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

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

Related literature

For related structures, see: Najafi et al. (2010a ▶,b ▶); Sattarzadeh et al. (2009 ▶).

Experimental

Crystal data

(an class="Chemical">C10H10NO)[Zn(C10H8NO)Cl2]·2C2H3N

M = 536.74

Monoclinic,

a = 9.9913 (2) Å

b = 23.1642 (5) Å

c = 10.4317 (2) Å

β = 95.687 (2)°

V = 2402.43 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.27 mm−1

T = 100 K

0.35 × 0.30 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with n class="Chemical">an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.664, T max = 0.741

11981 measured reflections

5349 independent reflections

4576 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.070

S = 1.04

5349 reflections

310 parameters

2 restraints

an class="Disease">H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.38 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/S1600536811032338/lh5305sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032338/lh5305Isup2.hkl

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

(C10H10NO)[Zn(C10H8NO)Cl2]·2C2H3N	F(000) = 1104
Mr = 536.74	Dx = 1.484 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6293 reflections
a = 9.9913 (2) Å	θ = 2.6–27.5°
b = 23.1642 (5) Å	µ = 1.27 mm−1
c = 10.4317 (2) Å	T = 100 K
β = 95.687 (2)°	Block, yellow
V = 2402.43 (8) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	5349 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4576 reflections with I > 2σ(I)
Mirror	Rint = 0.026
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.6°
ω scans	h = −10→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −19→30
Tmin = 0.664, Tmax = 0.741	l = −13→12
11981 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0274P)2 + 0.9529P] where P = (Fo2 + 2Fc2)/3
5349 reflections	(Δ/σ)max = 0.001
310 parameters	Δρmax = 0.38 e Å−3
2 restraints	Δρmin = −0.38 e Å−3

	x	y	z	Uiso*/Ueq
Zn1	0.50594 (2)	0.616546 (9)	0.82369 (2)	0.01365 (7)
Cl1	0.29181 (4)	0.60211 (2)	0.86105 (4)	0.02035 (11)
Cl2	0.59332 (5)	0.54481 (2)	0.71722 (5)	0.02002 (11)
O1	0.52662 (12)	0.69544 (5)	0.75329 (12)	0.0166 (3)
O2	0.52356 (13)	0.74218 (6)	0.53126 (12)	0.0183 (3)
N1	0.62045 (14)	0.64878 (7)	0.98072 (14)	0.0129 (3)
N2	0.43930 (15)	0.79211 (7)	0.30728 (15)	0.0147 (3)
N3	0.48880 (18)	0.88039 (8)	0.51544 (17)	0.0257 (4)
N4	0.4352 (2)	0.95235 (9)	0.86812 (19)	0.0363 (5)
C1	0.62800 (17)	0.70784 (8)	0.96775 (17)	0.0134 (4)
C2	0.57490 (17)	0.73143 (8)	0.84652 (17)	0.0137 (4)
C3	0.57620 (17)	0.79080 (8)	0.83285 (18)	0.0160 (4)
H3	0.5408	0.8078	0.7538	0.019*
C4	0.62944 (18)	0.82644 (8)	0.93482 (19)	0.0186 (4)
H4	0.6277	0.8671	0.9234	0.022*
C5	0.68383 (17)	0.80403 (8)	1.05027 (18)	0.0169 (4)
H5	0.7204	0.8289	1.1173	0.020*
C6	0.68473 (17)	0.74367 (8)	1.06793 (17)	0.0145 (4)
C7	0.73945 (17)	0.71553 (9)	1.18220 (18)	0.0176 (4)
H7	0.7802	0.7376	1.2522	0.021*
C8	0.73379 (18)	0.65707 (9)	1.19184 (18)	0.0178 (4)
H8	0.7720	0.6385	1.2680	0.021*
C9	0.67119 (17)	0.62375 (8)	1.08874 (18)	0.0151 (4)
C10	0.6608 (2)	0.55949 (8)	1.09901 (18)	0.0201 (4)
H10A	0.6233	0.5436	1.0161	0.030*
H10B	0.6019	0.5496	1.1655	0.030*
H10C	0.7504	0.5432	1.1222	0.030*
C11	0.43571 (17)	0.73305 (8)	0.31627 (17)	0.0143 (4)
C12	0.48188 (17)	0.70639 (8)	0.43413 (17)	0.0151 (4)
C13	0.48303 (19)	0.64703 (8)	0.43976 (18)	0.0194 (4)
H13	0.5167	0.6281	0.5171	0.023*
C14	0.4344 (2)	0.61412 (9)	0.33107 (19)	0.0219 (4)
H14	0.4348	0.5732	0.3370	0.026*
C15	0.38685 (19)	0.63977 (9)	0.21745 (19)	0.0206 (4)
H15	0.3539	0.6168	0.1456	0.025*
C16	0.38707 (17)	0.70040 (8)	0.20771 (17)	0.0165 (4)
C17	0.34114 (18)	0.73119 (9)	0.09457 (18)	0.0198 (4)
H17	0.3041	0.7107	0.0205	0.024*
C18	0.34947 (18)	0.78995 (9)	0.09070 (18)	0.0203 (4)
H18	0.3197	0.8099	0.0135	0.024*
C19	0.40153 (18)	0.82124 (9)	0.19951 (18)	0.0180 (4)
C20	0.4180 (2)	0.88510 (9)	0.1995 (2)	0.0242 (4)
H20A	0.4989	0.8957	0.2554	0.036*
H20B	0.3392	0.9032	0.2316	0.036*
H20C	0.4267	0.8984	0.1116	0.036*
C21	0.54598 (19)	0.91734 (9)	0.56751 (19)	0.0209 (4)
C22	0.6214 (2)	0.96503 (9)	0.6311 (2)	0.0286 (5)
H22A	0.6586	0.9530	0.7174	0.043*
H22B	0.5614	0.9981	0.6381	0.043*
H22C	0.6949	0.9761	0.5804	0.043*
C23	0.3541 (2)	0.98177 (9)	0.90117 (19)	0.0235 (4)
C24	0.2502 (2)	1.01887 (10)	0.9443 (2)	0.0283 (5)
H24A	0.1619	1.0059	0.9057	0.042*
H24B	0.2656	1.0587	0.9180	0.042*
H24C	0.2531	1.0170	1.0384	0.042*
H1	0.463 (2)	0.8111 (10)	0.3782 (15)	0.041 (7)*
H2	0.528 (3)	0.7256 (11)	0.6035 (15)	0.050 (8)*

	U11	U22	U33	U12	U13	U23
Zn1	0.01575 (11)	0.01283 (11)	0.01221 (11)	−0.00044 (8)	0.00062 (8)	−0.00073 (8)
Cl1	0.0171 (2)	0.0268 (3)	0.0173 (2)	−0.00230 (19)	0.00304 (18)	−0.0017 (2)
Cl2	0.0212 (2)	0.0164 (2)	0.0227 (2)	0.00204 (18)	0.00295 (19)	−0.00457 (19)
O1	0.0234 (7)	0.0148 (7)	0.0112 (6)	−0.0032 (5)	−0.0013 (5)	−0.0007 (5)
O2	0.0248 (7)	0.0178 (7)	0.0116 (7)	−0.0021 (6)	−0.0013 (6)	0.0010 (6)
N1	0.0124 (7)	0.0145 (8)	0.0118 (7)	0.0016 (6)	0.0011 (6)	0.0007 (6)
N2	0.0151 (7)	0.0165 (8)	0.0125 (8)	0.0017 (6)	0.0013 (6)	−0.0015 (7)
N3	0.0297 (9)	0.0237 (10)	0.0245 (9)	−0.0034 (8)	0.0065 (8)	−0.0017 (8)
N4	0.0380 (11)	0.0362 (12)	0.0327 (11)	0.0087 (9)	−0.0070 (9)	−0.0074 (9)
C1	0.0113 (8)	0.0146 (9)	0.0147 (9)	0.0002 (7)	0.0036 (7)	−0.0016 (7)
C2	0.0127 (8)	0.0152 (9)	0.0136 (9)	0.0003 (7)	0.0030 (7)	−0.0001 (7)
C3	0.0148 (8)	0.0162 (9)	0.0170 (9)	−0.0001 (7)	0.0016 (7)	0.0033 (8)
C4	0.0178 (9)	0.0131 (9)	0.0252 (10)	−0.0010 (7)	0.0042 (8)	−0.0019 (8)
C5	0.0140 (8)	0.0166 (9)	0.0199 (10)	−0.0025 (7)	0.0006 (8)	−0.0046 (8)
C6	0.0102 (8)	0.0181 (9)	0.0153 (9)	−0.0020 (7)	0.0020 (7)	−0.0031 (8)
C7	0.0142 (8)	0.0238 (10)	0.0143 (9)	−0.0012 (8)	−0.0009 (7)	−0.0049 (8)
C8	0.0165 (9)	0.0231 (10)	0.0132 (9)	0.0029 (8)	−0.0015 (7)	0.0022 (8)
C9	0.0126 (8)	0.0169 (9)	0.0158 (9)	0.0021 (7)	0.0020 (7)	0.0001 (8)
C10	0.0249 (10)	0.0192 (10)	0.0158 (9)	0.0025 (8)	−0.0005 (8)	0.0033 (8)
C11	0.0119 (8)	0.0154 (9)	0.0162 (9)	−0.0007 (7)	0.0043 (7)	−0.0016 (8)
C12	0.0137 (8)	0.0189 (10)	0.0132 (9)	−0.0001 (7)	0.0035 (7)	−0.0016 (8)
C13	0.0226 (9)	0.0195 (10)	0.0171 (9)	0.0019 (8)	0.0075 (8)	0.0027 (8)
C14	0.0262 (10)	0.0159 (10)	0.0256 (11)	−0.0026 (8)	0.0121 (9)	−0.0042 (8)
C15	0.0218 (10)	0.0217 (10)	0.0194 (10)	−0.0056 (8)	0.0076 (8)	−0.0079 (9)
C16	0.0129 (8)	0.0219 (10)	0.0153 (9)	−0.0020 (7)	0.0047 (7)	−0.0039 (8)
C17	0.0136 (9)	0.0319 (12)	0.0140 (9)	0.0006 (8)	0.0016 (7)	−0.0058 (8)
C18	0.0168 (9)	0.0300 (11)	0.0140 (9)	0.0058 (8)	0.0010 (8)	0.0025 (8)
C19	0.0141 (8)	0.0235 (10)	0.0165 (9)	0.0055 (8)	0.0027 (7)	0.0017 (8)
C20	0.0289 (11)	0.0211 (11)	0.0227 (11)	0.0063 (9)	0.0034 (9)	0.0043 (9)
C21	0.0220 (10)	0.0218 (11)	0.0198 (10)	0.0029 (9)	0.0067 (8)	0.0030 (9)
C22	0.0331 (11)	0.0223 (11)	0.0300 (11)	−0.0030 (9)	0.0008 (10)	−0.0029 (9)
C23	0.0268 (10)	0.0249 (11)	0.0169 (10)	−0.0051 (9)	−0.0066 (8)	0.0021 (9)
C24	0.0300 (11)	0.0302 (12)	0.0249 (11)	0.0025 (9)	0.0034 (9)	0.0028 (10)

Zn1—O1	1.9880 (13)	C10—H10A	0.9800
Zn1—N1	2.0441 (15)	C10—H10B	0.9800
Zn1—Cl2	2.2246 (5)	C10—H10C	0.9800
Zn1—Cl1	2.2375 (5)	C11—C16	1.408 (3)
O1—C2	1.334 (2)	C11—C12	1.412 (3)
O2—C12	1.343 (2)	C12—C13	1.376 (3)
O2—H2	0.843 (10)	C13—C14	1.412 (3)
N1—C9	1.323 (2)	C13—H13	0.9500
N1—C1	1.378 (2)	C14—C15	1.368 (3)
N2—C19	1.333 (2)	C14—H14	0.9500
N2—C11	1.372 (2)	C15—C16	1.408 (3)
N2—H1	0.874 (10)	C15—H15	0.9500
N3—C21	1.137 (3)	C16—C17	1.416 (3)
N4—C23	1.138 (3)	C17—C18	1.365 (3)
C1—C6	1.409 (2)	C17—H17	0.9500
C1—C2	1.431 (2)	C18—C19	1.403 (3)
C2—C3	1.383 (3)	C18—H18	0.9500
C3—C4	1.408 (3)	C19—C20	1.488 (3)
C3—H3	0.9500	C20—H20A	0.9800
C4—C5	1.373 (3)	C20—H20B	0.9800
C4—H4	0.9500	C20—H20C	0.9800
C5—C6	1.410 (3)	C21—C22	1.459 (3)
C5—H5	0.9500	C22—H22A	0.9800
C6—C7	1.420 (3)	C22—H22B	0.9800
C7—C8	1.360 (3)	C22—H22C	0.9800
C7—H7	0.9500	C23—C24	1.453 (3)
C8—C9	1.418 (3)	C24—H24A	0.9800
C8—H8	0.9500	C24—H24B	0.9800
C9—C10	1.497 (3)	C24—H24C	0.9800
O1—Zn1—N1	83.67 (6)	N2—C11—C16	119.35 (17)
O1—Zn1—Cl2	116.23 (4)	N2—C11—C12	119.16 (16)
N1—Zn1—Cl2	117.18 (4)	C16—C11—C12	121.50 (17)
O1—Zn1—Cl1	109.75 (4)	O2—C12—C13	125.73 (17)
N1—Zn1—Cl1	112.58 (4)	O2—C12—C11	115.91 (16)
Cl2—Zn1—Cl1	113.870 (19)	C13—C12—C11	118.34 (17)
C2—O1—Zn1	110.39 (11)	C12—C13—C14	120.30 (18)
C12—O2—H2	112.2 (19)	C12—C13—H13	119.9
C9—N1—C1	119.93 (16)	C14—C13—H13	119.9
C9—N1—Zn1	131.25 (13)	C15—C14—C13	121.57 (18)
C1—N1—Zn1	108.42 (11)	C15—C14—H14	119.2
C19—N2—C11	123.72 (17)	C13—C14—H14	119.2
C19—N2—H1	119.3 (17)	C14—C15—C16	119.51 (18)
C11—N2—H1	116.9 (17)	C14—C15—H15	120.2
N1—C1—C6	122.28 (16)	C16—C15—H15	120.2
N1—C1—C2	116.55 (16)	C11—C16—C15	118.74 (17)
C6—C1—C2	121.17 (17)	C11—C16—C17	117.22 (17)
O1—C2—C3	123.55 (17)	C15—C16—C17	124.04 (18)
O1—C2—C1	118.77 (16)	C18—C17—C16	120.76 (18)
C3—C2—C1	117.68 (17)	C18—C17—H17	119.6
C2—C3—C4	120.78 (17)	C16—C17—H17	119.6
C2—C3—H3	119.6	C17—C18—C19	120.69 (18)
C4—C3—H3	119.6	C17—C18—H18	119.7
C5—C4—C3	121.86 (18)	C19—C18—H18	119.7
C5—C4—H4	119.1	N2—C19—C18	118.17 (18)
C3—C4—H4	119.1	N2—C19—C20	118.75 (17)
C4—C5—C6	119.09 (17)	C18—C19—C20	123.07 (18)
C4—C5—H5	120.5	C19—C20—H20A	109.5
C6—C5—H5	120.5	C19—C20—H20B	109.5
C1—C6—C5	119.36 (17)	H20A—C20—H20B	109.5
C1—C6—C7	116.46 (17)	C19—C20—H20C	109.5
C5—C6—C7	124.18 (17)	H20A—C20—H20C	109.5
C8—C7—C6	120.27 (17)	H20B—C20—H20C	109.5
C8—C7—H7	119.9	N3—C21—C22	178.3 (2)
C6—C7—H7	119.9	C21—C22—H22A	109.5
C7—C8—C9	120.30 (18)	C21—C22—H22B	109.5
C7—C8—H8	119.8	H22A—C22—H22B	109.5
C9—C8—H8	119.8	C21—C22—H22C	109.5
N1—C9—C8	120.70 (17)	H22A—C22—H22C	109.5
N1—C9—C10	118.26 (16)	H22B—C22—H22C	109.5
C8—C9—C10	121.04 (17)	N4—C23—C24	179.4 (3)
C9—C10—H10A	109.5	C23—C24—H24A	109.5
C9—C10—H10B	109.5	C23—C24—H24B	109.5
H10A—C10—H10B	109.5	H24A—C24—H24B	109.5
C9—C10—H10C	109.5	C23—C24—H24C	109.5
H10A—C10—H10C	109.5	H24A—C24—H24C	109.5
H10B—C10—H10C	109.5	H24B—C24—H24C	109.5
N1—Zn1—O1—C2	−13.18 (11)	C6—C7—C8—C9	−1.1 (3)
Cl2—Zn1—O1—C2	−130.42 (10)	C1—N1—C9—C8	−0.1 (2)
Cl1—Zn1—O1—C2	98.57 (10)	Zn1—N1—C9—C8	−171.82 (12)
O1—Zn1—N1—C9	−175.78 (16)	C1—N1—C9—C10	179.93 (15)
Cl2—Zn1—N1—C9	−59.49 (16)	Zn1—N1—C9—C10	8.2 (2)
Cl1—Zn1—N1—C9	75.43 (15)	C7—C8—C9—N1	1.7 (3)
O1—Zn1—N1—C1	11.78 (11)	C7—C8—C9—C10	−178.36 (17)
Cl2—Zn1—N1—C1	128.07 (10)	C19—N2—C11—C16	−1.4 (3)
Cl1—Zn1—N1—C1	−97.01 (10)	C19—N2—C11—C12	178.10 (16)
C9—N1—C1—C6	−2.1 (2)	N2—C11—C12—O2	1.6 (2)
Zn1—N1—C1—C6	171.36 (13)	C16—C11—C12—O2	−178.84 (15)
C9—N1—C1—C2	177.96 (15)	N2—C11—C12—C13	−177.21 (16)
Zn1—N1—C1—C2	−8.60 (17)	C16—C11—C12—C13	2.3 (3)
Zn1—O1—C2—C3	−167.34 (14)	O2—C12—C13—C14	179.05 (16)
Zn1—O1—C2—C1	12.42 (18)	C11—C12—C13—C14	−2.2 (3)
N1—C1—C2—O1	−2.4 (2)	C12—C13—C14—C15	0.9 (3)
C6—C1—C2—O1	177.65 (15)	C13—C14—C15—C16	0.5 (3)
N1—C1—C2—C3	177.38 (15)	N2—C11—C16—C15	178.55 (16)
C6—C1—C2—C3	−2.6 (2)	C12—C11—C16—C15	−1.0 (2)
O1—C2—C3—C4	−179.59 (16)	N2—C11—C16—C17	−1.4 (2)
C1—C2—C3—C4	0.6 (2)	C12—C11—C16—C17	179.06 (15)
C2—C3—C4—C5	1.1 (3)	C14—C15—C16—C11	−0.4 (3)
C3—C4—C5—C6	−0.9 (3)	C14—C15—C16—C17	179.50 (17)
N1—C1—C6—C5	−177.17 (16)	C11—C16—C17—C18	2.6 (2)
C2—C1—C6—C5	2.8 (2)	C15—C16—C17—C18	−177.32 (17)
N1—C1—C6—C7	2.6 (2)	C16—C17—C18—C19	−1.1 (3)
C2—C1—C6—C7	−177.46 (15)	C11—N2—C19—C18	3.0 (2)
C4—C5—C6—C1	−1.0 (3)	C11—N2—C19—C20	−176.26 (16)
C4—C5—C6—C7	179.25 (16)	C17—C18—C19—N2	−1.7 (3)
C1—C6—C7—C8	−1.0 (2)	C17—C18—C19—C20	177.56 (17)
C5—C6—C7—C8	178.77 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···N3	0.87 (1)	2.15 (1)	2.988 (2)	161 (2)
O2—H2···O1	0.84 (1)	1.71 (1)	2.554 (2)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯N3	0.87 (1)	2.15 (1)	2.988 (2)	161 (2)
O2—H2⋯O1	0.84 (1)	1.71 (1)	2.554 (2)	176 (3)