Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049136/sj2354sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049136/sj2354Isup2.hkl |
CCDC reference: 655864
1-propylquinolinium iodide was prepared as reported in literature (Huang et al., 1988). 1-propylquinolinium iodide (0.30 g, 1.0 mmol) and CuI (0.19 g, 1 mmol) were dissolved in 15 mL DMF and stirred for 20 min to give a clear red solution which was filtered and allowed to evaporate at room temperature. Red block-like crystals formed over one, week in 65% yield. (0.32 g). Calcd. For C24H28CuI3N2 (788.73): C, 36.40 H, 3.52 N, 3.53% Found: C, 36.51 H, 3.55 N, 3.55%.
All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å for aromatic H atoms 0.97 Å for methylene H atoms and 0.96 Å for methyl H atoms, respectively, and with Uiso(H) = 1.2Ueq(C) for aromatic and methylene H atoms, Uiso(H) = 1.5Ueq(C) for methyl H atoms.
In the title compound, (I) Fig. 1, the asymmetric unit contains two N-propylquinolinium cations which lie on opposite sides of the CuI32- anion. In the anion cluster, Cu—I bond distances lie in the range from 2.5161 (13) Å to 2.5529 (12)Å and the I1—Cu—I2, I2—Cu—I3 and I1—Cu—I3 bond angles are 124.29°, 117.02° and 118.69°, respectively. All of the atoms in the anion are essentially coplanar with an rms deviation from the [CuI3]2- mean plane of 0.0001|%A. The inorganic and organic components are linked via C—H···I hydrogen bonds to give a 3-dimensional network, Table 1. The cations are further aggregated through π-π stacking interactions with centroid to centroid distances of 3.48 (7)Å and 3.43 (5)Å respectively between the quinolinium rings, Fig 2.
For information on C—H···I hydrogen bonds, see Horn et al., 2003 and on π–π stacking, see Robin et al., 2001 Reference not in list – should this be Robin & Fromm (2006)?. For related literature, see: Huang & Xie (1988); Robin & Fromm (2006).
Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY (Molecular Structure Corporation, 1999); data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. The structure of (I) showing the atom numbering with ellipsoids drawn at the 50% probability level. | |
Fig. 2. Crystal packing for (I) with hydrogen bonds drawn as dashed lines. |
(C12H14N)2[CuI3] | Z = 2 |
Mr = 788.73 | F(000) = 748.0 |
Triclinic, P1 | Dx = 1.945 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4373 (19) Å | Cell parameters from 18 reflections |
b = 9.5500 (19) Å | θ = 12–15° |
c = 16.175 (3) Å | µ = 4.26 mm−1 |
α = 81.27 (3)° | T = 293 K |
β = 76.03 (3)° | Block, red |
γ = 72.82 (3)° | 0.20 × 0.18 × 0.16 mm |
V = 1346.4 (5) Å3 |
Rigaku R-AXIS RAPID Imaging Plate diffractometer | 6176 independent reflections |
Radiation source: rotor target | 4121 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999) | h = −12→12 |
Tmin = 0.443, Tmax = 0.506 | k = −12→12 |
12812 measured reflections | l = −21→21 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.149 | w = 1/[σ2(Fo2) + (0.0369P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.87 | (Δ/σ)max = 0.001 |
6176 reflections | Δρmax = 0.69 e Å−3 |
273 parameters | Δρmin = −1.16 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0010 (2) |
(C12H14N)2[CuI3] | γ = 72.82 (3)° |
Mr = 788.73 | V = 1346.4 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.4373 (19) Å | Mo Kα radiation |
b = 9.5500 (19) Å | µ = 4.26 mm−1 |
c = 16.175 (3) Å | T = 293 K |
α = 81.27 (3)° | 0.20 × 0.18 × 0.16 mm |
β = 76.03 (3)° |
Rigaku R-AXIS RAPID Imaging Plate diffractometer | 6176 independent reflections |
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999) | 4121 reflections with I > 2σ(I) |
Tmin = 0.443, Tmax = 0.506 | Rint = 0.052 |
12812 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 0.87 | Δρmax = 0.69 e Å−3 |
6176 reflections | Δρmin = −1.16 e Å−3 |
273 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. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.55819 (5) | −0.00607 (5) | 0.24539 (3) | 0.05558 (16) | |
I2 | 0.40382 (5) | 0.46869 (5) | 0.18593 (3) | 0.05692 (16) | |
I3 | 0.09917 (5) | 0.25384 (6) | 0.36757 (3) | 0.06252 (17) | |
Cu1 | 0.35344 (9) | 0.23210 (9) | 0.26816 (5) | 0.0511 (2) | |
N2 | −0.2782 (5) | 0.2353 (6) | 0.5522 (3) | 0.0471 (12) | |
N1 | 0.8453 (5) | 0.2573 (6) | 0.0483 (3) | 0.0459 (11) | |
C1 | 0.8245 (8) | 0.2374 (8) | 0.1316 (5) | 0.0577 (17) | |
H1 | 0.7371 | 0.2131 | 0.1627 | 0.069* | |
C2 | 0.9279 (9) | 0.2515 (10) | 0.1745 (5) | 0.067 (2) | |
H2 | 0.9104 | 0.2371 | 0.2338 | 0.081* | |
C3 | 1.0563 (9) | 0.2868 (9) | 0.1292 (5) | 0.0648 (19) | |
H3 | 1.1266 | 0.2971 | 0.1578 | 0.078* | |
C4 | 1.0827 (7) | 0.3074 (7) | 0.0405 (5) | 0.0508 (15) | |
C5 | 1.2143 (8) | 0.3423 (8) | −0.0111 (6) | 0.0625 (19) | |
H5 | 1.2860 | 0.3564 | 0.0150 | 0.075* | |
C6 | 1.2376 (9) | 0.3554 (9) | −0.0963 (6) | 0.073 (2) | |
H6 | 1.3282 | 0.3712 | −0.1287 | 0.087* | |
C7 | 1.1263 (9) | 0.3454 (9) | −0.1371 (5) | 0.067 (2) | |
H7 | 1.1419 | 0.3597 | −0.1964 | 0.080* | |
C8 | 0.9949 (8) | 0.3150 (8) | −0.0912 (5) | 0.0538 (16) | |
H8 | 0.9211 | 0.3096 | −0.1188 | 0.065* | |
C9 | 0.9736 (6) | 0.2920 (6) | −0.0016 (4) | 0.0422 (13) | |
C10 | 0.7275 (7) | 0.2378 (7) | 0.0078 (4) | 0.0498 (15) | |
H10A | 0.7120 | 0.3132 | −0.0391 | 0.060* | |
H10B | 0.6325 | 0.2504 | 0.0494 | 0.060* | |
C11 | 0.7708 (8) | 0.0875 (8) | −0.0257 (5) | 0.0581 (17) | |
H11A | 0.8718 | 0.0690 | −0.0617 | 0.070* | |
H11B | 0.7723 | 0.0122 | 0.0219 | 0.070* | |
C12 | 0.6596 (10) | 0.0795 (10) | −0.0766 (7) | 0.080 (3) | |
H12A | 0.6887 | −0.0160 | −0.0973 | 0.119* | |
H12B | 0.6591 | 0.1532 | −0.1241 | 0.119* | |
H12C | 0.5600 | 0.0963 | −0.0407 | 0.119* | |
C13 | −0.3068 (8) | 0.1201 (8) | 0.5292 (5) | 0.0596 (18) | |
H13 | −0.2979 | 0.0339 | 0.5655 | 0.071* | |
C14 | −0.3501 (9) | 0.1256 (9) | 0.4519 (6) | 0.069 (2) | |
H14 | −0.3675 | 0.0432 | 0.4364 | 0.083* | |
C15 | −0.3662 (8) | 0.2494 (9) | 0.4005 (5) | 0.0636 (19) | |
H15 | −0.3962 | 0.2535 | 0.3493 | 0.076* | |
C16 | −0.3382 (7) | 0.3746 (8) | 0.4227 (4) | 0.0539 (16) | |
C17 | −0.3528 (8) | 0.5081 (11) | 0.3699 (5) | 0.070 (2) | |
H17 | −0.3844 | 0.5166 | 0.3188 | 0.084* | |
C18 | −0.3207 (9) | 0.6242 (9) | 0.3934 (6) | 0.071 (2) | |
H18 | −0.3310 | 0.7119 | 0.3585 | 0.085* | |
C19 | −0.2729 (9) | 0.6120 (9) | 0.4690 (6) | 0.070 (2) | |
H19 | −0.2492 | 0.6920 | 0.4832 | 0.084* | |
C20 | −0.2590 (7) | 0.4888 (8) | 0.5234 (5) | 0.0540 (16) | |
H20 | −0.2290 | 0.4847 | 0.5746 | 0.065* | |
C21 | −0.2914 (6) | 0.3660 (7) | 0.5004 (4) | 0.0405 (12) | |
C22 | −0.2312 (8) | 0.2202 (9) | 0.6344 (4) | 0.0589 (18) | |
H22A | −0.2700 | 0.1451 | 0.6725 | 0.071* | |
H22B | −0.2744 | 0.3124 | 0.6607 | 0.071* | |
C23 | −0.0588 (8) | 0.1787 (10) | 0.6223 (5) | 0.068 (2) | |
H23A | −0.0150 | 0.0869 | 0.5955 | 0.082* | |
H23B | −0.0196 | 0.2543 | 0.5850 | 0.082* | |
C24 | −0.0146 (11) | 0.1621 (15) | 0.7068 (7) | 0.104 (4) | |
H24A | 0.0939 | 0.1359 | 0.6984 | 0.157* | |
H24B | −0.0524 | 0.0863 | 0.7433 | 0.157* | |
H24C | −0.0569 | 0.2534 | 0.7328 | 0.157* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0505 (3) | 0.0452 (3) | 0.0663 (3) | −0.01132 (19) | −0.0080 (2) | −0.0006 (2) |
I2 | 0.0560 (3) | 0.0485 (3) | 0.0628 (3) | −0.0133 (2) | −0.0149 (2) | 0.0082 (2) |
I3 | 0.0488 (3) | 0.0813 (4) | 0.0485 (3) | −0.0122 (2) | −0.00168 (19) | −0.0029 (2) |
Cu1 | 0.0473 (4) | 0.0574 (5) | 0.0480 (5) | −0.0128 (4) | −0.0118 (3) | −0.0015 (4) |
N2 | 0.037 (2) | 0.055 (3) | 0.046 (3) | −0.012 (2) | −0.005 (2) | −0.001 (2) |
N1 | 0.039 (2) | 0.051 (3) | 0.046 (3) | −0.012 (2) | −0.008 (2) | −0.003 (2) |
C1 | 0.061 (4) | 0.064 (5) | 0.047 (4) | −0.020 (3) | −0.009 (3) | 0.004 (3) |
C2 | 0.075 (5) | 0.088 (6) | 0.040 (4) | −0.027 (4) | −0.016 (3) | 0.010 (4) |
C3 | 0.071 (5) | 0.066 (5) | 0.065 (5) | −0.018 (4) | −0.033 (4) | 0.001 (4) |
C4 | 0.051 (3) | 0.049 (4) | 0.055 (4) | −0.013 (3) | −0.016 (3) | −0.006 (3) |
C5 | 0.043 (3) | 0.061 (5) | 0.086 (6) | −0.018 (3) | −0.010 (3) | −0.011 (4) |
C6 | 0.056 (4) | 0.068 (5) | 0.089 (7) | −0.028 (4) | 0.016 (4) | −0.018 (4) |
C7 | 0.076 (5) | 0.070 (5) | 0.047 (4) | −0.025 (4) | 0.011 (4) | −0.010 (4) |
C8 | 0.055 (4) | 0.055 (4) | 0.052 (4) | −0.020 (3) | −0.003 (3) | −0.007 (3) |
C9 | 0.043 (3) | 0.035 (3) | 0.046 (4) | −0.007 (2) | −0.008 (2) | −0.006 (3) |
C10 | 0.040 (3) | 0.057 (4) | 0.054 (4) | −0.014 (3) | −0.015 (3) | 0.003 (3) |
C11 | 0.057 (4) | 0.050 (4) | 0.072 (5) | −0.014 (3) | −0.020 (3) | −0.010 (4) |
C12 | 0.074 (5) | 0.068 (5) | 0.108 (8) | −0.022 (4) | −0.030 (5) | −0.016 (5) |
C13 | 0.055 (4) | 0.048 (4) | 0.071 (5) | −0.013 (3) | −0.011 (3) | 0.006 (3) |
C14 | 0.066 (5) | 0.068 (5) | 0.087 (6) | −0.023 (4) | −0.028 (4) | −0.018 (5) |
C15 | 0.055 (4) | 0.082 (6) | 0.058 (5) | −0.017 (4) | −0.013 (3) | −0.021 (4) |
C16 | 0.036 (3) | 0.076 (5) | 0.045 (4) | −0.013 (3) | −0.004 (2) | −0.006 (3) |
C17 | 0.042 (3) | 0.103 (7) | 0.052 (5) | −0.014 (4) | −0.011 (3) | 0.019 (4) |
C18 | 0.056 (4) | 0.064 (5) | 0.076 (6) | −0.010 (4) | −0.008 (4) | 0.025 (4) |
C19 | 0.053 (4) | 0.053 (4) | 0.094 (7) | −0.017 (3) | −0.001 (4) | 0.003 (4) |
C20 | 0.047 (3) | 0.055 (4) | 0.060 (4) | −0.014 (3) | −0.006 (3) | −0.011 (3) |
C21 | 0.032 (3) | 0.049 (3) | 0.039 (3) | −0.014 (2) | −0.003 (2) | −0.001 (3) |
C22 | 0.063 (4) | 0.084 (5) | 0.032 (3) | −0.024 (4) | −0.014 (3) | 0.001 (3) |
C23 | 0.058 (4) | 0.085 (6) | 0.062 (5) | −0.016 (4) | −0.020 (3) | −0.001 (4) |
C24 | 0.078 (6) | 0.161 (11) | 0.074 (7) | −0.018 (6) | −0.040 (5) | 0.003 (7) |
I1—Cu1 | 2.5213 (14) | C11—H11B | 0.9700 |
I2—Cu1 | 2.5529 (12) | C12—H12A | 0.9600 |
I3—Cu1 | 2.5161 (13) | C12—H12B | 0.9600 |
N2—C13 | 1.331 (9) | C12—H12C | 0.9600 |
N2—C21 | 1.385 (8) | C13—C14 | 1.396 (11) |
N2—C22 | 1.474 (8) | C13—H13 | 0.9300 |
N1—C1 | 1.306 (9) | C14—C15 | 1.330 (12) |
N1—C9 | 1.382 (8) | C14—H14 | 0.9300 |
N1—C10 | 1.487 (7) | C15—C16 | 1.411 (10) |
C1—C2 | 1.373 (10) | C15—H15 | 0.9300 |
C1—H1 | 0.9300 | C16—C21 | 1.413 (9) |
C2—C3 | 1.362 (11) | C16—C17 | 1.414 (11) |
C2—H2 | 0.9300 | C17—C18 | 1.358 (12) |
C3—C4 | 1.390 (11) | C17—H17 | 0.9300 |
C3—H3 | 0.9300 | C18—C19 | 1.381 (12) |
C4—C9 | 1.414 (8) | C18—H18 | 0.9300 |
C4—C5 | 1.418 (10) | C19—C20 | 1.351 (11) |
C5—C6 | 1.333 (13) | C19—H19 | 0.9300 |
