Trichlorido(4,4′-dimethyl-2,2′-bipyridine-κ2N,N′)(dimethyl sulfoxide-κO)indium(III)

Ahmadi, R.; Kalateh, K.; Abedi, A.; Amani, V.; Khavasi, H.R.

doi:10.1107/S1600536808029553

Trichlorido(4,4′-dimethyl-2,2′-bipyridine-κ²N,N′)(dimethyl sulfoxide-κO)indium(III)

R. Ahmadi, K. Kalateh, A. Abedi, V. Amani and H. R. Khavasi

In the molecule of the title compound, [InCl₃(C₁₂H₁₂N₂)(C₂H₆OS)], the In^III atom is six-coordinated in a distorted octahedral configuration by two N atoms from the chelating 4,4′-dimethyl-2,2′-bipyridine ligand, one O atom from dimethyl sulfoxide and three Cl atoms. In the crystal structure, intermolecular C—H

Cl hydrogen bonds link the molecules into centrosymmetric dimers.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808029553/hk2532sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808029553/hk2532Isup2.hkl Contains datablock I

CCDC reference: 705978

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Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R factor = 0.036
wR factor = 0.086
Data-to-parameter ratio = 25.1

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Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C4
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C10

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
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   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
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Comment top

Recently, we reported the syntheses and crystal structures of [Zn(5,5'-dmbpy)Cl₂], (II), (Khalighi et al., 2008), [Zn(6-mbpy)Cl₂], (III), (Ahmadi, Kalateh et al., 2008), [Cd(5,5'-dmbpy)(µ-Cl)₂]_n, (IV), (Ahmadi, Khalighi et al., 2008), (Hg(4,4'-dmbpy)I₂], (V), (Yousefi, Tadayon Pour et al., 2008) and [Cu(5,5'-dcbpy)(en)(H₂O)₂].2.5H₂O, (VI), (Yousefi, Khalighi et al., 2008) [where 5,5'-dmbpy is 5,5'-dimethyl-2,2'-bipyridine, 6-mbpy is 6-methyl-2,2'-bipyridine, 4,4'-dmbpy is 4,4'-dimethyl-2,2'-bipyridine, 5,5'-dcbpy is 2,2'-bipyridine-5,5'-dicarboxylate and en is ethylenediamine]. We have also reported the synthesis and crystal structures of iron(III) complexes of [Fe(bipy)Cl₃(DMSO)], (VII) and [Fe(phen)Cl₃(DMSO)], (VIII), (Amani et al., 2007) and [Fe(phen)Cl₃(CH₃OH)].CH₃OH, (IX), (Khavasi et al., 2007) [where bipy is 2,2'-bipyridine, DMSO is dimethyl sulfoxide and phen is 1,10-phenanthroline]. There are several In^III complexes, with formula, [In(N—N)Cl₃(L)], (L = DMSO, H₂O and EtOH), such as [In(bipy)Cl₃(H₂O)], (X), [In(bipy)Cl₃(EtOH)], (XI) and [In(bipy)Cl₃(H₂O)].H₂O, (XII), (Malyarick et al., 1992), [In(phen)Cl₃(DMSO)], (XIII), (Nan et al., 1987), [In(phen)Cl₃(H₂O)], (XIV) and [In(phen)Cl₃(EtOH)].EtOH, (XV), (Ilyukhin & Malyarick, 1994) have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound, (I).

In the title compound, (Fig. 1), the In^III atom is six-coordinated in a distorted octahedral configuration by two N atoms from 4,4'-dimethyl-2,2' -bipyridine, one O atom from dimethyl sulfoxide and three Cl atoms. The In—Cl and In—N bond lengths and angles (Table 1) are within normal ranges, as in (XI), (XII), (XIII) and (XV).

In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 2) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For related literature, see: Ahmadi, Kalateh et al. (2008); Ahmadi, Khalighi et al. (2008); Amani et al. (2007); Ilyukhin & Malyarick (1994); Khavasi et al. (2007); Khalighi et al. (2008); Malyarick et al. (1992); Nan et al. (1987); Yousefi, Khalighi et al. (2008); Yousefi, Tadayon Pour et al. (2008).

Experimental top

For the preparation of the title compound, (I), a solution of 4,4'-dimethyl -2,2'-bipyridine (0.20 g, 1.10 mmol) in methanol (10 ml) was added to a solution of InCl₃.4H₂O (0.16 g, 0.55 mmol) in methanol (5 ml) at room temperature. The suitable crystals for X-ray analysis were isolated after one week by methanol diffusion to a colorless solution in DMSO (yield; 0.19 g, 71.4%).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Trichlorido(4,4'-dimethyl-2,2'-bipyridine-κ²N,N')(dimethyl sulfoxide-κO)indium(III) top

Crystal data top

[InCl₃(C₁₂H₁₂N₂)(C₂H₆OS)]	F(000) = 960
M_r = 483.54	D_x = 1.704 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2052 reflections
a = 8.2565 (17) Å	θ = 1.7–29.3°
b = 23.456 (5) Å	µ = 1.79 mm⁻¹
c = 10.121 (2) Å	T = 298 K
β = 105.95 (3)°	Prism, colorless
V = 1884.7 (7) Å³	0.49 × 0.46 × 0.44 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	5046 independent reflections
Radiation source: fine-focus sealed tube	4804 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 29.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −11→11
T_min = 0.404, T_max = 0.455	k = −28→32
13791 measured reflections	l = −13→12

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.0263P)² + 2.6542P] where P = (F_o² + 2F_c²)/3
5046 reflections	(Δ/σ)_max = 0.018
201 parameters	Δρ_max = 0.86 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[InCl₃(C₁₂H₁₂N₂)(C₂H₆OS)]	V = 1884.7 (7) Å³
M_r = 483.54	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.2565 (17) Å	µ = 1.79 mm⁻¹
b = 23.456 (5) Å	T = 298 K
c = 10.121 (2) Å	0.49 × 0.46 × 0.44 mm
β = 105.95 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5046 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	4804 reflections with I > 2σ(I)
T_min = 0.404, T_max = 0.455	R_int = 0.038
13791 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.16	Δρ_max = 0.86 e Å⁻³
5046 reflections	Δρ_min = −0.69 e Å⁻³
201 parameters

Special details top

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. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
In1	0.67799 (2)	0.143868 (8)	0.722848 (19)	0.03114 (7)
Cl1	0.46060 (14)	0.15508 (4)	0.50881 (9)	0.0586 (2)
Cl2	0.89844 (14)	0.10102 (4)	0.63344 (12)	0.0620 (3)
Cl3	0.78999 (10)	0.24070 (3)	0.74202 (8)	0.04094 (16)
S1	0.41807 (11)	0.23105 (4)	0.82159 (9)	0.04457 (18)
O1	0.4998 (3)	0.17216 (10)	0.8405 (2)	0.0410 (5)
N1	0.5893 (3)	0.05448 (10)	0.7626 (2)	0.0345 (5)
N2	0.8245 (3)	0.11591 (10)	0.9400 (2)	0.0329 (5)
C1	0.4701 (4)	0.02601 (15)	0.6694 (3)	0.0443 (7)
H1	0.4125	0.0447	0.5892	0.053*
C2	0.4290 (4)	−0.03006 (14)	0.6877 (3)	0.0440 (7)
H2	0.3452	−0.0484	0.6207	0.053*
C3	0.5131 (4)	−0.05872 (13)	0.8059 (3)	0.0378 (6)
C4	0.4753 (5)	−0.12005 (14)	0.8289 (4)	0.0501 (8)
H4A	0.4398	−0.1232	0.9113	0.060*
H4B	0.5747	−0.1426	0.8378	0.060*
H4C	0.3872	−0.1335	0.7522	0.060*
C5	0.6370 (4)	−0.02882 (13)	0.9026 (3)	0.0369 (6)
H5	0.6968	−0.0468	0.9832	0.044*
C6	0.6714 (3)	0.02770 (12)	0.8790 (3)	0.0308 (5)
C7	0.8006 (3)	0.06232 (12)	0.9795 (3)	0.0311 (5)
C8	0.8859 (4)	0.04184 (13)	1.1078 (3)	0.0359 (6)
H8	0.8674	0.0047	1.1325	0.043*
C9	1.0000 (4)	0.07688 (13)	1.2006 (3)	0.0374 (6)
C10	1.0914 (5)	0.05639 (17)	1.3414 (4)	0.0530 (9)
H10A	1.0620	0.0799	1.4089	0.064*
H10B	1.2106	0.0585	1.3532	0.064*
H10C	1.0601	0.0176	1.3524	0.064*
C11	1.0221 (4)	0.13209 (14)	1.1568 (3)	0.0403 (6)
H11	1.0970	0.1569	1.2147	0.048*
C12	0.9325 (4)	0.14978 (13)	1.0270 (3)	0.0400 (6)
H12	0.9482	0.1867	0.9995	0.048*
C13	0.5259 (7)	0.2699 (2)	0.9695 (5)	0.0731 (13)
H13A	0.6407	0.2757	0.9686	0.088*
H13B	0.5234	0.2489	1.0504	0.088*
H13C	0.4720	0.3061	0.9699	0.088*
C14	0.2249 (5)	0.2199 (2)	0.8626 (5)	0.0722 (13)
H14A	0.2464	0.2014	0.9503	0.087*
H14B	0.1527	0.1963	0.7935	0.087*
H14C	0.1711	0.2559	0.8661	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
In1	0.03794 (11)	0.02645 (10)	0.03083 (10)	−0.00110 (7)	0.01249 (7)	0.00088 (7)
Cl1	0.0729 (6)	0.0538 (5)	0.0380 (4)	−0.0016 (4)	−0.0033 (4)	0.0062 (3)
Cl2	0.0772 (6)	0.0409 (4)	0.0877 (7)	0.0027 (4)	0.0561 (6)	−0.0066 (4)
Cl3	0.0448 (4)	0.0282 (3)	0.0536 (4)	−0.0030 (3)	0.0197 (3)	0.0006 (3)
S1	0.0475 (4)	0.0469 (4)	0.0438 (4)	0.0125 (3)	0.0200 (3)	0.0068 (3)
O1	0.0441 (11)	0.0412 (12)	0.0434 (11)	0.0053 (9)	0.0216 (9)	0.0042 (9)
N1	0.0379 (12)	0.0297 (12)	0.0350 (11)	−0.0049 (9)	0.0085 (9)	−0.0006 (9)
N2	0.0326 (11)	0.0296 (11)	0.0373 (12)	−0.0019 (9)	0.0111 (9)	0.0009 (9)
C1	0.0473 (17)	0.0394 (16)	0.0392 (15)	−0.0067 (14)	0.0002 (13)	0.0022 (12)
C2	0.0460 (17)	0.0384 (16)	0.0441 (16)	−0.0122 (13)	0.0067 (13)	−0.0062 (13)
C3	0.0455 (15)	0.0313 (14)	0.0406 (14)	−0.0055 (12)	0.0183 (12)	−0.0046 (11)
C4	0.068 (2)	0.0322 (16)	0.0527 (19)	−0.0109 (15)	0.0213 (17)	−0.0040 (14)
C5	0.0446 (15)	0.0312 (14)	0.0354 (13)	−0.0030 (12)	0.0116 (12)	0.0015 (11)
C6	0.0335 (12)	0.0290 (13)	0.0311 (12)	−0.0019 (10)	0.0109 (10)	−0.0028 (10)
C7	0.0329 (12)	0.0294 (13)	0.0321 (12)	0.0000 (10)	0.0109 (10)	−0.0018 (10)
C8	0.0405 (14)	0.0284 (13)	0.0382 (14)	−0.0002 (11)	0.0095 (11)	−0.0007 (11)
C9	0.0377 (14)	0.0364 (15)	0.0356 (14)	0.0029 (12)	0.0059 (11)	−0.0030 (11)
C10	0.061 (2)	0.051 (2)	0.0391 (16)	0.0022 (17)	−0.0007 (15)	0.0011 (14)
C11	0.0388 (15)	0.0365 (15)	0.0424 (15)	−0.0051 (12)	0.0058 (12)	−0.0067 (12)
C12	0.0416 (15)	0.0314 (14)	0.0478 (16)	−0.0073 (12)	0.0136 (13)	−0.0020 (12)
C13	0.091 (3)	0.064 (3)	0.079 (3)	−0.017 (2)	0.048 (3)	−0.028 (2)
C14	0.042 (2)	0.100 (4)	0.079 (3)	0.017 (2)	0.025 (2)	0.007 (3)

Geometric parameters (Å, º) top

Cl1—In1	2.4180 (12)	C7—N2	1.350 (4)
Cl2—In1	2.4592 (10)	C7—C8	1.382 (4)
Cl3—In1	2.4398 (9)	C8—C9	1.400 (4)
O1—In1	2.233 (2)	C8—H8	0.9300
O1—S1	1.526 (2)	C9—C11	1.397 (4)
N1—In1	2.293 (2)	C9—C10	1.497 (4)
N2—In1	2.294 (2)	C10—H10A	0.9600
C1—N1	1.339 (4)	C10—H10B	0.9600
C1—C2	1.383 (5)	C10—H10C	0.9600
C1—H1	0.9300	C11—C12	1.382 (5)
C2—C3	1.382 (5)	C11—H11	0.9300
C2—H2	0.9300	C12—N2	1.331 (4)
C3—C5	1.395 (4)	C12—H12	0.9300
C3—C4	1.504 (4)	C13—S1	1.770 (5)
C4—H4A	0.9600	C13—H13A	0.9600
C4—H4B	0.9600	C13—H13B	0.9600
C4—H4C	0.9600	C13—H13C	0.9600
C5—C6	1.390 (4)	C14—S1	1.775 (4)
C5—H5	0.9300	C14—H14A	0.9600
C6—N1	1.343 (4)	C14—H14B	0.9600
C6—C7	1.495 (4)	C14—H14C	0.9600

Cl1—In1—Cl2	99.03 (4)	H4B—C4—H4C	109.5
Cl1—In1—Cl3	98.15 (3)	C6—C5—C3	120.3 (3)
Cl3—In1—Cl2	96.15 (3)	C6—C5—H5	119.9
O1—In1—Cl1	90.56 (7)	C3—C5—H5	119.9
O1—In1—Cl2	168.67 (6)	N1—C6—C5	121.3 (3)
O1—In1—Cl3	88.39 (6)	N1—C6—C7	115.9 (2)
O1—In1—N1	83.64 (9)	C5—C6—C7	122.8 (3)
O1—In1—N2	79.94 (9)	N2—C7—C8	121.6 (3)
N1—In1—Cl1	93.59 (7)	N2—C7—C6	116.1 (2)
N1—In1—Cl2	89.72 (7)	C8—C7—C6	122.3 (3)
N1—In1—Cl3	165.87 (6)	C7—C8—C9	120.1 (3)
N2—In1—Cl1	162.86 (7)	C7—C8—H8	119.9
N2—In1—Cl2	89.26 (7)	C9—C8—H8	119.9
N2—In1—Cl3	95.83 (7)	C11—C9—C8	117.0 (3)
N1—In1—N2	71.34 (9)	C11—C9—C10	121.6 (3)
O1—S1—C13	104.9 (2)	C8—C9—C10	121.4 (3)
O1—S1—C14	103.4 (2)	C9—C10—H10A	109.5
C13—S1—C14	98.8 (2)	C9—C10—H10B	109.5
H14B—C14—H14C	109.5	H10A—C10—H10B	109.5
S1—O1—In1	122.38 (12)	C9—C10—H10C	109.5
C1—N1—C6	118.7 (3)	H10A—C10—H10C	109.5
C1—N1—In1	122.7 (2)	H10B—C10—H10C	109.5
C6—N1—In1	118.26 (18)	C12—C11—C9	119.8 (3)
C12—N2—C7	119.1 (3)	C12—C11—H11	120.1
C12—N2—In1	123.0 (2)	C9—C11—H11	120.1
C7—N2—In1	117.94 (18)	N2—C12—C11	122.4 (3)
N1—C1—C2	122.7 (3)	N2—C12—H12	118.8
N1—C1—H1	118.7	C11—C12—H12	118.8
C2—C1—H1	118.7	S1—C13—H13A	109.5
C3—C2—C1	119.7 (3)	S1—C13—H13B	109.5
C3—C2—H2	120.2	H13A—C13—H13B	109.5
C1—C2—H2	120.2	S1—C13—H13C	109.5
C2—C3—C5	117.4 (3)	H13A—C13—H13C	109.5
C2—C3—C4	121.6 (3)	H13B—C13—H13C	109.5
C5—C3—C4	121.1 (3)	S1—C14—H14A	109.5
C3—C4—H4A	109.5	S1—C14—H14B	109.5
C3—C4—H4B	109.5	H14A—C14—H14B	109.5
H4A—C4—H4B	109.5	S1—C14—H14C	109.5
C3—C4—H4C	109.5	H14A—C14—H14C	109.5
H4A—C4—H4C	109.5

S1—O1—In1—N1	−154.51 (17)	N1—C1—C2—C3	−0.1 (5)
S1—O1—In1—N2	133.38 (17)	C1—C2—C3—C5	0.2 (5)
S1—O1—In1—Cl1	−60.97 (15)	C1—C2—C3—C4	−178.7 (3)
S1—O1—In1—Cl3	37.17 (15)	C2—C3—C5—C6	0.4 (5)
S1—O1—In1—Cl2	151.0 (2)	C4—C3—C5—C6	179.4 (3)
C1—N1—In1—O1	98.2 (3)	C3—C5—C6—N1	−1.2 (4)
C6—N1—In1—O1	−88.1 (2)	C3—C5—C6—C7	179.0 (3)
C1—N1—In1—N2	179.7 (3)	C5—C6—N1—C1	1.3 (4)
C6—N1—In1—N2	−6.6 (2)	C7—C6—N1—C1	−178.9 (3)
C1—N1—In1—Cl1	8.0 (3)	C5—C6—N1—In1	−172.7 (2)
C6—N1—In1—Cl1	−178.3 (2)	C7—C6—N1—In1	7.1 (3)
C1—N1—In1—Cl3	154.2 (2)	N1—C6—C7—N2	−2.2 (4)
C6—N1—In1—Cl3	−32.1 (4)	C5—C6—C7—N2	177.6 (3)
C1—N1—In1—Cl2	−91.0 (3)	N1—C6—C7—C8	175.1 (3)
C6—N1—In1—Cl2	82.7 (2)	C5—C6—C7—C8	−5.1 (4)
C12—N2—In1—O1	−88.9 (2)	C8—C7—N2—C12	−0.2 (4)
C7—N2—In1—O1	91.9 (2)	C6—C7—N2—C12	177.1 (3)
C12—N2—In1—N1	−175.5 (3)	C8—C7—N2—In1	179.0 (2)
C7—N2—In1—N1	5.30 (19)	C6—C7—N2—In1	−3.7 (3)
C12—N2—In1—Cl1	−146.1 (2)	N2—C7—C8—C9	0.2 (4)
C7—N2—In1—Cl1	34.7 (4)	C6—C7—C8—C9	−177.0 (3)
C12—N2—In1—Cl3	−1.6 (2)	C7—C8—C9—C11	−0.2 (4)
C7—N2—In1—Cl3	179.24 (19)	C7—C8—C9—C10	178.6 (3)
C12—N2—In1—Cl2	94.5 (2)	C8—C9—C11—C12	0.3 (5)
C7—N2—In1—Cl2	−84.65 (19)	C10—C9—C11—C12	−178.5 (3)
In1—O1—S1—C13	−105.2 (2)	C9—C11—C12—N2	−0.3 (5)
In1—O1—S1—C14	151.6 (2)	C11—C12—N2—C7	0.3 (5)
C2—C1—N1—C6	−0.6 (5)	C11—C12—N2—In1	−178.9 (2)
C2—C1—N1—In1	173.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1	0.93	2.77	3.427 (4)	128
C10—H10C···Cl2ⁱ	0.96	2.80	3.700 (4)	156

Symmetry code: (i) −x+2, −y, −z+2.

Experimental details

Crystal data
Chemical formula	[InCl₃(C₁₂H₁₂N₂)(C₂H₆OS)]
M_r	483.54
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.2565 (17), 23.456 (5), 10.121 (2)
β (°)	105.95 (3)
V (Å³)	1884.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.79
Crystal size (mm)	0.49 × 0.46 × 0.44

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.404, 0.455
No. of measured, independent and observed [I > 2σ(I)] reflections	13791, 5046, 4804
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.689

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.085, 1.16
No. of reflections	5046
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.69

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Cl1—In1	2.4180 (12)	O1—In1	2.233 (2)
Cl2—In1	2.4592 (10)	N1—In1	2.293 (2)
Cl3—In1	2.4398 (9)	N2—In1	2.294 (2)

Cl1—In1—Cl2	99.03 (4)	N1—In1—Cl1	93.59 (7)
Cl1—In1—Cl3	98.15 (3)	N1—In1—Cl2	89.72 (7)
Cl3—In1—Cl2	96.15 (3)	N1—In1—Cl3	165.87 (6)
O1—In1—Cl1	90.56 (7)	N2—In1—Cl1	162.86 (7)
O1—In1—Cl2	168.67 (6)	N2—In1—Cl2	89.26 (7)
O1—In1—Cl3	88.39 (6)	N2—In1—Cl3	95.83 (7)
O1—In1—N1	83.64 (9)	N1—In1—N2	71.34 (9)
O1—In1—N2	79.94 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1	0.93	2.77	3.427 (4)	128.00
C10—H10C···Cl2ⁱ	0.96	2.80	3.700 (4)	156.00

Symmetry code: (i) −x+2, −y, −z+2.

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