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Spiro scaffolds are being increasingly utilized in drug discovery due to their inherent three-dimensionality and structural variations, resulting in new syn­thetic routes to introduce spiro building blocks into more pharmaceutically active mol­ecules. Multicomponent cascade reactions, involving the in situ generation of carbonyl ylides from α-diazo­carbonyl compounds and aldehydes, and 1,3-dipolar cyclo­additon with 3-aryl­ideneoxindoles gave a novel class of di­spiro­oxindole derivatives, namely 1,1′′-dibenzyl-5′-(4-chloro­phen­yl)-4′-phenyl-4′,5′-di­hydro­dispiro­[indoline-3,2′-furan-3′,3′′-indoline]-2,2′′-dione, C44H33ClN2O3, (I), 1′′-acetyl-1-benzyl-5′-(4-chloro­phen­yl)-4′-phenyl-4′,5′-di­hydro­dispiro­[in­dol­ine-3,2′-furan-3′,3′′-indoline]-2,2′′-dione, C39H29ClN2O4, (II), 1′′-acetyl-1-benzyl-4′,5′-diphenyl-4′,5′-di­hydro­dispiro­[indoline-3,2′-furan-3′,3′′-indoline]-2,2′′-dione, C39H30N2O4, (III), and 1′′-acetyl-1-benzyl-4′,5′-diphenyl-4′,5′-di­hydro­dispiro­[indoline-3,2′-furan-3′,3′′-indoline]-2,2′′-dione aceto­nitrile hemisolvate, C39H30N2O4·0.5C2H3N, (IV). All four compounds exist as racemic mixtures of the SSSR and RRRS stereoisomers. In these structures, the two H atoms of the di­hydro­furan ring and the two substituted oxindole rings are in a trans orientation, facilitating intra­molecular C—H...O and π–π inter­actions. These weak inter­actions play a prominent role in the structural stability and aid the highly regio- and diastereoselective synthesis. In each of the four structures, the mol­ecular assembly in the crystal is also governed by weak noncovalent inter­actions. Compound (IV) is the solvated analogue of (III) and the two compounds show similar structural features.

Supporting information

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Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615019610/eg3191sup1.cif
Contains datablocks I, II, III, IV, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615019610/eg3191Isup2.hkl
Contains datablock I

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Structure factor file (CIF format) https://doi.org/10.1107/S2053229615019610/eg3191IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615019610/eg3191IIIsup4.hkl
Contains datablock III

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Structure factor file (CIF format) https://doi.org/10.1107/S2053229615019610/eg3191IVsup5.hkl
Contains datablock IV

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Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615019610/eg3191Isup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615019610/eg3191IIsup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615019610/eg3191IIIsup8.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615019610/eg3191IVsup9.cml
Supplementary material

CCDC references: 1431626; 1431625; 1431624; 1431623

Introduction top

\ Oxindole is the core structure in a variety of natural products and drugs. Oxindole derivatives (Klein & Taylor, 2011) have demonstrated significant potential for use in a wide range of biological applications such as NMDA antagonist (Kang et al., 2002), calcium channel blockers (Swensen et al., 2012) anti­angiogenic (Whatmore et al., 2002), anti­cancer (Peddibhotla, 2009) and analgesic effects (Abbadie et al., 2010). The heterocyclic spiro­oxindole ring system is a recurring structural element that has been identified in numerous naturally occurring substances (Williams & Cox, 2003), characterized by highly pronounced biological properties, and pharmacologically active compounds. These spiro-fused ring systems display stereochemical and structural complexities that continue to challenge the synthetic chemist and as a consequence, a number of methods have been reported for the preparation of spiro­oxindole-fused heterocycles (Jadidi et al., 2009; Badillo et al., 2011; Esmaeili et al., 2011; Kiruthika et al., 2011). Isatin is probably one of the most commonly used reagents for constructing spiro­oxindoles in many reactions such as 1,3-dipolar cyclo­addition, Morita–Baylis–Hillman reaction and other condensation reactions (Hong & Wang, 2013; Shi et al., 2012). Over the past few years, multicomponent reactions based on the versatile reactivity of isatins have emerged as efficient methods for the synthesis of various spiro­oxindoles (Basavaiah & Reddy, 2007; Cao et al., 2014). Reddy et al. (2015) reported a domino three-component synthesis of di­spiro­oxindoles through [3+2] cyclo­addition of carbonyl ylides with 3-aryl­ideneoxindoles. In continuation of our previous studies on di­spiro­oxindoles (Ravikumar et al., 2015a,b), we report herein the structural studies of new benzyl and acetyl derivatives, namely 1,1''-di­benzyl-5'-(4-chloro­phenyl)-4'-phenyl-4',5'-di­hydro­dispiro­[indoline-3,\ 2'-furan-3',3''-indoline]-2,2''-dione, (I), 1''-acetyl-1-benzyl-5'-(4-chloro­phenyl)-4'-phenyl-4',5'-\ di­hydro­dispiro­[indoline-3,2'-furan-3',3''-indoline]-2,2''-dione, (II), 1''-acetyl-1-benzyl-4',5'-di­phenyl-4',5'-di­hydro­dispiro­[indoline-3,2'-furan-\ 3',3''-indoline]-2,2''-dione, (III), and 1''-acetyl-1-benzyl-4',5'-di­phenyl-4',5'-di­hydro­dispiro­[indoline-3,2'-furan-\ 3',3''-indoline]-2,2''-dione aceto­nitrile hemisolvate, (IV). The primary goal for the X-ray analyses of the title compounds was to confirm the stereochemistries of the molecules and to obtain detailed information on the structural conformation that may be useful in understanding the chemical reactivity.

Experimental top

Synthesis and crystallization top

The syntheses of compounds (I), (II) and (III) has been described by Reddy et al. (2015). Colourless well-shaped crystals were grown by dissolving 20 mg of (I), (II) and (III) in a methanol–di­chloro­methane mixture (20 ml, 1:1 v/v), followed by slow evaporation of the solvent mixture under ambient conditions over a period of 3–4 d. Crystals of (IV) were obtained by slow evaporation of a solution of compound (III) in aceto­nitrile (10 ml).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. Crystal data, data collection and structure refinement details are summarized in Table 1. All C-bound H atoms of (I), (II), (III) and (IV) were located in difference density maps but were positioned geometrically and included as riding atoms, with C—H = 0.93–0.98 Å and with Uiso(H) values of 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) otherwise. The site-occupancy factors of disordered atoms N3/C40/C41 of the aceto­nitrile solvent molecule of (IV) refined to 0.654 (19) and 0.346 (19). The C—C and C—N distances of the disordered groups were restrainted to 1.55 (2)and 1.15 (2) Å, respectively. A similarity restraint (the command SIMU within SHELXL2014; Sheldrick, 2015) was applied to N3—C40—C41. Owing to poor quality and diffraction ability of the crystal, the data set of (III) contains a large number of weak high-angle reflections, which accounts for the high K values in the analysis of variance. Hence, the SHEL command was used to cut off the weak high-angle reflections.

Results and discussion top

The title compounds (I)–(IV) were produced through a three-component coupling reaction between α-diazo­amide, aldehyde and 3-aryl­ideneoxindole using a catalytic amount of Rh2(OAc)4 in a one-pot synthesis. The reaction proceeds via an in situ carbonyl ylide formation followed by 1,3-dipolar cyclo­addition, creating a central heterocyclic furan ring with the simultaneous formation of four contiguous chiral centres (C7, C9, C10 and C11), of which two (C7 and C11) are spiro all-carbon quaternary centres. The presence of four chiral centres leads to the existence of as many as 16 stereoisomers, of which four pairs are enanti­omers (nonsuperimposable mirror-image relationship), whilst the remaining four pairs are diastereomers (nonsuperimposable nonmirror-image relationship). Compounds (I)–(IV) crystallize in centrosymmetric space groups as racemic mixtures (SSSR and RRRS).

As shown in Table 1, compounds (I)–(IV) crystallize in the same triclinic system and the space group P1 with diverse cell dimensions. Compound (IV) is an aceto­nitrile solvate of (III). Apart from (I), compounds (II)–(IV) crystallize with two molecules in the asymmetric unit (Figs. 1–4). A common numbering system has been used for all the structures. The values of the geometrical parameters when applicable to two molecules in (II)–(IV) are denoted as molecule A/molecule B. The four substituents of the central di­hydro­furan ring are arranged in an all-trans configuration, thus avoiding steric hindrance between the aryl groups. The bond lengths (Allen et al., 1987) and angles in all four structures are in agreement with similar structures reported in the literature (Ravikumar et al., 2015b; Girgis et al., 2015). The di­hydro­furan ring adopts an envelope conformation, with atom O2 as the flap in (I), (II), (III) (molecule A) and (IV) (molecule B), while it is twisted on the C9—O2 bond in (III) (molecule B) and (IV) (molecule A). The puckering parameter Φ is 357.4 (4) in (I), 358.1 (4)/191.7 (4) in (II), 185.3 (5)/334.1 (4) in (III) and 332.5 (3)/2.1 (3) in (IV). The expected Φ (Cremer & Pople, 1975) is k × 36° for envelope and k × 36 + 18° for a twisted conformation, where k is an integer.

As reported by Reddy et al. (2015), the [3+2] cyclo­addition reaction can result in two possible di­spiro­cyclic regioisomers, with spiro­centres either at the 1,2-positions (C7 and C11) or at the 1,3-positions (C7 and C10) of the di­hydro­furan ring. Title structures (I)–(IV) confirm the exclusive formation of the 1,2-isomer. The two asymmetric H atoms of di­hydro­furan (H9 and H10) are in a trans orientation in all four structures [H9—C9—C10—H10 = -152° for (I), 145/-154° for (II), 149/-169° for (III) and 171/-150° for (IV)]. Also, the two oxindole rings at the 1,2-positions are in a trans orientation and facilitate the two carbonyl O atoms to participate in intra­molecular C9—H9···O1 and C10—H10···O3 inter­actions with the trans-related H9 and H10 atoms of the di­hydro­furan ring. The t trans orientation also provide C5—H5···O3 and C13—H13···O1 inter­actions between the oxindole rings. Furthermore, the two oxindole rings show a closer proximity to one another, resulting in possible ππ contacts. The distances between the centroids of the pyrrolone rings (N1/C1/C6/C7/C8 and N2/C11/C12/C17/C18) of oxindole are 3.1720 (11) Å in (I), 3.0261 (15)/3.0424 (15) Å in (II), 3.0444 (18)/3.0861 (19) Å in (III) and 3.0430 (13)/3.0451 (12) Å in (IV). The combination of C—H···O and ππ inter­actions facilitates the positioning of the oxindole rings in all the four structures, as also seen in previous structures (Ravikumar et al., 2015b).

The C9 and C10 phenyl rings on the di­hydro­furan ring are twisted to be nearly orthogonal to each other. The dihedral angles between the planes of the phenyl rings are 69.28 (13)° in (I), 80.52 (14)/80.85 (13)° in (II), 75.41 (17)/84.71 (16)° in (III) and 82.68 (11)/75.98 (12)° in (IV). In (II)–(IV), the planar orientation of the acetyl group of the oxindole is governed by an intra­molecular C16—H16···O4 inter­action. The benzyl group at atom N1 of the oxindole ring, substituted at C7 of the di­hydro­furan ring, plays an inter­esting role in all the four structures. The benzyl ring is oriented in such a way that it participates in an intra­molecular C33—H ···π inter­action with the adjacent oxindole phenyl ring (C12–C17), substituted at atom C11 of the di­hydro­furan ring. The presence of a benzyl group in (I) instead of the acetyl group in (II)–(IV) forms a C38—H38A···O3 inter­action. An overlay of (I)–(IV), superimposing the C atoms of the di­hydro­furan ring (Fig. 5), reveals significant dissimilarities in their conformations.

The 1,3-dipolar cyclo­addition reaction involves bond formation between 4π electrons 1,3-dipole (carbonyl ylide) and 2π electrons dipolarophile [(E)-aryl­ideneoxindole] systems. Depending on the nature of rea­cta­nts, the reaction is favored by HOMO–LUMO energy gap (HOMO is the highest occupied molecular orbital and LUMO is the lowest unoccupied molecular orbital) between frontier molecular orbitals (FMO), i.e. HOMO(dipole)–LUMO(dipolarophile) or LUMO(dipole)–HOMO(dipolarophile), or a combination of both. A smaller HOMO–LUMO energy gap normally indicates higher reactivity. Computational calculations were performed for the above said two rea­ctant systems separately, in the absence of the Rh catalyst, using the density functional theory (DFT) methods performed at the B3LYP hybrid exchange correlation functional level (Becke, 1993; Lee et al., 1988) using the 6-31G(d,p) basis set (Bauschlicher & Partridge, 1995) as implemented in GAUSSIAN03 (Frisch et al. , 2004). These calculations are only a rough approximation, suggesting the cyclo­adduct formation between the HOMO of carbonyl ylide and the LUMO of (E)-aryl­ideneoxindole since the HOMO–LUMO energy gap (ΔE = 2.75 eV) is found to be smaller than that of the LUMO of carbonyl ylide and the HOMO of (E)-aryl­ideneoxindole (ΔE = 3.02 eV).

An attempt has been made to rationalize the diastereoselectivity observed in compounds (I)–(IV). The in-situ-generated carbonyl ylide can exist in an equilibrium between the E and Z forms. The presence of the C9—H9···O1 inter­action seen in (I)–(IV) suggests that the [3+2] cyclo­addition reaction might have taken place between the E form of the carbonyl ylide and aryl­ideneoxindole. Computational studies also indicated that the E form of the carbonyl ylide is more stable than the Z form by 4.27 kcal mol-1, stabilized by an intra­molecular C—H···O inter­action. Further, the E form of the carbonyl ylide can add to the aryl­ideneoxindole in two possible ways, either in an exo or an endo fashion, as schematically depicted in Fig. 6. This would lead to an enanti­omerically related exo and endo cyclo­adducts (RRRS and SSSR) as observed in (I)–(IV). The closeness of the oxindole rings could provide secondary stabilizing inter­actions, e.g. ππ and C—H···O, in both the endo and exo forms. In describing the diastereoselective synthesis of 1,2-di­amines, Wang et al. (2003) suggested the importance of intra­molecular inter­actions and the presence of ππ inter­actions. The present structures show a trans orientation of the oxindole rings and the H atoms of the di­hydro­furan ring, facilitating C—H···O and ππ inter­actions which support the role of weak inter­actions in promoting both the regio- and diastereoselectivity of di­spiro­oxindoles.

The molecular assembly in (I)–(IV) is governed by the weak inter­actions (Tables 2–5), as noticed in the prototype oxindole polymorphic systems (Flakus & Hachula, 2011). In (I), two inversion-related di­spiroxindole molecules are linked by symmetry-related C31—H31A···O2i (see Table 2 for the symmetry code) inter­actions between di­hydro­furan O and benzyl CH atoms to form a cyclic centrosymmetric dimer characterized by an R22(12) motif (Etter, 1990; Etter et al., 1990; Bernstein et al., 1995). The dimers are inter­connected by two independent C3—H3···Cg1ii and C27—H27···Cg2iii inter­actions (Cg1 is the centroid of the C32–C37 ring and Cg2 is the centroid of the C1–C6 ring) to form a one-dimensional ribbon along the a axis (Fig. 7). The oxindole rings linked by ππ inter­actions [3.8870 (14)/4.0703 (16) Å for the centroid–centroid distance between the N1/C1/C6/C7/C8 and C1–C6 rings] form centrosymmetric dimers (A···A and B···B) in (II). Adjacent dimers are linked by C15A—H15A···Cg3 inter­actions involving oxindole and phenyl rings (Cg3 is centroid of the C19B–C24B ring) to form a one-dimensional chain diagonally along the ab plane. Further, a C27B—H27B···O1Ai (see Table 3 for symmetry code) inter­action between chloro­phenyl and oxindole rings links these chains and extends the molecules into a two-dimensional network (Fig. 8). In (III), the combination of ππ inter­actions between oxindole rings [3.9256 (19) Å between the centroids of the C12A–C17A and C12B–C117B rings], C31B—H31C···Cg3iv (Cg3 is a centroid of the C25A—C30A ring; see Table 4 for symmetry code) and C24A—H24A···Cg2iii (Cg2 is the centroid of the C32B–C37B ring) inter­actions between benzyl and phenyl rings, form a cyclic tetra­mer. A centrosymmetric C27A—H27A···O1Ai inter­action between phenyl and oxindole rings inter­connect cyclic tetra­mers extending into a one-dimensional ribbon along the b axis. A C3A—H3A···Cg1ii (Cg1 is the centroid of the C19B–C24B ring) inter­action between oxindole and phenyl rings completes a two-dimensional network (Fig. 9).

In (IV), molecules A and B, form independent C—H···O hydrogen-bonded dimers (A···A and B···B) between acetyl and benzyl (C34A—H34A···O4Aii; see Table 5 for the symmetry code), and phenyl and oxindole rings (C27B—H27B···O1Bi). The dimers of molecule A are extended into a one-dimensional ribbon along the a axis by a C39A—H39C···Cg2iv (Cg2 is the centroid of the C32A–C37A ring) inter­action between acetyl and benzyl rings. Molecule B acts as bridging linker between two parallel one-dimensioni ribbons of molecule A, through a C3—H3B···Cg1iii (Cg1 is the centroid of the C19A–C24A ring) inter­action between oxindole and phenyl rings and a C24B—H24B···.Cg2iv inter­action between phenyl and benzyl rings, extending the ribbons into a two-dimensional network (Fig. 10). The aceto­nitrile solvent molecule appears to play only a space-filling role; it is not involved in any inter­action and is instead disordered.

In conclusion, the crystal structures of di­spiroxindole derivatives have revealed salient features for understanding the diastereoselectivity of the [3+2] cyclo­addition reaction occurring during the synthesis of these compounds. Weak inter­actions, viz. C—H···O, ππ and C—H···π, play a significant role in structural stability and molecular assembly.

Computing details top

For all compounds, data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I), (IV); SHELXS97 (Sheldrick, 2015) for (II), (III). For all compounds, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top
[Figure 1] Fig. 1. The molecular conformation of (I) in the crystal, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The dashed lines indicate C—H···O interactions with atoms C9 and C10 as donors.
[Figure 2] Fig. 2. The molecular conformation of (II) in the crystal, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The dashed lines indicate C—H···O interactions with atoms C9 and C10 as donors.
[Figure 3] Fig. 3. The molecular conformation of (III) in the crystal, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The dashed lines indicate C—H···O interactions with atoms C9 and C10 as donors.
[Figure 4] Fig. 4. The molecular conformation of (IV) in the crystal, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The dashed lines indicate C—H···O interactions with atoms C9 and C10 as donors. The minor-diordered components N31/C401/C411 of the acetonitrile solvent have been omitted for clarity.
[Figure 5] Fig. 5. A superposition of the molecular conformations of (I) (red), (IIA) (yellow), (IIB) (blue), (IIIA) (green), (IIIB) (orange), (IVA) (cyan) and (IVB) (magenta). The overlay was made by a least-squares fit through atoms C7/C9/C10/C11 of the dihydrofuran ring. H atoms and the acetonitrile solvent molecule of (IV) have been omitted for clarity.
[Figure 6] Fig. 6. Schematic representation of exo and endo modes of the [3+2] cycloaddition between carbonyl ylide and arylideneoxindole.
[Figure 7] Fig. 7. A partial packing diagram for (I), showing the centrosymmeric C—H···O dimer formation and their propagation into a one-dimensional ribbon along the a axis through C—H···π interactions. Intermolecular interactions are shown as dashed lines and H atoms not involved in these interactions have been omitted for clarity. Ring centroids are indicated with solid circles. [Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+1, -y, -z+1; (iii) x-1, y, z.]
[Figure 8] Fig. 8. A partial packing diagram for (II), showing the centrosymmetric ππ dimers (A···A and B···B) linked by C—H···π into a one-dimensional chain diagonally along the ab plane. A C—H···O interaction links the parallel chains and forms a two-dimensional network. Intermolecular interactions are shown as dashed lines and H atoms not involved in these interactions have been omitted for clarity. Ring centroids are indicated with solid circles. [Symmetry codes: (i) x-1, y+1, z; (ii) -x+2, -y+1, -z+1; (iii) -x, -y+2, -z+2.]
[Figure 9] Fig. 9. Packing diagram for (III), showing the cyclic tetramer formation through the combination of ππ and C—H···π interactions. The extension of tetramer into a one-dimensional ribbon by C—H···O and into a two-dimensional network by C—H···π interactions is illustrated. Intermolecular interactions are shown as dashed lines and H atoms not involved in these interactions have been omitted for clarity. Ring centroids are indicated with solid circles. [Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x+1, y, z; (iii) x, y, z; (iv) -x+1, -y+2, -z+1.]
[Figure 10] Fig. 10. Packing diagram for (IV), showing C—H···O dimers (A···A and B···B), the propagation of dimers of molecule A into a one-dimensional ribbon and the bridging role of the molecule B dimer between two parallel one-dimensional ribbons. Intermolecular interactions are shown as dashed lines and H atoms not involved in these interactions have been omitted for clarity. Ring centroids are indicated with solid circles. [Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+2, -y+2, -z+1; (iii) x, y, z+1; (iv) x, y, z+1; (v) -x+1, -y+2, -z+1.]
(I) 1,1''-Dibenzyl-5'-(4-chlorophenyl)-4'-phenyl-4',5'-dihydrodispiro[indoline-3,2'-furan-3',3''-indoline]-2,2''-dione top
Crystal data top
C44H33ClN2O3F(000) = 704
Mr = 673.17Dx = 1.311 Mg m3
Triclinic, P1Melting point: 462 K
a = 10.1099 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.3367 (11) ÅCell parameters from 6765 reflections
c = 17.0315 (17) Åθ = 2.2–28.1°
α = 74.755 (2)°µ = 0.16 mm1
β = 78.503 (2)°T = 294 K
γ = 65.557 (2)°Block, colorless
V = 1705.4 (3) Å30.15 × 0.08 × 0.06 mm
Z = 2
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
6578 reflections with I > 2σ(I)
ω scansRint = 0.020
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
θmax = 28.3°, θmin = 2.0°
Tmin = 0.92, Tmax = 0.98h = 1313
20091 measured reflectionsk = 1514
8008 independent reflectionsl = 2222
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.155 w = 1/[σ2(Fo2) + (0.0604P)2 + 0.5199P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.001
8008 reflectionsΔρmax = 0.32 e Å3
451 parametersΔρmin = 0.17 e Å3
Crystal data top
C44H33ClN2O3γ = 65.557 (2)°
Mr = 673.17V = 1705.4 (3) Å3
Triclinic, P1Z = 2
a = 10.1099 (10) ÅMo Kα radiation
b = 11.3367 (11) ŵ = 0.16 mm1
c = 17.0315 (17) ÅT = 294 K
α = 74.755 (2)°0.15 × 0.08 × 0.06 mm
β = 78.503 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
8008 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
6578 reflections with I > 2σ(I)
Tmin = 0.92, Tmax = 0.98Rint = 0.020
20091 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.155H-atom parameters constrained
S = 1.13Δρmax = 0.32 e Å3
8008 reflectionsΔρmin = 0.17 e Å3
451 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7853 (2)0.98539 (19)0.56546 (10)0.0424 (4)
C20.7003 (2)0.9799 (2)0.51362 (12)0.0510 (5)
H20.62441.05520.49130.061*
C30.7325 (2)0.8577 (2)0.49614 (13)0.0568 (5)
H30.67680.85070.46150.068*
C40.8448 (2)0.7467 (2)0.52889 (13)0.0571 (5)
H40.86660.66670.51430.069*
C50.9262 (2)0.7524 (2)0.58334 (12)0.0491 (4)
H51.00130.67680.60610.059*
C60.89358 (19)0.87246 (19)0.60296 (10)0.0401 (4)
C70.97125 (18)0.91257 (18)0.65156 (10)0.0390 (4)
C80.9074 (2)1.06524 (19)0.62420 (10)0.0426 (4)
C91.19816 (19)0.86550 (19)0.68953 (10)0.0415 (4)
H91.20040.95400.67860.050*
C101.10768 (19)0.84000 (19)0.77221 (10)0.0419 (4)
H101.14820.74410.79250.050*
C110.95038 (19)0.87418 (18)0.74903 (10)0.0392 (4)
C120.81795 (19)0.9682 (2)0.79171 (10)0.0430 (4)
C130.7773 (2)1.0974 (2)0.79902 (12)0.0534 (5)
H130.83731.14360.77430.064*
C140.6456 (3)1.1576 (3)0.84378 (13)0.0652 (6)
H140.61801.24460.84870.078*
C150.5558 (3)1.0909 (3)0.88073 (14)0.0709 (7)
H150.46781.13360.90980.085*
C160.5944 (2)0.9617 (3)0.87530 (13)0.0646 (6)
H160.53430.91580.90060.077*
C170.7259 (2)0.9020 (2)0.83089 (11)0.0491 (5)
C180.9219 (2)0.7450 (2)0.77491 (11)0.0458 (4)
C191.1263 (2)0.9000 (2)0.83660 (12)0.0525 (5)
C201.1195 (3)1.0282 (3)0.82109 (16)0.0700 (7)
H201.09621.08310.77040.084*
C211.1474 (3)1.0756 (4)0.8810 (2)0.0936 (10)
H211.14221.16210.87030.112*
C221.1825 (3)0.9950 (5)0.9559 (2)0.1032 (12)
H221.20101.02700.99580.124*
C231.1900 (3)0.8687 (4)0.97173 (18)0.1010 (11)
H231.21460.81421.02230.121*
C241.1612 (3)0.8206 (3)0.91275 (14)0.0731 (7)
H241.16530.73440.92440.088*
C251.35044 (19)0.76256 (19)0.68628 (10)0.0415 (4)
C261.4692 (2)0.7934 (2)0.68647 (12)0.0497 (5)
H261.45510.87990.68620.060*
C271.6089 (2)0.6964 (2)0.68711 (13)0.0568 (5)
H271.68860.71760.68680.068*
C281.6286 (2)0.5690 (2)0.68822 (13)0.0555 (5)
C291.5125 (2)0.5354 (2)0.68768 (13)0.0541 (5)
H291.52730.44860.68810.065*
C301.3740 (2)0.6329 (2)0.68652 (11)0.0480 (4)
H301.29500.61130.68590.058*
C310.6959 (2)1.2332 (2)0.55049 (12)0.0511 (5)
H31A0.70211.24480.49160.061*
H31B0.73231.29330.56180.061*
C320.5377 (2)1.26988 (19)0.58486 (11)0.0465 (4)
C330.4951 (2)1.2084 (2)0.66118 (13)0.0602 (5)
H330.56441.13720.69140.072*
C340.3508 (3)1.2519 (3)0.69286 (16)0.0778 (7)
H340.32331.20950.74420.093*
C350.2464 (3)1.3579 (3)0.64899 (19)0.0786 (8)
H350.14941.38840.67120.094*
C360.2868 (3)1.4174 (2)0.57281 (17)0.0676 (6)
H360.21691.48810.54270.081*
C370.4307 (2)1.3732 (2)0.54047 (14)0.0556 (5)
H370.45671.41320.48800.067*
C380.7306 (3)0.6702 (3)0.86056 (14)0.0673 (6)
H38A0.78720.59070.83880.081*
H38B0.63070.70050.84840.081*
C390.7333 (3)0.6362 (2)0.95236 (13)0.0590 (5)
C400.8370 (3)0.6445 (3)0.98913 (15)0.0720 (7)
H400.90660.67550.95740.086*
C410.8387 (4)0.6067 (3)1.07362 (17)0.0852 (8)
H410.90940.61261.09820.102*
C420.7373 (4)0.5613 (3)1.12024 (17)0.0889 (10)
H420.73870.53611.17670.107*
C430.6335 (4)0.5524 (3)1.08463 (18)0.0904 (9)
H430.56490.52041.11680.108*
C440.6299 (3)0.5909 (3)1.00097 (16)0.0764 (7)
H440.55750.58630.97710.092*
Cl11.80351 (7)0.44690 (8)0.68860 (6)0.0992 (3)
N10.78866 (17)1.09873 (15)0.58347 (9)0.0450 (4)
N20.78804 (19)0.77128 (18)0.81948 (10)0.0524 (4)
O10.95298 (16)1.14096 (14)0.63705 (9)0.0537 (3)
O21.12322 (13)0.85615 (13)0.62992 (7)0.0430 (3)
O31.00378 (17)0.63808 (15)0.76013 (9)0.0584 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0431 (9)0.0532 (11)0.0321 (8)0.0220 (8)0.0014 (7)0.0086 (7)
C20.0475 (11)0.0659 (13)0.0399 (10)0.0233 (10)0.0097 (8)0.0047 (9)
C30.0597 (13)0.0791 (15)0.0455 (11)0.0356 (12)0.0110 (9)0.0159 (10)
C40.0656 (13)0.0653 (13)0.0531 (12)0.0312 (11)0.0058 (10)0.0225 (10)
C50.0475 (10)0.0555 (12)0.0463 (10)0.0198 (9)0.0034 (8)0.0143 (9)
C60.0394 (9)0.0535 (11)0.0304 (8)0.0219 (8)0.0007 (7)0.0100 (7)
C70.0372 (9)0.0512 (10)0.0302 (8)0.0193 (8)0.0006 (7)0.0100 (7)
C80.0445 (10)0.0544 (11)0.0316 (8)0.0235 (9)0.0041 (7)0.0113 (8)
C90.0406 (9)0.0542 (11)0.0356 (9)0.0230 (8)0.0011 (7)0.0127 (8)
C100.0386 (9)0.0553 (11)0.0334 (9)0.0192 (8)0.0014 (7)0.0113 (8)
C110.0396 (9)0.0515 (10)0.0298 (8)0.0206 (8)0.0019 (7)0.0093 (7)
C120.0392 (9)0.0591 (11)0.0302 (8)0.0179 (8)0.0026 (7)0.0102 (8)
C130.0554 (12)0.0621 (13)0.0422 (10)0.0187 (10)0.0042 (9)0.0167 (9)
C140.0631 (14)0.0719 (15)0.0475 (12)0.0067 (12)0.0049 (10)0.0232 (11)
C150.0472 (12)0.0950 (19)0.0461 (12)0.0049 (12)0.0036 (10)0.0179 (12)
C160.0446 (11)0.0945 (19)0.0443 (11)0.0250 (12)0.0038 (9)0.0063 (11)
C170.0432 (10)0.0686 (13)0.0337 (9)0.0227 (9)0.0026 (7)0.0064 (8)
C180.0510 (11)0.0589 (12)0.0325 (9)0.0272 (10)0.0057 (8)0.0061 (8)
C190.0407 (10)0.0829 (15)0.0418 (10)0.0255 (10)0.0005 (8)0.0258 (10)
C200.0709 (15)0.0964 (19)0.0645 (14)0.0460 (14)0.0071 (12)0.0390 (13)
C210.0862 (19)0.138 (3)0.097 (2)0.066 (2)0.0178 (17)0.072 (2)
C220.083 (2)0.180 (4)0.079 (2)0.054 (2)0.0011 (16)0.080 (2)
C230.088 (2)0.162 (3)0.0582 (16)0.033 (2)0.0182 (14)0.0454 (19)
C240.0630 (14)0.109 (2)0.0450 (12)0.0238 (14)0.0088 (10)0.0243 (12)
C250.0406 (9)0.0590 (11)0.0296 (8)0.0237 (8)0.0004 (7)0.0122 (7)
C260.0470 (10)0.0613 (12)0.0488 (11)0.0274 (9)0.0021 (8)0.0148 (9)
C270.0428 (11)0.0782 (15)0.0552 (12)0.0288 (10)0.0054 (9)0.0131 (11)
C280.0417 (10)0.0682 (14)0.0483 (11)0.0127 (10)0.0042 (8)0.0122 (10)
C290.0579 (12)0.0554 (12)0.0494 (11)0.0204 (10)0.0024 (9)0.0157 (9)
C300.0465 (10)0.0619 (12)0.0435 (10)0.0275 (9)0.0026 (8)0.0139 (9)
C310.0573 (12)0.0505 (11)0.0402 (10)0.0195 (9)0.0038 (9)0.0030 (8)
C320.0537 (11)0.0479 (11)0.0418 (10)0.0190 (9)0.0085 (8)0.0138 (8)
C330.0550 (12)0.0776 (15)0.0439 (11)0.0228 (11)0.0067 (9)0.0086 (10)
C340.0627 (15)0.113 (2)0.0576 (14)0.0375 (15)0.0054 (12)0.0198 (14)
C350.0482 (13)0.098 (2)0.095 (2)0.0211 (13)0.0013 (13)0.0426 (17)
C360.0591 (14)0.0591 (14)0.0866 (18)0.0118 (11)0.0220 (13)0.0248 (13)
C370.0667 (14)0.0487 (11)0.0566 (12)0.0219 (10)0.0162 (10)0.0122 (9)
C380.0784 (16)0.0913 (18)0.0509 (12)0.0587 (14)0.0035 (11)0.0036 (11)
C390.0668 (14)0.0601 (13)0.0486 (11)0.0296 (11)0.0022 (10)0.0057 (10)
C400.0768 (16)0.0834 (17)0.0564 (14)0.0349 (14)0.0057 (12)0.0085 (12)
C410.103 (2)0.0760 (18)0.0642 (16)0.0161 (16)0.0228 (16)0.0136 (13)
C420.126 (3)0.0601 (16)0.0488 (14)0.0142 (16)0.0049 (16)0.0046 (12)
C430.111 (2)0.0765 (18)0.0643 (17)0.0380 (18)0.0261 (17)0.0052 (14)
C440.0867 (18)0.0753 (16)0.0647 (15)0.0430 (15)0.0129 (13)0.0054 (12)
Cl10.0510 (4)0.0867 (5)0.1342 (7)0.0032 (3)0.0095 (4)0.0188 (5)
N10.0481 (9)0.0479 (9)0.0379 (8)0.0186 (7)0.0049 (7)0.0059 (7)
N20.0540 (10)0.0692 (11)0.0401 (8)0.0357 (9)0.0009 (7)0.0049 (8)
O10.0594 (8)0.0579 (8)0.0537 (8)0.0321 (7)0.0016 (6)0.0141 (6)
O20.0372 (6)0.0621 (8)0.0319 (6)0.0206 (6)0.0001 (5)0.0134 (5)
O30.0706 (10)0.0536 (9)0.0530 (8)0.0264 (8)0.0027 (7)0.0124 (7)
Geometric parameters (Å, º) top
C1—C21.377 (3)C22—H220.9300
C1—C61.391 (3)C23—C241.388 (4)
C1—N11.412 (2)C23—H230.9300
C2—C31.386 (3)C24—H240.9300
C2—H20.9300C25—C261.383 (3)
C3—C41.373 (3)C25—C301.388 (3)
C3—H30.9300C26—C271.386 (3)
C4—C51.386 (3)C26—H260.9300
C4—H40.9300C27—C281.369 (3)
C5—C61.377 (3)C27—H270.9300
C5—H50.9300C28—C291.378 (3)
C6—C71.504 (2)C28—Cl11.737 (2)
C7—O21.411 (2)C29—C301.379 (3)
C7—C81.549 (3)C29—H290.9300
C7—C111.596 (2)C30—H300.9300
C8—O11.210 (2)C31—N11.447 (2)
C8—N11.372 (2)C31—C321.509 (3)
C9—O21.430 (2)C31—H31A0.9700
C9—C251.499 (3)C31—H31B0.9700
C9—C101.547 (2)C32—C331.382 (3)
C9—H90.9800C32—C371.388 (3)
C10—C191.511 (3)C33—C341.376 (3)
C10—C111.580 (2)C33—H330.9300
C10—H100.9800C34—C351.382 (4)
C11—C121.515 (2)C34—H340.9300
C11—C181.543 (3)C35—C361.365 (4)
C12—C131.380 (3)C35—H350.9300
C12—C171.394 (3)C36—C371.376 (3)
C13—C141.392 (3)C36—H360.9300
C13—H130.9300C37—H370.9300
C14—C151.371 (4)C38—N21.451 (3)
C14—H140.9300C38—C391.512 (3)
C15—C161.375 (4)C38—H38A0.9700
C15—H150.9300C38—H38B0.9700
C16—C171.386 (3)C39—C401.369 (3)
C16—H160.9300C39—C441.385 (3)
C17—N21.401 (3)C40—C411.391 (4)
C18—O31.211 (2)C40—H400.9300
C18—N21.368 (2)C41—C421.359 (5)
C19—C201.382 (3)C41—H410.9300
C19—C241.387 (3)C42—C431.360 (5)
C20—C211.392 (3)C42—H420.9300
C20—H200.9300C43—C441.379 (4)
C21—C221.374 (5)C43—H430.9300
C21—H210.9300C44—H440.9300
C22—C231.358 (5)
C2—C1—C6121.94 (18)C22—C23—H23119.8
C2—C1—N1128.07 (18)C24—C23—H23119.8
C6—C1—N1109.76 (15)C19—C24—C23120.6 (3)
C1—C2—C3117.25 (19)C19—C24—H24119.7
C1—C2—H2121.4C23—C24—H24119.7
C3—C2—H2121.4C26—C25—C30118.76 (18)
C4—C3—C2121.36 (18)C26—C25—C9120.89 (17)
C4—C3—H3119.3C30—C25—C9120.29 (16)
C2—C3—H3119.3C25—C26—C27120.5 (2)
C3—C4—C5120.9 (2)C25—C26—H26119.7
C3—C4—H4119.6C27—C26—H26119.7
C5—C4—H4119.6C28—C27—C26119.40 (19)
C6—C5—C4118.54 (19)C28—C27—H27120.3
C6—C5—H5120.7C26—C27—H27120.3
C4—C5—H5120.7C27—C28—C29121.41 (19)
C5—C6—C1119.81 (17)C27—C28—Cl1119.69 (17)
C5—C6—C7130.70 (17)C29—C28—Cl1118.89 (18)
C1—C6—C7108.81 (16)C28—C29—C30118.7 (2)
O2—C7—C6109.39 (13)C28—C29—H29120.7
O2—C7—C8112.61 (14)C30—C29—H29120.7
C6—C7—C8101.82 (14)C29—C30—C25121.21 (18)
O2—C7—C11105.24 (13)C29—C30—H30119.4
C6—C7—C11118.86 (14)C25—C30—H30119.4
C8—C7—C11109.14 (13)N1—C31—C32113.69 (16)
O1—C8—N1126.35 (19)N1—C31—H31A108.8
O1—C8—C7126.35 (17)C32—C31—H31A108.8
N1—C8—C7107.30 (15)N1—C31—H31B108.8
O2—C9—C25108.44 (14)C32—C31—H31B108.8
O2—C9—C10104.79 (13)H31A—C31—H31B107.7
C25—C9—C10112.21 (15)C33—C32—C37118.2 (2)
O2—C9—H9110.4C33—C32—C31122.41 (18)
C25—C9—H9110.4C37—C32—C31119.34 (18)
C10—C9—H9110.4C34—C33—C32120.5 (2)
C19—C10—C9113.09 (15)C34—C33—H33119.7
C19—C10—C11120.40 (15)C32—C33—H33119.7
C9—C10—C11104.92 (13)C33—C34—C35120.5 (2)
C19—C10—H10105.8C33—C34—H34119.7
C9—C10—H10105.8C35—C34—H34119.7
C11—C10—H10105.8C36—C35—C34119.5 (2)
C12—C11—C18102.01 (14)C36—C35—H35120.3
C12—C11—C10119.47 (14)C34—C35—H35120.3
C18—C11—C10107.05 (15)C35—C36—C37120.2 (2)
C12—C11—C7116.58 (14)C35—C36—H36119.9
C18—C11—C7109.11 (13)C37—C36—H36119.9
C10—C11—C7102.16 (13)C36—C37—C32121.1 (2)
C13—C12—C17118.41 (18)C36—C37—H37119.5
C13—C12—C11133.17 (17)C32—C37—H37119.5
C17—C12—C11108.41 (17)N2—C38—C39113.68 (19)
C12—C13—C14119.2 (2)N2—C38—H38A108.8
C12—C13—H13120.4C39—C38—H38A108.8
C14—C13—H13120.4N2—C38—H38B108.8
C15—C14—C13121.3 (2)C39—C38—H38B108.8
C15—C14—H14119.4H38A—C38—H38B107.7
C13—C14—H14119.4C40—C39—C44118.7 (2)
C14—C15—C16120.7 (2)C40—C39—C38122.4 (2)
C14—C15—H15119.6C44—C39—C38118.8 (2)
C16—C15—H15119.6C39—C40—C41120.4 (3)
C15—C16—C17117.8 (2)C39—C40—H40119.8
C15—C16—H16121.1C41—C40—H40119.8
C17—C16—H16121.1C42—C41—C40120.1 (3)
C16—C17—C12122.6 (2)C42—C41—H41120.0
C16—C17—N2127.3 (2)C40—C41—H41120.0
C12—C17—N2110.12 (17)C41—C42—C43120.3 (3)
O3—C18—N2125.42 (19)C41—C42—H42119.9
O3—C18—C11126.54 (17)C43—C42—H42119.9
N2—C18—C11108.02 (17)C42—C43—C44120.1 (3)
C20—C19—C24118.5 (2)C42—C43—H43119.9
C20—C19—C10122.68 (19)C44—C43—H43119.9
C24—C19—C10118.6 (2)C43—C44—C39120.4 (3)
C19—C20—C21120.3 (3)C43—C44—H44119.8
C19—C20—H20119.9C39—C44—H44119.8
C21—C20—H20119.9C8—N1—C1110.56 (16)
C22—C21—C20120.2 (3)C8—N1—C31124.31 (17)
C22—C21—H21119.9C1—N1—C31124.22 (16)
C20—C21—H21119.9C18—N2—C17111.27 (16)
C23—C22—C21120.0 (3)C18—N2—C38123.5 (2)
C23—C22—H22120.0C17—N2—C38124.50 (18)
C21—C22—H22120.0C7—O2—C9109.18 (12)
C22—C23—C24120.3 (3)
C6—C1—C2—C33.7 (3)C11—C10—C19—C24105.9 (2)
N1—C1—C2—C3170.20 (18)C24—C19—C20—C210.0 (3)
C1—C2—C3—C40.3 (3)C10—C19—C20—C21175.6 (2)
C2—C3—C4—C52.6 (3)C19—C20—C21—C220.3 (4)
C3—C4—C5—C61.0 (3)C20—C21—C22—C230.0 (5)
C4—C5—C6—C12.8 (3)C21—C22—C23—C240.6 (5)
C4—C5—C6—C7172.29 (18)C20—C19—C24—C230.6 (4)
C2—C1—C6—C55.4 (3)C10—C19—C24—C23175.2 (2)
N1—C1—C6—C5169.57 (16)C22—C23—C24—C190.9 (4)
C2—C1—C6—C7176.93 (16)O2—C9—C25—C26134.44 (17)
N1—C1—C6—C72.00 (19)C10—C9—C25—C26110.30 (19)
C5—C6—C7—O242.1 (2)O2—C9—C25—C3048.3 (2)
C1—C6—C7—O2128.21 (15)C10—C9—C25—C3067.0 (2)
C5—C6—C7—C8161.46 (18)C30—C25—C26—C270.2 (3)
C1—C6—C7—C88.87 (17)C9—C25—C26—C27177.13 (17)
C5—C6—C7—C1178.7 (2)C25—C26—C27—C280.5 (3)
C1—C6—C7—C11110.99 (17)C26—C27—C28—C290.8 (3)
O2—C7—C8—O150.7 (2)C26—C27—C28—Cl1179.73 (16)
C6—C7—C8—O1167.75 (17)C27—C28—C29—C300.4 (3)
C11—C7—C8—O165.8 (2)Cl1—C28—C29—C30179.34 (16)
O2—C7—C8—N1129.95 (15)C28—C29—C30—C250.3 (3)
C6—C7—C8—N112.92 (17)C26—C25—C30—C290.6 (3)
C11—C7—C8—N1113.57 (15)C9—C25—C30—C29176.74 (17)
O2—C9—C10—C19155.55 (16)N1—C31—C32—C3325.9 (3)
C25—C9—C10—C1987.0 (2)N1—C31—C32—C37157.26 (17)
O2—C9—C10—C1122.48 (18)C37—C32—C33—C342.0 (3)
C25—C9—C10—C11139.94 (15)C31—C32—C33—C34174.9 (2)
C19—C10—C11—C120.2 (3)C32—C33—C34—C350.2 (4)
C9—C10—C11—C12128.60 (17)C33—C34—C35—C361.7 (4)
C19—C10—C11—C18114.82 (19)C34—C35—C36—C370.8 (4)
C9—C10—C11—C18116.35 (15)C35—C36—C37—C321.4 (3)
C19—C10—C11—C7130.58 (17)C33—C32—C37—C362.8 (3)
C9—C10—C11—C71.75 (18)C31—C32—C37—C36174.13 (19)
O2—C7—C11—C12151.95 (15)N2—C38—C39—C4030.5 (4)
C6—C7—C11—C1285.2 (2)N2—C38—C39—C44151.6 (2)
C8—C7—C11—C1230.9 (2)C44—C39—C40—C410.6 (4)
O2—C7—C11—C1893.24 (16)C38—C39—C40—C41177.3 (2)
C6—C7—C11—C1829.6 (2)C39—C40—C41—C420.0 (4)
C8—C7—C11—C18145.68 (15)C40—C41—C42—C430.0 (4)
O2—C7—C11—C1019.84 (17)C41—C42—C43—C440.6 (5)
C6—C7—C11—C10142.73 (16)C42—C43—C44—C391.3 (4)
C8—C7—C11—C10101.24 (16)C40—C39—C44—C431.3 (4)
C18—C11—C12—C13175.4 (2)C38—C39—C44—C43176.7 (3)
C10—C11—C12—C1357.8 (3)O1—C8—N1—C1168.04 (17)
C7—C11—C12—C1365.8 (3)C7—C8—N1—C112.62 (18)
C18—C11—C12—C173.32 (18)O1—C8—N1—C311.4 (3)
C10—C11—C12—C17120.99 (17)C7—C8—N1—C31177.92 (15)
C7—C11—C12—C17115.41 (17)C2—C1—N1—C8167.52 (18)
C17—C12—C13—C141.1 (3)C6—C1—N1—C87.0 (2)
C11—C12—C13—C14179.73 (19)C2—C1—N1—C311.9 (3)
C12—C13—C14—C150.1 (3)C6—C1—N1—C31176.48 (16)
C13—C14—C15—C160.7 (4)C32—C31—N1—C8121.08 (19)
C14—C15—C16—C170.5 (3)C32—C31—N1—C170.9 (2)
C15—C16—C17—C120.5 (3)O3—C18—N2—C17175.25 (18)
C15—C16—C17—N2178.0 (2)C11—C18—N2—C173.4 (2)
C13—C12—C17—C161.3 (3)O3—C18—N2—C384.7 (3)
C11—C12—C17—C16179.71 (17)C11—C18—N2—C38173.96 (17)
C13—C12—C17—N2177.45 (16)C16—C17—N2—C18177.42 (19)
C11—C12—C17—N21.5 (2)C12—C17—N2—C181.3 (2)
C12—C11—C18—O3174.62 (18)C16—C17—N2—C387.0 (3)
C10—C11—C18—O348.4 (2)C12—C17—N2—C38171.68 (18)
C7—C11—C18—O361.5 (2)C39—C38—N2—C18105.6 (2)
C12—C11—C18—N24.06 (18)C39—C38—N2—C1763.7 (3)
C10—C11—C18—N2130.31 (15)C6—C7—O2—C9165.41 (14)
C7—C11—C18—N2119.85 (16)C8—C7—O2—C982.15 (16)
C9—C10—C19—C2046.6 (3)C11—C7—O2—C936.64 (17)
C11—C10—C19—C2078.5 (2)C25—C9—O2—C7157.84 (14)
C9—C10—C19—C24129.0 (2)C10—C9—O2—C737.83 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O30.932.553.067 (2)116
C9—H9···O10.982.603.115 (2)113
C10—H10···O30.982.452.951 (2)111
C13—H13···O10.932.403.011 (3)123
C31—H31B···O10.972.532.914 (3)104
C38—H38A···O30.972.512.881 (3)103
C31—H31A···O2i0.972.613.417 (2)141
C3—H3···Cg1(C32–C37)ii0.932.903.734 (2)149
C27—H27···Cg2(C1–C6)iii0.932.913.537 (2)126
C33—H33···Cg3(C12–C17)0.932.903.560 (2)147
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+1, y+2, z+1; (iii) x+1, y, z.
(II) 1''-Acetyl-1-benzyl-5'-(4-chlorophenyl)-4'-phenyl-4',5'-dihydrodispiro[indoline-3,2'-furan-3',3''-indoline]-2,2''-dione top
Crystal data top
C39H29ClN2O4F(000) = 1304
Mr = 625.09Dx = 1.335 Mg m3
Triclinic, P1Melting point: 430 K
a = 11.9830 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.9260 (6) ÅCell parameters from 6374 reflections
c = 21.5664 (10) Åθ = 2.2–21.4°
α = 76.330 (1)°µ = 0.17 mm1
β = 76.522 (1)°T = 294 K
γ = 77.553 (1)°Block, colorless
V = 3110.6 (2) Å30.13 × 0.11 × 0.06 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
8962 reflections with I > 2σ(I)
ω scansRint = 0.034
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
θmax = 28.3°, θmin = 1.7°
Tmin = 0.94, Tmax = 0.97h = 1516
36879 measured reflectionsk = 1716
14644 independent reflectionsl = 2828
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.160 w = 1/[σ2(Fo2) + (0.0634P)2 + 0.627P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
14644 reflectionsΔρmax = 0.27 e Å3
831 parametersΔρmin = 0.19 e Å3
Crystal data top
C39H29ClN2O4γ = 77.553 (1)°
Mr = 625.09V = 3110.6 (2) Å3
Triclinic, P1Z = 4
a = 11.9830 (5) ÅMo Kα radiation
b = 12.9260 (6) ŵ = 0.17 mm1
c = 21.5664 (10) ÅT = 294 K
α = 76.330 (1)°0.13 × 0.11 × 0.06 mm
β = 76.522 (1)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
14644 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
8962 reflections with I > 2σ(I)
Tmin = 0.94, Tmax = 0.97Rint = 0.034
36879 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.160H-atom parameters constrained
S = 1.04Δρmax = 0.27 e Å3
14644 reflectionsΔρmin = 0.19 e Å3
831 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1A0.8810 (2)0.62529 (18)0.51557 (11)0.0474 (5)
C2A0.8838 (2)0.6694 (2)0.45087 (12)0.0608 (7)
H2A0.83030.65870.42890.073*
C3A0.9694 (3)0.7303 (2)0.41976 (14)0.0707 (8)
H3A0.97270.76240.37610.085*
C4A1.0502 (2)0.7448 (2)0.45157 (14)0.0657 (7)
H4A1.10920.78340.42890.079*
C5A1.0441 (2)0.70198 (18)0.51732 (13)0.0542 (6)
H5A1.09770.71270.53920.065*
C6A0.95706 (18)0.64318 (17)0.54974 (11)0.0448 (5)
C7A0.93126 (18)0.58280 (17)0.61892 (11)0.0420 (5)
C8A0.84016 (18)0.51592 (17)0.61534 (11)0.0437 (5)
C9A1.01708 (19)0.48447 (18)0.70616 (11)0.0472 (6)
H9A0.98090.41950.72010.057*
C10A0.93328 (18)0.57950 (17)0.73395 (11)0.0450 (5)
H10A0.98320.62190.74390.054*
C11A0.88082 (18)0.65210 (16)0.67438 (10)0.0409 (5)
C12A0.75275 (18)0.69908 (18)0.67860 (11)0.0442 (5)
C13A0.65389 (19)0.6531 (2)0.70518 (11)0.0529 (6)
H13A0.65970.58060.72540.063*
C14A0.5460 (2)0.7169 (2)0.70113 (13)0.0618 (7)
H14A0.47880.68740.71980.074*
C15A0.5371 (2)0.8228 (3)0.66991 (14)0.0679 (8)
H15A0.46370.86370.66750.081*
C16A0.6343 (2)0.8705 (2)0.64199 (14)0.0638 (7)
H16A0.62780.94230.62040.077*
C17A0.7415 (2)0.80706 (19)0.64754 (11)0.0488 (6)
C18A0.9361 (2)0.75484 (17)0.65129 (11)0.0450 (5)
C19A0.85210 (19)0.5456 (2)0.79726 (12)0.0515 (6)
C20A0.7863 (2)0.4650 (2)0.80723 (13)0.0664 (7)
H20A0.79040.42990.77350.080*
C21A0.7146 (3)0.4360 (3)0.86644 (16)0.0829 (10)
H21A0.67010.38260.87220.099*
C22A0.7090 (3)0.4862 (3)0.91689 (16)0.0930 (11)
H22A0.66080.46660.95680.112*
C23A0.7740 (3)0.5648 (3)0.90844 (16)0.0874 (10)
H23A0.77080.59840.94260.105*
C24A0.8449 (2)0.5945 (2)0.84884 (13)0.0660 (7)
H24A0.88860.64850.84340.079*
C25A1.13691 (19)0.45898 (18)0.72273 (11)0.0484 (6)
C26A1.1771 (2)0.36208 (19)0.75998 (12)0.0556 (6)
H26A1.12860.31070.77660.067*
C27A1.2882 (2)0.3395 (2)0.77329 (13)0.0636 (7)
H27A1.31390.27390.79890.076*
C28A1.3596 (2)0.4148 (2)0.74830 (13)0.0589 (7)
C29A1.3224 (2)0.5117 (2)0.71085 (14)0.0680 (7)
H29A1.37170.56240.69400.082*
C30A1.2114 (2)0.5337 (2)0.69832 (14)0.0650 (7)
H30A1.18590.59980.67310.078*
C31A0.7317 (2)0.5043 (2)0.53220 (14)0.0600 (7)
H31A0.70470.44590.56600.072*
H31B0.77590.47320.49520.072*
C32A0.6275 (2)0.58260 (19)0.51220 (12)0.0516 (6)
C33A0.5586 (3)0.6489 (2)0.55204 (15)0.0765 (8)
H33A0.57810.64840.59140.092*
C34A0.4608 (3)0.7162 (3)0.53455 (18)0.0929 (10)
H34A0.41460.76070.56220.112*
C35A0.4306 (3)0.7184 (3)0.47683 (18)0.0836 (9)
H35A0.36420.76400.46520.100*
C36A0.4990 (3)0.6531 (3)0.43672 (15)0.0734 (8)
H36A0.47940.65430.39730.088*
C37A0.5970 (2)0.5853 (2)0.45399 (13)0.0624 (7)
H37A0.64300.54100.42620.075*
C38A0.8748 (3)0.9421 (2)0.59184 (13)0.0638 (7)
C39A0.9931 (3)0.9685 (2)0.58453 (16)0.0804 (9)
H39A0.99741.03850.55720.121*
H39B1.05070.91530.56510.121*
H39C1.00720.96880.62650.121*
Cl1A1.50042 (6)0.38930 (7)0.76315 (5)0.0968 (3)
N1A0.80898 (16)0.55230 (15)0.55602 (9)0.0488 (5)
N2A0.85284 (16)0.84018 (14)0.62867 (9)0.0489 (5)
O1A0.80457 (14)0.44398 (13)0.65754 (8)0.0564 (4)
O2A1.03345 (12)0.51722 (12)0.63662 (7)0.0482 (4)
O3A1.03435 (14)0.76046 (12)0.65277 (9)0.0587 (4)
O4A0.79804 (19)1.00424 (16)0.56870 (11)0.0931 (7)
C1B0.1285 (2)0.8710 (2)0.99801 (12)0.0544 (6)
C2B0.1175 (2)0.8145 (2)1.06129 (13)0.0723 (8)
H2B0.15520.82871.09070.087*
C3B0.0485 (3)0.7365 (3)1.07879 (17)0.0890 (10)
H3B0.04080.69581.12080.107*
C4B0.0094 (3)0.7168 (3)1.03644 (18)0.0924 (11)
H4B0.05770.66511.05060.111*
C5B0.0030 (2)0.7731 (2)0.97250 (15)0.0716 (8)
H5B0.03630.75960.94360.086*
C6B0.07510 (19)0.84921 (19)0.95315 (12)0.0514 (6)
C8B0.16716 (18)1.00184 (19)0.90820 (12)0.0462 (5)
C7B0.10357 (18)0.92456 (18)0.88946 (11)0.0445 (5)
C9B0.03217 (18)1.02835 (18)0.79990 (11)0.0462 (5)
H9B0.06131.09500.79700.055*
C10B0.13107 (17)0.94606 (17)0.77017 (11)0.0430 (5)
H10B0.09270.89860.75580.052*
C11B0.18419 (18)0.87469 (17)0.82947 (11)0.0442 (5)
C12B0.31239 (18)0.85458 (19)0.83126 (11)0.0461 (5)
C13B0.39071 (19)0.9242 (2)0.81823 (12)0.0558 (6)
H13B0.36780.99780.80370.067*
C14B0.5039 (2)0.8837 (3)0.82698 (13)0.0696 (8)
H14B0.55680.93070.81860.083*
C15B0.5392 (2)0.7755 (3)0.84773 (14)0.0778 (9)
H15B0.61590.75020.85290.093*
C16B0.4635 (2)0.7034 (3)0.86102 (13)0.0713 (8)
H16B0.48730.62990.87530.086*
C17B0.3498 (2)0.7447 (2)0.85224 (11)0.0534 (6)
C18B0.1613 (2)0.75917 (19)0.83921 (12)0.0519 (6)
C19B0.20961 (18)0.99593 (19)0.70979 (12)0.0489 (6)
C20B0.2531 (2)1.0889 (2)0.70607 (14)0.0632 (7)
H20B0.23871.11940.74270.076*
C21B0.3172 (2)1.1365 (3)0.64903 (17)0.0826 (10)
H21B0.34731.19770.64770.099*
C22B0.3369 (3)1.0942 (3)0.59424 (18)0.0938 (12)
H22B0.37881.12760.55550.113*
C23B0.2947 (3)1.0023 (3)0.59645 (15)0.0875 (10)
H23B0.30810.97330.55930.105*
C24B0.2318 (2)0.9528 (2)0.65447 (13)0.0630 (7)
H24B0.20440.89000.65610.076*
C25B0.07591 (18)1.05487 (18)0.77123 (11)0.0436 (5)
C26B0.1233 (2)1.16007 (19)0.74854 (12)0.0522 (6)
H26B0.08621.21560.74980.063*
C27B0.2248 (2)1.1850 (2)0.72392 (12)0.0581 (6)
H27B0.25541.25650.70830.070*
C28B0.27922 (19)1.1030 (2)0.72300 (11)0.0512 (6)
C29B0.23372 (19)0.99666 (19)0.74473 (12)0.0508 (6)
H29B0.27080.94150.74290.061*
C30B0.13283 (18)0.97298 (18)0.76913 (11)0.0496 (6)
H30B0.10230.90140.78440.060*
C31B0.2493 (2)1.0051 (2)1.00396 (13)0.0656 (7)
H31C0.19531.02991.04070.079*
H31D0.27841.06740.97510.079*
C32B0.3500 (2)0.9261 (2)1.02815 (12)0.0603 (7)
C33B0.4081 (2)0.8409 (3)0.99891 (14)0.0771 (9)
H33B0.38470.83060.96290.093*
C34B0.5005 (3)0.7704 (3)1.02169 (15)0.0859 (10)
H34B0.53830.71321.00120.103*
C35B0.5362 (3)0.7842 (3)1.07383 (17)0.0929 (10)
H35B0.59890.73731.08900.111*
C36B0.4795 (4)0.8671 (3)1.10359 (19)0.1157 (14)
H36B0.50330.87671.13960.139*
C37B0.3866 (3)0.9377 (3)1.08115 (16)0.0958 (11)
H37B0.34850.99391.10250.115*
C38B0.2602 (3)0.5761 (2)0.88731 (15)0.0809 (9)
C39B0.1573 (4)0.5278 (2)0.8917 (2)0.1152 (13)
H39D0.17490.45100.90620.173*
H39E0.13650.54320.84970.173*
H39F0.09350.55770.92200.173*
Cl1B0.40960 (6)1.13171 (6)0.69486 (4)0.0808 (2)
N1B0.18697 (16)0.95909 (16)0.96957 (9)0.0524 (5)
N2B0.25708 (18)0.68690 (15)0.85980 (10)0.0577 (5)
O1B0.19531 (14)1.08500 (13)0.87397 (8)0.0559 (4)
O2B0.00075 (12)0.97815 (12)0.86691 (7)0.0481 (4)
O3B0.07547 (16)0.73540 (14)0.82998 (10)0.0713 (5)
O4B0.3451 (3)0.52419 (18)0.90667 (14)0.1253 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0467 (13)0.0397 (12)0.0541 (15)0.0020 (10)0.0109 (11)0.0130 (11)
C2A0.0650 (17)0.0614 (16)0.0551 (16)0.0001 (14)0.0182 (13)0.0128 (13)
C3A0.081 (2)0.0690 (18)0.0521 (16)0.0034 (16)0.0037 (15)0.0101 (14)
C4A0.0603 (17)0.0564 (16)0.0671 (19)0.0079 (13)0.0077 (14)0.0080 (14)
C5A0.0462 (14)0.0462 (14)0.0675 (17)0.0047 (11)0.0033 (12)0.0162 (12)
C6A0.0398 (12)0.0395 (12)0.0535 (14)0.0011 (10)0.0094 (10)0.0129 (10)
C7A0.0353 (11)0.0396 (12)0.0518 (13)0.0009 (9)0.0139 (10)0.0097 (10)
C8A0.0394 (12)0.0348 (12)0.0582 (15)0.0011 (10)0.0144 (11)0.0112 (11)
C9A0.0406 (12)0.0411 (12)0.0617 (15)0.0081 (10)0.0165 (11)0.0058 (11)
C10A0.0391 (12)0.0444 (13)0.0546 (14)0.0068 (10)0.0175 (10)0.0072 (10)
C11A0.0380 (11)0.0381 (12)0.0484 (13)0.0042 (9)0.0129 (10)0.0096 (10)
C12A0.0388 (12)0.0520 (14)0.0452 (13)0.0004 (10)0.0137 (10)0.0172 (11)
C13A0.0424 (13)0.0681 (16)0.0533 (14)0.0076 (12)0.0130 (11)0.0198 (12)
C14A0.0380 (13)0.094 (2)0.0611 (16)0.0057 (14)0.0091 (12)0.0362 (16)
C15A0.0429 (15)0.085 (2)0.082 (2)0.0168 (14)0.0241 (14)0.0426 (17)
C16A0.0553 (16)0.0605 (16)0.0798 (19)0.0101 (13)0.0270 (14)0.0261 (14)
C17A0.0468 (13)0.0494 (14)0.0551 (14)0.0029 (11)0.0179 (11)0.0215 (11)
C18A0.0461 (13)0.0404 (12)0.0512 (14)0.0021 (10)0.0153 (11)0.0129 (10)
C19A0.0400 (13)0.0575 (15)0.0530 (15)0.0002 (11)0.0167 (11)0.0028 (12)
C20A0.0585 (16)0.0788 (19)0.0604 (17)0.0185 (15)0.0190 (13)0.0029 (14)
C21A0.0614 (18)0.099 (2)0.074 (2)0.0209 (17)0.0163 (16)0.0218 (19)
C22A0.061 (2)0.129 (3)0.060 (2)0.004 (2)0.0037 (16)0.011 (2)
C23A0.074 (2)0.113 (3)0.064 (2)0.010 (2)0.0126 (17)0.0192 (19)
C24A0.0569 (16)0.0734 (18)0.0623 (18)0.0050 (14)0.0160 (14)0.0128 (15)
C25A0.0408 (12)0.0453 (13)0.0588 (15)0.0032 (10)0.0157 (11)0.0075 (11)
C26A0.0503 (14)0.0451 (14)0.0703 (17)0.0049 (11)0.0201 (12)0.0039 (12)
C27A0.0582 (16)0.0526 (15)0.0785 (19)0.0059 (13)0.0318 (14)0.0053 (13)
C28A0.0409 (13)0.0699 (17)0.0696 (17)0.0021 (13)0.0234 (12)0.0188 (14)
C29A0.0466 (15)0.0720 (18)0.086 (2)0.0162 (13)0.0235 (14)0.0011 (15)
C30A0.0523 (15)0.0573 (16)0.0827 (19)0.0110 (13)0.0283 (14)0.0084 (14)
C31A0.0619 (16)0.0532 (15)0.0779 (18)0.0051 (12)0.0305 (14)0.0251 (13)
C32A0.0506 (14)0.0502 (14)0.0623 (16)0.0127 (11)0.0217 (12)0.0126 (12)
C33A0.0743 (19)0.087 (2)0.075 (2)0.0096 (16)0.0323 (16)0.0324 (17)
C34A0.074 (2)0.101 (3)0.105 (3)0.0177 (19)0.0313 (19)0.040 (2)
C35A0.0605 (19)0.083 (2)0.104 (3)0.0077 (17)0.0363 (18)0.003 (2)
C36A0.072 (2)0.085 (2)0.0712 (19)0.0309 (17)0.0362 (16)0.0075 (17)
C37A0.0648 (17)0.0677 (17)0.0636 (17)0.0212 (14)0.0213 (14)0.0117 (13)
C38A0.0729 (19)0.0475 (15)0.0646 (17)0.0028 (14)0.0182 (14)0.0058 (13)
C39A0.083 (2)0.0544 (17)0.100 (2)0.0212 (15)0.0249 (18)0.0074 (16)
Cl1A0.0526 (4)0.1110 (7)0.1330 (8)0.0034 (4)0.0485 (5)0.0215 (6)
N1A0.0483 (11)0.0447 (11)0.0598 (12)0.0067 (9)0.0216 (10)0.0124 (9)
N2A0.0498 (11)0.0375 (10)0.0604 (12)0.0004 (9)0.0182 (9)0.0105 (9)
O1A0.0602 (10)0.0464 (9)0.0659 (11)0.0184 (8)0.0178 (9)0.0034 (8)
O2A0.0393 (8)0.0470 (9)0.0587 (10)0.0021 (7)0.0160 (7)0.0133 (8)
O3A0.0470 (10)0.0472 (9)0.0858 (13)0.0115 (8)0.0256 (9)0.0047 (9)
O4A0.0870 (15)0.0665 (13)0.1068 (17)0.0060 (11)0.0314 (13)0.0155 (12)
C1B0.0414 (13)0.0575 (15)0.0530 (15)0.0058 (11)0.0018 (11)0.0094 (12)
C2B0.0623 (18)0.082 (2)0.0549 (17)0.0053 (16)0.0009 (14)0.0061 (15)
C3B0.079 (2)0.088 (2)0.068 (2)0.0018 (19)0.0082 (18)0.0137 (18)
C4B0.073 (2)0.083 (2)0.098 (3)0.0274 (18)0.009 (2)0.015 (2)
C5B0.0572 (17)0.0668 (18)0.083 (2)0.0174 (14)0.0025 (14)0.0031 (15)
C6B0.0364 (12)0.0504 (14)0.0586 (15)0.0030 (10)0.0001 (11)0.0063 (12)
C8B0.0340 (12)0.0482 (14)0.0527 (14)0.0001 (10)0.0052 (10)0.0122 (11)
C7B0.0313 (11)0.0460 (13)0.0534 (14)0.0030 (9)0.0088 (10)0.0066 (10)
C9B0.0347 (11)0.0431 (12)0.0600 (15)0.0067 (10)0.0109 (10)0.0069 (11)
C10B0.0326 (11)0.0432 (12)0.0541 (14)0.0062 (9)0.0124 (10)0.0075 (10)
C11B0.0343 (11)0.0432 (12)0.0535 (14)0.0045 (10)0.0085 (10)0.0081 (10)
C12B0.0367 (12)0.0541 (14)0.0456 (13)0.0007 (11)0.0082 (10)0.0132 (11)
C13B0.0380 (13)0.0734 (17)0.0565 (15)0.0093 (12)0.0079 (11)0.0151 (13)
C14B0.0381 (14)0.111 (3)0.0617 (17)0.0110 (15)0.0081 (12)0.0250 (17)
C15B0.0386 (15)0.123 (3)0.0653 (18)0.0147 (17)0.0143 (13)0.0280 (19)
C16B0.0593 (17)0.083 (2)0.0607 (17)0.0262 (16)0.0164 (14)0.0227 (15)
C17B0.0493 (14)0.0601 (16)0.0468 (14)0.0074 (12)0.0112 (11)0.0164 (12)
C18B0.0534 (15)0.0455 (14)0.0568 (15)0.0086 (12)0.0096 (12)0.0105 (11)
C19B0.0310 (11)0.0537 (14)0.0566 (15)0.0003 (10)0.0136 (10)0.0020 (12)
C20B0.0480 (14)0.0642 (17)0.0723 (18)0.0168 (13)0.0158 (13)0.0075 (14)
C21B0.0567 (18)0.087 (2)0.089 (2)0.0215 (16)0.0164 (17)0.0225 (19)
C22B0.0575 (19)0.113 (3)0.075 (2)0.0058 (19)0.0032 (17)0.032 (2)
C23B0.068 (2)0.113 (3)0.0580 (19)0.013 (2)0.0049 (16)0.0043 (19)
C24B0.0451 (14)0.0723 (18)0.0640 (18)0.0039 (13)0.0122 (13)0.0096 (14)
C25B0.0320 (11)0.0451 (13)0.0507 (13)0.0064 (10)0.0061 (10)0.0057 (10)
C26B0.0461 (13)0.0445 (13)0.0631 (16)0.0083 (11)0.0108 (11)0.0039 (11)
C27B0.0521 (15)0.0465 (14)0.0681 (17)0.0000 (12)0.0198 (13)0.0037 (12)
C28B0.0389 (12)0.0608 (15)0.0526 (14)0.0015 (11)0.0159 (11)0.0078 (12)
C29B0.0387 (12)0.0527 (14)0.0623 (15)0.0084 (11)0.0095 (11)0.0132 (12)
C30B0.0373 (12)0.0443 (13)0.0633 (15)0.0016 (10)0.0125 (11)0.0049 (11)
C31B0.0646 (17)0.0757 (18)0.0629 (17)0.0010 (14)0.0204 (14)0.0281 (14)
C32B0.0542 (15)0.0765 (18)0.0508 (15)0.0074 (13)0.0111 (12)0.0159 (13)
C33B0.0612 (17)0.109 (2)0.0623 (18)0.0100 (17)0.0193 (14)0.0342 (17)
C34B0.0664 (19)0.107 (3)0.077 (2)0.0147 (18)0.0153 (16)0.0298 (19)
C35B0.080 (2)0.113 (3)0.082 (2)0.007 (2)0.0353 (19)0.012 (2)
C36B0.135 (3)0.129 (3)0.103 (3)0.020 (3)0.080 (3)0.041 (3)
C37B0.109 (3)0.107 (3)0.084 (2)0.015 (2)0.050 (2)0.044 (2)
C38B0.111 (3)0.0450 (16)0.079 (2)0.0057 (18)0.0242 (19)0.0091 (15)
C39B0.149 (4)0.0457 (18)0.149 (4)0.028 (2)0.036 (3)0.004 (2)
Cl1B0.0626 (4)0.0850 (5)0.1025 (6)0.0078 (4)0.0497 (4)0.0183 (4)
N1B0.0488 (11)0.0582 (12)0.0500 (12)0.0047 (10)0.0114 (9)0.0126 (10)
N2B0.0654 (14)0.0411 (11)0.0625 (13)0.0052 (10)0.0158 (11)0.0115 (10)
O1B0.0543 (10)0.0505 (10)0.0645 (11)0.0118 (8)0.0152 (8)0.0080 (9)
O2B0.0320 (8)0.0540 (9)0.0550 (10)0.0021 (7)0.0088 (7)0.0088 (8)
O3B0.0699 (12)0.0534 (11)0.0984 (15)0.0225 (9)0.0290 (11)0.0065 (10)
O4B0.139 (2)0.0637 (14)0.156 (2)0.0175 (15)0.059 (2)0.0095 (15)
Geometric parameters (Å, º) top
C1A—C2A1.372 (3)C1B—C2B1.378 (4)
C1A—C6A1.383 (3)C1B—C6B1.386 (3)
C1A—N1A1.416 (3)C1B—N1B1.406 (3)
C2A—C3A1.378 (4)C2B—C3B1.370 (4)
C2A—H2A0.9300C2B—H2B0.9300
C3A—C4A1.375 (4)C3B—C4B1.364 (5)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.386 (4)C4B—C5B1.389 (4)
C4A—H4A0.9300C4B—H4B0.9300
C5A—C6A1.380 (3)C5B—C6B1.376 (3)
C5A—H5A0.9300C5B—H5B0.9300
C6A—C7A1.506 (3)C6B—C7B1.498 (3)
C7A—O2A1.407 (2)C8B—O1B1.216 (3)
C7A—C8A1.557 (3)C8B—N1B1.363 (3)
C7A—C11A1.592 (3)C8B—C7B1.551 (3)
C8A—O1A1.210 (3)C7B—O2B1.409 (2)
C8A—N1A1.364 (3)C7B—C11B1.602 (3)
C9A—O2A1.437 (3)C9B—O2B1.435 (3)
C9A—C25A1.509 (3)C9B—C25B1.503 (3)
C9A—C10A1.553 (3)C9B—C10B1.540 (3)
C9A—H9A0.9800C9B—H9B0.9800
C10A—C19A1.511 (3)C10B—C19B1.513 (3)
C10A—C11A1.574 (3)C10B—C11B1.569 (3)
C10A—H10A0.9800C10B—H10B0.9800
C11A—C12A1.514 (3)C11B—C12B1.510 (3)
C11A—C18A1.537 (3)C11B—C18B1.533 (3)
C12A—C13A1.383 (3)C12B—C13B1.375 (3)
C12A—C17A1.391 (3)C12B—C17B1.392 (3)
C13A—C14A1.385 (3)C13B—C14B1.384 (3)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.369 (4)C14B—C15B1.369 (4)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.380 (4)C15B—C16B1.375 (4)
C15A—H15A0.9300C15B—H15B0.9300
C16A—C17A1.382 (3)C16B—C17B1.390 (3)
C16A—H16A0.9300C16B—H16B0.9300
C17A—N2A1.428 (3)C17B—N2B1.427 (3)
C18A—O3A1.204 (3)C18B—O3B1.206 (3)
C18A—N2A1.396 (3)C18B—N2B1.402 (3)
C19A—C24A1.381 (4)C19B—C24B1.381 (3)
C19A—C20A1.387 (4)C19B—C20B1.388 (3)
C20A—C21A1.382 (4)C20B—C21B1.373 (4)
C20A—H20A0.9300C20B—H20B0.9300
C21A—C22A1.374 (5)C21B—C22B1.368 (5)
C21A—H21A0.9300C21B—H21B0.9300
C22A—C23A1.364 (5)C22B—C23B1.375 (5)
C22A—H22A0.9300C22B—H22B0.9300
C23A—C24A1.386 (4)C23B—C24B1.390 (4)
C23A—H23A0.9300C23B—H23B0.9300
C24A—H24A0.9300C24B—H24B0.9300
C25A—C26A1.375 (3)C25B—C26B1.376 (3)
C25A—C30A1.385 (3)C25B—C30B1.391 (3)
C26A—C27A1.382 (3)C26B—C27B1.385 (3)
C26A—H26A0.9300C26B—H26B0.9300
C27A—C28A1.367 (4)C27B—C28B1.366 (3)
C27A—H27A0.9300C27B—H27B0.9300
C28A—C29A1.367 (4)C28B—C29B1.377 (3)
C28A—Cl1A1.738 (2)C28B—Cl1B1.741 (2)
C29A—C30A1.375 (3)C29B—C30B1.376 (3)
C29A—H29A0.9300C29B—H29B0.9300
C30A—H30A0.9300C30B—H30B0.9300
C31A—N1A1.458 (3)C31B—N1B1.456 (3)
C31A—C32A1.508 (3)C31B—C32B1.511 (4)
C31A—H31A0.9700C31B—H31C0.9700
C31A—H31B0.9700C31B—H31D0.9700
C32A—C33A1.366 (4)C32B—C37B1.365 (4)
C32A—C37A1.378 (3)C32B—C33B1.374 (4)
C33A—C34A1.372 (4)C33B—C34B1.380 (4)
C33A—H33A0.9300C33B—H33B0.9300
C34A—C35A1.367 (4)C34B—C35B1.353 (4)
C34A—H34A0.9300C34B—H34B0.9300
C35A—C36A1.360 (4)C35B—C36B1.353 (5)
C35A—H35A0.9300C35B—H35B0.9300
C36A—C37A1.375 (4)C36B—C37B1.382 (4)
C36A—H36A0.9300C36B—H36B0.9300
C37A—H37A0.9300C37B—H37B0.9300
C38A—O4A1.203 (3)C38B—O4B1.196 (4)
C38A—N2A1.412 (3)C38B—N2B1.410 (3)
C38A—C39A1.492 (4)C38B—C39B1.473 (5)
C39A—H39A0.9600C39B—H39D0.9600
C39A—H39B0.9600C39B—H39E0.9600
C39A—H39C0.9600C39B—H39F0.9600
C2A—C1A—C6A122.5 (2)C2B—C1B—C6B122.2 (3)
C2A—C1A—N1A127.4 (2)C2B—C1B—N1B127.8 (3)
C6A—C1A—N1A110.0 (2)C6B—C1B—N1B109.9 (2)
C1A—C2A—C3A117.2 (3)C3B—C2B—C1B116.9 (3)
C1A—C2A—H2A121.4C3B—C2B—H2B121.5
C3A—C2A—H2A121.4C1B—C2B—H2B121.5
C4A—C3A—C2A121.7 (3)C4B—C3B—C2B122.0 (3)
C4A—C3A—H3A119.1C4B—C3B—H3B119.0
C2A—C3A—H3A119.1C2B—C3B—H3B119.0
C3A—C4A—C5A120.3 (3)C3B—C4B—C5B120.9 (3)
C3A—C4A—H4A119.9C3B—C4B—H4B119.6
C5A—C4A—H4A119.9C5B—C4B—H4B119.6
C6A—C5A—C4A118.8 (2)C6B—C5B—C4B118.1 (3)
C6A—C5A—H5A120.6C6B—C5B—H5B120.9
C4A—C5A—H5A120.6C4B—C5B—H5B120.9
C5A—C6A—C1A119.4 (2)C5B—C6B—C1B119.7 (2)
C5A—C6A—C7A131.4 (2)C5B—C6B—C7B131.1 (2)
C1A—C6A—C7A108.99 (19)C1B—C6B—C7B109.1 (2)
O2A—C7A—C6A110.20 (17)O1B—C8B—N1B126.2 (2)
O2A—C7A—C8A112.65 (17)O1B—C8B—C7B126.1 (2)
C6A—C7A—C8A101.65 (17)N1B—C8B—C7B107.7 (2)
O2A—C7A—C11A104.67 (16)O2B—C7B—C6B110.33 (17)
C6A—C7A—C11A117.65 (17)O2B—C7B—C8B112.77 (17)
C8A—C7A—C11A110.29 (17)C6B—C7B—C8B101.62 (19)
O1A—C8A—N1A126.4 (2)O2B—C7B—C11B104.57 (17)
O1A—C8A—C7A125.9 (2)C6B—C7B—C11B118.19 (18)
N1A—C8A—C7A107.66 (19)C8B—C7B—C11B109.63 (17)
O2A—C9A—C25A106.33 (18)O2B—C9B—C25B107.40 (17)
O2A—C9A—C10A105.92 (17)O2B—C9B—C10B104.99 (17)
C25A—C9A—C10A115.45 (18)C25B—C9B—C10B115.38 (19)
O2A—C9A—H9A109.6O2B—C9B—H9B109.6
C25A—C9A—H9A109.6C25B—C9B—H9B109.6
C10A—C9A—H9A109.6C10B—C9B—H9B109.6
C19A—C10A—C9A114.50 (19)C19B—C10B—C9B113.86 (18)
C19A—C10A—C11A119.29 (17)C19B—C10B—C11B120.18 (17)
C9A—C10A—C11A104.63 (17)C9B—C10B—C11B104.63 (18)
C19A—C10A—H10A105.8C19B—C10B—H10B105.7
C9A—C10A—H10A105.8C9B—C10B—H10B105.7
C11A—C10A—H10A105.8C11B—C10B—H10B105.7
C12A—C11A—C18A101.36 (17)C12B—C11B—C18B101.40 (18)
C12A—C11A—C10A123.25 (18)C12B—C11B—C10B123.37 (18)
C18A—C11A—C10A108.93 (17)C18B—C11B—C10B108.78 (18)
C12A—C11A—C7A113.36 (16)C12B—C11B—C7B113.20 (18)
C18A—C11A—C7A105.98 (17)C18B—C11B—C7B106.75 (17)
C10A—C11A—C7A102.92 (16)C10B—C11B—C7B102.47 (16)
C13A—C12A—C17A119.4 (2)C13B—C12B—C17B118.8 (2)
C13A—C12A—C11A131.6 (2)C13B—C12B—C11B131.5 (2)
C17A—C12A—C11A108.97 (19)C17B—C12B—C11B109.6 (2)
C12A—C13A—C14A118.8 (2)C12B—C13B—C14B119.4 (3)
C12A—C13A—H13A120.6C12B—C13B—H13B120.3
C14A—C13A—H13A120.6C14B—C13B—H13B120.3
C15A—C14A—C13A120.8 (3)C15B—C14B—C13B121.0 (3)
C15A—C14A—H14A119.6C15B—C14B—H14B119.5
C13A—C14A—H14A119.6C13B—C14B—H14B119.5
C14A—C15A—C16A121.7 (2)C14B—C15B—C16B121.2 (3)
C14A—C15A—H15A119.1C14B—C15B—H15B119.4
C16A—C15A—H15A119.1C16B—C15B—H15B119.4
C15A—C16A—C17A117.1 (3)C15B—C16B—C17B117.4 (3)
C15A—C16A—H16A121.4C15B—C16B—H16B121.3
C17A—C16A—H16A121.4C17B—C16B—H16B121.3
C16A—C17A—C12A122.1 (2)C16B—C17B—C12B122.1 (3)
C16A—C17A—N2A127.6 (2)C16B—C17B—N2B128.1 (2)
C12A—C17A—N2A110.08 (19)C12B—C17B—N2B109.7 (2)
O3A—C18A—N2A126.0 (2)O3B—C18B—N2B126.2 (2)
O3A—C18A—C11A125.6 (2)O3B—C18B—C11B125.2 (2)
N2A—C18A—C11A108.41 (18)N2B—C18B—C11B108.6 (2)
C24A—C19A—C20A117.7 (2)C24B—C19B—C20B118.2 (2)
C24A—C19A—C10A119.0 (2)C24B—C19B—C10B119.1 (2)
C20A—C19A—C10A123.3 (2)C20B—C19B—C10B122.5 (2)
C21A—C20A—C19A121.0 (3)C21B—C20B—C19B121.0 (3)
C21A—C20A—H20A119.5C21B—C20B—H20B119.5
C19A—C20A—H20A119.5C19B—C20B—H20B119.5
C22A—C21A—C20A120.0 (3)C22B—C21B—C20B120.3 (3)
C22A—C21A—H21A120.0C22B—C21B—H21B119.9
C20A—C21A—H21A120.0C20B—C21B—H21B119.9
C23A—C22A—C21A120.0 (3)C21B—C22B—C23B120.0 (3)
C23A—C22A—H22A120.0C21B—C22B—H22B120.0
C21A—C22A—H22A120.0C23B—C22B—H22B120.0
C22A—C23A—C24A119.9 (3)C22B—C23B—C24B119.8 (3)
C22A—C23A—H23A120.0C22B—C23B—H23B120.1
C24A—C23A—H23A120.0C24B—C23B—H23B120.1
C19A—C24A—C23A121.4 (3)C19B—C24B—C23B120.7 (3)
C19A—C24A—H24A119.3C19B—C24B—H24B119.7
C23A—C24A—H24A119.3C23B—C24B—H24B119.7
C26A—C25A—C30A118.1 (2)C26B—C25B—C30B118.4 (2)
C26A—C25A—C9A122.4 (2)C26B—C25B—C9B121.3 (2)
C30A—C25A—C9A119.5 (2)C30B—C25B—C9B120.35 (19)
C25A—C26A—C27A121.4 (2)C25B—C26B—C27B121.4 (2)
C25A—C26A—H26A119.3C25B—C26B—H26B119.3
C27A—C26A—H26A119.3C27B—C26B—H26B119.3
C28A—C27A—C26A119.1 (2)C28B—C27B—C26B118.9 (2)
C28A—C27A—H27A120.4C28B—C27B—H27B120.6
C26A—C27A—H27A120.4C26B—C27B—H27B120.6
C27A—C28A—C29A120.9 (2)C27B—C28B—C29B121.3 (2)
C27A—C28A—Cl1A120.7 (2)C27B—C28B—Cl1B120.08 (18)
C29A—C28A—Cl1A118.4 (2)C29B—C28B—Cl1B118.65 (19)
C28A—C29A—C30A119.5 (3)C30B—C29B—C28B119.3 (2)
C28A—C29A—H29A120.2C30B—C29B—H29B120.4
C30A—C29A—H29A120.2C28B—C29B—H29B120.4
C29A—C30A—C25A121.0 (2)C29B—C30B—C25B120.8 (2)
C29A—C30A—H30A119.5C29B—C30B—H30B119.6
C25A—C30A—H30A119.5C25B—C30B—H30B119.6
N1A—C31A—C32A114.10 (19)N1B—C31B—C32B113.2 (2)
N1A—C31A—H31A108.7N1B—C31B—H31C108.9
C32A—C31A—H31A108.7C32B—C31B—H31C108.9
N1A—C31A—H31B108.7N1B—C31B—H31D108.9
C32A—C31A—H31B108.7C32B—C31B—H31D108.9
H31A—C31A—H31B107.6H31C—C31B—H31D107.8
C33A—C32A—C37A118.5 (2)C37B—C32B—C33B117.3 (3)
C33A—C32A—C31A121.3 (2)C37B—C32B—C31B120.1 (3)
C37A—C32A—C31A120.2 (2)C33B—C32B—C31B122.6 (2)
C32A—C33A—C34A120.6 (3)C32B—C33B—C34B121.5 (3)
C32A—C33A—H33A119.7C32B—C33B—H33B119.3
C34A—C33A—H33A119.7C34B—C33B—H33B119.3
C35A—C34A—C33A120.7 (3)C35B—C34B—C33B120.2 (3)
C35A—C34A—H34A119.7C35B—C34B—H34B119.9
C33A—C34A—H34A119.7C33B—C34B—H34B119.9
C36A—C35A—C34A119.1 (3)C36B—C35B—C34B119.2 (3)
C36A—C35A—H35A120.5C36B—C35B—H35B120.4
C34A—C35A—H35A120.5C34B—C35B—H35B120.4
C35A—C36A—C37A120.6 (3)C35B—C36B—C37B120.9 (3)
C35A—C36A—H36A119.7C35B—C36B—H36B119.6
C37A—C36A—H36A119.7C37B—C36B—H36B119.6
C36A—C37A—C32A120.5 (3)C32B—C37B—C36B121.0 (3)
C36A—C37A—H37A119.7C32B—C37B—H37B119.5
C32A—C37A—H37A119.7C36B—C37B—H37B119.5
O4A—C38A—N2A119.2 (3)O4B—C38B—N2B119.7 (3)
O4A—C38A—C39A122.9 (3)O4B—C38B—C39B121.8 (3)
N2A—C38A—C39A117.9 (2)N2B—C38B—C39B118.5 (3)
C38A—C39A—H39A109.5C38B—C39B—H39D109.5
C38A—C39A—H39B109.5C38B—C39B—H39E109.5
H39A—C39A—H39B109.5H39D—C39B—H39E109.5
C38A—C39A—H39C109.5C38B—C39B—H39F109.5
H39A—C39A—H39C109.5H39D—C39B—H39F109.5
H39B—C39A—H39C109.5H39E—C39B—H39F109.5
C8A—N1A—C1A110.79 (18)C8B—N1B—C1B110.8 (2)
C8A—N1A—C31A124.2 (2)C8B—N1B—C31B124.8 (2)
C1A—N1A—C31A123.5 (2)C1B—N1B—C31B124.1 (2)
C18A—N2A—C38A125.8 (2)C18B—N2B—C38B126.1 (2)
C18A—N2A—C17A108.95 (18)C18B—N2B—C17B109.00 (19)
C38A—N2A—C17A125.2 (2)C38B—N2B—C17B124.8 (2)
C7A—O2A—C9A109.86 (16)C7B—O2B—C9B108.24 (15)
C6A—C1A—C2A—C3A2.3 (4)C6B—C1B—C2B—C3B1.5 (4)
N1A—C1A—C2A—C3A173.7 (2)N1B—C1B—C2B—C3B175.2 (2)
C1A—C2A—C3A—C4A1.3 (4)C1B—C2B—C3B—C4B1.6 (5)
C2A—C3A—C4A—C5A3.0 (4)C2B—C3B—C4B—C5B2.4 (5)
C3A—C4A—C5A—C6A1.2 (4)C3B—C4B—C5B—C6B0.1 (5)
C4A—C5A—C6A—C1A2.2 (3)C4B—C5B—C6B—C1B2.9 (4)
C4A—C5A—C6A—C7A176.5 (2)C4B—C5B—C6B—C7B177.8 (3)
C2A—C1A—C6A—C5A4.1 (3)C2B—C1B—C6B—C5B3.8 (4)
N1A—C1A—C6A—C5A172.52 (19)N1B—C1B—C6B—C5B173.4 (2)
C2A—C1A—C6A—C7A179.6 (2)C2B—C1B—C6B—C7B179.8 (2)
N1A—C1A—C6A—C7A3.0 (2)N1B—C1B—C6B—C7B2.5 (3)
C5A—C6A—C7A—O2A47.7 (3)C5B—C6B—C7B—O2B48.2 (3)
C1A—C6A—C7A—O2A127.10 (18)C1B—C6B—C7B—O2B127.1 (2)
C5A—C6A—C7A—C8A167.3 (2)C5B—C6B—C7B—C8B168.0 (2)
C1A—C6A—C7A—C8A7.4 (2)C1B—C6B—C7B—C8B7.3 (2)
C5A—C6A—C7A—C11A72.2 (3)C5B—C6B—C7B—C11B72.0 (3)
C1A—C6A—C7A—C11A113.1 (2)C1B—C6B—C7B—C11B112.7 (2)
O2A—C7A—C8A—O1A51.9 (3)O1B—C8B—C7B—O2B52.8 (3)
C6A—C7A—C8A—O1A169.8 (2)N1B—C8B—C7B—O2B127.95 (19)
C11A—C7A—C8A—O1A64.7 (3)O1B—C8B—C7B—C6B170.9 (2)
O2A—C7A—C8A—N1A127.49 (19)N1B—C8B—C7B—C6B9.9 (2)
C6A—C7A—C8A—N1A9.6 (2)O1B—C8B—C7B—C11B63.3 (3)
C11A—C7A—C8A—N1A115.97 (19)N1B—C8B—C7B—C11B115.99 (19)
O2A—C9A—C10A—C19A146.77 (18)O2B—C9B—C10B—C19B156.53 (17)
C25A—C9A—C10A—C19A95.9 (2)C25B—C9B—C10B—C19B85.5 (2)
O2A—C9A—C10A—C11A14.3 (2)O2B—C9B—C10B—C11B23.4 (2)
C25A—C9A—C10A—C11A131.70 (19)C25B—C9B—C10B—C11B141.41 (18)
C19A—C10A—C11A—C12A5.8 (3)C19B—C10B—C11B—C12B2.1 (3)
C9A—C10A—C11A—C12A135.4 (2)C9B—C10B—C11B—C12B127.4 (2)
C19A—C10A—C11A—C18A124.1 (2)C19B—C10B—C11B—C18B116.2 (2)
C9A—C10A—C11A—C18A106.30 (19)C9B—C10B—C11B—C18B114.32 (19)
C19A—C10A—C11A—C7A123.8 (2)C19B—C10B—C11B—C7B131.0 (2)
C9A—C10A—C11A—C7A5.9 (2)C9B—C10B—C11B—C7B1.6 (2)
O2A—C7A—C11A—C12A160.03 (17)O2B—C7B—C11B—C12B156.15 (17)
C6A—C7A—C11A—C12A77.3 (2)C6B—C7B—C11B—C12B80.7 (2)
C8A—C7A—C11A—C12A38.6 (2)C8B—C7B—C11B—C12B35.0 (2)
O2A—C7A—C11A—C18A89.68 (18)O2B—C7B—C11B—C18B93.15 (19)
C6A—C7A—C11A—C18A33.0 (2)C6B—C7B—C11B—C18B30.0 (3)
C8A—C7A—C11A—C18A148.91 (17)C8B—C7B—C11B—C18B145.70 (19)
O2A—C7A—C11A—C10A24.6 (2)O2B—C7B—C11B—C10B21.1 (2)
C6A—C7A—C11A—C10A147.34 (18)C6B—C7B—C11B—C10B144.23 (19)
C8A—C7A—C11A—C10A96.76 (19)C8B—C7B—C11B—C10B100.05 (19)
C18A—C11A—C12A—C13A169.1 (2)C18B—C11B—C12B—C13B171.6 (2)
C10A—C11A—C12A—C13A47.3 (3)C10B—C11B—C12B—C13B49.9 (4)
C7A—C11A—C12A—C13A77.8 (3)C7B—C11B—C12B—C13B74.4 (3)
C18A—C11A—C12A—C17A12.7 (2)C18B—C11B—C12B—C17B10.7 (2)
C10A—C11A—C12A—C17A134.5 (2)C10B—C11B—C12B—C17B132.5 (2)
C7A—C11A—C12A—C17A100.4 (2)C7B—C11B—C12B—C17B103.2 (2)
C17A—C12A—C13A—C14A1.2 (3)C17B—C12B—C13B—C14B0.7 (3)
C11A—C12A—C13A—C14A179.3 (2)C11B—C12B—C13B—C14B176.8 (2)
C12A—C13A—C14A—C15A1.7 (4)C12B—C13B—C14B—C15B0.7 (4)
C13A—C14A—C15A—C16A0.7 (4)C13B—C14B—C15B—C16B0.5 (4)
C14A—C15A—C16A—C17A0.8 (4)C14B—C15B—C16B—C17B0.3 (4)
C15A—C16A—C17A—C12A1.3 (4)C15B—C16B—C17B—C12B0.4 (4)
C15A—C16A—C17A—N2A173.3 (2)C15B—C16B—C17B—N2B177.0 (2)
C13A—C12A—C17A—C16A0.3 (3)C13B—C12B—C17B—C16B0.6 (4)
C11A—C12A—C17A—C16A178.2 (2)C11B—C12B—C17B—C16B177.4 (2)
C13A—C12A—C17A—N2A175.16 (19)C13B—C12B—C17B—N2B177.2 (2)
C11A—C12A—C17A—N2A6.4 (2)C11B—C12B—C17B—N2B4.8 (3)
C12A—C11A—C18A—O3A164.8 (2)C12B—C11B—C18B—O3B166.3 (2)
C10A—C11A—C18A—O3A33.5 (3)C10B—C11B—C18B—O3B34.9 (3)
C7A—C11A—C18A—O3A76.6 (3)C7B—C11B—C18B—O3B75.0 (3)
C12A—C11A—C18A—N2A14.9 (2)C12B—C11B—C18B—N2B13.1 (2)
C10A—C11A—C18A—N2A146.24 (18)C10B—C11B—C18B—N2B144.50 (18)
C7A—C11A—C18A—N2A103.63 (19)C7B—C11B—C18B—N2B105.6 (2)
C9A—C10A—C19A—C24A129.2 (2)C9B—C10B—C19B—C24B128.9 (2)
C11A—C10A—C19A—C24A105.8 (2)C11B—C10B—C19B—C24B105.9 (2)
C9A—C10A—C19A—C20A48.8 (3)C9B—C10B—C19B—C20B45.9 (3)
C11A—C10A—C19A—C20A76.2 (3)C11B—C10B—C19B—C20B79.3 (3)
C24A—C19A—C20A—C21A1.1 (4)C24B—C19B—C20B—C21B0.4 (4)
C10A—C19A—C20A—C21A179.0 (2)C10B—C19B—C20B—C21B175.2 (2)
C19A—C20A—C21A—C22A0.9 (4)C19B—C20B—C21B—C22B1.5 (4)
C20A—C21A—C22A—C23A0.1 (5)C20B—C21B—C22B—C23B1.4 (5)
C21A—C22A—C23A—C24A0.5 (5)C21B—C22B—C23B—C24B0.1 (5)
C20A—C19A—C24A—C23A0.4 (4)C20B—C19B—C24B—C23B0.9 (3)
C10A—C19A—C24A—C23A178.5 (2)C10B—C19B—C24B—C23B174.1 (2)
C22A—C23A—C24A—C19A0.4 (4)C22B—C23B—C24B—C19B1.1 (4)
O2A—C9A—C25A—C26A126.8 (2)O2B—C9B—C25B—C26B116.1 (2)
C10A—C9A—C25A—C26A116.1 (3)C10B—C9B—C25B—C26B127.2 (2)
O2A—C9A—C25A—C30A51.2 (3)O2B—C9B—C25B—C30B61.6 (3)
C10A—C9A—C25A—C30A65.9 (3)C10B—C9B—C25B—C30B55.0 (3)
C30A—C25A—C26A—C27A0.4 (4)C30B—C25B—C26B—C27B0.2 (4)
C9A—C25A—C26A—C27A178.5 (2)C9B—C25B—C26B—C27B178.0 (2)
C25A—C26A—C27A—C28A0.6 (4)C25B—C26B—C27B—C28B0.7 (4)
C26A—C27A—C28A—C29A0.3 (4)C26B—C27B—C28B—C29B1.4 (4)
C26A—C27A—C28A—Cl1A179.4 (2)C26B—C27B—C28B—Cl1B177.89 (19)
C27A—C28A—C29A—C30A0.2 (4)C27B—C28B—C29B—C30B1.4 (4)
Cl1A—C28A—C29A—C30A179.9 (2)Cl1B—C28B—C29B—C30B177.82 (18)
C28A—C29A—C30A—C25A0.4 (4)C28B—C29B—C30B—C25B0.9 (4)
C26A—C25A—C30A—C29A0.1 (4)C26B—C25B—C30B—C29B0.2 (3)
C9A—C25A—C30A—C29A178.0 (2)C9B—C25B—C30B—C29B178.1 (2)
N1A—C31A—C32A—C33A49.5 (4)N1B—C31B—C32B—C37B153.4 (3)
N1A—C31A—C32A—C37A133.2 (2)N1B—C31B—C32B—C33B26.5 (4)
C37A—C32A—C33A—C34A0.4 (4)C37B—C32B—C33B—C34B0.6 (5)
C31A—C32A—C33A—C34A176.9 (3)C31B—C32B—C33B—C34B179.5 (3)
C32A—C33A—C34A—C35A0.2 (5)C32B—C33B—C34B—C35B0.2 (5)
C33A—C34A—C35A—C36A0.2 (5)C33B—C34B—C35B—C36B0.7 (6)
C34A—C35A—C36A—C37A0.3 (5)C34B—C35B—C36B—C37B0.4 (6)
C35A—C36A—C37A—C32A0.1 (4)C33B—C32B—C37B—C36B0.9 (5)
C33A—C32A—C37A—C36A0.3 (4)C31B—C32B—C37B—C36B179.2 (3)
C31A—C32A—C37A—C36A177.1 (2)C35B—C36B—C37B—C32B0.4 (6)
O1A—C8A—N1A—C1A170.9 (2)O1B—C8B—N1B—C1B171.6 (2)
C7A—C8A—N1A—C1A8.5 (2)C7B—C8B—N1B—C1B9.1 (2)
O1A—C8A—N1A—C31A4.2 (4)O1B—C8B—N1B—C31B2.0 (4)
C7A—C8A—N1A—C31A175.14 (19)C7B—C8B—N1B—C31B177.3 (2)
C2A—C1A—N1A—C8A172.7 (2)C2B—C1B—N1B—C8B172.7 (2)
C6A—C1A—N1A—C8A3.7 (2)C6B—C1B—N1B—C8B4.4 (3)
C2A—C1A—N1A—C31A5.9 (3)C2B—C1B—N1B—C31B1.0 (4)
C6A—C1A—N1A—C31A170.5 (2)C6B—C1B—N1B—C31B178.1 (2)
C32A—C31A—N1A—C8A124.1 (2)C32B—C31B—N1B—C8B125.2 (2)
C32A—C31A—N1A—C1A70.9 (3)C32B—C31B—N1B—C1B62.0 (3)
O3A—C18A—N2A—C38A13.6 (4)O3B—C18B—N2B—C38B15.3 (4)
C11A—C18A—N2A—C38A166.6 (2)C11B—C18B—N2B—C38B165.3 (2)
O3A—C18A—N2A—C17A167.7 (2)O3B—C18B—N2B—C17B168.3 (2)
C11A—C18A—N2A—C17A12.0 (2)C11B—C18B—N2B—C17B11.1 (3)
O4A—C38A—N2A—C18A171.2 (2)O4B—C38B—N2B—C18B175.4 (3)
C39A—C38A—N2A—C18A10.0 (4)C39B—C38B—N2B—C18B4.2 (4)
O4A—C38A—N2A—C17A7.3 (4)O4B—C38B—N2B—C17B0.5 (5)
C39A—C38A—N2A—C17A171.6 (2)C39B—C38B—N2B—C17B179.9 (3)
C16A—C17A—N2A—C18A171.4 (2)C16B—C17B—N2B—C18B173.6 (2)
C12A—C17A—N2A—C18A3.7 (3)C12B—C17B—N2B—C18B4.1 (3)
C16A—C17A—N2A—C38A9.9 (4)C16B—C17B—N2B—C38B9.9 (4)
C12A—C17A—N2A—C38A175.0 (2)C12B—C17B—N2B—C38B172.4 (2)
C6A—C7A—O2A—C9A163.65 (17)C6B—C7B—O2B—C9B166.23 (18)
C8A—C7A—O2A—C9A83.6 (2)C8B—C7B—O2B—C9B80.9 (2)
C11A—C7A—O2A—C9A36.2 (2)C11B—C7B—O2B—C9B38.1 (2)
C25A—C9A—O2A—C7A155.90 (17)C25B—C9B—O2B—C7B162.90 (17)
C10A—C9A—O2A—C7A32.6 (2)C10B—C9B—O2B—C7B39.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5A—H5A···O3A0.932.573.157 (3)122
C5B—H5B···O3B0.932.563.118 (4)119
C9A—H9A···O1A0.982.693.152 (3)109
C9B—H9B···O1B0.982.533.088 (3)116
C10A—H10A···O3A0.982.392.881 (3)111
C10B—H10B···O3B0.982.342.871 (3)113
C13A—H13A···O1A0.932.643.157 (3)115
C13B—H13B···O1B0.932.493.003 (3)115
C16A—H16A···O4A0.932.302.840 (4)117
C16B—H16B···O4B0.932.292.835 (5)117
C20A—H20A···O1A0.932.433.256 (3)148
C20B—H20B···O1B0.932.703.515 (3)147
C27B—H27B···O1Ai0.932.593.374 (3)142
C30A—H30A···O3A0.932.473.314 (3)151
C30B—H30B···O3B0.932.853.701 (3)153
C31A—H31A···O1A0.972.532.913 (3)104
C31B—H31D···O1B0.972.552.921 (3)104
C15A—H15A···Cg3(C19B–C24B)0.932.913.808 (14)163
C33A—H33A···Cg4(C12A–C17A)0.932.893.717 (3)149
C33B—H33B···Cg5(C12B–C17B)0.932.643.485 (3)151
Symmetry code: (i) x1, y+1, z.
(III) 1''-Acetyl-1-benzyl-4',5'-diphenyl-4',5'-dihydrodispiro[indoline-3,2'-furan-3',3''-indoline]-2,2''-dione top
Crystal data top
C39H30N2O4F(000) = 1240
Mr = 590.65Dx = 1.286 Mg m3
Triclinic, P1Melting point: 456 K
a = 9.7565 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 16.6868 (16) ÅCell parameters from 5092 reflections
c = 19.9593 (19) Åθ = 2.4–21.3°
α = 71.653 (2)°µ = 0.08 mm1
β = 81.657 (2)°T = 294 K
γ = 89.314 (2)°Needle, colorless
V = 3049.7 (5) Å30.11 × 0.08 × 0.06 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
6882 reflections with I > 2σ(I)
ω scansRint = 0.036
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
θmax = 25.0°, θmin = 1.4°
Tmin = 0.96, Tmax = 0.99h = 1111
29800 measured reflectionsk = 1919
10763 independent reflectionsl = 2323
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.070H-atom parameters constrained
wR(F2) = 0.149 w = 1/[σ2(Fo2) + (0.0505P)2 + 0.8037P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
10763 reflectionsΔρmax = 0.22 e Å3
813 parametersΔρmin = 0.17 e Å3
Crystal data top
C39H30N2O4γ = 89.314 (2)°
Mr = 590.65V = 3049.7 (5) Å3
Triclinic, P1Z = 4
a = 9.7565 (10) ÅMo Kα radiation
b = 16.6868 (16) ŵ = 0.08 mm1
c = 19.9593 (19) ÅT = 294 K
α = 71.653 (2)°0.11 × 0.08 × 0.06 mm
β = 81.657 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
10763 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
6882 reflections with I > 2σ(I)
Tmin = 0.96, Tmax = 0.99Rint = 0.036
29800 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0700 restraints
wR(F2) = 0.149H-atom parameters constrained
S = 1.09Δρmax = 0.22 e Å3
10763 reflectionsΔρmin = 0.17 e Å3
813 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1A0.9292 (3)0.66340 (16)0.69310 (14)0.0573 (7)
C2A1.0358 (4)0.66726 (19)0.63901 (16)0.0743 (9)
H2A1.01920.66100.59620.089*
C3A1.1680 (4)0.6808 (2)0.65046 (19)0.0818 (11)
H3A1.24190.68400.61450.098*
C4A1.1935 (3)0.6896 (2)0.71335 (19)0.0767 (10)
H4A1.28410.69770.71990.092*
C5A1.0845 (3)0.68656 (18)0.76760 (16)0.0655 (8)
H5A1.10140.69200.81070.079*
C6A0.9517 (3)0.67536 (16)0.75628 (14)0.0509 (7)
C7A0.8153 (3)0.66699 (16)0.80431 (13)0.0485 (7)
C8A0.7161 (3)0.63756 (17)0.76209 (14)0.0542 (7)
C9A0.7062 (3)0.61634 (16)0.92145 (13)0.0479 (6)
H9A0.62420.58640.91660.057*
C10A0.6811 (2)0.71203 (15)0.90047 (13)0.0448 (6)
H10A0.73330.73390.92980.054*
C11A0.7580 (2)0.74921 (15)0.82183 (13)0.0454 (6)
C12A0.6900 (3)0.80860 (16)0.76294 (13)0.0505 (7)
C13A0.5626 (3)0.80414 (19)0.74198 (15)0.0619 (8)
H13A0.50110.75890.76680.074*
C14A0.5265 (4)0.8669 (2)0.68415 (17)0.0789 (10)
H14A0.43990.86410.67050.095*
C15A0.6162 (5)0.9325 (2)0.64708 (18)0.0874 (11)
H15A0.59060.97370.60780.105*
C16A0.7447 (4)0.9396 (2)0.66623 (17)0.0800 (10)
H16A0.80590.98470.64060.096*
C17A0.7796 (3)0.87694 (17)0.72516 (15)0.0602 (8)
C18A0.8842 (3)0.80232 (17)0.82162 (16)0.0546 (7)
C19A0.5318 (3)0.73458 (16)0.91701 (13)0.0471 (6)
C20A0.4203 (3)0.6902 (2)0.90795 (15)0.0654 (8)
H20A0.43670.64630.88880.078*
C21A0.2860 (3)0.7099 (3)0.92674 (18)0.0841 (10)
H21A0.21290.67920.92030.101*
C22A0.2593 (4)0.7738 (3)0.9546 (2)0.0932 (12)
H22A0.16830.78720.96700.112*
C23A0.3672 (4)0.8184 (2)0.96447 (19)0.0870 (11)
H23A0.34930.86230.98350.104*
C24A0.5030 (3)0.79864 (18)0.94625 (15)0.0622 (8)
H24A0.57550.82890.95380.075*
C25A0.7417 (3)0.57877 (16)0.99551 (13)0.0496 (7)
C26A0.6404 (3)0.54221 (18)1.05194 (15)0.0655 (8)
H26A0.54920.53931.04410.079*
C27A0.6726 (5)0.5095 (2)1.12059 (17)0.0824 (11)
H27A0.60260.48571.15860.099*
C28A0.8047 (5)0.5119 (2)1.13261 (19)0.0899 (11)
H28A0.82600.48971.17870.108*
C29A0.9057 (4)0.5469 (3)1.0774 (2)0.1079 (14)
H29A0.99700.54811.08540.130*
C30A0.8743 (3)0.5807 (2)1.00904 (17)0.0891 (11)
H30A0.94490.60520.97160.107*
C31A0.7281 (4)0.6229 (2)0.64126 (16)0.0827 (10)
H31A0.63000.60930.65730.099*
H31B0.77160.57290.63450.099*
C32A0.7457 (3)0.6925 (2)0.57063 (15)0.0659 (8)
C33A0.7514 (3)0.7765 (2)0.56645 (17)0.0729 (9)
H33A0.74540.79120.60800.087*
C34A0.7660 (3)0.8388 (2)0.50110 (19)0.0811 (10)
H34A0.76980.89520.49900.097*
C35A0.7748 (3)0.8187 (3)0.43915 (19)0.0877 (11)
H35A0.78470.86110.39520.105*
C36A0.7687 (3)0.7357 (3)0.44279 (18)0.0852 (11)
H36A0.77410.72150.40100.102*
C37A0.7548 (3)0.6729 (2)0.50763 (18)0.0752 (9)
H37A0.75140.61660.50930.090*
C38A1.0177 (4)0.9267 (3)0.7323 (3)0.1062 (14)
C39A1.1367 (4)0.9099 (3)0.7717 (3)0.153 (2)
H39A1.11680.92720.81350.230*
H39B1.21720.94090.74170.230*
H39C1.15390.85050.78550.230*
N1A0.7870 (3)0.64435 (14)0.69650 (12)0.0621 (6)
N2A0.9007 (3)0.87137 (14)0.75878 (13)0.0664 (7)
O1A0.5965 (2)0.61316 (13)0.78326 (10)0.0718 (6)
O2A0.82178 (18)0.60682 (10)0.87153 (9)0.0533 (5)
O3A0.9568 (2)0.78663 (13)0.86773 (12)0.0708 (6)
O4A1.0189 (4)0.9846 (2)0.6787 (2)0.1670 (15)
C1B0.3966 (3)0.66787 (18)0.19443 (15)0.0611 (8)
C2B0.3740 (4)0.6507 (2)0.13385 (17)0.0855 (11)
H2B0.44010.66560.09300.103*
C3B0.2513 (4)0.6109 (3)0.13551 (19)0.1064 (14)
H3B0.23410.59820.09530.128*
C4B0.1526 (4)0.5894 (3)0.1956 (2)0.1095 (14)
H4B0.07090.56100.19600.131*
C5B0.1743 (3)0.6098 (2)0.25536 (17)0.0845 (11)
H5B0.10700.59620.29570.101*
C6B0.2955 (3)0.65014 (18)0.25435 (14)0.0587 (8)
C7B0.3512 (3)0.67667 (17)0.31074 (13)0.0525 (7)
C8B0.5065 (3)0.69567 (17)0.27855 (16)0.0558 (7)
C9B0.3493 (3)0.64670 (16)0.43178 (13)0.0517 (7)
H9B0.44560.66540.42850.062*
C10B0.2580 (3)0.72289 (16)0.41355 (13)0.0485 (7)
H10B0.16240.69990.42670.058*
C11B0.2836 (3)0.75674 (16)0.32999 (13)0.0471 (6)
C12B0.3621 (3)0.83932 (16)0.29240 (13)0.0487 (7)
C13B0.4889 (3)0.86791 (18)0.30007 (15)0.0598 (8)
H13B0.53880.83460.33430.072*
C14B0.5409 (4)0.9463 (2)0.25652 (19)0.0748 (9)
H14B0.62660.96600.26130.090*
C15B0.4675 (4)0.9952 (2)0.20653 (19)0.0818 (11)
