| N-(4-Butanoyl-3-hy-droxy-phen-yl)butanamide. | |
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MedLine Citation:
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PMID: 21523105 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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The title compound, C(14)H(19)NO(3), was prepared via the intra-molecular rearrangement of 3-(butanoyl-amino)-phenyl butano-ate in the presence of anhydrous aluminium chloride. The near coplanarity of the aromatic ring, the amide group and the carbonyl group of the butanoyl fragment [N-C-C-C = -179.65 (17) and O-C-C-C = -178.34 (17)°] results from the intra-molecular O-H⋯O and C-H⋯O hydrogen bonds. In the crystal, the mol-ecules form a one-dimensional polymeric structure via N-H⋯O inter-actions between their amide groups. |
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Authors:
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Ming-Ming Yang; Fang-Shi Li; Qi-Sheng Lu; Hao-Wei Wang; Qing Xie |
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Publication Detail:
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Type: Journal Article Date: 2011-01-22 |
Journal Detail:
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Title: Acta crystallographica. Section E, Structure reports online Volume: 67 ISSN: 1600-5368 ISO Abbreviation: Acta Crystallogr E Struct Rep Online Publication Date: 2011 |
Date Detail:
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Created Date: 2011-04-27 Completed Date: 2011-07-14 Revised Date: 2011-11-11 |
Medline Journal Info:
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Nlm Unique ID: 101089178 Medline TA: Acta Crystallogr E Struct Rep Online Country: England |
Other Details:
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Languages: eng Pagination: o441 Citation Subset: - |
Affiliation:
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Department of Applied Chemistry, College of Science, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing 210009, People's Republic of China. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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Journal Information Journal ID (nlm-ta): Acta Crystallogr Sect E Struct Rep Online Journal ID (publisher-id): Acta Cryst. E ISSN: 1600-5368 Publisher: International Union of Crystallography |
Article Information Download PDF  A full version of this article is available from Crystallography Journals Online.© Yang et al. 2011 open-access: Received Day: 14 Month: 12 Year: 2010 Accepted Day: 10 Month: 1 Year: 2011 collection publication date: Day: 01 Month: 2 Year: 2011 Electronic publication date: Day: 22 Month: 1 Year: 2011 pmc-release publication date: Day: 22 Month: 1 Year: 2011 Volume: 67 Issue: Pt 2 First Page: o441 Last Page: o441 ID: 3051673 PubMed Id: 21523105 Publisher Id: gk2334 DOI: 10.1107/S1600536811001279 Coden: ACSEBH Publisher Item Identifier: S1600536811001279 |
| N-(4-Butanoyl-3-hydroxyphenyl)butanamide Alternate Title:C14H19NO3 | |
| Ming-Ming Yanga | |
| Fang-Shi Lia* | |
| Qi-Sheng Lua | |
| Hao-Wei Wanga | |
| Qing Xiea | |
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aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing 210009, People’s Republic of China |
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| Correspondence: Correspondence e-mail: fangshi.li@njut.edu.cn |
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Related literature
For the synthesis, see: Wang et al. (2006 ▶).[Chemical Structure ID: scheme1]
Experimental
Crystal data
- C14H19NO3
- Mr = 249.30
- Monoclinic,
- a = 6.2870 (13) Å
- b = 10.008 (2) Å
- c = 21.680 (4) Å
- β = 97.96 (3)°
- V = 1351.0 (5) Å3
- Z = 4
- Mo Kα radiation
- μ = 0.09 mm−1
- T = 293 K
- 0.30 × 0.20 × 0.20 mm
Data collection
- Enraf–Nonius CAD-4 diffractometer
- Absorption correction: ψ scan (North et al., 1968 ▶) Tmin = 0.975, Tmax = 0.983
- 2684 measured reflections
- 2448 independent reflections
- 1732 reflections with I > 2σ(I)
- Rint = 0.035
- 3 standard reflections every 200 reflections intensity decay: 1%
Refinement
- R[F2 > 2σ(F2)] = 0.050
- wR(F2) = 0.160
- S = 1.00
- 2448 reflections
- 164 parameters
- H-atom parameters constrained
- Δρmax = 0.19 e Å−3
- Δρmin = −0.18 e Å−3
Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.
Notes
fnu1Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2334).
The authors thank the Center of Testing and Analysis, Nanjing University, for support.
supplementary crystallographic
information
Comment
The title compound is an important intermediate for the synthesis of an anticoccidial drug Nequinate. It was prepared via intramolecular rearrangement of 3-(butanoylamino)phenyl butanoate in 1,2-dichloroethane in the presence of anhydrous aluminium chloride. We report here the crystal structure of the title compound.
The molecular structure is shown in Fig. 1.
In the crystal, molecules are linked via intermolecular N—H···O hydrogen bond to form chains.
Experimental
The title compound (m.p. 381 K) was prepared by a method reported by Wang et al. (2006). The crystals were obtained from methanolic solution by slow evaporation.
Refinement
All H atoms were positioned geometrically, with O—H = 0.82 Å, N—H = 0.86 Å and C—H = 0.93-0.97 Å, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C,N,O).
Figures
Crystal data
Data collection
Refinement
Special details
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
Atomic displacement parameters (Å2)
Geometric parameters (Å, °)
Hydrogen-bond geometry (Å, °)
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2.
References
| Enraf–Nonius (1985). CAD-4 Software Enraf–Nonius, Delft, The Netherlands. | |
| Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany. | |
| North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. | |
| Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. | |
| Wang, X. Z., Zhang, S. J., Dai, L. Y. & Chen, Y. Q. (2006). CN Patent No. 173303. |
Figures
[Figure ID: Fap1] |
Fig. 1.
Molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown by dashed lines. |
[Figure ID: Fap2] |
Fig. 2.
A packing diagram. Hhydrogen bond is shown by dashed lines. |
Tables
[TableWrap ID: d1e116]
| C14H19NO3 | F(000) = 536 |
| Mr = 249.30 | Dx = 1.226 Mg m−3 |
| Monoclinic, P21/n | Melting point: 381 K |
| Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
| a = 6.2870 (13) Å | Cell parameters from 25 reflections |
| b = 10.008 (2) Å | θ = 10–13° |
| c = 21.680 (4) Å | µ = 0.09 mm−1 |
| β = 97.96 (3)° | T = 293 K |
| V = 1351.0 (5) Å3 | Plate, colorless |
| Z = 4 | 0.30 × 0.20 × 0.20 mm |
[TableWrap ID: d1e244]
| Enraf–Nonius CAD-4 diffractometer | 1732 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.035 |
| graphite | θmax = 25.3°, θmin = 1.9° |
| ω/2θ scans | h = 0→7 |
| Absorption correction: ψ scan (North et al., 1968) | k = 0→12 |
| Tmin = 0.975, Tmax = 0.983 | l = −26→25 |
