organic compounds
H-benzo[f]chromene-2-carbonitrile
of 3-amino-1-(4-hydroxyphenyl)-1aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bSchool of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, England, cChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, dChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, eChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
In the title compound, C20H14N2O2, the hydroxybenzene ring is almost perpendicular to the mean plane of the naphthalene ring system, making a dihedral angle of 85.56 (4)°. The 4H-pyran ring fused with the naphthalene ring system has a flattened boat conformation. In the crystal, O—H⋯N and N—H⋯O hydrogen bonds link the molecules into a supramolecular layer in the bc plane; N—H⋯π interactions also contribute to this arrangement. The layers are linked by weak by C—H⋯π and π–π [inter-centroid separation = 3.8713 (7) Å] interactions.
CCDC reference: 1409621
1. Related literature
For the biological activity of some heterocyclic derivatives containing the 4H-pyran unit, see: Elnagdi et al. (1983); Goldmann & Stoltefus (1991); Perez-Perez et al. (1995); Fan et al. (2010); Aytemir et al. (2004); Uher et al. (1994). For similar structures, see: Akkurt et al. (2013, 2015).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: CrystalClear-SM Expert (Rigaku, 2012); cell CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
CCDC reference: 1409621
https://doi.org/10.1107/S2056989015012566/tk5372sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015012566/tk5372Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015012566/tk5372Isup3.cml
The title compound was obtained in 95% yield from the reaction of 2-naphthol (144 mg; 1 mmol) and an equimolar amount of 4-hydroxybenzylidene-malononitrile (180 mg; 1 mmol) in absolute ethanol (10 ml ) in the presence of a catalytic amount of piperidine under reflux for 3 h. Crystallization of the crude product from ethanol gave colourless crystals of the title compound suitable for X-ray crystallography·M.pt: 521 K.
The H atoms of the OH and NH2 group were located in a difference Fourier map and were refined freely [N1—H1N = 0.896 (12) Å, N1—H2N = 0.883 (12) Å and O2—H2O = 0.885 (13) Å]. The H atoms attached to the C atoms were positioned geometrically, with C—H = 0.95 Å and C—H = 1.00 Å for aromatic and methine H, respectively, and with Uiso(H) = 1.2Ueq(C).
During the last decade, 4H-pyrans have held a unique role in medicinal chemistry due to their biological and pharmacological activities (Elnagdi et al., 1983; Goldmann & Stoltefus, 1991). Fused pyran derivatives also exhibit a wide spectrum of biological and pharmacological properties, such as antiviral and antileishmanial (Perez-Perez et al., 1995; Fan et al., 2010), anticonvulsant and antimicrobial (Aytemir et al., 2004) and insecticidal (Uher et al., 1994). In this context we report in this study the synthesis and crystal structural determination for the title compound.
In the title compound (Fig. 1), the hydroxy-benzene ring (C15–C20) is approximately perpendicular to the naphthalene ring system [C4–C13, maximum deviation = -0.017 (1) Å at atom C13] as indicated by the dihedral angle of 85.56 (4)°. The 4H-pyran ring (O1/C1–C4/C13) in the title compound is puckered with the puckering parameters of QT = 0.199 (1) Å, θ = 102.9 (3) ° and φ = 354.2 (3) °. The bond lengths and angles in the title compound are within normal ranges and comparable with those reported for the similar structures (Akkurt et al., 2013; 2015).
In the
molecules are linked by N—H···O and O—H···N hydrogen bonds (Table 1, Fig. 2), which leads to a layer in the bc plane.For general biological activities of some heterocyclic derivatives containing the 4H-pyran moiety, see: Elnagdi et al. (1983); Goldmann & Stoltefus (1991); Perez-Perez et al. (1995); Fan et al. (2010); Aytemir et al. (2004); Uher et al. (1994). For similar structures, see: Akkurt et al. (2013, 2015).
