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The title compound, C14H8BrNO2, was obtained as an N-protected starting material for the syntheses of multidentate ligands bearing N-donor atoms. Its crystal structure is reported here. The structure contains two orthogonal planar moieties (the bromo­phenyl ring and the phthal­imide plane), with an interplanar angle of 79.2 (4)°. A short intermolecular Br...O distance of 3.070 (4) Å is observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802020263/ww6049sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802020263/ww6049Isup2.hkl
Contains datablock I

CCDC reference: 202330

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.068
  • wR factor = 0.054
  • Data-to-parameter ratio = 11.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

The crystal structure of N-(2-bromophenyl)phthalimide, (I), contains two almost perpendicular planar moieties with an interplanar angle of 79.2°. The bromophenyl and phthalimide rings are essentially individually planar, within 0.008 Å. All intramolecular distances are comparable to other aryl–phthalimide structures (Ribar et al., 1976; Voliotis et al., 1984). The short Br···O distance of 3.07 Å is shorter than the sum of van der Waals radii (1.85 + 1.52 Å), but longer than some of the reported Br···O contact distances (Doi et al., 1985). This short Br···O contact indicates a possible charge-transfer interaction or dipole–dipole interaction between the Br atom and the carbonyl O atom. The somewhat lower C—C bond precision is probably due to the nature of higher content of weak data [only 46.5% greater than 3σ(I)].

Experimental top

The titled compound, N-(2-bromophenyl)phthalimide, was obtained by adding phthalic anhydride (17.60 g) to liquid 2-bromoaniline (20.43 g) in a 1:1 molar ratio. The reaction mixture was heated with stiring until all the solid had dissolved (or reacted) and the temperature was maintained for a further ca 8 h. Cooling to room temperature led to a solidified product. Colorless crystals were obtained from a mixed solvent system of n-hexane and dichloromethane. The structure was supported by EI–MS (M+ = 302). The C, H, N and O contents were analyzed using a Heraeus CHN-O instrument. Analysis calculated for C14H8BrNO2: C 55.66, H 2.67, N 4.64, O 10.59%; found: C 55.26, H 2.70, N 4.68, O 10.55%.

Refinement top

Phenyl H atoms were placed on calculated positions with a C—H distance of 0.95 Å. All H atoms were included in the final cycles of least-squares refinement with fixed positional parameters and isotropic displacement parameters (1.2Ueq of the attached non-H atoms).

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1992-1997); program(s) used to solve structure: SIR92 (Altmare et al., 1993); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

Figures top
[Figure 1] Fig. 1. A view of the molecule of the title compound with 30% probability ellipsoids.
(I) top
Crystal data top
C14H8BrNO2F(000) = 600.00
Mr = 302.11Dx = 1.614 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ynCell parameters from 19 reflections
a = 11.330 (1) Åθ = 5.4–7.8°
b = 8.100 (1) ŵ = 3.30 mm1
c = 13.965 (1) ÅT = 298 K
β = 104.096 (9)°Prism, colorless
V = 1243.0 (2) Å30.60 × 0.56 × 0.48 mm
Z = 4
Data collection top
Rigaku AFC-7S
diffractometer
1882 reflections with I > σ(I)
Radiation source: X-ray tubeRint = 0.059
Graphite monochromatorθmax = 27.5°, θmin = 2.1°
ω–2θ scansh = 014
Absorption correction: empirical (using intensity measurements)
(North et al., 1968)
k = 010
Tmin = 0.155, Tmax = 0.200l = 1817
3208 measured reflections3 standard reflections every 150 reflections
2852 independent reflections intensity decay: 0.2%
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.068H-atom parameters constrained
wR(F2) = 0.054Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.00022|Fo|2]
S = 1.58(Δ/σ)max = 0.007
1882 reflectionsΔρmax = 0.78 e Å3
163 parametersΔρmin = 0.73 e Å3
Crystal data top
C14H8BrNO2V = 1243.0 (2) Å3
Mr = 302.11Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.330 (1) ŵ = 3.30 mm1
b = 8.100 (1) ÅT = 298 K
c = 13.965 (1) Å0.60 × 0.56 × 0.48 mm
β = 104.096 (9)°
Data collection top
Rigaku AFC-7S
diffractometer
1882 reflections with I > σ(I)
Absorption correction: empirical (using intensity measurements)
(North et al., 1968)
Rint = 0.059
Tmin = 0.155, Tmax = 0.2003 standard reflections every 150 reflections
3208 measured reflections intensity decay: 0.2%
2852 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.054H-atom parameters constrained
S = 1.58Δρmax = 0.78 e Å3
1882 reflectionsΔρmin = 0.73 e Å3
163 parameters
Special details top

Experimental. The scan width was (1.57 + 0.35tanθ)° with an ω scan speed of 0° per minute (up to 5 scans to achieve I/σ(I) > 15). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.65623 (5)0.17246 (8)0.65972 (4)0.0733 (2)
O10.9013 (3)0.2749 (4)0.5373 (2)0.057 (1)
O20.9976 (3)0.0217 (5)0.8238 (3)0.077 (1)
N10.9286 (3)0.0949 (4)0.6697 (3)0.042 (1)
C10.8461 (4)0.0330 (5)0.6245 (3)0.042 (1)
C20.7222 (4)0.0175 (6)0.6145 (3)0.045 (1)
C30.6458 (4)0.1427 (7)0.5696 (4)0.061 (2)
C40.6928 (6)0.2821 (7)0.5362 (4)0.067 (2)
C50.8143 (6)0.2970 (6)0.5465 (4)0.068 (2)
C60.8923 (4)0.1736 (6)0.5902 (4)0.055 (2)
C71.0394 (3)0.3350 (5)0.6953 (3)0.039 (1)
C81.0691 (4)0.2454 (6)0.7826 (3)0.041 (1)
C91.1545 (4)0.3001 (6)0.8642 (3)0.053 (1)
C101.2065 (4)0.4526 (7)0.8568 (4)0.060 (2)
C111.1761 (4)0.5444 (6)0.7709 (4)0.059 (2)
C121.0931 (4)0.4855 (6)0.6880 (4)0.055 (2)
C130.9490 (4)0.2412 (6)0.6221 (3)0.043 (1)
C140.9992 (4)0.0900 (6)0.7678 (3)0.050 (1)
H10.56040.13280.56180.073*
H20.63980.36810.50590.081*
H30.84590.39360.52320.081*
H40.97740.18460.59680.067*
H51.17650.23620.92290.063*
H61.26470.49520.91200.072*
H71.21240.64960.76870.071*
H81.07410.54680.62820.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0642 (4)0.0854 (5)0.0730 (4)0.0066 (3)0.0218 (3)0.0266 (4)
O10.064 (2)0.061 (2)0.034 (2)0.008 (2)0.009 (2)0.009 (2)
O20.092 (3)0.073 (3)0.051 (2)0.027 (2)0.014 (2)0.025 (2)
N10.046 (2)0.043 (2)0.032 (2)0.005 (2)0.001 (2)0.005 (2)
C10.047 (2)0.041 (3)0.033 (2)0.005 (2)0.002 (2)0.004 (2)
C20.052 (3)0.046 (3)0.037 (3)0.005 (2)0.010 (2)0.006 (2)
C30.054 (3)0.075 (4)0.050 (3)0.014 (3)0.005 (2)0.001 (3)
C40.084 (4)0.051 (4)0.059 (4)0.020 (3)0.000 (3)0.006 (3)
C50.085 (4)0.047 (4)0.065 (4)0.001 (3)0.005 (3)0.013 (3)
C60.058 (3)0.046 (3)0.057 (3)0.013 (3)0.005 (2)0.001 (3)
C70.036 (2)0.044 (3)0.036 (2)0.000 (2)0.005 (2)0.002 (2)
C80.037 (2)0.050 (3)0.034 (3)0.004 (2)0.002 (2)0.001 (2)
C90.049 (3)0.069 (4)0.036 (3)0.008 (2)0.004 (2)0.002 (2)
C100.049 (3)0.079 (4)0.049 (3)0.016 (3)0.005 (2)0.020 (3)
C110.054 (3)0.059 (3)0.062 (4)0.017 (3)0.010 (2)0.006 (3)
C120.051 (3)0.057 (3)0.052 (3)0.001 (3)0.002 (2)0.010 (3)
C130.038 (2)0.047 (3)0.040 (3)0.004 (2)0.004 (2)0.003 (2)
C140.048 (3)0.060 (3)0.035 (3)0.003 (2)0.003 (2)0.009 (3)
Geometric parameters (Å, º) top
Br1—C21.885 (4)C5—H30.95
O1—C131.207 (5)C6—H40.95
O2—C141.198 (5)C7—C81.388 (6)
N1—C11.434 (5)C7—C121.378 (6)
N1—C131.405 (6)C7—C131.470 (6)
N1—C141.409 (5)C8—C91.377 (6)
C1—C21.382 (6)C8—C141.475 (7)
C1—C61.387 (6)C9—C101.384 (7)
C2—C31.381 (6)C9—H50.95
C3—C41.377 (7)C10—C111.381 (7)
C3—H10.95C10—H60.95
C4—C51.354 (8)C11—C121.386 (7)
C4—H20.95C11—H70.95
C5—C61.375 (7)C12—H80.95
Br1···O2i3.070 (4)C2···C10ii3.599 (6)
O1···C9ii3.277 (5)C3···C10ii3.561 (7)
O1···C6iii3.367 (6)C8···C11iv3.549 (6)
O1···C10ii3.451 (6)
C1—N1—C13124.5 (3)C12—C7—C13130.7 (4)
C1—N1—C14124.2 (4)C7—C8—C9122.1 (4)
C13—N1—C14111.4 (4)C7—C8—C14108.5 (4)
N1—C1—C2121.0 (4)C9—C8—C14129.4 (4)
N1—C1—C6119.0 (4)C8—C9—C10116.8 (4)
C2—C1—C6119.9 (4)C8—C9—H5121.6
Br1—C2—C1121.1 (3)C10—C9—H5121.6
Br1—C2—C3119.7 (4)C9—C10—C11121.7 (4)
C1—C2—C3119.2 (4)C9—C10—H6119.2
C2—C3—C4120.3 (5)C11—C10—H6119.1
C2—C3—H1119.9C10—C11—C12121.0 (5)
C4—C3—H1119.9C10—C11—H7119.5
C3—C4—C5120.3 (5)C12—C11—H7119.5
C3—C4—H2119.8C7—C12—C11117.7 (4)
C5—C4—H2119.8C7—C12—H8121.1
C4—C5—C6120.6 (5)C11—C12—H8121.1
C4—C5—H3119.7O1—C13—N1124.7 (4)
C6—C5—H3119.7O1—C13—C7129.4 (4)
C1—C6—C5119.7 (4)N1—C13—C7105.9 (4)
C1—C6—H4120.2O2—C14—N1124.1 (4)
C5—C6—H4120.2O2—C14—C8130.2 (4)
C8—C7—C12120.7 (4)N1—C14—C8105.7 (4)
C8—C7—C13108.6 (4)
Symmetry codes: (i) x+3/2, y+1/2, z+3/2; (ii) x1/2, y+1/2, z1/2; (iii) x+2, y, z+1; (iv) x+5/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC14H8BrNO2
Mr302.11
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)11.330 (1), 8.100 (1), 13.965 (1)
β (°) 104.096 (9)
V3)1243.0 (2)
Z4
Radiation typeMo Kα
µ (mm1)3.30
Crystal size (mm)0.60 × 0.56 × 0.48
Data collection
DiffractometerRigaku AFC-7S
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(North et al., 1968)
Tmin, Tmax0.155, 0.200
No. of measured, independent and
observed [I > σ(I)] reflections
3208, 2852, 1882
Rint0.059
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.054, 1.58
No. of reflections1882
No. of parameters163
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.78, 0.73

