Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 5| May 2013| Pages o703-o704
https://doi.org/10.1107/S1600536813009288

3-(4-Meth­­oxy­phen­yl)-1,3-selenazolo[2,3-b][1,3]benzo­thia­zol-4-ium hydrogen sulfate

Gunay Z. Mammadova,a* Zhanna V. Matsulevich,b Galina N. Borisova,b Alexander V. Borisovb and Victor N. Khrustalevc

aBaku State University, Z. Khalilov St 23, Baku, AZ-1148, Azerbaijan, bR.E. Alekseev Nizhny Novgorod State Technical University, 24 Minin St, Nizhny Novgorod, 603950, Russian Federation, and cX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St, B-334, Moscow 119991, Russian Federation
*Correspondence e-mail: gunka479@mail.ru

(Received 2 April 2013; accepted 5 April 2013; online 13 April 2013)

The title compound, C16H12NOSSe+·HSO4−, was obtained from a mixture of 3-(4-meth­oxy­phen­yl)[1,3]selenazolo[2,3-b][1,3]benzo­thia­zol-4-ium chloride and potassium hydrogen sulfate. In the cation, the benzene ring is twisted by 71.62 (7)° from the tricycle mean plane. In the crystal, O—H⋯O hydrogen bonds link the anions into chains along [100]. The anions in adjacent chains are linked via weak C—H⋯O hydrogen bonds. The crystal packing exhibits short inter­molecular contacts between the chalcogen unit and the O atoms: Se⋯O(anion) 2.713 (3), Se⋯O(cation) 2.987 (3) and S⋯O(anion) 2.958 (3) Å.

Related literature

For details of the synthesis and the biological properties of selenium- and nitro­gen-containing heterocycles, see: Back (2009[Back, T. G. (2009). Can. J. Chem. 87, 1657-1674.]); Mlochowski & Giurg (2009[Mlochowski, J. & Giurg, M. (2009). In Topics in Heterocyclic Chemistry, edited by R. R. Gupta, Vol. 19, pp. 287-340. Berlin, Heidelberg: Springer-Verlag.]); Mukherjee et al. (2010[Mukherjee, A. J., Zade, S. S., Singh, H. B. & Sunoj, R. B. (2010). Chem. Rev. 110, 4357-4416.]); Selvakumar et al. (2010[Selvakumar, K., Singh, H. B. & Butcher, R. J. (2010). Chem. Eur. J. 16, 10576-10591.]). For the synthesis of the starting compound, 3-(4-meth­oxy­phen­yl)[1,3]selenazolo[2,3-b][1,3]benzo­thia­zol-4-ium chloride, see: Borisov et al. (2012[Borisov, A. V., Matsulevich, Zh. V., Osmanov, V. K. & Borisova, G. N. (2012). Chem. Heterocycl. Compd, 48, 1428-1429.]).

[Scheme 1]

Experimental

Crystal data

  • C16H12NOSSe+·HO4S−

  • Mr = 442.35

  • Monoclinic, P 21

  • a = 4.6408 (8) Å

  • b = 18.263 (3) Å

  • c = 9.4482 (16) Å

  • β = 94.294 (3)°

  • V = 798.6 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.64 mm−1

  • T = 100 K

  • 0.30 × 0.18 × 0.02 mm
Data collection

  • Bruker SMART 1K CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1998[Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.505, Tmax = 0.949

  • 8638 measured reflections

  • 4145 independent reflections

  • 3555 reflections with I > 2σ(I)

  • Rint = 0.052
Refinement

  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.085

  • S = 0.97

  • 4145 reflections

  • 227 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.74 e Å−3

  • Δρmin = −0.99 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2075 Friedel pairs

  • Flack parameter: 0.038 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O5—H5O⋯O4i 0.91 1.80 2.610 (4) 147
C6—H6⋯O4ii 0.95 2.54 3.494 (5) 178
C8—H8⋯O2iii 0.95 2.26 3.022 (5) 137
Symmetry codes: (i) x+1, y, z; (ii) [-x+1, y-{\script{1\over 2}}, -z+1]; (iii) x, y, z+1.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813009288/cv5401sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813009288/cv5401Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813009288/cv5401Isup3.cml

checkCIF report


Comment top

In the last years, the selenium- and nitrogen-containing heterocycles have attracted considerable attention owing to the variety of their pharmacological properties (Back, 2009; Mlochowski & Giurg, 2009; Mukherjee et al., 2010; Selvakumar et al., 2010). This article describes the structure of 3-(4-methoxyphenyl)[1,3]selenazolo[2,3-b][1,3]benzothiazol-4-ium hydrogen sulfate, [C16H12NOSSe]+.[HSO4]-, (I), which was obtained by the reaction of 3-(4-methoxyphenyl)[1,3]selenazolo[2,3-b][1,3]benzothiazol-4-ium chloride (Borisov et al., 2012) with potassium hydrogen sulfate (Figure 1).

The compound I is a salt consisting of 3-(4-methoxyphenyl)[1,3]selenazolo[2,3-b][1,3]benzothiazol-4-ium cation and hydrogen sulfate anion (Figure 2). The cation of I comprises a fused tricyclic system containing two five-membered rings (1,3-selenazole and 1,3-thiazole) and one six-membered ring (benzene). The tricyclic system is practically planar (r.m.s deviation = 0.020 Å). The methoxy group is almost coplanar to the plane of the phenyl substituent (the C12—C13—O1—C16 torsion angle is 1.7 (5)°). The dihedral angle between the mean planes of the tricyclic system and methoxyphenyl fragment is 71.82 (6)°.

In the crystal, anions form chains along the a axis through the intermolecular O—H···O hydrogen bonding interactions (Table 1, Figure 3). Weak intermolecular C—H···O hydrogen bonds (Table 1, Figure 3) as well as non-valent attractive Se···O (Se1···O3b 2.713 (3), Se1···O1c 2.987 (3), Se1···O3 3.366 (3), Se1···O5b 3.423 (3) Å) and S···O [S9···O2a 2.958 (3) and S9···O1c 3.050 (3) Å] interactions consolidate further the three-dimensional-crystal packing (Figure 3) [symmetry codes: (a) x, y, z + 1; (b) x–1, y, z; (c) –x, y + 0.5, –z + 1].

Related literature top

For details of the synthesis and the biological properties of selenium- and nitrogen-containing heterocycles, see: Back (2009); Mlochowski & Giurg (2009); Mukherjee et al. (2010); Selvakumar et al. (2010). For the synthesis of the starting compound, 3-(4-methoxyphenyl)[1,3]selenazolo[2,3-b][1,3]benzothiazol-4-ium chloride, see: Borisov et al. (2012).

Experimental top

A mixture of 3-(4-methoxyphenyl)[1,3]selenazolo[2,3-b][1,3]benzothiazol-4-ium chloride (0.19 g, 0.5 mmol) with KHSO4 (0.072 g, 0.53 mmol) in CH3OH (20 ml) was refluxed for 0.5 h to dissolve the starting materials. After that the reaction mixture was concentrated in vacuo. Then CH2Cl2 (20 ml) was added to the solid to give precipitate of KCl, which was separated by filtration. The filtrate was concentrated in vacuo. The solid was re-crystallized from CH2Cl2 to give I as colorless crystals. Yield is 93%. M.p. = 510–512 K. 1H NMR (DMSO-d6, 600 MHz, 302 K): δ = 8.42 (1H, d, J = 8.0, H8), 8.23 (1H, s, H2), 7.63 (1H, t, J = 8.0, H7), 7.59 (2H, d, J = 8.8, H11, H15), 7.48 (1H, t, J = 8.0, H6), 7.25 (2H, d, J = 8.8, H12, H14), 6.81 (1H, d, J = 8.1, H5), 3.87 (3H, s, OMe). Anal. Calcd. for C16H13NO5S2Se: C, 43.45; H, 2.96; N, 3.17. Found: C, 43.37; H, 2.93; N, 3.12.

Refinement top

The hydroxyl hydrogen atom was localized in the difference-Fourier map and included in the refinement with fixed positional and isotropic displacement parameters [Uiso(H) = 1.5Ueq(O)]. The other hydrogen atoms were placed in calculated positions with C—H = 0.95 Å (CH) and 0.98 Å (CH3) and refined in the riding model with fixed isotropic displacement parameters [Uiso(H) = 1.5Ueq(C) for the CH3 group and 1.2Ueq(C) for the CH groups].

Structure description top

In the last years, the selenium- and nitrogen-containing heterocycles have attracted considerable attention owing to the variety of their pharmacological properties (Back, 2009; Mlochowski & Giurg, 2009; Mukherjee et al., 2010; Selvakumar et al., 2010). This article describes the structure of 3-(4-methoxyphenyl)[1,3]selenazolo[2,3-b][1,3]benzothiazol-4-ium hydrogen sulfate, [C16H12NOSSe]+.[HSO4]-, (I), which was obtained by the reaction of 3-(4-methoxyphenyl)[1,3]selenazolo[2,3-b][1,3]benzothiazol-4-ium chloride (Borisov et al., 2012) with potassium hydrogen sulfate (Figure 1).

The compound I is a salt consisting of 3-(4-methoxyphenyl)[1,3]selenazolo[2,3-b][1,3]benzothiazol-4-ium cation and hydrogen sulfate anion (Figure 2). The cation of I comprises a fused tricyclic system containing two five-membered rings (1,3-selenazole and 1,3-thiazole) and one six-membered ring (benzene). The tricyclic system is practically planar (r.m.s deviation = 0.020 Å). The methoxy group is almost coplanar to the plane of the phenyl substituent (the C12—C13—O1—C16 torsion angle is 1.7 (5)°). The dihedral angle between the mean planes of the tricyclic system and methoxyphenyl fragment is 71.82 (6)°.

In the crystal, anions form chains along the a axis through the intermolecular O—H···O hydrogen bonding interactions (Table 1, Figure 3). Weak intermolecular C—H···O hydrogen bonds (Table 1, Figure 3) as well as non-valent attractive Se···O (Se1···O3b 2.713 (3), Se1···O1c 2.987 (3), Se1···O3 3.366 (3), Se1···O5b 3.423 (3) Å) and S···O [S9···O2a 2.958 (3) and S9···O1c 3.050 (3) Å] interactions consolidate further the three-dimensional-crystal packing (Figure 3) [symmetry codes: (a) x, y, z + 1; (b) x–1, y, z; (c) –x, y + 0.5, –z + 1].

For details of the synthesis and the biological properties of selenium- and nitrogen-containing heterocycles, see: Back (2009); Mlochowski & Giurg (2009); Mukherjee et al. (2010); Selvakumar et al. (2010). For the synthesis of the starting compound, 3-(4-methoxyphenyl)[1,3]selenazolo[2,3-b][1,3]benzothiazol-4-ium chloride, see: Borisov et al. (2012).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Reaction of 3-(4-methoxyphenyl)[1,3]selenazolo[2,3-b][1,3]benzothiazol-4-ium chloride with potassium hydrogen sulfate.
[Figure 2] Fig. 2. Molecular structure of I. Displacement ellipsoids are shown at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
[Figure 3] Fig. 3. A portion of crystal packing of I viewed approximately down the a axis. Dashed lines indicate the intermolecular O—H···O and C—H···O hydrogen bonds as well as the non-valent Se···O and S···O attractive interactions.
3-(4-Methoxyphenyl)-1,3-selenazolo[2,3-b][1,3]benzothiazol-4-ium hydrogen sulfate top
Crystal data top
C16H12NOSSe+·HO4S−F(000) = 444
Mr = 442.35Dx = 1.840 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2780 reflections
a = 4.6408 (8) Åθ = 2.2–28.3°
b = 18.263 (3) ŵ = 2.64 mm−1
c = 9.4482 (16) ÅT = 100 K
β = 94.294 (3)°Plate, colourless
V = 798.6 (2) Å30.30 × 0.18 × 0.02 mm
Z = 2
Data collection top
Bruker SMART 1K CCD
diffractometer		4145 independent reflections
Radiation source: fine-focus sealed tube3555 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
φ and ω scansθmax = 29.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)		h = −6→6
Tmin = 0.505, Tmax = 0.949k = −24→24
8638 measured reflectionsl = −12→12
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.001P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
4145 reflectionsΔρmax = 0.74 e Å−3
227 parametersΔρmin = −0.99 e Å−3
1 restraintAbsolute structure: Flack (1983), 2075 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.038 (9)
Crystal data top
C16H12NOSSe+·HO4S−V = 798.6 (2) Å3
Mr = 442.35Z = 2
Monoclinic, P21Mo Kα radiation
a = 4.6408 (8) ŵ = 2.64 mm−1
b = 18.263 (3) ÅT = 100 K
c = 9.4482 (16) Å0.30 × 0.18 × 0.02 mm
β = 94.294 (3)°
Data collection top
Bruker SMART 1K CCD
diffractometer		4145 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)		3555 reflections with I > 2σ(I)
Tmin = 0.505, Tmax = 0.949Rint = 0.052
8638 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.085Δρmax = 0.74 e Å−3
S = 0.97Δρmin = −0.99 e Å−3
4145 reflectionsAbsolute structure: Flack (1983), 2075 Friedel pairs
227 parametersAbsolute structure parameter: 0.038 (9)
1 restraint
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
Se1−0.35253 (8)0.72534 (2)0.59512 (4)0.01626 (9)
C2−0.3094 (9)0.6448 (2)0.4783 (4)0.0173 (8)
H2−0.41810.63890.38980.021*
C3−0.1125 (9)0.5955 (2)0.5288 (4)0.0165 (8)
N40.0200 (7)0.61551 (17)0.6630 (4)0.0147 (7)
C4A0.2352 (8)0.5819 (2)0.7546 (4)0.0149 (8)
C50.3787 (8)0.5164 (2)0.7368 (4)0.0168 (8)
H50.33300.48660.65590.020*
C60.5907 (9)0.4956 (2)0.8401 (4)0.0186 (9)
H60.69110.45080.82960.022*
C70.6596 (9)0.5392 (2)0.9593 (4)0.0182 (8)
H70.80680.52381.02820.022*
C80.5155 (9)0.6048 (2)0.9785 (5)0.0180 (8)
H80.56080.63461.05960.022*
C8A0.3030 (8)0.6250 (2)0.8747 (4)0.0146 (8)
S90.0967 (2)0.70586 (5)0.87325 (11)0.0174 (2)
C9A−0.0728 (8)0.6813 (2)0.7133 (4)0.0163 (8)
C10−0.0297 (8)0.5298 (2)0.4485 (4)0.0158 (8)
C110.1148 (8)0.5411 (2)0.3255 (4)0.0172 (8)
H110.15670.58960.29720.021*
C120.1981 (9)0.4824 (2)0.2441 (4)0.0182 (8)
H120.30040.49080.16220.022*
C130.1307 (8)0.4114 (2)0.2833 (4)0.0156 (8)
C14−0.0266 (9)0.3998 (2)0.4026 (5)0.0205 (9)
H14−0.08190.35160.42700.025*
C15−0.1006 (8)0.4583 (2)0.4841 (4)0.0192 (9)
H15−0.20190.44980.56630.023*
O10.2001 (6)0.35027 (15)0.2094 (3)0.0199 (6)
C160.3593 (9)0.3608 (2)0.0861 (4)0.0198 (9)
H16A0.39010.31340.04110.030*
H16B0.54660.38330.11450.030*
H16C0.24970.39300.01880.030*
S10.2806 (2)0.78392 (5)0.26484 (11)0.0180 (2)
O20.3759 (7)0.7346 (2)0.1596 (3)0.0333 (8)
O30.2090 (6)0.74833 (15)0.3937 (3)0.0228 (6)
O40.0395 (6)0.83188 (17)0.2081 (3)0.0256 (7)
O50.5298 (6)0.83793 (17)0.3069 (4)0.0277 (7)
H5O0.66340.83700.24130.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se10.01455 (16)0.01458 (16)0.02001 (18)0.00098 (18)0.00359 (13)0.00010 (19)
C20.0167 (19)0.018 (2)0.018 (2)−0.0019 (16)0.0052 (16)0.0018 (16)
C30.0159 (19)0.0149 (18)0.019 (2)−0.0012 (15)0.0058 (16)0.0005 (16)
N40.0130 (15)0.0124 (15)0.0192 (17)−0.0010 (13)0.0049 (13)−0.0009 (13)
C4A0.0115 (18)0.0145 (18)0.019 (2)−0.0025 (15)0.0036 (15)−0.0001 (15)
C50.017 (2)0.0164 (19)0.018 (2)−0.0027 (16)0.0047 (16)−0.0004 (16)
C60.0153 (19)0.0165 (19)0.025 (2)0.0015 (16)0.0085 (17)0.0024 (17)
C70.0135 (19)0.022 (2)0.019 (2)0.0007 (16)0.0020 (16)0.0031 (17)
C80.016 (2)0.0172 (19)0.021 (2)−0.0006 (16)0.0050 (17)0.0012 (17)
C8A0.0156 (19)0.0124 (18)0.016 (2)0.0009 (15)0.0053 (15)−0.0010 (15)
S90.0163 (4)0.0168 (5)0.0192 (5)0.0003 (3)0.0028 (4)−0.0013 (4)
C9A0.0155 (19)0.0165 (18)0.0175 (19)−0.0055 (16)0.0054 (15)−0.0042 (16)
C100.0132 (18)0.0137 (18)0.021 (2)−0.0009 (15)0.0019 (16)−0.0011 (16)
C110.0149 (19)0.0165 (19)0.020 (2)−0.0005 (16)0.0007 (16)0.0008 (16)
C120.018 (2)0.019 (2)0.018 (2)−0.0002 (16)0.0034 (16)0.0003 (16)
C130.0148 (19)0.0155 (19)0.016 (2)0.0012 (15)0.0000 (15)−0.0035 (16)
C140.019 (2)0.018 (2)0.025 (2)−0.0031 (17)0.0067 (17)0.0013 (17)
C150.0171 (19)0.021 (2)0.021 (2)−0.0022 (16)0.0055 (17)−0.0016 (17)
O10.0223 (15)0.0163 (14)0.0223 (15)−0.0003 (12)0.0096 (13)−0.0003 (12)
C160.021 (2)0.021 (2)0.018 (2)−0.0003 (17)0.0067 (17)−0.0029 (17)
S10.0164 (5)0.0182 (5)0.0197 (5)0.0014 (4)0.0029 (4)0.0002 (4)
O20.0372 (17)0.036 (2)0.0270 (14)0.0050 (17)0.0053 (13)−0.0125 (16)
O30.0204 (15)0.0232 (15)0.0252 (15)0.0021 (12)0.0041 (12)0.0073 (12)
O40.0152 (15)0.0258 (16)0.0353 (18)0.0019 (12)−0.0007 (13)0.0102 (14)
O50.0167 (15)0.0263 (17)0.0406 (18)−0.0014 (13)0.0064 (14)−0.0019 (15)
Geometric parameters (Å, º) top
Se1—C9A1.834 (4)C10—C151.394 (5)
Se1—C21.859 (4)C10—C111.399 (6)
C2—C31.345 (5)C11—C121.391 (6)
C2—H20.9500C11—H110.9500
C3—N41.415 (5)C12—C131.390 (6)
C3—C101.485 (5)C12—H120.9500
N4—C9A1.373 (5)C13—O11.367 (5)
N4—C4A1.412 (5)C13—C141.404 (6)
C4A—C51.385 (5)C14—C151.376 (6)
C4A—C8A1.397 (5)C14—H140.9500
C5—C61.386 (6)C15—H150.9500
C5—H50.9500O1—C161.439 (5)
C6—C71.397 (6)C16—H16A0.9800
C6—H60.9500C16—H16B0.9800
C7—C81.391 (6)C16—H16C0.9800
C7—H70.9500S1—O21.436 (3)
C8—C8A1.388 (6)S1—O31.441 (3)
C8—H80.9500S1—O41.489 (3)
C8A—S91.759 (4)S1—O51.549 (3)
S9—C9A1.710 (4)O5—H5O0.9086
C9A—Se1—C284.92 (18)C15—C10—C11118.3 (4)
C3—C2—Se1114.8 (3)C15—C10—C3123.9 (4)
C3—C2—H2122.6C11—C10—C3117.7 (3)
Se1—C2—H2122.6C12—C11—C10121.1 (4)
C2—C3—N4112.5 (4)C12—C11—H11119.5
C2—C3—C10123.7 (4)C10—C11—H11119.5
N4—C3—C10123.7 (3)C11—C12—C13119.6 (4)
C9A—N4—C4A113.2 (3)C11—C12—H12120.2
C9A—N4—C3114.2 (3)C13—C12—H12120.2
C4A—N4—C3132.6 (3)O1—C13—C12124.0 (4)
C5—C4A—C8A120.3 (4)O1—C13—C14116.3 (4)
C5—C4A—N4128.7 (4)C12—C13—C14119.7 (4)
C8A—C4A—N4111.0 (3)C15—C14—C13119.9 (4)
C4A—C5—C6118.3 (4)C15—C14—H14120.0
C4A—C5—H5120.9C13—C14—H14120.0
C6—C5—H5120.9C14—C15—C10121.3 (4)
C5—C6—C7121.3 (4)C14—C15—H15119.4
C5—C6—H6119.4C10—C15—H15119.4
C7—C6—H6119.4C13—O1—C16117.3 (3)
C8—C7—C6120.9 (4)O1—C16—H16A109.5
C8—C7—H7119.6O1—C16—H16B109.5
C6—C7—H7119.6H16A—C16—H16B109.5
C8A—C8—C7117.4 (4)O1—C16—H16C109.5
C8A—C8—H8121.3H16A—C16—H16C109.5
C7—C8—H8121.3H16B—C16—H16C109.5
C8—C8A—C4A121.9 (4)O2—S1—O3113.9 (2)
C8—C8A—S9125.9 (3)O2—S1—O4112.44 (19)
C4A—C8A—S9112.2 (3)O3—S1—O4110.80 (18)
C9A—S9—C8A90.01 (19)O2—S1—O5108.31 (19)
N4—C9A—S9113.6 (3)O3—S1—O5106.59 (18)
N4—C9A—Se1113.5 (3)O4—S1—O5104.13 (18)
S9—C9A—Se1132.9 (2)S1—O5—H5O110.3
C9A—Se1—C2—C30.2 (3)C4A—N4—C9A—S90.3 (4)
Se1—C2—C3—N40.6 (4)C3—N4—C9A—S9−178.3 (3)
Se1—C2—C3—C10−175.7 (3)C4A—N4—C9A—Se1−180.0 (3)
C2—C3—N4—C9A−1.3 (5)C3—N4—C9A—Se11.5 (4)
C10—C3—N4—C9A174.9 (4)C8A—S9—C9A—N40.1 (3)
C2—C3—N4—C4A−179.5 (4)C8A—S9—C9A—Se1−179.6 (3)
C10—C3—N4—C4A−3.3 (6)C2—Se1—C9A—N4−0.9 (3)
C9A—N4—C4A—C5−179.1 (4)C2—Se1—C9A—S9178.8 (3)
C3—N4—C4A—C5−0.9 (7)C2—C3—C10—C15−110.1 (5)
C9A—N4—C4A—C8A−0.6 (4)N4—C3—C10—C1574.1 (5)
C3—N4—C4A—C8A177.6 (4)C2—C3—C10—C1166.4 (5)
C8A—C4A—C5—C6−0.5 (6)N4—C3—C10—C11−109.4 (4)
N4—C4A—C5—C6177.9 (4)C15—C10—C11—C12−2.9 (6)
C4A—C5—C6—C7−0.1 (6)C3—C10—C11—C12−179.6 (4)
C5—C6—C7—C80.4 (6)C10—C11—C12—C131.6 (6)
C6—C7—C8—C8A−0.2 (6)C11—C12—C13—O1179.2 (4)
C7—C8—C8A—C4A−0.3 (6)C11—C12—C13—C141.5 (6)
C7—C8—C8A—S9−178.7 (3)O1—C13—C14—C15178.9 (4)
C5—C4A—C8A—C80.7 (6)C12—C13—C14—C15−3.3 (6)
N4—C4A—C8A—C8−177.9 (4)C13—C14—C15—C101.9 (6)
C5—C4A—C8A—S9179.3 (3)C11—C10—C15—C141.2 (6)
N4—C4A—C8A—S90.7 (4)C3—C10—C15—C14177.7 (4)
C8—C8A—S9—C9A178.1 (4)C12—C13—O1—C161.7 (5)
C4A—C8A—S9—C9A−0.4 (3)C14—C13—O1—C16179.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5O···O4i0.911.802.610 (4)147
C6—H6···O4ii0.952.543.494 (5)178
C8—H8···O2iii0.952.263.022 (5)137
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1; (iii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC16H12NOSSe+·HO4S−
Mr442.35
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)4.6408 (8), 18.263 (3), 9.4482 (16)
β (°) 94.294 (3)
V (Å3)798.6 (2)
Z2
Radiation typeMo Kα
µ (mm−1)2.64
Crystal size (mm)0.30 × 0.18 × 0.02
Data collection
DiffractometerBruker SMART 1K CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1998)
Tmin, Tmax0.505, 0.949
No. of measured, independent and
observed [I > 2σ(I)] reflections		8638, 4145, 3555
Rint0.052
(sin θ/λ)max (Å−1)0.682
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.085, 0.97
No. of reflections4145
No. of parameters227
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.74, −0.99
Absolute structureFlack (1983), 2075 Friedel pairs
Absolute structure parameter0.038 (9)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5O···O4i0.911.802.610 (4)147
C6—H6···O4ii0.952.543.494 (5)178
C8—H8···O2iii0.952.263.022 (5)137
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1; (iii) x, y, z+1.
 

Acknowledgements

We thank Professor Abel M. Maharramov for fruitful discussions and help in this work.

References

First citationBack, T. G. (2009). Can. J. Chem. 87, 1657–1674.  Web of Science CrossRef CAS Google Scholar
 First citationBorisov, A. V., Matsulevich, Zh. V., Osmanov, V. K. & Borisova, G. N. (2012). Chem. Heterocycl. Compd, 48, 1428–1429.  Web of Science CrossRef CAS Google Scholar
 First citationBruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationMlochowski, J. & Giurg, M. (2009). In Topics in Heterocyclic Chemistry, edited by R. R. Gupta, Vol. 19, pp. 287–340. Berlin, Heidelberg: Springer-Verlag.  Google Scholar
 First citationMukherjee, A. J., Zade, S. S., Singh, H. B. & Sunoj, R. B. (2010). Chem. Rev. 110, 4357–4416.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationSelvakumar, K., Singh, H. B. & Butcher, R. J. (2010). Chem. Eur. J. 16, 10576–10591.  Web of Science CSD CrossRef CAS PubMed Google Scholar
 First citationSheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 5| May 2013| Pages o703-o704
https://doi.org/10.1107/S1600536813009288
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS