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The racemic title dipyrrolo­pyrrolizine compound crystallizes from dimethyl­formamide as a disolvate, C55H39Cl2N7O6·2C3H7NO. None of the four fused heterocyclic rings is planar; one adopts an envelope conformation, two others adopt half-chair conformations and the fourth adopts a conformation inter­mediate between an envelope and a half-chair. The arrangement of the ring fusions is such as to preclude the possibility of inter­nal mirror symmetry. The three independent mol­ecular components are weakly linked by C-H...O hydrogen bonds, and the dipyrrolo­pyrrolizine mol­ecules are linked by a combination of four C-H...O and one C-H...[pi](arene) hydrogen bond to form a three-dimensional framework, from which the dimethyl­formamide solvent mol­ecules are pendent. However, aromatic [pi]-[pi] stacking inter­actions are absent in the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270112039856/sk3451sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112039856/sk3451Isup2.hkl
Contains datablock I

CCDC reference: 914650

Comment top

Multicomponent reactions are of great synthetic importance because of their high levels of simplicity, diversity and selectivity. Equally, 1,3-dipolar cycloaddition reactions between azomethinic ylides and electrodeficient alkenes are an important method for the synthesis of pyrrolidinic-type heterocyclic compounds (Zhang & Chen, 2005; Cui et al., 2011; Quiroga et al., 2011). We report here the structure of the title compound, (I), as a dimethylformamide disolvate, prepared as an example of a catalyst-free tricomponent reaction between formyl-pyrazoles, N-arylmaleimides and methyl glycinate (see Scheme 1) for the synthesis of a pyrazole-substituted dipyrrolo[3,4-a:3',4'-f]pyrrolizine, where three important heterocyclic units of known biological potential, namely pyrrole, pyrazole and pyrrolizidine, have been incorporated into this product of a double-click reaction (Radwan & El-Kashef, 1998; Ribes et al., 2009). Few compounds containing the dipyrrolo[3,4-a:3',4'-f]pyrrolizine unit have been structurally characterized; these include compound (II) (see Scheme 2) [Cambridge Structural Database (CSD; Allen, 2002) refcode YARPUD; Gan, 2005] and several of its analogues containing additional ester groups on the molecular periphery (CSD refcodes YARQAK, YARQEO and YARQIS; Gan, 2005), and compound (III), which crystallizes as a 1:1 toluene solvate (CSD refcode GAWCUE; Cui et al., 2012).

The heterocyclic component methyl (3aRS,3cRS,6cSR,7RS,8RS,8aSR)-2,5-bis(4-chlorophenyl)-7,9-bis(1,3-diphenyl-1H-pyrazol-4-yl)-1,3,4,6-tetraoxododecahydro-1H-dipyrrolo[3,4-a:3',4'-f]pyrrolizine-3b-carboxylate, (A) (see Scheme 1), crystallizes from dimethylformamide solution as the disolvate, (I) (Fig. 1), and the three independent molecular components are weakly linked by C—H···O hydrogen bonds (Table 2). The constitution of the dipyrrolopyrrolizine component (A) is such that, with an appropriate arrangement of the ring-fusion geometry, it could in principle exhibit mirror symmetry across the plane through atoms N7a, C3b and C31 (see Scheme 1 and Fig. 1). In such circumstances, the members of each of the corresponding pairs of stereogenic centres in the two halves of the molecule would be of opposite configuration. In the event, the ring-fusion geometry is such that the two members of each pair have the same configuration. Thus, in the selected reference molecule, atoms C3a, C3c, C7 and C8 all have the R configuration, while atoms C6a and C8a both have the S configuration. This alone is sufficient to preclude any internal molecular symmetry. In addition, the torsion angles defining the orientations of the substituents at atoms N2 and N5, and at C7 and C8, together with those defining the orientation of the unsubstituted phenyl rings (Table 1), are significantly different between the two halves of the molecule. Finally, the orientation of the ester component is such that atoms O31 and O32 are displaced from the plane through atoms N7a, C3b and C31. Despite the presence of six stereogenic centres in the dipyrrolopyrrolizine molecule, this component is in fact racemic, as shown by the centrosymmetric space group.

None of the four fused rings is planar. The ring-puckering parameters (Cremer & Pople, 1975; Table 3) indicate that the ring containing atom C1 adopts a conformation very close to the envelope form, where the idealized value of ϕ2 is (36 × k)°, with the ring folded across the vector C1···C3a; the rings containing atoms C6 and C7 both adopt half-chair conformations, where the idealized value of ϕ2 is (18 + 36 x k)°; and the ring containing atom C8 adopts a conformation intermediate between the envelope and half-chair forms. These observations again preclude the possibility of any internal symmetry.

As noted above, the independent molecular components are weakly linked by C—H···O hydrogen bonds. However, atom O91 acts only as a single acceptor of hydrogen bonds, while atom O94 acts as a double acceptor (Table 2), forming an R21(6) (Bernstein et al., 1995) motif. Apart from these interactions, the dimethylformamide molecules do not participate in any other hydrogen bonds and hence they play no significant part in the supramolecular aggregation. On the basis of both the sparsity and the weakness of the C—H···O interactions involving the dimethylformamide molecules, it seems likely that they play an essentially passive role, simply occupying what would otherwise be empty spaces in the supramolecular structure defined by the dipyrrolopyrrolizine molecules, and interacting with this structure via little more than adventitious intermolecular contacts.

The heterocyclic molecules of (I) are linked into a three-dimensional framework structure of some complexity by a combination of C—H···O and C—H···π(arene) hydrogen bonds (Table 2), but the formation of the framework is readily analysed in terms of three one-dimensional substructures (Ferguson et al., 1998a,b; Gregson et al., 2000). In the analysis of the intermolecular interactions, C—H···O contacts in which the D—H···A angle is less than 140° have been discounted (Wood et al., 2009), aside from those noted earlier involving the dimethylformamide components, as have those involving C—H bonds in methyl groups. The C—H···O interaction involving atom C835 as the donor has a C—H···O angle of only 141° and so it is probably of fairly marginal significance (Wood et al., 2009). Its effect, if it were to be regarded as structurally significant, would simply be to reinforce the action of the near-linear hydrogen bond having atom C53 as the donor. Accordingly, this interaction need not be considered further in the description of the framework formation. It is interesting to note here that, despite the presence of six independent aryl groups, the crystal structure of (I) exhibits no aromatic ππ stacking interactions.

In the first substructure, a combination of two C—H···O hydrogen bonds, both involving atom O1 as the acceptor, and the C—H···π(arene) hydrogen bond link inversion-related molecules to generate a chain of rings running parallel to the [100] direction. Inversion-related pairs of C—H···O hydrogen bonds generate an R22(24) motif, and rings of this type, centred at (n+1/2, 1/2, 1/2), alternate with rings centred at (n, 1/2, 1/2), where n represents an integer in both cases, which are generated by inversion-related pairs of C—H···π(arene) hydrogen bonds (Fig. 2).

In the second substructure, a combination of two C—H···O hydrogen bonds, the donors of which both form part of the C51–C56 ring, link inversion-related molecules to form a chain of rings running parallel to the [010] direction, in which R22(14) rings centred at (1/2, n, 1/2) alternate with R22(24) rings centred at (1/2, n+1/2, 1/2), where n represents an integer in each case (Fig. 3).

In the final substructure, a combination of three C—H···O hydrogen bonds, two having atom O1 as the acceptor and the third having atom O3 as the acceptor, link inversion-related molecules to form a chain of rings running parallel to the [111] direction. In this chain, R22(24) centred at (n+1/2, 1/2-n, n+1/2) alternate with R22(26) rings centred at (n, 1-n, n), where n represents an integer in each case (Fig. 4). The combination of these three chains of rings, along [100], [010] and [111], respectively, all built from dipyrrolopyrrolizine molecules from which the dimethylformamide molecules are simply pendent, then generates a single three-dimensional framework structure.

Related literature top

For related literature, see: Allen (2002); Bernstein et al. (1995); Cremer & Pople (1975); Cui et al. (2011, 2012); Ferguson et al. (1998a, 1998b); Gan (2005); Gregson et al. (2000); Quiroga et al. (2011); Radwan & El-Kashef (1998); Ribes et al. (2009); Wood et al. (2009); Zhang & Chen (2005).

Experimental top

A mixture of 1,3-diphenyl-1H-pyrazole-4-carbaldehyde (0.2 mmol), N-(4-chlorophenyl)maleimide (0.2 mmol) and methyl glycinate hydrochloride (0.1 mmol) in toluene (10 ml) was heated under reflux overnight. The reaction mixture was cooled to ambient temperature and the resulting precipitate was collected by filtration and washed with hexane to obtain the pure heterocyclic product (yield 80%; m.p. 541–3 K). MS (EI, 70 eV) m/z (%): 963 (M+, 5), 756 (25), 525 (13), 273 (36), 233 (100), 207 (58), 77 (90). Crystals of the title solvate, (I), were grown by slow evaporation, at ambient temperature and in air, of a solution in ethanol–dimethylformamide (1:1 v/v).

Refinement top

All H atoms were located in difference maps and subsequently treated as riding atoms in geometrically idealized positions, with C—H = 0.95 (aromatic, formyl and pyrazole), 0.98 (methyl) or 1.00 Å (aliphatic CH), and with Uiso(H) = kUeq(C), where k = 1.5 for the methyl groups, which were permitted to rotate but not to tilt, and k = 1.2 for all other H atoms.

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The independent molecular components of (I), showing the atom-labelling scheme. For the sake of clarity, H atoms have been omitted. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A stereoview of part of the crystal structure of (I), showing the formation of a hydrogen-bonded chain of rings along [100]. For the sake of clarity, the dimethylformamide molecules and H atoms not involved in the motif shown have been omitted.
[Figure 3] Fig. 3. A stereoview of part of the crystal structure of (I), showing the formation of a hydrogen-bonded chain of rings along [010]. For the sake of clarity, the dimethylformamide molecules and the H atoms not involved in the motif shown have been omitted.
[Figure 4] Fig. 4. A stereoview of part of the crystal structure of (I), showing the formation of a hydrogen-bonded chain of rings along [111]. For the sake of clarity, the dimethylformamide molecules and the H atoms not involved in the motif shown have been omitted.
Methyl (3aRS,3cRS,6cSR,7RS,8RS,8aSR)- 2,5-bis(4-chlorophenyl)-7,9-bis(1,3-diphenyl-1H-pyrazol-4-yl)-1,3,4,6- tetraoxododecahydro-1H-dipyrrolo[3,4-a:3',4'- f]pyrrolizine-3b-carboxylate dimethylformamide disolvate top
Crystal data top
C55H39Cl2N7O6·2C3H7NOZ = 2
Mr = 1111.02F(000) = 1160
Triclinic, P1Dx = 1.370 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.948 (3) ÅCell parameters from 12351 reflections
b = 14.279 (3) Åθ = 2.5–27.5°
c = 16.3474 (16) ŵ = 0.19 mm1
α = 70.147 (12)°T = 120 K
β = 86.297 (13)°Prism, colourless
γ = 62.265 (16)°0.45 × 0.19 × 0.18 mm
V = 2693.4 (9) Å3
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
12351 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode8531 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.5°
ϕ and ω scansh = 1818
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1818
Tmin = 0.920, Tmax = 0.967l = 2121
67989 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0581P)2 + 1.125P]
where P = (Fo2 + 2Fc2)/3
12351 reflections(Δ/σ)max = 0.001
726 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C55H39Cl2N7O6·2C3H7NOγ = 62.265 (16)°
Mr = 1111.02V = 2693.4 (9) Å3
Triclinic, P1Z = 2
a = 13.948 (3) ÅMo Kα radiation
b = 14.279 (3) ŵ = 0.19 mm1
c = 16.3474 (16) ÅT = 120 K
α = 70.147 (12)°0.45 × 0.19 × 0.18 mm
β = 86.297 (13)°
Data collection top
Bruker Nonius KappaCCD area-detector
diffractometer
12351 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
8531 reflections with I > 2σ(I)
Tmin = 0.920, Tmax = 0.967Rint = 0.051
67989 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.125H-atom parameters constrained
S = 1.05Δρmax = 0.26 e Å3
12351 reflectionsΔρmin = 0.32 e Å3
726 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.59197 (14)0.43024 (15)0.75264 (12)0.0190 (4)
O10.54236 (10)0.39679 (11)0.72231 (8)0.0237 (3)
N20.60969 (12)0.40874 (12)0.84157 (10)0.0197 (3)
C30.65386 (14)0.47196 (15)0.85727 (12)0.0188 (4)
O30.67625 (10)0.46764 (11)0.92914 (8)0.0229 (3)
C3a0.66531 (14)0.54706 (15)0.76897 (11)0.0190 (4)
H3a0.60850.62760.75520.023*
C3b0.77993 (14)0.53746 (15)0.75821 (12)0.0190 (4)
C3c0.78734 (15)0.63688 (15)0.68061 (12)0.0207 (4)
H3c0.81480.67710.70420.025*
C40.68300 (15)0.72008 (15)0.62078 (12)0.0214 (4)
O40.60163 (11)0.79207 (11)0.63615 (9)0.0264 (3)
N50.69510 (12)0.70013 (12)0.54173 (10)0.0203 (3)
C60.80072 (15)0.61600 (15)0.53882 (12)0.0214 (4)
O60.82695 (11)0.58626 (11)0.47626 (8)0.0263 (3)
C6a0.86905 (15)0.57786 (15)0.62383 (12)0.0207 (4)
H6a0.92380.60620.61140.025*
C70.92677 (14)0.45137 (15)0.68358 (12)0.0196 (4)
H70.98000.44490.72600.024*
N7a0.84093 (12)0.43537 (12)0.73617 (9)0.0181 (3)
C80.76600 (14)0.41919 (15)0.68802 (11)0.0181 (4)
H80.77290.44650.62400.022*
C8a0.64809 (14)0.49793 (15)0.70454 (12)0.0186 (4)
H8a0.60350.55860.64900.022*
C210.57673 (15)0.33689 (15)0.90816 (12)0.0210 (4)
C220.61067 (15)0.22754 (16)0.91061 (13)0.0246 (4)
H220.65570.20050.86910.030*
C230.57798 (16)0.15831 (16)0.97460 (13)0.0276 (4)
H230.60060.08330.97740.033*
C240.51196 (16)0.20026 (16)1.03423 (12)0.0246 (4)
Cl240.46852 (4)0.11574 (4)1.11409 (3)0.03337 (13)
C250.47738 (16)0.30929 (17)1.03145 (12)0.0259 (4)
H250.43240.33641.07300.031*
C260.50936 (15)0.37827 (16)0.96713 (12)0.0233 (4)
H260.48510.45390.96350.028*
C310.83165 (15)0.52547 (15)0.84412 (12)0.0208 (4)
O310.90394 (11)0.44073 (11)0.89322 (8)0.0261 (3)
O320.78085 (11)0.62533 (11)0.85560 (8)0.0248 (3)
C320.82096 (19)0.6281 (2)0.93348 (15)0.0379 (5)
H32A0.80890.57650.98530.057*
H32B0.78210.70500.93460.057*
H32C0.89910.60450.93340.057*
C510.61161 (14)0.76378 (15)0.46882 (12)0.0211 (4)
C520.58316 (16)0.70722 (16)0.42880 (13)0.0247 (4)
H520.61810.62700.45020.030*
C530.50371 (16)0.76801 (16)0.35751 (13)0.0258 (4)
H530.48350.73010.32970.031*
C540.45438 (15)0.88471 (16)0.32758 (12)0.0246 (4)
Cl540.35482 (4)0.96110 (4)0.23794 (3)0.03206 (13)
C550.48141 (15)0.94247 (16)0.36696 (13)0.0241 (4)
H550.44631.02270.34540.029*
C560.56046 (15)0.88125 (16)0.43827 (12)0.0229 (4)
H560.57980.91940.46630.027*
N711.05304 (12)0.24859 (13)0.56853 (10)0.0222 (3)
N721.13209 (12)0.19709 (13)0.63693 (10)0.0233 (3)
C731.09425 (15)0.26395 (15)0.68484 (12)0.0219 (4)
C740.99132 (15)0.35961 (15)0.64693 (12)0.0214 (4)
C750.96899 (15)0.34560 (15)0.57256 (12)0.0221 (4)
H750.90590.39510.53130.027*
C7111.06570 (16)0.20263 (15)0.50128 (12)0.0232 (4)
