organic compounds
2-Chloro-3-hydroxymethyl-6-methoxyquinoline
aChemistry Division, School of Science and Humanities, VIT University, Vellore 632 014, Tamil Nadu, India, bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
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 ).
modification; for a review of the synthesis of quinolines by the Vilsmeier–Haack reaction, see: Meth-Cohn (1993Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2004); cell SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536809054051/bt5140sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809054051/bt5140Isup2.hkl
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
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.Hydrogen atoms were placed in calculated positions (C–H 0.93–0.97, O–H 0.82 Å) and were included in the
in the riding model approximation, with U(H) set to 1.2–1.5U(C,O).Data collection: SMART (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C11H10ClNO2 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
C11H10ClNO2 | F(000) = 464 |
Mr = 223.65 | Dx = 1.422 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1941 reflections |
a = 6.9738 (3) Å | θ = 3.1–25.5° |
b = 21.4668 (9) Å | µ = 0.34 mm−1 |
c = 7.3479 (4) Å | T = 293 K |
β = 108.220 (5)° | Block, colorless |
V = 1044.87 (8) Å3 | 0.28 × 0.21 × 0.20 mm |
Z = 4 |
Bruker SMART area-detector diffractometer | 2348 independent reflections |
Radiation source: fine-focus sealed tube | 1487 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ϕ and ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→8 |
Tmin = 0.910, Tmax = 0.935 | k = −26→27 |
11517 measured reflections | l = −9→9 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.058P)2] where P = (Fo2 + 2Fc2)/3 |
2348 reflections | (Δ/σ)max = 0.001 |
138 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C11H10ClNO2 | V = 1044.87 (8) Å3 |
Mr = 223.65 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.9738 (3) Å | µ = 0.34 mm−1 |
b = 21.4668 (9) Å | T = 293 K |
c = 7.3479 (4) Å | 0.28 × 0.21 × 0.20 mm |
β = 108.220 (5)° |
Bruker SMART area-detector diffractometer | 2348 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1487 reflections with I > 2σ(I) |
Tmin = 0.910, Tmax = 0.935 | Rint = 0.035 |
11517 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.21 e Å−3 |
2348 reflections | Δρmin = −0.25 e Å−3 |
138 parameters |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.33210 (8) | 0.65210 (2) | 0.10064 (7) | 0.0648 (2) | |
O1 | 0.97027 (18) | 0.59162 (7) | 0.33602 (19) | 0.0672 (4) | |
H1 | 1.0200 | 0.5790 | 0.2554 | 0.101* | |
O2 | 0.4314 (2) | 0.29302 (7) | 0.3876 (2) | 0.0766 (5) | |
N1 | 0.2607 (2) | 0.53770 (7) | 0.16969 (18) | 0.0446 (4) | |
C1 | 0.4061 (3) | 0.57605 (8) | 0.1763 (2) | 0.0430 (4) | |
C2 | 0.6156 (2) | 0.56246 (8) | 0.2401 (2) | 0.0408 (4) | |
C3 | 0.6650 (2) | 0.50291 (8) | 0.2994 (2) | 0.0437 (4) | |
H3 | 0.8004 | 0.4916 | 0.3461 | 0.052* | |
C4 | 0.5149 (2) | 0.45775 (8) | 0.2917 (2) | 0.0390 (4) | |
C5 | 0.5600 (3) | 0.39542 (9) | 0.3483 (2) | 0.0494 (5) | |
H5 | 0.6935 | 0.3821 | 0.3926 | 0.059* | |
C6 | 0.4070 (3) | 0.35449 (9) | 0.3379 (2) | 0.0526 (5) | |
C7 | 0.2053 (3) | 0.37443 (9) | 0.2741 (2) | 0.0546 (5) | |
H7 | 0.1027 | 0.3463 | 0.2698 | 0.065* | |
C8 | 0.1583 (3) | 0.43397 (9) | 0.2189 (2) | 0.0507 (5) | |
H8 | 0.0238 | 0.4463 | 0.1758 | 0.061* | |
C9 | 0.3120 (2) | 0.47761 (8) | 0.2261 (2) | 0.0405 (4) | |
C10 | 0.7702 (3) | 0.61178 (9) | 0.2442 (3) | 0.0528 (5) | |
H10A | 0.7575 | 0.6240 | 0.1138 | 0.063* | |
H10B | 0.7430 | 0.6482 | 0.3103 | 0.063* | |
C11 | 0.6296 (4) | 0.26820 (11) | 0.4324 (4) | 0.0912 (8) | |
H11A | 0.6799 | 0.2747 | 0.3263 | 0.137* | |
H11B | 0.6264 | 0.2244 | 0.4573 | 0.137* | |
H11C | 0.7163 | 0.2887 | 0.5439 | 0.137* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0574 (3) | 0.0603 (3) | 0.0736 (4) | 0.0151 (2) | 0.0158 (3) | 0.0111 (3) |
O1 | 0.0365 (8) | 0.0931 (11) | 0.0762 (9) | −0.0030 (7) | 0.0235 (7) | −0.0079 (8) |
O2 | 0.0887 (12) | 0.0522 (9) | 0.0807 (10) | 0.0010 (8) | 0.0147 (8) | 0.0016 (7) |
N1 | 0.0306 (8) | 0.0591 (9) | 0.0412 (8) | 0.0057 (7) | 0.0069 (6) | −0.0035 (7) |
C1 | 0.0389 (10) | 0.0539 (10) | 0.0365 (9) | 0.0122 (8) | 0.0123 (8) | −0.0006 (8) |
C2 | 0.0347 (9) | 0.0573 (11) | 0.0341 (8) | 0.0033 (8) | 0.0161 (7) | −0.0036 (8) |
C3 | 0.0277 (9) | 0.0628 (11) | 0.0403 (9) | 0.0106 (8) | 0.0103 (7) | −0.0021 (8) |
C4 | 0.0328 (9) | 0.0524 (10) | 0.0307 (8) | 0.0059 (8) | 0.0083 (7) | −0.0051 (7) |
C5 | 0.0420 (11) | 0.0593 (12) | 0.0428 (10) | 0.0127 (9) | 0.0076 (8) | −0.0032 (9) |
C6 | 0.0589 (13) | 0.0534 (12) | 0.0427 (10) | −0.0005 (9) | 0.0119 (9) | −0.0073 (9) |
C7 | 0.0504 (12) | 0.0631 (13) | 0.0476 (10) | −0.0115 (10) | 0.0115 (9) | −0.0095 (9) |
C8 | 0.0334 (10) | 0.0698 (13) | 0.0443 (10) | −0.0022 (9) | 0.0056 (8) | −0.0093 (9) |
C9 | 0.0334 (9) | 0.0559 (11) | 0.0304 (8) | 0.0047 (8) | 0.0070 (7) | −0.0069 (8) |
C10 | 0.0433 (11) | 0.0653 (12) | 0.0547 (11) | 0.0001 (9) | 0.0223 (9) | 0.0013 (10) |
C11 | 0.113 (2) | 0.0600 (14) | 0.1016 (18) | 0.0275 (14) | 0.0342 (16) | 0.0121 (13) |
Cl1—C1 | 1.7496 (18) | C4—C9 | 1.411 (2) |
O1—C10 | 1.414 (2) | C5—C6 | 1.366 (2) |
O1—H1 | 0.8200 | C5—H5 | 0.9300 |
O2—C6 | 1.366 (2) | C6—C7 | 1.403 (3) |
O2—C11 | 1.421 (3) | C7—C8 | 1.350 (3) |
N1—C1 | 1.295 (2) | C7—H7 | 0.9300 |
N1—C9 | 1.368 (2) | C8—C9 | 1.412 (2) |
C1—C2 | 1.418 (2) | C8—H8 | 0.9300 |
C2—C3 | 1.360 (2) | C10—H10A | 0.9700 |
C2—C10 | 1.505 (2) | C10—H10B | 0.9700 |
C3—C4 | 1.415 (2) | C11—H11A | 0.9600 |
C3—H3 | 0.9300 | C11—H11B | 0.9600 |
C4—C5 | 1.407 (2) | C11—H11C | 0.9600 |
C10—O1—H1 | 109.5 | C8—C7—C6 | 120.86 (18) |
C6—O2—C11 | 117.08 (18) | C8—C7—H7 | 119.6 |
C1—N1—C9 | 117.42 (14) | C6—C7—H7 | 119.6 |
N1—C1—C2 | 126.53 (16) | C7—C8—C9 | 120.44 (17) |
N1—C1—Cl1 | 115.57 (13) | C7—C8—H8 | 119.8 |
C2—C1—Cl1 | 117.90 (14) | C9—C8—H8 | 119.8 |
C3—C2—C1 | 115.52 (16) | N1—C9—C4 | 121.87 (16) |
C3—C2—C10 | 123.17 (16) | N1—C9—C8 | 119.38 (15) |
C1—C2—C10 | 121.30 (16) | C4—C9—C8 | 118.75 (16) |
C2—C3—C4 | 121.42 (16) | O1—C10—C2 | 112.82 (16) |
C2—C3—H3 | 119.3 | O1—C10—H10A | 109.0 |
C4—C3—H3 | 119.3 | C2—C10—H10A | 109.0 |
C5—C4—C9 | 119.71 (16) | O1—C10—H10B | 109.0 |
C5—C4—C3 | 123.07 (16) | C2—C10—H10B | 109.0 |
C9—C4—C3 | 117.21 (15) | H10A—C10—H10B | 107.8 |
C6—C5—C4 | 119.79 (17) | O2—C11—H11A | 109.5 |
C6—C5—H5 | 120.1 | O2—C11—H11B | 109.5 |
C4—C5—H5 | 120.1 | H11A—C11—H11B | 109.5 |
O2—C6—C5 | 125.23 (18) | O2—C11—H11C | 109.5 |
O2—C6—C7 | 114.34 (18) | H11A—C11—H11C | 109.5 |
C5—C6—C7 | 120.43 (18) | H11B—C11—H11C | 109.5 |
C9—N1—C1—C2 | −1.4 (2) | C4—C5—C6—C7 | −1.1 (3) |
C9—N1—C1—Cl1 | 179.45 (10) | O2—C6—C7—C8 | −179.55 (16) |
N1—C1—C2—C3 | 0.1 (2) | C5—C6—C7—C8 | 1.1 (3) |
Cl1—C1—C2—C3 | 179.24 (12) | C6—C7—C8—C9 | −0.6 (3) |
N1—C1—C2—C10 | −178.78 (16) | C1—N1—C9—C4 | 0.9 (2) |
Cl1—C1—C2—C10 | 0.4 (2) | C1—N1—C9—C8 | −179.17 (15) |
C1—C2—C3—C4 | 1.7 (2) | C5—C4—C9—N1 | 179.93 (14) |
C10—C2—C3—C4 | −179.43 (15) | C3—C4—C9—N1 | 0.8 (2) |
C2—C3—C4—C5 | 178.76 (15) | C5—C4—C9—C8 | 0.0 (2) |
C2—C3—C4—C9 | −2.1 (2) | C3—C4—C9—C8 | −179.16 (14) |
C9—C4—C5—C6 | 0.5 (2) | C7—C8—C9—N1 | −179.89 (15) |
C3—C4—C5—C6 | 179.60 (16) | C7—C8—C9—C4 | 0.1 (2) |
C11—O2—C6—C5 | −7.7 (3) | C3—C2—C10—O1 | −6.8 (2) |
C11—O2—C6—C7 | 173.00 (17) | C1—C2—C10—O1 | 171.94 (14) |
C4—C5—C6—O2 | 179.68 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.82 | 2.16 | 2.913 (2) | 153 |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C11H10ClNO2 |
Mr | 223.65 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 6.9738 (3), 21.4668 (9), 7.3479 (4) |
β (°) | 108.220 (5) |
V (Å3) | 1044.87 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.34 |
Crystal size (mm) | 0.28 × 0.21 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.910, 0.935 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11517, 2348, 1487 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.108, 0.97 |
No. of reflections | 2348 |
No. of parameters | 138 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.25 |
Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.82 | 2.16 | 2.913 (2) | 153 |
Symmetry code: (i) x+1, y, z. |
Acknowledgements
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.
References
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Meth-Cohn, O. (1993). Heterocycles, 35, 539–557. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar
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