C5—H5 | 0.9300 | C20—C21 | 1.416 (9) |
C6—C7 | 1.400 (12) | C20—H20 | 0.9300 |
C6—H6 | 0.9300 | C22—C23 | 1.527 (10) |
C7—C8 | 1.370 (10) | C22—H22A | 0.9700 |
C7—H7 | 0.9300 | C22—H22B | 0.9700 |
C8—C9 | 1.407 (9) | C23—C24 | 1.496 (11) |
C8—H8 | 0.9300 | C23—H23A | 0.9700 |
C10—C11 | 1.518 (9) | C23—H23B | 0.9700 |
C10—H10A | 0.9700 | C24—H24A | 0.9600 |
C10—H10B | 0.9700 | C24—H24B | 0.9600 |
C11—C12 | 1.506 (10) | C24—H24C | 0.9600 |
C11—H11A | 0.9700 | ||
I3—Cu1—I1 | 124.29 (5) | H12A—C12—H12B | 109.5 |
I3—Cu1—I2 | 117.02 (5) | C11—C12—H12C | 109.5 |
I1—Cu1—I2 | 118.69 (4) | H12A—C12—H12C | 109.5 |
C13—N2—C21 | 121.1 (6) | H12B—C12—H12C | 109.5 |
C13—N2—C22 | 118.3 (6) | N2—C13—C14 | 121.5 (7) |
C21—N2—C22 | 120.6 (6) | N2—C13—H13 | 119.3 |
C1—N1—C9 | 121.8 (5) | C14—C13—H13 | 119.3 |
C1—N1—C10 | 117.8 (5) | C15—C14—C13 | 119.6 (7) |
C9—N1—C10 | 120.4 (5) | C15—C14—H14 | 120.2 |
N1—C1—C2 | 121.9 (6) | C13—C14—H14 | 120.2 |
N1—C1—H1 | 119.1 | C14—C15—C16 | 120.8 (7) |
C2—C1—H1 | 119.1 | C14—C15—H15 | 119.6 |
C3—C2—C1 | 119.3 (7) | C16—C15—H15 | 119.6 |
C3—C2—H2 | 120.3 | C15—C16—C21 | 118.9 (7) |
C1—C2—H2 | 120.3 | C15—C16—C17 | 122.8 (7) |
C2—C3—C4 | 120.3 (6) | C21—C16—C17 | 118.3 (7) |
C2—C3—H3 | 119.9 | C18—C17—C16 | 120.4 (7) |
C4—C3—H3 | 119.9 | C18—C17—H17 | 119.8 |
C3—C4—C9 | 118.8 (6) | C16—C17—H17 | 119.8 |
C3—C4—C5 | 123.6 (6) | C17—C18—C19 | 120.1 (7) |
C9—C4—C5 | 117.6 (7) | C17—C18—H18 | 120.0 |
C6—C5—C4 | 121.5 (7) | C19—C18—H18 | 120.0 |
C6—C5—H5 | 119.2 | C20—C19—C18 | 122.8 (8) |
C4—C5—H5 | 119.2 | C20—C19—H19 | 118.6 |
C5—C6—C7 | 120.3 (7) | C18—C19—H19 | 118.6 |
C5—C6—H6 | 119.8 | C19—C20—C21 | 118.3 (7) |
C7—C6—H6 | 119.8 | C19—C20—H20 | 120.8 |
C8—C7—C6 | 121.2 (8) | C21—C20—H20 | 120.8 |
C8—C7—H7 | 119.4 | N2—C21—C16 | 118.2 (6) |
C6—C7—H7 | 119.4 | N2—C21—C20 | 121.8 (6) |
C7—C8—C9 | 118.8 (7) | C16—C21—C20 | 120.1 (6) |
C7—C8—H8 | 120.6 | N2—C22—C23 | 111.4 (6) |
C9—C8—H8 | 120.6 | N2—C22—H22A | 109.3 |
N1—C9—C8 | 121.6 (5) | C23—C22—H22A | 109.3 |
N1—C9—C4 | 117.9 (6) | N2—C22—H22B | 109.3 |
C8—C9—C4 | 120.5 (6) | C23—C22—H22B | 109.3 |
N1—C10—C11 | 112.3 (5) | H22A—C22—H22B | 108.0 |
N1—C10—H10A | 109.2 | C24—C23—C22 | 110.2 (7) |
C11—C10—H10A | 109.2 | C24—C23—H23A | 109.6 |
N1—C10—H10B | 109.2 | C22—C23—H23A | 109.6 |
C11—C10—H10B | 109.2 | C24—C23—H23B | 109.6 |
H10A—C10—H10B | 107.9 | C22—C23—H23B | 109.6 |
C12—C11—C10 | 110.6 (6) | H23A—C23—H23B | 108.1 |
C12—C11—H11A | 109.5 | C23—C24—H24A | 109.5 |
C10—C11—H11A | 109.5 | C23—C24—H24B | 109.5 |
C12—C11—H11B | 109.5 | H24A—C24—H24B | 109.5 |
C10—C11—H11B | 109.5 | C23—C24—H24C | 109.5 |
H11A—C11—H11B | 108.1 | H24A—C24—H24C | 109.5 |
C11—C12—H12A | 109.5 | H24B—C24—H24C | 109.5 |
C11—C12—H12B | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10A···I2i | 0.97 | 3.09 | 4.046 (6) | 167 |
C13—H13···I3ii | 0.93 | 3.04 | 3.871 (6) | 150 |
C18—H18···I1iii | 0.93 | 3.08 | 3.986 (6) | 165 |
C2—H2···I3iv | 0.93 | 3.16 | 3.852 (6) | 133 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y, −z+1; (iii) x−1, y+1, z; (iv) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | (C12H14N)2[CuI3] |
Mr | 788.73 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.4373 (19), 9.5500 (19), 16.175 (3) |
α, β, γ (°) | 81.27 (3), 76.03 (3), 72.82 (3) |
V (Å3) | 1346.4 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 4.26 |
Crystal size (mm) | 0.20 × 0.18 × 0.16 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID Imaging Plate |
Absorption correction | Multi-scan (TEXRAY; Molecular Structure Corporation, 1999) |
Tmin, Tmax | 0.443, 0.506 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12812, 6176, 4121 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.149, 0.87 |
No. of reflections | 6176 |
No. of parameters | 273 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.69, −1.16 |
Computer programs: TEXRAY (Molecular Structure Corporation, 1999), TEXSAN (Molecular Structure Corporation, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEX (McArdle, 1995).
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10A···I2i | 0.97 | 3.09 | 4.046 (6) | 167.0 |
C13—H13···I3ii | 0.93 | 3.04 | 3.871 (6) | 150.0 |
C18—H18···I1iii | 0.93 | 3.08 | 3.986 (6) | 165.4 |
C2—H2···I3iv | 0.93 | 3.16 | 3.852 (6) | 133.0 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y, −z+1; (iii) x−1, y+1, z; (iv) x+1, y, z. |
In the title compound, (I) Fig. 1, the asymmetric unit contains two N-propylquinolinium cations which lie on opposite sides of the CuI32- anion. In the anion cluster, Cu—I bond distances lie in the range from 2.5161 (13) Å to 2.5529 (12)Å and the I1—Cu—I2, I2—Cu—I3 and I1—Cu—I3 bond angles are 124.29°, 117.02° and 118.69°, respectively. All of the atoms in the anion are essentially coplanar with an rms deviation from the [CuI3]2- mean plane of 0.0001|%A. The inorganic and organic components are linked via C—H···I hydrogen bonds to give a 3-dimensional network, Table 1. The cations are further aggregated through π-π stacking interactions with centroid to centroid distances of 3.48 (7)Å and 3.43 (5)Å respectively between the quinolinium rings, Fig 2.