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ISSN: 2056-9890

N-[3-(Benzene­sulfonamido)­prop­yl]benzene­sulfonamide

aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, and bDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
*Correspondence e-mail: iuklodhi@yahoo.com

(Received 18 May 2011; accepted 26 May 2011; online 18 June 2011)

In the title compound, C15H18N2O4S2, the dihedral angle between the aromatic rings is 71.8 (2)°. The conformation of the central N—C—C—C—N fragment is gauchegauche [torsion angles = 72.5 (5) and 65.7 (5)°]. Both N atoms adopt pyramidal geometries. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds, generating (001) sheets, and weak C—H⋯O inter­actions consolidate the packing.

Related literature

For a related structure, see: Linden & Bienz (1999[Linden, A. & Bienz, S. (1999). Acta Cryst. C55 IUC9900046.]).

[Scheme 1]

Experimental

Crystal data
  • C15H18N2O4S2

  • Mr = 354.43

  • Orthorhombic, P b c a

  • a = 9.2650 (13) Å

  • b = 16.402 (2) Å

  • c = 22.740 (3) Å

  • V = 3455.5 (8) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.33 mm−1

  • T = 296 K

  • 0.40 × 0.20 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 13896 measured reflections

  • 3393 independent reflections

  • 1607 reflections with I > 2σ(I)

  • Rint = 0.091

Refinement
  • R[F2 > 2σ(F2)] = 0.069

  • wR(F2) = 0.181

  • S = 1.03

  • 3393 reflections

  • 215 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O4i 0.82 (4) 2.15 (5) 2.954 (6) 164 (4)
N2—H2⋯O3ii 0.74 (4) 2.15 (4) 2.836 (4) 154 (5)
C9—H9B⋯O4iii 0.97 2.51 3.430 (5) 158
C13—H13⋯O1iv 0.93 2.42 3.276 (8) 153
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (iii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (iv) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The title compound, (I), complements N-{4-[(benzenesulfonyl)amino]butyl}benzenesulfonamide, C16H20N2O4S2 (Linden & Bienz, 1999), (II), with a propyl chain in (I) replacing the butyl chain in (II).

In (I) (Fig. 1), the dihedral angle between the aromatic rings is 71.8 (2)°. The conformation of the central N—C—C—C—N chain linking the two S atoms can be described as gauche–gauche in terms of the N1—C7—C8—C9 and C7—C8—C9—N2 torsion angles of 72.5 (5) and 65.7 (5)°, respectively. Both N atoms in (I) are clearly in pyramidal coordination geometries, implying that the lone pairs on the N atoms are not conjugated with their adjacent benzene sulfonyl groups. A similar situation was observed in (II).

In the crystal of (I), the molecules are linked by N—H···O hydrogen bonds (Table 1). Considered separately, the N1 bond leads to [010] C(8) chains and the N2 bond generates [100] C(4) chains. Both the acceptor O atoms are part of the same (atom S2) sulfonyl group: it is perhaps notable that these O atoms have significantly smaller Ueq values that the O atoms in the other (atom S1) sulfonyl group that do not accept a hydrogen bond. Overall, (001) sheets arise from the N—H···O hydrogen bonds in (I) and weak C—H···O links consolidate the packing.

The complete molecule of (II) is generated by inversion symmetry and therefore the conformation of the central alkyl chain is all-trans and the dihedral angle between the aromatic rings is constrained to be zero by symmetry.

Related literature top

For a related structure, see: Linden & Bienz (1999).

Experimental top

A mixture of 1,3-diaminoprpoane (0.0067 mol, 0.561 ml) and benzene sulfonyl chloride (0.0135 mol, 1.72 ml), was stirred in 15 ml of distilled water, while maintaining the pH of the reaction mixture at 9 using 3% sodium carbonate. The progress of the reaction was checked by TLC. On completion, the precipitate obtained was filtered, washed with water and finally dried. Colourless blocks of (I) were grown from methanol by slow evaporation.

Refinement top

The N-bound H atoms were located in difference maps and their positions were freely refined with the constraint Uiso(H) = 1.2Ueq(N). The C-bound H atoms were placed at idealised positions and refined as riding with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.
N-[3-(Benzenesulfonamido)propyl]benzenesulfonamide top
Crystal data top
C15H18N2O4S2F(000) = 1488
Mr = 354.43Dx = 1.363 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2014 reflections
a = 9.2650 (13) Åθ = 2.6–21.2°
b = 16.402 (2) ŵ = 0.33 mm1
c = 22.740 (3) ÅT = 296 K
V = 3455.5 (8) Å3Prism, colourless
Z = 80.40 × 0.20 × 0.20 mm
Data collection top
Bruker APEXII CCD
diffractometer
1607 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.091
Graphite monochromatorθmax = 26.0°, θmin = 2.5°
ω scansh = 511
13896 measured reflectionsk = 1820
3393 independent reflectionsl = 2827
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069Hydrogen site location: difmap (N-H) and geom (C-H)
wR(F2) = 0.181H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0722P)2 + 0.3591P]
where P = (Fo2 + 2Fc2)/3
3393 reflections(Δ/σ)max < 0.001
215 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C15H18N2O4S2V = 3455.5 (8) Å3
Mr = 354.43Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 9.2650 (13) ŵ = 0.33 mm1
b = 16.402 (2) ÅT = 296 K
c = 22.740 (3) Å0.40 × 0.20 × 0.20 mm
Data collection top
Bruker APEXII CCD
diffractometer
1607 reflections with I > 2σ(I)
13896 measured reflectionsRint = 0.091
3393 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0690 restraints
wR(F2) = 0.181H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.23 e Å3
3393 reflectionsΔρmin = 0.35 e Å3
215 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1983 (7)0.4365 (4)0.3462 (2)0.0749 (16)
C20.0703 (9)0.4669 (4)0.3255 (3)0.102 (2)
H2A0.05800.52300.32190.123*
C30.0417 (9)0.4144 (6)0.3098 (3)0.124 (3)
H3A0.12760.43540.29500.148*
C40.0255 (10)0.3346 (5)0.3158 (3)0.118 (3)
H4A0.10040.29970.30530.141*
C50.0988 (12)0.3034 (4)0.3372 (3)0.118 (3)
H50.10900.24730.34140.142*
C60.2110 (8)0.3546 (4)0.3528 (3)0.102 (2)
H60.29580.33270.36790.123*
C70.1906 (5)0.5379 (3)0.4664 (2)0.0624 (13)
H7A0.11910.49480.46450.075*
H7B0.15390.58450.44470.075*
C80.2153 (5)0.5616 (3)0.5296 (2)0.0603 (13)
H8A0.12240.56660.54890.072*
H8B0.26770.51790.54890.072*
C90.2973 (4)0.6398 (2)0.5381 (2)0.0556 (12)
H9A0.31800.64760.57950.067*
H9B0.38830.63710.51710.067*
C100.3019 (4)0.8225 (2)0.5942 (2)0.0490 (11)
C110.4299 (5)0.7968 (3)0.6201 (2)0.0680 (14)
H110.50020.77050.59800.082*
C120.4507 (8)0.8108 (4)0.6785 (3)0.096 (2)
H120.53550.79300.69630.116*
C130.3495 (10)0.8504 (5)0.7115 (3)0.106 (2)
H130.36500.85890.75140.128*
C140.2258 (8)0.8775 (3)0.6857 (3)0.095 (2)
H140.15850.90610.70790.114*
C150.1992 (6)0.8627 (3)0.6261 (3)0.0738 (15)
H150.11360.87980.60870.089*
S10.33690 (18)0.50195 (11)0.36927 (6)0.0851 (5)
S20.27067 (10)0.79981 (7)0.52013 (5)0.0495 (4)
N10.3261 (4)0.5097 (3)0.43942 (19)0.0622 (12)
H10.349 (5)0.466 (3)0.455 (2)0.064 (17)*
N20.2115 (3)0.7085 (2)0.51605 (18)0.0547 (10)
H20.135 (5)0.708 (3)0.525 (2)0.066*
O10.3051 (5)0.5811 (3)0.34561 (18)0.1226 (17)
O20.4721 (5)0.4642 (3)0.35702 (17)0.1228 (17)
O30.4064 (3)0.8029 (2)0.49056 (13)0.0654 (9)
O40.1556 (3)0.85005 (18)0.49911 (14)0.0637 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.106 (5)0.064 (4)0.054 (3)0.007 (3)0.002 (3)0.011 (3)
C20.140 (6)0.064 (4)0.104 (5)0.017 (4)0.029 (5)0.018 (3)
C30.137 (7)0.110 (7)0.125 (6)0.012 (5)0.049 (5)0.002 (5)
C40.170 (8)0.086 (6)0.097 (5)0.031 (6)0.025 (5)0.008 (4)
C50.202 (9)0.059 (5)0.093 (5)0.010 (6)0.022 (6)0.010 (4)
C60.144 (6)0.072 (5)0.090 (4)0.001 (5)0.016 (4)0.009 (4)
C70.051 (3)0.048 (3)0.088 (4)0.005 (2)0.003 (3)0.006 (3)
C80.053 (3)0.045 (3)0.083 (4)0.003 (2)0.002 (3)0.005 (2)
C90.044 (2)0.046 (3)0.077 (3)0.005 (2)0.013 (2)0.000 (2)
C100.045 (3)0.033 (2)0.068 (3)0.0005 (19)0.009 (2)0.000 (2)
C110.055 (3)0.067 (4)0.082 (4)0.005 (3)0.008 (3)0.011 (3)
C120.103 (5)0.098 (5)0.088 (5)0.012 (4)0.021 (4)0.020 (4)
C130.144 (7)0.089 (5)0.086 (5)0.015 (5)0.001 (5)0.005 (4)
C140.122 (6)0.063 (4)0.099 (5)0.010 (4)0.045 (5)0.017 (4)
C150.069 (4)0.055 (4)0.098 (4)0.001 (3)0.017 (3)0.006 (3)
S10.0949 (12)0.0843 (12)0.0762 (10)0.0253 (10)0.0100 (8)0.0154 (9)
S20.0281 (5)0.0490 (7)0.0714 (8)0.0022 (5)0.0015 (5)0.0115 (6)
N10.062 (3)0.049 (3)0.075 (3)0.004 (2)0.002 (2)0.005 (2)
N20.0289 (17)0.048 (2)0.087 (3)0.0049 (18)0.001 (2)0.007 (2)
O10.176 (5)0.095 (3)0.098 (3)0.049 (3)0.024 (3)0.050 (3)
O20.091 (3)0.169 (5)0.108 (3)0.015 (3)0.045 (3)0.021 (3)
O30.0318 (15)0.090 (2)0.075 (2)0.0012 (16)0.0080 (15)0.0128 (18)
O40.0395 (16)0.057 (2)0.095 (2)0.0091 (15)0.0078 (16)0.0255 (17)
Geometric parameters (Å, º) top
C1—C61.357 (7)C9—H9B0.9700
C1—C21.370 (8)C10—C151.368 (6)
C1—S11.754 (6)C10—C111.390 (6)
C2—C31.395 (9)C10—S21.748 (5)
C2—H2A0.9300C11—C121.362 (7)
C3—C41.325 (9)C11—H110.9300
C3—H3A0.9300C12—C131.365 (9)
C4—C51.351 (9)C12—H120.9300
C4—H4A0.9300C13—C141.362 (9)
C5—C61.382 (9)C13—H130.9300
C5—H50.9300C14—C151.398 (7)
C6—H60.9300C14—H140.9300
C7—N11.471 (6)C15—H150.9300
C7—C81.506 (6)S1—O21.424 (4)
C7—H7A0.9700S1—O11.435 (4)
C7—H7B0.9700S1—N11.603 (4)
C8—C91.503 (6)S2—O31.427 (3)
C8—H8A0.9700S2—O41.430 (3)
C8—H8B0.9700S2—N21.597 (4)
C9—N21.468 (5)N1—H10.82 (4)
C9—H9A0.9700N2—H20.74 (4)
C6—C1—C2118.3 (6)C15—C10—C11120.9 (5)
C6—C1—S1120.7 (5)C15—C10—S2120.0 (4)
C2—C1—S1120.9 (5)C11—C10—S2119.1 (4)
C1—C2—C3120.4 (6)C12—C11—C10118.9 (5)
C1—C2—H2A119.8C12—C11—H11120.5
C3—C2—H2A119.8C10—C11—H11120.5
C4—C3—C2120.0 (8)C11—C12—C13121.2 (6)
C4—C3—H3A120.0C11—C12—H12119.4
C2—C3—H3A120.0C13—C12—H12119.4
C3—C4—C5120.5 (8)C14—C13—C12119.8 (6)
C3—C4—H4A119.7C14—C13—H13120.1
C5—C4—H4A119.7C12—C13—H13120.1
C4—C5—C6120.3 (7)C13—C14—C15120.6 (6)
C4—C5—H5119.9C13—C14—H14119.7
C6—C5—H5119.9C15—C14—H14119.7
C1—C6—C5120.5 (7)C10—C15—C14118.4 (5)
C1—C6—H6119.7C10—C15—H15120.8
C5—C6—H6119.7C14—C15—H15120.8
N1—C7—C8110.4 (4)O2—S1—O1120.0 (3)
N1—C7—H7A109.6O2—S1—N1106.5 (3)
C8—C7—H7A109.6O1—S1—N1106.8 (3)
N1—C7—H7B109.6O2—S1—C1108.6 (3)
C8—C7—H7B109.6O1—S1—C1106.9 (3)
H7A—C7—H7B108.1N1—S1—C1107.4 (2)
C9—C8—C7114.8 (4)O3—S2—O4118.66 (18)
C9—C8—H8A108.6O3—S2—N2107.9 (2)
C7—C8—H8A108.6O4—S2—N2105.36 (18)
C9—C8—H8B108.6O3—S2—C10107.48 (19)
C7—C8—H8B108.6O4—S2—C10108.8 (2)
H8A—C8—H8B107.6N2—S2—C10108.2 (2)
N2—C9—C8109.8 (3)C7—N1—S1119.5 (4)
N2—C9—H9A109.7C7—N1—H1108 (3)
C8—C9—H9A109.7S1—N1—H1110 (3)
N2—C9—H9B109.7C9—N2—S2121.0 (3)
C8—C9—H9B109.7C9—N2—H2115 (4)
H9A—C9—H9B108.2S2—N2—H2109 (4)
C6—C1—C2—C32.1 (9)C2—C1—S1—O2147.7 (5)
S1—C1—C2—C3177.1 (5)C6—C1—S1—O1168.2 (5)
C1—C2—C3—C41.2 (11)C2—C1—S1—O116.9 (6)
C2—C3—C4—C50.0 (12)C6—C1—S1—N177.5 (5)
C3—C4—C5—C60.2 (12)C2—C1—S1—N197.4 (5)
C2—C1—C6—C51.9 (9)C15—C10—S2—O3147.5 (4)
S1—C1—C6—C5176.9 (5)C11—C10—S2—O334.5 (4)
C4—C5—C6—C10.8 (10)C15—C10—S2—O417.8 (4)
N1—C7—C8—C972.5 (5)C11—C10—S2—O4164.2 (3)
C7—C8—C9—N265.7 (5)C15—C10—S2—N296.2 (4)
C15—C10—C11—C121.4 (7)C11—C10—S2—N281.8 (4)
S2—C10—C11—C12176.6 (4)C8—C7—N1—S1165.2 (3)
C10—C11—C12—C131.0 (9)O2—S1—N1—C7173.0 (4)
C11—C12—C13—C140.8 (10)O1—S1—N1—C757.7 (4)
C12—C13—C14—C152.2 (10)C1—S1—N1—C756.7 (4)
C11—C10—C15—C140.0 (7)C8—C9—N2—S2179.2 (3)
S2—C10—C15—C14178.0 (4)O3—S2—N2—C956.7 (4)
C13—C14—C15—C101.8 (8)O4—S2—N2—C9175.6 (3)
C6—C1—S1—O237.4 (5)C10—S2—N2—C959.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.82 (4)2.15 (5)2.954 (6)164 (4)
N2—H2···O3ii0.74 (4)2.15 (4)2.836 (4)154 (5)
C9—H9B···O4iii0.972.513.430 (5)158
C13—H13···O1iv0.932.423.276 (8)153
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x1/2, y+3/2, z+1; (iii) x+1/2, y+3/2, z+1; (iv) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H18N2O4S2
Mr354.43
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)296
a, b, c (Å)9.2650 (13), 16.402 (2), 22.740 (3)
V3)3455.5 (8)
Z8
Radiation typeMo Kα
µ (mm1)0.33
Crystal size (mm)0.40 × 0.20 × 0.20
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
13896, 3393, 1607
Rint0.091
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.069, 0.181, 1.03
No. of reflections3393
No. of parameters215
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.23, 0.35

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.82 (4)2.15 (5)2.954 (6)164 (4)
N2—H2···O3ii0.74 (4)2.15 (4)2.836 (4)154 (5)
C9—H9B···O4iii0.972.513.430 (5)158
C13—H13···O1iv0.932.423.276 (8)153
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x1/2, y+3/2, z+1; (iii) x+1/2, y+3/2, z+1; (iv) x, y+3/2, z+1/2.
 

Acknowledgements

IUK thanks the Higher Education Commission of Pakistan for financial support under the project to strengthen the Materials Chemistry Laboratory at GCUL.

References

First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationLinden, A. & Bienz, S. (1999). Acta Cryst. C55 IUC9900046.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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