Di-chlorido-{8-[2-(di-methyl-amino)-ethyl-amino]-quinoline-κ(3) N,N',N''}zinc.

In the title complex, [ZnCl2(C13H17N3)], the coordination sphere of the zinc cation is distorted square pyramidal. The three N atoms of the N,N',N''-tridentate 8-[2-(di-methyl-amino)-ethyl-amino]-quinoline ligand and one chloride ion constitute a considerably distorted square base. The apical site is occupied by another chloride ion. The distortion from the ideal square-pyramidal geometry is manifested by the N-Zn-N angle of 133.25 (11)°. Like most square-pyramidal metal complexes, the zinc cation is displaced towards the apical chloride ion. In the crystal, mol-ecules are linked by N-H⋯Cl inter-actions. This leads to the formation of chains of mol-ecules parallel to the b-axis direction.

Related literature

For the role of the zinc cation in biochemical reactions, see: Xu et al. (2010 ▶); Jena & Manivannan (2012 ▶). For the geometry of five-coordinate zinc complexes, see: Dai & Canary (2007 ▶). For a related structure, see: Al-Sudani & Kariuki (2013 ▶).

Experimental

Crystal data

[ZnCl2(C13H17N3)]

M = 351.57

Orthorhombic,

a = 23.6403 (6) Å

b = 7.5682 (2) Å

c = 8.0329 (3) Å

V = 1437.20 (8) Å3

Z = 4

Mo Kα radiation

μ = 2.07 mm−1

T = 150 K

0.17 × 0.05 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.720, T max = 0.922

6701 measured reflections

2638 independent reflections

2422 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.066

S = 1.07

2638 reflections

174 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.38 e Å−3

Absolute structure: Flack (1983 ▶), 873 Friedel pairs

Absolute structure parameter: −0.002 (15)

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012 ▶) and ACD/Chemsketch (Advanced Chemistry Development, 2008 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813029929/hg5348sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813029929/hg5348Isup2.hkl

Additional supporting information: crystallographic information; 3D view; checkCIF report

[ZnCl2(C13H17N3)]	F(000) = 720
Mr = 351.57	Dx = 1.625 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2422 reflections
a = 23.6403 (6) Å	θ = 2.8–27.5°
b = 7.5682 (2) Å	µ = 2.07 mm−1
c = 8.0329 (3) Å	T = 150 K
V = 1437.20 (8) Å3	Block, colourless
Z = 4	0.17 × 0.05 × 0.04 mm

Nonius KappaCCD diffractometer	2638 independent reflections
Radiation source: fine-focus sealed tube	2422 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
CCD slices, ω and phi scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −30→23
Tmin = 0.720, Tmax = 0.922	k = −9→9
6701 measured reflections	l = −8→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030	H-atom parameters constrained
wR(F2) = 0.066	w = 1/[σ2(Fo2) + (0.0224P)2 + 0.8402P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2638 reflections	Δρmax = 0.31 e Å−3
174 parameters	Δρmin = −0.38 e Å−3
1 restraint	Absolute structure: Flack (1983), 873 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.002 (15)

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 > 2σ(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
C1	0.97979 (13)	1.0311 (4)	0.7265 (6)	0.0244 (7)
H1	0.9611	1.1329	0.7685	0.029*
C2	1.03902 (13)	1.0354 (5)	0.7106 (7)	0.0280 (8)
H2	1.0595	1.1380	0.7422	0.034*
C3	1.06704 (15)	0.8905 (5)	0.6491 (5)	0.0267 (9)
H3	1.1069	0.8924	0.6350	0.032*
C4	1.03549 (14)	0.7389 (5)	0.6071 (5)	0.0213 (8)
C5	0.97605 (13)	0.7445 (5)	0.6265 (4)	0.0171 (7)
C6	0.94322 (14)	0.5944 (5)	0.5872 (4)	0.0188 (7)
C7	0.96889 (14)	0.4450 (5)	0.5276 (5)	0.0241 (8)
H7	0.9467	0.3448	0.4992	0.029*
C8	1.02845 (15)	0.4391 (5)	0.5079 (5)	0.0250 (8)
H8	1.0458	0.3344	0.4673	0.030*
C9	1.06105 (15)	0.5815 (5)	0.5466 (5)	0.0232 (8)
H9	1.1009	0.5757	0.5332	0.028*
C10	0.84685 (13)	0.5713 (5)	0.4719 (5)	0.0231 (8)
H10A	0.8454	0.4428	0.4494	0.028*
H10B	0.8617	0.6319	0.3718	0.028*
C11	0.78850 (14)	0.6401 (4)	0.5145 (5)	0.0219 (8)
H11A	0.7627	0.6197	0.4193	0.026*
H11B	0.7735	0.5746	0.6116	0.026*
C12	0.79589 (17)	0.9336 (6)	0.3988 (5)	0.0331 (9)
H12A	0.8311	0.9008	0.3425	0.050*
H12B	0.7966	1.0600	0.4252	0.050*
H12C	0.7637	0.9083	0.3255	0.050*
C13	0.73599 (14)	0.8808 (5)	0.6338 (5)	0.0283 (9)
H13A	0.7348	1.0091	0.6497	0.043*
H13B	0.7330	0.8219	0.7420	0.043*
H13C	0.7044	0.8443	0.5627	0.043*
Cl1	0.83558 (3)	0.77871 (12)	0.97688 (12)	0.02365 (19)
Cl2	0.84770 (3)	1.18659 (10)	0.73045 (17)	0.02760 (19)
N1	0.94882 (11)	0.8923 (3)	0.6858 (3)	0.0183 (7)
N2	0.88348 (11)	0.6075 (4)	0.6168 (4)	0.0179 (6)
H2A	0.8745	0.5245	0.6980	0.021*
N3	0.79023 (12)	0.8311 (4)	0.5534 (4)	0.0199 (6)
Zn1	0.859314 (13)	0.87704 (4)	0.71978 (6)	0.01701 (10)

	U11	U22	U33	U12	U13	U23
C1	0.0281 (15)	0.0196 (16)	0.0254 (17)	−0.0024 (12)	0.000 (2)	−0.002 (2)
C2	0.0242 (15)	0.0246 (18)	0.035 (2)	−0.0062 (13)	−0.002 (2)	−0.001 (2)
C3	0.0205 (16)	0.028 (2)	0.031 (2)	−0.0013 (15)	−0.0014 (16)	−0.0002 (18)
C4	0.0220 (16)	0.025 (2)	0.0166 (17)	−0.0018 (15)	0.0042 (14)	−0.0004 (16)
C5	0.0207 (15)	0.0140 (17)	0.0165 (16)	0.0013 (14)	0.0012 (14)	0.0005 (15)
C6	0.0187 (16)	0.0246 (19)	0.0131 (17)	0.0030 (15)	0.0007 (14)	0.0003 (14)
C7	0.0251 (18)	0.021 (2)	0.026 (2)	0.0027 (16)	0.0005 (16)	−0.0024 (16)
C8	0.0277 (18)	0.0224 (19)	0.025 (2)	0.0068 (16)	0.0032 (16)	−0.0026 (17)
C9	0.0220 (17)	0.026 (2)	0.0214 (19)	0.0028 (16)	0.0027 (15)	0.0012 (16)
C10	0.0215 (16)	0.0243 (19)	0.0236 (18)	0.0005 (14)	−0.0021 (17)	−0.0074 (18)
C11	0.0207 (17)	0.0186 (19)	0.026 (2)	0.0013 (14)	−0.0035 (15)	−0.0046 (16)
C12	0.040 (2)	0.034 (2)	0.025 (2)	0.0058 (19)	−0.0013 (19)	0.0083 (19)
C13	0.0190 (16)	0.032 (2)	0.034 (2)	0.0074 (16)	−0.0038 (16)	−0.0050 (19)
Cl1	0.0250 (4)	0.0253 (4)	0.0207 (4)	−0.0014 (4)	0.0019 (4)	0.0020 (4)
Cl2	0.0258 (3)	0.0148 (4)	0.0422 (5)	0.0004 (3)	0.0018 (6)	−0.0004 (6)
N1	0.0180 (12)	0.0160 (15)	0.021 (2)	−0.0015 (10)	−0.0003 (12)	0.0007 (12)
N2	0.0149 (13)	0.0185 (16)	0.0203 (15)	−0.0007 (12)	−0.0002 (12)	−0.0002 (12)
N3	0.0216 (14)	0.0205 (16)	0.0175 (15)	0.0039 (12)	0.0026 (12)	0.0011 (13)
Zn1	0.01713 (16)	0.01476 (18)	0.01915 (18)	0.00002 (13)	0.0011 (2)	−0.0008 (2)

C1—N1	1.321 (4)	C10—H10A	0.9900
C1—C2	1.406 (4)	C10—H10B	0.9900
C1—H1	0.9500	C11—N3	1.480 (4)
C2—C3	1.373 (5)	C11—H11A	0.9900
C2—H2	0.9500	C11—H11B	0.9900
C3—C4	1.409 (5)	C12—N3	1.470 (5)
C3—H3	0.9500	C12—H12A	0.9800
C4—C5	1.414 (4)	C12—H12B	0.9800
C4—C9	1.421 (5)	C12—H12C	0.9800
C5—N1	1.376 (4)	C13—N3	1.484 (4)
C5—C6	1.412 (5)	C13—H13A	0.9800
C6—C7	1.369 (5)	C13—H13B	0.9800
C6—N2	1.436 (4)	C13—H13C	0.9800
C7—C8	1.418 (5)	Cl1—Zn1	2.2659 (11)
C7—H7	0.9500	Cl2—Zn1	2.3604 (8)
C8—C9	1.361 (5)	N1—Zn1	2.136 (3)
C8—H8	0.9500	N2—Zn1	2.274 (3)
C9—H9	0.9500	N2—H2A	0.9300
C10—N2	1.476 (5)	N3—Zn1	2.139 (3)
C10—C11	1.513 (4)
N1—C1—C2	123.2 (3)	H11A—C11—H11B	108.0
N1—C1—H1	118.4	N3—C12—H12A	109.5
C2—C1—H1	118.4	N3—C12—H12B	109.5
C3—C2—C1	119.6 (3)	H12A—C12—H12B	109.5
C3—C2—H2	120.2	N3—C12—H12C	109.5
C1—C2—H2	120.2	H12A—C12—H12C	109.5
C2—C3—C4	118.7 (3)	H12B—C12—H12C	109.5
C2—C3—H3	120.6	N3—C13—H13A	109.5
C4—C3—H3	120.6	N3—C13—H13B	109.5
C3—C4—C5	118.4 (3)	H13A—C13—H13B	109.5
C3—C4—C9	122.6 (3)	N3—C13—H13C	109.5
C5—C4—C9	119.0 (3)	H13A—C13—H13C	109.5
N1—C5—C6	118.3 (3)	H13B—C13—H13C	109.5
N1—C5—C4	121.8 (3)	C1—N1—C5	118.2 (3)
C6—C5—C4	119.8 (3)	C1—N1—Zn1	124.1 (2)
C7—C6—C5	119.9 (3)	C5—N1—Zn1	117.6 (2)
C7—C6—N2	123.4 (3)	C6—N2—C10	115.7 (3)
C5—C6—N2	116.6 (3)	C6—N2—Zn1	111.7 (2)
C6—C7—C8	120.3 (3)	C10—N2—Zn1	107.8 (2)
C6—C7—H7	119.8	C6—N2—H2A	107.1
C8—C7—H7	119.8	C10—N2—H2A	107.1
C9—C8—C7	120.8 (3)	Zn1—N2—H2A	107.1
C9—C8—H8	119.6	C12—N3—C11	109.8 (3)
C7—C8—H8	119.6	C12—N3—C13	108.2 (3)
C8—C9—C4	120.1 (3)	C11—N3—C13	108.4 (3)
C8—C9—H9	120.0	C12—N3—Zn1	111.9 (2)
C4—C9—H9	120.0	C11—N3—Zn1	108.2 (2)
N2—C10—C11	107.0 (3)	C13—N3—Zn1	110.3 (2)
N2—C10—H10A	110.3	N1—Zn1—N3	133.25 (11)
C11—C10—H10A	110.3	N1—Zn1—Cl1	112.30 (8)
N2—C10—H10B	110.3	N3—Zn1—Cl1	109.10 (8)
C11—C10—H10B	110.3	N1—Zn1—N2	75.72 (10)
H10A—C10—H10B	108.6	N3—Zn1—N2	79.56 (10)
N3—C11—C10	111.0 (3)	Cl1—Zn1—N2	95.69 (8)
N3—C11—H11A	109.4	N1—Zn1—Cl2	93.79 (8)
C10—C11—H11A	109.4	N3—Zn1—Cl2	95.46 (8)
N3—C11—H11B	109.4	Cl1—Zn1—Cl2	105.31 (4)
C10—C11—H11B	109.4	N2—Zn1—Cl2	158.87 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl2i	0.93	2.65	3.420 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl2i	0.93	2.65	3.420 (3)	141

Symmetry code: (i) .