organic compounds
11,11-Diphenyl-11H-indeno[1,2-b]quinoxaline
aSchool of Biology and Environment, Nanjing Polytechnic Institute, Nanjing 210048, People's Republic of China, and bTargeted MRI Contrast Agents Laboratory of Jiangsu Province, Nanjing Polytechnic Institute, Nanjing 210048, People's Republic of China
*Correspondence e-mail: njutshs@126.com
In the title compound, C27H18N2, the mean planes of the pendant benzene rings are approximately perpendicular to one another, making a dihedral angle of 79.3 (5)°; the indeno[1,2-b]quinoxaline ring system (r.m.s. deviation = 0.1197 Å) is twisted with respect to the pendant benzene rings by 70.0 (4) and 67.6 (3)°. Weak aromatic π–π stacking [centroid–centroid separation = 3.628 (2) Å] and C—H⋯π interactions occur in the crystal.
Keywords: crystal structure; indene; quinoxaline; indeno[1,2-b]quinoxaline.
CCDC reference: 2026803
Structure description
Some quinoxaline-based N-heteroacenes show a narrow band-gap, high thermal stability and aligned film morphology, which can be applied as the hole transport layers in quantum dot light-emitting diodes (QLEDs) (Bai et al., 2015). As part of our work in this area, we now report the synthesis and of the title indeno[1,2-b]quinoxaline derivative.
The molecular structure of the title compound is shown in Fig. 1. The pendant C1–C6 and C8–C13 benzene rings are nearly perpendicular to one another [dihedral angle = 79.3 (5)°] while the indeno[1,2-b]quinoxaline fused ring system (N1–N2/C7,C14–C27) is twisted with respect to the C1–C6 and C8–C13 benzene rings, subtending dihedral angles of 70.0 (4) and 67.6 (3)°, respectively.
In the crystal, weak Cg6⋯Cg6i aromatic π–π stacking interactions [centroid–centroid separation = 3.628 (2), slippage = 1.717 Å, symmetry code: (i) = 1 − x, 1 − y, 1 − z; where Cg6 is the centroid of the C22–C27 benzene ring] link the molecules into inversion dimers and weak C—H⋯π interactions link the dimers (Table 1, Fig. 2).
Synthesis and crystallization
The title compound was prepared in three steps. In the first step, a mixture of 1H-indene-1,2,3-trione (3.20 g, 20 mmol) and benzene-1,2-diamine (2.16 g, 20 mmol) in ethanol (100 ml) was heated to reflux under stirring for 5 h. 11H-Indeno[1,2-b]quinoxalin-11-one (1) was obtained as yellow powder by filtering after cooling. Then, a solution of compound 1 (2.32 g, 10 mmol) in THF (30 ml) was added dropwise into a solution of phenylmagnesium bromide (2.17 g, 12 mmol) in THF (30 ml). The mixture was heated to reflux with stirring for 12 h. This reaction was quenched by a of NH4Cl and the intermediate 11-phenyl-11H-indeno[1,2-b]quinoxalin-11-ol (2) was obtained by flash In the last step, trifluoroacetic acid (7 ml) was added dropwise to a solution of compound 2 (0.58 g, 2.50 mmol) in benzene (3 ml) and the mixture was heated at 50°C for 12 h. Then, the reaction mixture was transferred to an ice bath and NaOH was used to increase the pH of the solution to 10. After the reaction, DCM was used to extract the product and Na2SO4 was used as desiccant. The crude product was purified by flash to obtain a yellow powder product of the title compound. The total yield was about 15%. Single crystals of the title compound suitable for X-ray data collection were obtained by the slow evaporation of a methanol solution.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 2026803
https://doi.org/10.1107/S2414314620012134/hb4357sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620012134/hb4357Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314620012134/hb4357Isup3.cml
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).C27H18N2 | F(000) = 776 |
Mr = 370.43 | Dx = 1.289 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.642 (5) Å | Cell parameters from 3937 reflections |
b = 11.407 (5) Å | θ = 2.4–27.4° |
c = 17.858 (8) Å | µ = 0.08 mm−1 |
β = 103.606 (5)° | T = 296 K |
V = 1909.0 (16) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.20 × 0.10 mm |
Bruker APEXII CCD diffractometer | 3277 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω scans | θmax = 27.6°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −12→12 |
Tmin = 0.859, Tmax = 1.000 | k = −14→14 |
11621 measured reflections | l = −23→18 |
4429 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0447P)2 + 0.3316P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
4429 reflections | Δρmax = 0.15 e Å−3 |
262 parameters | Δρmin = −0.20 e Å−3 |
0 restraints |
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. H atoms were placed geometrically (C—H = 0.93 Å) and refined as riding atoms with Uiso(H) = 1.2Ueq(C). |
x | y | z | Uiso*/Ueq | ||
N1 | 0.51226 (11) | 0.55738 (9) | 0.65772 (6) | 0.0394 (3) | |
N2 | 0.23762 (11) | 0.47436 (9) | 0.57474 (6) | 0.0395 (3) | |
C1 | 0.5462 (2) | 1.01277 (15) | 0.63861 (11) | 0.0695 (5) | |
H1 | 0.5840 | 1.0786 | 0.6200 | 0.083* | |
C2 | 0.4016 (2) | 0.99914 (15) | 0.62609 (11) | 0.0716 (5) | |
H2 | 0.3410 | 1.0565 | 0.5995 | 0.086* | |
C3 | 0.34490 (17) | 0.90057 (13) | 0.65275 (9) | 0.0541 (4) | |
H3 | 0.2464 | 0.8923 | 0.6439 | 0.065* | |
C4 | 0.43262 (13) | 0.81433 (11) | 0.69233 (7) | 0.0375 (3) | |
C5 | 0.57958 (15) | 0.83006 (12) | 0.70533 (9) | 0.0495 (3) | |
H5 | 0.6409 | 0.7734 | 0.7322 | 0.059* | |
C6 | 0.63502 (18) | 0.92863 (14) | 0.67879 (11) | 0.0631 (4) | |
H6 | 0.7334 | 0.9382 | 0.6882 | 0.076* | |
