8-Hydr­oxy-2-methyl­quinolinium dichlorido(2-methyl­quinolin-8-olato-κ2N,O)zincate(II) methanol solvate

Sattarzadeh, E.; Mohammadnezhad, G.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536809014202

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m553

doi:10.1107/S1600536809014202

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8-Hydroxy-2-methylquinolinium dichlorido(2-methylquinolin-8-olato-κ²N,O)zincate(II) methanol solvate

Elham Sattarzadeh,^a Gholamhossein Mohammadnezhad,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 April 2009; accepted 16 April 2009; online 22 April 2009)

The reaction of zinc chloride and 2-methyl-8-hydroxyquinoline in methanol yielded the title monosolvated salt, (C₁₀H₁₀NO)[ZnCl₂(C₁₀H₈NO)]·CH₃OH, which has the Zn atom within a distorted Cl₂NO tetrahedral coordination geometry. Supramolecular chains feature in the crystal structure, comprising all components of the structure stabilized by a combination of O—H⋯O, N—H⋯O and O—H⋯Cl hydrogen bonding.

Related literature

Unlike 8-hydroxyquinoline, which yields a large number of metal derivatives, 2-methyl-8-hydroxyquinoline forms only a small number of metal chelates. Besides a related acetate salt (Sattarzadeh et al., 2009 ), there is only one crystal structure report of another zinc derivative; for aquabis(2-methylquinolin-8-ato)zinc, see: da Silva et al. (2007 ).

Experimental

Crystal data

(C₁₀H₁₀NO)[ZnCl₂(C₁₀H₈NO)]·CH₄O
M_r = 486.68
Monoclinic, P 2₁ /n
a = 10.0717 (2) Å
b = 13.7886 (3) Å
c = 15.4828 (3) Å
β = 105.48 (1)°
V = 2072.15 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.47 mm⁻¹
T = 100 K
0.32 × 0.12 × 0.08 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.651, T_max = 0.892
18982 measured reflections
4753 independent reflections
3600 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.108
S = 1.02
4753 reflections
277 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.08 e Å⁻³
Δρ_min = −1.00 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O1	0.84 (1)	1.70 (1)	2.534 (3)	177 (4)
O3—H3O⋯Cl1ⁱ	0.84 (1)	2.47 (3)	3.239 (4)	153 (5)
N2—H2N⋯O3	0.88 (1)	1.87 (2)	2.727 (4)	163 (3)
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014202/tk2423sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014202/tk2423Isup2.hkl

checkCIF report

Related literature top

Unlike 8-hydroxyquinoline, which yields a large number of metal derivatives, 2-methyl-8-hydroxyquinoline forms only a small number of metal chelates. There is only one crystal structure report of a zinc derivative; for aquabis(2-methylquinolin-8-ato)zinc, see: da Silva et al. (2007).

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; the tube was filled with dry methanol and kept at 333 K. Crystals were collected from the side arm after several days.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [C₁₀H₁₀NO][Zn(C₁₀H₈NO)Cl₂]^.CH₃OH; ellipsoids are drawn at the 70% probability level and H atoms of arbitrary radius.

8-Hydroxy-2-methylquinolinium dichlorido(2-methylquinolin-8-olato-κ²N,O)zincate(II) methanol solvate top

Crystal data top

(C₁₀H₁₀NO)[ZnCl₂(C₁₀H₈NO)]·CH₄O	F(000) = 1000
M_r = 486.68	D_x = 1.560 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4908 reflections
a = 10.0717 (2) Å	θ = 2.6–27.1°
b = 13.7886 (3) Å	µ = 1.47 mm⁻¹
c = 15.4828 (3) Å	T = 100 K
β = 105.48 (1)°	Block, yellow
V = 2072.15 (7) Å³	0.32 × 0.12 × 0.08 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	4753 independent reflections
Radiation source: fine-focus sealed tube	3600 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.651, T_max = 0.892	k = −17→17
18982 measured reflections	l = −20→20

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0493P)² + 2.8684P] where P = (F_o² + 2F_c²)/3
4753 reflections	(Δ/σ)_max = 0.001
277 parameters	Δρ_max = 1.08 e Å⁻³
3 restraints	Δρ_min = −1.00 e Å⁻³

Crystal data top

(C₁₀H₁₀NO)[ZnCl₂(C₁₀H₈NO)]·CH₄O	V = 2072.15 (7) Å³
M_r = 486.68	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.0717 (2) Å	µ = 1.47 mm⁻¹
b = 13.7886 (3) Å	T = 100 K
c = 15.4828 (3) Å	0.32 × 0.12 × 0.08 mm
β = 105.48 (1)°

Data collection top

Bruker SMART APEX diffractometer	4753 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3600 reflections with I > 2σ(I)
T_min = 0.651, T_max = 0.892	R_int = 0.036
18982 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	3 restraints
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 1.08 e Å⁻³
4753 reflections	Δρ_min = −1.00 e Å⁻³
277 parameters

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

	x	y	z	U_iso*/U_eq
Zn1	0.50382 (3)	0.63261 (3)	0.23689 (2)	0.02655 (11)
Cl1	0.48941 (8)	0.76378 (6)	0.31836 (5)	0.03149 (18)
Cl2	0.39683 (8)	0.50528 (6)	0.27699 (5)	0.03503 (19)
O1	0.6980 (2)	0.60686 (17)	0.23887 (13)	0.0318 (5)
O2	0.9135 (2)	0.63848 (15)	0.36428 (13)	0.0258 (4)
H2O	0.843 (3)	0.626 (3)	0.3225 (19)	0.054 (13)*
O3	1.1916 (3)	0.6985 (4)	0.3410 (2)	0.1114 (18)
H3O	1.2770 (14)	0.706 (5)	0.353 (4)	0.11 (2)*
N1	0.4760 (2)	0.63643 (17)	0.10133 (15)	0.0232 (5)
N2	1.1439 (2)	0.64419 (17)	0.49938 (16)	0.0239 (5)
H2N	1.143 (4)	0.657 (3)	0.4435 (10)	0.040 (10)*
C1	0.7143 (3)	0.6004 (2)	0.15652 (19)	0.0257 (6)
C2	0.8383 (3)	0.5781 (2)	0.1389 (2)	0.0345 (7)
H2	0.9178	0.5676	0.1872	0.041*
C3	0.8481 (3)	0.5708 (2)	0.0502 (2)	0.0363 (8)
H3	0.9347	0.5557	0.0401	0.044*
C4	0.7372 (4)	0.5847 (2)	−0.0217 (2)	0.0344 (7)
H4	0.7466	0.5793	−0.0810	0.041*
C5	0.6079 (3)	0.6075 (2)	−0.00683 (19)	0.0280 (6)
C6	0.5975 (3)	0.6156 (2)	0.08206 (18)	0.0238 (6)
C7	0.4857 (4)	0.6220 (2)	−0.0757 (2)	0.0324 (7)
H7	0.4873	0.6172	−0.1366	0.039*
C8	0.3656 (3)	0.6428 (2)	−0.05527 (19)	0.0303 (7)
H8	0.2839	0.6530	−0.1020	0.036*
C9	0.3619 (3)	0.6491 (2)	0.03512 (19)	0.0259 (6)
C10	0.2318 (3)	0.6695 (2)	0.0599 (2)	0.0322 (7)
H10A	0.2445	0.7264	0.0992	0.048*
H10B	0.2074	0.6134	0.0914	0.048*
H10C	0.1577	0.6823	0.0056	0.048*
C11	0.8990 (3)	0.61926 (19)	0.44627 (18)	0.0211 (5)
C12	0.7783 (3)	0.5956 (2)	0.46570 (19)	0.0254 (6)
H12	0.6953	0.5926	0.4189	0.031*
C13	0.7759 (3)	0.5758 (2)	0.5544 (2)	0.0267 (6)
H13	0.6909	0.5594	0.5664	0.032*
C14	0.8927 (3)	0.5795 (2)	0.62372 (19)	0.0279 (6)
H14	0.8887	0.5657	0.6831	0.033*
C15	1.0188 (3)	0.6040 (2)	0.60665 (18)	0.0241 (6)
C16	1.0214 (3)	0.62310 (19)	0.51737 (18)	0.0218 (6)
C17	1.1463 (3)	0.6076 (2)	0.6733 (2)	0.0300 (7)
H17	1.1488	0.5961	0.7342	0.036*
C18	1.2650 (3)	0.6276 (2)	0.6509 (2)	0.0309 (7)
H18	1.3496	0.6293	0.6964	0.037*
C19	1.2646 (3)	0.6457 (2)	0.5617 (2)	0.0284 (6)
C20	1.3919 (3)	0.6644 (3)	0.5335 (2)	0.0381 (8)
H20A	1.3932	0.6227	0.4825	0.057*
H20B	1.4726	0.6504	0.5834	0.057*
H20C	1.3940	0.7326	0.5158	0.057*
C21	1.1182 (4)	0.7302 (3)	0.2615 (2)	0.0478 (9)
H21C	1.1577	0.7911	0.2471	0.072*
H21B	1.0228	0.7413	0.2632	0.072*
H21A	1.1200	0.6817	0.2156	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02484 (18)	0.0370 (2)	0.01749 (17)	−0.00010 (14)	0.00511 (13)	0.00387 (14)
Cl1	0.0333 (4)	0.0367 (4)	0.0238 (3)	−0.0047 (3)	0.0066 (3)	−0.0003 (3)
Cl2	0.0401 (4)	0.0349 (4)	0.0342 (4)	−0.0009 (3)	0.0170 (3)	0.0076 (3)
O1	0.0251 (11)	0.0528 (14)	0.0170 (10)	−0.0012 (10)	0.0047 (8)	0.0001 (9)
O2	0.0260 (10)	0.0327 (11)	0.0173 (10)	−0.0003 (9)	0.0032 (8)	0.0002 (8)
O3	0.0368 (18)	0.240 (5)	0.063 (2)	0.040 (2)	0.0233 (16)	0.091 (3)
N1	0.0269 (12)	0.0231 (12)	0.0180 (11)	−0.0054 (10)	0.0029 (9)	0.0023 (9)
N2	0.0252 (12)	0.0233 (12)	0.0219 (12)	0.0037 (10)	0.0037 (10)	0.0026 (10)
C1	0.0268 (15)	0.0291 (15)	0.0212 (14)	−0.0070 (12)	0.0063 (11)	−0.0022 (11)
C2	0.0294 (16)	0.0411 (19)	0.0340 (17)	−0.0086 (14)	0.0100 (13)	−0.0070 (14)
C3	0.0348 (18)	0.0404 (19)	0.0404 (19)	−0.0108 (14)	0.0216 (15)	−0.0121 (15)
C4	0.048 (2)	0.0317 (17)	0.0290 (16)	−0.0104 (15)	0.0197 (15)	−0.0057 (13)
C5	0.0413 (17)	0.0217 (14)	0.0222 (14)	−0.0087 (12)	0.0108 (13)	0.0003 (11)
C6	0.0286 (15)	0.0237 (14)	0.0189 (13)	−0.0073 (11)	0.0062 (11)	−0.0001 (10)
C7	0.053 (2)	0.0247 (15)	0.0175 (14)	−0.0061 (14)	0.0055 (13)	−0.0002 (11)
C8	0.0424 (18)	0.0250 (15)	0.0162 (13)	−0.0023 (13)	−0.0050 (12)	0.0019 (11)
C9	0.0306 (15)	0.0206 (14)	0.0230 (14)	−0.0036 (11)	0.0009 (12)	0.0017 (11)
C10	0.0299 (16)	0.0333 (16)	0.0288 (16)	0.0019 (13)	−0.0001 (13)	0.0029 (13)
C11	0.0276 (14)	0.0176 (13)	0.0170 (12)	0.0024 (11)	0.0041 (11)	0.0006 (10)
C12	0.0271 (15)	0.0254 (14)	0.0227 (14)	0.0006 (11)	0.0048 (12)	−0.0022 (11)
C13	0.0295 (15)	0.0253 (15)	0.0281 (15)	0.0009 (12)	0.0123 (12)	0.0011 (12)
C14	0.0379 (17)	0.0252 (15)	0.0210 (14)	0.0042 (13)	0.0086 (12)	0.0017 (11)
C15	0.0306 (15)	0.0196 (13)	0.0209 (14)	0.0044 (11)	0.0049 (11)	−0.0026 (11)
C16	0.0266 (14)	0.0181 (13)	0.0199 (13)	0.0033 (11)	0.0047 (11)	−0.0005 (10)
C17	0.0380 (17)	0.0286 (16)	0.0198 (14)	0.0054 (13)	0.0016 (12)	−0.0013 (12)
C18	0.0282 (15)	0.0321 (16)	0.0260 (15)	0.0031 (13)	−0.0040 (12)	−0.0026 (12)
C19	0.0274 (15)	0.0230 (15)	0.0307 (16)	0.0033 (12)	0.0005 (12)	0.0000 (12)
C20	0.0264 (16)	0.0411 (19)	0.043 (2)	−0.0007 (14)	0.0029 (14)	0.0084 (15)
C21	0.048 (2)	0.057 (2)	0.040 (2)	−0.0010 (18)	0.0137 (17)	0.0023 (18)

