Acta Cryst. (2007). E63, o3697 [ doi:10.1107/S1600536807037208 ]
In the title compound, C4H3BrO3S2, all bond lengths and angles are within normal ranges. The crystal packing exhibits intermolecular O-H
O hydrogen bonds, which link the molecules into chains extended along the c axis.
5-Bromothiophene-2-sulfonyl chloride (5 mmol, 1.304 g), 2-aminobenzoic acid (5 mmol, 0.685 g) and N,N-dimethylpyridin-4-amine (DMAP) (0.5 mmol, 0.061 g) were added to acetone (15 ml) at room temperature with stirring. The reaction was allowed to proceed for 48 h at room temperature, followed by column chromatographic separation. The purified product was dissoved in ethanol–acetone (1:1), and allowed to stand for approximately 15 d until single crystals formed.
The atom H3 was located on a difference Fourier map, placed in idealized position (O—H 0.82 Å) and refined as riding, with Uiso(H3) = 1.5Ueq(O3). C-bound H atoms were positioned geometrically, and were allowed to ride on their parent atoms at distances of C—H 0.93 Å, with Uiso(H) = 1.2Ueq(C). The highest residual peak [1.28 e Å−3] and deepest hole [−1.21 e Å−3] are situated 0.04 Å at atom S2 and 0.15 Å at atom O3, respectively.
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.
![[Figure 1]](./cv2285fig1thm.gif)
| Fig. 1. A portion of the crystal packing of (I), showing the atom numbering and displacement ellipsoids at the 40% probability level [symmetry code: (A) −x + 3/2, y, z + 1/2]. Dashed line denotes intermolecular hydrogen bond. |
| C4H3BrO3S2 | F000 = 944 |
| Mr = 243.09 | Dx = 2.108 Mg m−3 |
| Orthorhombic, Pccn | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ab 2ac | Cell parameters from 2560 reflections |
| a = 13.7633 (16) Å | θ = 2.8–25.0º |
| b = 14.4540 (17) Å | µ = 5.85 mm−1 |
| c = 7.7020 (9) Å | T = 298 (2) K |
| V = 1532.2 (3) Å3 | Prism, colourless |
| Z = 8 | 0.32 × 0.21 × 0.12 mm |
| Bruker APEX area-detector diffractometer | 1347 independent reflections |
| Radiation source: fine-focus sealed tube | 1191 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.035 |
| T = 298(2) K | θmax = 25.0º |
| φ and ω scans | θmin = 2.0º |
| Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −16→13 |
| Tmin = 0.241, Tmax = 0.500 | k = −17→17 |
| 7333 measured reflections | l = −9→9 |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.050 | w = 1/[σ2(Fo2) + (0.0718P)2 + 4.907P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.134 | (Δ/σ)max < 0.001 |
| S = 1.08 | Δρmax = 1.28 e Å−3 |
| 1347 reflections | Δρmin = −1.21 e Å−3 |
| 93 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0100 (13) |
| Secondary atom site location: difference Fourier map |
| C4H3BrO3S2 | V = 1532.2 (3) Å3 |
| Mr = 243.09 | Z = 8 |
| Orthorhombic, Pccn | Mo Kα |
| a = 13.7633 (16) Å | µ = 5.85 mm−1 |
| b = 14.4540 (17) Å | T = 298 (2) K |
| c = 7.7020 (9) Å | 0.32 × 0.21 × 0.12 mm |
| Bruker APEX area-detector diffractometer | 1347 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2002) | 1191 reflections with I > 2σ(I) |
| Tmin = 0.241, Tmax = 0.500 | Rint = 0.035 |
| 7333 measured reflections |
| R[F2 > 2σ(F2)] = 0.050 | 93 parameters |
| wR(F2) = 0.134 | H-atom parameters constrained |
| S = 1.08 | Δρmax = 1.28 e Å−3 |
| 1347 reflections | Δρmin = −1.21 e Å−3 |
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 > 2sigma(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 | ||
| Br1 | 1.17226 (5) | 0.61516 (5) | 1.03375 (11) | 0.0594 (4) | |
| S1 | 1.06565 (9) | 0.80207 (10) | 0.9827 (2) | 0.0412 (4) | |
| S2 | 0.88696 (9) | 0.91154 (8) | 0.88437 (17) | 0.0346 (4) | |
| O1 | 0.8001 (3) | 0.8886 (3) | 0.7904 (6) | 0.0457 (10) | |
| O2 | 0.9573 (3) | 0.9723 (2) | 0.8092 (5) | 0.0395 (9) | |
| O3 | 0.8528 (3) | 0.9585 (3) | 1.0626 (5) | 0.0459 (10) | |
| H3 | 0.8073 | 0.9291 | 1.1034 | 0.069* | |
| C1 | 1.0605 (4) | 0.6842 (4) | 0.9861 (7) | 0.0366 (12) | |
| C2 | 0.9721 (4) | 0.6498 (4) | 0.9457 (7) | 0.0405 (12) | |
| H2 | 0.9574 | 0.5870 | 0.9417 | 0.049* | |
| C3 | 0.9050 (4) | 0.7209 (4) | 0.9103 (7) | 0.0377 (11) | |
| H3A | 0.8404 | 0.7105 | 0.8809 | 0.045* | |
| C4 | 0.9452 (3) | 0.8064 (3) | 0.9237 (6) | 0.0296 (10) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.0396 (5) | 0.0554 (5) | 0.0834 (6) | 0.0193 (3) | −0.0019 (3) | 0.0086 (3) |
| S1 | 0.0220 (7) | 0.0379 (8) | 0.0637 (9) | −0.0003 (5) | −0.0064 (5) | 0.0044 (6) |
| S2 | 0.0294 (7) | 0.0336 (7) | 0.0408 (7) | −0.0015 (5) | −0.0021 (5) | 0.0069 (5) |
| O1 | 0.0268 (19) | 0.051 (2) | 0.059 (3) | −0.0032 (16) | −0.0157 (18) | 0.0120 (19) |
| O2 | 0.0332 (19) | 0.0395 (19) | 0.046 (2) | −0.0060 (15) | 0.0035 (16) | 0.0103 (16) |
| O3 | 0.038 (2) | 0.048 (2) | 0.052 (2) | 0.0015 (18) | 0.0066 (18) | −0.0026 (19) |
| C1 | 0.034 (3) | 0.035 (3) | 0.040 (3) | 0.009 (2) | 0.001 (2) | 0.001 (2) |
| C2 | 0.042 (3) | 0.032 (3) | 0.048 (3) | 0.001 (2) | −0.001 (2) | −0.002 (2) |
| C3 | 0.029 (3) | 0.037 (3) | 0.047 (3) | −0.004 (2) | −0.005 (2) | −0.001 (2) |
| C4 | 0.021 (2) | 0.033 (3) | 0.035 (3) | −0.0014 (18) | −0.0023 (18) | 0.003 (2) |
| Br1—C1 | 1.870 (5) | O3—H3 | 0.8200 |
| S1—C1 | 1.705 (5) | C1—C2 | 1.351 (8) |
| S1—C4 | 1.720 (5) | C2—C3 | 1.409 (7) |
| S2—O2 | 1.429 (4) | C2—H2 | 0.9300 |
| S2—O1 | 1.437 (4) | C3—C4 | 1.358 (7) |
| S2—O3 | 1.602 (4) | C3—H3A | 0.9300 |
| S2—C4 | 1.745 (5) | ||
| C1—S1—C4 | 90.0 (3) | S1—C1—Br1 | 120.1 (3) |
| O2—S2—O1 | 120.1 (2) | C1—C2—C3 | 111.5 (5) |
| O2—S2—O3 | 106.6 (2) | C1—C2—H2 | 124.3 |
| O1—S2—O3 | 106.6 (2) | C3—C2—H2 | 124.3 |
| O2—S2—C4 | 107.1 (2) | C4—C3—C2 | 112.5 (5) |
| O1—S2—C4 | 105.6 (2) | C4—C3—H3A | 123.8 |
| O3—S2—C4 | 110.8 (2) | C2—C3—H3A | 123.8 |
| S2—O3—H3 | 109.5 | C3—C4—S1 | 112.3 (4) |
| C2—C1—S1 | 113.7 (4) | C3—C4—S2 | 126.3 (4) |
| C2—C1—Br1 | 126.1 (4) | S1—C4—S2 | 121.4 (3) |
| C4—S1—C1—C2 | −0.3 (4) | C1—S1—C4—S2 | −178.4 (3) |
| C4—S1—C1—Br1 | 177.3 (3) | O2—S2—C4—C3 | −144.9 (5) |
| S1—C1—C2—C3 | 0.0 (6) | O1—S2—C4—C3 | −15.8 (5) |
| Br1—C1—C2—C3 | −177.5 (4) | O3—S2—C4—C3 | 99.3 (5) |
| C1—C2—C3—C4 | 0.5 (7) | O2—S2—C4—S1 | 34.0 (4) |
| C2—C3—C4—S1 | −0.8 (6) | O1—S2—C4—S1 | 163.1 (3) |
| C2—C3—C4—S2 | 178.2 (4) | O3—S2—C4—S1 | −81.8 (3) |
| C1—S1—C4—C3 | 0.6 (4) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O1i | 0.82 | 2.14 | 2.920 (5) | 158 |
| Symmetry codes: (i) −x+3/2, y, z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O1i | 0.82 | 2.14 | 2.920 (5) | 158 |
| Symmetry codes: (i) −x+3/2, y, z+1/2. |
The authors acknowledge financial support by Dalian University of Technology and Wenzhou University.
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Bruker (2002). SADABS (Version 2.03), SAINT (Version 6.02), SMART (Version 5.62) and SHELXTL (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA.
Gayathri, D., Velmurugan, D., Ravikumar, K., Poornachandran, M. & Raghunathan, R. (2006). Acta Cryst. E62, o4454–o4455.
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Lin, S.-M., Zheng, M. & Xiong, J. (2007). Acta Cryst. E63, o3177–?.
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Yan, X.-W., Hu, M.-L. & Xiong, J. (2007). Acta Cryst. E63, o678–o679.
Yu, Y.-Y. (2006). Acta Cryst. E62, o2308–o2309.
Some sulfonamide compounds exhibit germicidal activities (Gayathri et al., 2006; Krishnaiah et al., 1995; Yu, 2006), and some crystal structures involving sulfonamide groups have been published (Yan et al., 2007; Lin et al., 2007). 5-Bromothiophene-2-sulfonyl chloride is an important starting material used in synthesis of sulfonamide compounds. Recently, during our synthesis of sulfonamide compounds, the hydrolysate of 5-bromothiophene-2-sulfonyl chloride was obtained unexpectedly. Here we report the crystal structure of the title compound, (I).
In (I) (Fig. 1), all bond lengths and angles show normal values (Allen et al., 1987) and are unremarkable when compared with those found in previous reports (Yan et al., 2007; Lin et al., 2007). The crystal packing exhibits intermolecular O—H···O hydrogen bonds (Table 1), which link the molecules into the chains extended along the c axis.