2,4,6-Tris­(methyl­thio)-1,3,5-triazine, 3-methyl-4,6-bis­(methyl­thio)-1,3,5-triazine-2(3H)-thione, 1,3-di­methyl-4-methyl­thio-1,3,5-triazine-2,6(1H,3H)-di­thione and 1,3,5-tri­methyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trithione

The crystal structures of four isomers of C₆H₉N₃S₃ were determined. Their mol­ecules tend to be planar, but the tendency is weakened when the number of formal N=C double bonds in the ring decreases. The structures of the triazine rings in the four compounds were found to be similar to their oxy analogues. All of the compounds form planar layer structures with similar interlayer spacing ranging from 3.41 to 3.60 Å. The molecular packing of each isomer is controlled by weak van der Waals interactions.

S1. Comment

The crystal structures and thermal stability of trimethyl-substituted derivatives of mono-, di-, and tri-thiocyanuric acids have been studied in relation to the tendency of some of these compounds to undergo methyl rearrangements in the solid or liquid state (Paoloni et al., 1968; Tosato, 1982, 1984; Kaftory & Handelsman-Benory, 1994; Handelsman-Benory et al., 1995). The order of the methyl rearrangements in the oxygen analogues of the title compounds is (I_O)→(II_O)→(III_O)→(IV_O), and the reactions take place in the liquid or in the solid state. The corresponding sulfur compounds display an opposite tendency to methyl rearrangements: (IV)→(III)→(II)→(I) and none of the reactions takes place in the solid state (see Figures 1–4). \sch

There are three molecules of (III) and two in (IV) in the asymmetric unit. No statistically significant differences in the values of bond lengths and angles were found.

Molecules of (I) and (II) lie in crystallographic mirror planes and molecules of (I) have threefold symmetry. Their planarity can be explained by an effective conjugation of N═C double bonds resulting from six and five pure sp² hybridized atoms in the rings, respectively. On the other hand, r.m.s. deviations of the ring mean planes are 0.0075, 0.0142 and 0.0198 Å for the crystallographically independent molecules of (III) and 0.0391 and 0.0400 Å for (IV) (see Table 1). It should be noted that the molecules of trimethyl-substituted derivatives of cyanuric acid, the oxy analogues of compounds (I), (II) and (III) (Glowka & Iwanicka, 1989; Handelsman-Benory et al., 1995) are planar with r.m.s. deviations of the ring mean plane less than 0.01 Å. In molecules of the oxy analogue of (IV) the deviations are 0.0084 and 0.0145 Å for two crystallographically independent molecules (Thalladi et al., 1998). In general, the planarity of the triazine ring decreases with an increase in the number of sulfur atoms adjacent to methyl groups [such as in (III) and (IV)]. This tendency is a result of steric repulsion between the methyl group and the sulfur atom, which is more pronounced than that in the oxy analogues.

From their work on s-triazine derivatives, Glowka & Iwanicka (1989) concluded that the endocyclic bond angles at all N atoms are less than 120° while those at the C atoms are larger than 120°, irrespective of their hybridization. However, from the crystal structures of the title compounds it was found that whenever there is no formally endocyclic double bond at the particular atoms, the above conclusion does not hold. Bond angles at the sp³ hybridized N atoms range from 119.5 (2) to 126.1 (4)° and at the sp² C atom (as thiocarbonyl) from 113.6 (4) to 118.2 (2)°.

HF/6–31G* (d, p) ab initio calculation (Greenberg & Kaftory, 1999) with full optimization of the molecular geometry of (I) and its mono-, di- and tri-oxy analogues reveals that the alternation of the C—N bond lengths observed in the oxy compound (I_O) (Krygowski et al., 1997) hold also in the thio analogues. The C—N bonds that are cis to a methoxy or to a methylthio group are ca 0.015 Å shorter than the bonds that are trans to these groups. Krygowski et al. (1997) explain this phenomenon as a result of the `angular substituent effect' that enhances double-bond character of the adjacent C—N bond cis to these groups. This effect was found to be additive and supports the experimental results whereby all the methoxy (or methylthio) groups bend in the same sense (all clockwise or all anti-clockwise).

The effect of replacing the oxygen atoms by sulfur atoms on the geometries within the rings is minimal (see Table 1). However, the bond length alternation in (II) reveals that conjugation between the two C═N bonds is preferable to conjugation of C═N with C═S. Therefore the C6—N5 bond is shorter [1.342 (6) Å] than C2—N1 [1.359 (5) Å]. The ring structure of (III) shows that since the C6═S6 bond is strongly conjugated with C4═ N5, the lone pair at N1 prefers conjugation with C2═S2 to that with C6═ S6. As a result the C2—N1 bond [1.370 (4) Å] is shorter than C6—N1 [1.392 (5) Å].

In spite of the fact that the isomers crystallize in different crystallographic systems, all of them form planar layer structures with similar interlayer spacing in the range of 3.41 to 3.60 Å, approximately twice the Van der Waals radius of sulfur. For all four compounds the interlayer distances are 0.12–0.22 Å longer than those of the corresponding oxy analogues (see Table 1). The molecular volume in all four compounds lie in a relatively narrow range of 238–252 ų. The crystal packings all show no abnormally short intermolecular contacts, either within or between the layers. It can be concluded that the crystal arrangements of all the isomers are controlled by weak Van-der-Waals bonds.

S2. Experimental

The title compounds were synthesized by methylation of trithiocyanuric acid with diazomethane according to Tosato & Paoloni (1966). Crystals of (I) were obtained from a chloroform solution, crystals of (II) and (III) from ethyl acetate solutions and crystals of (IV) from ethanol by slow evaporation of the solvent at room temperature.

S3. Refinement

The coordinates of H atoms in molecules of (I) and in the methyl groups C2 and C4 of (II) were refined, the positions of all other hydrogen atoms in (II), (III) and (IV) were calculated. The calculated transmission factors for (II) are 0.807–0.966, but no absorption correction was applied. The data for (III) are 91.4% complete to 2 θ 55.0°. The absolute structure of (IV) was determined using 1644 Friedel pairs.

Computing details

Data collection: Philips PW 1100/20 (Philips, 1973) for (I), (II); COLLECT (Nonius, 1998) for (III); Kappa-CCD Software (Nonius, 1998) for (IV). Cell refinement: Philips PW 1100/20 for (I), (II); DENZO-SMN (Otwinowski & Minor, 1997) for (III); DENZO-SMN (Otwinowski & Minor,1997) for (IV). Data reduction: PROCN (Hornstra & Stubbe, 1973; Goldberg, 1990) for (I), (II); DENZO-SMN for (III), (IV). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEPII (Johnson, 1976) and TEXSAN (Molecular Structure Corporation, 1995 for (I); ORTEPII (Johnson, 1976) and TEXSAN (Molecular Structure Corporation, 1995) for (II), (III), (IV). Software used to prepare material for publication: WORD (Microsoft, 1998) for (I), (II), (III); WORD (Microsoft, 1995) for (IV).

Figures

	Fig. 1. ORTEPII (Johnson, 1976) drawing of (I) showing atomic numbering. Symmetry codes: (i) -x + y,-x,z; (ii) -y,x-y,z. Ellipsoids of atomic displacement for non-hydrogen atoms are drawn at the 50% probability level. H atoms are drawn as small circles of arbitrary radius.
	Fig. 2. ORTEPII (Johnson, 1976) drawing of (II) showing atomic numbering. Ellipsoids of atomic displacement for non-hydrogen atoms are drawn at the 50% probability level. H atoms are drawn as small circles of arbitrary radius.
	Fig. 3. ORTEPII (Johnson, 1976) drawing of one independent molecule (A) of (III) showing atomic numbering. Ellipsoids of atomic displacement for non-hydrogen atoms are drawn at the 50% probability level. H atoms are drawn as small circles of arbitrary radius.
	Fig. 4. ORTEPII (Johnson, 1976) drawing of one independent molecule (A) of (IV) showing atomic numbering. Ellipsoids of atomic displacement for non-hydrogen atoms are drawn at the 50% probability level. H atoms are drawn as small circles of arbitrary radius.

(I) 2,4,6-Tris(methylthio)-1,3,5-triazine

Crystal data

C6H9N3S3	Dx = 1.529 Mg m^−3
Mr = 219.34	Mo Kα radiation, λ = 0.71070 Å
Hexagonal, P63/m	Cell parameters from 25 reflections
a = 8.898 (2) Å	θ = 2.6–12.0°
c = 6.947 (2) Å	µ = 0.73 mm^−1
V = 476.3 (2) Å^3	T = 293 K
Z = 2	Hexagonal prism, colourless
F(000) = 228	0.20 × 0.14 × 0.12 mm

Data collection

PHILIPS PW 1100 four-circle diffractometer	Rint = 0.084
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.6°
Graphite monochromator	h = 0→10
ω/2θ scans	k = −10→9
1053 measured reflections	l = −8→0
313 independent reflections	3 standard reflections every 120 min min
226 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.034	Only H-atom coordinates refined
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0324P)^2 + 0.0347P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
313 reflections	Δρmax = 0.23 e Å^−3
31 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.033 (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
S1	0.38593 (13)	0.12173 (12)	0.2500	0.0448 (4)
N1	0.0500 (4)	−0.1246 (4)	0.2500	0.0367 (9)
C1	0.3932 (6)	−0.0766 (6)	0.2500	0.0504 (13)
C2	0.1621 (5)	0.0458 (5)	0.2500	0.0353 (11)
H1	0.331 (4)	−0.148 (4)	0.140 (4)	0.053*
H2	0.509 (7)	−0.044 (6)	0.2500	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0283 (6)	0.0336 (6)	0.0707 (8)	0.0142 (5)	0.000	0.000
N1	0.034 (2)	0.0327 (18)	0.0452 (19)	0.0175 (16)	0.000	0.000
C1	0.031 (2)	0.038 (2)	0.084 (4)	0.018 (2)	0.000	0.000
C2	0.032 (2)	0.036 (2)	0.037 (2)	0.0171 (19)	0.000	0.000

Geometric parameters (Å, º)

S1—C2	1.754 (4)	C1—H1	0.97 (3)
S1—C1	1.798 (5)	C1—H2	0.92 (5)
N1—C2	1.335 (5)	C2—N1^ii	1.344 (5)
N1—C2^i	1.344 (5)
C2—S1—C1	102.3 (2)	S1—C1—H1	110.9 (18)
C2—N1—C2^i	112.8 (5)	S1—C1—H2	106 (3)
N1—C2—S1	119.8 (3)	N1—C2—N1^ii	127.2 (5)
N1^ii—C2—S1	112.9 (3)	H1—C1—H2	112 (2)

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

(II) 3-Methyl-4,6-bismethylthio-1,3,5-triazine-2(3H)-thione

Crystal data

C6H9N3S3	Dx = 1.446 Mg m^−3
Mr = 219.34	Mo Kα radiation, λ = 0.71070 Å
Orthorhombic, Pnma	Cell parameters from 25 reflections
a = 16.566 (6) Å	θ = 2.5–18.2°
b = 6.813 (2) Å	µ = 0.69 mm^−1
c = 8.926 (3) Å	T = 293 K
V = 1007.4 (6) Å^3	Plate, light yellow
Z = 4	0.32 × 0.29 × 0.05 mm
F(000) = 456

Data collection

PHILIPS PW 1100 four-circle diffractometer	Rint = 0.060
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.5°
Graphite monochromator	h = −19→19
ω/2θ scans	k = −8→0
2410 measured reflections	l = −10→10
970 independent reflections	3 standard reflections every 120 min min
732 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0534P)^2 + 0.3375P] where P = (Fo^2 + 2Fc^2)/3
970 reflections	(Δ/σ)max < 0.001
83 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.22 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
S2	0.45212 (7)	0.2500	0.65758 (14)	0.0570 (4)
S4	0.51432 (8)	0.2500	0.07563 (14)	0.0616 (4)
S6	0.75133 (6)	0.2500	0.45694 (16)	0.0752 (6)
N1	0.59895 (18)	0.2500	0.5463 (4)	0.0423 (9)
N3	0.49389 (18)	0.2500	0.3690 (4)	0.0409 (9)
N5	0.6277 (2)	0.2500	0.2848 (4)	0.0469 (9)
C2	0.5184 (2)	0.2500	0.5175 (5)	0.0390 (10)
C3	0.4074 (3)	0.2500	0.3306 (7)	0.0636 (16)
H31	0.381 (3)	0.2500	0.413 (8)	0.095*
H32	0.401 (3)	0.140 (6)	0.290 (5)	0.095*
C4	0.5496 (3)	0.2500	0.2578 (5)	0.0424 (10)
C44	0.6063 (4)	0.2500	−0.0279 (7)	0.0796 (18)
H41	0.591 (4)	0.2500	−0.123 (9)	0.119*
H42	0.639 (3)	0.145 (7)	−0.005 (5)	0.119*
C6	0.6474 (2)	0.2500	0.4305 (5)	0.0436 (11)
C66	0.7610 (3)	0.2500	0.6567 (7)	0.095 (2)
H61	0.8172	0.2500	0.6833	0.143*
H62	0.7356	0.1349	0.6970	0.143*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S2	0.0518 (7)	0.0604 (9)	0.0587 (8)	0.000	0.0182 (6)	0.000
S4	0.0784 (9)	0.0646 (10)	0.0419 (7)	0.000	−0.0174 (6)	0.000
S6	0.0348 (6)	0.1256 (15)	0.0650 (9)	0.000	−0.0008 (6)	0.000
N1	0.0385 (17)	0.053 (2)	0.0350 (17)	0.000	−0.0011 (14)	0.000
N3	0.0378 (17)	0.041 (2)	0.044 (2)	0.000	−0.0084 (15)	0.000
N5	0.050 (2)	0.053 (2)	0.0375 (19)	0.000	0.0028 (15)	0.000
C2	0.041 (2)	0.031 (2)	0.045 (2)	0.000	0.0026 (18)	0.000
C3	0.043 (3)	0.078 (5)	0.070 (4)	0.000	−0.018 (2)	0.000
C4	0.054 (2)	0.036 (2)	0.036 (2)	0.000	−0.0065 (18)	0.000
C44	0.101 (5)	0.096 (5)	0.042 (3)	0.000	−0.001 (3)	0.000
C6	0.038 (2)	0.053 (3)	0.039 (2)	0.000	−0.0004 (16)	0.000
C66	0.055 (3)	0.159 (7)	0.072 (4)	0.000	−0.026 (3)	0.000

Geometric parameters (Å, º)

S2—C2	1.664 (4)	N3—C4	1.356 (6)
S4—C4	1.728 (4)	N3—C3	1.474 (5)
S4—C44	1.782 (7)	N5—C4	1.315 (5)
S6—C6	1.738 (4)	N5—C6	1.341 (5)
S6—C66	1.790 (6)	C3—H31	0.86 (6)
N1—C2	1.359 (5)	C3—H32	0.84 (4)
N1—C6	1.309 (5)	C44—H41	0.88 (8)
N3—C2	1.386 (5)	C44—H42	0.92 (4)
N1—C2—S2	120.4 (3)	C2—N3—C3	120.5 (4)
N1—C2—N3	118.0 (3)	C4—N3—C3	119.5 (4)
N1—C6—N5	128.1 (4)	C4—N5—C6	114.7 (3)
N1—C6—S6	120.0 (3)	C6—S6—C66	103.0 (2)
N3—C2—S2	121.7 (3)	C6—N1—C2	116.9 (3)
N3—C4—S4	117.3 (3)	S4—C44—H41	104 (5)
N5—C4—S4	120.3 (3)	S4—C44—H42	113 (3)
N5—C4—N3	122.4 (4)	N3—C3—H31	108 (4)
N5—C6—S6	111.9 (3)	N3—C3—H32	103 (3)
C4—S4—C44	101.5 (3)	H31—C3—H32	107 (3)
C4—N3—C2	120.0 (3)	H41—C44—H42	113 (4)

(III) 1,3-Dimethyl-4-methylthio-1,3,5-triazine-2,6(1H,3H)-dithione

Crystal data

C6H9N3S3	Z = 6
Mr = 219.34	F(000) = 684
Triclinic, P1	Dx = 1.533 Mg m^−3
a = 9.618 (5) Å	Mo Kα radiation, λ = 0.71070 Å
b = 11.435 (6) Å	Cell parameters from 5974 reflections
c = 13.910 (7) Å	θ = 2.2–27.5°
α = 107.30 (5)°	µ = 0.73 mm^−1
β = 100.65 (5)°	T = 293 K
γ = 93.05 (5)°	Trigonal prism, yellow
V = 1425.9 (2) Å^3	0.30 × 0.15 × 0.10 mm

Data collection

Kappa CCD diffractometer	4595 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 27.5°, θmin = 2.2°
Detector resolution: 56 microns pixels mm^-1	h = 0→12
ϕ scans	k = −14→14
21286 measured reflections	l = −16→16
5970 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0549P)^2 + 0.5239P] where P = (Fo^2 + 2Fc^2)/3
5970 reflections	(Δ/σ)max = 0.002
334 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.34 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
S2A	0.51892 (8)	0.49176 (6)	0.31593 (6)	0.0636 (2)
S4A	0.93909 (7)	0.25962 (6)	0.44949 (4)	0.04772 (16)
S6A	0.69820 (7)	0.11600 (6)	0.05616 (5)	0.05675 (19)
N1A	0.61718 (18)	0.30058 (16)	0.19507 (13)	0.0401 (4)
N3A	0.73020 (19)	0.36776 (16)	0.36865 (13)	0.0392 (4)
N5A	0.80135 (19)	0.19475 (16)	0.25529 (13)	0.0394 (4)
C1A	0.5083 (3)	0.3089 (2)	0.10773 (19)	0.0573 (7)
H11A	0.4664	0.3844	0.1284	0.086*
H12A	0.4356	0.2402	0.0873	0.086*
H13A	0.5521	0.3076	0.0508	0.086*
C2A	0.6250 (2)	0.38237 (19)	0.29060 (17)	0.0406 (5)
C3A	0.7568 (3)	0.4605 (2)	0.47237 (19)	0.0596 (7)
H31A	0.7954	0.4230	0.5232	0.089*
H32A	0.6689	0.4909	0.4859	0.089*
H33A	0.8234	0.5276	0.4752	0.089*
C4A	0.8129 (2)	0.27291 (19)	0.34617 (16)	0.0372 (4)
C44A	1.0106 (3)	0.1215 (2)	0.38828 (19)	0.0539 (6)
H41A	0.9345	0.0558	0.3555	0.081*
H42A	1.0764	0.0993	0.4390	0.081*
H43A	1.0591	0.1354	0.3376	0.081*
C6A	0.7063 (2)	0.20793 (19)	0.17443 (16)	0.0383 (5)
S2B	0.03958 (8)	0.46521 (6)	−0.28445 (5)	0.05496 (18)
S4B	−0.10679 (7)	0.84238 (5)	−0.00825 (5)	0.04970 (17)
S6B	0.27355 (7)	0.57615 (6)	0.11469 (5)	0.05465 (18)
N1B	0.1499 (2)	0.53268 (15)	−0.08289 (14)	0.0406 (4)
N3B	−0.02261 (19)	0.64953 (16)	−0.13564 (13)	0.0393 (4)
N5B	0.08003 (19)	0.69758 (15)	0.04075 (13)	0.0391 (4)
C1B	0.2371 (3)	0.4292 (2)	−0.1077 (2)	0.0653 (8)
H11B	0.1773	0.3564	−0.1526	0.098*
H12B	0.2814	0.4143	−0.0453	0.098*
H13B	0.3093	0.4498	−0.1412	0.098*
C2B	0.0569 (2)	0.55157 (18)	−0.16363 (16)	0.0385 (5)
C3B	−0.1269 (3)	0.6755 (3)	−0.2158 (2)	0.0606 (7)
H31B	−0.2145	0.6234	−0.2292	0.091*
H32B	−0.0906	0.6596	−0.2777	0.091*
H33B	−0.1438	0.7603	−0.1929	0.091*
C4B	−0.0052 (2)	0.71859 (18)	−0.03475 (17)	0.0379 (4)
C44B	−0.0367 (3)	0.9128 (2)	0.12699 (19)	0.0594 (7)
H41B	−0.0574	0.8567	0.1632	0.089*
H42B	−0.0796	0.9869	0.1513	0.089*
H43B	0.0646	0.9325	0.1388	0.089*
C6B	0.1626 (2)	0.60347 (18)	0.01950 (16)	0.0374 (4)
S2C	0.63244 (8)	0.92140 (7)	0.77534 (5)	0.06005 (19)
S4C	0.34295 (7)	0.78616 (5)	0.38887 (4)	0.04609 (16)
S6C	0.23512 (8)	1.18550 (6)	0.65611 (5)	0.05621 (19)
N1C	0.4244 (2)	1.03988 (16)	0.70662 (13)	0.0406 (4)
N3C	0.48270 (19)	0.87142 (16)	0.58428 (14)	0.0395 (4)
N5C	0.30184 (19)	0.98447 (15)	0.53279 (13)	0.0389 (4)
C1C	0.4474 (3)	1.1235 (3)	0.81431 (18)	0.0673 (8)
H11C	0.4662	1.0765	0.8611	0.101*
H12C	0.3637	1.1638	0.8241	0.101*
H13C	0.5271	1.1843	0.8272	0.101*
C2C	0.5093 (2)	0.94582 (19)	0.68588 (17)	0.0406 (5)
C3C	0.5713 (3)	0.7698 (2)	0.5533 (2)	0.0555 (6)
H31C	0.5206	0.7092	0.4909	0.083*
H32C	0.5916	0.7324	0.6069	0.083*
H33C	0.6589	0.8023	0.5421	0.083*
C4C	0.3764 (2)	0.89200 (18)	0.51229 (16)	0.0373 (4)
C44C	0.1885 (3)	0.8383 (2)	0.32802 (18)	0.0514 (6)
H41C	0.1127	0.8338	0.3636	0.077*
H42C	0.1592	0.7870	0.2576	0.077*
H43C	0.2107	0.9220	0.3303	0.077*
C6C	0.3251 (2)	1.06463 (18)	0.63037 (16)	0.0384 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S2A	0.0658 (4)	0.0561 (4)	0.0634 (4)	0.0318 (3)	0.0103 (3)	0.0081 (3)
S4A	0.0501 (3)	0.0530 (3)	0.0349 (3)	0.0069 (3)	−0.0016 (2)	0.0123 (2)
S6A	0.0623 (4)	0.0616 (4)	0.0353 (3)	0.0236 (3)	0.0006 (3)	0.0018 (3)
N1A	0.0364 (9)	0.0429 (10)	0.0369 (10)	0.0086 (8)	0.0009 (7)	0.0100 (7)
N3A	0.0425 (10)	0.0374 (9)	0.0324 (10)	0.0053 (7)	0.0047 (7)	0.0050 (7)
N5A	0.0390 (10)	0.0390 (9)	0.0366 (10)	0.0097 (7)	0.0028 (7)	0.0090 (7)
C1A	0.0518 (14)	0.0665 (16)	0.0458 (14)	0.0239 (12)	−0.0061 (11)	0.0128 (11)
C2A	0.0391 (11)	0.0370 (11)	0.0439 (13)	0.0051 (9)	0.0082 (9)	0.0102 (9)
C3A	0.0676 (17)	0.0548 (15)	0.0418 (14)	0.0070 (12)	0.0049 (12)	−0.0027 (11)
C4A	0.0348 (10)	0.0382 (11)	0.0375 (12)	0.0031 (8)	0.0050 (8)	0.0121 (8)
C44A	0.0501 (14)	0.0581 (15)	0.0512 (15)	0.0144 (11)	0.0025 (11)	0.0174 (11)
C6A	0.0355 (11)	0.0382 (11)	0.0375 (12)	0.0038 (8)	0.0036 (8)	0.0088 (8)
S2B	0.0691 (4)	0.0526 (4)	0.0344 (3)	0.0060 (3)	0.0094 (3)	0.0018 (2)
S4B	0.0497 (4)	0.0463 (3)	0.0491 (4)	0.0216 (3)	0.0034 (3)	0.0105 (2)
S6B	0.0673 (4)	0.0549 (4)	0.0409 (4)	0.0292 (3)	0.0032 (3)	0.0149 (3)
N1B	0.0507 (11)	0.0337 (9)	0.0367 (10)	0.0145 (8)	0.0103 (8)	0.0077 (7)
N3B	0.0389 (10)	0.0430 (10)	0.0340 (10)	0.0070 (8)	0.0031 (7)	0.0114 (7)
N5B	0.0447 (10)	0.0355 (9)	0.0359 (10)	0.0133 (8)	0.0071 (7)	0.0090 (7)
C1B	0.088 (2)	0.0505 (14)	0.0576 (17)	0.0391 (14)	0.0206 (14)	0.0088 (11)
C2B	0.0431 (12)	0.0343 (10)	0.0357 (12)	0.0003 (9)	0.0089 (9)	0.0079 (8)
C3B	0.0554 (15)	0.0797 (18)	0.0451 (15)	0.0216 (14)	−0.0005 (11)	0.0213 (12)
C4B	0.0370 (11)	0.0342 (10)	0.0416 (12)	0.0066 (8)	0.0074 (8)	0.0106 (8)
C44B	0.0639 (16)	0.0501 (14)	0.0535 (15)	0.0250 (12)	0.0029 (12)	0.0029 (11)
C6B	0.0429 (11)	0.0320 (10)	0.0370 (12)	0.0073 (8)	0.0094 (9)	0.0090 (8)
S2C	0.0605 (4)	0.0665 (4)	0.0520 (4)	0.0162 (3)	−0.0031 (3)	0.0242 (3)
S4C	0.0522 (3)	0.0415 (3)	0.0389 (3)	0.0129 (2)	0.0102 (2)	0.0023 (2)
S6C	0.0668 (4)	0.0477 (3)	0.0461 (4)	0.0261 (3)	0.0079 (3)	0.0017 (3)
N1C	0.0503 (11)	0.0363 (9)	0.0316 (10)	0.0081 (8)	0.0065 (7)	0.0061 (7)
N3C	0.0394 (10)	0.0384 (9)	0.0407 (10)	0.0112 (7)	0.0101 (7)	0.0102 (7)
N5C	0.0406 (10)	0.0361 (9)	0.0357 (10)	0.0083 (7)	0.0056 (7)	0.0056 (7)
C1C	0.086 (2)	0.0656 (17)	0.0358 (14)	0.0194 (15)	−0.0005 (13)	−0.0006 (11)
C2C	0.0397 (12)	0.0393 (11)	0.0437 (13)	0.0028 (9)	0.0068 (9)	0.0157 (9)
C3C	0.0539 (15)	0.0524 (14)	0.0614 (16)	0.0260 (12)	0.0154 (12)	0.0144 (11)
C4C	0.0401 (11)	0.0339 (10)	0.0370 (12)	0.0041 (8)	0.0094 (8)	0.0088 (8)
C44C	0.0573 (15)	0.0476 (13)	0.0412 (13)	0.0103 (11)	0.0013 (10)	0.0065 (10)
C6C	0.0397 (11)	0.0344 (10)	0.0388 (12)	0.0035 (8)	0.0078 (9)	0.0085 (8)

