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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3192.
Published online 2009 November 25. doi:  10.1107/S1600536809048302
PMCID: PMC2971907

2-(4-Chloro­phen­yl)imidazo[1,2-a]pyridine-3-carbaldehyde

Abstract

The asymmetric unit of the title compound, C14H9ClN2O, contains two mol­ecules with dihedral angles of 33.52 (11) and 34.58 (11)° between their benzene rings and imidazole ring systems. In the crystal, C—H(...)N and C—H(...)O inter­actions are observed. The crystal examined was found to be a racemic twin.

Related literature

For the synthesis, see: Burkholder et al. (2001 [triangle]).

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Object name is e-65-o3192-scheme1.jpg

Experimental

Crystal data

  • C14H9ClN2O
  • M r = 256.68
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3192-efi1.jpg
  • a = 21.3367 (13) Å
  • b = 7.2391 (4) Å
  • c = 15.1748 (10) Å
  • V = 2343.9 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.31 mm−1
  • T = 293 K
  • 0.35 × 0.29 × 0.28 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2002 [triangle]) T min = 0.870, T max = 0.894
  • 12428 measured reflections
  • 4198 independent reflections
  • 3564 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.089
  • S = 1.03
  • 4198 reflections
  • 325 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.18 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1800 Friedel pairs
  • Flack parameter: 0.40 (5)

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048302/hb5204sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048302/hb5204Isup2.hkl

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

Acknowledgments

The authors thank Changchun University of Science and Technology for supporting this work.

supplementary crystallographic information

Experimental

To a solution of 2.0 mmol 2-(4-chlorophenyl)H-imidazo[1,2-a]pyridine (Burkholder et al., 2001) in DMF (10 ml) was added phosphoryl trichloride (2.2 mmol) in one portion at room temperature under stirring. The mixture was heated to 353 K and stirred for 5.0 h. After the intermediate was consumed (monitored by TLC), the reaction mixture was extracted, filtered and concentrated in vacuo. The pure product was obtained through silica gel chromatography, and yellow blocks of (I) were obtained by slow evaporation of an ethyl acetate/petroleum ether (1:1) solution at room temperature.

Refinement

All H atoms were generated geometrically and refined as riding atoms with C—H = 0.93Å and Uiso(H) = 1.2 Ueq(C).

Figures

Fig. 1.
Molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level for non-H atoms.

Crystal data

C14H9ClN2OF(000) = 1056
Mr = 256.68Dx = 1.455 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 4265 reflections
a = 21.3367 (13) Åθ = 1.9–26.0°
b = 7.2391 (4) ŵ = 0.31 mm1
c = 15.1748 (10) ÅT = 293 K
V = 2343.9 (2) Å3Block, yellow
Z = 80.35 × 0.29 × 0.28 mm

Data collection

Bruker APEX CCD diffractometer4198 independent reflections
Radiation source: fine-focus sealed tube3564 reflections with I > 2σ(I)
graphiteRint = 0.026
ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)h = −26→26
Tmin = 0.870, Tmax = 0.894k = −8→8
12428 measured reflectionsl = −15→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.089w = 1/[σ2(Fo2) + (0.0461P)2 + 0.2155P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4198 reflectionsΔρmax = 0.22 e Å3
325 parametersΔρmin = −0.18 e Å3
1 restraintAbsolute structure: Flack (1983), 1800 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.40 (5)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl10.38891 (3)0.69710 (12)0.18830 (6)0.0741 (3)
Cl20.86516 (3)1.12252 (11)0.50704 (6)0.0673 (2)
O20.48266 (8)1.0458 (3)0.48167 (13)0.0652 (6)
O10.76678 (8)0.5045 (3)0.22142 (13)0.0620 (5)
N10.73924 (8)0.6319 (3)0.39935 (13)0.0373 (4)
N20.64367 (8)0.7006 (3)0.45277 (14)0.0434 (5)
N40.60866 (9)1.2130 (3)0.24891 (14)0.0403 (5)
C60.57814 (10)0.6745 (3)0.32064 (17)0.0387 (6)
N30.51184 (8)1.1689 (3)0.30384 (13)0.0368 (4)
C70.63898 (10)0.6637 (3)0.36576 (16)0.0345 (5)
C210.61298 (10)1.1699 (3)0.33495 (17)0.0370 (5)
C110.83204 (12)0.6244 (4)0.48197 (19)0.0507 (7)
H110.87500.60380.48570.061*
C170.79144 (11)1.1336 (4)0.45777 (19)0.0467 (6)
C140.70483 (10)0.6813 (3)0.47280 (16)0.0400 (6)
C200.67494 (10)1.1586 (3)0.37871 (17)0.0376 (6)
C80.69729 (10)0.6195 (3)0.32942 (16)0.0360 (5)
C280.54724 (10)1.2129 (3)0.23030 (16)0.0384 (6)
C180.78521 (11)1.0860 (4)0.37049 (19)0.0489 (6)
H180.81981.04670.33820.059*
C220.55419 (10)1.1401 (3)0.37297 (16)0.0380 (5)
C190.72678 (10)1.0975 (3)0.33157 (17)0.0423 (6)
H190.72211.06380.27280.051*
C20.51455 (11)0.7437 (4)0.1929 (2)0.0505 (6)
H20.51100.78460.13500.061*
C90.71397 (11)0.5482 (3)0.24447 (17)0.0434 (6)
H90.68190.53400.20350.052*
C50.52395 (11)0.6241 (3)0.36600 (18)0.0448 (6)
H50.52680.58460.42420.054*
C240.44781 (11)1.1572 (3)0.30118 (19)0.0462 (6)
H240.42511.12740.35150.055*
C270.51591 (12)1.2473 (4)0.15048 (19)0.0492 (6)
H270.53841.27860.10010.059*
C130.73559 (11)0.7049 (4)0.55341 (19)0.0507 (7)
H130.71330.74010.60330.061*
C100.80304 (10)0.6045 (3)0.40399 (19)0.0446 (6)
H100.82570.57270.35390.054*
C260.45240 (12)1.2345 (4)0.14768 (19)0.0526 (7)
H260.43141.25540.09490.063*
C10.57237 (11)0.7353 (4)0.23404 (18)0.0439 (6)
H10.60800.77090.20320.053*
C160.74146 (11)1.1959 (4)0.5060 (2)0.0497 (6)
H160.74661.22860.56490.060*
C40.46599 (12)0.6322 (4)0.32548 (19)0.0497 (6)
H40.43000.59880.35610.060*
C230.53638 (11)1.0703 (3)0.45701 (17)0.0463 (6)
H230.56831.04100.49630.056*
C150.68309 (11)1.2097 (4)0.46614 (18)0.0468 (6)
H150.64911.25360.49830.056*
C120.79878 (12)0.6758 (4)0.5579 (2)0.0513 (7)
H120.81970.68990.61120.062*
C250.41833 (12)1.1899 (4)0.22393 (19)0.0514 (7)
H250.37491.18270.22120.062*
C30.46229 (12)0.6899 (4)0.23968 (19)0.0485 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0499 (4)0.0888 (6)0.0835 (6)0.0081 (4)−0.0283 (4)−0.0004 (5)
Cl20.0459 (3)0.0834 (5)0.0725 (5)−0.0041 (3)−0.0179 (3)0.0060 (4)
O20.0454 (10)0.0979 (15)0.0524 (12)−0.0022 (10)0.0123 (9)0.0151 (11)
O10.0459 (10)0.0937 (16)0.0462 (12)0.0041 (10)0.0086 (9)−0.0156 (10)
N10.0354 (10)0.0400 (11)0.0365 (12)−0.0013 (8)−0.0023 (9)−0.0030 (8)
N20.0392 (10)0.0512 (13)0.0399 (14)0.0004 (9)0.0005 (10)−0.0062 (10)
N40.0380 (10)0.0492 (12)0.0337 (12)−0.0002 (9)0.0021 (9)−0.0003 (9)
C60.0399 (13)0.0367 (12)0.0393 (15)0.0020 (10)−0.0026 (11)−0.0046 (11)
N30.0343 (10)0.0400 (10)0.0361 (12)0.0006 (8)−0.0024 (9)−0.0024 (8)
C70.0354 (11)0.0351 (12)0.0331 (13)0.0008 (9)−0.0014 (10)−0.0026 (10)
C210.0393 (12)0.0365 (12)0.0354 (14)0.0017 (10)0.0030 (11)−0.0013 (10)
C110.0389 (12)0.0547 (16)0.0585 (19)0.0020 (11)−0.0094 (13)−0.0043 (13)
C170.0409 (13)0.0476 (15)0.0517 (18)−0.0066 (11)−0.0098 (13)0.0087 (12)
C140.0388 (12)0.0448 (14)0.0364 (15)0.0006 (11)0.0010 (11)−0.0068 (10)
C200.0357 (12)0.0385 (13)0.0384 (15)−0.0040 (9)−0.0001 (10)0.0044 (11)
C80.0366 (12)0.0379 (12)0.0337 (13)−0.0032 (9)−0.0010 (10)0.0000 (10)
C280.0377 (12)0.0444 (14)0.0333 (14)−0.0012 (10)0.0025 (10)−0.0032 (10)
C180.0387 (13)0.0547 (17)0.0533 (18)0.0038 (11)0.0035 (12)0.0056 (13)
C220.0352 (12)0.0413 (13)0.0375 (14)0.0011 (9)0.0005 (11)−0.0015 (10)
C190.0411 (13)0.0500 (14)0.0359 (14)0.0018 (10)0.0011 (11)0.0014 (11)
C20.0561 (15)0.0541 (17)0.0411 (16)0.0085 (12)−0.0045 (14)0.0009 (13)
C90.0438 (13)0.0479 (15)0.0385 (14)−0.0032 (11)0.0001 (11)−0.0027 (11)
C50.0418 (13)0.0505 (15)0.0421 (15)0.0007 (10)0.0016 (11)−0.0004 (12)
C240.0359 (12)0.0513 (15)0.0513 (17)−0.0028 (11)0.0038 (12)−0.0016 (12)
C270.0536 (15)0.0571 (16)0.0368 (16)−0.0002 (12)−0.0031 (13)−0.0029 (12)
C130.0513 (15)0.0651 (17)0.0357 (16)0.0014 (13)−0.0052 (13)−0.0103 (13)
C100.0341 (12)0.0499 (15)0.0497 (16)0.0014 (11)0.0010 (11)−0.0045 (12)
C260.0545 (15)0.0571 (16)0.0463 (18)0.0074 (13)−0.0121 (14)−0.0076 (13)
C10.0408 (13)0.0475 (15)0.0435 (17)0.0017 (11)0.0008 (11)0.0011 (11)
C160.0509 (14)0.0592 (16)0.0389 (16)−0.0058 (12)−0.0078 (13)−0.0015 (13)
C40.0378 (13)0.0559 (16)0.0555 (18)−0.0022 (11)−0.0025 (12)−0.0025 (13)
C230.0425 (13)0.0539 (15)0.0424 (15)−0.0009 (11)0.0028 (12)0.0038 (12)
C150.0449 (13)0.0561 (17)0.0395 (17)−0.0011 (11)0.0036 (12)0.0015 (12)
C120.0503 (15)0.0621 (17)0.0414 (16)−0.0041 (13)−0.0133 (13)−0.0032 (13)
C250.0402 (13)0.0579 (17)0.0560 (18)0.0024 (12)−0.0091 (13)−0.0064 (13)
C30.0421 (13)0.0475 (15)0.0560 (18)0.0069 (11)−0.0129 (13)−0.0065 (13)

Geometric parameters (Å, °)

Cl1—C31.750 (3)C28—C271.406 (4)
Cl2—C171.743 (2)C18—C191.382 (3)
O2—C231.219 (3)C18—H180.9300
O1—C91.221 (3)C22—C231.424 (3)
N1—C101.378 (3)C19—H190.9300
N1—C141.382 (3)C2—C31.378 (4)
N1—C81.391 (3)C2—C11.384 (3)
N2—C141.347 (3)C2—H20.9300
N2—C71.351 (3)C9—H90.9300
N4—C281.341 (3)C5—C41.382 (3)
N4—C211.346 (3)C5—H50.9300
C6—C11.391 (4)C24—C251.351 (4)
C6—C51.394 (3)C24—H240.9300
C6—C71.470 (3)C27—C261.359 (3)
N3—C241.369 (3)C27—H270.9300
N3—C281.385 (3)C13—C121.366 (3)
N3—C221.400 (3)C13—H130.9300
C7—C81.398 (3)C10—H100.9300
C21—C221.397 (3)C26—C251.404 (4)
C21—C201.482 (3)C26—H260.9300
C11—C101.343 (4)C1—H10.9300
C11—C121.403 (4)C16—C151.389 (3)
C11—H110.9300C16—H160.9300
C17—C161.370 (4)C4—C31.370 (4)
C17—C181.375 (4)C4—H40.9300
C14—C131.399 (4)C23—H230.9300
C20—C151.388 (4)C15—H150.9300
C20—C191.390 (3)C12—H120.9300
C8—C91.434 (3)C25—H250.9300
C10—N1—C14121.4 (2)C1—C2—H2120.8
C10—N1—C8131.7 (2)O1—C9—C8125.4 (2)
C14—N1—C8106.87 (18)O1—C9—H9117.3
C14—N2—C7105.8 (2)C8—C9—H9117.3
C28—N4—C21105.7 (2)C4—C5—C6120.8 (3)
C1—C6—C5118.4 (2)C4—C5—H5119.6
C1—C6—C7122.3 (2)C6—C5—H5119.6
C5—C6—C7119.2 (2)C25—C24—N3118.6 (2)
C24—N3—C28122.3 (2)C25—C24—H24120.7
C24—N3—C22131.1 (2)N3—C24—H24120.7
C28—N3—C22106.61 (18)C26—C27—C28119.3 (3)
N2—C7—C8111.4 (2)C26—C27—H27120.4
N2—C7—C6120.7 (2)C28—C27—H27120.4
C8—C7—C6127.9 (2)C12—C13—C14119.2 (2)
N4—C21—C22112.0 (2)C12—C13—H13120.4
N4—C21—C20120.6 (2)C14—C13—H13120.4
C22—C21—C20127.4 (2)C11—C10—N1119.0 (2)
C10—C11—C12121.3 (2)C11—C10—H10120.5
C10—C11—H11119.4N1—C10—H10120.5
C12—C11—H11119.4C27—C26—C25120.4 (3)
C16—C17—C18121.5 (2)C27—C26—H26119.8
C16—C17—Cl2119.2 (2)C25—C26—H26119.8
C18—C17—Cl2119.3 (2)C2—C1—C6121.2 (2)
N2—C14—N1111.1 (2)C2—C1—H1119.4
N2—C14—C13129.7 (2)C6—C1—H1119.4
N1—C14—C13119.2 (2)C17—C16—C15119.2 (3)
C15—C20—C19118.5 (2)C17—C16—H16120.4
C15—C20—C21121.7 (2)C15—C16—H16120.4
C19—C20—C21119.8 (2)C3—C4—C5119.2 (3)
N1—C8—C7104.9 (2)C3—C4—H4120.4
N1—C8—C9123.3 (2)C5—C4—H4120.4
C7—C8—C9131.1 (2)O2—C23—C22125.3 (2)
N4—C28—N3111.3 (2)O2—C23—H23117.3
N4—C28—C27130.3 (2)C22—C23—H23117.3
N3—C28—C27118.4 (2)C20—C15—C16120.7 (2)
C17—C18—C19118.9 (2)C20—C15—H15119.7
C17—C18—H18120.5C16—C15—H15119.7
C19—C18—H18120.5C13—C12—C11120.0 (3)
C21—C22—N3104.3 (2)C13—C12—H12120.0
C21—C22—C23131.6 (2)C11—C12—H12120.0
N3—C22—C23123.5 (2)C24—C25—C26121.0 (2)
C18—C19—C20121.1 (2)C24—C25—H25119.5
C18—C19—H19119.4C26—C25—H25119.5
C20—C19—H19119.4C4—C3—C2122.0 (2)
C3—C2—C1118.5 (3)C4—C3—Cl1119.0 (2)
C3—C2—H2120.8C2—C3—Cl1119.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C11—H11···O2i0.932.543.442 (3)163
C12—H12···N4ii0.932.593.518 (4)172

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5204).

References

  • Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Burkholder, C., Dolbier, W. R., Medebielle, M. & Ait-Mohand, S. (2001). Tetrahedron Lett. 42, 3077–3080.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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