8-Hy­droxy-2-methyl­quinolinium dichlorido(2-methyl­quinolin-8-olato-κ2N,O)zincate acetonitrile disolvate

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

doi:10.1107/S1600536811032338

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1280

doi:10.1107/S1600536811032338

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8-Hydroxy-2-methylquinolinium dichlorido(2-methylquinolin-8-olato-κ²N,O)zincate acetonitrile disolvate

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 chloride in acetonitrile affords the title solvated salt, (C₁₀H₁₀NO)[Zn(C₁₀H₈NO)Cl₂]·2CH₃CN, in which the Zn^II atom is coordinated by an N,O-chelating 2-methylquinolin-8-olate ligand and two chloride ligands in a distorted tetrahedral geometry. The cation is linked to the heterocyclic anion by an O—H⋯O hydrogen bond and the quinolinium H atom forms a intermolecular N—H⋯N hydrogen bond with one of the acetonitrile solvent molecules.

Related literature

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

Experimental

Crystal data

(C₁₀H₁₀NO)[Zn(C₁₀H₈NO)Cl₂]·2C₂H₃N
M_r = 536.74
Monoclinic, P 2₁ /n
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 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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.070
S = 1.04
5349 reflections
310 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.38 e Å⁻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)

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/S1600536811032338/lh5305sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032338/lh5305Isup2.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 a zinc halide and 8-hydroxy-2-methylquinoline in methanol. In these salts, the Zn^II ion is 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 the present study, the corresponding reaction of zinc chloride and the quinoline in acetonitrile yielded an analogous solvated salt (Fig. 1). In (C₁₀H₁₀NO)[ZnCl₂(C₁₀H₈NO)]^.2CH₃CN, 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 one of the solvent molecules (Table 1).

Related literature top

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

Experimental top

Zinc chloride (0.10 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)[ZnCl₂(C₁₀H₈NO)]^.2CH₃CN at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

8-Hydroxy-2-methylquinolinium dichlorido(2-methylquinolin-8-olato-κ²N,O)zincate acetonitrile disolvate top

Crystal data top

(C₁₀H₁₀NO)[Zn(C₁₀H₈NO)Cl₂]·2C₂H₃N	F(000) = 1104
M_r = 536.74	D_x = 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

Data collection top

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 monochromator	R_int = 0.026
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.6°
ω scans	h = −10→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −19→30
T_min = 0.664, T_max = 0.741	l = −13→12
11981 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)] = 0.029	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(F_o²) + (0.0274P)² + 0.9529P] where P = (F_o² + 2F_c²)/3
5349 reflections	(Δ/σ)_max = 0.001
310 parameters	Δρ_max = 0.38 e Å⁻³
2 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

(C₁₀H₁₀NO)[Zn(C₁₀H₈NO)Cl₂]·2C₂H₃N	V = 2402.43 (8) Å³
M_r = 536.74	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.9913 (2) Å	µ = 1.27 mm⁻¹
b = 23.1642 (5) Å	T = 100 K
c = 10.4317 (2) Å	0.35 × 0.30 × 0.25 mm
β = 95.687 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5349 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	4576 reflections with I > 2σ(I)
T_min = 0.664, T_max = 0.741	R_int = 0.026
11981 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	2 restraints
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.38 e Å⁻³
5349 reflections	Δρ_min = −0.38 e Å⁻³
310 parameters

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	(C₁₀H₁₀NO)[Zn(C₁₀H₈NO)Cl₂]·2C₂H₃N
M_r	536.74
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.9913 (2), 23.1642 (5), 10.4317 (2)
β (°)	95.687 (2)
V (Å³)	2402.43 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.27
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.664, 0.741
No. of measured, independent and observed [I > 2σ(I)] reflections	11981, 5349, 4576
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.070, 1.04
No. of reflections	5349
No. of parameters	310
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)	0.38, −0.38

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
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)

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
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Sattarzadeh, E., Mohammadnezhad, G., Amini, M. M. & Ng, S. W. (2009). Acta Cryst. E65, m553. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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