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.41 (64)
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
O1A0.8903 (2)0.22269 (4)0.59890 (14)0.01742 (14)
O2A0.4438 (2)0.20401 (4)0.4632 (2)0.01708 (13)
N1A0.9007 (2)0.22898 (4)0.1102 (2)0.01386 (13)
H2A0.888 (4)0.2268 (8)0.071 (4)0.022 (4)*
H3A0.889 (4)0.2642 (8)0.142 (4)0.016 (4)*
H1A1.059 (4)0.2167 (8)0.219 (4)0.019 (4)*
C1A0.6663 (2)0.20966 (4)0.4264 (2)0.01249 (14)
C2A0.6661 (2)0.19912 (4)0.1459 (2)0.01233 (14)
H4A0.489 (3)0.2156 (3)0.014 (2)0.015*
C3A0.6767 (2)0.13645 (4)0.0817 (2)0.01466 (15)
H5A0.7435 (13)0.13369 (6)0.068 (3)0.018*
C4A0.8768 (2)0.10439 (5)0.3132 (2)0.0215 (2)
H6A1.045 (3)0.1252 (4)0.3831 (19)0.032*
H7A0.913 (2)0.0681 (5)0.2531 (10)0.032*
H8A0.7989 (15)0.0996 (5)0.450 (2)0.032*
C5A0.3918 (2)0.11065 (5)0.0075 (3)0.0225 (2)
H9A0.3326 (10)0.10831 (6)0.140 (2)0.027*
H10A0.2685 (19)0.1346 (4)0.136 (2)0.027*
C6A0.3818 (3)0.05255 (6)0.1264 (3)0.0336 (3)
H11A0.199 (3)0.0393 (3)0.188 (3)0.050*
H12A0.493 (3)0.0277 (4)0.005 (2)0.050*
H13A0.447 (3)0.05435 (13)0.270 (3)0.050*
O1B0.3033 (2)0.32034 (4)0.13077 (15)0.01766 (14)
O2B0.7500 (2)0.33844 (3)0.2660 (2)0.01739 (14)
N1B0.2935 (2)0.31423 (4)0.6203 (2)0.01439 (13)
H2B0.291 (4)0.3171 (9)0.783 (4)0.027 (5)*
H1B0.131 (4)0.3273 (9)0.512 (4)0.024 (4)*
H3B0.305 (4)0.2782 (9)0.587 (4)0.028 (5)*
C1B0.5272 (2)0.33311 (4)0.3032 (2)0.01265 (14)
C2B0.5281 (2)0.34390 (4)0.5837 (2)0.01315 (14)
H4B0.686 (3)0.3293 (3)0.702 (2)0.016*
C3B0.5175 (2)0.40683 (4)0.6446 (2)0.0179 (2)
H5B0.4561 (12)0.41015 (8)0.795 (3)0.021*
C4B0.8006 (3)0.43227 (7)0.7244 (3)0.0331 (3)
H6B0.926 (2)0.4112 (5)0.874 (3)0.050*
H7B0.7936 (7)0.4716 (6)0.776 (3)0.050*
H8B0.8658 (17)0.4305 (6)0.574 (3)0.050*
C5B0.3160 (3)0.43878 (5)0.4146 (3)0.0251 (2)
H9B0.145 (3)0.4198 (4)0.356 (2)0.038*
H10B0.3846 (16)0.4409 (5)0.273 (2)0.038*
H11B0.292 (2)0.4756 (6)0.4708 (11)0.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0159 (3)0.0258 (4)0.0107 (3)0.0034 (3)0.0048 (2)0.0027 (2)
O2A0.0142 (3)0.0233 (3)0.0165 (3)0.0008 (3)0.0089 (2)0.0002 (3)
N1A0.0151 (3)0.0174 (3)0.0102 (3)0.0028 (3)0.0059 (2)0.0008 (2)
C1A0.0139 (3)0.0144 (4)0.0106 (3)0.0009 (3)0.0060 (3)0.0002 (3)
C2A0.0129 (3)0.0151 (3)0.0098 (3)0.0001 (3)0.0050 (2)0.0000 (3)
C3A0.0163 (4)0.0150 (4)0.0138 (4)0.0004 (3)0.0066 (3)0.0020 (3)
C4A0.0217 (5)0.0203 (5)0.0216 (5)0.0036 (4)0.0064 (4)0.0015 (4)
C5A0.0188 (4)0.0224 (5)0.0252 (5)0.0047 (4)0.0064 (4)0.0054 (4)
C6A0.0389 (7)0.0207 (5)0.0336 (6)0.0069 (5)0.0033 (5)0.0052 (5)
O1B0.0167 (3)0.0258 (4)0.0113 (3)0.0040 (3)0.0058 (2)0.0027 (2)
O2B0.0160 (3)0.0229 (4)0.0164 (3)0.0011 (3)0.0096 (2)0.0003 (3)
N1B0.0165 (3)0.0171 (3)0.0108 (3)0.0026 (3)0.0064 (3)0.0008 (3)
C1B0.0155 (3)0.0131 (3)0.0108 (3)0.0008 (3)0.0065 (3)0.0004 (3)
C2B0.0137 (3)0.0171 (4)0.0092 (3)0.0011 (3)0.0048 (2)0.0013 (3)
C3B0.0207 (4)0.0181 (4)0.0179 (4)0.0037 (3)0.0106 (3)0.0046 (3)
C4B0.0284 (6)0.0336 (7)0.0393 (7)0.0162 (5)0.0143 (5)0.0161 (6)
C5B0.0315 (6)0.0179 (5)0.0295 (6)0.0041 (4)0.0151 (5)0.0040 (4)
Geometric parameters (Å, º) top
O1A—C1A1.2604 (12)C6A—H13A0.956 (14)
O2A—C1A1.2600 (12)O1B—C1B1.2585 (12)
N1A—C2A1.4947 (12)O2B—C1B1.2614 (12)
N1A—H2A0.96 (2)N1B—C2B1.4944 (13)
N1A—H3A0.87 (2)N1B—H2B0.89 (2)
N1A—H1A0.89 (2)N1B—H1B0.91 (2)
C1A—C2A1.5410 (13)N1B—H3B0.89 (2)
C2A—C3A1.5478 (13)C1B—C2B1.5408 (13)
C2A—H4A1.03 (2)C2B—C3B1.5497 (14)
C3A—C4A1.533 (2)C2B—H4B0.92 (2)
C3A—C5A1.5334 (15)C3B—C4B1.524 (2)
C3A—H5A0.99 (2)C3B—C5B1.530 (2)
C4A—H6A0.970 (13)C3B—H5B0.98 (2)
C4A—H7A0.970 (13)C4B—H6B0.99 (2)
C4A—H8A0.970 (13)C4B—H7B0.99 (2)
C5A—C6A1.528 (2)C4B—H8B0.99 (2)
C5A—H9A0.957 (15)C5B—H9B0.957 (14)
C5A—H10A0.957 (15)C5B—H10B0.957 (14)
C6A—H11A0.956 (14)C5B—H11B0.957 (14)
C6A—H12A0.956 (14)
C2A—N1A—H2A109.8 (11)C5A—C6A—H13A109.47 (8)
C2A—N1A—H3A108.8 (12)H11A—C6A—H13A109.5
H2A—N1A—H3A105.6 (18)H12A—C6A—H13A109.5
C2A—N1A—H1A112.2 (12)C2B—N1B—H2B113.2 (13)
H2A—N1A—H1A112.2 (16)C2B—N1B—H1B112.5 (12)
H3A—N1A—H1A108.0 (18)H2B—N1B—H1B106.1 (17)
O2A—C1A—O1A125.92 (9)C2B—N1B—H3B108.5 (14)
O2A—C1A—C2A117.23 (8)H2B—N1B—H3B108 (2)
O1A—C1A—C2A116.85 (8)H1B—N1B—H3B108.8 (19)
N1A—C2A—C1A109.40 (7)O1B—C1B—O2B125.78 (9)
N1A—C2A—C3A109.89 (7)O1B—C1B—C2B116.99 (8)
C1A—C2A—C3A113.16 (8)O2B—C1B—C2B117.22 (8)
N1A—C2A—H4A108.08 (5)N1B—C2B—C1B109.39 (7)
C1A—C2A—H4A108.08 (5)N1B—C2B—C3B110.06 (8)
C3A—C2A—H4A108.08 (5)C1B—C2B—C3B112.68 (8)
C4A—C3A—C5A111.75 (9)N1B—C2B—H4B108.20 (5)
C4A—C3A—C2A111.79 (8)C1B—C2B—H4B108.20 (5)
C5A—C3A—C2A110.79 (8)C3B—C2B—H4B108.20 (5)
C4A—C3A—H5A107.42 (6)C4B—C3B—C5B111.10 (11)
C5A—C3A—H5A107.42 (6)C4B—C3B—C2B110.27 (10)
C2A—C3A—H5A107.42 (5)C5B—C3B—C2B112.36 (9)
C3A—C4A—H6A109.47 (6)C4B—C3B—H5B107.63 (7)
C3A—C4A—H7A109.47 (6)C5B—C3B—H5B107.64 (6)
H6A—C4A—H7A109.5C2B—C3B—H5B107.64 (5)
C3A—C4A—H8A109.47 (6)C3B—C4B—H6B109.47 (9)
H6A—C4A—H8A109.5C3B—C4B—H7B109.47 (7)
H7A—C4A—H8A109.5H6B—C4B—H7B109.5
C6A—C5A—C3A112.79 (11)C3B—C4B—H8B109.47 (7)
C6A—C5A—H9A109.03 (8)H6B—C4B—H8B109.5
C3A—C5A—H9A109.03 (6)H7B—C4B—H8B109.5
C6A—C5A—H10A109.03 (8)C3B—C5B—H9B109.47 (6)
C3A—C5A—H10A109.03 (6)C3B—C5B—H10B109.47 (6)
H9A—C5A—H10A107.8H9B—C5B—H10B109.5
C5A—C6A—H11A109.47 (8)C3B—C5B—H11B109.47 (6)
C5A—C6A—H12A109.47 (8)H9B—C5B—H11B109.5
H11A—C6A—H12A109.5H10B—C5B—H11B109.5
O2A—C1A—C2A—N1A157.01 (9)C2A—C3A—C5A—C6A168.22 (10)
O1A—C1A—C2A—N1A23.60 (12)O1B—C1B—C2B—N1B23.92 (12)
O2A—C1A—C2A—C3A80.10 (11)O2B—C1B—C2B—N1B156.83 (8)
O1A—C1A—C2A—C3A99.28 (10)O1B—C1B—C2B—C3B98.84 (10)
N1A—C2A—C3A—C4A80.72 (10)O2B—C1B—C2B—C3B80.40 (11)
C1A—C2A—C3A—C4A41.89 (11)N1B—C2B—C3B—C4B155.56 (10)
N1A—C2A—C3A—C5A153.91 (9)C1B—C2B—C3B—C4B82.05 (12)
C1A—C2A—C3A—C5A83.47 (10)N1B—C2B—C3B—C5B79.91 (10)
C4A—C3A—C5A—C6A66.40 (13)C1B—C2B—C3B—C5B42.47 (12)
(B2) L-Isoleucine:D-Leucine top
Crystal data top
C6H13NO2·C6H13NO2V = 355.16 (3) Å3
Mr = 262.35Z = 1
Triclinic, P1F(000) = 144
Hall symbol: P 1Dx = 1.227 Mg m3
a = 5.1933 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 5.4064 (3) ÅCell parameters from 1220 reflections
c = 13.6968 (7) ŵ = 0.09 mm1
α = 91.516 (2)°T = 150 K
β = 98.603 (2)°Block, colourless
γ = 110.376 (2)°0.20 × 0.10 × 0.10 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
4689 independent reflections
Radiation source: fine-focus sealed tube4082 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 40.6°, θmin = 3.0°
Absorption correction: multi-scan
Sheldrick (1996)
h = 79
