research communications
of tetramethylammonium 1,1,7,7-tetracyanohepta-2,4,6-trienide
aDepartment of Chemistry, New Mexico Highlands University, Las Vegas, New Mexico, 87701, USA, and bSchool of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, 30332, USA
*Correspondence e-mail: bogdgv@gmail.com
The title compound, C4H12N+·C11H5N4−, contains one tetramethylammonium cation and one 1,1,7,7-tetracyanohepta-2,4,6-trienide anion in the The anion is in an all-trans conjugated C=C bonds conformation. Two terminal C(CN)2 dinitrile moieties are slightly twisted from the polymethine main chain to which they are attached [C(CN)2/C5 dihedral angles = 6.1 (2) and 7.1 (1)°]. The C—C bond distances along the heptadienyl chain vary in the narrow range 1.382 (2)–1.394 (2) Å, thus indicating the significant degree of conjugation. In the crystal, the anions are linked into zigzag chains along the [10] direction by C—H⋯N(nitrile) short contacts. The antiparallel chains stack along the [110] direction with alternating separations between the neighboring anions in stacks of 3.291 and 3.504 Å. The C—H⋯N short contacts and stacking interactions combine to link the anions into layers parallel to the (01) plane and separated by columns of tetramethylammonium cations.
Keywords: crystal structure; polymethines; carbanion; hepta-2,4,6-triene-1,1,7,7-tetracarbonitrile; stacking; weak interactions.
CCDC reference: 1947007
1. Chemical context
Polymethines, being fully conjugated hydrocarbons, represent the simplest `molecular wires' with potential uses in organic electronic applications thanks to their easily tuned band gaps, and their wide range of absorption covering the visible spectrum (Etemad & Heeger, 1982; Meisner et al., 2012; Jayamurugan et al., 2014). Crystallographic data for polymethines are rather scare because of their instability and low solubility (Chetkina & Bel'skii, 2002; Meisner et al., 2012; Tsuji & Hoffmann, 2016). A successful strategy to increase the chemical stability with respect to oxidative decomposition has been reported (Meisner et al., 2012) that includes the decoration of polyenes with cyano groups and which resulted in the synthesis of a library of odd-numbered members from three to thirteen linear conjugated and the determination of their crystal structures.
2. Structural commentary
The title compound (Fig. 1) crystallizes with one cation and one anion per both entities residing in general positions. The trimethylammonium cation has a common tetrahedral geometry (2460 hits for this cation in CSD version 5.40, last update November 2018; Groom et al., 2016), with three of the four methyl groups being disordered (see Refinement). In the linear anion, the bond lengths vary in the narrow range 1.382 (2)–1.394 (2) Å, thus indicating a significant degree of conjugation along the hydrocarbon chain. Such a structural and in which the difference in bond lengths along the conjugated backbone approaches zero is known as a cyanine-like structure (Marder et al., 1994). The anion is slightly distorted from a planar arrangement as shown by the r.m.s. deviation of 0.098 Å for non-hydrogen atoms from the least-square plane calculated through the entire carbanion. The dihedral angles between the perfectly planar terminal dicyano-groups, C(CN)2 and the linear C4–C8 central fragment in the anion are 6.1 (2) and 7.1 (1)°. The bond lengths and angles and the overall conformation of the anion are close to those reported for the same anion in N-(7-(dimethylamino)hepta-2,4,6-trienylidene)-N,N-dimethylammonium 1,1,7,7-tetracyanohepta-2,4,6-trienide (NEQHOH; Reck & Dahne, 2006), and for its dicyano derivative, 1,1,2,6,7,7-hexacyanoheptatrienide in the ammonium salt (Edmonds et al., 1970).
3. Supramolecular features
In the crystal, anions related by the twofold screw axis are linked by C4—H4⋯N3i short contacts (Table 1), forming zigzag chains along the [10] direction in which adjacent molecules have a nearly orthogonal arrangement, as indicated by the dihedral angle between their skeletons of 87.62°. The antiparallel chains stack along the [110] direction with alternating separations between neighboring anions in the stacks of 3.291 and 3.504 Å. The C—H⋯N short contacts (Table 1) and stacking interactions of 3.291 and 3.504 Å combine to form layers of anions parallel to the (01) plane and separated by columns of tetramethylammonium cations (Fig. 2). A similar arrangement with separation of the anionic and cationic regions was noted in the of tetramethylammonium 1,1,2,4,5,5-hexacyanopentadienide (HXCPEN; Sass & Nichols, 1974).
4. Database survey
The Cambridge Structural Database (CSD version 5.40, last update November 18, Groom et al., 2016) provides very scare solid-state structural information on linear oligoenes, a search for linear tetracyanoheptatrienide analogues of the title compound yielding only two structures: ammonium 1,1,2,6,7,7-hexacyanoheptatrienide (AHCNPI; Edmonds et al., 1970) and N-(7-(dimethylamino)hepta-2,4,6-trienylidene)-N,N-dimethylammonium 1,1,7,7-tetracyanohepta-2,4,6-trienide (NEQHOH; Reck & Dahne, 2006). The reported room-temperature data revealed the similar values for the bond lengths along the heptatrienide backbone, which are in the range 1.378–1.390 Å in AHCNPI (Fig. 3) and 1.368 (5)–1.389 (5) Å in NEQHOH (Fig. 4). For the two nearest homologues of the title compound with six and eight carbon atoms in the main chains, seven hits (DBPHCN and PHXTCN; Noerenberg et al., 1977; QAGXUU, QAGYAB, QAGYEF, QAGYIJ and QAGYOP; Jayamurugan et al., 2014) and one (QAGXOO, Jayamurugan et al., 2014) hit were found in the CSD, all of which represent individual molecules decorated by either phenyl or nitrile substituents.
5. Synthesis and crystallization
The synthesis is shown in Fig. 5.
N-(2,4-dinitrophenyl)pyridinium chloride. Pyridine (4.00 mL, 49.4 mmol) was added to a solution of 2,4-dinitrochlorobenzene (10.00 g, 49.37 mmol) in dry acetone (4 mL). The resulting mixture was brought to reflux for 1 h before being cooled to room temperature. The crude product was collected by filtration and recrystallized from ethanol to give N-(2,4-dinitrophenyl)pyridinium chloride (11.26 g, 91%), m.p. 462–463 K. 1H NMR (500 MHz, CDCl3) δ 9.38 (d, J = 5.3 Hz, 2H), 9.12 (d, J = 2.3 Hz, 1H), 8.99 (dd, J = 8.2, 2.3 Hz, 1H), 8.95 (t, J = 8.0 Hz, 1H), 8.44 (m, 3H).
Tetramethylammonium (2E,4E)-1,1,7,7-tetracyanohepta-2,4,6-trien-1-ide. Malononitrile (0.42 g, 6.3 mmol) was added to a refluxing solution of fresh sodium ethoxide, prepared by adding sodium metal (0.20 g, 8.7 mmol) to absolute ethanol (5 mL). To this solution, was added a solution of N-(2,4-dinitrophenyl)pyridinium chloride (0.71 g, 2.5 mmol) in ethanol (2 mL), and the reaction mixture was stirred at reflux for 1 h before being cooled to room temperature and stirred for a further hour. A solution of tetramethylammonium bromide (0.39 g, 2.5 mmol) in water (10 mL) was added to the reaction. After about an hour, the deep-red mixture was extracted with dichloromethane (3 × 30 mL), dried over magnesium sulfate, and the solvent was removed in vacuo. The deep-violet residue was purified by (silica gel, 10% acetone in CHCl2). 1H NMR (500 MHz, CDCl3) δ 7.06 (d, J = 12.9 Hz, 2H), 6.95 (t, J = 12.9 Hz, 1H), 6.06 (t, J = 12.8 Hz, 2H), 3.68 (s, 12H).
Crystallization. Crystals of the title compound were grown over a period of 2–4 weeks by the vapour-diffusion method using dichloromethane as the solvent and hexane as the non-solvent.
6. Refinement
Crystal data, data collection and structure . C-bound H atoms were fixed geometrically (C—H = 0.95–0.98 Å) and refined using a riding model, with Uiso(H) set to 1.2Ueq(C) for aromatic and 1.5Ueq(C-methyl). To obtain an idealized geometry of the cation, 1,2 and 1,3 restraints for C—N mean bond distances and C—N—C bond angles were used. In the tetramethyl ammonium cation, three methyl groups are each disordered over two positions about the N5—C12 axis and were refined with partial occupancies of 0.66 (1) and 0.34 (1). The positions of all disordered atoms were refined in an isotropic approximation.
details are summarized in Table 2Supporting information
CCDC reference: 1947007
https://doi.org/10.1107/S2056989019011411/nr2075sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019011411/nr2075Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989019011411/nr2075Isup3.cml
Data collection: APEX3 (Bruker, 2018); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2017 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C4H12N+·C11H5N4− | F(000) = 568 |
Mr = 267.33 | Dx = 1.136 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.6043 (5) Å | Cell parameters from 6241 reflections |
b = 9.4168 (4) Å | θ = 2.6–25.6° |
c = 16.4423 (7) Å | µ = 0.07 mm−1 |
β = 107.8856 (17)° | T = 150 K |
V = 1562.55 (12) Å3 | Block, light blue |
Z = 4 | 0.35 × 0.21 × 0.15 mm |
Bruker APEXII CCD diffractometer | 3657 reflections with I > 2σ(I) |
Radiation source: sealed X-ray tube | Rint = 0.097 |
φ and ω scans | θmax = 35.2°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −17→17 |
Tmin = 0.654, Tmax = 0.747 | k = −15→15 |
64536 measured reflections | l = −26→26 |
6914 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.221 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0941P)2 + 0.374P] where P = (Fo2 + 2Fc2)/3 |
6914 reflections | (Δ/σ)max < 0.001 |
179 parameters | Δρmax = 0.50 e Å−3 |
51 restraints | Δρmin = −0.51 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.54341 (16) | 0.24960 (18) | 0.22446 (9) | 0.0608 (4) | |
N2 | 0.36705 (18) | 0.37537 (19) | −0.04834 (9) | 0.0631 (4) | |
N3 | −0.17214 (16) | 0.90748 (17) | −0.16118 (8) | 0.0548 (4) | |
N4 | −0.29656 (17) | 1.11815 (18) | 0.04221 (10) | 0.0617 (4) | |
C1 | 0.46618 (16) | 0.31235 (16) | 0.17174 (9) | 0.0439 (3) | |
C2 | 0.37143 (14) | 0.39111 (14) | 0.10849 (8) | 0.0375 (3) | |
C3 | 0.37173 (16) | 0.37974 (16) | 0.02231 (9) | 0.0433 (3) | |
C4 | 0.28203 (14) | 0.48084 (14) | 0.12984 (8) | 0.0360 (3) | |
H4 | 0.286927 | 0.486600 | 0.188411 | 0.043* | |
C5 | 0.18676 (15) | 0.56214 (15) | 0.07251 (8) | 0.0391 (3) | |
H5 | 0.178726 | 0.553107 | 0.013587 | 0.047* | |
C6 | 0.10204 (14) | 0.65596 (15) | 0.09478 (8) | 0.0374 (3) | |
H6 | 0.107502 | 0.663852 | 0.153364 | 0.045* | |
C7 | 0.00981 (15) | 0.73879 (15) | 0.03587 (8) | 0.0385 (3) | |
H7 | 0.001958 | 0.726481 | −0.022824 | 0.046* | |
C8 | −0.07162 (13) | 0.83809 (14) | 0.05642 (8) | 0.0356 (3) | |
H8 | −0.068286 | 0.846208 | 0.114637 | 0.043* | |
C9 | −0.15824 (14) | 0.92700 (15) | −0.00276 (8) | 0.0363 (3) | |
C10 | −0.16767 (14) | 0.91795 (16) | −0.09079 (9) | 0.0400 (3) | |
C11 | −0.23544 (16) | 1.03238 (17) | 0.02185 (9) | 0.0432 (3) | |
N5 | 0.93087 (11) | 0.33415 (12) | 0.26390 (7) | 0.0352 (2) | |
C12 | 0.90376 (19) | 0.17881 (17) | 0.25738 (11) | 0.0514 (4) | |
H12A | 0.924319 | 0.138185 | 0.314851 | 0.077* | |
H12B | 0.810076 | 0.162583 | 0.226183 | 0.077* | |
H12C | 0.959035 | 0.133384 | 0.226798 | 0.077* | |
C13 | 0.8536 (4) | 0.4046 (3) | 0.18099 (17) | 0.0490 (7)* | 0.663 (9) |
H13A | 0.871124 | 0.507013 | 0.184931 | 0.073* | 0.663 (9) |
H13B | 0.881000 | 0.364754 | 0.133987 | 0.073* | 0.663 (9) |
H13C | 0.758711 | 0.387889 | 0.170296 | 0.073* | 0.663 (9) |
C14 | 0.8909 (4) | 0.4015 (3) | 0.3353 (2) | 0.0435 (7)* | 0.663 (9) |
H14A | 0.910320 | 0.503380 | 0.337393 | 0.065* | 0.663 (9) |
H14B | 0.795749 | 0.387336 | 0.325245 | 0.065* | 0.663 (9) |
H14C | 0.940554 | 0.357500 | 0.389733 | 0.065* | 0.663 (9) |
C15 | 1.0755 (3) | 0.3641 (3) | 0.2819 (2) | 0.0496 (8)* | 0.663 (9) |
H15A | 1.090359 | 0.466948 | 0.285821 | 0.074* | 0.663 (9) |
H15B | 1.125448 | 0.319406 | 0.336004 | 0.074* | 0.663 (9) |
H15C | 1.105413 | 0.325613 | 0.235551 | 0.074* | 0.663 (9) |
C13A | 1.0743 (7) | 0.3428 (10) | 0.3146 (7) | 0.088 (3)* | 0.337 (9) |
H13D | 1.088217 | 0.297754 | 0.370414 | 0.132* | 0.337 (9) |
H13E | 1.127343 | 0.293692 | 0.283871 | 0.132* | 0.337 (9) |
H13F | 1.101335 | 0.442639 | 0.322782 | 0.132* | 0.337 (9) |
C14A | 0.9016 (9) | 0.3989 (6) | 0.1798 (3) | 0.0563 (16)* | 0.337 (9) |
H14D | 0.920339 | 0.500938 | 0.186074 | 0.084* | 0.337 (9) |
H14E | 0.956852 | 0.355127 | 0.148616 | 0.084* | 0.337 (9) |
H14F | 0.807893 | 0.384326 | 0.148001 | 0.084* | 0.337 (9) |
C15A | 0.8467 (7) | 0.3965 (5) | 0.3131 (4) | 0.0457 (14)* | 0.337 (9) |
H15D | 0.868380 | 0.351102 | 0.369345 | 0.069* | 0.337 (9) |
H15E | 0.863637 | 0.498739 | 0.320288 | 0.069* | 0.337 (9) |
H15F | 0.753021 | 0.380433 | 0.281860 | 0.069* | 0.337 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0710 (10) | 0.0648 (10) | 0.0455 (8) | 0.0213 (8) | 0.0162 (7) | 0.0058 (7) |
N2 | 0.0830 (11) | 0.0716 (10) | 0.0389 (7) | 0.0087 (9) | 0.0247 (7) | −0.0069 (7) |
N3 | 0.0652 (9) | 0.0656 (9) | 0.0338 (6) | 0.0110 (7) | 0.0155 (6) | 0.0044 (6) |
N4 | 0.0747 (10) | 0.0625 (10) | 0.0571 (9) | 0.0175 (8) | 0.0339 (8) | 0.0059 (7) |
C1 | 0.0545 (9) | 0.0407 (8) | 0.0379 (7) | 0.0050 (6) | 0.0166 (6) | −0.0010 (6) |
C2 | 0.0480 (7) | 0.0346 (6) | 0.0301 (6) | −0.0007 (5) | 0.0121 (5) | −0.0019 (5) |
C3 | 0.0543 (8) | 0.0401 (7) | 0.0368 (7) | 0.0020 (6) | 0.0160 (6) | −0.0050 (6) |
C4 | 0.0469 (7) | 0.0354 (6) | 0.0264 (5) | −0.0043 (5) | 0.0123 (5) | −0.0018 (5) |
C5 | 0.0501 (8) | 0.0398 (7) | 0.0273 (6) | 0.0012 (6) | 0.0120 (5) | −0.0001 (5) |
C6 | 0.0453 (7) | 0.0372 (7) | 0.0303 (6) | −0.0028 (5) | 0.0125 (5) | 0.0000 (5) |
C7 | 0.0468 (7) | 0.0407 (7) | 0.0286 (6) | 0.0004 (6) | 0.0128 (5) | −0.0003 (5) |
C8 | 0.0412 (7) | 0.0390 (7) | 0.0278 (6) | −0.0043 (5) | 0.0125 (5) | 0.0010 (5) |
C9 | 0.0402 (7) | 0.0416 (7) | 0.0292 (6) | −0.0010 (5) | 0.0138 (5) | 0.0011 (5) |
C10 | 0.0414 (7) | 0.0454 (8) | 0.0335 (6) | 0.0037 (6) | 0.0118 (5) | 0.0038 (5) |
C11 | 0.0491 (8) | 0.0486 (8) | 0.0353 (7) | 0.0024 (6) | 0.0179 (6) | 0.0043 (6) |
N5 | 0.0400 (6) | 0.0364 (6) | 0.0307 (5) | −0.0003 (4) | 0.0133 (4) | 0.0001 (4) |
C12 | 0.0688 (11) | 0.0371 (8) | 0.0521 (9) | −0.0016 (7) | 0.0243 (8) | 0.0000 (6) |
N1—C1 | 1.156 (2) | N5—C14A | 1.455 (5) |
N2—C3 | 1.1481 (19) | N5—C15A | 1.496 (5) |
N3—C10 | 1.1480 (18) | C12—H12A | 0.9800 |
N4—C11 | 1.148 (2) | C12—H12B | 0.9800 |
C1—C2 | 1.414 (2) | C12—H12C | 0.9800 |
C2—C3 | 1.4220 (19) | C13—H13A | 0.9800 |
C2—C4 | 1.3929 (19) | C13—H13B | 0.9800 |
C4—H4 | 0.9500 | C13—H13C | 0.9800 |
C4—C5 | 1.382 (2) | C14—H14A | 0.9800 |
C5—H5 | 0.9500 | C14—H14B | 0.9800 |
C5—C6 | 1.387 (2) | C14—H14C | 0.9800 |
C6—H6 | 0.9500 | C15—H15A | 0.9800 |
C6—C7 | 1.386 (2) | C15—H15B | 0.9800 |
C7—H7 | 0.9500 | C15—H15C | 0.9800 |
C7—C8 | 1.3832 (19) | C13A—H13D | 0.9800 |
C8—H8 | 0.9500 | C13A—H13E | 0.9800 |
C8—C9 | 1.3938 (19) | C13A—H13F | 0.9800 |
C9—C10 | 1.4225 (18) | C14A—H14D | 0.9800 |
C9—C11 | 1.422 (2) | C14A—H14E | 0.9800 |
N5—C12 | 1.4883 (19) | C14A—H14F | 0.9800 |
N5—C13 | 1.511 (3) | C15A—H15D | 0.9800 |
N5—C14 | 1.505 (3) | C15A—H15E | 0.9800 |
N5—C15 | 1.497 (3) | C15A—H15F | 0.9800 |
N5—C13A | 1.495 (7) | ||
N1—C1—C2 | 178.84 (17) | H12A—C12—H12B | 109.5 |
C1—C2—C3 | 118.35 (13) | H12A—C12—H12C | 109.5 |
C4—C2—C1 | 121.18 (12) | H12B—C12—H12C | 109.5 |
C4—C2—C3 | 120.45 (13) | N5—C13—H13A | 109.5 |
N2—C3—C2 | 176.64 (18) | N5—C13—H13B | 109.5 |
C2—C4—H4 | 117.4 | N5—C13—H13C | 109.5 |
C5—C4—C2 | 125.15 (12) | H13A—C13—H13B | 109.5 |
C5—C4—H4 | 117.4 | H13A—C13—H13C | 109.5 |
C4—C5—H5 | 117.6 | H13B—C13—H13C | 109.5 |
C4—C5—C6 | 124.74 (12) | N5—C14—H14A | 109.5 |
C6—C5—H5 | 117.6 | N5—C14—H14B | 109.5 |
C5—C6—H6 | 118.3 | N5—C14—H14C | 109.5 |
C7—C6—C5 | 123.32 (12) | H14A—C14—H14B | 109.5 |
C7—C6—H6 | 118.3 | H14A—C14—H14C | 109.5 |
C6—C7—H7 | 117.7 | H14B—C14—H14C | 109.5 |
C8—C7—C6 | 124.69 (12) | N5—C15—H15A | 109.5 |
C8—C7—H7 | 117.7 | N5—C15—H15B | 109.5 |
C7—C8—H8 | 117.9 | N5—C15—H15C | 109.5 |
C7—C8—C9 | 124.23 (12) | H15A—C15—H15B | 109.5 |
C9—C8—H8 | 117.9 | H15A—C15—H15C | 109.5 |
C8—C9—C10 | 119.98 (12) | H15B—C15—H15C | 109.5 |
C8—C9—C11 | 122.28 (12) | N5—C13A—H13D | 109.5 |
C11—C9—C10 | 117.69 (13) | N5—C13A—H13E | 109.5 |
N3—C10—C9 | 177.83 (16) | N5—C13A—H13F | 109.5 |
N4—C11—C9 | 179.3 (2) | H13D—C13A—H13E | 109.5 |
C12—N5—C13 | 109.12 (15) | H13D—C13A—H13F | 109.5 |
C12—N5—C14 | 112.07 (14) | H13E—C13A—H13F | 109.5 |
C12—N5—C15 | 111.28 (15) | N5—C14A—H14D | 109.5 |
C12—N5—C13A | 103.6 (4) | N5—C14A—H14E | 109.5 |
C12—N5—C15A | 106.9 (2) | N5—C14A—H14F | 109.5 |
C14—N5—C13 | 108.31 (17) | H14D—C14A—H14E | 109.5 |
C15—N5—C13 | 109.50 (18) | H14D—C14A—H14F | 109.5 |
C15—N5—C14 | 106.48 (17) | H14E—C14A—H14F | 109.5 |
C13A—N5—C15A | 110.5 (4) | N5—C15A—H15D | 109.5 |
C14A—N5—C12 | 111.3 (3) | N5—C15A—H15E | 109.5 |
C14A—N5—C13A | 113.0 (4) | N5—C15A—H15F | 109.5 |
C14A—N5—C15A | 111.2 (3) | H15D—C15A—H15E | 109.5 |
N5—C12—H12A | 109.5 | H15D—C15A—H15F | 109.5 |
N5—C12—H12B | 109.5 | H15E—C15A—H15F | 109.5 |
N5—C12—H12C | 109.5 | ||
C1—C2—C4—C5 | 179.67 (14) | C5—C6—C7—C8 | −176.78 (14) |
C2—C4—C5—C6 | −176.99 (14) | C6—C7—C8—C9 | 175.87 (14) |
C3—C2—C4—C5 | 1.4 (2) | C7—C8—C9—C10 | 0.6 (2) |
C4—C5—C6—C7 | 178.25 (14) | C7—C8—C9—C11 | −176.86 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···N3i | 0.95 | 2.58 | 3.4819 (18) | 159 |
C12—H12A···N2ii | 0.98 | 2.51 | 3.373 (2) | 147 |
Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) x+1/2, −y+1/2, z+1/2. |
Funding information
Funding for this research was provided by: National Science Foundation (grant No. DMR-1523611).
References
Bruker (2016). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2018). APEX3. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chetkina, L. A. & Bel'skii, V. K. (2002). Sov. Phys. Crystallogr. 47, 581–602. CAS Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Edmonds, J., Herdklotz, J. K. & Sass, R. L. (1970). Acta Cryst. B26, 1355–1362. CSD CrossRef IUCr Journals Google Scholar
Etemad, S. & Heeger, A. J. (1982). Annu. Rev. Phys. Chem. 33, 443–469. CrossRef CAS Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Jayamurugan, G., Finke, A. D., Gisselbrecht, J.-P., Boudon, C., Schweizer, W. B. & Diederich, F. (2014). J. Org. Chem. 79, 426–431. CSD CrossRef CAS PubMed Google Scholar
Marder, S. R., Gorman, C. B., Meyers, F., Perry, J. W., Bourhill, G., Brédas, J.-L. & Pierce, B. M. (1994). Science, 265, 632–635. CrossRef PubMed CAS Google Scholar
Meisner, J. S., Sedbrook, D. F., Krikorian, M., Chen, J., Sattler, A., Carnes, M. E., Murray, C. B., Steigerwald, M. & Nuckolls, C. (2012). Chem. Sci. 3, 1007–1014. CSD CrossRef CAS Google Scholar
Noerenberg, H., Kratzin, H., Boldt, P. & Sheldrick, W. S. (1977). Chem. Ber. 110, 1284–1293. CSD CrossRef CAS Google Scholar
Reck, G. & Dahne, L. (2006). Private Communication (refcode NEQHOH). CCDC, Cambridge, England. Google Scholar
Sass, R. L. & Nichols, T. D. (1974). Z. Kristallogr. Cryst. Mater. 140, 1–9. CrossRef CAS Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Tsuji, Y. & Hoffmann, R. (2016). Chem. Eur. J. 22, 4878–4888. CrossRef CAS PubMed Google Scholar
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