3-[2-(9-Ethyl-9H-carbazol-3-yl)-6-methyl-3-quinol-yl]propan-1-ol.

In the title compound, C(27)H(26)N(2)O, the mean planes through the carbazole and quinoline ring systems form a dihedral angle of 67.23 (5)°. Mol-ecules are linked into cyclic centrosymmetric dimers by O-H⋯N hydrogen bonds, and C-H⋯π inter-actions with the pyridine ring of the quinoline ring system as an acceptor. The dimers are linked through C-H⋯O hydrogen bonds.

Related literature

For the biological activity and applications of carbazole derivatives, see: Itoigawa et al. (2000 ▶); Tachibana et al. (2001 ▶); Ramsewak et al. (1999 ▶); Friend et al. (1999 ▶); Diaz et al. (2002 ▶); Zhang et al. (2004 ▶). For the biological properties of quinoline derivatives, see: Cunico et al. (2006 ▶); Hartline et al. (2005 ▶). For related structures, see: Murugavel et al. (2008 ▶); Chakkaravarthi et al. (2008 ▶).

Experimental

Crystal data

C27H26N2O

M = 394.50

Monoclinic,

a = 13.6417 (5) Å

b = 9.8599 (3) Å

c = 16.3208 (5) Å

β = 109.658 (2)°

V = 2067.30 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.21 × 0.19 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.984, T max = 0.987

27360 measured reflections

6459 independent reflections

3912 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.228

S = 1.02

6459 reflections

316 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.67 e Å−3

Δρmin = −0.39 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 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042153/ci2733sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042153/ci2733Isup2.hkl

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

C27H26N2O	F(000) = 840
Mr = 394.50	Dx = 1.268 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6459 reflections
a = 13.6417 (5) Å	θ = 1.6–30.8°
b = 9.8599 (3) Å	µ = 0.08 mm−1
c = 16.3208 (5) Å	T = 293 K
β = 109.658 (2)°	Block, colourless
V = 2067.30 (12) Å3	0.21 × 0.19 × 0.17 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	6459 independent reflections
Radiation source: fine-focus sealed tube	3912 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω scans	θmax = 30.8°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.984, Tmax = 0.987	k = −14→13
27360 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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.228	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.1233P)2 + 0.4813P] where P = (Fo2 + 2Fc2)/3
6459 reflections	(Δ/σ)max = 0.006
316 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.38 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
C1	0.93457 (15)	1.0043 (2)	0.38448 (12)	0.0457 (4)
C2	1.02298 (17)	1.0150 (3)	0.36015 (14)	0.0593 (6)
C3	1.0529 (2)	0.9032 (3)	0.32531 (16)	0.0702 (7)
C4	0.9975 (2)	0.7822 (3)	0.31265 (16)	0.0682 (7)
C5	0.90952 (18)	0.7707 (2)	0.33655 (14)	0.0545 (5)
C6	0.87763 (14)	0.8820 (2)	0.37340 (11)	0.0435 (4)
C7	0.79523 (13)	0.90547 (18)	0.40869 (11)	0.0392 (4)
C8	0.71771 (14)	0.82534 (18)	0.42123 (12)	0.0404 (4)
C9	0.65428 (13)	0.87827 (17)	0.46436 (12)	0.0393 (4)
C10	0.66606 (15)	1.01400 (19)	0.49038 (14)	0.0455 (4)
C11	0.74047 (15)	1.09668 (19)	0.47741 (14)	0.0471 (4)
C12	0.80606 (14)	1.04043 (19)	0.43802 (12)	0.0417 (4)
C13	0.92173 (18)	1.2385 (2)	0.44090 (15)	0.0562 (5)
H13A	0.9950	1.2464	0.4479	0.067*
H13B	0.9135	1.2646	0.4955	0.067*
C14	0.8608 (2)	1.3349 (3)	0.37111 (17)	0.0729 (7)
H14A	0.8850	1.4257	0.3870	0.109*
H14B	0.7883	1.3291	0.3646	0.109*
H14C	0.8701	1.3114	0.3171	0.109*
C15	0.57097 (13)	0.79261 (17)	0.47778 (11)	0.0369 (4)
C16	0.57191 (13)	0.75609 (17)	0.56270 (11)	0.0382 (4)
C17	0.49310 (14)	0.67525 (18)	0.56791 (11)	0.0391 (4)
C18	0.41231 (13)	0.63336 (16)	0.49268 (11)	0.0364 (3)
C19	0.41835 (13)	0.67418 (17)	0.41187 (11)	0.0385 (4)
C20	0.33782 (17)	0.6347 (2)	0.33508 (13)	0.0514 (5)
C21	0.25614 (17)	0.5612 (2)	0.33960 (15)	0.0555 (5)
C22	0.24826 (15)	0.52069 (19)	0.42029 (14)	0.0479 (4)
C23	0.32661 (15)	0.55485 (18)	0.49506 (13)	0.0437 (4)
C24	0.15449 (18)	0.4418 (2)	0.42195 (18)	0.0658 (6)
H24A	0.1392	0.4643	0.4736	0.099*
H24B	0.1686	0.3464	0.4217	0.099*
H24C	0.0959	0.4643	0.3716	0.099*
C25	0.65808 (16)	0.7989 (2)	0.64488 (13)	0.0507 (5)
H25A	0.7222	0.8040	0.6317	0.061*
H25B	0.6669	0.7274	0.6876	0.061*
C26	0.6451 (2)	0.9318 (3)	0.68702 (16)	0.0670 (6)
H26A	0.7073	0.9479	0.7368	0.080*
H26B	0.6398	1.0046	0.6457	0.080*
C27	0.5535 (2)	0.9385 (3)	0.71641 (16)	0.0662 (6)
H27A	0.4904	0.9212	0.6677	0.079*
H27B	0.5594	0.8698	0.7604	0.079*
N1	0.89013 (12)	1.09912 (16)	0.42253 (11)	0.0472 (4)
N2	0.49803 (12)	0.75259 (15)	0.40562 (9)	0.0403 (3)
O1	0.5485 (2)	1.0718 (2)	0.75206 (12)	0.0920 (7)
H1	0.5430	1.1294	0.7145	0.138*
H5	0.8714 (18)	0.687 (3)	0.3262 (15)	0.054 (6)*
H8	0.7093 (18)	0.729 (2)	0.4023 (15)	0.055 (6)*
H11	0.7485 (17)	1.189 (3)	0.4958 (14)	0.054 (6)*
H23	0.3214 (17)	0.525 (2)	0.5550 (15)	0.053 (6)*
H2	1.061 (2)	1.098 (3)	0.3724 (15)	0.058 (7)*
H4	1.025 (2)	0.702 (3)	0.2924 (18)	0.077 (8)*
H10	0.621 (2)	1.054 (2)	0.5176 (15)	0.062 (7)*
H17	0.4891 (16)	0.649 (2)	0.6239 (14)	0.046 (5)*
H3	1.116 (2)	0.910 (3)	0.309 (2)	0.090 (9)*
H20	0.342 (2)	0.653 (3)	0.2771 (19)	0.079 (8)*
H21	0.196 (2)	0.546 (3)	0.2859 (17)	0.073 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.0384 (9)	0.0591 (11)	0.0381 (9)	0.0007 (8)	0.0111 (7)	0.0064 (8)
C2	0.0450 (11)	0.0906 (17)	0.0447 (10)	−0.0091 (11)	0.0181 (9)	0.0069 (11)
C3	0.0557 (14)	0.110 (2)	0.0526 (12)	−0.0038 (13)	0.0286 (11)	−0.0064 (13)
C4	0.0649 (15)	0.0946 (19)	0.0524 (12)	0.0144 (14)	0.0292 (11)	−0.0067 (12)
C5	0.0568 (12)	0.0616 (13)	0.0482 (11)	0.0054 (10)	0.0218 (9)	−0.0026 (9)
C6	0.0396 (9)	0.0535 (10)	0.0372 (8)	0.0047 (7)	0.0125 (7)	0.0046 (7)
C7	0.0368 (9)	0.0408 (9)	0.0395 (8)	0.0040 (6)	0.0122 (7)	0.0028 (7)
C8	0.0416 (9)	0.0356 (8)	0.0447 (9)	0.0021 (7)	0.0156 (7)	0.0006 (7)
C9	0.0360 (8)	0.0386 (8)	0.0444 (9)	0.0018 (6)	0.0149 (7)	0.0024 (7)
C10	0.0396 (10)	0.0417 (9)	0.0580 (11)	0.0036 (7)	0.0204 (8)	−0.0029 (8)
C11	0.0442 (10)	0.0349 (9)	0.0627 (12)	0.0002 (7)	0.0188 (9)	−0.0043 (8)
C12	0.0366 (8)	0.0406 (9)	0.0456 (9)	−0.0004 (7)	0.0107 (7)	0.0053 (7)
C13	0.0564 (12)	0.0512 (11)	0.0601 (12)	−0.0159 (9)	0.0183 (10)	−0.0019 (9)
C14	0.0953 (19)	0.0568 (14)	0.0723 (16)	0.0008 (13)	0.0358 (14)	0.0139 (11)
C15	0.0368 (8)	0.0348 (8)	0.0409 (8)	0.0033 (6)	0.0157 (7)	−0.0005 (6)
C16	0.0386 (8)	0.0368 (8)	0.0386 (8)	0.0049 (6)	0.0122 (7)	−0.0020 (6)
C17	0.0455 (9)	0.0383 (8)	0.0358 (8)	0.0037 (7)	0.0166 (7)	0.0006 (6)
C18	0.0391 (8)	0.0316 (7)	0.0407 (8)	0.0025 (6)	0.0165 (7)	−0.0008 (6)
C19	0.0398 (9)	0.0379 (8)	0.0388 (8)	0.0007 (7)	0.0146 (7)	−0.0013 (6)
C20	0.0533 (11)	0.0585 (12)	0.0385 (9)	−0.0072 (9)	0.0101 (8)	−0.0015 (8)
C21	0.0496 (11)	0.0551 (12)	0.0531 (11)	−0.0079 (9)	0.0059 (9)	−0.0055 (9)
C22	0.0431 (10)	0.0370 (9)	0.0636 (12)	−0.0020 (7)	0.0178 (9)	−0.0029 (8)
C23	0.0456 (10)	0.0360 (8)	0.0536 (10)	0.0009 (7)	0.0222 (8)	0.0022 (7)
C24	0.0532 (13)	0.0551 (13)	0.0873 (17)	−0.0124 (10)	0.0214 (12)	−0.0005 (12)
C25	0.0516 (11)	0.0511 (11)	0.0438 (10)	−0.0017 (8)	0.0086 (8)	−0.0059 (8)
C26	0.0769 (16)	0.0637 (14)	0.0556 (13)	−0.0054 (12)	0.0160 (11)	−0.0107 (10)
C27	0.0820 (17)	0.0611 (14)	0.0537 (12)	0.0008 (12)	0.0203 (12)	0.0013 (10)
N1	0.0416 (8)	0.0478 (9)	0.0525 (9)	−0.0064 (6)	0.0163 (7)	0.0038 (7)
N2	0.0428 (8)	0.0422 (8)	0.0375 (7)	−0.0012 (6)	0.0155 (6)	0.0008 (6)
O1	0.161 (2)	0.0715 (12)	0.0560 (10)	0.0272 (13)	0.0528 (12)	−0.0011 (8)

C1—N1	1.372 (3)	C15—N2	1.321 (2)
C1—C2	1.395 (3)	C15—C16	1.428 (2)
C1—C6	1.413 (3)	C16—C17	1.364 (3)
C2—C3	1.364 (4)	C16—C25	1.516 (2)
C2—H2	0.95 (2)	C17—C18	1.408 (2)
C3—C4	1.390 (4)	C17—H17	0.97 (2)
C3—H3	0.99 (3)	C18—C19	1.408 (2)
C4—C5	1.385 (4)	C18—C23	1.414 (2)
C4—H4	0.98 (3)	C19—N2	1.365 (2)
C5—C6	1.390 (3)	C19—C20	1.415 (3)
C5—H5	0.96 (2)	C20—C21	1.352 (3)
C6—C7	1.444 (3)	C20—H20	0.99 (3)
C7—C8	1.389 (3)	C21—C22	1.414 (3)
C7—C12	1.405 (3)	C21—H21	0.99 (3)
C8—C9	1.388 (3)	C22—C23	1.366 (3)
C8—H8	1.00 (2)	C22—C24	1.505 (3)
C9—C10	1.397 (3)	C23—H23	1.05 (2)
C9—C15	1.490 (2)	C24—H24A	0.96
C10—C11	1.373 (3)	C24—H24B	0.96
C10—H10	0.95 (3)	C24—H24C	0.96
C11—C12	1.382 (3)	C25—C26	1.518 (3)
C11—H11	0.96 (2)	C25—H25A	0.97
C12—N1	1.382 (2)	C25—H25B	0.97
C13—N1	1.442 (3)	C26—C27	1.483 (4)
C13—C14	1.501 (3)	C26—H26A	0.97
C13—H13A	0.97	C26—H26B	0.97
C13—H13B	0.97	C27—O1	1.448 (3)
C14—H14A	0.96	C27—H27A	0.97
C14—H14B	0.96	C27—H27B	0.97
C14—H14C	0.96	O1—H1	0.82
N1—C1—C2	129.3 (2)	C17—C16—C25	120.02 (17)
N1—C1—C6	109.41 (17)	C15—C16—C25	122.67 (17)
C2—C1—C6	121.3 (2)	C16—C17—C18	121.29 (16)
C3—C2—C1	117.8 (2)	C16—C17—H17	120.7 (13)
C3—C2—H2	123.9 (15)	C18—C17—H17	117.9 (13)
C1—C2—H2	118.2 (15)	C19—C18—C17	117.25 (16)
C2—C3—C4	122.1 (2)	C19—C18—C23	119.47 (16)
C2—C3—H3	118.3 (19)	C17—C18—C23	123.28 (16)
C4—C3—H3	119.6 (19)	N2—C19—C18	122.06 (15)
C5—C4—C3	120.5 (2)	N2—C19—C20	119.33 (16)
C5—C4—H4	119.5 (17)	C18—C19—C20	118.59 (17)
C3—C4—H4	119.7 (17)	C21—C20—C19	120.50 (19)
C4—C5—C6	118.9 (2)	C21—C20—H20	118.1 (16)
C4—C5—H5	119.3 (14)	C19—C20—H20	121.2 (16)
C6—C5—H5	121.7 (14)	C20—C21—C22	121.63 (19)
C5—C6—C1	119.39 (19)	C20—C21—H21	119.3 (16)
C5—C6—C7	134.31 (19)	C22—C21—H21	118.6 (16)
C1—C6—C7	106.28 (17)	C23—C22—C21	118.70 (18)
C8—C7—C12	119.11 (17)	C23—C22—C24	121.7 (2)
C8—C7—C6	134.49 (17)	C21—C22—C24	119.60 (19)
C12—C7—C6	106.33 (16)	C22—C23—C18	121.07 (18)
C9—C8—C7	119.75 (16)	C22—C23—H23	119.2 (13)
C9—C8—H8	119.4 (14)	C18—C23—H23	119.7 (13)
C7—C8—H8	120.8 (14)	C22—C24—H24A	109.5
C8—C9—C10	119.14 (17)	C22—C24—H24B	109.5
C8—C9—C15	119.86 (15)	H24A—C24—H24B	109.5
C10—C9—C15	120.91 (16)	C22—C24—H24C	109.5
C11—C10—C9	122.51 (18)	H24A—C24—H24C	109.5
C11—C10—H10	116.8 (15)	H24B—C24—H24C	109.5
C9—C10—H10	120.7 (15)	C16—C25—C26	117.85 (18)
C10—C11—C12	117.50 (17)	C16—C25—H25A	107.8
C10—C11—H11	122.1 (14)	C26—C25—H25A	107.8
C12—C11—H11	120.4 (14)	C16—C25—H25B	107.8
C11—C12—N1	128.64 (18)	C26—C25—H25B	107.8
C11—C12—C7	121.90 (17)	H25A—C25—H25B	107.2
N1—C12—C7	109.45 (17)	C27—C26—C25	115.1 (2)
N1—C13—C14	113.27 (19)	C27—C26—H26A	108.5
N1—C13—H13A	108.9	C25—C26—H26A	108.5
C14—C13—H13A	108.9	C27—C26—H26B	108.5
N1—C13—H13B	108.9	C25—C26—H26B	108.5
C14—C13—H13B	108.9	H26A—C26—H26B	107.5
H13A—C13—H13B	107.7	O1—C27—C26	109.2 (2)
C13—C14—H14A	109.5	O1—C27—H27A	109.8
C13—C14—H14B	109.5	C26—C27—H27A	109.8
H14A—C14—H14B	109.5	O1—C27—H27B	109.8
C13—C14—H14C	109.5	C26—C27—H27B	109.8
H14A—C14—H14C	109.5	H27A—C27—H27B	108.3
H14B—C14—H14C	109.5	C1—N1—C12	108.52 (16)
N2—C15—C16	123.25 (16)	C1—N1—C13	126.70 (18)
N2—C15—C9	114.92 (15)	C12—N1—C13	124.74 (18)
C16—C15—C9	121.83 (15)	C15—N2—C19	118.85 (15)
C17—C16—C15	117.26 (15)	C27—O1—H1	109.5
N1—C1—C2—C3	178.2 (2)	C15—C16—C17—C18	−2.1 (2)
C6—C1—C2—C3	−0.1 (3)	C25—C16—C17—C18	−179.67 (16)
C1—C2—C3—C4	1.0 (4)	C16—C17—C18—C19	2.3 (3)
C2—C3—C4—C5	−0.9 (4)	C16—C17—C18—C23	−177.00 (16)
C3—C4—C5—C6	0.0 (4)	C17—C18—C19—N2	−0.8 (3)
C4—C5—C6—C1	0.8 (3)	C23—C18—C19—N2	178.51 (16)
C4—C5—C6—C7	−176.9 (2)	C17—C18—C19—C20	−179.44 (17)
N1—C1—C6—C5	−179.39 (17)	C23—C18—C19—C20	−0.1 (3)
C2—C1—C6—C5	−0.8 (3)	N2—C19—C20—C21	−177.61 (19)
N1—C1—C6—C7	−1.1 (2)	C18—C19—C20—C21	1.0 (3)
C2—C1—C6—C7	177.49 (17)	C19—C20—C21—C22	−0.3 (3)
C5—C6—C7—C8	1.8 (4)	C20—C21—C22—C23	−1.4 (3)
C1—C6—C7—C8	−176.15 (19)	C20—C21—C22—C24	178.5 (2)
C5—C6—C7—C12	178.6 (2)	C21—C22—C23—C18	2.3 (3)
C1—C6—C7—C12	0.70 (19)	C24—C22—C23—C18	−177.59 (18)
C12—C7—C8—C9	−1.7 (3)	C19—C18—C23—C22	−1.6 (3)
C6—C7—C8—C9	174.82 (18)	C17—C18—C23—C22	177.69 (17)
C7—C8—C9—C10	3.4 (3)	C17—C16—C25—C26	−92.1 (2)
C7—C8—C9—C15	179.91 (15)	C15—C16—C25—C26	90.4 (2)
C8—C9—C10—C11	−2.1 (3)	C16—C25—C26—C27	61.1 (3)
C15—C9—C10—C11	−178.59 (18)	C25—C26—C27—O1	−177.84 (19)
C9—C10—C11—C12	−0.9 (3)	C2—C1—N1—C12	−177.38 (19)
C10—C11—C12—N1	−175.81 (18)	C6—C1—N1—C12	1.0 (2)
C10—C11—C12—C7	2.6 (3)	C2—C1—N1—C13	4.8 (3)
C8—C7—C12—C11	−1.3 (3)	C6—C1—N1—C13	−176.76 (18)
C6—C7—C12—C11	−178.78 (17)	C11—C12—N1—C1	177.99 (19)
C8—C7—C12—N1	177.34 (15)	C7—C12—N1—C1	−0.6 (2)
C6—C7—C12—N1	−0.09 (19)	C11—C12—N1—C13	−4.2 (3)
C8—C9—C15—N2	−62.5 (2)	C7—C12—N1—C13	177.27 (17)
C10—C9—C15—N2	113.96 (19)	C14—C13—N1—C1	95.3 (3)
C8—C9—C15—C16	116.72 (19)	C14—C13—N1—C12	−82.2 (3)
C10—C9—C15—C16	−66.8 (2)	C16—C15—N2—C19	1.1 (3)
N2—C15—C16—C17	0.3 (3)	C9—C15—N2—C19	−179.70 (15)
C9—C15—C16—C17	−178.81 (15)	C18—C19—N2—C15	−0.8 (3)
N2—C15—C16—C25	177.89 (16)	C20—C19—N2—C15	177.79 (17)
C9—C15—C16—C25	−1.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2i	0.82	2.18	2.987 (2)	166
C17—H17···O1ii	0.97 (2)	2.38 (2)	3.334 (3)	171 (2)
C10—H10···Cg1i	0.96 (3)	2.76 (2)	3.559 (2)	141 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2i	0.82	2.18	2.987 (2)	166
C17—H17⋯O1ii	0.97 (2)	2.38 (2)	3.334 (3)	171 (2)
C10—H10⋯Cg1i	0.96 (3)	2.76 (2)	3.559 (2)	141 (2)

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the N2/C15–C19 ring.