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

The anion of the title salt, (C(10)H(10)NO)[Zn(C(10)H(8)NO)I(2)]·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 acts as 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⋯I 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)[Zn(C10H8NO)I2]·CH4O

M = 669.58

Monoclinic,

a = 10.1745 (6) Å

b = 14.6292 (9) Å

c = 16.5321 (10) Å

β = 106.356 (1)°

V = 2361.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 3.68 mm−1

T = 295 K

0.35 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.359, T max = 0.608

21863 measured reflections

5404 independent reflections

4049 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.090

S = 1.06

5404 reflections

267 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.78 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/S1600536810036718/bt5355sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036718/bt5355Isup2.hkl

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

(C10H10NO)[Zn(C10H8NO)I2]·CH4O	F(000) = 1288
Mr = 669.58	Dx = 1.884 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6864 reflections
a = 10.1745 (6) Å	θ = 2.5–25.1°
b = 14.6292 (9) Å	µ = 3.68 mm−1
c = 16.5321 (10) Å	T = 295 K
β = 106.356 (1)°	Triangular block, yellow
V = 2361.1 (2) Å3	0.35 × 0.25 × 0.15 mm
Z = 4

Bruker SMART APEX diffractometer	5404 independent reflections
Radiation source: fine-focus sealed tube	4049 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.359, Tmax = 0.608	k = −19→19
21863 measured reflections	l = −21→18

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0352P)2 + 2.9232P] where P = (Fo2 + 2Fc2)/3
5404 reflections	(Δ/σ)max = 0.001
267 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.78 e Å−3

	x	y	z	Uiso*/Ueq
I1	0.99864 (3)	0.22364 (2)	0.185681 (19)	0.05940 (11)
I2	1.12403 (4)	0.50224 (2)	0.22894 (2)	0.06773 (12)
Zn1	0.98601 (5)	0.37087 (4)	0.26758 (3)	0.04947 (13)
O1	0.7946 (3)	0.4058 (2)	0.25987 (17)	0.0590 (8)
O2	0.5880 (3)	0.3620 (2)	0.13701 (17)	0.0575 (8)
H2	0.6556	0.3798	0.1736	0.086*
O3	0.3218 (4)	0.2893 (5)	0.1583 (3)	0.132 (2)
H3	0.2424	0.3008	0.1573	0.198*
N1	1.0064 (3)	0.3664 (2)	0.39435 (19)	0.0421 (7)
N2	0.3603 (3)	0.3482 (2)	0.0082 (2)	0.0464 (8)
H2N	0.3620	0.3346	0.0591	0.056*
C1	0.8857 (4)	0.3933 (3)	0.4085 (2)	0.0439 (9)
C2	0.7747 (4)	0.4140 (3)	0.3364 (2)	0.0491 (10)
C3	0.6530 (5)	0.4435 (3)	0.3495 (3)	0.0585 (11)
H3a	0.5794	0.4587	0.3036	0.070*
C4	0.6399 (5)	0.4505 (4)	0.4314 (3)	0.0675 (13)
H4	0.5568	0.4699	0.4386	0.081*
C5	0.7444 (5)	0.4301 (3)	0.5007 (3)	0.0639 (13)
H5	0.7325	0.4350	0.5543	0.077*
C6	0.8711 (5)	0.4016 (3)	0.4906 (3)	0.0507 (10)
C7	0.9878 (5)	0.3799 (3)	0.5575 (3)	0.0611 (13)
H7	0.9831	0.3834	0.6128	0.073*
C8	1.1066 (5)	0.3541 (3)	0.5424 (3)	0.0585 (12)
H8	1.1828	0.3407	0.5872	0.070*
C9	1.1151 (4)	0.3477 (3)	0.4589 (2)	0.0481 (9)
C10	1.2444 (5)	0.3205 (3)	0.4395 (3)	0.0625 (12)
H10A	1.2797	0.3717	0.4159	0.094*
H10B	1.2260	0.2710	0.3998	0.094*
H10C	1.3107	0.3014	0.4904	0.094*
C11	0.4800 (4)	0.3758 (3)	−0.0072 (2)	0.0423 (8)
C12	0.6010 (4)	0.3837 (3)	0.0609 (2)	0.0445 (9)
C13	0.7190 (4)	0.4124 (3)	0.0438 (3)	0.0487 (9)
H13	0.7998	0.4173	0.0873	0.058*
C14	0.7184 (5)	0.4343 (3)	−0.0388 (3)	0.0558 (11)
H14	0.7991	0.4541	−0.0488	0.067*
C15	0.6026 (5)	0.4273 (3)	−0.1051 (3)	0.0548 (11)
H15	0.6049	0.4417	−0.1594	0.066*
C16	0.4804 (4)	0.3981 (3)	−0.0899 (2)	0.0461 (9)
C17	0.3539 (5)	0.3907 (3)	−0.1537 (3)	0.0564 (11)
H17	0.3501	0.4049	−0.2091	0.068*
C18	0.2383 (5)	0.3632 (3)	−0.1349 (3)	0.0571 (11)
H18	0.1564	0.3588	−0.1776	0.069*
C19	0.2415 (4)	0.3414 (3)	−0.0518 (3)	0.0542 (11)
C20	0.1160 (5)	0.3133 (4)	−0.0273 (4)	0.0782 (16)
H20A	0.1130	0.3455	0.0227	0.117*
H20B	0.1189	0.2487	−0.0168	0.117*
H20C	0.0358	0.3277	−0.0723	0.117*
C21	0.3972 (6)	0.2771 (4)	0.2385 (3)	0.0768 (15)
H21A	0.4920	0.2717	0.2404	0.115*
H21B	0.3680	0.2224	0.2605	0.115*
H21C	0.3853	0.3286	0.2718	0.115*

	U11	U22	U33	U12	U13	U23
I1	0.06369 (19)	0.0647 (2)	0.04850 (17)	−0.01375 (14)	0.01360 (13)	−0.00404 (13)
I2	0.0790 (2)	0.0597 (2)	0.0736 (2)	−0.00371 (16)	0.03639 (18)	0.00974 (15)
Zn1	0.0457 (3)	0.0681 (3)	0.0332 (2)	−0.0018 (2)	0.00879 (19)	0.0042 (2)
O1	0.0437 (16)	0.099 (2)	0.0323 (14)	0.0011 (16)	0.0070 (12)	0.0026 (15)
O2	0.0492 (17)	0.085 (2)	0.0346 (15)	−0.0055 (16)	0.0053 (12)	0.0056 (15)
O3	0.058 (2)	0.279 (7)	0.061 (3)	0.008 (3)	0.022 (2)	0.046 (3)
N1	0.0462 (18)	0.0456 (18)	0.0308 (15)	−0.0052 (14)	0.0046 (13)	0.0035 (13)
N2	0.0467 (19)	0.0472 (19)	0.0412 (18)	0.0031 (15)	0.0057 (15)	0.0036 (15)
C1	0.052 (2)	0.045 (2)	0.0345 (19)	−0.0133 (17)	0.0110 (17)	0.0016 (16)
C2	0.048 (2)	0.061 (3)	0.039 (2)	−0.0094 (19)	0.0128 (18)	0.0015 (18)
C3	0.054 (3)	0.067 (3)	0.055 (3)	−0.003 (2)	0.016 (2)	0.003 (2)
C4	0.063 (3)	0.079 (3)	0.070 (3)	−0.005 (3)	0.034 (3)	−0.011 (3)
C5	0.083 (4)	0.067 (3)	0.051 (3)	−0.012 (3)	0.034 (3)	−0.006 (2)
C6	0.070 (3)	0.045 (2)	0.038 (2)	−0.013 (2)	0.018 (2)	0.0007 (17)
C7	0.092 (4)	0.060 (3)	0.030 (2)	−0.016 (3)	0.015 (2)	0.0013 (19)
C8	0.075 (3)	0.054 (3)	0.036 (2)	−0.005 (2)	−0.001 (2)	0.0066 (19)
C9	0.057 (2)	0.043 (2)	0.039 (2)	−0.0060 (18)	0.0048 (18)	0.0027 (17)
C10	0.060 (3)	0.065 (3)	0.052 (3)	0.003 (2)	0.000 (2)	0.003 (2)
C11	0.047 (2)	0.038 (2)	0.040 (2)	0.0055 (16)	0.0097 (17)	−0.0019 (16)
C12	0.049 (2)	0.048 (2)	0.036 (2)	0.0058 (17)	0.0106 (17)	0.0007 (16)
C13	0.042 (2)	0.057 (2)	0.044 (2)	0.0040 (18)	0.0080 (17)	−0.0008 (19)
C14	0.056 (3)	0.059 (3)	0.057 (3)	0.003 (2)	0.024 (2)	−0.001 (2)
C15	0.066 (3)	0.059 (3)	0.043 (2)	0.010 (2)	0.019 (2)	0.0031 (19)
C16	0.055 (2)	0.044 (2)	0.038 (2)	0.0074 (18)	0.0093 (18)	−0.0044 (16)
C17	0.069 (3)	0.058 (3)	0.036 (2)	0.009 (2)	0.005 (2)	−0.0038 (19)
C18	0.053 (3)	0.063 (3)	0.047 (2)	0.004 (2)	−0.001 (2)	−0.006 (2)
C19	0.049 (2)	0.051 (2)	0.054 (3)	0.0018 (19)	0.000 (2)	0.001 (2)
C20	0.050 (3)	0.098 (4)	0.079 (4)	−0.011 (3)	0.006 (3)	0.014 (3)
C21	0.078 (4)	0.085 (4)	0.069 (3)	0.002 (3)	0.022 (3)	0.023 (3)

I1—Zn1	2.5665 (6)	C8—H8	0.9300
I2—Zn1	2.5649 (6)	C9—C10	1.493 (6)
Zn1—O1	1.982 (3)	C10—H10A	0.9600
Zn1—N1	2.048 (3)	C10—H10B	0.9600
O1—C2	1.341 (5)	C10—H10C	0.9600
O2—C12	1.340 (5)	C11—C16	1.407 (5)
O2—H2	0.8200	C11—C12	1.419 (5)
O3—C21	1.343 (6)	C12—C13	1.375 (6)
O3—H3	0.8200	C13—C14	1.400 (6)
N1—C9	1.331 (5)	C13—H13	0.9300
N1—C1	1.371 (5)	C14—C15	1.369 (6)
N2—C19	1.333 (5)	C14—H14	0.9300
N2—C11	1.373 (5)	C15—C16	1.402 (6)
N2—H2N	0.8600	C15—H15	0.9300
C1—C6	1.412 (5)	C16—C17	1.420 (6)
C1—C2	1.425 (6)	C17—C18	1.359 (7)
C2—C3	1.385 (6)	C17—H17	0.9300
C3—C4	1.402 (7)	C18—C19	1.403 (6)
C3—H3a	0.9300	C18—H18	0.9300
C4—C5	1.359 (7)	C19—C20	1.502 (7)
C4—H4	0.9300	C20—H20A	0.9600
C5—C6	1.409 (7)	C20—H20B	0.9600
C5—H5	0.9300	C20—H20C	0.9600
C6—C7	1.412 (6)	C21—H21A	0.9600
C7—C8	1.354 (7)	C21—H21B	0.9600
C7—H7	0.9300	C21—H21C	0.9600
C8—C9	1.410 (6)
O1—Zn1—N1	83.61 (12)	H10A—C10—H10B	109.5
O1—Zn1—I2	112.82 (10)	C9—C10—H10C	109.5
N1—Zn1—I2	111.95 (9)	H10A—C10—H10C	109.5
O1—Zn1—I1	112.11 (10)	H10B—C10—H10C	109.5
N1—Zn1—I1	120.50 (9)	N2—C11—C16	119.6 (4)
I2—Zn1—I1	112.65 (2)	N2—C11—C12	119.6 (3)
C2—O1—Zn1	111.6 (2)	C16—C11—C12	120.8 (4)
C12—O2—H2	109.5	O2—C12—C13	126.1 (4)
C21—O3—H3	109.5	O2—C12—C11	115.6 (4)
C9—N1—C1	120.2 (3)	C13—C12—C11	118.3 (4)
C9—N1—Zn1	130.5 (3)	C12—C13—C14	120.4 (4)
C1—N1—Zn1	109.2 (2)	C12—C13—H13	119.8
C19—N2—C11	123.4 (4)	C14—C13—H13	119.8
C19—N2—H2N	118.3	C15—C14—C13	122.0 (4)
C11—N2—H2N	118.3	C15—C14—H14	119.0
N1—C1—C6	122.1 (4)	C13—C14—H14	119.0
N1—C1—C2	117.1 (3)	C14—C15—C16	119.1 (4)
C6—C1—C2	120.9 (4)	C14—C15—H15	120.5
O1—C2—C3	123.7 (4)	C16—C15—H15	120.5
O1—C2—C1	118.4 (4)	C15—C16—C11	119.3 (4)
C3—C2—C1	117.9 (4)	C15—C16—C17	123.7 (4)
C2—C3—C4	120.5 (4)	C11—C16—C17	117.0 (4)
C2—C3—H3a	119.8	C18—C17—C16	121.0 (4)
C4—C3—H3a	119.8	C18—C17—H17	119.5
C5—C4—C3	122.2 (5)	C16—C17—H17	119.5
C5—C4—H4	118.9	C17—C18—C19	120.5 (4)
C3—C4—H4	118.9	C17—C18—H18	119.7
C4—C5—C6	119.4 (4)	C19—C18—H18	119.7
C4—C5—H5	120.3	N2—C19—C18	118.5 (4)
C6—C5—H5	120.3	N2—C19—C20	118.8 (4)
C7—C6—C5	124.7 (4)	C18—C19—C20	122.6 (4)
C7—C6—C1	116.1 (4)	C19—C20—H20A	109.5
C5—C6—C1	119.1 (4)	C19—C20—H20B	109.5
C8—C7—C6	121.0 (4)	H20A—C20—H20B	109.5
C8—C7—H7	119.5	C19—C20—H20C	109.5
C6—C7—H7	119.5	H20A—C20—H20C	109.5
C7—C8—C9	120.2 (4)	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	120.3 (4)	H21A—C21—H21B	109.5
N1—C9—C10	117.8 (4)	O3—C21—H21C	109.5
C8—C9—C10	121.9 (4)	H21A—C21—H21C	109.5
C9—C10—H10A	109.5	H21B—C21—H21C	109.5
C9—C10—H10B	109.5
N1—Zn1—O1—C2	3.3 (3)	C6—C7—C8—C9	−0.6 (7)
I2—Zn1—O1—C2	−107.9 (3)	C1—N1—C9—C8	0.8 (6)
I1—Zn1—O1—C2	123.7 (3)	Zn1—N1—C9—C8	176.2 (3)
O1—Zn1—N1—C9	−178.9 (4)	C1—N1—C9—C10	−178.8 (4)
I2—Zn1—N1—C9	−66.8 (4)	Zn1—N1—C9—C10	−3.4 (6)
I1—Zn1—N1—C9	69.2 (4)	C7—C8—C9—N1	−0.3 (6)
O1—Zn1—N1—C1	−3.1 (3)	C7—C8—C9—C10	179.3 (4)
I2—Zn1—N1—C1	109.0 (2)	C19—N2—C11—C16	−0.3 (6)
I1—Zn1—N1—C1	−115.0 (2)	C19—N2—C11—C12	178.1 (4)
C9—N1—C1—C6	−0.4 (6)	N2—C11—C12—O2	0.6 (5)
Zn1—N1—C1—C6	−176.7 (3)	C16—C11—C12—O2	179.0 (4)
C9—N1—C1—C2	178.7 (4)	N2—C11—C12—C13	−179.4 (4)
Zn1—N1—C1—C2	2.4 (4)	C16—C11—C12—C13	−1.0 (6)
Zn1—O1—C2—C3	175.7 (4)	O2—C12—C13—C14	−179.1 (4)
Zn1—O1—C2—C1	−2.9 (5)	C11—C12—C13—C14	0.9 (6)
N1—C1—C2—O1	0.3 (6)	C12—C13—C14—C15	−0.7 (7)
C6—C1—C2—O1	179.4 (4)	C13—C14—C15—C16	0.6 (7)
N1—C1—C2—C3	−178.4 (4)	C14—C15—C16—C11	−0.7 (6)
C6—C1—C2—C3	0.7 (6)	C14—C15—C16—C17	178.4 (4)
O1—C2—C3—C4	−179.9 (4)	N2—C11—C16—C15	179.3 (4)
C1—C2—C3—C4	−1.3 (7)	C12—C11—C16—C15	0.9 (6)
C2—C3—C4—C5	0.7 (8)	N2—C11—C16—C17	0.2 (6)
C3—C4—C5—C6	0.6 (8)	C12—C11—C16—C17	−178.2 (4)
C4—C5—C6—C7	178.9 (5)	C15—C16—C17—C18	−179.1 (4)
C4—C5—C6—C1	−1.1 (7)	C11—C16—C17—C18	0.0 (6)
N1—C1—C6—C7	−0.5 (6)	C16—C17—C18—C19	−0.1 (7)
C2—C1—C6—C7	−179.6 (4)	C11—N2—C19—C18	0.2 (6)
N1—C1—C6—C5	179.6 (4)	C11—N2—C19—C20	−178.1 (4)
C2—C1—C6—C5	0.5 (6)	C17—C18—C19—N2	0.0 (7)
C5—C6—C7—C8	−179.1 (4)	C17—C18—C19—C20	178.2 (5)
C1—C6—C7—C8	1.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82	1.74	2.559 (4)	172
O3—H3···I1i	0.82	2.88	3.575 (4)	144
N2—H2n···O3	0.86	1.92	2.757 (5)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.82	1.74	2.559 (4)	172
O3—H3⋯I1i	0.82	2.88	3.575 (4)	144
N2—H2n⋯O3	0.86	1.92	2.757 (5)	165

Symmetry code: (i) .