organic compounds
N-[4-amino-5-cyano-6-(methylsulfanyl)pyridin-2-yl]-2-(cyclohexylsulfanyl)acetamide
ofaDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, bChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, dChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
In the title molecule, C15H20N4OS2, the acetamido fragment is nearly coplanar with the pyridyl ring [C—N—C—C torsion angle = −4.1 (2)°], while the cyclohexylsulfanyl portion protrudes from this plane [N—C—C—S torsion angle = −40.8 (6)°]. In the crystal, alternating pairwise N—H⋯O and N—H⋯N hydrogen bonds across inversion centres form chains along [101], which are associated into stepped layers via offset π–π stacking between pyridyl rings [centroid–centroid distance = 3.566 (1) Å]. The cyclohexyl group and the two atoms of the S—C bond attached to it are disordered over two sets of sites with site-occupancy factors of 0.8845 (18) and 0.1155 (18).
Keywords: crystal structure; acetamido; cyclohexylsulfanyl; hydrogen bonds; π–π stacking.
CCDC reference: 1019463
1. Related literature
For the diverse biological properties of pyridine-containing compounds see: Patrick & Kinsman (1996); Hishmat et al. (1990); Paronikyan et al. (2002); Bernardino et al. (2007); Doshi et al. (1999); Jemmezi et al. (2014); Mamolo et al. (2004); Bhatt et al. (2001). For the structure of a related compound, see: Akkurt et al. (2014).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2013); cell SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 1019463
10.1107/S1600536814018534/bh2502sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814018534/bh2502Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814018534/bh2502Isup3.cml
A mixture of 1 mmol (257 mg) of N-[4-amino-5-cyano-6-(methylthio)pyridin-2-yl]-2-chloroacetamide and 1 mmol (116 mg) of cyclohexanethiol in 30 ml e thanol along with few drops of triethylamine (TEA) as a catalyst was refluxed for 3 h at 350 K. The reaction mixture was allowed to cool down at room temperature and the excess solvent was evaporated under reduced pressure. The resulting solid was filtered off, dried and recrystallized from benzene, to afford colourless crystals (92% yield) suitable for X-ray diffraction. M.p. 463 – 465 K.
IR (νmax, cm-1): 3470, 3325, 3215, (NH2+NH), 2928 (CH aliph.), 2210 (C≡N), 1689 (C=Oamidic); 1H-NMR (DMSO-d6), δ, p.p.m.: 10.27 (s, 1H, NH; exchanged by D2O), 7.30 (s, 1H, CH pyridyl), 6.99 (s, 2H, NH2; exchanged by D2O), 3.41 (s, 2H, COCH2), 2.84–2.82 (m, 1H, CH cyclohexyl), 2.52 (s, 3H, SCH3), 1.95–1.93 (m, 2H, CH2 cyclohexyl), 1.69 (m, 2H, CH2 cyclohexyl), 1.56–1.54 (m, 1H, CH cyclohexyl), 1.28–1.24 (m, 5H, 2CH2+CH cyclohexyl).
H atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å) while those attached to nitrogen were placed in locations derived from a difference map and their parameters adjusted to give N—H = 0.91 Å. All H atoms were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. The cyclohexyl group, S2 and C9 are disordered over two sites [site-occupancy factors are 0.8845 (18) and 0.1155 (18)]. The components of the disorder were refined with restraints that their geometries be the same (Sheldrick, 2008)
Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C15H20N4OS2 | Dx = 1.295 Mg m−3 |
Mr = 336.47 | Melting point: 463 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2269 (8) Å | Cell parameters from 9975 reflections |
b = 24.655 (3) Å | θ = 2.3–29.0° |
c = 9.6933 (11) Å | µ = 0.32 mm−1 |
β = 92.5330 (17)° | T = 150 K |
V = 1725.5 (3) Å3 | Plate, colourless |
Z = 4 | 0.23 × 0.18 × 0.08 mm |
F(000) = 712 |
Bruker SMART APEX CCD diffractometer | 4538 independent reflections |
Radiation source: fine-focus sealed tube | 3713 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 8.3660 pixels mm-1 | θmax = 29.0°, θmin = 2.3° |
ϕ and ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −33→33 |
Tmin = 0.93, Tmax = 0.97 | l = −13→13 |
31462 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)] = 0.040 | Hydrogen site location: mixed |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0492P)2 + 0.7171P] where P = (Fo2 + 2Fc2)/3 |
4538 reflections | (Δ/σ)max = 0.006 |
225 parameters | Δρmax = 0.36 e Å−3 |
68 restraints | Δρmin = −0.26 e Å−3 |
0 constraints |
C15H20N4OS2 | V = 1725.5 (3) Å3 |
Mr = 336.47 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.2269 (8) Å | µ = 0.32 mm−1 |
b = 24.655 (3) Å | T = 150 K |
c = 9.6933 (11) Å | 0.23 × 0.18 × 0.08 mm |
β = 92.5330 (17)° |
Bruker SMART APEX CCD diffractometer | 4538 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | 3713 reflections with I > 2σ(I) |
Tmin = 0.93, Tmax = 0.97 | Rint = 0.047 |
31462 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 68 restraints |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.36 e Å−3 |
4538 reflections | Δρmin = −0.26 e Å−3 |
225 parameters |
Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, collected at ϕ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in ϕ, collected at ω = -30.00 and 210.00°. The scan time was 40 sec/frame. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.12721 (5) | 0.61034 (2) | 0.34743 (4) | 0.03110 (11) | |
O1 | 0.91811 (16) | 0.53918 (5) | 0.71493 (12) | 0.0356 (3) | |
N1 | 0.3292 (2) | 0.54925 (6) | 0.04030 (14) | 0.0378 (3) | |
N2 | 0.41788 (16) | 0.59429 (5) | 0.52327 (12) | 0.0235 (2) | |
N3 | 0.72278 (17) | 0.50958 (5) | 0.23714 (13) | 0.0287 (3) | |
H3A | 0.6773 | 0.4994 | 0.1520 | 0.034* | |
H3B | 0.8363 | 0.4940 | 0.2514 | 0.034* | |
N4 | 0.64424 (17) | 0.58430 (5) | 0.69315 (12) | 0.0264 (3) | |
H4A | 0.5680 | 0.6065 | 0.7397 | 0.032* | |
C1 | 0.35074 (19) | 0.58641 (5) | 0.39522 (15) | 0.0227 (3) | |
C2 | 0.44875 (19) | 0.55937 (5) | 0.29318 (14) | 0.0218 (3) | |
C3 | 0.62544 (18) | 0.53707 (5) | 0.32894 (14) | 0.0222 (3) | |
C4 | 0.69559 (19) | 0.54512 (6) | 0.46531 (14) | 0.0237 (3) | |
H4 | 0.8137 | 0.5314 | 0.4948 | 0.028* | |
C5 | 0.58845 (19) | 0.57337 (6) | 0.55479 (14) | 0.0226 (3) | |
C6 | 0.37713 (19) | 0.55438 (6) | 0.15424 (15) | 0.0258 (3) | |
C7 | 0.0634 (2) | 0.64195 (7) | 0.50548 (17) | 0.0332 (3) | |
H7A | 0.0792 | 0.6160 | 0.5817 | 0.050* | |
H7B | −0.0664 | 0.6535 | 0.4968 | 0.050* | |
H7C | 0.1425 | 0.6736 | 0.5242 | 0.050* | |
C8 | 0.8003 (2) | 0.56755 (6) | 0.76461 (15) | 0.0258 (3) | |
S2 | 0.74307 (10) | 0.65352 (3) | 0.94799 (6) | 0.03506 (15) | 0.8845 (18) |
C9 | 0.8162 (10) | 0.5850 (2) | 0.9147 (11) | 0.0327 (9) | 0.8845 (18) |
H9A | 0.9470 | 0.5811 | 0.9481 | 0.039* | 0.8845 (18) |
H9B | 0.7413 | 0.5600 | 0.9693 | 0.039* | 0.8845 (18) |
C10 | 0.9173 (2) | 0.69109 (7) | 0.85620 (18) | 0.0303 (4) | 0.8845 (18) |
H10 | 0.9378 | 0.6717 | 0.7675 | 0.036* | 0.8845 (18) |
C11 | 0.8422 (3) | 0.74748 (9) | 0.8213 (3) | 0.0504 (6) | 0.8845 (18) |
H11A | 0.8143 | 0.7667 | 0.9075 | 0.061* | 0.8845 (18) |
H11B | 0.7255 | 0.7441 | 0.7645 | 0.061* | 0.8845 (18) |
C12 | 0.9827 (4) | 0.78041 (10) | 0.7421 (3) | 0.0535 (6) | 0.8845 (18) |
H12A | 1.0040 | 0.7625 | 0.6527 | 0.064* | 0.8845 (18) |
H12B | 0.9323 | 0.8171 | 0.7225 | 0.064* | 0.8845 (18) |
C13 | 1.1633 (4) | 0.78515 (11) | 0.8244 (3) | 0.0600 (7) | 0.8845 (18) |
H13A | 1.1437 | 0.8053 | 0.9110 | 0.072* | 0.8845 (18) |
H13B | 1.2532 | 0.8057 | 0.7707 | 0.072* | 0.8845 (18) |
C14 | 1.2412 (3) | 0.72892 (12) | 0.8587 (3) | 0.0629 (7) | 0.8845 (18) |
H14A | 1.3574 | 0.7327 | 0.9159 | 0.075* | 0.8845 (18) |
H14B | 1.2708 | 0.7102 | 0.7721 | 0.075* | 0.8845 (18) |
C15 | 1.1027 (3) | 0.69463 (11) | 0.9368 (3) | 0.0555 (6) | 0.8845 (18) |
H15A | 1.1534 | 0.6577 | 0.9517 | 0.067* | 0.8845 (18) |
H15B | 1.0842 | 0.7111 | 1.0284 | 0.067* | 0.8845 (18) |
S2A | 0.6907 (8) | 0.6447 (2) | 0.9744 (5) | 0.03506 (15) | 0.1155 (18) |
C9A | 0.833 (9) | 0.589 (2) | 0.918 (9) | 0.0327 (9) | 0.1155 (18) |
H9A1 | 0.9638 | 0.6007 | 0.9302 | 0.039* | 0.1155 (18) |
H9A2 | 0.8151 | 0.5584 | 0.9817 | 0.039* | 0.1155 (18) |
C10A | 0.8290 (17) | 0.7034 (5) | 0.9292 (12) | 0.0303 (4) | 0.1155 (18) |
H10A | 0.7526 | 0.7352 | 0.9560 | 0.036* | 0.1155 (18) |
C11A | 0.854 (3) | 0.7113 (6) | 0.7781 (15) | 0.0504 (6) | 0.1155 (18) |
H11C | 0.7317 | 0.7120 | 0.7283 | 0.061* | 0.1155 (18) |
H11D | 0.9259 | 0.6806 | 0.7420 | 0.061* | 0.1155 (18) |
C12A | 0.955 (3) | 0.7639 (8) | 0.753 (3) | 0.0535 (6) | 0.1155 (18) |
H12C | 0.8818 | 0.7945 | 0.7879 | 0.064* | 0.1155 (18) |
H12D | 0.9664 | 0.7690 | 0.6524 | 0.064* | 0.1155 (18) |
C13A | 1.148 (3) | 0.7645 (10) | 0.8242 (19) | 0.0600 (7) | 0.1155 (18) |
H13C | 1.2163 | 0.7980 | 0.8013 | 0.072* | 0.1155 (18) |
H13D | 1.2214 | 0.7326 | 0.7971 | 0.072* | 0.1155 (18) |
C14A | 1.109 (2) | 0.7627 (8) | 0.9781 (18) | 0.0629 (7) | 0.1155 (18) |
H14C | 1.2265 | 0.7651 | 1.0337 | 0.075* | 0.1155 (18) |
H14D | 1.0308 | 0.7941 | 1.0018 | 0.075* | 0.1155 (18) |
C15A | 1.009 (2) | 0.7104 (8) | 1.013 (2) | 0.0555 (6) | 0.1155 (18) |
H15C | 1.0912 | 0.6792 | 0.9947 | 0.067* | 0.1155 (18) |
H15D | 0.9836 | 0.7102 | 1.1120 | 0.067* | 0.1155 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02353 (18) | 0.0410 (2) | 0.0283 (2) | 0.00880 (15) | −0.00329 (14) | −0.00609 (15) |
O1 | 0.0297 (6) | 0.0485 (7) | 0.0281 (6) | 0.0102 (5) | −0.0041 (4) | −0.0026 (5) |
N1 | 0.0409 (8) | 0.0456 (8) | 0.0261 (7) | 0.0097 (6) | −0.0061 (6) | −0.0053 (6) |
N2 | 0.0222 (6) | 0.0265 (6) | 0.0217 (6) | 0.0017 (4) | −0.0002 (4) | −0.0023 (5) |
N3 | 0.0253 (6) | 0.0402 (7) | 0.0206 (6) | 0.0068 (5) | −0.0003 (5) | −0.0054 (5) |
N4 | 0.0270 (6) | 0.0320 (6) | 0.0201 (6) | 0.0037 (5) | −0.0010 (5) | −0.0048 (5) |
C1 | 0.0201 (6) | 0.0235 (6) | 0.0245 (7) | −0.0005 (5) | 0.0002 (5) | −0.0004 (5) |
C2 | 0.0222 (6) | 0.0233 (6) | 0.0199 (6) | 0.0000 (5) | −0.0004 (5) | −0.0003 (5) |
C3 | 0.0216 (6) | 0.0239 (6) | 0.0212 (6) | −0.0013 (5) | 0.0023 (5) | 0.0002 (5) |
C4 | 0.0195 (6) | 0.0288 (7) | 0.0226 (7) | 0.0012 (5) | −0.0007 (5) | −0.0013 (5) |
C5 | 0.0225 (6) | 0.0248 (6) | 0.0204 (6) | −0.0018 (5) | −0.0012 (5) | −0.0007 (5) |
