A π-stacked chain of hydrogen-bonded dimers in 3-tert-butyl-1-(4-chloro­phen­yl)-4-phenyl­indeno­[1,2-b]pyrazolo­[4,3-e]pyridin-5(1H)-one and a π-stacked sheet of hydrogen-bonded chains in 3-tert-butyl-1-(4-chloro­phen­yl)-4-(4-meth­oxy­phen­yl)indeno­[1,2-b]pyrazolo­[4,3-e]pyridin-5(1H)-one

In 3-tert-butyl-1-(4-chloro­phen­yl)-4-phenyl­indeno­[1,2-b]pyra­zolo­[4,3-e]pyridin-5(1H)-one, C₂₉H₂₂ClN₃O, (I), inversion-related pairs of mol­ecules are linked by C—H...O hydrogen bonds to form R₂²(18) dimers, which are themselves linked into a chain by a π–π stacking inter­action between inversion-related pairs of mol­ecules. In 3-tert-butyl-1-(4-chloro­phen­yl)-4-(4-meth­oxy­phen­yl)indeno­[1,2-b]pyrazolo­[4,3-e]pyridin-5(1H)-one, C₃₀H₂₄ClN₃O₂, (II), which crystallizes in the space group P, with Z′ = 2 and with different orientations for the meth­oxy groups in the two independent mol­ecules, a combination of C—H...O and C—H...π(arene) hydrogen bonds links the mol­ecules into chains of rings, which are further linked into sheets by a π–π stacking inter­action.

S1. Comment

Pyrazolo[3,4-b]pyridines are fused heterocyclic compounds of considerable interest for drug development because of the wide range of biological activities that they exhibit (Quiroga et al., 2005, 2007). Independently, indenopyridine compounds have shown potential activity as antioxidant, antihistamine and antidepressant agents (de Almeida et al., 1976; Strunz & Findlay, 1985; Earl et al., 1998; Padwa et al., 2000; Peters et al., 2004; Evdokimov et al., 2011). As part of a programme whose aim is to prepare new heterocyclic derivatives combining both these fused ring systems, we report here the structure of 3-tert-butyl-1-(4-chlorophenyl)-4–phenylindeno[1,2-b]pyrazolo[4,3-e]pyridin-5(1H)-one, (I), and the 4-(4-methoxyphenyl)- derivative, (II) (Figs. 1 and 2), which were prepared in good yield by means of a tricomponent reaction between indan-1,3-dione, the corresponding substituted benzaldehyde and 5-amino-3-tert-butyl-1-(4-chlorophenyl)-1H-pyrazole (see Scheme), which was induced by smooth microwave irradiation using water as solvent and triethylamine as catalyst.

Compounds (I) and (II) both crystallize in the space group P1, but with Z' values of 1 and 2, respectively (Figs. 1 and 2); in (II) it will be convenient to refer to the molecules having x = 1 and 2 as type 1 and type 2 molecules, respectively. For each of the independent molecules, the conformations can be defined in terms of the orientations of the tert-butyl group and of the two pendent aryl substituents relative to the fused ring system, along with the orientation of the methoxy groups in (II).

None of the molecules exhibits any internal symmetry and hence they are all conformationally chiral; however, in each compound the centrosymmetric space group accommodates equal numbers of both conformational enantiomers. In each of the independent molecules, the fused ring system is essentially planar. In compound (I), the maximum deviations from the mean plane through the fused ring system are 0.060 (2) Å for atom C3 and 0.045 (2) Å for atom C5A, displaced to opposite sides of the plane; for the type 1 molecule in compound (II), the maximum deviations are 0.118 (2) Å for atom C17 and 0.086 (2) Å for atom C19B, again displaced to opposite sides of the plane; and in the type 2 molecule of compound (II), the maximum deviations are 0.086 (2) Å for atom C23 and 0.057 (2) Å for atom C28, this time with both displaced to the same side of the mean plane. Amongst the three independent molecules, no obvious pattern for these displacements can be recognized, so that the displacements are not regarded as chemically or structurally significant.

The corresponding bond distances within the fused ring systems are very similar, and they are consistent with aromatic delocalization in the fused aryl ring, and with delocalization in the pyridine ring accompanied by strong bond fixation in the pyrazole ring, as typically observed in pyrazolopyridine derivatives (Low et al., 2007; Quiroga et al., 2009, 2010; Insuasty et al., 2010).

The key torsion angles (Table 1) confirm that the two independent molecules within the selected asymmetric unit of compound (II) have the same conformation, which is the same as that for the selected asymmetric unit in compound (I). The corresponding values for each of the torsion angles amongst the three independent molecular species are remarkably similar. In each case, one of the methyl C atoms of the tert-butyl group, designated C32 in compound (I) and C132 and C232 in the two independent molecules of compound (II) (Figs. 1 and 2), lies close to, but not exactly in, the plane of the adjacent pyrazole ring. The deviations of this atom from the pyrazole plane are 0.388 (2) Å for atom C32 in compound (I), and 0.210 (2) Å and 0.386 (2) Å for atoms C132 and C232, respectively, in compound (II). Curiously, however, the two independent molecules in compound (II) exhibit different orientations for their methoxy groups (Table 1 and Fig. 2), and this alone suffices to preclude the possibility of any additional crystallographic symmetry.

Despite their close similarity in both constitution and conformation, the molecules of compounds (I) and (II) show different patterns of supramolecular aggregation, leading to arrays which are one- and two-dimensional, respectively.

In the crystal structure of (I), inversion-related pairs of molecules are linked by rather long and weak C—H···O hydrogen bonds (Table 2) into centrosymmetric R₂²(18) (Bernstein et al., 1995) dimers, and these hydrogen-bonded dimers are linked into chains by a single π–π stacking interaction. The planes of the pyridine ring in the molecule at (x, y, z) and the fused aryl ring in the molecule at (-x+1, -y+1, -z+1) make a dihedral angle of only 1.2 (2)°; the corresponding ring-centroid separation is 3.573 (2) Å and the interplanar spacing is ca 3.36 Å, giving a ring-centroid offset of ca 1.22 Å. The effect of this π-stacking interaction is to link the hydrogen-bonded dimers into a chain running parallel to the [001] direction, with the hydrogen-bonded rings centred at (1/2, 1/2, n), where n represents an integer, alternating with the π-stacking interactions across (1/2, 1/2, n + 1/2), where n again represents an integer (Fig. 3). It is notable that neither of the pendent aryl rings, viz. C11–C16 and C41–C46, participates in any π–π stacking interactions and that, despite the number of aromatic rings present, there are no C—H···π hydrogen bonds in the structure of (I).

The direction-specific intermolecular interactions in the crystal structure of compound (II) differ from those in the structure of compound (I) in several respects: firstly, Z' = 2 in compound (II); secondly, there is a C—H···π(arene) hydrogen bond present; and thirdly, this hydrogen bond involves both types of pendent aryl ring, with the 4-methoxyphenyl ring in the type 1 molecule providing the donor and the 4-chlorophenyl ring in the type 2 molecule acting as the acceptor.

The single, fairly short C—H···π(arene) hydrogen bond (Table 2) links the two independent molecules in the selected asymmetric unit. Two independent C—H···O hydrogen bonds, each linking inversion-related pairs of molecules into R₂²(14) rings, thus generate, in combination with the C—H···π(arene) hydrogen bond, a chain of rings running parallel to the [110] direction (Fig. 4). There are two independent π–π stacking interactions present in the structure of compound (II). The first of these occurs within the selected asymmetric unit, where the fused aryl ring of the type 1 molecule and the pyridine ring of the the type 2 molecule make a dihedral angle of 2.5 (2)°; the ring-centroid separation is 3.701 (2) Å and the interplanar separation is ca 3.53 Å, corresponding to a ring-centroid offset of ca 1.11 Å. Hence this interaction provides some modest reinforcement to the action of the C—H···π(arene) hydrogen bond.

Only type 2 molecules of compound (II) are involved in the second type of stacking interaction. The pyridine ring of the type 2 molecule at (x, y, z) and the fused aryl ring of the type 2 molecule at (1 - x, 1 - y, 1 - z) make a dihedral angle of 2.2 (2)°, with a ring-centroid separation off 3.743 (2) Å, an interplanar spacing of ca 3.56 Å, and a ring-centroid offset of ca 1.16 Å (Fig. 5). The effect of this interaction is to link the hydrogen-bonded chains into a sheet parallel to (001). It may be noted here that the overall behaviour of this π-stacking interaction of the type 2 molecules of compound (II) closely corresponds to the π-stacking interaction in compound (I), although the metrics of the two interaction differ somewhat, not surprisingly in view of the presence of an additional molecular type in compound (II).

Related literature

For related literature, see: de Almeida et al. (1976); Bernstein et al. (1995); Earl et al. (1998); Evdokimov et al. (2011); Insuasty et al. (2010); Low et al. (2007); Padwa et al. (2000); Peters et al. (2004); Quiroga et al. (2005, 2007, 2009, 2010); Strunz & Findlay (1985).

S2. Experimental

For the synthesis of compounds (I) and (II), equimolar quantities (1 mmol of each component) of indan-1,3-dione 4-R-benzaldehyde, where R = H for compound (I) and R = OMe for compound (II) and 5-amino-3-tert-butyl-1-(4-chlorophenyl)-1H-pyrazole were added to a mixture of water/triethylamine (3 ml, 15:1 v/v), and then subjected to microwave irradiation at 353 K with a maximum power of 80 W for 10 min. The reaction mixture was allowed to cool to ambient temperature and it was then extracted with dichloromethane (3 × 15 ml). The combined extracts were dried over sodium sulfate, filtered and concentrated to give a red solid. The products were recrystallized from ethanol, at ambient temperature and in air, to give light yellow crystals suitable for single-crystal X-ray diffraction. Compound (I) (R = H): yield 77%. m.p. 510–511 K; MS (70 eV) m/z (%) 465/463 (25/71, M+2/M), 450/448 (36/100), 435/433 (9/26), 422/420 (7/20); HRMS m/z found 463.1469, C₂₉H₂₂ClN₃O requires m/z = 463.1451. Compound (II) (R = OMe), yield 75%, m.p. 503–504 K: MS: (70 eV) m/z (%) 495/493 (28/80, M+2/M), 480/478 (30/100), 465/463 (11/37), 452/450 (10/29); HRMS m/z found 493.1544, C₃₀H₂₄ClN₃O₂ requires m/z = 493.1557.

S3. Refinement

All H atoms were located in difference maps and then treated as riding atoms in geometrically idealized positions, with C—H distances of 0.95 (aromatic) or 0.98 Å (methyl), and with U_iso(U) = kU_eq(C), where k = 1.5 for the methyl groups, which were permitted to rotate but not to tilt, and 1.2 otherwise.

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: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures

	Fig. 1. The molecular structure of compound (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The structures of the two independent molecules of compound (II), showing the atom-labelling scheme for (a) a type 1 molecule and (b) a type 2 molecule. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 3. A stereoview of part of the crystal structure of compound (I), showing the formation of a π-stacked chain of hydrogen-bonded dimers along [001]. For the sake of clarity, H atoms not involved in the motif shown have been omitted.
	Fig. 4. A stereoview of part of the crystal structure of compound (II), showing the formation of a hydrogen-bonded chain of rings along [110]. For the sake of clarity, H atoms not involved in the motifs shown have been omitted.
	Fig. 5. Part of the crystal structure of compound (II), showing the π–π stacking interaction between pairs of type 2 molecules. For the sake of clarity, H atoms have all been omitted. Atoms marked with an asterisk (*) are at the symmetry position (-x+1, -y+1, -z+1).

(I) 3-tert-butyl-1-(4-chlorophenyl)-4- phenylindeno[1,2-b]pyrazolo[4,3-e]pyridin-5(1H)-one

Crystal data

C29H22ClN3O	Z = 2
Mr = 463.95	F(000) = 484
Triclinic, P1	Dx = 1.336 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1014 (5) Å	Cell parameters from 5311 reflections
b = 11.3554 (10) Å	θ = 3.0–27.5°
c = 13.5762 (11) Å	µ = 0.19 mm^−1
α = 102.755 (7)°	T = 120 K
β = 90.013 (8)°	Block, yellow
γ = 108.268 (7)°	0.43 × 0.22 × 0.16 mm
V = 1153.47 (16) Å^3

Data collection

Bruker–Nonius KappaCCD diffractometer	5310 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	4065 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −14→14
Tmin = 0.921, Tmax = 0.970	l = −17→17
29371 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.098	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.034P)^2 + 0.6438P] where P = (Fo^2 + 2Fc^2)/3
5310 reflections	(Δ/σ)max = 0.001
310 parameters	Δρmax = 0.22 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
N1	1.02625 (16)	0.70513 (12)	0.52904 (9)	0.0174 (3)
N2	1.11894 (17)	0.80399 (12)	0.60701 (10)	0.0194 (3)
C3	1.0432 (2)	0.78827 (15)	0.69158 (12)	0.0186 (3)
C3A	0.8913 (2)	0.67420 (14)	0.67044 (11)	0.0169 (3)
C4	0.7534 (2)	0.60694 (15)	0.72231 (11)	0.0178 (3)
C4A	0.6384 (2)	0.49531 (15)	0.66349 (11)	0.0180 (3)
C5	0.4793 (2)	0.40028 (15)	0.68971 (12)	0.0202 (3)
C5A	0.4119 (2)	0.30062 (15)	0.59350 (12)	0.0187 (3)
C6	0.2704 (2)	0.18974 (15)	0.57584 (13)	0.0222 (3)
H6	0.1999	0.1665	0.6288	0.027*
C7	0.2351 (2)	0.11339 (16)	0.47773 (13)	0.0238 (4)
H7	0.1386	0.0370	0.4634	0.029*
C8	0.3394 (2)	0.14757 (15)	0.40026 (13)	0.0227 (3)
H8	0.3126	0.0941	0.3339	0.027*
C9	0.4824 (2)	0.25901 (15)	0.41851 (12)	0.0196 (3)
H9	0.5536	0.2822	0.3658	0.024*
C9A	0.51688 (19)	0.33451 (14)	0.51606 (12)	0.0172 (3)
C9B	0.65699 (19)	0.45486 (14)	0.55882 (11)	0.0166 (3)
N10	0.77787 (16)	0.51619 (12)	0.50610 (10)	0.0174 (3)
C10A	0.88979 (19)	0.62382 (14)	0.56436 (11)	0.0162 (3)
C11	1.07391 (19)	0.70754 (14)	0.42839 (11)	0.0172 (3)
C12	0.9708 (2)	0.62101 (16)	0.34494 (12)	0.0215 (3)
H12	0.8713	0.5542	0.3545	0.026*
C13	1.0137 (2)	0.63248 (16)	0.24773 (12)	0.0237 (4)
H13	0.9425	0.5744	0.1907	0.028*
C14	1.1601 (2)	0.72867 (16)	0.23410 (12)	0.0228 (3)
Cl14	1.20917 (6)	0.74609 (5)	0.11228 (3)	0.03335 (13)
C15	1.2674 (2)	0.81194 (16)	0.31660 (13)	0.0230 (3)
H15	1.3704	0.8756	0.3065	0.028*
C16	1.2239 (2)	0.80201 (15)	0.41393 (12)	0.0204 (3)
H16	1.2963	0.8596	0.4707	0.024*
C31	1.1282 (2)	0.88690 (16)	0.78844 (12)	0.0225 (3)
C32	1.3107 (2)	0.96804 (17)	0.76897 (13)	0.0260 (4)
H32A	1.3009	1.0128	0.7164	0.039*
H32B	1.3816	0.9127	0.7465	0.039*
H32C	1.3661	1.0304	0.8316	0.039*
C33	1.0198 (2)	0.97662 (18)	0.82136 (15)	0.0350 (4)
H33A	0.9038	0.9274	0.8367	0.052*
H33B	1.0082	1.0176	0.7665	0.052*
H33C	1.0782	1.0420	0.8819	0.052*
C34	1.1488 (3)	0.8224 (2)	0.87339 (14)	0.0388 (5)
H34A	1.2138	0.7629	0.8504	0.058*
H34B	1.0335	0.7757	0.8913	0.058*
H34C	1.2125	0.8873	0.9329	0.058*
C41	0.7185 (2)	0.64766 (15)	0.83053 (11)	0.0191 (3)
C42	0.6362 (2)	0.73944 (16)	0.85842 (12)	0.0231 (3)
H42	0.6110	0.7813	0.8098	0.028*
C43	0.5908 (2)	0.77002 (17)	0.95746 (13)	0.0274 (4)
H43	0.5355	0.8332	0.9764	0.033*
C44	0.6260 (2)	0.70857 (17)	1.02828 (12)	0.0267 (4)
H44	0.5954	0.7299	1.0959	0.032*
C45	0.7058 (2)	0.61610 (17)	1.00049 (12)	0.0256 (4)
H45	0.7292	0.5734	1.0490	0.031*
C46	0.7516 (2)	0.58556 (16)	0.90190 (12)	0.0237 (4)
H46	0.8060	0.5218	0.8831	0.028*
O5	0.41358 (15)	0.40214 (12)	0.77009 (9)	0.0282 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0163 (6)	0.0172 (6)	0.0169 (6)	0.0031 (5)	0.0029 (5)	0.0036 (5)
N2	0.0187 (7)	0.0197 (7)	0.0180 (7)	0.0049 (5)	0.0007 (5)	0.0028 (5)
C3	0.0172 (7)	0.0201 (8)	0.0189 (8)	0.0065 (6)	0.0023 (6)	0.0048 (6)
C3A	0.0191 (7)	0.0185 (7)	0.0149 (7)	0.0081 (6)	0.0025 (6)	0.0048 (6)
C4	0.0190 (8)	0.0211 (8)	0.0165 (7)	0.0094 (6)	0.0027 (6)	0.0065 (6)
C4A	0.0176 (7)	0.0214 (8)	0.0179 (7)	0.0083 (6)	0.0042 (6)	0.0077 (6)
C5	0.0180 (8)	0.0239 (8)	0.0216 (8)	0.0076 (7)	0.0033 (6)	0.0097 (7)
C5A	0.0178 (7)	0.0213 (8)	0.0202 (8)	0.0087 (6)	0.0025 (6)	0.0076 (6)
C6	0.0189 (8)	0.0229 (8)	0.0290 (9)	0.0080 (7)	0.0069 (7)	0.0129 (7)
C7	0.0196 (8)	0.0182 (8)	0.0324 (9)	0.0046 (7)	0.0021 (7)	0.0055 (7)
C8	0.0224 (8)	0.0198 (8)	0.0251 (8)	0.0074 (7)	0.0014 (7)	0.0026 (7)
C9	0.0199 (8)	0.0194 (8)	0.0214 (8)	0.0074 (6)	0.0034 (6)	0.0069 (6)
C9A	0.0159 (7)	0.0172 (7)	0.0213 (8)	0.0075 (6)	0.0029 (6)	0.0067 (6)
C9B	0.0172 (7)	0.0182 (7)	0.0171 (7)	0.0083 (6)	0.0024 (6)	0.0056 (6)
N10	0.0174 (6)	0.0177 (6)	0.0189 (6)	0.0069 (5)	0.0042 (5)	0.0063 (5)
C10A	0.0154 (7)	0.0174 (7)	0.0180 (7)	0.0067 (6)	0.0036 (6)	0.0063 (6)
C11	0.0168 (7)	0.0197 (8)	0.0184 (7)	0.0085 (6)	0.0060 (6)	0.0074 (6)
C12	0.0175 (8)	0.0251 (8)	0.0212 (8)	0.0050 (7)	0.0054 (6)	0.0065 (7)
C13	0.0221 (8)	0.0310 (9)	0.0182 (8)	0.0092 (7)	0.0042 (6)	0.0049 (7)
C14	0.0249 (8)	0.0306 (9)	0.0202 (8)	0.0145 (7)	0.0096 (7)	0.0124 (7)
Cl14	0.0376 (3)	0.0441 (3)	0.0229 (2)	0.0134 (2)	0.01290 (18)	0.01654 (19)
C15	0.0218 (8)	0.0217 (8)	0.0281 (9)	0.0073 (7)	0.0094 (7)	0.0104 (7)
C16	0.0196 (8)	0.0203 (8)	0.0231 (8)	0.0077 (7)	0.0040 (6)	0.0069 (6)
C31	0.0211 (8)	0.0239 (8)	0.0177 (8)	0.0029 (7)	0.0018 (6)	0.0018 (7)
C32	0.0215 (8)	0.0276 (9)	0.0232 (8)	0.0031 (7)	0.0012 (7)	0.0012 (7)
C33	0.0247 (9)	0.0320 (10)	0.0369 (10)	0.0055 (8)	0.0043 (8)	−0.0098 (8)
C34	0.0380 (11)	0.0435 (12)	0.0246 (10)	−0.0045 (9)	−0.0080 (8)	0.0126 (9)
C41	0.0173 (7)	0.0228 (8)	0.0154 (7)	0.0038 (6)	0.0036 (6)	0.0048 (6)
C42	0.0235 (8)	0.0264 (9)	0.0206 (8)	0.0090 (7)	0.0035 (6)	0.0063 (7)
C43	0.0301 (9)	0.0302 (9)	0.0232 (9)	0.0134 (8)	0.0068 (7)	0.0035 (7)
C44	0.0271 (9)	0.0306 (9)	0.0167 (8)	0.0038 (7)	0.0072 (7)	0.0021 (7)
C45	0.0279 (9)	0.0298 (9)	0.0187 (8)	0.0058 (7)	0.0022 (7)	0.0095 (7)
C46	0.0254 (9)	0.0264 (9)	0.0206 (8)	0.0094 (7)	0.0042 (7)	0.0067 (7)
O5	0.0247 (6)	0.0369 (7)	0.0196 (6)	0.0030 (5)	0.0079 (5)	0.0093 (5)

Geometric parameters (Å, º)

N1—C10A	1.3640 (19)	C13—C14	1.382 (2)
N1—N2	1.3752 (18)	C13—H13	0.9500
N1—C11	1.4237 (19)	C14—C15	1.386 (2)
N2—C3	1.3223 (19)	C14—Cl14	1.7402 (16)
C3—C3A	1.453 (2)	C15—C16	1.387 (2)
C3—C31	1.524 (2)	C15—H15	0.9500
C3A—C4	1.425 (2)	C16—H16	0.9500
C3A—C10A	1.426 (2)	C31—C34	1.531 (2)
C4—C4A	1.388 (2)	C31—C32	1.536 (2)
C4—C41	1.495 (2)	C31—C33	1.539 (2)
C4A—C9B	1.417 (2)	C32—H32A	0.9800
C4A—C5	1.500 (2)	C32—H32B	0.9800
C5—O5	1.2133 (18)	C32—H32C	0.9800
C5—C5A	1.498 (2)	C33—H33A	0.9800
C5A—C6	1.385 (2)	C33—H33B	0.9800
C5A—C9A	1.397 (2)	C33—H33C	0.9800
C6—C7	1.394 (2)	C34—H34A	0.9800
C6—H6	0.9500	C34—H34B	0.9800
C7—C8	1.395 (2)	C34—H34C	0.9800
C7—H7	0.9500	C41—C46	1.389 (2)
C8—C9	1.395 (2)	C41—C42	1.391 (2)
C8—H8	0.9500	C42—C43	1.392 (2)
C9—C9A	1.384 (2)	C42—H42	0.9500
C9—H9	0.9500	C43—C44	1.383 (2)
C9A—C9B	1.473 (2)	C43—H43	0.9500
C9B—N10	1.3225 (19)	C44—C45	1.383 (2)
N10—C10A	1.349 (2)	C44—H44	0.9500
C11—C12	1.393 (2)	C45—C46	1.388 (2)
C11—C16	1.393 (2)	C45—H45	0.9500
C12—C13	1.388 (2)	C46—H46	0.9500
C12—H12	0.9500
C10A—N1—N2	110.46 (12)	C12—C13—H13	120.1
C10A—N1—C11	130.76 (13)	C13—C14—C15	120.63 (15)
N2—N1—C11	118.55 (12)	C13—C14—Cl14	119.68 (13)
C3—N2—N1	108.25 (12)	C15—C14—Cl14	119.68 (13)
N2—C3—C3A	109.96 (13)	C14—C15—C16	119.73 (15)
N2—C3—C31	116.82 (13)	C14—C15—H15	120.1
C3A—C3—C31	133.21 (14)	C16—C15—H15	120.1
C4—C3A—C10A	116.95 (14)	C15—C16—C11	119.97 (15)
C4—C3A—C3	139.19 (14)	C15—C16—H16	120.0
C10A—C3A—C3	103.84 (13)	C11—C16—H16	120.0
C4A—C4—C3A	115.22 (14)	C3—C31—C34	111.04 (14)
C4A—C4—C41	118.19 (13)	C3—C31—C32	109.51 (13)
C3A—C4—C41	126.54 (14)	C34—C31—C32	107.80 (14)
C4—C4A—C9B	121.36 (14)	C3—C31—C33	110.11 (14)
C4—C4A—C5	131.04 (14)	C34—C31—C33	110.35 (15)
C9B—C4A—C5	107.57 (13)	C32—C31—C33	107.95 (14)
O5—C5—C5A	125.87 (15)	C31—C32—H32A	109.5
O5—C5—C4A	128.74 (15)	C31—C32—H32B	109.5
C5A—C5—C4A	105.37 (13)	H32A—C32—H32B	109.5
C6—C5A—C9A	121.31 (15)	C31—C32—H32C	109.5
C6—C5A—C5	129.46 (14)	H32A—C32—H32C	109.5
C9A—C5A—C5	109.23 (13)	H32B—C32—H32C	109.5
C5A—C6—C7	117.73 (15)	C31—C33—H33A	109.5
C5A—C6—H6	121.1	C31—C33—H33B	109.5
C7—C6—H6	121.1	H33A—C33—H33B	109.5
C6—C7—C8	120.97 (15)	C31—C33—H33C	109.5
C6—C7—H7	119.5	H33A—C33—H33C	109.5
C8—C7—H7	119.5	H33B—C33—H33C	109.5
C7—C8—C9	121.12 (15)	C31—C34—H34A	109.5
C7—C8—H8	119.4	C31—C34—H34B	109.5
C9—C8—H8	119.4	H34A—C34—H34B	109.5
C9A—C9—C8	117.70 (15)	C31—C34—H34C	109.5
C9A—C9—H9	121.2	H34A—C34—H34C	109.5
C8—C9—H9	121.2	H34B—C34—H34C	109.5
C9—C9A—C5A	121.18 (14)	C46—C41—C42	119.31 (14)
C9—C9A—C9B	130.47 (14)	C46—C41—C4	120.38 (14)
C5A—C9A—C9B	108.35 (13)	C42—C41—C4	120.00 (14)
N10—C9B—C4A	125.90 (14)	C41—C42—C43	120.10 (16)
N10—C9B—C9A	124.64 (14)	C41—C42—H42	120.0
C4A—C9B—C9A	109.44 (13)	C43—C42—H42	120.0
C9B—N10—C10A	112.11 (13)	C44—C43—C42	120.15 (16)
N10—C10A—N1	124.18 (13)	C44—C43—H43	119.9
N10—C10A—C3A	128.35 (14)	C42—C43—H43	119.9
N1—C10A—C3A	107.47 (13)	C45—C44—C43	119.91 (15)
C12—C11—C16	119.83 (14)	C45—C44—H44	120.0
C12—C11—N1	121.46 (13)	C43—C44—H44	120.0
C16—C11—N1	118.67 (14)	C44—C45—C46	120.11 (16)
C13—C12—C11	119.92 (15)	C44—C45—H45	119.9
C13—C12—H12	120.0	C46—C45—H45	119.9
C11—C12—H12	120.0	C45—C46—C41	120.41 (16)
C14—C13—C12	119.84 (16)	C45—C46—H46	119.8
C14—C13—H13	120.1	C41—C46—H46	119.8
C10A—N1—N2—C3	−0.66 (17)	C9A—C9B—N10—C10A	179.97 (13)
C11—N1—N2—C3	174.40 (13)	C9B—N10—C10A—N1	−179.73 (14)
N1—N2—C3—C3A	−0.45 (17)	C9B—N10—C10A—C3A	0.5 (2)
N1—N2—C3—C31	178.79 (13)	N2—N1—C10A—N10	−178.30 (13)
N2—C3—C3A—C4	−176.85 (18)	C11—N1—C10A—N10	7.4 (2)
C31—C3—C3A—C4	4.1 (3)	N2—N1—C10A—C3A	1.50 (16)
N2—C3—C3A—C10A	1.31 (17)	C11—N1—C10A—C3A	−172.77 (14)
C31—C3—C3A—C10A	−177.76 (16)	C4—C3A—C10A—N10	−3.2 (2)
C10A—C3A—C4—C4A	3.4 (2)	C3—C3A—C10A—N10	178.13 (14)
C3—C3A—C4—C4A	−178.58 (17)	C4—C3A—C10A—N1	176.99 (13)
C10A—C3A—C4—C41	−173.94 (14)	C3—C3A—C10A—N1	−1.66 (16)
C3—C3A—C4—C41	4.1 (3)	C10A—N1—C11—C12	3.3 (2)
C3A—C4—C4A—C9B	−1.6 (2)	N2—N1—C11—C12	−170.54 (14)
C41—C4—C4A—C9B	176.05 (14)	C10A—N1—C11—C16	−179.09 (15)
C3A—C4—C4A—C5	−179.59 (15)	N2—N1—C11—C16	7.0 (2)
C41—C4—C4A—C5	−2.0 (2)	C16—C11—C12—C13	−2.7 (2)
C4—C4A—C5—O5	1.5 (3)	N1—C11—C12—C13	174.81 (14)
C9B—C4A—C5—O5	−176.75 (16)	C11—C12—C13—C14	1.0 (2)
C4—C4A—C5—C5A	−179.94 (15)	C12—C13—C14—C15	1.7 (2)
C9B—C4A—C5—C5A	1.81 (16)	C12—C13—C14—Cl14	−177.80 (13)
O5—C5—C5A—C6	−3.2 (3)	C13—C14—C15—C16	−2.6 (2)
C4A—C5—C5A—C6	178.18 (15)	Cl14—C14—C15—C16	176.91 (12)
O5—C5—C5A—C9A	176.85 (16)	C14—C15—C16—C11	0.8 (2)
C4A—C5—C5A—C9A	−1.76 (17)	C12—C11—C16—C15	1.8 (2)
C9A—C5A—C6—C7	−0.6 (2)	N1—C11—C16—C15	−175.77 (14)
C5—C5A—C6—C7	179.46 (15)	N2—C3—C31—C34	−131.81 (16)
C5A—C6—C7—C8	0.2 (2)	C3A—C3—C31—C34	47.2 (2)
C6—C7—C8—C9	0.1 (2)	N2—C3—C31—C32	−12.9 (2)
C7—C8—C9—C9A	−0.1 (2)	C3A—C3—C31—C32	166.15 (16)
C8—C9—C9A—C5A	−0.2 (2)	N2—C3—C31—C33	105.68 (17)
C8—C9—C9A—C9B	179.16 (15)	C3A—C3—C31—C33	−75.3 (2)
C6—C5A—C9A—C9	0.6 (2)	C4A—C4—C41—C46	75.0 (2)
C5—C5A—C9A—C9	−179.44 (14)	C3A—C4—C41—C46	−107.65 (19)
C6—C5A—C9A—C9B	−178.90 (14)	C4A—C4—C41—C42	−98.47 (18)
C5—C5A—C9A—C9B	1.05 (17)	C3A—C4—C41—C42	78.8 (2)
C4—C4A—C9B—N10	−1.3 (2)	C46—C41—C42—C43	1.2 (2)
C5—C4A—C9B—N10	177.16 (14)	C4—C41—C42—C43	174.77 (15)
C4—C4A—C9B—C9A	−179.69 (14)	C41—C42—C43—C44	−0.5 (3)
C5—C4A—C9B—C9A	−1.24 (17)	C42—C43—C44—C45	−0.3 (3)
C9—C9A—C9B—N10	2.3 (3)	C43—C44—C45—C46	0.5 (3)
C5A—C9A—C9B—N10	−178.29 (14)	C44—C45—C46—C41	0.2 (3)
C9—C9A—C9B—C4A	−179.32 (15)	C42—C41—C46—C45	−1.0 (2)
C5A—C9A—C9B—C4A	0.13 (17)	C4—C41—C46—C45	−174.60 (15)
C4A—C9B—N10—C10A	1.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C44—H44···O5^i	0.95	2.59	3.232 (2)	125

Symmetry code: (i) −x+1, −y+1, −z+2.

(II) 3-tert-butyl-1-(4-chlorophenyl)-4- (4-methoxyphenyl)indeno[1,2-b]pyrazolo[4,3-e]pyridin-5(1H)-one

Crystal data

C30H24ClN3O2	Z = 4
Mr = 493.97	F(000) = 1032
Triclinic, P1	Dx = 1.358 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.1911 (9) Å	Cell parameters from 11085 reflections
b = 11.4258 (8) Å	θ = 3.0–27.5°
c = 20.095 (2) Å	µ = 0.19 mm^−1
α = 97.411 (6)°	T = 120 K
β = 93.272 (7)°	Block, yellow
γ = 107.635 (6)°	0.42 × 0.30 × 0.29 mm
V = 2415.7 (4) Å^3

Data collection

Bruker–Nonius KappaCCD diffractometer	11085 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	7328 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ϕ and ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −14→14
Tmin = 0.924, Tmax = 0.946	l = −26→26
63410 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0383P)^2 + 1.5471P] where P = (Fo^2 + 2Fc^2)/3
11085 reflections	(Δ/σ)max = 0.001
657 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

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

	x	y	z	Uiso*/Ueq
N11	0.56735 (15)	0.29090 (15)	0.07001 (8)	0.0218 (4)
N12	0.46516 (15)	0.22309 (15)	0.02484 (8)	0.0229 (4)
C13	0.39573 (18)	0.13181 (18)	0.05363 (10)	0.0208 (4)
C13A	0.45258 (18)	0.13760 (18)	0.12131 (10)	0.0202 (4)
C14	0.43084 (18)	0.06972 (18)	0.17645 (10)	0.0212 (4)
C14A	0.51871 (18)	0.11965 (18)	0.23286 (10)	0.0211 (4)
C15	0.53088 (18)	0.07236 (18)	0.29793 (10)	0.0219 (4)
C15A	0.64932 (18)	0.16126 (18)	0.33651 (10)	0.0223 (4)
C16	0.7073 (2)	0.1574 (2)	0.39844 (11)	0.0263 (5)
H16	0.6707	0.0939	0.4242	0.032*
C17	0.8208 (2)	0.2492 (2)	0.42176 (11)	0.0279 (5)
H17	0.8630	0.2482	0.4639	0.033*
C18	0.8730 (2)	0.3423 (2)	0.38429 (11)	0.0272 (5)
H18	0.9504	0.4043	0.4015	0.033*
C19	0.81465 (19)	0.34693 (19)	0.32199 (10)	0.0236 (4)
H19	0.8505	0.4112	0.2966	0.028*
C19A	0.70208 (18)	0.25398 (18)	0.29840 (10)	0.0211 (4)
C19B	0.62271 (18)	0.22842 (18)	0.23356 (10)	0.0206 (4)
N110	0.64826 (15)	0.29262 (15)	0.18321 (8)	0.0213 (4)
C110	0.56192 (18)	0.24340 (18)	0.12891 (10)	0.0209 (4)
C111	0.66203 (19)	0.38911 (18)	0.04842 (10)	0.0211 (4)
C112	0.7847 (2)	0.4315 (2)	0.07960 (11)	0.0277 (5)
H112	0.8072	0.3949	0.1162	0.033*
C113	0.8739 (2)	0.5274 (2)	0.05709 (11)	0.0281 (5)
H113	0.9577	0.5573	0.0785	0.034*
C114	0.84072 (19)	0.57909 (19)	0.00358 (11)	0.0245 (5)
Cl14	0.95510 (5)	0.69863 (5)	−0.02428 (3)	0.03492 (14)
C115	0.7195 (2)	0.5371 (2)	−0.02799 (11)	0.0276 (5)
H115	0.6978	0.5733	−0.0650	0.033*
C116	0.6295 (2)	0.44192 (19)	−0.00538 (10)	0.0251 (5)
H116	0.5457	0.4129	−0.0267	0.030*
C131	0.27873 (18)	0.04187 (19)	0.01135 (10)	0.0233 (4)
C132	0.2536 (2)	0.0929 (2)	−0.05300 (11)	0.0323 (5)
H13A	0.2451	0.1757	−0.0410	0.048*
H13B	0.1756	0.0372	−0.0786	0.048*
H13C	0.3240	0.0986	−0.0806	0.048*
C133	0.3003 (2)	−0.0832 (2)	−0.00877 (12)	0.0327 (5)
H13D	0.3760	−0.0708	−0.0327	0.049*
H13E	0.2273	−0.1393	−0.0383	0.049*
H13F	0.3115	−0.1195	0.0318	0.049*
C134	0.16281 (19)	0.0254 (2)	0.05084 (11)	0.0295 (5)
H13G	0.1768	−0.0077	0.0922	0.044*
H13H	0.0886	−0.0326	0.0230	0.044*
H13I	0.1491	0.1059	0.0625	0.044*
C141	0.32811 (18)	−0.04872 (18)	0.17933 (10)	0.0210 (4)
C142	0.34209 (19)	−0.16257 (19)	0.15461 (11)	0.0256 (5)
H142	0.4120	−0.1648	0.1304	0.031*
C143	0.25517 (19)	−0.27316 (19)	0.16482 (11)	0.0272 (5)
H143	0.2658	−0.3505	0.1477	0.033*
C144	0.15299 (18)	−0.27030 (18)	0.20006 (11)	0.0232 (4)
C145	0.13599 (19)	−0.15711 (19)	0.22340 (11)	0.0245 (5)
H145	0.0640	−0.1552	0.2458	0.029*
C146	0.22390 (18)	−0.04713 (19)	0.21404 (10)	0.0235 (4)
H146	0.2133	0.0301	0.2314	0.028*
O144	0.06442 (13)	−0.37368 (13)	0.21522 (8)	0.0314 (4)
C147	0.0924 (2)	−0.4879 (2)	0.20332 (13)	0.0343 (5)
H14A	0.0931	−0.5117	0.1548	0.052*
H14B	0.0280	−0.5529	0.2205	0.052*
H14C	0.1752	−0.4775	0.2265	0.052*
O15	0.46228 (13)	−0.01917 (13)	0.31718 (7)	0.0289 (3)
N21	0.41570 (15)	0.41471 (15)	0.29199 (8)	0.0206 (4)
N22	0.45913 (15)	0.49317 (15)	0.24625 (8)	0.0215 (4)
C23	0.57028 (18)	0.57217 (18)	0.27160 (10)	0.0192 (4)
C23A	0.60364 (18)	0.54681 (18)	0.33813 (10)	0.0191 (4)
C24	0.70349 (18)	0.59396 (18)	0.39119 (10)	0.0197 (4)
C24A	0.69021 (18)	0.52704 (18)	0.44453 (10)	0.0199 (4)
C25	0.77463 (19)	0.54600 (19)	0.50847 (10)	0.0237 (4)
C25A	0.71036 (18)	0.44324 (19)	0.54602 (10)	0.0223 (4)
C26	0.7481 (2)	0.4161 (2)	0.60764 (10)	0.0258 (5)
H26	0.8246	0.4667	0.6331	0.031*
C27	0.6708 (2)	0.3127 (2)	0.63098 (11)	0.0282 (5)
H27	0.6943	0.2926	0.6732	0.034*
C28	0.5592 (2)	0.2381 (2)	0.59319 (11)	0.0270 (5)
H28	0.5083	0.1670	0.6095	0.032*
C29	0.52149 (19)	0.26675 (19)	0.53164 (10)	0.0247 (5)
H29	0.4449	0.2165	0.5061	0.030*
C29A	0.59773 (18)	0.36952 (19)	0.50863 (10)	0.0213 (4)
C29B	0.58416 (18)	0.42161 (18)	0.44612 (10)	0.0192 (4)
N210	0.48715 (15)	0.37700 (15)	0.39927 (8)	0.0201 (4)
C210	0.50089 (18)	0.44282 (18)	0.34759 (10)	0.0198 (4)
C211	0.29240 (18)	0.32774 (18)	0.27826 (10)	0.0203 (4)
C212	0.22507 (18)	0.27967 (19)	0.32998 (10)	0.0235 (4)
H212	0.2638	0.2998	0.3751	0.028*
C213	0.10145 (19)	0.20230 (19)	0.31581 (11)	0.0260 (5)
H213	0.0553	0.1695	0.3511	0.031*
C214	0.04602 (18)	0.17333 (18)	0.25011 (11)	0.0242 (4)
Cl24	−0.10857 (5)	0.07462 (6)	0.23252 (3)	0.03698 (15)
C215	0.11179 (19)	0.21924 (19)	0.19823 (11)	0.0245 (5)
H215	0.0725	0.1982	0.1533	0.029*
C216	0.23593 (19)	0.29643 (19)	0.21189 (10)	0.0230 (4)
H216	0.2820	0.3277	0.1763	0.028*
C231	0.63711 (18)	0.66646 (19)	0.22811 (10)	0.0215 (4)
C232	0.5705 (2)	0.6280 (2)	0.15604 (10)	0.0257 (5)
H23A	0.5692	0.5434	0.1388	0.039*
H23B	0.6160	0.6853	0.1269	0.039*
H23C	0.4839	0.6309	0.1564	0.039*
C233	0.6289 (2)	0.79539 (19)	0.25499 (11)	0.0291 (5)
H23D	0.5404	0.7905	0.2573	0.044*
H23E	0.6667	0.8540	0.2247	0.044*
H23F	0.6745	0.8241	0.3001	0.044*
C234	0.77494 (19)	0.6702 (2)	0.22475 (11)	0.0325 (5)
H23G	0.8222	0.7052	0.2691	0.049*
H23H	0.8122	0.7222	0.1914	0.049*
H23I	0.7783	0.5858	0.2116	0.049*
C241	0.81715 (18)	0.70594 (18)	0.39442 (10)	0.0197 (4)
C242	0.80933 (19)	0.82528 (19)	0.41020 (10)	0.0243 (4)
H242	0.7296	0.8363	0.4160	0.029*
C243	0.9160 (2)	0.92818 (19)	0.41757 (11)	0.0267 (5)
H243	0.9092	1.0092	0.4282	0.032*
C244	1.03293 (19)	0.91287 (18)	0.40936 (10)	0.0231 (4)
C245	1.04326 (19)	0.79517 (19)	0.39425 (10)	0.0243 (5)
H245	1.1231	0.7843	0.3886	0.029*
C246	0.93508 (18)	0.69277 (19)	0.38738 (10)	0.0234 (4)
H246	0.9422	0.6117	0.3776	0.028*
O244	1.13345 (13)	1.02023 (13)	0.41752 (8)	0.0312 (4)
C247	1.2541 (2)	1.0084 (2)	0.40632 (12)	0.0349 (5)
H24A	1.2811	0.9672	0.4415	0.052*
H24B	1.3152	1.0911	0.4077	0.052*
H24C	1.2490	0.9589	0.3620	0.052*
O25	0.87457 (13)	0.62675 (14)	0.52722 (7)	0.0320 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0199 (9)	0.0224 (9)	0.0183 (9)	0.0003 (7)	−0.0036 (7)	0.0034 (7)
N12	0.0190 (9)	0.0236 (9)	0.0222 (9)	0.0026 (7)	−0.0034 (7)	0.0015 (7)
C13	0.0198 (10)	0.0216 (10)	0.0205 (11)	0.0062 (8)	−0.0003 (8)	0.0033 (8)
C13A	0.0178 (10)	0.0186 (10)	0.0220 (11)	0.0040 (8)	0.0004 (8)	0.0003 (8)
C14	0.0192 (10)	0.0208 (10)	0.0241 (11)	0.0068 (8)	0.0032 (8)	0.0034 (9)
C14A	0.0179 (10)	0.0218 (10)	0.0228 (11)	0.0045 (8)	0.0013 (8)	0.0046 (9)
C15	0.0196 (10)	0.0229 (11)	0.0253 (11)	0.0082 (8)	0.0038 (8)	0.0064 (9)
C15A	0.0214 (10)	0.0226 (10)	0.0231 (11)	0.0074 (8)	0.0021 (8)	0.0031 (9)
C16	0.0293 (12)	0.0284 (11)	0.0234 (11)	0.0108 (9)	0.0027 (9)	0.0077 (9)
C17	0.0304 (12)	0.0322 (12)	0.0226 (11)	0.0136 (10)	−0.0042 (9)	0.0037 (9)
C18	0.0262 (11)	0.0270 (11)	0.0257 (12)	0.0069 (9)	−0.0045 (9)	0.0011 (9)
C19	0.0223 (11)	0.0228 (11)	0.0241 (11)	0.0052 (9)	−0.0004 (8)	0.0041 (9)
C19A	0.0212 (10)	0.0229 (10)	0.0186 (10)	0.0071 (8)	0.0003 (8)	0.0014 (8)
C19B	0.0211 (10)	0.0194 (10)	0.0208 (11)	0.0061 (8)	0.0003 (8)	0.0025 (8)
N110	0.0212 (9)	0.0224 (9)	0.0183 (9)	0.0042 (7)	−0.0008 (7)	0.0035 (7)
C110	0.0202 (10)	0.0217 (10)	0.0194 (10)	0.0043 (8)	0.0003 (8)	0.0040 (8)
C111	0.0237 (10)	0.0183 (10)	0.0198 (11)	0.0045 (8)	0.0016 (8)	0.0028 (8)
C112	0.0266 (11)	0.0304 (12)	0.0245 (12)	0.0052 (9)	−0.0030 (9)	0.0104 (10)
C113	0.0251 (11)	0.0284 (12)	0.0275 (12)	0.0025 (9)	−0.0006 (9)	0.0077 (10)
C114	0.0264 (11)	0.0200 (10)	0.0255 (11)	0.0037 (9)	0.0065 (9)	0.0041 (9)
Cl14	0.0327 (3)	0.0294 (3)	0.0399 (3)	0.0013 (2)	0.0065 (2)	0.0147 (3)
C115	0.0315 (12)	0.0291 (12)	0.0216 (11)	0.0067 (10)	0.0005 (9)	0.0096 (9)
C116	0.0242 (11)	0.0265 (11)	0.0221 (11)	0.0048 (9)	−0.0013 (9)	0.0039 (9)
C131	0.0194 (10)	0.0253 (11)	0.0220 (11)	0.0040 (8)	−0.0027 (8)	0.0016 (9)
C132	0.0285 (12)	0.0373 (13)	0.0224 (12)	−0.0003 (10)	−0.0064 (9)	0.0027 (10)
C133	0.0272 (12)	0.0278 (12)	0.0363 (13)	0.0037 (10)	−0.0036 (10)	−0.0042 (10)
C134	0.0201 (11)	0.0367 (13)	0.0274 (12)	0.0047 (9)	−0.0030 (9)	0.0020 (10)
C141	0.0192 (10)	0.0230 (10)	0.0198 (10)	0.0041 (8)	−0.0014 (8)	0.0067 (8)
C142	0.0199 (10)	0.0272 (11)	0.0296 (12)	0.0068 (9)	0.0042 (9)	0.0042 (9)
C143	0.0250 (11)	0.0204 (11)	0.0344 (13)	0.0062 (9)	0.0022 (9)	0.0007 (9)
C144	0.0194 (10)	0.0214 (10)	0.0259 (11)	0.0009 (8)	−0.0021 (8)	0.0081 (9)
C145	0.0193 (10)	0.0280 (11)	0.0268 (12)	0.0066 (9)	0.0038 (8)	0.0071 (9)
C146	0.0231 (11)	0.0225 (10)	0.0244 (11)	0.0064 (9)	0.0012 (9)	0.0037 (9)
O144	0.0259 (8)	0.0223 (8)	0.0430 (10)	0.0015 (6)	0.0058 (7)	0.0074 (7)
C147	0.0367 (13)	0.0217 (11)	0.0416 (14)	0.0034 (10)	0.0030 (11)	0.0087 (10)
O15	0.0267 (8)	0.0287 (8)	0.0304 (9)	0.0044 (7)	0.0023 (6)	0.0122 (7)
N21	0.0183 (8)	0.0229 (9)	0.0181 (9)	0.0016 (7)	−0.0006 (7)	0.0073 (7)
N22	0.0218 (9)	0.0232 (9)	0.0188 (9)	0.0044 (7)	0.0019 (7)	0.0066 (7)
C23	0.0186 (10)	0.0205 (10)	0.0181 (10)	0.0056 (8)	0.0002 (8)	0.0035 (8)
C23A	0.0190 (10)	0.0195 (10)	0.0191 (10)	0.0055 (8)	0.0026 (8)	0.0046 (8)
C24	0.0189 (10)	0.0207 (10)	0.0195 (10)	0.0067 (8)	0.0017 (8)	0.0026 (8)
C24A	0.0165 (10)	0.0235 (10)	0.0185 (10)	0.0047 (8)	−0.0007 (8)	0.0032 (8)
C25	0.0208 (11)	0.0289 (11)	0.0215 (11)	0.0077 (9)	0.0019 (8)	0.0053 (9)
C25A	0.0207 (10)	0.0278 (11)	0.0204 (11)	0.0097 (9)	0.0023 (8)	0.0052 (9)
C26	0.0246 (11)	0.0347 (12)	0.0206 (11)	0.0122 (9)	−0.0002 (9)	0.0075 (9)
C27	0.0322 (12)	0.0369 (13)	0.0213 (11)	0.0165 (10)	0.0020 (9)	0.0114 (10)
C28	0.0282 (12)	0.0285 (11)	0.0274 (12)	0.0097 (9)	0.0059 (9)	0.0121 (10)
C29	0.0232 (11)	0.0290 (11)	0.0225 (11)	0.0081 (9)	0.0007 (8)	0.0071 (9)
C29A	0.0208 (10)	0.0255 (11)	0.0195 (10)	0.0093 (8)	0.0016 (8)	0.0054 (9)
C29B	0.0192 (10)	0.0224 (10)	0.0181 (10)	0.0084 (8)	0.0022 (8)	0.0054 (8)
N210	0.0194 (9)	0.0221 (9)	0.0181 (9)	0.0047 (7)	0.0001 (7)	0.0055 (7)
C210	0.0185 (10)	0.0217 (10)	0.0188 (10)	0.0055 (8)	−0.0003 (8)	0.0040 (8)
C211	0.0183 (10)	0.0190 (10)	0.0220 (11)	0.0036 (8)	0.0001 (8)	0.0039 (8)
C212	0.0217 (11)	0.0261 (11)	0.0197 (11)	0.0034 (9)	0.0002 (8)	0.0038 (9)
C213	0.0242 (11)	0.0262 (11)	0.0266 (12)	0.0047 (9)	0.0055 (9)	0.0062 (9)
C214	0.0181 (10)	0.0190 (10)	0.0313 (12)	0.0025 (8)	−0.0015 (9)	−0.0009 (9)
Cl24	0.0207 (3)	0.0382 (3)	0.0403 (3)	−0.0038 (2)	−0.0004 (2)	−0.0031 (3)
C215	0.0228 (11)	0.0252 (11)	0.0227 (11)	0.0050 (9)	−0.0036 (8)	0.0026 (9)
C216	0.0235 (11)	0.0243 (11)	0.0196 (11)	0.0044 (9)	0.0021 (8)	0.0055 (9)
C231	0.0192 (10)	0.0254 (11)	0.0174 (10)	0.0025 (8)	−0.0002 (8)	0.0064 (9)
C232	0.0254 (11)	0.0303 (11)	0.0188 (11)	0.0039 (9)	0.0010 (8)	0.0071 (9)
C233	0.0362 (13)	0.0218 (11)	0.0246 (12)	0.0011 (9)	−0.0012 (9)	0.0081 (9)
C234	0.0203 (11)	0.0493 (15)	0.0263 (12)	0.0055 (10)	0.0033 (9)	0.0133 (11)
C241	0.0184 (10)	0.0237 (10)	0.0154 (10)	0.0037 (8)	−0.0008 (8)	0.0051 (8)
C242	0.0218 (10)	0.0274 (11)	0.0245 (11)	0.0082 (9)	0.0036 (8)	0.0052 (9)
C243	0.0299 (12)	0.0202 (10)	0.0288 (12)	0.0061 (9)	0.0049 (9)	0.0030 (9)
C244	0.0235 (11)	0.0211 (10)	0.0190 (11)	−0.0014 (8)	0.0014 (8)	0.0039 (8)
C245	0.0181 (10)	0.0271 (11)	0.0260 (11)	0.0045 (9)	0.0002 (8)	0.0052 (9)
C246	0.0212 (10)	0.0225 (10)	0.0255 (11)	0.0061 (8)	−0.0005 (8)	0.0028 (9)
O244	0.0246 (8)	0.0243 (8)	0.0379 (9)	−0.0018 (6)	0.0048 (7)	0.0022 (7)
C247	0.0215 (11)	0.0364 (13)	0.0374 (14)	−0.0035 (10)	−0.0005 (10)	0.0045 (11)
O25	0.0230 (8)	0.0412 (9)	0.0239 (8)	−0.0017 (7)	−0.0051 (6)	0.0083 (7)

Geometric parameters (Å, º)

N11—C110	1.361 (3)	N21—C210	1.364 (2)
N11—N12	1.377 (2)	N21—N22	1.373 (2)
N11—C111	1.424 (2)	N21—C211	1.422 (2)
N12—C13	1.320 (3)	N22—C23	1.323 (2)
C13—C13A	1.453 (3)	C23—C23A	1.456 (3)
C13—C131	1.525 (3)	C23—C231	1.521 (3)
C13A—C110	1.420 (3)	C23A—C210	1.423 (3)
C13A—C14	1.424 (3)	C23A—C24	1.424 (3)
C14—C14A	1.394 (3)	C24—C24A	1.384 (3)
C14—C141	1.497 (3)	C24—C241	1.497 (3)
C14A—C19B	1.420 (3)	C24A—C29B	1.417 (3)
C14A—C15	1.492 (3)	C24A—C25	1.502 (3)
C15—O15	1.218 (2)	C25—O25	1.217 (2)
C15—C15A	1.501 (3)	C25—C25A	1.498 (3)
C15A—C16	1.382 (3)	C25A—C26	1.388 (3)
C15A—C19A	1.393 (3)	C25A—C29A	1.396 (3)
C16—C17	1.390 (3)	C26—C27	1.391 (3)
C16—H16	0.9500	C26—H26	0.9500
C17—C18	1.385 (3)	C27—C28	1.393 (3)
C17—H17	0.9500	C27—H27	0.9500
C18—C19	1.393 (3)	C28—C29	1.394 (3)
C18—H18	0.9500	C28—H28	0.9500
C19—C19A	1.390 (3)	C29—C29A	1.378 (3)
C19—H19	0.9500	C29—H29	0.9500
C19A—C19B	1.478 (3)	C29A—C29B	1.477 (3)
C19B—N110	1.319 (3)	C29B—N210	1.323 (2)
N110—C110	1.354 (2)	N210—C210	1.348 (2)
C111—C116	1.386 (3)	C211—C212	1.391 (3)
C111—C112	1.390 (3)	C211—C216	1.396 (3)
C112—C113	1.385 (3)	C212—C213	1.388 (3)
C112—H112	0.9500	C212—H212	0.9500
C113—C114	1.377 (3)	C213—C214	1.381 (3)
C113—H113	0.9500	C213—H213	0.9500
C114—C115	1.379 (3)	C214—C215	1.378 (3)
C114—Cl14	1.743 (2)	C214—Cl24	1.742 (2)
C115—C116	1.386 (3)	C215—C216	1.391 (3)
C115—H115	0.9500	C215—H215	0.9500
C116—H116	0.9500	C216—H216	0.9500
C131—C133	1.528 (3)	C231—C233	1.534 (3)
C131—C132	1.531 (3)	C231—C234	1.536 (3)
C131—C134	1.535 (3)	C231—C232	1.536 (3)
C132—H13A	0.9800	C232—H23A	0.9800
C132—H13B	0.9800	C232—H23B	0.9800
C132—H13C	0.9800	C232—H23C	0.9800
C133—H13D	0.9800	C233—H23D	0.9800
C133—H13E	0.9800	C233—H23E	0.9800
C133—H13F	0.9800	C233—H23F	0.9800
C134—H13G	0.9800	C234—H23G	0.9800
C134—H13H	0.9800	C234—H23H	0.9800
C134—H13I	0.9800	C234—H23I	0.9800
C141—C142	1.389 (3)	C241—C246	1.386 (3)
C141—C146	1.396 (3)	C241—C242	1.390 (3)
C142—C143	1.389 (3)	C242—C243	1.383 (3)
C142—H142	0.9500	C242—H242	0.9500
C143—C144	1.385 (3)	C243—C244	1.388 (3)
C143—H143	0.9500	C243—H243	0.9500
C144—O144	1.374 (2)	C244—O244	1.374 (2)
C144—C145	1.390 (3)	C244—C245	1.381 (3)
C145—C146	1.384 (3)	C245—C246	1.391 (3)
C145—H145	0.9500	C245—H245	0.9500
C146—H146	0.9500	C246—H246	0.9500
O144—C147	1.426 (3)	O244—C247	1.424 (3)
C147—H14A	0.9800	C247—H24A	0.9800
C147—H14B	0.9800	C247—H24B	0.9800
C147—H14C	0.9800	C247—H24C	0.9800
C110—N11—N12	110.55 (16)	C210—N21—N22	110.44 (15)
C110—N11—C111	130.81 (17)	C210—N21—C211	130.66 (17)
N12—N11—C111	118.50 (16)	N22—N21—C211	118.70 (15)
C13—N12—N11	107.99 (16)	C23—N22—N21	108.42 (15)
N12—C13—C13A	110.04 (17)	N22—C23—C23A	109.68 (16)
N12—C13—C131	116.89 (17)	N22—C23—C231	117.16 (17)
C13A—C13—C131	133.04 (18)	C23A—C23—C231	133.15 (17)
C110—C13A—C14	117.14 (18)	C210—C23A—C24	117.15 (17)
C110—C13A—C13	103.88 (17)	C210—C23A—C23	103.91 (16)
C14—C13A—C13	138.97 (18)	C24—C23A—C23	138.94 (18)
C14A—C14—C13A	114.81 (18)	C24A—C24—C23A	114.57 (17)
C14A—C14—C141	117.70 (18)	C24A—C24—C241	118.63 (17)
C13A—C14—C141	127.46 (18)	C23A—C24—C241	126.80 (17)
C14—C14A—C19B	121.66 (18)	C24—C24A—C29B	122.18 (18)
C14—C14A—C15	130.32 (18)	C24—C24A—C25	130.48 (18)
C19B—C14A—C15	107.89 (17)	C29B—C24A—C25	107.34 (17)
O15—C15—C14A	128.89 (19)	O25—C25—C25A	125.94 (19)
O15—C15—C15A	125.61 (19)	O25—C25—C24A	128.48 (19)
C14A—C15—C15A	105.49 (16)	C25A—C25—C24A	105.58 (17)
C16—C15A—C19A	121.49 (19)	C26—C25A—C29A	121.10 (19)
C16—C15A—C15	129.36 (19)	C26—C25A—C25	129.67 (19)
C19A—C15A—C15	109.09 (17)	C29A—C25A—C25	109.22 (17)
C15A—C16—C17	117.9 (2)	C25A—C26—C27	118.1 (2)
C15A—C16—H16	121.1	C25A—C26—H26	121.0
C17—C16—H16	121.1	C27—C26—H26	121.0
C18—C17—C16	120.8 (2)	C26—C27—C28	120.79 (19)
C18—C17—H17	119.6	C26—C27—H27	119.6
C16—C17—H17	119.6	C28—C27—H27	119.6
C17—C18—C19	121.5 (2)	C27—C28—C29	120.7 (2)
C17—C18—H18	119.2	C27—C28—H28	119.6
C19—C18—H18	119.2	C29—C28—H28	119.6
C19A—C19—C18	117.48 (19)	C29A—C29—C28	118.5 (2)
C19A—C19—H19	121.3	C29A—C29—H29	120.7
C18—C19—H19	121.3	C28—C29—H29	120.7
C19—C19A—C15A	120.79 (18)	C29—C29A—C25A	120.78 (18)
C19—C19A—C19B	130.56 (18)	C29—C29A—C29B	130.93 (19)
C15A—C19A—C19B	108.58 (17)	C25A—C29A—C29B	108.29 (17)
N110—C19B—C14A	125.64 (18)	N210—C29B—C24A	125.44 (18)
N110—C19B—C19A	125.34 (18)	N210—C29B—C29A	125.00 (18)
C14A—C19B—C19A	108.93 (17)	C24A—C29B—C29A	109.56 (17)
C19B—N110—C110	112.05 (17)	C29B—N210—C210	111.92 (16)
N110—C110—N11	123.82 (17)	N210—C210—N21	123.80 (17)
N110—C110—C13A	128.65 (18)	N210—C210—C23A	128.63 (18)
N11—C110—C13A	107.53 (17)	N21—C210—C23A	107.52 (16)
C116—C111—C112	120.08 (19)	C212—C211—C216	119.84 (18)
C116—C111—N11	118.33 (18)	C212—C211—N21	121.24 (18)
C112—C111—N11	121.58 (18)	C216—C211—N21	118.81 (17)
C113—C112—C111	119.77 (19)	C213—C212—C211	120.10 (19)
C113—C112—H112	120.1	C213—C212—H212	119.9
C111—C112—H112	120.1	C211—C212—H212	119.9
C114—C113—C112	119.7 (2)	C214—C213—C212	119.54 (19)
C114—C113—H113	120.1	C214—C213—H213	120.2
C112—C113—H113	120.1	C212—C213—H213	120.2
C113—C114—C115	120.96 (19)	C215—C214—C213	121.07 (19)
C113—C114—Cl14	118.84 (16)	C215—C214—Cl24	119.60 (16)
C115—C114—Cl14	120.20 (16)	C213—C214—Cl24	119.31 (16)
C114—C115—C116	119.60 (19)	C214—C215—C216	119.80 (19)
C114—C115—H115	120.2	C214—C215—H215	120.1
C116—C115—H115	120.2	C216—C215—H215	120.1
C115—C116—C111	119.86 (19)	C215—C216—C211	119.62 (19)
C115—C116—H116	120.1	C215—C216—H216	120.2
C111—C116—H116	120.1	C211—C216—H216	120.2
C13—C131—C133	109.44 (16)	C23—C231—C233	110.22 (16)
C13—C131—C132	109.87 (17)	C23—C231—C234	111.08 (16)
C133—C131—C132	108.44 (18)	C233—C231—C234	110.89 (18)
C13—C131—C134	110.52 (17)	C23—C231—C232	108.83 (16)
C133—C131—C134	110.39 (18)	C233—C231—C232	107.78 (17)
C132—C131—C134	108.15 (17)	C234—C231—C232	107.94 (17)
C131—C132—H13A	109.5	C231—C232—H23A	109.5
C131—C132—H13B	109.5	C231—C232—H23B	109.5
H13A—C132—H13B	109.5	H23A—C232—H23B	109.5
C131—C132—H13C	109.5	C231—C232—H23C	109.5
H13A—C132—H13C	109.5	H23A—C232—H23C	109.5
H13B—C132—H13C	109.5	H23B—C232—H23C	109.5
C131—C133—H13D	109.5	C231—C233—H23D	109.5
C131—C133—H13E	109.5	C231—C233—H23E	109.5
H13D—C133—H13E	109.5	H23D—C233—H23E	109.5
C131—C133—H13F	109.5	C231—C233—H23F	109.5
H13D—C133—H13F	109.5	H23D—C233—H23F	109.5
H13E—C133—H13F	109.5	H23E—C233—H23F	109.5
C131—C134—H13G	109.5	C231—C234—H23G	109.5
C131—C134—H13H	109.5	C231—C234—H23H	109.5
H13G—C134—H13H	109.5	H23G—C234—H23H	109.5
C131—C134—H13I	109.5	C231—C234—H23I	109.5
H13G—C134—H13I	109.5	H23G—C234—H23I	109.5
H13H—C134—H13I	109.5	H23H—C234—H23I	109.5
C142—C141—C146	118.80 (18)	C246—C241—C242	118.14 (18)
C142—C141—C14	120.42 (18)	C246—C241—C24	120.51 (18)
C146—C141—C14	120.35 (18)	C242—C241—C24	121.13 (17)
C141—C142—C143	120.88 (19)	C243—C242—C241	120.95 (19)
C141—C142—H142	119.6	C243—C242—H242	119.5
C143—C142—H142	119.6	C241—C242—H242	119.5
C144—C143—C142	119.76 (19)	C242—C243—C244	119.92 (19)
C144—C143—H143	120.1	C242—C243—H243	120.0
C142—C143—H143	120.1	C244—C243—H243	120.0
O144—C144—C143	124.49 (19)	O244—C244—C245	123.93 (18)
O144—C144—C145	115.60 (18)	O244—C244—C243	115.86 (18)
C143—C144—C145	119.91 (18)	C245—C244—C243	120.21 (18)
C146—C145—C144	120.06 (19)	C244—C245—C246	119.07 (19)
C146—C145—H145	120.0	C244—C245—H245	120.5
C144—C145—H145	120.0	C246—C245—H245	120.5
C145—C146—C141	120.53 (19)	C241—C246—C245	121.71 (19)
C145—C146—H146	119.7	C241—C246—H246	119.1
C141—C146—H146	119.7	C245—C246—H246	119.1
C144—O144—C147	116.50 (16)	C244—O244—C247	117.41 (17)
O144—C147—H14A	109.5	O244—C247—H24A	109.5
O144—C147—H14B	109.5	O244—C247—H24B	109.5
H14A—C147—H14B	109.5	H24A—C247—H24B	109.5
O144—C147—H14C	109.5	O244—C247—H24C	109.5
H14A—C147—H14C	109.5	H24A—C247—H24C	109.5
H14B—C147—H14C	109.5	H24B—C247—H24C	109.5
C110—N11—N12—C13	−1.0 (2)	C210—N21—N22—C23	−0.6 (2)
C111—N11—N12—C13	175.01 (17)	C211—N21—N22—C23	174.83 (17)
N11—N12—C13—C13A	0.1 (2)	N21—N22—C23—C23A	−0.5 (2)
N11—N12—C13—C131	−178.16 (16)	N21—N22—C23—C231	178.74 (16)
N12—C13—C13A—C110	0.7 (2)	N22—C23—C23A—C210	1.3 (2)
C131—C13—C13A—C110	178.7 (2)	C231—C23—C23A—C210	−177.8 (2)
N12—C13—C13A—C14	−177.7 (2)	N22—C23—C23A—C24	−179.2 (2)
C131—C13—C13A—C14	0.2 (4)	C231—C23—C23A—C24	1.7 (4)
C110—C13A—C14—C14A	2.4 (3)	C210—C23A—C24—C24A	3.3 (3)
C13—C13A—C14—C14A	−179.3 (2)	C23—C23A—C24—C24A	−176.2 (2)
C110—C13A—C14—C141	−175.69 (19)	C210—C23A—C24—C241	−176.39 (18)
C13—C13A—C14—C141	2.6 (4)	C23—C23A—C24—C241	4.2 (4)
C13A—C14—C14A—C19B	−1.3 (3)	C23A—C24—C24A—C29B	−1.1 (3)
C141—C14—C14A—C19B	177.01 (18)	C241—C24—C24A—C29B	178.58 (18)
C13A—C14—C14A—C15	−176.64 (19)	C23A—C24—C24A—C25	179.28 (19)
C141—C14—C14A—C15	1.7 (3)	C241—C24—C24A—C25	−1.0 (3)
C14—C14A—C15—O15	−3.4 (4)	C24—C24A—C25—O25	0.4 (4)
C19B—C14A—C15—O15	−179.2 (2)	C29B—C24A—C25—O25	−179.2 (2)
C14—C14A—C15—C15A	175.8 (2)	C24—C24A—C25—C25A	−179.6 (2)
C19B—C14A—C15—C15A	0.0 (2)	C29B—C24A—C25—C25A	0.8 (2)
O15—C15—C15A—C16	2.6 (3)	O25—C25—C25A—C26	−0.8 (4)
C14A—C15—C15A—C16	−176.7 (2)	C24A—C25—C25A—C26	179.2 (2)
O15—C15—C15A—C19A	179.96 (19)	O25—C25—C25A—C29A	179.8 (2)
C14A—C15—C15A—C19A	0.7 (2)	C24A—C25—C25A—C29A	−0.2 (2)
C19A—C15A—C16—C17	−0.1 (3)	C29A—C25A—C26—C27	0.4 (3)
C15—C15A—C16—C17	177.0 (2)	C25—C25A—C26—C27	−179.0 (2)
C15A—C16—C17—C18	0.7 (3)	C25A—C26—C27—C28	0.5 (3)
C16—C17—C18—C19	−0.4 (3)	C26—C27—C28—C29	−1.1 (3)
C17—C18—C19—C19A	−0.5 (3)	C27—C28—C29—C29A	0.8 (3)
C18—C19—C19A—C15A	1.0 (3)	C28—C29—C29A—C25A	0.1 (3)
C18—C19—C19A—C19B	−175.6 (2)	C28—C29—C29A—C29B	179.1 (2)
C16—C15A—C19A—C19	−0.8 (3)	C26—C25A—C29A—C29	−0.7 (3)
C15—C15A—C19A—C19	−178.43 (18)	C25—C25A—C29A—C29	178.79 (18)
C16—C15A—C19A—C19B	176.52 (18)	C26—C25A—C29A—C29B	−179.91 (18)
C15—C15A—C19A—C19B	−1.1 (2)	C25—C25A—C29A—C29B	−0.4 (2)
C14—C14A—C19B—N110	−0.2 (3)	C24—C24A—C29B—N210	−1.3 (3)
C15—C14A—C19B—N110	176.03 (18)	C25—C24A—C29B—N210	178.38 (18)
C14—C14A—C19B—C19A	−176.89 (18)	C24—C24A—C29B—C29A	179.27 (18)
C15—C14A—C19B—C19A	−0.6 (2)	C25—C24A—C29B—C29A	−1.0 (2)
C19—C19A—C19B—N110	1.4 (3)	C29—C29A—C29B—N210	2.4 (3)
C15A—C19A—C19B—N110	−175.57 (19)	C25A—C29A—C29B—N210	−178.51 (19)
C19—C19A—C19B—C14A	178.1 (2)	C29—C29A—C29B—C24A	−178.2 (2)
C15A—C19A—C19B—C14A	1.1 (2)	C25A—C29A—C29B—C24A	0.9 (2)
C14A—C19B—N110—C110	0.5 (3)	C24A—C29B—N210—C210	1.1 (3)
C19A—C19B—N110—C110	176.61 (18)	C29A—C29B—N210—C210	−179.52 (18)
C19B—N110—C110—N11	−179.07 (18)	C29B—N210—C210—N21	178.46 (18)
C19B—N110—C110—C13A	1.0 (3)	C29B—N210—C210—C23A	1.5 (3)
N12—N11—C110—N110	−178.47 (18)	N22—N21—C210—N210	−176.10 (17)
C111—N11—C110—N110	6.1 (3)	C211—N21—C210—N210	9.2 (3)
N12—N11—C110—C13A	1.5 (2)	N22—N21—C210—C23A	1.4 (2)
C111—N11—C110—C13A	−173.90 (19)	C211—N21—C210—C23A	−173.28 (19)
C14—C13A—C110—N110	−2.5 (3)	C24—C23A—C210—N210	−3.9 (3)
C13—C13A—C110—N110	178.6 (2)	C23—C23A—C210—N210	175.75 (19)
C14—C13A—C110—N11	177.51 (17)	C24—C23A—C210—N21	178.80 (17)
C13—C13A—C110—N11	−1.3 (2)	C23—C23A—C210—N21	−1.6 (2)
C110—N11—C111—C116	−161.9 (2)	C210—N21—C211—C212	18.5 (3)
N12—N11—C111—C116	23.0 (3)	N22—N21—C211—C212	−155.80 (18)
C110—N11—C111—C112	18.5 (3)	C210—N21—C211—C216	−165.4 (2)
N12—N11—C111—C112	−156.56 (19)	N22—N21—C211—C216	20.3 (3)
C116—C111—C112—C113	0.5 (3)	C216—C211—C212—C213	−1.0 (3)
N11—C111—C112—C113	−179.94 (19)	N21—C211—C212—C213	175.11 (18)
C111—C112—C113—C114	−0.6 (3)	C211—C212—C213—C214	0.1 (3)
C112—C113—C114—C115	0.2 (3)	C212—C213—C214—C215	0.5 (3)
C112—C113—C114—Cl14	−179.43 (17)	C212—C213—C214—Cl24	179.22 (16)
C113—C114—C115—C116	0.3 (3)	C213—C214—C215—C216	−0.2 (3)
Cl14—C114—C115—C116	179.91 (16)	Cl24—C214—C215—C216	−178.94 (16)
C114—C115—C116—C111	−0.4 (3)	C214—C215—C216—C211	−0.7 (3)
C112—C111—C116—C115	0.0 (3)	C212—C211—C216—C215	1.3 (3)
N11—C111—C116—C115	−179.59 (19)	N21—C211—C216—C215	−174.93 (18)
N12—C13—C131—C133	108.3 (2)	N22—C23—C231—C233	105.2 (2)
C13A—C13—C131—C133	−69.6 (3)	C23A—C23—C231—C233	−75.8 (3)
N12—C13—C131—C132	−10.7 (2)	N22—C23—C231—C234	−131.46 (19)
C13A—C13—C131—C132	171.5 (2)	C23A—C23—C231—C234	47.5 (3)
N12—C13—C131—C134	−129.98 (19)	N22—C23—C231—C232	−12.8 (2)
C13A—C13—C131—C134	52.2 (3)	C23A—C23—C231—C232	166.2 (2)
C14A—C14—C141—C142	−93.5 (2)	C24A—C24—C241—C246	71.6 (3)
C13A—C14—C141—C142	84.6 (3)	C23A—C24—C241—C246	−108.7 (2)
C14A—C14—C141—C146	78.8 (2)	C24A—C24—C241—C242	−102.8 (2)
C13A—C14—C141—C146	−103.1 (2)	C23A—C24—C241—C242	76.8 (3)
C146—C141—C142—C143	−0.8 (3)	C246—C241—C242—C243	1.1 (3)
C14—C141—C142—C143	171.57 (19)	C24—C241—C242—C243	175.63 (19)
C141—C142—C143—C144	0.0 (3)	C241—C242—C243—C244	−0.2 (3)
C142—C143—C144—O144	−177.4 (2)	C242—C243—C244—O244	179.91 (19)
C142—C143—C144—C145	1.8 (3)	C242—C243—C244—C245	−0.4 (3)
O144—C144—C145—C146	176.40 (18)	O244—C244—C245—C246	179.73 (19)
C143—C144—C145—C146	−2.8 (3)	C243—C244—C245—C246	0.1 (3)
C144—C145—C146—C141	2.0 (3)	C242—C241—C246—C245	−1.4 (3)
C142—C141—C146—C145	−0.2 (3)	C24—C241—C246—C245	−176.03 (19)
C14—C141—C146—C145	−172.61 (19)	C244—C245—C246—C241	0.9 (3)
C143—C144—O144—C147	10.7 (3)	C245—C244—O244—C247	3.2 (3)
C145—C144—O144—C147	−168.46 (19)	C243—C244—O244—C247	−177.08 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O25^i	0.95	2.50	3.151 (3)	126
C28—H28···O15^ii	0.95	2.46	3.226 (3)	138
C146—H146···Cg	0.95	2.71	3.655 (2)	172

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