8-Hy-droxy-2-methyl-quinolinium diiodido(2-methyl-quinolin-8-olato-κN,O)zincate.

The reaction of 2-methyl-8-hy-droxy-quinoline and zinc iodide in acetonitrile affords the title salt, (C(10)H(10)NO)[Zn(C(10)H(8)NO)I(2)], in which the Zn(II) ion is coordinated by a N,O-chelating 2-methyl-quinolin-8-olate ligand and two iodide ligands in a distorted tetra-hedral geometry. The cation is linked to the anion by an O-H⋯O hydrogen bond.

Related literature

For the crystal structures of two related 8-hy­droxy-2-methyl­quinolinium dihalo(2-methyl­quinolin-8-olato)zincate aceto­nitrile solvates, see: Najafi et al. (2011a ▶,b ▶). For the crystal structures of related methanol solvates, see: Najafi et al. (2010a ▶,b ▶); Sattarzadeh et al. (2009 ▶).

Experimental

Crystal data

(C10H10NO)[Zn(C10H8NO)I2]

M = 637.53

Monoclinic,

a = 8.1794 (2) Å

b = 13.9441 (3) Å

c = 9.1838 (2) Å

β = 102.503 (3)°

V = 1022.61 (4) Å3

Z = 2

Mo Kα radiation

μ = 4.24 mm−1

T = 100 K

0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.282, T max = 0.485

4995 measured reflections

3765 independent reflections

3692 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.087

S = 1.04

3765 reflections

247 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.99 e Å−3

Δρmin = −1.53 e Å−3

Absolute structure: Flack (1983 ▶) 1389 Friedel pairs

Flack parameter: 0.01 (2)

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032351/lh5307sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032351/lh5307Isup2.hkl

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

(C10H10NO)[Zn(C10H8NO)I2]	F(000) = 608
Mr = 637.53	Dx = 2.070 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4585 reflections
a = 8.1794 (2) Å	θ = 2.6–26.3°
b = 13.9441 (3) Å	µ = 4.24 mm−1
c = 9.1838 (2) Å	T = 100 K
β = 102.503 (3)°	Block, yellow
V = 1022.61 (4) Å3	0.40 × 0.30 × 0.20 mm
Z = 2

Agilent SuperNova Dual diffractometer with an Atlas detector	3765 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3692 reflections with I > 2σ(I)
Mirror	Rint = 0.025
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.6°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −17→18
Tmin = 0.282, Tmax = 0.485	l = −11→7
4995 measured reflections

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0676P)2 + 0.3294P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3765 reflections	Δρmax = 0.99 e Å−3
247 parameters	Δρmin = −1.53 e Å−3
1 restraint	Absolute structure: Flack (1983) 1389 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (2)

	x	y	z	Uiso*/Ueq
I1	0.34742 (4)	0.50002 (2)	0.27609 (4)	0.01513 (10)
I2	0.86547 (4)	0.57723 (3)	0.30050 (4)	0.01526 (10)
Zn1	0.65211 (7)	0.50245 (5)	0.42920 (6)	0.01153 (14)
O1	0.7152 (5)	0.3768 (3)	0.5317 (4)	0.0140 (8)
O2	0.7800 (6)	0.2102 (3)	0.4468 (5)	0.0185 (9)
H2O	0.7556	0.2669	0.4645	0.028*
N1	0.6329 (6)	0.5443 (4)	0.6384 (6)	0.0128 (10)
N2	0.8374 (6)	0.0372 (4)	0.3439 (6)	0.0124 (10)
H2N	0.7921	0.0452	0.4217	0.015*
C1	0.6269 (7)	0.4639 (5)	0.7234 (7)	0.0118 (12)
C2	0.6735 (7)	0.3762 (5)	0.6652 (6)	0.0127 (11)
C3	0.6735 (8)	0.2940 (5)	0.7488 (7)	0.0164 (12)
H3	0.7045	0.2344	0.7126	0.020*
C4	0.6277 (7)	0.2983 (5)	0.8879 (7)	0.0180 (12)
H4	0.6277	0.2407	0.9431	0.022*
C5	0.5831 (8)	0.3824 (5)	0.9472 (7)	0.0176 (12)
H5	0.5521	0.3831	1.0411	0.021*
C6	0.5844 (7)	0.4686 (5)	0.8641 (7)	0.0134 (12)
C7	0.5476 (7)	0.5605 (5)	0.9138 (6)	0.0163 (14)
H7	0.5153	0.5670	1.0067	0.020*
C8	0.5583 (8)	0.6396 (5)	0.8297 (7)	0.0156 (12)
H8	0.5373	0.7014	0.8654	0.019*
C9	0.6008 (8)	0.6297 (5)	0.6886 (7)	0.0134 (13)
C10	0.6195 (8)	0.7153 (4)	0.5938 (7)	0.0160 (12)
H10A	0.5744	0.7723	0.6337	0.024*
H10B	0.5580	0.7040	0.4912	0.024*
H10C	0.7383	0.7254	0.5947	0.024*
C11	0.8860 (8)	0.1179 (5)	0.2762 (7)	0.0137 (12)
C12	0.8575 (8)	0.2094 (5)	0.3348 (8)	0.0144 (12)
C13	0.9136 (8)	0.2891 (4)	0.2680 (7)	0.0164 (12)
H13	0.8988	0.3516	0.3043	0.020*
C14	0.9923 (8)	0.2774 (5)	0.1470 (7)	0.0190 (13)
H14	1.0315	0.3328	0.1049	0.023*
C15	1.0147 (8)	0.1899 (5)	0.0878 (7)	0.0179 (12)
H15	1.0655	0.1847	0.0044	0.021*
C16	0.9607 (8)	0.1066 (4)	0.1530 (7)	0.0133 (12)
C17	0.9785 (8)	0.0115 (5)	0.1023 (7)	0.0172 (12)
H17	1.0273	0.0012	0.0187	0.021*
C18	0.9261 (8)	−0.0647 (4)	0.1728 (7)	0.0156 (12)
H18	0.9374	−0.1278	0.1372	0.019*
C19	0.8552 (7)	−0.0510 (6)	0.2982 (7)	0.0130 (15)
C20	0.8021 (8)	−0.1330 (5)	0.3803 (7)	0.0187 (12)
H20A	0.7757	−0.1098	0.4733	0.028*
H20B	0.8930	−0.1800	0.4033	0.028*
H20C	0.7027	−0.1631	0.3186	0.028*

	U11	U22	U33	U12	U13	U23
I1	0.01258 (17)	0.01704 (18)	0.01573 (17)	−0.00109 (15)	0.00297 (12)	0.00069 (15)
I2	0.01426 (17)	0.01766 (18)	0.01540 (17)	−0.00195 (15)	0.00660 (12)	0.00132 (15)
Zn1	0.0134 (3)	0.0116 (3)	0.0105 (3)	0.0006 (3)	0.0048 (2)	0.0002 (3)
O1	0.021 (2)	0.0107 (18)	0.012 (2)	0.0033 (17)	0.0093 (16)	0.0002 (16)
O2	0.025 (2)	0.0118 (19)	0.022 (2)	0.0044 (18)	0.0115 (18)	−0.0004 (17)
N1	0.012 (2)	0.014 (2)	0.013 (2)	−0.001 (2)	0.0035 (18)	0.003 (2)
N2	0.013 (2)	0.013 (2)	0.012 (2)	0.003 (2)	0.0051 (19)	−0.001 (2)
C1	0.010 (3)	0.013 (3)	0.012 (3)	−0.001 (2)	0.002 (2)	0.001 (2)
C2	0.011 (3)	0.017 (3)	0.010 (3)	−0.002 (2)	0.003 (2)	0.000 (2)
C3	0.017 (3)	0.011 (3)	0.020 (3)	0.002 (2)	0.003 (2)	0.000 (2)
C4	0.019 (3)	0.016 (3)	0.019 (3)	−0.001 (3)	0.006 (2)	0.008 (2)
C5	0.021 (3)	0.021 (3)	0.013 (3)	−0.005 (3)	0.007 (2)	0.000 (2)
C6	0.012 (3)	0.013 (3)	0.015 (3)	−0.001 (2)	0.002 (2)	0.000 (2)
C7	0.020 (3)	0.022 (4)	0.008 (3)	0.001 (3)	0.005 (2)	−0.003 (2)
C8	0.018 (3)	0.012 (3)	0.017 (3)	−0.002 (2)	0.004 (2)	−0.004 (2)
C9	0.012 (3)	0.012 (3)	0.016 (3)	0.007 (3)	0.004 (2)	0.003 (2)
C10	0.017 (3)	0.013 (3)	0.018 (3)	0.003 (2)	0.004 (2)	0.001 (2)
C11	0.012 (3)	0.013 (3)	0.016 (3)	0.003 (2)	0.002 (2)	0.000 (2)
C12	0.012 (3)	0.015 (3)	0.014 (3)	0.001 (2)	−0.001 (2)	−0.002 (2)
C13	0.019 (3)	0.013 (3)	0.017 (3)	−0.001 (2)	0.005 (2)	0.001 (2)
C14	0.021 (3)	0.018 (3)	0.019 (3)	−0.002 (2)	0.004 (2)	0.001 (2)
C15	0.018 (3)	0.023 (3)	0.014 (3)	−0.001 (3)	0.008 (2)	0.001 (2)
C16	0.011 (2)	0.013 (3)	0.015 (3)	0.003 (2)	0.002 (2)	−0.001 (2)
C17	0.014 (3)	0.020 (3)	0.018 (3)	0.003 (3)	0.005 (2)	−0.006 (3)
C18	0.019 (3)	0.011 (3)	0.016 (3)	0.006 (2)	0.005 (2)	−0.004 (2)
C19	0.016 (3)	0.013 (3)	0.010 (3)	0.003 (2)	0.002 (2)	−0.001 (2)
C20	0.022 (3)	0.016 (3)	0.019 (3)	−0.001 (2)	0.006 (2)	−0.001 (2)

I1—Zn1	2.5831 (7)	C8—C9	1.420 (9)
I2—Zn1	2.5343 (7)	C8—H8	0.9500
Zn1—O1	2.003 (4)	C9—C10	1.505 (9)
Zn1—N1	2.046 (5)	C10—H10A	0.9800
O1—C2	1.342 (7)	C10—H10B	0.9800
O2—C12	1.320 (8)	C10—H10C	0.9800
O2—H2O	0.8400	C11—C16	1.406 (9)
N1—C9	1.323 (8)	C11—C12	1.423 (9)
N1—C1	1.373 (8)	C12—C13	1.394 (9)
N2—C19	1.317 (9)	C13—C14	1.409 (8)
N2—C11	1.386 (8)	C13—H13	0.9500
N2—H2N	0.8800	C14—C15	1.365 (9)
C1—C6	1.410 (9)	C14—H14	0.9500
C1—C2	1.420 (9)	C15—C16	1.420 (9)
C2—C3	1.380 (9)	C15—H15	0.9500
C3—C4	1.407 (8)	C16—C17	1.423 (9)
C3—H3	0.9500	C17—C18	1.362 (9)
C4—C5	1.376 (9)	C17—H17	0.9500
C4—H4	0.9500	C18—C19	1.409 (8)
C5—C6	1.424 (9)	C18—H18	0.9500
C5—H5	0.9500	C19—C20	1.486 (9)
C6—C7	1.415 (9)	C20—H20A	0.9800
C7—C8	1.360 (9)	C20—H20B	0.9800
C7—H7	0.9500	C20—H20C	0.9800
O1—Zn1—N1	82.69 (19)	C8—C9—C10	121.8 (6)
O1—Zn1—I2	116.46 (12)	C9—C10—H10A	109.5
N1—Zn1—I2	121.41 (14)	C9—C10—H10B	109.5
O1—Zn1—I1	111.38 (13)	H10A—C10—H10B	109.5
N1—Zn1—I1	104.68 (14)	C9—C10—H10C	109.5
I2—Zn1—I1	115.60 (3)	H10A—C10—H10C	109.5
C2—O1—Zn1	110.1 (3)	H10B—C10—H10C	109.5
C12—O2—H2O	109.5	N2—C11—C16	119.1 (6)
C9—N1—C1	120.2 (5)	N2—C11—C12	118.2 (6)
C9—N1—Zn1	130.2 (4)	C16—C11—C12	122.7 (6)
C1—N1—Zn1	108.7 (4)	O2—C12—C13	126.5 (6)
C19—N2—C11	123.5 (5)	O2—C12—C11	116.6 (6)
C19—N2—H2N	118.2	C13—C12—C11	116.8 (6)
C11—N2—H2N	118.2	C12—C13—C14	120.3 (6)
N1—C1—C6	122.0 (6)	C12—C13—H13	119.8
N1—C1—C2	116.4 (5)	C14—C13—H13	119.8
C6—C1—C2	121.6 (6)	C15—C14—C13	122.7 (6)
O1—C2—C3	123.0 (6)	C15—C14—H14	118.6
O1—C2—C1	118.7 (5)	C13—C14—H14	118.6
C3—C2—C1	118.3 (5)	C14—C15—C16	118.9 (5)
C2—C3—C4	120.1 (6)	C14—C15—H15	120.6
C2—C3—H3	119.9	C16—C15—H15	120.6
C4—C3—H3	119.9	C11—C16—C15	118.4 (6)
C5—C4—C3	122.8 (5)	C11—C16—C17	117.5 (6)
C5—C4—H4	118.6	C15—C16—C17	124.1 (5)
C3—C4—H4	118.6	C18—C17—C16	120.4 (5)
C4—C5—C6	118.3 (5)	C18—C17—H17	119.8
C4—C5—H5	120.9	C16—C17—H17	119.8
C6—C5—H5	120.9	C17—C18—C19	120.7 (6)
C1—C6—C7	116.7 (6)	C17—C18—H18	119.7
C1—C6—C5	119.0 (6)	C19—C18—H18	119.7
C7—C6—C5	124.3 (5)	N2—C19—C18	118.8 (6)
C8—C7—C6	120.5 (5)	N2—C19—C20	119.4 (5)
C8—C7—H7	119.8	C18—C19—C20	121.8 (6)
C6—C7—H7	119.8	C19—C20—H20A	109.5
C7—C8—C9	119.9 (6)	C19—C20—H20B	109.5
C7—C8—H8	120.1	H20A—C20—H20B	109.5
C9—C8—H8	120.1	C19—C20—H20C	109.5
N1—C9—C8	120.8 (6)	H20A—C20—H20C	109.5
N1—C9—C10	117.3 (5)	H20B—C20—H20C	109.5
N1—Zn1—O1—C2	15.2 (4)	C6—C7—C8—C9	2.2 (9)
I2—Zn1—O1—C2	136.8 (3)	C1—N1—C9—C8	−0.7 (9)
I1—Zn1—O1—C2	−87.7 (4)	Zn1—N1—C9—C8	166.6 (4)
O1—Zn1—N1—C9	175.6 (6)	C1—N1—C9—C10	176.5 (5)
I2—Zn1—N1—C9	59.0 (6)	Zn1—N1—C9—C10	−16.3 (9)
I1—Zn1—N1—C9	−74.1 (6)	C7—C8—C9—N1	−1.0 (9)
O1—Zn1—N1—C1	−15.9 (4)	C7—C8—C9—C10	−178.0 (6)
I2—Zn1—N1—C1	−132.6 (3)	C19—N2—C11—C16	−0.8 (8)
I1—Zn1—N1—C1	94.3 (4)	C19—N2—C11—C12	179.0 (6)
C9—N1—C1—C6	1.1 (9)	N2—C11—C12—O2	−2.6 (8)
Zn1—N1—C1—C6	−168.6 (5)	C16—C11—C12—O2	177.2 (5)
C9—N1—C1—C2	−176.1 (6)	N2—C11—C12—C13	177.6 (5)
Zn1—N1—C1—C2	14.1 (6)	C16—C11—C12—C13	−2.6 (9)
Zn1—O1—C2—C3	167.8 (5)	O2—C12—C13—C14	−178.9 (6)
Zn1—O1—C2—C1	−12.1 (6)	C11—C12—C13—C14	0.9 (9)
N1—C1—C2—O1	−1.7 (8)	C12—C13—C14—C15	1.3 (10)
C6—C1—C2—O1	−178.9 (6)	C13—C14—C15—C16	−1.7 (9)
N1—C1—C2—C3	178.3 (5)	N2—C11—C16—C15	−178.0 (5)
C6—C1—C2—C3	1.1 (9)	C12—C11—C16—C15	2.2 (9)
O1—C2—C3—C4	−179.8 (5)	N2—C11—C16—C17	1.4 (8)
C1—C2—C3—C4	0.2 (9)	C12—C11—C16—C17	−178.4 (6)
C2—C3—C4—C5	−0.6 (10)	C14—C15—C16—C11	0.0 (9)
C3—C4—C5—C6	−0.3 (9)	C14—C15—C16—C17	−179.4 (6)
N1—C1—C6—C7	0.1 (9)	C11—C16—C17—C18	−0.6 (9)
C2—C1—C6—C7	177.1 (5)	C15—C16—C17—C18	178.8 (6)
N1—C1—C6—C5	−179.1 (5)	C16—C17—C18—C19	−0.8 (9)
C2—C1—C6—C5	−2.0 (9)	C11—N2—C19—C18	−0.6 (9)
C4—C5—C6—C1	1.6 (9)	C11—N2—C19—C20	178.8 (6)
C4—C5—C6—C7	−177.5 (6)	C17—C18—C19—N2	1.4 (9)
C1—C6—C7—C8	−1.7 (9)	C17—C18—C19—C20	−178.0 (6)
C5—C6—C7—C8	177.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2o···O1	0.84	1.71	2.542 (6)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2o⋯O1	0.84	1.71	2.542 (6)	170