Crystal structure of 4,6-di­amino-2-sulfanyl­idene-1,2-di­hydro­pyridine-3-carbo­nitrile

Mohamed, S.K.; Akkurt, M.; Singh, K.; Hussein, B.R.M.; Albayati, M.R.

doi:10.1107/S1600536814018029

organic compounds

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Volume 70| Part 9| September 2014| Pages o993-o994

doi:10.1107/S1600536814018029

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Crystal structure of 4,6-diamino-2-sulfanylidene-1,2-dihydropyridine-3-carbonitrile

Shaaban K. Mohamed,^a,^b Mehmet Akkurt,^c Kuldip Singh,^d Bahgat R. M. Hussein ^e and Mustafa R. Albayati ^f ^*

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^dDepartment of Chemistry, University of Leicester, Leicester, England, ^eChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by P. C. Healy, Griffith University, Australia (Received 18 July 2014; accepted 6 August 2014; online 9 August 2014)

The title compound, C₆H₆N₄S, crystallizes with two independent molecules, A and B, in the asymmetric unit. Both independent molecules are almost planar [maximum deviations of 0.068 (6) Å in molecule A and 0.079 (6) Å in molecule B]. In the crystal, molecules A and B are linked by N—H⋯S, N—H⋯N and C—H⋯S hydrogen bonds, forming a three-dimensional network.

Keywords: crystal structure; polyfuntional pyridines; 3-cyanopyridine-2(1H)-thiones; hydrogen bonding.

CCDC reference: 1018166

1. Related literature

For the synthesis of polyfuntional pyridines, see: Attaby et al. (1995 ); Asadov et al. (2003 ). For various biological properties of pyridine scaffold compounds, see: Abdel-Rahman et al. (2002 ); Rao et al. (2006 ). For the synthesis of 3-cyanopyridine-2(1H)-thiones, see: Fahmy & Mohareb (1986 ); Schmidt & Kubitzek (1960 ). For the use of 3-cyanopyridine-2(1H)-thiones in the synthesis of bio-active compounds, see: Taylor et al. (1983 ); Gangiee et al. (1991 ); Amr et al. (2003 ); Abu-Shanab et al. (2002 ); Awad et al. (1962 ); El-Gaby (2004 ); Miky & Zahkoug (1997 ; Guerrera et al. (1993 ); Krauze et al. (1999 ). For a similar crystal structure, see: Eyduran et al. (2007 ). For the synthesis of the title compound, see: Abu-Shanab (1999 ). For standard bond-length data, see: Allen et al. (1987 ).

2. Experimental

2.1. Crystal data

C₆H₆N₄S
M_r = 166.21
Orthorhombic, P c a 2₁
a = 26.252 (8) Å
b = 4.3670 (14) Å
c = 12.523 (4) Å
V = 1435.7 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 150 K
0.32 × 0.12 × 0.04 mm

2.2. Data collection

Bruker APEX 2000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS: Bruker, 2011 ) T_min = 0.518, T_max = 0.928
11662 measured reflections
3412 independent reflections
2027 reflections with I > 2σ(I)
R_int = 0.137

2.3. Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.117
S = 0.87
3412 reflections
199 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.34 e Å⁻³
Absolute structure: Flack (1983 ), 1573 Friedel pairs
Absolute structure parameter: 0.01 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1Aⁱ	0.88	2.44	3.293 (5)	163
N1A—H1A⋯S1ⁱⁱ	0.88	2.80	3.579 (5)	149
N3—H31⋯N4Aⁱⁱⁱ	0.88	2.44	3.300 (8)	165
N3—H32⋯N2A^iv	0.88	2.39	3.077 (8)	135
N3A—H33⋯S1Aⁱⁱ	0.88	2.53	3.392 (6)	168
N3A—H34⋯N2^v	0.88	2.20	2.981 (8)	148
N4—H41⋯S1Aⁱ	0.88	2.75	3.536 (6)	149
N4—H42⋯S1^vi	0.88	2.63	3.424 (6)	151
N4—H42⋯N2^vi	0.88	2.62	3.083 (9)	114
N4A—H44⋯S1ⁱⁱ	0.88	2.53	3.353 (6)	157
C4—H4⋯S1^vi	0.95	2.74	3.551 (8)	143
Symmetry codes: (i) $[-x+1, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, -y+2, z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+1, z-1]$ ; (iv) $[-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ ; (v) $[-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}]$ ; (vi) $[-x+{\script{1\over 2}}, y-1, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1018166

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814018029/hg5399sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018029/hg5399Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018029/hg5399Isup3.cml

checkCIF report

Comment top

Polyfunctional pyridines are highly reactive reagents that have been used extensively in heterocyclic synthesis (Attaby et al., 1995; Asadov et al., 2003). 3-Cyano-pyridine-2(1H)-thiones compounds (Fahmy & Mohareb 1986; Schmidt & Kubitzek, 1960) have also gained considerable interest due to their importance as intermediates for the synthesis of the biologically active deazafolic acid and deaza amino protein ring system (Taylor et al., 1983; Gangiee et al., 1991). In addition, 3-Cyano-2(1H)-pyridinethiones and their related compounds were found to be very reactive substances for the synthesis of many different heterocyclic systems which exhibited biological activities such as antibacterial, pesticidal, antifungal, acaricidal and neurotropic activities (Amr et al., 2003; Abu-Shanab et al., 2002; Awad et al., 1962; El-Gaby, 2004; Miky & Zahkoug, 1997; Guerrera et al., 1993; Krauze et al., 1999; Abdel-Rahman et al., 2002; Rao et al., 2006). In light of these observations we report in this study the synthesis and crystal structure of the title compound.

In the title compound (Fig. 1), the asymmetric unit contains two independent molecules (A and B). Molecules A and B both are almost planar (Fig. 3), with the maximum deviations of -0.068 (6) Å for N4 in molecule A and 0.079 (6) Å for N2A in molecule B. The bond lengths of molecules A and B are comparable to those of the previously published structures (Eyduran et al., 2007; Allen et al., 1987).

In the crystal, the N—H···S, N—H···N and C—H···S hydrogen bonds connect the molecules, forming a three dimensional network (Table 1, Fig. 2). In addition, C—H···π interactions and π-π stacking interactions are not observed.

Related literature top

For the synthesis of polyfuntional pyridines, see: Attaby et al. (1995); Asadov et al. (2003). For various biological properties of pyridine scaffold compounds, see: Abdel-Rahman et al. (2002); Rao et al. (2006). For the synthesis of 3-cyanopyridine-2(1H)-thiones, see: Fahmy & Mohareb (1986); Schmidt & Kubitzek (1960). For the use of 3-cyanopyridine-2(1H)-thiones in the synthesis of bio-active compounds, see: Taylor et al. (1983); Gangiee et al. (1991); Amr et al. (2003); Abu-Shanab et al. (2002); Awad et al. (1962); El-Gaby (2004); Miky & Zahkoug (1997; Guerrera et al. (1993); Krauze et al. (1999). For a similar crystal structure, see: Eyduran et al. (2007). For the synthesis of the title compound, see: Abu-Shanab (1999). For standard bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared according to the reported method (Abu-Shanab, 1999). Crystals of the product were obtained in excellent yield (79%) and recrystallized from butanol to afford yellow needles (M.p. 583 K) in a sufficient quality for X-ray diffraction studies.

Computing details top

Data collection: SMART (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The title molecule showing the numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing viewed down the b axis showing the hydrogen bonding as dashed lines.

4,6-Diamino-2-sulfanylidene-1,2-dihydropyridine-3-carbonitrile top

Crystal data top

C₆H₆N₄S	F(000) = 688
M_r = 166.21	D_x = 1.538 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 748 reflections
a = 26.252 (8) Å	θ = 2.3–23.4°
b = 4.3670 (14) Å	µ = 0.38 mm⁻¹
c = 12.523 (4) Å	T = 150 K
V = 1435.7 (8) Å³	Needle, pale yellow
Z = 8	0.32 × 0.12 × 0.04 mm

Data collection top

Bruker APEX 2000 CCD area-detector diffractometer	3412 independent reflections
Radiation source: fine-focus sealed tube	2027 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.137
phi and ω scans	θ_max = 28.7°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS: Bruker, 2011)	h = −34→33
T_min = 0.518, T_max = 0.928	k = −5→5
11662 measured reflections	l = −16→16

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.064	w = 1/[σ²(F_o²) + (0.0282P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.117	(Δ/σ)_max < 0.001
S = 0.87	Δρ_max = 0.42 e Å⁻³
3412 reflections	Δρ_min = −0.34 e Å⁻³
199 parameters	Absolute structure: Flack (1983), 1573 Friedel pairs
1 restraint	Absolute structure parameter: 0.01 (13)

Crystal data top

C₆H₆N₄S	V = 1435.7 (8) Å³
M_r = 166.21	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 26.252 (8) Å	µ = 0.38 mm⁻¹
b = 4.3670 (14) Å	T = 150 K
c = 12.523 (4) Å	0.32 × 0.12 × 0.04 mm

