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access1-(2-Methoxyphenyl)-1H-pyrrole-2,5-dione
aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com
In the title compound, C11H9NO3, the dihedral angle between the methoxybenzene and 1H-pyrrole-2,5-dione rings is 75.60 (10)°. The C atom of the methoxy group is close to coplanar with its attached ring [deviation = 0.208 (2) Å]. In the crystal, weak aromatic π–π stacking [centroid–centroid separation = 3.8563 (13) Å] occurs between inversion-related pairs of benzene rings.
![[Scheme 1]](hb6853scheme1.gif)
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2007![[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]](../../../../../../logos/arrows/e_arr.gif "Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.")
); cell SAINT (Bruker, 2007); 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 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.
Supporting information
contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812026888/hb6853sup1.cif
Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812026888/hb6853Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812026888/hb6853Isup3.cml
Equimolar quantities of 2-methoxyaniline and furan-2,5-dione (maleic anhydride) were stirred in acetic acid for 2 h. The solution was kept at room temperature which afforded light yellow prisms after two days.
Twin was found in the data with twin matrix [1, 0, 0.653: 0, -1, 0: 0, 0, -1]. Using the standard techniques, the twin was removed with Basf = 0.07458.
The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for other H-atoms.
The title compound (I), (Fig. 1) is present as a fragment of the of 4-(2-methoxyphenyl)-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (Carroll et al., 2011).
In (I) the methoxybenzene A (C1—C7/O1) and 1H-pyrrole-2,5-dione B (C8—C11/N1/O2/O3) are close to planar with r.m.s. deviation of 0.0461 and 0.0201 Å, respectively. The dihedral angle between A/B is 78.22 (5)°.
For a related structure, see: Carroll et al., (2011).
Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
![[Figure 1]](./hb6853fig1thm.gif) | Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level. |
| C11H9NO3 | F(000) = 424 |
| Mr = 203.19 | Dx = 1.412 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1267 reflections |
| a = 12.7018 (15) Å | θ = 1.6–26.0° |
| b = 10.2689 (12) Å | µ = 0.10 mm−1 |
| c = 7.4695 (8) Å | T = 296 K |
| β = 101.067 (7)° | Prism, light yellow |
| V = 956.16 (19) Å3 | 0.30 × 0.25 × 0.23 mm |
| Z = 4 |
| Bruker Kappa APEXII CCD diffractometer | 1887 independent reflections |
| Radiation source: fine-focus sealed tube | 1267 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.030 |
| Detector resolution: 8.00 pixels mm-1 | θmax = 26.0°, θmin = 1.9° |
| ω scans | h = −12→15 |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −12→9 |
| Tmin = 0.969, Tmax = 0.977 | l = −9→9 |
| 7388 measured reflections |
| 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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.112 | H-atom parameters constrained |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.051P)2 + 0.1053P] where P = (Fo2 + 2Fc2)/3 |
| 1887 reflections | (Δ/σ)max < 0.001 |
| 137 parameters | Δρmax = 0.11 e Å−3 |
| 0 restraints | Δρmin = −0.19 e Å−3 |
| C11H9NO3 | V = 956.16 (19) Å3 |
| Mr = 203.19 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 12.7018 (15) Å | µ = 0.10 mm−1 |
| b = 10.2689 (12) Å | T = 296 K |
| c = 7.4695 (8) Å | 0.30 × 0.25 × 0.23 mm |
| β = 101.067 (7)° |
| Bruker Kappa APEXII CCD diffractometer | 1887 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1267 reflections with I > 2σ(I) |
| Tmin = 0.969, Tmax = 0.977 | Rint = 0.030 |
| 7388 measured reflections |
| R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
| wR(F2) = 0.112 | H-atom parameters constrained |
| S = 1.01 | Δρmax = 0.11 e Å−3 |
| 1887 reflections | Δρmin = −0.19 e Å−3 |
| 137 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 | 0.20496 (11) | 0.44118 (13) | −0.18267 (18) | 0.0604 (4) | |
| O2 | 0.08846 (11) | 0.44793 (14) | 0.1941 (2) | 0.0692 (5) | |
| O3 | 0.28200 (11) | 0.79126 (14) | 0.0549 (2) | 0.0724 (5) | |
| N1 | 0.20700 (11) | 0.59539 (14) | 0.11254 (19) | 0.0438 (4) | |
| C1 | 0.29485 (14) | 0.51130 (17) | 0.1042 (3) | 0.0447 (4) | |
| C2 | 0.29351 (15) | 0.43286 (17) | −0.0476 (3) | 0.0476 (5) | |
| C3 | 0.38002 (18) | 0.35292 (19) | −0.0525 (3) | 0.0619 (6) | |
| H3 | 0.3800 | 0.2986 | −0.1522 | 0.074* | |
| C4 | 0.46654 (18) | 0.3536 (2) | 0.0903 (4) | 0.0708 (7) | |
| H4 | 0.5250 | 0.3001 | 0.0854 | 0.085* | |
| C5 | 0.46810 (18) | 0.4312 (2) | 0.2383 (3) | 0.0698 (7) | |
| H5 | 0.5271 | 0.4308 | 0.3338 | 0.084* | |
| C6 | 0.38151 (16) | 0.5103 (2) | 0.2455 (3) | 0.0577 (5) | |
| H6 | 0.3818 | 0.5633 | 0.3465 | 0.069* | |
| C7 | 0.2079 (2) | 0.3746 (2) | −0.3493 (3) | 0.0789 (7) | |
| H7A | 0.2684 | 0.4044 | −0.3978 | 0.118* | |
| H7B | 0.1430 | 0.3920 | −0.4355 | 0.118* | |
| H7C | 0.2142 | 0.2827 | −0.3267 | 0.118* | |
| C8 | 0.11142 (15) | 0.55756 (19) | 0.1598 (2) | 0.0478 (5) | |
| C9 | 0.04849 (15) | 0.6775 (2) | 0.1639 (3) | 0.0556 (5) | |
| H9 | −0.0208 | 0.6816 | 0.1871 | 0.067* | |
| C10 | 0.10532 (15) | 0.7772 (2) | 0.1297 (3) | 0.0560 (5) | |
| H10 | 0.0840 | 0.8639 | 0.1280 | 0.067* | |
| C11 | 0.20922 (15) | 0.72958 (18) | 0.0941 (2) | 0.0489 (5) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0631 (9) | 0.0606 (9) | 0.0594 (9) | 0.0035 (7) | 0.0164 (7) | −0.0146 (7) |
| O2 | 0.0603 (9) | 0.0562 (9) | 0.0953 (12) | −0.0116 (7) | 0.0252 (8) | 0.0111 (8) |
| O3 | 0.0643 (9) | 0.0516 (9) | 0.1068 (12) | −0.0081 (8) | 0.0303 (9) | 0.0103 (8) |
| N1 | 0.0435 (8) | 0.0362 (8) | 0.0552 (9) | −0.0021 (7) | 0.0183 (7) | −0.0045 (7) |
| C1 | 0.0419 (10) | 0.0386 (10) | 0.0578 (12) | 0.0002 (8) | 0.0198 (9) | 0.0032 (8) |
| C2 | 0.0498 (11) | 0.0381 (10) | 0.0600 (12) | 0.0010 (9) | 0.0232 (10) | 0.0045 (8) |
| C3 | 0.0695 (14) | 0.0451 (12) | 0.0814 (15) | 0.0089 (11) | 0.0403 (13) | 0.0056 (10) |
| C4 | 0.0571 (14) | 0.0572 (15) | 0.107 (2) | 0.0192 (11) | 0.0393 (14) | 0.0293 (14) |
| C5 | 0.0532 (13) | 0.0739 (16) | 0.0824 (17) | 0.0082 (12) | 0.0137 (12) | 0.0250 (14) |
| C6 | 0.0539 (12) | 0.0576 (13) | 0.0621 (13) | −0.0011 (10) | 0.0125 (10) | 0.0076 (10) |
| C7 | 0.0974 (18) | 0.0750 (16) | 0.0687 (15) | −0.0085 (14) | 0.0271 (13) | −0.0231 (12) |
| C8 | 0.0437 (11) | 0.0507 (12) | 0.0504 (11) | −0.0071 (9) | 0.0129 (9) | −0.0012 (9) |
| C9 | 0.0436 (10) | 0.0657 (14) | 0.0598 (12) | 0.0055 (10) | 0.0155 (9) | −0.0050 (10) |
| C10 | 0.0547 (12) | 0.0471 (12) | 0.0665 (13) | 0.0090 (10) | 0.0123 (10) | −0.0067 (9) |
| C11 | 0.0497 (11) | 0.0431 (11) | 0.0546 (11) | −0.0018 (9) | 0.0121 (9) | −0.0012 (9) |
| O1—C2 | 1.362 (2) | C4—H4 | 0.9300 |
| O1—C7 | 1.426 (2) | C5—C6 | 1.377 (3) |
| O2—C8 | 1.203 (2) | C5—H5 | 0.9300 |
| O3—C11 | 1.202 (2) | C6—H6 | 0.9300 |
| N1—C8 | 1.383 (2) | C7—H7A | 0.9600 |
| N1—C11 | 1.386 (2) | C7—H7B | 0.9600 |
| N1—C1 | 1.422 (2) | C7—H7C | 0.9600 |
| C1—C6 | 1.371 (3) | C8—C9 | 1.471 (3) |
| C1—C2 | 1.388 (3) | C9—C10 | 1.307 (3) |
| C2—C3 | 1.378 (3) | C9—H9 | 0.9300 |
| C3—C4 | 1.377 (3) | C10—C11 | 1.479 (3) |
| C3—H3 | 0.9300 | C10—H10 | 0.9300 |
| C4—C5 | 1.360 (3) | ||
| C2—O1—C7 | 117.40 (17) | C1—C6—H6 | 119.9 |
| C8—N1—C11 | 109.89 (15) | C5—C6—H6 | 119.9 |
| C8—N1—C1 | 125.12 (15) | O1—C7—H7A | 109.5 |
| C11—N1—C1 | 124.64 (15) | O1—C7—H7B | 109.5 |
| C6—C1—C2 | 120.45 (18) | H7A—C7—H7B | 109.5 |
| C6—C1—N1 | 119.44 (17) | O1—C7—H7C | 109.5 |
| C2—C1—N1 | 120.10 (17) | H7A—C7—H7C | 109.5 |
| O1—C2—C3 | 124.53 (18) | H7B—C7—H7C | 109.5 |
| O1—C2—C1 | 116.59 (16) | O2—C8—N1 | 125.28 (18) |
| C3—C2—C1 | 118.9 (2) | O2—C8—C9 | 128.61 (18) |
| C4—C3—C2 | 119.9 (2) | N1—C8—C9 | 106.09 (16) |
| C4—C3—H3 | 120.1 | C10—C9—C8 | 109.24 (17) |
| C2—C3—H3 | 120.1 | C10—C9—H9 | 125.4 |
| C5—C4—C3 | 121.2 (2) | C8—C9—H9 | 125.4 |
| C5—C4—H4 | 119.4 | C9—C10—C11 | 108.73 (17) |
| C3—C4—H4 | 119.4 | C9—C10—H10 | 125.6 |
| C4—C5—C6 | 119.4 (2) | C11—C10—H10 | 125.6 |
| C4—C5—H5 | 120.3 | O3—C11—N1 | 125.41 (17) |
| C6—C5—H5 | 120.3 | O3—C11—C10 | 128.60 (18) |
| C1—C6—C5 | 120.3 (2) | N1—C11—C10 | 105.98 (16) |
| C8—N1—C1—C6 | −100.8 (2) | N1—C1—C6—C5 | −178.87 (17) |
| C11—N1—C1—C6 | 71.7 (2) | C4—C5—C6—C1 | −0.3 (3) |
| C8—N1—C1—C2 | 80.5 (2) | C11—N1—C8—O2 | −176.12 (18) |
| C11—N1—C1—C2 | −107.0 (2) | C1—N1—C8—O2 | −2.7 (3) |
| C7—O1—C2—C3 | −8.0 (3) | C11—N1—C8—C9 | 2.25 (19) |
| C7—O1—C2—C1 | 172.00 (17) | C1—N1—C8—C9 | 175.70 (16) |
| C6—C1—C2—O1 | −179.12 (16) | O2—C8—C9—C10 | 175.7 (2) |
| N1—C1—C2—O1 | −0.4 (2) | N1—C8—C9—C10 | −2.6 (2) |
| C6—C1—C2—C3 | 0.9 (3) | C8—C9—C10—C11 | 1.9 (2) |
| N1—C1—C2—C3 | 179.59 (15) | C8—N1—C11—O3 | 179.57 (19) |
| O1—C2—C3—C4 | 178.86 (17) | C1—N1—C11—O3 | 6.1 (3) |
| C1—C2—C3—C4 | −1.1 (3) | C8—N1—C11—C10 | −1.15 (19) |
| C2—C3—C4—C5 | 0.7 (3) | C1—N1—C11—C10 | −174.64 (16) |
| C3—C4—C5—C6 | 0.1 (3) | C9—C10—C11—O3 | 178.7 (2) |
| C2—C1—C6—C5 | −0.1 (3) | C9—C10—C11—N1 | −0.5 (2) |
Experimental details
| Crystal data | |
| Chemical formula | C11H9NO3 |
| Mr | 203.19 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 296 |
| a, b, c (Å) | 12.7018 (15), 10.2689 (12), 7.4695 (8) |
| β (°) | 101.067 (7) |
| V (Å3) | 956.16 (19) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.10 |
| Crystal size (mm) | 0.30 × 0.25 × 0.23 |
| Data collection | |
| Diffractometer | Bruker Kappa APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
| Tmin, Tmax | 0.969, 0.977 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 7388, 1887, 1267 |
| Rint | 0.030 |
| (sin θ/λ)max (Å−1) | 0.617 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.112, 1.01 |
| No. of reflections | 1887 |
| No. of parameters | 137 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.11, −0.19 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
Acknowledgements
The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.
References
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Carroll, W. R., Zhao, C., Smith, M. D., Pellechia, P. J. & Shimizu, K. D. (2011). Org. Lett. 13, 4320–4323. Web of Science CSD CrossRef CAS PubMed Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
The title compound (I), (Fig. 1) is present as a fragment of the crystal structure of 4-(2-methoxyphenyl)-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (Carroll et al., 2011).
In (I) the methoxybenzene A (C1—C7/O1) and 1H-pyrrole-2,5-dione B (C8—C11/N1/O2/O3) are close to planar with r.m.s. deviation of 0.0461 and 0.0201 Å, respectively. The dihedral angle between A/B is 78.22 (5)°.