organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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4-Phenyl-9,12,15-trioxa-1,5,6,18-tetra­aza­tetra­cyclo­[16.6.1.02,6.019,24]penta­conta-2,4,19,21,23-pentaen-25-one

aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, bInstitute of Nanomaterials and Nanotechnology, Avenue de l'Armée Royale, Madinat El Irfane, 10100 Rabat, Morocco, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 14 September 2009; accepted 14 September 2009; online 19 September 2009)

The title compound, C24H26N4O4, is a diaza-crown ether encompassing linked phenylpyrazolyl and benzimidazole units that contribute five atoms to the 16-atom ring. The two planar phenylpyrazolyl and benzimidazole units are aligned at an angle of 66.4 (1)°. The carbonyl O atom of the benzimidazole unit is directed away from the middle of the ring.

Related literature

For the selective recognition of sodium and potassium cyanide by diaza-crown ethers, see: Liu et al. (2005[Liu, H., Shao, X.-B., Jia, M.-X., Jiang, X.-K., Li, Z.-T. & Chen, G.-J. (2005). Tetrahedron, 61, 8095-8100.]).

[Scheme 1]

Experimental

Crystal data
  • C24H26N4O4

  • Mr = 434.49

  • Monoclinic, P 21 /c

  • a = 13.348 (1) Å

  • b = 15.785 (1) Å

  • c = 11.007 (1) Å

  • β = 102.681 (1)°

  • V = 2262.6 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.30 × 0.30 × 0.20 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: none

  • 4728 measured reflections

  • 4559 independent reflections

  • 3705 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.176

  • S = 1.16

  • 4559 reflections

  • 289 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.30 e Å−3

Data collection: KappaCCD Server Software (Nonius, 1998[Nonius (1998). KappaCCD Server Software. Nonius BV, Delft, The Netherlands.]); cell refinement: KappaCCD Server Software; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); 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, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For the selective recognition of sodium and potassium cyanide by diaza-crown ethers, see: Liu et al. (2005).

Experimental top

1-(3-Phenylpyrazolyl)benzimidazol-2-one (1 g, 4.5 mmol), dichlorotetraethyleneglycol (0.31 ml, 5.0 mmol), potassium carbonate (0.7 g, 5.0 mmol) and a catalytic quantity of tetra-n-butylammonium bromide were stirred in N,N-dimethylformamide (60 ml) in an oil bath heated to 353–363 K for 24 h. The insoluble salts were filtered off and the solvent removed in vacuum. The residue was separated by chromatography on silica gel with a hexane:ethyl acetate (7:3) solvent system. Evaporation of the solvent gave the compound as colorless crystals in 25% yield; m.p. 402–404 K.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1998); cell refinement: KappaCCD Server Software (Nonius, 1998); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C24H26N4O4 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
4-Phenyl-9,12,15-trioxa-1,5,6,18- tetraazatetracyclo[16.6.1.02,6.019,24]pentaconta-2,4,19,21,23- pentaen-25-one top
Crystal data top
C24H26N4O4F(000) = 920
Mr = 434.49Dx = 1.276 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4728 reflections
a = 13.348 (1) Åθ = 1.3–26.4°
b = 15.785 (1) ŵ = 0.09 mm1
c = 11.007 (1) ÅT = 293 K
β = 102.681 (1)°Prism, colorless
V = 2262.6 (3) Å30.30 × 0.30 × 0.20 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
3705 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
Graphite monochromatorθmax = 26.4°, θmin = 1.6°
ϕ scansh = 1616
4728 measured reflectionsk = 019
4559 independent reflectionsl = 013
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176H-atom parameters constrained
S = 1.16 w = 1/[σ2(Fo2) + (0.0966P)2 + 0.3451P]
where P = (Fo2 + 2Fc2)/3
4559 reflections(Δ/σ)max < 0.001
289 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C24H26N4O4V = 2262.6 (3) Å3
Mr = 434.49Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.348 (1) ŵ = 0.09 mm1
b = 15.785 (1) ÅT = 293 K
c = 11.007 (1) Å0.30 × 0.30 × 0.20 mm
β = 102.681 (1)°
Data collection top
Nonius KappaCCD
diffractometer
3705 reflections with I > 2σ(I)
4728 measured reflectionsRint = 0.038
4559 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.176H-atom parameters constrained
S = 1.16Δρmax = 0.34 e Å3
4559 reflectionsΔρmin = 0.30 e Å3
289 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.87698 (11)0.57891 (11)0.53630 (16)0.0794 (5)
O20.74157 (12)0.43571 (10)0.44390 (16)0.0745 (4)
O30.53984 (12)0.47052 (9)0.31375 (15)0.0699 (4)
O40.54645 (11)0.71208 (10)0.41785 (13)0.0682 (4)
N10.70082 (11)0.67744 (10)0.36647 (14)0.0524 (4)
N20.55695 (10)0.65098 (9)0.22803 (13)0.0449 (3)
N30.38396 (11)0.60439 (10)0.22449 (13)0.0499 (4)
N40.28762 (10)0.61095 (10)0.15421 (14)0.0520 (4)
C10.76670 (16)0.69810 (14)0.4862 (2)0.0661 (5)
H1A0.73220.73920.52820.079*
H1B0.82930.72400.47280.079*
C20.79396 (16)0.62171 (18)0.5685 (2)0.0753 (6)
H2A0.81250.63920.65500.090*
H2B0.73520.58410.55830.090*
C30.88970 (18)0.4930 (2)0.5761 (3)0.0900 (8)
H3A0.85340.48340.64220.108*
H3B0.96200.48160.60910.108*
C40.84994 (19)0.43449 (18)0.4718 (3)0.0905 (9)
H4A0.87490.45160.39910.109*
H4B0.87430.37750.49430.109*
C50.6978 (2)0.39909 (15)0.3267 (2)0.0809 (7)
H5A0.72860.34410.31980.097*
H5B0.71120.43500.26050.097*
C60.5855 (2)0.38942 (13)0.3138 (2)0.0767 (6)
H6A0.55610.36020.23670.092*
H6B0.57200.35600.38240.092*
C70.43698 (16)0.46653 (14)0.32369 (19)0.0647 (5)
H7A0.43110.43220.39490.078*
H7B0.39540.44090.24940.078*
C80.40064 (15)0.55449 (14)0.33892 (17)0.0605 (5)
H8A0.33690.55170.36730.073*
H8B0.45090.58310.40270.073*
C90.59594 (13)0.68361 (11)0.34668 (17)0.0499 (4)
C100.72822 (13)0.64095 (10)0.26302 (17)0.0471 (4)
C110.82330 (14)0.62168 (12)0.2396 (2)0.0590 (5)
H110.88370.63290.29780.071*
C120.82438 (17)0.58505 (14)0.1261 (2)0.0685 (6)
H120.88710.57170.10740.082*
C130.73509 (17)0.56767 (14)0.0395 (2)0.0652 (5)
H130.73890.54240.03560.078*
C140.63960 (15)0.58741 (12)0.06293 (17)0.0547 (4)
H140.57920.57610.00470.066*
C150.63804 (12)0.62421 (10)0.17555 (16)0.0441 (4)
C160.45233 (12)0.64657 (10)0.17250 (15)0.0438 (4)
C170.39923 (13)0.68079 (10)0.06243 (16)0.0461 (4)
H170.42530.71260.00530.055*
C180.29661 (13)0.65690 (10)0.05540 (15)0.0460 (4)
C190.20534 (13)0.67861 (11)0.04115 (16)0.0508 (4)
C200.20897 (16)0.74172 (13)0.12711 (18)0.0602 (5)
H200.26980.77150.12310.072*
C210.12347 (19)0.76134 (16)0.2191 (2)0.0749 (6)
H210.12730.80370.27660.090*
C220.0333 (2)0.71854 (18)0.2258 (2)0.0863 (8)
H220.02390.73140.28820.104*
C230.02757 (19)0.65628 (19)0.1396 (3)0.0910 (8)
H230.03390.62770.14340.109*
C240.11280 (16)0.63617 (15)0.0476 (2)0.0723 (6)
H240.10830.59420.01020.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0499 (8)0.0938 (11)0.0948 (11)0.0035 (7)0.0166 (7)0.0240 (9)
O20.0620 (9)0.0817 (10)0.0879 (11)0.0055 (7)0.0339 (8)0.0023 (8)
O30.0719 (10)0.0537 (8)0.0884 (11)0.0005 (6)0.0270 (8)0.0132 (7)
O40.0574 (8)0.0837 (10)0.0644 (8)0.0036 (7)0.0153 (6)0.0271 (7)
N10.0391 (8)0.0581 (9)0.0564 (9)0.0015 (6)0.0025 (6)0.0121 (7)
N20.0364 (7)0.0515 (8)0.0457 (7)0.0022 (5)0.0066 (5)0.0064 (6)
N30.0381 (7)0.0627 (9)0.0476 (8)0.0022 (6)0.0067 (6)0.0078 (6)
N40.0375 (7)0.0633 (9)0.0525 (8)0.0039 (6)0.0037 (6)0.0032 (7)
C10.0534 (11)0.0746 (13)0.0643 (12)0.0117 (9)0.0002 (9)0.0193 (10)
C20.0507 (11)0.1098 (18)0.0612 (12)0.0070 (11)0.0032 (9)0.0040 (12)
C30.0520 (12)0.110 (2)0.106 (2)0.0051 (13)0.0119 (12)0.0449 (17)
C40.0650 (14)0.0863 (17)0.133 (2)0.0198 (12)0.0494 (15)0.0357 (17)
C50.105 (2)0.0658 (13)0.0814 (16)0.0234 (12)0.0423 (14)0.0053 (12)
C60.1036 (19)0.0526 (11)0.0731 (14)0.0036 (11)0.0177 (13)0.0005 (10)
C70.0582 (12)0.0722 (13)0.0589 (11)0.0143 (9)0.0027 (9)0.0201 (10)
C80.0509 (10)0.0840 (14)0.0463 (9)0.0043 (9)0.0101 (8)0.0145 (9)
C90.0461 (9)0.0509 (9)0.0516 (9)0.0000 (7)0.0082 (7)0.0095 (8)
C100.0423 (9)0.0435 (8)0.0556 (10)0.0006 (6)0.0107 (7)0.0002 (7)
C110.0424 (9)0.0630 (11)0.0724 (12)0.0028 (8)0.0143 (8)0.0057 (9)
C120.0590 (12)0.0738 (13)0.0806 (14)0.0150 (10)0.0328 (11)0.0071 (11)
C130.0731 (13)0.0671 (12)0.0615 (11)0.0087 (10)0.0280 (10)0.0040 (10)
C140.0588 (11)0.0551 (10)0.0507 (9)0.0019 (8)0.0133 (8)0.0033 (8)
C150.0431 (9)0.0399 (8)0.0509 (9)0.0011 (6)0.0140 (7)0.0008 (7)
C160.0385 (8)0.0468 (8)0.0457 (8)0.0022 (6)0.0083 (6)0.0028 (7)
C170.0469 (9)0.0439 (8)0.0473 (9)0.0019 (7)0.0099 (7)0.0013 (7)
C180.0443 (9)0.0443 (8)0.0469 (9)0.0001 (6)0.0046 (7)0.0029 (7)
C190.0495 (10)0.0497 (9)0.0496 (9)0.0060 (7)0.0030 (7)0.0080 (8)
C200.0595 (11)0.0609 (11)0.0555 (10)0.0093 (9)0.0029 (8)0.0008 (9)
C210.0790 (15)0.0770 (14)0.0611 (12)0.0232 (12)0.0009 (10)0.0070 (10)
C220.0712 (15)0.0955 (17)0.0761 (15)0.0222 (13)0.0190 (12)0.0039 (13)
C230.0541 (13)0.1033 (19)0.0994 (19)0.0065 (12)0.0181 (12)0.0013 (16)
C240.0528 (11)0.0753 (14)0.0789 (14)0.0048 (10)0.0071 (10)0.0058 (11)
Geometric parameters (Å, º) top
O1—C21.408 (3)C6—H6B0.9700
O1—C31.424 (3)C7—C81.492 (3)
O2—C41.411 (3)C7—H7A0.9700
O2—C51.418 (3)C7—H7B0.9700
O3—C71.402 (2)C8—H8A0.9700
O3—C61.418 (3)C8—H8B0.9700
O4—C91.216 (2)C10—C111.383 (2)
N1—C91.372 (2)C10—C151.392 (2)
N1—C101.395 (2)C11—C121.380 (3)
N1—C11.452 (2)C11—H110.9300
N2—C91.394 (2)C12—C131.380 (3)
N2—C161.398 (2)C12—H120.9300
N2—C151.399 (2)C13—C141.390 (3)
N3—N41.3513 (19)C13—H130.9300
N3—C161.354 (2)C14—C151.373 (3)
N3—C81.460 (2)C14—H140.9300
N4—C181.334 (2)C16—C171.373 (2)
C1—C21.504 (3)C17—C181.406 (2)
C1—H1A0.9700C17—H170.9300
C1—H1B0.9700C18—C191.471 (2)
C2—H2A0.9700C19—C201.382 (3)
C2—H2B0.9700C19—C241.393 (3)
C3—C41.478 (4)C20—C211.385 (3)
C3—H3A0.9700C20—H200.9300
C3—H3B0.9700C21—C221.368 (4)
C4—H4A0.9700C21—H210.9300
C4—H4B0.9700C22—C231.380 (4)
C5—C61.482 (4)C22—H220.9300
C5—H5A0.9700C23—C241.384 (3)
C5—H5B0.9700C23—H230.9300
C6—H6A0.9700C24—H240.9300
C2—O1—C3115.28 (18)N3—C8—C7113.37 (17)
C4—O2—C5113.0 (2)N3—C8—H8A108.9
C7—O3—C6112.79 (17)C7—C8—H8A108.9
C9—N1—C10109.93 (14)N3—C8—H8B108.9
C9—N1—C1121.44 (16)C7—C8—H8B108.9
C10—N1—C1128.23 (16)H8A—C8—H8B107.7
C9—N2—C16124.04 (14)O4—C9—N1127.12 (17)
C9—N2—C15109.56 (13)O4—C9—N2126.59 (16)
C16—N2—C15126.40 (14)N1—C9—N2106.29 (14)
N4—N3—C16111.43 (13)C11—C10—C15121.28 (17)
N4—N3—C8118.73 (14)C11—C10—N1131.19 (17)
C16—N3—C8129.83 (15)C15—C10—N1107.53 (14)
C18—N4—N3105.29 (13)C12—C11—C10116.95 (19)
N1—C1—C2112.63 (18)C12—C11—H11121.5
N1—C1—H1A109.1C10—C11—H11121.5
C2—C1—H1A109.1C11—C12—C13121.98 (18)
N1—C1—H1B109.1C11—C12—H12119.0
C2—C1—H1B109.1C13—C12—H12119.0
H1A—C1—H1B107.8C12—C13—C14121.01 (19)
O1—C2—C1109.45 (19)C12—C13—H13119.5
O1—C2—H2A109.8C14—C13—H13119.5
C1—C2—H2A109.8C15—C14—C13117.28 (18)
O1—C2—H2B109.8C15—C14—H14121.4
C1—C2—H2B109.8C13—C14—H14121.4
H2A—C2—H2B108.2C14—C15—C10121.50 (16)
O1—C3—C4110.9 (2)C14—C15—N2131.82 (16)
O1—C3—H3A109.4C10—C15—N2106.68 (14)
C4—C3—H3A109.4N3—C16—C17107.53 (14)
O1—C3—H3B109.4N3—C16—N2122.76 (15)
C4—C3—H3B109.5C17—C16—N2129.72 (15)
H3A—C3—H3B108.0C16—C17—C18104.54 (15)
O2—C4—C3109.7 (2)C16—C17—H17127.7
O2—C4—H4A109.7C18—C17—H17127.7
C3—C4—H4A109.7N4—C18—C17111.20 (15)
O2—C4—H4B109.7N4—C18—C19120.47 (16)
C3—C4—H4B109.7C17—C18—C19128.30 (17)
H4A—C4—H4B108.2C20—C19—C24118.42 (18)
O2—C5—C6109.61 (18)C20—C19—C18120.97 (17)
O2—C5—H5A109.7C24—C19—C18120.61 (18)
C6—C5—H5A109.7C19—C20—C21121.0 (2)
O2—C5—H5B109.7C19—C20—H20119.5
C6—C5—H5B109.7C21—C20—H20119.5
H5A—C5—H5B108.2C22—C21—C20120.2 (2)
O3—C6—C5109.42 (19)C22—C21—H21119.9
O3—C6—H6A109.8C20—C21—H21119.9
C5—C6—H6A109.8C21—C22—C23119.7 (2)
O3—C6—H6B109.8C21—C22—H22120.1
C5—C6—H6B109.8C23—C22—H22120.1
H6A—C6—H6B108.2C22—C23—C24120.4 (2)
O3—C7—C8108.36 (16)C22—C23—H23119.8
O3—C7—H7A110.0C24—C23—H23119.8
C8—C7—H7A110.0C23—C24—C19120.3 (2)
O3—C7—H7B110.0C23—C24—H24119.9
C8—C7—H7B110.0C19—C24—H24119.9
H7A—C7—H7B108.4
C16—N3—N4—C181.09 (19)C11—C10—C15—C140.5 (3)
C8—N3—N4—C18177.89 (16)N1—C10—C15—C14179.58 (16)
C9—N1—C1—C294.0 (2)C11—C10—C15—N2179.97 (16)
C10—N1—C1—C278.1 (3)N1—C10—C15—N20.06 (18)
C3—O1—C2—C1160.4 (2)C9—N2—C15—C14179.20 (18)
N1—C1—C2—O182.7 (2)C16—N2—C15—C140.8 (3)
C2—O1—C3—C4101.9 (2)C9—N2—C15—C100.24 (18)
C5—O2—C4—C3164.8 (2)C16—N2—C15—C10179.74 (15)
O1—C3—C4—O273.7 (2)N4—N3—C16—C171.25 (19)
C4—O2—C5—C6170.39 (18)C8—N3—C16—C17177.59 (18)
C7—O3—C6—C5169.59 (19)N4—N3—C16—N2178.75 (15)
O2—C5—C6—O364.1 (2)C8—N3—C16—N22.4 (3)
C6—O3—C7—C8172.95 (17)C9—N2—C16—N358.0 (2)
N4—N3—C8—C797.73 (19)C15—N2—C16—N3122.04 (19)
C16—N3—C8—C781.0 (2)C9—N2—C16—C17122.0 (2)
O3—C7—C8—N373.3 (2)C15—N2—C16—C1758.0 (3)
C10—N1—C9—O4179.75 (19)N3—C16—C17—C180.86 (18)
C1—N1—C9—O46.3 (3)N2—C16—C17—C18179.14 (16)
C10—N1—C9—N20.49 (19)N3—N4—C18—C170.51 (19)
C1—N1—C9—N2173.91 (16)N3—N4—C18—C19178.65 (15)
C16—N2—C9—O40.2 (3)C16—C17—C18—N40.21 (19)
C15—N2—C9—O4179.79 (19)C16—C17—C18—C19177.74 (16)
C16—N2—C9—N1179.53 (15)N4—C18—C19—C20164.40 (17)
C15—N2—C9—N10.45 (19)C17—C18—C19—C2013.4 (3)
C9—N1—C10—C11179.68 (18)N4—C18—C19—C2415.2 (3)
C1—N1—C10—C116.8 (3)C17—C18—C19—C24166.97 (19)
C9—N1—C10—C150.4 (2)C24—C19—C20—C211.3 (3)
C1—N1—C10—C15173.20 (18)C18—C19—C20—C21179.05 (18)
C15—C10—C11—C120.2 (3)C19—C20—C21—C220.4 (3)
N1—C10—C11—C12179.87 (19)C20—C21—C22—C230.7 (4)
C10—C11—C12—C130.4 (3)C21—C22—C23—C240.9 (4)
C11—C12—C13—C140.7 (3)C22—C23—C24—C190.0 (4)
C12—C13—C14—C150.4 (3)C20—C19—C24—C231.1 (3)
C13—C14—C15—C100.2 (3)C18—C19—C24—C23179.2 (2)
C13—C14—C15—N2179.54 (18)

Experimental details

Crystal data
Chemical formulaC24H26N4O4
Mr434.49
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.348 (1), 15.785 (1), 11.007 (1)
β (°) 102.681 (1)
V3)2262.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.30 × 0.20
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4728, 4559, 3705
Rint0.038
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.176, 1.16
No. of reflections4559
No. of parameters289
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.30

Computer programs: KappaCCD Server Software (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

We thank the Laboratoire de Cristallochimie de la Faculté des Sciences, Université Paul Cézanne Aix-Marseille III, for the diffraction measurements. The Université Mohammed V-Agdal and the University of Malaya are thanked for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationLiu, H., Shao, X.-B., Jia, M.-X., Jiang, X.-K., Li, Z.-T. & Chen, G.-J. (2005). Tetrahedron, 61, 8095–8100.  Web of Science CrossRef CAS Google Scholar
First citationNonius (1998). KappaCCD Server Software. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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