7H-1-Benzofuro[2,3-b]carbazole.

In the title compound, C(18)H(11)NO, the carbazole and benzofuran rings are almost co-planar, making a dihedral angle of 3.31 (3)°. The crystal structure is stabilized by weak C-H⋯π inter-actions.

Related literature

For the biological activity of carbazole derivatives, see: Ramsewak et al. (1999 ▶); Diaz et al. (2002 ▶); Zhang et al. (2004 ▶). For the structures of closely related compounds, see: Chakkaravarthi et al. (2008a ▶,b ▶).

Experimental

Crystal data

C18H11NO

M = 257.28

Orthorhombic,

a = 26.087 (3) Å

b = 5.9585 (8) Å

c = 7.8146 (10) Å

V = 1214.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.24 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.979, T max = 0.983

6591 measured reflections

2700 independent reflections

2331 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.084

S = 1.05

2700 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

Absolute structure: Flack (1983 ▶), 1086 Friedel pairs

Flack parameter: 0.2 (15)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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) global, I. DOI: 10.1107/S1600536811039018/vm2122sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039018/vm2122Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039018/vm2122Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H11NO	F(000) = 536
Mr = 257.28	Dx = 1.407 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2246 reflections
a = 26.087 (3) Å	θ = 1.6–28.3°
b = 5.9585 (8) Å	µ = 0.09 mm−1
c = 7.8146 (10) Å	T = 295 K
V = 1214.7 (3) Å3	Block, colourless
Z = 4	0.24 × 0.22 × 0.20 mm

Bruker Kappa APEXII diffractometer	2700 independent reflections
Radiation source: fine-focus sealed tube	2331 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω and φ scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −33→34
Tmin = 0.979, Tmax = 0.983	k = −7→7
6591 measured reflections	l = −7→10

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033	w = 1/[σ2(Fo2) + (0.0437P)2 + 0.0541P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.084	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.13 e Å−3
2700 reflections	Δρmin = −0.13 e Å−3
182 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0083 (13)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1086 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.2 (15)

	x	y	z	Uiso*/Ueq
C1	0.95422 (6)	0.1951 (2)	0.5133 (2)	0.0412 (3)
C2	0.90187 (6)	0.2333 (3)	0.5252 (2)	0.0481 (4)
H2	0.8802	0.1313	0.5790	0.058*
C3	0.88330 (6)	0.4286 (3)	0.4541 (2)	0.0526 (4)
H3	0.8484	0.4587	0.4602	0.063*
C4	0.91550 (6)	0.5822 (3)	0.3733 (2)	0.0491 (4)
H4	0.9017	0.7122	0.3262	0.059*
C5	0.96747 (6)	0.5437 (2)	0.3624 (2)	0.0414 (3)
H5	0.9889	0.6474	0.3093	0.050*
C6	0.98745 (5)	0.3475 (2)	0.43203 (19)	0.0370 (3)
C7	1.03818 (5)	0.2503 (2)	0.43841 (19)	0.0366 (3)
C8	1.08582 (5)	0.3196 (2)	0.37727 (18)	0.0386 (3)
H8	1.0899	0.4576	0.3233	0.046*
C9	1.12697 (6)	0.1751 (2)	0.4000 (2)	0.0412 (3)
C10	1.11930 (6)	−0.0328 (2)	0.4815 (2)	0.0439 (4)
C11	1.07375 (6)	−0.1066 (3)	0.5477 (2)	0.0464 (4)
H11	1.0703	−0.2431	0.6042	0.056*
C12	1.03323 (6)	0.0405 (2)	0.5230 (2)	0.0403 (3)
C13	1.18108 (6)	0.1825 (3)	0.3568 (2)	0.0458 (4)
C14	1.21349 (6)	0.3394 (3)	0.2832 (2)	0.0525 (4)
H14	1.2009	0.4763	0.2444	0.063*
C15	1.26512 (6)	0.2873 (4)	0.2688 (3)	0.0617 (5)
H15	1.2874	0.3903	0.2192	0.074*
C16	1.28401 (7)	0.0836 (4)	0.3275 (3)	0.0666 (6)
H16	1.3188	0.0533	0.3169	0.080*
C17	1.25258 (7)	−0.0744 (3)	0.4009 (2)	0.0624 (5)
H17	1.2652	−0.2110	0.4403	0.075*
C18	1.20141 (6)	−0.0194 (3)	0.4131 (2)	0.0508 (4)
N1	0.98259 (5)	0.0150 (2)	0.57102 (18)	0.0443 (3)
H1	0.9706	−0.0965	0.6283	0.053*
O1	1.16449 (4)	−0.15463 (18)	0.48849 (17)	0.0557 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0493 (8)	0.0409 (7)	0.0336 (8)	−0.0090 (6)	−0.0002 (7)	−0.0032 (6)
C2	0.0450 (8)	0.0557 (9)	0.0434 (9)	−0.0134 (7)	0.0036 (7)	−0.0009 (8)
C3	0.0419 (8)	0.0659 (11)	0.0501 (10)	−0.0015 (7)	0.0016 (7)	−0.0052 (8)
C4	0.0511 (8)	0.0487 (8)	0.0474 (10)	0.0039 (7)	−0.0041 (8)	−0.0009 (8)
C5	0.0470 (7)	0.0383 (7)	0.0389 (8)	−0.0052 (6)	−0.0007 (7)	−0.0001 (6)
C6	0.0421 (7)	0.0381 (7)	0.0309 (7)	−0.0070 (5)	−0.0014 (6)	−0.0026 (6)
C7	0.0472 (7)	0.0313 (6)	0.0312 (7)	−0.0050 (6)	−0.0010 (6)	−0.0018 (6)
C8	0.0453 (7)	0.0350 (7)	0.0354 (8)	−0.0054 (6)	0.0002 (6)	0.0013 (6)
C9	0.0446 (7)	0.0402 (7)	0.0387 (9)	−0.0026 (6)	−0.0001 (6)	−0.0059 (6)
C10	0.0506 (8)	0.0386 (7)	0.0425 (9)	0.0033 (6)	−0.0040 (7)	−0.0048 (6)
C11	0.0596 (9)	0.0343 (7)	0.0452 (9)	−0.0023 (6)	−0.0016 (7)	0.0021 (7)
C12	0.0513 (8)	0.0347 (7)	0.0349 (8)	−0.0080 (6)	−0.0018 (6)	−0.0020 (6)
C13	0.0454 (8)	0.0519 (9)	0.0402 (9)	−0.0008 (7)	−0.0024 (7)	−0.0100 (7)
C14	0.0483 (9)	0.0633 (10)	0.0459 (10)	−0.0072 (7)	−0.0015 (8)	−0.0075 (8)
C15	0.0482 (9)	0.0839 (13)	0.0529 (12)	−0.0106 (9)	0.0043 (9)	−0.0151 (10)
C16	0.0451 (9)	0.0932 (15)	0.0616 (13)	0.0072 (10)	0.0007 (8)	−0.0240 (11)
C17	0.0550 (9)	0.0677 (10)	0.0645 (14)	0.0147 (9)	−0.0031 (9)	−0.0143 (10)
C18	0.0500 (8)	0.0540 (9)	0.0485 (11)	0.0034 (7)	−0.0025 (7)	−0.0109 (8)
N1	0.0505 (7)	0.0391 (6)	0.0432 (8)	−0.0106 (5)	0.0034 (6)	0.0053 (6)
O1	0.0558 (6)	0.0471 (6)	0.0643 (9)	0.0090 (5)	−0.0031 (6)	−0.0019 (5)

C1—N1	1.380 (2)	C10—C11	1.369 (2)
C1—C2	1.388 (2)	C10—O1	1.3856 (18)
C1—C6	1.407 (2)	C11—C12	1.387 (2)
C2—C3	1.377 (2)	C11—H11	0.9300
C2—H2	0.9300	C12—N1	1.3817 (19)
C3—C4	1.394 (2)	C13—C14	1.385 (2)
C3—H3	0.9300	C13—C18	1.386 (2)
C4—C5	1.378 (2)	C14—C15	1.387 (2)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.391 (2)	C15—C16	1.388 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.445 (2)	C16—C17	1.374 (3)
C7—C8	1.3940 (19)	C16—H16	0.9300
C7—C12	1.4202 (19)	C17—C18	1.378 (2)
C8—C9	1.388 (2)	C17—H17	0.9300
C8—H8	0.9300	C18—O1	1.387 (2)
C9—C10	1.407 (2)	N1—H1	0.8600
C9—C13	1.452 (2)
N1—C1—C2	129.30 (14)	O1—C10—C9	110.99 (13)
N1—C1—C6	108.61 (13)	C10—C11—C12	113.97 (14)
C2—C1—C6	122.09 (14)	C10—C11—H11	123.0
C3—C2—C1	117.21 (15)	C12—C11—H11	123.0
C3—C2—H2	121.4	N1—C12—C11	128.43 (13)
C1—C2—H2	121.4	N1—C12—C7	108.07 (13)
C2—C3—C4	121.72 (15)	C11—C12—C7	123.50 (14)
C2—C3—H3	119.1	C14—C13—C18	118.94 (15)
C4—C3—H3	119.1	C14—C13—C9	135.24 (15)
C5—C4—C3	120.78 (15)	C18—C13—C9	105.78 (14)
C5—C4—H4	119.6	C13—C14—C15	118.36 (17)
C3—C4—H4	119.6	C13—C14—H14	120.8
C4—C5—C6	118.98 (14)	C15—C14—H14	120.8
C4—C5—H5	120.5	C14—C15—C16	120.92 (18)
C6—C5—H5	120.5	C14—C15—H15	119.5
C5—C6—C1	119.21 (13)	C16—C15—H15	119.5
C5—C6—C7	133.90 (13)	C17—C16—C15	121.69 (16)
C1—C6—C7	106.87 (13)	C17—C16—H16	119.2
C8—C7—C12	120.09 (13)	C15—C16—H16	119.2
C8—C7—C6	133.30 (13)	C16—C17—C18	116.36 (18)
C12—C7—C6	106.59 (12)	C16—C17—H17	121.8
C9—C8—C7	117.52 (12)	C18—C17—H17	121.8
C9—C8—H8	121.2	C17—C18—C13	123.72 (17)
C7—C8—H8	121.2	C17—C18—O1	124.33 (16)
C8—C9—C10	119.61 (13)	C13—C18—O1	111.91 (14)
C8—C9—C13	134.72 (14)	C1—N1—C12	109.77 (12)
C10—C9—C13	105.67 (13)	C1—N1—H1	125.1
C11—C10—O1	123.74 (14)	C12—N1—H1	125.1
C11—C10—C9	125.27 (14)	C10—O1—C18	105.64 (12)
N1—C1—C2—C3	−179.31 (16)	C8—C7—C12—N1	179.51 (13)
C6—C1—C2—C3	−0.1 (2)	C6—C7—C12—N1	−2.04 (16)
C1—C2—C3—C4	0.0 (3)	C8—C7—C12—C11	−1.0 (2)
C2—C3—C4—C5	−0.3 (3)	C6—C7—C12—C11	177.49 (15)
C3—C4—C5—C6	0.6 (2)	C8—C9—C13—C14	3.5 (3)
C4—C5—C6—C1	−0.7 (2)	C10—C9—C13—C14	−176.81 (17)
C4—C5—C6—C7	177.28 (15)	C8—C9—C13—C18	−179.06 (17)
N1—C1—C6—C5	179.83 (13)	C10—C9—C13—C18	0.64 (18)
C2—C1—C6—C5	0.5 (2)	C18—C13—C14—C15	0.1 (2)
N1—C1—C6—C7	1.33 (16)	C9—C13—C14—C15	177.25 (18)
C2—C1—C6—C7	−178.01 (15)	C13—C14—C15—C16	−0.4 (3)
C5—C6—C7—C8	0.4 (3)	C14—C15—C16—C17	0.4 (3)
C1—C6—C7—C8	178.59 (16)	C15—C16—C17—C18	0.0 (3)
C5—C6—C7—C12	−177.74 (17)	C16—C17—C18—C13	−0.3 (3)
C1—C6—C7—C12	0.44 (16)	C16—C17—C18—O1	−177.71 (17)
C12—C7—C8—C9	1.1 (2)	C14—C13—C18—C17	0.3 (3)
C6—C7—C8—C9	−176.87 (15)	C9—C13—C18—C17	−177.67 (16)
C7—C8—C9—C10	0.3 (2)	C14—C13—C18—O1	177.98 (13)
C7—C8—C9—C13	179.98 (16)	C9—C13—C18—O1	0.04 (19)
C8—C9—C10—C11	−2.1 (2)	C2—C1—N1—C12	176.60 (17)
C13—C9—C10—C11	178.14 (16)	C6—C1—N1—C12	−2.68 (17)
C8—C9—C10—O1	178.64 (14)	C11—C12—N1—C1	−176.56 (16)
C13—C9—C10—O1	−1.11 (17)	C7—C12—N1—C1	2.94 (17)
O1—C10—C11—C12	−178.66 (15)	C11—C10—O1—C18	−178.14 (15)
C9—C10—C11—C12	2.2 (2)	C9—C10—O1—C18	1.13 (17)
C10—C11—C12—N1	178.80 (15)	C17—C18—O1—C10	176.98 (17)
C10—C11—C12—C7	−0.6 (2)	C13—C18—O1—C10	−0.71 (18)

Cg2, Cg3 and Cg4 are the centroids of the N1/C1/C6/C7/C12, C1–C6 and C7–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cg4i	0.86	2.91	3.530 (2)	130
C5—H5···Cg2ii	0.93	2.70	3.449 (2)	138
C11—H11···Cg3i	0.93	2.79	3.526 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg2, Cg3 and Cg4 are the centroids of the N1/C1/C6/C7/C12, C1–C6 and C7–C12 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cg4i	0.86	2.91	3.530 (2)	130
C5—H5⋯Cg2ii	0.93	2.70	3.449 (2)	138
C11—H11⋯Cg3i	0.93	2.79	3.526 (2)	137

Symmetry codes: (i) ; (ii) .