Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010601910X/gd3021sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010601910X/gd3021Isup2.hkl |
CCDC reference: 616273
Crystals of the title compound were obtained by the direct reaction of pure powdered antimony with phthalonitrile (Kubiak & Janczak, 1993) under a stream of iodine vapour at 533 K.
All H atoms were positioned geometrically (C—H = 0.93 Å) and treated as riding, with Uiso(H) values of 1.2Ueq(C). The structure contains voids of 187 and 84 Å3 at (0, 1/2, 1/2) and (1/2, 0, 1/2), respectively. Since the crystals were obtained directly from phthalonitrile and powdered antimony under iodine vapour, no solvents are expected. This is confirmed by the experimental and X-ray densities.
Data collection: KM-4 CCD Software (Kuma, 2002); cell refinement: KM-4 CCD Software; data reduction: KM-4 CCD Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990b); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[Sb(C32H16N8)]4[Sb6I22] | Z = 1 |
Mr = 6059.42 | F(000) = 2732 |
Triclinic, P1 | Dx = 2.564 Mg m−3 Dm = 2.56 Mg m−3 Dm measured by flotation |
Hall symbol: -P 1 | Melting point: decomposition K |
a = 14.708 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 15.633 (3) Å | Cell parameters from 3544 reflections |
c = 19.158 (4) Å | θ = 3.4–28.3° |
α = 94.99 (3)° | µ = 6.08 mm−1 |
β = 96.62 (3)° | T = 295 K |
γ = 114.88 (3)° | Parallelepiped, black–violet |
V = 3924.4 (18) Å3 | 0.23 × 0.15 × 0.12 mm |
Kuma KM-4 diffractometer with CCD detector | 19326 independent reflections |
Radiation source: fine-focus sealed tube | 10908 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 1024x1024 with blocks 2x2 pixels mm-1 | θmax = 28.3°, θmin = 3.4° |
ω scan | h = −19→19 |
Absorption correction: analytical face-indexed (SHELXTL; Sheldrick, 1990b) | k = −20→18 |
Tmin = 0.334, Tmax = 0.527 | l = −25→25 |
34137 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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.074 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0181P)2] where P = (Fo2 + 2Fc2)/3 |
19326 reflections | (Δ/σ)max = 0.001 |
865 parameters | Δρmax = 1.65 e Å−3 |
0 restraints | Δρmin = −1.15 e Å−3 |
[Sb(C32H16N8)]4[Sb6I22] | γ = 114.88 (3)° |
Mr = 6059.42 | V = 3924.4 (18) Å3 |
Triclinic, P1 | Z = 1 |
a = 14.708 (3) Å | Mo Kα radiation |
b = 15.633 (3) Å | µ = 6.08 mm−1 |
c = 19.158 (4) Å | T = 295 K |
α = 94.99 (3)° | 0.23 × 0.15 × 0.12 mm |
β = 96.62 (3)° |
Kuma KM-4 diffractometer with CCD detector | 19326 independent reflections |
Absorption correction: analytical face-indexed (SHELXTL; Sheldrick, 1990b) | 10908 reflections with I > 2σ(I) |
Tmin = 0.334, Tmax = 0.527 | Rint = 0.035 |
34137 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.074 | H-atom parameters constrained |
S = 1.02 | Δρmax = 1.65 e Å−3 |
19326 reflections | Δρmin = −1.15 e Å−3 |
865 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 | ||
I1 | −0.04565 (3) | 0.09385 (3) | 0.06919 (2) | 0.03287 (11) | |
I2 | −0.21207 (3) | −0.02925 (3) | −0.14465 (2) | 0.04029 (11) | |
I3 | 0.23179 (3) | 0.22663 (3) | −0.02387 (2) | 0.03870 (12) | |
I4 | −0.02419 (4) | 0.26525 (3) | −0.09759 (3) | 0.05507 (14) | |
I5 | 0.07303 (3) | 0.09047 (3) | −0.22415 (2) | 0.04839 (12) | |
I6 | 0.13066 (3) | 0.23325 (3) | 0.27861 (2) | 0.05026 (13) | |
I7 | 0.40122 (3) | 0.33513 (3) | 0.18066 (2) | 0.05394 (14) | |
I8 | 0.15376 (4) | 0.39939 (4) | 0.12507 (3) | 0.06570 (16) | |
Sb1 | 0.01045 (3) | 0.10398 (3) | −0.08832 (2) | 0.03463 (11) | |
Sb2 | 0.18666 (3) | 0.23963 (3) | 0.13822 (2) | 0.04002 (12) | |
Sb3 | −0.16400 (3) | −0.03402 (3) | −0.31235 (2) | 0.06231 (12) | |
I9 | −0.17451 (4) | 0.13752 (4) | −0.31927 (3) | 0.06824 (17) | |
I10 | −0.09206 (5) | −0.04845 (5) | −0.43757 (3) | 0.0854 (2) | |
I11 | −0.37124 (4) | −0.13887 (4) | −0.36682 (4) | 0.08041 (19) | |
Sb4 | 0.31567 (3) | 0.03451 (3) | −0.02077 (3) | 0.04263 (12) | |
N1 | 0.4260 (4) | 0.0295 (4) | 0.0639 (3) | 0.0468 (15) | |
N2 | 0.3446 (5) | −0.1376 (4) | 0.0753 (4) | 0.0592 (17) | |
N3 | 0.2979 (4) | −0.1122 (4) | −0.0440 (3) | 0.0488 (15) | |
N4 | 0.2169 (4) | −0.1491 (4) | −0.1683 (3) | 0.0537 (16) | |
N5 | 0.3192 (4) | 0.0225 (4) | −0.1343 (3) | 0.0469 (15) | |
N6 | 0.4106 (4) | 0.1900 (4) | −0.1458 (3) | 0.0486 (15) | |
N7 | 0.4522 (4) | 0.1637 (4) | −0.0276 (3) | 0.0426 (14) | |
N8 | 0.5325 (4) | 0.2016 (4) | 0.0982 (3) | 0.0480 (15) | |
C1 | 0.4909 (5) | 0.1102 (5) | 0.1099 (4) | 0.0481 (18) | |
C2 | 0.5145 (5) | 0.0850 (5) | 0.1773 (4) | 0.0484 (19) | |
C3 | 0.5724 (5) | 0.1406 (6) | 0.2433 (4) | 0.061 (2) | |
H3 | 0.6079 | 0.2065 | 0.2470 | 0.073* | |
C4 | 0.5754 (6) | 0.0962 (6) | 0.3014 (4) | 0.066 (2) | |
H4 | 0.6136 | 0.1303 | 0.3452 | 0.079* | |
C5 | 0.5182 (7) | −0.0030 (7) | 0.2919 (5) | 0.077 (3) | |
H5 | 0.5208 | −0.0327 | 0.3316 | 0.093* | |
C6 | 0.4610 (6) | −0.0590 (6) | 0.2327 (5) | 0.068 (3) | |
H6 | 0.4247 | −0.1246 | 0.2306 | 0.081* | |
C7 | 0.4583 (5) | −0.0130 (5) | 0.1729 (4) | 0.0457 (18) | |
C8 | 0.4047 (5) | −0.0467 (5) | 0.1014 (4) | 0.0498 (19) | |
C9 | 0.2969 (5) | −0.1668 (5) | 0.0095 (5) | 0.0490 (19) | |
C10 | 0.2358 (6) | −0.2652 (5) | −0.0192 (5) | 0.060 (2) | |
C11 | 0.2042 (6) | −0.3508 (6) | 0.0088 (5) | 0.068 (2) | |
H11 | 0.2281 | −0.3501 | 0.0560 | 0.081* | |
C12 | 0.1404 (7) | −0.4334 (6) | −0.0311 (6) | 0.085 (3) | |
H12 | 0.1212 | −0.4894 | −0.0112 | 0.102* | |
C13 | 0.1028 (7) | −0.4377 (6) | −0.1001 (6) | 0.086 (3) | |
H13 | 0.0577 | −0.4968 | −0.1256 | 0.103* | |
C14 | 0.1294 (6) | −0.3547 (6) | −0.1361 (5) | 0.079 (3) | |
H14 | 0.1050 | −0.3565 | −0.1834 | 0.094* | |
C15 | 0.1962 (6) | −0.2720 (6) | −0.0906 (5) | 0.063 (2) | |
C16 | 0.2364 (6) | −0.1717 (5) | −0.1053 (5) | 0.057 (2) | |
C17 | 0.2579 (5) | −0.0600 (6) | −0.1824 (4) | 0.054 (2) | |
C18 | 0.2468 (6) | −0.0327 (6) | −0.2508 (5) | 0.060 (2) | |
C19 | 0.1922 (6) | −0.0861 (6) | −0.3164 (5) | 0.077 (3) | |
H19 | 0.1516 | −0.1514 | −0.3209 | 0.092* | |
C20 | 0.2005 (7) | −0.0387 (8) | −0.3743 (5) | 0.081 (3) | |
H20 | 0.1659 | −0.0728 | −0.4189 | 0.098* | |
C21 | 0.2587 (7) | 0.0577 (8) | −0.3676 (5) | 0.081 (3) | |
H21 | 0.2620 | 0.0876 | −0.4078 | 0.097* | |
C22 | 0.3131 (6) | 0.1123 (6) | −0.3024 (4) | 0.070 (2) | |
H22 | 0.3536 | 0.1776 | −0.2983 | 0.084* | |
C23 | 0.3039 (6) | 0.0658 (5) | −0.2454 (4) | 0.057 (2) | |
C24 | 0.3507 (5) | 0.1002 (5) | −0.1702 (4) | 0.0465 (18) | |
C25 | 0.4560 (5) | 0.2190 (5) | −0.0797 (4) | 0.0418 (17) | |
C26 | 0.5206 (5) | 0.3180 (5) | −0.0506 (3) | 0.0451 (18) | |
C27 | 0.5483 (5) | 0.4027 (5) | −0.0813 (4) | 0.055 (2) | |
H27 | 0.5283 | 0.4014 | −0.1294 | 0.066* | |
C28 | 0.6062 (5) | 0.4867 (5) | −0.0364 (4) | 0.061 (2) | |
H28 | 0.6216 | 0.5439 | −0.0541 | 0.074* | |
C29 | 0.6423 (6) | 0.4896 (6) | 0.0339 (5) | 0.071 (2) | |
H29 | 0.6837 | 0.5483 | 0.0616 | 0.086* | |
C30 | 0.6180 (5) | 0.4059 (5) | 0.0644 (4) | 0.0525 (19) | |
H30 | 0.6409 | 0.4069 | 0.1119 | 0.063* | |
C31 | 0.5566 (5) | 0.3204 (5) | 0.0181 (4) | 0.057 (2) | |
C32 | 0.5127 (5) | 0.2244 (5) | 0.0341 (4) | 0.0469 (18) | |
Sb5 | 0.39332 (3) | 0.38147 (3) | 0.36588 (2) | 0.04219 (12) | |
N11 | 0.5009 (4) | 0.3797 (4) | 0.4557 (3) | 0.0481 (15) | |
N12 | 0.6457 (4) | 0.4174 (4) | 0.3945 (3) | 0.0517 (16) | |
N13 | 0.5400 (4) | 0.4901 (4) | 0.3476 (3) | 0.0433 (14) | |
N14 | 0.4843 (5) | 0.5864 (4) | 0.2793 (3) | 0.0519 (16) | |
N15 | 0.3567 (4) | 0.5004 (4) | 0.3497 (3) | 0.0513 (16) | |
N16 | 0.2059 (4) | 0.4536 (4) | 0.4056 (3) | 0.0519 (16) | |
N17 | 0.3182 (4) | 0.3884 (4) | 0.4555 (3) | 0.0493 (15) | |
N18 | 0.3819 (5) | 0.3044 (4) | 0.5344 (3) | 0.0473 (15) | |
C33 | 0.4668 (6) | 0.3254 (5) | 0.5089 (3) | 0.0476 (19) | |
C34 | 0.5391 (5) | 0.2895 (5) | 0.5316 (4) | 0.0460 (18) | |
C35 | 0.5416 (6) | 0.2318 (6) | 0.5808 (4) | 0.070 (3) | |
H35 | 0.4923 | 0.2124 | 0.6099 | 0.085* | |
C36 | 0.6196 (6) | 0.2024 (6) | 0.5868 (4) | 0.071 (2) | |
H36 | 0.6215 | 0.1626 | 0.6198 | 0.085* | |
C37 | 0.6969 (7) | 0.2331 (6) | 0.5425 (5) | 0.079 (3) | |
H37 | 0.7468 | 0.2111 | 0.5451 | 0.094* | |
C38 | 0.6957 (6) | 0.2958 (6) | 0.4961 (4) | 0.070 (2) | |
H38 | 0.7472 | 0.3202 | 0.4693 | 0.083* | |
C39 | 0.6160 (5) | 0.3214 (5) | 0.4905 (4) | 0.056 (2) | |
C40 | 0.5895 (6) | 0.3788 (5) | 0.4436 (4) | 0.0494 (19) | |
C41 | 0.6228 (5) | 0.4728 (5) | 0.3515 (4) | 0.0497 (19) | |
C42 | 0.6893 (6) | 0.5235 (5) | 0.3043 (4) | 0.0515 (19) | |
C43 | 0.7766 (6) | 0.5263 (5) | 0.2891 (4) | 0.069 (2) | |
H43 | 0.8069 | 0.4917 | 0.3109 | 0.083* | |
C44 | 0.8214 (6) | 0.5847 (6) | 0.2377 (5) | 0.075 (3) | |
H44 | 0.8821 | 0.5880 | 0.2255 | 0.090* | |
C45 | 0.7770 (6) | 0.6357 (6) | 0.2062 (4) | 0.066 (2) | |
H45 | 0.8071 | 0.6719 | 0.1720 | 0.079* | |
C46 | 0.6894 (6) | 0.6348 (5) | 0.2238 (4) | 0.061 (2) | |
H46 | 0.6615 | 0.6728 | 0.2045 | 0.074* | |
