2-Sulfanyl-idene-1,2-dihydro-pyridine-3-carbohydrazide.

All non-H atoms of the title compound, C(6)H(7)N(3)OS, which exists in the thione form, lie in a common plane (r.m.s. of non-H atoms = 0.08 Å). The amino group of the -NH-NH(2) substituent forms an intra-molecular hydrogen bond to the S atom. The terminal -NH(2) group is pyramidally coordinated; it forms a weak N-H⋯O and a weak N-H⋯S hydrogen bond. Furthermore, the N atom is an acceptor for a C-H⋯N contact. The amino group of the ring is a hydrogen-bond donor to the carbonyl O atom of an adjacent mol-ecule, this inter-action giving rise to a linear chain motif running along the b axis.

Related literature

For the synthesis of 3-mercaptonicotinoylhydrazide from 3-mercaptonicotinic acid, see: Katz et al. (1958 ▶). For the synthesis of 2-(3,5-di-tert-butyl-4-hydroxybenzylsulfanyl)nicotinic acid, see: Mansor et al. (2008 ▶).

Experimental

Crystal data

C6H7N3OS

M = 169.21

Triclinic,

a = 7.1952 (2) Å

b = 7.4279 (2) Å

c = 7.7492 (2) Å

α = 88.205 (2)°

β = 64.201 (2)°

γ = 72.072 (2)°

V = 352.22 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.40 mm−1

T = 123 K

0.35 × 0.05 × 0.01 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.874, T max = 0.996

3311 measured reflections

1619 independent reflections

1391 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.090

S = 1.08

1619 reflections

128 parameters

7 restraints

All H-atom parameters refined

Δρmax = 0.67 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681003521X/bt5335sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003521X/bt5335Isup2.hkl

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

C6H7N3OS	Z = 2
Mr = 169.21	F(000) = 176
Triclinic, P1	Dx = 1.595 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1952 (2) Å	Cell parameters from 1745 reflections
b = 7.4279 (2) Å	θ = 2.9–28.3°
c = 7.7492 (2) Å	µ = 0.40 mm−1
α = 88.205 (2)°	T = 123 K
β = 64.201 (2)°	Plate, orange
γ = 72.072 (2)°	0.35 × 0.05 × 0.01 mm
V = 352.22 (2) Å3

Bruker SMART APEX diffractometer	1619 independent reflections
Radiation source: fine-focus sealed tube	1391 reflections with I > 2σ(I)
graphite	Rint = 0.015
ω scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.874, Tmax = 0.996	k = −9→9
3311 measured reflections	l = −10→10

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	All H-atom parameters refined
S = 1.08	w = 1/[σ2(Fo2) + (0.0372P)2 + 0.3308P] where P = (Fo2 + 2Fc2)/3
1619 reflections	(Δ/σ)max = 0.001
128 parameters	Δρmax = 0.67 e Å−3
7 restraints	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.58477 (8)	0.32161 (7)	0.76922 (7)	0.02102 (15)
O1	0.7744 (2)	0.81569 (18)	0.44198 (19)	0.0210 (3)
N1	0.8505 (3)	0.1589 (2)	0.4153 (2)	0.0165 (3)
N2	0.5443 (3)	0.7318 (2)	0.7129 (2)	0.0191 (3)
N3	0.4375 (3)	0.9211 (2)	0.8063 (2)	0.0218 (4)
C1	1.0002 (3)	0.1308 (3)	0.2289 (3)	0.0182 (4)
C2	1.0636 (3)	0.2790 (3)	0.1432 (3)	0.0199 (4)
C3	0.9635 (3)	0.4575 (3)	0.2526 (3)	0.0181 (4)
C4	0.8069 (3)	0.4870 (2)	0.4421 (3)	0.0147 (4)
C5	0.7505 (3)	0.3285 (2)	0.5345 (3)	0.0148 (4)
C6	0.7070 (3)	0.6906 (2)	0.5353 (3)	0.0160 (4)
H1	0.805 (4)	0.064 (3)	0.466 (3)	0.036 (7)*
H2	0.505 (4)	0.638 (3)	0.776 (3)	0.039 (7)*
H3	0.404 (4)	0.991 (3)	0.724 (3)	0.036 (7)*
H4	0.533 (3)	0.956 (4)	0.827 (4)	0.032 (7)*
H1A	1.059 (3)	0.0051 (17)	0.165 (3)	0.020 (5)*
H2A	1.171 (3)	0.260 (3)	0.0141 (17)	0.027 (6)*
H3A	1.002 (4)	0.565 (2)	0.199 (3)	0.021 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0251 (3)	0.0148 (2)	0.0172 (2)	−0.00847 (18)	−0.00306 (19)	0.00297 (16)
O1	0.0259 (7)	0.0123 (6)	0.0214 (7)	−0.0081 (5)	−0.0063 (6)	0.0033 (5)
N1	0.0190 (8)	0.0107 (7)	0.0189 (8)	−0.0055 (6)	−0.0072 (6)	0.0025 (6)
N2	0.0210 (8)	0.0102 (7)	0.0194 (8)	−0.0041 (6)	−0.0039 (7)	−0.0003 (6)
N3	0.0250 (9)	0.0114 (7)	0.0216 (8)	−0.0023 (6)	−0.0061 (7)	−0.0017 (6)
C1	0.0199 (9)	0.0125 (8)	0.0192 (9)	−0.0020 (7)	−0.0080 (8)	−0.0016 (7)
C2	0.0196 (9)	0.0176 (9)	0.0161 (9)	−0.0041 (7)	−0.0036 (7)	0.0011 (7)
C3	0.0208 (9)	0.0138 (8)	0.0200 (9)	−0.0065 (7)	−0.0090 (8)	0.0047 (7)
C4	0.0155 (8)	0.0110 (8)	0.0171 (8)	−0.0034 (7)	−0.0075 (7)	0.0016 (6)
C5	0.0143 (8)	0.0137 (8)	0.0160 (8)	−0.0041 (7)	−0.0067 (7)	0.0016 (7)
C6	0.0163 (8)	0.0125 (8)	0.0199 (9)	−0.0041 (7)	−0.0091 (7)	0.0023 (7)

S1—C5	1.696 (2)	N3—H4	0.88 (1)
O1—C6	1.246 (2)	C1—C2	1.365 (3)
N1—C1	1.348 (2)	C1—H1A	0.95 (1)
N1—C5	1.376 (2)	C2—C3	1.395 (3)
N1—H1	0.88 (1)	C2—H2A	0.94 (1)
N2—C6	1.327 (2)	C3—C4	1.380 (3)
N2—N3	1.416 (2)	C3—H3A	0.95 (1)
N2—H2	0.89 (1)	C4—C5	1.433 (2)
N3—H3	0.88 (1)	C4—C6	1.507 (2)
C1—N1—C5	125.85 (15)	C3—C2—H2A	121.7 (14)
C1—N1—H1	118.5 (17)	C4—C3—C2	122.34 (17)
C5—N1—H1	115.6 (17)	C4—C3—H3A	116.8 (14)
C6—N2—N3	121.63 (15)	C2—C3—H3A	120.9 (14)
C6—N2—H2	119.0 (17)	C3—C4—C5	119.45 (16)
N3—N2—H2	119.3 (17)	C3—C4—C6	115.35 (15)
N2—N3—H3	106.3 (17)	C5—C4—C6	125.20 (16)
N2—N3—H4	107.0 (17)	N1—C5—C4	114.58 (15)
H3—N3—H4	109 (2)	N1—C5—S1	116.57 (13)
N1—C1—C2	119.76 (16)	C4—C5—S1	128.82 (14)
N1—C1—H1A	116.8 (14)	O1—C6—N2	121.97 (16)
C2—C1—H1A	123.4 (14)	O1—C6—C4	119.33 (16)
C1—C2—C3	117.83 (17)	N2—C6—C4	118.66 (15)
C1—C2—H2A	120.5 (14)
C5—N1—C1—C2	−0.3 (3)	C3—C4—C5—S1	173.23 (15)
N1—C1—C2—C3	−2.1 (3)	C6—C4—C5—S1	−7.1 (3)
C1—C2—C3—C4	0.7 (3)	N3—N2—C6—O1	0.2 (3)
C2—C3—C4—C5	3.0 (3)	N3—N2—C6—C4	−177.57 (17)
C2—C3—C4—C6	−176.77 (17)	C3—C4—C6—O1	−2.5 (3)
C1—N1—C5—C4	3.8 (3)	C5—C4—C6—O1	177.77 (17)
C1—N1—C5—S1	−174.60 (15)	C3—C4—C6—N2	175.28 (17)
C3—C4—C5—N1	−4.9 (3)	C5—C4—C6—N2	−4.4 (3)
C6—C4—C5—N1	174.76 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88 (1)	1.95 (2)	2.751 (2)	152 (2)
N2—H2···S1	0.89 (1)	2.24 (2)	3.007 (2)	145 (2)
N3—H3···O1ii	0.88 (2)	2.36 (3)	3.214 (2)	166 (3)
N3—H4···S1iii	0.88 (3)	2.85 (3)	3.4173 (18)	124 (2)
C2—H2A···N3iv	0.94 (1)	2.69 (2)	3.323 (4)	125 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88 (1)	1.95 (2)	2.751 (2)	152 (2)
N2—H2⋯S1	0.89 (1)	2.24 (2)	3.007 (2)	145 (2)
N3—H3⋯O1ii	0.88 (2)	2.36 (3)	3.214 (2)	166 (3)
N3—H4⋯S1iii	0.88 (3)	2.85 (3)	3.4173 (18)	124 (2)
C2—H2A⋯N3iv	0.94 (1)	2.69 (2)	3.323 (4)	125 (2)

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