2-Diazo-1-(1,1-dioxothio-morpholin-4-yl)ethanone.

In the mol-ecule of the title compound, C(6)H(9)N(3)O(3)S, at 105 K, the six-membered ring is predominantly found in the chair conformation, with 1.89 (14)% in the boat conformation. In the crystal structure, there are five inter-molecular C-H⋯O=C and C-H⋯O=S contacts less than 2.6 Å, as well as a weak C-H⋯N=N inter-action to the diazo group.

Related literature

For related structures found in the Cambridge Structural Database (Version 5.32 of November 2010; Allen, 2002 ▶), see: Fenlon et al. (2007 ▶); Haynes et al. (2006 ▶); Wang et al. (2006 ▶); Miller et al. (1991 ▶); Foces-Foces et al. (1988 ▶); Ganguly et al. (1980 ▶); Herdklotz & Sass (1969 ▶). For details of the synthesis, see: Kaupang (2010 ▶); Toma et al. (2007 ▶) and for the synthesis of related diazo­acetamides, see: Kaupang et al. (2010 ▶); Kaupang (2010 ▶); Ouihia et al. (1993 ▶). For quantum chemical calculations involving the acetamide analogue of the title compound, see: Fraenkel et al. (1992 ▶). For the Chemical Abstracts Service, see: American Chemical Society (2008 ▶). For hydrogen-bond graph-set notation, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C6H9N3O3S

M = 203.22

Monoclinic,

a = 5.2729 (3) Å

b = 20.1349 (11) Å

c = 7.8683 (4) Å

β = 95.171 (2)°

V = 831.97 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 105 K

0.80 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.849, T max = 0.929

14742 measured reflections

3951 independent reflections

3029 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.165

S = 1.11

3951 reflections

138 parameters

13 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.24 e Å−3

Δρmin = −0.71 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023774/si2361sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023774/si2361Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023774/si2361Isup3.cml

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

C6H9N3O3S	F(000) = 424
Mr = 203.22	Dx = 1.622 Mg m−3
Monoclinic, P21/n	Melting point = 438–449 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.2729 (3) Å	Cell parameters from 5309 reflections
b = 20.1349 (11) Å	θ = 2.8–36.6°
c = 7.8683 (4) Å	µ = 0.37 mm−1
β = 95.171 (2)°	T = 105 K
V = 831.97 (8) Å3	Needle, yellow
Z = 4	0.80 × 0.30 × 0.20 mm

Bruker APEXII CCD diffractometer	3951 independent reflections
Radiation source: fine-focus sealed tube	3029 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 8.3 pixels mm-1	θmax = 36.8°, θmin = 2.0°
Sets of exposures each taken over 0.5° ω rotation scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −30→32
Tmin = 0.849, Tmax = 0.929	l = −11→13
14742 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0728P)2 + 1.0103P] where P = (Fo2 + 2Fc2)/3
3951 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 1.24 e Å−3
13 restraints	Δρmin = −0.71 e Å−3

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 > 2σ(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	Occ. (<1)
S1	0.12602 (8)	0.17713 (2)	0.58307 (5)	0.01306 (11)	0.9811 (14)
O3	−0.1485 (2)	0.17127 (7)	0.56520 (19)	0.0176 (3)	0.9811 (14)
O2	0.2367 (3)	0.21336 (7)	0.73056 (18)	0.0194 (3)	0.9811 (14)
C5	0.2645 (3)	0.09728 (9)	0.5781 (2)	0.0152 (3)	0.9811 (14)
H51	0.4524	0.1012	0.5913	0.018*	0.9811 (14)
H52	0.2115	0.0703	0.6739	0.018*	0.9811 (14)
C6	0.2280 (3)	0.21174 (9)	0.3937 (2)	0.0156 (3)	0.9811 (14)
H61	0.1529	0.2565	0.3747	0.019*	0.9811 (14)
H62	0.4157	0.2163	0.4051	0.019*	0.9811 (14)
S11	0.385 (3)	0.1792 (3)	0.5843 (11)	0.013*	0.0189 (14)
O12	0.6562 (19)	0.1779 (9)	0.569 (4)	0.018*	0.0189 (14)
O13	0.302 (7)	0.2139 (3)	0.7308 (6)	0.0194 (3)	0.0189 (14)
C15	0.2645 (3)	0.09728 (9)	0.5781 (2)	0.0152 (3)	0.0189 (14)
H151	0.3969	0.0687	0.6379	0.018*	0.0189 (14)
H152	0.1168	0.0968	0.6474	0.018*	0.0189 (14)
C16	0.2280 (3)	0.21174 (9)	0.3937 (2)	0.0156 (3)	0.0189 (14)
H161	0.0734	0.2348	0.4255	0.019*	0.0189 (14)
H162	0.3408	0.2463	0.3519	0.019*	0.0189 (14)
O1	0.5857 (3)	0.02988 (7)	0.23496 (18)	0.0199 (3)
N1	0.2562 (3)	0.10078 (8)	0.26290 (19)	0.0153 (3)
C3	0.1799 (3)	0.06335 (9)	0.4088 (2)	0.0158 (3)
H31	0.2552	0.0183	0.4081	0.019*
H32	−0.0077	0.0585	0.3982	0.019*
C4	0.1452 (4)	0.16671 (9)	0.2410 (2)	0.0175 (3)
H41	−0.042 (3)	0.1625 (15)	0.232 (4)	0.021*
H42	0.197 (5)	0.1864 (13)	0.135 (3)	0.021*
C1	0.4582 (3)	0.07843 (9)	0.1828 (2)	0.0146 (3)
C2	0.5141 (4)	0.11299 (10)	0.0274 (2)	0.0173 (3)
H2	0.410 (5)	0.1428 (12)	−0.039 (3)	0.021*
N2	0.7103 (3)	0.08892 (9)	−0.0445 (2)	0.0200 (3)
N3	0.8809 (4)	0.06859 (12)	−0.1020 (2)	0.0294 (4)

	U11	U22	U33	U12	U13	U23
S1	0.01136 (17)	0.01274 (19)	0.01499 (19)	0.00030 (13)	0.00065 (12)	−0.00052 (13)
O3	0.0102 (5)	0.0198 (6)	0.0230 (6)	0.0005 (4)	0.0021 (4)	0.0000 (5)
O2	0.0209 (6)	0.0185 (6)	0.0182 (6)	−0.0011 (5)	−0.0011 (5)	−0.0042 (5)
C5	0.0151 (7)	0.0143 (7)	0.0163 (7)	0.0017 (5)	0.0013 (5)	0.0016 (5)
C6	0.0160 (7)	0.0132 (7)	0.0175 (7)	0.0001 (5)	0.0010 (5)	0.0017 (5)
O13	0.0209 (6)	0.0185 (6)	0.0182 (6)	−0.0011 (5)	−0.0011 (5)	−0.0042 (5)
C15	0.0151 (7)	0.0143 (7)	0.0163 (7)	0.0017 (5)	0.0013 (5)	0.0016 (5)
C16	0.0160 (7)	0.0132 (7)	0.0175 (7)	0.0001 (5)	0.0010 (5)	0.0017 (5)
O1	0.0195 (6)	0.0180 (6)	0.0224 (6)	0.0039 (5)	0.0026 (5)	0.0040 (5)
N1	0.0182 (6)	0.0130 (6)	0.0151 (6)	0.0021 (5)	0.0032 (5)	0.0019 (5)
C3	0.0177 (7)	0.0132 (7)	0.0168 (7)	−0.0010 (5)	0.0036 (5)	0.0008 (5)
C4	0.0207 (8)	0.0146 (8)	0.0169 (7)	0.0038 (6)	0.0005 (6)	0.0013 (5)
C1	0.0151 (7)	0.0144 (7)	0.0140 (7)	−0.0013 (5)	−0.0003 (5)	−0.0004 (5)
C2	0.0186 (7)	0.0190 (8)	0.0143 (7)	−0.0008 (6)	0.0013 (5)	0.0007 (6)
N2	0.0199 (7)	0.0243 (8)	0.0160 (7)	−0.0043 (6)	0.0022 (5)	0.0005 (5)
N3	0.0240 (8)	0.0410 (11)	0.0245 (9)	0.0015 (8)	0.0087 (7)	0.0003 (7)

S1—O3	1.4463 (13)	O1—C1	1.235 (2)
S1—O2	1.4482 (14)	N1—C1	1.362 (2)
S1—C5	1.7679 (18)	N1—C4	1.455 (2)
S1—C6	1.7718 (18)	N1—C3	1.460 (2)
C5—C3	1.528 (3)	C3—H31	0.9900
C5—H51	0.9900	C3—H32	0.9900
C5—H52	0.9900	C4—H41	0.984 (17)
C6—C4	1.537 (3)	C4—H42	0.983 (16)
C6—H61	0.9900	C1—C2	1.460 (2)
C6—H62	0.9900	C2—N2	1.316 (2)
S11—O12	1.446 (2)	C2—H2	0.940 (17)
S11—O13	1.448 (2)	N2—N3	1.120 (2)
O3—S1—O2	116.52 (9)	C4—N1—C3	115.30 (14)
O3—S1—C5	109.59 (8)	N1—C3—C5	112.05 (14)
O2—S1—C5	109.77 (9)	N1—C3—H31	109.2
O3—S1—C6	109.11 (9)	C5—C3—H31	109.2
O2—S1—C6	110.17 (9)	N1—C3—H32	109.2
C5—S1—C6	100.48 (8)	C5—C3—H32	109.2
C3—C5—S1	109.70 (12)	H31—C3—H32	107.9
C3—C5—H51	109.7	N1—C4—C6	111.28 (15)
S1—C5—H51	109.7	N1—C4—H41	108.6 (17)
C3—C5—H52	109.7	C6—C4—H41	108.7 (17)
S1—C5—H52	109.7	N1—C4—H42	109.1 (17)
H51—C5—H52	108.2	C6—C4—H42	110.1 (17)
C4—C6—S1	109.81 (12)	H41—C4—H42	109 (2)
C4—C6—H61	109.7	O1—C1—N1	122.16 (16)
S1—C6—H61	109.7	O1—C1—C2	120.72 (16)
C4—C6—H62	109.7	N1—C1—C2	117.09 (16)
S1—C6—H62	109.7	N2—C2—C1	114.24 (17)
H61—C6—H62	108.2	N2—C2—H2	116.1 (17)
O12—S11—O13	116.5 (3)	C1—C2—H2	128.1 (18)
C1—N1—C4	124.74 (15)	N3—N2—C2	178.3 (2)
C1—N1—C3	118.42 (15)
O3—S1—C5—C3	59.85 (14)	C3—N1—C4—C6	62.7 (2)
O2—S1—C5—C3	−170.98 (12)	S1—C6—C4—N1	−60.49 (17)
C6—S1—C5—C3	−54.93 (13)	C4—N1—C1—O1	161.34 (18)
O3—S1—C6—C4	−59.84 (14)	C3—N1—C1—O1	−3.9 (3)
O2—S1—C6—C4	171.06 (12)	C4—N1—C1—C2	−20.7 (3)
C5—S1—C6—C4	55.31 (13)	C3—N1—C1—C2	174.07 (15)
C1—N1—C3—C5	103.74 (18)	O1—C1—C2—N2	−1.7 (3)
C4—N1—C3—C5	−62.8 (2)	N1—C1—C2—N2	−179.68 (16)
S1—C5—C3—N1	60.09 (17)	C1—C2—N2—N3	−53 (8)
C1—N1—C4—C6	−102.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.94 (2)	2.42 (2)	3.326 (2)	163 (2)
C3—H32···O1ii	0.99	2.47	3.372 (2)	152
C5—H52···O1iii	0.99	2.36	3.022 (2)	123
C5—H51···O3iv	0.99	2.56	3.445 (2)	149
C5—H52···N3v	0.99	2.59	3.417 (3)	141
C6—H61···O2vi	0.99	2.45	3.168 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.94 (2)	2.42 (2)	3.326 (2)	163 (2)
C3—H32⋯O1ii	0.99	2.47	3.372 (2)	152
C5—H52⋯O1iii	0.99	2.36	3.022 (2)	123
C5—H51⋯O3iv	0.99	2.56	3.445 (2)	149
C5—H52⋯N3v	0.99	2.59	3.417 (3)	141
C6—H61⋯O2vi	0.99	2.45	3.168 (2)	129

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .