Dimethyl[(E)-(2-nitromethylidene-1,3-dithiolan-4-yl)methyl]amine.

In the title compound, C(7)H(12)N(2)O(2)S(2), the conformation of the dithia-cyclo-pentane ring is a half-chair, with a total puckering amplitude Q(T) = 0.473 (5) Å. Inter-molecular C-H⋯N and C-H⋯O inter-actions help to establish the packing.

Related literature

For the crystal structures of related compounds, see: Xu et al. (2005 ▶); Ortega-Jimenez et al. (2000 ▶). For the biological activities of heterocyclic compounds, see: Xu et al. (2006 ▶); Yu et al. (2009 ▶). For puckering amplitude, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C7H12N2O2S2

M = 220.31

Orthorhombic,

a = 5.927 (4) Å

b = 11.241 (8) Å

c = 14.90 (1) Å

V = 992.7 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.51 mm−1

T = 113 K

0.30 × 0.18 × 0.08 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.863, T max = 0.961

10308 measured reflections

2346 independent reflections

2099 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.090

S = 1.02

2346 reflections

120 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.39 e Å−3

Absolute structure: Flack (1983 ▶), 963 Friedel pairs

Flack parameter: −0.02 (10)

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812021307/hg5213sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021307/hg5213Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021307/hg5213Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H12N2O2S2	F(000) = 464
Mr = 220.31	Dx = 1.474 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3456 reflections
a = 5.927 (4) Å	θ = 1.8–27.8°
b = 11.241 (8) Å	µ = 0.51 mm−1
c = 14.90 (1) Å	T = 113 K
V = 992.7 (11) Å3	Prism, colorless
Z = 4	0.30 × 0.18 × 0.08 mm

Rigaku Saturn CCD area-detector diffractometer	2346 independent reflections
Radiation source: rotating anode	2099 reflections with I > 2σ(I)
Multilayer monochromator	Rint = 0.051
Detector resolution: 14.63 pixels mm-1	θmax = 27.8°, θmin = 2.3°
ω and φ scans	h = −6→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −14→14
Tmin = 0.863, Tmax = 0.961	l = −19→19
10308 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0465P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2346 reflections	Δρmax = 0.48 e Å−3
120 parameters	Δρmin = −0.39 e Å−3
0 restraints	Absolute structure: Flack (1983), 963 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (10)

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.

	x	y	z	Uiso*/Ueq
S1	0.16147 (11)	0.88829 (5)	0.02451 (4)	0.02114 (16)
S2	−0.05675 (11)	1.12418 (5)	0.02804 (4)	0.02176 (16)
O1	−0.4710 (3)	0.96345 (17)	−0.18337 (13)	0.0307 (5)
O2	−0.3988 (3)	1.10926 (16)	−0.09091 (12)	0.0276 (4)
N1	−0.3632 (4)	1.00756 (17)	−0.12006 (14)	0.0222 (5)
N2	0.4568 (4)	0.81812 (18)	0.18117 (14)	0.0196 (5)
C1	−0.1909 (5)	0.9375 (2)	−0.08113 (16)	0.0203 (5)
H1	−0.1734	0.8573	−0.0999	0.024*
C2	−0.0496 (4)	0.9819 (2)	−0.01767 (17)	0.0192 (5)
C3	0.1989 (5)	1.1078 (2)	0.09357 (18)	0.0256 (6)
H3A	0.3319	1.1288	0.0566	0.031*
H3B	0.1945	1.1617	0.1461	0.031*
C4	0.2158 (4)	0.9797 (2)	0.12456 (17)	0.0225 (6)
H4	0.0973	0.9636	0.1708	0.027*
C5	0.4449 (5)	0.9457 (2)	0.16155 (18)	0.0247 (6)
H5A	0.5630	0.9667	0.1173	0.030*
H5B	0.4743	0.9914	0.2172	0.030*
C6	0.3446 (5)	0.7885 (2)	0.26605 (17)	0.0255 (6)
H6A	0.3518	0.7023	0.2759	0.038*
H6B	0.1865	0.8137	0.2634	0.038*
H6C	0.4206	0.8295	0.3156	0.038*
C7	0.6931 (4)	0.7797 (3)	0.18472 (18)	0.0261 (6)
H7A	0.7689	0.8189	0.2352	0.039*
H7B	0.7688	0.8014	0.1286	0.039*
H7C	0.6995	0.6933	0.1928	0.039*

	U11	U22	U33	U12	U13	U23
S1	0.0270 (3)	0.0141 (3)	0.0223 (3)	0.0024 (3)	−0.0050 (3)	−0.0022 (3)
S2	0.0298 (4)	0.0134 (3)	0.0220 (3)	0.0023 (3)	−0.0032 (3)	−0.0015 (3)
O1	0.0375 (12)	0.0268 (10)	0.0279 (10)	−0.0037 (9)	−0.0164 (9)	−0.0017 (8)
O2	0.0313 (11)	0.0185 (9)	0.0330 (10)	0.0037 (8)	−0.0065 (8)	−0.0030 (8)
N1	0.0268 (12)	0.0167 (10)	0.0231 (11)	−0.0006 (9)	−0.0035 (10)	0.0016 (8)
N2	0.0235 (11)	0.0156 (10)	0.0198 (11)	0.0034 (9)	−0.0015 (9)	0.0023 (8)
C1	0.0270 (14)	0.0140 (11)	0.0198 (12)	0.0031 (11)	−0.0008 (11)	0.0006 (9)
C2	0.0219 (13)	0.0180 (11)	0.0177 (12)	−0.0001 (10)	0.0007 (11)	0.0028 (10)
C3	0.0344 (15)	0.0145 (11)	0.0279 (13)	−0.0005 (11)	−0.0100 (12)	−0.0005 (10)
C4	0.0263 (15)	0.0189 (12)	0.0221 (13)	−0.0007 (11)	−0.0016 (11)	−0.0007 (10)
C5	0.0296 (15)	0.0167 (12)	0.0277 (14)	−0.0022 (12)	−0.0055 (13)	−0.0007 (10)
C6	0.0291 (15)	0.0226 (13)	0.0248 (13)	0.0045 (12)	0.0021 (12)	0.0015 (11)
C7	0.0252 (15)	0.0266 (14)	0.0265 (14)	0.0027 (12)	0.0022 (12)	−0.0005 (11)

S1—C2	1.752 (2)	C3—H3A	0.9900
S1—C4	1.839 (3)	C3—H3B	0.9900
S2—C2	1.739 (3)	C4—C5	1.514 (4)
S2—C3	1.812 (3)	C4—H4	1.0000
O1—N1	1.243 (3)	C5—H5A	0.9900
O2—N1	1.241 (3)	C5—H5B	0.9900
N1—C1	1.414 (3)	C6—H6A	0.9800
N2—C5	1.466 (3)	C6—H6B	0.9800
N2—C7	1.466 (3)	C6—H6C	0.9800
N2—C6	1.467 (3)	C7—H7A	0.9800
C1—C2	1.358 (3)	C7—H7B	0.9800
C1—H1	0.9500	C7—H7C	0.9800
C3—C4	1.516 (4)
C2—S1—C4	94.61 (12)	C3—C4—S1	105.80 (18)
C2—S2—C3	95.60 (12)	C5—C4—H4	109.5
O2—N1—O1	123.1 (2)	C3—C4—H4	109.5
O2—N1—C1	119.5 (2)	S1—C4—H4	109.5
O1—N1—C1	117.4 (2)	N2—C5—C4	111.3 (2)
C5—N2—C7	110.0 (2)	N2—C5—H5A	109.4
C5—N2—C6	111.9 (2)	C4—C5—H5A	109.4
C7—N2—C6	109.6 (2)	N2—C5—H5B	109.4
C2—C1—N1	121.8 (2)	C4—C5—H5B	109.4
C2—C1—H1	119.1	H5A—C5—H5B	108.0
N1—C1—H1	119.1	N2—C6—H6A	109.5
C1—C2—S2	126.56 (19)	N2—C6—H6B	109.5
C1—C2—S1	118.00 (19)	H6A—C6—H6B	109.5
S2—C2—S1	115.43 (14)	N2—C6—H6C	109.5
C4—C3—S2	108.41 (18)	H6A—C6—H6C	109.5
C4—C3—H3A	110.0	H6B—C6—H6C	109.5
S2—C3—H3A	110.0	N2—C7—H7A	109.5
C4—C3—H3B	110.0	N2—C7—H7B	109.5
S2—C3—H3B	110.0	H7A—C7—H7B	109.5
H3A—C3—H3B	108.4	N2—C7—H7C	109.5
C5—C4—C3	114.2 (2)	H7A—C7—H7C	109.5
C5—C4—S1	108.15 (18)	H7B—C7—H7C	109.5
O2—N1—C1—C2	−5.7 (4)	S2—C3—C4—C5	166.65 (18)
O1—N1—C1—C2	173.5 (2)	S2—C3—C4—S1	47.8 (2)
N1—C1—C2—S2	1.8 (4)	C2—S1—C4—C5	−161.36 (17)
N1—C1—C2—S1	−178.79 (18)	C2—S1—C4—C3	−38.61 (19)
C3—S2—C2—C1	−174.4 (2)	C7—N2—C5—C4	159.4 (2)
C3—S2—C2—S1	6.22 (17)	C6—N2—C5—C4	−78.6 (3)
C4—S1—C2—C1	−162.7 (2)	C3—C4—C5—N2	−173.9 (2)
C4—S1—C2—S2	16.82 (16)	S1—C4—C5—N2	−56.4 (2)
C2—S2—C3—C4	−33.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N2i	0.95	2.44	3.354 (4)	161
C4—H4···O1ii	1.00	2.44	3.272 (4)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N2i	0.95	2.44	3.354 (4)	161
C4—H4⋯O1ii	1.00	2.44	3.272 (4)	140

Symmetry codes: (i) ; (ii) .