Literature DB >> 21582379

Bis(2,5-dimethyl-anilinium) tetra-chlorido-zincate(II).

Sofiane Souissi¹, Wajda Smirani, Mohamed Rzaigui.

Abstract

In the title compound, (C(8)H(12)N)(2)[n class="Chemical">ZnCl(4)], the Zn(2+) ion adopts a distorted tetra-hedral coordination geometry. In the crystal, the cations and anions are linked by N-H⋯Cl hydrogen bonds, leading to ribbons propagating parallel to the a axis.

Entities: CellLine Chemical Disease Gene Species

Year: 2009 PMID： 21582379 PMCID： PMC2968953 DOI： 10.1107/S1600536809009982

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

Related literature

For related structures, see: Guo et al. (2007 ▶); Smirani & Rzaigui (2009 ▶). For background on hybrid materials, see: Tao et al. (2003 ▶); Bringley & Rajeswaran (2006 ▶).

Experimental

Crystal data

(C8H12N)2[ZnCl4] M = 451.58 Monoclinic, a = 7.425 (2) Å b = 12.884 (2) Å c = 22.809 (2) Å β = 96.16 (2)° V = 2169.5 (7) Å3 Z = 4 Mo Kα radiation μ = 1.62 mm−1 T = 293 K 0.20 × 0.13 × 0.10 mm

Data collection

Enraf–Nonius Turbo CAD-4 diffractometer Absorption correction: none 6539 measured reflections 3947 independent reflections 2621 reflections with I > 2σ(I) R int = 0.033 2 standard reflections frequency: 120 min intensity decay: 5%

Refinement

R[F 2 > 2σ(F 2)] = 0.079 wR(F 2) = 0.229 S = 1.05 3947 reflections 214 parameters H-atom parameters not refined Δρmax = 0.50 e Å−3 Δρmin = −0.61 e Å−3 Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809009982/hb2930sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009982/hb2930Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C₈H₁₂N)₂[ZnCl₄]	F(000) = 928
M_r = 451.58	D_x = 1.383 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 7.425 (2) Å	θ = 9.9–11.0°
b = 12.884 (2) Å	µ = 1.62 mm⁻¹
c = 22.809 (2) Å	T = 293 K
β = 96.16 (2)°	Block, colourless
V = 2169.5 (7) Å³	0.20 × 0.13 × 0.10 mm
Z = 4

Enraf–Nonius Turbo CAD-4 diffractometer	θ_max = 28.0°, θ_min = 2.4°
Radiation source: Enraf Nonius FR590	h = −9→9
Nonprofiled ω scans	k = 0→17
6539 measured reflections	l = −10→17
3947 independent reflections	2 standard reflections every 120 min
2621 reflections with I > 2σ(I)	intensity decay: 5%
R_int = 0.033

