11-Butyl-3-meth-oxy-11H-benzo[a]carbazole.

The title compound, C(21)H(21)NO, consists of a carbazole skeleton with a meth-oxy-benzene ring fused to the carbazole, and a butyl group attached to the carbazole N atom. The carbazole skeleton is nearly planar [maximum deviation = 0.078 (2) Å], and it is oriented at a dihedral angle of 4.22 (4)° with respect to the adjacent meth-oxy-benzene ring.

Related literature

For the biological activity of carbazole derivatives, see: Knölker & Reddy (2002 ▶). For the use of carbazole derivatives in the syntheses of indole alkaloids, see: Routier et al. (2001 ▶). For the use of benzo[a]carbazoles in cancer treatment, see: Carini et al. (2001 ▶). For the anti­tumor activity of a series of simple benzo[a]carbazoles against mammary tumors of rats, leukemia, renal tumors, colon cancer and malignant melanoma tumor cell lines, see: von Angerer & Prekajac (1986 ▶); Pindur & Lemster (1997 ▶). For the extensive application of benzo[a]carbazole derivatives as photographic materials, see: Oliveira et al. (2005 ▶. For tetra­hydro­carbazole systems present in the frameworks of a number of indole-type alkaloids of biological inter­est, see: Phillipson & Zenk (1980 ▶); Saxton (1983 ▶); Abraham (1975 ▶). For related structures, see: Hökelek et al. (1994 ▶, 1998 ▶, 1999 ▶, 2004 ▶, 2006 ▶); Patır et al. (1997 ▶); Hökelek & Patır (1999 ▶, 2002 ▶); Çaylak et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H21NO

M = 303.39

Monoclinic,

a = 10.7263 (6) Å

b = 5.5562 (3) Å

c = 13.8967 (7) Å

β = 97.841 (2)°

V = 820.46 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.48 × 0.39 × 0.35 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.965, T max = 0.974

7947 measured reflections

2248 independent reflections

2001 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.091

S = 1.04

2248 reflections

270 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021963/xu2773sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021963/xu2773Isup2.hkl

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

C21H21NO	F(000) = 324
Mr = 303.39	Dx = 1.228 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3840 reflections
a = 10.7263 (6) Å	θ = 2.3–28.4°
b = 5.5562 (3) Å	µ = 0.08 mm−1
c = 13.8967 (7) Å	T = 100 K
β = 97.841 (2)°	Block, colorless
V = 820.46 (8) Å3	0.48 × 0.39 × 0.35 mm
Z = 2

Bruker Kappa APEXII CCD area-detector diffractometer	2248 independent reflections
Radiation source: fine-focus sealed tube	2001 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 28.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→14
Tmin = 0.965, Tmax = 0.974	k = −7→6
7947 measured reflections	l = −17→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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0528P)2 + 0.1088P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2248 reflections	Δρmax = 0.25 e Å−3
270 parameters	Δρmin = −0.16 e Å−3
Primary atom site location: structure-invariant direct methods

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	0.59965 (11)	0.9420 (3)	−0.11895 (9)	0.0299 (3)
C1	1.02958 (17)	0.2221 (4)	0.41676 (13)	0.0246 (4)
H1	0.9764 (19)	0.094 (5)	0.4258 (15)	0.030 (6)*
C2	1.14448 (17)	0.2475 (4)	0.47538 (13)	0.0276 (4)
H2	1.166 (2)	0.136 (5)	0.5266 (17)	0.042 (7)*
C3	1.22609 (17)	0.4381 (4)	0.46185 (13)	0.0271 (4)
H3	1.3035 (19)	0.447 (4)	0.5040 (14)	0.022 (5)*
C4	1.19492 (16)	0.6061 (4)	0.38921 (13)	0.0245 (4)
H4	1.2520 (17)	0.742 (4)	0.3796 (13)	0.021 (5)*
C4A	1.08080 (15)	0.5806 (4)	0.32759 (12)	0.0217 (4)
C5	1.06152 (16)	0.9086 (4)	0.19246 (13)	0.0232 (4)
H5	1.1411 (18)	0.992 (4)	0.2181 (13)	0.020 (5)*
C5A	1.02208 (15)	0.7091 (3)	0.24338 (12)	0.0210 (4)
C6	0.98899 (16)	0.9848 (4)	0.10954 (13)	0.0238 (4)
H6	1.0136 (18)	1.120 (5)	0.0755 (14)	0.025 (5)*
C7	0.87121 (15)	0.8724 (4)	0.07581 (12)	0.0215 (4)
C8	0.82600 (15)	0.6754 (4)	0.12711 (12)	0.0205 (4)
C8A	0.90768 (15)	0.5921 (4)	0.21092 (12)	0.0197 (3)
C9A	0.99973 (15)	0.3887 (4)	0.34259 (12)	0.0214 (4)
N9	0.89451 (13)	0.3987 (3)	0.27259 (10)	0.0209 (3)
C10	0.79576 (15)	0.2165 (4)	0.26464 (13)	0.0221 (4)
H101	0.8331 (18)	0.076 (5)	0.2927 (14)	0.021 (5)*
H102	0.7675 (17)	0.185 (4)	0.1949 (14)	0.021 (5)*
C11	0.68345 (16)	0.2861 (4)	0.31519 (13)	0.0228 (4)
H111	0.7121 (18)	0.304 (4)	0.3868 (14)	0.023 (5)*
H112	0.6483 (19)	0.442 (5)	0.2886 (15)	0.027 (6)*
C12	0.58043 (17)	0.0964 (4)	0.29886 (15)	0.0290 (4)
H121	0.6196 (19)	−0.064 (5)	0.3171 (14)	0.025 (5)*
H122	0.5517 (19)	0.077 (5)	0.2304 (17)	0.036 (6)*
C13	0.47038 (18)	0.1518 (5)	0.35479 (16)	0.0397 (5)
H13A	0.4050	0.0290	0.3400	0.060*
H13B	0.4355	0.3104	0.3355	0.060*
H13C	0.5002	0.1516	0.4247	0.060*
C14	0.70388 (16)	0.5850 (4)	0.09343 (13)	0.0248 (4)
H14	0.668 (2)	0.458 (5)	0.1282 (15)	0.032 (6)*
C15	0.63327 (16)	0.6779 (4)	0.01272 (13)	0.0264 (4)
H15	0.549 (2)	0.613 (5)	−0.0092 (17)	0.044 (7)*
C16	0.68014 (16)	0.8672 (4)	−0.03944 (12)	0.0242 (4)
C17	0.79658 (16)	0.9641 (4)	−0.00876 (12)	0.0235 (4)
H17	0.8282 (16)	1.097 (4)	−0.0415 (13)	0.015 (5)*
C18	0.63988 (18)	1.1414 (4)	−0.17108 (14)	0.0325 (5)
H18A	0.5741	1.1833	−0.2245	0.049*
H18B	0.7172	1.0988	−0.1974	0.049*
H18C	0.6561	1.2794	−0.1272	0.049*

	U11	U22	U33	U12	U13	U23
O1	0.0241 (6)	0.0399 (9)	0.0257 (6)	0.0017 (6)	0.0027 (5)	0.0051 (7)
C1	0.0267 (9)	0.0213 (10)	0.0275 (8)	0.0008 (8)	0.0096 (7)	−0.0004 (8)
C2	0.0292 (9)	0.0284 (11)	0.0259 (9)	0.0058 (8)	0.0057 (7)	0.0023 (8)
C3	0.0228 (8)	0.0342 (12)	0.0250 (8)	0.0021 (8)	0.0062 (7)	−0.0029 (9)
C4	0.0212 (8)	0.0280 (11)	0.0253 (8)	−0.0024 (8)	0.0071 (6)	−0.0025 (8)
C4A	0.0222 (8)	0.0219 (9)	0.0223 (8)	0.0003 (7)	0.0077 (6)	−0.0039 (8)
C5	0.0215 (8)	0.0229 (9)	0.0263 (8)	−0.0032 (7)	0.0075 (7)	−0.0025 (8)
C5A	0.0197 (7)	0.0218 (9)	0.0229 (8)	0.0002 (7)	0.0072 (6)	−0.0024 (7)
C6	0.0262 (8)	0.0209 (9)	0.0261 (9)	−0.0032 (8)	0.0100 (7)	0.0006 (8)
C7	0.0215 (8)	0.0226 (10)	0.0220 (8)	0.0009 (7)	0.0088 (7)	−0.0025 (7)
C8	0.0207 (7)	0.0203 (9)	0.0215 (8)	0.0008 (7)	0.0065 (6)	−0.0024 (7)
C8A	0.0203 (7)	0.0178 (9)	0.0225 (8)	0.0001 (7)	0.0081 (6)	−0.0021 (7)
C9A	0.0199 (7)	0.0217 (9)	0.0239 (8)	0.0016 (7)	0.0076 (6)	−0.0015 (7)
N9	0.0204 (6)	0.0186 (8)	0.0240 (7)	−0.0017 (6)	0.0045 (5)	0.0000 (6)
C10	0.0210 (8)	0.0189 (9)	0.0269 (9)	−0.0034 (7)	0.0051 (7)	−0.0001 (8)
C11	0.0212 (8)	0.0226 (10)	0.0252 (9)	−0.0026 (7)	0.0054 (6)	0.0003 (7)
C12	0.0230 (8)	0.0338 (12)	0.0307 (10)	−0.0073 (8)	0.0051 (7)	−0.0015 (9)
C13	0.0246 (9)	0.0471 (15)	0.0491 (12)	−0.0051 (10)	0.0112 (8)	0.0041 (11)
C14	0.0247 (8)	0.0265 (10)	0.0240 (8)	−0.0033 (8)	0.0062 (6)	0.0006 (8)
C15	0.0201 (8)	0.0323 (11)	0.0272 (9)	−0.0018 (8)	0.0049 (7)	−0.0012 (8)
C16	0.0235 (8)	0.0286 (10)	0.0211 (8)	0.0045 (7)	0.0051 (7)	−0.0009 (8)
C17	0.0246 (8)	0.0240 (10)	0.0234 (8)	0.0005 (7)	0.0087 (6)	−0.0008 (8)
C18	0.0324 (9)	0.0366 (12)	0.0283 (9)	0.0040 (9)	0.0035 (8)	0.0064 (9)

O1—C16	1.371 (2)	C10—C11	1.525 (2)
O1—C18	1.422 (3)	C10—H101	0.94 (2)
C1—C2	1.389 (3)	C10—H102	0.991 (19)
C1—H1	0.93 (2)	C11—C12	1.521 (3)
C2—C3	1.403 (3)	C11—H111	1.006 (19)
C2—H2	0.95 (3)	C11—H112	0.99 (3)
C3—C4	1.382 (3)	C12—C13	1.530 (3)
C3—H3	0.95 (2)	C12—H121	1.00 (2)
C4—H4	0.99 (2)	C12—H122	0.97 (2)
C4A—C4	1.402 (2)	C13—H13A	0.9800
C4A—C9A	1.410 (3)	C13—H13B	0.9800
C5—C5A	1.411 (3)	C13—H13C	0.9800
C5—H5	1.00 (2)	C14—C8	1.421 (2)
C5A—C4A	1.440 (2)	C14—H14	0.97 (2)
C6—C5	1.367 (3)	C15—C14	1.366 (3)
C6—H6	0.95 (2)	C15—H15	0.98 (2)
C7—C6	1.430 (2)	C16—C15	1.408 (3)
C8—C7	1.427 (2)	C16—C17	1.373 (3)
C8—C8A	1.435 (2)	C17—C7	1.423 (3)
C8A—C5A	1.408 (2)	C17—H17	0.96 (2)
C9A—C1	1.390 (3)	C18—H18A	0.9800
N9—C8A	1.393 (2)	C18—H18B	0.9800
N9—C9A	1.387 (2)	C18—H18C	0.9800
N9—C10	1.458 (2)
C16—O1—C18	116.45 (15)	N9—C10—H101	106.4 (12)
C2—C1—C9A	117.62 (18)	N9—C10—H102	108.7 (12)
C2—C1—H1	120.6 (13)	C11—C10—H101	109.8 (12)
C9A—C1—H1	121.7 (13)	C11—C10—H102	109.9 (11)
C1—C2—C3	121.20 (18)	H101—C10—H102	108.3 (19)
C1—C2—H2	119.0 (15)	C10—C11—H111	109.1 (11)
C3—C2—H2	119.8 (15)	C10—C11—H112	109.4 (12)
C2—C3—H3	117.8 (14)	C12—C11—C10	111.04 (16)
C4—C3—C2	120.97 (17)	C12—C11—H111	109.5 (13)
C4—C3—H3	121.2 (14)	C12—C11—H112	108.4 (13)
C3—C4—C4A	118.82 (18)	H112—C11—H111	109.4 (18)
C3—C4—H4	121.4 (11)	C11—C12—C13	112.32 (18)
C4A—C4—H4	119.8 (11)	C11—C12—H121	107.9 (12)
C4—C4A—C5A	134.01 (18)	C11—C12—H122	110.6 (15)
C4—C4A—C9A	119.40 (17)	C13—C12—H121	112.1 (12)
C9A—C4A—C5A	106.56 (14)	C13—C12—H122	111.0 (13)
C5A—C5—H5	119.3 (12)	H121—C12—H122	103 (2)
C6—C5—C5A	119.41 (17)	C12—C13—H13A	109.5
C6—C5—H5	121.3 (12)	C12—C13—H13B	109.5
C5—C5A—C4A	132.01 (16)	C12—C13—H13C	109.5
C8A—C5A—C4A	107.26 (16)	H13A—C13—H13B	109.5
C8A—C5A—C5	120.68 (16)	H13A—C13—H13C	109.5
C5—C6—C7	121.13 (17)	H13B—C13—H13C	109.5
C5—C6—H6	120.2 (12)	C8—C14—H14	120.6 (13)
C7—C6—H6	118.5 (12)	C15—C14—C8	121.32 (18)
C8—C7—C6	121.11 (16)	C15—C14—H14	118.1 (13)
C17—C7—C6	119.12 (17)	C14—C15—C16	120.52 (17)
C17—C7—C8	119.75 (16)	C14—C15—H15	120.0 (16)
C7—C8—C8A	116.20 (15)	C16—C15—H15	119.5 (15)
C14—C8—C7	117.85 (17)	O1—C16—C15	114.31 (16)
C14—C8—C8A	125.91 (17)	O1—C16—C17	125.26 (18)
C5A—C8A—C8	121.33 (16)	C17—C16—C15	120.42 (17)
N9—C8A—C5A	108.44 (15)	C7—C17—H17	118.4 (11)
N9—C8A—C8	130.23 (16)	C16—C17—C7	120.08 (18)
C1—C9A—C4A	121.96 (16)	C16—C17—H17	121.5 (11)
N9—C9A—C1	129.06 (17)	O1—C18—H18A	109.5
N9—C9A—C4A	108.98 (15)	O1—C18—H18B	109.5
C8A—N9—C10	128.47 (14)	O1—C18—H18C	109.5
C9A—N9—C8A	108.74 (14)	H18A—C18—H18B	109.5
C9A—N9—C10	122.57 (15)	H18A—C18—H18C	109.5
N9—C10—C11	113.60 (15)	H18B—C18—H18C	109.5
C18—O1—C16—C15	176.75 (16)	N9—C8A—C5A—C4A	0.40 (19)
C18—O1—C16—C17	−2.2 (3)	N9—C8A—C5A—C5	178.18 (16)
C9A—C1—C2—C3	1.6 (3)	C8—C8A—C5A—C4A	−179.64 (15)
C1—C2—C3—C4	−0.4 (3)	C8—C8A—C5A—C5	−1.9 (3)
C2—C3—C4—C4A	−1.2 (3)	N9—C9A—C1—C2	177.47 (17)
C5A—C4A—C4—C3	−176.09 (19)	C4A—C9A—C1—C2	−1.3 (3)
C9A—C4A—C4—C3	1.5 (2)	C9A—N9—C8A—C5A	−1.06 (18)
C4—C4A—C9A—N9	−179.24 (16)	C9A—N9—C8A—C8	178.97 (17)
C4—C4A—C9A—C1	−0.2 (2)	C10—N9—C8A—C5A	−175.70 (16)
C5A—C4A—C9A—N9	−1.06 (18)	C10—N9—C8A—C8	4.3 (3)
C5A—C4A—C9A—C1	177.96 (16)	C8A—N9—C9A—C1	−177.60 (17)
C6—C5—C5A—C4A	175.63 (18)	C8A—N9—C9A—C4A	1.33 (18)
C6—C5—C5A—C8A	−1.5 (3)	C10—N9—C9A—C1	−2.6 (3)
C5—C5A—C4A—C4	0.8 (3)	C10—N9—C9A—C4A	176.34 (15)
C5—C5A—C4A—C9A	−177.03 (18)	C9A—N9—C10—C11	96.69 (19)
C8A—C5A—C4A—C4	178.20 (19)	C8A—N9—C10—C11	−89.3 (2)
C8A—C5A—C4A—C9A	0.40 (19)	N9—C10—C11—C12	176.39 (15)
C7—C6—C5—C5A	2.7 (3)	C10—C11—C12—C13	175.83 (17)
C8—C7—C6—C5	−0.6 (3)	C15—C14—C8—C7	2.1 (3)
C17—C7—C6—C5	177.50 (17)	C15—C14—C8—C8A	179.73 (17)
C8A—C8—C7—C6	−2.6 (2)	C16—C15—C14—C8	−0.1 (3)
C8A—C8—C7—C17	179.29 (16)	O1—C16—C15—C14	179.77 (17)
C14—C8—C7—C6	175.24 (16)	C17—C16—C15—C14	−1.3 (3)
C14—C8—C7—C17	−2.8 (2)	O1—C16—C17—C7	179.31 (16)
C7—C8—C8A—N9	−176.22 (16)	C15—C16—C17—C7	0.5 (3)
C7—C8—C8A—C5A	3.8 (2)	C16—C17—C7—C6	−176.50 (16)
C14—C8—C8A—N9	6.1 (3)	C16—C17—C7—C8	1.6 (3)
C14—C8—C8A—C5A	−173.86 (17)