organic compounds
The sulfone S atom of the title compound, C26H14N4O6S, lies on a twofold rotation axis. The dihedral angle between the phthalimide unit and the pyridyl ring is 50.2 (1)°.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807007404/sj2224sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807007404/sj2224Isup2.hkl |
CCDC reference: 640496
Computing details top
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).
Bis(1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl) sulfone top
Crystal data top
C26H14N4O6S | F(000) = 1048 |
Mr = 510.47 | Dx = 1.480 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 4168 reflections |
a = 8.1740 (8) Å | θ = 2.4–28.0° |
b = 9.8743 (8) Å | µ = 0.19 mm−1 |
c = 28.662 (3) Å | T = 295 K |
β = 97.977 (2)° | Block, colorless |
V = 2291.0 (4) Å3 | 0.36 × 0.28 × 0.21 mm |
Z = 4 |
Data collection top
Bruker APEX CCD diffractometer | 2243 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 27.5°, θmin = 1.4° |
φ and ω scans | h = −10→9 |
6468 measured reflections | k = −12→12 |
2570 independent reflections | l = −36→31 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | All H-atom parameters refined |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0731P)2 + 0.7633P] where P = (Fo2 + 2Fc2)/3 |
2570 reflections | (Δ/σ)max = 0.001 |
196 parameters | Δρmax = 0.20 e Å−3 |
6 restraints | Δρmin = −0.22 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.0000 | 0.61843 (5) | 0.2500 | 0.04393 (18) | |
O1 | 0.12378 (17) | 0.69115 (13) | 0.22920 (5) | 0.0628 (4) | |
O2 | 0.64391 (16) | 0.46599 (18) | 0.34315 (6) | 0.0716 (4) | |
O3 | 0.34221 (18) | 0.18211 (14) | 0.42508 (5) | 0.0627 (4) | |
N1 | 0.53206 (17) | 0.30932 (14) | 0.39046 (5) | 0.0450 (3) | |
N2 | 0.8488 (2) | 0.07475 (18) | 0.44717 (6) | 0.0710 (5) | |
C1 | 0.10360 (18) | 0.50687 (15) | 0.29283 (5) | 0.0395 (3) | |
C2 | 0.27528 (19) | 0.51326 (16) | 0.30222 (5) | 0.0416 (3) | |
C3 | 0.34869 (18) | 0.42692 (15) | 0.33699 (5) | 0.0393 (3) | |
C4 | 0.25722 (19) | 0.33860 (15) | 0.36060 (5) | 0.0394 (3) | |
C5 | 0.0872 (2) | 0.33061 (18) | 0.35035 (6) | 0.0474 (4) | |
C6 | 0.00977 (19) | 0.41768 (19) | 0.31608 (6) | 0.0472 (4) | |
C7 | 0.5266 (2) | 0.40942 (18) | 0.35532 (6) | 0.0465 (4) | |
C8 | 0.3731 (2) | 0.26331 (16) | 0.39624 (6) | 0.0436 (4) | |
C9 | 0.6813 (2) | 0.26335 (17) | 0.41780 (5) | 0.0451 (4) | |
C10 | 0.7962 (2) | 0.35391 (19) | 0.43973 (7) | 0.0534 (4) | |
C11 | 0.9385 (3) | 0.3011 (2) | 0.46518 (7) | 0.0609 (5) | |
C12 | 0.9584 (3) | 0.1629 (2) | 0.46784 (7) | 0.0651 (5) | |
C13 | 0.7118 (3) | 0.12623 (19) | 0.42235 (7) | 0.0602 (5) | |
H2 | 0.338 (2) | 0.5717 (16) | 0.2850 (6) | 0.047 (5)* | |
H5 | 0.022 (2) | 0.2743 (17) | 0.3678 (6) | 0.054 (5)* | |
H6 | −0.1074 (12) | 0.419 (2) | 0.3095 (7) | 0.066 (6)* | |
H10 | 0.770 (2) | 0.4479 (11) | 0.4380 (7) | 0.061 (6)* | |
H11 | 1.022 (3) | 0.355 (2) | 0.4812 (9) | 0.073 (7)* | |
H12 | 1.054 (2) | 0.124 (2) | 0.4861 (8) | 0.081 (7)* | |
H13 | 0.632 (2) | 0.063 (2) | 0.4082 (7) | 0.071 (7)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0457 (3) | 0.0391 (3) | 0.0448 (3) | 0.000 | −0.0015 (2) | 0.000 |
O1 | 0.0626 (8) | 0.0558 (7) | 0.0661 (8) | −0.0151 (6) | −0.0044 (6) | 0.0205 (6) |
O2 | 0.0410 (6) | 0.0966 (11) | 0.0783 (9) | 0.0024 (7) | 0.0121 (6) | 0.0352 (8) |
O3 | 0.0712 (9) | 0.0542 (7) | 0.0600 (8) | −0.0115 (6) | −0.0004 (6) | 0.0201 (6) |
N1 | 0.0454 (7) | 0.0413 (7) | 0.0481 (7) | 0.0071 (5) | 0.0056 (6) | 0.0046 (5) |
N2 | 0.0838 (12) | 0.0578 (10) | 0.0654 (10) | 0.0311 (9) | −0.0113 (9) | −0.0040 (8) |
C1 | 0.0410 (7) | 0.0416 (7) | 0.0358 (7) | −0.0002 (6) | 0.0046 (6) | −0.0015 (6) |
C2 | 0.0400 (7) | 0.0430 (8) | 0.0426 (8) | −0.0015 (6) | 0.0087 (6) | 0.0045 (6) |
C3 | 0.0393 (7) | 0.0397 (7) | 0.0401 (7) | 0.0020 (6) | 0.0096 (6) | 0.0000 (6) |
C4 | 0.0454 (8) | 0.0367 (7) | 0.0367 (7) | −0.0018 (6) | 0.0079 (6) | −0.0017 (6) |
C5 | 0.0468 (8) | 0.0531 (9) | 0.0426 (8) | −0.0117 (7) | 0.0076 (6) | 0.0055 (7) |
C6 | 0.0380 (8) | 0.0588 (10) | 0.0445 (8) | −0.0068 (7) | 0.0050 (6) | 0.0015 (7) |
C7 | 0.0415 (8) | 0.0500 (9) | 0.0489 (9) | 0.0067 (6) | 0.0094 (6) | 0.0081 (7) |
C8 | 0.0517 (9) | 0.0355 (7) | 0.0428 (8) | −0.0014 (6) | 0.0043 (7) | 0.0001 (6) |
C9 | 0.0493 (8) | 0.0453 (8) | 0.0403 (8) | 0.0115 (7) | 0.0043 (6) | 0.0007 (6) |
C10 | 0.0581 (10) | 0.0476 (9) | 0.0537 (10) | 0.0022 (8) | 0.0045 (8) | 0.0044 (7) |
C11 | 0.0568 (10) | 0.0716 (12) | 0.0513 (10) | −0.0001 (9) | −0.0032 (8) | 0.0069 (9) |
C12 | 0.0656 (12) | 0.0771 (13) | 0.0493 (10) | 0.0227 (10) | −0.0041 (9) | 0.0052 (9) |
C13 | 0.0730 (12) | 0.0464 (10) | 0.0566 (10) | 0.0185 (9) | −0.0075 (9) | −0.0100 (8) |
Geometric parameters (Å, º) top
S1—O1 | 1.4360 (13) | C3—C4 | 1.385 (2) |
S1—O1i | 1.4360 (13) | C3—C7 | 1.486 (2) |
S1—C1i | 1.7746 (16) | C4—C5 | 1.382 (2) |
S1—C1 | 1.7746 (16) | C4—C8 | 1.491 (2) |
O2—C7 | 1.203 (2) | C5—C6 | 1.390 (2) |
O3—C8 | 1.203 (2) | C5—H5 | 0.957 (9) |
N1—C7 | 1.407 (2) | C6—H6 | 0.950 (10) |
N1—C8 | 1.408 (2) | C9—C13 | 1.380 (2) |
N1—C9 | 1.429 (2) | C9—C10 | 1.383 (3) |
N2—C12 | 1.328 (3) | C10—C11 | 1.387 (3) |
N2—C13 | 1.341 (2) | C10—H10 | 0.952 (10) |
C1—C2 | 1.393 (2) | C11—C12 | 1.375 (3) |
C1—C6 | 1.396 (2) | C11—H11 | 0.93 (3) |
C2—C3 | 1.383 (2) | C12—H12 | 0.954 (10) |
C2—H2 | 0.954 (9) | C13—H13 | 0.951 (10) |
O1—S1—O1i | 120.00 (12) | C5—C6—C1 | 120.06 (15) |
O1—S1—C1i | 108.62 (7) | C5—C6—H6 | 119.9 (14) |
O1i—S1—C1i | 107.55 (7) | C1—C6—H6 | 120.0 (14) |
O1—S1—C1 | 107.55 (7) | O2—C7—N1 | 125.90 (15) |
O1i—S1—C1 | 108.62 (7) | O2—C7—C3 | 128.60 (15) |
C1i—S1—C1 | 103.26 (10) | N1—C7—C3 | 105.49 (13) |
C7—N1—C8 | 111.87 (13) | O3—C8—N1 | 125.50 (16) |
C7—N1—C9 | 123.73 (14) | O3—C8—C4 | 128.98 (16) |
C8—N1—C9 | 124.38 (14) | N1—C8—C4 | 105.50 (13) |
C12—N2—C13 | 116.77 (17) | C13—C9—C10 | 119.29 (16) |
C2—C1—C6 | 122.80 (14) | C13—C9—N1 | 119.53 (16) |
C2—C1—S1 | 118.47 (11) | C10—C9—N1 | 121.19 (15) |
C6—C1—S1 | 118.73 (12) | C9—C10—C11 | 117.59 (17) |
C3—C2—C1 | 115.84 (13) | C9—C10—H10 | 118.4 (13) |
C3—C2—H2 | 122.4 (11) | C11—C10—H10 | 123.9 (13) |
C1—C2—H2 | 121.8 (11) | C12—C11—C10 | 119.1 (2) |
C2—C3—C4 | 122.03 (14) | C12—C11—H11 | 118.0 (15) |
C2—C3—C7 | 129.18 (14) | C10—C11—H11 | 122.8 (15) |
C4—C3—C7 | 108.79 (13) | N2—C12—C11 | 123.93 (18) |
C5—C4—C3 | 121.82 (14) | N2—C12—H12 | 115.6 (15) |
C5—C4—C8 | 129.88 (14) | C11—C12—H12 | 120.5 (15) |
C3—C4—C8 | 108.31 (13) | N2—C13—C9 | 123.30 (19) |
C4—C5—C6 | 117.43 (14) | N2—C13—H13 | 116.5 (15) |
C4—C5—H5 | 122.6 (12) | C9—C13—H13 | 120.2 (15) |
C6—C5—H5 | 119.8 (12) | ||
O1—S1—C1—C2 | 4.93 (15) | C4—C3—C7—O2 | 178.58 (19) |
O1i—S1—C1—C2 | −126.36 (13) | C2—C3—C7—N1 | 179.70 (15) |
C1i—S1—C1—C2 | 119.68 (14) | C4—C3—C7—N1 | −0.66 (18) |
O1—S1—C1—C6 | −175.84 (13) | C7—N1—C8—O3 | −176.93 (17) |
O1i—S1—C1—C6 | 52.88 (15) | C9—N1—C8—O3 | 1.3 (3) |
C1i—S1—C1—C6 | −61.09 (12) | C7—N1—C8—C4 | 1.62 (17) |
C6—C1—C2—C3 | −1.2 (2) | C9—N1—C8—C4 | 179.89 (14) |
S1—C1—C2—C3 | 178.01 (11) | C5—C4—C8—O3 | −2.9 (3) |
C1—C2—C3—C4 | 0.7 (2) | C3—C4—C8—O3 | 176.48 (17) |
C1—C2—C3—C7 | −179.72 (15) | C5—C4—C8—N1 | 178.59 (16) |
C2—C3—C4—C5 | 0.8 (2) | C3—C4—C8—N1 | −2.01 (16) |
C7—C3—C4—C5 | −178.89 (15) | C7—N1—C9—C13 | −130.56 (19) |
C2—C3—C4—C8 | −178.68 (14) | C8—N1—C9—C13 | 51.4 (2) |
C7—C3—C4—C8 | 1.65 (17) | C7—N1—C9—C10 | 49.3 (2) |
C3—C4—C5—C6 | −1.7 (2) | C8—N1—C9—C10 | −128.79 (18) |
C8—C4—C5—C6 | 177.61 (16) | C13—C9—C10—C11 | 0.5 (3) |
C4—C5—C6—C1 | 1.2 (3) | N1—C9—C10—C11 | −179.34 (16) |
C2—C1—C6—C5 | 0.2 (3) | C9—C10—C11—C12 | −0.6 (3) |
S1—C1—C6—C5 | −178.96 (13) | C13—N2—C12—C11 | 0.2 (3) |
C8—N1—C7—O2 | −179.94 (18) | C10—C11—C12—N2 | 0.2 (3) |
C9—N1—C7—O2 | 1.8 (3) | C12—N2—C13—C9 | −0.2 (3) |
C8—N1—C7—C3 | −0.66 (18) | C10—C9—C13—N2 | −0.1 (3) |
C9—N1—C7—C3 | −178.95 (14) | N1—C9—C13—N2 | 179.75 (18) |
C2—C3—C7—O2 | −1.1 (3) |
Symmetry code: (i) −x, y, −z+1/2. |