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

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

doi:10.1107/S1600536810036706

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1276

doi:10.1107/S1600536810036706

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

Ezzatollah Najafi,^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 12 September 2010; accepted 14 September 2010; online 18 September 2010)

The anion of the title salt, (C₁₀H₁₀NO)[ZnBr₂(C₁₀H₈NO)]·CH₃OH, has its metal atom N,O-chelated by the deprotonated 2-methyl-8-hydroxyquinoline ligand. The hydroxy unit of the cation is a hydrogen-bond donor to the alkoxide O atom of the tetrahedrally coordinated anion, whereas the ammonium cation is a hydrogen-bond donor to the methanolic O atom. In the crystal, adjacent ion pairs and solvent molecules are linked by a methanol–halogen O—H⋯Br hydrogen bond, generating a chain running along the a axis.

Related literature

For the isostructural chloro analog, see: Sattarzadeh et al. (2009 ).

Experimental

Crystal data

(C₁₀H₁₀NO)[ZnBr₂(C₁₀H₈NO)]·CH₄O
M_r = 575.60
Monoclinic, P 2₁ /n
a = 9.9704 (8) Å
b = 13.9954 (11) Å
c = 15.8815 (12) Å
β = 105.815 (1)°
V = 2132.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 4.93 mm⁻¹
T = 100 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.278, T_max = 0.372
19908 measured reflections
4889 independent reflections
4044 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.057
S = 1.03
4889 reflections
267 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.37 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	1.71	2.546 (2)	172
O3—H3⋯Br1ⁱ	0.84	2.48	3.2941 (17)	163
N2—H2n⋯O3	0.86	1.91	2.739 (3)	162
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036706/bt5354sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810036706/bt5354Isup2.hkl

checkCIF report

Comment top

An earlier study reported C₁₀H₁₀NO^+.ZnCI₂(C₁₀H₈NO)^.CH₃OH, which feature cations, tetrahedral anions and solvent molecules linked by N···O, O···O and O···Cl hydrogen bonds into a linear chain (Sattarzadeh et al., 2009). The present bromide analog (Scheme I, Fig. 1) is isostructural, the two compounds displaying matching cell dimensions. The hydroxy unit of the cation is hydrogen-bond donor to the alkoxide O atom of the tetrahedrally coordinated anion whereas the ammonium unit is hydrogen-bond donor to the methanolic O atom. Adjacent ion-pairs and solvent molecules are linked by a O–H_methanol···Br hydrogen bond to generate a linear chain running along the a-axis of the monoclinic unit cell.

Related literature top

For the isostructural chloro analog, see: Sattarzadeh et al. (2009).

Experimental top

Zinc bromide (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, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound 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(II) methanol monosolvate top

Crystal data top

(C₁₀H₁₀NO)[ZnBr₂(C₁₀H₈NO)]·CH₄O	F(000) = 1144
M_r = 575.60	D_x = 1.793 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6099 reflections
a = 9.9704 (8) Å	θ = 2.6–28.2°
b = 13.9954 (11) Å	µ = 4.93 mm⁻¹
c = 15.8815 (12) Å	T = 100 K
β = 105.815 (1)°	Prism, yellow
V = 2132.2 (3) Å³	0.35 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	4889 independent reflections
Radiation source: fine-focus sealed tube	4044 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.278, T_max = 0.372	k = −18→18
19908 measured reflections	l = −19→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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.057	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0224P)² + 0.8543P] where P = (F_o² + 2F_c²)/3
4889 reflections	(Δ/σ)_max = 0.001
267 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

(C₁₀H₁₀NO)[ZnBr₂(C₁₀H₈NO)]·CH₄O	V = 2132.2 (3) Å³
M_r = 575.60	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.9704 (8) Å	µ = 4.93 mm⁻¹
b = 13.9954 (11) Å	T = 100 K
c = 15.8815 (12) Å	0.35 × 0.30 × 0.25 mm
β = 105.815 (1)°

Data collection top

Bruker SMART APEX diffractometer	4889 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4044 reflections with I > 2σ(I)
T_min = 0.278, T_max = 0.372	R_int = 0.040
19908 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.057	H-atom parameters constrained
S = 1.03	Δρ_max = 0.49 e Å⁻³
4889 reflections	Δρ_min = −0.37 e Å⁻³
267 parameters

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

	x	y	z	U_iso*/U_eq
Br1	1.00294 (2)	0.228905 (17)	0.184698 (15)	0.01708 (6)
Br2	1.12097 (3)	0.497149 (17)	0.227454 (16)	0.02018 (7)
Zn1	0.99449 (3)	0.369708 (19)	0.266658 (17)	0.01403 (7)
O1	0.79813 (16)	0.40171 (12)	0.25997 (10)	0.0166 (4)
O2	0.58392 (16)	0.36051 (12)	0.13590 (10)	0.0155 (3)
H2	0.6590	0.3718	0.1741	0.023*
O3	0.30839 (18)	0.27619 (14)	0.15184 (11)	0.0255 (4)
H3	0.2240	0.2660	0.1482	0.038*
N1	1.01652 (19)	0.36488 (13)	0.39831 (12)	0.0120 (4)
N2	0.35285 (19)	0.35026 (13)	0.00209 (12)	0.0129 (4)
H2N	0.3540	0.3348	0.0547	0.015*
C1	0.8930 (2)	0.38963 (15)	0.41453 (15)	0.0124 (5)
C2	0.7784 (2)	0.40932 (16)	0.33955 (15)	0.0141 (5)
C3	0.6537 (2)	0.43641 (17)	0.35416 (16)	0.0168 (5)
H3a	0.5762	0.4505	0.3058	0.020*
C4	0.6399 (3)	0.44345 (17)	0.43988 (16)	0.0181 (5)
H4	0.5525	0.4619	0.4480	0.022*
C5	0.7483 (3)	0.42455 (17)	0.51175 (16)	0.0185 (5)
H5	0.7362	0.4295	0.5689	0.022*
C6	0.8786 (2)	0.39750 (16)	0.50003 (15)	0.0143 (5)
C7	0.9995 (3)	0.37848 (16)	0.56932 (15)	0.0169 (5)
H7	0.9952	0.3826	0.6283	0.020*
C8	1.1213 (3)	0.35443 (16)	0.55191 (15)	0.0157 (5)
H8	1.2016	0.3415	0.5987	0.019*
C9	1.1288 (2)	0.34858 (15)	0.46464 (15)	0.0140 (5)
C10	1.2609 (2)	0.32358 (17)	0.44237 (16)	0.0177 (5)
H10A	1.2913	0.3781	0.4135	0.027*
H10B	1.2447	0.2683	0.4030	0.027*
H10C	1.3332	0.3079	0.4961	0.027*
C11	0.4758 (2)	0.37589 (15)	−0.01425 (15)	0.0124 (5)
C12	0.5986 (2)	0.38162 (15)	0.05651 (15)	0.0127 (5)
C13	0.7208 (2)	0.40884 (16)	0.03862 (15)	0.0144 (5)
H13	0.8044	0.4129	0.0847	0.017*
C14	0.7223 (2)	0.43073 (16)	−0.04781 (16)	0.0157 (5)
H14	0.8076	0.4494	−0.0588	0.019*
C15	0.6052 (2)	0.42585 (16)	−0.11591 (15)	0.0157 (5)
H15	0.6090	0.4413	−0.1735	0.019*
C16	0.4782 (2)	0.39768 (15)	−0.10042 (15)	0.0133 (5)
C17	0.3494 (2)	0.39320 (16)	−0.16628 (16)	0.0164 (5)
H17	0.3470	0.4067	−0.2253	0.020*
C18	0.2294 (3)	0.36989 (16)	−0.14609 (16)	0.0178 (5)
H18	0.1438	0.3684	−0.1908	0.021*
C19	0.2312 (2)	0.34802 (16)	−0.05948 (15)	0.0152 (5)
C20	0.1026 (2)	0.32331 (18)	−0.03312 (17)	0.0212 (5)
H20A	0.1008	0.3598	0.0192	0.032*
H20B	0.1025	0.2548	−0.0204	0.032*
H20C	0.0202	0.3392	−0.0809	0.032*
C21	0.3867 (3)	0.27543 (19)	0.24135 (16)	0.0218 (5)
H21A	0.4864	0.2742	0.2452	0.033*
H21B	0.3623	0.2186	0.2701	0.033*
H21C	0.3652	0.3329	0.2704	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01686 (12)	0.02067 (12)	0.01393 (12)	−0.00406 (9)	0.00458 (9)	−0.00180 (9)
Br2	0.02141 (13)	0.02021 (12)	0.02170 (14)	−0.00056 (10)	0.01060 (11)	0.00474 (10)
Zn1	0.01209 (14)	0.02082 (14)	0.00922 (14)	−0.00032 (11)	0.00298 (10)	0.00126 (11)
O1	0.0102 (8)	0.0304 (9)	0.0080 (8)	0.0014 (7)	0.0003 (6)	0.0007 (7)
O2	0.0124 (8)	0.0244 (9)	0.0078 (8)	−0.0009 (7)	−0.0005 (6)	0.0012 (7)
O3	0.0159 (9)	0.0454 (12)	0.0159 (9)	−0.0032 (9)	0.0056 (7)	0.0036 (8)
N1	0.0126 (9)	0.0126 (9)	0.0103 (9)	−0.0021 (8)	0.0024 (8)	0.0006 (7)
N2	0.0143 (10)	0.0131 (9)	0.0103 (10)	0.0007 (8)	0.0019 (8)	0.0002 (7)
C1	0.0154 (12)	0.0108 (10)	0.0119 (11)	−0.0042 (9)	0.0051 (9)	−0.0005 (8)
C2	0.0157 (12)	0.0144 (11)	0.0119 (12)	−0.0035 (9)	0.0032 (9)	0.0000 (9)
C3	0.0130 (11)	0.0203 (12)	0.0154 (12)	−0.0033 (9)	0.0011 (10)	0.0006 (9)
C4	0.0150 (12)	0.0197 (12)	0.0217 (13)	−0.0031 (10)	0.0084 (10)	−0.0042 (10)
C5	0.0270 (14)	0.0165 (12)	0.0152 (12)	−0.0053 (10)	0.0113 (11)	−0.0031 (10)
C6	0.0189 (12)	0.0124 (11)	0.0116 (11)	−0.0042 (9)	0.0043 (10)	0.0006 (9)
C7	0.0262 (13)	0.0152 (12)	0.0090 (12)	−0.0049 (10)	0.0045 (10)	−0.0006 (9)
C8	0.0197 (12)	0.0131 (11)	0.0120 (12)	−0.0016 (9)	0.0003 (10)	0.0007 (9)
C9	0.0177 (12)	0.0097 (11)	0.0144 (12)	−0.0032 (9)	0.0039 (10)	0.0010 (9)
C10	0.0158 (12)	0.0202 (12)	0.0153 (13)	0.0008 (10)	0.0013 (10)	0.0005 (10)
C11	0.0160 (12)	0.0095 (10)	0.0118 (11)	0.0033 (9)	0.0041 (9)	−0.0007 (8)
C12	0.0153 (11)	0.0120 (11)	0.0100 (11)	0.0022 (9)	0.0018 (9)	−0.0016 (8)
C13	0.0114 (11)	0.0165 (11)	0.0140 (12)	0.0022 (9)	0.0012 (9)	−0.0018 (9)
C14	0.0142 (12)	0.0155 (11)	0.0199 (13)	0.0023 (9)	0.0090 (10)	−0.0004 (9)
C15	0.0212 (13)	0.0161 (11)	0.0112 (12)	0.0023 (10)	0.0065 (10)	−0.0001 (9)
C16	0.0168 (12)	0.0108 (10)	0.0115 (11)	0.0049 (9)	0.0021 (9)	−0.0008 (9)
C17	0.0217 (13)	0.0139 (11)	0.0134 (12)	0.0052 (9)	0.0042 (10)	−0.0012 (9)
C18	0.0175 (12)	0.0186 (12)	0.0144 (12)	0.0021 (10)	−0.0009 (10)	−0.0022 (9)
C19	0.0152 (12)	0.0114 (11)	0.0175 (13)	0.0007 (9)	0.0017 (10)	−0.0005 (9)
C20	0.0145 (12)	0.0254 (13)	0.0220 (14)	−0.0006 (10)	0.0023 (11)	0.0035 (11)
C21	0.0207 (13)	0.0275 (14)	0.0160 (13)	−0.0011 (11)	0.0032 (10)	0.0022 (10)

Geometric parameters (Å, º) top

Br1—Zn1	2.3758 (4)	C8—H8	0.9500
Br2—Zn1	2.3637 (4)	C9—C10	1.496 (3)
Zn1—O1	1.9828 (16)	C10—H10A	0.9800
Zn1—N1	2.0431 (19)	C10—H10B	0.9800
O1—C2	1.335 (3)	C10—H10C	0.9800
O2—C12	1.341 (3)	C11—C16	1.409 (3)
O2—H2	0.8400	C11—C12	1.421 (3)
O3—C21	1.423 (3)	C12—C13	1.378 (3)
O3—H3	0.8400	C13—C14	1.411 (3)
N1—C9	1.331 (3)	C13—H13	0.9500
N1—C1	1.370 (3)	C14—C15	1.359 (3)
N2—C19	1.335 (3)	C14—H14	0.9500
N2—C11	1.368 (3)	C15—C16	1.411 (3)
N2—H2N	0.8600	C15—H15	0.9500
C1—C6	1.408 (3)	C16—C17	1.419 (3)
C1—C2	1.434 (3)	C17—C18	1.360 (3)
C2—C3	1.379 (3)	C17—H17	0.9500
C3—C4	1.409 (3)	C18—C19	1.404 (3)
C3—H3a	0.9500	C18—H18	0.9500
C4—C5	1.367 (3)	C19—C20	1.494 (3)
C4—H4	0.9500	C20—H20A	0.9800
C5—C6	1.414 (3)	C20—H20B	0.9800
C5—H5	0.9500	C20—H20C	0.9800
C6—C7	1.418 (3)	C21—H21A	0.9800
C7—C8	1.359 (3)	C21—H21B	0.9800
C7—H7	0.9500	C21—H21C	0.9800
C8—C9	1.411 (3)

O1—Zn1—N1	83.77 (7)	H10A—C10—H10B	109.5
O1—Zn1—Br2	113.91 (5)	C9—C10—H10C	109.5
N1—Zn1—Br2	112.22 (5)	H10A—C10—H10C	109.5
O1—Zn1—Br1	109.87 (5)	H10B—C10—H10C	109.5
N1—Zn1—Br1	121.55 (5)	N2—C11—C16	119.6 (2)
Br2—Zn1—Br1	112.362 (14)	N2—C11—C12	119.2 (2)
C2—O1—Zn1	111.41 (13)	C16—C11—C12	121.1 (2)
C12—O2—H2	109.5	O2—C12—C13	125.7 (2)
C21—O3—H3	109.5	O2—C12—C11	116.1 (2)
C9—N1—C1	119.98 (19)	C13—C12—C11	118.2 (2)
C9—N1—Zn1	130.41 (16)	C12—C13—C14	120.4 (2)
C1—N1—Zn1	109.43 (14)	C12—C13—H13	119.8
C19—N2—C11	123.3 (2)	C14—C13—H13	119.8
C19—N2—H2N	118.3	C15—C14—C13	121.9 (2)
C11—N2—H2N	118.3	C15—C14—H14	119.0
N1—C1—C6	122.3 (2)	C13—C14—H14	119.0
N1—C1—C2	116.5 (2)	C14—C15—C16	119.5 (2)
C6—C1—C2	121.2 (2)	C14—C15—H15	120.3
O1—C2—C3	123.6 (2)	C16—C15—H15	120.3
O1—C2—C1	118.8 (2)	C11—C16—C15	118.9 (2)
C3—C2—C1	117.6 (2)	C11—C16—C17	117.1 (2)
C2—C3—C4	120.8 (2)	C15—C16—C17	124.0 (2)
C2—C3—H3a	119.6	C18—C17—C16	120.9 (2)
C4—C3—H3a	119.6	C18—C17—H17	119.5
C5—C4—C3	122.0 (2)	C16—C17—H17	119.5
C5—C4—H4	119.0	C17—C18—C19	120.4 (2)
C3—C4—H4	119.0	C17—C18—H18	119.8
C4—C5—C6	119.2 (2)	C19—C18—H18	119.8
C4—C5—H5	120.4	N2—C19—C18	118.6 (2)
C6—C5—H5	120.4	N2—C19—C20	118.6 (2)
C1—C6—C5	119.1 (2)	C18—C19—C20	122.8 (2)
C1—C6—C7	116.5 (2)	C19—C20—H20A	109.5
C5—C6—C7	124.4 (2)	C19—C20—H20B	109.5
C8—C7—C6	120.4 (2)	H20A—C20—H20B	109.5
C8—C7—H7	119.8	C19—C20—H20C	109.5
C6—C7—H7	119.8	H20A—C20—H20C	109.5
C7—C8—C9	120.3 (2)	H20B—C20—H20C	109.5
C7—C8—H8	119.9	O3—C21—H21A	109.5
C9—C8—H8	119.9	O3—C21—H21B	109.5
N1—C9—C8	120.6 (2)	H21A—C21—H21B	109.5
N1—C9—C10	117.2 (2)	O3—C21—H21C	109.5
C8—C9—C10	122.1 (2)	H21A—C21—H21C	109.5
C9—C10—H10A	109.5	H21B—C21—H21C	109.5
C9—C10—H10B	109.5

N1—Zn1—O1—C2	3.23 (14)	C6—C7—C8—C9	0.3 (3)
Br2—Zn1—O1—C2	−108.35 (14)	C1—N1—C9—C8	1.4 (3)
Br1—Zn1—O1—C2	124.58 (13)	Zn1—N1—C9—C8	176.10 (15)
O1—Zn1—N1—C9	−178.0 (2)	C1—N1—C9—C10	−178.93 (19)
Br2—Zn1—N1—C9	−64.7 (2)	Zn1—N1—C9—C10	−4.3 (3)
Br1—Zn1—N1—C9	72.5 (2)	C7—C8—C9—N1	−1.1 (3)
O1—Zn1—N1—C1	−2.90 (14)	C7—C8—C9—C10	179.2 (2)
Br2—Zn1—N1—C1	110.42 (13)	C19—N2—C11—C16	−2.7 (3)
Br1—Zn1—N1—C1	−112.43 (13)	C19—N2—C11—C12	176.3 (2)
C9—N1—C1—C6	−0.9 (3)	N2—C11—C12—O2	0.2 (3)
Zn1—N1—C1—C6	−176.60 (17)	C16—C11—C12—O2	179.15 (19)
C9—N1—C1—C2	177.82 (19)	N2—C11—C12—C13	−179.13 (19)
Zn1—N1—C1—C2	2.1 (2)	C16—C11—C12—C13	−0.2 (3)
Zn1—O1—C2—C3	176.09 (18)	O2—C12—C13—C14	−179.0 (2)
Zn1—O1—C2—C1	−3.1 (2)	C11—C12—C13—C14	0.3 (3)
N1—C1—C2—O1	0.6 (3)	C12—C13—C14—C15	−0.1 (3)
C6—C1—C2—O1	179.3 (2)	C13—C14—C15—C16	−0.3 (3)
N1—C1—C2—C3	−178.6 (2)	N2—C11—C16—C15	178.7 (2)
C6—C1—C2—C3	0.1 (3)	C12—C11—C16—C15	−0.2 (3)
O1—C2—C3—C4	−179.7 (2)	N2—C11—C16—C17	1.1 (3)
C1—C2—C3—C4	−0.6 (3)	C12—C11—C16—C17	−177.8 (2)
C2—C3—C4—C5	0.4 (4)	C14—C15—C16—C11	0.4 (3)
C3—C4—C5—C6	0.3 (4)	C14—C15—C16—C17	177.9 (2)
N1—C1—C6—C5	179.2 (2)	C11—C16—C17—C18	0.8 (3)
C2—C1—C6—C5	0.6 (3)	C15—C16—C17—C18	−176.8 (2)
N1—C1—C6—C7	0.1 (3)	C16—C17—C18—C19	−1.2 (3)
C2—C1—C6—C7	−178.6 (2)	C11—N2—C19—C18	2.2 (3)
C4—C5—C6—C1	−0.7 (3)	C11—N2—C19—C20	−177.2 (2)
C4—C5—C6—C7	178.4 (2)	C17—C18—C19—N2	−0.3 (3)
C1—C6—C7—C8	0.2 (3)	C17—C18—C19—C20	179.1 (2)
C5—C6—C7—C8	−178.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.84	1.71	2.546 (2)	172
O3—H3···Br1ⁱ	0.84	2.48	3.2941 (17)	163
N2—H2n···O3	0.86	1.91	2.739 (3)	162

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	(C₁₀H₁₀NO)[ZnBr₂(C₁₀H₈NO)]·CH₄O
M_r	575.60
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.9704 (8), 13.9954 (11), 15.8815 (12)
β (°)	105.815 (1)
V (Å³)	2132.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.93
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.278, 0.372
No. of measured, independent and observed [I > 2σ(I)] reflections	19908, 4889, 4044
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.057, 1.03
No. of reflections	4889
No. of parameters	267
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.37

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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	1.71	2.546 (2)	172
O3—H3···Br1ⁱ	0.84	2.48	3.2941 (17)	163
N2—H2n···O3	0.86	1.91	2.739 (3)	162

Symmetry code: (i) x−1, y, z.

Acknowledgements

We 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
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. 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. (1996). SADABS. University of Göttingen, Germany. 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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