organic compounds
7,8-Dimethyl-11H-indeno[1,2-b]quinoxalin-11-one
aTargeted MRI Contrast Agents Laboratory of Jiangsu Province, Nanjing Polytechnic Institute, Nanjing 210048, People's Republic of China, and bSchool of Biology and Environment, Nanjing Polytechnic Institute, Nanjing 210048, People's Republic of China
*Correspondence e-mail: njutshs@126.com
In the title compound, C17H12N2O, the mean planes of the indene ring and quinoxaline system (r.m.s. deviations = 0.0131 and 0.0082 Å) are approximately parallel to one another, making a dihedral angle of 1.2 (5)°. This means that the indeno[1,2-b]quinoxaline ring is almost in the same plane (r.m.s. deviation = 0.0181 Å).
Keywords: crystal structure; indene; quinoxaline; indeno[1,2-b]quinoxaline.
CCDC reference: 2054191
Structure description
Quinoxaline based N-heteroacenes show a narrow band-gap, high thermal stability and aligned film morphology and 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 indene ring and quinoxaline system are nearly parallel to one another [dihedral angle = 1.2 (5)°]. This means that the indeno[1,2-b]quinoxaline ring (N1–N2/C1–C15) is almost in the same plane (r.m.s. deviation = 0.0181 Å), which contains the two methyl groups. The packing is shown in Fig. 2.
One similar structure has been reported previously (11,11-diphenyl-11H-indeno[1,2-b]quinoxaline; Chen et al., 2020). In that structure, the indeno[1,2-b]quinoxaline ring (r.m.s. deviations = 0.1197 Å) is twisted with respect to the two benzene ring systems by 70.0 (4) and 67.6 (3)°, respectively.
Synthesis and crystallization
A mixture of 1H-indene-1,2,3-trione (3.20 g, 20 mmol) and 4,5-dimethylbenzene-1,2-diamine (2.72 g, 20 mmol) in ethanol (100 ml) was heated to reflux under stirring for 5 h. 7,8-Dimethyl-11H-indeno[1,2-b]quinoxalin-11-one was obtained as a yellow powder by filtering after cooling, yield 82%. Single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of a methanol solution.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 1Structural data
CCDC reference: 2054191
https://doi.org/10.1107/S2414314621000183/xu4042sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621000183/xu4042Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314621000183/xu4042Isup3.cml
Data collection: SMART (Bruker, 2014); cell
SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); 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).C17H12N2O | F(000) = 544 |
Mr = 260.29 | Dx = 1.349 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4548 (9) Å | Cell parameters from 5967 reflections |
b = 22.976 (3) Å | θ = 2.7–28.4° |
c = 8.3149 (10) Å | µ = 0.09 mm−1 |
β = 115.866 (3)° | T = 282 K |
V = 1281.5 (3) Å3 | Block, colorless |
Z = 4 | 0.45 × 0.3 × 0.22 mm |
Bruker SMART CCD 6000 area detector diffractometer | 3134 independent reflections |
Radiation source: sealed X-ray tube | 2437 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 5.6 pixels mm-1 | θmax = 28.4°, θmin = 3.1° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | k = −30→30 |
Tmin = 0.606, Tmax = 0.746 | l = −11→5 |
10114 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.060 | H-atom parameters constrained |
wR(F2) = 0.153 | w = 1/[σ2(Fo2) + (0.0487P)2 + 0.7679P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3134 reflections | Δρmax = 0.27 e Å−3 |
183 parameters | Δρmin = −0.22 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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1899 (2) | 0.67104 (6) | 0.38760 (19) | 0.0613 (4) | |
N1 | 0.1135 (2) | 0.54175 (6) | 0.3195 (2) | 0.0400 (4) | |
N2 | 0.3665 (2) | 0.48258 (6) | 0.6458 (2) | 0.0417 (4) | |
C1 | 0.3614 (2) | 0.53906 (7) | 0.6270 (2) | 0.0348 (4) | |
C2 | 0.4780 (2) | 0.58312 (7) | 0.7599 (2) | 0.0366 (4) | |
C3 | 0.6183 (3) | 0.57743 (9) | 0.9349 (3) | 0.0483 (5) | |
H3 | 0.6505 | 0.5411 | 0.9892 | 0.058* | |
C4 | 0.7104 (3) | 0.62748 (10) | 1.0279 (3) | 0.0542 (5) | |
H4 | 0.8068 | 0.6244 | 1.1455 | 0.065* | |
C5 | 0.6616 (3) | 0.68157 (9) | 0.9493 (3) | 0.0517 (5) | |
H5 | 0.7257 | 0.7144 | 1.0146 | 0.062* | |
C6 | 0.5187 (3) | 0.68793 (8) | 0.7744 (3) | 0.0463 (5) | |
H6 | 0.4851 | 0.7245 | 0.7217 | 0.056* | |
C7 | 0.4275 (3) | 0.63822 (8) | 0.6807 (2) | 0.0381 (4) | |
C8 | 0.2716 (3) | 0.63268 (7) | 0.4928 (2) | 0.0400 (4) | |
C9 | 0.2358 (2) | 0.56799 (7) | 0.4648 (2) | 0.0362 (4) | |
C10 | 0.1132 (3) | 0.48201 (7) | 0.3342 (2) | 0.0381 (4) | |
C11 | −0.0140 (3) | 0.44895 (8) | 0.1861 (3) | 0.0448 (4) | |
H11 | −0.0943 | 0.4680 | 0.0802 | 0.054* | |
C12 | −0.0229 (3) | 0.38935 (8) | 0.1933 (3) | 0.0490 (5) | |
C13 | 0.1007 (3) | 0.36040 (8) | 0.3545 (3) | 0.0528 (5) | |
C14 | 0.2283 (3) | 0.39190 (8) | 0.4996 (3) | 0.0500 (5) | |
H14 | 0.3106 | 0.3723 | 0.6037 | 0.060* | |
C15 | 0.2382 (3) | 0.45313 (7) | 0.4951 (2) | 0.0389 (4) | |
C16 | 0.0931 (4) | 0.29501 (9) | 0.3674 (4) | 0.0773 (8) | |
H16A | 0.1901 | 0.2825 | 0.4830 | 0.116* | |
H16B | 0.1219 | 0.2775 | 0.2765 | 0.116* | |
H16C | −0.0375 | 0.2834 | 0.3511 | 0.116* | |
C17 | −0.1623 (4) | 0.35635 (10) | 0.0302 (4) | 0.0665 (7) | |
H17A | −0.2286 | 0.3831 | −0.0665 | 0.100* | |
H17B | −0.2595 | 0.3362 | 0.0560 | 0.100* | |
H17C | −0.0878 | 0.3287 | −0.0030 | 0.100* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0802 (11) | 0.0335 (7) | 0.0499 (8) | 0.0066 (7) | 0.0095 (7) | 0.0056 (6) |
N1 | 0.0444 (8) | 0.0322 (7) | 0.0406 (8) | 0.0024 (6) | 0.0159 (7) | 0.0001 (6) |
N2 | 0.0491 (9) | 0.0341 (7) | 0.0459 (9) | 0.0071 (6) | 0.0245 (7) | 0.0067 (6) |
C1 | 0.0365 (8) | 0.0343 (8) | 0.0375 (9) | 0.0055 (6) | 0.0197 (7) | 0.0032 (7) |
C2 | 0.0345 (8) | 0.0395 (9) | 0.0381 (9) | 0.0041 (7) | 0.0179 (7) | −0.0004 (7) |
C3 | 0.0451 (10) | 0.0541 (11) | 0.0408 (10) | 0.0099 (8) | 0.0143 (8) | 0.0063 (8) |
C4 | 0.0406 (10) | 0.0733 (14) | 0.0405 (10) | 0.0042 (9) | 0.0102 (8) | −0.0085 (10) |
C5 | 0.0409 (10) | 0.0557 (12) | 0.0533 (12) | −0.0030 (8) | 0.0157 (9) | −0.0163 (9) |
C6 | 0.0435 (10) | 0.0409 (10) | 0.0517 (11) | 0.0003 (8) | 0.0182 (9) | −0.0077 (8) |
C7 | 0.0371 (9) | 0.0388 (9) | 0.0399 (9) | 0.0026 (7) | 0.0181 (8) | −0.0024 (7) |
C8 | 0.0463 (10) | 0.0313 (8) | 0.0395 (9) | 0.0029 (7) | 0.0161 (8) | −0.0019 (7) |
C9 | 0.0386 (8) | 0.0317 (8) | 0.0389 (9) | 0.0030 (6) | 0.0175 (7) | 0.0015 (7) |
C10 | 0.0419 (9) | 0.0337 (8) | 0.0457 (10) | −0.0001 (7) | 0.0257 (8) | −0.0023 (7) |
C11 | 0.0485 (10) | 0.0413 (10) | 0.0499 (11) | −0.0045 (8) | 0.0264 (9) | −0.0078 (8) |
C12 | 0.0565 (11) | 0.0417 (10) | 0.0663 (13) | −0.0115 (8) | 0.0429 (11) | −0.0148 (9) |
C13 | 0.0715 (13) | 0.0330 (9) | 0.0784 (15) | −0.0068 (9) | 0.0554 (12) | −0.0073 (9) |
C14 | 0.0690 (13) | 0.0325 (9) | 0.0617 (12) | 0.0054 (8) | 0.0408 (11) | 0.0060 (8) |
C15 | 0.0467 (9) | 0.0320 (8) | 0.0488 (10) | 0.0026 (7) | 0.0308 (8) | 0.0015 (7) |
C16 | 0.114 (2) | 0.0324 (10) | 0.112 (2) | −0.0109 (12) | 0.0750 (19) | −0.0078 (12) |
C17 | 0.0766 (15) | 0.0572 (13) | 0.0820 (17) | −0.0262 (11) | 0.0497 (14) | −0.0305 (12) |
O1—C8 | 1.203 (2) | C8—C9 | 1.510 (2) |
N1—C9 | 1.301 (2) | C10—C11 | 1.405 (2) |
N1—C10 | 1.378 (2) | C10—C15 | 1.418 (3) |
N2—C1 | 1.306 (2) | C11—H11 | 0.9300 |
N2—C15 | 1.377 (2) | C11—C12 | 1.374 (3) |
C1—C2 | 1.471 (2) | C12—C13 | 1.418 (3) |
C1—C9 | 1.427 (2) | C12—C17 | 1.505 (3) |
C2—C3 | 1.378 (3) | C13—C14 | 1.372 (3) |
C2—C7 | 1.401 (2) | C13—C16 | 1.509 (3) |
C3—H3 | 0.9300 | C14—H14 | 0.9300 |
C3—C4 | 1.389 (3) | C14—C15 | 1.410 (2) |
C4—H4 | 0.9300 | C16—H16A | 0.9600 |
C4—C5 | 1.377 (3) | C16—H16B | 0.9600 |
C5—H5 | 0.9300 | C16—H16C | 0.9600 |
C5—C6 | 1.385 (3) | C17—H17A | 0.9600 |
C6—H6 | 0.9300 | C17—H17B | 0.9600 |
C6—C7 | 1.382 (2) | C17—H17C | 0.9600 |
C7—C8 | 1.491 (2) | ||
C9—N1—C10 | 114.01 (15) | N1—C10—C15 | 121.59 (16) |
C1—N2—C15 | 114.02 (15) | C11—C10—C15 | 119.23 (16) |
N2—C1—C2 | 128.14 (16) | C10—C11—H11 | 119.1 |
N2—C1—C9 | 123.29 (16) | C12—C11—C10 | 121.88 (19) |
C9—C1—C2 | 108.57 (14) | C12—C11—H11 | 119.1 |
C3—C2—C1 | 130.93 (17) | C11—C12—C13 | 118.99 (18) |
C3—C2—C7 | 120.44 (17) | C11—C12—C17 | 119.4 (2) |
C7—C2—C1 | 108.62 (15) | C13—C12—C17 | 121.62 (19) |
