Two closely related, and unexpected, quinolinone derivatives: a three-dimensional hydrogen-bonded framework structure and a hydrogen-bonded mol­ecular ribbon of R₂²(18) and R₄⁴(24) rings

1,5-Bis(4-chloro­phenyl)-3-(2-oxo-1,2-dihydro­quinolin-3-yl)pentane-1,5-dione, (Ia), and 1,5-bis­(2-chloro­phenyl)-3-(2-oxo-1,2-dihydro­quinolin-3-yl)pentane-1,5-dione, (Ib), crystallize as an 84:16 mixture, 0.84C₂₆H₁₉Cl₂NO₃·0.16C₂₆H₁₉Cl₂NO₃, in the space group I4₁/a, where the mol­ecules of the two isomers occupy very similar sites in the unit cell. A combination of one N—H...O hydrogen bond and one C—H...O hydrogen bond links the mol­ecules, regardless of isomeric form, into a single three-dimensional framework structure. The mol­ecules of (9RS,10RS)-8,9-bis­(4-chloro­benzyl)-10-(2-oxo-1,2-dihydroquinolin-3-yl)-5,6,9,10-tetra­hydro­phenanthridine, C₃₆H₂₂Cl₂N₂O₄, (II), are linked by two hydrogen bonds, one each of the N—H...O and C—H...O types, into a mol­ecular ribbon in which centrosymmetric rings of R₂²(18) and R₄⁴(24) types alternate. The hydrogen-bonded ribbons enclose channels, which contain highly disordered solvent mol­ecules.

S1. Comment

We report here the molecular and supramolecular structures of two closely related compounds, namely 1,5-bis(4-chlorophenyl)-3-(2-oxo-1,2-dihydroquinolin-3-yl)pentane-1,5-dione–1,5-bis(2-chlorophenyl)-3-(2-oxo-1,2-dihydroquinolin-3-yl)pentane-1,5-dione (84/16), (I) (Fig. 1), and (9RS,10RS)-8,9-bis(4-chlorobenzyl)-10-(2-oxo-1,2-dihydroquinolin-3-yl)-5,6,9,10-tetrahydrophenanthridine, (II) (Fig. 2), both of which were initially identified as unexpected by-products in the synthesis of a simple chalcone. As part of a synthetic programme focusing on novel quinolin-2-one derivatives having potential as antitumour agents (Abonía et al., 2010), we have prepared a number of chalcones containing both quinolin-2-one and benzoyl units. In the preparation of the chalcone, (A) (see Scheme 1), by base-catalysed condensation between 2-oxoquinoline-3-carbaldehyde and 4-chloroacetophenone, compound (I) was also isolated, but in trace amounts, presumably resulting from a Michael-type addition reaction between chalcone (A) and further 4-chloroacetophenone. Subsequently, the reaction between chalcone (A) and an excess of 4-chloroacetophenone under basic conditions was, indeed, found to provide an acceptable yield of (I), which was found from the structural study to be, in fact, an 84:16 mixture of the two isomeric compounds (Ia) and (Ib) (see below). The origin of the 2-chloro substituent was eventually traced to one batch of commercial 4-chloroacetophenone, as used in the conversion of (A) to (I). Consistent with this, there is no evidence for the presence of any 2-chloro substituent either in the other chlorinated aryl ring in (I) or in (II). As discussed below, the occurrence of the 2-chloro isomer, (Ib), has a negligible effect on the supramolecular aggregation in (I). When chalcone (A) was crystallized from hot dimethylformamide solution, trace quantities of a second compound, (II), were also obtained, apparently resulting from a Diels–Alder type dimerization of (A), accompanied by the loss of two H atoms by aerial oxidation (see Scheme 2).

Compound (I) contains geometric isomers (Ia) and (Ib) (Fig. 1) in an 84:16 ratio in the crystal selected for data collection. It is possible that this ratio may vary somewhat from one crystal to another and, in view of this and the absence of a simple small-integer ratio between the abundances of the two components, it may be better to regard (I) as a solid solution rather than as a cocrystal (Aitipamula et al., 2012). Compound (I) crystallizes in the rather uncommon space group I4₁/a; in the February 2012 release of the Cambridge Structural Database (Allen, 2002), only 2086 entries out of a total of 603298, ca 0.35%, have space group I4₁/a. In (I), the two isomeric forms occupy very similar positions within the unit cell (Fig. 3) and the similarity of the molecular conformations is confirmed by a comparison of the torsion angles (Table 1). Although the experimental uncertainties on the values for the minor isomer are fairly substantial, within that constraint the corresponding values for the two isomers are, in general, closely similar. In addition, the very different values (Table 1) of the two torsion angles Cx1—Cx2—Cx3—Cx4 and Cx2—Cx3—Cx4—Cx5 (where x = 1 or 2), which define the conformation of the molecular backbone in each isomer, show that the molecules of isomers (Ia) and (Ib) can have no internal symmetry. Both isomers are thus conformationally chiral, although the centrosymmetric space group accommodates equal numbers of the two conformational enantiomers. The close similarity between the conformations of (Ia) and (Ib) may be a straightforward consequence of the nature of the structure in which, at a minority of the molecular sites, a molecule of (Ib) has simply replaced a molecule of (Ia) and is thus constrained to adopt essentially the same overall molecular shape.

In the molecule of (II) (Fig. 2), there are two stereogenic centres, at atoms C9 and C10, and the compound crystallizes as a true racemate with configuration (9RS,10RS). For the (9R,10R) enantiomer, ring C6a/C7/C8/C9/C10/C10a adopts a screw-boat conformation, with atoms C9 and C10 displaced on opposite sides of the mean plane of the ring by 0.220 (2) and 0.213 (2) Å, respectively. The ring-puckering parameters (Cremer & Pople, 1975) are Q = 0.342 (2) Å, θ = 61.9 (3)° and ϕ = 207.5 (4)°; for an idealized screw-boat form the ring-puckering angles are θ = 67.5° and ϕ =(60k + 30)°, where k represents an integer. The substituent atoms C97 and C103 (Fig. 2) both adopt axial positions on the screw-boat ring, presumably in order to minimize the steric interactions between the acyl substituent at C9 and the quinolinone substituent at C10.

In the crystal structure of (I), the hydrogen bonds involving the two isomeric forms (Ia) and (Ib) are essentially the same (Table 2), as might be expected from the similarity of the two molecular conformations. Accordingly, it is necessary only to discuss the supramolecular aggregation of (Ia). Two hydrogen bonds, one each of N—H···O and C—H···O types, link the molecules of (Ia) into a single three-dimensional framework, and it is convenient to analyse the formation of the framework in terms of two simple substructures (Ferguson et al., 1998a,b; Gregson et al., 2000), each involving just one type of hydrogen bond, and which are respectively one- and zero-dimensional.

The one-dimensional substructure of (I) takes the form of a simple chain built using a C—H···O hydrogen bond having an aryl C—H unit as the donor. Aryl atom C156 in the molecule of (Ia) at (x, y, z) acts as hydrogen-bond donor to acyl atom O15 in the molecule at (y + 1/4, -x + 5/4, z + 1/4), while atom C156 at (y + 1/4, -x + 5/4, z + 1/4) in turn acts as donor to atom O15 at (-x + 3/2, -y + 1, z + 1/2), and so on, thereby forming a C(5) (Bernstein et al., 1995) helical chain running parallel to the [001] direction and containing molecules related by the 4₃ screw axis along (3/4, 1/2, z) (Fig. 4). There is also present a rather long C—H···O contact involving an aliphatic C—H unit; even if this were regarded as structurally significant, its role would be simply to reinforce the chain motif discussed above.

In the second, zero-dimensional, substructure, paired N—H···O hydrogen bonds link the molecules at (x, y, z) and (-x + 1, -y + 1, -z + 1) into a centrosymmetric dimer characterized by an R₂²(8) motif (Fig. 5). The molecule at (-x + 1, -y + 1, -z + 1) is a component of the C(5) chain built from molecules related by the 4₁ screw axis along (1/4, 1/2, z). Hence, the combination of these two motifs directly links the C(5) chain along (3/4, 1/2, z) to the four analogous chains along (1/4, 1/2, z), (1.25, 1/2, z), (3/4, 0, z) and (3/4, 1, z), thus, in turn, linking all of the C(5) chains into a continuous framework structure. Replacement, at any randomly selected molecular site, of a molecule of (Ia) by a molecule of (Ib) will have no significant influence on the supramolecular aggregation, as the direction-specific intermolecular interactions involving (Ia) and (Ib) are entirely equivalent (Table 2).

The supramolecular aggregation in (II) also involves a combination of N—H···O and C—H···O hydrogen bonds (Table 2), but here the resulting hydrogen-bonded structure is only one-dimensional. Acting in isolation, the N—H···O hydrogen bond links molecules of (II) related by translation into a C(9) chain running parallel to the [100] direction, while the C—H···O hydrogen bond, acting alone, links inversion-related pairs of molecules to form an R₂²(18) motif. In combination, the two hydrogen bonds generate a molecular ribbon parallel to [100], in which centrosymmetric rings centred at (n, 1/2, 0) alternate with centrosymmetric R₄⁴(24) rings centred at (n + 1/2, 1/2, 0), where n represents an integer in each case (Fig. 6). The only other direction-specific intermolecular contact in the structure of (II) (Table 2) has a fairly long H···O distance and, more significantly, a small C—H···O angle, and for this reason alone (cf. Wood et al., 2009) it is not regarded as structurally significant. Even if this contact were significant, it would not affect the overall supramolecular aggregation, since its action would simply be a reinforcement of the chain generated by the N—H···O hydrogen bond. The stacking of the hydrogen-bonded ribbons is such as to enclose substantial cavities. Although PLATON (Spek, 2009) indicates the presence of two such spaces, centred close to the origin and to (1/2, 0, 1/2), this space, in fact, takes the form of a single continuous channel parallel to [100] (Fig. 7). This space appears to contain disordered solvent molecules, but no chemically sensible model could be developed to account for the associated peaks in the difference map (see Refinement section). It is possible that the solvent species within the channels are mobile (Farrell et al., 2002).

