Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054062/ci2498sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054062/ci2498Isup2.hkl |
CCDC reference: 672795
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.065
- wR factor = 0.137
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT480_ALERT_4_C Long H...A H-Bond Reported H5A .. F17 .. 2.56 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
2-[3-(Trifluoromethyl)phenyl]furo[3,2-c]pyridine was prepared by five step synthesis according to literature procedures of Gajdoš et al. (2006) and Bradiaková et al. (2008).
All H atoms were placed in geometrically calculated positions and allowed to ride on their parent atoms, with C—H distances of 0.93 Å and Uiso set at 1.2Ueq of the parent atom.
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: enCIFer (Allen et al., 2004).
C14H8F3NO | F(000) = 536 |
Mr = 263.21 | Dx = 1.523 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9171 reflections |
a = 13.4075 (16) Å | θ = 3.3–29.4° |
b = 12.1237 (9) Å | µ = 0.13 mm−1 |
c = 7.3008 (10) Å | T = 298 K |
β = 104.754 (13)° | Needle, colourless |
V = 1147.6 (2) Å3 | 0.51 × 0.17 × 0.02 mm |
Z = 4 |
Oxford Diffraction Gemini R CCD diffractometer | 2335 independent reflections |
Radiation source: fine-focus sealed tube | 1185 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
Detector resolution: 10.4340 pixels mm-1 | θmax = 26.4°, θmin = 4.4° |
Rotation method data acquisition using ω and ϕ scans | h = −16→16 |
Absorption correction: analytical (Clark & Reid, 1995) | k = −15→15 |
Tmin = 0.960, Tmax = 0.997 | l = −9→9 |
32658 measured reflections |
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)] = 0.065 | H-atom parameters constrained |
wR(F2) = 0.137 | w = 1/[σ2(Fo2) + (0.0009P)2 + 2.196P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
2335 reflections | Δρmax = 0.21 e Å−3 |
173 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0070 (4) |
C14H8F3NO | V = 1147.6 (2) Å3 |
Mr = 263.21 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.4075 (16) Å | µ = 0.13 mm−1 |
b = 12.1237 (9) Å | T = 298 K |
c = 7.3008 (10) Å | 0.51 × 0.17 × 0.02 mm |
β = 104.754 (13)° |
Oxford Diffraction Gemini R CCD diffractometer | 2335 independent reflections |
Absorption correction: analytical (Clark & Reid, 1995) | 1185 reflections with I > 2σ(I) |
Tmin = 0.960, Tmax = 0.997 | Rint = 0.058 |
32658 measured reflections |
R[F2 > 2σ(F2)] = 0.065 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.21 e Å−3 |
2335 reflections | Δρmin = −0.20 e Å−3 |
173 parameters |
Experimental. face-indexed (CrysAlis RED; Oxford Diffraction, 2006) |
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 | ||
C2 | 0.6800 (4) | 0.6145 (3) | 0.1799 (7) | 0.0839 (14) | |
H2A | 0.7327 | 0.6565 | 0.1537 | 0.101* | |
C3 | 0.5935 (4) | 0.6607 (4) | 0.2109 (8) | 0.0884 (15) | |
H3A | 0.5884 | 0.7372 | 0.2030 | 0.106* | |
C5 | 0.5215 (3) | 0.4974 (4) | 0.2603 (7) | 0.0748 (12) | |
