Bis{4-[(3,5-dimethyl-1H-pyrazol-4-yl)selan-yl]-3,5-dimethyl-1H-pyrazol-2-ium} chloride monohydrate.

In the title compound, 2C(10)H(15)N(4)Se(+)·Cl(-)·OH(-), a singly protonated mol-ecule of the organic selenide participates in hydrogen bonding with neighboring mol-ecules, forming zigzag chains along [001]. The molecule adapts a cis bridging mode with a C-Se-C angle of 102.13 (15)°. π-π stacking inter-actions are observed between the closest pyrazole rings of neighboring chains [centroid-centroid distance = 3.888 (1) Å] and hydrogen bonding occurs through bridging chloride anions and hydroxide groups. Additionally, O-H⋯Cl hydrogen bonds are formed.

Related literature

For details and applications of related pyrazoles, see: Krämer & Fritsky (2000 ▶); Fritsky et al. (2004 ▶); Kovbasyuk et al. (2004 ▶); Sachse et al. (2008 ▶); Penkova et al. (2009 ▶8). For structural studies of related bis­(1H-pyrazol-4-yl)selenides, see: Seredyuk et al. (2010a ▶). For structural studies of d-metal complexes of bis­(3,5-dimethyl-1H-pyrazol-4-yl)selenide, see: Seredyuk et al. (2007 ▶, 2009 ▶, 2010b ▶).

Experimental

Crystal data

2C10H15N4Se+·Cl−·HO−

M = 592.90

Monoclinic,

a = 22.805 (2) Å

b = 8.8154 (8) Å

c = 16.7462 (15) Å

β = 131.448 (7)°

V = 2523.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.07 mm−1

T = 100 K

0.25 × 0.20 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.488, T max = 0.698

7656 measured reflections

2926 independent reflections

2211 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.107

S = 1.01

2926 reflections

160 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.15 e Å−3

Δρmin = −0.72 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812025640/rk2354sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025640/rk2354Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025640/rk2354Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812025640/rk2354Isup4.cml

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

2C10H15N4Se+·Cl−·HO−	F(000) = 1200
Mr = 592.90	Dx = 1.561 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3236 reflections
a = 22.805 (2) Å	θ = 3.3–28.3°
b = 8.8154 (8) Å	µ = 3.07 mm−1
c = 16.7462 (15) Å	T = 100 K
β = 131.448 (7)°	Block, colourless
V = 2523.4 (5) Å3	0.25 × 0.20 × 0.12 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	2926 independent reflections
Radiation source: fine-focus sealed tube	2211 reflections with I > 2σ(I)
Flat graphite crystal monochromator	Rint = 0.087
Detector resolution: 16 pixels mm-1	θmax = 28.5°, θmin = 3.3°
φ– and ω–scans	h = −30→30
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→9
Tmin = 0.488, Tmax = 0.698	l = −21→21
7656 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0538P)2] where P = (Fo2 + 2Fc2)/3
2926 reflections	(Δ/σ)max = 0.001
160 parameters	Δρmax = 1.15 e Å−3
0 restraints	Δρmin = −0.72 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.77024 (2)	0.12139 (4)	0.23905 (3)	0.01783 (13)
Cl1	0.5000	0.43772 (14)	0.2500	0.0219 (3)
O1	1.0000	0.5786 (4)	0.2500	0.0268 (9)
H1O	1.0000	0.6625	0.2500	0.040*
N1	0.86540 (17)	0.4303 (3)	0.1726 (2)	0.0181 (7)
H1N1	0.8971	0.4766	0.1798	0.027*
N2	0.78857 (17)	0.4481 (3)	0.0854 (2)	0.0161 (6)
N3	0.73588 (18)	0.3657 (3)	0.4133 (2)	0.0198 (7)
N4	0.66123 (19)	0.3412 (4)	0.3203 (3)	0.0205 (7)
C1	0.9500 (2)	0.2805 (4)	0.3390 (3)	0.0252 (9)
H1A	0.9760	0.2174	0.3240	0.038*
H1B	0.9430	0.2250	0.3815	0.038*
H1C	0.9811	0.3691	0.3772	0.038*
C2	0.8718 (2)	0.3275 (4)	0.2366 (3)	0.0169 (7)
C3	0.7966 (2)	0.2779 (4)	0.1888 (3)	0.0151 (7)
C4	0.7459 (2)	0.3561 (4)	0.0927 (3)	0.0155 (7)
C5	0.6585 (2)	0.3489 (4)	0.0064 (3)	0.0240 (9)
H5A	0.6349	0.4060	0.0277	0.036*
H5B	0.6417	0.2451	−0.0055	0.036*
H5C	0.6429	0.3909	−0.0581	0.036*
C6	0.8690 (2)	0.3080 (5)	0.4851 (3)	0.0251 (9)
H6A	0.8830	0.3557	0.5472	0.038*
H6B	0.8896	0.3660	0.4600	0.038*
H6C	0.8902	0.2072	0.5027	0.038*
C7	0.7813 (2)	0.3004 (4)	0.3993 (3)	0.0173 (7)
C8	0.7356 (2)	0.2344 (4)	0.2981 (3)	0.0160 (7)
C9	0.6587 (2)	0.2626 (4)	0.2498 (3)	0.0182 (8)
C10	0.5831 (2)	0.2243 (4)	0.1410 (3)	0.0263 (9)
H10A	0.5455	0.1925	0.1463	0.039*
H10B	0.5916	0.1439	0.1111	0.039*
H10C	0.5638	0.3122	0.0961	0.039*
H1N4	0.629 (3)	0.372 (5)	0.319 (4)	0.032 (14)*
H1N2	0.769 (2)	0.513 (5)	0.021 (4)	0.037 (12)*

	U11	U22	U33	U12	U13	U23
Se1	0.0250 (2)	0.01211 (19)	0.0227 (2)	0.00254 (15)	0.01847 (18)	0.00275 (15)
Cl1	0.0164 (6)	0.0200 (6)	0.0282 (7)	0.000	0.0143 (6)	0.000
O1	0.029 (2)	0.0157 (18)	0.024 (2)	0.000	0.0128 (19)	0.000
N1	0.0165 (15)	0.0195 (15)	0.0183 (16)	0.0001 (12)	0.0115 (14)	0.0006 (13)
N2	0.0172 (15)	0.0167 (15)	0.0171 (16)	−0.0006 (12)	0.0125 (14)	0.0005 (13)
N3	0.0199 (15)	0.0247 (17)	0.0175 (16)	0.0062 (13)	0.0135 (14)	0.0053 (13)
N4	0.0179 (16)	0.0260 (18)	0.0220 (18)	0.0056 (13)	0.0151 (16)	0.0079 (14)
C1	0.0207 (19)	0.031 (2)	0.022 (2)	0.0051 (16)	0.0131 (18)	0.0058 (17)
C2	0.0171 (18)	0.0192 (17)	0.0178 (19)	0.0003 (14)	0.0129 (16)	−0.0024 (15)
C3	0.0181 (18)	0.0131 (16)	0.0177 (19)	0.0009 (14)	0.0134 (16)	0.0007 (14)
C4	0.0212 (18)	0.0115 (17)	0.0172 (18)	0.0001 (14)	0.0142 (17)	−0.0010 (13)
C5	0.023 (2)	0.023 (2)	0.022 (2)	−0.0016 (16)	0.0137 (18)	0.0037 (16)
C6	0.023 (2)	0.033 (2)	0.018 (2)	0.0052 (17)	0.0126 (18)	0.0010 (17)
C7	0.0185 (18)	0.0176 (18)	0.0202 (19)	0.0046 (14)	0.0147 (16)	0.0070 (15)
C8	0.0215 (18)	0.0144 (17)	0.0195 (18)	0.0054 (14)	0.0167 (17)	0.0076 (14)
C9	0.0216 (18)	0.0177 (18)	0.023 (2)	0.0004 (14)	0.0178 (18)	0.0035 (15)
C10	0.021 (2)	0.031 (2)	0.028 (2)	−0.0020 (17)	0.0162 (19)	0.0033 (18)

Se1—C8	1.904 (4)	C2—C3	1.398 (5)
Se1—C3	1.908 (3)	C3—C4	1.393 (5)
O1—H1O	0.7393	C4—C5	1.500 (5)
N1—C2	1.336 (5)	C5—H5A	0.9600
N1—N2	1.356 (4)	C5—H5B	0.9600
N1—H1N1	0.7666	C5—H5C	0.9600
N2—C4	1.333 (4)	C6—C7	1.504 (5)
N2—H1N2	1.03 (5)	C6—H6A	0.9600
N3—C7	1.333 (4)	C6—H6B	0.9600
N3—N4	1.363 (4)	C6—H6C	0.9600
N4—C9	1.338 (5)	C7—C8	1.400 (5)
N4—H1N4	0.77 (4)	C8—C9	1.384 (5)
C1—C2	1.498 (5)	C9—C10	1.499 (5)
C1—H1A	0.9600	C10—H10A	0.9600
C1—H1B	0.9600	C10—H10B	0.9600
C1—H1C	0.9600	C10—H10C	0.9600
C8—Se1—C3	102.13 (15)	C4—C5—H5B	109.5
C2—N1—N2	108.6 (3)	H5A—C5—H5B	109.5
C2—N1—H1N1	130.1	C4—C5—H5C	109.5
N2—N1—H1N1	121.3	H5A—C5—H5C	109.5
C4—N2—N1	109.4 (3)	H5B—C5—H5C	109.5
C4—N2—H1N2	127 (2)	C7—C6—H6A	109.5
N1—N2—H1N2	124 (2)	C7—C6—H6B	109.5
C7—N3—N4	105.0 (3)	H6A—C6—H6B	109.5
C9—N4—N3	112.4 (3)	C7—C6—H6C	109.5
C9—N4—H1N4	132 (4)	H6A—C6—H6C	109.5
N3—N4—H1N4	115 (4)	H6B—C6—H6C	109.5
C2—C1—H1A	109.5	N3—C7—C8	110.5 (3)
C2—C1—H1B	109.5	N3—C7—C6	120.6 (3)
H1A—C1—H1B	109.5	C8—C7—C6	128.9 (3)
C2—C1—H1C	109.5	C9—C8—C7	105.7 (3)
H1A—C1—H1C	109.5	C9—C8—Se1	126.3 (3)
H1B—C1—H1C	109.5	C7—C8—Se1	127.9 (3)
N1—C2—C3	108.2 (3)	N4—C9—C8	106.3 (3)
N1—C2—C1	121.4 (3)	N4—C9—C10	122.1 (3)
C3—C2—C1	130.4 (3)	C8—C9—C10	131.5 (3)
C4—C3—C2	105.8 (3)	C9—C10—H10A	109.5
C4—C3—Se1	127.2 (3)	C9—C10—H10B	109.5
C2—C3—Se1	126.8 (3)	H10A—C10—H10B	109.5
N2—C4—C3	108.0 (3)	C9—C10—H10C	109.5
N2—C4—C5	121.5 (3)	H10A—C10—H10C	109.5
C3—C4—C5	130.5 (3)	H10B—C10—H10C	109.5
C4—C5—H5A	109.5
C2—N1—N2—C4	−0.7 (4)	Se1—C3—C4—C5	4.3 (6)
C7—N3—N4—C9	0.4 (4)	N4—N3—C7—C8	−0.2 (4)
N2—N1—C2—C3	0.0 (4)	N4—N3—C7—C6	178.2 (3)
N2—N1—C2—C1	178.8 (3)	N3—C7—C8—C9	−0.1 (4)
N1—C2—C3—C4	0.7 (4)	C6—C7—C8—C9	−178.3 (4)
C1—C2—C3—C4	−178.0 (4)	N3—C7—C8—Se1	−177.7 (2)
N1—C2—C3—Se1	175.3 (3)	C6—C7—C8—Se1	4.1 (6)
C1—C2—C3—Se1	−3.3 (6)	C3—Se1—C8—C9	99.9 (3)
C8—Se1—C3—C4	−82.7 (3)	C3—Se1—C8—C7	−83.0 (3)
C8—Se1—C3—C2	103.8 (3)	N3—N4—C9—C8	−0.5 (4)
N1—N2—C4—C3	1.1 (4)	N3—N4—C9—C10	−178.8 (3)
N1—N2—C4—C5	−178.9 (3)	C7—C8—C9—N4	0.3 (4)
C2—C3—C4—N2	−1.1 (4)	Se1—C8—C9—N4	178.0 (3)
Se1—C3—C4—N2	−175.7 (2)	C7—C8—C9—C10	178.5 (4)
C2—C3—C4—C5	178.9 (4)	Se1—C8—C9—C10	−3.9 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1	0.77	2.01	2.747 (3)	161
N4—H1N4···Cl1	0.77 (4)	2.42 (5)	3.146 (3)	160 (5)
O1—H1O···Cl1i	0.74	2.43	3.166 (4)	180
N2—H1N2···N3ii	1.03 (5)	1.78 (5)	2.804 (4)	177 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1W	0.77	2.01	2.747 (3)	161
N4—H1N4⋯Cl1	0.77 (4)	2.42 (5)	3.146 (3)	160 (5)
O1—H1O⋯Cl1i	0.74	2.43	3.166 (4)	180
N2—H1N2⋯N3ii	1.03 (5)	1.78 (5)	2.804 (4)	177 (4)

Symmetry codes: (i) ; (ii) .