organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Ethyl 1-[(4-acetyl-2-meth­oxy­phen­­oxy)meth­yl]cyclo­propane-1-carboxyl­ate

aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China, bDepartment of Chemical Engineering, Chien-shlung Institute of Technology, Taicang 215411, People's Republic of China, and cDepartment of Applied Chemistry, Nanjing College of Chemical Technology, No. 625 Geguan Road, Dachang, Nanjing 210048, People's Republic of China
*Correspondence e-mail: mhf2356@yahoo.com.cn

(Received 9 December 2008; accepted 8 January 2009; online 14 January 2009)

In the title compound, C16H20O5, the dihedral angle between the planar rings, viz. benzene and cyclo­propane, is 52.1 (2)°. Mol­ecules are connected in the crystal via weak inter­molecular C—H⋯O hydrogen bonds, forming chains in the [001] direction.

Related literature

For details of the synthesis, see: Chen (2008[Chen, G. P. (2008). Advenchen Laboratories, LLC, USA. WO Patent No. 2008112407.]).

[Scheme 1]

Experimental

Crystal data
  • C16H20O5

  • Mr = 292.32

  • Monoclinic, P 21 /c

  • a = 12.663 (3) Å

  • b = 8.5020 (17) Å

  • c = 14.676 (3) Å

  • β = 107.25 (3)°

  • V = 1509.0 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 298 (2) K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.981, Tmax = 0.991

  • 2874 measured reflections

  • 2732 independent reflections

  • 1473 reflections with I > 2σ(I)

  • Rint = 0.039

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 0.168

  • S = 0.93

  • 2732 reflections

  • 193 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C7—H7A⋯O1i 0.93 2.56 3.329 (4) 140
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CAD-4 Software (Enraf–Nonius, 1985[Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound, (I), is one of the most important intermediates in the synthesis of 7-[(1-aminocyclopropyl)methoxy]-N-(1H-indol-5-yl)-6-methoxyquinolin-4-amine, which has advantageous pharmacological properties and inhibits the activity of protein tyrosine kinases (Chen, 2008). We report here the crystal structure of (I).

All bond lengths and angles are within expected ranges. Both benzene and cyclopropane rings are planar, and make a dihedral angle of 52.1 (2)° (rings C3···C8 and C11···C13). Molecules are linked together via intermolecular C—H···O hydrogen bonds, which may be effective to the stabilization of the crystal structure.

Related literature top

For related literature on the synthesis of the title molecule, see: Chen (2008).

Experimental top

The title compound was synthesized using a method similar to that reported recently (Chen, 2008). The crystals were obtained by evaporating the acetone slowly at room temperature for about 14 d.

Refinement top

H atoms were positioned geometrically, with C—H = 0.93 (aromatic), 0.96 (methyl) or 0.97 Å (methylene), and constrained to ride on their parent atoms, with Uiso(H) = xUeq(carrier C), where x = 1.5 for methyl groups and x = 1.2 otherwise. Methyl groups were allowed to rotate about their C—C bonds.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A drawing of the molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. Intramolecular C—H···O hydrogen bond is shown as a dashed line.
[Figure 2] Fig. 2. A packing diagram for (I). C—H···O hydrogen bonds are shown as dashed lines.
Ethyl 1-[(4-acetyl-2-methoxyphenoxy)methyl]cyclopropane-1-carboxylate top
Crystal data top
C16H20O5F(000) = 624
Mr = 292.32Dx = 1.287 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 12.663 (3) Åθ = 9–13°
b = 8.5020 (17) ŵ = 0.10 mm1
c = 14.676 (3) ÅT = 298 K
β = 107.25 (3)°Plate, colorless
V = 1509.0 (5) Å30.20 × 0.10 × 0.10 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
1473 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 25.3°, θmin = 1.7°
ω/2θ scansh = 014
Absorption correction: ψ scan
(North et al., 1968)
k = 010
Tmin = 0.981, Tmax = 0.991l = 1717
2874 measured reflections3 standard reflections every 200 reflections
2732 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.06P)2 + 1.15P]
where P = (Fo2 + 2Fc2)/3
2732 reflections(Δ/σ)max < 0.001
193 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.20 e Å3
0 constraints
Crystal data top
C16H20O5V = 1509.0 (5) Å3
Mr = 292.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.663 (3) ŵ = 0.10 mm1
b = 8.5020 (17) ÅT = 298 K
c = 14.676 (3) Å0.20 × 0.10 × 0.10 mm
β = 107.25 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
1473 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.039
Tmin = 0.981, Tmax = 0.9913 standard reflections every 200 reflections
2874 measured reflections intensity decay: 1%
2732 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.168H-atom parameters constrained
S = 0.93Δρmax = 0.22 e Å3
2732 reflectionsΔρmin = 0.20 e Å3
193 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5800 (2)0.2003 (4)0.7367 (2)0.0809 (10)
C10.7006 (3)0.3398 (5)0.6698 (3)0.0673 (13)
H1A0.74450.34950.73530.101*
H1B0.68230.44260.64280.101*
H1C0.74180.28380.63480.101*
O20.26250 (19)0.0087 (3)0.46428 (15)0.0472 (6)
C20.5977 (3)0.2525 (5)0.6646 (3)0.0522 (10)
O30.27923 (17)0.1243 (3)0.31287 (15)0.0431 (6)
C30.5143 (3)0.2248 (4)0.5700 (2)0.0403 (8)
O40.1020 (2)0.3513 (3)0.20147 (19)0.0602 (8)
C40.4262 (3)0.1219 (4)0.5639 (2)0.0417 (9)
H4A0.41970.07400.61890.050*
C50.3492 (3)0.0907 (4)0.4776 (2)0.0360 (8)
O50.0032 (2)0.2019 (4)0.0853 (2)0.0883 (11)
C60.3593 (3)0.1627 (4)0.3945 (2)0.0375 (8)
C70.4462 (3)0.2622 (4)0.3995 (2)0.0415 (9)
H7A0.45340.30860.34420.050*
C80.5237 (3)0.2938 (4)0.4871 (3)0.0464 (9)
H8A0.58230.36160.49010.056*
C90.2450 (3)0.0810 (5)0.5458 (3)0.0565 (11)
H9A0.18610.15620.52590.085*
H9B0.22560.00220.58490.085*
H9C0.31150.13340.58170.085*
C100.2902 (3)0.1857 (4)0.2248 (2)0.0413 (9)
H10A0.35450.14040.21180.050*
H10B0.29940.29900.22920.050*
C110.1888 (3)0.1450 (4)0.1471 (2)0.0414 (8)
C120.1746 (3)0.0231 (5)0.1132 (3)0.0567 (11)
H12A0.23120.09790.14530.068*
H12B0.10010.06530.09300.068*
C130.2038 (3)0.0959 (5)0.0513 (2)0.0590 (11)
H13A0.14710.12680.00640.071*
H13B0.27840.09420.04610.071*
C140.0850 (3)0.2319 (5)0.1393 (3)0.0497 (10)
C150.0056 (4)0.4466 (6)0.2022 (3)0.0750 (14)
H15A0.06100.38430.17770.090*
H15B0.01130.47560.26750.090*
C160.0033 (4)0.5888 (6)0.1448 (4)0.0806 (14)
H16A0.06610.64900.14850.121*
H16B0.01230.56050.07970.121*
H16C0.06260.65060.16870.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0617 (18)0.131 (3)0.0465 (16)0.0004 (19)0.0099 (14)0.0115 (18)
C10.052 (2)0.071 (3)0.068 (3)0.009 (2)0.001 (2)0.023 (2)
O20.0434 (13)0.0557 (16)0.0413 (13)0.0115 (13)0.0106 (10)0.0021 (12)
C20.048 (2)0.057 (3)0.045 (2)0.007 (2)0.0029 (18)0.015 (2)
O30.0417 (13)0.0481 (15)0.0364 (12)0.0089 (12)0.0065 (10)0.0034 (12)
C30.0379 (19)0.043 (2)0.0363 (18)0.0070 (17)0.0048 (15)0.0084 (17)
O40.0503 (15)0.0526 (17)0.0738 (18)0.0038 (14)0.0125 (13)0.0084 (15)
C40.0370 (18)0.046 (2)0.042 (2)0.0080 (17)0.0112 (15)0.0006 (17)
C50.0375 (18)0.0311 (18)0.0394 (18)0.0050 (16)0.0113 (15)0.0037 (15)
O50.0523 (18)0.089 (2)0.101 (2)0.0043 (17)0.0115 (17)0.026 (2)
C60.0354 (18)0.036 (2)0.0351 (18)0.0015 (16)0.0019 (14)0.0046 (15)
C70.045 (2)0.035 (2)0.044 (2)0.0015 (17)0.0112 (16)0.0007 (17)
C80.041 (2)0.035 (2)0.058 (2)0.0016 (17)0.0063 (17)0.0061 (18)
C90.058 (2)0.061 (3)0.057 (2)0.006 (2)0.0264 (19)0.010 (2)
C100.045 (2)0.041 (2)0.0385 (19)0.0018 (17)0.0129 (15)0.0033 (16)
C110.050 (2)0.037 (2)0.0351 (18)0.0027 (17)0.0087 (15)0.0003 (16)
C120.066 (3)0.043 (2)0.056 (2)0.002 (2)0.0093 (19)0.0094 (19)
C130.071 (3)0.066 (3)0.037 (2)0.005 (2)0.0111 (18)0.005 (2)
C140.042 (2)0.051 (2)0.047 (2)0.0062 (19)0.0001 (18)0.005 (2)
C150.061 (3)0.069 (3)0.102 (4)0.020 (2)0.034 (3)0.010 (3)
C160.060 (3)0.071 (3)0.112 (4)0.007 (3)0.026 (3)0.002 (3)
Geometric parameters (Å, º) top
O1—C21.227 (4)C8—H8A0.9300
C1—C21.482 (5)C9—H9A0.9600
C1—H1A0.9600C9—H9B0.9600
C1—H1B0.9600C9—H9C0.9600
C1—H1C0.9600C10—C111.483 (4)
O2—C51.352 (4)C10—H10A0.9700
O2—C91.419 (4)C10—H10B0.9700
C2—C31.493 (5)C11—C141.482 (5)
O3—C61.360 (3)C11—C121.506 (5)
O3—C101.438 (4)C11—C131.532 (5)
C3—C81.387 (5)C12—C131.478 (5)
C3—C41.399 (5)C12—H12A0.9700
O4—C141.339 (4)C12—H12B0.9700
O4—C151.468 (4)C13—H13A0.9700
C4—C51.376 (4)C13—H13B0.9700
C4—H4A0.9300C15—C161.459 (6)
C5—C61.405 (5)C15—H15A0.9700
O5—C141.189 (4)C15—H15B0.9700
C6—C71.373 (4)C16—H16A0.9600
C7—C81.393 (5)C16—H16B0.9600
C7—H7A0.9300C16—H16C0.9600
C2—C1—H1A109.5C11—C10—H10A110.0
C2—C1—H1B109.5O3—C10—H10B110.0
H1A—C1—H1B109.5C11—C10—H10B110.0
C2—C1—H1C109.5H10A—C10—H10B108.4
H1A—C1—H1C109.5C14—C11—C10119.3 (3)
H1B—C1—H1C109.5C14—C11—C12115.5 (3)
C5—O2—C9118.1 (3)C10—C11—C12117.9 (3)
O1—C2—C1121.3 (3)C14—C11—C13114.4 (3)
O1—C2—C3119.0 (4)C10—C11—C13117.0 (3)
C1—C2—C3119.7 (4)C12—C11—C1358.2 (2)
C6—O3—C10117.3 (2)C13—C12—C1161.7 (2)
C8—C3—C4118.9 (3)C13—C12—H12A117.6
C8—C3—C2121.8 (3)C11—C12—H12A117.6
C4—C3—C2119.3 (3)C13—C12—H12B117.6
C14—O4—C15117.2 (3)C11—C12—H12B117.6
C5—C4—C3120.9 (3)H12A—C12—H12B114.7
C5—C4—H4A119.5C12—C13—C1160.0 (2)
C3—C4—H4A119.5C12—C13—H13A117.8
O2—C5—C4125.3 (3)C11—C13—H13A117.8
O2—C5—C6115.2 (3)C12—C13—H13B117.8
C4—C5—C6119.5 (3)C11—C13—H13B117.8
O3—C6—C7124.9 (3)H13A—C13—H13B114.9
O3—C6—C5115.1 (3)O5—C14—O4123.1 (4)
C7—C6—C5120.0 (3)O5—C14—C11125.5 (4)
C6—C7—C8120.1 (3)O4—C14—C11111.4 (3)
C6—C7—H7A119.9C16—C15—O4112.0 (4)
C8—C7—H7A119.9C16—C15—H15A109.2
C3—C8—C7120.5 (3)O4—C15—H15A109.2
C3—C8—H8A119.7C16—C15—H15B109.2
C7—C8—H8A119.7O4—C15—H15B109.2
O2—C9—H9A109.5H15A—C15—H15B107.9
O2—C9—H9B109.5C15—C16—H16A109.5
H9A—C9—H9B109.5C15—C16—H16B109.5
O2—C9—H9C109.5H16A—C16—H16B109.5
H9A—C9—H9C109.5C15—C16—H16C109.5
H9B—C9—H9C109.5H16A—C16—H16C109.5
O3—C10—C11108.3 (3)H16B—C16—H16C109.5
O3—C10—H10A110.0
O1—C2—C3—C8173.4 (4)C2—C3—C8—C7178.2 (3)
C1—C2—C3—C87.6 (5)C6—C7—C8—C30.3 (5)
O1—C2—C3—C49.0 (5)C6—O3—C10—C11173.7 (3)
C1—C2—C3—C4170.0 (3)O3—C10—C11—C1474.4 (4)
C8—C3—C4—C50.8 (5)O3—C10—C11—C1274.2 (4)
C2—C3—C4—C5178.5 (3)O3—C10—C11—C13140.7 (3)
C9—O2—C5—C43.6 (5)C14—C11—C12—C13104.1 (4)
C9—O2—C5—C6177.7 (3)C10—C11—C12—C13106.1 (4)
C3—C4—C5—O2178.9 (3)C14—C11—C13—C12106.0 (4)
C3—C4—C5—C60.2 (5)C10—C11—C13—C12107.5 (4)
C10—O3—C6—C73.6 (5)C15—O4—C14—O50.7 (6)
C10—O3—C6—C5175.5 (3)C15—O4—C14—C11179.3 (3)
O2—C5—C6—O31.2 (4)C10—C11—C14—O5173.6 (4)
C4—C5—C6—O3179.9 (3)C12—C11—C14—O524.2 (6)
O2—C5—C6—C7178.1 (3)C13—C11—C14—O540.7 (5)
C4—C5—C6—C70.7 (5)C10—C11—C14—O46.4 (5)
O3—C6—C7—C8179.9 (3)C12—C11—C14—O4155.8 (3)
C5—C6—C7—C81.0 (5)C13—C11—C14—O4139.3 (3)
C4—C3—C8—C70.6 (5)C14—O4—C15—C1696.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···O1i0.932.563.329 (4)140
C15—H15A···O50.972.322.678 (6)101
Symmetry code: (i) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC16H20O5
Mr292.32
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)12.663 (3), 8.5020 (17), 14.676 (3)
β (°) 107.25 (3)
V3)1509.0 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.981, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
2874, 2732, 1473
Rint0.039
(sin θ/λ)max1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.168, 0.93
No. of reflections2732
No. of parameters193
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.20

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···O1i0.93002.56003.329 (4)140.00
Symmetry code: (i) x, y+1/2, z1/2.
 

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

First citationChen, G. P. (2008). Advenchen Laboratories, LLC, USA. WO Patent No. 2008112407.
First citationEnraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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