2,5-Dimethyl-6,7-dihydro­benzo[h]­pyrazolo[1,5-a]quinazoline and 2-tert-butyl-5-methyl-6,7-dihydro­benzo[h]pyrazolo[1,5-a]quinazoline

In both 2,5-dimethyl-6,7-dihydro­benzo[h]pyrazolo[1,5-a]­quinazoline, C₁₆H₁₅N₃, (I), and 2-tert-butyl-5-methyl-6,7-dihydro­benzo[h]pyrazolo[1,5-a]quinazoline, C₁₉H₂₁N₃, (II), which crystallizes with Z' = 2 in the space group P, the non-aromatic carbocyclic rings adopt screw-boat conformations. The mol­ecules of (I) are linked into chains of rings by a combination of C-H...N and C-H...[pi](arene) hydrogen bonds, while in (II) there are no hydrogen bonds of any kind.

S1. Comment

We report here the structures of two closely related 6,7-dihydrobenzo[h]pyrazolo[1,5-a]quinazolines, (I) and (II) (Figs. 1 and 2), both prepared using solvent-free cyclocondensation reactions between 2-acetyltetralone and the appropriate 3-alkyl-5-amino-1H-pyrazole. We compare the molecular and supramolecular structures of compounds (I) and (II) with those of the related aryl compounds (III) and (IV) (Portilla et al., 2005) and with that of compound (V) (Low et al., 2004).

In (I) and in each of the independent molecules of (II), the non-aromatic carbocyclic rings adopt a screw-boat conformation. The ring-puckering amplitudes (Cremer & Pople 1975) are 0.506 (2) Å in (I), and 0.481 (2) and 0.482 (3) Å, respectively, for the molecules of types 1 and 2 (containing atoms N11 and N21, see Fig. 2) in (II). In (I), the corresponding ring-puckering angles are θ = 69.0 (2)° and ϕ = 82.6 (3)° for the atom sequence C5A—C6—C7—C7A—C11A—C11B; in (II), for the atom sequences Cx1A—Cx1B—Cx5A—Cx6—Cx7—Cx7A (where x = 1 for molecule 1 and 2 for molecule 2), θ = 67.5 (2)° and ϕ = 210.6 (3)° when x = 1, and θ = 67.0 (2)° and ϕ = 213.4 (3)° when x = 2. For an idealized screw-boat conformation, the values are θ = 67.5° and ϕ = (60n + 30)°, where n represents zero or an integer (Evans & Boeyens, 1989). Similar conformation have been found for the corresponding rings in compounds (III)–(V) (Low et al., 2004; Portilla et al., 2005). Because of the puckering of the non-aromatic carbocyclic rings, the molecules exhibit no internal symmetry and hence they are chiral; however, the centrosymmetric space group in each case accommodates equal numbers of the two enantiomeric forms.

Within the heterobicyclic portions of the molecules, the patterns of the bond distances (Tables 1 and 3) are very similar for all three molecules. Hence we discuss in detail only the distances in (I), as similar remarks apply to (II). In (I), N1—C2 and C3A—N4 the bonds, which are formally double and single bonds respectively, are effectively of the same length; on the other hand, the C5—C5A bond, which is formally a single bond, is significantly longer than the C2—C3 and C5A—C11B bonds, which are formally double bonds. These observations are consistent with bond-fixation of the type characteristic of naphthalene rather than complete peripheral delocalization of the ten π electrons. By contrast, the distances in the carbocylic ring (C7A/C8–C11/C11A) are indicative of typical aromatic delocalization.

The geometries and conformations of the two independent molecules in (II) are very similar. Although the ADDSYM routine in PLATON (Spek, 2003) indicated that no additional crystallographic symmetry is present in (II), examination of the atom coordinates showed that the two independent molecules are approximately related by a pseudo-c-glide plane at x = 0.25. Consistent with this approximate relationship, the reflections of type (0kl) are, in general, very much weaker when l is odd than when l is even, although some exhibit significant intensity.

Two hydrogen bonds (Table 2) link the molecules of (I) into chains of rings. Atom C3 in the molecule at (x, y, z) acts as a hydrogen-bond donor to the ring atom N4 in the molecule at (1 - x, -y, 2 - z), so generating by inversion a cyclic centrosymmetric R²₂(8) (Bernstein et al., 1995) dimer centred at (1/2, 0, 1). At the same time, atom C7 in the molecule at (x, y, z), acts as a hydrogen-bond donor, via the axial atom H7B, to the C7A/C8–C11/C11A ring in the molecule at (1 - x, 1 - y, 1 - z), thus generating by inversion a second cyclic motif centred at (1/2, 1/2, 1/2). The propagation by inversion of these two hydrogen bonds therefore leads to the formation of a chain of centrosymmetric hydrogen-bonded rings running parallel to the [011] direction, with the rings formed by pairs of C—H···N hydrogen bonds centred at (1/2, n, 1 - n) (where n represents zero or an integer) alternating with the rings formed by pairs of C—H···π(arene) hydrogen bonds centred at (1/2, 1/2 + n, 1/2 - n) (where n represents zero or an integer) (Fig. 3). There is a very weak π–π stacking interaction between pairs of pyrimidine rings. These rings in the molecules at (x, y, z) and (1 - x, 1 - y, 2 - z) are strictly parallel with an interplanar spacing of 3.354 (2) Å; the ring-centroid separation is 3.840 (2) Å, corresponding to a ring-centroid offset of 1.870 (2) Å. If this interaction is regarded as significant, its action is to link the hydrogen-bonded chains into a sheet parallel to (100).

The supramolecular aggregation in (II), by contrast, is extremely simple. There are no hydrogen bonds of any kind in the structure, but the molecules of type 1 are linked in pairs by a single weak π–π stacking interaction between the phenyl rings of the molecules at (x, y, z) and (-x, -y, -z). The interplanar spacing is 3.395 (2) Å, with a ring-centroid separation of 3.974 (2) Å, which corresponds to a ring-centroid offset of 1.867 (2) Å. There are no direction-specific interactions of any kind involving the molecules of type 2.

