Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803009231/ac6038sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803009231/ac6038Isup2.hkl |
CCDC reference: 214768
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.
The quality of the Inq3 crystals was not superior as indicated by a rather high Rint (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.
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.
[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) Å3 | 0.6 × 0.07 × 0.06 mm |
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 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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 0.74 | w = 1/[σ2(Fo2) + (0.1127P)2] where P = (Fo2 + 2Fc2)/3 |
4647 reflections | (Δ/σ)max < 0.001 |
307 parameters | Δρmax = 0.59 e Å−3 |
0 restraints | Δρmin = −1.05 e Å−3 |
[In(C9H6NO)3] | γ = 83.55 (3)° |
Mr = 547.26 | V = 1107.7 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.1860 (12) Å | Mo Kα radiation |
b = 13.436 (3) Å | µ = 1.10 mm−1 |
c = 14.725 (3) Å | T = 293 K |
α = 65.63 (3)° | 0.6 × 0.07 × 0.06 mm |
β = 88.15 (3)° |
Nonius KappaCCD diffractometer | 4647 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 2896 reflections with I > 2σ(I) |
Tmin = 0.517, Tmax = 0.991 | Rint = 0.112 |
11360 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 0.74 | Δρmax = 0.59 e Å−3 |
4647 reflections | Δρmin = −1.05 e Å−3 |
307 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
Experimental details
Crystal data | |
Chemical formula | [In(C9H6NO)3] |
Mr | 547.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 6.1860 (12), 13.436 (3), 14.725 (3) |
α, β, γ (°) | 65.63 (3), 88.15 (3), 83.55 (3) |
V (Å3) | 1107.7 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.10 |
Crystal size (mm) | 0.6 × 0.07 × 0.06 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.517, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11360, 4647, 2896 |
Rint | 0.112 |
(sin θ/λ)max (Å−1) | 0.634 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.150, 0.74 |
No. of reflections | 4647 |
No. of parameters | 307 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.59, −1.05 |
Computer programs: COLLECT (Nonius, 1997-2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001) and Materials Studio (Accelrys, 2001), SHELXTL.
In1—O3 | 2.101 (4) | In1—N3 | 2.250 (5) |
In1—O2 | 2.110 (4) | In1—N1 | 2.264 (5) |
In1—O1 | 2.112 (4) | In1—N2 | 2.269 (4) |
O3—In1—O2 | 96.96 (17) | O1—In1—N1 | 76.89 (17) |
O3—In1—O1 | 101.69 (17) | N3—In1—N1 | 92.01 (17) |
O2—In1—O1 | 98.33 (17) | O3—In1—N2 | 163.81 (17) |
O3—In1—N3 | 76.88 (16) | O2—In1—N2 | 76.89 (16) |
O2—In1—N3 | 93.12 (18) | O1—In1—N2 | 94.06 (17) |
O1—In1—N3 | 168.54 (17) | N3—In1—N2 | 88.41 (17) |
O3—In1—N1 | 98.64 (17) | N1—In1—N2 | 88.45 (17) |
O2—In1—N1 | 164.31 (16) |
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).