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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2493.
Published online 2009 September 19. doi:  10.1107/S1600536809037131
PMCID: PMC2970475

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

Abstract

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 [triangle]).

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Object name is e-65-o2493-scheme1.jpg

Experimental

Crystal data

  • C24H26N4O4
  • M r = 434.49
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2493-efi1.jpg
  • 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)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 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 [triangle]); cell refinement: KappaCCD Server Software; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997 [triangle]); 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, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037131/tk2541sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037131/tk2541Isup2.hkl

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

Acknowledgments

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.

supplementary crystallographic information

Experimental

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

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).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C24H26N4O4 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

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

Nonius KappaCCD diffractometer3705 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
graphiteθmax = 26.4°, θmin = 1.6°
[var phi] scansh = −16→16
4728 measured reflectionsk = 0→19
4559 independent reflectionsl = 0→13

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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176H-atom parameters constrained
S = 1.16w = 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

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

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)
H130.73890.5424−0.03560.078*
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)
H200.26980.7715−0.12310.072*
C210.12347 (19)0.76134 (16)−0.2191 (2)0.0749 (6)
H210.12730.8037−0.27660.090*
C220.0333 (2)0.71854 (18)−0.2258 (2)0.0863 (8)
H22−0.02390.7314−0.28820.104*
C230.02757 (19)0.65628 (19)−0.1396 (3)0.0910 (8)
H23−0.03390.6277−0.14340.109*
C240.11280 (16)0.63617 (15)−0.0476 (2)0.0723 (6)
H240.10830.59420.01020.087*

Atomic displacement parameters (Å2)

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, °)

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—C18−177.89 (16)N1—C10—C15—C14−179.58 (16)
C9—N1—C1—C294.0 (2)C11—C10—C15—N2179.97 (16)
C10—N1—C1—C2−78.1 (3)N1—C10—C15—N2−0.06 (18)
C3—O1—C2—C1−160.4 (2)C9—N2—C15—C14179.20 (18)
N1—C1—C2—O182.7 (2)C16—N2—C15—C14−0.8 (3)
C2—O1—C3—C4101.9 (2)C9—N2—C15—C10−0.24 (18)
C5—O2—C4—C3164.8 (2)C16—N2—C15—C10179.74 (15)
O1—C3—C4—O2−73.7 (2)N4—N3—C16—C17−1.25 (19)
C4—O2—C5—C6170.39 (18)C8—N3—C16—C17177.59 (18)
C7—O3—C6—C5−169.59 (19)N4—N3—C16—N2178.75 (15)
O2—C5—C6—O364.1 (2)C8—N3—C16—N2−2.4 (3)
C6—O3—C7—C8172.95 (17)C9—N2—C16—N3−58.0 (2)
N4—N3—C8—C797.73 (19)C15—N2—C16—N3122.04 (19)
C16—N3—C8—C7−81.0 (2)C9—N2—C16—C17122.0 (2)
O3—C7—C8—N373.3 (2)C15—N2—C16—C17−58.0 (3)
C10—N1—C9—O4179.75 (19)N3—C16—C17—C180.86 (18)
C1—N1—C9—O46.3 (3)N2—C16—C17—C18−179.14 (16)
C10—N1—C9—N2−0.49 (19)N3—N4—C18—C17−0.51 (19)
C1—N1—C9—N2−173.91 (16)N3—N4—C18—C19−178.65 (15)
C16—N2—C9—O40.2 (3)C16—C17—C18—N4−0.21 (19)
C15—N2—C9—O4−179.79 (19)C16—C17—C18—C19177.74 (16)
C16—N2—C9—N1−179.53 (15)N4—C18—C19—C20164.40 (17)
C15—N2—C9—N10.45 (19)C17—C18—C19—C20−13.4 (3)
C9—N1—C10—C11−179.68 (18)N4—C18—C19—C24−15.2 (3)
C1—N1—C10—C11−6.8 (3)C17—C18—C19—C24166.97 (19)
C9—N1—C10—C150.4 (2)C24—C19—C20—C21−1.3 (3)
C1—N1—C10—C15173.20 (18)C18—C19—C20—C21179.05 (18)
C15—C10—C11—C12−0.2 (3)C19—C20—C21—C220.4 (3)
N1—C10—C11—C12179.87 (19)C20—C21—C22—C230.7 (4)
C10—C11—C12—C13−0.4 (3)C21—C22—C23—C24−0.9 (4)
C11—C12—C13—C140.7 (3)C22—C23—C24—C190.0 (4)
C12—C13—C14—C15−0.4 (3)C20—C19—C24—C231.1 (3)
C13—C14—C15—C10−0.2 (3)C18—C19—C24—C23−179.2 (2)
C13—C14—C15—N2−179.54 (18)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2541).

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