Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100010830/gs1100sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010830/gs1100IIsup2.hkl |
CCDC reference: 158249
Le dipeptide linéaire (I) est préparé par réaction de couplage du β-amino acide avec la L-alanine. Le composé (II) a été obtenue par cyclization du composé (I) en présence de BOP/DIEA. La cristallization de (II) a été effectuée à température ambiante à partir d'un mélange d'acétate d'éthyle et d'hexane.
Les atomes d'hydrogène sont en position théorique et ont été affinés. Ils sont contraints a l'atome parent avec un paramètre de déplacement isotrope U(H)eq = Ueq + 0.02 de l'atome parent [option parent + de maXus (Mackay et al. 1999)]. [Please provide some details of what were done with the Friedel data, i.e. was the original Friedel data set merged ? Is there a Flack parameter value ? Also please supply details of the fixed C—H distances].
Data collection: KappaCCD software; data reduction: DENZO and SCALEPAK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: maXus (Mackay et al., 1999); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: maXus (Mackay et al., 1999).
C17H20N2O6 | F(000) = 736 |
Mr = 348.36 | Dx = 1.279 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.0323 (7) Å | Cell parameters from 12894 reflections |
b = 11.7742 (4) Å | θ = 1.0–26.3° |
c = 14.1121 (9) Å | µ = 0.10 mm−1 |
β = 99.380 (2)° | T = 298 K |
V = 1808.6 (2) Å3 | Prism, colourless' |
Z = 4 | 0.32 × 0.27 × 0.10 mm |
KappaCCD diffractometer | Rint = 0.055 |
Radiation source: X-ray tube | θmax = 26.3° |
ϕ scan | h = −13→13 |
11340 measured reflections | k = −12→13 |
3708 independent reflections | l = −16→17 |
3033 reflections with I > 2.5σ(I) |
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)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.048 | w = 1/[s2(Fo2) + 0.03Fo2] |
S = 1.22 | (Δ/σ)max = 0.004 |
3033 reflections | Δρmax = 0.17 e Å−3 |
374 parameters | Δρmin = −0.16 e Å−3 |
Primary atom site location: structure-invariant direct methods |
C17H20N2O6 | V = 1808.6 (2) Å3 |
Mr = 348.36 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 11.0323 (7) Å | µ = 0.10 mm−1 |
b = 11.7742 (4) Å | T = 298 K |
c = 14.1121 (9) Å | 0.32 × 0.27 × 0.10 mm |
β = 99.380 (2)° |
KappaCCD diffractometer | 3033 reflections with I > 2.5σ(I) |
11340 measured reflections | Rint = 0.055 |
3708 independent reflections |
R[F2 > 2σ(F2)] = 0.052 | 374 parameters |
wR(F2) = 0.048 | H-atom parameters constrained |
S = 1.22 | Δρmax = 0.17 e Å−3 |
3033 reflections | Δρmin = −0.16 e Å−3 |
Geometry. All standard uncertainties (except dihedral angles between l.s. planes) are estimated using the full covariance matrix. The standard uncertainties in cell dimensions are are used in calculating the standard uncertainties of bond distances, angles and torsion angles. Angles between l.s. planes have standard uncertainties calculated from atomic positional standard uncertainties; the errors in cell dimensions are not used in this case. |
Refinement. Refinement on F2. |
x | y | z | Uiso*/Ueq | ||
O1A | 0.33898 (7) | 0.5013 (2) | 0.25187 (5) | 0.0595 (5) | |
O2A | 0.17861 (7) | 0.55186 (9) | 0.32227 (5) | 0.0557 (4) | |
O3A | 0.4065 (1) | 0.8948 (1) | 0.35387 (8) | 0.1398 (8) | |
O4A | 0.41121 (7) | 0.7107 (1) | 0.37530 (5) | 0.0713 (5) | |
O5A | 0.35876 (9) | 0.8829 (1) | 0.11625 (7) | 0.1178 (7) | |
O6A | 0.05453 (7) | 0.94169 (9) | 0.29109 (5) | 0.0626 (5) | |
N18A | 0.12957 (8) | 1.0542 (1) | 0.18050 (6) | 0.0571 (5) | |
N19A | 0.21122 (8) | 0.88505 (9) | 0.21295 (6) | 0.0505 (5) | |
C1A | 0.3637 (1) | 0.8058 (1) | 0.33741 (8) | 0.0619 (7) | |
C2A | 0.24380 (9) | 0.7832 (1) | 0.26848 (7) | 0.0450 (5) | |
C3A | 0.24478 (9) | 0.6766 (1) | 0.20630 (6) | 0.0407 (5) | |
C4A | 0.2500 (1) | 0.5716 (1) | 0.26819 (7) | 0.0426 (6) | |
C5A | 0.1258 (1) | 0.6695 (1) | 0.13152 (7) | 0.0525 (6) | |
C6A | 0.12154 (9) | 0.5672 (1) | 0.06741 (6) | 0.0449 (6) | |
C7A | 0.06794 (9) | 0.4676 (1) | 0.08968 (7) | 0.0559 (7) | |
C8A | 0.0680 (1) | 0.3709 (1) | 0.03286 (7) | 0.0594 (7) | |
C9A | 0.1211 (1) | 0.3754 (1) | −0.04823 (7) | 0.0586 (7) | |
C10A | 0.1746 (1) | 0.4754 (1) | −0.07171 (7) | 0.0603 (7) | |
C11A | 0.1745 (1) | 0.5699 (1) | −0.01526 (7) | 0.0516 (6) | |
C12A | 0.2746 (1) | 0.9282 (1) | 0.14554 (8) | 0.0698 (7) | |
C13A | 0.2206 (1) | 1.0439 (1) | 0.11681 (8) | 0.0663 (7) | |
C14A | 0.12206 (9) | 0.9618 (1) | 0.23371 (7) | 0.0463 (6) | |
C15A | 0.3147 (1) | 1.1355 (1) | 0.1286 (1) | 0.1067 (9) | |
C16A | 0.5249 (1) | 0.7200 (2) | 0.44449 (9) | 0.101 (1) | |
C17A | 0.3440 (1) | 0.3957 (1) | 0.3052 (1) | 0.103 (1) | |
O1B | 0.65409 (7) | 0.65575 (6) | 0.24134 (5) | 0.0643 (5) | |
O2B | 0.80389 (7) | 0.6068 (1) | 0.16013 (5) | 0.0705 (5) | |
O3B | 0.59637 (8) | 0.2651 (1) | 0.10461 (6) | 0.0871 (6) | |
O4B | 0.57374 (7) | 0.4529 (1) | 0.11556 (5) | 0.0659 (5) | |
O5B | 0.60220 (7) | 0.2526 (1) | 0.33151 (6) | 0.0887 (5) | |
O6B | 0.95963 (7) | 0.23090 (9) | 0.21082 (5) | 0.0573 (4) | |
N18B | 0.86741 (8) | 0.1071 (1) | 0.30372 (6) | 0.0567 (5) | |
N19B | 0.77533 (7) | 0.26960 (9) | 0.26239 (5) | 0.0460 (5) | |
C1B | 0.6303 (1) | 0.3569 (1) | 0.13773 (8) | 0.0563 (7) | |
C2B | 0.7476 (1) | 0.3750 (1) | 0.20979 (6) | 0.0451 (6) | |
C3B | 0.74609 (9) | 0.4773 (1) | 0.27654 (6) | 0.0436 (6) | |
C4B | 0.7389 (1) | 0.5843 (1) | 0.21816 (7) | 0.0499 (6) | |
C5B | 0.8652 (1) | 0.4822 (1) | 0.35164 (7) | 0.0584 (7) | |
C6B | 0.8710 (1) | 0.5830 (1) | 0.41788 (7) | 0.0526 (6) | |
C7B | 0.9237 (1) | 0.6845 (1) | 0.39594 (8) | 0.0639 (7) | |
C8B | 0.9276 (1) | 0.7759 (1) | 0.45667 (9) | 0.0724 (8) | |
C9B | 0.8785 (1) | 0.7706 (1) | 0.53949 (8) | 0.0682 (8) | |
C10B | 0.8263 (1) | 0.6715 (1) | 0.56267 (8) | 0.0693 (8) | |
C11B | 0.8226 (1) | 0.5769 (1) | 0.50213 (8) | 0.0645 (7) | |
C12B | 0.6978 (1) | 0.2149 (1) | 0.31381 (7) | 0.0586 (6) | |
C13B | 0.7543 (1) | 0.1019 (1) | 0.34394 (7) | 0.0568 (6) | |
C14B | 0.8782 (1) | 0.2012 (1) | 0.25436 (7) | 0.0463 (6) | |
C15B | 0.7741 (1) | 0.0857 (1) | 0.45088 (8) | 0.0911 (9) | |
C16B | 0.4618 (1) | 0.4499 (1) | 0.04577 (8) | 0.0742 (8) | |
C17B | 0.6411 (2) | 0.7628 (2) | 0.1912 (1) | 0.121 (1) | |
H2A | 0.182342 | 0.767632 | 0.307673 | 0.065032* | |
H3A | 0.314503 | 0.678436 | 0.173547 | 0.059079* | |
H5A1 | 0.121008 | 0.737295 | 0.093232 | 0.071957* | |
H5A2 | 0.057752 | 0.667181 | 0.166032 | 0.071957* | |
H7A | 0.029232 | 0.465611 | 0.145854 | 0.076515* | |
H8A | 0.031778 | 0.301480 | 0.050404 | 0.078979* | |
H9A | 0.121171 | 0.309928 | −0.088807 | 0.076866* | |
H10A | 0.212069 | 0.478091 | −0.128458 | 0.078865* | |
H11A | 0.211249 | 0.639149 | −0.032691 | 0.071694* | |
H13A | 0.180187 | 1.046887 | 0.051233 | 0.086387* | |
H15A1 | 0.276218 | 1.206913 | 0.109539 | 0.126568* | |
H15A2 | 0.375349 | 1.118896 | 0.088973 | 0.126568* | |
H15A3 | 0.353410 | 1.139753 | 0.194582 | 0.126568* | |
H16A1 | 0.550634 | 0.645629 | 0.467310 | 0.115766* | |
H16A2 | 0.511155 | 0.766456 | 0.497647 | 0.115766* | |
H16A3 | 0.587559 | 0.753776 | 0.413808 | 0.115766* | |
H17A1 | 0.410637 | 0.350123 | 0.290413 | 0.124271* | |
H17A2 | 0.268006 | 0.355635 | 0.286982 | 0.124271* | |
H17A3 | 0.356206 | 0.411022 | 0.372902 | 0.124271* | |
H18A | 0.077676 | 1.118517 | 0.186065 | 0.076786* | |
H2B | 0.811587 | 0.391652 | 0.173224 | 0.064361* | |
H3B | 0.676350 | 0.471870 | 0.309050 | 0.063546* | |
H5BA | 0.933227 | 0.484554 | 0.317066 | 0.076473* | |
H5BB | 0.868940 | 0.413468 | 0.388653 | 0.076473* | |
H7B | 0.957771 | 0.690343 | 0.337737 | 0.082441* | |
H8B | 0.965638 | 0.844730 | 0.439785 | 0.091550* | |
H9B | 0.880781 | 0.835390 | 0.581013 | 0.086752* | |
H10B | 0.791702 | 0.666893 | 0.620740 | 0.088845* | |
H11B | 0.786154 | 0.507278 | 0.518931 | 0.082101* | |
H13B | 0.705169 | 0.039184 | 0.316375 | 0.075802* | |
H15B1 | 0.810133 | 0.012547 | 0.466741 | 0.110110* | |
H15B2 | 0.696692 | 0.090614 | 0.473331 | 0.110110* | |
H15B3 | 0.828166 | 0.143872 | 0.480960 | 0.110110* | |
H16B1 | 0.428736 | 0.525200 | 0.035644 | 0.097248* | |
H16B2 | 0.402848 | 0.401852 | 0.069104 | 0.097248* | |
H16B3 | 0.479729 | 0.420249 | −0.013777 | 0.097248* | |
H17B1 | 0.578636 | 0.807324 | 0.213727 | 0.155445* | |
H17B2 | 0.617967 | 0.748973 | 0.123604 | 0.155445* | |
H17B3 | 0.717622 | 0.803258 | 0.202493 | 0.155445* | |
H18B | 0.930610 | 0.050358 | 0.309168 | 0.070012* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0625 (5) | 0.0456 (5) | 0.0705 (5) | −0.0262 (4) | 0.0231 (4) | −0.0118 (4) |
O2A | 0.0549 (5) | 0.0561 (5) | 0.0567 (4) | −0.0112 (4) | 0.0211 (4) | −0.0055 (4) |
O3A | 0.1211 (9) | 0.0672 (7) | 0.211 (1) | 0.0242 (6) | −0.0665 (8) | 0.0154 (7) |
O4A | 0.0590 (5) | 0.0744 (7) | 0.0739 (5) | −0.0091 (5) | −0.0182 (4) | 0.0033 (5) |
O5A | 0.1083 (7) | 0.0745 (6) | 0.1799 (9) | −0.0392 (6) | 0.1028 (7) | −0.0396 (6) |
O6A | 0.0635 (5) | 0.0544 (5) | 0.0724 (5) | −0.0180 (4) | 0.0351 (4) | −0.0059 (4) |
N18A | 0.0566 (6) | 0.0385 (6) | 0.0760 (6) | −0.0116 (5) | 0.0252 (5) | −0.0061 (5) |
N19A | 0.0514 (5) | 0.0353 (5) | 0.0652 (5) | −0.0123 (4) | 0.0236 (4) | −0.0025 (4) |
C1A | 0.0579 (7) | 0.0550 (8) | 0.0705 (8) | −0.0031 (7) | 0.0103 (6) | 0.0164 (6) |
C2A | 0.0368 (6) | 0.0477 (7) | 0.0500 (6) | −0.0095 (5) | 0.0113 (5) | 0.0025 (5) |
C3A | 0.0408 (6) | 0.0365 (6) | 0.0438 (5) | −0.0065 (5) | 0.0085 (4) | 0.0027 (4) |
C4A | 0.0409 (5) | 0.0406 (7) | 0.0445 (5) | −0.0103 (5) | 0.0020 (5) | 0.0050 (5) |
C5A | 0.0445 (6) | 0.0580 (8) | 0.0520 (6) | −0.0146 (6) | −0.0024 (5) | −0.0008 (5) |
C6A | 0.0397 (6) | 0.0479 (7) | 0.0440 (6) | −0.0096 (5) | −0.0042 (5) | −0.0008 (5) |
C7A | 0.0475 (7) | 0.0673 (9) | 0.0511 (6) | 0.0085 (6) | 0.0098 (5) | 0.0049 (6) |
C8A | 0.0622 (8) | 0.0515 (8) | 0.0625 (7) | 0.0076 (6) | 0.0070 (6) | 0.0110 (6) |
C9A | 0.0558 (7) | 0.0605 (8) | 0.0565 (7) | 0.0021 (6) | 0.0005 (5) | 0.0121 (6) |
C10A | 0.0584 (7) | 0.0752 (9) | 0.0465 (6) | −0.0016 (7) | 0.0087 (5) | 0.0022 (6) |
C11A | 0.0506 (7) | 0.0559 (8) | 0.0470 (6) | 0.0030 (6) | 0.0046 (5) | −0.0064 (5) |
C12A | 0.0633 (7) | 0.0505 (7) | 0.0985 (9) | −0.0123 (6) | 0.0426 (7) | −0.0114 (6) |
C13A | 0.0608 (7) | 0.0510 (8) | 0.0885 (8) | −0.0117 (6) | 0.0293 (6) | −0.0091 (6) |
C14A | 0.0451 (5) | 0.0406 (7) | 0.0526 (6) | −0.0083 (5) | 0.0134 (5) | 0.0057 (5) |
C15A | 0.0718 (8) | 0.0555 (8) | 0.194 (1) | 0.0012 (6) | 0.0518 (9) | −0.0262 (8) |
C16A | 0.0592 (8) | 0.164 (2) | 0.0754 (8) | −0.0092 (9) | −0.0198 (7) | 0.0146 (9) |
C17A | 0.114 (1) | 0.065 (1) | 0.130 (1) | −0.0571 (9) | 0.0412 (9) | −0.0273 (9) |
O1B | 0.0586 (5) | 0.0515 (5) | 0.0840 (5) | −0.0237 (4) | 0.0306 (4) | −0.0193 (4) |
O2B | 0.0606 (5) | 0.0642 (6) | 0.0883 (5) | −0.0153 (4) | 0.0355 (4) | −0.0204 (4) |
O3B | 0.0908 (6) | 0.0631 (6) | 0.1006 (6) | 0.0042 (5) | −0.0103 (5) | 0.0077 (5) |
O4B | 0.0518 (5) | 0.0749 (6) | 0.0660 (5) | −0.0258 (5) | −0.0109 (4) | 0.0106 (4) |
O5B | 0.0577 (5) | 0.0849 (6) | 0.1272 (7) | −0.0329 (4) | 0.0492 (5) | −0.0459 (5) |
O6B | 0.0544 (4) | 0.0469 (4) | 0.0717 (4) | −0.0142 (4) | 0.0318 (4) | −0.0084 (3) |
N18B | 0.0541 (6) | 0.0483 (6) | 0.0673 (6) | −0.0203 (5) | 0.0254 (4) | −0.0124 (5) |
N19B | 0.0421 (9) | 0.0368 (5) | 0.0600 (5) | −0.0089 (4) | 0.0179 (4) | −0.0097 (4) |
C1B | 0.0463 (9) | 0.0619 (8) | 0.0595 (7) | −0.0017 (6) | 0.0126 (5) | −0.0045 (6) |
C2B | 0.0452 (6) | 0.0379 (6) | 0.0511 (6) | −0.0086 (5) | 0.0109 (5) | −0.0093 (5) |
C3B | 0.0347 (6) | 0.0487 (7) | 0.0462 (6) | −0.0116 (5) | 0.0074 (4) | −0.0065 (5) |
C4B | 0.0404 (9) | 0.0443 (7) | 0.0639 (7) | −0.0092 (5) | 0.0138 (5) | −0.0073 (5) |
C5B | 0.0555 (7) | 0.0509 (8) | 0.0650 (7) | −0.0129 (6) | −0.0018 (5) | 0.0005 (6) |
C6B | 0.0428 (6) | 0.0573 (8) | 0.0549 (7) | −0.0093 (6) | −0.0010 (5) | 0.0005 (6) |
C7B | 0.0583 (8) | 0.0663 (9) | 0.0668 (7) | 0.0038 (7) | 0.0166 (6) | 0.0037 (7) |
C8B | 0.0650 (9) | 0.0665 (9) | 0.0843 (9) | 0.0137 (7) | 0.0141 (7) | 0.0048 (7) |
C9B | 0.0640 (8) | 0.0672 (9) | 0.0698 (8) | −0.0061 (7) | −0.0007 (6) | 0.0114 (7) |
C10B | 0.0745 (9) | 0.078 (1) | 0.0531 (7) | −0.0022 (8) | 0.0045 (6) | −0.0034 (7) |
C11B | 0.0698 (8) | 0.0621 (8) | 0.0565 (7) | 0.0007 (7) | −0.0082 (6) | −0.0087 (6) |
C12B | 0.0526 (9) | 0.0530 (7) | 0.0699 (7) | −0.0137 (5) | 0.0198 (5) | −0.0136 (5) |
C13B | 0.0600 (7) | 0.0486 (7) | 0.0635 (7) | −0.0101 (5) | 0.0254 (5) | −0.0132 (5) |
C14B | 0.0463 (9) | 0.0379 (7) | 0.0530 (6) | −0.0095 (5) | 0.0070 (5) | 0.0033 (5) |
C15B | 0.108 (1) | 0.090 (1) | 0.0761 (8) | −0.0465 (8) | 0.0380 (7) | −0.0302 (7) |
C16B | 0.0539 (7) | 0.099 (1) | 0.0647 (7) | −0.0171 (7) | −0.0087 (6) | −0.0044 (7) |
C17B | 0.125 (1) | 0.072 (1) | 0.173 (1) | −0.051 (1) | 0.082 (1) | −0.065 (1) |
O1A—C4A | 1.332 (1) | O1B—C4B | 1.338 (1) |
O1A—C17A | 1.447 (1) | O1B—C17B | 1.441 (2) |
O2A—C4A | 1.206 (1) | O2B—C4B | 1.203 (1) |
O3A—C1A | 1.157 (2) | O3B—C1B | 1.212 (1) |
O4A—C1A | 1.312 (1) | O4B—C1B | 1.305 (1) |
O4A—C16A | 1.462 (1) | O4B—C16B | 1.448 (1) |
O5A—C12A | 1.200 (1) | O5B—C12B | 1.208 (1) |
O6A—C14A | 1.209 (1) | O6B—C14B | 1.219 (1) |
N18A—C13A | 1.457 (1) | N18B—C13B | 1.454 (1) |
N18A—C14A | 1.333 (1) | N18B—C14B | 1.326 (1) |
N19A—C2A | 1.445 (1) | N19B—C2B | 1.453 (1) |
N19A—C12A | 1.367 (1) | N19B—C12B | 1.370 (1) |
N19A—C14A | 1.402 (1) | N19B—C14B | 1.411 (1) |
C1A—C2A | 1.533 (2) | C1B—C2B | 1.524 (1) |
C2A—C3A | 1.532 (1) | C2B—C3B | 1.531 (1) |
C3A—C4A | 1.509 (1) | C3B—C4B | 1.501 (1) |
C3A—C5A | 1.547 (1) | C3B—C5B | 1.548 (1) |
C5A—C6A | 1.502 (1) | C5B—C6B | 1.507 (1) |
C6A—C7A | 1.373 (1) | C6B—C7B | 1.385 (2) |
C6A—C11A | 1.388 (1) | C6B—C11B | 1.382 (2) |
C7A—C8A | 1.392 (2) | C7B—C8B | 1.373 (2) |
C8A—C9A | 1.369 (1) | C8B—C9B | 1.366 (2) |
C9A—C10A | 1.381 (2) | C9B—C10B | 1.364 (2) |
C10A—C11A | 1.369 (2) | C10B—C11B | 1.401 (2) |
C12A—C13A | 1.515 (2) | C12B—C13B | 1.500 (2) |
C13A—C15A | 1.485 (2) | C13B—C15B | 1.501 (1) |
C4A—O1A—C17A | 114.2 (1) | C4B—O1B—C17B | 116.6 (1) |
C1A—O4A—C16A | 116.8 (2) | C1B—O4B—C16B | 117.5 (1) |
C13A—N18A—C14A | 113.0 (1) | C13B—N18B—C14B | 113.3 (1) |
C2A—N19A—C12A | 125.2 (1) | C2B—N19B—C12B | 125.1 (1) |
C2A—N19A—C14A | 122.9 (1) | C2B—N19B—C14B | 123.5 (1) |
C12A—N19A—C14A | 111.2 (1) | C12B—N19B—C14B | 110.7 (1) |
O3A—C1A—O4A | 124.6 (2) | O3B—C1B—O4B | 125.0 (2) |
O3A—C1A—C2A | 124.5 (2) | O3B—C1B—C2B | 123.9 (2) |
O4A—C1A—C2A | 110.9 (2) | O4B—C1B—C2B | 111.1 (2) |
N19A—C2A—C1A | 108.2 (1) | N19B—C2B—C1B | 107.9 (1) |
N19A—C2A—C3A | 113.2 (1) | N19B—C2B—C3B | 112.3 (1) |
C1A—C2A—C3A | 114.8 (1) | C1B—C2B—C3B | 115.3 (1) |
C2A—C3A—C4A | 110.1 (1) | C2B—C3B—C4B | 109.1 (1) |
C2A—C3A—C5A | 110.5 (1) | C2B—C3B—C5B | 110.9 (1) |
C4A—C3A—C5A | 107.4 (1) | C4B—C3B—C5B | 107.9 (1) |
O1A—C4A—O2A | 124.4 (1) | O1B—C4B—O2B | 123.2 (2) |
O1A—C4A—C3A | 111.7 (1) | O1B—C4B—C3B | 111.7 (1) |
O2A—C4A—C3A | 123.8 (1) | O2B—C4B—C3B | 125.1 (2) |
C3A—C5A—C6A | 113.2 (1) | C3B—C5B—C6B | 113.6 (1) |
C5A—C6A—C7A | 121.3 (1) | C5B—C6B—C7B | 121.2 (2) |
C5A—C6A—C11A | 120.7 (2) | C5B—C6B—C11B | 120.7 (2) |
C7A—C6A—C11A | 118.0 (1) | C7B—C6B—C11B | 118.1 (2) |
C6A—C7A—C8A | 121.7 (1) | C6B—C7B—C8B | 120.6 (2) |
C7A—C8A—C9A | 119.4 (2) | C7B—C8B—C9B | 121.4 (2) |
C8A—C9A—C10A | 119.3 (2) | C8B—C9B—C10B | 119.1 (2) |
C9A—C10A—C11A | 120.9 (1) | C9B—C10B—C11B | 120.3 (2) |
C6A—C11A—C10A | 120.7 (2) | C6B—C11B—C10B | 120.5 (2) |
O5A—C12A—N19A | 125.9 (2) | O5B—C12B—N19B | 125.3 (2) |
O5A—C12A—C13A | 126.8 (2) | O5B—C12B—C13B | 127.3 (2) |
N19A—C12A—C13A | 107.3 (1) | N19B—C12B—C13B | 107.5 (1) |
N18A—C13A—C12A | 101.0 (1) | N18B—C13B—C12B | 101.4 (1) |
N18A—C13A—C15A | 114.2 (2) | N18B—C13B—C15B | 113.9 (1) |
C12A—C13A—C15A | 112.8 (1) | C12B—C13B—C15B | 112.5 (1) |
O6A—C14A—N18A | 129.7 (1) | O6B—C14B—N18B | 129.9 (2) |
O6A—C14A—N19A | 122.9 (2) | O6B—C14B—N19B | 123.0 (1) |
N18A—C14A—N19A | 107.4 (1) | N18B—C14B—N19B | 107.1 (1) |
C17A—O1A—C4A—O2A | 0.1 (2) | C17B—O1B—C4B—O2B | 1.3 (2) |
C17A—O1A—C4A—C3A | −176.7 (2) | C17B—O1B—C4B—C3B | 178.6 (2) |
C16A—O4A—C1A—O3A | 1.2 (2) | C16B—O4B—C1B—O3B | −0.3 (2) |
C16A—O4A—C1A—C2A | −178.6 (2) | C16B—O4B—C1B—C2B | 178.6 (2) |
C13A—N18A—C14A—O6A | −178.0 (2) | C13B—N18B—C14B—O6B | −178.7 (2) |
C13A—N18A—C14A—N19A | 2.7 (1) | C13B—N18B—C14B—N19B | 3.1 (1) |
C14A—N18A—C13A—C12A | −3.2 (1) | C14B—N18B—C13B—C12B | −2.4 (1) |
C14A—N18A—C13A—C15A | −124.6 (2) | C14B—N18B—C13B—C15B | −123.4 (2) |
C2A—N19A—C12A—O5A | 7.3 (2) | C2B—N19B—C12B—O5B | −8.9 (2) |
C12A—N19A—C2A—C1A | 68.2 (2) | C12B—N19B—C2B—C1B | −57.0 (2) |
C12A—N19A—C2A—C3A | −60.2 (2) | C12B—N19B—C2B—C3B | 71.2 (2) |
C2A—N19A—C12A—C13A | −171.3 (2) | C2B—N19B—C12B—C13B | 171.7 (2) |
C2A—N19A—C14A—O6A | −9.9 (2) | C2B—N19B—C14B—O6B | 8.3 (1) |
C2A—N19A—C14A—N18A | 169.6 (2) | C2B—N19B—C14B—N18B | −173.3 (2) |
C14A—N19A—C2A—C1A | −100.8 (2) | C14B—N19B—C2B—C1B | 112.4 (2) |
C14A—N19A—C2A—C3A | 130.8 (2) | C14B—N19B—C2B—C3B | −119.4 (2) |
C14A—N19A—C12A—O5A | 177.3 (2) | C14B—N19B—C12B—O5B | −179.5 (2) |
C12A—N19A—C14A—O6A | 179.8 (2) | C12B—N19B—C14B—O6B | 179.1 (2) |
C12A—N19A—C14A—N18A | −0.8 (1) | C12B—N19B—C14B—N18B | −2.5 (1) |
C14A—N19A—C12A—C13A | −1.3 (1) | C14B—N19B—C12B—C13B | 1.0 (1) |
O3A—C1A—C2A—N19A | 13.2 (2) | O3B—C1B—C2B—N19B | −26.1 (2) |
O3A—C1A—C2A—C3A | 140.7 (2) | O3B—C1B—C2B—C3B | −152.5 (2) |
O4A—C1A—C2A—N19A | −167.0 (2) | O4B—C1B—C2B—N19B | 155.0 (2) |
O4A—C1A—C2A—C3A | −39.5 (2) | O4B—C1B—C2B—C3B | 28.6 (1) |
N19A—C2A—C3A—C4A | −166.9 (2) | N19B—C2B—C3B—C4B | 170.2 (2) |
N19A—C2A—C3A—C5A | −48.4 (1) | N19B—C2B—C3B—C5B | 51.4 (1) |
C1A—C2A—C3A—C4A | 68.2 (2) | C1B—C2B—C3B—C4B | −65.6 (2) |
C1A—C2A—C3A—C5A | −173.3 (2) | C1B—C2B—C3B—C5B | 175.6 (2) |
C2A—C3A—C4A—O1A | −129.6 (2) | C2B—C3B—C4B—O1B | 133.2 (2) |
C2A—C3A—C4A—O2A | 53.7 (2) | C2B—C3B—C4B—O2B | −49.6 (2) |
C2A—C3A—C5A—C6A | 179.4 (2) | C2B—C3B—C5B—C6B | 178.4 (2) |
C5A—C3A—C4A—O1A | 110.1 (2) | C5B—C3B—C4B—O1B | −106.2 (2) |
C5A—C3A—C4A—O2A | −66.7 (2) | C5B—C3B—C4B—O2B | 71.0 (2) |
C4A—C3A—C5A—C6A | −60.5 (1) | C4B—C3B—C5B—C6B | 58.9 (2) |
C3A—C5A—C6A—C7A | 92.5 (2) | C3B—C5B—C6B—C7B | −90.8 (2) |
C3A—C5A—C6A—C11A | −86.0 (2) | C3B—C5B—C6B—C11B | 88.5 (2) |
C5A—C6A—C7A—C8A | −177.3 (2) | C5B—C6B—C7B—C8B | 179.6 (2) |
C5A—C6A—C11A—C10A | 177.5 (2) | C5B—C6B—C11B—C10B | −178.8 (2) |
C11A—C6A—C7A—C8A | 1.3 (2) | C11B—C6B—C7B—C8B | 0.3 (2) |
C7A—C6A—C11A—C10A | −1.1 (2) | C7B—C6B—C11B—C10B | 0.5 (2) |
C6A—C7A—C8A—C9A | −1.1 (2) | C6B—C7B—C8B—C9B | −1.2 (2) |
C7A—C8A—C9A—C10A | 0.7 (2) | C7B—C8B—C9B—C10B | 1.3 (2) |
C8A—C9A—C10A—C11A | −0.4 (2) | C8B—C9B—C10B—C11B | −0.4 (2) |
C9A—C10A—C11A—C6A | 0.6 (2) | C9B—C10B—C11B—C6B | −0.4 (2) |
O5A—C12A—C13A—N18A | −176.0 (2) | O5B—C12B—C13B—N18B | −178.7 (2) |
O5A—C12A—C13A—C15A | −53.7 (2) | O5B—C12B—C13B—C15B | −56.7 (2) |
N19A—C12A—C13A—N18A | 2.6 (1) | N19B—C12B—C13B—N18B | 0.7 (1) |
N19A—C12A—C13A—C15A | 124.9 (2) | N19B—C12B—C13B—C15B | 122.7 (2) |
Experimental details
Crystal data | |
Chemical formula | C17H20N2O6 |
Mr | 348.36 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 11.0323 (7), 11.7742 (4), 14.1121 (9) |
β (°) | 99.380 (2) |
V (Å3) | 1808.6 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.32 × 0.27 × 0.10 |
Data collection | |
Diffractometer | KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2.5σ(I)] reflections | 11340, 3708, 3033 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.623 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.048, 1.22 |
No. of reflections | 3033 |
No. of parameters | 374 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.16 |
Computer programs: KappaCCD software, DENZO and SCALEPAK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), maXus (Mackay et al., 1999), ORTEPII (Johnson, 1976).
N19A—C2A | 1.445 (1) | C1B—C2B | 1.524 (1) |
C1A—C2A | 1.533 (2) | C2B—C3B | 1.531 (1) |
C2A—C3A | 1.532 (1) | C3B—C4B | 1.501 (1) |
C3A—C4A | 1.509 (1) | C3B—C5B | 1.548 (1) |
C3A—C5A | 1.547 (1) | C5B—C6B | 1.507 (1) |
C5A—C6A | 1.502 (1) | C6B—C7B | 1.385 (2) |
N19B—C2B | 1.453 (1) | ||
N19A—C2A—C1A | 108.2 (1) | N19B—C2B—C1B | 107.9 (1) |
N19A—C2A—C3A | 113.2 (1) | N19B—C2B—C3B | 112.3 (1) |
C1A—C2A—C3A | 114.8 (1) | C1B—C2B—C3B | 115.3 (1) |
C2A—C3A—C4A | 110.1 (1) | C2B—C3B—C4B | 109.1 (1) |
C2A—C3A—C5A | 110.5 (1) | C2B—C3B—C5B | 110.9 (1) |
C4A—C3A—C5A | 107.4 (1) | C4B—C3B—C5B | 107.9 (1) |
C12A—N19A—C2A—C3A | −60.2 (2) | C12B—N19B—C2B—C3B | 71.2 (2) |
N19A—C2A—C3A—C4A | −166.9 (2) | N19B—C2B—C3B—C4B | 170.2 (2) |
N19A—C2A—C3A—C5A | −48.4 (1) | N19B—C2B—C3B—C5B | 51.4 (1) |
C1A—C2A—C3A—C4A | 68.2 (2) | C1B—C2B—C3B—C4B | −65.6 (2) |
C1A—C2A—C3A—C5A | −173.3 (2) | C1B—C2B—C3B—C5B | 175.6 (2) |
N19A—C12A—C13A—C15A | 124.9 (2) | N19B—C12B—C13B—C15B | 122.7 (2) |
Dans le cadre de nos travaux concernant la synthèse de cyclopeptides (El Mahdi et al., 1997, 2000), nous avons étudié la cyclization d'un précurseur peptidique linéaire, (I), en présence de benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) comme agent de couplage et de diisopropylethylamine (DIEA) comme base (Castro et al., 1976). L'analyse spectrale par RMN 1H (400 MHz) nous a permis déterminer que la structure du composé obtenu n'était pas celle du cyclopeptide attendu. Pour d'éterminer la nature de ce composé ainsi que sa stéréochimie, une analyse cristallographique a été réalisée par diffraction des rayons X. La structure cristalline d'un monocristal du composé (II) a conduit à une imidazoline-2,5-dione N-substituée sous forme de deux diastéréoisomères les composés (IIA) et (IIB) de configuration S,S,S et S,R,R. L'obtention du cycle imidazolidine s'explique par un réarrangement transannulaire du cyclopeptide à sept chaînons, accompagnée d'une migration du groupe benzyle (Jenhi et al., 2000). Les structures des composés (IIA) et (IIB) sont présents sous la forme d'un dimère constitué de deux molécules indépendantes. Les molécules (IIA) et (IIB) sont représentées sur la Fig. 1. Pour les deux composés la configuration absolue des carbones C2A, C3A, C2B et C3B établie à partir de la configuration connue S des carbones C13A et C13B provenant du résidu de la L-alanine. Ils sont de configuration R pour C2A et C3A et S pour C2B et C3B. On notera de ce fait l'inversion de signe des angles de torsion qui rendent compte de ces configurations pour (IIA) et (IIB) (Tableau 1). Exception faite de la configuration des carbones C2A et C3B pour (IIA) et C2A et C3B pour (IIB) les deux molécules (IIA) et (IIB) ont des géométries comparables. Les deux cycles imidazolidine C12A—C13A—N18A—C14A—N19A (déviation r.c.m. 0.031 Å) et C12B—C13B—N18B—C14B—N19B (déviation r.c.m. 0.033 Å) sont plans. Les angles de torsion C12A—N19A—C2A—C3A et C12B—N19B—C2B—C3B qui sont respectivement de 60.2 (2)° et -71.2 (2)° móntrent que ces deux plans n'ont pas la même orientation dans (IIA) et (IIB). les cycles aromatiques des phényles constitués des atomes C6A—C7A—C8A—C9A—C10A—C11A et C6A—C7A—C8A—C9A—C10A—C11A sont approximativement dans le même plan avec un angle entre les deux plans moyen de 2.8 (3)°. Les angles entre les deux plans moyen des hétérocycles et des benzyles sont respectivement de 55.1 (3) e t 44.2 (3)° pour (IIA) et (IIB).