3-(4-Meth-oxy-phen-yl)-1,3-selenazolo[2,3-b][1,3]benzo-thia-zol-4-ium hydrogen sulfate.

The title compound, C16H12NOSSe(+)·HSO4 (-), was obtained from a mixture of 3-(4-meth-oxy-phen-yl)[1,3]selenazolo[2,3-b][1,3]benzo-thia-zol-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 inter-molecular 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 ▶); 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

Crystal data

C16H12NOSSe+·n class="CellLine">HO4S−

M = 442.35

Monoclinic,

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 ▶) T min = 0.505, T max = 0.949

8638 measured reflections

4145 independent reflections

3555 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 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 ▶), 2075 Friedel pairs

Flack parameter: 0.038 (9)

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

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813009288/cv5401sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009288/cv5401Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009288/cv5401Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H12NOSSe+·HO4S−	F(000) = 444
Mr = 442.35	Dx = 1.840 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2780 reflections
a = 4.6408 (8) Å	θ = 2.2–28.3°
b = 18.263 (3) Å	µ = 2.64 mm−1
c = 9.4482 (16) Å	T = 100 K
β = 94.294 (3)°	Plate, colourless
V = 798.6 (2) Å3	0.30 × 0.18 × 0.02 mm
Z = 2

Bruker SMART 1K CCD diffractometer	4145 independent reflections
Radiation source: fine-focus sealed tube	3555 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
φ and ω scans	θmax = 29.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −6→6
Tmin = 0.505, Tmax = 0.949	k = −24→24
8638 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	H-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 reflections	Δρmax = 0.74 e Å−3
227 parameters	Δρmin = −0.99 e Å−3
1 restraint	Absolute structure: Flack (1983), 2075 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.038 (9)

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
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	−0.4181	0.6389	0.3898	0.021*
C3	−0.1125 (9)	0.5955 (2)	0.5288 (4)	0.0165 (8)
N4	0.0200 (7)	0.61551 (17)	0.6630 (4)	0.0147 (7)
C4A	0.2352 (8)	0.5819 (2)	0.7546 (4)	0.0149 (8)
C5	0.3787 (8)	0.5164 (2)	0.7368 (4)	0.0168 (8)
H5	0.3330	0.4866	0.6559	0.020*
C6	0.5907 (9)	0.4956 (2)	0.8401 (4)	0.0186 (9)
H6	0.6911	0.4508	0.8296	0.022*
C7	0.6596 (9)	0.5392 (2)	0.9593 (4)	0.0182 (8)
H7	0.8068	0.5238	1.0282	0.022*
C8	0.5155 (9)	0.6048 (2)	0.9785 (5)	0.0180 (8)
H8	0.5608	0.6346	1.0596	0.022*
C8A	0.3030 (8)	0.6250 (2)	0.8747 (4)	0.0146 (8)
S9	0.0967 (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)
C11	0.1148 (8)	0.5411 (2)	0.3255 (4)	0.0172 (8)
H11	0.1567	0.5896	0.2972	0.021*
C12	0.1981 (9)	0.4824 (2)	0.2441 (4)	0.0182 (8)
H12	0.3004	0.4908	0.1622	0.022*
C13	0.1307 (8)	0.4114 (2)	0.2833 (4)	0.0156 (8)
C14	−0.0266 (9)	0.3998 (2)	0.4026 (5)	0.0205 (9)
H14	−0.0819	0.3516	0.4270	0.025*
C15	−0.1006 (8)	0.4583 (2)	0.4841 (4)	0.0192 (9)
H15	−0.2019	0.4498	0.5663	0.023*
O1	0.2001 (6)	0.35027 (15)	0.2094 (3)	0.0199 (6)
C16	0.3593 (9)	0.3608 (2)	0.0861 (4)	0.0198 (9)
H16A	0.3901	0.3134	0.0411	0.030*
H16B	0.5466	0.3833	0.1145	0.030*
H16C	0.2497	0.3930	0.0188	0.030*
S1	0.2806 (2)	0.78392 (5)	0.26484 (11)	0.0180 (2)
O2	0.3759 (7)	0.7346 (2)	0.1596 (3)	0.0333 (8)
O3	0.2090 (6)	0.74833 (15)	0.3937 (3)	0.0228 (6)
O4	0.0395 (6)	0.83188 (17)	0.2081 (3)	0.0256 (7)
O5	0.5298 (6)	0.83793 (17)	0.3069 (4)	0.0277 (7)
H5O	0.6634	0.8370	0.2413	0.042*

	U11	U22	U33	U12	U13	U23
Se1	0.01455 (16)	0.01458 (16)	0.02001 (18)	0.00098 (18)	0.00359 (13)	0.00010 (19)
C2	0.0167 (19)	0.018 (2)	0.018 (2)	−0.0019 (16)	0.0052 (16)	0.0018 (16)
C3	0.0159 (19)	0.0149 (18)	0.019 (2)	−0.0012 (15)	0.0058 (16)	0.0005 (16)
N4	0.0130 (15)	0.0124 (15)	0.0192 (17)	−0.0010 (13)	0.0049 (13)	−0.0009 (13)
C4A	0.0115 (18)	0.0145 (18)	0.019 (2)	−0.0025 (15)	0.0036 (15)	−0.0001 (15)
C5	0.017 (2)	0.0164 (19)	0.018 (2)	−0.0027 (16)	0.0047 (16)	−0.0004 (16)
C6	0.0153 (19)	0.0165 (19)	0.025 (2)	0.0015 (16)	0.0085 (17)	0.0024 (17)
C7	0.0135 (19)	0.022 (2)	0.019 (2)	0.0007 (16)	0.0020 (16)	0.0031 (17)
C8	0.016 (2)	0.0172 (19)	0.021 (2)	−0.0006 (16)	0.0050 (17)	0.0012 (17)
C8A	0.0156 (19)	0.0124 (18)	0.016 (2)	0.0009 (15)	0.0053 (15)	−0.0010 (15)
S9	0.0163 (4)	0.0168 (5)	0.0192 (5)	0.0003 (3)	0.0028 (4)	−0.0013 (4)
C9A	0.0155 (19)	0.0165 (18)	0.0175 (19)	−0.0055 (16)	0.0054 (15)	−0.0042 (16)
C10	0.0132 (18)	0.0137 (18)	0.021 (2)	−0.0009 (15)	0.0019 (16)	−0.0011 (16)
C11	0.0149 (19)	0.0165 (19)	0.020 (2)	−0.0005 (16)	0.0007 (16)	0.0008 (16)
C12	0.018 (2)	0.019 (2)	0.018 (2)	−0.0002 (16)	0.0034 (16)	0.0003 (16)
C13	0.0148 (19)	0.0155 (19)	0.016 (2)	0.0012 (15)	0.0000 (15)	−0.0035 (16)
C14	0.019 (2)	0.018 (2)	0.025 (2)	−0.0031 (17)	0.0067 (17)	0.0013 (17)
C15	0.0171 (19)	0.021 (2)	0.021 (2)	−0.0022 (16)	0.0055 (17)	−0.0016 (17)
O1	0.0223 (15)	0.0163 (14)	0.0223 (15)	−0.0003 (12)	0.0096 (13)	−0.0003 (12)
C16	0.021 (2)	0.021 (2)	0.018 (2)	−0.0003 (17)	0.0067 (17)	−0.0029 (17)
S1	0.0164 (5)	0.0182 (5)	0.0197 (5)	0.0014 (4)	0.0029 (4)	0.0002 (4)
O2	0.0372 (17)	0.036 (2)	0.0270 (14)	0.0050 (17)	0.0053 (13)	−0.0125 (16)
O3	0.0204 (15)	0.0232 (15)	0.0252 (15)	0.0021 (12)	0.0041 (12)	0.0073 (12)
O4	0.0152 (15)	0.0258 (16)	0.0353 (18)	0.0019 (12)	−0.0007 (13)	0.0102 (14)
O5	0.0167 (15)	0.0263 (17)	0.0406 (18)	−0.0014 (13)	0.0064 (14)	−0.0019 (15)

Se1—C9A	1.834 (4)	C10—C15	1.394 (5)
Se1—C2	1.859 (4)	C10—C11	1.399 (6)
C2—C3	1.345 (5)	C11—C12	1.391 (6)
C2—H2	0.9500	C11—H11	0.9500
C3—N4	1.415 (5)	C12—C13	1.390 (6)
C3—C10	1.485 (5)	C12—H12	0.9500
N4—C9A	1.373 (5)	C13—O1	1.367 (5)
N4—C4A	1.412 (5)	C13—C14	1.404 (6)
C4A—C5	1.385 (5)	C14—C15	1.376 (6)
C4A—C8A	1.397 (5)	C14—H14	0.9500
C5—C6	1.386 (6)	C15—H15	0.9500
C5—H5	0.9500	O1—C16	1.439 (5)
C6—C7	1.397 (6)	C16—H16A	0.9800
C6—H6	0.9500	C16—H16B	0.9800
C7—C8	1.391 (6)	C16—H16C	0.9800
C7—H7	0.9500	S1—O2	1.436 (3)
C8—C8A	1.388 (6)	S1—O3	1.441 (3)
C8—H8	0.9500	S1—O4	1.489 (3)
C8A—S9	1.759 (4)	S1—O5	1.549 (3)
S9—C9A	1.710 (4)	O5—H5O	0.9086
C9A—Se1—C2	84.92 (18)	C15—C10—C11	118.3 (4)
C3—C2—Se1	114.8 (3)	C15—C10—C3	123.9 (4)
C3—C2—H2	122.6	C11—C10—C3	117.7 (3)
Se1—C2—H2	122.6	C12—C11—C10	121.1 (4)
C2—C3—N4	112.5 (4)	C12—C11—H11	119.5
C2—C3—C10	123.7 (4)	C10—C11—H11	119.5
N4—C3—C10	123.7 (3)	C11—C12—C13	119.6 (4)
C9A—N4—C4A	113.2 (3)	C11—C12—H12	120.2
C9A—N4—C3	114.2 (3)	C13—C12—H12	120.2
C4A—N4—C3	132.6 (3)	O1—C13—C12	124.0 (4)
C5—C4A—C8A	120.3 (4)	O1—C13—C14	116.3 (4)
C5—C4A—N4	128.7 (4)	C12—C13—C14	119.7 (4)
C8A—C4A—N4	111.0 (3)	C15—C14—C13	119.9 (4)
C4A—C5—C6	118.3 (4)	C15—C14—H14	120.0
C4A—C5—H5	120.9	C13—C14—H14	120.0
C6—C5—H5	120.9	C14—C15—C10	121.3 (4)
C5—C6—C7	121.3 (4)	C14—C15—H15	119.4
C5—C6—H6	119.4	C10—C15—H15	119.4
C7—C6—H6	119.4	C13—O1—C16	117.3 (3)
C8—C7—C6	120.9 (4)	O1—C16—H16A	109.5
C8—C7—H7	119.6	O1—C16—H16B	109.5
C6—C7—H7	119.6	H16A—C16—H16B	109.5
C8A—C8—C7	117.4 (4)	O1—C16—H16C	109.5
C8A—C8—H8	121.3	H16A—C16—H16C	109.5
C7—C8—H8	121.3	H16B—C16—H16C	109.5
C8—C8A—C4A	121.9 (4)	O2—S1—O3	113.9 (2)
C8—C8A—S9	125.9 (3)	O2—S1—O4	112.44 (19)
C4A—C8A—S9	112.2 (3)	O3—S1—O4	110.80 (18)
C9A—S9—C8A	90.01 (19)	O2—S1—O5	108.31 (19)
N4—C9A—S9	113.6 (3)	O3—S1—O5	106.59 (18)
N4—C9A—Se1	113.5 (3)	O4—S1—O5	104.13 (18)
S9—C9A—Se1	132.9 (2)	S1—O5—H5O	110.3
C9A—Se1—C2—C3	0.2 (3)	C4A—N4—C9A—S9	0.3 (4)
Se1—C2—C3—N4	0.6 (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—Se1	1.5 (4)
C10—C3—N4—C9A	174.9 (4)	C8A—S9—C9A—N4	0.1 (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—S9	178.8 (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—C15	74.1 (5)
C3—N4—C4A—C8A	177.6 (4)	C2—C3—C10—C11	66.4 (5)
C8A—C4A—C5—C6	−0.5 (6)	N4—C3—C10—C11	−109.4 (4)
N4—C4A—C5—C6	177.9 (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—C8	0.4 (6)	C10—C11—C12—C13	1.6 (6)
C6—C7—C8—C8A	−0.2 (6)	C11—C12—C13—O1	179.2 (4)
C7—C8—C8A—C4A	−0.3 (6)	C11—C12—C13—C14	1.5 (6)
C7—C8—C8A—S9	−178.7 (3)	O1—C13—C14—C15	178.9 (4)
C5—C4A—C8A—C8	0.7 (6)	C12—C13—C14—C15	−3.3 (6)
N4—C4A—C8A—C8	−177.9 (4)	C13—C14—C15—C10	1.9 (6)
C5—C4A—C8A—S9	179.3 (3)	C11—C10—C15—C14	1.2 (6)
N4—C4A—C8A—S9	0.7 (4)	C3—C10—C15—C14	177.7 (4)
C8—C8A—S9—C9A	178.1 (4)	C12—C13—O1—C16	1.7 (5)
C4A—C8A—S9—C9A	−0.4 (3)	C14—C13—O1—C16	179.5 (3)

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

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) ; (ii) ; (iii) .