organic compounds
4-(4-Methylphenyl)-2-(prop-2-yn-1-yl)phthalazin-1(2H)-one
aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
*Correspondence e-mail: dr@physics.uni-mysore.ac.in
In the title compound, C18H14N2O, the dihedral angle between the methylphenyl ring and the phthalazone ring system (r.m.s. deviation = 0.034 Å) is 53.93 (9)°. In the crystal, molecules are connected by C—H⋯O hydrogen bonds, forming chains along [101]. The chains are linked by π–π interactions [centroid–centroid distance 3.6990 (12) Å], forming layers parallel to (10-1).
CCDC reference: 979061
Related literature
For general background and the biological and pharmacological properties of phthalazine derivatives, see: Abd alla et al. (2010); Awadallah et al. (2012); Khalil et al. (2009); Kim et al. (2008); Ryu et al. (2007). For a related structure, see: Bausch et al. (1997).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2013); cell SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
CCDC reference: 979061
10.1107/S1600536813034880/is5329sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813034880/is5329Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813034880/is5329Isup3.cml
2-(4-Methylbenzoyl)benzoic acid (0.1 mol) is esterified in ethanol (25 ml) in presence of few drops of sulfuric acid. The ethyl 2-(4-methylbenzoyl)benzoate obtained is further refluxed with hydrazine hydrate (5 ml, 98%) in absolute ethanol (50 ml)for 2 hrs. Solid obtained on cooling was filtered off and dried to give 4-(4-methylphenyl)phthalazin-1-ol. A mixture of 4-(4-methylphenyl)phthalazin-1-ol (0.015 mol), anhydrous potassium carbonate (3.04 g, 0.022 mol) and propargylbromide (1.78 g, 0.015 mol) in DMF (25 ml) was stirred at 65 °C for 2 h. After completion of reaction, reaction mixture was poured into ice-cold water. The solid product obtained was purified by
using n-hexane and ethyl acetate as to get pure compound. Further the compound was recrystallized from ethyl acetate to get the yellow crystals (m.p. 168–170 °C).The H atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).
Nitrogen
have received a great attention because of their wide applicability in different areas, especially drugs (Kim et al., 2008). Phthalazines are an important class of nitrogen that possess exciting pharmacological and biological properties (Khalil et al., 2009). Phthalazines have been reported to possess antifungal (Ryu et al., 2007), antibacterial (Khalil et al., 2009), cytotoxic (Kim et al., 2008), anti-inflammatory (Abd alla et al., 2010), antihypertensive and vasorelaxant (Awadallah et al., 2012) properties. As part of our studies in this area, herewith we report the structure of the title compound.The ORTEP of the title compound is shown (Fig. 1). The phthalazine ring is nearly planar. The dihedral angle between the methylphenyl ring and the phenyl ring of the phthalazinone moiety is 53.93 (9)°. The bond lengths and bond angles of the title compound are comparable to related structure, 4-(9-fluorenoxy)-2-phenylphthalazin-1(2H)-one (Bausch et al., 1997). In the π–π are observed [minimum centroid-centroid distance 3.6990 (12) Å].
molecules are connected by intermolecular C—H···O hydrogen bonds (Fig. 2). Also, short contacts of the typeFor general background and the biological and pharmacological properties of phthalazine derivatives, see: Abd alla et al. (2010); Awadallah et al. (2012); Khalil et al. (2009); Kim et al. (2008); Ryu et al. (2007). For a related structure, see: Bausch et al. (1997).
Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).Fig. 1. ORTEP diagram of the title compound with 50% probability ellipsoids. | |
Fig. 2. Packing diagram of the title compound, viewed along the c axis. |
C18H14N2O | F(000) = 576 |
Mr = 274.31 | Dx = 1.266 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2yn | Cell parameters from 2337 reflections |
a = 11.9917 (19) Å | θ = 4.7–64.6° |
b = 9.7116 (16) Å | µ = 0.63 mm−1 |
c = 12.602 (2) Å | T = 296 K |
β = 101.285 (7)° | Block, yellow |
V = 1439.2 (4) Å3 | 0.23 × 0.20 × 0.19 mm |
Z = 4 |
Bruker X8 Proteum diffractometer | 2337 independent reflections |
Radiation source: Bruker MicroStar microfocus rotating anode | 2093 reflections with I > 2σ(I) |
Helios multilayer optics monochromator | Rint = 0.036 |
Detector resolution: 10.7 pixels mm-1 | θmax = 64.6°, θmin = 4.7° |
φ and ω scans | h = −13→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −10→11 |
Tmin = 0.864, Tmax = 0.886 | l = −8→14 |
8733 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0698P)2 + 0.2752P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.003 |
2337 reflections | Δρmax = 0.15 e Å−3 |
192 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXL, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0090 (9) |
C18H14N2O | V = 1439.2 (4) Å3 |
Mr = 274.31 | Z = 4 |
Monoclinic, P21/n | Cu Kα radiation |
a = 11.9917 (19) Å | µ = 0.63 mm−1 |
b = 9.7116 (16) Å | T = 296 K |
c = 12.602 (2) Å | 0.23 × 0.20 × 0.19 mm |
β = 101.285 (7)° |
Bruker X8 Proteum diffractometer | 2337 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | 2093 reflections with I > 2σ(I) |
Tmin = 0.864, Tmax = 0.886 | Rint = 0.036 |
8733 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.15 e Å−3 |
2337 reflections | Δρmin = −0.15 e Å−3 |
192 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 | 0.19809 (12) | −0.11059 (16) | 1.21105 (8) | 0.0755 (5) | |
N1 | 0.22126 (12) | 0.03101 (14) | 0.95663 (10) | 0.0524 (4) | |
N2 | 0.23069 (12) | 0.00807 (15) | 1.06549 (10) | 0.0548 (5) | |
C1 | 0.07580 (12) | −0.14488 (16) | 0.92636 (11) | 0.0464 (5) | |
C2 | 0.09215 (13) | −0.17108 (17) | 1.03779 (11) | 0.0486 (5) | |
C3 | 0.17640 (14) | −0.09248 (18) | 1.11276 (12) | 0.0536 (5) | |
C4 | 0.14781 (13) | −0.04216 (16) | 0.88990 (11) | 0.0468 (5) | |
C5 | −0.01049 (14) | −0.21765 (18) | 0.85760 (13) | 0.0562 (5) | |
C6 | −0.07462 (15) | −0.3140 (2) | 0.89874 (15) | 0.0645 (6) | |
C7 | −0.05524 (16) | −0.3416 (2) | 1.00855 (15) | 0.0647 (6) | |
C8 | 0.02715 (15) | −0.27061 (19) | 1.07770 (14) | 0.0588 (6) | |
C9 | 0.31525 (16) | 0.0952 (2) | 1.13355 (14) | 0.0646 (6) | |
C10 | 0.43037 (18) | 0.0402 (2) | 1.14605 (14) | 0.0653 (7) | |
C11 | 0.5226 (2) | −0.0013 (3) | 1.1548 (2) | 0.0997 (10) | |
C12 | 0.14520 (13) | −0.01379 (17) | 0.77355 (12) | 0.0473 (5) | |
C13 | 0.13700 (15) | 0.11933 (18) | 0.73343 (13) | 0.0554 (6) | |
C14 | 0.13974 (16) | 0.1456 (2) | 0.62603 (13) | 0.0604 (6) | |
C15 | 0.15141 (14) | 0.0409 (2) | 0.55518 (12) | 0.0567 (6) | |
C16 | 0.15944 (16) | −0.0918 (2) | 0.59542 (13) | 0.0638 (6) | |
C17 | 0.15584 (16) | −0.11952 (19) | 0.70219 (13) | 0.0583 (6) | |
C18 | 0.15649 (17) | 0.0690 (2) | 0.43701 (13) | 0.0708 (7) | |
H5 | −0.02440 | −0.20060 | 0.78360 | 0.0670* | |
H6 | −0.13170 | −0.36110 | 0.85220 | 0.0770* | |
H7 | −0.09810 | −0.40830 | 1.03530 | 0.0780* | |
H8 | 0.03990 | −0.28870 | 1.15150 | 0.0710* | |
H9A | 0.31310 | 0.18630 | 1.10180 | 0.0770* | |
H9B | 0.29570 | 0.10410 | 1.20440 | 0.0770* | |
H11 | 0.59650 | −0.03440 | 1.16180 | 0.1200* | |
H13 | 0.12950 | 0.19220 | 0.77940 | 0.0660* | |
H14 | 0.13360 | 0.23590 | 0.60110 | 0.0720* | |
H16 | 0.16750 | −0.16440 | 0.54940 | 0.0760* | |
H17 | 0.16060 | −0.21010 | 0.72650 | 0.0700* | |
H18A | 0.12210 | 0.15650 | 0.41580 | 0.1060* | |
H18B | 0.11620 | −0.00210 | 0.39220 | 0.1060* | |
H18C | 0.23440 | 0.07020 | 0.42870 | 0.1060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0829 (9) | 0.1064 (11) | 0.0305 (6) | −0.0022 (8) | −0.0054 (6) | 0.0047 (6) |
N1 | 0.0592 (8) | 0.0597 (8) | 0.0341 (7) | 0.0033 (6) | −0.0011 (6) | −0.0022 (6) |
N2 | 0.0602 (8) | 0.0656 (9) | 0.0324 (7) | 0.0008 (7) | −0.0062 (6) | −0.0062 (6) |
C1 | 0.0452 (8) | 0.0546 (9) | 0.0356 (8) | 0.0106 (7) | −0.0011 (6) | −0.0001 (6) |
C2 | 0.0463 (8) | 0.0616 (10) | 0.0347 (8) | 0.0120 (7) | 0.0004 (6) | 0.0012 (7) |
C3 | 0.0546 (9) | 0.0684 (11) | 0.0338 (8) | 0.0099 (8) | −0.0010 (7) | −0.0002 (7) |
C4 | 0.0485 (8) | 0.0534 (9) | 0.0340 (8) | 0.0077 (7) | −0.0029 (6) | −0.0022 (6) |
C5 | 0.0558 (9) | 0.0676 (11) | 0.0398 (8) | 0.0020 (8) | −0.0041 (7) | −0.0023 (7) |
C6 | 0.0544 (10) | 0.0732 (12) | 0.0611 (11) | −0.0037 (9) | −0.0001 (8) | −0.0053 (9) |
C7 | 0.0560 (10) | 0.0724 (12) | 0.0646 (11) | −0.0008 (9) | 0.0089 (8) | 0.0059 (9) |
C8 | 0.0555 (9) | 0.0757 (12) | 0.0446 (9) | 0.0087 (8) | 0.0084 (7) | 0.0102 (8) |
C9 | 0.0735 (12) | 0.0688 (12) | 0.0429 (9) | −0.0040 (9) | −0.0094 (8) | −0.0117 (8) |
C10 | 0.0669 (12) | 0.0716 (12) | 0.0519 (10) | −0.0129 (9) | −0.0015 (8) | −0.0003 (8) |
C11 | 0.0672 (15) | 0.0930 (17) | 0.135 (2) | −0.0067 (13) | 0.0102 (14) | 0.0109 (15) |
C12 | 0.0463 (8) | 0.0578 (9) | 0.0338 (8) | 0.0043 (7) | −0.0016 (6) | −0.0019 (6) |
C13 | 0.0683 (10) | 0.0552 (10) | 0.0416 (9) | −0.0007 (8) | 0.0081 (7) | −0.0051 (7) |
C14 | 0.0725 (11) | 0.0613 (10) | 0.0462 (9) | −0.0006 (8) | 0.0089 (8) | 0.0060 (8) |
C15 | 0.0498 (9) | 0.0820 (12) | 0.0360 (8) | −0.0015 (8) | 0.0027 (7) | −0.0015 (8) |
C16 | 0.0757 (12) | 0.0726 (12) | 0.0424 (9) | 0.0067 (9) | 0.0102 (8) | −0.0125 (8) |
C17 | 0.0726 (11) | 0.0572 (10) | 0.0434 (9) | 0.0116 (8) | 0.0075 (8) | −0.0021 (7) |
C18 | 0.0664 (11) | 0.1084 (16) | 0.0362 (9) | −0.0050 (11) | 0.0064 (8) | 0.0095 (9) |
O1—C3 | 1.2275 (18) | C14—C15 | 1.378 (3) |
N1—N2 | 1.3725 (18) | C15—C16 | 1.381 (3) |
N1—C4 | 1.303 (2) | C15—C18 | 1.527 (2) |
N2—C3 | 1.373 (2) | C16—C17 | 1.381 (2) |
N2—C9 | 1.463 (2) | C5—H5 | 0.9300 |
C1—C2 | 1.4026 (19) | C6—H6 | 0.9300 |
C1—C4 | 1.452 (2) | C7—H7 | 0.9300 |
C1—C5 | 1.404 (2) | C8—H8 | 0.9300 |
C2—C3 | 1.457 (2) | C9—H9A | 0.9700 |
C2—C8 | 1.396 (2) | C9—H9B | 0.9700 |
C4—C12 | 1.486 (2) | C11—H11 | 0.9300 |
C5—C6 | 1.375 (3) | C13—H13 | 0.9300 |
C6—C7 | 1.384 (3) | C14—H14 | 0.9300 |
C7—C8 | 1.369 (3) | C16—H16 | 0.9300 |
C9—C10 | 1.460 (3) | C17—H17 | 0.9300 |
C10—C11 | 1.162 (3) | C18—H18A | 0.9600 |
C12—C13 | 1.385 (2) | C18—H18B | 0.9600 |
C12—C17 | 1.387 (2) | C18—H18C | 0.9600 |
C13—C14 | 1.384 (2) | ||
N2—N1—C4 | 118.01 (13) | C15—C16—C17 | 121.75 (17) |
N1—N2—C3 | 126.58 (13) | C12—C17—C16 | 120.78 (17) |
N1—N2—C9 | 113.85 (13) | C1—C5—H5 | 120.00 |
C3—N2—C9 | 119.36 (13) | C6—C5—H5 | 120.00 |
C2—C1—C4 | 117.79 (13) | C5—C6—H6 | 120.00 |
C2—C1—C5 | 117.93 (14) | C7—C6—H6 | 120.00 |
C4—C1—C5 | 124.26 (13) | C6—C7—H7 | 120.00 |
C1—C2—C3 | 119.84 (14) | C8—C7—H7 | 120.00 |
C1—C2—C8 | 120.52 (14) | C2—C8—H8 | 120.00 |
C3—C2—C8 | 119.64 (13) | C7—C8—H8 | 120.00 |
O1—C3—N2 | 121.00 (16) | N2—C9—H9A | 109.00 |
O1—C3—C2 | 124.23 (16) | N2—C9—H9B | 109.00 |
N2—C3—C2 | 114.77 (13) | C10—C9—H9A | 109.00 |
N1—C4—C1 | 122.64 (13) | C10—C9—H9B | 109.00 |
N1—C4—C12 | 114.62 (14) | H9A—C9—H9B | 108.00 |
C1—C4—C12 | 122.73 (13) | C10—C11—H11 | 180.00 |
C1—C5—C6 | 120.59 (15) | C12—C13—H13 | 119.00 |
C5—C6—C7 | 120.79 (17) | C14—C13—H13 | 120.00 |
C6—C7—C8 | 119.87 (18) | C13—C14—H14 | 119.00 |
C2—C8—C7 | 120.25 (16) | C15—C14—H14 | 119.00 |
N2—C9—C10 | 112.59 (16) | C15—C16—H16 | 119.00 |
C9—C10—C11 | 178.6 (2) | C17—C16—H16 | 119.00 |
C4—C12—C13 | 121.31 (14) | C12—C17—H17 | 120.00 |
C4—C12—C17 | 121.03 (15) | C16—C17—H17 | 120.00 |
C13—C12—C17 | 117.61 (14) | C15—C18—H18A | 109.00 |
C12—C13—C14 | 121.04 (16) | C15—C18—H18B | 109.00 |
C13—C14—C15 | 121.49 (17) | C15—C18—H18C | 110.00 |
C14—C15—C16 | 117.33 (15) | H18A—C18—H18B | 109.00 |
C14—C15—C18 | 121.90 (17) | H18A—C18—H18C | 109.00 |
C16—C15—C18 | 120.77 (16) | H18B—C18—H18C | 109.00 |
C4—N1—N2—C3 | 5.4 (2) | C8—C2—C3—O1 | 2.6 (3) |
C4—N1—N2—C9 | −179.97 (16) | C8—C2—C3—N2 | −176.34 (16) |
N2—N1—C4—C1 | 0.6 (2) | C1—C2—C8—C7 | −1.5 (3) |
N2—N1—C4—C12 | −178.36 (14) | C3—C2—C8—C7 | 177.55 (17) |
N1—N2—C3—O1 | 174.12 (16) | N1—C4—C12—C13 | −50.0 (2) |
N1—N2—C3—C2 | −6.9 (2) | N1—C4—C12—C17 | 127.20 (17) |
C9—N2—C3—O1 | −0.3 (3) | C1—C4—C12—C13 | 131.06 (17) |
C9—N2—C3—C2 | 178.71 (15) | C1—C4—C12—C17 | −51.7 (2) |
N1—N2—C9—C10 | −83.42 (18) | C1—C5—C6—C7 | −0.2 (3) |
C3—N2—C9—C10 | 91.67 (19) | C5—C6—C7—C8 | 1.3 (3) |
C4—C1—C2—C3 | 2.2 (2) | C6—C7—C8—C2 | −0.4 (3) |
C4—C1—C2—C8 | −178.72 (15) | C4—C12—C13—C14 | 177.07 (16) |
C5—C1—C2—C3 | −176.58 (15) | C17—C12—C13—C14 | −0.2 (3) |
C5—C1—C2—C8 | 2.5 (2) | C4—C12—C17—C16 | −176.53 (17) |
C2—C1—C4—N1 | −4.1 (2) | C13—C12—C17—C16 | 0.8 (3) |
C2—C1—C4—C12 | 174.76 (15) | C12—C13—C14—C15 | −0.4 (3) |
C5—C1—C4—N1 | 174.61 (16) | C13—C14—C15—C16 | 0.5 (3) |
C5—C1—C4—C12 | −6.5 (2) | C13—C14—C15—C18 | −178.98 (17) |
C2—C1—C5—C6 | −1.6 (2) | C14—C15—C16—C17 | 0.1 (3) |
C4—C1—C5—C6 | 179.67 (16) | C18—C15—C16—C17 | 179.55 (18) |
C1—C2—C3—O1 | −178.30 (17) | C15—C16—C17—C12 | −0.7 (3) |
C1—C2—C3—N2 | 2.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1i | 0.93 | 2.45 | 3.322 (2) | 157 |
Symmetry code: (i) x−1/2, −y−1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1i | 0.93 | 2.45 | 3.322 (2) | 157 |
Symmetry code: (i) x−1/2, −y−1/2, z−1/2. |
Acknowledgements
The authors are grateful to the IOE, University of Mysore, for providing the single-crystal X-ray diffraction facility. MKU is grateful to the DST, New Delhi, for the award of an INSPIRE Fellowship. DR acknowledges the UGC, New Delhi, for financial support under the Major Research Project Scheme [No. F.41–882/2012 (SR)].
References
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Nitrogen heterocyclic compounds have received a great attention because of their wide applicability in different areas, especially drugs (Kim et al., 2008). Phthalazines are an important class of nitrogen heterocyclic compounds that possess exciting pharmacological and biological properties (Khalil et al., 2009). Phthalazines have been reported to possess antifungal (Ryu et al., 2007), antibacterial (Khalil et al., 2009), cytotoxic (Kim et al., 2008), anti-inflammatory (Abd alla et al., 2010), antihypertensive and vasorelaxant (Awadallah et al., 2012) properties. As part of our studies in this area, herewith we report the structure of the title compound.
The ORTEP of the title compound is shown (Fig. 1). The phthalazine ring is nearly planar. The dihedral angle between the methylphenyl ring and the phenyl ring of the phthalazinone moiety is 53.93 (9)°. The bond lengths and bond angles of the title compound are comparable to related structure, 4-(9-fluorenoxy)-2-phenylphthalazin-1(2H)-one (Bausch et al., 1997). In the crystal structure, molecules are connected by intermolecular C—H···O hydrogen bonds (Fig. 2). Also, short contacts of the type π–π are observed [minimum centroid-centroid distance 3.6990 (12) Å].