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Recrystallization of pyromellitic di­imide from di­methyl sulfoxide yields a 1:2 complex, C10H4N2O4·2C2H6SO. In space group P21/c, the di­imide mol­ecules form herring-bone-packed layers and are capped at each end by hydrogen-bonded di­methyl sulfoxide mol­ecules. The 1:2 complex is sited on a crystallographic centre of symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001162/cf6143sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001162/cf6143Isup2.hkl
Contains datablock I

CCDC reference: 180806

Key indicators

  • Single-crystal X-ray study
  • T = 180 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.108
  • Data-to-parameter ratio = 16.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1993) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C10H4N2O4·2C2H6OSF(000) = 388
Mr = 372.41Dx = 1.489 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.7107 Å
a = 12.4152 (11) ÅCell parameters from 2650 reflections
b = 5.3266 (2) Åθ = 1.0–27.5°
c = 13.8046 (12) ŵ = 0.35 mm1
β = 114.533 (3)°T = 180 K
V = 830.49 (11) Å3Block, colourless
Z = 20.23 × 0.23 × 0.12 mm
Data collection top
Nonius KappaCCD
diffractometer
1886 independent reflections
Radiation source: fine-focus sealed tube1302 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Thin–slice ω and φ scansθmax = 27.5°, θmin = 3.6°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
h = 1615
Tmin = 0.879, Tmax = 0.958k = 56
5086 measured reflectionsl = 1717
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)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.0453P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.010
1886 reflectionsΔρmax = 0.27 e Å3
116 parametersΔρmin = 0.39 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.038 (4)
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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.74567 (13)0.4188 (3)0.99846 (12)0.0409 (4)
O20.58360 (13)0.2608 (2)0.78531 (11)0.0373 (4)
N10.68411 (17)0.0871 (3)0.88052 (15)0.0288 (5)
H1N0.728 (2)0.099 (4)0.8525 (19)0.052 (9)*
C10.44894 (17)0.2149 (4)0.93285 (15)0.0272 (5)
H1A0.41530.35620.88860.033*
C20.53806 (17)0.0711 (3)0.92499 (15)0.0231 (5)
C30.58718 (18)0.1363 (3)0.98959 (15)0.0238 (5)
C40.68134 (19)0.2400 (4)0.96000 (16)0.0275 (5)
C50.59996 (19)0.1032 (3)0.85297 (16)0.0274 (5)
S10.90987 (5)0.12410 (9)0.77966 (5)0.0321 (2)
O30.85097 (14)0.1105 (2)0.79649 (13)0.0387 (4)
C60.9484 (2)0.3077 (4)0.89650 (18)0.0431 (6)
H6A1.01180.22390.95630.065*
H6B0.97570.47330.88530.065*
H6C0.87890.32750.91240.065*
C70.7961 (2)0.3210 (4)0.69285 (17)0.0345 (6)
H7A0.76140.24600.62160.052*
H7B0.73470.34000.71960.052*
H7C0.82910.48600.68920.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0417 (11)0.0417 (8)0.0454 (10)0.0167 (8)0.0243 (9)0.0139 (7)
O20.0414 (10)0.0400 (9)0.0378 (10)0.0057 (7)0.0235 (8)0.0137 (7)
N10.0299 (12)0.0321 (10)0.0318 (11)0.0017 (8)0.0202 (9)0.0043 (8)
C10.0258 (13)0.0260 (10)0.0280 (12)0.0010 (9)0.0094 (10)0.0048 (9)
C20.0227 (12)0.0236 (10)0.0235 (11)0.0045 (8)0.0100 (9)0.0020 (8)
C30.0226 (12)0.0243 (11)0.0243 (11)0.0012 (8)0.0096 (10)0.0016 (8)
C40.0291 (13)0.0271 (11)0.0265 (12)0.0019 (10)0.0117 (10)0.0011 (9)
C50.0267 (13)0.0291 (11)0.0272 (12)0.0040 (9)0.0119 (10)0.0012 (9)
S10.0352 (4)0.0268 (3)0.0446 (4)0.0020 (2)0.0269 (3)0.0019 (2)
O30.0546 (11)0.0193 (7)0.0604 (11)0.0006 (6)0.0421 (10)0.0010 (6)
C60.0470 (16)0.0401 (12)0.0370 (15)0.0061 (11)0.0121 (12)0.0009 (11)
C70.0392 (14)0.0283 (11)0.0354 (13)0.0022 (10)0.0148 (11)0.0014 (9)
Geometric parameters (Å, º) top
O1—C41.214 (2)C3—C41.495 (3)
O2—C51.209 (2)S1—O31.5137 (14)
N1—C41.378 (3)S1—C71.768 (2)
N1—C51.391 (3)S1—C61.774 (2)
N1—H1N0.79 (2)C6—H6A0.980
C1—C3i1.386 (3)C6—H6B0.980
C1—C21.387 (3)C6—H6C0.980
C1—H1A0.950C7—H7A0.980
C2—C31.391 (3)C7—H7B0.980
C2—C51.497 (3)C7—H7C0.980
C3—C1i1.386 (3)
C4—N1—C5112.58 (18)N1—C5—C2105.65 (17)
C4—N1—H1N126.1 (18)O3—S1—C7107.03 (10)
C5—N1—H1N121.3 (18)O3—S1—C6106.30 (10)
C3i—C1—C2114.71 (18)C7—S1—C697.30 (11)
C3i—C1—H1A122.6S1—C6—H6A109.5
C2—C1—H1A122.6S1—C6—H6B109.5
C1—C2—C3122.69 (18)H6A—C6—H6B109.5
C1—C2—C5129.42 (18)S1—C6—H6C109.5
C3—C2—C5107.88 (17)H6A—C6—H6C109.5
C1i—C3—C2122.61 (19)H6B—C6—H6C109.5
C1i—C3—C4129.76 (18)S1—C7—H7A109.5
C2—C3—C4107.61 (17)S1—C7—H7B109.5
O1—C4—N1125.6 (2)H7A—C7—H7B109.5
O1—C4—C3128.12 (19)S1—C7—H7C109.5
N1—C4—C3106.26 (17)H7A—C7—H7C109.5
O2—C5—N1125.71 (19)H7B—C7—H7C109.5
O2—C5—C2128.63 (19)
C3i—C1—C2—C30.2 (3)C2—C3—C4—O1179.2 (2)
C3i—C1—C2—C5178.53 (18)C1i—C3—C4—N1177.85 (19)
C1—C2—C3—C1i0.2 (3)C2—C3—C4—N10.7 (2)
C5—C2—C3—C1i178.76 (17)C4—N1—C5—O2179.50 (19)
C1—C2—C3—C4178.90 (18)C4—N1—C5—C21.3 (2)
C5—C2—C3—C40.0 (2)C1—C2—C5—O21.1 (4)
C5—N1—C4—O1179.79 (19)C3—C2—C5—O2179.9 (2)
C5—N1—C4—C31.3 (2)C1—C2—C5—N1178.0 (2)
C1i—C3—C4—O10.6 (4)C3—C2—C5—N10.8 (2)
Symmetry code: (i) x+1, y, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O30.79 (2)1.98 (2)2.765 (2)174 (2)
 

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