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), C
20H
6I
2N
4, and its charge-transfer complexes with various electron donors, namely DITCAQ-anthracene (2/1), C
20H
6I
2N
4·0.5C
14H
10, (I), DITCAQ-pyrene (2/1), C
20H
6I
2N
4·0.5C
16H
10, (II), and DITCAQ-tetrathiafulvalene (2/1), C
20H
6I
2N
4·0.5C
6H
4S
4, (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.
-
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
CCDC references: 1509828; 1509827; 1509826; 1509825
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
C20H6I2N4 | Dx = 2.083 Mg m−3 |
Mr = 556.09 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 9591 reflections |
a = 8.7660 (3) Å | θ = 2.5–27.1° |
b = 12.2655 (4) Å | µ = 3.56 mm−1 |
c = 16.4903 (6) Å | T = 100 K |
V = 1773.03 (11) Å3 | Prism, yellow |
Z = 4 | 0.22 × 0.19 × 0.10 mm |
F(000) = 1040 | |
Data collection top
Bruker D8 Venture/Photon 100 diffractometer | 3929 independent reflections |
Radiation source: microfocus sealed tube | 3849 reflections with I > 2σ(I) |
Multilayer mirrors monochromator | Rint = 0.032 |
profile data from φ and ω scans | θmax = 27.2°, θmin = 2.5° |
Absorption correction: integration (SADABS; Bruker, 2014) | h = −11→11 |
Tmin = 0.999, Tmax = 1.000 | k = −15→15 |
20684 measured reflections | l = −21→21 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-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 = 1.17 | Δρmax = 0.32 e Å−3 |
3929 reflections | Δρmin = −0.82 e Å−3 |
235 parameters | Absolute structure: Flack (1983), with 1893 Friedel pairs |
1 restraint | Absolute 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 | x | y | z | Uiso*/Ueq | |
I1 | 0.61913 (3) | 0.27014 (2) | 0.38906 (2) | 0.01539 (7) | |
I2 | 0.42334 (4) | 1.10665 (2) | 0.58154 (2) | 0.01841 (8) | |
N1 | 0.2046 (5) | 0.4920 (3) | 0.7375 (3) | 0.0237 (10) | |
N2 | 0.0777 (5) | 0.8249 (3) | 0.7036 (3) | 0.0165 (8) | |
N3 | 0.1475 (5) | 0.4509 (3) | 0.2769 (3) | 0.0169 (8) | |
N4 | 0.0564 (5) | 0.7875 (3) | 0.2597 (3) | 0.0189 (9) | |
C1 | 0.5113 (5) | 0.3973 (3) | 0.4514 (3) | 0.0115 (8) | |
C2 | 0.5116 (5) | 0.3992 (3) | 0.5355 (3) | 0.0129 (9) | |
H2 | 0.5578 | 0.3412 | 0.5648 | 0.016* | |
C3 | 0.4448 (4) | 0.4851 (3) | 0.5772 (4) | 0.0118 (8) | |
H3 | 0.4473 | 0.4865 | 0.6348 | 0.014* | |
C4 | 0.3742 (5) | 0.5694 (4) | 0.5348 (3) | 0.0102 (8) | |
C5 | 0.3056 (5) | 0.6652 (3) | 0.5746 (3) | 0.0089 (7) | |
C6 | 0.3227 (5) | 0.7678 (3) | 0.5289 (3) | 0.0094 (8) | |
C7 | 0.3530 (5) | 0.8668 (3) | 0.5683 (3) | 0.0104 (8) | |
H7 | 0.3606 | 0.8696 | 0.6257 | 0.013* | |
C8 | 0.3719 (5) | 0.9610 (3) | 0.5220 (3) | 0.0115 (8) | |
C9 | 0.3597 (5) | 0.9587 (4) | 0.4374 (3) | 0.0125 (9) | |
H9 | 0.3714 | 1.0236 | 0.4066 | 0.015* | |
C10 | 0.3301 (5) | 0.8601 (3) | 0.3991 (3) | 0.0109 (8) | |
H10 | 0.3208 | 0.8580 | 0.3417 | 0.013* | |
C11 | 0.3139 (5) | 0.7638 (3) | 0.4439 (3) | 0.0100 (8) | |
C12 | 0.2931 (5) | 0.6562 (3) | 0.4056 (2) | 0.0100 (9) | |
C13 | 0.3704 (5) | 0.5654 (3) | 0.4487 (3) | 0.0104 (8) | |
C14 | 0.4406 (5) | 0.4798 (3) | 0.4077 (3) | 0.0117 (9) | |
H14 | 0.4401 | 0.4779 | 0.3501 | 0.014* | |
C15 | 0.2304 (5) | 0.6617 (4) | 0.6468 (3) | 0.0108 (8) | |
C16 | 0.2175 (5) | 0.5652 (4) | 0.6960 (3) | 0.0144 (9) | |
C17 | 0.1492 (5) | 0.7539 (3) | 0.6787 (3) | 0.0109 (9) | |
C18 | 0.2083 (5) | 0.6402 (3) | 0.3378 (3) | 0.0111 (8) | |
C19 | 0.1785 (5) | 0.5331 (3) | 0.3045 (3) | 0.0124 (9) | |
C20 | 0.1273 (5) | 0.7251 (4) | 0.2954 (3) | 0.0128 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.01862 (14) | 0.01209 (12) | 0.01547 (13) | 0.00485 (10) | 0.00099 (13) | −0.00148 (13) |
I2 | 0.02827 (16) | 0.01149 (13) | 0.01547 (14) | −0.00567 (11) | −0.00333 (14) | 0.00102 (12) |
N1 | 0.027 (2) | 0.020 (2) | 0.024 (2) | 0.0023 (17) | 0.0077 (19) | 0.0104 (18) |
N2 | 0.017 (2) | 0.020 (2) | 0.013 (2) | 0.0014 (15) | 0.0006 (16) | 0.0019 (16) |
N3 | 0.020 (2) | 0.017 (2) | 0.0134 (19) | 0.0017 (15) | −0.0024 (16) | −0.0006 (16) |
N4 | 0.020 (2) | 0.019 (2) | 0.018 (2) | −0.0005 (16) | −0.0038 (17) | 0.0033 (16) |
C1 | 0.013 (2) | 0.0088 (19) | 0.013 (2) | −0.0010 (15) | 0.0013 (17) | −0.0020 (15) |
C2 | 0.014 (2) | 0.0091 (19) | 0.016 (2) | −0.0002 (16) | −0.0028 (17) | 0.0029 (15) |
C3 | 0.012 (2) | 0.0110 (17) | 0.0125 (19) | −0.0020 (15) | 0.001 (2) | 0.0053 (19) |
C4 | 0.012 (2) | 0.009 (2) | 0.009 (2) | −0.0006 (15) | 0.0032 (16) | 0.0009 (15) |
C5 | 0.0103 (19) | 0.0100 (17) | 0.0066 (18) | −0.0018 (14) | −0.0015 (18) | 0.0013 (16) |
C6 | 0.009 (2) | 0.0090 (19) | 0.010 (2) | 0.0006 (15) | 0.0002 (16) | 0.0032 (15) |
C7 | 0.014 (2) | 0.0086 (17) | 0.009 (2) | 0.0020 (15) | −0.0012 (16) | 0.0000 (15) |
C8 | 0.015 (2) | 0.008 (2) | 0.012 (2) | 0.0002 (15) | 0.0026 (17) | −0.0010 (16) |
C9 | 0.013 (2) | 0.011 (2) | 0.014 (2) | 0.0017 (16) | 0.0007 (17) | 0.0052 (16) |
C10 | 0.0133 (19) | 0.0120 (17) | 0.007 (2) | 0.0017 (15) | 0.0021 (17) | 0.0023 (17) |
C11 | 0.009 (2) | 0.0103 (19) | 0.010 (2) | 0.0027 (15) | 0.0025 (16) | −0.0006 (15) |
C12 | 0.011 (2) | 0.0111 (19) | 0.008 (2) | 0.0000 (14) | 0.0024 (15) | 0.0024 (15) |
C13 | 0.013 (2) | 0.011 (2) | 0.008 (2) | −0.0009 (16) | −0.0002 (16) | 0.0006 (15) |
C14 | 0.012 (2) | 0.0106 (18) | 0.013 (2) | −0.0008 (15) | 0.0009 (15) | 0.0003 (15) |
C15 | 0.013 (2) | 0.011 (2) | 0.009 (2) | 0.0014 (16) | −0.0022 (16) | 0.0018 (15) |
C16 | 0.013 (2) | 0.018 (2) | 0.013 (2) | 0.0015 (16) | 0.0036 (17) | 0.0009 (19) |
C17 | 0.011 (2) | 0.013 (2) | 0.008 (2) | −0.0043 (16) | −0.0007 (16) | 0.0024 (15) |
C18 | 0.013 (2) | 0.011 (2) | 0.009 (2) | 0.0010 (16) | 0.0037 (16) | 0.0010 (15) |
C19 | 0.012 (2) | 0.016 (2) | 0.009 (2) | 0.0024 (17) | 0.0011 (16) | 0.0019 (16) |
C20 | 0.017 (2) | 0.014 (2) | 0.007 (2) | 0.0001 (17) | 0.0004 (16) | −0.0011 (16) |
Geometric parameters (Å, º) top
I1—C1 | 2.094 (4) | C6—C11 | 1.405 (6) |
I2—C8 | 2.089 (4) | C7—C8 | 1.395 (6) |
N1—C16 | 1.135 (6) | C7—H7 | 0.9500 |
N2—C17 | 1.148 (6) | C8—C9 | 1.399 (6) |
N3—C19 | 1.139 (6) | C9—C10 | 1.388 (6) |
N4—C20 | 1.148 (6) | C9—H9 | 0.9500 |
C1—C2 | 1.386 (6) | C10—C11 | 1.402 (6) |
C1—C14 | 1.389 (6) | C10—H10 | 0.9500 |
C2—C3 | 1.388 (6) | C11—C12 | 1.473 (6) |
C2—H2 | 0.9500 | C12—C18 | 1.357 (6) |
C3—C4 | 1.393 (6) | C12—C13 | 1.485 (6) |
C3—H3 | 0.9500 | C13—C14 | 1.393 (6) |
C4—C13 | 1.420 (6) | C14—H14 | 0.9500 |
C4—C5 | 1.475 (6) | C15—C17 | 1.437 (6) |
C5—C15 | 1.361 (6) | C15—C16 | 1.439 (6) |
C5—C6 | 1.475 (5) | C18—C20 | 1.442 (6) |
C6—C7 | 1.402 (6) | C18—C19 | 1.448 (6) |
| | | |
C2—C1—C14 | 120.5 (4) | C8—C9—H9 | 120.5 |
C2—C1—I1 | 120.2 (3) | C9—C10—C11 | 120.9 (4) |
C14—C1—I1 | 119.3 (3) | C9—C10—H10 | 119.6 |
C1—C2—C3 | 120.5 (4) | C11—C10—H10 | 119.6 |
C1—C2—H2 | 119.7 | C10—C11—C6 | 119.4 (4) |
C3—C2—H2 | 119.7 | C10—C11—C12 | 122.8 (4) |
C2—C3—C4 | 120.1 (5) | C6—C11—C12 | 117.8 (4) |
C2—C3—H3 | 120.0 | C18—C12—C11 | 123.4 (4) |
C4—C3—H3 | 120.0 | C18—C12—C13 | 122.4 (4) |
C3—C4—C13 | 119.2 (4) | C11—C12—C13 | 114.2 (4) |
C3—C4—C5 | 123.2 (4) | C14—C13—C4 | 120.1 (4) |
C13—C4—C5 | 117.6 (4) | C14—C13—C12 | 122.3 (4) |
C15—C5—C4 | 124.2 (4) | C4—C13—C12 | 117.6 (4) |
C15—C5—C6 | 121.5 (4) | C1—C14—C13 | 119.6 (4) |
C4—C5—C6 | 114.3 (4) | C1—C14—H14 | 120.2 |
C7—C6—C11 | 120.2 (4) | C13—C14—H14 | 120.2 |
C7—C6—C5 | 121.4 (4) | C5—C15—C17 | 122.4 (4) |
C11—C6—C5 | 118.3 (4) | C5—C15—C16 | 123.8 (4) |
C8—C7—C6 | 119.1 (4) | C17—C15—C16 | 113.7 (4) |
C8—C7—H7 | 120.5 | N1—C16—C15 | 176.9 (5) |
C6—C7—H7 | 120.5 | N2—C17—C15 | 176.6 (5) |
C7—C8—C9 | 121.4 (4) | C12—C18—C20 | 124.4 (4) |
C7—C8—I2 | 118.5 (3) | C12—C18—C19 | 122.9 (4) |
C9—C8—I2 | 120.2 (3) | C20—C18—C19 | 112.5 (4) |
C10—C9—C8 | 119.0 (4) | N3—C19—C18 | 176.3 (5) |
C10—C9—H9 | 120.5 | N4—C20—C18 | 175.5 (5) |
| | | |
C14—C1—C2—C3 | −1.8 (7) | C5—C6—C11—C12 | −1.9 (6) |
I1—C1—C2—C3 | 177.8 (3) | C10—C11—C12—C18 | −37.7 (7) |
C1—C2—C3—C4 | 1.3 (7) | C6—C11—C12—C18 | 144.4 (4) |
C2—C3—C4—C13 | 0.6 (6) | C10—C11—C12—C13 | 143.6 (4) |
C2—C3—C4—C5 | −177.8 (4) | C6—C11—C12—C13 | −34.3 (6) |
C3—C4—C5—C15 | −36.5 (7) | C3—C4—C13—C14 | −1.9 (6) |
C13—C4—C5—C15 | 145.1 (4) | C5—C4—C13—C14 | 176.6 (4) |
C3—C4—C5—C6 | 144.3 (4) | C3—C4—C13—C12 | 179.5 (4) |
C13—C4—C5—C6 | −34.0 (6) | C5—C4—C13—C12 | −2.0 (6) |
C15—C5—C6—C7 | 39.8 (6) | C18—C12—C13—C14 | 39.1 (6) |
C4—C5—C6—C7 | −141.0 (4) | C11—C12—C13—C14 | −142.2 (4) |
C15—C5—C6—C11 | −142.7 (5) | C18—C12—C13—C4 | −142.4 (4) |
C4—C5—C6—C11 | 36.5 (6) | C11—C12—C13—C4 | 36.3 (5) |
C11—C6—C7—C8 | 1.0 (7) | C2—C1—C14—C13 | 0.5 (7) |
C5—C6—C7—C8 | 178.4 (4) | I1—C1—C14—C13 | −179.2 (3) |
C6—C7—C8—C9 | 0.6 (7) | C4—C13—C14—C1 | 1.4 (6) |
C6—C7—C8—I2 | −178.2 (3) | C12—C13—C14—C1 | 179.9 (4) |
C7—C8—C9—C10 | −0.9 (7) | C4—C5—C15—C17 | −172.1 (4) |
I2—C8—C9—C10 | 178.0 (3) | C6—C5—C15—C17 | 6.9 (7) |
C8—C9—C10—C11 | −0.5 (7) | C4—C5—C15—C16 | 4.4 (7) |
C9—C10—C11—C6 | 2.1 (7) | C6—C5—C15—C16 | −176.5 (4) |
C9—C10—C11—C12 | −175.7 (4) | C11—C12—C18—C20 | −0.6 (7) |
C7—C6—C11—C10 | −2.3 (7) | C13—C12—C18—C20 | 178.0 (4) |
C5—C6—C11—C10 | −179.9 (4) | C11—C12—C18—C19 | −174.8 (4) |
C7—C6—C11—C12 | 175.6 (4) | C13—C12—C18—C19 | 3.7 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···I2i | 0.95 | 3.12 | 3.748 (4) | 125 |
C7—H7···N3ii | 0.95 | 2.69 | 3.592 (6) | 160 |
Symmetry codes: (i) x, y−1, 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 = 645.20 | Dx = 1.825 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.7727 (9) Å | Cell parameters from 8277 reflections |
b = 8.5843 (5) Å | θ = 2.6–27.2° |
c = 20.5752 (13) Å | µ = 2.70 mm−1 |
β = 105.115 (3)° | T = 273 K |
V = 2348.4 (3) Å3 | Plate, orange |
Z = 4 | 0.22 × 0.21 × 0.08 mm |
Data collection top
Bruker Kappa APEXII CCD diffractometer | 5201 independent reflections |
Radiation source: fine-focus sealed tube | 4344 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
profile data from ω scans | θmax = 27.2°, θmin = 2.8° |
Absorption correction: integration (SADABS; Bruker, 2014) | h = −17→17 |
Tmin = 0.681, Tmax = 0.879 | k = −11→11 |
21378 measured reflections | l = −26→21 |
Refinement top
Refinement on F2 | 198 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.028 | H-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 reflections | Δρmax = 0.87 e Å−3 |
362 parameters | Δρmin = −0.92 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
I1 | 0.80023 (2) | −0.06182 (2) | 0.27495 (2) | 0.04243 (7) | |
I2 | 0.88708 (2) | −0.07183 (3) | 0.81408 (2) | 0.05564 (8) | |
N1 | 0.4533 (2) | −0.2878 (4) | 0.46726 (16) | 0.0570 (8) | |
N2 | 0.5193 (2) | −0.0972 (4) | 0.66344 (16) | 0.0587 (8) | |
N3 | 0.6795 (2) | 0.4264 (3) | 0.37357 (14) | 0.0514 (7) | |
N4 | 0.7651 (2) | 0.5770 (3) | 0.57558 (14) | 0.0457 (6) | |
C1 | 0.7533 (2) | −0.0610 (3) | 0.36362 (14) | 0.0319 (6) | |
C2 | 0.7029 (2) | −0.1914 (3) | 0.37856 (14) | 0.0358 (6) | |
H2A | 0.6886 | −0.2744 | 0.3486 | 0.043* | |
C3 | 0.6745 (2) | −0.1969 (3) | 0.43776 (14) | 0.0322 (6) | |
H3A | 0.6413 | −0.2847 | 0.4476 | 0.039* | |
C4 | 0.69455 (19) | −0.0733 (3) | 0.48342 (13) | 0.0268 (5) | |
C5 | 0.66956 (19) | −0.0753 (3) | 0.54877 (13) | 0.0270 (5) | |
C6 | 0.74263 (18) | 0.0061 (3) | 0.60332 (13) | 0.0274 (5) | |
C7 | 0.7695 (2) | −0.0525 (3) | 0.66834 (14) | 0.0338 (6) | |
H7A | 0.7392 | −0.1424 | 0.6789 | 0.041* | |
C8 | 0.8421 (2) | 0.0244 (4) | 0.71756 (14) | 0.0368 (6) | |
C9 | 0.8860 (2) | 0.1599 (3) | 0.70255 (14) | 0.0387 (6) | |
H9A | 0.9335 | 0.2116 | 0.7361 | 0.046* | |
C10 | 0.8594 (2) | 0.2183 (3) | 0.63781 (14) | 0.0335 (6) | |
H10A | 0.8887 | 0.3100 | 0.6281 | 0.040* | |
C11 | 0.78929 (18) | 0.1415 (3) | 0.58699 (12) | 0.0267 (5) | |
C12 | 0.76325 (18) | 0.1893 (3) | 0.51620 (12) | 0.0257 (5) | |
C13 | 0.74330 (18) | 0.0599 (3) | 0.46719 (13) | 0.0261 (5) | |
C14 | 0.77265 (19) | 0.0651 (3) | 0.40707 (13) | 0.0289 (5) | |
H14A | 0.8050 | 0.1527 | 0.3963 | 0.035* | |
C15 | 0.58413 (19) | −0.1388 (3) | 0.55841 (13) | 0.0302 (5) | |
C16 | 0.5121 (2) | −0.2219 (3) | 0.50680 (16) | 0.0378 (6) | |
C17 | 0.5517 (2) | −0.1170 (3) | 0.61862 (15) | 0.0378 (6) | |
C18 | 0.75180 (19) | 0.3408 (3) | 0.49645 (13) | 0.0284 (5) | |
C19 | 0.7134 (2) | 0.3856 (3) | 0.42720 (15) | 0.0339 (6) | |
C20 | 0.7616 (2) | 0.4700 (3) | 0.54249 (14) | 0.0321 (6) | |
C21 | 0.0347 (13) | 0.5813 (15) | 0.6384 (6) | 0.056 (2) | 0.64 (3) |
H21A | 0.0581 | 0.5070 | 0.6717 | 0.067* | 0.64 (3) |
C22 | 0.0138 (8) | 0.7271 (17) | 0.6548 (6) | 0.056 (2) | 0.64 (3) |
H22A | 0.0236 | 0.7538 | 0.6999 | 0.067* | 0.64 (3) |
