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

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ISSN: 2056-9890

(E)-2-(4-Chloro­benzyl­­idene)indan-1-one

aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my

(Received 22 June 2011; accepted 9 July 2011; online 16 July 2011)

In the title compound, C16H11ClO, the dihedral angle between the almost planar dihydro­indene ring system (r.m.s. deviation = 0.009 Å) and the chloro­benzene ring is 3.51 (14)°. In the crystal, mol­ecules are connected by C—H⋯O and weak C—H⋯Cl inter­actions, forming infinite layers parallel to (101).

Related literature

For biological background to dihydro­indene derivatives, see: Akritopoulou-Zanze et al. (2007[Akritopoulou-Zanze, I., Albert, D. H., Bousquet, P. F., Cunha, G. A., Harris, C. M., Moskey, M., Dinges, J., Stewart, K. D. & Sowin, T. J. (2007). Bioorg. Med. Chem. Lett. 17, 3136-3140.]); Muhsin et al. (2006[Muhsin, M., Graham, J. & Kirkpatrick, P. (2006). Nat. Rev. Drug Disc. 3, 995-996.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C16H11ClO

  • Mr = 254.70

  • Triclinic, P 1

  • a = 3.8649 (2) Å

  • b = 6.5233 (3) Å

  • c = 12.1703 (6) Å

  • α = 91.374 (4)°

  • β = 95.914 (4)°

  • γ = 103.483 (4)°

  • V = 296.43 (3) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.30 mm−1

  • T = 100 K

  • 0.43 × 0.28 × 0.04 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.882, Tmax = 0.988

  • 3942 measured reflections

  • 2159 independent reflections

  • 2072 reflections with I > 2σ(I)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.124

  • S = 1.06

  • 2159 reflections

  • 163 parameters

  • 3 restraints

  • H-atom parameters constrained

  • Δρmax = 0.63 e Å−3

  • Δρmin = −0.48 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 870 Friedel pairs

  • Flack parameter: 0.05 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C1—H1A⋯O1i 0.99 2.49 3.436 (4) 159
C5—H5A⋯Cl1ii 0.95 2.80 3.591 (4) 141
Symmetry codes: (i) x, y-1, z; (ii) x-1, y+1, z-1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Substituted dihydroindene derivatives have been used as multitargeted kinase inhibitors: Initial efforts focused on the development of selective KDR inhibitors, while later strategies involved the improvement of potency toward multiple kinase targets (Akritopoulou-Zanze et al. 2007). Thus, several dihydroindene derivatives were identified as potent KDR, Flt1, Flt3, and c-Kit inhibitors. Initial strategies involved single target therapies and resulted in the FDA approval of Avastin (a humanized monoclonal antibody targeting VEGF, the growth factor that stimulates VEGFRs) for the treatment of metastatic colorectal cancer (Muhsin et al. 2006). As part of our studies in this area, we now report the synthesis and structure of the title compound, (I).

All parameters in (I) within normal ranges. The dihydroindene ring is almost planar with the maximum deviation of -0.015 (4)Å for atom C7. It make a dihedral angle of 3.51 (14)° with the adjacent benzene ring (Fig. 1). In the crystal, the molecules are interconnected by C—H···O and C—H···Cl interactions (Table 1) to form infinite layers (Fig. 2) parallel to the (101)-plane.

Related literature top

For biological background to dihydroindene derivatives, see: Akritopoulou-Zanze et al. (2007); Muhsin et al. (2006). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 2,3-dihydro-IH-indene-1-one (0.001 mmol) and 4-chlorbenzaldehyde (0.001 mmol) were dissolved in methanol (10 mL) and 30% sodium hydroxide solution (5ml) was added. The solution was stirred for 5 hour. After completion of the reaction as evident from TLC, the mixture was poured into crushed ice then neutralized with Con HCl. The precipitated solid was filtered, washed with water and recrystallised from ethanol to reveal the title compound as light yellow plates of (I).

Refinement top

All H-atoms were positioned geometrically and refined using a riding model, with C-H = 0.95 and 0.99Å, and with Uiso = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure, showing 50% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radius.
[Figure 2] Fig. 2. The packing of (I) viewed along the a axis. Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.
(E)-2-(4-Chlorobenzylidene)indan-1-one top
Crystal data top
C16H11ClOZ = 1
Mr = 254.70F(000) = 132
Triclinic, P1Dx = 1.427 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 3.8649 (2) ÅCell parameters from 2756 reflections
b = 6.5233 (3) Åθ = 3.2–32.1°
c = 12.1703 (6) ŵ = 0.30 mm1
α = 91.374 (4)°T = 100 K
β = 95.914 (4)°Plate, light-yellow
γ = 103.483 (4)°0.43 × 0.28 × 0.04 mm
V = 296.43 (3) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
2159 independent reflections
Radiation source: fine-focus sealed tube2072 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
ϕ and ω scansθmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 44
Tmin = 0.882, Tmax = 0.988k = 88
3942 measured reflectionsl = 1515
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.124 w = 1/[σ2(Fo2) + (0.0685P)2 + 0.1711P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2159 reflectionsΔρmax = 0.63 e Å3
163 parametersΔρmin = 0.48 e Å3
3 restraintsAbsolute structure: Flack (1983), 870 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (8)
Crystal data top
C16H11ClOγ = 103.483 (4)°
Mr = 254.70V = 296.43 (3) Å3
Triclinic, P1Z = 1
a = 3.8649 (2) ÅMo Kα radiation
b = 6.5233 (3) ŵ = 0.30 mm1
c = 12.1703 (6) ÅT = 100 K
α = 91.374 (4)°0.43 × 0.28 × 0.04 mm
β = 95.914 (4)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
2159 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2072 reflections with I > 2σ(I)
Tmin = 0.882, Tmax = 0.988Rint = 0.039
3942 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.124Δρmax = 0.63 e Å3
S = 1.06Δρmin = 0.48 e Å3
2159 reflectionsAbsolute structure: Flack (1983), 870 Friedel pairs
163 parametersAbsolute structure parameter: 0.05 (8)
3 restraints
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl11.33869 (16)0.02880 (10)0.53352 (7)0.0254 (2)
O10.9589 (7)0.8574 (3)0.0177 (2)0.0249 (5)
C10.5969 (8)0.2910 (5)0.0183 (3)0.0179 (7)
H1A0.74200.18820.00460.022*
H1B0.40620.22630.06390.022*
C20.4406 (9)0.3621 (5)0.0892 (3)0.0184 (6)
C30.2093 (9)0.2374 (5)0.1742 (3)0.0194 (7)
H3A0.12940.08930.16830.023*
C40.0999 (9)0.3344 (5)0.2667 (3)0.0226 (7)
H4A0.05720.25120.32480.027*
C50.2154 (10)0.5534 (6)0.2770 (3)0.0239 (7)
H5A0.13580.61750.34100.029*
C60.4483 (9)0.6754 (5)0.1921 (3)0.0221 (7)
H6A0.53220.82310.19830.026*
C70.5554 (9)0.5799 (5)0.0994 (3)0.0196 (7)
C80.8022 (8)0.6717 (5)0.0003 (3)0.0186 (7)
C90.8293 (9)0.4952 (5)0.0738 (3)0.0188 (7)
C101.0366 (9)0.5332 (5)0.1708 (3)0.0195 (7)
H10A1.16490.67580.18560.023*
C111.0966 (8)0.3896 (5)0.2575 (3)0.0177 (7)
C121.3093 (9)0.4750 (5)0.3561 (3)0.0205 (7)
H12A1.40650.62310.36390.025*
C131.3816 (9)0.3519 (6)0.4415 (3)0.0225 (7)
H13A1.52420.41360.50760.027*
C141.2417 (9)0.1354 (5)0.4291 (3)0.0202 (7)
C151.0307 (9)0.0433 (5)0.3330 (3)0.0210 (7)
H15A0.93610.10510.32590.025*
C160.9595 (9)0.1698 (5)0.2477 (3)0.0178 (7)
H16A0.81640.10710.18180.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0283 (4)0.0188 (4)0.0279 (4)0.0036 (3)0.0010 (3)0.0050 (3)
O10.0255 (13)0.0120 (11)0.0341 (13)0.0017 (10)0.0027 (10)0.0018 (9)
C10.0187 (16)0.0079 (13)0.0265 (16)0.0002 (12)0.0066 (13)0.0009 (11)
C20.0165 (16)0.0129 (14)0.0253 (15)0.0011 (13)0.0048 (12)0.0038 (12)
C30.0150 (15)0.0120 (15)0.0273 (17)0.0045 (13)0.0025 (13)0.0001 (12)
C40.0166 (16)0.0209 (16)0.0263 (16)0.0032 (14)0.0017 (13)0.0013 (13)
C50.0201 (17)0.0222 (18)0.0279 (17)0.0004 (14)0.0046 (13)0.0051 (13)
C60.0204 (17)0.0136 (15)0.0311 (18)0.0006 (13)0.0051 (14)0.0042 (12)
C70.0161 (16)0.0139 (15)0.0272 (17)0.0006 (12)0.0052 (13)0.0006 (12)
C80.0148 (15)0.0118 (14)0.0297 (17)0.0024 (12)0.0053 (13)0.0037 (12)
C90.0163 (15)0.0092 (15)0.0293 (17)0.0019 (12)0.0064 (13)0.0006 (12)
C100.0180 (16)0.0102 (14)0.0276 (16)0.0023 (12)0.0031 (13)0.0005 (12)
C110.0146 (16)0.0121 (15)0.0262 (17)0.0021 (12)0.0040 (13)0.0006 (12)
C120.0181 (16)0.0131 (15)0.0283 (17)0.0003 (13)0.0015 (13)0.0033 (12)
C130.0171 (17)0.0207 (17)0.0273 (18)0.0001 (14)0.0025 (14)0.0039 (14)
C140.0159 (17)0.0200 (17)0.0251 (17)0.0037 (13)0.0039 (13)0.0088 (13)
C150.0209 (18)0.0147 (16)0.0270 (18)0.0031 (14)0.0030 (14)0.0017 (13)
C160.0165 (16)0.0111 (15)0.0232 (17)0.0012 (13)0.0014 (13)0.0000 (12)
Geometric parameters (Å, º) top
Cl1—C141.749 (3)C7—C81.478 (5)
O1—C81.225 (4)C8—C91.495 (4)
C1—C21.513 (5)C9—C101.340 (5)
C1—C91.520 (4)C10—C111.464 (5)
C1—H1A0.9900C10—H10A0.9500
C1—H1B0.9900C11—C121.405 (4)
C2—C71.399 (4)C11—C161.406 (4)
C2—C31.400 (4)C12—C131.375 (5)
C3—C41.382 (5)C12—H12A0.9500
C3—H3A0.9500C13—C141.388 (5)
C4—C51.407 (5)C13—H13A0.9500
C4—H4A0.9500C14—C151.391 (5)
C5—C61.395 (5)C15—C161.386 (5)
C5—H5A0.9500C15—H15A0.9500
C6—C71.375 (5)C16—H16A0.9500
C6—H6A0.9500
C2—C1—C9103.1 (3)C7—C8—C9107.3 (3)
C2—C1—H1A111.2C10—C9—C8120.3 (3)
C9—C1—H1A111.2C10—C9—C1131.1 (3)
C2—C1—H1B111.2C8—C9—C1108.5 (3)
C9—C1—H1B111.2C9—C10—C11130.2 (3)
H1A—C1—H1B109.1C9—C10—H10A114.9
C7—C2—C3119.8 (3)C11—C10—H10A114.9
C7—C2—C1112.3 (3)C12—C11—C16117.6 (3)
C3—C2—C1127.8 (3)C12—C11—C10118.4 (3)
C4—C3—C2118.6 (3)C16—C11—C10124.0 (3)
C4—C3—H3A120.7C13—C12—C11122.4 (3)
C2—C3—H3A120.7C13—C12—H12A118.8
C3—C4—C5121.6 (3)C11—C12—H12A118.8
C3—C4—H4A119.2C12—C13—C14118.5 (3)
C5—C4—H4A119.2C12—C13—H13A120.8
C6—C5—C4119.2 (3)C14—C13—H13A120.8
C6—C5—H5A120.4C13—C14—C15121.3 (3)
C4—C5—H5A120.4C13—C14—Cl1120.2 (2)
C7—C6—C5119.4 (3)C15—C14—Cl1118.5 (3)
C7—C6—H6A120.3C16—C15—C14119.5 (3)
C5—C6—H6A120.3C16—C15—H15A120.3
C6—C7—C2121.3 (3)C14—C15—H15A120.3
C6—C7—C8129.9 (3)C15—C16—C11120.7 (3)
C2—C7—C8108.7 (3)C15—C16—H16A119.6
O1—C8—C7126.5 (3)C11—C16—H16A119.6
O1—C8—C9126.1 (3)
C9—C1—C2—C70.5 (4)O1—C8—C9—C1178.8 (3)
C9—C1—C2—C3178.9 (3)C7—C8—C9—C10.6 (3)
C7—C2—C3—C40.0 (5)C2—C1—C9—C10179.6 (3)
C1—C2—C3—C4179.4 (3)C2—C1—C9—C80.1 (3)
C2—C3—C4—C50.0 (5)C8—C9—C10—C11177.9 (3)
C3—C4—C5—C60.5 (5)C1—C9—C10—C112.6 (6)
C4—C5—C6—C71.1 (5)C9—C10—C11—C12175.1 (3)
C5—C6—C7—C21.2 (5)C9—C10—C11—C166.1 (6)
C5—C6—C7—C8178.7 (3)C16—C11—C12—C130.7 (5)
C3—C2—C7—C60.6 (5)C10—C11—C12—C13179.6 (3)
C1—C2—C7—C6178.9 (3)C11—C12—C13—C140.7 (5)
C3—C2—C7—C8178.6 (3)C12—C13—C14—C150.4 (5)
C1—C2—C7—C80.9 (4)C12—C13—C14—Cl1177.8 (3)
C6—C7—C8—O10.7 (5)C13—C14—C15—C160.3 (5)
C2—C7—C8—O1178.5 (3)Cl1—C14—C15—C16178.0 (3)
C6—C7—C8—C9178.6 (3)C14—C15—C16—C110.3 (5)
C2—C7—C8—C90.9 (4)C12—C11—C16—C150.5 (5)
O1—C8—C9—C100.8 (5)C10—C11—C16—C15179.3 (3)
C7—C8—C9—C10179.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O1i0.992.493.436 (4)159
C5—H5A···Cl1ii0.952.803.591 (4)141
Symmetry codes: (i) x, y1, z; (ii) x1, y+1, z1.

Experimental details

Crystal data
Chemical formulaC16H11ClO
Mr254.70
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)3.8649 (2), 6.5233 (3), 12.1703 (6)
α, β, γ (°)91.374 (4), 95.914 (4), 103.483 (4)
V3)296.43 (3)
Z1
Radiation typeMo Kα
µ (mm1)0.30
Crystal size (mm)0.43 × 0.28 × 0.04
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.882, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
3942, 2159, 2072
Rint0.039
(sin θ/λ)max1)0.638
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.124, 1.06
No. of reflections2159
No. of parameters163
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.63, 0.48
Absolute structureFlack (1983), 870 Friedel pairs
Absolute structure parameter0.05 (8)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O1i0.992.493.436 (4)159
C5—H5A···Cl1ii0.952.803.591 (4)141
Symmetry codes: (i) x, y1, z; (ii) x1, y+1, z1.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors wish to express their thanks to Universiti Sains Malaysia (USM), Penang, Malaysia for providing research facilities. HKF also thanks USM for the Research University Grant (No. 1001/PFIZIK/811160).

References

First citationAkritopoulou-Zanze, I., Albert, D. H., Bousquet, P. F., Cunha, G. A., Harris, C. M., Moskey, M., Dinges, J., Stewart, K. D. & Sowin, T. J. (2007). Bioorg. Med. Chem. Lett. 17, 3136–3140.  PubMed CAS
First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals
First citationMuhsin, M., Graham, J. & Kirkpatrick, P. (2006). Nat. Rev. Drug Disc. 3, 995–996.  Web of Science CrossRef
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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