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The structure of the dihydroxyphenylselenonium ion (C_{6}H_{7}O_{2}Se^{+}) has been determined in its benzenesulfonate (C_{6}H_{5}O_{3}Se^{-}) and p-toluenesulfonate (C_{7}H_{7}O_{3}S ^{-}) salts. Whereas the former salt is disordered, the latter less dense salt is well defined. This difference in crystallization behaviour is attributed to a C—H...O hydrogen bond involving the methyl group of the p-toluenesulfonate ion. The two salts display very similar hydrogen-bond arrangements and differ only with respect to the stacking of the phenyl groups. The dihydroxyselenonium ion is a strong acid with a pK value of −0.9 determined from the variation of the 77Se chemical shift. A comparison with the two deprotonated species reveals a systematic increase in the Se—O bond lengths and the pyramidal configuration around Se with the number of protons attached.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768100010697/os0057sup1.cif
Contains datablocks default, TOL, BEN

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100010697/os0057TOLsup2.hkl
Contains datablock TOL

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100010697/os0057BENsup3.hkl
Contains datablock BEN

CCDC references: 156661; 156662

Computing details top

For both compounds, data collection: Enraf-Nonius XPRESS; cell refinement: Enraf-Nonius XPRESS; data reduction: DREADD (Blessing, 1987); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976).

(TOL) dihydroxy phenylselenonium 4-methylphenyl sulfonate top
Crystal data top
C6H7O2Se+·C7H7O3SF(000) = 728
Mr = 361.26Dx = 1.705 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 5.8838 (11) ÅCell parameters from 23 reflections
b = 16.0925 (19) Åθ = 39.5–42.3°
c = 14.929 (2) ŵ = 5.17 mm1
β = 95.547 (15)°T = 122 K
V = 1407.0 (4) Å3Needle, colourless
Z = 40.36 × 0.08 × 0.07 mm
Data collection top
Enraf Nonius CAD-4
diffractometer
2820 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 74.9°, θmin = 4.1°
ω – 2θ scansh = 74
Absorption correction: numerical
(DeTitta, 1985)
k = 020
Tmin = 0.370, Tmax = 0.726l = 1818
5288 measured reflections5 standard reflections every 166.7 min
2906 independent reflections intensity decay: 9.9%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075All H-atom parameters refined
S = 2.39Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo2)]
2906 reflections(Δ/σ)max = 0.029
237 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.86 e Å3
Crystal data top
C6H7O2Se+·C7H7O3SV = 1407.0 (4) Å3
Mr = 361.26Z = 4
Monoclinic, P21/cCu Kα radiation
a = 5.8838 (11) ŵ = 5.17 mm1
b = 16.0925 (19) ÅT = 122 K
