organic compounds
9-[4-(Azidomethyl)phenyl]-9H-carbazole-3-carbonitrile
aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India, bPrincipal, Kundavai Nachiyar Govt College for Women, Thanjavur 613 007, India, cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, dDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist., Chennai 603 203, Tamil Nadu, India, and eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
*Correspondence e-mail: phdguna@gmail.com, crystallography2010@gmail.com
In the title compound C20H13N5, the dihedral angle between the carbazole ring system (r.m.s. deviation = 0.027 Å) and the pendant benzene ring is 55.08 (6)°. One of the azide N atoms is disordered over two positions in a 0.65 (2):0.35 (2) ratio. In the crystal, aromatic π–π stacking is observed [minimum centroid–centroid separation = 3.6499 (13) Å] as well as inversion-dimers connected by pairs of weak C—H⋯π interactions.
CCDC reference: 982430
Related literature
For the biological activity of carbazole derivatives, see: Ramsewak et al. (1999); Tachibana et al. (2001); Itoigawa et al. (2000); Friend et al. (1999). For related structures, see: Velmurugan et al. (2010); Ramathilagam et al. (2011)
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 982430
10.1107/S1600536814001391/hb7185sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001391/hb7185Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001391/hb7185Isup3.cml
9-(4-(bromomethyl)phenyl)-9H-carbazole-3-carbonitrile (1.0 mmol, 1.0 equiv) was dissolved in acetone/water (4:1, 8 ml). NaN3 (1.5 mmol, 1.5 equiv.) was added and the mixture was heated at 60 ° C for 5 h. The reaction mixture was cooled to room temperature, acetone was evaporated and the reaction mixture was diluted with H2O (100 ml) and extracted with CHCl3 (2 x 100 ml). The organic layer was washed with saturated NaCl (50 ml), dried over Na2SO4 and evaporated gave 9-(4-(azidomethyl)phenyl) -9H-carbazole-3-carbonitrile as pale yellow blocks with a yield of 84% and melting point 148 ° C.
In azidomethyl group one of the nitrogen atom is disordered over two position. The site occupancy factors of disordered nitrogen atoms were refined as N3 = 0.35 (2) and N3A = 0.65 (2) during anisotropic
The N3A—N4 bond distance was restrained to be 1.1500 (1) Å. The atom N3A exhibited elongation of the thermal elipsoid and have been restrained (ISOR) to be more isotropic. The components of the anisotropic displacement parameters in direction of the bond N3—N4 and N4—N5, were restrained to be equal within an effective standard deviation of 0.001 using the DELU command in SHELXL (Sheldrick, 2008). H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2.Carbazole derivatives possess antioxidative (Tachibana et al., 2001), antitumor (Itoigawa et al., 2000), anti-inflammatory and antimutagenic (Ramsewak et al., 1999)activities. These derivatives also exhibit electroactivity and luminescence properties and are considered to be potential candidates for electronics such as colour display, organic semiconductor lasers and solar cells (Friend et al., 1999).
The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure(Velmurugan et al., 2010; Ramathilagam et al., 2011). Phenyl ring makes the dihedral angle of 55.08 (6) ° with the carbazole ring system. In azidomethyl group one of the nitrogen atom is disordered over two position with site occupancies of 0.35 (2) and 0.65 (2). The sum of bond angles around the atom N1 [359.81 (17) °] indicates sp2 hybridized. The crystal packing features weak C—H···π [C14—H14···Cg3(1 - x, 1 - y, -z) distance of 3.672 (7) Å, (Cg3 and is the centroid of the ring defined by the atoms C7—C12)] interactions.
For the biological activity of carbazole derivatives, see: Ramsewak et al. (1999); Tachibana et al. (2001); Itoigawa et al. (2000); Friend et al. (1999). For related structures, see: Velmurugan et al. (2010); Ramathilagam et al. (2011)
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms. |
C20H13N5 | F(000) = 672 |
Mr = 323.35 | Dx = 1.304 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4076 reflections |
a = 9.8457 (2) Å | θ = 2.0–28.3° |
b = 8.4032 (2) Å | µ = 0.08 mm−1 |
c = 19.9127 (5) Å | T = 295 K |
β = 90.970 (2)° | Block, pale yellow |
V = 1647.25 (7) Å3 | 0.25 × 0.20 × 0.20 mm |
Z = 4 |
Bruker kappa APEXII CCD diffractometer | 4076 independent reflections |
Radiation source: fine-focus sealed tube | 2676 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 0 pixels mm-1 | θmax = 28.3°, θmin = 2.1° |
ω and φ scans | h = −12→13 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −10→11 |
Tmin = 0.958, Tmax = 0.984 | l = −26→26 |
15375 measured reflections |
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.230 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.1219P)2 + 0.4961P] where P = (Fo2 + 2Fc2)/3 |
4076 reflections | (Δ/σ)max < 0.001 |
236 parameters | Δρmax = 0.67 e Å−3 |
10 restraints | Δρmin = −0.32 e Å−3 |
C20H13N5 | V = 1647.25 (7) Å3 |
Mr = 323.35 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.8457 (2) Å | µ = 0.08 mm−1 |
b = 8.4032 (2) Å | T = 295 K |
c = 19.9127 (5) Å | 0.25 × 0.20 × 0.20 mm |
β = 90.970 (2)° |
Bruker kappa APEXII CCD diffractometer | 4076 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2676 reflections with I > 2σ(I) |
Tmin = 0.958, Tmax = 0.984 | Rint = 0.023 |
15375 measured reflections |
R[F2 > 2σ(F2)] = 0.065 | 10 restraints |
wR(F2) = 0.230 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.67 e Å−3 |
4076 reflections | Δρmin = −0.32 e Å−3 |
236 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.1427 (2) | 0.6443 (3) | −0.02437 (10) | 0.0462 (5) | |
C2 | 0.0810 (2) | 0.7908 (3) | −0.03579 (11) | 0.0532 (5) | |
H2 | 0.0891 | 0.8728 | −0.0046 | 0.064* | |
C3 | 0.0079 (3) | 0.8108 (3) | −0.09424 (12) | 0.0584 (6) | |
H3 | −0.0355 | 0.9073 | −0.1025 | 0.070* | |
C4 | −0.0026 (2) | 0.6891 (3) | −0.14171 (11) | 0.0554 (6) | |
C5 | 0.0600 (2) | 0.5431 (3) | −0.13083 (10) | 0.0502 (5) | |
H5 | 0.0533 | 0.4627 | −0.1628 | 0.060* | |
C6 | 0.1326 (2) | 0.5191 (2) | −0.07139 (10) | 0.0453 (5) | |
C7 | 0.2076 (2) | 0.3867 (3) | −0.04382 (11) | 0.0473 (5) | |
C8 | 0.2302 (2) | 0.2308 (3) | −0.06541 (12) | 0.0541 (5) | |
H8 | 0.1961 | 0.1962 | −0.1067 | 0.065* | |
C9 | 0.3039 (2) | 0.1295 (3) | −0.02440 (13) | 0.0602 (6) | |
H9 | 0.3202 | 0.0258 | −0.0384 | 0.072* | |
C10 | 0.3538 (3) | 0.1802 (3) | 0.03750 (13) | 0.0638 (6) | |
H10 | 0.4019 | 0.1089 | 0.0646 | 0.077* | |
C11 | 0.3343 (3) | 0.3342 (3) | 0.06016 (12) | 0.0591 (6) | |
H11 | 0.3687 | 0.3677 | 0.1016 | 0.071* | |
C12 | 0.2609 (2) | 0.4363 (3) | 0.01842 (11) | 0.0491 (5) | |
C13 | 0.2663 (2) | 0.6895 (2) | 0.08503 (10) | 0.0470 (5) | |
C14 | 0.4037 (2) | 0.7025 (3) | 0.09936 (12) | 0.0559 (6) | |
H14 | 0.4666 | 0.6511 | 0.0726 | 0.067* | |
C15 | 0.4469 (3) | 0.7928 (3) | 0.15393 (13) | 0.0607 (6) | |
H15 | 0.5393 | 0.8000 | 0.1640 | 0.073* | |
C16 | 0.3556 (3) | 0.8719 (3) | 0.19349 (11) | 0.0600 (6) | |
C17 | 0.2184 (3) | 0.8588 (3) | 0.17812 (11) | 0.0585 (6) | |
H17 | 0.1556 | 0.9119 | 0.2044 | 0.070* | |
C18 | 0.1733 (2) | 0.7679 (3) | 0.12418 (11) | 0.0535 (5) | |
H18 | 0.0809 | 0.7596 | 0.1144 | 0.064* | |
C19 | −0.0782 (3) | 0.7148 (3) | −0.20322 (13) | 0.0720 (7) | |
C20 | 0.4028 (4) | 0.9678 (4) | 0.25333 (15) | 0.0909 (10) | |
H20A | 0.4985 | 0.9911 | 0.2479 | 0.109* | |
H20B | 0.3548 | 1.0686 | 0.2523 | 0.109* | |
N1 | 0.22210 (19) | 0.5936 (2) | 0.02970 (9) | 0.0501 (5) | |
N2 | −0.1372 (4) | 0.7353 (4) | −0.25201 (14) | 0.1079 (10) | |
N3 | 0.4560 (12) | 0.8595 (18) | 0.3064 (5) | 0.106 (4) | 0.35 (2) |
N3A | 0.3867 (14) | 0.9011 (9) | 0.3169 (3) | 0.134 (4) | 0.65 (2) |
N4 | 0.3659 (4) | 0.7676 (7) | 0.32487 (16) | 0.1170 (13) | |
N5 | 0.3230 (6) | 0.6426 (7) | 0.3378 (3) | 0.186 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0527 (11) | 0.0444 (11) | 0.0414 (10) | −0.0050 (9) | −0.0002 (8) | 0.0002 (8) |
C2 | 0.0671 (13) | 0.0423 (12) | 0.0502 (12) | −0.0001 (10) | −0.0010 (10) | −0.0016 (9) |
C3 | 0.0714 (15) | 0.0498 (13) | 0.0538 (12) | 0.0052 (11) | −0.0009 (11) | 0.0063 (10) |
C4 | 0.0656 (14) | 0.0580 (14) | 0.0425 (11) | −0.0009 (10) | −0.0018 (10) | 0.0077 (9) |
C5 | 0.0591 (12) | 0.0503 (12) | 0.0413 (10) | −0.0080 (9) | 0.0015 (9) | −0.0012 (9) |
C6 | 0.0499 (11) | 0.0430 (11) | 0.0431 (10) | −0.0062 (8) | 0.0037 (8) | −0.0002 (8) |
C7 | 0.0513 (11) | 0.0444 (11) | 0.0462 (11) | −0.0047 (8) | 0.0020 (8) | −0.0014 (8) |
C8 | 0.0584 (12) | 0.0478 (12) | 0.0561 (13) | −0.0058 (10) | 0.0016 (10) | −0.0078 (10) |
C9 | 0.0661 (14) | 0.0428 (12) | 0.0717 (15) | 0.0011 (10) | 0.0036 (12) | −0.0033 (10) |
C10 | 0.0712 (15) | 0.0511 (14) | 0.0688 (15) | 0.0082 (11) | −0.0046 (12) | 0.0065 (11) |
C11 | 0.0697 (14) | 0.0531 (14) | 0.0540 (13) | 0.0034 (11) | −0.0085 (11) | 0.0006 (10) |
C12 | 0.0547 (11) | 0.0431 (11) | 0.0496 (11) | −0.0034 (9) | 0.0000 (9) | −0.0013 (9) |
C13 | 0.0587 (12) | 0.0416 (11) | 0.0405 (10) | −0.0067 (9) | −0.0041 (8) | −0.0005 (8) |
C14 | 0.0579 (13) | 0.0554 (13) | 0.0543 (12) | −0.0036 (10) | 0.0004 (10) | −0.0017 (10) |
C15 | 0.0632 (14) | 0.0579 (14) | 0.0606 (13) | −0.0114 (11) | −0.0123 (11) | 0.0004 (11) |
C16 | 0.0848 (17) | 0.0479 (13) | 0.0468 (12) | −0.0102 (11) | −0.0128 (11) | −0.0002 (9) |
C17 | 0.0772 (16) | 0.0525 (13) | 0.0458 (12) | 0.0007 (11) | 0.0028 (11) | −0.0061 (10) |
C18 | 0.0587 (12) | 0.0504 (13) | 0.0512 (12) | −0.0028 (10) | −0.0015 (10) | −0.0019 (10) |
C19 | 0.096 (2) | 0.0680 (17) | 0.0518 (14) | 0.0063 (14) | −0.0078 (13) | 0.0073 (12) |
C20 | 0.123 (3) | 0.083 (2) | 0.0659 (18) | −0.0031 (18) | −0.0312 (17) | −0.0208 (15) |
N1 | 0.0608 (11) | 0.0419 (10) | 0.0472 (10) | 0.0001 (8) | −0.0076 (8) | −0.0047 (7) |
N2 | 0.157 (3) | 0.102 (2) | 0.0629 (15) | 0.021 (2) | −0.0350 (17) | 0.0106 (15) |
N3 | 0.074 (5) | 0.200 (7) | 0.044 (5) | 0.028 (5) | −0.013 (3) | −0.012 (5) |
N3A | 0.157 (8) | 0.172 (6) | 0.073 (3) | −0.066 (5) | 0.018 (4) | −0.039 (4) |
N4 | 0.112 (3) | 0.176 (4) | 0.0636 (17) | 0.046 (3) | 0.0171 (17) | 0.027 (2) |
N5 | 0.194 (5) | 0.181 (4) | 0.187 (5) | 0.079 (3) | 0.087 (4) | 0.105 (4) |
C1—N1 | 1.387 (3) | C12—N1 | 1.395 (3) |
C1—C2 | 1.389 (3) | C13—C18 | 1.380 (3) |
C1—C6 | 1.411 (3) | C13—C14 | 1.382 (3) |
C2—C3 | 1.368 (3) | C13—N1 | 1.427 (3) |
C2—H2 | 0.9300 | C14—C15 | 1.386 (3) |
C3—C4 | 1.396 (3) | C14—H14 | 0.9300 |
C3—H3 | 0.9300 | C15—C16 | 1.377 (4) |
C4—C5 | 1.389 (3) | C15—H15 | 0.9300 |
C4—C19 | 1.439 (3) | C16—C17 | 1.385 (4) |
C5—C6 | 1.387 (3) | C16—C20 | 1.505 (3) |
C5—H5 | 0.9300 | C17—C18 | 1.385 (3) |
C6—C7 | 1.439 (3) | C17—H17 | 0.9300 |
C7—C8 | 1.397 (3) | C18—H18 | 0.9300 |
C7—C12 | 1.401 (3) | C19—N2 | 1.137 (4) |
C8—C9 | 1.378 (3) | C20—N3A | 1.397 (8) |
C8—H8 | 0.9300 | C20—N3 | 1.483 (11) |
C9—C10 | 1.387 (4) | C20—H20A | 0.9700 |
C9—H9 | 0.9300 | C20—H20B | 0.9700 |
C10—C11 | 1.385 (4) | N3—N4 | 1.237 (14) |
C10—H10 | 0.9300 | N3A—N4 | 1.1513 (10) |
C11—C12 | 1.389 (3) | N4—N5 | 1.163 (7) |
C11—H11 | 0.9300 | ||
N1—C1—C2 | 129.68 (19) | C18—C13—C14 | 120.1 (2) |
N1—C1—C6 | 108.53 (18) | C18—C13—N1 | 120.60 (19) |
C2—C1—C6 | 121.78 (19) | C14—C13—N1 | 119.3 (2) |
C3—C2—C1 | 118.0 (2) | C13—C14—C15 | 119.5 (2) |
C3—C2—H2 | 121.0 | C13—C14—H14 | 120.3 |
C1—C2—H2 | 121.0 | C15—C14—H14 | 120.3 |
C2—C3—C4 | 121.2 (2) | C16—C15—C14 | 121.2 (2) |
C2—C3—H3 | 119.4 | C16—C15—H15 | 119.4 |
C4—C3—H3 | 119.4 | C14—C15—H15 | 119.4 |
C5—C4—C3 | 120.9 (2) | C15—C16—C17 | 118.6 (2) |
C5—C4—C19 | 119.2 (2) | C15—C16—C20 | 121.1 (3) |
C3—C4—C19 | 119.9 (2) | C17—C16—C20 | 120.3 (3) |
C6—C5—C4 | 118.9 (2) | C16—C17—C18 | 120.9 (2) |
C6—C5—H5 | 120.6 | C16—C17—H17 | 119.5 |
C4—C5—H5 | 120.6 | C18—C17—H17 | 119.5 |
C5—C6—C1 | 119.2 (2) | C13—C18—C17 | 119.6 (2) |
C5—C6—C7 | 133.7 (2) | C13—C18—H18 | 120.2 |
C1—C6—C7 | 107.10 (18) | C17—C18—H18 | 120.2 |
C8—C7—C12 | 119.5 (2) | N2—C19—C4 | 179.6 (4) |
C8—C7—C6 | 133.7 (2) | N3A—C20—C16 | 117.7 (3) |
C12—C7—C6 | 106.80 (19) | N3—C20—C16 | 109.6 (6) |
C9—C8—C7 | 118.8 (2) | N3A—C20—H20A | 107.9 |
C9—C8—H8 | 120.6 | N3—C20—H20A | 82.6 |
C7—C8—H8 | 120.6 | C16—C20—H20A | 107.9 |
C8—C9—C10 | 120.8 (2) | N3A—C20—H20B | 107.9 |
C8—C9—H9 | 119.6 | N3—C20—H20B | 135.8 |
C10—C9—H9 | 119.6 | C16—C20—H20B | 107.9 |
C11—C10—C9 | 121.8 (2) | H20A—C20—H20B | 107.2 |
C11—C10—H10 | 119.1 | C1—N1—C12 | 108.59 (17) |
C9—C10—H10 | 119.1 | C1—N1—C13 | 125.89 (18) |
C10—C11—C12 | 117.1 (2) | C12—N1—C13 | 125.34 (18) |
C10—C11—H11 | 121.4 | N4—N3—C20 | 110.4 (7) |
C12—C11—H11 | 121.4 | N4—N3A—C20 | 122.6 (6) |
C11—C12—N1 | 129.1 (2) | N3A—N4—N5 | 167.6 (8) |
C11—C12—C7 | 121.9 (2) | N5—N4—N3 | 153.5 (8) |
N1—C12—C7 | 108.97 (19) | ||
N1—C1—C2—C3 | 179.5 (2) | C14—C15—C16—C17 | 0.5 (4) |
C6—C1—C2—C3 | 0.7 (3) | C14—C15—C16—C20 | 179.1 (2) |
C1—C2—C3—C4 | −1.1 (4) | C15—C16—C17—C18 | 0.1 (4) |
C2—C3—C4—C5 | 0.5 (4) | C20—C16—C17—C18 | −178.4 (2) |
C2—C3—C4—C19 | −178.9 (2) | C14—C13—C18—C17 | −0.4 (3) |
C3—C4—C5—C6 | 0.6 (3) | N1—C13—C18—C17 | 179.3 (2) |
C19—C4—C5—C6 | −180.0 (2) | C16—C17—C18—C13 | −0.2 (3) |
C4—C5—C6—C1 | −1.0 (3) | C15—C16—C20—N3A | −103.0 (8) |
C4—C5—C6—C7 | 179.6 (2) | C17—C16—C20—N3A | 75.6 (8) |
N1—C1—C6—C5 | −178.63 (18) | C15—C16—C20—N3 | −69.1 (6) |
C2—C1—C6—C5 | 0.4 (3) | C17—C16—C20—N3 | 109.5 (6) |
N1—C1—C6—C7 | 0.9 (2) | C2—C1—N1—C12 | 180.0 (2) |
C2—C1—C6—C7 | 179.95 (19) | C6—C1—N1—C12 | −1.1 (2) |
C5—C6—C7—C8 | −3.3 (4) | C2—C1—N1—C13 | −4.8 (4) |
C1—C6—C7—C8 | 177.3 (2) | C6—C1—N1—C13 | 174.15 (19) |
C5—C6—C7—C12 | 179.1 (2) | C11—C12—N1—C1 | −176.2 (2) |
C1—C6—C7—C12 | −0.4 (2) | C7—C12—N1—C1 | 0.9 (2) |
C12—C7—C8—C9 | 0.5 (3) | C11—C12—N1—C13 | 8.5 (4) |
C6—C7—C8—C9 | −176.9 (2) | C7—C12—N1—C13 | −174.42 (19) |
C7—C8—C9—C10 | 0.6 (4) | C18—C13—N1—C1 | 57.2 (3) |
C8—C9—C10—C11 | −1.1 (4) | C14—C13—N1—C1 | −123.1 (2) |
C9—C10—C11—C12 | 0.6 (4) | C18—C13—N1—C12 | −128.3 (2) |
C10—C11—C12—N1 | 177.2 (2) | C14—C13—N1—C12 | 51.3 (3) |
C10—C11—C12—C7 | 0.5 (4) | N3A—C20—N3—N4 | 50.2 (7) |
C8—C7—C12—C11 | −1.0 (3) | C16—C20—N3—N4 | −61.0 (11) |
C6—C7—C12—C11 | 177.0 (2) | N3—C20—N3A—N4 | −66.7 (13) |
C8—C7—C12—N1 | −178.34 (19) | C16—C20—N3A—N4 | 16.2 (17) |
C6—C7—C12—N1 | −0.3 (2) | C20—N3A—N4—N5 | −118 (3) |
C18—C13—C14—C15 | 1.0 (3) | C20—N3A—N4—N3 | 68.5 (11) |
N1—C13—C14—C15 | −178.6 (2) | C20—N3—N4—N3A | −51.9 (9) |
C13—C14—C15—C16 | −1.1 (4) | C20—N3—N4—N5 | 131.1 (12) |
Cg3 is the centroid of the C7–C12 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···Cg3i | 0.93 | 2.91 | 3.673 (2) | 140 |
Symmetry code: (i) −x+1, −y+1, −z. |
Cg3 is the centroid of the C7–C12 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···Cg3i | 0.93 | 2.91 | 3.673 (2) | 140 |
Symmetry code: (i) −x+1, −y+1, −z. |
Acknowledgements
CR acknowledge AMET University management, India, for their kind support.
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Carbazole derivatives possess antioxidative (Tachibana et al., 2001), antitumor (Itoigawa et al., 2000), anti-inflammatory and antimutagenic (Ramsewak et al., 1999)activities. These derivatives also exhibit electroactivity and luminescence properties and are considered to be potential candidates for electronics such as colour display, organic semiconductor lasers and solar cells (Friend et al., 1999).
The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure(Velmurugan et al., 2010; Ramathilagam et al., 2011). Phenyl ring makes the dihedral angle of 55.08 (6) ° with the carbazole ring system. In azidomethyl group one of the nitrogen atom is disordered over two position with site occupancies of 0.35 (2) and 0.65 (2). The sum of bond angles around the atom N1 [359.81 (17) °] indicates sp2 hybridized. The crystal packing features weak C—H···π [C14—H14···Cg3(1 - x, 1 - y, -z) distance of 3.672 (7) Å, (Cg3 and is the centroid of the ring defined by the atoms C7—C12)] interactions.