8-Hy-droxy-2-methyl-quinolinium dibromido(2-methyl-quinolin-8-olato-κN,O)zincate(II) methanol monosolvate.

The anion of the title salt, (C(10)H(10)NO)[ZnBr(2)(C(10)H(8)NO)]·CH(3)OH, has its metal atom N,O-chelated by the deprotonated 2-methyl-8-hy-droxy-quinoline ligand. The hy-droxy unit of the cation is a hydrogen-bond donor to the alkoxide O atom of the tetra-hedrally coordinated anion, whereas the ammonium cation is a hydrogen-bond donor to the methano-lic O atom. In the crystal, adjacent ion pairs and solvent mol-ecules 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 = 575.60

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.057

S = 1.03

4889 reflections

267 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.37 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C10H10NO)[ZnBr2(C10H8NO)]·CH4O	F(000) = 1144
Mr = 575.60	Dx = 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

Bruker SMART APEX diffractometer	4889 independent reflections
Radiation source: fine-focus sealed tube	4044 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.278, Tmax = 0.372	k = −18→18
19908 measured reflections	l = −19→20

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(Fo2) + (0.0224P)2 + 0.8543P] where P = (Fo2 + 2Fc2)/3
4889 reflections	(Δ/σ)max = 0.001
267 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .