Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 7| July 2008| Page o1204
doi:10.1107/S1600536808016164

N-Cyclo­do­decyl-5-(di­methyl­amino)­naphthalene-1-sulfonamide

Conrad Fischer,a Tobias Gruber,a Wilhelm Seichter,a Edwin Webera and Bakhtiyar T. Ibragimovb*

aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany, and bInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, H Abdullaev 83, Tashkent 100125, Uzbekistan
*Correspondence e-mail: bahtier@academy.uzsci.net

(Received 31 March 2008; accepted 28 May 2008; online 7 June 2008)

The molecule of the title compound, C24H36N2O2S, displays a U-shaped conformation. The prominent inter­molecular inter­actions are N—H⋯O hydrogen bonds, resulting in the formation of dimers. Additional C—H⋯π contacts involving one of the methyl­ene groups of the macrocycle and the naphthalene rings of a neighbouring mol­ecule stabilize the packing structure. In the crystal structure, the cyclo­dodecyl ring is disordered over two positions; the site occupancy factors are ca 0.86 and 0.14.

Related literature

For general background, see: Weber et al. (2004[Weber, E., Kunze, D. & Seichter, W. (2004). Acta Cryst. E60, o2331-o2333.]); Schönefeld et al. (2005[Schönefeld, K., Barann, A., Vogel, K., Feller, K.-H., Kunze, D., Müller, P. & Weber, E. (2005). Int. J. Environ. Anal. Chem. 85, 655-663.]); Gruber et al. (2008[Gruber, T., Seichter, W. & Weber, E. (2008). Supramol. Chem. In the press. ]). For C—H⋯π contacts, see: Nishio (2004[Nishio, M. (2004). CrystEngComm, 6, 130-158.]). For related structures, see: Dunitz & Shearer (1960[Dunitz, J. D. & Shearer, H. M. M. (1960). Helv. Chim. Acta, 43, 18-35.]); Rudert et al. (1994[Rudert, R., Vollhardt, D. & Czichocki, G. (1994). Acta Cryst. C50, 1054-1057.]); Feiler et al. (1995[Feiler, L., Langhals, H. & Polborn, K. (1995). Liebigs Ann. pp. 1229-1244.]).

[Scheme 1]

Experimental

Crystal data

  • C24H36N2O2S

  • Mr = 416.62

  • Monoclinic, P 21 /c

  • a = 10.3564 (3) Å

  • b = 13.5117 (4) Å

  • c = 16.2076 (4) Å

  • β = 95.814 (1)°

  • V = 2256.30 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.17 mm−1

  • T = 93 (2) K

  • 0.54 × 0.42 × 0.29 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi scan (SADABS; Sheldrick, 2002[Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.]) Tmin = 0.826, Tmax = 0.954

  • 71103 measured reflections

  • 14866 independent reflections

  • 10604 reflections with I > 2σ(I)

  • Rint = 0.034
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.120

  • S = 1.02

  • 14866 reflections

  • 469 parameters

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

  • Δρmax = 0.46 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯O1i 0.83 (1) 2.28 (1) 3.065 (1) 154 (1)
C4—H4⋯O1 0.95 2.34 3.026 (1) 128
C20—H20A⋯CgAii 1.03 (1) 2.88 (1) 3.595 (1) 126 (1)
C20—H20B⋯CgBii 0.96 (1) 2.84 (1) 3.613 (1) 140 (1)
C20A—H20D⋯CgBii 0.99 2.81 3.792 (1) 170
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x+1, y, z. CgA and CgB are the centroids of the C1–C5/C10 and C5–C10 benzene rings, respectively.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016164/xu2416sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808016164/xu2416Isup2.hkl

checkCIF report


Comment top

The title compound (I) was prepared as part of our studies concerning fluorogenic receptor molecules with possible analytical applications (Weber et al., 2004; Schönefeld et al., 2005; Gruber et al., 2008).

The molecular geometry of the molecule (figure 1) is best described by an angular conformation, whereas the cyclododecyl ring is disordered over two positions giving rise to an entirely filled cavity. The torsion angle are 71.44 (6)° (C6—S1—N2—C13) and 51.5 (3)° (C6—S1—N2—C13A), respectively, while the mean planes of the cyclododecylamine and the naphthalene include an angle of 20.1°. Weak C—H···π contacts (Nishio, 2004) involving one methylene group of the cycloalkyl ring and the two aromatic rings, and a C—H···O interaction between H4 and O1 stabilize the crystal packing. Furthermore, N—H···O hydrogen bonding leads to dimerization similar to carboxylic acids. The equatorial arrangement and conformation of the cyclododecyl moiety correspond to reported data (Dunitz & Shearer, 1960; Rudert et al., 1994; Feiler et al., 1995).

Related literature top

For general background, see: Weber et al. (2004); Schönefeld et al. (2005); Gruber et al. (2008). For C—H···π contacts, see: Nishio (2004). For related structures, see: Dunitz & Shearer (1960); Rudert et al. (1994); Feiler et al. (1995).

