11-(4-Methyl­phen­yl)-8,9-dihydro-7H-benzo[f]cyclo­penta­[b]quinolin-10(11H)-one

Yang, C.

doi:10.1107/S1600536812035659

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2746

doi:10.1107/S1600536812035659

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11-(4-Methylphenyl)-8,9-dihydro-7H-benzo[f]cyclopenta[b]quinolin-10(11H)-one

Cao Yang ^a ^*

^aThe First Affiliated Hospital of Nanjing Medical University, Nanjing 210029, People's Republic of China
^*Correspondence e-mail: ycs.bluespirit@gmail.com

(Received 30 July 2012; accepted 13 August 2012; online 23 August 2012)

In the title compound, C₂₃H₁₉NO, the naphthalene ring system and the cyclopent-2-enone ring exhibit planar conformations with maximum deviations of 0.034 (1) and 0.02 (1) Å, respectively. The 1,4-dihydropyridine ring adopts an envelope conformation with the C atom bearing the p-tolyl ring as the flap atom. Intermolecular N—H⋯O hydrogen bonds and C—H⋯π interactions 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_r = 325.39
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.124
S = 1.07
3899 reflections
231 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+2, -z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812035659/hg5239sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812035659/hg5239Isup3.cml

checkCIF report

Comment top

Many efforts have been devoted to the synthesis of quinoline and fused quinoline derivaties due to their broad spectrum of bioactivities including anti-norovirus activity (Pokhrel et al. 2012), antikinetoplastid activity (Audisio et al. 2012), antimalarial activity (Kurasawa et al. 2012). These work inspired us to assemble various types of fused quinoline skeletons and evaluate their bioactivities to study the relationship between structure and activity (SAR). Determination of the accurate structure is crucial to do SAR research. During our work on the efficient synthesis and biological study of benzo[f]cyclopenta[b]quinolins, the title compound (I) was isolated and its structure was determined by X-ray diffraction. Herein we report its crystal structure.

In the molecular structure (Fig. 1), the quinoline ring and cyclopent-2-enone ring adopts planar conformations. The atoms with maximal deviation from the the two ring are C9 and ing systr C5 with the distance of 0.034 (1)Å and 0.02 (1) Å, respectively. The dihydropyridine ring is in an envelope (or half boat) conformation, since C1/C2/N1/C4/C5 is coplanar with the largest deviation of 0.040 (1)Å(N1). However, the distance of C3 and the plane consisting of the rest five atoms is 0.212 (1)Å. Cremer & Pople puckering parameters analysis also confirms that the dihydropyridine ring adopts a envelope conformation (Cremer & Pople, 1975). Its puckering amplitude (Q), θ and ϕ are 0.156 (1)Å, 102.7 (4)° and 0.7 (5)°, respectively. The linkage between p-tolyl and dihydropyridine ring can be described by the torsion angle of C2—C3—C17—C22 (45.46 (15)°) and C4—C3—C17—C22(-76.38 (13)°) respectively. The crystal packing is stabilized by intermolecular N—H···O hydrogen bond and C—H··· π interactions (Fig. 2, Table 1).

Related literature top

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 top

In a dry 50 mL flask, cyclopentane-1,3-dione (0.10 g, 1 mmol), 4-methylbenzaldehyde (0.12 g, 1 mmol), naphthalen-2-amine (0.14 g,1 mmol), p-toluenesulfonic acid (0.2 g, 1 mmol) and water (10 mL) were mixed and then stirred at 373 K for 5 h. After completion of the reaction, as indicated by TLC, the solid product was collected by filtration and were purified by flash column chromatography (silica gel, mixtures of ethyl acetate / petroleum ether, 1:3, v/v) to afford the desired pure product. m. p.: 562-564 K; IR (KBr,ν, cm^-1): 3165, 3080, 3013, 2962, 1666, 1632, 1584, 1522, 1468, 1397, 1269, 1239, 1220, 1012, 841, 806, 748, 688, 531; ¹H NMR (400 MHz, DMSO-d₆) (δ, ppm): 10.27 (s, 1H, NH), 7.80 (q, J = 8.4 Hz, 3H, ArH), 7.37-7.28 (m, 3H, ArH), 7.05 (d, J = 8.0 Hz, 2H, ArH), 6.94 (d, J = 8.0 Hz, 2H, ArH), 5.58 (s, 1H, CH), 2.71-2.63 (m, 2H, CH₂), 2.34-2.20 (m, 2H, CH₂), 2.14 (s, 3H, CH₃); HRMS (ESI) m/z: Calcd. for C₂₃H₁₉NONa [M+Na]⁺ 348.1364, found: 348.1345.The single-crystal suitable for X-ray diffraction was obtained through slow evaporation of the ethanol solution of the title compound.

Computing details top

Data collection: CrystalClearSM Expert (Rigaku/MSC, 2009); cell refinement: CrystalClearSM Expert (Rigaku/MSC, 2009); data reduction: CrystalClearSM Expert (Rigaku/MSC, 2009); 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 (Sheldrick, 2008).

Figures top

Figure 1 The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Figure 2 The packing diagram of (I), Hydrogen bond represented by the dashed line, Cg is the centroid of the ring of C17/C18/C19/C20/C21/C22, Hydrogen atoms not involved in Hydrogen bond were omitted for clarity.

11-(4-Methylphenyl)-8,9-dihydro-7H- benzo[f]cyclopenta[b]quinolin-10(11H)-one top

Crystal data top

C₂₃H₁₉NO	F(000) = 688
M_r = 325.39	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0777P)² + 0.041P] where P = (F_o² + 2F_c²)/3
3899 reflections	(Δ/σ)_max < 0.001
231 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₃H₁₉NO	V = 1635.5 (3) Å³
M_r = 325.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.727 (1) Å	µ = 0.08 mm⁻¹
b = 11.6820 (14) Å	T = 113 K
c = 16.240 (2) Å	0.24 × 0.20 × 0.18 mm
β = 98.938 (5)°

Data collection top

Rigaku Saturn724 CCD diffractometer	3899 independent reflections
Absorption correction: multi-scan (CrystalClearSM Expert; Rigaku/MSC, 2009)	2991 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.986	R_int = 0.031
15928 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.36 e Å⁻³
3899 reflections	Δρ_min = −0.32 e Å⁻³
231 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+1/2, −z+1/2; (ii) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₉NO
M_r	325.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	8.727 (1), 11.6820 (14), 16.240 (2)
β (°)	98.938 (5)
V (Å³)	1635.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClearSM Expert; Rigaku/MSC, 2009)
T_min, T_max	0.981, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	15928, 3899, 2991
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.124, 1.07
No. of reflections	3899
No. of parameters	231
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.32

Computer programs: CrystalClearSM Expert (Rigaku/MSC, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)	145.0

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, −y+2, −z.

Acknowledgements

The author is thankful to Professor Youquan Zhu of Nankai University, China, for his kindly help with the collection of the X-ray data set, structure solution and refinement.

References

Audisio, D., Messaoudi, S., Cojean, S., Peyrat, J.-F., Brion, J.-D., Bories, C., Huteau, F., Loiseau, P. M. & Alami, M. (2012). Eur. J. Med. Chem. 52, 44–50. Web of Science CrossRef CAS PubMed Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Kurasawa, Y., Yoshida, K., Yamazaki, N., Kaji, E., Sasaki, K., Zamami, Y., Sakai, Y., Fujii, T. & Ito, H. (2012). J. Heterocycl. Chem. 49, 288–292. Web of Science CrossRef CAS Google Scholar
Pokhrel, L., Kim, Y., Nguyen, T. D. T., Prior, A. M., Lu, J., Chang, K.-O. & Hua, D. H. (2012). Bioorg. Med. Chem. Lett. 22, 3480–3484. Web of Science CrossRef CAS PubMed Google Scholar
Rigaku/MSC (2009). CrystalClearSM Expert. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 9| September 2012| Page o2746

doi:10.1107/S1600536812035659

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

11-(4-Methyl­phen­yl)-8,9-di­hydro-7H-benzo[f]cyclo­penta­[b]quinolin-10(11H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

11-(4-Methylphenyl)-8,9-dihydro-7H-benzo[f]cyclopenta[b]quinolin-10(11H)-one