1′-Methylcyclooctane-1-spiro-3′-pyrrolidine-2′-spiro-3′′-indoline-2,2′′-dione and 1,1′-dimethylpiper­idine-3-spiro-3′-pyrrolidine-2′-spiro-3′′-indoline-2′′,4-dione

In both title compounds, C₁₉H₂₄N₂O₂, (I), and C₁₇H₂₁N₃O₂, (II), respectively, there are two mol­ecules in the asymmetric unit and the pyrrolidine rings adopt envelope conformations. The conformations of the cyclo­octane [in (I)] and 1-methyl­piperidone [in (II)] rings are boat–chair and chair, respectively. The indolin-2-one group is almost perpendicular to the pyrrolidine ring. Inter­molecular C—H...O, N—H...O and N—H...N inter­actions provide stability to the structures.

S1. Comment

Pharmacologically active compounds and many alkaloids have a substituted pyrrolidine sub-structure. 1,3-Dipolar cycloaddition of azomethine ylides with diverse dipolarophiles represents one of the most versatile approaches for the construction of highly functionalized five-membered ring heterocycles (Padwa, 1984). The spiro ring systems are of great interest as they exhibit a wide range of biological activities (Kobayashi et al., 1991; James et al., 1991). Spiropyrrolidines have attracted much attention as potential antileukaemic and anticonvulsant agents (Abou Gharbia et al., 1979), with antiviral (Lundahl et al., 1972) and local anaesthetic (Kornett & Thio, 1976) activities. Isatin and its derivatives have interesting biological activities and hence are widely used as precursors of many natural products (Saxton, 1983; Cui et al., 1996; Xue et al., 2000). Spiropyrrolidinyloxindole ring systems are also found in a number of alkaloids of biological importance (Hilton et al., 2000). Our interest in preparing pharmacologically active pyrrolidines led us to the title compounds, (I) and (II), and we have undertaken X-ray crystal structure determinations of (I) and (II) in order to establish their conformations.

The asymmetric units of compounds (I) and (II) contain two independent molecules; each pair has almost identical geometry (Figs. 1 and 2). In both (I) and (II), the bond lengths and angles show normal values and agree with each other (Allen et al., 1987), except for the bonds at the spiro junctions. The sums of the angles at N11 and N21 of the pyrrolidine rings [340.4 (2) and 341.5 (2)°, respectively, in compound (I), and 336.8 (2) and 336.1 (3)°, respectively, in compound (II)] are in accordance with sp³-hybridization (Beddoes et al., 1986; Kumar et al., 2006; Jeyabharathi et al., 2001), and the sums of the angles at N12 and N22 of the oxindole moiety [359.6 (2) and 359.9 (2)°, respectively, in compound (I), and 360 (2) and 360 (3)°, respectively, in compound (II)] are in accordance with sp² -hybridization (Govind et al., 2004; Kumar et al., 2006; Jeyabharathi et al., 2001). In compounds (I) and (II), the bond lengths within the oxindole moiety match those in similar structures (Kumar et al., 2006; Jeyabharathi et al., 2001), but the C—C and C—N bonds within the pyrrolidine ring are shorter (Table 6). The mean value of the Csp³—Csp³ bond lengths in the cyclooctane, (I) [1.528 (3) Å], is comparable with those in compounds with similar configurations [1.533 (2) Å (Latvala et al., 1993), 1.523 (5) Å (Hesse et al., 1993) and 1.525 (5) Å (Jacobsen et al., 2002)].

In compounds (I) and (II), the five-membered rings of the pyrrolidine moiety have envelope conformations with flap atoms C5 and C25 in (I), and N11 and N21 in (II). Puckering parameters (q₂ and ϕ₂; Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Δ; Nardelli, 1983) are shown in Table 5. The dihedral angles formed by the mean planes C4/C14/C18/C19 with C20/C19/C4 and C14/C15/C17/C18 with C15/C16/C17 in the cyclooctane substituted at C4 are 55.29 (2) and 57.59 (4)°, respectively; similar values are observed for the cyclooctane substituted at C24. These values are different from those in similar structures [60.09 (2) and 49.22 (4)°, respectively; Kumar et al., 2006]. The chair conformation of the 1-methylpiperidone ring in compound (II) is evident from the torsion angles (Table 3).

In the oxindole moieties, the phenyl and pyrrole rings are individually planar and make dihedral angles of 6.2 (2) and 6.7 (1)° in compound (I) and 4.2 (1) and 1.2 (1)° in compound (II), respectively, while atoms O11 and O21 deviate from the pyrrole ring of the oxindole moiety by -0.145 (4) and -0.192 (4) Å, respectively, in compound (I), and by -0.220 (4) and -0.232 (4) Å, respectively, in compound (II), because of the different interactions in which these O atoms are involved (Tables 2 and 4). The oxindole moieties are in a nearly perpendicular configuration with the respective pyrrolidine rings, as seen from the dihedral angles [81.7 (1) and 80.7 (1)° in compound (I), and 87.3 (1) and 89.1 (1)° in compound (II)]. In both compounds, in the benzene ring of the indole system, the endocyclic angles at C7, C11, C27 and C31 are contracted, while those at C10, C12, C30 and C32 are expanded (Tables 1 and 3). This may be due to the effect of the fusion of the smaller pyrrole ring to the six-membered benzene ring, with the strain taken up by angular distortion rather than by bond-length distortions (Seshadri et al., 2003). Compounds (I) and (II) are in centrosymmetric space groups, so there must be equal numbers of opposite enantiomers; they contain chiral atoms C4, C5, C24 and C25. Of the four possible stereoisomers, those present in compound (I) are S,S and its enantiomer R,R, and in compound (II) S,R and its enantiomer R,S.

The structure of (I) is stabilized by C—H···O and N—H···O interactions. The C11—H11···O11 and N12—H12···O21 interactions (Table 2) generate primary graph-set motifs (Etter et al., 1990) of C₁¹(6) and C₂²(8) and form a zigzag linear double chain parallel to the c axis (Fig. 3). These two interactions, along with an intermolecular N22—H22···O11 interaction, generate a secondary graph-set motif R₃²(10). In addition to this, a weaker intermolecular C29—H29···O22 (Table 2) interaction generates a graph-set motif C₁¹(8).

In compound (II), the intermolecular N22—H22···O11 and N22—H22···N11 (Table 4 and Fig. 4) bifurcated interactions together generate a graph-set motif R₁²(5). This, along with some weak interactions, pack the molecules to form a linear chain running along the a axis. Adjacent chains are only interconnected by means of van der Waals interactions.

Related literature

For related literature, see: Abou & Doukas (1979); Allen et al. (1987); Beddoes et al. (1986); Cremer & Pople (1975); Cui et al. (1996); Etter et al. (1990); Govind et al. (2004); Hesse et al. (1993); Hilton et al. (2000); Jacobsen et al. (2002); James et al. (1991); Jeyabharathi et al. (2001); Kobayashi et al. (1991); Kornett & Thio (1976); Kumar et al. (2006); Latvala et al. (1993); Lundahl et al. (1972); Nardelli (1983); Padwa (1984); Saxton (1983); Seshadri et al. (2003); Xue et al. (2000).

S2. Experimental

For the preparation of compound (I), a mixture of isatin (1 mmol), sarcosine (2 mmol) and cyclooctanone (1 mmol) in methanol (20 ml) was refluxed in a water bath for 6 h. After completion of the reaction as monitored by thin-layer chromatography, the excess solvent was removed under vacuum and the residue was subjected to flash column chromatography using petroleum ether–ethyl acetate (8:2 v/v) as eluant (yield 46%; m.p. 448–449 K).

For the preparation of (II), a mixture of isatin (1 mmol), sarcosine (2 mmol) and 1-methyltetrahydro-4(1H)-pyridinone (1 mmol) in methanol (20 ml) was refluxed in a water bath for 6 h. After completion of the reaction as monitored by thin-layer chromatography, the excess solvent was removed under vacuum and the residue was subjected to flash column chromatography using petroleum ether–ethyl acetate (8:2 v/v) as eluant (yield 57%; m.p. 403–404 K).

S3. Refinement

H atoms bound to atoms C15, C20, C35 and C40 of compound (I) were found in a difference Fourier map and their positional and isotropic displacement parameters were refined. The remaining H atoms were placed in calculated positions and allowed to ride on their parent atoms, with C—H = 0.93–0.97 Å and N—H = 0.86 Å, and with U_iso = 1.2U_eq(C,N) for CH₂, NH and CH groups, and 1.5U_eq(C) for CH₃ groups.

Computing details

For both compounds, data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The two independent molecules, (a) and (b), of the asymmetric unit of compound (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The two independent molecules, (a) and (b), of the asymmetric unit of compound (II), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level for molecule (a) and at the 20% probability level for molecule (b), for clarity. H atoms are shown as small spheres of arbitrary radii.
	Fig. 3. A partial packing view showing the intermolecular N—H···O and C—H···O interactions (dashed lines) in compound (I). H atoms and some ring atoms not involved in hydrogen-bonding interactions have been omitted for clarity.
	Fig. 4. A partial packing view showing the intermolecular N—H···O and N—H···N interactions (dashed lines) generating a graph-set motif of R1^2(5) in compound (II). H atoms and some ring atoms not involved in hydrogen-bonding interactions have been omitted for clarity.

(I) 1'-Methyl-2'',3''-dihydrocyclooctane-1-spiro-3'-pyrrolidine-2'-spiro-3''- 1H-indole-2,2''-dione

Crystal data

C19H24N2O2	F(000) = 1344
Mr = 312.40	Dx = 1.258 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 29.0670 (11) Å	θ = 2–25°
b = 11.2560 (9) Å	µ = 0.08 mm^−1
c = 10.1480 (7) Å	T = 293 K
β = 96.580 (5)°	Block, colourless
V = 3298.3 (4) Å^3	0.19 × 0.15 × 0.11 mm
Z = 8

Data collection

Nonius MACH3 four-circle diffractometer	3081 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
Graphite monochromator	θmax = 25.0°, θmin = 2.1°
ω scans	h = −34→34
Absorption correction: ψ scan (North et al., 1968)	k = −1→13
Tmin = 0.982, Tmax = 0.985	l = 0→12
6828 measured reflections	3 standard reflections every 60 min
5781 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.046P)^2 + 0.6618P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
5781 reflections	Δρmax = 0.19 e Å^−3
450 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (4)

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C2	0.33752 (10)	0.4598 (2)	0.4525 (2)	0.0535 (7)
H2A	0.3083	0.4852	0.4050	0.064*
H2B	0.3495	0.3939	0.4051	0.064*
C3	0.37209 (9)	0.5621 (2)	0.4662 (2)	0.0464 (7)
H3A	0.3576	0.6348	0.4309	0.056*
H3B	0.3983	0.5447	0.4183	0.056*
C4	0.38799 (8)	0.5756 (2)	0.6160 (2)	0.0334 (6)
C5	0.34430 (8)	0.5247 (2)	0.6762 (2)	0.0352 (6)
C6	0.28733 (9)	0.3670 (3)	0.6032 (3)	0.0598 (8)
H6A	0.2623	0.4207	0.5769	0.090*
H6B	0.2866	0.3446	0.6942	0.090*
H6C	0.2841	0.2974	0.5482	0.090*
C7	0.34906 (8)	0.4895 (2)	0.8204 (2)	0.0352 (6)
C8	0.37167 (9)	0.3939 (2)	0.8848 (3)	0.0455 (6)
H8	0.3888	0.3416	0.8389	0.055*
C9	0.36836 (10)	0.3772 (3)	1.0185 (3)	0.0599 (8)
H9	0.3836	0.3140	1.0635	0.072*
C10	0.34236 (12)	0.4545 (3)	1.0847 (3)	0.0682 (9)
H10	0.3411	0.4437	1.1751	0.082*
C11	0.31815 (10)	0.5477 (3)	1.0213 (3)	0.0578 (8)
H11	0.3001	0.5982	1.0666	0.069*
C12	0.32182 (9)	0.5626 (2)	0.8884 (2)	0.0405 (6)
C13	0.30682 (8)	0.6235 (2)	0.6733 (3)	0.0400 (6)
C14	0.42876 (8)	0.4914 (2)	0.6566 (2)	0.0362 (6)
C15	0.46100 (9)	0.5123 (3)	0.7829 (3)	0.0424 (6)
C16	0.50861 (9)	0.5584 (2)	0.7552 (3)	0.0559 (8)
H16A	0.5295	0.5530	0.8367	0.067*
H16B	0.5204	0.5060	0.6911	0.067*
C17	0.51004 (9)	0.6849 (3)	0.7037 (3)	0.0574 (8)
H17A	0.5420	0.7051	0.6949	0.069*
H17B	0.4995	0.7378	0.7694	0.069*
C18	0.48096 (9)	0.7082 (3)	0.5705 (3)	0.0552 (8)
H18A	0.4988	0.7583	0.5173	0.066*
H18B	0.4759	0.6331	0.5243	0.066*
C19	0.43398 (9)	0.7670 (2)	0.5781 (3)	0.0502 (7)
H19A	0.4395	0.8455	0.6159	0.060*
H19B	0.4192	0.7775	0.4882	0.060*
C20	0.39965 (9)	0.7038 (2)	0.6571 (3)	0.0368 (6)
C22	0.16927 (11)	0.4916 (3)	0.0569 (3)	0.0680 (9)
H22A	0.1598	0.4307	−0.0083	0.082*
H22B	0.1989	0.5237	0.0386	0.082*
C23	0.13306 (10)	0.5894 (3)	0.0529 (2)	0.0546 (7)
H23A	0.1081	0.5740	−0.0169	0.066*
H23B	0.1468	0.6657	0.0362	0.066*
C24	0.11470 (8)	0.5895 (2)	0.1891 (2)	0.0368 (6)
C25	0.15684 (8)	0.5308 (2)	0.2797 (2)	0.0376 (6)
C26	0.21582 (10)	0.3821 (3)	0.2335 (3)	0.0735 (10)
H26A	0.2204	0.3191	0.1727	0.110*
H26B	0.2146	0.3498	0.3205	0.110*
H26C	0.2410	0.4375	0.2358	0.110*
C27	0.14760 (8)	0.4771 (2)	0.4104 (2)	0.0350 (6)
C28	0.12501 (9)	0.3740 (2)	0.4387 (3)	0.0460 (7)
H28	0.1112	0.3264	0.3704	0.055*
C29	0.12322 (10)	0.3422 (3)	0.5700 (3)	0.0589 (8)
H29	0.1075	0.2737	0.5901	0.071*
C30	0.14457 (10)	0.4118 (3)	0.6707 (3)	0.0609 (8)
H30	0.1425	0.3904	0.7583	0.073*
C31	0.16890 (9)	0.5123 (2)	0.6443 (2)	0.0506 (7)
H31	0.1838	0.5581	0.7125	0.061*
C32	0.17033 (8)	0.5424 (2)	0.5139 (2)	0.0362 (6)
C33	0.19325 (8)	0.6283 (2)	0.3278 (3)	0.0437 (6)
C34	0.07330 (8)	0.5043 (2)	0.1890 (2)	0.0380 (6)
C35	0.03992 (9)	0.5158 (3)	0.2925 (3)	0.0432 (6)
C36	−0.00732 (9)	0.5636 (2)	0.2341 (3)	0.0552 (8)
H36A	−0.0182	0.5164	0.1569	0.066*
H36B	−0.0290	0.5524	0.2990	0.066*
C37	−0.00825 (9)	0.6934 (2)	0.1938 (3)	0.0577 (8)
H37A	0.0014	0.7407	0.2720	0.069*
H37B	−0.0400	0.7149	0.1633	0.069*
C38	0.02181 (9)	0.7270 (2)	0.0864 (3)	0.0536 (7)
H38A	0.0046	0.7822	0.0261	0.064*
H38B	0.0273	0.6561	0.0362	0.064*
C39	0.06856 (9)	0.7831 (2)	0.1344 (3)	0.0535 (7)
H39A	0.0843	0.7992	0.0571	0.064*
H39B	0.0627	0.8591	0.1742	0.064*
C40	0.10197 (10)	0.7142 (2)	0.2333 (3)	0.0423 (6)
N11	0.33136 (7)	0.42519 (18)	0.5882 (2)	0.0416 (5)
N12	0.29815 (7)	0.64376 (18)	0.7994 (2)	0.0485 (6)
H12	0.2804	0.6993	0.8224	0.058*
N21	0.17267 (7)	0.44277 (19)	0.1903 (2)	0.0486 (6)
N22	0.19552 (7)	0.63443 (18)	0.4617 (2)	0.0448 (5)
H22	0.2106	0.6881	0.5091	0.054*
O11	0.28791 (6)	0.67341 (16)	0.57406 (19)	0.0533 (5)
O12	0.43616 (6)	0.40761 (16)	0.58697 (18)	0.0547 (5)
O21	0.21585 (6)	0.68809 (18)	0.25862 (19)	0.0653 (6)
O22	0.06641 (6)	0.42817 (16)	0.10462 (18)	0.0561 (5)
H20A	0.4097 (7)	0.7079 (18)	0.751 (2)	0.031 (6)*
H15B	0.4650 (8)	0.436 (2)	0.825 (2)	0.044 (7)*
H15A	0.4464 (8)	0.567 (2)	0.844 (2)	0.042 (7)*
H20B	0.3714 (9)	0.752 (2)	0.646 (2)	0.050 (7)*
H40A	0.0893 (7)	0.7105 (19)	0.319 (2)	0.037 (6)*
H40B	0.1303 (9)	0.760 (2)	0.248 (2)	0.046 (7)*
H35B	0.0349 (8)	0.437 (2)	0.321 (2)	0.043 (7)*
H35A	0.0531 (8)	0.567 (2)	0.370 (2)	0.051 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0560 (18)	0.0619 (19)	0.0408 (16)	−0.0044 (15)	−0.0026 (13)	−0.0072 (14)
C3	0.0482 (16)	0.0576 (17)	0.0333 (14)	−0.0006 (14)	0.0044 (12)	0.0002 (12)
C4	0.0336 (14)	0.0383 (14)	0.0285 (12)	0.0014 (11)	0.0043 (10)	0.0014 (10)
C5	0.0351 (14)	0.0335 (14)	0.0371 (13)	0.0029 (11)	0.0043 (10)	−0.0033 (11)
C6	0.0450 (17)	0.0582 (19)	0.076 (2)	−0.0124 (15)	0.0068 (15)	−0.0102 (16)
C7	0.0340 (14)	0.0344 (13)	0.0381 (13)	−0.0034 (11)	0.0086 (10)	−0.0005 (11)
C8	0.0437 (16)	0.0451 (16)	0.0490 (16)	−0.0004 (13)	0.0109 (12)	0.0038 (13)
C9	0.069 (2)	0.0571 (19)	0.0531 (19)	−0.0070 (16)	0.0030 (15)	0.0162 (15)
C10	0.092 (3)	0.074 (2)	0.0402 (17)	−0.021 (2)	0.0157 (17)	0.0047 (17)
C11	0.071 (2)	0.0552 (19)	0.0515 (18)	−0.0098 (16)	0.0265 (15)	−0.0126 (15)
C12	0.0432 (15)	0.0356 (14)	0.0445 (15)	−0.0070 (12)	0.0123 (12)	−0.0026 (12)
C13	0.0296 (13)	0.0363 (14)	0.0536 (17)	−0.0027 (11)	0.0030 (12)	0.0001 (13)
C14	0.0341 (14)	0.0349 (14)	0.0410 (14)	−0.0002 (11)	0.0105 (11)	−0.0030 (12)
C15	0.0431 (16)	0.0360 (15)	0.0470 (16)	0.0047 (13)	0.0005 (12)	0.0013 (14)
C16	0.0385 (17)	0.0573 (19)	0.0701 (19)	−0.0008 (14)	−0.0017 (14)	−0.0084 (15)
C17	0.0419 (16)	0.0592 (19)	0.071 (2)	−0.0121 (14)	0.0063 (14)	−0.0033 (16)
C18	0.0554 (18)	0.0599 (19)	0.0533 (18)	−0.0151 (15)	0.0188 (14)	−0.0003 (15)
C19	0.0568 (18)	0.0452 (16)	0.0489 (16)	−0.0097 (14)	0.0068 (13)	0.0077 (13)
C20	0.0403 (15)	0.0332 (14)	0.0370 (16)	0.0033 (12)	0.0040 (12)	0.0030 (11)
C22	0.068 (2)	0.090 (2)	0.0484 (18)	0.0082 (19)	0.0163 (15)	−0.0036 (17)
C23	0.0588 (18)	0.0636 (19)	0.0418 (16)	−0.0045 (15)	0.0070 (13)	0.0040 (14)
C24	0.0391 (15)	0.0384 (14)	0.0320 (13)	−0.0037 (11)	0.0000 (11)	0.0003 (11)
C25	0.0338 (14)	0.0401 (14)	0.0383 (14)	−0.0023 (11)	0.0014 (11)	−0.0013 (11)
C26	0.0516 (19)	0.086 (2)	0.082 (2)	0.0237 (18)	0.0048 (16)	−0.0161 (19)
C27	0.0283 (13)	0.0321 (13)	0.0436 (14)	0.0020 (11)	−0.0001 (11)	0.0016 (11)
C28	0.0463 (16)	0.0368 (15)	0.0526 (17)	−0.0033 (13)	−0.0043 (13)	0.0042 (13)
C29	0.0622 (19)	0.0495 (18)	0.065 (2)	−0.0055 (15)	0.0052 (15)	0.0218 (15)
C30	0.068 (2)	0.066 (2)	0.0482 (18)	0.0033 (17)	0.0035 (15)	0.0189 (16)
C31	0.0556 (18)	0.0521 (17)	0.0420 (16)	0.0043 (15)	−0.0040 (13)	−0.0027 (13)
C32	0.0315 (13)	0.0340 (14)	0.0420 (15)	0.0021 (11)	−0.0008 (11)	0.0006 (11)
C33	0.0319 (14)	0.0444 (16)	0.0541 (18)	−0.0046 (12)	0.0014 (12)	0.0055 (13)
C34	0.0370 (14)	0.0316 (14)	0.0425 (14)	0.0045 (11)	−0.0070 (11)	−0.0003 (12)
C35	0.0400 (15)	0.0332 (15)	0.0563 (17)	−0.0040 (12)	0.0051 (13)	−0.0002 (14)
C36	0.0398 (16)	0.0499 (18)	0.076 (2)	0.0044 (13)	0.0053 (14)	−0.0007 (15)
C37	0.0488 (18)	0.0513 (18)	0.071 (2)	0.0131 (14)	−0.0004 (15)	0.0005 (15)
C38	0.0593 (18)	0.0465 (16)	0.0511 (17)	0.0121 (14)	−0.0103 (14)	0.0031 (13)
C39	0.0656 (19)	0.0393 (15)	0.0545 (17)	0.0041 (14)	0.0020 (14)	0.0091 (13)
C40	0.0471 (17)	0.0349 (15)	0.0440 (17)	−0.0074 (13)	0.0007 (13)	0.0008 (12)
N11	0.0387 (12)	0.0435 (12)	0.0419 (12)	−0.0039 (10)	0.0019 (9)	−0.0063 (10)
N12	0.0462 (13)	0.0419 (13)	0.0605 (15)	0.0075 (11)	0.0199 (11)	−0.0069 (11)
N21	0.0402 (13)	0.0571 (14)	0.0480 (13)	0.0096 (11)	0.0028 (10)	−0.0084 (11)
N22	0.0414 (13)	0.0432 (13)	0.0475 (14)	−0.0117 (10)	−0.0053 (10)	−0.0029 (10)
O11	0.0410 (10)	0.0515 (12)	0.0646 (13)	0.0060 (9)	−0.0059 (9)	0.0097 (10)
O12	0.0503 (12)	0.0500 (12)	0.0639 (12)	0.0069 (9)	0.0067 (9)	−0.0222 (10)
O21	0.0534 (12)	0.0758 (15)	0.0666 (13)	−0.0281 (11)	0.0069 (10)	0.0133 (11)
O22	0.0519 (12)	0.0473 (12)	0.0664 (13)	−0.0010 (9)	−0.0051 (9)	−0.0228 (10)

Geometric parameters (Å, º)

C2—N11	1.462 (3)	C22—C23	1.520 (4)
C2—C3	1.524 (3)	C22—H22A	0.9700
C2—H2A	0.9700	C22—H22B	0.9700
C2—H2B	0.9700	C23—C24	1.538 (3)
C3—C4	1.545 (3)	C23—H23A	0.9700
C3—H3A	0.9700	C23—H23B	0.9700
C3—H3B	0.9700	C24—C40	1.532 (3)
C4—C20	1.530 (3)	C24—C34	1.538 (3)
C4—C14	1.537 (3)	C24—C25	1.588 (3)
C4—C5	1.579 (3)	C25—N21	1.453 (3)
C5—N11	1.455 (3)	C25—C27	1.510 (3)
C5—C7	1.507 (3)	C25—C33	1.564 (3)
C5—C13	1.554 (3)	C26—N21	1.451 (3)
C6—N11	1.461 (3)	C26—H26A	0.9600
C6—H6A	0.9600	C26—H26B	0.9600
C6—H6B	0.9600	C26—H26C	0.9600
C6—H6C	0.9600	C27—C28	1.379 (3)
C7—C12	1.381 (3)	C27—C32	1.386 (3)
C7—C8	1.385 (3)	C28—C29	1.387 (4)
C8—C9	1.384 (4)	C28—H28	0.9300
C8—H8	0.9300	C29—C30	1.377 (4)
C9—C10	1.377 (4)	C29—H29	0.9300
C9—H9	0.9300	C30—C31	1.377 (4)
C10—C11	1.380 (4)	C30—H30	0.9300
C10—H10	0.9300	C31—C32	1.371 (3)
C11—C12	1.376 (3)	C31—H31	0.9300
C11—H11	0.9300	C32—N22	1.407 (3)
C12—N12	1.407 (3)	C33—O21	1.218 (3)
C13—O11	1.227 (3)	C33—N22	1.354 (3)
C13—N12	1.352 (3)	C34—O22	1.212 (3)
C14—O12	1.212 (3)	C34—C35	1.515 (3)
C14—C15	1.517 (3)	C35—C36	1.530 (4)
C15—C16	1.534 (4)	C35—H35B	0.95 (2)
C15—H15B	0.96 (2)	C35—H35A	1.01 (3)
C15—H15A	1.00 (2)	C36—C37	1.517 (4)
C16—C17	1.519 (4)	C36—H36A	0.9700
C16—H16A	0.9700	C36—H36B	0.9700
C16—H16B	0.9700	C37—C38	1.521 (4)
C17—C18	1.532 (4)	C37—H37A	0.9700
C17—H17A	0.9700	C37—H37B	0.9700
C17—H17B	0.9700	C38—C39	1.527 (4)
C18—C19	1.527 (4)	C38—H38A	0.9700
C18—H18A	0.9700	C38—H38B	0.9700
C18—H18B	0.9700	C39—C40	1.526 (4)
C19—C20	1.525 (3)	C39—H39A	0.9700
C19—H19A	0.9700	C39—H39B	0.9700
C19—H19B	0.9700	C40—H40A	0.99 (2)
C20—H20A	0.97 (2)	C40—H40B	0.97 (2)
C20—H20B	0.98 (2)	N12—H12	0.8600
C22—N21	1.454 (3)	N22—H22	0.8600
N11—C2—C3	105.44 (19)	C22—C23—C24	106.7 (2)
N11—C2—H2A	110.7	C22—C23—H23A	110.4
C3—C2—H2A	110.7	C24—C23—H23A	110.4
N11—C2—H2B	110.7	C22—C23—H23B	110.4
C3—C2—H2B	110.7	C24—C23—H23B	110.4
H2A—C2—H2B	108.8	H23A—C23—H23B	108.6
C2—C3—C4	106.48 (19)	C40—C24—C23	112.6 (2)
C2—C3—H3A	110.4	C40—C24—C34	110.9 (2)
C4—C3—H3A	110.4	C23—C24—C34	110.5 (2)
C2—C3—H3B	110.4	C40—C24—C25	114.07 (19)
C4—C3—H3B	110.4	C23—C24—C25	101.28 (19)
H3A—C3—H3B	108.6	C34—C24—C25	107.03 (18)
C20—C4—C14	111.68 (19)	N21—C25—C27	112.1 (2)
C20—C4—C3	113.1 (2)	N21—C25—C33	115.0 (2)
C14—C4—C3	109.74 (19)	C27—C25—C33	100.87 (19)
C20—C4—C5	113.56 (18)	N21—C25—C24	101.60 (18)
C14—C4—C5	107.59 (18)	C27—C25—C24	118.15 (19)
C3—C4—C5	100.49 (18)	C33—C25—C24	109.77 (19)
N11—C5—C7	112.43 (19)	N21—C26—H26A	109.5
N11—C5—C13	114.07 (19)	N21—C26—H26B	109.5
C7—C5—C13	101.13 (18)	H26A—C26—H26B	109.5
N11—C5—C4	101.80 (17)	N21—C26—H26C	109.5
C7—C5—C4	118.89 (19)	H26A—C26—H26C	109.5
C13—C5—C4	109.04 (18)	H26B—C26—H26C	109.5
N11—C6—H6A	109.5	C28—C27—C32	119.1 (2)
N11—C6—H6B	109.5	C28—C27—C25	131.0 (2)
H6A—C6—H6B	109.5	C32—C27—C25	109.6 (2)
N11—C6—H6C	109.5	C27—C28—C29	119.2 (2)
H6A—C6—H6C	109.5	C27—C28—H28	120.4
H6B—C6—H6C	109.5	C29—C28—H28	120.4
C12—C7—C8	119.7 (2)	C30—C29—C28	120.2 (3)
C12—C7—C5	109.5 (2)	C30—C29—H29	119.9
C8—C7—C5	130.5 (2)	C28—C29—H29	119.9
C9—C8—C7	119.1 (2)	C31—C30—C29	121.4 (3)
C9—C8—H8	120.5	C31—C30—H30	119.3
C7—C8—H8	120.5	C29—C30—H30	119.3
C10—C9—C8	119.8 (3)	C32—C31—C30	117.6 (3)
C10—C9—H9	120.1	C32—C31—H31	121.2
C8—C9—H9	120.1	C30—C31—H31	121.2
C9—C10—C11	122.1 (3)	C31—C32—C27	122.4 (2)
C9—C10—H10	118.9	C31—C32—N22	128.4 (2)
C11—C10—H10	118.9	C27—C32—N22	109.2 (2)
C12—C11—C10	117.2 (3)	O21—C33—N22	125.7 (2)
C12—C11—H11	121.4	O21—C33—C25	126.7 (2)
C10—C11—H11	121.4	N22—C33—C25	107.6 (2)
C11—C12—C7	122.0 (3)	O22—C34—C35	118.9 (2)
C11—C12—N12	128.4 (2)	O22—C34—C24	120.5 (2)
C7—C12—N12	109.4 (2)	C35—C34—C24	120.6 (2)
O11—C13—N12	125.8 (2)	C34—C35—C36	112.3 (2)
O11—C13—C5	126.2 (2)	C34—C35—H35B	105.3 (14)
N12—C13—C5	108.0 (2)	C36—C35—H35B	106.6 (14)
O12—C14—C15	118.7 (2)	C34—C35—H35A	111.8 (13)
O12—C14—C4	120.4 (2)	C36—C35—H35A	110.1 (14)
C15—C14—C4	120.9 (2)	H35B—C35—H35A	111 (2)
C14—C15—C16	112.4 (2)	C37—C36—C35	115.5 (2)
C14—C15—H15B	105.4 (14)	C37—C36—H36A	108.4
C16—C15—H15B	108.6 (14)	C35—C36—H36A	108.4
C14—C15—H15A	110.6 (13)	C37—C36—H36B	108.4
C16—C15—H15A	111.2 (13)	C35—C36—H36B	108.4
H15B—C15—H15A	108.4 (19)	H36A—C36—H36B	107.5
C17—C16—C15	116.2 (2)	C36—C37—C38	116.1 (2)
C17—C16—H16A	108.2	C36—C37—H37A	108.3
C15—C16—H16A	108.2	C38—C37—H37A	108.3
C17—C16—H16B	108.2	C36—C37—H37B	108.3
C15—C16—H16B	108.2	C38—C37—H37B	108.3
H16A—C16—H16B	107.4	H37A—C37—H37B	107.4
C16—C17—C18	115.5 (2)	C37—C38—C39	116.0 (2)
C16—C17—H17A	108.4	C37—C38—H38A	108.3
C18—C17—H17A	108.4	C39—C38—H38A	108.3