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.229	H-atom parameters not refined
S = 1.05	w = 1/[σ²(F_o²) + (0.1531P)²] where P = (F_o² + 2F_c²)/3
3947 reflections	(Δ/σ)_max = 0.012
214 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.61 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	U_iso*/U_eq
Cl1	0.0360 (2)	0.16857 (16)	0.12060 (10)	0.0688 (6)
Cl2	0.52806 (19)	0.20922 (13)	0.10654 (9)	0.0537 (5)
Cl3	0.1904 (2)	0.22519 (13)	−0.02438 (9)	0.0583 (6)
Cl4	0.3103 (3)	−0.02537 (13)	0.04807 (11)	0.0808 (7)
N1	0.2378 (7)	0.7499 (4)	−0.0004 (3)	0.0562 (16)
H1A	0.2629	0.8096	0.0183	0.084*
H1B	0.1189	0.7451	−0.0105	0.084*
H1C	0.2950	0.7474	−0.0328	0.084*
C1	0.2981 (7)	0.6631 (4)	0.0386 (3)	0.0414 (17)
C3	0.3769 (8)	0.6844 (4)	0.0940 (3)	0.0490 (19)
H3	0.3922	0.7531	0.1061	0.059*
C4	0.4345 (8)	0.6053 (5)	0.1327 (3)	0.0527 (18)
C2	0.2704 (7)	0.5621 (4)	0.0171 (3)	0.0407 (16)
C5	0.3295 (8)	0.4834 (4)	0.0569 (3)	0.0513 (19)
H5	0.3153	0.4146	0.0451	0.062*
C9	0.1839 (10)	0.5398 (6)	−0.0438 (3)	0.062 (2)
H9A	0.0653	0.5703	−0.0490	0.093*
H9B	0.1742	0.4661	−0.0495	0.093*
H9C	0.2567	0.5686	−0.0721	0.093*
C8	0.4080 (9)	0.5049 (5)	0.1130 (4)	0.0530 (19)
H8	0.4441	0.4502	0.1382	0.064*
C7	0.5214 (14)	0.6282 (7)	0.1943 (4)	0.086 (3)
H7A	0.6431	0.6522	0.1925	0.129*
H7B	0.5235	0.5661	0.2177	0.129*
H7C	0.4529	0.6808	0.2119	0.129*
N2	−0.2368 (8)	0.9737 (4)	0.1100 (3)	0.0565 (17)
H2A	−0.1525	1.0231	0.1114	0.085*
H2B	−0.3429	0.9999	0.0952	0.085*
H2C	−0.2061	0.9220	0.0872	0.085*
C10	−0.2512 (9)	0.9346 (4)	0.1696 (3)	0.0456 (17)
C13	−0.1163 (9)	0.8706 (5)	0.1964 (3)	0.0483 (19)
C11	−0.3993 (9)	0.9637 (6)	0.1974 (4)	0.062 (2)
H11	−0.4863	1.0074	0.1782	0.075*
C14	0.0465 (11)	0.8399 (7)	0.1675 (4)	0.082 (3)
H14A	0.0186	0.7799	0.1433	0.123*
H14B	0.1443	0.8240	0.1971	0.123*
H14C	0.0813	0.8961	0.1434	0.123*
C12	−0.4195 (10)	0.9281 (7)	0.2541 (4)	0.065 (2)
C16	−0.2860 (11)	0.8619 (6)	0.2797 (4)	0.062 (2)
H16	−0.2972	0.8346	0.3169	0.075*
C15	−0.1412 (11)	0.8360 (6)	0.2523 (4)	0.062 (2)
H15	−0.0538	0.7929	0.2718	0.075*
C17	−0.5803 (14)	0.9593 (10)	0.2849 (5)	0.120 (4)
H17A	−0.6893	0.9349	0.2627	0.180*
H17B	−0.5844	1.0335	0.2879	0.180*
H17C	−0.5701	0.9293	0.3236	0.180*
Zn1	0.26302 (8)	0.14604 (5)	0.06412 (4)	0.0418 (3)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0506 (9)	0.0874 (13)	0.0709 (18)	0.0007 (8)	0.0174 (9)	−0.0083 (11)
Cl2	0.0423 (7)	0.0579 (9)	0.0584 (15)	−0.0086 (6)	−0.0064 (7)	−0.0055 (8)
Cl3	0.0709 (10)	0.0511 (9)	0.0506 (16)	−0.0023 (7)	−0.0040 (9)	0.0047 (8)
Cl4	0.1136 (16)	0.0354 (8)	0.0909 (19)	−0.0001 (9)	−0.0004 (13)	−0.0092 (9)
N1	0.067 (3)	0.039 (3)	0.063 (5)	0.003 (2)	0.004 (3)	0.008 (3)
C1	0.036 (3)	0.033 (3)	0.056 (6)	0.003 (2)	0.012 (3)	0.003 (3)
C3	0.047 (3)	0.036 (3)	0.063 (6)	0.000 (2)	0.001 (3)	−0.004 (3)
C4	0.048 (3)	0.052 (3)	0.057 (6)	−0.001 (3)	−0.001 (3)	0.004 (3)
C2	0.037 (3)	0.041 (3)	0.046 (5)	−0.004 (2)	0.012 (3)	−0.001 (3)
C5	0.047 (3)	0.033 (3)	0.076 (6)	−0.001 (2)	0.011 (3)	0.005 (3)
C9	0.066 (4)	0.056 (4)	0.064 (7)	−0.008 (3)	0.006 (4)	−0.012 (4)
C8	0.053 (3)	0.042 (3)	0.063 (6)	0.005 (3)	0.000 (4)	0.008 (3)
C7	0.101 (7)	0.075 (5)	0.077 (8)	−0.001 (5)	−0.014 (6)	0.001 (5)
N2	0.075 (4)	0.054 (3)	0.041 (5)	0.004 (3)	0.005 (3)	0.008 (3)
C10	0.060 (4)	0.047 (3)	0.029 (5)	−0.006 (3)	0.000 (3)	0.001 (3)
C13	0.057 (4)	0.053 (3)	0.033 (6)	−0.003 (3)	−0.004 (3)	0.001 (3)
C11	0.058 (4)	0.069 (4)	0.058 (7)	0.013 (3)	−0.003 (4)	0.000 (4)
C14	0.068 (5)	0.109 (7)	0.067 (8)	0.026 (5)	0.002 (5)	−0.002 (5)
C12	0.067 (4)	0.087 (5)	0.042 (7)	−0.006 (4)	0.012 (4)	−0.002 (4)
C16	0.075 (5)	0.076 (5)	0.034 (6)	−0.009 (4)	−0.001 (4)	0.009 (4)
C15	0.068 (5)	0.065 (4)	0.051 (7)	0.006 (3)	−0.008 (4)	0.007 (4)
C17	0.085 (6)	0.195 (13)	0.082 (9)	0.028 (7)	0.020 (6)	−0.011 (8)
Zn1	0.0383 (4)	0.0382 (4)	0.0481 (8)	−0.0011 (3)	0.0007 (3)	−0.0031 (3)

Zn1—Cl1	2.248 (2)	C7—H7B	0.9600
Zn1—Cl2	2.2502 (16)	C7—H7C	0.9600
Zn1—Cl3	2.274 (2)	N2—C10	1.463 (9)
Zn1—Cl4	2.2721 (18)	N2—H2A	0.8900
N1—C1	1.468 (8)	N2—H2B	0.8900
N1—H1A	0.8900	N2—H2C	0.8900
N1—H1B	0.8900	C10—C11	1.379 (10)
N1—H1C	0.8900	C10—C13	1.388 (9)
C1—C3	1.364 (10)	C13—C15	1.382 (11)
C1—C2	1.399 (8)	C13—C14	1.491 (11)
C3—C4	1.386 (9)	C11—C12	1.396 (11)
C3—H3	0.9300	C11—H11	0.9300
C4—C8	1.377 (9)	C14—H14A	0.9600
C4—C7	1.512 (11)	C14—H14B	0.9600
C2—C5	1.400 (9)	C14—H14C	0.9600
C2—C9	1.495 (10)	C12—C16	1.388 (11)
C5—C8	1.376 (10)	C12—C17	1.503 (13)
C5—H5	0.9300	C16—C15	1.343 (12)
C9—H9A	0.9600	C16—H16	0.9300
C9—H9B	0.9600	C15—H15	0.9300
C9—H9C	0.9600	C17—H17A	0.9600
C8—H8	0.9300	C17—H17B	0.9600
C7—H7A	0.9600	C17—H17C	0.9600

C1—N1—H1A	109.5	C10—N2—H2C	109.5
C1—N1—H1B	109.5	H2A—N2—H2C	109.5
H1A—N1—H1B	109.5	H2B—N2—H2C	109.5
C1—N1—H1C	109.5	C11—C10—C13	122.2 (7)
H1A—N1—H1C	109.5	C11—C10—N2	118.4 (6)
H1B—N1—H1C	109.5	C13—C10—N2	119.5 (6)
C3—C1—C2	123.0 (6)	C15—C13—C10	115.9 (7)
C3—C1—N1	118.8 (5)	C15—C13—C14	121.2 (7)
C2—C1—N1	118.2 (6)	C10—C13—C14	122.9 (7)
C1—C3—C4	121.0 (6)	C10—C11—C12	120.5 (7)
C1—C3—H3	119.5	C10—C11—H11	119.8
C4—C3—H3	119.5	C12—C11—H11	119.8
C8—C4—C3	117.4 (7)	C13—C14—H14A	109.5
C8—C4—C7	121.2 (7)	C13—C14—H14B	109.5
C3—C4—C7	121.3 (7)	H14A—C14—H14B	109.5
C1—C2—C5	115.0 (6)	C13—C14—H14C	109.5
C1—C2—C9	122.5 (6)	H14A—C14—H14C	109.5
C5—C2—C9	122.5 (6)	H14B—C14—H14C	109.5
C8—C5—C2	122.0 (6)	C16—C12—C11	116.7 (7)
C8—C5—H5	119.0	C16—C12—C17	122.3 (9)
C2—C5—H5	119.0	C11—C12—C17	121.0 (8)
C2—C9—H9A	109.5	C15—C16—C12	121.8 (8)
C2—C9—H9B	109.5	C15—C16—H16	119.1
H9A—C9—H9B	109.5	C12—C16—H16	119.1
C2—C9—H9C	109.5	C16—C15—C13	122.9 (7)
H9A—C9—H9C	109.5	C16—C15—H15	118.5
H9B—C9—H9C	109.5	C13—C15—H15	118.5
C5—C8—C4	121.6 (6)	C12—C17—H17A	109.5
C5—C8—H8	119.2	C12—C17—H17B	109.5
C4—C8—H8	119.2	H17A—C17—H17B	109.5
C4—C7—H7A	109.5	C12—C17—H17C	109.5
C4—C7—H7B	109.5	H17A—C17—H17C	109.5
H7A—C7—H7B	109.5	H17B—C17—H17C	109.5
C4—C7—H7C	109.5	Cl1—Zn1—Cl2	112.46 (8)
H7A—C7—H7C	109.5	Cl1—Zn1—Cl4	110.87 (9)
H7B—C7—H7C	109.5	Cl2—Zn1—Cl4	106.13 (8)
C10—N2—H2A	109.5	Cl1—Zn1—Cl3	109.26 (8)
C10—N2—H2B	109.5	Cl2—Zn1—Cl3	109.42 (7)
H2A—N2—H2B	109.5	Cl4—Zn1—Cl3	108.59 (9)

C2—C1—C3—C4	−0.1 (9)	C11—C10—C13—C15	1.3 (10)
N1—C1—C3—C4	179.4 (6)	N2—C10—C13—C15	−179.2 (6)
C1—C3—C4—C8	−0.4 (10)	C11—C10—C13—C14	−178.8 (7)
C1—C3—C4—C7	−179.8 (7)	N2—C10—C13—C14	0.7 (10)
C3—C1—C2—C5	0.1 (8)	C13—C10—C11—C12	−0.7 (11)
N1—C1—C2—C5	−179.3 (5)	N2—C10—C11—C12	179.7 (6)
C3—C1—C2—C9	−180.0 (6)	C10—C11—C12—C16	−1.0 (11)
N1—C1—C2—C9	0.6 (9)	C10—C11—C12—C17	180.0 (9)
C1—C2—C5—C8	0.3 (9)	C11—C12—C16—C15	2.2 (12)
C9—C2—C5—C8	−179.6 (6)	C17—C12—C16—C15	−178.7 (9)
C2—C5—C8—C4	−0.8 (10)	C12—C16—C15—C13	−1.8 (12)
C3—C4—C8—C5	0.8 (10)	C10—C13—C15—C16	0.0 (11)
C7—C4—C8—C5	−179.8 (7)	C14—C13—C15—C16	−179.9 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl4ⁱ	0.89	2.25	3.125 (6)	169
N1—H1B···Cl3ⁱⁱ	0.89	2.54	3.304 (6)	145
N1—H1C···Cl2ⁱⁱⁱ	0.89	2.31	3.172 (7)	162
N2—H2A···Cl1ⁱ	0.89	2.34	3.219 (6)	171
N2—H2B···Cl4^iv	0.89	2.70	3.505 (7)	151
N2—H2C···Cl3ⁱⁱ	0.89	2.39	3.262 (6)	168

Table 1

Selected bond lengths (Å)

Zn1—Cl1	2.248 (2)
Zn1—Cl2	2.2502 (16)
Zn1—Cl3	2.274 (2)
Zn1—Cl4	2.2721 (18)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl4ⁱ	0.89	2.25	3.125 (6)	169
N1—H1B⋯Cl3ⁱⁱ	0.89	2.54	3.304 (6)	145
N1—H1C⋯Cl2ⁱⁱⁱ	0.89	2.31	3.172 (7)	162
N2—H2A⋯Cl1ⁱ	0.89	2.34	3.219 (6)	171
N2—H2B⋯Cl4^iv	0.89	2.70	3.505 (7)	151
N2—H2C⋯Cl3ⁱⁱ	0.89	2.39	3.262 (6)	168

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

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. 2,5-Dimethyl-anilinium chloride monohydrate.

Authors: Wajda Smirani; Mohamed Rzaigui
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-12-10

2 in total

1 in total

1. 2,5-Dimethyl-anilinium nitrate.

Authors: Wajda Smirani; Mohamed Rzaigui
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-07-18

1 in total