organic compounds
(E)-2-Phenyl-N-(thiophen-2-ylmethylidene)imidazo[1,2-a]pyridin-3-amine
aLaboratoire de Chimie Appliquée et Environnement (LCAE), Faculté des Sciences, Université Mohammed Premier, BP 524, 60000 Oujda, Morocco, and bLaboratoire de Chimie du Solide Appliquée, Faculty of Sciences, Mohammed V University in Rabat, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: a_elaatiaoui@yahoo.fr
The 18H13N3S, is build up from two independent molecules slightly inclined to each other. In each molecule, the imidazo[1,2-a]pyridine ring system is almost planar, with the largest deviation from the mean plane being 0.022 (1) Å in the first molecule and 0.018 (1) Å in the second molecule. The fused-ring system belonging to the first molecule makes dihedral angles of 24.06 (7) and 40.52 (8)° with the thiophenyl and phenyl rings, respectively. The corresponding values observed in the second molecule are nearly the same, namely 25.20 (7) and 38.99 (7)°, respectively. The dihedral angle between the thiophenyl and phenyl rings is 63.47 (9)° in the first molecule and 47.49 (9)° in the second. The cohesion of the is ensured by two C—H⋯N hydrogen bonds between molecules and by three C—H⋯π interactions, forming a three-dimensional network.
of the title compound, CKeywords: crystal structure; phenylimidazo[1,2-a]pyridine; thiophenyl; hydrogen bonds; C—H⋯π interactions.
CCDC reference: 1477135
Structure description
et al., 2002), antibacterial and antifungal activities (Shi et al., 2007), anticonvulsant (Sridhar et al., 2002; Kaplan et al., 1980), antituberculosis (Patole et al., 2006; Hearn & Cynamon, 2004), analgesic and anti-inflammatory properties (Bhandari et al., 2008). The present paper is a continuation of our research work devoted to the development of imidazo[1,2-a]pyridine derivatives with potential pharmacological activities (Elaatiaoui et al., 2014, 2015).
bearing an azomethine –C=N–, have gained importance in the pharmaceutical and medicinal industries due to their widespread potential biological activities such as anticancer (RenThe heterobicyclic ring system in the title compound is essentially planar, with a maximum deviation of 0.022 (1) Å for atom C6 in the first molecule (S1/N1–N3/C1–C18) and 0.018 (1) Å for atom N5 in the second molecule (S2/N4–N6/C19–C36) (Fig. 1). In the first molecule, the dihedral angles between the mean plane through the fused-ring system (N2/N3/C6–C12) and the thiophen-2-yl (S1/C1–C4) and phenyl (C13–C18) rings are of 24.06 (7) and 40.52 (8)°, respectively. Nearly the same values are observed in the second molecule between the imidazo[1,2-a]pyridin system and the thiophen-2-yl (S2/C19–C22) and the phenyl (C31–C36) rings, viz. 25.20 (7) and 38.99 (7)°, respectively. The dihedral angle between the thiophen-2-yl and phenyl rings is 63.47 (9)° in the first molecule and 47.49 (9)° in the second. A least-squares fit of the two molecules is shown in Fig. 2.
In the crystal, molecules are linked together by two C—H⋯N hydrogen bonds between the molecules and by C—H⋯π interactions, forming a three dimensional network (Fig. 3 and Table 1).
Synthesis and crystallization
A solution of 2-phenylimidazo[1,2-a]pyridin-3-amine (0.5 g, 2.39 mmol) and thiophene-2-carbaldehyde (0.27 g, 2.39 mmol) in 20 ml of dry diethyl ether was stirred at room temperature for 24 h using a 0.3 ml of acetic acid as catalyst. The solvent was evaporated. The resulting solid purified by (CH2Cl2/MeOH 99/1) and crystallized from methanol to give the final yellow product (yield 86.15%, m.p. = 399 K).
Spectroscopic data: (E)-N-(2-phenylimidazo[1,2-a]pyridin-3-yl)-1-(thiophen-2-yl)methanimine. Rf = 0.55 (silica, CH2Cl2/MeOH, 9/1). 1H NMR (300 MHz, DMSO, δ (p.p.m.): 9.22 (s, 1H, C17H=N); 8.61 (d, 1H, C3H, J = 6.24 Hz); 8.00 (d, 2H, C11H, C15H, J = 7.26 Hz); 7.90 (d, 1H, C6H, J = 4.95); 7.49 (t, 8H, C1H, C2H, C12H, C13H, C14H, C20H, C21H, C22H); m/z (M+1): 304. IR (KBr): ν(CH=N, imine) = 1560 cm−1.
Refinement
Crystal data, data collection and structure . The reflections (0 1 1) and (0 0 1) affected by the beam-stop were removed during refinement.
details are summarized in Table 2
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Structural data
CCDC reference: 1477135
10.1107/S2414314616007239/bt4007sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616007239/bt4007Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616007239/bt4007Isup3.cml
A solution of 2-phenylimidazo[1,2-a]pyridin-3-amine (0.5 g, 2.39 mmol) and thiophene-2-carbaldehyde (0.27 g, 2.39 mmol) in 20 ml of dry diethyl ether was stirred at room temperature for 24 h using a 0.3 ml of acetic acid as catalyst. The solvent was evaporated. The resulting solid purified by
(CH2Cl2/MeOH 99/1) and crystallized from methanol to give the final yellow–pink product (yield 86.15%, m.p. = 399 K).Spectroscopic data of representative compound: (E)-N-(2-phenylimidazo[1,2-a]pyridin-3-yl)-1-(thiophen-2-yl)methanimine. Rf = 0.55 (silica, CH2Cl2/MeOH, 9/1). 1H NMR (300 MHz, DMSO, δ (p.p.m.): 9.22 (s, 1H, C17H═N); 8.61 (d, 1H, C3H, J = 6.24 Hz); 8.00 (d, 2H, C11H, C15H, J = 7.26 Hz); 7.90 (d, 1H, C6H, J = 4.95); 7.49 (t, 8H, C1H, C2H, C12H, C13H, C14H, C20H, C21H, C22H); m/z (M+1): 304. IR (KBr): ν(CH═N, imine) = 1560 cm-1.
Crystal data, data collection and structure
details are summarized in Table 2. The reflections (0 1 1) and (0 0 1) affected by the beam-stop were removed during refinement.Schiff bases bearing an azomethine ═N–, have gained importance in the pharmaceutical and medicinal industries due to their widespread potential biological activities such as anticancer (Ren et al., 2002), antibacterial and antifungal activities (Shi et al., 2007), anticonvulsant (Sridhar et al., 2002; Kaplan et al., 1980), antituberculosis (Patole et al., 2006; Hearn & Cynamon, 2004), analgesic and anti-inflammatory properties (Bhandari et al., 2008). The present paper is a continuation of our research work devoted to the development of imidazo[1,2-a]pyridine derivatives with potential pharmacological activities (Elaatiaoui et al., 2014, 2015).
–CThe heterobicyclic ring system in the title compound is essentially planar, with a maximum deviation of 0.022 (1) Å for atom C6 in the first molecule (S1/N1–N3/C1–C18) and 0.018 (1) Å for atom N5 in the second molecule (S2/N4–N6/C19–C36) (Fig. 1). In the first molecule, the dihedral angles between the mean plane through the fused-ring system (N2/N3/C6–C12) and the thiophen-2-yl (S1/C1–C4) and phenyl (C13–C18) rings are of 24.06 (7) and 40.52 (8)°, respectively. Nearly the same values are observed in the second molecule between the imidazo[1,2-a]pyridin system and the thiophen-2-yl (S2/C19–C22) and the phenyl (C31–C36) rings, viz. 25.20 (7) and 38.99 (7)°, respectively. The dihedral angle between the thiophen-2-yl and phenyl rings is 63.47 (9)° in the first molecule and 47.49 (9)° in the second. A least-squares fit of the two molecules is shown in Fig. 2.
In the crystal, molecules are linked together by two C—H···N hydrogen bonds between the molecules and by C—H···π interactions, forming a three dimensional network (Fig. 3 and Table 1).
