organic compounds
2-Amino-4-(4-methoxyphenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile propan-2-one monosolvate
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 dDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan
*Correspondence e-mail: akkurt@erciyes.edu.tr
In the 19H20N2O3·C3H6O, molecules are linked into inversion dimers with an R22(12) motif by pairs of N—H⋯N hydrogen bonds. These dimers are further connected into chains running along the a axis by N—H⋯O hydrogen bonds. C—H⋯N and C—H⋯π interactions also feature in the packing. The cyclohexene ring adopts nearly an [puckering parameters are QT = 0.456 (2) Å, θ = 54.6 (3)° and φ = 225.2 (3)°].
of the title compound, CRelated literature
For pharmacological properties of 4H-chromene and fused 4H-chromene derivatives, see: Kemnitzer et al. (2007, 2008); Abd-El-Aziz et al. (2004, 2007); Sabry et al. (2011); Gourdeau et al. (2004); Mahdavi et al. (2011); Brühlmann et al. (2001). For a related structure, see: 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/S160053681202781X/bt5943sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681202781X/bt5943Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S160053681202781X/bt5943Isup3.cml
To a solution of 184 mg (1 mmol) (4-methoxybenzylidene)propanedinitrile in 50 ml ethanol, 140 mg (1 mmol) 5,5-dimethylcyclohexane-1,3-dione was added in presence of 123 mg (1 mmol) (4-aminophenyl)methanol as catalyst. The reaction mixture was refluxed at 350 K for 5 h, then cooled at ambient temperature. The resin product that formed was solidified by washing with acetone then filtered off under vacuum and recrystallized from ethanol. Single crystals suitable for X-ray diffraction were produced by slow evaporation of ethanol/acetone solution (1:1) of (I) over two days at room temperature. Yield is 86%, M.p. 443 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(O) for methyl groups and Uiso(H) = 1.2Ueq(C, N) for others.
Compounds such as 4H-chromenes and fused 4H-chromenes are a great class of organic drugs due to their wide applications in chemo therapy. They exhibited anticancer activities (Kemnitzer et al., 2007, 2008; Abd-El-Aziz et al., 2004, 2007; Gourdeau et al., 2004; Sabry et al., 2011; Mahdavi et al., 2011) and have used in treatment of Alzheimer's disease and Schizophrenia disorder (Brühlmann et al., 2001). In this context and further to our on-going study in synthesis and biological investigation of 4H-chromene compounds (Mohamed et al. 2012), we report in this study the structure and synthesis of the title compound (I).
In the title compound (I) shown in Fig. 1, the C12–C17 cyclohexene and O2/C8—C10/C12/C13 4H-pyran rings are puckered with the puckering parameters (Cremer & Pople, 1975) of QT = 0.456 (2) ° A, θ = 54.6 (3) °, φ = 225.2 (3) °, and QT = 0.201 (2) Å, θ = 108.1 (5) °, φ = 354.7 (6) °, respectively. The bond lengths and bond angles in (I) are normal and are comparable with those of a related structure previously reported (Mohamed et al., 2012).
In the π interactions contribute to the stabilization of the crystal packing (Table 1, Fig. 2).