Experimental top

To a solution of cyclododecylamine (8.18 mmol) and triethylamine (14.39 mmol) in THF (50 ml), dansylchloride (9.63 mmol) in THF (50 ml) was added dropwise and refluxed for 2 h. After evaporation of the solvent under reduced pressure, the residue was dissolved in water/chloroform (100 ml of each). The organic extract was dried (Na2SO4) and the solvent distilled off. Recrystallization from n-hexane/dichloromethane (1:1) yielded light yellow crystals. (34%). Anal. Calcd. for C24H36N2O2S: C, 69.19; H, 8.71; N, 6.72; Found: C, 69.21; H, 8.83; N, 7.00%.

Refinement top

The cyclododecyl ring is disordered over two positions and refinement of occupancies converged to 0.8623:1377. H atoms of the major component of the disordered cyclododecyl were located in a difference Fourier map and refined isotropically. Imino H atom was also located in a difference Fourier map and refined isotropically. Other H atoms were positioned geometrically and allowed to ride on their parent atoms, with C–H = 0.95 - 0.99 Å, and refined in a riding mode with Uiso(H) = 1.2 or 1.5Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with 30% probability displacement ellipsoids.
N-Cyclododecyl-5-(dimethylamino)naphthalene-1-sulfonamide top
Crystal data top
C24H36N2O2SF(000) = 904
Mr = 416.62Dx = 1.227 Mg m−3
Monoclinic, P21/cMelting point: 437 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.3564 (3) ÅCell parameters from 9249 reflections
b = 13.5117 (4) Åθ = 2.5–39.0°
c = 16.2076 (4) ŵ = 0.17 mm−1
β = 95.814 (1)°T = 93 K
V = 2256.30 (11) Å3Plate, light yellow
Z = 40.54 × 0.42 × 0.29 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer		14866 independent reflections
Radiation source: fine-focus sealed tube10604 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ϕ and ω scansθmax = 41.0°, θmin = 2.0°
Absorption correction: multi scan
(SADABS; Sheldrick, 2002)		h = −18→19
Tmin = 0.826, Tmax = 0.954k = −24→24
71103 measured reflectionsl = −29→29
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0655P)2 + 0.1633P]
where P = (Fo2 + 2Fc2)/3
14866 reflections(Δ/σ)max < 0.001
469 parametersΔρmax = 0.46 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
Crystal data top
C24H36N2O2SV = 2256.30 (11) Å3
Mr = 416.62Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.3564 (3) ŵ = 0.17 mm−1
b = 13.5117 (4) ÅT = 93 K
c = 16.2076 (4) Å0.54 × 0.42 × 0.29 mm
β = 95.814 (1)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer		14866 independent reflections
Absorption correction: multi scan
(SADABS; Sheldrick, 2002)		10604 reflections with I > 2σ(I)
Tmin = 0.826, Tmax = 0.954Rint = 0.034
71103 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.46 e Å−3
14866 reflectionsΔρmin = −0.26 e Å−3
469 parameters
Special details top

Experimental. 1H NMR (400 MHz, CDCl3, δ, p.p.m.): 0.95 (4H, m, CH2, 1.09 (4H, m, CH2), 1.20 (12H, m, CH2), 1.41 (2H, m, CH2), 2.88 (6H, s, N(CH3)2), 3.20 (1H, m, CHNH), 4.57 (1H, s, CHNH), 7.17 (1H, d, ArH), 7.53 (2H, d, ArH), 8.32 (2H, m, ArH), 8.52 (1H, d, ArH). 13C NMR (100 MHz, CDCl3, δ, p.p.m.): 21.09, 23.06, 23.17, 23.24, 23.52, 31.13 (CH2), 45.36 (N(CH3)2), 50.53 (CHNH), 115.03 (6-ArC), 119.00, 123.09 (2-, 8-ArC), 128.21, 129.61, 129.76, 129.84, 130.24 (3-,4-,4a-,7-,8a-ArC), 135.57 (1-ArC), 151.89 (5-ArC). IR (KBr): 3290 (N—H); 3076, 3051 (C—Har); 2937, 2862 (C—Halk); 2787 (N—CH3); 1620, 1592, 1574 (C?C); 1474; 1453; 1413; 1356; 1313; 1231; 1206; 1164; 1150; 1092; 1074; 1060; 1028; 946; 882; 792; 689; 632; 578.

