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organic compounds
The benzene and phthalimido portions of the molecule of N-(3-bromophenyl)phthalimide, C14H8BrNO2, are twisted by 38.1 (1) Å; two molecules are linked across a center of inversion by BrO interactions of length 3.093 (3) Å.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804009547/bt6450sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804009547/bt6450Isup2.hkl |
CCDC reference: 239277
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.036
- wR factor = 0.075
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O1 .. 3.09 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: CAD-4-PC (Kretschmar, 1994); cell refinement: CAD-4 VAX/PC Fortran System (Enraf-Nonius, 1988); data reduction: XCAD4 (Harms, 1997) in WinGX (Farrugia, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
N-(3-Bromophenyl)phthalimide top
Crystal data top
C14H8BrNO2 | F(000) = 600 |
Mr = 302.12 | Dx = 1.712 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 12.025 (1) Å | θ = 5.4–12.5° |
b = 7.877 (1) Å | µ = 3.50 mm−1 |
c = 12.877 (1) Å | T = 298 K |
β = 106.03 (1)° | Block, colorless |
V = 1172.3 (1) Å3 | 0.4 × 0.4 × 0.3 mm |
Z = 4 |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 1433 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
ω–2θ scans | h = 0→14 |
Absorption correction: empirical (using intensity measurements) via ψ scan (North et al., 1968) | k = −9→0 |
Tmin = 0.269, Tmax = 0.350 | l = −15→14 |
2160 measured reflections | 3 standard reflections every 60 min |
2054 independent reflections | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.075 | w = 1/[σ2(Fo2) + (0.0304P)2 + 0.8453P] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max = 0.001 |
2054 reflections | Δρmax = 0.27 e Å−3 |
164 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0194 (10) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Br1 | 0.37323 (4) | 0.09160 (6) | 0.36452 (3) | 0.0597 (2) | |
O1 | 0.5751 (2) | 0.2055 (4) | 0.7722 (2) | 0.0628 (8) | |
O2 | 0.2466 (2) | 0.4974 (4) | 0.7741 (2) | 0.0574 (8) | |
N1 | 0.4052 (2) | 0.3600 (3) | 0.7447 (2) | 0.0386 (7) | |
C1 | 0.3666 (3) | 0.2786 (5) | 0.4557 (3) | 0.042 (1) | |
C2 | 0.3836 (3) | 0.2502 (5) | 0.5648 (3) | 0.040 (1) | |
C3 | 0.3835 (3) | 0.3874 (5) | 0.6308 (2) | 0.038 (1) | |
C4 | 0.3648 (3) | 0.5494 (5) | 0.5896 (3) | 0.047 (1) | |
C5 | 0.3468 (3) | 0.5730 (5) | 0.4795 (3) | 0.053 (1) | |
C6 | 0.3473 (3) | 0.4375 (5) | 0.4122 (3) | 0.050 (1) | |
C7 | 0.5006 (3) | 0.2655 (5) | 0.8059 (3) | 0.043 (1) | |
C8 | 0.4876 (3) | 0.2638 (4) | 0.9176 (3) | 0.040 (1) | |
C9 | 0.5567 (3) | 0.1907 (5) | 1.0102 (3) | 0.051 (1) | |
C10 | 0.5231 (4) | 0.2110 (5) | 1.1043 (3) | 0.057 (1) | |
C11 | 0.4258 (4) | 0.3017 (6) | 1.1047 (3) | 0.058 (2) | |
C12 | 0.3568 (3) | 0.3769 (5) | 1.0116 (3) | 0.051 (1) | |
C13 | 0.3895 (3) | 0.3535 (4) | 0.9180 (3) | 0.038 (1) | |
C14 | 0.3342 (3) | 0.4173 (5) | 0.8072 (3) | 0.042 (1) | |
H2 | 0.3948 | 0.1408 | 0.5930 | 0.048* | |
H4 | 0.3642 | 0.6413 | 0.6348 | 0.056* | |
H5 | 0.3343 | 0.6819 | 0.4507 | 0.063* | |
H6 | 0.3346 | 0.4539 | 0.3383 | 0.060* | |
H9 | 0.6230 | 0.1303 | 1.0098 | 0.061* | |
H10 | 0.5673 | 0.1624 | 1.1682 | 0.068* | |
H11 | 0.4055 | 0.3131 | 1.1690 | 0.069* | |
H12 | 0.2917 | 0.4401 | 1.0123 | 0.061* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0763 (3) | 0.0682 (3) | 0.0377 (2) | −0.0010 (3) | 0.0210 (2) | −0.0095 (2) |
O1 | 0.052 (2) | 0.085 (2) | 0.050 (2) | 0.026 (2) | 0.013 (1) | −0.009 (2) |
O2 | 0.047 (2) | 0.077 (2) | 0.047 (2) | 0.016 (2) | 0.010 (1) | −0.006 (2) |
N1 | 0.041 (2) | 0.043 (2) | 0.031 (1) | 0.004 (1) | 0.009 (1) | −0.004 (1) |
C1 | 0.040 (2) | 0.052 (2) | 0.033 (2) | 0.001 (2) | 0.011 (2) | −0.002 (2) |
C2 | 0.041 (2) | 0.044 (2) | 0.037 (2) | −0.003 (2) | 0.012 (2) | 0.001 (2) |
C3 | 0.034 (2) | 0.047 (2) | 0.033 (2) | 0.000 (2) | 0.010 (1) | −0.002 (2) |
C4 | 0.050 (2) | 0.045 (3) | 0.046 (2) | 0.005 (2) | 0.016 (2) | −0.002 (2) |
C5 | 0.053 (2) | 0.050 (3) | 0.057 (2) | 0.010 (2) | 0.018 (2) | 0.018 (2) |
C6 | 0.048 (2) | 0.066 (3) | 0.038 (2) | 0.010 (2) | 0.015 (2) | 0.009 (2) |
C7 | 0.045 (2) | 0.040 (2) | 0.041 (2) | −0.001 (2) | 0.007 (2) | −0.007 (2) |
C8 | 0.046 (2) | 0.036 (2) | 0.036 (2) | −0.005 (2) | 0.007 (2) | −0.006 (2) |
C9 | 0.057 (3) | 0.039 (2) | 0.050 (2) | −0.005 (2) | 0.003 (2) | −0.001 (2) |
C10 | 0.075 (3) | 0.049 (3) | 0.037 (2) | −0.016 (2) | −0.002 (2) | 0.005 (2) |
C11 | 0.075 (3) | 0.059 (3) | 0.038 (2) | −0.021 (3) | 0.017 (2) | −0.002 (2) |
C12 | 0.055 (2) | 0.057 (3) | 0.043 (2) | −0.007 (2) | 0.017 (2) | −0.006 (2) |
C13 | 0.043 (2) | 0.037 (2) | 0.034 (2) | −0.009 (2) | 0.008 (2) | −0.006 (2) |
C14 | 0.040 (2) | 0.045 (2) | 0.042 (2) | −0.007 (2) | 0.012 (2) | −0.009 (2) |
Geometric parameters (Å, º) top
Br1—C1 | 1.899 (4) | C8—C9 | 1.377 (5) |
O1—C7 | 1.196 (4) | C9—C10 | 1.387 (5) |
O2—C14 | 1.201 (4) | C10—C11 | 1.372 (6) |
N1—C14 | 1.400 (4) | C11—C12 | 1.388 (5) |
N1—C7 | 1.411 (4) | C12—C13 | 1.379 (5) |
N1—C3 | 1.433 (4) | C13—C14 | 1.486 (5) |
C1—C6 | 1.365 (5) | C2—H2 | 0.93 |
C1—C2 | 1.380 (4) | C4—H4 | 0.93 |
C2—C3 | 1.375 (5) | C5—H5 | 0.93 |
C3—C4 | 1.376 (5) | C6—H6 | 0.93 |
C4—C5 | 1.387 (5) | C9—H9 | 0.93 |
C5—C6 | 1.375 (5) | C10—H10 | 0.93 |
C7—C8 | 1.489 (5) | C11—H11 | 0.93 |
C8—C13 | 1.377 (5) | C12—H12 | 0.93 |
C14—N1—C3 | 124.9 (3) | C12—C13—C8 | 121.6 (3) |
C14—N1—C7 | 112.3 (3) | C12—C13—C14 | 129.4 (3) |
C3—N1—C7 | 122.8 (3) | C8—C13—C14 | 109.0 (3) |
C2—C1—C6 | 121.8 (3) | O2—C14—N1 | 125.5 (3) |
C6—C1—Br1 | 119.3 (3) | O2—C14—C13 | 129.4 (3) |
C2—C1—Br1 | 118.9 (3) | N1—C14—C13 | 105.1 (3) |
C1—C2—C3 | 118.4 (3) | C3—C2—H2 | 120.8 |
C2—C3—C4 | 121.3 (3) | C1—C2—H2 | 120.8 |
C2—C3—N1 | 118.9 (3) | C3—C4—H4 | 120.6 |
C4—C3—N1 | 119.8 (3) | C5—C4—H4 | 120.6 |
C3—C4—C5 | 118.7 (3) | C6—C5—H5 | 119.6 |
C4—C5—C6 | 120.9 (4) | C4—C5—H5 | 119.6 |
C1—C6—C5 | 118.9 (3) | C1—C6—H6 | 120.6 |
O1—C7—N1 | 125.5 (3) | C5—C6—H6 | 120.6 |
O1—C7—C8 | 129.5 (3) | C10—C9—H9 | 121.4 |
N1—C7—C8 | 105.0 (3) | C8—C9—H9 | 121.4 |
C7—C8—C9 | 129.9 (4) | C11—C10—H10 | 119.4 |
C7—C8—C13 | 108.5 (3) | C9—C10—H10 | 119.4 |
C9—C8—C13 | 121.6 (3) | C10—C11—H11 | 119.1 |
C8—C9—C10 | 117.2 (4) | C12—C11—H11 | 119.1 |
C9—C10—C11 | 121.1 (4) | C13—C12—H12 | 121.6 |
C10—C11—C12 | 121.7 (4) | C11—C12—H12 | 121.6 |
C11—C12—C13 | 116.8 (4) | ||
C6—C1—C2—C3 | −1.5 (5) | N1—C7—C8—C9 | −179.5 (4) |
Br1—C1—C2—C3 | 177.2 (3) | C13—C8—C9—C10 | 0.1 (5) |
C1—C2—C3—C4 | 1.2 (5) | C7—C8—C9—C10 | 179.5 (3) |
C1—C2—C3—N1 | −177.8 (3) | C8—C9—C10—C11 | −0.7 (6) |
C14—N1—C3—C4 | 53.5 (5) | C9—C10—C11—C12 | 0.0 (6) |
C7—N1—C3—C4 | −128.8 (4) | C10—C11—C12—C13 | 1.2 (6) |
C14—N1—C3—C2 | −127.4 (4) | C11—C12—C13—C8 | −1.7 (5) |
C7—N1—C3—C2 | 50.3 (5) | C11—C12—C13—C14 | −179.9 (4) |
C2—C3—C4—C5 | −0.6 (5) | C9—C8—C13—C12 | 1.1 (5) |
N1—C3—C4—C5 | 178.4 (3) | C7—C8—C13—C12 | −178.4 (3) |
C3—C4—C5—C6 | 0.2 (6) | C9—C8—C13—C14 | 179.6 (3) |
C2—C1—C6—C5 | 1.1 (6) | C7—C8—C13—C14 | 0.1 (4) |
Br1—C1—C6—C5 | −177.6 (3) | C7—N1—C14—O2 | −178.5 (4) |
C4—C5—C6—C1 | −0.4 (6) | C3—N1—C14—O2 | −0.5 (6) |
C14—N1—C7—O1 | −178.4 (4) | C7—N1—C14—C13 | 0.1 (4) |
C3—N1—C7—O1 | 3.6 (6) | C3—N1—C14—C13 | 178.0 (3) |
C14—N1—C7—C8 | 0.0 (4) | C12—C13—C14—O2 | −3.3 (6) |
C3—N1—C7—C8 | −178.0 (3) | C8—C13—C14—O2 | 178.4 (4) |
O1—C7—C8—C13 | 178.3 (4) | C12—C13—C14—N1 | 178.3 (3) |
N1—C7—C8—C13 | 0.0 (4) | C8—C13—C14—N1 | −0.1 (4) |
O1—C7—C8—C9 | −1.2 (7) |
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