4-Chloro-selanyl-3,5-diethyl-1H-pyrazol-2-ium chloride.

In the cation of the title compound, C(7)H(12)ClN(2)Se(+)·Cl(-), the ethyl-ene groups and the Se-Cl fragment adopt a cis configuration with a C-Se-Cl angle of 96.09 (6)°. In the crystal, inter-molecular N-H⋯Cl hydrogen bonds link two cations and two chlorine anions into centrosymmetric clusters. π-π inter-actions between the pyrazole rings [centroid-centroid distance of 3.530 (2) Å] link these clusters into columns along [001] with short inter-molecular Se⋯Cl(-) contacts of 2.995 (1) Å.

Related literature

For reviews of organoselenium chemistry, see: Krief (1995 ▶); Freudendahl et al. (2009 ▶). For structural studies of bis­(1H-pyrazol-4-yl)selenides, see: Seredyuk, Fritsky et al. (2010 ▶). For structural studies of d-metal complexes of bis­(1H-pyrazol-4-yl)selenides, see: Seredyuk et al. (2007 ▶, 2009 ▶); Seredyuk, Moroz et al. (2010 ▶).

Experimental

Crystal data

C7H12ClN2Se+·Cl−

M = 274.05

Monoclinic,

a = 8.1944 (6) Å

b = 19.3719 (10) Å

c = 7.1241 (3) Å

β = 111.025 (6)°

V = 1055.60 (10) Å3

Z = 4

Mo Kα radiation

μ = 4.01 mm−1

T = 120 K

0.30 × 0.21 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (XPREP in SHELXTL; Sheldrick, 2008 ▶) T min = 0.379, T max = 0.699

13385 measured reflections

2423 independent reflections

2040 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.049

S = 1.04

2423 reflections

119 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.38 e Å−3

Data collection: COLLECT (Bruker–Nonius, 2004 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2005 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811043790/cv5179sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043790/cv5179Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811043790/cv5179Isup3.cml

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

C7H12ClN2Se+·Cl−	F(000) = 544
Mr = 274.05	Dx = 1.724 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3966 reflections
a = 8.1944 (6) Å	θ = 1.0–27.5°
b = 19.3719 (10) Å	µ = 4.01 mm−1
c = 7.1241 (3) Å	T = 120 K
β = 111.025 (6)°	Block, orange
V = 1055.60 (10) Å3	0.30 × 0.21 × 0.10 mm
Z = 4

Nonius KappaCCD diffractometer	2423 independent reflections
Radiation source: fine-focus sealed tube	2040 reflections with I > 2σ(I)
horizontally mounted graphite crystal	Rint = 0.032
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 2.7°
φ scans and ω scans with κ offset	h = −10→10
Absorption correction: multi-scan (XPREP in SHELXTL; Sheldrick, 2008)	k = −23→25
Tmin = 0.379, Tmax = 0.699	l = −9→9
13385 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0163P)2 + 1.0004P] where P = (Fo2 + 2Fc2)/3
2423 reflections	(Δ/σ)max = 0.001
119 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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	0.09775 (3)	0.154947 (11)	0.72449 (3)	0.01773 (7)
Cl1	−0.26973 (7)	−0.02283 (3)	1.32107 (8)	0.01820 (12)
Cl2	0.00330 (8)	0.25802 (3)	0.77369 (9)	0.02668 (14)
N1	−0.0543 (3)	0.06371 (10)	1.1409 (3)	0.0188 (4)
H1	−0.119 (4)	0.0437 (15)	1.188 (4)	0.040 (8)*
N2	0.1181 (3)	0.06797 (9)	1.2431 (3)	0.0192 (4)
H2	0.162 (3)	0.0557 (13)	1.359 (4)	0.023 (7)*
C1	0.0658 (3)	0.11191 (10)	0.9452 (3)	0.0144 (4)
C2	−0.0913 (3)	0.08920 (10)	0.9570 (3)	0.0158 (4)
C3	0.1960 (3)	0.09761 (10)	1.1294 (3)	0.0164 (4)
C4	−0.2731 (3)	0.09086 (12)	0.8111 (4)	0.0235 (5)
H4A	−0.3384	0.0512	0.8368	0.028*
H4B	−0.2718	0.0860	0.6733	0.028*
C5	−0.3658 (3)	0.15699 (13)	0.8246 (5)	0.0352 (6)
H5A	−0.3615	0.1634	0.9627	0.053*
H5B	−0.4880	0.1545	0.7333	0.053*
H5C	−0.3082	0.1960	0.7864	0.053*
C6	0.3877 (3)	0.10861 (12)	1.2043 (4)	0.0247 (5)
H6A	0.4335	0.0933	1.1001	0.030*
H6B	0.4428	0.0796	1.3251	0.030*
C7	0.4393 (3)	0.18281 (13)	1.2570 (4)	0.0353 (6)
H7A	0.3884	0.2117	1.1371	0.053*
H7B	0.5670	0.1869	1.3064	0.053*
H7C	0.3960	0.1982	1.3617	0.053*

	U11	U22	U33	U12	U13	U23
Se1	0.02534 (13)	0.01435 (11)	0.01690 (11)	−0.00085 (9)	0.01169 (9)	0.00111 (9)
Cl1	0.0180 (3)	0.0205 (3)	0.0173 (3)	0.0003 (2)	0.0077 (2)	0.0031 (2)
Cl2	0.0454 (4)	0.0144 (3)	0.0276 (3)	0.0047 (2)	0.0220 (3)	0.0042 (2)
N1	0.0212 (11)	0.0159 (9)	0.0228 (10)	−0.0016 (8)	0.0122 (9)	0.0014 (8)
N2	0.0281 (11)	0.0145 (9)	0.0156 (10)	0.0028 (8)	0.0084 (9)	0.0021 (8)
C1	0.0201 (11)	0.0097 (10)	0.0153 (10)	−0.0002 (8)	0.0086 (9)	−0.0004 (8)
C2	0.0209 (12)	0.0095 (9)	0.0194 (11)	0.0004 (8)	0.0101 (10)	−0.0010 (8)
C3	0.0218 (12)	0.0097 (10)	0.0178 (11)	0.0011 (8)	0.0072 (9)	−0.0030 (8)
C4	0.0181 (12)	0.0209 (12)	0.0307 (13)	−0.0004 (9)	0.0076 (10)	−0.0010 (10)
C5	0.0208 (12)	0.0229 (13)	0.0586 (18)	0.0025 (11)	0.0103 (12)	0.0011 (12)
C6	0.0196 (12)	0.0232 (12)	0.0276 (12)	0.0002 (10)	0.0039 (10)	−0.0023 (10)
C7	0.0311 (15)	0.0263 (13)	0.0429 (16)	−0.0088 (11)	0.0063 (13)	−0.0067 (12)

Se1—C1	1.8793 (19)	C4—H4A	0.9900
Se1—Cl2	2.2144 (6)	C4—H4B	0.9900
N1—C2	1.329 (3)	C5—H5A	0.9800
N1—N2	1.339 (3)	C5—H5B	0.9800
N1—H1	0.82 (3)	C5—H5C	0.9800
N2—C3	1.328 (3)	C6—C7	1.507 (3)
N2—H2	0.81 (3)	C6—H6A	0.9900
C1—C3	1.390 (3)	C6—H6B	0.9900
C1—C2	1.391 (3)	C7—H7A	0.9800
C2—C4	1.480 (3)	C7—H7B	0.9800
C3—C6	1.482 (3)	C7—H7C	0.9800
C4—C5	1.510 (3)
C1—Se1—Cl2	96.09 (6)	C5—C4—H4B	109.2
C2—N1—N2	109.64 (18)	H4A—C4—H4B	107.9
C2—N1—H1	129 (2)	C4—C5—H5A	109.5
N2—N1—H1	121 (2)	C4—C5—H5B	109.5
C3—N2—N1	109.82 (19)	H5A—C5—H5B	109.5
C3—N2—H2	128.2 (18)	C4—C5—H5C	109.5
N1—N2—H2	121.9 (18)	H5A—C5—H5C	109.5
C3—C1—C2	107.06 (18)	H5B—C5—H5C	109.5
C3—C1—Se1	126.01 (16)	C3—C6—C7	113.1 (2)
C2—C1—Se1	126.93 (16)	C3—C6—H6A	109.0
N1—C2—C1	106.75 (19)	C7—C6—H6A	109.0
N1—C2—C4	121.10 (19)	C3—C6—H6B	109.0
C1—C2—C4	132.13 (19)	C7—C6—H6B	109.0
N2—C3—C1	106.72 (19)	H6A—C6—H6B	107.8
N2—C3—C6	121.5 (2)	C6—C7—H7A	109.5
C1—C3—C6	131.8 (2)	C6—C7—H7B	109.5
C2—C4—C5	112.1 (2)	H7A—C7—H7B	109.5
C2—C4—H4A	109.2	C6—C7—H7C	109.5
C5—C4—H4A	109.2	H7A—C7—H7C	109.5
C2—C4—H4B	109.2	H7B—C7—H7C	109.5
C2—N1—N2—C3	1.3 (2)	N1—N2—C3—C6	−179.63 (18)
Cl2—Se1—C1—C3	−101.57 (18)	C2—C1—C3—N2	0.0 (2)
Cl2—Se1—C1—C2	77.53 (18)	Se1—C1—C3—N2	179.22 (14)
N2—N1—C2—C1	−1.3 (2)	C2—C1—C3—C6	178.7 (2)
N2—N1—C2—C4	179.96 (18)	Se1—C1—C3—C6	−2.1 (3)
C3—C1—C2—N1	0.8 (2)	N1—C2—C4—C5	90.0 (3)
Se1—C1—C2—N1	−178.43 (15)	C1—C2—C4—C5	−88.4 (3)
C3—C1—C2—C4	179.4 (2)	N2—C3—C6—C7	−105.4 (3)
Se1—C1—C2—C4	0.1 (3)	C1—C3—C6—C7	76.0 (3)
N1—N2—C3—C1	−0.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.82 (3)	2.22 (3)	3.0333 (19)	172 (3)
N2—H2···Cl1i	0.81 (3)	2.22 (3)	3.030 (2)	178 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1	0.82 (3)	2.22 (3)	3.0333 (19)	172 (3)
N2—H2⋯Cl1i	0.81 (3)	2.22 (3)	3.030 (2)	178 (2)

Symmetry code: (i) .