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Acta Cryst. (2007). E63, o3439
https://doi.org/10.1107/S160053680703214X
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5-[(8-Hydroxy­quinolin-2-yl­amino)­methyl­ene]-2,2-dimethyl-1,3-dioxane-4,6-dione

L. E. da Silva, P. T. de Sousa Jr, E. L. Dall'Oglio and S. Foro
In the title compound, C16H14N2O5, the 1,3-dioxane-4,6-dione ring is in an envelope conformation. The C—N—C—C torsion angle between the nearly planar quinoline ring system carrying the OH group and the 1,3-dioxane-4,6-dione unit is −177.1 (1)°. The NH group has an intra­molecular contact to a carbonyl O atom, forming a six-membered ring, and also an inter­molecular contact to the carbonyl O atom. One intra­molecular O—H...N and two inter­molecular C—H...O hydrogen bonds are also observed. Two mol­ecules are connected by these hydrogen bonds, forming layers.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703214X/nc2044sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680703214X/nc2044Isup2.hkl
Contains datablock I

CCDC reference: 657719

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Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.046
  • wR factor = 0.119
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found




Alert level C
ABSTY03_ALERT_1_C  The _exptl_absorpt_correction_type has been given as none.
            However values have been given for Tmin and Tmax. Remove
            these if an absorption correction has not been applied.
  From the CIF: _exptl_absorpt_correction_T_min   0.622
  From the CIF: _exptl_absorpt_correction_T_max   0.761
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT430_ALERT_2_C Short Inter D...A Contact  O4     ..  O4      ..       2.86 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      49.00 A   3 


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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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



checkCIF publication errors


Alert level A
PUBL002_ALERT_1_A  The contact author's address is missing,
            _publ_contact_author_address.


   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing
Comment top

Aminoquinolines are important constituents in a variety of pharmaceutically important compound classes, most notably perhaps the antimalarials quinine, chloroquine, and their derivatives (Storz, 2004). On the other hands, Meldrum's acid and its derivatives serve as key intermediates for the synthesis of heterocyclic compounds with pharmacological activity (Gaber & McNab, 2001). In order to investigate the structure-function relationships and develop more effective antiparasitic drugs based on nitrogen heterocyclic derivatives (da Silva et al., 2007; da Silva et al., 2002), we report here the crystal structure of the title compound (I).

In (I), the 1,3-dioxane-4,6-dione ring is an envelope conformation with C13 in the flap position. The quinoline ring system, with the OH group, is nearly planar with maximum deviations from the mean plane of -0.0127 (9) Å for atom N1 and 0.0097 (9) Å for atom O3. The dihedral angle C11—C10—N2—C1 is -177.1 (1)° and the distances C1—N2 and C10—C11 indicate delocalization of the conjugated system. The amino H atom forms an intra- and an intermolecular contact to the carbonyl O4 atom. One intramolecular O—H···N and two intermolecular C—H···O hydrogen bonds were also observed. The packing diagram illustrates that two hydrogen-bonded molecules are related by an inversion centre building layers (Fig. 2). Details of the hydrogen-bonding parameters are given in Table 1.

Related literature top

For related literature, see: Cassis et al. (1985); Gaber & McNab (2001); da Silva et al. (2002, 2007); Storz (2004).

Experimental top

The title compound was prepared according to a literature procedure (Cassis et al., 1985). Single crystals of (I) suitable for X-ray data collection were obtained by slow evaporation from a solution of methanol:DCM (1:1). m.p.: 501–502 K.

Refinement top

The methyl H atoms were positioned with idealized geometry using a riding model with C—H = 0.96 Å. The other H atoms were located in difference map, and their positional parameters were refined freely [N—H = 0.85 (2) Å, O—H = 0.78 (2) Å and C—H = 0.87 (2)–1.00 (2) Å]. Uiso(H) values were set to 1.2Ueq (1.5Ueq for methyl) of the parent atom.

Structure description top

Aminoquinolines are important constituents in a variety of pharmaceutically important compound classes, most notably perhaps the antimalarials quinine, chloroquine, and their derivatives (Storz, 2004). On the other hands, Meldrum's acid and its derivatives serve as key intermediates for the synthesis of heterocyclic compounds with pharmacological activity (Gaber & McNab, 2001). In order to investigate the structure-function relationships and develop more effective antiparasitic drugs based on nitrogen heterocyclic derivatives (da Silva et al., 2007; da Silva et al., 2002), we report here the crystal structure of the title compound (I).

In (I), the 1,3-dioxane-4,6-dione ring is an envelope conformation with C13 in the flap position. The quinoline ring system, with the OH group, is nearly planar with maximum deviations from the mean plane of -0.0127 (9) Å for atom N1 and 0.0097 (9) Å for atom O3. The dihedral angle C11—C10—N2—C1 is -177.1 (1)° and the distances C1—N2 and C10—C11 indicate delocalization of the conjugated system. The amino H atom forms an intra- and an intermolecular contact to the carbonyl O4 atom. One intramolecular O—H···N and two intermolecular C—H···O hydrogen bonds were also observed. The packing diagram illustrates that two hydrogen-bonded molecules are related by an inversion centre building layers (Fig. 2). Details of the hydrogen-bonding parameters are given in Table 1.

For related literature, see: Cassis et al. (1985); Gaber & McNab (2001); da Silva et al. (2002, 2007); Storz (2004).

Computing details top

Data collection: CAD-4-PC Software (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom labeling and displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.
5-[(8-Hydroxyquinolin-2-ylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione top
Crystal data top
C16H14N2O5Z = 2
Mr = 314.29F(000) = 328
Triclinic, P1Dx = 1.379 Mg m−3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54180 Å
a = 7.445 (2) ÅCell parameters from 25 reflections
b = 8.440 (2) Åθ = 5.6–25.2°
c = 12.906 (3) ŵ = 0.88 mm−1
α = 77.31 (1)°T = 299 K
β = 86.81 (2)°Prism, colourless
γ = 73.15 (1)°0.60 × 0.40 × 0.33 mm
V = 757.2 (3) Å3
Data collection top
Enraf–Nonius CAD4
diffractometer		Rint = 0.053
Radiation source: fine-focus sealed tubeθmax = 66.9°, θmin = 3.5°
Graphite monochromatorh = −8→8
ω/2θ scansk = −10→10
5325 measured reflectionsl = −15→15
2704 independent reflections3 standard reflections every 120 min
2436 reflections with I > 2σ(I) intensity decay: 1.0%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.120 w = 1/[σ2(Fo2) + (0.0542P)2 + 0.1625P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.002
2704 reflectionsΔρmax = 0.27 e Å−3
233 parametersΔρmin = −0.18 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0292 (18)
Crystal data top
C16H14N2O5γ = 73.15 (1)°
Mr = 314.29V = 757.2 (3) Å3
Triclinic, P1Z = 2
a = 7.445 (2) ÅCu Kα radiation
b = 8.440 (2) ŵ = 0.88 mm−1
c = 12.906 (3) ÅT = 299 K
α = 77.31 (1)°0.60 × 0.40 × 0.33 mm
β = 86.81 (2)°
Data collection top
Enraf–Nonius CAD4
diffractometer		Rint = 0.053
5325 measured reflections3 standard reflections every 120 min
2704 independent reflections intensity decay: 1.0%