The stacking interaction in (II) closely resembles that in the 4-methylphenyl analogue (IV) (Portilla et al.,2005), where pairs of molecules are again linked into isolated dimers. In the unsubstituted phenyl compound (III), the molecules are linked into chains by a combination of a C—H···π(arene) hydrogen bond and a π–π stacking interaction. The 4-chlorophenyl derivative (V) crystallizes with Z' = 2 (Low et al., 2004), and the molecules are linked by two independent π–π stacking interactions into chains in which the two types of molecules alternate.

Related literature

For related literature, see: Bernstein et al. (1995); Cremer & Pople (1975); Evans & Boeyens (1989); Low et al. (2004); Portilla et al. (2005); Spek (2003).

S2. Experimental

Equimolar quantities (2.6 mmol of each component) of 2-acetyltetralone and either 5-amino-3-methyl-1H-pyrazole for (I), or 5-amino-3-tert-butyl-1H-pyrazole for (II), were thoroughly mixed at room temperature. The solvent-free mixtures were then heated in an oil bath at 393 K for 1.5–2 min. The resulting melts were stirred briefly, and then allowed to cool to ambient temperature to solidify. The resulting solids were extracted with ethanol and, after removal of the solvent under reduced pressure, the products (I) and (II) were recrystallized from dimethylformamide to give crystals suitable for single-crystal X-ray diffraction. (I), pale orange [colourless according to CIF] crystals, yield 86%, m.p. 385–387 K; MS (70 eV) m/z (%): 249 (100, M⁺), 234 (8), 221 (9), 127 (16), 39 (22). (II), pale yellow [colourless according to CIF] crystals, yield 84% m.p. 439–441 K; MS (70 eV) m/z (%): 291 (96, M⁺), 276 (92), 246 (100), 128 (25), 57 (25), 41 (57), 39 (56).

S3. Refinement

Crystals of both (I) and (II) are triclinic, and for each the space group P1 was selected, and confirmed by the structure analysis. All H atoms were located in difference maps, and then treated as riding atoms in geometrically idealized position with C—H distances 0.95 Å (aromatic), 0.98 Å (CH₃) or 0.99 Å (CH₂), and with U_iso(H) = kU_eq(C), where k = 1.5 for the methyl groups and 1.2 for all other H atoms. A search for possible additional symmetry in (II) revealed none.

Computing details

For both compounds, data collection: COLLECT (Hooft, 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: OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures

	Fig. 1. A molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The two independent molecules of compound (II) showing the atom-labelling scheme: (a) a molecule of type 1 containing atom N11 and (b) a molecule of type 2 containing atom N21. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 3. A stereoview of part of the crystal structure of (I), showing the formation of a hydrogen-bonded chain of rings along [011]. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.

(I) 2,5-Dimethyl-6,7-dihydrobenzo[h]pyrazolo[1,5-a]quinazoline

Crystal data

C16H15N3	Z = 2
Mr = 249.31	F(000) = 264
Triclinic, P1	Dx = 1.328 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9430 (19) Å	Cell parameters from 2867 reflections
b = 7.9660 (11) Å	θ = 3.1–27.5°
c = 9.943 (3) Å	µ = 0.08 mm^−1
α = 87.637 (13)°	T = 120 K
β = 82.632 (18)°	Plate, pale orange
γ = 89.941 (17)°	0.49 × 0.44 × 0.07 mm
V = 623.4 (3) Å^3

Data collection

Bruker–Nonius KappaCCD diffractometer	2867 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1600 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
ϕ and ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→10
Tmin = 0.971, Tmax = 0.994	k = −10→10
15496 measured reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.220	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.132P)^2] where P = (Fo^2 + 2Fc^2)/3
2867 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

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

	x	y	z	Uiso*/Ueq
N1	0.2113 (2)	0.2787 (2)	0.7554 (2)	0.0334 (5)
C2	0.1988 (3)	0.1266 (3)	0.8210 (2)	0.0346 (6)
C21	0.0519 (3)	0.0156 (3)	0.8068 (3)	0.0441 (7)
C3	0.3322 (3)	0.0946 (3)	0.8954 (3)	0.0371 (6)
C3A	0.4344 (3)	0.2341 (3)	0.8756 (2)	0.0318 (6)
N4	0.5821 (2)	0.2726 (2)	0.92127 (19)	0.0334 (5)
C5	0.6519 (3)	0.4197 (3)	0.8817 (2)	0.0316 (6)
C51	0.8150 (3)	0.4574 (3)	0.9349 (2)	0.0374 (6)
C5A	0.5806 (3)	0.5352 (3)	0.7918 (2)	0.0295 (6)
C6	0.6642 (3)	0.6992 (3)	0.7433 (2)	0.0343 (6)
C7	0.6505 (3)	0.7289 (3)	0.5925 (2)	0.0323 (6)
C7A	0.4709 (3)	0.7192 (3)	0.5656 (2)	0.0301 (6)
C8	0.4136 (3)	0.8146 (3)	0.4611 (2)	0.0333 (6)
C9	0.2461 (3)	0.8055 (3)	0.4363 (3)	0.0373 (6)
C10	0.1328 (3)	0.7036 (3)	0.5176 (2)	0.0369 (6)
C11	0.1873 (3)	0.6047 (3)	0.6217 (2)	0.0347 (6)
C11A	0.3564 (3)	0.6090 (3)	0.6450 (2)	0.0290 (6)
C11B	0.4299 (3)	0.4968 (3)	0.7447 (2)	0.0285 (6)
N11C	0.3571 (2)	0.3450 (2)	0.78920 (19)	0.0295 (5)
H21A	0.0501	−0.0066	0.7108	0.066*
H21B	−0.0538	0.0711	0.8422	0.066*
H21C	0.0626	−0.0907	0.8581	0.066*
H3	0.3492	−0.0038	0.9491	0.044*
H51A	0.9104	0.4399	0.8641	0.056*
H51B	0.8266	0.3826	1.0139	0.056*
H51C	0.8149	0.5745	0.9617	0.056*
H6A	0.7851	0.6967	0.7580	0.041*
H6B	0.6081	0.7918	0.7952	0.041*
H7A	0.6977	0.8410	0.5619	0.039*
H7B	0.7184	0.6436	0.5402	0.039*
H8	0.4903	0.8876	0.4056	0.040*
H9	0.2097	0.8699	0.3629	0.045*
H10	0.0171	0.7008	0.5027	0.044*
H11	0.1088	0.5337	0.6775	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0313 (12)	0.0351 (12)	0.0344 (11)	−0.0050 (9)	−0.0074 (9)	0.0003 (9)
C2	0.0367 (15)	0.0342 (14)	0.0327 (13)	0.0012 (11)	−0.0048 (11)	0.0016 (11)
C21	0.0426 (16)	0.0424 (16)	0.0477 (16)	−0.0064 (12)	−0.0096 (13)	0.0057 (12)
C3	0.0372 (15)	0.0367 (14)	0.0370 (14)	0.0010 (11)	−0.0056 (12)	0.0041 (11)
C3A	0.0313 (14)	0.0379 (14)	0.0259 (12)	0.0046 (11)	−0.0040 (10)	0.0016 (10)
N4	0.0330 (12)	0.0399 (12)	0.0278 (11)	0.0029 (9)	−0.0057 (9)	0.0007 (9)
C5	0.0306 (13)	0.0380 (14)	0.0267 (12)	0.0024 (10)	−0.0054 (10)	−0.0013 (10)
C51	0.0306 (14)	0.0501 (16)	0.0325 (14)	0.0015 (11)	−0.0075 (11)	−0.0027 (12)
C5A	0.0283 (13)	0.0340 (13)	0.0261 (12)	0.0016 (10)	−0.0028 (10)	−0.0037 (10)
C6	0.0350 (14)	0.0332 (13)	0.0352 (14)	0.0001 (11)	−0.0057 (11)	−0.0034 (11)
C7	0.0313 (14)	0.0307 (13)	0.0347 (14)	−0.0004 (10)	−0.0043 (11)	0.0003 (11)
C7A	0.0328 (14)	0.0280 (13)	0.0296 (12)	0.0039 (10)	−0.0043 (10)	−0.0030 (10)
C8	0.0347 (14)	0.0308 (13)	0.0343 (13)	0.0009 (10)	−0.0054 (11)	−0.0002 (11)
C9	0.0428 (16)	0.0342 (14)	0.0368 (14)	0.0022 (11)	−0.0122 (12)	−0.0012 (11)
C10	0.0294 (14)	0.0378 (14)	0.0449 (15)	0.0046 (11)	−0.0090 (12)	−0.0025 (12)
C11	0.0281 (14)	0.0351 (14)	0.0405 (14)	0.0002 (10)	−0.0039 (11)	0.0008 (11)
C11A	0.0304 (13)	0.0296 (13)	0.0277 (12)	0.0026 (10)	−0.0049 (10)	−0.0040 (10)
C11B	0.0281 (13)	0.0303 (13)	0.0268 (12)	0.0002 (10)	−0.0023 (10)	−0.0021 (10)
N11C	0.0265 (11)	0.0341 (11)	0.0281 (11)	0.0007 (8)	−0.0052 (8)	0.0010 (9)

Geometric parameters (Å, º)

N1—C2	1.350 (3)	C5A—C6	1.499 (3)
C2—C3	1.385 (4)	C6—C7	1.526 (3)
C3—C3A	1.370 (3)	C6—H6A	0.99
C3A—N4	1.351 (3)	C6—H6B	0.99
N4—C5	1.320 (3)	C7—C7A	1.488 (3)
C5—C5A	1.423 (3)	C7—H7A	0.99
C5A—C11B	1.379 (3)	C7—H7B	0.99
C11B—N11C	1.372 (3)	C7A—C8	1.385 (3)
N11C—N1	1.360 (3)	C7A—C11A	1.408 (3)
C3A—N11C	1.402 (3)	C8—C9	1.386 (3)
C2—C21	1.489 (3)	C8—H8	0.95
C21—H21A	0.98	C9—C10	1.372 (3)
C21—H21B	0.98	C9—H9	0.95
C21—H21C	0.98	C10—C11	1.388 (3)
C3—H3	0.95	C10—H10	0.95
C5—C51	1.497 (3)	C11—C11A	1.393 (3)
C51—H51A	0.98	C11—H11	0.95
C51—H51B	0.98	C11A—C11B	1.482 (3)
C51—H51C	0.98
C2—N1—N11C	104.10 (18)	C7—C6—H6B	109.8
N1—C2—C3	112.6 (2)	H6A—C6—H6B	108.3
N1—C2—C21	119.3 (2)	C7A—C7—C6	111.13 (19)
C3—C2—C21	128.1 (2)	C7A—C7—H7A	109.4
C2—C21—H21A	109.5	C6—C7—H7A	109.4
C2—C21—H21B	109.5	C7A—C7—H7B	109.4
H21A—C21—H21B	109.5	C6—C7—H7B	109.4
C2—C21—H21C	109.5	H7A—C7—H7B	108.0
H21A—C21—H21C	109.5	C8—C7A—C11A	118.7 (2)
H21B—C21—H21C	109.5	C8—C7A—C7	121.3 (2)
C3A—C3—C2	105.9 (2)	C11A—C7A—C7	120.1 (2)
C3A—C3—H3	127.1	C7A—C8—C9	121.1 (2)
C2—C3—H3	127.1	C7A—C8—H8	119.4
N4—C3A—C3	132.1 (2)	C9—C8—H8	119.4
N4—C3A—N11C	121.8 (2)	C10—C9—C8	120.1 (2)
C3—C3A—N11C	106.1 (2)	C10—C9—H9	119.9
C5—N4—C3A	117.4 (2)	C8—C9—H9	119.9
N4—C5—C5A	123.0 (2)	C9—C10—C11	120.0 (2)
N4—C5—C51	115.7 (2)	C9—C10—H10	120.0
C5A—C5—C51	121.3 (2)	C11—C10—H10	120.0
C5—C51—H51A	109.5	C10—C11—C11A	120.4 (2)
C5—C51—H51B	109.5	C10—C11—H11	119.8
H51A—C51—H51B	109.5	C11A—C11—H11	119.8
C5—C51—H51C	109.5	C11—C11A—C7A	119.6 (2)
H51A—C51—H51C	109.5	C11—C11A—C11B	124.3 (2)
H51B—C51—H51C	109.5	C7A—C11A—C11B	116.0 (2)
C11B—C5A—C5	119.9 (2)	N11C—C11B—C5A	116.4 (2)
C11B—C5A—C6	117.5 (2)	N11C—C11B—C11A	121.9 (2)
C5—C5A—C6	122.6 (2)	C5A—C11B—C11A	121.6 (2)
C5A—C6—C7	109.26 (19)	N1—N11C—C11B	127.18 (19)
C5A—C6—H6A	109.8	N1—N11C—C3A	111.30 (19)
C7—C6—H6A	109.8	C11B—N11C—C3A	121.5 (2)
C5A—C6—H6B	109.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N4^i	0.95	2.55	3.495 (3)	175
C7—H7B···Cg^ii	0.99	2.97	3.789 (3)	141

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

(II) 2-tert-Butyl-5-methyl-6,7-dihydrobenzo[h]pyrazolo[1,5-a]quinazoline

Crystal data

C19H21N3	Z = 4
Mr = 291.39	F(000) = 624
Triclinic, P1	Dx = 1.270 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.2632 (5) Å	Cell parameters from 6991 reflections
b = 11.4574 (7) Å	θ = 3.3–27.5°
c = 12.1317 (6) Å	µ = 0.08 mm^−1
α = 93.449 (5)°	T = 120 K
β = 90.313 (4)°	Plate, pale yellow
γ = 102.791 (6)°	0.52 × 0.35 × 0.15 mm
V = 1523.66 (14) Å^3

Data collection

Bruker–Nonius KappaCCD diffractometer	6991 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	4144 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
ϕ and ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −14→14
Tmin = 0.972, Tmax = 0.989	k = −14→14
37817 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.213	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.112P)^2 + 0.7885P] where P = (Fo^2 + 2Fc^2)/3
6991 reflections	(Δ/σ)max < 0.001
405 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

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

	x	y	z	Uiso*/Ueq
N11	−0.08028 (18)	0.23561 (18)	0.22469 (16)	0.0251 (5)
C12	−0.1426 (2)	0.2742 (2)	0.3086 (2)	0.0256 (5)
C121	−0.2776 (2)	0.2234 (2)	0.3140 (2)	0.0262 (5)
C122	−0.2987 (2)	0.1016 (2)	0.3654 (3)	0.0394 (7)
C123	−0.3360 (2)	0.3096 (3)	0.3846 (2)	0.0361 (6)
C124	−0.3344 (2)	0.2068 (3)	0.1978 (2)	0.0367 (7)
C13	−0.0666 (2)	0.3564 (2)	0.3832 (2)	0.0263 (5)
C13A	0.0496 (2)	0.3677 (2)	0.34248 (19)	0.0244 (5)
N14	0.15925 (18)	0.42942 (18)	0.38278 (16)	0.0262 (5)
C15	0.2563 (2)	0.4153 (2)	0.3269 (2)	0.0247 (5)
C151	0.3777 (2)	0.4774 (2)	0.3765 (2)	0.0309 (6)
C15A	0.2485 (2)	0.3441 (2)	0.22562 (19)	0.0235 (5)
C16	0.3596 (2)	0.3320 (2)	0.1612 (2)	0.0281 (6)
C17	0.3425 (2)	0.2065 (2)	0.1057 (2)	0.0270 (5)
C17A	0.2270 (2)	0.1742 (2)	0.0378 (2)	0.0247 (5)
C18	0.2199 (2)	0.1075 (2)	−0.0621 (2)	0.0277 (6)
C19	0.1128 (2)	0.0790 (2)	−0.1247 (2)	0.0290 (6)
C110	0.0127 (2)	0.1194 (2)	−0.0881 (2)	0.0281 (6)
C111	0.0166 (2)	0.1848 (2)	0.0122 (2)	0.0258 (5)
C11A	0.1235 (2)	0.2122 (2)	0.07662 (19)	0.0226 (5)
C11B	0.1367 (2)	0.2840 (2)	0.18268 (19)	0.0221 (5)
N11C	0.03751 (17)	0.29473 (17)	0.24558 (16)	0.0225 (4)
N21	0.54131 (18)	0.76318 (18)	0.27332 (16)	0.0251 (5)
C22	0.4613 (2)	0.7232 (2)	0.1894 (2)	0.0243 (5)
C221	0.3478 (2)	0.7725 (2)	0.1843 (2)	0.0271 (5)
C222	0.3788 (3)	0.8926 (2)	0.1309 (3)	0.0388 (7)
C223	0.2499 (2)	0.6853 (2)	0.1147 (2)	0.0345 (6)
C224	0.2998 (2)	0.7903 (3)	0.3005 (2)	0.0391 (7)
C23	0.5003 (2)	0.6421 (2)	0.1150 (2)	0.0245 (5)
C23A	0.6119 (2)	0.6321 (2)	0.15577 (19)	0.0222 (5)
N24	0.69424 (18)	0.57077 (18)	0.11621 (16)	0.0255 (5)
C25	0.7983 (2)	0.5853 (2)	0.17177 (19)	0.0240 (5)
C252	0.8909 (2)	0.5232 (2)	0.1234 (2)	0.0297 (6)
C25A	0.8231 (2)	0.6578 (2)	0.27291 (19)	0.0238 (5)
C26	0.9404 (2)	0.6700 (2)	0.3370 (2)	0.0284 (6)
C27	0.9783 (2)	0.7949 (2)	0.3942 (2)	0.0259 (5)
C27A	0.8775 (2)	0.8241 (2)	0.4631 (2)	0.0239 (5)
C28	0.8997 (2)	0.8861 (2)	0.5658 (2)	0.0258 (5)
C29	0.8056 (2)	0.9120 (2)	0.6284 (2)	0.0285 (6)
C210	0.6872 (2)	0.8770 (2)	0.5880 (2)	0.0271 (5)
C211	0.6624 (2)	0.8151 (2)	0.4860 (2)	0.0250 (5)
C21A	0.7567 (2)	0.7878 (2)	0.42219 (19)	0.0231 (5)
C21B	0.7382 (2)	0.7173 (2)	0.31500 (19)	0.0218 (5)
N21C	0.63371 (17)	0.70587 (17)	0.25265 (16)	0.0225 (4)
H12A	−0.2625	0.0464	0.3187	0.059*
H12B	−0.3864	0.0688	0.3708	0.059*
H12C	−0.2607	0.1119	0.4391	0.059*
H12D	−0.3018	0.3184	0.4598	0.054*
H12E	−0.4242	0.2775	0.3865	0.054*
H12F	−0.3198	0.3879	0.3526	0.054*
H12G	−0.3242	0.2849	0.1660	0.055*
H12H	−0.4214	0.1697	0.2016	0.055*
H12I	−0.2942	0.1547	0.1512	0.055*
H13	−0.0900	0.3958	0.4480	0.032*
H51A	0.3658	0.5246	0.4440	0.046*
H51B	0.4231	0.5308	0.3235	0.046*
H51C	0.4238	0.4176	0.3944	0.046*
H16A	0.4317	0.3481	0.2116	0.034*
H16B	0.3745	0.3918	0.1044	0.034*
H17A	0.4126	0.2027	0.0577	0.032*
H17B	0.3401	0.1478	0.1628	0.032*
H18	0.2894	0.0807	−0.0881	0.033*
H19	0.1086	0.0318	−0.1923	0.035*
H110	−0.0599	0.1019	−0.1320	0.034*
H111	−0.0535	0.2111	0.0371	0.031*
H22A	0.4122	0.8814	0.0574	0.058*
H22B	0.4392	0.9500	0.1768	0.058*
H22C	0.3049	0.9237	0.1234	0.058*
H22D	0.2322	0.6071	0.1472	0.052*
H22E	0.2789	0.6760	0.0393	0.052*
H22F	0.1756	0.7164	0.1128	0.052*
H22G	0.3636	0.8433	0.3466	0.059*
H22H	0.2760	0.7124	0.3331	0.059*
H22I	0.2288	0.8263	0.2962	0.059*
H23	0.4588	0.6023	0.0501	0.029*
H52A	0.8573	0.4760	0.0558	0.045*
H52B	0.9123	0.4700	0.1767	0.045*
H52C	0.9639	0.5830	0.1057	0.045*
H26A	1.0051	0.6559	0.2863	0.034*
H26B	0.9298	0.6091	0.3928	0.034*
H27A	1.0511	0.7992	0.4418	0.031*
H27B	1.0004	0.8548	0.3380	0.031*
H28	0.9811	0.9111	0.5934	0.031*
H29	0.8221	0.9534	0.6991	0.034*
H210	0.6224	0.8955	0.6306	0.033*
H211	0.5807	0.7910	0.4592	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0255 (11)	0.0243 (10)	0.0247 (11)	0.0042 (8)	0.0011 (8)	0.0006 (8)
C12	0.0298 (13)	0.0226 (12)	0.0255 (13)	0.0075 (10)	0.0019 (10)	0.0042 (10)
C121	0.0243 (12)	0.0286 (13)	0.0255 (13)	0.0054 (10)	0.0022 (10)	0.0021 (10)
C122	0.0330 (15)	0.0356 (15)	0.0490 (18)	0.0043 (12)	0.0038 (13)	0.0101 (13)
C123	0.0309 (14)	0.0390 (16)	0.0376 (15)	0.0070 (12)	0.0065 (12)	−0.0024 (12)
C124	0.0283 (14)	0.0483 (17)	0.0310 (15)	0.0038 (12)	−0.0027 (11)	−0.0003 (13)
C13	0.0330 (14)	0.0259 (13)	0.0217 (12)	0.0105 (10)	0.0023 (10)	0.0008 (10)
C13A	0.0312 (13)	0.0217 (12)	0.0203 (12)	0.0058 (10)	0.0005 (10)	0.0009 (10)
N14	0.0292 (11)	0.0228 (10)	0.0255 (11)	0.0041 (9)	−0.0009 (9)	0.0005 (8)
C15	0.0298 (13)	0.0212 (12)	0.0234 (12)	0.0053 (10)	−0.0004 (10)	0.0048 (10)
C151	0.0291 (13)	0.0301 (14)	0.0310 (14)	0.0027 (11)	−0.0010 (11)	−0.0038 (11)
C15A	0.0280 (13)	0.0213 (12)	0.0210 (12)	0.0048 (10)	0.0010 (10)	0.0025 (9)
C16	0.0255 (13)	0.0290 (13)	0.0290 (13)	0.0045 (10)	0.0035 (10)	0.0011 (11)
C17	0.0264 (13)	0.0303 (13)	0.0256 (13)	0.0084 (10)	0.0034 (10)	0.0039 (10)
C17A	0.0278 (13)	0.0216 (12)	0.0250 (13)	0.0055 (10)	0.0038 (10)	0.0034 (10)
C18	0.0324 (14)	0.0250 (13)	0.0269 (13)	0.0085 (10)	0.0052 (11)	0.0037 (10)
C19	0.0382 (14)	0.0258 (13)	0.0217 (12)	0.0047 (11)	0.0021 (11)	0.0001 (10)
C110	0.0318 (14)	0.0276 (13)	0.0240 (13)	0.0041 (11)	−0.0008 (10)	0.0020 (10)
C111	0.0283 (13)	0.0256 (13)	0.0233 (12)	0.0053 (10)	0.0021 (10)	0.0022 (10)
C11A	0.0278 (13)	0.0190 (11)	0.0210 (12)	0.0043 (9)	0.0013 (10)	0.0038 (9)
C11B	0.0246 (12)	0.0215 (12)	0.0210 (12)	0.0059 (9)	0.0019 (9)	0.0045 (9)
N11C	0.0229 (10)	0.0238 (10)	0.0201 (10)	0.0034 (8)	−0.0002 (8)	0.0010 (8)
N21	0.0253 (11)	0.0239 (10)	0.0267 (11)	0.0070 (8)	0.0001 (8)	0.0001 (9)
C22	0.0245 (12)	0.0228 (12)	0.0242 (12)	0.0016 (9)	−0.0013 (10)	0.0037 (10)
C221	0.0272 (13)	0.0279 (13)	0.0267 (13)	0.0074 (10)	−0.0024 (10)	0.0014 (10)
C222	0.0369 (15)	0.0302 (14)	0.0507 (18)	0.0083 (12)	−0.0003 (13)	0.0102 (13)
C223	0.0305 (14)	0.0341 (14)	0.0381 (15)	0.0073 (11)	−0.0068 (11)	−0.0034 (12)
C224	0.0345 (15)	0.0534 (18)	0.0326 (15)	0.0175 (13)	0.0018 (12)	−0.0021 (13)
C23	0.02457 (12)	0.0259 (12)	0.0217 (12)	0.0021 (10)	−0.0012 (10)	0.0025 (10)
C23A	0.0246 (12)	0.0209 (12)	0.0203 (12)	0.0036 (9)	0.0013 (9)	0.0007 (9)
N24	0.0271 (11)	0.0243 (11)	0.0252 (11)	0.0063 (8)	0.0008 (8)	0.0009 (8)
C25	0.0264 (12)	0.0220 (12)	0.0221 (12)	0.0022 (10)	0.0010 (10)	0.0026 (10)
C252	0.0299 (14)	0.0285 (13)	0.0308 (14)	0.0080 (11)	−0.0008 (11)	−0.0026 (11)
C25A	0.0252 (12)	0.0220 (12)	0.0238 (12)	0.0040 (10)	0.0012 (10)	0.0028 (10)
C26	0.0284 (13)	0.0302 (13)	0.0271 (13)	0.0073 (10)	0.0008 (10)	0.0009 (11)
C27	0.0258 (12)	0.0278 (13)	0.0226 (12)	0.0030 (10)	−0.0016 (10)	0.0016 (10)
C27A	0.0275 (13)	0.0196 (12)	0.0240 (12)	0.0032 (10)	0.0004 (10)	0.0035 (10)
C28	0.0268 (13)	0.0240 (12)	0.0242 (12)	0.0002 (10)	−0.0032 (10)	0.0031 (10)
C29	0.0368 (14)	0.0247 (13)	0.0223 (12)	0.0035 (11)	−0.0002 (10)	−0.0007 (10)
C210	0.0305 (13)	0.0281 (13)	0.0229 (12)	0.0067 (10)	0.0025 (10)	0.0018 (10)
C211	0.0256 (12)	0.0246 (12)	0.0233 (12)	0.0020 (10)	0.0008 (10)	0.0033 (10)
C21A	0.0296 (13)	0.0192 (11)	0.0194 (12)	0.0024 (9)	−0.0018 (10)	0.0040 (9)
C21B	0.0216 (12)	0.0212 (12)	0.0213 (12)	0.0014 (9)	0.0000 (9)	0.0041 (9)
N21C	0.0223 (10)	0.0238 (10)	0.0212 (10)	0.0052 (8)	−0.0007 (8)	−0.0001 (8)

Geometric parameters (Å, º)

N11—C12	1.347 (3)	N21—C22	1.345 (3)
C12—C13	1.404 (3)	C22—C23	1.399 (3)
C13—C13A	1.383 (3)	C23—C23A	1.379 (3)
C13A—N14	1.353 (3)	C23A—N24	1.355 (3)
N14—C15	1.324 (3)	N24—C25	1.323 (3)
C15—C15A	1.424 (3)	C25—C25A	1.430 (3)
C15A—C11B	1.377 (3)	C25A—C21B	1.375 (3)
C11B—N11C	1.381 (3)	C21B—N21C	1.373 (3)
N11C—N11	1.364 (3)	N21C—N21	1.365 (3)
C13A—N11C	1.389 (3)	C23A—N21C	1.393 (3)
C12—C121	1.506 (3)	C22—C221	1.511 (3)
C121—C123	1.527 (4)	C221—C223	1.527 (4)
C121—C124	1.530 (3)	C221—C222	1.530 (4)
C121—C122	1.533 (4)	C221—C224	1.531 (4)
C122—H12A	0.98	C222—H22A	0.98
C122—H12B	0.98	C222—H22B	0.98
C122—H12C	0.98	C222—H22C	0.98
C123—H12D	0.98	C223—H22D	0.98
C123—H12E	0.98	C223—H22E	0.98
C123—H12F	0.98	C223—H22F	0.98
C124—H12G	0.98	C224—H22G	0.98
C124—H12H	0.98	C224—H22H	0.98
C124—H12I	0.98	C224—H22I	0.98
C13—H13	0.95	C23—H23	0.95
C15—C151	1.500 (3)	C25—C252	1.491 (3)
C151—H51A	0.98	C252—H52A	0.98
C151—H51B	0.98	C252—H52B	0.98
C151—H51C	0.98	C252—H52C	0.98
C15A—C16	1.508 (3)	C25A—C26	1.504 (3)
C16—C17	1.523 (3)	C26—C27	1.522 (3)
C16—H16A	0.99	C26—H26A	0.99
C16—H16B	0.99	C26—H26B	0.99
C17—C17A	1.499 (3)	C27—C27A	1.498 (3)
C17—H17A	0.99	C27—H27A	0.99
C17—H17B	0.99	C27—H27B	0.99
C17A—C18	1.387 (3)	C27A—C28	1.389 (3)
C17A—C11A	1.405 (3)	C27A—C21A	1.410 (3)
C18—C19	1.386 (3)	C28—C29	1.384 (3)
C18—H18	0.95	C28—H28	0.95
C19—C110	1.377 (4)	C29—C210	1.383 (3)
C19—H19	0.95	C29—H29	0.95
C110—C111	1.385 (3)	C210—C211	1.384 (3)
C110—H110	0.95	C210—H210	0.95
C111—C11A	1.398 (3)	C211—C21A	1.397 (3)
C111—H111	0.95	C211—H211	0.95
C11A—C11B	1.474 (3)	C21A—C21B	1.478 (3)
C12—N11—N11C	104.26 (19)	C22—N21—N21C	104.16 (18)
N11—C12—C13	112.3 (2)	N21—C22—C23	112.7 (2)
N11—C12—C121	118.8 (2)	N21—C22—C221	118.3 (2)
C13—C12—C121	128.9 (2)	C23—C22—C221	128.9 (2)
C12—C121—C123	109.4 (2)	C22—C221—C223	109.5 (2)
C12—C121—C124	110.0 (2)	C22—C221—C222	108.7 (2)
C123—C121—C124	109.3 (2)	C223—C221—C222	109.3 (2)
C12—C121—C122	108.9 (2)	C22—C221—C224	110.5 (2)
C123—C121—C122	110.0 (2)	C223—C221—C224	109.1 (2)
C124—C121—C122	109.3 (2)	C222—C221—C224	109.8 (2)
C121—C122—H12A	109.5	C221—C222—H22A	109.5
C121—C122—H12B	109.5	C221—C222—H22B	109.5
H12A—C122—H12B	109.5	H22A—C222—H22B	109.5
C121—C122—H12C	109.5	C221—C222—H22C	109.5
H12A—C122—H12C	109.5	H22A—C222—H22C	109.5
H12B—C122—H12C	109.5	H22B—C222—H22C	109.5
C121—C123—H12D	109.5	C221—C223—H22D	109.5
C121—C123—H12E	109.5	C221—C223—H22E	109.5
H12D—C123—H12E	109.5	H22D—C223—H22E	109.5
C121—C123—H12F	109.5	C221—C223—H22F	109.5
H12D—C123—H12F	109.5	H22D—C223—H22F	109.5
H12E—C123—H12F	109.5	H22E—C223—H22F	109.5
C121—C124—H12G	109.5	C221—C224—H22G	109.5
C121—C124—H12H	109.5	C221—C224—H22H	109.5
H12G—C124—H12H	109.5	H22G—C224—H22H	109.5
C121—C124—H12I	109.5	C221—C224—H22I	109.5
H12G—C124—H12I	109.5	H22G—C224—H22I	109.5
H12H—C124—H12I	109.5	H22H—C224—H22I	109.5
C13A—C13—C12	105.3 (2)	C23A—C23—C22	105.2 (2)
C13A—C13—H13	127.3	C23A—C23—H23	127.4
C12—C13—H13	127.3	C22—C23—H23	127.4
N14—C13A—C13	131.6 (2)	N24—C23A—C23	131.7 (2)
N14—C13A—N11C	122.2 (2)	N24—C23A—N21C	121.9 (2)
C13—C13A—N11C	106.1 (2)	C23—C23A—N21C	106.3 (2)
C15—N14—C13A	117.0 (2)	C25—N24—C23A	117.5 (2)
N14—C15—C15A	122.9 (2)	N24—C25—C25A	122.4 (2)
N14—C15—C151	116.4 (2)	N24—C25—C252	116.8 (2)
C15A—C15—C151	120.6 (2)	C25A—C25—C252	120.8 (2)
C15—C151—H51A	109.5	C25—C252—H52A	109.5
C15—C151—H51B	109.5	C25—C252—H52B	109.5
H51A—C151—H51B	109.5	H52A—C252—H52B	109.5
C15—C151—H51C	109.5	C25—C252—H52C	109.5
H51A—C151—H51C	109.5	H52A—C252—H52C	109.5
H51B—C151—H51C	109.5	H52B—C252—H52C	109.5
C11B—C15A—C15	120.2 (2)	C21B—C25A—C25	120.2 (2)
C11B—C15A—C16	117.5 (2)	C21B—C25A—C26	118.2 (2)
C15—C15A—C16	122.3 (2)	C25—C25A—C26	121.7 (2)
C15A—C16—C17	110.6 (2)	C25A—C26—C27	110.3 (2)
C15A—C16—H16A	109.5	C25A—C26—H26A	109.6
C17—C16—H16A	109.5	C27—C26—H26A	109.6
C15A—C16—H16B	109.5	C25A—C26—H26B	109.6
C17—C16—H16B	109.5	C27—C26—H26B	109.6
H16A—C16—H16B	108.1	H26A—C26—H26B	108.1
C17A—C17—C16	110.9 (2)	C27A—C27—C26	111.0 (2)
C17A—C17—H17A	109.4	C27A—C27—H27A	109.4
C16—C17—H17A	109.4	C26—C27—H27A	109.4
C17A—C17—H17B	109.4	C27A—C27—H27B	109.4
C16—C17—H17B	109.4	C26—C27—H27B	109.4
H17A—C17—H17B	108.0	H27A—C27—H27B	108.0
C18—C17A—C11A	119.3 (2)	C28—C27A—C21A	119.2 (2)
C18—C17A—C17	121.5 (2)	C28—C27A—C27	121.9 (2)
C11A—C17A—C17	119.2 (2)	C21A—C27A—C27	118.9 (2)
C19—C18—C17A	121.0 (2)	C29—C28—C27A	121.2 (2)
C19—C18—H18	119.5	C29—C28—H28	119.4
C17A—C18—H18	119.5	C27A—C28—H28	119.4
C110—C19—C18	119.6 (2)	C210—C29—C28	119.6 (2)
C110—C19—H19	120.2	C210—C29—H29	120.2
C18—C19—H19	120.2	C28—C29—H29	120.2
C19—C110—C111	120.7 (2)	C29—C210—C211	120.4 (2)
C19—C110—H110	119.6	C29—C210—H210	119.8
C111—C110—H110	119.6	C211—C210—H210	119.8
C110—C111—C11A	120.0 (2)	C210—C211—C21A	120.5 (2)
C110—C111—H111	120.0	C210—C211—H211	119.7
C11A—C111—H111	120.0	C21A—C211—H211	119.7
C111—C11A—C17A	119.4 (2)	C211—C21A—C27A	119.1 (2)
C111—C11A—C11B	123.6 (2)	C211—C21A—C21B	124.2 (2)
C17A—C11A—C11B	116.9 (2)	C27A—C21A—C21B	116.7 (2)
C15A—C11B—N11C	115.7 (2)	N21C—C21B—C25A	116.3 (2)
C15A—C11B—C11A	122.3 (2)	N21C—C21B—C21A	121.5 (2)
N11C—C11B—C11A	121.9 (2)	C25A—C21B—C21A	122.2 (2)
N11—N11C—C11B	126.17 (19)	N21—N21C—C21B	126.72 (19)
N11—N11C—C13A	111.99 (18)	N21—N21C—C23A	111.59 (18)
C11B—N11C—C13A	121.81 (19)	C21B—N21C—C23A	121.68 (19)
N11C—N11—C12—C13	−0.4 (3)	N21C—N21—C22—C23	−0.3 (3)
N11C—N11—C12—C121	−178.1 (2)	N21C—N21—C22—C221	−178.0 (2)
N11—C12—C121—C123	−158.5 (2)	N21—C22—C221—C223	−158.1 (2)
C13—C12—C121—C123	24.3 (3)	C23—C22—C221—C223	24.7 (3)
N11—C12—C121—C124	−38.5 (3)	N21—C22—C221—C222	82.6 (3)
C13—C12—C121—C124	144.3 (3)	C23—C22—C221—C222	−94.6 (3)
N11—C12—C121—C122	81.3 (3)	N21—C22—C221—C224	−37.9 (3)
C13—C12—C121—C122	−95.9 (3)	C23—C22—C221—C224	144.9 (3)
N11—C12—C13—C13A	−0.5 (3)	N21—C22—C23—C23A	−0.2 (3)
C121—C12—C13—C13A	176.9 (2)	C221—C22—C23—C23A	177.0 (2)
C12—C13—C13A—N14	−176.2 (2)	C22—C23—C23A—N24	−176.8 (2)
C12—C13—C13A—N11C	1.2 (3)	C22—C23—C23A—N21C	0.7 (2)
C13—C13A—N14—C15	175.4 (2)	C23—C23A—N24—C25	175.8 (2)
N11C—C13A—N14—C15	−1.6 (3)	N21C—C23A—N24—C25	−1.5 (3)
C13A—N14—C15—C15A	3.3 (3)	C23A—N24—C25—C25A	3.1 (3)
C13A—N14—C15—C151	−175.9 (2)	C23A—N24—C25—C252	−176.3 (2)
N14—C15—C15A—C11B	−1.5 (4)	N24—C25—C25A—C21B	−1.2 (4)
C151—C15—C15A—C11B	177.7 (2)	C252—C25—C25A—C21B	178.1 (2)
N14—C15—C15A—C16	178.1 (2)	N24—C25—C25A—C26	177.9 (2)
C151—C15—C15A—C16	−2.8 (3)	C252—C25—C25A—C26	−2.7 (3)
C11B—C15A—C16—C17	−35.5 (3)	C21B—C25A—C26—C27	−34.2 (3)
C15—C15A—C16—C17	145.0 (2)	C25—C25A—C26—C27	146.6 (2)
C15A—C16—C17—C17A	53.3 (3)	C25A—C26—C27—C27A	53.6 (3)
C16—C17—C17A—C18	143.0 (2)	C26—C27—C27A—C28	140.8 (2)
C16—C17—C17A—C11A	−37.2 (3)	C26—C27—C27A—C21A	−39.3 (3)
C11A—C17A—C18—C19	0.8 (4)	C21A—C27A—C28—C29	0.4 (4)
C17—C17A—C18—C19	−179.4 (2)	C27—C27A—C28—C29	−179.7 (2)
C17A—C18—C19—C110	1.2 (4)	C27A—C28—C29—C210	−0.8 (4)
C18—C19—C110—C111	−2.0 (4)	C28—C29—C210—C211	0.8 (4)
C19—C110—C111—C11A	1.0 (4)	C29—C210—C211—C21A	−0.4 (4)
C110—C111—C11A—C17A	1.0 (4)	C210—C211—C21A—C27A	0.0 (3)
C110—C111—C11A—C11B	178.3 (2)	C210—C211—C21A—C21B	176.9 (2)
C18—C17A—C11A—C111	−1.8 (3)	C28—C27A—C21A—C211	0.0 (3)
C17—C17A—C11A—C111	178.4 (2)	C27—C27A—C21A—C211	−179.9 (2)
C18—C17A—C11A—C11B	−179.4 (2)	C28—C27A—C21A—C21B	−177.2 (2)
C17—C17A—C11A—C11B	0.8 (3)	C27—C27A—C21A—C21B	3.0 (3)
C15—C15A—C11B—N11C	−2.1 (3)	C25—C25A—C21B—N21C	−2.3 (3)
C16—C15A—C11B—N11C	178.3 (2)	C26—C25A—C21B—N21C	178.5 (2)
C15—C15A—C11B—C11A	178.1 (2)	C25—C25A—C21B—C21A	176.6 (2)
C16—C15A—C11B—C11A	−1.4 (3)	C26—C25A—C21B—C21A	−2.5 (3)
C111—C11A—C11B—C15A	−157.1 (2)	C211—C21A—C21B—N21C	21.6 (3)
C17A—C11A—C11B—C15A	20.3 (3)	C27A—C21A—C21B—N21C	−161.4 (2)
C111—C11A—C11B—N11C	23.1 (3)	C211—C21A—C21B—C25A	−157.3 (2)
C17A—C11A—C11B—N11C	−159.4 (2)	C27A—C21A—C21B—C25A	19.7 (3)
C12—N11—N11C—C11B	179.3 (2)	C22—N21—N21C—C21B	179.7 (2)
C12—N11—N11C—C13A	1.2 (2)	C22—N21—N21C—C23A	0.8 (2)
C15A—C11B—N11C—N11	−174.1 (2)	C25A—C21B—N21C—N21	−174.9 (2)
C11A—C11B—N11C—N11	5.7 (3)	C21A—C21B—N21C—N21	6.1 (3)
C15A—C11B—N11C—C13A	3.8 (3)	C25A—C21B—N21C—C23A	3.9 (3)
C11A—C11B—N11C—C13A	−176.4 (2)	C21A—C21B—N21C—C23A	−175.0 (2)
N14—C13A—N11C—N11	176.1 (2)	N24—C23A—N21C—N21	176.9 (2)
C13—C13A—N11C—N11	−1.6 (3)	C23—C23A—N21C—N21	−1.0 (3)
N14—C13A—N11C—C11B	−2.1 (3)	N24—C23A—N21C—C21B	−2.1 (3)
C13—C13A—N11C—C11B	−179.7 (2)	C23—C23A—N21C—C21B	−180.0 (2)