Ethyl 4-cyano-7-nitro-1,2,3,3a,4,5-hexa­hydro­pyrrolo­[1,2-a]quinoline-4-carboxyl­ate

Bibila Mayaya Bisseyou, Y.; Timotou, A.; Adjou, A.; Kakou-Yao, R.; Tenon Abodou, J.

doi:10.1107/S1600536812003480

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o550-o551

doi:10.1107/S1600536812003480

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Ethyl 4-cyano-7-nitro-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoline-4-carboxylate

Yvon Bibila Mayaya Bisseyou,^a ^* Adéyolé Timotou,^b Ajouby Adjou,^b Rita Kakou-Yao ^a and Jules Tenon Abodou ^a

^aLaboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université de Cocody, 22 BP 582 Abidjan 22, Cote d'Ivoire, and ^bLaboratoire de Chimie Organique Structurale, UFR SSMT, Université de Cocody, 22 BP 582 Abidjan 22, Cote d'Ivoire
^*Correspondence e-mail: bibilamayayabisseyou@yahoo.fr

(Received 24 January 2012; accepted 26 January 2012; online 31 January 2012)

In the title compound, C₁₆H₁₇N₃O₄, 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. Intermolecular 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_r = 315.33
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.083
wR(F²) = 0.247
S = 1.17
3879 reflections
214 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.61 e Å⁻³

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) -x, -y+2, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812003480/wn2466sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812003480/wn2466Isup3.cml

checkCIF report

Comment top

The title compound is a tricyclic quinoline derivative obtained from an intermediate compound, (E)-ethyl 2-cyano-3-[5-nitro-2-(pyrrolidin-1-yl)phenyl]acrylate, whose molecular and crystal structures were recently determined by X-ray diffraction (Yapo, Konan et al., 2010). Tricyclic quinoline derivatives have received considerable attention because of their important therapeutic properties (Dalla Via et al., 2008; Gasparotto et al., 2006; Ferlin et al., 2000).

In this paper the crystal structure of the title compound is reported from single-crystal X-ray diffraction data collected at 223 K. The molecular structure of the title compound is shown in Fig. 1. The structure is composed of two principal parts: the quinoline ring system and the pyrroline ring.

The quinoline ring system has geometrical parameters which are consistent with those reported recently (Yapo, Abou et al., 2010). The six-membered N-containing ring adopts a half-chair conformation, with puckering parameters Q = 0.512 (2)Å, θ = 129.6 (2)°, ϕ = 283.6 (3)° (Cremer & Pople, 1975). The pyrroline ring exhibits disorder of atom C2 over two sites, with occupancy factors of 0.672 (5) and 0.328 (5). The major component of the five-membered ring adopts a half-chair conformation with puckering parameters Q(2) = 0.335 (3) Å and ϕ = 54.5 (5)° .

In the crystal structure, molecules form centrosymmetric dimeric units via C—H···O hydrogen bonds, characterized by an R²₂(10) (Bernstein et al., 1995) motif (Fig. 2). These centrosymmetric R²₂(10) dimers are arranged in the crystal structure as shown in Fig. 3.

Related literature top

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 top

(E)-Ethyl-2-cyano-3-(5-nitro-2-pyrrolidin-1-yl)phenyl) acrylate (2 g, 6.34 mmol) was dissolved in anhydrous dimethylformamide (10 ml). The mixture was heated to reflux over a period of 24 h. After cooling to ambient temperature, the reaction mixture was poured into water (20 ml). After extraction by ethyl acetate (2x50ml), the organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel. Elution solvent: hexane/ethyl acetate (90/10). Yellow single crystals of the title compound were obtained with a yield of 48% (m.p.: 397–398 K; Rf: 0.65, hexane/ethyl acetate: 90/10).

Computing details top

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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).

Figures top

	Fig. 1. ORTEP view of the molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radius. C2A and C2B are the major and minor components, respectively, of the disordered atom.
	Fig. 2. Part of the crystal packing showing a centrosymmetric R²₂(10) dimer unit. For the sake of clarity, the unit-cell outline and H atoms not involved in hydrogen bonds have been omitted. Dashed lines indicate hydrogen bonds. Atom O3a belongs to the molecule at symmetry position (-x+2,-y,-z+1).
	Fig. 3. Packing diagram of the title compound, viewed down the a axis. H atoms not involved in hydrogen bonds have been omitted for clarity. Dashed lines indicate hydrogen bonds.

Ethyl 4-cyano-7-nitro-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoline-4- carboxylate top

Crystal data top

C₁₆H₁₇N₃O₄	Z = 2
M_r = 315.33	F(000) = 332
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1394P)² + 0.0744P] where P = (F_o² + 2F_c²)/3
S = 1.17	(Δ/σ)_max < 0.001
3879 reflections	Δρ_max = 0.75 e Å⁻³
214 parameters	Δρ_min = −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)

Crystal data top

C₁₆H₁₇N₃O₄	γ = 80.429 (2)°
M_r = 315.33	V = 754.79 (5) Å³
Triclinic, P1	Z = 2
a = 7.2292 (2) Å	Mo Kα radiation
b = 9.1589 (3) Å	µ = 0.10 mm⁻¹
c = 11.8243 (5) Å	T = 223 K
α = 79.332 (1)°	0.25 × 0.20 × 0.15 mm
β = 82.609 (1)°

Data collection top

Nonius KappaCCD area-detector diffractometer	2498 reflections with I > 2σ(I)
9677 measured reflections	R_int = 0.049
3879 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.083	12 restraints
wR(F²) = 0.247	H-atom parameters constrained
S = 1.17	Δρ_max = 0.75 e Å⁻³
3879 reflections	Δρ_min = −0.61 e Å⁻³
214 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇N₃O₄
M_r	315.33
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	7.2292 (2), 9.1589 (3), 11.8243 (5)
α, β, γ (°)	79.332 (1), 82.609 (1), 80.429 (2)
V (Å³)	754.79 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9677, 3879, 2498
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.083, 0.247, 1.17
No. of reflections	3879
No. of parameters	214
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.61

Computer programs: COLLECT (Nonius, 2001), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O3ⁱ	0.97	2.48	3.432 (3)	166.6

Symmetry code: (i) −x, −y+2, −z+1.

Acknowledgements

The authors thank Michel Giorgi and the Spectropole Service, Faculty of Sciences and Techniques, Saint Jérome University, France, for the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
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Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 68| Part 2| February 2012| Pages o550-o551

doi:10.1107/S1600536812003480

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 4-cyano-7-nitro-1,2,3,3a,4,5-hexa­hydro­pyrrolo­[1,2-a]quinoline-4-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 4-cyano-7-nitro-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinoline-4-carboxylate