PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1499.
Published online 2008 July 16. doi:  10.1107/S1600536808021211
PMCID: PMC2962128

N,N′-Diisopropyl-3,6-dimethoxy­naphthalene-2,7-disulfonamide

Abstract

In the title compound, C18H26N2O6S2, all bond lengths and angles are normal. The crystal structure is stabilized by inter­molecular N—H(...)O hydrogen bonds.

Related literature

For the crystal structures of related compounds, see: Henschel et al. (1996 [triangle]). For details of the biological activities of fluorine-containing compounds, see: Kamoshita et al. (1987 [triangle]). For catalytic activity, see: Zhang et al. (2007 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1499-scheme1.jpg

Experimental

Crystal data

  • C18H26N2O6S2
  • M r = 430.53
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1499-efi1.jpg
  • a = 17.229 (3) Å
  • b = 7.2532 (15) Å
  • c = 18.035 (4) Å
  • β = 108.35 (3)°
  • V = 2139.2 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 173 (2) K
  • 0.50 × 0.38 × 0.22 mm

Data collection

  • Rigaku R-AXIS RAPID IP area-detector diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.871, T max = 0.940
  • 8740 measured reflections
  • 4889 independent reflections
  • 4227 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.117
  • S = 1.16
  • 4889 reflections
  • 253 parameters
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.49 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021211/hg2423sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021211/hg2423Isup2.hkl

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

supplementary crystallographic information

Comment

The sulfonamides form an important group in organic chemistry with many compounds containing sulfonamide groups possessing a broad spectrum of biological activities and can be widely used as herbicides (Kamoshita et al., 1987). In addition, some compounds containing sulfonimide groups can be used as catalysts (Zhang et al., 2007). Here, we report the crystal structure of the title compound, (I).

In (I) (Fig. 1), all bond lengths are normal (Allen et al., 1987) and in good agreement with those reported previously (Henschel et al., 1996). As can be seen from the packing diagram (Fig. 2), the crystal structure of (I) is stabilized by intermolecular N—H···O hydrogen bonding. The crystal packing is further stabilized by van der Waals forces

Experimental

A solution of naphthalene disulfonyl chloride (384 mg, 1 mmol) dissolved in anhydrous CH2Cl2 (10 ml), and dropwise added over a period of 10 min to a solution of propan-2-amine (118 mg, 2 mmol) in CH2Cl2 (10 ml) at 273 K. The mixture was stirred at r.t. for 4 h. The organic phase was washed with water twice, and dried over anhydrous Na2SO4. The solvent was removed and the residue was purified by flash chromatography (1:3 cyclohexane:dichloromethane) to give ) as a white solid (267 mg, 62%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol and dichloromethane at room temperature.

Refinement

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95–1.0 Å and N—H = 0.88 Å with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C,N).

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 40% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The packing of (I), viewed down the a axis, showing one layer of molecules connected by N—H···O hydrogen bonds (dashed lines).

Crystal data

C18H26N2O6S2F000 = 912
Mr = 430.53Dx = 1.337 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 875 reflections
a = 17.229 (3) Åθ = 2.2–27.5º
b = 7.2532 (15) ŵ = 0.28 mm1
c = 18.035 (4) ÅT = 173 (2) K
β = 108.35 (3)ºPlate, colorless
V = 2139.2 (8) Å30.50 × 0.38 × 0.22 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer4889 independent reflections
Radiation source: rotating anode4227 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.020
T = 173(2) Kθmax = 27.5º
ω scans at fixed χ = 45°θmin = 1.3º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)h = −22→22
Tmin = 0.871, Tmax = 0.940k = −9→9
8740 measured reflectionsl = −23→23

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.117  w = 1/[σ2(Fo2) + (0.0534P)2 + 0.9298P] where P = (Fo2 + 2Fc2)/3
S = 1.16(Δ/σ)max < 0.001
4889 reflectionsΔρmax = 0.36 e Å3
253 parametersΔρmin = −0.49 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.39879 (3)0.72730 (7)0.23076 (3)0.02292 (13)
S20.08210 (3)1.11117 (7)0.42543 (3)0.01969 (13)
O10.42832 (10)0.4396 (2)0.35142 (10)0.0368 (4)
O20.48381 (9)0.7597 (2)0.27099 (10)0.0365 (4)
O30.35149 (10)0.8610 (2)0.17682 (9)0.0325 (4)
O40.08620 (9)1.2491 (2)0.36997 (9)0.0277 (3)
O50.09471 (9)1.1659 (2)0.50512 (8)0.0261 (3)
O60.12159 (9)0.7784 (2)0.52066 (8)0.0268 (3)
N10.39535 (10)0.5367 (2)0.18585 (10)0.0232 (4)
H1A0.44150.47630.19330.028*
N2−0.00546 (10)1.0136 (2)0.39554 (9)0.0223 (4)
H2B−0.03581.00760.42660.027*
C10.33009 (13)0.5414 (3)0.41377 (13)0.0280 (5)
H1B0.34240.44130.44960.034*
C20.37011 (13)0.5567 (3)0.35894 (13)0.0262 (4)
C30.35006 (12)0.7046 (3)0.30358 (11)0.0212 (4)
C40.29442 (12)0.8349 (3)0.30760 (11)0.0209 (4)
H4B0.28230.93380.27120.025*
C50.25444 (11)0.8252 (3)0.36502 (11)0.0197 (4)
C60.19712 (11)0.9599 (3)0.37008 (11)0.0197 (4)
H6A0.18741.06400.33650.024*
C70.15537 (11)0.9418 (3)0.42305 (11)0.0190 (4)
C80.16906 (12)0.7855 (3)0.47337 (11)0.0215 (4)
C90.22660 (13)0.6566 (3)0.47142 (12)0.0247 (4)
H9A0.23700.55530.50660.030*
C100.27065 (12)0.6734 (3)0.41739 (11)0.0222 (4)
C110.4475 (2)0.2809 (4)0.40126 (18)0.0543 (8)
H11A0.49050.20930.38970.081*
H11B0.39850.20440.39220.081*
H11C0.46660.32070.45600.081*
C120.32048 (14)0.4553 (3)0.13290 (14)0.0336 (5)
H12A0.27810.55400.11560.040*
C130.28821 (17)0.3054 (4)0.1736 (2)0.0527 (8)
H13A0.27660.35730.21910.079*
H13B0.32920.20750.19050.079*
H13C0.23790.25410.13740.079*
C140.3397 (2)0.3816 (5)0.06177 (16)0.0605 (9)
H14A0.36030.48200.03680.091*
H14B0.28990.33050.02460.091*
H14C0.38130.28470.07800.091*
C150.12852 (15)0.6187 (3)0.56924 (14)0.0333 (5)
H15A0.09100.63040.60010.050*
H15B0.18480.60820.60440.050*
H15C0.11450.50830.53640.050*
C16−0.03619 (12)0.9332 (3)0.31603 (11)0.0237 (4)
H16A0.00850.94060.29170.028*
C17−0.10837 (15)1.0449 (4)0.26648 (13)0.0365 (6)
H17A−0.09151.17320.26420.055*
H17B−0.15271.04000.28970.055*
H17C−0.12760.99350.21350.055*
C18−0.05611 (15)0.7314 (3)0.32295 (13)0.0315 (5)
H18A−0.00710.66710.35530.047*
H18B−0.07460.67560.27080.047*
H18C−0.09950.72120.34720.047*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0250 (3)0.0202 (3)0.0293 (3)−0.00251 (19)0.0167 (2)−0.0004 (2)
S20.0251 (3)0.0173 (2)0.0197 (2)0.00184 (18)0.01134 (18)−0.00043 (19)
O10.0400 (9)0.0387 (10)0.0408 (9)0.0213 (8)0.0256 (8)0.0147 (8)
O20.0269 (8)0.0371 (10)0.0497 (10)−0.0128 (7)0.0179 (7)−0.0073 (8)
O30.0468 (10)0.0232 (8)0.0372 (9)0.0067 (7)0.0270 (8)0.0073 (7)
O40.0373 (8)0.0209 (8)0.0307 (8)0.0051 (6)0.0192 (7)0.0061 (6)
O50.0350 (8)0.0238 (8)0.0229 (7)−0.0010 (6)0.0143 (6)−0.0054 (6)
O60.0377 (9)0.0218 (8)0.0297 (8)0.0051 (6)0.0232 (7)0.0056 (6)
N10.0204 (8)0.0233 (9)0.0278 (9)0.0050 (7)0.0100 (7)−0.0020 (7)
N20.0211 (8)0.0296 (10)0.0197 (8)0.0004 (7)0.0114 (7)−0.0028 (7)
C10.0325 (12)0.0280 (12)0.0270 (10)0.0091 (9)0.0144 (9)0.0078 (9)
C20.0250 (10)0.0278 (11)0.0284 (10)0.0074 (8)0.0120 (8)0.0032 (9)
C30.0222 (10)0.0210 (10)0.0223 (9)−0.0023 (8)0.0099 (8)−0.0008 (8)
C40.0227 (10)0.0199 (10)0.0210 (9)−0.0019 (8)0.0084 (8)−0.0012 (8)
C50.0197 (9)0.0207 (10)0.0191 (9)−0.0006 (7)0.0069 (7)−0.0003 (8)
C60.0218 (10)0.0195 (10)0.0187 (9)−0.0003 (7)0.0076 (7)0.0015 (8)
C70.0208 (9)0.0173 (9)0.0193 (9)0.0009 (7)0.0070 (7)−0.0012 (7)
C80.0256 (10)0.0227 (10)0.0189 (9)−0.0004 (8)0.0108 (8)−0.0001 (8)
C90.0302 (11)0.0229 (11)0.0239 (10)0.0047 (8)0.0126 (9)0.0048 (8)
C100.0233 (10)0.0232 (10)0.0211 (9)0.0012 (8)0.0085 (8)−0.0003 (8)
C110.0676 (19)0.0501 (17)0.0593 (17)0.0394 (15)0.0400 (15)0.0280 (14)
C120.0292 (12)0.0283 (12)0.0356 (12)0.0092 (9)−0.0008 (9)−0.0077 (10)
C130.0341 (14)0.0359 (15)0.085 (2)−0.0089 (11)0.0150 (14)−0.0131 (15)
C140.066 (2)0.068 (2)0.0356 (14)0.0236 (17)0.0000 (14)−0.0182 (15)
C150.0495 (14)0.0233 (11)0.0372 (12)0.0038 (10)0.0281 (11)0.0065 (10)
C160.0251 (10)0.0297 (11)0.0182 (9)0.0022 (8)0.0097 (8)−0.0024 (8)
C170.0359 (13)0.0399 (14)0.0288 (11)0.0101 (10)0.0031 (10)0.0007 (10)
C180.0407 (13)0.0282 (12)0.0264 (11)−0.0013 (10)0.0119 (10)−0.0041 (9)

Geometric parameters (Å, °)

S1—O31.4324 (16)C8—C91.371 (3)
S1—O21.4345 (17)C9—C101.416 (3)
S1—N11.5937 (18)C9—H9A0.9500
S1—C31.775 (2)C11—H11A0.9800
S2—O41.4320 (15)C11—H11B0.9800
S2—O51.4402 (15)C11—H11C0.9800
S2—N21.5984 (18)C12—C131.512 (4)
S2—C71.772 (2)C12—C141.520 (4)
O1—C21.353 (2)C12—H12A1.0000
O1—C111.434 (3)C13—H13A0.9800
O6—C81.356 (2)C13—H13B0.9800
O6—C151.434 (3)C13—H13C0.9800
N1—C121.466 (3)C14—H14A0.9800
N1—H1A0.8800C14—H14B0.9800
N2—C161.483 (2)C14—H14C0.9800
N2—H2B0.8800C15—H15A0.9800
C1—C21.377 (3)C15—H15B0.9800
C1—C101.418 (3)C15—H15C0.9800
C1—H1B0.9500C16—C171.517 (3)
C2—C31.432 (3)C16—C181.517 (3)
C3—C41.364 (3)C16—H16A1.0000
C4—C51.415 (3)C17—H17A0.9800
C4—H4B0.9500C17—H17B0.9800
C5—C61.412 (3)C17—H17C0.9800
C5—C101.420 (3)C18—H18A0.9800
C6—C71.371 (3)C18—H18B0.9800
C6—H6A0.9500C18—H18C0.9800
C7—C81.424 (3)
O3—S1—O2120.31 (10)C1—C10—C5119.10 (18)
O3—S1—N1108.65 (10)O1—C11—H11A109.5
O2—S1—N1105.52 (10)O1—C11—H11B109.5
O3—S1—C3105.36 (9)H11A—C11—H11B109.5
O2—S1—C3106.66 (10)O1—C11—H11C109.5
N1—S1—C3110.17 (9)H11A—C11—H11C109.5
O4—S2—O5118.63 (9)H11B—C11—H11C109.5
O4—S2—N2108.82 (10)N1—C12—C13110.9 (2)
O5—S2—N2106.76 (9)N1—C12—C14108.1 (2)
O4—S2—C7105.99 (9)C13—C12—C14111.5 (2)
O5—S2—C7109.31 (9)N1—C12—H12A108.8
N2—S2—C7106.79 (9)C13—C12—H12A108.8
C2—O1—C11118.22 (18)C14—C12—H12A108.8
C8—O6—C15117.67 (16)C12—C13—H13A109.5
C12—N1—S1124.38 (14)C12—C13—H13B109.5
C12—N1—H1A117.8H13A—C13—H13B109.5
S1—N1—H1A117.8C12—C13—H13C109.5
C16—N2—S2120.79 (13)H13A—C13—H13C109.5
C16—N2—H2B119.6H13B—C13—H13C109.5
S2—N2—H2B119.6C12—C14—H14A109.5
C2—C1—C10120.7 (2)C12—C14—H14B109.5
C2—C1—H1B119.6H14A—C14—H14B109.5
C10—C1—H1B119.6C12—C14—H14C109.5
O1—C2—C1125.2 (2)H14A—C14—H14C109.5
O1—C2—C3115.08 (18)H14B—C14—H14C109.5
C1—C2—C3119.73 (19)O6—C15—H15A109.5
C4—C3—C2120.08 (18)O6—C15—H15B109.5
C4—C3—S1118.62 (15)H15A—C15—H15B109.5
C2—C3—S1121.27 (15)O6—C15—H15C109.5
C3—C4—C5121.11 (19)H15A—C15—H15C109.5
C3—C4—H4B119.4H15B—C15—H15C109.5
C5—C4—H4B119.4N2—C16—C17109.64 (17)
C6—C5—C4121.62 (18)N2—C16—C18108.73 (17)
C6—C5—C10119.25 (17)C17—C16—C18113.51 (19)
C4—C5—C10119.10 (18)N2—C16—H16A108.3
C7—C6—C5120.63 (18)C17—C16—H16A108.3
C7—C6—H6A119.7C18—C16—H16A108.3
C5—C6—H6A119.7C16—C17—H17A109.5
C6—C7—C8120.15 (18)C16—C17—H17B109.5
C6—C7—S2118.97 (15)H17A—C17—H17B109.5
C8—C7—S2120.84 (14)C16—C17—H17C109.5
O6—C8—C9125.04 (18)H17A—C17—H17C109.5
O6—C8—C7114.81 (17)H17B—C17—H17C109.5
C9—C8—C7120.14 (18)C16—C18—H18A109.5
C8—C9—C10120.50 (19)C16—C18—H18B109.5
C8—C9—H9A119.8H18A—C18—H18B109.5
C10—C9—H9A119.8C16—C18—H18C109.5
C9—C10—C1121.66 (19)H18A—C18—H18C109.5
C9—C10—C5119.23 (18)H18B—C18—H18C109.5
O3—S1—N1—C12−45.7 (2)C5—C6—C7—S2−178.34 (15)
O2—S1—N1—C12−175.98 (18)O4—S2—C7—C6−3.88 (19)
C3—S1—N1—C1269.3 (2)O5—S2—C7—C6−132.83 (16)
O4—S2—N2—C1653.43 (18)N2—S2—C7—C6112.02 (16)
O5—S2—N2—C16−177.42 (15)O4—S2—C7—C8178.22 (16)
C7—S2—N2—C16−60.57 (18)O5—S2—C7—C849.27 (18)
C11—O1—C2—C13.5 (4)N2—S2—C7—C8−65.88 (18)
C11—O1—C2—C3−175.7 (2)C15—O6—C8—C9−3.8 (3)
C10—C1—C2—O1179.1 (2)C15—O6—C8—C7176.08 (18)
C10—C1—C2—C3−1.7 (3)C6—C7—C8—O6−177.07 (18)
O1—C2—C3—C4−177.49 (19)S2—C7—C8—O60.8 (2)
C1—C2—C3—C43.2 (3)C6—C7—C8—C92.8 (3)
O1—C2—C3—S10.4 (3)S2—C7—C8—C9−179.31 (16)
C1—C2—C3—S1−178.88 (18)O6—C8—C9—C10177.37 (19)
O3—S1—C3—C4−14.70 (19)C7—C8—C9—C10−2.5 (3)
O2—S1—C3—C4114.23 (17)C8—C9—C10—C1−179.6 (2)
N1—S1—C3—C4−131.72 (16)C8—C9—C10—C5−0.1 (3)
O3—S1—C3—C2167.35 (17)C2—C1—C10—C9177.6 (2)
O2—S1—C3—C2−63.72 (19)C2—C1—C10—C5−1.8 (3)
N1—S1—C3—C250.3 (2)C6—C5—C10—C92.5 (3)
C2—C3—C4—C5−1.2 (3)C4—C5—C10—C9−175.71 (19)
S1—C3—C4—C5−179.20 (15)C6—C5—C10—C1−178.05 (19)
C3—C4—C5—C6179.59 (19)C4—C5—C10—C13.7 (3)
C3—C4—C5—C10−2.2 (3)S1—N1—C12—C13−100.2 (2)
C4—C5—C6—C7175.95 (18)S1—N1—C12—C14137.2 (2)
C10—C5—C6—C7−2.2 (3)S2—N2—C16—C17−111.90 (18)
C5—C6—C7—C8−0.4 (3)S2—N2—C16—C18123.47 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.882.002.821 (2)154
N2—H2B···O5ii0.882.223.001 (2)148
N2—H2B···O6ii0.882.533.235 (2)138

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x, −y+2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2423).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Henschel, D., Hiemisch, O., Blaschette, A. & Jones, P. G. (1996). Z. Naturforsch. Teil B, 51, 1313–1315.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Kamoshita, K., Matsumoto, H. & Nagano, E. (1987). US Patent No. 4 670 046.
  • Rigaku (2004). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhang, Z. B., Zhou, S. Y. & Nie, J. (2007). J. Mol. Catal. A Chem.265, 9–14.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography