Acta Cryst. (2008). E64, o2315 [ doi:10.1107/S1600536808035988 ]
In the title compound, C20H19NO5, the dihydrofuran ring is almost planar [maximum deviation of 0.021 (2)°] and makes dihedral angles of 28.1 (7) and 54.5 (5)° with the benzyl and phenylamino rings, respectively. The molecular packing is stabilized by intramolecular N-H
O hydrogen bonds and intermolecular C-HO interactions.
1.0 mol of 4-(benzyloxy) aniline (1.0 g) and 1.0 mol of ethyl 2-chloro-4- oxo-4,5-dihydrofuran-3-carboxylate (0.9 g) was allowed to stir in 10 ml of dichloromethane which contains 0.5 ml of triethylamine at room temperature for about 8 hrs. The completion of the reaction was monitored by TLC. After the completion of reaction the crude solid was filtered and then recrystallized in ethanol.
H atoms were positioned geometrically and were treated as riding on their parent C atoms, with aromatic C—H distances of 0.93 Å, methyl C—H distances of 0.96 Å and methylene C—H distances of 0.97 Å, and with Uiso(H) = 1.5Ueq(C) for methyl H and 1.2Ueq(C) for other H atoms.
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
![[Figure 1]](./bq2103fig1thm.gif)
| Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids. Dashed line indicates hydrogen bond. |
![[Figure 2]](./bq2103fig2thm.gif)
| Fig. 2. The packing of the molecules viewed down the c axis. Dashed lines indicate hydrogen bonds. H atoms not involed in hydrogen bonds have been omitted. |
| C20H19NO5 | Z = 2 |
| Mr = 353.36 | F(000) = 372 |
| Triclinic, P1 | Dx = 1.355 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 9.1315 (3) Å | Cell parameters from 6361 reflections |
| b = 10.4040 (3) Å | θ = 2.6–30.7° |
| c = 11.1162 (4) Å | µ = 0.10 mm−1 |
| α = 84.848 (2)° | T = 293 K |
| β = 66.436 (2)° | Prism, yellow |
| γ = 64.121 (2)° | 0.25 × 0.20 × 0.20 mm |
| V = 866.34 (5) Å3 |
| Bruker Kappa APEXII diffractometer | 5349 independent reflections |
| Radiation source: fine-focus sealed tube | 3665 reflections with I > 2σ(I) |
| graphite | Rint = 0.025 |
| Bruker axs (kappa apex2) scans | θmax = 30.7°, θmin = 2.0° |
| Absorption correction: multi-scan (Blessing, 1995) | h = −13→13 |
| Tmin = 0.976, Tmax = 0.981 | k = −14→14 |
| 22596 measured reflections | l = −15→15 |
| 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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.163 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0812P)2 + 0.1488P] where P = (Fo2 + 2Fc2)/3 |
| 5349 reflections | (Δ/σ)max < 0.001 |
| 235 parameters | Δρmax = 0.29 e Å−3 |
| 0 restraints | Δρmin = −0.20 e Å−3 |
| C20H19NO5 | γ = 64.121 (2)° |
| Mr = 353.36 | V = 866.34 (5) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 9.1315 (3) Å | Mo Kα radiation |
| b = 10.4040 (3) Å | µ = 0.10 mm−1 |
| c = 11.1162 (4) Å | T = 293 K |
| α = 84.848 (2)° | 0.25 × 0.20 × 0.20 mm |
| β = 66.436 (2)° |
| Bruker Kappa APEXII diffractometer | 3665 reflections with I > 2σ(I) |
| Absorption correction: multi-scan (Blessing, 1995) | Rint = 0.025 |
| Tmin = 0.976, Tmax = 0.981 | θmax = 30.7° |
| 22596 measured reflections | Standard reflections: 0 |
| 5349 independent reflections |
| R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
| wR(F2) = 0.163 | Δρmax = 0.29 e Å−3 |
| S = 1.03 | Δρmin = −0.20 e Å−3 |
| 5349 reflections | Absolute structure: ? |
| 235 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| C1 | 1.26357 (19) | 0.57501 (15) | 0.0775 (2) | 0.0570 (4) | |
| H1A | 1.3252 | 0.5714 | 0.1323 | 0.068* | |
| H1B | 1.3224 | 0.6003 | −0.0086 | 0.068* | |
| C2 | 1.26228 (18) | 0.43137 (14) | 0.06491 (15) | 0.0437 (3) | |
| C3 | 1.07887 (17) | 0.46034 (12) | 0.12356 (14) | 0.0386 (3) | |
| C4 | 0.98080 (17) | 0.60818 (13) | 0.15886 (14) | 0.0396 (3) | |
| C5 | 0.71086 (17) | 0.83503 (13) | 0.24252 (14) | 0.0421 (3) | |
| C6 | 0.58376 (19) | 0.91391 (14) | 0.19371 (16) | 0.0496 (3) | |
| H6 | 0.5628 | 0.8684 | 0.1383 | 0.060* | |
| C7 | 0.4878 (2) | 1.06059 (15) | 0.22738 (17) | 0.0517 (4) | |
| H7 | 0.4011 | 1.1138 | 0.1956 | 0.062* | |
| C8 | 0.52074 (18) | 1.12851 (14) | 0.30861 (15) | 0.0447 (3) | |
| C9 | 0.6476 (2) | 1.04905 (15) | 0.35756 (16) | 0.0515 (4) | |
| H9 | 0.6699 | 1.0941 | 0.4122 | 0.062* | |
| C10 | 0.7412 (2) | 0.90186 (15) | 0.32472 (16) | 0.0513 (4) | |
| H10 | 0.8253 | 0.8479 | 0.3587 | 0.062* | |
| C11 | 0.4551 (2) | 1.34824 (16) | 0.41338 (19) | 0.0572 (4) | |
| H11A | 0.5762 | 1.3371 | 0.3698 | 0.069* | |
| H11B | 0.4396 | 1.3104 | 0.4983 | 0.069* | |
| C12 | 0.3260 (2) | 1.50396 (14) | 0.43163 (15) | 0.0464 (3) | |
| C13 | 0.1520 (2) | 1.54983 (19) | 0.51716 (18) | 0.0639 (4) | |
| H13 | 0.1136 | 1.4836 | 0.5635 | 0.077* | |
| C14 | 0.0329 (3) | 1.6920 (2) | 0.5359 (2) | 0.0798 (6) | |
| H14 | −0.0853 | 1.7216 | 0.5940 | 0.096* | |
| C15 | 0.0884 (3) | 1.78924 (19) | 0.4692 (3) | 0.0816 (7) | |
| H15 | 0.0083 | 1.8858 | 0.4818 | 0.098* | |
| C16 | 0.2604 (4) | 1.7455 (2) | 0.3842 (3) | 0.0888 (7) | |
| H16 | 0.2983 | 1.8124 | 0.3390 | 0.107* | |
| C17 | 0.3794 (3) | 1.6028 (2) | 0.3642 (2) | 0.0678 (5) | |
| H17 | 0.4968 | 1.5734 | 0.3045 | 0.081* | |
| C18 | 0.99189 (18) | 0.36906 (13) | 0.14162 (14) | 0.0416 (3) | |
| C19 | 1.0226 (3) | 0.13250 (17) | 0.1330 (3) | 0.0729 (6) | |
| H19A | 0.9252 | 0.1571 | 0.2193 | 0.088* | |
| H19B | 0.9755 | 0.1409 | 0.0669 | 0.088* | |
| C20 | 1.1542 (3) | −0.01258 (19) | 0.1230 (3) | 0.0969 (8) | |
| H20A | 1.1010 | −0.0772 | 0.1362 | 0.145* | |
| H20B | 1.1996 | −0.0205 | 0.1892 | 0.145* | |
| H20C | 1.2498 | −0.0367 | 0.0372 | 0.145* | |
| N1 | 0.80732 (15) | 0.68332 (11) | 0.20754 (13) | 0.0465 (3) | |
| H1 | 0.7456 | 0.6366 | 0.2196 | 0.056* | |
| O1 | 0.42051 (15) | 1.27356 (10) | 0.33465 (12) | 0.0582 (3) | |
| O2 | 1.07889 (13) | 0.67841 (9) | 0.13778 (12) | 0.0516 (3) | |
| O3 | 1.39676 (13) | 0.32190 (11) | 0.01100 (13) | 0.0599 (3) | |
| O4 | 0.83217 (13) | 0.41370 (11) | 0.18030 (13) | 0.0568 (3) | |
| O5 | 1.10361 (13) | 0.22984 (10) | 0.11310 (12) | 0.0522 (3) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0359 (7) | 0.0384 (7) | 0.0945 (12) | −0.0144 (6) | −0.0230 (7) | −0.0096 (7) |
| C2 | 0.0369 (6) | 0.0328 (6) | 0.0618 (8) | −0.0125 (5) | −0.0221 (6) | −0.0017 (5) |
| C3 | 0.0350 (6) | 0.0269 (5) | 0.0514 (7) | −0.0118 (4) | −0.0164 (5) | 0.0010 (5) |
| C4 | 0.0365 (6) | 0.0293 (5) | 0.0512 (7) | −0.0138 (5) | −0.0161 (5) | 0.0010 (5) |
| C5 | 0.0329 (6) | 0.0283 (5) | 0.0550 (8) | −0.0099 (5) | −0.0111 (5) | −0.0017 (5) |
| C6 | 0.0440 (7) | 0.0350 (6) | 0.0669 (9) | −0.0108 (6) | −0.0241 (7) | −0.0080 (6) |
| C7 | 0.0477 (8) | 0.0345 (6) | 0.0683 (10) | −0.0062 (6) | −0.0297 (7) | −0.0062 (6) |
| C8 | 0.0396 (7) | 0.0313 (6) | 0.0531 (8) | −0.0074 (5) | −0.0159 (6) | −0.0064 (5) |
| C9 | 0.0499 (8) | 0.0383 (7) | 0.0627 (9) | −0.0108 (6) | −0.0261 (7) | −0.0081 (6) |
| C10 | 0.0473 (8) | 0.0365 (7) | 0.0638 (9) | −0.0073 (6) | −0.0275 (7) | −0.0013 (6) |
| C11 | 0.0551 (9) | 0.0374 (7) | 0.0748 (11) | −0.0102 (6) | −0.0299 (8) | −0.0108 (7) |
| C12 | 0.0490 (8) | 0.0342 (6) | 0.0518 (8) | −0.0126 (6) | −0.0204 (6) | −0.0068 (5) |
| C13 | 0.0594 (10) | 0.0494 (9) | 0.0610 (10) | −0.0147 (8) | −0.0135 (8) | 0.0040 (7) |
| C14 | 0.0601 (11) | 0.0616 (11) | 0.0776 (13) | 0.0030 (9) | −0.0178 (10) | −0.0184 (10) |
| C15 | 0.0951 (16) | 0.0345 (8) | 0.1246 (18) | −0.0077 (9) | −0.0732 (15) | −0.0061 (10) |
| C16 | 0.1034 (18) | 0.0548 (11) | 0.144 (2) | −0.0476 (12) | −0.0750 (17) | 0.0374 (12) |
| C17 | 0.0592 (10) | 0.0604 (10) | 0.0887 (13) | −0.0320 (9) | −0.0288 (10) | 0.0112 (9) |
| C18 | 0.0398 (7) | 0.0289 (5) | 0.0547 (8) | −0.0148 (5) | −0.0179 (6) | 0.0041 (5) |
| C19 | 0.0681 (11) | 0.0381 (8) | 0.1251 (17) | −0.0328 (8) | −0.0411 (11) | 0.0130 (9) |
| C20 | 0.0866 (15) | 0.0382 (9) | 0.163 (3) | −0.0326 (10) | −0.0444 (16) | 0.0207 (12) |
| N1 | 0.0357 (6) | 0.0280 (5) | 0.0686 (8) | −0.0124 (4) | −0.0146 (5) | −0.0015 (5) |
