The crystal structure of the title compound, C
15H
10BrNO
2, is stabilized by weak C—H
O hydrogen bonds. The dihedral angle between the phthalimide unit and the benzene ring is 71.7 (2)°.
Supporting information
CCDC reference: 640419
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.036
- wR factor = 0.101
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.02
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O2 .. 3.21 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 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
checkCIF publication errors
Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 109
The crystal structure of the title compound, C~15~H~10~Br~NO~2~, is stabilized
If you require a ~ then it should be escaped
with a \, i.e. \~
Otherwise there must be a matching closing ~, e.g. C~2~H~4~
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
5-bromo-2-
p-tolylisoindoline-1,3-dione
top
Crystal data top
C15H10BrNO2 | F(000) = 632 |
Mr = 316.15 | Dx = 1.636 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1912 reflections |
a = 8.1771 (15) Å | θ = 2.6–24.4° |
b = 15.5882 (3) Å | µ = 3.20 mm−1 |
c = 10.1816 (19) Å | T = 294 K |
β = 98.526 (3)° | Plate, colourless |
V = 1283.5 (4) Å3 | 0.22 × 0.18 × 0.16 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2622 independent reflections |
Radiation source: fine-focus sealed tube | 1574 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ and ω scans | θmax = 26.4°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −10→9 |
Tmin = 0.540, Tmax = 0.629 | k = −9→19 |
7233 measured reflections | l = −12→12 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0462P)2 + 0.4709P] where P = (Fo2 + 2Fc2)/3 |
2622 reflections | (Δ/σ)max = 0.001 |
173 parameters | Δρmax = 0.59 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
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 | Uiso*/Ueq | |
Br1 | 0.24876 (6) | 0.46996 (3) | −0.21925 (4) | 0.05888 (19) | |
O1 | 0.1439 (3) | 0.69493 (17) | 0.2213 (2) | 0.0475 (7) | |
O2 | 0.3081 (3) | 0.45985 (16) | 0.4765 (2) | 0.0478 (7) | |
N1 | 0.2215 (3) | 0.58947 (19) | 0.3787 (2) | 0.0330 (7) | |
C1 | 0.1899 (4) | 0.6231 (2) | 0.2499 (3) | 0.0336 (8) | |
C2 | 0.2263 (4) | 0.5522 (2) | 0.1607 (3) | 0.0338 (8) | |
C3 | 0.2162 (4) | 0.5509 (2) | 0.0238 (3) | 0.0409 (9) | |
H3 | 0.1836 | 0.5989 | −0.0277 | 0.049* | |
C4 | 0.2567 (4) | 0.4748 (2) | −0.0325 (3) | 0.0391 (9) | |
C5 | 0.3022 (4) | 0.4020 (2) | 0.0425 (3) | 0.0429 (9) | |
H5 | 0.3261 | 0.3514 | 0.0008 | 0.051* | |
C6 | 0.3121 (4) | 0.4046 (2) | 0.1798 (3) | 0.0408 (9) | |
H6 | 0.3433 | 0.3565 | 0.2315 | 0.049* | |
C7 | 0.2740 (4) | 0.4810 (2) | 0.2370 (3) | 0.0324 (8) | |
C8 | 0.2740 (4) | 0.5031 (2) | 0.3792 (4) | 0.0345 (8) | |
C9 | 0.1892 (4) | 0.6357 (2) | 0.4950 (3) | 0.0326 (8) | |
C10 | 0.3167 (4) | 0.6626 (2) | 0.5884 (3) | 0.0370 (9) | |
H10 | 0.4258 | 0.6527 | 0.5768 | 0.044* | |
C11 | 0.2807 (4) | 0.7050 (2) | 0.7007 (3) | 0.0395 (9) | |
H11 | 0.3673 | 0.7231 | 0.7644 | 0.047* | |
C12 | 0.1202 (4) | 0.7210 (2) | 0.7204 (3) | 0.0349 (8) | |
C13 | −0.0057 (5) | 0.6939 (3) | 0.6225 (3) | 0.0475 (10) | |
H13 | −0.1151 | 0.7045 | 0.6327 | 0.057* | |
C14 | 0.0278 (4) | 0.6518 (3) | 0.5110 (3) | 0.0450 (10) | |
H14 | −0.0583 | 0.6343 | 0.4464 | 0.054* | |
C15 | 0.0812 (5) | 0.7656 (3) | 0.8443 (3) | 0.0468 (10) | |
H15A | 0.1782 | 0.7663 | 0.9101 | 0.070* | |
H15B | −0.0057 | 0.7353 | 0.8783 | 0.070* | |
H15C | 0.0464 | 0.8234 | 0.8229 | 0.070* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0917 (4) | 0.0573 (3) | 0.0292 (2) | −0.0060 (3) | 0.01385 (19) | −0.0085 (2) |
O1 | 0.0672 (18) | 0.0338 (16) | 0.0429 (15) | 0.0089 (14) | 0.0129 (13) | −0.0010 (12) |
O2 | 0.0696 (18) | 0.0440 (16) | 0.0296 (13) | 0.0046 (14) | 0.0063 (12) | 0.0086 (12) |
N1 | 0.0417 (17) | 0.0322 (17) | 0.0253 (13) | 0.0005 (14) | 0.0058 (12) | −0.0020 (13) |
C1 | 0.038 (2) | 0.033 (2) | 0.0309 (17) | 0.0003 (17) | 0.0069 (15) | −0.0009 (16) |
C2 | 0.040 (2) | 0.030 (2) | 0.0309 (17) | −0.0002 (16) | 0.0037 (15) | −0.0012 (16) |
C3 | 0.055 (2) | 0.038 (2) | 0.0293 (18) | 0.0000 (18) | 0.0057 (17) | 0.0016 (16) |
C4 | 0.052 (2) | 0.044 (2) | 0.0223 (16) | −0.005 (2) | 0.0081 (16) | −0.0079 (17) |
C5 | 0.058 (2) | 0.033 (2) | 0.0388 (19) | 0.0017 (19) | 0.0101 (18) | −0.0074 (18) |
C6 | 0.055 (2) | 0.032 (2) | 0.0354 (18) | 0.0053 (19) | 0.0063 (17) | −0.0014 (17) |
C7 | 0.036 (2) | 0.033 (2) | 0.0287 (17) | −0.0018 (17) | 0.0052 (15) | −0.0019 (15) |
C8 | 0.038 (2) | 0.034 (2) | 0.0321 (19) | −0.0036 (17) | 0.0059 (16) | −0.0036 (16) |
C9 | 0.040 (2) | 0.034 (2) | 0.0258 (16) | −0.0019 (16) | 0.0108 (15) | −0.0050 (15) |
C10 | 0.0327 (19) | 0.046 (2) | 0.0322 (18) | −0.0004 (18) | 0.0053 (16) | −0.0042 (17) |
C11 | 0.038 (2) | 0.047 (2) | 0.0320 (18) | −0.0047 (18) | 0.0008 (16) | −0.0084 (17) |
C12 | 0.041 (2) | 0.034 (2) | 0.0300 (18) | 0.0002 (17) | 0.0083 (17) | −0.0006 (15) |
C13 | 0.033 (2) | 0.070 (3) | 0.040 (2) | −0.002 (2) | 0.0075 (17) | −0.014 (2) |
C14 | 0.037 (2) | 0.062 (3) | 0.036 (2) | −0.007 (2) | 0.0048 (17) | −0.0156 (19) |
C15 | 0.055 (2) | 0.049 (3) | 0.038 (2) | 0.004 (2) | 0.0114 (18) | −0.0101 (19) |
Geometric parameters (Å, º) top
Br1—C4 | 1.894 (3) | C7—C8 | 1.488 (5) |
O1—C1 | 1.203 (4) | C9—C10 | 1.369 (5) |
O2—C8 | 1.196 (4) | C9—C14 | 1.376 (5) |
N1—C1 | 1.400 (4) | C10—C11 | 1.390 (5) |
N1—C8 | 1.413 (5) | C10—H10 | 0.9300 |
N1—C9 | 1.443 (4) | C11—C12 | 1.380 (5) |
C1—C2 | 1.489 (5) | C11—H11 | 0.9300 |
C2—C7 | 1.377 (5) | C12—C13 | 1.388 (5) |
C2—C3 | 1.384 (5) | C12—C15 | 1.515 (5) |
C3—C4 | 1.379 (5) | C13—C14 | 1.374 (5) |
C3—H3 | 0.9300 | C13—H13 | 0.9300 |
C4—C5 | 1.387 (5) | C14—H14 | 0.9300 |
C5—C6 | 1.389 (5) | C15—H15A | 0.9600 |
C5—H5 | 0.9300 | C15—H15B | 0.9600 |
C6—C7 | 1.381 (5) | C15—H15C | 0.9600 |
C6—H6 | 0.9300 | | |
| | | |
C1—N1—C8 | 111.9 (3) | N1—C8—C7 | 105.1 (3) |
C1—N1—C9 | 123.4 (3) | C10—C9—C14 | 120.5 (3) |
C8—N1—C9 | 124.4 (3) | C10—C9—N1 | 120.6 (3) |
O1—C1—N1 | 125.7 (3) | C14—C9—N1 | 118.9 (3) |
O1—C1—C2 | 128.8 (3) | C9—C10—C11 | 119.0 (3) |
N1—C1—C2 | 105.6 (3) | C9—C10—H10 | 120.5 |
C7—C2—C3 | 121.7 (3) | C11—C10—H10 | 120.5 |
C7—C2—C1 | 108.6 (3) | C12—C11—C10 | 121.8 (3) |
C3—C2—C1 | 129.6 (3) | C12—C11—H11 | 119.1 |
C4—C3—C2 | 116.7 (3) | C10—C11—H11 | 119.1 |
C4—C3—H3 | 121.7 | C11—C12—C13 | 117.5 (3) |
C2—C3—H3 | 121.7 | C11—C12—C15 | 121.7 (3) |
C3—C4—C5 | 122.4 (3) | C13—C12—C15 | 120.8 (3) |
C3—C4—Br1 | 118.5 (3) | C14—C13—C12 | 121.4 (3) |
C5—C4—Br1 | 119.1 (3) | C14—C13—H13 | 119.3 |
C4—C5—C6 | 120.1 (3) | C12—C13—H13 | 119.3 |
C4—C5—H5 | 120.0 | C13—C14—C9 | 119.8 (3) |
C6—C5—H5 | 120.0 | C13—C14—H14 | 120.1 |
C7—C6—C5 | 117.8 (3) | C9—C14—H14 | 120.1 |
C7—C6—H6 | 121.1 | C12—C15—H15A | 109.5 |
C5—C6—H6 | 121.1 | C12—C15—H15B | 109.5 |
C2—C7—C6 | 121.3 (3) | H15A—C15—H15B | 109.5 |
C2—C7—C8 | 108.8 (3) | C12—C15—H15C | 109.5 |
C6—C7—C8 | 129.9 (3) | H15A—C15—H15C | 109.5 |
O2—C8—N1 | 124.9 (3) | H15B—C15—H15C | 109.5 |
O2—C8—C7 | 129.9 (3) | | |
| | | |
C8—N1—C1—O1 | −179.9 (4) | C9—N1—C8—O2 | −5.1 (6) |
C9—N1—C1—O1 | 5.4 (5) | C1—N1—C8—C7 | −0.3 (4) |
C8—N1—C1—C2 | −0.4 (4) | C9—N1—C8—C7 | 174.3 (3) |
C9—N1—C1—C2 | −175.1 (3) | C2—C7—C8—O2 | −179.7 (4) |
O1—C1—C2—C7 | −179.5 (4) | C6—C7—C8—O2 | 0.6 (7) |
N1—C1—C2—C7 | 1.0 (4) | C2—C7—C8—N1 | 0.9 (4) |
O1—C1—C2—C3 | −0.3 (7) | C6—C7—C8—N1 | −178.8 (3) |
N1—C1—C2—C3 | −179.8 (3) | C1—N1—C9—C10 | −112.1 (4) |
C7—C2—C3—C4 | −0.2 (5) | C8—N1—C9—C10 | 73.8 (5) |
C1—C2—C3—C4 | −179.4 (3) | C1—N1—C9—C14 | 68.2 (4) |
C2—C3—C4—C5 | 1.4 (6) | C8—N1—C9—C14 | −105.8 (4) |
C2—C3—C4—Br1 | −178.9 (3) | C14—C9—C10—C11 | 1.3 (5) |
C3—C4—C5—C6 | −1.6 (6) | N1—C9—C10—C11 | −178.4 (3) |
Br1—C4—C5—C6 | 178.7 (3) | C9—C10—C11—C12 | −0.3 (6) |
C4—C5—C6—C7 | 0.6 (5) | C10—C11—C12—C13 | −0.7 (6) |
C3—C2—C7—C6 | −0.7 (5) | C10—C11—C12—C15 | 178.7 (3) |
C1—C2—C7—C6 | 178.6 (3) | C11—C12—C13—C14 | 0.7 (6) |
C3—C2—C7—C8 | 179.5 (3) | C15—C12—C13—C14 | −178.6 (4) |
C1—C2—C7—C8 | −1.2 (4) | C12—C13—C14—C9 | 0.2 (6) |
C5—C6—C7—C2 | 0.5 (5) | C10—C9—C14—C13 | −1.2 (6) |
C5—C6—C7—C8 | −179.8 (3) | N1—C9—C14—C13 | 178.4 (4) |
C1—N1—C8—O2 | −179.7 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1i | 0.93 | 2.56 | 3.423 (4) | 154 |
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2. |