H5A | 0.4677 | 0.4578 | 0.2881 | 0.090* | |
C6 | 0.6366 (3) | 0.3280 (3) | 0.2264 (6) | 0.0625 (11) | |
H6A | 0.5994 | 0.2664 | 0.2463 | 0.075* | |
C7 | 0.7296 (3) | 0.3280 (3) | 0.1896 (5) | 0.0551 (10) | |
C8 | 0.6841 (3) | 0.5019 (3) | 0.1900 (6) | 0.0636 (11) | |
C9 | 0.6055 (3) | 0.4405 (3) | 0.2292 (6) | 0.0595 (10) | |
C10 | 0.8025 (3) | 0.2409 (3) | 0.1813 (5) | 0.0540 (10) | |
C11 | 0.7755 (3) | 0.1315 (3) | 0.2039 (5) | 0.0583 (10) | |
H11A | 0.7107 | 0.1150 | 0.2205 | 0.070* | |
C12 | 0.8443 (3) | 0.0486 (3) | 0.2016 (6) | 0.0600 (11) | |
C13 | 0.9415 (3) | 0.0716 (4) | 0.1779 (6) | 0.0699 (12) | |
H13A | 0.9881 | 0.0147 | 0.1790 | 0.084* | |
C14 | 0.9688 (3) | 0.1781 (4) | 0.1528 (6) | 0.0713 (12) | |
H14A | 1.0335 | 0.1936 | 0.1345 | 0.086* | |
C15 | 0.8995 (3) | 0.2631 (3) | 0.1548 (6) | 0.0633 (11) | |
H15A | 0.9183 | 0.3355 | 0.1383 | 0.076* | |
C16 | 0.8184 (4) | −0.0687 (4) | 0.2311 (8) | 0.0783 (13) | |
N4 | 0.5155 (3) | 0.6069 (3) | 0.2514 (6) | 0.0838 (11) | |
O1 | 0.7619 (2) | 0.4357 (2) | 0.1668 (4) | 0.0671 (8) | |
F17 | 0.7194 (2) | −0.0846 (2) | 0.2133 (6) | 0.1261 (14) | |
F18 | 0.8665 (3) | −0.1046 (2) | 0.4027 (5) | 0.1156 (11) | |
F19 | 0.8467 (2) | −0.1372 (2) | 0.1143 (5) | 0.1072 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.086 (3) | 0.044 (2) | 0.132 (4) | −0.004 (2) | 0.045 (3) | −0.002 (3) |
C3 | 0.094 (4) | 0.047 (2) | 0.133 (5) | 0.003 (3) | 0.044 (3) | −0.003 (3) |
C5 | 0.067 (3) | 0.056 (3) | 0.104 (3) | −0.001 (2) | 0.027 (3) | −0.001 (3) |
C6 | 0.061 (3) | 0.045 (2) | 0.081 (3) | −0.0037 (19) | 0.018 (2) | 0.003 (2) |
C7 | 0.058 (3) | 0.041 (2) | 0.065 (3) | −0.0053 (18) | 0.014 (2) | 0.0015 (18) |
C8 | 0.065 (3) | 0.045 (2) | 0.083 (3) | −0.005 (2) | 0.025 (2) | −0.006 (2) |
C9 | 0.059 (2) | 0.048 (2) | 0.073 (3) | 0.002 (2) | 0.019 (2) | 0.003 (2) |
C10 | 0.051 (2) | 0.050 (2) | 0.059 (2) | −0.0002 (18) | 0.0107 (19) | −0.0034 (18) |
C11 | 0.054 (2) | 0.051 (2) | 0.070 (3) | 0.0008 (19) | 0.015 (2) | 0.001 (2) |
C12 | 0.056 (2) | 0.049 (2) | 0.073 (3) | 0.0077 (19) | 0.013 (2) | 0.001 (2) |
C13 | 0.058 (3) | 0.063 (3) | 0.091 (3) | 0.013 (2) | 0.023 (2) | 0.000 (2) |
C14 | 0.055 (3) | 0.071 (3) | 0.091 (3) | −0.001 (2) | 0.023 (2) | −0.001 (2) |
C15 | 0.060 (3) | 0.052 (2) | 0.078 (3) | −0.002 (2) | 0.019 (2) | 0.001 (2) |
C16 | 0.071 (3) | 0.061 (3) | 0.106 (4) | 0.013 (2) | 0.029 (3) | 0.002 (3) |
N4 | 0.088 (3) | 0.052 (2) | 0.116 (3) | 0.012 (2) | 0.034 (2) | 0.001 (2) |
O1 | 0.0642 (17) | 0.0433 (15) | 0.099 (2) | −0.0034 (13) | 0.0309 (16) | 0.0001 (14) |
F17 | 0.0762 (19) | 0.0539 (16) | 0.258 (4) | −0.0001 (14) | 0.061 (2) | 0.012 (2) |
F18 | 0.147 (3) | 0.080 (2) | 0.120 (3) | 0.0169 (19) | 0.035 (2) | 0.0299 (18) |
F19 | 0.125 (2) | 0.0591 (16) | 0.148 (3) | 0.0073 (16) | 0.055 (2) | −0.0197 (17) |
C2—C3 | 1.357 (6) | C10—C11 | 1.395 (5) |
C2—C8 | 1.368 (5) | C10—C15 | 1.389 (5) |
C2—H2A | 0.93 | C11—C12 | 1.367 (5) |
C3—N4 | 1.329 (6) | C11—H11A | 0.93 |
C3—H3A | 0.93 | C12—C13 | 1.385 (5) |
C5—N4 | 1.331 (5) | C12—C16 | 1.493 (6) |
C5—C9 | 1.388 (5) | C13—C14 | 1.366 (6) |
C5—H5A | 0.93 | C13—H13A | 0.93 |
C6—C7 | 1.341 (5) | C14—C15 | 1.390 (5) |
C6—C9 | 1.428 (5) | C14—H14A | 0.93 |
C6—H6A | 0.93 | C15—H15A | 0.93 |
C7—O1 | 1.399 (4) | C16—F17 | 1.314 (5) |
C7—C10 | 1.451 (5) | C16—F19 | 1.313 (5) |
C8—O1 | 1.360 (4) | C16—F18 | 1.328 (5) |
C8—C9 | 1.378 (5) | ||
C3—C2—C8 | 115.3 (4) | C12—C11—C10 | 120.1 (4) |
C3—C2—H2A | 122.4 | C12—C11—H11A | 120.0 |
C8—C2—H2A | 122.4 | C10—C11—H11A | 120.0 |
N4—C3—C2 | 126.1 (4) | C11—C12—C13 | 120.8 (4) |
N4—C3—H3A | 117.0 | C11—C12—C16 | 121.1 (4) |
C2—C3—H3A | 117.0 | C13—C12—C16 | 118.1 (4) |
N4—C5—C9 | 121.9 (4) | C14—C13—C12 | 120.0 (4) |
N4—C5—H5A | 119.0 | C14—C13—H13A | 120.0 |
C9—C5—H5A | 119.0 | C12—C13—H13A | 120.0 |
C7—C6—C9 | 107.0 (3) | C13—C14—C15 | 119.8 (4) |
C7—C6—H6A | 126.5 | C13—C14—H14A | 120.1 |
C9—C6—H6A | 126.5 | C15—C14—H14A | 120.1 |
C6—C7—O1 | 110.8 (3) | C14—C15—C10 | 120.6 (4) |
C6—C7—C10 | 132.8 (4) | C14—C15—H15A | 119.7 |
O1—C7—C10 | 116.3 (3) | C10—C15—H15A | 119.7 |
O1—C8—C9 | 111.0 (3) | F17—C16—F19 | 107.1 (4) |
O1—C8—C2 | 127.1 (4) | F17—C16—F18 | 106.3 (4) |
C9—C8—C2 | 121.9 (4) | F19—C16—F18 | 104.7 (4) |
C8—C9—C5 | 117.4 (4) | F17—C16—C12 | 113.1 (4) |
C8—C9—C6 | 105.8 (3) | F19—C16—C12 | 113.1 (4) |
C5—C9—C6 | 136.8 (4) | F18—C16—C12 | 111.9 (4) |
C11—C10—C15 | 118.7 (4) | C3—N4—C5 | 117.4 (4) |
C11—C10—C7 | 119.3 (3) | C8—O1—C7 | 105.4 (3) |
C15—C10—C7 | 122.0 (3) | ||
C8—C2—C3—N4 | 0.9 (9) | C10—C11—C12—C16 | 178.2 (4) |
C9—C6—C7—O1 | −0.3 (5) | C11—C12—C13—C14 | −1.2 (7) |
C9—C6—C7—C10 | 175.4 (4) | C16—C12—C13—C14 | −179.2 (4) |
C3—C2—C8—O1 | −179.3 (4) | C12—C13—C14—C15 | 1.2 (7) |
C3—C2—C8—C9 | −0.1 (7) | C13—C14—C15—C10 | −0.2 (7) |
O1—C8—C9—C5 | 178.7 (4) | C11—C10—C15—C14 | −0.7 (6) |
C2—C8—C9—C5 | −0.6 (7) | C7—C10—C15—C14 | 178.1 (4) |
O1—C8—C9—C6 | −1.1 (5) | C11—C12—C16—F17 | 15.2 (7) |
C2—C8—C9—C6 | 179.6 (4) | C13—C12—C16—F17 | −166.9 (4) |
N4—C5—C9—C8 | 0.6 (7) | C11—C12—C16—F19 | 137.1 (4) |
N4—C5—C9—C6 | −179.7 (5) | C13—C12—C16—F19 | −45.0 (6) |
C7—C6—C9—C8 | 0.8 (5) | C11—C12—C16—F18 | −104.9 (5) |
C7—C6—C9—C5 | −178.9 (5) | C13—C12—C16—F18 | 73.1 (5) |
C6—C7—C10—C11 | 4.2 (7) | C2—C3—N4—C5 | −1.0 (9) |
O1—C7—C10—C11 | 179.7 (3) | C9—C5—N4—C3 | 0.2 (7) |
C6—C7—C10—C15 | −174.6 (4) | C9—C8—O1—C7 | 0.9 (5) |
O1—C7—C10—C15 | 0.9 (6) | C2—C8—O1—C7 | −179.8 (5) |
C15—C10—C11—C12 | 0.6 (6) | C6—C7—O1—C8 | −0.4 (4) |
C7—C10—C11—C12 | −178.2 (4) | C10—C7—O1—C8 | −176.8 (3) |
C10—C11—C12—C13 | 0.3 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6A···N4i | 0.93 | 2.47 | 3.397 (5) | 171 |
C5—H5A···F17ii | 0.93 | 2.56 | 3.432 (5) | 156 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H8F3NO |
Mr | 263.21 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 13.4075 (16), 12.1237 (9), 7.3008 (10) |
β (°) | 104.754 (13) |
