Literature DB >> 21202751

1-(4-Chloro-phen-yl)piperazine-1,4-diium tetra-chlorido-zincate(II) monohydrate.

Imen Ben Gharbia, Riadh Kefi, Meher El Glaoui, Erwann Jeanneau, Cherif Ben Nasr.

Abstract

In the crystal structure of the title compound, (C(10)H(15)ClN(2))[ZnCl(4)]·H(2)O, the Zn atom is coordinated by four Cl atoms in a tetrahedral geometry. The water mol-ecules and the 1-(4-chloro-phen-yl)piperazine-1,4-diium cations inter-act with the [ZnCl(4)](2-) anions through O-H⋯Cl, N-H⋯Cl, N-H⋯O and C-H⋯Cl hydrogen bonds (five simple and one bifurcated). Inter-molecular π-π stacking inter-actions are present between adjacent aromatic rings of 1-(4-chloro-phenyl)-piperazine-1,4-diium cations (the centroid-centroid distance is 3.453 Å).

Entities: CellLine Chemical Disease Gene Species

Year: 2008 PMID： 21202751 PMCID： PMC2961817 DOI： 10.1107/S1600536808016590

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For related literature, see: Ben Gharbia et al. (2005 ▶); Guo et al. (2007 ▶); Valkonen et al. (2006 ▶); Janiak (2000 ▶).

Experimental

Crystal data

(C10H15ClN2)[ZnCl4]·H2O M = 423.90 Monoclinic, a = 7.2036 (2) Å b = 15.1575 (5) Å c = 15.4870 (5) Å β = 103.012 (2)° V = 1647.58 (9) Å3 Z = 4 Mo Kα radiation μ = 2.29 mm−1 T = 293 K 0.44 × 0.28 × 0.23 mm

Data collection

Nonius KappaCCD diffractometer Absorption correction: analytical (de Meulenaer & Tompa, 1965 ▶) T min = 0.34, T max = 0.59 20612 measured reflections 3901 independent reflections 3369 reflections with I > 2σ(I) R int = 0.085

Refinement

R[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.063 S = 0.89 3203 reflections 173 parameters H-atom parameters constrained Δρmax = 0.41 e Å−3 Δρmin = −0.69 e Å−3 Data collection: COLLECT (Nonius, 2001 ▶).; cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: CRYSTALS. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016590/bg2190sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016590/bg2190Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C₁₀H₁₅ClN₂)[ZnCl₄]·H₂O	F₀₀₀ = 856
M_r = 423.90	D_x = 1.709 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 19642 reflections
a = 7.2036 (2) Å	θ = 0.7–27.9º
b = 15.1575 (5) Å	µ = 2.29 mm⁻¹
c = 15.4870 (5) Å	T = 293 K
β = 103.012 (2)º	Plate, colorless
V = 1647.58 (9) Å³	0.44 × 0.28 × 0.23 mm
Z = 4

Nonius KappaCCD diffractometer	3369 reflections with I > 2σ(I)
Monochromator: graphite	R_int = 0.085
T = 293 K	θ_max = 28.0º
φ and ω scans	θ_min = 1.9º
Absorption correction: analytical(de Meulenaer & Tompa, 1965)	h = −9→9
T_min = 0.34, T_max = 0.59	k = −17→19
20612 measured reflections	l = −20→20
3901 independent reflections

Refinement on F	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.053	weight = 1.0/[1.57 + 1.32x + 0.866(2x²-1)] * [1-(deltaF/6*sigmaF)²]²where x = F /Fmax
wR(F²) = 0.063	(Δ/σ)_max = 0.0004
S = 0.90	Δρ_max = 0.41 e Å⁻³
3203 reflections	Δρ_min = −0.69 e Å⁻³
173 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	U_iso*/U_eq
Zn1	0.58976 (7)	0.36124 (3)	0.65838 (3)	0.0375
Cl1	0.29500 (16)	0.42310 (8)	0.60275 (7)	0.0461
Cl2	0.75399 (15)	0.36476 (7)	0.54758 (6)	0.0415
Cl3	0.5442 (2)	0.22604 (8)	0.70986 (10)	0.0568
Cl4	0.7715 (2)	0.44230 (9)	0.76618 (7)	0.0560
Cl5	0.29277 (18)	−0.13523 (7)	0.48834 (10)	0.0558
C1	0.2020 (5)	0.1446 (2)	0.4005 (2)	0.0312
C2	0.2558 (6)	0.0844 (3)	0.3443 (3)	0.0410
C3	0.2866 (7)	−0.0026 (3)	0.3717 (3)	0.0442
C4	0.2642 (6)	−0.0255 (3)	0.4557 (3)	0.0404
C5	0.2183 (7)	0.0359 (3)	0.5131 (3)	0.0441
C6	0.1869 (7)	0.1230 (3)	0.4851 (3)	0.0399
C7	−0.0002 (6)	0.2802 (3)	0.3894 (3)	0.0404
C8	−0.0229 (6)	0.3724 (3)	0.3515 (3)	0.0433
C9	0.3249 (7)	0.3838 (3)	0.3692 (3)	0.0468
C10	0.3479 (6)	0.2911 (3)	0.4050 (3)	0.0406
N1	0.1724 (5)	0.2369 (2)	0.3687 (2)	0.0313
N2	0.1516 (6)	0.4259 (2)	0.3875 (3)	0.0466
O1	0.0861 (5)	0.2511 (3)	0.1875 (2)	0.0530
H1	−0.0199	0.2401	0.1574	0.0730*
H2	0.1897	0.2453	0.1746	0.0730*
H3	0.2669	0.1008	0.2869	0.0471*
H4	0.3213	−0.0443	0.3350	0.0503*
H5	0.2084	0.0191	0.5702	0.0511*
H6	0.1563	0.1671	0.5231	0.0473*
H7	−0.1133	0.2465	0.3632	0.0448*
H8	0.0133	0.2821	0.4533	0.0447*
H9	−0.0388	0.3688	0.2866	0.0492*
H10	−0.1329	0.4027	0.3654	0.0493*
H11	0.3148	0.3815	0.3047	0.0543*
H12	0.4375	0.4194	0.3985	0.0543*
H13	0.4580	0.2643	0.3887	0.0434*
H14	0.3750	0.2920	0.4706	0.0430*
H15	0.1556	0.2362	0.3097	0.0410*
H16	0.1361	0.4792	0.3623	0.0620*
H17	0.1605	0.4357	0.4450	0.0620*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0394 (2)	0.0380 (2)	0.0350 (2)	−0.00079 (19)	0.00810 (19)	0.00223 (18)
Cl1	0.0445 (5)	0.0526 (6)	0.0407 (5)	0.0090 (5)	0.0082 (4)	0.0053 (4)
Cl2	0.0449 (5)	0.0428 (5)	0.0392 (5)	−0.0021 (4)	0.0146 (4)	−0.0012 (4)
Cl3	0.0650 (7)	0.0405 (6)	0.0698 (7)	0.0029 (5)	0.0255 (6)	0.0136 (5)
Cl4	0.0704 (7)	0.0562 (7)	0.0350 (5)	−0.0084 (6)	−0.0019 (5)	−0.0027 (4)
Cl5	0.0547 (6)	0.0338 (5)	0.0785 (8)	0.0044 (4)	0.0140 (6)	0.0126 (5)
C1	0.0360 (16)	0.0256 (15)	0.0309 (16)	−0.0002 (14)	0.0055 (14)	−0.0033 (13)
C2	0.048 (2)	0.039 (2)	0.0367 (19)	0.0017 (17)	0.0105 (16)	−0.0033 (16)
C3	0.050 (2)	0.034 (2)	0.047 (2)	0.0069 (17)	0.0085 (18)	−0.0077 (17)
C4	0.0367 (18)	0.0305 (18)	0.051 (2)	0.0021 (15)	0.0034 (16)	0.0003 (16)
C5	0.050 (2)	0.042 (2)	0.041 (2)	0.0025 (18)	0.0112 (17)	0.0089 (17)
C6	0.050 (2)	0.037 (2)	0.0339 (19)	0.0010 (16)	0.0124 (16)	−0.0005 (15)
C7	0.0351 (18)	0.037 (2)	0.051 (2)	0.0050 (15)	0.0128 (16)	0.0027 (17)
C8	0.042 (2)	0.039 (2)	0.049 (2)	0.0095 (17)	0.0085 (17)	0.0014 (17)
C9	0.047 (2)	0.035 (2)	0.054 (2)	−0.0055 (17)	0.0040 (18)	0.0071 (18)
C10	0.0354 (18)	0.033 (2)	0.049 (2)	−0.0031 (15)	0.0012 (16)	0.0045 (16)
N1	0.0391 (16)	0.0263 (14)	0.0274 (13)	0.0008 (12)	0.0055 (12)	0.0007 (11)
N2	0.065 (2)	0.0284 (16)	0.0424 (18)	0.0037 (15)	0.0030 (17)	−0.0020 (13)
O1	0.0519 (18)	0.067 (2)	0.0389 (15)	0.0008 (16)	0.0065 (14)	−0.0023 (14)

Zn1—Cl1	2.3036 (11)	C7—H7	0.970
Zn1—Cl2	2.2937 (11)	C8—N2	1.494 (6)
Zn1—Cl3	2.2495 (13)	C8—H10	0.980
Zn1—Cl4	2.2420 (12)	C8—H9	0.988
Cl5—C4	1.738 (4)	N2—C9	1.485 (7)
C4—C3	1.389 (7)	N2—H16	0.893
C4—C5	1.378 (6)	N2—H17	0.891
C3—C2	1.388 (6)	C9—C10	1.506 (6)
C3—H4	0.922	C9—H12	0.995
C2—C1	1.376 (5)	C9—H11	0.985
C2—H3	0.943	C10—H14	0.990
C1—N1	1.482 (5)	C10—H13	0.973
C1—C6	1.378 (5)	C6—C5	1.392 (6)
N1—C7	1.504 (5)	C6—H6	0.948
N1—C10	1.507 (5)	C5—H5	0.938
N1—H15	0.893	O1—H2	0.820
C7—C8	1.511 (6)	O1—H1	0.818
C7—H8	0.973

Cl1—Zn1—Cl2	107.34 (4)	C7—C8—H10	111.7
Cl1—Zn1—Cl3	107.92 (5)	N2—C8—H10	108.6
Cl2—Zn1—Cl3	115.30 (5)	C7—C8—H9	108.8
Cl1—Zn1—Cl4	112.95 (5)	N2—C8—H9	107.7
Cl2—Zn1—Cl4	103.37 (5)	H10—C8—H9	109.7
Cl3—Zn1—Cl4	110.04 (5)	C8—N2—C9	111.6 (3)
Cl5—C4—C3	118.7 (3)	C8—N2—H16	108.4
Cl5—C4—C5	119.2 (3)	C9—N2—H16	109.4
C3—C4—C5	122.1 (4)	C8—N2—H17	109.2
C4—C3—C2	118.6 (4)	C9—N2—H17	112.9
C4—C3—H4	120.8	H16—N2—H17	105.0
C2—C3—H4	120.6	N2—C9—C10	110.9 (4)
C3—C2—C1	119.0 (4)	N2—C9—H12	108.3
C3—C2—H3	119.7	C10—C9—H12	109.1
C1—C2—H3	121.2	N2—C9—H11	109.6
C2—C1—N1	117.1 (3)	C10—C9—H11	108.5
C2—C1—C6	122.5 (4)	H12—C9—H11	110.5
N1—C1—C6	120.3 (3)	N1—C10—C9	111.0 (3)
C1—N1—C7	113.9 (3)	N1—C10—H14	110.2
C1—N1—C10	110.1 (3)	C9—C10—H14	110.2
C7—N1—C10	110.3 (3)	N1—C10—H13	109.9
C1—N1—H15	107.8	C9—C10—H13	108.7
C7—N1—H15	107.2	H14—C10—H13	106.7
C10—N1—H15	107.3	C1—C6—C5	118.7 (4)
N1—C7—C8	110.1 (3)	C1—C6—H6	120.0
N1—C7—H8	109.4	C5—C6—H6	121.2
C8—C7—H8	110.2	C6—C5—C4	119.0 (4)
N1—C7—H7	109.7	C6—C5—H5	120.7
C8—C7—H7	108.5	C4—C5—H5	120.4
H8—C7—H7	108.9	H2—O1—H1	128.4
C7—C8—N2	110.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H15···O1	0.89	1.86	2.742 (6)	169
N2—H16···Cl4ⁱ	0.89	2.53	3.249 (4)	137
N2—H16···Cl2ⁱ	0.89	2.77	3.352 (3)	123
N2—H17···Cl1	0.89	2.42	3.261 (5)	156
O1—H1···Cl2ⁱⁱ	0.81	2.61	3.342 (3)	149
O1—H2···Cl3ⁱⁱⁱ	0.82	2.52	3.258 (4)	149
C5—H5···Cl4^iv	0.93	2.76	3.686 (5)	168

Table 1

Selected bond lengths (Å)

Zn1—Cl1	2.3036 (11)
Zn1—Cl2	2.2937 (11)
Zn1—Cl3	2.2495 (13)
Zn1—Cl4	2.2420 (12)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H15⋯O1	0.89	1.86	2.742 (6)	169
N2—H16⋯Cl4ⁱ	0.89	2.53	3.249 (4)	137
N2—H16⋯Cl2ⁱ	0.89	2.77	3.352 (3)	123
N2—H17⋯Cl1	0.89	2.42	3.261 (5)	156
O1—H1⋯Cl2ⁱⁱ	0.81	2.61	3.342 (3)	149
O1—H2⋯Cl3ⁱⁱⁱ	0.82	2.52	3.258 (4)	149
C5—H5⋯Cl4^iv	0.93	2.76	3.686 (5)	168

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

1 in total

1. Bis(6-thioxo-1,6-dihydropurinium) tetrachlorozincate(II).

Authors: Arto Valkonen; Kari Ahonen; Erkki Kolehmainen
Journal: Acta Crystallogr C Date: 2006-06-23 Impact factor: 1.172

1 in total