4-(8-Eth-oxy-2,3-dihydro-1H-cyclo-penta-[c]quinolin-4-yl)butane-1-peroxol.

In the title mol-ecule, C(18)H(23)NO(3), the hydro-per-oxy-butyl substituent is nearly fully extended, with the four torsion angles in the range 170.23 (10)-178.71 (9)°. The O-O distance in the hydro-peroxide group is 1.4690 (13) Å. This group acts as an inter-molecular hydrogen-bond donor to a quinoline N atom. This results in dimeric units about the respective inversion centers, with graph-set notation R(2) (2)(18).

Related literature

For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For graph-set motifs, see: Etter (1990 ▶). For the biological activity of dihydro­quinolines, see: Babiak et al. (1999 ▶); Cracknell et al. (1998 ▶); Dillard et al. (1973 ▶); Fotie et al. (2010 ▶); Lockhart et al. (2001 ▶); Shah et al. (2005 ▶); Takahashi et al. (2006 ▶); Thorisson et al. (1992 ▶). For related structures, see: Grignon-Dubois et al. (1993 ▶); Noland et al. (1996 ▶).

Experimental

Crystal data

C18H23NO3

M = 301.37

Triclinic,

a = 8.0113 (2) Å

b = 8.5091 (2) Å

c = 12.6334 (3) Å

α = 73.605 (1)°

β = 74.936 (1)°

γ = 78.136 (1)°

V = 789.63 (3) Å3

Z = 2

Cu Kα radiation

μ = 0.69 mm−1

T = 90 K

0.19 × 0.17 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.880, T max = 0.904

9369 measured reflections

2798 independent reflections

2400 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.110

S = 1.08

2798 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021781/fj2311sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021781/fj2311Isup2.hkl

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

C18H23NO3	Z = 2
Mr = 301.37	F(000) = 324
Triclinic, P1	Dx = 1.268 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 8.0113 (2) Å	Cell parameters from 4518 reflections
b = 8.5091 (2) Å	θ = 3.7–68.3°
c = 12.6334 (3) Å	µ = 0.69 mm−1
α = 73.605 (1)°	T = 90 K
β = 74.936 (1)°	Prism, colourless
γ = 78.136 (1)°	0.19 × 0.17 × 0.15 mm
V = 789.63 (3) Å3

Bruker APEXII CCD diffractometer	2798 independent reflections
Radiation source: fine-focus sealed tube	2400 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 68.8°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
Tmin = 0.880, Tmax = 0.904	k = −9→10
9369 measured reflections	l = −15→15

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0626P)2 + 0.1754P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2798 reflections	Δρmax = 0.22 e Å−3
202 parameters	Δρmin = −0.27 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (7)

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	0.54940 (12)	0.44045 (11)	1.21141 (7)	0.0202 (2)
O2	0.43514 (12)	0.35072 (12)	1.31138 (8)	0.0233 (3)
H2	0.3429	0.4140	1.3292	0.035*
O3	0.98882 (12)	0.17854 (11)	0.27498 (8)	0.0201 (2)
N1	0.84064 (14)	0.40032 (13)	0.66551 (9)	0.0180 (3)
C1	0.96537 (17)	0.22269 (16)	0.37459 (11)	0.0177 (3)
C2	1.08402 (17)	0.17863 (16)	0.44285 (11)	0.0175 (3)
H2A	1.1914	0.1104	0.4233	0.021*
C3	1.04475 (17)	0.23589 (15)	0.54275 (11)	0.0166 (3)
C4	0.88489 (17)	0.33756 (16)	0.57160 (11)	0.0171 (3)
C5	0.76525 (17)	0.37924 (16)	0.49902 (11)	0.0184 (3)
H5	0.6573	0.4473	0.5172	0.022*
C6	0.80419 (17)	0.32234 (16)	0.40359 (11)	0.0198 (3)
H6	0.7225	0.3498	0.3562	0.024*
C7	1.15889 (17)	0.19861 (16)	0.61825 (11)	0.0173 (3)
C8	1.33845 (17)	0.09920 (17)	0.60806 (11)	0.0203 (3)
H8A	1.4123	0.1362	0.5321	0.024*
H8B	1.3323	−0.0203	0.6226	0.024*
C9	1.40947 (18)	0.13488 (18)	0.69997 (12)	0.0235 (3)
H9A	1.4726	0.0323	0.7404	0.028*
H9B	1.4909	0.2177	0.6656	0.028*
C10	1.25038 (18)	0.20199 (18)	0.78213 (12)	0.0229 (3)
H10A	1.2155	0.1143	0.8507	0.027*
H10B	1.2753	0.2956	0.8047	0.027*
C11	1.11048 (17)	0.25808 (16)	0.71348 (11)	0.0188 (3)
C12	0.95014 (17)	0.36144 (16)	0.73497 (11)	0.0184 (3)
C13	0.89624 (18)	0.43704 (17)	0.83518 (11)	0.0209 (3)
H13A	0.8268	0.5471	0.8139	0.025*
H13B	1.0025	0.4540	0.8543	0.025*
C14	0.78889 (17)	0.33287 (16)	0.94029 (11)	0.0186 (3)
H14A	0.6851	0.3105	0.9213	0.022*
H14B	0.8601	0.2254	0.9657	0.022*
C15	0.73048 (17)	0.42275 (16)	1.03551 (11)	0.0190 (3)
H15A	0.8351	0.4403	1.0561	0.023*
H15B	0.6655	0.5329	1.0079	0.023*
C16	0.61601 (18)	0.32967 (16)	1.13985 (11)	0.0194 (3)
H16A	0.5194	0.2962	1.1196	0.023*
H16B	0.6850	0.2291	1.1779	0.023*
C17	1.15683 (18)	0.09386 (16)	0.23380 (11)	0.0201 (3)
H17A	1.1735	−0.0203	0.2812	0.024*
H17B	1.2503	0.1526	0.2357	0.024*
C18	1.1631 (2)	0.09065 (18)	0.11403 (12)	0.0256 (3)
H18A	1.0682	0.0347	0.1132	0.038*
H18B	1.2755	0.0309	0.0835	0.038*
H18C	1.1496	0.2043	0.0676	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0200 (5)	0.0214 (5)	0.0171 (5)	−0.0013 (4)	0.0010 (4)	−0.0070 (4)
O2	0.0197 (5)	0.0255 (5)	0.0176 (5)	0.0011 (4)	0.0027 (4)	−0.0033 (4)
O3	0.0201 (5)	0.0229 (5)	0.0180 (5)	0.0001 (4)	−0.0048 (4)	−0.0076 (4)
N1	0.0179 (6)	0.0168 (6)	0.0179 (6)	−0.0021 (4)	−0.0017 (4)	−0.0044 (4)
C1	0.0208 (7)	0.0161 (7)	0.0153 (6)	−0.0040 (5)	−0.0026 (5)	−0.0027 (5)
C2	0.0164 (7)	0.0150 (6)	0.0183 (7)	−0.0013 (5)	−0.0018 (5)	−0.0023 (5)
C3	0.0171 (7)	0.0141 (6)	0.0166 (7)	−0.0038 (5)	−0.0023 (5)	−0.0006 (5)
C4	0.0181 (7)	0.0141 (6)	0.0168 (7)	−0.0033 (5)	−0.0004 (5)	−0.0022 (5)
C5	0.0151 (7)	0.0165 (7)	0.0210 (7)	0.0002 (5)	−0.0027 (5)	−0.0029 (5)
C6	0.0187 (7)	0.0193 (7)	0.0199 (7)	−0.0030 (5)	−0.0051 (5)	−0.0017 (5)
C7	0.0173 (7)	0.0148 (6)	0.0175 (7)	−0.0039 (5)	−0.0023 (5)	−0.0003 (5)
C8	0.0176 (7)	0.0211 (7)	0.0201 (7)	0.0016 (5)	−0.0045 (5)	−0.0045 (5)
C9	0.0183 (7)	0.0282 (8)	0.0235 (7)	−0.0008 (6)	−0.0065 (6)	−0.0056 (6)
C10	0.0222 (7)	0.0259 (8)	0.0219 (7)	−0.0011 (6)	−0.0075 (6)	−0.0071 (6)
C11	0.0194 (7)	0.0180 (7)	0.0175 (7)	−0.0052 (5)	−0.0029 (5)	−0.0012 (5)
C12	0.0193 (7)	0.0164 (7)	0.0182 (7)	−0.0043 (5)	−0.0017 (5)	−0.0032 (5)
C13	0.0215 (7)	0.0203 (7)	0.0212 (7)	−0.0037 (5)	−0.0020 (6)	−0.0075 (6)
C14	0.0194 (7)	0.0188 (7)	0.0182 (7)	−0.0005 (5)	−0.0043 (5)	−0.0067 (5)
C15	0.0181 (7)	0.0203 (7)	0.0192 (7)	−0.0006 (5)	−0.0041 (5)	−0.0072 (5)
C16	0.0213 (7)	0.0195 (7)	0.0179 (7)	0.0005 (5)	−0.0043 (5)	−0.0075 (5)
C17	0.0214 (7)	0.0180 (7)	0.0197 (7)	−0.0001 (5)	−0.0029 (5)	−0.0058 (5)
C18	0.0307 (8)	0.0246 (8)	0.0226 (7)	−0.0005 (6)	−0.0046 (6)	−0.0106 (6)

O1—C16	1.4193 (15)	C9—H9B	0.9900
O1—O2	1.4690 (13)	C10—C11	1.5125 (18)
O2—H2	0.8400	C10—H10A	0.9900
O3—C1	1.3693 (15)	C10—H10B	0.9900
O3—C17	1.4319 (16)	C11—C12	1.4094 (19)
N1—C12	1.3288 (17)	C12—C13	1.5048 (18)
N1—C4	1.3709 (17)	C13—C14	1.5310 (18)
C1—C2	1.3729 (18)	C13—H13A	0.9900
C1—C6	1.4142 (19)	C13—H13B	0.9900
C2—C3	1.4166 (18)	C14—C15	1.5266 (17)
C2—H2A	0.9500	C14—H14A	0.9900
C3—C4	1.4147 (18)	C14—H14B	0.9900
C3—C7	1.4176 (18)	C15—C16	1.5122 (18)
C4—C5	1.4208 (18)	C15—H15A	0.9900
C5—C6	1.3628 (19)	C15—H15B	0.9900
C5—H5	0.9500	C16—H16A	0.9900
C6—H6	0.9500	C16—H16B	0.9900
C7—C11	1.3691 (19)	C17—C18	1.5087 (18)
C7—C8	1.5054 (18)	C17—H17A	0.9900
C8—C9	1.5420 (19)	C17—H17B	0.9900
C8—H8A	0.9900	C18—H18A	0.9800
C8—H8B	0.9900	C18—H18B	0.9800
C9—C10	1.5413 (19)	C18—H18C	0.9800
C9—H9A	0.9900
C16—O1—O2	105.80 (9)	C7—C11—C12	120.33 (12)
O1—O2—H2	109.5	C7—C11—C10	111.14 (12)
C1—O3—C17	117.05 (10)	C12—C11—C10	128.50 (12)
C12—N1—C4	119.06 (11)	N1—C12—C11	121.27 (12)
O3—C1—C2	125.10 (12)	N1—C12—C13	116.62 (11)
O3—C1—C6	114.06 (11)	C11—C12—C13	122.09 (12)
C2—C1—C6	120.84 (12)	C12—C13—C14	114.07 (11)
C1—C2—C3	119.32 (12)	C12—C13—H13A	108.7
C1—C2—H2A	120.3	C14—C13—H13A	108.7
C3—C2—H2A	120.3	C12—C13—H13B	108.7
C4—C3—C2	120.22 (12)	C14—C13—H13B	108.7
C4—C3—C7	116.10 (12)	H13A—C13—H13B	107.6
C2—C3—C7	123.68 (12)	C15—C14—C13	110.73 (11)
N1—C4—C3	123.16 (12)	C15—C14—H14A	109.5
N1—C4—C5	118.20 (12)	C13—C14—H14A	109.5
C3—C4—C5	118.63 (12)	C15—C14—H14B	109.5
C6—C5—C4	120.53 (12)	C13—C14—H14B	109.5
C6—C5—H5	119.7	H14A—C14—H14B	108.1
C4—C5—H5	119.7	C16—C15—C14	113.20 (11)
C5—C6—C1	120.44 (12)	C16—C15—H15A	108.9
C5—C6—H6	119.8	C14—C15—H15A	108.9
C1—C6—H6	119.8	C16—C15—H15B	108.9
C11—C7—C3	120.02 (12)	C14—C15—H15B	108.9
C11—C7—C8	111.83 (11)	H15A—C15—H15B	107.8
C3—C7—C8	128.14 (12)	O1—C16—C15	106.06 (11)
C7—C8—C9	103.20 (11)	O1—C16—H16A	110.5
C7—C8—H8A	111.1	C15—C16—H16A	110.5
C9—C8—H8A	111.1	O1—C16—H16B	110.5
C7—C8—H8B	111.1	C15—C16—H16B	110.5
C9—C8—H8B	111.1	H16A—C16—H16B	108.7
H8A—C8—H8B	109.1	O3—C17—C18	107.10 (11)
C10—C9—C8	106.77 (11)	O3—C17—H17A	110.3
C10—C9—H9A	110.4	C18—C17—H17A	110.3
C8—C9—H9A	110.4	O3—C17—H17B	110.3
C10—C9—H9B	110.4	C18—C17—H17B	110.3
C8—C9—H9B	110.4	H17A—C17—H17B	108.6
H9A—C9—H9B	108.6	C17—C18—H18A	109.5
C11—C10—C9	103.12 (11)	C17—C18—H18B	109.5
C11—C10—H10A	111.1	H18A—C18—H18B	109.5
C9—C10—H10A	111.1	C17—C18—H18C	109.5
C11—C10—H10B	111.1	H18A—C18—H18C	109.5
C9—C10—H10B	111.1	H18B—C18—H18C	109.5
H10A—C10—H10B	109.1
C17—O3—C1—C2	−6.48 (18)	C3—C7—C8—C9	168.11 (13)
C17—O3—C1—C6	173.01 (11)	C7—C8—C9—C10	18.58 (14)
O3—C1—C2—C3	178.62 (11)	C8—C9—C10—C11	−19.42 (14)
C6—C1—C2—C3	−0.8 (2)	C3—C7—C11—C12	−2.3 (2)
C1—C2—C3—C4	−0.07 (19)	C8—C7—C11—C12	176.70 (12)
C1—C2—C3—C7	−179.45 (12)	C3—C7—C11—C10	179.39 (11)
C12—N1—C4—C3	−1.71 (19)	C8—C7—C11—C10	−1.59 (16)
C12—N1—C4—C5	179.37 (11)	C9—C10—C11—C7	13.27 (15)
C2—C3—C4—N1	−178.41 (11)	C9—C10—C11—C12	−164.84 (13)
C7—C3—C4—N1	1.02 (19)	C4—N1—C12—C11	0.34 (19)
C2—C3—C4—C5	0.51 (19)	C4—N1—C12—C13	178.70 (11)
C7—C3—C4—C5	179.94 (11)	C7—C11—C12—N1	1.7 (2)
N1—C4—C5—C6	178.92 (11)	C10—C11—C12—N1	179.63 (12)
C3—C4—C5—C6	−0.05 (19)	C7—C11—C12—C13	−176.59 (12)
C4—C5—C6—C1	−0.8 (2)	C10—C11—C12—C13	1.4 (2)
O3—C1—C6—C5	−178.21 (11)	N1—C12—C13—C14	89.79 (14)
C2—C1—C6—C5	1.3 (2)	C11—C12—C13—C14	−91.87 (15)
C4—C3—C7—C11	1.01 (19)	C12—C13—C14—C15	−176.62 (11)
C2—C3—C7—C11	−179.59 (12)	C13—C14—C15—C16	177.09 (10)
C4—C3—C7—C8	−177.84 (12)	O2—O1—C16—C15	178.71 (9)
C2—C3—C7—C8	1.6 (2)	C14—C15—C16—O1	−170.23 (10)
C11—C7—C8—C9	−10.82 (15)	C1—O3—C17—C18	−168.40 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1i	0.84	1.93	2.7466 (14)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1i	0.84	1.93	2.7466 (14)	165

Symmetry code: (i) .