6-Bromo-1-butylindoline-2,3-dione.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(12)H(12)BrNO(2). The C-C bond lengths of the two carbonyl C atoms of the five-membered rings are distinctly longer than a normal Csp(2)-Csp(2) single bond. One of the mol-ecules makes parallel self-coupled (inversion) dimers by π-π inter-actions with phen-yl-phenyl inter-planar distances of 3.403 (2) Å. The other mol-ecule also forms self-dimers at longer phen-yl-phenyl plane distances [3.649 (2) Å]. In the crystal, a C-H⋯O interaction is seen.

Related literature

For synthesis and applications, see: Kopka et al. (2006 ▶); Pirrung et al. (2005 ▶); Zhou et al. (2006 ▶). For related crystal structures, see: Goldschmidt & Llewellyn (1950 ▶); Palenik et al. (1990 ▶).

Experimental

Crystal data

C12H12BrNO2

M = 282.14

Monoclinic,

a = 13.3097 (2) Å

b = 11.8793 (2) Å

c = 16.2238 (2) Å

β = 112.340 (1)°

V = 2372.62 (6) Å3

Z = 8

Mo Kα radiation

μ = 3.45 mm−1

T = 296 (2) K

0.37 × 0.13 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.526, T max = 0.744 (expected range = 0.487–0.689)

16713 measured reflections

5170 independent reflections

2424 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.070

S = 0.93

5170 reflections

364 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042098/cs2100sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042098/cs2100Isup2.hkl

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

C12H12BrNO2	F(000) = 1136
Mr = 282.14	Dx = 1.580 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3677 reflections
a = 13.3097 (2) Å	θ = 2.2–23.8°
b = 11.8793 (2) Å	µ = 3.45 mm−1
c = 16.2238 (2) Å	T = 296 K
β = 112.340 (1)°	Plank, orange
V = 2372.62 (6) Å3	0.37 × 0.13 × 0.11 mm
Z = 8

Bruker APEXII CCD diffractometer	5170 independent reflections
Radiation source: fine-focus sealed tube	2424 reflections with I > 2σ(I)
graphite	Rint = 0.076
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 1.7°
phi and ω scans	h = −16→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→10
Tmin = 0.526, Tmax = 0.744	l = −20→20
16713 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.070	w = 1/[σ2(Fo2) + (0.0158P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max = 0.001
5170 reflections	Δρmax = 0.39 e Å−3
364 parameters	Δρmin = −0.49 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00147 (12)