Data collection top

Bruker APEX 2000 CCD area-detector diffractometer	3412 independent reflections
Absorption correction: multi-scan (SADABS: Bruker, 2011)	2027 reflections with I > 2σ(I)
T_min = 0.518, T_max = 0.928	R_int = 0.137
11662 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	H-atom parameters constrained
wR(F²) = 0.117	Δρ_max = 0.42 e Å⁻³
S = 0.87	Δρ_min = −0.34 e Å⁻³
3412 reflections	Absolute structure: Flack (1983), 1573 Friedel pairs
199 parameters	Absolute structure parameter: 0.01 (13)
1 restraint

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.27967 (6)	0.5692 (5)	0.10895 (15)	0.0332 (6)
S1A	0.59399 (6)	0.7628 (4)	0.41599 (15)	0.0279 (5)
N1	0.28114 (18)	0.2124 (13)	−0.0607 (4)	0.027 (2)
N2	0.1365 (2)	0.4860 (15)	0.1504 (5)	0.039 (2)
N3	0.1288 (2)	0.0258 (14)	−0.0735 (5)	0.037 (2)
N4	0.2980 (2)	−0.1066 (15)	−0.2027 (5)	0.040 (2)
C1	0.2513 (3)	0.3403 (15)	0.0166 (5)	0.026 (2)
C2	0.1995 (2)	0.2719 (16)	0.0115 (5)	0.025 (2)
C3	0.1797 (2)	0.0835 (15)	−0.0684 (5)	0.025 (2)
C4	0.2122 (2)	−0.0471 (17)	−0.1416 (6)	0.030 (3)
C5	0.2637 (2)	0.0167 (17)	−0.1372 (6)	0.027 (3)
C6	0.1661 (2)	0.3946 (18)	0.0905 (6)	0.031 (3)
N1A	0.59425 (19)	1.1254 (12)	0.5874 (4)	0.0230 (17)
N2A	0.4628 (2)	0.4521 (15)	0.4637 (5)	0.038 (2)
N3A	0.45527 (19)	0.8585 (13)	0.7032 (4)	0.0327 (19)
N4A	0.6065 (2)	1.4593 (13)	0.7299 (4)	0.0277 (19)
C1A	0.5677 (3)	0.9133 (16)	0.5295 (5)	0.025 (2)
C2A	0.5201 (2)	0.8249 (16)	0.5670 (5)	0.023 (2)
C3A	0.5005 (3)	0.9504 (16)	0.6643 (5)	0.022 (2)
C4A	0.5300 (2)	1.1636 (15)	0.7195 (6)	0.026 (2)
C5A	0.5760 (2)	1.2555 (16)	0.6797 (5)	0.026 (2)
C6A	0.4896 (2)	0.6151 (16)	0.5089 (6)	0.025 (2)
H1	0.31370	0.25940	−0.06120	0.0320*
H4	0.19930	−0.18060	−0.19500	0.0360*
H31	0.11670	−0.09500	−0.12370	0.0450*
H32	0.10800	0.10930	−0.02670	0.0450*
H41	0.33050	−0.06070	−0.19550	0.0480*
H42	0.28820	−0.23400	−0.25310	0.0480*
H1A	0.62450	1.18140	0.56440	0.0270*
H4A	0.51800	1.24540	0.78520	0.0310*
H33	0.44400	0.93300	0.76400	0.0400*
H34	0.43690	0.72390	0.66770	0.0400*
H43	0.59690	1.53930	0.79120	0.0330*
H44	0.63580	1.51200	0.70130	0.0330*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0253 (9)	0.0437 (12)	0.0307 (10)	−0.0029 (9)	−0.0017 (8)	−0.0139 (10)
S1A	0.0223 (8)	0.0385 (10)	0.0229 (8)	0.0018 (9)	0.0020 (8)	0.0010 (9)
N1	0.016 (3)	0.037 (4)	0.027 (4)	−0.001 (3)	−0.001 (2)	−0.005 (3)
N2	0.026 (3)	0.054 (5)	0.037 (4)	0.002 (3)	−0.001 (3)	−0.011 (3)
N3	0.024 (3)	0.054 (4)	0.034 (4)	−0.004 (3)	−0.002 (3)	−0.020 (4)
N4	0.029 (3)	0.057 (5)	0.034 (4)	−0.009 (3)	0.004 (3)	−0.020 (3)
C1	0.031 (4)	0.025 (4)	0.021 (4)	0.003 (3)	0.000 (3)	−0.001 (3)
C2	0.023 (4)	0.031 (4)	0.021 (4)	0.005 (3)	−0.003 (3)	−0.006 (3)
C3	0.022 (3)	0.028 (4)	0.025 (4)	−0.002 (3)	0.001 (3)	−0.001 (4)
C4	0.025 (4)	0.034 (5)	0.030 (4)	−0.005 (3)	0.000 (3)	−0.017 (4)
C5	0.026 (4)	0.036 (5)	0.020 (4)	−0.003 (3)	0.001 (3)	−0.008 (3)
C6	0.023 (4)	0.040 (5)	0.031 (5)	0.001 (3)	−0.001 (3)	−0.007 (4)
N1A	0.022 (3)	0.027 (3)	0.020 (3)	−0.003 (3)	−0.001 (2)	0.002 (3)
N2A	0.035 (4)	0.042 (4)	0.036 (4)	−0.009 (3)	0.001 (3)	−0.003 (3)
N3A	0.021 (3)	0.049 (4)	0.028 (3)	−0.004 (3)	0.005 (3)	−0.012 (3)
N4A	0.026 (3)	0.032 (4)	0.025 (3)	−0.003 (3)	−0.002 (2)	0.000 (3)
C1A	0.028 (4)	0.023 (4)	0.023 (4)	0.004 (3)	−0.003 (3)	0.001 (3)
C2A	0.019 (3)	0.026 (4)	0.025 (4)	0.002 (3)	−0.002 (3)	0.004 (3)
C3A	0.018 (3)	0.026 (4)	0.023 (4)	0.006 (3)	0.000 (3)	0.003 (3)
C4A	0.027 (4)	0.025 (4)	0.026 (4)	0.002 (3)	0.001 (3)	−0.001 (3)
C5A	0.023 (4)	0.026 (4)	0.030 (4)	0.000 (3)	−0.008 (3)	0.009 (4)
C6A	0.020 (4)	0.024 (4)	0.032 (4)	0.006 (3)	0.005 (3)	0.007 (4)

