4-(4-Fluoro-phen-yl)-2-oxo-1,2,5,6-tetra-hydro-benzo[h]quinoline-3-carbonitrile.

In the mol-ecule of the title compound, C(20)H(13)FN(2)O, the fluoro-phenyl ring is oriented at a dihedral angle of 72.76 (3)° with respect to the fused benzene ring. In the crystal structure, inter-molecular N-H⋯O, C-H⋯O and C-H⋯F inter-actions link the mol-ecules 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 inter-action is also present. The O atom and two of the CH(2) 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 = 316.32

Triclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.144

S = 1.00

2656 reflections

240 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

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 ▶).

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

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

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

C20H13FN2O	Z = 2
Mr = 316.32	F(000) = 328
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0683P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2656 reflections	Δρmax = 0.15 e Å−3
240 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods

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	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)

	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)

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)

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···Cg3iv	0.93	2.90	3.671 (3)	141

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⋯Cg3iv	0.93	2.90	3.671 (3)	141

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .