PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1519.
Published online 2008 July 19. doi:  10.1107/S1600536808021788
PMCID: PMC2962145

5-(Chloro­meth­yl)quinolin-8-yl acetate

Abstract

The title compound, C12H10ClNO2, crystallizes with two independent mol­ecules in the asymmetric unit; these are approximate mirror images of each other. In each mol­ecule, the chloro­methyl and acetate groups lie on the same side of the quinoline ring system, with dihedral angles between the ring plane and the plane of the acetate group of 82.0 (1) and −79.2 (1)°. The C—C—C—Cl torsion angles for the chloro­methyl groups of the two mol­ecules are 80.9 (2) and −83.1 (2)°.

Related literature

For related literature, see: Chen & Shi (1998 [triangle]); Marian (1966 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1519-scheme1.jpg

Experimental

Crystal data

  • C12H10ClNO2
  • M r = 235.66
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1519-efi1.jpg
  • a = 9.2299 (10) Å
  • b = 11.0042 (13) Å
  • c = 11.2429 (13) Å
  • α = 105.073 (4)°
  • β = 94.105 (1)°
  • γ = 90.815 (2)°
  • V = 1099.2 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.33 mm−1
  • T = 295 K
  • 0.22 × 0.18 × 0.16 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.931, T max = 0.949
  • 5721 measured reflections
  • 3843 independent reflections
  • 3247 reflections with I > 2σ(I)
  • R int = 0.015

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.096
  • S = 1.04
  • 3843 reflections
  • 289 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021788/bi2295sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021788/bi2295Isup2.hkl

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

Acknowledgments

This project was supported by the Foundation of Dongchang College, Liaocheng University (grant No. LG0801).

supplementary crystallographic information

Comment

8-Hydroxyquinoline and its derivatives are amongst the most extensively investigated ligands in coordination chemistry (Chen & Shi, 1998). In the course of our studies on 8-hydroxyquinoline derivatives, we have synthesised the title compound, which is a key intermediate in the synthesis of 8-hydroxyquinoline derivatives.

Experimental

5-(Chloromethyl)quinolin-8-ol hydrochloride (0.0217 mol) (Marian, 1966) and acetic anhydride (25 ml) were added to a 100 ml flask, and refluxed for 6 h. After cooling to room temperature, the mixture was poured into cool water (500 ml). The precipitate was washed with a large amount of water, collected by filtration, and dried to produce the title compound as a grey solid. Colourless single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of an ethanol solution over a period of 2 d.

Refinement

All H atoms were placed in geometrically idealized positions with C(sp2)—H = 0.93, C(methyl)—H = 0.96, and C(methylene)—H = 0.97 Å and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C) (or 1.5Ueq for methyl H).

Figures

Fig. 1.
Two independent molecules in the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted.

Crystal data

C12H10ClNO2Z = 4
Mr = 235.66F000 = 488
Triclinic, P1Dx = 1.424 Mg m3
Hall symbol: -P 1Melting point: 400 K
a = 9.2299 (10) ÅMo Kα radiation λ = 0.71073 Å
b = 11.0042 (13) ÅCell parameters from 3502 reflections
c = 11.2429 (13) Åθ = 2.2–28.2º
α = 105.073 (4)ºµ = 0.33 mm1
β = 94.105 (1)ºT = 295 K
γ = 90.815 (2)ºBlock, colorless
V = 1099.2 (2) Å30.22 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer3843 independent reflections
Radiation source: fine-focus sealed tube3247 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.015
T = 295 Kθmax = 25.1º
[var phi] and ω scansθmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.931, Tmax = 0.949k = −12→13
5721 measured reflectionsl = −12→13

