3-(1,3-Dioxolan-2-yl)-6,7-dimethoxy­quinoline

In the mol­ecule of the title compound, C₁₄H₁₅NO₄, the quinoline ring system and meth­oxy substituents are located on a crystallographic mirror plane. The 1,3-dioxolane ring adopts an envelope conformation.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.131
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.70 mm
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.65 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Quinolines are an important group of heterocyclic compounds. Among these, 2-chloro-3-formylquinolines occupy a prominent position as they are key intermediates for further (β)-annelation of a wide variety of rings and for various functional group interconversions (Meth-Cohn, 1993).

Literature survey revealed that substituted quinolines possess diverse chemotherapeutic activities including antibacterial, (Kayirere et al., 1998, Kidwai et al., 2000) antifungal, (Musiol et al., 2006) antiamoebic, (Burkhaller et al., 1951; Bailey et al., 1979) antileishmanial, (Dade et al., 2001; Jain et al., 2005) antimalarial, (Charris et al., 2005; Cunico et al., 2006) and antitumor activities. (Zhao et al., 2005; Chen et al., 2006).

The title compound, (I) consists of a -6,7-dimethoxyquinoline unit linked to a (1,3-dioxolan-2-yl)ring (Fig. 1). The geometric parameters of (I) are in agreement with those of other structures possessing a quinolyl substituent and dioxolane previously reported in the literature (Bouraiou et al., 2007a,b; Garden et al., 2007).

The 1,3-dioxolane ring adopts a twisted conformation. The crystal structure can be described by intercalled layers stacked along the b axis in 1/4, 3/4. No classical hydrogen bonds were found in the crystal structure.

Related literature

For general background, see: Kayirere et al. (1998); Kidwai et al. (2000); Zhao et al. (2005); Charris et al. (2005); Cunico et al. (2006); Musiol et al. (2006); Chen et al. (2006). For synthesis see: Meth-Cohn et al. (1981); Meth-Cohn (1993). For related structures, see: Bouraiou et al. (2007a,b).

For related literature, see: Bailey et al. (1979); Burkhaller & Edgerton (1951); Dade et al. (2001); Garden et al. (2007); Jain et al. (2005).

S2. Experimental

The title compound was synthesized by refluxing 2-chloro-3-formyl-6,7-dimethoxyquinoline(3.6 mmol) according to the literature procedure of Meth-Cohn et al. (1981) with ethelyne glycol(7.1 mmol)in toluene(35 ml) for 3 h. The contents were then evoporated dryness and added the solution of NiCl₂, 6 H₂O(3.6 mmol),triphenylphosphine(14.4 mmol) and zinc powder(3.8 mmol) in DMF(20 ml) was stirring at 70° C for 2 h. A White solid was obtained that was purifed by chromatography ehtylacetate-pentane (3:2) Crystals suitable for X-ray analysis were obtained by slow evaporation of a toluene solution of (I).

S3. Refinement

All H atoms were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic), O.96 Å (methyl), 0.97 Å (methylene) and 0.98 Å (methine) with U_iso(H) = 1.2U_eq(C) or U_iso(H) = 1.5U_eq(methyl).

Computing details

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia,1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. The molecular structure of (I), with atom labelling scheme. Ellipsoids are drawn at the 50% probability level·H atoms are represented as small spheres of arbitrary radii. [Symmetry codes: (i) x, 1/2 - y, z].
	Fig. 2. Partial packing view showing the intercalled layers. H atoms have been omitted for clarity.

