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We present the crystal and molecular structures of two new N-phthalyl-3-amino-2-arylpropionic acid pantolactonyl ester derivatives with 4-fluorophenyl and 3,4-dimethoxyphenyl as the aryl group, 2,3,4,5-tetrahydro-4,4-dimethyl-2-oxofuran-3-yl 3-phthalimido-2-(4-fluorophenyl)propanoate, C23H20FNO6, and 2,3,4,5-tetrahydro-4,4-dimethyl-2-oxofuran-3-yl 3-phthalimido-2-(3,4-dimethoxyphenyl)propanoate ethyl acetate hemisolvate, C25H25NO8·0.5C4H8O2. This structural study confirms the S configuration of the C2 and validates the stereospecificity of our synthesis strategy.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199015292/gs1061sup1.cif
Contains datablocks global, II, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199015292/gs1061Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199015292/gs1061IIsup3.hkl
Contains datablock II

CCDC references: 136875; 144625; 144626

Comment top

Les β-amino acides et leurs dérivés forment une famille importante de composés pour le développement de pseudopeptides (Xie et al., 1989) et de β-lactames fonctionnalisés (Salzmann et al., 1980). Incorporés dans un peptide ou sous forme libre, ils présentent des activités biologiques intéressantes, (Juaristi, 1997). Dans le but d'extrapoler les résultats obtenus par notre équipe dans la série des acides 3-amino-2-arylpropanoïques (Calmès & Escale, 1998), nous décrivons ici la structure de deux nouveaux dérivés de cet acide. La synthèse des esters (R)-pantolactonyl des acides (S)—N-phtaloyl-3-amino-2-(4-fluorophényl)propanoïque, (I), (S)—N-phtaloyl-3-amino-2-(3,4-diméthoxyphényl)propanoïque, (II), et (S)—N-phtaloyl-3-amino-2-(4-méthoxyphényl)propanoïque, (III) (Calmès et al., 1999) a été réalisée en utilisant les mêmes méthodes que lors de la préparation de l'acide (S)-3-amino-2-phénylpropanoïque (Calmès & Escale, 1998). L'analyse spectrale par RMN 1H (400 MHz) ne nous permettant pas d'attribuer la stéréochimie du carbone C2, l'étude de ces trois composés a été effectuée par diffraction des rayons X. Nous présentons ici les structures des composés (I) et (II). \sch

Les molécules (I) et (II) sont représentées respectivement sur les Figures 1 e t 2. Ces structures montrent que pour les deux composés la configuration absolue du carbone α C2 établie à partir de la configuration connue R du carbone C19 de la pantolactone est dans tous les cas de configuration S. La structure du composé (III) donne la même configuration S pour le carbone C2, elle n'est pas décrite ici montrant peu de différence avec le composé (I). Pour les deux composés les deux cycles aromatiques, le phényle constitué des atomes C4—C5—C6—C7—C8—C9 et le N-phtalyle constitué des atomes N1—C10—C11—C12—C13—C14—C15—C16—C17 sont approximativement dans le même plan. Les angles entre les deux plans moyens sont respectivement de 8,5(4)° et 16,9(4)° pour les composés (I) et (II). L'angle plus important pour le produit (II) est dû à la présence d'une demi molécule d'acétate d'éthyle dans la maille. On notera que les angles de torsion C19—O1—C1—C2 sont similaires, 178,5(1)° pour (I) et -174,9(4)° pour (II). Seul l'angle de torsion O1—C1—C2—C3 varie de 162,5(4)° pour le produit (II) comparé à -142,1(1)° pour le produit (I). La variation majeure de géométrie entre les composés est une rotation autour de la liaison C1—C2. Les cycles pantolactoniques C18—C19—C20—C21—O6 sont dans des conformations enveloppe, le carbone C20 étant distant respectivement de 0,599 (1) e t 0,612 (3) Å du plan moyen formé par les atomes C18, C19, C21 et O6 des composés (I) et (II). L'atome C24 du substituant méthoxy de (II) est dans le même plan que le phényl qui le supporte.

Experimental top

Ces trois composés ont été synthetisés à partir des acides 3-amino-2-arylpropanoïques racémiques via l'addition diastéréoselective de la (R)-pantolactone à leurs cétènes. Cette réaction permet la préparation d'esters pantolactoniques énantiomériquement purs des acides (S)—N-Phtaloyl-3-amino-2-(4-fluorophényl, 4-méthoxyphényl et 3,4-dimethoxyphenyl)propanoïques. Les cristallizations des trois composés ont été effectuées à température ambiante à partir d'un mélange d'acétate d'éthyle et d'hexane.

Refinement top

Pour le composé (III), les listes des coordonnées des atomes, des facteurs d'agitation thermique anisotrope, des facteurs de structure et des distances et angles ont été déposées au dépôt d'archives de Cambridge Crystallographic Data Centre (Reference CCDC 136875). On peut en obtenir des copies en s'addressant a: CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk). Le composé (II) cristallize avec une demi molécule d'acétate d'éthyle (confirmé par 1H RMN des cristaux). Cette demi molécule de solvant a été rajoutée dans la formule brute, ce qui explique un désorde de 50%. Il n'a pas été possible d'assigner les hydrogènes de cette molécule de solvant.

Computing details top

For both compounds, data collection: KappaCCD Server Software (Nonius, 1997); data reduction: DENZO and SCALEPACK (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.

Figures top
[Figure 1] Fig. 1. Vue de (I). Les ellipsoïdes de déplacement sont tracées au niveau de probabilité de 50%.
[Figure 2] Fig. 2. Vue de (II). Les ellipsoïdes de déplacement sont tracées au niveau de probabilité de 50%. Pour une plus grande clarté, la demi molécule d'acétate d'éthyle n'est pas représentée.
(I) top
Crystal data top
C23H20FNO6Dx = 1.31 Mg m3
Mr = 425.41Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 14895 reflections
a = 9.5666 (3) Åθ = 1.0–25.4°
b = 11.1026 (2) ŵ = 0.1 mm1
c = 20.3200 (6) ÅT = 298 K
V = 2158.3 (2) Å3Prism, colorless
Z = 40.32 × 0.27 × 0.10 mm
Data collection top
KappaCCD
diffractometer
Rint = 0.028
phi–scanθmax = 25.4°
13240 measured reflectionsh = 1111
2362 independent reflectionsk = 1212
2209 reflections with refl_observed_if_I_ > _3.00_σ(I)l = 2425
Refinement top
Refinement on FH-atom parameters not refined
R[F2 > 2σ(F2)] = 0.033 w = 1/[σ2(F) + 0.03F2]
wR(F2) = 0.052(Δ/σ)max = 0.007
S = 1.22Δρmax = 0.10 e Å3
2209 reflectionsΔρmin = 0.10 e Å3
273 parameters
Crystal data top
C23H20FNO6V = 2158.3 (2) Å3
Mr = 425.41Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 9.5666 (3) ŵ = 0.1 mm1
b = 11.1026 (2) ÅT = 298 K
c = 20.3200 (6) Å0.32 × 0.27 × 0.10 mm
Data collection top
KappaCCD
diffractometer
2209 reflections with refl_observed_if_I_ > _3.00_σ(I)
13240 measured reflectionsRint = 0.028
2362 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.033273 parameters
wR(F2) = 0.052H-atom parameters not refined
S = 1.22Δρmax = 0.10 e Å3
2209 reflectionsΔρmin = 0.10 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.34540 (4)0.88610 (4)0.50450 (2)0.0941 (2)
O10.71590 (5)0.43500 (4)0.35980 (2)0.0480 (2)
O20.71550 (4)0.37200 (5)0.46500 (2)0.0522 (2)
O30.57870 (6)0.13430 (6)0.51940 (3)0.0494 (3)
O40.35670 (5)0.21880 (4)0.32620 (2)0.0684 (2)
O50.89860 (6)0.63200 (6)0.33060 (3)0.0913 (3)
O61.04710 (6)0.49290 (4)0.29440 (3)0.0787 (3)
N10.46280 (6)0.20720 (6)0.42760 (3)0.0380 (3)
C10.65380 (7)0.40690 (5)0.41750 (3)0.0375 (3)
C20.49750 (6)0.42570 (5)0.41350 (3)0.0396 (3)
C30.42230 (6)0.32550 (5)0.45200 (3)0.0430 (3)
C40.45700 (7)0.54950 (6)0.43880 (3)0.0432 (3)
C50.37050 (6)0.62290 (5)0.40170 (3)0.0567 (3)
C60.33230 (8)0.73670 (7)0.42400 (4)0.0694 (4)
C70.38160 (6)0.77430 (5)0.48320 (3)0.0644 (3)
C80.46590 (8)0.70540 (6)0.52170 (4)0.0639 (4)
C90.50380 (7)0.59170 (6)0.49890 (3)0.0535 (3)
C100.43020 (9)0.16530 (7)0.36500 (4)0.0445 (4)
C110.50340 (7)0.04880 (7)0.35750 (4)0.0479 (4)
C120.51490 (6)0.02830 (5)0.30430 (3)0.0678 (3)
C130.59790 (9)0.13030 (7)0.31310 (5)0.0818 (5)
C140.66450 (8)0.15370 (6)0.37110 (5)0.0773 (4)
C150.65290 (7)0.07730 (8)0.42400 (4)0.0593 (4)
C160.57170 (9)0.02440 (8)0.41590 (6)0.0427 (5)
C170.54290 (8)0.12360 (8)0.46270 (4)0.0378 (4)
C180.9323 (1)0.5288 (1)0.32720 (4)0.0595 (6)
C190.86400 (7)0.41830 (7)0.35630 (4)0.0426 (3)
C200.9103 (1)0.31630 (9)0.31100 (5)0.0491 (6)
C211.0581 (1)0.36220 (8)0.29660 (4)0.0682 (5)
C220.82430 (9)0.31310 (9)0.24830 (4)0.0839 (5)
C230.91320 (7)0.19420 (6)0.34460 (3)0.0738 (3)
H20.4701 (7)0.4180 (5)0.3682 (3)0.05930*
H3A0.3200 (7)0.3375 (6)0.4484 (3)0.06300*
H3B0.4492 (8)0.3307 (7)0.4984 (4)0.06300*
H50.3467 (6)0.5972 (5)0.3620 (4)0.07670*
H60.279 (1)0.7936 (8)0.3986 (5)0.08940*
H80.4944 (9)0.7311 (8)0.5640 (5)0.08390*
H90.5618 (9)0.5406 (8)0.5247 (4)0.07350*
H120.4672 (9)0.0080 (9)0.2671 (5)0.08780*
H130.602 (1)0.169 (1)0.2758 (6)0.10180*
H140.7211 (9)0.2283 (8)0.3755 (5)0.09730*
H150.698 (1)0.089 (1)0.4688 (6)0.07930*
H190.900600.405800.400800.06260*
H21A1.099100.334900.256600.08820*
H21B1.121700.334600.332200.08820*
H22A0.8251 (9)0.3916 (7)0.2285 (4)0.10400*
H22B0.864 (1)0.2557 (9)0.2183 (5)0.10400*
H22C0.729800.290600.258300.10400*
H23A0.968000.198400.384100.09380*
H23B0.819300.170800.355400.09380*
H23C0.9534 (8)0.1359 (7)0.3153 (4)0.09380*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0829 (2)0.0454 (3)0.1540 (2)0.0116 (2)0.0345 (2)0.0171 (2)
O10.0356 (2)0.0673 (3)0.0410 (2)0.0126 (2)0.0085 (2)0.0065 (2)
O20.0390 (2)0.0707 (3)0.0469 (2)0.0025 (2)0.0023 (2)0.0130 (2)
O30.0458 (3)0.0607 (4)0.0416 (3)0.0018 (3)0.0061 (3)0.0040 (3)
O40.0716 (3)0.0793 (3)0.0542 (3)0.0118 (2)0.0202 (2)0.0063 (2)
O50.1035 (3)0.0546 (4)0.1158 (3)0.0090 (3)0.0386 (2)0.0050 (3)
O60.0598 (3)0.0747 (3)0.1016 (5)0.0047 (2)0.0390 (3)0.0160 (3)
N10.0340 (4)0.0408 (4)0.0391 (4)0.0025 (3)0.0016 (3)0.0007 (3)
C10.0380 (3)0.0350 (3)0.0395 (3)0.0044 (2)0.0080 (3)0.0010 (3)
C20.0344 (3)0.0424 (3)0.0421 (4)0.0059 (2)0.0041 (3)0.0001 (3)
C30.0362 (3)0.0441 (3)0.0487 (3)0.0036 (3)0.0094 (3)0.0024 (3)
C40.0328 (3)0.0407 (4)0.0560 (3)0.0045 (3)0.0100 (3)0.0010 (3)
C50.0506 (3)0.0559 (3)0.0637 (3)0.0132 (2)0.0049 (2)0.0071 (2)
C60.0643 (4)0.0527 (4)0.0912 (5)0.0216 (3)0.0168 (3)0.0166 (4)
C70.0511 (3)0.0390 (3)0.1032 (3)0.0039 (2)0.0255 (3)0.0046 (2)
C80.0472 (5)0.0574 (4)0.0870 (5)0.0012 (4)0.0089 (4)0.0218 (3)
C90.0403 (3)0.0537 (4)0.0664 (3)0.0064 (3)0.0003 (3)0.0089 (3)
C100.0415 (4)0.0517 (5)0.0403 (4)0.0001 (3)0.0035 (4)0.0014 (3)
C110.0457 (4)0.0505 (4)0.0474 (4)0.0040 (3)0.0064 (3)0.0056 (3)
C120.0724 (3)0.0733 (3)0.0577 (3)0.0130 (2)0.0097 (2)0.0202 (2)
C130.0847 (5)0.0672 (4)0.0935 (6)0.0091 (3)0.0294 (5)0.0397 (4)
C140.0643 (4)0.0562 (4)0.1113 (7)0.0093 (3)0.0174 (4)0.0188 (4)
C150.0453 (4)0.0468 (5)0.0858 (6)0.0055 (3)0.0058 (4)0.0015 (4)
C160.0334 (5)0.0429 (5)0.0519 (8)0.0019 (4)0.0032 (5)0.0005 (5)
C170.0304 (4)0.0419 (6)0.0410 (5)0.0040 (4)0.0019 (4)0.0035 (4)
C180.0543 (6)0.0568 (8)0.0673 (5)0.0053 (5)0.0187 (4)0.0056 (5)
C190.0318 (3)0.0540 (4)0.0419 (5)0.0062 (3)0.0069 (3)0.0019 (3)
C200.0432 (6)0.0604 (5)0.0437 (7)0.0128 (5)0.0066 (5)0.0039 (5)
C210.0518 (6)0.0790 (5)0.0738 (5)0.0208 (4)0.0225 (5)0.0060 (4)
C220.0793 (5)0.1143 (5)0.0581 (4)0.0322 (4)0.0087 (4)0.0266 (4)
C230.0880 (4)0.0587 (4)0.0746 (4)0.0130 (3)0.0116 (3)0.0058 (3)
Geometric parameters (Å, º) top
F1—C71.359 (1)C5—C61.391 (1)
O1—C11.351 (1)C6—C71.358 (2)
O1—C191.431 (1)C7—C81.359 (1)
O2—C11.196 (1)C8—C91.393 (1)
O4—C101.212 (1)C10—C111.479 (2)
O3—C171.208 (2)C11—C121.383 (1)
O5—C181.192 (2)C11—C161.382 (2)
O6—C181.345 (2)C12—C131.395 (1)
O6—C211.456 (1)C13—C141.365 (2)
N1—C31.456 (1)C14—C151.374 (2)
N1—C101.390 (2)C15—C161.380 (2)
N1—C171.399 (2)C16—C171.481 (2)
C1—C21.512 (1)C18—C191.511 (2)
