organic compounds
3-Acetyl-1,5-diphenyl-1H-pyrazole-4-carbonitrile
aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my
The title compound, C18H13N3O, has a butterfly-like structure, in which the pyrazole ring forms dihedral angles of 59.31 (8) and 57.24 (8)° with the two phenyl rings. The dihedral angle between the two phenyl rings is 64.03 (8)°. The pyrazole ring and the C—C=O plane of the acetyl group are twisted slightly, making a dihedral angle of 7.95 (18)°. In the crystal, molecules are linked through weak C—H⋯N and C—H⋯O interactions into a helical chain along the a-axis direction.
Related literature
For bond-length data, see: Allen et al. (1987). For background to and the bioactivity of pyrazole derivatives, see: Abdel-Aziz et al. (2009, 2010); Abdel-Wahab et al. (2009); Bharate et al. (2008); Dawood et al. (2003); Fu et al. (2010); Thumar & Patel (2011). For a related structure, see: Abdel-Aziz et al. (2011).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812010938/is5091sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812010938/is5091Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812010938/is5091Isup3.cml
The title compound was prepared according to the reported method (Dawood et al., 2003). Single crystals of the title compound suitable for X-ray
were recrystallized from ethanol by the slow evaporation of the solvent at room temperature after several days.All H atoms were placed in calculated positions with d(C—H) = 0.93 for aromatic and 0.96 Å for CH3 atoms. The Uiso(H) values were constrained to be 1.5Ueq of the
for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups.Owing to the various biological properties of pyrazole derivatives such as anti-cancer (Fu et al., 2010), anti-inflammatory (Bharate et al., 2008) and antimicrobial activities (Thumar & Patel, 2011), we have during the course of our medicinal chemistry research reported the synthesis and bioactivity of pyrazole derivatives (Abdel-Aziz et al., 2009, 2010; Abdel-Wahab et al., 2009). The title compound (I) was synthesized and characterized in order to study the structure activity relationship of this class of compounds.
The molecule of (I), C18H13N3O, has a butterfly-like structure. The pyrazole ring forms the dihedral angles of 59.31 (8) and 57.24 (8)°, respectively, with the C5–C10 and C11–C16 phenyl rings, whereas the dihedral angle between these two rings is 64.03 (8)°. The cabonitrile substituent lies on the same plane with the pyrazole ring with an r.m.s. 0.0027 (1) Å for the seven non-H atoms (C1–C4/N1–N3), whereas the acetyl group is slightly deviated with the torsion angles N2–C1–C17–C18 = 8.3 (2)° and N2–C1–C17–O1 = -171.47 (13)°. The bond distances in (I) are within normal ranges (Allen et al., 1987) and comparable to the related structure (Abdel-Aziz et al., 2011). The crystal packing of (I) is stabilized by weak C—H···N and C—H···O interactions (Table 1). Figure 2 shows the molecular a helical chain along the [1 0 0] linked by these interactions.
For bond-length data, see: Allen et al. (1987). For background to and the bioactivity of pyrazole derivatives, see: Abdel-Aziz et al. (2009, 2010); Abdel-Wahab et al. (2009); Bharate et al. (2008); Dawood et al. (2003); Fu et al. (2010); Thumar & Patel (2011). For a related structure, see: Abdel-Aziz et al. (2011).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).C18H13N3O | F(000) = 1200 |
Mr = 287.31 | Dx = 1.282 Mg m−3 |
Orthorhombic, Pbca | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2782 reflections |
a = 6.8322 (2) Å | θ = 3.4–69.9° |
b = 16.8974 (5) Å | µ = 0.66 mm−1 |
c = 25.7968 (6) Å | T = 296 K |
V = 2978.15 (14) Å3 | Block, colorless |
Z = 8 | 0.56 × 0.35 × 0.23 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 2782 independent reflections |
Radiation source: sealed tube | 2338 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 69.9°, θmin = 3.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −6→8 |
Tmin = 0.708, Tmax = 0.863 | k = −20→20 |
10678 measured reflections | l = −31→23 |
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)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0586P)2 + 0.4109P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
2782 reflections | Δρmax = 0.18 e Å−3 |
201 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0012 (2) |
C18H13N3O | V = 2978.15 (14) Å3 |
Mr = 287.31 | Z = 8 |
Orthorhombic, Pbca | Cu Kα radiation |
a = 6.8322 (2) Å | µ = 0.66 mm−1 |
b = 16.8974 (5) Å | T = 296 K |
c = 25.7968 (6) Å | 0.56 × 0.35 × 0.23 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 2782 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2338 reflections with I > 2σ(I) |
Tmin = 0.708, Tmax = 0.863 | Rint = 0.026 |
10678 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.18 e Å−3 |
2782 reflections | Δρmin = −0.17 e Å−3 |
201 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.04907 (16) | 0.77988 (6) | 0.34667 (4) | 0.0461 (3) | |
N2 | 0.03430 (17) | 0.83315 (7) | 0.30758 (4) | 0.0501 (3) | |
N3 | 0.1596 (2) | 0.59304 (10) | 0.21580 (6) | 0.0737 (4) | |
O1 | 0.05198 (19) | 0.78631 (8) | 0.17444 (4) | 0.0747 (4) | |
C1 | 0.06117 (18) | 0.79131 (8) | 0.26452 (5) | 0.0480 (3) | |
C2 | 0.09573 (19) | 0.71052 (8) | 0.27627 (5) | 0.0463 (3) | |
C3 | 0.08526 (18) | 0.70532 (8) | 0.32961 (5) | 0.0441 (3) | |
C4 | 0.1299 (2) | 0.64619 (10) | 0.24210 (5) | 0.0536 (4) | |
C5 | 0.0947 (2) | 0.63535 (8) | 0.36354 (5) | 0.0458 (3) | |
C6 | 0.2582 (2) | 0.58729 (10) | 0.36412 (6) | 0.0628 (4) | |
H6A | 0.3661 | 0.5995 | 0.3436 | 0.075* | |
C7 | 0.2603 (3) | 0.52048 (10) | 0.39553 (8) | 0.0783 (5) | |
H7A | 0.3702 | 0.4880 | 0.3961 | 0.094* | |
C8 | 0.1016 (4) | 0.50213 (10) | 0.42561 (7) | 0.0785 (6) | |
H8A | 0.1043 | 0.4575 | 0.4467 | 0.094* | |
C9 | −0.0597 (3) | 0.54911 (10) | 0.42477 (7) | 0.0741 (5) | |
H9A | −0.1675 | 0.5363 | 0.4451 | 0.089* | |
C10 | −0.0647 (2) | 0.61553 (9) | 0.39400 (6) | 0.0580 (4) | |
H10A | −0.1758 | 0.6473 | 0.3937 | 0.070* | |
C11 | 0.0388 (2) | 0.80605 (8) | 0.39950 (5) | 0.0466 (3) | |
C12 | 0.1957 (2) | 0.79135 (9) | 0.43180 (6) | 0.0566 (4) | |
H12A | 0.3064 | 0.7656 | 0.4194 | 0.068* | |
C13 | 0.1858 (3) | 0.81549 (10) | 0.48280 (6) | 0.0650 (4) | |
H13A | 0.2901 | 0.8055 | 0.5050 | 0.078* | |
C14 | 0.0225 (3) | 0.85426 (9) | 0.50097 (6) | 0.0658 (4) | |
H14A | 0.0164 | 0.8703 | 0.5354 | 0.079* | |
C15 | −0.1319 (3) | 0.86926 (10) | 0.46807 (6) | 0.0662 (4) | |
H15A | −0.2414 | 0.8961 | 0.4803 | 0.079* | |
C16 | −0.1254 (2) | 0.84480 (9) | 0.41697 (6) | 0.0576 (4) | |
H16A | −0.2302 | 0.8544 | 0.3948 | 0.069* | |
C17 | 0.0492 (2) | 0.82851 (10) | 0.21251 (5) | 0.0568 (4) | |
C18 | 0.0336 (3) | 0.91591 (11) | 0.20952 (7) | 0.0755 (5) | |
H18A | −0.0431 | 0.9303 | 0.1798 | 0.113* | |
H18C | 0.1621 | 0.9384 | 0.2065 | 0.113* | |
H18D | −0.0284 | 0.9356 | 0.2403 | 0.113* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0550 (6) | 0.0450 (6) | 0.0383 (5) | −0.0011 (5) | −0.0011 (4) | 0.0056 (4) |
N2 | 0.0541 (6) | 0.0525 (6) | 0.0438 (6) | −0.0019 (5) | −0.0021 (5) | 0.0112 (5) |
N3 | 0.0732 (9) | 0.0852 (10) | 0.0626 (8) | 0.0025 (8) | 0.0026 (7) | −0.0182 (8) |
O1 | 0.0859 (8) | 0.0965 (9) | 0.0417 (6) | −0.0136 (7) | −0.0014 (5) | 0.0109 (6) |
C1 | 0.0429 (6) | 0.0603 (8) | 0.0407 (7) | −0.0073 (6) | −0.0012 (5) | 0.0096 (6) |
C2 | 0.0429 (6) | 0.0566 (8) | 0.0395 (6) | −0.0071 (6) | 0.0003 (5) | 0.0014 (6) |
C3 | 0.0446 (6) | 0.0474 (7) | 0.0404 (6) | −0.0036 (5) | 0.0002 (5) | 0.0014 (5) |
C4 | 0.0479 (7) | 0.0701 (9) | 0.0429 (7) | −0.0050 (7) | 0.0009 (6) | −0.0026 (7) |
C5 | 0.0579 (7) | 0.0430 (7) | 0.0363 (6) | −0.0014 (6) | −0.0021 (5) | −0.0020 (5) |
C6 | 0.0642 (9) | 0.0621 (9) | 0.0622 (9) | 0.0079 (7) | −0.0024 (7) | −0.0025 (7) |
C7 | 0.0960 (13) | 0.0558 (9) | 0.0832 (12) | 0.0250 (9) | −0.0237 (11) | −0.0051 (9) |
C8 | 0.1315 (17) | 0.0486 (9) | 0.0554 (9) | 0.0027 (10) | −0.0064 (10) | 0.0067 (7) |
C9 | 0.1125 (14) | 0.0530 (9) | 0.0568 (9) | −0.0034 (9) | 0.0177 (9) | 0.0085 (7) |
C10 | 0.0738 (9) | 0.0493 (8) | 0.0508 (8) | 0.0007 (7) | 0.0113 (7) | 0.0040 (6) |
C11 | 0.0603 (7) | 0.0395 (6) | 0.0400 (6) | −0.0025 (6) | −0.0011 (6) | 0.0034 (5) |
C12 | 0.0651 (9) | 0.0520 (8) | 0.0526 (8) | 0.0055 (7) | −0.0077 (6) | −0.0043 (6) |
C13 | 0.0863 (11) | 0.0575 (9) | 0.0511 (8) | 0.0016 (8) | −0.0186 (8) | −0.0037 (7) |
C14 | 0.0962 (12) | 0.0568 (9) | 0.0445 (8) | −0.0048 (8) | −0.0002 (8) | −0.0051 (7) |
C15 | 0.0801 (10) | 0.0616 (9) | 0.0571 (9) | 0.0084 (8) | 0.0100 (8) | −0.0040 (7) |
C16 | 0.0650 (9) | 0.0580 (8) | 0.0499 (8) | 0.0069 (7) | −0.0005 (6) | 0.0038 (7) |
C17 | 0.0460 (7) | 0.0792 (10) | 0.0451 (8) | −0.0084 (7) | −0.0012 (6) | 0.0152 (7) |
C18 | 0.0816 (11) | 0.0821 (12) | 0.0627 (10) | 0.0030 (9) | 0.0005 (8) | 0.0291 (9) |
N1—N2 | 1.3555 (15) | C9—C10 | 1.375 (2) |
N1—C3 | 1.3572 (17) | C9—H9A | 0.9300 |
N1—C11 | 1.4346 (17) | C10—H10A | 0.9300 |
N2—C1 | 1.3294 (18) | C11—C16 | 1.375 (2) |
N3—C4 | 1.144 (2) | C11—C12 | 1.380 (2) |
O1—C17 | 1.214 (2) | C12—C13 | 1.379 (2) |
C1—C2 | 1.418 (2) | C12—H12A | 0.9300 |
C1—C17 | 1.4840 (18) | C13—C14 | 1.376 (3) |
C2—C3 | 1.3807 (18) | C13—H13A | 0.9300 |
C2—C4 | 1.419 (2) | C14—C15 | 1.378 (2) |
C3—C5 | 1.4724 (18) | C14—H14A | 0.9300 |
C5—C6 | 1.381 (2) | C15—C16 | 1.382 (2) |
C5—C10 | 1.384 (2) | C15—H15A | 0.9300 |
C6—C7 | 1.390 (2) | C16—H16A | 0.9300 |
C6—H6A | 0.9300 | C17—C18 | 1.483 (2) |
C7—C8 | 1.369 (3) | C18—H18A | 0.9600 |
C7—H7A | 0.9300 | C18—H18C | 0.9600 |
C8—C9 | 1.359 (3) | C18—H18D | 0.9600 |
C8—H8A | 0.9300 | ||
N2—N1—C3 | 112.88 (11) | C9—C10—H10A | 119.8 |
N2—N1—C11 | 119.90 (10) | C5—C10—H10A | 119.8 |
C3—N1—C11 | 127.08 (11) | C16—C11—C12 | 121.44 (13) |
C1—N2—N1 | 104.96 (11) | C16—C11—N1 | 119.87 (12) |
N2—C1—C2 | 110.88 (11) | C12—C11—N1 | 118.69 (12) |
N2—C1—C17 | 121.50 (13) | C13—C12—C11 | 118.99 (15) |
C2—C1—C17 | 127.60 (13) | C13—C12—H12A | 120.5 |
C3—C2—C1 | 105.40 (12) | C11—C12—H12A | 120.5 |
C3—C2—C4 | 125.39 (13) | C14—C13—C12 | 120.36 (15) |
C1—C2—C4 | 129.20 (13) | C14—C13—H13A | 119.8 |
N1—C3—C2 | 105.88 (11) | C12—C13—H13A | 119.8 |
N1—C3—C5 | 124.11 (11) | C13—C14—C15 | 119.91 (14) |
C2—C3—C5 | 129.87 (12) | C13—C14—H14A | 120.0 |
N3—C4—C2 | 177.90 (16) | C15—C14—H14A | 120.0 |
C6—C5—C10 | 119.21 (14) | C14—C15—C16 | 120.54 (15) |
C6—C5—C3 | 120.93 (13) | C14—C15—H15A | 119.7 |
C10—C5—C3 | 119.83 (12) | C16—C15—H15A | 119.7 |
C5—C6—C7 | 119.48 (16) | C11—C16—C15 | 118.75 (15) |
C5—C6—H6A | 120.3 | C11—C16—H16A | 120.6 |
C7—C6—H6A | 120.3 | C15—C16—H16A | 120.6 |
C8—C7—C6 | 120.43 (17) | O1—C17—C18 | 122.97 (14) |
C8—C7—H7A | 119.8 | O1—C17—C1 | 118.81 (15) |
C6—C7—H7A | 119.8 | C18—C17—C1 | 118.22 (14) |
C9—C8—C7 | 120.07 (16) | C17—C18—H18A | 109.5 |
C9—C8—H8A | 120.0 | C17—C18—H18C | 109.5 |
C7—C8—H8A | 120.0 | H18A—C18—H18C | 109.5 |
C8—C9—C10 | 120.41 (18) | C17—C18—H18D | 109.5 |
C8—C9—H9A | 119.8 | H18A—C18—H18D | 109.5 |
C10—C9—H9A | 119.8 | H18C—C18—H18D | 109.5 |
C9—C10—C5 | 120.39 (16) | ||
C3—N1—N2—C1 | 0.20 (14) | C5—C6—C7—C8 | 0.2 (3) |
C11—N1—N2—C1 | 176.31 (11) | C6—C7—C8—C9 | 0.3 (3) |
N1—N2—C1—C2 | −0.67 (14) | C7—C8—C9—C10 | −0.4 (3) |
N1—N2—C1—C17 | 177.93 (11) | C8—C9—C10—C5 | 0.0 (3) |
N2—C1—C2—C3 | 0.89 (15) | C6—C5—C10—C9 | 0.5 (2) |
C17—C1—C2—C3 | −177.61 (12) | C3—C5—C10—C9 | 178.21 (14) |
N2—C1—C2—C4 | 179.54 (13) | N2—N1—C11—C16 | 59.51 (17) |
C17—C1—C2—C4 | 1.0 (2) | C3—N1—C11—C16 | −124.99 (15) |
N2—N1—C3—C2 | 0.34 (14) | N2—N1—C11—C12 | −120.59 (14) |
C11—N1—C3—C2 | −175.42 (12) | C3—N1—C11—C12 | 54.91 (19) |
N2—N1—C3—C5 | −175.66 (11) | C16—C11—C12—C13 | 0.7 (2) |
C11—N1—C3—C5 | 8.6 (2) | N1—C11—C12—C13 | −179.21 (13) |
C1—C2—C3—N1 | −0.71 (14) | C11—C12—C13—C14 | −0.6 (2) |
C4—C2—C3—N1 | −179.43 (12) | C12—C13—C14—C15 | −0.1 (3) |
C1—C2—C3—C5 | 174.97 (13) | C13—C14—C15—C16 | 0.8 (3) |
C4—C2—C3—C5 | −3.7 (2) | C12—C11—C16—C15 | 0.0 (2) |
N1—C3—C5—C6 | −124.42 (15) | N1—C11—C16—C15 | 179.86 (14) |
C2—C3—C5—C6 | 60.6 (2) | C14—C15—C16—C11 | −0.7 (3) |
N1—C3—C5—C10 | 57.90 (18) | N2—C1—C17—O1 | −171.47 (13) |
C2—C3—C5—C10 | −117.09 (16) | C2—C1—C17—O1 | 6.9 (2) |
C10—C5—C6—C7 | −0.5 (2) | N2—C1—C17—C18 | 8.3 (2) |
C3—C5—C6—C7 | −178.24 (14) | C2—C1—C17—C18 | −173.32 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6A···N3i | 0.93 | 2.53 | 3.432 (2) | 165 |
C16—H16A···O1ii | 0.93 | 2.59 | 3.3758 (19) | 142 |
Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) x−1/2, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H13N3O |
Mr | 287.31 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 296 |
a, b, c (Å) | 6.8322 (2), 16.8974 (5), 25.7968 (6) |
V (Å3) | 2978.15 (14) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 0.66 |
Crystal size (mm) | 0.56 × 0.35 × 0.23 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.708, 0.863 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10678, 2782, 2338 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.609 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.116, 1.08 |
No. of reflections | 2782 |
No. of parameters | 201 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.17 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6A···N3i | 0.93 | 2.53 | 3.432 (2) | 165 |
C16—H16A···O1ii | 0.93 | 2.59 | 3.3758 (19) | 142 |
Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) x−1/2, y, −z+1/2. |
Acknowledgements
The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University, and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. HKF also thanks King Saud University, Riyadh, Saudi Arabia, for the award of a visiting Professorship (December 23rd 2011 to January 14th 2012).
References
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Owing to the various biological properties of pyrazole derivatives such as anti-cancer (Fu et al., 2010), anti-inflammatory (Bharate et al., 2008) and antimicrobial activities (Thumar & Patel, 2011), we have during the course of our medicinal chemistry research reported the synthesis and bioactivity of pyrazole derivatives (Abdel-Aziz et al., 2009, 2010; Abdel-Wahab et al., 2009). The title compound (I) was synthesized and characterized in order to study the structure activity relationship of this class of compounds.
The molecule of (I), C18H13N3O, has a butterfly-like structure. The pyrazole ring forms the dihedral angles of 59.31 (8) and 57.24 (8)°, respectively, with the C5–C10 and C11–C16 phenyl rings, whereas the dihedral angle between these two rings is 64.03 (8)°. The cabonitrile substituent lies on the same plane with the pyrazole ring with an r.m.s. 0.0027 (1) Å for the seven non-H atoms (C1–C4/N1–N3), whereas the acetyl group is slightly deviated with the torsion angles N2–C1–C17–C18 = 8.3 (2)° and N2–C1–C17–O1 = -171.47 (13)°. The bond distances in (I) are within normal ranges (Allen et al., 1987) and comparable to the related structure (Abdel-Aziz et al., 2011). The crystal packing of (I) is stabilized by weak C—H···N and C—H···O interactions (Table 1). Figure 2 shows the molecular a helical chain along the [1 0 0] linked by these interactions.