Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010001502X/qa0435sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010001502X/qa0435Isup2.hkl |
CCDC reference: 156209
Z-Pro-Leuol was synthezized from commercially available Z—L-Pro-OH (from Bachem, Bubendorf, Switzerland) and H—L-Leuol (from Fluka, Buchs, Switzerland) by using WSC (water-soluble carbodiimide) and HOBt (1-hydroxybezotrialole) as coupling reagents. This approach is known to prevent racemization. Further, it is known that C-terminal Pro in peptide coupling does not racemize as no azlactone can be formed on activation. Chiral purity was also confirmed by enantioselective gas chromatography of a total hydrolysate of the dipeptide on a Chirasil-L-Val capillary column according to procedures described previously (Brückner & Jung, 1982). For this reason, the Flack parameter was not refined. The protected dipeptide was crystallized from a hot ethanol–water mixture (60:40). Very few plate-like crystals were obtained and all reached a length of 1 mm. The crystals were fragile and easily damaged by attempts to cut smaller pieces with more appopriate dimensions for data collection. An intact crystal was sealed in a glass capillary for data collection. The collimator used has a diameter of 1 mm.
Data were collected from θ = 1–70°. Subsequently, 1978 Friedel pairs were measured, from θ = 1–49°. All equivalent data were averaged, including the Friedel pairs. H atoms were calculated and a riding model was used during the refinement. The C-terminal H atom was located by difference Fourier syntheses and its displacement parameter was fixed during refinement.
Data collection: CAD-4 Software (Enraf Nonius, 1989); cell refinement: CAD-4 Software; data reduction: Xtal3.7 DIFDAT ABSORB ADDREF (Hall et al., 2000); program(s) used to solve structure: Xtal3.7 CRISP; program(s) used to refine structure: Xtal3.7 CRILSQ; software used to prepare material for publication: Xtal3.7 BONDLA CIFIO.
C19H28N2O4 | F(000) = 752 |
Mr = 348.44 | Dx = 1.200 Mg m−3 |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 6.371 (4) Å | θ = 10.0–21.4° |
b = 8.824 (8) Å | µ = 0.68 mm−1 |
c = 34.303 (10) Å | T = 293 K |
V = 1928 (2) Å3 | Rod, colourless |
Z = 4 | 1.0 × 0.4 × 0.2 mm |
CAD-4 diffractometer | Rint = 0.069 |
ω–4/3θ scans | θmax = 70.0°, θmin = 2.6° |
Absorption correction: analytical (Xtal3.7 ABSORB; Hall et al., 2000) | h = −6→7 |
Tmin = 0.736, Tmax = 0.875 | k = −8→10 |
4821 measured reflections | l = −33→41 |
2111 independent reflections | 5 standard reflections every 3600 min |
1398 reflections with I > 2.5σ(I) | intensity decay: 11.2% |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | Weighting scheme based on measured s.u.'s w = 1/σ2(F) |
R[F2 > 2σ(F2)] = 0.067 | (Δ/σ)max < 0.001 |
wR(F2) = 0.093 | Δρmax = 0.39 e Å−3 |
S = 2.00 | Δρmin = −0.49 e Å−3 |
2049 reflections | Extinction correction: Zachariasen (1967) |
227 parameters | Extinction coefficient: 4647.9 (18) |
0 restraints | Absolute structure: assumed from synthesis, see text |
4 constraints |
C19H28N2O4 | V = 1928 (2) Å3 |
Mr = 348.44 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 6.371 (4) Å | µ = 0.68 mm−1 |
b = 8.824 (8) Å | T = 293 K |
c = 34.303 (10) Å | 1.0 × 0.4 × 0.2 mm |
CAD-4 diffractometer | 1398 reflections with I > 2.5σ(I) |
Absorption correction: analytical (Xtal3.7 ABSORB; Hall et al., 2000) | Rint = 0.069 |
Tmin = 0.736, Tmax = 0.875 | 5 standard reflections every 3600 min |
4821 measured reflections | intensity decay: 11.2% |
2111 independent reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 2.00 | Δρmax = 0.39 e Å−3 |
2049 reflections | Δρmin = −0.49 e Å−3 |
227 parameters | Absolute structure: assumed from synthesis, see text |
x | y | z | Uiso*/Ueq | ||
C06 | 1.0761 (10) | 0.2037 (6) | 0.60525 (14) | 0.063 (4) | |
C01 | 0.8772 (10) | 0.2614 (9) | 0.60357 (19) | 0.095 (5) | |
C02 | 0.7568 (14) | 0.2391 (10) | 0.5708 (2) | 0.120 (6) | |
C03 | 0.8200 (17) | 0.1584 (10) | 0.5413 (2) | 0.122 (7) | |
C04 | 1.025 (2) | 0.0998 (11) | 0.5420 (2) | 0.143 (8) | |
C05 | 1.1444 (12) | 0.1223 (8) | 0.5732 (2) | 0.100 (5) | |
C07 | 1.2225 (10) | 0.2249 (6) | 0.63978 (15) | 0.074 (4) | |
O01 | 1.1434 (5) | 0.3468 (4) | 0.66349 (8) | 0.056 (2) | |
C08 | 1.2873 (8) | 0.4045 (6) | 0.68994 (15) | 0.054 (3) | |
O08 | 1.4696 (5) | 0.3631 (4) | 0.68987 (10) | 0.065 (2) | |
N1 | 1.1986 (6) | 0.5048 (4) | 0.71294 (11) | 0.050 (2) | |
C1A | 0.9774 (7) | 0.5514 (6) | 0.71189 (12) | 0.048 (3) | |
C1B | 0.9482 (10) | 0.6420 (7) | 0.74971 (13) | 0.075 (4) | |
C1G | 1.1330 (11) | 0.6045 (9) | 0.77379 (17) | 0.099 (5) | |
C1D | 1.3109 (8) | 0.5663 (6) | 0.74663 (15) | 0.063 (3) | |
C1 | 0.9286 (7) | 0.6456 (6) | 0.67665 (12) | 0.048 (3) | |
O1 | 1.0475 (5) | 0.7454 (4) | 0.66423 (10) | 0.069 (2) | |
N2 | 0.7349 (6) | 0.6280 (5) | 0.66153 (11) | 0.053 (2) | |
C2A | 0.6460 (8) | 0.7218 (6) | 0.63108 (13) | 0.052 (3) | |
C2B | 0.4690 (8) | 0.6316 (6) | 0.61111 (12) | 0.056 (3) | |
C2G | 0.3603 (10) | 0.7060 (7) | 0.57690 (14) | 0.071 (4) | |
C2D1 | 0.1933 (11) | 0.6045 (8) | 0.56176 (19) | 0.102 (5) | |
C2D2 | 0.5115 (15) | 0.7432 (12) | 0.54529 (18) | 0.135 (7) | |
C2 | 0.5742 (7) | 0.8717 (6) | 0.64861 (14) | 0.059 (3) | |
O2 | 0.4373 (6) | 0.8583 (4) | 0.68042 (10) | 0.075 (2) | |
H01 | 0.82220 | 0.31678 | 0.62500 | 0.11800* | |
H02 | 0.62172 | 0.28451 | 0.56965 | 0.15000* | |
H03 | 0.72961 | 0.13951 | 0.51979 | 0.15300* | |
H04 | 1.07794 | 0.04463 | 0.52031 | 0.17900* | |
H05 | 1.28202 | 0.08090 | 0.57358 | 0.12500* | |
H07a | 1.22772 | 0.13425 | 0.65469 | 0.09300* | |
H07b | 1.35943 | 0.24915 | 0.63076 | 0.09300* | |
H1A | 0.88963 | 0.46435 | 0.71228 | 0.06000* | |
H1Ba | 0.94377 | 0.74759 | 0.74437 | 0.09400* | |
H1Bb | 0.82256 | 0.61250 | 0.76256 | 0.09400* | |
H1Ga | 1.17006 | 0.68901 | 0.78952 | 0.12300* | |
H1Gb | 1.10254 | 0.52011 | 0.79002 | 0.12300* | |
H1Da | 1.40212 | 0.49298 | 0.75777 | 0.07800* | |
H1Db | 1.38907 | 0.65404 | 0.73981 | 0.07800* | |
H2A | 0.75218 | 0.74202 | 0.61234 | 0.06400* | |
H2Ba | 0.52757 | 0.53895 | 0.60211 | 0.07000* | |
H2Bb | 0.36517 | 0.61092 | 0.63027 | 0.07000* | |
H2G | 0.29698 | 0.79729 | 0.58565 | 0.08800* | |
H2D1a | 0.12550 | 0.65166 | 0.54029 | 0.15300* | |
H2D1b | 0.09363 | 0.58547 | 0.58177 | 0.15300* | |
H2D1c | 0.25398 | 0.51150 | 0.55355 | 0.15300* | |
H2D2a | 0.43888 | 0.78970 | 0.52427 | 0.20200* | |
H2D2b | 0.57722 | 0.65295 | 0.53642 | 0.20200* | |
H2D2c | 0.61510 | 0.81088 | 0.55500 | 0.20200* | |
H2c | 0.69512 | 0.92556 | 0.65700 | 0.07400* | |
H2b | 0.50477 | 0.92783 | 0.62880 | 0.07400* | |
H2 | 0.65314 | 0.55089 | 0.67128 | 0.06600* | |
H | 0.3073 (6) | 0.8793 (4) | 0.67241 (10) | 0.20000* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C06 | 0.068 (4) | 0.051 (3) | 0.070 (3) | 0.008 (3) | 0.005 (3) | −0.002 (3) |
C01 | 0.061 (4) | 0.119 (6) | 0.105 (5) | 0.017 (4) | −0.002 (4) | −0.035 (4) |
C02 | 0.116 (7) | 0.136 (7) | 0.109 (5) | 0.022 (5) | −0.031 (6) | −0.048 (6) |
C03 | 0.148 (8) | 0.107 (7) | 0.112 (6) | 0.036 (6) | −0.043 (6) | −0.028 (5) |
C04 | 0.203 (11) | 0.128 (8) | 0.098 (5) | 0.047 (8) | −0.036 (7) | −0.059 (5) |
C05 | 0.100 (5) | 0.096 (5) | 0.103 (5) | 0.016 (5) | 0.004 (5) | −0.036 (4) |
C07 | 0.076 (4) | 0.064 (4) | 0.083 (4) | 0.005 (3) | −0.001 (3) | −0.015 (3) |
O01 | 0.0399 (18) | 0.057 (2) | 0.070 (2) | 0.0076 (17) | −0.0028 (16) | −0.0090 (17) |
C08 | 0.049 (3) | 0.042 (3) | 0.070 (3) | 0.003 (3) | 0.001 (3) | 0.014 (3) |
O08 | 0.0301 (18) | 0.058 (2) | 0.107 (3) | 0.0137 (16) | −0.0007 (17) | 0.008 (2) |
N1 | 0.037 (2) | 0.050 (2) | 0.065 (3) | 0.0124 (19) | −0.014 (2) | −0.002 (2) |
C1A | 0.030 (2) | 0.054 (3) | 0.060 (3) | 0.007 (2) | −0.002 (2) | −0.001 (3) |
C1B | 0.074 (4) | 0.098 (4) | 0.052 (3) | 0.003 (4) | −0.012 (3) | 0.004 (3) |
C1G | 0.076 (4) | 0.126 (6) | 0.095 (4) | 0.033 (4) | −0.025 (4) | −0.044 (4) |
C1D | 0.046 (3) | 0.062 (3) | 0.081 (3) | −0.003 (3) | −0.021 (3) | 0.004 (3) |
C1 | 0.032 (2) | 0.056 (3) | 0.055 (3) | 0.008 (2) | −0.007 (2) | −0.007 (2) |
O1 | 0.0361 (19) | 0.070 (3) | 0.101 (3) | −0.0110 (18) | −0.002 (2) | 0.020 (2) |
N2 | 0.038 (2) | 0.056 (3) | 0.065 (2) | −0.0001 (19) | −0.0093 (18) | 0.008 (2) |
C2A | 0.040 (3) | 0.056 (3) | 0.059 (3) | 0.002 (2) | −0.007 (2) | 0.009 (3) |
C2B | 0.050 (3) | 0.056 (3) | 0.062 (3) | 0.006 (3) | −0.010 (3) | −0.006 (3) |
C2G | 0.073 (4) | 0.078 (4) | 0.061 (3) | 0.001 (3) | −0.015 (3) | 0.002 (3) |
C2D1 | 0.094 (5) | 0.116 (6) | 0.095 (4) | −0.003 (5) | −0.039 (4) | 0.004 (4) |
C2D2 | 0.135 (8) | 0.205 (9) | 0.064 (3) | −0.031 (6) | −0.014 (5) | 0.037 (4) |
C2 | 0.033 (3) | 0.060 (3) | 0.085 (3) | 0.004 (3) | −0.009 (3) | 0.004 (3) |
O2 | 0.058 (2) | 0.080 (3) | 0.086 (2) | −0.001 (2) | −0.002 (2) | −0.021 (2) |
C06—C01 | 1.367 (9) | C1G—H1Ga | 0.950 (7) |
C06—C05 | 1.382 (9) | C1G—H1Gb | 0.950 (7) |
C06—C07 | 1.519 (8) | C1D—H1Da | 0.950 (5) |
C01—C02 | 1.375 (10) | C1D—H1Db | 0.950 (5) |
C01—H01 | 0.950 (7) | C1—O1 | 1.237 (6) |
C02—C03 | 1.302 (12) | C1—N2 | 1.347 (6) |
C02—H02 | 0.950 (9) | N2—C2A | 1.448 (6) |
C03—C04 | 1.405 (16) | N2—H2 | 0.920 (4) |
C03—H03 | 0.950 (9) | C2A—C2B | 1.541 (7) |
C04—C05 | 1.329 (12) | C2A—C2 | 1.523 (7) |
C04—H04 | 0.950 (9) | C2A—H2A | 0.950 (5) |
C05—H05 | 0.950 (8) | C2B—C2G | 1.512 (7) |
C07—O01 | 1.440 (6) | C2B—H2Ba | 0.950 (5) |
C07—H07a | 0.950 (5) | C2B—H2Bb | 0.950 (5) |
C07—H07b | 0.950 (6) | C2G—C2D1 | 1.484 (9) |
O01—C08 | 1.386 (6) | C2G—C2D2 | 1.487 (10) |
C08—O08 | 1.218 (6) | C2G—H2G | 0.950 (6) |
C08—N1 | 1.313 (6) | C2D1—H2D1a | 0.950 (7) |
N1—C1A | 1.469 (6) | C2D1—H2D1b | 0.950 (7) |
N1—C1D | 1.464 (6) | C2D1—H2D1c | 0.950 (7) |
C1A—C1B | 1.535 (7) | C2D2—H2D2a | 0.950 (8) |
C1A—C1 | 1.499 (6) | C2D2—H2D2b | 0.950 (10) |
C1A—H1A | 0.950 (5) | C2D2—H2D2c | 0.950 (9) |
C1B—C1G | 1.476 (9) | C2—O2 | 1.402 (6) |
C1B—H1Ba | 0.950 (6) | C2—H2c | 0.950 (5) |
C1B—H1Bb | 0.950 (6) | C2—H2b | 0.950 (5) |
C1G—C1D | 1.505 (8) | O2—H | 0.892 (5) |
C06···C02 | 2.373 (10) | C1D···H2Bb | 4.026 (5) |
C06···C03 | 2.763 (11) | C1D···H2c | 3.532 (5) |
C06···C04 | 2.379 (9) | C1D···H2 | 3.384 (5) |
C06···O01 | 2.402 (6) | C1D···H | 3.757 (7) |
C06···C08 | 3.659 (7) | C1···C2A | 2.477 (7) |
C06···O08 | 4.085 (6) | C1···C2B | 3.694 (7) |
C06···C2D1 | 3.911 (9) | C1···C2B | 4.114 (7) |
C06···H01 | 2.018 (6) | C1···C2G | 4.423 (7) |
C06···H02 | 3.222 (6) | C1···C2D1 | 4.302 (8) |
C06···H02 | 3.753 (6) | C1···C2 | 3.163 (7) |
C06···H03 | 3.713 (5) | C1···O2 | 3.652 (6) |
C06···H04 | 3.234 (5) | C1···O2 | 3.748 (6) |
C06···H05 | 2.019 (6) | C1···H01 | 3.466 (5) |
C06···H07a | 2.046 (5) | C1···H1A | 2.028 (5) |
C06···H07b | 2.046 (6) | C1···H1Ba | 2.493 (4) |
C06···H1Ga | 3.938 (5) | C1···H1Bb | 3.037 (4) |
C06···H2G | 3.910 (6) | C1···H1Gb | 3.503 (6) |
C06···H2D1b | 3.466 (6) | C1···H1Db | 3.648 (5) |
C06···H2D1c | 3.436 (6) | C1···H2A | 2.618 (4) |
C06···H2c | 3.881 (6) | C1···H2Ba | 3.735 (5) |
C06···H2b | 3.746 (6) | C1···H2Bb | 3.938 (5) |
C06···H | 3.958 (7) | C1···H2Bb | 3.219 (5) |
C01···C03 | 2.350 (11) | C1···H2D1b | 3.461 (4) |
C01···C04 | 2.718 (11) | C1···H2c | 2.962 (5) |
C01···C05 | 2.342 (10) | C1···H2b | 4.023 (5) |
C01···C07 | 4.363 (9) | C1···H2 | 1.952 (5) |
C01···C07 | 2.547 (9) | C1···H | 3.178 (6) |
C01···O01 | 2.769 (7) | O1···N2 | 2.246 (5) |
C01···C08 | 4.147 (8) | O1···C2A | 2.807 (6) |
C01···O08 | 4.039 (7) | O1···C2A | 3.985 (6) |
C01···C1G | 4.429 (9) | O1···C2B | 4.232 (6) |
C01···C1 | 4.229 (9) | O1···C2B | 3.397 (6) |
C01···N2 | 3.904 (9) | O1···C2G | 3.615 (6) |
C01···C2A | 4.423 (10) | O1···C2D1 | 3.842 (8) |
C01···C2B | 4.183 (9) | O1···C2 | 3.576 (6) |
C01···C2D1 | 3.909 (10) | O1···C2 | 3.259 (6) |
C01···C2 | 4.235 (9) | O1···O2 | 4.051 (6) |
C01···H02 | 2.011 (6) | O1···H | 2.053 (5) |
C01···H03 | 3.209 (7) | O1···O2 | 2.733 (5) |
C01···H04 | 3.668 (7) | O1···H07a | 3.633 (5) |
C01···H05 | 3.201 (7) | O1···H1A | 3.143 (4) |
C01···H07a | 3.053 (7) | O1···H1Ba | 2.827 (4) |
C01···H07b | 3.213 (7) | O1···H1Bb | 3.848 (4) |
C01···H07b | 3.429 (7) | O1···H1Gb | 3.042 (4) |
C01···H1Ga | 3.735 (7) | O1···H1Db | 3.479 (4) |
C01···H2Ba | 3.311 (7) | O1···H2A | 2.590 (4) |
C01···H2D1b | 3.262 (8) | O1···H2Bb | 2.619 (4) |
C01···H2D1c | 3.685 (7) | O1···H2G | 3.163 (4) |
C01···H2c | 3.672 (8) | O1···H2D1b | 3.175 (4) |
C01···H2b | 3.878 (7) | O1···H2c | 2.762 (4) |
C01···H2 | 3.736 (7) | O1···H2b | 3.544 (4) |
C02···C04 | 2.326 (14) | O1···H2b | 4.003 (4) |
C02···C04 | 4.378 (12) | O1···H2 | 3.052 (4) |
C02···C05 | 2.677 (12) | O1···H | 2.053 (5) |
C02···C05 | 4.036 (12) | N2···C2B | 2.421 (6) |
C02···C07 | 4.147 (10) | N2···C2G | 3.820 (7) |
C02···C07 | 3.797 (10) | N2···C2D2 | 4.354 (8) |
C02···O01 | 4.133 (9) | N2···C2 | 2.422 (6) |
C02···C2B | 4.156 (10) | N2···O2 | 2.854 (6) |
C02···C2D1 | 4.270 (12) | N2···H01 | 3.070 (5) |
C02···C2 | 4.358 (10) | N2···H1A | 2.468 (4) |
C02···H01 | 2.025 (8) | N2···H1Ba | 3.310 (4) |
C02···H03 | 1.966 (8) | N2···H1Bb | 3.513 (4) |
C02···H04 | 3.183 (9) | N2···H1Gb | 3.975 (5) |
C02···H04 | 3.835 (8) | N2···H1Db | 3.481 (4) |
C02···H05 | 3.332 (9) | N2···H2A | 1.967 (4) |
C02···H05 | 3.627 (9) | N2···H2Ba | 2.553 (4) |
C02···H07b | 3.263 (8) | N2···H2Bb | 2.592 (4) |
C02···H2Ba | 3.207 (9) | N2···H2D1b | 3.585 (4) |
C02···H2D1b | 3.754 (9) | N2···H2c | 2.642 (5) |
C02···H2D1c | 4.020 (9) | N2···H2b | 3.226 (4) |
C02···H2D2b | 4.005 (9) | N2···H | 3.532 (6) |
C02···H2D2c | 3.922 (10) | C2A···C2G | 2.605 (7) |
C02···H2b | 3.752 (9) | C2A···C2D1 | 4.345 (9) |
C03···C04 | 4.030 (13) | C2A···C2D1 | 3.878 (9) |
C03···C05 | 2.361 (13) | C2A···C2D2 | 3.071 (8) |
C03···C07 | 4.282 (11) | C2A···O2 | 2.467 (6) |
C03···C2D1 | 4.304 (11) | C2A···H01 | 3.752 (6) |
C03···C2D2 | 4.159 (14) | C2A···H1A | 3.915 (5) |
C03···H01 | 3.194 (8) | C2A···H2Ba | 2.039 (5) |
C03···H02 | 1.944 (10) | C2A···H2Bb | 2.039 (5) |
C03···H03 | 3.792 (10) | C2A···H2G | 2.796 (5) |
C03···H04 | 2.056 (10) | C2A···H2D1b | 3.527 (5) |
C03···H04 | 3.703 (9) | C2A···H2D2a | 3.940 (5) |
C03···H05 | 3.219 (10) | C2A···H2D2b | 3.332 (5) |
C03···H05 | 3.666 (10) | C2A···H2D2c | 2.733 (5) |
C03···H2D1c | 3.607 (9) | C2A···H2c | 2.030 (5) |
C03···H2D2c | 3.366 (10) | C2A···H2b | 2.030 (5) |
C04···C07 | 3.749 (10) | C2A···H2 | 2.044 (5) |
C04···C2G | 4.251 (12) | C2A···H | 2.933 (6) |
C04···C2D2 | 4.258 (12) | C2B···C2D1 | 2.451 (8) |
C04···C2D2 | 4.418 (15) | C2B···C2D2 | 2.478 (8) |
C04···H01 | 3.667 (9) | C2B···C2 | 2.568 (7) |
C04···H02 | 3.188 (12) | C2B···O2 | 3.114 (6) |
C04···H02 | 4.010 (8) | C2B···H01 | 3.607 (5) |
C04···H03 | 3.388 (10) | C2B···H02 | 3.514 (5) |
C04···H03 | 2.060 (12) | C2B···H07b | 3.511 (6) |
C04···H05 | 1.971 (12) | C2B···H2A | 2.051 (5) |
C04···H07b | 3.943 (10) | C2B···H2G | 2.025 (5) |
C04···H2G | 3.517 (10) | C2B···H2D1a | 3.274 (5) |
C04···H2D1a | 4.006 (10) | C2B···H2D1b | 2.626 (5) |
C04···H2D1c | 3.832 (9) | C2B···H2D1c | 2.626 (5) |
C04···H2D1c | 3.935 (11) | C2B···H2D2a | 3.295 (4) |
C04···H2D2a | 3.848 (11) | C2B···H2D2b | 2.660 (4) |
C04···H2D2b | 3.509 (9) | C2B···H2D2c | 2.660 (5) |
C04···H2D2c | 3.677 (12) | C2B···H2c | 3.359 (5) |
C05···C07 | 2.506 (9) | C2B···H2b | 2.693 (5) |
C05···O01 | 3.676 (8) | C2B···H2 | 2.479 (4) |
C05···C2G | 3.925 (10) | C2B···H | 3.204 (6) |
C05···C2D1 | 4.284 (11) | C2G···C2 | 3.170 (7) |
C05···C2D2 | 4.193 (12) | C2G···O2 | 3.829 (6) |
C05···C2 | 4.368 (9) | C2G···H04 | 3.992 (6) |
C05···H01 | 3.211 (7) | C2G···H05 | 3.348 (7) |
C05···H02 | 3.626 (8) | C2G···H2A | 2.795 (6) |
C05···H02 | 3.363 (8) | C2G···H2Ba | 2.014 (6) |
C05···H03 | 3.220 (7) | C2G···H2Bb | 2.014 (5) |
C05···H03 | 3.859 (7) | C2G···H2D1a | 2.011 (6) |
C05···H04 | 1.986 (7) | C2G···H2D1b | 2.011 (6) |
C05···H07a | 2.846 (7) | C2G···H2D1c | 2.011 (6) |
C05···H07b | 2.650 (7) | C2G···H2D2a | 2.014 (5) |
C05···H2G | 3.058 (7) | C2G···H2D2b | 2.014 (6) |
C05···H2D1c | 3.569 (8) | C2G···H2D2c | 2.014 (6) |
C05···H2D2a | 3.867 (7) | C2G···H2c | 3.982 (6) |
C05···H2b | 3.442 (7) | C2G···H2b | 2.802 (6) |
C07···C08 | 2.375 (7) | C2G···H2 | 3.979 (5) |
C07···O08 | 2.630 (7) | C2G···H | 3.632 (6) |
C07···N1 | 3.524 (7) | C2D1···C2D2 | 2.435 (12) |
C07···C1A | 4.106 (7) | C2D1···C2D2 | 4.078 (10) |
C07···C1B | 4.011 (7) | C2D1···H02 | 3.936 (8) |
C07···C1G | 3.879 (9) | C2D1···H03 | 3.538 (7) |
C07···C1 | 4.346 (8) | C2D1···H04 | 3.957 (7) |
C07···C2B | 4.039 (8) | C2D1···H2A | 3.519 (7) |
C07···C2D1 | 4.292 (9) | C2D1···H2Ba | 2.605 (7) |
C07···C2 | 3.851 (8) | C2D1···H2Bb | 2.593 (7) |
C07···O2 | 3.779 (7) | C2D1···H2G | 2.000 (7) |
C07···H01 | 3.938 (7) | C2D1···H2D2a | 2.602 (7) |
C07···H01 | 2.724 (6) | C2D1···H2D2a | 3.494 (7) |
C07···H02 | 3.540 (6) | C2D1···H2D2b | 2.630 (7) |
C07···H05 | 2.630 (5) | C2D1···H2D2c | 3.254 (8) |
C07···H1A | 3.892 (6) | C2D2···C2 | 3.742 (8) |
C07···H1Bb | 3.506 (5) | C2D2···H03 | 3.863 (10) |
C07···H1Ga | 3.498 (6) | C2D2···H04 | 3.420 (9) |
C07···H1Gb | 3.654 (6) | C2D2···H04 | 3.929 (10) |
C07···H2Ba | 3.623 (6) | C2D2···H05 | 3.458 (10) |
C07···H2Bb | 3.541 (6) | C2D2···H2A | 2.764 (7) |
C07···H2D1b | 3.842 (6) | C2D2···H2Ba | 2.657 (8) |
C07···H2D1c | 3.897 (6) | C2D2···H2Bb | 3.276 (7) |
C07···H2b | 3.201 (6) | C2D2···H2G | 2.003 (8) |
C07···H | 3.293 (7) | C2D2···H2D1a | 3.163 (7) |
O01···O08 | 2.271 (5) | C2D2···H2D1a | 2.594 (10) |
O01···N1 | 2.223 (5) | C2D2···H2D1a | 3.998 (10) |
O01···C1A | 2.671 (6) | C2D2···H2D1b | 3.255 (9) |
O01···C1B | 3.532 (6) | C2D2···H2D1c | 2.637 (10) |
O01···C1B | 4.133 (6) | C2D2···H2D2a | 3.632 (8) |
O01···C1G | 3.507 (8) | C2D2···H2b | 3.296 (7) |
O01···C1D | 3.609 (6) | C2···H05 | 3.674 (5) |
O01···C1 | 3.004 (6) | C2···H07a | 3.207 (5) |
O01···O1 | 3.570 (6) | C2···H07b | 3.653 (6) |
O01···N2 | 3.597 (5) | C2···H1Ga | 3.873 (5) |
O01···C2B | 3.721 (6) | C2···H1Gb | 3.223 (5) |
O01···C2D1 | 4.177 (8) | C2···H1Da | 3.388 (5) |
O01···H01 | 2.450 (3) | C2···H1Db | 3.856 (5) |
O01···H05 | 3.975 (3) | C2···H2A | 2.035 (5) |
O01···H07a | 1.974 (4) | C2···H2Ba | 3.355 (5) |
O01···H07b | 1.974 (3) | C2···H2Bb | 2.732 (5) |
O01···H1A | 2.548 (3) | C2···H2G | 2.866 (5) |
O01···H1Ba | 3.326 (3) | C2···H2D2c | 3.266 (5) |
O01···H1Bb | 3.280 (3) | C2···H2 | 2.978 (5) |
O01···H1Ga | 2.920 (3) | C2···H | 1.887 (6) |
O01···H1Gb | 3.648 (4) | O2···H07a | 2.914 (4) |
O01···H1Da | 3.852 (3) | O2···H07b | 3.878 (5) |
O01···H2Ba | 3.647 (3) | O2···H1Ba | 3.956 (4) |
O01···H2Bb | 2.954 (4) | O2···H1Bb | 3.405 (4) |
O01···H2D1b | 3.520 (3) | O2···H1Ga | 3.979 (4) |
O01···H2 | 3.615 (4) | O2···H1Gb | 3.415 (4) |
O01···H2 | 3.723 (4) | O2···H1Gb | 3.859 (4) |
C08···C1A | 2.479 (7) | O2···H1Da | 2.637 (4) |
C08···C1B | 3.449 (8) | O2···H1Db | 2.738 (4) |
C08···C1B | 3.642 (8) | O2···H1Db | 3.940 (4) |
C08···C1G | 3.965 (9) | O2···H2A | 3.245 (4) |
C08···C1G | 3.515 (8) | O2···H2Ba | 3.936 (4) |
C08···C1D | 2.417 (7) | O2···H2Bb | 2.817 (4) |
C08···C1 | 3.155 (7) | O2···H2G | 3.414 (4) |
C08···O1 | 3.487 (6) | O2···H2c | 1.922 (4) |
C08···N2 | 3.602 (6) | O2···H2b | 1.923 (4) |
C08···N2 | 4.150 (7) | O2···H2 | 3.058 (4) |
C08···C2A | 4.140 (7) | H01···H02 | 2.3059 (7) |
C08···C2B | 3.559 (7) | H01···H07a | 3.2104 (15) |
C08···O2 | 4.131 (7) | H01···H07b | 3.480 (2) |
C08···H01 | 3.787 (5) | H01···H07b | 3.0145 (19) |
C08···H07a | 2.700 (5) | H01···H1A | 3.2930 (9) |
C08···H07b | 2.492 (5) | H01···H1Ga | 3.1419 (9) |
C08···H1A | 3.949 (6) | H01···H2Ba | 2.8254 (15) |
C08···H1A | 2.699 (5) | H01···H2D1b | 3.2880 (17) |
C08···H1Ba | 3.027 (5) | H01···H2 | 2.8192 (15) |
C08···H1Bb | 3.128 (5) | H02···H03 | 2.2438 (8) |
C08···H1Ga | 4.008 (5) | H02···H04 | 3.4457 (10) |
C08···H1Ga | 3.550 (5) | H02···H05 | 2.8160 (15) |
C08···H1Gb | 3.770 (5) | H02···H07b | 2.6989 (8) |
C08···H1Da | 2.561 (5) | H02···H2Ba | 2.5770 (18) |
C08···H1Db | 3.865 (5) | H02···H2D1c | 3.1314 (17) |
C08···H1Db | 2.863 (5) | H02···H2D2b | 3.457 (3) |
C08···H2Ba | 3.582 (5) | H03···H04 | 2.3719 (14) |
C08···H2Bb | 2.785 (5) | H03···H04 | 3.255 (2) |
C08···H2 | 2.741 (5) | H03···H05 | 3.4355 (16) |
O08···N1 | 2.274 (5) | H03···H2D1a | 3.3599 (19) |
O08···C1A | 3.714 (6) | H03···H2D1c | 2.8511 (9) |
O08···C1A | 3.629 (6) | H03···H2D2a | 3.603 (3) |
O08···C1B | 3.897 (7) | H03···H2D2c | 3.225 (2) |
O08···C1G | 4.174 (8) | H04···H05 | 2.2653 (7) |
O08···C1G | 3.629 (8) | H04···H2G | 3.4256 (14) |
O08···C1D | 3.682 (6) | H04···H2D1a | 3.548 (3) |
O08···C1D | 2.833 (6) | H04···H2D1c | 3.3052 (10) |
O08···C1 | 3.869 (6) | H04···H2D2a | 3.439 (2) |
O08···C1 | 4.278 (6) | H04···H2D2a | 3.2197 (18) |
O08···N2 | 3.044 (5) | H04···H2D2b | 2.6128 (12) |
O08···C2A | 3.918 (6) | H05···H07a | 2.8431 (8) |
O08···C2B | 3.594 (6) | H05···H07b | 2.5090 (9) |
O08···H01 | 3.188 (3) | H05···H2G | 2.538 (2) |
O08···H07a | 2.812 (4) | H05···H2D2a | 3.235 (2) |
O08···H07b | 2.370 (3) | H05···H2D2c | 3.2536 (19) |
O08···H1A | 3.878 (4) | H05···H2b | 2.7251 (9) |
O08···H1A | 2.924 (3) | H07a···H07b | 1.5512 (7) |
O08···H1Ba | 3.614 (3) | H07a···H1Bb | 2.8629 (8) |
O08···H1Bb | 3.319 (4) | H07a···H1Ga | 3.2121 (13) |
O08···H1Ga | 2.851 (3) | H07a···H1Gb | 3.0062 (11) |
O08···H1Da | 2.631 (3) | H07a···H2c | 3.5020 (19) |
O08···H1Da | 3.816 (4) | H07a···H2b | 2.6874 (14) |
O08···H1Db | 3.129 (4) | H07a···H | 2.385 (4) |
O08···H1Db | 3.167 (4) | H07b···H2Ba | 2.942 (2) |
O08···H2Ba | 3.407 (4) | H07b···H2Bb | 3.193 (3) |
O08···H2Bb | 3.067 (4) | H07b···H2D1c | 3.5812 (15) |
O08···N2 | 3.044 (5) | H07b···H2b | 2.984 (3) |
O08···H2 | 2.126 (3) | H07b···H2 | 3.539 (2) |
N1···C1B | 3.572 (8) | H07b···H | 3.578 (4) |
N1···C1B | 2.367 (7) | H1A···H1Ba | 2.753 (2) |
N1···C1G | 4.140 (9) | H1A···H1Ba | 2.6450 (14) |
N1···C1G | 2.304 (7) | H1A···H1Bb | 2.2059 (8) |
N1···C1 | 2.460 (6) | H1A···H1Ga | 2.460 (2) |
N1···O1 | 2.868 (5) | H1A···H1Gb | 3.0321 (8) |
N1···N2 | 3.996 (6) | H1A···H1Da | 3.627 (2) |
N1···N2 | 3.608 (6) | H1A···H1Da | 3.4849 (18) |
N1···C2B | 4.052 (6) | H1A···H2 | 2.1980 (8) |
N1···O2 | 3.646 (6) | H1Ba···H1Bb | 3.555 (3) |
N1···H07a | 3.836 (5) | H1Ba···H1Bb | 1.5513 (9) |
N1···H07b | 3.753 (4) | H1Ba···H1Ga | 2.1781 (7) |
N1···H1A | 2.000 (4) | H1Ba···H1Gb | 2.7395 (14) |
N1···H1Ba | 2.849 (4) | H1Ba···H1Gb | 2.695 (2) |
N1···H1Ba | 2.896 (4) | H1Ba···H1Da | 3.0903 (17) |
N1···H1Bb | 3.565 (5) | H1Ba···H1Db | 2.9587 (18) |
N1···H1Bb | 3.089 (4) | H1Ba···H1Db | 3.632 (2) |
N1···H1Ga | 3.095 (4) | H1Ba···H2 | 3.5675 (11) |
N1···H1Ga | 3.645 (4) | H1Ba···H | 3.579 (4) |
N1···H1Gb | 2.718 (4) | H1Bb···H1Ga | 2.4924 (13) |
N1···H1Da | 2.014 (4) | H1Bb···H1Gb | 2.1757 (10) |
N1···H1Db | 2.014 (4) | H1Bb···H1Da | 2.8834 (16) |
N1···H2Bb | 3.169 (4) | H1Bb···H1Db | 2.8932 (17) |
N1···H2 | 3.255 (4) | H1Bb···H2 | 3.3562 (9) |
N1···H2 | 3.779 (4) | H1Bb···H | 3.146 (4) |
N1···H | 3.652 (6) | H1Ga···H1Gb | 1.5513 (13) |
C1A···C1B | 3.874 (8) | H1Ga···H1Da | 2.5228 (13) |
C1A···C1G | 2.390 (7) | H1Ga···H1Db | 2.2249 (7) |
C1A···C1G | 4.035 (10) | H1Ga···H2c | 3.0835 (17) |
C1A···C1D | 4.412 (7) | H1Gb···H1Da | 2.2191 (11) |
C1A···C1D | 2.440 (7) | H1Gb···H1Db | 2.7742 (10) |
C1A···O1 | 2.409 (6) | H1Gb···H2c | 2.3792 (7) |
C1A···N2 | 2.414 (6) | H1Gb···H | 3.166 (4) |
C1A···C2A | 3.795 (6) | H1Da···H1Db | 3.274 (3) |
C1A···C2 | 4.393 (7) | H1Da···H1Db | 1.5512 (12) |
C1A···O2 | 4.134 (6) | H1Da···H2c | 3.0474 (8) |
C1A···H01 | 3.761 (5) | H1Da···H2 | 3.4088 (9) |
C1A···H1Ba | 3.113 (5) | H1Da···H | 3.189 (4) |
C1A···H1Ba | 2.070 (5) | H1Db···H2 | 3.0306 (8) |
C1A···H1Bb | 2.070 (4) | H1Db···H | 3.093 (4) |
C1A···H1Ga | 3.333 (6) | H2A···H2Ba | 2.3199 (14) |
C1A···H1Ga | 3.174 (4) | H2A···H2Bb | 2.7920 (15) |
C1A···H1Gb | 2.810 (4) | H2A···H2G | 3.623 (2) |
C1A···H1Da | 4.021 (5) | H2A···H2G | 3.0800 (18) |
C1A···H1Da | 3.173 (4) | H2A···H2D1a | 3.5215 (12) |
C1A···H1Db | 3.973 (5) | H2A···H2D1b | 2.7821 (13) |
C1A···H1Db | 2.936 (5) | H2A···H2D2b | 2.9398 (8) |
C1A···H2Bb | 3.771 (4) | H2A···H2D2c | 2.2363 (6) |
C1A···H2 | 2.491 (4) | H2A···H2c | 2.2587 (11) |
C1A···H | 3.824 (6) | H2A···H2b | 2.3434 (13) |
C1B···C1G | 4.192 (11) | H2A···H2 | 2.7074 (11) |
C1B···C1D | 4.093 (9) | H2Ba···H2Bb | 1.5514 (5) |
C1B···C1D | 4.116 (9) | H2Ba···H2G | 2.7702 (18) |
C1B···C1D | 2.408 (8) | H2Ba···H2D1a | 3.4710 (13) |
C1B···C1 | 2.509 (6) | H2Ba···H2D1b | 2.8807 (17) |
C1B···O1 | 3.135 (6) | H2Ba···H2D1c | 2.4231 (9) |
C1B···N2 | 3.318 (6) | H2Ba···H2D2a | 3.5136 (14) |
C1B···O2 | 4.359 (7) | H2Ba···H2D2b | 2.4878 (7) |
C1B···O2 | 4.248 (7) | H2Ba···H2D2c | 2.9463 (19) |
C1B···H07a | 3.466 (5) | H2Ba···H2b | 3.555 (3) |
C1B···H1A | 2.060 (6) | H2Ba···H2 | 2.5061 (7) |
C1B···H1A | 3.295 (6) | H2Bb···H2G | 2.2883 (12) |
C1B···H1Ba | 3.554 (7) | H2Bb···H2D1a | 3.4623 (9) |
C1B···H1Ga | 2.009 (6) | H2Bb···H2D1b | 2.4106 (9) |
C1B···H1Gb | 3.619 (7) | H2Bb···H2D1c | 2.8631 (8) |
C1B···H1Gb | 2.009 (6) | H2Bb···H2D2b | 3.5109 (9) |
C1B···H1Da | 3.826 (7) | H2Bb···H2D2c | 3.5093 (11) |
C1B···H1Da | 3.729 (7) | H2Bb···H2c | 3.601 (2) |
C1B···H1Da | 3.189 (6) | H2Bb···H2b | 2.935 (3) |
C1B···H1Db | 2.831 (6) | H2Bb···H2 | 2.3717 (10) |
C1B···H1Db | 3.580 (7) | H2Bb···H | 2.799 (4) |
C1B···H2 | 3.379 (5) | H2G···H2D1a | 2.2947 (8) |
C1B···H | 3.893 (7) | H2G···H2D1b | 2.2781 (15) |
C1G···C1 | 4.410 (10) | H2G···H2D1c | 2.765 (2) |
C1G···C1 | 3.596 (7) | H2G···H2D2a | 2.2923 (6) |
C1G···O1 | 3.996 (7) | H2G···H2D2b | 2.7678 (10) |
C1G···O1 | 3.986 (8) | H2G···H2D2c | 2.2862 (12) |
C1G···C2 | 3.845 (8) | H2G···H2b | 2.2958 (8) |
C1G···O2 | 4.362 (8) | H2G···H | 3.064 (4) |
C1G···O2 | 3.832 (8) | H2D1a···H2D1b | 1.5515 (4) |
C1G···H01 | 3.955 (6) | H2D1a···H2D1c | 1.5513 (10) |
C1G···H07a | 3.372 (7) | H2D1a···H2D2a | 2.4025 (12) |
C1G···H1A | 2.896 (7) | H2D1a···H2D2a | 2.5662 (7) |
C1G···H1A | 3.214 (8) | H2D1a···H2D2b | 3.496 (2) |
C1G···H1Ba | 2.016 (7) | H2D1a···H2D2b | 2.8809 (19) |
C1G···H1Ba | 3.248 (8) | H2D1a···H2D2b | 3.1610 (11) |
C1G···H1Bb | 2.016 (7) | H2D1a···H2D2c | 3.2861 (10) |
C1G···H1Da | 2.052 (7) | H2D1a···H2D2c | 3.4580 (19) |
C1G···H1Db | 2.052 (7) | H2D1a···H2D2c | 3.578 (2) |
C1G···H2c | 3.055 (7) | H2D1b···H2D1c | 1.5514 (5) |
C1G···H | 3.902 (8) | H2D1b···H2D2a | 3.4607 (13) |
C1D···C1 | 3.491 (7) | H2D1b···H2D2b | 3.5023 (18) |
C1D···O1 | 3.647 (6) | H2D1c···H2D2a | 2.902 (2) |
C1D···N2 | 4.014 (7) | H2D1c···H2D2b | 2.4786 (13) |
C1D···C2 | 4.049 (7) | H2D1c···H2D2c | 3.503 (2) |
C1D···O2 | 3.528 (7) | H2D2a···H2D2b | 3.1463 (12) |
C1D···O2 | 3.493 (6) | H2D2a···H2D2b | 1.5514 (9) |
C1D···H1A | 3.974 (6) | H2D2a···H2D2c | 1.5513 (6) |
C1D···H1A | 3.066 (5) | H2D2a···H2D2c | 3.5266 (10) |
C1D···H1A | 3.995 (6) | H2D2b···H2D2c | 1.5513 (12) |
C1D···H1Ba | 3.261 (6) | H2D2c···H2b | 2.8227 (8) |
C1D···H1Ba | 2.835 (5) | H2c···H2b | 1.5513 (6) |
C1D···H1Bb | 3.185 (6) | H2c···H2 | 3.353 (3) |
C1D···H1Bb | 3.330 (6) | H2c···H | 2.559 (4) |
C1D···H1Ga | 2.035 (5) | H2b···H | 2.001 (4) |
C1D···H1Gb | 2.036 (5) | ||
C01—C06—C05 | 116.9 (6) | N1—C1D—C1G | 101.8 (4) |
C01—C06—C07 | 123.8 (5) | N1—C1D—H1Da | 111.4 (5) |
C05—C06—C07 | 119.4 (6) | N1—C1D—H1Db | 111.4 (5) |
C06—C01—C02 | 119.9 (6) | C1G—C1D—H1Da | 111.4 (5) |
C06—C01—H01 | 120.1 (6) | C1G—C1D—H1Db | 111.4 (5) |
C02—C01—H01 | 120.0 (7) | H1Da—C1D—H1Db | 109.5 (5) |
C01—C02—C03 | 122.8 (8) | C1A—C1—O1 | 123.0 (4) |
C01—C02—H02 | 118.6 (8) | C1A—C1—N2 | 115.9 (4) |
C03—C02—H02 | 118.6 (9) | O1—C1—N2 | 120.6 (4) |
C02—C03—C04 | 118.4 (8) | C1—N2—C2A | 124.8 (4) |
C02—C03—H03 | 120.8 (10) | C1—N2—H2 | 117.6 (4) |
C04—C03—H03 | 120.8 (9) | C2A—N2—H2 | 117.6 (4) |
C03—C04—C05 | 119.3 (8) | N2—C2A—C2B | 108.2 (4) |
C03—C04—H04 | 120.3 (10) | N2—C2A—C2 | 109.2 (4) |
C05—C04—H04 | 120.3 (12) | N2—C2A—H2A | 108.5 (4) |
C06—C05—C04 | 122.6 (8) | C2B—C2A—C2 | 113.8 (4) |
C06—C05—H05 | 118.7 (7) | C2B—C2A—H2A | 108.5 (4) |
C04—C05—H05 | 118.7 (8) | C2—C2A—H2A | 108.5 (4) |
C06—C07—O01 | 108.5 (4) | C2A—C2B—C2G | 117.1 (4) |
C06—C07—H07a | 109.7 (5) | C2A—C2B—H2Ba | 107.5 (4) |
C06—C07—H07b | 109.7 (5) | C2A—C2B—H2Bb | 107.5 (4) |
O01—C07—H07a | 109.7 (4) | C2G—C2B—H2Ba | 107.5 (4) |
O01—C07—H07b | 109.7 (5) | C2G—C2B—H2Bb | 107.5 (5) |
H07a—C07—H07b | 109.5 (6) | H2Ba—C2B—H2Bb | 109.5 (5) |
C07—O01—C08 | 114.3 (4) | C2B—C2G—C2D1 | 109.8 (5) |
O01—C08—O08 | 121.3 (4) | C2B—C2G—C2D2 | 111.4 (6) |
O01—C08—N1 | 110.8 (4) | C2B—C2G—H2G | 108.5 (4) |
O08—C08—N1 | 127.9 (5) | C2D1—C2G—C2D2 | 110.0 (5) |
C08—N1—C1A | 125.9 (4) | C2D1—C2G—H2G | 108.5 (6) |
C08—N1—C1D | 120.9 (4) | C2D2—C2G—H2G | 108.5 (6) |
C1A—N1—C1D | 112.6 (4) | C2G—C2D1—H2D1a | 109.5 (6) |
N1—C1A—C1B | 104.0 (4) | C2G—C2D1—H2D1b | 109.5 (6) |
N1—C1A—C1 | 112.0 (4) | C2G—C2D1—H2D1c | 109.5 (6) |
N1—C1A—H1A | 109.7 (4) | H2D1a—C2D1—H2D1b | 109.5 (7) |
C1B—C1A—C1 | 111.6 (4) | H2D1a—C2D1—H2D1c | 109.5 (7) |
C1B—C1A—H1A | 109.8 (4) | H2D1b—C2D1—H2D1c | 109.5 (7) |
C1—C1A—H1A | 109.7 (4) | C2G—C2D2—H2D2a | 109.5 (8) |
C1A—C1B—C1G | 105.0 (5) | C2G—C2D2—H2D2b | 109.5 (8) |
C1A—C1B—H1Ba | 110.6 (4) | C2G—C2D2—H2D2c | 109.5 (6) |
C1A—C1B—H1Bb | 110.6 (5) | H2D2a—C2D2—H2D2b | 109.5 (7) |
C1G—C1B—H1Ba | 110.6 (6) | H2D2a—C2D2—H2D2c | 109.5 (10) |
C1G—C1B—H1Bb | 110.6 (5) | H2D2b—C2D2—H2D2c | 109.5 (9) |
H1Ba—C1B—H1Bb | 109.5 (6) | C2A—C2—O2 | 114.9 (4) |
C1B—C1G—C1D | 107.7 (5) | C2A—C2—H2c | 108.1 (4) |
C1B—C1G—H1Ga | 109.9 (7) | C2A—C2—H2b | 108.1 (4) |
C1B—C1G—H1Gb | 109.9 (6) | O2—C2—H2c | 108.1 (4) |
C1D—C1G—H1Ga | 109.9 (6) | O2—C2—H2b | 108.1 (4) |
C1D—C1G—H1Gb | 109.9 (6) | H2c—C2—H2b | 109.5 (5) |
H1Ga—C1G—H1Gb | 109.5 (6) | C2—O2—H | 108.7 (4) |
C05—C06—C01—C02 | −1.0 (10) | C1A—C1B—C1G—H1Ga | 148.0 (5) |
C05—C06—C01—H01 | 179.0 (7) | C1A—C1B—C1G—H1Gb | −91.5 (6) |
C07—C06—C01—C02 | 178.7 (6) | H1Ba—C1B—C1G—C1D | −91.0 (6) |
C07—C06—C01—H01 | −1.3 (11) | H1Ba—C1B—C1G—H1Ga | 28.7 (8) |
C01—C06—C05—C04 | −0.0 (10) | H1Ba—C1B—C1G—H1Gb | 149.2 (6) |
C01—C06—C05—H05 | 180.0 (6) | H1Bb—C1B—C1G—C1D | 147.6 (6) |
C07—C06—C05—C04 | −179.7 (7) | H1Bb—C1B—C1G—H1Ga | −92.7 (7) |
C07—C06—C05—H05 | 0.3 (10) | H1Bb—C1B—C1G—H1Gb | 27.8 (8) |
C01—C06—C07—O01 | −16.5 (7) | C1B—C1G—C1D—H1Da | −148.3 (5) |
C01—C06—C07—H07a | 103.4 (7) | C1B—C1G—C1D—H1Db | 89.2 (6) |
C01—C06—C07—H07b | −136.3 (6) | H1Ga—C1G—C1D—N1 | −149.3 (5) |
C05—C06—C07—O01 | 163.2 (5) | H1Ga—C1G—C1D—H1Da | 91.9 (7) |
C05—C06—C07—H07a | −76.9 (7) | H1Ga—C1G—C1D—H1Db | −30.6 (8) |
C05—C06—C07—H07b | 43.4 (7) | H1Gb—C1G—C1D—N1 | 90.2 (6) |
C06—C01—C02—C03 | 3.2 (13) | H1Gb—C1G—C1D—H1Da | −28.6 (8) |
C06—C01—C02—H02 | −176.8 (7) | H1Gb—C1G—C1D—H1Db | −151.1 (6) |
H01—C01—C02—C03 | −176.8 (8) | C1A—C1—N2—H2 | −8.7 (6) |
H01—C01—C02—H02 | 3.2 (13) | O1—C1—N2—C2A | −1.4 (7) |
C01—C02—C03—C04 | −4.2 (14) | O1—C1—N2—H2 | 178.6 (4) |
C01—C02—C03—H03 | 175.8 (9) | C1—N2—C2A—C2B | 157.8 (4) |
H02—C02—C03—C04 | 175.8 (9) | C1—N2—C2A—H2A | 40.3 (6) |
H02—C02—C03—H03 | −4.2 (15) | H2—N2—C2A—C2B | −22.2 (5) |
C02—C03—C04—C05 | 3.1 (14) | H2—N2—C2A—C2 | 102.2 (5) |
C02—C03—C04—H04 | −176.9 (9) | H2—N2—C2A—H2A | −139.7 (4) |
H03—C03—C04—C05 | −177.0 (9) | N2—C2A—C2B—C2G | −177.2 (4) |
H03—C03—C04—H04 | 3.0 (16) | N2—C2A—C2B—H2Ba | −56.1 (5) |
C03—C04—C05—C06 | −1.0 (13) | N2—C2A—C2B—H2Bb | 61.6 (5) |
C03—C04—C05—H05 | 179.0 (8) | C2—C2A—C2B—C2G | 61.2 (5) |
H04—C04—C05—C06 | 179.0 (8) | C2—C2A—C2B—H2Ba | −177.7 (4) |
H04—C04—C05—H05 | −1.0 (14) | C2—C2A—C2B—H2Bb | −59.9 (5) |
C06—C07—O01—C08 | −164.0 (4) | H2A—C2A—C2B—C2G | −59.7 (6) |
H07a—C07—O01—C08 | 76.1 (6) | H2A—C2A—C2B—H2Ba | 61.4 (5) |
H07b—C07—O01—C08 | −44.1 (6) | H2A—C2A—C2B—H2Bb | 179.2 (4) |
C07—O01—C08—O08 | 6.6 (6) | N2—C2A—C2—H2c | 66.9 (5) |
C07—O01—C08—N1 | −174.0 (4) | N2—C2A—C2—H2b | −174.7 (4) |
O01—C08—N1—C1A | 0.5 (6) | C2B—C2A—C2—O2 | 67.1 (5) |
O01—C08—N1—C1D | 171.6 (4) | C2B—C2A—C2—H2c | −172.1 (4) |
O08—C08—N1—C1A | 179.9 (5) | C2B—C2A—C2—H2b | −53.7 (5) |
O08—C08—N1—C1D | −9.0 (8) | H2A—C2A—C2—O2 | −172.0 (4) |
C08—N1—C1A—C1B | 168.1 (5) | H2A—C2A—C2—H2c | −51.2 (6) |
C08—N1—C1A—C1 | −71.3 (6) | H2A—C2A—C2—H2b | 67.2 (5) |
C08—N1—C1A—H1A | 50.8 (6) | C2A—C2B—C2G—C2D1 | −179.2 (5) |
C1D—N1—C1A—C1 | 117.0 (4) | C2A—C2B—C2G—C2D2 | 58.7 (7) |
C1D—N1—C1A—H1A | −120.9 (4) | C2A—C2B—C2G—H2G | −60.7 (7) |
C08—N1—C1D—C1G | −152.1 (5) | H2Ba—C2B—C2G—C2D1 | 59.7 (6) |
C08—N1—C1D—H1Da | −33.3 (7) | H2Ba—C2B—C2G—C2D2 | −62.4 (7) |
C08—N1—C1D—H1Db | 89.2 (6) | H2Ba—C2B—C2G—H2G | 178.1 (5) |
C1A—N1—C1D—H1Da | 138.9 (4) | H2Bb—C2B—C2G—C2D1 | −58.1 (6) |
C1A—N1—C1D—H1Db | −98.6 (5) | H2Bb—C2B—C2G—C2D2 | 179.8 (6) |
N1—C1A—C1B—H1Ba | 104.2 (5) | H2Bb—C2B—C2G—H2G | 60.4 (6) |
N1—C1A—C1B—H1Bb | −134.4 (5) | C2B—C2G—C2D1—H2D1a | 180.0 (5) |
C1—C1A—C1B—C1G | −135.9 (5) | C2B—C2G—C2D1—H2D1b | 60.0 (7) |
C1—C1A—C1B—H1Ba | −16.6 (7) | C2B—C2G—C2D1—H2D1c | −60.0 (7) |
C1—C1A—C1B—H1Bb | 104.8 (5) | C2D2—C2G—C2D1—H2D1a | −57.1 (8) |
H1A—C1A—C1B—C1G | 102.2 (5) | C2D2—C2G—C2D1—H2D1b | −177.1 (7) |
H1A—C1A—C1B—H1Ba | −138.5 (5) | C2D2—C2G—C2D1—H2D1c | 63.0 (8) |
H1A—C1A—C1B—H1Bb | −17.1 (7) | H2G—C2G—C2D1—H2D1a | 61.6 (7) |
N1—C1A—C1—O1 | −41.4 (6) | H2G—C2G—C2D1—H2D1b | −58.4 (7) |
N1—C1A—C1—N2 | 146.1 (4) | H2G—C2G—C2D1—H2D1c | −178.4 (5) |
C1A—C1—N2—C2A | 171.2 (4) | C2B—C2G—C2D2—H2D2a | −180.0 (7) |
C1—N2—C2A—C2 | −77.8 (5) | C2B—C2G—C2D2—H2D2b | 60.0 (8) |
N2—C2A—C2—O2 | −53.9 (5) | C2B—C2G—C2D2—H2D2c | −60.0 (10) |
C1B—C1A—C1—O1 | 74.7 (6) | C2D1—C2G—C2D2—H2D2a | 58.0 (10) |
C1B—C1A—C1—N2 | −97.8 (5) | C2D1—C2G—C2D2—H2D2b | −62.0 (8) |
H1A—C1A—C1—O1 | −163.5 (4) | C2D1—C2G—C2D2—H2D2c | 178.0 (7) |
H1A—C1A—C1—N2 | 24.0 (6) | H2G—C2G—C2D2—H2D2a | −60.6 (9) |
C1A—C1B—C1G—C1D | 28.3 (7) | H2G—C2G—C2D2—H2D2b | 179.4 (6) |
C1B—C1G—C1D—N1 | −29.6 (6) | H2G—C2G—C2D2—H2D2c | 59.4 (9) |
C1A—N1—C1D—C1G | 20.1 (5) | C2A—C2—O2—H | −103.6 (5) |
C1D—N1—C1A—C1B | −3.6 (5) | H2c—C2—O2—H | 135.5 (5) |
N1—C1A—C1B—C1G | −15.1 (6) | H2b—C2—O2—H | 17.1 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2 | 0.92 | 2.13 (1) | 3.044 (5) | 176 |
O2—H···O1 | 0.89 | 2.05 (1) | 2.733 (5) | 132 |
Experimental details
Crystal data | |
Chemical formula | C19H28N2O4 |
Mr | 348.44 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 6.371 (4), 8.824 (8), 34.303 (10) |
V (Å3) | 1928 (2) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.68 |
Crystal size (mm) | 1.0 × 0.4 × 0.2 |
Data collection | |
Diffractometer | CAD-4 diffractometer |
Absorption correction | Analytical (Xtal3.7 ABSORB; Hall et al., 2000) |
Tmin, Tmax | 0.736, 0.875 |
No. of measured, independent and observed [I > 2.5σ(I)] reflections | 4821, 2111, 1398 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.610 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.093, 2.00 |
No. of reflections | 2049 |
No. of parameters | 227 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.39, −0.49 |
Absolute structure | Assumed from synthesis, see text |
Computer programs: CAD-4 Software (Enraf Nonius, 1989), CAD-4 Software, Xtal3.7 DIFDAT ABSORB ADDREF (Hall et al., 2000), Xtal3.7 CRISP, Xtal3.7 CRILSQ, Xtal3.7 BONDLA CIFIO.
C06—C07—O01—C08 | −164.0 (4) | C1A—C1B—C1G—C1D | 28.3 (7) |
C07—O01—C08—N1 | −174.0 (4) | C1B—C1G—C1D—N1 | −29.6 (6) |
O01—C08—N1—C1A | 0.5 (6) | C1A—N1—C1D—C1G | 20.1 (5) |
C08—N1—C1A—C1 | −71.3 (6) | C1D—N1—C1A—C1B | −3.6 (5) |
N1—C1A—C1—N2 | 146.1 (4) | N1—C1A—C1B—C1G | −15.1 (6) |
C1A—C1—N2—C2A | 171.2 (4) | N2—C2A—C2B—C2G | −177.2 (4) |
C1—N2—C2A—C2 | −77.8 (5) | C2A—C2B—C2G—C2D1 | −179.2 (5) |
N2—C2A—C2—O2 | −53.9 (5) | C2A—C2B—C2G—C2D2 | 58.7 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2 | 0.92 | 2.126 (3) | 3.044 (5) | 175.61 |
O2—H···O1 | 0.892 | 2.053 (5) | 2.733 (5) | 132.14 |
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The sequence Pro-Leucinol is the C-terminal dipeptide of several naturally occurring peptaibols, i.e. peptides containing α-aminoisobutyric acid (Aib) and an alcoholic C-terminus (Brückner & Graf, 1983; Benedetti et al., 1982), among them harzianin (Rebuffat et al., 1994, 1995), hypomuricin (Becker, 1996; Becker et al., 1997) and trichovirin (Kieß and Brückner, 1990; Brückner et al., 1991). The crystal structures of the four, eight and twelve C-terminal residues comprising peptides of trichovirin were solved by our group (Geßmann et al., 1994, 1999). Interestingely, while proline in the longer peptides adopts main-chain torsion angles ϕ and ψ which lie in the 310-helical region, proline in the dipeptide adopts a semi-extended conformation with ϕ and ψ values of −71.3 and 146.1°, respectively. The ϕ values of Leu in the longer peptides have been observed as unusually small for the helical region, while the ϕ value (−77.8°) of Leu in the title compound, (I), lies inside the helical region. The pyrrolidine ring of Pro adopts the Cγ-exo (Ashida & Kakudo, 1974) conformation, with puckering parameters (Cremer & Pople, 1975) Q = 0.284 Å and Φ = 292.98°. In the crystal, the peptides are hydrogen bonded along the [100] direction via two hydrogen bonds (see Table 2). In the other directions, these columns of molecules are packed via apolar crystal contacts. \scheme