C6 | 0.0242 (7) | 0.0277 (7) | 0.0253 (7) | 0.0043 (5) | −0.0006 (5) | −0.0019 (5) |
C7 | 0.0285 (7) | 0.0363 (8) | 0.0353 (8) | 0.0062 (6) | 0.0058 (6) | −0.0048 (7) |
C8 | 0.0280 (7) | 0.0270 (7) | 0.0221 (7) | −0.0040 (5) | −0.0021 (5) | 0.0018 (5) |
S2 | 0.0358 (3) | 0.0437 (3) | 0.0258 (3) | 0.0014 (2) | 0.0031 (2) | −0.0104 (2) |
C9 | 0.0430 (19) | 0.0336 (14) | 0.0210 (10) | −0.0013 (13) | −0.0052 (14) | 0.0001 (11) |
C10 | 0.0315 (9) | 0.0308 (8) | 0.0283 (9) | 0.0031 (7) | −0.0019 (7) | −0.0059 (7) |
C11 | 0.0486 (12) | 0.0362 (10) | 0.0669 (15) | 0.0101 (9) | 0.0078 (11) | −0.0019 (10) |
C12 | 0.0639 (16) | 0.0350 (14) | 0.0615 (15) | 0.0021 (12) | 0.0024 (12) | 0.0057 (13) |
C13 | 0.0766 (17) | 0.0525 (16) | 0.0504 (13) | −0.0250 (15) | −0.0012 (12) | −0.0093 (13) |
C14 | 0.0373 (12) | 0.0873 (19) | 0.0622 (16) | −0.0158 (12) | −0.0173 (11) | 0.0164 (14) |
C15 | 0.0405 (12) | 0.0721 (16) | 0.0521 (14) | −0.0090 (11) | −0.0170 (10) | 0.0152 (12) |
S2A | 0.0358 (3) | 0.0437 (3) | 0.0258 (3) | 0.0014 (2) | 0.0031 (2) | −0.0104 (2) |
C9A | 0.0430 (19) | 0.0336 (14) | 0.0210 (10) | −0.0013 (13) | −0.0052 (14) | 0.0001 (11) |
C10A | 0.0315 (9) | 0.0308 (8) | 0.0283 (9) | 0.0031 (7) | −0.0019 (7) | −0.0059 (7) |
C11A | 0.0486 (12) | 0.0362 (10) | 0.0669 (15) | 0.0101 (9) | 0.0078 (11) | −0.0019 (10) |
C12A | 0.0639 (16) | 0.0350 (14) | 0.0615 (15) | 0.0021 (12) | 0.0024 (12) | 0.0057 (13) |
C13A | 0.0766 (17) | 0.0525 (16) | 0.0504 (13) | −0.0250 (15) | −0.0012 (12) | −0.0093 (13) |
C14A | 0.0373 (12) | 0.0873 (19) | 0.0622 (16) | −0.0158 (12) | −0.0173 (11) | 0.0164 (14) |
C15A | 0.0405 (12) | 0.0721 (16) | 0.0521 (14) | −0.0090 (11) | −0.0170 (10) | 0.0152 (12) |
S1—C1 | 1.7624 (14) | C12—C13 | 1.505 (4) |
S1—C7 | 1.7972 (16) | C12—H12A | 0.9900 |
O1—C8 | 1.2173 (18) | C12—H12B | 0.9900 |
N1—C6 | 1.150 (2) | C13—C14 | 1.527 (4) |
N2—C1 | 1.3269 (18) | C13—H13A | 0.9900 |
N2—C5 | 1.3586 (18) | C13—H13B | 0.9900 |
N3—C3 | 1.3422 (18) | C14—C15 | 1.535 (3) |
N3—H3A | 0.9101 | C14—H14A | 0.9900 |
N3—H3B | 0.9104 | C14—H14B | 0.9900 |
N4—C8 | 1.3616 (19) | C15—H15A | 0.9900 |
N4—C5 | 1.4093 (18) | C15—H15B | 0.9900 |
N4—H4A | 0.9098 | S2A—C9A | 1.807 (18) |
C1—C2 | 1.4094 (19) | S2A—C10A | 1.823 (12) |
C2—C3 | 1.4190 (19) | C9A—H9A1 | 0.9900 |
C2—C6 | 1.427 (2) | C9A—H9A2 | 0.9900 |
C3—C4 | 1.4087 (19) | C10A—C11A | 1.496 (13) |
C4—C5 | 1.3770 (19) | C10A—C15A | 1.511 (12) |
C4—H4 | 0.9500 | C10A—H10A | 1.0000 |
C7—H7A | 0.9800 | C11A—C12A | 1.512 (13) |
C7—H7B | 0.9800 | C11A—H11C | 0.9900 |
C7—H7C | 0.9800 | C11A—H11D | 0.9900 |
C8—C9 | 1.516 (10) | C12A—C13A | 1.529 (14) |
C8—C9A | 1.59 (8) | C12A—H12C | 0.9900 |
S2—C9 | 1.803 (4) | C12A—H12D | 0.9900 |
S2—C10 | 1.826 (2) | C13A—C14A | 1.533 (14) |
C9—H9A | 0.9900 | C13A—H13C | 0.9900 |
C9—H9B | 0.9900 | C13A—H13D | 0.9900 |
C10—C15 | 1.523 (3) | C14A—C15A | 1.520 (13) |
C10—C11 | 1.525 (3) | C14A—H14C | 0.9900 |
C10—H10 | 1.0000 | C14A—H14D | 0.9900 |
C11—C12 | 1.532 (4) | C15A—H15C | 0.9900 |
C11—H11A | 0.9900 | C15A—H15D | 0.9900 |
C11—H11B | 0.9900 | ||
C1—S1—C7 | 100.83 (7) | C12—C13—H13A | 109.6 |
C1—N2—C5 | 116.45 (12) | C14—C13—H13A | 109.6 |
C3—N3—H3A | 124.2 | C12—C13—H13B | 109.6 |
C3—N3—H3B | 127.4 | C14—C13—H13B | 109.6 |
H3A—N3—H3B | 107.9 | H13A—C13—H13B | 108.1 |
C8—N4—C5 | 128.45 (12) | C13—C14—C15 | 111.4 (2) |
C8—N4—H4A | 115.9 | C13—C14—H14A | 109.3 |
C5—N4—H4A | 115.6 | C15—C14—H14A | 109.3 |
N2—C1—C2 | 123.46 (13) | C13—C14—H14B | 109.3 |
N2—C1—S1 | 119.33 (10) | C15—C14—H14B | 109.3 |
C2—C1—S1 | 117.21 (11) | H14A—C14—H14B | 108.0 |
C1—C2—C3 | 119.11 (12) | C10—C15—C14 | 110.86 (18) |
C1—C2—C6 | 122.05 (12) | C10—C15—H15A | 109.5 |
C3—C2—C6 | 118.83 (12) | C14—C15—H15A | 109.5 |
N3—C3—C4 | 121.05 (13) | C10—C15—H15B | 109.5 |
N3—C3—C2 | 121.74 (13) | C14—C15—H15B | 109.5 |
C4—C3—C2 | 117.21 (12) | H15A—C15—H15B | 108.1 |
C5—C4—C3 | 118.24 (13) | C9A—S2A—C10A | 102 (3) |
C5—C4—H4 | 120.9 | C8—C9A—S2A | 118 (4) |
C3—C4—H4 | 120.9 | C8—C9A—H9A1 | 107.7 |
N2—C5—C4 | 125.47 (13) | S2A—C9A—H9A1 | 107.7 |
N2—C5—N4 | 111.10 (12) | C8—C9A—H9A2 | 107.7 |
C4—C5—N4 | 123.44 (13) | S2A—C9A—H9A2 | 107.7 |
N1—C6—C2 | 176.06 (16) | H9A1—C9A—H9A2 | 107.1 |
S1—C7—H7A | 109.5 | C11A—C10A—C15A | 111.7 (13) |
S1—C7—H7B | 109.5 | C11A—C10A—S2A | 115.5 (9) |
H7A—C7—H7B | 109.5 | C15A—C10A—S2A | 115.5 (9) |
S1—C7—H7C | 109.5 | C11A—C10A—H10A | 104.2 |
H7A—C7—H7C | 109.5 | C15A—C10A—H10A | 104.2 |
H7B—C7—H7C | 109.5 | S2A—C10A—H10A | 104.2 |
O1—C8—N4 | 123.44 (14) | C10A—C11A—C12A | 110.5 (17) |
O1—C8—C9 | 121.2 (3) | C10A—C11A—H11C | 109.6 |
N4—C8—C9 | 115.3 (3) | C12A—C11A—H11C | 109.6 |
O1—C8—C9A | 119.2 (18) | C10A—C11A—H11D | 109.6 |
N4—C8—C9A | 117.3 (17) | C12A—C11A—H11D | 109.6 |
C9—S2—C10 | 100.0 (3) | H11C—C11A—H11D | 108.1 |
C8—C9—S2 | 115.3 (6) | C11A—C12A—C13A | 111.9 (17) |
C8—C9—H9A | 108.4 | C11A—C12A—H12C | 109.2 |
S2—C9—H9A | 108.4 | C13A—C12A—H12C | 109.2 |
C8—C9—H9B | 108.4 | C11A—C12A—H12D | 109.2 |
S2—C9—H9B | 108.4 | C13A—C12A—H12D | 109.2 |
H9A—C9—H9B | 107.5 | H12C—C12A—H12D | 107.9 |
C15—C10—C11 | 110.98 (18) | C12A—C13A—C14A | 103 (2) |
C15—C10—S2 | 112.88 (14) | C12A—C13A—H13C | 111.1 |
C11—C10—S2 | 108.92 (14) | C14A—C13A—H13C | 111.1 |
C15—C10—H10 | 108.0 | C12A—C13A—H13D | 111.1 |
C11—C10—H10 | 108.0 | C14A—C13A—H13D | 111.1 |
S2—C10—H10 | 108.0 | H13C—C13A—H13D | 109.0 |
C10—C11—C12 | 110.92 (19) | C15A—C14A—C13A | 110.5 (17) |
C10—C11—H11A | 109.5 | C15A—C14A—H14C | 109.6 |
C12—C11—H11A | 109.5 | C13A—C14A—H14C | 109.6 |
C10—C11—H11B | 109.5 | C15A—C14A—H14D | 109.6 |
C12—C11—H11B | 109.5 | C13A—C14A—H14D | 109.6 |
H11A—C11—H11B | 108.0 | H14C—C14A—H14D | 108.1 |
C13—C12—C11 | 110.7 (2) | C10A—C15A—C14A | 112.5 (13) |
C13—C12—H12A | 109.5 | C10A—C15A—H15C | 109.1 |
C11—C12—H12A | 109.5 | C14A—C15A—H15C | 109.1 |
C13—C12—H12B | 109.5 | C10A—C15A—H15D | 109.1 |
C11—C12—H12B | 109.5 | C14A—C15A—H15D | 109.1 |
H12A—C12—H12B | 108.1 | H15C—C15A—H15D | 107.8 |
C12—C13—C14 | 110.3 (2) | ||
C5—N2—C1—C2 | −1.8 (2) | C10—S2—C9—C8 | −65.2 (5) |
C5—N2—C1—S1 | 177.97 (10) | C9—S2—C10—C15 | −78.6 (4) |
C7—S1—C1—N2 | 1.40 (13) | C9—S2—C10—C11 | 157.7 (4) |
C7—S1—C1—C2 | −178.84 (11) | C15—C10—C11—C12 | 56.0 (3) |
N2—C1—C2—C3 | 2.8 (2) | S2—C10—C11—C12 | −179.18 (18) |
S1—C1—C2—C3 | −176.92 (10) | C10—C11—C12—C13 | −57.8 (3) |
N2—C1—C2—C6 | −176.20 (13) | C11—C12—C13—C14 | 57.8 (3) |
S1—C1—C2—C6 | 4.05 (18) | C12—C13—C14—C15 | −56.8 (3) |
C1—C2—C3—N3 | 178.10 (13) | C11—C10—C15—C14 | −54.6 (3) |
C6—C2—C3—N3 | −2.8 (2) | S2—C10—C15—C14 | −177.19 (19) |
C1—C2—C3—C4 | −2.14 (19) | C13—C14—C15—C10 | 55.2 (3) |
C6—C2—C3—C4 | 176.93 (13) | O1—C8—C9A—S2A | 164 (3) |
N3—C3—C4—C5 | −179.59 (13) | N4—C8—C9A—S2A | −13 (6) |
C2—C3—C4—C5 | 0.6 (2) | C10A—S2A—C9A—C8 | −90 (5) |
C1—N2—C5—C4 | 0.1 (2) | C9A—S2A—C10A—C11A | 65 (3) |
C1—N2—C5—N4 | −179.93 (12) | C9A—S2A—C10A—C15A | −68 (3) |
C3—C4—C5—N2 | 0.4 (2) | C15A—C10A—C11A—C12A | −51 (2) |
C3—C4—C5—N4 | −179.53 (13) | S2A—C10A—C11A—C12A | 174.6 (14) |
C8—N4—C5—N2 | 176.01 (14) | C10A—C11A—C12A—C13A | 61 (3) |
C8—N4—C5—C4 | −4.1 (2) | C11A—C12A—C13A—C14A | −65 (3) |
C5—N4—C8—O1 | −0.2 (2) | C12A—C13A—C14A—C15A | 62 (2) |
C5—N4—C8—C9 | −178.1 (4) | C11A—C10A—C15A—C14A | 51 (2) |
C5—N4—C8—C9A | 176 (3) | S2A—C10A—C15A—C14A | −174.9 (14) |
O1—C8—C9—S2 | 141.3 (3) | C13A—C14A—C15A—C10A | −58 (2) |
N4—C8—C9—S2 | −40.8 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O1i | 0.91 | 1.97 | 2.8792 (17) | 179 |
N3—H3A···N1ii | 0.91 | 2.22 | 3.0640 (19) | 155 |
C4—H4···O1 | 0.95 | 2.24 | 2.8493 (18) | 121 |
C7—H7A···O1iii | 0.98 | 2.60 | 3.440 (2) | 144 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O1i | 0.91 | 1.97 | 2.8792 (17) | 179 |
N3—H3A···N1ii | 0.91 | 2.22 | 3.0640 (19) | 155 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z. |
Footnotes
‡Other affiliation: Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt.
Acknowledgements
JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
A large number of heterocyclic compounds containing pyridine rings are associated with diverse pharmacological properties such as antifungal (Patrick & Kinsman, 1996; Hishmat et al., 1990), anticancer, anticonvulsant (Paronikyan et al., 2002), antiviral (Bernardino et al., 2007), antibacterial, antimicrobial (Doshi et al., 1999; Jemmezi et al., 2014), antimycobacterial (Mamolo et al., 2004) and insecticidal activities (Bhatt et al., 2001). In this connection, and as part of our on-going study on synthesis of bio-active heterocyclic molecules, we herein report the synthesis and crystal determination of the title compound.
In the title molecule (Fig. 1), the acetamido fragment is nearly coplanar with the pyridyl ring [C8—N4—C5—C4 torsion angle = -4.1 (2)°], possibly aided by a weak C4—H4···O1 interaction (Table 1), while the cyclohexylsulfanyl portion protrudes from this plane [N4—C8—C9—S2 torsion angle = -40.8 (6)°]. The main disordered part of the cyclohexyl group adopts the chair conformation with puckering parameters Q = 0.578 (3) Å, θ = 177.6 (3)°, and ϕ = 311 (3)°. The minor disordered part of the cyclohexyl group exhibits a distorted chair conformation with puckering parameters Q = 0.60 (2) Å, θ = 11.3 (19) °, and ϕ = 173 (10) °. All the bond lengths and bond angles are normal and comparable with those reported for a related compound (Akkurt et al., 2014).
Alternating, pairwise N3—H3B···O1 and N3—H3A···N1 hydrogen bonds across centres of symmetry form chains (Fig. 2 and Table 1) which are associated into stepped layers via offset π-stacking between pyridyl rings [Fig. 3; interplanar distance = 3.384 (1) Å; Cg···Cgi = 3.566 (1) Å, where Cg is the centroid of the C1···C5/N2 ring; i: 1 - x, 1 - y, 1 - z]. Adjacent stacks are inclined to one another by approximately 62°.