Indizoline.

THE TITLE COMPOUND [SYSTEMATIC NAME: 1-meth-oxy-2-(3-methyl-but-2-en-yl)-9H-carbazole-3-carbaldehyde], C(19)H(19)NO(2), is a natural carbazole which was isolated from the twigs of Clausena lansium. The carbazole ring system is essentially planar with a mean deviation of 0.0068 (10) Å. The aldehyde substituent is approximately co-planar with the attached benzene ring with a torsion angle of -8.58 (14)°, whereas the meth-oxy group is rotated out of the benzene plane with a torsion angle of -82.17 (11)°. The dihedral angle between the mean planes of the 3-methyl-2-butenyl group and the carbazole ring is 88.06 (5)°. An inter-molecular N-H⋯O inter-action connects the mol-ecules into a chain along the a axis. The crystal is further consolidated by a C-H⋯O hydrogen bond and two π-π inter-actions with centroid-centroid distances of 3.6592 (6) and 3.7440 (6) Å.

Related literature

For bond-length data, see Allen et al. (1987 ▶). For background to carbazoles and their biological activity, see: Adebajo et al. (2009 ▶); Ito et al. (1998 ▶); Kumar et al. (1995 ▶); Lin (1989 ▶); Ng et al. (2003 ▶); Yang et al. (1988 ▶). For a related structure, see: Fun et al. (2007 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C19H19NO2

M = 293.35

Triclinic,

a = 9.0467 (1) Å

b = 9.3257 (1) Å

c = 10.6927 (1) Å

α = 65.717 (1)°

β = 86.994 (1)°

γ = 68.323 (1)°

V = 758.86 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.53 × 0.27 × 0.22 mm

Data collection

Bruker APEXII CCD area detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.957, T max = 0.982

20515 measured reflections

4410 independent reflections

3887 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.124

S = 1.05

4410 reflections

206 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036915/is2459sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036915/is2459Isup2.hkl

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

C19H19NO2	Z = 2
Mr = 293.35	F(000) = 312
Triclinic, P1	Dx = 1.284 Mg m−3
Hall symbol: -P 1	Melting point = 344–345 K
a = 9.0467 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3257 (1) Å	Cell parameters from 4410 reflections
c = 10.6927 (1) Å	θ = 2.1–30.0°
α = 65.717 (1)°	µ = 0.08 mm−1
β = 86.994 (1)°	T = 100 K
γ = 68.323 (1)°	Block, yellow
V = 758.86 (2) Å3	0.53 × 0.27 × 0.22 mm

Bruker APEXII CCD area detector diffractometer	4410 independent reflections
Radiation source: sealed tube	3887 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 30.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.957, Tmax = 0.982	k = −13→13
20515 measured reflections	l = −15→15

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0684P)2 + 0.2509P] where P = (Fo2 + 2Fc2)/3
4410 reflections	(Δ/σ)max = 0.001
206 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.26909 (8)	0.78512 (9)	0.28630 (7)	0.01884 (16)
O2	0.90034 (9)	0.78623 (10)	0.07678 (8)	0.02297 (17)
N1	0.23115 (10)	0.73264 (11)	0.03746 (9)	0.01646 (17)
C1	0.26191 (11)	0.70558 (11)	−0.08151 (10)	0.01576 (18)
C2	0.16804 (12)	0.67357 (12)	−0.15826 (11)	0.0196 (2)
H2A	0.0692	0.6690	−0.1336	0.024*
C3	0.22843 (13)	0.64886 (13)	−0.27314 (11)	0.0212 (2)
H3A	0.1685	0.6274	−0.3264	0.025*
C4	0.37714 (13)	0.65536 (13)	−0.31088 (10)	0.0204 (2)
H4A	0.4140	0.6386	−0.3886	0.024*
C5	0.47039 (12)	0.68656 (12)	−0.23362 (10)	0.01765 (19)
H5A	0.5694	0.6902	−0.2585	0.021*
C6	0.41224 (11)	0.71237 (11)	−0.11773 (9)	0.01449 (17)
C7	0.47446 (11)	0.74608 (11)	−0.01497 (9)	0.01365 (17)
C8	0.61476 (11)	0.76411 (11)	0.00817 (9)	0.01443 (17)
H8A	0.6938	0.7538	−0.0505	0.017*
C9	0.63649 (11)	0.79781 (11)	0.11998 (9)	0.01434 (17)
C10	0.51798 (11)	0.81249 (11)	0.21241 (9)	0.01415 (17)
C11	0.38006 (11)	0.78850 (11)	0.19182 (9)	0.01450 (18)
C12	0.35762 (11)	0.75789 (11)	0.07777 (9)	0.01417 (17)
C13	0.78581 (11)	0.81675 (12)	0.14115 (10)	0.01751 (19)
H13A	0.7940	0.8543	0.2077	0.021*
C14	0.54154 (12)	0.84670 (12)	0.33525 (10)	0.01731 (18)
H14A	0.5751	0.9421	0.3046	0.021*
H14B	0.4400	0.8784	0.3718	0.021*
C15	0.66415 (12)	0.69530 (12)	0.44873 (10)	0.01723 (19)
H15A	0.6619	0.5895	0.4679	0.021*
C16	0.77577 (12)	0.69655 (12)	0.52484 (10)	0.01787 (19)
C17	0.79953 (15)	0.85421 (14)	0.50890 (13)	0.0288 (2)
H17A	0.7349	0.9490	0.4273	0.043*
H17B	0.9103	0.8374	0.5010	0.043*
H17C	0.7686	0.8769	0.5882	0.043*
C18	0.88710 (13)	0.53395 (13)	0.63786 (11)	0.0229 (2)
H18A	0.8557	0.4422	0.6485	0.034*
H18B	0.8819	0.5463	0.7230	0.034*
H18C	0.9947	0.5097	0.6141	0.034*
C19	0.13064 (13)	0.94117 (15)	0.24419 (12)	0.0251 (2)
H19A	0.0625	0.9333	0.3166	0.038*
H19B	0.0730	0.9607	0.1621	0.038*
H19C	0.1639	1.0339	0.2256	0.038*
H1N1	0.145 (2)	0.7418 (19)	0.0698 (16)	0.029 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0144 (3)	0.0228 (3)	0.0189 (3)	−0.0072 (3)	0.0064 (3)	−0.0089 (3)
O2	0.0127 (3)	0.0318 (4)	0.0239 (4)	−0.0103 (3)	0.0028 (3)	−0.0097 (3)
N1	0.0107 (4)	0.0217 (4)	0.0199 (4)	−0.0077 (3)	0.0032 (3)	−0.0102 (3)
C1	0.0129 (4)	0.0159 (4)	0.0182 (4)	−0.0051 (3)	0.0004 (3)	−0.0070 (3)
C2	0.0148 (4)	0.0203 (4)	0.0247 (5)	−0.0065 (3)	−0.0012 (3)	−0.0103 (4)
C3	0.0208 (5)	0.0206 (4)	0.0226 (5)	−0.0067 (4)	−0.0033 (4)	−0.0100 (4)
C4	0.0237 (5)	0.0197 (4)	0.0182 (4)	−0.0073 (4)	0.0003 (4)	−0.0090 (3)
C5	0.0175 (4)	0.0177 (4)	0.0176 (4)	−0.0064 (3)	0.0026 (3)	−0.0077 (3)
C6	0.0123 (4)	0.0139 (4)	0.0161 (4)	−0.0043 (3)	0.0005 (3)	−0.0056 (3)
C7	0.0108 (4)	0.0138 (4)	0.0153 (4)	−0.0045 (3)	0.0014 (3)	−0.0052 (3)
C8	0.0105 (4)	0.0158 (4)	0.0160 (4)	−0.0050 (3)	0.0027 (3)	−0.0060 (3)
C9	0.0107 (4)	0.0147 (4)	0.0163 (4)	−0.0051 (3)	0.0006 (3)	−0.0050 (3)
C10	0.0120 (4)	0.0142 (4)	0.0153 (4)	−0.0047 (3)	0.0007 (3)	−0.0055 (3)
C11	0.0112 (4)	0.0160 (4)	0.0160 (4)	−0.0054 (3)	0.0034 (3)	−0.0064 (3)
C12	0.0102 (4)	0.0150 (4)	0.0166 (4)	−0.0048 (3)	0.0011 (3)	−0.0060 (3)
C13	0.0133 (4)	0.0201 (4)	0.0178 (4)	−0.0077 (3)	−0.0002 (3)	−0.0052 (3)
C14	0.0152 (4)	0.0192 (4)	0.0179 (4)	−0.0052 (3)	0.0007 (3)	−0.0093 (3)
C15	0.0171 (4)	0.0177 (4)	0.0166 (4)	−0.0071 (3)	0.0021 (3)	−0.0066 (3)
C16	0.0156 (4)	0.0200 (4)	0.0173 (4)	−0.0065 (3)	0.0017 (3)	−0.0075 (3)
C17	0.0303 (6)	0.0248 (5)	0.0321 (6)	−0.0115 (4)	−0.0063 (4)	−0.0109 (4)
C18	0.0216 (5)	0.0231 (5)	0.0200 (4)	−0.0078 (4)	−0.0023 (4)	−0.0053 (4)
C19	0.0161 (5)	0.0297 (5)	0.0280 (5)	−0.0041 (4)	0.0061 (4)	−0.0152 (4)

O1—C11	1.3857 (11)	C9—C13	1.4658 (13)
O1—C19	1.4363 (13)	C10—C11	1.3895 (12)
O2—C13	1.2235 (12)	C10—C14	1.5155 (12)
N1—C12	1.3727 (11)	C11—C12	1.4018 (12)
N1—C1	1.3909 (12)	C13—H13A	0.9300
N1—H1N1	0.822 (17)	C14—C15	1.5071 (13)
C1—C2	1.3948 (13)	C14—H14A	0.9700
C1—C6	1.4113 (13)	C14—H14B	0.9700
C2—C3	1.3892 (14)	C15—C16	1.3360 (13)
C2—H2A	0.9300	C15—H15A	0.9300
C3—C4	1.3999 (15)	C16—C17	1.5035 (14)
C3—H3A	0.9300	C16—C18	1.5054 (14)
C4—C5	1.3895 (14)	C17—H17A	0.9600
C4—H4A	0.9300	C17—H17B	0.9600
C5—C6	1.3978 (13)	C17—H17C	0.9600
C5—H5A	0.9300	C18—H18A	0.9600
C6—C7	1.4500 (12)	C18—H18B	0.9600
C7—C8	1.3875 (12)	C18—H18C	0.9600
C7—C12	1.4167 (12)	C19—H19A	0.9600
C8—C9	1.3951 (13)	C19—H19B	0.9600
C8—H8A	0.9300	C19—H19C	0.9600
C9—C10	1.4271 (13)
C11—O1—C19	113.68 (8)	N1—C12—C11	128.96 (9)
C12—N1—C1	108.62 (8)	N1—C12—C7	109.54 (8)
C12—N1—H1N1	128.2 (11)	C11—C12—C7	121.50 (8)
C1—N1—H1N1	122.8 (11)	O2—C13—C9	124.13 (9)
N1—C1—C2	128.87 (9)	O2—C13—H13A	117.9
N1—C1—C6	109.20 (8)	C9—C13—H13A	117.9
C2—C1—C6	121.92 (9)	C15—C14—C10	112.82 (8)
C3—C2—C1	117.16 (9)	C15—C14—H14A	109.0
C3—C2—H2A	121.4	C10—C14—H14A	109.0
C1—C2—H2A	121.4	C15—C14—H14B	109.0
C2—C3—C4	121.77 (9)	C10—C14—H14B	109.0
C2—C3—H3A	119.1	H14A—C14—H14B	107.8
C4—C3—H3A	119.1	C16—C15—C14	127.08 (9)
C5—C4—C3	120.78 (9)	C16—C15—H15A	116.5
C5—C4—H4A	119.6	C14—C15—H15A	116.5
C3—C4—H4A	119.6	C15—C16—C17	124.45 (9)
C4—C5—C6	118.63 (9)	C15—C16—C18	120.70 (9)
C4—C5—H5A	120.7	C17—C16—C18	114.84 (9)
C6—C5—H5A	120.7	C16—C17—H17A	109.5
C5—C6—C1	119.73 (9)	C16—C17—H17B	109.5
C5—C6—C7	133.90 (9)	H17A—C17—H17B	109.5
C1—C6—C7	106.36 (8)	C16—C17—H17C	109.5
C8—C7—C12	119.22 (8)	H17A—C17—H17C	109.5
C8—C7—C6	134.49 (8)	H17B—C17—H17C	109.5
C12—C7—C6	106.27 (8)	C16—C18—H18A	109.5
C7—C8—C9	119.55 (8)	C16—C18—H18B	109.5
C7—C8—H8A	120.2	H18A—C18—H18B	109.5
C9—C8—H8A	120.2	C16—C18—H18C	109.5
C8—C9—C10	121.40 (8)	H18A—C18—H18C	109.5
C8—C9—C13	118.14 (8)	H18B—C18—H18C	109.5
C10—C9—C13	120.46 (8)	O1—C19—H19A	109.5
C11—C10—C9	118.94 (8)	O1—C19—H19B	109.5
C11—C10—C14	119.26 (8)	H19A—C19—H19B	109.5
C9—C10—C14	121.76 (8)	O1—C19—H19C	109.5
O1—C11—C10	120.95 (8)	H19A—C19—H19C	109.5
O1—C11—C12	119.63 (8)	H19B—C19—H19C	109.5
C10—C11—C12	119.33 (8)
C12—N1—C1—C2	179.57 (9)	C13—C9—C10—C14	−0.39 (13)
C12—N1—C1—C6	0.45 (10)	C19—O1—C11—C10	101.43 (10)
N1—C1—C2—C3	−179.21 (9)	C19—O1—C11—C12	−82.17 (11)
C6—C1—C2—C3	−0.19 (14)	C9—C10—C11—O1	173.69 (8)
C1—C2—C3—C4	0.09 (15)	C14—C10—C11—O1	−3.97 (13)
C2—C3—C4—C5	0.20 (15)	C9—C10—C11—C12	−2.73 (13)
C3—C4—C5—C6	−0.37 (14)	C14—C10—C11—C12	179.61 (8)
C4—C5—C6—C1	0.27 (14)	C1—N1—C12—C11	−179.49 (9)
C4—C5—C6—C7	179.54 (9)	C1—N1—C12—C7	−0.48 (10)
N1—C1—C6—C5	179.20 (8)	O1—C11—C12—N1	4.24 (15)
C2—C1—C6—C5	0.01 (14)	C10—C11—C12—N1	−179.30 (9)
N1—C1—C6—C7	−0.25 (10)	O1—C11—C12—C7	−174.67 (8)
C2—C1—C6—C7	−179.44 (8)	C10—C11—C12—C7	1.79 (14)
C5—C6—C7—C8	−0.63 (18)	C8—C7—C12—N1	−178.66 (8)
C1—C6—C7—C8	178.71 (10)	C6—C7—C12—N1	0.31 (10)
C5—C6—C7—C12	−179.38 (10)	C8—C7—C12—C11	0.44 (13)
C1—C6—C7—C12	−0.04 (10)	C6—C7—C12—C11	179.42 (8)
C12—C7—C8—C9	−1.64 (13)	C8—C9—C13—O2	−8.58 (14)
C6—C7—C8—C9	179.73 (9)	C10—C9—C13—O2	170.98 (9)
C7—C8—C9—C10	0.67 (13)	C11—C10—C14—C15	105.69 (10)
C7—C8—C9—C13	−179.77 (8)	C9—C10—C14—C15	−71.91 (11)
C8—C9—C10—C11	1.55 (13)	C10—C14—C15—C16	139.14 (10)
C13—C9—C10—C11	−177.99 (8)	C14—C15—C16—C17	−0.51 (17)
C8—C9—C10—C14	179.15 (8)	C14—C15—C16—C18	178.19 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2i	0.825 (19)	2.099 (19)	2.8843 (13)	158.8 (15)
C18—H18A···O1ii	0.96	2.59	3.5369 (15)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2i	0.825 (19)	2.099 (19)	2.8843 (13)	158.8 (15)
C18—H18A⋯O1ii	0.96	2.59	3.5369 (15)	168

Symmetry codes: (i) ; (ii) .