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
| Portable Document Format (PDF) file Supplementary material |
| Crystallographic Information File (CIF) Contains datablocks L1, L2, L3, L4, L5, B1, B2, global |
| Structure factor file (CIF format) Contains datablock l-ile:d-val |
| Structure factor file (CIF format) Contains datablock l-ile:d-leu |
| Structure factor file (CIF format) Contains datablock l-ile:d-ala |
| Structure factor file (CIF format) Contains datablock l-ile:d-n-abut |
| Structure factor file (CIF format) Contains datablock l-ile:d-nval |
| Structure factor file (CIF format) Contains datablock l-ile:d-nleu |
| Structure factor file (CIF format) Contains datablock l-ile:d-met |
| Structure factor file (CIF format) Contains datablock B1 |
| Structure factor file (CIF format) Contains datablock B2 |
| Structure factor file (CIF format) Contains datablock L1 |
| Structure factor file (CIF format) Supplementary material |
| Structure factor file (CIF format) Supplementary material |
| Structure factor file (CIF format) Supplementary material |
| Structure factor file (CIF format) Supplementary material |
CCDC references: 131793; 131794; 131795; 131796; 131797; 131798; 131799
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·C3H7NO2 | F(000) = 240 |
Mr = 220.27 | Dx = 1.210 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8944 (2) Å | Cell parameters from 6890 reflections |
b = 4.7425 (1) Å | µ = 0.09 mm−1 |
c = 12.9045 (2) Å | T = 150 K |
β = 93.374 (1)° | Plate, colourless |
V = 604.48 (2) Å3 | 1.05 × 0.25 × 0.05 mm |
Z = 2 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 8985 independent reflections |
Radiation source: fine-focus sealed tube | 6393 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
ω scans | θmax = 49.9°, θmin = 2.1° |
Absorption correction: multi-scan Sheldrick (1996) | h = −21→21 |
Tmin = 0.906, Tmax = 0.995 | k = −9→9 |
15033 measured reflections | l = −20→26 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.061 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.170 | Calculated w = 1/[σ2(Fo2) + (0.087P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.002 |
8985 reflections | Δρmax = 0.60 e Å−3 |
164 parameters | Δρmin = −0.47 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
O1A | 0.54349 (7) | 0.4792 (2) | 0.41500 (5) | 0.01780 (12) | |
N1A | 0.34977 (7) | 0.0829 (2) | 0.38307 (5) | 0.01534 (12) | |
H1A | 0.3046 (15) | 0.257 (4) | 0.3749 (13) | 0.023* | |
H2A | 0.2927 (16) | −0.040 (4) | 0.3755 (14) | 0.023* | |
H3A | 0.3887 (15) | 0.058 (5) | 0.4450 (12) | 0.023* | |
O2A | 0.69873 (6) | 0.1971 (2) | 0.34906 (6) | 0.02267 (14) | |
C1A | 0.57861 (8) | 0.2684 (2) | 0.36447 (6) | 0.01448 (14) | |
C2A | 0.46474 (8) | 0.0873 (2) | 0.31255 (6) | 0.01345 (12) | |
H4A | 0.4994 (6) | −0.114 (3) | 0.3029 (2) | 0.016* | |
C3A | 0.41773 (9) | 0.2111 (2) | 0.20576 (6) | 0.01788 (14) | |
H5A | 0.3832 (6) | 0.405 (3) | 0.2180 (2) | 0.021* | |
C4A | 0.53563 (14) | 0.2384 (5) | 0.13543 (10) | 0.0478 (5) | |
H6A | 0.6055 (12) | 0.355 (3) | 0.1690 (7) | 0.072* | |
H7A | 0.5042 (6) | 0.324 (3) | 0.0704 (10) | 0.072* | |
H8A | 0.5720 (11) | 0.053 (3) | 0.1223 (10) | 0.072* | |
C5A | 0.3010 (2) | 0.0419 (4) | 0.15395 (10) | 0.0433 (4) | |
H9A | 0.3342 (6) | −0.136 (3) | 0.1349 (3) | 0.052* | |
H10 | 0.2357 (11) | 0.0113 (7) | 0.2029 (9) | 0.052* | |
C6A | 0.23222 (14) | 0.1796 (4) | 0.05839 (9) | 0.0401 (3) | |
H11 | 0.1508 (13) | 0.069 (2) | 0.0352 (8) | 0.060* | |
H12 | 0.2961 (10) | 0.185 (3) | 0.0019 (8) | 0.060* | |
H13 | 0.2048 (14) | 0.375 (3) | 0.0757 (4) | 0.060* | |
O1B | 1.04247 (7) | 0.3207 (2) | 0.41788 (5) | 0.01882 (13) | |
N1B | 0.84594 (8) | 0.7006 (2) | 0.38644 (6) | 0.01696 (13) | |
H1B | 0.8049 (16) | 0.538 (5) | 0.3858 (13) | 0.025* | |
H2B | 0.7833 (16) | 0.843 (4) | 0.3679 (13) | 0.025* | |
H3B | 0.8731 (15) | 0.718 (4) | 0.4538 (12) | 0.025* | |
O2B | 1.19725 (7) | 0.5869 (2) | 0.34404 (6) | 0.02225 (14) | |
C1B | 1.07737 (8) | 0.5285 (2) | 0.36618 (6) | 0.01445 (13) | |
C2B | 0.96581 (8) | 0.7264 (2) | 0.32264 (7) | 0.01610 (14) | |
H4B | 0.9970 (6) | 0.908 (4) | 0.32651 (10) | 0.019* | |
C3B | 0.92580 (12) | 0.6565 (3) | 0.20954 (8) | 0.0302 (3) | |
H5B | 0.8594 (14) | 0.794 (2) | 0.1820 (4) | 0.045* | |
H6B | 0.8863 (13) | 0.468 (3) | 0.2053 (2) | 0.045* | |
H7B | 1.0061 (10) | 0.663 (3) | 0.1689 (6) | 0.045* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0174 (3) | 0.0160 (3) | 0.0195 (2) | −0.0005 (2) | −0.0027 (2) | −0.0030 (2) |
N1A | 0.0116 (3) | 0.0173 (3) | 0.0168 (2) | −0.0020 (2) | −0.0014 (2) | 0.0023 (2) |
O2A | 0.0109 (2) | 0.0187 (3) | 0.0382 (4) | 0.0004 (2) | −0.0002 (2) | −0.0004 (3) |
C1A | 0.0118 (3) | 0.0129 (3) | 0.0184 (3) | −0.0011 (2) | −0.0022 (2) | 0.0015 (2) |
C2A | 0.0113 (3) | 0.0126 (3) | 0.0163 (3) | −0.0001 (2) | −0.0006 (2) | 0.0003 (2) |
C3A | 0.0177 (3) | 0.0195 (4) | 0.0162 (3) | −0.0021 (3) | −0.0012 (2) | 0.0015 (3) |
C4A | 0.0303 (6) | 0.0918 (14) | 0.0220 (4) | 0.0037 (8) | 0.0083 (4) | 0.0122 (7) |
C5A | 0.0533 (8) | 0.0441 (7) | 0.0292 (5) | −0.0276 (6) | −0.0240 (5) | 0.0141 (5) |
C6A | 0.0371 (6) | 0.0577 (9) | 0.0237 (4) | −0.0052 (6) | −0.0132 (4) | 0.0061 (5) |
O1B | 0.0171 (3) | 0.0153 (3) | 0.0238 (3) | 0.0002 (2) | −0.0009 (2) | 0.0036 (2) |
N1B | 0.0116 (3) | 0.0165 (3) | 0.0226 (3) | 0.0014 (2) | −0.0009 (2) | −0.0019 (3) |
O2B | 0.0114 (2) | 0.0198 (3) | 0.0357 (3) | −0.0004 (2) | 0.0028 (2) | 0.0016 (3) |
C1B | 0.0114 (3) | 0.0132 (3) | 0.0184 (3) | 0.0002 (2) | −0.0019 (2) | −0.0017 (2) |
C2B | 0.0128 (3) | 0.0154 (3) | 0.0199 (3) | 0.0004 (3) | −0.0011 (2) | 0.0021 (3) |
C3B | 0.0261 (5) | 0.0457 (7) | 0.0183 (3) | 0.0038 (5) | −0.0030 (3) | 0.0018 (4) |
Geometric parameters (Å, º) top
O1A—C1A | 1.2540 (11) | C5A—H10 | 0.94 (2) |
N1A—C2A | 1.4981 (11) | C6A—H11 | 0.993 (13) |
N1A—H1A | 0.94 (2) | C6A—H12 | 0.993 (13) |
N1A—H2A | 0.81 (2) | C6A—H13 | 0.993 (13) |
N1A—H3A | 0.87 (2) | O1B—C1B | 1.2499 (11) |
O2A—C1A | 1.2626 (11) | N1B—C2B | 1.4882 (12) |
C1A—C2A | 1.5383 (11) | N1B—H1B | 0.87 (2) |
C2A—C3A | 1.5443 (11) | N1B—H2B | 0.94 (2) |
C2A—H4A | 1.03 (2) | N1B—H3B | 0.90 (2) |
C3A—C4A | 1.5251 (15) | O2B—C1B | 1.2669 (11) |
C3A—C5A | 1.5275 (14) | C1B—C2B | 1.5305 (12) |
C3A—H5A | 1.00 (2) | C2B—C3B | 1.5261 (13) |
C4A—H6A | 0.967 (13) | C2B—H4B | 0.92 (2) |
C4A—H7A | 0.967 (13) | C3B—H5B | 0.978 (11) |
C4A—H8A | 0.967 (13) | C3B—H6B | 0.978 (11) |
C5A—C6A | 1.520 (2) | C3B—H7B | 0.978 (11) |
C5A—H9A | 0.94 (2) | | |
| | | |
C2A—N1A—H1A | 107.0 (10) | C6A—C5A—H10 | 108.55 (8) |
C2A—N1A—H2A | 118.9 (12) | C3A—C5A—H10 | 108.55 (7) |
H1A—N1A—H2A | 107.0 (15) | H9A—C5A—H10 | 107.5 |
C2A—N1A—H3A | 104.3 (10) | C5A—C6A—H11 | 109.47 (8) |
H1A—N1A—H3A | 113.6 (17) | C5A—C6A—H12 | 109.47 (9) |
H2A—N1A—H3A | 106.3 (18) | H11—C6A—H12 | 109.5 |
O1A—C1A—O2A | 126.00 (8) | C5A—C6A—H13 | 109.47 (10) |
O1A—C1A—C2A | 116.94 (7) | H11—C6A—H13 | 109.5 |
O2A—C1A—C2A | 117.00 (8) | H12—C6A—H13 | 109.5 |
N1A—C2A—C1A | 107.83 (7) | C2B—N1B—H1B | 117.0 (12) |
N1A—C2A—C3A | 110.35 (6) | C2B—N1B—H2B | 109.6 (11) |
C1A—C2A—C3A | 110.54 (7) | H1B—N1B—H2B | 109.5 (14) |
N1A—C2A—H4A | 109.36 (5) | C2B—N1B—H3B | 109.0 (10) |
C1A—C2A—H4A | 109.36 (5) | H1B—N1B—H3B | 101.8 (16) |
C3A—C2A—H4A | 109.36 (5) | H2B—N1B—H3B | 109.7 (16) |
C4A—C3A—C5A | 111.65 (11) | O1B—C1B—O2B | 125.76 (8) |
C4A—C3A—C2A | 111.25 (8) | O1B—C1B—C2B | 117.62 (7) |
C5A—C3A—C2A | 111.78 (8) | O2B—C1B—C2B | 116.59 (8) |
C4A—C3A—H5A | 107.29 (10) | N1B—C2B—C3B | 109.93 (7) |
C5A—C3A—H5A | 107.29 (8) | N1B—C2B—C1B | 109.11 (7) |
C2A—C3A—H5A | 107.29 (5) | C3B—C2B—C1B | 111.02 (8) |
C3A—C4A—H6A | 109.47 (8) | N1B—C2B—H4B | 108.92 (5) |
C3A—C4A—H7A | 109.47 (6) | C3B—C2B—H4B | 108.92 (7) |
H6A—C4A—H7A | 109.5 | C1B—C2B—H4B | 108.92 (5) |
C3A—C4A—H8A | 109.47 (10) | C2B—C3B—H5B | 109.47 (6) |
H6A—C4A—H8A | 109.5 | C2B—C3B—H6B | 109.47 (7) |
H7A—C4A—H8A | 109.5 | H5B—C3B—H6B | 109.5 |
C6A—C5A—C3A | 114.85 (11) | C2B—C3B—H7B | 109.47 (6) |
C6A—C5A—H9A | 108.55 (10) | H5B—C3B—H7B | 109.5 |
C3A—C5A—H9A | 108.55 (8) | H6B—C3B—H7B | 109.5 |
| | | |
O1A—C1A—C2A—N1A | −35.95 (10) | C1A—C2A—C3A—C5A | −177.92 (10) |
O2A—C1A—C2A—N1A | 146.62 (8) | C4A—C3A—C5A—C6A | −65.3 (2) |
O1A—C1A—C2A—C3A | 84.76 (9) | C2A—C3A—C5A—C6A | 169.34 (12) |
O2A—C1A—C2A—C3A | −92.67 (10) | O1B—C1B—C2B—N1B | 23.75 (11) |
N1A—C2A—C3A—C4A | 175.71 (12) | O2B—C1B—C2B—N1B | −158.01 (8) |
C1A—C2A—C3A—C4A | 56.51 (13) | O1B—C1B—C2B—C3B | −97.55 (10) |
N1A—C2A—C3A—C5A | −58.72 (12) | O2B—C1B—C2B—C3B | 80.69 (11) |
(L2)
L-Isoleucine:
D-aminobutyric acid
top
Crystal data top
C6H13NO2·C4H9NO2 | F(000) = 512 |
Mr = 234.30 | Dx = 1.223 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
a = 26.9873 (6) Å | Cell parameters from 8192 reflections |
b = 4.7471 (1) Å | µ = 0.09 mm−1 |
c = 9.9652 (2) Å | T = 170 K |
β = 94.546 (1)° | Plate, colourless |
V = 1272.64 (5) Å3 | 0.90 × 0.40 × 0.10 mm |
Z = 4 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 6238 independent reflections |
Radiation source: fine-focus sealed tube | 5817 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω scans | θmax = 39.1°, θmin = 2.1° |
Absorption correction: multi-scan Sheldrick (1996) | h = −47→46 |
Tmin = 0.919, Tmax = 0.991 | k = −8→8 |
10909 measured reflections | l = −17→16 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.039 | Calculated w = 1/[σ2(Fo2) + (0.0467P)2 + 0.3251P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.104 | (Δ/σ)max = 0.002 |
S = 1.09 | Δρmax = 0.38 e Å−3 |
6238 reflections | Δρmin = −0.25 e Å−3 |
177 parameters | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0139 (18) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute 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 | x | y | z | Uiso*/Ueq | |
O1A | 0.20762 (2) | −0.18301 (14) | 0.54181 (6) | 0.01934 (11) | |
O2A | 0.17540 (3) | 0.1093 (2) | 0.68909 (6) | 0.02388 (12) | |
N1A | 0.19630 (2) | 0.2099 (2) | 0.34594 (6) | 0.01639 (11) | |
H1A | 0.1951 (5) | 0.059 (4) | 0.3046 (13) | 0.019 (3)* | |
H2A | 0.1898 (6) | 0.358 (4) | 0.2824 (15) | 0.034 (4)* | |
H3A | 0.2270 (5) | 0.247 (4) | 0.3859 (15) | 0.029 (4)* | |
C1A | 0.18363 (3) | 0.0317 (2) | 0.57158 (7) | 0.01544 (12) | |
C2A | 0.16044 (3) | 0.2075 (2) | 0.45311 (7) | 0.01488 (11) | |
H4A | 0.15508 (9) | 0.400 (3) | 0.4833 (5) | 0.018* | |
C3A | 0.11034 (3) | 0.0791 (2) | 0.39756 (8) | 0.01897 (13) | |
H5A | 0.11622 (10) | −0.109 (3) | 0.3763 (4) | 0.023* | |
C4A | 0.07301 (3) | 0.0813 (4) | 0.50479 (11) | 0.0500 (4) | |
H11A | 0.08726 (5) | −0.0108 (7) | 0.5846 (2) | 0.075* | |
H12A | 0.04338 (6) | −0.0164 (3) | 0.47158 (14) | 0.075* | |
H13A | 0.06489 (5) | 0.2724 (3) | 0.5257 (2) | 0.075* | |
C5A | 0.08951 (3) | 0.2255 (3) | 0.26779 (11) | 0.0329 (2) | |
H6A | 0.08468 (4) | 0.4241 (3) | 0.28667 (12) | 0.039* | |
H7A | 0.11391 (4) | 0.2122 (3) | 0.20133 (14) | 0.039* | |
C6A | 0.04046 (4) | 0.1025 (3) | 0.20776 (12) | 0.0392 (3) | |
H8A | 0.0317 (3) | 0.188 (2) | 0.1207 (12) | 0.059* | |
H9A | 0.0146 (3) | 0.141 (2) | 0.2674 (9) | 0.059* | |
H10A | 0.04393 (15) | −0.099 (2) | 0.1970 (12) | 0.059* | |
O1B | 0.21244 (2) | 0.98963 (14) | 1.04018 (6) | 0.02036 (11) | |
O2B | 0.18223 (3) | 0.7066 (2) | 1.19395 (6) | 0.02475 (13) | |
N1B | 0.19418 (3) | 0.6073 (2) | 0.84225 (6) | 0.01767 (11) | |
H1B | 0.1907 (5) | 0.792 (4) | 0.7976 (14) | 0.025 (3)* | |
H2B | 0.1844 (5) | 0.473 (4) | 0.7834 (14) | 0.026 (4)* | |
H3B | 0.2261 (5) | 0.578 (4) | 0.8696 (14) | 0.027 (3)* | |
C1B | 0.18923 (3) | 0.7767 (2) | 1.07458 (7) | 0.01622 (12) | |
C2B | 0.16422 (3) | 0.5946 (2) | 0.96181 (7) | 0.01621 (12) | |
H4B | 0.16252 (4) | 0.409 (3) | 0.9913 (5) | 0.019* | |
C3B | 0.11148 (3) | 0.7073 (2) | 0.92737 (10) | 0.0252 (2) | |
H5B | 0.0941 (2) | 0.7101 (2) | 1.0088 (10) | 0.030* | |
H6B | 0.11376 (4) | 0.900 (2) | 0.8963 (4) | 0.030* | |
C4B | 0.08096 (4) | 0.5386 (3) | 0.82100 (15) | 0.0420 (3) | |
H7B | 0.0469 (4) | 0.6303 (19) | 0.8023 (10) | 0.063* | |
H8B | 0.0766 (4) | 0.338 (2) | 0.8547 (6) | 0.063* | |
H9B | 0.0988 (3) | 0.534 (2) | 0.7345 (11) | 0.063* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0217 (2) | 0.0172 (3) | 0.0188 (2) | 0.0032 (2) | −0.0007 (2) | 0.0009 (2) |
O2A | 0.0382 (3) | 0.0206 (3) | 0.0129 (2) | −0.0001 (2) | 0.0029 (2) | −0.0008 (2) |
N1A | 0.0187 (2) | 0.0168 (3) | 0.0137 (2) | −0.0027 (2) | 0.0012 (2) | 0.0015 (2) |
C1A | 0.0187 (3) | 0.0145 (3) | 0.0129 (2) | −0.0019 (2) | 0.0001 (2) | 0.0003 (2) |
C2A | 0.0178 (3) | 0.0134 (3) | 0.0133 (2) | 0.0003 (2) | 0.0008 (2) | 0.0000 (2) |
C3A | 0.0163 (3) | 0.0213 (3) | 0.0191 (3) | −0.0009 (2) | 0.0002 (2) | −0.0007 (3) |
C4A | 0.0220 (4) | 0.0990 (12) | 0.0300 (4) | −0.0107 (6) | 0.0080 (3) | −0.0084 (7) |
C5A | 0.0292 (4) | 0.0327 (5) | 0.0343 (4) | −0.0032 (4) | −0.0132 (3) | 0.0081 (4) |
C6A | 0.0240 (4) | 0.0543 (7) | 0.0370 (5) | 0.0016 (4) | −0.0112 (3) | −0.0046 (5) |
O1B | 0.0251 (3) | 0.0170 (3) | 0.0188 (2) | −0.0040 (2) | 0.0008 (2) | −0.0003 (2) |
O2B | 0.0423 (3) | 0.0194 (3) | 0.0129 (2) | −0.0017 (3) | 0.0049 (2) | 0.0008 (2) |
N1B | 0.0219 (3) | 0.0181 (3) | 0.0130 (2) | 0.0013 (2) | 0.0013 (2) | −0.0017 (2) |
C1B | 0.0208 (3) | 0.0144 (3) | 0.0135 (2) | 0.0020 (2) | 0.0009 (2) | −0.0004 (2) |
C2B | 0.0196 (3) | 0.0142 (3) | 0.0149 (2) | −0.0006 (2) | 0.0018 (2) | 0.0002 (2) |
C3B | 0.0201 (3) | 0.0258 (4) | 0.0295 (4) | 0.0024 (3) | 0.0003 (3) | −0.0039 (3) |
C4B | 0.0280 (4) | 0.0378 (6) | 0.0571 (7) | 0.0024 (4) | −0.0157 (4) | −0.0124 (6) |
Geometric parameters (Å, º) top
O1A—C1A | 1.2558 (10) | C6A—H8A | 0.970 (11) |
O2A—C1A | 1.2640 (9) | C6A—H9A | 0.970 (11) |
N1A—C2A | 1.4971 (9) | C6A—H10A | 0.970 (11) |
N1A—H1A | 0.83 (2) | O1B—C1B | 1.2512 (10) |
N1A—H2A | 0.95 (2) | O2B—C1B | 1.2637 (9) |
N1A—H3A | 0.908 (15) | N1B—C2B | 1.4931 (9) |
C1A—C2A | 1.5376 (10) | N1B—H1B | 0.98 (2) |
C2A—C3A | 1.5451 (10) | N1B—H2B | 0.89 (2) |
C2A—H4A | 0.98 (2) | N1B—H3B | 0.895 (14) |
C3A—C4A | 1.5257 (12) | C1B—C2B | 1.5315 (11) |
C3A—C5A | 1.5350 (12) | C2B—C3B | 1.5336 (11) |
C3A—H5A | 0.94 (2) | C2B—H4B | 0.93 (2) |
C4A—H11A | 0.96 | C3B—C4B | 1.5184 (15) |
C4A—H12A | 0.96 | C3B—H5B | 0.969 (11) |
C4A—H13A | 0.96 | C3B—H6B | 0.969 (11) |
C5A—C6A | 1.5248 (14) | C4B—H7B | 1.021 (11) |
C5A—H6A | 0.97 | C4B—H8B | 1.021 (11) |
C5A—H7A | 0.97 | C4B—H9B | 1.021 (11) |
| | | |
C2A—N1A—H1A | 110.3 (9) | C5A—C6A—H8A | 109.47 (7) |
C2A—N1A—H2A | 112.5 (10) | C5A—C6A—H9A | 109.47 (7) |
H1A—N1A—H2A | 108.2 (13) | H8A—C6A—H9A | 109.5 |
C2A—N1A—H3A | 107.9 (9) | C5A—C6A—H10A | 109.47 (7) |
H1A—N1A—H3A | 112.7 (14) | H8A—C6A—H10A | 109.5 |
H2A—N1A—H3A | 105.1 (15) | H9A—C6A—H10A | 109.5 |
O1A—C1A—O2A | 125.96 (7) | C2B—N1B—H1B | 111.0 (8) |
O1A—C1A—C2A | 116.44 (6) | C2B—N1B—H2B | 110.2 (10) |
O2A—C1A—C2A | 117.55 (7) | H1B—N1B—H2B | 109.1 (13) |
N1A—C2A—C1A | 107.76 (6) | C2B—N1B—H3B | 108.7 (9) |
N1A—C2A—C3A | 110.14 (6) | H1B—N1B—H3B | 109.2 (15) |
C1A—C2A—C3A | 110.64 (6) | H2B—N1B—H3B | 108.6 (15) |
N1A—C2A—H4A | 109.43 (4) | O1B—C1B—O2B | 125.87 (8) |
C1A—C2A—H4A | 109.43 (4) | O1B—C1B—C2B | 117.14 (6) |
C3A—C2A—H4A | 109.43 (5) | O2B—C1B—C2B | 116.87 (7) |
C4A—C3A—C5A | 111.65 (9) | N1B—C2B—C1B | 109.13 (6) |
C4A—C3A—C2A | 110.73 (7) | N1B—C2B—C3B | 111.03 (6) |
C5A—C3A—C2A | 112.02 (7) | C1B—C2B—C3B | 108.33 (7) |
C4A—C3A—H5A | 107.39 (8) | N1B—C2B—H4B | 109.44 (5) |
C5A—C3A—H5A | 107.39 (6) | C1B—C2B—H4B | 109.44 (4) |
C2A—C3A—H5A | 107.39 (5) | C3B—C2B—H4B | 109.44 (5) |
C3A—C4A—H11A | 109.47 (5) | C4B—C3B—C2B | 114.49 (8) |
C3A—C4A—H12A | 109.47 (6) | C4B—C3B—H5B | 108.64 (7) |
H11A—C4A—H12A | 109.5 | C2B—C3B—H5B | 108.64 (5) |
C3A—C4A—H13A | 109.47 (8) | C4B—C3B—H6B | 108.64 (7) |
H11A—C4A—H13A | 109.5 | C2B—C3B—H6B | 108.64 (5) |
H12A—C4A—H13A | 109.5 | H5B—C3B—H6B | 107.6 |
C6A—C5A—C3A | 113.94 (10) | C3B—C4B—H7B | 109.47 (6) |
C6A—C5A—H6A | 108.77 (8) | C3B—C4B—H8B | 109.47 (7) |
C3A—C5A—H6A | 108.77 (6) | H7B—C4B—H8B | 109.5 |
C6A—C5A—H7A | 108.77 (6) | C3B—C4B—H9B | 109.47 (7) |
C3A—C5A—H7A | 108.8 | H7B—C4B—H9B | 109.5 |
H6A—C5A—H7A | 107.7 | H8B—C4B—H9B | 109.5 |
| | | |
O1A—C1A—C2A—N1A | −37.92 (9) | C4A—C3A—C5A—C6A | −56.15 (15) |
O2A—C1A—C2A—N1A | 144.65 (7) | C2A—C3A—C5A—C6A | 179.01 (9) |
O1A—C1A—C2A—C3A | 82.53 (8) | O1B—C1B—C2B—N1B | 31.73 (10) |
O2A—C1A—C2A—C3A | −94.89 (9) | O2B—C1B—C2B—N1B | −152.03 (7) |
N1A—C2A—C3A—C4A | −178.73 (9) | O1B—C1B—C2B—C3B | −89.27 (9) |
C1A—C2A—C3A—C4A | 62.24 (10) | O2B—C1B—C2B—C3B | 86.97 (9) |
N1A—C2A—C3A—C5A | −53.38 (10) | N1B—C2B—C3B—C4B | 62.94 (12) |
C1A—C2A—C3A—C5A | −172.41 (7) | C1B—C2B—C3B—C4B | −177.25 (9) |
(L3)
L-Isoleucine:D-Norvaline
top
Crystal data top
C6H13NO2·C5H11NO2 | F(000) = 544 |
Mr = 248.32 | Dx = 1.225 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
a = 29.0557 (7) Å | Cell parameters from 8192 reflections |
b = 4.7551 (1) Å | µ = 0.09 mm−1 |
c = 9.9398 (2) Å | T = 150 K |
β = 101.358 (1)° | Plate, colourless |
V = 1346.41 (5) Å3 | 0.65 × 0.60 × 0.20 mm |
Z = 4 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 6859 independent reflections |
Radiation source: fine-focus sealed tube | 6684 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω scans | θmax = 40.4°, θmin = 3.9° |
Absorption correction: multi-scan Sheldrick (1996) | h = −52→49 |
Tmin = 0.942, Tmax = 0.982 | k = −8→7 |
12203 measured reflections | l = −17→17 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.097 | Calculated w = 1/[σ2(Fo2) + (0.048P)2 + 0.357P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
6859 reflections | Δρmax = 0.59 e Å−3 |
190 parameters | Δρmin = −0.42 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
O1A | 0.20897 (2) | −0.14181 (12) | 0.52846 (5) | 0.01630 (9) | |
O2A | 0.17753 (2) | 0.14834 (13) | 0.66383 (5) | 0.01934 (10) | |
N1A | 0.20009 (2) | 0.24988 (13) | 0.32940 (5) | 0.01378 (8) | |
H1A | 0.1988 (5) | 0.094 (4) | 0.2874 (13) | 0.021 (3)* | |
H2A | 0.1954 (5) | 0.383 (3) | 0.2674 (14) | 0.023 (3)* | |
H3A | 0.2306 (5) | 0.291 (3) | 0.3772 (14) | 0.024 (3)* | |
C1A | 0.18622 (2) | 0.07260 (13) | 0.54954 (6) | 0.01264 (9) | |
C2A | 0.16555 (2) | 0.25143 (14) | 0.42301 (6) | 0.01207 (9) | |
H4A | 0.16119 (6) | 0.442 (3) | 0.4516 (4) | 0.014* | |
C3A | 0.11786 (2) | 0.13134 (15) | 0.34840 (6) | 0.01502 (10) | |
H5A | 0.12249 (7) | −0.066 (3) | 0.3310 (2) | 0.018* | |
C4A | 0.08169 (3) | 0.1502 (4) | 0.44034 (9) | 0.0405 (3) | |
H6A | 0.0946 (2) | 0.064 (3) | 0.5300 (11) | 0.061* | |
H7A | 0.0529 (4) | 0.050 (2) | 0.3969 (8) | 0.061* | |
H8A | 0.0741 (3) | 0.349 (2) | 0.4535 (10) | 0.061* | |
C5A | 0.10068 (3) | 0.2746 (2) | 0.20910 (9) | 0.0276 (2) | |
H9A | 0.09774 (4) | 0.482 (2) | 0.2246 (2) | 0.033* | |
H10A | 0.1250 (3) | 0.2480 (4) | 0.1512 (7) | 0.033* | |
C6A | 0.05388 (3) | 0.1654 (3) | 0.12998 (9) | 0.0309 (2) | |
H11A | 0.0475 (2) | 0.248 (2) | 0.0354 (11) | 0.046* | |
H12A | 0.0282 (3) | 0.221 (2) | 0.1788 (8) | 0.046* | |
H13A | 0.05511 (13) | −0.045 (2) | 0.1236 (10) | 0.046* | |
O1B | 0.21493 (2) | 1.02876 (11) | 1.02735 (5) | 0.01603 (9) | |
O2B | 0.18748 (2) | 0.74587 (13) | 1.17365 (5) | 0.01961 (10) | |
N1B | 0.19683 (2) | 0.64742 (13) | 0.82303 (5) | 0.01399 (8) | |
H1B | 0.1935 (5) | 0.831 (4) | 0.7834 (15) | 0.029 (4)* | |
H2B | 0.1873 (5) | 0.500 (3) | 0.7605 (14) | 0.022 (3)* | |
H3B | 0.2269 (5) | 0.628 (4) | 0.8636 (14) | 0.027 (3)* | |
C1B | 0.19343 (2) | 0.81508 (13) | 1.05548 (6) | 0.01264 (9) | |
C2B | 0.16937 (2) | 0.63188 (14) | 0.93505 (6) | 0.01266 (9) | |
H4B | 0.16855 (2) | 0.442 (3) | 0.9650 (4) | 0.015* | |
C3B | 0.11909 (2) | 0.7376 (2) | 0.88579 (7) | 0.01690 (10) | |
H5B | 0.1027 (2) | 0.7294 (2) | 0.9630 (7) | 0.020* | |
H6B | 0.12038 (3) | 0.9357 (19) | 0.8590 (3) | 0.020* | |
C4B | 0.09033 (3) | 0.5757 (2) | 0.76572 (10) | 0.0288 (2) | |
H7B | 0.08936 (3) | 0.385 (2) | 0.7896 (3) | 0.035* | |
H8B | 0.1051 (2) | 0.5885 (3) | 0.6901 (9) | 0.035* | |
C5B | 0.04021 (3) | 0.6876 (3) | 0.72515 (12) | 0.0334 (2) | |
H9B | 0.0230 (2) | 0.5782 (19) | 0.6468 (11) | 0.050* | |
H10B | 0.04104 (3) | 0.887 (2) | 0.6989 (11) | 0.050* | |
H11B | 0.0242 (2) | 0.669 (2) | 0.8036 (9) | 0.050* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0173 (2) | 0.0148 (2) | 0.0156 (2) | 0.00292 (15) | 0.0002 (2) | 0.0009 (2) |
O2A | 0.0299 (2) | 0.0178 (2) | 0.0105 (2) | 0.0013 (2) | 0.0043 (2) | −0.0007 (2) |
N1A | 0.0143 (2) | 0.0156 (2) | 0.0110 (2) | −0.0023 (2) | 0.00123 (15) | 0.0014 (2) |
C1A | 0.0145 (2) | 0.0125 (2) | 0.0101 (2) | −0.0013 (2) | 0.0002 (2) | 0.0004 (2) |
C2A | 0.0136 (2) | 0.0117 (2) | 0.0103 (2) | −0.0003 (2) | 0.0007 (2) | 0.0006 (2) |
C3A | 0.0131 (2) | 0.0177 (3) | 0.0134 (2) | −0.0018 (2) | 0.0003 (2) | −0.0001 (2) |
C4A | 0.0172 (3) | 0.0826 (9) | 0.0224 (3) | −0.0084 (4) | 0.0059 (3) | −0.0071 (5) |
C5A | 0.0226 (3) | 0.0326 (4) | 0.0227 (3) | −0.0059 (3) | −0.0076 (3) | 0.0092 (3) |
C6A | 0.0179 (3) | 0.0488 (5) | 0.0222 (3) | −0.0024 (3) | −0.0058 (2) | −0.0009 (4) |
O1B | 0.0185 (2) | 0.0138 (2) | 0.0151 (2) | −0.00301 (15) | 0.0016 (2) | 0.0002 (2) |
O2B | 0.0311 (3) | 0.0175 (2) | 0.0106 (2) | −0.0025 (2) | 0.0050 (2) | 0.0004 (2) |
N1B | 0.0156 (2) | 0.0155 (2) | 0.0107 (2) | 0.0013 (2) | 0.00217 (15) | −0.0010 (2) |
C1B | 0.0149 (2) | 0.0119 (2) | 0.0106 (2) | 0.0008 (2) | 0.0012 (2) | −0.0002 (2) |
C2B | 0.0148 (2) | 0.0119 (2) | 0.0111 (2) | 0.0001 (2) | 0.0021 (2) | 0.0000 (2) |
C3B | 0.0144 (2) | 0.0178 (3) | 0.0178 (2) | 0.0016 (2) | 0.0016 (2) | −0.0023 (2) |
C4B | 0.0198 (3) | 0.0294 (4) | 0.0320 (4) | 0.0034 (3) | −0.0073 (3) | −0.0100 (3) |
C5B | 0.0171 (3) | 0.0423 (5) | 0.0372 (4) | 0.0012 (3) | −0.0037 (3) | −0.0004 (4) |
Geometric parameters (Å, º) top
O1A—C1A | 1.2551 (8) | C6A—H13A | 1.002 (10) |
O2A—C1A | 1.2636 (8) | O1B—C1B | 1.2530 (8) |
N1A—C2A | 1.4968 (8) | O2B—C1B | 1.2640 (7) |
N1A—H1A | 0.85 (2) | N1B—C2B | 1.4938 (8) |
N1A—H2A | 0.876 (15) | N1B—H1B | 0.95 (2) |
N1A—H3A | 0.939 (14) | N1B—H2B | 0.941 (15) |
C1A—C2A | 1.5388 (8) | N1B—H3B | 0.892 (14) |
C2A—C3A | 1.5464 (8) | C1B—C2B | 1.5333 (9) |
C2A—H4A | 0.966 (13) | C2B—C3B | 1.5314 (9) |
C3A—C4A | 1.5253 (10) | C2B—H4B | 0.953 (13) |
C3A—C5A | 1.5356 (10) | C3B—C4B | 1.5240 (11) |
C3A—H5A | 0.967 (14) | C3B—H5B | 0.981 (9) |
C4A—H6A | 0.985 (11) | C3B—H6B | 0.981 (9) |
C4A—H7A | 0.985 (11) | C4B—C5B | 1.5279 (12) |
C4A—H8A | 0.985 (11) | C4B—H7B | 0.938 (11) |
C5A—C6A | 1.5218 (11) | C4B—H8B | 0.938 (11) |
C5A—H9A | 1.004 (11) | C5B—H9B | 0.987 (11) |
C5A—H10A | 1.004 (11) | C5B—H10B | 0.987 (11) |
C6A—H11A | 1.002 (10) | C5B—H11B | 0.987 (10) |
C6A—H12A | 1.002 (10) | | |
| | | |
C2A—N1A—H1A | 109.9 (9) | C5A—C6A—H13A | 109.47 (6) |
C2A—N1A—H2A | 113.8 (9) | H11A—C6A—H13A | 109.5 |
H1A—N1A—H2A | 107.5 (13) | H12A—C6A—H13A | 109.5 |
C2A—N1A—H3A | 111.4 (8) | C2B—N1B—H1B | 109.1 (9) |
H1A—N1A—H3A | 112.1 (13) | C2B—N1B—H2B | 108.9 (8) |
H2A—N1A—H3A | 101.9 (13) | H1B—N1B—H2B | 114.6 (12) |
O1A—C1A—O2A | 125.92 (6) | C2B—N1B—H3B | 106.1 (9) |
O1A—C1A—C2A | 116.49 (5) | H1B—N1B—H3B | 107.1 (15) |
O2A—C1A—C2A | 117.54 (6) | H2B—N1B—H3B | 110.8 (13) |
N1A—C2A—C1A | 107.69 (5) | O1B—C1B—O2B | 125.73 (6) |
N1A—C2A—C3A | 110.31 (5) | O1B—C1B—C2B | 117.20 (5) |
C1A—C2A—C3A | 110.88 (5) | O2B—C1B—C2B | 116.93 (6) |
N1A—C2A—H4A | 109.31 (4) | N1B—C2B—C3B | 111.18 (5) |
C1A—C2A—H4A | 109.31 (3) | N1B—C2B—C1B | 109.00 (5) |
C3A—C2A—H4A | 109.31 (4) | C3B—C2B—C1B | 108.82 (5) |
C4A—C3A—C5A | 111.97 (7) | N1B—C2B—H4B | 109.27 (4) |
C4A—C3A—C2A | 110.43 (6) | C3B—C2B—H4B | 109.27 (4) |
C5A—C3A—C2A | 111.72 (6) | C1B—C2B—H4B | 109.27 (3) |
C4A—C3A—H5A | 107.49 (7) | C4B—C3B—C2B | 115.22 (6) |
C5A—C3A—H5A | 107.49 (5) | C4B—C3B—H5B | 108.47 (5) |
C2A—C3A—H5A | 107.49 (4) | C2B—C3B—H5B | 108.47 (3) |
C3A—C4A—H6A | 109.47 (5) | C4B—C3B—H6B | 108.47 (5) |
C3A—C4A—H7A | 109.47 (5) | C2B—C3B—H6B | 108.47 (4) |
H6A—C4A—H7A | 109.5 | H5B—C3B—H6B | 107.5 |
C3A—C4A—H8A | 109.47 (7) | C3B—C4B—C5B | 112.21 (8) |
H6A—C4A—H8A | 109.5 | C3B—C4B—H7B | 109.16 (5) |
H7A—C4A—H8A | 109.5 | C5B—C4B—H7B | 109.16 (6) |
C6A—C5A—C3A | 114.41 (7) | C3B—C4B—H8B | 109.16 (5) |
C6A—C5A—H9A | 108.66 (6) | C5B—C4B—H8B | 109.16 (6) |
C3A—C5A—H9A | 108.66 (5) | H7B—C4B—H8B | 107.9 |
C6A—C5A—H10A | 108.66 (5) | C4B—C5B—H9B | 109.47 (6) |
C3A—C5A—H10A | 108.66 (4) | C4B—C5B—H10B | 109.47 (6) |
H9A—C5A—H10A | 107.6 | H9B—C5B—H10B | 109.5 |
C5A—C6A—H11A | 109.47 (5) | C4B—C5B—H11B | 109.47 (6) |
C5A—C6A—H12A | 109.47 (6) | H9B—C5B—H11B | 109.5 |
H11A—C6A—H12A | 109.5 | H10B—C5B—H11B | 109.5 |
| | | |
O1A—C1A—C2A—N1A | −36.77 (7) | C2A—C3A—C5A—C6A | 179.85 (8) |
O2A—C1A—C2A—N1A | 145.56 (6) | O1B—C1B—C2B—N1B | 31.33 (8) |
O1A—C1A—C2A—C3A | 84.01 (7) | O2B—C1B—C2B—N1B | −152.66 (6) |
O2A—C1A—C2A—C3A | −93.66 (7) | O1B—C1B—C2B—C3B | −90.08 (7) |
N1A—C2A—C3A—C4A | −176.34 (8) | O2B—C1B—C2B—C3B | 85.93 (7) |
C1A—C2A—C3A—C4A | 64.45 (9) | N1B—C2B—C3B—C4B | 60.00 (9) |
N1A—C2A—C3A—C5A | −51.02 (8) | C1B—C2B—C3B—C4B | −179.93 (7) |
C1A—C2A—C3A—C5A | −170.23 (6) | C2B—C3B—C4B—C5B | 178.31 (8) |
C4A—C3A—C5A—C6A | −55.69 (12) | | |
(L4)
L-Isoleucine:D-Norleucine
top
Crystal data top
C12H26N2O4 | F(000) = 576 |
Mr = 262.35 | Dx = 1.228 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.012 (2) Å | Cell parameters from 8192 reflections |
b = 4.7227 (9) Å | µ = 0.09 mm−1 |
c = 30.335 (6) Å | T = 150 K |
β = 98.38 (3)° | Plate, colourless |
V = 1419.1 (5) Å3 | 0.55 × 0.30 × 0.15 mm |
Z = 4 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 14651 independent reflections |
Radiation source: fine-focus sealed tube | 12393 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 40.4°, θmin = 3.4° |
Absorption correction: multi-scan Sheldrick (1996) | h = −18→13 |
Tmin = 0.951, Tmax = 0.986 | k = −8→8 |
25110 measured reflections | l = −54→49 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.118 | Calculated w = 1/[σ2(Fo2) + (0.0427P)2 + 0.2719P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max = 0.008 |
14651 reflections | Δρmax = 0.51 e Å−3 |
399 parameters | Δρmin = −0.26 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
O1A | 0.57731 (8) | 0.3733 (2) | 0.03982 (3) | 0.01622 (15) | |
O2A | 0.73624 (7) | 0.6764 (2) | 0.07098 (3) | 0.0190 (2) | |
N1A | 0.37984 (8) | 0.7489 (2) | 0.04661 (3) | 0.01321 (15) | |
H1A | 0.3439 (18) | 0.591 (5) | 0.0473 (6) | 0.024 (5)* | |
H2A | 0.3208 (16) | 0.886 (4) | 0.0510 (5) | 0.017 (4)* | |
H3A | 0.3986 (16) | 0.787 (4) | 0.0176 (6) | 0.024 (4)* | |
C1A | 0.61585 (10) | 0.5921 (2) | 0.06153 (3) | 0.0126 (2) | |
C2A | 0.50558 (9) | 0.7649 (3) | 0.07982 (3) | 0.0120 (2) | |
H4A | 0.5331 (5) | 0.953 (4) | 0.08317 (7) | 0.014* | |
C3A | 0.48050 (10) | 0.6476 (3) | 0.12537 (3) | 0.0146 (2) | |
H5A | 0.4680 (2) | 0.442 (4) | 0.12249 (6) | 0.018* | |
C4A | 0.60488 (12) | 0.7028 (4) | 0.16009 (4) | 0.0321 (4) | |
H6A | 0.6145 (8) | 0.902 (3) | 0.1653 (3) | 0.048* | |
H7A | 0.6835 (10) | 0.632 (3) | 0.1493 (2) | 0.048* | |
H8A | 0.5942 (6) | 0.609 (3) | 0.1873 (4) | 0.048* | |
C5A | 0.35324 (11) | 0.7742 (3) | 0.14042 (4) | 0.0205 (2) | |
H9A | 0.3627 (2) | 0.979 (3) | 0.14180 (4) | 0.025* | |
H10A | 0.2763 (9) | 0.7308 (6) | 0.1181 (3) | 0.025* | |
C6A | 0.32446 (12) | 0.6672 (3) | 0.18558 (4) | 0.0266 (2) | |
H11A | 0.3267 (12) | 0.469 (2) | 0.18591 (14) | 0.040* | |
H12A | 0.2391 (11) | 0.729 (2) | 0.1904 (2) | 0.040* | |
H13A | 0.3899 (10) | 0.737 (2) | 0.2081 (3) | 0.040* | |
O1B | −0.06680 (8) | 0.3525 (2) | 0.46575 (3) | 0.01550 (15) | |
O2B | −0.23338 (7) | 0.6571 (2) | 0.44202 (3) | 0.0189 (2) | |
N1B | 0.12231 (8) | 0.7276 (2) | 0.44920 (3) | 0.0133 (2) | |
H1B | 0.1562 (19) | 0.567 (5) | 0.4464 (6) | 0.027 (5)* | |
H2B | 0.1737 (16) | 0.870 (4) | 0.4416 (6) | 0.015 (4)* | |
H3B | 0.1147 (19) | 0.764 (5) | 0.4817 (7) | 0.041 (5)* | |
C1B | −0.11286 (10) | 0.5720 (2) | 0.44573 (3) | 0.0118 (2) | |
C2B | −0.01456 (9) | 0.7441 (2) | 0.42180 (3) | 0.0113 (2) | |
H4B | −0.0425 (5) | 0.932 (4) | 0.41990 (5) | 0.014* | |
C3B | −0.01275 (10) | 0.6275 (3) | 0.37431 (3) | 0.0148 (2) | |
H5B | 0.0019 (3) | 0.423 (4) | 0.37650 (5) | 0.018* | |
C4B | −0.14991 (12) | 0.6797 (4) | 0.34603 (4) | 0.0359 (4) | |
H6B | −0.1635 (6) | 0.880 (3) | 0.3416 (4) | 0.054* | |
H7B | −0.2203 (9) | 0.604 (3) | 0.3611 (3) | 0.054* | |
H8B | −0.1523 (5) | 0.588 (3) | 0.3175 (4) | 0.054* | |
C5B | 0.10115 (11) | 0.7570 (3) | 0.35235 (3) | 0.0207 (2) | |
H9B | 0.0884 (2) | 0.961 (3) | 0.35056 (4) | 0.025* | |
H10B | 0.1866 (10) | 0.7210 (5) | 0.3712 (2) | 0.025* | |
C6B | 0.10985 (12) | 0.6438 (3) | 0.30581 (4) | 0.0250 (2) | |
H11B | 0.1158 (11) | 0.438 (2) | 0.30679 (8) | 0.038* | |
H12B | 0.1896 (11) | 0.721 (2) | 0.2953 (2) | 0.038* | |
H13B | 0.0297 (10) | 0.700 (2) | 0.2857 (2) | 0.038* | |
O1C | 0.06759 (8) | 0.5400 (2) | 0.03168 (3) | 0.01510 (14) | |
O2C | 0.23620 (7) | 0.2430 (2) | 0.05654 (3) | 0.01771 (15) | |
N1C | −0.12253 (8) | 0.1766 (2) | 0.05200 (3) | 0.0129 (2) | |
H1C | −0.1598 (17) | 0.341 (4) | 0.0561 (6) | 0.018 (4)* | |
H2C | −0.181 (2) | 0.041 (5) | 0.0608 (7) | 0.032 (5)* | |
H3C | −0.1220 (14) | 0.149 (4) | 0.0222 (5) | 0.015 (3)* | |
C1C | 0.11430 (10) | 0.3220 (2) | 0.05172 (3) | 0.0119 (2) | |
C2C | 0.01808 (9) | 0.1480 (2) | 0.07577 (3) | 0.0117 (2) | |
H4C | 0.0442 (5) | −0.046 (4) | 0.07606 (3) | 0.014* | |
C3C | 0.03029 (10) | 0.2567 (3) | 0.12376 (3) | 0.0156 (2) | |
H5C | 0.1178 (11) | 0.2265 (4) | 0.1374 (2) | 0.019* | |
H6C | 0.0160 (2) | 0.450 (2) | 0.12287 (3) | 0.019* | |
C4C | −0.06530 (11) | 0.1248 (3) | 0.15284 (3) | 0.0188 (2) | |
H7C | −0.1562 (11) | 0.1779 (7) | 0.14159 (14) | 0.023* | |
H8C | −0.05917 (13) | −0.077 (3) | 0.15141 (4) | 0.023* | |
C5C | −0.03172 (12) | 0.2200 (3) | 0.20110 (3) | 0.0252 (2) | |
H9C | −0.02596 (15) | 0.424 (3) | 0.20195 (4) | 0.030* | |
H10C | 0.0555 (11) | 0.1459 (10) | 0.2133 (2) | 0.030* | |
C6C | −0.13517 (13) | 0.1242 (4) | 0.23011 (4) | 0.0290 (3) | |
H11C | −0.1050 (7) | 0.178 (2) | 0.2608 (3) | 0.043* | |
H12C | −0.1450 (9) | −0.080 (2) | 0.2282 (3) | 0.043* | |
H13C | −0.2214 (10) | 0.213 (2) | 0.2198 (3) | 0.043* | |
O1D | 0.42787 (8) | 0.5241 (2) | 0.46106 (3) | 0.01604 (15) | |
O2D | 0.26720 (7) | 0.2234 (2) | 0.43081 (3) | 0.0177 (2) | |
N1D | 0.62596 (8) | 0.1515 (2) | 0.45482 (3) | 0.0139 (2) | |
H1D | 0.6611 (16) | 0.327 (4) | 0.4528 (5) | 0.016 (4)* | |
H2D | 0.687 (2) | 0.018 (5) | 0.4478 (6) | 0.031 (5)* | |
H3D | 0.6124 (16) | 0.124 (5) | 0.4847 (6) | 0.026 (4)* | |
C1D | 0.38825 (10) | 0.3031 (2) | 0.44027 (3) | 0.0122 (2) | |
C2D | 0.49752 (9) | 0.1216 (3) | 0.42342 (3) | 0.0122 (2) | |
H4D | 0.4708 (5) | −0.067 (4) | 0.42251 (4) | 0.015* | |
C3D | 0.52239 (10) | 0.2135 (3) | 0.37671 (3) | 0.0163 (2) | |
H5D | 0.5325 (2) | 0.413 (2) | 0.37625 (3) | 0.020* | |
H6D | 0.6042 (10) | 0.1315 (10) | 0.37055 (8) | 0.020* | |
C4D | 0.40807 (11) | 0.1269 (3) | 0.34040 (3) | 0.0215 (2) | |
H7D | 0.3249 (10) | 0.1967 (9) | 0.34805 (10) | 0.026* | |
H8D | 0.40265 (13) | −0.075 (3) | 0.33955 (4) | 0.026* | |
C5D | 0.42415 (12) | 0.2348 (3) | 0.29394 (4) | 0.0258 (2) | |
H9D | 0.3457 (10) | 0.1742 (8) | 0.2729 (3) | 0.031* | |
H10D | 0.42458 (12) | 0.442 (3) | 0.29441 (4) | 0.031* | |
C6D | 0.55160 (13) | 0.1324 (4) | 0.27712 (4) | 0.0343 (3) | |
H11D | 0.6301 (10) | 0.216 (2) | 0.2951 (4) | 0.052* | |
H12D | 0.5493 (6) | 0.189 (3) | 0.2462 (4) | 0.052* | |
H13D | 0.5569 (7) | −0.073 (3) | 0.2793 (4) | 0.052* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0166 (3) | 0.0156 (4) | 0.0173 (3) | 0.0006 (3) | 0.0054 (3) | −0.0029 (3) |
O2A | 0.0104 (3) | 0.0182 (4) | 0.0290 (4) | −0.0010 (3) | 0.0054 (3) | −0.0001 (3) |
N1A | 0.0110 (3) | 0.0145 (4) | 0.0144 (3) | 0.0013 (3) | 0.0030 (2) | 0.0021 (3) |
C1A | 0.0117 (4) | 0.0119 (4) | 0.0149 (4) | 0.0013 (3) | 0.0047 (3) | 0.0018 (3) |
C2A | 0.0098 (3) | 0.0119 (4) | 0.0146 (3) | 0.0002 (3) | 0.0032 (3) | 0.0006 (3) |
C3A | 0.0137 (4) | 0.0164 (4) | 0.0140 (3) | 0.0008 (4) | 0.0031 (3) | 0.0004 (4) |
C4A | 0.0186 (4) | 0.0600 (11) | 0.0169 (4) | −0.0019 (6) | −0.0003 (3) | 0.0016 (6) |
C5A | 0.0192 (4) | 0.0245 (5) | 0.0199 (4) | 0.0027 (4) | 0.0098 (3) | 0.0010 (4) |
C6A | 0.0250 (5) | 0.0404 (7) | 0.0162 (4) | −0.0048 (5) | 0.0090 (3) | −0.0015 (5) |
O1B | 0.0161 (3) | 0.0147 (4) | 0.0163 (3) | 0.0005 (3) | 0.0046 (3) | 0.0031 (3) |
O2B | 0.0109 (3) | 0.0178 (4) | 0.0294 (4) | 0.0007 (3) | 0.0075 (3) | 0.0011 (4) |
N1B | 0.0099 (3) | 0.0153 (4) | 0.0149 (3) | −0.0011 (3) | 0.0025 (2) | −0.0015 (3) |
C1B | 0.0111 (4) | 0.0115 (4) | 0.0135 (3) | −0.0013 (3) | 0.0042 (3) | −0.0018 (3) |
C2B | 0.0090 (3) | 0.0113 (4) | 0.0140 (3) | −0.0001 (3) | 0.0028 (3) | 0.0009 (3) |
C3B | 0.0135 (3) | 0.0177 (4) | 0.0133 (3) | −0.0016 (4) | 0.0029 (3) | −0.0009 (4) |
C4B | 0.0170 (4) | 0.0717 (11) | 0.0182 (4) | −0.0009 (6) | −0.0001 (3) | −0.0027 (6) |
C5B | 0.0216 (4) | 0.0261 (5) | 0.0157 (4) | −0.0065 (5) | 0.0079 (3) | −0.0027 (4) |
C6B | 0.0224 (5) | 0.0379 (6) | 0.0159 (4) | −0.0006 (5) | 0.0067 (3) | −0.0013 (5) |
O1C | 0.0151 (3) | 0.0138 (3) | 0.0171 (3) | 0.0011 (3) | 0.0043 (2) | 0.0025 (3) |
O2C | 0.0103 (3) | 0.0162 (4) | 0.0276 (4) | 0.0015 (3) | 0.0059 (2) | 0.0019 (3) |
N1C | 0.0103 (3) | 0.0149 (4) | 0.0138 (3) | −0.0014 (3) | 0.0027 (2) | −0.0010 (3) |
C1C | 0.0108 (3) | 0.0122 (4) | 0.0132 (3) | −0.0007 (3) | 0.0034 (3) | −0.0014 (3) |
C2C | 0.0104 (3) | 0.0116 (4) | 0.0136 (3) | −0.0003 (3) | 0.0033 (3) | −0.0002 (3) |
C3C | 0.0153 (4) | 0.0186 (5) | 0.0134 (3) | −0.0030 (4) | 0.0033 (3) | −0.0015 (4) |
C4C | 0.0191 (4) | 0.0237 (5) | 0.0147 (4) | −0.0035 (4) | 0.0057 (3) | −0.0011 (4) |
C5C | 0.0251 (5) | 0.0370 (6) | 0.0144 (4) | −0.0053 (5) | 0.0060 (3) | −0.0031 (4) |
C6C | 0.0280 (5) | 0.0445 (7) | 0.0161 (4) | −0.0034 (6) | 0.0087 (4) | 0.0005 (5) |
O1D | 0.0164 (3) | 0.0137 (3) | 0.0186 (3) | −0.0005 (3) | 0.0046 (3) | −0.0035 (3) |
O2D | 0.0106 (3) | 0.0179 (4) | 0.0253 (3) | −0.0007 (3) | 0.0049 (2) | −0.0024 (3) |
N1D | 0.0108 (3) | 0.0149 (4) | 0.0163 (3) | 0.0016 (3) | 0.0027 (2) | 0.0015 (3) |
C1D | 0.0110 (3) | 0.0130 (4) | 0.0132 (3) | 0.0002 (3) | 0.0040 (3) | 0.0013 (3) |
C2D | 0.0108 (3) | 0.0118 (4) | 0.0144 (3) | 0.0001 (4) | 0.0031 (3) | −0.0004 (3) |
C3D | 0.0138 (4) | 0.0217 (5) | 0.0142 (3) | −0.0012 (4) | 0.0051 (3) | −0.0008 (4) |
C4D | 0.0161 (4) | 0.0328 (6) | 0.0159 (4) | −0.0026 (4) | 0.0035 (3) | 0.0000 (4) |
C5D | 0.0227 (5) | 0.0398 (7) | 0.0154 (4) | 0.0013 (5) | 0.0039 (3) | 0.0017 (4) |
C6D | 0.0265 (5) | 0.0592 (9) | 0.0191 (4) | −0.0020 (6) | 0.0093 (4) | −0.0048 (6) |
Geometric parameters (Å, º) top
O1A—C1A | 1.2557 (14) | O1C—C1C | 1.2511 (14) |
O2A—C1A | 1.2620 (13) | O2C—C1C | 1.2642 (12) |
N1A—C2A | 1.4954 (13) | N1C—C2C | 1.4915 (13) |
N1A—H1A | 0.83 (2) | N1C—H1C | 0.88 (2) |
N1A—H2A | 0.90 (2) | N1C—H2C | 0.93 (2) |
N1A—H3A | 0.94 (2) | N1C—H3C | 0.915 (15) |
C1A—C2A | 1.5398 (14) | C1C—C2C | 1.5297 (14) |
C2A—C3A | 1.5429 (14) | C2C—C3C | 1.5315 (14) |
C2A—H4A | 0.93 (2) | C2C—H4C | 0.95 (2) |
C3A—C4A | 1.532 (2) | C3C—C4C | 1.5256 (15) |
C3A—C5A | 1.5357 (14) | C3C—H5C | 0.924 (11) |
C3A—H5A | 0.98 (2) | C3C—H6C | 0.924 (11) |
C4A—H6A | 0.956 (12) | C4C—C5C | 1.522 (2) |
C4A—H7A | 0.956 (12) | C4C—H7C | 0.958 (11) |
C4A—H8A | 0.956 (12) | C4C—H8C | 0.958 (12) |
C5A—C6A | 1.526 (2) | C5C—C6C | 1.522 (2) |
C5A—H9A | 0.970 (12) | C5C—H9C | 0.963 (12) |
C5A—H10A | 0.970 (12) | C5C—H10C | 0.963 (12) |
C6A—H11A | 0.935 (10) | C6C—H11C | 0.970 (11) |
C6A—H12A | 0.935 (10) | C6C—H12C | 0.970 (11) |
C6A—H13A | 0.935 (10) | C6C—H13C | 0.970 (11) |
O1B—C1B | 1.2549 (14) | O1D—C1D | 1.2534 (14) |
O2B—C1B | 1.2613 (12) | O2D—C1D | 1.2616 (12) |
N1B—C2B | 1.4977 (13) | N1D—C2D | 1.4915 (14) |
N1B—H1B | 0.84 (2) | N1D—H1D | 0.90 (2) |
N1B—H2B | 0.90 (2) | N1D—H2D | 0.92 (2) |
N1B—H3B | 1.02 (2) | N1D—H3D | 0.95 (2) |
C1B—C2B | 1.5376 (14) | C1D—C2D | 1.5352 (14) |
C2B—C3B | 1.5448 (14) | C2D—C3D | 1.5364 (14) |
C2B—H4B | 0.93 (2) | C2D—H4D | 0.93 (2) |
C3B—C4B | 1.529 (2) | C3D—C4D | 1.524 (2) |
C3B—C5B | 1.5296 (15) | C3D—H5D | 0.949 (12) |
C3B—H5B | 0.98 (2) | C3D—H6D | 0.949 (11) |
C4B—H6B | 0.964 (13) | C4D—C5D | 1.529 (2) |
C4B—H7B | 0.964 (13) | C4D—H7D | 0.956 (12) |
C4B—H8B | 0.964 (12) | C4D—H8D | 0.956 (12) |
C5B—C6B | 1.524 (2) | C5D—C6D | 1.521 (2) |
C5B—H9B | 0.973 (12) | C5D—H9D | 0.980 (12) |
C5B—H10B | 0.973 (12) | C5D—H10D | 0.980 (12) |
C6B—H11B | 0.972 (11) | C6D—H11D | 0.972 (12) |
C6B—H12B | 0.972 (11) | C6D—H12D | 0.972 (12) |
C6B—H13B | 0.972 (10) | C6D—H13D | 0.972 (12) |
| | | |
C2A—N1A—H1A | 110.8 (13) | C2C—N1C—H1C | 113.8 (11) |
C2A—N1A—H2A | 111.8 (11) | C2C—N1C—H2C | 112.6 (12) |
H1A—N1A—H2A | 110.3 (15) | H1C—N1C—H2C | 105.8 (16) |
C2A—N1A—H3A | 110.9 (10) | C2C—N1C—H3C | 108.9 (9) |
H1A—N1A—H3A | 109.8 (17) | H1C—N1C—H3C | 109.1 (15) |
H2A—N1A—H3A | 103.0 (15) | H2C—N1C—H3C | 106.4 (16) |
O1A—C1A—O2A | 126.08 (10) | O1C—C1C—O2C | 125.82 (10) |
O1A—C1A—C2A | 116.32 (9) | O1C—C1C—C2C | 117.19 (9) |
O2A—C1A—C2A | 117.55 (9) | O2C—C1C—C2C | 116.79 (9) |
N1A—C2A—C1A | 107.94 (8) | N1C—C2C—C1C | 109.67 (8) |
N1A—C2A—C3A | 110.76 (8) | N1C—C2C—C3C | 111.61 (8) |
C1A—C2A—C3A | 110.56 (9) | C1C—C2C—C3C | 107.75 (9) |
N1A—C2A—H4A | 109.18 (6) | N1C—C2C—H4C | 109.26 (6) |
C1A—C2A—H4A | 109.18 (6) | C1C—C2C—H4C | 109.26 (6) |
C3A—C2A—H4A | 109.18 (6) | C3C—C2C—H4C | 109.26 (6) |
C4A—C3A—C5A | 110.86 (9) | C4C—C3C—C2C | 116.28 (9) |
C4A—C3A—C2A | 109.43 (9) | C4C—C3C—H5C | 108.22 (6) |
C5A—C3A—C2A | 112.13 (9) | C2C—C3C—H5C | 108.22 (6) |
C4A—C3A—H5A | 108.09 (9) | C4C—C3C—H6C | 108.22 (7) |
C5A—C3A—H5A | 108.09 (6) | C2C—C3C—H6C | 108.22 (6) |
C2A—C3A—H5A | 108.09 (6) | H5C—C3C—H6C | 107.4 |
C3A—C4A—H6A | 109.47 (9) | C5C—C4C—C3C | 111.50 (10) |
C3A—C4A—H7A | 109.47 (7) | C5C—C4C—H7C | 109.33 (7) |
H6A—C4A—H7A | 109.5 | C3C—C4C—H7C | 109.33 (6) |
C3A—C4A—H8A | 109.47 (7) | C5C—C4C—H8C | 109.33 (8) |
H6A—C4A—H8A | 109.5 | C3C—C4C—H8C | 109.33 (7) |
H7A—C4A—H8A | 109.5 | H7C—C4C—H8C | 108.0 |
C6A—C5A—C3A | 114.27 (10) | C4C—C5C—C6C | 113.26 (10) |
C6A—C5A—H9A | 108.69 (7) | C4C—C5C—H9C | 108.92 (7) |
C3A—C5A—H9A | 108.69 (6) | C6C—C5C—H9C | 108.92 (8) |
C6A—C5A—H10A | 108.69 (7) | C4C—C5C—H10C | 108.92 (7) |
C3A—C5A—H10A | 108.69 (6) | C6C—C5C—H10C | 108.92 (7) |
H9A—C5A—H10A | 107.6 | H9C—C5C—H10C | 107.7 |
C5A—C6A—H11A | 109.47 (7) | C5C—C6C—H11C | 109.47 (7) |
C5A—C6A—H12A | 109.47 (7) | C5C—C6C—H12C | 109.47 (8) |
H11A—C6A—H12A | 109.5 | H11C—C6C—H12C | 109.5 |
C5A—C6A—H13A | 109.47 (7) | C5C—C6C—H13C | 109.47 (8) |
H11A—C6A—H13A | 109.5 | H11C—C6C—H13C | 109.5 |
H12A—C6A—H13A | 109.5 | H12C—C6C—H13C | 109.5 |
C2B—N1B—H1B | 110.0 (13) | C2D—N1D—H1D | 110.6 (10) |
C2B—N1B—H2B | 109.4 (10) | C2D—N1D—H2D | 108.9 (12) |
H1B—N1B—H2B | 113.2 (15) | H1D—N1D—H2D | 109.5 (16) |
C2B—N1B—H3B | 109.8 (11) | C2D—N1D—H3D | 111.6 (10) |
H1B—N1B—H3B | 109.7 (18) | H1D—N1D—H3D | 107.7 (16) |
H2B—N1B—H3B | 104.7 (16) | H2D—N1D—H3D | 108.6 (16) |
O1B—C1B—O2B | 125.86 (10) | O1D—C1D—O2D | 125.87 (10) |
O1B—C1B—C2B | 116.72 (9) | O1D—C1D—C2D | 116.35 (9) |
O2B—C1B—C2B | 117.35 (9) | O2D—C1D—C2D | 117.73 (9) |
N1B—C2B—C1B | 107.91 (8) | N1D—C2D—C1D | 108.92 (8) |
N1B—C2B—C3B | 111.40 (8) | N1D—C2D—C3D | 108.77 (8) |
C1B—C2B—C3B | 110.32 (9) | C1D—C2D—C3D | 111.61 (9) |
N1B—C2B—H4B | 109.06 (6) | N1D—C2D—H4D | 109.17 (6) |
C1B—C2B—H4B | 109.06 (6) | C1D—C2D—H4D | 109.17 (6) |
C3B—C2B—H4B | 109.06 (6) | C3D—C2D—H4D | 109.17 (7) |
C4B—C3B—C5B | 110.90 (10) | C4D—C3D—C2D | 112.64 (9) |
C4B—C3B—C2B | 109.53 (9) | C4D—C3D—H5D | 109.07 (8) |
C5B—C3B—C2B | 112.00 (9) | C2D—C3D—H5D | 109.07 (7) |
C4B—C3B—H5B | 108.10 (9) | C4D—C3D—H6D | 109.07 (6) |
C5B—C3B—H5B | 108.10 (7) | C2D—C3D—H6D | 109.07 (6) |
C2B—C3B—H5B | 108.10 (6) | H5D—C3D—H6D | 107.8 |
C3B—C4B—H6B | 109.47 (9) | C3D—C4D—C5D | 114.06 (10) |
C3B—C4B—H7B | 109.47 (7) | C3D—C4D—H7D | 108.74 (6) |
H6B—C4B—H7B | 109.5 | C5D—C4D—H7D | 108.74 (7) |
C3B—C4B—H8B | 109.47 (7) | C3D—C4D—H8D | 108.74 (8) |
H6B—C4B—H8B | 109.5 | C5D—C4D—H8D | 108.74 (8) |
H7B—C4B—H8B | 109.5 | H7D—C4D—H8D | 107.6 |
C6B—C5B—C3B | 114.22 (10) | C6D—C5D—C4D | 114.16 (11) |
C6B—C5B—H9B | 108.70 (8) | C6D—C5D—H9D | 108.72 (7) |
C3B—C5B—H9B | 108.70 (7) | C4D—C5D—H9D | 108.72 (7) |
C6B—C5B—H10B | 108.70 (7) | C6D—C5D—H10D | 108.72 (9) |
C3B—C5B—H10B | 108.70 (6) | C4D—C5D—H10D | 108.72 (8) |
H9B—C5B—H10B | 107.6 | H9D—C5D—H10D | 107.6 |
C5B—C6B—H11B | 109.47 (8) | C5D—C6D—H11D | 109.47 (7) |
C5B—C6B—H12B | 109.47 (7) | C5D—C6D—H12D | 109.47 (7) |
H11B—C6B—H12B | 109.5 | H11D—C6D—H12D | 109.5 |
C5B—C6B—H13B | 109.47 (7) | C5D—C6D—H13D | 109.47 (9) |
H11B—C6B—H13B | 109.5 | H11D—C6D—H13D | 109.5 |
H12B—C6B—H13B | 109.5 | H12D—C6D—H13D | 109.5 |
| | | |
O1A—C1A—C2A—N1A | −35.32 (12) | C4B—C3B—C5B—C6B | −58.8 (2) |
O2A—C1A—C2A—N1A | 147.19 (9) | C2B—C3B—C5B—C6B | 178.53 (10) |
O1A—C1A—C2A—C3A | 85.98 (11) | O1C—C1C—C2C—N1C | 30.36 (13) |
O2A—C1A—C2A—C3A | −91.51 (12) | O2C—C1C—C2C—N1C | −154.44 (9) |
N1A—C2A—C3A—C4A | −172.54 (11) | O1C—C1C—C2C—C3C | −91.31 (11) |
C1A—C2A—C3A—C4A | 67.85 (13) | O2C—C1C—C2C—C3C | 83.88 (12) |
N1A—C2A—C3A—C5A | −49.09 (13) | N1C—C2C—C3C—C4C | 55.33 (13) |
C1A—C2A—C3A—C5A | −168.70 (9) | C1C—C2C—C3C—C4C | 175.79 (10) |
C4A—C3A—C5A—C6A | −56.81 (15) | C2C—C3C—C4C—C5C | 172.52 (10) |
C2A—C3A—C5A—C6A | −179.45 (10) | C3C—C4C—C5C—C6C | 172.61 (11) |
O1B—C1B—C2B—N1B | −35.53 (12) | O1D—C1D—C2D—N1D | 31.26 (12) |
O2B—C1B—C2B—N1B | 147.28 (9) | O2D—C1D—C2D—N1D | −151.10 (9) |
O1B—C1B—C2B—C3B | 86.38 (11) | O1D—C1D—C2D—C3D | −88.85 (11) |
O2B—C1B—C2B—C3B | −90.81 (12) | O2D—C1D—C2D—C3D | 88.79 (12) |
N1B—C2B—C3B—C4B | −173.53 (11) | N1D—C2D—C3D—C4D | 166.58 (10) |
C1B—C2B—C3B—C4B | 66.65 (13) | C1D—C2D—C3D—C4D | −73.23 (13) |
N1B—C2B—C3B—C5B | −50.06 (13) | C2D—C3D—C4D—C5D | 175.50 (11) |
C1B—C2B—C3B—C5B | −169.88 (9) | C3D—C4D—C5D—C6D | 59.9 (2) |
(L5)
L-Isoleucine:
D-Methionine
top
Crystal data top
C11H24N2O4S | F(000) = 608 |
Mr = 280.38 | Dx = 1.292 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
a = 31.7681 (3) Å | Cell parameters from 8192 reflections |
b = 4.7170 (1) Å | µ = 0.23 mm−1 |
c = 10.0043 (1) Å | T = 150 K |
β = 105.914 (1)° | Plate, colourless |
V = 1441.69 (4) Å3 | 0.70 × 0.25 × 0.10 mm |
Z = 4 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 10115 independent reflections |
Radiation source: fine-focus sealed tube | 8127 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω scans | θmax = 49.7°, θmin = 2.1° |
Absorption correction: multi-scan Sheldrick (1996) | h = −60→65 |
Tmin = 0.849, Tmax = 0.977 | k = −9→7 |
18678 measured reflections | l = −20→21 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.103 | Calculated w = 1/[σ2(Fo2) + (0.0408P)2 + 0.0836P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.002 |
10115 reflections | Δρmax = 0.39 e Å−3 |
199 parameters | Δρmin = −0.41 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
O1A | 0.21236 (2) | −0.04905 (13) | 0.52140 (6) | 0.01519 (9) | |
O2A | 0.18353 (2) | 0.25353 (14) | 0.64543 (6) | 0.01743 (10) | |
N1A | 0.20339 (2) | 0.3287 (2) | 0.31447 (6) | 0.01293 (9) | |
H1A | 0.2021 (5) | 0.157 (4) | 0.2730 (16) | 0.023 (4)* | |
H2A | 0.1972 (5) | 0.469 (4) | 0.2451 (16) | 0.022 (4)* | |
H3A | 0.2302 (5) | 0.351 (4) | 0.3692 (15) | 0.021 (3)* | |
C1A | 0.19126 (2) | 0.16935 (14) | 0.53428 (7) | 0.01131 (10) | |
C2A | 0.17168 (2) | 0.3419 (2) | 0.40076 (6) | 0.01124 (9) | |
H4A | 0.16835 (6) | 0.528 (3) | 0.4242 (4) | 0.013* | |
C3A | 0.12662 (2) | 0.2209 (2) | 0.32049 (7) | 0.01389 (10) | |
H5A | 0.12979 (6) | 0.005 (4) | 0.31350 (14) | 0.017* | |
C4A | 0.09334 (3) | 0.2784 (3) | 0.40277 (10) | 0.0296 (2) | |
H6A | 0.1054 (2) | 0.212 (3) | 0.4999 (12) | 0.044* | |
H7A | 0.0658 (4) | 0.175 (2) | 0.3592 (9) | 0.044* | |
H8A | 0.0873 (3) | 0.485 (3) | 0.4025 (11) | 0.044* | |
C5A | 0.11051 (3) | 0.3393 (2) | 0.17198 (8) | 0.01999 (13) | |
H9A | 0.10841 (4) | 0.555 (2) | 0.17695 (9) | 0.024* | |
H10A | 0.1330 (3) | 0.2926 (6) | 0.1195 (6) | 0.024* | |
C6A | 0.06593 (3) | 0.2217 (3) | 0.09035 (10) | 0.0284 (2) | |
H11A | 0.0605 (2) | 0.270 (2) | −0.0063 (12) | 0.043* | |
H12A | 0.0434 (3) | 0.302 (2) | 0.1260 (9) | 0.043* | |
H13A | 0.06588 (13) | 0.019 (2) | 0.1001 (10) | 0.043* | |
S1B | 0.049904 (7) | 0.85919 (7) | 0.63701 (2) | 0.02460 (5) | |
O1B | 0.21691 (2) | 1.12247 (13) | 1.02232 (6) | 0.01442 (9) | |
O2B | 0.19106 (2) | 0.82313 (14) | 1.15532 (5) | 0.01765 (10) | |
N1B | 0.20126 (2) | 0.75061 (14) | 0.80964 (6) | 0.01227 (9) | |
H1B | 0.1996 (5) | 0.923 (4) | 0.7673 (16) | 0.024 (4)* | |
H2B | 0.1915 (5) | 0.622 (4) | 0.7417 (16) | 0.023 (4)* | |
H3B | 0.2286 (5) | 0.722 (4) | 0.8599 (16) | 0.025 (4)* | |
C1B | 0.19685 (2) | 0.90354 (14) | 1.04098 (6) | 0.01108 (9) | |
C2B | 0.17469 (2) | 0.7287 (2) | 0.91168 (6) | 0.01114 (9) | |
H4B | 0.17296 (4) | 0.534 (3) | 0.9375 (4) | 0.013* | |
C3B | 0.12835 (2) | 0.8464 (2) | 0.85005 (7) | 0.01527 (10) | |
H5B | 0.1117 (2) | 0.8176 (4) | 0.9157 (7) | 0.018* | |
H6B | 0.13027 (3) | 1.047 (2) | 0.8366 (2) | 0.018* | |
C4B | 0.10391 (3) | 0.7110 (2) | 0.71200 (9) | 0.02069 (14) | |
H7B | 0.10098 (4) | 0.504 (3) | 0.7266 (2) | 0.025* | |
H8B | 0.1216 (2) | 0.7351 (4) | 0.6447 (8) | 0.025* | |
C5B | 0.01913 (4) | 0.6806 (3) | 0.73896 (13) | 0.0339 (2) | |
H9B | −0.0106 (4) | 0.731 (2) | 0.7061 (10) | 0.051* | |
H10B | 0.0298 (3) | 0.735 (2) | 0.8327 (12) | 0.051* | |
H11B | 0.0221 (3) | 0.483 (3) | 0.7313 (11) | 0.051* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0183 (2) | 0.0132 (2) | 0.0132 (2) | 0.0035 (2) | 0.0027 (2) | 0.0016 (2) |
O2A | 0.0279 (3) | 0.0160 (2) | 0.0092 (2) | 0.0013 (2) | 0.0065 (2) | −0.0004 (2) |
N1A | 0.0153 (2) | 0.0136 (2) | 0.0098 (2) | −0.0021 (2) | 0.00333 (15) | 0.0009 (2) |
C1A | 0.0146 (2) | 0.0102 (2) | 0.0084 (2) | −0.0009 (2) | 0.0017 (2) | 0.0001 (2) |
C2A | 0.0148 (2) | 0.0100 (2) | 0.0087 (2) | 0.0000 (2) | 0.0028 (2) | 0.0000 (2) |
C3A | 0.0146 (2) | 0.0148 (3) | 0.0112 (2) | −0.0006 (2) | 0.0017 (2) | 0.0001 (2) |
C4A | 0.0165 (3) | 0.0534 (7) | 0.0201 (3) | −0.0014 (3) | 0.0069 (3) | −0.0047 (4) |
C5A | 0.0201 (3) | 0.0229 (3) | 0.0132 (2) | −0.0002 (3) | −0.0017 (2) | 0.0027 (3) |
C6A | 0.0203 (4) | 0.0401 (6) | 0.0192 (3) | −0.0008 (4) | −0.0039 (3) | −0.0014 (4) |
S1B | 0.01464 (7) | 0.03396 (12) | 0.02131 (8) | 0.00098 (8) | −0.00164 (6) | 0.00555 (9) |
O1B | 0.0166 (2) | 0.0125 (2) | 0.0131 (2) | −0.0035 (2) | 0.0024 (2) | −0.0004 (2) |
O2B | 0.0298 (3) | 0.0149 (2) | 0.0093 (2) | −0.0022 (2) | 0.0070 (2) | 0.0001 (2) |
N1B | 0.0138 (2) | 0.0140 (2) | 0.0089 (2) | 0.0012 (2) | 0.0030 (2) | −0.0009 (2) |
C1B | 0.0134 (2) | 0.0112 (3) | 0.0083 (2) | 0.0006 (2) | 0.0022 (2) | −0.0004 (2) |
C2B | 0.0137 (2) | 0.0107 (2) | 0.0086 (2) | −0.0009 (2) | 0.0025 (2) | −0.0008 (2) |
C3B | 0.0128 (2) | 0.0176 (3) | 0.0141 (2) | 0.0010 (2) | 0.0016 (2) | −0.0025 (2) |
C4B | 0.0154 (3) | 0.0255 (4) | 0.0173 (3) | 0.0018 (3) | −0.0020 (2) | −0.0059 (3) |
C5B | 0.0207 (4) | 0.0448 (7) | 0.0345 (5) | −0.0039 (4) | 0.0048 (4) | 0.0076 (5) |
Geometric parameters (Å, º) top
O1A—C1A | 1.2550 (9) | C6A—H13A | 0.962 (11) |
O2A—C1A | 1.2666 (9) | S1B—C5B | 1.8035 (12) |
N1A—C2A | 1.4968 (9) | S1B—C4B | 1.8136 (9) |
N1A—H1A | 0.90 (2) | O1B—C1B | 1.2541 (9) |
N1A—H2A | 0.94 (2) | O2B—C1B | 1.2655 (8) |
N1A—H3A | 0.885 (15) | N1B—C2B | 1.4958 (9) |
C1A—C2A | 1.5421 (9) | N1B—H1B | 0.91 (2) |
C2A—C3A | 1.5459 (10) | N1B—H2B | 0.90 (2) |
C2A—H4A | 0.92 (2) | N1B—H3B | 0.89 (2) |
C3A—C4A | 1.5318 (12) | C1B—C2B | 1.5327 (9) |
C3A—C5A | 1.5378 (10) | C2B—C3B | 1.5354 (10) |
C3A—H5A | 1.03 (2) | C2B—H4B | 0.96 (2) |
C4A—H6A | 0.992 (12) | C3B—C4B | 1.5263 (11) |
C4A—H7A | 0.992 (12) | C3B—H5B | 0.959 (11) |
C4A—H8A | 0.992 (12) | C3B—H6B | 0.959 (11) |
C5A—C6A | 1.5317 (13) | C4B—H7B | 0.996 (12) |
C5A—H9A | 1.021 (12) | C4B—H8B | 0.996 (12) |
C5A—H10A | 1.021 (11) | C5B—H9B | 0.941 (12) |
C6A—H11A | 0.962 (11) | C5B—H10B | 0.941 (12) |
C6A—H12A | 0.962 (11) | C5B—H11B | 0.941 (12) |
| | | |
C2A—N1A—H1A | 110.4 (10) | H11A—C6A—H13A | 109.5 |
C2A—N1A—H2A | 111.1 (10) | H12A—C6A—H13A | 109.5 |
H1A—N1A—H2A | 108.4 (14) | C5B—S1B—C4B | 100.61 (5) |
C2A—N1A—H3A | 109.0 (9) | C2B—N1B—H1B | 114.1 (10) |
H1A—N1A—H3A | 107.7 (16) | C2B—N1B—H2B | 109.1 (10) |
H2A—N1A—H3A | 110.2 (15) | H1B—N1B—H2B | 106.6 (14) |
O1A—C1A—O2A | 125.82 (7) | C2B—N1B—H3B | 104.5 (10) |
O1A—C1A—C2A | 116.37 (6) | H1B—N1B—H3B | 108.8 (16) |
O2A—C1A—C2A | 117.76 (6) | H2B—N1B—H3B | 113.9 (16) |
N1A—C2A—C1A | 107.60 (5) | O1B—C1B—O2B | 125.95 (7) |
N1A—C2A—C3A | 111.03 (5) | O1B—C1B—C2B | 116.87 (6) |
C1A—C2A—C3A | 110.56 (6) | O2B—C1B—C2B | 117.05 (6) |
N1A—C2A—H4A | 109.21 (4) | N1B—C2B—C1B | 108.93 (6) |
C1A—C2A—H4A | 109.21 (4) | N1B—C2B—C3B | 111.06 (5) |
C3A—C2A—H4A | 109.21 (4) | C1B—C2B—C3B | 108.20 (6) |
C4A—C3A—C5A | 111.03 (7) | N1B—C2B—H4B | 109.54 (4) |
C4A—C3A—C2A | 109.43 (6) | C1B—C2B—H4B | 109.54 (4) |
C5A—C3A—C2A | 112.53 (6) | C3B—C2B—H4B | 109.54 (4) |
C4A—C3A—H5A | 107.89 (6) | C4B—C3B—C2B | 113.95 (6) |
C5A—C3A—H5A | 107.89 (5) | C4B—C3B—H5B | 108.76 (5) |
C2A—C3A—H5A | 107.89 (4) | C2B—C3B—H5B | 108.76 (4) |
C3A—C4A—H6A | 109.47 (5) | C4B—C3B—H6B | 108.76 (5) |
C3A—C4A—H7A | 109.47 (5) | C2B—C3B—H6B | 108.76 (4) |
H6A—C4A—H7A | 109.5 | H5B—C3B—H6B | 107.7 |
C3A—C4A—H8A | 109.47 (6) | C3B—C4B—S1B | 113.70 (6) |
H6A—C4A—H8A | 109.5 | C3B—C4B—H7B | 108.82 (5) |
H7A—C4A—H8A | 109.5 | S1B—C4B—H7B | 108.82 (3) |
C6A—C5A—C3A | 113.42 (8) | C3B—C4B—H8B | 108.82 (5) |
C6A—C5A—H9A | 108.89 (6) | S1B—C4B—H8B | 108.82 (3) |
C3A—C5A—H9A | 108.89 (5) | H7B—C4B—H8B | 107.7 |
C6A—C5A—H10A | 108.89 (5) | S1B—C5B—H9B | 109.47 (4) |
C3A—C5A—H10A | 108.89 (4) | S1B—C5B—H10B | 109.47 (4) |
H9A—C5A—H10A | 107.7 | H9B—C5B—H10B | 109.5 |
C5A—C6A—H11A | 109.47 (5) | S1B—C5B—H11B | 109.47 (5) |
C5A—C6A—H12A | 109.47 (6) | H9B—C5B—H11B | 109.5 |
H11A—C6A—H12A | 109.5 | H10B—C5B—H11B | 109.5 |
C5A—C6A—H13A | 109.47 (6) | | |
| | | |
O1A—C1A—C2A—N1A | −36.03 (8) | C2A—C3A—C5A—C6A | 179.87 (8) |
O2A—C1A—C2A—N1A | 146.29 (7) | O1B—C1B—C2B—N1B | 32.74 (9) |
O1A—C1A—C2A—C3A | 85.37 (8) | O2B—C1B—C2B—N1B | −151.30 (7) |
O2A—C1A—C2A—C3A | −92.31 (8) | O1B—C1B—C2B—C3B | −88.11 (8) |
N1A—C2A—C3A—C4A | −171.55 (8) | O2B—C1B—C2B—C3B | 87.85 (8) |
C1A—C2A—C3A—C4A | 69.10 (9) | N1B—C2B—C3B—C4B | 54.73 (9) |
N1A—C2A—C3A—C5A | −47.60 (9) | C1B—C2B—C3B—C4B | 174.24 (7) |
C1A—C2A—C3A—C5A | −166.96 (6) | C2B—C3B—C4B—S1B | −178.07 (6) |
C4A—C3A—C5A—C6A | −57.08 (11) | C5B—S1B—C4B—C3B | −79.09 (9) |
(B1)
L-Isoleucine:D-Valine
top
Crystal data top
C6H13NO2·C5H11NO2 | F(000) = 272 |
Mr = 248.32 | Dx = 1.289 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.2528 (1) Å | Cell parameters from 6101 reflections |
b = 23.9809 (6) Å | µ = 0.10 mm−1 |
c = 5.4200 (1) Å | T = 150 K |
β = 110.420 (1)° | Plate, colourless |
V = 639.84 (2) Å3 | 0.65 × 0.60 × 0.10 mm |
Z = 2 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 6854 independent reflections |
Radiation source: fine-focus sealed tube | 6220 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ω scans | θmax = 40.3°, θmin = 3.4° |
Absorption correction: multi-scan Sheldrick (1996) | h = −9→9 |
Tmin = 0.939, Tmax = 0.990 | k = −43→43 |
10296 measured reflections | l = −9→9 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.111 | Calculated w = 1/[σ2(Fo2) + (0.039P)2 + 0.1323P] where P = (Fo2 + 2Fc2)/3 |
S = 1.14 | (Δ/σ)max = −0.001 |
6854 reflections | Δρmax = 0.37 e Å−3 |
191 parameters | Δρmin = −0.25 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
O1A | 0.8903 (2) | 0.22269 (4) | 0.59890 (14) | 0.01742 (14) | |
O2A | 0.4438 (2) | 0.20401 (4) | 0.4632 (2) | 0.01708 (13) | |
N1A | 0.9007 (2) | 0.22898 (4) | 0.1102 (2) | 0.01386 (13) | |
H2A | 0.888 (4) | 0.2268 (8) | −0.071 (4) | 0.022 (4)* | |
H3A | 0.889 (4) | 0.2642 (8) | 0.142 (4) | 0.016 (4)* | |
H1A | 1.059 (4) | 0.2167 (8) | 0.219 (4) | 0.019 (4)* | |
C1A | 0.6663 (2) | 0.20966 (4) | 0.4264 (2) | 0.01249 (14) | |
C2A | 0.6661 (2) | 0.19912 (4) | 0.1459 (2) | 0.01233 (14) | |
H4A | 0.489 (3) | 0.2156 (3) | 0.014 (2) | 0.015* | |
C3A | 0.6767 (2) | 0.13645 (4) | 0.0817 (2) | 0.01466 (15) | |
H5A | 0.7435 (13) | 0.13369 (6) | −0.068 (3) | 0.018* | |
C4A | 0.8768 (2) | 0.10439 (5) | 0.3132 (2) | 0.0215 (2) | |
H6A | 1.045 (3) | 0.1252 (4) | 0.3831 (19) | 0.032* | |
H7A | 0.913 (2) | 0.0681 (5) | 0.2531 (10) | 0.032* | |
H8A | 0.7989 (15) | 0.0996 (5) | 0.450 (2) | 0.032* | |
C5A | 0.3918 (2) | 0.11065 (5) | −0.0075 (3) | 0.0225 (2) | |
H9A | 0.3326 (10) | 0.10831 (6) | 0.140 (2) | 0.027* | |
H10A | 0.2685 (19) | 0.1346 (4) | −0.136 (2) | 0.027* | |
C6A | 0.3818 (3) | 0.05255 (6) | −0.1264 (3) | 0.0336 (3) | |
H11A | 0.199 (3) | 0.0393 (3) | −0.188 (3) | 0.050* | |
H12A | 0.493 (3) | 0.0277 (4) | 0.005 (2) | 0.050* | |
H13A | 0.447 (3) | 0.05435 (13) | −0.270 (3) | 0.050* | |
O1B | 0.3033 (2) | 0.32034 (4) | 0.13077 (15) | 0.01766 (14) | |
O2B | 0.7500 (2) | 0.33844 (3) | 0.2660 (2) | 0.01739 (14) | |
N1B | 0.2935 (2) | 0.31423 (4) | 0.6203 (2) | 0.01439 (13) | |
H2B | 0.291 (4) | 0.3171 (9) | 0.783 (4) | 0.027 (5)* | |
H1B | 0.131 (4) | 0.3273 (9) | 0.512 (4) | 0.024 (4)* | |
H3B | 0.305 (4) | 0.2782 (9) | 0.587 (4) | 0.028 (5)* | |
C1B | 0.5272 (2) | 0.33311 (4) | 0.3032 (2) | 0.01265 (14) | |
C2B | 0.5281 (2) | 0.34390 (4) | 0.5837 (2) | 0.01315 (14) | |
H4B | 0.686 (3) | 0.3293 (3) | 0.702 (2) | 0.016* | |
C3B | 0.5175 (2) | 0.40683 (4) | 0.6446 (2) | 0.0179 (2) | |
H5B | 0.4561 (12) | 0.41015 (8) | 0.795 (3) | 0.021* | |
C4B | 0.8006 (3) | 0.43227 (7) | 0.7244 (3) | 0.0331 (3) | |
H6B | 0.926 (2) | 0.4112 (5) | 0.874 (3) | 0.050* | |
H7B | 0.7936 (7) | 0.4716 (6) | 0.776 (3) | 0.050* | |
H8B | 0.8658 (17) | 0.4305 (6) | 0.574 (3) | 0.050* | |
C5B | 0.3160 (3) | 0.43878 (5) | 0.4146 (3) | 0.0251 (2) | |
H9B | 0.145 (3) | 0.4198 (4) | 0.356 (2) | 0.038* | |
H10B | 0.3846 (16) | 0.4409 (5) | 0.273 (2) | 0.038* | |
H11B | 0.292 (2) | 0.4756 (6) | 0.4708 (11) | 0.038* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0159 (3) | 0.0258 (4) | 0.0107 (3) | −0.0034 (3) | 0.0048 (2) | −0.0027 (2) |
O2A | 0.0142 (3) | 0.0233 (3) | 0.0165 (3) | 0.0008 (3) | 0.0089 (2) | −0.0002 (3) |
N1A | 0.0151 (3) | 0.0174 (3) | 0.0102 (3) | −0.0028 (3) | 0.0059 (2) | −0.0008 (2) |
C1A | 0.0139 (3) | 0.0144 (4) | 0.0106 (3) | 0.0009 (3) | 0.0060 (3) | 0.0002 (3) |
C2A | 0.0129 (3) | 0.0151 (3) | 0.0098 (3) | −0.0001 (3) | 0.0050 (2) | 0.0000 (3) |
C3A | 0.0163 (4) | 0.0150 (4) | 0.0138 (4) | −0.0004 (3) | 0.0066 (3) | −0.0020 (3) |
C4A | 0.0217 (5) | 0.0203 (5) | 0.0216 (5) | 0.0036 (4) | 0.0064 (4) | 0.0015 (4) |
C5A | 0.0188 (4) | 0.0224 (5) | 0.0252 (5) | −0.0047 (4) | 0.0064 (4) | −0.0054 (4) |
C6A | 0.0389 (7) | 0.0207 (5) | 0.0336 (6) | −0.0069 (5) | 0.0033 (5) | −0.0052 (5) |
O1B | 0.0167 (3) | 0.0258 (4) | 0.0113 (3) | −0.0040 (3) | 0.0058 (2) | −0.0027 (2) |
O2B | 0.0160 (3) | 0.0229 (4) | 0.0164 (3) | 0.0011 (3) | 0.0096 (2) | 0.0003 (3) |
N1B | 0.0165 (3) | 0.0171 (3) | 0.0108 (3) | −0.0026 (3) | 0.0064 (3) | −0.0008 (3) |
C1B | 0.0155 (3) | 0.0131 (3) | 0.0108 (3) | 0.0008 (3) | 0.0065 (3) | −0.0004 (3) |
C2B | 0.0137 (3) | 0.0171 (4) | 0.0092 (3) | −0.0011 (3) | 0.0048 (2) | −0.0013 (3) |
C3B | 0.0207 (4) | 0.0181 (4) | 0.0179 (4) | −0.0037 (3) | 0.0106 (3) | −0.0046 (3) |
C4B | 0.0284 (6) | 0.0336 (7) | 0.0393 (7) | −0.0162 (5) | 0.0143 (5) | −0.0161 (6) |
C5B | 0.0315 (6) | 0.0179 (5) | 0.0295 (6) | 0.0041 (4) | 0.0151 (5) | 0.0040 (4) |
Geometric parameters (Å, º) top
O1A—C1A | 1.2604 (12) | C6A—H13A | 0.956 (14) |
O2A—C1A | 1.2600 (12) | O1B—C1B | 1.2585 (12) |
N1A—C2A | 1.4947 (12) | O2B—C1B | 1.2614 (12) |
N1A—H2A | 0.96 (2) | N1B—C2B | 1.4944 (13) |
N1A—H3A | 0.87 (2) | N1B—H2B | 0.89 (2) |
N1A—H1A | 0.89 (2) | N1B—H1B | 0.91 (2) |
C1A—C2A | 1.5410 (13) | N1B—H3B | 0.89 (2) |
C2A—C3A | 1.5478 (13) | C1B—C2B | 1.5408 (13) |
C2A—H4A | 1.03 (2) | C2B—C3B | 1.5497 (14) |
C3A—C4A | 1.533 (2) | C2B—H4B | 0.92 (2) |
C3A—C5A | 1.5334 (15) | C3B—C4B | 1.524 (2) |
C3A—H5A | 0.99 (2) | C3B—C5B | 1.530 (2) |
C4A—H6A | 0.970 (13) | C3B—H5B | 0.98 (2) |
C4A—H7A | 0.970 (13) | C4B—H6B | 0.99 (2) |
C4A—H8A | 0.970 (13) | C4B—H7B | 0.99 (2) |
C5A—C6A | 1.528 (2) | C4B—H8B | 0.99 (2) |
C5A—H9A | 0.957 (15) | C5B—H9B | 0.957 (14) |
C5A—H10A | 0.957 (15) | C5B—H10B | 0.957 (14) |
C6A—H11A | 0.956 (14) | C5B—H11B | 0.957 (14) |
C6A—H12A | 0.956 (14) | | |
| | | |
C2A—N1A—H2A | 109.8 (11) | C5A—C6A—H13A | 109.47 (8) |
C2A—N1A—H3A | 108.8 (12) | H11A—C6A—H13A | 109.5 |
H2A—N1A—H3A | 105.6 (18) | H12A—C6A—H13A | 109.5 |
C2A—N1A—H1A | 112.2 (12) | C2B—N1B—H2B | 113.2 (13) |
H2A—N1A—H1A | 112.2 (16) | C2B—N1B—H1B | 112.5 (12) |
H3A—N1A—H1A | 108.0 (18) | H2B—N1B—H1B | 106.1 (17) |
O2A—C1A—O1A | 125.92 (9) | C2B—N1B—H3B | 108.5 (14) |
O2A—C1A—C2A | 117.23 (8) | H2B—N1B—H3B | 108 (2) |
O1A—C1A—C2A | 116.85 (8) | H1B—N1B—H3B | 108.8 (19) |
N1A—C2A—C1A | 109.40 (7) | O1B—C1B—O2B | 125.78 (9) |
N1A—C2A—C3A | 109.89 (7) | O1B—C1B—C2B | 116.99 (8) |
C1A—C2A—C3A | 113.16 (8) | O2B—C1B—C2B | 117.22 (8) |
N1A—C2A—H4A | 108.08 (5) | N1B—C2B—C1B | 109.39 (7) |
C1A—C2A—H4A | 108.08 (5) | N1B—C2B—C3B | 110.06 (8) |
C3A—C2A—H4A | 108.08 (5) | C1B—C2B—C3B | 112.68 (8) |
C4A—C3A—C5A | 111.75 (9) | N1B—C2B—H4B | 108.20 (5) |
C4A—C3A—C2A | 111.79 (8) | C1B—C2B—H4B | 108.20 (5) |
C5A—C3A—C2A | 110.79 (8) | C3B—C2B—H4B | 108.20 (5) |
C4A—C3A—H5A | 107.42 (6) | C4B—C3B—C5B | 111.10 (11) |
C5A—C3A—H5A | 107.42 (6) | C4B—C3B—C2B | 110.27 (10) |
C2A—C3A—H5A | 107.42 (5) | C5B—C3B—C2B | 112.36 (9) |
C3A—C4A—H6A | 109.47 (6) | C4B—C3B—H5B | 107.63 (7) |
C3A—C4A—H7A | 109.47 (6) | C5B—C3B—H5B | 107.64 (6) |
H6A—C4A—H7A | 109.5 | C2B—C3B—H5B | 107.64 (5) |
C3A—C4A—H8A | 109.47 (6) | C3B—C4B—H6B | 109.47 (9) |
H6A—C4A—H8A | 109.5 | C3B—C4B—H7B | 109.47 (7) |
H7A—C4A—H8A | 109.5 | H6B—C4B—H7B | 109.5 |
C6A—C5A—C3A | 112.79 (11) | C3B—C4B—H8B | 109.47 (7) |
C6A—C5A—H9A | 109.03 (8) | H6B—C4B—H8B | 109.5 |
C3A—C5A—H9A | 109.03 (6) | H7B—C4B—H8B | 109.5 |
C6A—C5A—H10A | 109.03 (8) | C3B—C5B—H9B | 109.47 (6) |
C3A—C5A—H10A | 109.03 (6) | C3B—C5B—H10B | 109.47 (6) |
H9A—C5A—H10A | 107.8 | H9B—C5B—H10B | 109.5 |
C5A—C6A—H11A | 109.47 (8) | C3B—C5B—H11B | 109.47 (6) |
C5A—C6A—H12A | 109.47 (8) | H9B—C5B—H11B | 109.5 |
H11A—C6A—H12A | 109.5 | H10B—C5B—H11B | 109.5 |
| | | |
O2A—C1A—C2A—N1A | 157.01 (9) | C2A—C3A—C5A—C6A | 168.22 (10) |
O1A—C1A—C2A—N1A | −23.60 (12) | O1B—C1B—C2B—N1B | 23.92 (12) |
O2A—C1A—C2A—C3A | −80.10 (11) | O2B—C1B—C2B—N1B | −156.83 (8) |
O1A—C1A—C2A—C3A | 99.28 (10) | O1B—C1B—C2B—C3B | −98.84 (10) |
N1A—C2A—C3A—C4A | 80.72 (10) | O2B—C1B—C2B—C3B | 80.40 (11) |
C1A—C2A—C3A—C4A | −41.89 (11) | N1B—C2B—C3B—C4B | 155.56 (10) |
N1A—C2A—C3A—C5A | −153.91 (9) | C1B—C2B—C3B—C4B | −82.05 (12) |
C1A—C2A—C3A—C5A | 83.47 (10) | N1B—C2B—C3B—C5B | −79.91 (10) |
C4A—C3A—C5A—C6A | −66.40 (13) | C1B—C2B—C3B—C5B | 42.47 (12) |
(B2)
L-Isoleucine:D-Leucine
top
Crystal data top
C6H13NO2·C6H13NO2 | V = 355.16 (3) Å3 |
Mr = 262.35 | Z = 1 |
Triclinic, P1 | F(000) = 144 |
Hall symbol: P 1 | Dx = 1.227 Mg m−3 |
a = 5.1933 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 5.4064 (3) Å | Cell parameters from 1220 reflections |
c = 13.6968 (7) Å | µ = 0.09 mm−1 |
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 tube | 4082 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω scans | θmax = 40.6°, θmin = 3.0° |
Absorption correction: multi-scan Sheldrick (1996) | h = −7→9 |
Tmin = 0.982, Tmax = 0.990 | k = −9→8 |
5657 measured reflections | l = −23→24 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.134 | Calculated w = 1/[σ2(Fo2) + (0.0348P)2 + 0.086P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max = −0.006 |
4689 reflections | Δρmax = 0.59 e Å−3 |
201 parameters | Δρmin = −0.40 e Å−3 |
3 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
O1A | 1.0178 (3) | 0.6454 (2) | 0.54362 (10) | 0.0165 (2) | |
O2A | 0.5853 (2) | 0.5199 (2) | 0.57867 (10) | 0.0153 (2) | |
N1A | 1.0229 (3) | 0.1534 (3) | 0.53328 (11) | 0.0123 (2) | |
H1A | 1.202 (6) | 0.270 (5) | 0.557 (2) | 0.014 (6)* | |
H2A | 1.029 (7) | −0.020 (7) | 0.541 (3) | 0.030 (8)* | |
H3A | 0.989 (9) | 0.179 (8) | 0.464 (3) | 0.041 (9)* | |
C1A | 0.8048 (3) | 0.4791 (3) | 0.56787 (12) | 0.0118 (2) | |
C2A | 0.8136 (3) | 0.2029 (3) | 0.58754 (11) | 0.0113 (2) | |
H4A | 0.630 (5) | 0.071 (4) | 0.5611 (7) | 0.014* | |
C3A | 0.8831 (3) | 0.1687 (3) | 0.69866 (12) | 0.0136 (3) | |
H5A | 0.960 (2) | 0.011 (4) | 0.7044 (2) | 0.016* | |
C4A | 1.1104 (3) | 0.4169 (3) | 0.75451 (12) | 0.0189 (3) | |
H6A | 1.0352 (18) | 0.554 (3) | 0.7608 (12) | 0.028* | |
H7A | 1.263 (3) | 0.476 (2) | 0.7185 (10) | 0.028* | |
H8A | 1.176 (3) | 0.3760 (13) | 0.8191 (13) | 0.028* | |
C5A | 0.6183 (4) | 0.0893 (4) | 0.74578 (14) | 0.0215 (3) | |
H9A | 0.5548 (16) | 0.238 (4) | 0.74755 (14) | 0.026* | |
H10A | 0.473 (3) | −0.056 (3) | 0.7045 (10) | 0.026* | |
C6A | 0.6617 (5) | 0.0056 (5) | 0.8503 (2) | 0.0344 (5) | |
H11A | 0.726 (5) | −0.136 (5) | 0.8494 (3) | 0.052* | |
H12A | 0.492 (5) | −0.047 (5) | 0.8743 (10) | 0.052* | |
H13A | 0.794 (5) | 0.149 (4) | 0.8918 (11) | 0.052* | |
O1B | 0.3447 (3) | 0.1377 (2) | 0.37011 (10) | 0.0166 (2) | |
O2B | 0.7841 (2) | 0.2726 (2) | 0.34070 (10) | 0.0157 (2) | |
N1B | 0.3519 (3) | 0.6373 (3) | 0.38544 (11) | 0.0135 (2) | |
H1B | 0.164 (6) | 0.524 (6) | 0.365 (2) | 0.018 (6)* | |
H2B | 0.363 (6) | 0.788 (6) | 0.378 (2) | 0.019 (7)* | |
H3B | 0.419 (6) | 0.621 (6) | 0.450 (2) | 0.017 (6)* | |
C1B | 0.5594 (3) | 0.3070 (3) | 0.34688 (11) | 0.0113 (2) | |
C2B | 0.5377 (3) | 0.5762 (3) | 0.32302 (11) | 0.0110 (2) | |
H4B | 0.709 (5) | 0.704 (4) | 0.3362 (4) | 0.013* | |
C3B | 0.4115 (4) | 0.5682 (3) | 0.21343 (13) | 0.0164 (3) | |
H5B | 0.242 (4) | 0.413 (3) | 0.1980 (3) | 0.020* | |
H6B | 0.3601 (11) | 0.724 (3) | 0.2043 (2) | 0.020* | |
C4B | 0.6025 (4) | 0.5595 (3) | 0.13970 (13) | 0.0198 (3) | |
H7B | 0.699 (3) | 0.430 (4) | 0.1612 (7) | 0.024* | |
C5B | 0.4294 (6) | 0.4604 (5) | 0.0367 (2) | 0.0367 (5) | |
H8B | 0.338 (5) | 0.578 (4) | 0.0158 (10) | 0.055* | |
H9B | 0.296 (5) | 0.290 (5) | 0.0389 (4) | 0.055* | |
H10B | 0.548 (3) | 0.452 (5) | −0.0085 (13) | 0.055* | |
C6B | 0.8267 (5) | 0.8318 (4) | 0.1368 (2) | 0.0285 (4) | |
H11B | 0.955 (4) | 0.8161 (9) | 0.0950 (17) | 0.043* | |
H12B | 0.926 (4) | 0.898 (3) | 0.2031 (15) | 0.043* | |
H13B | 0.740 (2) | 0.953 (3) | 0.1106 (16) | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0171 (5) | 0.0101 (4) | 0.0253 (6) | 0.0065 (4) | 0.0076 (4) | 0.0054 (4) |
O2A | 0.0145 (5) | 0.0147 (5) | 0.0194 (5) | 0.0085 (4) | 0.0030 (4) | 0.0025 (4) |
N1A | 0.0149 (5) | 0.0092 (5) | 0.0156 (6) | 0.0065 (4) | 0.0051 (4) | 0.0038 (4) |
C1A | 0.0136 (6) | 0.0087 (5) | 0.0140 (6) | 0.0055 (4) | 0.0016 (4) | 0.0025 (4) |
C2A | 0.0126 (6) | 0.0091 (5) | 0.0134 (6) | 0.0048 (4) | 0.0026 (4) | 0.0027 (4) |
C3A | 0.0167 (6) | 0.0107 (5) | 0.0149 (6) | 0.0066 (4) | 0.0025 (5) | 0.0035 (4) |
C4A | 0.0191 (7) | 0.0194 (7) | 0.0153 (6) | 0.0046 (5) | 0.0000 (5) | 0.0010 (5) |
C5A | 0.0197 (7) | 0.0230 (7) | 0.0226 (8) | 0.0060 (6) | 0.0090 (6) | 0.0078 (6) |
C6A | 0.0406 (12) | 0.0379 (11) | 0.0188 (8) | 0.0037 (9) | 0.0119 (8) | 0.0088 (7) |
O1B | 0.0176 (5) | 0.0103 (5) | 0.0249 (6) | 0.0065 (4) | 0.0078 (4) | 0.0067 (4) |
O2B | 0.0146 (5) | 0.0152 (5) | 0.0204 (6) | 0.0090 (4) | 0.0030 (4) | 0.0035 (4) |
N1B | 0.0159 (6) | 0.0092 (5) | 0.0176 (6) | 0.0066 (4) | 0.0042 (4) | 0.0038 (4) |
C1B | 0.0134 (6) | 0.0098 (5) | 0.0116 (6) | 0.0057 (4) | 0.0010 (4) | 0.0017 (4) |
C2B | 0.0118 (5) | 0.0092 (5) | 0.0136 (6) | 0.0054 (4) | 0.0031 (4) | 0.0028 (4) |
C3B | 0.0180 (7) | 0.0175 (6) | 0.0152 (6) | 0.0080 (5) | 0.0024 (5) | 0.0058 (5) |
C4B | 0.0282 (8) | 0.0207 (7) | 0.0140 (6) | 0.0116 (6) | 0.0068 (5) | 0.0044 (5) |
C5B | 0.0500 (14) | 0.0376 (11) | 0.0154 (8) | 0.0082 (10) | 0.0030 (8) | −0.0020 (7) |
C6B | 0.0269 (8) | 0.0311 (9) | 0.0266 (9) | 0.0065 (7) | 0.0101 (7) | 0.0107 (7) |
Geometric parameters (Å, º) top
O1A—C1A | 1.255 (2) | O1B—C1B | 1.262 (2) |
O2A—C1A | 1.262 (2) | O2B—C1B | 1.258 (2) |
N1A—C2A | 1.496 (2) | N1B—C2B | 1.492 (2) |
N1A—H1A | 0.93 (3) | N1B—H1B | 0.95 (3) |
N1A—H2A | 0.96 (4) | N1B—H2B | 0.81 (3) |
N1A—H3A | 0.97 (4) | N1B—H3B | 0.92 (3) |
C1A—C2A | 1.539 (2) | C1B—C2B | 1.538 (2) |
C2A—C3A | 1.542 (2) | C2B—C3B | 1.538 (2) |
C2A—H4A | 0.98 (3) | C2B—H4B | 0.91 (3) |
C3A—C4A | 1.534 (2) | C3B—C4B | 1.528 (3) |
C3A—C5A | 1.536 (2) | C3B—H5B | 0.97 (2) |
C3A—H5A | 1.06 (3) | C3B—H6B | 0.97 (2) |
C4A—H6A | 0.96 (2) | C4B—C5B | 1.527 (3) |
C4A—H7A | 0.96 (2) | C4B—C6B | 1.532 (3) |
C4A—H8A | 0.96 (2) | C4B—H7B | 1.02 (3) |
C5A—C6A | 1.521 (3) | C5B—H8B | 0.95 (2) |
C5A—H9A | 0.97 (2) | C5B—H9B | 0.95 (2) |
C5A—H10A | 0.97 (2) | C5B—H10B | 0.95 (2) |
C6A—H11A | 0.94 (2) | C6B—H11B | 0.97 (2) |
C6A—H12A | 0.94 (2) | C6B—H12B | 0.97 (2) |
C6A—H13A | 0.94 (2) | C6B—H13B | 0.97 (2) |
| | | |
C2A—N1A—H1A | 111.5 (18) | C2B—N1B—H1B | 110.9 (19) |
C2A—N1A—H2A | 112 (2) | C2B—N1B—H2B | 107 (2) |
H1A—N1A—H2A | 106 (3) | H1B—N1B—H2B | 109 (3) |
C2A—N1A—H3A | 112 (3) | C2B—N1B—H3B | 106.9 (19) |
H1A—N1A—H3A | 106 (3) | H1B—N1B—H3B | 113 (3) |
H2A—N1A—H3A | 110 (3) | H2B—N1B—H3B | 110 (3) |
O1A—C1A—O2A | 125.61 (15) | O2B—C1B—O1B | 125.76 (15) |
O1A—C1A—C2A | 117.17 (14) | O2B—C1B—C2B | 118.25 (13) |
O2A—C1A—C2A | 117.22 (13) | O1B—C1B—C2B | 115.98 (14) |
N1A—C2A—C1A | 109.06 (12) | N1B—C2B—C1B | 109.08 (12) |
N1A—C2A—C3A | 109.94 (13) | N1B—C2B—C3B | 108.37 (13) |
C1A—C2A—C3A | 113.05 (13) | C1B—C2B—C3B | 110.58 (13) |
N1A—C2A—H4A | 108.22 (8) | N1B—C2B—H4B | 109.60 (8) |
C1A—C2A—H4A | 108.22 (8) | C1B—C2B—H4B | 109.60 (8) |
C3A—C2A—H4A | 108.22 (8) | C3B—C2B—H4B | 109.60 (8) |
C4A—C3A—C5A | 111.35 (14) | C4B—C3B—C2B | 114.99 (14) |
C4A—C3A—C2A | 112.08 (12) | C4B—C3B—H5B | 108.52 (9) |
C5A—C3A—C2A | 110.50 (14) | C2B—C3B—H5B | 108.52 (8) |
C4A—C3A—H5A | 107.56 (9) | C4B—C3B—H6B | 108.52 (9) |
C5A—C3A—H5A | 107.56 (9) | C2B—C3B—H6B | 108.52 (9) |
C2A—C3A—H5A | 107.56 (9) | H5B—C3B—H6B | 107.5 |
C3A—C4A—H6A | 109.47 (10) | C5B—C4B—C3B | 109.7 (2) |
C3A—C4A—H7A | 109.47 (9) | C5B—C4B—C6B | 110.2 (2) |
H6A—C4A—H7A | 109.5 | C3B—C4B—C6B | 111.5 (2) |
C3A—C4A—H8A | 109.47 (8) | C5B—C4B—H7B | 108.46 (13) |
H6A—C4A—H8A | 109.5 | C3B—C4B—H7B | 108.46 (9) |
H7A—C4A—H8A | 109.5 | C6B—C4B—H7B | 108.46 (11) |
C6A—C5A—C3A | 113.2 (2) | C4B—C5B—H8B | 109.47 (13) |
C6A—C5A—H9A | 108.93 (14) | C4B—C5B—H9B | 109.47 (11) |
C3A—C5A—H9A | 108.93 (9) | H8B—C5B—H9B | 109.5 |
C6A—C5A—H10A | 108.93 (12) | C4B—C5B—H10B | 109.47 (13) |
C3A—C5A—H10A | 108.93 (9) | H8B—C5B—H10B | 109.5 |
H9A—C5A—H10A | 107.7 | H9B—C5B—H10B | 109.5 |
C5A—C6A—H11A | 109.47 (14) | C4B—C6B—H11B | 109.47 (11) |
C5A—C6A—H12A | 109.47 (12) | C4B—C6B—H12B | 109.47 (10) |
H11A—C6A—H12A | 109.5 | H11B—C6B—H12B | 109.5 |
C5A—C6A—H13A | 109.47 (12) | C4B—C6B—H13B | 109.47 (11) |
H11A—C6A—H13A | 109.5 | H11B—C6B—H13B | 109.5 |
H12A—C6A—H13A | 109.5 | H12B—C6B—H13B | 109.5 |
| | | |
O1A—C1A—C2A—N1A | −23.9 (2) | C2A—C3A—C5A—C6A | 169.9 (2) |
O2A—C1A—C2A—N1A | 156.94 (14) | O2B—C1B—C2B—N1B | −147.82 (14) |
O1A—C1A—C2A—C3A | 98.7 (2) | O1B—C1B—C2B—N1B | 33.0 (2) |
O2A—C1A—C2A—C3A | −80.4 (2) | O2B—C1B—C2B—C3B | 93.1 (2) |
N1A—C2A—C3A—C4A | 81.6 (2) | O1B—C1B—C2B—C3B | −86.1 (2) |
C1A—C2A—C3A—C4A | −40.5 (2) | N1B—C2B—C3B—C4B | 169.01 (13) |
N1A—C2A—C3A—C5A | −153.54 (13) | C1B—C2B—C3B—C4B | −71.5 (2) |
C1A—C2A—C3A—C5A | 84.3 (2) | C2B—C3B—C4B—C5B | 161.1 (2) |
C4A—C3A—C5A—C6A | −64.8 (2) | C2B—C3B—C4B—C6B | −76.5 (2) |