Geometric parameters (Å, º) top

Zn1—N1	2.043 (2)	C8—H8	0.9500
Zn1—O1	1.980 (2)	C9—C10	1.488 (4)
Zn1—Cl1	2.2318 (8)	C10—H10A	0.9800
Zn1—Cl2	2.2331 (8)	C10—H10B	0.9800
O1—C1	1.331 (3)	C10—H10C	0.9800
O2—C11	1.342 (3)	C11—C12	1.368 (4)
O2—H2O	0.841 (10)	C11—C16	1.418 (4)
O3—C21	1.329 (5)	C12—C13	1.407 (4)
O3—H3O	0.836 (10)	C12—H12	0.9500
N1—C9	1.332 (4)	C13—C14	1.365 (4)
N1—C6	1.365 (4)	C13—H13	0.9500
N2—C19	1.335 (4)	C14—C15	1.406 (4)
N2—C16	1.367 (4)	C14—H14	0.9500
N2—H2N	0.881 (10)	C15—C16	1.414 (4)
C1—C2	1.382 (4)	C15—C17	1.417 (4)
C1—C6	1.426 (4)	C17—C18	1.359 (5)
C2—C3	1.406 (4)	C17—H17	0.9500
C2—H2	0.9500	C18—C19	1.402 (4)
C3—C4	1.364 (5)	C18—H18	0.9500
C3—H3	0.9500	C19—C20	1.484 (4)
C4—C5	1.417 (5)	C20—H20A	0.9800
C4—H4	0.9500	C20—H20B	0.9800
C5—C7	1.411 (4)	C20—H20C	0.9800
C5—C6	1.412 (4)	C21—H21C	0.9800
C7—C8	1.360 (5)	C21—H21B	0.9800
C7—H7	0.9500	C21—H21A	0.9800
C8—C9	1.413 (4)

O1—Zn1—N1	83.36 (9)	H10A—C10—H10B	109.5
O1—Zn1—Cl1	110.46 (7)	C9—C10—H10C	109.5
N1—Zn1—Cl1	123.24 (7)	H10A—C10—H10C	109.5
O1—Zn1—Cl2	113.75 (7)	H10B—C10—H10C	109.5
N1—Zn1—Cl2	111.22 (7)	O2—C11—C12	125.6 (3)
Cl1—Zn1—Cl2	111.78 (3)	O2—C11—C16	115.8 (2)
C1—O1—Zn1	111.79 (18)	C12—C11—C16	118.5 (3)
C11—O2—H2O	114 (3)	C11—C12—C13	120.6 (3)
C21—O3—H3O	117 (4)	C11—C12—H12	119.7
C9—N1—C6	119.9 (2)	C13—C12—H12	119.7
C9—N1—Zn1	130.4 (2)	C14—C13—C12	121.6 (3)
C6—N1—Zn1	109.52 (18)	C14—C13—H13	119.2
C19—N2—C16	123.6 (3)	C12—C13—H13	119.2
C19—N2—H2N	118 (2)	C13—C14—C15	119.6 (3)
C16—N2—H2N	118 (2)	C13—C14—H14	120.2
O1—C1—C2	123.6 (3)	C15—C14—H14	120.2
O1—C1—C6	118.6 (3)	C14—C15—C16	118.8 (3)
C2—C1—C6	117.8 (3)	C14—C15—C17	124.1 (3)
C1—C2—C3	120.7 (3)	C16—C15—C17	117.0 (3)
C1—C2—H2	119.6	N2—C16—C15	119.5 (3)
C3—C2—H2	119.6	N2—C16—C11	119.7 (2)
C4—C3—C2	122.2 (3)	C15—C16—C11	120.9 (3)
C4—C3—H3	118.9	C18—C17—C15	120.7 (3)
C2—C3—H3	118.9	C18—C17—H17	119.7
C3—C4—C5	119.0 (3)	C15—C17—H17	119.7
C3—C4—H4	120.5	C17—C18—C19	121.0 (3)
C5—C4—H4	120.5	C17—C18—H18	119.5
C7—C5—C6	116.7 (3)	C19—C18—H18	119.5
C7—C5—C4	124.2 (3)	N2—C19—C18	118.1 (3)
C6—C5—C4	119.1 (3)	N2—C19—C20	118.8 (3)
N1—C6—C5	122.2 (3)	C18—C19—C20	123.0 (3)
N1—C6—C1	116.6 (2)	C19—C20—H20A	109.5
C5—C6—C1	121.1 (3)	C19—C20—H20B	109.5
C8—C7—C5	120.3 (3)	H20A—C20—H20B	109.5
C8—C7—H7	119.8	C19—C20—H20C	109.5
C5—C7—H7	119.8	H20A—C20—H20C	109.5
C7—C8—C9	120.2 (3)	H20B—C20—H20C	109.5
C7—C8—H8	119.9	O3—C21—H21C	109.5
C9—C8—H8	119.9	O3—C21—H21B	109.5
N1—C9—C8	120.6 (3)	H21C—C21—H21B	109.5
N1—C9—C10	117.7 (3)	O3—C21—H21A	109.5
C8—C9—C10	121.7 (3)	H21C—C21—H21A	109.5
C9—C10—H10A	109.5	H21B—C21—H21A	109.5
C9—C10—H10B	109.5

N1—Zn1—O1—C1	−2.8 (2)	C5—C7—C8—C9	−0.5 (4)
Cl1—Zn1—O1—C1	−125.81 (18)	C6—N1—C9—C8	−1.0 (4)
Cl2—Zn1—O1—C1	107.55 (19)	Zn1—N1—C9—C8	−175.8 (2)
O1—Zn1—N1—C9	178.1 (3)	C6—N1—C9—C10	178.7 (3)
Cl1—Zn1—N1—C9	−71.7 (3)	Zn1—N1—C9—C10	3.8 (4)
Cl2—Zn1—N1—C9	65.2 (3)	C7—C8—C9—N1	1.0 (4)
O1—Zn1—N1—C6	2.88 (18)	C7—C8—C9—C10	−178.6 (3)
Cl1—Zn1—N1—C6	113.03 (17)	O2—C11—C12—C13	179.2 (3)
Cl2—Zn1—N1—C6	−110.05 (17)	C16—C11—C12—C13	0.1 (4)
Zn1—O1—C1—C2	−176.7 (3)	C11—C12—C13—C14	0.1 (4)
Zn1—O1—C1—C6	2.2 (3)	C12—C13—C14—C15	0.1 (4)
O1—C1—C2—C3	178.9 (3)	C13—C14—C15—C16	−0.7 (4)
C6—C1—C2—C3	0.1 (5)	C13—C14—C15—C17	−178.4 (3)
C1—C2—C3—C4	−0.3 (5)	C19—N2—C16—C15	1.7 (4)
C2—C3—C4—C5	0.1 (5)	C19—N2—C16—C11	−177.4 (3)
C3—C4—C5—C7	−179.0 (3)	C14—C15—C16—N2	−178.1 (3)
C3—C4—C5—C6	0.3 (4)	C17—C15—C16—N2	−0.2 (4)
C9—N1—C6—C5	0.5 (4)	C14—C15—C16—C11	0.9 (4)
Zn1—N1—C6—C5	176.3 (2)	C17—C15—C16—C11	178.9 (2)
C9—N1—C6—C1	−178.4 (3)	O2—C11—C16—N2	−0.8 (4)
Zn1—N1—C6—C1	−2.6 (3)	C12—C11—C16—N2	178.4 (2)
C7—C5—C6—N1	−0.1 (4)	O2—C11—C16—C15	−179.9 (2)
C4—C5—C6—N1	−179.4 (3)	C12—C11—C16—C15	−0.7 (4)
C7—C5—C6—C1	178.8 (3)	C14—C15—C17—C18	177.0 (3)
C4—C5—C6—C1	−0.6 (4)	C16—C15—C17—C18	−0.8 (4)
O1—C1—C6—N1	0.4 (4)	C15—C17—C18—C19	0.5 (5)
C2—C1—C6—N1	179.3 (3)	C16—N2—C19—C18	−2.0 (4)
O1—C1—C6—C5	−178.6 (3)	C16—N2—C19—C20	176.8 (3)
C2—C1—C6—C5	0.4 (4)	C17—C18—C19—N2	0.9 (4)
C6—C5—C7—C8	0.1 (4)	C17—C18—C19—C20	−177.8 (3)
C4—C5—C7—C8	179.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1	0.84 (1)	1.70 (1)	2.534 (3)	177 (4)
O3—H3O···Cl1ⁱ	0.84 (1)	2.47 (3)	3.239 (4)	153 (5)
N2—H2N···O3	0.88 (1)	1.87 (2)	2.727 (4)	163 (3)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	(C₁₀H₁₀NO)[ZnCl₂(C₁₀H₈NO)]·CH₄O
M_r	486.68
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.0717 (2), 13.7886 (3), 15.4828 (3)
β (°)	105.48 (1)
V (Å³)	2072.15 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.47
Crystal size (mm)	0.32 × 0.12 × 0.08

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.651, 0.892
No. of measured, independent and observed [I > 2σ(I)] reflections	18982, 4753, 3600
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.108, 1.02
No. of reflections	4753
No. of parameters	277
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.08, −1.00

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1	0.84 (1)	1.70 (1)	2.534 (3)	177 (4)
O3—H3O···Cl1ⁱ	0.84 (1)	2.47 (3)	3.239 (4)	153 (5)
N2—H2N···O3	0.88 (1)	1.87 (2)	2.727 (4)	163 (3)

Symmetry code: (i) x+1, y, z.

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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Silva, L. E. da, Joussef, A. C., Rebelo, R. A., Foro, S. & Schmidt, B. (2007). Acta Cryst. E63, m129–m131. Web of Science CSD CrossRef IUCr Journals Google Scholar
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