Bis(1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl) sulfone

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)°.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.125
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97

   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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

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

Crystal data

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) Å^3	0.36 × 0.28 × 0.21 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	All H-atom parameters refined
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0731P)^2 + 0.7633P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

S1—O1	1.4360 (13)	C3—C4	1.385 (2)
S1—O1^i	1.4360 (13)	C3—C7	1.486 (2)
S1—C1^i	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—O1^i	120.00 (12)	C5—C6—C1	120.06 (15)
O1—S1—C1^i	108.62 (7)	C5—C6—H6	119.9 (14)
O1^i—S1—C1^i	107.55 (7)	C1—C6—H6	120.0 (14)
O1—S1—C1	107.55 (7)	O2—C7—N1	125.90 (15)
O1^i—S1—C1	108.62 (7)	O2—C7—C3	128.60 (15)
C1^i—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)
O1^i—S1—C1—C2	−126.36 (13)	C2—C3—C7—N1	179.70 (15)
C1^i—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)
O1^i—S1—C1—C6	52.88 (15)	C9—N1—C8—O3	1.3 (3)
C1^i—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.