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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o368.
Published online 2010 January 16. doi:  10.1107/S160053680905572X
PMCID: PMC2979729

3-Methyl-5-phenyl-1-(3-phenyl­isoquinolin-1-yl)-1H-pyrazole

Abstract

The title compound, C25H19N3, is composed of an aryl-substituted pyrazole ring connected to an aryl-substituted isoquinoline ring system with a dihedral angle of 52.7 (1)° between the pyrazole ring and the isoquinoline ring system. The dihedral angle between the pyrazole ring and the phenyl ring attached to it is 27.4 (1)° and the dihedral angle between the isoquinoline ring system and the phenyl ring attached to it is 19.6 (1)°.

Related literature

For medicinal applications of hydrazine derivatives, see: Broadhurst et al. (2001 [triangle]).

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Object name is e-66-0o368-scheme1.jpg

Experimental

Crystal data

  • C25H19N3
  • M r = 361.43
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o368-efi1.jpg
  • a = 10.9610 (9) Å
  • b = 16.8078 (13) Å
  • c = 21.3118 (17) Å
  • V = 3926.3 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 290 K
  • 0.42 × 0.23 × 0.20 mm

Data collection

  • Bruker SMART area-detector diffractometer
  • 26302 measured reflections
  • 3452 independent reflections
  • 2031 reflections with I > 2σ(I)
  • R int = 0.091

Refinement

  • R[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.172
  • S = 1.04
  • 3452 reflections
  • 254 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680905572X/bt5159sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905572X/bt5159Isup2.hkl

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

Acknowledgments

We thank the Department of Science and Technology, India, for use of the diffraction facility at IISc under the IRHPA–DST program. FNK thanks the DST for Fast Track Proposal funding. We thank VIT University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

3-Phenylisoquinolin-1-ylhydrazine (2.35 g, 10 mmol) and 1-phenylbutane-1,3-dione (1.62 g, 10 mmol) were dissolved in ethanol (30 ml). The solution was heated for 12 h under a nitrogen atmosphere. The reaction was quenched with water; the compound was extracted with ethyl acetate. The ethyl acetate phase was washed with water, dried, concentrated and purified by column chromatography to yield a white powder. Crystals were obtained upon recrystallization from dichloromethane.

Refinement

Hydrogen atoms were placed in calculated positions (C–H 0.93–0.96 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C).

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of C25H19N3 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C25H19N3F(000) = 1520
Mr = 361.43Dx = 1.223 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 1667 reflections
a = 10.9610 (9) Åθ = 2.4–19.5°
b = 16.8078 (13) ŵ = 0.07 mm1
c = 21.3118 (17) ÅT = 290 K
V = 3926.3 (5) Å3Block, colorless
Z = 80.42 × 0.23 × 0.20 mm

Data collection

Bruker SMART area-detector diffractometer2031 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.091
graphiteθmax = 25.0°, θmin = 1.9°
[var phi] and ω scansh = −13→13
26302 measured reflectionsk = −19→19
3452 independent reflectionsl = −25→25

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0822P)2 + 0.3609P] where P = (Fo2 + 2Fc2)/3
3452 reflections(Δ/σ)max = 0.001
254 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = −0.16 e Å3

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

xyzUiso*/Ueq
N10.42399 (17)0.56804 (11)0.65341 (8)0.0632 (5)
N20.58627 (17)0.61748 (12)0.59624 (9)0.0707 (6)
N30.70861 (18)0.60123 (14)0.60212 (10)0.0846 (7)
C10.5164 (2)0.61722 (15)0.65309 (11)0.0634 (6)
C20.5528 (2)0.66672 (14)0.70362 (11)0.0633 (6)
C30.6493 (2)0.72259 (17)0.70207 (14)0.0799 (8)
H30.69400.72930.66540.096*
C40.6771 (3)0.76627 (17)0.75330 (18)0.0925 (9)
H40.74140.80230.75170.111*
C50.6101 (3)0.75780 (18)0.80879 (16)0.0963 (9)
H50.63040.78810.84380.116*
C60.5156 (3)0.70560 (18)0.81196 (14)0.0876 (8)
H60.47130.70060.84900.105*
C70.4844 (2)0.65902 (14)0.75938 (11)0.0681 (6)
C80.3851 (2)0.60570 (14)0.75944 (11)0.0691 (7)
H80.33920.59930.79580.083*
C90.3554 (2)0.56334 (14)0.70713 (11)0.0617 (6)
C100.2482 (2)0.50980 (14)0.70392 (11)0.0635 (6)
C110.1918 (2)0.48178 (15)0.75749 (12)0.0745 (7)
H110.22260.49580.79660.089*
C120.0904 (3)0.43317 (16)0.75384 (15)0.0858 (8)
H120.05380.41490.79050.103*
C130.0441 (3)0.4121 (2)0.69771 (17)0.0999 (10)
H13−0.02410.37930.69550.120*
C140.0978 (3)0.4392 (2)0.64406 (16)0.1194 (12)
H140.06600.42480.60520.143*
C150.1993 (3)0.4880 (2)0.64698 (13)0.0944 (9)
H150.23500.50620.61010.113*
C160.8797 (3)0.5726 (3)0.53211 (16)0.1305 (13)
H16A0.92020.56390.57150.196*
H16B0.91710.61660.51080.196*
H16C0.88640.52570.50670.196*
C170.7463 (2)0.59087 (19)0.54383 (14)0.0888 (8)
C180.6524 (3)0.59926 (17)0.50078 (13)0.0849 (8)
H180.65790.59460.45740.102*
C190.5500 (2)0.61580 (14)0.53516 (12)0.0688 (7)
C200.4262 (2)0.63444 (15)0.51195 (12)0.0700 (7)
C210.3472 (3)0.68436 (17)0.54353 (13)0.0869 (8)
H210.37040.70680.58160.104*
C220.2326 (3)0.7011 (2)0.51841 (16)0.1031 (10)
H220.17920.73350.54070.124*
C230.1976 (3)0.6712 (2)0.46237 (18)0.1081 (10)
H230.12140.68350.44580.130*
C240.2752 (3)0.6231 (2)0.43068 (16)0.1117 (11)
H240.25220.60270.39190.134*
C250.3885 (3)0.60395 (18)0.45521 (13)0.0887 (8)
H250.43980.57000.43300.106*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0544 (11)0.0749 (13)0.0603 (12)0.0075 (10)0.0015 (10)0.0039 (9)
N20.0542 (12)0.0933 (15)0.0646 (13)0.0066 (11)0.0042 (10)0.0105 (10)
N30.0552 (13)0.1212 (19)0.0773 (15)0.0096 (12)0.0066 (11)0.0139 (13)
C10.0534 (13)0.0770 (16)0.0598 (15)0.0118 (13)0.0008 (11)0.0094 (12)
C20.0553 (14)0.0668 (15)0.0679 (16)0.0089 (12)−0.0046 (12)0.0053 (12)
C30.0663 (16)0.0801 (18)0.093 (2)0.0056 (15)−0.0055 (14)0.0093 (15)
C40.0795 (19)0.0796 (19)0.118 (3)−0.0061 (15)−0.0244 (19)0.0043 (19)
C50.100 (2)0.090 (2)0.099 (3)0.0029 (19)−0.0241 (19)−0.0117 (17)
C60.091 (2)0.091 (2)0.081 (2)0.0016 (18)−0.0062 (15)−0.0128 (15)
C70.0642 (14)0.0718 (15)0.0682 (17)0.0086 (13)−0.0041 (13)−0.0033 (13)
C80.0652 (15)0.0802 (17)0.0619 (16)0.0128 (13)0.0063 (12)−0.0027 (13)
C90.0550 (13)0.0701 (15)0.0600 (15)0.0128 (12)0.0043 (11)0.0010 (12)
C100.0557 (13)0.0697 (15)0.0652 (16)0.0103 (12)0.0054 (12)−0.0026 (12)
C110.0721 (16)0.0797 (17)0.0717 (17)0.0030 (14)0.0063 (14)0.0030 (13)
C120.0782 (18)0.0835 (18)0.096 (2)0.0000 (15)0.0207 (17)0.0067 (16)
C130.076 (2)0.113 (2)0.110 (3)−0.0224 (17)0.0062 (18)−0.002 (2)
C140.102 (2)0.164 (3)0.092 (2)−0.051 (2)−0.0043 (19)−0.012 (2)
C150.0830 (18)0.129 (3)0.0713 (18)−0.0221 (18)0.0066 (15)−0.0034 (17)
C160.0710 (19)0.202 (4)0.119 (3)0.025 (2)0.0287 (18)0.014 (3)
C170.0685 (17)0.121 (2)0.0765 (19)0.0118 (16)0.0171 (15)0.0141 (17)
C180.0853 (19)0.106 (2)0.0633 (16)0.0106 (16)0.0141 (15)0.0110 (14)
C190.0733 (16)0.0701 (16)0.0630 (16)0.0038 (13)0.0045 (13)0.0093 (12)
C200.0748 (16)0.0685 (15)0.0667 (17)0.0027 (13)0.0002 (14)0.0110 (12)
C210.091 (2)0.093 (2)0.0768 (18)0.0228 (17)−0.0073 (15)0.0028 (14)
C220.097 (2)0.121 (3)0.091 (2)0.0377 (19)−0.0039 (19)0.0170 (18)
C230.084 (2)0.144 (3)0.097 (3)0.017 (2)−0.0086 (19)0.022 (2)
C240.101 (2)0.145 (3)0.089 (2)−0.005 (2)−0.024 (2)−0.004 (2)
C250.089 (2)0.102 (2)0.0748 (19)0.0065 (17)−0.0030 (16)−0.0044 (15)

Geometric parameters (Å, °)

N1—C11.308 (3)C12—H120.9300
N1—C91.372 (3)C13—C141.365 (4)
N2—C191.362 (3)C13—H130.9300
N2—N31.374 (3)C14—C151.383 (4)
N2—C11.433 (3)C14—H140.9300
N3—C171.321 (3)C15—H150.9300
C1—C21.418 (3)C16—C171.515 (4)
C2—C71.411 (3)C16—H16A0.9600
C2—C31.414 (3)C16—H16B0.9600
C3—C41.351 (4)C16—H16C0.9600
C3—H30.9300C17—C181.385 (4)
C4—C51.399 (4)C18—C191.370 (3)
C4—H40.9300C18—H180.9300
C5—C61.359 (4)C19—C201.478 (3)
C5—H50.9300C20—C251.377 (3)
C6—C71.409 (3)C20—C211.381 (4)
C6—H60.9300C21—C221.394 (4)
C7—C81.410 (3)C21—H210.9300
C8—C91.362 (3)C22—C231.351 (4)
C8—H80.9300C22—H220.9300
C9—C101.481 (3)C23—C241.355 (5)
C10—C151.376 (3)C23—H230.9300
C10—C111.381 (3)C24—C251.385 (4)
C11—C121.382 (4)C24—H240.9300
C11—H110.9300C25—H250.9300
C12—C131.347 (4)
C1—N1—C9117.7 (2)C12—C13—H13120.2
C19—N2—N3111.61 (19)C14—C13—H13120.2
C19—N2—C1130.7 (2)C13—C14—C15120.5 (3)
N3—N2—C1116.34 (19)C13—C14—H14119.7
C17—N3—N2104.2 (2)C15—C14—H14119.8
N1—C1—C2125.8 (2)C10—C15—C14120.7 (3)
N1—C1—N2114.9 (2)C10—C15—H15119.6
C2—C1—N2119.3 (2)C14—C15—H15119.6
C7—C2—C3118.5 (2)C17—C16—H16A109.5
C7—C2—C1115.9 (2)C17—C16—H16B109.5
C3—C2—C1125.6 (2)H16A—C16—H16B109.5
C4—C3—C2120.7 (3)C17—C16—H16C109.5
C4—C3—H3119.6H16A—C16—H16C109.5
C2—C3—H3119.6H16B—C16—H16C109.5
C3—C4—C5120.6 (3)N3—C17—C18112.2 (2)
C3—C4—H4119.7N3—C17—C16118.9 (3)
C5—C4—H4119.7C18—C17—C16128.9 (3)
C6—C5—C4120.5 (3)C19—C18—C17106.0 (2)
C6—C5—H5119.7C19—C18—H18127.0
C4—C5—H5119.7C17—C18—H18127.0
C5—C6—C7120.3 (3)N2—C19—C18106.0 (2)
C5—C6—H6119.9N2—C19—C20125.7 (2)
C7—C6—H6119.9C18—C19—C20128.1 (2)
C8—C7—C2118.0 (2)C25—C20—C21117.8 (3)
C8—C7—C6122.7 (2)C25—C20—C19119.4 (2)
C2—C7—C6119.3 (2)C21—C20—C19122.8 (2)
C9—C8—C7121.1 (2)C20—C21—C22120.0 (3)
C9—C8—H8119.5C20—C21—H21120.0
C7—C8—H8119.5C22—C21—H21120.0
C8—C9—N1121.5 (2)C23—C22—C21121.4 (3)
C8—C9—C10123.0 (2)C23—C22—H22119.3
N1—C9—C10115.5 (2)C21—C22—H22119.3
C15—C10—C11117.6 (2)C22—C23—C24118.9 (3)
C15—C10—C9120.8 (2)C22—C23—H23120.5
C11—C10—C9121.6 (2)C24—C23—H23120.5
C12—C11—C10121.0 (2)C23—C24—C25120.9 (3)
C12—C11—H11119.5C23—C24—H24119.5
C10—C11—H11119.5C25—C24—H24119.5
C13—C12—C11120.6 (3)C20—C25—C24120.9 (3)
C13—C12—H12119.7C20—C25—H25119.5
C11—C12—H12119.7C24—C25—H25119.5
C12—C13—C14119.6 (3)
C19—N2—N3—C170.9 (3)N1—C9—C10—C11161.5 (2)
C1—N2—N3—C17169.0 (2)C15—C10—C11—C120.4 (4)
C9—N1—C1—C20.0 (3)C9—C10—C11—C12178.7 (2)
C9—N1—C1—N2178.25 (18)C10—C11—C12—C13−0.1 (4)
C19—N2—C1—N142.3 (3)C11—C12—C13—C14−0.1 (5)
N3—N2—C1—N1−123.0 (2)C12—C13—C14—C150.1 (5)
C19—N2—C1—C2−139.3 (2)C11—C10—C15—C14−0.4 (4)
N3—N2—C1—C255.3 (3)C9—C10—C15—C14−178.7 (3)
N1—C1—C2—C72.4 (3)C13—C14—C15—C100.2 (5)
N2—C1—C2—C7−175.80 (18)N2—N3—C17—C18−0.5 (3)
N1—C1—C2—C3−176.8 (2)N2—N3—C17—C16179.2 (3)
N2—C1—C2—C35.1 (3)N3—C17—C18—C19−0.1 (3)
C7—C2—C3—C41.6 (3)C16—C17—C18—C19−179.8 (3)
C1—C2—C3—C4−179.3 (2)N3—N2—C19—C18−1.0 (3)
C2—C3—C4—C5−0.8 (4)C1—N2—C19—C18−166.9 (2)
C3—C4—C5—C6−0.2 (4)N3—N2—C19—C20−176.8 (2)
C4—C5—C6—C70.4 (4)C1—N2—C19—C2017.3 (4)
C3—C2—C7—C8177.2 (2)C17—C18—C19—N20.6 (3)
C1—C2—C7—C8−2.0 (3)C17—C18—C19—C20176.3 (3)
C3—C2—C7—C6−1.4 (3)N2—C19—C20—C25−156.5 (2)
C1—C2—C7—C6179.4 (2)C18—C19—C20—C2528.6 (4)
C5—C6—C7—C8−178.1 (2)N2—C19—C20—C2126.4 (4)
C5—C6—C7—C20.4 (4)C18—C19—C20—C21−148.5 (3)
C2—C7—C8—C9−0.5 (3)C25—C20—C21—C221.3 (4)
C6—C7—C8—C9178.0 (2)C19—C20—C21—C22178.5 (2)
C7—C8—C9—N13.1 (3)C20—C21—C22—C23−2.0 (5)
C7—C8—C9—C10−176.8 (2)C21—C22—C23—C241.0 (5)
C1—N1—C9—C8−2.8 (3)C22—C23—C24—C250.6 (6)
C1—N1—C9—C10177.05 (19)C21—C20—C25—C240.3 (4)
C8—C9—C10—C15159.6 (2)C19—C20—C25—C24−177.0 (3)
N1—C9—C10—C15−20.2 (3)C23—C24—C25—C20−1.2 (5)
C8—C9—C10—C11−18.6 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5159).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Broadhurst, M. J., Johnson, W. H. & Walter, D. S. (2001). US Patent No. 6235787.
  • Bruker (2004). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). publCIF In preparation.

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