Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029261/dn2196sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029261/dn2196Isup2.hkl |
CCDC reference: 654797
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.015 Å
- R factor = 0.070
- wR factor = 0.151
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT213_ALERT_2_C Atom F1 has ADP max/min Ratio ............. 3.40 prola PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.70 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.10 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 15 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.11 Ratio
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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
The title compound was prepared according to the literature method (Gowda & Usha, 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Gowda & Usha, 2003). Single crystals of the title compound were obtained from its aqueous solution and used for X-ray diffraction studies at room temperature.
H atoms of the benzene ring were positioned geometrically and refined using a riding model with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(C). H atoms of the water molecules (O3w, O4w) were visible in difference map and were subsequently treated as riding with mutual distance restrained to 1.35 (5) Å and O—H bond length 0.82 (5) Å. No restraints were applied to non-hydrogen atoms.
The chemistry of N-bromo-arylsulfonamides is of interest due to their distinct physical, chemical and biological properties (Usha & Gowda, 2006). In the present work, the structure of sodium N-bromo-4-fluoro- benzenesulfonamidate (NaNB4FBSA) has been determined to study the substituent effects on the solid state structures of arylsulfonamides and N-halo arylsulfonamidates (Gowda, Jyothi et al., 2007; Gowda et al., 2007a,b; Gowda, Usha et al., 2007). The structure of NaNB4FBSA (Fig. 1) is similar to those of sodium N-bromo-benzenesulfonamidate(NaNBBSA)(Gowda, Usha et al., 2007) and sodium N-bromo-4-chloro-benzenesulfonamidate (NaNB4CBSA)(Gowda, Kožíšek et al., 2007a) and sodium N-chloro-arylsulfonamidates (George et al., 2000; Gowda, Jyothi et al., 2007). NaNB4FBSA crystallizes with two cations, two anions and three water molecules in the asymmetric unit. The sodium ion shows octahedral coordination by three O atoms of three different water molecules and by three sulfonyl O atoms of three different N-bromo-4-fluoro-benzenesulfonamide anions. There is no interaction between the nitrogen and sodium ions in the molecule. The S—N distances of N1—S1, 1.591 (6) Å is consistent with a S—N double bond and in agreement with those observed with NaNBBSA, NaNB4CBSA and sodium N-chloro- arylsulfonamidates. The occurrence of O—H···N hydrogen bonds between the wat er molecules and N atom associated with the presence of Na+ result in the formation of thick layered structure parallel to the (0 0 1) plane (Table 1, Fig. 1). This thick layer may be described as build up from an internal layer containing Na atoms and water molecules sandwiched by the benzenesulfonamidate with the fluorobenzene pointing outward.
For related literature, see: George et al. (2000); Gowda & Usha (2003); Gowda, Jyothi et al. (2007); Gowda, Kožíšek et al. (2007a,b); Gowda, Usha et al. (2007); Usha & Gowda (2006).
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: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003) and WinGX (Farrugia, 1999).
Na+·C6H4BrFNO2S−·1.5H2O | Z = 8 |
Mr = 303.09 | F(000) = 1192 |
Monoclinic, C2/c | Dx = 1.946 Mg m−3 |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.3985 (8) Å | µ = 4.22 mm−1 |
b = 6.7027 (4) Å | T = 299 K |
c = 29.892 (2) Å | Plate, yellow |
β = 96.710 (8)° | 0.44 × 0.34 × 0.15 mm |
V = 2069.1 (2) Å3 |
Oxford Diffraction Xcalibur diffractometer | 2009 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1798 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 8.4012 pixels mm-1 | θmax = 26.0°, θmin = 5.2° |
Rotation method data acquisition using ω and φ scans | h = −12→12 |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006) using a multifaceted crystal model (Clark & Reid, 1995) | k = −8→7 |
Tmin = 0.187, Tmax = 0.561 | l = −36→36 |
6114 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.070 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.021P)2 + 67.2P] where P = (Fo2 + 2Fc2)/3 |
2009 reflections | (Δ/σ)max = 0.001 |
141 parameters | Δρmax = 0.60 e Å−3 |
4 restraints | Δρmin = −0.94 e Å−3 |
Na+·C6H4BrFNO2S−·1.5H2O | V = 2069.1 (2) Å3 |
Mr = 303.09 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 10.3985 (8) Å | µ = 4.22 mm−1 |
b = 6.7027 (4) Å | T = 299 K |
c = 29.892 (2) Å | 0.44 × 0.34 × 0.15 mm |
β = 96.710 (8)° |
Oxford Diffraction Xcalibur diffractometer | 2009 independent reflections |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006) using a multifaceted crystal model (Clark & Reid, 1995) | 1798 reflections with I > 2σ(I) |
Tmin = 0.187, Tmax = 0.561 | Rint = 0.025 |
6114 measured reflections |
R[F2 > 2σ(F2)] = 0.070 | 4 restraints |
wR(F2) = 0.151 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.021P)2 + 67.2P] where P = (Fo2 + 2Fc2)/3 |
2009 reflections | Δρmax = 0.60 e Å−3 |
141 parameters | Δρmin = −0.94 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 > 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 | ||
C1 | 0.4571 (7) | 0.5495 (10) | 0.3857 (2) | 0.0287 (15) | |
C2 | 0.5860 (10) | 0.5823 (15) | 0.4020 (3) | 0.052 (2) | |
H2 | 0.6509 | 0.5469 | 0.3846 | 0.062* | |
C3 | 0.6180 (14) | 0.6670 (16) | 0.4437 (4) | 0.070 (3) | |
H3 | 0.704 | 0.6891 | 0.455 | 0.084* | |
C4 | 0.5215 (18) | 0.7165 (16) | 0.4674 (4) | 0.078 (4) | |
C5 | 0.3931 (16) | 0.6915 (18) | 0.4527 (3) | 0.078 (4) | |
H5 | 0.3296 | 0.7311 | 0.4703 | 0.093* | |
C6 | 0.3601 (10) | 0.6044 (14) | 0.4102 (3) | 0.051 (2) | |
H6 | 0.2738 | 0.5846 | 0.399 | 0.061* | |
N1 | 0.5170 (6) | 0.2609 (9) | 0.3281 (2) | 0.0274 (13) | |
O1 | 0.4650 (4) | 0.5891 (8) | 0.29942 (16) | 0.0280 (11) | |
O2 | 0.2871 (5) | 0.4018 (9) | 0.32575 (17) | 0.0350 (12) | |
O3W | 0 | 0.4971 (10) | 0.25 | 0.0273 (15) | |
H31 | 0.000 (8) | 0.541 (12) | 0.2754 (12) | 0.033* | |
O4W | 0.2379 (5) | −0.0996 (8) | 0.28949 (18) | 0.0339 (12) | |
H41 | 0.183 (5) | −0.158 (12) | 0.302 (2) | 0.041* | |
H42 | 0.307 (4) | −0.102 (13) | 0.306 (2) | 0.041* | |
Na1 | 0.1560 (3) | 0.2298 (4) | 0.26819 (9) | 0.0285 (6) | |
S1 | 0.42385 (15) | 0.4474 (3) | 0.33121 (5) | 0.0214 (4) | |
F1 | 0.5471 (12) | 0.7988 (13) | 0.5096 (2) | 0.141 (4) | |
Br1 | 0.48476 (9) | 0.06776 (13) | 0.37091 (3) | 0.0481 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.046 (4) | 0.018 (3) | 0.022 (3) | 0.006 (3) | 0.001 (3) | 0.001 (3) |
C2 | 0.059 (6) | 0.054 (6) | 0.037 (5) | −0.011 (5) | −0.016 (4) | 0.000 (4) |
C3 | 0.107 (10) | 0.041 (6) | 0.051 (6) | −0.006 (6) | −0.035 (6) | −0.006 (5) |
C4 | 0.150 (13) | 0.035 (6) | 0.040 (6) | −0.003 (7) | −0.025 (7) | −0.002 (5) |
C5 | 0.139 (12) | 0.064 (7) | 0.036 (5) | 0.024 (8) | 0.038 (7) | −0.003 (5) |
C6 | 0.067 (6) | 0.051 (6) | 0.039 (5) | 0.014 (5) | 0.020 (4) | 0.000 (4) |
N1 | 0.031 (3) | 0.021 (3) | 0.032 (3) | 0.010 (3) | 0.008 (2) | 0.004 (2) |
O1 | 0.027 (2) | 0.028 (3) | 0.029 (2) | 0.000 (2) | 0.0027 (19) | 0.009 (2) |
O2 | 0.022 (2) | 0.042 (3) | 0.040 (3) | −0.002 (2) | 0.001 (2) | 0.001 (2) |
O3W | 0.038 (4) | 0.021 (3) | 0.023 (3) | 0 | 0.006 (3) | 0 |
O4W | 0.020 (2) | 0.032 (3) | 0.050 (3) | 0.001 (2) | 0.007 (2) | 0.003 (2) |
Na1 | 0.0212 (13) | 0.0253 (15) | 0.0383 (15) | −0.0031 (11) | 0.0001 (11) | 0.0013 (12) |
S1 | 0.0207 (8) | 0.0201 (8) | 0.0230 (8) | −0.0002 (6) | 0.0006 (6) | 0.0019 (6) |
F1 | 0.275 (13) | 0.089 (6) | 0.045 (4) | 0.023 (7) | −0.039 (5) | −0.030 (4) |
Br1 | 0.0596 (6) | 0.0303 (4) | 0.0524 (5) | −0.0024 (4) | −0.0012 (4) | 0.0134 (4) |
C1—C6 | 1.365 (11) | O1—S1 | 1.444 (5) |
C1—C2 | 1.388 (12) | O1—Na1i | 2.442 (5) |
C1—S1 | 1.764 (7) | O1—Na1ii | 2.478 (5) |
C2—C3 | 1.374 (13) | O2—S1 | 1.445 (5) |
C2—H2 | 0.93 | O2—Na1 | 2.367 (6) |
C3—C4 | 1.338 (19) | O3W—Na1 | 2.435 (6) |
C3—H3 | 0.93 | O3W—H31 | 0.81 (5) |
C4—C5 | 1.366 (19) | O4W—Na1 | 2.425 (6) |
C4—F1 | 1.373 (12) | O4W—H41 | 0.82 (5) |
C5—C6 | 1.402 (14) | O4W—H42 | 0.82 (5) |
C5—H5 | 0.93 | Na1—O4Wi | 2.438 (6) |
C6—H6 | 0.93 | Na1—Na1iii | 3.299 (5) |
N1—S1 | 1.591 (6) | Na1—Na1i | 4.091 (3) |
N1—Br1 | 1.879 (6) | Na1—H31 | 2.66 (8) |
C6—C1—C2 | 120.9 (8) | O2—Na1—O1v | 109.3 (2) |
C6—C1—S1 | 121.5 (7) | O4W—Na1—O1v | 80.03 (18) |
C2—C1—S1 | 117.5 (6) | O3W—Na1—O1v | 79.74 (16) |
C3—C2—C1 | 120.3 (11) | O4Wi—Na1—O1v | 153.4 (2) |
C3—C2—H2 | 119.9 | O1iv—Na1—O1v | 78.8 (2) |
C1—C2—H2 | 119.9 | O2—Na1—Na1iii | 134.46 (17) |
C4—C3—C2 | 117.8 (11) | O4W—Na1—Na1iii | 112.85 (14) |
C4—C3—H3 | 121.1 | O3W—Na1—Na1iii | 47.37 (13) |
C2—C3—H3 | 121.1 | O4Wi—Na1—Na1iii | 106.01 (17) |
C3—C4—C5 | 124.3 (10) | O1iv—Na1—Na1iii | 48.35 (13) |
C3—C4—F1 | 120.7 (14) | O1v—Na1—Na1iii | 47.43 (13) |
C5—C4—F1 | 115.0 (15) | O2—Na1—Na1iv | 109.86 (17) |
C4—C5—C6 | 118.0 (11) | O4W—Na1—Na1iv | 32.82 (13) |
C4—C5—H5 | 121 | O3W—Na1—Na1iv | 150.46 (15) |
C6—C5—H5 | 121 | O4Wi—Na1—Na1iv | 85.78 (17) |
C1—C6—C5 | 118.6 (10) | O1iv—Na1—Na1iv | 71.32 (14) |
C1—C6—H6 | 120.7 | O1v—Na1—Na1iv | 102.55 (14) |
C5—C6—H6 | 120.7 | Na1iii—Na1—Na1iv | 113.24 (9) |
S1—N1—Br1 | 110.0 (3) | O2—Na1—Na1i | 62.71 (15) |
S1—O1—Na1i | 129.4 (3) | O4W—Na1—Na1i | 130.67 (17) |
S1—O1—Na1ii | 144.2 (3) | O3W—Na1—Na1i | 70.39 (11) |
Na1i—O1—Na1ii | 84.22 (17) | O4Wi—Na1—Na1i | 32.63 (14) |
S1—O2—Na1 | 131.4 (3) | O1iv—Na1—Na1i | 108.21 (17) |
Na1iii—O3W—Na1 | 85.3 (3) | O1v—Na1—Na1i | 147.25 (16) |
Na1iii—O3W—H31 | 114 (6) | Na1iii—Na1—Na1i | 113.24 (9) |
Na1—O3W—H31 | 97 (6) | Na1iv—Na1—Na1i | 110.02 (12) |
Na1—O4W—Na1iv | 114.6 (2) | O2—Na1—H31 | 82.2 (12) |
Na1—O4W—H41 | 108 (6) | O4W—Na1—H31 | 152.8 (15) |
Na1iv—O4W—H41 | 120 (6) | O3W—Na1—H31 | 17.7 (8) |
Na1—O4W—H42 | 116 (6) | O4Wi—Na1—H31 | 91.2 (16) |
Na1iv—O4W—H42 | 88 (6) | O1iv—Na1—H31 | 96.3 (11) |
H41—O4W—H42 | 109 (3) | O1v—Na1—H31 | 75.3 (18) |
O2—Na1—O4W | 95.6 (2) | Na1iii—Na1—H31 | 56.2 (15) |
O2—Na1—O3W | 96.66 (19) | Na1iv—Na1—H31 | 167.6 (10) |
O4W—Na1—O3W | 158.9 (2) | Na1i—Na1—H31 | 72.2 (18) |
O2—Na1—O4Wi | 90.9 (2) | O1—S1—O2 | 115.4 (3) |
O4W—Na1—O4Wi | 116.02 (17) | O1—S1—N1 | 104.4 (3) |
O3W—Na1—O4Wi | 80.89 (16) | O2—S1—N1 | 115.2 (3) |
O2—Na1—O1iv | 170.9 (2) | O1—S1—C1 | 108.2 (3) |
O4W—Na1—O1iv | 89.8 (2) | O2—S1—C1 | 105.7 (3) |
O3W—Na1—O1iv | 80.45 (17) | N1—S1—C1 | 107.7 (3) |
O4Wi—Na1—O1iv | 80.09 (19) | ||
C6—C1—C2—C3 | 1.5 (14) | Na1iii—O3W—Na1—O4Wi | 121.82 (17) |
S1—C1—C2—C3 | 178.1 (8) | Na1iii—O3W—Na1—O1iv | 40.44 (13) |
C1—C2—C3—C4 | −0.3 (16) | Na1iii—O3W—Na1—O1v | −39.84 (12) |
C2—C3—C4—C5 | −1.1 (18) | Na1iii—O3W—Na1—Na1iv | 57.5 (2) |
C2—C3—C4—F1 | 179.0 (10) | Na1iii—O3W—Na1—Na1i | 153.79 (13) |
C3—C4—C5—C6 | 1.4 (18) | Na1i—O1—S1—O2 | −9.1 (5) |
F1—C4—C5—C6 | −178.7 (9) | Na1ii—O1—S1—O2 | −165.6 (5) |
C2—C1—C6—C5 | −1.2 (13) | Na1i—O1—S1—N1 | 118.3 (4) |
S1—C1—C6—C5 | −177.6 (8) | Na1ii—O1—S1—N1 | −38.2 (6) |
C4—C5—C6—C1 | −0.2 (16) | Na1i—O1—S1—C1 | −127.2 (4) |
S1—O2—Na1—O4W | 73.4 (5) | Na1ii—O1—S1—C1 | 76.3 (6) |
S1—O2—Na1—O3W | −123.8 (4) | Na1—O2—S1—O1 | 68.3 (5) |
S1—O2—Na1—O1v | 154.8 (4) | Na1—O2—S1—N1 | −53.5 (5) |
S1—O2—Na1—Na1iii | −156.5 (3) | Na1—O2—S1—C1 | −172.3 (4) |
S1—O2—Na1—Na1iv | 43.0 (5) | Br1—N1—S1—O1 | 175.7 (3) |
Na1iv—O4W—Na1—O2 | −118.5 (2) | Br1—N1—S1—O2 | −56.8 (4) |
Na1iv—O4W—Na1—O3W | 116.1 (5) | Br1—N1—S1—C1 | 60.9 (4) |
Na1iv—O4W—Na1—O4Wi | −24.8 (2) | C6—C1—S1—O1 | 112.3 (7) |
Na1iv—O4W—Na1—O1iv | 54.1 (2) | C2—C1—S1—O1 | −64.2 (7) |
Na1iv—O4W—Na1—O1v | 132.8 (3) | C6—C1—S1—O2 | −11.8 (8) |
Na1iv—O4W—Na1—Na1iii | 97.9 (2) | C2—C1—S1—O2 | 171.7 (7) |
Na1iv—O4W—Na1—Na1i | −60.1 (3) | C6—C1—S1—N1 | −135.4 (7) |
Na1iii—O3W—Na1—O2 | −148.33 (19) | C2—C1—S1—N1 | 48.1 (7) |
Na1iii—O3W—Na1—O4W | −23.1 (5) |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x+1/2, y+1/2, z; (iii) −x, y, −z+1/2; (iv) −x+1/2, y−1/2, −z+1/2; (v) x−1/2, y−1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3W—H31···N1vi | 0.81 (5) | 2.15 (4) | 2.916 (7) | 157 (8) |
O4W—H41···N1v | 0.82 (5) | 2.05 (3) | 2.846 (8) | 165 (8) |
Symmetry codes: (v) x−1/2, y−1/2, z; (vi) x−1/2, y+1/2, z. |
Experimental details
Crystal data | |
Chemical formula | Na+·C6H4BrFNO2S−·1.5H2O |
Mr | 303.09 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 299 |
a, b, c (Å) | 10.3985 (8), 6.7027 (4), 29.892 (2) |
β (°) | 96.710 (8) |
V (Å3) | 2069.1 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 4.22 |
Crystal size (mm) | 0.44 × 0.34 × 0.15 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur |
Absorption correction | Analytical (CrysAlis RED; Oxford Diffraction, 2006) using a multifaceted crystal model (Clark & Reid, 1995) |
Tmin, Tmax | 0.187, 0.561 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6114, 2009, 1798 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.070, 0.151, 1.04 |
No. of reflections | 2009 |
No. of parameters | 141 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + (0.021P)2 + 67.2P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.60, −0.94 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97, PLATON (Spek, 2003) and WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O3W—H31···N1i | 0.81 (5) | 2.15 (4) | 2.916 (7) | 157 (8) |
O4W—H41···N1ii | 0.82 (5) | 2.05 (3) | 2.846 (8) | 165 (8) |
Symmetry codes: (i) x−1/2, y+1/2, z; (ii) x−1/2, y−1/2, z. |
The chemistry of N-bromo-arylsulfonamides is of interest due to their distinct physical, chemical and biological properties (Usha & Gowda, 2006). In the present work, the structure of sodium N-bromo-4-fluoro- benzenesulfonamidate (NaNB4FBSA) has been determined to study the substituent effects on the solid state structures of arylsulfonamides and N-halo arylsulfonamidates (Gowda, Jyothi et al., 2007; Gowda et al., 2007a,b; Gowda, Usha et al., 2007). The structure of NaNB4FBSA (Fig. 1) is similar to those of sodium N-bromo-benzenesulfonamidate(NaNBBSA)(Gowda, Usha et al., 2007) and sodium N-bromo-4-chloro-benzenesulfonamidate (NaNB4CBSA)(Gowda, Kožíšek et al., 2007a) and sodium N-chloro-arylsulfonamidates (George et al., 2000; Gowda, Jyothi et al., 2007). NaNB4FBSA crystallizes with two cations, two anions and three water molecules in the asymmetric unit. The sodium ion shows octahedral coordination by three O atoms of three different water molecules and by three sulfonyl O atoms of three different N-bromo-4-fluoro-benzenesulfonamide anions. There is no interaction between the nitrogen and sodium ions in the molecule. The S—N distances of N1—S1, 1.591 (6) Å is consistent with a S—N double bond and in agreement with those observed with NaNBBSA, NaNB4CBSA and sodium N-chloro- arylsulfonamidates. The occurrence of O—H···N hydrogen bonds between the wat er molecules and N atom associated with the presence of Na+ result in the formation of thick layered structure parallel to the (0 0 1) plane (Table 1, Fig. 1). This thick layer may be described as build up from an internal layer containing Na atoms and water molecules sandwiched by the benzenesulfonamidate with the fluorobenzene pointing outward.