organic compounds
2-Amino-4-(4-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 1,4-dioxane hemisolvate
aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, cUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and dChemistry Department, Faculty of Science, Sohag University, Sohag 82524, Egypt
*Correspondence e-mail: akkurt@erciyes.edu.tr
In the 17H16N2O3·0.5C4H8O2, pairs of N—H⋯N hydrogen bonds link molecules into dimers with R22(12) motifs, which are connected by N—H⋯O hydrogen bonds, forming a supramolecular array in the ab plane. The 1,4-dioxane ring, which lies about an inversion center, adopts a chair conformation.
of the title compound, CRelated literature
For the biological activity of pyran and fused-pyran molecules, see: Bargagna et al. (1992); Symeonidis et al. (2009); Narender & Gupta (2009); Alvey et al. (2009); Gorlitzer et al. (1984); Han et al. (2008); Martinez & Marco (1997); Smith et al. (1998); Taylor et al. (1998). For related structures, see: Gourdeau et al. (2004); Foroumadi et al. (2007); Mohamed et al. (2012). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; 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) and PLATON.
Supporting information
https://doi.org/10.1107/S1600536812027729/tk5115sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027729/tk5115Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812027729/tk5115Isup3.cml
A mixture of (4-methoxybenzylidene)propanedinitrile (184 mg, 1 mmol), cyclohexane-1,3-dione (112 mg, 1 mmol) in presence of ethanolamine (61 mg) as catalyst was refluxed in ethanol (50 ml). The reaction mixture was monitored by TLC until completion after 7 h. A solid product was deposited on cooling at ambient temperature and collected by filtration. The crude product was washed with dioxane and recrystallized from ethanol/drops of dioxane to afford the title compound in 78% yield. Single crystals suitable for X-ray analysis were grown up on slow evaporation of its mixed solvent ethanol/dioxane (9:1) solution at room temperature over three days. M.pt: 435 K.
All H atoms were positioned geometrically and refined by using a riding model, with N—H = 0.86 Å and C—H = 0.93 Å (aromatic), 0.96 Å (methyl), 0.97 Å (methylene) and 0.98 Å (methine), with Uiso(H) = 1.5Ueq(C) for methyl-H and Uiso(H) = 1.2Ueq(C, N) for other H-atoms.
Pyran and fused pyran ring systems are biologically interesting compounds known for their antimicrobial and antifungal (Alvey, et al., 2009), antioxidant (Symeonidis et al., 2009), antileishmanial (Narender et al., 2009), antitumor (Han et al., 2008). In addition, fused chromene ring systems have platelet antiaggregating, local anesthetic (Bargagna et al. 1992) and antihistaminic activities (Gorlitzer et al. 1984). They also exhibit inhibitory effects on influenza virus sialidases (Smith et al. 1998; Taylor et al. 1998) and antiviral activities (Martinez & Marco, 1997). Such observations prompted us to report the synthesis and
of the title compound (I).In (I), Fig. 1, the O2/C8—C10/C12/C13 4H-pyran and C12–C17 cyclohexene rings are puckered with puckering parameters (Cremer & Pople, 1975) of QT = 0.187 (2) Å, θ = 72.2 (5) °, φ = 175.7 (6) ° and QT = 0.455 (2) ° A, θ = 122.9 (3) °, φ = 48.5 (3) °, respectively. The centroid of the solvent 1,4-dioxane ring (O4/C18/C19/O4a/C18a/C19a) lies about an inversion center. The 1,4-dioxane ring adopts a chair conformation [puckering parameters QT = 0.560 (5) Å, θ = 3.46 (3) °, φ = 0.00 °]. The values of the bond lengths and angles in (I) are in normal ranges and are comparable with those of related structures (Gourdeau et al., 2004; Foroumadi et al., 2007; Mohamed et al., 2012).
In the crystal, molecules are linked by the pairs of N—H···N hydrogen bonds, forming dimers, with an R22(12) motif (Bernstein et al., 1995; Table 1, Fig. 2). These dimers are connected through the N—H···O hydrogen bonds with each other (Table 1, Fig. 2).
For the biological activity of pyran and fused-pyran molecules, see: Bargagna et al. (1992); Symeonidis et al. (2009); Narender & Gupta (2009); Alvey et al. (2009); Gorlitzer et al. (1984); Han et al. (2008); Martinez & Marco (1997); Smith et al. (1998); Taylor et al. (1998). For related structures, see: Gourdeau et al. (2004); Foroumadi et al. (2007); Mohamed et al. (2012). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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) and PLATON (Spek, 2009).C17H16N2O3·0.5C4H8O2 | Z = 2 |
Mr = 340.37 | F(000) = 360 |
Triclinic, P1 | Dx = 1.295 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0876 (4) Å | Cell parameters from 420 reflections |
b = 9.2013 (4) Å | θ = 3.6–22.5° |
c = 12.1613 (6) Å | µ = 0.09 mm−1 |
α = 94.376 (2)° | T = 293 K |
β = 102.827 (1)° | Prism, light-yellow |
γ = 95.972 (2)° | 0.35 × 0.25 × 0.22 mm |
V = 873.01 (7) Å3 |
Bruker Kappa APEXII CCD diffractometer | 4108 independent reflections |
Radiation source: fine-focus sealed tube | 3134 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
Detector resolution: 0.81 pixels mm-1 | θmax = 27.9°, θmin = 1.7° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −12→8 |
Tmin = 0.973, Tmax = 0.980 | l = −16→15 |
14186 measured 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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.194 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0997P)2 + 0.273P] where P = (Fo2 + 2Fc2)/3 |
4108 reflections | (Δ/σ)max < 0.001 |
227 parameters | Δρmax = 0.60 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
C17H16N2O3·0.5C4H8O2 | γ = 95.972 (2)° |
Mr = 340.37 | V = 873.01 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.0876 (4) Å | Mo Kα radiation |
b = 9.2013 (4) Å | µ = 0.09 mm−1 |
c = 12.1613 (6) Å | T = 293 K |
α = 94.376 (2)° | 0.35 × 0.25 × 0.22 mm |
β = 102.827 (1)° |
Bruker Kappa APEXII CCD diffractometer | 4108 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3134 reflections with I > 2σ(I) |
Tmin = 0.973, Tmax = 0.980 | Rint = 0.021 |
14186 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.194 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.60 e Å−3 |
4108 reflections | Δρmin = −0.39 e Å−3 |
227 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
O1 | 0.1813 (2) | 0.42680 (19) | 0.00491 (15) | 0.0760 (6) | |
O2 | 0.93204 (16) | 0.95097 (14) | 0.33842 (12) | 0.0512 (4) | |
O3 | 0.36871 (18) | 0.99158 (15) | 0.37001 (14) | 0.0595 (5) | |
N1 | 1.0877 (2) | 0.77420 (19) | 0.39337 (15) | 0.0563 (6) | |
N2 | 0.8057 (3) | 0.5088 (2) | 0.49805 (19) | 0.0712 (7) | |
C1 | 0.5009 (2) | 0.70436 (17) | 0.26984 (14) | 0.0389 (5) | |
C2 | 0.4984 (3) | 0.7302 (2) | 0.15944 (17) | 0.0531 (6) | |
C3 | 0.3939 (3) | 0.6405 (2) | 0.06812 (18) | 0.0583 (7) | |
C4 | 0.2893 (3) | 0.5219 (2) | 0.08782 (18) | 0.0537 (6) | |
C5 | 0.2917 (3) | 0.4941 (2) | 0.19793 (19) | 0.0563 (7) | |
C6 | 0.3951 (2) | 0.58441 (19) | 0.28771 (17) | 0.0476 (6) | |
C7 | 0.1568 (4) | 0.4634 (3) | −0.1082 (2) | 0.0809 (9) | |
C8 | 0.6180 (2) | 0.79962 (17) | 0.37058 (14) | 0.0387 (5) | |
C9 | 0.7912 (2) | 0.74660 (18) | 0.40311 (14) | 0.0405 (5) | |
C10 | 0.9333 (2) | 0.81758 (19) | 0.38054 (14) | 0.0420 (5) | |
C11 | 0.8019 (2) | 0.6148 (2) | 0.45477 (17) | 0.0487 (6) | |
C12 | 0.7895 (2) | 1.02140 (18) | 0.33096 (14) | 0.0422 (5) | |
C13 | 0.6429 (2) | 0.95783 (18) | 0.34927 (14) | 0.0403 (5) | |
C14 | 0.5022 (2) | 1.04491 (19) | 0.35100 (15) | 0.0461 (6) | |
C15 | 0.5308 (3) | 1.2042 (2) | 0.3328 (2) | 0.0634 (8) | |
C16 | 0.6528 (3) | 1.2323 (2) | 0.2563 (2) | 0.0660 (8) | |
C17 | 0.8203 (3) | 1.1737 (2) | 0.29963 (18) | 0.0537 (6) | |
O4 | 0.8992 (4) | 0.9746 (4) | 1.0758 (2) | 0.1475 (16) | |
C18 | 0.8279 (5) | 0.9756 (5) | 0.9615 (4) | 0.1243 (19) | |
C19 | 0.9322 (6) | 1.0707 (6) | 0.9113 (4) | 0.138 (2) | |
H1A | 1.10620 | 0.69140 | 0.41900 | 0.0680* | |
H1B | 1.16900 | 0.82900 | 0.37610 | 0.0680* | |
H2 | 0.56870 | 0.81000 | 0.14570 | 0.0640* | |
H3 | 0.39450 | 0.66020 | −0.00570 | 0.0700* | |
H5 | 0.22270 | 0.41340 | 0.21170 | 0.0680* | |
H6 | 0.39390 | 0.56470 | 0.36140 | 0.0570* | |
H7A | 0.11860 | 0.55860 | −0.11240 | 0.1210* | |
H7B | 0.07240 | 0.39170 | −0.15710 | 0.1210* | |
H7C | 0.26270 | 0.46480 | −0.13150 | 0.1210* | |
H8 | 0.56480 | 0.79380 | 0.43530 | 0.0460* | |
H15A | 0.57660 | 1.26170 | 0.40550 | 0.0760* | |
H15B | 0.42210 | 1.23650 | 0.29930 | 0.0760* | |
H16A | 0.60040 | 1.18570 | 0.18050 | 0.0790* | |
H16B | 0.67420 | 1.33710 | 0.25170 | 0.0790* | |
H17A | 0.88530 | 1.17380 | 0.24150 | 0.0640* | |
H17B | 0.88670 | 1.23700 | 0.36540 | 0.0640* | |
H18A | 0.71550 | 1.00780 | 0.95170 | 0.1500* | |
H18B | 0.81450 | 0.87690 | 0.92390 | 0.1500* | |
H19A | 0.94160 | 1.17020 | 0.94680 | 0.1660* | |
H19B | 0.87970 | 1.07000 | 0.83140 | 0.1660* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0761 (11) | 0.0640 (10) | 0.0702 (10) | −0.0133 (8) | −0.0058 (8) | −0.0056 (8) |
O2 | 0.0475 (7) | 0.0467 (7) | 0.0657 (8) | 0.0030 (5) | 0.0229 (6) | 0.0207 (6) |
O3 | 0.0480 (8) | 0.0506 (8) | 0.0832 (10) | 0.0060 (6) | 0.0217 (7) | 0.0084 (7) |
N1 | 0.0429 (9) | 0.0552 (10) | 0.0748 (11) | 0.0057 (7) | 0.0169 (8) | 0.0229 (8) |
N2 | 0.0600 (11) | 0.0595 (11) | 0.1025 (16) | 0.0096 (8) | 0.0244 (10) | 0.0413 (11) |
C1 | 0.0359 (8) | 0.0347 (8) | 0.0472 (9) | 0.0047 (6) | 0.0112 (7) | 0.0063 (6) |
C2 | 0.0594 (12) | 0.0473 (10) | 0.0514 (10) | −0.0082 (8) | 0.0170 (9) | 0.0062 (8) |
C3 | 0.0649 (13) | 0.0591 (12) | 0.0475 (10) | −0.0043 (10) | 0.0117 (9) | 0.0042 (9) |
C4 | 0.0487 (11) | 0.0441 (10) | 0.0612 (12) | 0.0022 (8) | 0.0016 (9) | −0.0009 (8) |
C5 | 0.0505 (11) | 0.0417 (10) | 0.0702 (13) | −0.0070 (8) | 0.0040 (9) | 0.0124 (9) |
C6 | 0.0454 (10) | 0.0423 (9) | 0.0543 (10) | 0.0002 (7) | 0.0091 (8) | 0.0148 (8) |
C7 | 0.0762 (17) | 0.0896 (18) | 0.0618 (14) | 0.0016 (13) | −0.0056 (12) | −0.0107 (13) |
C8 | 0.0407 (8) | 0.0354 (8) | 0.0418 (8) | 0.0004 (6) | 0.0145 (7) | 0.0071 (6) |
C9 | 0.0423 (9) | 0.0372 (8) | 0.0413 (8) | 0.0004 (6) | 0.0085 (7) | 0.0087 (6) |
C10 | 0.0443 (9) | 0.0398 (8) | 0.0414 (8) | 0.0015 (7) | 0.0092 (7) | 0.0082 (7) |
C11 | 0.0413 (9) | 0.0462 (10) | 0.0586 (11) | 0.0016 (7) | 0.0104 (8) | 0.0144 (8) |
C12 | 0.0499 (10) | 0.0354 (8) | 0.0420 (9) | 0.0005 (7) | 0.0133 (7) | 0.0070 (7) |
C13 | 0.0460 (9) | 0.0341 (8) | 0.0407 (8) | 0.0008 (7) | 0.0114 (7) | 0.0049 (6) |
C14 | 0.0494 (10) | 0.0393 (9) | 0.0481 (10) | 0.0031 (7) | 0.0091 (8) | 0.0041 (7) |
C15 | 0.0664 (13) | 0.0403 (10) | 0.0882 (16) | 0.0107 (9) | 0.0234 (12) | 0.0150 (10) |
C16 | 0.0820 (16) | 0.0462 (11) | 0.0748 (14) | 0.0089 (10) | 0.0219 (12) | 0.0245 (10) |
C17 | 0.0659 (12) | 0.0391 (9) | 0.0605 (11) | −0.0019 (8) | 0.0251 (10) | 0.0135 (8) |
O4 | 0.125 (2) | 0.236 (4) | 0.0879 (17) | 0.028 (2) | 0.0352 (16) | 0.018 (2) |
C18 | 0.105 (3) | 0.152 (4) | 0.107 (3) | 0.002 (3) | 0.010 (2) | 0.020 (3) |
C19 | 0.114 (3) | 0.200 (5) | 0.111 (3) | 0.038 (3) | 0.022 (2) | 0.069 (3) |
O1—C4 | 1.364 (3) | C13—C14 | 1.461 (2) |
O1—C7 | 1.417 (3) | C14—C15 | 1.501 (3) |
O2—C10 | 1.366 (2) | C15—C16 | 1.516 (3) |
O2—C12 | 1.369 (2) | C16—C17 | 1.511 (3) |
O3—C14 | 1.216 (2) | C2—H2 | 0.9300 |
O4—C18 | 1.383 (5) | C3—H3 | 0.9300 |
O4—C19i | 1.446 (6) | C5—H5 | 0.9300 |
N1—C10 | 1.330 (2) | C6—H6 | 0.9300 |
N2—C11 | 1.143 (3) | C7—H7C | 0.9600 |
N1—H1B | 0.8600 | C7—H7A | 0.9600 |
N1—H1A | 0.8600 | C7—H7B | 0.9600 |
C1—C2 | 1.377 (3) | C8—H8 | 0.9800 |
C1—C8 | 1.521 (2) | C15—H15B | 0.9700 |
C1—C6 | 1.386 (2) | C15—H15A | 0.9700 |
C2—C3 | 1.388 (3) | C16—H16A | 0.9700 |
C3—C4 | 1.379 (3) | C16—H16B | 0.9700 |
C4—C5 | 1.379 (3) | C17—H17B | 0.9700 |
C5—C6 | 1.376 (3) | C17—H17A | 0.9700 |
C8—C13 | 1.499 (2) | C18—C19 | 1.417 (7) |
C8—C9 | 1.511 (2) | C18—H18A | 0.9700 |
C9—C10 | 1.354 (2) | C18—H18B | 0.9700 |
C9—C11 | 1.410 (3) | C19—H19A | 0.9700 |
C12—C13 | 1.338 (2) | C19—H19B | 0.9700 |
C12—C17 | 1.491 (3) | ||
C4—O1—C7 | 117.78 (19) | C2—C3—H3 | 120.00 |
C10—O2—C12 | 118.91 (14) | C6—C5—H5 | 120.00 |
C18—O4—C19i | 108.6 (3) | C4—C5—H5 | 120.00 |
H1A—N1—H1B | 120.00 | C1—C6—H6 | 120.00 |
C10—N1—H1B | 120.00 | C5—C6—H6 | 120.00 |
C10—N1—H1A | 120.00 | O1—C7—H7A | 109.00 |
C2—C1—C6 | 117.77 (17) | O1—C7—H7B | 109.00 |
C6—C1—C8 | 119.84 (15) | H7A—C7—H7B | 109.00 |
C2—C1—C8 | 122.37 (15) | H7A—C7—H7C | 109.00 |
C1—C2—C3 | 121.88 (19) | H7B—C7—H7C | 110.00 |
C2—C3—C4 | 119.41 (19) | O1—C7—H7C | 109.00 |
O1—C4—C5 | 116.23 (19) | C9—C8—H8 | 108.00 |
C3—C4—C5 | 119.3 (2) | C13—C8—H8 | 108.00 |
O1—C4—C3 | 124.49 (19) | C1—C8—H8 | 108.00 |
C4—C5—C6 | 120.73 (19) | C14—C15—H15B | 109.00 |
C1—C6—C5 | 120.93 (18) | C16—C15—H15A | 109.00 |
C9—C8—C13 | 108.63 (14) | C16—C15—H15B | 109.00 |
C1—C8—C13 | 112.38 (14) | H15A—C15—H15B | 108.00 |
C1—C8—C9 | 111.95 (13) | C14—C15—H15A | 109.00 |
C8—C9—C10 | 122.54 (15) | C15—C16—H16B | 109.00 |
C10—C9—C11 | 119.42 (16) | C17—C16—H16A | 109.00 |
C8—C9—C11 | 118.00 (14) | C15—C16—H16A | 109.00 |
O2—C10—N1 | 110.30 (15) | H16A—C16—H16B | 108.00 |
N1—C10—C9 | 128.22 (17) | C17—C16—H16B | 109.00 |
O2—C10—C9 | 121.48 (15) | C12—C17—H17A | 110.00 |
N2—C11—C9 | 177.6 (2) | C12—C17—H17B | 110.00 |
O2—C12—C13 | 122.91 (15) | C16—C17—H17B | 110.00 |
C13—C12—C17 | 125.75 (17) | H17A—C17—H17B | 108.00 |
O2—C12—C17 | 111.34 (16) | C16—C17—H17A | 110.00 |
C8—C13—C14 | 118.19 (14) | O4—C18—C19 | 110.9 (4) |
C8—C13—C12 | 122.27 (15) | O4i—C19—C18 | 110.8 (4) |
C12—C13—C14 | 119.54 (15) | O4—C18—H18A | 109.00 |
C13—C14—C15 | 117.57 (16) | O4—C18—H18B | 109.00 |
O3—C14—C13 | 121.28 (16) | C19—C18—H18A | 109.00 |
O3—C14—C15 | 121.11 (17) | C19—C18—H18B | 109.00 |
C14—C15—C16 | 112.24 (17) | H18A—C18—H18B | 108.00 |
C15—C16—C17 | 111.57 (18) | C18—C19—H19A | 109.00 |
C12—C17—C16 | 110.51 (18) | C18—C19—H19B | 109.00 |
C1—C2—H2 | 119.00 | H19A—C19—H19B | 108.00 |
C3—C2—H2 | 119.00 | O4i—C19—H19A | 109.00 |
C4—C3—H3 | 120.00 | O4i—C19—H19B | 110.00 |
C7—O1—C4—C3 | −9.3 (3) | C1—C8—C9—C10 | 105.99 (18) |
C7—O1—C4—C5 | 171.1 (2) | C1—C8—C9—C11 | −71.4 (2) |
C10—O2—C12—C17 | 171.59 (15) | C9—C8—C13—C14 | −161.46 (15) |
C12—O2—C10—N1 | −172.95 (15) | C1—C8—C13—C14 | 74.12 (19) |
C10—O2—C12—C13 | −8.8 (2) | C9—C8—C13—C12 | 17.3 (2) |
C12—O2—C10—C9 | 7.4 (2) | C11—C9—C10—N1 | 5.4 (3) |
C18i—O4i—C19—C18 | −58.0 (5) | C8—C9—C10—O2 | 7.6 (3) |
C19i—O4—C18—C19 | −58.0 (5) | C8—C9—C10—N1 | −172.00 (17) |
C8—C1—C2—C3 | 178.46 (19) | C11—C9—C10—O2 | −175.05 (16) |
C8—C1—C6—C5 | −178.09 (17) | C17—C12—C13—C8 | 174.55 (17) |
C2—C1—C6—C5 | 0.2 (3) | C17—C12—C13—C14 | −6.7 (3) |
C2—C1—C8—C9 | −87.6 (2) | O2—C12—C17—C16 | 162.26 (16) |
C2—C1—C8—C13 | 34.9 (2) | C13—C12—C17—C16 | −17.3 (3) |
C6—C1—C8—C9 | 90.63 (19) | O2—C12—C13—C14 | 173.82 (15) |
C6—C1—C8—C13 | −146.80 (16) | O2—C12—C13—C8 | −5.0 (3) |
C6—C1—C2—C3 | 0.2 (3) | C12—C13—C14—O3 | −178.26 (18) |
C1—C2—C3—C4 | 0.0 (3) | C8—C13—C14—O3 | 0.6 (3) |
C2—C3—C4—C5 | −0.5 (3) | C12—C13—C14—C15 | −0.5 (3) |
C2—C3—C4—O1 | 179.8 (2) | C8—C13—C14—C15 | 178.31 (16) |
O1—C4—C5—C6 | −179.37 (19) | O3—C14—C15—C16 | −151.3 (2) |
C3—C4—C5—C6 | 1.0 (3) | C13—C14—C15—C16 | 31.0 (3) |
C4—C5—C6—C1 | −0.8 (3) | C14—C15—C16—C17 | −54.6 (2) |
C13—C8—C9—C11 | 163.92 (15) | C15—C16—C17—C12 | 46.9 (2) |
C1—C8—C13—C12 | −107.09 (18) | O4—C18—C19—O4i | 59.3 (5) |
C13—C8—C9—C10 | −18.7 (2) |
Symmetry code: (i) −x+2, −y+2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N2ii | 0.86 | 2.27 | 3.123 (3) | 171 |
N1—H1B···O3iii | 0.86 | 2.10 | 2.945 (2) | 167 |
Symmetry codes: (ii) −x+2, −y+1, −z+1; (iii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C17H16N2O3·0.5C4H8O2 |
Mr | 340.37 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.0876 (4), 9.2013 (4), 12.1613 (6) |
α, β, γ (°) | 94.376 (2), 102.827 (1), 95.972 (2) |
V (Å3) | 873.01 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.35 × 0.25 × 0.22 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.973, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14186, 4108, 3134 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.659 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.194, 1.07 |
No. of reflections | 4108 |
No. of parameters | 227 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.60, −0.39 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N2i | 0.86 | 2.27 | 3.123 (3) | 171 |
N1—H1B···O3ii | 0.86 | 2.10 | 2.945 (2) | 167 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y, z. |
Acknowledgements
We thank Manchester Metropolitan University, the University of Sargodha and Erciyes University for guidance and for instrumental support of this study. We also extend our thanks to the Egyptian Government for their financial support of this project.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Pyran and fused pyran ring systems are biologically interesting compounds known for their antimicrobial and antifungal (Alvey, et al., 2009), antioxidant (Symeonidis et al., 2009), antileishmanial (Narender et al., 2009), antitumor (Han et al., 2008). In addition, fused chromene ring systems have platelet antiaggregating, local anesthetic (Bargagna et al. 1992) and antihistaminic activities (Gorlitzer et al. 1984). They also exhibit inhibitory effects on influenza virus sialidases (Smith et al. 1998; Taylor et al. 1998) and antiviral activities (Martinez & Marco, 1997). Such observations prompted us to report the synthesis and crystal structure of the title compound (I).
In (I), Fig. 1, the O2/C8—C10/C12/C13 4H-pyran and C12–C17 cyclohexene rings are puckered with puckering parameters (Cremer & Pople, 1975) of QT = 0.187 (2) Å, θ = 72.2 (5) °, φ = 175.7 (6) ° and QT = 0.455 (2) ° A, θ = 122.9 (3) °, φ = 48.5 (3) °, respectively. The centroid of the solvent 1,4-dioxane ring (O4/C18/C19/O4a/C18a/C19a) lies about an inversion center. The 1,4-dioxane ring adopts a chair conformation [puckering parameters QT = 0.560 (5) Å, θ = 3.46 (3) °, φ = 0.00 °]. The values of the bond lengths and angles in (I) are in normal ranges and are comparable with those of related structures (Gourdeau et al., 2004; Foroumadi et al., 2007; Mohamed et al., 2012).
In the crystal, molecules are linked by the pairs of N—H···N hydrogen bonds, forming dimers, with an R22(12) motif (Bernstein et al., 1995; Table 1, Fig. 2). These dimers are connected through the N—H···O hydrogen bonds with each other (Table 1, Fig. 2).