9-Allyl-9H-carbazole-3,6-dicarbaldehyde.

In the title mol-ecule, C(17)H(13)NO(2), the allyl group is almost perpendicular to the carbazole mean plane, with a dihedral angle of 89.0 (2)°. In the crystal, nonclassical C-H⋯O hydrogen bonds link the mol-ecules into corrugated sheets parallel to the bc plane. Weak inter-molecular π-π inter-actions are observed between the benzene rings [centroid-centroid distance = 3.874 (4) Å] from neighbouring sheets.

Related literature

For applications of carbazole derivatives, see: Hong et al. (2012 ▶); Samanta et al. (2001 ▶); Koyuncua et al. (2011 ▶); Zhang et al. (2010 ▶). For related structures, see: Wang et al. (2008 ▶); Zhao et al. (2012 ▶).

Experimental

Crystal data

C17H13NO2

M = 263.28

Monoclinic,

a = 8.4062 (8) Å

b = 10.3279 (10) Å

c = 15.2432 (19) Å

β = 94.958 (9)°

V = 1318.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.44 × 0.28 × 0.26 mm

Data collection

Oxford Gemini S Ultra area-detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.963, T max = 0.978

5464 measured reflections

2835 independent reflections

1909 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.118

S = 1.02

2835 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 datablock(s) I, global. DOI: 10.1107/S160053681203190X/cv5316sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203190X/cv5316Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203190X/cv5316Isup3.cml

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

C17H13NO2	Dx = 1.326 Mg m−3
Mr = 263.28	Melting point: 429 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.4062 (8) Å	Cell parameters from 1300 reflections
b = 10.3279 (10) Å	θ = 3.3–29.4°
c = 15.2432 (19) Å	µ = 0.09 mm−1
β = 94.958 (9)°	T = 293 K
V = 1318.4 (2) Å3	Block, light brown
Z = 4	0.44 × 0.28 × 0.26 mm
F(000) = 552

Oxford Gemini S Ultra area-detector diffractometer	2835 independent reflections
Radiation source: fine-focus sealed tube	1909 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 27.0°, θmin = 3.3°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −6→10
Tmin = 0.963, Tmax = 0.978	k = −12→12
5464 measured reflections	l = −19→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0432P)2 + 0.2427P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2835 reflections	Δρmax = 0.16 e Å−3
182 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.047 (4)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
N1	0.59424 (16)	0.67631 (13)	1.01449 (10)	0.0497 (4)
C7	0.69533 (17)	0.55686 (15)	0.90689 (11)	0.0421 (4)
C5	0.84834 (18)	0.39928 (15)	1.01791 (11)	0.0451 (4)
H5	0.8926	0.3478	0.9763	0.054*
C1	0.68710 (19)	0.58033 (16)	1.05593 (12)	0.0461 (4)
C12	0.59952 (19)	0.66450 (16)	0.92455 (12)	0.0461 (4)
C9	0.64340 (19)	0.59883 (17)	0.75251 (12)	0.0483 (4)
C6	0.75183 (18)	0.50343 (15)	0.99146 (11)	0.0422 (4)
C4	0.87835 (19)	0.37238 (17)	1.10679 (12)	0.0483 (4)
C8	0.71472 (19)	0.52431 (16)	0.82040 (11)	0.0455 (4)
H8	0.7756	0.4525	0.8079	0.055*
C2	0.7177 (2)	0.55521 (19)	1.14551 (12)	0.0552 (5)
H2	0.6753	0.6072	1.1875	0.066*
O1	1.00518 (18)	0.22217 (15)	1.20823 (10)	0.0826 (5)
C11	0.5259 (2)	0.73978 (17)	0.85642 (13)	0.0537 (5)
H11	0.4626	0.8105	0.8682	0.064*
O2	0.62394 (17)	0.62669 (15)	0.59663 (10)	0.0806 (5)
C17	0.6687 (2)	0.5651 (2)	0.66156 (13)	0.0587 (5)
H17	0.7245	0.4891	0.6529	0.070*
C3	0.8126 (2)	0.45114 (19)	1.16965 (12)	0.0555 (5)
H3	0.8340	0.4321	1.2291	0.067*
C14	0.5887 (2)	0.89280 (17)	1.08156 (13)	0.0592 (5)
H14	0.5316	0.9572	1.1077	0.071*
C10	0.5500 (2)	0.70602 (17)	0.77173 (13)	0.0546 (5)
H10	0.5031	0.7556	0.7256	0.066*
C13	0.5018 (2)	0.77164 (17)	1.05870 (13)	0.0573 (5)
H13A	0.4682	0.7335	1.1122	0.069*
H13B	0.4064	0.7923	1.0209	0.069*
C16	0.9756 (2)	0.26040 (19)	1.13370 (14)	0.0601 (5)
H16	1.0191	0.2138	1.0893	0.072*
C15	0.7349 (3)	0.9192 (2)	1.06934 (15)	0.0763 (7)
H15A	0.7975	0.8582	1.0435	0.092*
H15B	0.7778	0.9992	1.0864	0.092*

	U11	U22	U33	U12	U13	U23
N1	0.0457 (8)	0.0427 (8)	0.0613 (10)	0.0001 (7)	0.0086 (7)	−0.0127 (7)
C7	0.0380 (8)	0.0360 (8)	0.0528 (11)	−0.0056 (7)	0.0068 (7)	−0.0053 (7)
C5	0.0409 (8)	0.0425 (9)	0.0527 (11)	−0.0054 (8)	0.0089 (7)	−0.0038 (8)
C1	0.0413 (8)	0.0424 (9)	0.0554 (11)	−0.0082 (8)	0.0087 (8)	−0.0086 (8)
C12	0.0397 (8)	0.0384 (9)	0.0605 (12)	−0.0079 (8)	0.0065 (7)	−0.0081 (8)
C9	0.0441 (9)	0.0470 (10)	0.0539 (11)	−0.0096 (9)	0.0047 (8)	0.0030 (8)
C6	0.0382 (8)	0.0398 (9)	0.0490 (10)	−0.0058 (8)	0.0069 (7)	−0.0058 (8)
C4	0.0445 (9)	0.0484 (9)	0.0524 (11)	−0.0071 (8)	0.0059 (8)	0.0036 (8)
C8	0.0432 (8)	0.0403 (9)	0.0541 (11)	−0.0025 (8)	0.0098 (7)	−0.0031 (8)
C2	0.0542 (10)	0.0593 (11)	0.0536 (12)	−0.0077 (10)	0.0141 (8)	−0.0134 (9)
O1	0.0964 (11)	0.0819 (10)	0.0701 (10)	0.0061 (9)	0.0108 (8)	0.0289 (9)
C11	0.0467 (9)	0.0379 (9)	0.0762 (13)	0.0018 (8)	0.0045 (9)	−0.0026 (9)
O2	0.0836 (10)	0.0966 (11)	0.0625 (10)	0.0006 (9)	0.0108 (8)	0.0236 (9)
C17	0.0551 (10)	0.0630 (12)	0.0588 (13)	−0.0077 (10)	0.0090 (9)	0.0089 (10)
C3	0.0556 (10)	0.0632 (12)	0.0481 (11)	−0.0115 (10)	0.0070 (8)	−0.0009 (9)
C14	0.0607 (11)	0.0458 (10)	0.0705 (14)	0.0025 (10)	0.0025 (10)	−0.0154 (9)
C10	0.0494 (10)	0.0454 (10)	0.0681 (13)	−0.0051 (9)	0.0000 (9)	0.0081 (9)
C13	0.0501 (10)	0.0510 (10)	0.0725 (13)	0.0022 (9)	0.0144 (9)	−0.0166 (10)
C16	0.0610 (11)	0.0576 (11)	0.0627 (13)	−0.0049 (10)	0.0105 (9)	0.0114 (10)
C15	0.0719 (14)	0.0600 (13)	0.0958 (18)	−0.0142 (12)	0.0002 (12)	−0.0126 (12)

N1—C1	1.380 (2)	C2—C3	1.370 (3)
N1—C12	1.381 (2)	C2—H2	0.9300
N1—C13	1.455 (2)	O1—C16	1.208 (2)
C7—C8	1.384 (2)	C11—C10	1.369 (2)
C7—C12	1.412 (2)	C11—H11	0.9300
C7—C6	1.444 (2)	O2—C17	1.209 (2)
C5—C4	1.385 (2)	C17—H17	0.9300
C5—C6	1.386 (2)	C3—H3	0.9300
C5—H5	0.9300	C14—C15	1.288 (3)
C1—C2	1.392 (2)	C14—C13	1.475 (2)
C1—C6	1.409 (2)	C14—H14	0.9300
C12—C11	1.398 (2)	C10—H10	0.9300
C9—C8	1.384 (2)	C13—H13A	0.9700
C9—C10	1.403 (2)	C13—H13B	0.9700
C9—C17	1.463 (3)	C16—H16	0.9300
C4—C3	1.406 (3)	C15—H15A	0.9300
C4—C16	1.455 (3)	C15—H15B	0.9300
C8—H8	0.9300
C1—N1—C12	108.99 (13)	C1—C2—H2	121.2
C1—N1—C13	125.26 (16)	C10—C11—C12	117.82 (16)
C12—N1—C13	125.72 (15)	C10—C11—H11	121.1
C8—C7—C12	119.27 (16)	C12—C11—H11	121.1
C8—C7—C6	134.49 (15)	O2—C17—C9	126.2 (2)
C12—C7—C6	106.23 (15)	O2—C17—H17	116.9
C4—C5—C6	119.54 (16)	C9—C17—H17	116.9
C4—C5—H5	120.2	C2—C3—C4	121.67 (17)
C6—C5—H5	120.2	C2—C3—H3	119.2
N1—C1—C2	129.20 (16)	C4—C3—H3	119.2
N1—C1—C6	108.83 (15)	C15—C14—C13	127.18 (19)
C2—C1—C6	121.96 (17)	C15—C14—H14	116.4
N1—C12—C11	129.66 (16)	C13—C14—H14	116.4
N1—C12—C7	109.06 (15)	C11—C10—C9	121.94 (17)
C11—C12—C7	121.27 (17)	C11—C10—H10	119.0
C8—C9—C10	119.79 (17)	C9—C10—H10	119.0
C8—C9—C17	119.17 (17)	N1—C13—C14	114.22 (14)
C10—C9—C17	121.04 (17)	N1—C13—H13A	108.7
C5—C6—C1	119.09 (16)	C14—C13—H13A	108.7
C5—C6—C7	134.05 (15)	N1—C13—H13B	108.7
C1—C6—C7	106.87 (14)	C14—C13—H13B	108.7
C5—C4—C3	120.10 (17)	H13A—C13—H13B	107.6
C5—C4—C16	119.06 (17)	O1—C16—C4	126.1 (2)
C3—C4—C16	120.82 (17)	O1—C16—H16	116.9
C7—C8—C9	119.89 (16)	C4—C16—H16	116.9
C7—C8—H8	120.1	C14—C15—H15A	120.0
C9—C8—H8	120.1	C14—C15—H15B	120.0
C3—C2—C1	117.63 (17)	H15A—C15—H15B	120.0
C3—C2—H2	121.2
C12—N1—C1—C2	179.57 (16)	C6—C5—C4—C16	178.05 (14)
C13—N1—C1—C2	−2.3 (3)	C12—C7—C8—C9	1.4 (2)
C12—N1—C1—C6	−0.97 (17)	C6—C7—C8—C9	−179.34 (16)
C13—N1—C1—C6	177.21 (14)	C10—C9—C8—C7	−0.8 (2)
C1—N1—C12—C11	−179.46 (16)	C17—C9—C8—C7	178.34 (15)
C13—N1—C12—C11	2.4 (3)	N1—C1—C2—C3	178.68 (15)
C1—N1—C12—C7	1.20 (17)	C6—C1—C2—C3	−0.7 (2)
C13—N1—C12—C7	−176.96 (14)	N1—C12—C11—C10	−179.46 (16)
C8—C7—C12—N1	178.47 (13)	C7—C12—C11—C10	−0.2 (2)
C6—C7—C12—N1	−0.95 (17)	C8—C9—C17—O2	−174.17 (17)
C8—C7—C12—C11	−0.9 (2)	C10—C9—C17—O2	5.0 (3)
C6—C7—C12—C11	179.64 (14)	C1—C2—C3—C4	0.5 (3)
C4—C5—C6—C1	0.4 (2)	C5—C4—C3—C2	0.2 (3)
C4—C5—C6—C7	−179.03 (16)	C16—C4—C3—C2	−178.48 (16)
N1—C1—C6—C5	−179.23 (13)	C12—C11—C10—C9	0.8 (2)
C2—C1—C6—C5	0.3 (2)	C8—C9—C10—C11	−0.3 (3)
N1—C1—C6—C7	0.36 (17)	C17—C9—C10—C11	−179.48 (16)
C2—C1—C6—C7	179.87 (14)	C1—N1—C13—C14	91.2 (2)
C8—C7—C6—C5	0.6 (3)	C12—N1—C13—C14	−90.9 (2)
C12—C7—C6—C5	179.86 (16)	C15—C14—C13—N1	−2.6 (3)
C8—C7—C6—C1	−178.93 (16)	C5—C4—C16—O1	−176.38 (18)
C12—C7—C6—C1	0.36 (17)	C3—C4—C16—O1	2.3 (3)
C6—C5—C4—C3	−0.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.58	3.489 (3)	166
C5—H5···O2ii	0.93	2.54	3.332 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.58	3.489 (3)	166
C5—H5⋯O2ii	0.93	2.54	3.332 (2)	143

Symmetry codes: (i) ; (ii) .