C7 | 0.37522 (12) | 0.70131 (11) | 0.72101 (7) | 0.0350 (3) | |
C8 | 0.44723 (13) | 0.67853 (11) | 0.80551 (7) | 0.0382 (3) | |
C9 | 0.45826 (15) | 0.76998 (14) | 0.85801 (8) | 0.0495 (3) | |
H9 | 0.4275 | 0.8445 | 0.8405 | 0.059* | |
C10 | 0.51424 (17) | 0.75184 (17) | 0.93576 (9) | 0.0620 (4) | |
H10 | 0.5191 | 0.8135 | 0.9704 | 0.074* | |
C11 | 0.56268 (18) | 0.64278 (19) | 0.96174 (10) | 0.0707 (5) | |
H11 | 0.6005 | 0.6304 | 1.0140 | 0.085* | |
C12 | 0.55541 (18) | 0.55199 (17) | 0.91067 (10) | 0.0667 (5) | |
H12 | 0.5904 | 0.4786 | 0.9284 | 0.080* | |
C13 | 0.49617 (15) | 0.56892 (13) | 0.83284 (9) | 0.0504 (4) | |
H13 | 0.4893 | 0.5063 | 0.7988 | 0.060* | |
C14 | 0.21179 (13) | 0.70151 (11) | 0.70965 (7) | 0.0363 (3) | |
C15 | 0.12920 (14) | 0.76476 (12) | 0.74945 (8) | 0.0450 (3) | |
H15 | 0.1717 | 0.8172 | 0.7879 | 0.054* | |
C16 | −0.01721 (15) | 0.74878 (13) | 0.73120 (9) | 0.0486 (3) | |
H16 | −0.0727 | 0.7907 | 0.7580 | 0.058* | |
C17 | −0.08276 (14) | 0.67165 (13) | 0.67389 (9) | 0.0486 (3) | |
H17 | −0.1814 | 0.6630 | 0.6622 | 0.058* | |
C18 | −0.00211 (14) | 0.60742 (12) | 0.63394 (8) | 0.0434 (3) | |
H18 | −0.0454 | 0.5555 | 0.5953 | 0.052* | |
C19 | 0.14523 (13) | 0.62214 (11) | 0.65281 (7) | 0.0358 (3) | |
C20 | 0.25545 (13) | 0.55958 (10) | 0.62526 (7) | 0.0345 (3) | |
C21 | 0.39212 (13) | 0.60103 (10) | 0.66650 (7) | 0.0345 (3) | |
C22 | 0.49792 (14) | 0.46536 (11) | 0.60637 (7) | 0.0382 (3) | |
C23 | 0.36232 (14) | 0.42444 (11) | 0.56559 (7) | 0.0378 (3) | |
C24 | 0.35458 (17) | 0.32749 (12) | 0.51582 (8) | 0.0483 (3) | |
H24 | 0.2661 | 0.2993 | 0.4894 | 0.058* | |
C25 | 0.47617 (18) | 0.27492 (13) | 0.50633 (9) | 0.0547 (4) | |
H25 | 0.4701 | 0.2115 | 0.4730 | 0.066* | |
C26 | 0.61001 (17) | 0.31559 (13) | 0.54628 (9) | 0.0547 (4) | |
H26 | 0.6921 | 0.2787 | 0.5394 | 0.066* | |
C27 | 0.62156 (15) | 0.40861 (12) | 0.59517 (9) | 0.0481 (3) | |
H27 | 0.7112 | 0.4348 | 0.6213 | 0.058* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0374 (6) | 0.0388 (6) | 0.0444 (6) | 0.0031 (5) | 0.0144 (5) | 0.0002 (5) |
N2 | 0.0425 (6) | 0.0388 (6) | 0.0375 (6) | 0.0012 (5) | 0.0099 (5) | −0.0035 (5) |
C1 | 0.0864 (13) | 0.0474 (9) | 0.0773 (12) | −0.0137 (9) | 0.0241 (10) | 0.0124 (9) |
C2 | 0.0785 (12) | 0.0502 (9) | 0.0802 (13) | 0.0038 (9) | 0.0069 (10) | 0.0227 (9) |
C3 | 0.0501 (8) | 0.0495 (8) | 0.0577 (9) | 0.0020 (7) | 0.0027 (7) | 0.0076 (7) |
C4 | 0.0425 (7) | 0.0346 (6) | 0.0354 (7) | 0.0000 (5) | 0.0093 (5) | −0.0031 (5) |
C5 | 0.0438 (8) | 0.0458 (8) | 0.0601 (9) | 0.0000 (6) | 0.0143 (7) | 0.0061 (7) |
C6 | 0.0559 (9) | 0.0569 (10) | 0.0786 (12) | −0.0120 (8) | 0.0201 (8) | 0.0063 (9) |
