Acta Cryst. (2009). E65, o2603 [ doi:10.1107/S1600536809039002 ]
In the title compound, C16H16N2O3S·C5H5N, the benzene and thiazole rings of the Febuxostat [2-(3-cyano-4-isobutyloxy)phenyl-4-methyl-5-thiazolecarboxylic acid] molecule are almost coplanar [dihedral angle = 2.4 (1)°]. The carboxyl group is coplanar with the thiazole ring [O-C-C-C and O-C-C-S torsion angles of -0.7 (4) and 0.6 (3)°, respectively]. The pyridine molecule of crystallization is linked to the Febuxostat molecule through an O-H
N hydrogen bond. A weak ![[pi]](/logos/entities/pi_rmgif.gif)
- stacking interaction is observed between the benzene ring of the Febuxostat molecule and pyridine molecule, with a centroid-centroid distance of 3.7530 (18) Å.
2-(3-Formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester (42.6 g, 0.123 mol) was treated with formic acid (384 ml), sodium formate (15.3 g, 0.147 mol) and hydroxylamine hydrochloride (10.2 g, 0.147 mol) to give 21.4 g of 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester (yield 50.5%). Then it was hydrolyzed with NaOH in tetrahydrofuran and ethanol. Finally, brown block crystals of the title compound appropriate for X-ray data collection were obtained by slow evaporation of a pyridine solution at room temperature (yield 70%).
All H atoms were initially located from a difference Fourier map and then were regenerated at ideal positions and treated as riding, with O-H = 0.82 Å, C-H = 0.93-0.98 Å and Uiso(H) = 1.2-1.5Ueq(C,O).
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./ci2885fig1thm.gif)
| Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids. |
| C16H16N2O3S·C5H5N | Z = 2 |
| Mr = 395.47 | F(000) = 416 |
| Triclinic, P1 | Dx = 1.270 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.6040 (17) Å | Cell parameters from 25 reflections |
| b = 10.339 (2) Å | θ = 10–13° |
| c = 12.611 (3) Å | µ = 0.18 mm−1 |
| α = 82.51 (3)° | T = 296 K |
| β = 80.69 (3)° | Block, brown |
| γ = 69.61 (3)° | 0.30 × 0.20 × 0.20 mm |
| V = 1034.4 (4) Å3 |
| Enraf–Nonius CAD-4 diffractometer | 2815 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.032 |
| graphite | θmax = 25.3°, θmin = 1.6° |
| ω/2θ scans | h = 0→10 |
| Absorption correction: ψ scan (North et al., 1968) | k = −11→12 |
| Tmin = 0.947, Tmax = 0.964 | l = −14→15 |
| 4017 measured reflections | 3 standard reflections every 200 reflections |
| 3747 independent reflections | intensity decay: 1% |
| 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)] = 0.049 | H-atom parameters constrained |
| wR(F2) = 0.156 | w = 1/[σ2(Fo2) + (0.1P)2 + 0.12P] where P = (Fo2 + 2Fc2)/3 |
| S = 0.99 | (Δ/σ)max = 0.001 |
| 3747 reflections | Δρmax = 0.33 e Å−3 |
| 255 parameters | Δρmin = −0.19 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: 0.030 (5) |
| C16H16N2O3S·C5H5N | γ = 69.61 (3)° |
| Mr = 395.47 | V = 1034.4 (4) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 8.6040 (17) Å | Mo Kα radiation |
| b = 10.339 (2) Å | µ = 0.18 mm−1 |
| c = 12.611 (3) Å | T = 296 K |
| α = 82.51 (3)° | 0.30 × 0.20 × 0.20 mm |
| β = 80.69 (3)° |
| Enraf–Nonius CAD-4 diffractometer | 2815 reflections with I > 2σ(I) |
| Absorption correction: ψ scan (North et al., 1968) | Rint = 0.032 |
| Tmin = 0.947, Tmax = 0.964 | θmax = 25.3° |
| 4017 measured reflections | 3 standard reflections every 200 reflections |
| 3747 independent reflections | intensity decay: 1% |
| R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
| wR(F2) = 0.156 | Δρmax = 0.33 e Å−3 |
| S = 0.99 | Δρmin = −0.19 e Å−3 |
| 3747 reflections | Absolute structure: ? |
| 255 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| S | 0.83182 (8) | 0.26459 (7) | 0.30078 (4) | 0.0564 (2) | |
| O1 | 0.5471 (2) | 0.2112 (2) | 0.10983 (14) | 0.0754 (6) | |
| O2 | 0.7344 (2) | 0.3198 (2) | 0.08925 (14) | 0.0754 (6) | |
| H2A | 0.7091 | 0.3381 | 0.0277 | 0.113* | |
| O3 | 1.1361 (2) | 0.20514 (18) | 0.76698 (12) | 0.0586 (5) | |
| N1 | 0.6870 (3) | 0.1219 (2) | 0.43509 (15) | 0.0586 (5) | |
| N2 | 1.2786 (4) | 0.4042 (4) | 0.5613 (2) | 0.1041 (10) | |
| C1 | 0.6483 (3) | 0.2464 (3) | 0.14487 (19) | 0.0570 (6) | |
| C2 | 0.6882 (3) | 0.2095 (3) | 0.25744 (18) | 0.0523 (6) | |
| C3 | 0.7976 (3) | 0.1847 (2) | 0.42631 (17) | 0.0510 (6) | |
| C4 | 0.6240 (3) | 0.1354 (3) | 0.33987 (18) | 0.0562 (6) | |
| C5 | 0.4943 (4) | 0.0713 (3) | 0.3353 (2) | 0.0790 (9) | |
| H5A | 0.4167 | 0.1282 | 0.2874 | 0.118* | |
| H5B | 0.4357 | 0.0636 | 0.4062 | 0.118* | |
| H5C | 0.5472 | −0.0191 | 0.3096 | 0.118* | |
| C6 | 0.8868 (3) | 0.1864 (2) | 0.51606 (17) | 0.0509 (6) | |
| C7 | 0.9984 (3) | 0.2585 (3) | 0.50346 (18) | 0.0554 (6) | |
| H7A | 1.0183 | 0.3054 | 0.4374 | 0.067* | |
| C8 | 1.0807 (3) | 0.2614 (2) | 0.58894 (17) | 0.0529 (6) | |
| C9 | 1.0521 (3) | 0.1928 (2) | 0.68921 (17) | 0.0494 (5) | |
| C10 | 0.9425 (3) | 0.1192 (2) | 0.70122 (17) | 0.0539 (6) | |
| H10A | 0.9230 | 0.0714 | 0.7669 | 0.065* | |
| C11 | 0.8622 (3) | 0.1166 (3) | 0.61544 (18) | 0.0555 (6) | |
| H11A | 0.7892 | 0.0664 | 0.6247 | 0.067* | |
| C12 | 1.1917 (4) | 0.3398 (3) | 0.57499 (19) | 0.0705 (8) | |
| C13 | 1.1139 (3) | 0.1363 (3) | 0.87244 (17) | 0.0532 (6) | |
| H13A | 1.1489 | 0.0371 | 0.8677 | 0.064* | |
| H13B | 0.9971 | 0.1684 | 0.9025 | 0.064* | |
| C14 | 1.2185 (3) | 0.1690 (3) | 0.94322 (18) | 0.0555 (6) | |
| H14A | 1.3341 | 0.1432 | 0.9081 | 0.067* | |
| C15 | 1.1568 (4) | 0.3222 (3) | 0.9600 (2) | 0.0716 (7) | |
| H15A | 1.1603 | 0.3744 | 0.8914 | 0.107* | |
| H15B | 1.2270 | 0.3404 | 1.0039 | 0.107* | |
| H15C | 1.0440 | 0.3487 | 0.9952 | 0.107* | |
| C16 | 1.2148 (4) | 0.0832 (4) | 1.0511 (2) | 0.0829 (9) | |
| H16A | 1.2555 | −0.0134 | 1.0389 | 0.124* | |
| H16B | 1.1021 | 0.1077 | 1.0865 | 0.124* | |
| H16C | 1.2844 | 0.1012 | 1.0956 | 0.124* | |
| N3 | 0.6706 (3) | 0.3879 (3) | 0.89010 (17) | 0.0662 (6) | |
| C17 | 0.5872 (4) | 0.4524 (3) | 0.6832 (2) | 0.0784 (9) | |
| H17A | 0.5589 | 0.4742 | 0.6134 | 0.094* | |
| C18 | 0.6965 (4) | 0.5024 (3) | 0.7160 (2) | 0.0755 (8) | |
| H18A | 0.7444 | 0.5589 | 0.6687 | 0.091* | |
| C19 | 0.7359 (4) | 0.4686 (3) | 0.8200 (2) | 0.0702 (7) | |
| H19A | 0.8106 | 0.5035 | 0.8418 | 0.084* | |
| C20 | 0.5646 (3) | 0.3398 (3) | 0.8567 (2) | 0.0743 (8) | |
| H20A | 0.5182 | 0.2830 | 0.9048 | 0.089* | |
| C21 | 0.5200 (4) | 0.3700 (4) | 0.7544 (2) | 0.0816 (9) | |
| H21A | 0.4447 | 0.3345 | 0.7341 | 0.098* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S | 0.0649 (4) | 0.0694 (4) | 0.0399 (3) | −0.0261 (3) | −0.0190 (3) | 0.0038 (3) |
| O1 | 0.0859 (13) | 0.1005 (15) | 0.0542 (11) | −0.0423 (11) | −0.0318 (9) | 0.0028 (10) |
| O2 | 0.0786 (12) | 0.1131 (16) | 0.0442 (9) | −0.0428 (12) | −0.0256 (9) | 0.0128 (10) |
| O3 | 0.0751 (11) | 0.0709 (11) | 0.0383 (8) | −0.0323 (9) | −0.0229 (7) | 0.0072 (7) |
| N1 | 0.0607 (12) | 0.0784 (14) | 0.0422 (10) | −0.0284 (11) | −0.0138 (9) | −0.0006 (9) |
| N2 | 0.148 (3) | 0.140 (3) | 0.0683 (16) | −0.102 (2) | −0.0507 (17) | 0.0359 (16) |
| C1 | 0.0562 (14) | 0.0680 (16) | 0.0436 (12) | −0.0115 (12) | −0.0179 (11) | −0.0042 (11) |
| C2 | 0.0498 (13) | 0.0645 (15) | 0.0428 (12) | −0.0140 (11) | −0.0157 (10) | −0.0078 (10) |
| C3 | 0.0547 (13) | 0.0588 (14) | 0.0387 (12) | −0.0158 (11) | −0.0124 (10) | −0.0011 (10) |
| C4 | 0.0553 (14) | 0.0725 (16) | 0.0445 (12) | −0.0224 (12) | −0.0131 (10) | −0.0058 (11) |
| C5 | 0.0804 (19) | 0.113 (2) | 0.0605 (16) | −0.0508 (18) | −0.0194 (14) | −0.0009 (16) |
| C6 | 0.0562 (13) | 0.0583 (14) | 0.0383 (11) | −0.0164 (11) | −0.0130 (10) | −0.0027 (10) |
| C7 | 0.0665 (15) | 0.0631 (15) | 0.0382 (11) | −0.0226 (12) | −0.0155 (10) | 0.0049 (10) |
| C8 | 0.0653 (15) | 0.0591 (14) | 0.0391 (12) | −0.0249 (12) | −0.0163 (10) | 0.0034 (10) |
| C9 | 0.0599 (13) | 0.0503 (13) | 0.0378 (11) | −0.0152 (11) | −0.0148 (10) | −0.0015 (9) |
| C10 | 0.0697 (15) | 0.0583 (14) | 0.0362 (11) | −0.0240 (12) | −0.0147 (10) | 0.0053 (10) |
| C11 | 0.0658 (15) | 0.0625 (15) | 0.0448 (12) | −0.0273 (12) | −0.0150 (10) | −0.0011 (10) |
| C12 | 0.095 (2) | 0.089 (2) | 0.0439 (13) | −0.0501 (17) | −0.0309 (13) | 0.0172 (13) |
| C13 | 0.0673 (15) | 0.0578 (14) | 0.0367 (11) | −0.0214 (12) | −0.0164 (10) | 0.0025 (10) |
| C14 | 0.0565 (14) | 0.0710 (16) | 0.0400 (12) | −0.0198 (12) | −0.0142 (10) | −0.0021 (11) |
| C15 | 0.0767 (18) | 0.084 (2) | 0.0662 (16) | −0.0361 (15) | −0.0154 (14) | −0.0125 (14) |
| C16 | 0.104 (2) | 0.103 (2) | 0.0470 (14) | −0.0364 (19) | −0.0328 (15) | 0.0091 (14) |
| N3 | 0.0607 (13) | 0.0864 (16) | 0.0445 (11) | −0.0141 (12) | −0.0165 (10) | 0.0022 (10) |
| C17 | 0.0798 (19) | 0.094 (2) | 0.0447 (14) | −0.0046 (17) | −0.0231 (13) | 0.0020 (14) |
| C18 | 0.085 (2) | 0.0775 (19) | 0.0538 (15) | −0.0176 (16) | −0.0115 (14) | 0.0084 (13) |
| C19 | 0.0737 (17) | 0.0765 (18) | 0.0588 (16) | −0.0207 (15) | −0.0166 (13) | −0.0022 (13) |
| C20 | 0.0643 (17) | 0.104 (2) | 0.0547 (15) | −0.0288 (16) | −0.0183 (13) | 0.0081 (14) |
| C21 | 0.0717 (18) | 0.118 (3) | 0.0588 (16) | −0.0306 (17) | −0.0282 (14) | 0.0032 (16) |
| S—C2 | 1.714 (2) | C10—H10A | 0.93 |
| S—C3 | 1.718 (2) | C11—H11A | 0.93 |
| O1—C1 | 1.214 (3) | C13—C14 | 1.508 (3) |
| O2—C1 | 1.304 (3) | C13—H13A | 0.97 |
| O2—H2A | 0.82 | C13—H13B | 0.97 |
| O3—C9 | 1.352 (3) | C14—C15 | 1.516 (4) |
| O3—C13 | 1.442 (3) | C14—C16 | 1.526 (4) |
| N1—C3 | 1.310 (3) | C14—H14A | 0.98 |
| N1—C4 | 1.367 (3) | C15—H15A | 0.96 |
| N2—C12 | 1.143 (4) | C15—H15B | 0.96 |
| C1—C2 | 1.485 (3) | C15—H15C | 0.96 |
| C2—C4 | 1.369 (4) | C16—H16A | 0.96 |
| C3—C6 | 1.472 (3) | C16—H16B | 0.96 |
| C4—C5 | 1.494 (3) | C16—H16C | 0.96 |
| C5—H5A | 0.96 | N3—C20 | 1.323 (4) |
| C5—H5B | 0.96 | N3—C19 | 1.330 (4) |
| C5—H5C | 0.96 | C17—C18 | 1.357 (4) |
| C6—C11 | 1.386 (3) | C17—C21 | 1.357 (5) |
| C6—C7 | 1.386 (3) | C17—H17A | 0.93 |
| C7—C8 | 1.391 (3) | C18—C19 | 1.377 (4) |
| C7—H7A | 0.93 | C18—H18A | 0.93 |
| C8—C9 | 1.396 (3) | C19—H19A | 0.93 |
| C8—C12 | 1.432 (4) | C20—C21 | 1.371 (4) |
| C9—C10 | 1.384 (3) | C20—H20A | 0.93 |
| C10—C11 | 1.382 (3) | C21—H21A | 0.93 |
| C2—S—C3 | 89.34 (11) | O3—C13—C14 | 107.94 (19) |
| C1—O2—H2A | 109.5 | O3—C13—H13A | 110.1 |
| C9—O3—C13 | 118.94 (18) | C14—C13—H13A | 110.1 |
| C3—N1—C4 | 111.2 (2) | O3—C13—H13B | 110.1 |
| O1—C1—O2 | 124.6 (2) | C14—C13—H13B | 110.1 |
| O1—C1—C2 | 123.2 (3) | H13A—C13—H13B | 108.4 |