C2—C31.539 (1)C19—C201.525 (2)
C2—C41.518 (1)C20—C211.531 (2)
C4—C51.385 (1)C20—C221.517 (2)
C4—C91.383 (1)C20—C231.518 (2)
C1—O1—C19116.7 (1)C10—C11—C16107.9 (1)
C18—O6—C21109.8 (1)C12—C11—C16120.8 (1)
C3—N1—C10123.6 (1)C11—C12—C13116.6 (1)
C3—N1—C17124.8 (1)C12—C13—C14122.1 (1)
C10—N1—C17111.6 (1)C13—C14—C15121.4 (1)
O1—C1—O2123.9 (1)C14—C15—C16117.2 (1)
O1—C1—C2110.9 (1)C11—C16—C15121.9 (1)
O2—C1—C2125.2 (1)C11—C16—C17108.5 (1)
C1—C2—C3109.6 (1)C15—C16—C17129.5 (1)
C1—C2—C4111.1 (1)O3—C17—N1125.2 (1)
C3—C2—C4111.3 (1)O3—C17—C16129.3 (1)
N1—C3—C2110.8 (1)N1—C17—C16105.5 (1)
C2—C4—C5120.1 (1)O5—C18—O6122.3 (1)
C2—C4—C9121.6 (1)O5—C18—C19129.9 (1)
C5—C4—C9118.4 (1)O6—C18—C19107.8 (1)
C4—C5—C6120.9 (1)O1—C19—C18110.0 (1)
C5—C6—C7118.5 (1)O1—C19—C20114.4 (1)
F1—C7—C6118.3 (1)C18—C19—C20104.0 (1)
F1—C7—C8118.8 (1)C19—C20—C2197.8 (1)
C6—C7—C8122.9 (1)C19—C20—C22111.5 (1)
C7—C8—C9118.2 (1)C19—C20—C23113.4 (1)
C4—C9—C8121.1 (1)C21—C20—C22110.4 (1)
O4—C10—N1124.2 (1)C21—C20—C23111.5 (1)
O4—C10—C11129.5 (1)C22—C20—C23111.5 (1)
N1—C10—C11106.3 (1)O6—C21—C20105.7 (1)
C10—C11—C12131.3 (1)
C19—O1—C1—O21.6 (1)C6—C7—C8—C90.5 (1)
C19—O1—C1—C2178.5 (1)C7—C8—C9—C40.1 (1)
C1—O1—C19—C18132.2 (1)O4—C10—C11—C123.6 (1)
C1—O1—C19—C20111.2 (1)O4—C10—C11—C16178.8 (2)
C21—O6—C18—O5177.7 (2)N1—C10—C11—C12175.6 (2)
C21—O6—C18—C192.8 (1)N1—C10—C11—C162.0 (1)
C18—O6—C21—C2021.6 (1)C10—C11—C12—C13177.4 (2)
C3—N1—C10—O45.5 (1)C10—C11—C16—C15178.3 (2)
C10—N1—C3—C266.2 (1)C10—C11—C16—C170.7 (1)
C3—N1—C10—C11173.7 (1)C16—C11—C12—C130.1 (1)
C3—N1—C17—O36.6 (1)C12—C11—C16—C150.5 (1)
C17—N1—C3—C2111.4 (1)C12—C11—C16—C17178.6 (2)
C3—N1—C17—C16173.3 (1)C11—C12—C13—C140.1 (1)
C17—N1—C10—O4176.6 (2)C12—C13—C14—C150.0 (1)
C10—N1—C17—O3175.6 (2)C13—C14—C15—C160.3 (1)
C17—N1—C10—C114.1 (1)C14—C15—C16—C110.6 (1)
C10—N1—C17—C164.5 (1)C14—C15—C16—C17178.2 (2)
O1—C1—C2—C3142.1 (1)C11—C16—C17—O3177.0 (2)
O1—C1—C2—C494.5 (1)C11—C16—C17—N13.1 (1)
O2—C1—C2—C338.0 (1)C15—C16—C17—O34.1 (1)
O2—C1—C2—C485.4 (1)C15—C16—C17—N1175.8 (2)
C1—C2—C3—N156.3 (1)O5—C18—C19—O131.5 (1)
C1—C2—C4—C5130.2 (1)O5—C18—C19—C20154.5 (2)
C1—C2—C4—C950.2 (1)O6—C18—C19—O1149.0 (1)
C4—C2—C3—N1179.6 (1)O6—C18—C19—C2026.0 (1)
C3—C2—C4—C5107.4 (1)O1—C19—C20—C21156.1 (1)
C3—C2—C4—C972.2 (1)O1—C19—C20—C2240.5 (1)
C2—C4—C5—C6179.9 (1)O1—C19—C20—C2386.4 (1)
C2—C4—C9—C8179.9 (1)C18—C19—C20—C2136.0 (1)
C9—C4—C5—C60.5 (1)C18—C19—C20—C2279.6 (1)
C5—C4—C9—C80.3 (1)C18—C19—C20—C23153.6 (1)
C4—C5—C6—C70.1 (1)C19—C20—C21—O635.2 (1)
C5—C6—C7—F1179.2 (1)C22—C20—C21—O681.3 (1)
C5—C6—C7—C80.4 (1)C23—C20—C21—O6154.2 (1)
F1—C7—C8—C9179.1 (1)
(II) top
Crystal data top
C25H25NO8·0.5C4H8O2Dx = 1.29 Mg m3
Mr = 511.53Mo Kα radiation, λ = 0.71073 Å
Monoclinic, P21Cell parameters from 11342 reflections
a = 11.560 (1) Åθ = 1–25.4°
b = 8.400 (1) ŵ = 0.10 mm1
c = 13.954 (1) ÅT = 298 K
β = 103.41 (1)°Prism, colorless
V = 1318.1 (4) Å30.4 × 0.3 × 0.3 mm
Z = 2
Data collection top
KappaCCD
diffractometer
Rint = 0.028
phi–scanθmax = 25.4°
10968 measured reflectionsh = 1314
2742 independent reflectionsk = 89
2547 reflections with refl_observed_if_I_ > _1.00_σ(I)l = 1716
Refinement top
Refinement on FH-atom parameters not refined
R[F2 > 2σ(F2)] = 0.062 w = 1/[σ2(F) + 0.05F2]
wR(F2) = 0.098(Δ/σ)max = 0.047
S = 1.65Δρmax = 0.23 e Å3
2547 reflectionsΔρmin = 0.25 e Å3
313 parameters
Crystal data top
C25H25NO8·0.5C4H8O2V = 1318.1 (4) Å3
Mr = 511.53Z = 2
Monoclinic, P21Mo Kα radiation
a = 11.560 (1) ŵ = 0.10 mm1
b = 8.400 (1) ÅT = 298 K
c = 13.954 (1) Å0.4 × 0.3 × 0.3 mm
β = 103.41 (1)°
Data collection top
KappaCCD
diffractometer
2547 reflections with refl_observed_if_I_ > _1.00_σ(I)
10968 measured reflectionsRint = 0.028
2742 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.062313 parameters
wR(F2) = 0.098H-atom parameters not refined
S = 1.65Δρmax = 0.23 e Å3
2547 reflectionsΔρmin = 0.25 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.3230 (2)0.183000.3084 (1)0.047 (1)
O20.2266 (2)0.1958 (3)0.1492 (1)0.062 (1)
O30.0848 (2)0.0758 (3)0.3483 (2)0.070 (1)
O40.0353 (2)0.0082 (3)0.0357 (1)0.068 (1)
O70.1844 (2)0.8305 (3)0.2152 (2)0.047 (1)
O80.1717 (2)0.9066 (3)0.3914 (2)0.055 (1)
O60.6241 (2)0.2507 (3)0.3099 (2)0.101 (1)
O50.4753 (2)0.4319 (3)0.2730 (2)0.131 (1)
O90.4952 (2)0.2054 (4)0.0006 (2)0.250 (1)0.50
O100.5002 (2)0.4256 (4)0.0592 (2)0.250 (1)0.50
N10.0415 (2)0.0765 (4)0.1955 (2)0.040 (1)
C10.2271 (2)0.2088 (4)0.2346 (2)0.043 (2)
C20.1222 (2)0.2588 (4)0.2759 (2)0.041 (1)
C30.0040 (2)0.2402 (4)0.1998 (2)0.050 (2)
C40.1374 (2)0.4321 (4)0.3096 (2)0.039 (1)
C50.1575 (2)0.5498 (4)0.2454 (2)0.038 (1)
C60.1674 (2)0.7069 (4)0.2739 (2)0.034 (2)
C70.1583 (2)0.7477 (4)0.3688 (2)0.039 (1)
C80.1378 (3)0.6314 (4)0.4326 (2)0.042 (2)
C90.1273 (2)0.4744 (3)0.4010 (2)0.044 (1)
C100.0582 (2)0.0234 (4)0.1142 (2)0.044 (2)
C110.1126 (3)0.1722 (4)0.1433 (2)0.041 (2)
C160.1284 (3)0.1507 (4)0.2367 (2)0.041 (2)
C170.0834 (3)0.0094 (4)0.2711 (2)0.044 (2)
C190.4318 (3)0.1480 (4)0.2814 (3)0.052 (2)
C200.5133 (3)0.0328 (5)0.3501 (3)0.054 (2)
C240.2096 (3)0.7907 (4)0.1216 (2)0.060 (2)
C120.1472 (3)0.3096 (5)0.0918 (3)0.055 (2)
C130.2009 (3)0.4239 (4)0.1364 (2)0.061 (2)
C140.2171 (3)0.4053 (5)0.2306 (2)0.072 (2)
C150.1797 (3)0.2670 (5)0.2835 (3)0.060 (2)
C180.5075 (3)0.2968 (4)0.2876 (3)0.088 (2)
C210.6298 (3)0.0805 (5)0.3256 (3)0.076 (2)
C220.5158 (4)0.0706 (6)0.4571 (3)0.085 (3)
C230.485 (1)0.141 (1)0.3256 (7)0.08 (4)
C250.1737 (9)0.951 (2)0.492 (1)0.07 (5)
C260.466 (1)0.367 (1)0.002 (1)0.25 (5)0.50
C280.5549 (8)0.089 (2)0.008 (1)0.25 (3)0.50
C270.423 (1)0.471 (3)0.070 (2)0.25 (8)0.50
C290.662 (2)0.152 (1)0.078 (2)0.25 (5)0.50
H20.122 (5)0.193 (9)0.325 (5)0.05970*
H3A0.060 (6)0.298 (9)0.220 (5)0.06730*
H3B0.007 (5)0.278 (8)0.126 (5)0.06730*
H50.154 (5)0.506 (8)0.187 (5)0.05710*
H80.121 (5)0.655 (9)0.496 (5)0.06140*
H90.112 (4)0.392 (7)0.437 (4)0.06360*
H120.126 (7)0.34 (1)0.031 (6)0.07360*
H130.205 (8)0.51 (1)0.100 (7)0.07840*
H140.254 (5)0.524 (8)0.262 (4)0.09020*
H150.195 (5)0.240 (8)0.334 (5)0.07930*
H190.413 (7)0.11 (1)0.216 (5)0.07140*
H21A0.708 (6)0.06 (1)0.368 (5)0.09440*
H21B0.63 (1)0.01 (2)0.266 (8)0.09440*
H22A0.530 (8)0.21 (1)0.480 (7)0.10300*
H22B0.578 (8)0.03 (1)0.499 (6)0.10300*
H22C0.437 (6)0.054 (9)0.466 (5)0.10300*
H23A0.482 (7)0.15 (1)0.243 (6)0.09520*
H23B0.393 (5)0.195 (8)0.346 (5)0.09520*
H23C0.554 (7)0.21 (1)0.388 (6)0.09520*
H24A0.207 (9)0.90 (1)0.092 (7)0.07960*
H24B0.114 (9)0.74 (1)0.073 (8)0.07960*
H24C0.276 (8)0.74 (1)0.135 (6)0.07960*
H25A0.171 (8)1.07 (1)0.496 (6)0.09050*
H25B0.252 (8)0.92 (1)0.554 (6)0.09050*
H25C0.095 (7)0.92 (1)0.506 (5)0.09050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.035 (1)0.056 (1)0.049 (1)0.0049 (9)0.0094 (9)0.0010 (9)
O20.066 (2)0.074 (1)0.041 (1)0.0126 (9)0.005 (1)0.0007 (9)
O30.053 (2)0.089 (1)0.068 (1)0.013 (1)0.026 (1)0.038 (1)
O40.083 (1)0.072 (1)0.045 (1)0.0162 (9)0.016 (1)0.0120 (9)
O70.067 (1)0.034 (1)0.039 (1)0.002 (1)0.020 (1)0.001 (1)
O80.077 (1)0.039 (2)0.046 (2)0.002 (1)0.018 (1)0.007 (1)
O60.054 (1)0.101 (1)0.144 (1)0.023 (1)0.030 (1)0.002 (1)
O50.128 (2)0.060 (2)0.205 (2)0.008 (1)0.072 (1)0.025 (1)
O90.246 (2)0.246 (1)0.246 (1)0.000 (1)0.057 (1)0.000 (1)
O100.246 (2)0.246 (2)0.246 (2)0.000 (1)0.057 (1)0.000 (1)
N10.034 (2)0.041 (2)0.043 (2)0.007 (1)0.007 (1)0.005 (1)
C10.041 (2)0.032 (2)0.051 (2)0.002 (1)0.001 (1)0.002 (1)
C20.040 (1)0.032 (2)0.047 (2)0.002 (1)0.004 (1)0.005 (1)
C30.039 (2)0.038 (2)0.065 (2)0.000 (1)0.001 (1)0.001 (1)
C40.032 (2)0.036 (2)0.046 (2)0.001 (1)0.005 (1)0.004 (1)
C50.041 (2)0.038 (1)0.032 (2)0.003 (1)0.004 (1)0.000 (1)
C60.037 (2)0.031 (2)0.032 (2)0.002 (1)0.008 (2)0.004 (1)
C70.035 (2)0.034 (2)0.046 (2)0.002 (1)0.006 (1)0.004 (1)
C80.045 (2)0.045 (2)0.034 (2)0.001 (1)0.012 (1)0.006 (1)
C90.047 (2)0.043 (1)0.041 (2)0.001 (1)0.011 (1)0.009 (1)
C100.041 (2)0.047 (2)0.040 (3)0.002 (1)0.008 (2)0.004 (2)
C110.040 (3)0.044 (2)0.034 (2)0.001 (1)0.004 (2)0.002 (1)
C160.030 (2)0.050 (2)0.042 (2)0.004 (1)0.009 (1)0.002 (1)
C170.032 (2)0.056 (2)0.043 (2)0.001 (1)0.009 (1)0.006 (2)
C190.043 (3)0.058 (2)0.053 (4)0.001 (2)0.017 (3)0.001 (2)
C200.036 (2)0.065 (2)0.056 (3)0.001 (2)0.004 (2)0.000 (2)
C240.086 (2)0.044 (2)0.049 (2)0.004 (1)0.025 (2)0.006 (1)
C120.059 (2)0.048 (3)0.055 (3)0.004 (2)0.013 (2)0.009 (2)
C130.069 (3)0.045 (2)0.062 (2)0.003 (2)0.004 (2)0.006 (2)
C140.062 (2)0.055 (2)0.095 (2)0.014 (2)0.017 (2)0.018 (2)
C150.054 (2)0.065 (2)0.059 (3)0.012 (2)0.021 (2)0.002 (2)
C180.072 (2)0.080 (2)0.112 (2)0.017 (2)0.040 (2)0.000 (2)
C210.044 (2)0.089 (3)0.090 (2)0.002 (2)0.016 (2)0.000 (2)
C220.071 (3)0.123 (3)0.056 (4)0.027 (2)0.013 (3)0.004 (2)
C230.06 (6)0.06 (4)0.11 (3)0.01 (3)0.00 (3)0.01 (3)
C250.12 (7)0.05 (6)0.04 (4)0.01 (5)0.02 (5)0.01 (4)
C260.25 (4)0.25 (7)0.25 (7)0.00 (4)0.06 (5)0.00 (5)
C280.25 (4)0.25 (6)0.25 (4)0.00 (3)0.06 (3)0.00 (3)
C270.25 (8)0.2 (1)0.25 (5)0.00 (7)0.06 (5)0.00 (6)
C290.25 (6)0.25 (6)0.25 (5)0.00 (4)0.06 (4)0.00 (4)
Geometric parameters (Å, º) top
O1—C11.344 (4)C4—C91.355 (4)
O1—C191.425 (4)C5—C61.375 (5)
O2—C11.195 (4)C6—C71.395 (4)
O3—C171.217 (4)C7—C81.379 (5)
O4—C101.214 (4)C8—C91.387 (5)
O7—C61.365 (4)C10—C111.497 (5)
O7—C241.442 (4)C11—C161.369 (5)
O8—C71.372 (5)C11—C121.369 (6)
O8—C251.45 (2)C16—C171.481 (5)
O6—C181.367 (4)C16—C151.383 (5)
O6—C211.446 (6)C19—C201.525 (6)
O5—C181.197 (5)C19—C181.517 (5)
O9—C261.40 (2)C20—C211.518 (6)
O9—C281.19 (2)C20—C221.520 (6)
N1—C31.468 (5)C20—C231.52 (2)
N1—C101.388 (5)C12—C131.369 (6)
N1—C171.379 (5)C13—C141.379 (5)
C1—C21.518 (4)C14—C151.390 (6)
C2—C31.532 (4)C26—C271.50 (3)
C2—C41.527 (5)C28—C27i1.54 (3)
C4—C51.389 (5)C28—C291.48 (3)
C1—O1—C19116.9 (3)C10—C11—C12130.6 (4)
C6—O7—C24117.1 (3)C16—C11—C12121.6 (4)
C7—O8—C25116.5 (6)C11—C16—C17108.3 (3)
C18—O6—C21108.8 (3)C11—C16—C15121.5 (4)
C26—O9—C28159.0 (10)C17—C16—C15130.2 (3)
C3—N1—C10125.5 (3)O3—C17—N1124.7 (4)
C3—N1—C17122.5 (3)O3—C17—C16128.9 (3)
C10—N1—C17111.8 (3)N1—C17—C16106.4 (3)
O1—C1—O2124.2 (3)O1—C19—C20114.8 (3)
O1—C1—C2110.1 (3)O1—C19—C18110.4 (3)
O2—C1—C2125.8 (3)C20—C19—C18102.9 (3)
C1—C2—C3111.8 (3)C19—C20—C2198.2 (3)
C1—C2—C4109.6 (3)C19—C20—C22110.7 (4)
C3—C2—C4109.3 (3)C19—C20—C23113.6 (5)
N1—C3—C2112.2 (3)C21—C20—C22110.5 (4)
C2—C4—C5120.3 (3)C21—C20—C23111.0 (6)
C2—C4—C9120.7 (3)C22—C20—C23112.1 (5)
C5—C4—C9119.0 (3)C11—C12—C13117.4 (4)
C4—C5—C6120.8 (3)C12—C13—C14122.0 (4)
O7—C6—C5124.8 (3)C13—C14—C15120.4 (4)
O7—C6—C7115.8 (3)C16—C15—C14117.0 (4)
C5—C6—C7119.4 (3)O6—C18—O5124.0 (4)
O8—C7—C6115.3 (3)O6—C18—C19107.8 (3)
O8—C7—C8124.6 (3)O5—C18—C19128.2 (4)
C6—C7—C8120.1 (3)O6—C21—C20106.5 (3)
C7—C8—C9118.9 (3)O9—C26—C27132.5 (16)
C4—C9—C8121.9 (3)O9—C28—C27i130.2 (13)
O4—C10—N1125.9 (4)O9—C28—C2998.6 (11)
O4—C10—C11128.3 (4)C27i—C28—C29116.3 (12)
N1—C10—C11105.7 (3)C26—C27—C28i76.2 (13)
C10—C11—C16107.8 (3)
C19—O1—C1—O24.2 (3)O7—C6—C7—C8178.2 (5)
C19—O1—C1—C2174.9 (4)C5—C6—C7—O8178.7 (5)
C1—O1—C19—C20146.4 (4)C5—C6—C7—C81.0 (3)
C1—O1—C19—C1898.0 (4)O8—C7—C8—C9179.2 (5)
C24—O7—C6—C58.7 (3)C6—C7—C8—C90.4 (3)
C24—O7—C6—C7172.1 (4)C7—C8—C9—C40.4 (3)
C25—O8—C7—C6174.5 (7)O4—C10—C11—C16176.4 (5)
C25—O8—C7—C85.2 (7)O4—C10—C11—C121.8 (4)
C21—O6—C18—O5178.2 (5)N1—C10—C11—C161.9 (3)
C21—O6—C18—C194.0 (3)N1—C10—C11—C12179.9 (5)
C18—O6—C21—C2021.5 (3)C10—C11—C16—C171.0 (3)
C28—O9—C26—C27103 (3)C10—C11—C16—C15178.6 (5)
C26—O9—C28—C2926 (2)C10—C11—C12—C13176.5 (6)
C3—N1—C10—O41.8 (3)C12—C11—C16—C17179.3 (5)
C10—N1—C3—C2117.0 (4)C16—C11—C12—C131.5 (4)
C3—N1—C10—C11176.6 (4)C12—C11—C16—C150.2 (4)
C3—N1—C17—O31.6 (3)C11—C16—C17—O3177.3 (5)
C17—N1—C3—C269.3 (4)C11—C16—C17—N10.4 (3)
C3—N1—C17—C16176.2 (4)C11—C16—C15—C141.5 (4)
C10—N1—C17—O3176.1 (5)C15—C16—C17—O32.2 (4)
C17—N1—C10—O4176.1 (5)C15—C16—C17—N1179.9 (5)
C17—N1—C10—C112.3 (3)C17—C16—C15—C14178.0 (6)
C10—N1—C17—C161.7 (3)O1—C19—C20—C21157.3 (4)
O1—C1—C2—C3162.5 (4)O1—C19—C20—C2241.7 (4)
O1—C1—C2—C476.1 (3)O1—C19—C20—C2385.5 (6)
O2—C1—C2—C318.4 (3)O1—C19—C18—O6150.4 (4)
O2—C1—C2—C4103.0 (4)O1—C19—C18—O532.0 (4)
C1—C2—C3—N183.0 (3)C20—C19—C18—O627.5 (3)
C1—C2—C4—C553.4 (3)C20—C19—C18—O5154.9 (5)
C1—C2—C4—C9129.0 (4)C18—C19—C20—C2137.4 (3)
C4—C2—C3—N1155.4 (4)C18—C19—C20—C2278.2 (4)
C3—C2—C4—C569.5 (3)C18—C19—C20—C23154.6 (6)
C3—C2—C4—C9108.1 (4)C19—C20—C21—O636.5 (3)
C2—C4—C5—C6177.8 (5)C22—C20—C21—O679.3 (4)
C2—C4—C9—C8178.4 (5)C23—C20—C21—O6155.7 (6)
C9—C4—C5—C60.2 (3)C11—C12—C13—C141.9 (4)
C5—C4—C9—C80.8 (3)C12—C13—C14—C150.6 (4)
C4—C5—C6—O7178.4 (5)C13—C14—C15—C161.1 (4)
C4—C5—C6—C70.7 (3)C27—C28—O9—C26110 (3)
O7—C6—C7—O82.1 (3)C28—C27—C26—O9174 (2)
Symmetry code: (i) x+1, y+1/2, z.

Experimental details

(I)(II)
Crystal data
Chemical formulaC23H20FNO6C25H25NO8·0.5C4H8O2
Mr425.41511.53
Crystal system, space groupOrthorhombic, P212121Monoclinic, P21
Temperature (K)298298
a, b, c (Å)9.5666 (3), 11.1026 (2), 20.3200 (6)11.560 (1), 8.400 (1), 13.954 (1)
α, β, γ (°)90.00 (1), 90.00 (1), 90.00 (1)90.00 (1), 103.41 (1), 90.00 (1)
V3)2158.3 (2)1318.1 (4)
Z42
Radiation typeMo KαMo Kα
µ (mm1)0.10.10
Crystal size (mm)0.32 × 0.27 × 0.100.4 × 0.3 × 0.3
Data collection
DiffractometerKappaCCD
diffractometer
KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed reflections
13240, 2362, 2209 [refl_observed_if_I_ > _3.00_σ(I)]10968, 2742, 2547 [refl_observed_if_I_ > _1.00_σ(I)]
Rint0.0280.028
(sin θ/λ)max1)0.6040.604
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.052, 1.22 0.062, 0.098, 1.65
No. of reflections22092547
No. of parameters273313
No. of restraints??
H-atom treatmentH-atom parameters not refinedH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.10, 0.100.23, 0.25

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), maXus (Mackay et al., 1999), ORTEPII (Johnson, 1976), maXus.

Selected geometric parameters (Å, º) for (I) top
O1—C11.351 (1)C1—C21.512 (1)
O1—C191.431 (1)C2—C31.539 (1)
O2—C11.196 (1)C2—C41.518 (1)
N1—C31.456 (1)
C1—O1—C19116.7 (1)C1—C2—C3109.6 (1)
O1—C1—O2123.9 (1)C1—C2—C4111.1 (1)
O1—C1—C2110.9 (1)C3—C2—C4111.3 (1)
O2—C1—C2125.2 (1)N1—C3—C2110.8 (1)
C19—O1—C1—C2178.5 (1)O1—C1—C2—C3142.1 (1)
Selected geometric parameters (Å, º) for (II) top
O1—C11.344 (4)C1—C21.518 (4)
O1—C191.425 (4)C2—C31.532 (4)
O2—C11.195 (4)C2—C41.527 (5)
N1—C31.468 (5)
C1—O1—C19116.9 (3)C1—C2—C3111.8 (3)
O1—C1—O2124.2 (3)C1—C2—C4109.6 (3)
O1—C1—C2110.1 (3)C3—C2—C4109.3 (3)
O2—C1—C2125.8 (3)N1—C3—C2112.2 (3)
C19—O1—C1—C2174.9 (4)O1—C1—C2—C3162.5 (4)
 

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