organic compounds
4-{[(5-Methyl-2-furyl)methylene]hydrazinocarbonyl}pyridinium chloride monohydrate
aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and bMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
*Correspondence e-mail: ffjian2008@163.com
The title compound, C12H12N3O2+·Cl−·H2O, was prepared by the reaction of N′-[(5-methyl-2-furyl)methylene]isonicotinohydrazide and hydrochloric acid at room temperature. The entire molecule is approximately planar with a maximum deviation of 0.047 (2) Å. An intramolecular C—H⋯O interaction is observed. O—H⋯Cl, N—H⋯Cl, N—H⋯O, N—H⋯N, C—H⋯Cl and C—H⋯O hydrogen-bonds stabilize the crystal structure.
Related literature
et al. (2005). For their antimicrobial and anticancer applications, see: Tarafder et al. (2000) and Deschamps et al. (2003), respectively.
have been used extensively as ligands in the field of coordination chemistry, see: CuiExperimental
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
10.1107/S1600536809028426/at2845sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809028426/at2845Isup2.hkl
A mixture of N'-[(5-methyl-2-furyl)methylene]isonicotinohydrazide (0.02 mol) and hydrochloric acid (0.01 mol) was stirred with ethanol (50 ml) at 298 K for 2 h, then afford the title compound (2.61 g, yield 92%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol and trichloromethane (1:1) at room temperature.
The H atoms of the water molecule were found from a difference Fourier map and refined freely. The other H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H and N—H distances of 0.93–0.96 and 0.86 Å, and with Uiso = 1.2–1.5Ueq(C,N).
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.Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
C12H12N3O2+·Cl−·H2O | F(000) = 592 |
Mr = 283.71 | Dx = 1.348 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2715 reflections |
a = 8.5258 (17) Å | θ = 3.1–27.5° |
b = 14.435 (3) Å | µ = 0.28 mm−1 |
c = 13.625 (4) Å | T = 293 K |
β = 123.55 (2)° | Bar, yellow |
V = 1397.5 (7) Å3 | 0.20 × 0.15 × 0.11 mm |
Z = 4 |
Bruker P4 diffractometer | 2715 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 27.5°, θmin = 3.1° |
Detector resolution: 3 pixels mm-1 | h = −10→11 |
ω scans | k = −18→18 |
13328 measured reflections | l = −17→17 |
3187 independent 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0543P)2 + 0.3029P] where P = (Fo2 + 2Fc2)/3 |
3187 reflections | (Δ/σ)max < 0.001 |
180 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C12H12N3O2+·Cl−·H2O | V = 1397.5 (7) Å3 |
Mr = 283.71 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.5258 (17) Å | µ = 0.28 mm−1 |
b = 14.435 (3) Å | T = 293 K |
c = 13.625 (4) Å | 0.20 × 0.15 × 0.11 mm |
β = 123.55 (2)° |
Bruker P4 diffractometer | 2715 reflections with I > 2σ(I) |
13328 measured reflections | Rint = 0.026 |
3187 independent reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.27 e Å−3 |
3187 reflections | Δρmin = −0.21 e Å−3 |
180 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 | ||
Cl1 | 0.22892 (6) | −0.42533 (3) | −0.18006 (4) | 0.06023 (16) | |
O1 | 0.51022 (13) | 0.04123 (6) | 0.13453 (8) | 0.0380 (2) | |
O2 | 0.05971 (14) | −0.22008 (7) | −0.02944 (10) | 0.0536 (3) | |
N1 | 0.16922 (14) | −0.04732 (7) | −0.03026 (9) | 0.0327 (2) | |
N2 | −0.00554 (14) | −0.08118 (7) | −0.11953 (9) | 0.0327 (2) | |
H2A | −0.0844 | −0.0467 | −0.1778 | 0.039* | |
N3 | −0.57485 (15) | −0.28167 (8) | −0.36865 (9) | 0.0392 (3) | |
H3A | −0.6822 | −0.3057 | −0.4198 | 0.047* | |
C1 | 0.8247 (2) | 0.07121 (14) | 0.30399 (16) | 0.0616 (5) | |
H1B | 0.9141 | 0.1209 | 0.3397 | 0.092* | |
H1C | 0.8779 | 0.0215 | 0.2847 | 0.092* | |
H1D | 0.7941 | 0.0493 | 0.3580 | 0.092* | |
C2 | 0.65193 (19) | 0.10503 (11) | 0.19547 (13) | 0.0419 (3) | |
C3 | 0.5985 (2) | 0.18739 (10) | 0.14057 (14) | 0.0469 (4) | |
H3B | 0.6695 | 0.2415 | 0.1641 | 0.056* | |
C4 | 0.4137 (2) | 0.17617 (10) | 0.04032 (13) | 0.0441 (3) | |
H4A | 0.3395 | 0.2216 | −0.0145 | 0.053* | |
C5 | 0.36538 (19) | 0.08648 (9) | 0.03927 (12) | 0.0354 (3) | |
C6 | 0.19437 (19) | 0.03842 (9) | −0.04240 (11) | 0.0359 (3) | |
H6A | 0.0978 | 0.0707 | −0.1067 | 0.043* | |
C7 | −0.04668 (16) | −0.16914 (9) | −0.11160 (10) | 0.0321 (3) | |
C8 | −0.23608 (16) | −0.20547 (8) | −0.20798 (10) | 0.0301 (3) | |
C9 | −0.37266 (17) | −0.15335 (9) | −0.30253 (11) | 0.0365 (3) | |
H9A | −0.3495 | −0.0920 | −0.3115 | 0.044* | |
C10 | −0.54274 (18) | −0.19394 (10) | −0.38265 (11) | 0.0404 (3) | |
H10A | −0.6356 | −0.1601 | −0.4468 | 0.049* | |
C11 | −0.4484 (2) | −0.33342 (10) | −0.27924 (13) | 0.0441 (3) | |
H11A | −0.4768 | −0.3942 | −0.2721 | 0.053* | |
C12 | −0.27438 (19) | −0.29683 (9) | −0.19686 (12) | 0.0413 (3) | |
H12A | −0.1837 | −0.3330 | −0.1346 | 0.050* | |
O1W | −0.3179 (3) | −0.06393 (18) | −0.5308 (2) | 0.1060 (7) | |
H2W1 | −0.282 (4) | −0.0189 (19) | −0.481 (2) | 0.093 (8)* | |
H1W1 | −0.419 (4) | −0.0676 (18) | −0.566 (2) | 0.084 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0599 (3) | 0.0341 (2) | 0.0513 (2) | −0.00819 (16) | 0.00847 (19) | −0.00564 (15) |
O1 | 0.0337 (5) | 0.0317 (5) | 0.0423 (5) | −0.0068 (4) | 0.0170 (4) | −0.0055 (4) |
O2 | 0.0291 (5) | 0.0402 (5) | 0.0497 (6) | −0.0051 (4) | −0.0044 (4) | 0.0125 (5) |
N1 | 0.0253 (5) | 0.0331 (5) | 0.0312 (5) | −0.0053 (4) | 0.0104 (4) | −0.0060 (4) |
N2 | 0.0240 (5) | 0.0305 (5) | 0.0292 (5) | −0.0022 (4) | 0.0056 (4) | −0.0012 (4) |
N3 | 0.0252 (5) | 0.0466 (7) | 0.0317 (5) | −0.0085 (5) | 0.0070 (4) | −0.0110 (5) |
C1 | 0.0368 (8) | 0.0758 (12) | 0.0565 (10) | −0.0073 (8) | 0.0159 (7) | −0.0122 (9) |
C2 | 0.0348 (6) | 0.0454 (7) | 0.0472 (8) | −0.0143 (6) | 0.0236 (6) | −0.0167 (6) |
C3 | 0.0515 (8) | 0.0396 (7) | 0.0572 (9) | −0.0204 (7) | 0.0348 (7) | −0.0155 (7) |
C4 | 0.0531 (8) | 0.0334 (7) | 0.0484 (8) | −0.0089 (6) | 0.0297 (7) | −0.0025 (6) |
C5 | 0.0377 (7) | 0.0321 (6) | 0.0359 (6) | −0.0053 (5) | 0.0200 (6) | −0.0047 (5) |
C6 | 0.0348 (6) | 0.0332 (6) | 0.0335 (6) | −0.0030 (5) | 0.0151 (5) | −0.0032 (5) |
C7 | 0.0221 (5) | 0.0321 (6) | 0.0305 (6) | −0.0002 (5) | 0.0072 (5) | −0.0007 (5) |
C8 | 0.0217 (5) | 0.0319 (6) | 0.0282 (5) | −0.0003 (5) | 0.0084 (5) | −0.0021 (5) |
C9 | 0.0278 (6) | 0.0365 (6) | 0.0326 (6) | −0.0007 (5) | 0.0089 (5) | 0.0038 (5) |
C10 | 0.0262 (6) | 0.0476 (8) | 0.0302 (6) | 0.0008 (6) | 0.0047 (5) | 0.0022 (5) |
C11 | 0.0386 (7) | 0.0333 (7) | 0.0435 (7) | −0.0094 (6) | 0.0120 (6) | −0.0066 (6) |
C12 | 0.0319 (6) | 0.0307 (6) | 0.0384 (7) | −0.0011 (5) | 0.0050 (5) | 0.0010 (5) |
O1W | 0.0743 (12) | 0.152 (2) | 0.0905 (13) | −0.0102 (12) | 0.0446 (11) | −0.0516 (13) |
O1—C5 | 1.3655 (17) | C3—H3B | 0.9300 |
O1—C2 | 1.3742 (16) | C4—C5 | 1.3566 (19) |
O2—C7 | 1.2225 (16) | C4—H4A | 0.9300 |
N1—C6 | 1.2823 (17) | C5—C6 | 1.4324 (18) |
N1—N2 | 1.3911 (14) | C6—H6A | 0.9300 |
N2—C7 | 1.3375 (16) | C7—C8 | 1.5044 (16) |
N2—H2A | 0.8600 | C8—C12 | 1.3868 (18) |
N3—C11 | 1.3239 (18) | C8—C9 | 1.3869 (17) |
N3—C10 | 1.3314 (19) | C9—C10 | 1.3741 (18) |
N3—H3A | 0.8600 | C9—H9A | 0.9300 |
C1—C2 | 1.479 (2) | C10—H10A | 0.9300 |
C1—H1B | 0.9600 | C11—C12 | 1.3780 (18) |
C1—H1C | 0.9600 | C11—H11A | 0.9300 |
C1—H1D | 0.9600 | C12—H12A | 0.9300 |
C2—C3 | 1.343 (2) | O1W—H2W1 | 0.87 (3) |
C3—C4 | 1.412 (2) | O1W—H1W1 | 0.72 (3) |
C5—O1—C2 | 106.56 (11) | C4—C5—C6 | 130.05 (13) |
C6—N1—N2 | 113.64 (11) | O1—C5—C6 | 120.28 (11) |
C7—N2—N1 | 117.70 (10) | N1—C6—C5 | 122.56 (12) |
C7—N2—H2A | 121.1 | N1—C6—H6A | 118.7 |
N1—N2—H2A | 121.1 | C5—C6—H6A | 118.7 |
C11—N3—C10 | 122.76 (11) | O2—C7—N2 | 123.37 (11) |
C11—N3—H3A | 118.6 | O2—C7—C8 | 119.01 (11) |
C10—N3—H3A | 118.6 | N2—C7—C8 | 117.61 (10) |
C2—C1—H1B | 109.5 | C12—C8—C9 | 119.33 (11) |
C2—C1—H1C | 109.5 | C12—C8—C7 | 116.11 (11) |
H1B—C1—H1C | 109.5 | C9—C8—C7 | 124.53 (11) |
C2—C1—H1D | 109.5 | C10—C9—C8 | 118.83 (13) |
H1B—C1—H1D | 109.5 | C10—C9—H9A | 120.6 |
H1C—C1—H1D | 109.5 | C8—C9—H9A | 120.6 |
C3—C2—O1 | 110.02 (13) | N3—C10—C9 | 120.13 (12) |
C3—C2—C1 | 133.87 (14) | N3—C10—H10A | 119.9 |
O1—C2—C1 | 116.11 (14) | C9—C10—H10A | 119.9 |
C2—C3—C4 | 106.92 (13) | N3—C11—C12 | 119.73 (13) |
C2—C3—H3B | 126.5 | N3—C11—H11A | 120.1 |
C4—C3—H3B | 126.5 | C12—C11—H11A | 120.1 |
C5—C4—C3 | 106.83 (14) | C11—C12—C8 | 119.21 (12) |
C5—C4—H4A | 126.6 | C11—C12—H12A | 120.4 |
C3—C4—H4A | 126.6 | C8—C12—H12A | 120.4 |
C4—C5—O1 | 109.67 (12) | H2W1—O1W—H1W1 | 111 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H2W1···Cl1i | 0.86 (3) | 2.40 (3) | 3.229 (3) | 162 (3) |
O1W—H1W1···Cl1ii | 0.72 (3) | 2.51 (3) | 3.225 (3) | 177 (2) |
N2—H2A···Cl1i | 0.86 | 2.39 | 3.2243 (15) | 164 |
N3—H3A···O2ii | 0.86 | 1.89 | 2.639 (2) | 144 |
N3—H3A···N1ii | 0.86 | 2.50 | 3.2238 (18) | 142 |
C3—H3B···Cl1iii | 0.93 | 2.76 | 3.6574 (19) | 162 |
C6—H6A···Cl1i | 0.93 | 2.69 | 3.5374 (18) | 151 |
C9—H9A···Cl1i | 0.93 | 2.64 | 3.5656 (18) | 171 |
C11—H11A···O1ii | 0.93 | 2.45 | 3.1694 (19) | 135 |
C12—H12A···O2 | 0.93 | 2.39 | 2.713 (2) | 100 |
Symmetry codes: (i) −x, y+1/2, −z−1/2; (ii) x−1, −y−1/2, z−1/2; (iii) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C12H12N3O2+·Cl−·H2O |
Mr | 283.71 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 8.5258 (17), 14.435 (3), 13.625 (4) |
β (°) | 123.55 (2) |
V (Å3) | 1397.5 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.28 |
Crystal size (mm) | 0.20 × 0.15 × 0.11 |
Data collection | |
Diffractometer | Bruker P4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13328, 3187, 2715 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.107, 1.07 |
No. of reflections | 3187 |
No. of parameters | 180 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.21 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008.
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H2W1···Cl1i | 0.86 (3) | 2.40 (3) | 3.229 (3) | 162 (3) |
O1W—H1W1···Cl1ii | 0.72 (3) | 2.51 (3) | 3.225 (3) | 177 (2) |
N2—H2A···Cl1i | 0.8600 | 2.3900 | 3.2243 (15) | 164.00 |
N3—H3A···O2ii | 0.8600 | 1.8900 | 2.639 (2) | 144.00 |
N3—H3A···N1ii | 0.8600 | 2.5000 | 3.2238 (18) | 142.00 |
C3—H3B···Cl1iii | 0.9300 | 2.7600 | 3.6574 (19) | 162.00 |
C6—H6A···Cl1i | 0.9300 | 2.6900 | 3.5374 (18) | 151.00 |
C9—H9A···Cl1i | 0.9300 | 2.6400 | 3.5656 (18) | 171.00 |
C11—H11A···O1ii | 0.9300 | 2.4500 | 3.1694 (19) | 135.00 |
C12—H12A···O2 | 0.9300 | 2.3900 | 2.713 (2) | 100.00 |
Symmetry codes: (i) −x, y+1/2, −z−1/2; (ii) x−1, −y−1/2, z−1/2; (iii) −x+1, −y, −z. |
Acknowledgements
The authors would like to thank the Natural Science Foundation of Shandong Province (No.Y2008B30).
References
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cui, S.-L., Zhou, F.-Y. & Lin, X.-F. (2005). Acta Cryst. E61, o3198–o3199. Web of Science CSD CrossRef IUCr Journals Google Scholar
Deschamps, P., Kulkarni, P. P. & Sarkar, B. (2003). Inorg. Chem. 42, 7366–7368. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tarafder, M. T. H., Ali, M. A., Wee, D. J., Azahari, K., Silong, S. & Crouse, K. A. (2000). Transition Met. Chem. 25, 456–460. Web of Science CrossRef CAS Google Scholar
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Schiff bases have been used extensively as ligands in the field of coordination chemistry (Cui et al., 2005). And they have antimicrobial (Tarafder et al., 2000) and anticancer applications (Deschamps et al., 2003). The title compound (I) was synthesized and we report its crystal structure here.
In the crystal structure of (I) (Fig. 1), the carbon and nitrogen atoms are nearly the same plane with a maximum deviation of 0.047Å for N2. There are intra- and intermolecular O—H···Cl, N—H···Cl, N—H···O, N—H···N, C—H···Cl and C—H···O hydrogen-bonds to stabilize the crystal structure (Table 1).