3-(1,3-Dioxolan-2-yl)-6,7-dimethoxyquinoline

Crystal data

C14H15NO4	F(000) = 552
Mr = 261.27	Dx = 1.417 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 5615 reflections
a = 13.847 (2) Å	θ = 2.2–27.4°
b = 7.0960 (12) Å	µ = 0.10 mm^−1
c = 12.467 (2) Å	T = 100 K
V = 1225.0 (3) Å^3	Prism, colourless
Z = 4	0.7 × 0.65 × 0.6 mm

Data collection

Bruker APEXII diffractometer	1378 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	h = 0→17
Tmin = 0.921, Tmax = 0.939	k = 0→9
12283 measured reflections	l = 0→16
1504 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0676P)^2 + 0.8241P] where P = (Fo^2 + 2Fc^2)/3
1508 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.25658 (12)	0.2500	0.28355 (13)	0.0178 (4)
O1	0.39995 (7)	0.08969 (14)	0.56778 (7)	0.0197 (3)
O2	0.48367 (10)	0.2500	−0.08196 (11)	0.0216 (3)
O3	0.30037 (10)	0.2500	−0.09922 (11)	0.0208 (3)
C2	0.31740 (13)	0.2500	0.19680 (14)	0.0149 (4)
C3	0.27537 (13)	0.2500	0.09301 (15)	0.0156 (4)
H3	0.2085	0.2500	0.0857	0.019*
C4	0.33269 (14)	0.2500	0.00341 (14)	0.0157 (4)
C5	0.43621 (13)	0.2500	0.01377 (15)	0.0157 (4)
C6	0.47828 (13)	0.2500	0.11308 (15)	0.0158 (4)
H6	0.5452	0.2500	0.1193	0.019*
C7	0.41971 (13)	0.2500	0.20700 (15)	0.0147 (4)
C8	0.45894 (13)	0.2500	0.31164 (15)	0.0153 (4)
H8	0.5255	0.2500	0.3216	0.018*
C9	0.39822 (13)	0.2500	0.39823 (15)	0.0158 (4)
C10	0.29715 (14)	0.2500	0.37939 (15)	0.0177 (4)
H10	0.2566	0.2500	0.4388	0.021*
C11	0.43506 (14)	0.2500	0.51138 (14)	0.0163 (4)
H11	0.5058	0.2500	0.5115	0.020*
C12	0.38835 (16)	0.1471 (2)	0.67633 (12)	0.0391 (5)
H12A	0.4410	0.0995	0.7199	0.047*
H12B	0.3280	0.0995	0.7050	0.047*
C13	0.58676 (14)	0.2500	−0.07773 (17)	0.0233 (5)
H13A	0.6123	0.2500	−0.1493	0.035*
H13B	0.6086	0.1395	−0.0405	0.035*	0.50
H13C	0.6086	0.3605	−0.0405	0.035*	0.50
C14	0.19740 (14)	0.2500	−0.11326 (15)	0.0226 (4)
H14A	0.1824	0.2500	−0.1884	0.034*
H14B	0.1705	0.3605	−0.0804	0.034*	0.50
H14C	0.1705	0.1395	−0.0804	0.034*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0164 (8)	0.0218 (8)	0.0152 (8)	0.000	0.0019 (6)	0.000
O1	0.0308 (6)	0.0158 (5)	0.0125 (5)	−0.0005 (4)	0.0011 (3)	0.0000 (4)
O2	0.0157 (7)	0.0348 (8)	0.0142 (7)	0.000	0.0021 (5)	0.000
O3	0.0154 (7)	0.0350 (8)	0.0118 (6)	0.000	−0.0013 (5)	0.000
C2	0.0164 (9)	0.0142 (8)	0.0142 (8)	0.000	0.0008 (6)	0.000
C3	0.0139 (8)	0.0173 (9)	0.0157 (9)	0.000	0.0000 (7)	0.000
C4	0.0173 (9)	0.0163 (9)	0.0136 (8)	0.000	−0.0026 (7)	0.000
C5	0.0150 (9)	0.0174 (9)	0.0147 (9)	0.000	0.0017 (7)	0.000
C6	0.0132 (8)	0.0178 (9)	0.0165 (9)	0.000	0.0001 (6)	0.000
C7	0.0160 (9)	0.0130 (8)	0.0151 (8)	0.000	−0.0004 (7)	0.000
C8	0.0149 (8)	0.0142 (8)	0.0168 (9)	0.000	−0.0010 (7)	0.000
C9	0.0185 (9)	0.0155 (9)	0.0134 (8)	0.000	−0.0012 (7)	0.000
C10	0.0175 (9)	0.0221 (9)	0.0135 (8)	0.000	0.0030 (7)	0.000
C11	0.0182 (9)	0.0177 (9)	0.0130 (8)	0.000	−0.0007 (7)	0.000
C12	0.0831 (14)	0.0203 (9)	0.0137 (7)	−0.0020 (8)	0.0098 (7)	−0.0011 (6)
C13	0.0159 (9)	0.0344 (12)	0.0196 (9)	0.000	0.0049 (7)	0.000
C14	0.0158 (9)	0.0361 (12)	0.0158 (9)	0.000	−0.0029 (7)	0.000

Geometric parameters (Å, º)

N1—C10	1.320 (2)	C8—C9	1.368 (3)
N1—C2	1.371 (2)	C8—H8	0.9300
O1—C12	1.4225 (17)	C9—C10	1.419 (3)
O1—C11	1.4229 (15)	C9—C11	1.500 (2)
O2—C5	1.362 (2)	C10—H10	0.9300
O2—C13	1.428 (2)	C11—O1^i	1.4229 (15)
O3—C4	1.356 (2)	C11—H11	0.9800
O3—C14	1.437 (2)	C12—C12^i	1.460 (3)
C2—C3	1.419 (2)	C12—H12A	0.9700
C2—C7	1.422 (3)	C12—H12B	0.9700
C3—C4	1.370 (3)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.439 (3)	C13—H13C	0.9600
C5—C6	1.368 (3)	C14—H14A	0.9600
C6—C7	1.424 (2)	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—C8	1.413 (2)
C10—N1—C2	116.91 (16)	N1—C10—C9	124.70 (17)
C12—O1—C11	106.24 (11)	N1—C10—H10	117.6
C5—O2—C13	116.73 (15)	C9—C10—H10	117.6
C4—O3—C14	116.27 (14)	O1—C11—O1^i	106.15 (14)
N1—C2—C3	117.88 (16)	O1—C11—C9	110.40 (10)
N1—C2—C7	122.77 (17)	O1^i—C11—C9	110.40 (10)
C3—C2—C7	119.35 (16)	O1—C11—H11	109.9
C4—C3—C2	120.39 (17)	O1^i—C11—H11	109.9
C4—C3—H3	119.8	C9—C11—H11	109.9
C2—C3—H3	119.8	O1—C12—C12^i	106.65 (8)
O3—C4—C3	125.33 (17)	O1—C12—H12A	110.4
O3—C4—C5	114.42 (16)	C12^i—C12—H12A	110.4
C3—C4—C5	120.25 (16)	O1—C12—H12B	110.4
O2—C5—C6	125.96 (17)	C12^i—C12—H12B	110.4
O2—C5—C4	113.69 (16)	H12A—C12—H12B	108.6
C6—C5—C4	120.35 (16)	O2—C13—H13A	109.5
C5—C6—C7	120.09 (17)	O2—C13—H13B	109.5
C5—C6—H6	120.0	H13A—C13—H13B	109.5
C7—C6—H6	120.0	O2—C13—H13C	109.5
C8—C7—C2	117.74 (17)	H13A—C13—H13C	109.5
C8—C7—C6	122.69 (17)	H13B—C13—H13C	109.5
C2—C7—C6	119.57 (16)	O3—C14—H14A	109.5
C9—C8—C7	119.48 (17)	O3—C14—H14B	109.5
C9—C8—H8	120.3	H14A—C14—H14B	109.5
C7—C8—H8	120.3	O3—C14—H14C	109.5
C8—C9—C10	118.39 (17)	H14A—C14—H14C	109.5
C8—C9—C11	122.21 (16)	H14B—C14—H14C	109.5
C10—C9—C11	119.41 (16)
C12—O1—C11—O1^i	−27.90 (19)	C8—C9—C11—O1	−121.47 (10)
C12—O1—C11—C9	−147.55 (14)	C10—C9—C11—O1	58.53 (10)
C8—C9—C11—O1^i	121.47 (10)	C11—O1—C12—C12^i	17.06 (11)
C10—C9—C11—O1^i	−58.53 (10)

Symmetry code: (i) x, −y+1/2, z.