Bis­(μ-pyridine-2,3-dicarboxyl­ato)bis­[aqua­(3-carb­oxy­pyridine-2-carboxyl­ato)indium(III)] tetra­hydrate

In the binuclear centrosymmetric title compound, [In₂(C₇H₃NO₄)₂(C₇H₄NO₄)₂(H₂O)₂]·4H₂O, which contains both pyridine-2,3-dicarboxyl­ate and 3-carb­oxy­pyridine-2-carboxyl­ate ligands, the In^III atom is six-coordinated in a distorted octa­hedral geometry. One pyridine ligand is N,O-chelated while the other is N,O-chelated and at the same time bridging to the other via the second carboxyl group. In the crystal, an extensive O—H...O hydrogen-bonding network, involving the coordinated and lattice water mol­ecules and the carboxyl groups of the ligands, together with C—H...O and π–π inter­actions [centroid–centroid distance = 3.793 (1) Å], leads to the formation of a three-dimensional structure.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.016
• wR factor = 0.039
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11    ..  O3      ..       2.61 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          6
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         13
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600        345

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT432_ALERT_2_G Short Inter X...Y Contact  O2     ..  C12     ..       2.99 Ang.

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

For several years our research group, among others, has been interested in the synthesis of new coordination compounds from polycarboxylic acids and amines using a proton transfer methodology (Aghabozorg, Daneshvar, et al., 2007; Aghabozorg, Khadivi, et al., 2008; Aghabozorg, Ramezanipour, et al., 2006; Eshtiagh-Hosseini et al., 2010; Mirzaei et al., 2011). Polycarboxylate ligands are versatile because of their diversity of coordination modes and also because of their ability to initiate self assembly processes by supramolecular interactions (Kondo et al., 1999; Beobide et al., 2006). In the majority of the complexes obtained by proton-transfer methods the metal complex is anionic with the cation derived from the amine used in the synthesis. Among these multicarboxylate ligands, pyridine-2,3-dicarboxylic acid (py-2,3dcH₂) has rarely been used under the conditions generally employed in our studies. In the course of this work we prepared the title binuclear indium(II) compound, whose crystal structure we report on herein.

In addition to being a neutral complex, the title compound (Fig. 1) appears to be the first indium^III complex N,O chelated by one py-2,3-dcH^- ion and one py-2,3-dc^2-ion, with the latter using the carboxyl group in the 3-position to bridge to a second metal. In the resulting centrosymmetric dimer, the coordination sphere of each metal is completed by a water molecule. The O₄N₂ coordination sphere adopts a distorted octahedral geometry with the largest departure being the 75.30 (5)° angles subtended by the chelating ligands (Fig. 1). The average In—O distance of 2.1253 (14) Å is slightly shorter than the average In—N of 2.2478 (17) Å. This can be explained by Pearson's hard and soft acid-base concept (Schlemper et al., 1967).

The solid state structure can be described as chains of dimers associated via hydrogen bonding interactions between the coordinated water molecule, the monoprotonated carboxyl group and oxygen atoms in the pyridine dicarboxylate ligand as well as C—H···O interactons between ring hydrogen atoms and carboxylate oxygen atoms (Table 1). Additionally there is a slipped π-π stacking interaction (Fig. 2) between the (N1,C1-C5) ring and its counterpart in the dimer at -x+1, -y+2, -z+1 [perpendicular separation = 3.107 (1) Å, centroid-to-centroid distance = 3.793 (1) Å, slippage = 1.37 Å, angle between planes = 11.28 (8)° (Janiak, 2000)]. The chains are associated via hydrogen bonding interactions between the lattice water molecules, the coordinated water molecule and oxygen atoms of the carboxylate ligands (Table 1, Fig. 3) to complete the three-dimensional network structure (Krygowski et al., 1998).

A final interaction of significance is a complementary π-π stacking interaction (Fig. 2) between the C13═O6 moiety in one half of the dimer and the (N2,C8-C12) ring in the other half (centroid-to-centroid distance = 3.347 (2) Å, angle of the line joining the centroids to the plane of the ring = 74.7 (1)°).

Related literature

For metal complexes with polycarboxylate ligands, see: Aghabozorg, Daneshvar et al. (2007); Aghabozorg, Khadivi et al. (2008); Aghabozorg, Ramezanipour et al. (2006); Eshtiagh-Hosseini et al. (2010); Mirzaei et al. (2011). For examples of self-assembly, see: Kondo et al. (1999); Beobide et al. (2006). For a discussion of hard–soft acid base concepts, see: Schlemper et al. (1967). For examples of π–π stacking, see: Janiak (2000). For three-dimensional network structures, see: Krygowski et al. (1998).

S2. Experimental

A solution of In₂(SO₄)₃.xH₂O (34 mg, 0.06 mmol) in water (5 ml) was added dropwise to an aqueous solution of pyridine-2,3-dicarboxylic acid (10 mg, 0.06 mmol) and 2-amino-6-methyl pyridine (13 mg, 0.12 mmol) in a 1:1:2 molar ratio at reflux. The solution was cooled to room temperature and upon slow evaporation, X-ray quality crystals were formed which were collected and washed with distilled water.

S3. Refinement

The OH and water H-atoms were located in difference Fourier maps and were refined as riding atoms with U_iso(H) = 1.2U_eq(O). The C-bound H-atoms were placed in calculated positions and treated as riding atoms: C—H = 0.95 Å with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. View of the local coordination environments of In^III atoms in the title molecule, with 50% probability thermal ellipsoids. Primed atoms are related to the non-primed atoms by the center of symmetry.
	Fig. 2. Perspective view of the π···π and C—O···π stacking interactions (dashed lines) in the title compound (In = large green circles, H = small green circles, O = red circles, N = blue circles).
	Fig. 3. Perspective view of the crystal packing of the title compound, showing the intermolecular hydrogen bonds as dashed lines (In = large green circles, H = small green circles, O = red circles, N = blue circles; see Table 1 for details).

bis(µ-pyridine-2,3-dicarboxylato)bis[aqua(3-carboxypyridine-2- carboxylato)indium(III)] tetrahydrate

Crystal data

[In2(C7H3NO4)2(C7H4NO4)2(H2O)2]·4H2O	Z = 1
Mr = 1000.17	F(000) = 496
Triclinic, P1	Dx = 1.993 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0166 (3) Å	Cell parameters from 8569 reflections
b = 10.0890 (4) Å	θ = 2.8–27.2°
c = 11.9838 (5) Å	µ = 1.49 mm^−1
α = 110.069 (4)°	T = 120 K
β = 96.236 (3)°	Block, colourless
γ = 109.076 (3)°	0.40 × 0.30 × 0.30 mm
V = 833.36 (6) Å^3

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 detector	3373 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3168 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
Detector resolution: 8.4353 pixels mm^-1	θmax = 27.2°, θmin = 3.3°
ω scan	h = −8→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −12→12
Tmin = 0.588, Tmax = 0.664	l = −15→15
10774 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.016	H-atom parameters constrained
wR(F^2) = 0.039	w = 1/[σ^2(Fo^2) + (0.0197P)^2 + 0.3217P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.002
3373 reflections	Δρmax = 0.38 e Å^−3
254 parameters	Δρmin = −0.31 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0083 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
In1	0.716069 (17)	0.792788 (13)	0.730349 (10)	0.00941 (5)
O1	0.81082 (17)	0.78122 (15)	0.57022 (11)	0.0132 (3)
O2	0.77166 (18)	0.81433 (15)	0.39645 (11)	0.0165 (3)
O3	0.43118 (19)	0.60530 (14)	0.22385 (11)	0.0154 (3)
O4	0.38691 (19)	0.80920 (15)	0.21595 (11)	0.0179 (3)
H4O	0.3870	0.7721	0.1416	0.021*
O5	0.64775 (17)	0.86624 (14)	0.90207 (10)	0.0127 (3)
O6	0.73152 (19)	1.05169 (15)	1.08983 (11)	0.0171 (3)
O7	0.92356 (19)	1.40964 (15)	1.17662 (11)	0.0165 (3)
O8	1.10615 (18)	1.31541 (14)	1.24362 (11)	0.0144 (3)
O9	0.50749 (18)	0.56958 (14)	0.66940 (11)	0.0168 (3)
H91	0.3972	0.5539	0.6473	0.020*
H92	0.5325	0.5180	0.7057	0.020*
N1	0.5111 (2)	0.83155 (16)	0.61329 (13)	0.0105 (3)
N2	0.9159 (2)	1.03454 (17)	0.83361 (13)	0.0104 (3)
C1	0.5347 (2)	0.80161 (19)	0.49914 (15)	0.0101 (4)
C2	0.4018 (3)	0.78340 (19)	0.40403 (16)	0.0120 (4)
C3	0.2455 (3)	0.8044 (2)	0.43128 (17)	0.0159 (4)
H3	0.1527	0.7938	0.3685	0.019*
C4	0.2254 (3)	0.8406 (2)	0.54992 (17)	0.0165 (4)
H4	0.1209	0.8583	0.5699	0.020*
C5	0.3595 (3)	0.8508 (2)	0.63908 (16)	0.0135 (4)
H5	0.3442	0.8717	0.7200	0.016*
C6	0.7195 (2)	0.79807 (19)	0.48430 (15)	0.0107 (4)
C7	0.4120 (3)	0.7255 (2)	0.27281 (16)	0.0124 (4)
C8	0.9017 (3)	1.0999 (2)	0.94915 (15)	0.0100 (3)
C9	1.0201 (3)	1.2475 (2)	1.02728 (15)	0.0113 (4)
C10	1.1540 (3)	1.3289 (2)	0.98329 (16)	0.0153 (4)
H10	1.2361	1.4305	1.0348	0.018*
C11	1.1667 (3)	1.2612 (2)	0.86462 (16)	0.0158 (4)
H11	1.2570	1.3154	0.8335	0.019*
C12	1.0452 (3)	1.1130 (2)	0.79220 (16)	0.0131 (4)
H12	1.0537	1.0655	0.7107	0.016*
C13	0.7493 (3)	1.0014 (2)	0.98602 (15)	0.0113 (4)
C14	1.0119 (3)	1.3270 (2)	1.15813 (15)	0.0121 (4)
O10	0.39345 (18)	0.69562 (15)	−0.00496 (11)	0.0167 (3)
H101	0.4704	0.7512	−0.0293	0.020*
H102	0.2944	0.6616	−0.0572	0.020*
O11	0.83456 (19)	0.48403 (16)	0.39983 (12)	0.0217 (3)
H111	0.8943	0.5668	0.4609	0.026*
H112	0.8849	0.4755	0.3413	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
In1	0.00961 (8)	0.01133 (8)	0.00717 (7)	0.00362 (6)	0.00213 (5)	0.00400 (5)
O1	0.0104 (7)	0.0217 (7)	0.0097 (6)	0.0077 (6)	0.0033 (5)	0.0072 (5)
O2	0.0164 (8)	0.0241 (7)	0.0127 (6)	0.0077 (6)	0.0072 (6)	0.0105 (6)
O3	0.0209 (8)	0.0118 (6)	0.0123 (6)	0.0055 (6)	0.0014 (6)	0.0050 (5)
O4	0.0275 (9)	0.0184 (7)	0.0112 (6)	0.0112 (6)	0.0027 (6)	0.0084 (5)
O5	0.0112 (7)	0.0143 (6)	0.0108 (6)	0.0026 (6)	0.0040 (5)	0.0049 (5)
O6	0.0181 (8)	0.0196 (7)	0.0113 (6)	0.0046 (6)	0.0074 (6)	0.0049 (5)
O7	0.0191 (8)	0.0186 (7)	0.0129 (6)	0.0119 (6)	0.0014 (6)	0.0039 (5)
O8	0.0164 (8)	0.0191 (7)	0.0098 (6)	0.0102 (6)	0.0018 (5)	0.0055 (5)
O9	0.0132 (7)	0.0150 (7)	0.0218 (7)	0.0033 (6)	−0.0003 (6)	0.0106 (6)
N1	0.0104 (8)	0.0097 (7)	0.0111 (7)	0.0032 (6)	0.0033 (6)	0.0046 (6)
N2	0.0103 (8)	0.0124 (7)	0.0098 (7)	0.0047 (7)	0.0026 (6)	0.0054 (6)
C1	0.0104 (10)	0.0068 (8)	0.0122 (8)	0.0017 (7)	0.0028 (7)	0.0044 (7)
C2	0.0130 (10)	0.0083 (8)	0.0135 (8)	0.0021 (8)	0.0013 (7)	0.0056 (7)
C3	0.0128 (10)	0.0173 (9)	0.0183 (9)	0.0062 (8)	0.0001 (8)	0.0087 (8)
C4	0.0124 (10)	0.0161 (9)	0.0238 (10)	0.0074 (8)	0.0067 (8)	0.0089 (8)
C5	0.0145 (10)	0.0109 (9)	0.0158 (9)	0.0048 (8)	0.0068 (8)	0.0057 (7)
C6	0.0100 (10)	0.0088 (8)	0.0100 (8)	0.0015 (7)	0.0013 (7)	0.0023 (7)
C7	0.0072 (9)	0.0135 (9)	0.0136 (8)	0.0008 (8)	−0.0013 (7)	0.0063 (7)
C8	0.0104 (10)	0.0131 (9)	0.0094 (8)	0.0063 (8)	0.0027 (7)	0.0062 (7)
C9	0.0115 (10)	0.0142 (9)	0.0100 (8)	0.0068 (8)	0.0012 (7)	0.0058 (7)
C10	0.0149 (11)	0.0139 (9)	0.0139 (8)	0.0027 (8)	0.0007 (8)	0.0054 (7)
C11	0.0147 (11)	0.0171 (9)	0.0153 (9)	0.0027 (8)	0.0056 (8)	0.0090 (8)
C12	0.0142 (10)	0.0158 (9)	0.0107 (8)	0.0057 (8)	0.0050 (7)	0.0065 (7)
C13	0.0104 (10)	0.0148 (9)	0.0113 (8)	0.0070 (8)	0.0017 (7)	0.0067 (7)
C14	0.0103 (10)	0.0110 (9)	0.0115 (8)	0.0009 (8)	0.0015 (7)	0.0038 (7)
O10	0.0133 (7)	0.0224 (7)	0.0134 (6)	0.0027 (6)	0.0014 (5)	0.0106 (6)
O11	0.0204 (8)	0.0215 (7)	0.0203 (7)	0.0069 (6)	0.0059 (6)	0.0061 (6)

Geometric parameters (Å, º)

In1—O8^i	2.1153 (12)	C1—C2	1.390 (2)
In1—O1	2.1199 (12)	C1—C6	1.522 (2)
In1—O9	2.1319 (13)	C2—C3	1.392 (3)
In1—O5	2.1324 (11)	C2—C7	1.500 (2)
In1—N2	2.2339 (15)	C3—C4	1.383 (3)
In1—N1	2.2618 (14)	C3—H3	0.9500
O1—C6	1.289 (2)	C4—C5	1.383 (3)
O2—C6	1.216 (2)	C4—H4	0.9500
O3—C7	1.221 (2)	C5—H5	0.9500
O4—C7	1.302 (2)	C8—C9	1.386 (3)
O4—H4O	0.8401	C8—C13	1.517 (3)
O5—C13	1.300 (2)	C9—C10	1.396 (3)
O6—C13	1.216 (2)	C9—C14	1.517 (2)
O7—C14	1.240 (2)	C10—C11	1.382 (2)
O8—C14	1.268 (2)	C10—H10	0.9500
O8—In1^i	2.1152 (12)	C11—C12	1.383 (3)
O9—H91	0.8400	C11—H11	0.9500
O9—H92	0.8400	C12—H12	0.9500
N1—C5	1.343 (2)	O10—H101	0.8400
N1—C1	1.345 (2)	O10—H102	0.8400
N2—C12	1.339 (2)	O11—H111	0.8400
N2—C8	1.350 (2)	O11—H112	0.8400
O8^i—In1—O1	83.58 (5)	C2—C3—H3	120.0
O8^i—In1—O9	84.44 (5)	C5—C4—C3	119.06 (17)
O1—In1—O9	101.63 (5)	C5—C4—H4	120.5
O8^i—In1—O5	104.07 (5)	C3—C4—H4	120.5
O1—In1—O5	165.16 (5)	N1—C5—C4	121.17 (16)
O9—In1—O5	91.87 (5)	N1—C5—H5	119.4
O8^i—In1—N2	97.32 (5)	C4—C5—H5	119.4
O1—In1—N2	91.20 (5)	O2—C6—O1	125.21 (17)
O9—In1—N2	167.17 (5)	O2—C6—C1	119.13 (15)
O5—In1—N2	75.36 (5)	O1—C6—C1	115.64 (14)
O8^i—In1—N1	153.16 (5)	O3—C7—O4	124.16 (16)
O1—In1—N1	75.34 (5)	O3—C7—C2	121.80 (15)
O9—In1—N1	83.75 (5)	O4—C7—C2	113.89 (15)
O5—In1—N1	100.33 (5)	N2—C8—C9	121.27 (16)
N2—In1—N1	99.52 (5)	N2—C8—C13	115.55 (15)
C6—O1—In1	119.19 (11)	C9—C8—C13	123.18 (15)
C7—O4—H4O	112.4	C8—C9—C10	118.45 (16)
C13—O5—In1	118.93 (11)	C8—C9—C14	123.82 (16)
C14—O8—In1^i	140.24 (11)	C10—C9—C14	117.73 (16)
In1—O9—H91	121.2	C11—C10—C9	119.83 (18)
In1—O9—H92	112.4	C11—C10—H10	120.1
H91—O9—H92	117.5	C9—C10—H10	120.1
C5—N1—C1	120.12 (15)	C10—C11—C12	118.58 (18)
C5—N1—In1	126.80 (11)	C10—C11—H11	120.7
C1—N1—In1	111.76 (11)	C12—C11—H11	120.7
C12—N2—C8	119.97 (16)	N2—C12—C11	121.89 (16)
C12—N2—In1	126.11 (11)	N2—C12—H12	119.1
C8—N2—In1	113.89 (12)	C11—C12—H12	119.1
N1—C1—C2	121.65 (16)	O6—C13—O5	124.90 (17)
N1—C1—C6	115.19 (15)	O6—C13—C8	119.05 (16)
C2—C1—C6	123.09 (15)	O5—C13—C8	116.05 (14)
C1—C2—C3	118.00 (16)	O7—C14—O8	123.27 (15)
C1—C2—C7	122.31 (16)	O7—C14—C9	117.88 (15)
C3—C2—C7	119.33 (16)	O8—C14—C9	118.63 (15)
C4—C3—C2	119.91 (17)	H101—O10—H102	105.0
C4—C3—H3	120.0	H111—O11—H112	111.8
O8^i—In1—O1—C6	162.67 (13)	C2—C3—C4—C5	−2.0 (3)
O9—In1—O1—C6	79.72 (13)	C1—N1—C5—C4	−0.1 (3)
O5—In1—O1—C6	−75.3 (2)	In1—N1—C5—C4	−165.89 (13)
N2—In1—O1—C6	−100.10 (13)	C3—C4—C5—N1	2.5 (3)
N1—In1—O1—C6	−0.57 (12)	In1—O1—C6—O2	169.57 (14)
O8^i—In1—O5—C13	89.72 (12)	In1—O1—C6—C1	−8.69 (19)
O1—In1—O5—C13	−30.0 (2)	N1—C1—C6—O2	−159.83 (16)
O9—In1—O5—C13	174.45 (12)	C2—C1—C6—O2	16.9 (3)
N2—In1—O5—C13	−4.31 (11)	N1—C1—C6—O1	18.5 (2)
N1—In1—O5—C13	−101.56 (12)	C2—C1—C6—O1	−164.68 (16)
O8^i—In1—N1—C5	138.04 (14)	C1—C2—C7—O3	53.6 (3)
O1—In1—N1—C5	177.42 (15)	C3—C2—C7—O3	−119.3 (2)
O9—In1—N1—C5	73.64 (15)	C1—C2—C7—O4	−130.59 (18)
O5—In1—N1—C5	−17.12 (15)	C3—C2—C7—O4	56.5 (2)
N2—In1—N1—C5	−93.83 (15)	C12—N2—C8—C9	−0.6 (2)
O8^i—In1—N1—C1	−28.73 (19)	In1—N2—C8—C9	177.46 (12)
O1—In1—N1—C1	10.65 (11)	C12—N2—C8—C13	179.38 (15)
O9—In1—N1—C1	−93.12 (12)	In1—N2—C8—C13	−2.56 (18)
O5—In1—N1—C1	176.11 (12)	N2—C8—C9—C10	0.9 (2)
N2—In1—N1—C1	99.40 (12)	C13—C8—C9—C10	−179.06 (16)
O8^i—In1—N2—C12	78.74 (14)	N2—C8—C9—C14	−179.73 (16)
O1—In1—N2—C12	−4.94 (14)	C13—C8—C9—C14	0.3 (3)
O9—In1—N2—C12	175.85 (19)	C8—C9—C10—C11	−0.5 (3)
O5—In1—N2—C12	−178.56 (15)	C14—C9—C10—C11	−179.94 (16)
N1—In1—N2—C12	−80.27 (14)	C9—C10—C11—C12	−0.1 (3)
O8^i—In1—N2—C8	−99.18 (12)	C8—N2—C12—C11	−0.1 (3)
O1—In1—N2—C8	177.14 (12)	In1—N2—C12—C11	−177.90 (13)
O9—In1—N2—C8	−2.1 (3)	C10—C11—C12—N2	0.4 (3)
O5—In1—N2—C8	3.52 (11)	In1—O5—C13—O6	−174.77 (13)
N1—In1—N2—C8	101.80 (12)	In1—O5—C13—C8	4.34 (18)
C5—N1—C1—C2	−2.7 (3)	N2—C8—C13—O6	178.18 (15)
In1—N1—C1—C2	165.07 (13)	C9—C8—C13—O6	−1.8 (3)
C5—N1—C1—C6	174.13 (15)	N2—C8—C13—O5	−1.0 (2)
In1—N1—C1—C6	−18.10 (17)	C9—C8—C13—O5	179.00 (15)
N1—C1—C2—C3	3.0 (3)	In1^i—O8—C14—O7	−176.98 (13)
C6—C1—C2—C3	−173.52 (16)	In1^i—O8—C14—C9	−2.6 (3)
N1—C1—C2—C7	−169.95 (16)	C8—C9—C14—O7	−93.8 (2)
C6—C1—C2—C7	13.5 (3)	C10—C9—C14—O7	85.6 (2)
C1—C2—C3—C4	−0.7 (3)	C8—C9—C14—O8	91.5 (2)
C7—C2—C3—C4	172.56 (17)	C10—C9—C14—O8	−89.1 (2)

Symmetry code: (i) −x+2, −y+2, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H91···O11^ii	0.84	1.75	2.5938 (19)	178
O9—H92···O3^ii	0.84	1.80	2.6402 (17)	175
O11—H112···O7^iii	0.84	1.95	2.7595 (18)	162
O10—H101···O5^iv	0.84	1.97	2.8065 (18)	175
O10—H102···O7^v	0.84	1.88	2.7237 (19)	178
O4—H4O···O10	0.84	1.67	2.5124 (17)	178
C4—H4···O1^vi	0.95	2.35	3.231 (2)	154
C5—H5···O6^vii	0.95	2.36	3.293 (2)	168
C11—H11···O3^viii	0.95	2.61	3.495 (2)	156
C12—H12···O2^viii	0.95	2.33	2.993 (2)	126

Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z−1; (iv) x, y, z−1; (v) −x+1, −y+2, −z+1; (vi) x−1, y, z; (vii) −x+1, −y+2, −z+2; (viii) −x+2, −y+2, −z+1.