Ethyl 2-[(carbamothioyl-amino)-imino]-propano-ate.

The title compound, C(6)H(11)N(3)O(2)S, consists of a roughly planar mol-ecule (r.m.s deviation from planarity = 0.077 Å for the non-H atoms) and has the S atom in an anti position to the imine N atom. This N atom is the acceptor of a strongly bent inter-nal N-H⋯N hydrogen bond donated by the amino group. In the crystal, mol-ecules are arranged in undulating layers parallel to (010). The mol-ecules are linked via inter-molecular amino-carboxyl N-H⋯O hydrogen bonds, forming chains parallel to [001]. The chains are cross-linked by N(carbazone)-H⋯S and C-H⋯S inter-actions, forming infinite sheets.

Related literature

For the synthesis of thio­semicarbazones, see: Gupta & Narayana (1997 ▶); Li et al. (1998 ▶); Tarasconi et al. (2000 ▶); Holla et al. (2003 ▶); Shailendra et al. (2003 ▶). For the synthesis, crystal structures and applications of thio­semicarbazones, see: West et al. (1993 ▶); Casas et al. (2000 ▶); Beraldo (2004 ▶); Tenório et al. (2005 ▶). For graph-set notation, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C6H11N3O2S

M = 189.24

Monoclinic,

a = 16.682 (3) Å

b = 7.2558 (15) Å

c = 17.317 (4) Å

β = 116.63 (3)°

V = 1873.8 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.31 mm−1

T = 297 K

0.56 × 0.27 × 0.12 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

15270 measured reflections

2133 independent reflections

1785 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.092

S = 1.08

2133 reflections

123 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.26 e Å−3

Data collection: COLLECT (Hooft, 1999 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026237/qk2014sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026237/qk2014Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026237/qk2014Isup3.cml

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

C6H11N3O2S	F(000) = 800
Mr = 189.24	Dx = 1.342 Mg m−3
Monoclinic, C2/c	Melting point: 418 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 16.682 (3) Å	Cell parameters from 106 reflections
b = 7.2558 (15) Å	θ = 4.7–22.6°
c = 17.317 (4) Å	µ = 0.31 mm−1
β = 116.63 (3)°	T = 297 K
V = 1873.8 (7) Å3	Prism, colourless
Z = 8	0.56 × 0.27 × 0.12 mm

Bruker–Nonius KappaCCD diffractometer	1785 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
horizonally mounted graphite crystal	θmax = 27.5°, θmin = 5.3°
Detector resolution: 9 pixels mm-1	h = −21→21
ω and φ scans	k = −9→9
15270 measured reflections	l = −22→22
2133 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0423P)2 + 1.1077P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2133 reflections	Δρmax = 0.21 e Å−3
123 parameters	Δρmin = −0.26 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 > 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	0.07816 (2)	0.66899 (7)	0.18273 (2)	0.05007 (15)
O1	0.36286 (7)	0.42826 (16)	0.55879 (6)	0.0453 (3)
O2	0.29362 (8)	0.4511 (2)	0.64308 (7)	0.0599 (4)
N3	0.21829 (8)	0.52146 (17)	0.42323 (7)	0.0363 (3)
N2	0.14791 (8)	0.57872 (18)	0.34827 (7)	0.0394 (3)
N1	0.23628 (9)	0.5179 (2)	0.28107 (9)	0.0541 (4)
C2	0.21056 (9)	0.5244 (2)	0.49384 (9)	0.0365 (3)
C1	0.15936 (9)	0.5823 (2)	0.27447 (9)	0.0368 (3)
C4	0.29221 (9)	0.4639 (2)	0.57299 (9)	0.0378 (3)
C3	0.13145 (10)	0.5866 (3)	0.50629 (11)	0.0507 (4)
H3A	0.1298	0.7189	0.5069	0.076*
H3B	0.1365	0.5398	0.5601	0.076*
H3C	0.0773	0.5410	0.4598	0.076*
C6	0.51684 (12)	0.3513 (3)	0.60556 (14)	0.0644 (5)
H6A	0.4977	0.2588	0.5613	0.097*
H6B	0.5713	0.3122	0.6537	0.097*
H6C	0.5272	0.4650	0.5831	0.097*
C5	0.44536 (10)	0.3796 (3)	0.63469 (11)	0.0503 (4)
H5A	0.4368	0.2677	0.6607	0.060*
H5B	0.4626	0.4777	0.6772	0.060*
H1N	0.2740 (14)	0.476 (3)	0.3288 (14)	0.061 (6)*
H3N	0.0969 (12)	0.612 (2)	0.3430 (11)	0.045 (4)*
H2N	0.2477 (13)	0.525 (3)	0.2361 (14)	0.060 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.0402 (2)	0.0741 (3)	0.0365 (2)	0.00740 (18)	0.01775 (16)	0.01065 (17)
O1	0.0387 (5)	0.0663 (7)	0.0337 (5)	0.0055 (5)	0.0186 (4)	0.0026 (5)
O2	0.0558 (7)	0.0988 (10)	0.0322 (5)	0.0012 (6)	0.0260 (5)	−0.0006 (6)
N3	0.0358 (6)	0.0444 (6)	0.0318 (5)	−0.0029 (5)	0.0179 (5)	−0.0016 (5)
N2	0.0344 (6)	0.0552 (8)	0.0339 (6)	0.0028 (5)	0.0200 (5)	0.0027 (5)
N1	0.0421 (7)	0.0910 (12)	0.0369 (7)	0.0153 (7)	0.0246 (6)	0.0118 (7)
C2	0.0385 (7)	0.0425 (7)	0.0343 (6)	−0.0052 (6)	0.0213 (6)	−0.0043 (6)
C1	0.0352 (6)	0.0456 (8)	0.0333 (6)	−0.0042 (6)	0.0185 (5)	−0.0004 (6)
C4	0.0415 (7)	0.0440 (8)	0.0334 (7)	−0.0053 (6)	0.0216 (6)	−0.0056 (6)
C3	0.0431 (8)	0.0733 (11)	0.0454 (8)	0.0025 (8)	0.0284 (7)	−0.0012 (8)
C6	0.0447 (9)	0.0665 (12)	0.0798 (13)	0.0050 (8)	0.0259 (9)	−0.0007 (10)
C5	0.0430 (8)	0.0574 (10)	0.0432 (8)	0.0009 (7)	0.0128 (7)	0.0070 (7)

S1—C1	1.6808 (16)	N1—H1N	0.84 (2)
O1—C4	1.3325 (17)	N1—H2N	0.88 (2)
O1—C5	1.4577 (19)	N2—H3N	0.85 (2)
O2—C4	1.2069 (17)	C3—H3A	0.9600
N3—C2	1.2860 (17)	C3—H3B	0.9600
N3—N2	1.3675 (17)	C3—H3C	0.9600
N2—C1	1.3745 (17)	C5—H5A	0.9700
N1—C1	1.3217 (19)	C5—H5B	0.9700
C2—C3	1.4989 (19)	C6—H6A	0.9600
C2—C4	1.501 (2)	C6—H6B	0.9600
C6—C5	1.503 (2)	C6—H6C	0.9600
C4—O1—C5	115.86 (11)	C2—C3—H3A	109.00
C2—N3—N2	119.23 (12)	C2—C3—H3B	109.00
N3—N2—C1	118.06 (11)	C2—C3—H3C	109.00
N3—C2—C3	127.72 (14)	H3A—C3—H3B	109.00
N3—C2—C4	115.25 (12)	H3A—C3—H3C	109.00
C3—C2—C4	117.00 (12)	H3B—C3—H3C	109.00
N1—C1—N2	116.55 (13)	O1—C5—H5A	110.00
N1—C1—S1	123.64 (11)	O1—C5—H5B	110.00
N2—C1—S1	119.80 (11)	C6—C5—H5A	110.00
O2—C4—O1	123.40 (14)	C6—C5—H5B	110.00
O2—C4—C2	122.77 (13)	H5A—C5—H5B	108.00
O1—C4—C2	113.83 (11)	C5—C6—H6A	109.00
O1—C5—C6	107.52 (14)	C5—C6—H6B	109.00
C1—N1—H1N	118.9 (17)	C5—C6—H6C	109.00
C1—N1—H2N	119.2 (15)	H6A—C6—H6B	109.00
H1N—N1—H2N	122 (2)	H6A—C6—H6C	109.00
C1—N2—H3N	116.4 (12)	H6B—C6—H6C	109.00
N3—N2—H3N	125.5 (12)
C5—O1—C4—O2	−2.7 (2)	N2—N3—C2—C3	−0.6 (2)
C5—O1—C4—C2	176.48 (14)	N2—N3—C2—C4	−178.40 (13)
C4—O1—C5—C6	−178.14 (15)	N3—C2—C4—O1	4.43 (19)
C1—N2—N3—C2	177.04 (14)	N3—C2—C4—O2	−176.40 (15)
N3—N2—C1—S1	−174.66 (11)	C3—C2—C4—O1	−173.59 (15)
N3—N2—C1—N1	4.4 (2)	C3—C2—C4—O2	5.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N3	0.84 (2)	2.24 (2)	2.610 (2)	107 (2)
N1—H2N···O2i	0.88 (3)	2.08 (3)	2.954 (2)	172 (2)
N2—H3N···S1ii	0.85 (2)	2.78 (2)	3.623 (2)	172 (2)
C3—H3C···S1ii	0.96	2.82	3.611 (2)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N3	0.84 (2)	2.24 (2)	2.610 (2)	107 (2)
N1—H2N⋯O2i	0.88 (3)	2.08 (3)	2.954 (2)	172 (2)
N2—H3N⋯S1ii	0.85 (2)	2.78 (2)	3.623 (2)	172 (2)
C3—H3C⋯S1ii	0.96	2.82	3.611 (2)	141

Symmetry codes: (i) ; (ii) .