V (Å3) | 1147.6 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.51 × 0.17 × 0.02 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini R CCD diffractometer |
Absorption correction | Analytical (Clark & Reid, 1995) |
Tmin, Tmax | 0.960, 0.997 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 32658, 2335, 1185 |
Rint | 0.058 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.137, 1.03 |
No. of reflections | 2335 |
No. of parameters | 173 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.20 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg, 2001), enCIFer (Allen et al., 2004).
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6A···N4i | 0.93 | 2.47 | 3.397 (5) | 171.2 |
C5—H5A···F17ii | 0.93 | 2.56 | 3.432 (5) | 156.4 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2. |
In recent years, fluorinated compounds have been very important in the pharmaceutical field. Incorporation of an F atom instead of an H atom can alter the course of the reaction as well as biological activities. Introduction of further F atoms in a CF3 group provides better lipophilicity and the compounds might be pharmacologically more interesting compared to their non-fluorinated analogues. Many heterocyclic compounds, which bear the trifluoromethyl group, possess a wide range of biological activity (Navarrete-Vazquez et al., 2006), as herbicides (Bravo et al., 1994), fungicides (Jung et al., 2002) and inhibitors for platelet aggregation (Kücükgüzel et al., 2000). 7-(Trifluoromethyl)-quinoline derivatives have been evaluated for in vitro activity against some parasites in blood (Abadi & Brun, 2003). Furo[3,2-c]pyridine and its derivatives represent isoquinoline isosters, in which the benzene ring is replaced by the furan. The pyridine ring of this system can be readily coordinated to metal centers through N-donor atom. Structural characterization of isothiocyanate nickel(II) complexes with furo[3,2-c]pyridine and its 2-methyl, 2,3-dimethyl analogues, and [1]benzofuro[3,2-c]pyridine (Bzfupy) have been reported (Miklovič et al., 2004; Baran et al., 2005). We report here the crystal structure of the title compound, which is used as an important starting material for the synthesis of tetra-µ-acetato-bis[(benzofuro[3,2-c] pyridine)copper(II)] and bis(1-benzofuro[3,2-c]pyridine-κN) dichlorocobalt(II), the structures of which have already been reported (Vrábel et al., 2007a,b).
The molecular structure of title compound is shown in Fig. 1. The furo[3,2-c]pyridine ring system is essentially planar, with an r.m.s. deviation of 0.007 Å. The dihedral angle between the furo[3,2-c]pyridine ring system and the benzene ring is 5.5 (1)°. As can be seen from Fig. 2, the intermolecular C6—H6···N4 and C5—H5···F17 interactions (Table 1) link the molecules into layers parallel to the ab plane. Neighboring planes of molecules are connected through additional ring stacking interactions [shortest contact is C10···C15 (x, 1/2 - y, 1/2 + z), 3.370 (6) Å], resulting in a three-dimensional framework structure.