4-(4-Fluoro­phen­yl)-2-oxo-1,2,5,6-tetra­hydro­benzo[h]quinoline-3-carbonitrile

Zhang, J.; Ding, J.; Yan, S.; Rong, L.; Xu, L.

doi:10.1107/S1600536809017991

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1354

doi:10.1107/S1600536809017991

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4-(4-Fluorophenyl)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile

Jinpeng Zhang,^a Jie Ding,^b Shu Yan,^b Liangce Rong ^b and Lichun Xu ^a ^*

^aDepartment of Public Health, Xuzhou Medical College, Xuzhou 221000, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
^*Correspondence e-mail: yanshu126@126.com

(Received 8 May 2009; accepted 13 May 2009; online 20 May 2009)

In the molecule of the title compound, C₂₀H₁₃FN₂O, the fluorophenyl ring is oriented at a dihedral angle of 72.76 (3)° with respect to the fused benzene ring. In the crystal structure, intermolecular N—H⋯O, C—H⋯O and C—H⋯F interactions link the molecules into chains. π–π contacts between the quinoline and benzene rings [centroid–centroid distance = 3.918 (3) Å] may further stabilize the structure. A weak C—H⋯π interaction is also present. The O atom and two of the CH₂ groups of the quinoline ring system are disordered over two positions. The O atom was refined with occupancies of 0.489 (17) and 0.511 (17), while C and H atoms were refined with occupancies of 0.435 (13) and 0.565 (13).

Related literature

For general background to substituted six-membered lactams, see: Daly (1998 ); Plunkett (1994 ); Robertson et al. (1986 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₀H₁₃FN₂O
M_r = 316.32
Triclinic, $[P \overline 1]$
a = 8.116 (10) Å
b = 9.278 (12) Å
c = 11.263 (14) Å
α = 98.674 (19)°
β = 105.095 (17)°
γ = 104.846 (18)°
V = 769.7 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.48 × 0.35 × 0.33 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.956, T_max = 0.970
3950 measured reflections
2656 independent reflections
1399 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.144
S = 1.00
2656 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.08	2.883 (3)	155
C7—H7⋯O1ⁱ	0.93	2.35	3.223 (3)	157
C12—H12B⋯O1ⁱⁱ	0.97	2.21	2.863 (3)	124
C13—H13B⋯F1ⁱⁱⁱ	0.97	2.42	3.270 (3)	147
C15—H15⋯Cg3^iv	0.93	2.90	3.671 (3)	141
Symmetry codes: (i) -x, -y, -z+1; (ii) x+1, y, z; (iii) -x+1, -y+1, -z; (iv) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017991/hk2684sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017991/hk2684Isup2.hkl

checkCIF report

Comment top

Substituted six-membered lactams have attracted the attention of synthetic organic chemists for many years because these structural features are found in a wide variety of naturally occurring alkaloids (Daly, 1998; Plunkett, 1994). Since compounds with these scaffolds have been shown to exhibit significant pharmacological properties, medicinal chemists often incorporate these motifs in the design of novel biologically active molecules. For example, compounds Arnrinone 1 and Milrinone 2 are the cardiotonic drugs (Robertson et al., 1986) and that have been found to display effective activities on therapy of miocardial infarction. Development of a general and efficient synthetic strategy to synthesize those compounds is still desired. We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (N1/C1-C5), C (C6-C11) and D (C14-C19) are, of course, planar and they are oriented at dihedral angles of A/C = 3.57 (3), A/D = 76.11 (3) and C/D = 72.76 (3) °. Ring B (C4-C6/C11-C13) is not planar, and adopts twisted conformation.

In the crystal structure, intermolecular N-H···O, C-H···O and C-H···F interactions (Table 1) link the molecules into chains (Fig. 2), in which they may be effective in the stabilization of the structure. The π···π contact between the quinoline and the benzene rings, Cg1—Cg3ⁱ [symmetry code: (i) 1 - x, -y, 1 - z, where Cg1 and Cg3 are centroids of the rings A (N1/C1-C5) and C (C6-C11), respectively] may further stabilize the structure, with centroid-centroid distance of 3.918 (3) Å. There also exists a weak C-H···π interaction (Table 1).

Related literature top

For general background to substituted six-membered lactams, see: Daly (1998); Plunkett (1994); Robertson et al. (1986). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the reaction of 3,4-dihydronaphthalen-1(2H) -one (2 mmol), aromatic aldehydes (2 mmol), malononitrile (3 mmol) and NaOH (2 mmol) under solvent-free conditions using heating method.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

4-(4-Fluorophenyl)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3- carbonitrile top

Crystal data top

C₂₀H₁₃FN₂O	Z = 2
M_r = 316.32	F(000) = 328
Triclinic, P1	D_x = 1.365 Mg m⁻³
Hall symbol: -P 1	Melting point > 598 K
a = 8.116 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.278 (12) Å	Cell parameters from 929 reflections
c = 11.263 (14) Å	θ = 2.3–25.4°
α = 98.674 (19)°	µ = 0.09 mm⁻¹
β = 105.095 (17)°	T = 298 K
γ = 104.846 (18)°	Block, colourless
V = 769.7 (16) Å³	0.48 × 0.35 × 0.33 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2656 independent reflections
Radiation source: fine-focus sealed tube	1399 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.956, T_max = 0.970	k = −11→8
3950 measured reflections	l = −9→13

Refinement top

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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.144	w = 1/[σ²(F_o²) + (0.0683P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2656 reflections	Δρ_max = 0.15 e Å⁻³
240 parameters	Δρ_min = −0.17 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₀H₁₃FN₂O	γ = 104.846 (18)°
M_r = 316.32	V = 769.7 (16) Å³
Triclinic, P1	Z = 2
a = 8.116 (10) Å	Mo Kα radiation
b = 9.278 (12) Å	µ = 0.09 mm⁻¹
c = 11.263 (14) Å	T = 298 K
α = 98.674 (19)°	0.48 × 0.35 × 0.33 mm
β = 105.095 (17)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2656 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1399 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.970	R_int = 0.020
3950 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	240 parameters
wR(F²) = 0.144	H-atom parameters constrained
S = 1.00	Δρ_max = 0.15 e Å⁻³
2656 reflections	Δρ_min = −0.17 e Å⁻³

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	Occ. (<1)
F1	0.2899 (2)	0.4261 (2)	−0.18711 (16)	0.1127 (7)
N1	0.2029 (3)	0.1315 (2)	0.45914 (18)	0.0580 (6)
H1	0.1926	0.0948	0.5235	0.070*
N2	−0.2136 (3)	0.1660 (3)	0.0916 (2)	0.0781 (7)
O1	−0.101 (3)	0.0761 (19)	0.3875 (16)	0.063 (2)	0.489 (17)
O1'	−0.100 (2)	0.0203 (19)	0.3604 (16)	0.063 (2)	0.511 (17)
C1	0.0482 (3)	0.1170 (3)	0.3667 (2)	0.0589 (7)
C2	0.0742 (3)	0.1847 (3)	0.2646 (2)	0.0474 (6)
C3	0.2423 (3)	0.2493 (3)	0.2576 (2)	0.0449 (6)
C4	0.3947 (3)	0.2594 (3)	0.3564 (2)	0.0514 (7)
C5	0.3716 (3)	0.1991 (3)	0.4576 (2)	0.0441 (6)
C6	0.5250 (3)	0.2014 (3)	0.5626 (2)	0.0472 (6)
C7	0.5053 (4)	0.1393 (3)	0.6645 (2)	0.0611 (7)
H7	0.3908	0.0975	0.6694	0.073*
C8	0.6514 (4)	0.1387 (3)	0.7579 (2)	0.0673 (8)
H8	0.6354	0.0973	0.8259	0.081*
C9	0.8191 (4)	0.1978 (3)	0.7521 (3)	0.0705 (8)
H9	0.9181	0.1954	0.8149	0.085*
C10	0.8420 (4)	0.2613 (4)	0.6529 (3)	0.0817 (9)
H10	0.9575	0.3021	0.6496	0.098*
C11	0.6977 (4)	0.2660 (3)	0.5580 (2)	0.0652 (8)
C12	0.7151 (13)	0.2943 (16)	0.4310 (10)	0.060 (2)	0.435 (13)
H12A	0.8345	0.3611	0.4429	0.072*	0.435 (13)
H12B	0.6964	0.1979	0.3740	0.072*	0.435 (13)
C13	0.5770 (13)	0.3675 (14)	0.3755 (13)	0.061 (3)	0.435 (13)
H13A	0.5955	0.4640	0.4323	0.073*	0.435 (13)
H13B	0.5872	0.3880	0.2953	0.073*	0.435 (13)
C12'	0.7237 (10)	0.3759 (13)	0.4687 (7)	0.069 (2)	0.565 (13)
H12C	0.7097	0.4729	0.5027	0.083*	0.565 (13)
H12D	0.8432	0.3954	0.4608	0.083*	0.565 (13)
C13'	0.5852 (10)	0.3014 (12)	0.3417 (7)	0.059 (2)	0.565 (13)
H13C	0.6068	0.2095	0.3046	0.071*	0.565 (13)
H13D	0.5936	0.3710	0.2858	0.071*	0.565 (13)
C14	0.2601 (3)	0.3026 (3)	0.1417 (2)	0.0493 (6)
C15	0.2276 (4)	0.4341 (3)	0.1176 (3)	0.0681 (8)
H15	0.1976	0.4956	0.1764	0.082*
C16	0.2388 (4)	0.4774 (4)	0.0065 (3)	0.0769 (9)
H16	0.2165	0.5671	−0.0098	0.092*
C17	0.2827 (4)	0.3865 (4)	−0.0771 (3)	0.0729 (9)
C18	0.3162 (4)	0.2565 (4)	−0.0566 (3)	0.0858 (10)
H18	0.3456	0.1957	−0.1163	0.103*
C19	0.3064 (4)	0.2146 (4)	0.0539 (3)	0.0769 (9)
H19	0.3314	0.1256	0.0696	0.092*
C20	−0.0853 (4)	0.1739 (3)	0.1674 (2)	0.0561 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0932 (13)	0.1675 (19)	0.0723 (12)	0.0028 (12)	0.0250 (10)	0.0801 (12)
N1	0.0489 (13)	0.0912 (17)	0.0447 (12)	0.0206 (12)	0.0199 (11)	0.0405 (12)
N2	0.0698 (17)	0.100 (2)	0.0663 (16)	0.0261 (15)	0.0106 (14)	0.0435 (15)
O1	0.0480 (12)	0.100 (8)	0.058 (6)	0.025 (5)	0.027 (3)	0.044 (5)
O1'	0.0480 (12)	0.100 (8)	0.058 (6)	0.025 (5)	0.027 (3)	0.044 (5)
C1	0.0495 (16)	0.088 (2)	0.0505 (16)	0.0231 (15)	0.0207 (14)	0.0367 (15)
C2	0.0511 (15)	0.0574 (16)	0.0420 (14)	0.0187 (13)	0.0187 (12)	0.0256 (12)
C3	0.0535 (15)	0.0467 (15)	0.0418 (14)	0.0153 (12)	0.0212 (12)	0.0207 (12)
C4	0.0509 (15)	0.0569 (16)	0.0503 (15)	0.0113 (13)	0.0198 (13)	0.0266 (13)
C5	0.0461 (14)	0.0482 (15)	0.0414 (14)	0.0141 (12)	0.0164 (12)	0.0163 (12)
C6	0.0485 (15)	0.0505 (16)	0.0426 (14)	0.0140 (13)	0.0143 (12)	0.0131 (12)
C7	0.0549 (17)	0.078 (2)	0.0479 (16)	0.0119 (14)	0.0124 (13)	0.0282 (14)
C8	0.072 (2)	0.068 (2)	0.0521 (17)	0.0144 (16)	0.0056 (16)	0.0245 (15)
C9	0.064 (2)	0.080 (2)	0.0585 (19)	0.0225 (17)	0.0024 (15)	0.0179 (16)
C10	0.0517 (18)	0.114 (3)	0.080 (2)	0.0235 (18)	0.0158 (16)	0.037 (2)
C11	0.0536 (17)	0.085 (2)	0.0588 (17)	0.0193 (15)	0.0158 (14)	0.0276 (16)
C12	0.043 (4)	0.072 (6)	0.068 (5)	0.015 (5)	0.020 (4)	0.026 (4)
C13	0.065 (5)	0.062 (6)	0.057 (5)	0.012 (4)	0.024 (4)	0.024 (4)
C12'	0.055 (3)	0.079 (5)	0.071 (4)	0.010 (4)	0.021 (3)	0.029 (4)
C13'	0.049 (3)	0.071 (5)	0.062 (5)	0.010 (4)	0.024 (3)	0.032 (4)
C14	0.0499 (15)	0.0571 (16)	0.0440 (15)	0.0110 (13)	0.0178 (12)	0.0253 (13)
C15	0.084 (2)	0.0655 (19)	0.0653 (19)	0.0249 (16)	0.0280 (16)	0.0360 (15)
C16	0.077 (2)	0.075 (2)	0.079 (2)	0.0134 (17)	0.0159 (18)	0.0533 (18)
C17	0.0537 (18)	0.108 (3)	0.0502 (18)	−0.0009 (18)	0.0128 (14)	0.0486 (19)
C18	0.104 (3)	0.112 (3)	0.064 (2)	0.038 (2)	0.0474 (19)	0.041 (2)
C19	0.112 (3)	0.086 (2)	0.0628 (19)	0.046 (2)	0.0480 (19)	0.0436 (17)
C20	0.0602 (18)	0.0676 (18)	0.0495 (17)	0.0195 (15)	0.0222 (15)	0.0318 (14)

Geometric parameters (Å, º) top

F1—C17	1.356 (3)	C10—C11	1.381 (4)
N1—C5	1.358 (3)	C10—H10	0.9300
N1—C1	1.367 (3)	C11—C12	1.528 (9)
N1—H1	0.8600	C11—C12'	1.550 (8)
N2—C20	1.139 (3)	C12—C13	1.505 (14)
O1—C1	1.267 (18)	C12—H12A	0.9700
O1'—C1	1.279 (18)	C12—H12B	0.9700
C1—C2	1.428 (3)	C13—H13A	0.9700
C2—C3	1.370 (3)	C13—H13B	0.9700
C2—C20	1.431 (4)	C12'—C13'	1.501 (12)
C3—C4	1.404 (3)	C12'—H12C	0.9700
C3—C14	1.491 (3)	C12'—H12D	0.9700
C4—C5	1.377 (3)	C13'—H13C	0.9700
C4—C13	1.499 (10)	C13'—H13D	0.9700
C4—C13'	1.553 (8)	C14—C15	1.363 (4)
C5—C6	1.470 (3)	C14—C19	1.376 (4)
C6—C7	1.387 (3)	C15—C16	1.389 (4)
C6—C11	1.394 (4)	C15—H15	0.9300
C7—C8	1.367 (4)	C16—C17	1.347 (4)
C7—H7	0.9300	C16—H16	0.9300
C8—C9	1.354 (4)	C17—C18	1.342 (4)
C8—H8	0.9300	C18—C19	1.375 (4)
C9—C10	1.371 (4)	C18—H18	0.9300
C9—H9	0.9300	C19—H19	0.9300

C5—N1—C1	125.3 (2)	C13—C12—H12A	109.9
C5—N1—H1	117.4	C11—C12—H12A	109.9
C1—N1—H1	117.4	C13—C12—H12B	109.9
O1—C1—N1	119.7 (9)	C11—C12—H12B	109.9
O1'—C1—N1	120.2 (8)	H12A—C12—H12B	108.3
O1—C1—C2	124.0 (9)	C4—C13—C12	108.2 (9)
O1'—C1—C2	123.2 (8)	C4—C13—H13A	110.1
N1—C1—C2	114.7 (2)	C12—C13—H13A	110.1
C3—C2—C1	121.7 (2)	C4—C13—H13B	110.1
C3—C2—C20	122.2 (2)	C12—C13—H13B	110.1
C1—C2—C20	116.0 (2)	H13A—C13—H13B	108.4
C2—C3—C4	120.1 (2)	C13'—C12'—C11	108.2 (7)
C2—C3—C14	119.1 (2)	C13'—C12'—H12C	110.1
C4—C3—C14	120.8 (2)	C11—C12'—H12C	110.1
C5—C4—C3	118.8 (2)	C13'—C12'—H12D	110.1
C5—C4—C13	116.3 (5)	C11—C12'—H12D	110.1
C3—C4—C13	122.8 (5)	H12C—C12'—H12D	108.4
C5—C4—C13'	118.0 (4)	C12'—C13'—C4	109.8 (7)
C3—C4—C13'	121.8 (4)	C12'—C13'—H13C	109.7
N1—C5—C4	119.4 (2)	C4—C13'—H13C	109.7
N1—C5—C6	118.8 (2)	C12'—C13'—H13D	109.7
C4—C5—C6	121.8 (2)	C4—C13'—H13D	109.7
C7—C6—C11	118.7 (2)	H13C—C13'—H13D	108.2
C7—C6—C5	122.9 (2)	C15—C14—C19	118.4 (2)
C11—C6—C5	118.4 (2)	C15—C14—C3	122.3 (2)
C8—C7—C6	121.1 (3)	C19—C14—C3	119.2 (2)
C8—C7—H7	119.5	C14—C15—C16	120.9 (3)
C6—C7—H7	119.5	C14—C15—H15	119.5
C9—C8—C7	120.4 (3)	C16—C15—H15	119.5
C9—C8—H8	119.8	C17—C16—C15	118.4 (3)
C7—C8—H8	119.8	C17—C16—H16	120.8
C8—C9—C10	119.5 (3)	C15—C16—H16	120.8
C8—C9—H9	120.2	C18—C17—C16	122.5 (3)
C10—C9—H9	120.2	C18—C17—F1	118.7 (3)
C9—C10—C11	121.6 (3)	C16—C17—F1	118.8 (3)
C9—C10—H10	119.2	C17—C18—C19	118.9 (3)
C11—C10—H10	119.2	C17—C18—H18	120.5
C10—C11—C6	118.7 (3)	C19—C18—H18	120.5
C10—C11—C12	121.7 (4)	C18—C19—C14	120.9 (3)
C6—C11—C12	117.1 (4)	C18—C19—H19	119.6
C10—C11—C12'	120.9 (4)	C14—C19—H19	119.6
C6—C11—C12'	118.5 (4)	N2—C20—C2	178.8 (3)
C13—C12—C11	108.8 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.08	2.883 (3)	155
C7—H7···O1ⁱ	0.93	2.35	3.223 (3)	157
C12—H12B···O1ⁱⁱ	0.97	2.21	2.863 (3)	124
C13—H13B···F1ⁱⁱⁱ	0.97	2.42	3.270 (3)	147
C15—H15···Cg3^iv	0.93	2.90	3.671 (3)	141

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₃FN₂O
M_r	316.32
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.116 (10), 9.278 (12), 11.263 (14)
α, β, γ (°)	98.674 (19), 105.095 (17), 104.846 (18)
V (Å³)	769.7 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.48 × 0.35 × 0.33

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.956, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	3950, 2656, 1399
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.144, 1.00
No. of reflections	2656
No. of parameters	240
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.08	2.883 (3)	155
C7—H7···O1ⁱ	0.93	2.35	3.223 (3)	157
C12—H12B···O1ⁱⁱ	0.97	2.21	2.863 (3)	124
C13—H13B···F1ⁱⁱⁱ	0.97	2.42	3.270 (3)	147
C15—H15···Cg3^iv	0.93	2.90	3.671 (3)	141

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

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant No. 30872143) and the Foundation of Xuzhou Medical College (grant No. 08 K J50) for financial support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Daly, J. W. (1998). J. Nat. Prod. 61, 162–172. Web of Science CrossRef CAS PubMed Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Plunkett, A. O. (1994). Nat. Prod. Rep. 11, 581–590. CrossRef PubMed CAS Web of Science Google Scholar
Robertson, D. W., Beedle, E. E., Swartzendruber, J. K., Jones, N. D., Elzey, T. K., Kauffman, R. F., Wilson, H. & Hayes, J. S. (1986). J. Med. Chem. 29, 635–640. CSD CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 6| June 2009| Page o1354

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

4-(4-Fluoro­phen­yl)-2-oxo-1,2,5,6-tetra­hydro­benzo[h]quinoline-3-carbo­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-(4-Fluorophenyl)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile