In the ionic charge-transfer (CT) complex composed of bis(ethylenedithio)tetrathiafulvalene (ET) and 2,3-dichloro-5,6-dicyano-
p-benzoquinone (DDQ), C
10H
8S
8·C
8Cl
2N
2O
2, the donor and acceptor molecules both form centrosymmetric dimers associated by strong face-to-face
-
interactions. The disordered DDQ molecules form a one-dimensional
-stacked column, while the ET molecules form a two-leg ladder through additional short S
S contacts between adjacent
-
-bonded dimers. The crystal structure of ET-DDQ revealed in this study will provide a valuable example of the two-leg spin ladder system, which has rarely been reported for ET-based CT complexes.
Supporting information
CCDC reference: 934612
Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: VESTA (Momma et al., 2008) and ORTEP-3 (Farrugia, 2012).
Bi[5,6-dihydro-1,3-dithiolo[4,5-b][1,4]-dithiine-2-ylidene]–2,3-dichloro-5,6-dicyano-
p-benzoquinone (1/1)
top
Crystal data top
C8Cl2N2O2·C10H8S8 | Z = 2 |
Mr = 611.64 | F(000) = 616 |
Triclinic, P1 | Dx = 1.879 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71075 Å |
a = 6.5975 (6) Å | Cell parameters from 7626 reflections |
b = 13.0254 (10) Å | θ = 3.2–27.5° |
c = 13.3531 (10) Å | µ = 1.10 mm−1 |
α = 103.739 (2)° | T = 296 K |
β = 98.123 (3)° | Plate, dark brown |
γ = 99.217 (2)° | 0.70 × 0.10 × 0.10 mm |
V = 1080.85 (15) Å3 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 4903 independent reflections |
Radiation source: fine-focus sealed tube | 3513 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
Detector resolution: 10.000 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −16→16 |
Tmin = 0.461, Tmax = 0.896 | l = −17→16 |
10126 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.071 | H-atom parameters constrained |
wR(F2) = 0.188 | w = 1/[σ2(Fo2) + (0.0542P)2 + 4.3292P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max < 0.001 |
4903 reflections | Δρmax = 0.92 e Å−3 |
335 parameters | Δρmin = −0.58 e Å−3 |
34 restraints | |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 1.0460 (9) | 0.3624 (4) | 0.4322 (4) | 0.0298 (11) | |
C2 | 0.9891 (8) | 0.4227 (4) | 0.3642 (4) | 0.0294 (11) | |
C3 | 1.0442 (9) | 0.2325 (4) | 0.5499 (4) | 0.0296 (11) | |
C4 | 1.2485 (9) | 0.2737 (4) | 0.5547 (4) | 0.0296 (11) | |
C5 | 0.7843 (9) | 0.4982 (4) | 0.2297 (4) | 0.0300 (11) | |
C6 | 0.9911 (9) | 0.5384 (4) | 0.2329 (4) | 0.0291 (11) | |
C7 | 1.1521 (11) | 0.0798 (5) | 0.6536 (5) | 0.0439 (15) | |
H7A | 1.1974 | 0.1072 | 0.7290 | 0.053* | |
H7B | 1.0999 | 0.0028 | 0.6386 | 0.053* | |
C8 | 1.3406 (10) | 0.0971 (5) | 0.6031 (5) | 0.0412 (14) | |
H8A | 1.2999 | 0.0641 | 0.5281 | 0.049* | |
H8B | 1.4446 | 0.0610 | 0.6306 | 0.049* | |
C9 | 0.6908 (10) | 0.6457 (5) | 0.1293 (6) | 0.0442 (15) | |
H9A | 0.5880 | 0.6686 | 0.0846 | 0.053* | |
H9B | 0.7287 | 0.7001 | 0.1962 | 0.053* | |
C10 | 0.8798 (11) | 0.6413 (6) | 0.0808 (5) | 0.0469 (16) | |
H10A | 0.9183 | 0.7082 | 0.0617 | 0.056* | |
H10B | 0.8445 | 0.5832 | 0.0166 | 0.056* | |
S1 | 0.8629 (2) | 0.27615 (12) | 0.47025 (11) | 0.0334 (3) | |
S2 | 1.3016 (2) | 0.36480 (12) | 0.48178 (12) | 0.0346 (3) | |
S3 | 0.7316 (2) | 0.41712 (12) | 0.31239 (12) | 0.0340 (3) | |
S4 | 1.1691 (2) | 0.50624 (12) | 0.32397 (11) | 0.0310 (3) | |
S5 | 0.9370 (3) | 0.14136 (15) | 0.61439 (15) | 0.0468 (4) | |
S6 | 1.4570 (2) | 0.23847 (13) | 0.62507 (12) | 0.0366 (4) | |
S7 | 0.5708 (2) | 0.51923 (14) | 0.15089 (14) | 0.0431 (4) | |
S8 | 1.1028 (3) | 0.62121 (15) | 0.16244 (14) | 0.0460 (4) | |
C11a | 0.8006 (13) | −0.0432 (5) | 0.0309 (5) | 0.0243 (15) | 0.789 (6) |
C12a | 0.7769 (12) | 0.0680 (6) | 0.0653 (5) | 0.0235 (14) | 0.789 (6) |
C13a | 0.7309 (11) | 0.1291 (6) | 0.0006 (5) | 0.0245 (14) | 0.789 (6) |
C14a | 0.6999 (11) | 0.0875 (5) | −0.1146 (5) | 0.0251 (14) | 0.789 (6) |
C15a | 0.7140 (11) | −0.0240 (6) | −0.1516 (5) | 0.0242 (14) | 0.789 (6) |
C16a | 0.7608 (13) | −0.0867 (6) | −0.0832 (5) | 0.0247 (15) | 0.789 (6) |
C17a | 0.6819 (13) | −0.0682 (7) | −0.2627 (6) | 0.0352 (17) | 0.789 (6) |
C18a | 0.7576 (12) | −0.1987 (8) | −0.1225 (6) | 0.0339 (17) | 0.789 (6) |
O1a | 0.8518 (14) | −0.0978 (5) | 0.0911 (4) | 0.0308 (16) | 0.789 (6) |
O2a | 0.6519 (10) | 0.1442 (5) | −0.1745 (4) | 0.0402 (14) | 0.789 (6) |
N1a | 0.6541 (14) | −0.1009 (7) | −0.3511 (7) | 0.054 (2) | 0.789 (6) |
N2a | 0.754 (2) | −0.2887 (9) | −0.1565 (11) | 0.061 (4) | 0.789 (6) |
Cl1a | 0.8040 (4) | 0.11901 (19) | 0.20017 (15) | 0.0361 (6) | 0.789 (6) |
Cl2a | 0.7062 (3) | 0.26067 (18) | 0.04500 (16) | 0.0391 (6) | 0.789 (6) |
C11b | 0.792 (7) | −0.0735 (18) | 0.0035 (16) | 0.031 (2)* | 0.211 (6) |
C12b | 0.759 (6) | −0.1197 (18) | −0.1095 (16) | 0.031 (2)* | 0.211 (6) |
C13b | 0.723 (5) | −0.0622 (16) | −0.1799 (14) | 0.031 (2)* | 0.211 (6) |
C14b | 0.702 (6) | 0.0500 (16) | −0.1460 (15) | 0.031 (2)* | 0.211 (6) |
C15b | 0.741 (5) | 0.0996 (17) | −0.0358 (15) | 0.031 (2)* | 0.211 (6) |
C16b | 0.789 (7) | 0.0415 (19) | 0.0378 (16) | 0.031 (2)* | 0.211 (6) |
C17b | 0.723 (4) | 0.2089 (16) | −0.001 (2) | 0.031 (2)* | 0.211 (6) |
C18b | 0.812 (4) | 0.091 (2) | 0.1469 (17) | 0.031 (2)* | 0.211 (6) |
O1b | 0.843 (7) | −0.123 (2) | 0.070 (2) | 0.031 (2)* | 0.211 (6) |
O2b | 0.673 (4) | 0.1069 (17) | −0.2083 (16) | 0.031 (2)* | 0.211 (6) |
N1b | 0.710 (4) | 0.2959 (17) | 0.029 (2) | 0.031 (2)* | 0.211 (6) |
N2b | 0.818 (5) | 0.119 (3) | 0.2361 (18) | 0.031 (2)* | 0.211 (6) |
Cl1b | 0.762 (2) | −0.2567 (13) | −0.1516 (13) | 0.041 (3)* | 0.211 (6) |
Cl2b | 0.6696 (15) | −0.1221 (9) | −0.3127 (9) | 0.047 (3)* | 0.211 (6) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.030 (3) | 0.031 (3) | 0.028 (3) | 0.005 (2) | 0.005 (2) | 0.008 (2) |
C2 | 0.028 (3) | 0.030 (3) | 0.031 (3) | 0.005 (2) | 0.007 (2) | 0.009 (2) |
C3 | 0.033 (3) | 0.029 (3) | 0.029 (3) | 0.008 (2) | 0.006 (2) | 0.010 (2) |
C4 | 0.030 (3) | 0.031 (3) | 0.027 (3) | 0.008 (2) | 0.000 (2) | 0.009 (2) |
C5 | 0.033 (3) | 0.027 (3) | 0.028 (3) | 0.005 (2) | 0.001 (2) | 0.008 (2) |
C6 | 0.036 (3) | 0.025 (3) | 0.027 (3) | 0.010 (2) | 0.004 (2) | 0.008 (2) |
C7 | 0.060 (4) | 0.039 (3) | 0.041 (3) | 0.009 (3) | 0.010 (3) | 0.026 (3) |
C8 | 0.048 (4) | 0.035 (3) | 0.044 (3) | 0.015 (3) | 0.001 (3) | 0.018 (3) |
C9 | 0.044 (4) | 0.044 (4) | 0.051 (4) | 0.013 (3) | 0.001 (3) | 0.027 (3) |
C10 | 0.047 (4) | 0.059 (4) | 0.043 (4) | 0.017 (3) | 0.006 (3) | 0.028 (3) |
S1 | 0.0297 (7) | 0.0359 (8) | 0.0348 (7) | 0.0017 (6) | 0.0026 (6) | 0.0147 (6) |
S2 | 0.0298 (7) | 0.0395 (8) | 0.0401 (8) | 0.0062 (6) | 0.0059 (6) | 0.0218 (7) |
S3 | 0.0293 (7) | 0.0365 (8) | 0.0383 (8) | 0.0042 (6) | 0.0034 (6) | 0.0169 (7) |
S4 | 0.0273 (7) | 0.0355 (7) | 0.0344 (7) | 0.0078 (6) | 0.0054 (6) | 0.0165 (6) |
S5 | 0.0446 (9) | 0.0498 (10) | 0.0585 (10) | 0.0082 (7) | 0.0171 (8) | 0.0351 (9) |
S6 | 0.0347 (8) | 0.0390 (8) | 0.0365 (8) | 0.0062 (6) | 0.0004 (6) | 0.0151 (7) |
S7 | 0.0329 (8) | 0.0431 (9) | 0.0524 (10) | 0.0054 (7) | −0.0062 (7) | 0.0209 (8) |
S8 | 0.0357 (8) | 0.0589 (11) | 0.0547 (10) | 0.0086 (7) | 0.0070 (7) | 0.0383 (9) |
C11a | 0.019 (3) | 0.029 (4) | 0.024 (3) | 0.000 (3) | 0.000 (3) | 0.012 (3) |
C12a | 0.020 (3) | 0.030 (4) | 0.023 (4) | 0.004 (3) | 0.004 (3) | 0.011 (3) |
C13a | 0.023 (3) | 0.027 (4) | 0.024 (3) | 0.009 (3) | 0.003 (3) | 0.007 (3) |
C14a | 0.019 (3) | 0.029 (4) | 0.027 (4) | 0.005 (3) | 0.002 (3) | 0.009 (3) |