Tmin = 0.982, Tmax = 0.990k = 98
5657 measured reflectionsl = 2324
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)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134Calculated w = 1/[σ2(Fo2) + (0.0348P)2 + 0.086P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.006
4689 reflectionsΔρmax = 0.59 e Å3
201 parametersΔρmin = 0.40 e Å3
3 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 1.00 (100)
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
O1A1.0178 (3)0.6454 (2)0.54362 (10)0.0165 (2)
O2A0.5853 (2)0.5199 (2)0.57867 (10)0.0153 (2)
N1A1.0229 (3)0.1534 (3)0.53328 (11)0.0123 (2)
H1A1.202 (6)0.270 (5)0.557 (2)0.014 (6)*
H2A1.029 (7)0.020 (7)0.541 (3)0.030 (8)*
H3A0.989 (9)0.179 (8)0.464 (3)0.041 (9)*
C1A0.8048 (3)0.4791 (3)0.56787 (12)0.0118 (2)
C2A0.8136 (3)0.2029 (3)0.58754 (11)0.0113 (2)
H4A0.630 (5)0.071 (4)0.5611 (7)0.014*
C3A0.8831 (3)0.1687 (3)0.69866 (12)0.0136 (3)
H5A0.960 (2)0.011 (4)0.7044 (2)0.016*
C4A1.1104 (3)0.4169 (3)0.75451 (12)0.0189 (3)
H6A1.0352 (18)0.554 (3)0.7608 (12)0.028*
H7A1.263 (3)0.476 (2)0.7185 (10)0.028*
H8A1.176 (3)0.3760 (13)0.8191 (13)0.028*
C5A0.6183 (4)0.0893 (4)0.74578 (14)0.0215 (3)
H9A0.5548 (16)0.238 (4)0.74755 (14)0.026*
H10A0.473 (3)0.056 (3)0.7045 (10)0.026*
C6A0.6617 (5)0.0056 (5)0.8503 (2)0.0344 (5)
H11A0.726 (5)0.136 (5)0.8494 (3)0.052*
H12A0.492 (5)0.047 (5)0.8743 (10)0.052*
H13A0.794 (5)0.149 (4)0.8918 (11)0.052*
O1B0.3447 (3)0.1377 (2)0.37011 (10)0.0166 (2)
O2B0.7841 (2)0.2726 (2)0.34070 (10)0.0157 (2)
N1B0.3519 (3)0.6373 (3)0.38544 (11)0.0135 (2)
H1B0.164 (6)0.524 (6)0.365 (2)0.018 (6)*
H2B0.363 (6)0.788 (6)0.378 (2)0.019 (7)*
H3B0.419 (6)0.621 (6)0.450 (2)0.017 (6)*
C1B0.5594 (3)0.3070 (3)0.34688 (11)0.0113 (2)
C2B0.5377 (3)0.5762 (3)0.32302 (11)0.0110 (2)
H4B0.709 (5)0.704 (4)0.3362 (4)0.013*
C3B0.4115 (4)0.5682 (3)0.21343 (13)0.0164 (3)
H5B0.242 (4)0.413 (3)0.1980 (3)0.020*
H6B0.3601 (11)0.724 (3)0.2043 (2)0.020*
C4B0.6025 (4)0.5595 (3)0.13970 (13)0.0198 (3)
H7B0.699 (3)0.430 (4)0.1612 (7)0.024*
C5B0.4294 (6)0.4604 (5)0.0367 (2)0.0367 (5)
H8B0.338 (5)0.578 (4)0.0158 (10)0.055*
H9B0.296 (5)0.290 (5)0.0389 (4)0.055*
H10B0.548 (3)0.452 (5)0.0085 (13)0.055*
C6B0.8267 (5)0.8318 (4)0.1368 (2)0.0285 (4)
H11B0.955 (4)0.8161 (9)0.0950 (17)0.043*
H12B0.926 (4)0.898 (3)0.2031 (15)0.043*
H13B0.740 (2)0.953 (3)0.1106 (16)0.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0171 (5)0.0101 (4)0.0253 (6)0.0065 (4)0.0076 (4)0.0054 (4)
O2A0.0145 (5)0.0147 (5)0.0194 (5)0.0085 (4)0.0030 (4)0.0025 (4)
N1A0.0149 (5)0.0092 (5)0.0156 (6)0.0065 (4)0.0051 (4)0.0038 (4)
C1A0.0136 (6)0.0087 (5)0.0140 (6)0.0055 (4)0.0016 (4)0.0025 (4)
C2A0.0126 (6)0.0091 (5)0.0134 (6)0.0048 (4)0.0026 (4)0.0027 (4)
C3A0.0167 (6)0.0107 (5)0.0149 (6)0.0066 (4)0.0025 (5)0.0035 (4)
C4A0.0191 (7)0.0194 (7)0.0153 (6)0.0046 (5)0.0000 (5)0.0010 (5)
C5A0.0197 (7)0.0230 (7)0.0226 (8)0.0060 (6)0.0090 (6)0.0078 (6)
C6A0.0406 (12)0.0379 (11)0.0188 (8)0.0037 (9)0.0119 (8)0.0088 (7)
O1B0.0176 (5)0.0103 (5)0.0249 (6)0.0065 (4)0.0078 (4)0.0067 (4)
O2B0.0146 (5)0.0152 (5)0.0204 (6)0.0090 (4)0.0030 (4)0.0035 (4)
N1B0.0159 (6)0.0092 (5)0.0176 (6)0.0066 (4)0.0042 (4)0.0038 (4)
C1B0.0134 (6)0.0098 (5)0.0116 (6)0.0057 (4)0.0010 (4)0.0017 (4)
C2B0.0118 (5)0.0092 (5)0.0136 (6)0.0054 (4)0.0031 (4)0.0028 (4)
C3B0.0180 (7)0.0175 (6)0.0152 (6)0.0080 (5)0.0024 (5)0.0058 (5)
C4B0.0282 (8)0.0207 (7)0.0140 (6)0.0116 (6)0.0068 (5)0.0044 (5)
C5B0.0500 (14)0.0376 (11)0.0154 (8)0.0082 (10)0.0030 (8)0.0020 (7)
C6B0.0269 (8)0.0311 (9)0.0266 (9)0.0065 (7)0.0101 (7)0.0107 (7)
Geometric parameters (Å, º) top
O1A—C1A1.255 (2)O1B—C1B1.262 (2)
O2A—C1A1.262 (2)O2B—C1B1.258 (2)
N1A—C2A1.496 (2)N1B—C2B1.492 (2)
N1A—H1A0.93 (3)N1B—H1B0.95 (3)
N1A—H2A0.96 (4)N1B—H2B0.81 (3)
N1A—H3A0.97 (4)N1B—H3B0.92 (3)
C1A—C2A1.539 (2)C1B—C2B1.538 (2)
C2A—C3A1.542 (2)C2B—C3B1.538 (2)
C2A—H4A0.98 (3)C2B—H4B0.91 (3)
C3A—C4A1.534 (2)C3B—C4B1.528 (3)
C3A—C5A1.536 (2)C3B—H5B0.97 (2)
C3A—H5A1.06 (3)C3B—H6B0.97 (2)
C4A—H6A0.96 (2)C4B—C5B1.527 (3)
C4A—H7A0.96 (2)C4B—C6B1.532 (3)
C4A—H8A0.96 (2)C4B—H7B1.02 (3)
C5A—C6A1.521 (3)C5B—H8B0.95 (2)
C5A—H9A0.97 (2)C5B—H9B0.95 (2)
C5A—H10A0.97 (2)C5B—H10B0.95 (2)
C6A—H11A0.94 (2)C6B—H11B0.97 (2)
C6A—H12A0.94 (2)C6B—H12B0.97 (2)
C6A—H13A0.94 (2)C6B—H13B0.97 (2)
C2A—N1A—H1A111.5 (18)C2B—N1B—H1B110.9 (19)
C2A—N1A—H2A112 (2)C2B—N1B—H2B107 (2)
H1A—N1A—H2A106 (3)H1B—N1B—H2B109 (3)
C2A—N1A—H3A112 (3)C2B—N1B—H3B106.9 (19)
H1A—N1A—H3A106 (3)H1B—N1B—H3B113 (3)
H2A—N1A—H3A110 (3)H2B—N1B—H3B110 (3)
O1A—C1A—O2A125.61 (15)O2B—C1B—O1B125.76 (15)
O1A—C1A—C2A117.17 (14)O2B—C1B—C2B118.25 (13)
O2A—C1A—C2A117.22 (13)O1B—C1B—C2B115.98 (14)
N1A—C2A—C1A109.06 (12)N1B—C2B—C1B109.08 (12)
N1A—C2A—C3A109.94 (13)N1B—C2B—C3B108.37 (13)
C1A—C2A—C3A113.05 (13)C1B—C2B—C3B110.58 (13)
N1A—C2A—H4A108.22 (8)N1B—C2B—H4B109.60 (8)
C1A—C2A—H4A108.22 (8)C1B—C2B—H4B109.60 (8)
C3A—C2A—H4A108.22 (8)C3B—C2B—H4B109.60 (8)
C4A—C3A—C5A111.35 (14)C4B—C3B—C2B114.99 (14)
C4A—C3A—C2A112.08 (12)C4B—C3B—H5B108.52 (9)
C5A—C3A—C2A110.50 (14)C2B—C3B—H5B108.52 (8)
C4A—C3A—H5A107.56 (9)C4B—C3B—H6B108.52 (9)
C5A—C3A—H5A107.56 (9)C2B—C3B—H6B108.52 (9)
C2A—C3A—H5A107.56 (9)H5B—C3B—H6B107.5
C3A—C4A—H6A109.47 (10)C5B—C4B—C3B109.7 (2)
C3A—C4A—H7A109.47 (9)C5B—C4B—C6B110.2 (2)
H6A—C4A—H7A109.5C3B—C4B—C6B111.5 (2)
C3A—C4A—H8A109.47 (8)C5B—C4B—H7B108.46 (13)
H6A—C4A—H8A109.5C3B—C4B—H7B108.46 (9)
H7A—C4A—H8A109.5C6B—C4B—H7B108.46 (11)
C6A—C5A—C3A113.2 (2)C4B—C5B—H8B109.47 (13)
C6A—C5A—H9A108.93 (14)C4B—C5B—H9B109.47 (11)
C3A—C5A—H9A108.93 (9)H8B—C5B—H9B109.5
C6A—C5A—H10A108.93 (12)C4B—C5B—H10B109.47 (13)
C3A—C5A—H10A108.93 (9)H8B—C5B—H10B109.5
H9A—C5A—H10A107.7H9B—C5B—H10B109.5
C5A—C6A—H11A109.47 (14)C4B—C6B—H11B109.47 (11)
C5A—C6A—H12A109.47 (12)C4B—C6B—H12B109.47 (10)
H11A—C6A—H12A109.5H11B—C6B—H12B109.5
C5A—C6A—H13A109.47 (12)C4B—C6B—H13B109.47 (11)
H11A—C6A—H13A109.5H11B—C6B—H13B109.5
H12A—C6A—H13A109.5H12B—C6B—H13B109.5
O1A—C1A—C2A—N1A23.9 (2)C2A—C3A—C5A—C6A169.9 (2)
O2A—C1A—C2A—N1A156.94 (14)O2B—C1B—C2B—N1B147.82 (14)
O1A—C1A—C2A—C3A98.7 (2)O1B—C1B—C2B—N1B33.0 (2)
O2A—C1A—C2A—C3A80.4 (2)O2B—C1B—C2B—C3B93.1 (2)
N1A—C2A—C3A—C4A81.6 (2)O1B—C1B—C2B—C3B86.1 (2)
C1A—C2A—C3A—C4A40.5 (2)N1B—C2B—C3B—C4B169.01 (13)
N1A—C2A—C3A—C5A153.54 (13)C1B—C2B—C3B—C4B71.5 (2)
C1A—C2A—C3A—C5A84.3 (2)C2B—C3B—C4B—C5B161.1 (2)
C4A—C3A—C5A—C6A64.8 (2)C2B—C3B—C4B—C6B76.5 (2)
 
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