11-(4-Methyl-phen-yl)-8,9-dihydro-7H-benzo[f]cyclo-penta-[b]quinolin-10(11H)-one.

In the title compound, C(23)H(19)NO, the naphthalene ring system and the cyclo-pent-2-enone ring exhibit planar conformations with maximum deviations of 0.034 (1) and 0.02 (1) Å, respectively. The 1,4-dihydro-pyridine ring adopts an envelope conformation with the C atom bearing the p-tolyl ring as the flap atom. Inter-molecular N-H⋯O hydrogen bonds and C-H⋯π inter-actions stabilize the crystal packing.

Related literature

For the medicinal use of quinoline and fused quinoline derivatives, see: Audisio et al. (2012 ▶); Kurasawa et al. (2012 ▶); Pokhrel et al. (2012 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C23H19NO

M = 325.39

Monoclinic,

a = 8.727 (1) Å

b = 11.6820 (14) Å

c = 16.240 (2) Å

β = 98.938 (5)°

V = 1635.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 113 K

0.24 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClearSM Expert; Rigaku/MSC, 2009 ▶) T min = 0.981, T max = 0.986

15928 measured reflections

3899 independent reflections

2991 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.124

S = 1.07

3899 reflections

231 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrystalClearSM Expert (Rigaku/MSC, 2009 ▶); cell refinement: CrystalClearSM Expert; data reduction: CrystalClearSM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812035659/hg5239sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035659/hg5239Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035659/hg5239Isup3.cml

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

C23H19NO	F(000) = 688
Mr = 325.39	Dx = 1.321 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 5530 reflections
a = 8.727 (1) Å	θ = 1.7–27.9°
b = 11.6820 (14) Å	µ = 0.08 mm−1
c = 16.240 (2) Å	T = 113 K
β = 98.938 (5)°	Prism, colorless
V = 1635.5 (3) Å3	0.24 × 0.20 × 0.18 mm
Z = 4

Rigaku Saturn724 CCD diffractometer	3899 independent reflections
Radiation source: rotating anode	2991 reflections with I > 2σ(I)
Multilayer monochromator	Rint = 0.031
Detector resolution: 14.222 pixels mm-1	θmax = 27.9°, θmin = 2.2°
ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClearSM Expert; Rigaku/MSC, 2009)	k = −15→15
Tmin = 0.981, Tmax = 0.986	l = −21→19
15928 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0777P)2 + 0.041P] where P = (Fo2 + 2Fc2)/3
3899 reflections	(Δ/σ)max < 0.001
231 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.32 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
O1	0.35410 (9)	0.68276 (7)	0.17550 (5)	0.0239 (2)
N1	0.67402 (12)	1.00971 (9)	0.20388 (6)	0.0210 (2)
C1	0.71537 (13)	1.01482 (10)	0.12380 (7)	0.0189 (3)
C2	0.67622 (12)	0.92753 (9)	0.06669 (7)	0.0181 (2)
C3	0.59399 (13)	0.81856 (9)	0.08934 (7)	0.0181 (3)
H3	0.5039	0.8036	0.0446	0.022*
C4	0.53334 (13)	0.83755 (10)	0.17008 (7)	0.0190 (3)
C5	0.57787 (13)	0.92659 (10)	0.22198 (7)	0.0198 (3)
C6	0.50911 (14)	0.92521 (10)	0.30110 (8)	0.0238 (3)
H6A	0.4506	0.9964	0.3075	0.029*
H6B	0.5903	0.9155	0.3504	0.029*
C7	0.40108 (14)	0.82132 (10)	0.28894 (8)	0.0227 (3)
H7A	0.4289	0.7654	0.3346	0.027*
H7B	0.2919	0.8451	0.2879	0.027*
C8	0.42339 (13)	0.76912 (10)	0.20551 (8)	0.0204 (3)
C9	0.79777 (13)	1.11263 (10)	0.10358 (8)	0.0216 (3)
H9	0.8258	1.1702	0.1445	0.026*
C10	0.83712 (13)	1.12502 (10)	0.02645 (8)	0.0229 (3)
H10	0.8904	1.1920	0.0134	0.027*
C11	0.79946 (13)	1.03903 (10)	−0.03478 (8)	0.0199 (3)
C12	0.72028 (13)	0.93887 (10)	−0.01424 (7)	0.0188 (2)
C13	0.69057 (13)	0.85257 (11)	−0.07591 (8)	0.0227 (3)
H13	0.6378	0.7849	−0.0639	0.027*
C14	0.73616 (14)	0.86444 (11)	−0.15246 (8)	0.0251 (3)
H14	0.7157	0.8048	−0.1925	0.030*
C15	0.81319 (14)	0.96438 (11)	−0.17238 (8)	0.0258 (3)
H15	0.8441	0.9724	−0.2257	0.031*
C16	0.84296 (13)	1.04920 (10)	−0.11474 (8)	0.0240 (3)
H16	0.8941	1.1167	−0.1285	0.029*
C17	0.70253 (13)	0.71503 (10)	0.09513 (7)	0.0183 (2)
C18	0.65617 (14)	0.61097 (10)	0.05873 (7)	0.0232 (3)
H18	0.5536	0.6029	0.0296	0.028*
C19	0.75686 (14)	0.51809 (11)	0.06393 (8)	0.0253 (3)
H19	0.7220	0.4476	0.0385	0.030*
C20	0.90795 (14)	0.52715 (10)	0.10585 (8)	0.0230 (3)
C21	0.95452 (14)	0.63162 (11)	0.14195 (8)	0.0239 (3)
H21	1.0576	0.6403	0.1702	0.029*
C22	0.85309 (14)	0.72368 (10)	0.13750 (8)	0.0218 (3)
H22	0.8872	0.7938	0.1639	0.026*
C23	1.01741 (15)	0.42637 (11)	0.11254 (9)	0.0319 (3)
H23A	1.1244	0.4540	0.1171	0.038*
H23B	0.9930	0.3783	0.0628	0.038*
H23C	1.0059	0.3813	0.1621	0.038*
H1	0.6867 (18)	1.0689 (14)	0.2399 (10)	0.045 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0220 (4)	0.0226 (5)	0.0270 (5)	−0.0030 (3)	0.0040 (4)	0.0034 (3)
N1	0.0233 (5)	0.0206 (5)	0.0197 (5)	−0.0025 (4)	0.0054 (4)	−0.0022 (4)
C1	0.0162 (5)	0.0199 (6)	0.0208 (6)	0.0016 (4)	0.0033 (5)	0.0012 (5)
C2	0.0160 (5)	0.0189 (6)	0.0192 (6)	0.0008 (4)	0.0023 (4)	0.0015 (4)
C3	0.0175 (5)	0.0181 (6)	0.0185 (6)	−0.0013 (4)	0.0024 (5)	0.0007 (4)
C4	0.0171 (5)	0.0194 (6)	0.0208 (6)	0.0011 (4)	0.0034 (5)	0.0026 (5)
C5	0.0175 (5)	0.0212 (6)	0.0208 (6)	0.0023 (4)	0.0033 (5)	0.0019 (5)
C6	0.0252 (6)	0.0265 (7)	0.0209 (7)	−0.0007 (5)	0.0075 (5)	0.0002 (5)
C7	0.0220 (6)	0.0233 (6)	0.0237 (7)	0.0015 (4)	0.0066 (5)	0.0044 (5)
C8	0.0176 (5)	0.0199 (6)	0.0232 (6)	0.0032 (4)	0.0019 (5)	0.0058 (5)
C9	0.0206 (6)	0.0179 (6)	0.0262 (7)	0.0000 (4)	0.0036 (5)	−0.0021 (5)
C10	0.0205 (6)	0.0177 (6)	0.0313 (7)	−0.0003 (4)	0.0071 (5)	0.0033 (5)
C11	0.0170 (5)	0.0198 (6)	0.0233 (6)	0.0030 (4)	0.0037 (5)	0.0044 (5)
C12	0.0162 (5)	0.0204 (6)	0.0196 (6)	0.0025 (4)	0.0023 (5)	0.0030 (4)
C13	0.0222 (6)	0.0237 (6)	0.0217 (6)	−0.0018 (5)	0.0015 (5)	0.0007 (5)
C14	0.0271 (6)	0.0273 (6)	0.0202 (6)	0.0007 (5)	0.0020 (5)	−0.0009 (5)
C15	0.0257 (6)	0.0310 (7)	0.0221 (7)	0.0059 (5)	0.0077 (5)	0.0059 (5)
C16	0.0232 (6)	0.0238 (6)	0.0264 (7)	0.0029 (5)	0.0086 (5)	0.0072 (5)
C17	0.0195 (5)	0.0201 (6)	0.0163 (6)	−0.0023 (4)	0.0060 (5)	0.0015 (4)
C18	0.0199 (6)	0.0244 (6)	0.0249 (7)	−0.0032 (5)	0.0020 (5)	−0.0024 (5)
C19	0.0270 (6)	0.0213 (6)	0.0284 (7)	−0.0025 (5)	0.0066 (5)	−0.0043 (5)
C20	0.0239 (6)	0.0240 (6)	0.0228 (6)	0.0016 (5)	0.0090 (5)	0.0013 (5)
C21	0.0189 (6)	0.0261 (6)	0.0261 (7)	−0.0015 (5)	0.0016 (5)	0.0030 (5)
C22	0.0225 (6)	0.0208 (6)	0.0222 (6)	−0.0029 (4)	0.0033 (5)	−0.0011 (5)
C23	0.0312 (7)	0.0278 (7)	0.0376 (8)	0.0055 (5)	0.0081 (6)	−0.0010 (6)

O1—C8	1.2366 (14)	C11—C16	1.4134 (17)
N1—C5	1.3454 (15)	C11—C12	1.4245 (15)
N1—C1	1.4039 (16)	C12—C13	1.4163 (17)
N1—H1	0.902 (17)	C13—C14	1.3700 (17)
C1—C2	1.3849 (16)	C13—H13	0.9500
C1—C9	1.4156 (15)	C14—C15	1.4097 (17)
C2—C12	1.4318 (16)	C14—H14	0.9500
C2—C3	1.5338 (15)	C15—C16	1.3601 (18)
C3—C4	1.5049 (16)	C15—H15	0.9500
C3—C17	1.5301 (15)	C16—H16	0.9500
C3—H3	1.0000	C17—C18	1.3844 (16)
C4—C5	1.3571 (16)	C17—C22	1.3889 (17)
C4—C8	1.4360 (16)	C18—C19	1.3904 (16)
C5—C6	1.5002 (16)	C18—H18	0.9500
C6—C7	1.5308 (16)	C19—C20	1.3908 (18)
C6—H6A	0.9900	C19—H19	0.9500
C6—H6B	0.9900	C20—C21	1.3872 (17)
C7—C8	1.5257 (17)	C20—C23	1.5093 (16)
C7—H7A	0.9900	C21—C22	1.3876 (16)
C7—H7B	0.9900	C21—H21	0.9500
C9—C10	1.3571 (17)	C22—H22	0.9500
C9—H9	0.9500	C23—H23A	0.9800
C10—C11	1.4158 (17)	C23—H23B	0.9800
C10—H10	0.9500	C23—H23C	0.9800
C5—N1—C1	119.46 (10)	C16—C11—C10	121.29 (11)
C5—N1—H1	115.4 (10)	C16—C11—C12	119.57 (11)
C1—N1—H1	123.1 (10)	C10—C11—C12	119.11 (11)
C2—C1—N1	121.12 (10)	C13—C12—C11	117.47 (11)
C2—C1—C9	121.35 (11)	C13—C12—C2	122.52 (11)
N1—C1—C9	117.52 (10)	C11—C12—C2	120.01 (11)
C1—C2—C12	118.24 (10)	C14—C13—C12	121.50 (11)
C1—C2—C3	121.76 (10)	C14—C13—H13	119.2
C12—C2—C3	119.95 (10)	C12—C13—H13	119.2
C4—C3—C17	111.17 (9)	C13—C14—C15	120.54 (12)
C4—C3—C2	109.12 (9)	C13—C14—H14	119.7
C17—C3—C2	111.26 (9)	C15—C14—H14	119.7
C4—C3—H3	108.4	C16—C15—C14	119.50 (12)
C17—C3—H3	108.4	C16—C15—H15	120.3
C2—C3—H3	108.4	C14—C15—H15	120.3
C5—C4—C8	108.82 (11)	C15—C16—C11	121.41 (11)
C5—C4—C3	123.27 (10)	C15—C16—H16	119.3
C8—C4—C3	127.91 (11)	C11—C16—H16	119.3
N1—C5—C4	123.07 (11)	C18—C17—C22	117.82 (11)
N1—C5—C6	122.75 (11)	C18—C17—C3	122.06 (10)
C4—C5—C6	114.18 (11)	C22—C17—C3	120.12 (10)
C5—C6—C7	102.61 (10)	C17—C18—C19	121.28 (11)
C5—C6—H6A	111.2	C17—C18—H18	119.4
C7—C6—H6A	111.2	C19—C18—H18	119.4
C5—C6—H6B	111.2	C18—C19—C20	120.83 (11)
C7—C6—H6B	111.2	C18—C19—H19	119.6
H6A—C6—H6B	109.2	C20—C19—H19	119.6
C8—C7—C6	105.69 (9)	C21—C20—C19	117.84 (11)
C8—C7—H7A	110.6	C21—C20—C23	121.01 (11)
C6—C7—H7A	110.6	C19—C20—C23	121.15 (11)
C8—C7—H7B	110.6	C20—C21—C22	121.15 (11)
C6—C7—H7B	110.6	C20—C21—H21	119.4
H7A—C7—H7B	108.7	C22—C21—H21	119.4
O1—C8—C4	127.77 (12)	C21—C22—C17	121.07 (11)
O1—C8—C7	123.64 (10)	C21—C22—H22	119.5
C4—C8—C7	108.59 (10)	C17—C22—H22	119.5
C10—C9—C1	120.71 (11)	C20—C23—H23A	109.5
C10—C9—H9	119.6	C20—C23—H23B	109.5
C1—C9—H9	119.6	H23A—C23—H23B	109.5
C9—C10—C11	120.54 (11)	C20—C23—H23C	109.5
C9—C10—H10	119.7	H23A—C23—H23C	109.5
C11—C10—H10	119.7	H23B—C23—H23C	109.5
C5—N1—C1—C2	−8.76 (16)	C9—C10—C11—C16	−178.39 (11)
C5—N1—C1—C9	170.95 (10)	C9—C10—C11—C12	−0.31 (17)
N1—C1—C2—C12	179.22 (10)	C16—C11—C12—C13	0.79 (16)
C9—C1—C2—C12	−0.47 (16)	C10—C11—C12—C13	−177.32 (10)
N1—C1—C2—C3	−3.34 (16)	C16—C11—C12—C2	179.77 (10)
C9—C1—C2—C3	176.96 (10)	C10—C11—C12—C2	1.65 (16)
C1—C2—C3—C4	13.56 (14)	C1—C2—C12—C13	177.68 (10)
C12—C2—C3—C4	−169.04 (10)	C3—C2—C12—C13	0.19 (16)
C1—C2—C3—C17	−109.46 (12)	C1—C2—C12—C11	−1.24 (16)
C12—C2—C3—C17	67.93 (13)	C3—C2—C12—C11	−178.73 (9)
C17—C3—C4—C5	109.07 (12)	C11—C12—C13—C14	0.08 (17)
C2—C3—C4—C5	−14.00 (15)	C2—C12—C13—C14	−178.86 (11)
C17—C3—C4—C8	−70.90 (14)	C12—C13—C14—C15	−0.67 (18)
C2—C3—C4—C8	166.03 (11)	C13—C14—C15—C16	0.35 (18)
C1—N1—C5—C4	8.74 (17)	C14—C15—C16—C11	0.55 (18)
C1—N1—C5—C6	−170.53 (10)	C10—C11—C16—C15	176.95 (11)
C8—C4—C5—N1	−176.27 (10)	C12—C11—C16—C15	−1.12 (17)
C3—C4—C5—N1	3.75 (17)	C4—C3—C17—C18	103.97 (13)
C8—C4—C5—C6	3.06 (14)	C2—C3—C17—C18	−134.18 (11)
C3—C4—C5—C6	−176.92 (10)	C4—C3—C17—C22	−76.38 (13)
N1—C5—C6—C7	175.76 (10)	C2—C3—C17—C22	45.46 (15)
C4—C5—C6—C7	−3.57 (13)	C22—C17—C18—C19	−0.29 (18)
C5—C6—C7—C8	2.56 (12)	C3—C17—C18—C19	179.36 (11)
C5—C4—C8—O1	178.03 (11)	C17—C18—C19—C20	−0.19 (19)
C3—C4—C8—O1	−2.0 (2)	C18—C19—C20—C21	−0.13 (19)
C5—C4—C8—C7	−1.15 (13)	C18—C19—C20—C23	179.35 (12)
C3—C4—C8—C7	178.82 (11)	C19—C20—C21—C22	0.94 (18)
C6—C7—C8—O1	179.74 (11)	C23—C20—C21—C22	−178.54 (11)
C6—C7—C8—C4	−1.04 (12)	C20—C21—C22—C17	−1.46 (19)
C2—C1—C9—C10	1.84 (17)	C18—C17—C22—C21	1.10 (18)
N1—C1—C9—C10	−177.87 (10)	C3—C17—C22—C21	−178.56 (11)
C1—C9—C10—C11	−1.41 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.902 (17)	1.983 (17)	2.8519 (13)	161.2 (14)
C15—H15···Cg1ii	0.95	3.00	3.8110 (15)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C17–C22 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.902 (17)	1.983 (17)	2.8519 (13)	161.2 (14)
C15—H15⋯Cg1ii	0.95	3.00	3.8110 (15)	145

Symmetry codes: (i) ; (ii) .