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The crystal structure of the title compound, C15H10BrNO2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807008975/lh2315sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807008975/lh2315Isup2.hkl
Contains datablock I

CCDC reference: 640419

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](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

Computing details top

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
C15H10BrNO2F(000) = 632
Mr = 316.15Dx = 1.636 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1912 reflections
a = 8.1771 (15) Åθ = 2.6–24.4°
b = 15.5882 (3) ŵ = 3.20 mm1
c = 10.1816 (19) ÅT = 294 K
β = 98.526 (3)°Plate, colourless
V = 1283.5 (4) Å30.22 × 0.18 × 0.16 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2622 independent reflections
Radiation source: fine-focus sealed tube1574 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 26.4°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 109
Tmin = 0.540, Tmax = 0.629k = 919
7233 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-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 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = 0.29 e Å3
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
xyzUiso*/Ueq
Br10.24876 (6)0.46996 (3)0.21925 (4)0.05888 (19)
O10.1439 (3)0.69493 (17)0.2213 (2)0.0475 (7)
O20.3081 (3)0.45985 (16)0.4765 (2)0.0478 (7)
N10.2215 (3)0.58947 (19)0.3787 (2)0.0330 (7)
C10.1899 (4)0.6231 (2)0.2499 (3)0.0336 (8)
C20.2263 (4)0.5522 (2)0.1607 (3)0.0338 (8)
C30.2162 (4)0.5509 (2)0.0238 (3)0.0409 (9)
H30.18360.59890.02770.049*
C40.2567 (4)0.4748 (2)0.0325 (3)0.0391 (9)
C50.3022 (4)0.4020 (2)0.0425 (3)0.0429 (9)
H50.32610.35140.00080.051*
C60.3121 (4)0.4046 (2)0.1798 (3)0.0408 (9)
H60.34330.35650.23150.049*
C70.2740 (4)0.4810 (2)0.2370 (3)0.0324 (8)
C80.2740 (4)0.5031 (2)0.3792 (4)0.0345 (8)
C90.1892 (4)0.6357 (2)0.4950 (3)0.0326 (8)
C100.3167 (4)0.6626 (2)0.5884 (3)0.0370 (9)
H100.42580.65270.57680.044*
C110.2807 (4)0.7050 (2)0.7007 (3)0.0395 (9)
H110.36730.72310.76440.047*
C120.1202 (4)0.7210 (2)0.7204 (3)0.0349 (8)
C130.0057 (5)0.6939 (3)0.6225 (3)0.0475 (10)
H130.11510.70450.63270.057*
C140.0278 (4)0.6518 (3)0.5110 (3)0.0450 (10)
H140.05830.63430.44640.054*
C150.0812 (5)0.7656 (3)0.8443 (3)0.0468 (10)
H15A0.17820.76630.91010.070*
H15B0.00570.73530.87830.070*
H15C0.04640.82340.82290.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0917 (4)0.0573 (3)0.0292 (2)0.0060 (3)0.01385 (19)0.0085 (2)
O10.0672 (18)0.0338 (16)0.0429 (15)0.0089 (14)0.0129 (13)0.0010 (12)
O20.0696 (18)0.0440 (16)0.0296 (13)0.0046 (14)0.0063 (12)0.0086 (12)
N10.0417 (17)0.0322 (17)0.0253 (13)0.0005 (14)0.0058 (12)0.0020 (13)
C10.038 (2)0.033 (2)0.0309 (17)0.0003 (17)0.0069 (15)0.0009 (16)
C20.040 (2)0.030 (2)0.0309 (17)0.0002 (16)0.0037 (15)0.0012 (16)
C30.055 (2)0.038 (2)0.0293 (18)0.0000 (18)0.0057 (17)0.0016 (16)
C40.052 (2)0.044 (2)0.0223 (16)0.005 (2)0.0081 (16)0.0079 (17)
C50.058 (2)0.033 (2)0.0388 (19)0.0017 (19)0.0101 (18)0.0074 (18)
C60.055 (2)0.032 (2)0.0354 (18)0.0053 (19)0.0063 (17)0.0014 (17)
C70.036 (2)0.033 (2)0.0287 (17)0.0018 (17)0.0052 (15)0.0019 (15)
C80.038 (2)0.034 (2)0.0321 (19)0.0036 (17)0.0059 (16)0.0036 (16)
C90.040 (2)0.034 (2)0.0258 (16)0.0019 (16)0.0108 (15)0.0050 (15)
C100.0327 (19)0.046 (2)0.0322 (18)0.0004 (18)0.0053 (16)0.0042 (17)
C110.038 (2)0.047 (2)0.0320 (18)0.0047 (18)0.0008 (16)0.0084 (17)
C120.041 (2)0.034 (2)0.0300 (18)0.0002 (17)0.0083 (17)0.0006 (15)
C130.033 (2)0.070 (3)0.040 (2)0.002 (2)0.0075 (17)0.014 (2)
C140.037 (2)0.062 (3)0.036 (2)0.007 (2)0.0048 (17)0.0156 (19)
C150.055 (2)0.049 (3)0.038 (2)0.004 (2)0.0114 (18)0.0101 (19)
Geometric parameters (Å, º) top
Br1—C41.894 (3)C7—C81.488 (5)
O1—C11.203 (4)C9—C101.369 (5)
O2—C81.196 (4)C9—C141.376 (5)
N1—C11.400 (4)C10—C111.390 (5)
N1—C81.413 (5)C10—H100.9300
N1—C91.443 (4)C11—C121.380 (5)
C1—C21.489 (5)C11—H110.9300
C2—C71.377 (5)C12—C131.388 (5)
C2—C31.384 (5)C12—C151.515 (5)
C3—C41.379 (5)C13—C141.374 (5)
C3—H30.9300C13—H130.9300
C4—C51.387 (5)C14—H140.9300
C5—C61.389 (5)C15—H15A0.9600
C5—H50.9300C15—H15B0.9600
C6—C71.381 (5)C15—H15C0.9600
C6—H60.9300
C1—N1—C8111.9 (3)N1—C8—C7105.1 (3)
C1—N1—C9123.4 (3)C10—C9—C14120.5 (3)
C8—N1—C9124.4 (3)C10—C9—N1120.6 (3)
O1—C1—N1125.7 (3)C14—C9—N1118.9 (3)
O1—C1—C2128.8 (3)C9—C10—C11119.0 (3)
N1—C1—C2105.6 (3)C9—C10—H10120.5
C7—C2—C3121.7 (3)C11—C10—H10120.5
C7—C2—C1108.6 (3)C12—C11—C10121.8 (3)
C3—C2—C1129.6 (3)C12—C11—H11119.1
C4—C3—C2116.7 (3)C10—C11—H11119.1
C4—C3—H3121.7C11—C12—C13117.5 (3)
C2—C3—H3121.7C11—C12—C15121.7 (3)
C3—C4—C5122.4 (3)C13—C12—C15120.8 (3)
C3—C4—Br1118.5 (3)C14—C13—C12121.4 (3)
C5—C4—Br1119.1 (3)C14—C13—H13119.3
C4—C5—C6120.1 (3)C12—C13—H13119.3
C4—C5—H5120.0C13—C14—C9119.8 (3)
C6—C5—H5120.0C13—C14—H14120.1
C7—C6—C5117.8 (3)C9—C14—H14120.1
C7—C6—H6121.1C12—C15—H15A109.5
C5—C6—H6121.1C12—C15—H15B109.5
C2—C7—C6121.3 (3)H15A—C15—H15B109.5
C2—C7—C8108.8 (3)C12—C15—H15C109.5
C6—C7—C8129.9 (3)H15A—C15—H15C109.5
O2—C8—N1124.9 (3)H15B—C15—H15C109.5
O2—C8—C7129.9 (3)
C8—N1—C1—O1179.9 (4)C9—N1—C8—O25.1 (6)
C9—N1—C1—O15.4 (5)C1—N1—C8—C70.3 (4)
C8—N1—C1—C20.4 (4)C9—N1—C8—C7174.3 (3)
C9—N1—C1—C2175.1 (3)C2—C7—C8—O2179.7 (4)
O1—C1—C2—C7179.5 (4)C6—C7—C8—O20.6 (7)
N1—C1—C2—C71.0 (4)C2—C7—C8—N10.9 (4)
O1—C1—C2—C30.3 (7)C6—C7—C8—N1178.8 (3)
N1—C1—C2—C3179.8 (3)C1—N1—C9—C10112.1 (4)
C7—C2—C3—C40.2 (5)C8—N1—C9—C1073.8 (5)
C1—C2—C3—C4179.4 (3)C1—N1—C9—C1468.2 (4)
C2—C3—C4—C51.4 (6)C8—N1—C9—C14105.8 (4)
C2—C3—C4—Br1178.9 (3)C14—C9—C10—C111.3 (5)
C3—C4—C5—C61.6 (6)N1—C9—C10—C11178.4 (3)
Br1—C4—C5—C6178.7 (3)C9—C10—C11—C120.3 (6)
C4—C5—C6—C70.6 (5)C10—C11—C12—C130.7 (6)
C3—C2—C7—C60.7 (5)C10—C11—C12—C15178.7 (3)
C1—C2—C7—C6178.6 (3)C11—C12—C13—C140.7 (6)
C3—C2—C7—C8179.5 (3)C15—C12—C13—C14178.6 (4)
C1—C2—C7—C81.2 (4)C12—C13—C14—C90.2 (6)
C5—C6—C7—C20.5 (5)C10—C9—C14—C131.2 (6)
C5—C6—C7—C8179.8 (3)N1—C9—C14—C13178.4 (4)
C1—N1—C8—O2179.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.932.563.423 (4)154
Symmetry code: (i) x+1/2, y1/2, z+1/2.
 

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