3-(9H-Carbazol-9-yl)propan-1-ol.

In the title compound, C(15)H(15)NO, the dihedral angle between the benzene rings is 2.25 (2)°. The C-C-C-O atoms of the propanol side chain are in a gauche conformation [torsion angle = -60.5 (2)°]. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into C(2) chains propagating in [100]. The O-bonded H atom is disordered over two sites of equal occupancy.

Related literature

For applications of the title compound, see: Chakkaravarthi et al. (2008 ▶); Murugavel et al. (2009 ▶). For related structures, see: Chen et al. (2009 ▶); Uludağ et al. (2010 ▶)

Experimental

Crystal data

C15H15NO

M = 225.28

Monoclinic,

a = 5.2930 (6) Å

b = 12.5935 (16) Å

c = 17.954 (2) Å

β = 97.778 (6)°

V = 1185.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.32 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.975, T max = 0.986

8147 measured reflections

2721 independent reflections

1566 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.142

S = 0.97

2721 reflections

162 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810051809/hb5760sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051809/hb5760Isup2.hkl

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

C15H15NO	F(000) = 480
Mr = 225.28	Dx = 1.262 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1647 reflections
a = 5.2930 (6) Å	θ = 2.3–23.5°
b = 12.5935 (16) Å	µ = 0.08 mm−1
c = 17.954 (2) Å	T = 298 K
β = 97.778 (6)°	Block, colourless
V = 1185.8 (3) Å3	0.32 × 0.20 × 0.18 mm
Z = 4

Bruker APEXII CCD diffractometer	2721 independent reflections
Radiation source: fine-focus sealed tube	1566 reflections with I > 2σ(I)
graphite	Rint = 0.041
phi and ω scans	θmax = 28.4°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −5→7
Tmin = 0.975, Tmax = 0.986	k = −16→16
8147 measured reflections	l = −23→23

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.0591P)2 + 0.2606P] where P = (Fo2 + 2Fc2)/3
2721 reflections	(Δ/σ)max < 0.001
162 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.21 e Å−3

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	Occ. (<1)
C1	0.2244 (4)	0.30270 (16)	0.27538 (14)	0.0562 (6)
H1	0.1063	0.3269	0.2360	0.067*
C2	0.2145 (5)	0.33733 (17)	0.34732 (16)	0.0648 (7)
H2	0.0895	0.3857	0.3565	0.078*
C3	0.3882 (5)	0.30124 (17)	0.40636 (14)	0.0630 (7)
H3	0.3773	0.3259	0.4546	0.076*
C4	0.5764 (4)	0.23001 (16)	0.39565 (12)	0.0519 (6)
H4	0.6922	0.2059	0.4357	0.062*
C5	0.5869 (3)	0.19539 (14)	0.32266 (11)	0.0395 (5)
C6	0.6937 (3)	0.11621 (14)	0.21952 (11)	0.0389 (5)
C7	0.8142 (4)	0.05761 (15)	0.16897 (12)	0.0484 (5)
H7	0.9554	0.0155	0.1851	0.058*
C8	0.7165 (5)	0.06429 (17)	0.09406 (12)	0.0562 (6)
H8	0.7949	0.0265	0.0590	0.067*
C9	0.5048 (5)	0.12569 (17)	0.06958 (13)	0.0589 (6)
H9	0.4426	0.1280	0.0186	0.071*
C10	0.3857 (4)	0.18309 (16)	0.11946 (12)	0.0527 (6)
H10	0.2430	0.2239	0.1026	0.063*
C11	0.4806 (3)	0.17964 (14)	0.19561 (11)	0.0407 (5)
C12	0.4124 (4)	0.23114 (14)	0.26192 (11)	0.0412 (5)
C13	0.9639 (3)	0.06950 (15)	0.34094 (11)	0.0429 (5)
H13A	1.0058	0.1062	0.3885	0.051*
H13B	1.1125	0.0724	0.3148	0.051*
C14	0.9059 (4)	−0.04550 (14)	0.35637 (11)	0.0436 (5)
H14A	0.8677	−0.0822	0.3087	0.052*
H14B	1.0576	−0.0778	0.3834	0.052*
C15	0.6889 (4)	−0.06224 (17)	0.40063 (12)	0.0502 (5)
H15A	0.5344	−0.0327	0.3732	0.060*
H15B	0.6623	−0.1378	0.4067	0.060*
N1	0.7554 (3)	0.12450 (12)	0.29658 (9)	0.0406 (4)
O1	0.7366 (3)	−0.01369 (15)	0.47257 (9)	0.0653 (5)
H1O	0.594 (9)	−0.009 (6)	0.500 (4)	0.13 (2)*	0.50
H1OA	0.903 (11)	−0.012 (5)	0.489 (4)	0.10 (2)*	0.50

	U11	U22	U33	U12	U13	U23
C1	0.0484 (13)	0.0443 (11)	0.0776 (18)	0.0071 (10)	0.0148 (12)	0.0099 (11)
C2	0.0610 (15)	0.0465 (12)	0.093 (2)	0.0095 (11)	0.0321 (15)	−0.0026 (13)
C3	0.0699 (16)	0.0525 (13)	0.0715 (17)	−0.0036 (13)	0.0278 (14)	−0.0149 (12)
C4	0.0557 (13)	0.0503 (12)	0.0503 (14)	−0.0030 (11)	0.0098 (10)	−0.0076 (10)
C5	0.0368 (10)	0.0359 (9)	0.0471 (12)	−0.0044 (9)	0.0107 (9)	−0.0025 (9)
C6	0.0355 (10)	0.0389 (10)	0.0431 (12)	−0.0057 (9)	0.0083 (9)	0.0016 (9)
C7	0.0475 (12)	0.0470 (11)	0.0528 (13)	−0.0013 (10)	0.0140 (10)	−0.0017 (10)
C8	0.0688 (15)	0.0580 (13)	0.0448 (13)	−0.0106 (12)	0.0180 (11)	−0.0064 (11)
C9	0.0740 (16)	0.0613 (13)	0.0401 (13)	−0.0118 (13)	0.0027 (11)	0.0020 (11)
C10	0.0504 (12)	0.0521 (12)	0.0533 (14)	−0.0071 (10)	−0.0010 (10)	0.0114 (11)
C11	0.0364 (11)	0.0382 (10)	0.0469 (12)	−0.0067 (9)	0.0040 (9)	0.0061 (9)
C12	0.0369 (10)	0.0338 (9)	0.0538 (13)	−0.0016 (9)	0.0088 (9)	0.0057 (9)
C13	0.0290 (10)	0.0519 (11)	0.0473 (12)	−0.0002 (9)	0.0035 (9)	0.0020 (9)
C14	0.0404 (11)	0.0466 (11)	0.0439 (12)	0.0040 (9)	0.0059 (9)	0.0008 (9)
C15	0.0401 (12)	0.0574 (12)	0.0524 (14)	−0.0080 (10)	0.0034 (10)	0.0019 (10)
N1	0.0378 (9)	0.0430 (8)	0.0408 (10)	0.0041 (7)	0.0043 (7)	−0.0014 (7)
O1	0.0512 (11)	0.0989 (13)	0.0473 (10)	−0.0058 (10)	0.0125 (8)	−0.0059 (9)

C1—C2	1.371 (3)	C9—C10	1.369 (3)
C1—C12	1.387 (3)	C9—H9	0.9300
C1—H1	0.9300	C10—C11	1.392 (3)
C2—C3	1.383 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.444 (3)
C3—C4	1.373 (3)	C13—N1	1.447 (2)
C3—H3	0.9300	C13—C14	1.514 (2)
C4—C5	1.389 (3)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—N1	1.388 (2)	C14—C15	1.497 (3)
C5—C12	1.405 (3)	C14—H14A	0.9700
C6—N1	1.382 (2)	C14—H14B	0.9700
C6—C7	1.390 (3)	C15—O1	1.420 (3)
C6—C11	1.401 (3)	C15—H15A	0.9700
C7—C8	1.377 (3)	C15—H15B	0.9700
C7—H7	0.9300	O1—H1O	0.95 (2)
C8—C9	1.383 (3)	O1—H1OA	0.89 (6)
C8—H8	0.9300
C2—C1—C12	119.4 (2)	C10—C11—C6	119.15 (18)
C2—C1—H1	120.3	C10—C11—C12	134.31 (18)
C12—C1—H1	120.3	C6—C11—C12	106.52 (17)
C1—C2—C3	120.8 (2)	C1—C12—C5	118.99 (19)
C1—C2—H2	119.6	C1—C12—C11	134.5 (2)
C3—C2—H2	119.6	C5—C12—C11	106.53 (16)
C4—C3—C2	121.8 (2)	N1—C13—C14	113.60 (15)
C4—C3—H3	119.1	N1—C13—H13A	108.8
C2—C3—H3	119.1	C14—C13—H13A	108.8
C3—C4—C5	117.3 (2)	N1—C13—H13B	108.8
C3—C4—H4	121.3	C14—C13—H13B	108.8
C5—C4—H4	121.3	H13A—C13—H13B	107.7
N1—C5—C4	129.05 (19)	C15—C14—C13	114.89 (16)
N1—C5—C12	109.24 (17)	C15—C14—H14A	108.5
C4—C5—C12	121.72 (18)	C13—C14—H14A	108.5
N1—C6—C7	128.79 (18)	C15—C14—H14B	108.5
N1—C6—C11	109.58 (16)	C13—C14—H14B	108.5
C7—C6—C11	121.62 (19)	H14A—C14—H14B	107.5
C8—C7—C6	117.4 (2)	O1—C15—C14	111.54 (16)
C8—C7—H7	121.3	O1—C15—H15A	109.3
C6—C7—H7	121.3	C14—C15—H15A	109.3
C7—C8—C9	121.7 (2)	O1—C15—H15B	109.3
C7—C8—H8	119.1	C14—C15—H15B	109.3
C9—C8—H8	119.1	H15A—C15—H15B	108.0
C10—C9—C8	120.8 (2)	C6—N1—C5	108.11 (15)
C10—C9—H9	119.6	C6—N1—C13	125.06 (15)
C8—C9—H9	119.6	C5—N1—C13	126.82 (16)
C9—C10—C11	119.3 (2)	C15—O1—H1O	116 (5)
C9—C10—H10	120.4	C15—O1—H1OA	111 (5)
C11—C10—H10	120.4	H1O—O1—H1OA	130 (7)
C12—C1—C2—C3	−0.4 (3)	C4—C5—C12—C1	−0.1 (3)
C1—C2—C3—C4	0.1 (3)	N1—C5—C12—C11	−0.46 (19)
C2—C3—C4—C5	0.2 (3)	C4—C5—C12—C11	179.76 (16)
C3—C4—C5—N1	−179.93 (18)	C10—C11—C12—C1	1.0 (4)
C3—C4—C5—C12	−0.2 (3)	C6—C11—C12—C1	179.4 (2)
N1—C6—C7—C8	−178.94 (18)	C10—C11—C12—C5	−178.9 (2)
C11—C6—C7—C8	0.1 (3)	C6—C11—C12—C5	−0.46 (19)
C6—C7—C8—C9	−0.8 (3)	N1—C13—C14—C15	−61.9 (2)
C7—C8—C9—C10	0.6 (3)	C13—C14—C15—O1	−60.5 (2)
C8—C9—C10—C11	0.3 (3)	C7—C6—N1—C5	177.62 (18)
C9—C10—C11—C6	−0.9 (3)	C11—C6—N1—C5	−1.5 (2)
C9—C10—C11—C12	177.4 (2)	C7—C6—N1—C13	−1.3 (3)
N1—C6—C11—C10	179.95 (16)	C11—C6—N1—C13	179.56 (16)
C7—C6—C11—C10	0.7 (3)	C4—C5—N1—C6	−179.01 (18)
N1—C6—C11—C12	1.23 (19)	C12—C5—N1—C6	1.22 (19)
C7—C6—C11—C12	−178.00 (16)	C4—C5—N1—C13	−0.1 (3)
C2—C1—C12—C5	0.4 (3)	C12—C5—N1—C13	−179.89 (16)
C2—C1—C12—C11	−179.4 (2)	C14—C13—N1—C6	−78.8 (2)
N1—C5—C12—C1	179.64 (15)	C14—C13—N1—C5	102.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O1i	0.95 (2)	1.91 (3)	2.834 (3)	163 (6)
O1—H1OA···O1ii	0.89 (6)	1.96 (6)	2.850 (4)	172 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O1i	0.95 (2)	1.91 (3)	2.834 (3)	163 (6)
O1—H1OA⋯O1ii	0.89 (6)	1.96 (6)	2.850 (4)	172 (6)

Symmetry codes: (i) ; (ii) .