Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680100109X/ci6003sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680100109X/ci6003Isup2.hkl |
CCDC reference: 159724
Triethylorthoformate (3.32 ml, 20 mmol) and acetic anhydride (3.57 ml, 38 mmol) were added to N-benzoylglycine (3.580 g, 20 mmol). The resulting reaction mixture was refluxed for 30 min and then kept in a freezer overnight. The precipitate of 4-(ethoxymethylene)-2-phenyl-5-oxazolone was filtered and washed with petroleum ether and dried. Equimolar quantity of 4-(ethoxymethylene)-2-phenyl-5-oxazolone and p-toluidine were taken in 10 ml of ethanol and the reaction mixture was refluxed for 2 h. On cooling, the precipitate of the title compound was obtained, which was washed with petroleum ether and ethanol and then recrystallized with ethanol.
All but methyl group H atoms were located from the difference map and were included in the structure-factor calculations with isotropic displacement parameters equal to 1.1Ueq of their respective carrier atom, but their positional parameters were not refined (C—H distances are in the range 0.95–1.10 Å), whereas the methyl H atoms were geometrically fixed and ariding model was used for their refinement.
Data collection: CAD-4 Software (Enraf-Nonius, 1994); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97.
C17H14N2O2 | F(000) = 1168 |
Mr = 278.30 | Dx = 1.283 Mg m−3 |
Monoclinic, P21/a | Cu Kα radiation, λ = 1.54180 Å |
a = 19.457 (2) Å | Cell parameters from 25 reflections |
b = 6.442 (1) Å | θ = 25–35° |
c = 24.619 (1) Å | µ = 0.69 mm−1 |
β = 110.95 (8)° | T = 293 K |
V = 2882.1 (5) Å3 | Plate, green |
Z = 8 | 0.3 × 0.15 × 0.1 mm |
Enraf-Nonius CAD-4 diffractometer | 4460 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.014 |
Graphite monochromator | θmax = 68.0°, θmin = 3.9° |
ω–2θ scans | h = −22→21 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→7 |
Tmin = 0.977, Tmax = 0.999 | l = 0→29 |
5422 measured reflections | 2 standard reflections every 120 min |
5130 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0634P)2 + 0.9752P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
5130 reflections | Δρmax = 0.25 e Å−3 |
380 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0016 (1) |
C17H14N2O2 | V = 2882.1 (5) Å3 |
Mr = 278.30 | Z = 8 |
Monoclinic, P21/a | Cu Kα radiation |
a = 19.457 (2) Å | µ = 0.69 mm−1 |
b = 6.442 (1) Å | T = 293 K |
c = 24.619 (1) Å | 0.3 × 0.15 × 0.1 mm |
β = 110.95 (8)° |