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1992-1997), SIR92 (Altmare et al., 1993), TEXSAN.

Selected geometric parameters (Å, º) top
Br1—C21.885 (4)C4—C51.354 (8)
O1—C131.207 (5)C5—C61.375 (7)
O2—C141.198 (5)C7—C81.388 (6)
N1—C11.434 (5)C7—C121.378 (6)
N1—C131.405 (6)C7—C131.470 (6)
N1—C141.409 (5)C8—C91.377 (6)
C1—C21.382 (6)C8—C141.475 (7)
C1—C61.387 (6)C9—C101.384 (7)
C2—C31.381 (6)C10—C111.381 (7)
C3—C41.377 (7)C11—C121.386 (7)
C1—N1—C13124.5 (3)C12—C7—C13130.7 (4)
C1—N1—C14124.2 (4)C7—C8—C9122.1 (4)
C13—N1—C14111.4 (4)C7—C8—C14108.5 (4)
N1—C1—C2121.0 (4)C9—C8—C14129.4 (4)
N1—C1—C6119.0 (4)C8—C9—C10116.8 (4)
C2—C1—C6119.9 (4)C9—C10—C11121.7 (4)
Br1—C2—C1121.1 (3)C10—C11—C12121.0 (5)
Br1—C2—C3119.7 (4)C7—C12—C11117.7 (4)
C1—C2—C3119.2 (4)O1—C13—N1124.7 (4)
C2—C3—C4120.3 (5)O1—C13—C7129.4 (4)
C3—C4—C5120.3 (5)N1—C13—C7105.9 (4)
C4—C5—C6120.6 (5)O2—C14—N1124.1 (4)
C1—C6—C5119.7 (4)O2—C14—C8130.2 (4)
C8—C7—C12120.7 (4)N1—C14—C8105.7 (4)
C8—C7—C13108.6 (4)
 

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