8,8-Dimethyl-8,9-dihydro-7H-chromeno[2,3-b]quinoline-10,12-dione.

In the title compound, C(18)H(15)NO(3), the fused benzopyran and pyridine rings are essentially coplanar [r.m.s. deviation = 0.0533 Å with a maximum deviation of 0.080 (1) Å for a benzene C atom]. The cyclo-hexa-none ring adopts an envelope conformation with the dimethyl-substituted C atom 0.660 (2) Å out of the plane formed by the remaining ring atoms (r.m.s. deviation = 0.0305 Å). The dihedral angle between the mean planes of the pyran and cyclo-hexa-none rings is 12.95 (6)°. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, leading to chains running along [011].

Related literature

For the uses and biological importance of diketones, see: Bennett et al. (1999 ▶); Sato et al. (2008 ▶). For a related structure, see: Öztürk Yildirim et al. (2012) ▶.

Experimental

Crystal data

C18H15NO3

M = 293.31

Triclinic,

a = 7.4426 (6) Å

b = 10.5117 (9) Å

c = 10.6887 (9) Å

α = 60.939 (4)°

β = 88.107 (5)°

γ = 77.546 (5)°

V = 711.22 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.972, T max = 0.982

10655 measured reflections

2949 independent reflections

2427 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.118

S = 1.05

2949 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813001050/pv2617sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001050/pv2617Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001050/pv2617Isup3.cml

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

C18H15NO3	Z = 2
Mr = 293.31	F(000) = 308
Triclinic, P1	Dx = 1.370 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4426 (6) Å	Cell parameters from 2949 reflections
b = 10.5117 (9) Å	θ = 2.2–26.5°
c = 10.6887 (9) Å	µ = 0.09 mm−1
α = 60.939 (4)°	T = 293 K
β = 88.107 (5)°	Block, colourless
γ = 77.546 (5)°	0.30 × 0.25 × 0.20 mm
V = 711.22 (10) Å3

Bruker SMART APEXII area-detector diffractometer	2949 independent reflections
Radiation source: fine-focus sealed tube	2427 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scans	θmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
Tmin = 0.972, Tmax = 0.982	k = −13→13
10655 measured reflections	l = −13→13

