8-Hy­droxy-2-methyl­quinolinium dibromido(2-methyl­quinolin-8-olato-κ2N,O)zincate acetonitrile mono­solvate

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

doi:10.1107/S160053681103234X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1281

doi:10.1107/S160053681103234X

Open

access

8-Hydroxy-2-methylquinolinium dibromido(2-methylquinolin-8-olato-κ²N,O)zincate acetonitrile 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 4 August 2011; accepted 9 August 2011; online 27 August 2011)

The reaction of 2-methyl-8-hydroxyquinoline and zinc bromide in acetonitrile affords the title solvated salt, (C₁₀H₁₀NO)[ZnBr₂(C₁₀H₈NO)]·CH₃CN, in which the Zn^II ion is coordinated by a N,O-chelating 2-methylquinolin-8-olate ligand and two bromide ligands in a distorted tetrahedral geometry. The cation is linked to the anion by an O—H⋯O hydrogen bond and the quinolinium H atom forms an intermolecular N—H⋯N hydrogen bond with the acetonitrile solvent molecule.

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_r = 584.61
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.065
S = 1.01
4970 reflections
282 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.86 e Å⁻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)

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/S160053681103234X/lh5306sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681103234X/lh5306Isup2.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). In this study we used acetonitrile as a solvent. In a previous study, the reaction of zinc chloride and the quinoline in acetonitrile yielded the disolvated salt (Najafi et al., 2011). In the present study, zinc dibromide gave a mono-solvated salt (Fig. 1). In (C₁₀H₁₀NO)[ZnBr₂(C₁₀H₈NO)]^.CH₃CN, 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 and the quinolinium H atom forms a hydrogen bond with the solvent molecule (Table 1).

Related literature top

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 top

Zinc chloride (0.23 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. Displacement ellipsoid plot (Barbour, 2001) of (C₁₀H₁₀NO)[ZnBr₂(C₁₀H₈NO)]^.CH₃CN at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

8-Hydroxy-2-methylquinolinium dibromido(2-methylquinolin-8-olato-κ²N,O)zincate acetonitrile monosolvate top

Crystal data top

(C₁₀H₁₀NO)[ZnBr₂(C₁₀H₈NO)]·C₂H₃N	Z = 2
M_r = 584.61	F(000) = 580
Triclinic, P1	D_x = 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

Data collection top

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 monochromator	R_int = 0.033
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −9→12
T_min = 0.387, T_max = 0.540	l = −20→21
8710 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)] = 0.031	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(F_o²) + (0.0183P)²] where P = (F_o² + 2F_c²)/3
4970 reflections	(Δ/σ)_max = 0.001
282 parameters	Δρ_max = 0.54 e Å⁻³
2 restraints	Δρ_min = −0.86 e Å⁻³

Crystal data top

(C₁₀H₁₀NO)[ZnBr₂(C₁₀H₈NO)]·C₂H₃N	γ = 85.098 (4)°
M_r = 584.61	V = 1121.73 (9) Å³
Triclinic, P1	Z = 2
a = 7.1870 (3) Å	Mo Kα radiation
b = 9.7795 (5) Å	µ = 4.68 mm⁻¹
c = 16.2520 (7) Å	T = 100 K
α = 86.159 (4)°	0.25 × 0.20 × 0.15 mm
β = 80.775 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4970 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	4197 reflections with I > 2σ(I)
T_min = 0.387, T_max = 0.540	R_int = 0.033
8710 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	2 restraints
wR(F²) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.54 e Å⁻³
4970 reflections	Δρ_min = −0.86 e Å⁻³
282 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	(C₁₀H₁₀NO)[ZnBr₂(C₁₀H₈NO)]·C₂H₃N
M_r	584.61
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.1870 (3), 9.7795 (5), 16.2520 (7)
α, β, γ (°)	86.159 (4), 80.775 (4), 85.098 (4)
V (Å³)	1121.73 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.68
Crystal size (mm)	0.25 × 0.20 × 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	0.387, 0.540
No. of measured, independent and observed [I > 2σ(I)] reflections	8710, 4970, 4197
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.065, 1.01
No. of reflections	4970
No. of parameters	282
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)	0.54, −0.86

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···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)

Acknowledgements

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

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, 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. (2010a). Acta Cryst. E66, m1276. Google Scholar
Najafi, E., Amini, M. M. & Ng, S. W. (2010b). Acta Cryst. E66, m1277. Google Scholar
Najafi, E., Amini, M. M. & Ng, S. W. (2011). Acta Cryst. E67, m1280. Google Scholar
Sattarzadeh, E., Mohammadnezhad, G., Amini, M. M. & Ng, S. W. (2009). Acta Cryst. E65, m553. Web of Science CSD CrossRef IUCr Journals 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.