Chlorido(8-hy-droxy-quinoline-κN,O)(quinolin-8-olato-κN,O)zinc methanol monosolvate.

In the title compound, [Zn(C(9)H(6)NO)Cl(C(9)H(7)NO)]·CH(3)OH, the Zn(II) ion is N,O-chelated by both a neutral and a deprotonated quinolin-8-ol ligand, with a chloride ligand in the apical site completing the square-pyramidal coordination geometry. The Zn(II) ion is displaced by 0.586 Å in the direction of the chloride ligand from the atoms forming the square plane. In the crystal, the components are linked by inter-molecular O-H⋯O hydrogen bonds, generating chains along the b axis.

Related literature

For the crystal structure of 8-hy­droxy-2-methyl­quinolinium dichlorido(2-methyl­quinolin-8-olato-κ 2 N,O)zincate(II) aceto­nitrile disolvate, see: Najafi et al. (2011 ▶).

Experimental

Crystal data

[Zn(C9H6NO)Cl(C9H7NO)]·CH4O

M = 422.17

Triclinic,

a = 8.4110 (4) Å

b = 8.4692 (4) Å

c = 13.2667 (7) Å

α = 99.905 (4)°

β = 95.341 (4)°

γ = 110.549 (5)°

V = 859.58 (7) Å3

Z = 2

Mo Kα radiation

μ = 1.61 mm−1

T = 100 K

0.15 × 0.15 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.795, T max = 0.795

6878 measured reflections

3806 independent reflections

3258 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.082

S = 1.05

3806 reflections

244 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.42 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/S160053681103337X/lh5311sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103337X/lh5311Isup2.hkl

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

[Zn(C9H6NO)Cl(C9H7NO)]·CH4O	Z = 2
Mr = 422.17	F(000) = 432
Triclinic, P1	Dx = 1.631 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4110 (4) Å	Cell parameters from 3680 reflections
b = 8.4692 (4) Å	θ = 2.6–29.3°
c = 13.2667 (7) Å	µ = 1.61 mm−1
α = 99.905 (4)°	T = 100 K
β = 95.341 (4)°	Cuboid, yellow
γ = 110.549 (5)°	0.15 × 0.15 × 0.15 mm
V = 859.58 (7) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	3806 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3258 reflections with I > 2σ(I)
Mirror	Rint = 0.045
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.6°
ω scans	h = −8→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −10→10
Tmin = 0.795, Tmax = 0.795	l = −17→17
6878 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0336P)2 + 0.2331P] where P = (Fo2 + 2Fc2)/3
3806 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.47 e Å−3
2 restraints	Δρmin = −0.42 e Å−3

	x	y	z	Uiso*/Ueq
Zn1	0.64683 (4)	0.45465 (3)	0.717891 (19)	0.01236 (9)
Cl1	0.91659 (8)	0.57790 (8)	0.80776 (4)	0.01774 (14)
O1	0.5263 (2)	0.2082 (2)	0.73472 (12)	0.0148 (4)
O2	0.6496 (2)	0.6842 (2)	0.64293 (12)	0.0156 (4)
O3	0.6795 (2)	0.9898 (2)	0.72616 (12)	0.0196 (4)
N1	0.4816 (3)	0.5009 (2)	0.81134 (14)	0.0121 (4)
N2	0.6744 (3)	0.3866 (2)	0.56612 (14)	0.0121 (4)
C1	0.3948 (3)	0.3574 (3)	0.84634 (16)	0.0118 (5)
C2	0.4213 (3)	0.2018 (3)	0.80397 (16)	0.0123 (5)
C3	0.3344 (3)	0.0553 (3)	0.83838 (17)	0.0153 (5)
H3A	0.3474	−0.0499	0.8109	0.018*
C4	0.2270 (3)	0.0585 (3)	0.91326 (17)	0.0163 (5)
H4	0.1689	−0.0450	0.9350	0.020*
C5	0.2039 (3)	0.2065 (3)	0.95567 (17)	0.0157 (5)
H5	0.1328	0.2064	1.0073	0.019*
C6	0.2873 (3)	0.3594 (3)	0.92149 (17)	0.0131 (5)
C7	0.2700 (3)	0.5192 (3)	0.95927 (17)	0.0143 (5)
H7	0.1977	0.5269	1.0093	0.017*
C8	0.3578 (3)	0.6616 (3)	0.92317 (17)	0.0149 (5)
H8	0.3470	0.7689	0.9481	0.018*
C9	0.4638 (3)	0.6488 (3)	0.84925 (17)	0.0142 (5)
H9	0.5250	0.7490	0.8253	0.017*
C10	0.7339 (3)	0.5164 (3)	0.51453 (16)	0.0121 (5)
C11	0.7243 (3)	0.6787 (3)	0.55646 (17)	0.0131 (5)
C12	0.7850 (3)	0.8125 (3)	0.50826 (18)	0.0159 (5)
H12	0.7808	0.9216	0.5368	0.019*
C13	0.8537 (3)	0.7903 (3)	0.41679 (18)	0.0163 (5)
H13	0.8946	0.8849	0.3841	0.020*
C14	0.8633 (3)	0.6356 (3)	0.37360 (17)	0.0149 (5)
H14	0.9110	0.6233	0.3119	0.018*
C15	0.8012 (3)	0.4946 (3)	0.42191 (17)	0.0130 (5)
C16	0.7985 (3)	0.3275 (3)	0.38085 (17)	0.0150 (5)
H16	0.8439	0.3067	0.3192	0.018*
C17	0.7302 (3)	0.1966 (3)	0.43052 (17)	0.0167 (5)
H17	0.7224	0.0829	0.4017	0.020*
C18	0.6719 (3)	0.2314 (3)	0.52412 (17)	0.0146 (5)
H18	0.6287	0.1402	0.5591	0.018*
C19	0.8321 (4)	1.0712 (3)	0.8018 (2)	0.0255 (6)
H19A	0.8904	1.1906	0.7952	0.038*
H19B	0.9090	1.0079	0.7907	0.038*
H19C	0.8020	1.0711	0.8714	0.038*
H2	0.653 (4)	0.785 (2)	0.664 (2)	0.033 (9)*
H3	0.626 (4)	1.056 (4)	0.727 (2)	0.040 (10)*

	U11	U22	U33	U12	U13	U23
Zn1	0.01352 (17)	0.01182 (15)	0.01295 (15)	0.00472 (12)	0.00608 (11)	0.00385 (11)
Cl1	0.0132 (3)	0.0223 (3)	0.0164 (3)	0.0050 (3)	0.0049 (2)	0.0030 (2)
O1	0.0179 (10)	0.0128 (8)	0.0163 (8)	0.0067 (7)	0.0085 (7)	0.0049 (7)
O2	0.0220 (10)	0.0138 (9)	0.0148 (8)	0.0091 (8)	0.0096 (7)	0.0039 (7)
O3	0.0210 (11)	0.0166 (9)	0.0222 (9)	0.0101 (8)	0.0017 (8)	0.0016 (7)
N1	0.0120 (11)	0.0112 (9)	0.0134 (9)	0.0046 (8)	0.0023 (8)	0.0029 (8)
N2	0.0129 (11)	0.0119 (9)	0.0136 (9)	0.0057 (9)	0.0040 (8)	0.0049 (8)
C1	0.0091 (12)	0.0139 (11)	0.0117 (10)	0.0029 (10)	0.0005 (9)	0.0046 (9)
C2	0.0127 (12)	0.0127 (11)	0.0114 (11)	0.0046 (10)	0.0023 (9)	0.0031 (9)
C3	0.0161 (13)	0.0126 (11)	0.0159 (12)	0.0042 (10)	0.0034 (10)	0.0023 (9)
C4	0.0154 (13)	0.0160 (12)	0.0156 (12)	0.0016 (10)	0.0028 (10)	0.0072 (10)
C5	0.0120 (13)	0.0191 (12)	0.0155 (11)	0.0038 (10)	0.0055 (9)	0.0049 (10)
C6	0.0092 (12)	0.0158 (12)	0.0130 (11)	0.0032 (10)	0.0015 (9)	0.0033 (9)
C7	0.0147 (13)	0.0186 (12)	0.0121 (11)	0.0079 (11)	0.0053 (9)	0.0044 (9)
C8	0.0174 (14)	0.0145 (12)	0.0158 (11)	0.0094 (11)	0.0044 (10)	0.0025 (9)
C9	0.0148 (13)	0.0136 (11)	0.0153 (11)	0.0057 (10)	0.0031 (10)	0.0048 (9)
C10	0.0125 (13)	0.0101 (11)	0.0132 (11)	0.0033 (10)	0.0015 (9)	0.0037 (9)
C11	0.0110 (12)	0.0148 (11)	0.0154 (11)	0.0058 (10)	0.0037 (9)	0.0049 (9)
C12	0.0158 (13)	0.0128 (12)	0.0193 (12)	0.0063 (10)	0.0030 (10)	0.0022 (10)
C13	0.0164 (14)	0.0152 (12)	0.0180 (12)	0.0038 (11)	0.0049 (10)	0.0089 (10)
C14	0.0153 (13)	0.0180 (12)	0.0119 (11)	0.0050 (11)	0.0042 (9)	0.0061 (9)
C15	0.0112 (12)	0.0145 (11)	0.0120 (11)	0.0039 (10)	0.0006 (9)	0.0025 (9)
C16	0.0167 (13)	0.0166 (12)	0.0118 (11)	0.0061 (11)	0.0040 (9)	0.0028 (9)
C17	0.0203 (14)	0.0120 (11)	0.0174 (12)	0.0070 (11)	0.0049 (10)	−0.0008 (9)
C18	0.0157 (13)	0.0122 (11)	0.0153 (11)	0.0038 (10)	0.0037 (9)	0.0038 (9)
C19	0.0260 (16)	0.0225 (14)	0.0262 (14)	0.0086 (13)	0.0004 (12)	0.0042 (11)

Zn1—O1	2.0377 (16)	C7—C8	1.367 (3)
Zn1—N1	2.0392 (18)	C7—H7	0.9500
Zn1—N2	2.0547 (17)	C8—C9	1.401 (3)
Zn1—Cl1	2.2505 (7)	C8—H8	0.9500
Zn1—O2	2.3257 (16)	C9—H9	0.9500
O1—C2	1.327 (3)	C10—C15	1.410 (3)
O2—C11	1.360 (3)	C10—C11	1.424 (3)
O2—H2	0.842 (10)	C11—C12	1.363 (3)
O3—C19	1.425 (3)	C12—C13	1.404 (3)
O3—H3	0.836 (10)	C12—H12	0.9500
N1—C9	1.332 (3)	C13—C14	1.369 (3)
N1—C1	1.364 (3)	C13—H13	0.9500
N2—C18	1.328 (3)	C14—C15	1.414 (3)
N2—C10	1.366 (3)	C14—H14	0.9500
C1—C6	1.409 (3)	C15—C16	1.417 (3)
C1—C2	1.441 (3)	C16—C17	1.367 (3)
C2—C3	1.379 (3)	C16—H16	0.9500
C3—C4	1.407 (3)	C17—C18	1.399 (3)
C3—H3A	0.9500	C17—H17	0.9500
C4—C5	1.369 (3)	C18—H18	0.9500
C4—H4	0.9500	C19—H19A	0.9800
C5—C6	1.414 (3)	C19—H19B	0.9800
C5—H5	0.9500	C19—H19C	0.9800
C6—C7	1.422 (3)
O1—Zn1—N1	82.18 (7)	C6—C7—H7	120.2
O1—Zn1—N2	95.64 (7)	C7—C8—C9	119.7 (2)
N1—Zn1—N2	143.92 (8)	C7—C8—H8	120.1
O1—Zn1—Cl1	112.11 (5)	C9—C8—H8	120.1
N1—Zn1—Cl1	108.81 (6)	N1—C9—C8	122.2 (2)
N2—Zn1—Cl1	105.34 (6)	N1—C9—H9	118.9
O1—Zn1—O2	150.43 (7)	C8—C9—H9	118.9
N1—Zn1—O2	90.44 (6)	N2—C10—C15	122.63 (19)
N2—Zn1—O2	73.80 (6)	N2—C10—C11	117.76 (19)
Cl1—Zn1—O2	97.40 (5)	C15—C10—C11	119.6 (2)
C2—O1—Zn1	111.33 (13)	O2—C11—C12	125.2 (2)
C11—O2—Zn1	109.79 (12)	O2—C11—C10	115.16 (19)
C11—O2—H2	109 (2)	C12—C11—C10	119.6 (2)
Zn1—O2—H2	136 (2)	C11—C12—C13	120.4 (2)
C19—O3—H3	109 (2)	C11—C12—H12	119.8
C9—N1—C1	118.9 (2)	C13—C12—H12	119.8
C9—N1—Zn1	129.73 (17)	C14—C13—C12	121.6 (2)
C1—N1—Zn1	110.92 (14)	C14—C13—H13	119.2
C18—N2—C10	118.31 (19)	C12—C13—H13	119.2
C18—N2—Zn1	122.72 (15)	C13—C14—C15	119.2 (2)
C10—N2—Zn1	117.44 (14)	C13—C14—H14	120.4
N1—C1—C6	122.56 (19)	C15—C14—H14	120.4
N1—C1—C2	116.5 (2)	C10—C15—C14	119.6 (2)
C6—C1—C2	121.0 (2)	C10—C15—C16	117.0 (2)
O1—C2—C3	124.4 (2)	C14—C15—C16	123.4 (2)
O1—C2—C1	118.4 (2)	C17—C16—C15	119.6 (2)
C3—C2—C1	117.3 (2)	C17—C16—H16	120.2
C2—C3—C4	121.4 (2)	C15—C16—H16	120.2
C2—C3—H3A	119.3	C16—C17—C18	119.5 (2)
C4—C3—H3A	119.3	C16—C17—H17	120.2
C5—C4—C3	121.8 (2)	C18—C17—H17	120.2
C5—C4—H4	119.1	N2—C18—C17	122.8 (2)
C3—C4—H4	119.1	N2—C18—H18	118.6
C4—C5—C6	119.0 (2)	C17—C18—H18	118.6
C4—C5—H5	120.5	O3—C19—H19A	109.5
C6—C5—H5	120.5	O3—C19—H19B	109.5
C1—C6—C5	119.5 (2)	H19A—C19—H19B	109.5
C1—C6—C7	116.9 (2)	O3—C19—H19C	109.5
C5—C6—C7	123.6 (2)	H19A—C19—H19C	109.5
C8—C7—C6	119.7 (2)	H19B—C19—H19C	109.5
C8—C7—H7	120.2
N1—Zn1—O1—C2	−7.37 (15)	N1—C1—C6—C5	−178.8 (2)
N2—Zn1—O1—C2	−151.09 (15)	C2—C1—C6—C5	−0.1 (3)
Cl1—Zn1—O1—C2	99.82 (15)	N1—C1—C6—C7	0.9 (3)
O2—Zn1—O1—C2	−84.30 (18)	C2—C1—C6—C7	179.6 (2)
O1—Zn1—O2—C11	−92.97 (18)	C4—C5—C6—C1	−1.3 (3)
N1—Zn1—O2—C11	−167.77 (16)	C4—C5—C6—C7	179.1 (2)
N2—Zn1—O2—C11	−20.70 (15)	C1—C6—C7—C8	−0.8 (3)
Cl1—Zn1—O2—C11	83.19 (15)	C5—C6—C7—C8	178.9 (2)
O1—Zn1—N1—C9	179.1 (2)	C6—C7—C8—C9	0.1 (3)
N2—Zn1—N1—C9	−92.0 (2)	C1—N1—C9—C8	−0.5 (3)
Cl1—Zn1—N1—C9	68.3 (2)	Zn1—N1—C9—C8	−171.85 (17)
O2—Zn1—N1—C9	−29.6 (2)	C7—C8—C9—N1	0.6 (4)
O1—Zn1—N1—C1	7.27 (15)	C18—N2—C10—C15	−3.6 (3)
N2—Zn1—N1—C1	96.13 (18)	Zn1—N2—C10—C15	162.71 (18)
Cl1—Zn1—N1—C1	−103.50 (15)	C18—N2—C10—C11	175.6 (2)
O2—Zn1—N1—C1	158.53 (15)	Zn1—N2—C10—C11	−18.1 (3)
O1—Zn1—N2—C18	−22.1 (2)	Zn1—O2—C11—C12	−163.1 (2)
N1—Zn1—N2—C18	−106.6 (2)	Zn1—O2—C11—C10	18.3 (2)
Cl1—Zn1—N2—C18	92.65 (19)	N2—C10—C11—O2	−2.4 (3)
O2—Zn1—N2—C18	−173.9 (2)	C15—C10—C11—O2	176.8 (2)
O1—Zn1—N2—C10	172.22 (17)	N2—C10—C11—C12	178.9 (2)
N1—Zn1—N2—C10	87.8 (2)	C15—C10—C11—C12	−1.9 (4)
Cl1—Zn1—N2—C10	−73.00 (17)	O2—C11—C12—C13	−177.4 (2)
O2—Zn1—N2—C10	20.40 (16)	C10—C11—C12—C13	1.2 (4)
C9—N1—C1—C6	−0.3 (3)	C11—C12—C13—C14	−0.5 (4)
Zn1—N1—C1—C6	172.59 (18)	C12—C13—C14—C15	0.5 (4)
C9—N1—C1—C2	−179.0 (2)	N2—C10—C15—C14	−178.9 (2)
Zn1—N1—C1—C2	−6.1 (2)	C11—C10—C15—C14	2.0 (3)
Zn1—O1—C2—C3	−173.89 (19)	N2—C10—C15—C16	2.6 (3)
Zn1—O1—C2—C1	6.3 (3)	C11—C10—C15—C16	−176.6 (2)
N1—C1—C2—O1	−0.1 (3)	C13—C14—C15—C10	−1.3 (4)
C6—C1—C2—O1	−178.8 (2)	C13—C14—C15—C16	177.2 (2)
N1—C1—C2—C3	−179.9 (2)	C10—C15—C16—C17	0.9 (3)
C6—C1—C2—C3	1.3 (3)	C14—C15—C16—C17	−177.5 (2)
O1—C2—C3—C4	179.0 (2)	C15—C16—C17—C18	−3.2 (4)
C1—C2—C3—C4	−1.2 (3)	C10—N2—C18—C17	1.1 (4)
C2—C3—C4—C5	−0.2 (4)	Zn1—N2—C18—C17	−164.42 (19)
C3—C4—C5—C6	1.4 (4)	C16—C17—C18—N2	2.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.84 (1)	1.71 (1)	2.547 (2)	170 (3)
O3—H3···O1i	0.84 (1)	1.76 (1)	2.592 (2)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.84 (1)	1.71 (1)	2.547 (2)	170 (3)
O3—H3⋯O1i	0.84 (1)	1.76 (1)	2.592 (2)	176 (3)

Symmetry code: (i) .