2-[2-Methyl-5-nitro-4-(phenyl­sulfonyl­methyl)­imidazol-1-yl]­ethanol and 2-methyl-5-nitro-4-phenyl­sulfonyl­methyl-1,3-thia­zole

The title compounds, C₁₃H₁₅N₃O₅S and C₁₁H₁₀N₂O₄S₂, respectively, both contain a phenyl­sulfonyl group connected, through a methyl­ene bridge, to either a substituted nitro­imidazole or nitro-1,3-thia­zole ring. In the imidazole-containing mol­ecule, the nitro and sulfonyl groups are trans relative to the sulfonyl-methyl bond, while in the thia­zole-containing mol­ecule, these substituents are cis. The stabilizing interactions within the crystals are also different between the two compounds.

S1. Comment

5-Nitroimidazoles and 5-nitrothiazoles are useful compounds with regard to their biological activities (Nair & Nagarajan, 1983; Kawashima et al., 2001; Andreani et al., 2001). We previously showed that sulfones are relevant synthons in the preparation of new 4-substituted-5-nitroheterocycles (Crozet et al., 2002). In this paper, we describe the X-ray structures of 2-(4-benzenesulfonylmethyl-2-methyl-5-nitroimidazol-1-yl)ethanol, (I) and 4-benzenesulfonylmethyl-2-methyl-5-nitrothiazole, (II), which are, to our knowledge, the first examples of benzenesulfonylmethyl–nitro heterocyclic compounds structurally characterized by single-crystal X-ray diffraction.

In both (I) and (II), the nitro group is almost coplanar with the heterocyclic ring; the angles between NO₂ and the mean five-membered-ring plane are 4.2 (3) and 6.7 (1)° for (I) and (II), respectively. The distances and angles involving the various heteroatoms (Tables 1 and 3) are comparable to those observed in other phenylsulfonyl compounds containing a heterocycle (De Bondt et al., 1993; Govindamasamy et al., 1998; SethuSankar et al., 2002).

Comparison of the structures of (I) and (II) reveals a difference in the relative position of the six- and five-membered rings relative to each other. In (I), the phenyl is oriented in the same direction as the nitro group on the imidazole ring, while, in (II), it is oriented in the same direction as the C11 methyl group (Figs. 1 and 2). Looking at this another way,, in (I), the nitro and sulfonyl substituents are trans relative to one another, while in (II), they are cis, with the O atoms pointing in the same direction; the dihedral angles between the planes defined by NO₂ and SO₂ are 157.1 (2) and 47.6 (2)° in (I) and (II), respectively. To complement this description, for each molecule, we defined the bisector of the NO₂ and SO₂ planes, translated these vectors to a common origin and calculated the angle between them; the values are 134.52 and 40.88% for (I) and (II), respectively, and could be considered as convenient descriptors of the relative orientation of such groups in flexible systems similar to the title compounds. This difference in conformation between the two structures is probably due to the presence of the hydroxyethyl group on the imidazole ring in (I). Indeed, the hydroxyl group is oriented trans relatively to the heterocycle; the torsion angle N2—C12—C13—O5 is -173.9 (2)°. This involves the hydroxyl group in a hydrogen bond with atom N1ⁱ of a molecule of an adjacent cell [symmetry code: (I) x, y + 1, z]; the H5b···N1ⁱ distance is 2.07 Å and the O5—H5b···N1ⁱ angle is 161.9° (Table 2). This hydrogen bond organizes the molecules of (I) within the crystal into an infinite molecular chain parallel to the b axis. Finally, the closed conformation adopted by (I) tends to position the two rings in such a way that they can accommodate a weak C—H···π interaction; the distance between the centroid of the imidazole ring and atom H6 on C6 is 3.26 Å and the C6—H6···centroid angle is 117.6°, which are in the range observed for classical C—H···π interactions (Takahashi et al., 2000).

In compound (II), only an intermolecular C—H···π interaction can be found, between the thiazole ring and the phenyl ring of a molecule of an adjacent cell; the distance between atom H11f on C11 and the centroid of the plane C1ⁱⁱ/C2ⁱⁱ/C3ⁱⁱ/C4ⁱⁱ/C5ⁱⁱ/C6ⁱⁱ is 2.95 Å [symmetry code: (ii) x + 1/2, -y + 3/2, z - 1/2], whereas the C11—H11f···centroid angle is 165.3°. A careful look at the packing of the molecules also shows that both compounds are not stabilized in the same way within the crystal. For (I), we can observe two intermolecular π–π stackings involving the aromatic cycles; the distance between the centroids of the imidazole ring and the centroid of a phenyl ring of a symmetry-related molecule (symmetry code: x, -y + 1/2, z + 1/2) is 3.481 (1) Å and the dihedral between the planes is 6.01°; the distance between the centroid of the phenyl ring and the centroid of the phenyl ring of a molecule in an adjacent cell (symmetry code: -x, 1 - y, -z) is 4.872 (1) Å, with a dihedral of 0.03° between the two planes. In compound (II), no such clear interactions can be found; the shortest distances between the various rings of symmetry-related molecules range from 4.336 (1) to 5.253 (1) Å, with dihedral angles ranging from 17.4 to 21.6°.

S2. Experimental

2-(4-Benzenesulfonylmethyl-2-methyl-5-nitroimidazol-1-yl)ethanol, (I), was prepared by the vicarious nucleophilic substitution of hydrogen (VNS) method (Makosza & Kwast, 1987) from 2-(2-methyl-5-nitroimidazol-1-yl)ethanol with chloromethyl phenyl sulfone. 4-Benzenesulfonylmethyl-2-methyl-5-nitrothiazole, (II), was prepared from 4-chloromethyl-2-methyl-5-nitrothiazole and sodium benzenesulfinate via an SRN1 reaction (Gellis et al., 1997). Suitable crystals of (I) and (II) were grown by slow evaporation from chloroform solutions at room temperature.

S3. Refinement

Most of the H atoms, particularly the H atoms of the hydroxyethyl group of (I), were found through the final difference Fourier map. They were introduced in calculated positions, but were constrained to their parent atom during the refinement. Disordered H atoms were detected on atom C11 in (II).

Computing details

For both compounds, data collection: KappaCCD Reference Manual (Nonius, 1998); cell refinement: KappaCCD Reference; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. An ORTEPII (Johnson, 1976) view of compound (I), showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. An ORTEPII (Johnson, 1976) view of compound (II), showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.

(I) 2-(4-benzenesulfonylmethyl-2-methyl-5-nitro-imidazol-1-yl)-ethanol

Crystal data

C13H15N3O5S	F(000) = 680
Mr = 325.34	Dx = 1.484 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2911 reflections
a = 12.5976 (3) Å	θ = 2.4–26.4°
b = 7.7874 (3) Å	µ = 0.25 mm^−1
c = 14.8929 (5) Å	T = 293 K
β = 94.427 (2)°	Prism, colorless
V = 1456.67 (8) Å^3	0.6 × 0.5 × 0.4 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2509 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
Graphite monochromator	θmax = 26.4°, θmin = 2.4°
ϕ scans	h = 0→14
2911 measured reflections	k = 0→9
2726 independent reflections	l = −18→18

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) = 0.113	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0359P)^2 + 0.6408P] where P = (Fo^2 + 2Fc^2)/3
2726 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.28 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
S1	0.21423 (4)	0.02005 (6)	0.10308 (3)	0.05482 (19)
O1	0.14467 (15)	−0.10385 (19)	0.05876 (12)	0.0865 (6)
O2	0.32604 (12)	−0.0151 (2)	0.11349 (11)	0.0763 (5)
O3	0.15023 (17)	0.6036 (2)	0.28117 (17)	0.1074 (7)
O4	0.06922 (12)	0.3935 (2)	0.21328 (12)	0.0743 (5)
O5	0.45589 (12)	0.80584 (17)	0.33634 (13)	0.0762 (5)
H5B	0.4093	0.8795	0.3350	0.114*
N1	0.32903 (10)	0.10909 (16)	0.31418 (9)	0.0388 (3)
N2	0.31723 (11)	0.38808 (16)	0.34262 (8)	0.0392 (3)
N3	0.14515 (13)	0.4535 (2)	0.25888 (11)	0.0540 (4)
C1	0.19509 (13)	0.2181 (2)	0.04813 (11)	0.0461 (4)
C2	0.10579 (15)	0.2396 (3)	−0.01101 (12)	0.0520 (4)
H2	0.0578	0.1499	−0.0221	0.062*
C3	0.08906 (17)	0.3957 (3)	−0.05324 (13)	0.0602 (5)
H3	0.0304	0.4108	−0.0943	0.072*
C4	0.15864 (19)	0.5290 (3)	−0.03497 (15)	0.0656 (6)
H4	0.1457	0.6349	−0.0626	0.079*
C5	0.24722 (18)	0.5075 (3)	0.02373 (15)	0.0634 (5)
H5	0.2936	0.5990	0.0357	0.076*
C6	0.26790 (14)	0.3511 (3)	0.06516 (12)	0.0527 (4)
H6	0.3289	0.3349	0.1035	0.063*
C7	0.16892 (14)	0.0505 (2)	0.21300 (13)	0.0491 (4)
H7A	0.0972	0.0966	0.2071	0.059*
H7B	0.1663	−0.0600	0.2429	0.059*
C8	0.23837 (12)	0.1683 (2)	0.26970 (10)	0.0374 (3)
C9	0.37456 (12)	0.2425 (2)	0.35730 (10)	0.0377 (3)
C10	0.22990 (12)	0.3413 (2)	0.28604 (10)	0.0386 (3)
C11	0.47418 (15)	0.2306 (2)	0.41651 (12)	0.0519 (4)
H11A	0.5009	0.1152	0.4158	0.078*
H11B	0.4601	0.2613	0.4769	0.078*
H11C	0.5262	0.3077	0.3952	0.078*
C12	0.35328 (16)	0.5592 (2)	0.37392 (12)	0.0510 (4)
H12A	0.3999	0.5475	0.4285	0.061*
H12B	0.2922	0.6273	0.3879	0.061*
C13	0.41195 (17)	0.6501 (2)	0.30297 (14)	0.0555 (5)
H13A	0.4684	0.5766	0.2843	0.067*
H13B	0.3632	0.6729	0.2507	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0532 (3)	0.0423 (3)	0.0657 (3)	0.01013 (18)	−0.0171 (2)	−0.01797 (19)
O1	0.1042 (13)	0.0465 (8)	0.1007 (12)	−0.0015 (8)	−0.0432 (10)	−0.0254 (8)
O2	0.0625 (9)	0.0831 (11)	0.0809 (10)	0.0370 (8)	−0.0100 (7)	−0.0232 (8)
O3	0.1008 (14)	0.0509 (10)	0.164 (2)	0.0333 (9)	−0.0323 (13)	−0.0187 (11)
O4	0.0509 (8)	0.0752 (10)	0.0934 (11)	0.0187 (7)	−0.0154 (7)	0.0023 (8)
O5	0.0624 (9)	0.0306 (6)	0.1301 (14)	−0.0031 (6)	−0.0278 (9)	0.0022 (7)
N1	0.0364 (7)	0.0323 (6)	0.0470 (7)	−0.0025 (5)	−0.0023 (5)	0.0057 (5)
N2	0.0457 (7)	0.0336 (7)	0.0384 (6)	−0.0020 (5)	0.0035 (5)	−0.0010 (5)
N3	0.0510 (9)	0.0498 (9)	0.0612 (9)	0.0154 (7)	0.0040 (7)	0.0040 (7)
C1	0.0408 (9)	0.0523 (10)	0.0450 (8)	0.0059 (7)	0.0017 (7)	−0.0127 (7)
C2	0.0446 (9)	0.0609 (11)	0.0495 (9)	0.0043 (8)	−0.0036 (7)	−0.0098 (8)
C3	0.0574 (11)	0.0756 (14)	0.0474 (10)	0.0159 (10)	0.0036 (8)	0.0003 (9)
C4	0.0770 (15)	0.0629 (13)	0.0592 (11)	0.0081 (11)	0.0192 (10)	0.0068 (9)
C5	0.0643 (13)	0.0629 (12)	0.0648 (12)	−0.0115 (10)	0.0172 (10)	−0.0032 (10)
C6	0.0430 (9)	0.0652 (12)	0.0504 (9)	−0.0016 (8)	0.0061 (7)	−0.0118 (8)
C7	0.0393 (9)	0.0403 (9)	0.0656 (11)	−0.0074 (7)	−0.0087 (7)	0.0054 (8)
C8	0.0340 (7)	0.0356 (8)	0.0424 (8)	−0.0026 (6)	0.0016 (6)	0.0061 (6)
C9	0.0383 (8)	0.0350 (7)	0.0395 (7)	−0.0043 (6)	0.0015 (6)	0.0049 (6)
C10	0.0386 (8)	0.0376 (8)	0.0398 (7)	0.0042 (6)	0.0042 (6)	0.0033 (6)
C11	0.0452 (9)	0.0515 (10)	0.0567 (10)	−0.0084 (8)	−0.0106 (8)	0.0038 (8)
C12	0.0676 (12)	0.0363 (8)	0.0486 (9)	−0.0016 (8)	0.0010 (8)	−0.0105 (7)
C13	0.0646 (12)	0.0317 (8)	0.0695 (12)	−0.0049 (8)	0.0005 (9)	0.0020 (8)

