The title compound, C
8H
4BrNO
2, has a single planar molecule in the asymmetric unit with the non-H atoms possessing a mean deviation from planarity of 0.024 Å. The molecules dimerize in the solid state through N—H

O hydrogen bonds. There are intermolecular Br

O close contacts at 3.0430 (14) Å. The nine-membered rings of the isatins stack along [001] with parallel slipped π–π interactions [inter-centroid distance: 3.7173 (6) Å, inter-planar distance: 3.3110 (8) Å, slippage: 1.6898 (14) Å].
Supporting information
CCDC reference: 1445034
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.019
- wR factor = 0.049
- Data-to-parameter ratio = 12.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT369_ALERT_2_B Long C(sp2)-C(sp2) Bond C1 - C2 .. 1.57 Ang.
PLAT431_ALERT_2_B Short Inter HL..A Contact Br1 .. O2 .. 3.04 Ang.
Alert level C
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 1 Note
Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 2 Note
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 1 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 1 Report
0 ALERT level A = Most likely a serious problem - resolve or explain
2 ALERT level B = A potentially serious problem, consider carefully
1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
4 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 and publCIF (Westrip, 2010).
4-Bromo-1
H-indole-2,3-dione
top
Crystal data top
C8H4BrNO2 | F(000) = 440 |
Mr = 226.03 | Dx = 2.047 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8354 reflections |
a = 7.3655 (11) Å | θ = 3.0–25.6° |
b = 13.689 (2) Å | µ = 5.55 mm−1 |
c = 7.2866 (12) Å | T = 120 K |
β = 93.378 (5)° | BLOCK, orange |
V = 733.4 (2) Å3 | 0.2 × 0.2 × 0.1 mm |
Z = 4 | |
Data collection top
Bruker D8 Venture CMOS diffractometer | 1381 independent reflections |
Radiation source: Mo | 1285 reflections with I > 2σ(I) |
TRIUMPH monochromator | Rint = 0.034 |
φ and ω scans | θmax = 25.6°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −8→8 |
Tmin = 0.174, Tmax = 0.259 | k = −16→16 |
12353 measured reflections | l = −8→8 |
Refinement top
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.019 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.049 | w = 1/[σ2(Fo2) + (0.0276P)2 + 0.4818P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
1381 reflections | Δρmax = 0.46 e Å−3 |
112 parameters | Δρmin = −0.45 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 0.77232 (2) | 0.02480 (2) | 0.59115 (3) | 0.01707 (9) | |
O1 | 1.14710 (19) | 0.39227 (10) | 0.4387 (2) | 0.0203 (3) | |
O2 | 1.08320 (19) | 0.18127 (10) | 0.4576 (2) | 0.0193 (3) | |
N1 | 0.8665 (2) | 0.39792 (12) | 0.5663 (2) | 0.0154 (3) | |
H1 | 0.834 (3) | 0.4616 (12) | 0.575 (3) | 0.018* | |
C1 | 1.0132 (3) | 0.35425 (13) | 0.4988 (2) | 0.0152 (4) | |
C2 | 0.9784 (3) | 0.24155 (13) | 0.5103 (2) | 0.0132 (4) | |
C3 | 0.8006 (2) | 0.23315 (14) | 0.5902 (2) | 0.0121 (4) | |
C4 | 0.6908 (3) | 0.15392 (14) | 0.6301 (2) | 0.0140 (4) | |
C5 | 0.5213 (3) | 0.17041 (15) | 0.6988 (3) | 0.0167 (4) | |
H5 | 0.4463 | 0.1169 | 0.7285 | 0.020* | |
C6 | 0.4620 (3) | 0.26585 (15) | 0.7239 (2) | 0.0170 (4) | |
H6 | 0.3457 | 0.2762 | 0.7704 | 0.020* | |
C7 | 0.5677 (3) | 0.34683 (15) | 0.6832 (3) | 0.0160 (4) | |
H7 | 0.5253 | 0.4116 | 0.6999 | 0.019* | |
C8 | 0.7367 (3) | 0.32875 (14) | 0.6174 (2) | 0.0126 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.01757 (13) | 0.01081 (13) | 0.02316 (13) | −0.00138 (7) | 0.00398 (8) | 0.00006 (7) |
O1 | 0.0166 (7) | 0.0146 (7) | 0.0303 (8) | −0.0016 (6) | 0.0073 (6) | 0.0022 (6) |
O2 | 0.0169 (7) | 0.0139 (7) | 0.0278 (8) | 0.0028 (6) | 0.0075 (6) | −0.0008 (6) |
N1 | 0.0152 (8) | 0.0096 (8) | 0.0217 (8) | 0.0017 (6) | 0.0039 (6) | −0.0004 (7) |
C1 | 0.0167 (10) | 0.0128 (9) | 0.0160 (9) | 0.0004 (8) | 0.0009 (7) | 0.0006 (8) |
C2 | 0.0136 (9) | 0.0123 (9) | 0.0138 (8) | 0.0009 (7) | 0.0000 (7) | 0.0000 (7) |
C3 | 0.0123 (9) | 0.0124 (9) | 0.0114 (8) | 0.0010 (7) | 0.0000 (7) | −0.0007 (7) |
C4 | 0.0160 (9) | 0.0128 (9) | 0.0129 (8) | 0.0001 (7) | −0.0001 (7) | −0.0004 (7) |
C5 | 0.0148 (9) | 0.0194 (10) | 0.0160 (9) | −0.0026 (8) | 0.0023 (7) | 0.0008 (8) |
C6 | 0.0121 (9) | 0.0259 (11) | 0.0134 (8) | 0.0016 (8) | 0.0026 (7) | −0.0017 (8) |
C7 | 0.0165 (10) | 0.0171 (10) | 0.0144 (9) | 0.0046 (8) | 0.0003 (7) | −0.0016 (7) |
C8 | 0.0146 (9) | 0.0114 (9) | 0.0116 (8) | −0.0004 (7) | 0.0002 (7) | −0.0007 (7) |
Geometric parameters (Å, º) top
Br1—C4 | 1.8933 (19) | C3—C8 | 1.409 (3) |
O1—C1 | 1.219 (2) | C4—C5 | 1.391 (3) |
O2—C2 | 1.208 (2) | C5—H5 | 0.9500 |
N1—H1 | 0.908 (16) | C5—C6 | 1.393 (3) |
N1—C1 | 1.352 (3) | C6—H6 | 0.9500 |
N1—C8 | 1.411 (3) | C6—C7 | 1.396 (3) |
C1—C2 | 1.567 (3) | C7—H7 | 0.9500 |
C2—C3 | 1.468 (3) | C7—C8 | 1.382 (3) |
C3—C4 | 1.394 (3) | | |
| | | |
C1—N1—H1 | 132.2 (17) | C5—C4—C3 | 119.55 (18) |
C1—N1—C8 | 111.58 (16) | C4—C5—H5 | 120.2 |
C8—N1—H1 | 116.0 (17) | C4—C5—C6 | 119.62 (18) |
O1—C1—N1 | 128.50 (17) | C6—C5—H5 | 120.2 |
O1—C1—C2 | 125.29 (17) | C5—C6—H6 | 118.9 |
N1—C1—C2 | 106.20 (15) | C5—C6—C7 | 122.26 (18) |
O2—C2—C1 | 123.09 (17) | C7—C6—H6 | 118.9 |
O2—C2—C3 | 132.38 (18) | C6—C7—H7 | 121.4 |
C3—C2—C1 | 104.52 (15) | C8—C7—C6 | 117.14 (18) |
C4—C3—C2 | 133.28 (18) | C8—C7—H7 | 121.4 |
C4—C3—C8 | 119.37 (17) | C3—C8—N1 | 110.39 (16) |
C8—C3—C2 | 107.25 (16) | C7—C8—N1 | 127.55 (18) |
C3—C4—Br1 | 120.15 (14) | C7—C8—C3 | 122.05 (18) |
C5—C4—Br1 | 120.30 (15) | | |
| | | |
Br1—C4—C5—C6 | −178.98 (14) | C2—C3—C8—N1 | −2.3 (2) |
O1—C1—C2—O2 | −0.8 (3) | C2—C3—C8—C7 | 176.91 (16) |
O1—C1—C2—C3 | −179.57 (18) | C3—C4—C5—C6 | 1.1 (3) |
O2—C2—C3—C4 | −1.0 (4) | C4—C3—C8—N1 | −179.08 (16) |
O2—C2—C3—C8 | −177.2 (2) | C4—C3—C8—C7 | 0.1 (3) |
N1—C1—C2—O2 | 178.72 (18) | C4—C5—C6—C7 | −0.3 (3) |
N1—C1—C2—C3 | −0.04 (19) | C5—C6—C7—C8 | −0.5 (3) |
C1—N1—C8—C3 | 2.4 (2) | C6—C7—C8—N1 | 179.71 (17) |
C1—N1—C8—C7 | −176.77 (18) | C6—C7—C8—C3 | 0.6 (3) |
C1—C2—C3—C4 | 177.55 (18) | C8—N1—C1—O1 | 178.14 (19) |
C1—C2—C3—C8 | 1.40 (18) | C8—N1—C1—C2 | −1.4 (2) |
C2—C3—C4—Br1 | 3.3 (3) | C8—C3—C4—Br1 | 179.07 (13) |
C2—C3—C4—C5 | −176.79 (18) | C8—C3—C4—C5 | −1.0 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.91 (2) | 2.01 (2) | 2.874 (2) | 159 (2) |
Symmetry code: (i) −x+2, −y+1, −z+1. |