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access4-(4-Nitrophenyl)morpholine
aState Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China, and bDepartment of Applied Chemistry, College of Chemical Engineering, Sichuan University, Chengdu 610041, People's Republic of China
*Correspondence e-mail: yangli@scu.edu.cn
Aromatic π–π stacking interactions stabilize the of the title compound, C10H12N2O3, the perpendicular distance between parallel planes being 3.7721 (8) Å. The morpholine ring adopts a chair comformation.
Related literature
For the biological activity and synthesis of 4-(4-nitrophenyl)morpholine derivatives, see: Wang et al. (2010![[Wang, S. D., Midgley, C. A., Scaerou, F., Grabarek, J. B., Griffiths, G., Jackson, W., Kontopidis, G., McClue, S. J., McInnes, C., Meades, C., Mezna, M., Plater, A., Stuart, I., Thomas, M. P., Wood, G., Clarke, R. G., Blake, D. G., Zheleva, D. I., Lane, D. P., Jackson, R. C., Glover, D. M. & Fischer, P. M. (2010). J. Med. Chem. 53, 4367-4378.]](../../../../../../logos/arrows/e_arr.gif "Wang, S. D., Midgley, C. A., Scaerou, F., Grabarek, J. B., Griffiths, G., Jackson, W., Kontopidis, G., McClue, S. J., McInnes, C., Meades, C., Mezna, M., Plater, A., Stuart, I., Thomas, M. P., Wood, G., Clarke, R. G., Blake, D. G., Zheleva, D. I., Lane, D. P., Jackson, R. C., Glover, D. M. & Fischer, P. M. (2010). J. Med. Chem. 53, 4367-4378.")
). For a related structure, see: Yang et al. (2011).
![[Scheme 1]](kj2195scheme1.gif)
Experimental
Crystal data
|
Data collection: CrysAlis PRO (Oxford Diffraction, 2006); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2.
Supporting information
contains datablocks global, I. DOI: 10.1107/S1600536812012172/kj2195sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536812012172/kj2195Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812012172/kj2195Isup3.cml
The title compound was prepared by a method similar to that of Shudong Wang et al. (2010), which Crystals suitable for X-ray analysis were obtained by slow evaporation from a solution of dichloromethane.
4-(4-nitrophenyl)morpholine derivatives are of great importance due to their anticancer activity (Wang et al., 2010;). The title compound is one of the key intermediates in our synthetic investigations of antitumor drugs. We synthesized the title compound and report its in this paper.
In the title compound, C10H12N2O3, (Fig. 1) the bond lengths and angles are within normal ranges (Yang et al., 2011). Aromatic π–π stacking interactions help to stabilize the (Fig. 2). The perpendicular distance between the parallel ring planes is 3.7721 (8) Å, the distance between the centres of gravity Cg—Cg(-x,-y,1 - z) is 3.8499 (11) Å.
For the biological activity and synthesis of 4-(4-nitrophenyl)morpholine derivatives, see: Wang et al. (2010). For a related structure, see: Yang et al. (2011).
Data collection: CrysAlis PRO (Oxford Diffraction, 2006); cell CrysAlis PRO (Oxford Diffraction, 2006); data reduction: CrysAlis PRO (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
![[Figure 1]](./kj2195fig1thm.gif) | Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. |
![[Figure 2]](./kj2195fig2thm.gif) | Fig. 2. A packing diagram of the title compound. The dotted line indicates the Cg—Cg(-x,-y,1 - z) distance. |
| C10H12N2O3 | Dx = 1.397 Mg m−3 |
| Mr = 208.22 | Mo Kα radiation, λ = 0.71073 Å |
| Orthorhombic, Pbca | Cell parameters from 1704 reflections |
| a = 14.5445 (6) Å | θ = 2.9–29.2° |
| b = 8.3832 (3) Å | µ = 0.11 mm−1 |
| c = 16.2341 (6) Å | T = 293 K |
| V = 1979.42 (13) Å3 | Block, yellow |
| Z = 8 | 0.35 × 0.33 × 0.30 mm |
| F(000) = 880 |
| Oxford Diffraction Xcalibur Eos diffractometer | 2023 independent reflections |
| Radiation source: Enhance (Mo) X-ray Source | 1377 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.018 |
| Detector resolution: 16.0874 pixels mm-1 | θmax = 26.4°, θmin = 2.9° |
| ω scans | h = −9→18 |
| Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006) | k = −6→10 |
| Tmin = 0.992, Tmax = 1.000 | l = −20→12 |
| 4949 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)] = 0.048 | Hydrogen site location: difference Fourier map |
| wR(F2) = 0.121 | All H-atom parameters refined |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.050P)2 + 0.3012P] where P = (Fo2 + 2Fc2)/3 |
| 2023 reflections | (Δ/σ)max < 0.001 |
| 184 parameters | Δρmax = 0.12 e Å−3 |
| 0 restraints | Δρmin = −0.15 e Å−3 |
| C10H12N2O3 | V = 1979.42 (13) Å3 |
| Mr = 208.22 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 14.5445 (6) Å | µ = 0.11 mm−1 |
| b = 8.3832 (3) Å | T = 293 K |
| c = 16.2341 (6) Å | 0.35 × 0.33 × 0.30 mm |
| Oxford Diffraction Xcalibur Eos diffractometer | 2023 independent reflections |
| Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006) | 1377 reflections with I > 2σ(I) |
| Tmin = 0.992, Tmax = 1.000 | Rint = 0.018 |
| 4949 measured reflections |
| R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
| wR(F2) = 0.121 | All H-atom parameters refined |
| S = 1.03 | Δρmax = 0.12 e Å−3 |
| 2023 reflections | Δρmin = −0.15 e Å−3 |
| 184 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 | 0.11977 (11) | 0.40333 (15) | 0.24876 (9) | 0.0774 (5) | |
| O2 | 0.15361 (12) | −0.3154 (2) | 0.66760 (10) | 0.0931 (6) | |
| O3 | 0.09389 (13) | −0.47156 (17) | 0.57725 (10) | 0.0907 (6) | |
| N1 | 0.12607 (10) | 0.15429 (16) | 0.36653 (8) | 0.0488 (4) | |
| N2 | 0.12312 (11) | −0.3406 (2) | 0.59853 (11) | 0.0642 (5) | |
| C1 | 0.17590 (18) | 0.4172 (3) | 0.31932 (13) | 0.0674 (6) | |
| H1A | 0.2408 (16) | 0.378 (2) | 0.3051 (12) | 0.083 (7)* | |
| H1B | 0.1775 (14) | 0.531 (2) | 0.3339 (12) | 0.072 (6)* | |
| C2 | 0.14099 (17) | 0.3205 (2) | 0.39042 (13) | 0.0587 (5) | |
| H2A | 0.1869 (14) | 0.327 (2) | 0.4354 (12) | 0.067 (6)* | |
| H2B | 0.0823 (14) | 0.367 (2) | 0.4102 (12) | 0.068 (6)* | |
| C3 | 0.07821 (15) | 0.1361 (3) | 0.28780 (11) | 0.0567 (5) | |
| H3A | 0.0113 (15) | 0.159 (2) | 0.2958 (12) | 0.081 (7)* | |
| H3B | 0.0813 (13) | 0.028 (2) | 0.2697 (11) | 0.064 (6)* | |
| C4 | 0.11879 (17) | 0.2413 (2) | 0.22354 (13) | 0.0647 (5) | |
| H4A | 0.0814 (13) | 0.237 (2) | 0.1743 (13) | 0.072 (6)* | |
| H4B | 0.1848 (14) | 0.205 (2) | 0.2122 (12) | 0.077 (6)* | |
