Ethyl 3-(2-chloro-5,8-dimeth-oxy-quinolin-3-yl)-2-cyano-oxirane-2-carboxyl-ate.

The title mol-ecule, C(17)H(15)ClN(2)O(5), contains a quinolyl unit linked to a functionalized oxirane system with a 2,3-trans arrangement of the substituents (ester group versus quinol-yl). The structure can be described as being built up from zigzag layers parallel to (1[Formula: see text]0). The heterocyclic ring of the quinolyl unit forms a dihedral angle of 60.05 (1)° with the oxirane plane. The crystal packing is stabilized by inter-molecular C-H⋯O and C-H⋯N hydrogen bonding, resulting in the formation of an infinite three-dimensional network and reinforcing the cohesion between the layers.

Related literature

For applications of quinoline derivatives, see: Kansagra et al. (2000 ▶); Vasquez et al. (2004 ▶); Guo et al. (2009 ▶) Cunico et al. (2006 ▶); Mahamoud et al. (2006 ▶); Kumar et al. (2008 ▶); Hong et al. (2010 ▶). For the biological activity of naturally occurring oxiranes, see: Bino (1980 ▶); Cross (1960 ▶); Marco-Contelles et al. (2004 ▶); Pearson & Ong (1981 ▶). For applications of oxiranes, see: Hanson (1991 ▶); Kumar & Leelavathi (2007 ▶); Das et al. (2007 ▶); Boukhris et al. (1996 ▶); Ammadi et al., (1999 ▶). For our previous work on the preparation of quinoline derivatives, see: Bouraiou et al. (2008 ▶); Benzerka et al. (2008 ▶); Ladraa et al. (2010 ▶). For weak hydrogen bonds, see: Desiraju & Steiner, (1999 ▶).

Experimental

Crystal data

C17H15ClN2O5

M = 362.76

Triclinic,

a = 8.3784 (3) Å

b = 10.1071 (4) Å

c = 10.7027 (4) Å

α = 102.489 (2)°

β = 103.977 (2)°

γ = 96.026 (2)°

V = 846.77 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 150 K

0.28 × 0.21 × 0.12 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.842, T max = 0.970

12867 measured reflections

3803 independent reflections

3369 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.141

S = 1.02

3803 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023336/zj2015sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023336/zj2015Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023336/zj2015Isup3.cml

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

C17H15ClN2O5	Z = 2
Mr = 362.76	F(000) = 376
Triclinic, P1	Dx = 1.423 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3784 (3) Å	Cell parameters from 7904 reflections
b = 10.1071 (4) Å	θ = 2.5–27.5°
c = 10.7027 (4) Å	µ = 0.26 mm−1
α = 102.489 (2)°	T = 150 K
β = 103.977 (2)°	Block, colourless
γ = 96.026 (2)°	0.28 × 0.21 × 0.12 mm
V = 846.77 (6) Å3

Bruker APEXII diffractometer	3369 reflections with I > 2σ(I)
graphite	Rint = 0.020
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −10→10
Tmin = 0.842, Tmax = 0.970	k = −13→13
12867 measured reflections	l = −13→10
3803 independent 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) = 0.141	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0775P)2 + 0.5515P] where P = (Fo2 + 2Fc2)/3
3803 reflections	(Δ/σ)max = 0.006
229 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

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
Cl1	0.21857 (5)	−0.03042 (5)	1.03331 (5)	0.03620 (16)
C1	0.3363 (2)	0.09251 (17)	0.98421 (17)	0.0277 (4)
N2	0.45074 (18)	0.18016 (15)	1.07892 (14)	0.0279 (3)
C3	0.5441 (2)	0.27800 (17)	1.04347 (17)	0.0274 (4)
C4	0.6751 (2)	0.37174 (18)	1.14484 (18)	0.0312 (4)
O5	0.69369 (17)	0.35382 (14)	1.27008 (13)	0.0379 (3)
C6	0.8178 (3)	0.4523 (3)	1.3736 (2)	0.0508 (6)
H6A	0.9272	0.448	1.3567	0.076*
H6B	0.8202	0.4318	1.4593	0.076*
H6C	0.7909	0.5447	1.3756	0.076*
C7	0.7706 (2)	0.4691 (2)	1.1101 (2)	0.0371 (4)
H7	0.8587	0.5309	1.177	0.045*
C8	0.7410 (3)	0.4798 (2)	0.9768 (2)	0.0387 (4)
H8	0.8091	0.5483	0.9558	0.046*
C9	0.6153 (2)	0.3923 (2)	0.8783 (2)	0.0349 (4)
O10	0.5731 (2)	0.39496 (16)	0.74704 (15)	0.0439 (4)
C11	0.6705 (3)	0.4986 (2)	0.7119 (2)	0.0502 (6)
H11A	0.6632	0.5894	0.7635	0.075*
H11B	0.628	0.4926	0.6168	0.075*
H11C	0.7871	0.4848	0.7313	0.075*
C12	0.5154 (2)	0.28768 (18)	0.90951 (18)	0.0307 (4)
C13	0.3894 (2)	0.18913 (19)	0.81199 (18)	0.0326 (4)
H13	0.3669	0.1923	0.7214	0.039*
C14	0.2996 (2)	0.08919 (18)	0.84700 (17)	0.0309 (4)
C15	0.1747 (3)	−0.0235 (2)	0.74667 (18)	0.0367 (4)
H15	0.1828	−0.1184	0.7581	0.044*
O16	0.13334 (18)	−0.01119 (16)	0.61244 (13)	0.0421 (4)
C17	0.0041 (2)	−0.00089 (19)	0.67835 (18)	0.0347 (4)
C18	−0.0392 (2)	0.1364 (2)	0.7104 (2)	0.0379 (4)
N19	−0.0698 (2)	0.2443 (2)	0.7373 (3)	0.0590 (6)
C20	−0.1344 (3)	−0.1243 (2)	0.6298 (2)	0.0429 (5)
O21	−0.1073 (3)	−0.23961 (17)	0.6035 (2)	0.0796 (7)
O22	−0.27917 (19)	−0.08591 (15)	0.62274 (14)	0.0423 (4)
C23	−0.4215 (3)	−0.1992 (3)	0.5871 (3)	0.0537 (6)
H23A	−0.4089	−0.275	0.516	0.064*
H23B	−0.4248	−0.2353	0.6655	0.064*
C24	−0.5687 (4)	−0.1501 (3)	0.5431 (4)	0.0786 (10)
H24A	−0.5758	−0.07	0.6108	0.118*
H24B	−0.6643	−0.2222	0.5272	0.118*
H24C	−0.5697	−0.1233	0.4602	0.118*

	U11	U22	U33	U12	U13	U23
Cl1	0.0300 (2)	0.0350 (3)	0.0367 (3)	−0.00048 (17)	0.00372 (17)	0.00336 (18)
C1	0.0245 (8)	0.0253 (8)	0.0276 (8)	0.0055 (6)	0.0001 (6)	0.0016 (6)
N2	0.0247 (7)	0.0284 (7)	0.0248 (7)	0.0059 (6)	−0.0002 (5)	0.0013 (6)
C3	0.0245 (8)	0.0254 (8)	0.0274 (8)	0.0075 (6)	0.0008 (6)	0.0018 (6)
C4	0.0277 (8)	0.0294 (9)	0.0292 (9)	0.0059 (7)	−0.0003 (7)	0.0009 (7)
O5	0.0337 (7)	0.0392 (7)	0.0265 (7)	−0.0048 (6)	−0.0059 (5)	−0.0005 (5)
C6	0.0442 (12)	0.0547 (13)	0.0318 (11)	−0.0119 (10)	−0.0056 (8)	−0.0069 (9)
C7	0.0311 (9)	0.0294 (9)	0.0416 (11)	0.0026 (7)	0.0007 (8)	0.0012 (8)
C8	0.0392 (10)	0.0312 (9)	0.0458 (11)	0.0059 (8)	0.0114 (9)	0.0098 (8)
C9	0.0392 (10)	0.0316 (9)	0.0350 (10)	0.0110 (8)	0.0096 (8)	0.0087 (8)
O10	0.0538 (9)	0.0443 (8)	0.0356 (8)	0.0093 (7)	0.0116 (6)	0.0144 (6)
C11	0.0678 (15)	0.0415 (12)	0.0497 (13)	0.0123 (11)	0.0237 (11)	0.0188 (10)
C12	0.0309 (9)	0.0293 (9)	0.0290 (9)	0.0109 (7)	0.0032 (7)	0.0040 (7)
C13	0.0379 (10)	0.0318 (9)	0.0235 (8)	0.0124 (7)	0.0005 (7)	0.0033 (7)
C14	0.0308 (9)	0.0287 (8)	0.0252 (8)	0.0093 (7)	−0.0029 (7)	−0.0004 (7)
C15	0.0411 (10)	0.0302 (9)	0.0272 (9)	0.0067 (8)	−0.0045 (7)	−0.0016 (7)
O16	0.0419 (8)	0.0488 (8)	0.0239 (7)	0.0100 (6)	−0.0022 (5)	−0.0037 (6)
C17	0.0367 (10)	0.0301 (9)	0.0269 (9)	0.0031 (7)	−0.0036 (7)	0.0003 (7)
C18	0.0265 (9)	0.0329 (10)	0.0426 (11)	−0.0005 (7)	−0.0027 (7)	0.0008 (8)
N19	0.0366 (10)	0.0347 (10)	0.0865 (16)	0.0036 (8)	−0.0016 (10)	−0.0033 (10)
C20	0.0435 (11)	0.0354 (10)	0.0332 (10)	−0.0011 (8)	−0.0092 (8)	−0.0004 (8)
O21	0.0689 (12)	0.0308 (9)	0.1015 (17)	0.0017 (8)	−0.0163 (11)	−0.0143 (9)
O22	0.0436 (8)	0.0386 (8)	0.0362 (7)	−0.0092 (6)	0.0032 (6)	0.0081 (6)
C23	0.0507 (13)	0.0498 (13)	0.0491 (13)	−0.0164 (10)	0.0050 (10)	0.0094 (10)
C24	0.0601 (17)	0.0529 (16)	0.126 (3)	0.0022 (13)	0.0284 (18)	0.0286 (18)

Cl1—C1	1.7514 (19)	C11—H11C	0.98
C1—N2	1.302 (2)	C12—C13	1.412 (3)
C1—C14	1.418 (2)	C13—C14	1.366 (3)
N2—C3	1.370 (2)	C13—H13	0.95
C3—C12	1.422 (2)	C14—C15	1.492 (2)
C3—C4	1.429 (2)	C15—O16	1.430 (2)
C4—O5	1.365 (2)	C15—C17	1.505 (3)
C4—C7	1.372 (3)	C15—H15	1
O5—C6	1.431 (2)	O16—C17	1.429 (3)
C6—H6A	0.98	C17—C18	1.461 (3)
C6—H6B	0.98	C17—C20	1.516 (3)
C6—H6C	0.98	C18—N19	1.139 (3)
C7—C8	1.417 (3)	C20—O21	1.197 (3)
C7—H7	0.95	C20—O22	1.302 (3)
C8—C9	1.367 (3)	O22—C23	1.478 (3)
C8—H8	0.95	C23—C24	1.393 (4)
C9—O10	1.371 (2)	C23—H23A	0.99
C9—C12	1.425 (3)	C23—H23B	0.99
O10—C11	1.430 (3)	C24—H24A	0.98
C11—H11A	0.98	C24—H24B	0.98
C11—H11B	0.98	C24—H24C	0.98
N2—C1—C14	125.66 (17)	C14—C13—C12	120.43 (17)
N2—C1—Cl1	116.16 (14)	C14—C13—H13	119.8
C14—C1—Cl1	118.18 (13)	C12—C13—H13	119.8
C1—N2—C3	117.43 (15)	C13—C14—C1	116.95 (16)
N2—C3—C12	122.01 (15)	C13—C14—C15	122.41 (17)
N2—C3—C4	118.49 (16)	C1—C14—C15	120.56 (17)
C12—C3—C4	119.50 (17)	O16—C15—C14	116.67 (17)
O5—C4—C7	125.88 (16)	O16—C15—C17	58.19 (12)
O5—C4—C3	115.19 (16)	C14—C15—C17	122.08 (16)
C7—C4—C3	118.92 (17)	O16—C15—H15	115.8
C4—O5—C6	115.66 (16)	C14—C15—H15	115.8
O5—C6—H6A	109.5	C17—C15—H15	115.8
O5—C6—H6B	109.5	C17—O16—C15	63.54 (12)
H6A—C6—H6B	109.5	O16—C17—C18	114.72 (17)
O5—C6—H6C	109.5	O16—C17—C15	58.27 (12)
H6A—C6—H6C	109.5	C18—C17—C15	118.78 (16)
H6B—C6—H6C	109.5	O16—C17—C20	114.39 (16)
C4—C7—C8	121.65 (18)	C18—C17—C20	118.84 (17)
C4—C7—H7	119.2	C15—C17—C20	117.05 (17)
C8—C7—H7	119.2	N19—C18—C17	178.6 (2)
C9—C8—C7	120.54 (19)	O21—C20—O22	127.0 (2)
C9—C8—H8	119.7	O21—C20—C17	122.2 (2)
C7—C8—H8	119.7	O22—C20—C17	110.79 (17)
C8—C9—O10	125.59 (18)	C20—O22—C23	115.01 (18)
C8—C9—C12	119.68 (18)	C24—C23—O22	109.0 (2)
O10—C9—C12	114.73 (17)	C24—C23—H23A	109.9
C9—O10—C11	116.36 (18)	O22—C23—H23A	109.9
O10—C11—H11A	109.5	C24—C23—H23B	109.9
O10—C11—H11B	109.5	O22—C23—H23B	109.9
H11A—C11—H11B	109.5	H23A—C23—H23B	108.3
O10—C11—H11C	109.5	C23—C24—H24A	109.5
H11A—C11—H11C	109.5	C23—C24—H24B	109.5
H11B—C11—H11C	109.5	H24A—C24—H24B	109.5
C13—C12—C3	117.46 (17)	C23—C24—H24C	109.5
C13—C12—C9	122.83 (17)	H24A—C24—H24C	109.5
C3—C12—C9	119.69 (17)	H24B—C24—H24C	109.5
C14—C1—N2—C3	0.1 (3)	C12—C13—C14—C1	1.7 (3)
Cl1—C1—N2—C3	−179.64 (12)	C12—C13—C14—C15	−175.11 (16)
C1—N2—C3—C12	1.9 (2)	N2—C1—C14—C13	−1.9 (3)
C1—N2—C3—C4	−177.41 (15)	Cl1—C1—C14—C13	177.79 (13)
N2—C3—C4—O5	−0.2 (2)	N2—C1—C14—C15	174.96 (17)
C12—C3—C4—O5	−179.61 (15)	Cl1—C1—C14—C15	−5.3 (2)
N2—C3—C4—C7	179.25 (16)	C13—C14—C15—O16	−9.4 (3)
C12—C3—C4—C7	−0.1 (3)	C1—C14—C15—O16	173.87 (16)
C7—C4—O5—C6	4.2 (3)	C13—C14—C15—C17	−77.0 (3)
C3—C4—O5—C6	−176.33 (17)	C1—C14—C15—C17	106.3 (2)
O5—C4—C7—C8	−179.77 (17)	C14—C15—O16—C17	−112.82 (19)
C3—C4—C7—C8	0.8 (3)	C15—O16—C17—C18	109.79 (18)
C4—C7—C8—C9	−0.1 (3)	C15—O16—C17—C20	−107.86 (18)
C7—C8—C9—O10	178.50 (18)	C14—C15—C17—O16	103.6 (2)
C7—C8—C9—C12	−1.3 (3)	O16—C15—C17—C18	−102.8 (2)
C8—C9—O10—C11	0.2 (3)	C14—C15—C17—C18	0.8 (3)
C12—C9—O10—C11	179.96 (17)	O16—C15—C17—C20	103.26 (19)
N2—C3—C12—C13	−2.0 (2)	C14—C15—C17—C20	−153.18 (19)
C4—C3—C12—C13	177.30 (15)	O16—C17—C20—O21	40.3 (3)
N2—C3—C12—C9	179.44 (15)	C18—C17—C20—O21	−179.0 (2)
C4—C3—C12—C9	−1.2 (3)	C15—C17—C20—O21	−25.1 (3)
C8—C9—C12—C13	−176.53 (17)	O16—C17—C20—O22	−140.08 (17)
O10—C9—C12—C13	3.7 (3)	C18—C17—C20—O22	0.6 (3)
C8—C9—C12—C3	1.9 (3)	C15—C17—C20—O22	154.55 (18)
O10—C9—C12—C3	−177.88 (15)	O21—C20—O22—C23	4.5 (4)
C3—C12—C13—C14	0.1 (3)	C17—C20—O22—C23	−175.12 (17)
C9—C12—C13—C14	178.57 (16)	C20—O22—C23—C24	−161.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N19i	0.95	2.57	3.434 (3)	151
C24—H24A···O16ii	0.98	2.57	3.152 (4)	118
C13—H13···O16	0.95	2.54	2.875 (2)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯N19i	0.95	2.57	3.434 (3)	151
C24—H24A⋯O16ii	0.98	2.57	3.152 (4)	118

Symmetry codes: (i) ; (ii) .