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

Cheng, P.-F.; Wang, C.-J.; Wang, Y.-X.

doi:10.1107/S1600536809038021

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2646

https://doi.org/10.1107/S1600536809038021

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

Peng-Fei Cheng,^a Chao-Jie Wang ^a,^b and Yu-Xia Wang ^a,^b ^*

^aCollege of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, People's Republic of China, and ^bKey Laboratory of Natural Medicine and Immune Engineering, Henan University, Kaifeng 475004, People's Republic of China
^*Correspondence e-mail: hgxywyx@163.com

(Received 18 September 2009; accepted 20 September 2009; online 3 October 2009)

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 ).

Experimental

Crystal data

C₁₁H₁₀BrNO₂
M_r = 268.11
Monoclinic, P 2₁
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 ) 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[F² > 2σ(F²)] = 0.026
wR(F²) = 0.060
S = 1.00
1888 reflections
136 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 763 Friedel pairs
Flack parameter: 0.047 (11)

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

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809038021/hb5110Isup2.hkl

checkCIF report

Comment top

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)°.

Related literature top

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

Experimental top

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%).

Structure description top

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

Computing details top

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

Figures top

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

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

Crystal data top

C₁₁H₁₀BrNO₂	F(000) = 268
M_r = 268.11	D_x = 1.661 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1480 reflections
a = 4.8413 (7) Å	θ = 2.8–24.1°
b = 7.3401 (11) Å	µ = 3.81 mm⁻¹
c = 15.095 (2) Å	T = 296 K
β = 91.729 (3)°	Block, colourless
V = 536.18 (14) Å³	0.37 × 0.35 × 0.29 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	1888 independent reflections
Radiation source: fine-focus sealed tube	1622 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 26.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −5→4
T_min = 0.333, T_max = 0.405	k = −9→8
2879 measured reflections	l = −17→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.060	w = 1/[σ²(F_o²) + (0.0027P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
1888 reflections	Δρ_max = 0.41 e Å⁻³
136 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 763 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.047 (11)

Crystal data top

C₁₁H₁₀BrNO₂	V = 536.18 (14) Å³
M_r = 268.11	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 4.8413 (7) Å	µ = 3.81 mm⁻¹
b = 7.3401 (11) Å	T = 296 K
c = 15.095 (2) Å	0.37 × 0.35 × 0.29 mm
β = 91.729 (3)°

Data collection top

Bruker SMART CCD diffractometer	1888 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1622 reflections with I > 2σ(I)
T_min = 0.333, T_max = 0.405	R_int = 0.018
2879 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.060	Δρ_max = 0.41 e Å⁻³
S = 1.00	Δρ_min = −0.25 e Å⁻³
1888 reflections	Absolute structure: Flack (1983), 763 Friedel pairs
136 parameters	Absolute structure parameter: 0.047 (11)
1 restraint

