2-(1,3-Dioxoisoindolin-2-yl)ethyl 4-methyl-benzene-sulfonate.

In the title mol-ecule, C(17)H(15)NO(5)S, the dihedral angle between the essentially planar atoms of the tosyl moiety (the S atom and the seven tolyl C atoms) and the phthalimide moiety is 6.089 (3)°. The mol-ecule is folded about the ethyl-ene bridge, adopting a staggered conformation such that the benzene ring of the tosyl group and the five-membered ring of the phthalimide moiety have a face-to-face orientation with a centroid-to-centroid separation of 3.7454 (12) Å. The crystal structure is stabilized by weak inter-molecular π-π inter-actions between symmetry-related five-membered rings of the phthalimide groups, with a centroid-to-centroid distance of 3.3867 (11) Å. The compound is used for the attachment of a suitable chelate functionality for radiolabeling purposes.

Related literature

For general background, see: Eriksson et al. (2002 ▶); Arner & Eriksson (1995 ▶); Bello (1974 ▶); Wei et al. (2005 ▶); Welin et al. (2004 ▶). For reference bond distances, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H15NO5S

M = 345.36

Monoclinic,

a = 13.6817 (13) Å

b = 12.5642 (12) Å

c = 19.3194 (19) Å

β = 107.121 (2)°

V = 3173.8 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 90 (2) K

0.40 × 0.35 × 0.30 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Brucker, 2007 ▶) T min = 0.913, T max = 0.934

16184 measured reflections

3865 independent reflections

3773 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.122

S = 1.25

3865 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.41 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalMaker (Palmer, 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808037951/lh2734sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037951/lh2734Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H15NO5S	F000 = 1440
Mr = 345.36	Dx = 1.446 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C2yc	Cell parameters from 9534 reflections
a = 13.6817 (13) Å	θ = 2.2–28.3º
b = 12.5642 (12) Å	µ = 0.23 mm−1
c = 19.3194 (19) Å	T = 90 (2) K
β = 107.121 (2)º	Block, colourless
V = 3173.8 (5) Å3	0.40 × 0.35 × 0.30 mm
Z = 8

Bruker APEX CCD area-detector diffractometer	3865 independent reflections
Monochromator: graphite	3773 reflections with I > 2σ(I)
Detector resolution: 512 pixels mm-1	Rint = 0.020
T = 90(2) K	θmax = 28.1º
φ and ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS in SHELXL97; Sheldrick, 2008)	h = −18→18
Tmin = 0.913, Tmax = 0.934	k = −16→16
16184 measured reflections	l = −25→25

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)] = 0.052	H-atom parameters constrained
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0413P)2 + 6.2623P] where P = (Fo2 + 2Fc2)/3
S = 1.25	(Δ/σ)max = 0.001
3865 reflections	Δρmax = 0.48 e Å−3
218 parameters	Δρmin = −0.41 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
S1	0.24768 (3)	−0.05689 (4)	1.04905 (2)	0.01844 (13)
O1	0.27012 (11)	−0.16681 (11)	1.06516 (7)	0.0245 (3)
O2	0.26255 (12)	0.01842 (12)	1.10672 (7)	0.0269 (3)
O3	0.13136 (10)	−0.04377 (10)	1.00548 (7)	0.0195 (3)
O4	0.12124 (10)	−0.09920 (11)	0.78928 (7)	0.0214 (3)
O5	0.01573 (11)	0.16581 (11)	0.91348 (8)	0.0270 (3)
N1	0.05468 (11)	0.01454 (12)	0.85773 (8)	0.0179 (3)
C1	0.31279 (13)	−0.01266 (16)	0.98842 (10)	0.0193 (4)
C2	0.35460 (15)	−0.08611 (17)	0.95184 (11)	0.0243 (4)
H2	0.3486	−0.1603	0.9592	0.029*
C3	0.40571 (15)	−0.04904 (19)	0.90397 (11)	0.0287 (4)
H3	0.4350	−0.0988	0.8788	0.034*
C4	0.41464 (15)	0.0590 (2)	0.89231 (11)	0.0294 (5)
C5	0.46884 (19)	0.0980 (2)	0.83979 (13)	0.0425 (6)
H5A	0.5003	0.0376	0.8223	0.064*
H5B	0.5220	0.1491	0.8641	0.064*
H5C	0.4196	0.1328	0.7987	0.064*
C6	0.37176 (16)	0.13104 (18)	0.93012 (12)	0.0286 (4)
H6	0.3773	0.2052	0.9226	0.034*
C7	0.32129 (15)	0.09635 (16)	0.97844 (11)	0.0236 (4)
H7	0.2930	0.1460	1.0043	0.028*
C8	0.10819 (13)	−0.01011 (15)	0.80845 (9)	0.0169 (3)
C9	0.14229 (13)	0.09383 (15)	0.78653 (9)	0.0180 (3)
C10	0.19546 (15)	0.11612 (16)	0.73773 (10)	0.0218 (4)
H10	0.2158	0.0612	0.7111	0.026*
C11	0.21815 (16)	0.22272 (17)	0.72909 (11)	0.0270 (4)
H11	0.2547	0.2410	0.6959	0.032*
C12	0.18807 (17)	0.30273 (17)	0.76836 (11)	0.0276 (4)
H12	0.2055	0.3745	0.7620	0.033*
C13	0.13283 (15)	0.27955 (16)	0.81683 (10)	0.0232 (4)
H13	0.1115	0.3341	0.8432	0.028*
C14	0.11061 (13)	0.17402 (15)	0.82475 (9)	0.0182 (3)
C15	0.05463 (14)	0.12411 (14)	0.87179 (10)	0.0186 (4)
C16	0.00646 (14)	−0.06579 (15)	0.89112 (10)	0.0191 (4)
H16A	−0.0302	−0.1175	0.8538	0.023*
H16B	−0.0443	−0.0312	0.9112	0.023*
C17	0.08415 (14)	−0.12402 (14)	0.95089 (10)	0.0191 (4)
H17A	0.0505	−0.1797	0.9720	0.023*
H17B	0.1364	−0.1581	0.9320	0.023*

	U11	U22	U33	U12	U13	U23
S1	0.0222 (2)	0.0191 (2)	0.0151 (2)	−0.00308 (16)	0.00727 (16)	−0.00143 (16)
O1	0.0290 (7)	0.0227 (7)	0.0213 (7)	−0.0010 (6)	0.0067 (5)	0.0018 (5)
O2	0.0362 (8)	0.0282 (7)	0.0185 (6)	−0.0083 (6)	0.0113 (6)	−0.0065 (6)
O3	0.0209 (6)	0.0188 (6)	0.0209 (6)	−0.0023 (5)	0.0095 (5)	−0.0037 (5)
O4	0.0227 (7)	0.0198 (6)	0.0233 (6)	0.0022 (5)	0.0094 (5)	−0.0020 (5)
O5	0.0325 (8)	0.0237 (7)	0.0304 (7)	0.0001 (6)	0.0180 (6)	−0.0042 (6)
N1	0.0182 (7)	0.0181 (7)	0.0191 (7)	0.0008 (6)	0.0083 (6)	0.0005 (6)
C1	0.0169 (8)	0.0260 (9)	0.0151 (8)	−0.0037 (7)	0.0048 (6)	0.0001 (7)
C2	0.0222 (9)	0.0288 (10)	0.0223 (9)	−0.0010 (8)	0.0071 (7)	−0.0032 (8)
C3	0.0201 (9)	0.0450 (13)	0.0220 (9)	0.0003 (8)	0.0079 (7)	−0.0044 (9)
C4	0.0169 (9)	0.0493 (13)	0.0222 (9)	−0.0054 (8)	0.0061 (7)	0.0040 (9)
C5	0.0297 (11)	0.0686 (18)	0.0340 (12)	−0.0074 (11)	0.0167 (10)	0.0104 (12)
C6	0.0242 (10)	0.0316 (11)	0.0303 (10)	−0.0067 (8)	0.0085 (8)	0.0063 (8)
C7	0.0216 (9)	0.0248 (10)	0.0244 (9)	−0.0022 (7)	0.0069 (7)	−0.0003 (7)
C8	0.0137 (7)	0.0219 (9)	0.0150 (8)	0.0014 (6)	0.0042 (6)	0.0013 (6)
C9	0.0158 (8)	0.0202 (8)	0.0165 (8)	−0.0012 (6)	0.0026 (6)	−0.0005 (7)
C10	0.0225 (9)	0.0267 (10)	0.0171 (8)	−0.0034 (7)	0.0071 (7)	−0.0018 (7)
C11	0.0300 (10)	0.0321 (11)	0.0207 (9)	−0.0095 (8)	0.0105 (8)	−0.0003 (8)
C12	0.0351 (11)	0.0227 (9)	0.0248 (9)	−0.0103 (8)	0.0084 (8)	−0.0005 (8)
C13	0.0269 (10)	0.0211 (9)	0.0212 (9)	−0.0037 (7)	0.0066 (7)	−0.0033 (7)
C14	0.0167 (8)	0.0212 (9)	0.0163 (8)	−0.0017 (7)	0.0045 (6)	−0.0019 (7)
C15	0.0181 (8)	0.0178 (8)	0.0197 (8)	0.0001 (6)	0.0053 (7)	−0.0015 (7)
C16	0.0182 (8)	0.0196 (8)	0.0216 (9)	−0.0026 (7)	0.0092 (7)	0.0002 (7)
C17	0.0219 (8)	0.0169 (8)	0.0190 (8)	−0.0040 (7)	0.0068 (7)	−0.0025 (7)

S1—O1	1.4290 (15)	C6—C7	1.385 (3)
S1—O2	1.4299 (14)	C6—H6	0.9500
S1—O3	1.5747 (14)	C7—H7	0.9500
S1—C1	1.7574 (18)	C8—C9	1.489 (3)
O3—C17	1.465 (2)	C9—C10	1.379 (3)
O4—C8	1.209 (2)	C9—C14	1.392 (3)
O5—C15	1.208 (2)	C10—C11	1.396 (3)
N1—C8	1.396 (2)	C10—H10	0.9500
N1—C15	1.403 (2)	C11—C12	1.393 (3)
N1—C16	1.456 (2)	C11—H11	0.9500
C1—C2	1.384 (3)	C12—C13	1.396 (3)
C1—C7	1.393 (3)	C12—H12	0.9500
C2—C3	1.394 (3)	C13—C14	1.379 (3)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.387 (3)	C14—C15	1.488 (2)
C3—H3	0.9500	C16—C17	1.509 (3)
C4—C6	1.396 (3)	C16—H16A	0.9900
C4—C5	1.504 (3)	C16—H16B	0.9900
C5—H5A	0.9800	C17—H17A	0.9900
C5—H5B	0.9800	C17—H17B	0.9900
C5—H5C	0.9800
O1—S1—O2	119.84 (9)	O4—C8—C9	129.65 (17)
O1—S1—O3	109.64 (8)	N1—C8—C9	105.69 (15)
O2—S1—O3	103.69 (8)	C10—C9—C14	121.68 (18)
O1—S1—C1	109.41 (9)	C10—C9—C8	130.16 (17)
O2—S1—C1	109.05 (9)	C14—C9—C8	108.15 (16)
O3—S1—C1	103.97 (8)	C9—C10—C11	117.22 (18)
C17—O3—S1	118.36 (11)	C9—C10—H10	121.4
C8—N1—C15	112.32 (15)	C11—C10—H10	121.4
C8—N1—C16	123.05 (15)	C12—C11—C10	121.04 (18)
C15—N1—C16	124.62 (15)	C12—C11—H11	119.5
C2—C1—C7	121.40 (18)	C10—C11—H11	119.5
C2—C1—S1	119.74 (15)	C11—C12—C13	121.33 (19)
C7—C1—S1	118.85 (15)	C11—C12—H12	119.3
C1—C2—C3	118.6 (2)	C13—C12—H12	119.3
C1—C2—H2	120.7	C14—C13—C12	117.10 (18)
C3—C2—H2	120.7	C14—C13—H13	121.5
C4—C3—C2	121.3 (2)	C12—C13—H13	121.5
C4—C3—H3	119.3	C13—C14—C9	121.61 (17)
C2—C3—H3	119.3	C13—C14—C15	130.00 (17)
C3—C4—C6	118.61 (19)	C9—C14—C15	108.39 (16)
C3—C4—C5	120.9 (2)	O5—C15—N1	125.45 (17)
C6—C4—C5	120.5 (2)	O5—C15—C14	129.15 (17)
C4—C5—H5A	109.5	N1—C15—C14	105.40 (15)
C4—C5—H5B	109.5	N1—C16—C17	111.48 (15)
H5A—C5—H5B	109.5	N1—C16—H16A	109.3
C4—C5—H5C	109.5	C17—C16—H16A	109.3
H5A—C5—H5C	109.5	N1—C16—H16B	109.3
H5B—C5—H5C	109.5	C17—C16—H16B	109.3
C7—C6—C4	121.2 (2)	H16A—C16—H16B	108.0
C7—C6—H6	119.4	O3—C17—C16	106.23 (14)
C4—C6—H6	119.4	O3—C17—H17A	110.5
C6—C7—C1	118.77 (19)	C16—C17—H17A	110.5
C6—C7—H7	120.6	O3—C17—H17B	110.5
C1—C7—H7	120.6	C16—C17—H17B	110.5
O4—C8—N1	124.67 (17)	H17A—C17—H17B	108.7
O1—S1—O3—C17	−38.67 (14)	O4—C8—C9—C14	−178.67 (18)
O2—S1—O3—C17	−167.78 (12)	N1—C8—C9—C14	1.69 (19)
C1—S1—O3—C17	78.22 (14)	C14—C9—C10—C11	1.2 (3)
O1—S1—C1—C2	14.61 (18)	C8—C9—C10—C11	−179.09 (18)
O2—S1—C1—C2	147.43 (15)	C9—C10—C11—C12	0.0 (3)
O3—S1—C1—C2	−102.45 (16)	C10—C11—C12—C13	−1.0 (3)
O1—S1—C1—C7	−165.23 (15)	C11—C12—C13—C14	0.8 (3)
O2—S1—C1—C7	−32.41 (18)	C12—C13—C14—C9	0.4 (3)
O3—S1—C1—C7	77.71 (16)	C12—C13—C14—C15	179.45 (18)
C7—C1—C2—C3	−0.3 (3)	C10—C9—C14—C13	−1.4 (3)
S1—C1—C2—C3	179.90 (15)	C8—C9—C14—C13	178.79 (17)
C1—C2—C3—C4	−0.4 (3)	C10—C9—C14—C15	179.32 (16)
C2—C3—C4—C6	0.5 (3)	C8—C9—C14—C15	−0.45 (19)
C2—C3—C4—C5	−179.22 (19)	C8—N1—C15—O5	−178.31 (18)
C3—C4—C6—C7	0.1 (3)	C16—N1—C15—O5	0.7 (3)
C5—C4—C6—C7	179.75 (19)	C8—N1—C15—C14	2.1 (2)
C4—C6—C7—C1	−0.7 (3)	C16—N1—C15—C14	−178.90 (16)
C2—C1—C7—C6	0.8 (3)	C13—C14—C15—O5	0.3 (3)
S1—C1—C7—C6	−179.38 (15)	C9—C14—C15—O5	179.49 (19)
C15—N1—C8—O4	177.95 (17)	C13—C14—C15—N1	179.90 (19)
C16—N1—C8—O4	−1.1 (3)	C9—C14—C15—N1	−0.95 (19)
C15—N1—C8—C9	−2.38 (19)	C8—N1—C16—C17	76.8 (2)
C16—N1—C8—C9	178.62 (15)	C15—N1—C16—C17	−102.06 (19)
O4—C8—C9—C10	1.6 (3)	S1—O3—C17—C16	−146.02 (12)
N1—C8—C9—C10	−178.05 (18)	N1—C16—C17—O3	61.83 (18)