PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2867.
Published online 2009 October 28. doi:  10.1107/S1600536809044006
PMCID: PMC2971250

N-Cyclo­hexyl-N-ethyl­benzene­sulfonamide

Abstract

The title compound, C14H21NO2S, synthesized by N-methyl­ation of cyclo­hexyl­amine sulfonamide with ethyl iodide is of inter­est as a precursor to biologically active sulfur-containing heterocyclic compounds. There are two independent mol­ecules in the asymmetric unit. The dihedral angles between the mean planes of the phenyl ring and the cyclo­hexyl ring are 40.29 (11) and 37.91 (13)° in the two mol­ecules.

Related literature

For the synthesis of related mol­ecules, see: Arshad et al. (2009 [triangle]); Zia-ur-Rehman et al. (2009 [triangle]). For the biological activity of sulfonamides, see: Berredjem et al. (2000 [triangle]); Lee & Lee (2002 [triangle]); Soledade et al. (2006 [triangle]); Xiao & Timberlake (2000 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2867-scheme1.jpg

Experimental

Crystal data

  • C14H21NO2S
  • M r = 267.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2867-efi1.jpg
  • a = 18.195 (1) Å
  • b = 12.9799 (7) Å
  • c = 12.7327 (6) Å
  • β = 108.587 (3)°
  • V = 2850.2 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.22 mm−1
  • T = 296 K
  • 0.42 × 0.11 × 0.08 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: none
  • 32427 measured reflections
  • 7061 independent reflections
  • 3979 reflections with I > 2σ(I)
  • R int = 0.056

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.148
  • S = 0.99
  • 7061 reflections
  • 327 parameters
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]) and Mercury (Macrae et al., 2006 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]) and local programs.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809044006/bt5111sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044006/bt5111Isup2.hkl

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

Acknowledgments

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer.

supplementary crystallographic information

Comment

Sulfonamide is an important functionality found in a number of synthetic as well as natural compounds possessing versatile type of biological activities e.g., herbicidal, anti-malarial, anti-convulsant and anti-hypertensive (Soledade et al., 2006; Xiao & Timberlake, 2000; Berredjem et al., 2000; Lee & Lee, 2002) activities.

As a part of our ongoing research program regarding the synthesis of sulfur containing heterocyclic compounds (Arshad et al., 2009; Zia-ur-Rehman et al. 2009), we, herein report the crystal structure of the title compound (Scheme and figure1). Bond lengths and bond angles are within the normal ranges. No significant hydrogen bond interactions are observed in the title molecule. The dihedral angles between the mean planes of the phenyl ring and the cyclohexyl ring are 40.29 (11)° and 37.91 (13)°, respectively, for the two molecules in the asymmetric unit.

Experimental

A mixture of N-cyclohexylbenzene sulfonamide1(g, 0.43 mmol), sodium hydride (0.21 g; 0.88 mmoles) and N, N-dimethylformamide (10.0 ml) was stirred at room temperature for half an hour followed by addition of ethyl iodide (0.134 g; 0.86 mmoles). Stirring was continued further for a period of three hours and the contents were poured over crushed ice. The precipitated product was isolated, washed and crystallized from a methanol-water mixture (50: 50).

Refinement

All hydrogen atoms were identified in the difference map. However, they were fixed in ideal positions and treated as riding on their parent atoms. The following distances were used: Cmethyl—H = 0.98Å; Caromatic—H = 0.95Å. U(H) was set to 1.2Ueq(C) or 1.5Ueq(Cmethyl).

Figures

Fig. 1.
The molecular structure of the title compound, with displacement ellipsoids at the 50% probability level. H atoms have been omitted for clarity.

Crystal data

C14H21NO2SF(000) = 1152
Mr = 267.38Dx = 1.246 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3394 reflections
a = 18.195 (1) Åθ = 2.3–21.8°
b = 12.9799 (7) ŵ = 0.22 mm1
c = 12.7327 (6) ÅT = 296 K
β = 108.587 (3)°Needles, colourless
V = 2850.2 (3) Å30.42 × 0.11 × 0.08 mm
Z = 8

Data collection

Bruker APEXII CCD area-detector diffractometer3979 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.056
graphiteθmax = 28.3°, θmin = 1.2°
[var phi] and ω scansh = −24→23
32427 measured reflectionsk = −17→16
7061 independent reflectionsl = −16→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.0572P)2 + 0.5289P] where P = (Fo2 + 2Fc2)/3
7061 reflections(Δ/σ)max < 0.001
327 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = −0.24 e Å3

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
S10.36993 (4)0.68047 (5)0.03599 (5)0.0533 (2)
O10.39686 (11)0.64718 (16)−0.05209 (14)0.0755 (6)
O20.37154 (11)0.78735 (14)0.06200 (17)0.0710 (6)
N10.28139 (11)0.64066 (15)0.00768 (15)0.0464 (5)
C10.42614 (14)0.61647 (19)0.1568 (2)0.0473 (6)
C20.46699 (15)0.5285 (2)0.1493 (2)0.0574 (7)
H20.46520.50290.08030.069*
C30.51032 (18)0.4790 (2)0.2447 (3)0.0751 (9)
H30.53810.42000.24010.090*
C40.5126 (2)0.5163 (3)0.3462 (3)0.0848 (11)
H40.54200.48260.41030.102*
C50.47221 (19)0.6025 (3)0.3537 (2)0.0793 (10)
H50.47370.62700.42300.095*
C60.42914 (16)0.6539 (2)0.2599 (2)0.0614 (7)
H60.40220.71330.26570.074*
C70.23333 (13)0.68049 (18)0.07358 (17)0.0409 (6)
H70.26140.73890.11670.049*
C80.15687 (14)0.7218 (2)−0.00157 (19)0.0529 (7)
H8A0.12760.6663−0.04700.063*
H8B0.16660.7735−0.05050.063*
C90.10942 (16)0.7692 (2)0.0651 (2)0.0637 (8)
H9A0.13570.83020.10290.076*
H9B0.05930.79020.01510.076*
C100.09773 (17)0.6946 (2)0.1492 (2)0.0725 (9)
H10A0.07140.72940.19440.087*
H10B0.06500.63830.11100.087*
C110.17359 (17)0.6522 (2)0.2226 (2)0.0701 (8)
H11A0.16370.60110.27190.084*
H11B0.20360.70740.26770.084*
C120.22025 (15)0.6035 (2)0.1559 (2)0.0572 (7)
H12A0.19280.54390.11640.069*
H12B0.26990.58050.20560.069*
C130.26176 (16)0.5405 (2)−0.0484 (2)0.0591 (7)
H13A0.22570.5049−0.01910.071*
H13B0.30840.4990−0.03170.071*
C140.2265 (2)0.5491 (3)−0.1719 (2)0.0908 (11)
H14A0.18210.5936−0.18920.136*
H14B0.21090.4821−0.20280.136*
H14C0.26400.5773−0.20260.136*
S20.14463 (4)0.28954 (5)0.47894 (6)0.0536 (2)
O30.12606 (12)0.31641 (16)0.57629 (15)0.0769 (6)
O40.13794 (11)0.18488 (13)0.44305 (17)0.0707 (6)
N20.23252 (11)0.32654 (14)0.49770 (15)0.0455 (5)
C150.08332 (14)0.36211 (19)0.3684 (2)0.0501 (6)
C160.07673 (16)0.3370 (2)0.2607 (2)0.0635 (8)
H160.10300.28030.24560.076*
C170.03073 (18)0.3967 (3)0.1753 (3)0.0799 (9)
H170.02670.38090.10240.096*
C18−0.00889 (18)0.4787 (3)0.1970 (3)0.0850 (10)
H18−0.04050.51810.13910.102*
C19−0.00210 (19)0.5031 (3)0.3045 (3)0.0829 (10)
H19−0.02910.55920.31920.099*
C200.04401 (17)0.4456 (2)0.3902 (3)0.0670 (8)
H200.04880.46280.46300.080*
C210.27320 (13)0.29122 (17)0.42041 (17)0.0398 (6)
H210.23840.24270.36900.048*
C220.29029 (15)0.37719 (19)0.35061 (19)0.0498 (6)
H22A0.24250.41230.31080.060*
H22B0.32500.42690.39850.060*
C230.32733 (15)0.3341 (2)0.26870 (19)0.0547 (7)
H23A0.29020.29050.21570.066*
H23B0.34080.39040.22820.066*
C240.39939 (15)0.2723 (2)0.3260 (2)0.0601 (7)
H24A0.41850.24080.27060.072*
H24B0.43930.31810.37050.072*
C250.38391 (16)0.1893 (2)0.3992 (2)0.0574 (7)
H25A0.43240.15610.43980.069*
H25B0.35010.13750.35330.069*
C260.34638 (14)0.23229 (19)0.48063 (19)0.0489 (6)
H26A0.33380.17620.52230.059*
H26B0.38260.27770.53250.059*
C270.26849 (18)0.4076 (2)0.5788 (2)0.0659 (8)
H27A0.32430.40320.59600.079*
H27B0.25670.39360.64660.079*
C280.2440 (2)0.5137 (2)0.5434 (3)0.0844 (10)
H28A0.25260.52750.47420.127*
H28B0.27360.56130.59850.127*
H28C0.18990.52150.53460.127*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0519 (4)0.0526 (4)0.0639 (4)0.0001 (3)0.0304 (3)0.0080 (3)
O10.0719 (14)0.1040 (16)0.0669 (12)0.0096 (12)0.0452 (10)0.0145 (11)
O20.0605 (13)0.0438 (11)0.1111 (15)−0.0072 (10)0.0307 (11)0.0086 (10)
N10.0459 (13)0.0466 (13)0.0501 (11)−0.0015 (10)0.0200 (9)−0.0048 (9)
C10.0412 (15)0.0473 (16)0.0577 (15)−0.0071 (13)0.0218 (12)−0.0012 (12)
C20.0539 (18)0.0514 (17)0.0708 (18)−0.0053 (15)0.0256 (15)0.0023 (14)
C30.059 (2)0.062 (2)0.106 (3)0.0033 (16)0.0268 (18)0.0164 (19)
C40.064 (2)0.096 (3)0.082 (2)−0.021 (2)0.0061 (18)0.029 (2)
C50.072 (2)0.099 (3)0.0605 (19)−0.024 (2)0.0135 (17)0.0000 (19)
C60.0545 (18)0.0647 (19)0.0678 (18)−0.0144 (15)0.0236 (15)−0.0111 (15)
C70.0436 (14)0.0394 (14)0.0427 (12)−0.0033 (11)0.0179 (11)−0.0017 (10)
C80.0531 (16)0.0558 (17)0.0501 (13)0.0040 (14)0.0168 (12)0.0076 (12)
C90.0546 (18)0.070 (2)0.0715 (17)0.0138 (15)0.0270 (14)0.0101 (15)
C100.061 (2)0.086 (2)0.084 (2)0.0137 (17)0.0427 (16)0.0132 (17)
C110.081 (2)0.079 (2)0.0640 (17)0.0060 (18)0.0433 (16)0.0147 (15)
C120.0603 (18)0.0580 (17)0.0589 (15)0.0040 (15)0.0268 (13)0.0149 (13)
C130.0666 (19)0.0513 (17)0.0613 (16)0.0017 (14)0.0228 (14)−0.0094 (13)
C140.109 (3)0.096 (3)0.0632 (19)0.005 (2)0.0218 (18)−0.0250 (18)
S20.0558 (4)0.0487 (4)0.0696 (4)−0.0011 (3)0.0386 (3)0.0054 (3)
O30.0871 (15)0.0920 (15)0.0755 (12)0.0103 (12)0.0596 (11)0.0152 (11)
O40.0642 (13)0.0413 (11)0.1158 (15)−0.0094 (10)0.0415 (11)0.0017 (10)
N20.0521 (13)0.0427 (12)0.0492 (11)−0.0066 (10)0.0267 (9)−0.0077 (9)
C150.0408 (15)0.0497 (16)0.0676 (16)−0.0033 (13)0.0283 (13)−0.0019 (13)
C160.0528 (18)0.069 (2)0.0711 (18)−0.0079 (16)0.0239 (15)−0.0120 (16)
C170.051 (2)0.109 (3)0.071 (2)−0.010 (2)0.0067 (16)0.004 (2)
C180.047 (2)0.083 (3)0.112 (3)−0.0060 (19)0.0077 (19)0.027 (2)
C190.061 (2)0.067 (2)0.121 (3)0.0084 (18)0.029 (2)0.000 (2)
C200.0582 (19)0.066 (2)0.083 (2)0.0117 (16)0.0302 (16)−0.0007 (17)
C210.0427 (14)0.0390 (13)0.0422 (12)−0.0044 (11)0.0197 (10)−0.0044 (10)
C220.0575 (17)0.0498 (15)0.0476 (13)0.0004 (13)0.0245 (12)0.0043 (12)
C230.0635 (18)0.0614 (18)0.0476 (13)0.0016 (15)0.0297 (13)0.0063 (12)
C240.0572 (18)0.0721 (19)0.0619 (15)0.0006 (15)0.0344 (13)0.0032 (14)
C250.0535 (17)0.0617 (18)0.0647 (15)0.0106 (14)0.0298 (13)0.0053 (14)
C260.0500 (16)0.0511 (16)0.0496 (13)0.0011 (13)0.0217 (12)0.0058 (12)
C270.085 (2)0.0609 (19)0.0617 (16)−0.0021 (17)0.0371 (15)−0.0122 (15)
C280.115 (3)0.060 (2)0.085 (2)0.0096 (19)0.041 (2)−0.0057 (17)

Geometric parameters (Å, °)

S1—O21.4244 (19)S2—O41.4261 (18)
S1—O11.4266 (18)S2—O31.4280 (17)
S1—N11.619 (2)S2—N21.613 (2)
S1—C11.761 (3)S2—C151.764 (3)
N1—C131.472 (3)N2—C271.473 (3)
N1—C71.485 (3)N2—C211.480 (3)
C1—C21.382 (3)C15—C201.375 (4)
C1—C61.384 (3)C15—C161.377 (3)
C2—C31.378 (4)C16—C171.379 (4)
C2—H20.9300C16—H160.9300
C3—C41.368 (4)C17—C181.363 (5)
C3—H30.9300C17—H170.9300
C4—C51.359 (5)C18—C191.371 (5)
C4—H40.9300C18—H180.9300
C5—C61.374 (4)C19—C201.367 (4)
C5—H50.9300C19—H190.9300
C6—H60.9300C20—H200.9300
C7—C81.513 (3)C21—C261.515 (3)
C7—C121.520 (3)C21—C221.519 (3)
C7—H70.9800C21—H210.9800
C8—C91.520 (3)C22—C231.517 (3)
C8—H8A0.9700C22—H22A0.9700
C8—H8B0.9700C22—H22B0.9700
C9—C101.508 (4)C23—C241.512 (4)
C9—H9A0.9700C23—H23A0.9700
C9—H9B0.9700C23—H23B0.9700
C10—C111.503 (4)C24—C251.508 (3)
C10—H10A0.9700C24—H24A0.9700
C10—H10B0.9700C24—H24B0.9700
C11—C121.517 (3)C25—C261.519 (3)
C11—H11A0.9700C25—H25A0.9700
C11—H11B0.9700C25—H25B0.9700
C12—H12A0.9700C26—H26A0.9700
C12—H12B0.9700C26—H26B0.9700
C13—C141.501 (4)C27—C281.474 (4)
C13—H13A0.9700C27—H27A0.9700
C13—H13B0.9700C27—H27B0.9700
C14—H14A0.9600C28—H28A0.9600
C14—H14B0.9600C28—H28B0.9600
C14—H14C0.9600C28—H28C0.9600
O2—S1—O1119.41 (12)O4—S2—O3119.41 (12)
O2—S1—N1107.93 (11)O4—S2—N2108.09 (11)
O1—S1—N1107.15 (11)O3—S2—N2107.24 (11)
O2—S1—C1107.05 (12)O4—S2—C15106.58 (12)
O1—S1—C1107.14 (12)O3—S2—C15107.33 (12)
N1—S1—C1107.67 (11)N2—S2—C15107.70 (11)
C13—N1—C7119.10 (19)C27—N2—C21118.87 (19)
C13—N1—S1117.41 (17)C27—N2—S2120.95 (16)
C7—N1—S1119.11 (15)C21—N2—S2119.45 (15)
C2—C1—C6119.8 (2)C20—C15—C16120.2 (3)
C2—C1—S1120.3 (2)C20—C15—S2119.8 (2)
C6—C1—S1120.0 (2)C16—C15—S2120.0 (2)
C3—C2—C1119.5 (3)C15—C16—C17119.4 (3)
C3—C2—H2120.3C15—C16—H16120.3
C1—C2—H2120.3C17—C16—H16120.3
C4—C3—C2120.3 (3)C18—C17—C16120.4 (3)
C4—C3—H3119.8C18—C17—H17119.8
C2—C3—H3119.8C16—C17—H17119.8
C5—C4—C3120.2 (3)C17—C18—C19119.9 (3)
C5—C4—H4119.9C17—C18—H18120.1
C3—C4—H4119.9C19—C18—H18120.1
C4—C5—C6120.7 (3)C20—C19—C18120.5 (3)
C4—C5—H5119.7C20—C19—H19119.7
C6—C5—H5119.7C18—C19—H19119.7
C5—C6—C1119.5 (3)C19—C20—C15119.7 (3)
C5—C6—H6120.2C19—C20—H20120.2
C1—C6—H6120.2C15—C20—H20120.2
N1—C7—C8110.77 (18)N2—C21—C26111.41 (18)
N1—C7—C12114.24 (19)N2—C21—C22113.61 (19)
C8—C7—C12110.8 (2)C26—C21—C22110.87 (19)
N1—C7—H7106.9N2—C21—H21106.8
C8—C7—H7106.9C26—C21—H21106.8
C12—C7—H7106.9C22—C21—H21106.8
C7—C8—C9111.2 (2)C23—C22—C21110.5 (2)
C7—C8—H8A109.4C23—C22—H22A109.6
C9—C8—H8A109.4C21—C22—H22A109.6
C7—C8—H8B109.4C23—C22—H22B109.6
C9—C8—H8B109.4C21—C22—H22B109.6
H8A—C8—H8B108.0H22A—C22—H22B108.1
C10—C9—C8111.7 (2)C24—C23—C22111.8 (2)
C10—C9—H9A109.3C24—C23—H23A109.3
C8—C9—H9A109.3C22—C23—H23A109.3
C10—C9—H9B109.3C24—C23—H23B109.3
C8—C9—H9B109.3C22—C23—H23B109.3
H9A—C9—H9B107.9H23A—C23—H23B107.9
C11—C10—C9111.5 (2)C25—C24—C23111.9 (2)
C11—C10—H10A109.3C25—C24—H24A109.2
C9—C10—H10A109.3C23—C24—H24A109.2
C11—C10—H10B109.3C25—C24—H24B109.2
C9—C10—H10B109.3C23—C24—H24B109.2
H10A—C10—H10B108.0H24A—C24—H24B107.9
C10—C11—C12111.8 (2)C24—C25—C26111.9 (2)
C10—C11—H11A109.3C24—C25—H25A109.2
C12—C11—H11A109.3C26—C25—H25A109.2
C10—C11—H11B109.3C24—C25—H25B109.2
C12—C11—H11B109.3C26—C25—H25B109.2
H11A—C11—H11B107.9H25A—C25—H25B107.9
C11—C12—C7110.5 (2)C21—C26—C25110.73 (19)
C11—C12—H12A109.5C21—C26—H26A109.5
C7—C12—H12A109.5C25—C26—H26A109.5
C11—C12—H12B109.5C21—C26—H26B109.5
C7—C12—H12B109.5C25—C26—H26B109.5
H12A—C12—H12B108.1H26A—C26—H26B108.1
N1—C13—C14113.5 (2)N2—C27—C28115.4 (2)
N1—C13—H13A108.9N2—C27—H27A108.4
C14—C13—H13A108.9C28—C27—H27A108.4
N1—C13—H13B108.9N2—C27—H27B108.4
C14—C13—H13B108.9C28—C27—H27B108.4
H13A—C13—H13B107.7H27A—C27—H27B107.5
C13—C14—H14A109.5C27—C28—H28A109.5
C13—C14—H14B109.5C27—C28—H28B109.5
H14A—C14—H14B109.5H28A—C28—H28B109.5
C13—C14—H14C109.5C27—C28—H28C109.5
H14A—C14—H14C109.5H28A—C28—H28C109.5
H14B—C14—H14C109.5H28B—C28—H28C109.5
O2—S1—N1—C13164.91 (17)O4—S2—N2—C27−151.80 (18)
O1—S1—N1—C1335.1 (2)O3—S2—N2—C27−21.8 (2)
C1—S1—N1—C13−79.84 (19)C15—S2—N2—C2793.4 (2)
O2—S1—N1—C7−38.8 (2)O4—S2—N2—C2138.1 (2)
O1—S1—N1—C7−168.55 (16)O3—S2—N2—C21168.11 (17)
C1—S1—N1—C776.49 (19)C15—S2—N2—C21−76.65 (19)
O2—S1—C1—C2−148.1 (2)O4—S2—C15—C20144.5 (2)
O1—S1—C1—C2−18.9 (2)O3—S2—C15—C2015.5 (2)
N1—S1—C1—C296.0 (2)N2—S2—C15—C20−99.7 (2)
O2—S1—C1—C632.3 (2)O4—S2—C15—C16−37.5 (2)
O1—S1—C1—C6161.5 (2)O3—S2—C15—C16−166.5 (2)
N1—S1—C1—C6−83.5 (2)N2—S2—C15—C1678.3 (2)
C6—C1—C2—C30.0 (4)C20—C15—C16—C170.4 (4)
S1—C1—C2—C3−179.6 (2)S2—C15—C16—C17−177.7 (2)
C1—C2—C3—C40.4 (4)C15—C16—C17—C18−1.1 (4)
C2—C3—C4—C50.0 (5)C16—C17—C18—C191.0 (5)
C3—C4—C5—C6−0.6 (5)C17—C18—C19—C20−0.2 (5)
C4—C5—C6—C10.9 (4)C18—C19—C20—C15−0.6 (5)
C2—C1—C6—C5−0.6 (4)C16—C15—C20—C190.5 (4)
S1—C1—C6—C5179.0 (2)S2—C15—C20—C19178.5 (2)
C13—N1—C7—C8−76.0 (3)C27—N2—C21—C2668.9 (3)
S1—N1—C7—C8128.08 (19)S2—N2—C21—C26−120.80 (19)
C13—N1—C7—C1249.9 (3)C27—N2—C21—C22−57.1 (3)
S1—N1—C7—C12−106.0 (2)S2—N2—C21—C22113.1 (2)
N1—C7—C8—C9−176.3 (2)N2—C21—C22—C23−176.43 (19)
C12—C7—C8—C955.9 (3)C26—C21—C22—C2357.2 (3)
C7—C8—C9—C10−54.6 (3)C21—C22—C23—C24−55.4 (3)
C8—C9—C10—C1153.9 (3)C22—C23—C24—C2553.6 (3)
C9—C10—C11—C12−54.9 (3)C23—C24—C25—C26−53.3 (3)
C10—C11—C12—C756.1 (3)N2—C21—C26—C25175.45 (19)
N1—C7—C12—C11177.6 (2)C22—C21—C26—C25−57.0 (3)
C8—C7—C12—C11−56.5 (3)C24—C25—C26—C2155.0 (3)
C7—N1—C13—C14107.4 (3)C21—N2—C27—C2893.3 (3)
S1—N1—C13—C14−96.2 (3)S2—N2—C27—C28−76.8 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5111).

References

  • Arshad, M. N., Zia-ur-Rehman, M. & Khan, I. U. (2009). Acta Cryst. E65, o2596. [PMC free article] [PubMed]
  • Berredjem, M., Régainia, Z., Djahoudi, A., Aouf, N. E., Dewinter, G. & Montero, J. L. (2000). Phosphorus Sulfur Silicon Relat. Elem 165, 249–264.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Lee, J. S. & Lee, C. H. (2002). Bull. Korean Chem. Soc.23, 167–169.
  • Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst.39, 453–457.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Soledade, M., Pedras, C. & Jha, M. (2006). Bioorg. Med. Chem 14, 4958–4979. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Xiao, Z. & Timberlake, J. W. (2000). J. Heterocycl. Chem 37, 773–777.
  • Zia-ur-Rehman, M., Choudary, J. A., Elsegood, M. R. J., Siddiqui, H. L. & Khan, K. M. (2009). Eur. J. Med. Chem 44, 1311–1316. [PubMed]

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