| 2684 measured reflections | 3 standard reflections every 200 reflections |
| 2448 independent reflections | intensity decay: 1% |
[TableWrap ID: d1e363]
| 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)] = 0.050 | H-atom parameters constrained |
| wR(F2) = 0.160 | w = 1/[σ2(Fo2) + (0.1P)2 + 0.080P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.00 | (Δ/σ)max < 0.001 |
| 2448 reflections | Δρmax = 0.19 e Å−3 |
| 164 parameters | Δρmin = −0.18 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.045 (6) |
[TableWrap ID: d1e544]
| 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. |
[TableWrap ID: d1e643]
| x | y | z | Uiso*/Ueq | ||
| N1 | 0.1152 (3) | 0.62012 (16) | 0.25206 (8) | 0.0443 (5) | |
| H1N | 0.1438 | 0.7034 | 0.2480 | 0.053* | |
| O1 | 0.2269 (3) | 0.41334 (15) | 0.22806 (8) | 0.0653 (5) | |
| O2 | −0.3406 (3) | 0.31968 (14) | 0.34457 (8) | 0.0624 (5) | |
| H2A | −0.4387 | 0.3191 | 0.3659 | 0.094* | |
| O3 | −0.6164 (3) | 0.41920 (16) | 0.40749 (9) | 0.0686 (5) | |
| C1 | 0.1729 (6) | 0.5577 (3) | 0.07966 (14) | 0.0959 (10) | |
| H1A | 0.1779 | 0.5148 | 0.0403 | 0.144* | |
| H1B | 0.1475 | 0.6515 | 0.0732 | 0.144* | |
| H1C | 0.0590 | 0.5196 | 0.0992 | 0.144* | |
| C2 | 0.3834 (5) | 0.5374 (2) | 0.12083 (11) | 0.0668 (7) | |
| H2B | 0.4978 | 0.5753 | 0.1006 | 0.080* | |
| H2C | 0.4104 | 0.4423 | 0.1259 | 0.080* | |
| C3 | 0.3882 (4) | 0.6008 (2) | 0.18464 (11) | 0.0547 (6) | |
| H3A | 0.5332 | 0.5959 | 0.2067 | 0.066* | |
| H3B | 0.3502 | 0.6945 | 0.1795 | 0.066* | |
| C4 | 0.2373 (3) | 0.5346 (2) | 0.22330 (10) | 0.0445 (5) | |
| C5 | −0.0507 (3) | 0.59311 (17) | 0.28740 (9) | 0.0398 (5) | |
| C6 | −0.1165 (3) | 0.46492 (18) | 0.29964 (10) | 0.0442 (5) | |
| H6A | −0.0497 | 0.3914 | 0.2844 | 0.053* | |
| C7 | −0.2832 (3) | 0.44685 (19) | 0.33483 (9) | 0.0444 (5) | |
| C8 | −0.3858 (3) | 0.55602 (19) | 0.35889 (9) | 0.0425 (5) | |
| C9 | −0.3162 (3) | 0.6842 (2) | 0.34437 (9) | 0.0453 (5) | |
| H9A | −0.3830 | 0.7585 | 0.3589 | 0.054* | |
| C10 | −0.1537 (3) | 0.70308 (19) | 0.30956 (9) | 0.0442 (5) | |
| H10A | −0.1116 | 0.7892 | 0.3006 | 0.053* | |
| C11 | −0.5560 (3) | 0.5341 (2) | 0.39762 (10) | 0.0490 (5) | |
| C12 | −0.6540 (3) | 0.6497 (2) | 0.42757 (10) | 0.0534 (6) | |
| H12A | −0.7122 | 0.7119 | 0.3953 | 0.064* | |
| H12B | −0.5417 | 0.6957 | 0.4547 | 0.064* | |
| C13 | −0.8299 (4) | 0.6116 (3) | 0.46512 (10) | 0.0580 (6) | |
| H13A | −0.7728 | 0.5484 | 0.4971 | 0.070* | |
| H13B | −0.9440 | 0.5673 | 0.4380 | 0.070* | |
| C14 | −0.9232 (5) | 0.7300 (3) | 0.49570 (12) | 0.0794 (8) | |
| H14A | −1.0325 | 0.6996 | 0.5192 | 0.119* | |
| H14B | −0.9846 | 0.7916 | 0.4642 | 0.119* | |
| H14C | −0.8115 | 0.7738 | 0.5231 | 0.119* |
[TableWrap ID: d1e1172]
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0468 (10) | 0.0330 (9) | 0.0537 (10) | −0.0018 (7) | 0.0090 (8) | 0.0002 (7) |
| O1 | 0.0714 (11) | 0.0388 (9) | 0.0915 (13) | 0.0046 (7) | 0.0315 (10) | −0.0037 (8) |
| O2 | 0.0734 (11) | 0.0376 (9) | 0.0804 (11) | −0.0086 (7) | 0.0251 (9) | 0.0033 (7) |
| O3 | 0.0702 (11) | 0.0529 (10) | 0.0876 (12) | −0.0110 (8) | 0.0286 (10) | 0.0042 (8) |
| C1 | 0.125 (3) | 0.087 (2) | 0.0665 (18) | 0.0120 (19) | −0.0203 (18) | −0.0066 (15) |
| C2 | 0.0887 (18) | 0.0555 (14) | 0.0596 (15) | 0.0114 (13) | 0.0224 (14) | 0.0024 (12) |
| C3 | 0.0519 (13) | 0.0520 (13) | 0.0619 (14) | −0.0067 (10) | 0.0140 (11) | −0.0059 (11) |
| C4 | 0.0425 (11) | 0.0398 (12) | 0.0503 (12) | 0.0007 (9) | 0.0038 (9) | −0.0037 (9) |
| C5 | 0.0397 (11) | 0.0354 (10) | 0.0423 (11) | −0.0005 (8) | −0.0019 (9) | 0.0007 (8) |
| C6 | 0.0471 (11) | 0.0334 (11) | 0.0517 (12) | 0.0029 (9) | 0.0053 (10) | −0.0021 (9) |
| C7 | 0.0499 (12) | 0.0332 (10) | 0.0482 (12) | −0.0042 (9) | −0.0006 (9) | 0.0016 (9) |
| C8 | 0.0412 (11) | 0.0404 (11) | 0.0439 (11) | −0.0033 (9) | −0.0004 (9) | 0.0013 (9) |
| C9 | 0.0477 (12) | 0.0390 (11) | 0.0496 (12) | 0.0025 (9) | 0.0073 (10) | −0.0038 (9) |
| C10 | 0.0498 (12) | 0.0309 (10) | 0.0520 (12) | −0.0022 (9) | 0.0070 (10) | 0.0006 (9) |
| C11 | 0.0460 (12) | 0.0486 (13) | 0.0505 (12) | −0.0040 (10) | −0.0008 (10) | 0.0028 (9) |
| C12 | 0.0493 (12) | 0.0573 (14) | 0.0540 (13) | −0.0039 (10) | 0.0087 (10) | −0.0011 (11) |
| C13 | 0.0551 (13) | 0.0691 (15) | 0.0512 (13) | −0.0006 (11) | 0.0119 (11) | 0.0037 (11) |
| C14 | 0.089 (2) | 0.084 (2) | 0.0723 (17) | −0.0043 (15) | 0.0356 (16) | −0.0064 (14) |
[TableWrap ID: d1e1538]
| N1—C4 | 1.357 (3) | C6—C7 | 1.390 (3) |
| N1—C5 | 1.403 (2) | C6—H6A | 0.9300 |
| N1—H1N | 0.8600 | C7—C8 | 1.406 (3) |
| O1—C4 | 1.221 (2) | C8—C9 | 1.405 (3) |
| O2—C7 | 1.348 (2) | C8—C11 | 1.466 (3) |
| O2—H2A | 0.8200 | C9—C10 | 1.365 (3) |
| O3—C11 | 1.239 (3) | C9—H9A | 0.9300 |
| C1—C2 | 1.504 (4) | C10—H10A | 0.9300 |
| C1—H1A | 0.9600 | C11—C12 | 1.500 (3) |
| C1—H1B | 0.9600 | C12—C13 | 1.510 (3) |
| C1—H1C | 0.9600 | C12—H12A | 0.9700 |
| C2—C3 | 1.519 (3) | C12—H12B | 0.9700 |
| C2—H2B | 0.9700 | C13—C14 | 1.515 (3) |
| C2—H2C | 0.9700 | C13—H13A | 0.9700 |
| C3—C4 | 1.504 (3) | C13—H13B | 0.9700 |
| C3—H3A | 0.9700 | C14—H14A | 0.9600 |
| C3—H3B | 0.9700 | C14—H14B | 0.9600 |
| C5—C6 | 1.385 (2) | C14—H14C | 0.9600 |
| C5—C10 | 1.396 (3) | ||
| C4—N1—C5 | 129.76 (17) | O2—C7—C8 | 121.95 (19) |
| C4—N1—H1N | 115.1 | C6—C7—C8 | 121.46 (18) |
| C5—N1—H1N | 115.1 | C9—C8—C7 | 116.97 (18) |
| C7—O2—H2A | 109.5 | C9—C8—C11 | 122.65 (18) |
| C2—C1—H1A | 109.5 | C7—C8—C11 | 120.38 (18) |
| C2—C1—H1B | 109.5 | C10—C9—C8 | 122.01 (18) |
| H1A—C1—H1B | 109.5 | C10—C9—H9A | 119.0 |
| C2—C1—H1C | 109.5 | C8—C9—H9A | 119.0 |
| H1A—C1—H1C | 109.5 | C9—C10—C5 | 120.00 (18) |
| H1B—C1—H1C | 109.5 | C9—C10—H10A | 120.0 |
| C1—C2—C3 | 112.9 (2) | C5—C10—H10A | 120.0 |
| C1—C2—H2B | 109.0 | O3—C11—C8 | 120.2 (2) |
| C3—C2—H2B | 109.0 | O3—C11—C12 | 119.15 (19) |
| C1—C2—H2C | 109.0 | C8—C11—C12 | 120.61 (18) |
| C3—C2—H2C | 109.0 | C11—C12—C13 | 114.48 (19) |
| H2B—C2—H2C | 107.8 | C11—C12—H12A | 108.6 |
| C4—C3—C2 | 112.88 (19) | C13—C12—H12A | 108.6 |
| C4—C3—H3A | 109.0 | C11—C12—H12B | 108.6 |
| C2—C3—H3A | 109.0 | C13—C12—H12B | 108.6 |
| C4—C3—H3B | 109.0 | H12A—C12—H12B | 107.6 |
| C2—C3—H3B | 109.0 | C12—C13—C14 | 113.3 (2) |
| H3A—C3—H3B | 107.8 | C12—C13—H13A | 108.9 |
| O1—C4—N1 | 123.21 (19) | C14—C13—H13A | 108.9 |
| O1—C4—C3 | 122.04 (19) | C12—C13—H13B | 108.9 |
| N1—C4—C3 | 114.76 (18) | C14—C13—H13B | 108.9 |
| C6—C5—C10 | 119.95 (18) | H13A—C13—H13B | 107.7 |
| C6—C5—N1 | 123.20 (17) | C13—C14—H14A | 109.5 |
| C10—C5—N1 | 116.84 (16) | C13—C14—H14B | 109.5 |
| C5—C6—C7 | 119.58 (18) | H14A—C14—H14B | 109.5 |
| C5—C6—H6A | 120.2 | C13—C14—H14C | 109.5 |
| C7—C6—H6A | 120.2 | H14A—C14—H14C | 109.5 |
| O2—C7—C6 | 116.59 (17) | H14B—C14—H14C | 109.5 |
| C1—C2—C3—C4 | 67.0 (3) | C6—C7—C8—C11 | −177.91 (18) |
| C5—N1—C4—O1 | −5.1 (3) | C7—C8—C9—C10 | −1.3 (3) |
| C5—N1—C4—C3 | 174.86 (19) | C11—C8—C9—C10 | 178.29 (19) |
| C2—C3—C4—O1 | 46.3 (3) | C8—C9—C10—C5 | −0.2 (3) |
| C2—C3—C4—N1 | −133.7 (2) | C6—C5—C10—C9 | 1.4 (3) |
| C4—N1—C5—C6 | 1.0 (3) | N1—C5—C10—C9 | −179.87 (17) |
| C4—N1—C5—C10 | −177.72 (19) | C9—C8—C11—O3 | 177.71 (19) |
| C10—C5—C6—C7 | −1.0 (3) | C7—C8—C11—O3 | −2.7 (3) |
| N1—C5—C6—C7 | −179.65 (17) | C9—C8—C11—C12 | −4.4 (3) |
| C5—C6—C7—O2 | 179.43 (17) | C7—C8—C11—C12 | 175.14 (18) |
| C5—C6—C7—C8 | −0.6 (3) | O3—C11—C12—C13 | −3.1 (3) |
| O2—C7—C8—C9 | −178.34 (17) | C8—C11—C12—C13 | 179.01 (18) |
| C6—C7—C8—C9 | 1.7 (3) | C11—C12—C13—C14 | 179.02 (19) |
| O2—C7—C8—C11 | 2.1 (3) |
[TableWrap ID: d1e2179]
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O1i | 0.86 | 2.29 | 3.109 (2) | 160 |
| O2—H2A···O3 | 0.82 | 1.83 | 2.552 (3) | 146 |
| C6—H6A···O1 | 0.93 | 2.27 | 2.875 (3) | 122 |
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