| O2—C1—C2 | 112.2 (2) | C13—C14—C15 | 111.3 (2) |
| C4—C2—C1 | 129.7 (2) | C13—C14—C16 | 109.1 (2) |
| C4—C2—S | 110.16 (17) | C15—C14—C16 | 110.7 (2) |
| C1—C2—S | 120.2 (2) | C13—C14—H14A | 108.6 |
| N1—C3—C6 | 123.1 (2) | C15—C14—H14A | 108.6 |
| N1—C3—S | 114.60 (16) | C16—C14—H14A | 108.6 |
| C6—C3—S | 122.33 (18) | C14—C15—H15A | 109.5 |
| N1—C4—C2 | 114.7 (2) | C14—C15—H15B | 109.5 |
| N1—C4—C5 | 118.6 (2) | H15A—C15—H15B | 109.5 |
| C2—C4—C5 | 126.7 (2) | C14—C15—H15C | 109.5 |
| C4—C5—H5A | 109.5 | H15A—C15—H15C | 109.5 |
| C4—C5—H5B | 109.5 | H15B—C15—H15C | 109.5 |
| H5A—C5—H5B | 109.5 | C14—C16—H16A | 109.5 |
| C4—C5—H5C | 109.5 | C14—C16—H16B | 109.5 |
| H5A—C5—H5C | 109.5 | H16A—C16—H16B | 109.5 |
| H5B—C5—H5C | 109.5 | C14—C16—H16C | 109.5 |
| C11—C6—C7 | 117.9 (2) | H16A—C16—H16C | 109.5 |
| C11—C6—C3 | 121.4 (2) | H16B—C16—H16C | 109.5 |
| C7—C6—C3 | 120.7 (2) | C20—N3—C19 | 117.5 (2) |
| C6—C7—C8 | 120.5 (2) | C18—C17—C21 | 118.6 (3) |
| C6—C7—H7A | 119.8 | C18—C17—H17A | 120.7 |
| C8—C7—H7A | 119.8 | C21—C17—H17A | 120.7 |
| C7—C8—C9 | 120.9 (2) | C17—C18—C19 | 119.4 (3) |
| C7—C8—C12 | 119.5 (2) | C17—C18—H18A | 120.3 |
| C9—C8—C12 | 119.6 (2) | C19—C18—H18A | 120.3 |
| O3—C9—C10 | 125.7 (2) | N3—C19—C18 | 122.2 (3) |
| O3—C9—C8 | 115.8 (2) | N3—C19—H19A | 118.9 |
| C10—C9—C8 | 118.6 (2) | C18—C19—H19A | 118.9 |
| C11—C10—C9 | 119.9 (2) | N3—C20—C21 | 123.0 (3) |
| C11—C10—H10A | 120.0 | N3—C20—H20A | 118.5 |
| C9—C10—H10A | 120.0 | C21—C20—H20A | 118.5 |
| C10—C11—C6 | 122.2 (2) | C17—C21—C20 | 119.2 (3) |
| C10—C11—H11A | 118.9 | C17—C21—H21A | 120.4 |
| C6—C11—H11A | 118.9 | C20—C21—H21A | 120.4 |
| N2—C12—C8 | 178.1 (3) | ||
| O1—C1—C2—C4 | −0.7 (4) | C6—C7—C8—C9 | −0.4 (4) |
| O2—C1—C2—C4 | 179.4 (2) | C6—C7—C8—C12 | −178.2 (2) |
| O1—C1—C2—S | −179.5 (2) | C13—O3—C9—C10 | 0.5 (3) |
| O2—C1—C2—S | 0.6 (3) | C13—O3—C9—C8 | −179.5 (2) |
| C3—S—C2—C4 | 0.17 (19) | C7—C8—C9—O3 | −178.6 (2) |
| C3—S—C2—C1 | 179.2 (2) | C12—C8—C9—O3 | −0.8 (4) |
| C4—N1—C3—C6 | −179.6 (2) | C7—C8—C9—C10 | 1.4 (4) |
| C4—N1—C3—S | 0.1 (3) | C12—C8—C9—C10 | 179.1 (2) |
| C2—S—C3—N1 | −0.1 (2) | O3—C9—C10—C11 | 178.9 (2) |
| C2—S—C3—C6 | 179.5 (2) | C8—C9—C10—C11 | −1.0 (3) |
| C3—N1—C4—C2 | 0.1 (3) | C9—C10—C11—C6 | −0.2 (4) |
| C3—N1—C4—C5 | −179.3 (2) | C7—C6—C11—C10 | 1.1 (4) |
| C1—C2—C4—N1 | −179.0 (2) | C3—C6—C11—C10 | −178.8 (2) |
| S—C2—C4—N1 | −0.2 (3) | C9—O3—C13—C14 | −179.00 (19) |
| C1—C2—C4—C5 | 0.3 (4) | O3—C13—C14—C15 | 64.7 (3) |
| S—C2—C4—C5 | 179.2 (2) | O3—C13—C14—C16 | −173.0 (2) |
| N1—C3—C6—C11 | 2.2 (4) | C21—C17—C18—C19 | −0.1 (5) |
| S—C3—C6—C11 | −177.39 (18) | C20—N3—C19—C18 | 0.0 (4) |
| N1—C3—C6—C7 | −177.7 (2) | C17—C18—C19—N3 | 0.2 (4) |
| S—C3—C6—C7 | 2.7 (3) | C19—N3—C20—C21 | −0.2 (4) |
| C11—C6—C7—C8 | −0.8 (4) | C18—C17—C21—C20 | −0.1 (5) |
| C3—C6—C7—C8 | 179.1 (2) | N3—C20—C21—C17 | 0.2 (5) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2A···N3i | 0.82 | 1.79 | 2.611 (3) | 174 |
| C5—H5A···O1 | 0.96 | 2.52 | 3.055 (3) | 115 |
| Symmetry codes: (i) x, y, z−1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2A···N3i | 0.82 | 1.79 | 2.611 (3) | 174 |
| Symmetry codes: (i) x, y, z−1. |
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The oxidation of xanthine results in the formation of uric acid. Disorders of uric acid metabolism include gout which is the most common inflammatory arthritis initiated by tissue deposition of monosodium urate (MSU) crystals (Alexander, 2008). Some inventions are related to methods of preserving or increasing renal function in a subject by administering a therapeutically effective amount of at least one xanthine oxidoreductase inhibiting compound. 2-(3-Cyano-4-isobutyloxy)phenyl-4-methyl-5-thiazolecarboxylic acid (Febuxostat) is one of the novel drug that have been evaluated and shown to be highly effective in the management of hyperuricemia (Perez-Ruiz et al., 2008; Edwards, 2009), thus enlarging the therapeutic options available to lower uric acid levels. Many patents or papers have been reported on the synthesis, polymorphism and their effect on the stability and bioavailability of this drug (Hiramatsu et al., 2000; Sorbera et al., 2001; Zhou et al., 2007). However, there are few reports on its single-crystal structure. In the present study, we report the crystal structure of the title compound.
The asymmetric unit of the title compound contains one febuxostat molecule and one pyridine molecule. The phenyl ring and thiazole rings of the febuxostat molecule are almost coplanar (Fig. 1), with the dihedral angle between them being 2.4 (1)°. The carboxyl group is coplanar with the thiazole ring as indicated by torsion angles O1—C1—C2—C4 and O2—C1—C2—S of -0.7 (4)° and 0.6 (3)°, respectively. Bond lengths and angles are comparable to those observed in a related structure (Fontrodona et al., 2001).
In the crystal, pyridine moleclue is linked to the febuxostat molecule through a O2—H2A···N3(x, y, 1 + z) hydrogen bond (Table 1). A weak π-π stacking interaction is observed between the benzene ring and pyridine molecule, with a centroid-to-centroid distance of 3.7530 (18) Å.