3-(1H-Indol-3-yl)-2-(2-nitro-benzene-sulfonamido)-propanoic acid including an unknown solvate.

In the title compound, C(17)H(15)N(3)O(6)S, which crystallized with highly disordered methanol and/or water solvent mol-ecules, the dihedral angle between the the indole and benzene ring systems is 5.3 (2)°, which allows for the formation of intra-molecular π-π stacking inter-actions [centroid-centroid separations = 3.641 (3) and 3.694 (3) Å] and an approximate overall U-shape for the mol-ecule. In the crystal, dimers linked by pairs of N(s)-H⋯O(c) (s = sulfonamide and c = carboxyl-ate) hydrogen bonds generate R(2) (2)(10) loops, whereas N(i)-H⋯π (i = indole) inter-actions lead to chains propagating in [100] or [010]. Together, these lead to a three-dimensional network in which the solvent voids are present as inter-secting (two-dimensional) systems of [100] and [010] channels. The title compound was found to contain a heavily disordered solvent mol-ecule, which could be methanol or water or a mixture of the two. Due to its uncertain nature and the unresolvable disorder, the data were processed with the SQUEEZE option in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148-155], which revealed 877.8 Å(3) of solvent-accessible volume per unit cell and 126 electron-units of scattering density or 109.7 Å(3) (16 electron units) per organic mol-ecule.. This was not included in the calculations of overall formula weight, density and absorption coefficient.

Related literature

For related structures and background references to the biological activity of sulfonamides, see: Khan et al. (2011a ▶,b ▶). For further synthetic details, see: Deng & Mani (2006 ▶).

Experimental

Crystal data

C17H15N3O6S

M = 389.38

Tetragonal,

a = 9.6818 (5) Å

c = 44.017 (3) Å

V = 4126.0 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.19 mm−1

T = 296 K

0.30 × 0.25 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

4042 measured reflections

4042 independent reflections

3492 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.168

S = 1.07

4042 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1581 Friedel pairs

Flack parameter: 0.03 (15)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812023446/sj5218sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023446/sj5218Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023446/sj5218Isup3.cml

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

C17H15N3O6S	Dx = 1.254 Mg m−3
Mr = 389.38	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212	Cell parameters from 9980 reflections
Hall symbol: P 4abw 2nw	θ = 2.8–26.9°
a = 9.6818 (5) Å	µ = 0.19 mm−1
c = 44.017 (3) Å	T = 296 K
V = 4126.0 (4) Å3	Block, yellow
Z = 8	0.30 × 0.25 × 0.10 mm
F(000) = 1616

Bruker Kappa APEXII CCD diffractometer	3492 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 26.0°, θmin = 2.5°
ω scans	h = −7→8
4042 measured reflections	k = 0→11
4042 independent reflections	l = 0→54

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.067	w = 1/[σ2(Fo2) + (0.0679P)2 + 3.5726P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.168	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.21 e Å−3
4042 reflections	Δρmin = −0.24 e Å−3
245 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0083 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1581 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.03 (15)

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
C1	0.5558 (4)	0.6025 (4)	0.39025 (8)	0.0488 (8)
C2	0.6443 (5)	0.5208 (5)	0.37363 (10)	0.0583 (10)
H2A	0.7108	0.4675	0.3834	0.070*
C3	0.6335 (6)	0.5186 (6)	0.34215 (11)	0.0780 (15)
H3A	0.6925	0.4627	0.3309	0.094*
C4	0.5350 (7)	0.5994 (6)	0.32731 (10)	0.0792 (15)
H4	0.5306	0.5977	0.3062	0.095*
C5	0.4460 (6)	0.6799 (6)	0.34293 (11)	0.0763 (14)
H5	0.3799	0.7328	0.3329	0.092*
C6	0.4564 (5)	0.6813 (4)	0.37487 (9)	0.0558 (10)
C7	0.4312 (5)	0.7179 (5)	0.42414 (10)	0.0641 (11)
H7	0.3953	0.7511	0.4423	0.077*
C8	0.5374 (4)	0.6301 (4)	0.42204 (8)	0.0505 (9)
C9	0.6174 (4)	0.5663 (4)	0.44725 (9)	0.0554 (10)
H9A	0.6013	0.6180	0.4658	0.067*
H9B	0.7152	0.5717	0.4426	0.067*
C10	0.5775 (4)	0.4149 (4)	0.45240 (8)	0.0500 (9)
H10	0.5916	0.3639	0.4334	0.060*
C11	0.6702 (4)	0.3540 (4)	0.47649 (8)	0.0481 (9)
C12	0.2877 (4)	0.3494 (4)	0.40872 (8)	0.0467 (8)
C13	0.3606 (5)	0.2926 (5)	0.38483 (9)	0.0612 (11)
H13	0.4322	0.2310	0.3887	0.073*
C14	0.3275 (6)	0.3271 (6)	0.35519 (9)	0.0734 (14)
H14	0.3782	0.2905	0.3391	0.088*
C15	0.2204 (7)	0.4150 (6)	0.34959 (10)	0.0777 (14)
H15	0.1990	0.4378	0.3296	0.093*
C16	0.1439 (5)	0.4701 (6)	0.37262 (11)	0.0718 (13)
H16	0.0696	0.5281	0.3686	0.086*
C17	0.1800 (4)	0.4373 (4)	0.40226 (9)	0.0552 (10)
S1	0.33465 (11)	0.29054 (11)	0.44601 (2)	0.0528 (3)
N1	0.3822 (4)	0.7526 (4)	0.39580 (9)	0.0713 (11)
H1	0.3162	0.8094	0.3920	0.086*
N2	0.4319 (3)	0.4032 (3)	0.46119 (6)	0.0484 (7)
H2	0.3988	0.4579	0.4747	0.058*
N3	0.0981 (4)	0.5018 (4)	0.42620 (10)	0.0664 (10)
O1	0.6449 (3)	0.3541 (4)	0.50311 (6)	0.0781 (10)
O2	0.7836 (3)	0.3064 (4)	0.46516 (6)	0.0853 (12)
H3	0.8481	0.2766	0.4797	0.102*
O3	0.4148 (3)	0.1700 (3)	0.44107 (7)	0.0718 (9)
O4	0.2103 (3)	0.2828 (4)	0.46327 (7)	0.0755 (10)
O5	0.1554 (4)	0.5580 (5)	0.44684 (9)	0.0921 (12)
O6	−0.0272 (4)	0.4964 (5)	0.42333 (11)	0.0987 (13)

	U11	U22	U33	U12	U13	U23
C1	0.055 (2)	0.044 (2)	0.0473 (18)	−0.0035 (17)	0.0050 (17)	0.0033 (16)
C2	0.059 (3)	0.053 (2)	0.062 (2)	−0.005 (2)	0.006 (2)	−0.0003 (19)
C3	0.096 (4)	0.071 (3)	0.068 (3)	−0.006 (3)	0.028 (3)	−0.012 (2)
C4	0.112 (5)	0.075 (3)	0.050 (2)	−0.024 (3)	−0.001 (3)	0.007 (2)
C5	0.087 (4)	0.078 (3)	0.064 (3)	−0.005 (3)	−0.012 (3)	0.021 (3)
C6	0.062 (3)	0.049 (2)	0.057 (2)	−0.004 (2)	−0.0034 (18)	0.0095 (18)
C7	0.068 (3)	0.068 (3)	0.056 (2)	0.005 (2)	0.011 (2)	0.004 (2)
C8	0.057 (2)	0.044 (2)	0.0509 (19)	−0.0017 (17)	0.0004 (17)	0.0059 (16)
C9	0.057 (2)	0.056 (2)	0.053 (2)	−0.0113 (18)	−0.0096 (18)	0.0039 (18)
C10	0.054 (2)	0.062 (2)	0.0342 (15)	0.0002 (19)	−0.0001 (15)	−0.0023 (15)
C11	0.049 (2)	0.055 (2)	0.0394 (16)	0.0018 (17)	0.0053 (15)	0.0022 (15)
C12	0.046 (2)	0.049 (2)	0.0459 (17)	−0.0078 (17)	−0.0033 (16)	−0.0022 (15)
C13	0.060 (3)	0.066 (3)	0.057 (2)	−0.007 (2)	0.0011 (19)	−0.013 (2)
C14	0.085 (3)	0.086 (3)	0.050 (2)	−0.031 (3)	0.006 (2)	−0.010 (2)
C15	0.099 (4)	0.082 (4)	0.051 (2)	−0.028 (3)	−0.015 (3)	0.004 (2)
C16	0.058 (3)	0.081 (3)	0.077 (3)	−0.007 (2)	−0.019 (2)	0.013 (2)
C17	0.044 (2)	0.060 (2)	0.062 (2)	−0.0064 (19)	−0.0104 (18)	0.0037 (19)
S1	0.0515 (6)	0.0560 (6)	0.0508 (5)	−0.0032 (5)	−0.0041 (4)	0.0055 (4)
N1	0.070 (3)	0.064 (2)	0.080 (2)	0.0302 (19)	0.002 (2)	0.0077 (19)
N2	0.0449 (17)	0.060 (2)	0.0401 (14)	0.0036 (15)	0.0014 (13)	−0.0026 (14)
N3	0.050 (2)	0.069 (3)	0.081 (2)	0.0070 (18)	0.0047 (19)	0.014 (2)
O1	0.068 (2)	0.128 (3)	0.0381 (13)	0.030 (2)	0.0032 (13)	0.0059 (16)
O2	0.0609 (19)	0.147 (4)	0.0478 (14)	0.039 (2)	0.0108 (14)	0.0140 (19)
O3	0.076 (2)	0.0584 (18)	0.081 (2)	0.0064 (17)	−0.0180 (17)	−0.0001 (16)
O4	0.0590 (18)	0.102 (3)	0.0655 (17)	−0.0225 (18)	0.0054 (15)	0.0188 (18)
O5	0.075 (2)	0.118 (3)	0.082 (2)	0.013 (2)	0.010 (2)	−0.031 (2)
O6	0.046 (2)	0.115 (3)	0.135 (3)	0.010 (2)	0.000 (2)	0.015 (3)

C1—C2	1.377 (6)	C11—O1	1.197 (4)
C1—C6	1.402 (6)	C11—O2	1.291 (5)
C1—C8	1.436 (5)	C12—C17	1.375 (5)
C2—C3	1.390 (7)	C12—C13	1.381 (6)
C2—H2A	0.9300	C12—S1	1.796 (4)
C3—C4	1.396 (8)	C13—C14	1.384 (6)
C3—H3A	0.9300	C13—H13	0.9300
C4—C5	1.350 (8)	C14—C15	1.363 (8)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.410 (6)	C15—C16	1.364 (8)
C5—H5	0.9300	C15—H15	0.9300
C6—N1	1.356 (6)	C16—C17	1.387 (6)
C7—C8	1.337 (6)	C16—H16	0.9300
C7—N1	1.376 (6)	C17—N3	1.459 (6)
C7—H7	0.9300	S1—O3	1.418 (3)
C8—C9	1.488 (5)	S1—O4	1.426 (3)
C9—C10	1.533 (6)	S1—N2	1.588 (3)
C9—H9A	0.9700	N1—H1	0.8600
C9—H9B	0.9700	N2—H2	0.8600
C10—N2	1.466 (5)	N3—O5	1.195 (5)
C10—C11	1.509 (5)	N3—O6	1.221 (5)
C10—H10	0.9800	O2—H3	0.9400
C2—C1—C6	118.9 (4)	O1—C11—C10	124.5 (4)
C2—C1—C8	134.6 (4)	O2—C11—C10	111.9 (3)
C6—C1—C8	106.5 (4)	C17—C12—C13	118.5 (4)
C1—C2—C3	119.5 (5)	C17—C12—S1	125.2 (3)
C1—C2—H2A	120.3	C13—C12—S1	116.1 (3)
C3—C2—H2A	120.3	C12—C13—C14	120.2 (5)
C2—C3—C4	120.6 (5)	C12—C13—H13	119.9
C2—C3—H3A	119.7	C14—C13—H13	119.9
C4—C3—H3A	119.7	C15—C14—C13	119.8 (5)
C5—C4—C3	121.5 (4)	C15—C14—H14	120.1
C5—C4—H4	119.3	C13—C14—H14	120.1
C3—C4—H4	119.3	C14—C15—C16	121.5 (4)
C4—C5—C6	117.9 (5)	C14—C15—H15	119.2
C4—C5—H5	121.1	C16—C15—H15	119.2
C6—C5—H5	121.1	C15—C16—C17	118.2 (5)
N1—C6—C1	108.2 (3)	C15—C16—H16	120.9
N1—C6—C5	130.1 (4)	C17—C16—H16	120.9
C1—C6—C5	121.7 (4)	C12—C17—C16	121.8 (4)
C8—C7—N1	110.9 (4)	C12—C17—N3	121.8 (4)
C8—C7—H7	124.5	C16—C17—N3	116.4 (4)
N1—C7—H7	124.5	O3—S1—O4	120.0 (2)
C7—C8—C1	106.3 (4)	O3—S1—N2	107.77 (18)
C7—C8—C9	127.8 (4)	O4—S1—N2	108.22 (19)
C1—C8—C9	125.8 (4)	O3—S1—C12	105.04 (19)
C8—C9—C10	112.1 (3)	O4—S1—C12	106.84 (19)
C8—C9—H9A	109.2	N2—S1—C12	108.47 (17)
C10—C9—H9A	109.2	C6—N1—C7	108.0 (4)
C8—C9—H9B	109.2	C6—N1—H1	126.0
C10—C9—H9B	109.2	C7—N1—H1	126.0
H9A—C9—H9B	107.9	C10—N2—S1	120.8 (3)
N2—C10—C11	110.9 (3)	C10—N2—H2	119.6
N2—C10—C9	110.8 (3)	S1—N2—H2	119.6
C11—C10—C9	109.1 (3)	O5—N3—O6	124.0 (5)
N2—C10—H10	108.7	O5—N3—C17	119.4 (4)
C11—C10—H10	108.7	O6—N3—C17	116.6 (5)
C9—C10—H10	108.7	C11—O2—H3	114.3
O1—C11—O2	123.5 (4)
C6—C1—C2—C3	0.2 (6)	C12—C13—C14—C15	−1.5 (7)
C8—C1—C2—C3	−179.9 (5)	C13—C14—C15—C16	−0.2 (8)
C1—C2—C3—C4	0.7 (7)	C14—C15—C16—C17	1.6 (8)
C2—C3—C4—C5	−1.2 (8)	C13—C12—C17—C16	−0.2 (6)
C3—C4—C5—C6	0.7 (8)	S1—C12—C17—C16	−175.2 (4)
C2—C1—C6—N1	−179.9 (4)	C13—C12—C17—N3	−179.9 (4)
C8—C1—C6—N1	0.1 (5)	S1—C12—C17—N3	5.2 (6)
C2—C1—C6—C5	−0.7 (6)	C15—C16—C17—C12	−1.4 (7)
C8—C1—C6—C5	179.4 (4)	C15—C16—C17—N3	178.2 (4)
C4—C5—C6—N1	179.3 (5)	C17—C12—S1—O3	160.3 (4)
C4—C5—C6—C1	0.2 (7)	C13—C12—S1—O3	−14.8 (4)
N1—C7—C8—C1	−1.9 (5)	C17—C12—S1—O4	31.7 (4)
N1—C7—C8—C9	−178.9 (4)	C13—C12—S1—O4	−143.3 (3)
C2—C1—C8—C7	−178.9 (5)	C17—C12—S1—N2	−84.7 (4)
C6—C1—C8—C7	1.1 (5)	C13—C12—S1—N2	100.2 (3)
C2—C1—C8—C9	−1.7 (7)	C1—C6—N1—C7	−1.2 (5)
C6—C1—C8—C9	178.2 (4)	C5—C6—N1—C7	179.6 (5)
C7—C8—C9—C10	103.7 (5)	C8—C7—N1—C6	2.0 (6)
C1—C8—C9—C10	−72.8 (5)	C11—C10—N2—S1	−104.3 (3)
C8—C9—C10—N2	−62.1 (4)	C9—C10—N2—S1	134.4 (3)
C8—C9—C10—C11	175.6 (3)	O3—S1—N2—C10	36.3 (3)
N2—C10—C11—O1	−31.5 (6)	O4—S1—N2—C10	167.5 (3)
C9—C10—C11—O1	90.8 (5)	C12—S1—N2—C10	−76.9 (3)
N2—C10—C11—O2	151.1 (4)	C12—C17—N3—O5	48.9 (6)
C9—C10—C11—O2	−86.6 (4)	C16—C17—N3—O5	−130.7 (5)
C17—C12—C13—C14	1.7 (6)	C12—C17—N3—O6	−132.4 (5)
S1—C12—C13—C14	177.1 (3)	C16—C17—N3—O6	48.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cg1i	0.86	2.77	3.565 (4)	155
N2—H2···O1ii	0.86	2.10	2.918 (4)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cg1i	0.86	2.77	3.565 (4)	155
N2—H2⋯O1ii	0.86	2.10	2.918 (4)	158

Symmetry codes: (i) ; (ii) .