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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1638.
Published online 2008 July 31. doi:  10.1107/S160053680801979X
PMCID: PMC2962117

1-[3-(2-Naphth­yl)-5-(3,4,5-trimethoxy­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone

Abstract

In the title compound, C24H24N2O4, the pendant benzene and naphthalene ring systems make dihedral angles of 87.9 (3) and 19.2 (3)°, respectively, with the central pyrazoline ring. In the crystal structure, weak C—H(...)O inter­actions help to establish the packing.

Related literature

For a related structure, see: Lu et al. (2006 [triangle]).

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Object name is e-64-o1638-scheme1.jpg

Experimental

Crystal data

  • C24H24N2O4
  • M r = 404.45
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1638-efi1.jpg
  • a = 12.611 (3) Å
  • b = 15.177 (3) Å
  • c = 10.580 (2) Å
  • β = 92.03 (3)°
  • V = 2023.6 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 113 (2) K
  • 0.14 × 0.12 × 0.10 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 [triangle]) T min = 0.987, T max = 0.991
  • 24346 measured reflections
  • 4655 independent reflections
  • 3976 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.129
  • S = 1.07
  • 4655 reflections
  • 275 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku, 2008 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801979X/hb2755sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801979X/hb2755Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank Dr Haibin Song of Nankai University for helpful discussions and the Science Foundation of GuangXi University for financial support.

supplementary crystallographic information

Comment

The title compound, (I), (Fig. 1) was prepared and structurally characterized as part of our ongoing studies (Lu et al., 2006) of pyrazoline derivatives.

The pendant C14–C19 benzene ring and C1–C10 naphthalene ring make dihedral angles of 87.93 (6) and 19.56 (6)°, respectively, with the N1/N2/C11/C12/C13 pyrazoline ring. The dihedral angle between the benzene ring and naphthalene ring is 77.72 (6)°. Among the three methoxy groups, two are co-planar with the benzene ring, but the O3—C21 bond makes an angle of 31.3 (13)° with the ring, to minimize steric repulson between methoxy groups. The molecule of (I) is chiral: in the arbitrarily chosen asymmetric unit, C13 has S configuration, but crystal symmetry generates a racemic mixture.

In the crystal of (I), the molecules are linked by weak C—H···O interactions (Table 1).

Experimental

A mixture of 1-(naphthalen-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (5.0 mmol), hydrazine hydrate (25.0 mmol) and acetic acid (30 ml) was heated at reflux for 5 h, then poured onto crushed ice. The precipitate was separated by filtration, washed with water, and crystallized from trichloromethane–methanol to obtain the title compound.

The title compound (40 mg) was dissolved in mixture of acetone (10 ml) and water (10 ml) and the solution was kept at room temperature for 10 d. Natural evaporation of the solution gave colourless blocks of (I): Mp. 415–416 K.

Refinement

All H atoms were placed geometrically (C—H = 0.93–0.98 Å), and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Figures

Fig. 1.
The molecular structure of (I), shown with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).

Crystal data

C24H24N2O4F000 = 856
Mr = 404.45Dx = 1.328 Mg m3
Monoclinic, P21/cMelting point = 415–416 K
Hall symbol: -P 2ybcMo Kα radiation λ = 0.71073 Å
a = 12.611 (3) ÅCell parameters from 5898 reflections
b = 15.177 (3) Åθ = 1.9–27.5º
c = 10.580 (2) ŵ = 0.09 mm1
β = 92.03 (3)ºT = 113 (2) K
V = 2023.6 (7) Å3Block, colourless
Z = 40.14 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn diffractometer4655 independent reflections
Radiation source: rotating anode3976 reflections with I > 2σ(I)
Monochromator: confocalRint = 0.040
T = 113(2) Kθmax = 27.5º
ω scansθmin = 1.6º
Absorption correction: multi-scan(CrystalClear; Rigaku, 2008)h = −16→16
Tmin = 0.987, Tmax = 0.991k = −19→19
24346 measured reflectionsl = −13→13

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.129  w = 1/[σ2(Fo2) + (0.0756P)2 + 0.2039P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
4655 reflectionsΔρmax = 0.22 e Å3
275 parametersΔρmin = −0.28 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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.
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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.55819 (8)0.34748 (6)0.49413 (9)0.0273 (2)
O20.26913 (7)0.14553 (6)0.77917 (8)0.0227 (2)
O30.20369 (7)0.09108 (6)0.55062 (9)0.0220 (2)
O40.33628 (7)0.06865 (6)0.36480 (8)0.0234 (2)
N10.72197 (8)0.30131 (7)0.76057 (10)0.0197 (2)
N20.64355 (8)0.29005 (7)0.66497 (10)0.0197 (2)
C10.85205 (10)0.13495 (9)0.95665 (12)0.0216 (3)
H10.80910.08740.93380.026*
C20.93150 (10)0.12422 (9)1.05376 (12)0.0231 (3)
C30.94735 (11)0.04348 (10)1.11946 (13)0.0283 (3)
H30.9034−0.00431.10050.034*
C41.02660 (12)0.03530 (11)1.21027 (14)0.0342 (4)
H41.0357−0.01781.25320.041*
C51.09444 (12)0.10648 (12)1.23931 (14)0.0377 (4)
H51.14880.09991.30030.045*
C61.08098 (11)0.18525 (12)1.17846 (14)0.0351 (4)
H61.12620.23201.19870.042*
C70.99889 (10)0.19670 (10)1.08487 (13)0.0261 (3)
C80.98307 (11)0.27731 (10)1.01867 (14)0.0301 (3)
H81.02700.32501.03800.036*
C90.90514 (10)0.28610 (9)0.92784 (13)0.0253 (3)
H90.89600.33970.88620.030*
C100.83730 (10)0.21415 (9)0.89572 (12)0.0197 (3)
C110.75408 (9)0.22457 (8)0.79621 (12)0.0184 (3)
C120.69637 (10)0.14964 (9)0.73107 (12)0.0214 (3)
H12A0.65010.11950.78830.026*
H12B0.74570.10750.69710.026*
C130.63207 (10)0.19680 (8)0.62438 (12)0.0192 (3)
H130.66780.18870.54450.023*
C140.51784 (10)0.16670 (8)0.60773 (12)0.0184 (3)
C150.48490 (10)0.12988 (8)0.49248 (12)0.0195 (3)
H150.53230.12400.42760.023*
C160.37999 (10)0.10182 (8)0.47523 (11)0.0184 (3)
C170.30944 (10)0.11043 (8)0.57241 (12)0.0184 (3)
C180.34422 (10)0.14469 (8)0.68948 (12)0.0180 (3)
C190.44879 (10)0.17348 (8)0.70697 (12)0.0191 (3)
H190.47210.19700.78420.023*
C200.29410 (12)0.19068 (11)0.89501 (13)0.0322 (3)
H20A0.35590.16460.93530.048*
H20B0.23530.18620.94990.048*
H20C0.30790.25160.87760.048*
C210.17898 (11)−0.00027 (9)0.56046 (13)0.0262 (3)
H21A0.2251−0.03370.50840.039*
H21B0.1066−0.00990.53280.039*
H21C0.1886−0.01880.64690.039*
C220.40060 (12)0.06731 (10)0.25729 (13)0.0293 (3)
H22A0.42840.12520.24320.044*
H22B0.35870.04900.18440.044*
H22C0.45820.02670.27160.044*
C230.61160 (10)0.35986 (9)0.59197 (12)0.0210 (3)
C240.64295 (11)0.45014 (9)0.63730 (13)0.0256 (3)
H24A0.71590.46080.61910.038*
H24B0.63410.45400.72690.038*
H24C0.59890.49340.59500.038*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0283 (5)0.0300 (5)0.0229 (5)−0.0031 (4)−0.0072 (4)0.0026 (4)
O20.0205 (5)0.0269 (5)0.0209 (5)−0.0017 (4)0.0014 (4)−0.0047 (4)
O30.0155 (4)0.0227 (5)0.0273 (5)−0.0014 (3)−0.0041 (4)−0.0010 (4)
O40.0213 (5)0.0314 (5)0.0173 (4)−0.0057 (4)−0.0026 (4)−0.0045 (4)
N10.0154 (5)0.0242 (6)0.0190 (5)−0.0027 (4)−0.0040 (4)−0.0014 (4)
N20.0179 (5)0.0210 (6)0.0199 (5)−0.0032 (4)−0.0055 (4)−0.0011 (4)
C10.0166 (6)0.0257 (7)0.0224 (6)−0.0005 (5)−0.0005 (5)−0.0035 (5)
C20.0167 (6)0.0330 (7)0.0197 (6)0.0049 (5)0.0009 (5)−0.0015 (5)
C30.0237 (7)0.0368 (8)0.0246 (7)0.0074 (6)0.0017 (5)0.0026 (6)
C40.0285 (8)0.0503 (10)0.0239 (7)0.0158 (7)0.0025 (6)0.0060 (7)
C50.0227 (7)0.0669 (12)0.0232 (7)0.0119 (7)−0.0052 (6)0.0027 (7)
C60.0193 (7)0.0589 (10)0.0266 (7)−0.0004 (7)−0.0053 (6)−0.0035 (7)
C70.0164 (6)0.0400 (8)0.0218 (6)0.0012 (6)−0.0015 (5)−0.0030 (6)
C80.0211 (7)0.0354 (8)0.0333 (8)−0.0074 (6)−0.0049 (6)−0.0050 (6)
C90.0214 (7)0.0241 (7)0.0299 (7)−0.0021 (5)−0.0034 (5)−0.0005 (6)
C100.0147 (6)0.0248 (7)0.0195 (6)0.0002 (5)−0.0010 (5)−0.0032 (5)
C110.0151 (6)0.0220 (6)0.0181 (6)−0.0009 (5)0.0001 (5)−0.0016 (5)
C120.0186 (6)0.0219 (7)0.0234 (6)0.0004 (5)−0.0043 (5)−0.0032 (5)
C130.0179 (6)0.0205 (6)0.0191 (6)−0.0011 (5)−0.0017 (5)−0.0033 (5)
C140.0175 (6)0.0161 (6)0.0213 (6)−0.0009 (5)−0.0035 (5)0.0011 (5)
C150.0188 (6)0.0208 (6)0.0188 (6)−0.0010 (5)−0.0004 (5)−0.0008 (5)
C160.0209 (6)0.0170 (6)0.0169 (6)−0.0011 (5)−0.0045 (5)0.0000 (5)
C170.0154 (6)0.0172 (6)0.0222 (6)−0.0002 (5)−0.0035 (5)0.0010 (5)
C180.0189 (6)0.0161 (6)0.0188 (6)0.0019 (5)0.0001 (5)0.0014 (5)
C190.0203 (6)0.0184 (6)0.0182 (6)−0.0005 (5)−0.0039 (5)−0.0013 (5)
C200.0301 (8)0.0429 (9)0.0238 (7)−0.0045 (6)0.0039 (6)−0.0126 (6)
C210.0220 (6)0.0272 (7)0.0292 (7)−0.0074 (5)−0.0013 (5)0.0017 (6)
C220.0327 (8)0.0358 (8)0.0194 (6)−0.0121 (6)0.0029 (6)−0.0063 (6)
C230.0174 (6)0.0248 (7)0.0206 (6)−0.0017 (5)−0.0005 (5)0.0017 (5)
C240.0255 (7)0.0226 (7)0.0286 (7)−0.0018 (5)−0.0016 (6)0.0014 (5)