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.096  w = 1/[σ2(Fo2) + (0.0471P)2 + 0.3054P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3843 reflectionsΔρmax = 0.19 e Å3
289 parametersΔρmin = −0.20 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
Cl10.45143 (5)0.67427 (5)0.57622 (4)0.05362 (15)
Cl2−0.04871 (6)0.86602 (4)0.57393 (5)0.05615 (16)
O10.52846 (13)1.00138 (12)0.17138 (11)0.0470 (3)
O20.74973 (16)1.02523 (15)0.27180 (14)0.0658 (4)
O30.03984 (14)0.32842 (11)0.17193 (12)0.0491 (3)
O40.25535 (16)0.36297 (15)0.28101 (15)0.0665 (4)
N10.60339 (17)0.75273 (15)0.11659 (13)0.0479 (4)
N20.11712 (16)0.54988 (15)0.11822 (13)0.0459 (4)
C10.6356 (2)0.6329 (2)0.09146 (18)0.0565 (5)
H10.69420.60230.02700.068*
C20.5871 (2)0.54890 (18)0.15594 (19)0.0566 (5)
H20.61320.46520.13380.068*
C30.5019 (2)0.59019 (17)0.25069 (17)0.0478 (4)
H30.46890.53510.29380.057*
C40.46384 (17)0.71804 (15)0.28332 (15)0.0376 (4)
C50.37582 (18)0.77105 (17)0.38191 (15)0.0400 (4)
C60.3457 (2)0.89608 (18)0.40698 (17)0.0472 (4)
H60.28830.93050.47130.057*
C70.3996 (2)0.97351 (17)0.33765 (17)0.0471 (4)
H70.37821.05840.35620.057*
C80.48297 (18)0.92409 (16)0.24364 (15)0.0393 (4)
C90.51836 (17)0.79539 (16)0.21255 (15)0.0374 (4)
C100.3155 (2)0.6929 (2)0.45894 (18)0.0502 (5)
H10A0.28360.61080.40650.060*
H10B0.23190.73320.49790.060*
C110.6674 (2)1.04787 (17)0.19412 (17)0.0462 (4)
C120.6965 (3)1.1301 (2)0.1117 (2)0.0681 (6)
H12A0.63991.20410.13320.102*
H12B0.67041.08510.02740.102*
H12C0.79791.15420.12130.102*
C130.1446 (2)0.6560 (2)0.09004 (18)0.0542 (5)
H130.20510.65360.02680.065*
C140.0896 (2)0.7722 (2)0.14814 (19)0.0557 (5)
H140.11190.84370.12260.067*
C150.0033 (2)0.77951 (17)0.24219 (17)0.0485 (4)
H15−0.03320.85630.28260.058*
C16−0.03079 (17)0.66915 (16)0.27844 (15)0.0382 (4)
C17−0.11980 (18)0.66651 (17)0.37671 (16)0.0418 (4)
C18−0.1492 (2)0.55457 (19)0.40301 (17)0.0502 (5)
H18−0.20710.55330.46710.060*
C19−0.0938 (2)0.44153 (18)0.33514 (17)0.0490 (4)
H19−0.11590.36610.35350.059*
C20−0.00775 (18)0.44301 (16)0.24263 (16)0.0411 (4)
C210.02808 (17)0.55580 (16)0.21112 (14)0.0373 (4)
C22−0.1815 (2)0.78404 (19)0.45259 (18)0.0527 (5)
H22A−0.26760.76260.48870.063*
H22B−0.20980.83850.40010.063*
C230.1777 (2)0.29749 (18)0.19924 (18)0.0472 (4)
C240.2111 (3)0.1743 (2)0.1156 (2)0.0684 (6)
H24A0.21250.18230.03260.103*
H24B0.13800.11230.11830.103*
H24C0.30440.14860.14170.103*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0594 (3)0.0552 (3)0.0514 (3)−0.0014 (2)−0.0012 (2)0.0249 (2)
Cl20.0605 (3)0.0447 (3)0.0550 (3)0.0013 (2)0.0009 (2)−0.0007 (2)
O10.0496 (7)0.0482 (7)0.0475 (7)−0.0055 (6)−0.0013 (6)0.0223 (6)
O20.0525 (8)0.0773 (10)0.0691 (9)−0.0129 (7)−0.0105 (7)0.0268 (8)
O30.0510 (7)0.0381 (7)0.0513 (7)0.0055 (5)−0.0045 (6)0.0015 (5)
O40.0501 (8)0.0702 (10)0.0749 (10)0.0054 (7)−0.0100 (7)0.0154 (8)
N10.0495 (9)0.0516 (9)0.0409 (8)0.0002 (7)0.0078 (7)0.0081 (7)
N20.0447 (8)0.0536 (9)0.0374 (8)0.0020 (7)0.0028 (6)0.0082 (7)
C10.0581 (12)0.0583 (13)0.0464 (11)0.0065 (10)0.0095 (9)0.0000 (9)
C20.0626 (13)0.0410 (10)0.0609 (12)0.0075 (9)0.0013 (10)0.0043 (9)
C30.0507 (11)0.0403 (10)0.0521 (11)−0.0017 (8)−0.0036 (9)0.0140 (8)
C40.0341 (8)0.0393 (9)0.0383 (8)−0.0027 (7)−0.0046 (7)0.0105 (7)
C50.0329 (9)0.0483 (10)0.0406 (9)−0.0023 (7)−0.0018 (7)0.0161 (8)
C60.0464 (10)0.0529 (11)0.0434 (10)0.0076 (8)0.0101 (8)0.0124 (8)
C70.0525 (11)0.0387 (9)0.0500 (10)0.0065 (8)0.0045 (8)0.0110 (8)
C80.0389 (9)0.0414 (9)0.0390 (9)−0.0044 (7)−0.0031 (7)0.0150 (7)
C90.0345 (9)0.0417 (9)0.0344 (8)−0.0029 (7)−0.0029 (7)0.0090 (7)
C100.0404 (10)0.0624 (12)0.0529 (11)−0.0043 (8)0.0020 (8)0.0247 (9)
C110.0500 (11)0.0407 (10)0.0449 (10)−0.0059 (8)0.0058 (9)0.0054 (8)
C120.0832 (16)0.0607 (13)0.0636 (13)−0.0206 (11)0.0130 (12)0.0212 (11)
C130.0519 (11)0.0681 (14)0.0444 (10)−0.0022 (10)0.0078 (9)0.0171 (9)
C140.0616 (12)0.0541 (12)0.0553 (12)−0.0078 (9)0.0003 (10)0.0231 (10)
C150.0516 (11)0.0388 (10)0.0530 (11)0.0007 (8)−0.0022 (9)0.0103 (8)
C160.0338 (8)0.0393 (9)0.0379 (9)−0.0004 (7)−0.0052 (7)0.0060 (7)
C170.0352 (9)0.0435 (10)0.0423 (9)0.0017 (7)−0.0002 (7)0.0044 (7)
C180.0477 (11)0.0554 (11)0.0463 (10)−0.0038 (8)0.0102 (8)0.0095 (9)
C190.0541 (11)0.0433 (10)0.0509 (10)−0.0041 (8)0.0037 (9)0.0149 (8)
C200.0403 (9)0.0363 (9)0.0420 (9)0.0025 (7)−0.0052 (7)0.0041 (7)
C210.0315 (8)0.0426 (9)0.0347 (8)0.0008 (7)−0.0042 (7)0.0062 (7)
C220.0436 (10)0.0556 (12)0.0526 (11)0.0065 (8)0.0040 (8)0.0022 (9)
C230.0489 (11)0.0473 (10)0.0504 (11)0.0072 (8)0.0062 (9)0.0207 (9)
C240.0816 (16)0.0563 (13)0.0728 (14)0.0253 (11)0.0222 (12)0.0209 (11)

Geometric parameters (Å, °)

Cl1—C101.8072 (19)C10—H10A0.970
Cl2—C221.807 (2)C10—H10B0.970
O1—C111.356 (2)C11—C121.488 (3)
O1—C81.399 (2)C12—H12A0.960
O2—C111.194 (2)C12—H12B0.960
O3—C231.357 (2)C12—H12C0.960
O3—C201.400 (2)C13—C141.397 (3)
O4—C231.193 (2)C13—H130.930
N1—C11.318 (3)C14—C151.355 (3)
N1—C91.367 (2)C14—H140.930
N2—C131.313 (3)C15—C161.416 (3)
N2—C211.364 (2)C15—H150.930
C1—C21.402 (3)C16—C211.418 (2)
C1—H10.930C16—C171.429 (2)
C2—C31.356 (3)C17—C181.367 (3)
C2—H20.930C17—C221.497 (2)
C3—C41.415 (2)C18—C191.404 (3)
C3—H30.930C18—H180.930
C4—C91.417 (2)C19—C201.356 (3)
C4—C51.427 (2)C19—H190.930
C5—C61.367 (3)C20—C211.417 (2)
C5—C101.497 (2)C22—H22A0.970
C6—C71.404 (3)C22—H22B0.970
C6—H60.930C23—C241.486 (3)
C7—C81.354 (2)C24—H24A0.960
C7—H70.930C24—H24B0.960
C8—C91.417 (2)C24—H24C0.960
C11—O1—C8117.15 (14)H12A—C12—H12C109.5
C23—O3—C20117.00 (14)H12B—C12—H12C109.5
C1—N1—C9116.68 (16)N2—C13—C14124.74 (18)
C13—N2—C21116.52 (16)N2—C13—H13117.6
N1—C1—C2123.99 (18)C14—C13—H13117.6
N1—C1—H1118.0C15—C14—C13119.15 (19)
C2—C1—H1118.0C15—C14—H14120.4
C3—C2—C1119.73 (18)C13—C14—H14120.4
C3—C2—H2120.1C14—C15—C16119.46 (18)
C1—C2—H2120.1C14—C15—H15120.3
C2—C3—C4119.31 (18)C16—C15—H15120.3
C2—C3—H3120.3C15—C16—C21116.61 (16)
C4—C3—H3120.3C15—C16—C17123.98 (16)
C9—C4—C3116.66 (16)C21—C16—C17119.42 (16)
C9—C4—C5119.63 (15)C18—C17—C16119.63 (16)
C3—C4—C5123.71 (16)C18—C17—C22118.87 (17)
C6—C5—C4119.42 (16)C16—C17—C22121.50 (17)
C6—C5—C10119.06 (16)C17—C18—C19121.30 (17)
C4—C5—C10121.51 (16)C17—C18—H18119.4
C5—C6—C7121.35 (16)C19—C18—H18119.4
C5—C6—H6119.3C20—C19—C18119.64 (18)
C7—C6—H6119.3C20—C19—H19120.2
C8—C7—C6119.72 (17)C18—C19—H19120.2
C8—C7—H7120.1C19—C20—O3118.62 (16)
C6—C7—H7120.1C19—C20—C21122.02 (16)
C7—C8—O1118.65 (16)O3—C20—C21119.26 (15)
C7—C8—C9121.91 (16)N2—C21—C20118.54 (15)
O1—C8—C9119.34 (15)N2—C21—C16123.49 (16)
N1—C9—C4123.63 (16)C20—C21—C16117.98 (15)
N1—C9—C8118.41 (15)C17—C22—Cl2110.29 (13)
C4—C9—C8117.96 (15)C17—C22—H22A109.6
C5—C10—Cl1110.54 (12)Cl2—C22—H22A109.6
C5—C10—H10A109.5C17—C22—H22B109.6
Cl1—C10—H10A109.5Cl2—C22—H22B109.6
C5—C10—H10B109.5H22A—C22—H22B108.1
Cl1—C10—H10B109.5O4—C23—O3122.23 (17)
H10A—C10—H10B108.1O4—C23—C24127.61 (19)
O2—C11—O1122.74 (17)O3—C23—C24110.15 (18)
O2—C11—C12127.10 (19)C23—C24—H24A109.5
O1—C11—C12110.15 (17)C23—C24—H24B109.5
C11—C12—H12A109.5H24A—C24—H24B109.5
C11—C12—H12B109.5C23—C24—H24C109.5
H12A—C12—H12B109.5H24A—C24—H24C109.5
C11—C12—H12C109.5H24B—C24—H24C109.5
C9—N1—C1—C20.6 (3)C21—N2—C13—C140.0 (3)
N1—C1—C2—C3−0.2 (3)N2—C13—C14—C151.2 (3)
C1—C2—C3—C4−0.3 (3)C13—C14—C15—C16−0.8 (3)
C2—C3—C4—C90.2 (2)C14—C15—C16—C21−0.7 (2)
C2—C3—C4—C5−179.53 (17)C14—C15—C16—C17179.58 (17)
C9—C4—C5—C6−0.2 (2)C15—C16—C17—C18178.55 (17)
C3—C4—C5—C6179.55 (16)C21—C16—C17—C18−1.2 (2)
C9—C4—C5—C10179.84 (15)C15—C16—C17—C22−1.8 (3)
C3—C4—C5—C10−0.4 (2)C21—C16—C17—C22178.48 (15)
C4—C5—C6—C70.0 (3)C16—C17—C18—C19−0.1 (3)
C10—C5—C6—C7179.96 (17)C22—C17—C18—C19−179.78 (17)
C5—C6—C7—C80.2 (3)C17—C18—C19—C200.9 (3)
C6—C7—C8—O1176.36 (15)C18—C19—C20—O3−176.61 (16)
C6—C7—C8—C9−0.1 (3)C18—C19—C20—C21−0.3 (3)
C11—O1—C8—C7102.11 (19)C23—O3—C20—C19−100.93 (19)
C11—O1—C8—C9−81.32 (19)C23—O3—C20—C2182.69 (19)
C1—N1—C9—C4−0.6 (3)C13—N2—C21—C20178.39 (16)
C1—N1—C9—C8179.11 (16)C13—N2—C21—C16−1.7 (2)
C3—C4—C9—N10.2 (2)C19—C20—C21—N2178.97 (16)
C5—C4—C9—N1180.00 (15)O3—C20—C21—N2−4.8 (2)
C3—C4—C9—C8−179.53 (15)C19—C20—C21—C16−0.9 (2)
C5—C4—C9—C80.3 (2)O3—C20—C21—C16175.30 (14)
C7—C8—C9—N1−179.84 (16)C15—C16—C21—N22.0 (2)
O1—C8—C9—N13.7 (2)C17—C16—C21—N2−178.21 (15)
C7—C8—C9—C4−0.1 (2)C15—C16—C21—C20−178.08 (15)
O1—C8—C9—C4−176.54 (14)C17—C16—C21—C201.7 (2)
C6—C5—C10—Cl1−99.09 (17)C18—C17—C22—Cl296.61 (18)
C4—C5—C10—Cl180.86 (18)C16—C17—C22—Cl2−83.08 (19)
C8—O1—C11—O20.1 (3)C20—O3—C23—O41.3 (3)
C8—O1—C11—C12−178.64 (16)C20—O3—C23—C24−179.61 (16)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2295).

References

  • Chen, C. H. & Shi, J. M. (1998). Coord. Chem. Rev.171, 161–174.
  • Marian, K. (1966). J. Heterocycl. Chem.3, 275–277.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • 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