Geometric parameters (Å, º)

S1—O1	1.4300 (15)	C3—H3	0.9300
S1—O2	1.4314 (15)	C4—C5	1.374 (3)
S1—C1	1.7537 (19)	C4—H4	0.9300
S1—C7	1.791 (2)	C5—C6	1.381 (3)
O3—N3	1.215 (2)	C5—H5	0.9300
O4—N3	1.222 (2)	C6—H6	0.9300
O5—C13	1.408 (2)	C7—C8	1.486 (2)
O5—H5B	0.8200	C7—H7A	0.9700
N1—C9	1.328 (2)	C7—H7B	0.9700
N1—C8	1.3562 (19)	C8—C10	1.374 (2)
N2—C9	1.353 (2)	C9—C11	1.480 (2)
N2—C10	1.382 (2)	C11—H11A	0.9600
N2—C12	1.472 (2)	C11—H11B	0.9600
N3—C10	1.415 (2)	C11—H11C	0.9600
C1—C2	1.384 (2)	C12—C13	1.511 (3)
C1—C6	1.394 (3)	C12—H12A	0.9700
C2—C3	1.377 (3)	C12—H12B	0.9700
C2—H2	0.9300	C13—H13A	0.9700
C3—C4	1.373 (3)	C13—H13B	0.9700
O1—S1—O2	118.94 (10)	C8—C7—H7A	109.0
O1—S1—C1	108.70 (9)	S1—C7—H7A	109.0
O2—S1—C1	108.49 (10)	C8—C7—H7B	109.0
O1—S1—C7	106.50 (11)	S1—C7—H7B	109.0
O2—S1—C7	107.86 (9)	H7A—C7—H7B	107.8
C1—S1—C7	105.56 (8)	N1—C8—C10	108.71 (13)
C13—O5—H5B	109.5	N1—C8—C7	120.29 (14)
C9—N1—C8	106.62 (13)	C10—C8—C7	130.98 (15)
C9—N2—C10	105.50 (12)	N1—C9—N2	111.85 (13)
C9—N2—C12	124.03 (14)	N1—C9—C11	123.64 (15)
C10—N2—C12	130.06 (14)	N2—C9—C11	124.48 (15)
O3—N3—O4	122.80 (17)	C8—C10—N2	107.30 (13)
O3—N3—C10	119.58 (17)	C8—C10—N3	128.49 (15)
O4—N3—C10	117.62 (16)	N2—C10—N3	123.98 (15)
C2—C1—C6	121.13 (18)	C9—C11—H11A	109.5
C2—C1—S1	118.62 (15)	C9—C11—H11B	109.5
C6—C1—S1	120.25 (14)	H11A—C11—H11B	109.5
C3—C2—C1	119.04 (19)	C9—C11—H11C	109.5
C3—C2—H2	120.5	H11A—C11—H11C	109.5
C1—C2—H2	120.5	H11B—C11—H11C	109.5
C4—C3—C2	120.29 (19)	N2—C12—C13	110.99 (14)
C4—C3—H3	119.9	N2—C12—H12A	109.4
C2—C3—H3	119.9	C13—C12—H12A	109.4
C3—C4—C5	120.6 (2)	N2—C12—H12B	109.4
C3—C4—H4	119.7	C13—C12—H12B	109.4
C5—C4—H4	119.7	H12A—C12—H12B	108.0
C4—C5—C6	120.5 (2)	O5—C13—C12	110.91 (17)
C4—C5—H5	119.7	O5—C13—H13A	109.5
C6—C5—H5	119.7	C12—C13—H13A	109.5
C5—C6—C1	118.38 (18)	O5—C13—H13B	109.5
C5—C6—H6	120.8	C12—C13—H13B	109.5
C1—C6—H6	120.8	H13A—C13—H13B	108.0
C8—C7—S1	112.71 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···N1^i	0.82	2.07	2.8562 (19)	162

Symmetry code: (i) x, y+1, z.

(II) 4-benzenesulfonylmethyl-2-methyl-5-nitro-thiazole

Crystal data

C11H10N2O4S2	F(000) = 616
Mr = 298.34	Dx = 1.543 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2911 reflections
a = 11.1646 (4) Å	θ = 2.4–26.4°
b = 8.8148 (2) Å	µ = 0.43 mm^−1
c = 13.0731 (4) Å	T = 293 K
β = 93.542 (2)°	Prism, colorless
V = 1284.11 (7) Å^3	0.5 × 0.4 × 0.4 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2413 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 26.4°, θmin = 2.4°
ϕ scans	h = 0→13
2739 measured reflections	k = 0→10
2562 independent reflections	l = −16→16

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0394P)^2 + 0.5975P] where P = (Fo^2 + 2Fc^2)/3
2562 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Geometry. All standard uncertainties (except dihedral angles between l.s. planes) are estimated using the full covariance matrix. The standard uncertainties in cell dimensions are are used in calculating the standard uncertainties of bond distances, angles and torsion angles. Angles between l.s. planes have standard uncertainties calculated from atomic positional standard uncertainties; the errors in cell dimensions are not used in this case.

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.25806 (4)	0.40727 (6)	0.44835 (4)	0.04078 (16)
S2	0.62052 (4)	0.45893 (5)	0.24580 (4)	0.04230 (16)
O1	0.36588 (13)	0.35967 (19)	0.50528 (12)	0.0578 (4)
O2	0.14641 (13)	0.33404 (18)	0.46719 (13)	0.0582 (4)
O3	0.61385 (15)	0.13746 (18)	0.26099 (17)	0.0698 (5)
O4	0.43483 (14)	0.11085 (16)	0.31285 (15)	0.0614 (4)
N1	0.41650 (13)	0.58423 (17)	0.26909 (12)	0.0381 (3)
N2	0.51753 (15)	0.18878 (18)	0.28407 (13)	0.0449 (4)
C1	0.24032 (16)	0.6046 (2)	0.46387 (14)	0.0389 (4)
C2	0.12568 (18)	0.6654 (2)	0.45680 (15)	0.0456 (4)
C3	0.1118 (2)	0.8210 (3)	0.46669 (17)	0.0581 (6)
C4	0.2102 (3)	0.9130 (3)	0.48087 (18)	0.0644 (6)
C5	0.3244 (2)	0.8512 (3)	0.48763 (18)	0.0636 (6)
C6	0.34097 (19)	0.6964 (3)	0.48004 (16)	0.0512 (5)
C7	0.27910 (15)	0.3814 (2)	0.31408 (15)	0.0393 (4)
C8	0.40000 (15)	0.4334 (2)	0.28634 (13)	0.0342 (4)
C9	0.52758 (16)	0.6140 (2)	0.24900 (15)	0.0383 (4)
C10	0.50176 (15)	0.3492 (2)	0.27680 (14)	0.0360 (4)
C11	0.5744 (2)	0.7693 (2)	0.23484 (19)	0.0538 (5)
H11A	0.6579	0.7649	0.2212	0.065*	0.50
H11B	0.5649	0.8276	0.2958	0.065*	0.50
H11C	0.5302	0.8163	0.1780	0.065*	0.50
H11D	0.6322	0.7964	0.2935	0.065*	0.50
H11E	0.5039	0.8344	0.2397	0.065*	0.50
H11F	0.6254	0.7742	0.1747	0.065*	0.50
H14	0.0564	0.6018	0.4449	0.055*
H18	0.0329	0.8648	0.4639	0.070*
H13	0.1995	1.0207	0.4865	0.077*
H19	0.3924	0.9175	0.4974	0.076*
H16	0.4206	0.6550	0.4857	0.061*
H12A	0.2186	0.4387	0.2757	0.047*
H12B	0.2697	0.2756	0.2982	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0297 (2)	0.0425 (3)	0.0509 (3)	0.00182 (17)	0.00777 (18)	0.00746 (19)
S2	0.0320 (2)	0.0356 (3)	0.0602 (3)	0.00028 (17)	0.00986 (19)	0.0010 (2)
O1	0.0442 (8)	0.0716 (10)	0.0569 (9)	0.0158 (7)	−0.0022 (6)	0.0143 (8)
O2	0.0424 (8)	0.0527 (9)	0.0820 (11)	−0.0071 (7)	0.0231 (7)	0.0079 (8)
O3	0.0548 (9)	0.0392 (8)	0.1177 (15)	0.0143 (7)	0.0237 (9)	−0.0041 (9)
O4	0.0551 (9)	0.0339 (7)	0.0959 (12)	−0.0077 (7)	0.0105 (8)	0.0059 (7)
N1	0.0357 (8)	0.0302 (7)	0.0489 (9)	0.0017 (6)	0.0055 (6)	0.0006 (6)
N2	0.0444 (9)	0.0306 (8)	0.0599 (10)	0.0010 (7)	0.0043 (7)	−0.0019 (7)
C1	0.0345 (9)	0.0449 (10)	0.0376 (9)	−0.0001 (7)	0.0050 (7)	0.0004 (7)
C2	0.0384 (10)	0.0514 (12)	0.0477 (11)	0.0048 (8)	0.0071 (8)	−0.0006 (9)
C3	0.0653 (14)	0.0553 (13)	0.0544 (13)	0.0169 (11)	0.0101 (10)	−0.0001 (10)
C4	0.0952 (19)	0.0470 (12)	0.0520 (13)	0.0033 (13)	0.0117 (12)	−0.0001 (10)
C5	0.0751 (16)	0.0596 (14)	0.0563 (13)	−0.0254 (12)	0.0049 (11)	−0.0061 (11)
C6	0.0406 (10)	0.0616 (13)	0.0512 (11)	−0.0094 (9)	0.0014 (8)	−0.0049 (10)
C7	0.0294 (8)	0.0360 (9)	0.0524 (11)	−0.0025 (7)	0.0033 (7)	−0.0024 (8)
C8	0.0319 (8)	0.0319 (9)	0.0389 (9)	−0.0010 (7)	0.0023 (7)	−0.0013 (7)
C9	0.0374 (9)	0.0314 (9)	0.0464 (10)	−0.0005 (7)	0.0041 (7)	0.0007 (7)
C10	0.0342 (9)	0.0293 (9)	0.0450 (10)	0.0005 (7)	0.0053 (7)	−0.0010 (7)
C11	0.0530 (12)	0.0327 (10)	0.0763 (15)	−0.0063 (9)	0.0094 (10)	0.0043 (9)

Geometric parameters (Å, º)

S1—O2	1.4384 (14)	C4—C5	1.384 (4)
S1—O1	1.4383 (15)	C4—H13	0.96
S1—C1	1.764 (2)	C5—C6	1.382 (3)
S1—C7	1.800 (2)	C5—H19	0.96
S2—C10	1.7103 (18)	C6—H16	0.96
S2—C9	1.7184 (18)	C7—C8	1.491 (2)
O3—N2	1.222 (2)	C7—H12A	0.96
O4—N2	1.228 (2)	C7—H12B	0.96
N1—C9	1.310 (2)	C8—C10	1.369 (2)
N1—C8	1.363 (2)	C9—C11	1.481 (3)
N2—C10	1.427 (2)	C11—H11A	0.96
C1—C2	1.385 (3)	C11—H11B	0.96
C1—C6	1.390 (3)	C11—H11C	0.96
C2—C3	1.388 (3)	C11—H11D	1.00
C2—H14	0.96	C11—H11E	0.98
C3—C4	1.369 (4)	C11—H11F	1.00
C3—H18	0.96
O2—S1—O1	119.14 (10)	C11—C9—S2	120.94 (14)
O2—S1—C1	108.55 (9)	C8—C10—N2	129.10 (16)
O1—S1—C1	108.94 (10)	C8—C10—S2	112.00 (13)
O2—S1—C7	106.07 (9)	N2—C10—S2	118.81 (13)
O1—S1—C7	108.19 (9)	C1—C2—H14	121.1
C1—S1—C7	105.05 (9)	C3—C2—H14	119.9
C10—S2—C9	88.06 (8)	C4—C3—H18	119.6
C9—N1—C8	111.60 (15)	C2—C3—H18	120.1
O3—N2—O4	123.94 (17)	C3—C4—H13	119.5
O3—N2—C10	117.22 (16)	C5—C4—H13	120.2
O4—N2—C10	118.84 (16)	C6—C5—H19	120.2
C2—C1—C6	121.3 (2)	C4—C5—H19	119.1
C2—C1—S1	118.93 (15)	C5—C6—H16	119.8
C6—C1—S1	119.73 (15)	C1—C6—H16	121.8
C1—C2—C3	119.0 (2)	C8—C7—H12A	109.2
C4—C3—C2	120.3 (2)	S1—C7—H12A	108.3
C3—C4—C5	120.3 (2)	C8—C7—H12B	109.5
C6—C5—C4	120.7 (2)	S1—C7—H12B	108.4
C5—C6—C1	118.4 (2)	C9—C11—H11A	109.9
C8—C7—S1	111.89 (13)	C9—C11—H11B	109.5
N1—C8—C10	113.11 (15)	C9—C11—H11C	109.1
N1—C8—C7	118.28 (15)	C9—C11—H11D	109.9
C10—C8—C7	128.60 (16)	C9—C11—H11E	104.0
N1—C9—C11	123.78 (17)	C9—C11—H11F	111.2
N1—C9—S2	115.21 (13)