Three tri­thia­diazepines and a tri­thia­triazepine

The structures of 6-nitro-1,3[lambda]⁴[delta]²,5,2,4-tri­thia­diazepine [C₂HN₃O₂S₃, (1)], 6,7-di­nitro-1,3[lambda]⁴[delta]²,5,2,4-tri­thia­diazepine [C₂N₄O₄S₃, (2)], 1,3[lambda]⁴[delta]²,5,2,4-tri­thia­diazepine-6,7-dicarbo­nitrile [C₄N₄S₃, (3)] and 7-acetyl-1,3[lambda]⁴[delta]²,5,2,4,6-tri­thia­triazepine [C₃H₃N₃OS₃, (4)] presented here include the most precise determinations of these seven-membered 10 [pi]-electron aromatic ring systems published to date. Both (2) and (3) are sited around crystallographic twofold axes with half a mol­ecule per asymmetric unit. Comparison with other published derivatives of these rings reveals the effect of substituents on bonding, conformations and inter­molecular inter­actions, including [pi]-stacking. The deformation density analysis of (2) is consistent with the expected bonding electron density from other theoretical and experimental studies.

Computing details

For all compounds, data collection: Nicolet R3m software; cell refinement: Nicolet R3m software; data reduction: Nicolet R3m software; program(s) used to solve structure: SHELXS83 (Sheldrick, 1983); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008).

(I) 6-Nitro-1,3,5,2,4-trithiadiazepine

Crystal data

C2HN3O2S3	F(000) = 784
Mr = 195.24	Dx = 1.962 Mg m^−3
Orthorhombic, Pbca	Melting point: 359 K
Hall symbol: -P 2ac 2ab	Cu Kα radiation, λ = 1.54178 Å
a = 8.794 (9) Å	Cell parameters from 10 reflections
b = 11.696 (7) Å	µ = 9.81 mm^−1
c = 12.854 (8) Å	T = 293 K
V = 1322.1 (18) Å^3	Plate, yellow
Z = 8	0.40 × 0.10 × 0.01 mm

Data collection

Nicolet R3m diffractometer	629 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 56.7°, θmin = 6.9°
Scintillation counter scans	h = 0→9
Absorption correction: analytical (SHELXS83; Sheldrick, 1983)	k = 0→12
Tmin = 0.880, Tmax = 0.990	l = 0→13
881 measured reflections	2 standard reflections every 50 reflections
881 independent reflections	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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.158	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.1072P)^2] where P = (Fo^2 + 2Fc^2)/3
881 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.53 e Å^−3
0 restraints	Δρmin = −0.48 e Å^−3

Special details

Experimental. Face indexed crystal

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	−0.0663 (2)	−0.09035 (14)	0.13731 (14)	0.0470 (6)
N2	−0.2319 (7)	−0.0443 (5)	0.1062 (5)	0.0495 (15)
S3	−0.30395 (19)	0.07568 (16)	0.08169 (15)	0.0526 (6)
N4	−0.2099 (6)	0.1884 (5)	0.0867 (4)	0.0494 (16)
S5	−0.0436 (2)	0.23629 (14)	0.10978 (14)	0.0458 (6)
C6	0.0799 (7)	0.1264 (6)	0.1373 (5)	0.0378 (16)
C7	0.0689 (7)	0.0101 (6)	0.1464 (5)	0.0406 (16)
H7	0.1628	−0.0223	0.1619	0.049*
N8	0.2318 (6)	0.1727 (5)	0.1537 (4)	0.0459 (14)
O9	0.2402 (6)	0.2788 (5)	0.1543 (4)	0.0641 (15)
O10	0.3411 (6)	0.1105 (5)	0.1663 (4)	0.0639 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0423 (11)	0.0352 (9)	0.0635 (12)	−0.0024 (8)	−0.0019 (8)	0.0024 (7)
N2	0.035 (3)	0.038 (3)	0.075 (4)	−0.004 (3)	0.003 (3)	−0.004 (3)
S3	0.0297 (9)	0.0560 (11)	0.0719 (14)	0.0017 (8)	−0.0037 (8)	−0.0007 (9)
N4	0.035 (3)	0.042 (3)	0.071 (4)	0.008 (3)	−0.004 (3)	0.010 (3)
S5	0.0387 (10)	0.0357 (9)	0.0629 (12)	0.0022 (8)	−0.0006 (8)	0.0029 (8)
C6	0.030 (3)	0.041 (4)	0.042 (4)	−0.004 (3)	−0.002 (3)	0.000 (3)
C7	0.030 (3)	0.045 (4)	0.048 (4)	0.006 (3)	0.003 (3)	−0.004 (3)
N8	0.038 (3)	0.046 (3)	0.054 (3)	−0.004 (3)	0.002 (3)	−0.001 (3)
O9	0.051 (3)	0.056 (3)	0.085 (4)	−0.022 (3)	−0.001 (3)	0.001 (3)
O10	0.034 (3)	0.067 (3)	0.091 (4)	0.004 (3)	−0.006 (3)	−0.005 (3)

Geometric parameters (Å, º)

S1—N2	1.603 (6)	C6—C7	1.369 (9)
S1—C7	1.676 (7)	C6—N8	1.457 (8)
N2—S3	1.572 (6)	C7—H7	0.9300
S3—N4	1.557 (6)	N8—O10	1.217 (7)
N4—S5	1.594 (6)	N8—O9	1.242 (7)
S5—C6	1.719 (7)
N2—S1—C7	115.3 (3)	N8—C6—S5	109.3 (5)
S3—N2—S1	135.7 (4)	C6—C7—S1	137.8 (5)
N4—S3—N2	122.2 (3)	C6—C7—H7	111.1
S3—N4—S5	142.4 (4)	S1—C7—H7	111.1
N4—S5—C6	110.8 (3)	O10—N8—O9	123.3 (6)
C7—C6—N8	115.0 (6)	O10—N8—C6	121.4 (6)
C7—C6—S5	135.7 (5)	O9—N8—C6	115.3 (6)
C7—S1—N2—S3	−0.5 (7)	S5—C6—C7—S1	−0.6 (13)
S1—N2—S3—N4	−1.4 (8)	N2—S1—C7—C6	2.3 (9)
N2—S3—N4—S5	0.7 (8)	C7—C6—N8—O10	5.4 (9)
S3—N4—S5—C6	1.4 (8)	S5—C6—N8—O10	−174.2 (5)
N4—S5—C6—C7	−1.9 (8)	C7—C6—N8—O9	−174.2 (6)
N4—S5—C6—N8	177.6 (4)	S5—C6—N8—O9	6.2 (7)
N8—C6—C7—S1	179.9 (5)

(II) 6,7-Dinitro-1,3,5,2,4-trithiadiazepine

Crystal data

C2N4O4S3	F(000) = 480
Mr = 240.24	Dx = 1.965 Mg m^−3
Monoclinic, I2/a	Melting point: 336 K
Hall symbol: -I 2ya	Cu Kα radiation, λ = 1.54178 Å
a = 11.182 (2) Å	Cell parameters from 11 reflections
b = 8.436 (2) Å	µ = 8.38 mm^−1
c = 8.609 (2) Å	T = 293 K
β = 91.36 (2)°	Block, yellow
V = 811.9 (3) Å^3	0.15 × 0.10 × 0.10 mm
Z = 4

Data collection

Nicolet R3m diffractometer	511 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 57.0°, θmin = 6.6°
Scintillation counter scans	h = −12→12
Absorption correction: analytical (SHELXS83; Sheldrick, 1983)	k = −9→0
Tmin = 0.380, Tmax = 0.470	l = 0→9
581 measured reflections	2 standard reflections every 50 reflections
543 independent reflections	intensity decay: 10%

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)] = 0.025	[1.00000 + 0.00000exp(0.00(sinθ/λ)^2)]/ [σ^2(Fo^2) + 0.0000 + 0.7454*P + (0.0347P)^2 + 1.0000sinθ/λ] where P = 0.33333Fo^2 + 0.66667Fc^2
wR(F^2) = 0.066	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.23 e Å^−3
543 reflections	Δρmin = −0.16 e Å^−3
61 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0022 (2)

Special details

Experimental. Face indexed crystal

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	0.10938 (6)	0.64585 (8)	0.36973 (8)	0.0492 (3)
N2	0.1492 (2)	0.4698 (3)	0.4119 (3)	0.0599 (7)
S3	0.2500	0.37959 (11)	0.5000	0.0660 (4)
C7	0.1998 (2)	0.7874 (3)	0.4541 (2)	0.0357 (6)
N8	0.14231 (16)	0.9410 (2)	0.4163 (2)	0.0433 (5)
O9	0.10665 (18)	0.9583 (2)	0.2816 (2)	0.0673 (6)
O10	0.12905 (16)	1.0365 (2)	0.5196 (2)	0.0551 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0408 (4)	0.0517 (5)	0.0547 (5)	−0.0108 (3)	−0.0089 (3)	−0.0057 (3)
N2	0.0622 (15)	0.0451 (13)	0.0722 (16)	−0.0152 (11)	0.0006 (12)	−0.0088 (11)
S3	0.0765 (8)	0.0367 (6)	0.0850 (8)	0.000	0.0084 (6)	0.000
C7	0.0298 (11)	0.0384 (13)	0.0387 (12)	−0.0015 (10)	−0.0003 (9)	0.0007 (10)
N8	0.0276 (11)	0.0470 (12)	0.0550 (13)	0.0019 (9)	−0.0029 (9)	0.0073 (11)
O9	0.0602 (13)	0.0791 (15)	0.0618 (13)	0.0192 (10)	−0.0139 (9)	0.0180 (10)
O10	0.0441 (11)	0.0437 (11)	0.0773 (13)	0.0072 (8)	−0.0007 (9)	−0.0072 (10)

Geometric parameters (Å, º)

S1—N2	1.590 (2)	C7—C7^i	1.359 (4)
S1—C7	1.715 (2)	C7—N8	1.479 (3)
N2—S3	1.544 (3)	N8—O10	1.212 (3)
S3—N2^i	1.544 (3)	N8—O9	1.226 (3)
N2—S1—C7	113.24 (12)	N8—C7—S1	105.59 (15)
S3—N2—S1	140.36 (16)	O10—N8—O9	124.9 (2)
N2^i—S3—N2	120.91 (17)	O10—N8—C7	118.76 (19)
C7^i—C7—N8	118.47 (11)	O9—N8—C7	116.2 (2)
C7^i—C7—S1	135.85 (8)
C7—S1—N2—S3	−4.5 (3)	C7^i—C7—N8—O10	−45.2 (3)
S1—N2—S3—N2^i	3.01 (19)	S1—C7—N8—O10	131.85 (18)
N2—S1—C7—C7^i	2.2 (4)	C7^i—C7—N8—O9	138.0 (3)
N2—S1—C7—N8	−174.10 (15)	S1—C7—N8—O9	−44.9 (2)

Symmetry code: (i) −x+1/2, y, −z+1.

(III) 1,3,5,2,4-Trithiadiazepine-6,7-dicarbonitrile

Crystal data

C4N4S3	F(000) = 400
Mr = 200.26	Dx = 1.853 Mg m^−3
Orthorhombic, Pbcn	Melting point: 413 K
Hall symbol: -P 2n 2ab	Cu Kα radiation, λ = 1.54178 Å
a = 3.897 (1) Å	Cell parameters from 9 reflections
b = 16.881 (9) Å	µ = 8.90 mm^−1
c = 10.910 (4) Å	T = 293 K
V = 717.7 (5) Å^3	Needle, orange
Z = 4	0.16 × 0.06 × 0.04 mm

Data collection

Nicolet R3m diffractometer	338 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 56.9°, θmin = 5.2°
scintillation counter scans	h = 0→4
Absorption correction: analytical (SHELXS83; Sheldrick, 1983)	k = 0→18
Tmin = 0.560, Tmax = 0.740	l = −11→0
489 measured reflections	2 standard reflections every 50 reflections
489 independent reflections	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)] = 0.042	w = 1/[σ^2(Fo^2) + (0.0464P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.094	(Δ/σ)max < 0.001
S = 0.96	Δρmax = 0.28 e Å^−3
489 reflections	Δρmin = −0.30 e Å^−3
52 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0002 (3)

Special details

Experimental. Face indexed crystal

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
S1	0.2674 (4)	0.34164 (7)	0.90311 (10)	0.0403 (5)
N2	0.3388 (12)	0.2532 (2)	0.8586 (4)	0.0442 (14)
S3	0.5000	0.20707 (10)	0.7500	0.0481 (7)
C7	0.4141 (14)	0.4138 (3)	0.8051 (4)	0.0340 (13)
C8	0.3196 (14)	0.4895 (3)	0.8555 (4)	0.0368 (14)
N9	0.2370 (15)	0.5483 (3)	0.8960 (4)	0.0557 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0560 (9)	0.0319 (7)	0.0329 (7)	0.0010 (8)	0.0069 (8)	0.0016 (6)
N2	0.064 (4)	0.028 (2)	0.041 (2)	−0.001 (2)	0.007 (3)	0.0015 (19)
S3	0.0704 (16)	0.0270 (9)	0.0469 (11)	0.000	0.0076 (13)	0.000
C7	0.045 (3)	0.030 (2)	0.028 (2)	0.000 (3)	−0.009 (3)	−0.002 (2)
C8	0.049 (4)	0.033 (3)	0.029 (3)	0.001 (3)	−0.004 (3)	0.002 (2)
N9	0.079 (4)	0.042 (3)	0.046 (3)	0.020 (3)	−0.006 (3)	−0.002 (2)

Geometric parameters (Å, º)

S1—N2	1.594 (4)	C7—C7^i	1.376 (9)
S1—C7	1.718 (5)	C7—C8	1.439 (7)
N2—S3	1.551 (4)	C8—N9	1.133 (6)
S3—N2^i	1.551 (4)
N2—S1—C7	114.6 (2)	C7^i—C7—S1	134.87 (16)
S3—N2—S1	140.7 (3)	C8—C7—S1	107.8 (3)
N2—S3—N2^i	119.7 (3)	N9—C8—C7	178.2 (7)
C7^i—C7—C8	117.3 (3)
C7—S1—N2—S3	−1.2 (6)	N2—S1—C7—C7^i	−0.8 (9)
S1—N2—S3—N2^i	1.0 (4)	N2—S1—C7—C8	177.9 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

(IV) 7-Acetyl-1,3,5,2,4,6-trithiatriazene

Crystal data

C3H3N3OS3	F(000) = 392
Mr = 193.26	Dx = 1.766 Mg m^−3
Monoclinic, P21/c	Melting point: 325 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 8.647 (3) Å	Cell parameters from 12 reflections
b = 5.862 (1) Å	µ = 8.81 mm^−1
c = 14.674 (4) Å	T = 293 K
β = 102.21 (3)°	Block, yellow
V = 727.0 (3) Å^3	0.20 × 0.15 × 0.15 mm
Z = 4

Data collection

Nicolet R3m diffractometer	743 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.107
Graphite monochromator	θmax = 50.0°, θmin = 5.2°
scintillation counter scans	h = 0→8
Absorption correction: analytical (SHELXS83; Sheldrick, 1983)	k = 0→5
Tmin = 0.170, Tmax = 0.340	l = −14→14
812 measured reflections	2 standard reflections every 50 reflections
756 independent reflections	intensity decay: 7%

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)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0697P)^2 + 0.6145P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max = 0.007
756 reflections	Δρmax = 0.25 e Å^−3
93 parameters	Δρmin = −0.42 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.074 (5)

Special details

Experimental. Face indexed crystal

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	0.19281 (12)	0.66362 (19)	0.69467 (7)	0.0459 (6)
N2	0.0113 (5)	0.7256 (6)	0.6931 (3)	0.0464 (10)
S3	−0.15819 (12)	0.63759 (18)	0.65274 (8)	0.0465 (6)
N4	−0.1829 (4)	0.4174 (6)	0.5923 (2)	0.0448 (10)
S5	−0.06689 (12)	0.23333 (17)	0.56068 (7)	0.0437 (6)
N6	0.1163 (4)	0.2709 (5)	0.5892 (2)	0.0404 (9)
C7	0.2172 (4)	0.4166 (7)	0.6348 (3)	0.0377 (10)
C8	0.3897 (5)	0.3801 (8)	0.6374 (3)	0.0497 (12)
C9	0.4370 (5)	0.1692 (9)	0.5945 (4)	0.0621 (14)
H9A	0.5504	0.1592	0.6068	0.093*
H9B	0.3963	0.1731	0.5284	0.093*
H9C	0.3951	0.0387	0.6206	0.093*
O10	0.4841 (4)	0.5238 (7)	0.6742 (3)	0.0762 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0418 (9)	0.0408 (9)	0.0533 (9)	−0.0069 (5)	0.0063 (6)	−0.0117 (5)
N2	0.047 (2)	0.035 (2)	0.057 (2)	−0.0019 (15)	0.0114 (16)	−0.0052 (17)
S3	0.0410 (8)	0.0420 (9)	0.0559 (9)	0.0037 (5)	0.0091 (5)	−0.0005 (5)
N4	0.0357 (19)	0.048 (2)	0.049 (2)	−0.0015 (16)	0.0052 (15)	0.0040 (17)
S5	0.0404 (8)	0.0370 (9)	0.0512 (9)	−0.0070 (4)	0.0040 (5)	−0.0053 (4)
N6	0.040 (2)	0.035 (2)	0.0465 (19)	0.0006 (16)	0.0106 (16)	−0.0023 (16)
C7	0.039 (2)	0.033 (2)	0.040 (2)	−0.0025 (19)	0.0054 (18)	−0.0021 (18)
C8	0.040 (3)	0.053 (3)	0.056 (3)	−0.001 (2)	0.010 (2)	−0.003 (2)
C9	0.044 (3)	0.062 (3)	0.079 (3)	0.011 (2)	0.010 (2)	−0.011 (3)
O10	0.0414 (19)	0.074 (3)	0.113 (3)	−0.0149 (18)	0.0159 (18)	−0.031 (2)

Geometric parameters (Å, º)

S1—N2	1.606 (4)	C7—C8	1.499 (6)
S1—C7	1.729 (4)	C8—O10	1.217 (5)
N2—S3	1.548 (4)	C8—C9	1.483 (7)
S3—N4	1.555 (4)	C9—H9A	0.9600
N4—S5	1.607 (4)	C9—H9B	0.9600
S5—N6	1.566 (4)	C9—H9C	0.9600
N6—C7	1.301 (5)
N2—S1—C7	113.93 (18)	O10—C8—C9	123.1 (4)
S3—N2—S1	140.7 (2)	O10—C8—C7	118.8 (4)
N2—S3—N4	119.95 (19)	C9—C8—C7	118.1 (4)
S3—N4—S5	134.7 (2)	C8—C9—H9A	109.5
N6—S5—N4	119.12 (18)	C8—C9—H9B	109.5
C7—N6—S5	139.5 (3)	H9A—C9—H9B	109.5
N6—C7—C8	118.3 (4)	C8—C9—H9C	109.5
N6—C7—S1	132.1 (3)	H9A—C9—H9C	109.5
C8—C7—S1	109.6 (3)	H9B—C9—H9C	109.5
C7—S1—N2—S3	−1.5 (5)	N2—S1—C7—N6	−0.4 (5)
S1—N2—S3—N4	0.3 (5)	N2—S1—C7—C8	177.7 (3)
N2—S3—N4—S5	3.1 (4)	N6—C7—C8—O10	174.9 (4)
S3—N4—S5—N6	−3.4 (4)	S1—C7—C8—O10	−3.5 (5)
N4—S5—N6—C7	0.1 (5)	N6—C7—C8—C9	−5.1 (6)
S5—N6—C7—C8	−176.2 (3)	S1—C7—C8—C9	176.5 (3)
S5—N6—C7—S1	1.8 (7)