8-Hy-droxy-2-methyl-quinolinium dibromido(2-methyl-quinolin-8-olato-κN,O)zincate acetonitrile mono-solvate.

The reaction of 2-methyl-8-hy-droxy-quinoline and zinc bromide in acetonitrile affords the title solvated salt, (C(10)H(10)NO)[ZnBr(2)(C(10)H(8)NO)]·CH(3)CN, in which the Zn(II) ion is coordinated by a N,O-chelating 2-methyl-quinolin-8-olate ligand and two bromide ligands in a distorted tetra-hedral geometry. The cation is linked to the anion by an O-H⋯O hydrogen bond and the quinolinium H atom forms an inter-molecular N-H⋯N hydrogen bond with the acetonitrile solvent mol-ecule.

Related literature

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

Experimental

Crystal data

(C10H10NO)[ZnBr2(C10H8NO)]·C2H3N

M = 584.61

Triclinic,

a = 7.1870 (3) Å

b = 9.7795 (5) Å

c = 16.2520 (7) Å

α = 86.159 (4)°

β = 80.775 (4)°

γ = 85.098 (4)°

V = 1121.73 (9) Å3

Z = 2

Mo Kα radiation

μ = 4.68 mm−1

T = 100 K

0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.387, T max = 0.540

8710 measured reflections

4970 independent reflections

4197 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.065

S = 1.01

4970 reflections

282 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.86 e Å−3

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/S160053681103234X/lh5306sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103234X/lh5306Isup2.hkl

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

(C10H10NO)[ZnBr2(C10H8NO)]·C2H3N	Z = 2
Mr = 584.61	F(000) = 580
Triclinic, P1	Dx = 1.731 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1870 (3) Å	Cell parameters from 4618 reflections
b = 9.7795 (5) Å	θ = 2.4–29.1°
c = 16.2520 (7) Å	µ = 4.68 mm−1
α = 86.159 (4)°	T = 100 K
β = 80.775 (4)°	Block, yellow
γ = 85.098 (4)°	0.25 × 0.20 × 0.15 mm
V = 1121.73 (9) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	4970 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4197 reflections with I > 2σ(I)
Mirror	Rint = 0.033
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.5°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −9→12
Tmin = 0.387, Tmax = 0.540	l = −20→21
8710 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0183P)2] where P = (Fo2 + 2Fc2)/3
4970 reflections	(Δ/σ)max = 0.001
282 parameters	Δρmax = 0.54 e Å−3
2 restraints	Δρmin = −0.86 e Å−3

	x	y	z	Uiso*/Ueq
Br1	0.88168 (4)	0.83050 (3)	0.860009 (16)	0.02244 (8)
Br2	0.50073 (4)	0.95447 (3)	0.711001 (16)	0.02404 (8)
Zn1	0.61597 (4)	0.77959 (3)	0.800839 (17)	0.01579 (8)
O1	0.6552 (2)	0.59396 (18)	0.75476 (10)	0.0164 (4)
O2	0.7760 (2)	0.49663 (19)	0.61189 (10)	0.0180 (4)
H2	0.735 (4)	0.535 (3)	0.6565 (12)	0.051 (11)*
N1	0.4256 (3)	0.6890 (2)	0.88999 (12)	0.0138 (5)
N2	0.8330 (3)	0.3677 (2)	0.46831 (12)	0.0137 (5)
H1	0.853 (4)	0.323 (3)	0.5148 (10)	0.026 (8)*
N3	0.9248 (3)	0.1939 (2)	0.61350 (15)	0.0268 (6)
C1	0.4381 (3)	0.5504 (3)	0.87876 (14)	0.0135 (5)
C2	0.5632 (3)	0.5020 (3)	0.80728 (14)	0.0149 (5)
C3	0.5768 (4)	0.3633 (3)	0.79535 (15)	0.0173 (6)
H3	0.6582	0.3288	0.7481	0.021*
C4	0.4733 (4)	0.2716 (3)	0.85143 (15)	0.0182 (6)
H4	0.4860	0.1765	0.8411	0.022*
C5	0.3544 (3)	0.3161 (3)	0.92073 (16)	0.0187 (6)
H5	0.2857	0.2527	0.9581	0.022*
C6	0.3357 (3)	0.4576 (3)	0.93569 (15)	0.0156 (5)
C7	0.2193 (3)	0.5165 (3)	1.00595 (15)	0.0179 (6)
H7	0.1498	0.4591	1.0471	0.022*
C8	0.2076 (3)	0.6539 (3)	1.01421 (15)	0.0181 (6)
H8	0.1275	0.6922	1.0606	0.022*
C9	0.3124 (3)	0.7408 (3)	0.95511 (15)	0.0156 (6)
C10	0.3020 (4)	0.8932 (3)	0.96312 (16)	0.0222 (6)
H10A	0.4281	0.9263	0.9462	0.033*
H10B	0.2555	0.9144	1.0213	0.033*
H10C	0.2155	0.9387	0.9271	0.033*
C11	0.7546 (3)	0.5007 (3)	0.46969 (15)	0.0134 (5)
C12	0.7190 (3)	0.5680 (3)	0.54621 (15)	0.0143 (5)
C13	0.6326 (3)	0.6992 (3)	0.54599 (16)	0.0173 (6)
H13	0.6071	0.7463	0.5963	0.021*
C14	0.5817 (3)	0.7643 (3)	0.47216 (16)	0.0190 (6)
H14	0.5201	0.8542	0.4740	0.023*
C15	0.6185 (3)	0.7019 (3)	0.39779 (16)	0.0182 (6)
H15	0.5836	0.7480	0.3486	0.022*
C16	0.7093 (3)	0.5677 (3)	0.39514 (15)	0.0159 (6)
C17	0.7563 (3)	0.4941 (3)	0.32169 (16)	0.0202 (6)
H17	0.7326	0.5375	0.2699	0.024*
C18	0.8347 (3)	0.3626 (3)	0.32364 (16)	0.0200 (6)
H18	0.8650	0.3152	0.2735	0.024*
C19	0.8711 (3)	0.2964 (3)	0.39969 (16)	0.0173 (6)
C20	0.9466 (4)	0.1505 (3)	0.40586 (17)	0.0248 (6)
H20A	0.9691	0.1260	0.4631	0.037*
H20B	1.0657	0.1380	0.3673	0.037*
H20C	0.8548	0.0913	0.3913	0.037*
C21	0.9679 (4)	0.1787 (3)	0.67766 (18)	0.0220 (6)
C22	1.0230 (4)	0.1609 (3)	0.76012 (17)	0.0322 (7)
H22A	1.1477	0.1105	0.7564	0.048*
H22B	0.9301	0.1090	0.7976	0.048*
H22C	1.0285	0.2512	0.7820	0.048*

	U11	U22	U33	U12	U13	U23
Br1	0.02081 (15)	0.02701 (17)	0.02033 (14)	−0.00692 (12)	−0.00113 (11)	−0.00586 (12)
Br2	0.03621 (17)	0.01423 (15)	0.02002 (14)	0.00516 (12)	−0.00265 (12)	−0.00189 (11)
Zn1	0.01904 (16)	0.01350 (17)	0.01443 (15)	−0.00166 (13)	−0.00014 (12)	−0.00329 (12)
O1	0.0210 (9)	0.0138 (10)	0.0130 (8)	0.0004 (8)	0.0010 (7)	−0.0027 (7)
O2	0.0249 (10)	0.0167 (10)	0.0112 (9)	0.0011 (8)	−0.0001 (8)	−0.0020 (8)
N1	0.0138 (10)	0.0161 (12)	0.0120 (10)	−0.0006 (9)	−0.0024 (8)	−0.0043 (9)
N2	0.0137 (11)	0.0139 (12)	0.0126 (11)	−0.0010 (9)	0.0015 (9)	−0.0028 (9)
N3	0.0290 (14)	0.0192 (14)	0.0296 (14)	0.0031 (11)	0.0006 (11)	−0.0007 (11)
C1	0.0136 (12)	0.0148 (14)	0.0136 (12)	−0.0001 (10)	−0.0059 (10)	−0.0046 (10)
C2	0.0157 (13)	0.0187 (15)	0.0109 (12)	−0.0003 (11)	−0.0038 (10)	−0.0030 (11)
C3	0.0197 (13)	0.0191 (15)	0.0132 (12)	0.0042 (11)	−0.0033 (11)	−0.0065 (11)
C4	0.0245 (14)	0.0115 (14)	0.0210 (13)	−0.0003 (11)	−0.0106 (11)	−0.0032 (11)
C5	0.0190 (13)	0.0187 (15)	0.0202 (13)	−0.0052 (12)	−0.0068 (11)	0.0006 (11)
C6	0.0132 (12)	0.0201 (15)	0.0147 (12)	−0.0020 (11)	−0.0051 (10)	−0.0016 (11)
C7	0.0144 (13)	0.0252 (16)	0.0146 (12)	−0.0035 (12)	−0.0025 (10)	−0.0016 (11)
C8	0.0125 (12)	0.0279 (16)	0.0139 (12)	−0.0004 (12)	0.0000 (10)	−0.0067 (12)
C9	0.0143 (13)	0.0181 (15)	0.0160 (13)	−0.0004 (11)	−0.0059 (10)	−0.0061 (11)
C10	0.0224 (14)	0.0221 (16)	0.0225 (14)	0.0008 (12)	−0.0021 (12)	−0.0095 (12)
C11	0.0081 (12)	0.0136 (13)	0.0183 (13)	−0.0027 (10)	0.0001 (10)	−0.0015 (11)
C12	0.0125 (12)	0.0157 (14)	0.0139 (12)	−0.0042 (11)	0.0025 (10)	−0.0033 (11)
C13	0.0168 (13)	0.0160 (14)	0.0185 (13)	−0.0049 (11)	0.0028 (11)	−0.0051 (11)
C14	0.0153 (13)	0.0125 (14)	0.0279 (15)	0.0013 (11)	−0.0006 (11)	−0.0009 (11)
C15	0.0175 (13)	0.0172 (15)	0.0194 (13)	−0.0026 (11)	−0.0026 (11)	0.0034 (11)
C16	0.0113 (12)	0.0204 (15)	0.0162 (13)	−0.0028 (11)	−0.0007 (10)	−0.0030 (11)
C17	0.0175 (14)	0.0276 (17)	0.0162 (13)	−0.0050 (12)	−0.0024 (11)	−0.0033 (12)
C18	0.0181 (14)	0.0263 (16)	0.0161 (13)	−0.0008 (12)	0.0003 (11)	−0.0133 (12)
C19	0.0132 (13)	0.0177 (15)	0.0211 (14)	−0.0024 (11)	0.0005 (11)	−0.0066 (11)
C20	0.0282 (15)	0.0195 (16)	0.0263 (15)	0.0037 (13)	−0.0029 (12)	−0.0086 (12)
C21	0.0205 (14)	0.0115 (14)	0.0302 (16)	0.0020 (11)	0.0054 (13)	0.0000 (12)
C22	0.0312 (17)	0.036 (2)	0.0251 (15)	0.0058 (15)	0.0005 (13)	0.0072 (14)

Br1—Zn1	2.3738 (4)	C9—C10	1.500 (4)
Br2—Zn1	2.3566 (4)	C10—H10A	0.9800
Zn1—O1	1.9907 (18)	C10—H10B	0.9800
Zn1—N1	2.0386 (19)	C10—H10C	0.9800
O1—C2	1.339 (3)	C11—C16	1.409 (3)
O2—C12	1.336 (3)	C11—C12	1.423 (3)
O2—H2	0.837 (10)	C12—C13	1.377 (4)
N1—C9	1.328 (3)	C13—C14	1.406 (4)
N1—C1	1.373 (3)	C13—H13	0.9500
N2—C19	1.334 (3)	C14—C15	1.369 (4)
N2—C11	1.373 (3)	C14—H14	0.9500
N2—H1	0.875 (10)	C15—C16	1.415 (4)
N3—C21	1.131 (3)	C15—H15	0.9500
C1—C6	1.416 (3)	C16—C17	1.415 (4)
C1—C2	1.431 (3)	C17—C18	1.360 (4)
C2—C3	1.375 (4)	C17—H17	0.9500
C3—C4	1.406 (4)	C18—C19	1.408 (4)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.372 (3)	C19—C20	1.485 (4)
C4—H4	0.9500	C20—H20A	0.9800
C5—C6	1.412 (4)	C20—H20B	0.9800
C5—H5	0.9500	C20—H20C	0.9800
C6—C7	1.426 (3)	C21—C22	1.453 (4)
C7—C8	1.353 (4)	C22—H22A	0.9800
C7—H7	0.9500	C22—H22B	0.9800
C8—C9	1.407 (4)	C22—H22C	0.9800
C8—H8	0.9500
O1—Zn1—N1	83.97 (8)	C9—C10—H10C	109.5
O1—Zn1—Br2	114.56 (5)	H10A—C10—H10C	109.5
N1—Zn1—Br2	117.98 (6)	H10B—C10—H10C	109.5
O1—Zn1—Br1	111.06 (5)	N2—C11—C16	119.2 (2)
N1—Zn1—Br1	109.80 (6)	N2—C11—C12	119.6 (2)
Br2—Zn1—Br1	115.446 (16)	C16—C11—C12	121.2 (2)
C2—O1—Zn1	110.82 (14)	O2—C12—C13	126.2 (2)
C12—O2—H2	112 (2)	O2—C12—C11	115.8 (2)
C9—N1—C1	120.2 (2)	C13—C12—C11	118.0 (2)
C9—N1—Zn1	130.70 (18)	C12—C13—C14	120.8 (2)
C1—N1—Zn1	108.86 (15)	C12—C13—H13	119.6
C19—N2—C11	123.8 (2)	C14—C13—H13	119.6
C19—N2—H1	116.0 (19)	C15—C14—C13	121.8 (3)
C11—N2—H1	120.1 (19)	C15—C14—H14	119.1
N1—C1—C6	122.2 (2)	C13—C14—H14	119.1
N1—C1—C2	117.1 (2)	C14—C15—C16	119.1 (2)
C6—C1—C2	120.7 (2)	C14—C15—H15	120.4
O1—C2—C3	123.9 (2)	C16—C15—H15	120.4
O1—C2—C1	118.5 (2)	C11—C16—C17	117.0 (2)
C3—C2—C1	117.6 (2)	C11—C16—C15	119.0 (2)
C2—C3—C4	121.5 (2)	C17—C16—C15	124.0 (2)
C2—C3—H3	119.2	C18—C17—C16	121.4 (3)
C4—C3—H3	119.2	C18—C17—H17	119.3
C5—C4—C3	121.6 (3)	C16—C17—H17	119.3
C5—C4—H4	119.2	C17—C18—C19	120.2 (2)
C3—C4—H4	119.2	C17—C18—H18	119.9
C4—C5—C6	119.0 (2)	C19—C18—H18	119.9
C4—C5—H5	120.5	N2—C19—C18	118.2 (2)
C6—C5—H5	120.5	N2—C19—C20	119.5 (2)
C1—C6—C5	119.5 (2)	C18—C19—C20	122.3 (2)
C1—C6—C7	116.0 (2)	C19—C20—H20A	109.5
C5—C6—C7	124.5 (2)	C19—C20—H20B	109.5
C8—C7—C6	120.2 (2)	H20A—C20—H20B	109.5
C8—C7—H7	119.9	C19—C20—H20C	109.5
C6—C7—H7	119.9	H20A—C20—H20C	109.5
C7—C8—C9	121.0 (2)	H20B—C20—H20C	109.5
C7—C8—H8	119.5	N3—C21—C22	179.3 (3)
C9—C8—H8	119.5	C21—C22—H22A	109.5
N1—C9—C8	120.4 (2)	C21—C22—H22B	109.5
N1—C9—C10	117.7 (2)	H22A—C22—H22B	109.5
C8—C9—C10	121.9 (2)	C21—C22—H22C	109.5
C9—C10—H10A	109.5	H22A—C22—H22C	109.5
C9—C10—H10B	109.5	H22B—C22—H22C	109.5
H10A—C10—H10B	109.5
N1—Zn1—O1—C2	−7.93 (16)	C6—C7—C8—C9	−1.4 (4)
Br2—Zn1—O1—C2	−125.99 (14)	C1—N1—C9—C8	1.5 (3)
Br1—Zn1—O1—C2	101.00 (15)	Zn1—N1—C9—C8	−172.56 (17)
O1—Zn1—N1—C9	−178.6 (2)	C1—N1—C9—C10	−178.9 (2)
Br2—Zn1—N1—C9	−64.0 (2)	Zn1—N1—C9—C10	7.1 (3)
Br1—Zn1—N1—C9	71.1 (2)	C7—C8—C9—N1	−0.2 (4)
O1—Zn1—N1—C1	6.82 (15)	C7—C8—C9—C10	−179.8 (2)
Br2—Zn1—N1—C1	121.47 (14)	C19—N2—C11—C16	0.4 (4)
Br1—Zn1—N1—C1	−103.42 (15)	C19—N2—C11—C12	179.9 (2)
C9—N1—C1—C6	−1.1 (4)	N2—C11—C12—O2	3.6 (3)
Zn1—N1—C1—C6	174.10 (19)	C16—C11—C12—O2	−176.9 (2)
C9—N1—C1—C2	−179.9 (2)	N2—C11—C12—C13	−177.2 (2)
Zn1—N1—C1—C2	−4.7 (3)	C16—C11—C12—C13	2.2 (3)
Zn1—O1—C2—C3	−174.4 (2)	O2—C12—C13—C14	179.0 (2)
Zn1—O1—C2—C1	7.7 (3)	C11—C12—C13—C14	−0.1 (4)
N1—C1—C2—O1	−2.0 (3)	C12—C13—C14—C15	−1.2 (4)
C6—C1—C2—O1	179.2 (2)	C13—C14—C15—C16	0.4 (4)
N1—C1—C2—C3	−180.0 (2)	N2—C11—C16—C17	−2.8 (3)
C6—C1—C2—C3	1.2 (4)	C12—C11—C16—C17	177.8 (2)
O1—C2—C3—C4	−178.4 (2)	N2—C11—C16—C15	176.4 (2)
C1—C2—C3—C4	−0.5 (4)	C12—C11—C16—C15	−3.1 (3)
C2—C3—C4—C5	−0.2 (4)	C14—C15—C16—C11	1.7 (4)
C3—C4—C5—C6	0.2 (4)	C14—C15—C16—C17	−179.2 (2)
N1—C1—C6—C5	180.0 (2)	C11—C16—C17—C18	2.6 (4)
C2—C1—C6—C5	−1.3 (4)	C15—C16—C17—C18	−176.5 (2)
N1—C1—C6—C7	−0.5 (3)	C16—C17—C18—C19	0.0 (4)
C2—C1—C6—C7	178.3 (2)	C11—N2—C19—C18	2.2 (4)
C4—C5—C6—C1	0.6 (4)	C11—N2—C19—C20	−176.8 (2)
C4—C5—C6—C7	−179.0 (2)	C17—C18—C19—N2	−2.3 (4)
C1—C6—C7—C8	1.7 (4)	C17—C18—C19—C20	176.6 (2)
C5—C6—C7—C8	−178.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.84 (1)	1.73 (1)	2.561 (2)	173 (4)
N2—H1···N3	0.88 (1)	2.08 (1)	2.943 (3)	171 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.84 (1)	1.73 (1)	2.561 (2)	173 (4)
N2—H1⋯N3	0.88 (1)	2.08 (1)	2.943 (3)	171 (3)