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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 Br...O interactions of length 3.093 (3) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804009547/bt6450sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804009547/bt6450Isup2.hkl
Contains datablock I

CCDC reference: 239277

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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
C14H8BrNO2F(000) = 600
Mr = 302.12Dx = 1.712 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 12.025 (1) Åθ = 5.4–12.5°
b = 7.877 (1) ŵ = 3.50 mm1
c = 12.877 (1) ÅT = 298 K
β = 106.03 (1)°Block, colorless
V = 1172.3 (1) Å30.4 × 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 tubeRint = 0.020
Graphite monochromatorθmax = 25.0°, θmin = 2.1°
ω–2θ scansh = 014
Absorption correction: empirical (using intensity measurements)
via ψ scan (North et al., 1968)
k = 90
Tmin = 0.269, Tmax = 0.350l = 1514
2160 measured reflections3 standard reflections every 60 min
2054 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-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 reflectionsΔρmax = 0.27 e Å3
164 parametersΔρmin = 0.32 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0194 (10)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.37323 (4)0.09160 (6)0.36452 (3)0.0597 (2)
O10.5751 (2)0.2055 (4)0.7722 (2)0.0628 (8)
O20.2466 (2)0.4974 (4)0.7741 (2)0.0574 (8)
N10.4052 (2)0.3600 (3)0.7447 (2)0.0386 (7)
C10.3666 (3)0.2786 (5)0.4557 (3)0.042 (1)
C20.3836 (3)0.2502 (5)0.5648 (3)0.040 (1)
C30.3835 (3)0.3874 (5)0.6308 (2)0.038 (1)
C40.3648 (3)0.5494 (5)0.5896 (3)0.047 (1)
C50.3468 (3)0.5730 (5)0.4795 (3)0.053 (1)
C60.3473 (3)0.4375 (5)0.4122 (3)0.050 (1)
C70.5006 (3)0.2655 (5)0.8059 (3)0.043 (1)
C80.4876 (3)0.2638 (4)0.9176 (3)0.040 (1)
C90.5567 (3)0.1907 (5)1.0102 (3)0.051 (1)
C100.5231 (4)0.2110 (5)1.1043 (3)0.057 (1)
C110.4258 (4)0.3017 (6)1.1047 (3)0.058 (2)
C120.3568 (3)0.3769 (5)1.0116 (3)0.051 (1)
C130.3895 (3)0.3535 (4)0.9180 (3)0.038 (1)
C140.3342 (3)0.4173 (5)0.8072 (3)0.042 (1)
H20.39480.14080.59300.048*
H40.36420.64130.63480.056*
H50.33430.68190.45070.063*
H60.33460.45390.33830.060*
H90.62300.13031.00980.061*
H100.56730.16241.16820.068*
H110.40550.31311.16900.069*
H120.29170.44011.01230.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0763 (3)0.0682 (3)0.0377 (2)0.0010 (3)0.0210 (2)0.0095 (2)
O10.052 (2)0.085 (2)0.050 (2)0.026 (2)0.013 (1)0.009 (2)
O20.047 (2)0.077 (2)0.047 (2)0.016 (2)0.010 (1)0.006 (2)
N10.041 (2)0.043 (2)0.031 (1)0.004 (1)0.009 (1)0.004 (1)
C10.040 (2)0.052 (2)0.033 (2)0.001 (2)0.011 (2)0.002 (2)
C20.041 (2)0.044 (2)0.037 (2)0.003 (2)0.012 (2)0.001 (2)
C30.034 (2)0.047 (2)0.033 (2)0.000 (2)0.010 (1)0.002 (2)
C40.050 (2)0.045 (3)0.046 (2)0.005 (2)0.016 (2)0.002 (2)
C50.053 (2)0.050 (3)0.057 (2)0.010 (2)0.018 (2)0.018 (2)
C60.048 (2)0.066 (3)0.038 (2)0.010 (2)0.015 (2)0.009 (2)
C70.045 (2)0.040 (2)0.041 (2)0.001 (2)0.007 (2)0.007 (2)
C80.046 (2)0.036 (2)0.036 (2)0.005 (2)0.007 (2)0.006 (2)
C90.057 (3)0.039 (2)0.050 (2)0.005 (2)0.003 (2)0.001 (2)
C100.075 (3)0.049 (3)0.037 (2)0.016 (2)0.002 (2)0.005 (2)
C110.075 (3)0.059 (3)0.038 (2)0.021 (3)0.017 (2)0.002 (2)
C120.055 (2)0.057 (3)0.043 (2)0.007 (2)0.017 (2)0.006 (2)
C130.043 (2)0.037 (2)0.034 (2)0.009 (2)0.008 (2)0.006 (2)
C140.040 (2)0.045 (2)0.042 (2)0.007 (2)0.012 (2)0.009 (2)
Geometric parameters (Å, º) top
Br1—C11.899 (4)C8—C91.377 (5)
O1—C71.196 (4)C9—C101.387 (5)
O2—C141.201 (4)C10—C111.372 (6)
N1—C141.400 (4)C11—C121.388 (5)
N1—C71.411 (4)C12—C131.379 (5)
N1—C31.433 (4)C13—C141.486 (5)
C1—C61.365 (5)C2—H20.93
C1—C21.380 (4)C4—H40.93
C2—C31.375 (5)C5—H50.93
C3—C41.376 (5)C6—H60.93
C4—C51.387 (5)C9—H90.93
C5—C61.375 (5)C10—H100.93
C7—C81.489 (5)C11—H110.93
C8—C131.377 (5)C12—H120.93
C14—N1—C3124.9 (3)C12—C13—C8121.6 (3)
C14—N1—C7112.3 (3)C12—C13—C14129.4 (3)
C3—N1—C7122.8 (3)C8—C13—C14109.0 (3)
C2—C1—C6121.8 (3)O2—C14—N1125.5 (3)
C6—C1—Br1119.3 (3)O2—C14—C13129.4 (3)
C2—C1—Br1118.9 (3)N1—C14—C13105.1 (3)
C1—C2—C3118.4 (3)C3—C2—H2120.8
C2—C3—C4121.3 (3)C1—C2—H2120.8
C2—C3—N1118.9 (3)C3—C4—H4120.6
C4—C3—N1119.8 (3)C5—C4—H4120.6
C3—C4—C5118.7 (3)C6—C5—H5119.6
C4—C5—C6120.9 (4)C4—C5—H5119.6
C1—C6—C5118.9 (3)C1—C6—H6120.6
O1—C7—N1125.5 (3)C5—C6—H6120.6
O1—C7—C8129.5 (3)C10—C9—H9121.4
N1—C7—C8105.0 (3)C8—C9—H9121.4
C7—C8—C9129.9 (4)C11—C10—H10119.4
C7—C8—C13108.5 (3)C9—C10—H10119.4
C9—C8—C13121.6 (3)C10—C11—H11119.1
C8—C9—C10117.2 (4)C12—C11—H11119.1
C9—C10—C11121.1 (4)C13—C12—H12121.6
C10—C11—C12121.7 (4)C11—C12—H12121.6
C11—C12—C13116.8 (4)
C6—C1—C2—C31.5 (5)N1—C7—C8—C9179.5 (4)
Br1—C1—C2—C3177.2 (3)C13—C8—C9—C100.1 (5)
C1—C2—C3—C41.2 (5)C7—C8—C9—C10179.5 (3)
C1—C2—C3—N1177.8 (3)C8—C9—C10—C110.7 (6)
C14—N1—C3—C453.5 (5)C9—C10—C11—C120.0 (6)
C7—N1—C3—C4128.8 (4)C10—C11—C12—C131.2 (6)
C14—N1—C3—C2127.4 (4)C11—C12—C13—C81.7 (5)
C7—N1—C3—C250.3 (5)C11—C12—C13—C14179.9 (4)
C2—C3—C4—C50.6 (5)C9—C8—C13—C121.1 (5)
N1—C3—C4—C5178.4 (3)C7—C8—C13—C12178.4 (3)
C3—C4—C5—C60.2 (6)C9—C8—C13—C14179.6 (3)
C2—C1—C6—C51.1 (6)C7—C8—C13—C140.1 (4)
Br1—C1—C6—C5177.6 (3)C7—N1—C14—O2178.5 (4)
C4—C5—C6—C10.4 (6)C3—N1—C14—O20.5 (6)
C14—N1—C7—O1178.4 (4)C7—N1—C14—C130.1 (4)
C3—N1—C7—O13.6 (6)C3—N1—C14—C13178.0 (3)
C14—N1—C7—C80.0 (4)C12—C13—C14—O23.3 (6)
C3—N1—C7—C8178.0 (3)C8—C13—C14—O2178.4 (4)
O1—C7—C8—C13178.3 (4)C12—C13—C14—N1178.3 (3)
N1—C7—C8—C130.0 (4)C8—C13—C14—N10.1 (4)
O1—C7—C8—C91.2 (7)
 

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