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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o201.
Published online 2009 December 19. doi:  10.1107/S1600536809054051
PMCID: PMC2980227

2-Chloro-3-hydroxy­methyl-6-methoxy­quinoline

Abstract

All the non-H atoms of the title compound, C11H10ClNO2, are roughly coplanar (r.m.s. deviation = 0.058 Å). In the crystal, adjacent mol­ecules are linked by an O—H(...)N hydrogen bond, generating chains running along the a axis.

Related literature

Substituted quinoline-3-carbaldehydes are inter­mediates for annelation and functional group modification; for a review of the synthesis of quinolines by the Vilsmeier–Haack reaction, see: Meth-Cohn (1993 [triangle]).

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Object name is e-66-0o201-scheme1.jpg

Experimental

Crystal data

  • C11H10ClNO2
  • M r = 223.65
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o201-efi1.jpg
  • a = 6.9738 (3) Å
  • b = 21.4668 (9) Å
  • c = 7.3479 (4) Å
  • β = 108.220 (5)°
  • V = 1044.87 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.34 mm−1
  • T = 293 K
  • 0.28 × 0.21 × 0.20 mm

Data collection

  • Bruker SMART area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.910, T max = 0.935
  • 11517 measured reflections
  • 2348 independent reflections
  • 1487 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.108
  • S = 0.97
  • 2348 reflections
  • 138 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054051/bt5140sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054051/bt5140Isup2.hkl

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

Acknowledgments

We thank the Department of Science and Technology, India, for use of the diffraction facility at IISc under the IRHPA–DST program. FNK thanks the DST for Fast Track Proposal funding. We thank VIT University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

2-Chloro-8-methoxyquinoline-3-carbaldehyde (220 mg, 1 mmol), sodium borohydride (38 mg, 1 mmol) and a catalytic amount of montmorillonite K-10 were placed in a beaker. The contents were irradiated at 500 W for 5 min. The product was dissolved in ethyl acetate and the residue removed by filtration. The filtrate was subjected to column chromatography on silica, and ethyl acetate/petroleum ether was used as the eluant. The solvent was evaporated and the residue recrystallized from chloroform to give colorless crystals.

Refinement

Hydrogen atoms were placed in calculated positions (C–H 0.93–0.97, O–H 0.82 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C,O).

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of C11H10ClNO2 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C11H10ClNO2F(000) = 464
Mr = 223.65Dx = 1.422 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1941 reflections
a = 6.9738 (3) Åθ = 3.1–25.5°
b = 21.4668 (9) ŵ = 0.34 mm1
c = 7.3479 (4) ÅT = 293 K
β = 108.220 (5)°Block, colorless
V = 1044.87 (8) Å30.28 × 0.21 × 0.20 mm
Z = 4

Data collection

Bruker SMART area-detector diffractometer2348 independent reflections
Radiation source: fine-focus sealed tube1487 reflections with I > 2σ(I)
graphiteRint = 0.035
[var phi] and ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→8
Tmin = 0.910, Tmax = 0.935k = −26→27
11517 measured reflectionsl = −9→9

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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.058P)2] where P = (Fo2 + 2Fc2)/3
2348 reflections(Δ/σ)max = 0.001
138 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = −0.25 e Å3

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

xyzUiso*/Ueq
Cl10.33210 (8)0.65210 (2)0.10064 (7)0.0648 (2)
O10.97027 (18)0.59162 (7)0.33602 (19)0.0672 (4)
H11.02000.57900.25540.101*
O20.4314 (2)0.29302 (7)0.3876 (2)0.0766 (5)
N10.2607 (2)0.53770 (7)0.16969 (18)0.0446 (4)
C10.4061 (3)0.57605 (8)0.1763 (2)0.0430 (4)
C20.6156 (2)0.56246 (8)0.2401 (2)0.0408 (4)
C30.6650 (2)0.50291 (8)0.2994 (2)0.0437 (4)
H30.80040.49160.34610.052*
C40.5149 (2)0.45775 (8)0.2917 (2)0.0390 (4)
C50.5600 (3)0.39542 (9)0.3483 (2)0.0494 (5)
H50.69350.38210.39260.059*
C60.4070 (3)0.35449 (9)0.3379 (2)0.0526 (5)
C70.2053 (3)0.37443 (9)0.2741 (2)0.0546 (5)
H70.10270.34630.26980.065*
C80.1583 (3)0.43397 (9)0.2189 (2)0.0507 (5)
H80.02380.44630.17580.061*
C90.3120 (2)0.47761 (8)0.2261 (2)0.0405 (4)
C100.7702 (3)0.61178 (9)0.2442 (3)0.0528 (5)
H10A0.75750.62400.11380.063*
H10B0.74300.64820.31030.063*
C110.6296 (4)0.26820 (11)0.4324 (4)0.0912 (8)
H11A0.67990.27470.32630.137*
H11B0.62640.22440.45730.137*
H11C0.71630.28870.54390.137*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0574 (3)0.0603 (3)0.0736 (4)0.0151 (2)0.0158 (3)0.0111 (3)
O10.0365 (8)0.0931 (11)0.0762 (9)−0.0030 (7)0.0235 (7)−0.0079 (8)
O20.0887 (12)0.0522 (9)0.0807 (10)0.0010 (8)0.0147 (8)0.0016 (7)
N10.0306 (8)0.0591 (9)0.0412 (8)0.0057 (7)0.0069 (6)−0.0035 (7)
C10.0389 (10)0.0539 (10)0.0365 (9)0.0122 (8)0.0123 (8)−0.0006 (8)
C20.0347 (9)0.0573 (11)0.0341 (8)0.0033 (8)0.0161 (7)−0.0036 (8)
C30.0277 (9)0.0628 (11)0.0403 (9)0.0106 (8)0.0103 (7)−0.0021 (8)
C40.0328 (9)0.0524 (10)0.0307 (8)0.0059 (8)0.0083 (7)−0.0051 (7)
C50.0420 (11)0.0593 (12)0.0428 (10)0.0127 (9)0.0076 (8)−0.0032 (9)
C60.0589 (13)0.0534 (12)0.0427 (10)−0.0005 (9)0.0119 (9)−0.0073 (9)
C70.0504 (12)0.0631 (13)0.0476 (10)−0.0115 (10)0.0115 (9)−0.0095 (9)
C80.0334 (10)0.0698 (13)0.0443 (10)−0.0022 (9)0.0056 (8)−0.0093 (9)
C90.0334 (9)0.0559 (11)0.0304 (8)0.0047 (8)0.0070 (7)−0.0069 (8)
C100.0433 (11)0.0653 (12)0.0547 (11)0.0001 (9)0.0223 (9)0.0013 (10)
C110.113 (2)0.0600 (14)0.1016 (18)0.0275 (14)0.0342 (16)0.0121 (13)

Geometric parameters (Å, °)

Cl1—C11.7496 (18)C4—C91.411 (2)
O1—C101.414 (2)C5—C61.366 (2)
O1—H10.8200C5—H50.9300
O2—C61.366 (2)C6—C71.403 (3)
O2—C111.421 (3)C7—C81.350 (3)
N1—C11.295 (2)C7—H70.9300
N1—C91.368 (2)C8—C91.412 (2)
C1—C21.418 (2)C8—H80.9300
C2—C31.360 (2)C10—H10A0.9700
C2—C101.505 (2)C10—H10B0.9700
C3—C41.415 (2)C11—H11A0.9600
C3—H30.9300C11—H11B0.9600
C4—C51.407 (2)C11—H11C0.9600
C10—O1—H1109.5C8—C7—C6120.86 (18)
C6—O2—C11117.08 (18)C8—C7—H7119.6
C1—N1—C9117.42 (14)C6—C7—H7119.6
N1—C1—C2126.53 (16)C7—C8—C9120.44 (17)
N1—C1—Cl1115.57 (13)C7—C8—H8119.8
C2—C1—Cl1117.90 (14)C9—C8—H8119.8
C3—C2—C1115.52 (16)N1—C9—C4121.87 (16)
C3—C2—C10123.17 (16)N1—C9—C8119.38 (15)
C1—C2—C10121.30 (16)C4—C9—C8118.75 (16)
C2—C3—C4121.42 (16)O1—C10—C2112.82 (16)
C2—C3—H3119.3O1—C10—H10A109.0
C4—C3—H3119.3C2—C10—H10A109.0
C5—C4—C9119.71 (16)O1—C10—H10B109.0
C5—C4—C3123.07 (16)C2—C10—H10B109.0
C9—C4—C3117.21 (15)H10A—C10—H10B107.8
C6—C5—C4119.79 (17)O2—C11—H11A109.5
C6—C5—H5120.1O2—C11—H11B109.5
C4—C5—H5120.1H11A—C11—H11B109.5
O2—C6—C5125.23 (18)O2—C11—H11C109.5
O2—C6—C7114.34 (18)H11A—C11—H11C109.5
C5—C6—C7120.43 (18)H11B—C11—H11C109.5
C9—N1—C1—C2−1.4 (2)C4—C5—C6—C7−1.1 (3)
C9—N1—C1—Cl1179.45 (10)O2—C6—C7—C8−179.55 (16)
N1—C1—C2—C30.1 (2)C5—C6—C7—C81.1 (3)
Cl1—C1—C2—C3179.24 (12)C6—C7—C8—C9−0.6 (3)
N1—C1—C2—C10−178.78 (16)C1—N1—C9—C40.9 (2)
Cl1—C1—C2—C100.4 (2)C1—N1—C9—C8−179.17 (15)
C1—C2—C3—C41.7 (2)C5—C4—C9—N1179.93 (14)
C10—C2—C3—C4−179.43 (15)C3—C4—C9—N10.8 (2)
C2—C3—C4—C5178.76 (15)C5—C4—C9—C80.0 (2)
C2—C3—C4—C9−2.1 (2)C3—C4—C9—C8−179.16 (14)
C9—C4—C5—C60.5 (2)C7—C8—C9—N1−179.89 (15)
C3—C4—C5—C6179.60 (16)C7—C8—C9—C40.1 (2)
C11—O2—C6—C5−7.7 (3)C3—C2—C10—O1−6.8 (2)
C11—O2—C6—C7173.00 (17)C1—C2—C10—O1171.94 (14)
C4—C5—C6—O2179.68 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.822.162.913 (2)153

Symmetry codes: (i) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5140).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2004). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Meth-Cohn, O. (1993). Heterocycles, 35, 539–557.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). publCIF In preparation.

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