N-(3H-Thia­zol-2-yl­idene)­nitr­amine and N-methyl-N-(thia­zol-2-yl)­nitr­amine

The geometries of the thia­zole ring and the nitr­amino groups in N-(3H-thia­zol-2-yl­idene)­nitr­amine, C₃H₃N₃O₂S, (I), and N-­methyl-N-(thia­zol-2-yl)­nitr­amine, C₄H₅N₃O₂S, (II), are very similar. The nitr­amine group in (II) is planar and twisted along the C—N bond with respect to the thia­zole ring. In both structures, the asymmetric unit includes two practically equal mol­ecules. In (I), the mol­ecules are arranged in layers connected to each other by N—H...N and much weaker C—H...O hydrogen bonds. In the crystal structure of (II), the mol­ecules are arranged in layers bound to each other by both weak C—H...O hydrogen bonds and S...O dipolar interactions.

S1. Comment

Primary nitramines display acidic properties, e.g. the pK_a values of ring substituted N-phenylnitramines vary from 3.77 to 5.62, depending on the electronic character of the substituent (Daszkiewicz, Spaleniak & Kyzioł, 2002). N-(4-Pyridyl)nitramine is much less acidic (pK_a = 8.01), probably as a result of tautomerism; in the crystalline lattice it exists in the nitrimine form, i.e. as 1,4-dihydro-4-nitriminopyridine (Krygowski et al., 1996). IR spectroscopy indicates that the nitrimine form also prevails in solution (Kyzioł et al., 2002). The molecule of N-(thiazol-2-ylidene)nitramine, (I), also contains acidic (NHNO₂) and basic (—N═) centers and hence analogous tautomerism cannot be excluded. However, the acidity (pK_a = 4.00) is similar to that of typical primary nitramines.

Within the pyridine series, we have observed some differences in the geometry of the ring and the NNO₂ group between nitramine and isomeric nitrimine (Kyzioł et al., 2002). In the present paper, we establish the structure of N-(thiazol-2-ylidene)nitramine to be (Ib) (see scheme and Fig. 1) and compare this structure with that of N-methyl-N-(thiazol-2-yl)nitramine, (II) (Fig. 2), and its isomer 2,3-dihydro-3-methyl-2-nitriminothiazole, (III) (Kyzioł et al., 2000).

The geometries of the thiazole rings and the nitramine groups in (Ib) and (II) are very similar (Tables 1 and 3). The formally single C2—N3 bond in (Ib) is only 0.03 Å longer than that in (II), while the C2—N6 bond is 0.05 Å shorter. Surprisingly, the N–N bond lengths are nearly the same in the two compounds. The mean N3—C2—S1 angle is greater in nitramine (II) [115.9 (1)°] than in nitrimine (Ib) [110.6 (2)°]. Significant differences are also seen in the mean C2—N3—C4 angle, which is 109.3 (1)° in (II) and 114.9 (1)° in (Ib), The geometry of the ring is typical of thiazole derivatives (e.g. Caranoni & Reboul, 1982).

The shapes of the NNO₂ groups are also very similar; the mean N—O bonds in (Ib) and (II) are 1.243 (6) and 1.229 (2) Å, respectively. The results correspond well to the notation given on the scheme above.

The nitramine group in (II) is planar and twisted along the C2—N6 bond with respect to the thiazole ring; details of relevant torsion angles are given in Table 3. In other N-aryl-N-methylnitramines, the planes of the nitramine group and the thiazole ring are nearly perpendicular (Daszkiewicz, Zaleski et al., 2002). Such a conformation probably results from the crystal packing since the rotational energy barrier (ca 12 kJ mol⁻¹) along the aryl–N bond is rather low. Spectral and chemical properties of thiazolylnitramines are very similar to phenyl- and pyridylnitramines, hence the mesomeric interaction between the nitramine group and the thiazole ring may be excluded.

Hydrogen bonding plays an important role in the crystal packing of (Ib). In the IR spectrum (in a KBr pellet), the hydrogen bonding is observed as an intense and broad band in the 3100–2626 cm⁻¹ region, with several submaxima. The band corresponding to the N—H stretching vibrations appears at 3604 cm⁻¹, when the spectrum is registered in a diluted solution in deuterochloroform. Molecules of (Ib) are linked by N—H···N and weak C—H···O hydrogen bonds (Table 2), forming layers in the ac plane (Fig. 3). The shortest S···O separations are S1···O8'(x, 2 − y, 0.5 + z) of 3.219 (2) Å and S1'···O8 of 3.148 (2) Å. Molecules of (II) are linked by weak C—H···O hydrogen bonds (Table 4), forming layers in the ab plane (Fig. 4). Close intermolecular contacts are also found between S and O atoms [S1···O8' = 3.145 (2) Å and S1'···O8(1 + x, y, z) = 3.048 (2) Å], which are shorter than the sum of the van der Waals radii (3.25 Å; Pauling, 1960).

S2. Experimental

The preparation of (Ib) by nitration of 2-aminothiazole in 77% sulfuric acid was previously described previously by Kyzioł et al. (2000). Crystals were obtained by crystallization from nitromethane. Compound (II) was obtained according to the method of Angeli (Angeli & Valovi, 1912). 2-(N-Methylamino)thiazole (2.30 g, 0.02 mol) and sodium hydride (1.60 g, 0.04 mol of 60% NaH) in a boiling benzene (120 ml) was refluxed for 1 h under a dry nitrogen atmosphere. The mixture was cooled to room temperature and n-butyl nitrate (5.00 g, 0.04 mol) diluted with benzene (5 ml) was added. A brown solution was stirred for 1 h at room temperature, water (20 ml) and acetic acid (2 ml) were added and the layers separated. The benzene solution was extracted with sodium hydrogen sulfate (10% aqueous, 2 × 30 ml) and water, dried with anhydrous magnesium sulfate and evaporated in a vacuum. The residue was dissolved in n-hexane, stirred with charcoal, filtered and cooled in a dry-ice box. Compound (II) (1.75 g, 55%) was collected by filtration (m.p. 319–321 K). Low-temperature crystallization from n-hexane provided crystals suitable for the X-ray diffraction studies. MS (m/z): 145 (M⁺, 10), 113 (94), 86 (3), 69 (100), 59 (11), 58 (15), 42 (30), 30 (14). IR (KBr): 3130 (aromatic protons); 1537, 1272 (N-nitro group). ¹H NMR (DMSO-d₆): δ 7.70 (d, 1H) and 7.59 (d, ³J = 3.8 Hz, 1H, aromatic protons), 3.99 (s, 3H, N-methyl group); ¹³C NMR (DMSO-d₆): δ 157.8 (C–2), 138.7 (C–4), 118.2 (C–5), 37.3 (N-methyl group).

S3. Refinement

All H atoms were located from difference maps and subsequently treated as riding atoms, with C—H = 0.93–0.98 Å and N—H = 0.86 Å, and with U_iso(H) = 1.2U_eq(C or N), and 1.5U_eq(C) for the methyl H atoms.

Computing details

For both compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED; data reduction: CrysAlis RED (Oxford Diffraction, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. The molecular structure of (Ib). Displacement ellipsoids are drawn at the 50% probability level. Fig. 2. The molecular structure of (II). Displacement ellipsoids are drawn at the 50% probability level. Fig. 3. A packing diagrams of (Ib), showing the hydrogen-bonding scheme. Atoms marked with asterisk (*), hash (#), dollar sign ($) or ampersand (&) are at the symmetry positions (1 − x, 1 − y, 1 − z), (x, 1 − y, 1/2 + z),(-x, −y, −z) and (x, −y, 1/2 + z), respectively. Fig. 4. A packing diagrams of (II), showing the C—H···O hydrogen bonds and the short S···O separations. Atoms marked with an asterisk (*) are at the symmetry position (1 + x, y, z).

(I)

Crystal data

C3H3N3O2S	F(000) = 592
Mr = 145.14	Dx = 1.827 Mg m^−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 2459 reflections
a = 18.737 (3) Å	θ = 3.5–27.6°
b = 3.727 (1) Å	µ = 0.53 mm^−1
c = 16.617 (2) Å	T = 100 K
β = 114.57 (2)°	Irregular, white
V = 1055.3 (4) Å^3	0.3 × 0.3 × 0.2 mm
Z = 8

Data collection

Xcalibur diffractometer	1915 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
Graphite monochromator	θmax = 29.7°, θmin = 3.4°
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm^-1	h = −26→23
ω scans	k = −5→3
7430 measured reflections	l = −22→23
2740 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0449P)^2] where P = (Fo^2 + 2Fc^2)/3
2740 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −0.39 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	0.30727 (3)	0.99960 (13)	0.45518 (3)	0.01361 (13)
C2	0.39426 (11)	0.7904 (5)	0.47205 (12)	0.0126 (4)
N3	0.43519 (9)	0.7149 (4)	0.55744 (10)	0.0139 (3)
H3	0.4798	0.6075	0.5770	0.017*
C4	0.40037 (12)	0.8226 (5)	0.61216 (13)	0.0171 (4)
H4	0.4226	0.7880	0.6731	0.021*
C5	0.33115 (11)	0.9822 (5)	0.56756 (13)	0.0160 (4)
H5	0.2996	1.0729	0.5937	0.019*
N6	0.42570 (9)	0.6901 (4)	0.41530 (10)	0.0141 (3)
N7	0.38360 (9)	0.7706 (4)	0.32978 (11)	0.0166 (4)
O8	0.31882 (8)	0.9266 (4)	0.30423 (9)	0.0193 (3)
O9	0.41379 (9)	0.6832 (4)	0.27911 (9)	0.0241 (4)
S1'	0.18949 (3)	0.49066 (13)	0.15011 (3)	0.01294 (13)
C2'	0.10362 (10)	0.2892 (5)	0.07853 (12)	0.0114 (4)
N3'	0.06265 (9)	0.1717 (4)	0.12250 (10)	0.0124 (3)
H3'	0.0184	0.0631	0.0967	0.015*
C4'	0.09642 (11)	0.2372 (5)	0.21211 (13)	0.0151 (4)
H4'	0.0741	0.1696	0.2504	0.018*
C5'	0.16518 (11)	0.4094 (5)	0.23794 (13)	0.0155 (4)
H5'	0.1960	0.4769	0.2960	0.019*
N6'	0.07359 (9)	0.2316 (4)	−0.00929 (10)	0.0130 (3)
N7'	0.11444 (9)	0.3667 (4)	−0.05252 (11)	0.0147 (3)
O8'	0.17677 (8)	0.5354 (4)	−0.01257 (9)	0.0179 (3)
O9'	0.08580 (8)	0.3145 (4)	−0.13329 (9)	0.0224 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0107 (2)	0.0141 (2)	0.0170 (3)	0.00138 (19)	0.00683 (18)	0.0008 (2)
C2	0.0120 (9)	0.0111 (9)	0.0148 (10)	−0.0023 (7)	0.0058 (7)	−0.0004 (7)
N3	0.0096 (7)	0.0170 (8)	0.0166 (9)	0.0009 (6)	0.0069 (6)	0.0007 (7)
C4	0.0229 (10)	0.0171 (10)	0.0157 (10)	−0.0022 (8)	0.0122 (9)	0.0000 (8)
C5	0.0151 (9)	0.0171 (10)	0.0213 (10)	−0.0021 (8)	0.0130 (8)	−0.0015 (9)
N6	0.0127 (8)	0.0184 (9)	0.0117 (8)	0.0028 (7)	0.0055 (6)	0.0016 (7)
N7	0.0172 (8)	0.0177 (9)	0.0160 (9)	−0.0006 (7)	0.0078 (7)	0.0001 (7)
O8	0.0129 (7)	0.0251 (8)	0.0171 (7)	0.0054 (6)	0.0035 (6)	0.0030 (6)
O9	0.0272 (8)	0.0342 (9)	0.0155 (7)	0.0043 (7)	0.0135 (6)	−0.0008 (7)
S1'	0.0108 (2)	0.0142 (2)	0.0137 (2)	−0.00073 (19)	0.00488 (18)	−0.00009 (19)
C2'	0.0092 (8)	0.0118 (9)	0.0148 (9)	0.0020 (7)	0.0066 (7)	0.0001 (7)
N3'	0.0093 (7)	0.0148 (8)	0.0131 (8)	−0.0003 (6)	0.0046 (6)	0.0001 (7)
C4'	0.0155 (9)	0.0172 (10)	0.0139 (10)	0.0045 (8)	0.0075 (8)	0.0037 (8)
C5'	0.0179 (9)	0.0162 (10)	0.0105 (9)	0.0005 (8)	0.0041 (8)	−0.0009 (7)
N6'	0.0115 (7)	0.0174 (8)	0.0124 (8)	−0.0022 (6)	0.0073 (6)	0.0003 (7)
N7'	0.0150 (8)	0.0166 (8)	0.0150 (9)	0.0026 (7)	0.0087 (7)	0.0026 (7)
O8'	0.0138 (7)	0.0229 (8)	0.0194 (8)	−0.0044 (6)	0.0092 (6)	−0.0018 (6)
O9'	0.0256 (8)	0.0317 (9)	0.0118 (7)	−0.0020 (7)	0.0097 (6)	−0.0001 (6)

Geometric parameters (Å, º)

S1—C2	1.721 (2)	S1'—C2'	1.725 (2)
S1—C5	1.731 (2)	S1'—C5'	1.727 (2)
C2—N3	1.333 (2)	C2'—N3'	1.335 (2)
C2—N6	1.356 (2)	C2'—N6'	1.345 (2)
N3—C4	1.381 (2)	N3'—C4'	1.376 (2)
N3—H3	0.8600	N3'—H3'	0.8600
C4—C5	1.336 (3)	C4'—C5'	1.340 (3)
C4—H4	0.9300	C4'—H4'	0.9300
C5—H5	0.9300	C5'—H5'	0.9300
N6—N7	1.342 (2)	N6'—N7'	1.346 (2)
N7—O9	1.237 (2)	N7'—O9'	1.236 (2)
N7—O8	1.250 (2)	N7'—O8'	1.247 (2)
C2—S1—C5	90.28 (9)	C2'—S1'—C5'	90.47 (9)
N3—C2—N6	117.28 (17)	N3'—C2'—N6'	117.72 (16)
N3—C2—S1	110.84 (14)	N3'—C2'—S1'	110.44 (14)
N6—C2—S1	131.88 (15)	N6'—C2'—S1'	131.84 (14)
C2—N3—C4	114.80 (16)	C2'—N3'—C4'	115.08 (16)
C2—N3—H3	122.6	C2'—N3'—H3'	122.5
C4—N3—H3	122.6	C4'—N3'—H3'	122.5
C5—C4—N3	112.30 (18)	C5'—C4'—N3'	112.32 (17)
C5—C4—H4	123.8	C5'—C4'—H4'	123.8
N3—C4—H4	123.8	N3'—C4'—H4'	123.8
C4—C5—S1	111.77 (15)	C4'—C5'—S1'	111.69 (15)
C4—C5—H5	124.1	C4'—C5'—H5'	124.2
S1—C5—H5	124.1	S1'—C5'—H5'	124.2
N7—N6—C2	116.17 (15)	C2'—N6'—N7'	116.43 (15)
O9—N7—O8	123.05 (16)	O9'—N7'—O8'	123.03 (16)
O9—N7—N6	115.34 (16)	O9'—N7'—N6'	115.72 (16)
O8—N7—N6	121.61 (16)	O8'—N7'—N6'	121.24 (15)
C5—S1—C2—N3	0.89 (14)	C5'—S1'—C2'—N3'	−0.58 (15)
C5—S1—C2—N6	179.7 (2)	C5'—S1'—C2'—N6'	−179.78 (19)
N6—C2—N3—C4	−179.91 (16)	N6'—C2'—N3'—C4'	179.78 (16)
S1—C2—N3—C4	−0.9 (2)	S1'—C2'—N3'—C4'	0.4 (2)
C2—N3—C4—C5	0.3 (2)	C2'—N3'—C4'—C5'	0.0 (2)
N3—C4—C5—S1	0.4 (2)	N3'—C4'—C5'—S1'	−0.4 (2)
C2—S1—C5—C4	−0.73 (16)	C2'—S1'—C5'—C4'	0.59 (16)
N3—C2—N6—N7	−179.69 (16)	N3'—C2'—N6'—N7'	177.19 (15)
S1—C2—N6—N7	1.5 (3)	S1'—C2'—N6'—N7'	−3.7 (3)
C2—N6—N7—O9	178.72 (16)	C2'—N6'—N7'—O9'	−179.38 (16)
C2—N6—N7—O8	−0.6 (3)	C2'—N6'—N7'—O8'	0.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N6^i	0.86	2.05	2.880 (2)	163
N3′—H3′···N6′^ii	0.86	2.05	2.885 (2)	163
C4—H4···O9^iii	0.93	2.54	3.276 (2)	136
C4′—H4′···O9′^iv	0.93	2.59	3.360 (2)	141

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

(II)

Crystal data

C4H5N3O2S	F(000) = 656
Mr = 159.17	Dx = 1.658 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3361 reflections
a = 8.667 (2) Å	θ = 2.4–30.1°
b = 11.473 (2) Å	µ = 0.44 mm^−1
c = 12.919 (3) Å	T = 100 K
β = 96.80 (3)°	Irregular, white
V = 1275.6 (5) Å^3	0.25 × 0.2 × 0.2 mm
Z = 8

Data collection

Xcalibur diffractometer	2340 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.010
Graphite monochromator	θmax = 30.1°, θmin = 2.4°
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm^-1	h = −12→0
ω scans	k = 0→15
3561 measured reflections	l = −18→18
3361 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0393P)^2 + 0.7169P] where P = (Fo^2 + 2Fc^2)/3
3361 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.32 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.

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

	x	y	z	Uiso*/Ueq
S1	0.15707 (5)	0.21555 (4)	0.11778 (4)	0.01397 (11)
C2	0.09372 (19)	0.07272 (15)	0.12059 (13)	0.0119 (3)
N3	0.19874 (17)	−0.00679 (14)	0.11239 (12)	0.0147 (3)
C4	0.3392 (2)	0.04609 (17)	0.10351 (15)	0.0165 (4)
H4	0.4305	0.0024	0.0965	0.020*
C5	0.3392 (2)	0.16380 (17)	0.10540 (14)	0.0160 (4)
H5	0.4279	0.2112	0.1005	0.019*
N6	−0.05729 (17)	0.03816 (14)	0.13485 (12)	0.0137 (3)
N7	−0.17529 (17)	0.11562 (14)	0.12426 (12)	0.0162 (3)
O8	−0.14380 (16)	0.21882 (12)	0.11233 (13)	0.0245 (3)
O9	−0.30683 (15)	0.07760 (13)	0.12789 (11)	0.0211 (3)
C10	−0.0956 (2)	−0.08336 (16)	0.15409 (15)	0.0167 (4)
H10A	−0.1502	−0.0881	0.2162	0.025*
H10B	0.0001	−0.1294	0.1651	0.025*
H10C	−0.1626	−0.1141	0.0938	0.025*
S1'	0.66132 (5)	0.43921 (4)	0.11936 (3)	0.01350 (11)
C2'	0.6036 (2)	0.58282 (16)	0.12696 (13)	0.0123 (3)
N3'	0.71028 (18)	0.66079 (14)	0.11917 (12)	0.0161 (3)
C4'	0.8481 (2)	0.60599 (17)	0.10618 (14)	0.0171 (4)
H4'	0.9403	0.6485	0.0992	0.020*
C5'	0.8444 (2)	0.48844 (17)	0.10386 (14)	0.0161 (4)
H5'	0.9306	0.4399	0.0949	0.019*
N6'	0.45361 (17)	0.62050 (14)	0.14153 (12)	0.0143 (3)
N7'	0.33631 (18)	0.54327 (15)	0.14488 (12)	0.0159 (3)
O8'	0.36874 (16)	0.43870 (12)	0.14500 (11)	0.0212 (3)
O9'	0.20578 (15)	0.58321 (14)	0.14807 (11)	0.0217 (3)
C10'	0.4130 (2)	0.74420 (18)	0.14208 (17)	0.0230 (4)
H10D	0.3473	0.7637	0.0774	0.034*
H10E	0.5081	0.7912	0.1474	0.034*
H10F	0.3565	0.7606	0.2018	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0123 (2)	0.0106 (2)	0.0194 (2)	−0.00114 (16)	0.00320 (15)	−0.00044 (16)
C2	0.0097 (7)	0.0122 (9)	0.0137 (8)	−0.0007 (6)	0.0011 (6)	0.0009 (6)
N3	0.0115 (7)	0.0139 (8)	0.0191 (7)	0.0004 (6)	0.0027 (5)	0.0008 (6)
C4	0.0100 (8)	0.0189 (9)	0.0206 (9)	0.0005 (7)	0.0022 (6)	0.0005 (7)
C5	0.0112 (7)	0.0193 (10)	0.0178 (8)	−0.0021 (7)	0.0024 (6)	−0.0001 (7)
N6	0.0093 (6)	0.0117 (7)	0.0204 (7)	−0.0002 (6)	0.0030 (5)	0.0013 (6)
N7	0.0104 (6)	0.0178 (8)	0.0206 (8)	0.0020 (6)	0.0023 (6)	−0.0012 (6)
O8	0.0172 (7)	0.0131 (7)	0.0436 (9)	0.0028 (5)	0.0054 (6)	0.0022 (6)
O9	0.0092 (6)	0.0261 (8)	0.0282 (7)	−0.0008 (5)	0.0029 (5)	−0.0010 (6)
C10	0.0161 (8)	0.0126 (9)	0.0219 (9)	−0.0036 (7)	0.0040 (7)	0.0012 (7)
S1'	0.0122 (2)	0.0110 (2)	0.0175 (2)	0.00123 (16)	0.00251 (15)	0.00032 (16)
C2'	0.0117 (7)	0.0114 (8)	0.0139 (8)	0.0017 (6)	0.0012 (6)	0.0003 (6)
N3'	0.0138 (7)	0.0142 (8)	0.0202 (7)	−0.0001 (6)	0.0017 (6)	0.0003 (6)
C4'	0.0114 (8)	0.0199 (10)	0.0200 (8)	−0.0013 (7)	0.0023 (6)	0.0015 (7)
C5'	0.0102 (8)	0.0202 (10)	0.0184 (8)	0.0020 (7)	0.0030 (6)	0.0015 (7)
N6'	0.0108 (6)	0.0127 (7)	0.0198 (7)	0.0016 (6)	0.0031 (5)	−0.0007 (6)
N7'	0.0120 (7)	0.0200 (8)	0.0157 (7)	0.0000 (6)	0.0024 (5)	−0.0003 (6)
O8'	0.0169 (7)	0.0164 (7)	0.0310 (8)	−0.0017 (5)	0.0057 (6)	0.0006 (6)
O9'	0.0108 (6)	0.0307 (8)	0.0240 (7)	0.0037 (6)	0.0037 (5)	0.0007 (6)
C10'	0.0197 (9)	0.0131 (9)	0.0360 (11)	0.0063 (8)	0.0029 (8)	−0.0029 (8)

Geometric parameters (Å, º)

S1—C2	1.7300 (18)	S1'—C2'	1.7280 (19)
S1—C5	1.7118 (19)	S1'—C5'	1.7182 (19)
C2—N3	1.302 (2)	C2'—N3'	1.299 (2)
C2—N6	1.400 (2)	C2'—N6'	1.404 (2)
N3—C4	1.377 (2)	N3'—C4'	1.377 (2)
C4—C5	1.351 (3)	C4'—C5'	1.349 (3)
C4—H4	0.9500	C4'—H4'	0.9500
C5—H5	0.9500	C5'—H5'	0.9500
N6—N7	1.350 (2)	N6'—N7'	1.353 (2)
N6—C10	1.461 (2)	N6'—C10'	1.462 (2)
N7—O9	1.227 (2)	N7'—O9'	1.226 (2)
N7—O8	1.229 (2)	N7'—O8'	1.232 (2)
C10—H10A	0.9800	C10'—H10D	0.9800
C10—H10B	0.9800	C10'—H10E	0.9800
C10—H10C	0.9800	C10'—H10F	0.9800
C5—S1—C2	88.39 (9)	C5'—S1'—C2'	88.31 (9)
N3—C2—N6	119.05 (16)	N3'—C2'—N6'	118.50 (16)
N3—C2—S1	115.81 (13)	N3'—C2'—S1'	116.05 (13)
N6—C2—S1	125.09 (14)	N6'—C2'—S1'	125.45 (14)
C2—N3—C4	109.36 (16)	C2'—N3'—C4'	109.28 (16)
C5—C4—N3	115.94 (18)	C5'—C4'—N3'	116.13 (17)
C5—C4—H4	122.0	C5'—C4'—H4'	121.9
N3—C4—H4	122.0	N3'—C4'—H4'	121.9
C4—C5—S1	110.50 (15)	C4'—C5'—S1'	110.22 (14)
C4—C5—H5	124.8	C4'—C5'—H5'	124.9
S1—C5—H5	124.8	S1'—C5'—H5'	124.9
N7—N6—C2	120.60 (15)	N7'—N6'—C2'	120.92 (15)
N7—N6—C10	117.43 (15)	N7'—N6'—C10'	116.95 (15)
C2—N6—C10	121.83 (15)	C2'—N6'—C10'	121.79 (16)
O9—N7—O8	124.65 (16)	O9'—N7'—O8'	125.12 (17)
O9—N7—N6	117.29 (16)	O9'—N7'—N6'	117.14 (16)
O8—N7—N6	118.05 (15)	O8'—N7'—N6'	117.74 (15)
N6—C10—H10A	109.5	N6'—C10'—H10D	109.5
N6—C10—H10B	109.5	N6'—C10'—H10E	109.5
H10A—C10—H10B	109.5	H10D—C10'—H10E	109.5
N6—C10—H10C	109.5	N6'—C10'—H10F	109.5
H10A—C10—H10C	109.5	H10D—C10'—H10F	109.5
H10B—C10—H10C	109.5	H10E—C10'—H10F	109.5
C5—S1—C2—N3	−0.37 (15)	C5'—S1'—C2'—N3'	−0.25 (14)
C5—S1—C2—N6	177.02 (16)	C5'—S1'—C2'—N6'	−179.67 (16)
N6—C2—N3—C4	−177.39 (15)	N6'—C2'—N3'—C4'	179.52 (15)
S1—C2—N3—C4	0.2 (2)	S1'—C2'—N3'—C4'	0.05 (19)
C2—N3—C4—C5	0.2 (2)	C2'—N3'—C4'—C5'	0.2 (2)
N3—C4—C5—S1	−0.5 (2)	N3'—C4'—C5'—S1'	−0.4 (2)
C2—S1—C5—C4	0.46 (15)	C2'—S1'—C5'—C4'	0.36 (14)
N3—C2—N6—N7	−167.56 (16)	N3'—C2'—N6'—N7'	176.65 (16)
S1—C2—N6—N7	15.1 (2)	S1'—C2'—N6'—N7'	−3.9 (2)
N3—C2—N6—C10	8.0 (2)	N3'—C2'—N6'—C10'	3.6 (2)
S1—C2—N6—C10	−169.35 (13)	S1'—C2'—N6'—C10'	−177.03 (14)
C2—N6—N7—O9	173.20 (16)	C2'—N6'—N7'—O9'	−173.39 (15)
C10—N6—N7—O9	−2.5 (2)	C10'—N6'—N7'—O9'	0.0 (2)
C2—N6—N7—O8	−7.2 (2)	C2'—N6'—N7'—O8'	6.9 (2)
C10—N6—N7—O8	177.07 (16)	C10'—N6'—N7'—O8'	−179.64 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O9^i	0.95	2.42	3.068 (2)	125
C4′—H4′···O9′^i	0.95	2.43	3.094 (2)	127

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