| C5 | 0.12154 (11) | 0.03660 (19) | 0.42504 (10) | 0.0440 (4) | |
| C6 | 0.08684 (14) | −0.1153 (2) | 0.40613 (12) | 0.0589 (5) | |
| H6 | 0.0618 (13) | −0.137 (2) | 0.3546 (12) | 0.069 (6)* | |
| C7 | 0.08671 (14) | −0.2364 (2) | 0.46268 (12) | 0.0598 (5) | |
| H7 | 0.0634 (14) | −0.340 (2) | 0.4490 (12) | 0.078 (6)* | |
| C8 | 0.12173 (12) | −0.2108 (2) | 0.54007 (11) | 0.0501 (4) | |
| C9 | 0.15440 (14) | −0.0625 (2) | 0.56225 (12) | 0.0563 (5) | |
| H9 | 0.1773 (13) | −0.045 (2) | 0.6160 (13) | 0.065 (6)* | |
| C10 | 0.15375 (13) | 0.0592 (2) | 0.50585 (11) | 0.0536 (5) | |
| H10 | 0.1772 (13) | 0.161 (2) | 0.5228 (11) | 0.064 (5)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.1061 (12) | 0.0596 (8) | 0.0664 (9) | 0.0081 (8) | −0.0178 (9) | 0.0111 (7) |
| O2 | 0.1083 (13) | 0.0960 (12) | 0.0748 (11) | −0.0164 (10) | −0.0257 (10) | 0.0297 (9) |
| O3 | 0.1163 (13) | 0.0583 (9) | 0.0974 (12) | −0.0137 (9) | −0.0058 (10) | 0.0163 (8) |
| N1 | 0.0586 (9) | 0.0459 (7) | 0.0418 (8) | −0.0054 (7) | −0.0048 (7) | −0.0049 (6) |
| N2 | 0.0576 (10) | 0.0686 (11) | 0.0665 (11) | 0.0035 (9) | 0.0008 (9) | 0.0131 (9) |
| C1 | 0.0868 (16) | 0.0538 (12) | 0.0615 (13) | −0.0091 (12) | −0.0020 (12) | 0.0044 (10) |
| C2 | 0.0720 (13) | 0.0498 (10) | 0.0544 (11) | −0.0060 (10) | 0.0003 (11) | −0.0067 (9) |
| C3 | 0.0624 (13) | 0.0599 (12) | 0.0477 (11) | −0.0024 (10) | −0.0086 (9) | −0.0048 (9) |
| C4 | 0.0829 (15) | 0.0636 (12) | 0.0478 (11) | 0.0061 (12) | −0.0116 (11) | 0.0029 (9) |
| C5 | 0.0428 (9) | 0.0475 (8) | 0.0418 (9) | −0.0013 (8) | 0.0019 (7) | −0.0054 (7) |
| C6 | 0.0722 (13) | 0.0569 (11) | 0.0476 (11) | −0.0143 (10) | −0.0093 (10) | −0.0055 (9) |
| C7 | 0.0682 (12) | 0.0497 (10) | 0.0617 (12) | −0.0106 (10) | −0.0015 (10) | −0.0030 (9) |
| C8 | 0.0467 (9) | 0.0521 (9) | 0.0514 (10) | 0.0024 (8) | 0.0028 (8) | 0.0037 (8) |
| C9 | 0.0626 (12) | 0.0622 (11) | 0.0443 (10) | −0.0015 (9) | −0.0044 (9) | −0.0042 (8) |
| C10 | 0.0656 (11) | 0.0495 (9) | 0.0458 (10) | −0.0081 (9) | −0.0035 (9) | −0.0069 (8) |
| O1—C1 | 1.411 (2) | C3—H3B | 0.958 (19) |
| O1—C4 | 1.418 (2) | C3—C4 | 1.488 (3) |
| O2—N2 | 1.224 (2) | C4—H4A | 0.97 (2) |
| O3—N2 | 1.227 (2) | C4—H4B | 1.02 (2) |
| N1—C2 | 1.463 (2) | C5—C6 | 1.404 (2) |
| N1—C3 | 1.463 (2) | C5—C10 | 1.406 (2) |
| N1—C5 | 1.371 (2) | C6—H6 | 0.93 (2) |
| N2—C8 | 1.444 (2) | C6—C7 | 1.369 (3) |
| C1—H1A | 1.03 (2) | C7—H7 | 0.96 (2) |
| C1—H1B | 0.98 (2) | C7—C8 | 1.373 (3) |
| C1—C2 | 1.499 (3) | C8—C9 | 1.378 (2) |
| C2—H2A | 0.99 (2) | C9—H9 | 0.95 (2) |
| C2—H2B | 0.99 (2) | C9—C10 | 1.371 (3) |
| C3—H3A | 1.00 (2) | C10—H10 | 0.957 (18) |
| C1—O1—C4 | 108.61 (15) | O1—C4—C3 | 111.68 (18) |
| C2—N1—C3 | 113.67 (15) | O1—C4—H4A | 106.5 (11) |
| C5—N1—C2 | 120.60 (14) | O1—C4—H4B | 109.0 (11) |
| C5—N1—C3 | 120.47 (14) | C3—C4—H4A | 109.4 (11) |
| O2—N2—O3 | 122.50 (17) | C3—C4—H4B | 108.9 (11) |
| O2—N2—C8 | 118.51 (17) | H4A—C4—H4B | 111.5 (16) |
| O3—N2—C8 | 118.98 (17) | N1—C5—C6 | 121.23 (15) |
| O1—C1—H1A | 108.8 (12) | N1—C5—C10 | 122.24 (15) |
| O1—C1—H1B | 106.8 (11) | C6—C5—C10 | 116.50 (16) |
| O1—C1—C2 | 112.60 (18) | C5—C6—H6 | 121.2 (12) |
| H1A—C1—H1B | 110.1 (17) | C7—C6—C5 | 121.78 (18) |
| C2—C1—H1A | 108.2 (12) | C7—C6—H6 | 117.0 (12) |
| C2—C1—H1B | 110.3 (12) | C6—C7—H7 | 121.1 (12) |
| N1—C2—C1 | 111.18 (17) | C6—C7—C8 | 119.81 (18) |
| N1—C2—H2A | 110.4 (11) | C8—C7—H7 | 119.1 (12) |
| N1—C2—H2B | 109.4 (11) | C7—C8—N2 | 119.25 (17) |
| C1—C2—H2A | 108.0 (11) | C7—C8—C9 | 120.55 (17) |
| C1—C2—H2B | 109.2 (11) | C9—C8—N2 | 120.20 (17) |
| H2A—C2—H2B | 108.6 (16) | C8—C9—H9 | 120.3 (11) |
| N1—C3—H3A | 109.2 (12) | C10—C9—C8 | 119.62 (18) |
| N1—C3—H3B | 110.2 (11) | C10—C9—H9 | 120.1 (11) |
| N1—C3—C4 | 111.20 (16) | C5—C10—H10 | 120.4 (11) |
| H3A—C3—H3B | 105.7 (16) | C9—C10—C5 | 121.68 (17) |
| C4—C3—H3A | 111.2 (12) | C9—C10—H10 | 117.9 (11) |
| C4—C3—H3B | 109.2 (11) |
Experimental details
| Crystal data | |
| Chemical formula | C10H12N2O3 |
| Mr | 208.22 |
| Crystal system, space group | Orthorhombic, Pbca |
| Temperature (K) | 293 |
| a, b, c (Å) | 14.5445 (6), 8.3832 (3), 16.2341 (6) |
| V (Å3) | 1979.42 (13) |
| Z | 8 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.11 |
| Crystal size (mm) | 0.35 × 0.33 × 0.30 |
| Data collection | |
| Diffractometer | Oxford Diffraction Xcalibur Eos |
| Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2006) |
| Tmin, Tmax | 0.992, 1.000 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 4949, 2023, 1377 |
| Rint | 0.018 |
| (sin θ/λ)max (Å−1) | 0.625 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.121, 1.03 |
| No. of reflections | 2023 |
| No. of parameters | 184 |
| H-atom treatment | All H-atom parameters refined |
| Δρmax, Δρmin (e Å−3) | 0.12, −0.15 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).
Acknowledgements
We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.
References
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, S. D., Midgley, C. A., Scaerou, F., Grabarek, J. B., Griffiths, G., Jackson, W., Kontopidis, G., McClue, S. J., McInnes, C., Meades, C., Mezna, M., Plater, A., Stuart, I., Thomas, M. P., Wood, G., Clarke, R. G., Blake, D. G., Zheleva, D. I., Lane, D. P., Jackson, R. C., Glover, D. M. & Fischer, P. M. (2010). J. Med. Chem. 53, 4367–4378. Web of Science CrossRef CAS PubMed Google Scholar
Yang, L.-L., Zheng, R.-L., Li, G.-B., Sun, Q.-Z. & Xie, Y.-M. (2011). Acta Cryst. E67, o754. Web of Science CSD CrossRef IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
4-(4-nitrophenyl)morpholine derivatives are of great importance due to their anticancer activity (Wang et al., 2010;). The title compound is one of the key intermediates in our synthetic investigations of antitumor drugs. We synthesized the title compound and report its crystal structure in this paper.
In the title compound, C10H12N2O3, (Fig. 1) the bond lengths and angles are within normal ranges (Yang et al., 2011). Aromatic π–π stacking interactions help to stabilize the crystal structure (Fig. 2). The perpendicular distance between the parallel ring planes is 3.7721 (8) Å, the distance between the centres of gravity Cg—Cg(-x,-y,1 - z) is 3.8499 (11) Å.