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) top
xyzUiso*/UeqOcc. (<1)
S10.039201 (15)0.332136 (11)0.456193 (9)0.01773 (4)
O1−0.06052 (5)0.36676 (4)0.50517 (3)0.02297 (10)
O20.11146 (5)0.24527 (4)0.48235 (3)0.02405 (10)
N1−0.23380 (5)0.42906 (4)0.08519 (3)0.01851 (9)
N20.14083 (5)0.42236 (4)0.45239 (3)0.01769 (9)
H2'0.1060 (11)0.4782 (9)0.4485 (7)0.034 (3)*
C1−0.21013 (5)0.44354 (4)0.17181 (4)0.01559 (9)
C2−0.25882 (6)0.52375 (5)0.21154 (4)0.01812 (10)
H2−0.31100.57120.18040.022*
C3−0.23173 (7)0.53578 (5)0.29785 (4)0.01954 (11)
H3−0.26710.59090.32420.023*
C4−0.15557 (6)0.46971 (5)0.34466 (4)0.01791 (10)
H4−0.13600.48070.40250.021*
C5−0.10584 (6)0.38498 (4)0.30710 (4)0.01552 (9)
C6−0.02721 (6)0.31162 (4)0.35209 (4)0.01712 (10)
C70.01112 (7)0.22697 (5)0.31416 (4)0.02077 (11)
H70.06360.17960.34520.025*
C8−0.02742 (7)0.21044 (5)0.22930 (5)0.02228 (12)
H8−0.00400.15060.20390.027*
C9−0.09844 (6)0.28033 (5)0.18340 (4)0.01948 (10)
H9−0.12270.26870.12610.023*
C10−0.13641 (5)0.36992 (4)0.21999 (4)0.01529 (9)
C11−0.11742 (7)0.43858 (6)0.04101 (4)0.02615 (13)
H11A−0.09450.50870.03700.039*
H11B−0.13490.4107−0.01480.039*
H11C−0.04530.40270.07140.039*
C12−0.33772 (7)0.48886 (6)0.04336 (4)0.02499 (13)
H12A−0.41450.48480.07390.037*
H12B−0.35930.4641−0.01320.037*
H12C−0.30920.55790.04130.037*
C130.26599 (10)0.40723 (8)0.41631 (6)0.01599 (15)0.8623 (12)
H130.2564 (11)0.3489 (8)0.3830 (7)0.015 (2)*0.8623 (12)
C140.29031 (8)0.49533 (6)0.36018 (5)0.01951 (13)0.8623 (12)
H14A0.3902 (12)0.5005 (9)0.3563 (7)0.026 (3)*0.8623 (12)
H14B0.2651 (13)0.5557 (10)0.3868 (8)0.031 (3)*0.8623 (12)
C150.21831 (8)0.48964 (6)0.27273 (5)0.02269 (15)0.8623 (12)
H15A0.1238 (12)0.4829 (9)0.2768 (7)0.025 (3)*0.8623 (12)
H15B0.2324 (13)0.5552 (10)0.2449 (8)0.031 (3)*0.8623 (12)
C160.25964 (11)0.40350 (9)0.21972 (7)0.02426 (19)0.8623 (12)
H16A0.2467 (12)0.3403 (9)0.2514 (8)0.020 (3)*0.8623 (12)
H16B0.2029 (13)0.4015 (10)0.1665 (8)0.032 (3)*0.8623 (12)
C170.39987 (9)0.40970 (6)0.19824 (5)0.02443 (15)0.8623 (12)
H17A0.4599 (12)0.4308 (9)0.2472 (8)0.026 (3)*0.8623 (12)
H17B0.4033 (14)0.4678 (11)0.1564 (9)0.041 (4)*0.8623 (12)
C180.45099 (12)0.31286 (7)0.16479 (6)0.02798 (18)0.8623 (12)
H18A0.5359 (15)0.3266 (11)0.1369 (9)0.040 (4)*0.8623 (12)
H18B0.3903 (16)0.2865 (13)0.1204 (10)0.051 (4)*0.8623 (12)
C190.47808 (14)0.23333 (9)0.23171 (8)0.0257 (2)0.8623 (12)
H19A0.4022 (12)0.2275 (9)0.2587 (8)0.027 (3)*0.8623 (12)
H19B0.4843 (15)0.1656 (11)0.2067 (9)0.042 (4)*0.8623 (12)
C200.59746 (8)0.25578 (6)0.29262 (6)0.02371 (15)0.8623 (12)
H20A0.6066 (13)0.3314 (9)0.2995 (8)0.027 (3)*0.8623 (12)
H20B0.6733 (13)0.2330 (10)0.2690 (8)0.033 (3)*0.8623 (12)
C210.59636 (9)0.20577 (6)0.37710 (6)0.02530 (16)0.8623 (12)
H21A0.5887 (13)0.1346 (10)0.3676 (8)0.032 (3)*0.8623 (12)
H21B0.6813 (12)0.2197 (9)0.4102 (8)0.025 (3)*0.8623 (12)
C220.48776 (10)0.24042 (7)0.42801 (6)0.02177 (15)0.8623 (12)
H22A0.4013 (12)0.2295 (9)0.3935 (7)0.024 (3)*0.8623 (12)
H22B0.4854 (13)0.1965 (10)0.4788 (8)0.030 (3)*0.8623 (12)
C230.50024 (8)0.34853 (6)0.45558 (5)0.02195 (14)0.8623 (12)
H23A0.5261 (11)0.3903 (9)0.4092 (7)0.022 (3)*0.8623 (12)
H23B0.5757 (12)0.3529 (9)0.4994 (8)0.027 (3)*0.8623 (12)
C240.37593 (8)0.39027 (6)0.48608 (5)0.01908 (13)0.8623 (12)
H24A0.3437 (12)0.3419 (8)0.5269 (8)0.021 (3)*0.8623 (12)
H24B0.3937 (12)0.4520 (9)0.5149 (8)0.026 (3)*0.8623 (12)
C13A0.2423 (7)0.4184 (5)0.3938 (4)0.0194 (11)0.1377 (12)
H13A0.24600.34920.37220.023*0.1377 (12)
C14A0.2135 (5)0.4874 (4)0.3205 (3)0.0217 (9)0.1377 (12)
H14C0.22740.55660.33960.026*0.1377 (12)
H14D0.12110.48050.29890.026*0.1377 (12)
C15A0.2983 (6)0.4673 (4)0.2497 (4)0.0269 (10)0.1377 (12)
H15C0.28390.52080.20810.032*0.1377 (12)
H15D0.39070.46970.27240.032*0.1377 (12)
C16A0.2720 (8)0.3687 (6)0.2067 (5)0.0289 (13)0.1377 (12)
H16C0.18880.37270.17100.035*0.1377 (12)
H16D0.26290.31710.24910.035*0.1377 (12)
C17A0.3806 (6)0.3380 (5)0.1532 (4)0.0292 (11)0.1377 (12)
H17C0.35000.28050.11860.035*0.1377 (12)
H17D0.39590.39320.11520.035*0.1377 (12)
C18A0.5089 (6)0.3109 (4)0.2021 (4)0.0262 (10)0.1377 (12)
H18C0.57390.30060.16210.031*0.1377 (12)
H18D0.53800.36840.23700.031*0.1377 (12)
C19A0.5103 (9)0.2219 (7)0.2568 (5)0.0290 (14)0.1377 (12)
H19C0.52240.16290.22220.035*0.1377 (12)
H19D0.42350.21600.27700.035*0.1377 (12)
C20A0.6097 (5)0.2175 (4)0.3309 (3)0.0226 (9)0.1377 (12)
H20C0.69650.22900.31210.027*0.1377 (12)
H20D0.60940.15000.35460.027*0.1377 (12)
C21A0.5887 (5)0.2918 (4)0.3989 (3)0.0226 (9)0.1377 (12)
H21C0.66770.29340.43880.027*0.1377 (12)
H21D0.57790.35840.37360.027*0.1377 (12)
C22A0.4735 (6)0.2708 (5)0.4459 (4)0.0227 (10)0.1377 (12)
H22C0.40060.24940.40560.027*0.1377 (12)
H22D0.49580.21450.48370.027*0.1377 (12)
C23A0.4269 (5)0.3538 (4)0.4958 (3)0.0227 (9)0.1377 (12)
H23C0.50090.37870.53350.027*0.1377 (12)
H23D0.36140.32770.53050.027*0.1377 (12)
C24A0.3680 (5)0.4397 (4)0.4452 (3)0.0220 (9)0.1377 (12)
H24C0.35350.49480.48350.026*0.1377 (12)
H24D0.43170.46280.40780.026*0.1377 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01813 (7)0.01768 (7)0.01798 (6)0.00164 (5)0.00484 (5)0.00483 (5)
O10.0224 (2)0.0277 (2)0.0202 (2)0.00305 (18)0.00882 (17)0.00475 (17)
O20.0248 (2)0.0197 (2)0.0278 (2)0.00326 (17)0.00366 (18)0.00930 (18)
N10.0155 (2)0.0247 (2)0.01568 (19)0.00039 (17)0.00316 (16)−0.00216 (17)
N20.0186 (2)0.0165 (2)0.0185 (2)0.00146 (17)0.00489 (17)0.00115 (16)
C10.0131 (2)0.0173 (2)0.0167 (2)−0.00111 (17)0.00304 (17)−0.00180 (17)
C20.0187 (2)0.0171 (2)0.0185 (2)0.00267 (19)0.00184 (19)−0.00127 (19)
C30.0226 (3)0.0173 (2)0.0189 (2)0.0045 (2)0.0028 (2)−0.00262 (19)
C40.0204 (2)0.0166 (2)0.0170 (2)0.00290 (19)0.00259 (19)−0.00208 (18)
C50.0148 (2)0.0140 (2)0.0182 (2)−0.00004 (17)0.00383 (17)−0.00080 (17)
C60.0167 (2)0.0147 (2)0.0205 (2)0.00090 (18)0.00426 (18)0.00131 (18)
C70.0205 (3)0.0149 (2)0.0275 (3)0.00235 (19)0.0049 (2)0.0006 (2)
C80.0221 (3)0.0164 (2)0.0290 (3)0.0023 (2)0.0058 (2)−0.0049 (2)
C90.0182 (2)0.0176 (2)0.0231 (3)−0.00017 (19)0.0049 (2)−0.0059 (2)
C100.0136 (2)0.0147 (2)0.0181 (2)−0.00075 (16)0.00396 (17)−0.00231 (17)
C110.0223 (3)0.0366 (4)0.0209 (3)0.0001 (3)0.0090 (2)−0.0012 (3)
C120.0225 (3)0.0328 (3)0.0192 (3)0.0043 (2)−0.0004 (2)−0.0007 (2)
C130.0180 (4)0.0155 (3)0.0149 (4)0.0001 (3)0.0041 (3)−0.0004 (3)
C140.0211 (3)0.0178 (3)0.0202 (3)−0.0010 (2)0.0051 (2)0.0013 (2)
C150.0194 (3)0.0273 (4)0.0217 (3)0.0012 (3)0.0042 (2)0.0074 (3)
C160.0239 (4)0.0321 (5)0.0170 (4)−0.0055 (4)0.0032 (3)0.0019 (4)
C170.0291 (4)0.0230 (3)0.0230 (3)−0.0026 (3)0.0113 (3)0.0045 (3)
C180.0400 (6)0.0270 (4)0.0185 (3)−0.0025 (4)0.0104 (4)−0.0012 (3)
C190.0334 (6)0.0189 (4)0.0258 (5)−0.0070 (4)0.0072 (4)−0.0033 (4)
C200.0234 (3)0.0205 (3)0.0289 (4)−0.0014 (3)0.0111 (3)−0.0005 (3)
C210.0275 (4)0.0203 (3)0.0292 (4)0.0075 (3)0.0080 (3)0.0018 (3)
C220.0267 (4)0.0159 (3)0.0237 (4)0.0017 (3)0.0076 (3)0.0011 (3)
C230.0187 (3)0.0197 (3)0.0271 (3)0.0014 (2)0.0011 (3)−0.0044 (3)
C240.0201 (3)0.0196 (3)0.0172 (3)0.0015 (3)0.0002 (2)−0.0037 (2)
C13A0.018 (3)0.020 (2)0.020 (3)0.0042 (18)0.002 (2)0.002 (2)
C14A0.027 (2)0.0186 (19)0.020 (2)0.0021 (16)0.0067 (16)0.0068 (15)
C15A0.029 (2)0.023 (2)0.031 (2)0.0003 (18)0.012 (2)0.0089 (18)
C16A0.023 (3)0.036 (4)0.028 (3)−0.007 (3)0.002 (2)0.001 (3)
C17A0.029 (3)0.040 (3)0.020 (2)−0.002 (2)0.0107 (19)0.007 (2)
C18A0.030 (3)0.026 (2)0.024 (2)−0.0026 (19)0.012 (2)0.0017 (18)
C19A0.033 (4)0.028 (3)0.027 (3)−0.007 (3)0.011 (3)−0.006 (3)
C20A0.027 (2)0.0194 (19)0.022 (2)0.0026 (16)0.0073 (17)0.0040 (17)
C21A0.0190 (19)0.024 (2)0.025 (2)0.0020 (16)0.0036 (16)−0.0023 (17)
C22A0.024 (2)0.021 (2)0.023 (2)0.0085 (19)0.0006 (18)0.0006 (19)
C23A0.0167 (19)0.026 (2)0.024 (2)0.0079 (17)−0.0056 (15)−0.0060 (17)
C24A0.0172 (18)0.0193 (19)0.029 (2)0.0022 (15)−0.0011 (16)−0.0050 (17)
Geometric parameters (Å, º) top
S1—O21.4328 (5)C19—H19A0.941 (13)
S1—O11.4428 (5)C19—H19B1.006 (15)
S1—N21.6157 (6)C20—C211.5280 (13)
S1—C61.7781 (7)C20—H20A1.031 (12)
N1—C11.4140 (8)C20—H20B0.959 (14)
N1—C121.4570 (9)C21—C221.5340 (13)
N1—C111.4687 (8)C21—H21A0.975 (13)
N2—C13A1.487 (7)C21—H21B1.001 (12)
N2—C131.4891 (12)C22—C231.5292 (13)
N2—H2'0.835 (12)C22—H22A1.017 (12)
C1—C21.3818 (8)C22—H22B1.017 (13)
C1—C101.4357 (9)C23—C241.5326 (11)
C2—C31.4080 (9)C23—H23A0.997 (12)
C2—H20.9500C23—H23B1.003 (13)
C3—C41.3686 (9)C24—H24A1.011 (12)
C3—H30.9500C24—H24B0.965 (13)
C4—C51.4178 (8)C13A—C24A1.501 (8)
C4—H40.9500C13A—C14A1.516 (8)
C5—C101.4298 (8)C13A—H130.968 (13)
C5—C61.4341 (8)C13A—H13A1.0000
C6—C71.3760 (9)C14A—C15A1.538 (7)
C7—C81.4105 (10)C14A—H14C0.9900
C7—H70.9500C14A—H14D0.9900
C8—C91.3694 (10)C15A—C16A1.516 (10)
C8—H80.9500C15A—H15C0.9900
C9—C101.4209 (8)C15A—H15D0.9900
C9—H90.9500C16A—C17A1.545 (10)
C11—H11A0.9800C16A—H16C0.9900
C11—H11B0.9800C16A—H16D0.9900
C11—H11C0.9800C17A—C18A1.521 (9)
C12—H12A0.9800C17A—H17C0.9900
C12—H12B0.9800C17A—H17D0.9900
C12—H12C0.9800C18A—C19A1.494 (10)
C13—C141.5344 (12)C18A—H18C0.9900
C13—C241.5384 (13)C18A—H18D0.9900
C13—H130.954 (11)C19A—C20A1.501 (10)
C14—C151.5352 (12)C19A—H19C0.9900
C14—H14A1.045 (12)C19A—H19D0.9900
C14—H14B0.970 (13)C20A—C21A1.523 (7)
C15—C161.5331 (15)C20A—H20C0.9900
C15—H15A0.991 (12)C20A—H20D0.9900
C15—H15B1.012 (13)C21A—C22A1.507 (8)
C16—C171.5296 (14)C21A—H21C0.9900
C16—H16A1.012 (12)C21A—H21D0.9900
C16—H16B0.994 (13)C22A—C23A1.490 (8)
C17—C181.5312 (13)C22A—H22C0.9900
C17—H17A0.998 (13)C22A—H22D0.9900
C17—H17B1.040 (15)C23A—C24A1.513 (7)
C18—C191.5324 (16)C23A—H23C0.9900
C18—H18A1.045 (15)C23A—H23D0.9900
C18—H18B0.974 (17)C24A—H24C0.9900
C19—C201.5323 (16)C24A—H24D0.9900
O2—S1—O1118.96 (3)C22—C21—H21B107.9 (7)
O2—S1—N2107.86 (3)H21A—C21—H21B108.9 (11)
O1—S1—N2106.36 (3)C23—C22—C21113.82 (7)
O2—S1—C6107.06 (3)C23—C22—H22A110.1 (7)
O1—S1—C6110.06 (3)C21—C22—H22A108.2 (7)
N2—S1—C6105.80 (3)C23—C22—H22B109.2 (7)
C1—N1—C12115.52 (5)C21—C22—H22B109.6 (8)
C1—N1—C11113.81 (5)H22A—C22—H22B105.6 (10)
C12—N1—C11109.18 (6)C22—C23—C24113.38 (7)
C13A—N2—S1120.1 (3)C22—C23—H23A110.0 (7)
C13—N2—S1120.51 (5)C24—C23—H23A109.5 (7)
C13A—N2—H2'108.1 (8)C22—C23—H23B107.4 (7)
C13—N2—H2'118.7 (8)C24—C23—H23B111.7 (7)
S1—N2—H2'114.0 (8)H23A—C23—H23B104.5 (10)
C2—C1—N1122.44 (6)C23—C24—C13113.65 (7)
C2—C1—C10119.27 (5)C23—C24—H24A108.5 (7)
N1—C1—C10118.25 (5)C13—C24—H24A108.0 (7)
C1—C2—C3120.54 (6)C23—C24—H24B110.5 (7)
C1—C2—H2119.7C13—C24—H24B108.5 (7)
C3—C2—H2119.7H24A—C24—H24B107.6 (10)
C4—C3—C2121.40 (6)N2—C13A—C24A105.5 (5)
C4—C3—H3119.3N2—C13A—C14A112.5 (5)
C2—C3—H3119.3C24A—C13A—C14A114.0 (6)
C3—C4—C5120.18 (6)C24A—C13A—H1398.5 (9)
C3—C4—H4119.9N2—C13A—H13A108.2
C5—C4—H4119.9C13A—C14A—C15A113.2 (5)
C4—C5—C10119.02 (5)C13A—C14A—H14C108.9
C4—C5—C6123.51 (5)C15A—C14A—H14C108.9
C10—C5—C6117.47 (5)H15A—C14A—H14C109.7
C7—C6—C5121.47 (6)C13A—C14A—H14D108.9
C7—C6—S1116.88 (5)C15A—C14A—H14D108.9
C5—C6—S1121.32 (4)H14C—C14A—H14D107.8
C6—C7—C8120.09 (6)C16A—C15A—C14A114.1 (5)
C6—C7—H7120.0C16A—C15A—H15C108.7
C8—C7—H7120.0C14A—C15A—H15C108.7
C9—C8—C7120.25 (6)C16A—C15A—H15D108.7
C9—C8—H8119.9C14A—C15A—H15D108.7
C7—C8—H8119.9H15C—C15A—H15D107.6
C8—C9—C10121.13 (6)C15A—C16A—C17A112.8 (6)
C8—C9—H9119.4C15A—C16A—H16C109.0
C10—C9—H9119.4C17A—C16A—H16C109.0
C9—C10—C5119.36 (6)C15A—C16A—H16D109.0
C9—C10—C1121.17 (5)C17A—C16A—H16D109.0
C5—C10—C1119.40 (5)H16C—C16A—H16D107.8
N2—C13—C14109.15 (7)C18A—C17A—C16A114.7 (5)
N2—C13—C24109.92 (7)C18A—C17A—H17C108.6
C14—C13—C24113.43 (8)C16A—C17A—H17C108.6
N2—C13—H13106.9 (7)C18A—C17A—H17D108.6
C14—C13—H13108.6 (7)C16A—C17A—H17D108.6
C24—C13—H13108.6 (7)H17C—C17A—H17D107.6
C13—C14—C15114.52 (7)C19A—C18A—H18C108.0
C13—C14—H14A108.1 (7)C17A—C18A—H18C108.0
C15—C14—H14A109.8 (7)C19A—C18A—H18D108.0
C13—C14—H14B108.7 (8)C17A—C18A—H18D108.0
C15—C14—H14B109.0 (8)H18C—C18A—H18D107.2
H14A—C14—H14B106.4 (10)C18A—C19A—C20A118.1 (7)
C16—C15—C14114.73 (7)C18A—C19A—H19C107.8
C16—C15—H15A107.5 (7)C20A—C19A—H19C107.8
C14—C15—H15A109.5 (7)C18A—C19A—H19D107.8
C16—C15—H15B110.7 (7)C20A—C19A—H19D107.8
C14—C15—H15B106.8 (7)H19C—C19A—H19D107.1
H15A—C15—H15B107.3 (10)C19A—C20A—C21A114.6 (5)
C17—C16—C15114.29 (9)C19A—C20A—H20C108.6
C17—C16—H16A109.8 (7)C21A—C20A—H20C108.6
C15—C16—H16A107.3 (7)C19A—C20A—H20D108.6
C17—C16—H16B107.1 (8)C21A—C20A—H20D108.6
C15—C16—H16B109.5 (8)H20C—C20A—H20D107.6
H16A—C16—H16B108.7 (10)C22A—C21A—C20A114.9 (5)
C16—C17—C18113.83 (8)C22A—C21A—H21C108.6
C16—C17—H17A111.3 (7)C20A—C21A—H21C108.6
C18—C17—H17A108.4 (7)C22A—C21A—H21D108.6
C16—C17—H17B106.6 (8)C20A—C21A—H21D108.6
C18—C17—H17B112.2 (8)H21C—C21A—H21D107.5
H17A—C17—H17B104.0 (11)C23A—C22A—C21A116.7 (5)
C17—C18—C19113.18 (8)C23A—C22A—H22B115.8 (9)
C17—C18—H18A109.7 (8)C21A—C22A—H22B110.4 (9)
C19—C18—H18A109.2 (8)C23A—C22A—H22C108.1
C17—C18—H18B110.7 (10)C21A—C22A—H22C108.1
C19—C18—H18B108.9 (10)C23A—C22A—H22D108.1
H18A—C18—H18B104.8 (13)C21A—C22A—H22D108.1
C20—C19—C18113.27 (9)H22C—C22A—H22D107.3
C20—C19—H19A112.0 (8)C24A—C23A—H23B112.0 (6)
C18—C19—H19A106.7 (8)C24A—C23A—H24A94.1 (8)
C20—C19—H19B111.1 (9)C24A—C23A—H24B45.9 (5)
C18—C19—H19B111.6 (9)C22A—C23A—H23C108.6
H19A—C19—H19B101.6 (11)C24A—C23A—H23C108.6
C21—C20—C19114.27 (8)C22A—C23A—H23D108.6
C21—C20—H20A110.5 (7)C24A—C23A—H23D108.6
C19—C20—H20A109.0 (7)H23C—C23A—H23D107.6
C21—C20—H20B107.2 (8)C13A—C24A—C23A115.7 (5)
C19—C20—H20B108.6 (8)C13A—C24A—H24C108.4
H20A—C20—H20B107.0 (11)C23A—C24A—H24C108.4
C20—C21—C22114.80 (7)C13A—C24A—H24D108.4
C20—C21—H21A107.6 (8)C23A—C24A—H24D108.4
C22—C21—H21A109.4 (8)H24C—C24A—H24D107.4
C20—C21—H21B108.1 (7)
O2—S1—N2—C13A62.8 (3)C2—C1—C10—C5−5.06 (8)
O1—S1—N2—C13A−168.5 (3)N1—C1—C10—C5177.07 (5)
C6—S1—N2—C13A−51.5 (3)C13A—N2—C13—C1442.4 (10)
O2—S1—N2—C1342.85 (6)S1—N2—C13—C14136.27 (6)
O1—S1—N2—C13171.52 (6)C13A—N2—C13—C24167.4 (11)
C6—S1—N2—C13−71.44 (6)S1—N2—C13—C24−98.73 (7)
C12—N1—C1—C2−14.76 (9)N2—C13—C14—C15−81.47 (9)
C11—N1—C1—C2112.73 (7)C24—C13—C14—C15155.60 (7)
C12—N1—C1—C10163.04 (6)C13—C14—C15—C16−64.30 (10)
C11—N1—C1—C10−69.47 (7)C14—C15—C16—C17−65.13 (10)
N1—C1—C2—C3−179.36 (6)C15—C16—C17—C18165.48 (8)
C10—C1—C2—C32.87 (9)C16—C17—C18—C19−72.80 (12)
C1—C2—C3—C40.86 (10)C17—C18—C19—C20−71.53 (13)
C2—C3—C4—C5−2.33 (10)C18—C19—C20—C21155.92 (8)
C3—C4—C5—C100.04 (9)C19—C20—C21—C22−64.74 (11)
C3—C4—C5—C6−178.96 (6)C20—C21—C22—C23−65.97 (11)
C4—C5—C6—C7175.23 (6)C21—C22—C23—C24165.03 (7)
C10—C5—C6—C7−3.79 (9)C22—C23—C24—C13−71.56 (10)
C4—C5—C6—S1−11.56 (8)N2—C13—C24—C23165.44 (7)
C10—C5—C6—S1169.42 (4)C14—C13—C24—C23−72.05 (9)
O2—S1—C6—C7−6.61 (6)C13—N2—C13A—C24A−32.4 (8)
O1—S1—C6—C7−137.25 (5)S1—N2—C13A—C24A−128.7 (4)
N2—S1—C6—C7108.23 (5)C13—N2—C13A—C14A−157.3 (15)
O2—S1—C6—C5179.88 (5)S1—N2—C13A—C14A106.4 (5)
O1—S1—C6—C549.24 (6)N2—C13A—C14A—C15A−166.6 (5)
N2—S1—C6—C5−65.28 (5)C24A—C13A—C14A—C15A73.3 (7)
C5—C6—C7—C8−0.35 (10)C13A—C14A—C15A—C16A66.8 (7)
S1—C6—C7—C8−173.85 (5)C14A—C15A—C16A—C17A−164.6 (5)
C6—C7—C8—C92.78 (10)C15A—C16A—C17A—C18A69.2 (8)
C7—C8—C9—C10−0.90 (10)C16A—C17A—C18A—C19A64.7 (8)
C8—C9—C10—C5−3.35 (9)C17A—C18A—C19A—C20A−153.6 (6)
C8—C9—C10—C1179.58 (6)C18A—C19A—C20A—C21A68.7 (8)
C4—C5—C10—C9−173.51 (6)C19A—C20A—C21A—C22A70.4 (7)
C6—C5—C10—C95.55 (8)C20A—C21A—C22A—C23A−163.5 (5)
C4—C5—C10—C13.62 (8)C21A—C22A—C23A—C24A67.6 (6)
C6—C5—C10—C1−177.32 (5)N2—C13A—C24A—C23A79.3 (6)
C2—C1—C10—C9172.01 (6)C14A—C13A—C24A—C23A−156.7 (5)
N1—C1—C10—C9−5.86 (8)C22A—C23A—C24A—C13A67.2 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.84 (1)2.28 (1)3.065 (1)154 (1)
C4—H4···O10.952.343.026 (1)128
C20—H20A···CgAii1.031 (12)2.88 (1)3.595 (1)126 (1)
C20—H20B···CgBii0.959 (14)2.84 (1)3.613 (1)140 (1)
C20A—H20D···CgBii0.992.813.792 (1)170
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC24H36N2O2S
Mr416.62
Crystal system, space groupMonoclinic, P21/c
Temperature (K)93
a, b, c (Å)10.3564 (3), 13.5117 (4), 16.2076 (4)
β (°) 95.814 (1)
V (Å3)2256.30 (11)
Z4
Radiation typeMo Kα
µ (mm−1)0.17
Crystal size (mm)0.54 × 0.42 × 0.29
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti scan
(SADABS; Sheldrick, 2002)
Tmin, Tmax0.826, 0.954
No. of measured, independent and
observed [I > 2σ(I)] reflections		71103, 14866, 10604
Rint0.034
(sin θ/λ)max (Å−1)0.924
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.120, 1.02
No. of reflections14866
No. of parameters469
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.46, −0.26

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.835 (12)2.28 (1)3.065 (1)154 (1)
C4—H4···O10.952.343.026 (1)128
C20—H20A···CgAii1.031 (12)2.88 (1)3.595 (1)126 (1)
C20—H20B···CgBii0.959 (14)2.84 (1)3.613 (1)140 (1)
C20A—H20D···CgBii0.992.813.792 (1)170
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1, y, z.
 

Acknowledgements

Financial support from the German Federal Ministry of Economics and Technolgy (BMWi) under grant No. 16IN0218 `ChemoChips' is gratefully acknowledged.

References

First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDunitz, J. D. & Shearer, H. M. M. (1960). Helv. Chim. Acta, 43, 18–35.  CSD CrossRef CAS Web of Science Google Scholar
 First citationFeiler, L., Langhals, H. & Polborn, K. (1995). Liebigs Ann. pp. 1229–1244.  CrossRef Google Scholar
 First citationGruber, T., Seichter, W. & Weber, E. (2008). Supramol. Chem. In the press.  Google Scholar
 First citationNishio, M. (2004). CrystEngComm, 6, 130–158.  Web of Science CrossRef CAS Google Scholar
 First citationRudert, R., Vollhardt, D. & Czichocki, G. (1994). Acta Cryst. C50, 1054–1057.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationSchönefeld, K., Barann, A., Vogel, K., Feller, K.-H., Kunze, D., Müller, P. & Weber, E. (2005). Int. J. Environ. Anal. Chem. 85, 655–663.  Google Scholar
 First citationSheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWeber, E., Kunze, D. & Seichter, W. (2004). Acta Cryst. E60, o2331–o2333.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 7| July 2008| Page o1204
doi:10.1107/S1600536808016164
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS