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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o401.
Published online 2009 January 28. doi:  10.1107/S1600536809002797
PMCID: PMC2968172

2-{2-[3-(1H-Benzimidazol-2-yl)quinolin-2-yl­oxy]eth­oxy}ethanol

Abstract

In the title compound, C20H19N3O3, the inter­planar angle between the benzimidazole unit and the quinoline unit is 25.1 (2)°. Two different hydrogen bonds involving the hydr­oxy group and the imidazole unit are present. An intra­molecular N—H(...)O hydrogen bond links the hydr­oxy group of the side chain with the imidazole unit, forming a 12-membered ring, and an inter­molecular O—H(...)N hydrogen bond links the mol­ecules, forming chains in the crystallographic b direction.

Related literature

A closely related structure is reported in the previous paper, see: Rominger et al. (2009 [triangle]). An analogous pyridine compound is essentially flat (Kim et al., 2005 [triangle]).

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Object name is e-65-0o401-scheme1.jpg

Experimental

Crystal data

  • C20H19N3O3
  • M r = 349.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o401-efi1.jpg
  • a = 11.9478 (2) Å
  • b = 13.1338 (1) Å
  • c = 12.4031 (2) Å
  • β = 118.744 (1)°
  • V = 1706.47 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 200 (2) K
  • 0.43 × 0.28 × 0.18 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008b [triangle]) T min = 0.960, T max = 0.983
  • 16400 measured reflections
  • 3920 independent reflections
  • 2890 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.112
  • S = 1.02
  • 3920 reflections
  • 243 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008a [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002797/fj2184sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002797/fj2184Isup2.hkl

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

supplementary crystallographic information

Refinement

For all hydrogen atoms bond to a carbon atom the positions were calculated according to geometrical criteria. During the refinement the hydrogen atoms were allowed to shift with the preceding carbon atoms. The isotropic displacement parameters were set as 1.2 times the equivalent isotropic displacement parameters of the preceding carbon atoms. The positions of two hydrogen atoms of the heteroatoms were refined isotropically.

Figures

Fig. 1.
Thermal ellipsoid representation of the title compound with the intramolecular hydrogen bond indicated as dashed line. Displacement ellipsoids were plotted at 50% probability level.
Fig. 2.
Ball and stick representation of the hydrogen bond connected chain along the b direction. Hydrogen atoms not involved in hydrogen bonds (dashed lines) have been omitted.
Fig. 3.
Enhanced figure of the title compound with displacement ellipsoids plotted at 50% probability level.

Crystal data

C20H19N3O3F(000) = 736
Mr = 349.38Dx = 1.360 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7839 reflections
a = 11.9478 (2) Åθ = 1.9–27.5°
b = 13.1338 (1) ŵ = 0.09 mm1
c = 12.4031 (2) ÅT = 200 K
β = 118.744 (1)°Polyhedron, colourless
V = 1706.47 (4) Å30.43 × 0.28 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer3920 independent reflections
Radiation source: fine-focus sealed tube2890 reflections with I > 2σ(I)
graphiteRint = 0.051
ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b)h = −15→15
Tmin = 0.960, Tmax = 0.983k = −16→17
16400 measured reflectionsl = −16→16

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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0424P)2 + 0.5312P] where P = (Fo2 + 2Fc2)/3
3920 reflections(Δ/σ)max = 0.001
243 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.18 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

xyzUiso*/Ueq
N10.88443 (12)0.06208 (10)0.82383 (11)0.0329 (3)
C20.76960 (14)0.02903 (11)0.79014 (13)0.0292 (3)
C30.70017 (13)0.04708 (11)0.85560 (13)0.0280 (3)
C40.76217 (14)0.10173 (11)0.96231 (13)0.0296 (3)
H40.72030.11491.00940.036*
C50.88674 (14)0.13885 (11)1.00364 (13)0.0313 (3)
C60.95367 (16)0.19686 (13)1.11232 (15)0.0390 (4)
H60.91410.21291.16080.047*
C71.07435 (17)0.22987 (14)1.14778 (16)0.0453 (4)
H71.11920.26791.22160.054*
C81.13282 (17)0.20803 (14)1.07591 (17)0.0452 (4)
H81.21710.23151.10150.054*
C91.06998 (16)0.15334 (13)0.96934 (16)0.0401 (4)
H91.11050.13960.92120.048*
C100.94551 (14)0.11733 (11)0.93079 (14)0.0315 (3)
C120.56784 (13)0.01642 (11)0.81376 (13)0.0276 (3)
N130.49537 (12)0.06596 (9)0.85027 (11)0.0306 (3)
N140.50501 (12)−0.06326 (9)0.73809 (11)0.0296 (3)
H140.5367 (18)−0.1089 (15)0.7031 (17)0.053 (5)*
C210.37911 (14)0.01587 (11)0.79551 (13)0.0300 (3)
C220.26652 (15)0.03860 (13)0.79847 (15)0.0376 (4)
H220.26270.09360.84630.045*
C230.16163 (16)−0.02100 (14)0.73012 (16)0.0427 (4)
H230.0837−0.00650.73020.051*
C240.16696 (16)−0.10276 (14)0.66025 (17)0.0442 (4)
H240.0926−0.14270.61430.053*
C250.27764 (16)−0.12678 (13)0.65644 (15)0.0395 (4)
H250.2813−0.18250.60930.047*
C260.38342 (14)−0.06551 (11)0.72491 (13)0.0296 (3)
O310.70752 (10)−0.02559 (8)0.68516 (9)0.0339 (3)
C320.77582 (16)−0.04159 (13)0.61680 (14)0.0381 (4)
H32A0.8550−0.08080.66690.046*
H32B0.79930.02460.59510.046*
C330.68995 (17)−0.09925 (12)0.50313 (14)0.0396 (4)
H33A0.6050−0.06620.46150.048*
H33B0.7258−0.09880.44590.048*
O340.67706 (11)−0.20130 (8)0.53374 (10)0.0383 (3)
C350.56108 (17)−0.24765 (13)0.44759 (15)0.0427 (4)
H35A0.5703−0.32250.45630.051*
H35B0.5436−0.22980.36340.051*
C360.44979 (17)−0.21515 (14)0.46430 (17)0.0470 (4)
H36A0.4319−0.14220.44290.056*
H36B0.3732−0.25440.40740.056*
O370.47303 (13)−0.23023 (9)0.58596 (12)0.0464 (3)
H370.486 (2)−0.300 (2)0.604 (2)0.077 (7)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0349 (7)0.0330 (7)0.0346 (7)0.0019 (5)0.0197 (6)0.0033 (5)
C20.0315 (8)0.0271 (7)0.0299 (7)0.0032 (6)0.0157 (6)0.0034 (6)
C30.0296 (8)0.0261 (7)0.0301 (7)0.0030 (6)0.0158 (6)0.0042 (6)
C40.0307 (8)0.0295 (8)0.0315 (7)0.0029 (6)0.0173 (6)0.0029 (6)
C50.0325 (8)0.0282 (8)0.0320 (8)0.0028 (6)0.0145 (6)0.0048 (6)
C60.0402 (9)0.0388 (9)0.0379 (9)−0.0041 (7)0.0187 (7)−0.0019 (7)
C70.0440 (10)0.0421 (10)0.0424 (9)−0.0114 (8)0.0148 (8)−0.0034 (8)
C80.0362 (9)0.0430 (10)0.0527 (11)−0.0087 (8)0.0183 (8)0.0033 (8)
C90.0367 (9)0.0393 (9)0.0490 (10)−0.0004 (7)0.0243 (8)0.0067 (8)
C100.0312 (8)0.0280 (8)0.0354 (8)0.0025 (6)0.0160 (7)0.0058 (6)
C120.0308 (8)0.0264 (7)0.0261 (7)0.0022 (6)0.0142 (6)0.0038 (6)
N130.0304 (7)0.0323 (7)0.0318 (6)−0.0010 (5)0.0170 (5)−0.0026 (5)
N140.0334 (7)0.0249 (6)0.0337 (7)0.0006 (5)0.0187 (6)−0.0003 (5)
C210.0309 (8)0.0309 (8)0.0289 (7)−0.0010 (6)0.0150 (6)0.0021 (6)
C220.0351 (9)0.0420 (9)0.0395 (8)0.0011 (7)0.0210 (7)−0.0023 (7)
C230.0332 (9)0.0493 (10)0.0499 (10)−0.0028 (8)0.0235 (8)0.0006 (8)
C240.0368 (9)0.0440 (10)0.0502 (10)−0.0104 (8)0.0196 (8)−0.0047 (8)
C250.0434 (9)0.0322 (8)0.0438 (9)−0.0060 (7)0.0217 (8)−0.0053 (7)
C260.0322 (8)0.0275 (7)0.0310 (7)0.0004 (6)0.0167 (6)0.0041 (6)
O310.0359 (6)0.0396 (6)0.0318 (5)0.0000 (5)0.0207 (5)−0.0043 (5)
C320.0433 (9)0.0443 (9)0.0367 (8)0.0026 (7)0.0272 (7)0.0004 (7)
C330.0553 (10)0.0382 (9)0.0331 (8)0.0045 (8)0.0274 (8)0.0049 (7)
O340.0460 (7)0.0355 (6)0.0343 (6)0.0061 (5)0.0199 (5)0.0039 (5)
C350.0560 (11)0.0388 (9)0.0333 (8)0.0006 (8)0.0214 (8)−0.0013 (7)
C360.0478 (10)0.0397 (10)0.0505 (11)0.0007 (8)0.0213 (9)0.0065 (8)
O370.0656 (8)0.0295 (6)0.0596 (8)−0.0021 (6)0.0425 (7)−0.0045 (6)

Geometric parameters (Å, °)

N1—C21.3015 (19)C21—C261.398 (2)
N1—C101.374 (2)C22—C231.371 (2)
C2—O311.3532 (17)C22—H220.9500
C2—C31.432 (2)C23—C241.400 (3)
C3—C41.368 (2)C23—H230.9500
C3—C121.464 (2)C24—C251.382 (2)
C4—C51.408 (2)C24—H240.9500
C4—H40.9500C25—C261.391 (2)
C5—C101.414 (2)C25—H250.9500
C5—C61.414 (2)O31—C321.4472 (18)
C6—C71.360 (2)C32—C331.491 (2)
C6—H60.9500C32—H32A0.9900
C7—C81.401 (3)C32—H32B0.9900
C7—H70.9500C33—O341.4215 (19)
C8—C91.368 (2)C33—H33A0.9900
C8—H80.9500C33—H33B0.9900
C9—C101.407 (2)O34—C351.417 (2)
C9—H90.9500C35—C361.503 (3)
C12—N131.3248 (18)C35—H35A0.9900
C12—N141.3646 (19)C35—H35B0.9900
N13—C211.3843 (19)C36—O371.411 (2)
N14—C261.3818 (19)C36—H36A0.9900
N14—H140.92 (2)C36—H36B0.9900
C21—C221.396 (2)O37—H370.94 (3)
C2—N1—C10118.33 (13)C21—C22—H22121.1
N1—C2—O31119.41 (13)C22—C23—C24121.35 (16)
N1—C2—C3124.84 (14)C22—C23—H23119.3
O31—C2—C3115.75 (13)C24—C23—H23119.3
C4—C3—C2116.32 (13)C25—C24—C23121.67 (16)
C4—C3—C12118.51 (13)C25—C24—H24119.2
C2—C3—C12125.09 (13)C23—C24—H24119.2
C3—C4—C5121.31 (14)C24—C25—C26116.78 (15)
C3—C4—H4119.3C24—C25—H25121.6
C5—C4—H4119.3C26—C25—H25121.6
C4—C5—C10117.46 (14)N14—C26—C25132.82 (14)
C4—C5—C6123.21 (14)N14—C26—C21105.24 (13)
C10—C5—C6119.33 (14)C25—C26—C21121.90 (14)
C7—C6—C5120.36 (16)C2—O31—C32115.99 (12)
C7—C6—H6119.8O31—C32—C33107.60 (13)
C5—C6—H6119.8O31—C32—H32A110.2
C6—C7—C8120.28 (16)C33—C32—H32A110.2
C6—C7—H7119.9O31—C32—H32B110.2
C8—C7—H7119.9C33—C32—H32B110.2
C9—C8—C7120.81 (16)H32A—C32—H32B108.5
C9—C8—H8119.6O34—C33—C32109.88 (13)
C7—C8—H8119.6O34—C33—H33A109.7
C8—C9—C10120.26 (16)C32—C33—H33A109.7
C8—C9—H9119.9O34—C33—H33B109.7
C10—C9—H9119.9C32—C33—H33B109.7
N1—C10—C9119.30 (14)H33A—C33—H33B108.2
N1—C10—C5121.74 (13)C35—O34—C33113.32 (12)
C9—C10—C5118.95 (15)O34—C35—C36112.53 (14)
N13—C12—N14112.21 (13)O34—C35—H35A109.1
N13—C12—C3121.05 (13)C36—C35—H35A109.1
N14—C12—C3126.73 (13)O34—C35—H35B109.1
C12—N13—C21105.40 (12)C36—C35—H35B109.1
C12—N14—C26107.28 (12)H35A—C35—H35B107.8
C12—N14—H14127.4 (12)O37—C36—C35112.06 (15)
C26—N14—H14125.3 (12)O37—C36—H36A109.2
N13—C21—C22129.64 (14)C35—C36—H36A109.2
N13—C21—C26109.88 (13)O37—C36—H36B109.2
C22—C21—C26120.41 (14)C35—C36—H36B109.2
C23—C22—C21117.88 (15)H36A—C36—H36B107.9
C23—C22—H22121.1C36—O37—H37108.8 (14)
C10—N1—C2—O31−179.98 (13)N14—C12—N13—C210.02 (16)
C10—N1—C2—C30.9 (2)C3—C12—N13—C21−178.94 (12)
N1—C2—C3—C4−1.2 (2)N13—C12—N14—C26−0.11 (16)
O31—C2—C3—C4179.63 (13)C3—C12—N14—C26178.78 (13)
N1—C2—C3—C12175.39 (14)C12—N13—C21—C22−176.95 (16)
O31—C2—C3—C12−3.7 (2)C12—N13—C21—C260.07 (16)
C2—C3—C4—C50.8 (2)N13—C21—C22—C23176.58 (15)
C12—C3—C4—C5−176.08 (13)C26—C21—C22—C23−0.2 (2)
C3—C4—C5—C10−0.1 (2)C21—C22—C23—C240.6 (3)
C3—C4—C5—C6179.06 (14)C22—C23—C24—C25−0.3 (3)
C4—C5—C6—C7179.50 (15)C23—C24—C25—C26−0.3 (3)
C10—C5—C6—C7−1.3 (2)C12—N14—C26—C25177.47 (16)
C5—C6—C7—C81.0 (3)C12—N14—C26—C210.15 (15)
C6—C7—C8—C90.0 (3)C24—C25—C26—N14−176.25 (16)
C7—C8—C9—C10−0.6 (3)C24—C25—C26—C210.7 (2)
C2—N1—C10—C9179.66 (14)N13—C21—C26—N14−0.14 (16)
C2—N1—C10—C5−0.2 (2)C22—C21—C26—N14177.20 (13)
C8—C9—C10—N1−179.64 (15)N13—C21—C26—C25−177.82 (14)
C8—C9—C10—C50.2 (2)C22—C21—C26—C25−0.5 (2)
C4—C5—C10—N1−0.2 (2)N1—C2—O31—C32−0.87 (19)
C6—C5—C10—N1−179.44 (14)C3—C2—O31—C32178.30 (13)
C4—C5—C10—C9179.96 (14)C2—O31—C32—C33−177.84 (12)
C6—C5—C10—C90.7 (2)O31—C32—C33—O34−71.36 (16)
C4—C3—C12—N1322.5 (2)C32—C33—O34—C35153.87 (13)
C2—C3—C12—N13−154.07 (14)C33—O34—C35—C36−78.72 (17)
C4—C3—C12—N14−156.31 (14)O34—C35—C36—O37−53.58 (19)
C2—C3—C12—N1427.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N14—H14···O370.92 (2)2.04 (2)2.797 (2)138.3 (19)
O37—H37···N13i0.94 (3)1.83 (3)2.765 (2)175 (2)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2184).

References

  • Kim, H. N., Lee, H. K. & Lee, S. W. (2005). Bull. Korean Chem. Soc.26, 892–898.
  • Rominger, F., Malathi, M., Mohan, P. S., Ramamurthi Dondeti, T. & Hashmi, A. S. K. (2009). Acta Cryst. E65, o400.
  • Sheldrick, G. M. (2008a). Acta Cryst. A64, 112–122. [PubMed]
  • Sheldrick, G. M. (2008b). SADABS University of Göttingen, Germany.
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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