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accessN′-(2-Fluorobenzylidene)acetohydrazide
aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China, bYantai Vocational and Technical institute of Engineering, Yantai 264006, People's Republic of China, and cMinistry of Personnel, Weifang University, Weifang 261061, People's Republic of China
*Correspondence e-mail: ffjian2008@163.com
The title compound, C9H9FN2O, was prepared by the reaction between 2-fluorobenzophenone and acetohydrazide. In the inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur, generating R22(8) loops.
Related literature
For background to see: Cimerman et al. (1997![[Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145-153.]](../../../../../../logos/arrows/e_arr.gif "Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145-153.")
); For related structures, see: Girgis (2006); Li & Jian (2008).
![[Scheme 1]](hb5371scheme1.gif)
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: SMART (Bruker, 1997); cell SAINT (Bruker, 1997); data reduction: SAINT; 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.
Supporting information
contains datablocks global, I. DOI: 10.1107/S1600536810010627/hb5371sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536810010627/hb5371Isup2.hkl
A mixture of 2-fluorobenzophenone (0.05 mol) and acethydrazide (0.05 mol) was stirred in refluxing ethanol(30 ml) for 4 h to afford the title compound (yield 70%). Colourless blocks of (I) were obtained by recrystallization from ethanol at room temperature.
All H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H and N—H distances in the range 0.93-0.97Å and 0.86 Å, respectively, and with Uiso(H) = 1.2Ueq of the parent atoms.
Data collection: SMART (Bruker, 1997); cell SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).
![[Figure 1]](./hb5371fig1thm.gif) | Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. |
| C9H9FN2O | F(000) = 376 |
| Mr = 180.18 | Dx = 1.355 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1515 reflections |
| a = 5.3227 (11) Å | θ = 3.2–27.5° |
| b = 8.4603 (17) Å | µ = 0.11 mm−1 |
| c = 19.656 (4) Å | T = 293 K |
| β = 93.70 (3)° | Block, colourless |
| V = 883.3 (3) Å3 | 0.30 × 0.30 × 0.20 mm |
| Z = 4 |
| Bruker SMART CCD diffractometer | 1515 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.036 |
| Graphite monochromator | θmax = 27.5°, θmin = 3.2° |
| ω scans | h = −6→6 |
| 7687 measured reflections | k = −9→10 |
| 2010 independent reflections | l = −25→25 |
| 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)] = 0.042 | H-atom parameters constrained |
| wR(F2) = 0.128 | w = 1/[σ2(Fo2) + (0.0696P)2 + 0.0888P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 2010 reflections | Δρmax = 0.14 e Å−3 |
| 119 parameters | Δρmin = −0.21 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: 0.035 (6) |
| C9H9FN2O | V = 883.3 (3) Å3 |
| Mr = 180.18 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 5.3227 (11) Å | µ = 0.11 mm−1 |
| b = 8.4603 (17) Å | T = 293 K |
| c = 19.656 (4) Å | 0.30 × 0.30 × 0.20 mm |
| β = 93.70 (3)° |
| Bruker SMART CCD diffractometer | 1515 reflections with I > 2σ(I) |
| 7687 measured reflections | Rint = 0.036 |
| 2010 independent reflections |
| R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
| wR(F2) = 0.128 | H-atom parameters constrained |
| S = 1.04 | Δρmax = 0.14 e Å−3 |
| 2010 reflections | Δρmin = −0.21 e Å−3 |
| 119 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | ||
| N2 | 0.4557 (2) | 0.26752 (14) | 0.01843 (6) | 0.0474 (3) | |
| O1 | 0.04461 (18) | 0.48232 (13) | −0.09198 (5) | 0.0578 (3) | |
| N1 | 0.2546 (2) | 0.35774 (14) | −0.00633 (6) | 0.0505 (3) | |
| H1A | 0.1453 | 0.3885 | 0.0212 | 0.061* | |
| C1 | 0.6693 (3) | 0.15209 (16) | 0.11622 (7) | 0.0479 (3) | |
| C8 | 0.2245 (2) | 0.39930 (17) | −0.07282 (7) | 0.0473 (3) | |
| C7 | 0.4679 (3) | 0.24649 (16) | 0.08270 (7) | 0.0477 (3) | |
| H7A | 0.3469 | 0.2919 | 0.1086 | 0.057* | |
| F1 | 0.5354 (2) | 0.23104 (15) | 0.22231 (5) | 0.0865 (4) | |
| C9 | 0.4142 (3) | 0.3418 (2) | −0.11987 (7) | 0.0583 (4) | |
| H9A | 0.3699 | 0.3789 | −0.1652 | 0.087* | |
| H9B | 0.4168 | 0.2284 | −0.1197 | 0.087* | |
| H9C | 0.5777 | 0.3812 | −0.1049 | 0.087* | |
| C6 | 0.8398 (3) | 0.0646 (2) | 0.08064 (8) | 0.0592 (4) | |
| H6A | 0.8267 | 0.0649 | 0.0332 | 0.071* | |
| C2 | 0.6989 (3) | 0.1453 (2) | 0.18648 (7) | 0.0586 (4) | |
| C5 | 1.0271 (3) | −0.0222 (2) | 0.11457 (10) | 0.0708 (5) | |
| H5A | 1.1397 | −0.0794 | 0.0900 | 0.085* | |
| C3 | 0.8824 (4) | 0.0594 (2) | 0.22135 (9) | 0.0756 (5) | |
| H3A | 0.8947 | 0.0580 | 0.2688 | 0.091* | |
| C4 | 1.0489 (3) | −0.0250 (2) | 0.18462 (10) | 0.0756 (5) | |
| H4A | 1.1760 | −0.0839 | 0.2072 | 0.091* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N2 | 0.0448 (6) | 0.0508 (6) | 0.0460 (6) | 0.0032 (5) | −0.0023 (5) | 0.0011 (5) |
| O1 | 0.0518 (6) | 0.0700 (7) | 0.0507 (6) | 0.0133 (5) | −0.0049 (4) | 0.0030 (5) |
| N1 | 0.0475 (6) | 0.0591 (7) | 0.0447 (6) | 0.0106 (5) | 0.0006 (5) | 0.0019 (5) |
| C1 | 0.0475 (7) | 0.0482 (7) | 0.0471 (7) | −0.0069 (6) | −0.0046 (5) | 0.0041 (5) |
| C8 | 0.0434 (7) | 0.0520 (7) | 0.0455 (7) | −0.0015 (6) | −0.0035 (5) | −0.0004 (5) |
| C7 | 0.0482 (7) | 0.0490 (7) | 0.0455 (7) | −0.0010 (6) | 0.0006 (5) | −0.0021 (5) |
| F1 | 0.0899 (8) | 0.1230 (10) | 0.0462 (5) | 0.0075 (6) | 0.0006 (5) | −0.0129 (5) |
| C9 | 0.0538 (8) | 0.0733 (10) | 0.0478 (7) | 0.0058 (7) | 0.0039 (6) | 0.0000 (7) |
| C6 | 0.0601 (9) | 0.0623 (9) | 0.0545 (8) | 0.0069 (7) | −0.0007 (6) | 0.0061 (7) |
| C2 | 0.0588 (9) | 0.0683 (10) | 0.0475 (7) | −0.0101 (7) | −0.0058 (6) | 0.0002 (6) |
| C5 | 0.0599 (10) | 0.0664 (11) | 0.0850 (12) | 0.0100 (8) | −0.0034 (8) | 0.0118 (9) |
| C3 | 0.0764 (11) | 0.0912 (13) | 0.0558 (9) | −0.0153 (10) | −0.0222 (8) | 0.0153 (8) |
| C4 | 0.0619 (10) | 0.0734 (12) | 0.0880 (12) | −0.0051 (8) | −0.0233 (9) | 0.0253 (10) |
| N2—C7 | 1.2732 (18) | C9—H9A | 0.9600 |
| N2—N1 | 1.3775 (16) | C9—H9B | 0.9600 |
| O1—C8 | 1.2269 (17) | C9—H9C | 0.9600 |
| N1—C8 | 1.3529 (17) | C6—C5 | 1.376 (2) |
| N1—H1A | 0.8600 | C6—H6A | 0.9300 |
| C1—C2 | 1.3809 (19) | C2—C3 | 1.366 (2) |
| C1—C6 | 1.394 (2) | C5—C4 | 1.375 (3) |
| C1—C7 | 1.4595 (19) | C5—H5A | 0.9300 |
| C8—C9 | 1.494 (2) | C3—C4 | 1.379 (3) |
| C7—H7A | 0.9300 | C3—H3A | 0.9300 |
| F1—C2 | 1.363 (2) | C4—H4A | 0.9300 |
| C7—N2—N1 | 114.63 (11) | H9A—C9—H9C | 109.5 |
| C8—N1—N2 | 121.75 (11) | H9B—C9—H9C | 109.5 |
| C8—N1—H1A | 119.1 | C5—C6—C1 | 121.01 (15) |
| N2—N1—H1A | 119.1 | C5—C6—H6A | 119.5 |
| C2—C1—C6 | 116.37 (14) | C1—C6—H6A | 119.5 |
| C2—C1—C7 | 120.46 (13) | F1—C2—C3 | 118.90 (14) |
| C6—C1—C7 | 123.17 (12) | F1—C2—C1 | 117.35 (14) |
| O1—C8—N1 | 119.12 (13) | C3—C2—C1 | 123.74 (16) |
| O1—C8—C9 | 122.79 (13) | C4—C5—C6 | 120.45 (17) |
| N1—C8—C9 | 118.08 (12) | C4—C5—H5A | 119.8 |
| N2—C7—C1 | 120.89 (13) | C6—C5—H5A | 119.8 |
| N2—C7—H7A | 119.6 | C2—C3—C4 | 118.43 (16) |
| C1—C7—H7A | 119.6 | C2—C3—H3A | 120.8 |
| C8—C9—H9A | 109.5 | C4—C3—H3A | 120.8 |
| C8—C9—H9B | 109.5 | C5—C4—C3 | 120.00 (16) |
| H9A—C9—H9B | 109.5 | C5—C4—H4A | 120.0 |
| C8—C9—H9C | 109.5 | C3—C4—H4A | 120.0 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O1i | 0.86 | 2.08 | 2.915 (2) | 163 |
| Symmetry code: (i) −x, −y+1, −z. |
Experimental details
| Crystal data | |
| Chemical formula | C9H9FN2O |
| Mr | 180.18 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 293 |
| a, b, c (Å) | 5.3227 (11), 8.4603 (17), 19.656 (4) |
| β (°) | 93.70 (3) |
| V (Å3) | 883.3 (3) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.11 |
| Crystal size (mm) | 0.30 × 0.30 × 0.20 |
| Data collection | |
| Diffractometer | Bruker SMART CCD diffractometer |
| Absorption correction | – |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 7687, 2010, 1515 |
| Rint | 0.036 |
| (sin θ/λ)max (Å−1) | 0.649 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.128, 1.04 |
| No. of reflections | 2010 |
| No. of parameters | 119 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.14, −0.21 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O1i | 0.86 | 2.08 | 2.915 (2) | 163 |
| Symmetry code: (i) −x, −y+1, −z. |
Acknowledgements
The authors would like to thank the National Natural Science Foundation of Shandong Province (Y2008B29) and Yuandu Scholar of Weifang City for support.
References
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145–153. CrossRef CAS Web of Science Google Scholar
Girgis, A. S. (2006). J. Chem. Res. pp. 81–85. CrossRef Google Scholar
Li, Y.-F. & Jian, F.-F. (2008). Acta Cryst. E64, o2409. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
Schiff bases have important applications in analytical chemistry (Cimerman et al., 1997). As part of our search for new Schiff bases with similar applications, we synthesized the title compound, (I), and report its crystal structure herein (Fig. 1).
All the bond lengths and angles in (I) are within normal ranges (Li & Jian, 2008). The C7=N2 bond length of 1.2732 (18)Å is slight shorter than the C=N double bond [1.281 (2) Å] reported (Girgis, 2006) in a related compound.
In the crystal structure, adjacent molecules are linked into a centro-symmetric supra-molecular dimer by intermolecular N—H···O hydrogen bonding (Table 1).