Abstract
C14H12N2O2, monoclinic, P21, a = 8.3844(1) Å, b = 20.0465(3) Å, c = 14.0511(2) Å, β = 94.786(1)°, V = 2353.44(6) Å3, Z = 4, Rgt(F) = 0.0356, wRref(F2) = 0.1022, T = 150(2) K.
The crystal structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.
Crystal: | Yellow block |
Size: | 0.25 × 0.21 × 0.13 mm |
Wavelength: | Mo Kα radiation (0.71073 Å) |
μ: | 0.09 mm−1 |
Diffractometer, scan mode: | Bruker APEX-II, φ and ω-scans |
θmax, completeness: | 27°, >99% |
N(hkl)measured, N(hkl)unique, Rint: | 14543, 9464, 0.013 |
Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 8295 |
N(param)refined: | 653 |
Programs: | Bruker programs [1], SHELX [2], [3], Mercury [4] |
Atom | x | y | z | Uiso*/Ueq |
---|---|---|---|---|
O1A | 0.4015(2) | 0.55500(12) | 0.37669(13) | 0.0412(5) |
O2A | 0.5065(3) | 0.62258(15) | 0.2793(2) | 0.0463(7) |
N1A | 0.1639(3) | 0.40462(12) | 0.32621(16) | 0.0268(5) |
N2A | 0.4102(3) | 0.57940(14) | 0.2971(2) | 0.0295(6) |
C1A | −0.0121(4) | 0.2835(2) | 0.3225(3) | 0.0354(8) |
H1AA | 0.035361 | 0.278918 | 0.261464 | 0.053* |
H1AB | −0.089541 | 0.320229 | 0.318349 | 0.053* |
H1AC | −0.066653 | 0.241933 | 0.337057 | 0.053* |
C2A | 0.1163(4) | 0.29782(18) | 0.3997(3) | 0.0284(7) |
C3A | 0.1524(5) | 0.25363(18) | 0.4753(2) | 0.0319(8) |
H3A | 0.090519 | 0.214086 | 0.478350 | 0.038* |
C4A | 0.2731(5) | 0.26488(18) | 0.5454(3) | 0.0334(8) |
H4A | 0.294676 | 0.233351 | 0.595261 | 0.040* |
C5A | 0.3639(5) | 0.32295(18) | 0.5428(3) | 0.0326(8) |
H5A | 0.448144 | 0.331089 | 0.590860 | 0.039* |
C6A | 0.3313(4) | 0.36882(16) | 0.4700(2) | 0.0274(7) |
H6A | 0.392737 | 0.408581 | 0.468839 | 0.033* |
C7A | 0.2092(4) | 0.35717(15) | 0.3985(2) | 0.0236(7) |
C8A | 0.2696(4) | 0.44361(15) | 0.29730(18) | 0.0257(6) |
H8A | 0.377908 | 0.439977 | 0.322627 | 0.031* |
C10A | 0.2942(4) | 0.55774(17) | 0.2196(2) | 0.0243(7) |
C11A | 0.2541(4) | 0.60282(17) | 0.1475(3) | 0.0291(7) |
H11A | 0.305097 | 0.645116 | 0.147011 | 0.035* |
C12A | 0.1381(4) | 0.5855(2) | 0.0758(2) | 0.0318(7) |
H12A | 0.108913 | 0.615832 | 0.025413 | 0.038* |
C13A | 0.0652(5) | 0.5239(2) | 0.0778(3) | 0.0347(8) |
H13A | −0.014547 | 0.512061 | 0.028691 | 0.042* |
C14A | 0.1070(4) | 0.47888(19) | 0.1511(2) | 0.0293(7) |
H14A | 0.055429 | 0.436694 | 0.151183 | 0.035* |
O1B | 0.3488(2) | 0.44289(13) | −0.12691(13) | 0.0408(5) |
O2B | 0.2402(3) | 0.37674(14) | −0.0293(2) | 0.0439(7) |
N1B | 0.5896(3) | 0.59253(12) | −0.07785(16) | 0.0266(5) |
N2B | 0.3388(3) | 0.41924(15) | −0.0475(2) | 0.0307(6) |
C1B | 0.7740(5) | 0.7122(2) | −0.0734(3) | 0.0412(9) |
H1BA | 0.737180 | 0.745292 | −0.028744 | 0.062* |
H1BB | 0.868060 | 0.729522 | −0.102284 | 0.062* |
H1BC | 0.802447 | 0.670832 | −0.038929 | 0.062* |
C2B | 0.6411(4) | 0.69831(18) | −0.1512(3) | 0.0281(7) |
C3B | 0.6077(5) | 0.74462(19) | −0.2248(3) | 0.0358(9) |
H3B | 0.669126 | 0.784399 | −0.225711 | 0.043* |
C4B | 0.4865(5) | 0.7335(2) | −0.2964(3) | 0.0404(10) |
H4B | 0.465900 | 0.765203 | −0.346112 | 0.048* |
C5B | 0.3961(5) | 0.67606(19) | −0.2951(3) | 0.0362(8) |
H5B | 0.312687 | 0.668318 | −0.343823 | 0.043* |
C6B | 0.4266(4) | 0.62982(18) | −0.2230(2) | 0.0299(7) |
H6B | 0.364533 | 0.590206 | −0.222557 | 0.036* |
C7B | 0.5493(4) | 0.64117(17) | −0.1504(2) | 0.0261(7) |
C8B | 0.4833(3) | 0.55495(15) | −0.04935(19) | 0.0253(6) |
H8B | 0.375409 | 0.559104 | −0.075268 | 0.030* |
C9B | 0.5273(4) | 0.50392(16) | 0.0252(2) | 0.0227(7) |
C10B | 0.4553(4) | 0.44168(17) | 0.0298(2) | 0.0239(7) |
C11B | 0.4945(4) | 0.39617(16) | 0.1030(2) | 0.0277(7) |
H11B | 0.442460 | 0.354114 | 0.103916 | 0.033* |
C12B | 0.6108(4) | 0.4135(2) | 0.1743(2) | 0.0317(7) |
H12B | 0.639189 | 0.383319 | 0.225068 | 0.038* |
C13B | 0.6859(4) | 0.4750(2) | 0.1716(2) | 0.0313(8) |
H13B | 0.766594 | 0.486544 | 0.220334 | 0.038* |
C14B | 0.6446(4) | 0.51962(18) | 0.0987(2) | 0.0294(7) |
H14B | 0.696743 | 0.561692 | 0.098405 | 0.035* |
O1C | 0.0060(2) | 0.52358(13) | −0.14939(13) | 0.0410(5) |
O2C | 0.0113(4) | 0.62417(15) | −0.2026(3) | 0.0552(8) |
N1C | −0.2910(3) | 0.38935(12) | −0.18932(16) | 0.0254(5) |
N2C | −0.0470(3) | 0.56852(14) | −0.20288(19) | 0.0308(6) |
C1C | −0.5187(4) | 0.2845(2) | −0.1814(3) | 0.0369(8) |
H1CA | −0.561627 | 0.239262 | −0.177192 | 0.055* |
H1CB | −0.474432 | 0.290408 | −0.243272 | 0.055* |
H1CC | −0.604727 | 0.316997 | −0.175393 | 0.055* |
C2C | −0.3904(4) | 0.29512(17) | −0.1032(3) | 0.0283(7) |
C3C | −0.3739(5) | 0.25360(18) | −0.0231(3) | 0.0328(8) |
H3C | −0.448291 | 0.218263 | −0.018322 | 0.039* |
C4C | −0.2548(5) | 0.26174(18) | 0.0490(3) | 0.0348(8) |
H4C | −0.247465 | 0.232460 | 0.102397 | 0.042* |
C5C | −0.1451(5) | 0.31315(19) | 0.0433(3) | 0.0341(8) |
H5C | −0.061836 | 0.318885 | 0.092781 | 0.041* |
C6C | −0.1566(4) | 0.35630(17) | −0.0344(2) | 0.0272(7) |
H6C | −0.080465 | 0.391092 | −0.038181 | 0.033* |
C7C | −0.2790(4) | 0.34877(15) | −0.1067(2) | 0.0225(6) |
C8C | −0.2624(3) | 0.45148(15) | −0.1785(2) | 0.0240(6) |
H8C | −0.232616 | 0.468866 | −0.116658 | 0.029* |
C9C | −0.2756(4) | 0.49630(16) | −0.2618(2) | 0.0238(7) |
C10C | −0.1826(4) | 0.55382(17) | −0.2721(2) | 0.0251(7) |
C11C | - 0.2082(4) | 0.59679(18) | −0.3480(3) | 0.0323(8) |
H11C | −0.144153 | 0.635648 | −0.351797 | 0.039* |
C12C | −0.3283(4) | 0.5829(2) | −0.4190(2) | 0.0327(8) |
H12C | −0.347264 | 0.612118 | −0.471925 | 0.039* |
C13C | −0.4200(4) | 0.5265(2) | −0.4123(2) | 0.0327(8) |
H13C | −0.501370 | 0.516528 | −0.461431 | 0.039* |
C14C | −0.3950(4) | 0.48389(17) | −0.3348(2) | 0.0266(7) |
H14C | −0.460608 | 0.445476 | −0.331263 | 0.032* |
O1D | −0.2547(2) | 0.46948(12) | −0.59930(13) | 0.0396(5) |
O2D | −0.2554(4) | 0.36818(14) | −0.5488(2) | 0.0505(7) |
N1D | 0.0371(3) | 0.60515(12) | −0.55713(16) | 0.0248(5) |
N2D | −0.1996(3) | 0.42452(15) | −0.5473(2) | 0.0304(6) |
C1D | 0.2644(4) | 0.7109(2) | −0.5656(3) | 0.0354(8) |
H1DA | 0.223232 | 0.738723 | −0.515688 | 0.053* |
H1DB | 0.354379 | 0.733681 | −0.591855 | 0.053* |
H1DC | 0.300545 | 0.668050 | −0.538146 | 0.053* |
C2D | 0.1324(4) | 0.69913(17) | −0.6447(2) | 0.0252(7) |
C3D | 0.1152(5) | 0.74168(18) | −0.7234(3) | 0.0317(8) |
H3D | 0.187856 | 0.777729 | −0.727599 | 0.038* |
C4D | −0.0060(5) | 0.73235(19) | −0.7958(3) | 0.0352(9) |
H4D | −0.014867 | 0.761420 | - 0.849382 | 0.042* |
C5D | −0.1135(5) | 0.68070(18) | −0.7896(3) | 0.0321(8) |
H5D | −0.197030 | 0.674270 | −0.838694 | 0.039* |
C6D | −0.0993(4) | 0.63846(17) | −0.7119(2) | 0.0281(7) |
H6D | −0.173984 | 0.603204 | −0.707312 | 0.034* |
C7D | 0.0247(4) | 0.64717(16) | −0.6395(2) | 0.0243(6) |
C8D | 0.0110(3) | 0.54362(14) | −0.56873(19) | 0.0226(6) |
H8D | −0.017620 | 0.526500 | −0.630852 | 0.027* |
C9D | 0.0252(4) | 0.49789(16) | −0.4853(2) | 0.0217(6) |
C10D | −0.0647(4) | 0.44009(17) | −0.4770(2) | 0.0238(7) |
C11D | −0.0384(4) | 0.39611(17) | −0.4002(3) | 0.0299(7) |
H11D | −0.101405 | 0.356934 | −0.396863 | 0.036* |
C12D | 0.0807(4) | 0.4105(2) | −0.3292(3) | 0.0338(8) |
H12D | 0.100686 | 0.380960 | −0.276681 | 0.041* |
C13D | 0.1713(4) | 0.4682(2) | −0.3349(2) | 0.0316(8) |
H13D | 0.252138 | 0.478449 | −0.285662 | 0.038* |
C14D | 0.1445(4) | 0.51060(18) | −0.4116(2) | 0.0291(7) |
H14D | 0.208492 | 0.549517 | −0.414633 | 0.035* |
Source of material
The title compound was synthesized via a solvent free approach by stirring equimolar o-toluidine (0.11 g, 1.0 mmol) and 2-nitrobenzaldehyde (0.1 g, 1.0 mmol) in a poly top vial for 5 minutes using a glass rod to yield a yellow compound. Rectangular crystals suitable for X-ray diffraction were obtained by slow evaporation from diethylether within 48 h. Yield = 0.23 g (96%), 1H NMR (400 MHz, Chloroform-d) δ 8.83 (s, 1H), 8.32 (dd, J = 7.8 Hz, 1H), 8.06 (dd, J = 8.2 Hz, 1H), 7.74 (t, J = 7.6 Hz, 1H), 7.62 (td, J = 7.8 Hz, 1H), 7.23 (d, J = 6.6 Hz, 3H), 7.21–7.13 (m, 1H), 7.05–6.99 (m, 1H), 2.40 (s, 3H). 13C NMR (400 MHz, Chloroform-d) δ = 155.04, 150.18, 149.35, 133.51, 132.27, 131.29, 131.08, 130.44, 129.89, 126.90, 126.62, 124.50, 117.84, 17.87. C14H12N2O2 Calcd: C = 69.99%, H = 5.03%, N = 11.66%; Found: C = 70.01%, H = 5.10%, N = 11.30%.
Experimental details
The structure was solved by the intrinsic phasing using the SHELXT [2] program and refined using SHELXL [3]. The visual crystal structure information was performed using Mercury [4]. All C—Haromatic and O—H bond distances were restrained to 0.95 Å, 0.98 Å and 0.99 Å with Uiso(Haromatic) = 1.2Ueq and Uiso(Hhydroxyl) = 1.5Ueq of parent atom, respectively.
Discussion
Schiff bases are organic compounds with an azomethine or imine (—C=N—) functional group, where the imine nitrogen atom can be linked to different groups such as alkyl, cycloalkyl, aryl or heterocyclic groups, but not hydrogen atom [5]. They are well known for their significant biological activities such as antioxidant [6], [7], antibacterial [5], [8], antifungal [9], [10], and anticancer agents [11], [12]. Other applications also include, as sensors [13], [14], corrosion inhibitors [15], [16] and chelating ligands in coordination chemistry [17], [18]. The condensation reaction between primary amines (R-NH2), with active carbonyl compounds (aldehyde or ketone), affords Schiff bases [19], [20], [21]. Schiff bases with aryl substituents are relatively stable and easy to prepare when compared with those that have alkyl substituents and during condensation reactions, aldehydes react faster than ketones [22]. The title compound has been synthesized by Zhou et al. [23] using the conventional method. We now report a solvent-free approach via mechanochemistry techniques. Aside from being a greener approach, the mechanochemistry method (grinding) also afforded the product within 5 minutes and even higher yield when compared to the one reported in the literature [23].
The crystal structure of the title compound has four symmetrically non-equivalent molecules in the asymmetric unit. The molecular units have similar conformation with dihedral angle between the anilyl and phenyl rings ranging from 5.2(1)° to 6.4(1)°, which is slightly wider than that observed in (E)-1-(2-nitrophenyl)-N-(p-tolyl)methanimine (3.09(8)°) [24]. All intramolecular bond parameters are comparable with closely related compounds in literature [25], [26], [27], [28], [29], [30], [31]. Non-classical intermolecular C—H⋯O hydrogen bonding exist between the aromatic hydrogens (H13A-D) and the nitro group’s oxygen atom (O1A-D). This forms chains which extends diagonally with respect to the crystallographic a and c axes. Intermolecular π⋯π interactions were also observed in the crystal packing of the title compound.
Acknowledgements
We thank Ekiti state university and TETFUND for research grant and University of KwaZulu-Natal for the providing the research facilities.
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