C23 | −0.0229 (8) | 0.8398 (13) | 0.6045 (8) | 0.056 (2) | 0.64 (3) |
H23A | −0.0357 | 0.9403 | 0.6169 | 0.067* | 0.64 (3) |
C24 | −0.0399 (11) | 0.8040 (13) | 0.5380 (7) | 0.0518 (18) | 0.64 (3) |
H24A | −0.0641 | 0.8800 | 0.5056 | 0.062* | 0.64 (3) |
C25 | −0.021 (2) | 0.6496 (16) | 0.5176 (5) | 0.0454 (16) | 0.64 (3) |
C26 | −0.0409 (12) | 0.6062 (14) | 0.4505 (5) | 0.0456 (19) | 0.64 (3) |
H26A | −0.0691 | 0.6789 | 0.4175 | 0.055* | 0.64 (3) |
C27 | −0.0204 (18) | 0.4574 (16) | 0.4311 (8) | 0.042 (2) | 0.64 (3) |
C21B | 0.044 (2) | 0.539 (3) | 0.6403 (11) | 0.057 (3) | 0.36 (3) |
H21B | 0.0732 | 0.4591 | 0.6693 | 0.068* | 0.36 (3) |
C22B | 0.0259 (15) | 0.675 (3) | 0.6669 (10) | 0.060 (3) | 0.36 (3) |
H22B | 0.0391 | 0.6845 | 0.7134 | 0.072* | 0.36 (3) |
C23B | −0.0122 (14) | 0.805 (2) | 0.6262 (12) | 0.054 (3) | 0.36 (3) |
H23B | −0.0224 | 0.8986 | 0.6462 | 0.065* | 0.36 (3) |
C24B | −0.034 (2) | 0.795 (2) | 0.5578 (11) | 0.050 (3) | 0.36 (3) |
H24B | −0.0604 | 0.8803 | 0.5313 | 0.060* | 0.36 (3) |
C25B | −0.017 (4) | 0.651 (3) | 0.5271 (9) | 0.046 (2) | 0.36 (3) |
C26B | −0.033 (2) | 0.632 (3) | 0.4583 (10) | 0.043 (2) | 0.36 (3) |
H26B | −0.0532 | 0.7175 | 0.4303 | 0.052* | 0.36 (3) |
C27B | −0.020 (3) | 0.489 (3) | 0.4299 (14) | 0.042 (3) | 0.36 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.05931 (14) | 0.04209 (12) | 0.02975 (12) | −0.00404 (8) | 0.01848 (9) | −0.00580 (7) |
I2 | 0.05716 (15) | 0.07823 (18) | 0.02677 (12) | −0.00482 (11) | 0.00242 (9) | 0.01191 (9) |
N1 | 0.0429 (15) | 0.0708 (19) | 0.0576 (19) | −0.0154 (14) | 0.0139 (14) | −0.0189 (15) |
N2 | 0.0556 (18) | 0.078 (2) | 0.0482 (19) | 0.0041 (15) | 0.0231 (15) | 0.0130 (15) |
N3 | 0.081 (2) | 0.0377 (14) | 0.0370 (16) | 0.0103 (13) | 0.0181 (14) | 0.0064 (11) |
N4 | 0.0576 (17) | 0.0324 (13) | 0.0470 (16) | −0.0002 (11) | 0.0134 (13) | −0.0047 (11) |
C1 | 0.0389 (14) | 0.0324 (13) | 0.0255 (14) | 0.0057 (11) | 0.0103 (11) | 0.0009 (10) |
C2 | 0.0471 (16) | 0.0272 (13) | 0.0322 (15) | 0.0005 (11) | 0.0087 (12) | −0.0050 (11) |
C3 | 0.0384 (15) | 0.0237 (12) | 0.0342 (15) | −0.0001 (10) | 0.0091 (11) | 0.0022 (10) |
C4 | 0.0296 (13) | 0.0249 (12) | 0.0246 (13) | 0.0029 (9) | 0.0048 (10) | 0.0034 (9) |
C5 | 0.0296 (13) | 0.0224 (11) | 0.0280 (13) | 0.0027 (9) | 0.0055 (10) | 0.0045 (9) |
C6 | 0.0281 (13) | 0.0288 (12) | 0.0253 (13) | 0.0014 (10) | 0.0069 (10) | 0.0018 (10) |
C7 | 0.0358 (14) | 0.0376 (14) | 0.0281 (14) | 0.0009 (11) | 0.0087 (11) | 0.0057 (11) |
C8 | 0.0385 (15) | 0.0501 (17) | 0.0213 (14) | 0.0049 (12) | 0.0068 (11) | 0.0027 (11) |
C9 | 0.0373 (15) | 0.0478 (17) | 0.0291 (15) | −0.0014 (12) | 0.0053 (12) | −0.0085 (12) |
C10 | 0.0374 (14) | 0.0328 (14) | 0.0305 (14) | −0.0046 (11) | 0.0095 (11) | −0.0042 (11) |
C11 | 0.0279 (12) | 0.0274 (12) | 0.0244 (13) | 0.0029 (10) | 0.0062 (10) | 0.0002 (10) |
C12 | 0.0243 (12) | 0.0271 (12) | 0.0263 (13) | −0.0012 (9) | 0.0078 (10) | 0.0002 (10) |
C13 | 0.0274 (12) | 0.0250 (12) | 0.0257 (13) | 0.0029 (10) | 0.0064 (10) | 0.0016 (9) |
C14 | 0.0330 (13) | 0.0266 (12) | 0.0284 (14) | 0.0004 (10) | 0.0101 (11) | 0.0028 (10) |
C15 | 0.0317 (13) | 0.0273 (12) | 0.0305 (14) | 0.0005 (10) | 0.0060 (11) | 0.0053 (10) |
C16 | 0.0337 (15) | 0.0376 (15) | 0.0431 (17) | −0.0017 (12) | 0.0118 (13) | 0.0022 (13) |
C17 | 0.0345 (15) | 0.0410 (15) | 0.0380 (17) | −0.0011 (12) | 0.0093 (12) | 0.0092 (12) |
C18 | 0.0311 (13) | 0.0268 (12) | 0.0288 (13) | −0.0030 (10) | 0.0105 (10) | −0.0010 (10) |
C19 | 0.0477 (16) | 0.0225 (12) | 0.0347 (16) | 0.0017 (11) | 0.0163 (13) | 0.0024 (11) |
C20 | 0.0362 (14) | 0.0285 (13) | 0.0323 (15) | −0.0015 (10) | 0.0103 (11) | 0.0028 (11) |
C21 | 0.043 (4) | 0.057 (6) | 0.064 (4) | 0.002 (4) | 0.010 (3) | −0.002 (4) |
C22 | 0.044 (3) | 0.058 (5) | 0.064 (4) | 0.003 (4) | 0.010 (3) | −0.006 (4) |
C23 | 0.036 (3) | 0.056 (4) | 0.073 (5) | 0.007 (3) | 0.011 (3) | −0.007 (4) |
C24 | 0.034 (3) | 0.051 (3) | 0.069 (4) | 0.003 (2) | 0.011 (4) | −0.005 (3) |
C25 | 0.026 (3) | 0.042 (3) | 0.068 (4) | 0.001 (2) | 0.011 (4) | 0.001 (3) |
C26 | 0.030 (3) | 0.042 (4) | 0.061 (3) | −0.002 (3) | 0.005 (3) | 0.006 (3) |
C27 | 0.025 (3) | 0.039 (5) | 0.062 (3) | −0.004 (5) | 0.010 (2) | −0.002 (4) |
C21B | 0.035 (5) | 0.058 (7) | 0.070 (5) | 0.004 (6) | 0.002 (4) | −0.004 (5) |
C22B | 0.043 (4) | 0.061 (6) | 0.071 (5) | 0.003 (5) | 0.003 (4) | −0.007 (5) |
C23B | 0.039 (4) | 0.055 (5) | 0.068 (6) | 0.009 (4) | 0.011 (5) | −0.010 (4) |
C24B | 0.031 (4) | 0.049 (4) | 0.069 (6) | 0.006 (3) | 0.012 (5) | −0.008 (5) |
C25B | 0.028 (4) | 0.046 (4) | 0.066 (5) | −0.001 (4) | 0.013 (5) | −0.006 (4) |
C26B | 0.028 (4) | 0.035 (5) | 0.065 (4) | 0.001 (4) | 0.011 (4) | 0.000 (4) |
C27B | 0.028 (4) | 0.036 (7) | 0.060 (5) | −0.002 (6) | 0.009 (4) | 0.004 (5) |
Geometric parameters (Å, º) top
I1—C1 | 2.089 (3) | C18—C19 | 1.437 (4) |
I2—C8 | 2.090 (3) | C18—C20 | 1.442 (4) |
N1—C16 | 1.138 (4) | C21—C22 | 1.347 (8) |
N2—C17 | 1.137 (4) | C21—C27i | 1.43 (2) |
N3—C19 | 1.136 (4) | C21—H21A | 0.9300 |
N4—C20 | 1.137 (4) | C22—C23 | 1.411 (8) |
C1—C14 | 1.385 (4) | C22—H22A | 0.9300 |
C1—C2 | 1.392 (4) | C23—C24 | 1.361 (8) |
C2—C3 | 1.374 (4) | C23—H23A | 0.9300 |
C2—H2A | 0.9300 | C24—C25 | 1.435 (6) |
C3—C4 | 1.397 (4) | C24—H24A | 0.9300 |
C3—H3A | 0.9300 | C25—C26 | 1.385 (7) |
C4—C13 | 1.409 (3) | C25—C27i | 1.40 (2) |
C4—C5 | 1.472 (4) | C26—C27 | 1.389 (7) |
C5—C15 | 1.358 (3) | C26—H26A | 0.9300 |
C5—C6 | 1.474 (4) | C27—C25i | 1.40 (2) |
C6—C7 | 1.386 (4) | C27—C21i | 1.43 (2) |
C6—C11 | 1.410 (3) | C21B—C22B | 1.343 (10) |
C7—C8 | 1.390 (4) | C21B—C27Bi | 1.41 (4) |
C7—H7A | 0.9300 | C21B—H21B | 0.9300 |
C8—C9 | 1.383 (4) | C22B—C23B | 1.410 (10) |
C9—C10 | 1.380 (4) | C22B—H22B | 0.9300 |
C9—H9A | 0.9300 | C23B—C24B | 1.363 (10) |
C10—C11 | 1.390 (4) | C23B—H23B | 0.9300 |
C10—H10A | 0.9300 | C24B—C25B | 1.436 (8) |
C11—C12 | 1.465 (3) | C24B—H24B | 0.9300 |
C12—C18 | 1.359 (3) | C25B—C26B | 1.383 (9) |
C12—C13 | 1.477 (3) | C25B—C27Bi | 1.50 (4) |
C13—C14 | 1.399 (4) | C26B—C27B | 1.390 (9) |
C14—H14A | 0.9300 | C26B—H26B | 0.9300 |
C15—C17 | 1.435 (4) | C27B—C21Bi | 1.42 (4) |
C15—C16 | 1.439 (4) | C27B—C25Bi | 1.50 (4) |
| | | |
C14—C1—C2 | 120.6 (2) | C12—C18—C19 | 122.5 (2) |
C14—C1—I1 | 120.99 (19) | C12—C18—C20 | 123.8 (2) |
C2—C1—I1 | 118.40 (19) | C19—C18—C20 | 113.1 (2) |
C3—C2—C1 | 119.8 (2) | N3—C19—C18 | 176.2 (3) |
C3—C2—H2A | 120.1 | N4—C20—C18 | 175.6 (3) |
C1—C2—H2A | 120.1 | C22—C21—C27i | 118.9 (10) |
C2—C3—C4 | 121.2 (2) | C22—C21—H21A | 120.5 |
C2—C3—H3A | 119.4 | C27i—C21—H21A | 120.5 |
C4—C3—H3A | 119.4 | C21—C22—C23 | 120.8 (6) |
C3—C4—C13 | 118.7 (2) | C21—C22—H22A | 119.6 |
C3—C4—C5 | 123.6 (2) | C23—C22—H22A | 119.6 |
C13—C4—C5 | 117.7 (2) | C24—C23—C22 | 121.2 (6) |
C15—C5—C4 | 123.8 (2) | C24—C23—H23A | 119.4 |
C15—C5—C6 | 121.7 (2) | C22—C23—H23A | 119.4 |
C4—C5—C6 | 114.5 (2) | C23—C24—C25 | 120.4 (6) |
C7—C6—C11 | 120.4 (2) | C23—C24—H24A | 119.8 |
C7—C6—C5 | 121.4 (2) | C25—C24—H24A | 119.8 |
C11—C6—C5 | 118.2 (2) | C26—C25—C27i | 120.6 (10) |
C6—C7—C8 | 119.4 (2) | C26—C25—C24 | 122.4 (7) |
C6—C7—H7A | 120.3 | C27i—C25—C24 | 117.0 (9) |
C8—C7—H7A | 120.3 | C25—C26—C27 | 122.0 (7) |
C9—C8—C7 | 120.7 (3) | C25—C26—H26A | 119.0 |
C9—C8—I2 | 120.4 (2) | C27—C26—H26A | 119.0 |
C7—C8—I2 | 118.9 (2) | C26—C27—C25i | 117.3 (11) |
C10—C9—C8 | 120.0 (3) | C26—C27—C21i | 121.0 (11) |
C10—C9—H9A | 120.0 | C25i—C27—C21i | 121.5 (11) |
C8—C9—H9A | 120.0 | C22B—C21B—C27Bi | 123.2 (17) |
C9—C10—C11 | 120.7 (3) | C22B—C21B—H21B | 118.4 |
C9—C10—H10A | 119.6 | C27Bi—C21B—H21B | 118.4 |
C11—C10—H10A | 119.6 | C21B—C22B—C23B | 121.7 (11) |
C10—C11—C6 | 118.8 (2) | C21B—C22B—H22B | 119.1 |
C10—C11—C12 | 123.8 (2) | C23B—C22B—H22B | 119.1 |
C6—C11—C12 | 117.3 (2) | C24B—C23B—C22B | 120.7 (9) |
C18—C12—C11 | 123.0 (2) | C24B—C23B—H23B | 119.6 |
C18—C12—C13 | 121.9 (2) | C22B—C23B—H23B | 119.6 |
C11—C12—C13 | 114.9 (2) | C23B—C24B—C25B | 119.5 (10) |
C14—C13—C4 | 120.1 (2) | C23B—C24B—H24B | 120.2 |
C14—C13—C12 | 122.3 (2) | C25B—C24B—H24B | 120.2 |
C4—C13—C12 | 117.6 (2) | C26B—C25B—C24B | 123.4 (12) |
C1—C14—C13 | 119.6 (2) | C26B—C25B—C27Bi | 116.7 (17) |
C1—C14—H14A | 120.2 | C24B—C25B—C27Bi | 119.9 (16) |
C13—C14—H14A | 120.2 | C25B—C26B—C27B | 122.0 (13) |
C5—C15—C17 | 123.4 (3) | C25B—C26B—H26B | 119.0 |
C5—C15—C16 | 123.3 (2) | C27B—C26B—H26B | 119.0 |
C17—C15—C16 | 113.1 (2) | C26B—C27B—C21Bi | 124 (2) |
N1—C16—C15 | 178.0 (3) | C26B—C27B—C25Bi | 121 (2) |
N2—C17—C15 | 175.1 (3) | C21Bi—C27B—C25Bi | 114.7 (19) |
| | | |
C14—C1—C2—C3 | −1.7 (4) | C18—C12—C13—C14 | 41.2 (4) |
I1—C1—C2—C3 | 177.5 (2) | C11—C12—C13—C14 | −142.8 (2) |
C1—C2—C3—C4 | 0.4 (4) | C18—C12—C13—C4 | −140.0 (3) |
C2—C3—C4—C13 | 1.1 (4) | C11—C12—C13—C4 | 36.0 (3) |
C2—C3—C4—C5 | −177.5 (2) | C2—C1—C14—C13 | 1.4 (4) |
C3—C4—C5—C15 | −38.6 (4) | I1—C1—C14—C13 | −177.79 (19) |
C13—C4—C5—C15 | 142.9 (2) | C4—C13—C14—C1 | 0.2 (4) |
C3—C4—C5—C6 | 144.8 (2) | C12—C13—C14—C1 | 179.0 (2) |
C13—C4—C5—C6 | −33.8 (3) | C4—C5—C15—C17 | −168.8 (2) |
C15—C5—C6—C7 | 42.4 (4) | C6—C5—C15—C17 | 7.7 (4) |
C4—C5—C6—C7 | −140.9 (2) | C4—C5—C15—C16 | 4.9 (4) |
C15—C5—C6—C11 | −141.1 (2) | C6—C5—C15—C16 | −178.7 (2) |
C4—C5—C6—C11 | 35.6 (3) | C11—C12—C18—C19 | −171.6 (2) |
C11—C6—C7—C8 | 0.7 (4) | C13—C12—C18—C19 | 4.1 (4) |
C5—C6—C7—C8 | 177.1 (2) | C11—C12—C18—C20 | −1.5 (4) |
C6—C7—C8—C9 | 1.3 (4) | C13—C12—C18—C20 | 174.2 (2) |
C6—C7—C8—I2 | −176.85 (19) | C27i—C21—C22—C23 | 1 (2) |
C7—C8—C9—C10 | −1.3 (4) | C21—C22—C23—C24 | 1.2 (14) |
I2—C8—C9—C10 | 176.8 (2) | C22—C23—C24—C25 | 0.0 (18) |
C8—C9—C10—C11 | −0.7 (4) | C23—C24—C25—C26 | 177.2 (19) |
C9—C10—C11—C6 | 2.6 (4) | C23—C24—C25—C27i | −3 (3) |
C9—C10—C11—C12 | −174.9 (2) | C27i—C25—C26—C27 | −1 (4) |
C7—C6—C11—C10 | −2.6 (4) | C24—C25—C26—C27 | 178.8 (18) |
C5—C6—C11—C10 | −179.2 (2) | C25—C26—C27—C25i | 1 (4) |
C7—C6—C11—C12 | 175.1 (2) | C25—C26—C27—C21i | −175 (2) |
C5—C6—C11—C12 | −1.5 (3) | C27Bi—C21B—C22B—C23B | −4 (4) |
C10—C11—C12—C18 | −40.7 (4) | C21B—C22B—C23B—C24B | 1 (3) |
C6—C11—C12—C18 | 141.7 (3) | C22B—C23B—C24B—C25B | −1 (3) |
C10—C11—C12—C13 | 143.3 (2) | C23B—C24B—C25B—C26B | −177 (4) |
C6—C11—C12—C13 | −34.2 (3) | C23B—C24B—C25B—C27Bi | 4 (6) |
C3—C4—C13—C14 | −1.4 (4) | C24B—C25B—C26B—C27B | −177 (3) |
C5—C4—C13—C14 | 177.2 (2) | C27Bi—C25B—C26B—C27B | 2 (7) |
C3—C4—C13—C12 | 179.7 (2) | C25B—C26B—C27B—C21Bi | 174 (4) |
C5—C4—C13—C12 | −1.6 (3) | C25B—C26B—C27B—C25Bi | −2 (7) |
Symmetry code: (i) −x, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···N3ii | 0.93 | 2.63 | 3.296 (4) | 129 |
C9—H9···N2iii | 0.93 | 2.59 | 3.432 (4) | 151 |
Symmetry codes: (ii) x, y−1, 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
C20H6I2N4·0.5C16H10 | Z = 2 |
Mr = 657.21 | F(000) = 626 |
Triclinic, P1 | Dx = 1.789 Mg m−3 |
a = 8.7758 (13) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.0214 (17) Å | Cell parameters from 9953 reflections |
c = 13.3155 (19) Å | θ = 2.5–24.9° |
α = 66.461 (7)° | µ = 2.60 mm−1 |
β = 74.489 (7)° | T = 273 K |
γ = 74.462 (7)° | Prism, red |
V = 1220.2 (3) Å3 | 0.16 × 0.10 × 0.10 mm |
Data collection top
Bruker Kappa APEXII CCD diffractometer | 4480 independent reflections |
Radiation source: fine-focus sealed tube | 3844 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
profile data from φ and ω scans | θmax = 25.4°, θmin = 2.6° |
Absorption correction: integration (SADABS; Bruker, 2014) | h = −10→10 |
Tmin = 0.734, Tmax = 0.845 | k = −14→14 |
30806 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | 500 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-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 reflections | Δρmax = 0.97 e Å−3 |
426 parameters | Δρmin = −1.26 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
I1 | 0.74790 (3) | 0.05020 (3) | −0.02608 (3) | 0.05572 (11) | |
I2 | 0.25760 (5) | 0.70674 (4) | 0.39302 (3) | 0.08814 (16) | |
N3 | 1.0893 (4) | 0.0496 (4) | 0.2266 (4) | 0.0612 (10) | |
N4 | 1.0585 (4) | 0.3343 (4) | 0.3431 (3) | 0.0604 (10) | |
C1 | 0.6463 (4) | 0.1005 (3) | 0.1143 (3) | 0.0403 (8) | |
C2 | 0.4964 (5) | 0.0764 (4) | 0.1738 (3) | 0.0455 (9) | |
H2A | 0.4430 | 0.0325 | 0.1547 | 0.055* | |
C3 | 0.4261 (4) | 0.1174 (4) | 0.2614 (3) | 0.0427 (9) | |
H3A | 0.3243 | 0.1022 | 0.3002 | 0.051* | |
C4 | 0.5047 (4) | 0.1814 (3) | 0.2930 (3) | 0.0348 (7) | |
C5 | 0.4328 (4) | 0.2329 (4) | 0.3821 (3) | 0.0376 (8) | |
C6 | 0.4791 (4) | 0.3502 (4) | 0.3616 (3) | 0.0386 (8) | |
C7 | 0.3711 (5) | 0.4462 (4) | 0.3893 (3) | 0.0490 (10) | |
H7A | 0.2665 | 0.4365 | 0.4256 | 0.059* | |
C8 | 0.4206 (5) | 0.5564 (4) | 0.3626 (4) | 0.0536 (11) | |
C9 | 0.5766 (6) | 0.5720 (4) | 0.3116 (4) | 0.0543 (10) | |
H9A | 0.6088 | 0.6457 | 0.2963 | 0.065* | |
C10 | 0.6838 (5) | 0.4775 (4) | 0.2839 (3) | 0.0445 (9) | |
H10A | 0.7889 | 0.4877 | 0.2496 | 0.053* | |
C11 | 0.6374 (4) | 0.3668 (3) | 0.3062 (3) | 0.0354 (8) | |
C12 | 0.7432 (4) | 0.2682 (3) | 0.2693 (3) | 0.0331 (7) | |
C13 | 0.6602 (4) | 0.2015 (3) | 0.2344 (3) | 0.0333 (7) | |
C14 | 0.7291 (4) | 0.1620 (3) | 0.1449 (3) | 0.0368 (8) | |
H14A | 0.8309 | 0.1767 | 0.1053 | 0.044* | |
N1 | 0.261 (2) | −0.0356 (14) | 0.5130 (14) | 0.055 (3) | 0.61 (4) |
N2 | 0.243 (2) | 0.2268 (19) | 0.6549 (11) | 0.070 (3) | 0.61 (4) |
C15 | 0.339 (4) | 0.171 (2) | 0.4769 (15) | 0.043 (3) | 0.61 (4) |
C16 | 0.296 (2) | 0.0552 (17) | 0.4970 (16) | 0.045 (3) | 0.61 (4) |
C17 | 0.288 (2) | 0.2053 (16) | 0.5739 (10) | 0.049 (3) | 0.61 (4) |
N1B | 0.215 (3) | −0.010 (2) | 0.524 (2) | 0.060 (5) | 0.39 (4) |
N2B | 0.204 (3) | 0.273 (3) | 0.6355 (19) | 0.067 (4) | 0.39 (4) |
C15B | 0.329 (6) | 0.185 (4) | 0.477 (2) | 0.044 (3) | 0.39 (4) |
C16B | 0.271 (4) | 0.074 (3) | 0.501 (3) | 0.049 (4) | 0.39 (4) |
C17B | 0.258 (3) | 0.238 (3) | 0.5619 (17) | 0.049 (3) | 0.39 (4) |
C18 | 0.9032 (4) | 0.2366 (3) | 0.2703 (3) | 0.0355 (8) | |
C19 | 1.0039 (4) | 0.1322 (4) | 0.2438 (3) | 0.0428 (9) | |
C20 | 0.9868 (4) | 0.2937 (4) | 0.3109 (3) | 0.0423 (9) | |
C21 | 0.791 (3) | 0.682 (3) | 1.026 (3) | 0.077 (3) | 0.640 (6) |
H21 | 0.7001 | 0.7423 | 1.0279 | 0.093* | 0.640 (6) |
C22 | 0.7924 (10) | 0.5881 (8) | 0.9795 (7) | 0.065 (2) | 0.640 (6) |
C23 | 0.6650 (11) | 0.5838 (9) | 0.9391 (7) | 0.080 (2) | 0.640 (6) |
H23 | 0.5705 | 0.6416 | 0.9405 | 0.096* | 0.640 (6) |
C24 | 0.6792 (11) | 0.4963 (9) | 0.8984 (8) | 0.075 (2) | 0.640 (6) |
H24 | 0.5905 | 0.4947 | 0.8737 | 0.090* | 0.640 (6) |
C25 | 0.8082 (12) | 0.4116 (9) | 0.8901 (8) | 0.072 (2) | 0.640 (6) |
H25 | 0.8113 | 0.3564 | 0.8564 | 0.087* | 0.640 (6) |
C26 | 0.9347 (10) | 0.4972 (9) | 0.9790 (10) | 0.0555 (19) | 0.640 (6) |
C27 | 0.9463 (11) | 0.4059 (7) | 0.9347 (6) | 0.0643 (16) | 0.640 (6) |
C28 | 1.0891 (13) | 0.3172 (8) | 0.9353 (8) | 0.074 (2) | 0.640 (6) |
H28 | 1.0973 | 0.2560 | 0.9071 | 0.089* | 0.640 (6) |
C21B | 0.725 (2) | 0.6277 (15) | 0.9780 (15) | 0.076 (3) | 0.360 (6) |
H21B | 0.6208 | 0.6597 | 0.9649 | 0.092* | 0.360 (6) |
C22B | 0.8136 (15) | 0.5211 (12) | 0.9446 (11) | 0.066 (2) | 0.360 (6) |
C23B | 0.760 (2) | 0.4655 (16) | 0.8895 (16) | 0.075 (3) | 0.360 (6) |
H23B | 0.6586 | 0.4941 | 0.8707 | 0.091* | 0.360 (6) |
C24B | 0.8581 (19) | 0.3703 (13) | 0.8642 (13) | 0.074 (3) | 0.360 (6) |
H24B | 0.8203 | 0.3371 | 0.8253 | 0.089* | 0.360 (6) |
C25B | 0.9996 (18) | 0.3197 (13) | 0.8881 (12) | 0.076 (3) | 0.360 (6) |
H25B | 1.0584 | 0.2525 | 0.8681 | 0.091* | 0.360 (6) |
C26B | 0.9703 (18) | 0.4736 (15) | 0.9718 (19) | 0.057 (3) | 0.360 (6) |
C27B | 1.0654 (18) | 0.3699 (12) | 0.9470 (12) | 0.065 (3) | 0.360 (6) |
C28B | 1.219 (4) | 0.323 (5) | 0.978 (6) | 0.073 (5) | 0.360 (6) |
H28B | 1.2801 | 0.2521 | 0.9650 | 0.088* | 0.360 (6) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.05144 (17) | 0.0706 (2) | 0.0640 (2) | −0.01313 (14) | −0.00780 (13) | −0.04343 (16) |
I2 | 0.0970 (3) | 0.0790 (3) | 0.0804 (3) | 0.0256 (2) | −0.0165 (2) | −0.0463 (2) |
N3 | 0.040 (2) | 0.075 (3) | 0.078 (3) | −0.0009 (19) | −0.0118 (18) | −0.043 (2) |
N4 | 0.045 (2) | 0.074 (3) | 0.079 (3) | −0.0132 (18) | −0.0216 (19) | −0.036 (2) |
C1 | 0.040 (2) | 0.043 (2) | 0.043 (2) | −0.0046 (16) | −0.0134 (16) | −0.0184 (17) |
C2 | 0.043 (2) | 0.049 (2) | 0.053 (2) | −0.0155 (18) | −0.0151 (18) | −0.0185 (19) |
C3 | 0.0317 (19) | 0.053 (2) | 0.045 (2) | −0.0156 (17) | −0.0081 (16) | −0.0122 (18) |
C4 | 0.0292 (17) | 0.0400 (19) | 0.0331 (18) | −0.0068 (14) | −0.0108 (14) | −0.0073 (15) |
C5 | 0.0251 (17) | 0.052 (2) | 0.0333 (18) | −0.0049 (15) | −0.0088 (14) | −0.0117 (16) |
C6 | 0.0350 (19) | 0.051 (2) | 0.0308 (18) | −0.0052 (16) | −0.0088 (15) | −0.0153 (16) |
C7 | 0.041 (2) | 0.066 (3) | 0.040 (2) | −0.0015 (19) | −0.0080 (17) | −0.024 (2) |
C8 | 0.062 (3) | 0.054 (3) | 0.047 (2) | 0.012 (2) | −0.019 (2) | −0.028 (2) |
C9 | 0.068 (3) | 0.046 (2) | 0.053 (2) | −0.009 (2) | −0.017 (2) | −0.019 (2) |
C10 | 0.046 (2) | 0.047 (2) | 0.043 (2) | −0.0114 (18) | −0.0094 (17) | −0.0162 (18) |
C11 | 0.0360 (18) | 0.0412 (19) | 0.0299 (17) | −0.0060 (15) | −0.0112 (14) | −0.0108 (15) |
C12 | 0.0319 (17) | 0.0392 (19) | 0.0271 (17) | −0.0126 (15) | −0.0039 (13) | −0.0076 (14) |
C13 | 0.0298 (17) | 0.0363 (18) | 0.0327 (18) | −0.0080 (14) | −0.0097 (14) | −0.0073 (15) |
C14 | 0.0321 (18) | 0.044 (2) | 0.0352 (19) | −0.0114 (15) | −0.0057 (14) | −0.0121 (16) |
N1 | 0.046 (7) | 0.051 (6) | 0.050 (5) | −0.006 (5) | 0.006 (5) | −0.011 (4) |
N2 | 0.077 (7) | 0.077 (8) | 0.049 (5) | −0.008 (6) | −0.002 (4) | −0.023 (5) |
C15 | 0.029 (4) | 0.058 (5) | 0.038 (3) | −0.007 (5) | −0.007 (3) | −0.015 (3) |
C16 | 0.031 (5) | 0.057 (6) | 0.037 (3) | −0.006 (5) | −0.001 (3) | −0.010 (3) |
C17 | 0.038 (5) | 0.058 (6) | 0.043 (4) | −0.006 (4) | −0.004 (3) | −0.015 (4) |
N1B | 0.040 (8) | 0.056 (9) | 0.057 (7) | −0.005 (7) | 0.014 (7) | −0.010 (6) |
N2B | 0.062 (9) | 0.074 (10) | 0.056 (7) | −0.010 (7) | −0.003 (6) | −0.021 (7) |
C15B | 0.029 (5) | 0.059 (6) | 0.039 (4) | −0.010 (6) | −0.006 (4) | −0.012 (4) |
C16B | 0.031 (6) | 0.059 (6) | 0.040 (5) | −0.003 (6) | 0.000 (4) | −0.007 (5) |
C17B | 0.035 (6) | 0.064 (7) | 0.041 (5) | −0.008 (6) | −0.007 (4) | −0.012 (5) |
C18 | 0.0311 (18) | 0.043 (2) | 0.0333 (18) | −0.0131 (15) | −0.0035 (14) | −0.0123 (15) |
C19 | 0.0318 (19) | 0.057 (2) | 0.046 (2) | −0.0125 (18) | −0.0076 (16) | −0.0209 (19) |
C20 | 0.0316 (19) | 0.054 (2) | 0.044 (2) | −0.0098 (17) | −0.0068 (16) | −0.0184 (18) |
C21 | 0.078 (5) | 0.052 (5) | 0.066 (5) | −0.005 (4) | 0.002 (4) | 0.001 (4) |
C22 | 0.061 (3) | 0.058 (4) | 0.051 (3) | −0.012 (3) | −0.007 (3) | 0.005 (3) |
C23 | 0.073 (4) | 0.075 (4) | 0.063 (3) | −0.012 (3) | −0.014 (3) | 0.005 (3) |
C24 | 0.077 (4) | 0.074 (4) | 0.063 (3) | −0.022 (3) | −0.019 (3) | −0.002 (3) |
C25 | 0.087 (4) | 0.062 (4) | 0.062 (3) | −0.021 (3) | −0.009 (3) | −0.014 (3) |
C26 | 0.065 (4) | 0.048 (3) | 0.040 (3) | −0.020 (3) | −0.005 (3) | 0.002 (3) |
C27 | 0.079 (3) | 0.056 (3) | 0.049 (3) | −0.023 (3) | −0.009 (3) | −0.004 (2) |
C28 | 0.093 (4) | 0.054 (4) | 0.059 (4) | −0.017 (4) | −0.005 (3) | −0.008 (3) |
C21B | 0.072 (5) | 0.065 (5) | 0.065 (4) | −0.012 (4) | −0.007 (4) | 0.001 (4) |
C22B | 0.073 (3) | 0.060 (3) | 0.053 (3) | −0.021 (3) | −0.011 (3) | −0.003 (3) |
C23B | 0.079 (4) | 0.070 (4) | 0.062 (4) | −0.018 (4) | −0.012 (4) | −0.006 (4) |
C24B | 0.087 (5) | 0.066 (4) | 0.061 (4) | −0.022 (4) | −0.008 (4) | −0.012 (4) |
C25B | 0.092 (4) | 0.060 (4) | 0.061 (4) | −0.020 (4) | 0.000 (4) | −0.011 (4) |
C26B | 0.067 (4) | 0.051 (4) | 0.041 (4) | −0.018 (4) | −0.007 (4) | −0.002 (4) |
C27B | 0.081 (4) | 0.053 (4) | 0.048 (4) | −0.017 (4) | −0.001 (4) | −0.010 (4) |
C28B | 0.086 (6) | 0.054 (6) | 0.058 (6) | −0.008 (6) | −0.002 (6) | −0.008 (5) |
Geometric parameters (Å, º) top
I1—C1 | 2.093 (4) | C15B—C16B | 1.439 (9) |
I2—C8 | 2.089 (4) | C18—C19 | 1.440 (6) |
N3—C19 | 1.138 (5) | C18—C20 | 1.442 (5) |
N4—C20 | 1.137 (5) | C21—C28i | 1.290 (18) |
C1—C2 | 1.380 (5) | C21—C22 | 1.48 (2) |
C1—C14 | 1.387 (5) | C21—H21 | 0.9300 |
C2—C3 | 1.377 (6) | C22—C23 | 1.384 (13) |
C2—H2A | 0.9300 | C22—C26 | 1.423 (11) |
C3—C4 | 1.393 (5) | C23—C24 | 1.329 (14) |
C3—H3A | 0.9300 | C23—H23 | 0.9300 |
C4—C13 | 1.409 (5) | C24—C25 | 1.317 (13) |
C4—C5 | 1.472 (5) | C24—H24 | 0.9300 |
C5—C15B | 1.362 (8) | C25—C27 | 1.461 (12) |
C5—C15 | 1.362 (7) | C25—H25 | 0.9300 |
C5—C6 | 1.472 (5) | C26—C27 | 1.409 (10) |
C6—C7 | 1.391 (5) | C26—C26i | 1.431 (15) |
C6—C11 | 1.413 (5) | C27—C28 | 1.411 (14) |
C7—C8 | 1.386 (6) | C28—C21i | 1.290 (18) |
C7—H7A | 0.9300 | C28—H28 | 0.9300 |
C8—C9 | 1.382 (6) | C21B—C28Bi | 1.23 (4) |
C9—C10 | 1.374 (6) | C21B—C22B | 1.48 (2) |
C9—H9A | 0.9300 | C21B—H21B | 0.9300 |
C10—C11 | 1.390 (5) | C22B—C23B | 1.395 (15) |
C10—H10A | 0.9300 | C22B—C26B | 1.425 (12) |
C11—C12 | 1.464 (5) | C23B—C24B | 1.336 (15) |
C12—C18 | 1.355 (5) | C23B—H23B | 0.9300 |
C12—C13 | 1.477 (5) | C24B—C25B | 1.290 (14) |
C13—C14 | 1.387 (5) | C24B—H24B | 0.9300 |
C14—H14A | 0.9300 | C25B—C27B | 1.456 (14) |
N1—C16 | 1.135 (8) | C25B—H25B | 0.9300 |
N2—C17 | 1.151 (8) | C26B—C27B | 1.408 (12) |
C15—C17 | 1.437 (9) | C26B—C26Bi | 1.42 (2) |
C15—C16 | 1.439 (8) | C27B—C28B | 1.420 (16) |
N1B—C16B | 1.137 (9) | C28B—C21Bi | 1.23 (4) |
N2B—C17B | 1.151 (9) | C28B—H28B | 0.9300 |
C15B—C17B | 1.436 (10) | | |
| | | |
C2—C1—C14 | 120.4 (3) | C12—C18—C19 | 123.2 (3) |
C2—C1—I1 | 120.4 (3) | C12—C18—C20 | 123.9 (3) |
C14—C1—I1 | 119.2 (3) | C19—C18—C20 | 112.5 (3) |
C3—C2—C1 | 119.8 (3) | N3—C19—C18 | 176.0 (4) |
C3—C2—H2A | 120.1 | N4—C20—C18 | 176.8 (4) |
C1—C2—H2A | 120.1 | C28i—C21—C22 | 123.2 (12) |
C2—C3—C4 | 121.3 (3) | C28i—C21—H21 | 118.4 |
C2—C3—H3A | 119.4 | C22—C21—H21 | 118.4 |
C4—C3—H3A | 119.4 | C23—C22—C26 | 119.4 (10) |
C3—C4—C13 | 118.4 (3) | C23—C22—C21 | 124.3 (9) |
C3—C4—C5 | 123.8 (3) | C26—C22—C21 | 116.2 (8) |
C13—C4—C5 | 117.7 (3) | C24—C23—C22 | 119.4 (9) |
C15B—C5—C6 | 118.7 (11) | C24—C23—H23 | 120.3 |
C15—C5—C6 | 124.7 (7) | C22—C23—H23 | 120.3 |
C15B—C5—C4 | 126.8 (11) | C25—C24—C23 | 125.5 (9) |
C15—C5—C4 | 120.8 (7) | C25—C24—H24 | 117.2 |
C6—C5—C4 | 114.5 (3) | C23—C24—H24 | 117.2 |
C7—C6—C11 | 119.5 (4) | C24—C25—C27 | 118.9 (9) |
C7—C6—C5 | 122.5 (3) | C24—C25—H25 | 120.5 |
C11—C6—C5 | 118.0 (3) | C27—C25—H25 | 120.5 |
C8—C7—C6 | 119.5 (4) | C27—C26—C22 | 119.8 (7) |
C8—C7—H7A | 120.3 | C27—C26—C26i | 121.4 (9) |
C6—C7—H7A | 120.3 | C22—C26—C26i | 118.8 (10) |
C9—C8—C7 | 121.4 (4) | C26—C27—C28 | 118.4 (8) |
C9—C8—I2 | 118.0 (3) | C26—C27—C25 | 116.8 (8) |
C7—C8—I2 | 120.6 (3) | C28—C27—C25 | 124.8 (7) |
C10—C9—C8 | 119.4 (4) | C21i—C28—C27 | 122.0 (12) |
C10—C9—H9A | 120.3 | C21i—C28—H28 | 119.0 |
C8—C9—H9A | 120.3 | C27—C28—H28 | 119.0 |
C9—C10—C11 | 121.0 (4) | C28Bi—C21B—C22B | 124.6 (18) |
C9—C10—H10A | 119.5 | C28Bi—C21B—H21B | 117.7 |
C11—C10—H10A | 119.5 | C22B—C21B—H21B | 117.7 |
C10—C11—C6 | 119.3 (3) | C23B—C22B—C26B | 118.4 (12) |
C10—C11—C12 | 122.7 (3) | C23B—C22B—C21B | 127.1 (11) |
C6—C11—C12 | 117.9 (3) | C26B—C22B—C21B | 114.5 (12) |
C18—C12—C11 | 123.4 (3) | C24B—C23B—C22B | 118.9 (12) |
C18—C12—C13 | 122.2 (3) | C24B—C23B—H23B | 120.5 |
C11—C12—C13 | 114.4 (3) | C22B—C23B—H23B | 120.5 |
C14—C13—C4 | 120.0 (3) | C25B—C24B—C23B | 126.7 (13) |
C14—C13—C12 | 121.9 (3) | C25B—C24B—H24B | 116.7 |
C4—C13—C12 | 118.0 (3) | C23B—C24B—H24B | 116.7 |
C1—C14—C13 | 120.0 (3) | C24B—C25B—C27B | 118.7 (11) |
C1—C14—H14A | 120.0 | C24B—C25B—H25B | 120.6 |
C13—C14—H14A | 120.0 | C27B—C25B—H25B | 120.6 |
C5—C15—C17 | 123.2 (10) | C27B—C26B—C26Bi | 119.2 (13) |
C5—C15—C16 | 124.4 (11) | C27B—C26B—C22B | 120.1 (10) |
C17—C15—C16 | 112.1 (7) | C26Bi—C26B—C22B | 120.6 (13) |
N1—C16—C15 | 179.6 (15) | C26B—C27B—C28B | 118.6 (13) |
N2—C17—C15 | 175.7 (12) | C26B—C27B—C25B | 117.1 (11) |
C5—C15B—C17B | 125.7 (16) | C28B—C27B—C25B | 124.3 (13) |
C5—C15B—C16B | 122.1 (17) | C21Bi—C28B—C27B | 122 (2) |
C17B—C15B—C16B | 112.1 (10) | C21Bi—C28B—H28B | 118.8 |
N1B—C16B—C15B | 175 (2) | C27B—C28B—H28B | 118.8 |
N2B—C17B—C15B | 175 (2) | | |
| | | |
C14—C1—C2—C3 | 2.4 (6) | C4—C5—C15—C17 | 169.1 (18) |
I1—C1—C2—C3 | −175.6 (3) | C6—C5—C15—C16 | −179.2 (15) |
C1—C2—C3—C4 | −1.2 (6) | C4—C5—C15—C16 | −3 (3) |
C2—C3—C4—C13 | −1.1 (5) | C6—C5—C15B—C17B | 0 (6) |
C2—C3—C4—C5 | 176.8 (4) | C4—C5—C15B—C17B | −179 (3) |
C3—C4—C5—C15B | 34 (3) | C6—C5—C15B—C16B | 177 (3) |
C13—C4—C5—C15B | −148 (3) | C4—C5—C15B—C16B | −2 (6) |
C3—C4—C5—C15 | 38 (2) | C11—C12—C18—C19 | 174.0 (3) |
C13—C4—C5—C15 | −144 (2) | C13—C12—C18—C19 | −3.6 (5) |
C3—C4—C5—C6 | −144.9 (3) | C11—C12—C18—C20 | 1.9 (6) |
C13—C4—C5—C6 | 33.1 (4) | C13—C12—C18—C20 | −175.6 (3) |
C15B—C5—C6—C7 | −38 (3) | C28i—C21—C22—C23 | 179 (2) |
C15—C5—C6—C7 | −43 (2) | C28i—C21—C22—C26 | 0 (4) |
C4—C5—C6—C7 | 140.8 (3) | C26—C22—C23—C24 | −1.4 (13) |
C15B—C5—C6—C11 | 145 (3) | C21—C22—C23—C24 | 180 (2) |
C15—C5—C6—C11 | 141 (2) | C22—C23—C24—C25 | −1.6 (14) |
C4—C5—C6—C11 | −35.7 (4) | C23—C24—C25—C27 | 4.0 (14) |
C11—C6—C7—C8 | −0.2 (5) | C23—C22—C26—C27 | 1.7 (15) |
C5—C6—C7—C8 | −176.7 (3) | C21—C22—C26—C27 | −179 (2) |
C6—C7—C8—C9 | −1.8 (6) | C23—C22—C26—C26i | −180.0 (12) |
C6—C7—C8—I2 | 175.8 (3) | C21—C22—C26—C26i | −1 (3) |
C7—C8—C9—C10 | 2.0 (6) | C22—C26—C27—C28 | 179.9 (9) |
I2—C8—C9—C10 | −175.7 (3) | C26i—C26—C27—C28 | 1.7 (19) |
C8—C9—C10—C11 | 0.0 (6) | C22—C26—C27—C25 | 0.6 (14) |
C9—C10—C11—C6 | −2.1 (5) | C26i—C26—C27—C25 | −177.7 (13) |
C9—C10—C11—C12 | 174.4 (4) | C24—C25—C27—C26 | −3.3 (13) |
C7—C6—C11—C10 | 2.2 (5) | C24—C25—C27—C28 | 177.4 (8) |
C5—C6—C11—C10 | 178.8 (3) | C26—C27—C28—C21i | −1 (3) |
C7—C6—C11—C12 | −174.5 (3) | C25—C27—C28—C21i | 178 (2) |
C5—C6—C11—C12 | 2.2 (5) | C28Bi—C21B—C22B—C23B | −176 (5) |
C10—C11—C12—C18 | 39.3 (5) | C28Bi—C21B—C22B—C26B | 3 (5) |
C6—C11—C12—C18 | −144.2 (3) | C26B—C22B—C23B—C24B | 0 (3) |
C10—C11—C12—C13 | −143.1 (3) | C21B—C22B—C23B—C24B | 178.9 (15) |
C6—C11—C12—C13 | 33.5 (4) | C22B—C23B—C24B—C25B | 2 (3) |
C3—C4—C13—C14 | 2.4 (5) | C23B—C24B—C25B—C27B | −1 (3) |
C5—C4—C13—C14 | −175.7 (3) | C23B—C22B—C26B—C27B | −2 (3) |
C3—C4—C13—C12 | −179.4 (3) | C21B—C22B—C26B—C27B | 178.4 (18) |
C5—C4—C13—C12 | 2.6 (5) | C23B—C22B—C26B—C26Bi | −180 (3) |
C18—C12—C13—C14 | −40.1 (5) | C21B—C22B—C26B—C26Bi | 1 (3) |
C11—C12—C13—C14 | 142.2 (3) | C26Bi—C26B—C27B—C28B | −1 (5) |
C18—C12—C13—C4 | 141.7 (3) | C22B—C26B—C27B—C28B | −178 (4) |
C11—C12—C13—C4 | −36.1 (4) | C26Bi—C26B—C27B—C25B | −179 (2) |
C2—C1—C14—C13 | −1.1 (6) | C22B—C26B—C27B—C25B | 3 (3) |
I1—C1—C14—C13 | 176.8 (3) | C24B—C25B—C27B—C26B | −2 (2) |
C4—C13—C14—C1 | −1.2 (5) | C24B—C25B—C27B—C28B | 180 (4) |
C12—C13—C14—C1 | −179.5 (3) | C26B—C27B—C28B—C21Bi | −3 (9) |
C6—C5—C15—C17 | −7 (4) | C25B—C27B—C28B—C21Bi | 176 (5) |
Symmetry code: (i) −x+2, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···I1ii | 0.93 | 3.24 | 4.144 (4) | 164 |
C9—H9···N2iii | 0.93 | 2.60 | 3.443 (17) | 150 |
C9—H9···N2Biii | 0.93 | 2.62 | 3.38 (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
C20H6I2N4·0.5C6H4S4 | Z = 2 |
Mr = 658.25 | F(000) = 624 |
Triclinic, P1 | Dx = 1.936 Mg m−3 |
a = 8.615 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.631 (3) Å | Cell parameters from 9509 reflections |
c = 12.450 (3) Å | θ = 2.6–27.2° |
α = 80.247 (9)° | µ = 2.99 mm−1 |
β = 74.695 (9)° | T = 273 K |
γ = 70.392 (8)° | Prism, black |
V = 1129.0 (5) Å3 | 0.46 × 0.27 × 0.12 mm |
Data collection top
Bruker D8 Venture/Photon 100 diffractometer | 4993 independent reflections |
Radiation source: microfocus sealed tube | 4572 reflections with I > 2σ(I) |
Multilayer mirrors monochromator | Rint = 0.027 |
profile data from φ and ω scans | θmax = 27.2°, θmin = 2.4° |
Absorption correction: integration (SADABS; Bruker, 2014) | h = −11→11 |
Tmin = 0.926, Tmax = 0.978 | k = −14→14 |
29346 measured reflections | l = −15→15 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-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 = 1.04 | Δρmax = 1.71 e Å−3 |
4993 reflections | Δρmin = −1.20 e Å−3 |
281 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction 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 | x | y | z | Uiso*/Ueq | |
I1 | 0.79542 (4) | 1.18759 (3) | 0.96735 (3) | 0.05333 (13) | |
I2 | 1.25872 (5) | 0.29582 (3) | 0.57238 (3) | 0.07177 (15) | |
N1 | 1.2833 (7) | 1.0080 (5) | 0.4452 (4) | 0.0795 (14) | |
N2 | 1.2746 (7) | 0.6866 (5) | 0.3438 (4) | 0.0766 (14) | |
N3 | 0.4216 (5) | 1.0444 (4) | 0.8397 (5) | 0.0657 (12) | |
N4 | 0.4563 (5) | 0.7109 (4) | 0.7340 (4) | 0.0601 (10) | |
C1 | 0.9011 (5) | 1.0500 (3) | 0.8589 (3) | 0.0388 (8) | |
C2 | 1.0566 (5) | 1.0435 (4) | 0.7869 (4) | 0.0421 (8) | |
H2 | 1.1132 | 1.0980 | 0.7900 | 0.051* | |
C3 | 1.1270 (5) | 0.9564 (4) | 0.7110 (3) | 0.0401 (8) | |
H3 | 1.2332 | 0.9505 | 0.6650 | 0.048* | |
C4 | 1.0414 (4) | 0.8766 (3) | 0.7020 (3) | 0.0350 (7) | |
C5 | 1.1037 (4) | 0.7892 (3) | 0.6161 (3) | 0.0360 (7) | |
C6 | 1.0562 (5) | 0.6759 (3) | 0.6477 (3) | 0.0370 (7) | |
C7 | 1.1595 (5) | 0.5644 (4) | 0.6067 (3) | 0.0437 (9) | |
H7 | 1.2625 | 0.5598 | 0.5568 | 0.052* | |
C8 | 1.1085 (6) | 0.4604 (4) | 0.6402 (4) | 0.0461 (9) | |
C9 | 0.9592 (6) | 0.4636 (4) | 0.7182 (4) | 0.0454 (9) | |
H9 | 0.9278 | 0.3927 | 0.7420 | 0.054* | |
C10 | 0.8578 (5) | 0.5732 (4) | 0.7600 (3) | 0.0400 (8) | |
H10 | 0.7579 | 0.5757 | 0.8128 | 0.048* | |
C11 | 0.9022 (4) | 0.6802 (3) | 0.7246 (3) | 0.0350 (7) | |
C12 | 0.7950 (4) | 0.7993 (3) | 0.7659 (3) | 0.0329 (7) | |
C13 | 0.8846 (4) | 0.8827 (3) | 0.7772 (3) | 0.0331 (7) | |
C14 | 0.8180 (5) | 0.9676 (3) | 0.8569 (3) | 0.0368 (7) | |
H14 | 0.7176 | 0.9689 | 0.9087 | 0.044* | |
C15 | 1.1941 (5) | 0.8135 (4) | 0.5111 (3) | 0.0423 (8) | |
C16 | 1.2413 (6) | 0.9236 (4) | 0.4769 (4) | 0.0516 (10) | |
C17 | 1.2375 (6) | 0.7395 (5) | 0.4204 (4) | 0.0549 (11) | |
C18 | 0.6243 (4) | 0.8335 (3) | 0.7830 (3) | 0.0362 (7) | |
C19 | 0.5145 (5) | 0.9524 (4) | 0.8147 (4) | 0.0447 (9) | |
C20 | 0.5350 (5) | 0.7613 (4) | 0.7567 (4) | 0.0432 (9) | |
S1 | 0.20489 (15) | 0.56951 (10) | 0.90038 (10) | 0.0505 (3) | |
S2 | 0.17172 (15) | 0.32114 (10) | 0.94620 (10) | 0.0509 (3) | |
C21 | 0.0782 (5) | 0.4771 (4) | 0.9691 (3) | 0.0416 (8) | |
C22 | 0.3719 (6) | 0.4506 (4) | 0.8411 (5) | 0.0583 (12) | |
H22 | 0.4695 | 0.4648 | 0.7957 | 0.070* | |
C23 | 0.3572 (5) | 0.3372 (4) | 0.8623 (4) | 0.0558 (11) | |
H23 | 0.4441 | 0.2701 | 0.8327 | 0.067* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0614 (2) | 0.04952 (18) | 0.05221 (19) | −0.01940 (14) | −0.00738 (13) | −0.01638 (13) |
I2 | 0.0840 (3) | 0.0458 (2) | 0.0699 (2) | −0.00116 (16) | −0.00381 (19) | −0.02337 (15) |
N1 | 0.101 (4) | 0.083 (3) | 0.053 (3) | −0.045 (3) | −0.006 (2) | 0.013 (2) |
N2 | 0.077 (3) | 0.104 (4) | 0.050 (2) | −0.039 (3) | 0.009 (2) | −0.025 (2) |
N3 | 0.0398 (19) | 0.049 (2) | 0.107 (4) | −0.0096 (17) | −0.007 (2) | −0.025 (2) |
N4 | 0.0417 (19) | 0.052 (2) | 0.091 (3) | −0.0185 (17) | −0.012 (2) | −0.016 (2) |
C1 | 0.0401 (19) | 0.0373 (18) | 0.0399 (19) | −0.0118 (15) | −0.0090 (15) | −0.0057 (15) |
C2 | 0.0399 (19) | 0.042 (2) | 0.049 (2) | −0.0189 (16) | −0.0117 (17) | −0.0022 (17) |
C3 | 0.0312 (17) | 0.046 (2) | 0.043 (2) | −0.0158 (15) | −0.0047 (15) | 0.0003 (16) |
C4 | 0.0299 (16) | 0.0368 (18) | 0.0361 (18) | −0.0099 (14) | −0.0064 (14) | 0.0008 (14) |
C5 | 0.0267 (16) | 0.0402 (18) | 0.0367 (18) | −0.0071 (14) | −0.0055 (13) | −0.0007 (14) |
C6 | 0.0333 (17) | 0.0413 (19) | 0.0341 (17) | −0.0093 (14) | −0.0052 (14) | −0.0054 (14) |
C7 | 0.040 (2) | 0.045 (2) | 0.039 (2) | −0.0038 (16) | −0.0035 (16) | −0.0100 (16) |
C8 | 0.054 (2) | 0.0353 (19) | 0.044 (2) | −0.0019 (17) | −0.0115 (18) | −0.0129 (16) |
C9 | 0.051 (2) | 0.0365 (19) | 0.049 (2) | −0.0120 (17) | −0.0135 (18) | −0.0050 (16) |
C10 | 0.0392 (19) | 0.0398 (19) | 0.0408 (19) | −0.0128 (15) | −0.0086 (16) | −0.0016 (15) |
C11 | 0.0321 (17) | 0.0356 (17) | 0.0352 (17) | −0.0078 (14) | −0.0072 (14) | −0.0035 (14) |
C12 | 0.0332 (17) | 0.0350 (17) | 0.0288 (16) | −0.0132 (14) | −0.0015 (13) | −0.0008 (13) |
C13 | 0.0304 (16) | 0.0334 (17) | 0.0345 (17) | −0.0103 (13) | −0.0054 (13) | −0.0019 (13) |
C14 | 0.0324 (17) | 0.0382 (18) | 0.0374 (18) | −0.0116 (14) | −0.0034 (14) | −0.0022 (14) |
C15 | 0.0329 (18) | 0.049 (2) | 0.0389 (19) | −0.0105 (16) | −0.0014 (15) | −0.0026 (16) |
C16 | 0.051 (2) | 0.057 (3) | 0.039 (2) | −0.017 (2) | −0.0002 (18) | 0.0036 (19) |
C17 | 0.046 (2) | 0.074 (3) | 0.041 (2) | −0.023 (2) | 0.0038 (18) | −0.007 (2) |
C18 | 0.0307 (17) | 0.0342 (17) | 0.0401 (19) | −0.0114 (14) | −0.0002 (14) | −0.0029 (14) |
C19 | 0.0301 (18) | 0.042 (2) | 0.060 (2) | −0.0124 (16) | −0.0030 (17) | −0.0078 (18) |
C20 | 0.0315 (18) | 0.040 (2) | 0.052 (2) | −0.0095 (15) | −0.0001 (16) | −0.0064 (17) |
S1 | 0.0518 (6) | 0.0407 (5) | 0.0554 (6) | −0.0149 (4) | 0.0014 (5) | −0.0143 (4) |
S2 | 0.0518 (6) | 0.0380 (5) | 0.0569 (6) | −0.0120 (4) | −0.0028 (5) | −0.0071 (4) |
C21 | 0.044 (2) | 0.0396 (19) | 0.0395 (19) | −0.0117 (16) | −0.0059 (16) | −0.0065 (15) |
C22 | 0.041 (2) | 0.052 (3) | 0.080 (3) | −0.0157 (19) | 0.000 (2) | −0.019 (2) |
C23 | 0.036 (2) | 0.051 (2) | 0.075 (3) | −0.0045 (18) | −0.003 (2) | −0.026 (2) |
Geometric parameters (Å, º) top
I1—C1 | 2.079 (4) | C9—C10 | 1.377 (6) |
I2—C8 | 2.088 (4) | C9—H9 | 0.9300 |
N1—C16 | 1.132 (7) | C10—C11 | 1.390 (5) |
N2—C17 | 1.139 (6) | C10—H10 | 0.9300 |
N3—C19 | 1.135 (6) | C11—C12 | 1.473 (5) |
N4—C20 | 1.143 (6) | C12—C18 | 1.355 (5) |
C1—C14 | 1.381 (5) | C12—C13 | 1.470 (5) |
C1—C2 | 1.387 (6) | C13—C14 | 1.393 (5) |
C2—C3 | 1.378 (6) | C14—H14 | 0.9300 |
C2—H2 | 0.9300 | C15—C17 | 1.430 (6) |
C3—C4 | 1.398 (5) | C15—C16 | 1.435 (6) |
C3—H3 | 0.9300 | C18—C20 | 1.437 (5) |
C4—C13 | 1.413 (5) | C18—C19 | 1.440 (5) |
C4—C5 | 1.471 (5) | S1—C22 | 1.725 (5) |
C5—C15 | 1.371 (5) | S1—C21 | 1.750 (4) |
C5—C6 | 1.470 (5) | S2—C23 | 1.712 (5) |
C6—C7 | 1.395 (5) | S2—C21 | 1.759 (4) |
C6—C11 | 1.408 (5) | C21—C21i | 1.342 (8) |
C7—C8 | 1.385 (6) | C22—C23 | 1.343 (7) |
C7—H7 | 0.9300 | C22—H22 | 0.9300 |
C8—C9 | 1.386 (6) | C23—H23 | 0.9300 |
| | | |
C14—C1—C2 | 120.5 (4) | C6—C11—C12 | 117.9 (3) |
C14—C1—I1 | 121.1 (3) | C18—C12—C13 | 122.2 (3) |
C2—C1—I1 | 118.5 (3) | C18—C12—C11 | 121.5 (3) |
C3—C2—C1 | 119.9 (4) | C13—C12—C11 | 116.0 (3) |
C3—C2—H2 | 120.1 | C14—C13—C4 | 120.0 (3) |
C1—C2—H2 | 120.1 | C14—C13—C12 | 122.2 (3) |
C2—C3—C4 | 121.1 (3) | C4—C13—C12 | 117.8 (3) |
C2—C3—H3 | 119.5 | C1—C14—C13 | 120.0 (3) |
C4—C3—H3 | 119.5 | C1—C14—H14 | 120.0 |
C3—C4—C13 | 118.4 (3) | C13—C14—H14 | 120.0 |
C3—C4—C5 | 123.3 (3) | C5—C15—C17 | 124.5 (4) |
C13—C4—C5 | 118.3 (3) | C5—C15—C16 | 123.2 (4) |
C15—C5—C6 | 121.6 (4) | C17—C15—C16 | 112.1 (4) |
C15—C5—C4 | 122.5 (4) | N1—C16—C15 | 176.7 (5) |
C6—C5—C4 | 115.8 (3) | N2—C17—C15 | 175.6 (6) |
C7—C6—C11 | 119.0 (4) | C12—C18—C20 | 123.4 (3) |
C7—C6—C5 | 122.6 (3) | C12—C18—C19 | 123.8 (3) |
C11—C6—C5 | 118.4 (3) | C20—C18—C19 | 112.3 (3) |
C8—C7—C6 | 120.0 (4) | N3—C19—C18 | 176.8 (4) |
C8—C7—H7 | 120.0 | N4—C20—C18 | 175.5 (4) |
C6—C7—H7 | 120.0 | C22—S1—C21 | 94.9 (2) |
C7—C8—C9 | 121.1 (4) | C23—S2—C21 | 95.6 (2) |
C7—C8—I2 | 119.6 (3) | C21i—C21—S1 | 122.4 (4) |
C9—C8—I2 | 119.3 (3) | C21i—C21—S2 | 123.5 (4) |
C10—C9—C8 | 119.1 (4) | S1—C21—S2 | 114.0 (2) |
C10—C9—H9 | 120.5 | C23—C22—S1 | 118.3 (4) |
C8—C9—H9 | 120.5 | C23—C22—H22 | 120.9 |
C9—C10—C11 | 121.2 (4) | S1—C22—H22 | 120.9 |
C9—C10—H10 | 119.4 | C22—C23—S2 | 117.2 (3) |
C11—C10—H10 | 119.4 | C22—C23—H23 | 121.4 |
C10—C11—C6 | 119.6 (3) | S2—C23—H23 | 121.4 |
C10—C11—C12 | 122.6 (3) | | |
| | | |
C14—C1—C2—C3 | 1.6 (6) | C6—C11—C12—C13 | −32.9 (5) |
I1—C1—C2—C3 | −177.5 (3) | C3—C4—C13—C14 | 0.8 (5) |
C1—C2—C3—C4 | 2.5 (6) | C5—C4—C13—C14 | −177.4 (3) |
C2—C3—C4—C13 | −3.6 (6) | C3—C4—C13—C12 | 179.3 (3) |
C2—C3—C4—C5 | 174.5 (4) | C5—C4—C13—C12 | 1.1 (5) |
C3—C4—C5—C15 | −32.7 (6) | C18—C12—C13—C14 | 35.1 (5) |
C13—C4—C5—C15 | 145.4 (4) | C11—C12—C13—C14 | −150.3 (3) |
C3—C4—C5—C6 | 150.1 (4) | C18—C12—C13—C4 | −143.3 (4) |
C13—C4—C5—C6 | −31.8 (5) | C11—C12—C13—C4 | 31.2 (5) |
C15—C5—C6—C7 | 34.5 (6) | C2—C1—C14—C13 | −4.4 (6) |
C4—C5—C6—C7 | −148.3 (4) | I1—C1—C14—C13 | 174.7 (3) |
C15—C5—C6—C11 | −147.0 (4) | C4—C13—C14—C1 | 3.2 (5) |
C4—C5—C6—C11 | 30.2 (5) | C12—C13—C14—C1 | −175.3 (3) |
C11—C6—C7—C8 | 1.1 (6) | C6—C5—C15—C17 | 5.9 (6) |
C5—C6—C7—C8 | 179.5 (4) | C4—C5—C15—C17 | −171.1 (4) |
C6—C7—C8—C9 | −2.9 (6) | C6—C5—C15—C16 | 179.4 (4) |
C6—C7—C8—I2 | 177.1 (3) | C4—C5—C15—C16 | 2.4 (6) |
C7—C8—C9—C10 | 2.1 (6) | C13—C12—C18—C20 | 170.4 (3) |
I2—C8—C9—C10 | −177.9 (3) | C11—C12—C18—C20 | −3.9 (6) |
C8—C9—C10—C11 | 0.5 (6) | C13—C12—C18—C19 | −0.6 (6) |
C9—C10—C11—C6 | −2.3 (6) | C11—C12—C18—C19 | −174.9 (4) |
C9—C10—C11—C12 | 178.7 (4) | C22—S1—C21—C21i | −178.8 (5) |
C7—C6—C11—C10 | 1.5 (5) | C22—S1—C21—S2 | −0.5 (3) |
C5—C6—C11—C10 | −177.0 (3) | C23—S2—C21—C21i | 179.0 (5) |
C7—C6—C11—C12 | −179.5 (3) | C23—S2—C21—S1 | 0.7 (3) |
C5—C6—C11—C12 | 2.0 (5) | C21—S1—C22—C23 | 0.0 (5) |
C10—C11—C12—C18 | −39.3 (5) | S1—C22—C23—S2 | 0.5 (6) |
C6—C11—C12—C18 | 141.7 (4) | C21—S2—C23—C22 | −0.7 (5) |
C10—C11—C12—C13 | 146.1 (4) | | |
Symmetry code: (i) −x, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···N3ii | 0.93 | 2.68 | 3.310 (6) | 126 |
Symmetry code: (ii) x, y−1, z. |
Selected dihedral angles (°) [Please provide s.u. values] topThe 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–C11 | C1–C4/C13/C14 |
DITCAQ | 21.001 | 19.546 |
(I) | 21.445 | 19.462 |
(II) | 21.820 | 19.750 |
(III) | 16.569 | 12.834 |