Tris­(quinolin-8-olato)­indium(III)

The single-crystal structure of the title compound, [In(C₉H₆NO)₃], is described. Quinolinolates of the elements of the group IIIB (denoted by MQ₃), Al, Ga, and In, have been of continuous interest to organometallic and physical chemists, in particular, for the last 50 years. Organic light-emitting diodes (OLEDs) utilizing GaQ₃ and InQ₃, the gallium and indium analogs, respectively, of the most widely used OLED material AlQ₃, were first explored in the early 1980s and continue to be the subject of current research. To the best of our knowledge, the structure reported here is the first-ever facial MQ₃-type structure, confirmed by single-crystal X-ray crystallography.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.050
• wR factor = 0.150
• Data-to-parameter ratio = 15.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



GOODF_01  Alert C The least squares goodness of fit parameter lies
          outside the range 0.80 <> 2.00
          Goodness of fit given =      0.743

RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.112

PLAT_601  Alert C Structure Contains Solvent Accessible VOIDS of      36.00 A   3

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      0.944
          Tmax scaled      0.936 Tmin scaled      0.488


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 3 Alert Level C = Please check

---

S1. Comment

In 1987, efficient electroluminescence from an organic light-emitting diode (OLED) device using low molecular weight organic materials was first reported (Tang & Van Slyke, 1987). Their device was constructed of two active layers and used the metal–quinolinolate tris(8-hydroxyquinoline)aluminium. This discovery generated renewed interest in metal quinolinolates. The tris-chelate 8-hydroxyquinoline metal complexes can occur in two different geometrical forms, viz. facial or meridional. To date, all published Alq₃ single-crystal structures (including different polymorphs and solvates) and Gaq₃ structures were found to be meridional isomers (Brinkmann et al., 2000; Ul-Haque et al., 1991; Fujii et al., 1996; Wang et al., 1999). Single-crystal structures of facial isomers of Meq₃-type complexes have been elusive so far. We report here the crystal structure of the title compound, Inq₃, (I).

The molecular structure of Inq₃ (Fig. 1) is a six-coordinated indium compound. The angles around the In atom indicate approximate octahedral geometry. The average In—O and In—N distances are 2.108 and 2.261 Å, respectively. There is intermolecular π–π stacking of the ligands (8-hydroxyquinolines) in a multidirectional fashion. Such intermolecular stacking was also observed in the Gaq₃ structure (Wang et al., 1999). The ligands in Inq₃ are stacked in a unit cell with interplanar distances in the range 3.406–3.428 Å, which is comparable to 3.35–3.41 Å for Gaq₃ (Fig. 2).

S2. Experimental

Inq₃ was synthesized according to established methods (Lytle et al., 1973). Inq₃ was chemically purified by washing and recrystallization and subjected to vacuum temperature-gradient sublimation three consecutive times until the purity of 99.9% was achieved. The purity was determined by NMR in d₆-DMSO. We note that although the remaining impurities could not be positively characterized, they could consist of different forms, e.g. isomers or polymorphs, of the target compound. Inq₃ was sublimed at 0.6 Torr and the temperature was gradually increased from 533 to 573 K over a period of 1–3 d. It was also characterized by HPLC, LC—MS, and ESIMS, showing results consistent with structure and purity determined by NMR.

S3. Refinement

The quality of the Inq₃ crystals was not superior as indicated by a rather high R_int (0.1115) value. There was a minor twin component in the crystals, which was left untreated. During subsequent refinement, positional parameters of H atoms were calculated geometrically and allowed to ride on the C atoms to which they were bonded.

Computing details

Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001) and Materials Studio (Accelrys, 2001); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. A view of the molecule of the title compound, (I), showing the atomic numbering scheme. Displacement ellipsoids were drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of Inq3, illustrating the stacking of 8-hydroxyquinoline ligands. Stacking distances along various planes are indicated.

Tris(quinolin-8-olato)indium

Crystal data

[In(C9H6NO)3]	Z = 2
Mr = 547.26	F(000) = 548
Triclinic, P1	Dx = 1.641 Mg m^−3
a = 6.1860 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.436 (3) Å	Cell parameters from 10088 reflections
c = 14.725 (3) Å	θ = 1.0–26.7°
α = 65.63 (3)°	µ = 1.10 mm^−1
β = 88.15 (3)°	T = 293 K
γ = 83.55 (3)°	Needle, yellow
V = 1107.7 (4) Å^3	0.6 × 0.07 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer	4647 independent reflections
Radiation source: fine-focus sealed tube	2896 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	Rint = 0.112
Detector resolution: 9 pixels mm^-1	θmax = 26.8°, θmin = 4.0°
ϕ and ω scans	h = −7→7
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −16→15
Tmin = 0.517, Tmax = 0.991	l = −18→14
11360 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.150	H-atom parameters constrained
S = 0.74	w = 1/[σ^2(Fo^2) + (0.1127P)^2] where P = (Fo^2 + 2Fc^2)/3
4647 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.59 e Å^−3
0 restraints	Δρmin = −1.05 e Å^−3

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	0.78291 (5)	0.80366 (3)	0.31744 (3)	0.03885 (18)
O1	0.9653 (6)	0.7401 (4)	0.2257 (3)	0.0514 (11)
O2	0.9104 (6)	0.9563 (4)	0.2681 (3)	0.0501 (11)
O3	0.9595 (6)	0.7262 (4)	0.4526 (3)	0.0512 (11)
N1	0.6030 (7)	0.6614 (4)	0.3284 (4)	0.0410 (11)
N2	0.5482 (6)	0.9168 (4)	0.1931 (3)	0.0392 (11)
N3	0.5591 (7)	0.8395 (4)	0.4263 (4)	0.0422 (12)
C1	0.6892 (9)	0.6190 (5)	0.2638 (4)	0.0422 (14)
C2	0.8812 (9)	0.6640 (5)	0.2103 (4)	0.0463 (15)
C3	0.9621 (11)	0.6197 (6)	0.1446 (5)	0.0595 (18)
H3	1.0866	0.6446	0.1091	0.071*
C4	0.8643 (14)	0.5394 (7)	0.1296 (6)	0.072 (2)
H4	0.9241	0.5130	0.0840	0.087*
C5	0.6841 (13)	0.4984 (6)	0.1796 (6)	0.068 (2)
H5	0.6211	0.4452	0.1676	0.082*
C6	0.5931 (11)	0.5365 (6)	0.2492 (5)	0.0565 (17)
C7	0.4094 (11)	0.4974 (6)	0.3076 (6)	0.0633 (19)
H7	0.3429	0.4420	0.3010	0.076*
C8	0.3303 (10)	0.5379 (6)	0.3713 (6)	0.0620 (19)
H8	0.2107	0.5108	0.4099	0.074*
C9	0.4303 (9)	0.6227 (5)	0.3799 (5)	0.0511 (16)
H9	0.3723	0.6525	0.4234	0.061*
C10	0.6005 (8)	1.0214 (5)	0.1571 (4)	0.0386 (13)
C11	0.7928 (9)	1.0398 (5)	0.1984 (4)	0.0427 (14)
C12	0.8476 (11)	1.1470 (6)	0.1617 (5)	0.0577 (17)
H12	0.9707	1.1618	0.1865	0.069*
C13	0.7189 (13)	1.2328 (6)	0.0877 (6)	0.068 (2)
H13	0.7596	1.3036	0.0646	0.082*
C14	0.5351 (13)	1.2167 (7)	0.0480 (6)	0.069 (2)
H14	0.4519	1.2755	−0.0005	0.083*
C15	0.4752 (10)	1.1093 (6)	0.0822 (4)	0.0508 (16)
C16	0.2919 (10)	1.0823 (7)	0.0459 (5)	0.061 (2)
H16	0.2037	1.1373	−0.0035	0.074*
C17	0.2436 (10)	0.9774 (7)	0.0823 (5)	0.0605 (19)
H17	0.1238	0.9597	0.0577	0.073*
C18	0.3754 (8)	0.8964 (5)	0.1569 (4)	0.0455 (15)
H18	0.3398	0.8245	0.1823	0.055*
C19	0.6566 (8)	0.8026 (5)	0.5172 (4)	0.0400 (14)
C20	0.8694 (9)	0.7425 (5)	0.5283 (4)	0.0424 (14)
C21	0.9677 (10)	0.7041 (6)	0.6215 (5)	0.0548 (17)
H21	1.1032	0.6630	0.6331	0.066*
C22	0.8651 (13)	0.7264 (6)	0.6989 (5)	0.064 (2)
H22	0.9373	0.7000	0.7602	0.077*
C23	0.6666 (13)	0.7844 (6)	0.6886 (5)	0.0622 (19)
H23	0.6047	0.7976	0.7415	0.075*
C24	0.5557 (10)	0.8241 (5)	0.5963 (5)	0.0474 (15)
C25	0.3491 (11)	0.8844 (6)	0.5765 (6)	0.064 (2)
H25	0.2765	0.9002	0.6261	0.076*
C26	0.2561 (10)	0.9194 (7)	0.4852 (6)	0.064 (2)
H26	0.1197	0.9598	0.4720	0.077*
C27	0.3628 (8)	0.8955 (5)	0.4107 (5)	0.0495 (16)
H27	0.2952	0.9192	0.3487	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
In1	0.0294 (2)	0.0494 (3)	0.0378 (3)	−0.00411 (16)	−0.00044 (15)	−0.0180 (2)
O1	0.042 (2)	0.062 (3)	0.057 (3)	−0.013 (2)	0.0149 (19)	−0.030 (2)
O2	0.040 (2)	0.058 (3)	0.052 (3)	−0.0154 (19)	−0.0029 (19)	−0.020 (2)
O3	0.035 (2)	0.068 (3)	0.046 (3)	0.0054 (18)	−0.0069 (18)	−0.022 (2)
N1	0.037 (2)	0.041 (3)	0.043 (3)	−0.005 (2)	0.004 (2)	−0.015 (2)
N2	0.032 (2)	0.048 (3)	0.037 (3)	−0.006 (2)	−0.0013 (19)	−0.016 (2)
N3	0.039 (2)	0.049 (3)	0.043 (3)	−0.002 (2)	0.003 (2)	−0.024 (3)
C1	0.047 (3)	0.036 (3)	0.034 (3)	−0.002 (2)	−0.007 (2)	−0.005 (3)
C2	0.044 (3)	0.053 (4)	0.038 (3)	0.009 (3)	−0.003 (3)	−0.018 (3)
C3	0.070 (4)	0.055 (5)	0.050 (4)	0.008 (3)	0.003 (3)	−0.021 (4)
C4	0.110 (6)	0.058 (5)	0.052 (5)	0.014 (5)	−0.005 (4)	−0.032 (4)
C5	0.086 (5)	0.052 (5)	0.071 (5)	0.000 (4)	−0.017 (4)	−0.030 (4)
C6	0.064 (4)	0.047 (4)	0.057 (4)	−0.001 (3)	−0.011 (3)	−0.019 (4)
C7	0.069 (4)	0.043 (4)	0.071 (5)	−0.014 (3)	−0.016 (4)	−0.014 (4)
C8	0.050 (4)	0.053 (5)	0.071 (5)	−0.015 (3)	0.001 (3)	−0.012 (4)
C9	0.041 (3)	0.054 (4)	0.054 (4)	−0.008 (3)	0.004 (3)	−0.017 (3)
C10	0.039 (3)	0.046 (4)	0.032 (3)	−0.003 (2)	0.007 (2)	−0.018 (3)
C11	0.045 (3)	0.049 (4)	0.038 (3)	−0.010 (3)	0.010 (3)	−0.021 (3)
C12	0.068 (4)	0.060 (5)	0.058 (4)	−0.020 (3)	0.018 (3)	−0.034 (4)
C13	0.098 (6)	0.049 (5)	0.058 (5)	−0.017 (4)	0.027 (4)	−0.022 (4)
C14	0.085 (5)	0.061 (5)	0.048 (4)	0.008 (4)	0.008 (4)	−0.013 (4)
C15	0.053 (3)	0.058 (5)	0.032 (3)	0.007 (3)	0.005 (3)	−0.013 (3)
C16	0.047 (4)	0.084 (6)	0.039 (4)	0.012 (3)	−0.003 (3)	−0.015 (4)
C17	0.041 (3)	0.088 (6)	0.046 (4)	−0.007 (3)	−0.004 (3)	−0.022 (4)
C18	0.041 (3)	0.056 (4)	0.036 (3)	−0.009 (3)	−0.003 (2)	−0.015 (3)
C19	0.035 (3)	0.043 (4)	0.043 (3)	−0.012 (2)	0.003 (2)	−0.016 (3)
C20	0.043 (3)	0.041 (4)	0.041 (4)	−0.014 (2)	0.001 (3)	−0.013 (3)
C21	0.049 (3)	0.058 (4)	0.047 (4)	−0.007 (3)	−0.013 (3)	−0.010 (3)
C22	0.098 (6)	0.056 (5)	0.039 (4)	−0.032 (4)	−0.011 (4)	−0.013 (4)
C23	0.090 (5)	0.060 (5)	0.044 (4)	−0.032 (4)	0.015 (4)	−0.024 (4)
C24	0.057 (4)	0.048 (4)	0.044 (4)	−0.022 (3)	0.013 (3)	−0.022 (3)
C25	0.063 (4)	0.080 (6)	0.068 (5)	−0.022 (4)	0.025 (4)	−0.048 (5)
C26	0.045 (3)	0.081 (6)	0.076 (5)	−0.009 (3)	0.018 (3)	−0.043 (5)
C27	0.030 (3)	0.062 (4)	0.060 (4)	−0.003 (3)	−0.001 (3)	−0.028 (4)

Geometric parameters (Å, º)

In1—O3	2.101 (4)	C6—C7	1.416 (10)
In1—O2	2.110 (4)	C7—C8	1.322 (10)
In1—O1	2.112 (4)	C8—C9	1.406 (9)
In1—N3	2.250 (5)	C10—C15	1.409 (8)
In1—N1	2.264 (5)	C10—C11	1.443 (7)
In1—N2	2.269 (4)	C11—C12	1.392 (9)
O1—C2	1.298 (8)	C12—C13	1.401 (10)
O2—C11	1.325 (7)	C13—C14	1.373 (10)
O3—C20	1.317 (7)	C14—C15	1.408 (10)
N1—C9	1.316 (7)	C15—C16	1.412 (9)
N1—C1	1.365 (8)	C16—C17	1.351 (10)
N2—C18	1.314 (7)	C17—C18	1.389 (9)
N2—C10	1.355 (8)	C19—C24	1.420 (8)
N3—C27	1.328 (7)	C19—C20	1.442 (8)
N3—C19	1.356 (7)	C20—C21	1.385 (8)
C1—C6	1.407 (9)	C21—C22	1.409 (10)
C1—C2	1.451 (8)	C22—C23	1.356 (10)
C2—C3	1.386 (9)	C23—C24	1.408 (9)
C3—C4	1.389 (10)	C24—C25	1.404 (9)
C4—C5	1.356 (11)	C25—C26	1.352 (11)
C5—C6	1.401 (10)	C26—C27	1.392 (9)
O3—In1—O2	96.96 (17)	C1—C6—C5	118.7 (7)
O3—In1—O1	101.69 (17)	C1—C6—C7	116.7 (7)
O2—In1—O1	98.33 (17)	C5—C6—C7	124.6 (7)
O3—In1—N3	76.88 (16)	C8—C7—C6	121.5 (7)
O2—In1—N3	93.12 (18)	C7—C8—C9	118.8 (7)
O1—In1—N3	168.54 (17)	N1—C9—C8	122.4 (7)
O3—In1—N1	98.64 (17)	N2—C10—C15	122.2 (5)
O2—In1—N1	164.31 (16)	N2—C10—C11	117.1 (5)
O1—In1—N1	76.89 (17)	C15—C10—C11	120.7 (6)
N3—In1—N1	92.01 (17)	O2—C11—C12	122.5 (6)
O3—In1—N2	163.81 (17)	O2—C11—C10	120.1 (5)
O2—In1—N2	76.89 (16)	C12—C11—C10	117.4 (6)
O1—In1—N2	94.06 (17)	C11—C12—C13	120.6 (7)
N3—In1—N2	88.41 (17)	C14—C13—C12	122.7 (7)
N1—In1—N2	88.45 (17)	C13—C14—C15	118.6 (7)
C2—O1—In1	115.4 (3)	C10—C15—C14	120.0 (6)
C11—O2—In1	115.2 (3)	C10—C15—C16	116.3 (6)
C20—O3—In1	115.2 (3)	C14—C15—C16	123.7 (6)
C9—N1—C1	119.5 (5)	C17—C16—C15	120.6 (6)
C9—N1—In1	130.5 (4)	C16—C17—C18	119.0 (6)
C1—N1—In1	109.8 (3)	N2—C18—C17	122.9 (6)
C18—N2—C10	119.0 (5)	N3—C19—C24	121.6 (5)
C18—N2—In1	130.4 (4)	N3—C19—C20	116.3 (5)
C10—N2—In1	110.5 (3)	C24—C19—C20	122.1 (5)
C27—N3—C19	119.6 (5)	O3—C20—C21	123.6 (5)
C27—N3—In1	129.2 (4)	O3—C20—C19	120.3 (5)
C19—N3—In1	111.0 (3)	C21—C20—C19	116.1 (6)
N1—C1—C6	121.1 (6)	C20—C21—C22	120.9 (6)
N1—C1—C2	116.9 (5)	C23—C22—C21	123.2 (6)
C6—C1—C2	122.0 (6)	C22—C23—C24	118.8 (7)
O1—C2—C3	124.6 (6)	C23—C24—C25	124.2 (6)
O1—C2—C1	120.3 (5)	C23—C24—C19	118.8 (6)
C3—C2—C1	115.1 (6)	C25—C24—C19	117.0 (6)
C4—C3—C2	122.5 (7)	C26—C25—C24	119.8 (6)
C5—C4—C3	121.9 (7)	C25—C26—C27	120.5 (6)
C4—C5—C6	119.8 (7)	N3—C27—C26	121.4 (6)
O3—In1—O1—C2	103.6 (4)	C2—C1—C6—C7	178.5 (5)
O2—In1—O1—C2	−157.5 (4)	C4—C5—C6—C1	1.5 (10)
N3—In1—O1—C2	22.0 (10)	C4—C5—C6—C7	−178.1 (7)
N1—In1—O1—C2	7.3 (4)	C1—C6—C7—C8	1.1 (9)
N2—In1—O1—C2	−80.1 (4)	C5—C6—C7—C8	−179.2 (7)
O3—In1—O2—C11	−160.7 (4)	C6—C7—C8—C9	0.8 (10)
O1—In1—O2—C11	96.4 (4)	C1—N1—C9—C8	0.4 (9)
N3—In1—O2—C11	−83.5 (4)	In1—N1—C9—C8	174.9 (4)
N1—In1—O2—C11	25.4 (8)	C7—C8—C9—N1	−1.7 (10)
N2—In1—O2—C11	4.1 (4)	C18—N2—C10—C15	0.3 (8)
O2—In1—O3—C20	86.5 (4)	In1—N2—C10—C15	−177.2 (4)
O1—In1—O3—C20	−173.5 (4)	C18—N2—C10—C11	−179.4 (5)
N3—In1—O3—C20	−5.1 (4)	In1—N2—C10—C11	3.1 (6)
N1—In1—O3—C20	−95.2 (4)	In1—O2—C11—C12	176.4 (5)
N2—In1—O3—C20	20.0 (8)	In1—O2—C11—C10	−4.0 (7)
O3—In1—N1—C9	78.4 (5)	N2—C10—C11—O2	0.3 (8)
O2—In1—N1—C9	−107.7 (7)	C15—C10—C11—O2	−179.4 (5)
O1—In1—N1—C9	178.5 (5)	N2—C10—C11—C12	180.0 (5)
N3—In1—N1—C9	1.4 (5)	C15—C10—C11—C12	0.3 (8)
N2—In1—N1—C9	−87.0 (5)	O2—C11—C12—C13	179.8 (6)
O3—In1—N1—C1	−106.6 (4)	C10—C11—C12—C13	0.2 (9)
O2—In1—N1—C1	67.3 (7)	C11—C12—C13—C14	0.1 (11)
O1—In1—N1—C1	−6.5 (3)	C12—C13—C14—C15	−0.8 (11)
N3—In1—N1—C1	176.3 (4)	N2—C10—C15—C14	179.3 (6)
N2—In1—N1—C1	88.0 (4)	C11—C10—C15—C14	−1.0 (9)
O3—In1—N2—C18	−111.8 (7)	N2—C10—C15—C16	−0.5 (8)
O2—In1—N2—C18	179.1 (5)	C11—C10—C15—C16	179.2 (5)
O1—In1—N2—C18	81.5 (5)	C13—C14—C15—C10	1.2 (10)
N3—In1—N2—C18	−87.3 (5)	C13—C14—C15—C16	−179.0 (6)
N1—In1—N2—C18	4.7 (5)	C10—C15—C16—C17	−0.1 (9)
O3—In1—N2—C10	65.3 (7)	C14—C15—C16—C17	−179.9 (7)
O2—In1—N2—C10	−3.8 (4)	C15—C16—C17—C18	0.8 (10)
O1—In1—N2—C10	−101.4 (4)	C10—N2—C18—C17	0.5 (9)
N3—In1—N2—C10	89.8 (4)	In1—N2—C18—C17	177.4 (5)
N1—In1—N2—C10	−178.2 (4)	C16—C17—C18—N2	−1.0 (10)
O3—In1—N3—C27	−179.9 (5)	C27—N3—C19—C24	−1.2 (9)
O2—In1—N3—C27	83.7 (5)	In1—N3—C19—C24	174.3 (4)
O1—In1—N3—C27	−95.8 (9)	C27—N3—C19—C20	180.0 (5)
N1—In1—N3—C27	−81.5 (5)	In1—N3—C19—C20	−4.5 (6)
N2—In1—N3—C27	6.9 (5)	In1—O3—C20—C21	−175.8 (5)
O3—In1—N3—C19	5.1 (4)	In1—O3—C20—C19	4.6 (7)
O2—In1—N3—C19	−91.3 (4)	N3—C19—C20—O3	0.3 (8)
O1—In1—N3—C19	89.2 (8)	C24—C19—C20—O3	−178.6 (5)
N1—In1—N3—C19	103.5 (4)	N3—C19—C20—C21	−179.4 (5)
N2—In1—N3—C19	−168.1 (4)	C24—C19—C20—C21	1.7 (8)
C9—N1—C1—C6	1.7 (8)	O3—C20—C21—C22	178.5 (6)
In1—N1—C1—C6	−173.9 (4)	C19—C20—C21—C22	−1.8 (9)
C9—N1—C1—C2	−179.2 (5)	C20—C21—C22—C23	0.9 (11)
In1—N1—C1—C2	5.2 (6)	C21—C22—C23—C24	0.3 (10)
In1—O1—C2—C3	172.9 (5)	C22—C23—C24—C25	179.6 (6)
In1—O1—C2—C1	−7.2 (7)	C22—C23—C24—C19	−0.4 (9)
N1—C1—C2—O1	0.9 (8)	N3—C19—C24—C23	−179.4 (6)
C6—C1—C2—O1	180.0 (5)	C20—C19—C24—C23	−0.6 (9)
N1—C1—C2—C3	−179.2 (5)	N3—C19—C24—C25	0.6 (9)
C6—C1—C2—C3	−0.1 (8)	C20—C19—C24—C25	179.4 (6)
O1—C2—C3—C4	−179.0 (6)	C23—C24—C25—C26	179.8 (7)
C1—C2—C3—C4	1.1 (9)	C19—C24—C25—C26	−0.2 (10)
C2—C3—C4—C5	−0.8 (11)	C24—C25—C26—C27	0.5 (11)
C3—C4—C5—C6	−0.6 (11)	C19—N3—C27—C26	1.4 (9)
N1—C1—C6—C5	177.9 (5)	In1—N3—C27—C26	−173.2 (5)
C2—C1—C6—C5	−1.2 (9)	C25—C26—C27—N3	−1.0 (11)
N1—C1—C6—C7	−2.4 (8)