Bromido(quinolin-8-ol-κ2N,O)(quinolin-8-olato-κ2N,O)zinc(II) methanol monosolvate

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

doi:10.1107/S160053681003672X

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1278

doi:10.1107/S160053681003672X

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Bromido(quinolin-8-ol-κ²N,O)(quinolin-8-olato-κ²N,O)zinc(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 title compound, [ZnBr(C₉H₆NO)(C₉H₇NO)]·CH₃OH, has its metal atom N,O-chelated by a neutral and a deprotonated 8-hydroxyquinoline ligand. The hydroxy unit of the neutral ligand is a hydrogen-bond donor to the methanol O atom and the alkoxy O atom of the monoanionic ligand is a hydrogen-bond acceptor to the methanol O atom. In the crystal, adjacent molecules are linked by these two hydrogen bonds, generating a chain running along the a axis.

Related literature

For a related structure, see: Najafi et al. (2010 ).

Experimental

Crystal data

[ZnBr(C₉H₆NO)(C₉H₇NO)]·CH₄O
M_r = 466.63
Triclinic, $[P \overline 1]$
a = 8.4485 (7) Å
b = 8.6968 (7) Å
c = 13.1868 (10) Å
α = 97.241 (1)°
β = 99.209 (1)°
γ = 109.470 (1)°
V = 884.81 (12) Å³
Z = 2
Mo Kα radiation
μ = 3.67 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.406, T_max = 0.711
8392 measured reflections
4022 independent reflections
3354 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.103
S = 1.10
4022 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.85 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3ⁱ	0.84	1.90	2.585 (4)	137
O3—H3⋯O1	0.84	1.71	2.551 (4)	178
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/S160053681003672X/bt5356sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681003672X/bt5356Isup2.hkl

checkCIF report

Comment top

An earlier study reported C₁₀H₁₀NO^+.ZnBr₂(C₁₀H₈NO)^.CH₃OH, which feature cations, tetrahedral anions and solvent molecules linked by N···O, O···O and O···Br hydrogen bonds into a linear chain. The salt was synthesized by reacting zinc bromide and 2-methyl-8-hydroxyquinoline in methanol; no base was added (Najafi et al., 2010). The present study uses 8-hydoxyquinoline instead of 2-methy-8-hydroxyquinoline as the organic reactant. The product is a mono-solavated neutral molecule (Scheme I, Fig. 1). The methanol-solvated compound, ZnBr(C₉H₆NO)(C₉H₇NO)^.CH₃OH, has its metal atom N,O-chelated by a neutral and deprotonated 8-hydroxyquinoline ligand. The hydroxy unit of the neutral ligand is hydrogen-bond donor methanol O atom and the alkoxy O atom of the monoanionic ligand is hydrogen-bond acceptor to methanol O atom. Adjacent molecules are linked by these two hydrogen bonds to generate a linear chain running along the a-axis of the triclinic unit cell (Fig. 2).

Related literature top

For a related structure, see: Najafi et al. (2010).

Experimental top

Zinc bromide (0.19 g, 0.75 mmol) and 8-hydroxyquinoline (0.22 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.
	Fig. 2. Hydrogen bonded chain structure.

Bromido(quinolin-8-ol-κ²N,O)(quinolin-8-olato- κ²N,O)zinc(II) methanol monosolvate top

Crystal data top

[ZnBr(C₉H₆NO)(C₉H₇NO)]·CH₄O	Z = 2
M_r = 466.63	F(000) = 468
Triclinic, P1	D_x = 1.751 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4485 (7) Å	Cell parameters from 3867 reflections
b = 8.6968 (7) Å	θ = 2.5–28.2°
c = 13.1868 (10) Å	µ = 3.67 mm⁻¹
α = 97.241 (1)°	T = 100 K
β = 99.209 (1)°	Prism, yellow
γ = 109.470 (1)°	0.30 × 0.20 × 0.10 mm
V = 884.81 (12) Å³

Data collection top

Bruker SMART APEX diffractometer	4022 independent reflections
Radiation source: fine-focus sealed tube	3354 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.406, T_max = 0.711	k = −11→11
8392 measured reflections	l = −15→17

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0457P)² + 1.9422P] where P = (F_o² + 2F_c²)/3
4022 reflections	(Δ/σ)_max = 0.001
237 parameters	Δρ_max = 0.78 e Å⁻³
0 restraints	Δρ_min = −0.85 e Å⁻³

Crystal data top

[ZnBr(C₉H₆NO)(C₉H₇NO)]·CH₄O	γ = 109.470 (1)°
M_r = 466.63	V = 884.81 (12) Å³
Triclinic, P1	Z = 2
a = 8.4485 (7) Å	Mo Kα radiation
b = 8.6968 (7) Å	µ = 3.67 mm⁻¹
c = 13.1868 (10) Å	T = 100 K
α = 97.241 (1)°	0.30 × 0.20 × 0.10 mm
β = 99.209 (1)°

Data collection top

Bruker SMART APEX diffractometer	4022 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3354 reflections with I > 2σ(I)
T_min = 0.406, T_max = 0.711	R_int = 0.028
8392 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.10	Δρ_max = 0.78 e Å⁻³
4022 reflections	Δρ_min = −0.85 e Å⁻³
237 parameters

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

	x	y	z	U_iso*/U_eq
Zn1	0.45338 (5)	0.64466 (5)	0.71737 (3)	0.01184 (12)
Br1	0.58054 (4)	0.92415 (4)	0.81357 (3)	0.01654 (11)
O1	0.6864 (3)	0.6465 (3)	0.64187 (19)	0.0152 (5)
O2	0.2092 (3)	0.5306 (3)	0.73396 (19)	0.0145 (5)
H2	0.1230	0.5461	0.7024	0.022*
O3	0.9908 (3)	0.6800 (3)	0.7299 (2)	0.0209 (6)
H3	0.8908	0.6707	0.7016	0.031*
N1	0.3868 (4)	0.6687 (4)	0.5653 (2)	0.0119 (6)
N2	0.5025 (4)	0.4869 (3)	0.8093 (2)	0.0121 (6)
C1	0.5180 (4)	0.7280 (4)	0.5148 (3)	0.0110 (6)
C2	0.6796 (4)	0.7212 (4)	0.5573 (3)	0.0128 (7)
C3	0.8163 (4)	0.7842 (4)	0.5120 (3)	0.0150 (7)
H3A	0.9255	0.7819	0.5415	0.018*
C4	0.7946 (5)	0.8531 (5)	0.4209 (3)	0.0177 (7)
H4	0.8897	0.8950	0.3892	0.021*
C5	0.6384 (4)	0.8603 (4)	0.3777 (3)	0.0151 (7)
H5	0.6264	0.9080	0.3172	0.018*
C6	0.4957 (5)	0.7963 (4)	0.4238 (3)	0.0141 (7)
C7	0.3290 (5)	0.7915 (4)	0.3821 (3)	0.0153 (7)
H7	0.3085	0.8350	0.3208	0.018*
C8	0.1969 (5)	0.7238 (5)	0.4304 (3)	0.0173 (7)
H8	0.0835	0.7166	0.4020	0.021*
C9	0.2328 (4)	0.6652 (4)	0.5232 (3)	0.0156 (7)
H9	0.1412	0.6208	0.5571	0.019*
C10	0.3596 (4)	0.4025 (4)	0.8429 (3)	0.0109 (6)
C11	0.2035 (4)	0.4283 (4)	0.8012 (3)	0.0138 (7)
C12	0.0569 (4)	0.3427 (4)	0.8339 (3)	0.0150 (7)
H12	−0.0481	0.3560	0.8074	0.018*
C13	0.0599 (5)	0.2365 (5)	0.9055 (3)	0.0165 (7)
H13	−0.0433	0.1800	0.9263	0.020*
C14	0.2083 (5)	0.2119 (4)	0.9464 (3)	0.0165 (7)
H14	0.2079	0.1400	0.9951	0.020*
C15	0.3606 (4)	0.2956 (4)	0.9146 (3)	0.0128 (7)
C16	0.5206 (5)	0.2803 (4)	0.9519 (3)	0.0145 (7)
H16	0.5282	0.2085	0.9996	0.017*
C17	0.6636 (5)	0.3682 (4)	0.9194 (3)	0.0153 (7)
H17	0.7716	0.3604	0.9457	0.018*
C18	0.6497 (4)	0.4706 (4)	0.8467 (3)	0.0134 (7)
H18	0.7494	0.5301	0.8235	0.016*
C19	1.0704 (5)	0.8335 (5)	0.8036 (3)	0.0271 (9)
H19A	1.0933	0.8107	0.8743	0.041*
H19B	0.9936	0.8967	0.8004	0.041*
H19C	1.1789	0.8984	0.7867	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0117 (2)	0.0145 (2)	0.0111 (2)	0.00508 (15)	0.00377 (15)	0.00635 (15)
Br1	0.0208 (2)	0.01368 (17)	0.01481 (19)	0.00510 (14)	0.00314 (14)	0.00568 (13)
O1	0.0162 (12)	0.0189 (12)	0.0138 (12)	0.0078 (10)	0.0056 (10)	0.0078 (10)
O2	0.0105 (11)	0.0194 (12)	0.0163 (13)	0.0080 (10)	0.0012 (9)	0.0076 (10)
O3	0.0130 (12)	0.0228 (13)	0.0256 (15)	0.0072 (11)	−0.0002 (11)	0.0035 (11)
N1	0.0106 (13)	0.0158 (14)	0.0101 (14)	0.0054 (11)	0.0026 (11)	0.0030 (11)
N2	0.0159 (14)	0.0129 (13)	0.0080 (13)	0.0037 (11)	0.0045 (11)	0.0049 (11)
C1	0.0104 (15)	0.0115 (15)	0.0109 (16)	0.0041 (12)	0.0033 (12)	−0.0001 (12)
C2	0.0159 (17)	0.0138 (15)	0.0117 (16)	0.0083 (13)	0.0044 (13)	0.0042 (13)
C3	0.0115 (16)	0.0187 (17)	0.0171 (18)	0.0080 (13)	0.0034 (13)	0.0043 (14)
C4	0.0172 (18)	0.0193 (17)	0.0155 (18)	0.0026 (14)	0.0076 (14)	0.0052 (14)
C5	0.0169 (17)	0.0161 (16)	0.0107 (16)	0.0044 (14)	0.0015 (13)	0.0030 (13)
C6	0.0185 (17)	0.0126 (15)	0.0114 (16)	0.0046 (13)	0.0061 (14)	0.0027 (13)
C7	0.0180 (17)	0.0180 (17)	0.0099 (16)	0.0072 (14)	−0.0003 (13)	0.0043 (13)
C8	0.0159 (17)	0.0236 (18)	0.0126 (17)	0.0076 (14)	0.0010 (14)	0.0061 (14)
C9	0.0120 (16)	0.0209 (17)	0.0161 (18)	0.0077 (14)	0.0045 (14)	0.0045 (14)
C10	0.0124 (15)	0.0120 (15)	0.0089 (15)	0.0056 (12)	0.0025 (12)	0.0011 (12)
C11	0.0145 (16)	0.0158 (16)	0.0118 (16)	0.0062 (13)	0.0025 (13)	0.0034 (13)
C12	0.0108 (16)	0.0208 (17)	0.0123 (17)	0.0054 (13)	0.0003 (13)	0.0038 (13)
C13	0.0146 (17)	0.0199 (17)	0.0152 (18)	0.0041 (14)	0.0063 (14)	0.0062 (14)
C14	0.0206 (18)	0.0153 (16)	0.0152 (18)	0.0056 (14)	0.0069 (14)	0.0066 (14)
C15	0.0151 (16)	0.0123 (15)	0.0082 (16)	0.0029 (13)	0.0004 (13)	−0.0002 (12)
C16	0.0197 (18)	0.0145 (16)	0.0127 (17)	0.0105 (14)	0.0021 (14)	0.0048 (13)
C17	0.0143 (17)	0.0208 (17)	0.0127 (17)	0.0093 (14)	0.0009 (13)	0.0043 (14)
C18	0.0121 (16)	0.0171 (16)	0.0143 (17)	0.0081 (13)	0.0049 (13)	0.0045 (13)
C19	0.0193 (19)	0.027 (2)	0.029 (2)	0.0051 (16)	0.0007 (17)	−0.0014 (17)

Geometric parameters (Å, º) top

Zn1—O2	2.030 (2)	C7—C8	1.372 (5)
Zn1—N2	2.040 (3)	C7—H7	0.9500
Zn1—N1	2.050 (3)	C8—C9	1.411 (5)
Zn1—O1	2.340 (2)	C8—H8	0.9500
Zn1—Br1	2.3911 (5)	C9—H9	0.9500
O1—C2	1.362 (4)	C10—C15	1.409 (5)
O2—C11	1.328 (4)	C10—C11	1.445 (5)
O2—H2	0.8400	C11—C12	1.383 (5)
O3—C19	1.430 (5)	C12—C13	1.404 (5)
O3—H3	0.8400	C12—H12	0.9500
N1—C9	1.319 (4)	C13—C14	1.378 (5)
N1—C1	1.372 (4)	C13—H13	0.9500
N2—C18	1.322 (4)	C14—C15	1.410 (5)
N2—C10	1.361 (4)	C14—H14	0.9500
C1—C2	1.414 (5)	C15—C16	1.417 (5)
C1—C6	1.418 (5)	C16—C17	1.364 (5)
C2—C3	1.368 (5)	C16—H16	0.9500
C3—C4	1.422 (5)	C17—C18	1.406 (5)
C3—H3A	0.9500	C17—H17	0.9500
C4—C5	1.376 (5)	C18—H18	0.9500
C4—H4	0.9500	C19—H19A	0.9800
C5—C6	1.416 (5)	C19—H19B	0.9800
C5—H5	0.9500	C19—H19C	0.9800
C6—C7	1.412 (5)

O2—Zn1—N2	82.51 (11)	C6—C7—H7	120.1
O2—Zn1—N1	95.88 (11)	C7—C8—C9	118.8 (3)
N2—Zn1—N1	143.75 (11)	C7—C8—H8	120.6
O2—Zn1—O1	150.98 (10)	C9—C8—H8	120.6
N2—Zn1—O1	90.06 (10)	N1—C9—C8	123.4 (3)
N1—Zn1—O1	73.91 (10)	N1—C9—H9	118.3
O2—Zn1—Br1	112.41 (7)	C8—C9—H9	118.3
N2—Zn1—Br1	109.66 (8)	N2—C10—C15	122.9 (3)
N1—Zn1—Br1	104.40 (8)	N2—C10—C11	116.5 (3)
O1—Zn1—Br1	96.52 (6)	C15—C10—C11	120.7 (3)
C2—O1—Zn1	108.4 (2)	O2—C11—C12	124.4 (3)
C11—O2—Zn1	111.3 (2)	O2—C11—C10	118.4 (3)
C11—O2—H2	124.4	C12—C11—C10	117.2 (3)
Zn1—O2—H2	124.4	C11—C12—C13	121.4 (3)
C19—O3—H3	109.5	C11—C12—H12	119.3
C9—N1—C1	118.4 (3)	C13—C12—H12	119.3
C9—N1—Zn1	122.8 (2)	C14—C13—C12	121.9 (3)
C1—N1—Zn1	117.2 (2)	C14—C13—H13	119.0
C18—N2—C10	119.0 (3)	C12—C13—H13	119.0
C18—N2—Zn1	129.8 (2)	C13—C14—C15	118.6 (3)
C10—N2—Zn1	110.8 (2)	C13—C14—H14	120.7
N1—C1—C2	117.6 (3)	C15—C14—H14	120.7
N1—C1—C6	122.0 (3)	C10—C15—C14	120.1 (3)
C2—C1—C6	120.3 (3)	C10—C15—C16	116.4 (3)
O1—C2—C3	124.0 (3)	C14—C15—C16	123.5 (3)
O1—C2—C1	116.0 (3)	C17—C16—C15	120.2 (3)
C3—C2—C1	119.9 (3)	C17—C16—H16	119.9
C2—C3—C4	119.9 (3)	C15—C16—H16	119.9
C2—C3—H3A	120.0	C16—C17—C18	119.3 (3)
C4—C3—H3A	120.0	C16—C17—H17	120.4
C5—C4—C3	121.2 (3)	C18—C17—H17	120.4
C5—C4—H4	119.4	N2—C18—C17	122.2 (3)
C3—C4—H4	119.4	N2—C18—H18	118.9
C4—C5—C6	119.7 (3)	C17—C18—H18	118.9
C4—C5—H5	120.2	O3—C19—H19A	109.5
C6—C5—H5	120.2	O3—C19—H19B	109.5
C7—C6—C5	123.5 (3)	H19A—C19—H19B	109.5
C7—C6—C1	117.5 (3)	O3—C19—H19C	109.5
C5—C6—C1	118.9 (3)	H19A—C19—H19C	109.5
C8—C7—C6	119.8 (3)	H19B—C19—H19C	109.5
C8—C7—H7	120.1

O2—Zn1—O1—C2	94.6 (3)	C4—C5—C6—C7	−177.0 (3)
N2—Zn1—O1—C2	169.1 (2)	C4—C5—C6—C1	0.9 (5)
N1—Zn1—O1—C2	22.0 (2)	N1—C1—C6—C7	−4.1 (5)
Br1—Zn1—O1—C2	−81.1 (2)	C2—C1—C6—C7	176.7 (3)
N2—Zn1—O2—C11	6.3 (2)	N1—C1—C6—C5	177.9 (3)
N1—Zn1—O2—C11	149.9 (2)	C2—C1—C6—C5	−1.3 (5)
O1—Zn1—O2—C11	82.7 (3)	C5—C6—C7—C8	178.5 (3)
Br1—Zn1—O2—C11	−101.9 (2)	C1—C6—C7—C8	0.6 (5)
O2—Zn1—N1—C9	21.6 (3)	C6—C7—C8—C9	2.0 (5)
N2—Zn1—N1—C9	106.9 (3)	C1—N1—C9—C8	−1.9 (5)
O1—Zn1—N1—C9	173.8 (3)	Zn1—N1—C9—C8	162.7 (3)
Br1—Zn1—N1—C9	−93.4 (3)	C7—C8—C9—N1	−1.4 (6)
O2—Zn1—N1—C1	−173.6 (2)	C18—N2—C10—C15	−1.2 (5)
N2—Zn1—N1—C1	−88.3 (3)	Zn1—N2—C10—C15	−174.5 (3)
O1—Zn1—N1—C1	−21.3 (2)	C18—N2—C10—C11	178.6 (3)
Br1—Zn1—N1—C1	71.4 (2)	Zn1—N2—C10—C11	5.2 (4)
O2—Zn1—N2—C18	−178.6 (3)	Zn1—O2—C11—C12	175.2 (3)
N1—Zn1—N2—C18	91.6 (3)	Zn1—O2—C11—C10	−5.4 (4)
O1—Zn1—N2—C18	29.5 (3)	N2—C10—C11—O2	0.1 (5)
Br1—Zn1—N2—C18	−67.5 (3)	C15—C10—C11—O2	179.8 (3)
O2—Zn1—N2—C10	−6.2 (2)	N2—C10—C11—C12	179.6 (3)
N1—Zn1—N2—C10	−96.0 (3)	C15—C10—C11—C12	−0.7 (5)
O1—Zn1—N2—C10	−158.1 (2)	O2—C11—C12—C13	−179.9 (3)
Br1—Zn1—N2—C10	104.9 (2)	C10—C11—C12—C13	0.7 (5)
C9—N1—C1—C2	−176.1 (3)	C11—C12—C13—C14	−0.2 (6)
Zn1—N1—C1—C2	18.4 (4)	C12—C13—C14—C15	−0.3 (5)
C9—N1—C1—C6	4.7 (5)	N2—C10—C15—C14	179.9 (3)
Zn1—N1—C1—C6	−160.8 (3)	C11—C10—C15—C14	0.2 (5)
Zn1—O1—C2—C3	161.4 (3)	N2—C10—C15—C16	0.5 (5)
Zn1—O1—C2—C1	−20.0 (3)	C11—C10—C15—C16	−179.2 (3)
N1—C1—C2—O1	3.7 (4)	C13—C14—C15—C10	0.3 (5)
C6—C1—C2—O1	−177.1 (3)	C13—C14—C15—C16	179.7 (3)
N1—C1—C2—C3	−177.7 (3)	C10—C15—C16—C17	1.0 (5)
C6—C1—C2—C3	1.6 (5)	C14—C15—C16—C17	−178.5 (3)
O1—C2—C3—C4	177.1 (3)	C15—C16—C17—C18	−1.7 (5)
C1—C2—C3—C4	−1.4 (5)	C10—N2—C18—C17	0.4 (5)
C2—C3—C4—C5	1.0 (6)	Zn1—N2—C18—C17	172.3 (3)
C3—C4—C5—C6	−0.8 (5)	C16—C17—C18—N2	1.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.84	1.90	2.585 (4)	137
O3—H3···O1	0.84	1.71	2.551 (4)	178

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[ZnBr(C₉H₆NO)(C₉H₇NO)]·CH₄O
M_r	466.63
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.4485 (7), 8.6968 (7), 13.1868 (10)
α, β, γ (°)	97.241 (1), 99.209 (1), 109.470 (1)
V (Å³)	884.81 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.67
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.406, 0.711
No. of measured, independent and observed [I > 2σ(I)] reflections	8392, 4022, 3354
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.103, 1.10
No. of reflections	4022
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.85

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···O3ⁱ	0.84	1.90	2.585 (4)	137
O3—H3···O1	0.84	1.71	2.551 (4)	178

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
Najafi, E., Amini, M. M. & Ng, S. W. (2010). Acta Cryst. E66, m1276. 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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