Literature DB >> 21581218

Sodium 2-iodo-benzene-sulfonate monohydrate.

Muhammad Nadeem Arshad, M Nawaz Tahir, Islam Ullah Khan, Muhammad Shafiq, Waseeq Ahmad Siddiqui.   

Abstract

In the title compound, Na(+)·C(6)H(4)IO(3)S(-)·H(2)O, the Na atom is hexa-coordinated by O atoms, forming a two-dimensional sheet-like structure in the bc plane, with the iodo-benzene rings protruding above and below. Na⋯O contact distances are in the range 2.419 (2)-2.7218 (18) Å and O⋯Na⋯O angles are in the range 73.70 (5)-158.64 (7)°. The crystal structure is stabilized by O-H⋯O and C-H⋯O hydrogen bonds and C-H⋯π inter-actions. The I atom is disordered over two positions with occupancies of 0.78 (2) and 0.22 (2).

Entities:  

Year:  2008        PMID： 21581218      PMCID： PMC2960107          DOI： 10.1107/S1600536808039202

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


Related literature

For related literature on the synthesis of biologically active benzothia­zine derivatives, see: Arshad et al. (2008 ▶); Chau & Kice (1977 ▶); Shafiq, Khan et al. (2008 ▶); Shafiq, Tahir et al. (2008 ▶); Tahir et al. (2008 ▶).

Experimental

Crystal data

Na+·C6H4IO3S−·H2O M = 324.06 Monoclinic, a = 13.6141 (4) Å b = 8.8233 (3) Å c = 7.8493 (3) Å β = 92.171 (1)° V = 942.19 (6) Å3 Z = 4 Mo Kα radiation μ = 3.64 mm−1 T = 296 (2) K 0.25 × 0.17 × 0.15 mm

Data collection

Bruker KAPPA APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.482, T max = 0.580 10141 measured reflections 2339 independent reflections 2135 reflections with I > 2σ(I) R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.019 wR(F 2) = 0.047 S = 1.05 2339 reflections 128 parameters H-atom parameters constrained Δρmax = 0.41 e Å−3 Δρmin = −0.42 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039202/su2075sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039202/su2075Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Na+·C6H4IO3S–·H2OF000 = 616
Mr = 324.06Dx = 2.285 Mg m−3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2339 reflections
a = 13.6141 (4) Åθ = 1.5–28.3º
b = 8.8233 (3) ŵ = 3.64 mm−1
c = 7.8493 (3) ÅT = 296 (2) K
β = 92.171 (1)ºPrismatic, colorless
V = 942.19 (6) Å30.25 × 0.17 × 0.15 mm
Z = 4
Bruker KAPPA APEXII CCD diffractometer2339 independent reflections
Radiation source: fine-focus sealed tube2135 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.024
Detector resolution: 7.40 pixels mm-1θmax = 28.3º
T = 296(2) Kθmin = 1.5º
ω scansh = −18→18
Absorption correction: multi-scan(SADABS; Bruker, 2005)k = −11→11
Tmin = 0.482, Tmax = 0.580l = −10→10
10141 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.019H-atom parameters constrained
wR(F2) = 0.047  w = 1/[σ2(Fo2) + (0.0176P)2 + 0.7234P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.009
2339 reflectionsΔρmax = 0.42 e Å−3
128 parametersΔρmin = −0.42 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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*/UeqOcc. (<1)
I1A0.19343 (9)−0.1923 (2)0.55095 (18)0.0385 (2)0.78 (2)
I1B0.1984 (5)−0.1716 (17)0.5644 (12)0.0628 (13)0.22 (2)
S10.37585 (3)0.02639 (5)0.34970 (6)0.0236 (1)
Na0.51091 (7)0.29771 (10)0.49492 (12)0.0402 (3)
O10.42883 (11)0.14214 (18)0.2606 (2)0.0369 (5)
O20.38308 (12)0.0514 (2)0.53146 (19)0.0461 (6)
O30.40017 (11)−0.12539 (18)0.2976 (2)0.0390 (5)
O40.39172 (13)0.4952 (2)0.38765 (19)0.0413 (5)
C10.24956 (13)0.0530 (2)0.2877 (2)0.0227 (5)
C20.17328 (14)−0.0292 (2)0.3573 (2)0.0251 (5)
C30.07722 (15)−0.0064 (3)0.2991 (3)0.0328 (6)
C40.05587 (16)0.0976 (3)0.1724 (3)0.0386 (7)
C50.13033 (18)0.1803 (3)0.1044 (3)0.0412 (7)
C60.22673 (16)0.1593 (3)0.1618 (3)0.0332 (6)
H30.02673−0.061650.345900.0393*
H4−0.008750.111810.132990.0463*
H4A0.386450.486430.280180.0496*
H4B0.334950.516830.416580.0496*
H50.115860.250880.019140.0495*
H60.276530.216670.115780.0398*
U11U22U33U12U13U23
I1A0.0425 (3)0.0384 (5)0.0345 (3)−0.0046 (4)0.0010 (2)0.0146 (3)
I1B0.0625 (16)0.071 (3)0.0543 (18)−0.0264 (19)−0.0055 (11)0.0310 (15)
S10.0214 (2)0.0248 (2)0.0243 (2)0.0002 (2)−0.0019 (2)−0.0017 (2)
Na0.0466 (5)0.0325 (5)0.0407 (5)0.0011 (4)−0.0087 (4)−0.0053 (4)
O10.0285 (7)0.0346 (8)0.0478 (9)−0.0059 (6)0.0027 (6)0.0055 (7)
O20.0349 (8)0.0784 (13)0.0245 (7)−0.0004 (8)−0.0055 (6)−0.0061 (8)
O30.0301 (8)0.0252 (8)0.0612 (10)0.0051 (6)−0.0043 (7)−0.0076 (7)
O40.0447 (9)0.0519 (10)0.0274 (7)0.0000 (8)0.0018 (7)−0.0009 (7)
C10.0224 (8)0.0227 (9)0.0227 (8)0.0025 (7)−0.0012 (7)−0.0016 (7)
C20.0277 (9)0.0240 (9)0.0234 (9)0.0001 (7)−0.0006 (7)−0.0011 (7)
C30.0261 (9)0.0349 (12)0.0373 (11)−0.0030 (8)0.0008 (8)−0.0037 (9)
C40.0283 (10)0.0430 (13)0.0438 (12)0.0083 (9)−0.0091 (9)−0.0036 (10)
C50.0405 (12)0.0413 (14)0.0413 (12)0.0096 (10)−0.0066 (10)0.0141 (10)
C60.0333 (10)0.0316 (11)0.0346 (11)0.0019 (8)0.0017 (8)0.0091 (9)
I1A—C22.104 (2)O4—H4B0.8400
I1B—C22.073 (12)O4—H4A0.8500
S1—O11.4459 (16)C1—C61.389 (3)
S1—O21.4433 (16)C1—C21.395 (3)
S1—O31.4424 (16)C2—C31.384 (3)
S1—C11.7846 (18)C3—C41.376 (4)
Na—O12.5219 (18)C4—C51.373 (3)
Na—O42.505 (2)C5—C61.384 (3)
Na—O3i2.7218 (18)C3—H30.9300
Na—O3ii2.5060 (18)C4—H40.9300
Na—O4iii2.419 (2)C5—H50.9300
Na—O1iv2.4609 (18)C6—H60.9300
I1A···O23.368 (2)O4···O1iv3.191 (2)
I1A···O33.557 (2)O4···O1i3.036 (2)
I1A···C1v3.750 (2)O1···H4Aviii2.8900
I1A···I1Avi4.055 (2)O1···H62.4200
I1A···I1Av4.055 (2)O2···H6iv2.6100
I1A···C2v3.456 (2)O2···H4Aiv1.9800
I1A···C3v3.688 (3)C1···I1Avi3.750 (2)
I1B···O33.540 (8)C1···I1Bvi3.846 (14)
I1B···O23.211 (11)C2···I1Avi3.456 (2)
I1B···C3v3.797 (13)C2···I1Bvi3.526 (13)
I1B···C1v3.846 (14)C3···I1Avi3.688 (3)
I1B···C2v3.526 (13)C3···I1Bvi3.797 (13)
I1A···H4vii3.3300C4···C4x3.506 (3)
S1···O2ii3.4468 (17)C2···H5iv2.8900
O1···O3i3.149 (2)C3···H5iv2.8800
O1···O4viii3.036 (2)C4···H4x3.0700
O1···O4ix3.191 (2)C6···H4Bix2.9200
O2···S1ii3.4468 (17)H4···I1Axi3.3300
O2···I1B3.211 (11)H4···C4x3.0700
O2···I1A3.368 (2)H4A···O2ix1.9800
O2···O4iv2.824 (2)H4B···C6iv2.9200
O3···I1B3.540 (8)H5···C2ix2.8900
O3···O1viii3.149 (2)H5···C3ix2.8800
O3···I1A3.557 (2)H6···O12.4200
O4···O2ix2.824 (2)H6···O2ix2.6100
O1—S1—O2110.70 (10)Na—O4—Naiii93.37 (7)
O1—S1—O3113.24 (9)Naiii—O4—H4A118.00
O1—S1—C1105.56 (9)Naiii—O4—H4B103.00
O2—S1—O3114.48 (10)Na—O4—H4A107.00
O2—S1—C1106.16 (9)Na—O4—H4B131.00
O3—S1—C1105.90 (9)H4A—O4—H4B104.00
O1—Na—O482.53 (6)C2—C1—C6118.68 (17)
O1—Na—O3i73.70 (5)S1—C1—C6118.04 (14)
O1—Na—O3ii109.48 (6)S1—C1—C2123.27 (13)
O1—Na—O4iii155.53 (7)I1A—C2—C3115.71 (15)
O1—Na—O1iv122.18 (6)I1A—C2—C1124.06 (14)
O3i—Na—O481.15 (6)I1B—C2—C3118.2 (2)
O3ii—Na—O4158.64 (7)C1—C2—C3120.23 (17)
O4—Na—O4iii86.63 (6)I1B—C2—C1121.3 (2)
O1iv—Na—O479.96 (6)C2—C3—C4120.5 (2)
O3i—Na—O3ii118.69 (6)C3—C4—C5119.8 (2)
O3i—Na—O4iii83.01 (6)C4—C5—C6120.5 (2)
O1iv—Na—O3i153.11 (6)C1—C6—C5120.4 (2)
O3ii—Na—O4iii88.08 (6)C2—C3—H3120.00
O1iv—Na—O3ii78.69 (6)C4—C3—H3120.00
O1iv—Na—O4iii76.94 (6)C3—C4—H4120.00
S1—O1—Na104.30 (8)C5—C4—H4120.00
S1—O1—Naix144.40 (10)C4—C5—H5120.00
Na—O1—Naix107.32 (6)C6—C5—H5120.00
S1—O3—Naviii125.79 (9)C1—C6—H6120.00
S1—O3—Naii119.31 (9)C5—C6—H6120.00
Naviii—O3—Naii100.23 (6)
O2—S1—O1—Na4.83 (11)O3i—Na—O4—Naiii−83.44 (6)
O2—S1—O1—Naix156.95 (15)O3ii—Na—O4—Naiii75.95 (19)
O3—S1—O1—Na−125.30 (9)O4iii—Na—O4—Naiii0.00 (7)
O3—S1—O1—Naix26.83 (19)O1iv—Na—O4—Naiii77.33 (6)
C1—S1—O1—Na119.29 (8)O1—Na—O3i—S1i136.29 (11)
C1—S1—O1—Naix−88.58 (16)O1—Na—O3i—Naix−1.72 (6)
O1—S1—O3—Naviii−18.05 (13)O4—Na—O3i—S1i51.55 (11)
O1—S1—O3—Naii112.93 (10)O4—Na—O3i—Naix−86.47 (6)
O2—S1—O3—Naviii−146.24 (10)O1—Na—O3ii—S1ii19.44 (12)
O2—S1—O3—Naii−15.26 (13)O1—Na—O3ii—Naiv−122.08 (6)
C1—S1—O3—Naviii97.16 (10)O4—Na—O3ii—S1ii141.17 (16)
C1—S1—O3—Naii−131.86 (9)O4—Na—O3ii—Naiv−0.4 (2)
O1—S1—C1—C2−174.65 (15)O1—Na—O4iii—Naiii63.66 (18)
O1—S1—C1—C66.44 (18)O4—Na—O4iii—Naiii0.00 (6)
O2—S1—C1—C2−57.08 (17)O1—Na—O1iv—S1iv−100.39 (17)
O2—S1—C1—C6124.01 (17)O1—Na—O1iv—Naiv107.94 (8)
O3—S1—C1—C265.01 (16)O4—Na—O1iv—S1iv−25.90 (16)
O3—S1—C1—C6−113.91 (17)O4—Na—O1iv—Naiv−177.57 (7)
O4—Na—O1—S1−111.84 (9)S1—C1—C2—I1A2.0 (2)
O4—Na—O1—Naix84.73 (7)S1—C1—C2—C3−177.78 (16)
O3i—Na—O1—S1165.24 (9)C6—C1—C2—I1A−179.11 (16)
O3i—Na—O1—Naix1.81 (6)C6—C1—C2—C31.1 (3)
O3ii—Na—O1—S149.96 (10)S1—C1—C6—C5177.54 (18)
O3ii—Na—O1—Naix−113.48 (7)C2—C1—C6—C5−1.4 (3)
O4iii—Na—O1—S1−176.30 (14)I1A—C2—C3—C4−179.9 (2)
O4iii—Na—O1—Naix20.27 (19)C1—C2—C3—C4−0.1 (3)
O1iv—Na—O1—S1−38.71 (11)C2—C3—C4—C5−0.6 (4)
O1iv—Na—O1—Naix157.85 (7)C3—C4—C5—C60.3 (4)
O1—Na—O4—Naiii−158.02 (6)C4—C5—C6—C10.7 (4)
D—H···AD—HH···AD···AD—H···A
O4—H4A···O2ix0.851.982.824 (2)174
C6—H6···O10.932.422.834 (3)107
C5—H5···Cgix0.932.793.661 (3)156
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O4—H4A⋯O2i0.851.982.824 (2)174
C6—H6⋯O10.932.422.834 (3)107
C5—H5⋯Cgi0.932.793.661 (3)156

Symmetry code: (i) . Cg is the centroid of the benzene ring.

  5 in total

1.  A short history of SHELX.

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2.  1-Methyl-1H-2,1-benzothia-zin-4(3H)-one 2,2-dioxide.

Authors:  M Nawaz Tahir; Muhammad Shafiq; Islam Ullah Khan; Waseeq Ahmad Siddiqui; Muhammad Nadeem Arshad
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-02-06

3.  3,3-Dibromo-1-ethyl-1H-2,1-benzo-thiazin-4(3H)-one 2,2-dioxide.

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4.  1-Ethyl-1H-2,1-benzothia-zin-4(3H)-one 2,2-dioxide.

Authors:  Muhammad Shafiq; Islam Ullah Khan; M Nawaz Tahir; Waseeq Ahmad Siddiqui
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-02-06

5.  Potassium 2-iodo-benzene-sulfonate monohydrate.

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  3 in total

1.  2-Chloro-5-(2-iodo-benzene-sulfonamido)-benzoic acid.

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3.  4-(2-Iodo-benzene-sulfonamido)benzoic acid monohydrate.

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  3 in total

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