Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802020263/ww6049sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802020263/ww6049Isup2.hkl |
CCDC reference: 202330
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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%.
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).
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.
C14H8BrNO2 | F(000) = 600.00 |
Mr = 302.11 | Dx = 1.614 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2yn | Cell parameters from 19 reflections |
a = 11.330 (1) Å | θ = 5.4–7.8° |
b = 8.100 (1) Å | µ = 3.30 mm−1 |
c = 13.965 (1) Å | T = 298 K |
β = 104.096 (9)° | Prism, colorless |
V = 1243.0 (2) Å3 | 0.60 × 0.56 × 0.48 mm |
Z = 4 |
Rigaku AFC-7S diffractometer | 1882 reflections with I > σ(I) |
Radiation source: X-ray tube | Rint = 0.059 |
Graphite monochromator | θmax = 27.5°, θmin = 2.1° |
ω–2θ scans | h = 0→14 |
Absorption correction: empirical (using intensity measurements) (North et al., 1968) | k = 0→10 |
Tmin = 0.155, Tmax = 0.200 | l = −18→17 |
3208 measured reflections | 3 standard reflections every 150 reflections |
2852 independent reflections | intensity decay: −0.2% |
Refinement on F | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.068 | H-atom parameters constrained |
wR(F2) = 0.054 | Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.00022|Fo|2] |
S = 1.58 | (Δ/σ)max = 0.007 |
1882 reflections | Δρmax = 0.78 e Å−3 |
163 parameters | Δρmin = −0.73 e Å−3 |
C14H8BrNO2 | V = 1243.0 (2) Å3 |
Mr = 302.11 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.330 (1) Å | µ = 3.30 mm−1 |
b = 8.100 (1) Å | T = 298 K |
c = 13.965 (1) Å | 0.60 × 0.56 × 0.48 mm |
β = 104.096 (9)° |
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 = 0.200 | 3 standard reflections every 150 reflections |
3208 measured reflections | intensity decay: −0.2% |
2852 independent reflections |
R[F2 > 2σ(F2)] = 0.068 | 0 restraints |
wR(F2) = 0.054 | H-atom parameters constrained |
S = 1.58 | Δρmax = 0.78 e Å−3 |
1882 reflections | Δρmin = −0.73 e Å−3 |
163 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.65623 (5) | 0.17246 (8) | 0.65972 (4) | 0.0733 (2) | |
O1 | 0.9013 (3) | 0.2749 (4) | 0.5373 (2) | 0.057 (1) | |
O2 | 0.9976 (3) | −0.0217 (5) | 0.8238 (3) | 0.077 (1) | |
N1 | 0.9286 (3) | 0.0949 (4) | 0.6697 (3) | 0.042 (1) | |
C1 | 0.8461 (4) | −0.0330 (5) | 0.6245 (3) | 0.042 (1) | |
C2 | 0.7222 (4) | −0.0175 (6) | 0.6145 (3) | 0.045 (1) | |
C3 | 0.6458 (4) | −0.1427 (7) | 0.5696 (4) | 0.061 (2) | |
C4 | 0.6928 (6) | −0.2821 (7) | 0.5362 (4) | 0.067 (2) | |
C5 | 0.8143 (6) | −0.2970 (6) | 0.5465 (4) | 0.068 (2) | |
C6 | 0.8923 (4) | −0.1736 (6) | 0.5902 (4) | 0.055 (2) | |
C7 | 1.0394 (3) | 0.3350 (5) | 0.6953 (3) | 0.039 (1) | |
C8 | 1.0691 (4) | 0.2454 (6) | 0.7826 (3) | 0.041 (1) | |
C9 | 1.1545 (4) | 0.3001 (6) | 0.8642 (3) | 0.053 (1) | |
C10 | 1.2065 (4) | 0.4526 (7) | 0.8568 (4) | 0.060 (2) | |
C11 | 1.1761 (4) | 0.5444 (6) | 0.7709 (4) | 0.059 (2) | |
C12 | 1.0931 (4) | 0.4855 (6) | 0.6880 (4) | 0.055 (2) | |
C13 | 0.9490 (4) | 0.2412 (6) | 0.6221 (3) | 0.043 (1) | |
C14 | 0.9992 (4) | 0.0900 (6) | 0.7678 (3) | 0.050 (1) | |
H1 | 0.5604 | −0.1328 | 0.5618 | 0.073* | |
H2 | 0.6398 | −0.3681 | 0.5059 | 0.081* | |
H3 | 0.8459 | −0.3936 | 0.5232 | 0.081* | |
H4 | 0.9774 | −0.1846 | 0.5968 | 0.067* | |
H5 | 1.1765 | 0.2362 | 0.9229 | 0.063* | |
H6 | 1.2647 | 0.4952 | 0.9120 | 0.072* | |
H7 | 1.2124 | 0.6496 | 0.7687 | 0.071* | |
H8 | 1.0741 | 0.5468 | 0.6282 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0642 (4) | 0.0854 (5) | 0.0730 (4) | 0.0066 (3) | 0.0218 (3) | −0.0266 (4) |
O1 | 0.064 (2) | 0.061 (2) | 0.034 (2) | −0.008 (2) | −0.009 (2) | 0.009 (2) |
O2 | 0.092 (3) | 0.073 (3) | 0.051 (2) | −0.027 (2) | −0.014 (2) | 0.025 (2) |
N1 | 0.046 (2) | 0.043 (2) | 0.032 (2) | −0.005 (2) | −0.001 (2) | 0.005 (2) |
C1 | 0.047 (2) | 0.041 (3) | 0.033 (2) | −0.005 (2) | 0.002 (2) | 0.004 (2) |
C2 | 0.052 (3) | 0.046 (3) | 0.037 (3) | −0.005 (2) | 0.010 (2) | −0.006 (2) |
C3 | 0.054 (3) | 0.075 (4) | 0.050 (3) | −0.014 (3) | 0.005 (2) | −0.001 (3) |
C4 | 0.084 (4) | 0.051 (4) | 0.059 (4) | −0.020 (3) | 0.000 (3) | −0.006 (3) |
C5 | 0.085 (4) | 0.047 (4) | 0.065 (4) | 0.001 (3) | 0.005 (3) | −0.013 (3) |
C6 | 0.058 (3) | 0.046 (3) | 0.057 (3) | 0.013 (3) | 0.005 (2) | 0.001 (3) |
C7 | 0.036 (2) | 0.044 (3) | 0.036 (2) | 0.000 (2) | 0.005 (2) | −0.002 (2) |
C8 | 0.037 (2) | 0.050 (3) | 0.034 (3) | −0.004 (2) | 0.002 (2) | −0.001 (2) |
C9 | 0.049 (3) | 0.069 (4) | 0.036 (3) | −0.008 (2) | 0.004 (2) | 0.002 (2) |
C10 | 0.049 (3) | 0.079 (4) | 0.049 (3) | −0.016 (3) | 0.005 (2) | −0.020 (3) |
C11 | 0.054 (3) | 0.059 (3) | 0.062 (4) | −0.017 (3) | 0.010 (2) | −0.006 (3) |
C12 | 0.051 (3) | 0.057 (3) | 0.052 (3) | 0.001 (3) | 0.002 (2) | 0.010 (3) |
C13 | 0.038 (2) | 0.047 (3) | 0.040 (3) | 0.004 (2) | 0.004 (2) | 0.003 (2) |
C14 | 0.048 (3) | 0.060 (3) | 0.035 (3) | −0.003 (2) | −0.003 (2) | 0.009 (3) |
Br1—C2 | 1.885 (4) | C5—H3 | 0.95 |
O1—C13 | 1.207 (5) | C6—H4 | 0.95 |
O2—C14 | 1.198 (5) | C7—C8 | 1.388 (6) |
N1—C1 | 1.434 (5) | C7—C12 | 1.378 (6) |
N1—C13 | 1.405 (6) | C7—C13 | 1.470 (6) |
N1—C14 | 1.409 (5) | C8—C9 | 1.377 (6) |
C1—C2 | 1.382 (6) | C8—C14 | 1.475 (7) |
C1—C6 | 1.387 (6) | C9—C10 | 1.384 (7) |
C2—C3 | 1.381 (6) | C9—H5 | 0.95 |
C3—C4 | 1.377 (7) | C10—C11 | 1.381 (7) |
C3—H1 | 0.95 | C10—H6 | 0.95 |
C4—C5 | 1.354 (8) | C11—C12 | 1.386 (7) |
C4—H2 | 0.95 | C11—H7 | 0.95 |
C5—C6 | 1.375 (7) | C12—H8 | 0.95 |
Br1···O2i | 3.070 (4) | C2···C10ii | 3.599 (6) |
O1···C9ii | 3.277 (5) | C3···C10ii | 3.561 (7) |
O1···C6iii | 3.367 (6) | C8···C11iv | 3.549 (6) |
O1···C10ii | 3.451 (6) | ||
C1—N1—C13 | 124.5 (3) | C12—C7—C13 | 130.7 (4) |
C1—N1—C14 | 124.2 (4) | C7—C8—C9 | 122.1 (4) |
C13—N1—C14 | 111.4 (4) | C7—C8—C14 | 108.5 (4) |
N1—C1—C2 | 121.0 (4) | C9—C8—C14 | 129.4 (4) |
N1—C1—C6 | 119.0 (4) | C8—C9—C10 | 116.8 (4) |
C2—C1—C6 | 119.9 (4) | C8—C9—H5 | 121.6 |
Br1—C2—C1 | 121.1 (3) | C10—C9—H5 | 121.6 |
Br1—C2—C3 | 119.7 (4) | C9—C10—C11 | 121.7 (4) |
C1—C2—C3 | 119.2 (4) | C9—C10—H6 | 119.2 |
C2—C3—C4 | 120.3 (5) | C11—C10—H6 | 119.1 |
C2—C3—H1 | 119.9 | C10—C11—C12 | 121.0 (5) |
C4—C3—H1 | 119.9 | C10—C11—H7 | 119.5 |
C3—C4—C5 | 120.3 (5) | C12—C11—H7 | 119.5 |
C3—C4—H2 | 119.8 | C7—C12—C11 | 117.7 (4) |
C5—C4—H2 | 119.8 | C7—C12—H8 | 121.1 |
C4—C5—C6 | 120.6 (5) | C11—C12—H8 | 121.1 |
C4—C5—H3 | 119.7 | O1—C13—N1 | 124.7 (4) |
C6—C5—H3 | 119.7 | O1—C13—C7 | 129.4 (4) |
C1—C6—C5 | 119.7 (4) | N1—C13—C7 | 105.9 (4) |
C1—C6—H4 | 120.2 | O2—C14—N1 | 124.1 (4) |
C5—C6—H4 | 120.2 | O2—C14—C8 | 130.2 (4) |
C8—C7—C12 | 120.7 (4) | N1—C14—C8 | 105.7 (4) |
C8—C7—C13 | 108.6 (4) |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+2, −y, −z+1; (iv) −x+5/2, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C14H8BrNO2 |
Mr | 302.11 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 11.330 (1), 8.100 (1), 13.965 (1) |
β (°) | 104.096 (9) |
V (Å3) | 1243.0 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.30 |
Crystal size (mm) | 0.60 × 0.56 × 0.48 |
Data collection | |
Diffractometer | Rigaku AFC-7S diffractometer |
Absorption correction | Empirical (using intensity measurements) (North et al., 1968) |
Tmin, Tmax | 0.155, 0.200 |
No. of measured, independent and observed [I > σ(I)] reflections | 3208, 2852, 1882 |
Rint | 0.059 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.054, 1.58 |
No. of reflections | 1882 |
No. of parameters | 163 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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.
Br1—C2 | 1.885 (4) | C4—C5 | 1.354 (8) |
O1—C13 | 1.207 (5) | C5—C6 | 1.375 (7) |
O2—C14 | 1.198 (5) | C7—C8 | 1.388 (6) |
N1—C1 | 1.434 (5) | C7—C12 | 1.378 (6) |
N1—C13 | 1.405 (6) | C7—C13 | 1.470 (6) |
N1—C14 | 1.409 (5) | C8—C9 | 1.377 (6) |
C1—C2 | 1.382 (6) | C8—C14 | 1.475 (7) |
C1—C6 | 1.387 (6) | C9—C10 | 1.384 (7) |
C2—C3 | 1.381 (6) | C10—C11 | 1.381 (7) |
C3—C4 | 1.377 (7) | C11—C12 | 1.386 (7) |
C1—N1—C13 | 124.5 (3) | C12—C7—C13 | 130.7 (4) |
C1—N1—C14 | 124.2 (4) | C7—C8—C9 | 122.1 (4) |
C13—N1—C14 | 111.4 (4) | C7—C8—C14 | 108.5 (4) |
N1—C1—C2 | 121.0 (4) | C9—C8—C14 | 129.4 (4) |
N1—C1—C6 | 119.0 (4) | C8—C9—C10 | 116.8 (4) |
C2—C1—C6 | 119.9 (4) | C9—C10—C11 | 121.7 (4) |
Br1—C2—C1 | 121.1 (3) | C10—C11—C12 | 121.0 (5) |
Br1—C2—C3 | 119.7 (4) | C7—C12—C11 | 117.7 (4) |
C1—C2—C3 | 119.2 (4) | O1—C13—N1 | 124.7 (4) |
C2—C3—C4 | 120.3 (5) | O1—C13—C7 | 129.4 (4) |
C3—C4—C5 | 120.3 (5) | N1—C13—C7 | 105.9 (4) |
C4—C5—C6 | 120.6 (5) | O2—C14—N1 | 124.1 (4) |
C1—C6—C5 | 119.7 (4) | O2—C14—C8 | 130.2 (4) |
C8—C7—C12 | 120.7 (4) | N1—C14—C8 | 105.7 (4) |
C8—C7—C13 | 108.6 (4) |
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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)].