The proton-transfer compounds of strychnine with achiral salicylic acids: strychninium 3,5-dinitro­salicylate and the strychninium 5-nitro­salicylate bis­(5-nitro­salicylic acid) adduct

In the crystal structures of the proton-transfer compounds of strychnine with 3,5-dinitro­salicylic acid, namely strychninium 3,5-dinitro­salicylate, C₂₁H₂₃N₂O₂⁺·C₇H₃N₂O₇^-, (I), and 5-nitro­salicylic acid, namely strychninium-5-nitro­salicylate-5-nitro­salicylic acid (1/1/2), C₂₁H₂₃N₂O₂⁺·C₇H₄NO₅^-·2C₇H₅NO₅, (II), protonation of one of the N atoms of the strychnine mol­ecule occurs and this group is subsequently involved in inter­molecular hydrogen-bonding inter­actions. In (I), this is four-centred, the primary being with an adjacent strychninium carbonyl O-atom acceptor in a side-to-side inter­action giving linear chains. Other inter­actions are with the phenolate and nitro O-atom acceptors of the anionic species, resulting in a one-dimensional polymer structure. In (II), the N⁺-H inter­action is three-centred, the hydrogen bonding involving carboxyl O-atom acceptors of the anion and both acid adduct species, giving unique discrete hetero-tetramer units. The structure of (II) also features [pi]-bonding inter­actions between the two acid adduct mol­ecules.

S1. Comment

Strychnine and brucine have been variously employed on a hit-or-miss basis as resolving agents for a range of chiral organic compounds, and the crystal structures of a large number of complexes with strychnine and brucine, together with their absolute configurations, have been determined. The complexes include those with acidic species, in which atom N19 of the strychnine or brucine molecule (pK_a2 = 11.7) is protonated, e.g. the N-benzoyl, N-phthaloyl and N-acetyl protected amino acids (Gould & Walkinshaw, 1984; Gould, Taylor & Walkinshaw, 1984; Gould et al., 1985; Bialońska & Ciunik, 2004a; Quinkert et al., 1986; Kuwata et al., 1993), and other chiral acid types (Gould et al., 1987; Boiadjiev et al., 1992; Wright et al., 1994; Bao et al., 1996; Costente et al., 1996; Dijksma, Gould, Parsons, Taylor & Walkinshaw, 1998; Andersson et al., 1999; Allenmark & Skogsberg, 2000; Gould et al., 2002; Bialońska et al., 2005). Other structures with neutral chiral guest species are known, e.g. with alcohols, lactones, cyanohydrins and ketones (Toda et al., 1981, 1985; Tanaka et al., 2001; Chandramohan & Ravikumar, 1999; Pinkerton et al., 1993; Yamagishi et al., 1992).

Although strychnine and brucine are both physicochemically and structurally similar and configurationally identical, brucine has proved to be the better of the two for optical resolution. This appears to be because of the presence of methoxy groups in the 2- and 3-positions of the aromatic ring, influencing the solid-state packing of the brucine molecules, which commonly form undulating parallel chain structures (Gould & Walkinshaw, 1984; Dijksma et al., 1998 Please specify unique reference; Bialońska et al., 2005). These recognize compatible molecular guest species which occupy the interstitial cavities between the chains and associate with the host through hydrogen bonding. Water or other molecules of solvation may also act, if needed, in a space-filling and/or in a proton-donor or -acceptor capacity. This is apparent in the isomorphous crystals of brucine–ethanol–water (1/1/2) (Glover et al., 1985) and brucine–propan-2-ol–water (1/1/2) (Bialońska & Ciunik, 2004b), and in brucine–acetone (1/1) structures (Bialońska & Ciunik, 2004b). Strychnine is less regular as a host structure for organic molecule recognition, often giving isolated molecular complexes or forming double-layer polymeric structures (Gould & Walkinshaw, 1984; Dijksma, Gould, Parsons, Taylor & Walkinshaw, 1998).

More recently, the structures of a number of neutral and proton-transfer compounds of strychnine and brucine with achiral organic molecules have been determined, e.g. with 4-nitrophenol (Guo et al. 2001), fumaric and maleic acids (Dijksma, Gould, Parsons & Walkinshaw, 1998), 4-hydroxybenzoic acid (Sada et al., 1998), 3-nitrobenzoic acid (Oshikawa et al., 2002), and 8-aminonaphthalene-2-sulfonic acid (Smith, Wermuth, Healy & Young, 2005). Because it was observed by Oshikawa et al. (2002) that brucine has a recognitive affinity for meta-substituted benzoic acids, we therefore considered that the analogous acids 3,5-dinitrosalicylic acid (DNSA), 5-nitrosalicylic acid (5-NSA), 5-sulfosalicylic acid (5-SSA) and 3-nitrophthalic acid (NPA) were likely candidates for similar recognition by brucine and possibly strychnine. This has proved to be the case with brucine, where good crystalline products were obtained within 1 week for DNSA, two weeks for 5-NSA and 5-SSA, and several weeks with NPA. The crystal structures of all four compounds have now been determined (Smith, Wermuth & Healy, 2005; Smith, Wermuth, Young & Healy, 2005). However, with strychnine, no complex was obtained with 5-SSA or NPA, although good crystals of the compounds with DNSA and 5-NSA were formed, albeit more slowly than with brucine. The crystal structures of these two compounds, C₂₁H₂₃N₂O₂⁺·C₇H₃N₂O₇⁻, (I), and the adduct C₂₁H₂₃N₂O₂⁺·C₇H₄NO₅⁻·2(C₇H₅NO₅), (II), respectively, are reported here.

Both compounds (I) and (II) are anhydrous, which is consistent with the structures of the proton-transfer compounds of both DNSA and 5-NSA with Lewis bases, where water or other molecules of solvation are seldom incorporated (Smith et al., 2002, 2003; Smith, Hartono et al., 2005), although the brucine complex with DNSA is a monohydrate (Smith, Wermuth & Healy, 2005). The major difference between (I) and (II) is the presence in (II) of two additional adduct molecules of 5-NSA acid, adduct formation being unusual among 5-NSA compounds, as well as among examples of brucine or strychnine complexes.

In the structures of both (I) and (II) (Figs. 1 and 2), the expected proton transfer to N19 of the strychnine molecule occurs and this group is subsequently involved in intermolecular N⁺—H···O hydrogen-bonding interactions with two O-acceptors of the anion species, and, in the case of (I), a strychnine carbonyl-O (Tables 1 and 2).

In each structure, the absolute configuration of the parent strychnine molecule (Peerdeman, 1956) is invoked. This includes the `apparent' change in configuration at C7 (R to S), which is a consequence of the change in the heirarchy of the protonated N19 group in the Cahn–Ingold–Prelog system and the introduction of a new chiral centre at N19 (S) (Smith, Wermuth, Healy & Young, 2005). This gives the overall absolute stereochemistry for the strychninium cations in (I) and (II) (as with all proton-transfer compounds of both brucine and strychnine) as C7(S), C8(S), C12(S), C13(R), C14(R), C16(S), N19(S).

In (I), the linear strychninium framework is formed through side-to-side hydrogen-bonding interactions involving the protonated N19 group and an adjacent strychnine carbonyl-O [N19–H19···O25ⁱ 3.148 (4) Å], extending along the c axis direction (Fig. 3) [for symmetry codes, see Table 1]. Atom N19 is then involved in a proximal association with both a phenolic O and a disordered nitro-O acceptor of a glide-related DNSA anion [N19···O2Dⁱⁱ 2.857 (5) and N19···O33Dⁱⁱ 3.00 (3) Å]. This generates a linear polymer structure in which, surprisingly, there are no intermolecular associations involving the O-acceptors of the DNSA carboxyl group.

In (II), an unusual discrete hetero-tetramer is formed, comprising the strychninium cation, the 5-NSA anion (molecule B) and the two 5-NSA acid adduct molecules (A and C) (Fig 4). The three-centre association with N19⁺—H involves carboxyl-O acceptors of the anion [N19···O72Bⁱ 3.223 (8) Å] and an adduct molecule A [N19···O72Aⁱⁱ 2.958 (5) Å] [for symmetry codes, see Table 2]. Completing a cyclic R₂²(6) association is the carboxyl H atom of the adduct molecule A [O71A···O72Bⁱⁱ 2.553 (6) Å]. The second adduct molecule is linearly hydrogen-bonded to the anion molecule through the carboxyl groups [2.709 (8) Å], such that both adduct molecules form π-associated stacks [ring centroid separations CgA···CgC 3.72 (1) Å (intra) and 4.09 (1) Å (inter); CgA and CgC denote the centroids of the rings in molecules A and C, respectively]. Both adduct formation and π-stacking effects are previously unknown among structures of 5-NSA compounds (Smith, Hartono et al., 2005). The tetramer units are unassociated except for an unusual side-on interaction between the intramolecularly hydrogen-bonded phenolic group of an adduct molecule C and a nitro-O of an adjacent adduct molecule A [O2C···O52A 2.854 (6) Å] (Figs. 2 and 4).

Within the DNSA anion in (I), the structural features vary slightly from those of the majority of proton-transfer compounds (Smith et al., 2003), particularly with regard to the conformation of the nitro-substituent groups. The proximal nitro group at C3 is more commonly involved in hydrogen bonding than the C5 nitro group and therefore usually shows a greater rotation out of the plane of the ring than the C5 group. In (I), this is also the case [torsion angles C2D—C3D—N3D—O33D 167.4 (5)° and C4D—C5D—N5D—O52D 179.5 (4)°]. However, the previously mentioned intermolecularly unassociated carboxyl group is noncoplanar [torsion angle C2D—C1D—C7D—O71D −166.4 (4)°], although it is involved in the intramolecular hydrogen-bond. This hydrogen bond [O2D···O72D 2.492 (5) Å] has the H atom located on the carboxyl-O, rather than on the phenolic group as is found in ca 70% of the proton-transfer compounds of DNSA (Smith et al., 2002, 2003).

With the 5-NSA species in (II), despite the presence of adduct acid molecules and the associated π-stacking effects, structural features vary little from those previously reported (Smith, Hartono et al., 2005), which includes near-coplanarity between the parent ring and both the carboxyl- and nitro-substituent groups, the invariable location of the intramolecular H atom on the phenolic O atom, and a contraction of this intramolecular O···O distance with deprotonation [2.509 (10) Å in molecule B, compared with 2.595 (5) in molecule A and 2.605 (6) Å in molecule C].

S2. Experimental

The title compounds were synthesized by heating 1 mmol quantities of strychnine (strychnidin-10-one) and either 3,5-dinitrosalicylic acid (DNSA) or 5-nitrosalicylic acid (5-NSA) in 50% ethanol–water (50 ml) for 10 min under reflux. After concentration to ca 30 ml, partial room-temperature evaporation of the hot-filtered solutions gave yellow prisms of (I) (m.p. 468–470 K) and minor colourless prisms of (II) (m.p. 487–489 K).

S3. Refinement

H atoms potentially involved in hydrogen-bonding interactions were located by difference methods but, with the exception of the strychninium atom H19 (on N19), their positional and isotropic displacement parameters were not refined. Other H atoms were included in the refinement in calculated positions [C—H(aromatic) = 0.93 Å and C—H(aliphatic) = 0.97 Å] and treated using a riding model, with U_iso(H) = 1.2U_eq(C). The atom-numbering scheme for the strychninium species in (I) and (II) (Figs. 1 and 2, respectively) follows the original Robinson convention (Holmes, 1952). Friedel pairs were averaged and the absolute configuration determined for the parent strychnine (Peerdeman, 1956) was invoked, giving the overall Cahn–Ingold–Prelog absolute stereochemistry (Eliel, 1962) as C7(S), C8(S), C12(S), C13(R), C14(R), C16(S), N19(S). One of the nitro O atoms in (I) was found to be disordered and was subsequently refined over two sites [O31D, with a site occupancy factor of 0.44 (5), and O33D, with a site occupancy factor of 0.56 (5)].

Computing details

Data collection: SMART (Bruker, 2000) for (I); CAD-4 Software (Enraf–Nonius, 1989) for (II). Cell refinement: SMART for (I); CAD-4 Software (Enraf–Nonius, 1989) for (II). Data reduction: SAINT (Bruker, 1999) for (I); XCAD4 (Harms & Wocadlo, 1995) for (II). Program(s) used to solve structure: SHELXTL (Bruker, 1997) for (I); SHELXS97 (Sheldrick, 1997) in WinGX (Farrugia, 1999) for (II). Program(s) used to refine structure: SHELXTL for (I); SHELXL97 (Sheldrick, 1997) in WinGX (Farrugia, 1999) for (II). For both compounds, molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures

	Fig. 1. The molecular configuration and atom-numbering scheme for the strychninium cation and the DNSA anion species in compound (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. Atoms O31D and O33D are disordered sites (see text).
	Fig. 2. The molecular configuration and atom-numbering scheme for the strychninium cation, the 5-NSA anion and the two 5-NSA acid adduct species in compound (II). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 3. The packing of (I) in the unit cell, viewed down the a axis. Non-interacting H atoms have been omitted. Hydrogen-bonding associations are shown as broken lines. [Symmetry codes: (iii) x, y, 1 + z; (iv) −x, −1/2 + y, −z; (v) −x, −1/2 + y, 1 − z; for others, see Table 1.]
	Fig. 4. The packing of (II) in the unit cell, viewed down the c axis. The discrete hydrogen-bonded tetrameric units are shown (dashed lines). Also illustrated are the π-bonding associations between the two 5-NSA adduct molecules (A and C). [Symmetry codes: (iii) 1 − x, −1/2 + y, 1 − z; for others, see Table 2.]

(I) strychninium 3,5-dinitrosalicylate

Crystal data

C21H23N2O2^+·C7H3N2O7^−	F(000) = 588
Mr = 562.53	Dx = 1.536 Mg m^−3
Monoclinic, P21	Melting point = 468–470 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 7.5036 (15) Å	Cell parameters from 2715 reflections
b = 17.219 (3) Å	θ = 2.4–27.3°
c = 9.4799 (19) Å	µ = 0.12 mm^−1
β = 96.905 (3)°	T = 295 K
V = 1216.0 (4) Å^3	Block, yellow
Z = 2	0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1909 reflections with F^2 > 2σ(F^2)
Radiation source: sealed tube	Rint = 0.071
Graphite monochromator	θmax = 25.0°, θmin = 2.2°
ϕ and ω scans	h = −8→8
5865 measured reflections	k = −20→18
2222 independent reflections	l = −10→11

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ^2(Fo^2) + (0.0734P)^2 + 0.1261P] where P = (Fo^2 + 2Fc^2)/3
2222 reflections	(Δ/σ)max = 0.021
384 parameters	Δρmax = 0.22 e Å^−3
1 restraint	Δρmin = −0.25 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O2D	0.5068 (5)	0.43231 (17)	0.1817 (3)	0.0558 (11)
O32D	0.4009 (7)	0.2831 (2)	0.4942 (4)	0.0913 (18)
O33D	0.500 (5)	0.2945 (5)	0.298 (2)	0.079 (7)	0.56 (5)
O51D	0.2235 (5)	0.4930 (2)	0.7604 (3)	0.0619 (11)
O52D	0.2476 (5)	0.6101 (2)	0.6866 (4)	0.0754 (14)
O71D	0.4909 (4)	0.66320 (19)	0.2467 (4)	0.0587 (11)
O72D	0.5121 (6)	0.5691 (2)	0.0964 (4)	0.0749 (14)
N3D	0.4138 (6)	0.3223 (2)	0.3908 (4)	0.0578 (14)
N5D	0.2583 (5)	0.5400 (2)	0.6715 (4)	0.0482 (12)
C1D	0.4242 (5)	0.5368 (2)	0.3194 (4)	0.0344 (12)
C2D	0.4455 (5)	0.4552 (2)	0.2928 (4)	0.0352 (12)
C3D	0.3966 (5)	0.4057 (2)	0.4013 (4)	0.0386 (12)
C4D	0.3330 (5)	0.4332 (2)	0.5222 (4)	0.0360 (12)
C5D	0.3185 (5)	0.5120 (2)	0.5413 (4)	0.0386 (12)
C6D	0.3632 (5)	0.5634 (2)	0.4403 (4)	0.0387 (11)
C7D	0.4761 (5)	0.5949 (3)	0.2183 (4)	0.0425 (12)
O31D	0.372 (6)	0.2935 (6)	0.2696 (11)	0.075 (7)	0.44 (5)
O24	0.0355 (4)	0.66153 (16)	0.2910 (3)	0.0497 (10)
O25	0.0896 (5)	0.8683 (2)	0.6125 (3)	0.0632 (13)
N9	0.1795 (4)	0.86689 (17)	0.3935 (3)	0.0339 (9)
N19	0.2533 (5)	0.82367 (19)	−0.0767 (3)	0.0420 (10)
C1	0.2695 (6)	1.0348 (2)	0.1883 (5)	0.0473 (14)
C2	0.2621 (7)	1.0958 (3)	0.2825 (5)	0.0578 (16)
C3	0.2237 (7)	1.0819 (3)	0.4178 (5)	0.0537 (16)
C4	0.1937 (5)	1.0074 (2)	0.4658 (4)	0.0406 (12)
C5	0.2039 (5)	0.9475 (2)	0.3715 (4)	0.0335 (12)
C6	0.2409 (5)	0.9602 (2)	0.2344 (4)	0.0360 (12)
C7	0.2511 (5)	0.8843 (2)	0.1561 (4)	0.0324 (11)
C8	0.1741 (5)	0.8255 (2)	0.2559 (3)	0.0300 (10)
C10	0.1016 (6)	0.8347 (2)	0.4995 (4)	0.0420 (12)
C11	0.0332 (6)	0.7531 (2)	0.4728 (4)	0.0488 (14)
C12	−0.0497 (6)	0.7328 (2)	0.3206 (4)	0.0439 (12)
C13	−0.0176 (5)	0.7986 (2)	0.2200 (4)	0.0366 (12)
C14	−0.0687 (5)	0.7863 (2)	0.0594 (4)	0.0404 (12)
C15	−0.0437 (6)	0.8661 (3)	−0.0107 (4)	0.0458 (15)
C16	0.1526 (5)	0.8839 (2)	0.0029 (4)	0.0399 (13)
C17	0.4417 (5)	0.8630 (2)	0.1308 (4)	0.0411 (12)
C18	0.4184 (6)	0.8007 (2)	0.0194 (4)	0.0414 (12)
C20	0.1387 (6)	0.7545 (2)	−0.1251 (4)	0.0474 (16)
C21	0.0438 (6)	0.7263 (2)	−0.0056 (4)	0.0444 (14)
C22	0.0561 (6)	0.6530 (3)	0.0386 (4)	0.0473 (14)
C23	−0.0316 (7)	0.6246 (3)	0.1622 (5)	0.0570 (17)
H6D	0.351800	0.616500	0.454500	0.0460*
H72D	0.51600	0.51100	0.1160	0.1000*
H4D	0.300100	0.398800	0.590200	0.0430*
H1	0.293300	1.043900	0.095600	0.0570*
H2	0.283300	1.146300	0.253900	0.0690*
H3	0.217500	1.123600	0.479300	0.0650*
H4	0.167900	0.998400	0.557900	0.0490*
H8	0.253200	0.780100	0.267900	0.0360*
H11A	−0.056500	0.743100	0.536200	0.0580*
H11B	0.132100	0.717600	0.499000	0.0580*
H12	−0.179000	0.724300	0.319100	0.0530*
H13	−0.092500	0.841800	0.245800	0.0440*
H14	−0.195300	0.771200	0.041700	0.0480*
H15A	−0.092500	0.864600	−0.110200	0.0550*
H15B	−0.106500	0.906000	0.036000	0.0550*
H16	0.168300	0.935000	−0.039500	0.0480*
H17A	0.503500	0.907600	0.097300	0.0490*
H17B	0.509500	0.843800	0.217300	0.0490*
H18A	0.521900	0.798400	−0.032700	0.0500*
H18B	0.402400	0.750400	0.062100	0.0500*
H19	0.294 (6)	0.850 (3)	−0.150 (5)	0.057 (13)*
H20A	0.051800	0.769000	−0.204800	0.0570*
H20B	0.213600	0.713400	−0.155900	0.0570*
H22	0.121900	0.618100	−0.009200	0.0570*
H23A	−0.159900	0.633700	0.143600	0.0680*
H23B	−0.012900	0.569100	0.172100	0.0680*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2D	0.091 (2)	0.0407 (17)	0.0407 (19)	0.0026 (15)	0.0278 (16)	−0.0049 (13)
O32D	0.168 (4)	0.0389 (19)	0.075 (3)	−0.006 (2)	0.048 (3)	0.0115 (19)
O33D	0.15 (2)	0.035 (4)	0.064 (8)	0.008 (6)	0.059 (11)	−0.002 (4)
O51D	0.083 (2)	0.068 (2)	0.0395 (19)	0.0042 (17)	0.0275 (17)	0.0079 (16)
O52D	0.123 (3)	0.051 (2)	0.058 (2)	0.0233 (19)	0.035 (2)	−0.0078 (17)
O71D	0.078 (2)	0.0379 (18)	0.062 (2)	−0.0036 (15)	0.0159 (17)	0.0125 (15)
O72D	0.126 (3)	0.056 (2)	0.050 (2)	−0.007 (2)	0.041 (2)	0.0069 (17)
N3D	0.101 (3)	0.0268 (19)	0.049 (2)	−0.0015 (18)	0.023 (2)	0.0021 (17)
N5D	0.058 (2)	0.049 (2)	0.040 (2)	0.0070 (17)	0.0154 (16)	−0.0012 (18)
C1D	0.037 (2)	0.038 (2)	0.030 (2)	0.0002 (16)	0.0108 (15)	0.0039 (17)
C2D	0.043 (2)	0.033 (2)	0.030 (2)	0.0014 (16)	0.0056 (17)	−0.0010 (16)
C3D	0.050 (2)	0.031 (2)	0.035 (2)	−0.0005 (17)	0.0060 (18)	−0.0021 (16)
C4D	0.044 (2)	0.037 (2)	0.028 (2)	−0.0039 (16)	0.0089 (16)	0.0058 (16)
C5D	0.042 (2)	0.042 (2)	0.033 (2)	0.0059 (17)	0.0099 (16)	0.0020 (17)
C6D	0.044 (2)	0.0293 (19)	0.044 (2)	0.0098 (17)	0.0101 (17)	0.0006 (16)
C7D	0.049 (2)	0.041 (2)	0.040 (2)	0.0034 (18)	0.0152 (18)	0.0080 (19)
O31D	0.14 (2)	0.031 (4)	0.051 (5)	−0.006 (7)	0.000 (7)	−0.011 (3)
O24	0.074 (2)	0.0345 (15)	0.0429 (17)	−0.0058 (14)	0.0161 (14)	−0.0025 (13)
O25	0.110 (3)	0.0559 (19)	0.0273 (15)	−0.0086 (18)	0.0225 (15)	−0.0061 (15)
N9	0.0499 (18)	0.0277 (16)	0.0242 (15)	−0.0061 (14)	0.0053 (13)	−0.0025 (13)
N19	0.068 (2)	0.0369 (18)	0.0240 (16)	0.0086 (16)	0.0169 (15)	0.0033 (14)
C1	0.066 (3)	0.034 (2)	0.041 (2)	−0.0002 (19)	0.003 (2)	0.0055 (19)
C2	0.084 (3)	0.031 (2)	0.056 (3)	0.007 (2)	−0.002 (2)	0.001 (2)
C3	0.074 (3)	0.039 (2)	0.045 (3)	0.015 (2)	−0.005 (2)	−0.014 (2)
C4	0.044 (2)	0.040 (2)	0.037 (2)	0.0066 (18)	0.0022 (17)	−0.0041 (18)
C5	0.037 (2)	0.034 (2)	0.029 (2)	0.0065 (16)	0.0024 (15)	−0.0009 (16)
C6	0.044 (2)	0.032 (2)	0.031 (2)	0.0031 (16)	0.0005 (16)	−0.0006 (16)
C7	0.040 (2)	0.0316 (19)	0.0261 (18)	0.0012 (15)	0.0064 (15)	0.0043 (15)
C8	0.046 (2)	0.0258 (17)	0.0196 (17)	0.0060 (16)	0.0093 (15)	0.0004 (14)
C10	0.057 (2)	0.047 (2)	0.023 (2)	0.001 (2)	0.0084 (17)	−0.0014 (17)
C11	0.075 (3)	0.037 (2)	0.037 (2)	−0.007 (2)	0.018 (2)	0.0059 (17)
C12	0.047 (2)	0.047 (2)	0.040 (2)	−0.0075 (18)	0.0147 (18)	−0.0041 (19)
C13	0.039 (2)	0.040 (2)	0.032 (2)	0.0023 (16)	0.0098 (16)	−0.0064 (16)
C14	0.040 (2)	0.046 (2)	0.034 (2)	−0.0002 (18)	−0.0006 (17)	−0.0029 (18)
C15	0.056 (3)	0.053 (3)	0.0255 (19)	0.013 (2)	−0.0075 (17)	−0.0010 (18)
C16	0.063 (3)	0.035 (2)	0.0224 (18)	0.0115 (18)	0.0078 (17)	0.0032 (16)
C17	0.050 (2)	0.039 (2)	0.036 (2)	−0.0022 (18)	0.0117 (17)	0.0044 (17)
C18	0.053 (2)	0.038 (2)	0.035 (2)	0.0105 (18)	0.0125 (18)	0.0025 (17)
C20	0.066 (3)	0.048 (3)	0.028 (2)	0.007 (2)	0.0051 (19)	−0.0030 (18)
C21	0.050 (3)	0.050 (2)	0.032 (2)	0.0002 (19)	−0.0002 (17)	−0.0137 (19)
C22	0.063 (3)	0.039 (2)	0.040 (2)	−0.0068 (19)	0.006 (2)	−0.0160 (19)
C23	0.074 (3)	0.043 (3)	0.056 (3)	−0.022 (2)	0.016 (2)	−0.011 (2)

Geometric parameters (Å, º)

O2D—C2D	1.262 (5)	C7—C16	1.548 (5)
O31D—N3D	1.256 (13)	C7—C17	1.523 (5)
O32D—N3D	1.204 (5)	C7—C8	1.544 (5)
O33D—N3D	1.25 (3)	C8—C13	1.511 (5)
O51D—N5D	1.219 (5)	C10—C11	1.507 (5)
O52D—N5D	1.219 (5)	C11—C12	1.541 (5)
O71D—C7D	1.209 (6)	C12—C13	1.519 (5)
O72D—C7D	1.296 (6)	C13—C14	1.539 (5)
O72D—H72D	1.02	C14—C21	1.512 (5)
O24—C23	1.415 (6)	C14—C15	1.548 (6)
O24—C12	1.427 (5)	C15—C16	1.495 (6)
O25—C10	1.230 (5)	C17—C18	1.501 (5)
N3D—C3D	1.446 (5)	C20—C21	1.490 (6)
N5D—C5D	1.447 (5)	C21—C22	1.330 (6)
N9—C10	1.342 (5)	C22—C23	1.493 (6)
N9—C8	1.483 (4)	C1—H1	0.9308
N9—C5	1.419 (5)	C2—H2	0.9302
N19—C18	1.500 (5)	C3—H3	0.9296
N19—C16	1.534 (5)	C4—H4	0.9298
N19—C20	1.508 (5)	C8—H8	0.9799
N19—H19	0.91 (5)	C11—H11A	0.9701
C1D—C6D	1.363 (5)	C11—H11B	0.9704
C1D—C2D	1.440 (5)	C12—H12	0.9796
C1D—C7D	1.470 (6)	C13—H13	0.9808
C2D—C3D	1.418 (5)	C14—H14	0.9797
C3D—C4D	1.377 (5)	C15—H15A	0.9703
C4D—C5D	1.375 (5)	C15—H15B	0.9697
C5D—C6D	1.375 (5)	C16—H16	0.9803
C4D—H4D	0.9304	C17—H17A	0.9701
C6D—H6D	0.9296	C17—H17B	0.9697
C1—C6	1.382 (5)	C18—H18A	0.9700
C1—C2	1.384 (6)	C18—H18B	0.9696
C2—C3	1.369 (7)	C20—H20A	0.9695
C3—C4	1.389 (6)	C20—H20B	0.9703
C4—C5	1.373 (5)	C22—H22	0.9295
C5—C6	1.379 (5)	C23—H23A	0.9704
C6—C7	1.509 (5)	C23—H23B	0.9688
C7D—O72D—H72D	100	C13—C14—C15	105.9 (3)
C12—O24—C23	115.8 (3)	C13—C14—C21	114.4 (3)
O32D—N3D—C3D	119.0 (4)	C14—C15—C16	108.3 (3)
O31D—N3D—O32D	119.2 (8)	N19—C16—C7	104.9 (3)
O31D—N3D—C3D	116.1 (7)	N19—C16—C15	110.9 (3)
O32D—N3D—O33D	117.3 (7)	C7—C16—C15	115.9 (3)
O33D—N3D—C3D	119.2 (7)	C7—C17—C18	104.5 (3)
O51D—N5D—C5D	118.9 (3)	N19—C18—C17	104.9 (3)
O51D—N5D—O52D	123.6 (4)	N19—C20—C21	109.5 (3)
O52D—N5D—C5D	117.5 (4)	C14—C21—C22	122.8 (4)
C5—N9—C8	109.3 (3)	C14—C21—C20	115.4 (3)
C8—N9—C10	119.5 (3)	C20—C21—C22	121.8 (4)
C5—N9—C10	126.1 (3)	C21—C22—C23	122.5 (4)
C16—N19—C18	107.4 (3)	O24—C23—C22	112.7 (4)
C16—N19—C20	112.8 (3)	C2—C1—H1	120.56
C18—N19—C20	112.1 (3)	C6—C1—H1	120.65
C20—N19—H19	113 (3)	C1—C2—H2	119.99
C16—N19—H19	106 (3)	C3—C2—H2	119.94
C18—N19—H19	105 (3)	C2—C3—H3	118.98
C2D—C1D—C6D	122.0 (3)	C4—C3—H3	119.06
C2D—C1D—C7D	120.4 (3)	C3—C4—H4	121.47
C6D—C1D—C7D	117.5 (3)	C5—C4—H4	121.36
O2D—C2D—C1D	120.7 (3)	N9—C8—H8	109.22
O2D—C2D—C3D	124.7 (3)	C7—C8—H8	109.16
C1D—C2D—C3D	114.6 (3)	C13—C8—H8	109.19
N3D—C3D—C2D	120.9 (3)	C10—C11—H11A	108.01
N3D—C3D—C4D	116.2 (3)	C10—C11—H11B	108.05
C2D—C3D—C4D	122.9 (3)	C12—C11—H11A	107.92
C3D—C4D—C5D	119.3 (3)	C12—C11—H11B	107.87
C4D—C5D—C6D	120.9 (3)	H11A—C11—H11B	107.21
N5D—C5D—C6D	120.5 (3)	O24—C12—H12	109.57
N5D—C5D—C4D	118.6 (3)	C11—C12—H12	109.58
C1D—C6D—C5D	120.3 (3)	C13—C12—H12	109.51
O72D—C7D—C1D	116.6 (4)	C8—C13—H13	105.66
O71D—C7D—C1D	122.8 (4)	C12—C13—H13	105.68
O71D—C7D—O72D	120.6 (4)	C14—C13—H13	105.60
C3D—C4D—H4D	120.33	C13—C14—H14	109.09
C5D—C4D—H4D	120.35	C15—C14—H14	109.10
C1D—C6D—H6D	119.88	C21—C14—H14	109.05
C5D—C6D—H6D	119.87	C14—C15—H15A	110.05
C2—C1—C6	118.8 (4)	C14—C15—H15B	110.02
C1—C2—C3	120.1 (5)	C16—C15—H15A	110.00
C2—C3—C4	122.0 (4)	C16—C15—H15B	110.08
C3—C4—C5	117.2 (4)	H15A—C15—H15B	108.38
N9—C5—C4	128.4 (3)	N19—C16—H16	108.33
N9—C5—C6	109.8 (3)	C7—C16—H16	108.25
C4—C5—C6	121.9 (3)	C15—C16—H16	108.33
C5—C6—C7	110.7 (3)	C7—C17—H17A	110.84
C1—C6—C5	120.1 (3)	C7—C17—H17B	110.86
C1—C6—C7	129.1 (4)	C18—C17—H17A	110.81
C6—C7—C8	102.8 (3)	C18—C17—H17B	110.87
C6—C7—C16	114.7 (3)	H17A—C17—H17B	108.90
C6—C7—C17	113.0 (3)	N19—C18—H18A	110.79
C16—C7—C17	101.7 (3)	N19—C18—H18B	110.76
C8—C7—C17	111.5 (3)	C17—C18—H18A	110.78
C8—C7—C16	113.6 (3)	C17—C18—H18B	110.77
C7—C8—C13	118.6 (3)	H18A—C18—H18B	108.85
N9—C8—C13	105.7 (3)	N19—C20—H20A	109.83
N9—C8—C7	104.5 (3)	N19—C20—H20B	109.75
O25—C10—N9	122.8 (3)	C21—C20—H20A	109.77
O25—C10—C11	121.7 (4)	C21—C20—H20B	109.76
N9—C10—C11	115.4 (3)	H20A—C20—H20B	108.24
C10—C11—C12	117.4 (3)	C21—C22—H22	118.74
C11—C12—C13	110.0 (3)	C23—C22—H22	118.73
O24—C12—C11	103.8 (3)	O24—C23—H23A	109.07
O24—C12—C13	114.2 (3)	O24—C23—H23B	109.11
C8—C13—C12	107.8 (3)	C22—C23—H23A	109.01
C8—C13—C14	112.5 (3)	C22—C23—H23B	109.06
C12—C13—C14	118.6 (3)	H23A—C23—H23B	107.81
C15—C14—C21	109.2 (3)
C23—O24—C12—C13	−67.2 (5)	C3—C4—C5—N9	179.9 (4)
C12—O24—C23—C22	86.9 (5)	C4—C5—C6—C7	177.8 (3)
C23—O24—C12—C11	173.0 (3)	N9—C5—C6—C1	179.9 (4)
O33D—N3D—C3D—C4D	−167.1 (17)	N9—C5—C6—C7	−2.5 (4)
O32D—N3D—C3D—C4D	−11.8 (6)	C4—C5—C6—C1	0.2 (6)
O33D—N3D—C3D—C2D	12.1 (17)	C1—C6—C7—C16	−46.9 (6)
O32D—N3D—C3D—C2D	167.4 (5)	C5—C6—C7—C16	135.7 (3)
O52D—N5D—C5D—C6D	0.7 (6)	C1—C6—C7—C17	69.0 (5)
O52D—N5D—C5D—C4D	179.5 (4)	C5—C6—C7—C8	11.9 (4)
O51D—N5D—C5D—C4D	0.5 (6)	C5—C6—C7—C17	−108.4 (4)
O51D—N5D—C5D—C6D	−178.4 (4)	C1—C6—C7—C8	−170.7 (4)
C10—N9—C5—C6	−163.2 (4)	C17—C7—C8—C13	−137.5 (3)
C8—N9—C5—C6	−8.7 (4)	C17—C7—C8—N9	105.2 (3)
C5—N9—C10—O25	−22.4 (6)	C16—C7—C8—C13	−23.3 (4)
C8—N9—C5—C4	170.9 (4)	C6—C7—C16—N19	152.3 (3)
C8—N9—C10—O25	−174.5 (4)	C16—C7—C17—C18	−40.9 (3)
C5—N9—C10—C11	159.2 (4)	C8—C7—C17—C18	80.4 (3)
C10—N9—C8—C13	46.2 (4)	C8—C7—C16—N19	−89.9 (3)
C10—N9—C5—C4	16.5 (6)	C6—C7—C17—C18	−164.4 (3)
C8—N9—C10—C11	7.0 (5)	C6—C7—C8—N9	−16.1 (4)
C5—N9—C8—C13	−110.2 (3)	C17—C7—C16—N19	30.0 (3)
C5—N9—C8—C7	15.8 (4)	C6—C7—C8—C13	101.2 (3)
C10—N9—C8—C7	172.2 (3)	C16—C7—C8—N9	−140.7 (3)
C18—N19—C16—C15	−134.5 (3)	C6—C7—C16—C15	−85.1 (4)
C20—N19—C16—C7	115.2 (3)	C17—C7—C16—C15	152.7 (3)
C20—N19—C18—C17	−141.0 (3)	C8—C7—C16—C15	32.8 (5)
C18—N19—C20—C21	74.2 (4)	C7—C8—C13—C12	171.5 (3)
C16—N19—C20—C21	−47.1 (4)	N9—C8—C13—C12	−71.8 (3)
C16—N19—C18—C17	−16.6 (4)	C7—C8—C13—C14	38.8 (4)
C18—N19—C16—C7	−8.7 (4)	N9—C8—C13—C14	155.6 (3)
C20—N19—C16—C15	−10.5 (4)	N9—C10—C11—C12	−36.8 (5)
C7D—C1D—C2D—O2D	−0.9 (6)	O25—C10—C11—C12	144.7 (4)
C6D—C1D—C2D—C3D	0.5 (5)	C10—C11—C12—O24	131.7 (4)
C6D—C1D—C2D—O2D	−178.1 (4)	C10—C11—C12—C13	9.1 (5)
C6D—C1D—C7D—O72D	−171.6 (4)	O24—C12—C13—C8	−73.0 (4)
C2D—C1D—C7D—O71D	−166.6 (4)	O24—C12—C13—C14	56.3 (5)
C7D—C1D—C2D—C3D	177.7 (3)	C11—C12—C13—C8	43.3 (4)
C2D—C1D—C6D—C5D	−0.5 (6)	C11—C12—C13—C14	172.5 (3)
C2D—C1D—C7D—O72D	11.1 (6)	C8—C13—C14—C15	−60.2 (4)
C6D—C1D—C7D—O71D	10.7 (6)	C12—C13—C14—C15	172.7 (3)
C7D—C1D—C6D—C5D	−177.7 (3)	C8—C13—C14—C21	60.1 (4)
O2D—C2D—C3D—N3D	−0.3 (6)	C12—C13—C14—C21	−67.0 (4)
C1D—C2D—C3D—N3D	−178.9 (4)	C13—C14—C21—C20	−122.8 (4)
C1D—C2D—C3D—C4D	0.3 (5)	C15—C14—C21—C20	−4.3 (5)
O2D—C2D—C3D—C4D	178.9 (4)	C21—C14—C15—C16	−54.5 (4)
C2D—C3D—C4D—C5D	−1.2 (6)	C15—C14—C21—C22	176.6 (4)
N3D—C3D—C4D—C5D	178.0 (4)	C13—C14—C21—C22	58.2 (5)
C3D—C4D—C5D—N5D	−177.5 (4)	C13—C14—C15—C16	69.1 (4)
C3D—C4D—C5D—C6D	1.3 (6)	C14—C15—C16—C7	−56.9 (4)
C4D—C5D—C6D—C1D	−0.5 (6)	C14—C15—C16—N19	62.5 (4)
N5D—C5D—C6D—C1D	178.3 (4)	C7—C17—C18—N19	36.2 (4)
C6—C1—C2—C3	−1.2 (7)	N19—C20—C21—C14	55.6 (5)
C2—C1—C6—C7	−176.5 (4)	N19—C20—C21—C22	−125.3 (4)
C2—C1—C6—C5	0.7 (7)	C20—C21—C22—C23	177.3 (4)
C1—C2—C3—C4	0.9 (8)	C14—C21—C22—C23	−3.7 (7)
C2—C3—C4—C5	−0.1 (7)	C21—C22—C23—O24	−62.6 (6)
C3—C4—C5—C6	−0.5 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O72D—H72D···O2D	1.02	1.50	2.492 (5)	165
N19—H19···O25^i	0.91 (5)	2.59 (5)	3.148 (4)	120 (4)
N19—H19···O2D^ii	0.91 (5)	2.11 (5)	2.857 (5)	139 (4)
N19—H19···O33D^ii	0.91 (5)	2.41 (6)	3.00 (3)	123 (4)
C1—H1···O72D^ii	0.93	2.50	3.374 (6)	156
C4—H4···O25	0.93	2.3884	2.923 (5)	116
C18—H18A···O33D^ii	0.97	2.50	3.14 (2)	124
C18—H18B···O71D	0.97	2.34	3.204 (5)	148
C20—H20A···O25^i	0.97	2.47	3.153 (5)	127
C20—H20B···O52D^i	0.97	2.36	3.223 (5)	148

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

(II) strychninium–5-nitrosalicylate–5-nitrosalicylic acid (1/1/2)

Crystal data

C21H23N2O2^+·C7H4NO5^−·2C7H5NO5	F(000) = 920
Mr = 883.77	Dx = 1.513 Mg m^−3
Monoclinic, P21	Melting point = 486.5–488.8 K
Hall symbol: P 2yb	Cu Kα radiation, λ = 1.54180 Å
a = 7.5762 (9) Å	Cell parameters from 25 reflections
b = 12.3729 (9) Å	θ = 20–30°
c = 20.891 (4) Å	µ = 1.01 mm^−1
β = 97.96 (1)°	T = 295 K
V = 1939.5 (5) Å^3	Prismatic, colourless
Z = 2	0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4F diffractometer	Rint = 0.045
Radiation source: sealed tube	θmax = 69.9°, θmin = 2.1°
Graphite monochromator	h = −9→9
ω/2θ scans	k = 0→15
3960 measured reflections	l = 0→25
3856 independent reflections	3 standard reflections every 160 min
3427 reflections with F^2 > 2σ(F^2)	intensity decay: 0.0%

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.168	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.1204P)^2 + 0.567P] where P = (Fo^2 + 2Fc^2)/3
3856 reflections	(Δ/σ)max = 0.002
585 parameters	Δρmax = 0.57 e Å^−3
1 restraint	Δρmin = −0.35 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

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

	x	y	z	Uiso*/Ueq
O24	0.7869 (4)	0.5600 (3)	0.08916 (16)	0.0490 (10)
O25	0.2797 (5)	0.6610 (4)	−0.04851 (16)	0.0706 (13)
N9	0.3564 (4)	0.7165 (3)	0.05539 (14)	0.0436 (10)
N19	0.6401 (4)	0.8093 (4)	0.25759 (16)	0.0388 (9)
C1	0.2057 (6)	0.9603 (4)	0.1252 (3)	0.0519 (16)
C2	0.0712 (7)	0.9977 (5)	0.0786 (3)	0.0632 (18)
C3	0.0240 (6)	0.9399 (5)	0.0217 (3)	0.0620 (18)
C4	0.1092 (5)	0.8445 (5)	0.0098 (2)	0.0536 (16)
C5	0.2465 (5)	0.8086 (4)	0.05664 (18)	0.0401 (11)
C6	0.2926 (5)	0.8652 (4)	0.11367 (19)	0.0384 (11)
C7	0.4309 (5)	0.8028 (3)	0.15808 (17)	0.0353 (10)
C8	0.4982 (5)	0.7200 (3)	0.11164 (16)	0.0329 (10)
C10	0.3895 (6)	0.6616 (4)	0.00053 (19)	0.0462 (11)
C11	0.5604 (7)	0.6039 (5)	0.0042 (2)	0.0558 (16)
C12	0.7242 (6)	0.6478 (4)	0.04896 (19)	0.0419 (11)
C13	0.6725 (5)	0.7475 (3)	0.08614 (17)	0.0341 (10)
C14	0.8109 (5)	0.7957 (3)	0.13871 (18)	0.0360 (10)
C15	0.7329 (5)	0.9017 (4)	0.1603 (2)	0.0406 (11)
C16	0.5768 (5)	0.8739 (4)	0.19561 (19)	0.0395 (11)
C17	0.3504 (5)	0.7478 (4)	0.21320 (18)	0.0421 (13)
C18	0.5101 (6)	0.7180 (4)	0.26145 (18)	0.0474 (13)
C20	0.8295 (5)	0.7699 (5)	0.2614 (2)	0.0499 (14)
C21	0.8589 (5)	0.7226 (4)	0.19722 (19)	0.0406 (13)
C22	0.9266 (5)	0.6252 (4)	0.1929 (2)	0.0478 (14)
C23	0.9539 (6)	0.5760 (4)	0.1291 (3)	0.0546 (16)
O2A	0.4440 (6)	0.1873 (3)	0.52283 (18)	0.0671 (13)
O51A	0.3213 (9)	0.4584 (5)	0.27038 (18)	0.106 (2)
O52A	0.2491 (7)	0.5766 (4)	0.33510 (19)	0.0779 (16)
O71A	0.2467 (6)	0.4909 (3)	0.56211 (16)	0.0624 (13)
O72A	0.3384 (6)	0.3297 (3)	0.60045 (15)	0.0623 (13)
N5A	0.2999 (7)	0.4865 (4)	0.3241 (2)	0.0648 (16)
C1A	0.3432 (6)	0.3664 (4)	0.4887 (2)	0.0423 (12)
C2A	0.4095 (6)	0.2628 (4)	0.4772 (2)	0.0478 (12)
C3A	0.4401 (8)	0.2358 (4)	0.4150 (3)	0.0587 (16)
C4A	0.4026 (8)	0.3089 (5)	0.3656 (2)	0.0588 (16)
C5A	0.3371 (6)	0.4104 (4)	0.3774 (2)	0.0466 (12)
C6A	0.3098 (6)	0.4407 (4)	0.4391 (2)	0.0440 (12)
C7A	0.3099 (6)	0.3934 (4)	0.5553 (2)	0.0465 (12)
O2B	0.9661 (9)	0.1656 (6)	0.2680 (3)	0.113 (3)
O51B	0.3799 (9)	0.4163 (8)	0.0944 (5)	0.172 (4)
O52B	0.2223 (8)	0.2917 (8)	0.1271 (4)	0.132 (3)
O71B	0.4728 (11)	0.0520 (4)	0.2997 (2)	0.111 (3)
O72B	0.7682 (12)	0.0401 (5)	0.3201 (2)	0.107 (2)
N5B	0.3668 (8)	0.3367 (6)	0.1263 (3)	0.090 (2)
C1B	0.6505 (10)	0.1674 (5)	0.2431 (3)	0.069 (2)
C2B	0.8184 (10)	0.2067 (5)	0.2348 (3)	0.076 (2)
C3B	0.8385 (10)	0.2929 (6)	0.1918 (3)	0.078 (2)
C4B	0.6885 (8)	0.3349 (5)	0.1571 (3)	0.0679 (19)
C5B	0.5252 (9)	0.2929 (5)	0.1648 (3)	0.0649 (19)
C6B	0.5033 (11)	0.2105 (5)	0.2068 (3)	0.070 (2)
C7B	0.6235 (14)	0.0794 (5)	0.2920 (3)	0.083 (3)
O2C	0.0777 (6)	0.6857 (3)	0.4299 (2)	0.0784 (16)
O51C	0.1326 (10)	0.9609 (6)	0.6799 (3)	0.120 (3)
O52C	0.2815 (6)	1.0635 (4)	0.6255 (2)	0.0771 (16)
O71C	0.3032 (8)	0.9862 (4)	0.3988 (2)	0.0865 (16)
O72C	0.2100 (7)	0.8272 (4)	0.35736 (19)	0.0827 (18)
N5C	0.1956 (7)	0.9817 (4)	0.6314 (2)	0.0668 (16)
C1C	0.1801 (7)	0.8626 (4)	0.4665 (2)	0.0536 (16)
C2C	0.1061 (7)	0.7608 (5)	0.4767 (3)	0.0584 (16)
C3C	0.0586 (7)	0.7347 (5)	0.5369 (3)	0.0658 (19)
C4C	0.0857 (7)	0.8070 (5)	0.5874 (3)	0.0634 (17)
C5C	0.1621 (6)	0.9066 (4)	0.5772 (3)	0.0533 (14)
C6C	0.2088 (6)	0.9357 (4)	0.5188 (2)	0.0523 (14)
C7C	0.2281 (9)	0.8906 (5)	0.4028 (2)	0.0667 (18)
H1	0.236800	0.998300	0.163500	0.0620*
H2	0.012300	1.061700	0.085400	0.0760*
H3	−0.066600	0.965800	−0.009000	0.0750*
H4	0.076200	0.805500	−0.028000	0.0650*
H8	0.508800	0.648800	0.132400	0.0390*
H11A	0.591800	0.600400	−0.039200	0.0670*
H11B	0.540600	0.530300	0.017500	0.0670*
H12	0.816300	0.668400	0.022600	0.0500*
H13	0.643600	0.804600	0.053900	0.0410*
H14	0.919500	0.811800	0.119900	0.0430*
H15A	0.822700	0.941100	0.188700	0.0490*
H15B	0.693100	0.946600	0.123000	0.0490*
H16	0.516000	0.940000	0.205000	0.0670*
H17A	0.272500	0.796900	0.232200	0.0500*
H17B	0.283300	0.684000	0.197800	0.0500*
H18A	0.477700	0.712200	0.304600	0.0570*
H18B	0.560600	0.649700	0.250100	0.0570*
H19	0.629 (5)	0.857 (6)	0.295 (7)	0.066 (9)*
H20A	0.911100	0.829500	0.272400	0.0600*
H20B	0.852500	0.715400	0.294900	0.0600*
H22	0.958400	0.585500	0.230500	0.0570*
H23A	1.028300	0.623300	0.107200	0.0660*
H23B	1.014700	0.507200	0.136500	0.0660*
H2A	0.407000	0.237000	0.550000	0.0800*
H3A	0.486000	0.168300	0.406900	0.0700*
H4A	0.421300	0.290200	0.324000	0.0710*
H6A	0.269600	0.509900	0.447000	0.0530*
H71A	0.241000	0.508000	0.604000	0.0730*
H2B	0.914000	0.120000	0.287000	0.1320*
H3B	0.950600	0.320000	0.187400	0.0940*
H4B	0.696900	0.391500	0.128400	0.0810*
H6B	0.390100	0.184300	0.210500	0.0840*
H71C	0.359000	1.00800	0.366000	0.1020*
H2C	0.123000	0.735000	0.405000	0.0960*
H3C	0.008100	0.667700	0.543100	0.0790*
H4C	0.053500	0.789600	0.627500	0.0760*
H6C	0.259100	1.003100	0.513500	0.0630*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O24	0.0546 (17)	0.0406 (16)	0.0526 (17)	−0.0002 (14)	0.0107 (14)	−0.0007 (14)
O25	0.068 (2)	0.102 (3)	0.0378 (16)	−0.015 (2)	−0.0073 (15)	−0.0142 (19)
N9	0.0387 (16)	0.064 (2)	0.0278 (15)	−0.0079 (16)	0.0031 (12)	−0.0058 (16)
N19	0.0377 (15)	0.0507 (19)	0.0274 (14)	−0.0090 (15)	0.0023 (12)	0.0007 (14)
C1	0.039 (2)	0.052 (3)	0.067 (3)	−0.0017 (19)	0.016 (2)	0.007 (2)
C2	0.048 (2)	0.058 (3)	0.087 (4)	0.007 (2)	0.021 (2)	0.034 (3)
C3	0.040 (2)	0.084 (4)	0.062 (3)	0.004 (2)	0.007 (2)	0.038 (3)
C4	0.0385 (19)	0.083 (4)	0.038 (2)	−0.007 (2)	0.0007 (16)	0.026 (2)
C5	0.0338 (17)	0.053 (2)	0.0343 (18)	−0.0052 (17)	0.0075 (14)	0.0122 (17)
C6	0.0342 (18)	0.044 (2)	0.0376 (19)	−0.0042 (16)	0.0066 (14)	0.0097 (16)
C7	0.0345 (17)	0.043 (2)	0.0284 (16)	−0.0020 (16)	0.0045 (14)	0.0007 (16)
C8	0.0347 (17)	0.0392 (19)	0.0240 (15)	−0.0065 (15)	0.0014 (13)	−0.0001 (15)
C10	0.055 (2)	0.052 (2)	0.0312 (18)	−0.017 (2)	0.0042 (17)	−0.0055 (18)
C11	0.064 (3)	0.060 (3)	0.042 (2)	−0.004 (2)	0.002 (2)	−0.019 (2)
C12	0.047 (2)	0.043 (2)	0.0375 (19)	−0.0061 (18)	0.0125 (17)	−0.0034 (17)
C13	0.0350 (17)	0.039 (2)	0.0293 (16)	−0.0049 (15)	0.0078 (14)	0.0040 (15)
C14	0.0349 (16)	0.039 (2)	0.0349 (18)	−0.0062 (16)	0.0074 (14)	0.0028 (16)
C15	0.0393 (19)	0.043 (2)	0.040 (2)	−0.0100 (17)	0.0070 (15)	−0.0051 (18)
C16	0.0399 (19)	0.043 (2)	0.0359 (19)	−0.0041 (17)	0.0062 (15)	−0.0061 (17)
C17	0.0346 (18)	0.062 (3)	0.0309 (17)	−0.0083 (18)	0.0093 (14)	0.0032 (18)
C18	0.047 (2)	0.068 (3)	0.0277 (17)	−0.012 (2)	0.0065 (15)	0.0058 (19)
C20	0.040 (2)	0.074 (3)	0.0337 (19)	−0.010 (2)	−0.0018 (16)	−0.001 (2)
C21	0.0292 (17)	0.057 (3)	0.0348 (19)	−0.0076 (17)	0.0018 (14)	0.0030 (18)
C22	0.0367 (19)	0.062 (3)	0.044 (2)	0.0015 (19)	0.0030 (16)	0.013 (2)
C23	0.043 (2)	0.055 (3)	0.066 (3)	0.006 (2)	0.008 (2)	0.003 (2)
O2A	0.100 (3)	0.0450 (18)	0.057 (2)	0.0137 (19)	0.0129 (19)	0.0092 (16)
O51A	0.185 (5)	0.100 (4)	0.038 (2)	0.031 (4)	0.029 (3)	0.006 (2)
O52A	0.113 (3)	0.065 (3)	0.057 (2)	0.013 (2)	0.016 (2)	0.017 (2)
O71A	0.097 (3)	0.0479 (19)	0.0424 (17)	0.0127 (19)	0.0105 (17)	−0.0010 (14)
O72A	0.102 (3)	0.0483 (19)	0.0353 (15)	0.0023 (19)	0.0052 (16)	0.0020 (14)
N5A	0.082 (3)	0.064 (3)	0.050 (2)	−0.007 (2)	0.015 (2)	0.006 (2)
C1A	0.046 (2)	0.041 (2)	0.039 (2)	−0.0072 (18)	0.0023 (16)	−0.0033 (17)
C2A	0.057 (2)	0.043 (2)	0.043 (2)	−0.003 (2)	0.0058 (18)	−0.0002 (19)
C3A	0.081 (3)	0.041 (2)	0.057 (3)	0.002 (2)	0.020 (2)	−0.007 (2)
C4A	0.079 (3)	0.058 (3)	0.043 (2)	−0.008 (3)	0.021 (2)	−0.009 (2)
C5A	0.052 (2)	0.050 (2)	0.038 (2)	−0.005 (2)	0.0070 (17)	−0.0002 (19)
C6A	0.049 (2)	0.041 (2)	0.041 (2)	−0.0032 (18)	0.0024 (17)	−0.0034 (17)
C7A	0.059 (2)	0.043 (2)	0.036 (2)	−0.006 (2)	0.0017 (17)	−0.0048 (18)
O2B	0.119 (4)	0.114 (5)	0.105 (4)	0.027 (4)	0.015 (3)	0.035 (4)
O51B	0.106 (4)	0.193 (9)	0.204 (8)	−0.026 (5)	−0.023 (5)	0.145 (8)
O52B	0.083 (3)	0.172 (7)	0.140 (5)	−0.038 (4)	0.011 (3)	0.035 (5)
O71B	0.206 (7)	0.074 (3)	0.061 (3)	0.023 (4)	0.046 (4)	0.019 (3)
O72B	0.202 (6)	0.071 (3)	0.061 (3)	−0.042 (4)	0.062 (3)	−0.005 (2)
N5B	0.072 (3)	0.115 (5)	0.082 (4)	−0.017 (3)	0.012 (3)	0.024 (4)
C1B	0.120 (5)	0.043 (3)	0.050 (3)	−0.011 (3)	0.031 (3)	−0.006 (2)
C2B	0.110 (5)	0.066 (4)	0.049 (3)	0.032 (4)	0.003 (3)	0.003 (3)
C3B	0.090 (4)	0.077 (4)	0.070 (4)	0.005 (4)	0.019 (3)	0.016 (3)
C4B	0.083 (4)	0.061 (3)	0.060 (3)	−0.005 (3)	0.011 (3)	0.020 (3)
C5B	0.090 (4)	0.056 (3)	0.052 (3)	−0.011 (3)	0.022 (3)	0.003 (2)
C6B	0.123 (5)	0.050 (3)	0.042 (2)	−0.023 (3)	0.025 (3)	−0.004 (2)
C7B	0.155 (7)	0.055 (3)	0.044 (3)	0.005 (4)	0.030 (4)	−0.012 (3)
O2C	0.083 (3)	0.058 (2)	0.088 (3)	−0.006 (2)	−0.010 (2)	−0.027 (2)
O51C	0.181 (6)	0.103 (4)	0.091 (4)	−0.020 (4)	0.067 (4)	−0.030 (3)
O52C	0.098 (3)	0.070 (3)	0.061 (2)	−0.011 (2)	0.003 (2)	−0.021 (2)
O71C	0.151 (4)	0.057 (2)	0.051 (2)	−0.013 (3)	0.012 (2)	−0.0043 (19)
O72C	0.121 (4)	0.072 (3)	0.050 (2)	0.000 (3)	−0.006 (2)	−0.019 (2)
N5C	0.081 (3)	0.067 (3)	0.054 (2)	0.010 (3)	0.015 (2)	−0.012 (2)
C1C	0.059 (3)	0.043 (2)	0.054 (3)	0.006 (2)	−0.009 (2)	−0.007 (2)
C2C	0.049 (2)	0.054 (3)	0.069 (3)	0.003 (2)	−0.003 (2)	−0.013 (2)
C3C	0.052 (3)	0.049 (3)	0.097 (4)	0.001 (2)	0.012 (3)	−0.005 (3)
C4C	0.058 (3)	0.061 (3)	0.074 (3)	0.007 (3)	0.019 (2)	−0.001 (3)
C5C	0.048 (2)	0.049 (2)	0.062 (3)	0.008 (2)	0.004 (2)	−0.007 (2)
C6C	0.055 (2)	0.046 (2)	0.052 (3)	0.007 (2)	−0.006 (2)	−0.006 (2)
C7C	0.093 (4)	0.057 (3)	0.043 (2)	0.009 (3)	−0.016 (2)	−0.007 (2)

Geometric parameters (Å, º)

O24—C12	1.414 (6)	C22—C23	1.505 (7)
O24—C23	1.430 (6)	C1—H1	0.9298
O25—C10	1.227 (5)	C2—H2	0.9295
O2A—C2A	1.334 (6)	C3—H3	0.9291
O51A—N5A	1.207 (6)	C4—H4	0.9297
O52A—N5A	1.212 (7)	C8—H8	0.9803
O71A—C7A	1.313 (6)	C11—H11B	0.9698
O72A—C7A	1.225 (6)	C11—H11A	0.9697
O2A—H2A	0.9072	C12—H12	0.9806
O71A—H71A	0.9072	C13—H13	0.9797
O2B—C2B	1.333 (10)	C14—H14	0.9801
O51B—N5B	1.201 (12)	C15—H15B	0.9704
O52B—N5B	1.230 (10)	C15—H15A	0.9699
O71B—C7B	1.223 (13)	C16—H16	0.9719
O72B—C7B	1.267 (12)	C17—H17A	0.9694
O2B—H2B	0.8216	C17—H17B	0.9694
O2C—C2C	1.344 (7)	C18—H18B	0.9705
O51C—N5C	1.206 (8)	C18—H18A	0.9692
O52C—N5C	1.219 (7)	C20—H20B	0.9701
O71C—C7C	1.320 (8)	C20—H20A	0.9693
O71C—H71C	0.900	C22—H22	0.9295
O72C—C7C	1.224 (7)	C23—H23B	0.9700
O2C—H2C	0.8999	C23—H23A	0.9700
N9—C5	1.414 (6)	C1A—C6A	1.382 (6)
N9—C10	1.385 (5)	C1A—C7A	1.486 (6)
N9—C8	1.479 (5)	C1A—C2A	1.409 (7)
N19—C16	1.541 (6)	C2A—C3A	1.392 (7)
N19—C20	1.507 (5)	C3A—C4A	1.372 (8)
N19—C18	1.508 (6)	C4A—C5A	1.385 (8)
N19—H19	0.99 (13)	C5A—C6A	1.385 (6)
N5A—C5A	1.456 (6)	C3A—H3A	0.9292
N5B—C5B	1.454 (9)	C4A—H4A	0.9290
N5C—C5C	1.460 (7)	C6A—H6A	0.9311
C1—C2	1.388 (8)	C1B—C7B	1.526 (9)
C1—C6	1.386 (7)	C1B—C6B	1.367 (10)
C2—C3	1.391 (9)	C1B—C2B	1.395 (11)
C3—C4	1.384 (8)	C2B—C3B	1.416 (9)
C4—C5	1.398 (6)	C3B—C4B	1.363 (10)
C5—C6	1.384 (6)	C4B—C5B	1.372 (9)
C6—C7	1.512 (6)	C5B—C6B	1.370 (9)
C7—C8	1.545 (5)	C3B—H3B	0.9294
C7—C17	1.535 (5)	C4B—H4B	0.9298
C7—C16	1.540 (6)	C6B—H6B	0.9300
C8—C13	1.529 (5)	C1C—C6C	1.412 (6)
C10—C11	1.471 (7)	C1C—C7C	1.469 (6)
C11—C12	1.545 (7)	C1C—C2C	1.407 (8)
C12—C13	1.537 (6)	C2C—C3C	1.393 (9)
C13—C14	1.530 (5)	C3C—C4C	1.377 (9)
C14—C15	1.532 (6)	C4C—C5C	1.390 (8)
C14—C21	1.524 (6)	C5C—C6C	1.365 (7)
C15—C16	1.517 (6)	C3C—H3C	0.9296
C17—C18	1.509 (6)	C4C—H4C	0.9297
C20—C21	1.507 (6)	C6C—H6C	0.9298
C21—C22	1.318 (7)
C12—O24—C23	115.9 (4)	C14—C15—H15A	110.12
C2A—O2A—H2A	85.73	C16—C15—H15A	110.15
C7A—O71A—H71A	112.68	C16—C15—H15B	110.10
C2B—O2B—H2B	95.08	H15A—C15—H15B	108.49
C7C—O71C—H71C	125	C14—C15—H15B	110.08
C2C—O2C—H2C	85.21	C7—C16—H16	104.87
C8—N9—C10	118.5 (3)	C15—C16—H16	109.30
C5—N9—C8	109.1 (3)	N19—C16—H16	111.59
C5—N9—C10	125.8 (3)	C18—C17—H17B	110.96
C18—N19—C20	112.3 (4)	C7—C17—H17B	110.90
C16—N19—C18	107.7 (3)	H17A—C17—H17B	108.98
C16—N19—C20	113.3 (3)	C7—C17—H17A	110.92
C18—N19—H19	106 (4)	C18—C17—H17A	110.90
C16—N19—H19	108 (6)	C17—C18—H18B	110.87
C20—N19—H19	110 (4)	N19—C18—H18B	110.90
O51A—N5A—C5A	119.2 (5)	C17—C18—H18A	110.88
O52A—N5A—C5A	118.9 (4)	H18A—C18—H18B	108.78
O51A—N5A—O52A	121.9 (5)	N19—C18—H18A	110.89
O52B—N5B—C5B	119.5 (7)	C21—C20—H20A	109.77
O51B—N5B—C5B	119.2 (6)	C21—C20—H20B	109.75
O51B—N5B—O52B	121.4 (8)	N19—C20—H20A	109.74
O51C—N5C—C5C	118.0 (6)	N19—C20—H20B	109.73
O52C—N5C—C5C	119.2 (4)	H20A—C20—H20B	108.23
O51C—N5C—O52C	122.8 (5)	C23—C22—H22	118.90
C2—C1—C6	118.8 (5)	C21—C22—H22	118.90
C1—C2—C3	120.3 (5)	O24—C23—H23B	109.50
C2—C3—C4	121.4 (5)	C22—C23—H23B	109.52
C3—C4—C5	117.7 (5)	O24—C23—H23A	109.47
N9—C5—C4	128.8 (4)	C22—C23—H23A	109.49
C4—C5—C6	121.1 (4)	H23A—C23—H23B	108.09
N9—C5—C6	110.2 (3)	C2A—C1A—C7A	118.3 (4)
C1—C6—C7	129.2 (4)	C6A—C1A—C7A	121.0 (4)
C5—C6—C7	109.9 (4)	C2A—C1A—C6A	120.6 (4)
C1—C6—C5	120.7 (4)	C1A—C2A—C3A	119.1 (4)
C16—C7—C17	101.7 (3)	O2A—C2A—C1A	123.6 (4)
C6—C7—C17	111.9 (3)	O2A—C2A—C3A	117.2 (4)
C8—C7—C17	112.2 (3)	C2A—C3A—C4A	120.0 (5)
C8—C7—C16	115.0 (3)	C3A—C4A—C5A	120.4 (4)
C6—C7—C16	114.1 (3)	N5A—C5A—C6A	119.9 (4)
C6—C7—C8	102.4 (3)	N5A—C5A—C4A	119.1 (4)
C7—C8—C13	116.6 (3)	C4A—C5A—C6A	121.0 (4)
N9—C8—C13	107.3 (3)	C1A—C6A—C5A	118.8 (4)
N9—C8—C7	104.6 (3)	O72A—C7A—C1A	122.8 (4)
O25—C10—C11	122.0 (4)	O71A—C7A—O72A	122.4 (4)
O25—C10—N9	121.0 (4)	O71A—C7A—C1A	114.8 (4)
N9—C10—C11	117.0 (4)	C4A—C3A—H3A	119.95
C10—C11—C12	119.2 (4)	C2A—C3A—H3A	120.04
C11—C12—C13	110.4 (4)	C5A—C4A—H4A	119.81
O24—C12—C13	113.9 (3)	C3A—C4A—H4A	119.80
O24—C12—C11	105.4 (4)	C5A—C6A—H6A	120.56
C8—C13—C12	106.9 (3)	C1A—C6A—H6A	120.61
C8—C13—C14	112.1 (3)	C6B—C1B—C7B	118.4 (7)
C12—C13—C14	118.6 (3)	C2B—C1B—C7B	122.8 (7)
C13—C14—C15	106.9 (3)	C2B—C1B—C6B	118.9 (6)
C13—C14—C21	114.1 (3)	C1B—C2B—C3B	121.4 (6)
C15—C14—C21	109.3 (3)	O2B—C2B—C1B	121.1 (6)
C14—C15—C16	107.9 (4)	O2B—C2B—C3B	117.5 (7)
C7—C16—C15	115.8 (3)	C2B—C3B—C4B	118.0 (7)
N19—C16—C15	110.7 (3)	C3B—C4B—C5B	119.5 (6)
N19—C16—C7	104.4 (3)	N5B—C5B—C6B	117.9 (6)
C7—C17—C18	104.1 (3)	C4B—C5B—C6B	123.2 (6)
N19—C18—C17	104.5 (4)	N5B—C5B—C4B	118.9 (6)
N19—C20—C21	109.6 (3)	C1B—C6B—C5B	118.9 (7)
C14—C21—C20	115.8 (4)	O71B—C7B—C1B	120.0 (7)
C14—C21—C22	122.7 (4)	O71B—C7B—O72B	126.6 (7)
C20—C21—C22	121.5 (4)	O72B—C7B—C1B	113.4 (8)
C21—C22—C23	122.2 (4)	C2B—C3B—H3B	120.96
O24—C23—C22	110.7 (4)	C4B—C3B—H3B	121.05
C6—C1—H1	120.60	C5B—C4B—H4B	120.29
C2—C1—H1	120.60	C3B—C4B—H4B	120.23
C1—C2—H2	119.89	C1B—C6B—H6B	120.58
C3—C2—H2	119.78	C5B—C6B—H6B	120.49
C4—C3—H3	119.24	C2C—C1C—C7C	120.2 (5)
C2—C3—H3	119.37	C6C—C1C—C7C	121.3 (5)
C3—C4—H4	121.19	C2C—C1C—C6C	118.6 (4)
C5—C4—H4	121.07	O2C—C2C—C1C	122.4 (5)
C7—C8—H8	109.39	O2C—C2C—C3C	117.4 (5)
C13—C8—H8	109.41	C1C—C2C—C3C	120.2 (5)
N9—C8—H8	109.34	C2C—C3C—C4C	120.8 (6)
H11A—C11—H11B	107.08	C3C—C4C—C5C	118.7 (6)
C12—C11—H11B	107.45	N5C—C5C—C6C	119.1 (4)
C10—C11—H11B	107.50	C4C—C5C—C6C	122.4 (5)
C10—C11—H11A	107.52	N5C—C5C—C4C	118.5 (5)
C12—C11—H11A	107.52	C1C—C6C—C5C	119.4 (5)
C11—C12—H12	109.01	O71C—C7C—C1C	115.6 (4)
O24—C12—H12	109.06	O72C—C7C—C1C	122.4 (6)
C13—C12—H12	109.03	O71C—C7C—O72C	121.9 (5)
C12—C13—H13	106.24	C2C—C3C—H3C	119.69
C14—C13—H13	106.14	C4C—C3C—H3C	119.56
C8—C13—H13	106.16	C3C—C4C—H4C	120.67
C21—C14—H14	108.78	C5C—C4C—H4C	120.67
C13—C14—H14	108.74	C1C—C6C—H6C	120.27
C15—C14—H14	108.88	C5C—C6C—H6C	120.28
C23—O24—C12—C13	−67.4 (5)	C10—C11—C12—O24	126.0 (4)
C23—O24—C12—C11	171.5 (4)	O24—C12—C13—C14	55.0 (5)
C12—O24—C23—C22	88.9 (5)	C11—C12—C13—C14	173.3 (3)
C10—N9—C5—C6	−158.0 (4)	C11—C12—C13—C8	45.5 (4)
C8—N9—C10—C11	4.3 (6)	O24—C12—C13—C8	−72.7 (4)
C8—N9—C5—C6	−7.3 (4)	C8—C13—C14—C21	58.4 (4)
C10—N9—C8—C13	45.8 (5)	C12—C13—C14—C21	−66.8 (4)
C10—N9—C5—C4	21.7 (7)	C12—C13—C14—C15	172.2 (3)
C10—N9—C8—C7	170.2 (4)	C8—C13—C14—C15	−62.6 (4)
C5—N9—C10—C11	152.5 (4)	C15—C14—C21—C22	179.0 (4)
C5—N9—C8—C13	−107.4 (3)	C13—C14—C15—C16	68.6 (4)
C8—N9—C5—C4	172.4 (4)	C15—C14—C21—C20	−2.8 (5)
C5—N9—C10—O25	−28.0 (7)	C13—C14—C21—C20	−122.5 (4)
C5—N9—C8—C7	17.0 (4)	C13—C14—C21—C22	59.4 (5)
C8—N9—C10—O25	−176.3 (4)	C21—C14—C15—C16	−55.3 (4)
C18—N19—C20—C21	77.3 (5)	C14—C15—C16—C7	−54.8 (5)
C16—N19—C18—C17	−14.8 (4)	C14—C15—C16—N19	63.8 (4)
C20—N19—C16—C15	−11.8 (6)	C7—C17—C18—N19	35.6 (4)
C18—N19—C16—C15	−136.6 (4)	N19—C20—C21—C14	53.9 (5)
C20—N19—C16—C7	113.5 (4)	N19—C20—C21—C22	−127.9 (5)
C18—N19—C16—C7	−11.3 (4)	C20—C21—C22—C23	178.9 (4)
C16—N19—C20—C21	−45.0 (6)	C14—C21—C22—C23	−3.0 (6)
C20—N19—C18—C17	−140.2 (3)	C21—C22—C23—O24	−64.3 (6)
O51A—N5A—C5A—C4A	2.4 (8)	C6A—C1A—C2A—O2A	−179.8 (5)
O52A—N5A—C5A—C6A	1.7 (8)	C7A—C1A—C6A—C5A	−177.8 (4)
O51A—N5A—C5A—C6A	−178.7 (6)	C2A—C1A—C7A—O71A	−179.4 (4)
O52A—N5A—C5A—C4A	−177.2 (5)	C6A—C1A—C7A—O71A	0.5 (7)
O51B—N5B—C5B—C4B	−8.5 (11)	C7A—C1A—C2A—C3A	179.5 (5)
O51B—N5B—C5B—C6B	172.0 (8)	C7A—C1A—C2A—O2A	0.1 (7)
O52B—N5B—C5B—C4B	171.5 (7)	C2A—C1A—C6A—C5A	2.1 (7)
O52B—N5B—C5B—C6B	−7.9 (10)	C6A—C1A—C2A—C3A	−0.4 (7)
O51C—N5C—C5C—C4C	−10.5 (8)	C6A—C1A—C7A—O72A	−179.8 (5)
O52C—N5C—C5C—C4C	171.3 (5)	C2A—C1A—C7A—O72A	0.3 (7)
O51C—N5C—C5C—C6C	170.4 (6)	O2A—C2A—C3A—C4A	178.2 (5)
O52C—N5C—C5C—C6C	−7.8 (7)	C1A—C2A—C3A—C4A	−1.2 (8)
C6—C1—C2—C3	0.6 (8)	C2A—C3A—C4A—C5A	1.1 (9)
C2—C1—C6—C7	−174.3 (5)	C3A—C4A—C5A—C6A	0.7 (8)
C2—C1—C6—C5	0.2 (7)	C3A—C4A—C5A—N5A	179.5 (5)
C1—C2—C3—C4	−0.2 (8)	C4A—C5A—C6A—C1A	−2.2 (7)
C2—C3—C4—C5	−0.8 (8)	N5A—C5A—C6A—C1A	178.9 (4)
C3—C4—C5—N9	−178.1 (4)	C7B—C1B—C2B—C3B	−176.2 (6)
C3—C4—C5—C6	1.6 (7)	C6B—C1B—C2B—O2B	−178.5 (6)
C4—C5—C6—C1	−1.3 (7)	C6B—C1B—C2B—C3B	2.7 (9)
C4—C5—C6—C7	174.2 (4)	C7B—C1B—C2B—O2B	2.7 (10)
N9—C5—C6—C1	178.4 (4)	C6B—C1B—C7B—O72B	175.7 (6)
N9—C5—C6—C7	−6.1 (5)	C2B—C1B—C7B—O72B	−5.4 (9)
C5—C6—C7—C16	140.9 (4)	C7B—C1B—C6B—C5B	177.1 (6)
C1—C6—C7—C16	−44.2 (6)	C2B—C1B—C7B—O71B	176.1 (6)
C5—C6—C7—C17	−104.3 (4)	C2B—C1B—C6B—C5B	−1.8 (9)
C1—C6—C7—C8	−169.0 (4)	C6B—C1B—C7B—O71B	−2.8 (9)
C1—C6—C7—C17	70.7 (6)	O2B—C2B—C3B—C4B	179.4 (6)
C5—C6—C7—C8	16.0 (4)	C1B—C2B—C3B—C4B	−1.8 (10)
C16—C7—C17—C18	−42.3 (4)	C2B—C3B—C4B—C5B	0.0 (10)
C17—C7—C16—N19	32.3 (4)	C3B—C4B—C5B—C6B	0.9 (10)
C6—C7—C8—C13	98.9 (4)	C3B—C4B—C5B—N5B	−178.5 (6)
C8—C7—C16—C15	32.8 (5)	N5B—C5B—C6B—C1B	179.4 (6)
C6—C7—C8—N9	−19.3 (4)	C4B—C5B—C6B—C1B	0.0 (10)
C6—C7—C16—C15	−85.0 (4)	C2C—C1C—C6C—C5C	−0.9 (7)
C16—C7—C8—C13	−25.4 (4)	C2C—C1C—C7C—O72C	−1.7 (9)
C8—C7—C16—N19	−89.1 (4)	C7C—C1C—C6C—C5C	179.9 (7)
C8—C7—C17—C18	81.1 (4)	C2C—C1C—C7C—O71C	−177.4 (5)
C6—C7—C17—C18	−164.5 (4)	C7C—C1C—C2C—O2C	0.5 (8)
C6—C7—C16—N19	153.0 (3)	C7C—C1C—C2C—C3C	−179.2 (5)
C17—C7—C16—C15	154.3 (4)	C6C—C1C—C2C—O2C	−178.7 (5)
C17—C7—C8—C13	−141.0 (3)	C6C—C1C—C2C—C3C	1.6 (8)
C16—C7—C8—N9	−143.6 (3)	C6C—C1C—C7C—O72C	177.5 (6)
C17—C7—C8—N9	100.8 (3)	C6C—C1C—C7C—O71C	1.8 (8)
N9—C8—C13—C14	157.9 (3)	C1C—C2C—C3C—C4C	−1.0 (8)
C7—C8—C13—C12	172.6 (3)	O2C—C2C—C3C—C4C	179.2 (5)
N9—C8—C13—C12	−70.6 (4)	C2C—C3C—C4C—C5C	−0.2 (8)
C7—C8—C13—C14	41.2 (4)	C3C—C4C—C5C—N5C	−178.2 (5)
O25—C10—C11—C12	150.4 (5)	C3C—C4C—C5C—C6C	0.9 (8)
N9—C10—C11—C12	−30.1 (6)	N5C—C5C—C6C—C1C	178.7 (5)
C10—C11—C12—C13	2.7 (6)	C4C—C5C—C6C—C1C	−0.3 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N19—H19···O72B^i	0.99 (13)	2.52 (7)	3.233 (8)	128 (2)
N19—H19···O72A^ii	0.99 (13)	2.19 (13)	2.958 (5)	133 (2)
O71A—H71A···O72B^ii	0.91	1.65	2.553 (6)	179
O71C—H71C···O71B^i	0.90	1.81	2.709 (8)	179
O2A—H2A···O72A	0.91	1.69	2.595 (5)	180
O2B—H2B···O72B	0.82	1.70	2.509 (10)	168
O2C—H2C···O72C	0.90	1.71	2.605 (6)	179
C2—H2···O25^iii	0.93	2.55	3.329 (7)	141
C3B—H3B···O52B^iv	0.93	2.58	3.372 (10)	143
C4—H4···O25	0.93	2.44	2.957 (7)	115
C4B—H4B···O24	0.93	2.37	3.259 (7)	159
C11—H11B···O51B	0.97	2.57	3.394 (11)	143
C16—H16···O71B^i	0.97	2.47	3.268 (7)	139
C18—H18A···O52A	0.97	2.55	3.191 (7)	123
C22—H22···O51C^v	0.93	2.59	3.424 (8)	149

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