H15B0.50521.04750.17710.098*
C16B0.3397 (4)0.9695 (2)0.19824 (16)0.0746 (9)
H16B0.28981.00380.16440.090*
C17B0.2877 (3)0.89059 (18)0.24230 (14)0.0564 (7)
C18B0.1444 (3)0.77372 (19)0.30262 (15)0.0582 (7)
C19B0.2660 (3)0.78642 (16)0.45256 (12)0.0476 (7)
C20B0.3841 (3)0.80219 (18)0.47761 (14)0.0576 (7)
H20B0.46480.77480.46840.069*
C21B0.3842 (4)0.8580 (2)0.51612 (16)0.0697 (9)
H21B0.46490.86800.53240.084*
C22B0.2665 (4)0.8985 (2)0.53035 (17)0.0766 (9)
H22B0.26660.93570.55660.092*
C23B0.1492 (4)0.8841 (2)0.50592 (18)0.0769 (9)
H23B0.06900.91190.51520.092*
C24B0.1486 (3)0.82850 (19)0.46735 (15)0.0637 (8)
H24B0.06760.81920.45100.076*
C25B0.3041 (3)0.58141 (17)0.50313 (14)0.0550 (7)
C26B0.3909 (3)0.5596 (2)0.55366 (17)0.0732 (9)
H26B0.47910.58490.54360.088*
C27B0.3486 (4)0.5001 (2)0.61952 (19)0.0912 (11)
H27B0.40800.48640.65360.109*
C28B0.2208 (5)0.4616 (2)0.63468 (19)0.0912 (11)
H28B0.19300.42120.67880.109*
C29B0.1340 (4)0.4823 (2)0.58510 (19)0.0875 (11)
H29B0.04660.45590.59520.105*
C30B0.1749 (3)0.54203 (19)0.51983 (15)0.0712 (9)
H30B0.11410.55610.48640.085*
C31B0.6528 (3)0.70634 (19)0.16345 (17)0.0747 (9)
H31C0.65760.66280.14050.090*
H31D0.72490.69630.19360.090*
C32B0.6829 (3)0.79056 (19)0.10680 (14)0.0586 (8)
C33B0.6056 (4)0.8591 (2)0.10648 (16)0.0795 (10)
H33B0.52790.85350.14090.095*
C34B0.6406 (5)0.9364 (2)0.05598 (19)0.1055 (14)
H34B0.58650.98250.05670.127*
C35B0.7536 (5)0.9463 (3)0.0051 (2)0.1127 (15)
H35B0.77750.99890.02860.135*
C36B0.8309 (4)0.8786 (3)0.00398 (19)0.1021 (13)
H36B0.90770.88470.03100.123*
C37B0.7965 (3)0.8007 (2)0.05428 (17)0.0797 (10)
H37B0.85020.75470.05290.096*
C38B0.0523 (4)0.8859 (3)0.2049 (2)0.0951 (12)
C39B0.0759 (4)0.8353 (3)0.2140 (2)0.1394 (19)
H39D0.12590.82650.26100.209*
H39E0.05280.78170.20790.209*
H39F0.13250.86480.17910.209*
N1B0.5191 (2)0.69772 (14)0.20844 (12)0.0609 (6)
N2B0.1565 (2)0.85061 (16)0.24650 (12)0.0625 (6)
O1B0.6002 (2)0.70484 (13)0.30892 (11)0.0701 (6)
O2B0.33736 (19)0.61006 (11)0.37630 (9)0.0595 (5)
O3B0.0413 (2)0.72933 (15)0.32619 (11)0.0780 (6)
O4B0.0744 (3)0.9560 (2)0.16236 (17)0.1432 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.075 (2)0.0444 (16)0.0443 (17)0.0066 (14)0.0055 (15)0.0084 (13)
C2A0.092 (3)0.069 (2)0.0536 (19)0.0109 (19)0.0090 (18)0.0172 (16)
C3A0.086 (3)0.076 (2)0.059 (2)0.0177 (19)0.0250 (19)0.0039 (18)
C4A0.062 (2)0.077 (2)0.072 (2)0.0071 (17)0.0107 (18)0.0061 (18)
C5A0.064 (2)0.065 (2)0.0571 (19)0.0076 (16)0.0002 (16)0.0088 (15)
C6A0.0553 (18)0.0451 (16)0.0443 (16)0.0033 (13)0.0038 (13)0.0079 (13)
C7A0.0552 (16)0.0458 (16)0.0383 (15)0.0008 (13)0.0007 (12)0.0072 (12)
C8A0.0650 (19)0.0464 (17)0.0478 (17)0.0049 (14)0.0014 (15)0.0132 (13)
C9A0.0474 (15)0.0495 (16)0.0430 (15)0.0061 (12)0.0015 (12)0.0125 (13)
C10A0.0448 (15)0.0489 (16)0.0395 (14)0.0064 (12)0.0035 (11)0.0133 (12)
C11A0.0459 (15)0.0453 (15)0.0421 (15)0.0034 (12)0.0007 (12)0.0127 (12)
C12A0.0595 (18)0.0485 (16)0.0390 (15)0.0042 (14)0.0026 (13)0.0121 (13)
C13A0.068 (2)0.071 (2)0.0462 (17)0.0087 (16)0.0085 (15)0.0178 (16)
C14A0.094 (3)0.091 (3)0.051 (2)0.031 (2)0.0164 (19)0.0208 (19)
C15A0.126 (3)0.078 (3)0.053 (2)0.040 (3)0.013 (2)0.0144 (19)
C16A0.121 (3)0.051 (2)0.051 (2)0.006 (2)0.016 (2)0.0048 (16)
C17A0.076 (2)0.0481 (18)0.0493 (17)0.0037 (15)0.0090 (16)0.0138 (15)
C18A0.0502 (17)0.0527 (18)0.0604 (19)0.0051 (14)0.0034 (15)0.0220 (16)
C19A0.0501 (16)0.0518 (16)0.0350 (14)0.0022 (13)0.0026 (12)0.0090 (13)
C20A0.0540 (19)0.082 (2)0.0605 (19)0.0038 (16)0.0058 (15)0.0250 (17)
C21A0.050 (2)0.121 (3)0.077 (2)0.005 (2)0.0080 (17)0.025 (2)
C22A0.058 (2)0.116 (3)0.092 (3)0.021 (2)0.004 (2)0.021 (2)
C23A0.089 (3)0.077 (2)0.088 (3)0.021 (2)0.009 (2)0.027 (2)
C24A0.065 (2)0.0602 (19)0.0569 (18)0.0019 (15)0.0019 (15)0.0178 (15)
C25A0.0560 (17)0.0437 (15)0.0442 (16)0.0009 (13)0.0009 (13)0.0107 (13)
C26A0.084 (2)0.0594 (19)0.0487 (18)0.0217 (16)0.0037 (16)0.0167 (15)
C27A0.134 (3)0.058 (2)0.045 (2)0.032 (2)0.015 (2)0.0134 (16)
C28A0.139 (4)0.068 (2)0.057 (2)0.019 (2)0.024 (3)0.0087 (18)
C29A0.089 (3)0.161 (4)0.067 (3)0.033 (3)0.029 (2)0.021 (3)
C30A0.064 (2)0.133 (3)0.055 (2)0.007 (2)0.0074 (17)0.009 (2)
C31A0.120 (3)0.073 (2)0.064 (2)0.013 (2)0.0082 (19)0.0354 (19)
C32A0.071 (2)0.080 (2)0.0531 (19)0.0031 (17)0.0042 (15)0.0322 (17)
C33A0.084 (2)0.083 (2)0.057 (2)0.0093 (19)0.0078 (17)0.0304 (19)
C34A0.078 (2)0.088 (3)0.072 (2)0.0153 (19)0.0113 (19)0.019 (2)
C35A0.068 (2)0.126 (4)0.060 (2)0.009 (2)0.0130 (17)0.014 (2)
C36A0.066 (2)0.144 (4)0.052 (2)0.001 (2)0.0084 (16)0.039 (2)
C37A0.069 (2)0.103 (3)0.067 (2)0.0035 (18)0.0069 (17)0.046 (2)
C38A0.094 (3)0.073 (3)0.127 (4)0.038 (2)0.024 (3)0.013 (3)
C39A0.073 (3)0.123 (4)0.234 (6)0.056 (3)0.002 (3)0.020 (4)
N1A0.0794 (18)0.0598 (16)0.0482 (14)0.0066 (13)0.0000 (13)0.0228 (12)
N2A0.0694 (17)0.0474 (15)0.0700 (17)0.0157 (12)0.0150 (14)0.0119 (13)
O1A0.0723 (14)0.0779 (15)0.0660 (13)0.0204 (12)0.0014 (11)0.0272 (11)
O2A0.0609 (11)0.0477 (11)0.0436 (10)0.0033 (9)0.0017 (9)0.0079 (9)
O3A0.0532 (12)0.0824 (15)0.0804 (15)0.0144 (11)0.0094 (11)0.0303 (12)
O4A0.157 (3)0.120 (3)0.158 (3)0.072 (2)0.015 (2)0.035 (2)
C1B0.074 (2)0.0552 (18)0.0505 (18)0.0120 (15)0.0078 (15)0.0183 (14)
C2B0.105 (3)0.094 (3)0.055 (2)0.024 (2)0.0153 (19)0.0313 (19)
C3B0.127 (3)0.139 (4)0.063 (2)0.041 (3)0.001 (2)0.052 (2)
C4B0.114 (3)0.146 (4)0.077 (3)0.060 (3)0.001 (2)0.052 (3)
C5B0.087 (2)0.107 (3)0.059 (2)0.044 (2)0.0105 (17)0.0322 (19)
C6B0.0668 (19)0.0604 (18)0.0451 (16)0.0179 (15)0.0060 (14)0.0170 (14)
C7B0.0590 (17)0.0506 (16)0.0416 (15)0.0122 (13)0.0053 (13)0.0109 (13)
C8B0.0609 (19)0.0415 (16)0.060 (2)0.0051 (14)0.0005 (16)0.0122 (14)
C9B0.0593 (17)0.0487 (16)0.0445 (16)0.0060 (13)0.0009 (13)0.0135 (13)
C10B0.0471 (15)0.0536 (17)0.0386 (14)0.0078 (13)0.0003 (12)0.0085 (13)
C11B0.0453 (15)0.0530 (16)0.0394 (14)0.0086 (12)0.0007 (12)0.0115 (12)
C12B0.0540 (17)0.0509 (16)0.0377 (15)0.0038 (13)0.0046 (13)0.0139 (13)
C13B0.0600 (19)0.0610 (19)0.0575 (18)0.0105 (15)0.0063 (14)0.0235 (15)
C14B0.080 (2)0.063 (2)0.079 (2)0.0249 (18)0.0153 (19)0.0297 (19)
C15B0.111 (3)0.050 (2)0.072 (2)0.017 (2)0.026 (2)0.0175 (18)
C16B0.101 (3)0.062 (2)0.0511 (19)0.0087 (19)0.0057 (18)0.0121 (16)
C17B0.0667 (19)0.0594 (19)0.0396 (16)0.0005 (15)0.0045 (14)0.0163 (14)
C18B0.0563 (19)0.073 (2)0.0447 (17)0.0074 (16)0.0002 (14)0.0202 (15)
C19B0.0513 (17)0.0504 (16)0.0333 (14)0.0008 (13)0.0003 (12)0.0051 (12)
C20B0.0581 (18)0.0666 (19)0.0519 (17)0.0027 (15)0.0077 (14)0.0242 (15)
C21B0.079 (2)0.075 (2)0.060 (2)0.0017 (18)0.0178 (17)0.0246 (17)
C22B0.110 (3)0.062 (2)0.061 (2)0.005 (2)0.012 (2)0.0249 (17)
C23B0.083 (2)0.069 (2)0.077 (2)0.0231 (18)0.0006 (19)0.0263 (19)
C24B0.0599 (19)0.069 (2)0.0582 (18)0.0064 (16)0.0058 (15)0.0157 (16)
C25B0.0678 (19)0.0471 (17)0.0463 (16)0.0002 (14)0.0012 (15)0.0125 (13)
C26B0.070 (2)0.068 (2)0.069 (2)0.0083 (17)0.0100 (18)0.0045 (18)
C27B0.097 (3)0.086 (3)0.067 (2)0.018 (2)0.017 (2)0.009 (2)
C28B0.116 (3)0.069 (2)0.060 (2)0.010 (2)0.010 (2)0.0097 (18)
C29B0.100 (3)0.076 (2)0.064 (2)0.021 (2)0.013 (2)0.0013 (19)
C30B0.084 (2)0.072 (2)0.0478 (18)0.0184 (18)0.0018 (16)0.0068 (16)
C31B0.071 (2)0.064 (2)0.082 (2)0.0030 (16)0.0209 (17)0.0281 (18)
C32B0.0624 (18)0.066 (2)0.0497 (17)0.0102 (16)0.0081 (14)0.0276 (15)
C33B0.104 (3)0.066 (2)0.058 (2)0.008 (2)0.0207 (18)0.0188 (18)
C34B0.161 (4)0.070 (3)0.069 (2)0.005 (2)0.021 (3)0.014 (2)
C35B0.162 (4)0.091 (3)0.065 (3)0.032 (3)0.021 (3)0.012 (2)
C36B0.102 (3)0.129 (4)0.062 (2)0.043 (3)0.030 (2)0.028 (3)
C37B0.069 (2)0.104 (3)0.065 (2)0.0132 (19)0.0149 (17)0.037 (2)
C38B0.092 (3)0.131 (4)0.053 (2)0.018 (3)0.019 (2)0.014 (2)
C39B0.094 (3)0.191 (5)0.132 (4)0.004 (3)0.070 (3)0.026 (4)
N1B0.0604 (15)0.0591 (15)0.0578 (16)0.0096 (12)0.0139 (12)0.0206 (12)
N2B0.0638 (16)0.0783 (18)0.0427 (14)0.0073 (14)0.0105 (12)0.0144 (13)
O1B0.0590 (13)0.0707 (14)0.0786 (15)0.0013 (11)0.0114 (11)0.0201 (12)
O2B0.0795 (13)0.0503 (11)0.0437 (11)0.0117 (10)0.0029 (9)0.0125 (9)
O3B0.0524 (13)0.1065 (18)0.0683 (14)0.0194 (12)0.0023 (11)0.0203 (13)
O4B0.125 (2)0.165 (3)0.099 (2)0.021 (2)0.0390 (19)0.025 (2)
Geometric parameters (Å, º) top
C1A—C2A1.372 (4)C1B—C2B1.375 (4)
C1A—C6A1.385 (4)C1B—C6B1.390 (4)
C1A—N1A1.414 (4)C1B—N1B1.398 (4)
C2A—C3A1.376 (5)C2B—C3B1.367 (5)
C2A—H2A0.9300C2B—H2B0.9300
C3A—C4A1.367 (5)C3B—C4B1.377 (5)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.392 (4)C4B—C5B1.384 (4)
C4A—H4A0.9300C4B—H4B0.9300
C5A—C6A1.372 (4)C5B—C6B1.362 (4)
C5A—H5A0.9300C5B—H5B0.9300
C6A—C7A1.504 (3)C6B—C7B1.501 (4)
C7A—O2A1.410 (3)C7B—O2B1.415 (3)
C7A—C8A1.548 (4)C7B—C8B1.552 (4)
C7A—C11A1.595 (3)C7B—C11B1.611 (4)
C8A—O1A1.211 (3)C8B—O1B1.204 (3)
C8A—N1A1.360 (3)C8B—N1B1.376 (4)
C9A—O2A1.435 (3)C9B—O2B1.442 (3)
C9A—C25A1.503 (4)C9B—C25B1.504 (4)
C9A—C10A1.544 (3)C9B—C10B1.523 (4)
C9A—H9A0.9800C9B—H9B0.9800
C10A—C19A1.516 (3)C10B—C19B1.508 (4)
C10A—C11A1.571 (3)C10B—C11B1.566 (3)
C10A—H10A0.9800C10B—H10B0.9800
C11A—C12A1.510 (4)C11B—C12B1.502 (3)
C11A—C18A1.525 (4)C11B—C18B1.528 (4)
C12A—C13A1.377 (4)C12B—C13B1.377 (4)
C12A—C17A1.388 (4)C12B—C17B1.384 (4)
C13A—C14A1.379 (4)C13B—C14B1.377 (4)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.356 (5)C14B—C15B1.362 (5)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.380 (5)C15B—C16B1.372 (5)
C15A—H15A0.9300C15B—H15B0.9300
C16A—C17A1.387 (4)C16B—C17B1.387 (4)
C16A—H16A0.9300C16B—H16B0.9300
C17A—N2A1.429 (4)C17B—N2B1.430 (3)
C18A—O3A1.204 (3)C18B—O3B1.201 (3)
C18A—N2A1.401 (4)C18B—N2B1.405 (4)
C19A—C24A1.378 (4)C19B—C20B1.379 (4)
C19A—C20A1.388 (4)C19B—C24B1.381 (4)
C20A—C21A1.374 (4)C20B—C21B1.382 (4)
C20A—H20A0.9300C20B—H20B0.9300
C21A—C22A1.356 (5)C21B—C22B1.365 (4)
C21A—H21A0.9300C21B—H21B0.9300
C22A—C23A1.368 (5)C22B—C23B1.359 (4)
C22A—H22A0.9300C22B—H22B0.9300
C23A—C24A1.387 (4)C23B—C24B1.380 (4)
C23A—H23A0.9300C23B—H23B0.9300
C24A—H24A0.9300C24B—H24B0.9300
C25A—C30A1.362 (4)C25B—C26B1.370 (4)
C25A—C26A1.370 (4)C25B—C30B1.376 (4)
C26A—C27A1.387 (4)C26B—C27B1.384 (4)
C26A—H26A0.9300C26B—H26B0.9300
C27A—C28A1.348 (5)C27B—C28B1.359 (5)
C27A—H27A0.9300C27B—H27B0.9300
C28A—C29A1.349 (5)C28B—C29B1.355 (5)
C28A—H28A0.9300C28B—H28B0.9300
C29A—C30A1.380 (4)C29B—C30B1.375 (4)
C29A—H29A0.9300C29B—H29B0.9300
C30A—H30A0.9300C30B—H30B0.9300
C31A—N1A1.453 (4)C31B—N1B1.453 (3)
C31A—C32A1.506 (4)C31B—C32B1.501 (4)
C31A—H31A0.9700C31B—H31C0.9700
C31A—H31B0.9700C31B—H31D0.9700
C32A—C33A1.379 (4)C32B—C33B1.361 (4)
C32A—C37A1.387 (4)C32B—C37B1.383 (4)
C33A—C34A1.378 (4)C33B—C34B1.375 (4)
C33A—H33A0.9300C33B—H33B0.9300
C34A—C35A1.370 (5)C34B—C35B1.359 (5)
C34A—H34A0.9300C34B—H34B0.9300
C35A—C36A1.366 (5)C35B—C36B1.355 (5)
C35A—H35A0.9300C35B—H35B0.9300
C36A—C37A1.375 (5)C36B—C37B1.378 (5)
C36A—H36A0.9300C36B—H36B0.9300
C37A—H37A0.9300C37B—H37B0.9300
C38A—O4A1.194 (5)C38B—O4B1.209 (5)
C38A—N2A1.406 (4)C38B—N2B1.412 (4)
C38A—C39A1.471 (6)C38B—C39B1.474 (5)
C39A—H39A0.9600C39B—H39D0.9600
C39A—H39B0.9600C39B—H39E0.9600
C39A—H39C0.9600C39B—H39F0.9600
C2A—C1A—C6A121.9 (3)C2B—C1B—C6B121.6 (3)
C2A—C1A—N1A128.3 (3)C2B—C1B—N1B128.0 (3)
C6A—C1A—N1A109.7 (2)C6B—C1B—N1B110.3 (3)
C1A—C2A—C3A117.5 (3)C3B—C2B—C1B117.9 (3)
C1A—C2A—H2A121.2C3B—C2B—H2B121.1
C3A—C2A—H2A121.2C1B—C2B—H2B121.1
C4A—C3A—C2A121.7 (3)C2B—C3B—C4B121.3 (3)
C4A—C3A—H3A119.2C2B—C3B—H3B119.4
C2A—C3A—H3A119.2C4B—C3B—H3B119.4
C3A—C4A—C5A120.3 (3)C3B—C4B—C5B120.4 (3)
C3A—C4A—H4A119.8C3B—C4B—H4B119.8
C5A—C4A—H4A119.8C5B—C4B—H4B119.8
C6A—C5A—C4A118.7 (3)C6B—C5B—C4B119.1 (3)
C6A—C5A—H5A120.6C6B—C5B—H5B120.5
C4A—C5A—H5A120.6C4B—C5B—H5B120.5
C5A—C6A—C1A119.7 (3)C5B—C6B—C1B119.7 (3)
C5A—C6A—C7A131.1 (3)C5B—C6B—C7B131.5 (2)
C1A—C6A—C7A109.0 (2)C1B—C6B—C7B108.7 (2)
O2A—C7A—C6A110.6 (2)O2B—C7B—C6B111.2 (2)
O2A—C7A—C8A112.2 (2)O2B—C7B—C8B110.3 (2)
C6A—C7A—C8A101.8 (2)C6B—C7B—C8B101.6 (2)
O2A—C7A—C11A104.76 (19)O2B—C7B—C11B105.34 (19)
C6A—C7A—C11A117.8 (2)C6B—C7B—C11B117.6 (2)
C8A—C7A—C11A109.9 (2)C8B—C7B—C11B110.7 (2)
O1A—C8A—N1A125.9 (3)O1B—C8B—N1B125.6 (3)
O1A—C8A—C7A126.3 (2)O1B—C8B—C7B127.1 (3)
N1A—C8A—C7A107.8 (2)N1B—C8B—C7B107.2 (2)
O2A—C9A—C25A108.3 (2)O2B—C9B—C25B108.9 (2)
O2A—C9A—C10A105.79 (18)O2B—C9B—C10B102.9 (2)
C25A—C9A—C10A114.0 (2)C25B—C9B—C10B115.1 (2)
O2A—C9A—H9A109.5O2B—C9B—H9B109.9
C25A—C9A—H9A109.5C25B—C9B—H9B109.9
C10A—C9A—H9A109.5C10B—C9B—H9B109.9
C19A—C10A—C9A114.8 (2)C19B—C10B—C9B117.8 (2)
C19A—C10A—C11A118.5 (2)C19B—C10B—C11B117.3 (2)
C9A—C10A—C11A104.73 (19)C9B—C10B—C11B103.8 (2)
C19A—C10A—H10A105.9C19B—C10B—H10B105.6
C9A—C10A—H10A105.9C9B—C10B—H10B105.6
C11A—C10A—H10A105.9C11B—C10B—H10B105.6
C12A—C11A—C18A101.7 (2)C12B—C11B—C18B102.0 (2)
C12A—C11A—C10A122.4 (2)C12B—C11B—C10B119.6 (2)
C18A—C11A—C10A108.9 (2)C18B—C11B—C10B109.2 (2)
C12A—C11A—C7A113.6 (2)C12B—C11B—C7B114.8 (2)
C18A—C11A—C7A106.7 (2)C18B—C11B—C7B109.5 (2)
C10A—C11A—C7A102.75 (19)C10B—C11B—C7B101.7 (2)
C13A—C12A—C17A118.9 (3)C13B—C12B—C17B119.5 (3)
C13A—C12A—C11A131.5 (2)C13B—C12B—C11B130.8 (3)
C17A—C12A—C11A109.6 (2)C17B—C12B—C11B109.7 (2)
C12A—C13A—C14A119.9 (3)C12B—C13B—C14B119.3 (3)
C12A—C13A—H13A120.0C12B—C13B—H13B120.3
C14A—C13A—H13A120.0C14B—C13B—H13B120.3
C15A—C14A—C13A120.4 (3)C15B—C14B—C13B120.3 (3)
C15A—C14A—H14A119.8C15B—C14B—H14B119.8
C13A—C14A—H14A119.8C13B—C14B—H14B119.8
C14A—C15A—C16A121.6 (3)C14B—C15B—C16B122.0 (3)
C14A—C15A—H15A119.2C14B—C15B—H15B119.0
C16A—C15A—H15A119.2C16B—C15B—H15B119.0
C15A—C16A—C17A117.7 (3)C15B—C16B—C17B117.4 (3)
C15A—C16A—H16A121.2C15B—C16B—H16B121.3
C17A—C16A—H16A121.2C17B—C16B—H16B121.3
C16A—C17A—C12A121.5 (3)C12B—C17B—C16B121.4 (3)
C16A—C17A—N2A129.2 (3)C12B—C17B—N2B110.0 (2)
C12A—C17A—N2A109.3 (2)C16B—C17B—N2B128.6 (3)
O3A—C18A—N2A126.5 (3)O3B—C18B—N2B125.9 (3)
O3A—C18A—C11A125.3 (3)O3B—C18B—C11B125.5 (3)
N2A—C18A—C11A108.2 (3)N2B—C18B—C11B108.6 (2)
C24A—C19A—C20A117.5 (3)C20B—C19B—C24B117.5 (3)
C24A—C19A—C10A119.4 (2)C20B—C19B—C10B123.3 (2)
C20A—C19A—C10A122.9 (2)C24B—C19B—C10B119.2 (2)
C21A—C20A—C19A121.3 (3)C19B—C20B—C21B121.0 (3)
C21A—C20A—H20A119.4C19B—C20B—H20B119.5
C19A—C20A—H20A119.4C21B—C20B—H20B119.5
C22A—C21A—C20A120.5 (3)C22B—C21B—C20B120.3 (3)
C22A—C21A—H21A119.7C22B—C21B—H21B119.8
C20A—C21A—H21A119.7C20B—C21B—H21B119.8
C21A—C22A—C23A119.5 (3)C23B—C22B—C21B119.6 (3)
C21A—C22A—H22A120.2C23B—C22B—H22B120.2
C23A—C22A—H22A120.2C21B—C22B—H22B120.2
C22A—C23A—C24A120.5 (3)C22B—C23B—C24B120.3 (3)
C22A—C23A—H23A119.8C22B—C23B—H23B119.8
C24A—C23A—H23A119.8C24B—C23B—H23B119.8
C19A—C24A—C23A120.7 (3)C23B—C24B—C19B121.2 (3)
C19A—C24A—H24A119.7C23B—C24B—H24B119.4
C23A—C24A—H24A119.7C19B—C24B—H24B119.4
C30A—C25A—C26A117.8 (3)C26B—C25B—C30B118.0 (3)
C30A—C25A—C9A121.5 (2)C26B—C25B—C9B120.7 (3)
C26A—C25A—C9A120.6 (3)C30B—C25B—C9B121.3 (3)
C25A—C26A—C27A120.6 (3)C25B—C26B—C27B120.6 (3)
C25A—C26A—H26A119.7C25B—C26B—H26B119.7
C27A—C26A—H26A119.7C27B—C26B—H26B119.7
C28A—C27A—C26A120.4 (3)C28B—C27B—C26B120.4 (3)
C28A—C27A—H27A119.8C28B—C27B—H27B119.8
C26A—C27A—H27A119.8C26B—C27B—H27B119.8
C27A—C28A—C29A119.5 (3)C29B—C28B—C27B119.6 (3)
C27A—C28A—H28A120.2C29B—C28B—H28B120.2
C29A—C28A—H28A120.2C27B—C28B—H28B120.2
C28A—C29A—C30A120.4 (4)C28B—C29B—C30B120.2 (3)
C28A—C29A—H29A119.8C28B—C29B—H29B119.9
C30A—C29A—H29A119.8C30B—C29B—H29B119.9
C25A—C30A—C29A121.1 (3)C29B—C30B—C25B121.1 (3)
C25A—C30A—H30A119.4C29B—C30B—H30B119.4
C29A—C30A—H30A119.4C25B—C30B—H30B119.4
N1A—C31A—C32A113.7 (3)N1B—C31B—C32B115.0 (3)
N1A—C31A—H31A108.8N1B—C31B—H31C108.5
C32A—C31A—H31A108.8C32B—C31B—H31C108.5
N1A—C31A—H31B108.8N1B—C31B—H31D108.5
C32A—C31A—H31B108.8C32B—C31B—H31D108.5
H31A—C31A—H31B107.7H31C—C31B—H31D107.5
C33A—C32A—C37A118.3 (3)C33B—C32B—C37B118.1 (3)
C33A—C32A—C31A121.7 (3)C33B—C32B—C31B122.5 (3)
C37A—C32A—C31A120.0 (3)C37B—C32B—C31B119.4 (3)
C34A—C33A—C32A120.4 (3)C32B—C33B—C34B120.9 (3)
C34A—C33A—H33A119.8C32B—C33B—H33B119.5
C32A—C33A—H33A119.8C34B—C33B—H33B119.5
C35A—C34A—C33A120.9 (4)C35B—C34B—C33B120.7 (4)
C35A—C34A—H34A119.6C35B—C34B—H34B119.6
C33A—C34A—H34A119.6C33B—C34B—H34B119.6
C36A—C35A—C34A119.1 (4)C36B—C35B—C34B119.2 (4)
C36A—C35A—H35A120.4C36B—C35B—H35B120.4
C34A—C35A—H35A120.4C34B—C35B—H35B120.4
C35A—C36A—C37A120.6 (3)C35B—C36B—C37B120.5 (4)
C35A—C36A—H36A119.7C35B—C36B—H36B119.7
C37A—C36A—H36A119.7C37B—C36B—H36B119.7
C36A—C37A—C32A120.7 (3)C36B—C37B—C32B120.5 (4)
C36A—C37A—H37A119.7C36B—C37B—H37B119.7
C32A—C37A—H37A119.7C32B—C37B—H37B119.7
O4A—C38A—N2A119.8 (4)O4B—C38B—N2B117.9 (4)
O4A—C38A—C39A122.0 (4)O4B—C38B—C39B123.3 (4)
N2A—C38A—C39A118.2 (4)N2B—C38B—C39B118.8 (4)
C38A—C39A—H39A109.5C38B—C39B—H39D109.5
C38A—C39A—H39B109.5C38B—C39B—H39E109.5
H39A—C39A—H39B109.5H39D—C39B—H39E109.5
C38A—C39A—H39C109.5C38B—C39B—H39F109.5
H39A—C39A—H39C109.5H39D—C39B—H39F109.5
H39B—C39A—H39C109.5H39E—C39B—H39F109.5
C8A—N1A—C1A110.9 (2)C8B—N1B—C1B110.7 (2)
C8A—N1A—C31A124.1 (3)C8B—N1B—C31B122.3 (3)
C1A—N1A—C31A124.5 (2)C1B—N1B—C31B124.8 (2)
C18A—N2A—C38A125.8 (3)C18B—N2B—C38B125.7 (3)
C18A—N2A—C17A109.3 (2)C18B—N2B—C17B108.7 (2)
C38A—N2A—C17A124.9 (3)C38B—N2B—C17B125.4 (3)
C7A—O2A—C9A109.07 (18)C7B—O2B—C9B107.58 (19)
C6A—C1A—C2A—C3A2.1 (4)C6B—C1B—C2B—C3B3.6 (5)
N1A—C1A—C2A—C3A175.1 (3)N1B—C1B—C2B—C3B171.1 (3)
C1A—C2A—C3A—C4A0.4 (5)C1B—C2B—C3B—C4B0.6 (6)
C2A—C3A—C4A—C5A1.1 (5)C2B—C3B—C4B—C5B1.8 (7)
C3A—C4A—C5A—C6A0.6 (5)C3B—C4B—C5B—C6B1.1 (6)
C4A—C5A—C6A—C1A3.1 (4)C4B—C5B—C6B—C1B1.8 (5)
C4A—C5A—C6A—C7A178.0 (3)C4B—C5B—C6B—C7B176.9 (4)
C2A—C1A—C6A—C5A3.9 (4)C2B—C1B—C6B—C5B4.3 (5)
N1A—C1A—C6A—C5A173.8 (2)N1B—C1B—C6B—C5B171.3 (3)
C2A—C1A—C6A—C7A179.9 (3)C2B—C1B—C6B—C7B179.6 (3)
N1A—C1A—C6A—C7A2.2 (3)N1B—C1B—C6B—C7B4.8 (3)
C5A—C6A—C7A—O2A49.2 (4)C5B—C6B—C7B—O2B47.8 (4)
C1A—C6A—C7A—O2A126.2 (2)C1B—C6B—C7B—O2B127.7 (2)
C5A—C6A—C7A—C8A168.6 (3)C5B—C6B—C7B—C8B165.2 (3)
C1A—C6A—C7A—C8A6.8 (3)C1B—C6B—C7B—C8B10.3 (3)
C5A—C6A—C7A—C11A71.2 (4)C5B—C6B—C7B—C11B73.7 (4)
C1A—C6A—C7A—C11A113.4 (3)C1B—C6B—C7B—C11B110.8 (3)
O2A—C7A—C8A—O1A52.8 (4)O2B—C7B—C8B—O1B47.7 (4)
C6A—C7A—C8A—O1A171.1 (3)C6B—C7B—C8B—O1B165.8 (3)
C11A—C7A—C8A—O1A63.3 (3)C11B—C7B—C8B—O1B68.5 (4)
O2A—C7A—C8A—N1A127.5 (2)O2B—C7B—C8B—N1B130.5 (2)
C6A—C7A—C8A—N1A9.2 (3)C6B—C7B—C8B—N1B12.4 (3)
C11A—C7A—C8A—N1A116.4 (2)C11B—C7B—C8B—N1B113.3 (2)
O2A—C9A—C10A—C19A150.0 (2)O2B—C9B—C10B—C19B168.83 (19)
C25A—C9A—C10A—C19A91.1 (3)C25B—C9B—C10B—C19B72.9 (3)
O2A—C9A—C10A—C11A18.2 (2)O2B—C9B—C10B—C11B37.2 (2)
C25A—C9A—C10A—C11A137.1 (2)C25B—C9B—C10B—C11B155.5 (2)
C19A—C10A—C11A—C12A2.0 (3)C19B—C10B—C11B—C12B21.6 (3)
C9A—C10A—C11A—C12A131.6 (2)C9B—C10B—C11B—C12B110.2 (3)
C19A—C10A—C11A—C18A120.1 (2)C19B—C10B—C11B—C18B95.2 (3)
C9A—C10A—C11A—C18A110.4 (2)C9B—C10B—C11B—C18B133.0 (2)
C19A—C10A—C11A—C7A127.0 (2)C19B—C10B—C11B—C7B149.2 (2)
C9A—C10A—C11A—C7A2.5 (2)C9B—C10B—C11B—C7B17.3 (2)
O2A—C7A—C11A—C12A157.1 (2)O2B—C7B—C11B—C12B139.0 (2)
C6A—C7A—C11A—C12A79.5 (3)C6B—C7B—C11B—C12B96.5 (3)
C8A—C7A—C11A—C12A36.4 (3)C8B—C7B—C11B—C12B19.7 (3)
O2A—C7A—C11A—C18A91.7 (2)O2B—C7B—C11B—C18B107.1 (2)
C6A—C7A—C11A—C18A31.7 (3)C6B—C7B—C11B—C18B17.5 (3)
C8A—C7A—C11A—C18A147.6 (2)C8B—C7B—C11B—C18B133.6 (2)
O2A—C7A—C11A—C10A22.9 (2)O2B—C7B—C11B—C10B8.3 (2)
C6A—C7A—C11A—C10A146.2 (2)C6B—C7B—C11B—C10B132.9 (2)
C8A—C7A—C11A—C10A97.9 (2)C8B—C7B—C11B—C10B110.9 (2)
C18A—C11A—C12A—C13A170.2 (3)C18B—C11B—C12B—C13B172.2 (3)
C10A—C11A—C12A—C13A48.6 (4)C10B—C11B—C12B—C13B51.8 (4)
C7A—C11A—C12A—C13A75.6 (3)C7B—C11B—C12B—C13B69.5 (3)
C18A—C11A—C12A—C17A11.3 (3)C18B—C11B—C12B—C17B8.6 (3)
C10A—C11A—C12A—C17A132.9 (2)C10B—C11B—C12B—C17B129.1 (2)
C7A—C11A—C12A—C17A102.9 (2)C7B—C11B—C12B—C17B109.7 (3)
C17A—C12A—C13A—C14A0.2 (4)C17B—C12B—C13B—C14B1.5 (4)
C11A—C12A—C13A—C14A178.2 (3)C11B—C12B—C13B—C14B177.6 (3)
C12A—C13A—C14A—C15A0.9 (5)C12B—C13B—C14B—C15B0.2 (4)
C13A—C14A—C15A—C16A1.0 (5)C13B—C14B—C15B—C16B1.1 (5)
C14A—C15A—C16A—C17A0.0 (5)C14B—C15B—C16B—C17B1.0 (5)
C15A—C16A—C17A—C12A1.2 (4)C13B—C12B—C17B—C16B1.7 (4)
C15A—C16A—C17A—N2A175.9 (3)C11B—C12B—C17B—C16B177.6 (2)
C13A—C12A—C17A—C16A1.3 (4)C13B—C12B—C17B—N2B176.5 (2)
C11A—C12A—C17A—C16A177.4 (2)C11B—C12B—C17B—N2B4.2 (3)
C13A—C12A—C17A—N2A176.3 (2)C15B—C16B—C17B—C12B0.4 (4)
C11A—C12A—C17A—N2A5.0 (3)C15B—C16B—C17B—N2B177.4 (3)
C12A—C11A—C18A—O3A166.5 (3)C12B—C11B—C18B—O3B168.6 (3)
C10A—C11A—C18A—O3A36.1 (4)C10B—C11B—C18B—O3B41.2 (4)
C7A—C11A—C18A—O3A74.2 (3)C7B—C11B—C18B—O3B69.4 (3)
C12A—C11A—C18A—N2A13.8 (3)C12B—C11B—C18B—N2B10.1 (3)
C10A—C11A—C18A—N2A144.3 (2)C10B—C11B—C18B—N2B137.6 (2)
C7A—C11A—C18A—N2A105.5 (2)C7B—C11B—C18B—N2B111.9 (2)
C9A—C10A—C19A—C24A137.1 (2)C9B—C10B—C19B—C20B29.7 (3)
C11A—C10A—C19A—C24A98.1 (3)C11B—C10B—C19B—C20B95.5 (3)
C9A—C10A—C19A—C20A39.0 (3)C9B—C10B—C19B—C24B147.1 (2)
C11A—C10A—C19A—C20A85.8 (3)C11B—C10B—C19B—C24B87.7 (3)
C24A—C19A—C20A—C21A0.6 (4)C24B—C19B—C20B—C21B0.1 (4)
C10A—C19A—C20A—C21A176.8 (3)C10B—C19B—C20B—C21B176.8 (2)
C19A—C20A—C21A—C22A0.2 (5)C19B—C20B—C21B—C22B0.2 (4)
C20A—C21A—C22A—C23A0.4 (6)C20B—C21B—C22B—C23B0.5 (5)
C21A—C22A—C23A—C24A0.1 (6)C21B—C22B—C23B—C24B0.4 (5)
C20A—C19A—C24A—C23A1.2 (4)C22B—C23B—C24B—C19B0.1 (5)
C10A—C19A—C24A—C23A177.5 (3)C20B—C19B—C24B—C23B0.2 (4)
C22A—C23A—C24A—C19A0.9 (5)C10B—C19B—C24B—C23B176.8 (3)
O2A—C9A—C25A—C30A32.3 (4)O2B—C9B—C25B—C26B123.7 (3)
C10A—C9A—C25A—C30A85.2 (3)C10B—C9B—C25B—C26B121.4 (3)
O2A—C9A—C25A—C26A148.5 (2)O2B—C9B—C25B—C30B56.5 (3)
C10A—C9A—C25A—C26A94.0 (3)C10B—C9B—C25B—C30B58.4 (4)
C30A—C25A—C26A—C27A0.9 (4)C30B—C25B—C26B—C27B0.5 (5)
C9A—C25A—C26A—C27A178.3 (3)C9B—C25B—C26B—C27B179.4 (3)
C25A—C26A—C27A—C28A1.1 (5)C25B—C26B—C27B—C28B0.9 (5)
C26A—C27A—C28A—C29A0.3 (6)C26B—C27B—C28B—C29B0.6 (6)
C27A—C28A—C29A—C30A0.7 (6)C27B—C28B—C29B—C30B0.1 (6)
C26A—C25A—C30A—C29A0.0 (5)C28B—C29B—C30B—C25B0.6 (5)
C9A—C25A—C30A—C29A179.3 (3)C26B—C25B—C30B—C29B0.3 (5)
C28A—C29A—C30A—C25A0.8 (7)C9B—C25B—C30B—C29B179.9 (3)
N1A—C31A—C32A—C33A29.9 (5)N1B—C31B—C32B—C33B13.0 (4)
N1A—C31A—C32A—C37A150.9 (3)N1B—C31B—C32B—C37B169.7 (3)
C37A—C32A—C33A—C34A0.1 (5)C37B—C32B—C33B—C34B0.9 (5)
C31A—C32A—C33A—C34A179.2 (3)C31B—C32B—C33B—C34B176.4 (3)
C32A—C33A—C34A—C35A0.1 (5)C32B—C33B—C34B—C35B0.0 (6)
C33A—C34A—C35A—C36A0.1 (5)C33B—C34B—C35B—C36B0.8 (7)
C34A—C35A—C36A—C37A0.4 (5)C34B—C35B—C36B—C37B0.7 (7)
C35A—C36A—C37A—C32A0.4 (5)C35B—C36B—C37B—C32B0.2 (6)
C33A—C32A—C37A—C36A0.2 (5)C33B—C32B—C37B—C36B1.0 (5)
C31A—C32A—C37A—C36A179.0 (3)C31B—C32B—C37B—C36B176.4 (3)
O1A—C8A—N1A—C1A171.7 (3)O1B—C8B—N1B—C1B167.8 (3)
C7A—C8A—N1A—C1A8.6 (3)C7B—C8B—N1B—C1B10.4 (3)
O1A—C8A—N1A—C31A0.1 (5)O1B—C8B—N1B—C31B4.0 (4)
C7A—C8A—N1A—C31A179.6 (2)C7B—C8B—N1B—C31B174.2 (2)
C2A—C1A—N1A—C8A173.2 (3)C2B—C1B—N1B—C8B171.4 (3)
C6A—C1A—N1A—C8A4.2 (3)C6B—C1B—N1B—C8B3.8 (3)
C2A—C1A—N1A—C31A1.5 (5)C2B—C1B—N1B—C31B8.1 (5)
C6A—C1A—N1A—C31A176.0 (3)C6B—C1B—N1B—C31B167.1 (3)
C32A—C31A—N1A—C8A127.3 (3)C32B—C31B—N1B—C8B108.1 (3)
C32A—C31A—N1A—C1A62.0 (4)C32B—C31B—N1B—C1B90.5 (3)
O3A—C18A—N2A—C38A11.6 (5)O3B—C18B—N2B—C38B4.8 (5)
C11A—C18A—N2A—C38A168.0 (3)C11B—C18B—N2B—C38B176.5 (3)
O3A—C18A—N2A—C17A168.6 (3)O3B—C18B—N2B—C17B170.5 (3)
C11A—C18A—N2A—C17A11.8 (3)C11B—C18B—N2B—C17B8.2 (3)
O4A—C38A—N2A—C18A178.5 (4)O4B—C38B—N2B—C18B173.9 (3)
C39A—C38A—N2A—C18A2.5 (6)C39B—C38B—N2B—C18B7.4 (5)
O4A—C38A—N2A—C17A1.8 (6)O4B—C38B—N2B—C17B0.6 (5)
C39A—C38A—N2A—C17A177.2 (4)C39B—C38B—N2B—C17B178.1 (3)
C16A—C17A—N2A—C18A173.0 (3)C12B—C17B—N2B—C18B2.6 (3)
C12A—C17A—N2A—C18A4.4 (3)C16B—C17B—N2B—C18B175.4 (3)
C16A—C17A—N2A—C38A7.3 (5)C12B—C17B—N2B—C38B177.9 (3)
C12A—C17A—N2A—C38A175.4 (3)C16B—C17B—N2B—C38B0.0 (5)
C6A—C7A—O2A—C9A164.6 (2)C6B—C7B—O2B—C9B161.6 (2)
C8A—C7A—O2A—C9A82.5 (2)C8B—C7B—O2B—C9B86.4 (2)
C11A—C7A—O2A—C9A36.7 (2)C11B—C7B—O2B—C9B33.1 (3)
C25A—C9A—O2A—C7A157.9 (2)C25B—C9B—O2B—C7B167.6 (2)
C10A—C9A—O2A—C7A35.4 (2)C10B—C9B—O2B—C7B45.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5A—H5A···O3A0.932.533.109 (4)121
C5B—H5B···O3B0.932.532.973 (4)109
C9A—H9A···O1A0.982.613.115 (3)112
C9B—H9B···O1B0.982.533.125 (3)119
C10A—H10A···O3A0.982.382.876 (3)111
C10B—H10B···O3B0.982.392.910 (3)113
C13A—H13A···O1A0.932.533.057 (4)116
C13B—H13B···O1B0.932.422.880 (4)110
C16A—H16A···O4A0.932.312.853 (6)116
C16B—H16B···O4B0.932.272.813 (5)117
C27A—H27A···O1Ai0.932.463.310 (4)152
C31A—H31A···O1A0.972.512.892 (4)103
C31B—H31D···O1B0.972.492.866 (4)103
C3A—H3A···Cg1(C19B–C24B)ii0.932.983.474 (4)115
C24A—H24A···Cg2(C32B–C37B)iii0.932.863.677 (3)147
C31B—H31C···Cg3(C25A–C30A)iv0.972.963.889 (4)161
C33A—H33A···Cg4(C12A–C17A)0.932.723.602 (4)158
C33B—H33B···Cg5(C12B–C17B)0.932.803.572 (4)142
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y+1, z; (iii) x, y, z+1; (iv) x, y, z1.
(IV) 1''-Acetyl-1-benzyl-4',5'-diphenyl-4',5'-dihydrodispiro[indoline-3,2'-furan-3',3''-indoline]-2,2''-dione acetonitrile hemisolvate top
Crystal data top
C39H30N2O4·0.5C2H3NF(000) = 1284
Mr = 611.18Dx = 1.287 Mg m3
Triclinic, P1Melting point: 456 K
a = 9.6940 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 18.581 (1) ÅCell parameters from 5108 reflections
c = 20.1552 (11) Åθ = 2.2–25.4°
α = 114.872 (2)°µ = 0.08 mm1
β = 98.465 (2)°T = 294 K
γ = 99.397 (2)°Plate, colorless
V = 3153.6 (3) Å30.18 × 0.08 × 0.07 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
10357 reflections with I > 2σ(I)
ω scansRint = 0.023
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
θmax = 28.4°, θmin = 2.0°
Tmin = 0.97, Tmax = 0.99h = 1212
37306 measured reflectionsk = 2424
14817 independent reflectionsl = 2626
Refinement top
Refinement on F270 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.147 w = 1/[σ2(Fo2) + (0.063P)2 + 0.6698P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
14817 reflectionsΔρmax = 0.27 e Å3
870 parametersΔρmin = 0.16 e Å3
Crystal data top
C39H30N2O4·0.5C2H3Nγ = 99.397 (2)°
Mr = 611.18V = 3153.6 (3) Å3
Triclinic, P1Z = 4
a = 9.6940 (5) ÅMo Kα radiation
b = 18.581 (1) ŵ = 0.08 mm1
c = 20.1552 (11) ÅT = 294 K
α = 114.872 (2)°0.18 × 0.08 × 0.07 mm
β = 98.465 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
14817 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
10357 reflections with I > 2σ(I)
Tmin = 0.97, Tmax = 0.99Rint = 0.023
37306 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05870 restraints
wR(F2) = 0.147H-atom parameters constrained
S = 1.01Δρmax = 0.27 e Å3
14817 reflectionsΔρmin = 0.16 e Å3
870 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1A0.9684 (2)0.65838 (11)0.32254 (10)0.0561 (4)
C2A0.9436 (3)0.64022 (14)0.38003 (12)0.0760 (6)
H2A1.01810.65250.42090.091*
C3A0.8050 (3)0.60335 (17)0.37481 (14)0.0917 (8)
H3A0.78540.59010.41270.110*
C4A0.6949 (3)0.58568 (17)0.31487 (14)0.0916 (8)
H4A0.60240.55920.31190.110*
C5A0.7200 (2)0.60684 (14)0.25858 (11)0.0713 (6)
H5A0.64470.59570.21850.086*
C6A0.85713 (19)0.64438 (11)0.26309 (9)0.0526 (4)
C7A0.91975 (18)0.67156 (10)0.21094 (9)0.0469 (4)
C8A1.08417 (19)0.68973 (10)0.24370 (10)0.0509 (4)
C9A0.90133 (18)0.64440 (10)0.08683 (9)0.0470 (4)
H9A1.00460.66330.09200.056*
C10A0.83557 (17)0.71791 (10)0.11803 (8)0.0443 (4)
H10A0.73110.69470.10330.053*
C11A0.87964 (17)0.75002 (10)0.20514 (9)0.0446 (4)
C12A0.99083 (18)0.83002 (10)0.25514 (9)0.0468 (4)
C13A1.12463 (19)0.86160 (11)0.24904 (10)0.0562 (4)
H13A1.16000.83210.20800.067*
C14A1.2057 (2)0.93768 (13)0.30461 (13)0.0704 (6)
H14A1.29520.95970.30030.084*
C15A1.1555 (3)0.98076 (13)0.36579 (13)0.0780 (6)
H15A1.21251.03130.40290.094*
C16A1.0229 (3)0.95099 (12)0.37356 (11)0.0719 (6)
H16A0.98920.98040.41530.086*
C17A0.9407 (2)0.87550 (11)0.31709 (10)0.0545 (4)
C18A0.7489 (2)0.76548 (12)0.23796 (10)0.0540 (4)
C19A0.86030 (17)0.77899 (10)0.08723 (8)0.0446 (4)
C20A0.98645 (19)0.80060 (11)0.06850 (10)0.0549 (4)
H20A1.06240.77790.07590.066*
C21A1.0017 (2)0.85567 (13)0.03879 (11)0.0664 (5)
H21A1.08840.87070.02780.080*
C22A0.8896 (3)0.88804 (13)0.02553 (13)0.0731 (6)
H22A0.89960.92460.00510.088*
C23A0.7632 (3)0.86616 (13)0.04255 (13)0.0742 (6)
H23A0.68660.88770.03330.089*
C24A0.7482 (2)0.81247 (12)0.07332 (11)0.0595 (5)
H24A0.66150.79850.08490.071*
C25A0.82953 (19)0.58155 (10)0.00694 (9)0.0503 (4)
C26A0.9095 (2)0.55844 (13)0.04589 (11)0.0683 (5)
H26A1.00810.58190.03220.082*
C27A0.8442 (3)0.50041 (15)0.11946 (12)0.0866 (7)
H27A0.89890.48570.15500.104*
C28A0.7002 (3)0.46481 (14)0.14000 (12)0.0839 (7)
H28A0.65670.42560.18940.101*
C29A0.6206 (3)0.48690 (13)0.08796 (12)0.0778 (6)
H29A0.52240.46250.10180.093*
C30A0.6841 (2)0.54524 (12)0.01472 (10)0.0652 (5)
H30A0.62820.56020.02030.078*
C31A1.2406 (2)0.69401 (12)0.35488 (12)0.0680 (5)
H31A1.30920.68820.32360.082*
H31B1.23170.64900.36780.082*
C32A1.29944 (19)0.77276 (12)0.42587 (10)0.0554 (4)
C33A1.2547 (2)0.84198 (13)0.43622 (11)0.0693 (5)
H33A1.18020.83970.40000.083*
C34A1.3190 (3)0.91521 (15)0.49984 (13)0.0864 (7)
H34A1.28800.96190.50600.104*
C35A1.4274 (3)0.91944 (17)0.55347 (13)0.0895 (7)
H35A1.47100.96910.59600.107*
C36A1.4720 (2)0.85102 (18)0.54491 (13)0.0862 (7)
H36A1.54520.85370.58200.103*
C37A1.4091 (2)0.77794 (15)0.48163 (12)0.0713 (6)
H37A1.44040.73140.47610.086*
C38A0.7195 (3)0.85912 (17)0.36535 (16)0.0970 (8)
C39A0.5626 (4)0.8226 (2)0.3428 (2)0.1603 (17)
H39A0.54470.76610.33250.240*
H39B0.52130.82630.29840.240*
H39C0.51990.85170.38290.240*
N1A1.10114 (16)0.68723 (9)0.31102 (8)0.0564 (4)
N2A0.79684 (18)0.83479 (10)0.30883 (9)0.0608 (4)
O1A1.17954 (14)0.70178 (8)0.21454 (8)0.0652 (3)
O2A0.87908 (13)0.60776 (7)0.13617 (6)0.0521 (3)
O3A0.62711 (14)0.72464 (9)0.20860 (8)0.0723 (4)
O4A0.7843 (3)0.90724 (14)0.42882 (12)0.1412 (9)
C1B0.4849 (2)0.65903 (10)0.82671 (9)0.0537 (4)
C2B0.5926 (3)0.66188 (12)0.88114 (11)0.0693 (6)
H2B0.57190.65380.92150.083*
C3B0.7314 (3)0.67709 (14)0.87397 (12)0.0759 (6)
H3B0.80600.68010.91060.091*
C4B0.7629 (2)0.68796 (13)0.81421 (12)0.0697 (6)
H4B0.85780.69670.81010.084*
C5B0.6540 (2)0.68606 (11)0.75968 (10)0.0572 (4)
H5B0.67500.69350.71910.069*
C6B0.51482 (19)0.67299 (10)0.76730 (9)0.0475 (4)
C7B0.37501 (17)0.66401 (9)0.71719 (8)0.0443 (4)
C8B0.2621 (2)0.63286 (10)0.75277 (10)0.0518 (4)
C9B0.25123 (17)0.61449 (10)0.59310 (9)0.0458 (4)
H9B0.15740.58490.59270.055*
C10B0.26023 (16)0.70760 (9)0.62721 (8)0.0419 (3)
H10B0.32370.72940.60280.050*
C11B0.34514 (16)0.74336 (9)0.71135 (8)0.0406 (3)
C12B0.29269 (18)0.79845 (10)0.77704 (9)0.0447 (4)
C13B0.1602 (2)0.79128 (11)0.79428 (10)0.0552 (4)
H13B0.08300.74730.76140.066*
C14B0.1428 (2)0.85019 (13)0.86104 (11)0.0639 (5)
H14B0.05360.84570.87280.077*
C15B0.2563 (3)0.91503 (12)0.90975 (11)0.0661 (5)
H15B0.24320.95360.95460.079*
C16B0.3895 (2)0.92413 (11)0.89358 (10)0.0619 (5)
H16B0.46610.96830.92670.074*
C17B0.40586 (19)0.86551 (10)0.82670 (9)0.0484 (4)
C18B0.49280 (17)0.79769 (10)0.72292 (9)0.0441 (4)
C19B0.11816 (18)0.72826 (10)0.61091 (9)0.0481 (4)
C20B0.0111 (2)0.68626 (13)0.61366 (11)0.0656 (5)
H20B0.01230.64440.62750.079*
C21B0.1384 (2)0.70601 (19)0.59602 (13)0.0892 (8)
H21B0.22420.67760.59850.107*
C22B0.1392 (3)0.7668 (2)0.57491 (15)0.1023 (9)
H22B0.22510.77990.56320.123*
C23B0.0129 (3)0.80844 (18)0.57104 (15)0.0936 (8)
H23B0.01320.84950.55620.112*
C24B0.1153 (2)0.78960 (13)0.58916 (11)0.0654 (5)
H24B0.20070.81850.58670.078*
C25B0.27754 (19)0.57783 (10)0.51526 (9)0.0476 (4)
C26B0.1647 (2)0.53842 (11)0.45255 (10)0.0624 (5)
H26B0.07050.53420.45810.075*
C27B0.1901 (3)0.50460 (12)0.38054 (11)0.0781 (7)
H27B0.11300.47820.33830.094*
C28B0.3270 (3)0.51026 (13)0.37210 (12)0.0784 (7)
H28B0.34390.48770.32420.094*
C29B0.4388 (3)0.54884 (17)0.43364 (13)0.0891 (7)
H29B0.53260.55240.42770.107*
C30B0.4153 (2)0.58296 (15)0.50496 (11)0.0736 (6)
H30B0.49350.60980.54660.088*
C31B0.2653 (3)0.61257 (13)0.86711 (12)0.0764 (6)
H31C0.29240.56380.86510.092*
H31D0.16160.59820.84800.092*
C32B0.3043 (2)0.67757 (12)0.94825 (11)0.0607 (5)
C33B0.3296 (2)0.75985 (13)0.96763 (11)0.0659 (5)
H33B0.32430.77670.93010.079*
C34B0.3627 (2)0.81737 (14)1.04203 (13)0.0737 (6)
H34B0.37980.87281.05450.088*
C35B0.3707 (2)0.79339 (18)1.09784 (13)0.0812 (7)
H35B0.39300.83251.14810.097*
C36B0.3458 (2)0.71209 (19)1.07974 (13)0.0801 (7)
H36B0.35070.69581.11760.096*
C37B0.3134 (2)0.65426 (15)1.00529 (12)0.0704 (6)
H37B0.29750.59900.99320.085*
C38B0.6661 (2)0.91889 (12)0.83376 (12)0.0682 (5)
C39B0.7802 (2)0.91494 (16)0.79147 (15)0.0959 (8)
H39D0.86550.95720.82350.144*
H39E0.74720.92270.74820.144*
H39F0.80150.86240.77540.144*
N1B0.33483 (18)0.63827 (9)0.81852 (8)0.0584 (4)
N2B0.52902 (15)0.86379 (8)0.79570 (8)0.0501 (3)
O1B0.13351 (15)0.60823 (8)0.72638 (8)0.0679 (4)
O2B0.36310 (12)0.60636 (7)0.64245 (6)0.0493 (3)
O3B0.56517 (13)0.78525 (8)0.67774 (7)0.0566 (3)
O4B0.68638 (19)0.96645 (11)0.89900 (9)0.1077 (6)
C400.1678 (18)0.9849 (10)0.7561 (8)0.116 (3)0.654 (19)
H40A0.15301.03530.79160.175*0.654 (19)
H40B0.14140.94300.77130.175*0.654 (19)
H40C0.10930.96880.70700.175*0.654 (19)
C410.3157 (15)0.9959 (6)0.7539 (6)0.116 (3)0.654 (19)
N30.4317 (13)1.0040 (6)0.7503 (4)0.141 (2)0.654 (19)
C4010.145 (3)0.980 (2)0.7664 (17)0.110 (3)0.346 (19)
H40D0.10460.92330.73170.165*0.346 (19)
H40E0.07711.01110.76200.165*0.346 (19)
H40F0.16710.98670.81690.165*0.346 (19)
C4110.279 (2)1.0104 (13)0.7484 (12)0.117 (3)0.346 (19)
N310.386 (2)1.0335 (11)0.7393 (8)0.137 (4)0.346 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0607 (11)0.0518 (10)0.0471 (10)0.0046 (8)0.0027 (8)0.0212 (8)
C2A0.0857 (16)0.0852 (15)0.0537 (12)0.0080 (12)0.0018 (10)0.0381 (11)
C3A0.0991 (19)0.114 (2)0.0736 (15)0.0059 (15)0.0215 (14)0.0612 (15)
C4A0.0802 (16)0.114 (2)0.0795 (16)0.0117 (14)0.0156 (13)0.0569 (15)
C5A0.0603 (12)0.0853 (15)0.0577 (12)0.0074 (10)0.0030 (9)0.0357 (11)
C6A0.0543 (10)0.0520 (10)0.0429 (9)0.0020 (8)0.0036 (8)0.0203 (8)
C7A0.0477 (9)0.0462 (9)0.0383 (8)0.0041 (7)0.0041 (7)0.0162 (7)
C8A0.0516 (10)0.0402 (9)0.0509 (10)0.0084 (7)0.0063 (8)0.0147 (7)
C9A0.0498 (9)0.0459 (9)0.0404 (8)0.0071 (7)0.0071 (7)0.0181 (7)
C10A0.0370 (8)0.0482 (9)0.0388 (8)0.0043 (7)0.0037 (6)0.0158 (7)
C11A0.0412 (8)0.0474 (9)0.0395 (8)0.0064 (7)0.0072 (7)0.0170 (7)
C12A0.0509 (10)0.0440 (9)0.0401 (8)0.0089 (7)0.0036 (7)0.0175 (7)
C13A0.0505 (10)0.0563 (10)0.0544 (10)0.0037 (8)0.0025 (8)0.0252 (9)
C14A0.0611 (12)0.0622 (12)0.0739 (14)0.0060 (10)0.0070 (10)0.0334 (11)
C15A0.0869 (16)0.0474 (11)0.0712 (14)0.0012 (11)0.0109 (12)0.0168 (10)
C16A0.0974 (17)0.0508 (11)0.0532 (11)0.0234 (11)0.0062 (11)0.0127 (9)
C17A0.0639 (11)0.0484 (10)0.0487 (10)0.0159 (8)0.0101 (8)0.0204 (8)
C18A0.0507 (11)0.0631 (11)0.0498 (10)0.0140 (9)0.0140 (8)0.0267 (9)
C19A0.0440 (9)0.0449 (9)0.0368 (8)0.0083 (7)0.0051 (7)0.0137 (7)
C20A0.0487 (10)0.0645 (11)0.0554 (10)0.0158 (8)0.0116 (8)0.0305 (9)
C21A0.0657 (12)0.0717 (13)0.0693 (13)0.0105 (10)0.0212 (10)0.0399 (11)
C22A0.0903 (16)0.0645 (13)0.0782 (14)0.0232 (11)0.0211 (12)0.0434 (11)
C23A0.0776 (15)0.0709 (13)0.0897 (15)0.0370 (11)0.0208 (12)0.0442 (12)
C24A0.0530 (11)0.0624 (11)0.0646 (12)0.0199 (9)0.0151 (9)0.0281 (10)
C25A0.0614 (11)0.0439 (9)0.0407 (9)0.0117 (8)0.0071 (8)0.0171 (7)
C26A0.0667 (12)0.0666 (12)0.0592 (12)0.0230 (10)0.0174 (10)0.0142 (10)
C27A0.104 (2)0.0803 (15)0.0563 (13)0.0365 (14)0.0276 (13)0.0058 (11)
C28A0.1039 (19)0.0660 (13)0.0478 (12)0.0199 (13)0.0012 (12)0.0015 (10)
C29A0.0784 (15)0.0697 (13)0.0549 (12)0.0039 (11)0.0053 (11)0.0152 (10)
C30A0.0664 (12)0.0649 (12)0.0471 (10)0.0012 (10)0.0064 (9)0.0185 (9)
C31A0.0588 (12)0.0605 (12)0.0766 (13)0.0127 (9)0.0063 (10)0.0317 (10)
C32A0.0470 (10)0.0632 (11)0.0565 (10)0.0053 (8)0.0023 (8)0.0341 (9)
C33A0.0689 (13)0.0668 (13)0.0592 (12)0.0145 (10)0.0071 (10)0.0250 (10)
C34A0.0962 (18)0.0700 (14)0.0696 (14)0.0160 (12)0.0005 (13)0.0187 (12)
C35A0.0848 (17)0.0905 (18)0.0590 (13)0.0051 (14)0.0063 (12)0.0197 (12)
C36A0.0627 (13)0.121 (2)0.0629 (14)0.0017 (14)0.0115 (11)0.0484 (15)
C37A0.0549 (11)0.0931 (16)0.0731 (13)0.0107 (11)0.0008 (10)0.0521 (13)
C38A0.122 (2)0.0870 (17)0.0841 (18)0.0301 (16)0.0622 (17)0.0269 (15)
C39A0.128 (3)0.166 (3)0.156 (3)0.014 (2)0.110 (3)0.029 (3)
N1A0.0511 (9)0.0547 (9)0.0553 (9)0.0057 (7)0.0024 (7)0.0254 (7)
N2A0.0694 (10)0.0628 (10)0.0520 (9)0.0225 (8)0.0255 (8)0.0223 (8)
O1A0.0515 (7)0.0690 (8)0.0718 (9)0.0144 (6)0.0201 (7)0.0277 (7)
O2A0.0638 (7)0.0436 (6)0.0391 (6)0.0050 (5)0.0043 (5)0.0156 (5)
O3A0.0446 (7)0.0958 (11)0.0691 (9)0.0094 (7)0.0154 (6)0.0332 (8)
O4A0.178 (2)0.1246 (17)0.0826 (14)0.0274 (16)0.0698 (15)0.0033 (12)
C1B0.0722 (12)0.0414 (9)0.0421 (9)0.0146 (8)0.0061 (8)0.0166 (7)
C2B0.0922 (17)0.0653 (12)0.0499 (11)0.0264 (11)0.0039 (10)0.0276 (10)
C3B0.0847 (16)0.0747 (14)0.0567 (12)0.0324 (12)0.0092 (11)0.0232 (11)
C4B0.0595 (12)0.0682 (13)0.0676 (13)0.0222 (10)0.0005 (10)0.0213 (11)
C5B0.0573 (11)0.0573 (11)0.0524 (10)0.0193 (9)0.0092 (8)0.0203 (9)
C6B0.0572 (10)0.0400 (8)0.0386 (8)0.0138 (7)0.0042 (7)0.0134 (7)
C7B0.0501 (9)0.0410 (8)0.0363 (8)0.0094 (7)0.0071 (7)0.0143 (7)
C8B0.0621 (11)0.0401 (9)0.0470 (9)0.0060 (8)0.0115 (8)0.0171 (7)
C9B0.0430 (9)0.0443 (9)0.0415 (8)0.0057 (7)0.0050 (7)0.0153 (7)
C10B0.0418 (8)0.0448 (8)0.0355 (8)0.0084 (7)0.0085 (6)0.0161 (7)
C11B0.0412 (8)0.0406 (8)0.0370 (8)0.0089 (6)0.0085 (6)0.0157 (7)
C12B0.0531 (10)0.0425 (8)0.0379 (8)0.0143 (7)0.0104 (7)0.0170 (7)
C13B0.0578 (11)0.0598 (11)0.0477 (10)0.0171 (9)0.0167 (8)0.0221 (8)
C14B0.0707 (13)0.0750 (13)0.0571 (11)0.0331 (11)0.0289 (10)0.0307 (10)
C15B0.0971 (16)0.0577 (11)0.0474 (10)0.0345 (11)0.0266 (11)0.0193 (9)
C16B0.0847 (14)0.0442 (10)0.0466 (10)0.0149 (9)0.0119 (9)0.0129 (8)
C17B0.0599 (10)0.0413 (9)0.0430 (9)0.0136 (8)0.0098 (8)0.0187 (7)
C18B0.0442 (9)0.0437 (9)0.0429 (8)0.0094 (7)0.0054 (7)0.0206 (7)
C19B0.0476 (9)0.0527 (9)0.0361 (8)0.0153 (7)0.0076 (7)0.0130 (7)
C20B0.0492 (11)0.0809 (14)0.0599 (11)0.0136 (10)0.0102 (9)0.0277 (10)
C21B0.0476 (12)0.130 (2)0.0749 (15)0.0244 (13)0.0123 (11)0.0327 (15)
C22B0.0742 (18)0.139 (3)0.0887 (18)0.0631 (18)0.0099 (14)0.0381 (18)
C23B0.096 (2)0.1034 (19)0.0955 (18)0.0569 (16)0.0163 (15)0.0493 (16)
C24B0.0659 (12)0.0688 (12)0.0637 (12)0.0277 (10)0.0120 (10)0.0296 (10)
C25B0.0549 (10)0.0395 (8)0.0394 (8)0.0096 (7)0.0054 (7)0.0123 (7)
C26B0.0635 (12)0.0592 (11)0.0498 (10)0.0049 (9)0.0003 (9)0.0228 (9)
C27B0.1053 (19)0.0576 (12)0.0413 (10)0.0159 (12)0.0078 (11)0.0158 (9)
C28B0.121 (2)0.0583 (12)0.0502 (12)0.0227 (13)0.0314 (13)0.0160 (10)
C29B0.0911 (17)0.120 (2)0.0652 (15)0.0518 (16)0.0356 (13)0.0357 (14)
C30B0.0608 (12)0.1007 (17)0.0489 (11)0.0267 (11)0.0119 (9)0.0226 (11)
C31B0.1061 (17)0.0621 (12)0.0659 (13)0.0031 (12)0.0242 (12)0.0391 (11)
C32B0.0637 (12)0.0713 (13)0.0570 (11)0.0140 (9)0.0185 (9)0.0381 (10)
C33B0.0754 (13)0.0701 (13)0.0615 (12)0.0215 (10)0.0187 (10)0.0368 (11)
C34B0.0642 (13)0.0769 (14)0.0745 (14)0.0231 (11)0.0230 (11)0.0256 (12)
C35B0.0570 (13)0.118 (2)0.0595 (13)0.0228 (13)0.0221 (10)0.0286 (14)
C36B0.0622 (13)0.133 (2)0.0632 (14)0.0225 (14)0.0210 (10)0.0597 (15)
C37B0.0694 (13)0.0914 (15)0.0715 (14)0.0190 (11)0.0242 (11)0.0545 (13)
C38B0.0636 (12)0.0548 (11)0.0627 (12)0.0038 (9)0.0015 (10)0.0171 (10)
C39B0.0622 (14)0.0910 (17)0.0958 (18)0.0185 (12)0.0090 (13)0.0236 (14)
N1B0.0738 (11)0.0539 (9)0.0466 (8)0.0068 (7)0.0125 (7)0.0261 (7)
N2B0.0523 (8)0.0421 (7)0.0449 (8)0.0032 (6)0.0039 (6)0.0153 (6)
O1B0.0567 (8)0.0704 (9)0.0660 (8)0.0048 (7)0.0092 (7)0.0304 (7)
O2B0.0597 (7)0.0440 (6)0.0365 (6)0.0153 (5)0.0052 (5)0.0127 (5)
O3B0.0473 (7)0.0670 (8)0.0521 (7)0.0089 (6)0.0154 (6)0.0248 (6)
O4B0.0897 (12)0.0961 (12)0.0685 (10)0.0217 (10)0.0009 (9)0.0039 (9)
C400.177 (6)0.090 (4)0.081 (4)0.035 (4)0.014 (4)0.043 (4)
C410.175 (6)0.089 (3)0.081 (3)0.013 (4)0.017 (4)0.048 (2)
N30.189 (6)0.122 (4)0.113 (3)0.014 (4)0.030 (4)0.064 (3)
C4010.162 (7)0.090 (5)0.083 (5)0.019 (5)0.021 (5)0.052 (4)
C4110.168 (7)0.096 (5)0.083 (4)0.016 (5)0.027 (5)0.042 (4)
N310.178 (7)0.116 (6)0.104 (5)0.013 (5)0.032 (5)0.048 (4)
Geometric parameters (Å, º) top
C1A—C2A1.378 (3)C3B—C4B1.370 (3)
C1A—C6A1.390 (2)C3B—H3B0.9300
C1A—N1A1.402 (2)C4B—C5B1.392 (3)
C2A—C3A1.372 (3)C4B—H4B0.9300
C2A—H2A0.9300C5B—C6B1.375 (3)
C3A—C4A1.371 (3)C5B—H5B0.9300
C3A—H3A0.9300C6B—C7B1.505 (2)
C4A—C5A1.388 (3)C7B—O2B1.4074 (18)
C4A—H4A0.9300C7B—C8B1.556 (2)
C5A—C6A1.368 (3)C7B—C11B1.596 (2)
C5A—H5A0.9300C8B—O1B1.208 (2)
C6A—C7A1.504 (2)C8B—N1B1.361 (2)
C7A—O2A1.4147 (19)C9B—O2B1.4319 (19)
C7A—C8A1.555 (2)C9B—C25B1.505 (2)
C7A—C11A1.614 (2)C9B—C10B1.551 (2)
C8A—O1A1.206 (2)C9B—H9B0.9800
C8A—N1A1.364 (2)C10B—C19B1.516 (2)
C9A—O2A1.4434 (19)C10B—C11B1.568 (2)
C9A—C25A1.505 (2)C10B—H10B0.9800
C9A—C10A1.532 (2)C11B—C12B1.512 (2)
C9A—H9A0.9800C11B—C18B1.534 (2)
C10A—C19A1.509 (2)C12B—C13B1.380 (2)
C10A—C11A1.561 (2)C12B—C17B1.393 (2)
C10A—H10A0.9800C13B—C14B1.388 (3)
C11A—C12A1.511 (2)C13B—H13B0.9300
C11A—C18A1.527 (2)C14B—C15B1.372 (3)
C12A—C13A1.379 (2)C14B—H14B0.9300
C12A—C17A1.391 (2)C15B—C16B1.379 (3)
C13A—C14A1.384 (3)C15B—H15B0.9300
C13A—H13A0.9300C16B—C17B1.383 (2)
C14A—C15A1.368 (3)C16B—H16B0.9300
C14A—H14A0.9300C17B—N2B1.425 (2)
C15A—C16A1.372 (3)C18B—O3B1.1996 (19)
C15A—H15A0.9300C18B—N2B1.406 (2)
C16A—C17A1.386 (3)C19B—C24B1.385 (3)
C16A—H16A0.9300C19B—C20B1.386 (3)
C17A—N2A1.424 (2)C20B—C21B1.383 (3)
C18A—O3A1.201 (2)C20B—H20B0.9300
C18A—N2A1.406 (2)C21B—C22B1.366 (4)
C19A—C20A1.379 (2)C21B—H21B0.9300
C19A—C24A1.387 (2)C22B—C23B1.368 (4)
C20A—C21A1.386 (3)C22B—H22B0.9300
C20A—H20A0.9300C23B—C24B1.384 (3)
C21A—C22A1.370 (3)C23B—H23B0.9300
C21A—H21A0.9300C24B—H24B0.9300
C22A—C23A1.365 (3)C25B—C26B1.372 (2)
C22A—H22A0.9300C25B—C30B1.376 (3)
C23A—C24A1.379 (3)C26B—C27B1.397 (3)
C23A—H23A0.9300C26B—H26B0.9300
C24A—H24A0.9300C27B—C28B1.355 (3)
C25A—C26A1.374 (3)C27B—H27B0.9300
C25A—C30A1.376 (3)C28B—C29B1.353 (3)
C26A—C27A1.385 (3)C28B—H28B0.9300
C26A—H26A0.9300C29B—C30B1.377 (3)
C27A—C28A1.362 (3)C29B—H29B0.9300
C27A—H27A0.9300C30B—H30B0.9300
C28A—C29A1.358 (3)C31B—N1B1.458 (2)
C28A—H28A0.9300C31B—C32B1.511 (3)
C29A—C30A1.379 (3)C31B—H31C0.9700
C29A—H29A0.9300C31B—H31D0.9700
C30A—H30A0.9300C32B—C33B1.377 (3)
C31A—N1A1.457 (2)C32B—C37B1.385 (3)
C31A—C32A1.497 (3)C33B—C34B1.375 (3)
C31A—H31A0.9700C33B—H33B0.9300
C31A—H31B0.9700C34B—C35B1.370 (3)
C32A—C33A1.367 (3)C34B—H34B0.9300
C32A—C37A1.388 (3)C35B—C36B1.366 (4)
C33A—C34A1.380 (3)C35B—H35B0.9300
C33A—H33A0.9300C36B—C37B1.378 (3)
C34A—C35A1.358 (3)C36B—H36B0.9300
C34A—H34A0.9300C37B—H37B0.9300
C35A—C36A1.360 (4)C38B—O4B1.199 (2)
C35A—H35A0.9300C38B—N2B1.413 (2)
C36A—C37A1.373 (3)C38B—C39B1.485 (3)
C36A—H36A0.9300C39B—H39D0.9600
C37A—H37A0.9300C39B—H39E0.9600
C38A—O4A1.204 (3)C39B—H39F0.9600
C38A—N2A1.412 (3)C40—C411.425 (11)
C38A—C39A1.476 (4)C40—H40A0.9600
C39A—H39A0.9600C40—H40B0.9600
C39A—H39B0.9600C40—H40C0.9600
C39A—H39C0.9600C41—N31.127 (9)
C1B—C2B1.376 (3)C401—C4111.485 (17)
C1B—C6B1.387 (2)C401—H40D0.9600
C1B—N1B1.408 (2)C401—H40E0.9600
C2B—C3B1.371 (3)C401—H40F0.9600
C2B—H2B0.9300C411—N311.128 (15)
C2A—C1A—C6A121.93 (19)C4B—C3B—H3B119.2
C2A—C1A—N1A127.99 (18)C2B—C3B—H3B119.2
C6A—C1A—N1A109.97 (15)C3B—C4B—C5B120.5 (2)
C3A—C2A—C1A117.6 (2)C3B—C4B—H4B119.7
C3A—C2A—H2A121.2C5B—C4B—H4B119.7
C1A—C2A—H2A121.2C6B—C5B—C4B118.40 (19)
C4A—C3A—C2A121.3 (2)C6B—C5B—H5B120.8
C4A—C3A—H3A119.4C4B—C5B—H5B120.8
C2A—C3A—H3A119.4C5B—C6B—C1B120.01 (16)
C3A—C4A—C5A120.7 (2)C5B—C6B—C7B131.15 (16)
C3A—C4A—H4A119.6C1B—C6B—C7B108.66 (15)
C5A—C4A—H4A119.6O2B—C7B—C6B110.38 (13)
C6A—C5A—C4A118.90 (19)O2B—C7B—C8B111.72 (13)
C6A—C5A—H5A120.6C6B—C7B—C8B101.88 (13)
C4A—C5A—H5A120.6O2B—C7B—C11B104.88 (12)
C5A—C6A—C1A119.45 (17)C6B—C7B—C11B118.19 (13)
C5A—C6A—C7A131.81 (16)C8B—C7B—C11B109.94 (13)
C1A—C6A—C7A108.63 (15)O1B—C8B—N1B126.59 (17)
O2A—C7A—C6A111.09 (13)O1B—C8B—C7B125.91 (16)
O2A—C7A—C8A110.17 (13)N1B—C8B—C7B107.50 (15)
C6A—C7A—C8A101.73 (13)O2B—C9B—C25B107.71 (13)
O2A—C7A—C11A105.43 (12)O2B—C9B—C10B105.40 (12)
C6A—C7A—C11A117.74 (14)C25B—C9B—C10B114.39 (13)
C8A—C7A—C11A110.66 (12)O2B—C9B—H9B109.7
O1A—C8A—N1A125.92 (17)C25B—C9B—H9B109.7
O1A—C8A—C7A126.73 (16)C10B—C9B—H9B109.7
N1A—C8A—C7A107.33 (15)C19B—C10B—C9B114.46 (13)
O2A—C9A—C25A108.70 (13)C19B—C10B—C11B118.57 (13)
O2A—C9A—C10A102.21 (13)C9B—C10B—C11B104.63 (12)
C25A—C9A—C10A115.24 (14)C19B—C10B—H10B106.1
O2A—C9A—H9A110.1C9B—C10B—H10B106.1
C25A—C9A—H9A110.1C11B—C10B—H10B106.1
C10A—C9A—H9A110.1C12B—C11B—C18B101.56 (12)
C19A—C10A—C9A116.95 (13)C12B—C11B—C10B122.99 (13)
C19A—C10A—C11A118.33 (13)C18B—C11B—C10B108.99 (12)
C9A—C10A—C11A103.85 (13)C12B—C11B—C7B113.15 (12)
C19A—C10A—H10A105.5C18B—C11B—C7B106.36 (12)
C9A—C10A—H10A105.5C10B—C11B—C7B102.87 (11)
C11A—C10A—H10A105.5C13B—C12B—C17B119.13 (15)
C12A—C11A—C18A101.70 (13)C13B—C12B—C11B131.46 (15)
C12A—C11A—C10A121.02 (13)C17B—C12B—C11B109.39 (14)
C18A—C11A—C10A109.68 (13)C12B—C13B—C14B119.50 (18)
C12A—C11A—C7A114.18 (13)C12B—C13B—H13B120.3
C18A—C11A—C7A108.42 (13)C14B—C13B—H13B120.3
C10A—C11A—C7A101.55 (12)C15B—C14B—C13B120.41 (19)
C13A—C12A—C17A119.06 (16)C15B—C14B—H14B119.8
C13A—C12A—C11A131.61 (16)C13B—C14B—H14B119.8
C17A—C12A—C11A109.32 (15)C14B—C15B—C16B121.30 (18)
C12A—C13A—C14A119.28 (19)C14B—C15B—H15B119.4
C12A—C13A—H13A120.4C16B—C15B—H15B119.3
C14A—C13A—H13A120.4C15B—C16B—C17B118.00 (18)
C15A—C14A—C13A120.7 (2)C15B—C16B—H16B121.0
C15A—C14A—H14A119.6C17B—C16B—H16B121.0
C13A—C14A—H14A119.6C16B—C17B—C12B121.65 (17)
C14A—C15A—C16A121.42 (19)C16B—C17B—N2B128.47 (17)
C14A—C15A—H15A119.3C12B—C17B—N2B109.83 (14)
C16A—C15A—H15A119.3O3B—C18B—N2B126.06 (15)
C15A—C16A—C17A117.7 (2)O3B—C18B—C11B125.69 (15)
C15A—C16A—H16A121.1N2B—C18B—C11B108.25 (13)
C17A—C16A—H16A121.1C24B—C19B—C20B117.99 (17)
C16A—C17A—C12A121.77 (19)C24B—C19B—C10B118.93 (16)
C16A—C17A—N2A128.54 (18)C20B—C19B—C10B123.03 (17)
C12A—C17A—N2A109.58 (15)C21B—C20B—C19B120.7 (2)
O3A—C18A—N2A126.33 (17)C21B—C20B—H20B119.7
O3A—C18A—C11A125.75 (17)C19B—C20B—H20B119.7
N2A—C18A—C11A107.91 (15)C22B—C21B—C20B120.6 (2)
C20A—C19A—C24A117.74 (16)C22B—C21B—H21B119.7
C20A—C19A—C10A123.55 (15)C20B—C21B—H21B119.7
C24A—C19A—C10A118.62 (15)C21B—C22B—C23B119.7 (2)
C19A—C20A—C21A120.96 (17)C21B—C22B—H22B120.2
C19A—C20A—H20A119.5C23B—C22B—H22B120.2
C21A—C20A—H20A119.5C22B—C23B—C24B120.2 (3)
C22A—C21A—C20A120.33 (19)C22B—C23B—H23B119.9
C22A—C21A—H21A119.8C24B—C23B—H23B119.9
C20A—C21A—H21A119.8C23B—C24B—C19B120.9 (2)
C23A—C22A—C21A119.40 (19)C23B—C24B—H24B119.6
C23A—C22A—H22A120.3C19B—C24B—H24B119.6
C21A—C22A—H22A120.3C26B—C25B—C30B118.13 (17)
C22A—C23A—C24A120.56 (19)C26B—C25B—C9B120.90 (16)
C22A—C23A—H23A119.7C30B—C25B—C9B120.96 (15)
C24A—C23A—H23A119.7C25B—C26B—C27B120.5 (2)
C23A—C24A—C19A120.98 (18)C25B—C26B—H26B119.7
C23A—C24A—H24A119.5C27B—C26B—H26B119.7
C19A—C24A—H24A119.5C28B—C27B—C26B120.08 (19)
C26A—C25A—C30A118.58 (17)C28B—C27B—H27B120.0
C26A—C25A—C9A120.10 (17)C26B—C27B—H27B120.0
C30A—C25A—C9A121.32 (16)C29B—C28B—C27B119.8 (2)
C25A—C26A—C27A120.4 (2)C29B—C28B—H28B120.1
C25A—C26A—H26A119.8C27B—C28B—H28B120.1
C27A—C26A—H26A119.8C28B—C29B—C30B120.8 (2)
C28A—C27A—C26A120.4 (2)C28B—C29B—H29B119.6
C28A—C27A—H27A119.8C30B—C29B—H29B119.6
C26A—C27A—H27A119.8C25B—C30B—C29B120.7 (2)
C29A—C28A—C27A119.6 (2)C25B—C30B—H30B119.6
C29A—C28A—H28A120.2C29B—C30B—H30B119.6
C27A—C28A—H28A120.2N1B—C31B—C32B113.30 (16)
C28A—C29A—C30A120.6 (2)N1B—C31B—H31C108.9
C28A—C29A—H29A119.7C32B—C31B—H31C108.9
C30A—C29A—H29A119.7N1B—C31B—H31D108.9
C25A—C30A—C29A120.5 (2)C32B—C31B—H31D108.9
C25A—C30A—H30A119.8H31C—C31B—H31D107.7
C29A—C30A—H30A119.8C33B—C32B—C37B118.51 (19)
N1A—C31A—C32A114.58 (16)C33B—C32B—C31B122.05 (17)
N1A—C31A—H31A108.6C37B—C32B—C31B119.44 (19)
C32A—C31A—H31A108.6C34B—C33B—C32B120.6 (2)
N1A—C31A—H31B108.6C34B—C33B—H33B119.7
C32A—C31A—H31B108.6C32B—C33B—H33B119.7
H31A—C31A—H31B107.6C35B—C34B—C33B120.3 (2)
C33A—C32A—C37A118.19 (19)C35B—C34B—H34B119.9
C33A—C32A—C31A122.14 (16)C33B—C34B—H34B119.9
C37A—C32A—C31A119.55 (18)C36B—C35B—C34B120.0 (2)
C32A—C33A—C34A120.68 (19)C36B—C35B—H35B120.0
C32A—C33A—H33A119.7C34B—C35B—H35B120.0
C34A—C33A—H33A119.7C35B—C36B—C37B119.9 (2)
C35A—C34A—C33A120.4 (2)C35B—C36B—H36B120.0
C35A—C34A—H34A119.8C37B—C36B—H36B120.0
C33A—C34A—H34A119.8C36B—C37B—C32B120.7 (2)
C34A—C35A—C36A119.9 (2)C36B—C37B—H37B119.6
C34A—C35A—H35A120.0C32B—C37B—H37B119.6
C36A—C35A—H35A120.0O4B—C38B—N2B118.9 (2)
C35A—C36A—C37A120.1 (2)O4B—C38B—C39B122.5 (2)
C35A—C36A—H36A119.9N2B—C38B—C39B118.58 (18)
C37A—C36A—H36A119.9C38B—C39B—H39D109.5
C36A—C37A—C32A120.7 (2)C38B—C39B—H39E109.5
C36A—C37A—H37A119.7H39D—C39B—H39E109.5
C32A—C37A—H37A119.7C38B—C39B—H39F109.5
O4A—C38A—N2A118.8 (3)H39D—C39B—H39F109.5
O4A—C38A—C39A123.8 (2)H39E—C39B—H39F109.5
N2A—C38A—C39A117.5 (3)C8B—N1B—C1B111.15 (15)
C38A—C39A—H39A109.5C8B—N1B—C31B123.50 (17)
C38A—C39A—H39B109.5C1B—N1B—C31B124.62 (17)
H39A—C39A—H39B109.5C18B—N2B—C38B126.07 (16)
C38A—C39A—H39C109.5C18B—N2B—C17B109.15 (13)
H39A—C39A—H39C109.5C38B—N2B—C17B124.76 (15)
H39B—C39A—H39C109.5C7B—O2B—C9B109.27 (12)
C8A—N1A—C1A111.31 (14)C41—C40—H40A109.5
C8A—N1A—C31A122.81 (17)C41—C40—H40B109.5
C1A—N1A—C31A124.22 (16)H40A—C40—H40B109.5
C18A—N2A—C38A126.30 (19)C41—C40—H40C109.5
C18A—N2A—C17A109.28 (14)H40A—C40—H40C109.5
C38A—N2A—C17A124.35 (19)H40B—C40—H40C109.5
C7A—O2A—C9A107.61 (12)N3—C41—C40178.2 (12)
C2B—C1B—C6B121.57 (19)C411—C401—H40D109.5
C2B—C1B—N1B128.27 (18)C411—C401—H40E109.5
C6B—C1B—N1B110.06 (15)H40D—C401—H40E109.5
C3B—C2B—C1B117.80 (19)C411—C401—H40F109.5
C3B—C2B—H2B121.1H40D—C401—H40F109.5
C1B—C2B—H2B121.1H40E—C401—H40F109.5
C4B—C3B—C2B121.62 (19)N31—C411—C401175 (3)
C6A—C1A—C2A—C3A3.4 (3)C6B—C1B—C2B—C3B1.6 (3)
N1A—C1A—C2A—C3A172.3 (2)N1B—C1B—C2B—C3B174.53 (18)
C1A—C2A—C3A—C4A0.4 (4)C1B—C2B—C3B—C4B1.0 (3)
C2A—C3A—C4A—C5A1.9 (5)C2B—C3B—C4B—C5B1.8 (3)
C3A—C4A—C5A—C6A1.2 (4)C3B—C4B—C5B—C6B0.1 (3)
C4A—C5A—C6A—C1A1.7 (3)C4B—C5B—C6B—C1B2.4 (3)
C4A—C5A—C6A—C7A177.3 (2)C4B—C5B—C6B—C7B176.96 (17)
C2A—C1A—C6A—C5A4.1 (3)C2B—C1B—C6B—C5B3.3 (3)
N1A—C1A—C6A—C5A172.28 (18)N1B—C1B—C6B—C5B173.44 (15)
C2A—C1A—C6A—C7A179.33 (18)C2B—C1B—C6B—C7B178.96 (16)
N1A—C1A—C6A—C7A4.3 (2)N1B—C1B—C6B—C7B2.23 (19)
C5A—C6A—C7A—O2A50.2 (3)C5B—C6B—C7B—O2B49.8 (2)
C1A—C6A—C7A—O2A125.79 (16)C1B—C6B—C7B—O2B125.18 (14)
C5A—C6A—C7A—C8A167.4 (2)C5B—C6B—C7B—C8B168.62 (17)
C1A—C6A—C7A—C8A8.56 (18)C1B—C6B—C7B—C8B6.39 (17)
C5A—C6A—C7A—C11A71.5 (3)C5B—C6B—C7B—C11B70.8 (2)
C1A—C6A—C7A—C11A112.54 (17)C1B—C6B—C7B—C11B114.15 (16)
O2A—C7A—C8A—O1A50.2 (2)O2B—C7B—C8B—O1B53.4 (2)
C6A—C7A—C8A—O1A168.12 (17)C6B—C7B—C8B—O1B171.25 (17)
C11A—C7A—C8A—O1A66.0 (2)C11B—C7B—C8B—O1B62.6 (2)
O2A—C7A—C8A—N1A128.04 (14)O2B—C7B—C8B—N1B126.40 (14)
C6A—C7A—C8A—N1A10.14 (17)C6B—C7B—C8B—N1B8.56 (17)
C11A—C7A—C8A—N1A115.76 (15)C11B—C7B—C8B—N1B117.59 (15)
O2A—C9A—C10A—C19A170.70 (12)O2B—C9B—C10B—C19B151.19 (13)
C25A—C9A—C10A—C19A71.61 (18)C25B—C9B—C10B—C19B90.69 (17)
O2A—C9A—C10A—C11A38.35 (15)O2B—C9B—C10B—C11B19.76 (15)
C25A—C9A—C10A—C11A156.04 (13)C25B—C9B—C10B—C11B137.89 (14)
C19A—C10A—C11A—C12A22.5 (2)C19B—C10B—C11B—C12B0.8 (2)
C9A—C10A—C11A—C12A109.04 (16)C9B—C10B—C11B—C12B129.78 (15)
C19A—C10A—C11A—C18A95.30 (17)C19B—C10B—C11B—C18B119.22 (15)
C9A—C10A—C11A—C18A133.17 (14)C9B—C10B—C11B—C18B111.78 (14)
C19A—C10A—C11A—C7A150.15 (14)C19B—C10B—C11B—C7B128.19 (15)
C9A—C10A—C11A—C7A18.61 (15)C9B—C10B—C11B—C7B0.81 (15)
O2A—C7A—C11A—C12A139.34 (14)O2B—C7B—C11B—C12B156.30 (13)
C6A—C7A—C11A—C12A96.12 (17)C6B—C7B—C11B—C12B80.24 (18)
C8A—C7A—C11A—C12A20.23 (18)C8B—C7B—C11B—C12B36.05 (17)
O2A—C7A—C11A—C18A108.09 (14)O2B—C7B—C11B—C18B93.05 (14)
C6A—C7A—C11A—C18A16.44 (18)C6B—C7B—C11B—C18B30.41 (18)
C8A—C7A—C11A—C18A132.80 (14)C8B—C7B—C11B—C18B146.71 (13)
O2A—C7A—C11A—C10A7.39 (15)O2B—C7B—C11B—C10B21.47 (15)
C6A—C7A—C11A—C10A131.93 (14)C6B—C7B—C11B—C10B144.93 (14)
C8A—C7A—C11A—C10A111.71 (14)C8B—C7B—C11B—C10B98.77 (14)
C18A—C11A—C12A—C13A168.43 (18)C18B—C11B—C12B—C13B170.33 (17)
C10A—C11A—C12A—C13A46.7 (3)C10B—C11B—C12B—C13B48.4 (3)
C7A—C11A—C12A—C13A75.0 (2)C7B—C11B—C12B—C13B76.1 (2)
C18A—C11A—C12A—C17A12.18 (17)C18B—C11B—C12B—C17B11.33 (16)
C10A—C11A—C12A—C17A133.90 (16)C10B—C11B—C12B—C17B133.26 (15)
C7A—C11A—C12A—C17A104.35 (16)C7B—C11B—C12B—C17B102.26 (15)
C17A—C12A—C13A—C14A0.0 (3)C17B—C12B—C13B—C14B0.9 (3)
C11A—C12A—C13A—C14A179.37 (17)C11B—C12B—C13B—C14B177.30 (17)
C12A—C13A—C14A—C15A1.2 (3)C12B—C13B—C14B—C15B0.2 (3)
C13A—C14A—C15A—C16A1.2 (3)C13B—C14B—C15B—C16B0.8 (3)
C14A—C15A—C16A—C17A0.1 (3)C14B—C15B—C16B—C17B0.3 (3)
C15A—C16A—C17A—C12A1.3 (3)C15B—C16B—C17B—C12B0.8 (3)
C15A—C16A—C17A—N2A174.41 (19)C15B—C16B—C17B—N2B176.13 (17)
C13A—C12A—C17A—C16A1.2 (3)C13B—C12B—C17B—C16B1.4 (3)
C11A—C12A—C17A—C16A178.23 (16)C11B—C12B—C17B—C16B177.18 (15)
C13A—C12A—C17A—N2A175.18 (15)C13B—C12B—C17B—N2B176.03 (15)
C11A—C12A—C17A—N2A5.34 (19)C11B—C12B—C17B—N2B5.40 (18)
C12A—C11A—C18A—O3A166.16 (18)C12B—C11B—C18B—O3B167.17 (16)
C10A—C11A—C18A—O3A36.9 (2)C10B—C11B—C18B—O3B36.0 (2)
C7A—C11A—C18A—O3A73.2 (2)C7B—C11B—C18B—O3B74.26 (19)
C12A—C11A—C18A—N2A14.86 (17)C12B—C11B—C18B—N2B13.48 (16)
C10A—C11A—C18A—N2A144.13 (14)C10B—C11B—C18B—N2B144.64 (13)
C7A—C11A—C18A—N2A105.80 (15)C7B—C11B—C18B—N2B105.08 (14)
C9A—C10A—C19A—C20A36.2 (2)C9B—C10B—C19B—C24B135.80 (16)
C11A—C10A—C19A—C20A89.18 (19)C11B—C10B—C19B—C24B99.90 (18)
C9A—C10A—C19A—C24A140.47 (16)C9B—C10B—C19B—C20B41.4 (2)
C11A—C10A—C19A—C24A94.14 (18)C11B—C10B—C19B—C20B82.9 (2)
C24A—C19A—C20A—C21A1.8 (3)C24B—C19B—C20B—C21B0.8 (3)
C10A—C19A—C20A—C21A178.49 (16)C10B—C19B—C20B—C21B178.00 (18)
C19A—C20A—C21A—C22A1.8 (3)C19B—C20B—C21B—C22B0.6 (3)
C20A—C21A—C22A—C23A0.6 (3)C20B—C21B—C22B—C23B0.2 (4)
C21A—C22A—C23A—C24A0.5 (3)C21B—C22B—C23B—C24B0.7 (4)
C22A—C23A—C24A—C19A0.4 (3)C22B—C23B—C24B—C19B0.5 (4)
C20A—C19A—C24A—C23A0.7 (3)C20B—C19B—C24B—C23B0.2 (3)
C10A—C19A—C24A—C23A177.54 (17)C10B—C19B—C24B—C23B177.60 (19)
O2A—C9A—C25A—C26A120.18 (18)O2B—C9B—C25B—C26B146.23 (16)
C10A—C9A—C25A—C26A125.84 (18)C10B—C9B—C25B—C26B96.97 (19)
O2A—C9A—C25A—C30A58.9 (2)O2B—C9B—C25B—C30B33.8 (2)
C10A—C9A—C25A—C30A55.1 (2)C10B—C9B—C25B—C30B83.0 (2)
C30A—C25A—C26A—C27A0.6 (3)C30B—C25B—C26B—C27B0.1 (3)
C9A—C25A—C26A—C27A179.8 (2)C9B—C25B—C26B—C27B179.99 (17)
C25A—C26A—C27A—C28A0.9 (4)C25B—C26B—C27B—C28B0.2 (3)
C26A—C27A—C28A—C29A0.4 (4)C26B—C27B—C28B—C29B0.1 (4)
C27A—C28A—C29A—C30A0.3 (4)C27B—C28B—C29B—C30B0.4 (4)
C26A—C25A—C30A—C29A0.1 (3)C26B—C25B—C30B—C29B0.5 (3)
C9A—C25A—C30A—C29A179.06 (18)C9B—C25B—C30B—C29B179.6 (2)
C28A—C29A—C30A—C25A0.5 (3)C28B—C29B—C30B—C25B0.7 (4)
N1A—C31A—C32A—C33A21.3 (3)N1B—C31B—C32B—C33B34.0 (3)
N1A—C31A—C32A—C37A162.68 (18)N1B—C31B—C32B—C37B146.8 (2)
C37A—C32A—C33A—C34A1.1 (3)C37B—C32B—C33B—C34B0.2 (3)
C31A—C32A—C33A—C34A175.0 (2)C31B—C32B—C33B—C34B179.0 (2)
C32A—C33A—C34A—C35A0.4 (4)C32B—C33B—C34B—C35B0.1 (3)
C33A—C34A—C35A—C36A0.7 (4)C33B—C34B—C35B—C36B0.0 (3)
C34A—C35A—C36A—C37A1.0 (4)C34B—C35B—C36B—C37B0.3 (3)
C35A—C36A—C37A—C32A0.2 (4)C35B—C36B—C37B—C32B0.6 (3)
C33A—C32A—C37A—C36A0.8 (3)C33B—C32B—C37B—C36B0.6 (3)
C31A—C32A—C37A—C36A175.4 (2)C31B—C32B—C37B—C36B178.6 (2)
O1A—C8A—N1A—C1A169.93 (17)O1B—C8B—N1B—C1B171.97 (18)
C7A—C8A—N1A—C1A8.35 (19)C7B—C8B—N1B—C1B7.84 (18)
O1A—C8A—N1A—C31A4.1 (3)O1B—C8B—N1B—C31B1.4 (3)
C7A—C8A—N1A—C31A174.22 (15)C7B—C8B—N1B—C31B178.45 (16)
C2A—C1A—N1A—C8A173.3 (2)C2B—C1B—N1B—C8B172.69 (18)
C6A—C1A—N1A—C8A2.8 (2)C6B—C1B—N1B—C8B3.8 (2)
C2A—C1A—N1A—C31A7.7 (3)C2B—C1B—N1B—C31B2.2 (3)
C6A—C1A—N1A—C31A168.44 (17)C6B—C1B—N1B—C31B174.24 (17)
C32A—C31A—N1A—C8A109.3 (2)C32B—C31B—N1B—C8B128.2 (2)
C32A—C31A—N1A—C1A86.6 (2)C32B—C31B—N1B—C1B62.4 (3)
O3A—C18A—N2A—C38A14.7 (3)O3B—C18B—N2B—C38B12.2 (3)
C11A—C18A—N2A—C38A164.3 (2)C11B—C18B—N2B—C38B167.18 (16)
O3A—C18A—N2A—C17A168.39 (19)O3B—C18B—N2B—C17B169.51 (16)
C11A—C18A—N2A—C17A12.64 (19)C11B—C18B—N2B—C17B11.14 (17)
O4A—C38A—N2A—C18A162.4 (2)O4B—C38B—N2B—C18B171.1 (2)
C39A—C38A—N2A—C18A16.8 (4)C39B—C38B—N2B—C18B8.2 (3)
O4A—C38A—N2A—C17A14.2 (4)O4B—C38B—N2B—C17B6.9 (3)
C39A—C38A—N2A—C17A166.7 (3)C39B—C38B—N2B—C17B173.77 (19)
C16A—C17A—N2A—C18A171.40 (19)C16B—C17B—N2B—C18B173.46 (17)
C12A—C17A—N2A—C18A4.7 (2)C12B—C17B—N2B—C18B3.74 (18)
C16A—C17A—N2A—C38A11.6 (3)C16B—C17B—N2B—C38B8.2 (3)
C12A—C17A—N2A—C38A172.3 (2)C12B—C17B—N2B—C38B174.61 (16)
C6A—C7A—O2A—C9A161.66 (14)C6B—C7B—O2B—C9B164.71 (13)
C8A—C7A—O2A—C9A86.38 (15)C8B—C7B—O2B—C9B82.68 (16)
C11A—C7A—O2A—C9A33.05 (16)C11B—C7B—O2B—C9B36.38 (15)
C25A—C9A—O2A—C7A167.77 (13)C25B—C9B—O2B—C7B158.62 (13)
C10A—C9A—O2A—C7A45.49 (15)C10B—C9B—O2B—C7B36.10 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5A—H5A···O3A0.932.522.974 (3)111
C5B—H5B···O3B0.932.503.086 (2)121
C9A—H9A···O1A0.982.523.122 (2)119
C9B—H9B···O1B0.982.603.107 (2)113
C10A—H10A···O3A0.982.382.900 (2)113
C10B—H10B···O3B0.982.382.8883 (19)111
C13A—H13A···O1A0.932.522.911 (2)106
C13B—H13B···O1B0.932.533.033 (2)114
C16A—H16A···O4A0.932.342.856 (3)115
C16B—H16B···O4B0.932.292.830 (3)117
C27B—H27B···O1Bi0.932.463.308 (3)151
C31A—H31A···O1A0.972.502.872 (3)103
C31B—H31D···O1B0.972.512.896 (3)103
C34A—H34A···O4Aii0.932.503.387 (4)159
C3B—H3B···Cg1(C19A–C24A)iii0.932.993.472 (2)114
C24B—H24B···Cg2(C32A–C37A)iv0.932.833.637 (2)146
C39A—H39C···Cg2(C32A–C37A)iv0.962.843.690 (4)148
C33A—H33A···Cg3(C12A–C17A)0.932.753.578 (2)149
C33B—H33B···Cg4(C12B–C17B)0.932.773.680 (3)165
Symmetry codes: (i) x, y+1, z+1; (ii) x+2, y+2, z+1; (iii) x, y, z+1; (iv) x1, y, z.

Experimental details

(I)(II)(III)(IV)
Crystal data
Chemical formulaC44H33ClN2O3C39H29ClN2O4C39H30N2O4C39H30N2O4·0.5C2H3N
Mr673.17625.09590.65611.18
Crystal system, space groupTriclinic, P1Triclinic, P1Triclinic, P1Triclinic, P1
Temperature (K)294294294294
a, b, c (Å)10.1099 (10), 11.3367 (11), 17.0315 (17)11.9830 (5), 12.9260 (6), 21.5664 (10)9.7565 (10), 16.6868 (16), 19.9593 (19)9.6940 (5), 18.581 (1), 20.1552 (11)
α, β, γ (°)74.755 (2), 78.503 (2), 65.557 (2)76.330 (1), 76.522 (1), 77.553 (1)71.653 (2), 81.657 (2), 89.314 (2)114.872 (2), 98.465 (2), 99.397 (2)
V3)1705.4 (3)3110.6 (2)3049.7 (5)3153.6 (3)
Z2444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.160.170.080.08
Crystal size (mm)0.15 × 0.08 × 0.060.13 × 0.11 × 0.060.11 × 0.08 × 0.060.18 × 0.08 × 0.07
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Bruker SMART APEX CCD area-detector
diffractometer
Bruker SMART APEX CCD area-detector
diffractometer
Bruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Multi-scan
(SADABS; Bruker, 2001)
Multi-scan
(SADABS; Bruker, 2001)
Multi-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.92, 0.980.94, 0.970.96, 0.990.97, 0.99
No. of measured, independent and
observed [I > 2σ(I)] reflections
20091, 8008, 6578 36879, 14644, 8962 29800, 10763, 6882 37306, 14817, 10357
Rint0.0200.0340.0360.023
(sin θ/λ)max1)0.6670.6680.5950.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.155, 1.13 0.068, 0.160, 1.04 0.070, 0.149, 1.09 0.058, 0.147, 1.01
No. of reflections8008146441076314817
No. of parameters451831813870
No. of restraints00070
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.170.27, 0.190.22, 0.170.27, 0.16

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXS97 (Sheldrick, 2015), SHELXL2014 (Sheldrick, 2015), DIAMOND (Brandenburg & Putz, 2005) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O30.932.553.067 (2)116
C9—H9···O10.982.603.115 (2)113
C10—H10···O30.982.452.951 (2)111
C13—H13···O10.932.403.011 (3)123
C31—H31B···O10.972.532.914 (3)104
C38—H38A···O30.972.512.881 (3)103
C31—H31A···O2i0.972.613.417 (2)141
C3—H3···Cg1(C32–C37)ii0.932.903.734 (2)149
C27—H27···Cg2(C1–C6)iii0.932.913.537 (2)126
C33—H33···Cg3(C12–C17)0.932.903.560 (2)147
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+1, y+2, z+1; (iii) x+1, y, z.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
C5A—H5A···O3A0.932.573.157 (3)122
C5B—H5B···O3B0.932.563.118 (4)119
C9A—H9A···O1A0.982.693.152 (3)109
C9B—H9B···O1B0.982.533.088 (3)116
C10A—H10A···O3A0.982.392.881 (3)111
C10B—H10B···O3B0.982.342.871 (3)113
C13A—H13A···O1A0.932.643.157 (3)115
C13B—H13B···O1B0.932.493.003 (3)115
C16A—H16A···O4A0.932.302.840 (4)117
C16B—H16B···O4B0.932.292.835 (5)117
C20A—H20A···O1A0.932.433.256 (3)148
C20B—H20B···O1B0.932.703.515 (3)147
C27B—H27B···O1Ai0.932.593.374 (3)142
C30A—H30A···O3A0.932.473.314 (3)151
C30B—H30B···O3B0.932.853.701 (3)153
C31A—H31A···O1A0.972.532.913 (3)104
C31B—H31D···O1B0.972.552.921 (3)104
C15A—H15A···Cg3(C19B–C24B)0.932.913.808 (14)163
C33A—H33A···Cg4(C12A–C17A)0.932.893.717 (3)149
C33B—H33B···Cg5(C12B–C17B)0.932.643.485 (3)151
Symmetry code: (i) x1, y+1, z.
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
C5A—H5A···O3A0.932.533.109 (4)121
C5B—H5B···O3B0.932.532.973 (4)109
C9A—H9A···O1A0.982.613.115 (3)112
C9B—H9B···O1B0.982.533.125 (3)119
C10A—H10A···O3A0.982.382.876 (3)111
C10B—H10B···O3B0.982.392.910 (3)113
C13A—H13A···O1A0.932.533.057 (4)116
C13B—H13B···O1B0.932.422.880 (4)110
C16A—H16A···O4A0.932.312.853 (6)116
C16B—H16B···O4B0.932.272.813 (5)117
C27A—H27A···O1Ai0.932.463.310 (4)152
C31A—H31A···O1A0.972.512.892 (4)103
C31B—H31D···O1B0.972.492.866 (4)103
C3A—H3A···Cg1(C19B–C24B)ii0.932.983.474 (4)115
C24A—H24A···Cg2(C32B–C37B)iii0.932.863.677 (3)147
C31B—H31C···Cg3(C25A–C30A)iv0.972.963.889 (4)161
C33A—H33A···Cg4(C12A–C17A)0.932.723.602 (4)158
C33B—H33B···Cg5(C12B–C17B)0.932.803.572 (4)142
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y+1, z; (iii) x, y, z+1; (iv) x, y, z1.
Hydrogen-bond geometry (Å, º) for (IV) top
D—H···AD—HH···AD···AD—H···A
C5A—H5A···O3A0.932.522.974 (3)111
C5B—H5B···O3B0.932.503.086 (2)121
C9A—H9A···O1A0.982.523.122 (2)119
C9B—H9B···O1B0.982.603.107 (2)113
C10A—H10A···O3A0.982.382.900 (2)113
C10B—H10B···O3B0.982.382.8883 (19)111
C13A—H13A···O1A0.932.522.911 (2)106
C13B—H13B···O1B0.932.533.033 (2)114
C16A—H16A···O4A0.932.342.856 (3)115
C16B—H16B···O4B0.932.292.830 (3)117
C27B—H27B···O1Bi0.932.463.308 (3)151
C31A—H31A···O1A0.972.502.872 (3)103
C31B—H31D···O1B0.972.512.896 (3)103
C34A—H34A···O4Aii0.932.503.387 (4)159
C3B—H3B···Cg1(C19A–C24A)iii0.932.993.472 (2)114
C24B—H24B···Cg2(C32A–C37A)iv0.932.833.637 (2)146
C39A—H39C···Cg2(C32A–C37A)iv0.962.843.690 (4)148
C33A—H33A···Cg3(C12A–C17A)0.932.753.578 (2)149
C33B—H33B···Cg4(C12B–C17B)0.932.773.680 (3)165
Symmetry codes: (i) x, y+1, z+1; (ii) x+2, y+2, z+1; (iii) x, y, z+1; (iv) x1, y, z.
 

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