Ethyl 4-methyl-1,3-dioxo-1,2,3,4-tetra-hydro-isoquinoline-4-carboxyl-ate.

In the title compound, C(13)H(13)NO(4), the fused-ring system is nearly planar, with an r.m.s. deviation of 0.0408 Å. In the crystal, mol-ecules are linked into centrosymmetric dimers by a pair of N-H⋯O hydrogen bonds. The ethyl group is disordered over two positions in a ratio of 0.758 (6):0.242 (6).

Related literature

For pharmaceutical usage of derivatives of isoquinoline-1,3(2H,4H)-dione, see: Lu et al. (2010 ▶); Tsou et al. (2008 ▶, 2009 ▶); Billamboz et al. (2011 ▶).

Experimental

Crystal data

C13H13NO4

M = 247.24

Triclinic,

a = 6.4585 (9) Å

b = 8.1999 (7) Å

c = 12.5763 (11) Å

α = 78.876 (7)°

β = 77.228 (9)°

γ = 72.354 (9)°

V = 613.28 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.38 × 0.23 × 0.09 mm

Data collection

Agilent Xcalibur Atlas Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.963, T max = 0.991

3820 measured reflections

2243 independent reflections

1659 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.135

S = 1.06

2243 reflections

170 parameters

5 restraints

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812008136/xu5472sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008136/xu5472Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008136/xu5472Isup3.cml

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

C13H13NO4	Z = 2
Mr = 247.24	F(000) = 260
Triclinic, P1	Dx = 1.339 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4585 (9) Å	Cell parameters from 1387 reflections
b = 8.1999 (7) Å	θ = 3.3–29.2°
c = 12.5763 (11) Å	µ = 0.10 mm−1
α = 78.876 (7)°	T = 293 K
β = 77.228 (9)°	Platelet, colorless
γ = 72.354 (9)°	0.38 × 0.23 × 0.09 mm
V = 613.28 (11) Å3

Agilent Xcalibur Atlas Gemini ultra diffractometer	2243 independent reflections
Radiation source: fine-focus sealed tube	1659 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 10.3592 pixels mm-1	θmax = 25.4°, θmin = 3.3°
ω scans	h = −7→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −9→9
Tmin = 0.963, Tmax = 0.991	l = −14→15
3820 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.061P)2 + 0.1013P] where P = (Fo2 + 2Fc2)/3
2243 reflections	(Δ/σ)max < 0.001
170 parameters	Δρmax = 0.18 e Å−3
5 restraints	Δρmin = −0.25 e Å−3

Experimental. 1H NMR (400 MHz, CDCl3): 8.37 (br s, 1H), 8.26 (d, J = 8.0 Hz, 1H), 7.68 (t, J = 8.0 Hz, 1H), 7.52 (t, J = 8.0 Hz, 1H), 7.41 (d, J = 7.6 Hz, 1H), 4.23-4.05 (m, 2H), 1.89 (s, 3H), 1.12 (t, J = 7.2 Hz, 3H) ppm; 13C NMR (100 MHz, CDCl3): 171.1, 169.1, 163.6, 140.1, 134.8, 128.9, 128.6, 125.9, 123.5, 62.6, 55.0, 25.1, 13.7 ppm.

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	Occ. (<1)
O1	0.2337 (3)	−0.13049 (17)	0.54786 (12)	0.0529 (4)
O2	−0.1215 (2)	0.40108 (18)	0.63638 (13)	0.0527 (4)
O3	0.1682 (3)	0.4585 (2)	0.83716 (14)	0.0734 (6)
O4	−0.0080 (3)	0.2543 (2)	0.86413 (12)	0.0610 (5)
N1	0.0689 (3)	0.13902 (19)	0.58943 (13)	0.0379 (4)
H1	−0.0268	0.1471	0.5494	0.046*
C1	0.5645 (4)	−0.1829 (3)	0.67306 (17)	0.0453 (5)
H1A	0.5636	−0.2759	0.6411	0.054*
C2	0.7280 (4)	−0.1987 (3)	0.7311 (2)	0.0559 (6)
H2	0.8373	−0.3023	0.7390	0.067*
C3	0.7288 (4)	−0.0596 (3)	0.7776 (2)	0.0578 (6)
H3	0.8405	−0.0696	0.8161	0.069*
C4	0.5663 (4)	0.0937 (3)	0.76769 (18)	0.0477 (6)
H4	0.5684	0.1858	0.8001	0.057*
C5	0.3988 (3)	0.1116 (2)	0.70940 (15)	0.0333 (4)
C6	0.4003 (3)	−0.0284 (2)	0.66182 (14)	0.0333 (4)
C7	0.2317 (3)	−0.0136 (2)	0.59585 (15)	0.0353 (5)
C8	0.0413 (3)	0.2804 (2)	0.63970 (15)	0.0338 (4)
C9	0.2282 (3)	0.2843 (2)	0.69348 (14)	0.0325 (4)
C10	0.3389 (4)	0.4169 (3)	0.61867 (18)	0.0478 (5)
H10A	0.4522	0.4298	0.6520	0.072*
H10B	0.2307	0.5261	0.6088	0.072*
H10C	0.4030	0.3776	0.5485	0.072*
C11	0.1267 (3)	0.3452 (3)	0.80564 (17)	0.0420 (5)
C12	−0.1109 (6)	0.3031 (5)	0.9735 (2)	0.0928 (10)
H12A	0.0009	0.2758	1.0194	0.111*	0.758 (6)
H12B	−0.1798	0.4266	0.9674	0.111*	0.758 (6)
H12C	−0.0798	0.2026	1.0286	0.111*	0.242 (6)
H12D	−0.0493	0.3888	0.9884	0.111*	0.242 (6)
C13	−0.2713 (9)	0.2137 (8)	1.0226 (3)	0.1076 (18)	0.758 (6)
H13A	−0.3858	0.2455	0.9791	0.161*	0.758 (6)
H13B	−0.3334	0.2432	1.0954	0.161*	0.758 (6)
H13C	−0.2036	0.0915	1.0268	0.161*	0.758 (6)
C13A	−0.340 (2)	0.371 (2)	0.9802 (11)	0.1076 (18)	0.242 (6)
H13D	−0.3722	0.4842	0.9389	0.161*	0.242 (6)
H13E	−0.4090	0.3774	1.0558	0.161*	0.242 (6)
H13F	−0.3969	0.2969	0.9504	0.161*	0.242 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0628 (10)	0.0400 (8)	0.0648 (10)	−0.0090 (7)	−0.0201 (8)	−0.0254 (7)
O2	0.0404 (9)	0.0454 (9)	0.0740 (10)	0.0051 (7)	−0.0223 (7)	−0.0247 (8)
O3	0.0921 (14)	0.0731 (11)	0.0728 (11)	−0.0273 (10)	−0.0124 (10)	−0.0462 (10)
O4	0.0681 (11)	0.0740 (11)	0.0415 (8)	−0.0234 (9)	0.0101 (7)	−0.0258 (8)
N1	0.0375 (10)	0.0385 (9)	0.0429 (9)	−0.0059 (7)	−0.0146 (7)	−0.0159 (7)
C1	0.0484 (13)	0.0332 (11)	0.0496 (12)	−0.0030 (9)	−0.0069 (10)	−0.0094 (9)
C2	0.0492 (14)	0.0422 (12)	0.0656 (15)	0.0057 (10)	−0.0151 (11)	−0.0057 (11)
C3	0.0463 (14)	0.0610 (15)	0.0650 (15)	−0.0035 (12)	−0.0275 (11)	−0.0035 (12)
C4	0.0460 (13)	0.0464 (12)	0.0569 (13)	−0.0082 (10)	−0.0224 (10)	−0.0133 (10)
C5	0.0323 (10)	0.0331 (10)	0.0342 (10)	−0.0069 (8)	−0.0043 (8)	−0.0089 (8)
C6	0.0351 (11)	0.0307 (10)	0.0323 (10)	−0.0078 (8)	−0.0024 (8)	−0.0062 (8)
C7	0.0385 (11)	0.0320 (10)	0.0371 (10)	−0.0104 (9)	−0.0027 (8)	−0.0114 (8)
C8	0.0323 (11)	0.0333 (10)	0.0367 (10)	−0.0072 (8)	−0.0050 (8)	−0.0112 (8)
C9	0.0329 (10)	0.0293 (9)	0.0380 (10)	−0.0073 (8)	−0.0070 (8)	−0.0116 (8)
C10	0.0494 (13)	0.0361 (11)	0.0607 (13)	−0.0152 (10)	−0.0107 (10)	−0.0058 (10)
C11	0.0405 (12)	0.0409 (11)	0.0459 (12)	−0.0019 (10)	−0.0133 (9)	−0.0168 (10)
C12	0.094 (2)	0.134 (3)	0.0461 (15)	−0.029 (2)	0.0168 (14)	−0.0391 (17)
C13	0.125 (4)	0.143 (5)	0.059 (3)	−0.068 (4)	0.035 (2)	−0.030 (3)
C13A	0.125 (4)	0.143 (5)	0.059 (3)	−0.068 (4)	0.035 (2)	−0.030 (3)

O1—C7	1.223 (2)	C6—C7	1.473 (3)
O2—C8	1.208 (2)	C8—C9	1.519 (3)
O3—C11	1.197 (2)	C9—C11	1.527 (3)
O4—C11	1.324 (3)	C9—C10	1.535 (3)
O4—C12	1.463 (3)	C10—H10A	0.9600
N1—C7	1.371 (2)	C10—H10B	0.9600
N1—C8	1.372 (2)	C10—H10C	0.9600
N1—H1	0.8600	C12—C13A	1.406 (13)
C1—C2	1.373 (3)	C12—C13	1.412 (5)
C1—C6	1.390 (3)	C12—H12A	0.9700
C1—H1A	0.9300	C12—H12B	0.9700
C2—C3	1.380 (3)	C12—H12C	0.9700
C2—H2	0.9300	C12—H12D	0.9700
C3—C4	1.376 (3)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.394 (3)	C13—H13C	0.9600
C4—H4	0.9300	C13A—H13D	0.9600
C5—C6	1.390 (2)	C13A—H13E	0.9600
C5—C9	1.517 (2)	C13A—H13F	0.9600
C11—O4—C12	115.2 (2)	C9—C10—H10C	109.5
C7—N1—C8	127.34 (15)	H10A—C10—H10C	109.5
C7—N1—H1	116.3	H10B—C10—H10C	109.5
C8—N1—H1	116.3	O3—C11—O4	124.5 (2)
C2—C1—C6	120.26 (19)	O3—C11—C9	123.9 (2)
C2—C1—H1A	119.9	O4—C11—C9	111.54 (16)
C6—C1—H1A	119.9	C13A—C12—C13	54.0 (7)
C1—C2—C3	119.5 (2)	C13A—C12—O4	110.5 (6)
C1—C2—H2	120.3	C13—C12—O4	110.2 (3)
C3—C2—H2	120.3	C13A—C12—H12A	139.8
C4—C3—C2	120.8 (2)	C13—C12—H12A	109.6
C4—C3—H3	119.6	O4—C12—H12A	109.6
C2—C3—H3	119.6	C13A—C12—H12B	58.6
C3—C4—C5	120.40 (19)	C13—C12—H12B	109.6
C3—C4—H4	119.8	O4—C12—H12B	109.6
C5—C4—H4	119.8	H12A—C12—H12B	108.1
C6—C5—C4	118.45 (18)	C13A—C12—H12C	109.5
C6—C5—C9	121.52 (16)	C13—C12—H12C	58.8
C4—C5—C9	119.93 (16)	O4—C12—H12C	109.5
C1—C6—C5	120.58 (18)	H12A—C12—H12C	54.2
C1—C6—C7	118.94 (17)	H12B—C12—H12C	140.7
C5—C6—C7	120.46 (16)	C13A—C12—H12D	109.5
O1—C7—N1	120.24 (17)	C13—C12—H12D	140.2
O1—C7—C6	122.58 (17)	O4—C12—H12D	109.5
N1—C7—C6	117.17 (15)	H12A—C12—H12D	56.7
O2—C8—N1	120.90 (17)	H12B—C12—H12D	54.3
O2—C8—C9	121.31 (15)	H12C—C12—H12D	108.1
N1—C8—C9	117.70 (15)	C12—C13—H13A	109.5
C5—C9—C8	114.29 (15)	C12—C13—H13B	109.5
C5—C9—C11	108.88 (15)	C12—C13—H13C	109.5
C8—C9—C11	107.75 (15)	C12—C13A—H13D	109.5
C5—C9—C10	109.59 (16)	C12—C13A—H13E	109.5
C8—C9—C10	106.40 (15)	H13D—C13A—H13E	109.5
C11—C9—C10	109.85 (16)	C12—C13A—H13F	109.5
C9—C10—H10A	109.5	H13D—C13A—H13F	109.5
C9—C10—H10B	109.5	H13E—C13A—H13F	109.5
H10A—C10—H10B	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.05	2.903 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.05	2.903 (3)	172

Symmetry code: (i) .