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access9-(2-Bromoethyl)-9H-carbazole
aSchool of Chemistry and Life Science, Changchun University of Technology, Changchun 130012, People's Republic of China
*Correspondence e-mail: lidongfeng@mail.ccut.edu.cn
In the title compound, C14H12BrN, the fused-ring system is slightly buckled as its two benzene rings are inclined to one another by 3.41 (14)°.
Related literature
For the synthesis, see: Huang et al. (2004![[Huang, X. F., Zhong, S. Z., Yan, X. Z., Ke, X. J., Srisanit, N. & Wang, M. R. (2004). Synth. Met. 140, 79-86.]](../../../../../../logos/arrows/e_arr.gif "Huang, X. F., Zhong, S. Z., Yan, X. Z., Ke, X. J., Srisanit, N. & Wang, M. R. (2004). Synth. Met. 140, 79-86.")
). For a similar structure, see: Aravindan et al. (2003).
![[Scheme 1]](ng5265scheme1.gif)
Experimental
Crystal data
|
Data collection: RAPID-AUTO (Rigaku, 1998); cell RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002); 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: SHELXL97.
Supporting information
contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812024397/ng5265sup1.cif
Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812024397/ng5265Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812024397/ng5265Isup3.cml
The title compound was prepared according to the literature (Huang et al. 2004). Single crystals suitable were prepared by slow evaporation of a dichloromethane solution of the compoundat room temperature.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 and 0.97 Å) and were included in the in the riding model with Uiso(H) = 1.2 Ueq(C). The (-2 5 5) was omitted owing to bad disagreement.
Carozole and its derivatives are an important type of nitrogen-containing aromatic These special structure of carbazole compounds endow their distinct various functions as well as wide potential applications. In this paper, we report the of the title compound.
The molecular structure of tiltle compound, C14H12BrN, as shown in Fig.1, all bond lengths and angles are in the normal ranges and are comparable with a reported compounnd (Aravindan et al. 2003). The dihedral angel of the two benzene rings is 3.41 (14) °. stablize the crystal structure.
For the synthesis, see: Huang et al. (2004). For a similar structure, see: Aravindan et al. (2003).
Data collection: RAPID-AUTO (Rigaku, 1998); cell RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); 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: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./ng5265fig1thm.gif) | Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probalility level. |
| C14H12BrN | F(000) = 552 |
| Mr = 274.16 | Dx = 1.577 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 8078 reflections |
| a = 5.417 (3) Å | θ = 3.3–27.5° |
| b = 12.254 (6) Å | µ = 3.53 mm−1 |
| c = 17.505 (11) Å | T = 288 K |
| β = 96.46 (3)° | Block, colorless |
| V = 1154.6 (11) Å3 | 0.16 × 0.15 × 0.13 mm |
| Z = 4 |
| Rigaku R-AXIS RAPID diffractometer | 2630 independent reflections |
| Radiation source: fine-focus sealed tube | 2093 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.039 |
| ω scans | θmax = 27.5°, θmin = 3.3° |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −6→7 |
| Tmin = 0.599, Tmax = 0.657 | k = −15→15 |
| 10873 measured reflections | l = −22→22 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.082 | H-atom parameters constrained |
| S = 1.02 | w = 1/[σ2(Fo2) + (0.0394P)2 + 0.3164P] where P = (Fo2 + 2Fc2)/3 |
| 2630 reflections | (Δ/σ)max = 0.007 |
| 145 parameters | Δρmax = 0.23 e Å−3 |
| 0 restraints | Δρmin = −0.59 e Å−3 |
| C14H12BrN | V = 1154.6 (11) Å3 |
| Mr = 274.16 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 5.417 (3) Å | µ = 3.53 mm−1 |
| b = 12.254 (6) Å | T = 288 K |
| c = 17.505 (11) Å | 0.16 × 0.15 × 0.13 mm |
| β = 96.46 (3)° |
| Rigaku R-AXIS RAPID diffractometer | 2630 independent reflections |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2093 reflections with I > 2σ(I) |
| Tmin = 0.599, Tmax = 0.657 | Rint = 0.039 |
| 10873 measured reflections |
| R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
| wR(F2) = 0.082 | H-atom parameters constrained |
| S = 1.02 | Δρmax = 0.23 e Å−3 |
| 2630 reflections | Δρmin = −0.59 e Å−3 |
| 145 parameters |
Experimental. (See detailed section in the paper) |
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 | ||
| Br1 | 0.25417 (5) | 1.06970 (2) | 0.430911 (16) | 0.05611 (12) | |
| C1 | 0.0265 (4) | 0.88648 (17) | 0.22679 (12) | 0.0350 (4) | |
| C2 | −0.1470 (4) | 0.94431 (18) | 0.17824 (14) | 0.0420 (5) | |
| H2 | −0.2717 | 0.9847 | 0.1974 | 0.050* | |
| C3 | −0.1273 (5) | 0.9395 (2) | 0.10030 (14) | 0.0506 (6) | |
| H3 | −0.2424 | 0.9766 | 0.0664 | 0.061* | |
| C4 | 0.0610 (5) | 0.8802 (2) | 0.07141 (14) | 0.0504 (6) | |
| H4 | 0.0706 | 0.8793 | 0.0187 | 0.060* | |
| C5 | 0.2328 (4) | 0.82325 (19) | 0.11943 (13) | 0.0446 (5) | |
| H5 | 0.3591 | 0.7846 | 0.0997 | 0.054* | |
| C6 | 0.2147 (4) | 0.82425 (16) | 0.19839 (12) | 0.0356 (4) | |
| C7 | 0.3499 (4) | 0.77144 (17) | 0.26390 (13) | 0.0365 (5) | |
| C8 | 0.5493 (4) | 0.69878 (19) | 0.27313 (15) | 0.0473 (6) | |
| H8 | 0.6248 | 0.6755 | 0.2309 | 0.057* | |
| C9 | 0.6322 (5) | 0.6623 (2) | 0.34564 (18) | 0.0572 (7) | |
| H9 | 0.7654 | 0.6140 | 0.3522 | 0.069* | |
| C10 | 0.5209 (5) | 0.6961 (2) | 0.40933 (16) | 0.0546 (6) | |
| H10 | 0.5813 | 0.6698 | 0.4577 | 0.066* | |
| C11 | 0.3225 (4) | 0.76790 (19) | 0.40274 (14) | 0.0465 (5) | |
| H11 | 0.2484 | 0.7903 | 0.4455 | 0.056* | |
| C12 | 0.2387 (4) | 0.80512 (17) | 0.32906 (13) | 0.0357 (4) | |
| C13 | −0.1196 (4) | 0.92796 (18) | 0.35461 (14) | 0.0417 (5) | |
| H13A | −0.1073 | 0.8900 | 0.4035 | 0.050* | |
| H13B | −0.2893 | 0.9207 | 0.3308 | 0.050* | |
| C14 | −0.0643 (4) | 1.04724 (19) | 0.36924 (15) | 0.0466 (5) | |
| H14A | −0.1951 | 1.0790 | 0.3956 | 0.056* | |
| H14B | −0.0631 | 1.0846 | 0.3204 | 0.056* | |
| N1 | 0.0445 (3) | 0.87583 (15) | 0.30599 (10) | 0.0369 (4) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.05008 (16) | 0.06487 (19) | 0.05276 (18) | −0.01404 (11) | 0.00307 (12) | −0.00812 (12) |
| C1 | 0.0349 (10) | 0.0342 (10) | 0.0358 (11) | −0.0048 (8) | 0.0038 (8) | −0.0010 (9) |
| C2 | 0.0387 (11) | 0.0423 (12) | 0.0441 (13) | 0.0013 (9) | 0.0002 (10) | 0.0007 (10) |
| C3 | 0.0585 (14) | 0.0479 (13) | 0.0417 (14) | −0.0059 (11) | −0.0106 (11) | 0.0088 (10) |
| C4 | 0.0685 (16) | 0.0497 (13) | 0.0322 (12) | −0.0103 (12) | 0.0017 (11) | 0.0014 (10) |
| C5 | 0.0533 (13) | 0.0427 (12) | 0.0394 (13) | −0.0039 (10) | 0.0117 (10) | −0.0061 (10) |
| C6 | 0.0370 (10) | 0.0337 (10) | 0.0363 (11) | −0.0056 (8) | 0.0055 (9) | −0.0034 (9) |
| C7 | 0.0352 (10) | 0.0339 (10) | 0.0401 (12) | −0.0040 (9) | 0.0035 (9) | −0.0024 (9) |
| C8 | 0.0413 (11) | 0.0414 (12) | 0.0589 (16) | 0.0033 (10) | 0.0042 (11) | −0.0067 (11) |
| C9 | 0.0480 (13) | 0.0421 (13) | 0.078 (2) | 0.0077 (11) | −0.0076 (13) | 0.0035 (13) |
| C10 | 0.0585 (14) | 0.0464 (13) | 0.0546 (16) | −0.0029 (12) | −0.0121 (12) | 0.0163 (12) |
| C11 | 0.0520 (12) | 0.0456 (12) | 0.0411 (13) | −0.0052 (11) | 0.0011 (11) | 0.0075 (10) |
| C12 | 0.0343 (10) | 0.0342 (10) | 0.0379 (11) | −0.0038 (8) | 0.0018 (8) | 0.0014 (9) |
| C13 | 0.0355 (10) | 0.0477 (13) | 0.0432 (13) | −0.0033 (9) | 0.0105 (9) | −0.0080 (10) |
| C14 | 0.0392 (11) | 0.0496 (13) | 0.0507 (15) | 0.0037 (10) | 0.0044 (10) | −0.0084 (11) |
| N1 | 0.0376 (9) | 0.0403 (9) | 0.0329 (9) | 0.0028 (8) | 0.0048 (7) | −0.0001 (8) |
| Br1—C14 | 1.949 (3) | C8—C9 | 1.373 (4) |
| C1—N1 | 1.385 (3) | C8—H8 | 0.9300 |
| C1—C2 | 1.389 (3) | C9—C10 | 1.389 (4) |
| C1—C6 | 1.408 (3) | C9—H9 | 0.9300 |
| C2—C3 | 1.382 (4) | C10—C11 | 1.383 (4) |
| C2—H2 | 0.9300 | C10—H10 | 0.9300 |
| C3—C4 | 1.392 (4) | C11—C12 | 1.395 (3) |
| C3—H3 | 0.9300 | C11—H11 | 0.9300 |
| C4—C5 | 1.372 (4) | C12—N1 | 1.387 (3) |
| C4—H4 | 0.9300 | C13—N1 | 1.447 (3) |
| C5—C6 | 1.397 (3) | C13—C14 | 1.508 (3) |
| C5—H5 | 0.9300 | C13—H13A | 0.9700 |
| C6—C7 | 1.443 (3) | C13—H13B | 0.9700 |
| C7—C8 | 1.395 (3) | C14—H14A | 0.9700 |
| C7—C12 | 1.410 (3) | C14—H14B | 0.9700 |
| N1—C1—C2 | 128.8 (2) | C10—C9—H9 | 119.4 |
| N1—C1—C6 | 109.29 (18) | C11—C10—C9 | 121.7 (2) |
| C2—C1—C6 | 121.8 (2) | C11—C10—H10 | 119.1 |
| C3—C2—C1 | 117.4 (2) | C9—C10—H10 | 119.1 |
| C3—C2—H2 | 121.3 | C10—C11—C12 | 117.0 (2) |
| C1—C2—H2 | 121.3 | C10—C11—H11 | 121.5 |
| C2—C3—C4 | 121.5 (2) | C12—C11—H11 | 121.5 |
| C2—C3—H3 | 119.3 | N1—C12—C11 | 129.1 (2) |
| C4—C3—H3 | 119.3 | N1—C12—C7 | 109.03 (19) |
| C5—C4—C3 | 121.1 (2) | C11—C12—C7 | 121.9 (2) |
| C5—C4—H4 | 119.5 | N1—C13—C14 | 113.85 (19) |
| C3—C4—H4 | 119.5 | N1—C13—H13A | 108.8 |
| C4—C5—C6 | 118.9 (2) | C14—C13—H13A | 108.8 |
| C4—C5—H5 | 120.5 | N1—C13—H13B | 108.8 |
| C6—C5—H5 | 120.5 | C14—C13—H13B | 108.8 |
| C5—C6—C1 | 119.2 (2) | H13A—C13—H13B | 107.7 |
| C5—C6—C7 | 134.2 (2) | C13—C14—Br1 | 112.18 (16) |
| C1—C6—C7 | 106.57 (18) | C13—C14—H14A | 109.2 |
| C8—C7—C12 | 119.3 (2) | Br1—C14—H14A | 109.2 |
| C8—C7—C6 | 134.1 (2) | C13—C14—H14B | 109.2 |
| C12—C7—C6 | 106.66 (18) | Br1—C14—H14B | 109.2 |
| C9—C8—C7 | 118.9 (2) | H14A—C14—H14B | 107.9 |
| C9—C8—H8 | 120.5 | C12—N1—C1 | 108.42 (17) |
| C7—C8—H8 | 120.5 | C12—N1—C13 | 126.90 (19) |
| C8—C9—C10 | 121.2 (2) | C1—N1—C13 | 124.65 (18) |
| C8—C9—H9 | 119.4 |
Experimental details
| Crystal data | |
| Chemical formula | C14H12BrN |
| Mr | 274.16 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 288 |
| a, b, c (Å) | 5.417 (3), 12.254 (6), 17.505 (11) |
| β (°) | 96.46 (3) |
| V (Å3) | 1154.6 (11) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 3.53 |
| Crystal size (mm) | 0.16 × 0.15 × 0.13 |
| Data collection | |
| Diffractometer | Rigaku R-AXIS RAPID |
| Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
| Tmin, Tmax | 0.599, 0.657 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 10873, 2630, 2093 |
| Rint | 0.039 |
| (sin θ/λ)max (Å−1) | 0.649 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.082, 1.02 |
| No. of reflections | 2630 |
| No. of parameters | 145 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.23, −0.59 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
The authors acknowledge financial support from the National Natural Science Foundation of Jilin Province (grant No. 20101548).
References
Aravindan, P. G., Selvanayagam, S., Yogavel, M., Velmurugan, D., Ravikumar, K., Nagarajan, N. & Perumal, P. T. (2003). Acta Cryst. E59, o1432–o1434. Web of Science CSD CrossRef IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Huang, X. F., Zhong, S. Z., Yan, X. Z., Ke, X. J., Srisanit, N. & Wang, M. R. (2004). Synth. Met. 140, 79-86. Web of Science CrossRef CAS Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
Carozole and its derivatives are an important type of nitrogen-containing aromatic heterocyclic compounds. These special structure of carbazole compounds endow their distinct various functions as well as wide potential applications. In this paper, we report the crystal structure of the title compound.
The molecular structure of tiltle compound, C14H12BrN, as shown in Fig.1, all bond lengths and angles are in the normal ranges and are comparable with a reported compounnd (Aravindan et al. 2003). The dihedral angel of the two benzene rings is 3.41 (14) °. Van der Waals forces stablize the crystal structure.