Geometric parameters (Å, º)

S2A—C2A	1.654 (2)	N1B—C6B	1.392 (3)
S4A—C4A	1.751 (2)	N3B—C2B	1.390 (3)
S4A—C44A	1.796 (3)	N3B—C3B	1.467 (3)
S6A—C6A	1.653 (2)	N3B—C4B	1.364 (3)
N1A—C1A	1.480 (3)	N5B—C4B	1.298 (3)
N1A—C2A	1.365 (3)	N5B—C6B	1.366 (3)
N1A—C6A	1.395 (3)	S2C—C2C	1.651 (2)
N3A—C2A	1.397 (3)	S4C—C4C	1.742 (2)
N3A—C3A	1.482 (3)	S4C—C44C	1.791 (3)
N3A—C4A	1.374 (3)	S6C—C6C	1.654 (2)
N5A—C4A	1.294 (3)	N1C—C1C	1.487 (3)
N5A—C6A	1.363 (3)	N1C—C2C	1.380 (3)
S2B—C2B	1.649 (2)	N1C—C6C	1.396 (3)
S4B—C4B	1.751 (2)	N3C—C2C	1.384 (3)
S4B—C44B	1.793 (3)	N3C—C3C	1.485 (3)
S6B—C6B	1.658 (2)	N3C—C4C	1.375 (3)
N1B—C1B	1.481 (3)	N5C—C4C	1.300 (3)
N1B—C2B	1.379 (3)	N5C—C6C	1.363 (3)
N1A—C2A—S2A	123.95 (17)	C2B—N1B—C1B	117.43 (19)
N1A—C2A—N3A	115.25 (19)	C2B—N1B—C6B	123.40 (18)
N1A—C6A—S6A	121.68 (16)	C2B—N3B—C3B	118.99 (19)
N3A—C2A—S2A	120.80 (17)	C4B—S4B—C44B	100.62 (12)
N3A—C4A—S4A	116.28 (16)	C4B—N3B—C2B	120.14 (18)
N5A—C4A—S4A	119.64 (17)	C4B—N3B—C3B	120.86 (19)
N5A—C4A—N3A	124.07 (19)	C4B—N5B—C6B	119.08 (19)
N5A—C6A—S6A	120.40 (17)	C6B—N1B—C1B	119.15 (19)
N5A—C6A—N1A	117.92 (19)	C2C—N1C—C1C	117.96 (19)
C2A—N1A—C1A	118.94 (19)	C2C—N1C—C6C	123.06 (19)
C2A—N1A—C6A	123.63 (18)	C2C—N3C—C3C	119.34 (19)
C2A—N3A—C3A	118.94 (19)	C4C—S4C—C44C	101.14 (12)
C4A—S4A—C44A	101.07 (12)	C4C—N3C—C2C	120.47 (18)
C4A—N3A—C2A	119.52 (18)	C4C—N3C—C3C	120.18 (19)
C4A—N3A—C3A	121.39 (19)	C4C—N5C—C6C	119.81 (19)
C4A—N5A—C6A	119.43 (19)	C6C—N1C—C1C	118.84 (19)
C6A—N1A—C1A	117.43 (19)	N1C—C2C—N3C	115.13 (19)
N1B—C2B—S2B	123.14 (17)	N1C—C2C—S2C	122.92 (18)
N1B—C2B—N3B	114.85 (19)	N1C—C6C—S6C	121.90 (16)
N1B—C6B—S6B	121.97 (16)	N3C—C2C—S2C	121.94 (17)
N3B—C2B—S2B	122.01 (17)	N3C—C4C—S4C	116.74 (16)
N3B—C4B—S4B	116.47 (16)	N5C—C4C—S4C	120.05 (17)
N5B—C4B—S4B	119.23 (17)	N5C—C4C—N3C	123.2 (2)
N5B—C4B—N3B	124.30 (19)	N5C—C6C—S6C	120.12 (17)
N5B—C6B—S6B	119.85 (17)	N5C—C6C—N1C	117.98 (19)
N5B—C6B—N1B	118.18 (19)
C1A—N1A—C2A—S2A	0.2 (3)	C3B—N3B—C4B—N5B	176.7 (2)
C1A—N1A—C2A—N3A	179.7 (2)	C4B—N3B—C2B—S2B	179.91 (16)
C1A—N1A—C6A—S6A	3.7 (3)	C4B—N3B—C2B—N1B	0.1 (3)
C1A—N1A—C6A—N5A	−176.2 (2)	C4B—N5B—C6B—S6B	179.28 (17)
C2A—N1A—C6A—S6A	−176.62 (17)	C4B—N5B—C6B—N1B	−1.0 (3)
C2A—N1A—C6A—N5A	3.5 (3)	C44B—S4B—C4B—N3B	−174.34 (18)
C2A—N3A—C4A—S4A	−178.51 (15)	C44B—S4B—C4B—N5B	6.0 (2)
C2A—N3A—C4A—N5A	0.8 (3)	C6B—N1B—C2B—S2B	−178.46 (16)
C3A—N3A—C2A—S2A	−7.0 (3)	C6B—N1B—C2B—N3B	1.4 (3)
C3A—N3A—C2A—N1A	173.5 (2)	C6B—N5B—C4B—N3B	2.5 (3)
C3A—N3A—C4A—S4A	5.9 (3)	C6B—N5B—C4B—S4B	−177.85 (16)
C3A—N3A—C4A—N5A	−174.8 (2)	C1C—N1C—C2C—S2C	1.0 (3)
C4A—N3A—C2A—S2A	177.34 (16)	C1C—N1C—C2C—N3C	−179.9 (2)
C4A—N3A—C2A—N1A	−2.2 (3)	C1C—N1C—C6C—S6C	1.2 (3)
C4A—N5A—C6A—S6A	175.24 (16)	C1C—N1C—C6C—N5C	−177.7 (2)
C4A—N5A—C6A—N1A	−4.9 (3)	C2C—N3C—C4C—S4C	−175.32 (15)
C44A—S4A—C4A—N3A	176.03 (17)	C2C—N3C—C4C—N5C	4.2 (3)
C44A—S4A—C4A—N5A	−3.4 (2)	C2C—N1C—C6C—S6C	−174.46 (17)
C6A—N1A—C2A—S2A	−179.48 (17)	C2C—N1C—C6C—N5C	6.6 (3)
C6A—N1A—C2A—N3A	0.1 (3)	C3C—N3C—C4C—S4C	5.4 (3)
C6A—N5A—C4A—S4A	−177.80 (16)	C3C—N3C—C2C—S2C	−2.7 (3)
C6A—N5A—C4A—N3A	2.9 (3)	C3C—N3C—C2C—N1C	178.16 (19)
C1B—N1B—C2B—S2B	−0.2 (3)	C3C—N3C—C4C—N5C	−175.0 (2)
C1B—N1B—C2B—N3B	179.7 (2)	C4C—N3C—C2C—S2C	178.00 (16)
C1B—N1B—C6B—S6B	0.5 (3)	C4C—N3C—C2C—N1C	−1.1 (3)
C1B—N1B—C6B—N5B	−179.3 (2)	C4C—N5C—C6C—S6C	177.64 (17)
C2B—N3B—C4B—S4B	178.26 (15)	C4C—N5C—C6C—N1C	−3.4 (3)
C2B—N3B—C4B—N5B	−2.1 (3)	C44C—S4C—C4C—N3C	173.79 (17)
C2B—N1B—C6B—S6B	178.78 (16)	C44C—S4C—C4C—N5C	−5.8 (2)
C2B—N1B—C6B—N5B	−1.0 (3)	C6C—N1C—C2C—S2C	176.67 (16)
C3B—N3B—C2B—S2B	1.1 (3)	C6C—N1C—C2C—N3C	−4.2 (3)
C3B—N3B—C2B—N1B	−178.7 (2)	C6C—N5C—C4C—S4C	177.74 (15)
C3B—N3B—C4B—S4B	−3.0 (3)	C6C—N5C—C4C—N3C	−1.8 (3)

(IV) 1,3,5-Trimethyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trithione

Crystal data

C6H9N3S3	F(000) = 912
Mr = 219.34	Dx = 1.504 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71070 Å
a = 15.247 (1) Å	Cell parameters from 3563 reflections
b = 8.792 (1) Å	θ = 1.4–25.4°
c = 16.165 (1) Å	µ = 0.71 mm^−1
β = 116.60 (1)°	T = 293 K
V = 1937.5 (1) Å^3	Trigonal prism, yellow
Z = 8	0.25 × 0.25 × 0.15 mm

Data collection

Nonius Kappa-CCD diffractometer	3323 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.083
Graphite monochromator	θmax = 25.4°, θmin = 1.4°
ϕ scans	h = 0→18
15863 measured reflections	k = −10→10
3563 independent reflections	l = −19→17

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.056	w = 1/[σ^2(Fo^2) + (0.0599P)^2 + 4.3506P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.149	(Δ/σ)max = 0.008
S = 1.14	Δρmax = 0.38 e Å^−3
3563 reflections	Δρmin = −0.32 e Å^−3
224 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0089 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.06 (14)

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
S2A	0.78211 (12)	0.58878 (16)	0.36399 (14)	0.0674 (4)
S4A	0.71877 (12)	1.17825 (16)	0.36675 (13)	0.0685 (5)
S6A	1.05704 (10)	0.9810 (2)	0.39094 (12)	0.0671 (5)
N1A	0.9123 (3)	0.7999 (5)	0.3771 (3)	0.0497 (10)
N3A	0.7694 (3)	0.8881 (4)	0.3785 (3)	0.0431 (9)
N5A	0.8803 (3)	1.0613 (5)	0.3694 (3)	0.0529 (11)
C1A	0.9748 (5)	0.6704 (8)	0.3757 (6)	0.0789 (19)
H11A	0.9340	0.5844	0.3461	0.118*
H12A	1.0201	0.6440	0.4380	0.118*
H13A	1.0105	0.6995	0.3421	0.118*
C2A	0.8225 (3)	0.7627 (6)	0.3729 (3)	0.0452 (11)
C3A	0.6804 (5)	0.8559 (9)	0.3921 (6)	0.082 (2)
H31A	0.6910	0.7654	0.4286	0.123*
H32A	0.6248	0.8417	0.3330	0.123*
H33A	0.6683	0.9400	0.4235	0.123*
C4A	0.7902 (3)	1.0382 (6)	0.3709 (3)	0.0428 (11)
C5A	0.9071 (6)	1.2172 (7)	0.3588 (6)	0.082 (2)
H51A	0.8497	1.2713	0.3167	0.124*
H52A	0.9545	1.2156	0.3349	0.124*
H53A	0.9348	1.2671	0.4179	0.124*
C6A	0.9466 (4)	0.9430 (6)	0.3792 (3)	0.0446 (11)
S2B	0.44426 (11)	0.7099 (2)	0.11826 (14)	0.0716 (5)
S4B	0.70323 (13)	0.31913 (16)	0.11122 (14)	0.0722 (5)
S6B	0.78327 (12)	0.90675 (16)	0.14314 (11)	0.0659 (4)
N1B	0.6159 (3)	0.7919 (4)	0.1277 (3)	0.0435 (9)
N3B	0.5873 (3)	0.5297 (4)	0.1279 (3)	0.0435 (9)
N5B	0.7287 (3)	0.6173 (5)	0.1171 (3)	0.0476 (9)
C1B	0.5855 (5)	0.9502 (6)	0.1282 (5)	0.0688 (16)
H11B	0.6296	0.9981	0.1851	0.103*
H12B	0.5202	0.9522	0.1227	0.103*
H13B	0.5869	1.0040	0.0771	0.103*
C2B	0.5516 (4)	0.6774 (6)	0.1250 (3)	0.0492 (11)
C3B	0.5322 (5)	0.4040 (7)	0.1391 (5)	0.0729 (17)
H31B	0.4978	0.4375	0.1731	0.109*
H32B	0.5764	0.3233	0.1723	0.109*
H33B	0.4859	0.3678	0.0794	0.109*
C4B	0.6730 (4)	0.4951 (6)	0.1187 (3)	0.0455 (11)
C5B	0.8167 (5)	0.5908 (8)	0.1040 (5)	0.0750 (18)
H51B	0.8394	0.6857	0.0914	0.113*
H52B	0.8011	0.5226	0.0530	0.113*
H53B	0.8670	0.5468	0.1592	0.113*
C6B	0.7067 (4)	0.7669 (5)	0.1285 (3)	0.0437 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S2A	0.0661 (9)	0.0429 (8)	0.0976 (11)	−0.0068 (7)	0.0404 (8)	−0.0010 (7)
S4A	0.0638 (9)	0.0467 (9)	0.1034 (12)	0.0146 (6)	0.0449 (9)	−0.0005 (7)
S6A	0.0444 (7)	0.0769 (11)	0.0856 (10)	−0.0073 (7)	0.0339 (7)	−0.0038 (8)
N1A	0.047 (2)	0.042 (2)	0.061 (2)	0.0025 (18)	0.0248 (19)	−0.0037 (19)
N3A	0.040 (2)	0.035 (2)	0.057 (2)	−0.0058 (16)	0.0247 (18)	0.0024 (17)
N5A	0.057 (3)	0.044 (2)	0.056 (2)	−0.0019 (19)	0.024 (2)	−0.0008 (19)
C1A	0.065 (4)	0.054 (4)	0.128 (6)	0.000 (3)	0.052 (4)	−0.011 (4)
C2A	0.034 (2)	0.051 (3)	0.048 (2)	0.002 (2)	0.0158 (19)	−0.002 (2)
C3A	0.058 (3)	0.090 (5)	0.119 (6)	0.001 (3)	0.059 (4)	0.014 (4)
C4A	0.038 (2)	0.044 (3)	0.049 (3)	0.0006 (19)	0.022 (2)	0.001 (2)
C5A	0.085 (5)	0.046 (3)	0.114 (6)	−0.001 (3)	0.043 (4)	0.015 (3)
C6A	0.047 (3)	0.048 (3)	0.044 (2)	0.005 (2)	0.025 (2)	−0.001 (2)
S2B	0.0478 (8)	0.0697 (11)	0.1036 (12)	0.0049 (7)	0.0396 (8)	−0.0025 (9)
S4B	0.0802 (11)	0.0409 (9)	0.1069 (13)	0.0099 (7)	0.0520 (10)	−0.0020 (8)
S6B	0.0697 (10)	0.0522 (9)	0.0809 (10)	−0.0190 (7)	0.0382 (8)	−0.0061 (7)
N1B	0.040 (2)	0.036 (2)	0.056 (2)	0.0020 (16)	0.0238 (17)	0.0016 (17)
N3B	0.039 (2)	0.039 (2)	0.059 (2)	0.0023 (17)	0.0283 (18)	−0.0031 (17)
N5B	0.049 (2)	0.048 (2)	0.051 (2)	−0.0045 (19)	0.0267 (18)	−0.0006 (18)
C1B	0.069 (4)	0.038 (3)	0.101 (5)	0.006 (3)	0.038 (3)	−0.004 (3)
C2B	0.051 (3)	0.045 (3)	0.048 (2)	0.006 (2)	0.020 (2)	−0.004 (2)
C3B	0.085 (4)	0.041 (3)	0.108 (5)	−0.012 (3)	0.056 (4)	0.007 (3)
C4B	0.050 (3)	0.042 (3)	0.045 (2)	−0.003 (2)	0.021 (2)	0.002 (2)
C5B	0.084 (4)	0.063 (4)	0.106 (5)	−0.003 (3)	0.068 (4)	−0.002 (4)
C6B	0.049 (3)	0.036 (2)	0.046 (3)	−0.006 (2)	0.021 (2)	−0.0013 (19)

Geometric parameters (Å, º)

S2A—C2A	1.631 (5)	S2B—C2B	1.616 (6)
S4A—C4A	1.626 (5)	S4B—C4B	1.634 (5)
S6A—C6A	1.642 (5)	S6B—C6B	1.638 (5)
N1A—C1A	1.491 (7)	N1B—C1B	1.469 (7)
N1A—C2A	1.379 (6)	N1B—C2B	1.392 (7)
N1A—C6A	1.356 (7)	N1B—C6B	1.396 (6)
N3A—C2A	1.395 (6)	N3B—C2B	1.400 (6)
N3A—C3A	1.496 (6)	N3B—C3B	1.448 (6)
N3A—C4A	1.376 (6)	N3B—C4B	1.413 (6)
N5A—C4A	1.399 (6)	N5B—C4B	1.377 (6)
N5A—C5A	1.463 (8)	N5B—C5B	1.467 (7)
N5A—C6A	1.409 (7)	N5B—C6B	1.390 (7)
N1A—C2A—S2A	123.7 (4)	N1B—C2B—S2B	123.5 (4)
N1A—C2A—N3A	113.6 (4)	N1B—C2B—N3B	114.3 (4)
N1A—C6A—S6A	123.7 (4)	N1B—C6B—S6B	121.5 (4)
N1A—C6A—N5A	115.6 (4)	N3B—C2B—S2B	122.2 (4)
N3A—C2A—S2A	122.6 (3)	N3B—C4B—S4B	121.1 (4)
N3A—C4A—S4A	123.6 (4)	N5B—C4B—S4B	122.7 (4)
N3A—C4A—N5A	114.1 (4)	N5B—C4B—N3B	116.2 (4)
N5A—C4A—S4A	122.3 (4)	N5B—C6B—S6B	122.1 (4)
N5A—C6A—S6A	120.6 (4)	N5B—C6B—N1B	116.4 (4)
C2A—N1A—C1A	116.4 (4)	C2B—N1B—C1B	117.8 (4)
C2A—N3A—C3A	116.8 (5)	C2B—N1B—C6B	124.6 (4)
C4A—N3A—C2A	126.1 (4)	C2B—N3B—C3B	118.3 (4)
C4A—N3A—C3A	117.1 (5)	C2B—N3B—C4B	124.1 (4)
C4A—N5A—C5A	117.8 (5)	C4B—N3B—C3B	117.7 (4)
C4A—N5A—C6A	123.5 (4)	C4B—N5B—C5B	119.3 (5)
C6A—N1A—C1A	117.8 (4)	C4B—N5B—C6B	123.3 (4)
C6A—N1A—C2A	125.7 (4)	C6B—N1B—C1B	117.6 (4)
C6A—N5A—C5A	118.7 (5)	C6B—N5B—C5B	117.4 (4)
C1A—N1A—C2A—S2A	−1.6 (7)	C1B—N1B—C2B—S2B	2.6 (7)
C6A—N1A—C2A—S2A	176.0 (4)	C6B—N1B—C2B—S2B	−176.4 (4)
C3A—N3A—C2A—S2A	10.0 (7)	C3B—N3B—C2B—S2B	−9.4 (7)
C4A—N3A—C2A—S2A	−168.6 (4)	C4B—N3B—C2B—S2B	169.3 (4)
C2A—N3A—C4A—S4A	173.0 (4)	C2B—N3B—C4B—S4B	−173.1 (4)
C3A—N3A—C4A—S4A	−5.6 (7)	C3B—N3B—C4B—S4B	5.6 (7)
C5A—N5A—C4A—S4A	−3.3 (7)	C5B—N5B—C4B—S4B	2.8 (7)
C6A—N5A—C4A—S4A	175.5 (4)	C6B—N5B—C4B—S4B	−176.3 (4)
C1A—N1A—C6A—S6A	−6.5 (7)	C1B—N1B—C6B—S6B	7.8 (7)
C2A—N1A—C6A—S6A	176.0 (4)	C2B—N1B—C6B—S6B	−173.2 (4)
C4A—N5A—C6A—S6A	−171.6 (4)	C4B—N5B—C6B—S6B	169.9 (4)
C5A—N5A—C6A—S6A	7.2 (7)	C5B—N5B—C6B—S6B	−9.3 (7)
C3A—N3A—C2A—N1A	−169.0 (5)	C3B—N3B—C2B—N1B	171.1 (5)
C4A—N3A—C2A—N1A	12.5 (7)	C4B—N3B—C2B—N1B	−10.2 (7)
C4A—N5A—C6A—N1A	9.0 (7)	C4B—N5B—C6B—N1B	−9.6 (7)
C5A—N5A—C6A—N1A	−172.1 (5)	C5B—N5B—C6B—N1B	171.2 (5)
C1A—N1A—C2A—N3A	177.4 (5)	C1B—N1B—C2B—N3B	−177.9 (5)
C6A—N1A—C2A—N3A	−5.1 (7)	C6B—N1B—C2B—N3B	3.1 (7)
C2A—N3A—C4A—N5A	−8.7 (7)	C5B—N5B—C4B—N3B	−177.6 (5)
C3A—N3A—C4A—N5A	172.7 (5)	C6B—N5B—C4B—N3B	3.3 (7)
C5A—N5A—C4A—N3A	178.3 (5)	C2B—N3B—C4B—N5B	7.4 (7)
C6A—N5A—C4A—N3A	−2.8 (7)	C3B—N3B—C4B—N5B	−174.0 (5)
C1A—N1A—C6A—N5A	172.8 (5)	C1B—N1B—C6B—N5B	−172.7 (5)
C2A—N1A—C6A—N5A	−4.7 (7)	C2B—N1B—C6B—N5B	6.3 (7)