adjacent molecules are connected 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 further connected to chains running along the a axis by N—H···O hydrogen bonds. Furthermore, C—H···For pharmacological properties of 4H-chromene and fused 4H-chromene derivatives, see: Kemnitzer et al. (2007, 2008); Abd-El-Aziz et al. (2004, 2007); Sabry et al. (2011); Gourdeau et al. (2004); Mahdavi et al. (2011); Brühlmann et al. (2001). For a related structure, see: 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).Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. | |
Fig. 2. View of the dimers formed by pairs of N—H···N hydrogen bonds, with an R22(12) motif and the N—H···O and C—H···N hydrogen bonds connect the dimers with each other. H atoms not involved in hydrogen bonds have been omitted for clarity. |
C19H20N2O3·C3H6O | Z = 2 |
Mr = 382.45 | F(000) = 408 |
Triclinic, P1 | Dx = 1.217 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2037 (4) Å | Cell parameters from 360 reflections |
b = 9.5319 (4) Å | θ = 21.3–3.4° |
c = 13.8390 (7) Å | µ = 0.08 mm−1 |
α = 77.743 (2)° | T = 296 K |
β = 87.307 (3)° | Prism, white |
γ = 80.672 (2)° | 0.28 × 0.22 × 0.20 mm |
V = 1043.43 (9) Å3 |
Bruker Kappa APEXII CCD diffractometer | 4917 independent reflections |
Radiation source: fine-focus sealed tube | 3284 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 0.81 pixels mm-1 | θmax = 28.0°, θmin = 2.2° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −12→9 |
Tmin = 0.978, Tmax = 0.983 | l = −18→18 |
16752 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) = 0.182 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0878P)2 + 0.2431P] where P = (Fo2 + 2Fc2)/3 |
4917 reflections | (Δ/σ)max < 0.001 |
246 parameters | Δρmax = 0.59 e Å−3 |
1 restraint | Δρmin = −0.50 e Å−3 |
C19H20N2O3·C3H6O | γ = 80.672 (2)° |
Mr = 382.45 | V = 1043.43 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.2037 (4) Å | Mo Kα radiation |
b = 9.5319 (4) Å | µ = 0.08 mm−1 |
c = 13.8390 (7) Å | T = 296 K |
α = 77.743 (2)° | 0.28 × 0.22 × 0.20 mm |
β = 87.307 (3)° |
Bruker Kappa APEXII CCD diffractometer | 4917 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3284 reflections with I > 2σ(I) |
Tmin = 0.978, Tmax = 0.983 | Rint = 0.027 |
16752 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 1 restraint |
wR(F2) = 0.182 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.59 e Å−3 |
4917 reflections | Δρmin = −0.50 e Å−3 |
246 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 | 0.4032 (2) | 0.66247 (19) | 0.08006 (13) | 0.0802 (7) | |
O2 | 1.02042 (14) | 0.08753 (13) | 0.35411 (10) | 0.0488 (4) | |
O3 | 0.45650 (17) | 0.03885 (16) | 0.37857 (13) | 0.0629 (6) | |
N1 | 0.8196 (2) | 0.4700 (2) | 0.51973 (16) | 0.0656 (7) | |
N2 | 1.14500 (19) | 0.24295 (18) | 0.41136 (14) | 0.0563 (6) | |
C1 | 0.6070 (2) | 0.33700 (18) | 0.31182 (14) | 0.0399 (5) | |
C2 | 0.6619 (2) | 0.3463 (2) | 0.21430 (15) | 0.0483 (6) | |
C3 | 0.5919 (3) | 0.4548 (2) | 0.13983 (16) | 0.0543 (7) | |
C4 | 0.4642 (3) | 0.5588 (2) | 0.16012 (16) | 0.0532 (7) | |
C5 | 0.4076 (2) | 0.5523 (2) | 0.25594 (17) | 0.0549 (7) | |
C6 | 0.4797 (2) | 0.4416 (2) | 0.33068 (15) | 0.0473 (6) | |
C7 | 0.2741 (4) | 0.7714 (3) | 0.0945 (2) | 0.0952 (11) | |
C8 | 0.6896 (2) | 0.22102 (18) | 0.39559 (14) | 0.0389 (5) | |
C9 | 0.8474 (2) | 0.26366 (19) | 0.42629 (14) | 0.0437 (4) | |
C10 | 0.9993 (2) | 0.20384 (19) | 0.39964 (14) | 0.0419 (5) | |
C11 | 0.8333 (2) | 0.37739 (19) | 0.47771 (14) | 0.0437 (4) | |
C12 | 0.8867 (2) | 0.02105 (18) | 0.34609 (14) | 0.0408 (5) | |
C13 | 0.7325 (2) | 0.07535 (18) | 0.36796 (13) | 0.0403 (5) | |
C14 | 0.5994 (2) | −0.00856 (19) | 0.36226 (15) | 0.0455 (6) | |
C15 | 0.6483 (2) | −0.1573 (2) | 0.33914 (17) | 0.0538 (7) | |
C16 | 0.7957 (3) | −0.1685 (2) | 0.26744 (17) | 0.0570 (5) | |
C17 | 0.9388 (2) | −0.11592 (19) | 0.30923 (16) | 0.0475 (6) | |
C18 | 0.8500 (3) | −0.3269 (2) | 0.2591 (2) | 0.0702 (9) | |
C19 | 0.7493 (3) | −0.0761 (2) | 0.16615 (17) | 0.0570 (5) | |
O4 | 0.0402 (4) | 0.1650 (4) | 0.0951 (3) | 0.1652 (16) | |
C20 | 0.1432 (4) | 0.2327 (4) | 0.1086 (2) | 0.0875 (11) | |
C21 | 0.3163 (5) | 0.1707 (5) | 0.1206 (4) | 0.149 (2) | |
C22 | 0.1030 (5) | 0.3830 (4) | 0.1273 (4) | 0.142 (2) | |
H2 | 0.74790 | 0.27740 | 0.19950 | 0.0580* | |
H2A | 1.14960 | 0.31490 | 0.43900 | 0.0680* | |
H2B | 1.23420 | 0.19620 | 0.39120 | 0.0680* | |
H3 | 0.63040 | 0.45860 | 0.07520 | 0.0650* | |
H5 | 0.32180 | 0.62150 | 0.27050 | 0.0660* | |
H6 | 0.44110 | 0.43780 | 0.39530 | 0.0570* | |
H7A | 0.18230 | 0.72780 | 0.12580 | 0.1420* | |
H7B | 0.24060 | 0.83210 | 0.03180 | 0.1420* | |
H7C | 0.31060 | 0.82910 | 0.13580 | 0.1420* | |
H8 | 0.61350 | 0.21200 | 0.45250 | 0.0470* | |
H15A | 0.55440 | −0.18350 | 0.31090 | 0.0650* | |
H15B | 0.67530 | −0.22710 | 0.40040 | 0.0650* | |
H17A | 0.98780 | −0.19130 | 0.36310 | 0.0570* | |
H17B | 1.02270 | −0.10000 | 0.25810 | 0.0570* | |
H18A | 0.75920 | −0.36330 | 0.23680 | 0.1050* | |
H18B | 0.88460 | −0.38430 | 0.32260 | 0.1050* | |
H18C | 0.94030 | −0.33260 | 0.21270 | 0.1050* | |
H19A | 0.71430 | 0.02300 | 0.17170 | 0.0850* | |
H19B | 0.66090 | −0.11140 | 0.14030 | 0.0850* | |
H19C | 0.84340 | −0.08150 | 0.12240 | 0.0850* | |
H21A | 0.35150 | 0.17590 | 0.18470 | 0.2240* | |
H21B | 0.38070 | 0.22410 | 0.07060 | 0.2240* | |
H21C | 0.33130 | 0.07090 | 0.11440 | 0.2240* | |
H22A | 0.15880 | 0.44750 | 0.07910 | 0.2140* | |
H22B | 0.13850 | 0.38360 | 0.19230 | 0.2140* | |
H22C | −0.01410 | 0.41450 | 0.12260 | 0.2140* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0853 (12) | 0.0744 (11) | 0.0695 (11) | 0.0109 (9) | −0.0079 (9) | −0.0055 (9) |
O2 | 0.0325 (6) | 0.0517 (7) | 0.0730 (9) | −0.0094 (5) | 0.0028 (6) | −0.0355 (7) |
O3 | 0.0363 (7) | 0.0646 (9) | 0.0955 (12) | −0.0134 (6) | 0.0069 (7) | −0.0313 (8) |
N1 | 0.0476 (10) | 0.0739 (12) | 0.0915 (14) | −0.0128 (9) | 0.0111 (9) | −0.0534 (11) |
N2 | 0.0338 (8) | 0.0609 (10) | 0.0875 (13) | −0.0101 (7) | −0.0002 (8) | −0.0433 (9) |
C1 | 0.0310 (8) | 0.0410 (9) | 0.0535 (11) | −0.0093 (7) | 0.0008 (7) | −0.0203 (8) |
C2 | 0.0443 (10) | 0.0474 (10) | 0.0576 (12) | −0.0066 (8) | 0.0043 (9) | −0.0224 (9) |
C3 | 0.0581 (12) | 0.0571 (11) | 0.0512 (12) | −0.0099 (10) | 0.0041 (10) | −0.0193 (9) |
C4 | 0.0499 (11) | 0.0530 (11) | 0.0580 (13) | −0.0082 (9) | −0.0084 (10) | −0.0128 (9) |
C5 | 0.0408 (10) | 0.0538 (11) | 0.0708 (14) | 0.0020 (8) | −0.0011 (9) | −0.0216 (10) |
C6 | 0.0367 (9) | 0.0521 (10) | 0.0557 (12) | −0.0056 (8) | 0.0043 (8) | −0.0189 (9) |
C7 | 0.093 (2) | 0.0738 (17) | 0.101 (2) | 0.0192 (15) | −0.0154 (17) | −0.0002 (15) |
C8 | 0.0314 (8) | 0.0416 (9) | 0.0480 (10) | −0.0077 (7) | 0.0039 (7) | −0.0184 (7) |
C9 | 0.0351 (7) | 0.0473 (7) | 0.0538 (8) | −0.0064 (5) | 0.0003 (6) | −0.0222 (6) |
C10 | 0.0381 (9) | 0.0428 (9) | 0.0505 (10) | −0.0070 (7) | −0.0030 (8) | −0.0214 (8) |
C11 | 0.0351 (7) | 0.0473 (7) | 0.0538 (8) | −0.0064 (5) | 0.0003 (6) | −0.0222 (6) |
C12 | 0.0355 (9) | 0.0407 (9) | 0.0504 (10) | −0.0082 (7) | −0.0015 (8) | −0.0172 (8) |
C13 | 0.0350 (9) | 0.0401 (9) | 0.0484 (10) | −0.0073 (7) | −0.0005 (7) | −0.0142 (7) |
C14 | 0.0388 (10) | 0.0458 (9) | 0.0553 (11) | −0.0118 (8) | 0.0007 (8) | −0.0145 (8) |
C15 | 0.0479 (11) | 0.0469 (10) | 0.0738 (14) | −0.0187 (8) | 0.0022 (10) | −0.0208 (9) |
C16 | 0.0577 (9) | 0.0558 (8) | 0.0649 (9) | −0.0136 (7) | −0.0035 (7) | −0.0248 (7) |
C17 | 0.0408 (10) | 0.0410 (9) | 0.0656 (13) | −0.0045 (7) | −0.0014 (9) | −0.0233 (9) |
C18 | 0.0664 (14) | 0.0530 (12) | 0.1049 (19) | −0.0192 (10) | 0.0059 (13) | −0.0410 (13) |
C19 | 0.0577 (9) | 0.0558 (8) | 0.0649 (9) | −0.0136 (7) | −0.0035 (7) | −0.0248 (7) |
O4 | 0.118 (2) | 0.219 (3) | 0.206 (3) | −0.089 (2) | 0.007 (2) | −0.104 (3) |
C20 | 0.0769 (19) | 0.110 (2) | 0.090 (2) | −0.0446 (17) | 0.0029 (15) | −0.0312 (17) |
C21 | 0.092 (3) | 0.125 (3) | 0.237 (6) | −0.014 (2) | −0.018 (3) | −0.049 (4) |
C22 | 0.115 (3) | 0.115 (3) | 0.199 (5) | −0.032 (2) | 0.019 (3) | −0.031 (3) |
O1—C4 | 1.372 (3) | C16—C18 | 1.531 (3) |
O1—C7 | 1.397 (4) | C2—H2 | 0.9300 |
O2—C10 | 1.371 (2) | C3—H3 | 0.9300 |
O2—C12 | 1.373 (2) | C5—H5 | 0.9300 |
O3—C14 | 1.215 (2) | C6—H6 | 0.9300 |
O4—C20 | 1.187 (5) | C7—H7B | 0.9600 |
N1—C11 | 1.144 (3) | C7—H7C | 0.9600 |
N2—C10 | 1.335 (2) | C7—H7A | 0.9600 |
N2—H2B | 0.8600 | C8—H8 | 0.9800 |
N2—H2A | 0.8600 | C15—H15B | 0.9700 |
C1—C2 | 1.392 (3) | C15—H15A | 0.9700 |
C1—C8 | 1.521 (3) | C17—H17A | 0.9700 |
C1—C6 | 1.379 (3) | C17—H17B | 0.9700 |
C2—C3 | 1.368 (3) | C18—H18B | 0.9600 |
C3—C4 | 1.383 (3) | C18—H18C | 0.9600 |
C4—C5 | 1.376 (3) | C18—H18A | 0.9600 |
C5—C6 | 1.387 (3) | C19—H19B | 0.9600 |
C8—C9 | 1.522 (2) | C19—H19C | 0.9600 |
C8—C13 | 1.501 (2) | C19—H19A | 0.9600 |
C9—C10 | 1.353 (2) | C20—C21 | 1.450 (5) |
C9—C11 | 1.405 (3) | C20—C22 | 1.492 (5) |
C12—C13 | 1.333 (2) | C21—H21A | 0.9600 |
C12—C17 | 1.493 (3) | C21—H21B | 0.9600 |
C13—C14 | 1.468 (2) | C21—H21C | 0.9600 |
C14—C15 | 1.507 (3) | C22—H22A | 0.9600 |
C15—C16 | 1.533 (3) | C22—H22B | 0.9600 |
C16—C19 | 1.518 (3) | C22—H22C | 0.9600 |
C16—C17 | 1.530 (3) | ||
C4—O1—C7 | 119.00 (19) | C1—C6—H6 | 119.00 |
C10—O2—C12 | 118.71 (13) | C5—C6—H6 | 119.00 |
C10—N2—H2B | 120.00 | O1—C7—H7A | 109.00 |
H2A—N2—H2B | 120.00 | O1—C7—H7B | 109.00 |
C10—N2—H2A | 120.00 | O1—C7—H7C | 110.00 |
C6—C1—C8 | 120.86 (17) | H7A—C7—H7B | 109.00 |
C2—C1—C6 | 117.49 (17) | H7A—C7—H7C | 110.00 |
C2—C1—C8 | 121.58 (16) | H7B—C7—H7C | 109.00 |
C1—C2—C3 | 121.33 (18) | C1—C8—H8 | 108.00 |
C2—C3—C4 | 120.4 (2) | C9—C8—H8 | 108.00 |
O1—C4—C3 | 115.55 (19) | C13—C8—H8 | 109.00 |
C3—C4—C5 | 119.50 (19) | C14—C15—H15A | 109.00 |
O1—C4—C5 | 124.96 (19) | C14—C15—H15B | 109.00 |
C4—C5—C6 | 119.47 (18) | C16—C15—H15A | 109.00 |
C1—C6—C5 | 121.83 (18) | C16—C15—H15B | 109.00 |
C1—C8—C13 | 112.40 (15) | H15A—C15—H15B | 108.00 |
C1—C8—C9 | 110.68 (14) | C12—C17—H17A | 109.00 |
C9—C8—C13 | 108.21 (14) | C12—C17—H17B | 109.00 |
C8—C9—C10 | 122.50 (16) | C16—C17—H17A | 109.00 |
C8—C9—C11 | 118.28 (15) | C16—C17—H17B | 109.00 |
C10—C9—C11 | 119.04 (16) | H17A—C17—H17B | 108.00 |
N2—C10—C9 | 128.41 (18) | C16—C18—H18A | 109.00 |
O2—C10—N2 | 110.29 (15) | C16—C18—H18B | 110.00 |
O2—C10—C9 | 121.30 (15) | C16—C18—H18C | 110.00 |
N1—C11—C9 | 179.09 (19) | H18A—C18—H18B | 109.00 |
O2—C12—C13 | 123.20 (16) | H18A—C18—H18C | 109.00 |
O2—C12—C17 | 110.77 (14) | H18B—C18—H18C | 109.00 |
C13—C12—C17 | 126.03 (16) | C16—C19—H19A | 109.00 |
C12—C13—C14 | 118.86 (16) | C16—C19—H19B | 109.00 |
C8—C13—C14 | 118.84 (15) | C16—C19—H19C | 109.00 |
C8—C13—C12 | 122.28 (15) | H19A—C19—H19B | 109.00 |
O3—C14—C13 | 121.03 (17) | H19A—C19—H19C | 109.00 |
O3—C14—C15 | 121.68 (16) | H19B—C19—H19C | 109.00 |
C13—C14—C15 | 117.26 (15) | O4—C20—C21 | 122.9 (4) |
C14—C15—C16 | 113.98 (16) | O4—C20—C22 | 122.7 (4) |
C17—C16—C18 | 108.51 (18) | C21—C20—C22 | 114.0 (3) |
C17—C16—C19 | 110.37 (18) | C20—C21—H21A | 109.00 |
C18—C16—C19 | 109.63 (19) | C20—C21—H21B | 109.00 |
C15—C16—C19 | 110.12 (19) | C20—C21—H21C | 109.00 |
C15—C16—C17 | 108.13 (17) | H21A—C21—H21B | 109.00 |
C15—C16—C18 | 110.05 (18) | H21A—C21—H21C | 109.00 |
C12—C17—C16 | 112.99 (15) | H21B—C21—H21C | 109.00 |
C1—C2—H2 | 119.00 | C20—C22—H22A | 109.00 |
C3—C2—H2 | 119.00 | C20—C22—H22B | 109.00 |
C2—C3—H3 | 120.00 | C20—C22—H22C | 109.00 |
C4—C3—H3 | 120.00 | H22A—C22—H22B | 109.00 |
C4—C5—H5 | 120.00 | H22A—C22—H22C | 110.00 |
C6—C5—H5 | 120.00 | H22B—C22—H22C | 109.00 |
C7—O1—C4—C3 | −180.0 (2) | C1—C8—C13—C14 | −74.3 (2) |
C7—O1—C4—C5 | 0.2 (3) | C9—C8—C13—C12 | −18.5 (2) |
C12—O2—C10—N2 | 172.48 (16) | C9—C8—C13—C14 | 163.20 (16) |
C12—O2—C10—C9 | −7.6 (3) | C8—C9—C10—O2 | −8.6 (3) |
C10—O2—C12—C13 | 9.5 (3) | C8—C9—C10—N2 | 171.34 (19) |
C10—O2—C12—C17 | −171.11 (16) | C11—C9—C10—O2 | 176.45 (17) |
C6—C1—C2—C3 | −0.2 (3) | C11—C9—C10—N2 | −3.6 (3) |
C8—C1—C2—C3 | −177.04 (18) | O2—C12—C13—C8 | 5.1 (3) |
C2—C1—C6—C5 | 0.2 (3) | O2—C12—C13—C14 | −176.54 (17) |
C8—C1—C6—C5 | 177.02 (16) | C17—C12—C13—C8 | −174.16 (18) |
C2—C1—C8—C9 | 79.6 (2) | C17—C12—C13—C14 | 4.2 (3) |
C2—C1—C8—C13 | −41.5 (2) | O2—C12—C17—C16 | −161.46 (16) |
C6—C1—C8—C9 | −97.08 (19) | C13—C12—C17—C16 | 17.9 (3) |
C6—C1—C8—C13 | 141.80 (17) | C8—C13—C14—O3 | 0.7 (3) |
C1—C2—C3—C4 | 0.2 (3) | C8—C13—C14—C15 | −177.12 (17) |
C2—C3—C4—O1 | −180.0 (2) | C12—C13—C14—O3 | −177.70 (19) |
C2—C3—C4—C5 | −0.1 (3) | C12—C13—C14—C15 | 4.5 (3) |
O1—C4—C5—C6 | 179.9 (2) | O3—C14—C15—C16 | 147.2 (2) |
C3—C4—C5—C6 | 0.1 (3) | C13—C14—C15—C16 | −35.0 (3) |
C4—C5—C6—C1 | −0.1 (3) | C14—C15—C16—C17 | 54.3 (2) |
C1—C8—C9—C10 | −103.3 (2) | C14—C15—C16—C18 | 172.66 (18) |
C1—C8—C9—C11 | 71.7 (2) | C14—C15—C16—C19 | −66.4 (2) |
C13—C8—C9—C10 | 20.3 (2) | C15—C16—C17—C12 | −45.0 (2) |
C13—C8—C9—C11 | −164.75 (16) | C18—C16—C17—C12 | −164.36 (18) |
C1—C8—C13—C12 | 104.1 (2) | C19—C16—C17—C12 | 75.5 (2) |
Cg2 is the centroid of the O2/C8–C10/C12/C13) 4H-pyran ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N1i | 0.86 | 2.30 | 3.142 (3) | 168 |
N2—H2B···O3ii | 0.86 | 2.19 | 3.029 (2) | 165 |
C6—H6···N1iii | 0.93 | 2.51 | 3.258 (3) | 137 |
C18—H18A···Cg2iv | 0.96 | 2.77 | 3.677 (2) | 158 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1; (iv) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C19H20N2O3·C3H6O |
Mr | 382.45 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 8.2037 (4), 9.5319 (4), 13.8390 (7) |
α, β, γ (°) | 77.743 (2), 87.307 (3), 80.672 (2) |
V (Å3) | 1043.43 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.28 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.978, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16752, 4917, 3284 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.660 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.182, 1.04 |
No. of reflections | 4917 |
No. of parameters | 246 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.59, −0.50 |
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).
Cg2 is the centroid of the O2/C8–C10/C12/C13) 4H-pyran ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N1i | 0.86 | 2.30 | 3.142 (3) | 168 |
N2—H2B···O3ii | 0.86 | 2.19 | 3.029 (2) | 165 |
C6—H6···N1iii | 0.93 | 2.51 | 3.258 (3) | 137 |
C18—H18A···Cg2iv | 0.96 | 2.77 | 3.677 (2) | 158 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+1; (iv) x, y−1, z. |
Acknowledgements
The financial support of the Egyptian Goverment to carry out this study is gratefully acknowledged. We also thank Manchester Metropolitan University and Erciyes University for guidance and instrumental support of the study.
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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.
Compounds such as 4H-chromenes and fused 4H-chromenes are a great class of organic drugs due to their wide applications in chemo therapy. They exhibited anticancer activities (Kemnitzer et al., 2007, 2008; Abd-El-Aziz et al., 2004, 2007; Gourdeau et al., 2004; Sabry et al., 2011; Mahdavi et al., 2011) and have used in treatment of Alzheimer's disease and Schizophrenia disorder (Brühlmann et al., 2001). In this context and further to our on-going study in synthesis and biological investigation of 4H-chromene compounds (Mohamed et al. 2012), we report in this study the structure and synthesis of the title compound (I).
In the title compound (I) shown in Fig. 1, the C12–C17 cyclohexene and O2/C8—C10/C12/C13 4H-pyran rings are puckered with the puckering parameters (Cremer & Pople, 1975) of QT = 0.456 (2) ° A, θ = 54.6 (3) °, φ = 225.2 (3) °, and QT = 0.201 (2) Å, θ = 108.1 (5) °, φ = 354.7 (6) °, respectively. The bond lengths and bond angles in (I) are normal and are comparable with those of a related structure previously reported (Mohamed et al., 2012).
In the crystal structure, adjacent molecules are connected 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 further connected to chains running along the a axis by N—H···O hydrogen bonds. Furthermore, C—H···π interactions contribute to the stabilization of the crystal packing (Table 1, Fig. 2).