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The title compound, C10H6N2O4, belongs to a series of N-aryl­male­imides. These N-substituted male­imides can be used as photo-initiators for free-radical polymerization. The mol­ecule has crystallographic twofold rotation symmetry. The dihedral angle between the planes of the benzene and imide rings is 42.98 (5)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803022426/cf6281sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803022426/cf6281Isup2.hkl
Contains datablock I

CCDC reference: 226980

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.030
  • wR factor = 0.084
  • Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT764_ALERT_4_C Overcomplete CIF Bond list Detected (Rep/Expd) . 1.17 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 SDP (Frenz, 1978); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C10H6N2O4F(000) = 448
Mr = 218.17Dx = 1.543 Mg m3
Monoclinic, C2/cMelting point: 436(1) K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 10.535 (2) ÅCell parameters from 25 reflections
b = 11.624 (3) Åθ = 8–16°
c = 8.148 (2) ŵ = 0.12 mm1
β = 109.69 (3)°T = 293 K
V = 939.5 (4) Å3Prism, colourless
Z = 40.18 × 0.15 × 0.08 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.017
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.7°
Graphite monochromatorh = 012
ω/2θ scansk = 130
870 measured reflectionsl = 99
824 independent reflections3 standard reflections every 120 min
738 reflections with I > 2σ(I) intensity decay: 1.2%
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)] = 0.030H-atom parameters constrained
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0429P)2 + 0.4529P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
824 reflectionsΔρmax = 0.14 e Å3
76 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0169 (18)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.50000.21145 (13)0.25000.0394 (4)
N20.50000.27159 (14)0.25000.0426 (4)
C40.50000.08902 (15)0.25000.0345 (4)
C10.50000.14578 (15)0.25000.0359 (4)
C30.39783 (13)0.03000 (11)0.12627 (18)0.0407 (4)
H30.32940.07030.04380.049*
O20.43544 (12)0.32156 (9)0.11594 (15)0.0611 (4)
C20.39760 (13)0.08862 (12)0.12539 (17)0.0405 (4)
H20.32970.12920.04240.049*
O10.27411 (10)0.24654 (10)0.20227 (15)0.0572 (4)
C50.38614 (15)0.28100 (12)0.22655 (18)0.0441 (4)
C60.43556 (17)0.40155 (13)0.2380 (2)0.0566 (4)
H60.38280.46690.22930.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0392 (8)0.0297 (8)0.0479 (9)0.0000.0128 (7)0.000
N20.0480 (9)0.0326 (9)0.0474 (10)0.0000.0164 (8)0.000
C40.0349 (9)0.0311 (9)0.0402 (9)0.0000.0161 (8)0.000
C10.0399 (10)0.0299 (9)0.0408 (10)0.0000.0175 (8)0.000
C30.0364 (7)0.0370 (8)0.0431 (8)0.0024 (5)0.0062 (6)0.0039 (6)
O20.0801 (8)0.0380 (6)0.0563 (7)0.0050 (5)0.0113 (6)0.0102 (5)
C20.0374 (7)0.0370 (7)0.0428 (7)0.0048 (6)0.0078 (6)0.0020 (6)
O10.0444 (6)0.0538 (7)0.0729 (8)0.0088 (5)0.0189 (5)0.0050 (5)
C50.0481 (8)0.0384 (8)0.0430 (8)0.0079 (6)0.0115 (6)0.0009 (6)
C60.0698 (9)0.0341 (8)0.0570 (9)0.0086 (7)0.0098 (8)0.0023 (7)
Geometric parameters (Å, º) top
N1—C5i1.4052 (17)C1—C21.3777 (16)
N1—C51.4052 (17)C3—C21.379 (2)
N1—C41.423 (2)C3—H30.930
N2—O21.2217 (13)C2—H20.930
N2—O2i1.2217 (13)O1—C51.1979 (18)
N2—C11.462 (2)C5—C61.487 (2)
C4—C31.3835 (16)C6—C6i1.305 (3)
C4—C3i1.3835 (16)C6—H60.930
C1—C2i1.3777 (16)
C5i—N1—C5109.75 (16)C2—C3—C4119.94 (13)
C5i—N1—C4125.12 (8)C2—C3—H3120.0
C5—N1—C4125.12 (8)C4—C3—H3120.0
O2—N2—O2i123.22 (17)C1—C2—C3118.61 (12)
O2—N2—C1118.39 (8)C1—C2—H2120.7
O2i—N2—C1118.39 (8)C3—C2—H2120.7
C3—C4—C3i120.56 (17)O1—C5—N1125.34 (13)
C3—C4—N1119.72 (9)O1—C5—C6129.06 (14)
C3i—C4—N1119.72 (9)N1—C5—C6105.59 (13)
C2i—C1—C2122.33 (17)C6i—C6—C5109.52 (9)
C2i—C1—N2118.83 (9)C6i—C6—H6125.2
C2—C1—N2118.83 (9)C5—C6—H6125.2
C5i—N1—C4—C3136.82 (10)C2i—C1—C2—C30.20 (9)
C5—N1—C4—C343.18 (10)N2—C1—C2—C3179.80 (9)
C5i—N1—C4—C3i43.18 (10)C4—C3—C2—C10.39 (18)
C5—N1—C4—C3i136.82 (10)C5i—N1—C5—O1179.43 (17)
O2—N2—C1—C2i159.26 (10)C4—N1—C5—O10.57 (17)
O2i—N2—C1—C2i20.74 (10)C5i—N1—C5—C60.39 (7)
O2—N2—C1—C220.74 (10)C4—N1—C5—C6179.61 (7)
O2i—N2—C1—C2159.26 (10)O1—C5—C6—C6i178.66 (18)
C3i—C4—C3—C20.20 (9)N1—C5—C6—C6i1.2 (2)
N1—C4—C3—C2179.80 (9)
Symmetry code: (i) x+1, y, z+1/2.
 

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