Methyl 4-methyl-2-oxo-1,2,5,6-tetra-hydro-4H-pyrrolo[3,2,1-ij]quinoline-6-carboxyl-ate.

In the title mol-ecule, C(14)H(15)NO(3), the six-membered heterocyclic ring exhibits an envelope conformation. In the crystal, C-H⋯π inter-actions link the mol-ecules into centrosymmetric dimers, and weak inter-molecular C-H⋯O hydrogen bonds link these dimers into columns propagated along [100].

Related literature

For details of the synthesis, see: Zhuravleva et al. (2009 ▶). For a related structure, see: Bond et al. (1979 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C14H15NO3

M = 245.27

Monoclinic,

a = 8.309 (3) Å

b = 18.524 (5) Å

c = 8.730 (3) Å

β = 112.30 (3)°

V = 1243.2 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.20 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

2699 measured reflections

2445 independent reflections

1974 reflections with I > 2σ(I)

R int = 0.030

1 standard reflections frequency: 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.174

S = 1.09

2445 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029948/cv2589sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029948/cv2589Isup2.hkl

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

C14H15NO3	F(000) = 520
Mr = 245.27	Dx = 1.310 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.309 (3) Å	θ = 19.8–20.5°
b = 18.524 (5) Å	µ = 0.09 mm−1
c = 8.730 (3) Å	T = 295 K
β = 112.30 (3)°	Prism, yellow
V = 1243.2 (8) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.030
Radiation source: Fine-focus sealed tube	θmax = 26.0°, θmin = 2.2°
Graphite	h = −10→9
Nonprofiled ω scans	k = 0→22
2699 measured reflections	l = 0→10
2445 independent reflections	1 standard reflections every 60 min
1974 reflections with I > 2σ(I)	intensity decay: 2%

Refinement on F2	Primary atom site location: Direct
Least-squares matrix: Full	Secondary atom site location: Difmap
R[F2 > 2σ(F2)] = 0.048	Hydrogen site location: Geom
wR(F2) = 0.174	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.1046P)2 + 0.277P] where P = (Fo2 + 2Fc2)/3
2445 reflections	(Δ/σ)max = 0.003
165 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N1	0.1569 (2)	0.42646 (8)	0.3299 (2)	0.0427 (4)
C2	0.1249 (3)	0.35798 (10)	0.3939 (2)	0.0465 (5)
H2	0.2271	0.3470	0.4937	0.056*
C21	0.1052 (3)	0.29783 (11)	0.2711 (3)	0.0580 (6)
H21A	−0.0013	0.3043	0.1768	0.087*
H21B	0.1027	0.2522	0.3223	0.087*
H21C	0.2016	0.2988	0.2360	0.087*
C3	−0.0291 (3)	0.36744 (11)	0.4463 (2)	0.0475 (5)
H3A	0.0069	0.3977	0.5443	0.057*
H3B	−0.0600	0.3206	0.4765	0.057*
C4	−0.1924 (3)	0.40114 (11)	0.3133 (2)	0.0453 (5)
H4	−0.2691	0.4158	0.3697	0.054*
C41	−0.2951 (3)	0.34861 (11)	0.1782 (3)	0.0505 (5)
O41	−0.3534 (3)	0.36109 (10)	0.0332 (2)	0.0836 (6)
O42	−0.3192 (2)	0.28667 (8)	0.2428 (2)	0.0678 (5)
C43	−0.4180 (4)	0.23173 (15)	0.1274 (4)	0.0925 (10)
H43A	−0.5231	0.2525	0.0496	0.139*
H43B	−0.4466	0.1935	0.1869	0.139*
H43C	−0.3499	0.2128	0.0691	0.139*
C5	−0.1448 (2)	0.46862 (10)	0.2453 (2)	0.0407 (4)
C6	−0.2560 (3)	0.52609 (12)	0.1702 (3)	0.0554 (6)
H6	−0.3722	0.5238	0.1578	0.067*
C7	−0.1959 (3)	0.58653 (12)	0.1140 (3)	0.0630 (7)
H7	−0.2727	0.6239	0.0642	0.076*
C8	−0.0246 (3)	0.59218 (11)	0.1306 (2)	0.0557 (6)
H8	0.0139	0.6327	0.0917	0.067*
C9	0.0883 (3)	0.53697 (10)	0.2055 (2)	0.0443 (5)
C10	0.0247 (2)	0.47699 (9)	0.2586 (2)	0.0362 (4)
C11	0.2786 (3)	0.52466 (12)	0.2464 (3)	0.0558 (6)
H11A	0.3485	0.5608	0.3233	0.067*
H11B	0.3050	0.5256	0.1473	0.067*
C12	0.3104 (3)	0.45028 (12)	0.3248 (3)	0.0521 (5)
O12	0.4456 (2)	0.41618 (10)	0.3776 (3)	0.0769 (6)

	U11	U22	U33	U12	U13	U23
N1	0.0376 (8)	0.0402 (9)	0.0496 (9)	0.0039 (6)	0.0159 (7)	0.0012 (7)
C2	0.0446 (10)	0.0439 (11)	0.0427 (10)	0.0043 (8)	0.0071 (8)	0.0094 (8)
C21	0.0725 (15)	0.0358 (10)	0.0690 (14)	0.0055 (10)	0.0308 (12)	−0.0003 (9)
C3	0.0561 (12)	0.0499 (11)	0.0356 (9)	−0.0064 (9)	0.0164 (8)	0.0018 (8)
C4	0.0408 (10)	0.0489 (11)	0.0491 (11)	−0.0034 (8)	0.0203 (8)	−0.0069 (8)
C41	0.0396 (10)	0.0497 (12)	0.0563 (13)	−0.0070 (8)	0.0115 (9)	−0.0031 (9)
O41	0.0950 (14)	0.0728 (12)	0.0569 (11)	−0.0272 (10)	−0.0007 (9)	−0.0017 (9)
O42	0.0704 (11)	0.0501 (9)	0.0745 (11)	−0.0186 (8)	0.0183 (9)	−0.0025 (8)
C43	0.0841 (19)	0.0559 (15)	0.111 (2)	−0.0299 (14)	0.0071 (17)	−0.0089 (15)
C5	0.0384 (9)	0.0415 (10)	0.0374 (9)	0.0009 (7)	0.0090 (7)	−0.0070 (7)
C6	0.0436 (11)	0.0502 (12)	0.0577 (13)	0.0093 (9)	0.0026 (9)	−0.0108 (10)
C7	0.0725 (16)	0.0412 (11)	0.0519 (13)	0.0150 (10)	−0.0029 (11)	−0.0007 (9)
C8	0.0873 (17)	0.0346 (10)	0.0378 (10)	−0.0015 (10)	0.0154 (10)	0.0016 (8)
C9	0.0595 (12)	0.0382 (10)	0.0371 (9)	−0.0051 (8)	0.0203 (9)	−0.0064 (7)
C10	0.0413 (10)	0.0335 (9)	0.0320 (8)	0.0013 (7)	0.0119 (7)	−0.0033 (7)
C11	0.0624 (14)	0.0507 (12)	0.0648 (13)	−0.0134 (10)	0.0358 (11)	−0.0086 (10)
C12	0.0427 (11)	0.0525 (12)	0.0652 (13)	−0.0049 (9)	0.0251 (10)	−0.0103 (10)
O12	0.0426 (9)	0.0747 (12)	0.1144 (15)	0.0075 (8)	0.0308 (9)	−0.0048 (10)

N1—C12	1.366 (3)	C43—H43A	0.9600
N1—C10	1.397 (2)	C43—H43B	0.9600
N1—C2	1.451 (2)	C43—H43C	0.9600
C2—C21	1.512 (3)	C5—C10	1.377 (3)
C2—C3	1.523 (3)	C5—C6	1.399 (3)
C2—H2	0.9800	C6—C7	1.389 (4)
C21—H21A	0.9600	C6—H6	0.9300
C21—H21B	0.9600	C7—C8	1.379 (4)
C21—H21C	0.9600	C7—H7	0.9300
C3—C4	1.544 (3)	C8—C9	1.374 (3)
C3—H3A	0.9700	C8—H8	0.9300
C3—H3B	0.9700	C9—C10	1.383 (3)
C4—C5	1.500 (3)	C9—C11	1.501 (3)
C4—C41	1.517 (3)	C11—C12	1.517 (3)
C4—H4	0.9800	C11—H11A	0.9700
C41—O41	1.193 (3)	C11—H11B	0.9700
C41—O42	1.327 (3)	C12—O12	1.217 (3)
O42—C43	1.449 (3)
C12—N1—C10	110.78 (17)	O42—C43—H43B	109.5
C12—N1—C2	127.21 (17)	H43A—C43—H43B	109.5
C10—N1—C2	121.98 (16)	O42—C43—H43C	109.5
N1—C2—C21	110.93 (17)	H43A—C43—H43C	109.5
N1—C2—C3	108.22 (16)	H43B—C43—H43C	109.5
C21—C2—C3	114.86 (18)	C10—C5—C6	115.24 (19)
N1—C2—H2	107.5	C10—C5—C4	118.39 (16)
C21—C2—H2	107.5	C6—C5—C4	126.37 (19)
C3—C2—H2	107.5	C7—C6—C5	121.1 (2)
C2—C21—H21A	109.5	C7—C6—H6	119.4
C2—C21—H21B	109.5	C5—C6—H6	119.4
H21A—C21—H21B	109.5	C8—C7—C6	121.3 (2)
C2—C21—H21C	109.5	C8—C7—H7	119.4
H21A—C21—H21C	109.5	C6—C7—H7	119.4
H21B—C21—H21C	109.5	C9—C8—C7	119.0 (2)
C2—C3—C4	114.81 (16)	C9—C8—H8	120.5
C2—C3—H3A	108.6	C7—C8—H8	120.5
C4—C3—H3A	108.6	C8—C9—C10	118.6 (2)
C2—C3—H3B	108.6	C8—C9—C11	133.9 (2)
C4—C3—H3B	108.6	C10—C9—C11	107.45 (17)
H3A—C3—H3B	107.5	C5—C10—C9	124.77 (17)
C5—C4—C41	112.46 (17)	C5—C10—N1	124.60 (17)
C5—C4—C3	110.24 (15)	C9—C10—N1	110.62 (17)
C41—C4—C3	113.57 (17)	C9—C11—C12	103.46 (16)
C5—C4—H4	106.7	C9—C11—H11A	111.1
C41—C4—H4	106.7	C12—C11—H11A	111.1
C3—C4—H4	106.7	C9—C11—H11B	111.1
O41—C41—O42	123.5 (2)	C12—C11—H11B	111.1
O41—C41—C4	125.6 (2)	H11A—C11—H11B	109.0
O42—C41—C4	110.80 (19)	O12—C12—N1	124.0 (2)
C41—O42—C43	116.7 (2)	O12—C12—C11	128.3 (2)
O42—C43—H43A	109.5	N1—C12—C11	107.66 (18)
C12—N1—C2—C21	−78.4 (3)	C7—C8—C9—C10	1.3 (3)
C10—N1—C2—C21	99.7 (2)	C7—C8—C9—C11	−179.1 (2)
C12—N1—C2—C3	154.76 (19)	C6—C5—C10—C9	0.7 (3)
C10—N1—C2—C3	−27.2 (2)	C4—C5—C10—C9	−178.29 (17)
N1—C2—C3—C4	51.5 (2)	C6—C5—C10—N1	179.68 (17)
C21—C2—C3—C4	−73.1 (2)	C4—C5—C10—N1	0.7 (3)
C2—C3—C4—C5	−50.2 (2)	C8—C9—C10—C5	−1.4 (3)
C2—C3—C4—C41	77.1 (2)	C11—C9—C10—C5	178.81 (17)
C5—C4—C41—O41	−9.3 (3)	C8—C9—C10—N1	179.47 (16)
C3—C4—C41—O41	−135.4 (3)	C11—C9—C10—N1	−0.3 (2)
C5—C4—C41—O42	173.46 (17)	C12—N1—C10—C5	−179.89 (17)
C3—C4—C41—O42	47.4 (2)	C2—N1—C10—C5	1.8 (3)
O41—C41—O42—C43	1.8 (4)	C12—N1—C10—C9	−0.8 (2)
C4—C41—O42—C43	179.1 (2)	C2—N1—C10—C9	−179.16 (16)
C41—C4—C5—C10	−105.06 (19)	C8—C9—C11—C12	−178.6 (2)
C3—C4—C5—C10	22.8 (2)	C10—C9—C11—C12	1.1 (2)
C41—C4—C5—C6	76.1 (2)	C10—N1—C12—O12	−179.4 (2)
C3—C4—C5—C6	−156.10 (19)	C2—N1—C12—O12	−1.1 (4)
C10—C5—C6—C7	0.1 (3)	C10—N1—C12—C11	1.5 (2)
C4—C5—C6—C7	179.04 (19)	C2—N1—C12—C11	179.75 (18)
C5—C6—C7—C8	−0.2 (3)	C9—C11—C12—O12	179.4 (2)
C6—C7—C8—C9	−0.5 (3)	C9—C11—C12—N1	−1.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cgi	0.97	2.55	3.514 (3)	174
C4—H4···O12ii	0.98	2.40	3.274 (3)	149
C11—H11A···O12iii	0.97	2.56	3.394 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯Cgi	0.97	2.55	3.514 (3)	174
C4—H4⋯O12ii	0.98	2.40	3.274 (3)	149
C11—H11A⋯O12iii	0.97	2.56	3.394 (3)	145

Symmetry codes: (i) ; (ii) ; (iii) . Cg is the centroid of the C5–C10 ring.