research communications
6-Chloro-1-phenylindoline-2,3-dione:
non-linear optical and charge-transport propertiesaState Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, Shandong Province, People's Republic of China, and bSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, Shandong Province, People's Republic of China
*Correspondence e-mail: fangqi@sdu.edu.cn
In the title compound, C14H8ClNO2, the dihedral angle between the isatin moiety (r.m.s. deviation = 0.014 Å) and the phenyl ring is 51.8 (1)°. All molecules have the same `frozen chiral' conformation in the non-centrosymmetric P212121 A polycrystalline sample of the title compound exhibits a considerable second-order (frequency doubling of 1064 nm light to output 532 nm light). In the crystal, molecules are linked by C—H⋯O hydrogen bonds, generating chains along the [100] direction. Based on a DFT calculation, [100] proves to be the most favourable direction for charge transport and the title crystal could be used as a hole-transport material because of its high hole mobility.
Keywords: crystal structure; absolute structure; isatin derivatives; frozen chiral conformation; SHG effect; charge-transport property.
CCDC reference: 1528555
1. Chemical context
Derivatives of isatin, also called indoline-2,3-dione, have drawn great attention for their biological and pharmacological properties such as anticonvulsant (Prakash et al., 2010), anticancer (Abadi et al., 2006) and anti-HIV (Bal et al., 2005) activities. The isatin skeleton can be found in analytical reagents, pesticides and dye intermediates. Isatin derivatives are also versatile precursors in the synthesis of a variety of However, the opto-electronic properties of isatin derivatives are rarely investigated.
The crystal structures of many isatin derivatives have been reported, among the analogues of the title compound are 6-bromo-1-butylindoline-2,3-dione (Ji et al., 2009), 1-ethyl-5-iodoindoline-2,3-dione (Wang et al., 2014), 6-chloroindoline-2,3-dione (Golen & Manke, 2016), 1-benzyl-5-fluoroindoline-2,3-dione (Sharmila et al., 2015) and 1-phenylindoline-2,3-dione (Shukla & Rajeswaran, 2011). The synthesis of the title compound was reported in 2014 (Bergman & Stensland, 2014). Recently, we prepared this compound by a different method, which involves the use of O2 in air as oxidant. Herein, we report the and some opto-electronic properties of this compound.
2. Structural commentary
As shown in Fig. 1, the isatin unit of the molecule is essentially planar, with a mean deviation of 0.009 (2) Å and a maximum deviation of 0.0870 (8) Å (for atom O1) from the mean plane of the indoline core (C1–C8/N1). As a result of the short intramolecular contacts (C10⋯C7, C14⋯O1) and the H7⋯H10 there is a dihedral angle of 51.8 (1)° between the phenyl ring and the mean plane of the indoline core. As a comparison, the dihedral angle of the DFT/b3lyp/6-311++g(2d,p) optimized (see below) title molecule is 60.0°. The sum of the angles surrounding N1 is 359.96°, suggesting that this atom is sp2 hybridized. The C9—N1 bond length [1.4279 (14) Å] is slightly shorter than that [1.436 (2) Å] in the similar compound 1-phenylindoline-2,3-dione (Shukla & Rajeswaran, 2011). The C1—C2 [1.557 (2) Å] bond length is longer than a typical Csp2—Csp2 bond but it is notable that the geometry optimization gave a length of 1.568 Å for this bond. The C1—C2 length [1.545 (3) Å] in 1-phenylindoline-2,3-dione is somewhat shorter (Shukla & Rajeswaran, 2011).
As a result of the P212121 of the crystal, all molecules have the same `frozen chiral' conformation (defined as conformation I). The single conformation of these molecules in this as-tested crystal is confirmed by a x = 0.03 (5) and R1 factor of 0.0317. By comparison, an inversion operation to the present structure resulted in an incorrect structure of conformation II with x = 0.97 (5) and R1 = 0.0336. 1-Phenylindoline-2,3-dione also crystallized in P212121 (Shukla & Rajeswaran, 2011) and this may be well suited to accommodate this class of molecules.
As shown in Figs. 1 and 2, the isoenergic conformations I and II are mirror images and non-superposable one another. The calculated rotation barrier (rotating around the N1—C9 bond to transform from I to II) is 8.74 kcal mol−1, which is much higher than the thermal energy kBT = 0.596 kcal mol−1 at 300 K. The main hindrance from may be the H7⋯H10 steric repulsion with a calculated distance of 1.759 Å at the transition state (see Fig. 2).
3. Supramolecular features
As shown in Fig. 3, the intermolecular interactions in the a-axis direction are characterized by a C10—H10⋯O1 hydrogen bond (Table 1) and an O1⋯H11(x − 1, y, z) [2.63 (2) Å] short contact between two side-by-side molecules. The strength of the hydrogen bond can be scaled by the electronic transfer integral (t) between two molecules and it was calculated by equation (3). The t value between the above two adjacent molecules is maximal (t1 = 0.196 eV), indicating that a kind of side-by-side one-dimensional chain has formed along the a-axis direction. We believe that this a-directional chain plays an important role in guiding the crystal growth, for the long axis of the bar-shaped crystal was indexed to be in the [100] direction.
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By the 21 [010] screw operation, molecules are packed into columns along the b-axis direction involving C2⋯C12(2 − x, + y, − z) [3.280 (2) Å] and H10⋯C14(2 − x, + y, − z) [2.50 (3) Å] short intermolecular contacts between two neighboring molecules (see Fig. 4). The transfer integral between such two face-to-face molecules is somewhat smaller (t2 = 0.116 eV) in this direction.
Along the c-axis direction, there is a H5⋯O2( + x, − y, 1 − z) [2.69 (2) Å] short intermolecular contact and the t value between the two molecules is a minimum (t3 = 0.0794 eV, see Fig. 4): thus the intermolecular interactions in this direction are relatively weak.
4. Calculation and opto-electronic properties
It is well known that the necessary structural condition for second-order non-linear optical response is non-centrosymmetry, both for molecules and crystals. The P212121 of the crystal prompted us to make a SHG (second harmonic generation) test. When the sample of crystalline powder was irradiated with infrared laser pulses (1064 nm), green light pulses (532 nm) could be observed.
Density functional theory (DFT) calculations for the electronic transfer integral t and the λ, were carried out using the GAUSSIAN03 program (Frisch et al., 2003) within the framework of b3lyp/6-311g(d).
The charge transport in organic semiconductors can be described by the hopping of an electron between a molecule and a neighbouring cation (hole) or anion shown below
Based on the Marcus electron-transfer theory (Marcus, 1993), the mobility (μ) in a one-dimensional uniform structure, can be expressed as (Sakanoue et al., 1999; Fang et al., 2015)
where d is the distance between two neighbouring molecules and λ is For the hole transport, λ can be expressed by (Berlin et al., 2003)
Thus, λ1 measures the energy difference between the stable molecule and the molecule with the cation geometry and λ2 measures the energy difference between the stable cation and the cation with the molecule geometry.
The t in equation (1) is the electronic transfer integral, which measures the intermolecular interactions between two neighbouring molecules and can be calculated by (Deng & Goddard, 2004)
where EHOMO and EHOMO-1 are the energy levels of the HOMO (highest occupied molecular orbital) and the HOMO-1 orbital of a two-molecule pair, respectively.
The molecular geometry for the t calculation is based on this X-ray structure without optimization, while the geometries of the molecule and the cation/anion have been optimized for the λ calculation. Since the molecule in the crystal is different from the free molecule, we adopted the cage model (Fang et al., 2015) in the course of geometry optimization, in which the host (molecule or cation or anion) being optimized is constrained by four guest molecules with fixed X-ray structures (see Fig. 5).
As shown in Table 2, (i) the hole mobility (μh) is one order of magnitude larger than the electron mobility (μe), indicating that the title crystal could be used as a hole-transport material rather than an electron-transport material and (ii) both the hole mobility (μh) and the electron mobility (μe) in the [100] direction (the side-by-side chain direction) are an order of magnitude larger than those in the [010] direction (the face-to-face column direction).
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In summary, the side-by-side hydrogen bonding in the one-dimensional chain in the [100] direction is stronger than the face-to-face π–π interactions in the [010] direction for this crystal, which relates to the non-linear optical and electronic transport properties of the crystal.
5. Database survey
A search in the Cambridge Structural Database (WebCSD, Version 1.1.2; last update November 2016), for indoline-2,3-dione derivatives gave 137 hits. Among them, there are nine hits for halogen 6-substituted indoline-2,3-dione derivatives and two hits which contain the
of the 1-phenylindoline-2,3-dione skeleton. There are four non-centrosymmetric structures and seven centrosymmetric structures among these eleven crystal structures.6. Synthesis and crystallization
We synthesized the title compound by the reaction of 6-chloroindoline-2-one and phenylboronic acid (see Fig. 6). 6-Chloroindoline-2-one (0.168 g, 1.00 mmol) was dissolved in DMF (18 ml). Then pyridine (0.05 mL), phenylboronic acid (0.244 g, 2.00 mmol) and Cu(OAc)2·H2O (0.197 g, 0.99 mmol) were sequentially added into the flask. The mixture was stirred for two h at room temperature in the presence of air. After filtration, the filtrate was poured into 100 ml water and extracted with dichloromethane. The organic phase was washed by water and dried by anhydrous Na2SO4. The crude product was purified by silica gel eluting with a mixture of petroleum ether:ethyl acetate (30:1) to obtain an orange solid (0.096 g, yield 37%). 1H NMR (400 MHz, CDCl3) δ 7.64 (d, J = 8.4 Hz, 1H), 7.59 (t, J = 7.6 Hz, 2H), 7.49 (t, J = 7.4 Hz, 1H), 7.40 (d, J = 7.2 Hz, 2H), 7.15 (dd, J = 8.0, 1.6 Hz, 1H), 6.89 (d, J = 1.6 Hz, 1H). As shown in Fig. 7, the 1H NMR signals of all protons of the compound are well separated and well characterized. Orange bar-shaped crystals were obtained by slow evaporation of a solution of the title compound in mixed solvents of dichloromethane and n-hexane.
7. Refinement
Crystal data, diffraction data and structure . All hydrogen atoms were located from the difference-electron-density maps and refined freely, resulting in C—H lengths ranging from 0.92 (2) to 1.00 (2) Å.
details are summarized in Table 3Supporting information
CCDC reference: 1528555
https://doi.org/10.1107/S2056989017007630/hb7661sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017007630/hb7661Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989017007630/hb7661Isup3.cml
Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C14H8ClNO2 | Dx = 1.497 Mg m−3 |
Mr = 257.66 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 9992 reflections |
a = 6.8190 (3) Å | θ = 2.8–31.0° |
b = 7.7062 (3) Å | µ = 0.33 mm−1 |
c = 21.7492 (9) Å | T = 294 K |
V = 1142.89 (8) Å3 | Bar, orange |
Z = 4 | 0.58 × 0.24 × 0.18 mm |
F(000) = 528 |
Bruker APEXII CCD diffractometer | 3784 independent reflections |
Radiation source: fine-focus sealed tube | 3513 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
Detector resolution: 8.3 pixels mm-1 | θmax = 31.8°, θmin = 1.9° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −10→11 |
Tmin = 0.834, Tmax = 0.943 | l = −32→28 |
21380 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0575P)2 + 0.0865P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3784 reflections | Δρmax = 0.21 e Å−3 |
191 parameters | Δρmin = −0.23 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1583 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.03 (5) |
Experimental. Scan width 0.5° ω , Crystal to detector distance 5.96 cm, exposure time 15s, 10 hours and 36 minutes for data collection, with scale. 6-run at 2theta equal -28, -28, -35,-36,-36,-38, respectively. |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 1.36000 (5) | 0.40110 (5) | 0.561115 (17) | 0.05229 (11) | |
C7 | 1.10733 (16) | 0.54301 (15) | 0.64149 (5) | 0.0323 (2) | |
O2 | 0.48463 (15) | 0.81725 (15) | 0.61436 (5) | 0.0514 (3) | |
O1 | 0.58784 (14) | 0.83661 (15) | 0.74488 (5) | 0.0466 (2) | |
C5 | 1.0114 (2) | 0.5438 (2) | 0.53283 (6) | 0.0423 (3) | |
C6 | 1.14176 (18) | 0.50392 (15) | 0.57981 (5) | 0.0355 (2) | |
C8 | 0.93314 (16) | 0.62745 (14) | 0.65401 (5) | 0.0298 (2) | |
N1 | 0.86151 (14) | 0.68187 (13) | 0.71209 (4) | 0.03287 (18) | |
C9 | 0.95746 (17) | 0.65986 (15) | 0.76993 (5) | 0.0309 (2) | |
C14 | 0.8529 (2) | 0.58710 (17) | 0.81830 (6) | 0.0400 (3) | |
C13 | 0.9437 (3) | 0.5724 (2) | 0.87499 (6) | 0.0502 (3) | |
H13 | 0.8757 | 0.5247 | 0.9080 | 0.060* | |
C12 | 1.1351 (3) | 0.6281 (2) | 0.88297 (6) | 0.0539 (4) | |
C3 | 0.79945 (17) | 0.66972 (16) | 0.60753 (5) | 0.0339 (2) | |
C4 | 0.8377 (2) | 0.62747 (18) | 0.54664 (6) | 0.0417 (3) | |
C2 | 0.63341 (17) | 0.75880 (16) | 0.63578 (6) | 0.0366 (2) | |
C1 | 0.68398 (16) | 0.76703 (16) | 0.70553 (6) | 0.0348 (2) | |
C11 | 1.2390 (2) | 0.6983 (2) | 0.83442 (6) | 0.0456 (3) | |
C10 | 1.15006 (18) | 0.71514 (15) | 0.77716 (5) | 0.0350 (2) | |
H5 | 1.042 (3) | 0.510 (2) | 0.4916 (9) | 0.056 (5)* | |
H4 | 0.739 (3) | 0.659 (2) | 0.5147 (9) | 0.050 (5)* | |
H10 | 1.219 (3) | 0.768 (2) | 0.7437 (8) | 0.041 (4)* | |
H11 | 1.369 (3) | 0.735 (2) | 0.8379 (9) | 0.054 (5)* | |
H12 | 1.195 (4) | 0.618 (3) | 0.9210 (11) | 0.081 (7)* | |
H14 | 0.724 (3) | 0.548 (3) | 0.8112 (9) | 0.056 (5)* | |
H7 | 1.195 (3) | 0.509 (2) | 0.6711 (8) | 0.038 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.04536 (17) | 0.0669 (2) | 0.04463 (17) | 0.01248 (15) | 0.01136 (13) | −0.00487 (15) |
C7 | 0.0316 (5) | 0.0373 (5) | 0.0281 (4) | 0.0001 (4) | 0.0017 (4) | 0.0021 (4) |
O2 | 0.0373 (4) | 0.0633 (6) | 0.0536 (6) | 0.0104 (4) | −0.0091 (4) | −0.0017 (5) |
O1 | 0.0361 (4) | 0.0589 (6) | 0.0448 (5) | 0.0057 (4) | 0.0071 (4) | −0.0055 (4) |
C5 | 0.0491 (7) | 0.0514 (7) | 0.0263 (5) | 0.0011 (5) | 0.0025 (4) | −0.0016 (5) |
C6 | 0.0352 (5) | 0.0391 (5) | 0.0324 (5) | 0.0011 (4) | 0.0071 (4) | −0.0003 (4) |
C8 | 0.0299 (4) | 0.0330 (5) | 0.0265 (4) | −0.0031 (4) | 0.0022 (3) | 0.0008 (4) |
N1 | 0.0281 (4) | 0.0435 (5) | 0.0270 (4) | 0.0015 (4) | 0.0026 (3) | −0.0012 (3) |
C9 | 0.0354 (5) | 0.0315 (5) | 0.0260 (4) | 0.0013 (4) | 0.0026 (4) | −0.0002 (4) |
C14 | 0.0468 (7) | 0.0381 (5) | 0.0353 (5) | −0.0017 (5) | 0.0102 (5) | 0.0016 (4) |
C13 | 0.0712 (9) | 0.0490 (7) | 0.0305 (6) | 0.0122 (7) | 0.0121 (6) | 0.0080 (5) |
C12 | 0.0714 (9) | 0.0600 (8) | 0.0303 (5) | 0.0256 (8) | −0.0083 (6) | −0.0015 (5) |
C3 | 0.0328 (5) | 0.0384 (5) | 0.0305 (5) | −0.0006 (4) | −0.0017 (4) | 0.0013 (4) |
C4 | 0.0463 (6) | 0.0490 (6) | 0.0299 (5) | 0.0021 (5) | −0.0053 (5) | 0.0005 (5) |
C2 | 0.0313 (5) | 0.0400 (5) | 0.0385 (5) | −0.0019 (4) | −0.0019 (4) | 0.0001 (4) |
C1 | 0.0280 (5) | 0.0393 (5) | 0.0372 (5) | −0.0014 (4) | 0.0017 (4) | −0.0001 (4) |
C11 | 0.0453 (7) | 0.0527 (7) | 0.0388 (6) | 0.0106 (6) | −0.0109 (5) | −0.0067 (6) |
C10 | 0.0343 (5) | 0.0381 (5) | 0.0327 (5) | 0.0017 (4) | −0.0004 (4) | −0.0005 (4) |
Cl1—C6 | 1.7343 (12) | C9—C10 | 1.3896 (16) |
C7—C8 | 1.3815 (16) | C14—C13 | 1.384 (2) |
C7—C6 | 1.3948 (15) | C14—H14 | 0.94 (2) |
C7—H7 | 0.916 (17) | C13—C12 | 1.385 (3) |
O2—C2 | 1.2039 (16) | C13—H13 | 0.9300 |
O1—C1 | 1.2040 (15) | C12—C11 | 1.382 (2) |
C5—C4 | 1.3816 (19) | C12—H12 | 0.93 (2) |
C5—C6 | 1.3889 (18) | C3—C4 | 1.3884 (17) |
C5—H5 | 0.96 (2) | C3—C2 | 1.4597 (17) |
C8—C3 | 1.3996 (15) | C4—H4 | 1.00 (2) |
C8—N1 | 1.4179 (13) | C2—C1 | 1.5570 (17) |
N1—C1 | 1.3844 (14) | C11—C10 | 1.3916 (17) |
N1—C9 | 1.4279 (14) | C11—H11 | 0.93 (2) |
C9—C14 | 1.3892 (16) | C10—H10 | 0.956 (17) |
C8—C7—C6 | 115.85 (11) | C12—C13—H13 | 119.7 |
C8—C7—H7 | 123.8 (11) | C11—C12—C13 | 120.60 (13) |
C6—C7—H7 | 120.3 (11) | C11—C12—H12 | 119.1 (16) |
C4—C5—C6 | 119.46 (11) | C13—C12—H12 | 120.3 (16) |
C4—C5—H5 | 121.2 (12) | C4—C3—C8 | 120.79 (11) |
C6—C5—H5 | 119.3 (12) | C4—C3—C2 | 131.11 (11) |
C5—C6—C7 | 123.52 (11) | C8—C3—C2 | 108.10 (10) |
C5—C6—Cl1 | 118.54 (9) | C5—C4—C3 | 118.56 (11) |
C7—C6—Cl1 | 117.94 (10) | C5—C4—H4 | 122.6 (11) |
C7—C8—C3 | 121.83 (10) | C3—C4—H4 | 118.8 (11) |
C7—C8—N1 | 127.67 (10) | O2—C2—C3 | 131.81 (12) |
C3—C8—N1 | 110.50 (10) | O2—C2—C1 | 123.27 (12) |
C1—N1—C8 | 110.46 (9) | C3—C2—C1 | 104.92 (10) |
C1—N1—C9 | 123.21 (9) | O1—C1—N1 | 127.88 (12) |
C8—N1—C9 | 126.29 (9) | O1—C1—C2 | 126.16 (11) |
C14—C9—C10 | 121.55 (11) | N1—C1—C2 | 105.95 (10) |
C14—C9—N1 | 118.68 (11) | C12—C11—C10 | 119.78 (14) |
C10—C9—N1 | 119.75 (10) | C12—C11—H11 | 122.9 (12) |
C13—C14—C9 | 118.54 (14) | C10—C11—H11 | 117.3 (12) |
C13—C14—H14 | 122.6 (12) | C9—C10—C11 | 119.00 (12) |
C9—C14—H14 | 118.8 (12) | C9—C10—H10 | 120.5 (10) |
C14—C13—C12 | 120.52 (13) | C11—C10—H10 | 120.5 (11) |
C14—C13—H13 | 119.7 | ||
C4—C5—C6—C7 | 0.4 (2) | N1—C8—C3—C2 | 1.03 (13) |
C4—C5—C6—Cl1 | −179.26 (11) | C6—C5—C4—C3 | 0.2 (2) |
C8—C7—C6—C5 | −0.69 (19) | C8—C3—C4—C5 | −0.45 (19) |
C8—C7—C6—Cl1 | 178.95 (8) | C2—C3—C4—C5 | 178.98 (13) |
C6—C7—C8—C3 | 0.44 (17) | C4—C3—C2—O2 | 1.2 (2) |
C6—C7—C8—N1 | 179.89 (11) | C8—C3—C2—O2 | −179.36 (14) |
C7—C8—N1—C1 | 178.11 (11) | C4—C3—C2—C1 | −178.96 (13) |
C3—C8—N1—C1 | −2.38 (13) | C8—C3—C2—C1 | 0.52 (13) |
C7—C8—N1—C9 | 0.14 (18) | C8—N1—C1—O1 | −176.24 (13) |
C3—C8—N1—C9 | 179.64 (11) | C9—N1—C1—O1 | 1.80 (19) |
C1—N1—C9—C14 | 52.94 (16) | C8—N1—C1—C2 | 2.58 (12) |
C8—N1—C9—C14 | −129.33 (12) | C9—N1—C1—C2 | −179.37 (10) |
C1—N1—C9—C10 | −125.42 (12) | O2—C2—C1—O1 | −3.1 (2) |
C8—N1—C9—C10 | 52.31 (16) | C3—C2—C1—O1 | 176.95 (12) |
C10—C9—C14—C13 | 0.92 (19) | O2—C2—C1—N1 | 178.00 (12) |
N1—C9—C14—C13 | −177.41 (11) | C3—C2—C1—N1 | −1.90 (12) |
C9—C14—C13—C12 | −0.4 (2) | C13—C12—C11—C10 | 0.8 (2) |
C14—C13—C12—C11 | −0.4 (2) | C14—C9—C10—C11 | −0.56 (18) |
C7—C8—C3—C4 | 0.11 (18) | N1—C9—C10—C11 | 177.75 (11) |
N1—C8—C3—C4 | −179.42 (11) | C12—C11—C10—C9 | −0.30 (19) |
C7—C8—C3—C2 | −179.43 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O1i | 0.956 (17) | 2.572 (18) | 3.2063 (16) | 124.0 (13) |
Symmetry code: (i) x+1, y, z. |
t | λh (λe) | µh (µe) | |
side-by-side [100] | 0.196 | 0.319 (0.520) | 4.67 (0.524) |
face-to-face [010] | 0.116 | 0.319 (0.520) | 0.518 (0.058) |
Funding information
Funding for this research was provided by: National Natural Science Foundation of Chinahttps://doi.org/10.13039/501100001809 (award Nos. 21472116, 20972089); Key Laboratory of Crystal Materials.
References
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