C15a | 0.025 (3) | 0.026 (4) | 0.020 (3) | 0.003 (3) | 0.003 (3) | 0.006 (3) |
C16a | 0.026 (3) | 0.026 (4) | 0.024 (4) | 0.009 (3) | 0.003 (3) | 0.009 (3) |
C17a | 0.045 (5) | 0.033 (4) | 0.032 (4) | 0.014 (3) | 0.007 (3) | 0.012 (4) |
C18a | 0.035 (4) | 0.036 (5) | 0.027 (4) | 0.004 (4) | −0.002 (3) | 0.007 (4) |
O1a | 0.034 (3) | 0.036 (4) | 0.025 (3) | 0.008 (3) | 0.006 (3) | 0.013 (3) |
O2a | 0.061 (4) | 0.039 (3) | 0.025 (3) | 0.016 (3) | 0.004 (3) | 0.015 (3) |
N1a | 0.081 (6) | 0.048 (5) | 0.039 (4) | 0.020 (4) | 0.011 (4) | 0.018 (4) |
N2a | 0.080 (8) | 0.038 (7) | 0.063 (6) | 0.011 (6) | 0.020 (5) | 0.009 (6) |
Cl1a | 0.0434 (11) | 0.0436 (11) | 0.0227 (11) | 0.0102 (8) | 0.0072 (9) | 0.0098 (10) |
Cl2a | 0.0489 (12) | 0.0318 (12) | 0.0397 (11) | 0.0159 (9) | 0.0087 (9) | 0.0098 (9) |
Geometric parameters (Å, º) top
C1—C2 | 1.386 (7) | C11a—O1a | 1.241 (7) |
C1—S2 | 1.715 (6) | C11a—C12a | 1.453 (9) |
C1—S1 | 1.729 (5) | C11a—C16a | 1.463 (9) |
C2—S4 | 1.711 (5) | C12a—C13a | 1.341 (9) |
C2—S3 | 1.725 (6) | C12a—Cl1a | 1.737 (7) |
C3—C4 | 1.356 (8) | C13a—C14a | 1.477 (9) |
C3—S1 | 1.741 (6) | C13a—Cl2a | 1.718 (7) |
C3—S5 | 1.743 (5) | C14a—O2a | 1.254 (7) |
C4—S2 | 1.729 (5) | C14a—C15a | 1.441 (9) |
C4—S6 | 1.740 (5) | C15a—C16a | 1.396 (9) |
C5—C6 | 1.371 (8) | C15a—C17a | 1.430 (10) |
C5—S3 | 1.733 (5) | C16a—C18a | 1.424 (12) |
C5—S7 | 1.734 (6) | C17a—N1a | 1.133 (11) |
C6—S8 | 1.737 (5) | C18a—N2a | 1.148 (15) |
C6—S4 | 1.740 (5) | C11b—O1b | 1.253 (17) |
C7—C8 | 1.507 (9) | C11b—C12b | 1.456 (18) |
C7—S5 | 1.813 (7) | C11b—C16b | 1.462 (18) |
C7—H7A | 0.9700 | C12b—C13b | 1.352 (18) |
C7—H7B | 0.9700 | C12b—Cl1B | 1.742 (17) |
C8—S6 | 1.815 (6) | C13b—C14b | 1.460 (17) |
C8—H8A | 0.9700 | C13b—Cl2B | 1.720 (17) |
C8—H8B | 0.9700 | C14b—O2b | 1.255 (17) |
C9—C10 | 1.488 (9) | C14b—C15b | 1.427 (17) |
C9—S7 | 1.815 (6) | C15b—C16b | 1.408 (18) |
C9—H9A | 0.9700 | C15b—C17b | 1.419 (18) |
C9—H9B | 0.9700 | C16b—C18b | 1.422 (19) |
C10—S8 | 1.796 (7) | C17b—N1b | 1.129 (19) |
C10—H10A | 0.9700 | C18b—N2b | 1.15 (2) |
C10—H10B | 0.9700 | | |
| | | |
C2—C1—S2 | 122.7 (4) | C2—S4—C6 | 96.2 (3) |
C2—C1—S1 | 122.1 (4) | C3—S5—C7 | 104.1 (3) |
S2—C1—S1 | 115.2 (3) | C4—S6—C8 | 97.3 (3) |
C1—C2—S4 | 122.5 (4) | C5—S7—C9 | 98.5 (3) |
C1—C2—S3 | 122.3 (4) | C6—S8—C10 | 103.0 (3) |
S4—C2—S3 | 115.3 (3) | O1a—C11a—C12a | 124.2 (6) |
C4—C3—S1 | 116.5 (4) | O1a—C11a—C16a | 121.8 (6) |
C4—C3—S5 | 128.4 (4) | C12a—C11a—C16a | 114.0 (5) |
S1—C3—S5 | 115.1 (3) | C13a—C12a—C11a | 124.5 (6) |
C3—C4—S2 | 116.6 (4) | C13a—C12a—Cl1a | 120.3 (5) |
C3—C4—S6 | 124.7 (4) | C11a—C12a—Cl1a | 115.2 (5) |
S2—C4—S6 | 118.6 (3) | C12a—C13a—C14a | 122.0 (6) |
C6—C5—S3 | 116.4 (4) | C12a—C13a—Cl2a | 122.8 (5) |
C6—C5—S7 | 126.9 (4) | C14a—C13a—Cl2a | 115.2 (5) |
S3—C5—S7 | 116.7 (3) | O2a—C14a—C15a | 123.4 (6) |
C5—C6—S8 | 129.5 (4) | O2a—C14a—C13a | 121.5 (6) |
C5—C6—S4 | 115.9 (4) | C15a—C14a—C13a | 115.0 (5) |
S8—C6—S4 | 114.6 (3) | C16a—C15a—C17a | 120.8 (6) |
C8—C7—S5 | 116.7 (4) | C16a—C15a—C14a | 122.3 (6) |
C8—C7—H7A | 108.1 | C17a—C15a—C14a | 116.9 (6) |
S5—C7—H7A | 108.1 | C15a—C16a—C18a | 120.7 (6) |
C8—C7—H7B | 108.1 | C15a—C16a—C11a | 122.2 (6) |
S5—C7—H7B | 108.1 | C18a—C16a—C11a | 117.0 (6) |
H7A—C7—H7B | 107.3 | N1a—C17a—C15a | 178.1 (9) |
C7—C8—S6 | 113.2 (5) | N2a—C18a—C16a | 178.4 (9) |
C7—C8—H8A | 108.9 | O1b—C11b—C12b | 123.6 (19) |
S6—C8—H8A | 108.9 | O1b—C11b—C16b | 120.1 (19) |
C7—C8—H8B | 108.9 | C12b—C11b—C16b | 115.8 (16) |
S6—C8—H8B | 108.9 | C13b—C12b—C11b | 123.1 (16) |
H8A—C8—H8B | 107.8 | C13b—C12b—Cl1B | 120.6 (15) |
C10—C9—S7 | 114.7 (5) | C11b—C12b—Cl1B | 116.3 (14) |
C10—C9—H9A | 108.6 | C12b—C13b—C14b | 121.0 (16) |
S7—C9—H9A | 108.6 | C12b—C13b—Cl2B | 121.5 (14) |
C10—C9—H9B | 108.6 | C14b—C13b—Cl2B | 117.0 (13) |
S7—C9—H9B | 108.6 | O2b—C14b—C15b | 119.0 (17) |
H9A—C9—H9B | 107.6 | O2b—C14b—C13b | 123.2 (17) |
C9—C10—S8 | 114.9 (5) | C15b—C14b—C13b | 117.5 (15) |
C9—C10—H10A | 108.5 | C16b—C15b—C17b | 120.1 (17) |
S8—C10—H10A | 108.5 | C16b—C15b—C14b | 121.5 (16) |
C9—C10—H10B | 108.5 | C17b—C15b—C14b | 118.3 (17) |
S8—C10—H10B | 108.5 | C15b—C16b—C18b | 120.0 (18) |
H10A—C10—H10B | 107.5 | C15b—C16b—C11b | 120.7 (16) |
C1—S1—C3 | 95.5 (3) | C18b—C16b—C11b | 118.8 (17) |
C1—S2—C4 | 96.2 (3) | N1b—C17b—C15b | 178 (3) |
C2—S3—C5 | 96.0 (3) | N2b—C18b—C16b | 172 (3) |
| | | |
S2—C1—C2—S4 | −0.4 (7) | C16a—C11a—C12a—Cl1a | 175.4 (6) |
S1—C1—C2—S4 | −178.7 (3) | C11a—C12a—C13a—C14a | −0.2 (12) |
S2—C1—C2—S3 | 178.4 (3) | Cl1a—C12a—C13a—C14a | −178.0 (6) |
S1—C1—C2—S3 | 0.2 (7) | C11a—C12a—C13a—Cl2a | −179.5 (6) |
S1—C3—C4—S2 | 0.4 (6) | Cl1a—C12a—C13a—Cl2a | 2.6 (9) |
S5—C3—C4—S2 | −179.0 (4) | C12a—C13a—C14a—O2a | 178.2 (7) |
S1—C3—C4—S6 | −177.6 (3) | Cl2a—C13a—C14a—O2a | −2.4 (9) |
S5—C3—C4—S6 | 3.0 (8) | C12a—C13a—C14a—C15a | 2.5 (10) |
S3—C5—C6—S8 | 180.0 (3) | Cl2a—C13a—C14a—C15a | −178.0 (5) |
S7—C5—C6—S8 | 0.5 (9) | O2a—C14a—C15a—C16a | −177.8 (7) |
S3—C5—C6—S4 | −2.6 (6) | C13a—C14a—C15a—C16a | −2.2 (10) |
S7—C5—C6—S4 | 177.9 (3) | O2a—C14a—C15a—C17a | 3.5 (11) |
S5—C7—C8—S6 | 58.2 (6) | C13a—C14a—C15a—C17a | 179.1 (6) |
S7—C9—C10—S8 | −67.7 (7) | C17a—C15a—C16a—C18a | −6.2 (11) |
C2—C1—S1—C3 | 179.8 (5) | C14a—C15a—C16a—C18a | 175.2 (7) |
S2—C1—S1—C3 | 1.4 (4) | C17a—C15a—C16a—C11a | 178.2 (7) |
C4—C3—S1—C1 | −1.1 (5) | C14a—C15a—C16a—C11a | −0.5 (12) |
S5—C3—S1—C1 | 178.4 (3) | O1a—C11a—C16a—C15a | −176.5 (8) |
C2—C1—S2—C4 | −179.6 (5) | C12a—C11a—C16a—C15a | 2.8 (11) |
S1—C1—S2—C4 | −1.2 (4) | O1a—C11a—C16a—C18a | 7.7 (12) |
C3—C4—S2—C1 | 0.5 (5) | C12a—C11a—C16a—C18a | −173.0 (7) |
S6—C4—S2—C1 | 178.6 (4) | O1b—C11b—C12b—C13b | −174 (4) |
C1—C2—S3—C5 | −174.4 (5) | C16b—C11b—C12b—C13b | −2 (6) |
S4—C2—S3—C5 | 4.6 (4) | O1b—C11b—C12b—Cl1B | 8 (6) |
C6—C5—S3—C2 | −1.1 (5) | C16b—C11b—C12b—Cl1B | −180 (3) |
S7—C5—S3—C2 | 178.4 (3) | C11b—C12b—C13b—C14b | −4 (6) |
C1—C2—S4—C6 | 173.2 (5) | Cl1B—C12b—C13b—C14b | 174 (3) |
S3—C2—S4—C6 | −5.7 (4) | C11b—C12b—C13b—Cl2B | −176 (3) |
C5—C6—S4—C2 | 5.0 (5) | Cl1B—C12b—C13b—Cl2B | 2 (5) |
S8—C6—S4—C2 | −177.2 (3) | C12b—C13b—C14b—O2b | 178 (3) |
C4—C3—S5—C7 | −18.4 (6) | Cl2B—C13b—C14b—O2b | −9 (5) |
S1—C3—S5—C7 | 162.2 (3) | C12b—C13b—C14b—C15b | 6 (5) |
C8—C7—S5—C3 | −14.2 (6) | Cl2B—C13b—C14b—C15b | 179 (3) |
C3—C4—S6—C8 | 35.7 (6) | O2b—C14b—C15b—C16b | −176 (3) |
S2—C4—S6—C8 | −142.3 (4) | C13b—C14b—C15b—C16b | −3 (5) |
C7—C8—S6—C4 | −65.6 (5) | O2b—C14b—C15b—C17b | 7 (5) |
C6—C5—S7—C9 | −24.4 (6) | C13b—C14b—C15b—C17b | 180 (3) |
S3—C5—S7—C9 | 156.1 (4) | C17b—C15b—C16b—C18b | 2 (6) |
C10—C9—S7—C5 | 57.8 (5) | C14b—C15b—C16b—C18b | −175 (3) |
C5—C6—S8—C10 | −0.8 (6) | C17b—C15b—C16b—C11b | 175 (4) |
S4—C6—S8—C10 | −178.2 (4) | C14b—C15b—C16b—C11b | −2 (6) |
C9—C10—S8—C6 | 34.1 (6) | O1b—C11b—C16b—C15b | 177 (4) |
O1a—C11a—C12a—C13a | 176.8 (9) | C12b—C11b—C16b—C15b | 5 (6) |
C16a—C11a—C12a—C13a | −2.5 (11) | O1b—C11b—C16b—C18b | −10 (6) |
O1a—C11a—C12a—Cl1a | −5.3 (11) | C12b—C11b—C16b—C18b | 178 (4) |
The overlap integrals between the ET molecules. topIntermolecular contact | Direction | Overlap integral (S, × 103) |
ET1···ET2i | π-stack | 22.1 |
ET1···ET3ii | Side-by-side | 1.6 |
ET2···ET3iii | Side-by-side | 0.8 |
Symmetry codes: (i) -x, -y+1, -z+1;
(ii) x+1, y, z;
(iii) -x+1, -y+1, -z+1.] |