Literature DB >> 21588439

Ethyl 5,8-dibromo-2-dibromo-methyl-6,7-dimeth-oxyquinoline-3-carb-oxy-late.

Ting Zhou1, Yu-Hua Long, Ding-Qiao Yang, Han-Mei Zhang, Wen-Ling Wang.   

Abstract

The title compound, C(15)H(13)Br(4)NO(4), was obtained via radical bromination reaction of ethyl 6,7-dimeth-oxy-2-methyl-quinoline-3-carboxyl-ate and N-bromo-succinimide (NBS) in the presence of benzoyl peroxide (BPO) under photocatalytic conditions. The quinoline ring system is approximately planar with a maximum deviation from the mean plane of 0.035 (1) Å. The dihedral angle between the six-membered rings is 2.33 (2)°. The meth-oxy O atoms of the two neighboring meth-oxy groups are in-plane while their methyl C atoms are located on either side of the quinolyl ring plane at distances of -1.207 (1) and 1.223 (1) Å.

Entities:  

Year:  2010        PMID： 21588439      PMCID： PMC3007515          DOI： 10.1107/S1600536810029351

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

The quinoline nucleus is widely present in numerous natural compounds, see: Michael et al. (1997 ▶, 2002 ▶). For the biological activity of quinoline derivatives, see: Heath et al. (2004 ▶); Keyaerts et al. (2004 ▶); Ko et al. (2001 ▶). For our previous work on the preparation of quinoline derivatives, see: Yang et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C15H13Br4NO4 M = 590.90 Triclinic, a = 8.992 (2) Å b = 9.632 (2) Å c = 11.454 (3) Å α = 84.868 (3)° β = 71.948 (3)° γ = 77.552 (3)° V = 920.8 (4) Å3 Z = 2 Mo Kα radiation μ = 8.76 mm−1 T = 298 K 0.25 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.218, T max = 0.302 4750 measured reflections 3257 independent reflections 2373 reflections with I > 2σ(I) R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.105 S = 0.97 3257 reflections 220 parameters H-atom parameters constrained Δρmax = 0.97 e Å−3 Δρmin = −0.74 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks quinoline, I. DOI: 10.1107/S1600536810029351/si2277sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029351/si2277Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H13Br4NO4Z = 2
Mr = 590.90F(000) = 564
Triclinic, P1Dx = 2.131 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.992 (2) ÅCell parameters from 3257 reflections
b = 9.632 (2) Åθ = 1.9–25.2°
c = 11.454 (3) ŵ = 8.76 mm−1
α = 84.868 (3)°T = 298 K
β = 71.948 (3)°Block, colourless
γ = 77.552 (3)°0.25 × 0.20 × 0.18 mm
V = 920.8 (4) Å3
Bruker APEXII CCD area detector diffractometer3257 independent reflections
Radiation source: fine-focus sealed tube2373 reflections with I > 2σ(I)
graphiteRint = 0.035
phi and ω scansθmax = 25.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)h = −10→10
Tmin = 0.218, Tmax = 0.302k = −8→11
4750 measured reflectionsl = −13→13
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.0511P)2] where P = (Fo2 + 2Fc2)/3
3257 reflections(Δ/σ)max = 0.001
220 parametersΔρmax = 0.97 e Å−3
0 restraintsΔρmin = −0.74 e Å−3
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.
xyzUiso*/Ueq
Br10.57694 (8)1.26070 (8)0.23987 (7)0.0629 (2)
Br20.89932 (9)1.37644 (7)0.12167 (7)0.0596 (2)
Br31.17101 (7)1.17543 (6)0.39139 (6)0.04485 (19)
Br41.13760 (9)0.53496 (6)0.26742 (6)0.0561 (2)
C11.2668 (10)0.5760 (8)0.5327 (7)0.075 (2)
H18A1.24220.65360.58700.112*
H18B1.34240.49980.55470.112*
H18C1.17100.54300.53930.112*
C21.5111 (8)0.8569 (7)0.4025 (6)0.0580 (18)
H15A1.53510.77020.35920.087*
H15B1.56880.84490.46180.087*
H15C1.54190.93230.34540.087*
C31.2399 (6)0.7379 (5)0.3697 (5)0.0342 (12)
C41.1433 (6)0.7213 (5)0.3041 (5)0.0336 (12)
C51.2496 (6)0.8762 (5)0.3958 (5)0.0314 (12)
C61.1574 (6)0.9927 (5)0.3568 (5)0.0298 (11)
C71.0550 (6)0.9772 (5)0.2876 (4)0.0283 (11)
C81.0484 (6)0.8386 (5)0.2603 (5)0.0304 (12)
C90.9471 (6)0.8295 (5)0.1901 (5)0.0345 (12)
H190.93630.74050.17230.041*
C100.8643 (6)0.9490 (5)0.1478 (5)0.0333 (12)
C110.8822 (6)1.0830 (5)0.1777 (5)0.0321 (12)
C120.7951 (6)1.2193 (5)0.1337 (5)0.0364 (13)
H140.79171.20350.05130.044*
C130.7654 (7)0.9337 (6)0.0670 (5)0.0397 (13)
C140.6348 (9)0.7820 (7)0.0037 (6)0.072 (2)
H16A0.70740.7516−0.07600.086*
H16B0.56010.8673−0.00790.086*
C150.5464 (10)0.6653 (8)0.0669 (7)0.082 (3)
H17A0.62130.58370.08200.123*
H17B0.49100.63960.01520.123*
H17C0.47090.69880.14350.123*
N10.9716 (5)1.0961 (4)0.2468 (4)0.0330 (10)
O10.7234 (5)0.8094 (4)0.0843 (4)0.0535 (12)
O20.7315 (5)1.0223 (5)−0.0062 (4)0.0556 (12)
O31.3345 (5)0.6235 (4)0.4075 (4)0.0436 (10)
O41.3441 (5)0.8917 (4)0.4638 (3)0.0429 (10)
U11U22U33U12U13U23
Br10.0304 (4)0.0793 (5)0.0675 (5)0.0064 (3)−0.0113 (3)0.0034 (4)
Br20.0622 (5)0.0435 (4)0.0804 (5)−0.0165 (3)−0.0315 (4)0.0111 (3)
Br30.0409 (4)0.0368 (3)0.0633 (4)−0.0074 (3)−0.0231 (3)−0.0080 (3)
Br40.0643 (5)0.0319 (3)0.0826 (5)−0.0068 (3)−0.0370 (4)−0.0071 (3)
C10.069 (6)0.070 (5)0.076 (6)0.002 (4)−0.027 (5)0.025 (4)
C20.038 (4)0.073 (5)0.072 (5)−0.013 (3)−0.023 (4)−0.016 (3)
C30.030 (3)0.031 (3)0.038 (3)0.000 (2)−0.009 (3)−0.003 (2)
C40.027 (3)0.028 (3)0.048 (3)−0.003 (2)−0.013 (3)−0.005 (2)
C50.025 (3)0.033 (3)0.036 (3)−0.002 (2)−0.011 (2)−0.003 (2)
C60.020 (3)0.029 (3)0.040 (3)−0.005 (2)−0.007 (2)−0.006 (2)
C70.018 (3)0.033 (3)0.032 (3)−0.003 (2)−0.006 (2)−0.003 (2)
C80.023 (3)0.032 (3)0.036 (3)−0.005 (2)−0.008 (2)−0.003 (2)
C90.030 (3)0.033 (3)0.042 (3)−0.007 (2)−0.012 (3)−0.001 (2)
C100.022 (3)0.044 (3)0.037 (3)−0.009 (2)−0.010 (2)−0.002 (2)
C110.021 (3)0.032 (3)0.039 (3)0.000 (2)−0.006 (2)−0.002 (2)
C120.030 (3)0.037 (3)0.043 (3)−0.004 (2)−0.015 (3)0.001 (2)
C130.023 (3)0.053 (4)0.043 (3)−0.006 (3)−0.010 (3)−0.005 (3)
C140.079 (6)0.084 (5)0.083 (5)−0.030 (5)−0.057 (5)−0.003 (4)
C150.089 (7)0.104 (6)0.091 (6)−0.060 (5)−0.060 (5)0.021 (5)
N10.028 (3)0.033 (2)0.038 (3)−0.004 (2)−0.013 (2)0.0012 (19)
O10.064 (3)0.051 (2)0.068 (3)−0.021 (2)−0.045 (3)0.004 (2)
O20.060 (3)0.063 (3)0.061 (3)−0.017 (2)−0.042 (3)0.008 (2)
O30.033 (2)0.036 (2)0.060 (3)0.0060 (18)−0.021 (2)0.0009 (18)
O40.037 (3)0.051 (2)0.049 (2)−0.0027 (19)−0.026 (2)−0.0097 (18)
Br1—C121.939 (6)C7—N11.358 (6)
Br2—C121.919 (5)C7—C81.415 (6)
Br3—C61.876 (4)C8—C91.409 (6)
Br4—C41.894 (5)C9—C101.367 (7)
C1—O31.449 (8)C9—H190.9300
C1—H18A0.9600C10—C111.418 (7)
C1—H18B0.9600C10—C131.504 (7)
C1—H18C0.9600C11—N11.322 (6)
C2—O41.426 (7)C11—C121.507 (7)
C2—H15A0.9600C12—H140.9800
C2—H15B0.9600C13—O21.200 (6)
C2—H15C0.9600C13—O11.313 (6)
C3—C41.353 (7)C14—O11.465 (6)
C3—O31.365 (6)C14—C151.517 (11)
C3—C51.417 (7)C14—H16A0.9700
C4—C81.415 (7)C14—H16B0.9700
C5—O41.355 (5)C15—H17A0.9600
C5—C61.373 (7)C15—H17B0.9600
C6—C71.425 (6)C15—H17C0.9600
O3—C1—H18A109.5C8—C9—H19119.4
O3—C1—H18B109.5C9—C10—C11118.0 (4)
H18A—C1—H18B109.5C9—C10—C13119.2 (5)
O3—C1—H18C109.5C11—C10—C13122.8 (5)
H18A—C1—H18C109.5N1—C11—C10122.7 (5)
H18B—C1—H18C109.5N1—C11—C12116.4 (4)
O4—C2—H15A109.5C10—C11—C12120.9 (4)
O4—C2—H15B109.5C11—C12—Br2113.1 (3)
H15A—C2—H15B109.5C11—C12—Br1109.2 (4)
O4—C2—H15C109.5Br2—C12—Br1111.5 (3)
H15A—C2—H15C109.5C11—C12—H14107.6
H15B—C2—H15C109.5Br2—C12—H14107.6
C4—C3—O3121.2 (4)Br1—C12—H14107.6
C4—C3—C5120.0 (5)O2—C13—O1123.9 (5)
O3—C3—C5118.7 (4)O2—C13—C10124.7 (5)
C3—C4—C8122.2 (4)O1—C13—C10111.4 (5)
C3—C4—Br4118.8 (4)O1—C14—C15106.3 (4)
C8—C4—Br4119.0 (3)O1—C14—H16A110.5
O4—C5—C6120.8 (4)C15—C14—H16A110.5
O4—C5—C3119.6 (4)O1—C14—H16B110.5
C6—C5—C3119.6 (4)C15—C14—H16B110.5
C5—C6—C7121.1 (4)H16A—C14—H16B108.7
C5—C6—Br3119.4 (3)C14—C15—H17A109.5
C7—C6—Br3119.5 (4)C14—C15—H17B109.5
N1—C7—C8122.5 (4)H17A—C15—H17B109.5
N1—C7—C6118.7 (4)C14—C15—H17C109.5
C8—C7—C6118.7 (4)H17A—C15—H17C109.5
C9—C8—C4125.3 (4)H17B—C15—H17C109.5
C9—C8—C7116.4 (4)C11—N1—C7119.2 (4)
C4—C8—C7118.3 (4)C13—O1—C14115.0 (4)
C10—C9—C8121.2 (5)C3—O3—C1114.0 (5)
C10—C9—H19119.4C5—O4—C2114.8 (4)
O3—C3—C4—C8−177.7 (5)C8—C9—C10—C11−0.6 (8)
C5—C3—C4—C8−0.5 (8)C8—C9—C10—C13176.4 (5)
O3—C3—C4—Br41.2 (7)C9—C10—C11—N1−1.7 (8)
C5—C3—C4—Br4178.4 (4)C13—C10—C11—N1−178.7 (5)
C4—C3—C5—O4178.6 (5)C9—C10—C11—C12179.8 (5)
O3—C3—C5—O4−4.1 (7)C13—C10—C11—C122.8 (8)
C4—C3—C5—C61.6 (8)N1—C11—C12—Br226.6 (6)
O3—C3—C5—C6178.9 (5)C10—C11—C12—Br2−154.9 (4)
O4—C5—C6—C7−178.5 (5)N1—C11—C12—Br1−98.2 (5)
C3—C5—C6—C7−1.6 (8)C10—C11—C12—Br180.3 (5)
O4—C5—C6—Br33.2 (7)C9—C10—C13—O2−154.5 (6)
C3—C5—C6—Br3−179.9 (4)C11—C10—C13—O222.4 (9)
C5—C6—C7—N1−177.2 (5)C9—C10—C13—O124.0 (7)
Br3—C6—C7—N11.1 (7)C11—C10—C13—O1−159.1 (5)
C5—C6—C7—C80.5 (7)C10—C11—N1—C72.5 (8)
Br3—C6—C7—C8178.8 (4)C12—C11—N1—C7−179.0 (5)
C3—C4—C8—C9179.0 (5)C8—C7—N1—C11−0.8 (8)
Br4—C4—C8—C90.1 (7)C6—C7—N1—C11176.8 (5)
C3—C4—C8—C7−0.6 (8)O2—C13—O1—C142.1 (9)
Br4—C4—C8—C7−179.5 (4)C10—C13—O1—C14−176.4 (5)
N1—C7—C8—C9−1.4 (7)C15—C14—O1—C13−159.2 (6)
C6—C7—C8—C9−179.0 (5)C4—C3—O3—C1−97.1 (6)
N1—C7—C8—C4178.2 (5)C5—C3—O3—C185.7 (6)
C6—C7—C8—C40.5 (7)C6—C5—O4—C2−111.0 (6)
C4—C8—C9—C10−177.5 (5)C3—C5—O4—C272.0 (6)
C7—C8—C9—C102.1 (8)
  6 in total

1.  Synthesis of 4-alkoxy-2-phenylquinoline derivatives as potent antiplatelet agents.

Authors:  T C Ko; M J Hour; J C Lien; C M Teng; K H Lee; S C Kuo; L J Huang
Journal:  Bioorg Med Chem Lett       Date:  2001-02-12       Impact factor: 2.823

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Identification of 4-piperazin-1-yl-quinazoline template based aryl and benzyl thioureas as potent, selective, and orally bioavailable inhibitors of platelet-derived growth factor (PDGF) receptor.

Authors:  Julie A Heath; Mukund M Mehrotra; Shannon Chi; Jin-Chen Yu; Athiwat Hutchaleelaha; Stanley J Hollenbach; Neill A Giese; Robert M Scarborough; Anjali Pandey
Journal:  Bioorg Med Chem Lett       Date:  2004-10-04       Impact factor: 2.823

Review 4.  Quinoline, quinazoline and acridone alkaloids.

Authors:  Joseph P Michael
Journal:  Nat Prod Rep       Date:  2002-12       Impact factor: 13.423

5.  In vitro inhibition of severe acute respiratory syndrome coronavirus by chloroquine.

Authors:  Els Keyaerts; Leen Vijgen; Piet Maes; Johan Neyts; Marc Van Ranst
Journal:  Biochem Biophys Res Commun       Date:  2004-10-08       Impact factor: 3.575

6.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  6 in total
  1 in total

1.  2-(3-Morpholino-prop-yl)-2,3-dihydro-1H-pyrrolo-[3,4-b]quinolin-1-one monohydrate.

Authors:  Yu-Hua Long; Ting Zhou; Ding-Qiao Yang; Wen-Ling Wang; Han-Mei Zhang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-13
  1 in total

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