Acta Cryst. (2008). E64, o1673-o1674 [ doi:10.1107/S1600536808024239 ]
The title molecule, C17H13N5O4S, has a trans configuration with respect to the diazenyl (azo) group. The pyrimidine ring and the terminal benzene ring are inclined at angles of 89.38 (4) and 1.6 (6)°, respectively, with respect to the central benzene ring. The conformation of the molecule is in part stabilized by an intramolecular O-H
O hydrogen bond. In the crystal structure, molecules related through inversion centers form hydrogen-bonded dimers involving the sulfonamide N-H group and the N atom of the pyrimidine ring.
Compound (I) was prepared by the previously reported method in the literature (Mubarak et al., 2007) in which 2.5 g m (0.01 mol) of sulfadiazine was dissolved in 25 ml of distilled water containing 2.5 ml (12M, 2.5 ml, 0.03 mol) of conc. HCl. The resulting solution was then cooled under stirring to 273 K. A cold solution containing 0.69 g m (0.01 mol) of sodium nitrite was drop wisely added to the previous solution to form the diazonium chloride. This solution was then added to a solution containing 1.06 ml of salicylaldehyde (0.01 mol) dissolved in 10 ml of water containing 0.4 g m (0.01 mol) of NaOH. The orange dye, which separated out, was kept in an ice bath under stirring for 30 minutes. The precipitate was then filtered off, washed by distilled water, and finally air_dried (yield: 80%). Analysis calculated for C17H13N5O4S: C, 53.26; H, 3.39; N, 18.27; S, 8.35% found: C, 53.44; H, 3.34; N, 18.38; S, 8.25%. IR (ν, cm-1): 3424(w), 3358(w), 3082(w), 3041(w), 2944(w), 2814(w), 2727(w), 1652(s), 1621(m), 1581(s), 1496(s), 1443(s), 1410(s), 1384(m), 1339(s), 1305(m), 1289(s), 1269(m), 1206(m), 1166(s), 1154(s), 1141(w), 1001(m), 952(s), 902(m), 840(s), 797(s), 772(w), 750(s), 729(s), 669(s), 640(s), 606(s), 582(s), 564(s), 540(w), 531(w), 521(m), 509(m), 455(s), 432(m), 424(w), 403(m). A good crystal suitable for x-ray measurement was prepared by vapour diffusion method in which compound (I) was dissolved in the least possible amount of DMF and then the solution was left at room temperature in the presence of water pool outside. The outside water slowly diffused by vapour and gradually mixed with DMF of the dye. After 7 days, dark orange crystals suitable for X-ray diffraction analysis was separated out.
All H atoms were placed in idealized positions, (C—H = 0.95 Å, O—H = 0.84 Å, and N—H = 0.88 Å), and included in the refinement in a riding-model approximation, with Uiso(H) = 1.2Ueq (C and N) and Uiso(H) = 1.5Ueq (O). In the final difference Fourier map, the highest peak was located 0.83 Å from atom C10. The deepest hole was located 0.64 Å from atom S1.
Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: KENX (Sakai, 2004); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), TEXSAN (Molecular Structure Corporation, 2001), KENX (Sakai, 2004) and ORTEPII (Johnson, 1976).
![[Figure 1]](./lh2668fig1thm.gif)
| Fig. 1. The molecular structure of (I) showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. |
![[Figure 2]](./lh2668fig2thm.gif)
| Fig. 2. Part of the crystal structure showing a pair of molecules [symmetry code: (i)1 - x, 2 - y, 1 - z] stabilized by intra- and intermolecular hydrogen bonds (dashed lines). |
| C17H13N5O4S | F000 = 792 |
| Mr = 383.39 | ? # Insert any comments here. |
| Monoclinic, P21/c | Dx = 1.521 Mg m−3 |
| Hall symbol: -P 2ybc | Mo Kα radiation λ = 0.71073 Å |
| a = 18.579 (2) Å | Cell parameters from 9950 reflections |
| b = 5.7731 (7) Å | θ = 2.4–28.3º |
| c = 17.372 (2) Å | µ = 0.23 mm−1 |
| β = 115.99 (1)º | T = 100 (2) K |
| V = 1674.73 Å3 | Block, dark orange |
| Z = 4 | 0.30 × 0.20 × 0.10 mm |
| Bruker SMART APEX CCD diffractometer | 3560 independent reflections |
| Radiation source: fine-focus sealed tube | 3277 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.017 |
| T = 100(2) K | θmax = 26.7º |
| φ and ω scans | θmin = 2.4º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −23→23 |
| Tmin = 0.934, Tmax = 0.977 | k = −7→7 |
| 17304 measured reflections | l = −21→21 |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo2) + (0.0513P)2 + 0.9337P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.097 | (Δ/σ)max = 0.001 |
| S = 1.05 | Δρmax = 0.42 e Å−3 |
| 3560 reflections | Δρmin = −0.37 e Å−3 |
| 245 parameters | Extinction correction: none |
| Secondary atom site location: difference Fourier map |
| C17H13N5O4S | V = 1674.73 Å3 |
| Mr = 383.39 | Z = 4 |
| Monoclinic, P21/c | Mo Kα |
| a = 18.579 (2) Å | µ = 0.23 mm−1 |
| b = 5.7731 (7) Å | T = 100 (2) K |
| c = 17.372 (2) Å | 0.30 × 0.20 × 0.10 mm |
| β = 115.99 (1)º |
| Bruker SMART APEX CCD diffractometer | 3560 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3277 reflections with I > 2σ(I) |
| Tmin = 0.934, Tmax = 0.977 | Rint = 0.017 |
| 17304 measured reflections |
| R[F2 > 2σ(F2)] = 0.034 | 245 parameters |
| wR(F2) = 0.097 | H-atom parameters constrained |
| S = 1.05 | Δρmax = 0.42 e Å−3 |
| 3560 reflections | Δρmin = −0.37 e Å−3 |
Experimental. The first 50 frames were rescanned at the end of data collection to evaluate any possible decay phenomenon. Since it was judged to be negligible, no decay correction was applied to the data. |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 13.7836 (0.0041) x + 2.4391 (0.0022) y - 13.7785 (0.0036) z = 4.2437 (0.0052) * 0.0258 (0.0010) O1 * -0.0309 (0.0010) O2 * 0.0133 (0.0012) C1 * -0.0188 (0.0013) C2 * -0.0067 (0.0012) C3 * 0.0010 (0.0012) C4 * 0.0430 (0.0013) C5 * 0.0139 (0.0012) C6 * -0.0207 (0.0013) C7 * -0.0198 (0.0009) N1 - 0.1255 (0.0017) N2 - 0.2396 (0.0024) C9 - 0.2576 (0.0024) C10 - 0.2407 (0.0024) C11 - 0.2117 (0.0022) C12 - 0.1607 (0.0019) C13 Rms deviation of fitted atoms = 0.0225 13.5655 (0.0045) x + 2.3850 (0.0032) y - 14.0573 (0.0043) z = 3.6030 (0.0035) Angle to previous plane (with approximate e.s.d.) = 1.60 (0.06) * 0.0132 (0.0011) N2 * -0.0021 (0.0008) C9 * -0.0021 (0.0012) C10 * -0.0053 (0.0012) C11 * -0.0149 (0.0012) C12 * 0.0178 (0.0013) C13 * -0.0066 (0.0004) O1 - 0.0637 (0.0021) O2 0.0152 (0.0018) C1 0.0043 (0.0016) C2 0.0555 (0.0016) C3 0.0836 (0.0016) C4 0.1066 (0.0021) C5 0.0390 (0.0023) C6 - 0.0162 (0.0020) C7 0.1025 (0.0013) N1 Rms deviation of fitted atoms = 0.0106 2.8895 (0.0099) x + 3.8287 (0.0026) y + 10.2469 (0.0065) z = 10.3651 (0.0036) Angle to previous plane (with approximate e.s.d.) = 89.38 (0.04) * -0.0192 (0.0009) N3 * 0.0179 (0.0011) N4 * 0.0136 (0.0010) N5 * 0.0038 (0.0012) C14 * -0.0009 (0.0012) C15 * -0.0197 (0.0013) C16 * 0.0045 (0.0011) C17 Rms deviation of fitted atoms = 0.0136 |
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 | ||
| S1 | 0.67904 (2) | 0.77281 (6) | 0.52372 (2) | 0.02455 (11) | |
| O1 | 1.32533 (7) | 0.9734 (2) | 1.18827 (7) | 0.0366 (3) | |
| N5 | 0.49729 (7) | 0.7981 (2) | 0.57442 (7) | 0.0246 (3) | |
| O4 | 0.67616 (6) | 0.9243 (2) | 0.45700 (6) | 0.0301 (2) | |
| O3 | 0.68746 (6) | 0.52911 (19) | 0.51537 (7) | 0.0297 (2) | |
| C17 | 0.46694 (9) | 0.6915 (3) | 0.62192 (9) | 0.0289 (3) | |
| H13 | 0.4169 | 0.7418 | 0.6183 | 0.035* | |
| N2 | 0.94619 (7) | 1.1123 (2) | 0.84456 (8) | 0.0282 (3) | |
| N3 | 0.59631 (7) | 0.8311 (2) | 0.53095 (8) | 0.0280 (3) | |
| H10 | 0.5668 | 0.9446 | 0.4987 | 0.034* | |
| N1 | 1.00856 (7) | 0.9914 (2) | 0.87789 (8) | 0.0280 (3) | |
| O2 | 1.24471 (7) | 1.3545 (2) | 1.17919 (7) | 0.0332 (3) | |
| H1 | 1.2835 | 1.2624 | 1.2013 | 0.050* | |
| C15 | 0.57921 (10) | 0.4485 (3) | 0.68056 (10) | 0.0357 (4) | |
| H11 | 0.6079 | 0.3262 | 0.7181 | 0.043* | |
| C16 | 0.50602 (9) | 0.5108 (3) | 0.67607 (10) | 0.0338 (3) | |
| H12 | 0.4835 | 0.4332 | 0.7086 | 0.041* | |
| C1 | 1.26947 (9) | 0.9081 (3) | 1.12173 (10) | 0.0310 (3) | |
| H2 | 1.2736 | 0.7616 | 1.0991 | 0.037* | |
| C5 | 1.06241 (9) | 1.3131 (3) | 0.98413 (10) | 0.0297 (3) | |
| H4 | 1.0171 | 1.4067 | 0.9518 | 0.036* | |
| C6 | 1.12111 (9) | 1.3967 (3) | 1.05977 (10) | 0.0299 (3) | |
| H5 | 1.1155 | 1.5451 | 1.0802 | 0.036* | |
| C12 | 0.81694 (9) | 1.1545 (3) | 0.72898 (9) | 0.0288 (3) | |
| H9 | 0.8145 | 1.2998 | 0.7534 | 0.035* | |
| C11 | 0.75308 (9) | 1.0818 (3) | 0.65434 (9) | 0.0286 (3) | |
| H8 | 0.7074 | 1.1777 | 0.6262 | 0.034* | |
| C8 | 0.88818 (9) | 0.7981 (3) | 0.73479 (9) | 0.0279 (3) | |
| H6 | 0.9343 | 0.7034 | 0.7621 | 0.034* | |
| C7 | 1.18899 (9) | 1.2628 (3) | 1.10648 (9) | 0.0269 (3) | |
| C4 | 1.06845 (9) | 1.0915 (3) | 0.95400 (9) | 0.0265 (3) | |
| C3 | 1.13632 (9) | 0.9607 (3) | 0.99930 (9) | 0.0266 (3) | |
| H3 | 1.1417 | 0.8129 | 0.9783 | 0.032* | |
| C9 | 0.82375 (9) | 0.7222 (3) | 0.66129 (9) | 0.0264 (3) | |
| H7 | 0.8249 | 0.5737 | 0.6383 | 0.032* | |
| C13 | 0.88463 (9) | 1.0158 (3) | 0.76846 (9) | 0.0266 (3) | |
| C2 | 1.19719 (9) | 1.0441 (3) | 1.07584 (9) | 0.0266 (3) | |
| N4 | 0.61192 (8) | 0.5519 (2) | 0.63453 (8) | 0.0328 (3) | |
| C14 | 0.56803 (8) | 0.7196 (2) | 0.58287 (9) | 0.0246 (3) | |
| C10 | 0.75726 (8) | 0.8652 (3) | 0.62140 (9) | 0.0242 (3) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.02184 (18) | 0.0280 (2) | 0.02274 (19) | 0.00350 (13) | 0.00873 (14) | 0.00169 (13) |
| O1 | 0.0312 (6) | 0.0394 (6) | 0.0338 (6) | 0.0059 (5) | 0.0091 (5) | 0.0096 (5) |
| N5 | 0.0208 (6) | 0.0265 (6) | 0.0224 (6) | 0.0000 (5) | 0.0057 (5) | 0.0021 (5) |
| O4 | 0.0290 (5) | 0.0365 (6) | 0.0256 (5) | 0.0041 (4) | 0.0127 (4) | 0.0044 (4) |
| O3 | 0.0266 (5) | 0.0294 (6) | 0.0289 (5) | 0.0017 (4) | 0.0083 (4) | −0.0033 (4) |
| C17 | 0.0238 (7) | 0.0335 (8) | 0.0269 (7) | −0.0013 (6) | 0.0090 (6) | 0.0028 (6) |
| N2 | 0.0279 (6) | 0.0288 (6) | 0.0271 (6) | 0.0006 (5) | 0.0114 (5) | −0.0006 (5) |
| N3 | 0.0231 (6) | 0.0318 (7) | 0.0284 (6) | 0.0076 (5) | 0.0107 (5) | 0.0102 (5) |
| N1 | 0.0277 (6) | 0.0293 (6) | 0.0275 (6) | 0.0005 (5) | 0.0127 (5) | 0.0003 (5) |
| O2 | 0.0292 (6) | 0.0361 (6) | 0.0280 (5) | 0.0013 (5) | 0.0066 (4) | −0.0008 (5) |
| C15 | 0.0342 (8) | 0.0351 (8) | 0.0319 (8) | 0.0044 (7) | 0.0091 (6) | 0.0127 (7) |
| C16 | 0.0312 (8) | 0.0368 (8) | 0.0310 (7) | −0.0031 (6) | 0.0115 (6) | 0.0091 (6) |
| C1 | 0.0311 (7) | 0.0297 (8) | 0.0333 (8) | 0.0039 (6) | 0.0150 (6) | 0.0073 (6) |
| C5 | 0.0255 (7) | 0.0300 (8) | 0.0311 (8) | 0.0052 (6) | 0.0100 (6) | 0.0016 (6) |
| C6 | 0.0301 (7) | 0.0261 (7) | 0.0323 (8) | 0.0024 (6) | 0.0127 (6) | −0.0017 (6) |
| C12 | 0.0341 (8) | 0.0228 (7) | 0.0294 (7) | 0.0023 (6) | 0.0139 (6) | −0.0011 (6) |
| C11 | 0.0295 (7) | 0.0258 (7) | 0.0289 (7) | 0.0065 (6) | 0.0114 (6) | 0.0034 (6) |
| C8 | 0.0245 (7) | 0.0319 (8) | 0.0267 (7) | 0.0056 (6) | 0.0105 (6) | 0.0004 (6) |
| C7 | 0.0256 (7) | 0.0298 (7) | 0.0257 (7) | −0.0016 (6) | 0.0116 (6) | 0.0022 (6) |
| C4 | 0.0264 (7) | 0.0287 (7) | 0.0256 (7) | −0.0005 (6) | 0.0126 (6) | 0.0003 (6) |
| C3 | 0.0297 (7) | 0.0240 (7) | 0.0296 (7) | 0.0006 (6) | 0.0162 (6) | 0.0016 (6) |
| C9 | 0.0272 (7) | 0.0264 (7) | 0.0266 (7) | 0.0044 (6) | 0.0129 (6) | −0.0010 (6) |
| C13 | 0.0272 (7) | 0.0289 (7) | 0.0243 (7) | −0.0008 (6) | 0.0118 (6) | 0.0002 (6) |
| C2 | 0.0265 (7) | 0.0272 (7) | 0.0280 (7) | 0.0011 (6) | 0.0138 (6) | 0.0057 (6) |
| N4 | 0.0275 (6) | 0.0359 (7) | 0.0309 (7) | 0.0074 (5) | 0.0091 (5) | 0.0113 (6) |
| C14 | 0.0220 (6) | 0.0261 (7) | 0.0220 (6) | 0.0002 (5) | 0.0064 (5) | 0.0011 (5) |
| C10 | 0.0236 (7) | 0.0276 (7) | 0.0214 (6) | 0.0013 (5) | 0.0099 (5) | 0.0012 (5) |
| S1—O3 | 1.4299 (11) | C11—C10 | 1.391 (2) |
| S1—O4 | 1.4343 (11) | C8—C9 | 1.384 (2) |
| S1—N3 | 1.6311 (12) | C8—C13 | 1.400 (2) |
| S1—C10 | 1.7647 (15) | C7—C2 | 1.404 (2) |
| O1—C1 | 1.226 (2) | C4—C3 | 1.382 (2) |
| N5—C14 | 1.3362 (19) | C3—C2 | 1.400 (2) |
| N5—C17 | 1.3362 (19) | C9—C10 | 1.392 (2) |
| C17—C16 | 1.379 (2) | C1—O3i | 2.9106 (19) |
| N2—N1 | 1.2558 (18) | C5—H4 | 0.9500 |
| N2—C13 | 1.4285 (19) | N3—H10 | 0.8800 |
| N3—C14 | 1.3857 (19) | C1—H2 | 0.9500 |
| N4—C14 | 1.3289 (19) | C6—H5 | 0.9500 |
| N1—C4 | 1.4250 (19) | C8—H6 | 0.9500 |
| O2—C7 | 1.3420 (18) | C15—H11 | 0.9500 |
| C15—N4 | 1.338 (2) | C16—H12 | 0.9500 |
| C15—C16 | 1.375 (2) | C12—H9 | 0.9500 |
| C1—C2 | 1.455 (2) | O2—H1 | 0.8400 |
| C5—C6 | 1.376 (2) | C11—H8 | 0.9500 |
| C5—C4 | 1.405 (2) | C3—H3 | 0.9500 |
| C6—C7 | 1.396 (2) | C17—H13 | 0.9500 |
| C12—C11 | 1.384 (2) | C9—H7 | 0.9500 |
| C12—C13 | 1.392 (2) | ||
| O3—S1—O4 | 119.02 (7) | C13—C12—H9 | 119.8 |
| O3—S1—N3 | 111.08 (7) | C12—C11—C10 | 118.57 (13) |
| O4—S1—N3 | 103.51 (6) | C12—C11—H8 | 120.7 |
| O3—S1—C10 | 108.31 (7) | C10—C11—H8 | 120.7 |
| O4—S1—C10 | 108.42 (7) | C9—C8—C13 | 119.32 (13) |
| N3—S1—C10 | 105.68 (7) | C9—C8—H6 | 120.3 |
| C14—N5—C17 | 115.89 (13) | C13—C8—H6 | 120.3 |
| N5—C17—C16 | 122.09 (14) | O2—C7—C6 | 117.16 (14) |
| N5—C17—H13 | 119.0 | O2—C7—C2 | 122.97 (13) |
| C16—C17—H13 | 119.0 | C6—C7—C2 | 119.87 (14) |
| N1—N2—C13 | 114.37 (13) | C3—C4—C5 | 119.16 (14) |
| C14—N3—S1 | 126.38 (10) | C3—C4—N1 | 116.95 (13) |
| C14—N3—H10 | 116.8 | C5—C4—N1 | 123.89 (13) |
| S1—N3—H10 | 116.8 | C4—C3—C2 | 120.56 (14) |
| N2—N1—C4 | 112.94 (13) | C4—C3—H3 | 119.7 |
| C7—O2—H1 | 109.5 | C2—C3—H3 | 119.7 |
| N4—C15—C16 | 123.09 (15) | C8—C9—C10 | 119.44 (14) |
| N4—C15—H11 | 118.5 | C8—C9—H7 | 120.3 |
| C16—C15—H11 | 118.5 | C10—C9—H7 | 120.3 |
| C15—C16—C17 | 116.64 (14) | C12—C13—C8 | 120.55 (14) |
| C15—C16—H12 | 121.7 | C12—C13—N2 | 114.57 (13) |
| C17—C16—H12 | 121.7 | C8—C13—N2 | 124.86 (13) |
| O1—C1—C2 | 123.15 (15) | C3—C2—C7 | 119.50 (13) |
| O1—C1—H2 | 118.4 | C3—C2—C1 | 120.14 (14) |
| C2—C1—H2 | 118.4 | C7—C2—C1 | 120.34 (14) |
| C6—C5—C4 | 121.07 (14) | C14—N4—C15 | 115.06 (13) |
| C6—C5—H4 | 119.5 | N4—C14—N5 | 127.19 (14) |
| C4—C5—H4 | 119.5 | N4—C14—N3 | 118.86 (13) |
| C5—C6—C7 | 119.78 (14) | N5—C14—N3 | 113.95 (12) |
| C5—C6—H5 | 120.1 | C11—C10—C9 | 121.71 (13) |
| C7—C6—H5 | 120.1 | C11—C10—S1 | 119.74 (11) |
| C11—C12—C13 | 120.37 (14) | C9—C10—S1 | 118.47 (11) |
| C11—C12—H9 | 119.8 | ||
| C14—N5—C17—C16 | −0.3 (2) | C4—C3—C2—C1 | −178.17 (13) |
| O3—S1—N3—C14 | 46.71 (15) | O2—C7—C2—C3 | −179.94 (13) |
| O4—S1—N3—C14 | 175.57 (13) | C6—C7—C2—C3 | −1.2 (2) |
| C10—S1—N3—C14 | −70.55 (14) | O2—C7—C2—C1 | −1.9 (2) |
| C13—N2—N1—C4 | −179.50 (12) | C6—C7—C2—C1 | 176.90 (14) |
| N4—C15—C16—C17 | −1.1 (3) | O1—C1—C2—C3 | 178.82 (14) |
| N5—C17—C16—C15 | 1.6 (2) | O1—C1—C2—C7 | 0.8 (2) |
| C4—C5—C6—C7 | 1.8 (2) | C16—C15—N4—C14 | −0.6 (2) |
| C13—C12—C11—C10 | 1.9 (2) | C15—N4—C14—N5 | 2.2 (2) |
| C5—C6—C7—O2 | 179.17 (13) | C15—N4—C14—N3 | −178.08 (14) |
| C5—C6—C7—C2 | 0.3 (2) | C17—N5—C14—N4 | −1.7 (2) |
| C6—C5—C4—C3 | −3.0 (2) | C17—N5—C14—N3 | 178.51 (13) |
| C6—C5—C4—N1 | 177.69 (14) | S1—N3—C14—N4 | 2.0 (2) |
| N2—N1—C4—C3 | 174.33 (13) | S1—N3—C14—N5 | −178.19 (11) |
| N2—N1—C4—C5 | −6.4 (2) | C12—C11—C10—C9 | −0.3 (2) |
| C5—C4—C3—C2 | 2.2 (2) | C12—C11—C10—S1 | −177.03 (11) |
| N1—C4—C3—C2 | −178.51 (12) | C8—C9—C10—C11 | −1.2 (2) |
| C13—C8—C9—C10 | 1.1 (2) | C8—C9—C10—S1 | 175.57 (11) |
| C11—C12—C13—C8 | −2.0 (2) | O3—S1—C10—C11 | −165.58 (11) |
| C11—C12—C13—N2 | 179.57 (13) | O4—S1—C10—C11 | 63.96 (13) |
| C9—C8—C13—C12 | 0.4 (2) | N3—S1—C10—C11 | −46.48 (13) |
| C9—C8—C13—N2 | 178.74 (14) | O3—S1—C10—C9 | 17.59 (14) |
| N1—N2—C13—C12 | −177.01 (13) | O4—S1—C10—C9 | −112.87 (12) |
| N1—N2—C13—C8 | 4.6 (2) | N3—S1—C10—C9 | 136.69 (12) |
| C4—C3—C2—C7 | −0.1 (2) |
| Symmetry codes: i. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H1···O1 | 0.84 | 1.90 | 2.6269 (17) | 145 |
| N3—H10···N5i | 0.88 | 1.98 | 2.8574 (17) | 179 |
| Symmetry codes: (i) −x+1, −y+2, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H1···O1 | 0.84 | 1.90 | 2.6269 (17) | 145 |
| N3—H10···N5i | 0.88 | 1.98 | 2.8574 (17) | 179 |
| Symmetry codes: (i) −x+1, −y+2, −z+1. |
This work was supported by a Grant-in-Aid for Specially Promoted Research (No. 18002016) from the Ministry of Education, Culture, Sports, Science, and Technology of Japan. HE acknowledges the Egyptian Channel System for financial support to promote the joint research project between Tanta and Kyushu Universities.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Open, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19.
Bruker (2004). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Gaber, M., El-Baradie, K. & El-Sayed, Y. (2008). Spectrochim. Acta (A), 69, 543–541.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Kakoti, M., Choudhury, S., Deb, A. K. & Goswami, S. (1993). Polyhedron, 12, 783–789.
La Roche, H. & Co, A. G. (1967a). Chem. Abstr. 67, 733 23r.
La Roche, H. & Co, A. G. (1967b). Swiss Patent, Neth. Apt. 66610, 566 (Cl. CO 7d). 31.
Misra, T. K., Das, D., Sinha, C., Ghosh, P. & Pal, C. K. (1998). Inorg. Chem. 37, 8, 1672–1678.
Molecular Structure Corporation (2001). TEXSAN. MSC,The Woodlands, Texas, USA.
Mubarak, A. T., El-Sonbati, A. Z. & Ahmed, S. M. (2007). J. Coord. Chem. 60, 17, 1877–1890.
Nagaraja, P., Sunith, K., Vasantha, R. & Yathirajan, H. (2002). Eur. J. Pharm. Biopharm. 53, 187–192.
Sakai, K. (2004). KENX. Kyushu University, Japan.
Santra, B. K. & Lahiri, G. K. (1997). J. Chem. Soc. Dalton Trans. pp. 1883–1888.
Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Vaichulis, A. J. (1977). US Patent 8 273 352 .
Sulfa-drugs are widely used in the treatment of infections, especially for patients intolerant to antibiotics (Nagaraja et al., 2002). The vast commercial success of these medical agents has made the chemistry of sulfonamides become a major area of research and an important branch of commercial importance in pharmaceutical sciences (Nagaraja et al., 2002). Heterocyclic azo compounds are also considered very important class of compounds. The importance of these compounds may stem from its biological activity and analytical investigations (Gaber et al., 2008). Also, it is well known that heterocyclic azo compounds have been used to establish the low oxidation states of different metal ions (Kakoti et al., 1993; Santra & Lahiri, 1997; Misra et al., 1998). What appears more important is that sulfonamide and azo-sulfonamide derivatives have been found to be biologically versatile anticancer (La Roche & Co, 1967a,b) and antitubercular (Vaichulis, 1977) drugs.
In the title compound (I), C17H13N5O4S, the two aromatic groups attached to the azo double bond are oriented in a trans fashion. All the bond lengths are found to be within the normal values (Allen et al., 1987). An intramolecular hydrogen bond is formed between the O—H (hydroxyl) group and the oxygen atom of the carbonyl group (O2—H1···O1; Table 1), stabilizing the coformation of the molecule. Moreover, the molecule is further correlated with an adjacent molecule through an inversion center, where the intermolecular interaction is stabilized with two hydrogen bonds formed between the N—H(sulfonamide) group and the nitrogen atom of pyrimidine ring, N3—H···N5i hydrogen bond [symmetry code: (i) 1 - x, 2 - y, 1 - z] (see Fig. 2 and Table 1). There is an unusually short intermolecular contact between the C (carbonyl) and the O (sulfonamide) atoms, i.e., C1···O3ii = 2.91 (2) Å [symmetry code: (ii) 2 - x, 1/2 + y, 3/2 - z]. Although the rotation about the C10—S1 bond axis is essentially allowed, the rotation at this geometry is fixed as a result of strong intermolecular hydrogen bonds formed at the peripheral pyrimidine attached to the sulfonamide unit. This must be the major cause of the short contact found for one of the sulfonamide oxygen atoms, i.e., O3.
The pyrimidine ring and both the central and terminal benzene rings are found to have a planar geometry (r.m.s deviations are 0.0136, 0.0106 and 0.0225 Å, respectively). Both the pyrimidine and the terminal phenyl rings are canted with respect to the central phenyl ring at angle of 89.38 (4) and 1.6 (6)°, respectively.