9-Ethyl-9H-carbazole-3-carbaldehyde.

The title mol-ecule, C(15)H(13)NO, approximates a planar conformation except for the alkyl chain (ethyl group) bonded to the N atom with a maximum deviation from the least-squares plane through the 15 planar atoms of 0.120 (2) Å for the O atom. The distance of the formyl O atom from the plane of the carbazole ring is 0.227 (2) Å. The N-C bond lengths in the central ring are significantly different, reflecting the electron-withdrawing properties of the aldehyde group. As a consequence, charge transfer may occur from the carbazole N atom to the substituted benzene ring.

Related literature

For the properties of carbazole derivatives, see: van Dijken et al. (2004 ▶); Li et al. (2005 ▶). For the X-ray structure of 9-ethyl-3,6-diformyl-9H-carbazole, see: Wang et al. (2008 ▶) and of 9-ethyl-9H-carbazole, see: Kimura et al. (1985 ▶).

Experimental

Crystal data

C15H13NO

M = 223.26

Monoclinic,

a = 10.6523 (10) Å

b = 8.2312 (6) Å

c = 13.8005 (12) Å

β = 104.387 (1)°

V = 1172.10 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.50 × 0.44 × 0.43 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.961, T max = 0.967

5763 measured reflections

2065 independent reflections

1313 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.116

S = 1.05

2065 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.11 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025183/bh2297sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025183/bh2297Isup2.hkl

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

C15H13NO	F(000) = 472
Mr = 223.26	Dx = 1.265 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1960 reflections
a = 10.6523 (10) Å	θ = 2.8–25.2°
b = 8.2312 (6) Å	µ = 0.08 mm−1
c = 13.8005 (12) Å	T = 298 K
β = 104.387 (1)°	Block, colorless
V = 1172.10 (17) Å3	0.50 × 0.44 × 0.43 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2065 independent reflections
Radiation source: fine-focus sealed tube	1313 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.961, Tmax = 0.967	k = −9→5
5763 measured reflections	l = −16→16

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0369P)2 + 0.3721P] where P = (Fo2 + 2Fc2)/3
2065 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.11 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
N1	0.23808 (16)	0.0604 (2)	0.36043 (12)	0.0579 (5)
O1	0.83067 (17)	0.1354 (3)	0.36513 (14)	0.0966 (6)
C1	0.3591 (2)	0.0376 (3)	0.34470 (15)	0.0518 (5)
C2	0.3972 (2)	−0.0683 (3)	0.27949 (16)	0.0631 (6)
H2	0.3382	−0.1383	0.2390	0.076*
C3	0.5250 (2)	−0.0665 (3)	0.27648 (16)	0.0626 (6)
H3	0.5528	−0.1382	0.2340	0.075*
C4	0.6142 (2)	0.0397 (3)	0.33530 (15)	0.0545 (6)
C5	0.5753 (2)	0.1450 (3)	0.40056 (14)	0.0529 (5)
H5	0.6347	0.2157	0.4401	0.063*
C6	0.44792 (19)	0.1444 (2)	0.40663 (13)	0.0466 (5)
C7	0.37450 (19)	0.2342 (2)	0.46404 (14)	0.0489 (5)
C8	0.4063 (2)	0.3526 (3)	0.53694 (16)	0.0639 (6)
H8	0.4914	0.3886	0.5592	0.077*
C9	0.3104 (3)	0.4162 (3)	0.57591 (18)	0.0766 (7)
H9	0.3304	0.4973	0.6242	0.092*
C10	0.1842 (3)	0.3611 (3)	0.54428 (19)	0.0773 (7)
H10	0.1211	0.4063	0.5720	0.093*
C11	0.1490 (2)	0.2417 (3)	0.47318 (17)	0.0666 (7)
H11	0.0640	0.2049	0.4524	0.080*
C12	0.2467 (2)	0.1786 (3)	0.43386 (15)	0.0531 (5)
C13	0.7479 (2)	0.0386 (3)	0.32700 (18)	0.0709 (7)
H13	0.7716	−0.0439	0.2890	0.085*
C14	0.1223 (2)	−0.0304 (3)	0.31232 (18)	0.0747 (7)
H14A	0.1251	−0.0561	0.2443	0.090*
H14B	0.0467	0.0368	0.3092	0.090*
C15	0.1098 (3)	−0.1842 (4)	0.3666 (2)	0.1012 (10)
H15A	0.1832	−0.2527	0.3679	0.152*
H15B	0.0318	−0.2395	0.3329	0.152*
H15C	0.1065	−0.1593	0.4339	0.152*

	U11	U22	U33	U12	U13	U23
N1	0.0484 (11)	0.0677 (12)	0.0556 (11)	−0.0109 (9)	0.0089 (8)	−0.0058 (10)
O1	0.0640 (12)	0.1300 (18)	0.1015 (14)	−0.0201 (12)	0.0310 (10)	0.0030 (13)
C1	0.0529 (13)	0.0550 (13)	0.0474 (12)	−0.0049 (10)	0.0122 (10)	0.0044 (10)
C2	0.0631 (15)	0.0672 (16)	0.0590 (14)	−0.0122 (12)	0.0152 (11)	−0.0083 (12)
C3	0.0731 (17)	0.0609 (15)	0.0577 (14)	0.0011 (12)	0.0239 (12)	−0.0005 (12)
C4	0.0584 (14)	0.0573 (14)	0.0494 (12)	−0.0012 (11)	0.0169 (10)	0.0115 (11)
C5	0.0529 (13)	0.0560 (13)	0.0480 (12)	−0.0121 (10)	0.0093 (10)	0.0098 (11)
C6	0.0495 (12)	0.0483 (12)	0.0411 (11)	−0.0056 (10)	0.0093 (9)	0.0083 (10)
C7	0.0567 (13)	0.0473 (12)	0.0427 (11)	−0.0095 (10)	0.0123 (9)	0.0086 (10)
C8	0.0803 (17)	0.0608 (15)	0.0553 (13)	−0.0202 (13)	0.0257 (12)	−0.0002 (12)
C9	0.109 (2)	0.0605 (16)	0.0702 (16)	−0.0180 (15)	0.0410 (15)	−0.0074 (13)
C10	0.095 (2)	0.0729 (17)	0.0764 (17)	0.0029 (16)	0.0449 (15)	0.0022 (15)
C11	0.0623 (15)	0.0761 (17)	0.0652 (14)	−0.0018 (13)	0.0228 (12)	0.0092 (14)
C12	0.0581 (14)	0.0559 (13)	0.0454 (11)	−0.0020 (11)	0.0129 (10)	0.0079 (11)
C13	0.0654 (17)	0.0861 (19)	0.0677 (16)	0.0026 (14)	0.0289 (13)	0.0157 (14)
C14	0.0548 (15)	0.097 (2)	0.0704 (15)	−0.0197 (13)	0.0114 (12)	−0.0166 (15)
C15	0.108 (2)	0.108 (2)	0.092 (2)	−0.0571 (19)	0.0328 (17)	−0.0225 (19)

N1—C1	1.372 (3)	C7—C12	1.398 (3)
N1—C12	1.391 (3)	C8—C9	1.371 (3)
N1—C14	1.453 (3)	C8—H8	0.9300
O1—C13	1.208 (3)	C9—C10	1.382 (3)
C1—C2	1.384 (3)	C9—H9	0.9300
C1—C6	1.413 (3)	C10—C11	1.374 (3)
C2—C3	1.372 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.388 (3)
C3—C4	1.394 (3)	C11—H11	0.9300
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.385 (3)	C14—C15	1.494 (4)
C4—C13	1.457 (3)	C14—H14A	0.9700
C5—C6	1.380 (3)	C14—H14B	0.9700
C5—H5	0.9300	C15—H15A	0.9600
C6—C7	1.447 (3)	C15—H15B	0.9600
C7—C8	1.381 (3)	C15—H15C	0.9600
C1—N1—C12	108.45 (16)	C8—C9—C10	120.8 (2)
C1—N1—C14	125.50 (19)	C8—C9—H9	119.6
C12—N1—C14	125.96 (19)	C10—C9—H9	119.6
N1—C1—C2	128.9 (2)	C11—C10—C9	122.1 (2)
N1—C1—C6	109.47 (18)	C11—C10—H10	118.9
C2—C1—C6	121.60 (19)	C9—C10—H10	118.9
C3—C2—C1	117.8 (2)	C10—C11—C12	116.7 (2)
C3—C2—H2	121.1	C10—C11—H11	121.7
C1—C2—H2	121.1	C12—C11—H11	121.7
C2—C3—C4	121.8 (2)	C11—C12—N1	128.8 (2)
C2—C3—H3	119.1	C11—C12—C7	122.0 (2)
C4—C3—H3	119.1	N1—C12—C7	109.22 (18)
C5—C4—C3	120.0 (2)	O1—C13—C4	125.7 (3)
C5—C4—C13	120.7 (2)	O1—C13—H13	117.1
C3—C4—C13	119.2 (2)	C4—C13—H13	117.1
C6—C5—C4	119.61 (19)	N1—C14—C15	112.2 (2)
C6—C5—H5	120.2	N1—C14—H14A	109.2
C4—C5—H5	120.2	C15—C14—H14A	109.2
C5—C6—C1	119.12 (19)	N1—C14—H14B	109.2
C5—C6—C7	134.79 (19)	C15—C14—H14B	109.2
C1—C6—C7	106.09 (17)	H14A—C14—H14B	107.9
C8—C7—C12	119.5 (2)	C14—C15—H15A	109.5
C8—C7—C6	133.74 (19)	C14—C15—H15B	109.5
C12—C7—C6	106.76 (18)	H15A—C15—H15B	109.5
C9—C8—C7	118.9 (2)	C14—C15—H15C	109.5
C9—C8—H8	120.6	H15A—C15—H15C	109.5
C7—C8—H8	120.6	H15B—C15—H15C	109.5
C12—N1—C1—C2	179.4 (2)	C1—C6—C7—C12	−0.3 (2)
C14—N1—C1—C2	2.6 (3)	C12—C7—C8—C9	−1.9 (3)
C12—N1—C1—C6	−1.4 (2)	C6—C7—C8—C9	178.8 (2)
C14—N1—C1—C6	−178.23 (19)	C7—C8—C9—C10	1.1 (3)
N1—C1—C2—C3	179.0 (2)	C8—C9—C10—C11	0.0 (4)
C6—C1—C2—C3	−0.1 (3)	C9—C10—C11—C12	−0.2 (3)
C1—C2—C3—C4	−1.2 (3)	C10—C11—C12—N1	−178.6 (2)
C2—C3—C4—C5	1.4 (3)	C10—C11—C12—C7	−0.6 (3)
C2—C3—C4—C13	−178.5 (2)	C1—N1—C12—C11	179.4 (2)
C3—C4—C5—C6	−0.2 (3)	C14—N1—C12—C11	−3.8 (3)
C13—C4—C5—C6	179.62 (18)	C1—N1—C12—C7	1.2 (2)
C4—C5—C6—C1	−1.0 (3)	C14—N1—C12—C7	178.0 (2)
C4—C5—C6—C7	−179.8 (2)	C8—C7—C12—C11	1.7 (3)
N1—C1—C6—C5	−178.10 (17)	C6—C7—C12—C11	−178.88 (19)
C2—C1—C6—C5	1.2 (3)	C8—C7—C12—N1	−179.94 (17)
N1—C1—C6—C7	1.1 (2)	C6—C7—C12—N1	−0.5 (2)
C2—C1—C6—C7	−179.68 (19)	C5—C4—C13—O1	−8.4 (3)
C5—C6—C7—C8	−2.0 (4)	C3—C4—C13—O1	171.5 (2)
C1—C6—C7—C8	179.0 (2)	C1—N1—C14—C15	86.1 (3)
C5—C6—C7—C12	178.6 (2)	C12—N1—C14—C15	−90.2 (3)