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COMMUNICATIONS
ISSN: 2056-9890

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

aChemistry Division, School of Science and Humanities, VIT University, Vellore 632014, Tamil Nadu, India, bChemistry Division, School of Advanced Sciences, VIT University, Vellore 632014, Tamil Nadu, India, cSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560012, Karnataka, India, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 28 December 2009; accepted 30 December 2009; online 16 January 2010)

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[Broadhurst, M. J., Johnson, W. H. & Walter, D. S. (2001). US Patent No. 6235787.]).

[Scheme 1]

Experimental

Crystal data
  • C30H20ClN3

  • Mr = 457.94

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.963, Tmax = 0.993

  • 17230 measured reflections

  • 4392 independent reflections

  • 2890 reflections with I > 2σ(I)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 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[Bruker (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). publCIF. In preparation.]).

Supporting information


Related literature top

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

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C30H20ClN3 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
1-[3-(4-Chlorophenyl)isoquinolin-1-yl]-3,5-diphenyl-1H-pyrazole top
Crystal data top
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 top
Bruker SMART area-detector
diffractometer
4392 independent reflections
Radiation source: fine-focus sealed tube2890 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
ϕ and ω scansθmax = 25.7°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2926
Tmin = 0.963, Tmax = 0.993k = 1414
17230 measured reflectionsl = 1010
Refinement top
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 = 1.02 w = 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
Crystal data top
C30H20ClN3V = 2312.6 (3) Å3
Mr = 457.94Z = 4
Monoclinic, P21/cMo Kα radiation
a = 23.7864 (15) ŵ = 0.19 mm1
b = 11.7101 (8) ÅT = 290 K
c = 8.3602 (5) Å0.20 × 0.16 × 0.04 mm
β = 96.738 (1)°
Data collection top
Bruker SMART area-detector
diffractometer
4392 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2890 reflections with I > 2σ(I)
Tmin = 0.963, Tmax = 0.993Rint = 0.039
17230 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.02Δρmax = 0.16 e Å3
4392 reflectionsΔρmin = 0.19 e Å3
307 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H210.01370.21290.90440.090*
C220.00553 (11)0.0715 (2)0.7861 (3)0.0740 (7)
H220.02480.02750.81130.089*
C230.04403 (11)0.02741 (19)0.6942 (3)0.0742 (7)
H230.03980.04700.65580.089*
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) top
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, º) top
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—C180.4 (2)Cl1—C13—C14—C15178.42 (18)
C1—N2—N3—C18172.66 (16)C13—C14—C15—C100.3 (3)
C9—N1—C1—C20.1 (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—N157.8 (2)C1—N2—C16—C17172.00 (18)
N3—N2—C1—C269.1 (2)N3—N2—C16—C25179.40 (17)
C16—N2—C1—C2119.8 (2)C1—N2—C16—C259.0 (3)
N1—C1—C2—C3176.97 (18)N2—C16—C17—C180.3 (2)
N2—C1—C2—C30.4 (3)C25—C16—C17—C18179.16 (19)
N1—C1—C2—C70.3 (3)N2—N3—C18—C170.1 (2)
N2—C1—C2—C7177.68 (16)N2—N3—C18—C19179.74 (16)
C1—C2—C3—C4177.35 (18)C16—C17—C18—N30.1 (2)
C7—C2—C3—C40.1 (3)C16—C17—C18—C19179.44 (18)
C2—C3—C4—C50.4 (3)N3—C18—C19—C207.5 (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—C8177.10 (17)C17—C18—C19—C247.9 (3)
C1—C2—C7—C80.4 (3)C24—C19—C20—C210.7 (3)
C3—C2—C7—C60.6 (3)C18—C19—C20—C21179.2 (2)
C1—C2—C7—C6178.07 (17)C19—C20—C21—C221.1 (3)
C5—C6—C7—C8176.95 (19)C20—C21—C22—C230.5 (4)
C5—C6—C7—C20.6 (3)C21—C22—C23—C240.5 (4)
C2—C7—C8—C90.1 (3)C22—C23—C24—C190.9 (4)
C6—C7—C8—C9177.53 (18)C20—C19—C24—C230.3 (3)
C7—C8—C9—N10.5 (3)C18—C19—C24—C23179.8 (2)
C7—C8—C9—C10177.49 (17)C17—C16—C25—C3043.5 (3)
C1—N1—C9—C80.6 (3)N2—C16—C25—C30137.8 (2)
C1—N1—C9—C10177.64 (16)C17—C16—C25—C26136.1 (2)
C8—C9—C10—C15158.10 (19)N2—C16—C25—C2642.5 (3)
N1—C9—C10—C1520.0 (3)C30—C25—C26—C272.2 (3)
C8—C9—C10—C1121.3 (3)C16—C25—C26—C27178.2 (2)
N1—C9—C10—C11160.58 (18)C25—C26—C27—C280.5 (4)
C15—C10—C11—C120.0 (3)C26—C27—C28—C291.2 (4)
C9—C10—C11—C12179.4 (2)C27—C28—C29—C301.2 (4)
C10—C11—C12—C130.3 (4)C28—C29—C30—C250.5 (4)
C11—C12—C13—C140.6 (4)C26—C25—C30—C292.2 (3)
C11—C12—C13—Cl1178.40 (18)C16—C25—C30—C29178.2 (2)
C12—C13—C14—C150.5 (4)

Experimental details

Crystal data
Chemical formulaC30H20ClN3
Mr457.94
Crystal system, space groupMonoclinic, P21/c
Temperature (K)290
a, b, c (Å)23.7864 (15), 11.7101 (8), 8.3602 (5)
β (°) 96.738 (1)
V3)2312.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.20 × 0.16 × 0.04
Data collection
DiffractometerBruker SMART area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.963, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
17230, 4392, 2890
Rint0.039
(sin θ/λ)max1)0.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.126, 1.02
No. of reflections4392
No. of parameters307
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.19

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

 

Acknowledgements

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.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationBroadhurst, M. J., Johnson, W. H. & Walter, D. S. (2001). US Patent No. 6235787.
First citationBruker (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2010). publCIF. In preparation.

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