(E)-2-[(Furan-2-yl)methyl-idene]-7-methyl-2,3,4,9-tetra-hydro-1H-carbazol-1-one.

In the title mol-ecule, C(18)H(15)NO(2), the atoms in the carbazole unit deviate from planarity [maximum deviation from mean plane = 0.1317 (12) Å]. The pyrrole ring makes dihedral angles of 1.01 (8) and 18.56 (10)° with the benzene and furan rings, respectively. The cyclo-hexene ring adopts a half-chair conformation. In the crystal, pairs of N-H⋯O hydrogen bonds form an R(2) (2)(10) ring. Mol-ecules are further linked by C-H⋯O and C-H⋯π inter-actions, forming a three-dimensional network.

Related literature

For a related structure and the synthesis and applications of carbazole derivatives, see: Archana et al. (2010 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H15NO2

M = 277.31

Triclinic,

a = 6.3925 (3) Å

b = 7.9880 (4) Å

c = 13.8629 (8) Å

α = 83.151 (5)°

β = 81.649 (4)°

γ = 78.921 (4)°

V = 684.28 (6) Å3

Z = 2

Cu Kα radiation

μ = 0.70 mm−1

T = 123 K

0.34 × 0.26 × 0.12 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.816, T max = 1.000

4371 measured reflections

2724 independent reflections

2382 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.132

S = 1.05

2724 reflections

199 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812051203/tk5183sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051203/tk5183Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051203/tk5183Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051203/tk5183Isup4.cml

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

C18H15NO2	Z = 2
Mr = 277.31	F(000) = 292
Triclinic, P1	Dx = 1.346 Mg m−3
Hall symbol: -P 1	Melting point: 402 K
a = 6.3925 (3) Å	Cu Kα radiation, λ = 1.54184 Å
b = 7.9880 (4) Å	Cell parameters from 2052 reflections
c = 13.8629 (8) Å	θ = 5.7–75.5°
α = 83.151 (5)°	µ = 0.70 mm−1
β = 81.649 (4)°	T = 123 K
γ = 78.921 (4)°	Prism, colourless
V = 684.28 (6) Å3	0.34 × 0.26 × 0.12 mm

Agilent Xcalibur Ruby Gemini diffractometer	2724 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2382 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 10.5081 pixels mm-1	θmax = 75.7°, θmin = 5.7°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −8→9
Tmin = 0.816, Tmax = 1.000	l = −17→17
4371 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0769P)2 + 0.1562P] where P = (Fo2 + 2Fc2)/3
2724 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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
O1	0.82745 (16)	0.54561 (14)	−0.10721 (8)	0.0321 (3)
O11	0.4389 (2)	0.62235 (18)	−0.38788 (8)	0.0462 (4)
N9	0.77421 (19)	0.66480 (16)	0.08384 (9)	0.0272 (3)
C1	0.6548 (2)	0.63419 (18)	−0.07581 (10)	0.0256 (4)
C2	0.4695 (2)	0.68389 (18)	−0.13316 (10)	0.0259 (4)
C3	0.2549 (2)	0.77564 (19)	−0.08760 (11)	0.0296 (4)
C4	0.2491 (2)	0.86429 (18)	0.00542 (11)	0.0275 (4)
C4A	0.4362 (2)	0.79645 (18)	0.05978 (10)	0.0258 (4)
C4B	0.4742 (2)	0.82727 (18)	0.15417 (10)	0.0279 (4)
C5	0.3503 (3)	0.9176 (2)	0.23067 (12)	0.0346 (5)
C6	0.4421 (3)	0.9234 (2)	0.31372 (12)	0.0404 (5)
C7	0.6555 (3)	0.8434 (2)	0.32410 (12)	0.0375 (5)
C8	0.7788 (3)	0.7521 (2)	0.25079 (11)	0.0328 (5)
C8A	0.6863 (2)	0.74409 (18)	0.16619 (10)	0.0285 (4)
C9A	0.6217 (2)	0.69588 (17)	0.01966 (10)	0.0252 (4)
C10	0.5039 (2)	0.63565 (19)	−0.22508 (11)	0.0298 (4)
C12	0.2715 (3)	0.6422 (3)	−0.44181 (13)	0.0492 (6)
C13	0.0838 (3)	0.6875 (2)	−0.38630 (13)	0.0433 (5)
C14	0.1333 (3)	0.6999 (2)	−0.29094 (12)	0.0366 (5)
C15	0.3511 (3)	0.6590 (2)	−0.29413 (11)	0.0317 (4)
C17	0.7481 (3)	0.8590 (3)	0.41581 (13)	0.0476 (6)
H3A	0.19484	0.86329	−0.13780	0.0355*
H3B	0.15695	0.69133	−0.07227	0.0355*
H4A	0.11559	0.85019	0.04927	0.0329*
H4B	0.24433	0.98848	−0.01290	0.0329*
H5	0.20662	0.97310	0.22495	0.0415*
H6	0.35921	0.98317	0.36572	0.0485*
H8	0.92199	0.69650	0.25754	0.0394*
H9	0.900 (3)	0.600 (2)	0.0795 (13)	0.033 (5)*
H10	0.644 (3)	0.575 (2)	−0.2485 (14)	0.038 (5)*
H12	0.28626	0.62615	−0.50943	0.0590*
H13	−0.05517	0.70746	−0.40667	0.0520*
H14	0.03333	0.73078	−0.23547	0.0439*
H17A	0.89806	0.80012	0.41094	0.0714*
H17B	0.74130	0.98028	0.42362	0.0714*
H17C	0.66510	0.80661	0.47255	0.0714*

	U11	U22	U33	U12	U13	U23
O1	0.0224 (5)	0.0448 (6)	0.0290 (5)	−0.0035 (4)	−0.0033 (4)	−0.0073 (4)
O11	0.0401 (7)	0.0717 (9)	0.0272 (6)	−0.0045 (6)	−0.0073 (5)	−0.0117 (5)
N9	0.0233 (6)	0.0337 (6)	0.0261 (6)	−0.0056 (5)	−0.0062 (5)	−0.0041 (5)
C1	0.0221 (7)	0.0301 (7)	0.0259 (7)	−0.0081 (5)	−0.0029 (5)	−0.0020 (5)
C2	0.0240 (7)	0.0291 (7)	0.0260 (7)	−0.0080 (5)	−0.0046 (5)	−0.0007 (5)
C3	0.0254 (7)	0.0345 (7)	0.0297 (7)	−0.0035 (5)	−0.0080 (5)	−0.0040 (6)
C4	0.0235 (6)	0.0297 (7)	0.0294 (7)	−0.0044 (5)	−0.0042 (5)	−0.0033 (5)
C4A	0.0255 (7)	0.0268 (7)	0.0260 (7)	−0.0080 (5)	−0.0029 (5)	−0.0017 (5)
C4B	0.0297 (7)	0.0289 (7)	0.0265 (7)	−0.0079 (5)	−0.0045 (5)	−0.0028 (5)
C5	0.0368 (8)	0.0348 (8)	0.0312 (8)	−0.0035 (6)	−0.0030 (6)	−0.0056 (6)
C6	0.0522 (10)	0.0408 (9)	0.0282 (8)	−0.0065 (7)	−0.0021 (7)	−0.0092 (6)
C7	0.0505 (10)	0.0384 (8)	0.0271 (8)	−0.0136 (7)	−0.0087 (7)	−0.0033 (6)
C8	0.0373 (8)	0.0356 (8)	0.0281 (8)	−0.0094 (6)	−0.0102 (6)	−0.0014 (6)
C8A	0.0317 (7)	0.0298 (7)	0.0260 (7)	−0.0097 (6)	−0.0044 (5)	−0.0025 (5)
C9A	0.0225 (6)	0.0286 (7)	0.0261 (7)	−0.0076 (5)	−0.0046 (5)	−0.0018 (5)
C10	0.0278 (7)	0.0349 (7)	0.0276 (7)	−0.0079 (6)	−0.0043 (5)	−0.0022 (6)
C12	0.0519 (11)	0.0675 (12)	0.0307 (8)	−0.0055 (9)	−0.0171 (8)	−0.0089 (8)
C13	0.0437 (9)	0.0556 (10)	0.0337 (9)	−0.0087 (8)	−0.0169 (7)	−0.0019 (7)
C14	0.0360 (8)	0.0463 (9)	0.0289 (8)	−0.0081 (7)	−0.0099 (6)	−0.0014 (6)
C15	0.0364 (8)	0.0362 (8)	0.0236 (7)	−0.0088 (6)	−0.0047 (6)	−0.0022 (6)
C17	0.0567 (11)	0.0582 (11)	0.0317 (9)	−0.0111 (9)	−0.0140 (8)	−0.0078 (8)

O1—C1	1.2418 (17)	C8—C8A	1.401 (2)
O11—C12	1.367 (2)	C10—C15	1.437 (2)
O11—C15	1.3804 (19)	C12—C13	1.340 (3)
N9—C8A	1.3673 (19)	C13—C14	1.422 (2)
N9—C9A	1.3820 (18)	C14—C15	1.363 (3)
N9—H9	0.867 (18)	C3—H3A	0.9900
C1—C2	1.4867 (19)	C3—H3B	0.9900
C1—C9A	1.4399 (19)	C4—H4A	0.9900
C2—C3	1.513 (2)	C4—H4B	0.9900
C2—C10	1.351 (2)	C5—H5	0.9500
C3—C4	1.536 (2)	C6—H6	0.9500
C4—C4A	1.4857 (19)	C8—H8	0.9500
C4A—C9A	1.3819 (19)	C10—H10	0.964 (19)
C4A—C4B	1.4227 (19)	C12—H12	0.9500
C4B—C5	1.411 (2)	C13—H13	0.9500
C4B—C8A	1.4144 (19)	C14—H14	0.9500
C5—C6	1.375 (2)	C17—H17A	0.9800
C6—C7	1.411 (3)	C17—H17B	0.9800
C7—C17	1.506 (3)	C17—H17C	0.9800
C7—C8	1.382 (2)
C12—O11—C15	106.77 (14)	C10—C15—C14	136.41 (15)
C8A—N9—C9A	107.83 (12)	O11—C15—C10	114.65 (15)
C9A—N9—H9	129.7 (12)	O11—C15—C14	108.81 (14)
C8A—N9—H9	122.2 (12)	C2—C3—H3A	108.00
O1—C1—C9A	121.59 (12)	C2—C3—H3B	108.00
O1—C1—C2	122.91 (13)	C4—C3—H3A	108.00
C2—C1—C9A	115.50 (12)	C4—C3—H3B	108.00
C3—C2—C10	123.32 (12)	H3A—C3—H3B	107.00
C1—C2—C3	120.81 (12)	C3—C4—H4A	109.00
C1—C2—C10	115.81 (12)	C3—C4—H4B	109.00
C2—C3—C4	118.19 (11)	C4A—C4—H4A	109.00
C3—C4—C4A	113.51 (12)	C4A—C4—H4B	109.00
C4B—C4A—C9A	106.39 (12)	H4A—C4—H4B	108.00
C4—C4A—C4B	130.26 (13)	C4B—C5—H5	121.00
C4—C4A—C9A	123.17 (13)	C6—C5—H5	121.00
C5—C4B—C8A	118.99 (13)	C5—C6—H6	119.00
C4A—C4B—C5	134.20 (14)	C7—C6—H6	119.00
C4A—C4B—C8A	106.80 (12)	C7—C8—H8	121.00
C4B—C5—C6	118.52 (16)	C8A—C8—H8	121.00
C5—C6—C7	122.07 (16)	C2—C10—H10	118.6 (12)
C6—C7—C17	119.33 (15)	C15—C10—H10	113.9 (11)
C6—C7—C8	120.43 (16)	O11—C12—H12	125.00
C8—C7—C17	120.25 (17)	C13—C12—H12	125.00
C7—C8—C8A	117.99 (16)	C12—C13—H13	127.00
N9—C8A—C8	129.24 (13)	C14—C13—H13	127.00
C4B—C8A—C8	121.97 (13)	C13—C14—H14	126.00
N9—C8A—C4B	108.78 (12)	C15—C14—H14	126.00
C1—C9A—C4A	125.39 (12)	C7—C17—H17A	109.00
N9—C9A—C1	124.41 (12)	C7—C17—H17B	109.00
N9—C9A—C4A	110.20 (12)	C7—C17—H17C	109.00
C2—C10—C15	127.43 (13)	H17A—C17—H17B	110.00
O11—C12—C13	110.73 (16)	H17A—C17—H17C	109.00
C12—C13—C14	106.59 (17)	H17B—C17—H17C	109.00
C13—C14—C15	107.09 (15)
C15—O11—C12—C13	−0.7 (2)	C9A—C4A—C4B—C8A	0.82 (16)
C12—O11—C15—C10	176.78 (15)	C4—C4A—C9A—N9	174.68 (13)
C12—O11—C15—C14	0.2 (2)	C4—C4A—C9A—C1	−4.3 (2)
C9A—N9—C8A—C4B	−0.07 (16)	C4B—C4A—C9A—N9	−0.89 (16)
C9A—N9—C8A—C8	−178.77 (15)	C4B—C4A—C9A—C1	−179.83 (13)
C8A—N9—C9A—C1	179.56 (13)	C4A—C4B—C5—C6	−178.90 (16)
C8A—N9—C9A—C4A	0.61 (16)	C8A—C4B—C5—C6	1.0 (2)
O1—C1—C2—C3	173.38 (13)	C4A—C4B—C8A—N9	−0.47 (16)
O1—C1—C2—C10	−4.0 (2)	C4A—C4B—C8A—C8	178.34 (14)
C9A—C1—C2—C3	−6.67 (19)	C5—C4B—C8A—N9	179.64 (13)
C9A—C1—C2—C10	176.00 (13)	C5—C4B—C8A—C8	−1.6 (2)
O1—C1—C9A—N9	0.4 (2)	C4B—C5—C6—C7	0.5 (2)
O1—C1—C9A—C4A	179.22 (14)	C5—C6—C7—C8	−1.5 (3)
C2—C1—C9A—N9	−179.53 (13)	C5—C6—C7—C17	178.27 (17)
C2—C1—C9A—C4A	−0.7 (2)	C6—C7—C8—C8A	0.9 (2)
C1—C2—C3—C4	18.4 (2)	C17—C7—C8—C8A	−178.87 (16)
C10—C2—C3—C4	−164.48 (14)	C7—C8—C8A—N9	179.15 (15)
C1—C2—C10—C15	176.62 (14)	C7—C8—C8A—C4B	0.6 (2)
C3—C2—C10—C15	−0.6 (2)	C2—C10—C15—O11	169.91 (15)
C2—C3—C4—C4A	−21.58 (18)	C2—C10—C15—C14	−14.9 (3)
C3—C4—C4A—C4B	−170.30 (14)	O11—C12—C13—C14	0.8 (2)
C3—C4—C4A—C9A	15.28 (19)	C12—C13—C14—C15	−0.6 (2)
C4—C4A—C4B—C5	5.6 (3)	C13—C14—C15—O11	0.24 (18)
C4—C4A—C4B—C8A	−174.32 (14)	C13—C14—C15—C10	−175.19 (18)
C9A—C4A—C4B—C5	−179.32 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···O1i	0.867 (18)	1.961 (18)	2.8069 (17)	164.9 (17)
C14—H14···O1ii	0.95	2.55	3.250 (2)	130
C4—H4B···Cg2iii	0.99	2.60	3.5176 (16)	154
C17—H17B···Cg1iii	0.98	2.89	3.807 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg1 are the centroids of the pyrrole (N9/C9A/C4A/C4B/C8A) and furan (O11/C12–C15)rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9⋯O1i	0.867 (18)	1.961 (18)	2.8069 (17)	164.9 (17)
C14—H14⋯O1ii	0.95	2.55	3.250 (2)	130
C4—H4B⋯Cg2iii	0.99	2.60	3.5176 (16)	154
C17—H17B⋯Cg1iii	0.98	2.89	3.807 (2)	156

Symmetry codes: (i) ; (ii) ; (iii) .