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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 11| November 2016| x161776
https://doi.org/10.1107/S2414314616017764

9-Butyl-3-nitro-9H-carbazole

CROSSMARK_Color_square_no_text.svg
Zhang Ping,a Zhang Tingb and Chang-Chun Songb*

aDeparment of Chemistry, Anhui Science and Technology University, Fengyang 233100, People's Republic of China, and bDepartment of Chemistry, Anhui Science and Technology University, Fengyang 233100, People's Republic of China
*Correspondence e-mail: songcc@ahstu.edu.cn

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 7 September 2016; accepted 7 November 2016; online 15 November 2016)

The title compound, C16H16N2O2, is a carbazole derivative with the 3-position substituted by a nitro group and the 9-position substituted by an n-butyl group. The nitro group is inclined to the benzene ring to which it is attached by 4.4 (2)°. The n-butyl substituent has an extended conformation and lies almost normal to the plane of the carbozole ring. In the crystal, inversion-related mol­ecules stack along the a axis and are linked via offset π–π inter­actions, forming columns [shortest inter­centroid distance = 3.773 (1) Å].

CCDC reference: 1515348

Similar articles
3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Carbazole-based materials are well known for their excellent thermal stability, hole-transporting properties, versatile structural derivatization, and their ability to form amorphous films. Such compounds have also been used to produce high-performance blue phospho­rescent organic light-emitting diodes (Ye et al., 2010[Ye, S. H., Liu, Y. Q., Chen, J. M., Lu, K., Wu, W. P., Du, C. Y., Liu, Y., Wu, T., Shuai, Z. G. & Yu, G. (2010). Adv. Mater. 22, 4167-4171.]). When a n-butyl group is introduced into the mol­ecule, it enhances the solubility and film-forming ability. A nitro group can form non-covalent inter­actions, especially hydrogen bonds, and exhibits a diversity of chemical and biological actions (Trzesowska-Kruszynska, 2015[Trzesowska-Kruszynska, A. T. (2015). CrystEngComm, 17, 7702-7716.]). The synthesis and crystal structure of the title compound, with both a butyl and a nitro substituent, is described herein.

In the title compound, Fig. 1[link], the bond lengths and angles are similar to those in the related compound 1-nitro-9H-carbazole (Kautny & Stöger, 2014[Kautny, P. & Stöger, B. (2014). Acta Cryst. E70, o28.]). The carbazole ring system is, as expected, almost planar (r.m.s. deviation = 0.01 Å) and the nitro group is inclined by 4.4 (2)° to the benzene ring to which it is attached. The n-butyl substituent has an extended conformation and lies almost normal to the plane of the carbozole ring system. Its mean plane is inclined to the central five-membered ring by 77.6 (2) °.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

In the crystal, inversion-related mol­ecules stack along the a axis and are linked via offset π–π inter­actions, forming columns (Fig. 2[link]). The shortest inter­centroid distance is Cg1⋯Cg3i = 3.773 (1) Å [Cg1 and Cg3 are the centroids of rings N2/C3/C6/C11/C16 and C11–C16, respectively, inter­planar distance = 3.536 (1) Å, slippage = 1.316 Å, symmetry code: (i) −x + 1, −y, −z + 2].

[Figure 2]
Figure 2
Crystal packing of the title compound, viewed along the a axis. H atoms have been omitted for clarity.

Synthesis and crystallization

The precursor N-(n-but­yl)-carbazole was prepared in accord with the literature method (Yang et al., 2005[Yang, J.-X., Tao, X.-T., Yuan, C. X., Yan, Y. X., Wang, L., Liu, Z., Ren, Y. & Jiang, M. H. (2005). J. Am. Chem. Soc. 127, 3278-3279.]). Carbazole (3.3 g, 20 mmol) was added to a mixture of NaOH (1.3 g, 32 mmol), Bu4NBr (0.3 g) as phase-transfer catalyst in 20 ml CH3COCH3. The mixture was stirred for 1 h and then 1-bromo­butane was slowly added. After refluxing for 24 h, no carbazole was present (monitoring by TLC). The solvents were removed under reduced pressure, and 20 ml water was added to the flask and a white solid precipitated out. The white solid was filtered and washed several times with water, dried and recrystallized from ethanol solution giving white needle-shaped crystals (yield: 4.1 g, 90.1%).

The title compound was prepared in accord with the literature methods (Shufen et al., 1995[Shufen, Z., Danhong, Z. & Jinzong, Y. (1995). Dyes Pigments, 27, 287-296.]; Zhang et al., 2014[Zhang, P., Liu, J., Huang, J. Y. & Yang, J. X. (2014). Chin. J. Appl. Chem. 31, 1171-1176.]). N-(n-but­yl)-carbazole (5.6 g, 25 mmol) was dissolved in di­chloro­methane (50 ml) and the solution cooled (ice–water bath) to 273–275 K. Concentrated nitric acid (65–68%, 2.2 ml, 32 mmol) was added dropwise over one hour with vigorous stirring. Stirring was continued for a further hour at 283 K, after which time all of the N-(n-but­yl)-carbazole had reacted. The liquor was steam distilled to remove di­chloro­methane, then the mixture was cooled and filtered and the product obtained was washed several times with water. The residue was purified by flash chromatography on silica gel using di­chloro­ethane as eluent (yield: 5.8 g, 86.5%). Yellow block-like crystals of the title compound, suitable for X-ray diffraction analysis, were grown from ethanol solution by slow evaporation at room temperature in about one week.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link].

Table 1
Experimental details

Crystal data
Chemical formula C16H16N2O2
Mr 268.31
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 296
a, b, c (Å) 8.1948 (9), 9.5630 (11), 9.7528 (11)
α, β, γ (°) 68.106 (1), 73.141 (1), 85.379 (1)
V (Å3) 678.37 (13)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.09
Crystal size (mm) 0.18 × 0.17 × 0.16
 
Data collection
Diffractometer Bruker SMART CCD area detector
Absorption correction Multi-scan (SADABS; Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.984, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections 4867, 2372, 2080
Rint 0.014
(sin θ/λ)max (Å−1) 0.594
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.113, 1.09
No. of reflections 2372
No. of parameters 183
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.24, −0.15
Computer programs: SMART and SAINT (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

Structural data

CCDC reference: 1515348

Crystal structure: contains datablocks I, Global. DOI: https://doi.org/10.1107/S2414314616017764/su4073sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616017764/su4073Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616017764/su4073Isup3.cml

checkCIF report


Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

9-Butyl-3-nitro-9H-carbazole top
Crystal data top
C16H16N2O2Z = 2
Mr = 268.31F(000) = 284
Triclinic, P1Dx = 1.314 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1948 (9) ÅCell parameters from 3094 reflections
b = 9.5630 (11) Åθ = 2.3–26.8°
c = 9.7528 (11) ŵ = 0.09 mm−1
α = 68.106 (1)°T = 296 K
β = 73.141 (1)°Block, light yellow
γ = 85.379 (1)°0.18 × 0.17 × 0.16 mm
V = 678.37 (13) Å3
Data collection top
Bruker SMART CCD area detector
diffractometer		2372 independent reflections
Radiation source: fine-focus sealed tube2080 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
phi and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		h = −9→9
Tmin = 0.984, Tmax = 0.986k = −11→11
4867 measured reflectionsl = −11→10
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0524P)2 + 0.1519P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
2372 reflectionsΔρmax = 0.24 e Å−3
183 parametersΔρmin = −0.15 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.029 (5)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N20.37033 (15)0.13986 (14)0.84237 (13)0.0458 (3)
N1−0.13392 (18)0.18235 (19)1.34577 (17)0.0603 (4)
O2−0.18313 (17)0.30664 (17)1.34766 (18)0.0832 (5)
O1−0.19381 (19)0.06376 (19)1.45000 (16)0.0867 (5)
C110.37310 (18)−0.01575 (16)0.88088 (16)0.0432 (3)
C20.04843 (19)0.03728 (17)1.20382 (17)0.0455 (4)
H2−0.0023−0.05141.28210.055*
C30.17430 (17)0.03417 (16)1.07446 (16)0.0410 (3)
C60.24994 (18)0.17125 (16)0.95749 (16)0.0425 (3)
C10.00093 (19)0.17611 (18)1.21260 (17)0.0477 (4)
C160.25369 (17)−0.08540 (16)1.02448 (16)0.0413 (3)
C40.0748 (2)0.31103 (18)1.09844 (19)0.0520 (4)
H40.03930.40211.10940.062*
C120.4732 (2)−0.09885 (19)0.79835 (18)0.0528 (4)
H120.5521−0.05210.70350.063*
C70.4756 (2)0.24856 (19)0.69959 (17)0.0533 (4)
H7A0.59050.21190.67820.064*
H7B0.48140.34340.71300.064*
C50.2000 (2)0.31044 (17)0.96963 (18)0.0509 (4)
H50.25010.40010.89270.061*
C150.2343 (2)−0.24194 (17)1.08728 (18)0.0499 (4)
H150.1560−0.28991.18220.060*
C130.4502 (2)−0.2532 (2)0.8634 (2)0.0591 (4)
H130.5146−0.31160.81070.071*
C80.4070 (2)0.2762 (2)0.56171 (17)0.0561 (4)
H8A0.48750.34200.46950.067*
H8B0.40030.18090.54950.067*
C90.2347 (2)0.3454 (2)0.5750 (2)0.0598 (4)
H9A0.24260.44470.57830.072*
H9B0.15510.28390.67060.072*
C140.3336 (2)−0.32454 (19)1.0057 (2)0.0575 (4)
H140.3223−0.42921.04650.069*
C100.1674 (3)0.3591 (3)0.4412 (2)0.0808 (6)
H10A0.23810.43000.34780.121*
H10B0.05260.39350.45920.121*
H10C0.16880.26250.43210.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0465 (7)0.0483 (7)0.0367 (6)0.0007 (5)−0.0075 (5)−0.0123 (5)
N10.0487 (8)0.0790 (10)0.0608 (9)0.0037 (7)−0.0083 (7)−0.0396 (8)
O20.0679 (8)0.0907 (10)0.1034 (11)0.0107 (7)−0.0029 (7)−0.0669 (9)
O10.0833 (10)0.0943 (11)0.0613 (8)−0.0012 (8)0.0146 (7)−0.0306 (8)
C110.0415 (7)0.0503 (8)0.0391 (7)0.0050 (6)−0.0145 (6)−0.0160 (6)
C20.0446 (8)0.0507 (9)0.0396 (7)−0.0024 (6)−0.0092 (6)−0.0159 (6)
C30.0411 (7)0.0457 (8)0.0377 (7)0.0008 (6)−0.0132 (6)−0.0152 (6)
C60.0431 (8)0.0474 (8)0.0383 (7)0.0014 (6)−0.0134 (6)−0.0155 (6)
C10.0438 (8)0.0598 (9)0.0460 (8)0.0043 (7)−0.0116 (6)−0.0280 (7)
C160.0406 (7)0.0474 (8)0.0387 (7)0.0025 (6)−0.0137 (6)−0.0171 (6)
C40.0559 (9)0.0503 (9)0.0575 (9)0.0081 (7)−0.0192 (7)−0.0272 (8)
C120.0477 (8)0.0665 (11)0.0442 (8)0.0101 (7)−0.0112 (7)−0.0231 (8)
C70.0451 (8)0.0620 (10)0.0426 (8)−0.0063 (7)−0.0068 (7)−0.0103 (7)
C50.0570 (9)0.0448 (8)0.0482 (8)−0.0009 (7)−0.0150 (7)−0.0134 (7)
C150.0512 (9)0.0485 (9)0.0486 (8)0.0001 (7)−0.0135 (7)−0.0163 (7)
C130.0601 (10)0.0648 (11)0.0615 (10)0.0185 (8)−0.0199 (8)−0.0347 (9)
C80.0540 (9)0.0622 (10)0.0401 (8)0.0013 (7)−0.0052 (7)−0.0114 (7)
C90.0602 (10)0.0641 (11)0.0574 (10)0.0065 (8)−0.0157 (8)−0.0262 (8)
C140.0650 (10)0.0488 (9)0.0645 (10)0.0082 (8)−0.0234 (8)−0.0247 (8)
C100.0859 (14)0.0962 (15)0.0755 (13)0.0283 (12)−0.0423 (12)−0.0388 (12)
Geometric parameters (Å, º) top
N2—C61.3730 (19)C12—H120.9300
N2—C111.3924 (19)C7—C81.531 (2)
N2—C71.4601 (19)C7—H7A0.9700
N1—O11.225 (2)C7—H7B0.9700
N1—O21.2290 (19)C5—H50.9300
N1—C11.458 (2)C15—C141.381 (2)
C11—C121.393 (2)C15—H150.9300
C11—C161.406 (2)C13—C141.391 (2)
C2—C11.380 (2)C13—H130.9300
C2—C31.387 (2)C8—C91.502 (2)
C2—H20.9300C8—H8A0.9700
C3—C61.418 (2)C8—H8B0.9700
C3—C161.442 (2)C9—C101.517 (2)
C6—C51.398 (2)C9—H9A0.9700
C1—C41.391 (2)C9—H9B0.9700
C16—C151.393 (2)C14—H140.9300
C4—C51.374 (2)C10—H10A0.9600
C4—H40.9300C10—H10B0.9600
C12—C131.376 (2)C10—H10C0.9600
C6—N2—C11108.59 (12)N2—C7—H7B109.0
C6—N2—C7126.97 (13)C8—C7—H7B109.0
C11—N2—C7124.40 (13)H7A—C7—H7B107.8
O1—N1—O2123.01 (15)C4—C5—C6118.11 (14)
O1—N1—C1118.64 (15)C4—C5—H5120.9
O2—N1—C1118.35 (16)C6—C5—H5120.9
N2—C11—C12128.91 (14)C14—C15—C16118.65 (15)
N2—C11—C16109.18 (13)C14—C15—H15120.7
C12—C11—C16121.91 (14)C16—C15—H15120.7
C1—C2—C3117.88 (14)C12—C13—C14122.02 (15)
C1—C2—H2121.1C12—C13—H13119.0
C3—C2—H2121.1C14—C13—H13119.0
C2—C3—C6119.72 (13)C9—C8—C7114.26 (14)
C2—C3—C16133.72 (14)C9—C8—H8A108.7
C6—C3—C16106.56 (12)C7—C8—H8A108.7
N2—C6—C5129.60 (14)C9—C8—H8B108.7
N2—C6—C3109.16 (13)C7—C8—H8B108.7
C5—C6—C3121.24 (14)H8A—C8—H8B107.6
C2—C1—C4122.71 (14)C8—C9—C10111.91 (15)
C2—C1—N1118.87 (14)C8—C9—H9A109.2
C4—C1—N1118.42 (15)C10—C9—H9A109.2
C15—C16—C11119.52 (14)C8—C9—H9B109.2
C15—C16—C3133.98 (14)C10—C9—H9B109.2
C11—C16—C3106.50 (12)H9A—C9—H9B107.9
C5—C4—C1120.34 (15)C15—C14—C13120.85 (15)
C5—C4—H4119.8C15—C14—H14119.6
C1—C4—H4119.8C13—C14—H14119.6
C13—C12—C11117.05 (15)C9—C10—H10A109.5
C13—C12—H12121.5C9—C10—H10B109.5
C11—C12—H12121.5H10A—C10—H10B109.5
N2—C7—C8112.79 (13)C9—C10—H10C109.5
N2—C7—H7A109.0H10A—C10—H10C109.5
C8—C7—H7A109.0H10B—C10—H10C109.5
C6—N2—C11—C12179.28 (14)N2—C11—C16—C30.38 (15)
C7—N2—C11—C121.2 (2)C12—C11—C16—C3−179.68 (13)
C6—N2—C11—C16−0.79 (16)C2—C3—C16—C15−0.2 (3)
C7—N2—C11—C16−178.82 (13)C6—C3—C16—C15−179.70 (15)
C1—C2—C3—C60.4 (2)C2—C3—C16—C11179.60 (15)
C1—C2—C3—C16−179.01 (14)C6—C3—C16—C110.15 (15)
C11—N2—C6—C5−179.23 (14)C2—C1—C4—C50.4 (2)
C7—N2—C6—C5−1.3 (2)N1—C1—C4—C5−178.75 (14)
C11—N2—C6—C30.89 (16)N2—C11—C12—C13−179.99 (14)
C7—N2—C6—C3178.85 (13)C16—C11—C12—C130.1 (2)
C2—C3—C6—N2179.82 (12)C6—N2—C7—C8−99.63 (18)
C16—C3—C6—N2−0.64 (15)C11—N2—C7—C878.03 (18)
C2—C3—C6—C5−0.1 (2)C1—C4—C5—C60.0 (2)
C16—C3—C6—C5179.47 (13)N2—C6—C5—C4−179.98 (14)
C3—C2—C1—C4−0.5 (2)C3—C6—C5—C4−0.1 (2)
C3—C2—C1—N1178.57 (13)C11—C16—C15—C14−0.1 (2)
O1—N1—C1—C24.2 (2)C3—C16—C15—C14179.74 (15)
O2—N1—C1—C2−175.23 (14)C11—C12—C13—C14−0.5 (2)
O1—N1—C1—C4−176.61 (15)N2—C7—C8—C963.5 (2)
O2—N1—C1—C43.9 (2)C7—C8—C9—C10−175.61 (15)
N2—C11—C16—C15−179.74 (12)C16—C15—C14—C13−0.3 (2)
C12—C11—C16—C150.2 (2)C12—C13—C14—C150.6 (3)
 

Acknowledgements

We are grateful to the Natural Science Foundation of Anhui Province (1508085QB41) and the key discipline construction of Anhui Science and Technology University (grant No. AKZDXK2015A01) for supporting this study.

References

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ISSN: 2414-3146
Volume 1| Part 11| November 2016| x161776
https://doi.org/10.1107/S2414314616017764
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