C7 | 0.0323 (6) | 0.0350 (6) | 0.0380 (7) | 0.0017 (5) | 0.0088 (5) | −0.0035 (5) |
C8 | 0.0323 (6) | 0.0451 (7) | 0.0379 (7) | −0.0007 (5) | 0.0097 (5) | 0.0017 (6) |
C9 | 0.0470 (8) | 0.0578 (9) | 0.0422 (8) | 0.0025 (7) | 0.0076 (6) | −0.0065 (7) |
C10 | 0.0554 (9) | 0.0887 (13) | 0.0408 (9) | −0.0076 (9) | 0.0087 (7) | −0.0100 (8) |
C11 | 0.0606 (10) | 0.1086 (15) | 0.0401 (9) | −0.0102 (10) | 0.0062 (7) | 0.0181 (10) |
C12 | 0.0644 (11) | 0.0752 (12) | 0.0589 (11) | 0.0029 (9) | 0.0113 (8) | 0.0293 (9) |
C13 | 0.0507 (8) | 0.0505 (8) | 0.0513 (9) | 0.0006 (7) | 0.0146 (7) | 0.0102 (7) |
C14 | 0.0349 (6) | 0.0364 (6) | 0.0381 (7) | 0.0029 (5) | 0.0095 (5) | 0.0006 (5) |
C15 | 0.0424 (7) | 0.0459 (7) | 0.0473 (8) | 0.0032 (6) | 0.0116 (6) | −0.0110 (6) |
C16 | 0.0426 (7) | 0.0523 (8) | 0.0544 (9) | 0.0082 (6) | 0.0183 (6) | −0.0072 (7) |
C17 | 0.0327 (7) | 0.0566 (8) | 0.0568 (9) | 0.0031 (6) | 0.0108 (6) | −0.0035 (7) |
C18 | 0.0368 (7) | 0.0460 (7) | 0.0460 (8) | 0.0004 (6) | 0.0068 (6) | −0.0057 (6) |
C19 | 0.0350 (6) | 0.0361 (6) | 0.0365 (7) | 0.0025 (5) | 0.0088 (5) | 0.0001 (5) |
C20 | 0.0363 (6) | 0.0336 (6) | 0.0341 (7) | 0.0010 (5) | 0.0093 (5) | 0.0012 (5) |
C21 | 0.0368 (6) | 0.0324 (6) | 0.0357 (6) | 0.0013 (5) | 0.0114 (5) | 0.0015 (5) |
C22 | 0.0446 (7) | 0.0339 (6) | 0.0398 (7) | 0.0043 (5) | 0.0174 (6) | 0.0052 (5) |
C23 | 0.0465 (7) | 0.0356 (6) | 0.0335 (7) | 0.0049 (5) | 0.0137 (5) | 0.0031 (5) |
C24 | 0.0601 (9) | 0.0433 (7) | 0.0426 (8) | 0.0030 (6) | 0.0143 (6) | −0.0052 (6) |
C25 | 0.0788 (11) | 0.0408 (8) | 0.0509 (9) | 0.0103 (7) | 0.0278 (8) | −0.0044 (7) |
C26 | 0.0614 (9) | 0.0458 (8) | 0.0657 (10) | 0.0147 (7) | 0.0324 (8) | 0.0033 (7) |
C27 | 0.0457 (8) | 0.0454 (8) | 0.0582 (9) | 0.0069 (6) | 0.0225 (7) | 0.0040 (7) |
N1—C21 | 1.3038 (16) | C11—C12 | 1.371 (3) |
N1—C22 | 1.3791 (17) | C12—H12 | 0.9300 |
N2—C20 | 1.3099 (16) | C12—C13 | 1.386 (2) |
N2—C23 | 1.3744 (17) | C13—H13 | 0.9300 |
C1—H1 | 0.9300 | C14—C15 | 1.3878 (18) |
C1—C2 | 1.368 (3) | C14—C19 | 1.3984 (18) |
C1—C6 | 1.371 (2) | C15—H15 | 0.9300 |
C2—H2 | 0.9300 | C15—C16 | 1.384 (2) |
C2—C3 | 1.383 (2) | C16—H16 | 0.9300 |
C3—H3 | 0.9300 | C16—C17 | 1.384 (2) |
C3—C4 | 1.3790 (19) | C17—H17 | 0.9300 |
C4—C5 | 1.3925 (19) | C17—C18 | 1.3826 (19) |
C4—C7 | 1.5375 (18) | C18—H18 | 0.9300 |
C5—H5 | 0.9300 | C18—C19 | 1.3909 (19) |
C5—C6 | 1.376 (2) | C19—C20 | 1.4583 (17) |
C6—H6 | 0.9300 | C20—C21 | 1.4303 (18) |
C7—C8 | 1.5276 (19) | C22—C23 | 1.4176 (19) |
C7—C14 | 1.5408 (18) | C22—C27 | 1.4116 (18) |
C7—C21 | 1.5353 (17) | C23—C24 | 1.4097 (18) |
C8—C9 | 1.390 (2) | C24—H24 | 0.9300 |
C8—C13 | 1.384 (2) | C24—C25 | 1.362 (2) |
C9—H9 | 0.9300 | C25—H25 | 0.9300 |
C9—C10 | 1.382 (2) | C25—C26 | 1.399 (2) |
C10—H10 | 0.9300 | C26—H26 | 0.9300 |
C10—C11 | 1.371 (3) | C26—C27 | 1.362 (2) |
C11—H11 | 0.9300 | C27—H27 | 0.9300 |
C21—N1—C22 | 114.68 (11) | C12—C13—H13 | 119.8 |
C20—N2—C23 | 114.37 (11) | C15—C14—C7 | 128.73 (12) |
C2—C1—H1 | 120.2 | C15—C14—C19 | 119.19 (12) |
C2—C1—C6 | 119.53 (15) | C19—C14—C7 | 112.03 (10) |
C6—C1—H1 | 120.2 | C14—C15—H15 | 120.4 |
C1—C2—H2 | 119.8 | C16—C15—C14 | 119.16 (13) |
C1—C2—C3 | 120.42 (16) | C16—C15—H15 | 120.4 |
C3—C2—H2 | 119.8 | C15—C16—H16 | 119.3 |
C2—C3—H3 | 119.6 | C15—C16—C17 | 121.38 (12) |
C4—C3—C2 | 120.81 (15) | C17—C16—H16 | 119.3 |
C4—C3—H3 | 119.6 | C16—C17—H17 | 119.9 |
C3—C4—C5 | 118.09 (13) | C18—C17—C16 | 120.25 (13) |
C3—C4—C7 | 122.92 (12) | C18—C17—H17 | 119.9 |
C5—C4—C7 | 118.97 (11) | C17—C18—H18 | 120.7 |
C4—C5—H5 | 119.7 | C17—C18—C19 | 118.52 (13) |
C6—C5—C4 | 120.69 (14) | C19—C18—H18 | 120.7 |
C6—C5—H5 | 119.7 | C14—C19—C20 | 108.37 (11) |
C1—C6—C5 | 120.45 (16) | C18—C19—C14 | 121.48 (11) |
C1—C6—H6 | 119.8 | C18—C19—C20 | 130.03 (12) |
C5—C6—H6 | 119.8 | N2—C20—C19 | 127.41 (11) |
C4—C7—C14 | 113.08 (10) | N2—C20—C21 | 123.76 (11) |
C8—C7—C4 | 110.86 (10) | C21—C20—C19 | 108.72 (11) |
C8—C7—C14 | 110.09 (10) | N1—C21—C7 | 126.20 (11) |
C8—C7—C21 | 114.09 (10) | N1—C21—C20 | 123.29 (12) |
C21—C7—C4 | 108.26 (10) | C20—C21—C7 | 110.51 (10) |
C21—C7—C14 | 100.11 (9) | N1—C22—C23 | 121.89 (11) |
C9—C8—C7 | 118.92 (12) | N1—C22—C27 | 119.16 (12) |
C13—C8—C7 | 122.69 (12) | C27—C22—C23 | 118.94 (13) |
C13—C8—C9 | 118.32 (13) | N2—C23—C22 | 121.97 (12) |
C8—C9—H9 | 119.5 | N2—C23—C24 | 118.80 (12) |
C10—C9—C8 | 121.01 (15) | C24—C23—C22 | 119.20 (12) |
C10—C9—H9 | 119.5 | C23—C24—H24 | 119.9 |
C9—C10—H10 | 120.1 | C25—C24—C23 | 120.28 (14) |
C11—C10—C9 | 119.83 (16) | C25—C24—H24 | 119.9 |
C11—C10—H10 | 120.1 | C24—C25—H25 | 119.7 |
C10—C11—H11 | 120.0 | C24—C25—C26 | 120.55 (14) |
C10—C11—C12 | 120.03 (16) | C26—C25—H25 | 119.7 |
C12—C11—H11 | 120.0 | C25—C26—H26 | 119.6 |
C11—C12—H12 | 119.8 | C27—C26—C25 | 120.79 (14) |
C11—C12—C13 | 120.41 (16) | C27—C26—H26 | 119.6 |
C13—C12—H12 | 119.8 | C22—C27—H27 | 119.9 |
C8—C13—C12 | 120.35 (15) | C26—C27—C22 | 120.24 (14) |
C8—C13—H13 | 119.8 | C26—C27—H27 | 119.9 |
C6—C1—C2—C3 | −0.9 (3) | C17—C18—C19—C14 | −1.3 (2) |
C1—C2—C3—C4 | 0.0 (3) | C17—C18—C19—C20 | 174.12 (13) |
C2—C3—C4—C5 | 0.7 (2) | C15—C14—C19—C18 | 1.67 (19) |
C2—C3—C4—C7 | −178.05 (15) | C7—C14—C19—C18 | 179.30 (11) |
C3—C4—C5—C6 | −0.5 (2) | C15—C14—C19—C20 | −174.64 (11) |
C7—C4—C5—C6 | 178.31 (14) | C7—C14—C19—C20 | 2.99 (14) |
C2—C1—C6—C5 | 1.1 (3) | C23—N2—C20—C21 | 1.74 (17) |
C4—C5—C6—C1 | −0.4 (3) | C23—N2—C20—C19 | −173.95 (11) |
C3—C4—C7—C8 | −131.10 (13) | C18—C19—C20—N2 | 0.7 (2) |
C5—C4—C7—C8 | 50.19 (15) | C14—C19—C20—N2 | 176.62 (12) |
C3—C4—C7—C21 | 103.05 (14) | C18—C19—C20—C21 | −175.49 (13) |
C5—C4—C7—C21 | −75.66 (14) | C14—C19—C20—C21 | 0.40 (14) |
C3—C4—C7—C14 | −6.91 (17) | C22—N1—C21—C20 | −1.39 (17) |
C5—C4—C7—C14 | 174.37 (11) | C22—N1—C21—C7 | 178.39 (11) |
C21—C7—C8—C13 | −13.19 (16) | N2—C20—C21—N1 | −0.19 (19) |
C4—C7—C8—C13 | −135.71 (13) | C19—C20—C21—N1 | 176.19 (11) |
C14—C7—C8—C13 | 98.41 (14) | N2—C20—C21—C7 | 180.00 (11) |
C21—C7—C8—C9 | 169.96 (11) | C19—C20—C21—C7 | −3.62 (13) |
C4—C7—C8—C9 | 47.44 (15) | C8—C7—C21—N1 | −57.34 (16) |
C14—C7—C8—C9 | −78.44 (14) | C4—C7—C21—N1 | 66.59 (15) |
C13—C8—C9—C10 | −1.1 (2) | C14—C7—C21—N1 | −174.85 (12) |
C7—C8—C9—C10 | 175.84 (12) | C8—C7—C21—C20 | 122.46 (11) |
C8—C9—C10—C11 | 1.4 (2) | C4—C7—C21—C20 | −113.61 (11) |
C9—C10—C11—C12 | −0.1 (3) | C14—C7—C21—C20 | 4.95 (12) |
C10—C11—C12—C13 | −1.5 (3) | C21—N1—C22—C27 | −177.33 (11) |
C9—C8—C13—C12 | −0.4 (2) | C21—N1—C22—C23 | 1.35 (17) |
C7—C8—C13—C12 | −177.30 (13) | C20—N2—C23—C24 | 176.38 (11) |
C11—C12—C13—C8 | 1.8 (2) | C20—N2—C23—C22 | −1.72 (17) |
C8—C7—C14—C15 | 52.10 (17) | N1—C22—C23—N2 | 0.21 (19) |
C21—C7—C14—C15 | 172.54 (13) | C27—C22—C23—N2 | 178.89 (11) |
C4—C7—C14—C15 | −72.51 (17) | N1—C22—C23—C24 | −177.89 (11) |
C8—C7—C14—C19 | −125.24 (12) | C27—C22—C23—C24 | 0.79 (18) |
C21—C7—C14—C19 | −4.80 (13) | N2—C23—C24—C25 | −179.05 (13) |
C4—C7—C14—C19 | 110.15 (12) | C22—C23—C24—C25 | −0.9 (2) |
C19—C14—C15—C16 | −0.8 (2) | C23—C24—C25—C26 | 0.6 (2) |
C7—C14—C15—C16 | −177.99 (13) | C24—C25—C26—C27 | −0.2 (2) |
C14—C15—C16—C17 | −0.4 (2) | C25—C26—C27—C22 | 0.1 (2) |
C15—C16—C17—C18 | 0.7 (2) | N1—C22—C27—C26 | 178.29 (12) |
C16—C17—C18—C19 | 0.1 (2) | C23—C22—C27—C26 | −0.4 (2) |
Cg2 and Cg3 are the centroids of the N1/N2/C20–C23 and C1–C6 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···Cg2i | 0.93 | 2.92 | 3.728 (2) | 145 |
C25—H25···Cg3ii | 0.93 | 2.96 | 3.830 (3) | 156 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+1, −y+1, −z+1. |
Acknowledgements
The authors thank the Center of Testing and Analysis, Nanjing University, for support.
Funding information
Funding for this research was provided by: Natural Science Foundation of Jiangsu Province (grant No. BK20181486); Natural Science Foundation of the Jiangsu Higher Education Institutions (grant No. 17KJB320001); Overseas Training Program for Excellent Young Teachers and Principals of Jiangsu Province; Qing Lan Project of Jiangsu Province.
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