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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2646.
Published online 2009 October 3. doi:  10.1107/S1600536809038021
PMCID: PMC2971232

2-(3-Bromo­prop­yl)isoindoline-1,3-dione

Abstract

In the title compound, C11H10BrNO2, the dihedral angle between the five- and six-membered rings of the phthalamide system is 1.00 (16)°. There are no significant inter­molecular inter­ations except for van der Waals contacts.

Related literature

For pharmacological background on phthalamides, see: Brańa & Ramos (2001 [triangle]).

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Object name is e-65-o2646-scheme1.jpg

Experimental

Crystal data

  • C11H10BrNO2
  • M r = 268.11
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2646-efi1.jpg
  • a = 4.8413 (7) Å
  • b = 7.3401 (11) Å
  • c = 15.095 (2) Å
  • β = 91.729 (3)°
  • V = 536.18 (14) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 3.81 mm−1
  • T = 296 K
  • 0.37 × 0.35 × 0.29 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.333, T max = 0.405
  • 2879 measured reflections
  • 1888 independent reflections
  • 1622 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.026
  • wR(F 2) = 0.060
  • S = 1.00
  • 1888 reflections
  • 136 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.25 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 763 Friedel pairs
  • Flack parameter: 0.047 (11)

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809038021/hb5110sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038021/hb5110Isup2.hkl

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

Acknowledgments

This work was supported by the Basic Research Foundation for Natural Science of Henan University.

supplementary crystallographic information

Comment

Phthalimides are well known cytotoxic DNA intercalating agents and have shown promise as potential anti-cancer agents (e.g. Brańa & Ramos, 2001). Its derivatives, such as bis-naphthalimides etc, represent a promising group of DNA-targeted anticancer agents, and the search for more potent analogues remains a priority. We now report the crystal structure of the title compound, (I).

As shown in Fig.1, the title compound consists of a phthalimide group supporting a bromopropane group. In the structure of (I), C11–O1 [1.210 (4) Å] and C4–O2 [1.208 (3) Å] are typical for a C==O double bond, the S(5) ring of N1/C4/C5/C10/C11 and the aromatic ring is approximatively coplanear, characterized by a dihedral angle of 1.00 (16)°.

Experimental

To a mixture of 1,3-dibromopropane (46 ml, 0.45 mol) and acetone (100 ml), potassium phthalimide (22.7 g, 0.15 mol) was added in batches with refluxing. After stirring for additional 12 h, the solid was filtered off, the solvent evaporated in vacuo. The residue was recrystallized in ethanol: evaporation gave (I) as colourless blocks (25.45 g, 63.4%).

Refinement

H atoms were placed geometrically with C—H = 0.93–0.97Å, and refined as riding with Uiso(H)=1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C11H10BrNO2F(000) = 268
Mr = 268.11Dx = 1.661 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1480 reflections
a = 4.8413 (7) Åθ = 2.8–24.1°
b = 7.3401 (11) ŵ = 3.81 mm1
c = 15.095 (2) ÅT = 296 K
β = 91.729 (3)°Block, colourless
V = 536.18 (14) Å30.37 × 0.35 × 0.29 mm
Z = 2

Data collection

Bruker SMART CCD diffractometer1888 independent reflections
Radiation source: fine-focus sealed tube1622 reflections with I > 2σ(I)
graphiteRint = 0.018
ω scansθmax = 26.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −5→4
Tmin = 0.333, Tmax = 0.405k = −9→8
2879 measured reflectionsl = −17→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.060w = 1/[σ2(Fo2) + (0.0027P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
1888 reflectionsΔρmax = 0.41 e Å3
136 parametersΔρmin = −0.25 e Å3
1 restraintAbsolute structure: Flack (1983), 763 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.047 (11)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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)

xyzUiso*/Ueq
N10.6038 (5)0.5266 (4)0.75371 (15)0.0421 (6)
Br10.85905 (7)−0.00237 (6)0.598616 (19)0.06409 (14)
O10.9554 (5)0.4693 (4)0.85776 (14)0.0650 (7)
O20.2346 (5)0.6583 (3)0.67773 (15)0.0544 (6)
C10.6620 (7)0.2145 (5)0.5540 (2)0.0525 (8)
H1A0.71940.24050.49430.063*
H1B0.46510.18970.55130.063*
C20.7160 (7)0.3787 (4)0.61137 (19)0.0492 (8)
H2A0.62880.48420.58380.059*
H2B0.91340.40120.61540.059*
C30.6075 (7)0.3556 (4)0.7045 (2)0.0489 (8)
H3A0.42150.30640.70040.059*
H3B0.72280.26850.73680.059*
C40.4095 (6)0.6634 (4)0.7365 (2)0.0415 (7)
C50.4650 (6)0.8063 (4)0.80381 (19)0.0398 (7)
C60.3321 (6)0.9709 (5)0.8172 (2)0.0480 (8)
H6A0.18561.00830.78030.058*
C70.4252 (8)1.0770 (5)0.8873 (2)0.0567 (9)
H7A0.34341.18960.89710.068*
C80.6392 (7)1.0182 (7)0.94342 (19)0.0571 (9)
H8A0.69511.09070.99120.068*
C90.7708 (7)0.8541 (5)0.9298 (2)0.0514 (8)
H9A0.91560.81580.96720.062*
C100.6813 (6)0.7490 (4)0.85924 (19)0.0409 (7)
C110.7744 (7)0.5670 (4)0.82773 (19)0.0464 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0494 (13)0.0407 (19)0.0357 (11)0.0000 (12)−0.0045 (10)−0.0009 (12)
Br10.0801 (2)0.0547 (2)0.0575 (2)0.0109 (2)0.00154 (15)−0.0067 (3)
O10.0724 (15)0.0709 (18)0.0506 (11)0.0190 (15)−0.0163 (11)0.0038 (14)
O20.0581 (14)0.0549 (14)0.0491 (13)0.0018 (11)−0.0188 (11)−0.0052 (11)
C10.061 (2)0.054 (2)0.0415 (17)−0.0002 (15)−0.0124 (16)0.0022 (15)
C20.067 (2)0.0421 (17)0.0381 (16)−0.0027 (15)−0.0032 (15)0.0027 (14)
C30.066 (2)0.0390 (18)0.0416 (16)0.0025 (15)−0.0022 (15)0.0016 (14)
C40.0398 (17)0.0461 (18)0.0385 (16)−0.0046 (14)−0.0016 (14)0.0050 (13)
C50.0417 (16)0.0461 (17)0.0316 (14)−0.0081 (13)0.0013 (12)0.0027 (12)
C60.0529 (16)0.048 (2)0.0428 (14)−0.0023 (16)−0.0006 (12)−0.0015 (17)
C70.069 (2)0.0488 (18)0.053 (2)−0.0096 (16)0.0114 (18)−0.0059 (15)
C80.0614 (19)0.069 (3)0.0406 (15)−0.019 (2)0.0050 (14)−0.015 (2)
C90.0483 (19)0.069 (2)0.0363 (16)−0.0116 (17)−0.0025 (15)0.0002 (16)
C100.0424 (16)0.0505 (17)0.0300 (14)−0.0065 (13)0.0027 (13)0.0042 (13)
C110.0519 (19)0.0556 (19)0.0314 (15)−0.0024 (15)−0.0024 (14)0.0040 (13)

Geometric parameters (Å, °)

N1—C41.395 (4)C3—H3B0.9700
N1—C111.401 (4)C4—C51.479 (4)
N1—C31.459 (4)C5—C101.386 (4)
Br1—C11.965 (3)C5—C61.387 (5)
O1—C111.210 (4)C6—C71.379 (5)
O2—C41.208 (3)C6—H6A0.9300
C1—C21.503 (4)C7—C81.387 (5)
C1—H1A0.9700C7—H7A0.9300
C1—H1B0.9700C8—C91.381 (6)
C2—C31.525 (4)C8—H8A0.9300
C2—H2A0.9700C9—C101.374 (4)
C2—H2B0.9700C9—H9A0.9300
C3—H3A0.9700C10—C111.492 (4)
C4—N1—C11112.0 (3)N1—C4—C5106.0 (2)
C4—N1—C3122.9 (2)C10—C5—C6121.5 (3)
C11—N1—C3124.9 (3)C10—C5—C4108.5 (3)
C2—C1—Br1112.2 (2)C6—C5—C4130.0 (3)
C2—C1—H1A109.2C7—C6—C5117.5 (3)
Br1—C1—H1A109.2C7—C6—H6A121.3
C2—C1—H1B109.2C5—C6—H6A121.3
Br1—C1—H1B109.2C6—C7—C8120.9 (4)
H1A—C1—H1B107.9C6—C7—H7A119.5
C1—C2—C3112.6 (3)C8—C7—H7A119.5
C1—C2—H2A109.1C9—C8—C7121.3 (3)
C3—C2—H2A109.1C9—C8—H8A119.3
C1—C2—H2B109.1C7—C8—H8A119.3
C3—C2—H2B109.1C10—C9—C8117.9 (3)
H2A—C2—H2B107.8C10—C9—H9A121.0
N1—C3—C2112.5 (3)C8—C9—H9A121.0
N1—C3—H3A109.1C9—C10—C5120.8 (3)
C2—C3—H3A109.1C9—C10—C11131.2 (3)
N1—C3—H3B109.1C5—C10—C11108.0 (3)
C2—C3—H3B109.1O1—C11—N1125.2 (3)
H3A—C3—H3B107.8O1—C11—C10129.3 (3)
O2—C4—N1124.6 (3)N1—C11—C10105.5 (3)
O2—C4—C5129.4 (3)
Br1—C1—C2—C3−64.1 (4)C7—C8—C9—C10−0.8 (5)
C4—N1—C3—C274.3 (4)C8—C9—C10—C5−0.2 (5)
C11—N1—C3—C2−111.8 (3)C8—C9—C10—C11−178.9 (3)
C1—C2—C3—N1−167.3 (3)C6—C5—C10—C90.2 (4)
C11—N1—C4—O2−178.0 (3)C4—C5—C10—C9−178.1 (3)
C3—N1—C4—O2−3.4 (5)C6—C5—C10—C11179.1 (3)
C11—N1—C4—C51.7 (3)C4—C5—C10—C110.9 (3)
C3—N1—C4—C5176.3 (3)C4—N1—C11—O1178.3 (3)
O2—C4—C5—C10178.1 (3)C3—N1—C11—O13.8 (5)
N1—C4—C5—C10−1.6 (3)C4—N1—C11—C10−1.1 (3)
O2—C4—C5—C60.0 (5)C3—N1—C11—C10−175.6 (3)
N1—C4—C5—C6−179.6 (3)C9—C10—C11—O1−0.5 (5)
C10—C5—C6—C70.7 (4)C5—C10—C11—O1−179.3 (3)
C4—C5—C6—C7178.6 (3)C9—C10—C11—N1178.9 (3)
C5—C6—C7—C8−1.7 (5)C5—C10—C11—N10.1 (3)
C6—C7—C8—C91.7 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5110).

References

  • Brańa, M. F. & Ramos, A. (2001). Curr. Med. Chem. Anticancer Agents, 1, 237–255. [PubMed]
  • Bruker (2001). SAINT-Plus, SMART and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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