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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o369.
Published online 2010 January 16. doi:  10.1107/S1600536809055718
PMCID: PMC2979751

1-[3-(4-Chloro­phen­yl)isoquinolin-1-yl]-3,5-diphenyl-1H-pyrazole

Abstract

The title compound, C30H20ClN3, is composed of a diaryl-substituted pyrazole ring connected to an aryl-substituted isoquinoline ring system with a dihedral angle of 65.1 (1)° between the pyrazole ring and the isoquinoline ring system. The 3-phenyl and 4-phenyl substitutents are twisted by 8.1 (1) and 43.0 (1)°, respectively, with respect to the pyrazole ring. The chloro­phenyl ring and the isoquinoline ring system are twisted by 21.2 (1)° with respect to each other.

Related literature

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

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Object name is e-66-0o369-scheme1.jpg

Experimental

Crystal data

  • C30H20ClN3
  • M r = 457.94
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o369-efi1.jpg
  • a = 23.7864 (15) Å
  • b = 11.7101 (8) Å
  • c = 8.3602 (5) Å
  • β = 96.738 (1)°
  • V = 2312.6 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.19 mm−1
  • T = 290 K
  • 0.20 × 0.16 × 0.04 mm

Data collection

  • Bruker SMART area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.963, T max = 0.993
  • 17230 measured reflections
  • 4392 independent reflections
  • 2890 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.126
  • S = 1.02
  • 4392 reflections
  • 307 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.19 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/S1600536809055718/bt5160sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055718/bt5160Isup2.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

1-[3-(4-Chlorophenyl)isoquinolin-1-yl]hydrazine (2.69 g, 10 mmol) and 1,3-diphenylpropane-1,3-dione (2.24 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 were obtained upon recrystallization from dichloromethane.

Refinement

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

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of C30H20ClN3 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C30H20ClN3F(000) = 952
Mr = 457.94Dx = 1.315 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3042 reflections
a = 23.7864 (15) Åθ = 2.4–21.9°
b = 11.7101 (8) ŵ = 0.19 mm1
c = 8.3602 (5) ÅT = 290 K
β = 96.738 (1)°Plate, colorless
V = 2312.6 (3) Å30.20 × 0.16 × 0.04 mm
Z = 4

Data collection

Bruker SMART area-detector diffractometer4392 independent reflections
Radiation source: fine-focus sealed tube2890 reflections with I > 2σ(I)
graphiteRint = 0.039
[var phi] and ω scansθmax = 25.7°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −29→26
Tmin = 0.963, Tmax = 0.993k = −14→14
17230 measured reflectionsl = −10→10

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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0562P)2 + 0.2618P] where P = (Fo2 + 2Fc2)/3
4392 reflections(Δ/σ)max = 0.001
307 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = −0.19 e Å3

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

xyzUiso*/Ueq
Cl10.50745 (3)0.63807 (9)1.25356 (11)0.1273 (4)
N10.26392 (7)0.53740 (12)0.79095 (19)0.0492 (4)
N20.19665 (7)0.41903 (13)0.65629 (19)0.0491 (4)
N30.14743 (7)0.38380 (13)0.70881 (19)0.0528 (4)
C10.21697 (9)0.53202 (15)0.6937 (2)0.0464 (5)
C20.18694 (9)0.62628 (16)0.6200 (2)0.0474 (5)
C30.13772 (9)0.61722 (18)0.5098 (2)0.0575 (6)
H30.12200.54590.48430.069*
C40.11301 (10)0.7131 (2)0.4401 (3)0.0649 (6)
H40.08060.70670.36680.078*
C50.13619 (11)0.82097 (19)0.4784 (3)0.0657 (6)
H50.11880.88560.43050.079*
C60.18349 (10)0.83272 (17)0.5840 (3)0.0604 (6)
H60.19820.90510.60810.072*
C70.21069 (9)0.73527 (16)0.6579 (2)0.0495 (5)
C80.26116 (9)0.74042 (16)0.7625 (2)0.0545 (5)
H80.27750.81110.78910.065*
C90.28696 (9)0.64306 (16)0.8263 (2)0.0486 (5)
C100.34144 (9)0.64280 (17)0.9322 (2)0.0530 (5)
C110.36151 (10)0.73945 (19)1.0167 (3)0.0661 (6)
H110.34010.80611.00780.079*
C120.41255 (12)0.7383 (2)1.1135 (3)0.0797 (7)
H120.42550.80381.16910.096*
C130.44384 (10)0.6405 (3)1.1273 (3)0.0770 (7)
C140.42564 (10)0.5433 (2)1.0454 (3)0.0756 (7)
H140.44740.47721.05490.091*
C150.37442 (10)0.54535 (19)0.9486 (3)0.0638 (6)
H150.36180.47960.89320.077*
C160.22447 (8)0.33297 (15)0.5886 (2)0.0457 (5)
C170.19129 (9)0.23868 (16)0.5973 (2)0.0503 (5)
H170.19850.16580.56060.060*
C180.14428 (8)0.27279 (15)0.6720 (2)0.0469 (5)
C190.09634 (8)0.20395 (16)0.7112 (2)0.0487 (5)
C200.05671 (10)0.24761 (19)0.8028 (3)0.0621 (6)
H200.06020.32260.83930.075*
C210.01216 (10)0.1822 (2)0.8410 (3)0.0750 (7)
H21−0.01370.21290.90440.090*
C220.00553 (11)0.0715 (2)0.7861 (3)0.0740 (7)
H22−0.02480.02750.81130.089*
C230.04403 (11)0.02741 (19)0.6942 (3)0.0742 (7)
H230.0398−0.04700.65580.089*
C240.08906 (10)0.09214 (17)0.6579 (3)0.0645 (6)
H240.11520.06030.59630.077*
C250.27834 (9)0.34958 (15)0.5214 (2)0.0479 (5)
C260.28817 (10)0.44330 (17)0.4282 (3)0.0641 (6)
H260.25970.49710.40390.077*
C270.33964 (12)0.45783 (19)0.3709 (3)0.0758 (7)
H270.34570.52170.30900.091*
C280.38175 (11)0.3795 (2)0.4041 (3)0.0734 (7)
H280.41670.39020.36690.088*
C290.37204 (11)0.2852 (2)0.4925 (3)0.0769 (7)
H290.40040.23060.51390.092*
C300.32081 (9)0.26987 (18)0.5502 (3)0.0646 (6)
H300.31480.20480.60960.078*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0696 (5)0.1876 (10)0.1191 (7)−0.0076 (5)−0.0121 (4)−0.0404 (6)
N10.0585 (11)0.0386 (9)0.0517 (10)−0.0025 (8)0.0112 (9)−0.0036 (7)
N20.0550 (11)0.0364 (9)0.0564 (10)−0.0014 (8)0.0090 (8)−0.0034 (7)
N30.0581 (11)0.0424 (10)0.0585 (10)−0.0037 (8)0.0096 (9)−0.0011 (8)
C10.0581 (13)0.0349 (11)0.0483 (11)−0.0019 (9)0.0153 (10)−0.0056 (8)
C20.0565 (13)0.0421 (11)0.0463 (11)0.0043 (10)0.0169 (10)−0.0021 (9)
C30.0660 (15)0.0528 (13)0.0557 (12)0.0036 (11)0.0153 (11)−0.0019 (10)
C40.0685 (16)0.0687 (16)0.0585 (13)0.0150 (13)0.0119 (11)0.0035 (11)
C50.0850 (18)0.0551 (14)0.0603 (14)0.0241 (13)0.0230 (13)0.0083 (11)
C60.0831 (17)0.0393 (12)0.0626 (13)0.0115 (11)0.0248 (13)0.0002 (10)
C70.0627 (14)0.0396 (11)0.0497 (11)0.0039 (10)0.0221 (10)−0.0024 (9)
C80.0692 (15)0.0357 (11)0.0620 (13)−0.0058 (10)0.0225 (12)−0.0077 (9)
C90.0576 (13)0.0406 (12)0.0509 (11)−0.0055 (10)0.0191 (10)−0.0069 (9)
C100.0591 (14)0.0510 (13)0.0514 (12)−0.0087 (10)0.0171 (10)−0.0048 (10)
C110.0729 (17)0.0604 (14)0.0668 (15)−0.0103 (12)0.0166 (13)−0.0143 (11)
C120.0724 (18)0.093 (2)0.0762 (17)−0.0232 (16)0.0188 (14)−0.0332 (14)
C130.0535 (15)0.110 (2)0.0684 (16)−0.0136 (15)0.0116 (12)−0.0142 (15)
C140.0608 (17)0.0819 (18)0.0838 (17)−0.0015 (13)0.0074 (14)−0.0025 (14)
C150.0633 (15)0.0564 (14)0.0724 (15)−0.0081 (12)0.0105 (12)−0.0051 (11)
C160.0517 (12)0.0366 (11)0.0475 (11)0.0026 (9)0.0009 (9)−0.0013 (8)
C170.0600 (14)0.0337 (11)0.0557 (12)0.0010 (10)0.0011 (10)−0.0030 (9)
C180.0543 (13)0.0386 (11)0.0461 (11)−0.0010 (9)−0.0012 (9)0.0008 (8)
C190.0505 (12)0.0454 (12)0.0479 (11)−0.0014 (10)−0.0037 (9)0.0056 (9)
C200.0647 (15)0.0594 (14)0.0625 (14)−0.0055 (12)0.0082 (12)−0.0038 (11)
C210.0671 (17)0.0862 (19)0.0739 (16)−0.0064 (14)0.0178 (13)−0.0008 (14)
C220.0609 (16)0.0766 (18)0.0824 (17)−0.0146 (14)0.0000 (14)0.0200 (14)
C230.0715 (17)0.0490 (14)0.1004 (19)−0.0119 (13)0.0028 (15)0.0067 (13)
C240.0656 (15)0.0432 (13)0.0849 (16)−0.0042 (11)0.0090 (12)−0.0001 (11)
C250.0546 (13)0.0377 (11)0.0503 (11)0.0008 (9)0.0019 (9)−0.0062 (8)
C260.0801 (17)0.0449 (12)0.0722 (15)0.0134 (11)0.0285 (13)0.0067 (10)
C270.100 (2)0.0476 (14)0.0877 (17)0.0030 (14)0.0450 (16)0.0004 (12)
C280.0662 (16)0.0680 (16)0.0895 (18)−0.0083 (14)0.0239 (13)−0.0155 (14)
C290.0578 (16)0.0710 (17)0.1009 (19)0.0112 (13)0.0049 (14)0.0056 (15)
C300.0579 (15)0.0520 (13)0.0829 (16)0.0016 (11)0.0034 (12)0.0113 (11)

Geometric parameters (Å, °)

Cl1—C131.740 (3)C14—H140.9300
N1—C11.304 (2)C15—H150.9300
N1—C91.371 (2)C16—C171.364 (2)
N2—N31.362 (2)C16—C251.471 (3)
N2—C161.364 (2)C17—C181.401 (3)
N2—C11.431 (2)C17—H170.9300
N3—C181.336 (2)C18—C191.465 (3)
C1—C21.416 (3)C19—C201.380 (3)
C2—C31.406 (3)C19—C241.387 (3)
C2—C71.416 (3)C20—C211.375 (3)
C3—C41.366 (3)C20—H200.9300
C3—H30.9300C21—C221.378 (3)
C4—C51.400 (3)C21—H210.9300
C4—H40.9300C22—C231.364 (3)
C5—C61.353 (3)C22—H220.9300
C5—H50.9300C23—C241.375 (3)
C6—C71.417 (3)C23—H230.9300
C6—H60.9300C24—H240.9300
C7—C81.401 (3)C25—C301.376 (3)
C8—C91.373 (3)C25—C261.382 (3)
C8—H80.9300C26—C271.377 (3)
C9—C101.481 (3)C26—H260.9300
C10—C151.382 (3)C27—C281.363 (3)
C10—C111.389 (3)C27—H270.9300
C11—C121.378 (3)C28—C291.363 (3)
C11—H110.9300C28—H280.9300
C12—C131.364 (3)C29—C301.374 (3)
C12—H120.9300C29—H290.9300
C13—C141.372 (3)C30—H300.9300
C14—C151.381 (3)
C1—N1—C9118.01 (16)C14—C15—H15119.2
N3—N2—C16112.77 (15)C10—C15—H15119.2
N3—N2—C1119.41 (15)C17—C16—N2105.32 (17)
C16—N2—C1127.30 (17)C17—C16—C25131.50 (18)
C18—N3—N2104.34 (15)N2—C16—C25123.17 (16)
N1—C1—C2125.82 (17)C16—C17—C18106.85 (17)
N1—C1—N2115.07 (16)C16—C17—H17126.6
C2—C1—N2119.07 (18)C18—C17—H17126.6
C3—C2—C1124.39 (18)N3—C18—C17110.72 (17)
C3—C2—C7119.60 (18)N3—C18—C19120.53 (18)
C1—C2—C7115.95 (19)C17—C18—C19128.74 (18)
C4—C3—C2120.1 (2)C20—C19—C24117.39 (19)
C4—C3—H3120.0C20—C19—C18121.37 (19)
C2—C3—H3120.0C24—C19—C18121.24 (19)
C3—C4—C5120.4 (2)C21—C20—C19121.2 (2)
C3—C4—H4119.8C21—C20—H20119.4
C5—C4—H4119.8C19—C20—H20119.4
C6—C5—C4121.0 (2)C20—C21—C22120.5 (2)
C6—C5—H5119.5C20—C21—H21119.7
C4—C5—H5119.5C22—C21—H21119.7
C5—C6—C7120.3 (2)C23—C22—C21119.1 (2)
C5—C6—H6119.8C23—C22—H22120.5
C7—C6—H6119.8C21—C22—H22120.5
C8—C7—C2117.93 (17)C22—C23—C24120.5 (2)
C8—C7—C6123.46 (19)C22—C23—H23119.8
C2—C7—C6118.6 (2)C24—C23—H23119.8
C9—C8—C7121.21 (18)C23—C24—C19121.4 (2)
C9—C8—H8119.4C23—C24—H24119.3
C7—C8—H8119.4C19—C24—H24119.3
C8—C9—N1121.08 (19)C30—C25—C26117.9 (2)
C8—C9—C10123.64 (18)C30—C25—C16119.88 (18)
N1—C9—C10115.25 (17)C26—C25—C16122.21 (18)
C15—C10—C11117.7 (2)C27—C26—C25120.7 (2)
C15—C10—C9120.50 (19)C27—C26—H26119.6
C11—C10—C9121.8 (2)C25—C26—H26119.6
C12—C11—C10121.2 (2)C28—C27—C26120.6 (2)
C12—C11—H11119.4C28—C27—H27119.7
C10—C11—H11119.4C26—C27—H27119.7
C13—C12—C11119.5 (2)C29—C28—C27119.2 (2)
C13—C12—H12120.3C29—C28—H28120.4
C11—C12—H12120.3C27—C28—H28120.4
C12—C13—C14121.2 (2)C28—C29—C30120.6 (2)
C12—C13—Cl1119.5 (2)C28—C29—H29119.7
C14—C13—Cl1119.4 (2)C30—C29—H29119.7
C13—C14—C15118.9 (2)C29—C30—C25120.9 (2)
C13—C14—H14120.5C29—C30—H30119.6
C15—C14—H14120.5C25—C30—H30119.6
C14—C15—C10121.6 (2)
C16—N2—N3—C18−0.4 (2)Cl1—C13—C14—C15178.42 (18)
C1—N2—N3—C18−172.66 (16)C13—C14—C15—C100.3 (3)
C9—N1—C1—C2−0.1 (3)C11—C10—C15—C140.0 (3)
C9—N1—C1—N2177.32 (15)C9—C10—C15—C14179.37 (19)
N3—N2—C1—N1113.25 (19)N3—N2—C16—C170.5 (2)
C16—N2—C1—N1−57.8 (2)C1—N2—C16—C17172.00 (18)
N3—N2—C1—C2−69.1 (2)N3—N2—C16—C25179.40 (17)
C16—N2—C1—C2119.8 (2)C1—N2—C16—C25−9.0 (3)
N1—C1—C2—C3176.97 (18)N2—C16—C17—C18−0.3 (2)
N2—C1—C2—C3−0.4 (3)C25—C16—C17—C18−179.16 (19)
N1—C1—C2—C7−0.3 (3)N2—N3—C18—C170.1 (2)
N2—C1—C2—C7−177.68 (16)N2—N3—C18—C19179.74 (16)
C1—C2—C3—C4−177.35 (18)C16—C17—C18—N30.1 (2)
C7—C2—C3—C4−0.1 (3)C16—C17—C18—C19−179.44 (18)
C2—C3—C4—C5−0.4 (3)N3—C18—C19—C20−7.5 (3)
C3—C4—C5—C60.4 (3)C17—C18—C19—C20172.01 (19)
C4—C5—C6—C70.2 (3)N3—C18—C19—C24172.62 (18)
C3—C2—C7—C8−177.10 (17)C17—C18—C19—C24−7.9 (3)
C1—C2—C7—C80.4 (3)C24—C19—C20—C210.7 (3)
C3—C2—C7—C60.6 (3)C18—C19—C20—C21−179.2 (2)
C1—C2—C7—C6178.07 (17)C19—C20—C21—C22−1.1 (3)
C5—C6—C7—C8176.95 (19)C20—C21—C22—C230.5 (4)
C5—C6—C7—C2−0.6 (3)C21—C22—C23—C240.5 (4)
C2—C7—C8—C90.1 (3)C22—C23—C24—C19−0.9 (4)
C6—C7—C8—C9−177.53 (18)C20—C19—C24—C230.3 (3)
C7—C8—C9—N1−0.5 (3)C18—C19—C24—C23−179.8 (2)
C7—C8—C9—C10177.49 (17)C17—C16—C25—C30−43.5 (3)
C1—N1—C9—C80.6 (3)N2—C16—C25—C30137.8 (2)
C1—N1—C9—C10−177.64 (16)C17—C16—C25—C26136.1 (2)
C8—C9—C10—C15−158.10 (19)N2—C16—C25—C26−42.5 (3)
N1—C9—C10—C1520.0 (3)C30—C25—C26—C27−2.2 (3)
C8—C9—C10—C1121.3 (3)C16—C25—C26—C27178.2 (2)
N1—C9—C10—C11−160.58 (18)C25—C26—C27—C280.5 (4)
C15—C10—C11—C120.0 (3)C26—C27—C28—C291.2 (4)
C9—C10—C11—C12−179.4 (2)C27—C28—C29—C30−1.2 (4)
C10—C11—C12—C13−0.3 (4)C28—C29—C30—C25−0.5 (4)
C11—C12—C13—C140.6 (4)C26—C25—C30—C292.2 (3)
C11—C12—C13—Cl1−178.40 (18)C16—C25—C30—C29−178.2 (2)
C12—C13—C14—C15−0.5 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5160).

References

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