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Radical salts and charge-transfer complexes (CTCs) containing tetra­cyano­quinodi­methane (TCNQ) display electrical conductivity, which has led to the development of many TCNQ derivatives with enhanced electron-accepting properties that are applicable toward organic electronics. To expand the family of TCNQ derivatives, we report the synthesis and structures of 11,11,12,12-tetra­cyano-2,6-di­iodo-9,10-anthraquinodi­methane (abbreviated as DITCAQ), C20H6I2N4, and its charge-transfer complexes with various electron donors, namely DITCAQ–anthracene (2/1), C20H6I2N4·0.5C14H10, (I), DITCAQ–pyrene (2/1), C20H6I2N4·0.5C16H10, (II), and DITCAQ–tetra­thia­fulvalene (2/1), C20H6I2N4·0.5C6H4S4, (III). The mol­ecular structure of DITCAQ consists of a 2,6-di­iodo-9,10-di­hydro­anthracene moiety with two malono­nitrile substituents. DITCAQ possesses a saddle shape, since the malono­nitrile groups bend significantly up out of the plane of the central ring and the two benzene rings bend down out of the same plane. π–π inter­actions between DITCAQ and the electron-donor molecules control the degree of charge transfer in cocrystals (I), (II), and (III), which is reflected in both the dihedral angles between the terminal benzene ring and the central ring on the DITCAQ motifs, and their corresponding IR spectra.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616016387/yo3023sup1.cif
Contains datablocks DITCAQ, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016387/yo3023DITCAQsup2.hkl
Contains datablock DITCAQ

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016387/yo3023Isup3.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016387/yo3023IIsup4.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616016387/yo3023IIIsup5.hkl
Contains datablock III

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616016387/yo3023DITCAQsup6.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229616016387/yo3023sup10.pdf
NMR spectra

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616016387/yo3023Isup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616016387/yo3023IIsup8.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616016387/yo3023IIIsup9.cml
Supplementary material

CCDC references: 1509828; 1509827; 1509826; 1509825

Computing details top

For all compounds, data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: XPREP (Bruker, 2014) and SADABS (Bruker, 2014); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Bruker, 2014) and OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: XCIF (Bruker, 2014).

(DITCAQ) 11,11,12,12-Tetracyano-2,6-diiodo-9,10-anthraquinodimethane top
Crystal data top
C20H6I2N4Dx = 2.083 Mg m3
Mr = 556.09Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 9591 reflections
a = 8.7660 (3) Åθ = 2.5–27.1°
b = 12.2655 (4) ŵ = 3.56 mm1
c = 16.4903 (6) ÅT = 100 K
V = 1773.03 (11) Å3Prism, yellow
Z = 40.22 × 0.19 × 0.10 mm
F(000) = 1040
Data collection top
Bruker D8 Venture/Photon 100
diffractometer
3929 independent reflections
Radiation source: microfocus sealed tube3849 reflections with I > 2σ(I)
Multilayer mirrors monochromatorRint = 0.032
profile data from φ and ω scansθmax = 27.2°, θmin = 2.5°
Absorption correction: integration
(SADABS; Bruker, 2014)
h = 1111
Tmin = 0.999, Tmax = 1.000k = 1515
20684 measured reflectionsl = 2121
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.019 w = 1/[σ2(Fo2) + (0.023P)2 + 0.2251P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.045(Δ/σ)max = 0.001
S = 1.17Δρmax = 0.32 e Å3
3929 reflectionsΔρmin = 0.82 e Å3
235 parametersAbsolute structure: Flack (1983), with 1893 Friedel pairs
1 restraintAbsolute structure parameter: 0.016 (11)
Special details top

Experimental. One distinct cell was identified using APEX2 (Bruker, 2014). Five frame series were integrated and filtered for statistical outliers using SAINT (Bruker, 2013) then corrected for absorption by integration using SAINT/SADABS v2014/2 (Bruker, 2014) to sort, merge, and scale the combined data. No decay correction was applied.

