organic compounds
3-(4-Chlorophenyl)-5-phenyl-4,5-dihydro-1,3-oxazole
aNational Institute of Technology-Karnataka, Department of Chemistry, Medicinal Chemistry Laboratory, Surathkal, Mangalore 575 025, India, and bNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
*Correspondence e-mail: richard.betz@webmail.co.za
In the title compound, C15H12ClNO, the isoxazoline ring adopts an with the C atom bearing an unsubstituted phenyl ring as the flap atom. The chlorinated phenyl group is nearly in-plane with the four coplanar atoms of the heterocycle and the corresponding mean planes enclosing an angle of 1.16 (7)°. The unsubstituted phenyl group attached to the envelope flap atom approaches a nearly perpendicular orientation relative to the isoxazoline ring with a dihedral angle of 74.93 (7)°. In the crystal, weak C—H⋯O, C—H⋯N and C—H⋯π interactions connect the molecules into layers perpendicular to the a axis.
Related literature
For the biological and medicinal importance of isoxazole compounds, see: Miller et al. (2009); Prasad et al. (2007). For their use in ring-opening polymerizations, see: Wiesbrock et al. (2005). For the puckering analysis of five-membered rings, see: Cremer & Pople (1975). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).
Experimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2010); cell SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812043711/gk2526sup1.cif
contains datablocks I, global. DOI:Supporting information file. DOI: 10.1107/S1600536812043711/gk2526Isup2.cdx
Structure factors: contains datablock I. DOI: 10.1107/S1600536812043711/gk2526Isup3.hkl
Supporting information file. DOI: 10.1107/S1600536812043711/gk2526Isup4.cml
An equimolar mixture of 1-(4-chlorophenyl)-N-hydroxymethanimine (0.5 g, 0.0032 mol), N-chloro succinamide (0.58 g, 0.0032 mol) and sodium bicarbonate (0.537 g, 0,0064 mol) in dichloromethane (10 ml) and water (10 ml) was stirred at 0 °C for 1 h. Styrene (0.366 g, 0.0035 mol) was then added to the reaction mixture and stirring was continued for another 12 h at room temperature. After completion of the reaction, the reaction mixture was concentrated and purified by
using petrol ether and ethyl acetate (v/v = 1:1) as the to afford the title compound as a white solid, yield: 0.63 g (76.8%) (ChemSpider ID: 10496235).Carbon-bound H atoms were placed in calculated positions (C—H 0.95 Å for aromatic carbon atoms, C—H 1.00 Å for methine groups and C—H 0.99 Å for methylene groups) and were included in the
in the riding model approximation, with U(H) set to 1.2Ueq(C).Data collection: APEX2 (Bruker, 2010); cell
SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).C15H12ClNO | F(000) = 1072 |
Mr = 257.71 | Dx = 1.361 Mg m−3 |
Monoclinic, C2/c | Melting point = 406–408 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71069 Å |
a = 29.797 (5) Å | Cell parameters from 7100 reflections |
b = 10.717 (5) Å | θ = 2.8–28.3° |
c = 8.086 (5) Å | µ = 0.29 mm−1 |
β = 103.088 (5)° | T = 200 K |
V = 2515 (2) Å3 | Block, colourless |
Z = 8 | 0.58 × 0.42 × 0.21 mm |
Bruker APEXII CCD diffractometer | 3132 independent reflections |
Radiation source: fine-focus sealed tube | 2637 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
ϕ and ω scans | θmax = 28.3°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −39→39 |
Tmin = 0.850, Tmax = 0.943 | k = −14→13 |
11843 measured reflections | l = −10→9 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0463P)2 + 1.7436P] where P = (Fo2 + 2Fc2)/3 |
3132 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C15H12ClNO | V = 2515 (2) Å3 |
Mr = 257.71 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 29.797 (5) Å | µ = 0.29 mm−1 |
b = 10.717 (5) Å | T = 200 K |
c = 8.086 (5) Å | 0.58 × 0.42 × 0.21 mm |
β = 103.088 (5)° |
Bruker APEXII CCD diffractometer | 3132 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 2637 reflections with I > 2σ(I) |
Tmin = 0.850, Tmax = 0.943 | Rint = 0.014 |
11843 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.31 e Å−3 |
3132 reflections | Δρmin = −0.23 e Å−3 |
163 parameters |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.047465 (13) | 0.13436 (5) | −0.07319 (6) | 0.06357 (16) | |
O1 | 0.30314 (3) | 0.00728 (10) | 0.48581 (13) | 0.0473 (3) | |
N1 | 0.25598 (4) | −0.00421 (12) | 0.40628 (16) | 0.0450 (3) | |
C1 | 0.24324 (4) | 0.09115 (11) | 0.31161 (15) | 0.0300 (2) | |
C2 | 0.28171 (4) | 0.18052 (11) | 0.30834 (17) | 0.0349 (3) | |
H2A | 0.2724 | 0.2680 | 0.3214 | 0.042* | |
H2B | 0.2931 | 0.1724 | 0.2029 | 0.042* | |
C3 | 0.31733 (5) | 0.13540 (12) | 0.46363 (16) | 0.0373 (3) | |
H3 | 0.3141 | 0.1857 | 0.5645 | 0.045* | |
C11 | 0.19537 (4) | 0.10199 (11) | 0.21455 (15) | 0.0295 (2) | |
C12 | 0.18093 (4) | 0.20517 (12) | 0.11130 (16) | 0.0346 (3) | |
H12 | 0.2025 | 0.2686 | 0.1017 | 0.042* | |
C13 | 0.13540 (5) | 0.21625 (13) | 0.02230 (17) | 0.0405 (3) | |
H13 | 0.1256 | 0.2869 | −0.0475 | 0.049* | |
C14 | 0.10459 (4) | 0.12302 (13) | 0.03681 (17) | 0.0389 (3) | |
C15 | 0.11790 (4) | 0.01975 (13) | 0.13904 (17) | 0.0388 (3) | |
H15 | 0.0962 | −0.0432 | 0.1484 | 0.047* | |
C16 | 0.16323 (4) | 0.00951 (12) | 0.22721 (17) | 0.0354 (3) | |
H16 | 0.1727 | −0.0612 | 0.2973 | 0.043* | |
C21 | 0.36712 (4) | 0.13532 (11) | 0.45344 (15) | 0.0321 (3) | |
C22 | 0.39722 (5) | 0.22193 (12) | 0.54584 (18) | 0.0409 (3) | |
H22 | 0.3864 | 0.2811 | 0.6151 | 0.049* | |
C23 | 0.44339 (5) | 0.22225 (14) | 0.5373 (2) | 0.0504 (4) | |
H23 | 0.4639 | 0.2825 | 0.5993 | 0.060* | |
C24 | 0.45938 (5) | 0.13514 (15) | 0.4389 (2) | 0.0491 (4) | |
H24 | 0.4909 | 0.1347 | 0.4339 | 0.059* | |
C25 | 0.42940 (5) | 0.04860 (15) | 0.3476 (2) | 0.0480 (3) | |
H25 | 0.4404 | −0.0113 | 0.2797 | 0.058* | |
C26 | 0.38362 (5) | 0.04870 (13) | 0.35468 (17) | 0.0399 (3) | |
H26 | 0.3632 | −0.0111 | 0.2913 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.03330 (19) | 0.0913 (3) | 0.0612 (3) | 0.01429 (18) | 0.00056 (16) | 0.0042 (2) |
O1 | 0.0324 (5) | 0.0532 (6) | 0.0521 (6) | −0.0033 (4) | 0.0008 (4) | 0.0226 (5) |
N1 | 0.0310 (6) | 0.0492 (7) | 0.0523 (7) | −0.0030 (5) | 0.0042 (5) | 0.0185 (6) |
C1 | 0.0321 (6) | 0.0295 (5) | 0.0294 (5) | 0.0008 (4) | 0.0095 (4) | 0.0000 (4) |
C2 | 0.0312 (6) | 0.0296 (6) | 0.0435 (7) | 0.0008 (5) | 0.0074 (5) | 0.0034 (5) |
C3 | 0.0353 (6) | 0.0426 (7) | 0.0338 (6) | −0.0007 (5) | 0.0076 (5) | −0.0058 (5) |
C11 | 0.0320 (5) | 0.0282 (5) | 0.0294 (5) | 0.0029 (4) | 0.0093 (4) | −0.0022 (4) |
C12 | 0.0383 (6) | 0.0325 (6) | 0.0343 (6) | 0.0027 (5) | 0.0108 (5) | 0.0022 (5) |
C13 | 0.0434 (7) | 0.0421 (7) | 0.0359 (6) | 0.0129 (6) | 0.0088 (5) | 0.0065 (5) |
C14 | 0.0304 (6) | 0.0504 (7) | 0.0355 (6) | 0.0099 (5) | 0.0066 (5) | −0.0044 (6) |
C15 | 0.0326 (6) | 0.0397 (7) | 0.0449 (7) | −0.0007 (5) | 0.0106 (5) | −0.0045 (5) |
C16 | 0.0347 (6) | 0.0306 (6) | 0.0413 (6) | 0.0023 (5) | 0.0092 (5) | 0.0028 (5) |
C21 | 0.0326 (6) | 0.0332 (6) | 0.0290 (5) | −0.0006 (4) | 0.0036 (4) | 0.0011 (5) |
C22 | 0.0439 (7) | 0.0338 (6) | 0.0428 (7) | −0.0031 (5) | 0.0054 (5) | −0.0050 (5) |
C23 | 0.0421 (8) | 0.0454 (8) | 0.0583 (9) | −0.0138 (6) | 0.0002 (6) | 0.0011 (7) |
C24 | 0.0320 (7) | 0.0534 (9) | 0.0615 (9) | 0.0014 (6) | 0.0099 (6) | 0.0110 (7) |
C25 | 0.0443 (8) | 0.0490 (8) | 0.0529 (8) | 0.0073 (6) | 0.0160 (6) | −0.0014 (7) |
C26 | 0.0385 (7) | 0.0413 (7) | 0.0390 (7) | −0.0019 (5) | 0.0069 (5) | −0.0068 (6) |
Cl1—C14 | 1.7372 (14) | C13—H13 | 0.9500 |
O1—N1 | 1.4121 (14) | C14—C15 | 1.385 (2) |
O1—C3 | 1.4597 (18) | C15—C16 | 1.3816 (18) |
N1—C1 | 1.2818 (17) | C15—H15 | 0.9500 |
C1—C11 | 1.4688 (16) | C16—H16 | 0.9500 |
C1—C2 | 1.4985 (17) | C21—C26 | 1.3853 (19) |
C2—C3 | 1.5277 (19) | C21—C22 | 1.3859 (18) |
C2—H2A | 0.9900 | C22—C23 | 1.393 (2) |
C2—H2B | 0.9900 | C22—H22 | 0.9500 |
C3—C21 | 1.5043 (18) | C23—C24 | 1.380 (2) |
C3—H3 | 1.0000 | C23—H23 | 0.9500 |
C11—C12 | 1.3936 (17) | C24—C25 | 1.380 (2) |
C11—C16 | 1.3979 (18) | C24—H24 | 0.9500 |
C12—C13 | 1.3893 (18) | C25—C26 | 1.378 (2) |
C12—H12 | 0.9500 | C25—H25 | 0.9500 |
C13—C14 | 1.380 (2) | C26—H26 | 0.9500 |
N1—O1—C3 | 108.20 (9) | C13—C14—Cl1 | 119.96 (11) |
C1—N1—O1 | 109.39 (10) | C15—C14—Cl1 | 118.45 (11) |
N1—C1—C11 | 120.17 (11) | C16—C15—C14 | 119.06 (12) |
N1—C1—C2 | 113.33 (11) | C16—C15—H15 | 120.5 |
C11—C1—C2 | 126.46 (10) | C14—C15—H15 | 120.5 |
C1—C2—C3 | 100.08 (10) | C15—C16—C11 | 120.79 (12) |
C1—C2—H2A | 111.8 | C15—C16—H16 | 119.6 |
C3—C2—H2A | 111.8 | C11—C16—H16 | 119.6 |
C1—C2—H2B | 111.8 | C26—C21—C22 | 119.26 (12) |
C3—C2—H2B | 111.8 | C26—C21—C3 | 121.01 (11) |
H2A—C2—H2B | 109.5 | C22—C21—C3 | 119.73 (12) |
O1—C3—C21 | 108.85 (10) | C21—C22—C23 | 120.04 (13) |
O1—C3—C2 | 103.42 (10) | C21—C22—H22 | 120.0 |
C21—C3—C2 | 117.74 (11) | C23—C22—H22 | 120.0 |
O1—C3—H3 | 108.8 | C24—C23—C22 | 120.07 (13) |
C21—C3—H3 | 108.8 | C24—C23—H23 | 120.0 |
C2—C3—H3 | 108.8 | C22—C23—H23 | 120.0 |
C12—C11—C16 | 118.86 (11) | C23—C24—C25 | 119.78 (14) |
C12—C11—C1 | 120.90 (11) | C23—C24—H24 | 120.1 |
C16—C11—C1 | 120.22 (11) | C25—C24—H24 | 120.1 |
C13—C12—C11 | 120.73 (12) | C26—C25—C24 | 120.30 (14) |
C13—C12—H12 | 119.6 | C26—C25—H25 | 119.8 |
C11—C12—H12 | 119.6 | C24—C25—H25 | 119.8 |
C14—C13—C12 | 118.98 (12) | C25—C26—C21 | 120.55 (13) |
C14—C13—H13 | 120.5 | C25—C26—H26 | 119.7 |
C12—C13—H13 | 120.5 | C21—C26—H26 | 119.7 |
C13—C14—C15 | 121.58 (12) | ||
C3—O1—N1—C1 | 13.27 (15) | C13—C14—C15—C16 | −0.6 (2) |
O1—N1—C1—C11 | −179.87 (10) | Cl1—C14—C15—C16 | 179.98 (10) |
O1—N1—C1—C2 | 2.47 (16) | C14—C15—C16—C11 | 0.26 (19) |
N1—C1—C2—C3 | −15.95 (14) | C12—C11—C16—C15 | 0.04 (18) |
C11—C1—C2—C3 | 166.57 (11) | C1—C11—C16—C15 | 178.79 (11) |
N1—O1—C3—C21 | −148.44 (11) | O1—C3—C21—C26 | 44.82 (16) |
N1—O1—C3—C2 | −22.50 (13) | C2—C3—C21—C26 | −72.34 (16) |
C1—C2—C3—O1 | 21.97 (12) | O1—C3—C21—C22 | −134.27 (12) |
C1—C2—C3—C21 | 142.02 (11) | C2—C3—C21—C22 | 108.56 (14) |
N1—C1—C11—C12 | 179.87 (12) | C26—C21—C22—C23 | 0.8 (2) |
C2—C1—C11—C12 | −2.81 (18) | C3—C21—C22—C23 | 179.87 (12) |
N1—C1—C11—C16 | 1.15 (18) | C21—C22—C23—C24 | −1.0 (2) |
C2—C1—C11—C16 | 178.47 (12) | C22—C23—C24—C25 | 0.7 (2) |
C16—C11—C12—C13 | 0.01 (18) | C23—C24—C25—C26 | −0.1 (2) |
C1—C11—C12—C13 | −178.73 (11) | C24—C25—C26—C21 | −0.1 (2) |
C11—C12—C13—C14 | −0.36 (19) | C22—C21—C26—C25 | −0.2 (2) |
C12—C13—C14—C15 | 0.7 (2) | C3—C21—C26—C25 | −179.31 (13) |
C12—C13—C14—Cl1 | −179.94 (10) |
Cg is the centroid of the C11–C16 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···N1i | 0.95 | 2.74 | 3.657 (2) | 163 |
C12—H12···O1i | 0.95 | 2.65 | 3.390 (2) | 135 |
C2—H2B···O1ii | 0.99 | 2.67 | 3.466 (2) | 138 |
C26—H26···O1ii | 0.95 | 2.70 | 3.431 (2) | 134 |
C22—H22···Cgiii | 0.95 | 2.81 | 3.721 (3) | 162 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x, −y, z−1/2; (iii) −x+1/2, −y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C15H12ClNO |
Mr | 257.71 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 200 |
a, b, c (Å) | 29.797 (5), 10.717 (5), 8.086 (5) |
β (°) | 103.088 (5) |
V (Å3) | 2515 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.58 × 0.42 × 0.21 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.850, 0.943 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11843, 3132, 2637 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.103, 1.03 |
No. of reflections | 3132 |
No. of parameters | 163 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.23 |
Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg is the centroid of the C11–C16 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···N1i | 0.95 | 2.74 | 3.657 (2) | 163 |
C12—H12···O1i | 0.95 | 2.65 | 3.390 (2) | 135 |
C2—H2B···O1ii | 0.99 | 2.67 | 3.466 (2) | 138 |
C26—H26···O1ii | 0.95 | 2.70 | 3.431 (2) | 134 |
C22—H22···Cgiii | 0.95 | 2.81 | 3.721 (3) | 162 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x, −y, z−1/2; (iii) −x+1/2, −y+1/2, −z+1. |
Acknowledgements
AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young Scientist award.
References
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Isoxazoles are well known organic compounds which are included in a variety of complex biologically active structures and play a role as catalyst, ligands and intermediates for functional compounds (Miller et al., 2009; Prasad et al., 2007). Isoxazoles appear in numerous medicinally active compounds and natural products of biological significance. Additionally, they are valuable as synthetic intermediates or protecting groups in organic synthesis. Also, isoxazoles serve as monomers for the synthesis of substituted poly(imine)s by cationic ring-opening polymerization (Wiesbrock et al., 2005). Due to our interest in developing new isoxazole-based heterocycles, we have synthesized the title compound to study its crystal structure.
The title molecule features a chlorinated as well as a non-halogenated phenyl group as substituents on a central isoxazole core. The latter one adopts a 5E conformation with the flap atom on C3 (Cremer & Pople, 1975). While the halogenated phenyl group is nearly in-plane with the isoxazoline moiety – the least-squares planes defined by the respective intracyclic atoms intersect at an angle of 7.16 (7) ° only – the non-substituted phenyl group adopts a nearly perpendicular orientation towards the isoxazole moiety. The corresponding least-squares planes in the latter case enclose an angle of 74.93 (7) ° (Fig. 1).
In the crystal, only weak C–H···O and C–H···N contacts whose range falls slightly below the sum of van-der-Waals radii of the atoms participating in them are observed. The hydrogen atom that is part of the C–H···N contact stems from the chlorinated phenyl substituent and is also the origin of a bifuracated hydrogen bond that extends to the oxygen atom as acceptor. The C–H···O contacts are supported by the intracyclic methylene group as well as a hydrogen atom on the non-substituted phenyl group. Taking into account the latter two findings, the oxygen atom acts as threefold acceptor. Metrical parameters as well as information about the symmetry codes for these contacts are summarized in Table 1. In total, the molecules are connected to layers perpendicular to the crystallographic a axis. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for these contacts is C11(4)C11(5)C11(5)C11(6) on the unary level. The shortest intercentroid distance between two aromatic systems was measured at 4.709 (3) Å and is observed between the halogenated phenyl group and its symmetry-generated equivalent (Fig. 2).
The packing of the title compound in the crystal structure is shown in Figure 3.