c = 14.929 (2) Å0.36 × 0.08 × 0.07 mm
β = 95.547 (15)°
Data collection top
Enraf Nonius CAD-4
diffractometer
2820 reflections with I > 2σ(I)
Absorption correction: numerical
(DeTitta, 1985)
Rint = 0.033
Tmin = 0.370, Tmax = 0.7265 standard reflections every 166.7 min
5288 measured reflections intensity decay: 9.9%
2906 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0270 restraints
wR(F2) = 0.075All H-atom parameters refined
S = 2.39Δρmax = 0.44 e Å3
2906 reflectionsΔρmin = 0.86 e Å3
237 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Se1.49991 (3)0.440382 (11)0.618334 (12)0.01292 (9)
O111.3405 (3)0.47988 (9)0.70046 (9)0.0189 (3)
H1101.248 (6)0.514 (2)0.677 (2)0.043 (9)*
O121.7698 (3)0.45573 (10)0.67323 (11)0.0202 (3)
H1201.806 (6)0.492 (2)0.656 (2)0.048 (11)*
C111.4822 (3)0.32727 (12)0.65740 (13)0.0153 (4)
C161.2894 (4)0.30150 (13)0.69657 (13)0.0190 (4)
H161.188 (4)0.3371 (16)0.7080 (17)0.023 (7)*
C151.2736 (4)0.21839 (14)0.72069 (14)0.0247 (5)
H151.136 (5)0.2013 (19)0.7503 (19)0.038 (8)*
C141.4465 (4)0.16344 (13)0.70460 (16)0.0279 (5)
H141.429 (5)0.110 (2)0.721 (2)0.041 (8)*
C131.6379 (4)0.19051 (13)0.66597 (16)0.0267 (5)
H131.765 (6)0.154 (2)0.647 (2)0.052 (9)*
C121.6578 (4)0.27328 (13)0.64188 (14)0.0190 (4)
H121.782 (4)0.2875 (16)0.6191 (16)0.020 (6)*
S1.93426 (8)0.37598 (3)1.44917 (3)0.01381 (11)
O211.6969 (2)0.38869 (9)1.46536 (9)0.0185 (3)
O221.9798 (2)0.41539 (9)1.36250 (10)0.0178 (3)
O232.0987 (3)0.40097 (9)1.52264 (10)0.0233 (3)
C211.9715 (3)0.26826 (11)1.43297 (12)0.0150 (4)
C261.7915 (4)0.22094 (13)1.39255 (14)0.0204 (4)
H261.657 (5)0.2461 (18)1.3746 (17)0.029 (7)*
C251.8240 (4)0.13718 (13)1.37779 (15)0.0244 (4)
H251.692 (4)0.1025 (16)1.3469 (17)0.024 (6)*
C242.0331 (4)0.09914 (12)1.40294 (14)0.0220 (4)
C232.2106 (4)0.14733 (14)1.44372 (15)0.0252 (5)
H232.354 (5)0.1252 (16)1.4607 (17)0.023 (6)*
C222.1811 (4)0.23179 (13)1.45846 (14)0.0213 (4)
H222.291 (5)0.2601 (19)1.4779 (19)0.035 (8)*
C272.0666 (6)0.00804 (15)1.38557 (18)0.0327 (6)
H27A1.937 (8)0.024 (3)1.400 (3)0.086 (14)*
H27B2.119 (7)0.002 (3)1.335 (3)0.074 (13)*
H27C2.206 (8)0.011 (3)1.421 (3)0.080 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se0.01197 (13)0.01193 (13)0.01490 (13)0.00112 (6)0.00158 (8)0.00137 (6)
O110.0202 (7)0.0184 (7)0.0186 (7)0.0052 (6)0.0042 (6)0.0003 (5)
O120.0142 (7)0.0207 (7)0.0253 (8)0.0046 (6)0.0012 (6)0.0064 (6)
C110.0163 (9)0.0132 (8)0.0161 (8)0.0002 (7)0.0009 (7)0.0023 (7)
C160.0168 (10)0.0195 (9)0.0205 (9)0.0010 (8)0.0015 (7)0.0020 (8)
C150.0234 (11)0.0255 (11)0.0242 (10)0.0100 (9)0.0024 (8)0.0069 (8)
C140.0348 (13)0.0139 (10)0.0328 (12)0.0043 (9)0.0081 (10)0.0078 (8)
C130.0265 (12)0.0173 (10)0.0347 (12)0.0069 (9)0.0048 (9)0.0013 (9)
C120.0151 (10)0.0178 (9)0.0235 (10)0.0020 (8)0.0000 (8)0.0014 (7)
S0.0121 (2)0.0117 (2)0.0176 (2)0.00103 (15)0.00140 (17)0.00106 (15)
O210.0135 (7)0.0181 (7)0.0246 (7)0.0023 (5)0.0052 (5)0.0004 (5)
O220.0175 (7)0.0137 (7)0.0230 (7)0.0000 (5)0.0062 (5)0.0020 (6)
O230.0211 (8)0.0197 (7)0.0273 (8)0.0023 (6)0.0064 (6)0.0080 (6)
C210.0169 (9)0.0122 (8)0.0161 (8)0.0012 (7)0.0029 (7)0.0005 (6)
C260.0183 (10)0.0190 (10)0.0233 (10)0.0009 (8)0.0010 (8)0.0005 (8)
C250.0316 (12)0.0172 (10)0.0244 (10)0.0045 (9)0.0022 (9)0.0018 (8)
C240.0365 (13)0.0133 (9)0.0172 (9)0.0035 (8)0.0080 (8)0.0010 (7)
C230.0264 (12)0.0217 (10)0.0278 (11)0.0110 (9)0.0037 (9)0.0003 (8)
C220.0173 (10)0.0198 (10)0.0262 (10)0.0024 (8)0.0008 (8)0.0027 (8)
C270.0557 (17)0.0162 (11)0.0277 (12)0.0054 (11)0.0115 (11)0.0009 (9)
Geometric parameters (Å, º) top
Se—O121.7331 (16)S—O211.4546 (14)
Se—O111.7350 (14)S—O221.4885 (14)
Se—C111.9173 (19)S—C211.7668 (19)
C11—C121.387 (3)C21—C221.385 (3)
C11—C161.389 (3)C21—C261.394 (3)
C16—C151.390 (3)C26—C251.382 (3)
C15—C141.386 (3)C25—C241.393 (3)
C14—C131.385 (3)C24—C231.393 (3)
C13—C121.387 (3)C24—C271.505 (3)
S—O231.4477 (15)C23—C221.390 (3)
O12—Se—O1198.46 (8)O23—S—C21107.08 (9)
O12—Se—C1193.76 (8)O21—S—C21107.12 (9)
O11—Se—C1194.81 (8)O22—S—C21105.31 (8)
C12—C11—C16122.37 (18)C22—C21—C26120.43 (19)
C12—C11—Se118.74 (15)C22—C21—S119.79 (15)
C16—C11—Se118.82 (15)C26—C21—S119.76 (15)
C11—C16—C15118.3 (2)C25—C26—C21119.4 (2)
C14—C15—C16120.0 (2)C26—C25—C24121.2 (2)
C13—C14—C15120.8 (2)C23—C24—C25118.59 (19)
C14—C13—C12120.2 (2)C23—C24—C27120.8 (2)
C11—C12—C13118.4 (2)C25—C24—C27120.6 (2)
O23—S—O21114.65 (9)C22—C23—C24120.9 (2)
O23—S—O22112.15 (9)C21—C22—C23119.5 (2)
O21—S—O22109.94 (8)
O12—Se—C11—C1252.97 (17)O22—S—C21—C2293.96 (17)
O11—Se—C11—C12151.80 (16)O23—S—C21—C26156.05 (16)
O12—Se—C11—C16129.87 (16)O21—S—C21—C2632.60 (18)
O11—Se—C11—C1631.04 (16)O22—S—C21—C2684.41 (18)
C12—C11—C16—C150.1 (3)C22—C21—C26—C250.2 (3)
Se—C11—C16—C15176.96 (15)S—C21—C26—C25178.17 (16)
C11—C16—C15—C140.7 (3)C21—C26—C25—C240.3 (3)
C16—C15—C14—C131.1 (3)C26—C25—C24—C230.1 (3)
C15—C14—C13—C120.7 (4)C26—C25—C24—C27179.4 (2)
C16—C11—C12—C130.5 (3)C25—C24—C23—C220.5 (3)
Se—C11—C12—C13176.58 (16)C27—C24—C23—C22178.9 (2)
C14—C13—C12—C110.1 (3)C26—C21—C22—C230.2 (3)
O23—S—C21—C2225.57 (19)S—C21—C22—C23178.60 (17)
O21—S—C21—C22149.03 (16)C24—C23—C22—C210.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O11—H110···O22i0.83 (3)1.81 (3)2.633 (2)172 (3)
O12—H120···O22ii0.68 (3)1.99 (3)2.628 (2)157 (4)
C27—H27B···O11iii0.84 (4)2.52 (4)3.337 (3)164 (4)
Symmetry codes: (i) x+3, y+1, z+2; (ii) x+4, y+1, z+2; (iii) x+1, y+1/2, z+1/2.
(BEN) dihydroxy phenylselenonium benzene sulfonate top
Crystal data top
C6H7O2Se+·C6H5O3SDx = 1.761 Mg m3
Mr = 347.24Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Fdd2Cell parameters from 20 reflections
a = 40.641 (5) Åθ = 39.1–40.6°
b = 22.268 (3) ŵ = 5.52 mm1
c = 5.7881 (13) ÅT = 122 K
V = 5238.4 (15) Å3Needle, colourless
Z = 160.36 × 0.08 × 0.07 mm
F(000) = 2784
Data collection top
Enraf Nonius CAD-4
diffractometer
2552 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
Graphite monochromatorθmax = 74.9°, θmin = 4.4°
ω – 2θ scansh = 5050
Absorption correction: numerical
(DeTitta, 1985)
k = 270
Tmin = 0.361, Tmax = 0.737l = 76
5592 measured reflections4 standard reflections every 166.7 min
2669 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.074H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.143Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo2)]
S = 5.84(Δ/σ)max = 0.036
2669 reflectionsΔρmax = 1.19 e Å3
166 parametersΔρmin = 1.13 e Å3
7 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (5)
Crystal data top
C6H7O2Se+·C6H5O3SV = 5238.4 (15) Å3
Mr = 347.24Z = 16
Orthorhombic, Fdd2Cu Kα radiation
a = 40.641 (5) ŵ = 5.52 mm1
b = 22.268 (3) ÅT = 122 K
c = 5.7881 (13) Å0.36 × 0.08 × 0.07 mm
Data collection top
Enraf Nonius CAD-4
diffractometer
2552 reflections with I > 2σ(I)
Absorption correction: numerical
(DeTitta, 1985)
Rint = 0.038
Tmin = 0.361, Tmax = 0.7374 standard reflections every 166.7 min
5592 measured reflections intensity decay: none
2669 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.074H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.143Δρmax = 1.19 e Å3
S = 5.84Δρmin = 1.13 e Å3
2669 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
166 parametersAbsolute structure parameter: 0.01 (5)
7 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Se0.00474 (2)0.09172 (4)0.0064 (3)0.0466 (3)
O110.02224 (13)0.1138 (2)0.2518 (14)0.0434 (14)
O120.03535 (13)0.1150 (3)0.1938 (11)0.056 (2)
C110.02233 (17)0.1620 (3)0.0373 (17)0.0313 (19)
C120.02132 (17)0.1957 (3)0.2348 (18)0.0316 (17)
H120.00610.18590.35350.038*
C130.0423 (2)0.2437 (3)0.262 (2)0.0371 (19)
H130.04180.26700.39960.045*
C140.0640 (2)0.2574 (3)0.0854 (17)0.039 (2)
H140.07840.29070.10100.047*
C150.0647 (2)0.2225 (3)0.1168 (16)0.0326 (19)
H150.07980.23190.23670.039*
C160.04363 (19)0.1752 (3)0.1404 (15)0.0317 (19)
H160.04370.15160.27730.038*
S0.05331 (5)0.02257 (9)0.4980 (5)0.0558 (8)
O21A0.0309 (3)0.0534 (5)0.3456 (19)0.0458 (14)*0.518 (8)
O22A0.0589 (3)0.0401 (3)0.470 (3)0.0458 (14)*0.518 (8)
O23A0.0392 (3)0.0195 (6)0.7308 (14)0.0458 (14)*0.518 (8)
O21B0.0283 (3)0.0660 (5)0.436 (2)0.0458 (14)*0.482 (8)
O22B0.0659 (3)0.0202 (5)0.327 (2)0.0458 (14)*0.482 (8)
O23B0.0467 (3)0.0107 (6)0.7049 (16)0.0458 (14)*0.482 (8)
C210.08864 (16)0.0674 (3)0.5451 (16)0.0276 (19)
C220.10690 (16)0.0622 (3)0.7457 (17)0.0292 (17)
H220.10100.03370.86040.035*
C230.13386 (17)0.0989 (3)0.7774 (17)0.0340 (19)
H230.14680.09520.91350.041*
C240.14224 (19)0.1412 (4)0.6122 (17)0.035 (2)
H240.16050.16710.63690.042*
C250.12387 (19)0.1457 (4)0.4095 (17)0.037 (2)
H250.12990.17450.29600.045*
C260.09723 (19)0.1091 (4)0.3716 (16)0.0321 (19)
H260.08490.11190.23260.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se0.0278 (4)0.0292 (4)0.0829 (7)0.0071 (4)0.0167 (6)0.0188 (6)
O110.040 (3)0.043 (3)0.048 (4)0.006 (3)0.012 (4)0.003 (4)
O120.021 (3)0.112 (6)0.035 (4)0.008 (3)0.003 (3)0.025 (4)
C110.027 (3)0.014 (3)0.054 (6)0.001 (3)0.005 (4)0.015 (4)
C120.028 (3)0.030 (4)0.037 (5)0.006 (3)0.002 (4)0.000 (4)
C130.048 (5)0.031 (4)0.032 (4)0.006 (3)0.012 (5)0.008 (4)
C140.044 (5)0.025 (4)0.049 (6)0.004 (4)0.007 (4)0.001 (4)
C150.032 (4)0.029 (4)0.037 (5)0.002 (3)0.007 (4)0.004 (4)
C160.036 (4)0.022 (4)0.037 (5)0.003 (3)0.004 (4)0.000 (4)
S0.0322 (10)0.0295 (10)0.106 (2)0.0074 (8)0.0327 (15)0.0197 (16)
C210.016 (3)0.023 (3)0.044 (6)0.003 (3)0.000 (4)0.001 (4)
C220.024 (3)0.027 (3)0.037 (5)0.005 (3)0.007 (4)0.007 (4)
C230.025 (4)0.036 (4)0.041 (5)0.002 (3)0.014 (4)0.006 (5)
C240.029 (4)0.026 (4)0.049 (6)0.006 (3)0.001 (4)0.000 (4)
C250.021 (4)0.046 (5)0.045 (6)0.003 (3)0.004 (4)0.013 (4)
C260.027 (4)0.032 (4)0.037 (5)0.004 (3)0.002 (4)0.003 (4)
Geometric parameters (Å, º) top
Se—O111.727 (7)S—O21A1.443 (6)
Se—O121.730 (6)S—O21B1.447 (6)
Se—C111.922 (7)S—O22B1.465 (6)
C11—C121.368 (13)S—O23A1.466 (6)
C11—C161.376 (11)S—C211.769 (7)
C12—C131.376 (11)C21—C221.383 (11)
C13—C141.384 (14)C21—C261.412 (12)
C14—C151.405 (11)C22—C231.380 (9)
C15—C161.366 (10)C23—C241.384 (12)
S—O22A1.424 (6)C24—C251.394 (13)
S—O23B1.434 (6)C25—C261.372 (11)
O11—Se—O1299.3 (3)O21B—S—O22B120.7 (8)
O11—Se—C1194.8 (3)O22A—S—O23A96.9 (8)
O12—Se—C1196.2 (3)O23B—S—O23A30.1 (6)
C12—C11—C16121.8 (7)O21A—S—O23A109.7 (7)
C12—C11—Se120.5 (6)O21B—S—O23A89.1 (8)
C16—C11—Se117.6 (6)O22B—S—O23A136.6 (8)
C11—C12—C13120.2 (9)O22A—S—C21116.2 (5)
C12—C13—C14118.7 (10)O23B—S—C21108.4 (7)
C13—C14—C15120.5 (8)O21A—S—C21109.8 (6)
C16—C15—C14119.8 (8)O21B—S—C21103.4 (6)
C15—C16—C11119.0 (8)O22B—S—C21100.8 (6)
O22A—S—O23B67.5 (8)O23A—S—C21101.7 (6)
O22A—S—O21A119.8 (7)C22—C21—C26121.3 (7)
O23B—S—O21A129.6 (8)C22—C21—S121.2 (6)
O22A—S—O21B137.5 (8)C26—C21—S117.5 (6)
O23B—S—O21B114.9 (8)C23—C22—C21119.2 (8)
O21A—S—O21B24.1 (7)C22—C23—C24120.4 (8)
O22A—S—O22B39.7 (7)C23—C24—C25119.9 (7)
O23B—S—O22B107.0 (7)C26—C25—C24120.9 (8)
O21A—S—O22B96.7 (7)C25—C26—C21118.2 (8)
O11—Se—C11—C12126.6 (6)O22B—S—C21—C22105.8 (8)
O12—Se—C11—C1226.7 (6)O23B—S—C21—C226.4 (9)
O11—Se—C11—C1656.5 (6)O21A—S—C21—C2626.2 (9)
O12—Se—C11—C16156.4 (6)O22A—S—C21—C26113.8 (9)
C16—C11—C12—C131.0 (12)O23A—S—C21—C26142.3 (8)
Se—C11—C12—C13175.8 (6)O21B—S—C21—C2650.4 (9)
C11—C12—C13—C140.7 (12)O22B—S—C21—C2675.0 (8)
C12—C13—C14—C150.6 (13)O23B—S—C21—C26172.7 (8)
C13—C14—C15—C160.7 (13)C26—C21—C22—C230.5 (11)
C14—C15—C16—C111.0 (13)S—C21—C22—C23178.6 (6)
C12—C11—C16—C151.1 (12)C21—C22—C23—C241.1 (12)
Se—C11—C16—C15175.7 (6)C22—C23—C24—C251.7 (12)
O21A—S—C21—C22153.0 (8)C23—C24—C25—C260.7 (13)
O22A—S—C21—C2267.0 (10)C24—C25—C26—C210.9 (12)
O23A—S—C21—C2236.8 (8)C22—C21—C26—C251.5 (11)
O21B—S—C21—C22128.7 (8)S—C21—C26—C25177.7 (6)

Experimental details

(TOL)(BEN)
Crystal data
Chemical formulaC6H7O2Se+·C7H7O3SC6H7O2Se+·C6H5O3S
Mr361.26347.24
Crystal system, space groupMonoclinic, P21/cOrthorhombic, Fdd2
Temperature (K)122122
a, b, c (Å)5.8838 (11), 16.0925 (19), 14.929 (2)40.641 (5), 22.268 (3), 5.7881 (13)
α, β, γ (°)90, 95.547 (15), 9090, 90, 90
V3)1407.0 (4)5238.4 (15)
Z416
Radiation typeCu KαCu Kα
µ (mm1)5.175.52
Crystal size (mm)0.36 × 0.08 × 0.070.36 × 0.08 × 0.07
Data collection
DiffractometerEnraf Nonius CAD-4
diffractometer
Enraf Nonius CAD-4
diffractometer
Absorption correctionNumerical
(DeTitta, 1985)
Numerical
(DeTitta, 1985)
Tmin, Tmax0.370, 0.7260.361, 0.737
No. of measured, independent and
observed [I > 2σ(I)] reflections
5288, 2906, 2820 5592, 2669, 2552
Rint0.0330.038
(sin θ/λ)max1)0.6260.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.075, 2.39 0.074, 0.143, 5.84
No. of reflections29062669
No. of parameters237166
No. of restraints07
H-atom treatmentAll H-atom parameters refinedH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.44, 0.861.19, 1.13
Absolute structure?Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter?0.01 (5)

Computer programs: Enraf-Nonius XPRESS, DREADD (Blessing, 1987), SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).

Selected geometric parameters (Å, º) for (TOL) top
Se—O121.7331 (16)S—O211.4546 (14)
Se—O111.7350 (14)S—O221.4885 (14)
Se—C111.9173 (19)S—C211.7668 (19)
S—O231.4477 (15)
O12—Se—O1198.46 (8)O21—S—O22109.94 (8)
O12—Se—C1193.76 (8)O23—S—C21107.08 (9)
O11—Se—C1194.81 (8)O21—S—C21107.12 (9)
C12—C11—Se118.74 (15)O22—S—C21105.31 (8)
C16—C11—Se118.82 (15)C22—C21—S119.79 (15)
O23—S—O21114.65 (9)C26—C21—S119.76 (15)
O23—S—O22112.15 (9)
O12—Se—C11—C1252.97 (17)O21—S—C21—C22149.03 (16)
O11—Se—C11—C12151.80 (16)O22—S—C21—C2293.96 (17)
Se—C11—C12—C13176.58 (16)S—C21—C22—C23178.60 (17)
O23—S—C21—C2225.57 (19)
Hydrogen-bond geometry (Å, º) for (TOL) top
D—H···AD—HH···AD···AD—H···A
O11—H110···O22i0.83 (3)1.81 (3)2.633 (2)172 (3)
O12—H120···O22ii0.68 (3)1.99 (3)2.628 (2)157 (4)
C27—H27B···O11iii0.84 (4)2.52 (4)3.337 (3)164 (4)
Symmetry codes: (i) x+3, y+1, z+2; (ii) x+4, y+1, z+2; (iii) x+1, y+1/2, z+1/2.
Selected geometric parameters (Å, º) for (BEN) top
Se—O111.727 (7)S—O21A1.443 (6)
Se—O121.730 (6)S—O21B1.447 (6)
Se—C111.922 (7)S—O22B1.465 (6)
C11—C121.368 (13)S—O23A1.466 (6)
C11—C161.376 (11)S—C211.769 (7)
C12—C131.376 (11)C21—C221.383 (11)
C13—C141.384 (14)C21—C261.412 (12)
C14—C151.405 (11)C22—C231.380 (9)
C15—C161.366 (10)C23—C241.384 (12)
S—O22A1.424 (6)C24—C251.394 (13)
S—O23B1.434 (6)C25—C261.372 (11)
O11—Se—O1299.3 (3)O21B—S—O22B120.7 (8)
O11—Se—C1194.8 (3)O22A—S—O23A96.9 (8)
O12—Se—C1196.2 (3)O23B—S—O23A30.1 (6)
C12—C11—C16121.8 (7)O21A—S—O23A109.7 (7)
C12—C11—Se120.5 (6)O21B—S—O23A89.1 (8)
C16—C11—Se117.6 (6)O22B—S—O23A136.6 (8)
C11—C12—C13120.2 (9)O22A—S—C21116.2 (5)
C12—C13—C14118.7 (10)O23B—S—C21108.4 (7)
C13—C14—C15120.5 (8)O21A—S—C21109.8 (6)
C16—C15—C14119.8 (8)O21B—S—C21103.4 (6)
C15—C16—C11119.0 (8)O22B—S—C21100.8 (6)
O22A—S—O23B67.5 (8)O23A—S—C21101.7 (6)
O22A—S—O21A119.8 (7)C22—C21—C26121.3 (7)
O23B—S—O21A129.6 (8)C22—C21—S121.2 (6)
O22A—S—O21B137.5 (8)C26—C21—S117.5 (6)
O23B—S—O21B114.9 (8)C23—C22—C21119.2 (8)
O21A—S—O21B24.1 (7)C22—C23—C24120.4 (8)
O22A—S—O22B39.7 (7)C23—C24—C25119.9 (7)
O23B—S—O22B107.0 (7)C26—C25—C24120.9 (8)
O21A—S—O22B96.7 (7)C25—C26—C21118.2 (8)
O11—Se—C11—C12126.6 (6)O23A—S—C21—C2236.8 (8)
O12—Se—C11—C1226.7 (6)O21B—S—C21—C22128.7 (8)
Se—C11—C12—C13175.8 (6)O22B—S—C21—C22105.8 (8)
Se—C11—C16—C15175.7 (6)O23B—S—C21—C226.4 (9)
O21A—S—C21—C22153.0 (8)S—C21—C22—C23178.6 (6)
O22A—S—C21—C2267.0 (10)
 

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