Data collection: APEX2 (Bruker, 2009); cell
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: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).Fig. 1. Plot of the molecule of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles. | |
Fig. 2. Least-squares fit of the two molecules in the asymmetric unit (one molecule inverted); the r.m.s. deviation for all non-H atoms is 0.263 Å. | |
Fig. 3. Three-dimensional plot of the title compound showing molecules linked by hydrogen bonds (dashed blue lines) and C—H···π interaction (dashed green lines). |
C18H13N3S | Z = 4 |
Mr = 303.37 | F(000) = 632 |
Triclinic, P1 | Dx = 1.332 Mg m−3 |
a = 9.6524 (17) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.1168 (17) Å | Cell parameters from 8471 reflections |
c = 16.655 (3) Å | θ = 2.1–29.6° |
α = 101.299 (8)° | µ = 0.21 mm−1 |
β = 106.315 (9)° | T = 296 K |
γ = 95.628 (8)° | Parallelepiped, yellow |
V = 1510.3 (5) Å3 | 0.44 × 0.21 × 0.12 mm |
Bruker X8 APEX diffractometer | 8471 independent reflections |
Radiation source: fine-focus sealed tube | 5839 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
φ and ω scans | θmax = 29.6°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −13→13 |
Tmin = 0.641, Tmax = 0.746 | k = −14→14 |
66495 measured reflections | l = −23→23 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0559P)2 + 0.3505P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
8471 reflections | Δρmax = 0.29 e Å−3 |
397 parameters | Δρmin = −0.48 e Å−3 |
C18H13N3S | γ = 95.628 (8)° |
Mr = 303.37 | V = 1510.3 (5) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.6524 (17) Å | Mo Kα radiation |
b = 10.1168 (17) Å | µ = 0.21 mm−1 |
c = 16.655 (3) Å | T = 296 K |
α = 101.299 (8)° | 0.44 × 0.21 × 0.12 mm |
β = 106.315 (9)° |
Bruker X8 APEX diffractometer | 8471 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 5839 reflections with I > 2σ(I) |
Tmin = 0.641, Tmax = 0.746 | Rint = 0.042 |
66495 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.29 e Å−3 |
8471 reflections | Δρmin = −0.48 e Å−3 |
397 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.17058 (19) | 1.07411 (19) | 0.26058 (13) | 0.0566 (5) | |
H1 | 0.0964 | 1.1046 | 0.2811 | 0.068* | |
C2 | 0.17571 (19) | 1.07047 (19) | 0.18053 (12) | 0.0553 (4) | |
H2 | 0.1049 | 1.0979 | 0.1392 | 0.066* | |
C3 | 0.29993 (18) | 1.02058 (17) | 0.16562 (11) | 0.0450 (4) | |
H3 | 0.3202 | 1.0120 | 0.1136 | 0.054* | |
C4 | 0.38753 (16) | 0.98610 (14) | 0.23621 (9) | 0.0358 (3) | |
C5 | 0.51463 (16) | 0.92090 (15) | 0.24091 (10) | 0.0394 (3) | |
H5 | 0.5508 | 0.9077 | 0.1943 | 0.047* | |
C6 | 0.68652 (15) | 0.80001 (14) | 0.31175 (9) | 0.0351 (3) | |
C7 | 0.67572 (17) | 0.76611 (17) | 0.45524 (10) | 0.0438 (4) | |
H7 | 0.6157 | 0.8308 | 0.4630 | 0.053* | |
C8 | 0.72008 (18) | 0.69263 (18) | 0.51458 (10) | 0.0487 (4) | |
H8 | 0.6906 | 0.7071 | 0.5637 | 0.058* | |
C9 | 0.81108 (18) | 0.59378 (17) | 0.50265 (10) | 0.0465 (4) | |
H9 | 0.8398 | 0.5431 | 0.5436 | 0.056* | |
