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
CCDC reference: 180806
Key indicators
- Single-crystal X-ray study
- T = 180 K
- Mean (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
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.
Crystal data top
C10H4N2O4·2C2H6OS | F(000) = 388 |
Mr = 372.41 | Dx = 1.489 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
a = 12.4152 (11) Å | Cell parameters from 2650 reflections |
b = 5.3266 (2) Å | θ = 1.0–27.5° |
c = 13.8046 (12) Å | µ = 0.35 mm−1 |
β = 114.533 (3)° | T = 180 K |
V = 830.49 (11) Å3 | Block, colourless |
Z = 2 | 0.23 × 0.23 × 0.12 mm |
Data collection top
Nonius KappaCCD diffractometer | 1886 independent reflections |
Radiation source: fine-focus sealed tube | 1302 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Thin–slice ω and φ scans | θmax = 27.5°, θmin = 3.6° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | h = −16→15 |
Tmin = 0.879, Tmax = 0.958 | k = −5→6 |
5086 measured reflections | l = −17→17 |
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)] = 0.045 | H 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 reflections | Δρmax = 0.27 e Å−3 |
116 parameters | Δρmin = −0.39 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: 0.038 (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 | x | y | z | Uiso*/Ueq | |
O1 | 0.74567 (13) | 0.4188 (3) | 0.99846 (12) | 0.0409 (4) | |
O2 | 0.58360 (13) | −0.2608 (2) | 0.78531 (11) | 0.0373 (4) | |
N1 | 0.68411 (17) | 0.0871 (3) | 0.88052 (15) | 0.0288 (5) | |
H1N | 0.728 (2) | 0.099 (4) | 0.8525 (19) | 0.052 (9)* | |
C1 | 0.44894 (17) | −0.2149 (4) | 0.93285 (15) | 0.0272 (5) | |
H1A | 0.4153 | −0.3562 | 0.8886 | 0.033* | |
C2 | 0.53806 (17) | −0.0711 (3) | 0.92499 (15) | 0.0231 (5) | |
C3 | 0.58718 (18) | 0.1363 (3) | 0.98959 (15) | 0.0238 (5) | |
C4 | 0.68134 (19) | 0.2400 (4) | 0.96000 (16) | 0.0275 (5) | |
C5 | 0.59996 (19) | −0.1032 (3) | 0.85297 (16) | 0.0274 (5) | |
S1 | 0.90987 (5) | −0.12410 (9) | 0.77966 (5) | 0.0321 (2) | |
O3 | 0.85097 (14) | 0.1105 (2) | 0.79649 (13) | 0.0387 (4) | |
C6 | 0.9484 (2) | −0.3077 (4) | 0.89650 (18) | 0.0431 (6) | |
H6A | 1.0118 | −0.2239 | 0.9563 | 0.065* | |
H6B | 0.9757 | −0.4733 | 0.8853 | 0.065* | |
H6C | 0.8789 | −0.3275 | 0.9124 | 0.065* | |
C7 | 0.7961 (2) | −0.3210 (4) | 0.69285 (17) | 0.0345 (6) | |
H7A | 0.7614 | −0.2460 | 0.6216 | 0.052* | |
H7B | 0.7347 | −0.3400 | 0.7196 | 0.052* | |
H7C | 0.8291 | −0.4860 | 0.6892 | 0.052* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0417 (11) | 0.0417 (8) | 0.0454 (10) | −0.0167 (8) | 0.0243 (9) | −0.0139 (7) |
O2 | 0.0414 (10) | 0.0400 (9) | 0.0378 (10) | −0.0057 (7) | 0.0235 (8) | −0.0137 (7) |
N1 | 0.0299 (12) | 0.0321 (10) | 0.0318 (11) | −0.0017 (8) | 0.0202 (9) | −0.0043 (8) |
C1 | 0.0258 (13) | 0.0260 (10) | 0.0280 (12) | −0.0010 (9) | 0.0094 (10) | −0.0048 (9) |
C2 | 0.0227 (12) | 0.0236 (10) | 0.0235 (11) | 0.0045 (8) | 0.0100 (9) | 0.0020 (8) |
C3 | 0.0226 (12) | 0.0243 (11) | 0.0243 (11) | 0.0012 (8) | 0.0096 (10) | 0.0016 (8) |
C4 | 0.0291 (13) | 0.0271 (11) | 0.0265 (12) | 0.0019 (10) | 0.0117 (10) | 0.0011 (9) |
C5 | 0.0267 (13) | 0.0291 (11) | 0.0272 (12) | 0.0040 (9) | 0.0119 (10) | 0.0012 (9) |
S1 | 0.0352 (4) | 0.0268 (3) | 0.0446 (4) | −0.0020 (2) | 0.0269 (3) | −0.0019 (2) |
O3 | 0.0546 (11) | 0.0193 (7) | 0.0604 (11) | 0.0006 (6) | 0.0421 (10) | −0.0010 (6) |
C6 | 0.0470 (16) | 0.0401 (12) | 0.0370 (15) | 0.0061 (11) | 0.0121 (12) | −0.0009 (11) |
C7 | 0.0392 (14) | 0.0283 (11) | 0.0354 (13) | 0.0022 (10) | 0.0148 (11) | 0.0014 (9) |
Geometric parameters (Å, º) top
O1—C4 | 1.214 (2) | C3—C4 | 1.495 (3) |
O2—C5 | 1.209 (2) | S1—O3 | 1.5137 (14) |
N1—C4 | 1.378 (3) | S1—C7 | 1.768 (2) |
N1—C5 | 1.391 (3) | S1—C6 | 1.774 (2) |
N1—H1N | 0.79 (2) | C6—H6A | 0.980 |
C1—C3i | 1.386 (3) | C6—H6B | 0.980 |
C1—C2 | 1.387 (3) | C6—H6C | 0.980 |
C1—H1A | 0.950 | C7—H7A | 0.980 |
C2—C3 | 1.391 (3) | C7—H7B | 0.980 |
C2—C5 | 1.497 (3) | C7—H7C | 0.980 |
C3—C1i | 1.386 (3) | | |
| | | |
C4—N1—C5 | 112.58 (18) | N1—C5—C2 | 105.65 (17) |
C4—N1—H1N | 126.1 (18) | O3—S1—C7 | 107.03 (10) |
C5—N1—H1N | 121.3 (18) | O3—S1—C6 | 106.30 (10) |
C3i—C1—C2 | 114.71 (18) | C7—S1—C6 | 97.30 (11) |
C3i—C1—H1A | 122.6 | S1—C6—H6A | 109.5 |
C2—C1—H1A | 122.6 | S1—C6—H6B | 109.5 |
C1—C2—C3 | 122.69 (18) | H6A—C6—H6B | 109.5 |
C1—C2—C5 | 129.42 (18) | S1—C6—H6C | 109.5 |
C3—C2—C5 | 107.88 (17) | H6A—C6—H6C | 109.5 |
C1i—C3—C2 | 122.61 (19) | H6B—C6—H6C | 109.5 |
C1i—C3—C4 | 129.76 (18) | S1—C7—H7A | 109.5 |
C2—C3—C4 | 107.61 (17) | S1—C7—H7B | 109.5 |
O1—C4—N1 | 125.6 (2) | H7A—C7—H7B | 109.5 |
O1—C4—C3 | 128.12 (19) | S1—C7—H7C | 109.5 |
N1—C4—C3 | 106.26 (17) | H7A—C7—H7C | 109.5 |
O2—C5—N1 | 125.71 (19) | H7B—C7—H7C | 109.5 |
O2—C5—C2 | 128.63 (19) | | |
| | | |
C3i—C1—C2—C3 | −0.2 (3) | C2—C3—C4—O1 | −179.2 (2) |
C3i—C1—C2—C5 | 178.53 (18) | C1i—C3—C4—N1 | 177.85 (19) |
C1—C2—C3—C1i | 0.2 (3) | C2—C3—C4—N1 | −0.7 (2) |
C5—C2—C3—C1i | −178.76 (17) | C4—N1—C5—O2 | 179.50 (19) |
C1—C2—C3—C4 | 178.90 (18) | C4—N1—C5—C2 | −1.3 (2) |
C5—C2—C3—C4 | 0.0 (2) | C1—C2—C5—O2 | 1.1 (4) |
C5—N1—C4—O1 | 179.79 (19) | C3—C2—C5—O2 | 179.9 (2) |
C5—N1—C4—C3 | 1.3 (2) | C1—C2—C5—N1 | −178.0 (2) |
C1i—C3—C4—O1 | −0.6 (4) | C3—C2—C5—N1 | 0.8 (2) |
Symmetry code: (i) −x+1, −y, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O3 | 0.79 (2) | 1.98 (2) | 2.765 (2) | 174 (2) |