	x	y	z	Uiso*/Ueq
Br1	0.25474 (2)	0.52247 (4)	0.03130 (3)	0.07546 (17)
O1	0.82928 (15)	0.3064 (2)	0.18511 (13)	0.0649 (7)
O2	0.82426 (16)	0.5497 (2)	0.22161 (15)	0.0682 (7)
N1	0.64300 (18)	0.3303 (3)	0.12570 (15)	0.0448 (7)
C1	0.7490 (2)	0.3648 (3)	0.1675 (2)	0.0477 (9)
C2	0.7445 (2)	0.4919 (3)	0.18633 (19)	0.0475 (9)
C3	0.6286 (2)	0.5203 (3)	0.15321 (19)	0.0431 (9)
C4	0.5754 (3)	0.6195 (4)	0.1517 (2)	0.0519 (10)
H4	0.616 (2)	0.688 (3)	0.1810 (18)	0.058 (10)*
C5	0.4628 (3)	0.6193 (4)	0.1150 (2)	0.0535 (10)
H5	0.4240 (19)	0.690 (3)	0.1167 (16)	0.047 (9)*
C6	0.4095 (2)	0.5211 (4)	0.0815 (2)	0.0476 (9)
C7	0.4595 (2)	0.4196 (4)	0.0807 (2)	0.0435 (9)
H7	0.4227 (18)	0.351 (2)	0.0576 (16)	0.036 (9)*
C8	0.5720 (2)	0.4213 (3)	0.11826 (18)	0.0382 (8)
C9	0.6102 (3)	0.2182 (3)	0.0965 (3)	0.0504 (10)
H9A	0.538 (2)	0.218 (3)	0.040 (2)	0.073 (10)*
H9B	0.659 (2)	0.185 (3)	0.081 (2)	0.078 (13)*
C10	0.5921 (3)	0.1458 (4)	0.1651 (3)	0.0640 (11)
H10B	0.537 (2)	0.185 (2)	0.1859 (17)	0.052 (9)*
H10A	0.658 (2)	0.147 (3)	0.221 (2)	0.070 (11)*
C11	0.5557 (4)	0.0275 (4)	0.1272 (3)	0.0831 (14)
H11A	0.613 (3)	−0.012 (3)	0.121 (2)	0.100*
H11B	0.477 (3)	0.032 (3)	0.085 (2)	0.100*
C12	0.5496 (3)	−0.0541 (4)	0.1927 (3)	0.1061 (15)
H12A	0.6201	−0.0628	0.2392	0.138 (10)*
H12B	0.5253	−0.1253	0.1641	0.138 (10)*
H12C	0.4993	−0.0276	0.2179	0.138 (10)*
Br2	0.25658 (2)	−0.10901 (4)	0.09621 (3)	0.07726 (17)
O3	−0.32733 (16)	−0.1957 (2)	0.03877 (14)	0.0728 (8)
O4	−0.30063 (18)	−0.2190 (2)	−0.13304 (15)	0.0795 (8)
N2	−0.14314 (18)	−0.1581 (2)	0.08915 (16)	0.0493 (7)
C21	−0.2438 (3)	−0.1837 (3)	0.0266 (2)	0.0550 (10)
C22	−0.2278 (3)	−0.1969 (3)	−0.0632 (2)	0.0538 (9)
C23	−0.1117 (2)	−0.1769 (3)	−0.0404 (2)	0.0446 (8)
C24	−0.0483 (3)	−0.1808 (3)	−0.0900 (3)	0.0552 (10)
H24	−0.084 (2)	−0.193 (3)	−0.1480 (19)	0.060 (11)*
C25	0.0612 (3)	−0.1618 (3)	−0.0495 (3)	0.0599 (10)
H25	0.1067 (18)	−0.164 (2)	−0.0805 (16)	0.035 (8)*
C26	0.1047 (2)	−0.1379 (3)	0.0399 (2)	0.0513 (9)
C27	0.0439 (2)	−0.1332 (3)	0.0925 (2)	0.0501 (10)
H27	0.0727 (17)	−0.120 (2)	0.1503 (16)	0.034 (9)*
C28	−0.0653 (2)	−0.1544 (3)	0.0505 (2)	0.0443 (8)
C29	−0.1191 (3)	−0.1497 (4)	0.1850 (2)	0.0545 (11)
H29A	−0.1731 (19)	−0.188 (2)	0.1991 (16)	0.045 (9)*
H29B	−0.056 (2)	−0.198 (3)	0.2144 (19)	0.068 (11)*
C30	−0.1031 (3)	−0.0315 (4)	0.2208 (3)	0.0592 (11)
H30B	−0.049 (2)	0.010 (3)	0.200 (2)	0.077 (11)*
H30A	−0.162 (2)	0.016 (3)	0.195 (2)	0.067 (12)*
C31	−0.0728 (4)	−0.0318 (4)	0.3219 (3)	0.0771 (13)
H31B	−0.002 (3)	−0.071 (3)	0.355 (2)	0.112 (17)*
H31A	−0.133 (3)	−0.073 (3)	0.333 (2)	0.103 (14)*
C32	−0.0463 (3)	0.0819 (4)	0.3617 (2)	0.0941 (14)
H32A	0.0122	0.1132	0.3483	0.129 (9)*
H32B	−0.0249	0.0766	0.4252	0.129 (9)*
H32C	−0.1090	0.1295	0.3376	0.129 (9)*

	U11	U22	U33	U12	U13	U23
Br1	0.03753 (19)	0.1118 (4)	0.0741 (3)	0.0122 (2)	0.01790 (17)	0.0168 (3)
O1	0.0405 (12)	0.082 (2)	0.0631 (16)	0.0147 (13)	0.0090 (11)	−0.0007 (14)
O2	0.0450 (13)	0.081 (2)	0.0662 (16)	−0.0181 (13)	0.0076 (12)	−0.0127 (15)
N1	0.0369 (14)	0.046 (2)	0.0473 (17)	−0.0027 (15)	0.0110 (12)	−0.0079 (17)
C1	0.0397 (19)	0.060 (3)	0.039 (2)	−0.0006 (19)	0.0107 (16)	0.001 (2)
C2	0.0372 (17)	0.062 (3)	0.038 (2)	−0.0066 (19)	0.0086 (15)	0.003 (2)
C3	0.0376 (17)	0.049 (3)	0.038 (2)	−0.0040 (19)	0.0091 (15)	−0.005 (2)
C4	0.056 (2)	0.045 (3)	0.051 (2)	−0.007 (2)	0.0165 (18)	−0.006 (2)
C5	0.053 (2)	0.051 (3)	0.056 (2)	0.010 (2)	0.0202 (19)	0.002 (2)
C6	0.0317 (16)	0.069 (3)	0.039 (2)	0.006 (2)	0.0095 (15)	0.005 (2)
C7	0.0361 (18)	0.049 (3)	0.042 (2)	−0.008 (2)	0.0114 (16)	−0.003 (2)
C8	0.0375 (17)	0.044 (2)	0.0305 (18)	0.0009 (18)	0.0100 (14)	0.0031 (18)
C9	0.052 (2)	0.043 (3)	0.053 (3)	0.005 (2)	0.016 (2)	−0.007 (2)
C10	0.072 (3)	0.050 (3)	0.064 (3)	−0.009 (2)	0.019 (2)	−0.004 (3)
C11	0.087 (3)	0.075 (4)	0.077 (3)	−0.005 (3)	0.020 (3)	0.003 (3)
C12	0.121 (4)	0.080 (4)	0.107 (4)	−0.018 (3)	0.032 (3)	−0.006 (4)
Br2	0.0453 (2)	0.0909 (4)	0.0969 (3)	0.0008 (2)	0.0285 (2)	−0.0097 (3)
O3	0.0427 (12)	0.090 (2)	0.0790 (17)	−0.0143 (13)	0.0160 (12)	−0.0119 (15)
O4	0.0672 (15)	0.094 (2)	0.0514 (16)	−0.0202 (15)	−0.0066 (13)	−0.0106 (16)
N2	0.0385 (14)	0.070 (2)	0.0342 (16)	−0.0056 (14)	0.0078 (12)	−0.0067 (16)
C21	0.048 (2)	0.059 (3)	0.049 (2)	−0.008 (2)	0.0089 (18)	−0.010 (2)
C22	0.055 (2)	0.042 (3)	0.052 (2)	−0.0093 (19)	0.0065 (18)	−0.004 (2)
C23	0.0489 (19)	0.043 (2)	0.036 (2)	−0.0037 (17)	0.0100 (17)	−0.0023 (19)
C24	0.072 (3)	0.050 (3)	0.036 (2)	−0.003 (2)	0.012 (2)	−0.003 (2)
C25	0.069 (3)	0.063 (3)	0.059 (3)	0.007 (2)	0.036 (2)	0.003 (2)
C26	0.0444 (18)	0.050 (3)	0.057 (2)	0.0006 (17)	0.0175 (18)	−0.001 (2)
C27	0.0423 (19)	0.064 (3)	0.038 (2)	0.0006 (18)	0.0095 (18)	−0.006 (2)
C28	0.0395 (17)	0.050 (2)	0.038 (2)	−0.0023 (16)	0.0089 (16)	−0.0028 (19)
C29	0.048 (2)	0.070 (3)	0.048 (2)	−0.007 (2)	0.0202 (19)	−0.004 (2)
C30	0.057 (2)	0.064 (3)	0.058 (3)	−0.006 (2)	0.023 (2)	−0.008 (3)
C31	0.103 (4)	0.076 (4)	0.065 (3)	−0.021 (3)	0.046 (3)	−0.020 (3)
C32	0.116 (3)	0.101 (4)	0.076 (3)	−0.027 (3)	0.048 (2)	−0.029 (3)

