8-Hy­droxy-2-methyl­quinolinium diiodido(2-methyl­quinolin-8-olato-κ2N,O)zincate

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

doi:10.1107/S1600536811032351

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1282

doi:10.1107/S1600536811032351

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8-Hydroxy-2-methylquinolinium diiodido(2-methylquinolin-8-olato-κ²N,O)zincate

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 4 August 2011; accepted 9 August 2011; online 27 August 2011)

The reaction of 2-methyl-8-hydroxyquinoline and zinc iodide in acetonitrile affords the title salt, (C₁₀H₁₀NO)[Zn(C₁₀H₈NO)I₂], in which the Zn^II ion is coordinated by a N,O-chelating 2-methylquinolin-8-olate ligand and two iodide ligands in a distorted tetrahedral 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_r = 637.53
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.087
S = 1.04
3765 reflections
247 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.99 e Å⁻³
Δρ_min = −1.53 e Å⁻³
Absolute structure: Flack (1983 ) 1389 Friedel pairs
Flack parameter: 0.01 (2)

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

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/S1600536811032351/lh5307sup1.cif

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

checkCIF report

Comment top

We have synthesized methanol-solvated 8-hydroxy-2-methylquinolinium dihalo(2-methylquinolin-8-olato)zincates(II) by the direct reaction of the zinc halide and 8-hydroxy-2-methylquinolin in methanol. The salts have the Zn^II atom in a tetrahedral geometry, and the ion-pairs are linked to the solvent molecules by hydrogen bonds (Najafi et al., 2010a; Najafi et al., 2010b; Sattarzadeh et al., 2009). These studies have been extended to the use of acetonitrile as a solvent. In a previous study, the reaction of zinc chloride/bromide and the quinoline in acetonitrile yielded the disolvated/monosolvated salts (Najafi et al., 2011a, 2011b). In the present study, using zinc iodide gave a solvent-free (Fig. 1) crystal structure. In (C₁₀H₁₀NO)[ZnI₂(C₁₀H₈NO)], the metal in the anion is N,O-chelated by the deprotonated ligand and it exists in a distorted tetrahedral geometry. The cation is linked to the anion by an O–H···O hydrogen bond (Table 1).

Related literature top

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 top

Zinc iodide (0.32 g, 0.75 mmol) and 2-methyl-8-hydroxyquinoline (0.24 g, 1.5 mmol) were loaded into a convection tube and the tube was filled with acetonitrile 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 (C₁₀H₁₀NO)[ZnI₂(C₁₀H₈NO)] at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

8-Hydroxy-2-methylquinolinium diiodido(2-methylquinolin-8-olato-κ²N,O)zincate top

Crystal data top

(C₁₀H₁₀NO)[Zn(C₁₀H₈NO)I₂]	F(000) = 608
M_r = 637.53	D_x = 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

Data collection top

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 monochromator	R_int = 0.025
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.6°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −17→18
T_min = 0.282, T_max = 0.485	l = −11→7
4995 measured reflections

Refinement top

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(F_o²) + (0.0676P)² + 0.3294P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3765 reflections	Δρ_max = 0.99 e Å⁻³
247 parameters	Δρ_min = −1.53 e Å⁻³
1 restraint	Absolute structure: Flack (1983) 1389 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (2)

Crystal data top

(C₁₀H₁₀NO)[Zn(C₁₀H₈NO)I₂]	V = 1022.61 (4) Å³
M_r = 637.53	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.1794 (2) Å	µ = 4.24 mm⁻¹
b = 13.9441 (3) Å	T = 100 K
c = 9.1838 (2) Å	0.40 × 0.30 × 0.20 mm
β = 102.503 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3765 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3692 reflections with I > 2σ(I)
T_min = 0.282, T_max = 0.485	R_int = 0.025
4995 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.087	Δρ_max = 0.99 e Å⁻³
S = 1.04	Δρ_min = −1.53 e Å⁻³
3765 reflections	Absolute structure: Flack (1983) 1389 Friedel pairs
247 parameters	Absolute structure parameter: 0.01 (2)
1 restraint

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	(C₁₀H₁₀NO)[Zn(C₁₀H₈NO)I₂]
M_r	637.53
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	8.1794 (2), 13.9441 (3), 9.1838 (2)
β (°)	102.503 (3)
V (Å³)	1022.61 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.24
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.282, 0.485
No. of measured, independent and observed [I > 2σ(I)] reflections	4995, 3765, 3692
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.087, 1.04
No. of reflections	3765
No. of parameters	247
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.99, −1.53
Absolute structure	Flack (1983) 1389 Friedel pairs
Absolute structure parameter	0.01 (2)

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—H2o···O1	0.84	1.71	2.542 (6)	170

Acknowledgements

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

References

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