Chlorido(8-hy­droxy­quinoline-κ2N,O)(quinolin-8-olato-κ2N,O)zinc methanol monosolvate

Najafi, E.; Amini, M.M.; Ng, S.W.

doi:10.1107/S160053681103337X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1283

doi:10.1107/S160053681103337X

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Chlorido(8-hydroxyquinoline-κ²N,O)(quinolin-8-olato-κ²N,O)zinc methanol monosolvate

Ezzatollah Najafi,^a Mostafa M. Amini ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 8 August 2011; accepted 16 August 2011; online 27 August 2011)

In the title compound, [Zn(C₉H₆NO)Cl(C₉H₇NO)]·CH₃OH, 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 intermolecular 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-κ²N,O)zincate(II) acetonitrile disolvate, see: Najafi et al. (2011 ).

Experimental

Crystal data

[Zn(C₉H₆NO)Cl(C₉H₇NO)]·CH₄O
M_r = 422.17
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.082
S = 1.05
3806 reflections
244 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.42 e Å⁻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) x, y+1, z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681103337X/lh5311sup1.cif

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

checkCIF report

Comment top

We have previously determined the structure of 8-Hydroxy-2-methylquinolinium dichlorido(2-methylquinolin-8-olato-κ²N,O)zincate(II) acetonitrile disolvate (Najafi et al., 2011). In the present study, the corresponding reaction of zinc chloride and the parent 8-hydroxyquinoline homolog in methanol yielded a neutral mono-solvated compound. The Zn^II atom in ZnCl(C₉H₆NO)(C₉H₇NO)]^.CH₃OH is N,O-chelated by a neutral as well as by a deprotonated 8-hydroxyquinoline ligand and it exists in a square-pyramidal geometry (Fig. 1). Adjacent molecules are linked by O–H···O hydrogen bonds through the solvent molecule to generate a linear chain running along the b-axis of the triclinic unit cell (Fig. 2).

Related literature top

For the crystal structure of 8-hydroxy-2-methylquinolinium dichlorido(2-methylquinolin-8-olato-κ²N,O)zincate(II) acetonitrile disolvate, see: Najafi et al. (2011).

Experimental top

Zinc chloride (0.13 g, 1 mmol) and 8-hydroxyquinoline (0.29 g, 2 mmol) were loaded into a convection tube and the tube was filled with methanol and kept at 333 K. Yellow crystals were collected from the side arm after several days.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of ZnCl(C₉H₆NO)(C₉H₇NO)]^.CH₃OH at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines.

Chlorido(8-hydroxyquinoline-κ²N,O)(quinolin-8-olato- κ²N,O)zincate methanol monosolvate top

Crystal data top

[Zn(C₉H₆NO)Cl(C₉H₇NO)]·CH₄O	Z = 2
M_r = 422.17	F(000) = 432
Triclinic, P1	D_x = 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

Data collection top

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 monochromator	R_int = 0.045
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.6°
ω scans	h = −8→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −10→10
T_min = 0.795, T_max = 0.795	l = −17→17
6878 measured reflections

Refinement top

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(F_o²) + (0.0336P)² + 0.2331P] where P = (F_o² + 2F_c²)/3
3806 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.47 e Å⁻³
2 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Zn(C₉H₆NO)Cl(C₉H₇NO)]·CH₄O	γ = 110.549 (5)°
M_r = 422.17	V = 859.58 (7) Å³
Triclinic, P1	Z = 2
a = 8.4110 (4) Å	Mo Kα radiation
b = 8.4692 (4) Å	µ = 1.61 mm⁻¹
c = 13.2667 (7) Å	T = 100 K
α = 99.905 (4)°	0.15 × 0.15 × 0.15 mm
β = 95.341 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3806 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3258 reflections with I > 2σ(I)
T_min = 0.795, T_max = 0.795	R_int = 0.045
6878 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	2 restraints
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.47 e Å⁻³
3806 reflections	Δρ_min = −0.42 e Å⁻³
244 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Zn(C₉H₆NO)Cl(C₉H₇NO)]·CH₄O
M_r	422.17
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.4110 (4), 8.4692 (4), 13.2667 (7)
α, β, γ (°)	99.905 (4), 95.341 (4), 110.549 (5)
V (Å³)	859.58 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.61
Crystal size (mm)	0.15 × 0.15 × 0.15

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.795, 0.795
No. of measured, independent and observed [I > 2σ(I)] reflections	6878, 3806, 3258
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.082, 1.05
No. of reflections	3806
No. of parameters	244
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.42

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z.

Acknowledgements

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Najafi, E., Amini, M. M. & Ng, S. W. (2011). Acta Cryst. E67, m1280. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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