C16—C17—H17B	108.4	C37—C38—H38B	108.3
C18—C17—H17B	108.4	C39—C38—H38B	108.3
H17A—C17—H17B	107.5	H38A—C38—H38B	107.4
C19—C18—C17	115.8 (2)	C40—C39—C38	118.4 (2)
C19—C18—H18A	108.3	C40—C39—H39A	107.7
C17—C18—H18A	108.3	C38—C39—H39A	107.7
C19—C18—H18B	108.3	C40—C39—H39B	107.7
C17—C18—H18B	108.3	C38—C39—H39B	107.7
H18A—C18—H18B	107.4	H39A—C39—H39B	107.1
C20—C19—C18	117.9 (2)	C39—C40—C24	115.5 (2)
C20—C19—H19A	107.8	C39—C40—H40A	109.2 (13)
C18—C19—H19A	107.8	C24—C40—H40A	110.4 (13)
C20—C19—H19B	107.8	C39—C40—H40B	107.1 (14)
C18—C19—H19B	107.8	C24—C40—H40B	107.6 (14)
H19A—C19—H19B	107.2	H40A—C40—H40B	106.6 (19)
C19—C20—C4	115.8 (2)	C5—N11—C6	116.7 (2)
C19—C20—H20A	110.8 (12)	C5—N11—C2	108.78 (19)
C4—C20—H20A	110.2 (13)	C6—N11—C2	114.9 (2)
C19—C20—H20B	105.9 (14)	C13—N12—C12	111.5 (2)
C4—C20—H20B	109.6 (14)	C13—N12—H12	124.2
H20A—C20—H20B	103.6 (18)	C12—N12—H12	124.2
N21—C22—C23	105.8 (2)	C26—N21—C25	117.2 (2)
N21—C22—H22A	110.6	C26—N21—C22	115.0 (2)
C23—C22—H22A	110.6	C25—N21—C22	109.3 (2)
N21—C22—H22B	110.6	C33—N22—C32	111.9 (2)
C23—C22—H22B	110.6	C33—N22—H22	124.0
H22A—C22—H22B	108.7	C32—N22—H22	124.0
N11—C2—C3—C4	4.7 (3)	C34—C24—C25—C33	−159.00 (19)
C2—C3—C4—C20	−148.2 (2)	N21—C25—C27—C28	−44.5 (3)
C2—C3—C4—C14	86.4 (2)	C33—C25—C27—C28	−167.3 (2)
C2—C3—C4—C5	−26.8 (2)	C24—C25—C27—C28	73.1 (3)
C20—C4—C5—N11	160.48 (19)	N21—C25—C27—C32	129.1 (2)
C14—C4—C5—N11	−75.4 (2)	C33—C25—C27—C32	6.3 (2)
C3—C4—C5—N11	39.4 (2)	C24—C25—C27—C32	−113.3 (2)
C20—C4—C5—C7	−75.4 (3)	C32—C27—C28—C29	3.9 (4)
C14—C4—C5—C7	48.7 (3)	C25—C27—C28—C29	177.0 (2)
C3—C4—C5—C7	163.5 (2)	C27—C28—C29—C30	−1.3 (4)
C20—C4—C5—C13	39.6 (3)	C28—C29—C30—C31	−1.4 (4)
C14—C4—C5—C13	163.75 (19)	C29—C30—C31—C32	1.4 (4)
C3—C4—C5—C13	−81.5 (2)	C30—C31—C32—C27	1.4 (4)
N11—C5—C7—C12	−126.3 (2)	C30—C31—C32—N22	−174.6 (2)
C13—C5—C7—C12	−4.3 (2)	C28—C27—C32—C31	−4.0 (4)
C4—C5—C7—C12	115.0 (2)	C25—C27—C32—C31	−178.5 (2)
N11—C5—C7—C8	46.9 (3)	C28—C27—C32—N22	172.6 (2)
C13—C5—C7—C8	169.0 (2)	C25—C27—C32—N22	−1.9 (3)
C4—C5—C7—C8	−71.8 (3)	N21—C25—C33—O21	50.1 (3)
C12—C7—C8—C9	−3.3 (4)	C27—C25—C33—O21	170.9 (3)
C5—C7—C8—C9	−175.9 (2)	C24—C25—C33—O21	−63.7 (3)
C7—C8—C9—C10	0.8 (4)	N21—C25—C33—N22	−129.6 (2)
C8—C9—C10—C11	1.7 (5)	C27—C25—C33—N22	−8.7 (2)
C9—C10—C11—C12	−1.6 (5)	C24—C25—C33—N22	116.7 (2)
C10—C11—C12—C7	−1.0 (4)	C40—C24—C34—O22	143.7 (2)
C10—C11—C12—N12	174.6 (3)	C23—C24—C34—O22	18.1 (3)
C8—C7—C12—C11	3.5 (4)	C25—C24—C34—O22	−91.4 (3)
C5—C7—C12—C11	177.5 (2)	C40—C24—C34—C35	−35.1 (3)
C8—C7—C12—N12	−172.9 (2)	C23—C24—C34—C35	−160.7 (2)
C5—C7—C12—N12	1.2 (3)	C25—C24—C34—C35	89.8 (2)
N11—C5—C13—O11	−52.2 (3)	O22—C34—C35—C36	−70.1 (3)
C7—C5—C13—O11	−173.1 (2)	C24—C34—C35—C36	108.7 (3)
C4—C5—C13—O11	60.8 (3)	C34—C35—C36—C37	−70.7 (3)
N11—C5—C13—N12	126.9 (2)	C35—C36—C37—C38	61.4 (3)
C7—C5—C13—N12	6.0 (2)	C36—C37—C38—C39	−99.4 (3)
C4—C5—C13—N12	−120.0 (2)	C37—C38—C39—C40	56.9 (3)
C20—C4—C14—O12	−145.1 (2)	C38—C39—C40—C24	56.3 (3)
C3—C4—C14—O12	−18.8 (3)	C23—C24—C40—C39	53.5 (3)
C5—C4—C14—O12	89.6 (2)	C34—C24—C40—C39	−70.9 (3)
C20—C4—C14—C15	33.8 (3)	C25—C24—C40—C39	168.2 (2)
C3—C4—C14—C15	160.1 (2)	C7—C5—N11—C6	60.5 (3)
C5—C4—C14—C15	−91.4 (3)	C13—C5—N11—C6	−53.9 (3)
O12—C14—C15—C16	72.0 (3)	C4—C5—N11—C6	−171.2 (2)
C4—C14—C15—C16	−106.9 (3)	C7—C5—N11—C2	−167.54 (19)
C14—C15—C16—C17	70.7 (3)	C13—C5—N11—C2	78.1 (2)
C15—C16—C17—C18	−61.4 (3)	C4—C5—N11—C2	−39.2 (2)
C16—C17—C18—C19	100.0 (3)	C3—C2—N11—C5	22.2 (3)
C17—C18—C19—C20	−58.2 (3)	C3—C2—N11—C6	155.2 (2)
C18—C19—C20—C4	−55.2 (3)	O11—C13—N12—C12	173.3 (2)
C14—C4—C20—C19	71.7 (3)	C5—C13—N12—C12	−5.8 (3)
C3—C4—C20—C19	−52.7 (3)	C11—C12—N12—C13	−173.0 (2)
C5—C4—C20—C19	−166.4 (2)	C7—C12—N12—C13	3.1 (3)
N21—C22—C23—C24	−2.4 (3)	C27—C25—N21—C26	−61.7 (3)
C22—C23—C24—C40	146.2 (2)	C33—C25—N21—C26	52.8 (3)
C22—C23—C24—C34	−89.2 (3)	C24—C25—N21—C26	171.2 (2)
C22—C23—C24—C25	24.0 (3)	C27—C25—N21—C22	165.2 (2)
C40—C24—C25—N21	−158.1 (2)	C33—C25—N21—C22	−80.4 (3)
C23—C24—C25—N21	−36.9 (2)	C24—C25—N21—C22	38.1 (3)
C34—C24—C25—N21	78.9 (2)	C23—C22—N21—C26	−157.5 (2)
C40—C24—C25—C27	78.8 (3)	C23—C22—N21—C25	−23.2 (3)
C23—C24—C25—C27	−160.0 (2)	O21—C33—N22—C32	−171.2 (2)
C34—C24—C25—C27	−44.2 (3)	C25—C33—N22—C32	8.4 (3)
C40—C24—C25—C33	−36.0 (3)	C31—C32—N22—C33	172.0 (2)
C23—C24—C25—C33	85.2 (2)	C27—C32—N22—C33	−4.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O11^i	0.93	2.60	3.320 (3)	135
N12—H12···O21^i	0.86	2.29	3.041 (3)	145
C29—H29···O22^ii	0.93	2.58	3.499 (3)	170
N22—H22···O11	0.86	2.28	2.829 (3)	122

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+1/2, z+1/2.

(II) 1,1'-dimethyl-2'',3''-dihydropiperidine-3-spiro-3'-pyrrolidine-2'-spiro-3''- 1H-indole-4,2''-dione

Crystal data

C17H21N3O2	F(000) = 1280
Mr = 299.37	Dx = 1.231 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 9.5194 (7) Å	θ = 2–25°
b = 21.8847 (14) Å	µ = 0.08 mm^−1
c = 15.5413 (11) Å	T = 293 K
β = 93.86 (4)°	Block, colourless
V = 3230.3 (4) Å^3	0.19 × 0.16 × 0.11 mm
Z = 8

Data collection

Nonius MACH3 four-circle diffractometer	2327 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 25.0°, θmin = 2.3°
ω scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = −1→26
Tmin = 0.985, Tmax = 0.991	l = −18→18
6392 measured reflections	3 standard reflections every 60 min
5685 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.134	w = 1/[σ^2(Fo^2) + (0.0525P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
5685 reflections	Δρmax = 0.14 e Å^−3
402 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0020 (3)

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C2	1.0741 (3)	0.26284 (14)	0.1797 (2)	0.0579 (9)
H2A	1.0432	0.3016	0.1549	0.070*
H2B	1.1613	0.2508	0.1556	0.070*
C3	1.0915 (3)	0.26654 (15)	0.2757 (2)	0.0635 (9)
H3A	1.1137	0.3081	0.2937	0.076*
H3B	1.1673	0.2400	0.2975	0.076*
C4	0.9507 (3)	0.24613 (14)	0.31056 (19)	0.0473 (8)
C5	0.8586 (3)	0.22834 (12)	0.22587 (18)	0.0417 (7)
C6	0.9133 (3)	0.20840 (15)	0.07511 (19)	0.0679 (10)
H6A	0.8685	0.2455	0.0549	0.102*
H6B	0.8464	0.1755	0.0710	0.102*
H6C	0.9903	0.1992	0.0405	0.102*
C7	0.7442 (3)	0.27502 (13)	0.20191 (18)	0.0444 (8)
C8	0.7502 (3)	0.33755 (14)	0.1880 (2)	0.0575 (9)
H8	0.8366	0.3571	0.1860	0.069*
C9	0.6257 (4)	0.37054 (15)	0.1771 (2)	0.0714 (10)
H9	0.6288	0.4124	0.1674	0.086*
C10	0.4983 (4)	0.34169 (17)	0.1807 (2)	0.0746 (11)
H10	0.4160	0.3646	0.1745	0.089*
C11	0.4896 (3)	0.27915 (16)	0.1932 (2)	0.0658 (10)
H11	0.4030	0.2597	0.1952	0.079*
C12	0.6140 (3)	0.24689 (14)	0.20275 (19)	0.0478 (8)
C13	0.7698 (3)	0.16872 (14)	0.22914 (18)	0.0452 (8)
C14	0.8833 (4)	0.29713 (17)	0.3629 (2)	0.0626 (9)
C15	0.7596 (4)	0.27877 (18)	0.4110 (2)	0.0809 (12)
H15A	0.6790	0.2720	0.3706	0.097*
H15B	0.7362	0.3116	0.4496	0.097*
C16	0.7900 (4)	0.2212 (2)	0.4628 (2)	0.0896 (13)
H16A	0.8607	0.2294	0.5092	0.108*
H16B	0.7051	0.2074	0.4879	0.108*
C17	0.9715 (3)	0.19168 (16)	0.3717 (2)	0.0625 (9)
H17A	1.0090	0.1574	0.3409	0.075*
H17B	1.0393	0.2024	0.4187	0.075*
C18	0.8501 (4)	0.11399 (19)	0.4463 (2)	0.1040 (15)
H18A	0.8676	0.0838	0.4035	0.156*
H18B	0.7632	0.1048	0.4715	0.156*
H18C	0.9258	0.1137	0.4904	0.156*
C22	0.5710 (3)	0.00910 (16)	0.1724 (3)	0.0762 (11)
H22A	0.6658	0.0206	0.1598	0.091*
H22B	0.5413	−0.0255	0.1366	0.091*
C23	0.5629 (4)	−0.00542 (18)	0.2660 (2)	0.0858 (12)
H23A	0.6419	0.0127	0.2994	0.103*
H23B	0.5657	−0.0493	0.2748	0.103*
C24	0.4236 (3)	0.02079 (13)	0.29467 (19)	0.0505 (8)
C25	0.3514 (3)	0.04680 (13)	0.20826 (18)	0.0433 (7)
C26	0.4414 (4)	0.07608 (18)	0.0682 (2)	0.0886 (12)
H26A	0.5274	0.0841	0.0412	0.133*
H26B	0.3828	0.1118	0.0643	0.133*
H26C	0.3930	0.0426	0.0395	0.133*
C27	0.2383 (3)	0.00515 (13)	0.16797 (18)	0.0480 (8)
C28	0.2402 (4)	−0.05540 (15)	0.1428 (2)	0.0675 (10)
H28	0.3236	−0.0776	0.1471	0.081*
C29	0.1156 (5)	−0.08243 (18)	0.1108 (3)	0.0875 (12)
H29	0.1159	−0.1229	0.0927	0.105*
C30	−0.0079 (5)	−0.0502 (2)	0.1056 (3)	0.0919 (13)
H30	−0.0902	−0.0696	0.0848	0.110*
C31	−0.0138 (4)	0.01070 (18)	0.1304 (2)	0.0758 (11)
H31	−0.0977	0.0326	0.1263	0.091*
C32	0.1111 (3)	0.03676 (15)	0.16123 (19)	0.0530 (8)
C33	0.2710 (3)	0.10768 (14)	0.21447 (18)	0.0446 (8)
C34	0.3331 (4)	−0.02676 (16)	0.3371 (2)	0.0687 (10)
C35	0.2077 (4)	−0.00189 (17)	0.3783 (2)	0.0784 (11)
H35A	0.1602	−0.0345	0.4070	0.094*
H35B	0.1420	0.0156	0.3347	0.094*
C36	0.2558 (4)	0.04678 (18)	0.4434 (2)	0.0796 (11)
H36A	0.1751	0.0642	0.4694	0.096*
H36B	0.3177	0.0289	0.4887	0.096*
C37	0.4544 (3)	0.06989 (14)	0.3636 (2)	0.0596 (9)
H37A	0.5153	0.0527	0.4099	0.072*
H37B	0.5048	0.1033	0.3385	0.072*
C38	0.3641 (4)	0.14679 (18)	0.4536 (2)	0.1042 (15)
H38A	0.4361	0.1359	0.4971	0.156*
H38B	0.2815	0.1600	0.4806	0.156*
H38C	0.3973	0.1793	0.4189	0.156*
N11	0.9662 (2)	0.21603 (10)	0.16515 (15)	0.0456 (6)
N12	0.6314 (2)	0.18415 (11)	0.21779 (15)	0.0548 (7)
H12	0.5631	0.1586	0.2196	0.066*
N13	0.8406 (3)	0.17397 (15)	0.40622 (18)	0.0716 (8)
N21	0.4736 (3)	0.06056 (11)	0.15870 (16)	0.0571 (7)
N22	0.1329 (3)	0.09680 (11)	0.19094 (15)	0.0529 (7)
H22	0.0671	0.1235	0.1939	0.063*
N23	0.3296 (3)	0.09385 (13)	0.39923 (17)	0.0632 (8)
O11	0.8175 (2)	0.11725 (9)	0.23209 (14)	0.0591 (6)
O12	0.9343 (3)	0.34743 (12)	0.36985 (17)	0.0915 (9)
O21	0.3236 (2)	0.15727 (9)	0.23035 (14)	0.0587 (6)
O22	0.3664 (3)	−0.07988 (11)	0.34333 (18)	0.1111 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.051 (2)	0.049 (2)	0.075 (3)	−0.0049 (17)	0.0128 (18)	0.0109 (18)
C3	0.0479 (19)	0.065 (2)	0.078 (3)	−0.0123 (18)	0.0038 (18)	−0.0126 (19)
C4	0.0446 (18)	0.0476 (19)	0.0495 (19)	−0.0009 (16)	0.0025 (15)	−0.0023 (16)
C5	0.0379 (17)	0.0365 (18)	0.0511 (19)	0.0024 (14)	0.0064 (15)	0.0024 (15)
C6	0.080 (2)	0.073 (3)	0.051 (2)	0.000 (2)	0.0128 (18)	0.0029 (18)
C7	0.0466 (19)	0.0387 (19)	0.0477 (19)	−0.0007 (16)	0.0011 (15)	0.0019 (15)
C8	0.056 (2)	0.043 (2)	0.074 (2)	−0.0033 (18)	0.0040 (18)	0.0032 (18)
C9	0.074 (3)	0.045 (2)	0.094 (3)	0.012 (2)	−0.003 (2)	0.007 (2)
C10	0.058 (2)	0.069 (3)	0.096 (3)	0.021 (2)	−0.003 (2)	0.014 (2)
C11	0.046 (2)	0.065 (3)	0.085 (3)	0.0004 (19)	−0.0022 (18)	0.017 (2)
C12	0.045 (2)	0.0425 (19)	0.055 (2)	−0.0019 (17)	−0.0019 (16)	0.0103 (16)
C13	0.048 (2)	0.041 (2)	0.0459 (19)	−0.0029 (17)	0.0019 (15)	0.0050 (15)
C14	0.065 (2)	0.067 (3)	0.055 (2)	0.003 (2)	−0.0029 (18)	−0.0074 (19)
C15	0.077 (3)	0.101 (3)	0.067 (2)	0.014 (2)	0.016 (2)	−0.016 (2)
C16	0.083 (3)	0.132 (4)	0.056 (2)	−0.004 (3)	0.014 (2)	0.003 (3)
C17	0.054 (2)	0.076 (2)	0.056 (2)	0.0021 (19)	−0.0035 (17)	0.0057 (19)
C18	0.108 (3)	0.110 (4)	0.092 (3)	−0.017 (3)	−0.009 (3)	0.055 (3)
C22	0.057 (2)	0.061 (2)	0.113 (3)	0.0084 (19)	0.022 (2)	−0.015 (2)
C23	0.077 (3)	0.079 (3)	0.100 (3)	0.030 (2)	−0.006 (2)	−0.001 (2)
C24	0.055 (2)	0.0371 (18)	0.059 (2)	0.0084 (16)	−0.0026 (16)	0.0022 (16)
C25	0.0429 (17)	0.0359 (18)	0.0515 (19)	0.0047 (15)	0.0059 (15)	−0.0028 (15)
C26	0.099 (3)	0.103 (3)	0.067 (3)	−0.003 (2)	0.033 (2)	0.008 (2)
C27	0.059 (2)	0.0365 (18)	0.0490 (19)	−0.0047 (16)	0.0078 (16)	−0.0057 (15)
C28	0.075 (2)	0.052 (2)	0.075 (2)	−0.001 (2)	−0.0013 (19)	−0.0158 (19)
C29	0.104 (3)	0.057 (3)	0.101 (3)	−0.018 (3)	0.000 (3)	−0.030 (2)
C30	0.079 (3)	0.088 (3)	0.108 (3)	−0.027 (3)	−0.006 (2)	−0.035 (3)
C31	0.056 (2)	0.083 (3)	0.088 (3)	−0.009 (2)	−0.003 (2)	−0.015 (2)
C32	0.049 (2)	0.055 (2)	0.054 (2)	−0.0027 (18)	0.0025 (17)	−0.0029 (17)
C33	0.048 (2)	0.0384 (19)	0.0477 (19)	−0.0013 (16)	0.0032 (15)	0.0047 (15)
C34	0.093 (3)	0.047 (2)	0.063 (2)	−0.011 (2)	−0.015 (2)	0.0107 (19)
C35	0.092 (3)	0.077 (3)	0.067 (2)	−0.025 (2)	0.010 (2)	0.014 (2)
C36	0.085 (3)	0.097 (3)	0.058 (2)	0.001 (2)	0.011 (2)	0.010 (2)
C37	0.062 (2)	0.054 (2)	0.060 (2)	−0.0025 (18)	−0.0115 (18)	0.0051 (18)
C38	0.126 (4)	0.091 (3)	0.092 (3)	0.008 (3)	−0.019 (3)	−0.041 (3)
N11	0.0450 (14)	0.0436 (15)	0.0489 (16)	−0.0016 (13)	0.0077 (12)	0.0018 (12)
N12	0.0421 (16)	0.0479 (17)	0.0736 (19)	−0.0107 (14)	−0.0012 (14)	0.0185 (14)
N13	0.071 (2)	0.086 (2)	0.0581 (19)	−0.0022 (18)	0.0048 (16)	0.0225 (18)
N21	0.0538 (16)	0.0554 (18)	0.0638 (19)	0.0009 (14)	0.0170 (14)	0.0003 (14)
N22	0.0461 (16)	0.0449 (16)	0.0673 (18)	0.0076 (14)	0.0020 (13)	−0.0047 (14)
N23	0.075 (2)	0.0576 (19)	0.0566 (18)	0.0019 (16)	−0.0021 (15)	−0.0104 (16)
O11	0.0609 (15)	0.0339 (13)	0.0823 (16)	0.0000 (11)	0.0032 (12)	0.0073 (11)
O12	0.109 (2)	0.0684 (19)	0.097 (2)	−0.0074 (17)	0.0045 (16)	−0.0275 (16)
O21	0.0570 (14)	0.0326 (13)	0.0865 (16)	−0.0010 (11)	0.0034 (12)	0.0032 (12)
O22	0.176 (3)	0.0384 (16)	0.116 (2)	0.0001 (17)	−0.008 (2)	0.0204 (15)

Geometric parameters (Å, º)

C2—N11	1.457 (3)	C22—C23	1.497 (5)
C2—C3	1.491 (4)	C22—H22A	0.9700
C2—H2A	0.9700	C22—H22B	0.9700
C2—H2B	0.9700	C23—C24	1.538 (4)
C3—C4	1.545 (4)	C23—H23A	0.9700
C3—H3A	0.9700	C23—H23B	0.9700
C3—H3B	0.9700	C24—C34	1.529 (4)
C4—C17	1.529 (4)	C24—C37	1.532 (4)
C4—C14	1.545 (4)	C24—C25	1.573 (4)
C4—C5	1.580 (4)	C25—N21	1.469 (3)
C5—N11	1.464 (3)	C25—C27	1.514 (4)
C5—C7	1.521 (4)	C25—C33	1.543 (4)
C5—C13	1.557 (4)	C26—N21	1.460 (4)
C6—N11	1.464 (3)	C26—H26A	0.9600
C6—H6A	0.9600	C26—H26B	0.9600
C6—H6B	0.9600	C26—H26C	0.9600
C6—H6C	0.9600	C27—C28	1.383 (4)
C7—C12	1.385 (4)	C27—C32	1.392 (4)
C7—C8	1.387 (4)	C28—C29	1.387 (5)
C8—C9	1.388 (4)	C28—H28	0.9300
C8—H8	0.9300	C29—C30	1.369 (5)
C9—C10	1.372 (4)	C29—H29	0.9300
C9—H9	0.9300	C30—C31	1.389 (5)
C10—C11	1.386 (4)	C30—H30	0.9300
C10—H10	0.9300	C31—C32	1.376 (4)
C11—C12	1.378 (4)	C31—H31	0.9300
C11—H11	0.9300	C32—N22	1.403 (4)
C12—N12	1.401 (3)	C33—O21	1.214 (3)
C13—O11	1.214 (3)	C33—N22	1.361 (3)
C13—N12	1.360 (3)	C34—O22	1.207 (4)
C14—O12	1.205 (4)	C34—C35	1.495 (5)
C14—C15	1.493 (5)	C35—C36	1.518 (5)
C15—C16	1.512 (5)	C35—H35A	0.9700
C15—H15A	0.9700	C35—H35B	0.9700
C15—H15B	0.9700	C36—N23	1.446 (4)
C16—N13	1.459 (4)	C36—H36A	0.9700
C16—H16A	0.9700	C36—H36B	0.9700
C16—H16B	0.9700	C37—N23	1.443 (4)
C17—N13	1.442 (4)	C37—H37A	0.9700
C17—H17A	0.9700	C37—H37B	0.9700
C17—H17B	0.9700	C38—N23	1.458 (4)
C18—N13	1.453 (4)	C38—H38A	0.9600
C18—H18A	0.9600	C38—H38B	0.9600
C18—H18B	0.9600	C38—H38C	0.9600
C18—H18C	0.9600	N12—H12	0.8600
C22—N21	1.465 (4)	N22—H22	0.8600
N11—C2—C3	102.9 (2)	C22—C23—H23B	110.2
N11—C2—H2A	111.2	C24—C23—H23B	110.2
C3—C2—H2A	111.2	H23A—C23—H23B	108.5
N11—C2—H2B	111.2	C34—C24—C37	105.2 (3)
C3—C2—H2B	111.2	C34—C24—C23	113.1 (3)
H2A—C2—H2B	109.1	C37—C24—C23	109.6 (3)
C2—C3—C4	107.1 (2)	C34—C24—C25	112.8 (3)
C2—C3—H3A	110.3	C37—C24—C25	113.3 (2)
C4—C3—H3A	110.3	C23—C24—C25	102.9 (3)
C2—C3—H3B	110.3	N21—C25—C27	118.2 (2)
C4—C3—H3B	110.3	N21—C25—C33	105.6 (2)
H3A—C3—H3B	108.5	C27—C25—C33	101.8 (2)
C17—C4—C14	106.1 (2)	N21—C25—C24	101.9 (2)
C17—C4—C3	111.4 (3)	C27—C25—C24	113.1 (2)
C14—C4—C3	112.1 (3)	C33—C25—C24	116.7 (2)
C17—C4—C5	111.5 (2)	N21—C26—H26A	109.5
C14—C4—C5	112.9 (2)	N21—C26—H26B	109.5
C3—C4—C5	103.0 (2)	H26A—C26—H26B	109.5
N11—C5—C7	119.1 (2)	N21—C26—H26C	109.5
N11—C5—C13	105.8 (2)	H26A—C26—H26C	109.5
C7—C5—C13	100.9 (2)	H26B—C26—H26C	109.5
N11—C5—C4	102.1 (2)	C28—C27—C32	118.9 (3)
C7—C5—C4	112.7 (2)	C28—C27—C25	132.2 (3)
C13—C5—C4	116.8 (2)	C32—C27—C25	108.8 (3)
N11—C6—H6A	109.5	C27—C28—C29	118.9 (3)
N11—C6—H6B	109.5	C27—C28—H28	120.6
H6A—C6—H6B	109.5	C29—C28—H28	120.6
N11—C6—H6C	109.5	C30—C29—C28	120.8 (4)
H6A—C6—H6C	109.5	C30—C29—H29	119.6
H6B—C6—H6C	109.5	C28—C29—H29	119.6
C12—C7—C8	119.1 (3)	C29—C30—C31	122.0 (4)
C12—C7—C5	109.0 (2)	C29—C30—H30	119.0
C8—C7—C5	131.6 (3)	C31—C30—H30	119.0
C7—C8—C9	119.3 (3)	C32—C31—C30	116.3 (4)
C7—C8—H8	120.4	C32—C31—H31	121.8
C9—C8—H8	120.4	C30—C31—H31	121.8
C10—C9—C8	120.4 (3)	C31—C32—C27	123.2 (3)
C10—C9—H9	119.8	C31—C32—N22	127.5 (3)
C8—C9—H9	119.8	C27—C32—N22	109.4 (3)
C9—C10—C11	121.4 (3)	O21—C33—N22	126.1 (3)
C9—C10—H10	119.3	O21—C33—C25	125.8 (3)
C11—C10—H10	119.3	N22—C33—C25	107.8 (2)
C12—C11—C10	117.5 (3)	O22—C34—C35	121.9 (4)
C12—C11—H11	121.3	O22—C34—C24	122.5 (4)
C10—C11—H11	121.3	C35—C34—C24	115.2 (3)
C11—C12—C7	122.3 (3)	C34—C35—C36	109.1 (3)
C11—C12—N12	127.7 (3)	C34—C35—H35A	109.9
C7—C12—N12	109.9 (3)	C36—C35—H35A	109.9
O11—C13—N12	126.3 (3)	C34—C35—H35B	109.9
O11—C13—C5	125.2 (3)	C36—C35—H35B	109.9
N12—C13—C5	108.1 (2)	H35A—C35—H35B	108.3
O12—C14—C15	121.8 (3)	N23—C36—C35	108.6 (3)
O12—C14—C4	121.9 (3)	N23—C36—H36A	110.0
C15—C14—C4	116.0 (3)	C35—C36—H36A	110.0
C14—C15—C16	111.2 (3)	N23—C36—H36B	110.0
C14—C15—H15A	109.4	C35—C36—H36B	110.0
C16—C15—H15A	109.4	H36A—C36—H36B	108.4
C14—C15—H15B	109.4	N23—C37—C24	113.6 (3)
C16—C15—H15B	109.4	N23—C37—H37A	108.9
H15A—C15—H15B	108.0	C24—C37—H37A	108.9
N13—C16—C15	109.2 (3)	N23—C37—H37B	108.9
N13—C16—H16A	109.8	C24—C37—H37B	108.9
C15—C16—H16A	109.8	H37A—C37—H37B	107.7
N13—C16—H16B	109.8	N23—C38—H38A	109.5
C15—C16—H16B	109.8	N23—C38—H38B	109.5
H16A—C16—H16B	108.3	H38A—C38—H38B	109.5
N13—C17—C4	111.2 (3)	N23—C38—H38C	109.5
N13—C17—H17A	109.4	H38A—C38—H38C	109.5
C4—C17—H17A	109.4	H38B—C38—H38C	109.5
N13—C17—H17B	109.4	C2—N11—C5	106.7 (2)
C4—C17—H17B	109.4	C2—N11—C6	115.0 (2)
H17A—C17—H17B	108.0	C5—N11—C6	115.2 (2)
N13—C18—H18A	109.5	C13—N12—C12	111.6 (2)
N13—C18—H18B	109.5	C13—N12—H12	124.2
H18A—C18—H18B	109.5	C12—N12—H12	124.2
N13—C18—H18C	109.5	C17—N13—C18	111.8 (3)
H18A—C18—H18C	109.5	C17—N13—C16	111.2 (3)
H18B—C18—H18C	109.5	C18—N13—C16	113.3 (3)
N21—C22—C23	103.3 (3)	C26—N21—C22	114.1 (3)
N21—C22—H22A	111.1	C26—N21—C25	115.5 (2)
C23—C22—H22A	111.1	C22—N21—C25	106.4 (2)
N21—C22—H22B	111.1	C33—N22—C32	111.8 (3)
C23—C22—H22B	111.1	C33—N22—H22	124.1
H22A—C22—H22B	109.1	C32—N22—H22	124.1
C22—C23—C24	107.7 (3)	C37—N23—C36	111.2 (3)
C22—C23—H23A	110.2	C37—N23—C38	110.6 (3)
C24—C23—H23A	110.2	C36—N23—C38	112.9 (3)
N11—C2—C3—C4	−26.6 (3)	N21—C25—C27—C32	−120.4 (3)
C2—C3—C4—C17	122.1 (3)	C33—C25—C27—C32	−5.3 (3)
C2—C3—C4—C14	−119.2 (3)	C24—C25—C27—C32	120.7 (3)
C2—C3—C4—C5	2.4 (3)	C32—C27—C28—C29	0.6 (5)
C17—C4—C5—N11	−97.2 (3)	C25—C27—C28—C29	177.0 (3)
C14—C4—C5—N11	143.5 (3)	C27—C28—C29—C30	−1.1 (6)
C3—C4—C5—N11	22.4 (3)	C28—C29—C30—C31	1.1 (6)
C17—C4—C5—C7	133.9 (3)	C29—C30—C31—C32	−0.5 (6)
C14—C4—C5—C7	14.5 (3)	C30—C31—C32—C27	0.1 (5)
C3—C4—C5—C7	−106.6 (3)	C30—C31—C32—N22	−179.4 (3)
C17—C4—C5—C13	17.6 (3)	C28—C27—C32—C31	−0.1 (5)
C14—C4—C5—C13	−101.7 (3)	C25—C27—C32—C31	−177.3 (3)
C3—C4—C5—C13	137.2 (3)	C28—C27—C32—N22	179.4 (3)
N11—C5—C7—C12	121.5 (3)	C25—C27—C32—N22	2.3 (3)
C13—C5—C7—C12	6.4 (3)	N21—C25—C33—O21	−43.6 (4)
C4—C5—C7—C12	−119.0 (3)	C27—C25—C33—O21	−167.7 (3)
N11—C5—C7—C8	−64.6 (4)	C24—C25—C33—O21	68.7 (4)
C13—C5—C7—C8	−179.7 (3)	N21—C25—C33—N22	130.6 (2)
C4—C5—C7—C8	54.9 (4)	C27—C25—C33—N22	6.6 (3)
C12—C7—C8—C9	1.4 (5)	C24—C25—C33—N22	−117.1 (3)
C5—C7—C8—C9	−172.0 (3)	C37—C24—C34—O22	−122.8 (4)
C7—C8—C9—C10	0.4 (5)	C23—C24—C34—O22	−3.1 (5)
C8—C9—C10—C11	−1.4 (6)	C25—C24—C34—O22	113.2 (4)
C9—C10—C11—C12	0.5 (5)	C37—C24—C34—C35	51.2 (4)
C10—C11—C12—C7	1.4 (5)	C23—C24—C34—C35	170.9 (3)
C10—C11—C12—N12	178.5 (3)	C25—C24—C34—C35	−72.8 (4)
C8—C7—C12—C11	−2.3 (5)	O22—C34—C35—C36	118.6 (4)
C5—C7—C12—C11	172.4 (3)	C24—C34—C35—C36	−55.5 (4)
C8—C7—C12—N12	−179.9 (3)	C34—C35—C36—N23	57.9 (4)
C5—C7—C12—N12	−5.2 (3)	C34—C24—C37—N23	−53.5 (3)
N11—C5—C13—O11	42.6 (4)	C23—C24—C37—N23	−175.5 (3)
C7—C5—C13—O11	167.3 (3)	C25—C24—C37—N23	70.2 (3)
C4—C5—C13—O11	−70.1 (4)	C3—C2—N11—C5	43.0 (3)
N11—C5—C13—N12	−130.3 (2)	C3—C2—N11—C6	172.0 (2)
C7—C5—C13—N12	−5.6 (3)	C7—C5—N11—C2	84.0 (3)
C4—C5—C13—N12	117.0 (3)	C13—C5—N11—C2	−163.5 (2)
C17—C4—C14—O12	125.6 (3)	C4—C5—N11—C2	−40.9 (3)
C3—C4—C14—O12	3.9 (4)	C7—C5—N11—C6	−45.0 (3)
C5—C4—C14—O12	−111.9 (3)	C13—C5—N11—C6	67.5 (3)
C17—C4—C14—C15	−48.7 (4)	C4—C5—N11—C6	−169.8 (2)
C3—C4—C14—C15	−170.5 (3)	O11—C13—N12—C12	−169.8 (3)
C5—C4—C14—C15	73.7 (3)	C5—C13—N12—C12	3.0 (3)
O12—C14—C15—C16	−125.6 (4)	C11—C12—N12—C13	−176.1 (3)
C4—C14—C15—C16	48.8 (4)	C7—C12—N12—C13	1.3 (3)
C14—C15—C16—N13	−52.7 (4)	C4—C17—N13—C18	165.5 (3)
C14—C4—C17—N13	56.0 (3)	C4—C17—N13—C16	−66.7 (4)
C3—C4—C17—N13	178.2 (3)	C15—C16—N13—C17	62.9 (4)
C5—C4—C17—N13	−67.4 (3)	C15—C16—N13—C18	−170.2 (3)
N21—C22—C23—C24	21.2 (4)	C23—C22—N21—C26	−168.8 (3)
C22—C23—C24—C34	125.7 (3)	C23—C22—N21—C25	−40.2 (3)
C22—C23—C24—C37	−117.1 (3)	C27—C25—N21—C26	45.3 (4)
C22—C23—C24—C25	3.7 (4)	C33—C25—N21—C26	−67.7 (3)
C34—C24—C25—N21	−149.2 (3)	C24—C25—N21—C26	169.9 (3)
C37—C24—C25—N21	91.3 (3)	C27—C25—N21—C22	−82.4 (3)
C23—C24—C25—N21	−27.0 (3)	C33—C25—N21—C22	164.6 (2)
C34—C24—C25—C27	−21.3 (3)	C24—C25—N21—C22	42.2 (3)
C37—C24—C25—C27	−140.7 (3)	O21—C33—N22—C32	168.5 (3)
C23—C24—C25—C27	101.0 (3)	C25—C33—N22—C32	−5.8 (3)
C34—C24—C25—C33	96.3 (3)	C31—C32—N22—C33	−178.2 (3)
C37—C24—C25—C33	−23.1 (4)	C27—C32—N22—C33	2.3 (3)
C23—C24—C25—C33	−141.4 (3)	C24—C37—N23—C36	62.9 (3)
N21—C25—C27—C28	63.0 (4)	C24—C37—N23—C38	−170.8 (3)
C33—C25—C27—C28	178.1 (3)	C35—C36—N23—C37	−62.6 (4)
C24—C25—C27—C28	−55.9 (4)	C35—C36—N23—C38	172.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N22—H22···O11^i	0.86	2.49	3.144 (3)	133
N22—H22···N11^i	0.86	2.27	3.066 (3)	153
N12—H12···O21	0.86	2.30	3.008 (3)	140
N12—H12···N21	0.86	2.47	3.198 (3)	143
C11—H11···O21	0.93	2.44	3.173 (4)	136

Symmetry code: (i) x−1, y, z.