9-[4-(Azido-meth-yl)phen-yl]-9H-carbazole-3-carbo-nitrile.

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 inter-actions.

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

C20H13N5

M = 323.35

Monoclinic,

a = 9.8457 (2) Å

b = 8.4032 (2) Å

c = 19.9127 (5) Å

β = 90.970 (2)°

V = 1647.25 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.958, T max = 0.984

15375 measured reflections

4076 independent reflections

2676 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.230

S = 1.07

4076 reflections

236 parameters

10 restraints

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: 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.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814001391/hb7185sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001391/hb7185Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001391/hb7185Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

	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)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cg3i	0.93	2.91	3.673 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

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) .