C7120.97514 (17)0.22644 (17)0.45208 (13)0.0304 (5)
H7120.90410.26970.46520.036*
C7130.9886 (2)0.18683 (18)0.38333 (15)0.0392 (5)
H7130.92640.20430.34860.047*
C7141.0917 (2)0.12214 (18)0.36485 (14)0.0395 (6)
H7141.10050.09530.31760.047*
C7151.18193 (19)0.09673 (18)0.41548 (15)0.0364 (5)
H7151.25280.05170.40320.044*
C7161.17016 (17)0.13638 (17)0.48430 (14)0.0292 (4)
H7161.23240.11850.51910.035*
C7311.16154 (15)0.23431 (15)0.76469 (13)0.0232 (4)
C7321.27475 (16)0.18880 (16)0.76550 (14)0.0289 (4)
H7321.30810.17380.71570.035*
C7331.33828 (17)0.16553 (18)0.83826 (14)0.0329 (5)
H7331.41490.13580.83780.039*
C7341.29103 (18)0.18521 (18)0.91212 (15)0.0355 (5)
H7341.33510.16880.96220.043*
C7351.17929 (17)0.22895 (18)0.91238 (14)0.0324 (5)
H7351.14670.24230.96290.039*
C7361.11443 (16)0.25348 (16)0.83931 (13)0.0267 (4)
H7361.03780.28340.84010.032*
N810.88956 (12)0.11309 (12)0.79518 (10)0.0207 (3)
N820.84433 (12)0.11865 (13)0.72157 (10)0.0220 (3)
C830.79051 (14)0.22897 (15)0.67389 (12)0.0198 (4)
C840.80174 (14)0.29477 (15)0.71797 (11)0.0185 (4)
C850.86586 (15)0.21689 (15)0.79432 (12)0.0208 (4)
H850.88960.23270.83880.025*
C8110.96205 (16)0.00528 (16)0.85661 (12)0.0241 (4)
C8121.05119 (17)0.00673 (18)0.90020 (14)0.0336 (5)
H8121.06190.05670.89210.040*
C8131.1250 (2)0.1140 (2)0.95628 (15)0.0441 (6)
H8131.18650.12370.98680.053*
C8141.1094 (2)0.20603 (19)0.96779 (15)0.0433 (6)
H8141.16090.27901.00520.052*
C8151.01899 (18)0.19224 (17)0.92485 (14)0.0363 (5)
H8151.00770.25560.93380.044*
C8160.94458 (17)0.08626 (17)0.86877 (13)0.0298 (4)
H8160.88250.07660.83910.036*
C8310.73592 (15)0.26333 (15)0.58672 (12)0.0209 (4)
C8320.76015 (17)0.18195 (17)0.54855 (14)0.0314 (5)
H8320.81070.10530.57960.038*
C8330.71173 (18)0.21127 (19)0.46643 (14)0.0364 (5)
H8330.72810.15440.44220.044*
C8340.63980 (17)0.32241 (18)0.41910 (13)0.0310 (5)
H8340.60780.34240.36210.037*
C8350.61488 (16)0.40441 (17)0.45571 (12)0.0258 (4)
H8350.56570.48110.42370.031*
C8360.66158 (15)0.37476 (16)0.53902 (12)0.0230 (4)
H8360.64250.43140.56400.028*
C910.32649 (18)0.72970 (18)0.78748 (14)0.0337 (5)
H910.27400.70650.81170.040*
O910.42152 (12)0.65609 (13)0.80007 (10)0.0386 (4)
N910.28977 (14)0.83955 (15)0.74295 (11)0.0312 (4)
C920.36478 (19)0.8836 (2)0.70684 (16)0.0417 (6)
H92A0.37080.88800.64570.062*
H92B0.43670.83330.74080.062*
H92C0.33730.95920.70970.062*
C930.17302 (18)0.91999 (19)0.72402 (17)0.0433 (6)
H93A0.13150.88230.75620.065*
H93B0.15110.94760.66110.065*
H93C0.15850.98380.74210.065*
C941.09468 (18)0.55855 (19)0.80133 (15)0.0355 (5)
H941.09470.57040.85510.043*
O941.00634 (12)0.58666 (13)0.76586 (10)0.0391 (4)
N941.19134 (14)0.51277 (15)0.77202 (12)0.0350 (4)
C951.2004 (2)0.4879 (2)0.69203 (16)0.0439 (6)
H95A1.12750.51360.66530.066*
H95B1.24420.40630.70560.066*
H95C1.23570.52700.65120.066*
C961.29245 (19)0.4769 (2)0.82245 (18)0.0487 (6)
H96A1.27570.50070.87350.073*
H96B1.33410.51140.78580.073*
H96C1.33560.39440.84200.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0148 (8)0.0184 (9)0.0207 (9)0.0047 (7)0.0009 (7)0.0076 (7)
O10.0241 (7)0.0278 (7)0.0243 (7)0.0151 (6)0.0029 (5)0.0108 (6)
N20.0212 (8)0.0192 (8)0.0191 (8)0.0102 (6)0.0030 (6)0.0065 (6)
C30.0149 (8)0.0183 (9)0.0225 (9)0.0059 (7)0.0039 (7)0.0094 (7)
O30.0249 (7)0.0266 (7)0.0204 (7)0.0133 (6)0.0038 (5)0.0104 (6)
C3a0.0172 (9)0.0179 (9)0.0220 (9)0.0077 (7)0.0034 (7)0.0083 (7)
C3b0.0188 (9)0.0183 (9)0.0213 (9)0.0089 (7)0.0026 (7)0.0084 (7)
C3c0.0220 (9)0.0196 (9)0.0236 (9)0.0110 (8)0.0045 (7)0.0097 (8)
C40.0250 (10)0.0186 (9)0.0223 (9)0.0120 (8)0.0042 (8)0.0070 (8)
O40.0265 (7)0.0211 (7)0.0269 (7)0.0068 (6)0.0056 (6)0.0101 (6)
N50.0194 (8)0.0180 (8)0.0216 (8)0.0071 (6)0.0023 (6)0.0074 (6)
C60.0223 (9)0.0184 (9)0.0235 (10)0.0107 (8)0.0057 (8)0.0064 (8)
O60.0290 (7)0.0248 (7)0.0223 (7)0.0097 (6)0.0070 (6)0.0102 (6)
C6a0.0201 (9)0.0196 (9)0.0230 (9)0.0097 (8)0.0048 (7)0.0082 (8)
C70.0180 (9)0.0210 (9)0.0211 (9)0.0092 (7)0.0038 (7)0.0089 (7)
N7a0.0177 (7)0.0183 (8)0.0204 (8)0.0087 (6)0.0034 (6)0.0089 (6)
C80.0176 (9)0.0201 (9)0.0169 (9)0.0086 (7)0.0005 (7)0.0071 (7)
C8a0.0183 (9)0.0179 (9)0.0188 (9)0.0078 (7)0.0013 (7)0.0066 (7)
C210.0205 (9)0.0214 (9)0.0206 (9)0.0109 (8)0.0003 (7)0.0050 (8)
C220.0238 (10)0.0228 (10)0.0272 (10)0.0101 (8)0.0069 (8)0.0106 (8)
C230.0292 (11)0.0194 (10)0.0330 (11)0.0107 (8)0.0033 (9)0.0088 (8)
C240.0258 (10)0.0264 (10)0.0214 (9)0.0156 (8)0.0013 (8)0.0032 (8)
Cl240.0393 (3)0.0334 (3)0.0277 (3)0.0227 (2)0.0057 (2)0.0033 (2)
C250.0275 (10)0.0322 (11)0.0224 (10)0.0167 (9)0.0067 (8)0.0114 (8)
C260.0248 (10)0.0246 (10)0.0246 (10)0.0130 (8)0.0043 (8)0.0117 (8)
C310.0202 (9)0.0221 (10)0.0240 (10)0.0121 (8)0.0063 (8)0.0101 (8)
O310.0248 (7)0.0275 (7)0.0236 (7)0.0102 (6)0.0007 (6)0.0091 (6)
O320.0282 (7)0.0272 (7)0.0257 (7)0.0137 (6)0.0038 (6)0.0160 (6)
C320.0389 (13)0.0469 (14)0.0380 (12)0.0182 (11)0.0003 (10)0.0286 (11)
C510.0189 (9)0.0214 (9)0.0216 (9)0.0090 (8)0.0052 (7)0.0073 (8)
C520.0277 (10)0.0203 (9)0.0272 (10)0.0127 (8)0.0039 (8)0.0079 (8)
C530.0282 (10)0.0279 (10)0.0276 (10)0.0171 (9)0.0045 (8)0.0115 (8)
C540.0198 (9)0.0294 (11)0.0254 (10)0.0135 (8)0.0052 (8)0.0083 (8)
Cl540.0264 (3)0.0361 (3)0.0308 (3)0.0162 (2)0.0027 (2)0.0052 (2)
C550.0212 (9)0.0211 (9)0.0284 (10)0.0100 (8)0.0051 (8)0.0072 (8)
C560.0228 (9)0.0229 (10)0.0271 (10)0.0127 (8)0.0059 (8)0.0113 (8)
N710.0206 (8)0.0220 (8)0.0253 (8)0.0089 (7)0.0037 (6)0.0116 (7)
N720.0205 (8)0.0225 (8)0.0267 (8)0.0092 (7)0.0024 (7)0.0098 (7)
C730.0200 (9)0.0198 (9)0.0264 (10)0.0101 (8)0.0057 (8)0.0083 (8)
C740.0198 (9)0.0214 (9)0.0242 (10)0.0108 (8)0.0047 (7)0.0081 (8)
C750.0192 (9)0.0214 (9)0.0267 (10)0.0092 (8)0.0048 (8)0.0106 (8)
C7110.0297 (10)0.0204 (9)0.0234 (10)0.0140 (8)0.0070 (8)0.0095 (8)
C7120.0317 (11)0.0271 (11)0.0321 (11)0.0115 (9)0.0024 (9)0.0134 (9)
C7130.0493 (14)0.0316 (12)0.0348 (12)0.0139 (11)0.0030 (10)0.0157 (10)
C7140.0605 (16)0.0309 (12)0.0295 (11)0.0193 (11)0.0103 (11)0.0177 (10)
C7150.0433 (13)0.0296 (12)0.0421 (13)0.0185 (10)0.0213 (11)0.0204 (10)
C7160.0309 (11)0.0250 (10)0.0369 (11)0.0157 (9)0.0112 (9)0.0147 (9)
C7310.0213 (9)0.0180 (9)0.0285 (10)0.0076 (8)0.0004 (8)0.0080 (8)
C7320.0223 (10)0.0261 (11)0.0345 (11)0.0065 (8)0.0030 (8)0.0135 (9)
C7330.0206 (10)0.0320 (11)0.0407 (12)0.0067 (9)0.0016 (9)0.0141 (10)
C7340.0310 (11)0.0364 (12)0.0358 (12)0.0117 (10)0.0064 (9)0.0133 (10)
C7350.0341 (12)0.0372 (12)0.0289 (11)0.0173 (10)0.0043 (9)0.0146 (9)
C7360.0246 (10)0.0265 (10)0.0306 (11)0.0121 (8)0.0041 (8)0.0118 (9)
N810.0212 (8)0.0169 (8)0.0201 (8)0.0066 (6)0.0013 (6)0.0049 (6)
N820.0234 (8)0.0212 (8)0.0212 (8)0.0102 (7)0.0004 (6)0.0072 (7)
C830.0192 (9)0.0198 (9)0.0200 (9)0.0092 (8)0.0018 (7)0.0067 (7)
C840.0169 (9)0.0207 (9)0.0188 (9)0.0090 (7)0.0035 (7)0.0079 (7)
C850.0214 (9)0.0202 (9)0.0220 (9)0.0103 (8)0.0025 (7)0.0083 (8)
C8110.0257 (10)0.0211 (10)0.0191 (9)0.0069 (8)0.0027 (8)0.0059 (8)
C8120.0356 (12)0.0282 (11)0.0306 (11)0.0101 (9)0.0065 (9)0.0084 (9)
C8130.0405 (13)0.0389 (13)0.0350 (13)0.0063 (11)0.0147 (10)0.0072 (10)
C8140.0465 (14)0.0266 (12)0.0307 (12)0.0021 (10)0.0035 (11)0.0008 (9)
C8150.0379 (12)0.0204 (10)0.0356 (12)0.0078 (9)0.0087 (10)0.0021 (9)
C8160.0290 (11)0.0240 (10)0.0317 (11)0.0104 (9)0.0062 (9)0.0082 (9)
C8310.0201 (9)0.0212 (9)0.0232 (9)0.0103 (8)0.0024 (7)0.0088 (8)
C8320.0356 (12)0.0248 (10)0.0310 (11)0.0093 (9)0.0040 (9)0.0125 (9)
C8330.0412 (13)0.0341 (12)0.0356 (12)0.0122 (10)0.0030 (10)0.0212 (10)
C8340.0288 (11)0.0409 (12)0.0245 (10)0.0150 (10)0.0003 (8)0.0144 (9)
C8350.0239 (10)0.0269 (10)0.0236 (10)0.0109 (8)0.0016 (8)0.0070 (8)
C8360.0229 (10)0.0253 (10)0.0232 (10)0.0117 (8)0.0026 (8)0.0108 (8)
C910.0326 (12)0.0335 (12)0.0368 (12)0.0154 (10)0.0087 (9)0.0155 (10)
O910.0297 (8)0.0346 (8)0.0430 (9)0.0082 (7)0.0016 (7)0.0138 (7)
N910.0280 (9)0.0304 (10)0.0355 (10)0.0128 (8)0.0095 (8)0.0145 (8)
C920.0385 (13)0.0436 (14)0.0476 (14)0.0251 (11)0.0063 (11)0.0135 (11)
C930.0343 (13)0.0331 (13)0.0558 (15)0.0113 (10)0.0147 (11)0.0161 (11)
C940.0333 (12)0.0400 (13)0.0372 (12)0.0214 (10)0.0050 (10)0.0126 (10)
O940.0274 (8)0.0422 (9)0.0486 (10)0.0190 (7)0.0014 (7)0.0127 (8)
N940.0254 (9)0.0346 (10)0.0424 (11)0.0154 (8)0.0027 (8)0.0087 (8)
C950.0448 (14)0.0390 (13)0.0493 (15)0.0207 (11)0.0137 (11)0.0174 (11)
C960.0302 (12)0.0464 (15)0.0652 (17)0.0196 (11)0.0051 (12)0.0105 (13)
Geometric parameters (Å, º) top
C1—O11.210 (2)C712—H7120.9500
C1—N21.393 (2)C713—C7141.382 (3)
C1—C8a1.508 (3)C713—H7130.9500
N2—C31.399 (2)C714—C7151.380 (3)
N2—C211.437 (2)C714—H7140.9500
C3—O31.209 (2)C715—C7161.391 (3)
C3—C3a1.529 (3)C715—H7150.9500
C3a—C8a1.533 (2)C716—H7160.9500
C3a—C3b1.543 (2)C731—C7361.397 (3)
C3a—H3a1.0000C731—C7321.399 (3)
C3b—N7a1.463 (2)C732—C7331.380 (3)
C3b—C311.541 (2)C732—H7320.9500
C3b—C3c1.591 (3)C733—C7341.388 (3)
C3c—C41.507 (3)C733—H7330.9500
C3c—C6a1.540 (3)C734—C7351.383 (3)
C3c—H3c1.0000C734—H7340.9500
C4—O41.209 (2)C735—C7361.389 (3)
C4—N51.399 (2)C735—H7350.9500
N5—C61.414 (2)C736—H7360.9500
N5—C511.436 (2)N81—C851.355 (2)
C6—O61.209 (2)N81—N821.356 (2)
C6—C6a1.520 (3)N81—C8111.426 (2)
C6a—C71.554 (3)N82—C831.339 (2)
C6a—H6a1.0000C83—C841.428 (2)
C7—N7a1.488 (2)C83—C8311.473 (2)
C7—C741.501 (3)C84—C851.367 (3)
C7—H71.0000C85—H850.9500
N7a—C81.490 (2)C811—C8121.384 (3)
C8—C841.504 (2)C811—C8161.386 (3)
C8—C8a1.572 (2)C812—C8131.395 (3)
C8—H81.0000C812—H8120.9500
C8a—H8a1.0000C813—C8141.379 (4)
C21—C261.384 (3)C813—H8130.9500
C21—C221.391 (3)C814—C8151.383 (3)
C22—C231.391 (3)C814—H8140.9500
C22—H220.9500C815—C8161.388 (3)
C23—C241.387 (3)C815—H8150.9500
C23—H230.9500C816—H8160.9500
C24—C251.384 (3)C831—C8361.393 (3)
C24—Cl241.742 (2)C831—C8321.398 (3)
C25—C261.385 (3)C832—C8331.381 (3)
C25—H250.9500C832—H8320.9500
C26—H260.9500C833—C8341.381 (3)
C31—O311.198 (2)C833—H8330.9500
C31—O321.340 (2)C834—C8351.386 (3)
O32—C321.443 (2)C834—H8340.9500
C32—H32A0.9800C835—C8361.387 (3)
C32—H32B0.9800C835—H8350.9500
C32—H32C0.9800C836—H8360.9500
C51—C521.389 (3)C91—O911.223 (3)
C51—C561.391 (3)C91—N911.333 (3)
C52—C531.387 (3)C91—H910.9500
C52—H520.9500N91—C921.456 (3)
C53—C541.383 (3)N91—C931.466 (3)
C53—H530.9500C92—H92A0.9800
C54—C551.385 (3)C92—H92B0.9800
C54—Cl541.742 (2)C92—H92C0.9800
C55—C561.384 (3)C93—H93A0.9800
C55—H550.9500C93—H93B0.9800
C56—H560.9500C93—H93C0.9800
N71—C751.356 (2)C94—O941.220 (2)
N71—N721.361 (2)C94—N941.336 (3)
N71—C7111.424 (2)C94—H940.9500
N72—C731.338 (2)N94—C951.451 (3)
C73—C741.423 (3)N94—C961.457 (3)
C73—C7311.475 (3)C95—H95A0.9800
C74—C751.374 (3)C95—H95B0.9800
C75—H750.9500C95—H95C0.9800
C711—C7121.380 (3)C96—H96A0.9800
C711—C7161.392 (3)C96—H96B0.9800
C712—C7131.387 (3)C96—H96C0.9800
O1—C1—N2124.61 (17)C712—C711—C716120.63 (18)
O1—C1—C8a128.00 (16)C712—C711—N71120.08 (17)
N2—C1—C8a107.36 (14)C716—C711—N71119.26 (17)
C1—N2—C3112.48 (15)C711—C712—C713119.5 (2)
C1—N2—C21122.84 (14)C711—C712—H712120.2
C3—N2—C21124.47 (15)C713—C712—H712120.2
O3—C3—N2124.53 (17)C714—C713—C712120.6 (2)
O3—C3—C3a127.29 (16)C714—C713—H713119.7
N2—C3—C3a108.17 (14)C712—C713—H713119.7
C3—C3a—C8a103.06 (14)C715—C714—C713119.6 (2)
C3—C3a—C3b115.13 (14)C715—C714—H714120.2
C8a—C3a—C3b105.30 (14)C713—C714—H714120.2
C3—C3a—H3a111.0C714—C715—C716120.7 (2)
C8a—C3a—H3a111.0C714—C715—H715119.6
C3b—C3a—H3a111.0C716—C715—H715119.6
N7a—C3b—C31111.15 (14)C715—C716—C711118.9 (2)
N7a—C3b—C3a103.87 (14)C715—C716—H716120.5
C31—C3b—C3a110.64 (14)C711—C716—H716120.5
N7a—C3b—C3c106.21 (14)C736—C731—C732118.87 (18)
C31—C3b—C3c108.57 (14)C736—C731—C73121.38 (17)
C3a—C3b—C3c116.24 (14)C732—C731—C73119.72 (18)
C4—C3c—C6a105.76 (15)C733—C732—C731120.40 (19)
C4—C3c—C3b114.70 (15)C733—C732—H732119.8
C6a—C3c—C3b104.83 (14)C731—C732—H732119.8
C4—C3c—H3c110.4C732—C733—C734120.51 (19)
C6a—C3c—H3c110.4C732—C733—H733119.7
C3b—C3c—H3c110.4C734—C733—H733119.7
O4—C4—N5124.44 (17)C735—C734—C733119.55 (19)
O4—C4—C3c127.60 (17)C735—C734—H734120.2
N5—C4—C3c107.97 (15)C733—C734—H734120.2
C4—N5—C6112.95 (15)C734—C735—C736120.5 (2)
C4—N5—C51123.59 (15)C734—C735—H735119.8
C6—N5—C51123.33 (15)C736—C735—H735119.8
O6—C6—N5122.87 (17)C735—C736—C731120.20 (19)
O6—C6—C6a129.29 (17)C735—C736—H736119.9
N5—C6—C6a107.81 (15)C731—C736—H736119.9
C6—C6a—C3c104.55 (14)C85—N81—N82111.85 (14)
C6—C6a—C7120.60 (15)C85—N81—C811128.59 (15)
C3c—C6a—C7103.85 (14)N82—N81—C811119.17 (14)
C6—C6a—H6a109.1C83—N82—N81105.05 (14)
C3c—C6a—H6a109.1N82—C83—C84110.88 (15)
C7—C6a—H6a109.1N82—C83—C831118.49 (16)
N7a—C7—C74113.75 (14)C84—C83—C831130.55 (16)
N7a—C7—C6a104.41 (14)C85—C84—C83104.38 (16)
C74—C7—C6a121.47 (15)C85—C84—C8124.54 (15)
N7a—C7—H7105.3C83—C84—C8130.71 (16)
C74—C7—H7105.3N81—C85—C84107.83 (16)
C6a—C7—H7105.3N81—C85—H85126.1
C3b—N7a—C7105.90 (13)C84—C85—H85126.1
C3b—N7a—C8110.06 (13)C812—C811—C816121.31 (18)
C7—N7a—C8112.94 (13)C812—C811—N81119.15 (18)
N7a—C8—C84108.01 (13)C816—C811—N81119.48 (17)
N7a—C8—C8a105.36 (13)C811—C812—C813118.6 (2)
C84—C8—C8a117.30 (15)C811—C812—H812120.7
N7a—C8—H8108.6C813—C812—H812120.7
C84—C8—H8108.6C814—C813—C812120.6 (2)
C8a—C8—H8108.6C814—C813—H813119.7
C1—C8a—C3a105.06 (14)C812—C813—H813119.7
C1—C8a—C8111.22 (14)C813—C814—C815120.0 (2)
C3a—C8a—C8105.06 (14)C813—C814—H814120.0
C1—C8a—H8a111.7C815—C814—H814120.0
C3a—C8a—H8a111.7C814—C815—C816120.2 (2)
C8—C8a—H8a111.7C814—C815—H815119.9
C26—C21—C22121.01 (18)C816—C815—H815119.9
C26—C21—N2119.72 (16)C811—C816—C815119.2 (2)
C22—C21—N2119.25 (17)C811—C816—H816120.4
C23—C22—C21119.26 (18)C815—C816—H816120.4
C23—C22—H22120.4C836—C831—C832117.74 (17)
C21—C22—H22120.4C836—C831—C83122.90 (16)
C24—C23—C22119.10 (18)C832—C831—C83119.34 (17)
C24—C23—H23120.4C833—C832—C831120.97 (19)
C22—C23—H23120.4C833—C832—H832119.5
C25—C24—C23121.72 (18)C831—C832—H832119.5
C25—C24—Cl24118.34 (15)C832—C833—C834120.70 (19)
C23—C24—Cl24119.94 (15)C832—C833—H833119.6
C24—C25—C26118.98 (18)C834—C833—H833119.6
C24—C25—H25120.5C833—C834—C835119.20 (18)
C26—C25—H25120.5C833—C834—H834120.4
C21—C26—C25119.91 (18)C835—C834—H834120.4
C21—C26—H26120.0C834—C835—C836120.18 (18)
C25—C26—H26120.0C834—C835—H835119.9
O31—C31—O32125.60 (17)C836—C835—H835119.9
O31—C31—C3b125.83 (16)C835—C836—C831121.17 (18)
O32—C31—C3b108.56 (15)C835—C836—H836119.4
C31—O32—C32115.24 (15)C831—C836—H836119.4
O32—C32—H32A109.5O91—C91—N91126.0 (2)
O32—C32—H32B109.5O91—C91—H91117.0
H32A—C32—H32B109.5N91—C91—H91117.0
O32—C32—H32C109.5C91—N91—C92120.84 (19)
H32A—C32—H32C109.5C91—N91—C93122.02 (19)
H32B—C32—H32C109.5C92—N91—C93117.06 (18)
C52—C51—C56120.46 (17)N91—C92—H92A109.5
C52—C51—N5119.52 (16)N91—C92—H92B109.5
C56—C51—N5120.02 (16)H92A—C92—H92B109.5
C53—C52—C51119.93 (17)N91—C92—H92C109.5
C53—C52—H52120.0H92A—C92—H92C109.5
C51—C52—H52120.0H92B—C92—H92C109.5
C54—C53—C52118.82 (17)N91—C93—H93A109.5
C54—C53—H53120.6N91—C93—H93B109.5
C52—C53—H53120.6H93A—C93—H93B109.5
C53—C54—C55122.00 (18)N91—C93—H93C109.5
C53—C54—Cl54118.86 (15)H93A—C93—H93C109.5
C55—C54—Cl54119.14 (15)H93B—C93—H93C109.5
C56—C55—C54118.84 (18)O94—C94—N94126.4 (2)
C56—C55—H55120.6O94—C94—H94116.8
C54—C55—H55120.6N94—C94—H94116.8
C55—C56—C51119.94 (17)C94—N94—C95121.03 (19)
C55—C56—H56120.0C94—N94—C96121.6 (2)
C51—C56—H56120.0C95—N94—C96117.2 (2)
C75—N71—N72112.16 (14)N94—C95—H95A109.5
C75—N71—C711127.10 (16)N94—C95—H95B109.5
N72—N71—C711120.69 (15)H95A—C95—H95B109.5
C73—N72—N71104.20 (14)N94—C95—H95C109.5
N72—C73—C74112.02 (16)H95A—C95—H95C109.5
N72—C73—C731119.02 (16)H95B—C95—H95C109.5
C74—C73—C731128.92 (17)N94—C96—H96A109.5
C75—C74—C73103.80 (16)N94—C96—H96B109.5
C75—C74—C7130.51 (17)H96A—C96—H96B109.5
C73—C74—C7125.68 (16)N94—C96—H96C109.5
N71—C75—C74107.80 (16)H96A—C96—H96C109.5
N71—C75—H75126.1H96B—C96—H96C109.5
C74—C75—H75126.1
O1—C1—N2—C3170.43 (17)C3a—C3b—C31—O31106.4 (2)
C8a—C1—N2—C311.21 (19)C3c—C3b—C31—O31124.89 (19)
O1—C1—N2—C214.4 (3)C3a—C3b—C31—O3272.43 (18)
C8a—C1—N2—C21173.92 (15)C3c—C3b—C31—O3256.23 (18)
C1—N2—C3—O3179.97 (17)O31—C31—O32—C321.6 (3)
C21—N2—C3—O35.3 (3)C3b—C31—O32—C32179.49 (16)
C1—N2—C3—C3a1.36 (19)C4—N5—C51—C52130.36 (19)
C21—N2—C3—C3a173.41 (15)C4—N5—C51—C5650.2 (2)
O3—C3—C3a—C8a168.50 (17)C6—N5—C51—C56125.28 (19)
N2—C3—C3a—C8a12.88 (18)C56—C51—C52—C530.4 (3)
O3—C3—C3a—C3b54.4 (2)N5—C51—C52—C53179.05 (17)
N2—C3—C3a—C3b126.96 (15)C51—C52—C53—C540.1 (3)
C3—C3a—C3b—N7a80.68 (17)C52—C53—C54—C550.4 (3)
C8a—C3a—C3b—N7a32.09 (17)C52—C53—C54—Cl54179.87 (15)
C3—C3a—C3b—C3138.7 (2)C53—C54—C55—C560.2 (3)
C8a—C3a—C3b—C31151.45 (14)Cl54—C54—C55—C56179.88 (14)
C3—C3a—C3b—C3c163.07 (14)C54—C55—C56—C510.4 (3)
C8a—C3a—C3b—C3c84.16 (17)C52—C51—C56—C550.7 (3)
N7a—C3b—C3c—C4107.66 (16)N5—C51—C56—C55178.80 (17)
C31—C3b—C3c—C4132.74 (16)C75—N71—N72—C730.9 (2)
C3a—C3b—C3c—C47.3 (2)C711—N71—N72—C73178.54 (16)
N7a—C3b—C3c—C6a7.88 (17)N71—N72—C73—C740.8 (2)
C31—C3b—C3c—C6a111.73 (16)N71—N72—C73—C731178.76 (16)
C3a—C3b—C3c—C6a122.82 (16)N72—C73—C74—C750.4 (2)
C6a—C3c—C4—O4171.56 (18)C731—C73—C74—C75178.09 (19)
C3b—C3c—C4—O473.4 (2)N72—C73—C74—C7179.63 (17)
C6a—C3c—C4—N58.67 (19)C731—C73—C74—C71.9 (3)
C3b—C3c—C4—N5106.33 (17)N7a—C7—C74—C7583.3 (2)
O4—C4—N5—C6176.14 (17)C6a—C7—C74—C7542.7 (3)
C3c—C4—N5—C64.1 (2)C6a—C7—C74—C73137.29 (19)
O4—C4—N5—C510.3 (3)N72—N71—C75—C740.7 (2)
C3c—C4—N5—C51179.96 (15)C711—N71—C75—C74178.16 (17)
C4—N5—C6—O6179.48 (17)C73—C74—C75—N710.2 (2)
C51—N5—C6—O64.6 (3)C7—C74—C75—N71179.79 (18)
C4—N5—C6—C6a2.4 (2)C75—N71—C711—C71227.1 (3)
C51—N5—C6—C6a173.50 (15)C75—N71—C711—C716151.08 (19)
O6—C6—C6a—C3c174.45 (19)N72—N71—C711—C71626.2 (3)
N5—C6—C6a—C3c7.59 (19)C716—C711—C712—C7132.0 (3)
O6—C6—C6a—C758.3 (3)N71—C711—C712—C713176.11 (18)
N5—C6—C6a—C7123.76 (17)C711—C712—C713—C7141.2 (3)
C4—C3c—C6a—C69.73 (18)C712—C713—C714—C7150.1 (3)
C3b—C3c—C6a—C6111.86 (15)C713—C714—C715—C7160.6 (3)
C4—C3c—C6a—C7137.01 (14)C714—C715—C716—C7110.2 (3)
C3b—C3c—C6a—C715.42 (17)C712—C711—C716—C7151.5 (3)
C6—C6a—C7—N7a83.06 (19)N71—C711—C716—C715176.63 (18)
C3c—C6a—C7—N7a33.46 (17)N72—C73—C731—C736143.85 (19)
C6—C6a—C7—C7447.1 (2)C74—C73—C731—C73638.6 (3)
C3c—C6a—C7—C74163.61 (16)C74—C73—C731—C732139.7 (2)
C31—C3b—N7a—C788.53 (17)C736—C731—C732—C7331.3 (3)
C3a—C3b—N7a—C7152.47 (13)C73—C731—C732—C733176.99 (18)
C3c—C3b—N7a—C729.37 (16)C731—C732—C733—C7341.0 (3)
C31—C3b—N7a—C8149.10 (14)C732—C733—C734—C7350.3 (3)
C3a—C3b—N7a—C830.10 (18)C733—C734—C735—C7360.2 (3)
C3c—C3b—N7a—C893.00 (16)C734—C735—C736—C7310.1 (3)
C74—C7—N7a—C3b174.18 (14)C732—C731—C736—C7350.8 (3)
C6a—C7—N7a—C3b39.60 (16)C73—C731—C736—C735177.43 (18)
C74—C7—N7a—C853.66 (19)C85—N81—N82—C830.4 (2)
C6a—C7—N7a—C880.92 (16)C811—N81—N82—C83173.86 (16)
C3b—N7a—C8—C84142.18 (15)N81—N82—C83—C840.0 (2)
C7—N7a—C8—C8499.71 (16)N81—N82—C83—C831177.14 (16)
C3b—N7a—C8—C8a16.06 (18)N82—C83—C84—C850.3 (2)
C7—N7a—C8—C8a134.17 (14)C831—C83—C84—C85176.35 (19)
O1—C1—C8a—C3a162.85 (17)N82—C83—C84—C8173.48 (17)
N2—C1—C8a—C3a18.86 (18)C831—C83—C84—C83.2 (3)
O1—C1—C8a—C884.0 (2)N7a—C8—C84—C8519.7 (2)
N2—C1—C8a—C894.28 (16)C8a—C8—C84—C8599.1 (2)
C3—C3a—C8a—C118.78 (17)C8a—C8—C84—C8389.0 (2)
C3b—C3a—C8a—C1139.81 (14)N82—N81—C85—C840.6 (2)
C3—C3a—C8a—C898.64 (15)C811—N81—C85—C84173.32 (17)
C3b—C3a—C8a—C822.39 (18)C83—C84—C85—N810.5 (2)
N7a—C8—C8a—C1117.90 (15)C8—C84—C85—N81174.23 (16)
C84—C8—C8a—C12.3 (2)C85—N81—C811—C81228.8 (3)
N7a—C8—C8a—C3a4.75 (17)C85—N81—C811—C816153.89 (19)
C84—C8—C8a—C3a115.42 (16)N82—N81—C811—C81633.8 (3)
C1—N2—C21—C26124.16 (19)C816—C811—C812—C8130.9 (3)
C3—N2—C21—C2650.1 (2)N81—C811—C812—C813176.3 (2)
C1—N2—C21—C2254.0 (2)C811—C812—C813—C8140.2 (4)
N7a—C8—C84—C83152.27 (18)C812—C813—C814—C8151.2 (4)
N82—N81—C811—C812143.45 (18)C813—C814—C815—C8161.2 (4)
N82—C83—C831—C83213.5 (3)C812—C811—C816—C8151.0 (3)
N7a—C3b—C31—O318.4 (3)N81—C811—C816—C815176.28 (18)
C6—N5—C51—C5254.2 (2)C814—C815—C816—C8110.1 (3)
N7a—C7—C74—C7396.7 (2)N82—C83—C831—C836167.62 (18)
N72—N71—C711—C712155.67 (18)C84—C83—C831—C83615.9 (3)
N72—C73—C731—C73237.9 (3)C84—C83—C831—C832163.0 (2)
N7a—C3b—C31—O32172.70 (14)C836—C831—C832—C8330.1 (3)
C3—N2—C21—C22131.79 (18)C83—C831—C832—C833179.1 (2)
C26—C21—C22—C231.3 (3)C831—C832—C833—C8341.4 (4)
N2—C21—C22—C23179.44 (16)C832—C833—C834—C8351.3 (3)
C21—C22—C23—C240.2 (3)C833—C834—C835—C8360.2 (3)
C22—C23—C24—C250.3 (3)C834—C835—C836—C8311.5 (3)
C22—C23—C24—Cl24179.17 (14)C832—C831—C836—C8351.3 (3)
C23—C24—C25—C260.2 (3)C83—C831—C836—C835177.59 (18)
Cl24—C24—C25—C26178.62 (14)O91—C91—N91—C922.7 (3)
C22—C21—C26—C251.9 (3)O91—C91—N91—C93173.9 (2)
N2—C21—C26—C25179.99 (16)O94—C94—N94—C952.0 (4)
C24—C25—C26—C211.4 (3)O94—C94—N94—C96176.6 (2)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C51-C56 ring.
D—H···AD—HH···AD···AD—H···A
C3a—H3a···O911.002.543.104 (3)115
C3c—H3c···O941.002.463.102 (3)121
C7—H7···O941.002.513.275 (3)134
C53—H53···O1i0.952.413.355 (3)170
C55—H55···O4ii0.952.533.392 (3)151
C814—H814···O3iii0.952.493.422 (3)164
C835—H835···O1i0.952.493.280 (3)141
C732—H732···Cgiv0.952.813.654 (3)149
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+2, z+1; (iii) x+2, y, z+2; (iv) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC55H39Cl2N7O6·2C3H7NO
Mr1111.02
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)13.948 (3), 14.279 (3), 16.3474 (16)
α, β, γ (°)70.147 (12), 86.297 (13), 62.265 (16)
V3)2693.4 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.45 × 0.19 × 0.18
Data collection
DiffractometerBruker Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.920, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections
67989, 12351, 8531
Rint0.051
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.125, 1.05
No. of reflections12351
No. of parameters726
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.32

Computer programs: COLLECT (Nonius, 1999), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected torsion angles (º) top
C1—N2—C21—C2254.0 (2)C6—N5—C51—C5254.2 (2)
N7a—C8—C84—C83152.27 (18)N7a—C7—C74—C7396.7 (2)
N82—N81—C811—C812143.45 (18)N72—N71—C711—C712155.67 (18)
N82—C83—C831—C83213.5 (3)N72—C73—C731—C73237.9 (3)
N7a—C3b—C31—O318.4 (3)N7a—C3b—C31—O32172.70 (14)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C51-C56 ring.
D—H···AD—HH···AD···AD—H···A
C3a—H3a···O911.002.543.104 (3)115
C3c—H3c···O941.002.463.102 (3)121
C7—H7···O941.002.513.275 (3)134
C53—H53···O1i0.952.413.355 (3)170
C55—H55···O4ii0.952.533.392 (3)151
C814—H814···O3iii0.952.493.422 (3)164
C835—H835···O1i0.952.493.280 (3)141
C732—H732···Cgiv0.952.813.654 (3)149
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+2, z+1; (iii) x+2, y, z+2; (iv) x+2, y+1, z+1.
Ring-puckering parameters (Å, °) for the fused five-membered rings top
RingQ2ϕ2
N2/C1/C8a/C3a/C30.193 (2)257.2 (6)
N5/C4/C3c/C6/C60.096 (2)95.9 (13)
N7a/C3b/C3a/C8a/C80.311 (2)225.2 (4)
N7a/C3b/C3c/C6a/C70.368 (2)155.0 (3)
 

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