Jian-hong Wu, Yin‐Qiu Liu, Ling Huang
2009
Citations
0
Influential Citations
0
Citations
Journal
Zeitschrift für Kristallographie - New Crystal Structures
Abstract
C9H12O7.5S, monoclinic, C12/c1 (no. 15), a = 10.6986(8) Å, b = 11.4439(8) Å, c = 20.975(2) Å, * = 104.529(2)°, V = 2485.9 Å, Z = 8, Rgt(F) = 0.063, wRref(F) = 0.150, T = 293 K. Source of material 3-(Ethoxycarbonyl)-4-hydroxybenzenesulfonic acid of analytical grade was obtained commercially. Crystals of the title compound were acquired after 0.246 g (0.001 mol) 3-(ethoxycarbonyl)-4-hydroxybenzenesulfonic acid was recrystallized from 30 ml ethanol by means of solvent escaping in the air. Experimental details All H atoms except that of water were located at calculated positions and refined as riding on their parent atoms with the bond length fixed to 0.93 Å (phen), 0.97 Å (methylene), 0.96 Å (methyl) and 0.82 Å (hydroxyl) and with Uiso(H) = 1.2 Ueq(C,O) with the exception of Uiso(H) = 1.5 Ueq(C) for methyl group. The H atoms of water molecules were found in difference Fourier map and refined with d(O—H) fixed to 0.82 Å and Uiso(H) = 1.2 Ueq(O). Discussion The asymmetric unit of the title crystal structure consists of one 3(ethoxycarbonyl)-4-hydroxybenzenesulfonic acid molecule and one and half discrete water molecules (figure, top). All nonhydrogen atoms of the ethoxycarbonyl group are approximately coplanar with the benzene ring, the maximum deviation from the least-squares plane through all relevant atoms being 0.165 Å for C9. Terminal sulfonic group shows disorder in orientations due to the rotation of bond C—S, resulting in low Ueq as compared to neighbours O atoms for S1. The O atoms of the sulfonic group act as donors of hydrogen bonds with neighbouring water molecules, which connect adjacent discrete molecules into the crystal’s 3D network (figure, bottom). Many similar structures have been reported, of which the most related were two derivatives: ethyl 5nitrosalicylate [1] and ethyl 5-bromosalicylate[2], in which the sulfonic group are substituted by NO2 group and by Br, respectively. In the two compounds all nonhydrogen atoms of the ethoxycarbonyl group are approximately coplanar with its benzene ring, which are similar to the situations appearing in the title compound. Z. Kristallogr. NCS 224 (2009) 689-690 / DOI 10.1524/ncrs.2009.0303 689 © by Oldenbourg Wissenschaftsverlag, München Crystal: colorless block, size 0.290 × 0.300 × 0.330 mm Wavelength: Mo Kα radiation (0.71073 Å) .: 2.85 cm−1 Diffractometer, scan mode: Bruker SMART CCD, #/% 2,max: 51° N(hkl)measured, N(hkl)unique: 7578, 2293 Criterion for Iobs, N(hkl)gt: Iobs > 2 )(Iobs), 1773 N(param)refined: 170 Programs: SHELXS-97 [1], SHELXL-97 [2], SHELXTL [3], DIAMOND [4] Table 1. Data collection and handling. H(2) 8f 0.4327 0.6342 0.1505 0.077 H(3) 8f 0.4668 0.5634 0.0538 0.082 H(6) 8f 0.0579 0.6813 0.0641 0.063 H(8A) 8f −0.1335 0.7027 −0.1463 0.102 H(8B) 8f −0.1902 0.5851 −0.1266 0.102 H(9A) 8f −0.3014 0.6849 −0.0645 0.177 H(9B) 8f −0.3369 0.7375 −0.1357 0.177 H(9C) 8f −0.2392 0.8029 −0.0787 0.177 H(6A) 8f 0.927(2) 0.506(5) 0.245(3) 0.141 H(7A) 8f 0.368(4) 0.515(5) 0.258(3) 0.141 H(7B) 8f 0.410(6) 0.408(2) 0.292(3) 0.141 H(4) 8f 0.2438 0.5392 −0.0857 0.103 Table 2. Atomic coordinates and displacement parameters (in Å). Atom Site x y z Uiso