Geometric parameters (Å, °)

O1—C231.2292 (16)C10—C111.4685 (17)
O2—C181.3642 (16)C11—C121.5040 (18)
O2—C201.4294 (16)C12—C131.5424 (18)
O3—C171.3769 (15)C12—H12A0.9700
O3—C211.4255 (16)C12—H12B0.9700
O4—C161.3699 (15)C13—C141.5155 (17)
O4—C221.4204 (16)C13—H130.9800
N1—C111.2851 (17)C14—C151.3913 (17)
N1—N21.3997 (14)C14—C191.3913 (18)
N2—C231.3636 (17)C15—C161.3957 (17)
N2—C131.4845 (16)C15—H150.9300
C1—C101.3734 (19)C16—C171.3894 (18)
C1—C21.4188 (18)C17—C181.3994 (18)
C1—H10.9300C18—C191.3953 (18)
C2—C31.419 (2)C19—H190.9300
C2—C71.421 (2)C20—H20A0.9600
C3—C41.367 (2)C20—H20B0.9600
C3—H30.9300C20—H20C0.9600
C4—C51.405 (2)C21—H21A0.9600
C4—H40.9300C21—H21B0.9600
C5—C61.366 (2)C21—H21C0.9600
C5—H50.9300C22—H22A0.9600
C6—C71.4175 (19)C22—H22B0.9600
C6—H60.9300C22—H22C0.9600
C7—C81.420 (2)C23—C241.5001 (19)
C8—C91.3565 (19)C24—H24A0.9600
C8—H80.9300C24—H24B0.9600
C9—C101.4210 (18)C24—H24C0.9600
C9—H90.9300
C18—O2—C20117.62 (10)N2—C13—H13109.1
C17—O3—C21114.09 (10)C14—C13—H13109.1
C16—O4—C22117.66 (10)C12—C13—H13109.1
C11—N1—N2107.97 (10)C15—C14—C19121.04 (11)
C23—N2—N1120.09 (10)C15—C14—C13118.42 (11)
C23—N2—C13123.58 (10)C19—C14—C13120.51 (11)
N1—N2—C13112.62 (9)C14—C15—C16119.29 (12)
C10—C1—C2121.38 (12)C14—C15—H15120.4
C10—C1—H1119.3C16—C15—H15120.4
C2—C1—H1119.3O4—C16—C17114.63 (11)
C1—C2—C3122.49 (13)O4—C16—C15125.07 (12)
C1—C2—C7118.68 (12)C17—C16—C15120.23 (11)
C3—C2—C7118.82 (12)O3—C17—C16119.86 (11)
C4—C3—C2120.61 (14)O3—C17—C18119.92 (11)
C4—C3—H3119.7C16—C17—C18120.07 (11)
C2—C3—H3119.7O2—C18—C19125.51 (11)
C3—C4—C5120.53 (15)O2—C18—C17114.56 (11)
C3—C4—H4119.7C19—C18—C17119.92 (12)
C5—C4—H4119.7C14—C19—C18119.38 (11)
C6—C5—C4120.36 (14)C14—C19—H19120.3
C6—C5—H5119.8C18—C19—H19120.3
C4—C5—H5119.8O2—C20—H20A109.5
C5—C6—C7120.80 (15)O2—C20—H20B109.5
C5—C6—H6119.6H20A—C20—H20B109.5
C7—C6—H6119.6O2—C20—H20C109.5
C6—C7—C8122.43 (13)H20A—C20—H20C109.5
C6—C7—C2118.86 (14)H20B—C20—H20C109.5
C8—C7—C2118.69 (12)O3—C21—H21A109.5
C9—C8—C7121.31 (13)O3—C21—H21B109.5
C9—C8—H8119.3H21A—C21—H21B109.5
C7—C8—H8119.3O3—C21—H21C109.5
C8—C9—C10120.58 (13)H21A—C21—H21C109.5
C8—C9—H9119.7H21B—C21—H21C109.5
C10—C9—H9119.7O4—C22—H22A109.5
C1—C10—C9119.34 (12)O4—C22—H22B109.5
C1—C10—C11120.81 (11)H22A—C22—H22B109.5
C9—C10—C11119.84 (12)O4—C22—H22C109.5
N1—C11—C10121.18 (11)H22A—C22—H22C109.5
N1—C11—C12114.11 (11)H22B—C22—H22C109.5
C10—C11—C12124.67 (11)O1—C23—N2120.02 (12)
