Crystal structure of N-[4-amino-5-cyano-6-(methyl­sulfan­yl)pyridin-2-yl]acetamide hemihydrate

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

doi:10.1107/S205698901500256X

organic compounds

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ISSN: 2056-9890

Volume 71| Part 3| March 2015| Pages o171-o172

doi:10.1107/S205698901500256X

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Crystal structure of N-[4-amino-5-cyano-6-(methylsulfanyl)pyridin-2-yl]acetamide hemihydrate

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

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Chemistry, The University of Tennessee at Chattanooga, Chattanooga, TN 37403, USA, ^cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^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 H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 4 February 2015; accepted 6 February 2015; online 13 February 2015)

The title compound, C₉H₁₀N₄OS·0.5H₂O, crystallizes with two independent molecules (A and B) in the asymmetric unit, together with a water molecule of crystallization. The acetamide moiety, which has an extended conformation, is inclined to the pyridine ring by 7.95 (16)° in molecule A and by 1.77 (16)° in molecule B. In the crystal, the A and B molecules are linked by two N—H⋯O_carbonyl hydrogen bonds, forming a dimer. The dimers are linked via N—H⋯N hydrogen bonds, forming ribbons that are linked by N—H⋯O_water hydrogen bonds to form sheets parallel to (110). The sheets are linked by O—H⋯N hydrogen bonds, forming slabs, and between the slabs there are weak slipped parallel π–π interactions [inter-centroid distance = 3.734 (2) Å, interplanar distance = 3.3505 (11) Å and slippage = 1.648 Å], forming a three-dimensional structure.

Keywords: crystal structure; poly-functional pyridines; acetamide; disorder; hydrogen bonding.

CCDC reference: 1048267

1. Related literature

For various applications of polyfunctional pyridines, see: Knyazhanskii et al. (1996 ); Kurfurst et al. (1989 ); Enyedy et al. (2003 ); Arora & Knaus (1999 ); Kim et al. 2004 ); Pillai et al. (2003 ).

2. Experimental

2.1. Crystal data

C₉H₁₀N₄OS·0.5H₂O
M_r = 231.28
Triclinic, $[P \overline 1]$
a = 8.229 (3) Å
b = 10.181 (4) Å
c = 13.198 (5) Å
α = 84.221 (10)°
β = 80.036 (10)°
γ = 82.136 (11)°
V = 1075.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 200 K
0.40 × 0.40 × 0.40 mm

2.2. Data collection

Bruker SMART X2S benchtop diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.813, T_max = 1.000
19554 measured reflections
3775 independent reflections
2517 reflections with I > 2σ(I)
R_int = 0.066

2.3. Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.150
S = 1.03
3775 reflections
305 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3AN⋯O2	0.88	2.00	2.870 (3)	169
N7—H7BN⋯O1	0.88	1.99	2.860 (3)	170
N3—H3BN⋯N8ⁱ	0.88	2.33	3.080 (4)	143
N7—H7AN⋯N4ⁱⁱ	0.88	2.38	3.116 (4)	142
N2—H2N⋯O3A	0.88	2.12	2.984 (10)	166
N2—H2N⋯O3B	0.88	2.21	3.079 (9)	172
N6—H6N⋯O3Aⁱⁱⁱ	0.88	2.26	3.138 (10)	173
N6—H6N⋯O3Bⁱⁱⁱ	0.88	2.19	3.051 (9)	166
O3A—H3A2⋯N7^iv	0.85 (2)	2.36 (6)	3.083 (12)	143 (9)
O3B—H3B1⋯N5^v	0.85 (2)	2.57 (6)	3.239 (8)	137 (8)
Symmetry codes: (i) x+1, y-1, z; (ii) x-1, y+1, z; (iii) x, y, z+1; (iv) -x+1, -y+1, -z; (v) x, y, z-1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL2014 and PLATON.

Supporting information

CCDC reference: 1048267

Crystal structure: contains datablocks global, I. DOI: 10.1107/S205698901500256X/su5077sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S205698901500256X/su5077Isup2.hkl

Supporting information file. DOI: 10.1107/S205698901500256X/su5077Isup3.cml

checkCIF report

Comment top

Poly-functional pyridines are an interesting class of compounds due to their optical properties (Knyazhanskii et al., 1996; Kurfurst et al., 1989), and their biological activities (Enyedy et al., 2003), such as anticonvulsants (Arora et al., 1999), antihistaminic reagents (Kim et al., 2004), and cardivascular disorder treatments (Pillai et al., 2003). In view of such facts we herein report on the synthesis and crystal structure of the new title poly-functional pyridine compound.

The asymmetric unit of the title compound, Fig. 1, contains two independent title molecules (A and B) and one water molecule. In molecule A the dihedral angle between the pyridine ring (N1/C1–C5) and the acetamide moiety (O1/N2(C7/C8) is 7.95 (16)°, while in molecule B the corresponding angle, involving the pyridine ring (N5/C10-C14) and actemide moiety (O2/N2/C7/C8), is 1.77 (16)°.

In the crystal, the A and B molecules are linked by two N-H···O_carbonyl hydrogen bonds forming a dimer (Table 1 and Fig. 1). The dimers are linked via N-H···N hydrogen bonds forming ribbons that are linked by N-H···O_water hydrogen bonds to form sheets parallel to (110); see Table 1. The sheets are linked by O-H···N hydrogen bonds forming slabs (Table 1). Between the slabs there are weak slipped parallel π-π interactions forming a three-dimensional structure, Fig. 2 [inter-centroid distance Cg1···Cg1ⁱ = 3.734 (2) Å, inter-planar distance = 3.351 (1) Å, slippage = 1.648 Å; Cg1 is the centroid of ring N5/C10-C14 (molecule B); symmetry code: (i) -x, -y+1, -z+1].

Related literature top

For various applications of polyfunctional pyridines, see: Knyazhanskii et al. (1996); Kurfurst et al. (1989); Enyedy et al. (2003); Arora & Knaus (1999); Kim et al. 2004); Pillai et al. (2003).

Experimental top

A solution of 0.5 g (2.7 mmol) of 4,6-diamino-3-cyano-2-methylthiopyridine-2(1H)-thione in 30 ml glacial acetic acid was refluxed for 3 h. The reaction mixture was allowed to cool and it was then poured into 100 ml of ice cold water. The formed precipitate was collected and dried under vacuum. Yellow crystals, suitable for X-ray analysis, were obtained by recrystallization of the solid product from ethanol (yield: 92%; m.p.: 523–525 K).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The N—H···O hydrogen bonds are shown as dashed lines (see Table 1 for details).
	Fig. 2. View along the c axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity).

N-[4-Amino-5-cyano-6-(methylsulfanyl)pyridin-2-yl]acetamide hemihydrate top

Crystal data top

C₉H₁₀N₄OS·0.5H₂O	Z = 4
M_r = 231.28	F(000) = 484
Triclinic, P1	D_x = 1.428 Mg m⁻³
a = 8.229 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.181 (4) Å	Cell parameters from 4579 reflections
c = 13.198 (5) Å	θ = 2.5–25.1°
α = 84.221 (10)°	µ = 0.29 mm⁻¹
β = 80.036 (10)°	T = 200 K
γ = 82.136 (11)°	Block, yellow
V = 1075.4 (7) Å³	0.40 × 0.40 × 0.40 mm

Data collection top

Bruker SMART X2S benchtop diffractometer	3775 independent reflections
Radiation source: XOS X-beam microfocus source	2517 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	R_int = 0.066
ω scans	θ_max = 25.2°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
T_min = 0.813, T_max = 1.000	k = −12→12
19554 measured reflections	l = −15→15

Refinement top

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)] = 0.052	Hydrogen site location: mixed
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0859P)² + 0.1759P] where P = (F_o² + 2F_c²)/3
3775 reflections	(Δ/σ)_max = 0.001
305 parameters	Δρ_max = 0.63 e Å⁻³
9 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₉H₁₀N₄OS·0.5H₂O	γ = 82.136 (11)°
M_r = 231.28	V = 1075.4 (7) Å³
Triclinic, P1	Z = 4
a = 8.229 (3) Å	Mo Kα radiation
b = 10.181 (4) Å	µ = 0.29 mm⁻¹
c = 13.198 (5) Å	T = 200 K
α = 84.221 (10)°	0.40 × 0.40 × 0.40 mm
β = 80.036 (10)°

Data collection top

Bruker SMART X2S benchtop diffractometer	3775 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2517 reflections with I > 2σ(I)
T_min = 0.813, T_max = 1.000	R_int = 0.066
19554 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	9 restraints
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.63 e Å⁻³
3775 reflections	Δρ_min = −0.31 e Å⁻³
305 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.84898 (9)	−0.09268 (8)	−0.11814 (5)	0.0324 (2)
O1	0.3621 (3)	0.3985 (2)	0.14350 (16)	0.0444 (6)
N1	0.6422 (3)	0.1137 (2)	−0.04595 (17)	0.0243 (5)
N2	0.4586 (3)	0.2943 (2)	−0.00302 (17)	0.0263 (6)
H2N	0.4539	0.3015	−0.0695	0.032*
N3	0.7191 (3)	0.0201 (3)	0.25778 (18)	0.0369 (7)
H3AN	0.6676	0.0723	0.3056	0.044*
H3BN	0.7858	−0.0510	0.2744	0.044*
N4	0.9584 (4)	−0.2438 (3)	0.1290 (2)	0.0453 (7)
C1	0.5671 (3)	0.1876 (3)	0.0309 (2)	0.0234 (6)
C2	0.5899 (3)	0.1621 (3)	0.1320 (2)	0.0267 (7)
H2	0.5348	0.2200	0.1827	0.032*
C3	0.6957 (3)	0.0492 (3)	0.1588 (2)	0.0263 (7)
C4	0.7727 (3)	−0.0312 (3)	0.0799 (2)	0.0224 (6)
C5	0.7434 (3)	0.0062 (3)	−0.0213 (2)	0.0229 (6)
C6	0.7793 (4)	−0.0068 (3)	−0.2309 (2)	0.0440 (9)
H6A	0.8123	0.0831	−0.2403	0.066*
H6B	0.6579	−0.0013	−0.2227	0.066*
H6C	0.8295	−0.0553	−0.2914	0.066*
C7	0.3596 (3)	0.3882 (3)	0.0525 (2)	0.0286 (7)
C8	0.2446 (4)	0.4802 (3)	−0.0064 (2)	0.0359 (8)
H8A	0.1873	0.5507	0.0368	0.054*
H8B	0.1626	0.4302	−0.0258	0.054*
H8C	0.3088	0.5199	−0.0688	0.054*
C9	0.8785 (4)	−0.1495 (3)	0.1042 (2)	0.0290 (7)
S2	0.05057 (10)	0.70420 (8)	0.65341 (6)	0.0356 (3)
O2	0.5272 (3)	0.2080 (2)	0.39329 (15)	0.0378 (5)
N5	0.2537 (3)	0.4955 (2)	0.58226 (16)	0.0215 (5)
N6	0.4339 (3)	0.3125 (2)	0.53944 (17)	0.0255 (5)
H6N	0.4420	0.3077	0.6053	0.031*
N7	0.1738 (3)	0.5867 (3)	0.27873 (18)	0.0362 (7)
H7AN	0.1079	0.6583	0.2620	0.043*
H7BN	0.2260	0.5349	0.2308	0.043*
N8	−0.0881 (3)	0.8386 (3)	0.4093 (2)	0.0424 (7)
C10	0.3278 (3)	0.4203 (3)	0.5052 (2)	0.0236 (6)
C11	0.3036 (3)	0.4451 (3)	0.4037 (2)	0.0256 (6)
H11	0.3597	0.3881	0.3526	0.031*
C12	0.1947 (3)	0.5562 (3)	0.3782 (2)	0.0240 (6)
C13	0.1145 (3)	0.6354 (3)	0.4567 (2)	0.0251 (7)
C14	0.1495 (3)	0.6013 (3)	0.5577 (2)	0.0251 (6)
C15	0.1416 (4)	0.6296 (3)	0.7623 (2)	0.0427 (9)
H15C	0.0914	0.6770	0.8233	0.064*
H15B	0.2615	0.6348	0.7486	0.064*
H15A	0.1216	0.5362	0.7747	0.064*
C16	0.5260 (3)	0.2144 (3)	0.4854 (2)	0.0262 (7)
C17	0.6252 (4)	0.1123 (3)	0.5476 (2)	0.0337 (7)
H17A	0.5529	0.0487	0.5854	0.051*
H17B	0.6719	0.1564	0.5967	0.051*
H17C	0.7157	0.0652	0.5014	0.051*
C18	0.0001 (4)	0.7485 (3)	0.4338 (2)	0.0298 (7)
O3A	0.4983 (13)	0.2878 (10)	−0.2316 (7)	0.066 (3)	0.5
H3A1	0.541 (6)	0.223 (3)	−0.2637 (16)	0.099*	0.5
H3A2	0.555 (10)	0.352 (5)	−0.254 (6)	0.099*	0.5
O3B	0.4470 (11)	0.3490 (9)	−0.2356 (7)	0.052 (2)	0.5
H3B1	0.383 (8)	0.416 (5)	−0.255 (7)	0.077*	0.5
H3B2	0.386 (8)	0.289 (6)	−0.214 (2)	0.077*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0361 (5)	0.0342 (5)	0.0234 (4)	0.0139 (4)	−0.0053 (3)	−0.0092 (3)
O1	0.0625 (15)	0.0445 (15)	0.0215 (12)	0.0279 (12)	−0.0163 (10)	−0.0105 (10)
N1	0.0268 (12)	0.0269 (14)	0.0176 (12)	0.0047 (11)	−0.0036 (10)	−0.0051 (10)
N2	0.0342 (13)	0.0255 (14)	0.0165 (12)	0.0124 (11)	−0.0094 (10)	−0.0014 (10)
N3	0.0503 (16)	0.0343 (16)	0.0206 (13)	0.0244 (13)	−0.0121 (11)	−0.0046 (11)
N4	0.0523 (17)	0.0385 (18)	0.0426 (17)	0.0174 (15)	−0.0188 (14)	−0.0031 (14)
C1	0.0246 (14)	0.0214 (15)	0.0222 (14)	0.0048 (12)	−0.0043 (11)	−0.0014 (12)
C2	0.0325 (15)	0.0264 (17)	0.0194 (14)	0.0093 (13)	−0.0059 (12)	−0.0069 (12)
C3	0.0306 (15)	0.0257 (17)	0.0226 (15)	0.0035 (13)	−0.0098 (12)	−0.0014 (12)
C4	0.0235 (14)	0.0223 (15)	0.0199 (14)	0.0059 (12)	−0.0051 (11)	−0.0040 (11)
C5	0.0217 (14)	0.0245 (16)	0.0226 (15)	0.0017 (12)	−0.0060 (11)	−0.0042 (12)
C6	0.054 (2)	0.049 (2)	0.0224 (16)	0.0151 (17)	−0.0047 (15)	−0.0050 (15)
C7	0.0321 (16)	0.0274 (17)	0.0244 (16)	0.0072 (13)	−0.0079 (13)	−0.0014 (13)
C8	0.0411 (18)	0.0340 (19)	0.0298 (17)	0.0164 (15)	−0.0111 (14)	−0.0085 (14)
C9	0.0347 (16)	0.0286 (18)	0.0233 (15)	0.0044 (15)	−0.0085 (13)	−0.0046 (13)
S2	0.0450 (5)	0.0339 (5)	0.0249 (4)	0.0171 (4)	−0.0098 (3)	−0.0110 (3)
O2	0.0507 (13)	0.0362 (13)	0.0234 (11)	0.0194 (10)	−0.0134 (10)	−0.0081 (9)
N5	0.0245 (12)	0.0211 (13)	0.0185 (12)	0.0055 (10)	−0.0059 (9)	−0.0061 (10)
N6	0.0319 (13)	0.0292 (14)	0.0139 (11)	0.0102 (11)	−0.0090 (10)	−0.0042 (10)
N7	0.0516 (16)	0.0314 (15)	0.0213 (13)	0.0178 (13)	−0.0114 (12)	−0.0028 (11)
N8	0.0465 (16)	0.0372 (17)	0.0392 (16)	0.0147 (14)	−0.0137 (13)	0.0030 (13)
C10	0.0263 (15)	0.0249 (16)	0.0189 (14)	0.0021 (13)	−0.0042 (11)	−0.0042 (12)
C11	0.0324 (15)	0.0262 (16)	0.0174 (14)	0.0078 (13)	−0.0071 (12)	−0.0072 (12)
C12	0.0286 (15)	0.0252 (16)	0.0184 (14)	0.0013 (13)	−0.0078 (11)	−0.0016 (12)
C13	0.0284 (15)	0.0213 (16)	0.0241 (15)	0.0080 (13)	−0.0084 (12)	−0.0030 (12)
C14	0.0279 (15)	0.0246 (16)	0.0222 (15)	0.0042 (13)	−0.0072 (12)	−0.0041 (12)
C15	0.056 (2)	0.046 (2)	0.0249 (16)	0.0141 (17)	−0.0152 (15)	−0.0120 (15)
C16	0.0281 (15)	0.0284 (17)	0.0219 (15)	0.0018 (13)	−0.0066 (12)	−0.0028 (13)
C17	0.0413 (18)	0.0279 (17)	0.0300 (17)	0.0108 (14)	−0.0107 (14)	−0.0044 (13)
C18	0.0358 (17)	0.0283 (18)	0.0238 (15)	0.0029 (15)	−0.0052 (13)	−0.0039 (13)
O3A	0.077 (7)	0.086 (8)	0.031 (3)	−0.003 (5)	0.002 (4)	−0.017 (5)
O3B	0.050 (5)	0.072 (6)	0.029 (3)	0.004 (4)	−0.006 (3)	−0.005 (4)

Geometric parameters (Å, º) top

S1—C5	1.743 (3)	O2—C16	1.222 (3)
S1—C6	1.790 (3)	N5—C14	1.332 (3)
O1—C7	1.219 (3)	N5—C10	1.345 (3)
N1—C5	1.330 (4)	N6—C16	1.353 (3)
N1—C1	1.336 (4)	N6—C10	1.394 (3)
N2—C7	1.356 (4)	N6—H6N	0.8800
N2—C1	1.398 (3)	N7—C12	1.353 (3)
N2—H2N	0.8800	N7—H7AN	0.8800
N3—C3	1.350 (3)	N7—H7BN	0.8800
N3—H3AN	0.8800	N8—C18	1.145 (4)
N3—H3BN	0.8800	C10—C11	1.381 (4)
N4—C9	1.140 (4)	C11—C12	1.395 (4)
C1—C2	1.374 (4)	C11—H11	0.9500
C2—C3	1.399 (4)	C12—C13	1.395 (4)
C2—H2	0.9500	C13—C14	1.411 (4)
C3—C4	1.399 (4)	C13—C18	1.427 (4)
C4—C5	1.403 (4)	C15—H15C	0.9800
C4—C9	1.430 (4)	C15—H15B	0.9800
C6—H6A	0.9800	C15—H15A	0.9800
C6—H6B	0.9800	C16—C17	1.500 (4)
C6—H6C	0.9800	C17—H17A	0.9800
C7—C8	1.497 (4)	C17—H17B	0.9800
C8—H8A	0.9800	C17—H17C	0.9800
C8—H8B	0.9800	O3A—H3A1	0.823 (18)
C8—H8C	0.9800	O3A—H3A2	0.85 (2)
S2—C14	1.742 (3)	O3B—H3B1	0.85 (2)
S2—C15	1.789 (3)	O3B—H3B2	0.84 (2)

C5—S1—C6	102.00 (14)	C14—N5—C10	116.8 (2)
C5—N1—C1	116.9 (2)	C16—N6—C10	129.0 (2)
C7—N2—C1	128.8 (2)	C16—N6—H6N	115.5
C7—N2—H2N	115.6	C10—N6—H6N	115.5
C1—N2—H2N	115.6	C12—N7—H7AN	120.0
C3—N3—H3AN	120.0	C12—N7—H7BN	120.0
C3—N3—H3BN	120.0	H7AN—N7—H7BN	120.0
H3AN—N3—H3BN	120.0	N5—C10—C11	124.8 (3)
N1—C1—C2	124.8 (3)	N5—C10—N6	111.9 (2)
N1—C1—N2	112.0 (2)	C11—C10—N6	123.2 (2)
C2—C1—N2	123.2 (3)	C10—C11—C12	118.2 (2)
C1—C2—C3	118.7 (3)	C10—C11—H11	120.9
C1—C2—H2	120.6	C12—C11—H11	120.9
C3—C2—H2	120.6	N7—C12—C13	122.0 (3)
N3—C3—C2	120.2 (3)	N7—C12—C11	119.7 (3)
N3—C3—C4	122.4 (3)	C13—C12—C11	118.3 (2)
C2—C3—C4	117.3 (2)	C12—C13—C14	118.7 (2)
C3—C4—C5	119.1 (2)	C12—C13—C18	119.8 (2)
C3—C4—C9	119.3 (2)	C14—C13—C18	121.5 (2)
C5—C4—C9	121.6 (2)	N5—C14—C13	123.2 (2)
N1—C5—C4	123.1 (2)	N5—C14—S2	119.3 (2)
N1—C5—S1	119.3 (2)	C13—C14—S2	117.6 (2)
C4—C5—S1	117.6 (2)	S2—C15—H15C	109.5
S1—C6—H6A	109.5	S2—C15—H15B	109.5
S1—C6—H6B	109.5	H15C—C15—H15B	109.5
H6A—C6—H6B	109.5	S2—C15—H15A	109.5
S1—C6—H6C	109.5	H15C—C15—H15A	109.5
H6A—C6—H6C	109.5	H15B—C15—H15A	109.5
H6B—C6—H6C	109.5	O2—C16—N6	122.9 (2)
O1—C7—N2	123.4 (2)	O2—C16—C17	122.4 (3)
O1—C7—C8	121.8 (3)	N6—C16—C17	114.8 (2)
N2—C7—C8	114.8 (2)	C16—C17—H17A	109.5
C7—C8—H8A	109.5	C16—C17—H17B	109.5
C7—C8—H8B	109.5	H17A—C17—H17B	109.5
H8A—C8—H8B	109.5	C16—C17—H17C	109.5
C7—C8—H8C	109.5	H17A—C17—H17C	109.5
H8A—C8—H8C	109.5	H17B—C17—H17C	109.5
H8B—C8—H8C	109.5	N8—C18—C13	176.0 (3)
N4—C9—C4	176.3 (3)	H3A1—O3A—H3A2	108 (3)
C14—S2—C15	101.47 (14)	H3B1—O3B—H3B2	106 (3)

C5—N1—C1—C2	1.5 (4)	C14—N5—C10—C11	0.1 (4)
C5—N1—C1—N2	−177.4 (2)	C14—N5—C10—N6	−180.0 (2)
C7—N2—C1—N1	178.7 (3)	C16—N6—C10—N5	178.3 (3)
C7—N2—C1—C2	−0.2 (5)	C16—N6—C10—C11	−1.7 (4)
N1—C1—C2—C3	−1.7 (4)	N5—C10—C11—C12	0.0 (4)
N2—C1—C2—C3	177.1 (3)	N6—C10—C11—C12	−179.9 (2)
C1—C2—C3—N3	−179.1 (3)	C10—C11—C12—N7	177.1 (3)
C1—C2—C3—C4	0.1 (4)	C10—C11—C12—C13	−0.8 (4)
N3—C3—C4—C5	−179.5 (3)	N7—C12—C13—C14	−176.5 (3)
C2—C3—C4—C5	1.4 (4)	C11—C12—C13—C14	1.3 (4)
N3—C3—C4—C9	0.8 (4)	N7—C12—C13—C18	3.2 (4)
C2—C3—C4—C9	−178.4 (2)	C11—C12—C13—C18	−179.0 (3)
C1—N1—C5—C4	0.1 (4)	C10—N5—C14—C13	0.5 (4)
C1—N1—C5—S1	−178.62 (19)	C10—N5—C14—S2	−179.4 (2)
C3—C4—C5—N1	−1.6 (4)	C12—C13—C14—N5	−1.2 (4)
C9—C4—C5—N1	178.2 (3)	C18—C13—C14—N5	179.1 (3)
C3—C4—C5—S1	177.2 (2)	C12—C13—C14—S2	178.7 (2)
C9—C4—C5—S1	−3.1 (4)	C18—C13—C14—S2	−1.1 (4)
C6—S1—C5—N1	0.3 (3)	C15—S2—C14—N5	3.4 (3)
C6—S1—C5—C4	−178.5 (2)	C15—S2—C14—C13	−176.4 (2)
C1—N2—C7—O1	6.3 (5)	C10—N6—C16—O2	0.0 (5)
C1—N2—C7—C8	−173.6 (3)	C10—N6—C16—C17	−179.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3AN···O2	0.88	2.00	2.870 (3)	169
N7—H7BN···O1	0.88	1.99	2.860 (3)	170
N3—H3BN···N8ⁱ	0.88	2.33	3.080 (4)	143
N7—H7AN···N4ⁱⁱ	0.88	2.38	3.116 (4)	142
N2—H2N···O3A	0.88	2.12	2.984 (10)	166
N2—H2N···O3B	0.88	2.21	3.079 (9)	172
N6—H6N···O3Aⁱⁱⁱ	0.88	2.26	3.138 (10)	173
N6—H6N···O3Bⁱⁱⁱ	0.88	2.19	3.051 (9)	166
O3A—H3A2···N7^iv	0.85 (2)	2.36 (6)	3.083 (12)	143 (9)
O3B—H3B1···N5^v	0.85 (2)	2.57 (6)	3.239 (8)	137 (8)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3AN···O2	0.88	2.00	2.870 (3)	169
N7—H7BN···O1	0.88	1.99	2.860 (3)	170
N3—H3BN···N8ⁱ	0.88	2.33	3.080 (4)	143
N7—H7AN···N4ⁱⁱ	0.88	2.38	3.116 (4)	142
N2—H2N···O3A	0.88	2.12	2.984 (10)	166
N2—H2N···O3B	0.88	2.21	3.079 (9)	172
N6—H6N···O3Aⁱⁱⁱ	0.88	2.26	3.138 (10)	173
N6—H6N···O3Bⁱⁱⁱ	0.88	2.19	3.051 (9)	166
O3A—H3A2···N7^iv	0.85 (2)	2.36 (6)	3.083 (12)	143 (9)
O3B—H3B1···N5^v	0.85 (2)	2.57 (6)	3.239 (8)	137 (8)

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

Acknowledgements

We are grateful to the University of Tennessee and Sohag University for supporting this study.

References

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Volume 71| Part 3| March 2015| Pages o171-o172

doi:10.1107/S205698901500256X

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

Crystal structure of N-[4-amino-5-cyano-6-(methyl­sulfan­yl)pyridin-2-yl]acetamide hemihydrate

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 N-[4-amino-5-cyano-6-(methylsulfanyl)pyridin-2-yl]acetamide hemihydrate