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. Structure was phased by direct methods (Sheldrick, 2014). Systematic conditions suggested the unambiguous space group. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F2. The final map had no significant features. A final analysis of variance between observed and calculated structure factors showed little dependence on amplitude and resolution.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.61913 (3)0.27014 (2)0.38906 (2)0.01539 (7)
I20.42334 (4)1.10665 (2)0.58154 (2)0.01841 (8)
N10.2046 (5)0.4920 (3)0.7375 (3)0.0237 (10)
N20.0777 (5)0.8249 (3)0.7036 (3)0.0165 (8)
N30.1475 (5)0.4509 (3)0.2769 (3)0.0169 (8)
N40.0564 (5)0.7875 (3)0.2597 (3)0.0189 (9)
C10.5113 (5)0.3973 (3)0.4514 (3)0.0115 (8)
C20.5116 (5)0.3992 (3)0.5355 (3)0.0129 (9)
H20.55780.34120.56480.016*
C30.4448 (4)0.4851 (3)0.5772 (4)0.0118 (8)
H30.44730.48650.63480.014*
C40.3742 (5)0.5694 (4)0.5348 (3)0.0102 (8)
C50.3056 (5)0.6652 (3)0.5746 (3)0.0089 (7)
C60.3227 (5)0.7678 (3)0.5289 (3)0.0094 (8)
C70.3530 (5)0.8668 (3)0.5683 (3)0.0104 (8)
H70.36060.86960.62570.013*
C80.3719 (5)0.9610 (3)0.5220 (3)0.0115 (8)
C90.3597 (5)0.9587 (4)0.4374 (3)0.0125 (9)
H90.37141.02360.40660.015*
C100.3301 (5)0.8601 (3)0.3991 (3)0.0109 (8)
H100.32080.85800.34170.013*
C110.3139 (5)0.7638 (3)0.4439 (3)0.0100 (8)
C120.2931 (5)0.6562 (3)0.4056 (2)0.0100 (9)
C130.3704 (5)0.5654 (3)0.4487 (3)0.0104 (8)
C140.4406 (5)0.4798 (3)0.4077 (3)0.0117 (9)
H140.44010.47790.35010.014*
C150.2304 (5)0.6617 (4)0.6468 (3)0.0108 (8)
C160.2175 (5)0.5652 (4)0.6960 (3)0.0144 (9)
C170.1492 (5)0.7539 (3)0.6787 (3)0.0109 (9)
C180.2083 (5)0.6402 (3)0.3378 (3)0.0111 (8)
C190.1785 (5)0.5331 (3)0.3045 (3)0.0124 (9)
C200.1273 (5)0.7251 (4)0.2954 (3)0.0128 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01862 (14)0.01209 (12)0.01547 (13)0.00485 (10)0.00099 (13)0.00148 (13)
I20.02827 (16)0.01149 (13)0.01547 (14)0.00567 (11)0.00333 (14)0.00102 (12)
N10.027 (2)0.020 (2)0.024 (2)0.0023 (17)0.0077 (19)0.0104 (18)
N20.017 (2)0.020 (2)0.013 (2)0.0014 (15)0.0006 (16)0.0019 (16)
N30.020 (2)0.017 (2)0.0134 (19)0.0017 (15)0.0024 (16)0.0006 (16)
N40.020 (2)0.019 (2)0.018 (2)0.0005 (16)0.0038 (17)0.0033 (16)
C10.013 (2)0.0088 (19)0.013 (2)0.0010 (15)0.0013 (17)0.0020 (15)
C20.014 (2)0.0091 (19)0.016 (2)0.0002 (16)0.0028 (17)0.0029 (15)
C30.012 (2)0.0110 (17)0.0125 (19)0.0020 (15)0.001 (2)0.0053 (19)
C40.012 (2)0.009 (2)0.009 (2)0.0006 (15)0.0032 (16)0.0009 (15)
C50.0103 (19)0.0100 (17)0.0066 (18)0.0018 (14)0.0015 (18)0.0013 (16)
C60.009 (2)0.0090 (19)0.010 (2)0.0006 (15)0.0002 (16)0.0032 (15)
C70.014 (2)0.0086 (17)0.009 (2)0.0020 (15)0.0012 (16)0.0000 (15)
C80.015 (2)0.008 (2)0.012 (2)0.0002 (15)0.0026 (17)0.0010 (16)
C90.013 (2)0.011 (2)0.014 (2)0.0017 (16)0.0007 (17)0.0052 (16)
C100.0133 (19)0.0120 (17)0.007 (2)0.0017 (15)0.0021 (17)0.0023 (17)
C110.009 (2)0.0103 (19)0.010 (2)0.0027 (15)0.0025 (16)0.0006 (15)
C120.011 (2)0.0111 (19)0.008 (2)0.0000 (14)0.0024 (15)0.0024 (15)
C130.013 (2)0.011 (2)0.008 (2)0.0009 (16)0.0002 (16)0.0006 (15)
C140.012 (2)0.0106 (18)0.013 (2)0.0008 (15)0.0009 (15)0.0003 (15)
C150.013 (2)0.011 (2)0.009 (2)0.0014 (16)0.0022 (16)0.0018 (15)
C160.013 (2)0.018 (2)0.013 (2)0.0015 (16)0.0036 (17)0.0009 (19)
C170.011 (2)0.013 (2)0.008 (2)0.0043 (16)0.0007 (16)0.0024 (15)
C180.013 (2)0.011 (2)0.009 (2)0.0010 (16)0.0037 (16)0.0010 (15)
C190.012 (2)0.016 (2)0.009 (2)0.0024 (17)0.0011 (16)0.0019 (16)
C200.017 (2)0.014 (2)0.007 (2)0.0001 (17)0.0004 (16)0.0011 (16)
Geometric parameters (Å, º) top
I1—C12.094 (4)C6—C111.405 (6)
I2—C82.089 (4)C7—C81.395 (6)
N1—C161.135 (6)C7—H70.9500
N2—C171.148 (6)C8—C91.399 (6)
N3—C191.139 (6)C9—C101.388 (6)
N4—C201.148 (6)C9—H90.9500
C1—C21.386 (6)C10—C111.402 (6)
C1—C141.389 (6)C10—H100.9500
C2—C31.388 (6)C11—C121.473 (6)
C2—H20.9500C12—C181.357 (6)
C3—C41.393 (6)C12—C131.485 (6)
C3—H30.9500C13—C141.393 (6)
C4—C131.420 (6)C14—H140.9500
C4—C51.475 (6)C15—C171.437 (6)
C5—C151.361 (6)C15—C161.439 (6)
C5—C61.475 (5)C18—C201.442 (6)
C6—C71.402 (6)C18—C191.448 (6)
C2—C1—C14120.5 (4)C8—C9—H9120.5
C2—C1—I1120.2 (3)C9—C10—C11120.9 (4)
C14—C1—I1119.3 (3)C9—C10—H10119.6
C1—C2—C3120.5 (4)C11—C10—H10119.6
C1—C2—H2119.7C10—C11—C6119.4 (4)
C3—C2—H2119.7C10—C11—C12122.8 (4)
C2—C3—C4120.1 (5)C6—C11—C12117.8 (4)
C2—C3—H3120.0C18—C12—C11123.4 (4)
C4—C3—H3120.0C18—C12—C13122.4 (4)
C3—C4—C13119.2 (4)C11—C12—C13114.2 (4)
C3—C4—C5123.2 (4)C14—C13—C4120.1 (4)
C13—C4—C5117.6 (4)C14—C13—C12122.3 (4)
C15—C5—C4124.2 (4)C4—C13—C12117.6 (4)
C15—C5—C6121.5 (4)C1—C14—C13119.6 (4)
C4—C5—C6114.3 (4)C1—C14—H14120.2
C7—C6—C11120.2 (4)C13—C14—H14120.2
C7—C6—C5121.4 (4)C5—C15—C17122.4 (4)
C11—C6—C5118.3 (4)C5—C15—C16123.8 (4)
C8—C7—C6119.1 (4)C17—C15—C16113.7 (4)
C8—C7—H7120.5N1—C16—C15176.9 (5)
C6—C7—H7120.5N2—C17—C15176.6 (5)
C7—C8—C9121.4 (4)C12—C18—C20124.4 (4)
C7—C8—I2118.5 (3)C12—C18—C19122.9 (4)
C9—C8—I2120.2 (3)C20—C18—C19112.5 (4)
C10—C9—C8119.0 (4)N3—C19—C18176.3 (5)
C10—C9—H9120.5N4—C20—C18175.5 (5)
C14—C1—C2—C31.8 (7)C5—C6—C11—C121.9 (6)
I1—C1—C2—C3177.8 (3)C10—C11—C12—C1837.7 (7)
C1—C2—C3—C41.3 (7)C6—C11—C12—C18144.4 (4)
C2—C3—C4—C130.6 (6)C10—C11—C12—C13143.6 (4)
C2—C3—C4—C5177.8 (4)C6—C11—C12—C1334.3 (6)
C3—C4—C5—C1536.5 (7)C3—C4—C13—C141.9 (6)
C13—C4—C5—C15145.1 (4)C5—C4—C13—C14176.6 (4)
C3—C4—C5—C6144.3 (4)C3—C4—C13—C12179.5 (4)
C13—C4—C5—C634.0 (6)C5—C4—C13—C122.0 (6)
C15—C5—C6—C739.8 (6)C18—C12—C13—C1439.1 (6)
C4—C5—C6—C7141.0 (4)C11—C12—C13—C14142.2 (4)
C15—C5—C6—C11142.7 (5)C18—C12—C13—C4142.4 (4)
C4—C5—C6—C1136.5 (6)C11—C12—C13—C436.3 (5)
C11—C6—C7—C81.0 (7)C2—C1—C14—C130.5 (7)
C5—C6—C7—C8178.4 (4)I1—C1—C14—C13179.2 (3)
C6—C7—C8—C90.6 (7)C4—C13—C14—C11.4 (6)
C6—C7—C8—I2178.2 (3)C12—C13—C14—C1179.9 (4)
C7—C8—C9—C100.9 (7)C4—C5—C15—C17172.1 (4)
I2—C8—C9—C10178.0 (3)C6—C5—C15—C176.9 (7)
C8—C9—C10—C110.5 (7)C4—C5—C15—C164.4 (7)
C9—C10—C11—C62.1 (7)C6—C5—C15—C16176.5 (4)
C9—C10—C11—C12175.7 (4)C11—C12—C18—C200.6 (7)
C7—C6—C11—C102.3 (7)C13—C12—C18—C20178.0 (4)
C5—C6—C11—C10179.9 (4)C11—C12—C18—C19174.8 (4)
C7—C6—C11—C12175.6 (4)C13—C12—C18—C193.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···I2i0.953.123.748 (4)125
C7—H7···N3ii0.952.693.592 (6)160
Symmetry codes: (i) x, y1, z; (ii) x+1/2, y+1/2, z+1/2.
(I) 11,11,12,12-Tetracyano-2,6-diiodo-9,10-anthraquinodimethane–anthracene (2/1) top
Crystal data top
C20H6I2N4·0.5(C14H10)F(000) = 1228
Mr = 645.20Dx = 1.825 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 13.7727 (9) ÅCell parameters from 8277 reflections
b = 8.5843 (5) Åθ = 2.6–27.2°
c = 20.5752 (13) ŵ = 2.70 mm1
β = 105.115 (3)°T = 273 K
V = 2348.4 (3) Å3Plate, orange
Z = 40.22 × 0.21 × 0.08 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5201 independent reflections
Radiation source: fine-focus sealed tube4344 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
profile data from ω scansθmax = 27.2°, θmin = 2.8°
Absorption correction: integration
(SADABS; Bruker, 2014)
h = 1717
Tmin = 0.681, Tmax = 0.879k = 1111
21378 measured reflectionsl = 2621
Refinement top
Refinement on F2198 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.073 w = 1/[σ2(Fo2) + (0.0255P)2 + 1.9565P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.002
5201 reflectionsΔρmax = 0.87 e Å3
362 parametersΔρmin = 0.92 e Å3
Special details top

Experimental. One distinct cell was identified using APEX2 (Bruker, 2014). Four frame series were integrated and filtered for statistical outliers using SAINT (Bruker, 2013) then corrected for absorption by integration using SADABS v2014/2 (Bruker, 2014). No decay correction was applied.

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. Structure was phased by direct methods (Sheldrick, 2014). Systematic conditions suggested the unambiguous space group. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F2. The highest peaks in the final difference Fourier map were in the vicinity of atoms I2 and I1; the final map had no other significant features. A final analysis of variance between observed and calculated structure factors showed little dependence on amplitude or resolution.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
I10.80023 (2)0.06182 (2)0.27495 (2)0.04243 (7)
I20.88708 (2)0.07183 (3)0.81408 (2)0.05564 (8)
N10.4533 (2)0.2878 (4)0.46726 (16)0.0570 (8)
N20.5193 (2)0.0972 (4)0.66344 (16)0.0587 (8)
N30.6795 (2)0.4264 (3)0.37357 (14)0.0514 (7)
N40.7651 (2)0.5770 (3)0.57558 (14)0.0457 (6)
C10.7533 (2)0.0610 (3)0.36362 (14)0.0319 (6)
C20.7029 (2)0.1914 (3)0.37856 (14)0.0358 (6)
H2A0.68860.27440.34860.043*
C30.6745 (2)0.1969 (3)0.43776 (14)0.0322 (6)
H3A0.64130.28470.44760.039*
C40.69455 (19)0.0733 (3)0.48342 (13)0.0268 (5)
C50.66956 (19)0.0753 (3)0.54877 (13)0.0270 (5)
C60.74263 (18)0.0061 (3)0.60332 (13)0.0274 (5)
C70.7695 (2)0.0525 (3)0.66834 (14)0.0338 (6)
H7A0.73920.14240.67890.041*
C80.8421 (2)0.0244 (4)0.71756 (14)0.0368 (6)
C90.8860 (2)0.1599 (3)0.70255 (14)0.0387 (6)
H9A0.93350.21160.73610.046*
C100.8594 (2)0.2183 (3)0.63781 (14)0.0335 (6)
H10A0.88870.31000.62810.040*
C110.78929 (18)0.1415 (3)0.58699 (12)0.0267 (5)
C120.76325 (18)0.1893 (3)0.51620 (12)0.0257 (5)
C130.74330 (18)0.0599 (3)0.46719 (13)0.0261 (5)
C140.77265 (19)0.0651 (3)0.40707 (13)0.0289 (5)
H14A0.80500.15270.39630.035*
C150.58413 (19)0.1388 (3)0.55841 (13)0.0302 (5)
C160.5121 (2)0.2219 (3)0.50680 (16)0.0378 (6)
C170.5517 (2)0.1170 (3)0.61862 (15)0.0378 (6)
C180.75180 (19)0.3408 (3)0.49645 (13)0.0284 (5)
C190.7134 (2)0.3856 (3)0.42720 (15)0.0339 (6)
C200.7616 (2)0.4700 (3)0.54249 (14)0.0321 (6)
C210.0347 (13)0.5813 (15)0.6384 (6)0.056 (2)0.64 (3)
H21A0.05810.50700.67170.067*0.64 (3)
C220.0138 (8)0.7271 (17)0.6548 (6)0.056 (2)0.64 (3)
H22A0.02360.75380.69990.067*0.64 (3)
C230.0229 (8)0.8398 (13)0.6045 (8)0.056 (2)0.64 (3)
H23A0.03570.94030.61690.067*0.64 (3)
C240.0399 (11)0.8040 (13)0.5380 (7)0.0518 (18)0.64 (3)
H24A0.06410.88000.50560.062*0.64 (3)
C250.021 (2)0.6496 (16)0.5176 (5)0.0454 (16)0.64 (3)
C260.0409 (12)0.6062 (14)0.4505 (5)0.0456 (19)0.64 (3)
H26A0.06910.67890.41750.055*0.64 (3)
C270.0204 (18)0.4574 (16)0.4311 (8)0.042 (2)0.64 (3)
C21B0.044 (2)0.539 (3)0.6403 (11)0.057 (3)0.36 (3)
H21B0.07320.45910.66930.068*0.36 (3)
C22B0.0259 (15)0.675 (3)0.6669 (10)0.060 (3)0.36 (3)
H22B0.03910.68450.71340.072*0.36 (3)
C23B0.0122 (14)0.805 (2)0.6262 (12)0.054 (3)0.36 (3)
H23B0.02240.89860.64620.065*0.36 (3)
C24B0.034 (2)0.795 (2)0.5578 (11)0.050 (3)0.36 (3)
H24B0.06040.88030.53130.060*0.36 (3)
C25B0.017 (4)0.651 (3)0.5271 (9)0.046 (2)0.36 (3)
C26B0.033 (2)0.632 (3)0.4583 (10)0.043 (2)0.36 (3)
H26B0.05320.71750.43030.052*0.36 (3)
C27B0.020 (3)0.489 (3)0.4299 (14)0.042 (3)0.36 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.05931 (14)0.04209 (12)0.02975 (12)0.00404 (8)0.01848 (9)0.00580 (7)
I20.05716 (15)0.07823 (18)0.02677 (12)0.00482 (11)0.00242 (9)0.01191 (9)
N10.0429 (15)0.0708 (19)0.0576 (19)0.0154 (14)0.0139 (14)0.0189 (15)
N20.0556 (18)0.078 (2)0.0482 (19)0.0041 (15)0.0231 (15)0.0130 (15)
N30.081 (2)0.0377 (14)0.0370 (16)0.0103 (13)0.0181 (14)0.0064 (11)
N40.0576 (17)0.0324 (13)0.0470 (16)0.0002 (11)0.0134 (13)0.0047 (11)
C10.0389 (14)0.0324 (13)0.0255 (14)0.0057 (11)0.0103 (11)0.0009 (10)
C20.0471 (16)0.0272 (13)0.0322 (15)0.0005 (11)0.0087 (12)0.0050 (11)
C30.0384 (15)0.0237 (12)0.0342 (15)0.0001 (10)0.0091 (11)0.0022 (10)
C40.0296 (13)0.0249 (12)0.0246 (13)0.0029 (9)0.0048 (10)0.0034 (9)
C50.0296 (13)0.0224 (11)0.0280 (13)0.0027 (9)0.0055 (10)0.0045 (9)
C60.0281 (13)0.0288 (12)0.0253 (13)0.0014 (10)0.0069 (10)0.0018 (10)
C70.0358 (14)0.0376 (14)0.0281 (14)0.0009 (11)0.0087 (11)0.0057 (11)
C80.0385 (15)0.0501 (17)0.0213 (14)0.0049 (12)0.0068 (11)0.0027 (11)
C90.0373 (15)0.0478 (17)0.0291 (15)0.0014 (12)0.0053 (12)0.0085 (12)
C100.0374 (14)0.0328 (14)0.0305 (14)0.0046 (11)0.0095 (11)0.0042 (11)
C110.0279 (12)0.0274 (12)0.0244 (13)0.0029 (10)0.0062 (10)0.0002 (10)
C120.0243 (12)0.0271 (12)0.0263 (13)0.0012 (9)0.0078 (10)0.0002 (10)
C130.0274 (12)0.0250 (12)0.0257 (13)0.0029 (10)0.0064 (10)0.0016 (9)
C140.0330 (13)0.0266 (12)0.0284 (14)0.0004 (10)0.0101 (11)0.0028 (10)
C150.0317 (13)0.0273 (12)0.0305 (14)0.0005 (10)0.0060 (11)0.0053 (10)
C160.0337 (15)0.0376 (15)0.0431 (17)0.0017 (12)0.0118 (13)0.0022 (13)
C170.0345 (15)0.0410 (15)0.0380 (17)0.0011 (12)0.0093 (12)0.0092 (12)
C180.0311 (13)0.0268 (12)0.0288 (13)0.0030 (10)0.0105 (10)0.0010 (10)
C190.0477 (16)0.0225 (12)0.0347 (16)0.0017 (11)0.0163 (13)0.0024 (11)
C200.0362 (14)0.0285 (13)0.0323 (15)0.0015 (10)0.0103 (11)0.0028 (11)
C210.043 (4)0.057 (6)0.064 (4)0.002 (4)0.010 (3)0.002 (4)
C220.044 (3)0.058 (5)0.064 (4)0.003 (4)0.010 (3)0.006 (4)
C230.036 (3)0.056 (4)0.073 (5)0.007 (3)0.011 (3)0.007 (4)
C240.034 (3)0.051 (3)0.069 (4)0.003 (2)0.011 (4)0.005 (3)
C250.026 (3)0.042 (3)0.068 (4)0.001 (2)0.011 (4)0.001 (3)
C260.030 (3)0.042 (4)0.061 (3)0.002 (3)0.005 (3)0.006 (3)
C270.025 (3)0.039 (5)0.062 (3)0.004 (5)0.010 (2)0.002 (4)
C21B0.035 (5)0.058 (7)0.070 (5)0.004 (6)0.002 (4)0.004 (5)
C22B0.043 (4)0.061 (6)0.071 (5)0.003 (5)0.003 (4)0.007 (5)
C23B0.039 (4)0.055 (5)0.068 (6)0.009 (4)0.011 (5)0.010 (4)
C24B0.031 (4)0.049 (4)0.069 (6)0.006 (3)0.012 (5)0.008 (5)
C25B0.028 (4)0.046 (4)0.066 (5)0.001 (4)0.013 (5)0.006 (4)
C26B0.028 (4)0.035 (5)0.065 (4)0.001 (4)0.011 (4)0.000 (4)
C27B0.028 (4)0.036 (7)0.060 (5)0.002 (6)0.009 (4)0.004 (5)
Geometric parameters (Å, º) top
I1—C12.089 (3)C18—C191.437 (4)
I2—C82.090 (3)C18—C201.442 (4)
N1—C161.138 (4)C21—C221.347 (8)
N2—C171.137 (4)C21—C27i1.43 (2)
N3—C191.136 (4)C21—H21A0.9300
N4—C201.137 (4)C22—C231.411 (8)
C1—C141.385 (4)C22—H22A0.9300
C1—C21.392 (4)C23—C241.361 (8)
C2—C31.374 (4)C23—H23A0.9300
C2—H2A0.9300C24—C251.435 (6)
C3—C41.397 (4)C24—H24A0.9300
C3—H3A0.9300C25—C261.385 (7)
C4—C131.409 (3)C25—C27i1.40 (2)
C4—C51.472 (4)C26—C271.389 (7)
C5—C151.358 (3)C26—H26A0.9300
C5—C61.474 (4)C27—C25i1.40 (2)
C6—C71.386 (4)C27—C21i1.43 (2)
C6—C111.410 (3)C21B—C22B1.343 (10)
C7—C81.390 (4)C21B—C27Bi1.41 (4)
C7—H7A0.9300C21B—H21B0.9300
C8—C91.383 (4)C22B—C23B1.410 (10)
C9—C101.380 (4)C22B—H22B0.9300
C9—H9A0.9300C23B—C24B1.363 (10)
C10—C111.390 (4)C23B—H23B0.9300
C10—H10A0.9300C24B—C25B1.436 (8)
C11—C121.465 (3)C24B—H24B0.9300
C12—C181.359 (3)C25B—C26B1.383 (9)
C12—C131.477 (3)C25B—C27Bi1.50 (4)
C13—C141.399 (4)C26B—C27B1.390 (9)
C14—H14A0.9300C26B—H26B0.9300
C15—C171.435 (4)C27B—C21Bi1.42 (4)
C15—C161.439 (4)C27B—C25Bi1.50 (4)
C14—C1—C2120.6 (2)C12—C18—C19122.5 (2)
C14—C1—I1120.99 (19)C12—C18—C20123.8 (2)
C2—C1—I1118.40 (19)C19—C18—C20113.1 (2)
C3—C2—C1119.8 (2)N3—C19—C18176.2 (3)
C3—C2—H2A120.1N4—C20—C18175.6 (3)
C1—C2—H2A120.1C22—C21—C27i118.9 (10)
C2—C3—C4121.2 (2)C22—C21—H21A120.5
C2—C3—H3A119.4C27i—C21—H21A120.5
C4—C3—H3A119.4C21—C22—C23120.8 (6)
C3—C4—C13118.7 (2)C21—C22—H22A119.6
C3—C4—C5123.6 (2)C23—C22—H22A119.6
C13—C4—C5117.7 (2)C24—C23—C22121.2 (6)
C15—C5—C4123.8 (2)C24—C23—H23A119.4
C15—C5—C6121.7 (2)C22—C23—H23A119.4
C4—C5—C6114.5 (2)C23—C24—C25120.4 (6)
C7—C6—C11120.4 (2)C23—C24—H24A119.8
C7—C6—C5121.4 (2)C25—C24—H24A119.8
C11—C6—C5118.2 (2)C26—C25—C27i120.6 (10)
C6—C7—C8119.4 (2)C26—C25—C24122.4 (7)
C6—C7—H7A120.3C27i—C25—C24117.0 (9)
C8—C7—H7A120.3C25—C26—C27122.0 (7)
C9—C8—C7120.7 (3)C25—C26—H26A119.0
C9—C8—I2120.4 (2)C27—C26—H26A119.0
C7—C8—I2118.9 (2)C26—C27—C25i117.3 (11)
C10—C9—C8120.0 (3)C26—C27—C21i121.0 (11)
C10—C9—H9A120.0C25i—C27—C21i121.5 (11)
C8—C9—H9A120.0C22B—C21B—C27Bi123.2 (17)
C9—C10—C11120.7 (3)C22B—C21B—H21B118.4
C9—C10—H10A119.6C27Bi—C21B—H21B118.4
C11—C10—H10A119.6C21B—C22B—C23B121.7 (11)
C10—C11—C6118.8 (2)C21B—C22B—H22B119.1
C10—C11—C12123.8 (2)C23B—C22B—H22B119.1
C6—C11—C12117.3 (2)C24B—C23B—C22B120.7 (9)
C18—C12—C11123.0 (2)C24B—C23B—H23B119.6
C18—C12—C13121.9 (2)C22B—C23B—H23B119.6
C11—C12—C13114.9 (2)C23B—C24B—C25B119.5 (10)
C14—C13—C4120.1 (2)C23B—C24B—H24B120.2
C14—C13—C12122.3 (2)C25B—C24B—H24B120.2
C4—C13—C12117.6 (2)C26B—C25B—C24B123.4 (12)
C1—C14—C13119.6 (2)C26B—C25B—C27Bi116.7 (17)
C1—C14—H14A120.2C24B—C25B—C27Bi119.9 (16)
C13—C14—H14A120.2C25B—C26B—C27B122.0 (13)
C5—C15—C17123.4 (3)C25B—C26B—H26B119.0
C5—C15—C16123.3 (2)C27B—C26B—H26B119.0
C17—C15—C16113.1 (2)C26B—C27B—C21Bi124 (2)
N1—C16—C15178.0 (3)C26B—C27B—C25Bi121 (2)
N2—C17—C15175.1 (3)C21Bi—C27B—C25Bi114.7 (19)
C14—C1—C2—C31.7 (4)C18—C12—C13—C1441.2 (4)
I1—C1—C2—C3177.5 (2)C11—C12—C13—C14142.8 (2)
C1—C2—C3—C40.4 (4)C18—C12—C13—C4140.0 (3)
C2—C3—C4—C131.1 (4)C11—C12—C13—C436.0 (3)
C2—C3—C4—C5177.5 (2)C2—C1—C14—C131.4 (4)
C3—C4—C5—C1538.6 (4)I1—C1—C14—C13177.79 (19)
C13—C4—C5—C15142.9 (2)C4—C13—C14—C10.2 (4)
C3—C4—C5—C6144.8 (2)C12—C13—C14—C1179.0 (2)
C13—C4—C5—C633.8 (3)C4—C5—C15—C17168.8 (2)
C15—C5—C6—C742.4 (4)C6—C5—C15—C177.7 (4)
C4—C5—C6—C7140.9 (2)C4—C5—C15—C164.9 (4)
C15—C5—C6—C11141.1 (2)C6—C5—C15—C16178.7 (2)
C4—C5—C6—C1135.6 (3)C11—C12—C18—C19171.6 (2)
C11—C6—C7—C80.7 (4)C13—C12—C18—C194.1 (4)
C5—C6—C7—C8177.1 (2)C11—C12—C18—C201.5 (4)
C6—C7—C8—C91.3 (4)C13—C12—C18—C20174.2 (2)
C6—C7—C8—I2176.85 (19)C27i—C21—C22—C231 (2)
C7—C8—C9—C101.3 (4)C21—C22—C23—C241.2 (14)
I2—C8—C9—C10176.8 (2)C22—C23—C24—C250.0 (18)
C8—C9—C10—C110.7 (4)C23—C24—C25—C26177.2 (19)
C9—C10—C11—C62.6 (4)C23—C24—C25—C27i3 (3)
C9—C10—C11—C12174.9 (2)C27i—C25—C26—C271 (4)
C7—C6—C11—C102.6 (4)C24—C25—C26—C27178.8 (18)
C5—C6—C11—C10179.2 (2)C25—C26—C27—C25i1 (4)
C7—C6—C11—C12175.1 (2)C25—C26—C27—C21i175 (2)
C5—C6—C11—C121.5 (3)C27Bi—C21B—C22B—C23B4 (4)
C10—C11—C12—C1840.7 (4)C21B—C22B—C23B—C24B1 (3)
C6—C11—C12—C18141.7 (3)C22B—C23B—C24B—C25B1 (3)
C10—C11—C12—C13143.3 (2)C23B—C24B—C25B—C26B177 (4)
C6—C11—C12—C1334.2 (3)C23B—C24B—C25B—C27Bi4 (6)
C3—C4—C13—C141.4 (4)C24B—C25B—C26B—C27B177 (3)
C5—C4—C13—C14177.2 (2)C27Bi—C25B—C26B—C27B2 (7)
C3—C4—C13—C12179.7 (2)C25B—C26B—C27B—C21Bi174 (4)
C5—C4—C13—C121.6 (3)C25B—C26B—C27B—C25Bi2 (7)
Symmetry code: (i) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N3ii0.932.633.296 (4)129
C9—H9···N2iii0.932.593.432 (4)151
Symmetry codes: (ii) x, y1, z; (iii) x+3/2, y+1/2, z+3/2.
(II) 11,11,12,12-Tetracyano-2,6-diiodo-9,10-anthraquinodimethane–pyrene (2/1) top
Crystal data top
C20H6I2N4·0.5C16H10Z = 2
Mr = 657.21F(000) = 626
Triclinic, P1Dx = 1.789 Mg m3
a = 8.7758 (13) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.0214 (17) ÅCell parameters from 9953 reflections
c = 13.3155 (19) Åθ = 2.5–24.9°
α = 66.461 (7)°µ = 2.60 mm1
β = 74.489 (7)°T = 273 K
γ = 74.462 (7)°Prism, red
V = 1220.2 (3) Å30.16 × 0.10 × 0.10 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4480 independent reflections
Radiation source: fine-focus sealed tube3844 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
profile data from φ and ω scansθmax = 25.4°, θmin = 2.6°
Absorption correction: integration
(SADABS; Bruker, 2014)
h = 1010
Tmin = 0.734, Tmax = 0.845k = 1414
30806 measured reflectionsl = 1616
Refinement top
Refinement on F2500 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0337P)2 + 2.3821P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.004
4480 reflectionsΔρmax = 0.97 e Å3
426 parametersΔρmin = 1.26 e Å3
Special details top

Experimental. One distinct cell was identified using APEX2 (Bruker, 2014). Sixteen frame series were integrated and filtered for statistical outliers using SAINT (Bruker, 2013) then corrected for absorption by integration using SAINT/SADABS v2014/2 (Bruker, 2014) to sort, merge, and scale the combined data. No decay correction was applied.

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. Structure was phased by direct methods (Sheldrick, 2014). Systematic conditions suggested the ambiguous space group. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F2. The highest peaks in the final difference Fourier map were in the vicinity of the I atoms; the final map had no other significant features. A final analysis of variance between observed and calculated structure factors showed little dependence on amplitude and resolution.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
I10.74790 (3)0.05020 (3)0.02608 (3)0.05572 (11)
I20.25760 (5)0.70674 (4)0.39302 (3)0.08814 (16)
N31.0893 (4)0.0496 (4)0.2266 (4)0.0612 (10)
N41.0585 (4)0.3343 (4)0.3431 (3)0.0604 (10)
C10.6463 (4)0.1005 (3)0.1143 (3)0.0403 (8)
C20.4964 (5)0.0764 (4)0.1738 (3)0.0455 (9)
H2A0.44300.03250.15470.055*
C30.4261 (4)0.1174 (4)0.2614 (3)0.0427 (9)
H3A0.32430.10220.30020.051*
C40.5047 (4)0.1814 (3)0.2930 (3)0.0348 (7)
C50.4328 (4)0.2329 (4)0.3821 (3)0.0376 (8)
C60.4791 (4)0.3502 (4)0.3616 (3)0.0386 (8)
C70.3711 (5)0.4462 (4)0.3893 (3)0.0490 (10)
H7A0.26650.43650.42560.059*
C80.4206 (5)0.5564 (4)0.3626 (4)0.0536 (11)
C90.5766 (6)0.5720 (4)0.3116 (4)0.0543 (10)
H9A0.60880.64570.29630.065*
C100.6838 (5)0.4775 (4)0.2839 (3)0.0445 (9)
H10A0.78890.48770.24960.053*
C110.6374 (4)0.3668 (3)0.3062 (3)0.0354 (8)
C120.7432 (4)0.2682 (3)0.2693 (3)0.0331 (7)
C130.6602 (4)0.2015 (3)0.2344 (3)0.0333 (7)
C140.7291 (4)0.1620 (3)0.1449 (3)0.0368 (8)
H14A0.83090.17670.10530.044*
N10.261 (2)0.0356 (14)0.5130 (14)0.055 (3)0.61 (4)
N20.243 (2)0.2268 (19)0.6549 (11)0.070 (3)0.61 (4)
C150.339 (4)0.171 (2)0.4769 (15)0.043 (3)0.61 (4)
C160.296 (2)0.0552 (17)0.4970 (16)0.045 (3)0.61 (4)
C170.288 (2)0.2053 (16)0.5739 (10)0.049 (3)0.61 (4)
N1B0.215 (3)0.010 (2)0.524 (2)0.060 (5)0.39 (4)
N2B0.204 (3)0.273 (3)0.6355 (19)0.067 (4)0.39 (4)
C15B0.329 (6)0.185 (4)0.477 (2)0.044 (3)0.39 (4)
C16B0.271 (4)0.074 (3)0.501 (3)0.049 (4)0.39 (4)
C17B0.258 (3)0.238 (3)0.5619 (17)0.049 (3)0.39 (4)
C180.9032 (4)0.2366 (3)0.2703 (3)0.0355 (8)
C191.0039 (4)0.1322 (4)0.2438 (3)0.0428 (9)
C200.9868 (4)0.2937 (4)0.3109 (3)0.0423 (9)
C210.791 (3)0.682 (3)1.026 (3)0.077 (3)0.640 (6)
H210.70010.74231.02790.093*0.640 (6)
C220.7924 (10)0.5881 (8)0.9795 (7)0.065 (2)0.640 (6)
C230.6650 (11)0.5838 (9)0.9391 (7)0.080 (2)0.640 (6)
H230.57050.64160.94050.096*0.640 (6)
C240.6792 (11)0.4963 (9)0.8984 (8)0.075 (2)0.640 (6)
H240.59050.49470.87370.090*0.640 (6)
C250.8082 (12)0.4116 (9)0.8901 (8)0.072 (2)0.640 (6)
H250.81130.35640.85640.087*0.640 (6)
C260.9347 (10)0.4972 (9)0.9790 (10)0.0555 (19)0.640 (6)
C270.9463 (11)0.4059 (7)0.9347 (6)0.0643 (16)0.640 (6)
C281.0891 (13)0.3172 (8)0.9353 (8)0.074 (2)0.640 (6)
H281.09730.25600.90710.089*0.640 (6)
C21B0.725 (2)0.6277 (15)0.9780 (15)0.076 (3)0.360 (6)
H21B0.62080.65970.96490.092*0.360 (6)
C22B0.8136 (15)0.5211 (12)0.9446 (11)0.066 (2)0.360 (6)
C23B0.760 (2)0.4655 (16)0.8895 (16)0.075 (3)0.360 (6)
H23B0.65860.49410.87070.091*0.360 (6)
C24B0.8581 (19)0.3703 (13)0.8642 (13)0.074 (3)0.360 (6)
H24B0.82030.33710.82530.089*0.360 (6)
C25B0.9996 (18)0.3197 (13)0.8881 (12)0.076 (3)0.360 (6)
H25B1.05840.25250.86810.091*0.360 (6)
C26B0.9703 (18)0.4736 (15)0.9718 (19)0.057 (3)0.360 (6)
C27B1.0654 (18)0.3699 (12)0.9470 (12)0.065 (3)0.360 (6)
C28B1.219 (4)0.323 (5)0.978 (6)0.073 (5)0.360 (6)
H28B1.28010.25210.96500.088*0.360 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.05144 (17)0.0706 (2)0.0640 (2)0.01313 (14)0.00780 (13)0.04343 (16)
I20.0970 (3)0.0790 (3)0.0804 (3)0.0256 (2)0.0165 (2)0.0463 (2)
N30.040 (2)0.075 (3)0.078 (3)0.0009 (19)0.0118 (18)0.043 (2)
N40.045 (2)0.074 (3)0.079 (3)0.0132 (18)0.0216 (19)0.036 (2)
C10.040 (2)0.043 (2)0.043 (2)0.0046 (16)0.0134 (16)0.0184 (17)
C20.043 (2)0.049 (2)0.053 (2)0.0155 (18)0.0151 (18)0.0185 (19)
C30.0317 (19)0.053 (2)0.045 (2)0.0156 (17)0.0081 (16)0.0122 (18)
C40.0292 (17)0.0400 (19)0.0331 (18)0.0068 (14)0.0108 (14)0.0073 (15)
C50.0251 (17)0.052 (2)0.0333 (18)0.0049 (15)0.0088 (14)0.0117 (16)
C60.0350 (19)0.051 (2)0.0308 (18)0.0052 (16)0.0088 (15)0.0153 (16)
C70.041 (2)0.066 (3)0.040 (2)0.0015 (19)0.0080 (17)0.024 (2)
C80.062 (3)0.054 (3)0.047 (2)0.012 (2)0.019 (2)0.028 (2)
C90.068 (3)0.046 (2)0.053 (2)0.009 (2)0.017 (2)0.019 (2)
C100.046 (2)0.047 (2)0.043 (2)0.0114 (18)0.0094 (17)0.0162 (18)
C110.0360 (18)0.0412 (19)0.0299 (17)0.0060 (15)0.0112 (14)0.0108 (15)
C120.0319 (17)0.0392 (19)0.0271 (17)0.0126 (15)0.0039 (13)0.0076 (14)
C130.0298 (17)0.0363 (18)0.0327 (18)0.0080 (14)0.0097 (14)0.0073 (15)
C140.0321 (18)0.044 (2)0.0352 (19)0.0114 (15)0.0057 (14)0.0121 (16)
N10.046 (7)0.051 (6)0.050 (5)0.006 (5)0.006 (5)0.011 (4)
N20.077 (7)0.077 (8)0.049 (5)0.008 (6)0.002 (4)0.023 (5)
C150.029 (4)0.058 (5)0.038 (3)0.007 (5)0.007 (3)0.015 (3)
C160.031 (5)0.057 (6)0.037 (3)0.006 (5)0.001 (3)0.010 (3)
C170.038 (5)0.058 (6)0.043 (4)0.006 (4)0.004 (3)0.015 (4)
N1B0.040 (8)0.056 (9)0.057 (7)0.005 (7)0.014 (7)0.010 (6)
N2B0.062 (9)0.074 (10)0.056 (7)0.010 (7)0.003 (6)0.021 (7)
C15B0.029 (5)0.059 (6)0.039 (4)0.010 (6)0.006 (4)0.012 (4)
C16B0.031 (6)0.059 (6)0.040 (5)0.003 (6)0.000 (4)0.007 (5)
C17B0.035 (6)0.064 (7)0.041 (5)0.008 (6)0.007 (4)0.012 (5)
C180.0311 (18)0.043 (2)0.0333 (18)0.0131 (15)0.0035 (14)0.0123 (15)
C190.0318 (19)0.057 (2)0.046 (2)0.0125 (18)0.0076 (16)0.0209 (19)
C200.0316 (19)0.054 (2)0.044 (2)0.0098 (17)0.0068 (16)0.0184 (18)
C210.078 (5)0.052 (5)0.066 (5)0.005 (4)0.002 (4)0.001 (4)
C220.061 (3)0.058 (4)0.051 (3)0.012 (3)0.007 (3)0.005 (3)
C230.073 (4)0.075 (4)0.063 (3)0.012 (3)0.014 (3)0.005 (3)
C240.077 (4)0.074 (4)0.063 (3)0.022 (3)0.019 (3)0.002 (3)
C250.087 (4)0.062 (4)0.062 (3)0.021 (3)0.009 (3)0.014 (3)
C260.065 (4)0.048 (3)0.040 (3)0.020 (3)0.005 (3)0.002 (3)
C270.079 (3)0.056 (3)0.049 (3)0.023 (3)0.009 (3)0.004 (2)
C280.093 (4)0.054 (4)0.059 (4)0.017 (4)0.005 (3)0.008 (3)
C21B0.072 (5)0.065 (5)0.065 (4)0.012 (4)0.007 (4)0.001 (4)
C22B0.073 (3)0.060 (3)0.053 (3)0.021 (3)0.011 (3)0.003 (3)
C23B0.079 (4)0.070 (4)0.062 (4)0.018 (4)0.012 (4)0.006 (4)
C24B0.087 (5)0.066 (4)0.061 (4)0.022 (4)0.008 (4)0.012 (4)
C25B0.092 (4)0.060 (4)0.061 (4)0.020 (4)0.000 (4)0.011 (4)
C26B0.067 (4)0.051 (4)0.041 (4)0.018 (4)0.007 (4)0.002 (4)
C27B0.081 (4)0.053 (4)0.048 (4)0.017 (4)0.001 (4)0.010 (4)
C28B0.086 (6)0.054 (6)0.058 (6)0.008 (6)0.002 (6)0.008 (5)
Geometric parameters (Å, º) top
I1—C12.093 (4)C15B—C16B1.439 (9)
I2—C82.089 (4)C18—C191.440 (6)
N3—C191.138 (5)C18—C201.442 (5)
N4—C201.137 (5)C21—C28i1.290 (18)
C1—C21.380 (5)C21—C221.48 (2)
C1—C141.387 (5)C21—H210.9300
C2—C31.377 (6)C22—C231.384 (13)
C2—H2A0.9300C22—C261.423 (11)
C3—C41.393 (5)C23—C241.329 (14)
C3—H3A0.9300C23—H230.9300
C4—C131.409 (5)C24—C251.317 (13)
C4—C51.472 (5)C24—H240.9300
C5—C15B1.362 (8)C25—C271.461 (12)
C5—C151.362 (7)C25—H250.9300
C5—C61.472 (5)C26—C271.409 (10)
C6—C71.391 (5)C26—C26i1.431 (15)
C6—C111.413 (5)C27—C281.411 (14)
C7—C81.386 (6)C28—C21i1.290 (18)
C7—H7A0.9300C28—H280.9300
C8—C91.382 (6)C21B—C28Bi1.23 (4)
C9—C101.374 (6)C21B—C22B1.48 (2)
C9—H9A0.9300C21B—H21B0.9300
C10—C111.390 (5)C22B—C23B1.395 (15)
C10—H10A0.9300C22B—C26B1.425 (12)
C11—C121.464 (5)C23B—C24B1.336 (15)
C12—C181.355 (5)C23B—H23B0.9300
C12—C131.477 (5)C24B—C25B1.290 (14)
C13—C141.387 (5)C24B—H24B0.9300
C14—H14A0.9300C25B—C27B1.456 (14)
N1—C161.135 (8)C25B—H25B0.9300
N2—C171.151 (8)C26B—C27B1.408 (12)
C15—C171.437 (9)C26B—C26Bi1.42 (2)
C15—C161.439 (8)C27B—C28B1.420 (16)
N1B—C16B1.137 (9)C28B—C21Bi1.23 (4)
N2B—C17B1.151 (9)C28B—H28B0.9300
C15B—C17B1.436 (10)
C2—C1—C14120.4 (3)C12—C18—C19123.2 (3)
C2—C1—I1120.4 (3)C12—C18—C20123.9 (3)
C14—C1—I1119.2 (3)C19—C18—C20112.5 (3)
C3—C2—C1119.8 (3)N3—C19—C18176.0 (4)
C3—C2—H2A120.1N4—C20—C18176.8 (4)
C1—C2—H2A120.1C28i—C21—C22123.2 (12)
C2—C3—C4121.3 (3)C28i—C21—H21118.4
C2—C3—H3A119.4C22—C21—H21118.4
C4—C3—H3A119.4C23—C22—C26119.4 (10)
C3—C4—C13118.4 (3)C23—C22—C21124.3 (9)
C3—C4—C5123.8 (3)C26—C22—C21116.2 (8)
C13—C4—C5117.7 (3)C24—C23—C22119.4 (9)
C15B—C5—C6118.7 (11)C24—C23—H23120.3
C15—C5—C6124.7 (7)C22—C23—H23120.3
C15B—C5—C4126.8 (11)C25—C24—C23125.5 (9)
C15—C5—C4120.8 (7)C25—C24—H24117.2
C6—C5—C4114.5 (3)C23—C24—H24117.2
C7—C6—C11119.5 (4)C24—C25—C27118.9 (9)
C7—C6—C5122.5 (3)C24—C25—H25120.5
C11—C6—C5118.0 (3)C27—C25—H25120.5
C8—C7—C6119.5 (4)C27—C26—C22119.8 (7)
C8—C7—H7A120.3C27—C26—C26i121.4 (9)
C6—C7—H7A120.3C22—C26—C26i118.8 (10)
C9—C8—C7121.4 (4)C26—C27—C28118.4 (8)
C9—C8—I2118.0 (3)C26—C27—C25116.8 (8)
C7—C8—I2120.6 (3)C28—C27—C25124.8 (7)
C10—C9—C8119.4 (4)C21i—C28—C27122.0 (12)
C10—C9—H9A120.3C21i—C28—H28119.0
C8—C9—H9A120.3C27—C28—H28119.0
C9—C10—C11121.0 (4)C28Bi—C21B—C22B124.6 (18)
C9—C10—H10A119.5C28Bi—C21B—H21B117.7
C11—C10—H10A119.5C22B—C21B—H21B117.7
C10—C11—C6119.3 (3)C23B—C22B—C26B118.4 (12)
C10—C11—C12122.7 (3)C23B—C22B—C21B127.1 (11)
C6—C11—C12117.9 (3)C26B—C22B—C21B114.5 (12)
C18—C12—C11123.4 (3)C24B—C23B—C22B118.9 (12)
C18—C12—C13122.2 (3)C24B—C23B—H23B120.5
C11—C12—C13114.4 (3)C22B—C23B—H23B120.5
C14—C13—C4120.0 (3)C25B—C24B—C23B126.7 (13)
C14—C13—C12121.9 (3)C25B—C24B—H24B116.7
C4—C13—C12118.0 (3)C23B—C24B—H24B116.7
C1—C14—C13120.0 (3)C24B—C25B—C27B118.7 (11)
C1—C14—H14A120.0C24B—C25B—H25B120.6
C13—C14—H14A120.0C27B—C25B—H25B120.6
C5—C15—C17123.2 (10)C27B—C26B—C26Bi119.2 (13)
C5—C15—C16124.4 (11)C27B—C26B—C22B120.1 (10)
C17—C15—C16112.1 (7)C26Bi—C26B—C22B120.6 (13)
N1—C16—C15179.6 (15)C26B—C27B—C28B118.6 (13)
N2—C17—C15175.7 (12)C26B—C27B—C25B117.1 (11)
C5—C15B—C17B125.7 (16)C28B—C27B—C25B124.3 (13)
C5—C15B—C16B122.1 (17)C21Bi—C28B—C27B122 (2)
C17B—C15B—C16B112.1 (10)C21Bi—C28B—H28B118.8
N1B—C16B—C15B175 (2)C27B—C28B—H28B118.8
N2B—C17B—C15B175 (2)
C14—C1—C2—C32.4 (6)C4—C5—C15—C17169.1 (18)
I1—C1—C2—C3175.6 (3)C6—C5—C15—C16179.2 (15)
C1—C2—C3—C41.2 (6)C4—C5—C15—C163 (3)
C2—C3—C4—C131.1 (5)C6—C5—C15B—C17B0 (6)
C2—C3—C4—C5176.8 (4)C4—C5—C15B—C17B179 (3)
C3—C4—C5—C15B34 (3)C6—C5—C15B—C16B177 (3)
C13—C4—C5—C15B148 (3)C4—C5—C15B—C16B2 (6)
C3—C4—C5—C1538 (2)C11—C12—C18—C19174.0 (3)
C13—C4—C5—C15144 (2)C13—C12—C18—C193.6 (5)
C3—C4—C5—C6144.9 (3)C11—C12—C18—C201.9 (6)
C13—C4—C5—C633.1 (4)C13—C12—C18—C20175.6 (3)
C15B—C5—C6—C738 (3)C28i—C21—C22—C23179 (2)
C15—C5—C6—C743 (2)C28i—C21—C22—C260 (4)
C4—C5—C6—C7140.8 (3)C26—C22—C23—C241.4 (13)
C15B—C5—C6—C11145 (3)C21—C22—C23—C24180 (2)
C15—C5—C6—C11141 (2)C22—C23—C24—C251.6 (14)
C4—C5—C6—C1135.7 (4)C23—C24—C25—C274.0 (14)
C11—C6—C7—C80.2 (5)C23—C22—C26—C271.7 (15)
C5—C6—C7—C8176.7 (3)C21—C22—C26—C27179 (2)
C6—C7—C8—C91.8 (6)C23—C22—C26—C26i180.0 (12)
C6—C7—C8—I2175.8 (3)C21—C22—C26—C26i1 (3)
C7—C8—C9—C102.0 (6)C22—C26—C27—C28179.9 (9)
I2—C8—C9—C10175.7 (3)C26i—C26—C27—C281.7 (19)
C8—C9—C10—C110.0 (6)C22—C26—C27—C250.6 (14)
C9—C10—C11—C62.1 (5)C26i—C26—C27—C25177.7 (13)
C9—C10—C11—C12174.4 (4)C24—C25—C27—C263.3 (13)
C7—C6—C11—C102.2 (5)C24—C25—C27—C28177.4 (8)
C5—C6—C11—C10178.8 (3)C26—C27—C28—C21i1 (3)
C7—C6—C11—C12174.5 (3)C25—C27—C28—C21i178 (2)
C5—C6—C11—C122.2 (5)C28Bi—C21B—C22B—C23B176 (5)
C10—C11—C12—C1839.3 (5)C28Bi—C21B—C22B—C26B3 (5)
C6—C11—C12—C18144.2 (3)C26B—C22B—C23B—C24B0 (3)
C10—C11—C12—C13143.1 (3)C21B—C22B—C23B—C24B178.9 (15)
C6—C11—C12—C1333.5 (4)C22B—C23B—C24B—C25B2 (3)
C3—C4—C13—C142.4 (5)C23B—C24B—C25B—C27B1 (3)
C5—C4—C13—C14175.7 (3)C23B—C22B—C26B—C27B2 (3)
C3—C4—C13—C12179.4 (3)C21B—C22B—C26B—C27B178.4 (18)
C5—C4—C13—C122.6 (5)C23B—C22B—C26B—C26Bi180 (3)
C18—C12—C13—C1440.1 (5)C21B—C22B—C26B—C26Bi1 (3)
C11—C12—C13—C14142.2 (3)C26Bi—C26B—C27B—C28B1 (5)
C18—C12—C13—C4141.7 (3)C22B—C26B—C27B—C28B178 (4)
C11—C12—C13—C436.1 (4)C26Bi—C26B—C27B—C25B179 (2)
C2—C1—C14—C131.1 (6)C22B—C26B—C27B—C25B3 (3)
I1—C1—C14—C13176.8 (3)C24B—C25B—C27B—C26B2 (2)
C4—C13—C14—C11.2 (5)C24B—C25B—C27B—C28B180 (4)
C12—C13—C14—C1179.5 (3)C26B—C27B—C28B—C21Bi3 (9)
C6—C5—C15—C177 (4)C25B—C27B—C28B—C21Bi176 (5)
Symmetry code: (i) x+2, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···I1ii0.933.244.144 (4)164
C9—H9···N2iii0.932.603.443 (17)150
C9—H9···N2Biii0.932.623.38 (3)139
Symmetry codes: (ii) x+1, y, z; (iii) x+1, y+1, z+1.
(III) 11,11,12,12-Tetracyano-2,6-diiodo-9,10-anthraquinodimethane–tetrathiafulvalene (2/1) top
Crystal data top
C20H6I2N4·0.5C6H4S4Z = 2
Mr = 658.25F(000) = 624
Triclinic, P1Dx = 1.936 Mg m3
a = 8.615 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.631 (3) ÅCell parameters from 9509 reflections
c = 12.450 (3) Åθ = 2.6–27.2°
α = 80.247 (9)°µ = 2.99 mm1
β = 74.695 (9)°T = 273 K
γ = 70.392 (8)°Prism, black
V = 1129.0 (5) Å30.46 × 0.27 × 0.12 mm
Data collection top
Bruker D8 Venture/Photon 100
diffractometer
4993 independent reflections
Radiation source: microfocus sealed tube4572 reflections with I > 2σ(I)
Multilayer mirrors monochromatorRint = 0.027
profile data from φ and ω scansθmax = 27.2°, θmin = 2.4°
Absorption correction: integration
(SADABS; Bruker, 2014)
h = 1111
Tmin = 0.926, Tmax = 0.978k = 1414
29346 measured reflectionsl = 1515
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041 w = 1/[σ2(Fo2) + (0.0457P)2 + 2.8841P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.104(Δ/σ)max = 0.002
S = 1.04Δρmax = 1.71 e Å3
4993 reflectionsΔρmin = 1.20 e Å3
281 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0373 (11)
Special details top

Experimental. One distinct cell was identified using APEX2 (Bruker, 2014). Seven frame series were integrated and filtered for statistical outliers using SAINT (Bruker, 2013) then corrected for absorption by integration using SAINT/SADABS v2014/2 (Bruker, 2014) to sort, merge, and scale the combined data. No decay correction was applied.

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. Structure was phased by direct methods (Sheldrick, 2014). Systematic conditions suggested the ambiguous space group. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F2. The highest peaks in the final difference Fourier map were in the vicinity of the I atoms; the final map had no other significant features. A final analysis of variance between observed and calculated structure factors showed little dependence on amplitude and resolution.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.79542 (4)1.18759 (3)0.96735 (3)0.05333 (13)
I21.25872 (5)0.29582 (3)0.57238 (3)0.07177 (15)
N11.2833 (7)1.0080 (5)0.4452 (4)0.0795 (14)
N21.2746 (7)0.6866 (5)0.3438 (4)0.0766 (14)
N30.4216 (5)1.0444 (4)0.8397 (5)0.0657 (12)
N40.4563 (5)0.7109 (4)0.7340 (4)0.0601 (10)
C10.9011 (5)1.0500 (3)0.8589 (3)0.0388 (8)
C21.0566 (5)1.0435 (4)0.7869 (4)0.0421 (8)
H21.11321.09800.79000.051*
C31.1270 (5)0.9564 (4)0.7110 (3)0.0401 (8)
H31.23320.95050.66500.048*
C41.0414 (4)0.8766 (3)0.7020 (3)0.0350 (7)
C51.1037 (4)0.7892 (3)0.6161 (3)0.0360 (7)
C61.0562 (5)0.6759 (3)0.6477 (3)0.0370 (7)
C71.1595 (5)0.5644 (4)0.6067 (3)0.0437 (9)
H71.26250.55980.55680.052*
C81.1085 (6)0.4604 (4)0.6402 (4)0.0461 (9)
C90.9592 (6)0.4636 (4)0.7182 (4)0.0454 (9)
H90.92780.39270.74200.054*
C100.8578 (5)0.5732 (4)0.7600 (3)0.0400 (8)
H100.75790.57570.81280.048*
C110.9022 (4)0.6802 (3)0.7246 (3)0.0350 (7)
C120.7950 (4)0.7993 (3)0.7659 (3)0.0329 (7)
C130.8846 (4)0.8827 (3)0.7772 (3)0.0331 (7)
C140.8180 (5)0.9676 (3)0.8569 (3)0.0368 (7)
H140.71760.96890.90870.044*
C151.1941 (5)0.8135 (4)0.5111 (3)0.0423 (8)
C161.2413 (6)0.9236 (4)0.4769 (4)0.0516 (10)
C171.2375 (6)0.7395 (5)0.4204 (4)0.0549 (11)
C180.6243 (4)0.8335 (3)0.7830 (3)0.0362 (7)
C190.5145 (5)0.9524 (4)0.8147 (4)0.0447 (9)
C200.5350 (5)0.7613 (4)0.7567 (4)0.0432 (9)
S10.20489 (15)0.56951 (10)0.90038 (10)0.0505 (3)
S20.17172 (15)0.32114 (10)0.94620 (10)0.0509 (3)
C210.0782 (5)0.4771 (4)0.9691 (3)0.0416 (8)
C220.3719 (6)0.4506 (4)0.8411 (5)0.0583 (12)
H220.46950.46480.79570.070*
C230.3572 (5)0.3372 (4)0.8623 (4)0.0558 (11)
H230.44410.27010.83270.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0614 (2)0.04952 (18)0.05221 (19)0.01940 (14)0.00738 (13)0.01638 (13)
I20.0840 (3)0.0458 (2)0.0699 (2)0.00116 (16)0.00381 (19)0.02337 (15)
N10.101 (4)0.083 (3)0.053 (3)0.045 (3)0.006 (2)0.013 (2)
N20.077 (3)0.104 (4)0.050 (2)0.039 (3)0.009 (2)0.025 (2)
N30.0398 (19)0.049 (2)0.107 (4)0.0096 (17)0.007 (2)0.025 (2)
N40.0417 (19)0.052 (2)0.091 (3)0.0185 (17)0.012 (2)0.016 (2)
C10.0401 (19)0.0373 (18)0.0399 (19)0.0118 (15)0.0090 (15)0.0057 (15)
C20.0399 (19)0.042 (2)0.049 (2)0.0189 (16)0.0117 (17)0.0022 (17)
C30.0312 (17)0.046 (2)0.043 (2)0.0158 (15)0.0047 (15)0.0003 (16)
C40.0299 (16)0.0368 (18)0.0361 (18)0.0099 (14)0.0064 (14)0.0008 (14)
C50.0267 (16)0.0402 (18)0.0367 (18)0.0071 (14)0.0055 (13)0.0007 (14)
C60.0333 (17)0.0413 (19)0.0341 (17)0.0093 (14)0.0052 (14)0.0054 (14)
C70.040 (2)0.045 (2)0.039 (2)0.0038 (16)0.0035 (16)0.0100 (16)
C80.054 (2)0.0353 (19)0.044 (2)0.0019 (17)0.0115 (18)0.0129 (16)
C90.051 (2)0.0365 (19)0.049 (2)0.0120 (17)0.0135 (18)0.0050 (16)
C100.0392 (19)0.0398 (19)0.0408 (19)0.0128 (15)0.0086 (16)0.0016 (15)
C110.0321 (17)0.0356 (17)0.0352 (17)0.0078 (14)0.0072 (14)0.0035 (14)
C120.0332 (17)0.0350 (17)0.0288 (16)0.0132 (14)0.0015 (13)0.0008 (13)
C130.0304 (16)0.0334 (17)0.0345 (17)0.0103 (13)0.0054 (13)0.0019 (13)
C140.0324 (17)0.0382 (18)0.0374 (18)0.0116 (14)0.0034 (14)0.0022 (14)
C150.0329 (18)0.049 (2)0.0389 (19)0.0105 (16)0.0014 (15)0.0026 (16)
C160.051 (2)0.057 (3)0.039 (2)0.017 (2)0.0002 (18)0.0036 (19)
C170.046 (2)0.074 (3)0.041 (2)0.023 (2)0.0038 (18)0.007 (2)
C180.0307 (17)0.0342 (17)0.0401 (19)0.0114 (14)0.0002 (14)0.0029 (14)
C190.0301 (18)0.042 (2)0.060 (2)0.0124 (16)0.0030 (17)0.0078 (18)
C200.0315 (18)0.040 (2)0.052 (2)0.0095 (15)0.0001 (16)0.0064 (17)
S10.0518 (6)0.0407 (5)0.0554 (6)0.0149 (4)0.0014 (5)0.0143 (4)
S20.0518 (6)0.0380 (5)0.0569 (6)0.0120 (4)0.0028 (5)0.0071 (4)
C210.044 (2)0.0396 (19)0.0395 (19)0.0117 (16)0.0059 (16)0.0065 (15)
C220.041 (2)0.052 (3)0.080 (3)0.0157 (19)0.000 (2)0.019 (2)
C230.036 (2)0.051 (2)0.075 (3)0.0045 (18)0.003 (2)0.026 (2)
Geometric parameters (Å, º) top
I1—C12.079 (4)C9—C101.377 (6)
I2—C82.088 (4)C9—H90.9300
N1—C161.132 (7)C10—C111.390 (5)
N2—C171.139 (6)C10—H100.9300
N3—C191.135 (6)C11—C121.473 (5)
N4—C201.143 (6)C12—C181.355 (5)
C1—C141.381 (5)C12—C131.470 (5)
C1—C21.387 (6)C13—C141.393 (5)
C2—C31.378 (6)C14—H140.9300
C2—H20.9300C15—C171.430 (6)
C3—C41.398 (5)C15—C161.435 (6)
C3—H30.9300C18—C201.437 (5)
C4—C131.413 (5)C18—C191.440 (5)
C4—C51.471 (5)S1—C221.725 (5)
C5—C151.371 (5)S1—C211.750 (4)
C5—C61.470 (5)S2—C231.712 (5)
C6—C71.395 (5)S2—C211.759 (4)
C6—C111.408 (5)C21—C21i1.342 (8)
C7—C81.385 (6)C22—C231.343 (7)
C7—H70.9300C22—H220.9300
C8—C91.386 (6)C23—H230.9300
C14—C1—C2120.5 (4)C6—C11—C12117.9 (3)
C14—C1—I1121.1 (3)C18—C12—C13122.2 (3)
C2—C1—I1118.5 (3)C18—C12—C11121.5 (3)
C3—C2—C1119.9 (4)C13—C12—C11116.0 (3)
C3—C2—H2120.1C14—C13—C4120.0 (3)
C1—C2—H2120.1C14—C13—C12122.2 (3)
C2—C3—C4121.1 (3)C4—C13—C12117.8 (3)
C2—C3—H3119.5C1—C14—C13120.0 (3)
C4—C3—H3119.5C1—C14—H14120.0
C3—C4—C13118.4 (3)C13—C14—H14120.0
C3—C4—C5123.3 (3)C5—C15—C17124.5 (4)
C13—C4—C5118.3 (3)C5—C15—C16123.2 (4)
C15—C5—C6121.6 (4)C17—C15—C16112.1 (4)
C15—C5—C4122.5 (4)N1—C16—C15176.7 (5)
C6—C5—C4115.8 (3)N2—C17—C15175.6 (6)
C7—C6—C11119.0 (4)C12—C18—C20123.4 (3)
C7—C6—C5122.6 (3)C12—C18—C19123.8 (3)
C11—C6—C5118.4 (3)C20—C18—C19112.3 (3)
C8—C7—C6120.0 (4)N3—C19—C18176.8 (4)
C8—C7—H7120.0N4—C20—C18175.5 (4)
C6—C7—H7120.0C22—S1—C2194.9 (2)
C7—C8—C9121.1 (4)C23—S2—C2195.6 (2)
C7—C8—I2119.6 (3)C21i—C21—S1122.4 (4)
C9—C8—I2119.3 (3)C21i—C21—S2123.5 (4)
C10—C9—C8119.1 (4)S1—C21—S2114.0 (2)
C10—C9—H9120.5C23—C22—S1118.3 (4)
C8—C9—H9120.5C23—C22—H22120.9
C9—C10—C11121.2 (4)S1—C22—H22120.9
C9—C10—H10119.4C22—C23—S2117.2 (3)
C11—C10—H10119.4C22—C23—H23121.4
C10—C11—C6119.6 (3)S2—C23—H23121.4
C10—C11—C12122.6 (3)
C14—C1—C2—C31.6 (6)C6—C11—C12—C1332.9 (5)
I1—C1—C2—C3177.5 (3)C3—C4—C13—C140.8 (5)
C1—C2—C3—C42.5 (6)C5—C4—C13—C14177.4 (3)
C2—C3—C4—C133.6 (6)C3—C4—C13—C12179.3 (3)
C2—C3—C4—C5174.5 (4)C5—C4—C13—C121.1 (5)
C3—C4—C5—C1532.7 (6)C18—C12—C13—C1435.1 (5)
C13—C4—C5—C15145.4 (4)C11—C12—C13—C14150.3 (3)
C3—C4—C5—C6150.1 (4)C18—C12—C13—C4143.3 (4)
C13—C4—C5—C631.8 (5)C11—C12—C13—C431.2 (5)
C15—C5—C6—C734.5 (6)C2—C1—C14—C134.4 (6)
C4—C5—C6—C7148.3 (4)I1—C1—C14—C13174.7 (3)
C15—C5—C6—C11147.0 (4)C4—C13—C14—C13.2 (5)
C4—C5—C6—C1130.2 (5)C12—C13—C14—C1175.3 (3)
C11—C6—C7—C81.1 (6)C6—C5—C15—C175.9 (6)
C5—C6—C7—C8179.5 (4)C4—C5—C15—C17171.1 (4)
C6—C7—C8—C92.9 (6)C6—C5—C15—C16179.4 (4)
C6—C7—C8—I2177.1 (3)C4—C5—C15—C162.4 (6)
C7—C8—C9—C102.1 (6)C13—C12—C18—C20170.4 (3)
I2—C8—C9—C10177.9 (3)C11—C12—C18—C203.9 (6)
C8—C9—C10—C110.5 (6)C13—C12—C18—C190.6 (6)
C9—C10—C11—C62.3 (6)C11—C12—C18—C19174.9 (4)
C9—C10—C11—C12178.7 (4)C22—S1—C21—C21i178.8 (5)
C7—C6—C11—C101.5 (5)C22—S1—C21—S20.5 (3)
C5—C6—C11—C10177.0 (3)C23—S2—C21—C21i179.0 (5)
C7—C6—C11—C12179.5 (3)C23—S2—C21—S10.7 (3)
C5—C6—C11—C122.0 (5)C21—S1—C22—C230.0 (5)
C10—C11—C12—C1839.3 (5)S1—C22—C23—S20.5 (6)
C6—C11—C12—C18141.7 (4)C21—S2—C23—C220.7 (5)
C10—C11—C12—C13146.1 (4)
Symmetry code: (i) x, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···N3ii0.932.683.310 (6)126
Symmetry code: (ii) x, y1, z.
Selected dihedral angles (°) [Please provide s.u. values] top
The dihedral angles formed by the mean plane defined by atoms C4/C6/C11/C13 and the mean plane defined by the atoms in the table.
C6–C11C1–C4/C13/C14
DITCAQ21.00119.546
(I)21.44519.462
(II)21.82019.750
(III)16.56912.834
 

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