C10 | 0.85662 (16) | 0.57250 (16) | 0.43193 (10) | 0.0420 (3) | |
H10 | 0.9171 | 0.5080 | 0.4245 | 0.050* | |
C11 | 0.81172 (15) | 0.64882 (15) | 0.36971 (9) | 0.0355 (3) | |
C12 | 0.76267 (15) | 0.73725 (14) | 0.25917 (9) | 0.0349 (3) | |
C13 | 0.76897 (16) | 0.75279 (15) | 0.17423 (9) | 0.0371 (3) | |
C14 | 0.78455 (18) | 0.87931 (16) | 0.15375 (11) | 0.0445 (4) | |
H14 | 0.7897 | 0.9584 | 0.1946 | 0.053* | |
C15 | 0.7924 (2) | 0.88867 (19) | 0.07363 (12) | 0.0545 (4) | |
H15 | 0.8021 | 0.9738 | 0.0607 | 0.065* | |
C16 | 0.7860 (2) | 0.7727 (2) | 0.01279 (12) | 0.0618 (5) | |
H16 | 0.7900 | 0.7791 | −0.0415 | 0.074* | |
C17 | 0.7738 (3) | 0.6472 (2) | 0.03267 (12) | 0.0695 (6) | |
H17 | 0.7713 | 0.5688 | −0.0080 | 0.083* | |
C18 | 0.7651 (2) | 0.63667 (18) | 0.11265 (11) | 0.0551 (5) | |
H18 | 0.7565 | 0.5513 | 0.1254 | 0.066* | |
C19 | 0.15325 (19) | 0.58262 (18) | 0.24891 (12) | 0.0537 (4) | |
H19 | 0.0670 | 0.6036 | 0.2590 | 0.064* | |
C20 | 0.21283 (19) | 0.63493 (17) | 0.19618 (11) | 0.0504 (4) | |
H20 | 0.1724 | 0.6964 | 0.1653 | 0.060* | |
C21 | 0.34351 (18) | 0.58659 (17) | 0.19260 (11) | 0.0469 (4) | |
H21 | 0.3987 | 0.6131 | 0.1591 | 0.056* | |
C22 | 0.38076 (16) | 0.49675 (15) | 0.24342 (9) | 0.0358 (3) | |
C23 | 0.50661 (16) | 0.42895 (15) | 0.25537 (10) | 0.0387 (3) | |
H23 | 0.5732 | 0.4454 | 0.2261 | 0.046* | |
C24 | 0.65015 (15) | 0.28079 (14) | 0.31498 (9) | 0.0354 (3) | |
C25 | 0.64809 (18) | 0.25257 (17) | 0.46057 (10) | 0.0463 (4) | |
H25 | 0.5669 | 0.2949 | 0.4610 | 0.056* | |
C26 | 0.7178 (2) | 0.20410 (19) | 0.52865 (11) | 0.0528 (4) | |
H26 | 0.6829 | 0.2111 | 0.5758 | 0.063* | |
C27 | 0.8433 (2) | 0.14293 (19) | 0.52856 (12) | 0.0547 (4) | |
H27 | 0.8905 | 0.1103 | 0.5758 | 0.066* | |
C28 | 0.89535 (18) | 0.13129 (17) | 0.46045 (11) | 0.0492 (4) | |
H28 | 0.9784 | 0.0916 | 0.4610 | 0.059* | |
C29 | 0.82264 (16) | 0.17983 (15) | 0.38854 (10) | 0.0383 (3) | |
C30 | 0.74535 (15) | 0.24182 (14) | 0.26932 (9) | 0.0357 (3) | |
C31 | 0.74357 (16) | 0.25291 (15) | 0.18214 (10) | 0.0376 (3) | |
C32 | 0.61448 (19) | 0.22930 (18) | 0.11395 (10) | 0.0498 (4) | |
H32 | 0.5251 | 0.2085 | 0.1233 | 0.060* | |
C33 | 0.6181 (2) | 0.2365 (2) | 0.03260 (11) | 0.0607 (5) | |
H33 | 0.5312 | 0.2206 | −0.0124 | 0.073* | |
C34 | 0.7490 (2) | 0.26692 (19) | 0.01772 (12) | 0.0608 (5) | |
H34 | 0.7510 | 0.2719 | −0.0371 | 0.073* | |
C35 | 0.8771 (2) | 0.28999 (19) | 0.08419 (13) | 0.0578 (5) | |
H35 | 0.9659 | 0.3111 | 0.0743 | 0.069* | |
C36 | 0.87527 (18) | 0.28216 (17) | 0.16590 (11) | 0.0480 (4) | |
H36 | 0.9629 | 0.2966 | 0.2103 | 0.058* | |
N1 | 0.57877 (13) | 0.88081 (12) | 0.30812 (8) | 0.0384 (3) | |
N2 | 0.72080 (12) | 0.74350 (12) | 0.38341 (7) | 0.0349 (3) | |
N3 | 0.83822 (13) | 0.64448 (13) | 0.29550 (8) | 0.0385 (3) | |
N4 | 0.52949 (13) | 0.34609 (13) | 0.30544 (8) | 0.0389 (3) | |
N5 | 0.69919 (13) | 0.23822 (12) | 0.39100 (8) | 0.0358 (3) | |
N6 | 0.85190 (14) | 0.18142 (13) | 0.31564 (8) | 0.0416 (3) | |
S1 | 0.31655 (5) | 1.01616 (5) | 0.32036 (3) | 0.04986 (13) | |
S2 | 0.25440 (5) | 0.47252 (5) | 0.29562 (3) | 0.06015 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0449 (9) | 0.0673 (11) | 0.0729 (12) | 0.0299 (8) | 0.0284 (9) | 0.0261 (10) |
C2 | 0.0416 (9) | 0.0683 (11) | 0.0637 (11) | 0.0266 (8) | 0.0135 (8) | 0.0288 (9) |
C3 | 0.0461 (9) | 0.0519 (9) | 0.0440 (9) | 0.0186 (7) | 0.0162 (7) | 0.0188 (7) |
C4 | 0.0365 (7) | 0.0354 (7) | 0.0411 (8) | 0.0135 (6) | 0.0150 (6) | 0.0133 (6) |
C5 | 0.0414 (8) | 0.0436 (8) | 0.0402 (8) | 0.0186 (6) | 0.0178 (6) | 0.0129 (6) |
C6 | 0.0353 (7) | 0.0388 (7) | 0.0350 (7) | 0.0145 (6) | 0.0121 (6) | 0.0112 (6) |
C7 | 0.0441 (8) | 0.0555 (9) | 0.0407 (8) | 0.0222 (7) | 0.0208 (7) | 0.0136 (7) |
C8 | 0.0492 (9) | 0.0662 (11) | 0.0403 (8) | 0.0203 (8) | 0.0202 (7) | 0.0196 (8) |
C9 | 0.0443 (9) | 0.0593 (10) | 0.0441 (9) | 0.0180 (7) | 0.0143 (7) | 0.0254 (8) |
C10 | 0.0375 (8) | 0.0491 (9) | 0.0450 (8) | 0.0186 (7) | 0.0121 (6) | 0.0188 (7) |
C11 | 0.0313 (7) | 0.0406 (7) | 0.0388 (8) | 0.0144 (6) | 0.0122 (6) | 0.0123 (6) |
C12 | 0.0336 (7) | 0.0381 (7) | 0.0362 (7) | 0.0138 (6) | 0.0118 (6) | 0.0108 (6) |
C13 | 0.0361 (7) | 0.0433 (8) | 0.0376 (7) | 0.0155 (6) | 0.0149 (6) | 0.0128 (6) |
C14 | 0.0475 (9) | 0.0436 (8) | 0.0486 (9) | 0.0132 (7) | 0.0208 (7) | 0.0138 (7) |
C15 | 0.0583 (11) | 0.0594 (11) | 0.0618 (11) | 0.0183 (9) | 0.0289 (9) | 0.0321 (9) |
C16 | 0.0769 (13) | 0.0819 (13) | 0.0482 (10) | 0.0350 (11) | 0.0344 (10) | 0.0316 (10) |
C17 | 0.1087 (18) | 0.0660 (12) | 0.0474 (10) | 0.0396 (12) | 0.0364 (11) | 0.0143 (9) |
C18 | 0.0849 (13) | 0.0458 (9) | 0.0465 (9) | 0.0279 (9) | 0.0294 (9) | 0.0158 (8) |
C19 | 0.0444 (9) | 0.0609 (11) | 0.0660 (11) | 0.0270 (8) | 0.0232 (8) | 0.0203 (9) |
C20 | 0.0507 (9) | 0.0506 (9) | 0.0556 (10) | 0.0228 (8) | 0.0141 (8) | 0.0218 (8) |
C21 | 0.0479 (9) | 0.0520 (9) | 0.0519 (9) | 0.0164 (7) | 0.0218 (8) | 0.0245 (8) |
C22 | 0.0350 (7) | 0.0393 (7) | 0.0351 (7) | 0.0098 (6) | 0.0124 (6) | 0.0092 (6) |
C23 | 0.0345 (7) | 0.0420 (8) | 0.0433 (8) | 0.0105 (6) | 0.0146 (6) | 0.0128 (6) |
C24 | 0.0324 (7) | 0.0387 (7) | 0.0371 (7) | 0.0094 (6) | 0.0101 (6) | 0.0127 (6) |
C25 | 0.0472 (9) | 0.0529 (9) | 0.0465 (9) | 0.0130 (7) | 0.0214 (7) | 0.0169 (7) |
C26 | 0.0610 (11) | 0.0608 (10) | 0.0435 (9) | 0.0105 (9) | 0.0206 (8) | 0.0207 (8) |
C27 | 0.0575 (10) | 0.0612 (11) | 0.0479 (10) | 0.0102 (9) | 0.0092 (8) | 0.0281 (8) |
C28 | 0.0435 (9) | 0.0555 (10) | 0.0531 (10) | 0.0161 (7) | 0.0108 (7) | 0.0253 (8) |
C29 | 0.0348 (7) | 0.0384 (7) | 0.0427 (8) | 0.0098 (6) | 0.0098 (6) | 0.0130 (6) |
C30 | 0.0327 (7) | 0.0377 (7) | 0.0385 (8) | 0.0103 (6) | 0.0108 (6) | 0.0110 (6) |
C31 | 0.0409 (8) | 0.0375 (7) | 0.0405 (8) | 0.0146 (6) | 0.0169 (6) | 0.0129 (6) |
C32 | 0.0461 (9) | 0.0614 (10) | 0.0421 (9) | 0.0090 (8) | 0.0145 (7) | 0.0111 (8) |
C33 | 0.0685 (12) | 0.0732 (12) | 0.0387 (9) | 0.0171 (10) | 0.0125 (9) | 0.0122 (9) |
C34 | 0.0918 (15) | 0.0595 (11) | 0.0489 (10) | 0.0305 (10) | 0.0372 (10) | 0.0221 (9) |
C35 | 0.0667 (12) | 0.0613 (11) | 0.0709 (12) | 0.0275 (9) | 0.0448 (10) | 0.0313 (10) |
C36 | 0.0446 (9) | 0.0527 (9) | 0.0574 (10) | 0.0192 (7) | 0.0227 (8) | 0.0216 (8) |
N1 | 0.0373 (6) | 0.0397 (6) | 0.0426 (7) | 0.0183 (5) | 0.0138 (5) | 0.0115 (5) |
N2 | 0.0332 (6) | 0.0419 (7) | 0.0348 (6) | 0.0165 (5) | 0.0126 (5) | 0.0124 (5) |
N3 | 0.0373 (6) | 0.0457 (7) | 0.0398 (7) | 0.0200 (5) | 0.0151 (5) | 0.0154 (5) |
N4 | 0.0350 (6) | 0.0454 (7) | 0.0402 (7) | 0.0148 (5) | 0.0131 (5) | 0.0126 (6) |
N5 | 0.0347 (6) | 0.0387 (6) | 0.0366 (6) | 0.0093 (5) | 0.0116 (5) | 0.0123 (5) |
N6 | 0.0389 (7) | 0.0471 (7) | 0.0440 (7) | 0.0171 (6) | 0.0138 (6) | 0.0162 (6) |
S1 | 0.0535 (3) | 0.0629 (3) | 0.0473 (2) | 0.0285 (2) | 0.02553 (19) | 0.0213 (2) |
S2 | 0.0585 (3) | 0.0798 (3) | 0.0735 (3) | 0.0368 (2) | 0.0419 (2) | 0.0458 (3) |
C1—C2 | 1.341 (3) | C19—C20 | 1.337 (2) |
C1—S1 | 1.7096 (17) | C19—S2 | 1.7105 (17) |
C1—H1 | 0.9300 | C19—H19 | 0.9300 |
C2—C3 | 1.411 (2) | C20—C21 | 1.409 (2) |
C2—H2 | 0.9300 | C20—H20 | 0.9300 |
C3—C4 | 1.371 (2) | C21—C22 | 1.366 (2) |
C3—H3 | 0.9300 | C21—H21 | 0.9300 |
C4—C5 | 1.4392 (19) | C22—C23 | 1.4376 (19) |
C4—S1 | 1.7145 (15) | C22—S2 | 1.7100 (15) |
C5—N1 | 1.2801 (18) | C23—N4 | 1.2860 (18) |
C5—H5 | 0.9300 | C23—H23 | 0.9300 |
C6—N1 | 1.3799 (17) | C24—N4 | 1.3806 (18) |
C6—N2 | 1.3941 (18) | C24—C30 | 1.387 (2) |
C6—C12 | 1.395 (2) | C24—N5 | 1.3891 (18) |
C7—C8 | 1.351 (2) | C25—C26 | 1.354 (2) |
C7—N2 | 1.3703 (19) | C25—N5 | 1.3697 (19) |
C7—H7 | 0.9300 | C25—H25 | 0.9300 |
C8—C9 | 1.415 (2) | C26—C27 | 1.413 (3) |
C8—H8 | 0.9300 | C26—H26 | 0.9300 |
C9—C10 | 1.355 (2) | C27—C28 | 1.354 (2) |
C9—H9 | 0.9300 | C27—H27 | 0.9300 |
C10—C11 | 1.4088 (19) | C28—C29 | 1.412 (2) |
C10—H10 | 0.9300 | C28—H28 | 0.9300 |
C11—N3 | 1.3242 (18) | C29—N6 | 1.324 (2) |
C11—N2 | 1.3898 (17) | C29—N5 | 1.3880 (18) |
C12—N3 | 1.3739 (17) | C30—N6 | 1.3743 (18) |
C12—C13 | 1.471 (2) | C30—C31 | 1.473 (2) |
C13—C18 | 1.390 (2) | C31—C36 | 1.388 (2) |
C13—C14 | 1.393 (2) | C31—C32 | 1.393 (2) |
C14—C15 | 1.379 (2) | C32—C33 | 1.381 (2) |
C14—H14 | 0.9300 | C32—H32 | 0.9300 |
C15—C16 | 1.376 (3) | C33—C34 | 1.372 (3) |
C15—H15 | 0.9300 | C33—H33 | 0.9300 |
C16—C17 | 1.376 (3) | C34—C35 | 1.372 (3) |
C16—H16 | 0.9300 | C34—H34 | 0.9300 |
C17—C18 | 1.382 (2) | C35—C36 | 1.383 (2) |
C17—H17 | 0.9300 | C35—H35 | 0.9300 |
C18—H18 | 0.9300 | C36—H36 | 0.9300 |
C2—C1—S1 | 112.04 (13) | C22—C21—C20 | 113.05 (15) |
C2—C1—H1 | 124.0 | C22—C21—H21 | 123.5 |
S1—C1—H1 | 124.0 | C20—C21—H21 | 123.5 |
C1—C2—C3 | 112.84 (15) | C21—C22—C23 | 127.71 (14) |
C1—C2—H2 | 123.6 | C21—C22—S2 | 110.50 (11) |
C3—C2—H2 | 123.6 | C23—C22—S2 | 121.79 (11) |
C4—C3—C2 | 112.60 (15) | N4—C23—C22 | 121.71 (14) |
C4—C3—H3 | 123.7 | N4—C23—H23 | 119.1 |
C2—C3—H3 | 123.7 | C22—C23—H23 | 119.1 |
C3—C4—C5 | 127.09 (14) | N4—C24—C30 | 138.57 (13) |
C3—C4—S1 | 110.75 (11) | N4—C24—N5 | 116.60 (13) |
C5—C4—S1 | 121.90 (11) | C30—C24—N5 | 104.83 (12) |
N1—C5—C4 | 121.22 (14) | C26—C25—N5 | 118.84 (16) |
N1—C5—H5 | 119.4 | C26—C25—H25 | 120.6 |
C4—C5—H5 | 119.4 | N5—C25—H25 | 120.6 |
N1—C6—N2 | 114.96 (12) | C25—C26—C27 | 120.38 (17) |
N1—C6—C12 | 139.56 (13) | C25—C26—H26 | 119.8 |
N2—C6—C12 | 104.65 (11) | C27—C26—H26 | 119.8 |
C8—C7—N2 | 118.79 (14) | C28—C27—C26 | 120.69 (15) |
C8—C7—H7 | 120.6 | C28—C27—H27 | 119.7 |
N2—C7—H7 | 120.6 | C26—C27—H27 | 119.7 |
C7—C8—C9 | 120.61 (15) | C27—C28—C29 | 119.54 (16) |
C7—C8—H8 | 119.7 | C27—C28—H28 | 120.2 |
C9—C8—H8 | 119.7 | C29—C28—H28 | 120.2 |
C10—C9—C8 | 120.48 (14) | N6—C29—N5 | 111.06 (12) |
C10—C9—H9 | 119.8 | N6—C29—C28 | 131.03 (15) |
C8—C9—H9 | 119.8 | N5—C29—C28 | 117.90 (14) |
C9—C10—C11 | 119.51 (14) | N6—C30—C24 | 110.99 (13) |
C9—C10—H10 | 120.2 | N6—C30—C31 | 119.15 (12) |
C11—C10—H10 | 120.2 | C24—C30—C31 | 129.83 (13) |
N3—C11—N2 | 111.13 (12) | C36—C31—C32 | 118.32 (15) |
N3—C11—C10 | 130.72 (13) | C36—C31—C30 | 119.20 (14) |
N2—C11—C10 | 118.12 (13) | C32—C31—C30 | 122.42 (14) |
N3—C12—C6 | 110.91 (13) | C33—C32—C31 | 120.55 (17) |
N3—C12—C13 | 118.49 (12) | C33—C32—H32 | 119.7 |
C6—C12—C13 | 130.57 (12) | C31—C32—H32 | 119.7 |
C18—C13—C14 | 118.35 (14) | C34—C33—C32 | 120.47 (18) |
C18—C13—C12 | 118.66 (14) | C34—C33—H33 | 119.8 |
C14—C13—C12 | 122.94 (14) | C32—C33—H33 | 119.8 |
C15—C14—C13 | 120.75 (16) | C35—C34—C33 | 119.64 (17) |
C15—C14—H14 | 119.6 | C35—C34—H34 | 120.2 |
C13—C14—H14 | 119.6 | C33—C34—H34 | 120.2 |
C16—C15—C14 | 120.28 (16) | C34—C35—C36 | 120.55 (17) |
C16—C15—H15 | 119.9 | C34—C35—H35 | 119.7 |
C14—C15—H15 | 119.9 | C36—C35—H35 | 119.7 |
C15—C16—C17 | 119.66 (17) | C35—C36—C31 | 120.47 (16) |
C15—C16—H16 | 120.2 | C35—C36—H36 | 119.8 |
C17—C16—H16 | 120.2 | C31—C36—H36 | 119.8 |
C16—C17—C18 | 120.48 (18) | C5—N1—C6 | 123.72 (13) |
C16—C17—H17 | 119.8 | C7—N2—C11 | 122.48 (12) |
C18—C17—H17 | 119.8 | C7—N2—C6 | 130.34 (12) |
C17—C18—C13 | 120.45 (16) | C11—N2—C6 | 107.15 (11) |
C17—C18—H18 | 119.8 | C11—N3—C12 | 106.14 (12) |
C13—C18—H18 | 119.8 | C23—N4—C24 | 120.64 (13) |
C20—C19—S2 | 111.98 (13) | C25—N5—C29 | 122.62 (13) |
C20—C19—H19 | 124.0 | C25—N5—C24 | 130.14 (13) |
S2—C19—H19 | 124.0 | C29—N5—C24 | 107.17 (12) |
C19—C20—C21 | 112.60 (15) | C29—N6—C30 | 105.92 (12) |
C19—C20—H20 | 123.7 | C1—S1—C4 | 91.78 (8) |
C21—C20—H20 | 123.7 | C22—S2—C19 | 91.88 (8) |
Cg1 and Cg2 are the centroids of the C31–C36 and C13–C18 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19···N3i | 0.93 | 2.50 | 3.428 (2) | 175 |
C14—H14···N6ii | 0.93 | 2.61 | 3.526 (2) | 170 |
C15—H15···Cg1ii | 0.93 | 2.97 | 3.778 (2) | 146 |
C18—H18···Cg1 | 0.93 | 2.88 | 3.761 (2) | 157 |
C33—H33···Cg2iii | 0.93 | 2.95 | 3.814 (2) | 155 |
Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z; (iii) −x+1, −y+1, −z. |
Cg1 and Cg2 are the centroids of the C31–C36 and C13–C18 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19···N3i | 0.93 | 2.50 | 3.428 (2) | 174.5 |
C14—H14···N6ii | 0.93 | 2.61 | 3.526 (2) | 170.3 |
C15—H15···Cg1ii | 0.93 | 2.97 | 3.778 (2) | 146 |
C18—H18···Cg1 | 0.93 | 2.88 | 3.761 (2) | 157 |
C33—H33···Cg2iii | 0.93 | 2.95 | 3.814 (2) | 155 |
Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z; (iii) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C18H13N3S |
Mr | 303.37 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 9.6524 (17), 10.1168 (17), 16.655 (3) |
α, β, γ (°) | 101.299 (8), 106.315 (9), 95.628 (8) |
V (Å3) | 1510.3 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.44 × 0.21 × 0.12 |
Data collection | |
Diffractometer | Bruker X8 APEX |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.641, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 66495, 8471, 5839 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.694 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.125, 1.02 |
No. of reflections | 8471 |
No. of parameters | 397 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.48 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS2014 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Acknowledgements
The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.
References
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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.
Schiff bases bearing an azomethine functional group –C═N–, have gained importance in pharmaceutical and medicinal industries due to their widespread potential biological activities such as anticancer (Ren et al., 2002), antibacterial and antifungal activities (Shi et al., 2007), anticonvulsant (Sridhar et al., 2002, Kaplan et al., 1980), antituberculosis (Patole et al., 2006 Hearn & Cynamon, 2004), analgesic and anti-inflammatory properties (Bhandari et al., 2008). The present paper is a continuation of our research work devoted to the development of the imidazo [1,2a]pyridine derivatives with potential pharmacological activities (Elaatiaoui et al., 2014; Elaatiaoui et al., 2015).
The heterobicyclic ring system in the title compound is essentially planar, with a maximum deviation of 0.022 (1)Å for C6 atom in the first molecule (S1/N1/N2/N3/ C1 to C18) and 0.018 (1)Å for N5 in the second molecule (S2/N4/N5N6 C19 to C36) (Fig. 1). In the first molecule, the dihedral angles between the mean plane through the fused rings system (N2/N3 C6 to C12) and the thiophen-2-yl (S1, C1 to C4) and the phenyl (C13 to C18) rings are of 24.06 (7)° and 40.52 (8)°, respectively. Nearly the same values are observed in the second molecule between the imidazo[1,2-a]pyridin system and the thiophen-2-yl (S2, C19 to C22) and the phenyl (C31 to C36) rings namely 25.20 (7)° and 38.99 (7)°, respectively. Moreover, the dihedral angle between the thiophen-2-yl and the phenyl rings is of 63.47 (9)° in the first molecule and 47.49 (9)° in the second.
In the crystal, molecules are linked together by two C–H···N hydrogen bonds between molecules and by C–H···π interactions, forming a three dimensional network (Fig. 3 and Table 1).