2436 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.27 e Å−3
2704 reflectionsΔρmin = −0.18 e Å−3
233 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
xyzUiso*/Ueq
C10.87562 (18)0.18229 (16)1.03493 (11)0.0356 (3)
C20.8419 (2)0.11498 (19)1.14199 (12)0.0433 (4)
H20.742 (3)0.061 (2)1.1559 (13)0.052*
C30.9522 (2)0.1279 (2)1.21805 (12)0.0465 (4)
H30.936 (3)0.084 (2)1.2920 (15)0.056*
C41.0967 (2)0.20732 (18)1.18985 (11)0.0415 (3)
C51.2181 (3)0.2261 (2)1.26336 (14)0.0532 (4)
H51.203 (3)0.191 (2)1.3366 (16)0.064*
C61.3538 (2)0.3041 (2)1.22804 (15)0.0559 (4)
H61.442 (3)0.319 (2)1.2787 (16)0.067*
C71.3758 (2)0.3669 (2)1.11993 (14)0.0493 (4)
H71.471 (3)0.422 (2)1.0951 (14)0.059*
C81.26047 (19)0.34956 (17)1.04695 (12)0.0402 (3)
C91.11806 (18)0.26817 (16)1.08037 (11)0.0358 (3)
C100.7677 (2)0.23140 (17)0.85433 (11)0.0391 (3)
H100.855 (3)0.281 (2)0.8346 (13)0.047*
C110.65092 (19)0.22806 (17)0.77695 (11)0.0384 (3)
C120.50124 (19)0.14834 (17)0.80186 (10)0.0367 (3)
C130.3749 (2)0.2999 (2)0.62899 (11)0.0469 (4)
C140.6902 (2)0.2936 (2)0.66727 (12)0.0484 (4)
C150.2853 (3)0.2547 (3)0.54213 (13)0.0674 (5)
H15A0.28190.33780.47760.101*
H15B0.15980.25250.56200.101*
H15C0.35720.14520.53140.101*
C160.2690 (3)0.4675 (2)0.65367 (14)0.0610 (5)
H16A0.32880.48630.71200.091*
H16B0.14240.46730.67240.091*
H16C0.26790.55610.59240.091*
N11.00832 (15)0.25491 (13)1.00330 (9)0.0360 (3)
N20.75720 (16)0.16946 (14)0.95745 (9)0.0384 (3)
H2N0.677 (3)0.116 (2)0.9798 (13)0.046*
O10.38313 (15)0.16567 (14)0.72143 (8)0.0478 (3)
O20.56184 (16)0.30024 (16)0.59423 (8)0.0546 (3)
O31.27855 (16)0.41060 (14)0.94136 (9)0.0502 (3)
H3O1.205 (3)0.386 (3)0.9114 (16)0.060*
O40.47832 (15)0.06465 (13)0.88781 (8)0.0445 (3)
O50.82846 (18)0.3362 (2)0.63562 (10)0.0747 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0278 (6)0.0356 (7)0.0447 (7)−0.0111 (5)−0.0029 (5)−0.0076 (5)
C20.0353 (7)0.0496 (8)0.0488 (8)−0.0221 (6)−0.0007 (6)−0.0043 (6)
C30.0444 (8)0.0572 (9)0.0408 (8)−0.0239 (7)−0.0012 (6)−0.0036 (6)
C40.0354 (7)0.0445 (7)0.0471 (8)−0.0145 (6)−0.0034 (6)−0.0096 (6)
C50.0518 (9)0.0652 (10)0.0493 (9)−0.0250 (8)−0.0077 (7)−0.0131 (7)
C60.0468 (9)0.0632 (10)0.0678 (11)−0.0230 (8)−0.0127 (8)−0.0217 (8)
C70.0353 (8)0.0478 (8)0.0728 (11)−0.0201 (6)−0.0014 (7)−0.0182 (7)
C80.0305 (7)0.0364 (7)0.0559 (8)−0.0117 (5)0.0026 (6)−0.0120 (6)
C90.0269 (6)0.0348 (6)0.0475 (8)−0.0098 (5)−0.0022 (5)−0.0107 (5)
C100.0305 (7)0.0401 (7)0.0481 (8)−0.0147 (6)−0.0007 (6)−0.0060 (6)
C110.0324 (7)0.0423 (7)0.0411 (7)−0.0151 (6)−0.0007 (5)−0.0038 (6)
C120.0361 (7)0.0406 (7)0.0359 (7)−0.0157 (5)−0.0030 (5)−0.0061 (5)
C130.0392 (8)0.0658 (9)0.0350 (7)−0.0225 (7)−0.0019 (6)0.0012 (6)
C140.0371 (8)0.0610 (9)0.0463 (8)−0.0198 (7)0.0024 (6)−0.0028 (7)
C150.0645 (11)0.1003 (14)0.0435 (9)−0.0365 (11)−0.0114 (8)−0.0077 (9)
C160.0528 (10)0.0647 (10)0.0560 (10)−0.0123 (8)−0.0026 (8)0.0017 (8)
N10.0290 (6)0.0366 (6)0.0438 (6)−0.0120 (4)−0.0005 (5)−0.0075 (5)
N20.0311 (6)0.0424 (6)0.0447 (7)−0.0175 (5)−0.0040 (5)−0.0055 (5)
O10.0475 (6)0.0612 (6)0.0404 (6)−0.0314 (5)−0.0096 (4)0.0017 (4)
O20.0433 (6)0.0845 (8)0.0362 (6)−0.0261 (6)0.0033 (4)−0.0037 (5)
O30.0437 (6)0.0561 (6)0.0573 (7)−0.0265 (5)0.0087 (5)−0.0110 (5)
O40.0484 (6)0.0523 (6)0.0381 (5)−0.0292 (5)−0.0038 (4)0.0008 (4)
O50.0494 (7)0.1174 (11)0.0581 (7)−0.0452 (7)0.0062 (6)0.0067 (7)
Geometric parameters (Å, º) top
C1—N11.3095 (18)C10—H100.867 (19)
C1—N21.4107 (18)C11—C121.4483 (19)
C1—C21.412 (2)C11—C141.449 (2)
C2—C31.356 (2)C12—O41.2096 (17)
C2—H20.97 (2)C12—O11.3537 (17)
C3—C41.416 (2)C13—O21.4392 (18)
C3—H30.959 (18)C13—O11.4437 (17)
C4—C51.409 (2)C13—C161.499 (2)
C4—C91.410 (2)C13—C151.505 (2)
C5—C61.366 (3)C14—O51.208 (2)
C5—H50.94 (2)C14—O21.360 (2)
C6—C71.398 (3)C15—H15A0.9600
C6—H61.00 (2)C15—H15B0.9600
C7—C81.367 (2)C15—H15C0.9600
C7—H70.96 (2)C16—H16A0.9600
C8—O31.3608 (19)C16—H16B0.9600
C8—C91.4224 (19)C16—H16C0.9600
C9—N11.3644 (18)N2—H2N0.85 (2)
C10—N21.3255 (19)O3—H3O0.79 (2)
C10—C111.370 (2)
N1—C1—N2118.34 (12)C12—C11—C14119.95 (13)
N1—C1—C2124.55 (13)O4—C12—O1118.43 (12)
N2—C1—C2117.11 (12)O4—C12—C11124.72 (13)
C3—C2—C1118.21 (13)O1—C12—C11116.81 (11)
C3—C2—H2124.4 (10)O2—C13—O1109.88 (12)
C1—C2—H2117.4 (10)O2—C13—C16110.65 (14)
C2—C3—C4120.36 (14)O1—C13—C16110.18 (12)
C2—C3—H3122.0 (12)O2—C13—C15106.47 (13)
C4—C3—H3117.7 (12)O1—C13—C15106.14 (14)
C5—C4—C9119.49 (14)C16—C13—C15113.36 (15)
C5—C4—C3124.25 (14)O5—C14—O2118.07 (14)
C9—C4—C3116.25 (13)O5—C14—C11125.82 (15)
C6—C5—C4119.78 (16)O2—C14—C11116.05 (13)
C6—C5—H5119.4 (14)C13—C15—H15A109.5
C4—C5—H5120.7 (14)C13—C15—H15B109.5
C5—C6—C7121.53 (15)H15A—C15—H15B109.5
C5—C6—H6121.2 (12)C13—C15—H15C109.5
C7—C6—H6117.3 (12)H15A—C15—H15C109.5
C8—C7—C6119.85 (15)H15B—C15—H15C109.5
C8—C7—H7118.6 (11)C13—C16—H16A109.5
C6—C7—H7121.6 (11)C13—C16—H16B109.5
O3—C8—C7120.85 (14)H16A—C16—H16B109.5
O3—C8—C9118.76 (13)C13—C16—H16C109.5
C7—C8—C9120.38 (14)H16A—C16—H16C109.5
N1—C9—C4123.75 (12)H16B—C16—H16C109.5
N1—C9—C8117.29 (12)C1—N1—C9116.85 (12)
C4—C9—C8118.96 (13)C10—N2—C1124.05 (13)
N2—C10—C11125.99 (14)C10—N2—H2N119.6 (11)
N2—C10—H10116.6 (11)C1—N2—H2N116.4 (12)
C11—C10—H10117.4 (11)C12—O1—C13118.49 (11)
C10—C11—C12121.53 (13)C14—O2—C13118.71 (11)
C10—C11—C14118.32 (13)C8—O3—H3O107.0 (15)
N1—C1—C2—C31.0 (2)C10—C11—C12—O1174.03 (12)
N2—C1—C2—C3−179.08 (13)C14—C11—C12—O1−11.3 (2)
C1—C2—C3—C40.1 (2)C10—C11—C14—O58.0 (3)
C2—C3—C4—C5−179.85 (15)C12—C11—C14—O5−166.78 (17)
C2—C3—C4—C9−0.7 (2)C10—C11—C14—O2−174.86 (13)
C9—C4—C5—C60.6 (2)C12—C11—C14—O210.3 (2)
C3—C4—C5—C6179.72 (16)N2—C1—N1—C9178.78 (10)
C4—C5—C6—C70.2 (3)C2—C1—N1—C9−1.3 (2)
C5—C6—C7—C8−0.5 (3)C4—C9—N1—C10.58 (19)
C6—C7—C8—O3179.61 (13)C8—C9—N1—C1−178.91 (11)
C6—C7—C8—C90.1 (2)C11—C10—N2—C1−177.11 (13)
C5—C4—C9—N1179.58 (13)N1—C1—N2—C10−2.3 (2)
C3—C4—C9—N10.4 (2)C2—C1—N2—C10177.76 (12)
C5—C4—C9—C8−0.9 (2)O4—C12—O1—C13163.07 (13)
C3—C4—C9—C8179.84 (12)C11—C12—O1—C13−18.90 (18)
O3—C8—C9—N10.60 (18)O2—C13—O1—C1247.43 (17)
C7—C8—C9—N1−179.88 (12)C16—C13—O1—C12−74.74 (17)
O3—C8—C9—C4−178.92 (11)C15—C13—O1—C12162.17 (13)
C7—C8—C9—C40.6 (2)O5—C14—O2—C13−161.71 (16)
N2—C10—C11—C12−1.8 (2)C11—C14—O2—C1321.0 (2)
N2—C10—C11—C14−176.57 (13)O1—C13—O2—C14−48.65 (18)
C10—C11—C12—O4−8.1 (2)C16—C13—O2—C1473.23 (17)
C14—C11—C12—O4166.58 (13)C15—C13—O2—C14−163.18 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O40.85 (2)2.140 (19)2.7428 (17)127.6 (14)
N2—H2N···O4i0.85 (2)2.498 (18)3.2943 (17)156.2 (15)
O3—H3O···N10.79 (2)2.22 (2)2.7028 (16)120.0 (18)
C2—H2···O1i0.97 (2)2.564 (19)3.4151 (19)146.6 (14)
C2—H2···O4i0.97 (2)2.35 (2)3.2533 (19)155.4 (14)
Symmetry code: (i) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formulaC16H14N2O5
Mr314.29
Crystal system, space groupTriclinic, P1
Temperature (K)299
a, b, c (Å)7.445 (2), 8.440 (2), 12.906 (3)
α, β, γ (°)77.31 (1), 86.81 (2), 73.15 (1)
V (Å3)757.2 (3)
Z2
Radiation typeCu Kα
µ (mm−1)0.88
Crystal size (mm)0.60 × 0.40 × 0.33
Data collection
DiffractometerEnraf–Nonius CAD4
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		5325, 2704, 2436
Rint0.053
(sin θ/λ)max (Å−1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.120, 1.08
No. of reflections2704
No. of parameters233
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.27, −0.18

Computer programs: CAD-4-PC Software (Enraf–Nonius, 1996), CAD-4-PC Software, REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O40.85 (2)2.140 (19)2.7428 (17)127.6 (14)
N2—H2N···O4i0.85 (2)2.498 (18)3.2943 (17)156.2 (15)
O3—H3O···N10.79 (2)2.22 (2)2.7028 (16)120.0 (18)
C2—H2···O1i0.97 (2)2.564 (19)3.4151 (19)146.6 (14)
C2—H2···O4i0.97 (2)2.35 (2)3.2533 (19)155.4 (14)
Symmetry code: (i) −x+1, −y, −z+2.
 

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