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There are two symmetry-independent formula units of the title compound, dimethyl 3-benzyl-2-(4-methyl-2,5-di­oxo­imid­azol­idin-1-yl)­butane­dioate, C17H20N2O6, per cell. The two symmetry-independent molecules differ in their configuration and are diastereomers. This structural study confirms a new side reaction during the synthesis of seven-membered cyclopeptides. The stereochemistry of both diastereomers has been established.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100010830/gs1100sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010830/gs1100IIsup2.hkl
Contains datablock II

CCDC reference: 158249

Comment top

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).

Experimental top

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.

Refinement top

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].

Computing details top

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).

Figures top
[Figure 1] Fig. 1. Une vue ORTEPII (Johnson, 1976) de la structure moléculaire de (IIA) et (IIB) montrant la numérotation utilisé. Les ellipsoïdes de déplacement thermiques sont tracées au niveau de probabilité de 30% et les atomes d'hydrogènes sont représenté sous formes de spheres avec un rayon de 0.1 Å.
Dimethyl 3-benzyl-2-(4-methyl-2,5-dioxoimidazolidin-1-yl)butanedioate top
Crystal data top
C17H20N2O6F(000) = 736
Mr = 348.36Dx = 1.279 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 11.0323 (7) ÅCell parameters from 12894 reflections
b = 11.7742 (4) Åθ = 1.0–26.3°
c = 14.1121 (9) ŵ = 0.10 mm1
β = 99.380 (2)°T = 298 K
V = 1808.6 (2) Å3Prism, colourless'
Z = 40.32 × 0.27 × 0.10 mm
Data collection top
KappaCCD
diffractometer
Rint = 0.055
Radiation source: X-ray tubeθmax = 26.3°
ϕ scanh = 1313
11340 measured reflectionsk = 1213
3708 independent reflectionsl = 1617
3033 reflections with I > 2.5σ(I)
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.048 w = 1/[s2(Fo2) + 0.03Fo2]
S = 1.22(Δ/σ)max = 0.004
3033 reflectionsΔρmax = 0.17 e Å3
374 parametersΔρmin = 0.16 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C17H20N2O6V = 1808.6 (2) Å3
Mr = 348.36Z = 4
Monoclinic, P21Mo Kα radiation
a = 11.0323 (7) ŵ = 0.10 mm1
b = 11.7742 (4) ÅT = 298 K
c = 14.1121 (9) Å0.32 × 0.27 × 0.10 mm
β = 99.380 (2)°
Data collection top
KappaCCD
diffractometer
3033 reflections with I > 2.5σ(I)
11340 measured reflectionsRint = 0.055
3708 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.052374 parameters
wR(F2) = 0.048H-atom parameters constrained
S = 1.22Δρmax = 0.17 e Å3
3033 reflectionsΔρmin = 0.16 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.33898 (7)0.5013 (2)0.25187 (5)0.0595 (5)
O2A0.17861 (7)0.55186 (9)0.32227 (5)0.0557 (4)
O3A0.4065 (1)0.8948 (1)0.35387 (8)0.1398 (8)
O4A0.41121 (7)0.7107 (1)0.37530 (5)0.0713 (5)
O5A0.35876 (9)0.8829 (1)0.11625 (7)0.1178 (7)
O6A0.05453 (7)0.94169 (9)0.29109 (5)0.0626 (5)
N18A0.12957 (8)1.0542 (1)0.18050 (6)0.0571 (5)
N19A0.21122 (8)0.88505 (9)0.21295 (6)0.0505 (5)
C1A0.3637 (1)0.8058 (1)0.33741 (8)0.0619 (7)
C2A0.24380 (9)0.7832 (1)0.26848 (7)0.0450 (5)
C3A0.24478 (9)0.6766 (1)0.20630 (6)0.0407 (5)
C4A0.2500 (1)0.5716 (1)0.26819 (7)0.0426 (6)
C5A0.1258 (1)0.6695 (1)0.13152 (7)0.0525 (6)
C6A0.12154 (9)0.5672 (1)0.06741 (6)0.0449 (6)
C7A0.06794 (9)0.4676 (1)0.08968 (7)0.0559 (7)
C8A0.0680 (1)0.3709 (1)0.03286 (7)0.0594 (7)
C9A0.1211 (1)0.3754 (1)0.04823 (7)0.0586 (7)
C10A0.1746 (1)0.4754 (1)0.07171 (7)0.0603 (7)
C11A0.1745 (1)0.5699 (1)0.01526 (7)0.0516 (6)
C12A0.2746 (1)0.9282 (1)0.14554 (8)0.0698 (7)
C13A0.2206 (1)1.0439 (1)0.11681 (8)0.0663 (7)
C14A0.12206 (9)0.9618 (1)0.23371 (7)0.0463 (6)
C15A0.3147 (1)1.1355 (1)0.1286 (1)0.1067 (9)
C16A0.5249 (1)0.7200 (2)0.44449 (9)0.101 (1)
C17A0.3440 (1)0.3957 (1)0.3052 (1)0.103 (1)
O1B0.65409 (7)0.65575 (6)0.24134 (5)0.0643 (5)
O2B0.80389 (7)0.6068 (1)0.16013 (5)0.0705 (5)
O3B0.59637 (8)0.2651 (1)0.10461 (6)0.0871 (6)
O4B0.57374 (7)0.4529 (1)0.11556 (5)0.0659 (5)
O5B0.60220 (7)0.2526 (1)0.33151 (6)0.0887 (5)
O6B0.95963 (7)0.23090 (9)0.21082 (5)0.0573 (4)
N18B0.86741 (8)0.1071 (1)0.30372 (6)0.0567 (5)
N19B0.77533 (7)0.26960 (9)0.26239 (5)0.0460 (5)
C1B0.6303 (1)0.3569 (1)0.13773 (8)0.0563 (7)
C2B0.7476 (1)0.3750 (1)0.20979 (6)0.0451 (6)
C3B0.74609 (9)0.4773 (1)0.27654 (6)0.0436 (6)
C4B0.7389 (1)0.5843 (1)0.21816 (7)0.0499 (6)
C5B0.8652 (1)0.4822 (1)0.35164 (7)0.0584 (7)
C6B0.8710 (1)0.5830 (1)0.41788 (7)0.0526 (6)
C7B0.9237 (1)0.6845 (1)0.39594 (8)0.0639 (7)
C8B0.9276 (1)0.7759 (1)0.45667 (9)0.0724 (8)
C9B0.8785 (1)0.7706 (1)0.53949 (8)0.0682 (8)
C10B0.8263 (1)0.6715 (1)0.56267 (8)0.0693 (8)
C11B0.8226 (1)0.5769 (1)0.50213 (8)0.0645 (7)
C12B0.6978 (1)0.2149 (1)0.31381 (7)0.0586 (6)
C13B0.7543 (1)0.1019 (1)0.34394 (7)0.0568 (6)
C14B0.8782 (1)0.2012 (1)0.25436 (7)0.0463 (6)
C15B0.7741 (1)0.0857 (1)0.45088 (8)0.0911 (9)
C16B0.4618 (1)0.4499 (1)0.04577 (8)0.0742 (8)
C17B0.6411 (2)0.7628 (2)0.1912 (1)0.121 (1)
H2A0.1823420.7676320.3076730.065032*
H3A0.3145030.6784360.1735470.059079*
H5A10.1210080.7372950.0932320.071957*
H5A20.0577520.6671810.1660320.071957*
H7A0.0292320.4656110.1458540.076515*
H8A0.0317780.3014800.0504040.078979*
H9A0.1211710.3099280.0888070.076866*
H10A0.2120690.4780910.1284580.078865*
H11A0.2112490.6391490.0326910.071694*
H13A0.1801871.0468870.0512330.086387*
H15A10.2762181.2069130.1095390.126568*
H15A20.3753491.1188960.0889730.126568*
H15A30.3534101.1397530.1945820.126568*
H16A10.5506340.6456290.4673100.115766*
H16A20.5111550.7664560.4976470.115766*
H16A30.5875590.7537760.4138080.115766*
H17A10.4106370.3501230.2904130.124271*
H17A20.2680060.3556350.2869820.124271*
H17A30.3562060.4110220.3729020.124271*
H18A0.0776761.1185170.1860650.076786*
H2B0.8115870.3916520.1732240.064361*
H3B0.6763500.4718700.3090500.063546*
H5BA0.9332270.4845540.3170660.076473*
H5BB0.8689400.4134680.3886530.076473*
H7B0.9577710.6903430.3377370.082441*
H8B0.9656380.8447300.4397850.091550*
H9B0.8807810.8353900.5810130.086752*
H10B0.7917020.6668930.6207400.088845*
H11B0.7861540.5072780.5189310.082101*
H13B0.7051690.0391840.3163750.075802*
H15B10.8101330.0125470.4667410.110110*
H15B20.6966920.0906140.4733310.110110*
H15B30.8281660.1438720.4809600.110110*
H16B10.4287360.5252000.0356440.097248*
H16B20.4028480.4018520.0691040.097248*
H16B30.4797290.4202490.0137770.097248*
H17B10.5786360.8073240.2137270.155445*
H17B20.6179670.7489730.1236040.155445*
H17B30.7176220.8032580.2024930.155445*
H18B0.9306100.0503580.3091680.070012*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0625 (5)0.0456 (5)0.0705 (5)0.0262 (4)0.0231 (4)0.0118 (4)
O2A0.0549 (5)0.0561 (5)0.0567 (4)0.0112 (4)0.0211 (4)0.0055 (4)
O3A0.1211 (9)0.0672 (7)0.211 (1)0.0242 (6)0.0665 (8)0.0154 (7)
O4A0.0590 (5)0.0744 (7)0.0739 (5)0.0091 (5)0.0182 (4)0.0033 (5)
O5A0.1083 (7)0.0745 (6)0.1799 (9)0.0392 (6)0.1028 (7)0.0396 (6)
O6A0.0635 (5)0.0544 (5)0.0724 (5)0.0180 (4)0.0351 (4)0.0059 (4)
N18A0.0566 (6)0.0385 (6)0.0760 (6)0.0116 (5)0.0252 (5)0.0061 (5)
N19A0.0514 (5)0.0353 (5)0.0652 (5)0.0123 (4)0.0236 (4)0.0025 (4)
C1A0.0579 (7)0.0550 (8)0.0705 (8)0.0031 (7)0.0103 (6)0.0164 (6)
C2A0.0368 (6)0.0477 (7)0.0500 (6)0.0095 (5)0.0113 (5)0.0025 (5)
C3A0.0408 (6)0.0365 (6)0.0438 (5)0.0065 (5)0.0085 (4)0.0027 (4)
C4A0.0409 (5)0.0406 (7)0.0445 (5)0.0103 (5)0.0020 (5)0.0050 (5)
C5A0.0445 (6)0.0580 (8)0.0520 (6)0.0146 (6)0.0024 (5)0.0008 (5)
C6A0.0397 (6)0.0479 (7)0.0440 (6)0.0096 (5)0.0042 (5)0.0008 (5)
C7A0.0475 (7)0.0673 (9)0.0511 (6)0.0085 (6)0.0098 (5)0.0049 (6)
C8A0.0622 (8)0.0515 (8)0.0625 (7)0.0076 (6)0.0070 (6)0.0110 (6)
C9A0.0558 (7)0.0605 (8)0.0565 (7)0.0021 (6)0.0005 (5)0.0121 (6)
C10A0.0584 (7)0.0752 (9)0.0465 (6)0.0016 (7)0.0087 (5)0.0022 (6)
C11A0.0506 (7)0.0559 (8)0.0470 (6)0.0030 (6)0.0046 (5)0.0064 (5)
C12A0.0633 (7)0.0505 (7)0.0985 (9)0.0123 (6)0.0426 (7)0.0114 (6)
C13A0.0608 (7)0.0510 (8)0.0885 (8)0.0117 (6)0.0293 (6)0.0091 (6)
C14A0.0451 (5)0.0406 (7)0.0526 (6)0.0083 (5)0.0134 (5)0.0057 (5)
C15A0.0718 (8)0.0555 (8)0.194 (1)0.0012 (6)0.0518 (9)0.0262 (8)
C16A0.0592 (8)0.164 (2)0.0754 (8)0.0092 (9)0.0198 (7)0.0146 (9)
C17A0.114 (1)0.065 (1)0.130 (1)0.0571 (9)0.0412 (9)0.0273 (9)
O1B0.0586 (5)0.0515 (5)0.0840 (5)0.0237 (4)0.0306 (4)0.0193 (4)
O2B0.0606 (5)0.0642 (6)0.0883 (5)0.0153 (4)0.0355 (4)0.0204 (4)
O3B0.0908 (6)0.0631 (6)0.1006 (6)0.0042 (5)0.0103 (5)0.0077 (5)
O4B0.0518 (5)0.0749 (6)0.0660 (5)0.0258 (5)0.0109 (4)0.0106 (4)
O5B0.0577 (5)0.0849 (6)0.1272 (7)0.0329 (4)0.0492 (5)0.0459 (5)
O6B0.0544 (4)0.0469 (4)0.0717 (4)0.0142 (4)0.0318 (4)0.0084 (3)
N18B0.0541 (6)0.0483 (6)0.0673 (6)0.0203 (5)0.0254 (4)0.0124 (5)
N19B0.0421 (9)0.0368 (5)0.0600 (5)0.0089 (4)0.0179 (4)0.0097 (4)
C1B0.0463 (9)0.0619 (8)0.0595 (7)0.0017 (6)0.0126 (5)0.0045 (6)
C2B0.0452 (6)0.0379 (6)0.0511 (6)0.0086 (5)0.0109 (5)0.0093 (5)
C3B0.0347 (6)0.0487 (7)0.0462 (6)0.0116 (5)0.0074 (4)0.0065 (5)
C4B0.0404 (9)0.0443 (7)0.0639 (7)0.0092 (5)0.0138 (5)0.0073 (5)
C5B0.0555 (7)0.0509 (8)0.0650 (7)0.0129 (6)0.0018 (5)0.0005 (6)
C6B0.0428 (6)0.0573 (8)0.0549 (7)0.0093 (6)0.0010 (5)0.0005 (6)
C7B0.0583 (8)0.0663 (9)0.0668 (7)0.0038 (7)0.0166 (6)0.0037 (7)
C8B0.0650 (9)0.0665 (9)0.0843 (9)0.0137 (7)0.0141 (7)0.0048 (7)
C9B0.0640 (8)0.0672 (9)0.0698 (8)0.0061 (7)0.0007 (6)0.0114 (7)
C10B0.0745 (9)0.078 (1)0.0531 (7)0.0022 (8)0.0045 (6)0.0034 (7)
C11B0.0698 (8)0.0621 (8)0.0565 (7)0.0007 (7)0.0082 (6)0.0087 (6)
C12B0.0526 (9)0.0530 (7)0.0699 (7)0.0137 (5)0.0198 (5)0.0136 (5)
C13B0.0600 (7)0.0486 (7)0.0635 (7)0.0101 (5)0.0254 (5)0.0132 (5)
C14B0.0463 (9)0.0379 (7)0.0530 (6)0.0095 (5)0.0070 (5)0.0033 (5)
C15B0.108 (1)0.090 (1)0.0761 (8)0.0465 (8)0.0380 (7)0.0302 (7)
C16B0.0539 (7)0.099 (1)0.0647 (7)0.0171 (7)0.0087 (6)0.0044 (7)
C17B0.125 (1)0.072 (1)0.173 (1)0.051 (1)0.082 (1)0.065 (1)
Geometric parameters (Å, º) top
O1A—C4A1.332 (1)O1B—C4B1.338 (1)
O1A—C17A1.447 (1)O1B—C17B1.441 (2)
O2A—C4A1.206 (1)O2B—C4B1.203 (1)
O3A—C1A1.157 (2)O3B—C1B1.212 (1)
O4A—C1A1.312 (1)O4B—C1B1.305 (1)
O4A—C16A1.462 (1)O4B—C16B1.448 (1)
O5A—C12A1.200 (1)O5B—C12B1.208 (1)
O6A—C14A1.209 (1)O6B—C14B1.219 (1)
N18A—C13A1.457 (1)N18B—C13B1.454 (1)
N18A—C14A1.333 (1)N18B—C14B1.326 (1)
N19A—C2A1.445 (1)N19B—C2B1.453 (1)
N19A—C12A1.367 (1)N19B—C12B1.370 (1)
N19A—C14A1.402 (1)N19B—C14B1.411 (1)
C1A—C2A1.533 (2)C1B—C2B1.524 (1)
C2A—C3A1.532 (1)C2B—C3B1.531 (1)
C3A—C4A1.509 (1)C3B—C4B1.501 (1)
C3A—C5A1.547 (1)C3B—C5B1.548 (1)
C5A—C6A1.502 (1)C5B—C6B1.507 (1)
C6A—C7A1.373 (1)C6B—C7B1.385 (2)
C6A—C11A1.388 (1)C6B—C11B1.382 (2)
C7A—C8A1.392 (2)C7B—C8B1.373 (2)
C8A—C9A1.369 (1)C8B—C9B1.366 (2)
C9A—C10A1.381 (2)C9B—C10B1.364 (2)
C10A—C11A1.369 (2)C10B—C11B1.401 (2)
C12A—C13A1.515 (2)C12B—C13B1.500 (2)
C13A—C15A1.485 (2)C13B—C15B1.501 (1)
C4A—O1A—C17A114.2 (1)C4B—O1B—C17B116.6 (1)
C1A—O4A—C16A116.8 (2)C1B—O4B—C16B117.5 (1)
C13A—N18A—C14A113.0 (1)C13B—N18B—C14B113.3 (1)
C2A—N19A—C12A125.2 (1)C2B—N19B—C12B125.1 (1)
C2A—N19A—C14A122.9 (1)C2B—N19B—C14B123.5 (1)
C12A—N19A—C14A111.2 (1)C12B—N19B—C14B110.7 (1)
O3A—C1A—O4A124.6 (2)O3B—C1B—O4B125.0 (2)
O3A—C1A—C2A124.5 (2)O3B—C1B—C2B123.9 (2)
O4A—C1A—C2A110.9 (2)O4B—C1B—C2B111.1 (2)
N19A—C2A—C1A108.2 (1)N19B—C2B—C1B107.9 (1)
N19A—C2A—C3A113.2 (1)N19B—C2B—C3B112.3 (1)
C1A—C2A—C3A114.8 (1)C1B—C2B—C3B115.3 (1)
C2A—C3A—C4A110.1 (1)C2B—C3B—C4B109.1 (1)
C2A—C3A—C5A110.5 (1)C2B—C3B—C5B110.9 (1)
C4A—C3A—C5A107.4 (1)C4B—C3B—C5B107.9 (1)
O1A—C4A—O2A124.4 (1)O1B—C4B—O2B123.2 (2)
O1A—C4A—C3A111.7 (1)O1B—C4B—C3B111.7 (1)
O2A—C4A—C3A123.8 (1)O2B—C4B—C3B125.1 (2)
C3A—C5A—C6A113.2 (1)C3B—C5B—C6B113.6 (1)
C5A—C6A—C7A121.3 (1)C5B—C6B—C7B121.2 (2)
C5A—C6A—C11A120.7 (2)C5B—C6B—C11B120.7 (2)
C7A—C6A—C11A118.0 (1)C7B—C6B—C11B118.1 (2)
C6A—C7A—C8A121.7 (1)C6B—C7B—C8B120.6 (2)
C7A—C8A—C9A119.4 (2)C7B—C8B—C9B121.4 (2)
C8A—C9A—C10A119.3 (2)C8B—C9B—C10B119.1 (2)
C9A—C10A—C11A120.9 (1)C9B—C10B—C11B120.3 (2)
C6A—C11A—C10A120.7 (2)C6B—C11B—C10B120.5 (2)
O5A—C12A—N19A125.9 (2)O5B—C12B—N19B125.3 (2)
O5A—C12A—C13A126.8 (2)O5B—C12B—C13B127.3 (2)
N19A—C12A—C13A107.3 (1)N19B—C12B—C13B107.5 (1)
N18A—C13A—C12A101.0 (1)N18B—C13B—C12B101.4 (1)
N18A—C13A—C15A114.2 (2)N18B—C13B—C15B113.9 (1)
C12A—C13A—C15A112.8 (1)C12B—C13B—C15B112.5 (1)
O6A—C14A—N18A129.7 (1)O6B—C14B—N18B129.9 (2)
O6A—C14A—N19A122.9 (2)O6B—C14B—N19B123.0 (1)
N18A—C14A—N19A107.4 (1)N18B—C14B—N19B107.1 (1)
C17A—O1A—C4A—O2A0.1 (2)C17B—O1B—C4B—O2B1.3 (2)
C17A—O1A—C4A—C3A176.7 (2)C17B—O1B—C4B—C3B178.6 (2)
C16A—O4A—C1A—O3A1.2 (2)C16B—O4B—C1B—O3B0.3 (2)
C16A—O4A—C1A—C2A178.6 (2)C16B—O4B—C1B—C2B178.6 (2)
C13A—N18A—C14A—O6A178.0 (2)C13B—N18B—C14B—O6B178.7 (2)
C13A—N18A—C14A—N19A2.7 (1)C13B—N18B—C14B—N19B3.1 (1)
C14A—N18A—C13A—C12A3.2 (1)C14B—N18B—C13B—C12B2.4 (1)
C14A—N18A—C13A—C15A124.6 (2)C14B—N18B—C13B—C15B123.4 (2)
C2A—N19A—C12A—O5A7.3 (2)C2B—N19B—C12B—O5B8.9 (2)
C12A—N19A—C2A—C1A68.2 (2)C12B—N19B—C2B—C1B57.0 (2)
C12A—N19A—C2A—C3A60.2 (2)C12B—N19B—C2B—C3B71.2 (2)
C2A—N19A—C12A—C13A171.3 (2)C2B—N19B—C12B—C13B171.7 (2)
C2A—N19A—C14A—O6A9.9 (2)C2B—N19B—C14B—O6B8.3 (1)
C2A—N19A—C14A—N18A169.6 (2)C2B—N19B—C14B—N18B173.3 (2)
C14A—N19A—C2A—C1A100.8 (2)C14B—N19B—C2B—C1B112.4 (2)
C14A—N19A—C2A—C3A130.8 (2)C14B—N19B—C2B—C3B119.4 (2)
C14A—N19A—C12A—O5A177.3 (2)C14B—N19B—C12B—O5B179.5 (2)
C12A—N19A—C14A—O6A179.8 (2)C12B—N19B—C14B—O6B179.1 (2)
C12A—N19A—C14A—N18A0.8 (1)C12B—N19B—C14B—N18B2.5 (1)
C14A—N19A—C12A—C13A1.3 (1)C14B—N19B—C12B—C13B1.0 (1)
O3A—C1A—C2A—N19A13.2 (2)O3B—C1B—C2B—N19B26.1 (2)
O3A—C1A—C2A—C3A140.7 (2)O3B—C1B—C2B—C3B152.5 (2)
O4A—C1A—C2A—N19A167.0 (2)O4B—C1B—C2B—N19B155.0 (2)
O4A—C1A—C2A—C3A39.5 (2)O4B—C1B—C2B—C3B28.6 (1)
N19A—C2A—C3A—C4A166.9 (2)N19B—C2B—C3B—C4B170.2 (2)
N19A—C2A—C3A—C5A48.4 (1)N19B—C2B—C3B—C5B51.4 (1)
C1A—C2A—C3A—C4A68.2 (2)C1B—C2B—C3B—C4B65.6 (2)
C1A—C2A—C3A—C5A173.3 (2)C1B—C2B—C3B—C5B175.6 (2)
C2A—C3A—C4A—O1A129.6 (2)C2B—C3B—C4B—O1B133.2 (2)
C2A—C3A—C4A—O2A53.7 (2)C2B—C3B—C4B—O2B49.6 (2)
C2A—C3A—C5A—C6A179.4 (2)C2B—C3B—C5B—C6B178.4 (2)
C5A—C3A—C4A—O1A110.1 (2)C5B—C3B—C4B—O1B106.2 (2)
C5A—C3A—C4A—O2A66.7 (2)C5B—C3B—C4B—O2B71.0 (2)
C4A—C3A—C5A—C6A60.5 (1)C4B—C3B—C5B—C6B58.9 (2)
C3A—C5A—C6A—C7A92.5 (2)C3B—C5B—C6B—C7B90.8 (2)
C3A—C5A—C6A—C11A86.0 (2)C3B—C5B—C6B—C11B88.5 (2)
C5A—C6A—C7A—C8A177.3 (2)C5B—C6B—C7B—C8B179.6 (2)
C5A—C6A—C11A—C10A177.5 (2)C5B—C6B—C11B—C10B178.8 (2)
C11A—C6A—C7A—C8A1.3 (2)C11B—C6B—C7B—C8B0.3 (2)
C7A—C6A—C11A—C10A1.1 (2)C7B—C6B—C11B—C10B0.5 (2)
C6A—C7A—C8A—C9A1.1 (2)C6B—C7B—C8B—C9B1.2 (2)
C7A—C8A—C9A—C10A0.7 (2)C7B—C8B—C9B—C10B1.3 (2)
C8A—C9A—C10A—C11A0.4 (2)C8B—C9B—C10B—C11B0.4 (2)
C9A—C10A—C11A—C6A0.6 (2)C9B—C10B—C11B—C6B0.4 (2)
O5A—C12A—C13A—N18A176.0 (2)O5B—C12B—C13B—N18B178.7 (2)
O5A—C12A—C13A—C15A53.7 (2)O5B—C12B—C13B—C15B56.7 (2)
N19A—C12A—C13A—N18A2.6 (1)N19B—C12B—C13B—N18B0.7 (1)
N19A—C12A—C13A—C15A124.9 (2)N19B—C12B—C13B—C15B122.7 (2)

Experimental details

Crystal data
Chemical formulaC17H20N2O6
Mr348.36
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)11.0323 (7), 11.7742 (4), 14.1121 (9)
β (°) 99.380 (2)
V3)1808.6 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.32 × 0.27 × 0.10
Data collection
DiffractometerKappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2.5σ(I)] reflections
11340, 3708, 3033
Rint0.055
(sin θ/λ)max1)0.623
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.048, 1.22
No. of reflections3033
No. of parameters374
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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).

Selected geometric parameters (Å, º) top
N19A—C2A1.445 (1)C1B—C2B1.524 (1)
C1A—C2A1.533 (2)C2B—C3B1.531 (1)
C2A—C3A1.532 (1)C3B—C4B1.501 (1)
C3A—C4A1.509 (1)C3B—C5B1.548 (1)
C3A—C5A1.547 (1)C5B—C6B1.507 (1)
C5A—C6A1.502 (1)C6B—C7B1.385 (2)
N19B—C2B1.453 (1)
N19A—C2A—C1A108.2 (1)N19B—C2B—C1B107.9 (1)
N19A—C2A—C3A113.2 (1)N19B—C2B—C3B112.3 (1)
C1A—C2A—C3A114.8 (1)C1B—C2B—C3B115.3 (1)
C2A—C3A—C4A110.1 (1)C2B—C3B—C4B109.1 (1)
C2A—C3A—C5A110.5 (1)C2B—C3B—C5B110.9 (1)
C4A—C3A—C5A107.4 (1)C4B—C3B—C5B107.9 (1)
C12A—N19A—C2A—C3A60.2 (2)C12B—N19B—C2B—C3B71.2 (2)
N19A—C2A—C3A—C4A166.9 (2)N19B—C2B—C3B—C4B170.2 (2)
N19A—C2A—C3A—C5A48.4 (1)N19B—C2B—C3B—C5B51.4 (1)
C1A—C2A—C3A—C4A68.2 (2)C1B—C2B—C3B—C4B65.6 (2)
C1A—C2A—C3A—C5A173.3 (2)C1B—C2B—C3B—C5B175.6 (2)
N19A—C12A—C13A—C15A124.9 (2)N19B—C12B—C13B—C15B122.7 (2)
 

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