| O1 | 0.0597 (7) | 0.0308 (5) | 0.0779 (8) | −0.0033 (4) | −0.0362 (6) | −0.0140 (5) |
| O2 | 0.0383 (5) | 0.0299 (4) | 0.0823 (8) | −0.0144 (4) | −0.0185 (5) | −0.0058 (4) |
| O3 | 0.0359 (5) | 0.0388 (5) | 0.0931 (9) | −0.0083 (4) | −0.0198 (5) | −0.0128 (5) |
| O4 | 0.0388 (5) | 0.0388 (5) | 0.0878 (8) | −0.0184 (4) | −0.0185 (5) | 0.0037 (5) |
| O5 | 0.0450 (5) | 0.0266 (4) | 0.0821 (8) | −0.0160 (4) | −0.0215 (5) | 0.0018 (4) |
| C1—O2 | 1.4466 (17) | C11—H11A | 0.9700 |
| C1—C2 | 1.5190 (19) | C11—H11B | 0.9700 |
| C1—H1A | 0.9700 | C12—C17 | 1.365 (2) |
| C1—H1B | 0.9700 | C12—C13 | 1.367 (2) |
| C2—O3 | 1.2156 (16) | C13—C14 | 1.373 (2) |
| C2—C3 | 1.4291 (19) | C13—H13 | 0.9300 |
| C3—C4 | 1.3953 (16) | C14—C15 | 1.357 (3) |
| C3—C18 | 1.4386 (17) | C14—H14 | 0.9300 |
| C4—N1 | 1.3126 (17) | C15—C16 | 1.354 (4) |
| C4—O2 | 1.3281 (15) | C15—H15 | 0.9300 |
| C5—C10 | 1.371 (2) | C16—C17 | 1.376 (3) |
| C5—C6 | 1.381 (2) | C16—H16 | 0.9300 |
| C5—N1 | 1.4287 (15) | C17—H17 | 0.9300 |
| C6—C7 | 1.3820 (18) | C18—O4 | 1.2128 (17) |
| C6—H6 | 0.9300 | C18—O5 | 1.3316 (15) |
| C7—C8 | 1.387 (2) | C19—C20 | 1.441 (3) |
| C7—H7 | 0.9300 | C19—O5 | 1.4506 (17) |
| C8—O1 | 1.3637 (15) | C19—H19A | 0.9700 |
| C8—C9 | 1.381 (2) | C19—H19B | 0.9700 |
| C9—C10 | 1.3847 (19) | C20—H20A | 0.9600 |
| C9—H9 | 0.9300 | C20—H20B | 0.9600 |
| C10—H10 | 0.9300 | C20—H20C | 0.9600 |
| C11—O1 | 1.4238 (18) | N1—H1 | 0.8600 |
| C11—C12 | 1.5022 (19) | ||
| O2—C1—C2 | 105.83 (11) | C17—C12—C13 | 118.54 (15) |
| O2—C1—H1A | 110.6 | C17—C12—C11 | 121.00 (15) |
| C2—C1—H1A | 110.6 | C13—C12—C11 | 120.46 (15) |
| O2—C1—H1B | 110.6 | C12—C13—C14 | 121.09 (18) |
| C2—C1—H1B | 110.6 | C12—C13—H13 | 119.5 |
| H1A—C1—H1B | 108.7 | C14—C13—H13 | 119.5 |
| O3—C2—C3 | 131.81 (12) | C15—C14—C13 | 119.7 (2) |
| O3—C2—C1 | 122.98 (13) | C15—C14—H14 | 120.1 |
| C3—C2—C1 | 105.18 (11) | C13—C14—H14 | 120.1 |
| C4—C3—C2 | 106.96 (11) | C16—C15—C14 | 119.92 (17) |
| C4—C3—C18 | 121.03 (12) | C16—C15—H15 | 120.0 |
| C2—C3—C18 | 131.90 (11) | C14—C15—H15 | 120.0 |
| N1—C4—O2 | 117.79 (11) | C15—C16—C17 | 120.4 (2) |
| N1—C4—C3 | 127.88 (12) | C15—C16—H16 | 119.8 |
| O2—C4—C3 | 114.33 (11) | C17—C16—H16 | 119.8 |
| C10—C5—C6 | 120.12 (12) | C12—C17—C16 | 120.32 (19) |
| C10—C5—N1 | 120.95 (13) | C12—C17—H17 | 119.8 |
| C6—C5—N1 | 118.92 (13) | C16—C17—H17 | 119.8 |
| C5—C6—C7 | 119.82 (13) | O4—C18—O5 | 122.88 (12) |
| C5—C6—H6 | 120.1 | O4—C18—C3 | 123.59 (12) |
| C7—C6—H6 | 120.1 | O5—C18—C3 | 113.52 (11) |
| C6—C7—C8 | 120.03 (14) | C20—C19—O5 | 109.29 (15) |
| C6—C7—H7 | 120.0 | C20—C19—H19A | 109.8 |
| C8—C7—H7 | 120.0 | O5—C19—H19A | 109.8 |
| O1—C8—C9 | 124.60 (13) | C20—C19—H19B | 109.8 |
| O1—C8—C7 | 115.48 (13) | O5—C19—H19B | 109.8 |
| C9—C8—C7 | 119.92 (12) | H19A—C19—H19B | 108.3 |
| C8—C9—C10 | 119.57 (14) | C19—C20—H20A | 109.5 |
| C8—C9—H9 | 120.2 | C19—C20—H20B | 109.5 |
| C10—C9—H9 | 120.2 | H20A—C20—H20B | 109.5 |
| C5—C10—C9 | 120.52 (14) | C19—C20—H20C | 109.5 |
| C5—C10—H10 | 119.7 | H20A—C20—H20C | 109.5 |
| C9—C10—H10 | 119.7 | H20B—C20—H20C | 109.5 |
| O1—C11—C12 | 107.46 (12) | C4—N1—C5 | 126.48 (11) |
| O1—C11—H11A | 110.2 | C4—N1—H1 | 116.8 |
| C12—C11—H11A | 110.2 | C5—N1—H1 | 116.8 |
| O1—C11—H11B | 110.2 | C8—O1—C11 | 117.26 (12) |
| C12—C11—H11B | 110.2 | C4—O2—C1 | 107.56 (10) |
| H11A—C11—H11B | 108.5 | C18—O5—C19 | 115.87 (12) |
| O2—C1—C2—O3 | 175.75 (15) | C12—C13—C14—C15 | −0.4 (3) |
| O2—C1—C2—C3 | −2.44 (18) | C13—C14—C15—C16 | 0.3 (3) |
| O3—C2—C3—C4 | −174.22 (17) | C14—C15—C16—C17 | 0.4 (4) |
| C1—C2—C3—C4 | 3.74 (17) | C13—C12—C17—C16 | 1.0 (3) |
| O3—C2—C3—C18 | 1.9 (3) | C11—C12—C17—C16 | −178.56 (18) |
| C1—C2—C3—C18 | 179.84 (16) | C15—C16—C17—C12 | −1.1 (3) |
| C2—C3—C4—N1 | 174.99 (15) | C4—C3—C18—O4 | 4.4 (2) |
| C18—C3—C4—N1 | −1.6 (2) | C2—C3—C18—O4 | −171.19 (16) |
| C2—C3—C4—O2 | −4.03 (17) | C4—C3—C18—O5 | −174.86 (13) |
| C18—C3—C4—O2 | 179.36 (13) | C2—C3—C18—O5 | 9.5 (2) |
| C10—C5—C6—C7 | 0.3 (2) | O2—C4—N1—C5 | −0.9 (2) |
| N1—C5—C6—C7 | 179.38 (14) | C3—C4—N1—C5 | −179.88 (14) |
| C5—C6—C7—C8 | 0.8 (2) | C10—C5—N1—C4 | −52.3 (2) |
| C6—C7—C8—O1 | 179.24 (15) | C6—C5—N1—C4 | 128.62 (17) |
| C6—C7—C8—C9 | −1.1 (2) | C9—C8—O1—C11 | 2.8 (2) |
| O1—C8—C9—C10 | 179.81 (15) | C7—C8—O1—C11 | −177.55 (15) |
| C7—C8—C9—C10 | 0.1 (3) | C12—C11—O1—C8 | −178.33 (13) |
| C6—C5—C10—C9 | −1.3 (2) | N1—C4—O2—C1 | −176.74 (14) |
| N1—C5—C10—C9 | 179.71 (14) | C3—C4—O2—C1 | 2.39 (18) |
| C8—C9—C10—C5 | 1.0 (3) | C2—C1—O2—C4 | 0.15 (18) |
| O1—C11—C12—C17 | −104.90 (19) | O4—C18—O5—C19 | −0.9 (2) |
| O1—C11—C12—C13 | 75.5 (2) | C3—C18—O5—C19 | 178.40 (16) |
| C17—C12—C13—C14 | −0.3 (3) | C20—C19—O5—C18 | −168.96 (18) |
| C11—C12—C13—C14 | 179.31 (17) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O4 | 0.86 | 2.12 | 2.7485 (15) | 129 |
| C6—H6···O3i | 0.93 | 2.51 | 3.3951 (18) | 160 |
| C17—H17···O4ii | 0.93 | 2.58 | 3.465 (2) | 160 |
| Symmetry codes: (i) −x+2, −y+1, −z; (ii) x, y+1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O4 | 0.86 | 2.12 | 2.7485 (15) | 129 |
| C6—H6···O3i | 0.93 | 2.51 | 3.3951 (18) | 160 |
| C17—H17···O4ii | 0.93 | 2.58 | 3.465 (2) | 160 |
| Symmetry codes: (i) −x+2, −y+1, −z; (ii) x, y+1, z. |
SN thanks Professor M. N. Ponnuswamy, Department of Crystallography and Biophysics, University of Madras, India, for his guidance and valuable suggestions. SN thanks the Management of SRM, India, for their support.
Allen, F. H., Kennard, O., Watson, D., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Blessing, R. H. (1995). Acta Cryst. A51, 33–38.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, T. G., Chen, T. L., Chang, H. C., Tai, Y. T., Cherng, Y. G., Chang, Y. T. & Chen, R. M. (2006). Toxicol. Appl. Pharmacol. 219, 42–53.
Erdsack, J., Schürmann, M., Preut, H. & Krause, N. (2007). Acta Cryst. E63, o664–o665.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Huang, A. C., Lin, T. P., Weng, Y. S., Ho, Y. T., Lin, H. J., Huang, L. J., Kuo, S. C. & Chung, J. G. (2007). Anticancer Res. 27, 2505–2514.
Lin, J. G., Chen, G. W., Li, T. M., Chouh, S. T., Tan, T. W. & Chung, J. G. (2006). J. Urol. 175, 343–347.
Lu, K. W., Tsai, M. L., Chen, J. C., Hsu, S. C., Hsia, T. C., Lin, M. W., Huang, A. C., Chang, Y. H., Ip, S. W., Lu, H. F. & Chung, J. G. (2008). Anticancer Res. 28, 1093–1099.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.
Zhang, L. & Wei, L. J. (2007). Life Sci. 80 , 1189–1197.
Human cervical cancer is potentially lethal, and therefore the development of effective and tolerable therapeutic options is vital (Huang et al., 2007; Lu et al., 2008). Dihydrofuran carboxylate compounds induced morphological changes and cytotoxicity in a dose - dependent manner. Dihydrofuran carboxylate compounds induced apoptosis which was analyzed by flow cytometric methods and confirmed by DAPI staining and DNA fragmentation analyzed by DNA gel electrophoresis (Chen et al., 2006; Lin et al., 2006; Zhang & Wei, 2007). In view of this medicinal importance, an X-ray study of the title compound, (I), was carried out.
An ORTEP (Farrugia,1997) plot of the molecule is shown in Fig. 1. The bond lengths in (I) show normal values (Allen et al., 1987) and are comparable to the related structure (Erdsack et al., 2007). The dihydrofuran ring (O2/C1—C4) is planar with a maximum deviation of -0.021 (2)° for C3 from the least square plane defined by all non hydrogen atoms in the molecule. The dihydrofuran ring makes dihedral angles of 28.1 (7)° and 54.5 (5)°, respectively, with the benzyl ring (C12—C17) and phenylamino ring (C5—C10), whereas the benzyl and phenylamino rings are oriented at an angle of 78.6 (6)° with respect to each other.
The crystal structure is stabilized by intramolecular N—H···O interactions. In addition to the van der Waals interactions, the molecular packing in the crystal is also stabilized by intermolecular C—H···O interactions (Table 1, Fig. 2).