C2—C3—H3 | 120.9 | C12—C13—C16 | 120.3 (2) |
C2—C3—C4 | 118.18 (19) | C14—C13—C12 | 119.94 (17) |
C4—C3—H3 | 120.9 | C14—C13—C16 | 119.7 (2) |
C3—C4—H4 | 119.4 | C13—C14—H14 | 119.1 |
C5—C4—C3 | 121.26 (19) | C13—C14—C15 | 121.82 (19) |
C5—C4—H4 | 119.4 | C15—C14—H14 | 119.1 |
C4—C5—H5 | 119.5 | N2—C15—C10 | 122.55 (15) |
C4—C5—C6 | 121.09 (19) | N2—C15—C14 | 119.32 (17) |
C6—C5—H5 | 119.5 | C14—C15—C10 | 118.13 (17) |
C5—C6—H6 | 121.0 | C13—C16—H16A | 109.5 |
C7—C6—C5 | 117.92 (18) | C13—C16—H16B | 109.5 |
C7—C6—H6 | 121.0 | C13—C16—H16C | 109.5 |
C2—C7—C8 | 110.02 (15) | H16A—C16—H16B | 109.5 |
C6—C7—C2 | 121.10 (17) | H16A—C16—H16C | 109.5 |
C6—C7—C8 | 128.89 (17) | H16B—C16—H16C | 109.5 |
O1—C8—C7 | 127.95 (16) | C12—C17—H17A | 109.5 |
O1—C8—C9 | 127.57 (17) | C12—C17—H17B | 109.5 |
C7—C8—C9 | 104.47 (14) | C12—C17—H17C | 109.5 |
N1—C9—C1 | 124.53 (15) | H17A—C17—H17B | 109.5 |
N1—C9—C8 | 127.17 (15) | H17A—C17—H17C | 109.5 |
C1—C9—C8 | 108.30 (14) | H17B—C17—H17C | 109.5 |
N1—C10—C11 | 119.18 (16) | ||
O1—C8—C9—N1 | 2.1 (3) | C6—C7—C8—C9 | 178.41 (18) |
O1—C8—C9—C1 | −178.2 (2) | C7—C2—C3—C4 | −1.4 (3) |
N1—C10—C11—C12 | −179.08 (17) | C7—C8—C9—N1 | −179.01 (17) |
N1—C10—C15—N2 | 0.1 (3) | C7—C8—C9—C1 | 0.66 (18) |
N1—C10—C15—C14 | 179.67 (16) | C9—N1—C10—C11 | 179.60 (16) |
N2—C1—C2—C3 | −0.6 (3) | C9—N1—C10—C15 | −0.4 (2) |
N2—C1—C2—C7 | 178.74 (17) | C9—C1—C2—C3 | 179.88 (18) |
N2—C1—C9—N1 | 0.2 (3) | C9—C1—C2—C7 | −0.79 (19) |
N2—C1—C9—C8 | −179.51 (16) | C10—N1—C9—C1 | 0.3 (2) |
C1—N2—C15—C10 | 0.3 (2) | C10—N1—C9—C8 | 179.93 (16) |
C1—N2—C15—C14 | −179.21 (16) | C10—C11—C12—C13 | −0.4 (3) |
C1—C2—C3—C4 | 177.84 (18) | C10—C11—C12—C17 | 179.93 (17) |
C1—C2—C7—C6 | −178.38 (16) | C11—C10—C15—N2 | −179.92 (16) |
C1—C2—C7—C8 | 1.22 (19) | C11—C10—C15—C14 | −0.4 (2) |
C2—C1—C9—N1 | 179.72 (16) | C11—C12—C13—C14 | −0.7 (3) |
C2—C1—C9—C8 | 0.04 (18) | C11—C12—C13—C16 | 179.44 (19) |
C2—C3—C4—C5 | 0.9 (3) | C12—C13—C14—C15 | 1.3 (3) |
C2—C7—C8—O1 | 177.7 (2) | C13—C14—C15—N2 | 178.80 (17) |
C2—C7—C8—C9 | −1.16 (19) | C13—C14—C15—C10 | −0.8 (3) |
C3—C2—C7—C6 | 1.0 (3) | C15—N2—C1—C2 | −179.95 (15) |
C3—C2—C7—C8 | −179.36 (16) | C15—N2—C1—C9 | −0.5 (2) |
C3—C4—C5—C6 | 0.0 (3) | C15—C10—C11—C12 | 1.0 (3) |
C4—C5—C6—C7 | −0.5 (3) | C16—C13—C14—C15 | −178.83 (19) |
C5—C6—C7—C2 | −0.1 (3) | C17—C12—C13—C14 | 178.92 (18) |
C5—C6—C7—C8 | −179.59 (18) | C17—C12—C13—C16 | −0.9 (3) |
C6—C7—C8—O1 | −2.7 (3) |
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); Training program of Students innovation and entrepreneurship in Jiangsu Province (grant No. 202012920001Y); Qing Lan Project of Jiangsu Province.
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