Special details top

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) top

	x	y	z	U_iso*/U_eq
N1	0.6038 (5)	0.5266 (4)	0.75371 (15)	0.0421 (6)
Br1	0.85905 (7)	−0.00237 (6)	0.598616 (19)	0.06409 (14)
O1	0.9554 (5)	0.4693 (4)	0.85776 (14)	0.0650 (7)
O2	0.2346 (5)	0.6583 (3)	0.67773 (15)	0.0544 (6)
C1	0.6620 (7)	0.2145 (5)	0.5540 (2)	0.0525 (8)
H1A	0.7194	0.2405	0.4943	0.063*
H1B	0.4651	0.1897	0.5513	0.063*
C2	0.7160 (7)	0.3787 (4)	0.61137 (19)	0.0492 (8)
H2A	0.6288	0.4842	0.5838	0.059*
H2B	0.9134	0.4012	0.6154	0.059*
C3	0.6075 (7)	0.3556 (4)	0.7045 (2)	0.0489 (8)
H3A	0.4215	0.3064	0.7004	0.059*
H3B	0.7228	0.2685	0.7368	0.059*
C4	0.4095 (6)	0.6634 (4)	0.7365 (2)	0.0415 (7)
C5	0.4650 (6)	0.8063 (4)	0.80381 (19)	0.0398 (7)
C6	0.3321 (6)	0.9709 (5)	0.8172 (2)	0.0480 (8)
H6A	0.1856	1.0083	0.7803	0.058*
C7	0.4252 (8)	1.0770 (5)	0.8873 (2)	0.0567 (9)
H7A	0.3434	1.1896	0.8971	0.068*
C8	0.6392 (7)	1.0182 (7)	0.94342 (19)	0.0571 (9)
H8A	0.6951	1.0907	0.9912	0.068*
C9	0.7708 (7)	0.8541 (5)	0.9298 (2)	0.0514 (8)
H9A	0.9156	0.8158	0.9672	0.062*
C10	0.6813 (6)	0.7490 (4)	0.85924 (19)	0.0409 (7)
C11	0.7744 (7)	0.5670 (4)	0.82773 (19)	0.0464 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0494 (13)	0.0407 (19)	0.0357 (11)	0.0000 (12)	−0.0045 (10)	−0.0009 (12)
Br1	0.0801 (2)	0.0547 (2)	0.0575 (2)	0.0109 (2)	0.00154 (15)	−0.0067 (3)
O1	0.0724 (15)	0.0709 (18)	0.0506 (11)	0.0190 (15)	−0.0163 (11)	0.0038 (14)
O2	0.0581 (14)	0.0549 (14)	0.0491 (13)	0.0018 (11)	−0.0188 (11)	−0.0052 (11)
C1	0.061 (2)	0.054 (2)	0.0415 (17)	−0.0002 (15)	−0.0124 (16)	0.0022 (15)
C2	0.067 (2)	0.0421 (17)	0.0381 (16)	−0.0027 (15)	−0.0032 (15)	0.0027 (14)
C3	0.066 (2)	0.0390 (18)	0.0416 (16)	0.0025 (15)	−0.0022 (15)	0.0016 (14)
C4	0.0398 (17)	0.0461 (18)	0.0385 (16)	−0.0046 (14)	−0.0016 (14)	0.0050 (13)
C5	0.0417 (16)	0.0461 (17)	0.0316 (14)	−0.0081 (13)	0.0013 (12)	0.0027 (12)
C6	0.0529 (16)	0.048 (2)	0.0428 (14)	−0.0023 (16)	−0.0006 (12)	−0.0015 (17)
C7	0.069 (2)	0.0488 (18)	0.053 (2)	−0.0096 (16)	0.0114 (18)	−0.0059 (15)
C8	0.0614 (19)	0.069 (3)	0.0406 (15)	−0.019 (2)	0.0050 (14)	−0.015 (2)
C9	0.0483 (19)	0.069 (2)	0.0363 (16)	−0.0116 (17)	−0.0025 (15)	0.0002 (16)
C10	0.0424 (16)	0.0505 (17)	0.0300 (14)	−0.0065 (13)	0.0027 (13)	0.0042 (13)
C11	0.0519 (19)	0.0556 (19)	0.0314 (15)	−0.0024 (15)	−0.0024 (14)	0.0040 (13)

Geometric parameters (Å, º) top

N1—C4	1.395 (4)	C3—H3B	0.9700
N1—C11	1.401 (4)	C4—C5	1.479 (4)
N1—C3	1.459 (4)	C5—C10	1.386 (4)
Br1—C1	1.965 (3)	C5—C6	1.387 (5)
O1—C11	1.210 (4)	C6—C7	1.379 (5)
O2—C4	1.208 (3)	C6—H6A	0.9300
C1—C2	1.503 (4)	C7—C8	1.387 (5)
C1—H1A	0.9700	C7—H7A	0.9300
C1—H1B	0.9700	C8—C9	1.381 (6)
C2—C3	1.525 (4)	C8—H8A	0.9300
C2—H2A	0.9700	C9—C10	1.374 (4)
C2—H2B	0.9700	C9—H9A	0.9300
C3—H3A	0.9700	C10—C11	1.492 (4)

C4—N1—C11	112.0 (3)	N1—C4—C5	106.0 (2)
C4—N1—C3	122.9 (2)	C10—C5—C6	121.5 (3)
C11—N1—C3	124.9 (3)	C10—C5—C4	108.5 (3)
C2—C1—Br1	112.2 (2)	C6—C5—C4	130.0 (3)
C2—C1—H1A	109.2	C7—C6—C5	117.5 (3)
Br1—C1—H1A	109.2	C7—C6—H6A	121.3
C2—C1—H1B	109.2	C5—C6—H6A	121.3
Br1—C1—H1B	109.2	C6—C7—C8	120.9 (4)
H1A—C1—H1B	107.9	C6—C7—H7A	119.5
C1—C2—C3	112.6 (3)	C8—C7—H7A	119.5
C1—C2—H2A	109.1	C9—C8—C7	121.3 (3)
C3—C2—H2A	109.1	C9—C8—H8A	119.3
C1—C2—H2B	109.1	C7—C8—H8A	119.3
C3—C2—H2B	109.1	C10—C9—C8	117.9 (3)
H2A—C2—H2B	107.8	C10—C9—H9A	121.0
N1—C3—C2	112.5 (3)	C8—C9—H9A	121.0
N1—C3—H3A	109.1	C9—C10—C5	120.8 (3)
C2—C3—H3A	109.1	C9—C10—C11	131.2 (3)
N1—C3—H3B	109.1	C5—C10—C11	108.0 (3)
C2—C3—H3B	109.1	O1—C11—N1	125.2 (3)
H3A—C3—H3B	107.8	O1—C11—C10	129.3 (3)
O2—C4—N1	124.6 (3)	N1—C11—C10	105.5 (3)
O2—C4—C5	129.4 (3)

Br1—C1—C2—C3	−64.1 (4)	C7—C8—C9—C10	−0.8 (5)
C4—N1—C3—C2	74.3 (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—C9	0.2 (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—C11	179.1 (3)
C11—N1—C4—C5	1.7 (3)	C4—C5—C10—C11	0.9 (3)
C3—N1—C4—C5	176.3 (3)	C4—N1—C11—O1	178.3 (3)
O2—C4—C5—C10	178.1 (3)	C3—N1—C11—O1	3.8 (5)
N1—C4—C5—C10	−1.6 (3)	C4—N1—C11—C10	−1.1 (3)
O2—C4—C5—C6	0.0 (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—C7	0.7 (4)	C5—C10—C11—O1	−179.3 (3)
C4—C5—C6—C7	178.6 (3)	C9—C10—C11—N1	178.9 (3)
C5—C6—C7—C8	−1.7 (5)	C5—C10—C11—N1	0.1 (3)
C6—C7—C8—C9	1.7 (5)

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀BrNO₂
M_r	268.11
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	4.8413 (7), 7.3401 (11), 15.095 (2)
β (°)	91.729 (3)
V (Å³)	536.18 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.81
Crystal size (mm)	0.37 × 0.35 × 0.29

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.333, 0.405
No. of measured, independent and observed [I > 2σ(I)] reflections	2879, 1888, 1622
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.060, 1.00
No. of reflections	1888
No. of parameters	136
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.25
Absolute structure	Flack (1983), 763 Friedel pairs
Absolute structure parameter	0.047 (11)

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Acknowledgements

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

References

Brańa, M. F. & Ramos, A. (2001). Curr. Med. Chem. Anticancer Agents, 1, 237–255. PubMed Google Scholar
Bruker (2001). SAINT-Plus, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar