catena-Poly[bis-[dimeth-yl(pyridine-κN)indium(III)]-μ4-benzene-1,3-diolato-bis-[di-methyl-indium(III)]-μ4-benzene-1,3-diolato].

The title compound, [In2(CH3)4(C6H4O2)(C5H5N)] or [{(CH3)2In}(1,3-O2C6H4){In(CH3)2(py)}] n , (py = pyridine) contains two crystallographically unique In(III) ions which are in distorted tetra-hedral C2O2 and distorted trigonal-bipyramidal C2O2N coordination environments. The In(III) coordination centers are bridged head-to-head via In-O bonds, yielding four-membered In2O2 rings and zigzag polymeric chains along [001].

Related literature

For background to di­methyl­indium aryl­oxides, see: Briand et al. (2010 ▶); Beachley et al. (2003 ▶); Hausslein et al. (1999 ▶); Blake et al. (2011 ▶); Bradley et al. (1988 ▶); Trentler et al. (1997 ▶). For di­methyl­n class="Chemical">indium compounds with bidentate imine-alkoxide ligands, see: Hu et al. (1999 ▶); Wu et al. (1999 ▶); Pal et al. (2013 ▶); Lewinski et al. (2003 ▶); Ghoshal et al. (2007 ▶).

Experimental

Crystal data

[In2(CH3)4(C6H4O2)(n class="Chemical">C5H5N)]

M = 476.97

Monoclinic,

a = 9.1584 (17) Å

b = 14.075 (3) Å

c = 13.856 (3) Å

β = 90.106 (3)°

V = 1786.1 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.58 mm−1

T = 188 K

0.20 × 0.03 × 0.03 mm

Data collection

Bruker P4/SMART 1000 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.626, T max = 0.938

12064 measured reflections

3967 independent reflections

2885 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.087

S = 1.16

3967 reflections

185 parameters

H-atom parameters constrained

Δρmax = 1.02 e Å−3

Δρmin = −0.72 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008b ▶); molecular graphics: DIAMOND (Brandenburg, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813028985/lh5663sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028985/lh5663Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028985/lh5663Isup3.cdx

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

[In2(CH3)4(C6H4O2)(C5H5N)]	F(000) = 928
Mr = 476.97	Dx = 1.774 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5671 reflections
a = 9.1584 (17) Å	θ = 2.7–27.9°
b = 14.075 (3) Å	µ = 2.58 mm−1
c = 13.856 (3) Å	T = 188 K
β = 90.106 (3)°	Rod, colourless
V = 1786.1 (6) Å3	0.20 × 0.03 × 0.03 mm
Z = 4

Bruker P4/SMART 1000 diffractometer	3967 independent reflections
Radiation source: fine-focus sealed tube, K760	2885 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −10→11
Tmin = 0.626, Tmax = 0.938	k = −18→18
12064 measured reflections	l = −16→17

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H-atom parameters constrained
S = 1.16	w = 1/[σ2(Fo2) + (0.0339P)2 + 1.2232P] where P = (Fo2 + 2Fc2)/3
3967 reflections	(Δ/σ)max = 0.001
185 parameters	Δρmax = 1.02 e Å−3
0 restraints	Δρmin = −0.72 e Å−3

Experimental. Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement._reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences.

	x	y	z	Uiso*/Ueq
In1	0.12136 (4)	0.57110 (3)	0.43640 (3)	0.03464 (12)
In2	0.11428 (4)	0.39665 (3)	1.01934 (3)	0.02955 (11)
O1	0.0623 (4)	0.5253 (3)	0.5809 (2)	0.0361 (8)
O2	0.0754 (3)	0.5316 (2)	0.9254 (2)	0.0300 (8)
N1	0.0635 (5)	0.2789 (3)	1.1488 (3)	0.0396 (11)
C1	0.0184 (8)	0.7054 (5)	0.4259 (6)	0.073 (2)
H1A	0.0580	0.7480	0.4755	0.109*
H1B	−0.0870	0.6980	0.4356	0.109*
H1C	0.0365	0.7325	0.3619	0.109*
C2	0.3108 (7)	0.4920 (5)	0.3979 (5)	0.0631 (19)
H2A	0.3153	0.4856	0.3276	0.095*
H2B	0.3060	0.4288	0.4275	0.095*
H2C	0.3981	0.5253	0.4211	0.095*
C3	0.0431 (7)	0.3018 (4)	0.9068 (4)	0.0562 (17)
H3A	0.1234	0.2910	0.8616	0.084*
H3B	−0.0397	0.3302	0.8724	0.084*
H3C	0.0130	0.2412	0.9353	0.084*
C4	0.3053 (6)	0.4553 (4)	1.0846 (4)	0.0454 (15)
H4A	0.3067	0.5242	1.0746	0.068*
H4B	0.3923	0.4269	1.0553	0.068*
H4C	0.3047	0.4417	1.1540	0.068*
C5	0.1383 (5)	0.5416 (3)	0.6650 (3)	0.0270 (10)
C6	0.0693 (5)	0.5259 (3)	0.7530 (3)	0.0277 (11)
H6	−0.0282	0.5029	0.7544	0.033*
C7	0.1435 (5)	0.5439 (3)	0.8395 (3)	0.0264 (10)
C8	0.2872 (5)	0.5754 (4)	0.8361 (4)	0.0314 (11)
H8	0.3395	0.5870	0.8941	0.038*
C9	0.3536 (6)	0.5897 (4)	0.7479 (4)	0.0371 (13)
H9	0.4518	0.6115	0.7462	0.044*
C10	0.2808 (5)	0.5731 (3)	0.6622 (3)	0.0311 (11)
H10	0.3282	0.5832	0.6022	0.037*
C11	−0.0627 (6)	0.2311 (4)	1.1471 (5)	0.0464 (14)
H11	−0.1250	0.2380	1.0927	0.056*
C12	−0.1062 (7)	0.1719 (4)	1.2216 (5)	0.0572 (17)
H12	−0.1960	0.1383	1.2176	0.069*
C13	−0.0192 (8)	0.1624 (5)	1.3002 (5)	0.066 (2)
H13	−0.0476	0.1223	1.3520	0.080*
C14	0.1099 (8)	0.2112 (5)	1.3044 (5)	0.0614 (18)
H14	0.1723	0.2061	1.3590	0.074*
C15	0.1467 (7)	0.2677 (4)	1.2274 (4)	0.0479 (15)
H15	0.2369	0.3010	1.2302	0.057*

	U11	U22	U33	U12	U13	U23
In1	0.0337 (2)	0.0504 (2)	0.0198 (2)	−0.00910 (16)	0.00038 (15)	0.00502 (16)
In2	0.0284 (2)	0.0370 (2)	0.02328 (19)	0.00222 (15)	0.00004 (14)	−0.00206 (15)
O1	0.035 (2)	0.058 (2)	0.0152 (17)	−0.0138 (17)	−0.0001 (15)	0.0008 (16)
O2	0.0281 (18)	0.047 (2)	0.0149 (17)	0.0054 (15)	0.0021 (14)	0.0016 (15)
N1	0.039 (3)	0.040 (3)	0.040 (3)	0.001 (2)	0.004 (2)	0.003 (2)
C1	0.080 (5)	0.058 (4)	0.081 (5)	−0.005 (4)	−0.005 (4)	0.018 (4)
C2	0.043 (4)	0.103 (6)	0.044 (4)	−0.001 (4)	0.004 (3)	−0.014 (4)
C3	0.078 (5)	0.054 (4)	0.037 (3)	−0.002 (3)	0.002 (3)	−0.018 (3)
C4	0.034 (3)	0.051 (4)	0.051 (4)	−0.007 (3)	−0.011 (3)	0.011 (3)
C5	0.035 (3)	0.032 (3)	0.014 (2)	−0.001 (2)	−0.001 (2)	0.0007 (19)
C6	0.022 (2)	0.040 (3)	0.022 (3)	−0.004 (2)	−0.001 (2)	0.000 (2)
C7	0.031 (3)	0.030 (3)	0.019 (2)	0.006 (2)	0.001 (2)	0.001 (2)
C8	0.028 (3)	0.048 (3)	0.018 (2)	−0.003 (2)	−0.004 (2)	−0.001 (2)
C9	0.025 (3)	0.058 (4)	0.029 (3)	−0.007 (2)	−0.001 (2)	0.004 (2)
C10	0.031 (3)	0.046 (3)	0.016 (2)	−0.007 (2)	0.003 (2)	−0.001 (2)
C11	0.049 (4)	0.040 (3)	0.050 (4)	−0.003 (3)	−0.002 (3)	0.001 (3)
C12	0.049 (4)	0.047 (4)	0.076 (5)	−0.010 (3)	0.009 (4)	0.009 (3)
C13	0.065 (5)	0.065 (5)	0.069 (5)	0.001 (4)	0.013 (4)	0.024 (4)
C14	0.073 (5)	0.069 (5)	0.042 (4)	0.011 (4)	−0.004 (3)	0.020 (3)
C15	0.050 (4)	0.048 (4)	0.046 (4)	0.001 (3)	0.002 (3)	0.008 (3)

In1—C1	2.118 (7)	C3—H3C	0.9800
In1—C2	2.130 (6)	C4—H4A	0.9800
In1—O1	2.172 (3)	C4—H4B	0.9800
In1—O1i	2.174 (3)	C4—H4C	0.9800
In2—C4	2.134 (5)	C5—C10	1.379 (7)
In2—O2ii	2.152 (3)	C5—C6	1.393 (6)
In2—C3	2.152 (5)	C6—C7	1.400 (6)
In2—O2	2.330 (3)	C6—H6	0.9500
In2—N1	2.486 (4)	C7—C8	1.390 (7)
O1—C5	1.376 (5)	C8—C9	1.380 (7)
O1—In1i	2.174 (3)	C8—H8	0.9500
O2—C7	1.355 (5)	C9—C10	1.381 (7)
O2—In2ii	2.152 (3)	C9—H9	0.9500
N1—C11	1.337 (7)	C10—H10	0.9500
N1—C15	1.338 (7)	C11—C12	1.385 (8)
C1—H1A	0.9800	C11—H11	0.9500
C1—H1B	0.9800	C12—C13	1.355 (9)
C1—H1C	0.9800	C12—H12	0.9500
C2—H2A	0.9800	C13—C14	1.368 (9)
C2—H2B	0.9800	C13—H13	0.9500
C2—H2C	0.9800	C14—C15	1.373 (8)
C3—H3A	0.9800	C14—H14	0.9500
C3—H3B	0.9800	C15—H15	0.9500
C1—In1—C2	144.3 (3)	H3A—C3—H3C	109.5
C1—In1—O1	102.5 (2)	H3B—C3—H3C	109.5
C2—In1—O1	106.3 (2)	In2—C4—H4A	109.5
C1—In1—O1i	101.9 (2)	In2—C4—H4B	109.5
C2—In1—O1i	106.1 (2)	H4A—C4—H4B	109.5
O1—In1—O1i	73.87 (14)	In2—C4—H4C	109.5
C4—In2—O2ii	109.25 (19)	H4A—C4—H4C	109.5
C4—In2—C3	142.5 (2)	H4B—C4—H4C	109.5
O2ii—In2—C3	107.8 (2)	O1—C5—C10	120.5 (4)
C4—In2—O2	92.62 (17)	O1—C5—C6	119.0 (4)
O2ii—In2—O2	72.15 (13)	C10—C5—C6	120.4 (4)
C3—In2—O2	93.2 (2)	C5—C6—C7	120.0 (4)
C4—In2—N1	96.11 (19)	C5—C6—H6	120.0
O2ii—In2—N1	84.49 (13)	C7—C6—H6	120.0
C3—In2—N1	93.0 (2)	O2—C7—C8	120.5 (4)
O2—In2—N1	156.63 (13)	O2—C7—C6	120.3 (4)
C5—O1—In1	127.2 (3)	C8—C7—C6	119.1 (4)
C5—O1—In1i	126.0 (3)	C9—C8—C7	119.8 (5)
In1—O1—In1i	106.13 (14)	C9—C8—H8	120.1
C7—O2—In2ii	128.7 (3)	C7—C8—H8	120.1
C7—O2—In2	121.6 (3)	C8—C9—C10	121.5 (5)
In2ii—O2—In2	107.85 (13)	C8—C9—H9	119.2
C11—N1—C15	116.4 (5)	C10—C9—H9	119.2
C11—N1—In2	119.1 (4)	C5—C10—C9	119.1 (4)
C15—N1—In2	124.0 (4)	C5—C10—H10	120.4
In1—C1—H1A	109.5	C9—C10—H10	120.4
In1—C1—H1B	109.5	N1—C11—C12	122.7 (6)
H1A—C1—H1B	109.5	N1—C11—H11	118.7
In1—C1—H1C	109.5	C12—C11—H11	118.7
H1A—C1—H1C	109.5	C13—C12—C11	119.2 (6)
H1B—C1—H1C	109.5	C13—C12—H12	120.4
In1—C2—H2A	109.5	C11—C12—H12	120.4
In1—C2—H2B	109.5	C12—C13—C14	119.5 (6)
H2A—C2—H2B	109.5	C12—C13—H13	120.3
In1—C2—H2C	109.5	C14—C13—H13	120.3
H2A—C2—H2C	109.5	C13—C14—C15	118.1 (7)
H2B—C2—H2C	109.5	C13—C14—H14	120.9
In2—C3—H3A	109.5	C15—C14—H14	120.9
In2—C3—H3B	109.5	N1—C15—C14	124.1 (6)
H3A—C3—H3B	109.5	N1—C15—H15	118.0
In2—C3—H3C	109.5	C14—C15—H15	118.0