2-(3-Bromo-prop-yl)isoindoline-1,3-dione.

In the title compound, C(11)H(10)BrNO(2), the dihedral angle between the five- and six-membered rings of the phthalamide system is 1.00 (16)°. There are no significant inter-molecular inter-ations except for van der Waals contacts.

Related literature

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

Experimental

Crystal data

C11H10BrNO2

M = 268.11

Monoclinic,

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[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 ▶), 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.

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

C11H10BrNO2	F(000) = 268
Mr = 268.11	Dx = 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

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

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(Fo2) + (0.0027P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
1888 reflections	Δρmax = 0.41 e Å−3
136 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack (1983), 763 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.047 (11)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)