4-[(1,3-Dioxoisoindolin-2-yl)meth-yl]benzene-sulfonamide.

The title compound, C15H12N2O4S, is V-shaped with the isoindoline ring system (r.m.s. deviation = 0.006 Å) inclined to the benzene ring by 84.27 (13)°. In the crystal, inversion dimers are formed via pairwise N-H⋯O hydrogen bonds. These dimers associate further into corrugated ribbons, via pairwise N-H⋯O and C-H⋯O hydrogen bonds, propagating along the a-axis direction and lying parallel to (001).

Related literature

For the biological activity of cyclic imides, see: Abdel-Aziz et al. (2011a ▶,b ▶); Abdel-Aziz (2007 ▶). For related crystal structures, see: Jiang et al. (2008 ▶); Li (2007 ▶); Warzecha et al. (2006 ▶). For the preparation of the title compound, see: Abdel-Aziz et al. (2011a ▶).

Experimental

Crystal data

C15H12N2O4S

M = 316.33

Monoclinic,

a = 4.9803 (1) Å

b = 26.5291 (7) Å

c = 10.2740 (3) Å

β = 90.804 (1)°

V = 1357.30 (6) Å3

Z = 4

Cu Kα radiation

μ = 2.33 mm−1

T = 100 K

0.27 × 0.07 × 0.02 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T min = 0.85, T max = 0.95

22413 measured reflections

2533 independent reflections

2277 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.097

S = 1.17

2533 reflections

207 parameters

60 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814002803/su2697sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002803/su2697Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002803/su2697Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H12N2O4S	F(000) = 656
Mr = 316.33	Dx = 1.548 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 4.9803 (1) Å	Cell parameters from 9982 reflections
b = 26.5291 (7) Å	θ = 3.3–69.7°
c = 10.2740 (3) Å	µ = 2.33 mm−1
β = 90.804 (1)°	T = 100 K
V = 1357.30 (6) Å3	Plate, colourless
Z = 4	0.27 × 0.07 × 0.02 mm

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2533 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2277 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.036
Detector resolution: 10.4167 pixels mm-1	θmax = 69.7°, θmin = 3.3°
ω scans	h = −6→5
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −32→32
Tmin = 0.85, Tmax = 0.95	l = −12→12
22413 measured reflections

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)] = 0.042	Hydrogen site location: mixed
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ2(Fo2) + (0.007P)2 + 2.7892P] where P = (Fo2 + 2Fc2)/3
2533 reflections	(Δ/σ)max < 0.001
207 parameters	Δρmax = 0.35 e Å−3
60 restraints	Δρmin = −0.48 e Å−3

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 Å) and included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms.

	x	y	z	Uiso*/Ueq
S1	0.34446 (12)	0.06815 (2)	0.37785 (6)	0.01772 (16)
O1	0.8787 (4)	0.29938 (7)	0.42647 (19)	0.0289 (5)
O2	0.2038 (4)	0.33953 (7)	0.70508 (18)	0.0270 (4)
O3	0.2231 (4)	0.03320 (7)	0.46699 (18)	0.0234 (4)
O4	0.1931 (4)	0.08113 (7)	0.26280 (17)	0.0228 (4)
N1	0.5522 (4)	0.30797 (8)	0.5821 (2)	0.0196 (5)
N2	0.6245 (5)	0.04320 (9)	0.3351 (2)	0.0213 (5)
H2A	0.699 (7)	0.0253 (13)	0.399 (3)	0.036 (9)*
H2B	0.734 (7)	0.0629 (13)	0.291 (3)	0.035 (9)*
C1	0.6940 (5)	0.32243 (10)	0.4720 (2)	0.0203 (5)
C2	0.5700 (5)	0.37076 (10)	0.4278 (2)	0.0195 (5)
C3	0.6315 (5)	0.40119 (10)	0.3228 (3)	0.0250 (6)
H3	0.7724	0.3928	0.2653	0.030*
C4	0.4774 (6)	0.44466 (10)	0.3052 (3)	0.0277 (6)
H4	0.5141	0.4665	0.2344	0.033*
C5	0.2713 (6)	0.45654 (10)	0.3897 (3)	0.0291 (6)
H5	0.1695	0.4864	0.3754	0.035*
C6	0.2107 (6)	0.42563 (10)	0.4950 (3)	0.0254 (6)
H6	0.0700	0.4337	0.5528	0.030*
C7	0.3644 (5)	0.38266 (9)	0.5114 (2)	0.0194 (5)
C8	0.3516 (5)	0.34265 (10)	0.6129 (2)	0.0195 (5)
C9	0.6122 (6)	0.26288 (10)	0.6576 (3)	0.0224 (6)
H9A	0.5115	0.2643	0.7400	0.027*
H9B	0.8060	0.2627	0.6803	0.027*
C10	0.5424 (5)	0.21422 (10)	0.5873 (2)	0.0200 (5)
C11	0.6909 (5)	0.17103 (10)	0.6137 (3)	0.0229 (6)
H11	0.8343	0.1723	0.6757	0.027*
C12	0.6324 (5)	0.12619 (10)	0.5508 (3)	0.0222 (6)
H12	0.7363	0.0969	0.5682	0.027*
C13	0.4197 (5)	0.12451 (9)	0.4619 (2)	0.0179 (5)
C14	0.2657 (5)	0.16688 (10)	0.4370 (3)	0.0212 (6)
H14	0.1191	0.1653	0.3769	0.025*
C15	0.3270 (5)	0.21161 (10)	0.5003 (3)	0.0229 (6)
H15	0.2208	0.2407	0.4841	0.027*

	U11	U22	U33	U12	U13	U23
S1	0.0184 (3)	0.0157 (3)	0.0191 (3)	−0.0011 (2)	−0.0001 (2)	0.0007 (2)
O1	0.0278 (11)	0.0321 (11)	0.0269 (10)	0.0094 (9)	0.0047 (8)	0.0021 (9)
O2	0.0296 (10)	0.0318 (11)	0.0197 (10)	0.0032 (8)	0.0056 (8)	0.0010 (8)
O3	0.0224 (10)	0.0206 (9)	0.0272 (10)	−0.0019 (7)	0.0032 (8)	0.0046 (8)
O4	0.0249 (10)	0.0214 (9)	0.0219 (9)	−0.0009 (7)	−0.0054 (7)	0.0002 (8)
N1	0.0235 (11)	0.0175 (11)	0.0177 (11)	0.0008 (9)	−0.0002 (9)	0.0004 (9)
N2	0.0221 (12)	0.0201 (12)	0.0218 (12)	−0.0002 (9)	0.0009 (10)	0.0003 (10)
C1	0.0221 (13)	0.0216 (13)	0.0171 (13)	0.0005 (10)	−0.0007 (10)	−0.0004 (10)
C2	0.0197 (13)	0.0201 (13)	0.0185 (13)	−0.0024 (10)	−0.0027 (10)	−0.0014 (10)
C3	0.0240 (14)	0.0282 (15)	0.0228 (14)	−0.0051 (11)	−0.0005 (11)	0.0029 (12)
C4	0.0346 (16)	0.0235 (14)	0.0249 (14)	−0.0083 (12)	−0.0063 (12)	0.0068 (12)
C5	0.0393 (17)	0.0173 (13)	0.0303 (15)	0.0034 (12)	−0.0098 (13)	0.0008 (12)
C6	0.0302 (15)	0.0219 (14)	0.0239 (14)	0.0061 (11)	−0.0043 (11)	−0.0042 (11)
C7	0.0223 (13)	0.0176 (12)	0.0183 (13)	−0.0009 (10)	−0.0044 (10)	−0.0008 (10)
C8	0.0220 (13)	0.0185 (13)	0.0178 (13)	−0.0001 (10)	−0.0026 (10)	−0.0043 (10)
C9	0.0288 (14)	0.0195 (13)	0.0189 (13)	0.0029 (11)	−0.0031 (11)	0.0021 (10)
C10	0.0243 (13)	0.0204 (13)	0.0155 (12)	0.0008 (10)	0.0022 (10)	0.0006 (10)
C11	0.0269 (14)	0.0226 (13)	0.0189 (13)	0.0022 (11)	−0.0058 (11)	0.0024 (11)
C12	0.0247 (14)	0.0186 (13)	0.0232 (14)	0.0037 (11)	−0.0035 (11)	0.0018 (11)
C13	0.0196 (13)	0.0176 (12)	0.0165 (12)	−0.0015 (10)	0.0029 (10)	0.0023 (10)
C14	0.0213 (13)	0.0223 (13)	0.0199 (13)	0.0006 (10)	−0.0027 (10)	0.0016 (11)
C15	0.0258 (14)	0.0192 (13)	0.0237 (14)	0.0044 (11)	−0.0028 (11)	0.0005 (11)

S1—O4	1.4350 (18)	C5—C6	1.394 (4)
S1—O3	1.4419 (18)	C5—H5	0.9500
S1—N2	1.610 (2)	C6—C7	1.382 (4)
S1—C13	1.764 (3)	C6—H6	0.9500
O1—C1	1.205 (3)	C7—C8	1.490 (4)
O2—C8	1.211 (3)	C9—C10	1.517 (4)
N1—C1	1.396 (3)	C9—H9A	0.9900
N1—C8	1.397 (3)	C9—H9B	0.9900
N1—C9	1.454 (3)	C10—C15	1.388 (4)
N2—H2A	0.89 (4)	C10—C11	1.389 (4)
N2—H2B	0.88 (3)	C11—C12	1.383 (4)
C1—C2	1.491 (4)	C11—H11	0.9500
C2—C7	1.382 (4)	C12—C13	1.390 (4)
C2—C3	1.385 (4)	C12—H12	0.9500
C3—C4	1.396 (4)	C13—C14	1.382 (4)
C3—H3	0.9500	C14—C15	1.386 (4)
C4—C5	1.390 (4)	C14—H14	0.9500
C4—H4	0.9500	C15—H15	0.9500
O4—S1—O3	117.22 (11)	C6—C7—C2	121.7 (2)
O4—S1—N2	108.72 (12)	C6—C7—C8	130.1 (2)
O3—S1—N2	106.35 (12)	C2—C7—C8	108.1 (2)
O4—S1—C13	107.77 (11)	O2—C8—N1	125.2 (2)
O3—S1—C13	108.78 (11)	O2—C8—C7	128.9 (2)
N2—S1—C13	107.65 (12)	N1—C8—C7	105.9 (2)
C1—N1—C8	111.9 (2)	N1—C9—C10	113.7 (2)
C1—N1—C9	123.8 (2)	N1—C9—H9A	108.8
C8—N1—C9	124.3 (2)	C10—C9—H9A	108.8
S1—N2—H2A	112 (2)	N1—C9—H9B	108.8
S1—N2—H2B	116 (2)	C10—C9—H9B	108.8
H2A—N2—H2B	116 (3)	H9A—C9—H9B	107.7
O1—C1—N1	125.0 (2)	C15—C10—C11	119.3 (2)
O1—C1—C2	129.3 (2)	C15—C10—C9	121.2 (2)
N1—C1—C2	105.7 (2)	C11—C10—C9	119.4 (2)
C7—C2—C3	121.7 (2)	C12—C11—C10	120.7 (2)
C7—C2—C1	108.3 (2)	C12—C11—H11	119.7
C3—C2—C1	130.0 (2)	C10—C11—H11	119.7
C2—C3—C4	117.1 (3)	C11—C12—C13	119.3 (2)
C2—C3—H3	121.5	C11—C12—H12	120.4
C4—C3—H3	121.5	C13—C12—H12	120.4
C5—C4—C3	121.1 (3)	C14—C13—C12	120.8 (2)
C5—C4—H4	119.5	C14—C13—S1	119.0 (2)
C3—C4—H4	119.5	C12—C13—S1	120.22 (19)
C4—C5—C6	121.4 (3)	C13—C14—C15	119.4 (2)
C4—C5—H5	119.3	C13—C14—H14	120.3
C6—C5—H5	119.3	C15—C14—H14	120.3
C7—C6—C5	117.0 (3)	C14—C15—C10	120.6 (2)
C7—C6—H6	121.5	C14—C15—H15	119.7
C5—C6—H6	121.5	C10—C15—H15	119.7
C8—N1—C1—O1	179.0 (3)	C2—C7—C8—O2	178.4 (3)
C9—N1—C1—O1	0.7 (4)	C6—C7—C8—N1	179.6 (3)
C8—N1—C1—C2	−0.5 (3)	C2—C7—C8—N1	−0.9 (3)
C9—N1—C1—C2	−178.9 (2)	C1—N1—C9—C10	−70.0 (3)
O1—C1—C2—C7	−179.6 (3)	C8—N1—C9—C10	111.9 (3)
N1—C1—C2—C7	−0.1 (3)	N1—C9—C10—C15	−32.3 (4)
O1—C1—C2—C3	1.0 (5)	N1—C9—C10—C11	149.9 (2)
N1—C1—C2—C3	−179.5 (3)	C15—C10—C11—C12	2.4 (4)
C7—C2—C3—C4	0.3 (4)	C9—C10—C11—C12	−179.8 (2)
C1—C2—C3—C4	179.7 (3)	C10—C11—C12—C13	−1.0 (4)
C2—C3—C4—C5	−0.1 (4)	C11—C12—C13—C14	−0.6 (4)
C3—C4—C5—C6	0.1 (4)	C11—C12—C13—S1	178.8 (2)
C4—C5—C6—C7	−0.1 (4)	O4—S1—C13—C14	20.6 (2)
C5—C6—C7—C2	0.2 (4)	O3—S1—C13—C14	−107.4 (2)
C5—C6—C7—C8	179.7 (3)	N2—S1—C13—C14	137.7 (2)
C3—C2—C7—C6	−0.3 (4)	O4—S1—C13—C12	−158.8 (2)
C1—C2—C7—C6	−179.8 (2)	O3—S1—C13—C12	73.2 (2)
C3—C2—C7—C8	−179.9 (2)	N2—S1—C13—C12	−41.7 (2)
C1—C2—C7—C8	0.6 (3)	C12—C13—C14—C15	0.8 (4)
C1—N1—C8—O2	−178.4 (2)	S1—C13—C14—C15	−178.5 (2)
C9—N1—C8—O2	−0.1 (4)	C13—C14—C15—C10	0.5 (4)
C1—N1—C8—C7	0.9 (3)	C11—C10—C15—C14	−2.1 (4)
C9—N1—C8—C7	179.2 (2)	C9—C10—C15—C14	−179.9 (2)
C6—C7—C8—O2	−1.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3i	0.89 (4)	2.11 (4)	2.963 (3)	162 (3)
N2—H2B···O4ii	0.88 (3)	2.36 (3)	3.105 (3)	142 (3)
C15—H15···O1iii	0.95	2.38	3.307 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3i	0.89 (4)	2.11 (4)	2.963 (3)	162 (3)
N2—H2B⋯O4ii	0.88 (3)	2.36 (3)	3.105 (3)	142 (3)
C15—H15⋯O1iii	0.95	2.38	3.307 (3)	166

Symmetry codes: (i) ; (ii) ; (iii) .