C47 | 0.6419 (6) | 0.5731 (5) | 0.2732 (4) | 0.0516 (19) | |
C48 | 0.5499 (6) | 0.5541 (5) | 0.3001 (4) | 0.0457 (18) | |
C49 | 0.3972 (6) | 0.5643 (5) | 0.3016 (4) | 0.0482 (19) | |
C50 | 0.3239 (5) | 0.5979 (5) | 0.2783 (4) | 0.0506 (19) | |
C51 | 0.3250 (6) | 0.6598 (5) | 0.2300 (4) | 0.056 (2) | |
H51 | 0.3798 | 0.6872 | 0.2064 | 0.067* | |
C52 | 0.2422 (7) | 0.6787 (6) | 0.2186 (4) | 0.066 (2) | |
H52 | 0.2412 | 0.7208 | 0.1874 | 0.079* | |
C53 | 0.1584 (7) | 0.6359 (5) | 0.2532 (4) | 0.068 (2) | |
H53 | 0.1024 | 0.6487 | 0.2429 | 0.081* | |
C54 | 0.1566 (6) | 0.5760 (5) | 0.3016 (4) | 0.060 (2) | |
H54 | 0.1017 | 0.5489 | 0.3252 | 0.072* | |
C55 | 0.2423 (6) | 0.5577 (5) | 0.3134 (4) | 0.0527 (19) | |
C56 | 0.2654 (6) | 0.4984 (5) | 0.3606 (4) | 0.052 (2) | |
C57 | 0.2331 (6) | 0.4039 (5) | 0.4487 (4) | 0.0493 (19) | |
C58 | 0.1674 (6) | 0.3561 (5) | 0.5025 (4) | 0.060 (2) | |
C59 | 0.0786 (6) | 0.3495 (6) | 0.5150 (5) | 0.072 (2) | |
H59 | 0.0455 | 0.3792 | 0.4895 | 0.087* | |
C60 | 0.0363 (7) | 0.2973 (7) | 0.5668 (5) | 0.079 (3) | |
H60 | −0.0264 | 0.2912 | 0.5768 | 0.106* | |
C61 | 0.0879 (6) | 0.2537 (6) | 0.6043 (4) | 0.068 (2) | |
H61 | 0.0585 | 0.2177 | 0.6388 | 0.082* | |
C62 | 0.1828 (6) | 0.2630 (5) | 0.5909 (4) | 0.063 (2) | |
H62 | 0.2177 | 0.2351 | 0.6168 | 0.076* | |
C63 | 0.2230 (6) | 0.3144 (5) | 0.5388 (4) | 0.0506 (19) | |
C64 | 0.3111 (6) | 0.3359 (5) | 0.5102 (4) | 0.0478 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0357 (2) | 0.0348 (3) | 0.0346 (3) | 0.0119 (2) | 0.0051 (2) | 0.0061 (2) |
I2 | 0.0347 (2) | 0.0455 (3) | 0.0362 (3) | 0.0127 (2) | 0.0070 (2) | 0.0084 (2) |
I3 | 0.0338 (2) | 0.0344 (3) | 0.0415 (3) | 0.0126 (2) | 0.0059 (2) | 0.0057 (2) |
I4 | 0.0649 (3) | 0.0437 (3) | 0.0626 (3) | 0.0293 (3) | 0.0074 (3) | 0.0125 (3) |
I5 | 0.0451 (3) | 0.0560 (3) | 0.0389 (3) | 0.0154 (2) | 0.0131 (2) | 0.0075 (2) |
I6 | 0.0552 (3) | 0.0491 (3) | 0.0420 (3) | 0.0175 (2) | 0.0110 (2) | 0.0081 (2) |
I7 | 0.0414 (3) | 0.0594 (3) | 0.0419 (3) | 0.0054 (2) | 0.0024 (2) | 0.0049 (3) |
I8 | 0.0860 (4) | 0.0485 (3) | 0.0694 (4) | 0.0342 (3) | 0.0144 (3) | 0.0150 (3) |
Sb1 | 0.0353 (2) | 0.0311 (2) | 0.0337 (2) | 0.0119 (2) | 0.0051 (2) | 0.0062 (2) |
Sb2 | 0.0386 (3) | 0.0361 (3) | 0.0377 (3) | 0.0107 (2) | 0.0045 (2) | 0.0056 (2) |
Sb3 | 0.0706 (3) | 0.0584 (3) | 0.0533 (3) | 0.0145 (2) | 0.0069 (2) | 0.0078 (2) |
I9 | 0.0755 (4) | 0.0486 (3) | 0.0806 (4) | 0.0276 (3) | 0.0031 (3) | 0.0201 (3) |
I10 | 0.1028 (5) | 0.1039 (5) | 0.0438 (3) | 0.0356 (4) | 0.0293 (3) | 0.0098 (3) |
I11 | 0.0544 (3) | 0.0552 (3) | 0.1079 (5) | 0.0127 (3) | −0.0126 (3) | −0.0141 (3) |
Sb4 | 0.0386 (3) | 0.0360 (3) | 0.0554 (3) | 0.0142 (2) | 0.0191 (2) | 0.0128 (2) |
N1 | 0.035 (3) | 0.042 (4) | 0.068 (4) | 0.016 (3) | 0.019 (3) | 0.024 (3) |
N2 | 0.053 (4) | 0.045 (4) | 0.082 (5) | 0.021 (3) | 0.016 (4) | 0.020 (4) |
N3 | 0.048 (4) | 0.039 (4) | 0.065 (4) | 0.020 (3) | 0.024 (3) | 0.006 (3) |
N4 | 0.063 (4) | 0.044 (4) | 0.056 (4) | 0.021 (3) | 0.027 (3) | 0.003 (3) |
N5 | 0.043 (3) | 0.038 (3) | 0.056 (4) | 0.012 (3) | 0.020 (3) | 0.001 (3) |
N6 | 0.050 (4) | 0.049 (4) | 0.053 (4) | 0.023 (3) | 0.022 (3) | 0.016 (3) |
N7 | 0.037 (3) | 0.041 (3) | 0.052 (4) | 0.012 (3) | 0.025 (3) | 0.017 (3) |
N8 | 0.041 (3) | 0.058 (4) | 0.045 (4) | 0.017 (3) | 0.013 (3) | 0.021 (3) |
C1 | 0.044 (4) | 0.048 (5) | 0.058 (5) | 0.022 (4) | 0.013 (4) | 0.016 (4) |
C2 | 0.035 (4) | 0.046 (5) | 0.072 (6) | 0.020 (4) | 0.020 (4) | 0.025 (4) |
C3 | 0.053 (5) | 0.065 (5) | 0.068 (6) | 0.027 (4) | 0.008 (4) | 0.024 (5) |
C4 | 0.070 (6) | 0.081 (7) | 0.048 (5) | 0.033 (5) | 0.012 (4) | 0.020 (5) |
C5 | 0.063 (6) | 0.094 (7) | 0.094 (8) | 0.042 (6) | 0.021 (5) | 0.057 (7) |
C6 | 0.045 (5) | 0.050 (5) | 0.096 (7) | 0.008 (4) | 0.001 (5) | 0.040 (5) |
C7 | 0.032 (4) | 0.052 (5) | 0.067 (5) | 0.028 (4) | 0.018 (4) | 0.016 (4) |
C8 | 0.039 (4) | 0.044 (5) | 0.079 (6) | 0.024 (4) | 0.027 (4) | 0.019 (5) |
C9 | 0.040 (4) | 0.037 (4) | 0.075 (6) | 0.016 (4) | 0.023 (4) | 0.019 (4) |
C10 | 0.055 (5) | 0.045 (5) | 0.090 (7) | 0.032 (4) | 0.019 (5) | 0.001 (5) |
C11 | 0.074 (6) | 0.053 (5) | 0.089 (7) | 0.031 (5) | 0.042 (5) | 0.023 (5) |
C12 | 0.106 (8) | 0.037 (5) | 0.114 (9) | 0.040 (5) | 0.008 (7) | −0.011 (6) |
C13 | 0.093 (7) | 0.039 (5) | 0.103 (8) | 0.011 (5) | 0.020 (7) | −0.009 (6) |
C14 | 0.088 (7) | 0.046 (5) | 0.082 (7) | 0.013 (5) | 0.014 (5) | −0.008 (5) |
C15 | 0.055 (5) | 0.050 (5) | 0.085 (7) | 0.017 (4) | 0.037 (5) | 0.012 (5) |
C16 | 0.050 (5) | 0.042 (5) | 0.094 (7) | 0.025 (4) | 0.039 (5) | 0.014 (5) |
C17 | 0.051 (5) | 0.051 (5) | 0.059 (5) | 0.022 (4) | 0.012 (4) | 0.001 (4) |
C18 | 0.057 (5) | 0.064 (6) | 0.061 (6) | 0.030 (4) | 0.012 (4) | 0.002 (5) |
C19 | 0.076 (6) | 0.065 (6) | 0.076 (7) | 0.024 (5) | 0.008 (6) | −0.008 (6) |
C20 | 0.097 (8) | 0.090 (8) | 0.055 (6) | 0.050 (7) | −0.006 (5) | −0.020 (6) |
C21 | 0.103 (8) | 0.094 (8) | 0.051 (6) | 0.051 (6) | 0.002 (5) | 0.012 (6) |
C22 | 0.078 (6) | 0.075 (6) | 0.057 (6) | 0.029 (5) | 0.021 (5) | 0.024 (5) |
C23 | 0.057 (5) | 0.052 (5) | 0.058 (5) | 0.015 (4) | 0.024 (4) | 0.015 (4) |
C24 | 0.047 (4) | 0.036 (4) | 0.052 (5) | 0.012 (4) | 0.017 (4) | 0.006 (4) |
C25 | 0.038 (4) | 0.039 (4) | 0.050 (5) | 0.015 (3) | 0.016 (4) | 0.012 (4) |
C26 | 0.042 (4) | 0.048 (4) | 0.034 (4) | 0.005 (3) | 0.012 (3) | 0.016 (4) |
C27 | 0.059 (5) | 0.050 (5) | 0.056 (5) | 0.021 (4) | 0.015 (4) | 0.015 (4) |
C28 | 0.060 (5) | 0.037 (4) | 0.066 (6) | 0.004 (4) | −0.003 (4) | 0.007 (4) |
C29 | 0.071 (6) | 0.051 (5) | 0.068 (6) | 0.005 (4) | 0.010 (5) | 0.004 (5) |
C30 | 0.052 (5) | 0.043 (4) | 0.053 (5) | 0.009 (4) | 0.014 (4) | 0.012 (4) |
C31 | 0.049 (5) | 0.053 (5) | 0.053 (5) | 0.005 (4) | 0.013 (4) | 0.017 (4) |
C32 | 0.028 (4) | 0.041 (4) | 0.068 (6) | 0.010 (3) | 0.013 (4) | 0.011 (4) |
Sb5 | 0.0506 (3) | 0.0329 (3) | 0.0344 (3) | 0.0102 (2) | 0.0031 (2) | 0.0089 (2) |
N11 | 0.053 (4) | 0.032 (3) | 0.046 (4) | 0.006 (3) | 0.001 (3) | 0.016 (3) |
N12 | 0.053 (4) | 0.047 (4) | 0.046 (4) | 0.013 (3) | 0.009 (3) | 0.011 (3) |
N13 | 0.045 (3) | 0.033 (3) | 0.040 (3) | 0.002 (3) | 0.013 (3) | 0.015 (3) |
N14 | 0.061 (4) | 0.041 (4) | 0.039 (4) | 0.009 (3) | 0.005 (3) | 0.007 (3) |
N15 | 0.056 (4) | 0.043 (4) | 0.048 (4) | 0.011 (3) | 0.017 (3) | 0.019 (3) |
N16 | 0.067 (4) | 0.041 (4) | 0.046 (4) | 0.019 (3) | 0.017 (3) | 0.010 (3) |
N17 | 0.051 (4) | 0.040 (3) | 0.052 (4) | 0.015 (3) | 0.006 (3) | 0.009 (3) |
N18 | 0.063 (4) | 0.040 (3) | 0.030 (3) | 0.014 (3) | 0.006 (3) | 0.005 (3) |
C33 | 0.067 (5) | 0.034 (4) | 0.020 (4) | 0.008 (4) | −0.008 (4) | −0.003 (3) |
C34 | 0.046 (4) | 0.043 (4) | 0.037 (4) | 0.012 (4) | −0.007 (3) | 0.005 (4) |
C35 | 0.060 (5) | 0.093 (7) | 0.041 (5) | 0.014 (5) | 0.003 (4) | 0.032 (5) |
C36 | 0.070 (6) | 0.087 (6) | 0.069 (6) | 0.043 (5) | 0.009 (5) | 0.041 (5) |
C37 | 0.090 (7) | 0.078 (6) | 0.078 (6) | 0.046 (5) | 0.004 (5) | 0.030 (5) |
C38 | 0.058 (5) | 0.090 (7) | 0.060 (6) | 0.028 (5) | 0.009 (4) | 0.033 (5) |
C39 | 0.042 (4) | 0.053 (5) | 0.052 (5) | 0.007 (4) | −0.013 (4) | 0.009 (4) |
C40 | 0.045 (5) | 0.045 (5) | 0.042 (5) | 0.009 (4) | −0.010 (4) | 0.006 (4) |
C41 | 0.049 (5) | 0.039 (4) | 0.050 (5) | 0.012 (4) | −0.002 (4) | 0.009 (4) |
C42 | 0.047 (5) | 0.041 (4) | 0.056 (5) | 0.009 (4) | 0.007 (4) | 0.014 (4) |
C43 | 0.057 (5) | 0.060 (5) | 0.079 (6) | 0.011 (4) | 0.004 (5) | 0.033 (5) |
C44 | 0.052 (5) | 0.076 (6) | 0.069 (6) | 0.003 (5) | 0.013 (5) | 0.006 (5) |
C45 | 0.075 (6) | 0.073 (6) | 0.060 (6) | 0.032 (5) | 0.039 (5) | 0.026 (5) |
C46 | 0.064 (5) | 0.056 (5) | 0.040 (5) | 0.002 (4) | 0.008 (4) | 0.015 (4) |
C47 | 0.052 (5) | 0.039 (4) | 0.044 (5) | 0.004 (4) | 0.000 (4) | 0.005 (4) |
C48 | 0.050 (5) | 0.031 (4) | 0.036 (4) | 0.003 (3) | −0.006 (4) | −0.001 (3) |
C49 | 0.064 (5) | 0.033 (4) | 0.044 (5) | 0.018 (4) | 0.004 (4) | 0.013 (4) |
C50 | 0.056 (5) | 0.055 (5) | 0.046 (5) | 0.028 (4) | 0.009 (4) | 0.020 (4) |
C51 | 0.078 (6) | 0.045 (5) | 0.043 (5) | 0.026 (4) | 0.009 (4) | 0.008 (4) |
C52 | 0.092 (7) | 0.058 (5) | 0.059 (5) | 0.042 (5) | 0.009 (5) | 0.024 (5) |
C53 | 0.086 (6) | 0.051 (5) | 0.076 (6) | 0.040 (5) | 0.000 (5) | 0.018 (5) |
C54 | 0.065 (5) | 0.042 (5) | 0.074 (6) | 0.027 (4) | −0.002 (4) | 0.004 (4) |
C55 | 0.058 (5) | 0.049 (5) | 0.045 (5) | 0.018 (4) | 0.003 (4) | 0.008 (4) |
C56 | 0.064 (5) | 0.029 (4) | 0.063 (5) | 0.018 (4) | 0.011 (4) | 0.011 (4) |
C57 | 0.060 (5) | 0.041 (4) | 0.042 (4) | 0.018 (4) | 0.008 (4) | 0.007 (4) |
C58 | 0.067 (6) | 0.047 (5) | 0.053 (5) | 0.009 (4) | 0.022 (4) | 0.008 (4) |
C59 | 0.069 (6) | 0.084 (6) | 0.077 (6) | 0.038 (5) | 0.027 (5) | 0.039 (5) |
C60 | 0.077 (7) | 0.093 (8) | 0.068 (6) | 0.038 (6) | 0.032 (5) | 0.030 (6) |
C61 | 0.062 (6) | 0.087 (6) | 0.057 (5) | 0.027 (5) | 0.026 (4) | 0.029 (5) |
C62 | 0.082 (6) | 0.049 (5) | 0.048 (5) | 0.018 (4) | 0.019 (5) | 0.004 (4) |
C63 | 0.079 (6) | 0.029 (4) | 0.041 (4) | 0.020 (4) | 0.011 (4) | 0.011 (4) |
C64 | 0.057 (5) | 0.042 (4) | 0.036 (4) | 0.013 (4) | 0.012 (4) | 0.004 (4) |
Sb1—I1 | 3.2186 (10) | C27—C28 | 1.373 (9) |
Sb1—I2 | 3.0451 (15) | C27—H27 | 0.9300 |
Sb1—I3 | 3.0344 (15) | C28—C29 | 1.379 (10) |
Sb1—I4 | 2.7903 (8) | C28—H28 | 0.9300 |
Sb1—I5 | 2.8781 (9) | C29—C30 | 1.403 (9) |
Sb1—I1i | 3.3864 (9) | C29—H29 | 0.9300 |
Sb2—I6 | 2.9001 (9) | C30—C31 | 1.408 (9) |
Sb2—I7 | 2.8428 (12) | C30—H30 | 0.9300 |
Sb2—I8 | 2.7630 (9) | C31—C32 | 1.440 (9) |
Sb2—I1 | 3.2402 (16) | Sb5—I6 | 3.6598 (18) |
Sb2—I3 | 3.2563 (10) | Sb5—I7 | 3.5843 (11) |
Sb2—I2i | 3.4734 (9) | Sb5—I11i | 3.6696 (10) |
Sb3—I2 | 3.3696 (10) | Sb5—N17 | 2.165 (6) |
Sb3—I5 | 3.3402 (9) | Sb5—N15 | 2.180 (6) |
Sb3—I6i | 3.4527 (10) | Sb5—N13 | 2.203 (5) |
Sb3—I9 | 2.7638 (9) | Sb5—N11 | 2.210 (5) |
Sb3—I10 | 2.7600 (10) | N11—C40 | 1.356 (8) |
Sb3—I11 | 2.7985 (14) | N11—C33 | 1.385 (8) |
Sb4—I3 | 3.6984 (10) | N12—C40 | 1.337 (8) |
Sb4—I1i | 3.5750 (15) | N12—C41 | 1.360 (8) |
Sb4—I2i | 3.6640 (11) | N13—C41 | 1.349 (8) |
Sb4—N5 | 2.175 (6) | N13—C48 | 1.385 (8) |
Sb4—N1 | 2.189 (5) | N14—C48 | 1.303 (8) |
Sb4—N3 | 2.195 (5) | N14—C49 | 1.312 (8) |
Sb4—N7 | 2.195 (5) | N15—C56 | 1.370 (9) |
N1—C1 | 1.369 (8) | N15—C49 | 1.410 (8) |
N1—C8 | 1.386 (8) | N16—C57 | 1.320 (8) |
N2—C9 | 1.310 (9) | N16—C56 | 1.326 (8) |
N2—C8 | 1.329 (8) | N17—C57 | 1.365 (8) |
N3—C16 | 1.386 (10) | N17—C64 | 1.374 (8) |
N3—C9 | 1.388 (9) | N18—C33 | 1.315 (8) |
N4—C16 | 1.320 (9) | N18—C64 | 1.379 (8) |
N4—C17 | 1.331 (9) | C33—C34 | 1.439 (9) |
N5—C24 | 1.382 (8) | C34—C35 | 1.369 (9) |
N5—C17 | 1.396 (8) | C34—C39 | 1.395 (9) |
N6—C25 | 1.306 (8) | C35—C36 | 1.401 (10) |
N6—C24 | 1.310 (8) | C35—H35 | 0.9300 |
N7—C25 | 1.368 (8) | C36—C37 | 1.441 (11) |
N7—C32 | 1.394 (8) | C36—H36 | 0.9300 |
N8—C32 | 1.342 (8) | C37—C38 | 1.385 (10) |
N8—C1 | 1.349 (8) | C37—H37 | 0.9300 |
C1—C2 | 1.430 (9) | C38—C39 | 1.385 (10) |
C2—C7 | 1.390 (9) | C38—H38 | 0.9300 |
C2—C3 | 1.421 (10) | C39—C40 | 1.456 (9) |
C3—C4 | 1.367 (9) | C41—C42 | 1.442 (9) |
C3—H3 | 0.9300 | C42—C43 | 1.334 (10) |
C4—C5 | 1.402 (11) | C42—C47 | 1.373 (9) |
C4—H4 | 0.9300 | C43—C44 | 1.427 (10) |
C5—C6 | 1.322 (11) | C43—H43 | 0.9300 |
C5—H5 | 0.9300 | C44—C45 | 1.363 (10) |
C6—C7 | 1.411 (10) | C44—H44 | 0.9300 |
C6—H6 | 0.9300 | C45—C46 | 1.365 (10) |
C7—C8 | 1.432 (10) | C45—H45 | 0.9300 |
C9—C10 | 1.433 (10) | C46—C47 | 1.434 (9) |
C10—C11 | 1.397 (10) | C46—H46 | 0.9300 |
C10—C15 | 1.401 (11) | C47—C48 | 1.426 (9) |
C11—C12 | 1.332 (10) | C49—C50 | 1.431 (9) |
C11—H11 | 0.9300 | C50—C55 | 1.382 (9) |
C12—C13 | 1.358 (12) | C50—C51 | 1.392 (9) |
C12—H12 | 0.9300 | C51—C52 | 1.369 (10) |
C13—C14 | 1.450 (11) | C51—H51 | 0.9300 |
C13—H13 | 0.9300 | C52—C53 | 1.406 (10) |
C14—C15 | 1.391 (10) | C52—H52 | 0.9300 |
C14—H14 | 0.9300 | C53—C54 | 1.368 (9) |
C15—C16 | 1.490 (10) | C53—H53 | 0.9300 |
C17—C18 | 1.426 (10) | C54—C55 | 1.405 (9) |
C18—C19 | 1.394 (10) | C54—H54 | 0.9300 |
C18—C23 | 1.397 (10) | C55—C56 | 1.462 (9) |
C19—C20 | 1.376 (11) | C57—C58 | 1.521 (10) |
C19—H19 | 0.9300 | C58—C59 | 1.319 (10) |
C20—C21 | 1.371 (11) | C58—C63 | 1.405 (10) |
C20—H20 | 0.9300 | C59—C60 | 1.376 (10) |
C21—C22 | 1.391 (11) | C59—H59 | 0.9300 |
C21—H21 | 0.9300 | C60—C61 | 1.398 (10) |
C22—C23 | 1.354 (10) | C60—H60 | 0.9300 |
C22—H22 | 0.9300 | C61—C62 | 1.398 (10) |
C23—C24 | 1.470 (10) | C61—H61 | 0.9300 |
C25—C26 | 1.449 (9) | C62—C63 | 1.366 (9) |
C26—C31 | 1.353 (9) | C62—H62 | 0.9300 |
C26—C27 | 1.414 (9) | C63—C64 | 1.387 (9) |
I4—Sb1—I5 | 98.07 (3) | C29—C30—C31 | 115.4 (7) |
I4—Sb1—I3 | 91.27 (3) | C29—C30—H30 | 122.3 |
I5—Sb1—I3 | 88.51 (4) | C31—C30—H30 | 122.3 |
I4—Sb1—I2 | 91.97 (3) | C26—C31—C30 | 122.9 (7) |
I5—Sb1—I2 | 93.97 (4) | C26—C31—C32 | 107.9 (7) |
I3—Sb1—I2 | 175.60 (4) | C30—C31—C32 | 128.8 (7) |
I4—Sb1—I1 | 91.13 (3) | N8—C32—N7 | 128.3 (6) |
I5—Sb1—I1 | 170.59 (2) | N8—C32—C31 | 123.3 (7) |
I3—Sb1—I1 | 89.31 (4) | N7—C32—C31 | 108.4 (6) |
I2—Sb1—I1 | 87.65 (4) | N17—Sb5—N15 | 78.4 (2) |
I8—Sb2—I7 | 97.48 (4) | N17—Sb5—N13 | 126.4 (2) |
I8—Sb2—I6 | 91.02 (3) | N15—Sb5—N13 | 78.5 (2) |
I7—Sb2—I6 | 98.05 (4) | N17—Sb5—N11 | 77.8 (2) |
I3—Sb2—I1 | 85.19 (4) | N15—Sb5—N11 | 125.5 (2) |
I10—Sb3—I9 | 98.51 (4) | N13—Sb5—N11 | 77.7 (2) |
I10—Sb3—I11 | 97.36 (4) | C40—N11—C33 | 108.6 (6) |
I9—Sb3—I11 | 92.18 (4) | C40—N11—Sb5 | 119.4 (5) |
I2—Sb3—I5 | 80.44 (4) | C33—N11—Sb5 | 121.2 (5) |
N5—Sb4—N1 | 127.4 (2) | C40—N12—C41 | 121.8 (6) |
N5—Sb4—N3 | 79.0 (2) | C41—N13—C48 | 107.4 (6) |
N1—Sb4—N3 | 77.5 (2) | C41—N13—Sb5 | 120.9 (4) |
N5—Sb4—N7 | 77.8 (2) | C48—N13—Sb5 | 124.3 (5) |
N1—Sb4—N7 | 78.7 (2) | C48—N14—C49 | 125.0 (6) |
N3—Sb4—N7 | 125.32 (19) | C56—N15—C49 | 109.1 (6) |
C1—N1—C8 | 107.1 (6) | C56—N15—Sb5 | 121.8 (4) |
C1—N1—Sb4 | 120.8 (4) | C49—N15—Sb5 | 124.0 (5) |
C8—N1—Sb4 | 123.0 (5) | C57—N16—C56 | 120.4 (6) |
C9—N2—C8 | 123.7 (7) | C57—N17—C64 | 105.8 (6) |
C16—N3—C9 | 109.0 (6) | C57—N17—Sb5 | 121.6 (5) |
C16—N3—Sb4 | 121.0 (5) | C64—N17—Sb5 | 125.2 (5) |
C9—N3—Sb4 | 121.6 (5) | C33—N18—C64 | 122.9 (6) |
C16—N4—C17 | 122.9 (7) | N18—C33—N11 | 128.2 (7) |
C24—N5—C17 | 109.4 (6) | N18—C33—C34 | 123.3 (6) |
C24—N5—Sb4 | 123.1 (5) | N11—C33—C34 | 108.4 (7) |
C17—N5—Sb4 | 123.5 (5) | C35—C34—C39 | 119.9 (7) |
C25—N6—C24 | 122.4 (6) | C35—C34—C33 | 132.5 (8) |
C25—N7—C32 | 107.3 (5) | C39—C34—C33 | 107.6 (6) |
C25—N7—Sb4 | 122.8 (4) | C34—C35—C36 | 119.0 (8) |
C32—N7—Sb4 | 120.1 (4) | C34—C35—H35 | 120.5 |
C32—N8—C1 | 120.8 (6) | C36—C35—H35 | 120.5 |
N8—C1—N1 | 129.2 (7) | C35—C36—C37 | 120.8 (7) |
N8—C1—C2 | 121.1 (7) | C35—C36—H36 | 119.6 |
N1—C1—C2 | 109.6 (6) | C37—C36—H36 | 119.6 |
C7—C2—C3 | 120.0 (7) | C38—C37—C36 | 118.9 (8) |
C7—C2—C1 | 107.2 (7) | C38—C37—H37 | 120.6 |
C3—C2—C1 | 132.4 (7) | C36—C37—H37 | 120.6 |
C4—C3—C2 | 119.3 (7) | C37—C38—C39 | 118.5 (8) |
C4—C3—H3 | 120.4 | C37—C38—H38 | 120.7 |
C2—C3—H3 | 120.4 | C39—C38—H38 | 120.7 |
C3—C4—C5 | 116.9 (8) | C38—C39—C34 | 122.8 (7) |
C3—C4—H4 | 121.5 | C38—C39—C40 | 131.4 (8) |
C5—C4—H4 | 121.5 | C34—C39—C40 | 105.8 (7) |
C6—C5—C4 | 127.2 (8) | N12—C40—N11 | 128.8 (6) |
C6—C5—H5 | 116.4 | N12—C40—C39 | 121.4 (7) |
C4—C5—H5 | 116.4 | N11—C40—C39 | 109.6 (7) |
C5—C6—C7 | 115.7 (7) | N13—C41—N12 | 126.7 (7) |
C5—C6—H6 | 122.1 | N13—C41—C42 | 111.3 (6) |
C7—C6—H6 | 122.1 | N12—C41—C42 | 122.0 (7) |
C2—C7—C6 | 120.8 (7) | C43—C42—C47 | 123.4 (7) |
C2—C7—C8 | 106.3 (7) | C43—C42—C41 | 132.5 (7) |
C6—C7—C8 | 132.8 (7) | C47—C42—C41 | 104.1 (7) |
N2—C8—N1 | 125.6 (7) | C42—C43—C44 | 117.0 (8) |
N2—C8—C7 | 124.8 (7) | C42—C43—H43 | 121.5 |
N1—C8—C7 | 109.6 (6) | C44—C43—H43 | 121.5 |
N2—C9—N3 | 128.0 (7) | C45—C44—C43 | 121.3 (8) |
N2—C9—C10 | 123.4 (7) | C45—C44—H44 | 119.4 |
N3—C9—C10 | 108.6 (7) | C43—C44—H44 | 119.4 |
C11—C10—C15 | 116.1 (8) | C44—C45—C46 | 121.4 (8) |
C11—C10—C9 | 134.8 (9) | C44—C45—H45 | 119.3 |
C15—C10—C9 | 109.0 (8) | C46—C45—H45 | 119.3 |
C12—C11—C10 | 121.2 (9) | C45—C46—C47 | 117.4 (8) |
C12—C11—H11 | 119.4 | C45—C46—H46 | 121.3 |
C10—C11—H11 | 119.4 | C47—C46—H46 | 121.3 |
C11—C12—C13 | 121.4 (9) | C42—C47—C48 | 109.6 (7) |
C11—C12—H12 | 119.3 | C42—C47—C46 | 119.4 (7) |
C13—C12—H12 | 119.3 | C48—C47—C46 | 130.9 (7) |
C12—C13—C14 | 123.4 (9) | N14—C48—N13 | 126.8 (7) |
C12—C13—H13 | 118.3 | N14—C48—C47 | 125.4 (7) |
C14—C13—H13 | 118.3 | N13—C48—C47 | 107.6 (6) |
C15—C14—C13 | 111.2 (8) | N14—C49—N15 | 126.8 (6) |
C15—C14—H14 | 124.4 | N14—C49—C50 | 125.5 (7) |
C13—C14—H14 | 124.4 | N15—C49—C50 | 107.6 (7) |
C14—C15—C10 | 126.7 (8) | C55—C50—C51 | 121.1 (7) |
C14—C15—C16 | 128.1 (9) | C55—C50—C49 | 108.0 (6) |
C10—C15—C16 | 105.1 (8) | C51—C50—C49 | 130.9 (7) |
N4—C16—N3 | 128.7 (7) | C52—C51—C50 | 117.3 (8) |
N4—C16—C15 | 123.0 (8) | C52—C51—H51 | 121.4 |
N3—C16—C15 | 108.2 (8) | C50—C51—H51 | 121.4 |
N4—C17—N5 | 127.1 (7) | C51—C52—C53 | 121.4 (7) |
N4—C17—C18 | 125.1 (7) | C51—C52—H52 | 119.3 |
N5—C17—C18 | 107.8 (7) | C53—C52—H52 | 119.3 |
C19—C18—C23 | 119.8 (8) | C54—C53—C52 | 122.1 (8) |
C19—C18—C17 | 131.4 (8) | C54—C53—H53 | 118.9 |
C23—C18—C17 | 108.7 (7) | C52—C53—H53 | 118.9 |
C20—C19—C18 | 117.5 (8) | C53—C54—C55 | 116.1 (8) |
C20—C19—H19 | 121.2 | C53—C54—H54 | 122.0 |
C18—C19—H19 | 121.2 | C55—C54—H54 | 122.0 |
C21—C20—C19 | 121.3 (9) | C50—C55—C54 | 122.0 (7) |
C21—C20—H20 | 119.4 | C50—C55—C56 | 107.5 (6) |
C19—C20—H20 | 119.4 | C54—C55—C56 | 130.4 (7) |
C20—C21—C22 | 122.0 (9) | N16—C56—N15 | 128.9 (7) |
C20—C21—H21 | 119.0 | N16—C56—C55 | 123.6 (7) |
C22—C21—H21 | 119.0 | N15—C56—C55 | 107.5 (7) |
C23—C22—C21 | 116.7 (8) | N16—C57—N17 | 129.6 (7) |
C23—C22—H22 | 121.7 | N16—C57—C58 | 120.6 (7) |
C21—C22—H22 | 121.7 | N17—C57—C58 | 109.7 (7) |
C22—C23—C18 | 122.6 (8) | C59—C58—C63 | 124.7 (8) |
C22—C23—C24 | 131.0 (7) | C59—C58—C57 | 131.9 (8) |
C18—C23—C24 | 106.3 (7) | C63—C58—C57 | 103.3 (7) |
N6—C24—N5 | 129.3 (7) | C58—C59—C60 | 118.0 (8) |
N6—C24—C23 | 123.0 (7) | C58—C59—H59 | 121.0 |
N5—C24—C23 | 107.7 (6) | C60—C59—H59 | 121.0 |
N6—C25—N7 | 127.1 (6) | C59—C60—C61 | 119.8 (8) |
N6—C25—C26 | 123.7 (6) | C59—C60—H60 | 120.1 |
N7—C25—C26 | 109.2 (6) | C61—C60—H60 | 120.1 |
C31—C26—C27 | 121.0 (7) | C60—C61—C62 | 121.2 (8) |
C31—C26—C25 | 107.2 (6) | C60—C61—H61 | 119.4 |
C27—C26—C25 | 131.9 (7) | C62—C61—H61 | 119.4 |
C28—C27—C26 | 116.5 (7) | C63—C62—C61 | 118.1 (8) |
C28—C27—H27 | 121.7 | C63—C62—H62 | 121.0 |
C26—C27—H27 | 121.7 | C61—C62—H62 | 121.0 |
C27—C28—C29 | 122.5 (7) | C62—C63—C64 | 134.0 (8) |
C27—C28—H28 | 118.7 | C62—C63—C58 | 118.3 (8) |
C29—C28—H28 | 118.7 | C64—C63—C58 | 107.8 (7) |
C28—C29—C30 | 121.4 (7) | N17—C64—N18 | 124.7 (7) |
C28—C29—H29 | 119.3 | N17—C64—C63 | 113.4 (7) |
C30—C29—H29 | 119.3 | N18—C64—C63 | 121.9 (7) |
Symmetry code: (i) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Sb(C32H16N8)]4[Sb6I22] |
Mr | 6059.42 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 14.708 (3), 15.633 (3), 19.158 (4) |
α, β, γ (°) | 94.99 (3), 96.62 (3), 114.88 (3) |
V (Å3) | 3924.4 (18) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 6.08 |
Crystal size (mm) | 0.23 × 0.15 × 0.12 |
Data collection | |
Diffractometer | Kuma KM-4 diffractometer with CCD detector |
Absorption correction | Analytical face-indexed (SHELXTL; Sheldrick, 1990b) |
Tmin, Tmax | 0.334, 0.527 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 34137, 19326, 10908 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.074, 1.02 |
No. of reflections | 19326 |
No. of parameters | 865 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.65, −1.15 |
Computer programs: KM-4 CCD Software (Kuma, 2002), KM-4 CCD Software, SHELXS97 (Sheldrick, 1990a), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1990b).
Sb1—I1 | 3.2186 (10) | Sb3—I10 | 2.7600 (10) |
Sb1—I2 | 3.0451 (15) | Sb3—I11 | 2.7985 (14) |
Sb1—I3 | 3.0344 (15) | Sb4—I3 | 3.6984 (10) |
Sb1—I4 | 2.7903 (8) | Sb4—I1i | 3.5750 (15) |
Sb1—I5 | 2.8781 (9) | Sb4—I2i | 3.6640 (11) |
Sb1—I1i | 3.3864 (9) | Sb4—N5 | 2.175 (6) |
Sb2—I6 | 2.9001 (9) | Sb4—N1 | 2.189 (5) |
Sb2—I7 | 2.8428 (12) | Sb4—N3 | 2.195 (5) |
Sb2—I8 | 2.7630 (9) | Sb4—N7 | 2.195 (5) |
Sb2—I1 | 3.2402 (16) | Sb5—I6 | 3.6598 (18) |
Sb2—I3 | 3.2563 (10) | Sb5—I7 | 3.5843 (11) |
Sb2—I2i | 3.4734 (9) | Sb5—I11i | 3.6696 (10) |
Sb3—I2 | 3.3696 (10) | Sb5—N17 | 2.165 (6) |
Sb3—I5 | 3.3402 (9) | Sb5—N15 | 2.180 (6) |
Sb3—I6i | 3.4527 (10) | Sb5—N13 | 2.203 (5) |
Sb3—I9 | 2.7638 (9) | Sb5—N11 | 2.210 (5) |
I4—Sb1—I5 | 98.07 (3) | N5—Sb4—N3 | 79.0 (2) |
I5—Sb1—I2 | 93.97 (4) | N1—Sb4—N3 | 77.5 (2) |
I3—Sb1—I1 | 89.31 (4) | N5—Sb4—N7 | 77.8 (2) |
I8—Sb2—I7 | 97.48 (4) | N1—Sb4—N7 | 78.7 (2) |
I7—Sb2—I6 | 98.05 (4) | N17—Sb5—N15 | 78.4 (2) |
I3—Sb2—I1 | 85.19 (4) | N15—Sb5—N13 | 78.5 (2) |
I10—Sb3—I9 | 98.51 (4) | N17—Sb5—N11 | 77.8 (2) |
I10—Sb3—I11 | 97.36 (4) | N13—Sb5—N11 | 77.7 (2) |
I2—Sb3—I5 | 80.44 (4) |
Symmetry code: (i) −x, −y, −z. |
The present study is a continuation of our investigations on the synthesis, characterization and stereochemistry of metallophthalocyaninate complexes, which have been obtained under oxidation conditions of iodine vapour (Janczak, 2003,
and references cited therein). Although metallophthalocyaninate complexes have been known for a long time, metallophthathalocyaninate complexes with the metals of periodic group 15 have rarely been investigated. The title SbIII–phthalocyanine–iodine complex, (I), is an example of a complex containing the same metal ion in both the cation and the anion, i.e. in [SbPc]+ as well as in the [Sb6I22]4− counter-ion. A search of the Cambridge Structural Database (Version 5.24; Allen, 2002) for phthalocyaninate structures containing the same metal in both cation and anion yields only two isostructural complexes, viz. [(SbPc)4(Sb4I16)] (Janczak & Idemori, 2002) and [(BiPc)4(Bi4I16)] (Kubiak & Ejsmont, 1999), two non-isostructural comlexes, viz. [(AsPc)2(As4I14)] (Janczak & Kubiak, 2003) and [(SbPc)2(Sb4I14)] (Perpétuo & Janczak, 2005), and [(AsPc)2(As2I8)] (Janczak & Perpétuo, 2006), none of which contains an [M6I22]4− ion. Thus the present [(Sb4Pc)(Sb6I22)] structure is the first example of this type of phthalocyanine system that has been structurally characterized.
The crystal structure of (I) is built up of separate but interacting [SbPc]+ and [Sb6I22]4− units (Fig. 1). The two crystallographically independent [SbPc]+ cations have essentially the same geometry. In both [SbPc]+ cations, the phthalocyaninate(2-) macrocycle shows a saucer shaped form, as a result of the interaction of the central SbIII ion with the I atoms of the [Sb6I22]4− counter-ion (Fig. 2). The greatest deviations from the mean planes defined by the four isoindole N atoms of the Pc macrocycles are observed for the outermost C atoms of the phenyl rings C18–C23 [0.224–0.574 (1) Å] and C34–C39 [0.049–0.426 (1) Å] for the [Sb4Pc]+ and [Sb5Pc]+ cations, respectively. The positively charged Sb4 and Sb5 atoms of the [SbPc]+ cations are significantly displaced from the N4 isoindole planes toward the I atoms of the [Sb6I22]4− counter-ion, the displacements being almost equal, viz. 0.984 (1) and 0.989 (1) Å, respectively. The influence of the ionic attraction between the oppositely charged [SbPc]+ and [Sb6I22]4− ions is clearly manifested in the Sb—Nisoindole coordination, leading to the molecular symmetry of the Sb—N core being close to Cs rather than the C4v symmetry that corresponds to the conformation in solution.
The anionic part of (I) consists of six deformed SbI6 octahedra joined together by bridging I atoms into a centrosymmetric [Sb6I22]4− ion (Fig. 1b). Generally, the Sb—I bond lengths fall into two groups, namely shorter Sb—I bonds with terminal I atoms and longer Sb—I bonds involving the bridging I atoms. However, in the [Sb6I22]4− anion, two different bridging I atoms exist. Atoms I1 and I2 bridge three Sb atoms, while atoms I3, I5 and I6 bridge only two Sb atoms. The distortion of the SbI6 polyhedron from Oh symmetry is likely to be due to the electron lone pair on the SbIII ion. Looking in more detail at the differences between the Sb—I bond lengths, as well as in the coordination geometry around atoms Sb1, Sb2 and Sb3, it is clear that they are coordindated to the I atoms through forces of different strength. Atom Sb1 links two I atoms with relatively short Sb—I bonds, two I atoms with intermediate Sb—I values and two I atoms with relatively long Sb—I bonds, the longest being the Sb1—I1i bond (Table 1). In the coordination environments of atoms Sb2 and Sb3, three short Sb—I bonds and three relatively long Sb—I bonds are observed. Thus the [Sb6I22]4− ion can be regarded as being composed of three symmetrically equivalent pairs of units, viz. one [SbI5]2− and two crystallographically independent [SbI3]− units. Atom Sb1 in the [SbI5]2− unit has distorted square-pyramidal coordination, formed by four I atoms in the basal plane and one apical I atom with a relatively short Sb—I bond. The relatively long Sb1—I1i bond in a position trans to the apical I atom indicates the stereochemical effect of the electron lone pair (Gillespie, 1992). In the coordination environments of atoms Sb2 and Sb3, it is not clear in which direction the electron lone pair points, since the three relatively long Sb—I bonds are very similar. However, the mutual orientation of the [SbI5]2− and two [SbI3]− units related by an inversion centre leads to the formation of an [Sb6I22]4− counter-ion, in which all Sb atoms have a distorted octahedral coordination environment. A similar pattern concerning the Sb—I bond lengths is also observed in the [Sb4I16]4− (Janczak & Idemori, 2002) and [Sb4I14]2− (Perpétuo & Janczak, 2005) counter-ions of two antimony(III)–phthalocyanine complexes. In the first complex, the [Sb4I16]4− ion consists of four distorted SbI6 octahedra, while in the second, the [Sb4I14]2− ion consists of two pairs of deformed SbI6 octahedra and distorted square-pyramidal SbI5 polyhedra.
In the unit cell (Fig. 2), there seems to be significant ionic attraction between the [SbPc]+ cations and [Sb6I22]4− counter-ions. The basic packing unit includes two pairs of [SbPc]+ macrocycles associated by an inversion centre and a [Sb6I22]4− counter-ion, thus each anion is surrounded by four [SbPc]+ cations. Atoms Sb4 and Sb5 of two crystallographically independent [SbPc]+ cations each interact with three I atoms of the [Sb6I22]4− counter-ion (Sb4 with I1, I2 and I3, and Sb5 with I6, I7 and I11), since the Sb—I contacts are considerable shorter than the sum of the van der Waals radii of Sb and I of 4.35 Å (Shannon, 1976). The centrosymmetric [(SbPc)4(Sb6I22)] aggregates in the crystal structure form stacks along [111], with π–π interactions between adjacent back-to-back-oriented pairs of Pc macrocycles. The interplanar N4-isoindole–N4-isondole distance within the stack is ~3.4 Å. The value indicates a strong π–π interaction and overlapping of the π clouds of the phthalocyanine macrocycle, since this distance is comparable to the van der Waals distance of 3.4 Å for aromatic C atoms (Pauling, 1960). Strong π–π interaction is a common feature in the structures of phthalocyanine and its metal complexes, and determines their crystal architectures. The π–π interactions also play an important role in association of metallophthalocyanines in solution (Nevin et al., 1987; Terekhov et al., 1996; Isago et al., 1997, 1998).
Although the crystal structure of (I) is built up from oppositely charged [SbPc]+ and [Sb6I22]4− species, the compound does not possess the characteristic properties of ionic crystals. The solubility of this compound in polar solvents, such as water, methanol and ethanol, is insignificant, and it is only slightly soluble in pyridine, dimethylformamide, dimethyl sulfoxide, chloronaphthalene, quinoline and diazabicycloundecane. As can be seen from the crystal structure architecture (Fig. 2), both hydrophilic parts of this complex are surrounded by the hydrophobic peripheral phenyl rings of the Pc macrocycle.
The electronic spectrum of this salt in pyridine solution exhibits two bands characteristic of the (phthalocyaninate)2− macrocycle, viz. at 680 nm (Q-band) and at 350 nm (B-band) (Stillman & Nyokong, 1989). The electrical conductivity of (I), measured on a single-crystal along the stacking direction of [(SbPc)4(Sb6I22)] aggregates (along the [111] direction), exhibits non-metallic character (dσ/dT > 0). At room temperature, the conductivity is ~1.7–2.2 × 10−7 Ω−1 cm−1.