Enraf-Nonius CAD-4 diffractometer | 4460 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.014 |
Tmin = 0.977, Tmax = 0.999 | 2 standard reflections every 120 min |
5422 measured reflections | intensity decay: none |
5130 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.25 e Å−3 |
5130 reflections | Δρmin = −0.17 e Å−3 |
380 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.43879 (6) | 0.27315 (18) | 0.38929 (5) | 0.0533 (3) | |
N3 | 0.47554 (7) | 0.6043 (2) | 0.40946 (6) | 0.0472 (3) | |
N7 | 0.61569 (8) | 0.7326 (2) | 0.49721 (6) | 0.0498 (4) | |
O5 | 0.53821 (9) | 0.0981 (2) | 0.44839 (8) | 0.0928 (6) | |
C2 | 0.42435 (9) | 0.4823 (3) | 0.37932 (7) | 0.0426 (4) | |
C4 | 0.53157 (9) | 0.4731 (3) | 0.44386 (7) | 0.0463 (4) | |
C5 | 0.50944 (10) | 0.2635 (3) | 0.43137 (9) | 0.0555 (4) | |
C6 | 0.59694 (9) | 0.5355 (3) | 0.48394 (7) | 0.0473 (4) | |
C8 | 0.68379 (9) | 0.8018 (3) | 0.53787 (7) | 0.0470 (4) | |
C9 | 0.68608 (10) | 0.9963 (3) | 0.56300 (8) | 0.0544 (4) | |
C10 | 0.75212 (11) | 1.0679 (3) | 0.60274 (8) | 0.0615 (5) | |
C11 | 0.81564 (11) | 0.9500 (4) | 0.61962 (8) | 0.0654 (6) | |
C12 | 0.81179 (10) | 0.7566 (4) | 0.59401 (9) | 0.0678 (6) | |
C13 | 0.74677 (10) | 0.6835 (3) | 0.55276 (8) | 0.0568 (5) | |
C14 | 0.88665 (13) | 1.0293 (5) | 0.66413 (11) | 0.1000 (9) | |
H14A | 0.8787 | 1.1648 | 0.6770 | 0.150* | |
H14B | 0.9237 | 1.0371 | 0.6469 | 0.150* | |
H14C | 0.9026 | 0.9363 | 0.6967 | 0.150* | |
C15 | 0.35400 (9) | 0.5370 (3) | 0.33492 (7) | 0.0431 (4) | |
C16 | 0.29725 (10) | 0.3927 (3) | 0.31555 (7) | 0.0528 (4) | |
C17 | 0.23185 (10) | 0.4470 (3) | 0.27260 (8) | 0.0631 (5) | |
C18 | 0.22251 (10) | 0.6428 (4) | 0.24812 (8) | 0.0626 (5) | |
C19 | 0.27832 (11) | 0.7864 (3) | 0.26766 (8) | 0.0609 (5) | |
C20 | 0.34405 (10) | 0.7358 (3) | 0.31125 (8) | 0.0522 (4) | |
H6 | 0.6355 | 0.4279 | 0.5070 | 0.051* | |
H7 | 0.5814 | 0.8343 | 0.4755 | 0.052* | |
H9 | 0.6374 | 1.0882 | 0.5532 | 0.059* | |
H10 | 0.7482 | 1.2030 | 0.6221 | 0.065* | |
H12 | 0.8530 | 0.6650 | 0.6030 | 0.074* | |
H13 | 0.7467 | 0.5579 | 0.5328 | 0.061* | |
H16 | 0.3034 | 0.2459 | 0.3329 | 0.059* | |
H17 | 0.1936 | 0.3480 | 0.2574 | 0.066* | |
H18 | 0.1781 | 0.6799 | 0.2179 | 0.068* | |
H19 | 0.2718 | 0.9312 | 0.2490 | 0.066* | |
H20 | 0.3852 | 0.8373 | 0.3265 | 0.055* | |
O1A | 0.57198 (6) | 0.49562 (18) | 0.14322 (5) | 0.0500 (3) | |
N3A | 0.60747 (7) | 0.1633 (2) | 0.14250 (6) | 0.0427 (3) | |
O5A | 0.64575 (8) | 0.6621 (2) | 0.10399 (7) | 0.0711 (4) | |
N7A | 0.72455 (7) | 0.0257 (2) | 0.10218 (6) | 0.0461 (3) | |
C2A | 0.56458 (8) | 0.2891 (2) | 0.15540 (7) | 0.0405 (3) | |
C4A | 0.64991 (8) | 0.2894 (2) | 0.12023 (7) | 0.0416 (4) | |
C5A | 0.62771 (9) | 0.4999 (3) | 0.12003 (8) | 0.0480 (4) | |
C6A | 0.70500 (9) | 0.2223 (3) | 0.10212 (7) | 0.0427 (4) | |
C8A | 0.78082 (8) | −0.0529 (3) | 0.08402 (7) | 0.0434 (4) | |
C9A | 0.80931 (9) | −0.2478 (3) | 0.10414 (8) | 0.0522 (4) | |
C10A | 0.86373 (10) | −0.3329 (3) | 0.08697 (9) | 0.0608 (5) | |
C11A | 0.89198 (10) | −0.2252 (4) | 0.05074 (8) | 0.0612 (5) | |
C12A | 0.86336 (10) | −0.0308 (4) | 0.03175 (8) | 0.0609 (5) | |
C13A | 0.80754 (10) | 0.0554 (3) | 0.04723 (7) | 0.0507 (4) | |
C14A | 0.95183 (12) | −0.3198 (5) | 0.03262 (11) | 0.0915 (9) | |
H14D | 0.9644 | −0.4545 | 0.0500 | 0.137* | |
H14E | 0.9945 | −0.2321 | 0.0454 | 0.137* | |
H14F | 0.9344 | −0.3326 | −0.0090 | 0.137* | |
C15A | 0.51220 (8) | 0.2426 (3) | 0.18397 (7) | 0.0427 (4) | |
C16A | 0.46261 (10) | 0.3918 (3) | 0.18790 (8) | 0.0524 (4) | |
C17A | 0.41542 (11) | 0.3463 (4) | 0.21708 (9) | 0.0632 (5) | |
C18A | 0.41809 (12) | 0.1549 (4) | 0.24253 (10) | 0.0688 (6) | |
C19A | 0.46700 (12) | 0.0060 (4) | 0.23851 (10) | 0.0718 (6) | |
C20A | 0.51375 (10) | 0.0482 (3) | 0.20875 (9) | 0.0588 (5) | |
H6A | 0.7332 | 0.3311 | 0.0859 | 0.046* | |
H7A | 0.6982 | −0.0700 | 0.1141 | 0.048* | |
H9A | 0.7898 | −0.3257 | 0.1320 | 0.057* | |
H10A | 0.8827 | −0.4897 | 0.1033 | 0.064* | |
H12A | 0.8796 | 0.0501 | 0.0040 | 0.064* | |
H13A | 0.7865 | 0.1914 | 0.0316 | 0.054* | |
H16A | 0.4625 | 0.5225 | 0.1671 | 0.055* | |
H17A | 0.3792 | 0.4513 | 0.2207 | 0.067* | |
H18A | 0.3895 | 0.1297 | 0.2684 | 0.076* | |
H19A | 0.4711 | −0.1392 | 0.2592 | 0.079* | |
H20A | 0.5552 | −0.0599 | 0.2097 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0498 (7) | 0.0391 (7) | 0.0635 (7) | −0.0022 (5) | 0.0111 (6) | 0.0029 (5) |
N3 | 0.0454 (7) | 0.0418 (8) | 0.0493 (7) | 0.0008 (6) | 0.0110 (6) | 0.0006 (6) |
N7 | 0.0478 (8) | 0.0423 (8) | 0.0512 (8) | 0.0025 (6) | 0.0077 (6) | 0.0030 (6) |
O5 | 0.0759 (10) | 0.0421 (8) | 0.1279 (14) | 0.0080 (7) | −0.0030 (9) | 0.0145 (9) |
C2 | 0.0454 (8) | 0.0388 (9) | 0.0453 (8) | 0.0000 (7) | 0.0184 (7) | 0.0021 (7) |
C4 | 0.0448 (9) | 0.0413 (9) | 0.0501 (9) | 0.0027 (7) | 0.0136 (7) | 0.0026 (7) |
C5 | 0.0495 (9) | 0.0448 (10) | 0.0650 (11) | 0.0030 (8) | 0.0119 (8) | 0.0069 (8) |
C6 | 0.0471 (9) | 0.0437 (10) | 0.0485 (9) | 0.0021 (7) | 0.0140 (7) | 0.0041 (7) |
C8 | 0.0466 (9) | 0.0515 (10) | 0.0419 (8) | −0.0029 (7) | 0.0145 (7) | 0.0038 (7) |
C9 | 0.0593 (10) | 0.0499 (10) | 0.0507 (9) | −0.0033 (9) | 0.0158 (8) | 0.0005 (8) |
C10 | 0.0688 (12) | 0.0664 (13) | 0.0497 (10) | −0.0152 (10) | 0.0215 (9) | −0.0089 (9) |
C11 | 0.0538 (11) | 0.0927 (16) | 0.0504 (10) | −0.0184 (11) | 0.0197 (8) | −0.0088 (10) |
C12 | 0.0463 (10) | 0.0906 (16) | 0.0669 (12) | 0.0029 (10) | 0.0209 (9) | −0.0002 (11) |
C13 | 0.0513 (10) | 0.0618 (12) | 0.0586 (10) | −0.0003 (9) | 0.0213 (8) | −0.0047 (9) |
C14 | 0.0663 (14) | 0.153 (3) | 0.0730 (14) | −0.0285 (16) | 0.0158 (12) | −0.0309 (17) |
C15 | 0.0433 (8) | 0.0471 (9) | 0.0408 (8) | −0.0010 (7) | 0.0174 (7) | 0.0002 (7) |
C16 | 0.0534 (10) | 0.0535 (11) | 0.0488 (9) | −0.0080 (8) | 0.0149 (8) | 0.0028 (8) |
C17 | 0.0530 (10) | 0.0726 (14) | 0.0547 (10) | −0.0159 (10) | 0.0084 (8) | 0.0027 (10) |
C18 | 0.0505 (10) | 0.0799 (14) | 0.0492 (10) | 0.0006 (10) | 0.0077 (8) | 0.0095 (10) |
C19 | 0.0590 (11) | 0.0614 (12) | 0.0573 (10) | 0.0032 (9) | 0.0146 (9) | 0.0147 (9) |
C20 | 0.0484 (9) | 0.0511 (10) | 0.0544 (10) | −0.0038 (8) | 0.0149 (8) | 0.0050 (8) |
O1A | 0.0560 (7) | 0.0365 (6) | 0.0704 (7) | 0.0010 (5) | 0.0386 (6) | −0.0010 (5) |
N3A | 0.0426 (7) | 0.0401 (7) | 0.0496 (7) | 0.0020 (6) | 0.0215 (6) | 0.0020 (6) |
O5A | 0.0869 (10) | 0.0373 (7) | 0.1162 (12) | −0.0080 (7) | 0.0692 (9) | −0.0027 (7) |
N7A | 0.0466 (7) | 0.0385 (8) | 0.0617 (8) | 0.0011 (6) | 0.0297 (6) | 0.0013 (6) |
C2A | 0.0395 (8) | 0.0386 (8) | 0.0443 (8) | −0.0003 (7) | 0.0162 (6) | 0.0006 (7) |
C4A | 0.0414 (8) | 0.0377 (8) | 0.0495 (8) | −0.0012 (7) | 0.0208 (7) | −0.0019 (7) |
C5A | 0.0507 (9) | 0.0397 (9) | 0.0634 (10) | −0.0034 (7) | 0.0323 (8) | −0.0051 (8) |
C6A | 0.0428 (8) | 0.0382 (9) | 0.0507 (9) | −0.0013 (7) | 0.0209 (7) | −0.0030 (7) |
C8A | 0.0381 (8) | 0.0436 (9) | 0.0495 (8) | 0.0025 (7) | 0.0170 (7) | −0.0056 (7) |
C9A | 0.0469 (9) | 0.0452 (10) | 0.0644 (11) | 0.0041 (8) | 0.0199 (8) | −0.0021 (8) |
C10A | 0.0489 (10) | 0.0573 (12) | 0.0694 (12) | 0.0128 (9) | 0.0126 (9) | −0.0103 (9) |
C11A | 0.0427 (9) | 0.0818 (15) | 0.0548 (10) | 0.0127 (9) | 0.0121 (8) | −0.0186 (10) |
C12A | 0.0551 (10) | 0.0808 (14) | 0.0539 (10) | 0.0039 (10) | 0.0280 (9) | −0.0061 (10) |
C13A | 0.0528 (9) | 0.0532 (11) | 0.0506 (9) | 0.0065 (8) | 0.0237 (8) | 0.0000 (8) |
C14A | 0.0584 (12) | 0.129 (2) | 0.0864 (16) | 0.0292 (14) | 0.0256 (11) | −0.0273 (16) |
C15A | 0.0384 (8) | 0.0486 (9) | 0.0424 (8) | −0.0008 (7) | 0.0161 (6) | 0.0007 (7) |
C16A | 0.0543 (10) | 0.0563 (11) | 0.0530 (9) | 0.0098 (8) | 0.0269 (8) | 0.0094 (8) |
C17A | 0.0606 (11) | 0.0735 (14) | 0.0685 (12) | 0.0131 (10) | 0.0389 (10) | 0.0090 (10) |
C18A | 0.0704 (13) | 0.0771 (15) | 0.0763 (13) | −0.0009 (11) | 0.0477 (11) | 0.0089 (11) |
C19A | 0.0799 (14) | 0.0634 (13) | 0.0892 (15) | 0.0005 (11) | 0.0511 (13) | 0.0163 (11) |
C20A | 0.0570 (10) | 0.0536 (11) | 0.0744 (12) | 0.0034 (9) | 0.0339 (9) | 0.0110 (9) |
O1—C2 | 1.380 (2) | O1A—C2A | 1.383 (2) |
O1—C5 | 1.396 (2) | O1A—C5A | 1.3947 (19) |
N3—C2 | 1.277 (2) | N3A—C2A | 1.282 (2) |
N3—C4 | 1.400 (2) | N3A—C4A | 1.402 (2) |
N7—C6 | 1.329 (2) | O5A—C5A | 1.212 (2) |
N7—C8 | 1.417 (2) | N7A—C6A | 1.322 (2) |
N7—H7 | 0.9512 | N7A—C8A | 1.416 (2) |
O5—C5 | 1.206 (2) | N7A—H7A | 0.9147 |
C2—C15 | 1.457 (2) | C2A—C15A | 1.462 (2) |
C4—C6 | 1.362 (2) | C4A—C6A | 1.370 (2) |
C4—C5 | 1.418 (3) | C4A—C5A | 1.423 (2) |
C6—H6 | 1.0301 | C6A—H6A | 1.0529 |
C8—C13 | 1.377 (3) | C8A—C13A | 1.384 (2) |
C8—C9 | 1.391 (3) | C8A—C9A | 1.390 (2) |
C9—C10 | 1.386 (3) | C9A—C10A | 1.386 (2) |
C9—H9 | 1.0689 | C9A—H9A | 1.0259 |
C10—C11 | 1.382 (3) | C10A—C11A | 1.389 (3) |
C10—H10 | 1.008 | C10A—H10A | 1.101 |
C11—C12 | 1.386 (3) | C11A—C12A | 1.382 (3) |
C11—C14 | 1.513 (3) | C11A—C14A | 1.516 (3) |
C12—C13 | 1.391 (3) | C12A—C13A | 1.389 (2) |
C12—H12 | 0.956 | C12A—H12A | 0.996 |
C13—H13 | 0.946 | C13A—H13A | 0.9855 |
C14—H14A | 0.9600 | C14A—H14D | 0.9600 |
C14—H14B | 0.9600 | C14A—H14E | 0.9600 |
C14—H14C | 0.9600 | C14A—H14F | 0.9600 |
C15—C16 | 1.391 (2) | C15A—C20A | 1.389 (3) |
C15—C20 | 1.392 (2) | C15A—C16A | 1.389 (2) |
C16—C17 | 1.377 (3) | C16A—C17A | 1.385 (2) |
C16—H16 | 1.0268 | C16A—H16A | 0.9851 |
C17—C18 | 1.382 (3) | C17A—C18A | 1.376 (3) |
C17—H17 | 0.9494 | C17A—H17A | 1.0035 |
C18—C19 | 1.376 (3) | C18A—C19A | 1.379 (3) |
C18—H18 | 0.9474 | C18A—H18A | 0.9974 |
C19—C20 | 1.383 (2) | C19A—C20A | 1.384 (3) |
C19—H19 | 1.028 | C19A—H19A | 1.054 |
C20—H20 | 0.9972 | C20A—H20A | 1.0595 |
C2—O1—C5 | 105.04 (13) | C2A—O1A—C5A | 105.33 (12) |
C2—N3—C4 | 104.90 (14) | C2A—N3A—C4A | 104.89 (13) |
C6—N7—C8 | 125.39 (14) | C6A—N7A—C8A | 126.65 (14) |
C6—N7—H7 | 116.36 | C6A—N7A—H7A | 116.86 |
C8—N7—H7 | 118.11 | C8A—N7A—H7A | 116.47 |
N3—C2—O1 | 115.49 (14) | N3A—C2A—O1A | 115.29 (13) |
N3—C2—C15 | 127.97 (16) | N3A—C2A—C15A | 128.13 (15) |
O1—C2—C15 | 116.52 (14) | O1A—C2A—C15A | 116.50 (13) |
C6—C4—N3 | 125.73 (16) | C6A—C4A—N3A | 125.66 (15) |
C6—C4—C5 | 124.79 (16) | C6A—C4A—C5A | 124.88 (15) |
N3—C4—C5 | 109.47 (14) | N3A—C4A—C5A | 109.46 (13) |
O5—C5—O1 | 120.59 (17) | O5A—C5A—O1A | 120.56 (15) |
O5—C5—C4 | 134.31 (17) | O5A—C5A—C4A | 134.40 (15) |
O1—C5—C4 | 105.10 (14) | O1A—C5A—C4A | 105.02 (13) |
N7—C6—C4 | 124.25 (16) | N7A—C6A—C4A | 124.09 (15) |
N7—C6—H6 | 115.20 | N7A—C6A—H6A | 116.70 |
C4—C6—H6 | 120.54 | C4A—C6A—H6A | 119.19 |
C13—C8—C9 | 119.76 (17) | C13A—C8A—C9A | 119.56 (15) |
C13—C8—N7 | 122.15 (17) | C13A—C8A—N7A | 122.71 (15) |
C9—C8—N7 | 118.09 (16) | C9A—C8A—N7A | 117.73 (15) |
C10—C9—C8 | 119.20 (18) | C10A—C9A—C8A | 119.95 (18) |
C10—C9—H9 | 119.87 | C10A—C9A—H9A | 121.08 |
C8—C9—H9 | 120.90 | C8A—C9A—H9A | 118.97 |
C11—C10—C9 | 122.2 (2) | C9A—C10A—C11A | 121.28 (18) |
C11—C10—H10 | 122.88 | C9A—C10A—H10A | 116.38 |
C9—C10—H10 | 114.4 | C11A—C10A—H10A | 122.34 |
C10—C11—C12 | 117.40 (18) | C12A—C11A—C10A | 117.76 (17) |
C10—C11—C14 | 121.3 (2) | C12A—C11A—C14A | 121.6 (2) |
C12—C11—C14 | 121.3 (2) | C10A—C11A—C14A | 120.7 (2) |
C11—C12—C13 | 121.56 (19) | C11A—C12A—C13A | 121.96 (18) |
C11—C12—H12 | 123.0 | C11A—C12A—H12A | 121.19 |
C13—C12—H12 | 115.4 | C13A—C12A—H12A | 116.7 |
C8—C13—C12 | 119.83 (19) | C8A—C13A—C12A | 119.47 (17) |
C8—C13—H13 | 119.95 | C8A—C13A—H13A | 120.20 |
C12—C13—H13 | 120.04 | C12A—C13A—H13A | 120.32 |
C11—C14—H14A | 109.5 | C11A—C14A—H14D | 109.5 |
C11—C14—H14B | 109.5 | C11A—C14A—H14E | 109.5 |
H14A—C14—H14B | 109.5 | H14D—C14A—H14E | 109.5 |
C11—C14—H14C | 109.5 | C11A—C14A—H14F | 109.5 |
H14A—C14—H14C | 109.5 | H14D—C14A—H14F | 109.5 |
H14B—C14—H14C | 109.5 | H14E—C14A—H14F | 109.5 |
C16—C15—C20 | 119.82 (16) | C20A—C15A—C16A | 120.00 (15) |
C16—C15—C2 | 120.87 (16) | C20A—C15A—C2A | 119.13 (15) |
C20—C15—C2 | 119.31 (15) | C16A—C15A—C2A | 120.85 (15) |
C17—C16—C15 | 119.71 (18) | C17A—C16A—C15A | 119.70 (17) |
C17—C16—H16 | 119.43 | C17A—C16A—H16A | 124.90 |
C15—C16—H16 | 120.86 | C15A—C16A—H16A | 115.31 |
C16—C17—C18 | 120.53 (18) | C18A—C17A—C16A | 120.14 (18) |
C16—C17—H17 | 120.7 | C18A—C17A—H17A | 118.51 |
C18—C17—H17 | 118.62 | C16A—C17A—H17A | 121.4 |
C19—C18—C17 | 119.81 (17) | C17A—C18A—C19A | 120.35 (17) |
C19—C18—H18 | 119.3 | C17A—C18A—H18A | 119.8 |
C17—C18—H18 | 120.9 | C19A—C18A—H18A | 119.3 |
C18—C19—C20 | 120.56 (18) | C18A—C19A—C20A | 120.16 (19) |
C18—C19—H19 | 119.89 | C18A—C19A—H19A | 121.14 |
C20—C19—H19 | 119.53 | C20A—C19A—H19A | 118.7 |
C19—C20—C15 | 119.56 (17) | C19A—C20A—C15A | 119.64 (18) |
C19—C20—H20 | 122.21 | C19A—C20A—H20A | 119.90 |
C15—C20—H20 | 118.23 | C15A—C20A—H20A | 119.97 |
C4—N3—C2—O1 | 0.18 (19) | C4A—N3A—C2A—O1A | 1.05 (18) |
C4—N3—C2—C15 | −177.98 (16) | C4A—N3A—C2A—C15A | −175.35 (15) |
C5—O1—C2—N3 | −0.6 (2) | C5A—O1A—C2A—N3A | −0.66 (19) |
C5—O1—C2—C15 | 177.81 (14) | C5A—O1A—C2A—C15A | 176.18 (13) |
C2—N3—C4—C6 | −178.72 (17) | C2A—N3A—C4A—C6A | 178.13 (16) |
C2—N3—C4—C5 | 0.29 (19) | C2A—N3A—C4A—C5A | −1.03 (18) |
C2—O1—C5—O5 | −178.5 (2) | C2A—O1A—C5A—O5A | 178.60 (17) |
C2—O1—C5—C4 | 0.68 (19) | C2A—O1A—C5A—C4A | −0.05 (18) |
C6—C4—C5—O5 | −2.6 (4) | C6A—C4A—C5A—O5A | 3.1 (3) |
N3—C4—C5—O5 | 178.4 (2) | N3A—C4A—C5A—O5A | −177.7 (2) |
C6—C4—C5—O1 | 178.40 (16) | C6A—C4A—C5A—O1A | −178.51 (15) |
N3—C4—C5—O1 | −0.6 (2) | N3A—C4A—C5A—O1A | 0.66 (19) |
C8—N7—C6—C4 | −178.7 (2) | C8A—N7A—C6A—C4A | 180.0 (2) |
N3—C4—C6—N7 | 2.1 (3) | N3A—C4A—C6A—N7A | 1.5 (3) |
C5—C4—C6—N7 | −176.73 (18) | C5A—C4A—C6A—N7A | −179.45 (17) |
C6—N7—C8—C13 | 23.7 (3) | C6A—N7A—C8A—C13A | −20.9 (3) |
C6—N7—C8—C9 | −156.48 (17) | C6A—N7A—C8A—C9A | 159.59 (17) |
C13—C8—C9—C10 | 0.1 (3) | C13A—C8A—C9A—C10A | −0.5 (3) |
N7—C8—C9—C10 | −179.75 (16) | N7A—C8A—C9A—C10A | 179.08 (16) |
C8—C9—C10—C11 | −1.9 (3) | C8A—C9A—C10A—C11A | 1.4 (3) |
C9—C10—C11—C12 | 1.7 (3) | C9A—C10A—C11A—C12A | −0.7 (3) |
C9—C10—C11—C14 | −178.5 (2) | C9A—C10A—C11A—C14A | 179.63 (18) |
C10—C11—C12—C13 | 0.2 (3) | C10A—C11A—C12A—C13A | −0.9 (3) |
C14—C11—C12—C13 | −179.6 (2) | C14A—C11A—C12A—C13A | 178.74 (19) |
C9—C8—C13—C12 | 1.8 (3) | C9A—C8A—C13A—C12A | −1.1 (3) |
N7—C8—C13—C12 | −178.41 (17) | N7A—C8A—C13A—C12A | 179.36 (16) |
C11—C12—C13—C8 | −1.9 (3) | C11A—C12A—C13A—C8A | 1.8 (3) |
N3—C2—C15—C16 | −164.89 (17) | N3A—C2A—C15A—C20A | 10.4 (3) |
O1—C2—C15—C16 | 17.0 (2) | O1A—C2A—C15A—C20A | −165.94 (16) |
N3—C2—C15—C20 | 15.9 (3) | N3A—C2A—C15A—C16A | −171.31 (16) |
O1—C2—C15—C20 | −162.28 (15) | O1A—C2A—C15A—C16A | 12.3 (2) |
C20—C15—C16—C17 | 0.7 (3) | C20A—C15A—C16A—C17A | 0.6 (3) |
C2—C15—C16—C17 | −178.54 (17) | C2A—C15A—C16A—C17A | −177.60 (17) |
C15—C16—C17—C18 | 0.8 (3) | C15A—C16A—C17A—C18A | 0.6 (3) |
C16—C17—C18—C19 | −1.4 (3) | C16A—C17A—C18A—C19A | −0.9 (3) |
C17—C18—C19—C20 | 0.6 (3) | C17A—C18A—C19A—C20A | 0.0 (4) |
C18—C19—C20—C15 | 0.9 (3) | C18A—C19A—C20A—C15A | 1.3 (3) |
C16—C15—C20—C19 | −1.5 (3) | C16A—C15A—C20A—C19A | −1.6 (3) |
C2—C15—C20—C19 | 177.73 (16) | C2A—C15A—C20A—C19A | 176.70 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7···O5i | 0.95 | 1.91 | 2.822 (2) | 161 |
N7A—H7A···O5Aii | 0.92 | 1.98 | 2.809 (2) | 151 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C17H14N2O2 |
Mr | 278.30 |
Crystal system, space group | Monoclinic, P21/a |
Temperature (K) | 293 |
a, b, c (Å) | 19.457 (2), 6.442 (1), 24.619 (1) |
β (°) | 110.95 (8) |
V (Å3) | 2882.1 (5) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 0.69 |
Crystal size (mm) | 0.3 × 0.15 × 0.1 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.977, 0.999 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5422, 5130, 4460 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.125, 1.06 |
No. of reflections | 5130 |
No. of parameters | 380 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.17 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1994), CAD-4 Software, MolEN (Fair, 1990), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997), SHELXL97.
N3—C2 | 1.277 (2) | N3A—C2A | 1.282 (2) |
N3—C4 | 1.400 (2) | N3A—C4A | 1.402 (2) |
N7—C8 | 1.417 (2) | N7A—C8A | 1.416 (2) |
C4—C6 | 1.362 (2) | C4A—C6A | 1.370 (2) |
C8—N7—C6—C4 | −178.7 (2) | C8A—N7A—C6A—C4A | 180.0 (2) |
C6—N7—C8—C13 | 23.7 (3) | C6A—N7A—C8A—C13A | −20.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7···O5i | 0.95 | 1.91 | 2.822 (2) | 161 |
N7A—H7A···O5Aii | 0.92 | 1.98 | 2.809 (2) | 151 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z. |
The structure determination of the title compound, (I), was undertaken to study the effect of substitutions at 2 and 4 positions on the oxazoline ring and the nature of hydrogen bonding. There are two crystallographically independent molecules in the asymmetric unit, Molecules I and II (atoms are labelled with addition letter A to the corresponding atoms of molecule II). The planarity of the oxazoline ring is not affected by the substitutions on the 2 and 4 positions. The dihedral angle between the phenyl ring and the oxazoline ring is 17.29 (10)° [13.35 (10)°]. The dihedral angle between the oxazoline ring and the toluidino moiety is 26.68 (10)° [19.10 (9)°]. The N7—C6 bond {1.329 (2) Å [1.322 (2) Å]} shows a partial double-bond character. This may be due to the delocalization of the lone pair of electrons of the N atom over the N7—C6═C4 moiety (Thiruvalluvar et al., 1995). The exocyclic bond angles N3—C2—C15 and N3A–C2A—C15A are 128.0 (2) and 128.1 (2)°, respectively. This increase from the normal 120° may be the consequence of the repulsion between the lone pair of electrons of the N and the H atom of C20 and C20A (Vijayalakshmi et al., 1998). In the crystal, the N—H group of the molecules are involved in N—H···O type intermolecular hydrogen bonds (Table 2).