C11—C12—C13102.58 (10)O1—C23—C24122.63 (12)
C11—C12—H12A111.3N2—C23—C24117.35 (11)
C13—C12—H12A111.3C23—C24—H24A109.5
C11—C12—H12B111.3C23—C24—H24B109.5
C13—C12—H12B111.3H24A—C24—H24B109.5
H12A—C12—H12B109.2C23—C24—H24C109.5
N2—C13—C14113.80 (10)H24A—C24—H24C109.5
N2—C13—C12100.80 (9)H24B—C24—H24C109.5
C14—C13—C12114.71 (11)
C11—N1—N2—C23−166.22 (12)N1—N2—C13—C1212.91 (13)
C11—N1—N2—C13−7.16 (14)C11—C12—C13—N2−12.83 (12)
C10—C1—C2—C3179.06 (12)C11—C12—C13—C14−135.52 (11)
C10—C1—C2—C7−2.04 (19)N2—C13—C14—C15125.51 (12)
C1—C2—C3—C4178.34 (12)C12—C13—C14—C15−119.12 (13)
C7—C2—C3—C4−0.6 (2)N2—C13—C14—C19−56.38 (15)
C2—C3—C4—C5−0.6 (2)C12—C13—C14—C1958.98 (15)
C3—C4—C5—C61.0 (2)C19—C14—C15—C161.96 (19)
C4—C5—C6—C7−0.2 (2)C13—C14—C15—C16−179.94 (11)
C5—C6—C7—C8−179.35 (14)C22—O4—C16—C17173.08 (11)
C5—C6—C7—C2−1.0 (2)C22—O4—C16—C15−3.84 (18)
C1—C2—C7—C6−177.61 (12)C14—C15—C16—O4176.58 (11)
C3—C2—C7—C61.34 (19)C14—C15—C16—C17−0.18 (19)
C1—C2—C7—C80.84 (19)C21—O3—C17—C1683.24 (14)
C3—C2—C7—C8179.79 (13)C21—O3—C17—C18−101.35 (13)
C6—C7—C8—C9178.77 (13)O4—C16—C17—O3−3.74 (16)
C2—C7—C8—C90.4 (2)C15—C16—C17—O3173.34 (11)
C7—C8—C9—C10−0.5 (2)O4—C16—C17—C18−179.15 (11)
C2—C1—C10—C91.98 (19)C15—C16—C17—C18−2.06 (18)
C2—C1—C10—C11−179.40 (11)C20—O2—C18—C199.38 (18)
C8—C9—C10—C1−0.7 (2)C20—O2—C18—C17−171.42 (12)
C8—C9—C10—C11−179.35 (12)O3—C17—C18—O27.90 (16)
N2—N1—C11—C10179.66 (10)C16—C17—C18—O2−176.70 (10)
N2—N1—C11—C12−2.55 (14)O3—C17—C18—C19−172.85 (11)
C1—C10—C11—N1162.71 (12)C16—C17—C18—C192.55 (18)
C9—C10—C11—N1−18.67 (19)C15—C14—C19—C18−1.47 (18)
C1—C10—C11—C12−14.84 (19)C13—C14—C19—C18−179.53 (11)
C9—C10—C11—C12163.78 (12)O2—C18—C19—C14178.36 (11)
N1—C11—C12—C1310.43 (14)C17—C18—C19—C14−0.80 (18)
C10—C11—C12—C13−171.87 (11)N1—N2—C23—O1166.45 (11)
C23—N2—C13—C14−65.56 (16)C13—N2—C23—O19.77 (19)
N1—N2—C13—C14136.22 (11)N1—N2—C23—C24−14.40 (17)
C23—N2—C13—C12171.12 (11)C13—N2—C23—C24−171.08 (11)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C5—H5···O4i0.932.483.3327 (19)152
C8—H8···O3ii0.932.573.4320 (19)155
C12—H12A···O1iii0.972.553.3359 (18)138
C19—H19···O1iii0.932.533.3073 (18)141

Symmetry codes: (i) x+1, y, z+1; (ii) x+1, −y+1/2, z+1/2; (iii) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2755).

References

  • Lu, Z.-K., Li, S. & Huang, P.-M. (2006). Acta Cryst. E62, o5830–o5831.
  • Rigaku (2008). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography