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  • NCHFNOIn the title compound, CHFNO, the pyridine ring is connected to a benzene ring by a -CH-NH- chain. The nitro group is twisted out of the pyridine ring plane [torsion angle O-N-C-C = 10.41 (10)°]. An intramolecular N-H⋯O hydrogen bond occurs. The fluoro­benzene ring is disordered over two positions [occupancy ratio = 0.59 (3):0.41 (3)]. Inter­molecular N-H⋯O and N-H⋯N hydrogen bonds stabilize the crystal structure. Related literature The title compound is an inter­mediate in the synthesis of analgesic drugs. For the analgesic properties of flupirtine (systematic name eth­yl{2-amino-6-[(4-fluoro­benz­yl)amino]­pyridin-3-yl}carbamate), see: Klawe & Maschke (2009 ▶). For synthetic procedures, see: Gerhard & Ilia (2010 ▶). For a related structure, see: Wang (2009 ▶). Experimental Crystal data CHFNO M = 262.25 Monoclinic, inline-formula a = 14.8187 (14) Å b = 5.9972 (6) Å c = 14.8840 (15) Å β = 109.827 (1)° V = 1244.3 (2) Å Z = 4 Mo Kα radiation μ = 0.11 mm T = 298 K 0.38 × 0.15 × 0.11 mm Data collection Rigaku SCXmini CCD diffractometer Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T = 0.960, T = 0.988 5923 measured reflections 2184 independent reflections 1169 reflections with I > 2σ(I) R = 0.056 Refinement R[F > 2σ(F )] = 0.052 wR(F ) = 0.140 S = 1.03 2184 reflections 227 parameters H-atom parameters constrained Δρ = 0.21 e Å Δρ = −0.22 e Å Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97. Supplementary Material Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018642/pv2411sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018642/pv2411Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811018642/pv2411Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report Hydrogen-bond geometry (Å, °) Symmetry codes: (i) inline-formula ; (ii) inline-formula .
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