Ethyl 5-cyano-8-nitro-2,3,4,4a,5,6-hexahydro-1H-pyrido[1,2-a]quinoline-5-carboxylate

Yapo, Y.M.; Konan, K.M.; Adjou, A.; Timotou, A.; Tenon, J.A.

doi:10.1107/S160053681002283X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1735

doi:10.1107/S160053681002283X

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Ethyl 5-cyano-8-nitro-2,3,4,4a,5,6-hexahydro-1H-pyrido[1,2-a]quinoline-5-carboxylate

Yapi Marcellin Yapo,^a ^* Kouakou Michel Konan,^a Ané Adjou,^b Adéyolé Timotou ^b and Jules A. Tenon ^a

^aLaboratoire de Cristallographie et Physique Moléculaire, UFR–SSMT, Université de Cocody, 22 BP 582 Abidjan 22, Côte d'Ivoire, and ^bLaboratoire de Chimie Organique Structurale, UFR–SSMT, Université de Cocody, 22 BP 582 Abidjan 22, Côte d'Ivoire
^*Correspondence e-mail: marcellin.yapo@univ-cocody.ci

(Received 27 May 2010; accepted 14 June 2010; online 23 June 2010)

In the title compound, C₁₇H₁₉N₃O₄, the piperidine ring adopts a chair conformation. The crystal structure features inversion dimers linked by pairs of weak C—H⋯N hydrogen bonds.

Related literature

For the therapeutic properties of quinoline derivatives, see: Dalla Via et al. (2008 ); Gasparotto et al. (2006 ); Ferlin et al. (2000 ). A similar heterocyclic structure, Mitomycin C, is used in cancer therapy, see: Crooke & Bradner (1976 ); Danishefsky & Ciufolini (1984 ); Remers (1980 ). For related structures, see: Zhuravleva et al. (2009 ); Oliveira et al. (2006 ). For ring conformation analysis, see: Cremer & Pople (1975 ). For reference bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₇H₁₉N₃O₄
M_r = 329.36
Triclinic, $[P \overline 1]$
a = 8.8257 (4) Å
b = 9.2256 (5) Å
c = 10.5011 (6) Å
α = 88.246 (4)°
β = 75.089 (2)°
γ = 83.289 (3)°
V = 820.57 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 223 K
0.20 × 0.20 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer
10064 measured reflections
4189 independent reflections
2794 reflections with I > 2σ(I)
R_int = 0.04

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.096
S = 1.04
2503 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H72⋯N3ⁱ	0.97	2.56	3.492 (3)	161
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: COLLECT (Nonius, 2001 ); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: CRYSTALS.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002283X/bq2218sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681002283X/bq2218Isup2.hkl

checkCIF report

Comment top

Tricyclic quinoline derivatives have diverse and important therapeutic properties (Dalla Via et al., 2008; Gasparotto et al., 2006; Ferlin et al., 2000). These heterocyclic are similar to Mitomycin C which is a powerful antibiotic used in cancerous chemotherapy (Crooke et al., 1976; Remers et al., 1980; Danishefsky et al., 1984). They are also used as intermediate compound to elaborate keratic fiber colorings. Here, we report the single X-ray determination of the title compound C₁₇H₁₉N₃O₄, (I), in order to have a best insight of its structure and then to undertake a study of its possible therapeutic activity. The molecular structure of this compound and its atomic labeling scheme are shown in Figure 1. The bond lenghts distances are within the accepted range (Allen et al., 1987). In (I), there are two coupled rings: quinoline and piperidine rings. The geometrical characteristics relating bond distances in quinoline ring are consistent and present no particularity with the recently reported (Oliveira et al., 2006; Zhuravleva et al., 2009). By least squares planes method, it is observed that carbon atom C8 deviates of -0.4074Å to quinoline cycle plane what proves that quinoline ring is not veritably plane. Concerning piperidine ring, it assumes a chair conformation which the puckering parameters (Cremer & Pople, 1975): θ=7.78°, Q=0.6147Å and Φ=42.46°. The crystal packing is due to the weak hydrogen bonds C-H···N which ensure crystal cohesion (Table 1 and Figure 2).

Related literature top

For the therapeutic properties of quinoline derivatives, see: Dalla Via et al. (2008); Gasparotto et al. (2006); Ferlin et al. (2000). For related structures, see: Zhuravleva et al. (2009); Oliveira et al. (2006). For ring conformation analysis, see: Cremer & Pople (1975). For reference bond lengths, see: Allen et al. (1987).

For related literature, see: Crooke & Bradner (1976); Danishefsky & Ciufolini (1984); Remers (1980).

Experimental top

3.5 g, 10 mmol of malonic arylidene was dissolved in 10 ml of dimethylformamide. The melange was heated to reflux during 24 h. After cooling to ambient temperature, 20 ml of water was added to the melange. After extraction to ethyl acetate (150 ml), the organic layers were dried on magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using hexane/ethyl acetate (80/20) to obtain yellow crystals with 45% yields. The melting point is 424 K

Computing details top

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top

	Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The crystal packing of (I). Hydrogen bonds C-H···N are shown as dashes lines: Symmetry code : (i) -x+1, -y+1, -z+1.

Ethyl 5-cyano-8-nitro-2,3,4,4a,5,6-hexahydro- 1H-pyrido[1,2-a]quinoline-5-carboxylate top

Crystal data top

C₁₇H₁₉N₃O₄	Z = 2
M_r = 329.36	F(000) = 348
Triclinic, P1	D_x = 1.333 Mg m⁻³
Hall symbol: -P 1	Melting point: 424 K
a = 8.8257 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2256 (5) Å	Cell parameters from 10064 reflections
c = 10.5011 (6) Å	θ = 2–29°
α = 88.246 (4)°	µ = 0.10 mm⁻¹
β = 75.089 (2)°	T = 223 K
γ = 83.289 (3)°	Prism, yellow
V = 820.57 (8) Å³	0.20 × 0.20 × 0.20 mm

Data collection top

Nonius KappaCCD diffractometer	R_int = 0.04
Graphite monochromator	θ_max = 29.1°, θ_min = 2.0°
ϕ and ω scans	h = 0→12
10064 measured reflections	k = −11→12
4189 independent reflections	l = −13→14
2794 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F²) + (0.02P)² + 0.5P], where P = (max(F_o²,0) + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.000163
2503 reflections	Δρ_max = 0.21 e Å⁻³
217 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints

Crystal data top

C₁₇H₁₉N₃O₄	γ = 83.289 (3)°
M_r = 329.36	V = 820.57 (8) Å³
Triclinic, P1	Z = 2
a = 8.8257 (4) Å	Mo Kα radiation
b = 9.2256 (5) Å	µ = 0.10 mm⁻¹
c = 10.5011 (6) Å	T = 223 K
α = 88.246 (4)°	0.20 × 0.20 × 0.20 mm
β = 75.089 (2)°

Data collection top

Nonius KappaCCD diffractometer	2794 reflections with I > 2σ(I)
10064 measured reflections	R_int = 0.04
4189 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	Δρ_max = 0.21 e Å⁻³
2503 reflections	Δρ_min = −0.26 e Å⁻³
217 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.70920 (19)	0.86006 (18)	0.50748 (17)	0.0241
N1	0.70324 (17)	0.85963 (14)	0.63954 (14)	0.0268
O3	0.66155 (17)	0.46173 (14)	0.84947 (13)	0.0393
C9	0.7451 (2)	0.72488 (18)	0.70764 (17)	0.0256
C2	0.6873 (2)	0.99129 (19)	0.43830 (18)	0.0287
C6	0.7271 (2)	0.72669 (18)	0.43802 (17)	0.0269
C5	0.7160 (2)	0.72795 (19)	0.30929 (18)	0.0308
C4	0.6920 (2)	0.8595 (2)	0.24574 (17)	0.0311
O4	0.8187 (2)	0.35165 (15)	0.66714 (15)	0.0548
O2	0.6821 (2)	0.74186 (19)	0.05771 (16)	0.0639
C3	0.6790 (2)	0.99068 (19)	0.30939 (18)	0.0308
C7	0.7604 (2)	0.58338 (19)	0.50323 (18)	0.0325
C8	0.6879 (2)	0.59435 (18)	0.65159 (17)	0.0278
C10	0.9210 (2)	0.7072 (2)	0.70064 (19)	0.0327
N3	0.3802 (2)	0.63652 (18)	0.69548 (19)	0.0450
N2	0.6797 (2)	0.8591 (2)	0.11110 (17)	0.0436
O1	0.6673 (2)	0.97711 (19)	0.05381 (15)	0.0652
C13	0.7303 (2)	0.98771 (19)	0.70769 (18)	0.0310
C17	0.5143 (2)	0.61781 (18)	0.67811 (19)	0.0322
C12	0.9039 (2)	0.9820 (2)	0.70523 (19)	0.0346
C14	0.7321 (2)	0.45278 (19)	0.72194 (19)	0.0328
C11	0.9606 (2)	0.8393 (2)	0.7643 (2)	0.0358
C15	0.6946 (3)	0.3372 (2)	0.9327 (2)	0.0461
C16	0.8465 (4)	0.3441 (3)	0.9667 (3)	0.0711
H91	0.6874	0.7364	0.8009	0.0307*
H51	0.7270	0.6393	0.2640	0.0374*
H31	0.6639	1.0787	0.2640	0.0358*
H71	0.8751	0.5568	0.4875	0.0395*
H72	0.7193	0.5065	0.4655	0.0388*
H101	0.9454	0.6173	0.7460	0.0386*
H102	0.9806	0.7000	0.6083	0.0399*
H122	0.9191	1.0653	0.7543	0.0424*
H121	0.9656	0.9890	0.6138	0.0425*
H112	1.0737	0.8312	0.7531	0.0436*
H111	0.9082	0.8405	0.8586	0.0444*
H152	0.6075	0.3476	1.0124	0.0547*
H151	0.6960	0.2467	0.8845	0.0545*
H162	0.8619	0.2658	1.0269	0.0858*
H161	0.8453	0.4366	1.0086	0.0858*
H163	0.9346	0.3328	0.8875	0.0858*
H21	0.6783	1.0810	0.4814	0.0340*
H131	0.6679	0.9883	0.7985	0.0380*
H132	0.6990	1.0760	0.6639	0.0380*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0202 (8)	0.0264 (9)	0.0259 (9)	−0.0011 (6)	−0.0068 (7)	−0.0010 (7)
N1	0.0338 (9)	0.0213 (7)	0.0269 (8)	0.0003 (6)	−0.0122 (7)	−0.0028 (6)
O3	0.0480 (9)	0.0337 (7)	0.0313 (8)	0.0038 (6)	−0.0057 (6)	0.0066 (6)
C9	0.0293 (9)	0.0242 (8)	0.0237 (9)	−0.0009 (7)	−0.0087 (7)	0.0007 (7)
C2	0.0264 (9)	0.0269 (9)	0.0316 (10)	−0.0020 (7)	−0.0061 (8)	0.0012 (7)
C6	0.0268 (9)	0.0274 (9)	0.0258 (9)	−0.0008 (7)	−0.0066 (7)	0.0000 (7)
C5	0.0332 (10)	0.0331 (10)	0.0262 (9)	−0.0035 (8)	−0.0076 (8)	−0.0024 (7)
C4	0.0301 (10)	0.0422 (11)	0.0206 (9)	−0.0055 (8)	−0.0058 (7)	0.0036 (7)
O4	0.0801 (12)	0.0323 (8)	0.0403 (9)	0.0185 (8)	−0.0056 (8)	0.0011 (6)
O2	0.0985 (15)	0.0666 (11)	0.0350 (9)	−0.0240 (10)	−0.0255 (9)	−0.0007 (8)
C3	0.0245 (9)	0.0345 (10)	0.0313 (10)	−0.0025 (7)	−0.0048 (8)	0.0086 (8)
C7	0.0452 (11)	0.0265 (9)	0.0259 (10)	0.0021 (8)	−0.0115 (9)	−0.0037 (7)
C8	0.0326 (10)	0.0233 (9)	0.0276 (10)	0.0006 (7)	−0.0097 (8)	0.0001 (7)
C10	0.0302 (10)	0.0314 (10)	0.0361 (11)	0.0007 (8)	−0.0101 (8)	0.0039 (8)
N3	0.0402 (11)	0.0384 (10)	0.0596 (12)	−0.0061 (8)	−0.0174 (9)	−0.0034 (8)
N2	0.0455 (11)	0.0574 (12)	0.0267 (9)	−0.0062 (9)	−0.0076 (8)	0.0059 (8)
O1	0.0931 (14)	0.0654 (11)	0.0342 (9)	0.0056 (10)	−0.0195 (9)	0.0154 (8)
C13	0.0372 (11)	0.0257 (9)	0.0320 (10)	−0.0002 (8)	−0.0132 (8)	−0.0046 (7)
C17	0.0422 (12)	0.0223 (9)	0.0349 (10)	−0.0051 (8)	−0.0141 (9)	−0.0009 (7)
C12	0.0362 (11)	0.0338 (10)	0.0358 (11)	−0.0078 (8)	−0.0110 (9)	−0.0017 (8)
C14	0.0400 (11)	0.0265 (9)	0.0321 (10)	−0.0015 (8)	−0.0105 (9)	0.0009 (8)
C11	0.0282 (10)	0.0431 (11)	0.0378 (11)	−0.0062 (8)	−0.0108 (8)	0.0019 (9)
C15	0.0573 (14)	0.0401 (12)	0.0364 (12)	0.0018 (10)	−0.0088 (10)	0.0141 (9)
C16	0.0735 (19)	0.086 (2)	0.0595 (17)	−0.0018 (15)	−0.0330 (15)	0.0224 (14)

Geometric parameters (Å, º) top

C1—N1	1.374 (2)	C7—H72	0.971
C1—C2	1.412 (2)	C8—C17	1.476 (3)
C1—C6	1.422 (2)	C8—C14	1.541 (2)
N1—C9	1.472 (2)	C10—C11	1.525 (3)
N1—C13	1.474 (2)	C10—H101	0.973
O3—C14	1.324 (2)	C10—H102	0.977
O3—C15	1.469 (2)	N3—C17	1.143 (2)
C9—C8	1.546 (2)	N2—O1	1.235 (2)
C9—C10	1.524 (3)	C13—C12	1.520 (3)
C9—H91	0.983	C13—H131	0.970
C2—C3	1.375 (3)	C13—H132	0.970
C2—H21	0.941	C12—C11	1.524 (3)
C6—C5	1.380 (2)	C12—H122	0.979
C6—C7	1.504 (2)	C12—H121	0.979
C5—C4	1.388 (3)	C11—H112	0.969
C5—H51	0.941	C11—H111	0.979
C4—C3	1.379 (3)	C15—C16	1.482 (4)
C4—N2	1.446 (2)	C15—H152	0.979
O4—C14	1.194 (2)	C15—H151	0.987
O2—N2	1.229 (2)	C16—H162	0.966
C3—H31	0.942	C16—H161	0.969
C7—C8	1.526 (2)	C16—H163	0.980
C7—H71	0.985

N1—C1—C2	121.61 (15)	C11—C10—H101	111.3
N1—C1—C6	120.57 (15)	C9—C10—H102	109.0
C2—C1—C6	117.69 (16)	C11—C10—H102	109.9
C1—N1—C9	121.40 (13)	H101—C10—H102	109.1
C1—N1—C13	122.69 (14)	C4—N2—O2	119.05 (17)
C9—N1—C13	109.99 (13)	C4—N2—O1	118.60 (18)
C14—O3—C15	117.40 (15)	O2—N2—O1	122.36 (18)
N1—C9—C8	109.45 (14)	N1—C13—C12	110.21 (14)
N1—C9—C10	110.06 (14)	N1—C13—H131	109.3
C8—C9—C10	114.36 (14)	C12—C13—H131	109.3
N1—C9—H91	107.0	N1—C13—H132	109.3
C8—C9—H91	108.0	C12—C13—H132	109.3
C10—C9—H91	107.7	H131—C13—H132	109.4
C1—C2—C3	121.40 (16)	C8—C17—N3	178.4 (2)
C1—C2—H21	119.3	C13—C12—C11	110.80 (15)
C3—C2—H21	119.3	C13—C12—H122	109.2
C1—C6—C5	120.13 (16)	C11—C12—H122	110.4
C1—C6—C7	120.45 (15)	C13—C12—H121	109.0
C5—C6—C7	119.41 (15)	C11—C12—H121	109.0
C6—C5—C4	120.19 (16)	H122—C12—H121	108.5
C6—C5—H51	119.8	C8—C14—O3	110.12 (15)
C4—C5—H51	120.0	C8—C14—O4	123.73 (18)
C5—C4—C3	120.93 (17)	O3—C14—O4	126.15 (17)
C5—C4—N2	119.57 (17)	C10—C11—C12	111.70 (16)
C3—C4—N2	119.49 (17)	C10—C11—H112	108.7
C4—C3—C2	119.60 (16)	C12—C11—H112	110.4
C4—C3—H31	119.5	C10—C11—H111	109.4
C2—C3—H31	120.9	C12—C11—H111	107.7
C6—C7—C8	110.18 (14)	H112—C11—H111	108.9
C6—C7—H71	110.2	O3—C15—C16	110.69 (19)
C8—C7—H71	108.6	O3—C15—H152	104.8
C6—C7—H72	110.0	C16—C15—H152	110.0
C8—C7—H72	110.7	O3—C15—H151	108.1
H71—C7—H72	107.2	C16—C15—H151	111.3
C9—C8—C7	109.74 (14)	H152—C15—H151	111.7
C9—C8—C17	108.75 (14)	C15—C16—H162	109.3
C7—C8—C17	109.52 (15)	C15—C16—H161	110.0
C9—C8—C14	109.75 (14)	H162—C16—H161	109.0
C7—C8—C14	111.10 (14)	C15—C16—H163	110.6
C17—C8—C14	107.93 (15)	H162—C16—H163	108.3
C9—C10—C11	109.16 (14)	H161—C16—H163	109.6
C9—C10—H101	108.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H72···N3ⁱ	0.97	2.56	3.492 (3)	161

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉N₃O₄
M_r	329.36
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	8.8257 (4), 9.2256 (5), 10.5011 (6)
α, β, γ (°)	88.246 (4), 75.089 (2), 83.289 (3)
V (Å³)	820.57 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10064, 4189, 2794
R_int	0.04
(sin θ/λ)_max (Å⁻¹)	0.683

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.096, 1.04
No. of reflections	2503
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.26

Computer programs: COLLECT (Nonius, 2001), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SIR2004 (Burla et al., 2005), CRYSTALS (Betteridge et al., 2003), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H72···N3ⁱ	0.97	2.56	3.492 (3)	161

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors wish to thank the Laboratoire de Physique des Interactions Ioniques et Moléculaires of Provence University (France) for the use of the diffractometer.

References

Allen, F. H., Kennard, O., Wastson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Google Scholar
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Web of Science CrossRef IUCr Journals Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Crooke, S. T. & Bradner, W. T. (1976). Cancer Treat. Rev. 3, 121–139. CrossRef CAS PubMed Web of Science Google Scholar
Dalla Via, L., Gia, O., Gasparotto, V. & Ferlin, M. G. (2008). J. Med. Chem. 43, 429–434. CAS Google Scholar
Danishefsky, S. & Ciufolini, M. (1984). J. Am. Chem. Soc. 106, 6424–6425. CrossRef CAS Web of Science Google Scholar
Ferlin, M. G., Gatto, B., Chiarelotto, G. & Palumbo, M. (2000). Bioorg. Med. Chem. 8, 1415–1422. Web of Science CrossRef PubMed CAS Google Scholar
Gasparotto, V., Castalinolo, I., Chiarelotto, G., Pezzi, V., Montanaro, D., Brun, P., Palu, G., Viola, G. & Fer'lin, M. G. (2006). J. Med. Chem. 49, 1910–1915. Web of Science CrossRef PubMed CAS Google Scholar
Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Oliveira, C. D., Romeiro, G. A., Skakle, J. M. S., Wardell, J. L. & Wardell, S. M. S. V. (2006). Acta Cryst. E62, o1492–o1493. Web of Science CSD CrossRef IUCr Journals Google Scholar
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
Remers, W. A. (1980). In Anticancer Agents Based on Natural Product Models, edited by J. M. Cassady & J. D. Duoros, p. 131. New York: Academic Press. Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhuravleva, Y. A., Zimichev, A. V., Zemtsova, M. N., Rybakov, V. B. & Klimochkin, Y. N. (2009). Acta Cryst. E65, o2059. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 66| Part 7| July 2010| Page o1735

doi:10.1107/S160053681002283X

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

Ethyl 5-cyano-8-nitro-2,3,4,4a,5,6-hexa­hydro-1H-pyrido[1,2-a]quinoline-5-carboxylate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 5-cyano-8-nitro-2,3,4,4a,5,6-hexahydro-1H-pyrido[1,2-a]quinoline-5-carboxylate