Ethyl 4-cyano-7-nitro-1,2,3,3a,4,5-hexa-hydro-pyrrolo-[1,2-a]quinoline-4-carboxyl-ate.

In the title compound, C(16)H(17)N(3)O(4), the six-membered N-containing ring adopts a half-chair conformation. One C atom of the five-membered ring is disordered over two sites, with occupancy factors of ca 0.67 and 0.33. The major pyrroline component adopts a half-chair conformation. Inter-molecular C-H⋯O hydrogen bonds forming centrosymmetric dimers are observed in the crystal.

Related literature

For the biological activity of tricyclic quinoline derivatives, see: Dalla Via et al. (2008 ▶); Gasparotto et al. (2006 ▶); Ferlin et al. (2000 ▶). For the crystal structure of an inter­mediate compound, see: Yapo, Konan et al. (2010 ▶). For a closely related crystal structure, see: Yapo, Abou et al. (2010 ▶). For ring conformation analysis, see: Cremer & Pople (1975 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H17N3O4

M = 315.33

Triclinic,

a = 7.2292 (2) Å

b = 9.1589 (3) Å

c = 11.8243 (5) Å

α = 79.332 (1)°

β = 82.609 (1)°

γ = 80.429 (2)°

V = 754.79 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 223 K

0.25 × 0.20 × 0.15 mm

Data collection

Nonius KappaCCD area-detector diffractometer

9677 measured reflections

3879 independent reflections

2498 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.247

S = 1.17

3879 reflections

214 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.75 e Å−3

Δρmin = −0.61 e Å−3

Data collection: COLLECT (Nonius, 2001 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812003480/wn2466sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003480/wn2466Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003480/wn2466Isup3.cml

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

C16H17N3O4	Z = 2
Mr = 315.33	F(000) = 332
Triclinic, P1	Dx = 1.387 Mg m−3
a = 7.2292 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1589 (3) Å	Cell parameters from 9677 reflections
c = 11.8243 (5) Å	θ = 1.8–29.2°
α = 79.332 (1)°	µ = 0.10 mm−1
β = 82.609 (1)°	T = 223 K
γ = 80.429 (2)°	Prism, yellow
V = 754.79 (5) Å3	0.25 × 0.20 × 0.15 mm

Nonius KappaCCD area-detector diffractometer	2498 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
graphite	θmax = 29.2°, θmin = 1.8°
φ and ω scans	h = 0→9
9677 measured reflections	k = −11→12
3879 independent reflections	l = −15→16

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)] = 0.083	H-atom parameters constrained
wR(F2) = 0.247	w = 1/[σ2(Fo2) + (0.1394P)2 + 0.0744P] where P = (Fo2 + 2Fc2)/3
S = 1.17	(Δ/σ)max < 0.001
3879 reflections	Δρmax = 0.75 e Å−3
214 parameters	Δρmin = −0.61 e Å−3
12 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.38 (4)

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)
N1	0.2977 (3)	0.58327 (19)	0.70594 (15)	0.0351 (5)
C1	0.2805 (3)	0.4588 (3)	0.80197 (18)	0.0412 (6)
H1A	0.3981	0.3908	0.8092	0.049*
H1B	0.1808	0.4032	0.7947	0.049*
C2A	0.2298 (6)	0.5486 (4)	0.9047 (3)	0.0419 (8)	0.672 (5)
H2A1	0.0953	0.5827	0.9146	0.050*	0.672 (5)
H2A2	0.2676	0.4865	0.9761	0.050*	0.672 (5)
C2B	0.3452 (12)	0.5011 (9)	0.9026 (6)	0.0419 (8)	0.328 (5)
H2B1	0.4735	0.4537	0.9134	0.050*	0.328 (5)
H2B2	0.2642	0.4719	0.9724	0.050*	0.328 (5)
C5	0.2756 (3)	0.5797 (2)	0.59352 (17)	0.0308 (5)
C8	0.2277 (3)	0.5789 (3)	0.36579 (18)	0.0367 (5)
O3	−0.0755 (2)	0.8596 (2)	0.64410 (15)	0.0488 (5)
C7	0.2484 (3)	0.7115 (3)	0.39876 (18)	0.0365 (5)
H7	0.2451	0.7994	0.3446	0.044*
C10	0.2506 (3)	0.4473 (2)	0.55766 (19)	0.0352 (5)
H10	0.2504	0.3591	0.6112	0.042*
C4	0.3558 (3)	0.7113 (2)	0.74133 (18)	0.0348 (5)
H4	0.4904	0.7105	0.7159	0.042*
C11	0.2999 (3)	0.8593 (2)	0.54725 (18)	0.0369 (5)
H11A	0.2216	0.9420	0.5043	0.044*
H11B	0.4302	0.8752	0.5273	0.044*
O4	−0.0134 (2)	0.8945 (2)	0.81674 (14)	0.0480 (5)
O1	0.1913 (3)	0.4596 (2)	0.21612 (16)	0.0595 (6)
C6	0.2741 (3)	0.7141 (2)	0.51212 (17)	0.0326 (5)
N2	0.2021 (3)	0.5793 (3)	0.24618 (17)	0.0465 (5)
O2	0.1926 (4)	0.6986 (2)	0.17861 (16)	0.0722 (7)
C12	0.2475 (3)	0.8588 (2)	0.67809 (17)	0.0332 (5)
C9	0.2265 (3)	0.4462 (3)	0.4446 (2)	0.0375 (5)
H9	0.2097	0.3582	0.4212	0.045*
C14	0.0328 (3)	0.8707 (2)	0.70870 (18)	0.0344 (5)
N3	0.3742 (3)	1.0864 (2)	0.72921 (19)	0.0522 (6)
C13	0.3147 (3)	0.9878 (3)	0.70977 (19)	0.0389 (5)
C3	0.3340 (4)	0.6763 (3)	0.8734 (2)	0.0485 (6)
H3A	0.4566	0.6512	0.9028	0.058*
H3B	0.2651	0.7623	0.9053	0.058*
C15	−0.2116 (4)	0.8961 (3)	0.8615 (2)	0.0541 (7)
H15A	−0.2559	0.8064	0.8495	0.065*
H15B	−0.2880	0.9831	0.8219	0.065*
C16	−0.2252 (5)	0.9021 (4)	0.9866 (3)	0.0725 (9)
H16A	−0.1379	0.8220	1.0232	0.109*
H16B	−0.3511	0.8914	1.0207	0.109*
H16C	−0.1953	0.9968	0.9969	0.109*

	U11	U22	U33	U12	U13	U23
N1	0.0446 (11)	0.0312 (9)	0.0282 (9)	−0.0060 (7)	−0.0043 (7)	−0.0011 (7)
C1	0.0448 (13)	0.0414 (12)	0.0345 (12)	−0.0088 (10)	−0.0089 (9)	0.0067 (9)
C2A	0.0446 (19)	0.0502 (19)	0.0286 (14)	−0.0076 (16)	−0.0043 (15)	0.0000 (13)
C2B	0.0446 (19)	0.0502 (19)	0.0286 (14)	−0.0076 (16)	−0.0043 (15)	0.0000 (13)
C5	0.0278 (10)	0.0339 (10)	0.0285 (10)	−0.0011 (8)	−0.0013 (8)	−0.0037 (8)
C8	0.0303 (11)	0.0500 (13)	0.0301 (11)	−0.0029 (9)	−0.0021 (8)	−0.0110 (9)
O3	0.0427 (10)	0.0580 (11)	0.0475 (10)	−0.0053 (8)	−0.0129 (8)	−0.0095 (8)
C7	0.0353 (11)	0.0414 (11)	0.0299 (11)	−0.0042 (9)	−0.0003 (8)	−0.0014 (8)
C10	0.0342 (11)	0.0329 (10)	0.0366 (11)	−0.0028 (8)	−0.0001 (9)	−0.0054 (8)
C4	0.0345 (11)	0.0350 (11)	0.0345 (11)	−0.0019 (8)	−0.0063 (8)	−0.0058 (8)
C11	0.0454 (12)	0.0344 (11)	0.0299 (11)	−0.0104 (9)	−0.0007 (9)	−0.0006 (8)
O4	0.0382 (9)	0.0667 (11)	0.0412 (9)	−0.0079 (8)	−0.0005 (7)	−0.0168 (8)
O1	0.0681 (13)	0.0687 (13)	0.0492 (11)	−0.0066 (10)	−0.0115 (9)	−0.0284 (9)
C6	0.0319 (10)	0.0356 (11)	0.0294 (10)	−0.0054 (8)	−0.0015 (8)	−0.0041 (8)
N2	0.0432 (11)	0.0633 (14)	0.0342 (10)	−0.0040 (10)	−0.0055 (8)	−0.0141 (9)
O2	0.1117 (19)	0.0696 (13)	0.0376 (11)	−0.0166 (12)	−0.0238 (11)	−0.0003 (9)
C12	0.0382 (11)	0.0316 (10)	0.0304 (10)	−0.0066 (8)	−0.0027 (8)	−0.0059 (8)
C9	0.0331 (11)	0.0392 (11)	0.0420 (12)	−0.0027 (9)	−0.0024 (9)	−0.0150 (9)
C14	0.0383 (11)	0.0293 (10)	0.0346 (11)	−0.0034 (8)	−0.0051 (9)	−0.0033 (8)
N3	0.0609 (14)	0.0443 (12)	0.0561 (14)	−0.0191 (10)	−0.0045 (10)	−0.0106 (10)
C13	0.0408 (12)	0.0392 (12)	0.0365 (12)	−0.0057 (9)	−0.0052 (9)	−0.0049 (9)
C3	0.0611 (16)	0.0466 (13)	0.0353 (12)	0.0052 (11)	−0.0143 (11)	−0.0053 (10)
C15	0.0392 (14)	0.0663 (17)	0.0566 (16)	−0.0072 (12)	0.0027 (11)	−0.0148 (13)
C16	0.0599 (19)	0.098 (2)	0.0578 (18)	−0.0145 (17)	0.0146 (14)	−0.0208 (17)

N1—C5	1.366 (3)	C4—C3	1.528 (3)
N1—C4	1.455 (3)	C4—C12	1.556 (3)
N1—C1	1.461 (3)	C4—H4	0.9800
C1—C2B	1.470 (7)	C11—C6	1.510 (3)
C1—C2A	1.562 (4)	C11—C12	1.544 (3)
C1—H1A	0.9700	C11—H11A	0.9700
C1—H1B	0.9700	C11—H11B	0.9700
C2A—C3	1.461 (4)	O4—C14	1.327 (3)
C2A—H2A1	0.9700	O4—C15	1.461 (3)
C2A—H2A2	0.9700	O1—N2	1.231 (3)
C2B—C3	1.568 (8)	N2—O2	1.226 (3)
C2B—H2B1	0.9700	C12—C13	1.475 (3)
C2B—H2B2	0.9700	C12—C14	1.538 (3)
C5—C10	1.402 (3)	C9—H9	0.9300
C5—C6	1.415 (3)	N3—C13	1.133 (3)
C8—C7	1.379 (3)	C3—H3A	0.9700
C8—C9	1.389 (3)	C3—H3B	0.9700
C8—N2	1.449 (3)	C15—C16	1.480 (4)
O3—C14	1.190 (3)	C15—H15A	0.9700
C7—C6	1.382 (3)	C15—H15B	0.9700
C7—H7	0.9300	C16—H16A	0.9600
C10—C9	1.373 (3)	C16—H16B	0.9600
C10—H10	0.9300	C16—H16C	0.9600
C5—N1—C4	122.46 (16)	C6—C11—H11B	109.2
C5—N1—C1	125.17 (17)	C12—C11—H11B	109.2
C4—N1—C1	112.23 (16)	H11A—C11—H11B	107.9
N1—C1—C2B	107.2 (3)	C14—O4—C15	116.71 (18)
N1—C1—C2A	99.7 (2)	C7—C6—C5	119.03 (19)
C2B—C1—C2A	33.3 (3)	C7—C6—C11	119.84 (18)
N1—C1—H1A	111.8	C5—C6—C11	121.13 (18)
C2B—C1—H1A	79.1	O2—N2—O1	122.4 (2)
C2A—C1—H1A	111.8	O2—N2—C8	118.9 (2)
N1—C1—H1B	111.8	O1—N2—C8	118.7 (2)
C2B—C1—H1B	132.2	C13—C12—C14	109.33 (18)
C2A—C1—H1B	111.8	C13—C12—C11	108.76 (17)
H1A—C1—H1B	109.6	C14—C12—C11	110.85 (17)
C3—C2A—C1	105.5 (2)	C13—C12—C4	108.75 (17)
C3—C2A—H2A1	110.6	C14—C12—C4	112.53 (16)
C1—C2A—H2A1	110.6	C11—C12—C4	106.51 (17)
C3—C2A—H2A2	110.6	C10—C9—C8	118.7 (2)
C1—C2A—H2A2	110.6	C10—C9—H9	120.6
H2A1—C2A—H2A2	108.8	C8—C9—H9	120.6
C1—C2B—C3	104.8 (5)	O3—C14—O4	125.2 (2)
C1—C2B—H2B1	110.8	O3—C14—C12	124.4 (2)
C3—C2B—H2B1	110.8	O4—C14—C12	110.42 (17)
C1—C2B—H2B2	110.8	N3—C13—C12	176.2 (3)
C3—C2B—H2B2	110.8	C2A—C3—C4	106.2 (2)
H2B1—C2B—H2B2	108.9	C2A—C3—C2B	33.3 (3)
N1—C5—C10	121.69 (18)	C4—C3—C2B	104.6 (3)
N1—C5—C6	118.85 (18)	C2A—C3—H3A	110.5
C10—C5—C6	119.45 (18)	C4—C3—H3A	110.5
C7—C8—C9	121.76 (19)	C2B—C3—H3A	80.7
C7—C8—N2	118.9 (2)	C2A—C3—H3B	110.5
C9—C8—N2	119.3 (2)	C4—C3—H3B	110.5
C8—C7—C6	120.1 (2)	C2B—C3—H3B	136.8
C8—C7—H7	119.9	H3A—C3—H3B	108.7
C6—C7—H7	119.9	O4—C15—C16	107.2 (2)
C9—C10—C5	120.9 (2)	O4—C15—H15A	110.3
C9—C10—H10	119.5	C16—C15—H15A	110.3
C5—C10—H10	119.5	O4—C15—H15B	110.3
N1—C4—C3	104.31 (17)	C16—C15—H15B	110.3
N1—C4—C12	109.20 (16)	H15A—C15—H15B	108.5
C3—C4—C12	119.69 (19)	C15—C16—H16A	109.5
N1—C4—H4	107.7	C15—C16—H16B	109.5
C3—C4—H4	107.7	H16A—C16—H16B	109.5
C12—C4—H4	107.7	C15—C16—H16C	109.5
C6—C11—C12	112.16 (16)	H16A—C16—H16C	109.5
C6—C11—H11A	109.2	H16B—C16—H16C	109.5
C12—C11—H11A	109.2
C5—N1—C1—C2B	170.8 (4)	C6—C11—C12—C13	167.79 (18)
C4—N1—C1—C2B	−4.9 (4)	C6—C11—C12—C14	−72.0 (2)
C5—N1—C1—C2A	−155.8 (2)	C6—C11—C12—C4	50.7 (2)
C4—N1—C1—C2A	28.5 (3)	N1—C4—C12—C13	−177.03 (18)
N1—C1—C2A—C3	−34.5 (3)	C3—C4—C12—C13	63.0 (3)
C2B—C1—C2A—C3	72.1 (6)	N1—C4—C12—C14	61.7 (2)
N1—C1—C2B—C3	19.3 (6)	C3—C4—C12—C14	−58.3 (3)
C2A—C1—C2B—C3	−62.0 (5)	N1—C4—C12—C11	−60.0 (2)
C4—N1—C5—C10	169.18 (19)	C3—C4—C12—C11	−179.95 (19)
C1—N1—C5—C10	−6.1 (3)	C5—C10—C9—C8	0.1 (3)
C4—N1—C5—C6	−12.2 (3)	C7—C8—C9—C10	−1.4 (3)
C1—N1—C5—C6	172.52 (19)	N2—C8—C9—C10	−179.92 (18)
C9—C8—C7—C6	1.8 (3)	C15—O4—C14—O3	4.6 (3)
N2—C8—C7—C6	−179.62 (19)	C15—O4—C14—C12	−175.16 (19)
N1—C5—C10—C9	179.25 (19)	C13—C12—C14—O3	130.1 (2)
C6—C5—C10—C9	0.6 (3)	C11—C12—C14—O3	10.2 (3)
C5—N1—C4—C3	172.03 (19)	C4—C12—C14—O3	−108.9 (2)
C1—N1—C4—C3	−12.1 (2)	C13—C12—C14—O4	−50.1 (2)
C5—N1—C4—C12	43.0 (3)	C11—C12—C14—O4	−169.98 (16)
C1—N1—C4—C12	−141.17 (18)	C4—C12—C14—O4	70.9 (2)
C8—C7—C6—C5	−1.0 (3)	C14—C12—C13—N3	−151 (4)
C8—C7—C6—C11	179.0 (2)	C11—C12—C13—N3	−29 (4)
N1—C5—C6—C7	−178.85 (19)	C4—C12—C13—N3	86 (4)
C10—C5—C6—C7	−0.2 (3)	C1—C2A—C3—C4	28.8 (3)
N1—C5—C6—C11	1.1 (3)	C1—C2A—C3—C2B	−63.2 (5)
C10—C5—C6—C11	179.78 (19)	N1—C4—C3—C2A	−11.4 (3)
C12—C11—C6—C7	157.10 (19)	C12—C4—C3—C2A	111.1 (3)
C12—C11—C6—C5	−22.9 (3)	N1—C4—C3—C2B	23.2 (4)
C7—C8—N2—O2	−2.7 (3)	C12—C4—C3—C2B	145.6 (4)
C9—C8—N2—O2	175.9 (2)	C1—C2B—C3—C2A	71.0 (6)
C7—C8—N2—O1	177.1 (2)	C1—C2B—C3—C4	−26.4 (6)
C9—C8—N2—O1	−4.3 (3)	C14—O4—C15—C16	172.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O3i	0.97	2.48	3.432 (3)	167.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O3i	0.97	2.48	3.432 (3)	167

Symmetry code: (i) .