Literature DB >> 21836866

Sodium N-bromo-2-chloro-benzene-sulfonamidate sesquihydrate.

B Thimme Gowda, Sabine Foro, K Shakuntala.   

Abstract

In the title compound, Na(+)·C(6)H(4)BrClNO(2)S(-)·1.5H(2)O, one water mol-ecule has crystallographically imposed twofold symmetry. The Na(+) cation shows a pseudo-octa-hedral coordination provided by three O atoms of water mol-ecules and three sulfonyl O atoms of different N-bromo-2-chloro-benzene-sulfonamidate anions. The S-N distance of 1.579 (6) Å is consistent with an S=N double-bond character. The crystal structure is stabilized by O-H⋯Br, O-H⋯N and O-H⋯O hydrogen bonds.

Entities:  

Year:  2011        PMID： 21836866      PMCID： PMC3152083          DOI： 10.1107/S160053681102071X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background to the chemistry of N-haloaryl­sulfonamides, see: Gowda & Shetty (2004 ▶); Usha & Gowda (2006 ▶). For our study of the effect of substituents on the structures of N-haloaryl­sulfonamides, see: Gowda, Kožíšek et al. (2007 ▶); Gowda, Usha et al. (2007 ▶). For related structures, see: George et al. (2000 ▶); Olmstead & Power (1986 ▶). For an isostructural compound, see: Gowda et al. (2010 ▶).

Experimental

Crystal data

Na+·C6H4BrClNO2S−·1.5H2O M = 319.53 Monoclinic, a = 11.200 (2) Å b = 6.728 (1) Å c = 28.304 (3) Å β = 100.94 (1)° V = 2094.0 (5) Å3 Z = 8 Mo Kα radiation μ = 4.41 mm−1 T = 293 K 0.34 × 0.30 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD area detector Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.316, T max = 0.578 7442 measured reflections 2147 independent reflections 1955 reflections with I > 2σ(I) R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.049 wR(F 2) = 0.128 S = 1.25 2147 reflections 141 parameters 4 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 2.27 e Å−3 Δρmin = −1.19 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681102071X/rz2602sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102071X/rz2602Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Na+·C6H4BrClNO2S−·1.5H2OF(000) = 1256
Mr = 319.53Dx = 2.027 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4107 reflections
a = 11.200 (2) Åθ = 2.9–27.8°
b = 6.728 (1) ŵ = 4.41 mm−1
c = 28.304 (3) ÅT = 293 K
β = 100.94 (1)°Prism, yellow
V = 2094.0 (5) Å30.34 × 0.30 × 0.14 mm
Z = 8
Oxford Diffraction Xcalibur diffractometer with Sapphire CCD area detector2147 independent reflections
Radiation source: fine-focus sealed tube1955 reflections with I > 2σ(I)
graphiteRint = 0.018
rotation method data acquisition using ω scansθmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)h = −13→13
Tmin = 0.316, Tmax = 0.578k = −8→7
7442 measured reflectionsl = −35→35
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H atoms treated by a mixture of independent and constrained refinement
S = 1.25w = 1/[σ2(Fo2) + (0.0182P)2 + 43.7119P] where P = (Fo2 + 2Fc2)/3
2147 reflections(Δ/σ)max = 0.001
141 parametersΔρmax = 2.27 e Å−3
4 restraintsΔρmin = −1.19 e Å−3
Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
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.
xyzUiso*/Ueq
C10.8143 (5)−0.3307 (9)0.6083 (2)0.0205 (12)
C20.6903 (6)−0.3509 (11)0.5927 (2)0.0311 (14)
H20.6375−0.31010.61250.037*
C30.6437 (7)−0.4309 (13)0.5480 (3)0.0433 (19)
H30.5600−0.44090.53770.052*
C40.7209 (8)−0.4957 (12)0.5187 (3)0.044 (2)
H40.6892−0.55080.48880.053*
C50.8449 (8)−0.4791 (11)0.5336 (3)0.0374 (17)
H50.8971−0.52430.51400.045*
C60.8919 (6)−0.3942 (9)0.5782 (2)0.0249 (13)
Br10.88260 (6)0.14784 (10)0.62206 (2)0.0312 (2)
N10.9583 (5)−0.0535 (8)0.66407 (18)0.0247 (11)
Na11.1437 (2)−0.5132 (4)0.73529 (9)0.0303 (6)
O10.7549 (4)−0.1730 (8)0.68272 (16)0.0324 (11)
O20.9370 (4)−0.3782 (7)0.69654 (15)0.0286 (10)
O31.2055 (4)−0.1890 (8)0.70471 (17)0.0335 (11)
H311.246 (5)−0.241 (12)0.687 (2)0.040*
H321.1325 (19)−0.199 (12)0.695 (2)0.040*
O41.0000−0.7830 (10)0.75000.0336 (16)
H410.979 (7)−0.861 (9)0.728 (2)0.040*
S10.86584 (13)−0.2281 (2)0.66713 (5)0.0198 (3)
Cl11.04842 (16)−0.3824 (3)0.59503 (7)0.0414 (5)
U11U22U33U12U13U23
C10.023 (3)0.017 (3)0.021 (3)0.001 (2)0.003 (2)0.002 (2)
C20.026 (3)0.033 (4)0.033 (3)0.004 (3)0.003 (3)0.000 (3)
C30.030 (4)0.050 (5)0.045 (4)−0.004 (4)−0.007 (3)−0.009 (4)
C40.056 (5)0.043 (5)0.027 (4)−0.005 (4)−0.009 (3)−0.010 (3)
C50.055 (5)0.032 (4)0.028 (4)−0.001 (3)0.017 (3)−0.005 (3)
C60.030 (3)0.020 (3)0.026 (3)0.000 (3)0.009 (3)0.002 (2)
Br10.0358 (4)0.0245 (3)0.0342 (4)0.0033 (3)0.0092 (3)0.0072 (3)
N10.022 (3)0.025 (3)0.025 (3)0.003 (2)0.001 (2)0.002 (2)
Na10.0299 (14)0.0312 (14)0.0320 (14)0.0047 (11)0.0114 (11)−0.0007 (11)
O10.030 (2)0.040 (3)0.030 (2)0.001 (2)0.0131 (19)−0.006 (2)
O20.033 (2)0.028 (2)0.023 (2)0.002 (2)0.0021 (18)0.0075 (19)
O30.027 (2)0.039 (3)0.034 (3)0.002 (2)0.006 (2)−0.003 (2)
O40.044 (4)0.024 (4)0.030 (4)0.0000.000 (3)0.000
S10.0209 (7)0.0215 (7)0.0170 (7)0.0005 (6)0.0038 (5)0.0002 (6)
Cl10.0280 (8)0.0478 (11)0.0522 (11)0.0018 (8)0.0174 (8)−0.0107 (9)
C1—C21.382 (9)Na1—O3iii2.459 (5)
C1—C61.393 (8)Na1—O32.493 (6)
C1—S11.793 (6)Na1—O42.512 (6)
C2—C31.383 (10)Na1—O22.534 (5)
C2—H20.9300Na1—S1ii3.381 (3)
C3—C41.378 (12)Na1—H322.40 (9)
C3—H30.9300O1—S11.444 (5)
C4—C51.378 (11)O1—Na1iv2.371 (5)
C4—H40.9300O2—S11.448 (5)
C5—C61.396 (9)O2—Na1ii2.455 (5)
C5—H50.9300O3—Na1v2.459 (5)
C6—Cl11.729 (7)O3—H310.82 (2)
Br1—N11.893 (5)O3—H320.81 (2)
N1—S11.579 (6)O4—Na1ii2.512 (6)
Na1—O1i2.371 (5)O4—H410.82 (2)
Na1—O2ii2.455 (5)S1—Na1ii3.381 (3)
C2—C1—C6118.6 (6)O2ii—Na1—S1ii22.28 (11)
C2—C1—S1117.5 (5)O3iii—Na1—S1ii80.37 (14)
C6—C1—S1123.9 (5)O3—Na1—S1ii80.85 (13)
C1—C2—C3120.9 (6)O4—Na1—S1ii98.86 (11)
C1—C2—H2119.6O2—Na1—S1ii88.99 (13)
C3—C2—H2119.6O1i—Na1—H3294.9 (14)
C4—C3—C2120.2 (7)O2ii—Na1—H3293.2 (15)
C4—C3—H3119.9O3iii—Na1—H32136.1 (7)
C2—C3—H3119.9O3—Na1—H3219.0 (5)
C5—C4—C3120.1 (7)O4—Na1—H32137.7 (5)
C5—C4—H4120.0O2—Na1—H3261.1 (5)
C3—C4—H4120.0S1ii—Na1—H3283.3 (15)
C4—C5—C6119.7 (7)S1—O1—Na1iv153.3 (3)
C4—C5—H5120.2S1—O2—Na1ii117.7 (3)
C6—C5—H5120.2S1—O2—Na1149.0 (3)
C1—C6—C5120.5 (6)Na1ii—O2—Na188.25 (17)
C1—C6—Cl1122.4 (5)Na1v—O3—Na1112.4 (2)
C5—C6—Cl1117.1 (5)Na1v—O3—H31104 (5)
S1—N1—Br1110.3 (3)Na1—O3—H3194 (6)
O1i—Na1—O2ii167.5 (2)Na1v—O3—H32142 (5)
O1i—Na1—O3iii80.89 (18)Na1—O3—H3274 (6)
O2ii—Na1—O3iii86.70 (18)H31—O3—H32112 (4)
O1i—Na1—O388.03 (19)Na1—O4—Na1ii87.5 (3)
O2ii—Na1—O396.71 (18)Na1—O4—H41116 (6)
O3iii—Na1—O3117.45 (15)Na1ii—O4—H41119 (6)
O1i—Na1—O4101.87 (19)O1—S1—O2114.5 (3)
O2ii—Na1—O478.11 (16)O1—S1—N1115.9 (3)
O3iii—Na1—O485.18 (16)O2—S1—N1104.8 (3)
O3—Na1—O4156.70 (19)O1—S1—C1103.8 (3)
O1i—Na1—O2115.86 (19)O2—S1—C1108.1 (3)
O2ii—Na1—O276.42 (19)N1—S1—C1109.5 (3)
O3iii—Na1—O2157.31 (19)O1—S1—Na1ii74.5 (2)
O3—Na1—O280.02 (17)N1—S1—Na1ii126.1 (2)
O4—Na1—O276.68 (15)C1—S1—Na1ii119.0 (2)
O1i—Na1—S1ii150.64 (16)
C6—C1—C2—C3−0.5 (10)O1i—Na1—O4—Na1ii−152.81 (18)
S1—C1—C2—C3−179.3 (6)O2ii—Na1—O4—Na1ii39.93 (12)
C1—C2—C3—C41.4 (12)O3iii—Na1—O4—Na1ii127.57 (16)
C2—C3—C4—C5−0.7 (13)O3—Na1—O4—Na1ii−39.3 (4)
C3—C4—C5—C6−0.8 (12)O2—Na1—O4—Na1ii−38.72 (11)
C2—C1—C6—C5−1.0 (10)S1ii—Na1—O4—Na1ii48.11 (6)
S1—C1—C6—C5177.7 (5)Na1iv—O1—S1—O273.2 (8)
C2—C1—C6—Cl1−178.1 (5)Na1iv—O1—S1—N1−49.0 (8)
S1—C1—C6—Cl10.6 (8)Na1iv—O1—S1—C1−169.1 (7)
C4—C5—C6—C11.6 (11)Na1iv—O1—S1—Na1ii74.1 (7)
C4—C5—C6—Cl1178.9 (6)Na1ii—O2—S1—O11.2 (4)
O1i—Na1—O2—S1−74.9 (6)Na1—O2—S1—O1−142.6 (5)
O2ii—Na1—O2—S1107.4 (5)Na1ii—O2—S1—N1129.4 (3)
O3iii—Na1—O2—S1150.4 (5)Na1—O2—S1—N1−14.4 (6)
O3—Na1—O2—S18.0 (6)Na1ii—O2—S1—C1−113.9 (3)
O4—Na1—O2—S1−171.8 (6)Na1—O2—S1—C1102.3 (6)
S1ii—Na1—O2—S188.9 (6)Na1—O2—S1—Na1ii−143.8 (7)
O1i—Na1—O2—Na1ii136.66 (17)Br1—N1—S1—O1−57.6 (4)
O2ii—Na1—O2—Na1ii−41.0 (2)Br1—N1—S1—O2175.1 (3)
O3iii—Na1—O2—Na1ii2.0 (6)Br1—N1—S1—C159.4 (4)
O3—Na1—O2—Na1ii−140.47 (18)Br1—N1—S1—Na1ii−146.92 (16)
O4—Na1—O2—Na1ii39.77 (14)C2—C1—S1—O1−5.0 (6)
S1ii—Na1—O2—Na1ii−59.58 (15)C6—C1—S1—O1176.3 (5)
O1i—Na1—O3—Na1v−108.3 (2)C2—C1—S1—O2117.0 (5)
O2ii—Na1—O3—Na1v60.1 (2)C6—C1—S1—O2−61.7 (6)
O3iii—Na1—O3—Na1v−29.7 (2)C2—C1—S1—N1−129.4 (5)
O4—Na1—O3—Na1v135.6 (4)C6—C1—S1—N151.9 (6)
O2—Na1—O3—Na1v135.0 (2)C2—C1—S1—Na1ii74.7 (5)
S1ii—Na1—O3—Na1v44.40 (17)C6—C1—S1—Na1ii−103.9 (5)
D—H···AD—HH···AD···AD—H···A
O3—H31···Br1i0.82 (2)2.70 (2)3.518 (5)171 (8)
O3—H32···N10.81 (2)2.21 (5)2.934 (7)149 (8)
O3—H32···O20.81 (2)2.51 (5)3.232 (7)148 (8)
O4—H41···N1vi0.82 (2)2.20 (3)3.002 (7)168 (8)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O3—H31⋯Br1i0.82 (2)2.70 (2)3.518 (5)171 (8)
O3—H32⋯N10.81 (2)2.21 (5)2.934 (7)149 (8)
O3—H32⋯O20.81 (2)2.51 (5)3.232 (7)148 (8)
O4—H41⋯N1ii0.82 (2)2.20 (3)3.002 (7)168 (8)

Symmetry codes: (i) ; (ii) .

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