Literature DB >> 22219868

4-(1,3-Diphenyl-4,5-dihydro-1H-pyrazol-5-yl)-1,3-diphenyl-1H-pyrazole.

Hoong-Kun Fun, Tze Shyang Chia, Shridhar Malladi, Arun M Isloor, Kammasandra N Shivananda.   

Abstract

The title compound, C(30)H(24)N(4), contains two pyrazole rings and four phenyl rings. The pyrazole rings are essentially planar, with maximum deviations of 0.003 (1) and 0.066 (1) Å and make a dihedral angle of 73.43 (6)°. The two pyrazole rings make dihedral angles of 40.08 (6), 9.28 (6), 15.78 (8) and 17.25 (7)° with their attached phenyl rings. In the crystal, there are no significant inter-molecular hydrogen-bonding inter-actions. The crystal structure is stabilized by C-H⋯π inter-actions.

Entities:  

Year:  2011        PMID: 22219868      PMCID: PMC3247563          DOI: 10.1107/S1600536811039869

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For the pharmacological activity of substituted 2-pyrazolines, see: Sahu et al. (2008 ▶); Farghaly et al. (1990 ▶); Adnan et al. (2005 ▶); Budakoti et al. (2008 ▶); Yar et al. (2007 ▶); Palaska et al. (1996 ▶); Jia et al. (2004 ▶). For the experimental preparation, see: Bratenko et al. (2001 ▶). For related structures, see: Fun et al. (2010 ▶, 2011 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C30H24N4 M = 440.53 Monoclinic, a = 10.7841 (5) Å b = 11.0582 (6) Å c = 21.4820 (9) Å β = 113.359 (2)° V = 2351.82 (19) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 296 K 0.56 × 0.54 × 0.36 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.960, T max = 0.974 22465 measured reflections 7042 independent reflections 5057 reflections with I > 2σ(I) R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.120 S = 1.01 7042 reflections 307 parameters H-atom parameters constrained Δρmax = 0.19 e Å−3 Δρmin = −0.17 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: 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 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039869/kj2190sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039869/kj2190Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811039869/kj2190Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C30H24N4F(000) = 928
Mr = 440.53Dx = 1.244 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6778 reflections
a = 10.7841 (5) Åθ = 2.9–30.3°
b = 11.0582 (6) ŵ = 0.08 mm1
c = 21.4820 (9) ÅT = 296 K
β = 113.359 (2)°Block, colourless
V = 2351.82 (19) Å30.56 × 0.54 × 0.36 mm
Z = 4
Bruker APEX DUO CCD area-detector diffractometer7042 independent reflections
Radiation source: fine-focus sealed tube5057 reflections with I > 2σ(I)
graphiteRint = 0.020
φ and ω scansθmax = 30.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −14→15
Tmin = 0.960, Tmax = 0.974k = −15→15
22465 measured reflectionsl = −30→28
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0521P)2 + 0.329P] where P = (Fo2 + 2Fc2)/3
7042 reflections(Δ/σ)max = 0.001
307 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.17 e Å3
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.
xyzUiso*/Ueq
N10.94191 (8)0.14967 (8)0.85152 (4)0.0419 (2)
N21.01177 (8)0.04544 (8)0.87428 (4)0.0420 (2)
N30.56225 (8)0.05489 (10)0.84967 (4)0.0491 (2)
N40.51695 (9)0.12835 (9)0.88820 (5)0.0455 (2)
C10.49306 (18)0.27780 (16)0.99429 (8)0.0766 (4)
H1A0.45250.30830.95050.092*
C20.4751 (2)0.3365 (2)1.04702 (9)0.0983 (6)
H2A0.42300.40631.03850.118*
C30.53416 (19)0.29191 (19)1.11214 (8)0.0857 (5)
H3A0.52190.33151.14750.103*
C40.61059 (15)0.18962 (16)1.12451 (7)0.0681 (4)
H4A0.65010.15921.16840.082*
C50.62987 (12)0.13063 (13)1.07223 (6)0.0548 (3)
H5A0.68280.06121.08140.066*
C60.57077 (11)0.17416 (12)1.00623 (6)0.0493 (3)
C70.59097 (10)0.10939 (11)0.95147 (5)0.0442 (2)
C80.69495 (11)0.01206 (12)0.96309 (6)0.0495 (3)
H8A0.6731−0.05960.98280.059*
H8B0.78430.04010.99240.059*
C90.68557 (10)−0.01291 (11)0.89089 (5)0.0439 (2)
H9A0.6726−0.09950.88070.053*
C100.80458 (10)0.03321 (10)0.87806 (5)0.0410 (2)
C110.92896 (10)−0.02591 (10)0.89020 (5)0.0396 (2)
C120.97411 (10)−0.14903 (10)0.91534 (5)0.0419 (2)
C130.94926 (13)−0.19930 (12)0.96866 (6)0.0544 (3)
H13A0.8983−0.15680.98760.065*
C141.00005 (17)−0.31211 (13)0.99366 (7)0.0673 (4)
H14A0.9834−0.34491.02950.081*
C151.07492 (15)−0.37602 (13)0.96598 (7)0.0671 (4)
H15A1.1089−0.45180.98310.080*
C161.09970 (13)−0.32790 (12)0.91289 (7)0.0615 (3)
H16A1.1506−0.37110.89420.074*
C171.04886 (11)−0.21513 (11)0.88733 (6)0.0504 (3)
H17A1.0649−0.18340.85110.061*
C181.00229 (11)0.24748 (10)0.83059 (5)0.0429 (2)
C191.13800 (13)0.24282 (13)0.84213 (7)0.0610 (3)
H19A1.19010.17620.86360.073*
C201.19517 (14)0.33842 (14)0.82140 (8)0.0667 (4)
H20A1.28620.33540.82900.080*
C211.12019 (15)0.43753 (13)0.78986 (7)0.0619 (3)
H21A1.15980.50110.77610.074*
C220.98606 (16)0.44169 (13)0.77892 (7)0.0657 (4)
H22A0.93460.50880.75780.079*
C230.92646 (13)0.34718 (12)0.79900 (6)0.0561 (3)
H23A0.83530.35080.79120.067*
C240.81716 (10)0.14420 (11)0.85323 (5)0.0447 (2)
H24A0.75230.20500.83990.054*
C250.51983 (12)−0.05529 (12)0.74638 (6)0.0519 (3)
H25A0.5994−0.09870.76780.062*
C260.43826 (13)−0.07908 (14)0.67931 (6)0.0601 (3)
H26A0.4622−0.14000.65640.072*
C270.32226 (13)−0.01377 (15)0.64623 (6)0.0661 (4)
H27A0.2683−0.02980.60100.079*
C280.28672 (12)0.07572 (15)0.68070 (6)0.0634 (4)
H28A0.20870.12060.65830.076*
C290.36529 (11)0.09971 (12)0.74803 (6)0.0511 (3)
H29A0.33960.15990.77080.061*
C300.48330 (10)0.03349 (10)0.78193 (5)0.0417 (2)
U11U22U33U12U13U23
N10.0377 (4)0.0422 (5)0.0463 (4)0.0033 (4)0.0172 (3)0.0007 (4)
N20.0369 (4)0.0416 (5)0.0467 (4)0.0037 (4)0.0158 (3)0.0003 (4)
N30.0339 (4)0.0674 (7)0.0420 (4)0.0082 (4)0.0110 (3)−0.0068 (4)
N40.0390 (4)0.0527 (6)0.0462 (5)−0.0005 (4)0.0186 (4)−0.0038 (4)
C10.0935 (11)0.0828 (11)0.0567 (7)0.0240 (9)0.0331 (7)0.0010 (7)
C20.1249 (16)0.1000 (14)0.0798 (11)0.0404 (12)0.0507 (11)−0.0055 (10)
C30.0965 (12)0.1080 (14)0.0648 (9)0.0062 (11)0.0450 (9)−0.0180 (9)
C40.0662 (8)0.0947 (11)0.0492 (7)−0.0118 (8)0.0289 (6)−0.0060 (7)
C50.0488 (6)0.0685 (8)0.0501 (6)−0.0091 (6)0.0230 (5)−0.0019 (6)
C60.0452 (6)0.0596 (7)0.0473 (6)−0.0063 (5)0.0230 (5)−0.0048 (5)
C70.0372 (5)0.0518 (6)0.0456 (5)−0.0070 (4)0.0186 (4)−0.0025 (5)
C80.0356 (5)0.0677 (8)0.0440 (5)0.0006 (5)0.0146 (4)0.0007 (5)
C90.0318 (4)0.0536 (6)0.0442 (5)0.0019 (4)0.0129 (4)−0.0013 (5)
C100.0337 (4)0.0474 (6)0.0404 (5)0.0011 (4)0.0132 (4)−0.0033 (4)
C110.0338 (4)0.0442 (6)0.0388 (5)0.0004 (4)0.0121 (4)−0.0027 (4)
C120.0336 (4)0.0435 (6)0.0426 (5)−0.0026 (4)0.0086 (4)−0.0017 (4)
C130.0614 (7)0.0534 (7)0.0468 (6)−0.0032 (6)0.0198 (5)−0.0020 (5)
C140.0897 (10)0.0547 (8)0.0492 (6)−0.0078 (7)0.0187 (6)0.0067 (6)
C150.0713 (8)0.0439 (7)0.0641 (8)0.0017 (6)0.0036 (6)0.0054 (6)
C160.0517 (7)0.0503 (7)0.0751 (8)0.0077 (6)0.0171 (6)−0.0033 (6)
C170.0425 (5)0.0485 (6)0.0598 (7)0.0032 (5)0.0197 (5)0.0025 (5)
C180.0463 (5)0.0430 (6)0.0411 (5)−0.0002 (5)0.0191 (4)−0.0030 (4)
C190.0487 (6)0.0565 (8)0.0801 (9)0.0042 (6)0.0281 (6)0.0130 (7)
C200.0558 (7)0.0690 (9)0.0812 (9)−0.0076 (7)0.0334 (7)0.0055 (7)
C210.0755 (9)0.0559 (8)0.0617 (7)−0.0086 (7)0.0350 (7)0.0027 (6)
C220.0761 (9)0.0554 (8)0.0710 (8)0.0095 (7)0.0349 (7)0.0169 (7)
C230.0534 (6)0.0566 (7)0.0602 (7)0.0079 (6)0.0247 (5)0.0097 (6)
C240.0367 (5)0.0479 (6)0.0493 (5)0.0064 (4)0.0168 (4)−0.0003 (5)
C250.0448 (6)0.0620 (8)0.0486 (6)0.0007 (5)0.0182 (5)−0.0040 (5)
C260.0602 (7)0.0720 (9)0.0511 (6)−0.0144 (6)0.0255 (6)−0.0142 (6)
C270.0547 (7)0.0906 (11)0.0434 (6)−0.0177 (7)0.0093 (5)−0.0051 (6)
C280.0436 (6)0.0807 (10)0.0535 (7)−0.0010 (6)0.0062 (5)0.0092 (7)
C290.0395 (5)0.0578 (7)0.0522 (6)0.0019 (5)0.0141 (5)0.0022 (5)
C300.0326 (4)0.0514 (6)0.0407 (5)−0.0046 (4)0.0141 (4)−0.0004 (4)
N1—N21.3576 (12)C13—H13A0.9300
N1—C241.3617 (14)C14—C151.373 (2)
N1—C181.4241 (14)C14—H14A0.9300
N2—C111.3339 (14)C15—C161.377 (2)
N3—N41.3798 (13)C15—H15A0.9300
N3—C301.3843 (13)C16—C171.3851 (18)
N3—C91.4768 (13)C16—H16A0.9300
N4—C71.2917 (14)C17—H17A0.9300
C1—C61.382 (2)C18—C231.3801 (16)
C1—C21.384 (2)C18—C191.3850 (16)
C1—H1A0.9300C19—C201.3834 (19)
C2—C31.378 (3)C19—H19A0.9300
C2—H2A0.9300C20—C211.371 (2)
C3—C41.362 (3)C20—H20A0.9300
C3—H3A0.9300C21—C221.371 (2)
C4—C51.3839 (19)C21—H21A0.9300
C4—H4A0.9300C22—C231.3826 (19)
C5—C61.3899 (17)C22—H22A0.9300
C5—H5A0.9300C23—H23A0.9300
C6—C71.4653 (16)C24—H24A0.9300
C7—C81.5021 (17)C25—C261.3835 (17)
C8—C91.5388 (15)C25—C301.3931 (17)
C8—H8A0.9700C25—H25A0.9300
C8—H8B0.9700C26—C271.373 (2)
C9—C101.5045 (15)C26—H26A0.9300
C9—H9A0.9800C27—C281.378 (2)
C10—C241.3663 (16)C27—H27A0.9300
C10—C111.4202 (14)C28—C291.3814 (17)
C11—C121.4743 (15)C28—H28A0.9300
C12—C171.3895 (16)C29—C301.3968 (15)
C12—C131.3914 (16)C29—H29A0.9300
C13—C141.382 (2)
N2—N1—C24111.45 (9)C12—C13—H13A119.9
N2—N1—C18120.04 (8)C15—C14—C13120.44 (13)
C24—N1—C18128.50 (9)C15—C14—H14A119.8
C11—N2—N1105.20 (8)C13—C14—H14A119.8
N4—N3—C30120.98 (8)C14—C15—C16120.01 (13)
N4—N3—C9112.84 (8)C14—C15—H15A120.0
C30—N3—C9125.15 (9)C16—C15—H15A120.0
C7—N4—N3108.52 (9)C15—C16—C17119.98 (13)
C6—C1—C2120.52 (15)C15—C16—H16A120.0
C6—C1—H1A119.7C17—C16—H16A120.0
C2—C1—H1A119.7C16—C17—C12120.56 (12)
C3—C2—C1120.35 (17)C16—C17—H17A119.7
C3—C2—H2A119.8C12—C17—H17A119.7
C1—C2—H2A119.8C23—C18—C19119.72 (11)
C4—C3—C2119.68 (15)C23—C18—N1120.40 (10)
C4—C3—H3A120.2C19—C18—N1119.88 (10)
C2—C3—H3A120.2C20—C19—C18119.22 (12)
C3—C4—C5120.46 (14)C20—C19—H19A120.4
C3—C4—H4A119.8C18—C19—H19A120.4
C5—C4—H4A119.8C21—C20—C19121.28 (13)
C4—C5—C6120.60 (14)C21—C20—H20A119.4
C4—C5—H5A119.7C19—C20—H20A119.4
C6—C5—H5A119.7C20—C21—C22119.14 (13)
C1—C6—C5118.38 (12)C20—C21—H21A120.4
C1—C6—C7121.90 (11)C22—C21—H21A120.4
C5—C6—C7119.71 (12)C21—C22—C23120.70 (13)
N4—C7—C6122.61 (11)C21—C22—H22A119.7
N4—C7—C8113.59 (10)C23—C22—H22A119.7
C6—C7—C8123.76 (10)C18—C23—C22119.95 (12)
C7—C8—C9102.40 (9)C18—C23—H23A120.0
C7—C8—H8A111.3C22—C23—H23A120.0
C9—C8—H8A111.3N1—C24—C10107.60 (9)
C7—C8—H8B111.3N1—C24—H24A126.2
C9—C8—H8B111.3C10—C24—H24A126.2
H8A—C8—H8B109.2C26—C25—C30120.24 (12)
N3—C9—C10110.42 (9)C26—C25—H25A119.9
N3—C9—C8101.35 (8)C30—C25—H25A119.9
C10—C9—C8113.82 (9)C27—C26—C25120.76 (13)
N3—C9—H9A110.3C27—C26—H26A119.6
C10—C9—H9A110.3C25—C26—H26A119.6
C8—C9—H9A110.3C26—C27—C28119.33 (11)
C24—C10—C11104.63 (9)C26—C27—H27A120.3
C24—C10—C9126.87 (10)C28—C27—H27A120.3
C11—C10—C9128.49 (10)C27—C28—C29120.97 (12)
N2—C11—C10111.11 (10)C27—C28—H28A119.5
N2—C11—C12118.86 (9)C29—C28—H28A119.5
C10—C11—C12130.02 (10)C28—C29—C30119.94 (12)
C17—C12—C13118.71 (11)C28—C29—H29A120.0
C17—C12—C11119.42 (10)C30—C29—H29A120.0
C13—C12—C11121.80 (10)N3—C30—C25120.47 (10)
C14—C13—C12120.29 (13)N3—C30—C29120.79 (10)
C14—C13—H13A119.9C25—C30—C29118.74 (10)
C24—N1—N2—C110.15 (11)N2—C11—C12—C13138.80 (11)
C18—N1—N2—C11179.35 (9)C10—C11—C12—C13−42.50 (16)
C30—N3—N4—C7163.87 (10)C17—C12—C13—C140.96 (17)
C9—N3—N4—C7−5.10 (13)C11—C12—C13—C14−176.08 (11)
C6—C1—C2—C3−0.3 (3)C12—C13—C14—C15−0.3 (2)
C1—C2—C3—C40.1 (3)C13—C14—C15—C16−0.1 (2)
C2—C3—C4—C50.3 (3)C14—C15—C16—C17−0.1 (2)
C3—C4—C5—C6−0.5 (2)C15—C16—C17—C120.78 (19)
C2—C1—C6—C50.1 (2)C13—C12—C17—C16−1.18 (17)
C2—C1—C6—C7179.55 (16)C11—C12—C17—C16175.93 (10)
C4—C5—C6—C10.28 (19)N2—N1—C18—C23171.28 (10)
C4—C5—C6—C7−179.17 (11)C24—N1—C18—C23−9.67 (17)
N3—N4—C7—C6179.29 (10)N2—N1—C18—C19−8.90 (15)
N3—N4—C7—C8−2.93 (13)C24—N1—C18—C19170.15 (12)
C1—C6—C7—N4−15.00 (19)C23—C18—C19—C20−0.3 (2)
C5—C6—C7—N4164.43 (11)N1—C18—C19—C20179.88 (12)
C1—C6—C7—C8167.43 (13)C18—C19—C20—C210.2 (2)
C5—C6—C7—C8−13.13 (17)C19—C20—C21—C220.2 (2)
N4—C7—C8—C99.08 (13)C20—C21—C22—C23−0.3 (2)
C6—C7—C8—C9−173.16 (10)C19—C18—C23—C220.14 (19)
N4—N3—C9—C10−110.71 (10)N1—C18—C23—C22179.96 (12)
C30—N3—C9—C1080.87 (13)C21—C22—C23—C180.2 (2)
N4—N3—C9—C810.24 (12)N2—N1—C24—C100.20 (12)
C30—N3—C9—C8−158.19 (11)C18—N1—C24—C10−178.92 (10)
C7—C8—C9—N3−10.62 (11)C11—C10—C24—N1−0.44 (11)
C7—C8—C9—C10107.91 (10)C9—C10—C24—N1178.21 (10)
N3—C9—C10—C2422.18 (15)C30—C25—C26—C271.7 (2)
C8—C9—C10—C24−91.02 (13)C25—C26—C27—C28−0.5 (2)
N3—C9—C10—C11−159.50 (10)C26—C27—C28—C29−0.6 (2)
C8—C9—C10—C1187.30 (14)C27—C28—C29—C300.6 (2)
N1—N2—C11—C10−0.43 (11)N4—N3—C30—C25−169.65 (11)
N1—N2—C11—C12178.50 (8)C9—N3—C30—C25−2.11 (17)
C24—C10—C11—N20.55 (12)N4—N3—C30—C299.94 (17)
C9—C10—C11—N2−178.06 (10)C9—N3—C30—C29177.48 (11)
C24—C10—C11—C12−178.22 (10)C26—C25—C30—N3177.86 (11)
C9—C10—C11—C123.16 (18)C26—C25—C30—C29−1.74 (18)
N2—C11—C12—C17−38.22 (14)C28—C29—C30—N3−178.99 (12)
C10—C11—C12—C17140.48 (11)C28—C29—C30—C250.61 (18)
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C8—H8A···Cg1i0.972.953.6999 (15)135
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯AD—HH⋯ADAD—H⋯A
C8—H8ACg1i0.972.953.6999 (15)135

Symmetry code: (i) .

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