3-(2-Furyl)-6-(4-methyl­phenyl)-7H-1,2,4-triazolo­[3,4-b][1,3,4]thia­diazine and its 6-phenyl analogue

In the title compounds, C₁₅H₁₂N₄OS, (I), and C₁₄H₁₀N₄OS, (II), the thia­diazine ring adopts a skew-boat conformation, while the triazole and furyl rings are essentially planar. The phenyl group is twisted by 33.5 (2) and 47.9 (1)° out of the triazole-ring plane in (I) and (II), respectively.

S1. Comment

The prevalence of resistant infections decreases the applicability of existing chemotherapeutic and chemopreventive antimicrobial agents and stimulates the search for new compounds. The 1,2,4-triazole nucleus and the nitrogen-bridged heterocycles derived from it have recently been incorporated into a variety of compounds with antibacterial (Holla & Kalluraya, 1988), antifungal (Prasad et al., 1989) and antiparasitic (El-Dawy et al., 1983) properties. In a previous work, we reported on the synthesis and the antimicrobial effects of novel 6-aryl-3-(2-furyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines (Ergenç et al., 1996). To further investigate this bicyclic system and establish its structure unambiguously, single-crystal X-ray diffraction studies were carried out on 6-phenyl- and 6-(4-methylphenyl)-3-(2-furyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine, i.e. (II) and (I), respectively.

The title compounds consist of a fused triazolo-thiadiazine system, one furyl ring and one phenyl ring. The four rings do not share a common plane. As expected, the 1,2,4-triazole and furanyl rings in both compounds are planar which can be attributed to a wide range of electron delocalization [maximum deviations 0.007 (2) and −0.003 (3) Å for C4 and C8, respectively, in (I), and −0.006 (2) and 0.003 (3) Å for N3 and C7 in (II)]. The thiadiazine ring fused to the triazole ring deviates from planarity. In (I) and (II), the puckering parameters (Cremer & Pople, 1975) are Q = 0.587 (2) and 0.616 (2) Å, θ = 65.8 (2) and 66.7 (2)°, and ϕ = 34.2 (2) and 34.6 (2)° for (I) and (II), respectively. So the thiadiazine moiety assumes a skew-boat conformation in both compounds. The phenyl ring is essentially planar and twisted out of the plane of the triazole ring, the dihedral angle between these planes is 33.5 (2)° in (I) and 47.9 (1)° in (II). The dihedral angles between the triazole and furyl rings are 16.2 (2) and 10.8 (1)° in (I) and (II), respectively.

The bond lengths and angles in both compounds are very similar and within expected ranges. The N1—C4 and N2—C3 bond distances [average values 1.311 (3) and 1.304 (3) Å, respectively] are in a good agreement with those found for structures containing the 1,2,4-triazole ring (Özbey et al., 1999; Wang et al., 1998). In both compounds, the presence of the electron-donating furyl group in the 3-position of the triazole ring leads to an elongation of the N1—N2 bond length to 1.402 (3) Å (average value). This bond is 1.371 (2) Å in 5-amino-3-trifluoromethyl-1H-1,2,4-triazole (Borbulevych et al., 1998), in which an electron-withdrawing group is bound to the 3-position of the triazole ring. The difference between the S1—C2 bond distance [average value 1.814 (3) Å] and the S1—C3 bond distance [average value 1.733 Å] can be attributed to the different hybridization of the Csp³ and Csp² atoms (Argay et al., 1977, 1980).

Since (I) is the 4-methyl derivative of (II), the identical space groups and the similarity of the lattice parameters suggest some degree of isostructurality, as shown by the descriptors Δ(pc) = 3.6% and Π = 0.034 (Kálmán et al., 1991, 1993). In terms of the predictions given by Kitaigorodskii (1961), it is unique that a relatively small molecule such as (I) (M_r = 296.35) retains similar close packing to that of (II) enlarged by the bulky methyl group (5% of the molecular weight). This, of course, accounts for the low index of isostructurality I_i(20) = 52% calculated by the algorithm of Kálmán et al. (1991, 1993). To avoid the ambivalence raised by the choice of a common origin for oblique (monoclinic) unit cells, the isostructuralities of (I) and (II) were calculated by the novel volumetric method developed by Fábián (1999) and reported in detail by Fábián & Kálmán (1999). The volumetric index of isostructurality amounts to 72% for the whole unit cell with four molecules indicating significant packing similarity of the related structures.

In both compounds, the N4 atom of the thiadiazine moiety is involved in an intramolecular hydrogen-bond interaction (Tables 2 and 4). In compound (I), there is also one intermolecular interaction (Table 2). These bonds, together with normal van der Waals interactions, are responsible for the packing in the crystal.

S2. Experimental

Both compounds were synthesized as described in Ergen˛c et al. (1996) and recrystallized from C₂H₅OH.

Computing details

For both compounds, data collection: CAD-4 EXPRESS (Enraf-Nonius, 1993); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: MolEN; program(s) used to refine structure: MolEN; molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: MolEN and PLATON (Spek, 1990).

Figures

	Fig. 1. ORTEPII (Johnson, 1976) drawing of (I). Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small circles of arbitrary radii.
	Fig. 2. ORTEPII (Johnson, 1976) drawing of (II). Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small circles of arbitrary radii.

(I)

Crystal data

C15H12N4OS	Z = 4
Mr = 296.35	Dx = 1.43 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.342 (1) Å	θ = 10.0–18.2°
b = 9.106 (1) Å	µ = 0.24 mm^−1
c = 16.208 (1) Å	T = 295 K
β = 92.58 (1)°	Prismatic, yellow
V = 1377.4 (2) Å^3	0.64 × 0.40 × 0.16 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.011
ω/2θ scans	θmax = 26.3°
Absorption correction: empirical (using intensity measurements) via ψ scans (Fair, 1990)	h = −11→0
Tmin = 0.940, Tmax = 1.000	k = −11→0
3072 measured reflections	l = −20→20
2705 independent reflections	3 standard reflections every 120 min
1890 reflections with I > 2σ(I)	intensity decay: 0.8%

Refinement

Refinement on F	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.038	w = 1/[σ(F^2) + (0.02F)^2 + 1]
wR(F^2) = 0.043	(Δ/σ)max < 0.001
S = 0.70	Δρmax = 0.25 e Å^−3
1890 reflections	Δρmin = −0.22 e Å^−3
190 parameters

Special details

Refinement. In (I) and (II), H atoms were placed geometrically 0.95 Å from their parent atoms except for the H atoms of C2, which were found from Δρ maps and refined isotropically for a few cycles and then fixed.

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

	x	y	z	Uiso*/Ueq
S1	0.55632 (7)	0.1903 (1)	0.78080 (4)	0.0557 (2)
O1	0.1516 (2)	0.4867 (2)	1.0204 (1)	0.0609 (5)
N1	0.2597 (2)	0.4417 (3)	0.8634 (1)	0.0508 (6)
N2	0.3277 (2)	0.3763 (3)	0.7975 (1)	0.0548 (6)
N3	0.4343 (2)	0.3028 (2)	0.9138 (1)	0.0380 (5)
N4	0.5366 (2)	0.2488 (2)	0.9707 (1)	0.0373 (5)
C1	0.6096 (2)	0.1374 (3)	0.9466 (1)	0.0363 (6)
C2	0.5779 (3)	0.0610 (3)	0.8655 (1)	0.0465 (6)
C3	0.4310 (3)	0.2958 (3)	0.8295 (1)	0.0447 (8)
C4	0.3256 (2)	0.3970 (3)	0.9320 (1)	0.0398 (6)
C5	0.2850 (2)	0.4286 (3)	1.0148 (1)	0.0407 (6)
C6	0.3450 (3)	0.4069 (3)	1.0908 (2)	0.0478 (8)
C7	0.2437 (3)	0.4545 (3)	1.1475 (2)	0.0590 (8)
C8	0.1298 (3)	0.5005 (4)	1.1027 (2)	0.0692 (8)
C9	0.7210 (2)	0.0814 (3)	1.0059 (1)	0.0356 (6)
C10	0.7611 (3)	0.1613 (3)	1.0766 (2)	0.0479 (6)
C11	0.8586 (3)	0.1051 (3)	1.1344 (2)	0.0530 (8)
C12	0.9217 (2)	−0.0314 (3)	1.1247 (1)	0.0450 (8)
C13	0.8846 (3)	−0.1081 (3)	1.0539 (2)	0.0467 (6)
C14	0.7862 (2)	−0.0541 (3)	0.9952 (1)	0.0424 (6)
C15	1.0259 (3)	−0.0929 (4)	1.1893 (2)	0.0667 (12)
H6	0.438	0.367	1.103	0.0621*
H7	0.256	0.454	1.206	0.0747*
H8	0.045	0.538	1.125	0.0874*
H10	0.720	0.255	1.085	0.0633*
H11	0.884	0.161	1.182	0.0684*
H13	0.928	−0.201	1.045	0.0608*
H14	0.763	−0.110	0.947	0.0557*
H21	0.486	0.004	0.867	0.0545*
H22	0.652	−0.006	0.849	0.0545*
H151	1.057	−0.187	1.172	0.0823*
H152	1.106	−0.029	1.196	0.0823*
H153	0.980	−0.102	1.240	0.0823*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0555 (3)	0.0822 (5)	0.0296 (3)	0.0068 (4)	0.0041 (2)	0.0008 (3)
O1	0.0518 (9)	0.080 (1)	0.0506 (9)	0.024 (1)	0.0001 (8)	0.001 (1)
N1	0.053 (1)	0.056 (1)	0.043 (1)	0.006 (1)	−0.0031 (9)	0.010 (1)
N2	0.057 (1)	0.070 (1)	0.037 (1)	0.007 (1)	−0.0038 (9)	0.012 (1)
N3	0.0364 (9)	0.047 (1)	0.0302 (8)	−0.0001 (9)	−0.0023 (7)	0.0031 (9)
N4	0.0366 (9)	0.044 (1)	0.0310 (8)	−0.0003 (9)	−0.0028 (7)	0.0025 (8)
C1	0.036 (1)	0.041 (1)	0.032 (1)	−0.005 (1)	0.0020 (9)	0.000 (1)
C2	0.049 (1)	0.053 (1)	0.037 (1)	0.000 (1)	−0.003 (1)	−0.008 (1)
C3	0.046 (1)	0.058 (2)	0.030 (1)	−0.004 (1)	−0.0004 (9)	0.007 (1)
C4	0.039 (1)	0.040 (1)	0.040 (1)	−0.001 (1)	−0.001 (1)	0.006 (1)
C5	0.038 (1)	0.038 (1)	0.046 (1)	0.003 (1)	−0.000 (1)	0.001 (1)
C6	0.043 (1)	0.055 (2)	0.045 (1)	0.006 (1)	−0.004 (1)	−0.003 (1)
C7	0.060 (1)	0.076 (2)	0.041 (1)	0.012 (2)	0.002 (1)	−0.011 (1)
C8	0.061 (1)	0.094 (2)	0.053 (1)	0.028 (2)	0.008 (1)	−0.008 (2)
C9	0.034 (1)	0.040 (1)	0.033 (1)	−0.003 (1)	0.0021 (9)	0.001 (1)
C10	0.050 (1)	0.050 (1)	0.043 (1)	0.008 (1)	−0.006 (1)	−0.008 (1)
C11	0.055 (1)	0.064 (2)	0.039 (1)	0.002 (1)	−0.010 (1)	−0.009 (1)
C12	0.037 (1)	0.056 (2)	0.042 (1)	−0.000 (1)	0.001 (1)	0.008 (1)
C13	0.043 (1)	0.039 (1)	0.058 (1)	0.002 (1)	0.001 (1)	0.004 (1)
C14	0.044 (1)	0.041 (1)	0.042 (1)	−0.005 (1)	−0.001 (1)	−0.005 (1)
C15	0.057 (2)	0.085 (2)	0.057 (2)	0.016 (2)	−0.008 (1)	0.011 (2)

Geometric parameters (Å, º)

S1—C2	1.813 (3)	C6—H6	0.950
S1—C3	1.732 (3)	C7—C8	1.329 (4)
O1—C5	1.361 (3)	C7—H7	0.950
O1—C8	1.364 (3)	C8—H8	0.950
N1—N2	1.400 (3)	C9—C10	1.395 (3)
N1—C4	1.310 (3)	C9—C14	1.390 (3)
N2—C3	1.301 (3)	C10—C11	1.375 (4)
N3—N4	1.388 (2)	C10—H10	0.950
N3—C3	1.367 (3)	C11—C12	1.387 (4)
N3—C4	1.371 (3)	C11—H11	0.950
N4—C1	1.293 (3)	C12—C13	1.376 (3)
C1—C2	1.505 (3)	C12—C15	1.506 (4)
C1—C9	1.475 (3)	C13—C14	1.382 (3)
C2—H21	1.004	C13—H13	0.950
C2—H22	0.969	C14—H14	0.950
C4—C5	1.441 (3)	C15—H151	0.950
C5—C6	1.344 (3)	C15—H152	0.950
C6—C7	1.417 (4)	C15—H153	0.950
C2—S1—C3	94.0 (1)	N3—C4—C5	123.6 (2)
C5—O1—C8	106.1 (2)	O1—C5—C4	114.8 (2)
N2—N1—C4	107.6 (2)	O1—C5—C6	110.0 (2)
N1—N2—C3	106.8 (2)	C4—C5—C6	135.1 (2)
N4—N3—C3	129.2 (2)	C5—C6—C7	106.7 (2)
N4—N3—C4	125.0 (2)	C5—C6—H6	126.2
C3—N3—C4	105.0 (2)	C7—C6—H6	127.1
N3—N4—C1	115.7 (2)	C6—C7—C8	106.5 (2)
N4—C1—C2	122.7 (2)	C6—C7—H7	126.5
N4—C1—C9	116.2 (2)	C8—C7—H7	127.0
C2—C1—C9	121.0 (2)	O1—C8—C7	110.7 (3)
S1—C2—C1	111.9 (2)	O1—C8—H8	124.7
S1—C2—H21	106.9	C7—C8—H8	124.6
S1—C2—H22	105.2	C1—C9—C10	120.7 (2)
C1—C2—H21	110.5	C1—C9—C14	121.8 (2)
C1—C2—H22	114.2	C10—C9—C14	117.5 (2)
H21—C2—H22	107.8	C9—C10—C11	120.7 (2)
S1—C3—N2	129.4 (2)	C9—C10—H10	119.2
S1—C3—N3	119.7 (2)	C11—C10—H10	120.1
N2—C3—N3	110.8 (2)	C10—C11—C12	121.9 (2)
N1—C4—N3	109.7 (2)	C10—C11—H11	119.3
N1—C4—C5	126.5 (2)	C12—C11—H11	118.8
C11—C12—C13	117.2 (2)	C13—C14—H14	119.9
C11—C12—C15	121.3 (2)	C12—C15—H151	109.4
C13—C12—C15	121.5 (2)	C12—C15—H152	109.4
C12—C13—C14	121.9 (2)	C12—C15—H153	109.6
C12—C13—H13	118.7	H151—C15—H152	109.5
C14—C13—H13	119.4	H151—C15—H153	109.5
C9—C14—C13	120.8 (2)	H152—C15—H153	109.5
C9—C14—H14	119.3
C3—S1—C2—C1	−52.0 (2)	N3—C4—C5—O1	−160.9 (2)
C3—S1—C2—H21	69.1	N3—C4—C5—C6	14.4 (5)
C3—S1—C2—H22	−176.6	O1—C5—C6—C7	−0.2 (3)
C2—S1—C3—N2	−151.8 (3)	O1—C5—C6—H6	179.9
C2—S1—C3—N3	28.9 (2)	C4—C5—C6—C7	−175.8 (3)
C8—O1—C5—C4	176.4 (2)	C4—C5—C6—H6	4.4
C8—O1—C5—C6	−0.1 (3)	C5—C6—C7—C8	0.5 (3)
C5—O1—C8—C7	0.4 (3)	C5—C6—C7—H7	−179.3
C5—O1—C8—H8	−179.6	H6—C6—C7—C8	−179.7
C4—N1—N2—C3	−0.1 (3)	H6—C6—C7—H7	0.5
N2—N1—C4—N3	−0.6 (3)	C6—C7—C8—O1	−0.5 (4)
N2—N1—C4—C5	−175.3 (2)	C6—C7—C8—H8	179.4
N1—N2—C3—S1	−178.6 (2)	H7—C7—C8—O1	179.3
N1—N2—C3—N3	0.8 (3)	H7—C7—C8—H8	−0.8
C3—N3—N4—C1	−26.7 (3)	C1—C9—C10—C11	175.9 (2)
C4—N3—N4—C1	164.9 (2)	C1—C9—C10—H10	−3.5
N4—N3—C3—S1	8.2 (4)	C14—C9—C10—C11	−1.8 (4)
N4—N3—C3—N2	−171.3 (2)	C14—C9—C10—H10	178.7
C4—N3—C3—S1	178.3 (2)	C1—C9—C14—C13	−176.4 (2)
C4—N3—C3—N2	−1.1 (3)	C1—C9—C14—H14	3.8
N4—N3—C4—N1	171.8 (2)	C10—C9—C14—C13	1.4 (3)
N4—N3—C4—C5	−13.4 (4)	C10—C9—C14—H14	−178.4
C3—N3—C4—N1	1.1 (3)	C9—C10—C11—C12	0.6 (4)
C3—N3—C4—C5	175.9 (2)	C9—C10—C11—H11	−179.9
N3—N4—C1—C2	−5.5 (3)	H10—C10—C11—C12	−179.9
N3—N4—C1—C9	178.6 (2)	H10—C10—C11—H11	−0.4
N4—C1—C2—S1	47.8 (3)	C10—C11—C12—C13	1.1 (4)
N4—C1—C2—H21	−71.2	C10—C11—C12—C15	−178.8 (2)
N4—C1—C2—H22	167.1	H11—C11—C12—C13	−178.5
C9—C1—C2—S1	−136.5 (2)	H11—C11—C12—C15	1.7
C9—C1—C2—H21	104.6	C11—C12—C13—C14	−1.5 (4)
C9—C1—C2—H22	−17.1	C11—C12—C13—H13	178.6
N4—C1—C9—C10	−11.2 (3)	C15—C12—C13—C14	178.3 (2)
N4—C1—C9—C14	166.5 (2)	C15—C12—C13—H13	−1.6
C2—C1—C9—C10	172.8 (2)	C12—C13—C14—C9	0.3 (4)
C2—C1—C9—C14	−9.5 (3)	C12—C13—C14—H14	−179.9
N1—C4—C5—O1	13.0 (4)	H13—C13—C14—C9	−179.9
N1—C4—C5—C6	−171.6 (3)	H13—C13—C14—H14	−0.0

(II)

Crystal data

C14H10N4OS	Z = 4
Mr = 282.33	Dx = 1.49 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.799 (2) Å	θ = 9.8–18.2°
b = 9.302 (1) Å	µ = 0.26 mm^−1
c = 15.5437 (1) Å	T = 295 K
β = 97.40 (1)°	Prismatic, yellow
V = 1261.6 (2) Å^3	0.60 × 0.42 × 0.18 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.018
ω/2θ scans	θmax = 26.3°
Absorption correction: empirical (using intensity measurements) via ψ scans (Fair, 1990)	h = −10→0
Tmin = 0.932, Tmax = 1.00	k = −11→0
2893 measured reflections	l = −19→19
2546 independent reflections	3 standard reflections every 120 min
1986 reflections with I > 2σ(I)	intensity decay: 0.6%

Refinement

Refinement on F	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ(F^2) + (0.02F)^2 + 1]
wR(F^2) = 0.042	(Δ/σ)max < 0.001
S = 0.74	Δρmax = 0.19 e Å^−3
1986 reflections	Δρmin = −0.29 e Å^−3
181 parameters

Special details

Refinement. In (I) and (II), H atoms were placed geometrically 0.95 Å from their parent atoms except for the H atoms of C2, which were found from Δρ maps and refined isotropically for a few cycles and then fixed.

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

	x	y	z	Uiso*/Ueq
S1	0.89590 (7)	0.18735 (7)	0.20244 (3)	0.0524 (2)
O1	1.3414 (2)	0.4792 (2)	−0.0218 (1)	0.0570 (5)
N1	1.2241 (2)	0.4280 (2)	0.1376 (1)	0.0471 (5)
N2	1.1453 (2)	0.3673 (2)	0.2016 (1)	0.0503 (6)
N3	1.0381 (2)	0.2935 (2)	0.0735 (1)	0.0360 (4)
N4	0.9291 (2)	0.2432 (2)	0.0078 (1)	0.0361 (4)
C1	0.8490 (2)	0.1343 (2)	0.0281 (1)	0.0348 (5)
C2	0.8796 (2)	0.0584 (2)	0.1141 (1)	0.0427 (6)
C3	1.0355 (2)	0.2886 (2)	0.1614 (1)	0.0424 (6)
C4	1.1572 (2)	0.3840 (2)	0.0619 (1)	0.0375 (5)
C5	1.2036 (2)	0.4119 (2)	−0.0220 (1)	0.0379 (5)
C6	1.1443 (2)	0.3822 (3)	−0.1037 (1)	0.0504 (6)
C7	1.2492 (3)	0.4328 (3)	−0.1585 (2)	0.0525 (6)
C8	1.3652 (3)	0.4893 (3)	−0.1067 (2)	0.0582 (6)
C9	0.7270 (2)	0.0858 (2)	−0.0399 (1)	0.0351 (5)
C10	0.6663 (2)	0.1799 (2)	−0.1056 (1)	0.0464 (6)
C11	0.5557 (3)	0.1338 (3)	−0.1705 (1)	0.0527 (6)
C12	0.5046 (2)	−0.0071 (3)	−0.1725 (1)	0.0490 (6)
C13	0.5629 (3)	−0.0999 (2)	−0.1079 (2)	0.0515 (6)
C14	0.6721 (2)	−0.0544 (2)	−0.0414 (1)	0.0436 (6)
H6	1.049	0.336	−0.121	0.0646*
H7	1.238	0.428	−0.220	0.0671*
H8	1.453	0.531	−0.126	0.0747*
H10	0.703	0.276	−0.106	0.0595*
H11	0.513	0.199	−0.214	0.0684*
H12	0.430	−0.039	−0.218	0.0646*
H13	0.528	−0.197	−0.109	0.0659*
H14	0.710	−0.119	0.004	0.0570*
H21	0.977	0.005	0.118	0.0507*
H22	0.797	−0.004	0.125	0.0709*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0625 (3)	0.0603 (3)	0.0352 (2)	−0.0072 (3)	0.0092 (2)	−0.0008 (3)
O1	0.0462 (7)	0.066 (1)	0.0580 (8)	−0.0227 (7)	0.0033 (7)	−0.0066 (8)
N1	0.0495 (9)	0.0424 (9)	0.0463 (9)	−0.0038 (8)	−0.0062 (8)	−0.0037 (8)
N2	0.060 (1)	0.048 (1)	0.0398 (9)	−0.0036 (9)	−0.0049 (8)	−0.0061 (8)
N3	0.0363 (7)	0.0355 (8)	0.0346 (7)	−0.0019 (7)	−0.0017 (6)	−0.0012 (7)
N4	0.0362 (7)	0.0371 (8)	0.0337 (7)	−0.0034 (7)	−0.0010 (6)	−0.0012 (7)
C1	0.0350 (8)	0.0339 (9)	0.0358 (8)	0.0023 (8)	0.0056 (7)	−0.0005 (8)
C2	0.047 (1)	0.040 (1)	0.0404 (9)	−0.0023 (9)	0.0030 (8)	0.0050 (9)
C3	0.049 (1)	0.041 (1)	0.0358 (9)	0.0030 (9)	−0.0001 (8)	−0.0016 (9)
C4	0.0353 (9)	0.0290 (9)	0.046 (1)	0.0011 (8)	−0.0033 (8)	−0.0027 (8)
C5	0.0349 (9)	0.0284 (9)	0.049 (1)	−0.0024 (8)	0.0005 (8)	0.0002 (8)
C6	0.045 (1)	0.058 (1)	0.046 (1)	−0.016 (1)	−0.0022 (9)	0.003 (1)
C7	0.051 (1)	0.059 (1)	0.047 (1)	−0.011 (1)	0.0048 (9)	0.005 (1)
C8	0.054 (1)	0.063 (1)	0.059 (1)	−0.016 (1)	0.013 (1)	0.002 (1)
C9	0.0345 (8)	0.0341 (9)	0.0373 (8)	−0.0018 (8)	0.0072 (7)	−0.0031 (8)
C10	0.052 (1)	0.040 (1)	0.045 (1)	−0.009 (1)	−0.0027 (9)	0.0041 (9)
C11	0.058 (1)	0.051 (1)	0.046 (1)	−0.005 (1)	−0.005 (1)	0.003 (1)
C12	0.041 (1)	0.058 (1)	0.047 (1)	−0.006 (1)	0.0020 (9)	−0.014 (1)
C13	0.051 (1)	0.037 (1)	0.066 (1)	−0.009 (1)	0.006 (1)	−0.011 (1)
C14	0.047 (1)	0.032 (1)	0.052 (1)	0.0003 (9)	0.0066 (9)	−0.0002 (9)

Geometric parameters (Å, º)

S1—C2	1.815 (2)	C6—C7	1.415 (3)
S1—C3	1.733 (2)	C6—H6	0.950
O1—C5	1.364 (2)	C7—C8	1.325 (3)
O1—C8	1.365 (3)	C7—H7	0.950
N1—N2	1.403 (3)	C8—H8	0.950
N1—C4	1.311 (2)	C9—C10	1.397 (3)
N2—C3	1.306 (3)	C9—C14	1.390 (3)
N3—N4	1.389 (2)	C10—C11	1.377 (3)
N3—C3	1.369 (2)	C10—H10	0.950
N3—C4	1.374 (2)	C11—C12	1.385 (3)
N4—C1	1.296 (3)	C11—H11	0.950
C1—C2	1.506 (3)	C12—C13	1.372 (3)
C1—C9	1.477 (2)	C12—H12	0.950
C2—H21	0.989	C13—C14	1.384 (3)
C2—H22	0.960	C13—H13	0.950
C4—C5	1.439 (3)	C14—H14	0.950
C5—C6	1.338 (3)
C2—S1—C3	94.1 (1)	N3—C4—C5	122.7 (2)
C5—O1—C8	106.1 (2)	O1—C5—C4	115.9 (2)
N2—N1—C4	107.8 (2)	O1—C5—C6	109.5 (2)
N1—N2—C3	106.8 (2)	C4—C5—C6	134.5 (2)
N4—N3—C3	128.6 (2)	C5—C6—C7	107.3 (2)
N4—N3—C4	125.1 (2)	C5—C6—H6	126.2
C3—N3—C4	105.2 (2)	C7—C6—H6	126.5
N3—N4—C1	115.4 (1)	C6—C7—C8	106.1 (2)
N4—C1—C2	122.8 (2)	C6—C7—H7	126.9
N4—C1—C9	115.6 (2)	C8—C7—H7	127.0
C2—C1—C9	121.5 (2)	O1—C8—C7	111.0 (2)
S1—C2—C1	110.4 (1)	O1—C8—H8	124.6
S1—C2—H21	108.0	C7—C8—H8	124.5
S1—C2—H22	105.0	C1—C9—C10	120.3 (2)
C1—C2—H21	109.9	C1—C9—C14	121.2 (2)
C1—C2—H22	112.3	C10—C9—C14	118.5 (2)
H21—C2—H22	111.1	C9—C10—C11	120.5 (2)
S1—C3—N2	130.1 (2)	C9—C10—H10	119.5
S1—C3—N3	119.3 (1)	C11—C10—H10	120.0
N2—C3—N3	110.6 (2)	C10—C11—C12	120.5 (2)
N1—C4—N3	109.6 (2)	C10—C11—H11	119.8
N1—C4—C5	127.6 (2)	C12—C11—H11	119.7
C11—C12—C13	119.3 (2)	C14—C13—H13	119.6
C11—C12—H12	120.4	C9—C14—C13	120.3 (2)
C13—C12—H12	120.3	C9—C14—H14	119.6
C12—C13—C14	120.8 (2)	C13—C14—H14	120.1
C12—C13—H13	119.5
C3—S1—C2—C1	−53.8 (2)	N3—C4—C5—O1	−167.0 (2)
C3—S1—C2—H21	66.4	N3—C4—C5—C6	10.2 (4)
C3—S1—C2—H22	−175.1	O1—C5—C6—C7	0.1 (3)
C2—S1—C3—N2	−151.2 (2)	O1—C5—C6—H6	−179.7
C2—S1—C3—N3	29.5 (2)	C4—C5—C6—C7	−177.2 (2)
C8—O1—C5—C4	177.5 (2)	C4—C5—C6—H6	3.0
C8—O1—C5—C6	−0.3 (3)	C5—C6—C7—C8	0.2 (3)
C5—O1—C8—C7	0.5 (3)	C5—C6—C7—H7	−179.3
C5—O1—C8—H8	−179.4	H6—C6—C7—C8	−180.0
C4—N1—N2—C3	0.5 (2)	H6—C6—C7—H7	0.5
N2—N1—C4—N3	−1.2 (2)	C6—C7—C8—O1	−0.4 (3)
N2—N1—C4—C5	−176.1 (2)	C6—C7—C8—H8	179.4
N1—N2—C3—S1	−179.0 (2)	H7—C7—C8—O1	179.1
N1—N2—C3—N3	0.4 (2)	H7—C7—C8—H8	−1.1
C3—N3—N4—C1	−29.2 (3)	C1—C9—C10—C11	178.2 (2)
C4—N3—N4—C1	164.4 (2)	C1—C9—C10—H10	−1.3
N4—N3—C3—S1	9.9 (3)	C14—C9—C10—C11	−0.6 (3)
N4—N3—C3—N2	−169.5 (2)	C14—C9—C10—H10	−179.9
C4—N3—C3—S1	178.4 (1)	C1—C9—C14—C13	−176.9 (2)
C4—N3—C3—N2	−1.0 (2)	C1—C9—C14—H14	3.2
N4—N3—C4—N1	170.4 (2)	C10—C9—C14—C13	1.7 (3)
N4—N3—C4—C5	−14.4 (3)	C10—C9—C14—H14	−178.1
C3—N3—C4—N1	1.3 (2)	C9—C10—C11—C12	−1.1 (3)
C3—N3—C4—C5	176.6 (2)	C9—C10—C11—H11	178.3
N3—N4—C1—C2	−5.1 (3)	H10—C10—C11—C12	178.3
N3—N4—C1—C9	176.6 (2)	H10—C10—C11—H11	−2.3
N4—C1—C2—S1	49.2 (2)	C10—C11—C12—C13	1.5 (3)
N4—C1—C2—H21	−69.7	C10—C11—C12—H12	−178.4
N4—C1—C2—H22	166.1	H11—C11—C12—C13	−177.9
C9—C1—C2—S1	−132.6 (2)	H11—C11—C12—H12	2.2
C9—C1—C2—H21	108.5	C11—C12—C13—C14	−0.3 (3)
C9—C1—C2—H22	−15.8	C11—C12—C13—H13	179.8
N4—C1—C9—C10	−22.8 (3)	H12—C12—C13—C14	179.6
N4—C1—C9—C14	155.9 (2)	H12—C12—C13—H13	−0.3
C2—C1—C9—C10	158.9 (2)	C12—C13—C14—C9	−1.3 (3)
C2—C1—C9—C14	−22.4 (3)	C12—C13—C14—H14	178.5
N1—C4—C5—O1	7.3 (3)	H13—C13—C14—C9	178.6
N1—C4—C5—C6	−175.5 (2)	H13—C13—C14—H14	−1.6