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0598P)2 + 0.1006P] where P = (Fo2 + 2Fc2)/3
2949 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.01482 (17)	0.15363 (14)	0.17863 (13)	0.0415 (3)
C2	0.05259 (16)	0.17700 (13)	0.29891 (12)	0.0375 (3)
C3	0.17358 (16)	0.07117 (13)	0.41692 (12)	0.0388 (3)
H3	0.2332	−0.0190	0.4224	0.047*
C4	0.20560 (16)	0.09954 (13)	0.52620 (12)	0.0382 (3)
C5	0.33905 (17)	−0.01133 (14)	0.65130 (13)	0.0431 (3)
C6	0.37866 (19)	0.03085 (15)	0.76134 (13)	0.0485 (3)
H6A	0.5082	−0.0106	0.7958	0.058*
H6B	0.3072	−0.0154	0.8423	0.058*
C7	0.33647 (18)	0.19874 (14)	0.70916 (13)	0.0469 (3)
C8	0.13932 (19)	0.26760 (16)	0.63542 (14)	0.0518 (3)
H8A	0.0525	0.2290	0.7066	0.062*
H8B	0.1136	0.3750	0.5966	0.062*
C9	0.10985 (16)	0.23518 (13)	0.51692 (12)	0.0406 (3)
C10	−0.03248 (16)	0.30872 (13)	0.29978 (13)	0.0387 (3)
C11	−0.18038 (16)	0.41066 (14)	0.06841 (12)	0.0405 (3)
C12	−0.10695 (16)	0.28199 (14)	0.05958 (13)	0.0410 (3)
C13	−0.15013 (18)	0.28050 (16)	−0.06622 (13)	0.0488 (3)
H13	−0.1045	0.1951	−0.0738	0.059*
C14	−0.2593 (2)	0.40430 (17)	−0.17835 (14)	0.0542 (4)
H14	−0.2865	0.4028	−0.2618	0.065*
C15	−0.32914 (18)	0.53168 (16)	−0.16751 (14)	0.0523 (3)
H15	−0.4027	0.6152	−0.2441	0.063*
C16	−0.29078 (18)	0.53585 (15)	−0.04437 (14)	0.0481 (3)
H16	−0.3382	0.6213	−0.0372	0.058*
C17	0.3488 (2)	0.22292 (19)	0.83847 (16)	0.0643 (4)
H17A	0.4726	0.1818	0.8832	0.096*
H17B	0.2653	0.1741	0.9063	0.096*
H17C	0.3161	0.3280	0.8070	0.096*
C18	0.4756 (2)	0.27038 (17)	0.60480 (16)	0.0608 (4)
H18A	0.5975	0.2276	0.6532	0.091*
H18B	0.4458	0.3761	0.5704	0.091*
H18C	0.4711	0.2525	0.5251	0.091*
N1	−0.00885 (14)	0.33841 (12)	0.40449 (11)	0.0440 (3)
O1	0.08122 (15)	0.03625 (11)	0.17871 (10)	0.0603 (3)
O2	0.40972 (15)	−0.13281 (11)	0.66438 (11)	0.0630 (3)
O3	−0.14882 (12)	0.42254 (9)	0.18821 (9)	0.0467 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0459 (7)	0.0410 (7)	0.0389 (6)	−0.0114 (5)	0.0027 (5)	−0.0201 (5)
C2	0.0396 (6)	0.0378 (6)	0.0357 (6)	−0.0107 (5)	0.0034 (5)	−0.0178 (5)
C3	0.0403 (6)	0.0353 (6)	0.0399 (6)	−0.0082 (5)	0.0029 (5)	−0.0180 (5)
C4	0.0397 (6)	0.0375 (6)	0.0357 (6)	−0.0092 (5)	0.0016 (5)	−0.0164 (5)
C5	0.0449 (7)	0.0393 (7)	0.0391 (6)	−0.0088 (5)	−0.0003 (5)	−0.0149 (5)
C6	0.0535 (7)	0.0471 (7)	0.0373 (6)	−0.0078 (6)	−0.0067 (5)	−0.0157 (6)
C7	0.0558 (8)	0.0474 (7)	0.0386 (6)	−0.0082 (6)	−0.0045 (5)	−0.0229 (6)
C8	0.0595 (8)	0.0523 (8)	0.0439 (7)	0.0013 (6)	−0.0055 (6)	−0.0288 (6)
C9	0.0423 (6)	0.0415 (6)	0.0364 (6)	−0.0067 (5)	0.0011 (5)	−0.0190 (5)
C10	0.0378 (6)	0.0391 (6)	0.0365 (6)	−0.0066 (5)	0.0005 (5)	−0.0173 (5)
C11	0.0392 (6)	0.0464 (7)	0.0349 (6)	−0.0116 (5)	0.0018 (5)	−0.0186 (5)
C12	0.0429 (6)	0.0448 (7)	0.0359 (6)	−0.0150 (5)	0.0038 (5)	−0.0182 (5)
C13	0.0546 (8)	0.0542 (8)	0.0405 (7)	−0.0157 (6)	0.0023 (6)	−0.0239 (6)
C14	0.0587 (8)	0.0662 (9)	0.0370 (7)	−0.0182 (7)	−0.0020 (6)	−0.0227 (6)
C15	0.0487 (7)	0.0557 (8)	0.0383 (7)	−0.0090 (6)	−0.0044 (5)	−0.0130 (6)
C16	0.0462 (7)	0.0462 (7)	0.0431 (7)	−0.0060 (6)	−0.0022 (5)	−0.0167 (6)
C17	0.0774 (10)	0.0703 (10)	0.0496 (8)	−0.0050 (8)	−0.0112 (7)	−0.0366 (8)
C18	0.0758 (10)	0.0598 (9)	0.0538 (8)	−0.0271 (8)	0.0013 (7)	−0.0283 (7)
N1	0.0480 (6)	0.0430 (6)	0.0397 (5)	−0.0025 (5)	−0.0026 (4)	−0.0221 (5)
O1	0.0808 (7)	0.0487 (6)	0.0534 (6)	−0.0004 (5)	−0.0115 (5)	−0.0312 (5)
O2	0.0751 (7)	0.0440 (6)	0.0594 (6)	0.0067 (5)	−0.0183 (5)	−0.0241 (5)
O3	0.0520 (5)	0.0431 (5)	0.0398 (5)	0.0021 (4)	−0.0087 (4)	−0.0208 (4)

C1—O1	1.2259 (15)	C9—N1	1.3386 (15)
C1—C12	1.4635 (17)	C10—N1	1.3256 (15)
C1—C2	1.4672 (16)	C10—O3	1.3559 (14)
C2—C3	1.3854 (16)	C11—O3	1.3778 (14)
C2—C10	1.3971 (17)	C11—C16	1.3849 (17)
C3—C4	1.3775 (16)	C11—C12	1.3924 (18)
C3—H3	0.9300	C12—C13	1.4010 (17)
C4—C9	1.4070 (17)	C13—C14	1.3723 (19)
C4—C5	1.4857 (16)	C13—H13	0.9300
C5—O2	1.2118 (15)	C14—C15	1.387 (2)
C5—C6	1.5009 (17)	C14—H14	0.9300
C6—C7	1.5299 (19)	C15—C16	1.3792 (18)
C6—H6A	0.9700	C15—H15	0.9300
C6—H6B	0.9700	C16—H16	0.9300
C7—C18	1.526 (2)	C17—H17A	0.9600
C7—C17	1.5308 (17)	C17—H17B	0.9600
C7—C8	1.5369 (18)	C17—H17C	0.9600
C8—C9	1.4963 (17)	C18—H18A	0.9600
C8—H8A	0.9700	C18—H18B	0.9600
C8—H8B	0.9700	C18—H18C	0.9600
O1—C1—C12	123.35 (11)	N1—C10—O3	112.77 (10)
O1—C1—C2	122.30 (11)	N1—C10—C2	125.36 (11)
C12—C1—C2	114.34 (10)	O3—C10—C2	121.86 (10)
C3—C2—C10	116.41 (11)	O3—C11—C16	115.67 (11)
C3—C2—C1	122.35 (11)	O3—C11—C12	122.82 (11)
C10—C2—C1	121.25 (11)	C16—C11—C12	121.51 (11)
C4—C3—C2	119.96 (11)	C11—C12—C13	118.32 (12)
C4—C3—H3	120.0	C11—C12—C1	120.13 (11)
C2—C3—H3	120.0	C13—C12—C1	121.55 (12)
C3—C4—C9	118.78 (10)	C14—C13—C12	120.39 (13)
C3—C4—C5	120.42 (11)	C14—C13—H13	119.8
C9—C4—C5	120.79 (10)	C12—C13—H13	119.8
O2—C5—C4	120.40 (11)	C13—C14—C15	120.18 (12)
O2—C5—C6	121.68 (11)	C13—C14—H14	119.9
C4—C5—C6	117.90 (11)	C15—C14—H14	119.9
C5—C6—C7	115.45 (10)	C16—C15—C14	120.73 (12)
C5—C6—H6A	108.4	C16—C15—H15	119.6
C7—C6—H6A	108.4	C14—C15—H15	119.6
C5—C6—H6B	108.4	C15—C16—C11	118.85 (13)
C7—C6—H6B	108.4	C15—C16—H16	120.6
H6A—C6—H6B	107.5	C11—C16—H16	120.6
C18—C7—C6	110.08 (12)	C7—C17—H17A	109.5
C18—C7—C17	109.31 (11)	C7—C17—H17B	109.5
C6—C7—C17	109.11 (11)	H17A—C17—H17B	109.5
C18—C7—C8	110.61 (11)	C7—C17—H17C	109.5
C6—C7—C8	108.18 (11)	H17A—C17—H17C	109.5
C17—C7—C8	109.53 (11)	H17B—C17—H17C	109.5
C9—C8—C7	113.02 (11)	C7—C18—H18A	109.5
C9—C8—H8A	109.0	C7—C18—H18B	109.5
C7—C8—H8A	109.0	H18A—C18—H18B	109.5
C9—C8—H8B	109.0	C7—C18—H18C	109.5
C7—C8—H8B	109.0	H18A—C18—H18C	109.5
H8A—C8—H8B	107.8	H18B—C18—H18C	109.5
N1—C9—C4	122.22 (11)	C10—N1—C9	117.23 (10)
N1—C9—C8	117.88 (11)	C10—O3—C11	119.42 (10)
C4—C9—C8	119.90 (11)
O1—C1—C2—C3	3.61 (19)	C1—C2—C10—N1	178.92 (10)
C12—C1—C2—C3	−176.04 (10)	C3—C2—C10—O3	177.77 (10)
O1—C1—C2—C10	−176.52 (12)	C1—C2—C10—O3	−2.11 (18)
C12—C1—C2—C10	3.83 (16)	O3—C11—C12—C13	178.89 (10)
C10—C2—C3—C4	−0.61 (16)	C16—C11—C12—C13	−1.16 (18)
C1—C2—C3—C4	179.27 (10)	O3—C11—C12—C1	−2.24 (18)
C2—C3—C4—C9	1.67 (17)	C16—C11—C12—C1	177.71 (11)
C2—C3—C4—C5	−178.27 (10)	O1—C1—C12—C11	178.63 (12)
C3—C4—C5—O2	−6.06 (18)	C2—C1—C12—C11	−1.73 (16)
C9—C4—C5—O2	174.00 (12)	O1—C1—C12—C13	−2.54 (19)
C3—C4—C5—C6	175.48 (10)	C2—C1—C12—C13	177.10 (10)
C9—C4—C5—C6	−4.47 (17)	C11—C12—C13—C14	1.21 (19)
O2—C5—C6—C7	159.80 (13)	C1—C12—C13—C14	−177.64 (11)
C4—C5—C6—C7	−21.76 (17)	C12—C13—C14—C15	−0.5 (2)
C5—C6—C7—C18	−70.62 (14)	C13—C14—C15—C16	−0.2 (2)
C5—C6—C7—C17	169.43 (11)	C14—C15—C16—C11	0.3 (2)
C5—C6—C7—C8	50.34 (15)	O3—C11—C16—C15	−179.63 (10)
C18—C7—C8—C9	65.43 (15)	C12—C11—C16—C15	0.42 (19)
C6—C7—C8—C9	−55.20 (15)	O3—C10—N1—C9	−177.28 (10)
C17—C7—C8—C9	−174.03 (12)	C2—C10—N1—C9	1.78 (18)
C3—C4—C9—N1	−1.11 (18)	C4—C9—N1—C10	−0.57 (18)
C5—C4—C9—N1	178.84 (10)	C8—C9—N1—C10	179.47 (11)
C3—C4—C9—C8	178.85 (11)	N1—C10—O3—C11	177.09 (9)
C5—C4—C9—C8	−1.21 (17)	C2—C10—O3—C11	−2.00 (17)
C7—C8—C9—N1	−147.69 (12)	C16—C11—O3—C10	−175.71 (10)
C7—C8—C9—C4	32.35 (17)	C12—C11—O3—C10	4.23 (17)
C3—C2—C10—N1	−1.20 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O2i	0.93	2.43	3.250 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O2i	0.93	2.43	3.250 (2)	147

Symmetry code: (i) .