Related literature

For related literature, see: Abonía et al. (2010); Aitipamula (2012); Allen (2002); Bernstein et al. (1995); Cremer & Pople (1975); Farrell et al. (2002); Ferguson et al. (1998a, 1998b); Gregson et al. (2000); Spek (2009); Wood et al. (2009).

S2. Experimental

For the synthesis of (I), a solution of chalcone (A) (100 mg, 0.32 mmol) and 4-chloroacetophenone (61 mg, 0.40 mmol, 1.25 equivalents) in a mixture of 95% aqueous ethanol (5 ml) and 20% aqueous sodium hydroxide solution (2 drops) was heated under reflux for 7 h; after this time, the chalcone had been completely consumed, as indicated by thin-layer chromatography. The mixture was cooled to ambient temperature and water (2 ml) was added. The resulting solid, (I), was collected by filtration and washed with water (2 × 0.5 ml). Colourless crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation, at ambient temperature and in air, of a solution in ethanol (yield 72%, m.p. 484 K). Analysis, found: C 67.0, H 4.3, N 2.9%; C₂₆H₁₉Cl₂NO₃ requires: C 67.3, H 4.1, N 3.0%.

Compound (II) was isolated in trace quantities as pale-yellow crystals, as a by-product during the crystallization of the colourless chalcone (A) from a solution in hot dimethylformamide (m.p. 519 K). Analysis, found: C 69.9, H 3.7, N 4.4%; C₃₆H₂₂Cl₂N₂O₄ requires: C 70.0, H 3.6, N 4.5%.

S3. Refinement

For (I), the space group I4₁/a was uniquely assigned from the systematic absences and the cell setting having the origin at a centre of inversion was employed. From an early stage in the refinement of (I) it was apparent that the Cl substituent on one of the aryl rings was distributed over two positions, corresponding to the presence of the two geometric isomers, (Ia) and (Ib) (Fig. 1), the molecules of which occupy very similar positions in the unit cell. This disorder was handled by restraining the bonded distances and the one-angle nonbonded distances in the minor isomer, (Ib), with the exception of those involving atom Cl22, to be equal to the corresponding distances in the major isomer, (Ia), subject to s.u. values of 0.005 and 0.01 Å, respectively. The C114—Cl14 and C212—Cl22 bond distances were restrained to the common value 1.74 (2) Å. In addition, the values of the anisotropic displacement parameter (ADP) components for the pairs of the corresponding atoms in the two isomers which occupy essentially the same physical space in different unit cells were constrained to be equal. Subject to these conditions, the refinement of (I) converged smoothly to give occupancy factors for the major and minor isomers of 0.840 (2) and 0.160 (2), respectively, in the crystal selected for data collection. Examination of the refined structure of (I) using PLATON (Spek, 2009) revealed the presence of a number of small voids at the special positions of 4 symmetry, each of volume ca 34 ų, too small to accommodate even the smallest of solvent molecules.

For (II) the reference molecule was selected as one having the R configuration at atoms C9 and C10. Conventional refinement converged at R = 0.162 for 7841 unique data, of which 5685 were labelled observed, from a total of 43906 measured reflections having R_int = 0.0413. Examination of this structure using PLATON (Spek, 2009) identified apparent void space around the origin (volume ca 274 ų) and around (1/2, 0, 1/2) (volume ca 126 ų). In addition, the difference map contained a number of substantial peaks, but it proved impossible to develop from these any sensible model for any plausible solvent species. It is possible both that more than one solvent species is present and that the solvent molecules are disordered over a number of sites, or even mobile. Accordingly, the data were subjected to the SQUEEZE procedure in PLATON, which indicated a total of ca 60 additional electrons per unit cell, and the refinement was then continued using the modified data set.

All H atoms in (Ia) and (II) were located in difference maps, while those in (Ib) were added in calculated positions. Subsequently, all H atoms were treated as riding in geometrically idealized positions, with C—H = 0.95 (aromatic), 0.99 (CH₂) or 1.00 Å (aliphatic CH), and N—H = 0.88 Å, and with U_iso(H) = 1.2U_eq(C,N).

Computing details

For both compounds, data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I); SIR2004 (Burla et al., 2005) for (II). For both compounds, 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 structures of (a) the major isomer, (Ia), and (b) the minor isomer, (Ib), of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The molecular structure of the (9R,10E) enantiomer of (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 3. The major component, (Ia) (solid lines), and the minor component, (Ib) (dashed lines), of (I), showing the similarity in orientation and conformation of the two components.
	Fig. 4. A stereoview of part of the crystal structure of (I), showing the formation of a hydrogen-bonded C(5) chain along (3/4, 1/2, z). For the sake of clarity, only the major isomer is included and H atoms not involved in the motif shown have been omitted.
	Fig. 5. Part of the crystal structure of (I), showing the formation of a centrosymmetric R2^2(8) dimer. For the sake of clarity, only the major isomer is included and H atoms not involved in the motif shown have been omitted. Atoms marked with an asterisk (*) are at the symmetry position (-x + 1, -y + 1, -z + 1).
	Fig. 6. A stereoview of part of the crystal structure of (II), showing the formation of a hydrogen-bonded ribbon along [100] consisting of alternating R2^2(18) and R4^4(24) rings. For the sake of clarity, H atoms not involved in the motif shown have been omitted.
	Fig. 7. A space-filling view, approximately along [100], of part of the crystal structure of (II), showing the channels between the hydrogen-bonded ribbons.

(I) 1,5-Bis(4-chlorophenyl)-3-(2-oxo-1,2-dihydroquinolin-3-yl)pentane-1,5-dione– 1,5-bis(2-chlorophenyl)-3-(2-oxo-1,2-dihydroquinolin-3-yl)pentane-1,5-dione (84/16)

Crystal data

0.84C26H19Cl2NO3·0.16C26H19Cl2NO3	Dx = 1.352 Mg m^−3
Mr = 464.32	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 5197 reflections
Hall symbol: -I 4ad	θ = 2.6–27.5°
a = 22.268 (4) Å	µ = 0.31 mm^−1
c = 18.398 (5) Å	T = 120 K
V = 9123 (4) Å^3	Block, colourless
Z = 16	0.34 × 0.34 × 0.26 mm
F(000) = 3840

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	5197 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	3789 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.6°
ϕ and ω scans	h = −23→26
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −28→28
Tmin = 0.902, Tmax = 0.923	l = −23→21
32275 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.159	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.075P)^2 + 12.591P] where P = (Fo^2 + 2Fc^2)/3
5197 reflections	(Δ/σ)max = 0.001
392 parameters	Δρmax = 0.45 e Å^−3
85 restraints	Δρmin = −0.33 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C11	0.7514 (2)	0.4056 (3)	0.61806 (19)	0.0300 (8)	0.840 (2)
O11	0.77632 (15)	0.4039 (2)	0.55915 (16)	0.0372 (9)	0.840 (2)
C12	0.69777 (16)	0.44558 (19)	0.6325 (2)	0.0297 (7)	0.840 (2)
H12A	0.7007	0.4609	0.6829	0.036*	0.840 (2)
H12B	0.6609	0.4209	0.6294	0.036*	0.840 (2)
C13	0.69102 (15)	0.49932 (14)	0.58104 (18)	0.0273 (6)	0.840 (2)
H13	0.6890	0.4843	0.5299	0.033*	0.840 (2)
C14	0.74499 (19)	0.5419 (2)	0.5882 (3)	0.0299 (7)	0.840 (2)
H14A	0.7465	0.5576	0.6385	0.036*	0.840 (2)
H14B	0.7824	0.5189	0.5796	0.036*	0.840 (2)
C15	0.7426 (4)	0.5942 (3)	0.5357 (3)	0.0296 (9)	0.840 (2)
O15	0.7085 (6)	0.5941 (3)	0.4840 (5)	0.0401 (7)	0.840 (2)
C111	0.77137 (14)	0.3661 (2)	0.67935 (19)	0.0323 (8)	0.840 (2)
C112	0.82614 (16)	0.3371 (3)	0.6750 (2)	0.0422 (11)	0.840 (2)
H112	0.8502	0.3417	0.6327	0.051*	0.840 (2)
C113	0.84636 (16)	0.3011 (2)	0.7318 (2)	0.0480 (11)	0.840 (2)
H113	0.8840	0.2812	0.7288	0.058*	0.840 (2)
C114	0.81046 (16)	0.2950 (2)	0.7926 (2)	0.0424 (9)	0.840 (2)
C115	0.75567 (19)	0.32306 (18)	0.7990 (2)	0.0416 (8)	0.840 (2)
H115	0.7320	0.3183	0.8416	0.050*	0.840 (2)
C116	0.73583 (16)	0.3584 (2)	0.7418 (2)	0.0359 (8)	0.840 (2)
H116	0.6978	0.3776	0.7449	0.043*	0.840 (2)
N131	0.5267 (2)	0.5420 (4)	0.5766 (4)	0.0290 (13)	0.840 (2)
H131	0.4943	0.5334	0.5513	0.035*	0.840 (2)
C132	0.5789 (2)	0.5143 (3)	0.5571 (3)	0.0272 (12)	0.840 (2)
O132	0.5797 (2)	0.4781 (2)	0.5050 (2)	0.0337 (10)	0.840 (2)
C133	0.63221 (14)	0.53015 (14)	0.59962 (16)	0.0246 (7)	0.840 (2)
C134	0.62657 (17)	0.5675 (3)	0.6574 (3)	0.0309 (14)	0.840 (2)
H134	0.6608	0.5750	0.6868	0.037*	0.840 (2)
C14A	0.57127 (15)	0.59616 (17)	0.67576 (18)	0.0282 (10)	0.840 (2)
C135	0.56578 (15)	0.63917 (13)	0.73190 (16)	0.0332 (8)	0.840 (2)
H135	0.5995	0.6488	0.7614	0.040*	0.840 (2)
C136	0.51164 (16)	0.66706 (14)	0.74379 (17)	0.0372 (8)	0.840 (2)
H136	0.5083	0.6967	0.7807	0.045*	0.840 (2)
C137	0.46149 (16)	0.65204 (15)	0.7019 (2)	0.0408 (11)	0.840 (2)
H137	0.4242	0.6713	0.7111	0.049*	0.840 (2)
C138	0.4654 (3)	0.6098 (5)	0.6476 (5)	0.0364 (17)	0.840 (2)
H138	0.4309	0.5992	0.6200	0.044*	0.840 (2)
C18A	0.52081 (16)	0.5826 (2)	0.6332 (2)	0.0275 (11)	0.840 (2)
C151	0.7830 (4)	0.6468 (3)	0.5492 (4)	0.0292 (13)	0.840 (2)
C152	0.7732 (4)	0.6995 (2)	0.5086 (3)	0.0339 (11)	0.840 (2)
H152	0.7410	0.7009	0.4748	0.041*	0.840 (2)
C153	0.8099 (4)	0.7492 (2)	0.5171 (3)	0.0371 (10)	0.840 (2)
H153	0.8033	0.7847	0.4897	0.045*	0.840 (2)
C154	0.8567 (2)	0.7455 (2)	0.5670 (4)	0.0354 (9)	0.840 (2)
Cl15	0.90456 (14)	0.80724 (13)	0.57680 (12)	0.0470 (4)	0.840 (2)
C155	0.86584 (15)	0.69545 (17)	0.6098 (2)	0.0384 (11)	0.840 (2)
H155	0.8973	0.6949	0.6446	0.046*	0.840 (2)
C156	0.82853 (15)	0.64589 (16)	0.6015 (2)	0.0335 (10)	0.840 (2)
H156	0.8339	0.6115	0.6313	0.040*	0.840 (2)
Cl14	0.83734 (5)	0.25127 (4)	0.86443 (5)	0.0547 (3)	0.840 (2)
C21	0.7602 (14)	0.4038 (14)	0.6271 (10)	0.0300 (8)	0.160 (2)
O21	0.7868 (10)	0.4085 (13)	0.5694 (10)	0.0372 (9)	0.160 (2)
C22	0.7056 (9)	0.4417 (9)	0.6445 (13)	0.0297 (7)	0.160 (2)
H22A	0.7104	0.4581	0.6942	0.036*	0.160 (2)
H22B	0.6699	0.4152	0.6449	0.036*	0.160 (2)
C23	0.6933 (7)	0.4940 (6)	0.5926 (10)	0.0273 (6)	0.160 (2)
H23	0.6913	0.4781	0.5418	0.033*	0.160 (2)
C24	0.7441 (9)	0.5406 (9)	0.5968 (18)	0.0299 (7)	0.160 (2)
H24A	0.7450	0.5579	0.6464	0.036*	0.160 (2)
H24B	0.7829	0.5202	0.5885	0.036*	0.160 (2)
C25	0.737 (3)	0.5912 (16)	0.542 (2)	0.0296 (9)	0.160 (2)
O25	0.707 (3)	0.585 (2)	0.488 (3)	0.0401 (7)	0.160 (2)
C211	0.7851 (9)	0.3666 (13)	0.6879 (12)	0.0323 (8)	0.160 (2)
C212	0.8406 (10)	0.3396 (17)	0.6811 (14)	0.0422 (11)	0.160 (2)
C213	0.8641 (9)	0.3038 (15)	0.7362 (14)	0.0480 (11)	0.160 (2)
H213	0.9036	0.2879	0.7329	0.058*	0.160 (2)
C214	0.8282 (10)	0.2920 (14)	0.7959 (12)	0.0424 (9)	0.160 (2)
H214	0.8443	0.2693	0.8350	0.051*	0.160 (2)
C215	0.7700 (10)	0.3122 (13)	0.8004 (12)	0.0416 (8)	0.160 (2)
H215	0.7438	0.2979	0.8373	0.050*	0.160 (2)
C216	0.7504 (9)	0.3540 (14)	0.7500 (13)	0.0359 (8)	0.160 (2)
H216	0.7133	0.3742	0.7573	0.043*	0.160 (2)
N231	0.5288 (11)	0.535 (3)	0.582 (3)	0.0290 (13)	0.160 (2)
H231	0.4979	0.5280	0.5531	0.035*	0.160 (2)
C232	0.5816 (9)	0.507 (2)	0.565 (2)	0.0272 (12)	0.160 (2)
O232	0.5839 (12)	0.4699 (15)	0.5140 (16)	0.0337 (10)	0.160 (2)
C233	0.6327 (7)	0.5207 (8)	0.6122 (10)	0.0246 (7)	0.160 (2)
C234	0.6258 (8)	0.561 (2)	0.666 (2)	0.0309 (14)	0.160 (2)
H234	0.6602	0.5737	0.6930	0.037*	0.160 (2)
C24A	0.5689 (7)	0.5864 (13)	0.6855 (13)	0.0282 (10)	0.160 (2)
C235	0.5594 (7)	0.6238 (8)	0.7465 (9)	0.0332 (8)	0.160 (2)
H235	0.5914	0.6313	0.7794	0.040*	0.160 (2)
C236	0.5041 (8)	0.6493 (8)	0.7584 (10)	0.0372 (8)	0.160 (2)
H236	0.4981	0.6750	0.7989	0.045*	0.160 (2)
C237	0.4566 (8)	0.6375 (12)	0.7109 (13)	0.0408 (11)	0.160 (2)
H237	0.4181	0.6543	0.7204	0.049*	0.160 (2)
C238	0.4647 (14)	0.602 (3)	0.651 (3)	0.0364 (17)	0.160 (2)
H238	0.4331	0.5968	0.6163	0.044*	0.160 (2)
C28A	0.5200 (8)	0.5733 (17)	0.6400 (16)	0.0275 (11)	0.160 (2)
C251	0.775 (2)	0.6463 (16)	0.553 (3)	0.0292 (13)	0.160 (2)
C252	0.773 (2)	0.6915 (14)	0.499 (2)	0.0339 (11)	0.160 (2)
H252	0.7471	0.6865	0.4584	0.041*	0.160 (2)
C253	0.8066 (19)	0.7432 (14)	0.506 (2)	0.0371 (10)	0.160 (2)
H253	0.8030	0.7749	0.4714	0.045*	0.160 (2)
C254	0.8464 (17)	0.7476 (13)	0.5639 (19)	0.0354 (9)	0.160 (2)
Cl25	0.8984 (8)	0.8065 (8)	0.5641 (9)	0.0470 (4)	0.160 (2)
C255	0.8522 (11)	0.7025 (10)	0.6150 (13)	0.0384 (11)	0.160 (2)
H255	0.8803	0.7063	0.6535	0.046*	0.160 (2)
C256	0.8165 (12)	0.6516 (9)	0.6096 (14)	0.0335 (10)	0.160 (2)
H256	0.8202	0.6203	0.6444	0.040*	0.160 (2)
Cl22	0.8947 (3)	0.3519 (3)	0.6176 (3)	0.0690 (19)	0.160 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.031 (2)	0.0329 (12)	0.0259 (15)	0.0002 (12)	−0.0011 (14)	−0.0022 (12)
O11	0.0361 (17)	0.0468 (14)	0.0286 (13)	0.0066 (13)	0.0035 (11)	−0.0023 (12)
C12	0.0338 (15)	0.0322 (13)	0.0231 (19)	0.0026 (10)	0.0013 (13)	0.0013 (11)
C13	0.0305 (12)	0.0298 (12)	0.0217 (15)	0.0013 (9)	−0.0003 (10)	−0.0007 (10)
C14	0.0285 (11)	0.0359 (12)	0.025 (2)	−0.0014 (9)	−0.0004 (10)	0.0001 (11)
C15	0.029 (2)	0.0372 (15)	0.0223 (17)	−0.0004 (9)	0.0003 (18)	−0.0018 (11)
O15	0.0486 (13)	0.042 (3)	0.0298 (15)	−0.009 (2)	−0.0143 (13)	0.0038 (15)
C111	0.039 (2)	0.0298 (12)	0.0281 (15)	0.0047 (16)	−0.0045 (14)	−0.0029 (12)
C112	0.044 (2)	0.0457 (17)	0.0367 (17)	0.009 (2)	0.0038 (18)	−0.0049 (14)
C113	0.043 (2)	0.0515 (18)	0.0495 (19)	0.022 (2)	0.001 (2)	−0.0030 (15)
C114	0.048 (3)	0.0431 (16)	0.0362 (15)	0.022 (2)	−0.0056 (18)	−0.0019 (12)
C115	0.052 (2)	0.037 (2)	0.0360 (15)	0.0212 (14)	0.0068 (16)	0.0023 (14)
C116	0.038 (2)	0.0346 (15)	0.0348 (17)	0.0109 (16)	0.0007 (17)	0.0014 (12)
N131	0.0268 (10)	0.028 (3)	0.0327 (17)	−0.0015 (8)	−0.0060 (8)	−0.004 (2)
C132	0.0303 (12)	0.024 (2)	0.027 (2)	−0.0012 (9)	−0.0014 (10)	−0.001 (2)
O132	0.0328 (11)	0.033 (2)	0.0354 (17)	0.0021 (9)	−0.0079 (9)	−0.0108 (17)
C133	0.0289 (11)	0.0257 (15)	0.0193 (15)	−0.0005 (10)	−0.0012 (10)	0.0050 (12)
C134	0.0317 (12)	0.034 (2)	0.027 (2)	−0.0014 (10)	−0.0037 (11)	0.000 (2)
C14A	0.0350 (12)	0.027 (2)	0.0229 (16)	−0.0007 (11)	0.0009 (11)	0.0029 (15)
C135	0.0439 (15)	0.0324 (18)	0.0231 (15)	−0.0007 (13)	0.0007 (12)	0.0007 (12)
C136	0.0518 (18)	0.0318 (18)	0.0281 (17)	0.0069 (14)	0.0032 (13)	−0.0009 (13)
C137	0.0445 (16)	0.037 (2)	0.0409 (19)	0.0123 (14)	0.0041 (13)	−0.0009 (17)
C138	0.0343 (13)	0.036 (4)	0.0390 (17)	0.0037 (14)	−0.0009 (11)	−0.002 (2)
C18A	0.0322 (12)	0.023 (2)	0.0275 (16)	−0.0015 (10)	0.0014 (10)	0.0025 (17)
C151	0.026 (3)	0.0386 (12)	0.0230 (14)	−0.0013 (13)	0.0020 (19)	0.0010 (10)
C152	0.0374 (13)	0.040 (2)	0.024 (2)	−0.0026 (16)	−0.0044 (15)	−0.0006 (18)
C153	0.0433 (17)	0.0399 (18)	0.028 (3)	−0.0019 (12)	−0.0034 (15)	0.0026 (19)
C154	0.031 (3)	0.0378 (14)	0.0372 (15)	−0.0070 (15)	0.0004 (14)	−0.0024 (11)
Cl15	0.0488 (9)	0.0455 (4)	0.0468 (11)	−0.0157 (5)	−0.0068 (7)	−0.0045 (7)
C155	0.029 (2)	0.0474 (18)	0.0392 (16)	−0.0030 (15)	−0.0100 (16)	0.0018 (14)
C156	0.029 (2)	0.0408 (15)	0.0308 (16)	0.0014 (13)	−0.0038 (15)	0.0042 (13)
Cl14	0.0732 (6)	0.0551 (5)	0.0359 (5)	0.0348 (4)	−0.0045 (4)	0.0033 (4)
C21	0.031 (2)	0.0329 (12)	0.0259 (15)	0.0002 (12)	−0.0011 (14)	−0.0022 (12)
O21	0.0361 (17)	0.0468 (14)	0.0286 (13)	0.0066 (13)	0.0035 (11)	−0.0023 (12)
C22	0.0338 (15)	0.0322 (13)	0.0231 (19)	0.0026 (10)	0.0013 (13)	0.0013 (11)
C23	0.0305 (12)	0.0298 (12)	0.0217 (15)	0.0013 (9)	−0.0003 (10)	−0.0007 (10)
C24	0.0285 (11)	0.0359 (12)	0.025 (2)	−0.0014 (9)	−0.0004 (10)	0.0001 (11)
C25	0.029 (2)	0.0372 (15)	0.0223 (17)	−0.0004 (9)	0.0003 (18)	−0.0018 (11)
O25	0.0486 (13)	0.042 (3)	0.0298 (15)	−0.009 (2)	−0.0143 (13)	0.0038 (15)
C211	0.039 (2)	0.0298 (12)	0.0281 (15)	0.0047 (16)	−0.0045 (14)	−0.0029 (12)
C212	0.044 (2)	0.0457 (17)	0.0367 (17)	0.009 (2)	0.0038 (18)	−0.0049 (14)
C213	0.043 (2)	0.0515 (18)	0.0495 (19)	0.022 (2)	0.001 (2)	−0.0030 (15)
C214	0.048 (3)	0.0431 (16)	0.0362 (15)	0.022 (2)	−0.0056 (18)	−0.0019 (12)
C215	0.052 (2)	0.037 (2)	0.0360 (15)	0.0212 (14)	0.0068 (16)	0.0023 (14)
C216	0.038 (2)	0.0346 (15)	0.0348 (17)	0.0109 (16)	0.0007 (17)	0.0014 (12)
N231	0.0268 (10)	0.028 (3)	0.0327 (17)	−0.0015 (8)	−0.0060 (8)	−0.004 (2)
C232	0.0303 (12)	0.024 (2)	0.027 (2)	−0.0012 (9)	−0.0014 (10)	−0.001 (2)
O232	0.0328 (11)	0.033 (2)	0.0354 (17)	0.0021 (9)	−0.0079 (9)	−0.0108 (17)
C233	0.0289 (11)	0.0257 (15)	0.0193 (15)	−0.0005 (10)	−0.0012 (10)	0.0050 (12)
C234	0.0317 (12)	0.034 (2)	0.027 (2)	−0.0014 (10)	−0.0037 (11)	0.000 (2)
C24A	0.0350 (12)	0.027 (2)	0.0229 (16)	−0.0007 (11)	0.0009 (11)	0.0029 (15)
C235	0.0439 (15)	0.0324 (18)	0.0231 (15)	−0.0007 (13)	0.0007 (12)	0.0007 (12)
C236	0.0518 (18)	0.0318 (18)	0.0281 (17)	0.0069 (14)	0.0032 (13)	−0.0009 (13)
C237	0.0445 (16)	0.037 (2)	0.0409 (19)	0.0123 (14)	0.0041 (13)	−0.0009 (17)
C238	0.0343 (13)	0.036 (4)	0.0390 (17)	0.0037 (14)	−0.0009 (11)	−0.002 (2)
C28A	0.0322 (12)	0.023 (2)	0.0275 (16)	−0.0015 (10)	0.0014 (10)	0.0025 (17)
C251	0.026 (3)	0.0386 (12)	0.0230 (14)	−0.0013 (13)	0.0020 (19)	0.0010 (10)
C252	0.0374 (13)	0.040 (2)	0.024 (2)	−0.0026 (16)	−0.0044 (15)	−0.0006 (18)
C253	0.0433 (17)	0.0399 (18)	0.028 (3)	−0.0019 (12)	−0.0034 (15)	0.0026 (19)
C254	0.031 (3)	0.0378 (14)	0.0372 (15)	−0.0070 (15)	0.0004 (14)	−0.0024 (11)
Cl25	0.0488 (9)	0.0455 (4)	0.0468 (11)	−0.0157 (5)	−0.0068 (7)	−0.0045 (7)
C255	0.029 (2)	0.0474 (18)	0.0392 (16)	−0.0030 (15)	−0.0100 (16)	0.0018 (14)
C256	0.029 (2)	0.0408 (15)	0.0308 (16)	0.0014 (13)	−0.0038 (15)	0.0042 (13)
Cl22	0.062 (3)	0.071 (4)	0.074 (4)	0.007 (3)	−0.004 (3)	−0.003 (3)

Geometric parameters (Å, º)

C11—O11	1.219 (3)	C21—O21	1.219 (5)
C11—C111	1.498 (4)	C21—C211	1.498 (6)
C11—C12	1.512 (3)	C21—C22	1.514 (5)
C12—C13	1.534 (3)	C22—C23	1.532 (6)
C12—H12A	0.9900	C22—H22A	0.9900
C12—H12B	0.9900	C22—H22B	0.9900
C13—C133	1.518 (3)	C23—C233	1.518 (5)
C13—C14	1.536 (3)	C23—C24	1.536 (5)
C13—H13	1.0000	C23—H23	1.0000
C14—C15	1.515 (3)	C24—C25	1.515 (5)
C14—H14A	0.9900	C24—H24A	0.9900
C14—H14B	0.9900	C24—H24B	0.9900
C15—O15	1.216 (3)	C25—O25	1.216 (6)
C15—C151	1.498 (3)	C25—C251	1.499 (5)
C111—C112	1.383 (4)	C211—C212	1.381 (6)
C111—C116	1.406 (4)	C211—C216	1.408 (6)
C112—C113	1.391 (4)	C212—C213	1.392 (6)
C112—H112	0.9500	C212—Cl22	1.700 (14)
C113—C114	1.382 (5)	C213—C214	1.384 (6)
C113—H113	0.9500	C213—H213	0.9500
C114—C115	1.376 (4)	C214—C215	1.374 (6)
C114—Cl14	1.747 (3)	C214—H214	0.9500
C115—C116	1.385 (4)	C215—C216	1.384 (6)
C115—H115	0.9500	C215—H215	0.9500
C116—H116	0.9500	C216—H216	0.9500
N131—C132	1.363 (3)	N231—C232	1.363 (5)
N131—C18A	1.386 (3)	N231—C28A	1.385 (5)
N131—H131	0.8800	N231—H231	0.8800
C132—O132	1.251 (3)	C232—O232	1.252 (5)
C132—C133	1.466 (3)	C232—C233	1.467 (5)
C133—C134	1.356 (3)	C233—C234	1.357 (5)
C134—C14A	1.427 (3)	C234—C24A	1.427 (5)
C134—H134	0.9500	C234—H234	0.9500
C14A—C18A	1.402 (3)	C24A—C28A	1.403 (5)
C14A—C135	1.414 (4)	C24A—C235	1.413 (5)
C135—C136	1.374 (4)	C235—C236	1.374 (6)
C135—H135	0.9500	C235—H235	0.9500
C136—C137	1.397 (4)	C236—C237	1.397 (6)
C136—H136	0.9500	C236—H236	0.9500
C137—C138	1.376 (4)	C237—C238	1.376 (6)
C137—H137	0.9500	C237—H237	0.9500
C138—C18A	1.400 (4)	C238—C28A	1.400 (6)
C138—H138	0.9500	C238—H238	0.9500
C151—C156	1.398 (4)	C251—C256	1.399 (5)
C151—C152	1.408 (5)	C251—C252	1.408 (6)
C152—C153	1.384 (4)	C252—C253	1.384 (6)
C152—H152	0.9500	C252—H252	0.9500
C153—C154	1.392 (5)	C253—C254	1.392 (6)
C153—H153	0.9500	C253—H253	0.9500
C154—C155	1.380 (4)	C254—C255	1.381 (6)
C154—Cl15	1.748 (3)	C254—Cl25	1.749 (5)
C155—C156	1.390 (4)	C255—C256	1.389 (6)
C155—H155	0.9500	C255—H255	0.9500
C156—H156	0.9500	C256—H256	0.9500
O11—C11—C111	121.1 (3)	O21—C21—C211	121.2 (8)
O11—C11—C12	122.3 (3)	O21—C21—C22	121.7 (7)
C111—C11—C12	116.6 (2)	C211—C21—C22	116.6 (7)
C11—C12—C13	115.3 (2)	C21—C22—C23	115.8 (7)
C11—C12—H12A	108.4	C21—C22—H22A	108.3
C13—C12—H12A	108.4	C23—C22—H22A	108.3
C11—C12—H12B	108.4	C21—C22—H22B	108.3
C13—C12—H12B	108.4	C23—C22—H22B	108.3
H12A—C12—H12B	107.5	H22A—C22—H22B	107.4
C133—C13—C12	107.4 (2)	C233—C23—C22	107.9 (7)
C133—C13—C14	112.1 (2)	C233—C23—C24	112.2 (7)
C12—C13—C14	110.6 (2)	C22—C23—C24	110.5 (7)
C133—C13—H13	108.9	C233—C23—H23	108.7
C12—C13—H13	108.9	C22—C23—H23	108.7
C14—C13—H13	108.9	C24—C23—H23	108.7
C15—C14—C13	113.1 (2)	C25—C24—C23	113.3 (7)
C15—C14—H14A	109.0	C25—C24—H24A	108.9
C13—C14—H14A	109.0	C23—C24—H24A	108.9
C15—C14—H14B	109.0	C25—C24—H24B	108.9
C13—C14—H14B	109.0	C23—C24—H24B	108.9
H14A—C14—H14B	107.8	H24A—C24—H24B	107.7
O15—C15—C151	120.4 (3)	O25—C25—C251	120.4 (8)
O15—C15—C14	121.3 (2)	O25—C25—C24	121.2 (8)
C151—C15—C14	118.3 (2)	C251—C25—C24	118.0 (6)
C112—C111—C116	119.1 (3)	C212—C211—C216	118.5 (6)
C112—C111—C11	119.5 (3)	C212—C211—C21	120.3 (6)
C116—C111—C11	121.3 (3)	C216—C211—C21	120.9 (7)
C111—C112—C113	120.7 (3)	C211—C212—C213	121.3 (6)
C111—C112—H112	119.6	C211—C212—Cl22	128.8 (11)
C113—C112—H112	119.6	C213—C212—Cl22	109.1 (11)
C114—C113—C112	118.5 (3)	C214—C213—C212	118.0 (7)
C114—C113—H113	120.7	C214—C213—H213	121.0
C112—C113—H113	120.7	C212—C213—H213	121.0
C115—C114—C113	122.5 (3)	C215—C214—C213	122.1 (7)
C115—C114—Cl14	119.5 (3)	C215—C214—H214	118.9
C113—C114—Cl14	118.0 (2)	C213—C214—H214	118.9
C114—C115—C116	118.4 (3)	C214—C215—C216	118.5 (7)
C114—C115—H115	120.8	C214—C215—H215	120.8
C116—C115—H115	120.8	C216—C215—H215	120.8
C115—C116—C111	120.7 (3)	C215—C216—C211	120.3 (7)
C115—C116—H116	119.7	C215—C216—H216	119.8
C111—C116—H116	119.7	C211—C216—H216	119.8
C132—N131—C18A	125.1 (2)	C232—N231—C28A	125.3 (6)
C132—N131—H131	117.5	C232—N231—H231	117.3
C18A—N131—H131	117.5	C28A—N231—H231	117.3
O132—C132—N131	120.4 (3)	O232—C232—N231	120.4 (7)
O132—C132—C133	123.5 (2)	O232—C232—C233	123.3 (8)
N131—C132—C133	116.1 (2)	N231—C232—C233	116.1 (5)
C134—C133—C132	119.4 (2)	C234—C233—C232	119.1 (6)
C134—C133—C13	122.3 (2)	C234—C233—C23	122.6 (6)
C132—C133—C13	118.0 (2)	C232—C233—C23	117.9 (6)
C133—C134—C14A	122.7 (2)	C233—C234—C24A	122.8 (6)
C133—C134—H134	118.7	C233—C234—H234	118.6
C14A—C134—H134	118.7	C24A—C234—H234	117.0
C18A—C14A—C135	119.0 (2)	C28A—C24A—C235	118.7 (5)
C18A—C14A—C134	117.6 (2)	C28A—C24A—C234	117.4 (5)
C135—C14A—C134	123.4 (2)	C235—C24A—C234	123.8 (6)
C136—C135—C14A	119.9 (3)	C236—C235—C24A	120.2 (6)
C136—C135—H135	120.0	C236—C235—H235	119.9
C14A—C135—H135	120.0	C24A—C235—H235	119.9
C135—C136—C137	120.3 (3)	C235—C236—C237	120.1 (6)
C135—C136—H136	119.8	C235—C236—H236	119.9
C137—C136—H136	119.8	C237—C236—H236	119.9
C138—C137—C136	120.9 (3)	C238—C237—C236	120.9 (6)
C138—C137—H137	119.5	C238—C237—H237	119.6
C136—C137—H137	119.5	C236—C237—H237	119.6
C137—C138—C18A	119.2 (3)	C237—C238—C28A	119.3 (7)
C137—C138—H138	120.4	C237—C238—H238	120.4
C18A—C138—H138	120.4	C28A—C238—H238	120.4
N131—C18A—C138	120.5 (2)	N231—C28A—C238	120.8 (6)
N131—C18A—C14A	119.0 (2)	N231—C28A—C24A	118.7 (5)
C138—C18A—C14A	120.5 (2)	C238—C28A—C24A	120.3 (6)
C156—C151—C152	119.3 (3)	C256—C251—C252	119.2 (6)
C156—C151—C15	122.6 (3)	C256—C251—C25	122.2 (6)
C152—C151—C15	118.0 (3)	C252—C251—C25	118.3 (7)
C153—C152—C151	121.0 (3)	C253—C252—C251	121.0 (7)
C153—C152—H152	119.5	C253—C252—H252	119.5
C151—C152—H152	119.5	C251—C252—H252	119.5
C152—C153—C154	118.0 (3)	C252—C253—C254	118.2 (6)
C152—C153—H153	121.0	C252—C253—H253	120.9
C154—C153—H153	121.0	C254—C253—H253	120.9
C155—C154—C153	122.3 (3)	C255—C254—C253	122.0 (6)
C155—C154—Cl15	119.1 (2)	C255—C254—Cl25	118.8 (7)
C153—C154—Cl15	118.6 (2)	C253—C254—Cl25	118.4 (8)
C154—C155—C156	119.4 (3)	C254—C255—C256	119.5 (6)
C154—C155—H155	120.3	C254—C255—H255	120.3
C156—C155—H155	120.3	C256—C255—H255	120.3
C155—C156—C151	119.8 (3)	C255—C256—C251	119.9 (6)
C155—C156—H156	120.1	C255—C256—H256	120.0
C151—C156—H156	120.1	C251—C256—H256	120.0
O11—C11—C12—C13	−21.8 (8)	C211—C21—C22—C23	160 (3)
C111—C11—C12—C13	160.3 (4)	C21—C22—C23—C233	172 (2)
C11—C12—C13—C133	174.8 (4)	C21—C22—C23—C24	−65 (3)
C11—C12—C13—C14	−62.6 (4)	C233—C23—C24—C25	−64 (4)
C133—C13—C14—C15	−63.3 (6)	C22—C23—C24—C25	175 (3)
C12—C13—C14—C15	176.9 (6)	C23—C24—C25—O25	−21 (8)
C13—C14—C15—O15	−14.9 (14)	C23—C24—C25—C251	166 (4)
C13—C14—C15—C151	164.6 (7)	O21—C21—C211—C212	4 (6)
O11—C11—C111—C112	14.1 (8)	C22—C21—C211—C212	−168 (4)
C12—C11—C111—C112	−167.9 (5)	O21—C21—C211—C216	−170 (4)
O11—C11—C111—C116	−166.6 (6)	C22—C21—C211—C216	18 (5)
C12—C11—C111—C116	11.4 (8)	C216—C211—C212—C213	−4 (6)
C116—C111—C112—C113	−0.6 (8)	C21—C211—C212—C213	−179 (4)
C11—C111—C112—C113	178.7 (6)	C216—C211—C212—Cl22	−173 (3)
C111—C112—C113—C114	0.1 (9)	C21—C211—C212—Cl22	13 (6)
C112—C113—C114—C115	0.1 (9)	C211—C212—C213—C214	5 (6)
C112—C113—C114—Cl14	−178.4 (5)	Cl22—C212—C213—C214	176 (3)
C113—C114—C115—C116	0.4 (9)	C212—C213—C214—C215	3 (6)
Cl14—C114—C115—C116	178.8 (4)	C213—C214—C215—C216	−11 (5)
C114—C115—C116—C111	−1.0 (8)	C214—C215—C216—C211	12 (5)
C112—C111—C116—C115	1.1 (8)	C212—C211—C216—C215	−4 (5)
C11—C111—C116—C115	−178.2 (5)	C21—C211—C216—C215	170 (3)
C18A—N131—C132—O132	179.9 (9)	C28A—N231—C232—O232	174 (6)
C18A—N131—C132—C133	−0.8 (15)	C28A—N231—C232—C233	−1 (10)
O132—C132—C133—C134	−176.7 (8)	O232—C232—C233—C234	−179 (5)
N131—C132—C133—C134	4.0 (11)	N231—C232—C233—C234	−4 (7)
O132—C132—C133—C13	−2.2 (10)	O232—C232—C233—C23	8 (7)
N131—C132—C133—C13	178.5 (7)	N231—C232—C233—C23	−176 (5)
C12—C13—C133—C134	78.9 (6)	C22—C23—C233—C234	83 (4)
C14—C13—C133—C134	−42.8 (6)	C24—C23—C233—C234	−39 (4)
C12—C13—C133—C132	−95.5 (5)	C22—C23—C233—C232	−105 (3)
C14—C13—C133—C132	142.8 (5)	C24—C23—C233—C232	133 (3)
C132—C133—C134—C14A	−4.9 (10)	C232—C233—C234—C24A	8 (7)
C13—C133—C134—C14A	−179.3 (5)	C23—C233—C234—C24A	−180 (4)
C133—C134—C14A—C18A	2.5 (10)	C233—C234—C24A—C28A	−8 (7)
C133—C134—C14A—C135	−174.4 (5)	C233—C234—C24A—C235	173 (4)
C18A—C14A—C135—C136	−0.3 (5)	C28A—C24A—C235—C236	−4 (4)
C134—C14A—C135—C136	176.6 (5)	C234—C24A—C235—C236	176 (4)
C14A—C135—C136—C137	1.6 (5)	C24A—C235—C236—C237	1 (4)
C135—C136—C137—C138	−0.8 (9)	C235—C236—C237—C238	−2 (6)
C136—C137—C138—C18A	−1.4 (15)	C236—C237—C238—C28A	5 (10)
C132—N131—C18A—C138	178.2 (11)	C232—N231—C28A—C238	177 (7)
C132—N131—C18A—C14A	−1.5 (15)	C232—N231—C28A—C24A	1 (10)
C137—C138—C18A—N131	−176.9 (10)	C237—C238—C28A—N231	177 (6)
C137—C138—C18A—C14A	2.7 (15)	C237—C238—C28A—C24A	−8 (10)
C135—C14A—C18A—N131	177.8 (7)	C235—C24A—C28A—N231	−178 (5)
C134—C14A—C18A—N131	0.7 (9)	C234—C24A—C28A—N231	3 (7)
C135—C14A—C18A—C138	−1.9 (9)	C235—C24A—C28A—C238	7 (7)
C134—C14A—C18A—C138	−179.0 (9)	C234—C24A—C28A—C238	−172 (6)
O15—C15—C151—C156	−171.0 (13)	O25—C25—C251—C256	−172 (8)
C14—C15—C151—C156	9.5 (14)	C24—C25—C251—C256	1 (9)
O15—C15—C151—C152	10.8 (16)	O25—C25—C251—C252	2 (10)
C14—C15—C151—C152	−168.8 (9)	C24—C25—C251—C252	175 (6)
C156—C151—C152—C153	3.3 (15)	C256—C251—C252—C253	−6 (10)
C15—C151—C152—C153	−178.4 (9)	C25—C251—C252—C253	−180 (6)
C151—C152—C153—C154	0.0 (13)	C251—C252—C253—C254	4 (9)
C152—C153—C154—C155	−2.9 (12)	C252—C253—C254—C255	−1 (8)
C152—C153—C154—Cl15	178.5 (8)	C252—C253—C254—Cl25	169 (5)
C153—C154—C155—C156	2.3 (10)	C253—C254—C255—C256	−1 (6)
Cl15—C154—C155—C156	−179.0 (4)	Cl25—C254—C255—C256	−171 (3)
C154—C155—C156—C151	1.1 (8)	C254—C255—C256—C251	0 (6)
C152—C151—C156—C155	−3.9 (12)	C252—C251—C256—C255	3 (8)
C15—C151—C156—C155	177.9 (7)	C25—C251—C256—C255	177 (5)
O21—C21—C22—C23	−11 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N131—H131···O132^i	0.88	1.96	2.840 (7)	175
C156—H156···O15^ii	0.95	2.46	3.386 (12)	165
C12—H12A···O11^ii	0.99	2.56	3.451 (5)	149
N231—H231···O232^i	0.88	2.20	3.07 (5)	168
C256—H256···O25^ii	0.95	2.46	3.41 (7)	176
C22—H22A···O21^ii	0.99	2.58	3.42 (3)	142

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) y+1/4, −x+5/4, z+1/4.

(II) (9RS,10RS)-8,9-bis(4-chlorobenzyl)- 10-(2-oxo-1,2-dihydroquinolin-3-yl)-5,6,9,10-tetrahydrophenanthridine

Crystal data

C36H22Cl2N2O4	Z = 2
Mr = 617.46	F(000) = 636
Triclinic, P1	Dx = 1.195 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6771 (19) Å	Cell parameters from 7841 reflections
b = 11.5208 (15) Å	θ = 2.7–27.5°
c = 15.7275 (13) Å	µ = 0.23 mm^−1
α = 83.956 (11)°	T = 120 K
β = 72.795 (13)°	Block, pale yellow
γ = 68.204 (14)°	0.34 × 0.31 × 0.18 mm
V = 1715.9 (5) Å^3

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	7841 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	5593 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.7°
ϕ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −14→14
Tmin = 0.932, Tmax = 0.960	l = 0→20
7841 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.161	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0973P)^2] where P = (Fo^2 + 2Fc^2)/3
7841 reflections	(Δ/σ)max = 0.001
397 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.48 e Å^−3

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

	x	y	z	Uiso*/Ueq
C1	0.75955 (19)	0.42859 (18)	0.02159 (12)	0.0271 (4)
H1	0.8065	0.4662	0.0463	0.033*
C2	0.8076 (2)	0.39849 (19)	−0.06735 (12)	0.0308 (4)
H2	0.8869	0.4161	−0.1039	0.037*
C3	0.7399 (2)	0.3419 (2)	−0.10447 (13)	0.0323 (5)
H3	0.7740	0.3207	−0.1660	0.039*
C4	0.6246 (2)	0.31674 (19)	−0.05245 (12)	0.0298 (4)
H4	0.5794	0.2782	−0.0780	0.036*
C4A	0.57403 (18)	0.34781 (17)	0.03778 (12)	0.0239 (4)
N5	0.45736 (15)	0.32377 (14)	0.08975 (10)	0.0246 (3)
H5	0.4194	0.2869	0.0637	0.030*
C6	0.39607 (18)	0.35195 (17)	0.17742 (11)	0.0225 (4)
O6	0.29007 (13)	0.32697 (13)	0.21880 (8)	0.0294 (3)
C6A	0.46398 (18)	0.41083 (16)	0.21851 (11)	0.0220 (4)
C7	0.40159 (18)	0.44173 (17)	0.31270 (11)	0.0227 (4)
H7	0.3299	0.4115	0.3459	0.027*
C8	0.44237 (18)	0.51195 (17)	0.35428 (12)	0.0242 (4)
C9	0.54800 (18)	0.56927 (17)	0.30186 (12)	0.0244 (4)
H9	0.6034	0.5757	0.3413	0.029*
C10	0.65236 (18)	0.49052 (17)	0.21735 (12)	0.0234 (4)
H10	0.6894	0.5484	0.1744	0.028*
C10A	0.58135 (17)	0.43499 (16)	0.17088 (11)	0.0210 (4)
C10B	0.64060 (18)	0.40407 (17)	0.07699 (12)	0.0231 (4)
C87	0.36718 (19)	0.55639 (19)	0.44707 (12)	0.0286 (4)
O87	0.38155 (15)	0.64457 (15)	0.47544 (10)	0.0399 (4)
C81	0.2682 (2)	0.4957 (2)	0.50289 (12)	0.0289 (4)
C82	0.1319 (2)	0.5728 (2)	0.54833 (12)	0.0323 (5)
H82	0.1064	0.6611	0.5451	0.039*
C83	0.0348 (2)	0.5218 (2)	0.59758 (13)	0.0334 (5)
H83	−0.0576	0.5742	0.6276	0.040*
C84	0.0740 (2)	0.3937 (2)	0.60257 (12)	0.0352 (5)
Cl84	−0.04932 (6)	0.32789 (6)	0.66187 (4)	0.04772 (18)
C85	0.2093 (2)	0.3147 (2)	0.56020 (13)	0.0361 (5)
H85	0.2353	0.2265	0.5657	0.043*
C86	0.3055 (2)	0.3671 (2)	0.50985 (13)	0.0326 (5)
H86	0.3977	0.3144	0.4799	0.039*
C97	0.47088 (19)	0.70125 (18)	0.27227 (12)	0.0265 (4)
O97	0.35032 (14)	0.73178 (13)	0.26828 (10)	0.0359 (3)
C91	0.54745 (19)	0.79065 (17)	0.24530 (12)	0.0252 (4)
C92	0.4770 (2)	0.90752 (19)	0.21449 (14)	0.0342 (5)
H92	0.3837	0.9270	0.2116	0.041*
C93	0.5395 (2)	0.9955 (2)	0.18806 (15)	0.0376 (5)
H93	0.4900	1.0750	0.1675	0.045*
C94	0.6748 (2)	0.96637 (19)	0.19185 (13)	0.0321 (4)
Cl94	0.75451 (6)	1.07734 (5)	0.15721 (4)	0.04727 (18)
C95	0.7491 (2)	0.85151 (19)	0.22133 (14)	0.0334 (5)
H95	0.8426	0.8331	0.2235	0.040*
C96	0.6855 (2)	0.76338 (18)	0.24783 (13)	0.0298 (4)
H96	0.7359	0.6838	0.2679	0.036*
N101	1.02403 (15)	0.31428 (14)	0.23040 (10)	0.0254 (3)
H101	1.1070	0.3215	0.2103	0.030*
C102	0.91336 (19)	0.40625 (17)	0.20727 (12)	0.0258 (4)
O102	0.93055 (14)	0.49608 (13)	0.16202 (10)	0.0379 (4)
C103	0.77753 (18)	0.38800 (17)	0.23959 (12)	0.0226 (4)
C104	0.76772 (19)	0.28607 (18)	0.28794 (12)	0.0257 (4)
H104	0.6797	0.2750	0.3068	0.031*
C14A	0.88584 (19)	0.19385 (18)	0.31180 (12)	0.0269 (4)
C105	0.8776 (2)	0.0889 (2)	0.36401 (14)	0.0374 (5)
H105	0.7912	0.0752	0.3837	0.045*
C106	0.9940 (2)	0.0057 (2)	0.38701 (16)	0.0446 (6)
H106	0.9876	−0.0653	0.4222	0.053*
C107	1.1204 (2)	0.0257 (2)	0.35868 (15)	0.0418 (5)
H107	1.1998	−0.0320	0.3750	0.050*
C108	1.1331 (2)	0.1276 (2)	0.30735 (13)	0.0332 (5)
H108	1.2200	0.1405	0.2891	0.040*
C18A	1.01583 (19)	0.21189 (18)	0.28235 (12)	0.0250 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0225 (9)	0.0297 (10)	0.0290 (10)	−0.0120 (8)	−0.0048 (8)	0.0041 (8)
C2	0.0226 (9)	0.0389 (11)	0.0273 (10)	−0.0137 (9)	0.0001 (8)	0.0048 (8)
C3	0.0301 (10)	0.0399 (12)	0.0223 (9)	−0.0122 (9)	−0.0015 (8)	0.0011 (8)
C4	0.0274 (10)	0.0376 (11)	0.0273 (10)	−0.0133 (9)	−0.0101 (8)	0.0016 (8)
C4A	0.0182 (8)	0.0256 (9)	0.0265 (9)	−0.0079 (7)	−0.0054 (7)	0.0035 (7)
N5	0.0205 (8)	0.0305 (9)	0.0251 (8)	−0.0116 (7)	−0.0056 (6)	−0.0021 (6)
C6	0.0169 (8)	0.0251 (9)	0.0251 (9)	−0.0066 (7)	−0.0077 (7)	0.0033 (7)
O6	0.0213 (7)	0.0415 (8)	0.0295 (7)	−0.0182 (6)	−0.0037 (5)	−0.0013 (6)
C6A	0.0183 (9)	0.0238 (9)	0.0240 (9)	−0.0086 (7)	−0.0055 (7)	0.0028 (7)
C7	0.0153 (8)	0.0284 (10)	0.0238 (9)	−0.0082 (7)	−0.0046 (7)	0.0019 (7)
C8	0.0166 (9)	0.0271 (10)	0.0267 (9)	−0.0071 (7)	−0.0036 (7)	0.0001 (7)
C9	0.0200 (9)	0.0274 (10)	0.0271 (9)	−0.0112 (8)	−0.0053 (7)	0.0005 (7)
C10	0.0177 (8)	0.0248 (9)	0.0289 (9)	−0.0110 (7)	−0.0043 (7)	0.0018 (7)
C10A	0.0159 (8)	0.0221 (9)	0.0249 (9)	−0.0071 (7)	−0.0059 (7)	0.0033 (7)
C10B	0.0188 (9)	0.0230 (9)	0.0258 (9)	−0.0072 (7)	−0.0050 (7)	0.0031 (7)
C87	0.0209 (9)	0.0373 (11)	0.0278 (10)	−0.0109 (8)	−0.0060 (8)	−0.0016 (8)
O87	0.0326 (8)	0.0494 (10)	0.0412 (8)	−0.0209 (7)	−0.0024 (6)	−0.0146 (7)
C81	0.0239 (9)	0.0456 (12)	0.0203 (9)	−0.0155 (9)	−0.0050 (7)	−0.0045 (8)
C82	0.0250 (10)	0.0472 (13)	0.0259 (10)	−0.0142 (9)	−0.0035 (8)	−0.0109 (9)
C83	0.0251 (10)	0.0526 (14)	0.0232 (9)	−0.0162 (10)	−0.0014 (8)	−0.0089 (9)
C84	0.0274 (10)	0.0594 (15)	0.0208 (9)	−0.0203 (10)	−0.0046 (8)	0.0037 (9)
Cl84	0.0370 (3)	0.0655 (4)	0.0386 (3)	−0.0266 (3)	−0.0011 (2)	0.0130 (3)
C85	0.0328 (11)	0.0443 (13)	0.0291 (10)	−0.0147 (10)	−0.0067 (9)	0.0070 (9)
C86	0.0239 (10)	0.0432 (12)	0.0265 (10)	−0.0093 (9)	−0.0055 (8)	0.0031 (8)
C97	0.0225 (9)	0.0303 (10)	0.0252 (9)	−0.0066 (8)	−0.0067 (7)	−0.0038 (7)
O97	0.0255 (7)	0.0344 (8)	0.0511 (9)	−0.0103 (6)	−0.0168 (6)	0.0031 (6)
C91	0.0248 (9)	0.0247 (9)	0.0257 (9)	−0.0087 (8)	−0.0061 (8)	−0.0012 (7)
C92	0.0266 (10)	0.0311 (11)	0.0409 (11)	−0.0069 (9)	−0.0083 (9)	0.0011 (9)
C93	0.0377 (12)	0.0271 (11)	0.0456 (12)	−0.0101 (9)	−0.0115 (10)	0.0046 (9)
C94	0.0381 (11)	0.0262 (10)	0.0357 (11)	−0.0164 (9)	−0.0086 (9)	−0.0014 (8)
Cl94	0.0536 (4)	0.0356 (3)	0.0624 (4)	−0.0281 (3)	−0.0170 (3)	0.0075 (3)
C95	0.0332 (11)	0.0332 (11)	0.0406 (11)	−0.0165 (9)	−0.0145 (9)	0.0008 (9)
C96	0.0315 (10)	0.0258 (10)	0.0359 (11)	−0.0108 (8)	−0.0153 (9)	0.0027 (8)
N101	0.0142 (7)	0.0291 (8)	0.0337 (8)	−0.0090 (6)	−0.0051 (6)	−0.0032 (7)
C102	0.0206 (9)	0.0269 (10)	0.0312 (10)	−0.0112 (8)	−0.0054 (7)	−0.0012 (8)
O102	0.0254 (7)	0.0344 (8)	0.0557 (9)	−0.0170 (6)	−0.0095 (7)	0.0112 (7)
C103	0.0193 (9)	0.0255 (9)	0.0257 (9)	−0.0102 (7)	−0.0067 (7)	−0.0013 (7)
C104	0.0205 (9)	0.0294 (10)	0.0291 (9)	−0.0112 (8)	−0.0064 (7)	−0.0003 (8)
C14A	0.0233 (9)	0.0283 (10)	0.0284 (10)	−0.0090 (8)	−0.0054 (8)	−0.0027 (8)
C105	0.0325 (11)	0.0382 (12)	0.0414 (12)	−0.0152 (10)	−0.0096 (9)	0.0080 (9)
C106	0.0439 (13)	0.0409 (13)	0.0480 (13)	−0.0159 (11)	−0.0163 (11)	0.0173 (10)
C107	0.0326 (12)	0.0432 (13)	0.0425 (12)	−0.0038 (10)	−0.0145 (10)	0.0056 (10)
C108	0.0232 (10)	0.0383 (12)	0.0342 (11)	−0.0065 (9)	−0.0069 (8)	−0.0034 (9)
C18A	0.0208 (9)	0.0283 (10)	0.0253 (9)	−0.0074 (8)	−0.0054 (7)	−0.0048 (7)

Geometric parameters (Å, º)

C1—C2	1.373 (3)	C84—C85	1.393 (3)
C1—C10B	1.418 (2)	C84—Cl84	1.745 (2)
C1—H1	0.9500	C85—C86	1.388 (3)
C2—C3	1.403 (3)	C85—H85	0.9500
C2—H2	0.9500	C86—H86	0.9500
C3—C4	1.374 (3)	C97—O97	1.221 (2)
C3—H3	0.9500	C97—C91	1.496 (3)
C4—C4A	1.394 (3)	C91—C92	1.393 (3)
C4—H4	0.9500	C91—C96	1.400 (3)
C4A—N5	1.379 (2)	C92—C93	1.377 (3)
C4A—C10B	1.411 (3)	C92—H92	0.9500
N5—C6	1.355 (2)	C93—C94	1.374 (3)
N5—H5	0.8800	C93—H93	0.9500
C6—O6	1.247 (2)	C94—C95	1.380 (3)
C6—C6A	1.462 (3)	C94—Cl94	1.744 (2)
C6A—C10A	1.367 (2)	C95—C96	1.386 (3)
C6A—C7	1.455 (2)	C95—H95	0.9500
C7—C8	1.346 (3)	C96—H96	0.9500
C7—H7	0.9500	N101—C102	1.377 (2)
C8—C87	1.482 (3)	N101—C18A	1.378 (2)
C8—C9	1.509 (2)	N101—H101	0.8800
C9—C97	1.534 (3)	C102—O102	1.233 (2)
C9—C10	1.568 (3)	C102—C103	1.474 (2)
C9—H9	1.0000	C103—C104	1.351 (3)
C10—C10A	1.518 (3)	C104—C14A	1.436 (3)
C10—C103	1.523 (2)	C104—H104	0.9500
C10—H10	1.0000	C14A—C105	1.403 (3)
C10A—C10B	1.449 (2)	C14A—C18A	1.413 (3)
C87—O87	1.227 (2)	C105—C106	1.379 (3)
C87—C81	1.499 (3)	C105—H105	0.9500
C81—C86	1.385 (3)	C106—C107	1.388 (3)
C81—C82	1.406 (3)	C106—H106	0.9500
C82—C83	1.379 (3)	C107—C108	1.379 (3)
C82—H82	0.9500	C107—H107	0.9500
C83—C84	1.377 (3)	C108—C18A	1.405 (3)
C83—H83	0.9500	C108—H108	0.9500
C2—C1—C10B	120.72 (18)	C83—C84—C85	121.77 (19)
C2—C1—H1	119.6	C83—C84—Cl84	119.37 (16)
C10B—C1—H1	119.6	C85—C84—Cl84	118.86 (18)
C1—C2—C3	120.19 (17)	C86—C85—C84	118.8 (2)
C1—C2—H2	119.9	C86—C85—H85	120.6
C3—C2—H2	119.9	C84—C85—H85	120.6
C4—C3—C2	120.42 (18)	C81—C86—C85	120.58 (19)
C4—C3—H3	119.8	C81—C86—H86	119.7
C2—C3—H3	119.8	C85—C86—H86	119.7
C3—C4—C4A	119.98 (18)	O97—C97—C91	120.43 (17)
C3—C4—H4	120.0	O97—C97—C9	120.64 (17)
C4A—C4—H4	120.0	C91—C97—C9	118.90 (15)
N5—C4A—C4	119.93 (17)	C92—C91—C96	118.33 (18)
N5—C4A—C10B	119.26 (16)	C92—C91—C97	117.51 (17)
C4—C4A—C10B	120.81 (16)	C96—C91—C97	124.15 (17)
C6—N5—C4A	125.69 (16)	C93—C92—C91	121.42 (19)
C6—N5—H5	117.2	C93—C92—H92	119.3
C4A—N5—H5	117.2	C91—C92—H92	119.3
O6—C6—N5	121.03 (16)	C94—C93—C92	118.94 (19)
O6—C6—C6A	123.56 (16)	C94—C93—H93	120.5
N5—C6—C6A	115.41 (15)	C92—C93—H93	120.5
C10A—C6A—C7	121.42 (16)	C93—C94—C95	121.69 (19)
C10A—C6A—C6	121.62 (16)	C93—C94—Cl94	118.85 (16)
C7—C6A—C6	116.96 (15)	C95—C94—Cl94	119.46 (16)
C8—C7—C6A	121.96 (16)	C94—C95—C96	119.07 (19)
C8—C7—H7	119.0	C94—C95—H95	120.5
C6A—C7—H7	119.0	C96—C95—H95	120.5
C7—C8—C87	121.85 (16)	C95—C96—C91	120.55 (18)
C7—C8—C9	120.10 (16)	C95—C96—H96	119.7
C87—C8—C9	116.95 (16)	C91—C96—H96	119.7
C8—C9—C97	109.56 (15)	C102—N101—C18A	125.47 (15)
C8—C9—C10	112.83 (15)	C102—N101—H101	117.3
C97—C9—C10	108.67 (14)	C18A—N101—H101	117.3
C8—C9—H9	108.6	O102—C102—N101	120.72 (16)
C97—C9—H9	108.6	O102—C102—C103	123.87 (17)
C10—C9—H9	108.6	N101—C102—C103	115.41 (16)
C10A—C10—C103	110.19 (14)	C104—C103—C102	120.28 (17)
C10A—C10—C9	112.59 (14)	C104—C103—C10	123.25 (16)
C103—C10—C9	111.59 (15)	C102—C103—C10	116.45 (15)
C10A—C10—H10	107.4	C103—C104—C14A	122.19 (17)
C103—C10—H10	107.4	C103—C104—H104	118.9
C9—C10—H10	107.4	C14A—C104—H104	118.9
C6A—C10A—C10B	120.23 (16)	C105—C14A—C18A	118.83 (18)
C6A—C10A—C10	119.77 (15)	C105—C14A—C104	123.34 (18)
C10B—C10A—C10	119.97 (15)	C18A—C14A—C104	117.82 (17)
C4A—C10B—C1	117.88 (16)	C106—C105—C14A	120.6 (2)
C4A—C10B—C10A	117.77 (15)	C106—C105—H105	119.7
C1—C10B—C10A	124.34 (16)	C14A—C105—H105	119.7
O87—C87—C8	120.21 (17)	C105—C106—C107	119.9 (2)
O87—C87—C81	121.36 (17)	C105—C106—H106	120.1
C8—C87—C81	118.35 (17)	C107—C106—H106	120.1
C86—C81—C82	119.19 (18)	C108—C107—C106	121.5 (2)
C86—C81—C87	122.42 (17)	C108—C107—H107	119.3
C82—C81—C87	118.38 (19)	C106—C107—H107	119.3
C83—C82—C81	120.8 (2)	C107—C108—C18A	119.10 (19)
C83—C82—H82	119.6	C107—C108—H108	120.4
C81—C82—H82	119.6	C18A—C108—H108	120.4
C84—C83—C82	118.90 (19)	N101—C18A—C108	121.13 (17)
C84—C83—H83	120.6	N101—C18A—C14A	118.76 (16)
C82—C83—H83	120.6	C108—C18A—C14A	120.10 (18)
C10B—C1—C2—C3	−0.6 (3)	C81—C82—C83—C84	0.8 (3)
C1—C2—C3—C4	0.4 (3)	C82—C83—C84—C85	0.8 (3)
C2—C3—C4—C4A	0.1 (3)	C82—C83—C84—Cl84	−178.06 (14)
C3—C4—C4A—N5	179.31 (18)	C83—C84—C85—C86	−1.7 (3)
C3—C4—C4A—C10B	−0.6 (3)	Cl84—C84—C85—C86	177.21 (15)
C4—C4A—N5—C6	−178.39 (17)	C82—C81—C86—C85	0.7 (3)
C10B—C4A—N5—C6	1.5 (3)	C87—C81—C86—C85	−178.10 (17)
C4A—N5—C6—O6	179.65 (17)	C84—C85—C86—C81	0.9 (3)
C4A—N5—C6—C6A	−1.2 (3)	C8—C9—C97—O97	−21.2 (2)
O6—C6—C6A—C10A	179.07 (17)	C10—C9—C97—O97	102.45 (19)
N5—C6—C6A—C10A	−0.1 (2)	C8—C9—C97—C91	160.87 (15)
O6—C6—C6A—C7	−0.5 (3)	C10—C9—C97—C91	−75.44 (19)
N5—C6—C6A—C7	−179.64 (15)	O97—C97—C91—C92	−1.1 (3)
C10A—C6A—C7—C8	10.3 (3)	C9—C97—C91—C92	176.81 (16)
C6—C6A—C7—C8	−170.20 (16)	O97—C97—C91—C96	179.97 (18)
C6A—C7—C8—C87	172.30 (17)	C9—C97—C91—C96	−2.1 (3)
C6A—C7—C8—C9	4.6 (3)	C96—C91—C92—C93	−0.8 (3)
C7—C8—C9—C97	92.2 (2)	C97—C91—C92—C93	−179.85 (18)
C87—C8—C9—C97	−76.08 (19)	C91—C92—C93—C94	0.4 (3)
C7—C8—C9—C10	−29.0 (2)	C92—C93—C94—C95	0.0 (3)
C87—C8—C9—C10	162.71 (15)	C92—C93—C94—Cl94	179.31 (16)
C8—C9—C10—C10A	38.5 (2)	C93—C94—C95—C96	0.0 (3)
C97—C9—C10—C10A	−83.17 (18)	Cl94—C94—C95—C96	−179.30 (15)
C8—C9—C10—C103	−85.97 (18)	C94—C95—C96—C91	−0.4 (3)
C97—C9—C10—C103	152.31 (15)	C92—C91—C96—C95	0.8 (3)
C7—C6A—C10A—C10B	−179.53 (16)	C97—C91—C96—C95	179.78 (18)
C6—C6A—C10A—C10B	1.0 (3)	C18A—N101—C102—O102	178.31 (17)
C7—C6A—C10A—C10	2.5 (3)	C18A—N101—C102—C103	−2.2 (3)
C6—C6A—C10A—C10	−177.06 (16)	O102—C102—C103—C104	179.14 (19)
C103—C10—C10A—C6A	98.56 (19)	N101—C102—C103—C104	−0.4 (3)
C9—C10—C10A—C6A	−26.7 (2)	O102—C102—C103—C10	−2.3 (3)
C103—C10—C10A—C10B	−79.45 (19)	N101—C102—C103—C10	178.15 (15)
C9—C10—C10A—C10B	155.26 (15)	C10A—C10—C103—C104	−55.6 (2)
N5—C4A—C10B—C1	−179.45 (16)	C9—C10—C103—C104	70.3 (2)
C4—C4A—C10B—C1	0.4 (3)	C10A—C10—C103—C102	125.93 (16)
N5—C4A—C10B—C10A	−0.5 (3)	C9—C10—C103—C102	−108.22 (17)
C4—C4A—C10B—C10A	179.36 (16)	C102—C103—C104—C14A	1.6 (3)
C2—C1—C10B—C4A	0.1 (3)	C10—C103—C104—C14A	−176.80 (16)
C2—C1—C10B—C10A	−178.72 (17)	C103—C104—C14A—C105	178.19 (19)
C6A—C10A—C10B—C4A	−0.6 (3)	C103—C104—C14A—C18A	−0.5 (3)
C10—C10A—C10B—C4A	177.37 (16)	C18A—C14A—C105—C106	0.7 (3)
C6A—C10A—C10B—C1	178.22 (17)	C104—C14A—C105—C106	−178.0 (2)
C10—C10A—C10B—C1	−3.8 (3)	C14A—C105—C106—C107	0.3 (4)
C7—C8—C87—O87	−161.00 (19)	C105—C106—C107—C108	−0.2 (4)
C9—C8—C87—O87	7.1 (3)	C106—C107—C108—C18A	−0.8 (3)
C7—C8—C87—C81	15.7 (3)	C102—N101—C18A—C108	−175.55 (17)
C9—C8—C87—C81	−176.21 (16)	C102—N101—C18A—C14A	3.3 (3)
O87—C87—C81—C86	−134.3 (2)	C107—C108—C18A—N101	−179.37 (18)
C8—C87—C81—C86	49.0 (3)	C107—C108—C18A—C14A	1.8 (3)
O87—C87—C81—C82	46.9 (3)	C105—C14A—C18A—N101	179.39 (17)
C8—C87—C81—C82	−129.76 (19)	C104—C14A—C18A—N101	−1.9 (3)
C86—C81—C82—C83	−1.6 (3)	C105—C14A—C18A—C108	−1.7 (3)
C87—C81—C82—C83	177.26 (17)	C104—C14A—C18A—C108	177.01 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N101—H101···O6^i	0.88	2.02	2.850 (2)	156
C2—H2···O102^ii	0.95	2.42	3.345 (3)	163
C108—H108···O6^i	0.95	2.57	3.291 (3)	133

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