Home The crystal structure of 5-(2-chloro-3-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)-10,11-dihydro-5H-dibenzo[b,f]azepine, C40H39ClN2
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The crystal structure of 5-(2-chloro-3-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)-10,11-dihydro-5H-dibenzo[b,f]azepine, C40H39ClN2

  • Bangjin Sun ORCID logo and Zhenlong Tu EMAIL logo
Published/Copyright: January 4, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 2

Abstract

C40H39ClN2, monoclinic, P21/c (no. 14), a = 14.6448(2) Å, b = 11.1193(2) Å, c = 19.9769(4) Å, β = 98.741(2)°, V = 3215.25(10) Å3, Z = 4, R gt (F) = 0.0559, wR ref (F2) = 0.1614, T = 200 K.

CCDC no.: 2322339

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colorless block
Size: 0.14 × 0.12 × 0.10 mm
Wavelength: Cu Kα radiation (1.54184 Å)
μ: 1.27 mm−1
Diffractometer, scan mode: SuperNova, ω
θmax, completeness: 73.9°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 11,626, 6310, 0.029
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 5580
N(param)refined: 426
Programs: Bruker [1], Olex2 [2], SHELX [3, 4]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z Uiso*/Ueq
Cl1 0.54567 (3) 0.51380 (4) 0.24869 (2) 0.03895 (16)
N1 0.41817 (10) 0.66357 (14) 0.31238 (7) 0.0321 (3)
N2 0.71972 (9) 0.65802 (13) 0.23684 (7) 0.0308 (3)
C1 0.36299 (12) 0.69864 (16) 0.18826 (9) 0.0339 (4)
H1 0.417969 0.736323 0.179073 0.041*
C2 0.28796 (13) 0.68290 (16) 0.13779 (9) 0.0345 (4)
H2 0.292739 0.709714 0.093305 0.041*
C4 0.19892 (11) 0.58973 (14) 0.21479 (8) 0.0287 (3)
H4 0.143290 0.553981 0.224107 0.034*
C5 0.27346 (11) 0.60222 (14) 0.26673 (8) 0.0263 (3)
C6 0.35508 (11) 0.65740 (15) 0.25286 (8) 0.0289 (3)
C7 0.37847 (11) 0.61100 (15) 0.36442 (8) 0.0298 (3)
C8 0.28884 (11) 0.57138 (14) 0.33789 (8) 0.0278 (3)
C9 0.23575 (11) 0.51276 (15) 0.38053 (9) 0.0296 (3)
H9 0.175607 0.484816 0.362844 0.036*
C10 0.27014 (12) 0.49506 (16) 0.44844 (9) 0.0334 (4)
C11 0.35937 (13) 0.53693 (19) 0.47297 (9) 0.0398 (4)
H11 0.383130 0.525438 0.519480 0.048*
C12 0.41438 (12) 0.59455 (19) 0.43190 (9) 0.0380 (4)
H12 0.474710 0.621751 0.449639 0.046*
C13 0.11194 (18) 0.4649 (3) 0.48081 (16) 0.0718 (8)
H13A 0.107283 0.552357 0.485472 0.108*
H13B 0.077981 0.425306 0.513282 0.108*
H13C 0.085474 0.441184 0.434682 0.108*
C14 0.21268 (13) 0.42767 (18) 0.49471 (10) 0.0407 (4)
C15 0.2470 (2) 0.4508 (4) 0.56940 (14) 0.0895 (12)
H15A 0.309853 0.419164 0.581195 0.134*
H15B 0.206096 0.410544 0.596886 0.134*
H15C 0.247145 0.537481 0.578203 0.134*
C16 0.2166 (3) 0.2946 (3) 0.4805 (2) 0.1170 (18)
H16A 0.191841 0.279325 0.432914 0.176*
H16B 0.179620 0.251051 0.509600 0.176*
H16C 0.280825 0.267066 0.489879 0.176*
C17 0.50901 (11) 0.71064 (15) 0.31729 (8) 0.0296 (3)
C18 0.57320 (11) 0.65461 (14) 0.28213 (8) 0.0289 (3)
C19 0.65897 (11) 0.70869 (14) 0.27746 (8) 0.0276 (3)
C20 0.68143 (12) 0.81137 (15) 0.31678 (9) 0.0327 (4)
H20 0.739584 0.848878 0.316175 0.039*
C21 0.62132 (13) 0.85988 (16) 0.35656 (10) 0.0370 (4)
H21 0.640314 0.926830 0.384816 0.044*
C22 0.53391 (12) 0.81235 (16) 0.35582 (9) 0.0337 (4)
H22 0.491655 0.848830 0.381304 0.040*
C23 0.68598 (12) 0.61361 (18) 0.17078 (9) 0.0373 (4)
C24 0.62169 (15) 0.6831 (2) 0.12907 (11) 0.0524 (5)
H24 0.603044 0.758663 0.144665 0.063*
C25 0.58487 (18) 0.6431 (4) 0.06523 (13) 0.0728 (9)
H25 0.539998 0.690356 0.037572 0.087*
C26 0.6128 (2) 0.5354 (4) 0.04153 (12) 0.0771 (10)
H26 0.588103 0.508132 −0.002587 0.092*
C27 0.67693 (19) 0.4675 (3) 0.08243 (12) 0.0636 (7)
H27 0.696465 0.393466 0.065495 0.076*
C28 0.71457 (15) 0.50280 (19) 0.14789 (10) 0.0440 (5)
C29 0.78103 (16) 0.41633 (19) 0.18861 (12) 0.0516 (5)
H29A 0.838643 0.415443 0.168328 0.062*
H29B 0.753900 0.334754 0.182750 0.062*
C30 0.80738 (15) 0.43880 (17) 0.26422 (11) 0.0440 (5)
H30A 0.750751 0.444373 0.285529 0.053*
H30B 0.844691 0.370570 0.285185 0.053*
C31 0.86163 (12) 0.55285 (16) 0.27657 (9) 0.0339 (4)
C32 0.81757 (11) 0.66091 (15) 0.25797 (8) 0.0296 (3)
C33 0.86779 (13) 0.76698 (17) 0.25890 (10) 0.0382 (4)
H33 0.838047 0.839355 0.242391 0.046*
C34 0.96131 (13) 0.76710 (19) 0.28394 (12) 0.0471 (5)
H34 0.995508 0.839897 0.285355 0.057*
C35 1.00482 (14) 0.6617 (2) 0.30682 (12) 0.0507 (5)
H35 1.068294 0.662479 0.325975 0.061*
C36 0.95596 (14) 0.5550 (2) 0.30183 (11) 0.0457 (5)
H36 0.986931 0.482062 0.315772 0.055*
C37a 0.1142 (5) 0.7135 (7) 0.0429 (4) 0.082 (3)
H37Aa 0.110043 0.789292 0.067234 0.123*
H37Ba 0.058093 0.702493 0.009809 0.123*
H37Ca 0.168136 0.715505 0.019310 0.123*
C38a 0.1382 (5) 0.4962 (8) 0.0570 (5) 0.081 (3)
H38Aa 0.195809 0.500626 0.037775 0.122*
H38Ba 0.086366 0.482339 0.020538 0.122*
H38Ca 0.141884 0.429746 0.089511 0.122*
C39a 0.0299 (3) 0.6000 (9) 0.1198 (2) 0.071 (2)
H39Aa 0.027819 0.522792 0.143170 0.106*
H39Ba −0.021288 0.604371 0.082115 0.106*
H39Ca 0.024384 0.665760 0.151661 0.106*
C40 0.12356 (13) 0.61151 (17) 0.09204 (9) 0.0375 (4)
C41 0.20497 (12) 0.62892 (15) 0.14954 (9) 0.0311 (4)
C42b 0.1519 (5) 0.6395 (11) 0.0210 (3) 0.081 (3)
H42Ab 0.170857 0.723834 0.019485 0.121*
H42Bb 0.099048 0.624827 −0.014465 0.121*
H42Cb 0.203330 0.587310 0.013649 0.121*
C43b 0.0479 (5) 0.6925 (11) 0.1026 (4) 0.085 (4)
H43Ab 0.031935 0.679532 0.147906 0.128*
H43Bb −0.006204 0.675872 0.068493 0.128*
H43Cb 0.067346 0.776088 0.098272 0.128*
C44b 0.0972 (9) 0.4822 (7) 0.0881 (6) 0.097 (5)
H44Ab 0.149470 0.434159 0.077785 0.146*
H44Bb 0.044250 0.470800 0.052311 0.146*
H44Cb 0.080640 0.456340 0.131581 0.146*

  1. aOccupancy: 0.546 (10), bOccupancy: 0.454 (10).

1 Source of materials

The synthesis consists of two steps. In the first step, a mixture of 1-bromo-2-chloro-3-fluorobenzene (418 mg, 2 mmol), 3,6-di-tert-butyl-9H-carbazole (558 mg, 2 mmol) and cesium carbonate (976 mg, 3 mmol) in 50 mL dry DMF under nitrogen was stirred at 130 °C for 12 h. After cooling down to room temperature, the solvent was evaporated to give intermediate 9-(3-bromo-2-chlorophenyl)-3,6-di-tert-butyl-9H-carbazole. The crude intermediate was purified by column chromatography (silica gel, ethyl acetate/hexane) to afford a white solid. In the second step, 9-(3-bromo-2-chlorophenyl)-3,6-di-tert-butyl-9H-carbazole (469 mg, 1 mmol), 10,11-dihydro-5H-dibenzo[b,f]azepine (234 mg, 1.2 mmol) and sodium tert-butoxide were dissolved in 50 mL toluene under nitrogen atmosphere. The reaction mixture was stirred for 15 min before adding Pd2(dba)3 (46 mg, 0.05 mmol) and BF4HP(t–Bu)3 (58 mg, 0.2 mmol). The reaction mixture was stirred at reflux for 24 h. The resulting mixture was cooled to room temperature and then poured into a large amount of water for extraction with toluene. The combined organic phase was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane/petroleum as eluent to afford a white solid. Crystals of the title compound were obtained by slow evaporation.

2 Experimental details

Using Olex2 [2], the structure was solved with the ShelXS [3] structure solution program and refined with the ShelXL [4] refinement package.

3 Comment

The demand for ultra-high definition (UHD) displays has been steadily increasing, leading to the development of high-resolution standards in display technology. To achieve this standard, light sources require a narrow full width at half-maximum (FWHM) [5]. Thermally activated delayed fluorescence (TADF) molecules based on multiple resonance (MR) effects exhibit a rigid framework with regular arrangements of boron and nitrogen atoms, which allows to separate highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) at the atomic scale [6]. Consequently, MR–TADF materials exhibit reduced vibrational motion and narrow FWHM.

The boron containing compounds are mainly synthesized via a tandem lithiation-borylation-annulation reaction using aryl halides. Herein, an intermediate with carbazole (Cz) and azepine (Az) is synthesized. In the molecular structure, The C–N bond lengths of the Cz rings were 1.392(2) Å and 1.394(2) Å, while the one that connects the Cz rings were slightly longer, at 1.419(2) Å. Compared to pentacyclic carbazole, the C–N bond length of Az is slightly longer, which is 1.425(2) Å (N2–C23) and 1.431(2) Å (N2–C32), respectively [7, 8]. The angles of C23–N2–C32 and C6–N1–C7 were measured at 118.14(14)° and 108.56(13)°, respectively. Cz is almost coplanar with the dihedral angle of 177.96(14)° (C4–C5–C6–N1) and 178.55(14)° (N1–C7–C8–C9). The groups C23–N2–C32–C31 exhibit torsion angles with the value of −76.0(2)°, which indicate that the heptatomic ring in the Az fragment has an obvious fold. All the bond lengths and angles of this molecule are in the expected ranges.

Corresponding author: Zhenlong Tu, Shenzhen Institute of Information Technology, 518172 Longxiang Avenue No. 2188, Longgang District, Shenzhen, P.R. China, E-mail:

  1. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

  2. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  3. Research funding: The China Postdoctoral Science Foundation (2022M710020), The Science and Technology Project of Shenzhen City (JSGG20210802154213040).

References

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Received: 2023-11-08
Accepted: 2023-12-28
Published Online: 2024-01-04
Published in Print: 2024-04-25

© 2023 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  51. Crystal structure of catena-poly[triaqua-(μ2 -1-(4-carboxylatophenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ3O,O′:O′′)manganese(II)], C12H12N2O8Mn
  52. The crystal structure of [hexaaquamagnesium(II)] 4-[(pyridine-4-carbonyl)-amino]-phthalate trihydrate, C14H26N2O14Mg
  53. Crystal structure of 1-(p-tolylphenyl)-4-(2-furoyl)-3-methyl-1H-pyrazol-5-ol, C16H14N2O3
  54. The crystal structure of bis(1,4,7,10,13-pentaoxacyclopentadecane)-potassium(I) dichloridocopper(I), C20H40Cl2CuKO10
  55. The crystal structure of tris(tetra-n-butylammonium) hexanitrato-κ2O,O′-lanthanium(III) C48H108N9O18La
https://doi.org/10.1515/ncrs-2023-0488
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Solvothermal synthesis and crystal structure of aqua-tris(p-acetamidobenzoate-κ2O,O′)-(2,2′-bipyridine-κ2N,N′)terbium(III) - water - methanol (1/1/1)
  4. Crystal structure of hexaaquazinc(II) catena-poly[bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ2O,O′)-bis(μ2-1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ2O:O′)trizinc(II)] hexahydrate C26H36N4O20Zn2
  5. The crystal structure of valinyl-N-ium-4-(5-(thiophen-2-yl)isoxazol-3-yl)phenyl trifluoroacetate
  6. Crystal structure of bis(3,5-diisopropyl-1H-pyrazol-4-ammonium) tetrafluoroterephthalate, 2[C9H18N3][C8F4O4]
  7. Crystal structure of aqua-octakis(μ3-salicylato)-(1,10-phenanthroline)-(acetonitrile)-dicobalt(II)-trititanium(IV), C70H45N3O25Co2Ti3
  8. Crystal structure of catena-poly[aqua-(μ2-4,4′-diimidazole diphenyl ether-κ2N:N′)-(sulfato-κ1O)-cobalt(II)] – dimethylformamide (2/1), C39H37CoN9O8S
  9. Crystal structure of (5R,8R,9R,10R,12R, 13R,14R,17S)-2-(E-3-fluorobenzylidene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl) hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C37H53FO3
  10. Crystal structure of (Z)-4-((4,5,6-trimethoxy-3-oxobenzofuran-2(3H)-ylidene)methyl)phenyl diphenylphosphinate, C30H25O7P
  11. Crystal structure of 3-((5-methylpyridin-2-yl)amino)-1-phenylpropan-1-one, C15H16N2O
  12. The crystal structure of (R)-9-(5-methoxy-2-methyl-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-ylidene)-9H-thioxanthene, C28H22OS
  13. Crystal structure of diaqua-bis[1-(1-(hydroxymethyl)-1H-pyrazol-3-yl)-5-methyl-1H-1,2,3-triazole-4-carboxylato-κ2N,O)] manganese(II), C16H20MnN10O8
  14. The crystal structure of t-butyl 7-[4-(4-fluorophenyl)-2-[(methanesulfonyl)(methyl)amino]-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate, C26H36FN3O6S
  15. The crystal structure of samarium sulfate pentahydrate, Sm2(SO4)3(H2O)5
  16. The crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ 4 N,O,O,O)-zinc(II)] monohydrate, C12H15NO9Zn
  17. The crystal structure of 2,3-difluoro-11H-benzo-[4,5]imidazo[2,1-a]isoindol-11-one, C14H6F2N2O
  18. The crystal structure of 2,3-di(9H-carbazol-9-yl)-9H-fluoren-9-one, C37H22N2O
  19. The crystal structure of 5-(2-chloro-3-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)-10,11-dihydro-5H-dibenzo[b,f]azepine, C40H39ClN2
  20. Crystal structure of 2-bromo-1-hydroxy-3-(3-methylbut-2-enyloxy)-9H-xanthen-9-one, C18H15BrO4
  21. Crystal structure of bis(μ2-benzenesulfonato-κ2O:O′)-bis(μ2-6,6′-((ethane-1,2-diylbis(azaneylylidene))bis(methaneylylidene))-bis(2-methoxyphenolato-κ6O,O′:O′,N,N′,O′′:O′′,O′′′))disodium(I)dicopper(II)
  22. The crystal structure of (E)-1,2-bis(benzo[e][1,2]azaborinin-2(1H)-yl)ethene, C18H16B2N2
  23. Crystal structure of 3-oxo-urs-12-en-28-benzyl ester, C37H52O3
  24. The crystal structure of ethyl (E)-1-chloro-3-(4-chloro-1-methyl-1H-indole-2-carbonyl)-4-oxo-2-phenylcyclooct-2-ene-1-carboxylate, C27H25Cl2NO4
  25. The crystal structure of 4,4′-((5-bromo-2-iodo-1,3-phenylene)bis(oxy))bis(tert-butylbenzene) ─ ethanol (2/1), C26H28BrIO2
  26. Crystal structure of (E)-1-(4-(benzyloxy)-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one, C18H19NO3
  27. The crystal structure of N1,N3-bis(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)\ propanediamide hydrate, C25H26N6O4, 2(H2O)
  28. The crystal structure of 2,5-bis[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)amino]cyclohexa-2,5-diene-1,4-dione, C28H26N6O4
  29. Crystal structure of 3,4-bis[2-(hydroxymethyl)-pyrrolidin-1-yl] cyclobut-3-ene-1,2-dione hydrate, C14H22N2O5
  30. The crystal structure of 2-(3,4–dichlorobenzyl)-1H-benzimidazole, C14H10Cl2N2
  31. The crystal structure of 2-(2-((4,6-dimethoxypyrimidin-2-yl)oxy)phenyl)-4-(piperidin-1-yl)-5H-chromeno[2,3-d]pyrimidine, C28H27N5O4
  32. The crystal structure of 6-(benzofuran-2-yl)-2-oxo-4,5-diphenyl-3,4-dihydro-2H-pyran-3-carbonitrile, C26H17NO3
  33. Crystal structure of N-(4-bromobenzyl)-3-(difluoromethyl)-1-methyl-N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide, C18H15BrF2N4O
  34. The crystal structure of the host-guest complex: N′-{5-[2-(2,6-dimethylphenoxy)acetamido]-4-hydroxy-1,6-diphenylhexan-2-yl}-3-methyl-2-(2-oxo-1,3-diazinan-1-yl)butanamide-diethyl ether (2/1)
  35. The crystal structure of (Z)-4-amino-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H17N3O2
  36. The crystal structure of diethyl 1,4-dihydro-2,6-dimethyl-4-(3-cyanophenyl)-3,5-pyridinedicarboxylate, C20H22N2O4
  37. Crystal structure of 3-(5-((4-(difluoromethoxy)phenyl) sulfonyl)-3,4,5,6-tetrahydropyrrolo[3,4-c]pyrrol-2(1H)-yl) oxetane-3-carboxamide, C17H19F2N3O5S
  38. Crystal structure of 2-((2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)amino)-N-(2-(4-methylpiperazin-1-yl)ethyl)benzamide hydrate, C25H37Cl2N5O6
  39. Crystal structure of 3-(benzo[d]thiazol-2-yl)-5-bromo-2-hydroxybenzaldehyde, C14H8BrNO2S
  40. Crystal structure of 3-(difluoromethyl)-1-methyl-N-(pyridin-2-yl)-1H-pyrazole-4-carboxamide, C11H10F2N4O
  41. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-isopropyl-1H-imidazol-3-ium hexafluoridophosphate(V), C20H34F12N4P2
  42. Crystal structure of ethyl 5,6-dichloro-2-methyl-2,3-dihydro-1 H-benzo[d]imidazole-2-carboxylate, C11H12Cl2N2O2
  43. The crystal of structure of (OC-6-22)-pentakis(acetonitrile)bromidoruthenium(II)bromide monohydrate, C10H15Br2N5Ru
  44. Crystal structure of (2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(((4aS,5R,6S)-1-oxo-5-vinyl-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl)oxy)tetrahydro-2H-pyran-3-yl 2,3-dihydroxybenzoate hydrate, C23H26O12·H2O
  45. The crystal structure of (E)-4-amino-N′-(1-(4-fluorophenyl)propylidene)benzohydrazide, C16H16FN3O
  46. The crystal structure of 2′-(9H-carbazol-9-yl)-[1,1′-binaphthalen]-2-amine, C32H22N2
  47. Crystal structure of poly[μ3-diiodido-[μ2-di(1H-pyrazol-1-yl)methane-κ2N,N′)]dicopper(I)], C7H8Cu2I2N4
  48. Crystal structure of 3-amino-N′-hydroxy-1H-pyrazole-4-carboximidamide, C4H7N5O
  49. The crystal structure of 1,3-diacetyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, C8H10O4N4
  50. Crystal structure of catena-poly[aqua-(μ2-1,4-diazabicyclo[2.2.2]octane-k2N: N′)-bis(sorbato-κ1O)-copper(II), C18H28CuN2O5
  51. Crystal structure of catena-poly[triaqua-(μ2 -1-(4-carboxylatophenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylato-κ3O,O′:O′′)manganese(II)], C12H12N2O8Mn
  52. The crystal structure of [hexaaquamagnesium(II)] 4-[(pyridine-4-carbonyl)-amino]-phthalate trihydrate, C14H26N2O14Mg
  53. Crystal structure of 1-(p-tolylphenyl)-4-(2-furoyl)-3-methyl-1H-pyrazol-5-ol, C16H14N2O3
  54. The crystal structure of bis(1,4,7,10,13-pentaoxacyclopentadecane)-potassium(I) dichloridocopper(I), C20H40Cl2CuKO10
  55. The crystal structure of tris(tetra-n-butylammonium) hexanitrato-κ2O,O′-lanthanium(III) C48H108N9O18La
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