Data collection: CrystalClear-SM Expert (Rigaku, 2012); cell
CrystalClear-SM Expert (Rigaku, 2012); data reduction: CrystalClear-SM Expert (Rigaku, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).Fig. 1. View of the title compound with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. | |
Fig. 2. View of the packing of the title compound viewing down a axis. |
C20H14N2O2 | F(000) = 656 |
Mr = 314.33 | Dx = 1.302 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
a = 12.1086 (8) Å | Cell parameters from 17749 reflections |
b = 13.1418 (9) Å | θ = 2.3–27.5° |
c = 10.1552 (7) Å | µ = 0.09 mm−1 |
β = 96.992 (1)° | T = 100 K |
V = 1603.97 (19) Å3 | Blade, colourless |
Z = 4 | 0.21 × 0.08 × 0.07 mm |
Rigaku AFC12 (Right) diffractometer | 3679 independent reflections |
Radiation source: Rotating Anode | 3251 reflections with I > 2σ(I) |
Detector resolution: 28.5714 pixels mm-1 | Rint = 0.030 |
profile data from ω–scans | θmax = 27.5°, θmin = 2.9° |
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012) | h = −15→15 |
Tmin = 0.738, Tmax = 1.000 | k = −17→14 |
17411 measured reflections | l = −12→13 |
Refinement on F2 | 3 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.092 | w = 1/[σ2(Fo2) + (0.0425P)2 + 0.4007P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
3679 reflections | Δρmax = 0.26 e Å−3 |
229 parameters | Δρmin = −0.18 e Å−3 |
C20H14N2O2 | V = 1603.97 (19) Å3 |
Mr = 314.33 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.1086 (8) Å | µ = 0.09 mm−1 |
b = 13.1418 (9) Å | T = 100 K |
c = 10.1552 (7) Å | 0.21 × 0.08 × 0.07 mm |
β = 96.992 (1)° |
Rigaku AFC12 (Right) diffractometer | 3679 independent reflections |
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012) | 3251 reflections with I > 2σ(I) |
Tmin = 0.738, Tmax = 1.000 | Rint = 0.030 |
17411 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 3 restraints |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.26 e Å−3 |
3679 reflections | Δρmin = −0.18 e Å−3 |
229 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.33983 (8) | 0.47639 (8) | 1.11802 (10) | 0.0237 (2) | |
C2 | 0.31777 (8) | 0.53512 (7) | 1.00751 (9) | 0.0225 (2) | |
C3 | 0.22804 (8) | 0.50920 (7) | 0.89492 (9) | 0.02158 (19) | |
H3 | 0.1865 | 0.5730 | 0.8672 | 0.026* | |
C4 | 0.14741 (8) | 0.43453 (7) | 0.94430 (10) | 0.0234 (2) | |
C5 | 0.04093 (8) | 0.41495 (8) | 0.87013 (10) | 0.0261 (2) | |
C6 | 0.00288 (9) | 0.46750 (8) | 0.75126 (11) | 0.0295 (2) | |
H6 | 0.0494 | 0.5170 | 0.7178 | 0.035* | |
C7 | −0.10048 (9) | 0.44795 (9) | 0.68361 (12) | 0.0356 (3) | |
H7 | −0.1250 | 0.4847 | 0.6049 | 0.043* | |
C8 | −0.17001 (9) | 0.37399 (10) | 0.73009 (13) | 0.0380 (3) | |
H8 | −0.2408 | 0.3603 | 0.6822 | 0.046* | |
C9 | −0.13586 (9) | 0.32188 (9) | 0.84389 (13) | 0.0363 (3) | |
H9 | −0.1836 | 0.2722 | 0.8747 | 0.044* | |
C10 | −0.03025 (9) | 0.34047 (8) | 0.91728 (11) | 0.0300 (2) | |
C11 | 0.00527 (9) | 0.28765 (9) | 1.03649 (12) | 0.0348 (3) | |
H11 | −0.0417 | 0.2374 | 1.0675 | 0.042* | |
C12 | 0.10573 (9) | 0.30770 (8) | 1.10727 (12) | 0.0325 (2) | |
H12 | 0.1287 | 0.2723 | 1.1875 | 0.039* | |
C13 | 0.17513 (8) | 0.38188 (8) | 1.05958 (10) | 0.0256 (2) | |
C14 | 0.38247 (9) | 0.62331 (8) | 0.99791 (10) | 0.0264 (2) | |
C15 | 0.27956 (8) | 0.46801 (7) | 0.77552 (9) | 0.02106 (19) | |
C16 | 0.32470 (8) | 0.37029 (7) | 0.77790 (10) | 0.0233 (2) | |
H16 | 0.3201 | 0.3280 | 0.8529 | 0.028* | |
C17 | 0.37626 (8) | 0.33360 (7) | 0.67264 (10) | 0.0237 (2) | |
H17 | 0.4067 | 0.2669 | 0.6758 | 0.028* | |
C18 | 0.38308 (8) | 0.39533 (8) | 0.56223 (9) | 0.0235 (2) | |
C19 | 0.33979 (9) | 0.49308 (8) | 0.55907 (10) | 0.0272 (2) | |
H19 | 0.3453 | 0.5357 | 0.4846 | 0.033* | |
C20 | 0.28830 (8) | 0.52852 (8) | 0.66516 (10) | 0.0255 (2) | |
H20 | 0.2585 | 0.5955 | 0.6622 | 0.031* | |
N1 | 0.42225 (8) | 0.48875 (8) | 1.21728 (9) | 0.0297 (2) | |
N2 | 0.43322 (9) | 0.69661 (8) | 0.99112 (10) | 0.0383 (2) | |
O1 | 0.27537 (6) | 0.39555 (6) | 1.14083 (7) | 0.02776 (17) | |
O2 | 0.43199 (7) | 0.36270 (6) | 0.45510 (7) | 0.02998 (18) | |
H1N | 0.4259 (12) | 0.4453 (10) | 1.2856 (13) | 0.042 (4)* | |
H2N | 0.4767 (11) | 0.5317 (10) | 1.2069 (14) | 0.041 (4)* | |
H2O | 0.4737 (13) | 0.3086 (11) | 0.4770 (16) | 0.057 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0230 (5) | 0.0260 (5) | 0.0232 (5) | 0.0009 (4) | 0.0073 (4) | −0.0010 (4) |
C2 | 0.0224 (5) | 0.0251 (5) | 0.0207 (4) | −0.0014 (4) | 0.0050 (3) | −0.0007 (4) |
C3 | 0.0210 (4) | 0.0223 (4) | 0.0217 (4) | 0.0009 (3) | 0.0037 (3) | 0.0003 (3) |
C4 | 0.0221 (5) | 0.0226 (5) | 0.0266 (5) | 0.0006 (4) | 0.0074 (4) | −0.0028 (4) |
C5 | 0.0226 (5) | 0.0257 (5) | 0.0312 (5) | 0.0012 (4) | 0.0080 (4) | −0.0073 (4) |
C6 | 0.0246 (5) | 0.0322 (5) | 0.0318 (5) | 0.0016 (4) | 0.0040 (4) | −0.0067 (4) |
C7 | 0.0281 (5) | 0.0410 (6) | 0.0370 (6) | 0.0051 (5) | 0.0009 (4) | −0.0108 (5) |
C8 | 0.0223 (5) | 0.0430 (7) | 0.0483 (7) | 0.0012 (5) | 0.0022 (5) | −0.0184 (5) |
C9 | 0.0251 (5) | 0.0330 (6) | 0.0529 (7) | −0.0045 (4) | 0.0130 (5) | −0.0159 (5) |
C10 | 0.0249 (5) | 0.0266 (5) | 0.0405 (6) | −0.0014 (4) | 0.0116 (4) | −0.0089 (4) |
C11 | 0.0317 (5) | 0.0279 (5) | 0.0477 (7) | −0.0057 (4) | 0.0164 (5) | −0.0007 (5) |
C12 | 0.0338 (6) | 0.0287 (5) | 0.0370 (6) | −0.0008 (4) | 0.0119 (5) | 0.0051 (4) |
C13 | 0.0237 (5) | 0.0250 (5) | 0.0293 (5) | 0.0004 (4) | 0.0075 (4) | −0.0004 (4) |
C14 | 0.0277 (5) | 0.0328 (5) | 0.0189 (4) | −0.0026 (4) | 0.0035 (4) | 0.0001 (4) |
C15 | 0.0190 (4) | 0.0237 (5) | 0.0204 (4) | −0.0002 (3) | 0.0020 (3) | −0.0005 (3) |
C16 | 0.0251 (5) | 0.0232 (5) | 0.0221 (4) | −0.0006 (4) | 0.0046 (4) | 0.0033 (4) |
C17 | 0.0251 (5) | 0.0206 (4) | 0.0258 (5) | 0.0017 (4) | 0.0045 (4) | 0.0009 (4) |
C18 | 0.0224 (4) | 0.0285 (5) | 0.0196 (4) | 0.0012 (4) | 0.0032 (3) | −0.0011 (4) |
C19 | 0.0308 (5) | 0.0294 (5) | 0.0215 (5) | 0.0051 (4) | 0.0045 (4) | 0.0067 (4) |
C20 | 0.0279 (5) | 0.0238 (5) | 0.0249 (5) | 0.0058 (4) | 0.0039 (4) | 0.0033 (4) |
N1 | 0.0284 (5) | 0.0386 (5) | 0.0218 (4) | −0.0026 (4) | 0.0020 (3) | 0.0042 (4) |
N2 | 0.0448 (6) | 0.0404 (6) | 0.0292 (5) | −0.0161 (5) | 0.0028 (4) | 0.0030 (4) |
O1 | 0.0269 (4) | 0.0280 (4) | 0.0285 (4) | −0.0009 (3) | 0.0036 (3) | 0.0063 (3) |
O2 | 0.0364 (4) | 0.0326 (4) | 0.0223 (4) | 0.0095 (3) | 0.0091 (3) | 0.0022 (3) |
C1—N1 | 1.3393 (13) | C11—C12 | 1.3612 (17) |
C1—O1 | 1.3548 (12) | C11—H11 | 0.9500 |
C1—C2 | 1.3614 (14) | C12—C13 | 1.4108 (14) |
C2—C14 | 1.4089 (14) | C12—H12 | 0.9500 |
C2—C3 | 1.5171 (13) | C13—O1 | 1.3937 (12) |
C3—C4 | 1.5122 (13) | C14—N2 | 1.1492 (14) |
C3—C15 | 1.5286 (13) | C15—C20 | 1.3887 (13) |
C3—H3 | 1.0000 | C15—C16 | 1.3948 (13) |
C4—C13 | 1.3661 (14) | C16—C17 | 1.3883 (13) |
C4—C5 | 1.4351 (14) | C16—H16 | 0.9500 |
C5—C6 | 1.4180 (15) | C17—C18 | 1.3945 (13) |
C5—C10 | 1.4250 (15) | C17—H17 | 0.9500 |
C6—C7 | 1.3765 (15) | C18—O2 | 1.3693 (11) |
C6—H6 | 0.9500 | C18—C19 | 1.3864 (14) |
C7—C8 | 1.4047 (18) | C19—C20 | 1.3892 (14) |
C7—H7 | 0.9500 | C19—H19 | 0.9500 |
C8—C9 | 1.3636 (19) | C20—H20 | 0.9500 |
C8—H8 | 0.9500 | N1—H1N | 0.896 (12) |
C9—C10 | 1.4207 (15) | N1—H2N | 0.883 (12) |
C9—H9 | 0.9500 | O2—H2O | 0.885 (13) |
C10—C11 | 1.4162 (17) | ||
N1—C1—O1 | 111.01 (9) | C12—C11—C10 | 121.03 (10) |
N1—C1—C2 | 127.23 (10) | C12—C11—H11 | 119.5 |
O1—C1—C2 | 121.75 (9) | C10—C11—H11 | 119.5 |
C1—C2—C14 | 117.94 (9) | C11—C12—C13 | 118.93 (10) |
C1—C2—C3 | 122.99 (9) | C11—C12—H12 | 120.5 |
C14—C2—C3 | 119.07 (8) | C13—C12—H12 | 120.5 |
C4—C3—C2 | 109.14 (8) | C4—C13—O1 | 123.20 (9) |
C4—C3—C15 | 112.06 (8) | C4—C13—C12 | 123.35 (10) |
C2—C3—C15 | 110.69 (8) | O1—C13—C12 | 113.46 (9) |
C4—C3—H3 | 108.3 | N2—C14—C2 | 178.35 (12) |
C2—C3—H3 | 108.3 | C20—C15—C16 | 118.23 (9) |
C15—C3—H3 | 108.3 | C20—C15—C3 | 121.06 (8) |
C13—C4—C5 | 118.06 (9) | C16—C15—C3 | 120.61 (8) |
C13—C4—C3 | 120.77 (9) | C17—C16—C15 | 121.23 (9) |
C5—C4—C3 | 121.16 (9) | C17—C16—H16 | 119.4 |
C6—C5—C10 | 118.25 (10) | C15—C16—H16 | 119.4 |
C6—C5—C4 | 122.52 (10) | C16—C17—C18 | 119.55 (9) |
C10—C5—C4 | 119.23 (10) | C16—C17—H17 | 120.2 |
C7—C6—C5 | 121.03 (11) | C18—C17—H17 | 120.2 |
C7—C6—H6 | 119.5 | O2—C18—C19 | 118.08 (9) |
C5—C6—H6 | 119.5 | O2—C18—C17 | 122.03 (9) |
C6—C7—C8 | 120.47 (12) | C19—C18—C17 | 119.90 (9) |
C6—C7—H7 | 119.8 | C18—C19—C20 | 119.79 (9) |
C8—C7—H7 | 119.8 | C18—C19—H19 | 120.1 |
C9—C8—C7 | 120.00 (11) | C20—C19—H19 | 120.1 |
C9—C8—H8 | 120.0 | C15—C20—C19 | 121.29 (9) |
C7—C8—H8 | 120.0 | C15—C20—H20 | 119.4 |
C8—C9—C10 | 121.26 (11) | C19—C20—H20 | 119.4 |
C8—C9—H9 | 119.4 | C1—N1—H1N | 117.9 (9) |
C10—C9—H9 | 119.4 | C1—N1—H2N | 119.1 (9) |
C11—C10—C9 | 121.63 (10) | H1N—N1—H2N | 122.1 (13) |
C11—C10—C5 | 119.39 (10) | C1—O1—C13 | 118.57 (8) |
C9—C10—C5 | 118.98 (11) | C18—O2—H2O | 109.9 (11) |
N1—C1—C2—C14 | −4.87 (16) | C9—C10—C11—C12 | −178.64 (10) |
O1—C1—C2—C14 | 173.97 (9) | C5—C10—C11—C12 | 0.69 (16) |
N1—C1—C2—C3 | 174.55 (9) | C10—C11—C12—C13 | −0.47 (17) |
O1—C1—C2—C3 | −6.61 (15) | C5—C4—C13—O1 | −179.02 (9) |
C1—C2—C3—C4 | 18.81 (13) | C3—C4—C13—O1 | 2.51 (15) |
C14—C2—C3—C4 | −161.78 (9) | C5—C4—C13—C12 | 1.68 (15) |
C1—C2—C3—C15 | −104.97 (10) | C3—C4—C13—C12 | −176.79 (9) |
C14—C2—C3—C15 | 74.44 (11) | C11—C12—C13—C4 | −0.76 (16) |
C2—C3—C4—C13 | −16.41 (12) | C11—C12—C13—O1 | 179.88 (9) |
C15—C3—C4—C13 | 106.56 (10) | C4—C3—C15—C20 | 134.98 (10) |
C2—C3—C4—C5 | 165.16 (8) | C2—C3—C15—C20 | −102.93 (10) |
C15—C3—C4—C5 | −71.87 (11) | C4—C3—C15—C16 | −48.65 (12) |
C13—C4—C5—C6 | 178.20 (9) | C2—C3—C15—C16 | 73.44 (11) |
C3—C4—C5—C6 | −3.33 (14) | C20—C15—C16—C17 | −0.56 (14) |
C13—C4—C5—C10 | −1.40 (14) | C3—C15—C16—C17 | −177.04 (9) |
C3—C4—C5—C10 | 177.07 (9) | C15—C16—C17—C18 | −0.08 (15) |
C10—C5—C6—C7 | 0.61 (15) | C16—C17—C18—O2 | −179.34 (9) |
C4—C5—C6—C7 | −178.99 (10) | C16—C17—C18—C19 | 0.85 (15) |
C5—C6—C7—C8 | −1.03 (16) | O2—C18—C19—C20 | 179.21 (9) |
C6—C7—C8—C9 | 0.84 (17) | C17—C18—C19—C20 | −0.97 (16) |
C7—C8—C9—C10 | −0.24 (17) | C16—C15—C20—C19 | 0.45 (15) |
C8—C9—C10—C11 | 179.16 (10) | C3—C15—C20—C19 | 176.91 (9) |
C8—C9—C10—C5 | −0.17 (16) | C18—C19—C20—C15 | 0.31 (16) |
C6—C5—C10—C11 | −179.35 (9) | N1—C1—O1—C13 | 169.17 (8) |
C4—C5—C10—C11 | 0.26 (14) | C2—C1—O1—C13 | −9.84 (14) |
C6—C5—C10—C9 | −0.01 (14) | C4—C13—O1—C1 | 12.00 (14) |
C4—C5—C10—C9 | 179.60 (9) | C12—C13—O1—C1 | −168.63 (9) |
Cg3 and Cg4 are the centroids of the C5–C10 and C15–C20 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.90 (1) | 2.03 (1) | 2.9191 (12) | 173 (1) |
O2—H2O···N2ii | 0.89 (1) | 1.86 (1) | 2.7403 (12) | 175 (2) |
N1—H2N···Cg4iii | 0.88 (1) | 2.55 (1) | 3.2340 (11) | 135 (1) |
C11—H11···Cg3iv | 0.95 | 2.97 | 3.7610 (13) | 142 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, −y+1, −z+2; (iv) x, −y−1/2, z−1/2. |
Cg3 and Cg4 are the centroids of the C5–C10 and C15–C20 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.896 (12) | 2.029 (12) | 2.9191 (12) | 172.7 (13) |
O2—H2O···N2ii | 0.885 (13) | 1.858 (14) | 2.7403 (12) | 174.9 (16) |
N1—H2N···Cg4iii | 0.883 (12) | 2.547 (14) | 3.2340 (11) | 135.2 (11) |
C11—H11···Cg3iv | 0.95 | 2.97 | 3.7610 (13) | 142 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, −y+1, −z+2; (iv) x, −y−1/2, z−1/2. |
Acknowledgements
The authors would like to express their thanks to National Crystallography Service (NCS), Southampton, UK, for providing the X-ray data.
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During the last decade, 4H-pyrans have held a unique role in medicinal chemistry due to their biological and pharmacological activities (Elnagdi et al., 1983; Goldmann & Stoltefus, 1991). Fused pyran derivatives also exhibit a wide spectrum of biological and pharmacological properties, such as antiviral and antileishmanial (Perez-Perez et al., 1995; Fan et al., 2010), anticonvulsant and antimicrobial (Aytemir et al., 2004) and insecticidal (Uher et al., 1994). In this context we report in this study the synthesis and crystal structural determination for the title compound.
In the title compound (Fig. 1), the hydroxy-benzene ring (C15–C20) is approximately perpendicular to the naphthalene ring system [C4–C13, maximum deviation = -0.017 (1) Å at atom C13] as indicated by the dihedral angle of 85.56 (4)°. The 4H-pyran ring (O1/C1–C4/C13) in the title compound is puckered with the puckering parameters of QT = 0.199 (1) Å, θ = 102.9 (3) ° and φ = 354.2 (3) °. The bond lengths and angles in the title compound are within normal ranges and comparable with those reported for the similar structures (Akkurt et al., 2013; 2015).
In the crystal structure, molecules are linked by N—H···O and O—H···N hydrogen bonds (Table 1, Fig. 2), which leads to a layer in the bc plane.