Br1—C6	1.906 (3)	Br2—C26	1.907 (3)
O1—C1	1.214 (3)	O3—C21	1.209 (3)
O2—C2	1.210 (3)	O4—C22	1.208 (3)
N1—C1	1.375 (3)	N2—C21	1.373 (3)
N1—C8	1.411 (4)	N2—C28	1.401 (3)
N1—C9	1.425 (4)	N2—C29	1.467 (4)
C1—C2	1.545 (4)	C21—C22	1.558 (4)
C2—C3	1.468 (4)	C22—C23	1.465 (4)
C3—C4	1.370 (4)	C23—C24	1.370 (4)
C3—C8	1.395 (4)	C23—C28	1.391 (4)
C4—C5	1.387 (4)	C24—C25	1.371 (4)
C4—H4	0.99 (3)	C24—H24	0.89 (3)
C5—C6	1.366 (4)	C25—C26	1.372 (4)
C5—H5	1.00 (3)	C25—H25	0.92 (2)
C6—C7	1.379 (4)	C26—C27	1.382 (4)
C7—C8	1.386 (4)	C27—C28	1.374 (4)
C7—H7	0.95 (3)	C27—H27	0.88 (2)
C9—C10	1.496 (5)	C29—C30	1.503 (5)
C9—H9A	1.05 (3)	C29—H29A	0.95 (3)
C9—H9B	0.87 (3)	C29—H29B	0.98 (3)
C10—C11	1.536 (6)	C30—C31	1.532 (5)
C10—H10B	1.03 (3)	C30—H30B	1.04 (3)
C10—H10A	0.99 (3)	C30—H30A	0.93 (3)
C11—C12	1.464 (6)	C31—C32	1.481 (5)
C11—H11A	0.94 (4)	C31—H31B	1.00 (4)
C11—H11B	1.01 (3)	C31—H31A	1.01 (4)
C12—H12A	0.9600	C32—H32A	0.9600
C12—H12B	0.9600	C32—H32B	0.9600
C12—H12C	0.9600	C32—H32C	0.9600
C1—N1—C8	110.0 (3)	C21—N2—C28	110.9 (2)
C1—N1—C9	124.8 (3)	C21—N2—C29	123.9 (3)
C8—N1—C9	125.3 (3)	C28—N2—C29	124.9 (2)
O1—C1—N1	126.3 (3)	O3—C21—N2	127.2 (3)
O1—C1—C2	127.4 (3)	O3—C21—C22	127.0 (3)
N1—C1—C2	106.3 (3)	N2—C21—C22	105.7 (3)
O2—C2—C3	130.8 (4)	O4—C22—C23	131.7 (3)
O2—C2—C1	123.8 (3)	O4—C22—C21	123.5 (3)
C3—C2—C1	105.5 (3)	C23—C22—C21	104.7 (3)
C4—C3—C8	121.5 (3)	C24—C23—C28	120.3 (3)
C4—C3—C2	132.0 (3)	C24—C23—C22	132.2 (3)
C8—C3—C2	106.5 (3)	C28—C23—C22	107.4 (3)
C3—C4—C5	118.2 (4)	C23—C24—C25	119.6 (3)
C3—C4—H4	120.7 (16)	C23—C24—H24	115.6 (18)
C5—C4—H4	120.8 (16)	C25—C24—H24	124.7 (19)
C6—C5—C4	119.1 (4)	C24—C25—C26	119.0 (3)
C6—C5—H5	122.6 (15)	C24—C25—H25	122.3 (15)
C4—C5—H5	118.3 (15)	C26—C25—H25	118.7 (15)
C5—C6—C7	124.8 (3)	C25—C26—C27	123.4 (3)
C5—C6—Br1	118.4 (3)	C25—C26—Br2	119.2 (3)
C7—C6—Br1	116.8 (3)	C27—C26—Br2	117.4 (3)
C6—C7—C8	115.3 (3)	C28—C27—C26	116.3 (3)
C6—C7—H7	125.2 (15)	C28—C27—H27	120.7 (16)
C8—C7—H7	119.5 (15)	C26—C27—H27	123.0 (16)
C7—C8—C3	121.1 (3)	C27—C28—C23	121.4 (3)
C7—C8—N1	127.1 (3)	C27—C28—N2	127.3 (3)
C3—C8—N1	111.8 (3)	C23—C28—N2	111.3 (2)
N1—C9—C10	113.9 (3)	N2—C29—C30	114.5 (3)
N1—C9—H9A	110.8 (17)	N2—C29—H29A	110.0 (15)
C10—C9—H9A	107.0 (17)	C30—C29—H29A	111.5 (17)
N1—C9—H9B	111 (2)	N2—C29—H29B	106.1 (17)
C10—C9—H9B	108 (2)	C30—C29—H29B	112.8 (18)
H9A—C9—H9B	106 (3)	H29A—C29—H29B	101 (2)
C9—C10—C11	110.1 (4)	C29—C30—C31	110.6 (4)
C9—C10—H10B	108.8 (16)	C29—C30—H30B	109.3 (18)
C11—C10—H10B	112.8 (16)	C31—C30—H30B	115.0 (17)
C9—C10—H10A	109.7 (18)	C29—C30—H30A	115 (2)
C11—C10—H10A	114.1 (19)	C31—C30—H30A	109 (2)
H10B—C10—H10A	101 (2)	H30B—C30—H30A	98 (3)
C12—C11—C10	114.3 (4)	C32—C31—C30	112.8 (4)
C12—C11—H11A	91 (3)	C32—C31—H31B	100 (2)
C10—C11—H11A	111 (2)	C30—C31—H31B	113 (2)
C12—C11—H11B	101 (2)	C32—C31—H31A	116 (2)
C10—C11—H11B	108 (2)	C30—C31—H31A	107 (2)
H11A—C11—H11B	129 (3)	H31B—C31—H31A	109 (3)
C11—C12—H12A	109.5	C31—C32—H32A	109.5
C11—C12—H12B	109.5	C31—C32—H32B	109.5
H12A—C12—H12B	109.5	H32A—C32—H32B	109.5
C11—C12—H12C	109.5	C31—C32—H32C	109.5
H12A—C12—H12C	109.5	H32A—C32—H32C	109.5
H12B—C12—H12C	109.5	H32B—C32—H32C	109.5
C8—N1—C1—O1	179.0 (3)	C28—N2—C21—O3	178.2 (4)
C9—N1—C1—O1	0.6 (5)	C29—N2—C21—O3	5.0 (6)
C8—N1—C1—C2	−1.6 (3)	C28—N2—C21—C22	−0.5 (4)
C9—N1—C1—C2	180.0 (3)	C29—N2—C21—C22	−173.6 (3)
O1—C1—C2—O2	0.6 (5)	O3—C21—C22—O4	1.8 (6)
N1—C1—C2—O2	−178.8 (3)	N2—C21—C22—O4	−179.6 (3)
O1—C1—C2—C3	−179.3 (3)	O3—C21—C22—C23	−178.2 (3)
N1—C1—C2—C3	1.3 (3)	N2—C21—C22—C23	0.4 (3)
O2—C2—C3—C4	0.2 (6)	O4—C22—C23—C24	−2.7 (7)
C1—C2—C3—C4	−180.0 (3)	C21—C22—C23—C24	177.3 (4)
O2—C2—C3—C8	179.6 (3)	O4—C22—C23—C28	179.8 (4)
C1—C2—C3—C8	−0.5 (3)	C21—C22—C23—C28	−0.2 (4)
C8—C3—C4—C5	0.7 (5)	C28—C23—C24—C25	−0.3 (5)
C2—C3—C4—C5	180.0 (3)	C22—C23—C24—C25	−177.6 (4)
C3—C4—C5—C6	−0.5 (5)	C23—C24—C25—C26	−0.8 (5)
C4—C5—C6—C7	−0.2 (5)	C24—C25—C26—C27	0.8 (6)
C4—C5—C6—Br1	−179.9 (2)	C24—C25—C26—Br2	−179.0 (3)
C5—C6—C7—C8	0.8 (5)	C25—C26—C27—C28	0.2 (5)
Br1—C6—C7—C8	−179.6 (2)	Br2—C26—C27—C28	−180.0 (2)
C6—C7—C8—C3	−0.6 (4)	C26—C27—C28—C23	−1.3 (5)
C6—C7—C8—N1	−179.6 (3)	C26—C27—C28—N2	177.9 (3)
C4—C3—C8—C7	−0.1 (5)	C24—C23—C28—C27	1.4 (5)
C2—C3—C8—C7	−179.6 (3)	C22—C23—C28—C27	179.3 (3)
C4—C3—C8—N1	179.1 (3)	C24—C23—C28—N2	−177.9 (3)
C2—C3—C8—N1	−0.4 (3)	C22—C23—C28—N2	0.0 (4)
C1—N1—C8—C7	−179.6 (3)	C21—N2—C28—C27	−179.0 (3)
C9—N1—C8—C7	−1.2 (5)	C29—N2—C28—C27	−5.9 (5)
C1—N1—C8—C3	1.3 (3)	C21—N2—C28—C23	0.3 (4)
C9—N1—C8—C3	179.7 (3)	C29—N2—C28—C23	173.4 (3)
C1—N1—C9—C10	89.8 (4)	C21—N2—C29—C30	−106.6 (4)
C8—N1—C9—C10	−88.3 (4)	C28—N2—C29—C30	81.2 (4)
N1—C9—C10—C11	179.3 (3)	N2—C29—C30—C31	−177.1 (3)
C9—C10—C11—C12	172.4 (4)	C29—C30—C31—C32	174.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3i	0.95 (3)	2.44 (3)	3.367 (5)	165 (2)

Table 1

Selected bond lengths (Å)

N1—C1	1.375 (3)
N1—C8	1.411 (4)
N1—C9	1.425 (4)
C1—C2	1.545 (4)
N2—C21	1.373 (3)
N2—C28	1.401 (3)
N2—C29	1.467 (4)
C21—C22	1.558 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O3i	0.95 (3)	2.44 (3)	3.367 (5)	165 (2)

Symmetry code: (i) .