3-Benzyl­idene-1′-methyl-4′-phenyl­cyclo­hexane­spiro-3′-pyrrolidine-2′-spiro-3′′-indoline-2,2′′-dione

In the title compound, C₃₀H₂₈N₂O₂, there are two mol­ecules in the asymmetric unit. In both mol­ecules, the pyrrolidine ring adopts an envelope conformation whereas the conformation of the cyclo­hexane ring is half-chair. The ox­indole moiety is almost perpendicular to the pyrrolidine ring; the benzyl­idene moiety and the phenyl ring are in equatorial and bisectional configurations with respect to their attached pyrrolidine and cyclo­hexanone rings, respectively. Intramolecular C—H...O and intermolecular N—H...N and N—H...O interactions stabilize the molecular structure and the packing in the crystal.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.057
• wR factor = 0.141
• Data-to-parameter ratio = 13.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

Substituted pyrrolidine compounds have gained much importance since they are the basic structural elements of many alkaloids and pharmacologically active compounds, while molecules with indole moiety possess anti-inflammatory and antibacterial properties. Our interest on preparing the pharmacologically active pyrrolidine compounds led us to the title compound, (I), and we have undertaken an X-ray crystal structure determination of (I) in order to establish the conformation of the structure.

In the title structure, the asymmetric unit contains an enantiomeric pair of molecules (A and B) with almost identical geometry, except for the rotation of the phenyl rings about the C12—C13 bond. In the two molecules, the bond lengths and angles show normal values (Allen et al., 1987) and agree with each other. The values within the oxindole moiety are slightly different compared with those of the indole derivative (Zukerman-Schpector, 1992), especially with regard to the longer C1—C8 and C7—C8 bond lengths, due to the spiro-atom character and the steric effect of the bulky group substituted at C8. The arguments can also be applied to the longer C—C and C—N bond lengths within the pyrrolidine ring, while the N1 atom is in a pyramidal configuration (Perales et al., 1977), compared with those of the pyrrolidine ring in a previous study (Gzella & Wrzeciono, 1990). The average C—C bond distance in the cyclohexane ring is 1.520 (4) Å in the two molecules.

In both molecules A and B, the pyrrolidine ring adopts an envelope conformation and the cyclohexane ring is in a half-chair conformation, with a dihedral angle between them of 84.3 (1)° in molecule A and 85.3 (1)° in molecule B. The conformations were confirmed by their puckering parameters (Cremer & Pople, 1975); for the pyrrolidine ring Q₂ = 0.420 (3) Å and ϕ₂ = 187.4 (4)° in molecule A and Q₂ = 0.405 (3) Å and ϕ₂ = 0.7 (4)° in molecule B, while for the cyclohexane ring, Q₂ = 0.281 (3), Q₃ = 0.403 (3), Q_T = 0.491 (3) Å and ϕ₂ = 258.6 (6)° in molecule A, and Q₂ = 0.311 (3), Q₃ = -0.381 (3), Q_T = 0.492 (3) Å and ϕ₂ = 93.1 (5)° in molecule B. The phenyl ring attached at C23 is in a bisectional configuration with respect to the pyrrolidine ring in both molecules, corresponding to a dihedral angle between the phenyl and pyrrolidine rings of 83.6 (2)° in molecule A and 81.4 (2)° in molecule B. The phenyl ring attached at C12 makes dihedral angles of 63.2 (2) and 46.2 (2)° with the cyclohexane ring in molecules A and B, respectively. In the oxindole moiety, the phenyl and pyrrole rings are individually planar and make a dihedral angle of 4.1 (2) and 4.2 (2)° in molecule A and B, respectively, while the attached O2A and O2B atoms deviate by -0.204 (2) and 0.171 (2) Å, respectively, from the mean planes of the oxindole moieties in the two molecules. The oxindole moiety makes dihedral angles of 89.9 (1) and 87.8 (1)° with the pyrrolidine ring in molecules A and B, respectively, corresponding to nearly perpendicular configurations.

The closest distances of C12···O1 and C23···O1 are within 2.764 (3) Å (Table 2), implying intramolecular non-bonded hydrogen interactions and forming closed O1—C10—C11—C12—H12 and O1—C10—C9—C23—H23 rings. These interactions stabilize the molecular structure, while the observed intermolecular N—H···N and N—H···O (Table 2) interactions interconnecting molecules A and B in different asymmetric units, as well as van der Waals interactions, stabilize the crystal structure.

S2. Experimental

A mixture of 2,6-dibenzylidenecyclohexanone (1 mmol), sarcosine (1 mmol) and isotin (1 mmol) in methanol was refluxed for 4 h. After the reaction, the solvent was evaporated in vacuo and the resulting crude product was purified by column chromatography using a hexane–ethyl acetate mixture (9:1). Slow evaporation of the isolated compound from ethanol solution gave light-yellow single crystals suitable for X-ray structure determination.

S3. Refinement

After checking their presence in the difference map, all H atoms were fixed geometrically and allowed to ride on the parent C atoms and refined isotropically. Due to large fraction of weak data at higher angles, the 2θ maximum was limited to 50°.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures

Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids

4-Benzylidene-1'-methyl-4'-phenylcyclohexanespiro-3'-pyrrolidine-2'-spiro- 3''-indoline-2,2''-dione

Crystal data

C30H28N2O2	Z = 4
Mr = 448.54	F(000) = 952
Triclinic, P1	Dx = 1.249 Mg m^−3
a = 12.3624 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.0640 (2) Å	Cell parameters from 6647 reflections
c = 17.1439 (3) Å	θ = 1.3–29.5°
α = 110.066 (1)°	µ = 0.08 mm^−1
β = 93.200 (1)°	T = 293 K
γ = 110.534 (1)°	Slab, light yellow
V = 2386.13 (6) Å^3	0.36 × 0.24 × 0.16 mm

Data collection

Siemens SMART CCD area-detector diffractometer	8228 independent reflections
Radiation source: fine-focus sealed tube	4402 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 1.3°
ω scans	h = −14→14
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −15→9
Tmin = 0.972, Tmax = 0.988	l = −20→20
13509 measured reflections

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)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.141	w = 1/[σ^2(Fo^2) + (0.0379P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.88	(Δ/σ)max < 0.001
8228 reflections	Δρmax = 0.23 e Å^−3
616 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (1)

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
O1A	0.02652 (14)	0.41605 (15)	0.06499 (11)	0.0461 (5)
O2A	0.32236 (16)	0.21054 (17)	0.08694 (12)	0.0547 (5)
N1A	0.08413 (17)	0.23158 (18)	0.10979 (13)	0.0398 (5)
N2A	0.37296 (18)	0.35678 (19)	0.21900 (14)	0.0442 (6)
H2AA	0.4382	0.3536	0.2357	0.053*
C1A	0.3044 (2)	0.2888 (2)	0.14034 (17)	0.0401 (6)
C2A	0.3252 (2)	0.4322 (2)	0.26958 (16)	0.0378 (6)
C3A	0.3661 (2)	0.5065 (2)	0.35383 (17)	0.0484 (7)
H3AA	0.4355	0.5145	0.3839	0.058*
C4A	0.3006 (2)	0.5689 (3)	0.39223 (18)	0.0545 (8)
H4AA	0.3260	0.6193	0.4492	0.065*
C5A	0.1982 (2)	0.5576 (2)	0.34740 (17)	0.0520 (7)
H5AA	0.1559	0.6010	0.3743	0.062*
C6A	0.1574 (2)	0.4822 (2)	0.26270 (16)	0.0432 (7)
H6AA	0.0869	0.4733	0.2334	0.052*
C7A	0.2226 (2)	0.4204 (2)	0.22224 (15)	0.0354 (6)
C8A	0.1997 (2)	0.3288 (2)	0.13273 (15)	0.0358 (6)
C9A	0.1964 (2)	0.3686 (2)	0.05471 (15)	0.0342 (6)
C10A	0.1344 (2)	0.4552 (2)	0.07441 (15)	0.0364 (6)
C11A	0.2018 (2)	0.5859 (2)	0.10707 (16)	0.0382 (6)
C12A	0.1464 (2)	0.6528 (2)	0.14777 (17)	0.0461 (7)
H12A	0.0716	0.6123	0.1550	0.055*
C13A	0.1891 (2)	0.7826 (2)	0.18259 (18)	0.0439 (7)
C14A	0.1755 (3)	0.8422 (3)	0.2631 (2)	0.0660 (9)
H14A	0.1423	0.8003	0.2959	0.079*
C15A	0.2114 (3)	0.9641 (3)	0.2946 (2)	0.0829 (11)
H15A	0.2049	1.0038	0.3496	0.100*
C16A	0.2562 (3)	1.0274 (3)	0.2465 (3)	0.0780 (11)
H16A	0.2791	1.1092	0.2682	0.094*
C17A	0.2668 (3)	0.9693 (3)	0.1668 (2)	0.0691 (9)
H17A	0.2966	1.0115	0.1334	0.083*
C18A	0.2339 (2)	0.8490 (3)	0.1353 (2)	0.0572 (8)
H18A	0.2420	0.8108	0.0805	0.069*
C19A	0.3276 (2)	0.6338 (2)	0.09533 (18)	0.0468 (7)
H19A	0.3703	0.7121	0.1393	0.056*
H19B	0.3277	0.6413	0.0410	0.056*
C20A	0.3896 (2)	0.5531 (2)	0.09918 (17)	0.0460 (7)
H20A	0.4674	0.5821	0.0865	0.055*
H20B	0.3989	0.5535	0.1559	0.055*
C21A	0.3182 (2)	0.4273 (2)	0.03562 (16)	0.0415 (6)
H21A	0.3629	0.3791	0.0348	0.050*
H21B	0.3071	0.4287	−0.0204	0.050*
C22A	0.0673 (2)	0.1593 (2)	0.01987 (16)	0.0459 (7)
H22A	−0.0153	0.1087	−0.0040	0.055*
H22B	0.1124	0.1102	0.0116	0.055*
C23A	0.1123 (2)	0.2505 (2)	−0.02084 (15)	0.0391 (6)
H23A	0.0439	0.2651	−0.0377	0.047*
C24A	0.1572 (2)	0.2070 (2)	−0.10116 (16)	0.0418 (6)
C25A	0.2342 (3)	0.1518 (3)	−0.1091 (2)	0.0780 (11)
H25A	0.2631	0.1410	−0.0626	0.094*
C26A	0.2701 (3)	0.1117 (4)	−0.1849 (2)	0.0933 (13)
H26A	0.3240	0.0762	−0.1882	0.112*
C27A	0.2271 (3)	0.1236 (3)	−0.2545 (2)	0.0699 (9)
H27A	0.2498	0.0949	−0.3057	0.084*
C28A	0.1515 (3)	0.1773 (3)	−0.2486 (2)	0.0677 (9)
H28A	0.1226	0.1866	−0.2958	0.081*
C29A	0.1158 (3)	0.2193 (3)	−0.17249 (18)	0.0566 (8)
H29A	0.0632	0.2562	−0.1697	0.068*
C30A	0.0628 (2)	0.1629 (2)	0.16399 (18)	0.0577 (8)
H30A	−0.0153	0.1018	0.1441	0.087*
H30B	0.0703	0.2147	0.2213	0.087*
H30C	0.1194	0.1277	0.1619	0.087*
O1B	0.45692 (15)	0.68176 (16)	−0.35926 (12)	0.0550 (5)
O2B	0.09725 (16)	0.47035 (19)	−0.23569 (13)	0.0621 (6)
N1B	0.36504 (17)	0.57416 (19)	−0.22434 (13)	0.0403 (5)
N2B	0.15068 (19)	0.6668 (2)	−0.15352 (15)	0.0578 (7)
H2BA	0.0910	0.6599	−0.1292	0.069*
C1B	0.1634 (2)	0.5749 (3)	−0.21241 (18)	0.0472 (7)
C2B	0.2448 (2)	0.7747 (3)	−0.13596 (17)	0.0469 (7)
C3B	0.2640 (3)	0.8842 (3)	−0.07577 (18)	0.0590 (8)
H3BA	0.2087	0.8949	−0.0427	0.071*
C4B	0.3676 (3)	0.9776 (3)	−0.06591 (18)	0.0607 (8)
H4BA	0.3824	1.0526	−0.0258	0.073*
C5B	0.4495 (3)	0.9614 (3)	−0.11463 (18)	0.0560 (8)
H5BA	0.5192	1.0255	−0.1069	0.067*
C6B	0.4291 (2)	0.8499 (2)	−0.17558 (17)	0.0457 (7)
H6BA	0.4851	0.8394	−0.2081	0.055*
C7B	0.3258 (2)	0.7556 (2)	−0.18725 (16)	0.0398 (6)
C8B	0.2817 (2)	0.6244 (2)	−0.24240 (16)	0.0372 (6)
C9B	0.2616 (2)	0.5809 (2)	−0.34267 (15)	0.0359 (6)
C10B	0.3567 (2)	0.6788 (2)	−0.36207 (15)	0.0377 (6)
C11B	0.3277 (2)	0.7701 (2)	−0.38115 (15)	0.0394 (6)
C12B	0.4188 (2)	0.8669 (2)	−0.37696 (17)	0.0486 (7)
H12B	0.4930	0.8680	−0.3627	0.058*
C13B	0.4189 (2)	0.9712 (3)	−0.39142 (18)	0.0496 (7)
C14B	0.5052 (3)	1.0820 (3)	−0.3403 (2)	0.0659 (9)
H14B	0.5603	1.0876	−0.2982	0.079*
C15B	0.5104 (3)	1.1826 (3)	−0.3510 (2)	0.0809 (11)
H15B	0.5683	1.2557	−0.3158	0.097*
C16B	0.4308 (4)	1.1766 (3)	−0.4131 (2)	0.0800 (11)
H16B	0.4343	1.2452	−0.4199	0.096*
C17B	0.3464 (4)	1.0689 (4)	−0.4648 (2)	0.0860 (12)
H17B	0.2922	1.0641	−0.5072	0.103*
C18B	0.3409 (3)	0.9663 (3)	−0.4544 (2)	0.0726 (10)
H18B	0.2837	0.8934	−0.4905	0.087*
C19B	0.2002 (2)	0.7536 (2)	−0.40103 (18)	0.0517 (7)
H19C	0.1736	0.7201	−0.4621	0.062*
H19D	0.1954	0.8305	−0.3790	0.062*
C20B	0.1183 (2)	0.6735 (2)	−0.36403 (18)	0.0488 (7)
H20C	0.1323	0.7144	−0.3030	0.059*
H20D	0.0370	0.6545	−0.3871	0.059*
C21B	0.1391 (2)	0.5605 (2)	−0.38484 (17)	0.0442 (7)
H21C	0.1295	0.5228	−0.4458	0.053*
H21D	0.0798	0.5067	−0.3668	0.053*
C22B	0.3241 (2)	0.4534 (2)	−0.28920 (17)	0.0485 (7)
H22C	0.2565	0.3997	−0.2772	0.058*
H22D	0.3863	0.4238	−0.2927	0.058*
C23B	0.2908 (2)	0.4673 (2)	−0.37090 (16)	0.0428 (7)
H23B	0.3629	0.4872	−0.3937	0.051*
C24B	0.2004 (3)	0.3555 (2)	−0.43926 (19)	0.0546 (8)
C25B	0.0983 (3)	0.2829 (3)	−0.4228 (2)	0.0764 (10)
H25B	0.0828	0.3038	−0.3683	0.092*
C26B	0.0200 (4)	0.1796 (3)	−0.4878 (4)	0.1114 (17)
H26B	−0.0478	0.1322	−0.4762	0.134*
C27B	0.0404 (6)	0.1467 (4)	−0.5677 (4)	0.132 (3)
H27B	−0.0115	0.0761	−0.6102	0.159*
C28B	0.1381 (5)	0.2182 (4)	−0.5849 (3)	0.1121 (18)
H28B	0.1507	0.1984	−0.6401	0.134*
C29B	0.2184 (4)	0.3200 (3)	−0.5210 (2)	0.0799 (11)
H29B	0.2863	0.3656	−0.5336	0.096*
C30B	0.3810 (2)	0.5784 (3)	−0.13740 (17)	0.0584 (8)
H30D	0.4101	0.6594	−0.0978	0.088*
H30E	0.4365	0.5446	−0.1304	0.088*
H30F	0.3067	0.5342	−0.1273	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0357 (10)	0.0480 (11)	0.0594 (13)	0.0192 (9)	0.0180 (9)	0.0222 (10)
O2A	0.0665 (13)	0.0529 (12)	0.0523 (13)	0.0386 (11)	0.0132 (10)	0.0134 (10)
N1A	0.0393 (12)	0.0354 (12)	0.0387 (13)	0.0076 (10)	0.0085 (10)	0.0146 (11)
N2A	0.0376 (12)	0.0519 (14)	0.0451 (15)	0.0227 (11)	0.0038 (11)	0.0167 (12)
C1A	0.0426 (15)	0.0395 (16)	0.0433 (18)	0.0186 (13)	0.0138 (13)	0.0187 (14)
C2A	0.0349 (14)	0.0377 (15)	0.0400 (16)	0.0116 (12)	0.0094 (12)	0.0167 (13)
C3A	0.0418 (15)	0.0555 (18)	0.0401 (18)	0.0135 (14)	0.0038 (13)	0.0160 (15)
C4A	0.0544 (18)	0.061 (2)	0.0346 (17)	0.0168 (16)	0.0090 (14)	0.0096 (15)
C5A	0.0518 (17)	0.0585 (19)	0.0444 (19)	0.0256 (15)	0.0190 (15)	0.0129 (15)
C6A	0.0374 (14)	0.0483 (17)	0.0390 (17)	0.0161 (13)	0.0109 (12)	0.0114 (14)
C7A	0.0369 (14)	0.0349 (15)	0.0352 (15)	0.0128 (12)	0.0092 (12)	0.0157 (12)
C8A	0.0360 (14)	0.0328 (14)	0.0390 (16)	0.0152 (12)	0.0068 (12)	0.0129 (12)
C9A	0.0340 (13)	0.0345 (14)	0.0378 (15)	0.0145 (12)	0.0107 (11)	0.0168 (12)
C10A	0.0347 (15)	0.0423 (16)	0.0376 (16)	0.0156 (13)	0.0136 (12)	0.0202 (13)
C11A	0.0351 (14)	0.0397 (15)	0.0456 (17)	0.0161 (13)	0.0127 (12)	0.0213 (13)
C12A	0.0394 (15)	0.0458 (17)	0.060 (2)	0.0211 (14)	0.0188 (14)	0.0231 (15)
C13A	0.0389 (15)	0.0416 (16)	0.0579 (19)	0.0227 (13)	0.0132 (13)	0.0192 (15)
C14A	0.087 (2)	0.064 (2)	0.058 (2)	0.047 (2)	0.0175 (18)	0.0187 (18)
C15A	0.114 (3)	0.070 (3)	0.060 (2)	0.057 (2)	0.003 (2)	0.000 (2)
C16A	0.073 (2)	0.046 (2)	0.104 (3)	0.0297 (19)	−0.004 (2)	0.013 (2)
C17A	0.064 (2)	0.050 (2)	0.102 (3)	0.0253 (18)	0.024 (2)	0.035 (2)
C18A	0.0587 (18)	0.0441 (19)	0.078 (2)	0.0270 (15)	0.0259 (16)	0.0247 (17)
C19A	0.0403 (15)	0.0425 (16)	0.0585 (19)	0.0136 (13)	0.0200 (13)	0.0221 (14)
C20A	0.0325 (14)	0.0510 (18)	0.0612 (19)	0.0177 (13)	0.0221 (13)	0.0264 (15)
C21A	0.0378 (14)	0.0497 (17)	0.0477 (17)	0.0244 (13)	0.0196 (12)	0.0222 (14)
C22A	0.0486 (16)	0.0373 (16)	0.0424 (17)	0.0142 (13)	0.0083 (13)	0.0074 (13)
C23A	0.0402 (14)	0.0391 (15)	0.0398 (16)	0.0201 (13)	0.0064 (12)	0.0131 (13)
C24A	0.0482 (16)	0.0395 (16)	0.0383 (17)	0.0200 (14)	0.0079 (13)	0.0131 (13)
C25A	0.116 (3)	0.113 (3)	0.047 (2)	0.089 (3)	0.029 (2)	0.034 (2)
C26A	0.133 (3)	0.139 (4)	0.062 (2)	0.109 (3)	0.045 (2)	0.040 (2)
C27A	0.095 (3)	0.075 (2)	0.046 (2)	0.042 (2)	0.0287 (18)	0.0192 (18)
C28A	0.091 (2)	0.073 (2)	0.044 (2)	0.035 (2)	0.0124 (18)	0.0249 (17)
C29A	0.0629 (19)	0.064 (2)	0.0471 (19)	0.0336 (17)	0.0060 (15)	0.0184 (16)
C30A	0.0617 (19)	0.0474 (18)	0.063 (2)	0.0102 (15)	0.0142 (15)	0.0311 (16)
O1B	0.0421 (11)	0.0569 (13)	0.0789 (15)	0.0238 (10)	0.0261 (10)	0.0349 (11)
O2B	0.0424 (11)	0.0655 (14)	0.0795 (16)	0.0121 (11)	0.0237 (10)	0.0370 (12)
N1B	0.0355 (12)	0.0500 (14)	0.0385 (13)	0.0180 (11)	0.0070 (10)	0.0197 (11)
N2B	0.0420 (14)	0.0776 (18)	0.0563 (17)	0.0257 (14)	0.0289 (12)	0.0236 (14)
C1B	0.0312 (15)	0.063 (2)	0.0534 (19)	0.0171 (15)	0.0151 (13)	0.0307 (17)
C2B	0.0384 (15)	0.063 (2)	0.0407 (17)	0.0238 (15)	0.0094 (13)	0.0185 (15)
C3B	0.060 (2)	0.082 (2)	0.0449 (19)	0.0452 (19)	0.0188 (15)	0.0160 (18)
C4B	0.068 (2)	0.063 (2)	0.047 (2)	0.0404 (19)	0.0030 (16)	0.0030 (16)
C5B	0.0540 (18)	0.0525 (19)	0.052 (2)	0.0214 (15)	0.0026 (15)	0.0103 (16)
C6B	0.0414 (15)	0.0500 (18)	0.0415 (17)	0.0173 (14)	0.0119 (13)	0.0133 (14)
C7B	0.0398 (15)	0.0496 (17)	0.0335 (15)	0.0232 (14)	0.0097 (12)	0.0141 (13)
C8B	0.0304 (13)	0.0458 (16)	0.0397 (16)	0.0167 (12)	0.0126 (11)	0.0191 (13)
C9B	0.0357 (14)	0.0380 (15)	0.0368 (15)	0.0169 (12)	0.0076 (11)	0.0153 (12)
C10B	0.0386 (15)	0.0395 (15)	0.0355 (15)	0.0184 (13)	0.0110 (12)	0.0115 (12)
C11B	0.0442 (15)	0.0417 (16)	0.0370 (16)	0.0205 (13)	0.0121 (12)	0.0162 (13)
C12B	0.0549 (17)	0.0456 (17)	0.0521 (18)	0.0216 (15)	0.0182 (14)	0.0239 (15)
C13B	0.0582 (18)	0.0472 (19)	0.0496 (19)	0.0214 (16)	0.0211 (15)	0.0236 (15)
C14B	0.065 (2)	0.053 (2)	0.082 (2)	0.0184 (17)	0.0153 (18)	0.0326 (19)
C15B	0.091 (3)	0.051 (2)	0.094 (3)	0.015 (2)	0.013 (2)	0.033 (2)
C16B	0.107 (3)	0.059 (2)	0.089 (3)	0.031 (2)	0.034 (2)	0.045 (2)
C17B	0.116 (3)	0.081 (3)	0.070 (3)	0.032 (3)	0.004 (2)	0.047 (2)
C18B	0.097 (3)	0.057 (2)	0.052 (2)	0.014 (2)	0.0025 (19)	0.0265 (18)
C19B	0.0543 (17)	0.0489 (18)	0.0554 (19)	0.0228 (15)	0.0061 (14)	0.0227 (15)
C20B	0.0393 (15)	0.0560 (18)	0.0534 (19)	0.0207 (14)	0.0039 (13)	0.0227 (15)
C21B	0.0376 (15)	0.0462 (17)	0.0476 (18)	0.0148 (13)	0.0042 (13)	0.0192 (14)
C22B	0.0434 (15)	0.0467 (18)	0.060 (2)	0.0198 (14)	0.0065 (14)	0.0249 (16)
C23B	0.0405 (15)	0.0441 (16)	0.0494 (18)	0.0202 (13)	0.0120 (13)	0.0204 (14)
C24B	0.071 (2)	0.0383 (17)	0.054 (2)	0.0276 (16)	−0.0007 (16)	0.0130 (15)
C25B	0.063 (2)	0.055 (2)	0.090 (3)	0.0080 (18)	−0.0154 (19)	0.024 (2)
C26B	0.084 (3)	0.051 (3)	0.155 (5)	0.014 (2)	−0.047 (3)	0.013 (3)
C27B	0.154 (5)	0.066 (3)	0.122 (5)	0.063 (3)	−0.072 (4)	−0.031 (3)
C28B	0.174 (5)	0.088 (4)	0.066 (3)	0.086 (4)	−0.018 (3)	−0.008 (3)
C29B	0.124 (3)	0.064 (2)	0.057 (2)	0.058 (2)	0.009 (2)	0.009 (2)
C30B	0.0546 (18)	0.079 (2)	0.052 (2)	0.0277 (17)	0.0084 (15)	0.0362 (18)

Geometric parameters (Å, º)

O1A—C10A	1.228 (3)	O1B—C10B	1.223 (3)
O2A—C1A	1.214 (3)	O2B—C1B	1.225 (3)
N1A—C8A	1.460 (3)	N1B—C22B	1.468 (3)
N1A—C22A	1.463 (3)	N1B—C30B	1.472 (3)
N1A—C30A	1.473 (3)	N1B—C8B	1.472 (3)
N2A—C1A	1.359 (3)	N2B—C1B	1.343 (4)
N2A—C2A	1.397 (3)	N2B—C2B	1.397 (3)
N2A—H2AA	0.86	N2B—H2BA	0.86
C1A—C8A	1.571 (3)	C1B—C8B	1.571 (3)
C2A—C3A	1.377 (3)	C2B—C3B	1.374 (4)
C2A—C7A	1.398 (3)	C2B—C7B	1.400 (3)
C3A—C4A	1.381 (4)	C3B—C4B	1.377 (4)
C3A—H3AA	0.93	C3B—H3BA	0.93
C4A—C5A	1.377 (4)	C4B—C5B	1.375 (4)
C4A—H4AA	0.93	C4B—H4BA	0.93
C5A—C6A	1.386 (4)	C5B—C6B	1.395 (4)
C5A—H5AA	0.93	C5B—H5BA	0.93
C6A—C7A	1.385 (3)	C6B—C7B	1.374 (3)
C6A—H6AA	0.93	C6B—H6BA	0.93
C7A—C8A	1.523 (3)	C7B—C8B	1.518 (4)
C8A—C9A	1.596 (3)	C8B—C9B	1.588 (3)
C9A—C10A	1.535 (3)	C9B—C21B	1.533 (3)
C9A—C21A	1.543 (3)	C9B—C10B	1.552 (3)
C9A—C23A	1.579 (3)	C9B—C23B	1.572 (3)
C10A—C11A	1.489 (3)	C10B—C11B	1.488 (3)
C11A—C12A	1.332 (3)	C11B—C12B	1.342 (3)
C11A—C19A	1.513 (3)	C11B—C19B	1.515 (3)
C12A—C13A	1.467 (4)	C12B—C13B	1.466 (4)
C12A—H12A	0.93	C12B—H12B	0.93
C13A—C18A	1.384 (4)	C13B—C18B	1.376 (4)
C13A—C14A	1.386 (4)	C13B—C14B	1.393 (4)
C14A—C15A	1.383 (4)	C14B—C15B	1.369 (4)
C14A—H14A	0.93	C14B—H14B	0.93
C15A—C16A	1.367 (5)	C15B—C16B	1.371 (5)
C15A—H15A	0.93	C15B—H15B	0.93
C16A—C17A	1.356 (5)	C16B—C17B	1.366 (5)
C16A—H16A	0.93	C16B—H16B	0.93
C17A—C18A	1.369 (4)	C17B—C18B	1.390 (4)
C17A—H17A	0.93	C17B—H17B	0.93
C18A—H18A	0.93	C18B—H18B	0.93
C19A—C20A	1.521 (3)	C19B—C20B	1.518 (4)
C19A—H19A	0.97	C19B—H19C	0.97
C19A—H19B	0.97	C19B—H19D	0.97
C20A—C21A	1.521 (3)	C20B—C21B	1.512 (3)
C20A—H20A	0.97	C20B—H20C	0.97
C20A—H20B	0.97	C20B—H20D	0.97
C21A—H21A	0.97	C21B—H21C	0.97
C21A—H21B	0.97	C21B—H21D	0.97
C22A—C23A	1.538 (3)	C22B—C23B	1.525 (3)
C22A—H22A	0.97	C22B—H22C	0.97
C22A—H22B	0.97	C22B—H22D	0.97
C23A—C24A	1.515 (3)	C23B—C24B	1.513 (4)
C23A—H23A	0.98	C23B—H23B	0.98
C24A—C25A	1.369 (4)	C24B—C29B	1.375 (4)
C24A—C29A	1.380 (3)	C24B—C25B	1.399 (4)
C25A—C26A	1.385 (4)	C25B—C26B	1.389 (5)
C25A—H25A	0.93	C25B—H25B	0.93
C26A—C27A	1.359 (4)	C26B—C27B	1.356 (7)
C26A—H26A	0.93	C26B—H26B	0.93
C27A—C28A	1.339 (4)	C27B—C28B	1.362 (7)
C27A—H27A	0.93	C27B—H27B	0.93
C28A—C29A	1.393 (4)	C28B—C29B	1.381 (5)
C28A—H28A	0.93	C28B—H28B	0.93
C29A—H29A	0.93	C29B—H29B	0.93
C30A—H30A	0.96	C30B—H30D	0.96
C30A—H30B	0.96	C30B—H30E	0.96
C30A—H30C	0.96	C30B—H30F	0.96
C8A—N1A—C22A	106.6 (2)	C22B—N1B—C30B	113.0 (2)
C8A—N1A—C30A	115.8 (2)	C22B—N1B—C8B	106.5 (2)
C22A—N1A—C30A	113.8 (2)	C30B—N1B—C8B	114.4 (2)
C1A—N2A—C2A	112.2 (2)	C1B—N2B—C2B	112.7 (2)
C1A—N2A—H2AA	123.9	C1B—N2B—H2BA	123.6
C2A—N2A—H2AA	123.9	C2B—N2B—H2BA	123.6
O2A—C1A—N2A	124.8 (2)	O2B—C1B—N2B	125.9 (2)
O2A—C1A—C8A	127.2 (2)	O2B—C1B—C8B	126.0 (3)
N2A—C1A—C8A	108.0 (2)	N2B—C1B—C8B	108.0 (2)
C3A—C2A—N2A	128.0 (2)	C3B—C2B—N2B	128.1 (3)
C3A—C2A—C7A	122.4 (2)	C3B—C2B—C7B	122.5 (3)
N2A—C2A—C7A	109.6 (2)	N2B—C2B—C7B	109.3 (2)
C2A—C3A—C4A	117.8 (3)	C2B—C3B—C4B	118.0 (3)
C2A—C3A—H3AA	121.1	C2B—C3B—H3BA	121.0
C4A—C3A—H3AA	121.1	C4B—C3B—H3BA	121.0
C5A—C4A—C3A	120.9 (3)	C5B—C4B—C3B	120.9 (3)
C5A—C4A—H4AA	119.5	C5B—C4B—H4BA	119.6
C3A—C4A—H4AA	119.5	C3B—C4B—H4BA	119.6
C4A—C5A—C6A	120.9 (3)	C4B—C5B—C6B	120.6 (3)
C4A—C5A—H5AA	119.5	C4B—C5B—H5BA	119.7
C6A—C5A—H5AA	119.5	C6B—C5B—H5BA	119.7
C7A—C6A—C5A	119.3 (2)	C7B—C6B—C5B	119.6 (3)
C7A—C6A—H6AA	120.4	C7B—C6B—H6BA	120.2
C5A—C6A—H6AA	120.4	C5B—C6B—H6BA	120.2
C6A—C7A—C2A	118.6 (2)	C6B—C7B—C2B	118.4 (3)
C6A—C7A—C8A	131.9 (2)	C6B—C7B—C8B	132.3 (2)
C2A—C7A—C8A	109.4 (2)	C2B—C7B—C8B	109.1 (2)
N1A—C8A—C7A	112.32 (19)	N1B—C8B—C7B	110.90 (19)
N1A—C8A—C1A	113.03 (19)	N1B—C8B—C1B	111.46 (19)
C7A—C8A—C1A	100.61 (19)	C7B—C8B—C1B	100.8 (2)
N1A—C8A—C9A	101.25 (17)	N1B—C8B—C9B	102.11 (19)
C7A—C8A—C9A	118.94 (19)	C7B—C8B—C9B	120.28 (19)
C1A—C8A—C9A	111.22 (19)	C1B—C8B—C9B	111.53 (19)
C10A—C9A—C21A	109.54 (19)	C21B—C9B—C10B	109.3 (2)
C10A—C9A—C23A	107.86 (19)	C21B—C9B—C23B	114.4 (2)
C21A—C9A—C23A	113.5 (2)	C10B—C9B—C23B	108.7 (2)
C10A—C9A—C8A	107.22 (19)	C21B—C9B—C8B	114.03 (19)
C21A—C9A—C8A	114.83 (19)	C10B—C9B—C8B	106.42 (18)
C23A—C9A—C8A	103.37 (18)	C23B—C9B—C8B	103.58 (18)
O1A—C10A—C11A	119.0 (2)	O1B—C10B—C11B	120.3 (2)
O1A—C10A—C9A	119.2 (2)	O1B—C10B—C9B	119.0 (2)
C11A—C10A—C9A	121.8 (2)	C11B—C10B—C9B	120.6 (2)
C12A—C11A—C10A	116.3 (2)	C12B—C11B—C10B	116.9 (2)
C12A—C11A—C19A	124.6 (2)	C12B—C11B—C19B	123.0 (2)
C10A—C11A—C19A	119.1 (2)	C10B—C11B—C19B	120.1 (2)
C11A—C12A—C13A	127.9 (2)	C11B—C12B—C13B	129.7 (3)
C11A—C12A—H12A	116.1	C11B—C12B—H12B	115.1
C13A—C12A—H12A	116.1	C13B—C12B—H12B	115.1
C18A—C13A—C14A	117.4 (3)	C18B—C13B—C14B	117.6 (3)
C18A—C13A—C12A	122.4 (3)	C18B—C13B—C12B	123.9 (3)
C14A—C13A—C12A	119.9 (2)	C14B—C13B—C12B	118.5 (3)
C15A—C14A—C13A	119.9 (3)	C15B—C14B—C13B	121.2 (3)
C15A—C14A—H14A	120.0	C15B—C14B—H14B	119.4
C13A—C14A—H14A	120.0	C13B—C14B—H14B	119.4
C16A—C15A—C14A	121.2 (4)	C14B—C15B—C16B	120.5 (3)
C16A—C15A—H15A	119.4	C14B—C15B—H15B	119.7
C14A—C15A—H15A	119.4	C16B—C15B—H15B	119.7
C17A—C16A—C15A	119.2 (3)	C17B—C16B—C15B	119.4 (3)
C17A—C16A—H16A	120.4	C17B—C16B—H16B	120.3
C15A—C16A—H16A	120.4	C15B—C16B—H16B	120.3
C16A—C17A—C18A	120.3 (3)	C16B—C17B—C18B	120.3 (3)
C16A—C17A—H17A	119.8	C16B—C17B—H17B	119.8
C18A—C17A—H17A	119.8	C18B—C17B—H17B	119.8
C17A—C18A—C13A	121.8 (3)	C13B—C18B—C17B	120.9 (3)
C17A—C18A—H18A	119.1	C13B—C18B—H18B	119.5
C13A—C18A—H18A	119.1	C17B—C18B—H18B	119.5
C11A—C19A—C20A	111.5 (2)	C11B—C19B—C20B	113.4 (2)
C11A—C19A—H19A	109.3	C11B—C19B—H19C	108.9
C20A—C19A—H19A	109.3	C20B—C19B—H19C	108.9
C11A—C19A—H19B	109.3	C11B—C19B—H19D	108.9
C20A—C19A—H19B	109.3	C20B—C19B—H19D	108.9
H19A—C19A—H19B	108.0	H19C—C19B—H19D	107.7
C21A—C20A—C19A	110.0 (2)	C21B—C20B—C19B	110.2 (2)
C21A—C20A—H20A	109.7	C21B—C20B—H20C	109.6
C19A—C20A—H20A	109.7	C19B—C20B—H20C	109.6
C21A—C20A—H20B	109.7	C21B—C20B—H20D	109.6
C19A—C20A—H20B	109.7	C19B—C20B—H20D	109.6
H20A—C20A—H20B	108.2	H20C—C20B—H20D	108.1
C20A—C21A—C9A	113.9 (2)	C20B—C21B—C9B	113.3 (2)
C20A—C21A—H21A	108.8	C20B—C21B—H21C	108.9
C9A—C21A—H21A	108.8	C9B—C21B—H21C	108.9
C20A—C21A—H21B	108.8	C20B—C21B—H21D	108.9
C9A—C21A—H21B	108.8	C9B—C21B—H21D	108.9
H21A—C21A—H21B	107.7	H21C—C21B—H21D	107.7
N1A—C22A—C23A	104.15 (19)	N1B—C22B—C23B	103.7 (2)
N1A—C22A—H22A	110.9	N1B—C22B—H22C	111.0
C23A—C22A—H22A	110.9	C23B—C22B—H22C	111.0
N1A—C22A—H22B	110.9	N1B—C22B—H22D	111.0
C23A—C22A—H22B	110.9	C23B—C22B—H22D	111.0
H22A—C22A—H22B	108.9	H22C—C22B—H22D	109.0
C24A—C23A—C22A	114.4 (2)	C24B—C23B—C22B	114.4 (2)
C24A—C23A—C9A	118.9 (2)	C24B—C23B—C9B	117.2 (2)
C22A—C23A—C9A	104.74 (19)	C22B—C23B—C9B	105.6 (2)
C24A—C23A—H23A	105.9	C24B—C23B—H23B	106.3
C22A—C23A—H23A	105.9	C22B—C23B—H23B	106.3
C9A—C23A—H23A	105.9	C9B—C23B—H23B	106.3
C25A—C24A—C29A	116.8 (3)	C29B—C24B—C25B	117.3 (3)
C25A—C24A—C23A	124.2 (2)	C29B—C24B—C23B	120.1 (3)
C29A—C24A—C23A	119.0 (2)	C25B—C24B—C23B	122.6 (3)
C24A—C25A—C26A	121.5 (3)	C26B—C25B—C24B	120.0 (4)
C24A—C25A—H25A	119.2	C26B—C25B—H25B	120.0
C26A—C25A—H25A	119.2	C24B—C25B—H25B	120.0
C27A—C26A—C25A	120.5 (3)	C27B—C26B—C25B	121.3 (5)
C27A—C26A—H26A	119.7	C27B—C26B—H26B	119.3
C25A—C26A—H26A	119.7	C25B—C26B—H26B	119.3
C28A—C27A—C26A	119.2 (3)	C26B—C27B—C28B	119.1 (5)
C28A—C27A—H27A	120.4	C26B—C27B—H27B	120.4
C26A—C27A—H27A	120.4	C28B—C27B—H27B	120.4
C27A—C28A—C29A	120.8 (3)	C27B—C28B—C29B	120.5 (5)
C27A—C28A—H28A	119.6	C27B—C28B—H28B	119.7
C29A—C28A—H28A	119.6	C29B—C28B—H28B	119.7
C24A—C29A—C28A	121.1 (3)	C24B—C29B—C28B	121.6 (4)
C24A—C29A—H29A	119.5	C24B—C29B—H29B	119.2
C28A—C29A—H29A	119.5	C28B—C29B—H29B	119.2
N1A—C30A—H30A	109.5	N1B—C30B—H30D	109.5
N1A—C30A—H30B	109.5	N1B—C30B—H30E	109.5
H30A—C30A—H30B	109.5	H30D—C30B—H30E	109.5
N1A—C30A—H30C	109.5	N1B—C30B—H30F	109.5
H30A—C30A—H30C	109.5	H30D—C30B—H30F	109.5
H30B—C30A—H30C	109.5	H30E—C30B—H30F	109.5
C2A—N2A—C1A—O2A	−174.4 (2)	C2B—N2B—C1B—O2B	175.6 (3)
C2A—N2A—C1A—C8A	4.7 (3)	C2B—N2B—C1B—C8B	−1.3 (3)
C1A—N2A—C2A—C3A	175.0 (2)	C1B—N2B—C2B—C3B	−175.4 (3)
C1A—N2A—C2A—C7A	−3.3 (3)	C1B—N2B—C2B—C7B	1.2 (3)
N2A—C2A—C3A—C4A	−176.7 (2)	N2B—C2B—C3B—C4B	175.7 (3)
C7A—C2A—C3A—C4A	1.4 (4)	C7B—C2B—C3B—C4B	−0.4 (4)
C2A—C3A—C4A—C5A	−0.4 (4)	C2B—C3B—C4B—C5B	−0.3 (4)
C3A—C4A—C5A—C6A	0.7 (4)	C3B—C4B—C5B—C6B	0.3 (4)
C4A—C5A—C6A—C7A	−2.0 (4)	C4B—C5B—C6B—C7B	0.4 (4)
C5A—C6A—C7A—C2A	2.9 (4)	C5B—C6B—C7B—C2B	−1.1 (4)
C5A—C6A—C7A—C8A	177.0 (2)	C5B—C6B—C7B—C8B	−174.9 (3)
C3A—C2A—C7A—C6A	−2.7 (4)	C3B—C2B—C7B—C6B	1.1 (4)
N2A—C2A—C7A—C6A	175.7 (2)	N2B—C2B—C7B—C6B	−175.7 (2)
C3A—C2A—C7A—C8A	−178.0 (2)	C3B—C2B—C7B—C8B	176.3 (2)
N2A—C2A—C7A—C8A	0.4 (3)	N2B—C2B—C7B—C8B	−0.5 (3)
C22A—N1A—C8A—C7A	172.73 (19)	C22B—N1B—C8B—C7B	−171.4 (2)
C30A—N1A—C8A—C7A	−59.6 (3)	C30B—N1B—C8B—C7B	63.1 (3)
C22A—N1A—C8A—C1A	−74.3 (2)	C22B—N1B—C8B—C1B	77.1 (3)
C30A—N1A—C8A—C1A	53.4 (3)	C30B—N1B—C8B—C1B	−48.4 (3)
C22A—N1A—C8A—C9A	44.8 (2)	C22B—N1B—C8B—C9B	−42.1 (2)
C30A—N1A—C8A—C9A	172.5 (2)	C30B—N1B—C8B—C9B	−167.60 (19)
C6A—C7A—C8A—N1A	−51.8 (3)	C6B—C7B—C8B—N1B	55.9 (3)
C2A—C7A—C8A—N1A	122.6 (2)	C2B—C7B—C8B—N1B	−118.4 (2)
C6A—C7A—C8A—C1A	−172.3 (2)	C6B—C7B—C8B—C1B	174.0 (3)
C2A—C7A—C8A—C1A	2.2 (2)	C2B—C7B—C8B—C1B	−0.3 (2)
C6A—C7A—C8A—C9A	66.1 (3)	C6B—C7B—C8B—C9B	−63.0 (4)
C2A—C7A—C8A—C9A	−119.5 (2)	C2B—C7B—C8B—C9B	122.7 (2)
O2A—C1A—C8A—N1A	55.1 (3)	O2B—C1B—C8B—N1B	−58.2 (3)
N2A—C1A—C8A—N1A	−124.0 (2)	N2B—C1B—C8B—N1B	118.7 (2)
O2A—C1A—C8A—C7A	175.0 (2)	O2B—C1B—C8B—C7B	−175.9 (3)
N2A—C1A—C8A—C7A	−4.1 (2)	N2B—C1B—C8B—C7B	0.9 (3)
O2A—C1A—C8A—C9A	−58.0 (3)	O2B—C1B—C8B—C9B	55.2 (3)
N2A—C1A—C8A—C9A	122.8 (2)	N2B—C1B—C8B—C9B	−127.9 (2)
N1A—C8A—C9A—C10A	84.8 (2)	N1B—C8B—C9B—C21B	149.49 (19)
C7A—C8A—C9A—C10A	−38.7 (3)	C7B—C8B—C9B—C21B	−87.3 (3)
C1A—C8A—C9A—C10A	−154.8 (2)	C1B—C8B—C9B—C21B	30.4 (3)
N1A—C8A—C9A—C21A	−153.2 (2)	N1B—C8B—C9B—C10B	−89.9 (2)
C7A—C8A—C9A—C21A	83.2 (3)	C7B—C8B—C9B—C10B	33.3 (3)
C1A—C8A—C9A—C21A	−32.9 (3)	C1B—C8B—C9B—C10B	150.9 (2)
N1A—C8A—C9A—C23A	−29.0 (2)	N1B—C8B—C9B—C23B	24.5 (2)
C7A—C8A—C9A—C23A	−152.5 (2)	C7B—C8B—C9B—C23B	147.7 (2)
C1A—C8A—C9A—C23A	91.3 (2)	C1B—C8B—C9B—C23B	−94.6 (2)
C21A—C9A—C10A—O1A	157.1 (2)	C21B—C9B—C10B—O1B	−156.2 (2)
C23A—C9A—C10A—O1A	33.1 (3)	C23B—C9B—C10B—O1B	−30.8 (3)
C8A—C9A—C10A—O1A	−77.6 (3)	C8B—C9B—C10B—O1B	80.2 (3)
C21A—C9A—C10A—C11A	−24.6 (3)	C21B—C9B—C10B—C11B	25.7 (3)
C23A—C9A—C10A—C11A	−148.7 (2)	C23B—C9B—C10B—C11B	151.2 (2)
C8A—C9A—C10A—C11A	100.6 (2)	C8B—C9B—C10B—C11B	−97.9 (2)
O1A—C10A—C11A—C12A	19.8 (3)	O1B—C10B—C11B—C12B	−13.8 (4)
C9A—C10A—C11A—C12A	−158.5 (2)	C9B—C10B—C11B—C12B	164.3 (2)
O1A—C10A—C11A—C19A	−162.5 (2)	O1B—C10B—C11B—C19B	168.4 (2)
C9A—C10A—C11A—C19A	19.3 (3)	C9B—C10B—C11B—C19B	−13.6 (3)
C10A—C11A—C12A—C13A	−176.8 (2)	C10B—C11B—C12B—C13B	−179.5 (2)
C19A—C11A—C12A—C13A	5.5 (4)	C19B—C11B—C12B—C13B	−1.7 (4)
C11A—C12A—C13A—C18A	51.0 (4)	C11B—C12B—C13B—C18B	−39.5 (4)
C11A—C12A—C13A—C14A	−134.9 (3)	C11B—C12B—C13B—C14B	142.6 (3)
C18A—C13A—C14A—C15A	−2.9 (4)	C18B—C13B—C14B—C15B	1.6 (5)
C12A—C13A—C14A—C15A	−177.4 (3)	C12B—C13B—C14B—C15B	179.7 (3)
C13A—C14A—C15A—C16A	2.6 (5)	C13B—C14B—C15B—C16B	−0.6 (5)
C14A—C15A—C16A—C17A	−0.8 (5)	C14B—C15B—C16B—C17B	−0.3 (6)
C15A—C16A—C17A—C18A	−0.6 (5)	C15B—C16B—C17B—C18B	0.2 (6)
C16A—C17A—C18A—C13A	0.1 (5)	C14B—C13B—C18B—C17B	−1.8 (5)
C14A—C13A—C18A—C17A	1.7 (4)	C12B—C13B—C18B—C17B	−179.7 (3)
C12A—C13A—C18A—C17A	175.9 (3)	C16B—C17B—C18B—C13B	0.9 (5)
C12A—C11A—C19A—C20A	144.4 (3)	C12B—C11B—C19B—C20B	−153.1 (3)
C10A—C11A—C19A—C20A	−33.2 (3)	C10B—C11B—C19B—C20B	24.6 (3)
C11A—C19A—C20A—C21A	54.3 (3)	C11B—C19B—C20B—C21B	−48.9 (3)
C19A—C20A—C21A—C9A	−64.3 (3)	C19B—C20B—C21B—C9B	65.5 (3)
C10A—C9A—C21A—C20A	46.9 (3)	C10B—C9B—C21B—C20B	−51.6 (3)
C23A—C9A—C21A—C20A	167.5 (2)	C23B—C9B—C21B—C20B	−173.7 (2)
C8A—C9A—C21A—C20A	−73.8 (3)	C8B—C9B—C21B—C20B	67.3 (3)
C8A—N1A—C22A—C23A	−42.7 (2)	C30B—N1B—C22B—C23B	169.15 (19)
C30A—N1A—C22A—C23A	−171.6 (2)	C8B—N1B—C22B—C23B	42.8 (2)
N1A—C22A—C23A—C24A	153.2 (2)	N1B—C22B—C23B—C24B	−155.2 (2)
N1A—C22A—C23A—C9A	21.3 (2)	N1B—C22B—C23B—C9B	−24.8 (3)
C10A—C9A—C23A—C24A	122.1 (2)	C21B—C9B—C23B—C24B	4.0 (3)
C21A—C9A—C23A—C24A	0.5 (3)	C10B—C9B—C23B—C24B	−118.4 (3)
C8A—C9A—C23A—C24A	−124.6 (2)	C8B—C9B—C23B—C24B	128.7 (2)
C10A—C9A—C23A—C22A	−108.6 (2)	C21B—C9B—C23B—C22B	−124.7 (2)
C21A—C9A—C23A—C22A	129.8 (2)	C10B—C9B—C23B—C22B	112.9 (2)
C8A—C9A—C23A—C22A	4.8 (2)	C8B—C9B—C23B—C22B	0.0 (2)
C22A—C23A—C24A—C25A	−48.2 (4)	C22B—C23B—C24B—C29B	−132.8 (3)
C9A—C23A—C24A—C25A	76.5 (3)	C9B—C23B—C24B—C29B	102.8 (3)
C22A—C23A—C24A—C29A	129.4 (3)	C22B—C23B—C24B—C25B	45.6 (4)
C9A—C23A—C24A—C29A	−105.9 (3)	C9B—C23B—C24B—C25B	−78.8 (3)
C29A—C24A—C25A—C26A	0.9 (5)	C29B—C24B—C25B—C26B	0.1 (5)
C23A—C24A—C25A—C26A	178.6 (3)	C23B—C24B—C25B—C26B	−178.3 (3)
C24A—C25A—C26A—C27A	−1.6 (6)	C24B—C25B—C26B—C27B	0.3 (6)
C25A—C26A—C27A—C28A	1.5 (6)	C25B—C26B—C27B—C28B	−1.9 (7)
C26A—C27A—C28A—C29A	−0.8 (5)	C26B—C27B—C28B—C29B	3.3 (7)
C25A—C24A—C29A—C28A	−0.1 (4)	C25B—C24B—C29B—C28B	1.3 (5)
C23A—C24A—C29A—C28A	−177.9 (3)	C23B—C24B—C29B—C28B	179.7 (3)
C27A—C28A—C29A—C24A	0.1 (5)	C27B—C28B—C29B—C24B	−3.0 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12A—H12A···O1A	0.93	2.33	2.704 (3)	103
C12B—H12B···O1B	0.93	2.34	2.730 (3)	105
C23A—H23A···O1A	0.98	2.23	2.751 (3)	112
C23B—H23B···O1B	0.98	2.23	2.764 (3)	113
N2A—H2AA···N1B^i	0.86	2.33	3.029 (3)	139
N2B—H2BA···O1A^ii	0.86	2.06	2.848 (3)	153

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