Cocrystals of 6-propyl-2-thio­uracil: N-H...O versus N-H...S hydrogen bonds

In order to investigate the relative stability of N-H...O and N-H...S hydrogen bonds, we cocrystallized the anti­thyroid drug 6-propyl-2-thio­uracil with two complementary heterocycles. In the cocrystal pyrimidin-2-amine-6-propyl-2-thio­uracil (1/2), C₄H₅N₃·2C₇H₁₀N₂OS, (I), the `base pair' is connected by one N-H...S and one N-H...N hydrogen bond. Homodimers of 6-propyl-2-thio­uracil linked by two N-H...S hydrogen bonds are observed in the cocrystal N-(6-acetamido­pyridin-2-yl)acetamide-6-propyl-2-thio­uracil (1/2), C₉H₁₁N₃O₂·2C₇H₁₀N₂OS, (II). The crystal structure of 6-propyl-2-thio­uracil itself, C₇H₁₀N₂OS, (III), is stabilized by pairwise N-H...O and N-H...S hydrogen bonds. In all three structures, N-H...S hydrogen bonds occur only within R₂²(8) patterns, whereas N-H...O hydrogen bonds tend to connect the homo- and heterodimers into extended networks. In agreement with related structures, the hydrogen-bonding capability of C=O and C=S groups seems to be comparable.

S1. Comment

Hydrogen-bond interactions with an S atom as an acceptor are important in biological processes. For example, sulfur-containing nucleosides are components of the anticodon of transfer RNAs. They exhibit the same arrangement of hydrogen-donor and -acceptor groups as unmodified nucleosides, but the replacement of an O with an S atom induces changes in their properties and interactions. The thio residue can be selectively photoactivated, so that it is used as an intrinsic photolabel to probe the nucleic acid structure and to identify interactions within nucleic acids or between nucleic acids and proteins (Favre et al., 1998). Furthermore, the enhanced base-pairing specificity of thionucleosides can be utilized, for example, in the design of antisense oligonucleotides (Testa et al., 1999).

Because of its reduced electronegativity, an S atom should be a weaker hydrogen-bond acceptor than an O atom. Many theoretical and experimental investigations have been concerned with the stability of the N—H···O and the N—H···S hydrogen bond, but there is no clear tendency. Ab initio energy calculations (Šponer et al., 1997; Basilio Janke et al., 2001) and a study of the thermodynamics of RNA duplexes containing thiouridine (Testa et al., 1999) showed that a base pair connected by an N—H···O bond is more stable than that with an N—H···S hydrogen bond. In the case of 2-thiouridine, the Watson–Crick base pair with adenine is preferred over the wobble base pair with guanine, while 4-thiouridine increases the stability of the wobble base pair compared with the Watson–Crick base pairing. In contrast, the infrared spectroscopic red shift of the N—H stretching frequency indicated that the N—H···S is comparable or even stronger than the N—H···O interaction (Lautié & Novak, 1980; Biswal & Wategaonkar, 2009).

In order to study the stability of the N—H···S hydrogen bond in the presence of a competitive carbonyl O atom as an acceptor, we cocrystallized 2-aminopyrimidine and N-(6-acetamidopyridin-2-yl)acetamide, respectively, with the antithyroid drug 6-propyl-2-thiouracil, also known as propylthiouracil. It inhibits the synthesis of thyroid hormones and has been used for the treatment of hyperthyroidism caused by Graves' disease (Cooper, 2005). Because of its risk of serious liver injury, 6-propyl-2-thiouracil is used as a second-line drug for patients who are intolerant of other therapies (Bahn et al., 2009).

We chose 2-aminopyrimidine because of its adjacent amine and imine groups resembling the donor–acceptor site of adenine. Since it has a mirror plane bisecting the molecule along the C—NH₂ bond, one 2-aminopyrimidine molecule may be hydrogen bonded to two 6-propyl-2-thiouracil molecules. Indeed the asymmetric unit of cocrystal (I), namely 2-aminopyrimidine–6-propyl-2-thiouracil (1/2), contains two 6-propyl-2-thiouracil molecules and one 2-aminopyrimidine molecule (Fig. 1). The 2-aminopyrimidine molecule forms dihedral angles of 17.1 (1) and 10.6 (1)° with the thiouracil rings of molecules A and B, respectively. Different propyl side-chain conformations are observed: in molecule A, the methyl C atom C9A and the thiouracil ring atom C6A are synclinal with the C8A—C9A bond almost perpendicular to the ring, while in molecule B they are antiperiplanar with a dihedral angle of 32.7 (2)° between the thiouracil ring and the plane through the side chain (Table 1). Each 6-propyl-2-thiouracil molecule is hydrogen-bonded to the 2-aminopyrimidine molecule by an R₂²(8) motif (Bernstein et al., 1995) characterized by one N—H···S and one N—H···N bond. The O atoms participate in N—H···O interactions (Table 2) connecting the 6-propyl-2-thiouracil molecules to chains running along the b axis. The packing of (I) shows layers parallel to (101) containing circular arrangements of four adjacent trimeric units with an R₈⁸(34) hydrogen-bond pattern (Fig. 2).

Its participation in the `base pairing' of (I) suggests that the S atom is an acceptor competitive with the O atom. Hence, we were also interested in whether both S and O atoms can be hydrogen bonded simultaneously to a complementary molecule. Since 6-propyl-2-thiouracil possesses an acceptor–donor–acceptor site, we cocrystallized it with N-(6-acetamidopyridin-2-yl)acetamide, which exhibits a donor–acceptor–donor site.

Cocrystal (II), namely N-(6-acetamidopyridin-2-yl)acetamide–6-propyl-2-thiouracil (1/2), contains three symmetry-independent complexes, each consisting of two 6-propyl-2-thiouracil molecules and one N-(6-acetamidopyridin-2-yl)acetamide molecule (Fig. 3). The molecular structures of the six propylthiouracil and the three N-(6-acetamidopyridin-2-yl)acetamide molecules, respectively, are very similar. The r.m.s deviation for all non-H atoms of the 6-propyl-2-thiouracil molecules varies from 0.012 to 0.028 Å, confirming its planarity. All side chains show an extended conformation with C8 antiperiplanar to N1 and C9 antiperiplanar to C6 (Table 6). Both N—H bonds of the N-(6-acetamidopyridin-2-yl)acetamide molecules are directed to the same side as the pyridine N atom, while the methyl groups are antiperiplanar to the ring atoms C2 and C6 (Table 7). Thus a dihedral angle of 12.5 (1) to 15.6 (1)° is formed between the planes through one of the amide groups and the pyridine ring (Table 8). The hydrogen-bond patterns within the three complexes are also identical. The 6-propyl-2-thiouracil molecules are linked to dimers by an R₂²(8) motif with two N—H···S bonds. In addition, an N—H···O bond connects one 6-propyl-2-thiouracil to N-(6-acetamidopyridin-2-yl)acetamide. However, the geometric arrangements of the complexes show some flexibility. The planes through the two 6-propyl-2-thiouracil molecules of a dimer enclose a dihedral angle ranging from 4.4 (1) to 11.9 (1)°, while dihedral angles of 2.0 (1) to 9.7 (1)° are observed between the planes through the pyridine ring and the neighbouring 6-propyl-2-thiouracil molecule (Table 9). In the packing, all three complexes are twisted by 17° with respect to each other and are connected by N—H···O bonds to chains running along [310] (Fig. 4). Furthermore, a second chain is formed consisting of N—H···O-bonded symmetry-related complexes aligned along the b axis. Altogether, an extended three-dimensional network of hydrogen bonds is observed (Table 3).

In spite of the appropriate arrangement of donor and acceptor groups, 6-propyl-2-thiouracil does not form three hydrogen bonds to N-(6-acetamidopyridin-2-yl)acetamide in (II), but undergoes homodimerization without participation of the carbonyl O atom. In order to further investigate its preferred hydrogen-bonding interactions, we analysed related crystal structures. Two structures containing 6-propyl-2-thiouracil are present in the Cambridge Structural Database (CSD, Version 5.32 of November 2010, plus two updates; Allen, 2002), namely a 1,4-dioxane solvate [refcode BUWYOH (Okabe et al., 1983)] and a charge-transfer complex with diiodine [refcode HAFLAC (Antoniadis et al., 2003)]. The latter structure is not further considered, since the S atom is connected to the diiodine molecule and hence can hardly participate as a hydrogen-bond acceptor. In the 1,4-dioxane solvate, only the carbonyl O atom takes part in the hydrogen bonding and connects the 6-propyl-2-thiouracil molecules to chains, while no N—H···S interactions are observed. In the solvent-free structure of the selenium analogue of 6-propyl-2-thiouracil [refcode PELHEU (Antoniadis et al., 2006)], the molecules are hydrogen bonded to chains by R₂²(8) interactions involving either N—H···Se or N—H···O bonds. We therefore undertook crystallization experiments with 6-propyl-2-thiouracil alone to study whether similar interactions can be observed.

The crystal structure of 6-propyl-2-thiouracil, (III), is isostructural with PELHEU (Fig. 5). The thiouracil rings of the two independent molecules are planar [r.m.s deviations = 0.006 (A) and 0.016 Å (B) for all non-H atoms] and the propyl side chains are again extended but slightly twisted with the planes through the ring and the side chain enclosing dihedral angles of 26.0 (2)° in A and 29.8 (2)° in B (Table 4). The 6-propyl-2-thiouracil molecules are connected to chains running along the b axis by two kinds of hydrogen-bond interactions (Table 5). Although both show the same R₂²(8) graph set, the hydrogen-bond pattern consists of either two N—H···O or two N—H···S interactions (Fig. 6). In the crystal packing, two adjacent chains are stabilized by van der Waals interactions forming tubes (Fig. 7).

In (I)–(III), 6-propyl-2-thiouracil exhibits different side-chain conformations. The dihedral angle between the planar thiouracil ring and the plane through the side chain varies from 2.0 (2) to 89.4 (1)°, although an extended arrangement is preferred. Since sufficient donor groups are available both O and S atoms participate in the hydrogen bonding. The N—H···O bonds have different functions: they connect hydrogen-bonded 6-propyl-2-thiouracil molecules either with itself [in (I)] or with the other cocrystal component [in (II)] thus forming chains, or they stabilize homodimers of 6-propyl-2-thiouracil with an R₂²(8) pattern [in (III)]. In contrast, the S atoms are only involved in R₂²(8) hydrogen-bond formation linking the 6-propyl-2-thiouracil molecules to a heterodimer [in (I)] or to a homodimer [in (II) and (III)].

From the hydrogen-bond interactions in the three structures [(I)–(III)], it is not evident whether an N—H···O or an N—H···S bond is stronger. A CSD search of six-membered ring compounds with hydrogen-bonding sites similar to 2-thiouracil yielded four different types of R₂²(8) patterns. Nineteen entries showed R₂²(8) motifs characterized by two N—H···O bonds; the S atoms take part as acceptors only in five of them [refcodes LACJIJ (Tashkhodzhaev et al., 2002), XUHJIY (Pawlowski et al., 2009), XEXWAZ, XEXWED and XEXWIH (Balalaie et al., 2006)], whereby chains stabilized by N—H···S bonds are observed only in XUHJIY. Nine structures contain two different R₂²(8) patterns with either two N—H···O or two N—H···S bonds [refcodes CASPUI (Hu et al., 2005), CUKBOA (Hori et al., 2009), GEMCAC (Read et al., 1988), PABPAL (Chierotti et al., 2010), RAPNAY (Long et al., 2005), TURCIL01 (Tiekink, 1989), TURCIL02 (Munshi & Guru Row, 2006), WIVJAM (Coxall et al., 2000) and ZEWDOU (Ferrari et al., 1995)]. Furthermore, six entries showed R₂²(8) interactions consisting of two N—H···S bonds [refcodes FALWOF (Orzeszko et al., 2004), JESWEK (Xue et al., 2006), MTURAC (Hawkinson, 1975), PABNIR (Chierotti et al., 2010), VOKBUT (Luo et al., 2008) and ZUWMUZ (Branch et al., 1996)]. In three of these structures, the O atoms do not participate in hydrogen bonds. Finally, R₂²(8) motifs with one N—H···O and one N—H···S bond are only observed in EAZTHY (Voutsas et al., 1978).

The CSD study might suggest that an N—H···O is more stable than an N—H···S bond, but some structures revealed hydrogen-bond interactions only with C═ S as a supposedly weaker acceptor group. Although the R₂²(8) motif with two N—H···O bonds is more abundant in the CSD, it is not formed in two of our three structures. A closer examination of the hydrogen-bonding interactions between 6-propyl-2-thiouracil and 2-aminopyrimidine in (I) revealed unusually large N···S distances [N21···S2A = 3.6234 (18) Å and N21···S2B = 3.5145 (17) Å]. Assumedly the complex is further stabilized by a weak C—H···O interaction, which leads to a slightly twisted arrangement of the molecules. The hydrogen-bond pattern with the O atom as an acceptor appears to be essential for the packing in (I). If the N—H···O bond was instead present in the R₂²(8) motif (an interaction similar to the 2-thiouracil–adenine Watson–Crick base pair), the heterodimer between 6-propyl-2-thiouracil and 2-aminopyrimidine would be further stabilized by a C—H···S instead of a C—H···O bond and the 6-propyl-2-thiouracil chains linked by N—H···S instead of N—H···O bonds. The C—H···S bond and chains connected by N—H···S bonds seem to be less stable, since they are rarely observed in crystal structures (Domagała et al., 2003; Pawlowski et al., 2009).

The hydrogen-bond interactions in (II) can be rationalized by similar arguments. If the homodimer of 6-propyl-2-thiouracil was linked by an R₂²(8) motif with two N—H···O bonds, the N—H···S bonds would connect the 6-propyl-2-thiouracil and N-(6-acetamidopyridin-2-yl)acetamide molecules to chains. The desired heterodimer with three hydrogen bonds is not observed. This is probably caused by the fact that the intramolecular distances between the hydrogen donor and acceptor groups of 6-propyl-2-thiouracil do not match with those of N-(6-acetamidopyridin-2-yl)acetamide (pyrimidine–thio N···S ca 2.6 Å and pyridine–amide N···N ca 2.3 Å). Therefore, formation of the desired complex may result in a strained arrangement; no such cocrystal has yet been reported in the CSD. The hydrogen-bonding interactions in (III) are similar to those of its selenium analogue and to the nine entries of the CSD study (see above). In none of the three structures, (I)–(III), an R₂²(8) motif with one N—H···O and one N—H···S bond is observed.

Obviously, the relative strength of the N—H···O and N—H···S bonds cannot be clearly judged, since there are many factors affecting hydrogen-bond formation in the crystal. All donor groups will strive to form hydrogen bonds with available acceptor groups within a favourable crystal packing. This complex situation might explain why previous theoretical and experimental studies revealed different relative stabilities for the N—H···O and N—H···S hydrogen bonds. As a result of our investigation, C═O and C═ S are indeed competitive acceptor groups.

Related literature

For related literature, see: Allen (2002); Antoniadis et al. (2003, 2006); Bahn et al. (2009); Balalaie et al. (2006); Basilio Janke, Dunger, Limbach & Weisz (2001); Biswal & Wategaonkar (2009); Branch et al. (1996); Chierotti et al. (2010); Cooper (2005); Coxall et al. (2000); Domagała et al. (2003); Favre et al. (1998); Ferrari et al. (1995); Hawkinson (1975); Hori et al. (2009); Hu et al. (2005); Lautié & Novak (1980); Le Page (1987, 1988); Long et al. (2005); Luo et al. (2008); Munshi & Guru Row (2006); Okabe et al. (1983); Orzeszko et al. (2004); Pawlowski et al. (2009); Read et al. (1988); Sheldrick (2008); Spek (2009); Tashkhodzhaev et al. (2002); Testa et al. (1999); Tiekink (1989); Voutsas et al. (1978); Xue et al. (2006); Šponer et al. (1997).

S2. Experimental

Crystals of (III) were obtained by solvent evaporation from 6-propyl-2-thiouracil (4.7 mg, 0.028 mmol) dissolved in dimethyl sulfoxide (40 µl). Cocrystallization attempts with 6-propyl-2-thiouracil (3.3 mg, 0.019 mmol) and 2-aminopyrimidine (4.3 mg, 0.045 mmol) from n-propanol (350 µl) yielded (I). Single crystals of (II) were obtained during attempts to cocrystallize 6-propyl-2-thiouracil (2.5 mg, 0.015 mmol) and N-(6-acetamidopyridin-2-yl)acetamide (2.6 mg; 0.015 mmol) from dimethylacetamide (90 µl). All experiments were performed at room temperature using commercially available compounds.

S3. Refinement

All H atoms were initially located by difference Fourier synthesis. Subsequently, H atoms bonded to C atoms were refined using a riding model, with methyl C—H = 0.98 Å, secondary C—H = 0.99 Å and aromatic C—H = 0.95 Å, and with U_iso(H) = 1.5U_eq(C) for methyl or 1.2U_eq(C) for secondary and aromatic H atoms. In (II) and (III), H atoms bonded to N atoms were refined using a riding model, with amide N—H = 0.88 Å and U_iso(H) = 1.2U_eq(N), while in (I) they were refined isotropically. The methyl groups were allowed to rotate about their local threefold axes.

Owing to the systematic absences analysed by the program XPREP (Sheldrick, 2008), (II) was solved and refined in the noncentrosymmetric space group Fdd2. No correlation matrix elements larger than 0.5 are observed. During structure validation with PLATON/ADDSYM (Le Page, 1987, 1988; Spek, 2009), an inversion centre at (0.126, 0.208, 0.466) was detected. However, refinement in the suggested space group C2/c was not satisfactory; the anisotropic displacement parameters of 12 atoms were nonpositive definite and the parameters of the recommended weighting scheme were unusually large (WGHT 0.0629 880.6169). Thus, the space group Fdd2 was retained.

Computing details

For all compounds, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008) and XP (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures

	Fig. 1. A perspective view of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Dashed lines indicate hydrogen bonds.
	Fig. 2. A packing diagram for (I). Dashed lines indicate hydrogen bonds.
	Fig. 3. Perspective views of (a) the first, (b) the second and (c) the third symmetry-independent complex in the asymmetric unit of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Dashed lines indicate hydrogen bonds.
	Fig. 4. A partial packing diagram for (II). Dashed lines indicate hydrogen bonds. The molecules are designated according to the atom numbering.
	Fig. 5. A perspective view of (III), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Dashed lines indicate hydrogen bonds.
	Fig. 6. A partial packing diagram for (III) showing chains of dimers running along the b axis. Dashed lines indicate hydrogen bonds.
	Fig. 7. A packing diagram for (III) showing the formation of tubes. Dashed lines indicate hydrogen bonds. [Please indicate the origin]

(I) 2-aminopyrimidine bis(6-propyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one)

Crystal data

C4H5N3·2C7H10N2OS	F(000) = 920
Mr = 435.57	Dx = 1.420 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.6094 (5) Å	Cell parameters from 18641 reflections
b = 12.9888 (6) Å	θ = 3.5–25.8°
c = 20.8838 (14) Å	µ = 0.29 mm^−1
β = 99.179 (5)°	T = 173 K
V = 2037.7 (2) Å^3	Block, colourless
Z = 4	0.60 × 0.20 × 0.15 mm

Data collection

Stoe IPDS II two-circle diffractometer	3819 independent reflections
Radiation source: fine-focus sealed tube	3163 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.094
ω scans	θmax = 25.6°, θmin = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −9→9
Tmin = 0.844, Tmax = 0.958	k = −15→14
25516 measured reflections	l = −25→25

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0617P)^2 + 0.2289P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3819 reflections	Δρmax = 0.30 e Å^−3
289 parameters	Δρmin = −0.29 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (6)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

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

	x	y	z	Uiso*/Ueq
N1	0.70342 (19)	0.49488 (12)	0.54717 (7)	0.0197 (3)
C2	0.7299 (2)	0.44500 (14)	0.49259 (8)	0.0188 (4)
N3	0.7939 (2)	0.48800 (12)	0.44186 (7)	0.0207 (3)
C4	0.8376 (3)	0.58776 (14)	0.44800 (9)	0.0238 (4)
H4	0.8828	0.6205	0.4134	0.029*
C5	0.8201 (3)	0.64541 (14)	0.50220 (9)	0.0249 (4)
H5	0.8550	0.7156	0.5061	0.030*
C6	0.7484 (2)	0.59469 (14)	0.55068 (9)	0.0216 (4)
H6	0.7305	0.6326	0.5880	0.026*
N21	0.6877 (2)	0.34417 (13)	0.48783 (9)	0.0280 (4)
H211	0.664 (3)	0.3122 (19)	0.5234 (11)	0.038 (6)*
H212	0.721 (3)	0.3089 (19)	0.4568 (12)	0.036 (6)*
N1A	0.9954 (2)	0.29340 (12)	0.25432 (7)	0.0181 (3)
H1A	1.009 (3)	0.2326 (18)	0.2442 (11)	0.029 (6)*
C2A	0.9322 (2)	0.31518 (13)	0.31017 (8)	0.0179 (4)
N3A	0.9080 (2)	0.41733 (11)	0.32194 (7)	0.0184 (3)
H3A	0.873 (3)	0.4340 (17)	0.3584 (11)	0.028 (6)*
C4A	0.9442 (2)	0.49830 (13)	0.28190 (8)	0.0187 (4)
C5A	1.0058 (2)	0.46774 (14)	0.22268 (9)	0.0215 (4)
H5A	1.0278	0.5185	0.1922	0.026*
C6A	1.0321 (2)	0.36715 (14)	0.21066 (8)	0.0195 (4)
S2A	0.88847 (6)	0.22183 (4)	0.36131 (2)	0.02233 (15)
O4A	0.92311 (18)	0.58839 (9)	0.29822 (6)	0.0246 (3)
C7A	1.1080 (3)	0.32542 (15)	0.15363 (10)	0.0293 (5)
H7A1	1.0447	0.2607	0.1395	0.035*
H7A2	1.2344	0.3076	0.1685	0.035*
C8A	1.0986 (3)	0.39622 (15)	0.09466 (9)	0.0256 (4)
H8A1	1.1863	0.3728	0.0675	0.031*
H8A2	1.1314	0.4670	0.1096	0.031*
C9A	0.9153 (3)	0.3977 (2)	0.05403 (12)	0.0458 (6)
H9A1	0.8825	0.3278	0.0389	0.069*
H9A2	0.9160	0.4431	0.0166	0.069*
H9A3	0.8286	0.4232	0.0803	0.069*
N1B	0.4997 (2)	0.31722 (12)	0.74197 (7)	0.0176 (3)
H1B	0.485 (3)	0.2579 (18)	0.7530 (11)	0.029 (6)*
C2B	0.5533 (2)	0.33663 (13)	0.68388 (8)	0.0182 (4)
N3B	0.57733 (19)	0.43775 (11)	0.67011 (7)	0.0184 (3)
H3B	0.611 (3)	0.4512 (17)	0.6328 (11)	0.028 (6)*
C4B	0.5526 (2)	0.52082 (13)	0.71078 (9)	0.0195 (4)
C5B	0.4991 (2)	0.49254 (14)	0.77175 (9)	0.0211 (4)
H5B	0.4822	0.5446	0.8021	0.025*
C6B	0.4729 (2)	0.39260 (13)	0.78597 (8)	0.0183 (4)
S2B	0.58686 (7)	0.24071 (4)	0.63318 (2)	0.02457 (15)
O4B	0.57692 (18)	0.61003 (10)	0.69342 (6)	0.0265 (3)
C7B	0.4101 (3)	0.35478 (14)	0.84640 (9)	0.0212 (4)
H7B1	0.4551	0.2839	0.8555	0.025*
H7B2	0.2784	0.3515	0.8383	0.025*
C8B	0.4680 (3)	0.42045 (16)	0.90602 (9)	0.0304 (5)
H8B1	0.4281	0.4923	0.8969	0.036*
H8B2	0.5995	0.4205	0.9165	0.036*
C9B	0.3900 (3)	0.37976 (16)	0.96403 (9)	0.0349 (5)
H9B1	0.2597	0.3825	0.9544	0.052*
H9B2	0.4318	0.4223	1.0022	0.052*
H9B3	0.4283	0.3084	0.9728	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0235 (8)	0.0186 (8)	0.0184 (7)	0.0016 (6)	0.0079 (6)	0.0003 (6)
C2	0.0204 (9)	0.0180 (9)	0.0186 (9)	0.0015 (7)	0.0051 (7)	0.0016 (7)
N3	0.0280 (8)	0.0180 (8)	0.0181 (8)	0.0016 (6)	0.0095 (6)	0.0010 (6)
C4	0.0314 (10)	0.0196 (10)	0.0231 (9)	0.0012 (8)	0.0131 (8)	0.0035 (7)
C5	0.0324 (10)	0.0153 (9)	0.0293 (10)	−0.0009 (8)	0.0118 (8)	−0.0008 (7)
C6	0.0253 (9)	0.0200 (9)	0.0207 (9)	0.0023 (7)	0.0075 (7)	−0.0026 (7)
N21	0.0447 (10)	0.0177 (8)	0.0260 (9)	−0.0049 (7)	0.0194 (8)	−0.0022 (7)
N1A	0.0262 (8)	0.0116 (8)	0.0178 (8)	0.0017 (6)	0.0072 (6)	−0.0010 (6)
C2A	0.0206 (8)	0.0159 (9)	0.0176 (8)	−0.0019 (7)	0.0045 (7)	−0.0018 (7)
N3A	0.0275 (8)	0.0141 (8)	0.0156 (7)	0.0013 (6)	0.0093 (6)	−0.0016 (6)
C4A	0.0228 (9)	0.0161 (9)	0.0180 (9)	0.0004 (7)	0.0051 (7)	0.0006 (7)
C5A	0.0289 (9)	0.0161 (9)	0.0215 (9)	0.0017 (7)	0.0098 (7)	0.0033 (7)
C6A	0.0233 (9)	0.0178 (9)	0.0185 (9)	0.0013 (7)	0.0069 (7)	0.0009 (7)
S2A	0.0343 (3)	0.0145 (3)	0.0206 (3)	−0.00223 (17)	0.01194 (19)	0.00127 (16)
O4A	0.0404 (8)	0.0132 (6)	0.0227 (7)	0.0006 (5)	0.0125 (6)	−0.0023 (5)
C7A	0.0451 (12)	0.0204 (10)	0.0268 (10)	0.0089 (9)	0.0192 (9)	0.0031 (8)
C8A	0.0359 (11)	0.0211 (10)	0.0237 (10)	−0.0023 (8)	0.0171 (8)	−0.0004 (8)
C9A	0.0465 (14)	0.0547 (16)	0.0368 (13)	−0.0054 (11)	0.0086 (10)	0.0132 (11)
N1B	0.0265 (8)	0.0125 (8)	0.0151 (7)	−0.0004 (6)	0.0069 (6)	0.0001 (6)
C2B	0.0204 (8)	0.0164 (9)	0.0182 (9)	0.0012 (7)	0.0045 (7)	0.0008 (7)
N3B	0.0276 (8)	0.0153 (8)	0.0139 (8)	−0.0003 (6)	0.0080 (6)	0.0008 (6)
C4B	0.0230 (9)	0.0155 (9)	0.0201 (9)	−0.0015 (7)	0.0043 (7)	−0.0004 (7)
C5B	0.0308 (10)	0.0146 (9)	0.0193 (9)	−0.0010 (7)	0.0085 (7)	−0.0025 (7)
C6B	0.0215 (9)	0.0160 (9)	0.0177 (9)	−0.0006 (7)	0.0041 (7)	−0.0010 (7)
S2B	0.0412 (3)	0.0152 (3)	0.0209 (3)	0.00032 (19)	0.0160 (2)	−0.00253 (17)
O4B	0.0431 (8)	0.0145 (7)	0.0239 (7)	−0.0021 (6)	0.0119 (6)	0.0023 (5)
C7B	0.0308 (10)	0.0162 (9)	0.0186 (9)	−0.0035 (7)	0.0101 (7)	−0.0013 (7)
C8B	0.0490 (12)	0.0244 (11)	0.0214 (10)	−0.0128 (9)	0.0163 (9)	−0.0048 (8)
C9B	0.0616 (14)	0.0259 (11)	0.0217 (10)	−0.0126 (10)	0.0202 (10)	−0.0052 (8)

Geometric parameters (Å, º)

N1—C6	1.340 (2)	C8A—C9A	1.513 (3)
N1—C2	1.354 (2)	C8A—H8A1	0.9900
C2—N21	1.348 (2)	C8A—H8A2	0.9900
C2—N3	1.355 (2)	C9A—H9A1	0.9800
N3—C4	1.339 (2)	C9A—H9A2	0.9800
C4—C5	1.381 (3)	C9A—H9A3	0.9800
C4—H4	0.9500	N1B—C2B	1.364 (2)
C5—C6	1.390 (3)	N1B—C6B	1.380 (2)
C5—H5	0.9500	N1B—H1B	0.82 (2)
C6—H6	0.9500	C2B—N3B	1.363 (2)
N21—H211	0.89 (2)	C2B—S2B	1.6807 (17)
N21—H212	0.87 (2)	N3B—C4B	1.404 (2)
N1A—C2A	1.361 (2)	N3B—H3B	0.88 (2)
N1A—C6A	1.381 (2)	C4B—O4B	1.237 (2)
N1A—H1A	0.83 (2)	C4B—C5B	1.445 (2)
C2A—N3A	1.367 (2)	C5B—C6B	1.353 (2)
C2A—S2A	1.6836 (18)	C5B—H5B	0.9500
N3A—C4A	1.398 (2)	C6B—C7B	1.502 (2)
N3A—H3A	0.87 (2)	C7B—C8B	1.516 (3)
C4A—O4A	1.236 (2)	C7B—H7B1	0.9900
C4A—C5A	1.446 (2)	C7B—H7B2	0.9900
C5A—C6A	1.351 (2)	C8B—C9B	1.526 (2)
C5A—H5A	0.9500	C8B—H8B1	0.9900
C6A—C7A	1.505 (2)	C8B—H8B2	0.9900
C7A—C8A	1.529 (3)	C9B—H9B1	0.9800
C7A—H7A1	0.9900	C9B—H9B2	0.9800
C7A—H7A2	0.9900	C9B—H9B3	0.9800
C6—N1—C2	115.98 (15)	C9A—C8A—H8A2	109.1
N21—C2—N1	117.45 (15)	H8A1—C8A—H8A2	107.9
N21—C2—N3	117.00 (16)	C8A—C9A—H9A1	109.5
N1—C2—N3	125.54 (17)	C8A—C9A—H9A2	109.5
C4—N3—C2	116.03 (15)	H9A1—C9A—H9A2	109.5
N3—C4—C5	123.26 (17)	C8A—C9A—H9A3	109.5
N3—C4—H4	118.4	H9A1—C9A—H9A3	109.5
C5—C4—H4	118.4	H9A2—C9A—H9A3	109.5
C4—C5—C6	116.12 (17)	C2B—N1B—C6B	123.92 (15)
C4—C5—H5	121.9	C2B—N1B—H1B	120.0 (16)
C6—C5—H5	121.9	C6B—N1B—H1B	116.0 (16)
N1—C6—C5	123.03 (17)	N1B—C2B—N3B	115.80 (15)
N1—C6—H6	118.5	N1B—C2B—S2B	121.36 (13)
C5—C6—H6	118.5	N3B—C2B—S2B	122.85 (13)
C2—N21—H211	117.9 (15)	C2B—N3B—C4B	125.26 (15)
C2—N21—H212	118.3 (16)	C2B—N3B—H3B	116.6 (15)
H211—N21—H212	120 (2)	C4B—N3B—H3B	118.2 (15)
C2A—N1A—C6A	123.91 (15)	O4B—C4B—N3B	120.12 (16)
C2A—N1A—H1A	119.5 (15)	O4B—C4B—C5B	124.95 (16)
C6A—N1A—H1A	116.5 (15)	N3B—C4B—C5B	114.93 (15)
N3A—C2A—N1A	115.60 (15)	C6B—C5B—C4B	120.62 (16)
N3A—C2A—S2A	122.62 (13)	C6B—C5B—H5B	119.7
N1A—C2A—S2A	121.78 (13)	C4B—C5B—H5B	119.7
C2A—N3A—C4A	125.28 (15)	C5B—C6B—N1B	119.46 (16)
C2A—N3A—H3A	117.8 (15)	C5B—C6B—C7B	125.16 (16)
C4A—N3A—H3A	116.9 (15)	N1B—C6B—C7B	115.35 (15)
O4A—C4A—N3A	120.03 (15)	C6B—C7B—C8B	114.62 (15)
O4A—C4A—C5A	124.72 (16)	C6B—C7B—H7B1	108.6
N3A—C4A—C5A	115.25 (15)	C8B—C7B—H7B1	108.6
C6A—C5A—C4A	120.14 (16)	C6B—C7B—H7B2	108.6
C6A—C5A—H5A	119.9	C8B—C7B—H7B2	108.6
C4A—C5A—H5A	119.9	H7B1—C7B—H7B2	107.6
C5A—C6A—N1A	119.76 (16)	C7B—C8B—C9B	111.01 (16)
C5A—C6A—C7A	125.60 (17)	C7B—C8B—H8B1	109.4
N1A—C6A—C7A	114.58 (15)	C9B—C8B—H8B1	109.4
C6A—C7A—C8A	116.50 (16)	C7B—C8B—H8B2	109.4
C6A—C7A—H7A1	108.2	C9B—C8B—H8B2	109.4
C8A—C7A—H7A1	108.2	H8B1—C8B—H8B2	108.0
C6A—C7A—H7A2	108.2	C8B—C9B—H9B1	109.5
C8A—C7A—H7A2	108.2	C8B—C9B—H9B2	109.5
H7A1—C7A—H7A2	107.3	H9B1—C9B—H9B2	109.5
C7A—C8A—C9A	112.32 (17)	C8B—C9B—H9B3	109.5
C7A—C8A—H8A1	109.1	H9B1—C9B—H9B3	109.5
C9A—C8A—H8A1	109.1	H9B2—C9B—H9B3	109.5
C7A—C8A—H8A2	109.1
C6—N1—C2—N21	179.34 (16)	C2A—N1A—C6A—C7A	177.62 (17)
C6—N1—C2—N3	−1.3 (3)	C5A—C6A—C7A—C8A	−20.7 (3)
N21—C2—N3—C4	−179.01 (17)	N1A—C6A—C7A—C8A	162.10 (17)
N1—C2—N3—C4	1.6 (3)	C6A—C7A—C8A—C9A	−78.4 (2)
C2—N3—C4—C5	0.1 (3)	C6B—N1B—C2B—N3B	−1.1 (3)
N3—C4—C5—C6	−1.8 (3)	C6B—N1B—C2B—S2B	178.90 (13)
C2—N1—C6—C5	−0.7 (3)	N1B—C2B—N3B—C4B	0.5 (3)
C4—C5—C6—N1	2.2 (3)	S2B—C2B—N3B—C4B	−179.49 (14)
C6A—N1A—C2A—N3A	−0.9 (3)	C2B—N3B—C4B—O4B	−179.51 (17)
C6A—N1A—C2A—S2A	179.54 (13)	C2B—N3B—C4B—C5B	0.6 (2)
N1A—C2A—N3A—C4A	−0.5 (3)	O4B—C4B—C5B—C6B	178.89 (18)
S2A—C2A—N3A—C4A	179.04 (14)	N3B—C4B—C5B—C6B	−1.2 (3)
C2A—N3A—C4A—O4A	−177.58 (16)	C4B—C5B—C6B—N1B	0.7 (3)
C2A—N3A—C4A—C5A	2.3 (3)	C4B—C5B—C6B—C7B	−177.31 (16)
O4A—C4A—C5A—C6A	177.03 (18)	C2B—N1B—C6B—C5B	0.5 (3)
N3A—C4A—C5A—C6A	−2.9 (3)	C2B—N1B—C6B—C7B	178.74 (16)
C4A—C5A—C6A—N1A	1.7 (3)	C5B—C6B—C7B—C8B	−31.6 (3)
C4A—C5A—C6A—C7A	−175.31 (17)	N1B—C6B—C7B—C8B	150.28 (17)
C2A—N1A—C6A—C5A	0.3 (3)	C6B—C7B—C8B—C9B	176.90 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H211···S2B	0.89 (2)	2.63 (2)	3.5145 (17)	173 (2)
N21—H212···S2A	0.87 (2)	2.77 (2)	3.6234 (18)	168 (2)
N1A—H1A···O4A^i	0.83 (2)	2.17 (2)	2.983 (2)	167 (2)
N3A—H3A···N3	0.87 (2)	2.06 (2)	2.926 (2)	174 (2)
N1B—H1B···O4B^ii	0.82 (2)	2.31 (2)	3.107 (2)	166 (2)
N3B—H3B···N1	0.88 (2)	2.10 (2)	2.975 (2)	175 (2)

Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+1, y−1/2, −z+3/2.

(II) N-(6-acetamidopyridin-2-yl)acetamide bis(6-propyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one)

Crystal data

C9H11N3O2·2C7H10N2OS	Dx = 1.380 Mg m^−3
Mr = 533.67	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fdd2	Cell parameters from 37383 reflections
a = 37.9355 (12) Å	θ = 3.3–25.9°
b = 76.880 (3) Å	µ = 0.25 mm^−1
c = 10.5666 (3) Å	T = 173 K
V = 30817.3 (18) Å^3	Block, colourless
Z = 48	0.50 × 0.30 × 0.20 mm
F(000) = 13536

Data collection

Stoe IPDS II two-circle diffractometer	14445 independent reflections
Radiation source: fine-focus sealed tube	10225 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.129
ω scans	θmax = 25.7°, θmin = 3.3°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −45→46
Tmin = 0.885, Tmax = 0.951	k = −93→93
108254 measured reflections	l = −12→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0392P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.91	(Δ/σ)max = 0.002
14445 reflections	Δρmax = 0.22 e Å^−3
985 parameters	Δρmin = −0.25 e Å^−3
1 restraint	Absolute structure: Flack (1983), 6784 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.12 (7)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(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
N1A	0.04637 (8)	0.41911 (4)	0.3404 (3)	0.0205 (7)
C2A	0.06441 (11)	0.43341 (5)	0.3765 (3)	0.0210 (9)
C3A	0.10109 (12)	0.43423 (6)	0.3785 (4)	0.0293 (10)
H3A	0.1131	0.4445	0.4048	0.035*
C4A	0.11922 (11)	0.41971 (6)	0.3409 (5)	0.0323 (10)
H4A	0.1443	0.4200	0.3402	0.039*
C5A	0.10196 (12)	0.40476 (5)	0.3041 (4)	0.0270 (10)
H5A	0.1145	0.3947	0.2785	0.032*
C6A	0.06491 (12)	0.40519 (5)	0.3064 (3)	0.0223 (9)
N21A	0.04261 (10)	0.44734 (4)	0.4136 (3)	0.0240 (7)
H21A	0.0202	0.4448	0.4258	0.029*
C22A	0.05194 (11)	0.46425 (5)	0.4327 (3)	0.0235 (9)
C23A	0.02307 (12)	0.47639 (6)	0.4719 (4)	0.0354 (10)
H23A	0.0327	0.4853	0.5284	0.053*
H23B	0.0047	0.4698	0.5163	0.053*
H23C	0.0130	0.4819	0.3967	0.053*
O24A	0.08282 (8)	0.46960 (4)	0.4170 (3)	0.0334 (7)
N61A	0.04430 (10)	0.39090 (4)	0.2680 (3)	0.0222 (7)
H61A	0.0219	0.3931	0.2526	0.027*
C62A	0.05486 (12)	0.37402 (5)	0.2519 (4)	0.0249 (9)
C63A	0.02653 (12)	0.36131 (5)	0.2129 (4)	0.0315 (10)
H63A	0.0321	0.3566	0.1290	0.047*
H63B	0.0037	0.3673	0.2100	0.047*
H63C	0.0254	0.3518	0.2744	0.047*
O64A	0.08540 (9)	0.36925 (4)	0.2725 (3)	0.0359 (7)
N1B	0.29331 (10)	0.50438 (4)	0.6043 (3)	0.0198 (7)
C2B	0.31130 (11)	0.51879 (5)	0.5776 (3)	0.0210 (9)
C3B	0.34789 (12)	0.51984 (6)	0.5756 (4)	0.0275 (10)
H3B	0.3597	0.5304	0.5560	0.033*
C4B	0.36629 (13)	0.50483 (6)	0.6033 (5)	0.0348 (11)
H4B	0.3913	0.5050	0.6021	0.042*
C5B	0.34889 (12)	0.48959 (6)	0.6326 (4)	0.0279 (10)
H5B	0.3615	0.4793	0.6532	0.033*
C6B	0.31265 (12)	0.48984 (5)	0.6310 (3)	0.0227 (9)
N21B	0.28956 (10)	0.53334 (4)	0.5495 (3)	0.0225 (8)
H21B	0.2671	0.5312	0.5367	0.027*
C22B	0.29998 (12)	0.55044 (5)	0.5400 (3)	0.0235 (9)
C23B	0.27049 (13)	0.56306 (6)	0.5079 (4)	0.0341 (10)
H23D	0.2664	0.5709	0.5798	0.051*
H23E	0.2489	0.5565	0.4897	0.051*
H23F	0.2771	0.5699	0.4335	0.051*
O24B	0.33021 (8)	0.55548 (4)	0.5558 (3)	0.0324 (7)
N61B	0.29157 (9)	0.47512 (4)	0.6587 (3)	0.0234 (8)
H61B	0.2691	0.4771	0.6735	0.028*
C62B	0.30265 (11)	0.45815 (5)	0.6649 (3)	0.0230 (9)
C63B	0.27454 (12)	0.44515 (5)	0.6982 (4)	0.0326 (10)
H63D	0.2638	0.4406	0.6205	0.049*
H63E	0.2564	0.4508	0.7498	0.049*
H63F	0.2851	0.4355	0.7461	0.049*
O64B	0.33312 (8)	0.45376 (4)	0.6441 (3)	0.0326 (7)
N1C	0.53966 (7)	0.58569 (5)	0.3414 (3)	0.0215 (6)
C2C	0.55780 (12)	0.60074 (5)	0.3528 (3)	0.0217 (9)
C3C	0.59398 (14)	0.60159 (6)	0.3500 (5)	0.0368 (11)
H3C	0.6060	0.6123	0.3596	0.044*
C4C	0.61234 (11)	0.58609 (7)	0.3324 (6)	0.0448 (12)
H4C	0.6373	0.5863	0.3275	0.054*
C5C	0.59504 (12)	0.57067 (6)	0.3221 (4)	0.0336 (11)
H5C	0.6076	0.5600	0.3126	0.040*
C6C	0.55822 (11)	0.57096 (5)	0.3261 (3)	0.0201 (8)
N21C	0.53634 (10)	0.61562 (4)	0.3698 (3)	0.0233 (8)
H21C	0.5138	0.6137	0.3846	0.028*
C22C	0.54652 (12)	0.63266 (5)	0.3660 (4)	0.0245 (9)
C23C	0.51835 (13)	0.64592 (6)	0.3921 (4)	0.0350 (11)
H23G	0.5203	0.6499	0.4799	0.052*
H23H	0.4951	0.6407	0.3789	0.052*
H23I	0.5213	0.6558	0.3347	0.052*
O24C	0.57706 (8)	0.63735 (4)	0.3401 (3)	0.0290 (7)
N61C	0.53781 (10)	0.55587 (4)	0.3123 (3)	0.0247 (8)
H61C	0.5152	0.5575	0.2982	0.030*
C62C	0.54898 (11)	0.53895 (5)	0.3182 (3)	0.0237 (9)
C63C	0.52117 (12)	0.52517 (5)	0.2950 (4)	0.0331 (10)
H63G	0.5308	0.5161	0.2395	0.050*
H63H	0.5006	0.5305	0.2546	0.050*
H63I	0.5142	0.5200	0.3758	0.050*
O64C	0.57937 (8)	0.53474 (3)	0.3428 (2)	0.0302 (7)
N1'A	0.13439 (9)	0.49684 (4)	0.4535 (3)	0.0209 (7)
H1'A	0.1164	0.4897	0.4486	0.025*
C2'A	0.12755 (11)	0.51404 (5)	0.4722 (3)	0.0211 (8)
N3'A	0.15686 (9)	0.52431 (4)	0.4775 (3)	0.0218 (7)
H3'A	0.1533	0.5356	0.4856	0.026*
C4'A	0.19187 (11)	0.51875 (5)	0.4714 (3)	0.0230 (9)
C5'A	0.19626 (11)	0.50059 (5)	0.4509 (3)	0.0234 (9)
H5'A	0.2193	0.4958	0.4436	0.028*
C6'A	0.16765 (11)	0.48996 (5)	0.4418 (3)	0.0209 (8)
S2'A	0.08665 (3)	0.521886 (13)	0.48871 (10)	0.0289 (2)
O4'A	0.21543 (8)	0.52978 (4)	0.4852 (3)	0.0303 (7)
C7'A	0.16891 (11)	0.47065 (5)	0.4192 (3)	0.0223 (8)
H7'1	0.1550	0.4680	0.3422	0.027*
H7'2	0.1573	0.4647	0.4912	0.027*
C8'A	0.20564 (11)	0.46300 (5)	0.4032 (4)	0.0298 (9)
H8'1	0.2195	0.4650	0.4812	0.036*
H8'2	0.2178	0.4689	0.3323	0.036*
C9'A	0.20376 (12)	0.44355 (6)	0.3768 (4)	0.0363 (11)
H9'1	0.1940	0.4376	0.4508	0.054*
H9'2	0.2275	0.4391	0.3594	0.054*
H9'3	0.1886	0.4415	0.3033	0.054*
N1'B	0.38184 (10)	0.58121 (4)	0.4941 (3)	0.0213 (7)
H1'B	0.3637	0.5742	0.5018	0.026*
C2'B	0.37563 (12)	0.59809 (5)	0.4675 (3)	0.0203 (9)
N3'B	0.40486 (10)	0.60829 (4)	0.4569 (3)	0.0238 (8)
H3'B	0.4014	0.6195	0.4435	0.029*
C4'B	0.43985 (12)	0.60269 (5)	0.4653 (4)	0.0214 (9)
C5'B	0.44406 (12)	0.58472 (5)	0.4949 (4)	0.0243 (9)
H5'B	0.4671	0.5800	0.5039	0.029*
C6'B	0.41576 (12)	0.57434 (5)	0.5102 (3)	0.0209 (9)
S2'B	0.33509 (3)	0.606102 (13)	0.44351 (9)	0.0257 (2)
O4'B	0.46371 (8)	0.61343 (4)	0.4453 (3)	0.0311 (7)
C7'B	0.41645 (12)	0.55538 (5)	0.5413 (4)	0.0242 (9)
H7'3	0.4051	0.5489	0.4713	0.029*
H7'4	0.4022	0.5534	0.6184	0.029*
C8'B	0.45326 (12)	0.54784 (5)	0.5632 (4)	0.0263 (9)
H8'3	0.4650	0.5543	0.6327	0.032*
H8'4	0.4676	0.5493	0.4857	0.032*
C9'B	0.45136 (13)	0.52837 (6)	0.5973 (4)	0.0337 (10)
H9'4	0.4359	0.5268	0.6707	0.050*
H9'5	0.4750	0.5241	0.6176	0.050*
H9'6	0.4419	0.5218	0.5252	0.050*
N1'C	0.63084 (9)	0.66318 (4)	0.4136 (3)	0.0203 (7)
H1'C	0.6123	0.6565	0.4005	0.024*
C2'C	0.62536 (11)	0.68026 (5)	0.4414 (3)	0.0194 (8)
N3'C	0.65513 (9)	0.68986 (4)	0.4591 (3)	0.0209 (7)
H3'C	0.6523	0.7011	0.4730	0.025*
C4'C	0.68971 (11)	0.68358 (5)	0.4571 (3)	0.0227 (9)
C5'C	0.69303 (12)	0.66564 (5)	0.4251 (3)	0.0226 (9)
H5'C	0.7158	0.6606	0.4178	0.027*
C6'C	0.66410 (11)	0.65572 (5)	0.4051 (3)	0.0190 (8)
S2'C	0.58490 (3)	0.688842 (13)	0.45544 (9)	0.0266 (2)
O4'C	0.71390 (8)	0.69381 (4)	0.4805 (3)	0.0280 (7)
C7'C	0.66410 (12)	0.63658 (5)	0.3752 (4)	0.0230 (9)
H7'5	0.6505	0.6347	0.2964	0.028*
H7'6	0.6517	0.6303	0.4441	0.028*
C8'C	0.70052 (12)	0.62859 (5)	0.3587 (4)	0.0289 (10)
H8'5	0.7128	0.6343	0.2872	0.035*
H8'6	0.7146	0.6306	0.4362	0.035*
C9'C	0.69790 (14)	0.60927 (6)	0.3334 (5)	0.0406 (12)
H9'7	0.6879	0.6034	0.4076	0.061*
H9'8	0.7214	0.6046	0.3161	0.061*
H9'9	0.6826	0.6073	0.2600	0.061*
N1'D	0.11197 (9)	0.59257 (4)	0.5034 (3)	0.0234 (7)
H1'D	0.1303	0.5996	0.5052	0.028*
C2'D	0.11786 (10)	0.57519 (5)	0.4990 (3)	0.0204 (8)
N3'D	0.08833 (9)	0.56501 (4)	0.4948 (3)	0.0235 (7)
H3'D	0.0915	0.5537	0.4925	0.028*
C4'D	0.05337 (11)	0.57097 (5)	0.4937 (4)	0.0252 (9)
C5'D	0.04972 (11)	0.58954 (5)	0.5003 (4)	0.0250 (9)
H5'D	0.0269	0.5946	0.5013	0.030*
C6'D	0.07851 (10)	0.59991 (5)	0.5053 (3)	0.0187 (8)
S2'D	0.15874 (3)	0.566847 (13)	0.49901 (11)	0.0322 (2)
O4'D	0.02949 (8)	0.56006 (4)	0.4886 (3)	0.0310 (7)
C7'D	0.07832 (11)	0.61952 (5)	0.5136 (4)	0.0242 (9)
H7'7	0.0900	0.6229	0.5936	0.029*
H7'8	0.0928	0.6241	0.4433	0.029*
C8'D	0.04280 (12)	0.62824 (5)	0.5086 (4)	0.0314 (10)
H8'7	0.0277	0.6237	0.5776	0.038*
H8'8	0.0312	0.6255	0.4270	0.038*
C9'D	0.04670 (12)	0.64801 (5)	0.5227 (4)	0.0351 (10)
H9'X	0.0559	0.6507	0.6071	0.053*
H9'Y	0.0236	0.6536	0.5116	0.053*
H9'Z	0.0631	0.6524	0.4583	0.053*
N1'E	0.36296 (9)	0.67688 (4)	0.4185 (3)	0.0205 (7)
H1'E	0.3817	0.6836	0.4153	0.025*
C2'E	0.36797 (12)	0.65940 (5)	0.4210 (4)	0.0237 (9)
N3'E	0.33807 (10)	0.64972 (4)	0.4297 (3)	0.0238 (8)
H3'E	0.3408	0.6384	0.4336	0.029*
C4'E	0.30356 (11)	0.65599 (5)	0.4332 (4)	0.0216 (9)
C5'E	0.30064 (11)	0.67473 (5)	0.4282 (4)	0.0233 (9)
H5'E	0.2780	0.6800	0.4302	0.028*
C6'E	0.32987 (12)	0.68475 (5)	0.4208 (3)	0.0220 (9)
S2'E	0.40831 (3)	0.650629 (14)	0.41640 (11)	0.0315 (3)
O4'E	0.27904 (8)	0.64556 (4)	0.4411 (3)	0.0315 (7)
C7'E	0.33083 (11)	0.70422 (5)	0.4139 (3)	0.0228 (8)
H7'9	0.3425	0.7077	0.3339	0.027*
H7'X	0.3455	0.7086	0.4845	0.027*
C8'E	0.29459 (11)	0.71310 (5)	0.4200 (4)	0.0303 (10)
H8'9	0.2831	0.7104	0.5020	0.036*
H8'X	0.2793	0.7086	0.3513	0.036*
C9'E	0.29917 (13)	0.73295 (6)	0.4060 (5)	0.0417 (12)
H9'A	0.3147	0.7373	0.4730	0.063*
H9'B	0.2761	0.7386	0.4127	0.063*
H9'C	0.3096	0.7356	0.3232	0.063*
N1'F	0.61587 (9)	0.75861 (4)	0.5395 (3)	0.0213 (7)
H1'F	0.6347	0.7651	0.5501	0.026*
C2'F	0.62052 (11)	0.74121 (5)	0.5208 (3)	0.0208 (9)
N3'F	0.59025 (9)	0.73191 (4)	0.5054 (3)	0.0211 (7)
H3'F	0.5926	0.7206	0.4940	0.025*
C4'F	0.55616 (11)	0.73843 (5)	0.5060 (4)	0.0236 (9)
C5'F	0.55347 (11)	0.75687 (5)	0.5256 (3)	0.0224 (9)
H5'F	0.5310	0.7623	0.5266	0.027*
C6'F	0.58300 (11)	0.76663 (5)	0.5426 (3)	0.0200 (8)
S2'F	0.66055 (3)	0.732086 (13)	0.51839 (10)	0.0279 (2)
O4'F	0.53115 (8)	0.72836 (3)	0.4878 (3)	0.0298 (7)
C7'F	0.58398 (12)	0.78580 (5)	0.5630 (4)	0.0259 (9)
H7'Y	0.5975	0.7911	0.4928	0.031*
H7'Z	0.5971	0.7881	0.6422	0.031*
C8'F	0.54838 (12)	0.79484 (5)	0.5712 (4)	0.0323 (10)
H8'Y	0.5346	0.7898	0.6417	0.039*
H8'Z	0.5351	0.7928	0.4918	0.039*
C9'F	0.55272 (13)	0.81434 (5)	0.5925 (5)	0.0425 (12)
H9'D	0.5655	0.8163	0.6717	0.064*
H9'E	0.5294	0.8198	0.5976	0.064*
H9'F	0.5660	0.8194	0.5220	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0183 (15)	0.0184 (18)	0.0248 (14)	−0.0009 (14)	−0.0025 (15)	−0.0015 (12)
C2A	0.022 (2)	0.018 (2)	0.0230 (18)	−0.0036 (16)	0.0004 (15)	−0.0020 (14)
C3A	0.020 (2)	0.025 (2)	0.043 (2)	−0.0026 (18)	−0.0082 (17)	−0.0020 (17)
C4A	0.018 (2)	0.024 (3)	0.054 (2)	0.0000 (18)	−0.005 (2)	−0.008 (2)
C5A	0.018 (2)	0.018 (2)	0.045 (2)	0.0021 (17)	−0.0018 (17)	−0.0069 (17)
C6A	0.023 (2)	0.020 (2)	0.0244 (18)	−0.0025 (17)	−0.0037 (16)	−0.0007 (15)
N21A	0.0175 (18)	0.0208 (18)	0.0337 (17)	−0.0009 (14)	0.0039 (13)	−0.0044 (13)
C22A	0.026 (2)	0.020 (2)	0.0243 (18)	−0.0038 (17)	−0.0007 (16)	−0.0013 (15)
C23A	0.030 (2)	0.026 (2)	0.051 (3)	−0.0003 (19)	0.002 (2)	−0.0077 (18)
O24A	0.0224 (16)	0.0236 (16)	0.0543 (17)	−0.0057 (12)	0.0059 (13)	−0.0070 (13)
N61A	0.0171 (19)	0.0167 (18)	0.0327 (16)	0.0020 (13)	−0.0038 (13)	−0.0037 (13)
C62A	0.022 (2)	0.022 (2)	0.0309 (19)	−0.0036 (17)	0.0022 (17)	−0.0025 (16)
C63A	0.025 (2)	0.021 (2)	0.048 (2)	−0.0004 (18)	−0.0025 (19)	−0.0044 (18)
O64A	0.0222 (18)	0.0185 (16)	0.0669 (19)	0.0058 (13)	−0.0019 (14)	−0.0039 (13)
N1B	0.0157 (18)	0.0188 (17)	0.0251 (15)	−0.0008 (14)	0.0017 (13)	0.0031 (12)
C2B	0.018 (2)	0.022 (2)	0.0230 (18)	0.0014 (17)	−0.0033 (16)	−0.0035 (15)
C3B	0.018 (2)	0.016 (2)	0.049 (2)	−0.0023 (16)	0.0010 (18)	0.0007 (17)
C4B	0.013 (2)	0.030 (3)	0.062 (3)	−0.0021 (19)	−0.002 (2)	0.001 (2)
C5B	0.020 (2)	0.021 (2)	0.042 (2)	0.0032 (18)	0.0031 (17)	0.0024 (17)
C6B	0.021 (2)	0.017 (2)	0.0294 (19)	−0.0018 (17)	0.0008 (16)	−0.0008 (15)
N21B	0.0174 (19)	0.0163 (18)	0.0336 (17)	−0.0015 (14)	−0.0045 (13)	0.0038 (13)
C22B	0.025 (2)	0.019 (2)	0.0261 (19)	−0.0021 (17)	−0.0020 (15)	0.0018 (15)
C23B	0.030 (3)	0.022 (2)	0.050 (2)	0.0023 (18)	−0.014 (2)	0.0028 (19)
O24B	0.0217 (17)	0.0247 (16)	0.0508 (17)	−0.0074 (12)	−0.0031 (13)	0.0021 (12)
N61B	0.0113 (17)	0.0197 (18)	0.0391 (18)	0.0025 (13)	0.0070 (14)	0.0040 (14)
C62B	0.022 (2)	0.018 (2)	0.0284 (19)	0.0052 (16)	0.0011 (16)	0.0034 (15)
C63B	0.025 (2)	0.018 (2)	0.056 (3)	0.0046 (17)	0.0106 (19)	0.0047 (19)
O64B	0.0192 (16)	0.0247 (16)	0.0540 (17)	0.0052 (13)	0.0066 (13)	0.0051 (13)
N1C	0.0192 (15)	0.0178 (18)	0.0275 (13)	0.0017 (15)	0.0019 (15)	0.0006 (12)
C2C	0.020 (2)	0.024 (2)	0.0213 (18)	0.0025 (18)	−0.0016 (15)	0.0001 (15)
C3C	0.028 (3)	0.021 (2)	0.062 (3)	−0.0048 (19)	−0.002 (2)	−0.005 (2)
C4C	0.0122 (19)	0.040 (3)	0.083 (3)	0.001 (2)	−0.001 (3)	0.004 (2)
C5C	0.014 (2)	0.024 (2)	0.062 (3)	0.0028 (18)	0.0038 (19)	−0.001 (2)
C6C	0.013 (2)	0.024 (2)	0.0227 (17)	0.0013 (16)	−0.0028 (15)	0.0011 (15)
N21C	0.0125 (18)	0.0211 (19)	0.0362 (18)	0.0026 (14)	0.0034 (13)	−0.0025 (13)
C22C	0.020 (2)	0.025 (2)	0.0286 (19)	−0.0032 (17)	0.0003 (16)	−0.0026 (16)
C23C	0.031 (3)	0.026 (2)	0.048 (2)	−0.0017 (19)	0.011 (2)	−0.0053 (18)
O24C	0.0230 (17)	0.0215 (15)	0.0427 (15)	−0.0057 (12)	0.0043 (12)	−0.0034 (12)
N61C	0.0155 (18)	0.0228 (19)	0.0358 (17)	0.0023 (14)	−0.0045 (14)	−0.0010 (13)
C62C	0.020 (2)	0.023 (2)	0.0273 (19)	0.0007 (16)	−0.0016 (16)	−0.0022 (16)
C63C	0.029 (2)	0.023 (2)	0.048 (2)	−0.0019 (18)	−0.0073 (19)	−0.0069 (18)
O64C	0.0236 (16)	0.0236 (15)	0.0433 (15)	0.0071 (12)	−0.0057 (12)	−0.0057 (12)
N1'A	0.0151 (17)	0.0177 (18)	0.0298 (16)	−0.0030 (13)	−0.0024 (13)	0.0009 (12)
C2'A	0.019 (2)	0.017 (2)	0.0266 (18)	−0.0063 (16)	−0.0002 (15)	0.0033 (14)
N3'A	0.0170 (18)	0.0156 (17)	0.0329 (16)	−0.0017 (13)	−0.0044 (14)	0.0004 (12)
C4'A	0.017 (2)	0.023 (2)	0.029 (2)	−0.0025 (17)	0.0005 (15)	0.0063 (16)
C5'A	0.017 (2)	0.025 (2)	0.0290 (19)	0.0013 (17)	−0.0011 (15)	0.0018 (16)
C6'A	0.022 (2)	0.017 (2)	0.0233 (17)	0.0016 (16)	−0.0024 (15)	0.0022 (14)
S2'A	0.0172 (5)	0.0218 (5)	0.0478 (6)	−0.0001 (4)	−0.0004 (5)	0.0026 (4)
O4'A	0.0162 (16)	0.0244 (16)	0.0502 (17)	−0.0042 (12)	−0.0025 (13)	−0.0006 (13)
C7'A	0.020 (2)	0.017 (2)	0.0296 (18)	−0.0018 (16)	−0.0017 (15)	−0.0022 (15)
C8'A	0.025 (2)	0.026 (2)	0.039 (2)	0.0018 (18)	−0.0005 (17)	−0.0046 (17)
C9'A	0.025 (2)	0.025 (2)	0.058 (3)	0.0035 (19)	0.009 (2)	−0.0163 (19)
N1'B	0.0165 (19)	0.0191 (18)	0.0285 (16)	−0.0020 (14)	0.0004 (13)	0.0017 (13)
C2'B	0.024 (2)	0.015 (2)	0.0214 (18)	−0.0001 (17)	−0.0010 (15)	−0.0020 (14)
N3'B	0.021 (2)	0.0169 (18)	0.0333 (17)	0.0007 (14)	0.0004 (15)	0.0000 (14)
C4'B	0.018 (2)	0.015 (2)	0.031 (2)	−0.0017 (16)	0.0049 (16)	−0.0048 (15)
C5'B	0.021 (3)	0.020 (2)	0.033 (2)	0.0005 (17)	0.0000 (17)	0.0015 (16)
C6'B	0.021 (2)	0.023 (2)	0.0189 (16)	0.0057 (17)	−0.0041 (15)	−0.0004 (14)
S2'B	0.0173 (5)	0.0177 (5)	0.0421 (5)	0.0003 (4)	−0.0012 (4)	−0.0005 (4)
O4'B	0.0211 (18)	0.0221 (16)	0.0503 (17)	−0.0074 (13)	0.0069 (14)	−0.0003 (13)
C7'B	0.022 (2)	0.019 (2)	0.032 (2)	−0.0029 (17)	−0.0033 (16)	0.0012 (15)
C8'B	0.025 (2)	0.018 (2)	0.035 (2)	−0.0009 (17)	−0.0016 (17)	0.0031 (16)
C9'B	0.028 (3)	0.022 (2)	0.051 (3)	−0.0058 (19)	−0.007 (2)	0.0037 (19)
N1'C	0.0147 (18)	0.0183 (17)	0.0278 (16)	−0.0026 (13)	−0.0004 (12)	−0.0028 (13)
C2'C	0.015 (2)	0.019 (2)	0.0235 (17)	−0.0052 (15)	0.0012 (15)	0.0044 (14)
N3'C	0.0175 (18)	0.0132 (17)	0.0320 (16)	0.0003 (13)	−0.0008 (13)	−0.0042 (12)
C4'C	0.019 (2)	0.022 (2)	0.0273 (18)	−0.0016 (17)	−0.0029 (16)	0.0038 (15)
C5'C	0.015 (2)	0.020 (2)	0.033 (2)	0.0032 (16)	0.0021 (16)	0.0015 (16)
C6'C	0.018 (2)	0.015 (2)	0.0241 (17)	−0.0018 (16)	−0.0014 (15)	0.0029 (14)
S2'C	0.0166 (5)	0.0210 (5)	0.0422 (5)	0.0012 (4)	0.0001 (4)	−0.0007 (4)
O4'C	0.0198 (16)	0.0219 (15)	0.0424 (16)	−0.0028 (12)	−0.0044 (12)	−0.0007 (12)
C7'C	0.022 (2)	0.019 (2)	0.0285 (18)	0.0012 (17)	0.0011 (16)	−0.0024 (15)
C8'C	0.020 (2)	0.024 (2)	0.042 (2)	−0.0006 (18)	0.0020 (17)	−0.0034 (18)
C9'C	0.029 (3)	0.029 (3)	0.063 (3)	0.007 (2)	0.005 (2)	−0.006 (2)
N1'D	0.0189 (19)	0.0174 (18)	0.0340 (16)	−0.0031 (14)	−0.0001 (14)	0.0001 (13)
C2'D	0.014 (2)	0.020 (2)	0.0278 (18)	−0.0008 (16)	−0.0022 (15)	−0.0002 (16)
N3'D	0.0194 (19)	0.0150 (17)	0.0360 (16)	−0.0002 (14)	−0.0017 (15)	0.0008 (13)
C4'D	0.019 (2)	0.028 (2)	0.0283 (19)	−0.0009 (18)	0.0015 (17)	0.0045 (17)
C5'D	0.018 (2)	0.025 (2)	0.0321 (19)	0.0008 (17)	−0.0010 (16)	0.0027 (17)
C6'D	0.017 (2)	0.018 (2)	0.0206 (16)	0.0019 (16)	0.0006 (15)	0.0010 (14)
S2'D	0.0173 (5)	0.0199 (6)	0.0594 (6)	0.0001 (4)	−0.0012 (5)	0.0007 (5)
O4'D	0.0209 (17)	0.0254 (16)	0.0468 (15)	−0.0086 (13)	−0.0031 (13)	0.0048 (12)
C7'D	0.023 (2)	0.018 (2)	0.0318 (19)	−0.0028 (16)	0.0006 (16)	−0.0012 (15)
C8'D	0.028 (2)	0.020 (2)	0.047 (2)	0.0019 (18)	0.0035 (19)	0.0022 (19)
C9'D	0.029 (3)	0.020 (2)	0.057 (3)	−0.0010 (18)	0.006 (2)	−0.0036 (19)
N1'E	0.0163 (19)	0.0132 (17)	0.0321 (16)	−0.0007 (13)	0.0019 (13)	0.0011 (13)
C2'E	0.026 (3)	0.017 (2)	0.0285 (19)	−0.0011 (18)	0.0030 (17)	−0.0012 (16)
N3'E	0.018 (2)	0.0149 (18)	0.0388 (17)	−0.0025 (14)	0.0026 (15)	−0.0009 (14)
C4'E	0.017 (2)	0.019 (2)	0.0283 (19)	−0.0022 (17)	0.0050 (17)	−0.0022 (16)
C5'E	0.012 (2)	0.021 (2)	0.037 (2)	−0.0004 (16)	−0.0021 (16)	−0.0008 (17)
C6'E	0.021 (2)	0.021 (2)	0.0238 (18)	0.0035 (17)	0.0022 (16)	0.0031 (15)
S2'E	0.0175 (6)	0.0191 (6)	0.0581 (7)	0.0012 (4)	0.0041 (5)	0.0013 (5)
O4'E	0.0189 (18)	0.0213 (16)	0.0543 (18)	−0.0036 (13)	0.0064 (14)	−0.0058 (13)
C7'E	0.017 (2)	0.018 (2)	0.034 (2)	−0.0005 (16)	−0.0011 (16)	−0.0025 (16)
C8'E	0.020 (2)	0.019 (2)	0.052 (3)	0.0023 (17)	0.0013 (18)	0.0052 (18)
C9'E	0.027 (3)	0.025 (2)	0.073 (3)	0.0040 (19)	−0.005 (2)	0.004 (2)
N1'F	0.0164 (18)	0.0151 (17)	0.0324 (16)	−0.0065 (13)	−0.0001 (13)	−0.0023 (12)
C2'F	0.017 (2)	0.019 (2)	0.0258 (18)	−0.0025 (16)	0.0024 (15)	0.0003 (15)
N3'F	0.0192 (19)	0.0116 (16)	0.0324 (16)	0.0016 (13)	0.0000 (14)	−0.0034 (13)
C4'F	0.022 (2)	0.024 (2)	0.0250 (18)	0.0008 (18)	0.0010 (16)	0.0021 (16)
C5'F	0.015 (2)	0.021 (2)	0.031 (2)	0.0016 (16)	−0.0012 (15)	0.0013 (15)
C6'F	0.017 (2)	0.019 (2)	0.0235 (17)	0.0006 (16)	0.0008 (14)	−0.0009 (14)
S2'F	0.0174 (5)	0.0200 (5)	0.0463 (6)	0.0009 (4)	−0.0013 (4)	−0.0008 (4)
O4'F	0.0193 (17)	0.0195 (15)	0.0505 (17)	−0.0068 (12)	−0.0074 (13)	0.0011 (12)
C7'F	0.022 (2)	0.019 (2)	0.036 (2)	−0.0023 (16)	0.0029 (17)	−0.0017 (15)
C8'F	0.022 (2)	0.023 (2)	0.052 (3)	0.0013 (17)	−0.0007 (18)	−0.0023 (19)
C9'F	0.032 (3)	0.020 (2)	0.076 (3)	−0.0010 (19)	0.011 (2)	−0.007 (2)

Geometric parameters (Å, º)

N1A—C6A	1.330 (5)	N3'B—C4'B	1.398 (6)
N1A—C2A	1.350 (5)	N3'B—H3'B	0.8800
C2A—C3A	1.393 (6)	C4'B—O4'B	1.243 (5)
C2A—N21A	1.409 (5)	C4'B—C5'B	1.425 (6)
C3A—C4A	1.369 (6)	C5'B—C6'B	1.348 (6)
C3A—H3A	0.9500	C5'B—H5'B	0.9500
C4A—C5A	1.379 (6)	C6'B—C7'B	1.494 (5)
C4A—H4A	0.9500	C7'B—C8'B	1.530 (6)
C5A—C6A	1.406 (6)	C7'B—H7'3	0.9900
C5A—H5A	0.9500	C7'B—H7'4	0.9900
C6A—N61A	1.408 (5)	C8'B—C9'B	1.541 (6)
N21A—C22A	1.363 (5)	C8'B—H8'3	0.9900
N21A—H21A	0.8800	C8'B—H8'4	0.9900
C22A—O24A	1.253 (5)	C9'B—H9'4	0.9800
C22A—C23A	1.497 (6)	C9'B—H9'5	0.9800
C23A—H23A	0.9800	C9'B—H9'6	0.9800
C23A—H23B	0.9800	N1'C—C2'C	1.362 (5)
C23A—H23C	0.9800	N1'C—C6'C	1.389 (5)
N61A—C62A	1.369 (5)	N1'C—H1'C	0.8800
N61A—H61A	0.8800	C2'C—N3'C	1.362 (5)
C62A—O64A	1.235 (5)	C2'C—S2'C	1.677 (4)
C62A—C63A	1.510 (6)	N3'C—C4'C	1.398 (5)
C63A—H63A	0.9800	N3'C—H3'C	0.8800
C63A—H63B	0.9800	C4'C—O4'C	1.233 (5)
C63A—H63C	0.9800	C4'C—C5'C	1.426 (5)
N1B—C2B	1.331 (5)	C5'C—C6'C	1.353 (6)
N1B—C6B	1.366 (5)	C5'C—H5'C	0.9500
C2B—C3B	1.390 (6)	C6'C—C7'C	1.505 (5)
C2B—N21B	1.421 (5)	C7'C—C8'C	1.522 (6)
C3B—C4B	1.380 (7)	C7'C—H7'5	0.9900
C3B—H3B	0.9500	C7'C—H7'6	0.9900
C4B—C5B	1.380 (6)	C8'C—C9'C	1.512 (6)
C4B—H4B	0.9500	C8'C—H8'5	0.9900
C5B—C6B	1.375 (6)	C8'C—H8'6	0.9900
C5B—H5B	0.9500	C9'C—H9'7	0.9800
C6B—N61B	1.416 (5)	C9'C—H9'8	0.9800
N21B—C22B	1.376 (5)	C9'C—H9'9	0.9800
N21B—H21B	0.8800	N1'D—C2'D	1.355 (5)
C22B—O24B	1.222 (5)	N1'D—C6'D	1.390 (5)
C22B—C23B	1.519 (6)	N1'D—H1'D	0.8800
C23B—H23D	0.9800	C2'D—N3'D	1.367 (5)
C23B—H23E	0.9800	C2'D—S2'D	1.678 (4)
C23B—H23F	0.9800	N3'D—C4'D	1.403 (5)
N61B—C62B	1.372 (5)	N3'D—H3'D	0.8800
N61B—H61B	0.8800	C4'D—O4'D	1.236 (5)
C62B—O64B	1.224 (5)	C4'D—C5'D	1.435 (6)
C62B—C63B	1.503 (6)	C5'D—C6'D	1.353 (6)
C63B—H63D	0.9800	C5'D—H5'D	0.9500
C63B—H63E	0.9800	C6'D—C7'D	1.510 (5)
C63B—H63F	0.9800	C7'D—C8'D	1.506 (6)
N1C—C6C	1.343 (5)	C7'D—H7'7	0.9900
N1C—C2C	1.351 (5)	C7'D—H7'8	0.9900
C2C—C3C	1.374 (7)	C8'D—C9'D	1.534 (6)
C2C—N21C	1.416 (5)	C8'D—H8'7	0.9900
C3C—C4C	1.393 (7)	C8'D—H8'8	0.9900
C3C—H3C	0.9500	C9'D—H9'X	0.9800
C4C—C5C	1.360 (7)	C9'D—H9'Y	0.9800
C4C—H4C	0.9500	C9'D—H9'Z	0.9800
C5C—C6C	1.398 (6)	N1'E—C2'E	1.357 (5)
C5C—H5C	0.9500	N1'E—C6'E	1.394 (5)
C6C—N61C	1.402 (5)	N1'E—H1'E	0.8800
N21C—C22C	1.366 (5)	C2'E—N3'E	1.360 (6)
N21C—H21C	0.8800	C2'E—S2'E	1.673 (5)
C22C—O24C	1.244 (5)	N3'E—C4'E	1.396 (6)
C22C—C23C	1.503 (6)	N3'E—H3'E	0.8800
C23C—H23G	0.9800	C4'E—O4'E	1.231 (5)
C23C—H23H	0.9800	C4'E—C5'E	1.447 (6)
C23C—H23I	0.9800	C5'E—C6'E	1.352 (6)
N61C—C62C	1.370 (5)	C5'E—H5'E	0.9500
N61C—H61C	0.8800	C6'E—C7'E	1.499 (5)
C62C—O64C	1.225 (5)	C7'E—C8'E	1.536 (6)
C62C—C63C	1.515 (6)	C7'E—H7'9	0.9900
C63C—H63G	0.9800	C7'E—H7'X	0.9900
C63C—H63H	0.9800	C8'E—C9'E	1.543 (6)
C63C—H63I	0.9800	C8'E—H8'9	0.9900
N1'A—C2'A	1.362 (5)	C8'E—H8'X	0.9900
N1'A—C6'A	1.374 (5)	C9'E—H9'A	0.9800
N1'A—H1'A	0.8800	C9'E—H9'B	0.9800
C2'A—N3'A	1.365 (5)	C9'E—H9'C	0.9800
C2'A—S2'A	1.674 (4)	N1'F—C2'F	1.364 (5)
N3'A—C4'A	1.397 (5)	N1'F—C6'F	1.392 (5)
N3'A—H3'A	0.8800	N1'F—H1'F	0.8800
C4'A—O4'A	1.240 (5)	C2'F—N3'F	1.362 (5)
C4'A—C5'A	1.423 (6)	C2'F—S2'F	1.673 (4)
C5'A—C6'A	1.362 (6)	N3'F—C4'F	1.387 (5)
C5'A—H5'A	0.9500	N3'F—H3'F	0.8800
C6'A—C7'A	1.505 (5)	C4'F—O4'F	1.239 (5)
C7'A—C8'A	1.522 (6)	C4'F—C5'F	1.436 (5)
C7'A—H7'1	0.9900	C5'F—C6'F	1.360 (6)
C7'A—H7'2	0.9900	C5'F—H5'F	0.9500
C8'A—C9'A	1.523 (6)	C6'F—C7'F	1.490 (5)
C8'A—H8'1	0.9900	C7'F—C8'F	1.521 (6)
C8'A—H8'2	0.9900	C7'F—H7'Y	0.9900
C9'A—H9'1	0.9800	C7'F—H7'Z	0.9900
C9'A—H9'2	0.9800	C8'F—C9'F	1.525 (6)
C9'A—H9'3	0.9800	C8'F—H8'Y	0.9900
N1'B—C2'B	1.348 (5)	C8'F—H8'Z	0.9900
N1'B—C6'B	1.402 (5)	C9'F—H9'D	0.9800
N1'B—H1'B	0.8800	C9'F—H9'E	0.9800
C2'B—N3'B	1.363 (5)	C9'F—H9'F	0.9800
C2'B—S2'B	1.676 (4)
C6A—N1A—C2A	117.6 (3)	C6'B—C5'B—C4'B	120.8 (4)
N1A—C2A—C3A	123.2 (4)	C6'B—C5'B—H5'B	119.6
N1A—C2A—N21A	113.6 (4)	C4'B—C5'B—H5'B	119.6
C3A—C2A—N21A	123.2 (4)	C5'B—C6'B—N1'B	119.5 (4)
C4A—C3A—C2A	117.4 (4)	C5'B—C6'B—C7'B	126.2 (4)
C4A—C3A—H3A	121.3	N1'B—C6'B—C7'B	114.2 (4)
C2A—C3A—H3A	121.3	C6'B—C7'B—C8'B	114.8 (4)
C3A—C4A—C5A	121.5 (4)	C6'B—C7'B—H7'3	108.6
C3A—C4A—H4A	119.2	C8'B—C7'B—H7'3	108.6
C5A—C4A—H4A	119.2	C6'B—C7'B—H7'4	108.6
C4A—C5A—C6A	116.8 (4)	C8'B—C7'B—H7'4	108.6
C4A—C5A—H5A	121.6	H7'3—C7'B—H7'4	107.6
C6A—C5A—H5A	121.6	C7'B—C8'B—C9'B	111.1 (4)
N1A—C6A—C5A	123.5 (4)	C7'B—C8'B—H8'3	109.4
N1A—C6A—N61A	114.3 (4)	C9'B—C8'B—H8'3	109.4
C5A—C6A—N61A	122.1 (4)	C7'B—C8'B—H8'4	109.4
C22A—N21A—C2A	127.9 (4)	C9'B—C8'B—H8'4	109.4
C22A—N21A—H21A	116.1	H8'3—C8'B—H8'4	108.0
C2A—N21A—H21A	116.1	C8'B—C9'B—H9'4	109.5
O24A—C22A—N21A	122.4 (4)	C8'B—C9'B—H9'5	109.5
O24A—C22A—C23A	121.1 (4)	H9'4—C9'B—H9'5	109.5
N21A—C22A—C23A	116.5 (4)	C8'B—C9'B—H9'6	109.5
C22A—C23A—H23A	109.5	H9'4—C9'B—H9'6	109.5
C22A—C23A—H23B	109.5	H9'5—C9'B—H9'6	109.5
H23A—C23A—H23B	109.5	C2'C—N1'C—C6'C	123.4 (3)
C22A—C23A—H23C	109.5	C2'C—N1'C—H1'C	118.3
H23A—C23A—H23C	109.5	C6'C—N1'C—H1'C	118.3
H23B—C23A—H23C	109.5	N1'C—C2'C—N3'C	115.2 (4)
C62A—N61A—C6A	127.8 (4)	N1'C—C2'C—S2'C	122.6 (3)
C62A—N61A—H61A	116.1	N3'C—C2'C—S2'C	122.3 (3)
C6A—N61A—H61A	116.1	C2'C—N3'C—C4'C	126.1 (3)
O64A—C62A—N61A	122.3 (4)	C2'C—N3'C—H3'C	116.9
O64A—C62A—C63A	121.6 (4)	C4'C—N3'C—H3'C	116.9
N61A—C62A—C63A	116.1 (4)	O4'C—C4'C—N3'C	118.4 (4)
C62A—C63A—H63A	109.5	O4'C—C4'C—C5'C	126.8 (4)
C62A—C63A—H63B	109.5	N3'C—C4'C—C5'C	114.9 (4)
H63A—C63A—H63B	109.5	C6'C—C5'C—C4'C	120.7 (4)
C62A—C63A—H63C	109.5	C6'C—C5'C—H5'C	119.6
H63A—C63A—H63C	109.5	C4'C—C5'C—H5'C	119.6
H63B—C63A—H63C	109.5	C5'C—C6'C—N1'C	119.6 (3)
C2B—N1B—C6B	116.7 (4)	C5'C—C6'C—C7'C	125.8 (4)
N1B—C2B—C3B	124.2 (4)	N1'C—C6'C—C7'C	114.7 (4)
N1B—C2B—N21B	113.7 (4)	C6'C—C7'C—C8'C	114.7 (4)
C3B—C2B—N21B	122.1 (4)	C6'C—C7'C—H7'5	108.6
C4B—C3B—C2B	117.0 (4)	C8'C—C7'C—H7'5	108.6
C4B—C3B—H3B	121.5	C6'C—C7'C—H7'6	108.6
C2B—C3B—H3B	121.5	C8'C—C7'C—H7'6	108.6
C5B—C4B—C3B	121.0 (5)	H7'5—C7'C—H7'6	107.6
C5B—C4B—H4B	119.5	C9'C—C8'C—C7'C	110.9 (4)
C3B—C4B—H4B	119.5	C9'C—C8'C—H8'5	109.5
C6B—C5B—C4B	117.6 (4)	C7'C—C8'C—H8'5	109.5
C6B—C5B—H5B	121.2	C9'C—C8'C—H8'6	109.5
C4B—C5B—H5B	121.2	C7'C—C8'C—H8'6	109.5
N1B—C6B—C5B	123.4 (4)	H8'5—C8'C—H8'6	108.0
N1B—C6B—N61B	113.2 (4)	C8'C—C9'C—H9'7	109.5
C5B—C6B—N61B	123.4 (4)	C8'C—C9'C—H9'8	109.5
C22B—N21B—C2B	126.9 (4)	H9'7—C9'C—H9'8	109.5
C22B—N21B—H21B	116.6	C8'C—C9'C—H9'9	109.5
C2B—N21B—H21B	116.6	H9'7—C9'C—H9'9	109.5
O24B—C22B—N21B	124.2 (4)	H9'8—C9'C—H9'9	109.5
O24B—C22B—C23B	121.3 (4)	C2'D—N1'D—C6'D	123.5 (3)
N21B—C22B—C23B	114.5 (4)	C2'D—N1'D—H1'D	118.3
C22B—C23B—H23D	109.5	C6'D—N1'D—H1'D	118.3
C22B—C23B—H23E	109.5	N1'D—C2'D—N3'D	115.5 (3)
H23D—C23B—H23E	109.5	N1'D—C2'D—S2'D	122.0 (3)
C22B—C23B—H23F	109.5	N3'D—C2'D—S2'D	122.6 (3)
H23D—C23B—H23F	109.5	C2'D—N3'D—C4'D	126.0 (3)
H23E—C23B—H23F	109.5	C2'D—N3'D—H3'D	117.0
C62B—N61B—C6B	126.6 (4)	C4'D—N3'D—H3'D	117.0
C62B—N61B—H61B	116.7	O4'D—C4'D—N3'D	118.1 (4)
C6B—N61B—H61B	116.7	O4'D—C4'D—C5'D	127.3 (4)
O64B—C62B—N61B	122.9 (4)	N3'D—C4'D—C5'D	114.6 (4)
O64B—C62B—C63B	121.9 (4)	C6'D—C5'D—C4'D	120.7 (4)
N61B—C62B—C63B	115.2 (4)	C6'D—C5'D—H5'D	119.7
C62B—C63B—H63D	109.5	C4'D—C5'D—H5'D	119.7
C62B—C63B—H63E	109.5	C5'D—C6'D—N1'D	119.8 (4)
H63D—C63B—H63E	109.5	C5'D—C6'D—C7'D	125.9 (4)
C62B—C63B—H63F	109.5	N1'D—C6'D—C7'D	114.3 (3)
H63D—C63B—H63F	109.5	C8'D—C7'D—C6'D	116.5 (4)
H63E—C63B—H63F	109.5	C8'D—C7'D—H7'7	108.2
C6C—N1C—C2C	117.8 (3)	C6'D—C7'D—H7'7	108.2
N1C—C2C—C3C	123.2 (4)	C8'D—C7'D—H7'8	108.2
N1C—C2C—N21C	114.2 (4)	C6'D—C7'D—H7'8	108.2
C3C—C2C—N21C	122.6 (4)	H7'7—C7'D—H7'8	107.3
C2C—C3C—C4C	117.5 (4)	C7'D—C8'D—C9'D	110.6 (4)
C2C—C3C—H3C	121.3	C7'D—C8'D—H8'7	109.5
C4C—C3C—H3C	121.3	C9'D—C8'D—H8'7	109.5
C5C—C4C—C3C	121.0 (4)	C7'D—C8'D—H8'8	109.5
C5C—C4C—H4C	119.5	C9'D—C8'D—H8'8	109.5
C3C—C4C—H4C	119.5	H8'7—C8'D—H8'8	108.1
C4C—C5C—C6C	117.8 (4)	C8'D—C9'D—H9'X	109.5
C4C—C5C—H5C	121.1	C8'D—C9'D—H9'Y	109.5
C6C—C5C—H5C	121.1	H9'X—C9'D—H9'Y	109.5
N1C—C6C—C5C	122.7 (4)	C8'D—C9'D—H9'Z	109.5
N1C—C6C—N61C	114.9 (4)	H9'X—C9'D—H9'Z	109.5
C5C—C6C—N61C	122.4 (4)	H9'Y—C9'D—H9'Z	109.5
C22C—N21C—C2C	127.5 (4)	C2'E—N1'E—C6'E	123.7 (4)
C22C—N21C—H21C	116.3	C2'E—N1'E—H1'E	118.1
C2C—N21C—H21C	116.3	C6'E—N1'E—H1'E	118.1
O24C—C22C—N21C	123.2 (4)	N1'E—C2'E—N3'E	115.2 (4)
O24C—C22C—C23C	120.4 (4)	N1'E—C2'E—S2'E	121.8 (3)
N21C—C22C—C23C	116.4 (4)	N3'E—C2'E—S2'E	123.0 (3)
C22C—C23C—H23G	109.5	C2'E—N3'E—C4'E	126.5 (3)
C22C—C23C—H23H	109.5	C2'E—N3'E—H3'E	116.7
H23G—C23C—H23H	109.5	C4'E—N3'E—H3'E	116.7
C22C—C23C—H23I	109.5	O4'E—C4'E—N3'E	119.1 (4)
H23G—C23C—H23I	109.5	O4'E—C4'E—C5'E	126.4 (4)
H23H—C23C—H23I	109.5	N3'E—C4'E—C5'E	114.5 (4)
C62C—N61C—C6C	127.6 (4)	C6'E—C5'E—C4'E	120.4 (4)
C62C—N61C—H61C	116.2	C6'E—C5'E—H5'E	119.8
C6C—N61C—H61C	116.2	C4'E—C5'E—H5'E	119.8
O64C—C62C—N61C	123.5 (4)	C5'E—C6'E—N1'E	119.5 (4)
O64C—C62C—C63C	120.3 (4)	C5'E—C6'E—C7'E	126.3 (4)
N61C—C62C—C63C	116.2 (4)	N1'E—C6'E—C7'E	114.2 (4)
C62C—C63C—H63G	109.5	C6'E—C7'E—C8'E	114.8 (4)
C62C—C63C—H63H	109.5	C6'E—C7'E—H7'9	108.6
H63G—C63C—H63H	109.5	C8'E—C7'E—H7'9	108.6
C62C—C63C—H63I	109.5	C6'E—C7'E—H7'X	108.6
H63G—C63C—H63I	109.5	C8'E—C7'E—H7'X	108.6
H63H—C63C—H63I	109.5	H7'9—C7'E—H7'X	107.5
C2'A—N1'A—C6'A	124.2 (3)	C7'E—C8'E—C9'E	109.6 (4)
C2'A—N1'A—H1'A	117.9	C7'E—C8'E—H8'9	109.8
C6'A—N1'A—H1'A	117.9	C9'E—C8'E—H8'9	109.8
N1'A—C2'A—N3'A	114.3 (4)	C7'E—C8'E—H8'X	109.8
N1'A—C2'A—S2'A	122.8 (3)	C9'E—C8'E—H8'X	109.8
N3'A—C2'A—S2'A	122.9 (3)	H8'9—C8'E—H8'X	108.2
C2'A—N3'A—C4'A	126.6 (3)	C8'E—C9'E—H9'A	109.5
C2'A—N3'A—H3'A	116.7	C8'E—C9'E—H9'B	109.5
C4'A—N3'A—H3'A	116.7	H9'A—C9'E—H9'B	109.5
O4'A—C4'A—N3'A	118.1 (4)	C8'E—C9'E—H9'C	109.5
O4'A—C4'A—C5'A	127.2 (4)	H9'A—C9'E—H9'C	109.5
N3'A—C4'A—C5'A	114.8 (4)	H9'B—C9'E—H9'C	109.5
C6'A—C5'A—C4'A	120.4 (4)	C2'F—N1'F—C6'F	123.6 (3)
C6'A—C5'A—H5'A	119.8	C2'F—N1'F—H1'F	118.2
C4'A—C5'A—H5'A	119.8	C6'F—N1'F—H1'F	118.2
C5'A—C6'A—N1'A	119.6 (4)	N3'F—C2'F—N1'F	115.0 (4)
C5'A—C6'A—C7'A	125.3 (4)	N3'F—C2'F—S2'F	122.9 (3)
N1'A—C6'A—C7'A	115.1 (3)	N1'F—C2'F—S2'F	122.1 (3)
C6'A—C7'A—C8'A	115.4 (3)	C2'F—N3'F—C4'F	126.6 (3)
C6'A—C7'A—H7'1	108.4	C2'F—N3'F—H3'F	116.7
C8'A—C7'A—H7'1	108.4	C4'F—N3'F—H3'F	116.7
C6'A—C7'A—H7'2	108.4	O4'F—C4'F—N3'F	119.2 (4)
C8'A—C7'A—H7'2	108.4	O4'F—C4'F—C5'F	125.8 (4)
H7'1—C7'A—H7'2	107.5	N3'F—C4'F—C5'F	115.0 (4)
C7'A—C8'A—C9'A	110.9 (3)	C6'F—C5'F—C4'F	120.3 (4)
C7'A—C8'A—H8'1	109.5	C6'F—C5'F—H5'F	119.8
C9'A—C8'A—H8'1	109.5	C4'F—C5'F—H5'F	119.8
C7'A—C8'A—H8'2	109.5	C5'F—C6'F—N1'F	119.4 (4)
C9'A—C8'A—H8'2	109.5	C5'F—C6'F—C7'F	125.8 (4)
H8'1—C8'A—H8'2	108.0	N1'F—C6'F—C7'F	114.8 (4)
C8'A—C9'A—H9'1	109.5	C6'F—C7'F—C8'F	116.0 (4)
C8'A—C9'A—H9'2	109.5	C6'F—C7'F—H7'Y	108.3
H9'1—C9'A—H9'2	109.5	C8'F—C7'F—H7'Y	108.3
C8'A—C9'A—H9'3	109.5	C6'F—C7'F—H7'Z	108.3
H9'1—C9'A—H9'3	109.5	C8'F—C7'F—H7'Z	108.3
H9'2—C9'A—H9'3	109.5	H7'Y—C7'F—H7'Z	107.4
C2'B—N1'B—C6'B	123.3 (4)	C7'F—C8'F—C9'F	111.2 (4)
C2'B—N1'B—H1'B	118.4	C7'F—C8'F—H8'Y	109.4
C6'B—N1'B—H1'B	118.4	C9'F—C8'F—H8'Y	109.4
N1'B—C2'B—N3'B	115.4 (4)	C7'F—C8'F—H8'Z	109.4
N1'B—C2'B—S2'B	123.1 (3)	C9'F—C8'F—H8'Z	109.4
N3'B—C2'B—S2'B	121.5 (3)	H8'Y—C8'F—H8'Z	108.0
C2'B—N3'B—C4'B	126.2 (3)	C8'F—C9'F—H9'D	109.5
C2'B—N3'B—H3'B	116.9	C8'F—C9'F—H9'E	109.5
C4'B—N3'B—H3'B	116.9	H9'D—C9'F—H9'E	109.5
O4'B—C4'B—N3'B	118.4 (4)	C8'F—C9'F—H9'F	109.5
O4'B—C4'B—C5'B	126.8 (4)	H9'D—C9'F—H9'F	109.5
N3'B—C4'B—C5'B	114.7 (4)	H9'E—C9'F—H9'F	109.5
C6A—N1A—C2A—C3A	0.7 (6)	S2'B—C2'B—N3'B—C4'B	−174.8 (3)
C6A—N1A—C2A—N21A	−178.6 (3)	C2'B—N3'B—C4'B—O4'B	175.3 (3)
N1A—C2A—C3A—C4A	0.3 (6)	C2'B—N3'B—C4'B—C5'B	−3.7 (5)
N21A—C2A—C3A—C4A	179.5 (4)	O4'B—C4'B—C5'B—C6'B	−177.7 (4)
C2A—C3A—C4A—C5A	−0.8 (7)	N3'B—C4'B—C5'B—C6'B	1.3 (5)
C3A—C4A—C5A—C6A	0.3 (7)	C4'B—C5'B—C6'B—N1'B	1.4 (6)
C2A—N1A—C6A—C5A	−1.2 (6)	C4'B—C5'B—C6'B—C7'B	−180.0 (3)
C2A—N1A—C6A—N61A	−179.0 (3)	C2'B—N1'B—C6'B—C5'B	−2.2 (5)
C4A—C5A—C6A—N1A	0.8 (6)	C2'B—N1'B—C6'B—C7'B	179.1 (3)
C4A—C5A—C6A—N61A	178.4 (4)	C5'B—C6'B—C7'B—C8'B	3.1 (6)
N1A—C2A—N21A—C22A	−167.1 (4)	N1'B—C6'B—C7'B—C8'B	−178.2 (3)
C3A—C2A—N21A—C22A	13.7 (6)	C6'B—C7'B—C8'B—C9'B	178.8 (3)
C2A—N21A—C22A—O24A	0.9 (6)	C6'C—N1'C—C2'C—N3'C	0.8 (5)
C2A—N21A—C22A—C23A	179.9 (3)	C6'C—N1'C—C2'C—S2'C	−178.2 (3)
N1A—C6A—N61A—C62A	−166.1 (4)	N1'C—C2'C—N3'C—C4'C	−3.3 (5)
C5A—C6A—N61A—C62A	16.1 (6)	S2'C—C2'C—N3'C—C4'C	175.7 (3)
C6A—N61A—C62A—O64A	1.2 (6)	C2'C—N3'C—C4'C—O4'C	−176.8 (3)
C6A—N61A—C62A—C63A	178.5 (4)	C2'C—N3'C—C4'C—C5'C	4.4 (5)
C6B—N1B—C2B—C3B	−0.2 (6)	O4'C—C4'C—C5'C—C6'C	178.1 (4)
C6B—N1B—C2B—N21B	179.3 (3)	N3'C—C4'C—C5'C—C6'C	−3.1 (5)
N1B—C2B—C3B—C4B	0.1 (6)	C4'C—C5'C—C6'C—N1'C	1.1 (5)
N21B—C2B—C3B—C4B	−179.4 (4)	C4'C—C5'C—C6'C—C7'C	−177.8 (3)
C2B—C3B—C4B—C5B	−0.6 (7)	C2'C—N1'C—C6'C—C5'C	0.1 (5)
C3B—C4B—C5B—C6B	1.2 (7)	C2'C—N1'C—C6'C—C7'C	179.2 (3)
C2B—N1B—C6B—C5B	0.8 (6)	C5'C—C6'C—C7'C—C8'C	−4.2 (5)
C2B—N1B—C6B—N61B	179.8 (3)	N1'C—C6'C—C7'C—C8'C	176.9 (3)
C4B—C5B—C6B—N1B	−1.3 (6)	C6'C—C7'C—C8'C—C9'C	178.1 (3)
C4B—C5B—C6B—N61B	179.8 (4)	C6'D—N1'D—C2'D—N3'D	0.8 (5)
N1B—C2B—N21B—C22B	167.9 (3)	C6'D—N1'D—C2'D—S2'D	−179.1 (3)
C3B—C2B—N21B—C22B	−12.6 (6)	N1'D—C2'D—N3'D—C4'D	0.5 (5)
C2B—N21B—C22B—O24B	−0.5 (6)	S2'D—C2'D—N3'D—C4'D	−179.6 (3)
C2B—N21B—C22B—C23B	179.7 (3)	C2'D—N3'D—C4'D—O4'D	179.4 (4)
N1B—C6B—N61B—C62B	166.5 (3)	C2'D—N3'D—C4'D—C5'D	−1.3 (5)
C5B—C6B—N61B—C62B	−14.5 (6)	O4'D—C4'D—C5'D—C6'D	−179.9 (4)
C6B—N61B—C62B—O64B	−1.3 (6)	N3'D—C4'D—C5'D—C6'D	0.9 (5)
C6B—N61B—C62B—C63B	179.1 (4)	C4'D—C5'D—C6'D—N1'D	0.3 (5)
C6C—N1C—C2C—C3C	−0.2 (6)	C4'D—C5'D—C6'D—C7'D	−179.5 (3)
C6C—N1C—C2C—N21C	−179.4 (3)	C2'D—N1'D—C6'D—C5'D	−1.2 (5)
N1C—C2C—C3C—C4C	1.0 (7)	C2'D—N1'D—C6'D—C7'D	178.6 (3)
N21C—C2C—C3C—C4C	−179.9 (4)	C5'D—C6'D—C7'D—C8'D	−3.5 (6)
C2C—C3C—C4C—C5C	−1.8 (8)	N1'D—C6'D—C7'D—C8'D	176.7 (3)
C3C—C4C—C5C—C6C	1.8 (8)	C6'D—C7'D—C8'D—C9'D	178.0 (3)
C2C—N1C—C6C—C5C	0.2 (6)	C6'E—N1'E—C2'E—N3'E	−1.9 (5)
C2C—N1C—C6C—N61C	−178.8 (3)	C6'E—N1'E—C2'E—S2'E	179.3 (3)
C4C—C5C—C6C—N1C	−1.0 (7)	N1'E—C2'E—N3'E—C4'E	1.6 (6)
C4C—C5C—C6C—N61C	177.9 (4)	S2'E—C2'E—N3'E—C4'E	−179.5 (3)
N1C—C2C—N21C—C22C	−169.8 (4)	C2'E—N3'E—C4'E—O4'E	179.9 (4)
C3C—C2C—N21C—C22C	11.0 (6)	C2'E—N3'E—C4'E—C5'E	−0.8 (6)
C2C—N21C—C22C—O24C	3.6 (6)	O4'E—C4'E—C5'E—C6'E	179.3 (4)
C2C—N21C—C22C—C23C	−177.8 (4)	N3'E—C4'E—C5'E—C6'E	0.1 (6)
N1C—C6C—N61C—C62C	−167.2 (3)	C4'E—C5'E—C6'E—N1'E	−0.3 (6)
C5C—C6C—N61C—C62C	13.8 (6)	C4'E—C5'E—C6'E—C7'E	179.4 (3)
C6C—N61C—C62C—O64C	3.3 (6)	C2'E—N1'E—C6'E—C5'E	1.3 (5)
C6C—N61C—C62C—C63C	−177.9 (3)	C2'E—N1'E—C6'E—C7'E	−178.5 (3)
C6'A—N1'A—C2'A—N3'A	0.6 (5)	C5'E—C6'E—C7'E—C8'E	1.9 (6)
C6'A—N1'A—C2'A—S2'A	−178.8 (3)	N1'E—C6'E—C7'E—C8'E	−178.4 (3)
N1'A—C2'A—N3'A—C4'A	−3.0 (5)	C6'E—C7'E—C8'E—C9'E	−177.4 (3)
S2'A—C2'A—N3'A—C4'A	176.4 (3)	C6'F—N1'F—C2'F—N3'F	−0.2 (5)
C2'A—N3'A—C4'A—O4'A	−175.8 (3)	C6'F—N1'F—C2'F—S2'F	−179.7 (3)
C2'A—N3'A—C4'A—C5'A	3.5 (5)	N1'F—C2'F—N3'F—C4'F	0.6 (5)
O4'A—C4'A—C5'A—C6'A	177.7 (4)	S2'F—C2'F—N3'F—C4'F	−179.9 (3)
N3'A—C4'A—C5'A—C6'A	−1.5 (5)	C2'F—N3'F—C4'F—O4'F	178.3 (4)
C4'A—C5'A—C6'A—N1'A	−0.5 (5)	C2'F—N3'F—C4'F—C5'F	−0.4 (5)
C4'A—C5'A—C6'A—C7'A	179.4 (3)	O4'F—C4'F—C5'F—C6'F	−179.0 (4)
C2'A—N1'A—C6'A—C5'A	1.1 (5)	N3'F—C4'F—C5'F—C6'F	−0.3 (5)
C2'A—N1'A—C6'A—C7'A	−178.9 (3)	C4'F—C5'F—C6'F—N1'F	0.7 (5)
C5'A—C6'A—C7'A—C8'A	−1.3 (5)	C4'F—C5'F—C6'F—C7'F	179.6 (3)
N1'A—C6'A—C7'A—C8'A	178.7 (3)	C2'F—N1'F—C6'F—C5'F	−0.4 (5)
C6'A—C7'A—C8'A—C9'A	−178.2 (3)	C2'F—N1'F—C6'F—C7'F	−179.4 (3)
C6'B—N1'B—C2'B—N3'B	0.0 (5)	C5'F—C6'F—C7'F—C8'F	3.0 (5)
C6'B—N1'B—C2'B—S2'B	177.9 (3)	N1'F—C6'F—C7'F—C8'F	−178.0 (3)
N1'B—C2'B—N3'B—C4'B	3.1 (5)	C6'F—C7'F—C8'F—C9'F	179.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···O4′D^i	0.88	2.03	2.904 (5)	169
N61A—H61A···O4′E^ii	0.88	2.05	2.921 (5)	171
N21B—H21B···O4′A	0.88	2.04	2.906 (5)	170
N61B—H61B···O4′F^iii	0.88	2.03	2.893 (5)	169
N21C—H21C···O4′B	0.88	2.01	2.873 (5)	168
N61C—H61C···O4′C^iv	0.88	2.07	2.934 (5)	165
N1′A—H1′A···O24A	0.88	2.03	2.892 (4)	167
N3′A—H3′A···S2′D	0.88	2.42	3.279 (3)	166
N1′B—H1′B···O24B	0.88	2.00	2.859 (5)	165
N3′B—H3′B···S2′E	0.88	2.43	3.286 (4)	165
N1′C—H1′C···O24C	0.88	2.09	2.951 (4)	166
N3′C—H3′C···S2′F	0.88	2.45	3.313 (3)	166
N1′D—H1′D···O64A^v	0.88	2.00	2.870 (5)	168
N3′D—H3′D···S2′A	0.88	2.45	3.317 (3)	168
N1′E—H1′E···O64B^vi	0.88	2.06	2.919 (4)	166
N3′E—H3′E···S2′B	0.88	2.49	3.358 (3)	168
N1′F—H1′F···O64C^vii	0.88	2.08	2.944 (4)	166
N3′F—H3′F···S2′C	0.88	2.49	3.359 (3)	168

Symmetry codes: (i) −x, −y+1, z; (ii) −x+1/4, y−1/4, z−1/4; (iii) −x+3/4, y−1/4, z+1/4; (iv) x−1/4, −y+5/4, z−1/4; (v) −x+1/4, y+1/4, z+1/4; (vi) −x+3/4, y+1/4, z−1/4; (vii) −x+5/4, y+1/4, z+1/4.

(III) 6-propyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-4-one

Crystal data

C7H10N2OS	Dx = 1.356 Mg m^−3
Mr = 170.23	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9432 reflections
a = 10.4340 (6) Å	θ = 3.4–25.9°
b = 11.1320 (6) Å	µ = 0.33 mm^−1
c = 28.7090 (17) Å	T = 173 K
V = 3334.6 (3) Å^3	Block, colourless
Z = 16	0.40 × 0.20 × 0.20 mm
F(000) = 1440

Data collection

Stoe IPDS II two-circle diffractometer	3131 independent reflections
Radiation source: fine-focus sealed tube	1990 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.132
ω scans	θmax = 25.6°, θmin = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −12→12
Tmin = 0.879, Tmax = 0.937	k = −13→13
29872 measured reflections	l = −31→34

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0362P)^2] where P = (Fo^2 + 2Fc^2)/3
3131 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

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

	x	y	z	Uiso*/Ueq
N1A	0.8859 (2)	0.2776 (2)	0.57732 (8)	0.0214 (5)
H1A	0.8838	0.1990	0.5806	0.026*
C2A	0.9065 (3)	0.3450 (2)	0.61574 (9)	0.0181 (6)
S2A	0.92485 (8)	0.28630 (6)	0.66912 (2)	0.02394 (17)
N3A	0.9118 (2)	0.46603 (19)	0.60853 (8)	0.0206 (5)
H3A	0.9252	0.5120	0.6330	0.025*
C4A	0.8978 (3)	0.5223 (2)	0.56577 (10)	0.0212 (6)
O4A	0.9048 (2)	0.63362 (16)	0.56353 (7)	0.0288 (5)
C5A	0.8741 (3)	0.4450 (2)	0.52715 (11)	0.0230 (6)
H5A	0.8625	0.4781	0.4969	0.028*
C6A	0.8680 (3)	0.3243 (2)	0.53336 (10)	0.0196 (6)
C7A	0.8417 (3)	0.2344 (3)	0.49555 (11)	0.0242 (7)
H7A1	0.7952	0.1654	0.5093	0.029*
H7A2	0.9246	0.2040	0.4836	0.029*
C8A	0.7643 (3)	0.2822 (3)	0.45478 (13)	0.0349 (8)
H8A1	0.6842	0.3189	0.4667	0.042*
H8A2	0.8140	0.3458	0.4389	0.042*
C9A	0.7306 (3)	0.1846 (3)	0.41987 (13)	0.0337 (8)
H9A1	0.8095	0.1474	0.4082	0.050*
H9A2	0.6833	0.2201	0.3938	0.050*
H9A3	0.6774	0.1236	0.4350	0.050*
N1B	0.8939 (2)	0.98578 (19)	0.67050 (8)	0.0215 (5)
H1B	0.8903	1.0644	0.6675	0.026*
C2B	0.9147 (3)	0.9196 (2)	0.63148 (10)	0.0209 (6)
S2B	0.93405 (8)	0.98091 (6)	0.57878 (3)	0.02508 (19)
N3B	0.9176 (2)	0.79850 (19)	0.63823 (8)	0.0205 (5)
H3B	0.9312	0.7531	0.6136	0.025*
C4B	0.9008 (3)	0.7404 (2)	0.68095 (11)	0.0239 (7)
O4B	0.9026 (2)	0.62950 (17)	0.68242 (7)	0.0300 (5)
C5B	0.8849 (3)	0.8183 (3)	0.72011 (10)	0.0244 (6)
H5B	0.8791	0.7849	0.7505	0.029*
C6B	0.8780 (3)	0.9383 (3)	0.71454 (10)	0.0221 (6)
C7B	0.8538 (3)	1.0276 (3)	0.75279 (12)	0.0303 (7)
H7B1	0.8129	1.0996	0.7391	0.036*
H7B2	0.9374	1.0529	0.7659	0.036*
C8B	0.7705 (4)	0.9829 (3)	0.79208 (15)	0.0402 (9)
H8B1	0.8120	0.9123	0.8067	0.048*
H8B2	0.6871	0.9565	0.7793	0.048*
C9B	0.7475 (3)	1.0777 (3)	0.82892 (14)	0.0383 (8)
H9B1	0.8299	1.1075	0.8405	0.057*
H9B2	0.6987	1.0427	0.8547	0.057*
H9B3	0.6989	1.1444	0.8154	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0306 (13)	0.0130 (10)	0.0205 (13)	−0.0002 (9)	−0.0014 (10)	−0.0006 (11)
C2A	0.0181 (14)	0.0156 (13)	0.0205 (14)	0.0002 (11)	0.0011 (11)	−0.0007 (11)
S2A	0.0348 (4)	0.0190 (3)	0.0180 (3)	−0.0003 (3)	−0.0025 (3)	0.0004 (3)
N3A	0.0266 (13)	0.0146 (11)	0.0207 (13)	−0.0019 (10)	−0.0020 (11)	−0.0022 (9)
C4A	0.0268 (16)	0.0147 (13)	0.0220 (15)	0.0010 (11)	0.0030 (12)	−0.0021 (12)
O4A	0.0481 (13)	0.0141 (9)	0.0241 (10)	−0.0006 (9)	0.0010 (10)	−0.0008 (8)
C5A	0.0312 (16)	0.0192 (14)	0.0186 (15)	−0.0014 (12)	0.0009 (12)	0.0013 (12)
C6A	0.0211 (14)	0.0179 (13)	0.0196 (15)	0.0007 (11)	0.0012 (11)	0.0024 (12)
C7A	0.0349 (17)	0.0168 (15)	0.0210 (16)	−0.0018 (12)	−0.0001 (12)	−0.0028 (12)
C8A	0.046 (2)	0.0318 (17)	0.027 (2)	0.0062 (16)	−0.0132 (14)	−0.0023 (16)
C9A	0.0393 (18)	0.0331 (17)	0.029 (2)	−0.0054 (14)	−0.0051 (14)	0.0012 (15)
N1B	0.0322 (14)	0.0135 (11)	0.0189 (13)	0.0006 (9)	−0.0005 (10)	−0.0008 (10)
C2B	0.0204 (14)	0.0195 (13)	0.0227 (15)	0.0000 (12)	−0.0027 (12)	−0.0031 (11)
S2B	0.0378 (4)	0.0177 (3)	0.0197 (4)	0.0041 (3)	0.0017 (3)	0.0002 (3)
N3B	0.0289 (13)	0.0130 (11)	0.0196 (12)	0.0017 (10)	0.0007 (11)	−0.0027 (9)
C4B	0.0224 (16)	0.0222 (15)	0.0270 (17)	0.0005 (11)	−0.0027 (13)	0.0007 (11)
O4B	0.0490 (14)	0.0135 (10)	0.0275 (11)	0.0024 (9)	0.0004 (10)	0.0021 (8)
C5B	0.0343 (17)	0.0211 (14)	0.0178 (15)	−0.0033 (12)	−0.0037 (12)	0.0010 (12)
C6B	0.0249 (15)	0.0219 (15)	0.0195 (16)	−0.0028 (12)	−0.0043 (12)	−0.0035 (12)
C7B	0.050 (2)	0.0196 (14)	0.0209 (16)	0.0004 (13)	−0.0001 (14)	−0.0072 (14)
C8B	0.047 (2)	0.0318 (18)	0.041 (2)	−0.0016 (16)	0.0135 (17)	−0.0075 (17)
C9B	0.049 (2)	0.0366 (17)	0.030 (2)	0.0089 (15)	0.0075 (15)	−0.0035 (17)

Geometric parameters (Å, º)

N1A—C2A	1.351 (4)	N1B—C2B	1.358 (4)
N1A—C6A	1.378 (4)	N1B—C6B	1.380 (4)
N1A—H1A	0.8800	N1B—H1B	0.8800
C2A—N3A	1.364 (3)	C2B—N3B	1.363 (3)
C2A—S2A	1.677 (3)	C2B—S2B	1.672 (3)
N3A—C4A	1.386 (4)	N3B—C4B	1.397 (4)
N3A—H3A	0.8800	N3B—H3B	0.8800
C4A—O4A	1.243 (3)	C4B—O4B	1.236 (3)
C4A—C5A	1.425 (4)	C4B—C5B	1.429 (4)
C5A—C6A	1.357 (4)	C5B—C6B	1.348 (4)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—C7A	1.502 (4)	C6B—C7B	1.503 (4)
C7A—C8A	1.519 (5)	C7B—C8B	1.508 (5)
C7A—H7A1	0.9900	C7B—H7B1	0.9900
C7A—H7A2	0.9900	C7B—H7B2	0.9900
C8A—C9A	1.519 (5)	C8B—C9B	1.514 (5)
C8A—H8A1	0.9900	C8B—H8B1	0.9900
C8A—H8A2	0.9900	C8B—H8B2	0.9900
C9A—H9A1	0.9800	C9B—H9B1	0.9800
C9A—H9A2	0.9800	C9B—H9B2	0.9800
C9A—H9A3	0.9800	C9B—H9B3	0.9800
C2A—N1A—C6A	124.0 (2)	C2B—N1B—C6B	124.6 (2)
C2A—N1A—H1A	118.0	C2B—N1B—H1B	117.7
C6A—N1A—H1A	118.0	C6B—N1B—H1B	117.7
N1A—C2A—N3A	115.5 (2)	N1B—C2B—N3B	115.0 (3)
N1A—C2A—S2A	123.2 (2)	N1B—C2B—S2B	123.0 (2)
N3A—C2A—S2A	121.3 (2)	N3B—C2B—S2B	122.0 (2)
C2A—N3A—C4A	125.2 (2)	C2B—N3B—C4B	125.4 (2)
C2A—N3A—H3A	117.4	C2B—N3B—H3B	117.3
C4A—N3A—H3A	117.4	C4B—N3B—H3B	117.3
O4A—C4A—N3A	119.4 (3)	O4B—C4B—N3B	119.4 (3)
O4A—C4A—C5A	124.9 (3)	O4B—C4B—C5B	125.5 (3)
N3A—C4A—C5A	115.7 (2)	N3B—C4B—C5B	115.1 (2)
C6A—C5A—C4A	120.3 (3)	C6B—C5B—C4B	120.9 (3)
C6A—C5A—H5A	119.9	C6B—C5B—H5B	119.5
C4A—C5A—H5A	119.9	C4B—C5B—H5B	119.5
C5A—C6A—N1A	119.2 (3)	C5B—C6B—N1B	118.8 (3)
C5A—C6A—C7A	125.0 (3)	C5B—C6B—C7B	125.3 (3)
N1A—C6A—C7A	115.8 (2)	N1B—C6B—C7B	115.9 (2)
C6A—C7A—C8A	114.9 (2)	C6B—C7B—C8B	115.2 (3)
C6A—C7A—H7A1	108.6	C6B—C7B—H7B1	108.5
C8A—C7A—H7A1	108.6	C8B—C7B—H7B1	108.5
C6A—C7A—H7A2	108.6	C6B—C7B—H7B2	108.5
C8A—C7A—H7A2	108.6	C8B—C7B—H7B2	108.5
H7A1—C7A—H7A2	107.5	H7B1—C7B—H7B2	107.5
C9A—C8A—C7A	112.4 (3)	C7B—C8B—C9B	112.6 (3)
C9A—C8A—H8A1	109.1	C7B—C8B—H8B1	109.1
C7A—C8A—H8A1	109.1	C9B—C8B—H8B1	109.1
C9A—C8A—H8A2	109.1	C7B—C8B—H8B2	109.1
C7A—C8A—H8A2	109.1	C9B—C8B—H8B2	109.1
H8A1—C8A—H8A2	107.9	H8B1—C8B—H8B2	107.8
C8A—C9A—H9A1	109.5	C8B—C9B—H9B1	109.5
C8A—C9A—H9A2	109.5	C8B—C9B—H9B2	109.5
H9A1—C9A—H9A2	109.5	H9B1—C9B—H9B2	109.5
C8A—C9A—H9A3	109.5	C8B—C9B—H9B3	109.5
H9A1—C9A—H9A3	109.5	H9B1—C9B—H9B3	109.5
H9A2—C9A—H9A3	109.5	H9B2—C9B—H9B3	109.5
C6A—N1A—C2A—N3A	−1.5 (4)	C6B—N1B—C2B—N3B	0.8 (4)
C6A—N1A—C2A—S2A	178.6 (2)	C6B—N1B—C2B—S2B	−179.7 (2)
N1A—C2A—N3A—C4A	0.1 (4)	N1B—C2B—N3B—C4B	0.2 (4)
S2A—C2A—N3A—C4A	179.9 (2)	S2B—C2B—N3B—C4B	−179.2 (2)
C2A—N3A—C4A—O4A	−179.9 (3)	C2B—N3B—C4B—O4B	178.3 (3)
C2A—N3A—C4A—C5A	1.0 (4)	C2B—N3B—C4B—C5B	−2.7 (4)
O4A—C4A—C5A—C6A	−179.8 (3)	O4B—C4B—C5B—C6B	−176.7 (3)
N3A—C4A—C5A—C6A	−0.8 (4)	N3B—C4B—C5B—C6B	4.4 (4)
C4A—C5A—C6A—N1A	−0.5 (4)	C4B—C5B—C6B—N1B	−3.6 (4)
C4A—C5A—C6A—C7A	179.0 (3)	C4B—C5B—C6B—C7B	176.3 (3)
C2A—N1A—C6A—C5A	1.7 (4)	C2B—N1B—C6B—C5B	0.9 (4)
C2A—N1A—C6A—C7A	−177.8 (3)	C2B—N1B—C6B—C7B	−179.0 (3)
C5A—C6A—C7A—C8A	−26.6 (4)	C5B—C6B—C7B—C8B	−31.3 (5)
N1A—C6A—C7A—C8A	152.9 (3)	N1B—C6B—C7B—C8B	148.6 (3)
C6A—C7A—C8A—C9A	−174.9 (3)	C6B—C7B—C8B—C9B	−178.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···S2B^i	0.88	2.48	3.341 (2)	165
N3A—H3A···O4B	0.88	1.94	2.797 (3)	163
N1B—H1B···S2A^ii	0.88	2.50	3.361 (2)	167
N3B—H3B···O4A	0.88	1.98	2.826 (3)	161

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