3-[4-(10H-Indolo[3,2-b]quinolin-11-yl)piperazin-1-yl]propan-1-ol.

In the title compound, C(22)H(24)N(4)O, the aromatic moiety is essentially planar (r.m.s. deviation of a least-squares plane fitted through all non-H atoms = 0.0386 Å) and is rotated by 89.98 (4)° from the piperazine ring, which adopts the expected chair conformation. The propanol chain is not fully extended away from the piperazine ring. In the crystal, there are two unique hydrogen-bonding inter-actions. One is an O-H⋯N inter-action which, together with an inversion-related symmetry equivalent, forms a ring motif. The second is an N-H⋯N inter-action which links adjacent mol-ecules by means of a chain motif which propagates in the c-axis direction. Overall, a two-dimensional hydrogen-bonded structure is formed.

Related literature

For background information on the synthesis and properties of quindolines, see: Guyen et al. (2004 ▶); Ou et al. (2007 ▶). For synthesis details, see: Bierer et al. (1998 ▶); Takeuchi et al. (1997 ▶). For the graph-set notation description of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C22H24N4O

M = 360.45

Monoclinic,

a = 11.218 (2) Å

b = 15.673 (3) Å

c = 11.847 (2) Å

β = 117.417 (2)°

V = 1849.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.51 × 0.36 × 0.25 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.929, T max = 0.980

9503 measured reflections

3446 independent reflections

2678 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.03

3446 reflections

340 parameters

All H-atom parameters refined

Δρmax = 0.27 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811050215/fj2477sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811050215/fj2477Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050215/fj2477Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811050215/fj2477Isup4.cml

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

C22H24N4O	F(000) = 768
Mr = 360.45	Dx = 1.295 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3837 reflections
a = 11.218 (2) Å	θ = 2.3–28.0°
b = 15.673 (3) Å	µ = 0.08 mm−1
c = 11.847 (2) Å	T = 120 K
β = 117.417 (2)°	Prism, dark brown
V = 1849.0 (6) Å3	0.51 × 0.36 × 0.25 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	3446 independent reflections
Radiation source: sealed tube	2678 reflections with I > 2σ(I)
graphite	Rint = 0.027
thin–slice ω scans	θmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→13
Tmin = 0.929, Tmax = 0.980	k = −18→18
9503 measured reflections	l = −14→9

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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F2) = 0.108	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0523P)2 + 0.7097P] where P = (Fo2 + 2Fc2)/3
3446 reflections	(Δ/σ)max < 0.001
340 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.22 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
O	1.06789 (12)	0.50790 (7)	0.41013 (11)	0.0267 (3)
H1O	1.109 (2)	0.5355 (16)	0.493 (2)	0.068 (8)*
N1	0.37444 (13)	0.24064 (9)	0.40400 (13)	0.0220 (3)
H1N	0.3956 (18)	0.2294 (11)	0.3422 (18)	0.028 (5)*
N2	0.42965 (13)	0.31976 (8)	0.70450 (12)	0.0208 (3)
N3	0.61399 (13)	0.34403 (8)	0.45703 (12)	0.0209 (3)
N4	0.79071 (12)	0.39539 (8)	0.35679 (12)	0.0210 (3)
C1	0.55854 (15)	0.33858 (10)	0.54422 (15)	0.0198 (3)
C2	0.44663 (15)	0.28845 (10)	0.51126 (15)	0.0198 (3)
C3	0.26853 (15)	0.20239 (10)	0.41345 (15)	0.0207 (3)
C4	0.16905 (16)	0.14933 (10)	0.32651 (16)	0.0227 (4)
H4	0.1712 (16)	0.1326 (11)	0.2482 (17)	0.024 (4)*
C5	0.06949 (16)	0.12188 (11)	0.35618 (16)	0.0242 (4)
H5	0.0003 (18)	0.0838 (12)	0.2954 (17)	0.028 (5)*
C6	0.06798 (16)	0.14638 (11)	0.46923 (16)	0.0239 (4)
H6	−0.0062 (17)	0.1263 (11)	0.4887 (16)	0.027 (5)*
C7	0.16832 (16)	0.19778 (10)	0.55680 (16)	0.0221 (4)
H7	0.1694 (16)	0.2136 (10)	0.6364 (16)	0.020 (4)*
C8	0.26991 (15)	0.22583 (10)	0.52887 (15)	0.0199 (3)
C9	0.38517 (15)	0.28109 (10)	0.59321 (15)	0.0193 (3)
C10	0.54068 (15)	0.37040 (10)	0.74025 (15)	0.0202 (3)
C11	0.58953 (16)	0.41338 (11)	0.85823 (15)	0.0249 (4)
H11	0.5411 (16)	0.4042 (10)	0.9084 (15)	0.016 (4)*
C12	0.69713 (17)	0.46688 (11)	0.89926 (16)	0.0275 (4)
H12	0.7267 (16)	0.4987 (11)	0.9796 (17)	0.023 (4)*
C13	0.76274 (17)	0.47893 (11)	0.82389 (17)	0.0264 (4)
H13	0.839 (2)	0.5184 (13)	0.8534 (19)	0.038 (5)*
C14	0.72030 (16)	0.43782 (10)	0.70995 (16)	0.0226 (4)
H14	0.7664 (17)	0.4464 (11)	0.6598 (16)	0.026 (5)*
C15	0.60766 (15)	0.38205 (10)	0.66306 (15)	0.0199 (3)
C16	0.60048 (17)	0.42857 (11)	0.39894 (16)	0.0240 (4)
H16A	0.6495 (17)	0.4746 (11)	0.4637 (16)	0.023 (4)*
H16B	0.5062 (19)	0.4439 (11)	0.3571 (17)	0.028 (5)*
C17	0.65126 (16)	0.42647 (12)	0.30064 (16)	0.0244 (4)
H17A	0.6487 (17)	0.4852 (12)	0.2682 (16)	0.025 (5)*
H17B	0.5923 (17)	0.3887 (11)	0.2266 (16)	0.024 (4)*
C18	0.79162 (17)	0.30740 (10)	0.39967 (17)	0.0237 (4)
H18B	0.8840 (17)	0.2845 (11)	0.4334 (16)	0.021 (4)*
H18A	0.7292 (19)	0.2708 (12)	0.3271 (18)	0.034 (5)*
C19	0.74808 (17)	0.30570 (11)	0.50322 (16)	0.0231 (4)
H19A	0.8171 (18)	0.3353 (11)	0.5797 (17)	0.028 (5)*
H19B	0.7437 (17)	0.2446 (12)	0.5249 (16)	0.023 (4)*
C20	0.83818 (17)	0.40109 (11)	0.26025 (16)	0.0251 (4)
H20A	0.7803 (17)	0.3667 (11)	0.1848 (17)	0.023 (4)*
H20B	0.8255 (16)	0.4632 (11)	0.2318 (15)	0.017 (4)*
C21	0.98381 (17)	0.37398 (11)	0.30578 (17)	0.0274 (4)
H21A	1.0040 (17)	0.3868 (12)	0.2342 (17)	0.030 (5)*
H21B	0.9945 (17)	0.3105 (12)	0.3171 (17)	0.029 (5)*
C22	1.08386 (17)	0.41778 (11)	0.42631 (17)	0.0266 (4)
H22A	1.1778 (18)	0.4023 (11)	0.4449 (16)	0.024 (4)*
H22B	1.0721 (16)	0.3979 (11)	0.5050 (16)	0.023 (4)*

	U11	U22	U33	U12	U13	U23
O	0.0287 (6)	0.0227 (6)	0.0286 (7)	−0.0009 (5)	0.0130 (5)	0.0010 (5)
N1	0.0230 (7)	0.0257 (8)	0.0216 (7)	−0.0035 (6)	0.0140 (6)	−0.0041 (6)
N2	0.0214 (7)	0.0218 (7)	0.0204 (7)	0.0013 (5)	0.0105 (6)	0.0006 (6)
N3	0.0204 (7)	0.0222 (7)	0.0239 (7)	0.0000 (5)	0.0135 (6)	0.0012 (6)
N4	0.0209 (7)	0.0208 (7)	0.0244 (7)	0.0006 (5)	0.0131 (6)	0.0014 (5)
C1	0.0193 (8)	0.0200 (8)	0.0213 (8)	0.0031 (6)	0.0104 (6)	0.0024 (6)
C2	0.0200 (8)	0.0198 (8)	0.0195 (8)	0.0021 (6)	0.0091 (7)	−0.0004 (6)
C3	0.0194 (8)	0.0198 (8)	0.0237 (8)	0.0014 (6)	0.0106 (7)	0.0019 (6)
C4	0.0242 (8)	0.0222 (8)	0.0216 (8)	0.0006 (7)	0.0106 (7)	−0.0010 (7)
C5	0.0199 (8)	0.0212 (8)	0.0275 (9)	−0.0010 (7)	0.0074 (7)	0.0011 (7)
C6	0.0196 (8)	0.0234 (9)	0.0305 (9)	0.0000 (7)	0.0131 (7)	0.0030 (7)
C7	0.0222 (8)	0.0225 (9)	0.0232 (8)	0.0012 (6)	0.0118 (7)	0.0017 (7)
C8	0.0201 (8)	0.0188 (8)	0.0213 (8)	0.0020 (6)	0.0099 (7)	0.0017 (6)
C9	0.0197 (8)	0.0186 (8)	0.0210 (8)	0.0020 (6)	0.0105 (7)	0.0010 (6)
C10	0.0191 (8)	0.0181 (8)	0.0226 (8)	0.0031 (6)	0.0089 (7)	0.0019 (6)
C11	0.0252 (8)	0.0268 (9)	0.0243 (9)	0.0009 (7)	0.0127 (7)	−0.0005 (7)
C12	0.0273 (9)	0.0281 (9)	0.0239 (9)	−0.0009 (7)	0.0090 (7)	−0.0067 (7)
C13	0.0208 (8)	0.0259 (9)	0.0297 (9)	−0.0020 (7)	0.0092 (7)	−0.0034 (7)
C14	0.0194 (8)	0.0221 (9)	0.0271 (9)	0.0018 (6)	0.0115 (7)	0.0003 (7)
C15	0.0184 (8)	0.0183 (8)	0.0228 (8)	0.0042 (6)	0.0093 (7)	0.0024 (6)
C16	0.0204 (8)	0.0255 (9)	0.0266 (9)	0.0041 (7)	0.0113 (7)	0.0056 (7)
C17	0.0233 (9)	0.0271 (9)	0.0243 (9)	0.0012 (7)	0.0122 (7)	0.0049 (7)
C18	0.0255 (9)	0.0199 (8)	0.0314 (9)	−0.0002 (7)	0.0178 (8)	−0.0014 (7)
C19	0.0240 (8)	0.0193 (9)	0.0304 (9)	0.0032 (7)	0.0164 (8)	0.0040 (7)
C20	0.0295 (9)	0.0270 (10)	0.0235 (9)	−0.0034 (7)	0.0162 (8)	−0.0020 (7)
C21	0.0331 (10)	0.0247 (9)	0.0341 (10)	−0.0005 (7)	0.0239 (8)	−0.0013 (8)
C22	0.0260 (9)	0.0223 (9)	0.0357 (10)	0.0026 (7)	0.0178 (8)	0.0052 (7)

O—H1O	0.97 (3)	C10—C15	1.438 (2)
O—C22	1.426 (2)	C11—H11	0.984 (16)
N1—H1N	0.885 (19)	C11—C12	1.362 (2)
N1—C2	1.373 (2)	C12—H12	0.987 (18)
N1—C3	1.381 (2)	C12—C13	1.407 (2)
N2—C9	1.322 (2)	C13—H13	0.98 (2)
N2—C10	1.369 (2)	C13—C14	1.368 (2)
N3—C1	1.433 (2)	C14—H14	0.960 (18)
N3—C16	1.468 (2)	C14—C15	1.422 (2)
N3—C19	1.471 (2)	C16—H16A	1.011 (18)
N4—C17	1.473 (2)	C16—H16B	0.969 (19)
N4—C18	1.468 (2)	C16—C17	1.514 (2)
N4—C20	1.470 (2)	C17—H17A	0.992 (18)
C1—C2	1.376 (2)	C17—H17B	1.011 (17)
C1—C15	1.427 (2)	C18—H18B	0.991 (17)
C2—C9	1.431 (2)	C18—H18A	1.00 (2)
C3—C4	1.393 (2)	C18—C19	1.515 (2)
C3—C8	1.409 (2)	C19—H19A	0.995 (18)
C4—H4	0.976 (17)	C19—H19B	0.999 (18)
C4—C5	1.385 (2)	C20—H20A	0.988 (18)
C5—H5	0.981 (18)	C20—H20B	1.019 (17)
C5—C6	1.401 (2)	C20—C21	1.526 (2)
C6—H6	1.011 (18)	C21—H21A	0.994 (19)
C6—C7	1.385 (2)	C21—H21B	1.004 (19)
C7—H7	0.969 (17)	C21—C22	1.515 (2)
C7—C8	1.396 (2)	C22—H22A	1.002 (18)
C8—C9	1.448 (2)	C22—H22B	1.048 (17)
C10—C11	1.415 (2)
H1O—O—C22	109.5 (14)	H13—C13—C14	120.0 (12)
H1N—N1—C2	127.3 (12)	C13—C14—H14	120.2 (11)
H1N—N1—C3	123.3 (12)	C13—C14—C15	121.17 (16)
C2—N1—C3	108.97 (13)	H14—C14—C15	118.6 (10)
C9—N2—C10	116.48 (13)	C1—C15—C10	119.30 (14)
C1—N3—C16	113.97 (12)	C1—C15—C14	123.29 (14)
C1—N3—C19	114.61 (12)	C10—C15—C14	117.40 (14)
C16—N3—C19	114.20 (12)	N3—C16—H16A	112.7 (10)
C17—N4—C18	107.68 (13)	N3—C16—H16B	108.4 (11)
C17—N4—C20	108.57 (12)	N3—C16—C17	110.28 (14)
C18—N4—C20	112.26 (13)	H16A—C16—H16B	107.2 (14)
N3—C1—C2	118.14 (14)	H16A—C16—C17	109.4 (10)
N3—C1—C15	125.75 (14)	H16B—C16—C17	108.7 (10)
C2—C1—C15	116.10 (14)	N4—C17—C16	110.94 (13)
N1—C2—C1	130.28 (15)	N4—C17—H17A	108.5 (10)
N1—C2—C9	108.71 (13)	N4—C17—H17B	109.4 (9)
C1—C2—C9	121.00 (14)	C16—C17—H17A	108.9 (10)
N1—C3—C4	128.75 (15)	C16—C17—H17B	110.6 (10)
N1—C3—C8	109.88 (14)	H17A—C17—H17B	108.4 (14)
C4—C3—C8	121.36 (15)	N4—C18—H18B	108.6 (10)
C3—C4—H4	120.1 (10)	N4—C18—H18A	110.5 (11)
C3—C4—C5	117.59 (15)	N4—C18—C19	110.06 (13)
H4—C4—C5	122.3 (10)	H18B—C18—H18A	109.1 (14)
C4—C5—H5	117.4 (10)	H18B—C18—C19	109.5 (10)
C4—C5—C6	121.58 (15)	H18A—C18—C19	109.0 (11)
H5—C5—C6	121.0 (10)	N3—C19—C18	110.32 (14)
C5—C6—H6	120.4 (10)	N3—C19—H19A	112.5 (10)
C5—C6—C7	120.82 (15)	N3—C19—H19B	108.9 (10)
H6—C6—C7	118.7 (10)	C18—C19—H19A	108.9 (10)
C6—C7—H7	121.3 (10)	C18—C19—H19B	107.3 (10)
C6—C7—C8	118.45 (15)	H19A—C19—H19B	108.8 (14)
H7—C7—C8	120.3 (10)	N4—C20—H20A	110.4 (10)
C3—C8—C7	120.17 (14)	N4—C20—H20B	105.7 (9)
C3—C8—C9	105.96 (13)	N4—C20—C21	114.87 (14)
C7—C8—C9	133.82 (15)	H20A—C20—H20B	106.8 (13)
N2—C9—C2	124.13 (14)	H20A—C20—C21	108.6 (10)
N2—C9—C8	129.39 (14)	H20B—C20—C21	110.3 (9)
C2—C9—C8	106.48 (13)	C20—C21—H21A	105.6 (10)
N2—C10—C11	117.70 (14)	C20—C21—H21B	111.4 (10)
N2—C10—C15	122.98 (14)	C20—C21—C22	114.52 (14)
C11—C10—C15	119.32 (14)	H21A—C21—H21B	104.8 (14)
C10—C11—H11	117.2 (9)	H21A—C21—C22	110.6 (10)
C10—C11—C12	121.46 (16)	H21B—C21—C22	109.4 (10)
H11—C11—C12	121.3 (9)	O—C22—C21	109.25 (14)
C11—C12—H12	120.3 (10)	O—C22—H22A	108.9 (10)
C11—C12—C13	119.52 (16)	O—C22—H22B	110.8 (9)
H12—C12—C13	120.1 (10)	C21—C22—H22A	110.2 (10)
C12—C13—H13	118.9 (12)	C21—C22—H22B	111.2 (9)
C12—C13—C14	121.11 (16)	H22A—C22—H22B	106.4 (13)
C16—N3—C1—C2	112.37 (16)	C7—C8—C9—C2	−176.76 (17)
C16—N3—C1—C15	−66.45 (19)	C9—N2—C10—C11	179.26 (14)
C19—N3—C1—C2	−113.44 (16)	C9—N2—C10—C15	−0.1 (2)
C19—N3—C1—C15	67.74 (19)	N2—C10—C11—C12	−178.11 (15)
C3—N1—C2—C1	−178.98 (16)	C15—C10—C11—C12	1.3 (2)
C3—N1—C2—C9	−0.12 (17)	C10—C11—C12—C13	−1.0 (3)
N3—C1—C2—N1	−0.4 (2)	C11—C12—C13—C14	0.0 (3)
N3—C1—C2—C9	−179.17 (13)	C12—C13—C14—C15	0.6 (3)
C15—C1—C2—N1	178.51 (15)	C13—C14—C15—C1	179.20 (15)
C15—C1—C2—C9	−0.2 (2)	C13—C14—C15—C10	−0.2 (2)
C2—N1—C3—C4	179.23 (16)	N3—C1—C15—C10	179.73 (14)
C2—N1—C3—C8	0.45 (18)	N3—C1—C15—C14	0.3 (2)
N1—C3—C4—C5	−177.20 (15)	C2—C1—C15—C10	0.9 (2)
C8—C3—C4—C5	1.5 (2)	C2—C1—C15—C14	−178.53 (14)
C3—C4—C5—C6	0.1 (2)	N2—C10—C15—C1	−0.8 (2)
C4—C5—C6—C7	−1.4 (2)	N2—C10—C15—C14	178.69 (14)
C5—C6—C7—C8	1.1 (2)	C11—C10—C15—C1	179.88 (14)
C6—C7—C8—C3	0.5 (2)	C11—C10—C15—C14	−0.7 (2)
C6—C7—C8—C9	177.43 (16)	C1—N3—C16—C17	−175.37 (13)
N1—C3—C8—C7	177.12 (14)	C19—N3—C16—C17	50.25 (18)
N1—C3—C8—C9	−0.60 (17)	C18—N4—C17—C16	62.64 (17)
C4—C3—C8—C7	−1.8 (2)	C20—N4—C17—C16	−175.58 (14)
C4—C3—C8—C9	−179.48 (14)	N3—C16—C17—N4	−55.76 (18)
C10—N2—C9—C2	0.8 (2)	C17—N4—C18—C19	−63.16 (17)
C10—N2—C9—C8	−178.45 (15)	C20—N4—C18—C19	177.38 (13)
N1—C2—C9—N2	−179.67 (14)	C1—N3—C19—C18	174.66 (13)
N1—C2—C9—C8	−0.25 (17)	C16—N3—C19—C18	−51.25 (18)
C1—C2—C9—N2	−0.7 (2)	N4—C18—C19—N3	57.42 (18)
C1—C2—C9—C8	178.74 (14)	C17—N4—C20—C21	177.89 (14)
C3—C8—C9—N2	179.89 (15)	C18—N4—C20—C21	−63.17 (18)
C3—C8—C9—C2	0.51 (17)	N4—C20—C21—C22	−52.4 (2)
C7—C8—C9—N2	2.6 (3)	C20—C21—C22—O	−53.75 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O—H1O···N4i	0.97 (3)	1.94 (3)	2.8990 (18)	169 (2)
N1—H1N···N2ii	0.885 (19)	1.99 (2)	2.866 (2)	168.4 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O—H1O⋯N4i	0.97 (3)	1.94 (3)	2.8990 (18)	169 (2)
N1—H1N⋯N2ii	0.885 (19)	1.99 (2)	2.866 (2)	168.4 (17)

Symmetry codes: (i) ; (ii) .