Geometric parameters (Å, º) top

S1—C1	1.700 (7)	N1A—C5A	1.374 (8)
S1A—C1A	1.711 (7)	N1A—C1A	1.367 (9)
N1—C1	1.365 (9)	N2A—C6A	1.150 (9)
N1—C5	1.363 (9)	N3A—C3A	1.345 (9)
N2—C6	1.151 (9)	C4—H4	0.9500
N3—C3	1.361 (7)	N4A—C5A	1.352 (8)
N4—C5	1.332 (9)	C1A—C2A	1.390 (9)
C1—C2	1.394 (9)	N1A—H1A	0.8800
N1—H1	0.8800	C2A—C3A	1.432 (9)
C2—C3	1.396 (9)	C2A—C6A	1.418 (9)
C2—C6	1.426 (9)	C3A—C4A	1.394 (10)
C3—C4	1.376 (9)	N3A—H34	0.8800
N3—H31	0.8800	N3A—H33	0.8800
N3—H32	0.8800	C4A—C5A	1.367 (8)
N4—H41	0.8800	N4A—H43	0.8800
N4—H42	0.8800	N4A—H44	0.8800
C4—C5	1.382 (8)	C4A—H4A	0.9500

C1—N1—C5	124.2 (5)	C5—C4—H4	120.00
S1—C1—N1	118.1 (6)	S1A—C1A—N1A	119.7 (5)
S1—C1—C2	125.8 (5)	S1A—C1A—C2A	122.5 (5)
N1—C1—C2	116.1 (6)	N1A—C1A—C2A	117.9 (6)
C1—N1—H1	118.00	C1A—N1A—H1A	118.00
C5—N1—H1	118.00	C5A—N1A—H1A	118.00
C1—C2—C3	121.5 (6)	C1A—C2A—C3A	120.3 (6)
C1—C2—C6	119.2 (6)	C1A—C2A—C6A	120.9 (6)
C3—C2—C6	119.3 (5)	C3A—C2A—C6A	118.8 (6)
N3—C3—C2	120.6 (5)	N3A—C3A—C2A	120.8 (6)
C3—N3—H31	120.00	C3A—N3A—H33	120.00
C3—N3—H32	120.00	C3A—N3A—H34	120.00
H31—N3—H32	120.00	H33—N3A—H34	120.00
C2—C3—C4	119.4 (5)	C2A—C3A—C4A	118.6 (6)
N3—C3—C4	120.0 (6)	N3A—C3A—C4A	120.7 (6)
C5—N4—H42	120.00	C5A—N4A—H44	120.00
C5—N4—H41	120.00	C5A—N4A—H43	120.00
C3—C4—C5	119.8 (6)	C3A—C4A—C5A	120.4 (7)
H41—N4—H42	120.00	H43—N4A—H44	120.00
N1—C5—N4	117.3 (5)	N1A—C5A—N4A	117.2 (5)
N4—C5—C4	123.8 (7)	N4A—C5A—C4A	123.2 (6)
N1—C5—C4	118.9 (6)	N1A—C5A—C4A	119.6 (6)
N2—C6—C2	175.5 (7)	N2A—C6A—C2A	176.7 (6)
C1A—N1A—C5A	123.3 (5)	C3A—C4A—H4A	120.00
C3—C4—H4	120.00	C5A—C4A—H4A	120.00

C5—N1—C1—S1	177.7 (5)	C5A—N1A—C1A—S1A	−179.5 (5)
C5—N1—C1—C2	−3.0 (10)	C5A—N1A—C1A—C2A	−0.5 (10)
C1—N1—C5—C4	3.5 (10)	C1A—N1A—C5A—C4A	2.6 (9)
C1—N1—C5—N4	−175.4 (6)	C1A—N1A—C5A—N4A	179.1 (6)
S1—C1—C2—C6	−1.5 (10)	S1A—C1A—C2A—C6A	−3.5 (10)
S1—C1—C2—C3	179.3 (5)	S1A—C1A—C2A—C3A	178.0 (5)
N1—C1—C2—C3	0.0 (10)	N1A—C1A—C2A—C3A	−1.1 (10)
N1—C1—C2—C6	179.2 (6)	N1A—C1A—C2A—C6A	177.5 (6)
C1—C2—C3—N3	−178.3 (6)	C1A—C2A—C3A—N3A	−177.7 (6)
C6—C2—C3—C4	−176.9 (7)	C6A—C2A—C3A—C4A	−178.1 (6)
C1—C2—C3—C4	2.4 (10)	C1A—C2A—C3A—C4A	0.5 (10)
C6—C2—C3—N3	2.4 (10)	C6A—C2A—C3A—N3A	3.7 (10)
N3—C3—C4—C5	178.8 (7)	N3A—C3A—C4A—C5A	179.8 (6)
C2—C3—C4—C5	−1.9 (10)	C2A—C3A—C4A—C5A	1.6 (10)
C3—C4—C5—N4	177.9 (7)	C3A—C4A—C5A—N4A	−179.4 (6)
C3—C4—C5—N1	−0.9 (11)	C3A—C4A—C5A—N1A	−3.2 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1Aⁱ	0.88	2.44	3.293 (5)	163
N1A—H1A···S1ⁱⁱ	0.88	2.80	3.579 (5)	149
N3—H31···N4Aⁱⁱⁱ	0.88	2.44	3.300 (8)	165
N3—H32···N2A^iv	0.88	2.39	3.077 (8)	135
N3A—H33···S1Aⁱⁱ	0.88	2.53	3.392 (6)	168
N3A—H34···N2^v	0.88	2.20	2.981 (8)	148
N4—H41···S1Aⁱ	0.88	2.75	3.536 (6)	149
N4—H42···S1^vi	0.88	2.63	3.424 (6)	151
N4—H42···N2^vi	0.88	2.62	3.083 (9)	114
N4A—H44···S1ⁱⁱ	0.88	2.53	3.353 (6)	157
C4—H4···S1^vi	0.95	2.74	3.551 (8)	143

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1Aⁱ	0.88	2.44	3.293 (5)	163
N1A—H1A···S1ⁱⁱ	0.88	2.80	3.579 (5)	149
N3—H31···N4Aⁱⁱⁱ	0.88	2.44	3.300 (8)	165
N3—H32···N2A^iv	0.88	2.39	3.077 (8)	135
N3A—H33···S1Aⁱⁱ	0.88	2.53	3.392 (6)	168
N3A—H34···N2^v	0.88	2.20	2.981 (8)	148
N4—H41···S1Aⁱ	0.88	2.75	3.536 (6)	149
N4—H42···S1^vi	0.88	2.63	3.424 (6)	151
N4—H42···N2^vi	0.88	2.62	3.083 (9)	114
N4A—H44···S1ⁱⁱ	0.88	2.53	3.353 (6)	157
C4—H4···S1^vi	0.95	2.74	3.551 (8)	143

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

Acknowledgements

Manchester Metropolitan University, Erciyes University and the University of Leicester are gratefully acknowledged for supporting this study.

References

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Volume 70| Part 9| September 2014| Pages o993-o994

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 4,6-di­amino-2-sulfanyl­­idene-1,2-di­hydro­pyridine-3-carbo­nitrile

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 4,6-diamino-2-sulfanylidene-1,2-dihydropyridine-3-carbonitrile