Methylthioureas and their morpholine and dioxane adducts; hydrogen-bonding patterns

We have redetermined the known structures of (i) methylthiourea (MTU) and (ii) 1,1-dimethylthiourea (1,1-DMTU), and investigated the structure of 1,3-dimethylthiourea (1,3-DMTU), which was however severely disordered. We report the structures of crystalline adducts of (iii) MTU with morpholine (1:1), (iv) 1,1-DMTU with 1,4-dioxane (2:1) and (v) 1,3-DMTU with 1,4-dioxane (2:1). Finally, (vi) we determined the structure of tetramethylthiourea (TetMTU). (i) In both independent molecules of MTU, the methyl group is trans to the C=S group across the C—N bond. The two molecules are connected to form an R₂²(8) dimer by mutual N—H...S=C interactions. The packing involves six N—H...S=C interactions and is three-dimensional. (ii) The packing of the MTU–morpholine adduct is a layer structure, within which both molecules form linear aggregates parallel to the b axis. (iii) The packing of 1,1-DMTU involves N—H...S=C hydrogen bonds forming a corrugated layer structure. (iv) In the 2:1 adduct between 1,1-DMTU and 1,4-dioxane, the DMTU molecule occupies a general position whereas the dioxane molecule lies across an inversion centre. The crystal packing involves chains of alternating 1,1-DMTU R₂²(8) dimers and dioxanes, both across inversion centres. (v) In the 2:1 adduct between 1,3-DMTU and dioxane, the 1,3-DMTU molecule occupies a general position, while the dioxane molecule lies across an inversion centre. One methyl group of the DMTU is trans and one cis to the sulfur across the corresponding C—N bond. The molecules form chains of alternating 1,3-DMTU R₂²(8) dimers and dioxanes, both across inversion centres. Crystals of the 2:1 adduct between 1,3-DMTU and morpholine were also obtained, and were isotypic with the dioxane adduct. The morpholine molecule is disordered across the inversion centre. (vi) The molecule of TetMTU displays crystallographic twofold symmetry. Significant distortions reflect the steric pressure between methyl groups trans to sulfur. The packing of TetMTU involves only a weak hydrogen bond, C—H_methyl...S, which connects the molecules to form layers.

Computing details

Data collection: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) for birke, fichte, buche, kirsche, laerche; CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) for judo. Cell refinement: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) for birke, fichte, buche, kirsche, laerche; CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) for judo. Data reduction: CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) for birke, fichte, buche, kirsche, laerche; CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) for judo. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Bruker XP; software used to prepare material for publication: SHELXL97.

Figures

(birke)

Crystal data

C2H6N2S	Z = 4
Mr = 90.15	F(000) = 192
Triclinic, P1	Dx = 1.353 Mg m^−3
a = 7.6615 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6945 (6) Å	Cell parameters from 8424 reflections
c = 8.0283 (6) Å	θ = 2.7–30.8°
α = 78.182 (7)°	µ = 0.54 mm^−1
β = 73.785 (7)°	T = 100 K
γ = 81.448 (7)°	Needle, colourless
V = 442.71 (6) Å^3	0.30 × 0.08 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer	2543 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2283 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 16.1419 pixels mm^-1	θmax = 30.0°, θmin = 2.7°
ω–scan	h = −10→10
Absorption correction: multi-scan CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11)	k = −10→10
Tmin = 0.888, Tmax = 1.000	l = −11→10
23416 measured 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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.059	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0254P)^2 + 0.1207P] where P = (Fo^2 + 2Fc^2)/3
2543 reflections	(Δ/σ)max = 0.001
117 parameters	Δρmax = 0.31 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. NH H atoms were refined freely. The methyl groups were refined as idealized rigid groups allowed to rotate but not tip.

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

	x	y	z	Uiso*/Ueq
S1	0.80694 (3)	0.72454 (3)	0.06315 (3)	0.01543 (7)
N1	0.69504 (13)	0.65131 (12)	0.41019 (12)	0.01731 (18)
H01	0.637 (2)	0.746 (2)	0.3992 (19)	0.026 (4)*
N3	0.87845 (14)	0.42681 (12)	0.27962 (13)	0.01890 (19)
H02	0.850 (2)	0.351 (2)	0.374 (2)	0.025 (4)*
H03	0.945 (2)	0.393 (2)	0.188 (2)	0.024 (4)*
C2	0.79128 (13)	0.59066 (13)	0.26493 (13)	0.01379 (18)
C11	0.68790 (17)	0.55940 (15)	0.58900 (14)	0.0230 (2)
H11A	0.6102	0.4614	0.6184	0.034*
H11B	0.6372	0.6434	0.6711	0.034*
H11C	0.8114	0.5115	0.5980	0.034*
S1'	0.30721 (3)	0.94926 (3)	0.42276 (3)	0.01560 (7)
N1'	0.35908 (12)	0.84136 (12)	0.11870 (11)	0.01543 (17)
H01'	0.467 (2)	0.8374 (19)	0.1169 (19)	0.024 (4)*
N3'	0.05947 (12)	0.89571 (13)	0.26743 (12)	0.01723 (18)
H02'	0.021 (2)	0.866 (2)	0.184 (2)	0.028 (4)*
H03'	−0.019 (2)	0.9311 (19)	0.353 (2)	0.024 (4)*
C2'	0.23673 (13)	0.89313 (12)	0.25712 (13)	0.01321 (18)
C11'	0.31622 (15)	0.78088 (16)	−0.02406 (14)	0.0204 (2)
H11D	0.2594	0.6688	0.0211	0.031*
H11E	0.4288	0.7617	−0.1159	0.031*
H11F	0.2316	0.8714	−0.0737	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01311 (12)	0.01644 (12)	0.01520 (12)	0.00144 (9)	−0.00239 (9)	−0.00308 (9)
N1	0.0182 (4)	0.0138 (4)	0.0168 (4)	0.0005 (3)	0.0007 (3)	−0.0041 (3)
N3	0.0217 (5)	0.0168 (4)	0.0143 (4)	0.0040 (3)	−0.0009 (4)	−0.0035 (3)
C2	0.0099 (4)	0.0153 (4)	0.0169 (4)	−0.0027 (3)	−0.0022 (3)	−0.0048 (4)
C11	0.0294 (6)	0.0185 (5)	0.0157 (5)	−0.0013 (4)	0.0028 (4)	−0.0033 (4)
S1'	0.01314 (13)	0.01735 (12)	0.01736 (13)	−0.00040 (9)	−0.00304 (9)	−0.00732 (9)
N1'	0.0110 (4)	0.0187 (4)	0.0163 (4)	−0.0005 (3)	−0.0018 (3)	−0.0055 (3)
N3'	0.0111 (4)	0.0240 (5)	0.0172 (4)	−0.0010 (3)	−0.0011 (3)	−0.0088 (4)
C2'	0.0127 (4)	0.0107 (4)	0.0150 (4)	−0.0011 (3)	−0.0021 (3)	−0.0014 (3)
C11'	0.0176 (5)	0.0266 (5)	0.0180 (5)	−0.0009 (4)	−0.0017 (4)	−0.0111 (4)

Geometric parameters (Å, º)

S1—C2	1.7160 (10)	N3—H03	0.833 (16)
N1—C2	1.3273 (13)	C11—H11A	0.9800
N1—C11	1.4546 (14)	C11—H11B	0.9800
N3—C2	1.3350 (13)	C11—H11C	0.9800
S1'—C2'	1.7182 (10)	N1'—H01'	0.819 (16)
N1'—C2'	1.3270 (13)	N3'—H02'	0.878 (16)
N1'—C11'	1.4533 (13)	N3'—H03'	0.838 (16)
N3'—C2'	1.3348 (13)	C11'—H11D	0.9800
N1—H01	0.795 (16)	C11'—H11E	0.9800
N3—H02	0.853 (15)	C11'—H11F	0.9800
C2—N1—C11	125.21 (9)	H11A—C11—H11B	109.5
N1—C2—N3	118.87 (9)	N1—C11—H11C	109.5
N1—C2—S1	119.97 (8)	H11A—C11—H11C	109.5
N3—C2—S1	121.14 (8)	H11B—C11—H11C	109.5
C2'—N1'—C11'	125.04 (9)	C2'—N1'—H01'	117.3 (10)
N1'—C2'—N3'	118.97 (9)	C11'—N1'—H01'	117.6 (10)
N1'—C2'—S1'	120.05 (8)	C2'—N3'—H02'	122.0 (10)
N3'—C2'—S1'	120.95 (8)	C2'—N3'—H03'	119.9 (10)
C2—N1—H01	117.7 (11)	H02'—N3'—H03'	118.0 (14)
C11—N1—H01	117.0 (11)	N1'—C11'—H11D	109.5
C2—N3—H02	120.9 (10)	N1'—C11'—H11E	109.5
C2—N3—H03	117.8 (10)	H11D—C11'—H11E	109.5
H02—N3—H03	120.0 (14)	N1'—C11'—H11F	109.5
N1—C11—H11A	109.5	H11D—C11'—H11F	109.5
N1—C11—H11B	109.5	H11E—C11'—H11F	109.5
C11—N1—C2—N3	5.57 (16)	C11'—N1'—C2'—N3'	−1.86 (15)
C11—N1—C2—S1	−172.71 (8)	C11'—N1'—C2'—S1'	176.23 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···S1′	0.795 (16)	2.748 (16)	3.4636 (10)	150.7 (14)
N3—H02···S1′^i	0.853 (15)	2.766 (15)	3.5496 (11)	153.6 (13)
N3—H03···S1^ii	0.833 (16)	2.571 (16)	3.3930 (10)	169.6 (13)
N1′—H01′···S1	0.819 (16)	2.564 (16)	3.3426 (10)	159.1 (13)
N3′—H02′···S1^iii	0.878 (16)	2.588 (16)	3.4033 (10)	154.9 (13)
N3′—H03′···S1′^iv	0.838 (16)	2.612 (16)	3.4377 (10)	168.7 (13)

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

(fichte)

Crystal data

C3H8N2S	Dx = 1.324 Mg m^−3
Mr = 104.17	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 13412 reflections
a = 6.15884 (15) Å	θ = 2.2–30.9°
b = 11.5953 (3) Å	µ = 0.47 mm^−1
c = 14.6390 (4) Å	T = 100 K
V = 1045.42 (4) Å^3	Tablet, colourless
Z = 8	0.20 × 0.20 × 0.12 mm
F(000) = 448

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer	1620 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1433 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 16.1419 pixels mm^-1	θmax = 30.9°, θmin = 2.8°
ω–scan	h = −8→8
Absorption correction: multi-scan CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11)	k = −16→16
Tmin = 0.977, Tmax = 1.000	l = −20→20
47980 measured 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.063	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0271P)^2 + 0.4173P] where P = (Fo^2 + 2Fc^2)/3
1620 reflections	(Δ/σ)max = 0.004
65 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.21 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. NH H atoms were refined freely. The methyl groups were refined as idealized rigid groups allowed to rotate but not tip.

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

	x	y	z	Uiso*/Ueq
S1	0.86257 (4)	0.342915 (19)	0.560327 (16)	0.01637 (8)
N1	0.50612 (13)	0.42782 (7)	0.64388 (5)	0.01555 (16)
N3	0.73219 (16)	0.55819 (7)	0.57368 (6)	0.01929 (18)
H02	0.843 (2)	0.5724 (12)	0.5403 (10)	0.026 (4)*
H01	0.648 (2)	0.6158 (15)	0.5852 (11)	0.033 (4)*
C2	0.68672 (15)	0.44830 (7)	0.59527 (6)	0.01367 (17)
C11	0.43718 (17)	0.31185 (8)	0.66995 (7)	0.01888 (19)
H11A	0.5475	0.2559	0.6509	0.028*
H11B	0.2990	0.2937	0.6400	0.028*
H11C	0.4188	0.3081	0.7364	0.028*
C12	0.35777 (17)	0.52175 (9)	0.66800 (7)	0.0209 (2)
H12A	0.4311	0.5753	0.7096	0.031*
H12B	0.2288	0.4899	0.6980	0.031*
H12C	0.3142	0.5629	0.6125	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01796 (13)	0.01046 (12)	0.02067 (13)	0.00102 (8)	0.00495 (8)	0.00125 (8)
N1	0.0166 (4)	0.0137 (3)	0.0164 (4)	0.0008 (3)	0.0026 (3)	0.0003 (3)
N3	0.0221 (4)	0.0104 (4)	0.0254 (4)	0.0012 (3)	0.0067 (4)	0.0015 (3)
C2	0.0168 (4)	0.0119 (4)	0.0123 (4)	0.0001 (3)	−0.0012 (3)	0.0001 (3)
C11	0.0190 (5)	0.0172 (4)	0.0204 (5)	−0.0036 (4)	0.0027 (4)	0.0021 (3)
C12	0.0207 (5)	0.0209 (5)	0.0211 (5)	0.0060 (4)	0.0042 (4)	−0.0004 (4)

Geometric parameters (Å, º)

S1—C2	1.7111 (9)	C11—H11A	0.9800
N1—C2	1.3416 (12)	C11—H11B	0.9800
N1—C11	1.4608 (12)	C11—H11C	0.9800
N1—C12	1.4649 (12)	C12—H12A	0.9800
N3—C2	1.3423 (12)	C12—H12B	0.9800
N3—H02	0.854 (15)	C12—H12C	0.9800
N3—H01	0.861 (17)
C2—N1—C11	122.85 (8)	H11A—C11—H11B	109.5
C2—N1—C12	120.89 (8)	N1—C11—H11C	109.5
C11—N1—C12	116.11 (8)	H11A—C11—H11C	109.5
N1—C2—N3	117.77 (8)	H11B—C11—H11C	109.5
N1—C2—S1	123.84 (7)	N1—C12—H12A	109.5
N3—C2—S1	118.39 (7)	N1—C12—H12B	109.5
C2—N3—H02	119.0 (10)	H12A—C12—H12B	109.5
C2—N3—H01	124.4 (10)	N1—C12—H12C	109.5
H02—N3—H01	116.2 (13)	H12A—C12—H12C	109.5
N1—C11—H11A	109.5	H12B—C12—H12C	109.5
N1—C11—H11B	109.5
C11—N1—C2—N3	178.75 (9)	C11—N1—C2—S1	−1.84 (13)
C12—N1—C2—N3	3.34 (14)	C12—N1—C2—S1	−177.25 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H02···S1^i	0.854 (15)	2.535 (15)	3.3752 (9)	167.9 (13)
N3—H01···S1^ii	0.861 (17)	2.660 (17)	3.3584 (9)	139.1 (13)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+3/2, y+1/2, z.

(buche)

Crystal data

C6H15N3OS	F(000) = 384
Mr = 177.27	Dx = 1.274 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.56953 (19) Å	Cell parameters from 8511 reflections
b = 8.7346 (3) Å	θ = 2.3–30.8°
c = 16.2322 (5) Å	µ = 0.30 mm^−1
β = 96.964 (3)°	T = 100 K
V = 924.57 (5) Å^3	Block, colourless
Z = 4	0.60 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer	2766 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2481 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 16.1419 pixels mm^-1	θmax = 30.8°, θmin = 2.5°
ω–scan	h = −9→9
Absorption correction: multi-scan CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11)	k = −12→12
Tmin = 0.930, Tmax = 1.000	l = −22→23
24602 measured 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0279P)^2 + 0.2877P] where P = (Fo^2 + 2Fc^2)/3
2766 reflections	(Δ/σ)max = 0.001
117 parameters	Δρmax = 0.42 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. The NH hydrogen were refined freely. The methyl groups were refined as idealized rigid groups allowed to rotate but not tip. Other H atoms were included using a riding model starting from calculated positions.

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

	x	y	z	Uiso*/Ueq
S1	0.59279 (3)	0.25150 (2)	0.516867 (12)	0.01403 (6)
N1	0.26108 (10)	0.11300 (8)	0.44283 (4)	0.01374 (13)
H01	0.3227 (18)	0.0341 (14)	0.4585 (7)	0.022 (3)*
C2	0.35593 (12)	0.24655 (8)	0.45909 (5)	0.01128 (14)
N3	0.26259 (11)	0.37463 (8)	0.43036 (4)	0.01434 (13)
H02	0.147 (2)	0.3738 (15)	0.3978 (8)	0.030 (3)*
H03	0.3197 (18)	0.4598 (14)	0.4437 (7)	0.023 (3)*
C11	0.05684 (12)	0.09654 (10)	0.39797 (5)	0.01780 (16)
H11A	−0.0416	0.1542	0.4266	0.027*
H11B	0.0183	−0.0119	0.3956	0.027*
H11C	0.0561	0.1362	0.3415	0.027*
O1	−0.05655 (10)	0.75767 (7)	0.29741 (4)	0.01797 (13)
C3	0.08424 (13)	0.66044 (10)	0.26173 (5)	0.01771 (16)
H3A	0.2034	0.6386	0.3035	0.021*
H3B	0.1350	0.7133	0.2143	0.021*
C4	−0.01776 (14)	0.51139 (10)	0.23232 (5)	0.01901 (17)
H4A	−0.1326	0.5321	0.1884	0.023*
H4B	0.0823	0.4445	0.2088	0.023*
N4	−0.09532 (11)	0.43452 (8)	0.30303 (5)	0.01755 (15)
H04	−0.162 (2)	0.3584 (16)	0.2865 (8)	0.032 (3)*
C5	−0.23971 (13)	0.53543 (10)	0.33980 (5)	0.01836 (17)
H5A	−0.2881	0.4847	0.3884	0.022*
H5B	−0.3602	0.5566	0.2986	0.022*
C6	−0.13237 (13)	0.68363 (10)	0.36638 (5)	0.01742 (16)
H6A	−0.2294	0.7526	0.3903	0.021*
H6B	−0.0168	0.6623	0.4099	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01197 (10)	0.01029 (10)	0.01869 (11)	0.00015 (6)	−0.00278 (7)	0.00048 (6)
N1	0.0134 (3)	0.0088 (3)	0.0180 (3)	0.0003 (2)	−0.0021 (2)	0.0004 (2)
C2	0.0121 (3)	0.0111 (3)	0.0107 (3)	0.0005 (2)	0.0019 (3)	−0.0006 (2)
N3	0.0145 (3)	0.0093 (3)	0.0179 (3)	0.0000 (2)	−0.0034 (2)	0.0003 (2)
C11	0.0142 (3)	0.0133 (4)	0.0245 (4)	−0.0019 (3)	−0.0034 (3)	−0.0007 (3)
O1	0.0239 (3)	0.0129 (3)	0.0180 (3)	0.0028 (2)	0.0061 (2)	0.0027 (2)
C3	0.0189 (4)	0.0182 (4)	0.0169 (4)	0.0009 (3)	0.0057 (3)	0.0016 (3)
C4	0.0225 (4)	0.0187 (4)	0.0153 (4)	0.0030 (3)	0.0003 (3)	−0.0023 (3)
N4	0.0191 (3)	0.0128 (3)	0.0195 (3)	−0.0024 (3)	−0.0029 (3)	−0.0003 (3)
C5	0.0149 (4)	0.0215 (4)	0.0183 (4)	−0.0017 (3)	0.0007 (3)	0.0034 (3)
C6	0.0200 (4)	0.0185 (4)	0.0143 (3)	0.0015 (3)	0.0041 (3)	0.0004 (3)

Geometric parameters (Å, º)

S1—C2	1.7172 (8)	C11—H11A	0.9800
N1—C2	1.3337 (10)	C11—H11B	0.9800
N1—C11	1.4541 (10)	C11—H11C	0.9800
C2—N3	1.3326 (10)	C3—H3A	0.9900
O1—C3	1.4290 (10)	C3—H3B	0.9900
O1—C6	1.4335 (10)	C4—H4A	0.9900
C3—C4	1.5147 (12)	C4—H4B	0.9900
C4—N4	1.4729 (11)	N4—H04	0.822 (14)
N4—C5	1.4732 (11)	C5—H5A	0.9900
C5—C6	1.5117 (12)	C5—H5B	0.9900
N1—H01	0.824 (12)	C6—H6A	0.9900
N3—H02	0.872 (13)	C6—H6B	0.9900
N3—H03	0.850 (13)
C2—N1—C11	124.48 (7)	C4—C3—H3A	109.5
N3—C2—N1	118.74 (7)	O1—C3—H3B	109.5
N3—C2—S1	121.20 (6)	C4—C3—H3B	109.5
N1—C2—S1	120.05 (6)	H3A—C3—H3B	108.1
C3—O1—C6	110.59 (6)	N4—C4—H4A	109.9
O1—C3—C4	110.81 (7)	C3—C4—H4A	109.9
N4—C4—C3	109.13 (7)	N4—C4—H4B	109.9
C4—N4—C5	110.09 (7)	C3—C4—H4B	109.9
N4—C5—C6	109.09 (7)	H4A—C4—H4B	108.3
O1—C6—C5	110.95 (7)	C4—N4—H04	109.5 (9)
C2—N1—H01	118.1 (8)	C5—N4—H04	105.9 (9)
C11—N1—H01	117.4 (8)	N4—C5—H5A	109.9
C2—N3—H02	122.4 (9)	C6—C5—H5A	109.9
C2—N3—H03	118.4 (8)	N4—C5—H5B	109.9
H02—N3—H03	119.2 (12)	C6—C5—H5B	109.9
N1—C11—H11A	109.5	H5A—C5—H5B	108.3
N1—C11—H11B	109.5	O1—C6—H6A	109.4
H11A—C11—H11B	109.5	C5—C6—H6A	109.4
N1—C11—H11C	109.5	O1—C6—H6B	109.4
H11A—C11—H11C	109.5	C5—C6—H6B	109.4
H11B—C11—H11C	109.5	H6A—C6—H6B	108.0
O1—C3—H3A	109.5
C11—N1—C2—N3	−2.40 (12)	C3—C4—N4—C5	57.82 (9)
C11—N1—C2—S1	177.00 (6)	C4—N4—C5—C6	−57.74 (9)
C6—O1—C3—C4	59.15 (9)	C3—O1—C6—C5	−59.18 (9)
O1—C3—C4—N4	−58.36 (9)	N4—C5—C6—O1	58.19 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···S1^i	0.824 (12)	2.576 (13)	3.3665 (7)	161.2 (11)
N3—H02···N4	0.872 (13)	2.142 (13)	2.9826 (10)	162.0 (12)
N3—H03···S1^ii	0.850 (13)	2.647 (13)	3.4790 (7)	166.5 (10)
N4—H04···O1^iii	0.822 (14)	2.333 (14)	3.0611 (10)	147.9 (12)

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

(kirsche)

Crystal data

C5H12N2OS	F(000) = 320
Mr = 148.23	Dx = 1.295 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.4979 (2) Å	Cell parameters from 7968 reflections
b = 7.0116 (3) Å	θ = 2.4–30.8°
c = 16.7097 (6) Å	µ = 0.35 mm^−1
β = 92.982 (4)°	T = 100 K
V = 760.27 (5) Å^3	Tablet, colourless
Z = 4	0.40 × 0.34 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer	2295 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2020 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 16.1419 pixels mm^-1	θmax = 30.8°, θmin = 2.4°
ω–scan	h = −9→9
Absorption correction: multi-scan CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11)	k = −9→9
Tmin = 0.899, Tmax = 1.000	l = −23→24
26635 measured 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0335P)^2 + 0.3101P] where P = (Fo^2 + 2Fc^2)/3
2295 reflections	(Δ/σ)max = 0.001
92 parameters	Δρmax = 0.37 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. The NH hydrogen were refined freely. The methyl groups were refined as idealized rigid groups allowed to rotate but not tip. Other H atoms were included using a riding model starting from calculated positions.

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

	x	y	z	Uiso*/Ueq
S1	0.59561 (4)	0.36220 (4)	0.114934 (15)	0.01612 (8)
N3	0.28298 (16)	0.59360 (15)	0.07887 (6)	0.0190 (2)
H02	0.334 (3)	0.600 (2)	0.0319 (10)	0.029 (4)*
H01	0.184 (3)	0.665 (2)	0.0864 (9)	0.026 (4)*
N1	0.29207 (13)	0.47557 (13)	0.20694 (5)	0.01396 (17)
C2	0.37683 (15)	0.48453 (14)	0.13565 (6)	0.01304 (19)
C11	0.38771 (18)	0.36980 (17)	0.27453 (7)	0.0199 (2)
H11A	0.3071	0.2546	0.2840	0.030*
H11B	0.3917	0.4501	0.3226	0.030*
H11C	0.5284	0.3339	0.2623	0.030*
C12	0.10138 (16)	0.57891 (16)	0.22121 (7)	0.0168 (2)
H12A	0.1249	0.7162	0.2158	0.025*
H12B	0.0589	0.5512	0.2754	0.025*
H12C	−0.0072	0.5384	0.1820	0.025*
O1	−0.01188 (12)	0.91701 (11)	0.07707 (5)	0.01708 (16)
C4	0.09944 (17)	1.09107 (16)	0.06551 (6)	0.0178 (2)
H4A	0.2166	1.0993	0.1057	0.021*
H4B	0.0076	1.2013	0.0736	0.021*
C3	−0.17944 (16)	0.90051 (16)	0.01794 (6)	0.0172 (2)
H3A	−0.2788	1.0055	0.0248	0.021*
H3B	−0.2523	0.7782	0.0252	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01565 (13)	0.01862 (14)	0.01421 (13)	0.00477 (9)	0.00191 (9)	−0.00031 (9)
N3	0.0207 (5)	0.0236 (5)	0.0130 (4)	0.0094 (4)	0.0032 (3)	0.0026 (4)
N1	0.0154 (4)	0.0142 (4)	0.0125 (4)	0.0022 (3)	0.0018 (3)	0.0006 (3)
C2	0.0140 (4)	0.0117 (4)	0.0134 (4)	−0.0003 (3)	0.0004 (3)	−0.0020 (3)
C11	0.0230 (5)	0.0219 (5)	0.0152 (5)	0.0063 (4)	0.0034 (4)	0.0051 (4)
C12	0.0146 (5)	0.0195 (5)	0.0165 (5)	0.0022 (4)	0.0034 (4)	−0.0005 (4)
O1	0.0185 (4)	0.0174 (4)	0.0153 (4)	0.0001 (3)	0.0002 (3)	0.0018 (3)
C4	0.0191 (5)	0.0186 (5)	0.0157 (5)	−0.0016 (4)	0.0005 (4)	−0.0026 (4)
C3	0.0153 (5)	0.0185 (5)	0.0179 (5)	−0.0007 (4)	0.0017 (4)	−0.0006 (4)

Geometric parameters (Å, º)

S1—C2	1.7111 (10)	C11—H11A	0.9800
N3—C2	1.3405 (14)	C11—H11B	0.9800
N1—C2	1.3396 (13)	C11—H11C	0.9800
N1—C11	1.4624 (14)	C12—H12A	0.9800
N1—C12	1.4656 (13)	C12—H12B	0.9800
O1—C3	1.4364 (13)	C12—H12C	0.9800
O1—C4	1.4369 (13)	C4—H4A	0.9900
C4—C3^i	1.5143 (15)	C4—H4B	0.9900
C3—C4^i	1.5143 (15)	C3—H3A	0.9900
N3—H02	0.868 (17)	C3—H3B	0.9900
N3—H01	0.832 (17)
C2—N1—C11	122.18 (9)	H11B—C11—H11C	109.5
C2—N1—C12	120.77 (9)	N1—C12—H12A	109.5
C11—N1—C12	117.00 (8)	N1—C12—H12B	109.5
N1—C2—N3	117.60 (9)	H12A—C12—H12B	109.5
N1—C2—S1	122.74 (8)	N1—C12—H12C	109.5
N3—C2—S1	119.66 (8)	H12A—C12—H12C	109.5
C3—O1—C4	110.17 (8)	H12B—C12—H12C	109.5
O1—C4—C3^i	110.87 (9)	O1—C4—H4A	109.5
O1—C3—C4^i	110.24 (9)	C3^i—C4—H4A	109.5
C2—N3—H02	119.3 (11)	O1—C4—H4B	109.5
C2—N3—H01	124.4 (11)	C3^i—C4—H4B	109.5
H02—N3—H01	116.1 (15)	H4A—C4—H4B	108.1
N1—C11—H11A	109.5	O1—C3—H3A	109.6
N1—C11—H11B	109.5	C4^i—C3—H3A	109.6
H11A—C11—H11B	109.5	O1—C3—H3B	109.6
N1—C11—H11C	109.5	C4^i—C3—H3B	109.6
H11A—C11—H11C	109.5	H3A—C3—H3B	108.1
C11—N1—C2—N3	−176.46 (10)	C12—N1—C2—S1	−178.35 (8)
C12—N1—C2—N3	1.16 (15)	C3—O1—C4—C3^i	−57.69 (12)
C11—N1—C2—S1	4.04 (15)	C4—O1—C3—C4^i	57.32 (12)

Symmetry code: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H02···S1^ii	0.868 (17)	2.533 (17)	3.3870 (10)	167.9 (14)
N3—H01···O1	0.832 (17)	2.177 (17)	2.9678 (13)	158.9 (15)

Symmetry code: (ii) −x+1, −y+1, −z.

(laerche)

Crystal data

C5H12N2OS	Z = 2
Mr = 148.23	F(000) = 160
Triclinic, P1	Dx = 1.275 Mg m^−3
a = 6.8470 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.0982 (4) Å	Cell parameters from 9890 reflections
c = 8.6412 (3) Å	θ = 2.6–30.8°
α = 106.676 (5)°	µ = 0.35 mm^−1
β = 105.448 (5)°	T = 100 K
γ = 90.679 (4)°	Irregular, colourless
V = 386.00 (3) Å^3	0.40 × 0.40 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer	2261 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2152 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 16.1419 pixels mm^-1	θmax = 30.8°, θmin = 2.6°
ω–scan	h = −9→9
Absorption correction: multi-scan CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11)	k = −10→10
Tmin = 0.963, Tmax = 1.000	l = −12→12
19849 measured 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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.060	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0286P)^2 + 0.1049P] where P = (Fo^2 + 2Fc^2)/3
2261 reflections	(Δ/σ)max = 0.001
92 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.19 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. The NH hydrogen were refined freely. The methyl groups were refined as idealized rigid groups allowed to rotate but not tip. Other H atoms were included using a riding model starting from calculated positions.

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

	x	y	z	Uiso*/Ueq
S1	0.79400 (3)	0.65322 (3)	0.83621 (2)	0.01647 (7)
N1	0.73593 (10)	0.32910 (10)	0.91781 (9)	0.01514 (13)
H01	0.858 (2)	0.3589 (18)	0.9756 (15)	0.023 (3)*
C11	0.62755 (12)	0.16044 (12)	0.93232 (11)	0.01757 (15)
H11A	0.5127	0.2041	0.9767	0.026*
H11B	0.7201	0.1010	1.0089	0.026*
H11C	0.5769	0.0625	0.8211	0.026*
C2	0.65055 (11)	0.45281 (11)	0.83380 (9)	0.01311 (14)
N3	0.45272 (10)	0.41150 (10)	0.74971 (9)	0.01643 (14)
H03	0.3923 (18)	0.3048 (19)	0.7456 (15)	0.022 (3)*
C31	0.33183 (13)	0.53097 (13)	0.65536 (11)	0.02079 (17)
H31A	0.3998	0.6652	0.6934	0.031*
H31B	0.1968	0.5359	0.6741	0.031*
H31C	0.3177	0.4722	0.5351	0.031*
O1	0.19088 (9)	0.03915 (10)	0.62293 (8)	0.02009 (13)
C3	0.17228 (13)	−0.05756 (15)	0.44879 (11)	0.02394 (18)
H3A	0.1566	−0.2025	0.4267	0.029*
H3B	0.2976	−0.0235	0.4221	0.029*
C4	0.00908 (13)	−0.00422 (13)	0.66256 (11)	0.01956 (16)
H4A	0.0218	0.0667	0.7821	0.023*
H4B	−0.0109	−0.1477	0.6463	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01465 (10)	0.01487 (10)	0.01981 (11)	−0.00181 (7)	0.00210 (7)	0.00777 (7)
N1	0.0116 (3)	0.0145 (3)	0.0192 (3)	−0.0004 (2)	0.0019 (2)	0.0071 (2)
C11	0.0169 (3)	0.0148 (3)	0.0221 (4)	−0.0006 (3)	0.0046 (3)	0.0082 (3)
C2	0.0134 (3)	0.0126 (3)	0.0127 (3)	0.0012 (2)	0.0044 (3)	0.0022 (3)
N3	0.0129 (3)	0.0150 (3)	0.0199 (3)	−0.0007 (2)	0.0009 (2)	0.0064 (3)
C31	0.0165 (4)	0.0218 (4)	0.0213 (4)	0.0024 (3)	−0.0015 (3)	0.0085 (3)
O1	0.0137 (3)	0.0267 (3)	0.0164 (3)	−0.0035 (2)	0.0013 (2)	0.0042 (2)
C3	0.0165 (4)	0.0363 (5)	0.0183 (4)	0.0047 (3)	0.0060 (3)	0.0059 (3)
C4	0.0182 (4)	0.0252 (4)	0.0160 (4)	−0.0010 (3)	0.0051 (3)	0.0073 (3)

Geometric parameters (Å, º)

S1—C2	1.7110 (8)	C11—H11B	0.9800
N1—C2	1.3386 (10)	C11—H11C	0.9800
N1—C11	1.4541 (10)	N3—H03	0.845 (13)
C2—N3	1.3389 (10)	C31—H31A	0.9800
N3—C31	1.4571 (11)	C31—H31B	0.9800
O1—C4	1.4283 (10)	C31—H31C	0.9800
O1—C3	1.4335 (11)	C3—H3A	0.9900
C3—C4^i	1.5095 (12)	C3—H3B	0.9900
C4—C3^i	1.5096 (12)	C4—H4A	0.9900
N1—H01	0.840 (13)	C4—H4B	0.9900
C11—H11A	0.9800
C2—N1—C11	124.91 (7)	C31—N3—H03	116.0 (8)
N1—C2—N3	117.26 (7)	N3—C31—H31A	109.5
N1—C2—S1	119.96 (6)	N3—C31—H31B	109.5
N3—C2—S1	122.79 (6)	H31A—C31—H31B	109.5
C2—N3—C31	125.38 (7)	N3—C31—H31C	109.5
C4—O1—C3	110.26 (6)	H31A—C31—H31C	109.5
O1—C3—C4^i	110.70 (7)	H31B—C31—H31C	109.5
O1—C4—C3^i	110.34 (7)	O1—C3—H3A	109.5
C2—N1—H01	117.3 (8)	C4^i—C3—H3A	109.5
C11—N1—H01	117.4 (8)	O1—C3—H3B	109.5
N1—C11—H11A	109.5	C4^i—C3—H3B	109.5
N1—C11—H11B	109.5	H3A—C3—H3B	108.1
H11A—C11—H11B	109.5	O1—C4—H4A	109.6
N1—C11—H11C	109.5	C3^i—C4—H4A	109.6
H11A—C11—H11C	109.5	O1—C4—H4B	109.6
H11B—C11—H11C	109.5	C3^i—C4—H4B	109.6
C2—N3—H03	118.5 (8)	H4A—C4—H4B	108.1
C11—N1—C2—N3	−3.70 (11)	S1—C2—N3—C31	−2.20 (11)
C11—N1—C2—S1	176.59 (6)	C4—O1—C3—C4^i	57.62 (10)
N1—C2—N3—C31	178.10 (8)	C3—O1—C4—C3^i	−57.41 (10)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···S1^ii	0.840 (13)	2.520 (13)	3.3295 (7)	162.2 (11)
N3—H03···O1	0.845 (13)	2.143 (13)	2.9290 (9)	154.4 (11)

Symmetry code: (ii) −x+2, −y+1, −z+2.

(judo)

Crystal data

C5H12N2S	F(000) = 288
Mr = 132.23	Dx = 1.228 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.4621 (2) Å	Cell parameters from 4399 reflections
b = 12.0353 (4) Å	θ = 3.4–30.8°
c = 10.9309 (4) Å	µ = 0.36 mm^−1
β = 95.641 (4)°	T = 100 K
V = 715.10 (4) Å^3	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer	988 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.022
Graphite monochromator	θmax = 30.8°, θmin = 3.4°
Detector resolution: 16.1419 pixels mm^-1	h = −7→7
ω–scan	k = −16→17
9123 measured reflections	l = −15→15
1072 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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.059	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0263P)^2 + 0.3639P] where P = (Fo^2 + 2Fc^2)/3
1072 reflections	(Δ/σ)max = 0.001
40 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.15 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. The methyl groups were refined as idealized rigid groups allowed to rotate but not tip.

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

	x	y	z	Uiso*/Ueq
S1	0.5000	0.60583 (2)	0.2500	0.02080 (10)
N1	0.38291 (13)	0.40519 (6)	0.33192 (6)	0.01719 (15)
C2	0.5000	0.46519 (9)	0.2500	0.0146 (2)
C11	0.19738 (16)	0.45517 (8)	0.40165 (8)	0.02223 (18)
H11A	0.2745	0.4799	0.4818	0.033*
H11B	0.0696	0.4002	0.4138	0.033*
H11C	0.1232	0.5190	0.3563	0.033*
C12	0.48412 (16)	0.30059 (7)	0.38405 (7)	0.02043 (17)
H12A	0.6417	0.2852	0.3517	0.031*
H12B	0.3688	0.2399	0.3615	0.031*
H12C	0.5094	0.3069	0.4738	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.02953 (17)	0.01594 (14)	0.01703 (14)	0.000	0.00277 (11)	0.000
N1	0.0189 (3)	0.0189 (3)	0.0145 (3)	0.0009 (2)	0.0060 (2)	0.0016 (2)
C2	0.0146 (4)	0.0180 (5)	0.0112 (4)	0.000	0.0004 (3)	0.000
C11	0.0194 (4)	0.0313 (4)	0.0171 (4)	0.0018 (3)	0.0073 (3)	−0.0012 (3)
C12	0.0263 (4)	0.0192 (4)	0.0159 (3)	−0.0009 (3)	0.0025 (3)	0.0031 (3)

Geometric parameters (Å, º)

S1—C2	1.6925 (11)	C11—H11B	0.9800
N1—C2	1.3583 (9)	C11—H11C	0.9800
N1—C11	1.4566 (10)	C12—H12A	0.9800
N1—C12	1.4674 (10)	C12—H12B	0.9800
C2—N1^i	1.3583 (9)	C12—H12C	0.9800
C11—H11A	0.9800
C2—N1—C11	121.49 (7)	H11A—C11—H11C	109.5
C2—N1—C12	121.89 (7)	H11B—C11—H11C	109.5
C11—N1—C12	113.95 (7)	N1—C12—H12A	109.5
N1^i—C2—N1	115.76 (10)	N1—C12—H12B	109.5
N1^i—C2—S1	122.12 (5)	H12A—C12—H12B	109.5
N1—C11—H11A	109.5	N1—C12—H12C	109.5
N1—C11—H11B	109.5	H12A—C12—H12C	109.5
H11A—C11—H11B	109.5	H12B—C12—H12C	109.5
N1—C11—H11C	109.5	N1—C2—S1	122.12 (5)
C11—N1—C2—N1^i	−163.00 (8)	C11—N1—C2—S1	17.00 (8)
C12—N1—C2—N1^i	36.64 (6)	C12—N1—C2—S1	−143.36 (6)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···S1^ii	0.98	2.77	3.7246 (9)	165

Symmetry code: (ii) x−1/2, y−1/2, z.