PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1509.
Published online 2010 May 29. doi:  10.1107/S1600536810019690
PMCID: PMC2979489

Diethyl 2-{[3-(2,4,6-trimethyl­benz­yl)-1-phenyl­sulfonyl-1H-indol-2-yl]methyl­idene}propane­dioate

Abstract

In the title compound, C32H33NO6S, the indole ring system makes dihedral angles of 62.78 (10) and 80.53 (8)°, respectively, with the phenyl and benzene rings. In the crystal, the mol­ecules are linked through inter­molecular C—H(...)O hydrogen bonds, forming a chain along the a axis. Between the chains, a weak aromatic π–π stacking inter­action [centroid–centroid distance = 3.831 (2) Å] is observed.

Related literature

For the biological activity of indole derivatives, see: Ma et al. (2001 [triangle]); Zhao et al. (2002 [triangle]); Zhou et al. (2006 [triangle]). For related structures, see: Chakkaravarthi et al. (2007 [triangle], 2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1509-scheme1.jpg

Experimental

Crystal data

  • C32H33NO6S
  • M r = 559.65
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1509-efi1.jpg
  • a = 8.5103 (4) Å
  • b = 8.9540 (4) Å
  • c = 19.6546 (10) Å
  • α = 78.456 (3)°
  • β = 87.236 (4)°
  • γ = 86.736 (3)°
  • V = 1463.99 (12) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.16 mm−1
  • T = 295 K
  • 0.22 × 0.18 × 0.16 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.967, T max = 0.976
  • 26660 measured reflections
  • 7349 independent reflections
  • 4328 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.211
  • S = 1.03
  • 7349 reflections
  • 370 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.42 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019690/is2550sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019690/is2550Isup2.hkl

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

Acknowledgments

The authors wish to acknowledge DV University of Madras for the data collection.

supplementary crystallographic information

Comment

Indole derivatives are found to possess anticancer, antimalarial and antihypertensive activities (Ma et al., 2001; Zhou et al., 2006; Zhao et al., 2002). In continuation of our studies in indole derivatives, we report the crystal structure of the title compound, (I). The geometric parameters of (I) (Fig. 1) agree with those in the reported structures (Chakkaravarthi et al., 2007, 2008).

The nine-membered indole ring system forms dihedral angles of 62.78 (10) and 80.53 (8)° with the phenyl ring (C1–C6) and benzene ring (C24–C29), respectively. The torsion angles O2—S1—N1—C7 and O1—S1—N1—C14 [-37.8 (2)° and 62.87 (18)°, respectively] indicate the syn-conformation of the sulfonyl moiety. The sum of the bond angles around N1 [342.1 (2)°] indicates that N1 is sp3-hybridized.

The molecular structure is stabilized by a weak intramolecular C—H···O interaction and the crystal packing of (I) (Fig. 2) exhibits weak intermolecular C—H···O (Table 1) and π–π interactions [Cg···Cg (-x, -y, 1-z) distance of 3.831 (2) Å]; Cg is the centroid of the C1–C6 ring.

Experimental

To a solution of diethyl-2-((3-(bromomethyl)-1-(phenylsulfonyl) -1H-indol-2-yl)methylene)malonate (0.3 g, 0.57 mmol) in dry 1,2-dichloroethane (15 ml), anhydrous ZnBr2 (0.25 g, 1.11 mmol) and mesitylene (0.19 ml, 1.41 mmol) were added. It was then refluxed for 4 h under N2 atmosphere. The solvent was removed and the residue was quenched with ice-water (50 ml) containing 1 ml of conc. HCl, extracted with chloroform (2 × 10 ml) and dried (Na2SO4). Removal of solvent followed by flash column chromatographic purification (n-hexane/ethyl acetate 98:2) led to the isolation of product as a colourless crystal.

Refinement

H atom attached to C15 was located from a difference Fourier map and refined freely. All other H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for methylene, and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl. C21—C22 and C18—C19 distances were restrained to 1.550 (7) Å.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The packing of (I), viewed down the c axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C32H33NO6SZ = 2
Mr = 559.65F(000) = 592
Triclinic, P1Dx = 1.270 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.5103 (4) ÅCell parameters from 7772 reflections
b = 8.9540 (4) Åθ = 2.4–24.3°
c = 19.6546 (10) ŵ = 0.16 mm1
α = 78.456 (3)°T = 295 K
β = 87.236 (4)°Block, colourless
γ = 86.736 (3)°0.22 × 0.18 × 0.16 mm
V = 1463.99 (12) Å3

Data collection

Bruker Kappa APEXII diffractometer7349 independent reflections
Radiation source: fine-focus sealed tube4328 reflections with I > 2σ(I)
graphiteRint = 0.042
ω and [var phi] scansθmax = 28.5°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→10
Tmin = 0.967, Tmax = 0.976k = −11→11
26660 measured reflectionsl = −26→22

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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.211H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.105P)2 + 0.4069P] where P = (Fo2 + 2Fc2)/3
7349 reflections(Δ/σ)max < 0.001
370 parametersΔρmax = 0.42 e Å3
2 restraintsΔρmin = −0.31 e Å3

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

xyzUiso*/Ueq
S1−0.00108 (7)0.35985 (9)0.37321 (3)0.0626 (2)
O1−0.0678 (2)0.4651 (3)0.41334 (11)0.0837 (6)
O2−0.0971 (2)0.2939 (3)0.33112 (10)0.0790 (6)
O3−0.0750 (3)0.2569 (3)0.11855 (14)0.1099 (9)
O4−0.1997 (3)0.6190 (3)0.21742 (15)0.1050 (8)
O5−0.1945 (3)0.4863 (3)0.08992 (14)0.1139 (9)
O60.0438 (3)0.6904 (2)0.18672 (12)0.0852 (6)
N10.1367 (2)0.4543 (2)0.31990 (10)0.0526 (5)
C10.1061 (3)0.2144 (3)0.42788 (13)0.0598 (6)
C20.1303 (4)0.2243 (4)0.49532 (16)0.0859 (9)
H20.09090.30890.51260.103*
C30.2130 (5)0.1083 (5)0.5370 (2)0.1025 (12)
H30.22740.11340.58310.123*
C40.2739 (5)−0.0135 (5)0.5118 (2)0.1069 (13)
H40.3293−0.09190.54060.128*
C50.2542 (6)−0.0217 (4)0.4438 (3)0.1226 (16)
H50.2988−0.10400.42610.147*
C60.1677 (5)0.0930 (3)0.40152 (18)0.0889 (10)
H60.15180.08730.35560.107*
C70.2050 (3)0.3920 (3)0.26267 (12)0.0489 (5)
C80.3634 (3)0.4001 (2)0.26078 (12)0.0487 (5)
C90.4031 (3)0.4704 (2)0.31715 (12)0.0490 (5)
C100.5466 (3)0.5094 (3)0.33863 (15)0.0623 (6)
H100.64030.49020.31480.075*
C110.5468 (4)0.5764 (3)0.39536 (16)0.0722 (8)
H110.64160.60320.41020.087*
C120.4072 (4)0.6049 (3)0.43112 (16)0.0721 (8)
H120.41060.64890.47000.087*
C130.2652 (3)0.5699 (3)0.41068 (14)0.0653 (7)
H130.17210.59060.43460.078*
C140.2644 (3)0.5025 (3)0.35296 (12)0.0503 (5)
C150.1071 (3)0.3562 (3)0.20960 (13)0.0563 (6)
C16−0.0135 (3)0.4425 (3)0.18005 (13)0.0592 (6)
C17−0.0687 (4)0.5916 (3)0.19722 (14)0.0671 (7)
C180.0018 (6)0.8430 (4)0.1979 (2)0.1203 (15)
H19A−0.10970.86550.19040.144*
H19B0.06000.91630.16440.144*
C190.0364 (8)0.8585 (6)0.2684 (3)0.161 (2)
H66A−0.02920.79350.30140.241*
H66B0.01590.96260.27300.241*
H66C0.14510.82940.27690.241*
C20−0.1044 (4)0.4002 (4)0.12446 (16)0.0763 (8)
C21−0.1577 (6)0.2046 (7)0.0635 (2)0.1310 (17)
H21A−0.18740.09990.07920.157*
H21B−0.25200.26850.05120.157*
C22−0.0463 (8)0.2163 (10)0.0041 (3)0.191 (3)
H33A0.05570.17690.01980.287*
H33B−0.04020.3214−0.01850.287*
H33C−0.08120.1584−0.02800.287*
C230.4831 (3)0.3629 (3)0.20674 (15)0.0629 (7)
H23A0.58700.36020.22530.076*
H23B0.47850.44560.16650.076*
C240.4654 (3)0.2139 (3)0.18243 (12)0.0514 (5)
C250.4139 (3)0.2122 (3)0.11623 (12)0.0545 (6)
C260.4067 (3)0.0728 (3)0.09579 (14)0.0637 (7)
H260.37160.07190.05180.076*
C270.4493 (3)−0.0634 (3)0.13816 (16)0.0683 (7)
C280.5004 (4)−0.0589 (3)0.20301 (16)0.0722 (8)
H280.5302−0.15000.23240.087*
C290.5091 (3)0.0768 (3)0.22612 (13)0.0606 (6)
C300.3701 (4)0.3567 (3)0.06561 (15)0.0847 (9)
H30A0.46120.41660.05380.127*
H30B0.28940.41420.08650.127*
H30C0.33190.33150.02440.127*
C310.4440 (5)−0.2144 (4)0.1150 (2)0.1061 (13)
H31A0.5475−0.26320.11640.159*
H31B0.4078−0.19700.06850.159*
H31C0.3732−0.27890.14560.159*
C320.5710 (5)0.0727 (5)0.29715 (17)0.0964 (11)
H32A0.5875−0.03140.32070.145*
H32B0.49600.12440.32360.145*
H32C0.66900.12270.29240.145*
H150.143 (4)0.268 (4)0.1932 (16)0.085 (9)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0375 (3)0.0952 (5)0.0569 (4)0.0061 (3)−0.0024 (3)−0.0216 (3)
O10.0545 (11)0.1244 (17)0.0742 (13)0.0296 (11)0.0046 (9)−0.0356 (12)
O20.0433 (10)0.1292 (17)0.0664 (11)−0.0156 (10)−0.0065 (8)−0.0196 (12)
O30.116 (2)0.123 (2)0.1081 (18)0.0088 (16)−0.0507 (16)−0.0572 (16)
O40.0776 (16)0.0955 (16)0.132 (2)0.0165 (13)0.0206 (15)−0.0106 (15)
O50.114 (2)0.134 (2)0.0925 (17)0.0064 (17)−0.0521 (16)−0.0129 (16)
O60.0803 (14)0.0767 (13)0.1012 (16)−0.0048 (11)−0.0096 (12)−0.0222 (12)
N10.0419 (10)0.0665 (12)0.0531 (11)0.0079 (9)−0.0069 (8)−0.0224 (9)
C10.0464 (13)0.0751 (16)0.0592 (14)−0.0097 (12)−0.0018 (11)−0.0144 (12)
C20.082 (2)0.112 (2)0.0647 (18)0.0148 (19)−0.0113 (16)−0.0244 (18)
C30.100 (3)0.126 (3)0.076 (2)0.005 (2)−0.025 (2)−0.003 (2)
C40.112 (3)0.079 (2)0.117 (3)−0.005 (2)−0.026 (3)0.016 (2)
C50.171 (5)0.0572 (19)0.136 (4)0.013 (2)−0.016 (3)−0.014 (2)
C60.126 (3)0.0638 (17)0.080 (2)−0.0078 (18)−0.013 (2)−0.0185 (16)
C70.0446 (12)0.0520 (12)0.0521 (12)0.0033 (9)−0.0016 (10)−0.0168 (10)
C80.0460 (12)0.0451 (11)0.0557 (13)0.0033 (9)−0.0004 (10)−0.0132 (10)
C90.0453 (12)0.0443 (11)0.0578 (13)0.0030 (9)−0.0075 (10)−0.0111 (10)
C100.0492 (14)0.0630 (15)0.0762 (17)−0.0023 (11)−0.0088 (12)−0.0160 (13)
C110.0664 (18)0.0683 (16)0.087 (2)−0.0012 (13)−0.0280 (15)−0.0228 (15)
C120.081 (2)0.0662 (16)0.0774 (18)0.0166 (14)−0.0329 (16)−0.0323 (14)
C130.0630 (16)0.0722 (16)0.0663 (16)0.0201 (13)−0.0149 (13)−0.0305 (13)
C140.0471 (12)0.0492 (12)0.0571 (13)0.0112 (10)−0.0116 (10)−0.0175 (10)
C150.0494 (13)0.0685 (15)0.0556 (14)−0.0023 (11)0.0002 (11)−0.0243 (12)
C160.0516 (14)0.0766 (16)0.0496 (13)−0.0056 (12)−0.0022 (11)−0.0121 (12)
C170.0627 (17)0.0747 (17)0.0579 (15)0.0066 (14)−0.0037 (13)−0.0016 (13)
C180.129 (4)0.080 (2)0.152 (4)0.010 (2)−0.020 (3)−0.025 (3)
C190.221 (7)0.123 (4)0.158 (5)0.045 (4)−0.067 (5)−0.075 (3)
C200.0659 (18)0.100 (2)0.0638 (17)−0.0061 (16)−0.0127 (14)−0.0151 (16)
C210.119 (4)0.178 (5)0.116 (3)−0.015 (3)−0.037 (3)−0.069 (3)
C220.170 (6)0.307 (9)0.127 (4)−0.039 (6)−0.001 (4)−0.109 (6)
C230.0544 (14)0.0630 (14)0.0751 (17)−0.0084 (12)0.0160 (12)−0.0250 (13)
C240.0454 (12)0.0514 (12)0.0561 (13)0.0037 (10)0.0065 (10)−0.0116 (10)
C250.0534 (13)0.0565 (13)0.0496 (13)0.0071 (10)0.0074 (10)−0.0058 (10)
C260.0599 (15)0.0753 (17)0.0586 (15)0.0010 (13)0.0005 (12)−0.0217 (13)
C270.0668 (17)0.0553 (14)0.0840 (19)0.0031 (12)0.0043 (14)−0.0204 (14)
C280.0753 (19)0.0520 (14)0.082 (2)0.0174 (13)−0.0007 (15)−0.0013 (13)
C290.0551 (14)0.0650 (15)0.0589 (15)0.0131 (12)−0.0055 (11)−0.0092 (12)
C300.106 (3)0.0739 (18)0.0615 (17)0.0176 (17)0.0107 (16)0.0080 (14)
C310.113 (3)0.0680 (19)0.146 (3)−0.0031 (19)0.008 (3)−0.046 (2)
C320.096 (3)0.117 (3)0.074 (2)0.029 (2)−0.0270 (18)−0.0164 (19)

Geometric parameters (Å, °)

S1—O21.420 (2)C15—H150.94 (3)
S1—O11.424 (2)C16—C171.487 (4)
S1—N11.682 (2)C16—C201.488 (4)
S1—C11.755 (3)C18—C191.465 (5)
O3—C201.320 (4)C18—H19A0.9700
O3—C211.483 (4)C18—H19B0.9700
O4—C171.194 (4)C19—H66A0.9600
O5—C201.190 (4)C19—H66B0.9600
O6—C171.321 (4)C19—H66C0.9600
O6—C181.449 (4)C21—C221.458 (5)
N1—C141.422 (3)C21—H21A0.9700
N1—C71.438 (3)C21—H21B0.9700
C1—C61.363 (4)C22—H33A0.9600
C1—C21.372 (4)C22—H33B0.9600
C2—C31.370 (5)C22—H33C0.9600
C2—H20.9300C23—C241.522 (3)
C3—C41.354 (6)C23—H23A0.9700
C3—H30.9300C23—H23B0.9700
C4—C51.371 (6)C24—C291.392 (3)
C4—H40.9300C24—C251.396 (3)
C5—C61.386 (5)C25—C261.391 (3)
C5—H50.9300C25—C301.506 (4)
C6—H60.9300C26—C271.373 (4)
C7—C81.353 (3)C26—H260.9300
C7—C151.460 (3)C27—C281.375 (4)
C8—C91.441 (3)C27—C311.514 (4)
C8—C231.508 (3)C28—C291.387 (4)
C9—C141.391 (3)C28—H280.9300
C9—C101.396 (3)C29—C321.509 (4)
C10—C111.368 (4)C30—H30A0.9600
C10—H100.9300C30—H30B0.9600
C11—C121.389 (4)C30—H30C0.9600
C11—H110.9300C31—H31A0.9600
C12—C131.364 (4)C31—H31B0.9600
C12—H120.9300C31—H31C0.9600
C13—C141.388 (3)C32—H32A0.9600
C13—H130.9300C32—H32B0.9600
C15—C161.332 (4)C32—H32C0.9600
O2—S1—O1120.54 (13)C19—C18—H19B109.4
O2—S1—N1106.83 (11)H19A—C18—H19B108.0
O1—S1—N1105.76 (13)C18—C19—H66A109.5
O2—S1—C1109.32 (13)C18—C19—H66B109.5
O1—S1—C1108.79 (13)H66A—C19—H66B109.5
N1—S1—C1104.36 (11)C18—C19—H66C109.5
C20—O3—C21116.6 (3)H66A—C19—H66C109.5
C17—O6—C18117.1 (3)H66B—C19—H66C109.5
C14—N1—C7106.24 (18)O5—C20—O3124.2 (3)
C14—N1—S1115.80 (16)O5—C20—C16123.4 (3)
C7—N1—S1120.08 (16)O3—C20—C16112.5 (3)
C6—C1—C2120.7 (3)C22—C21—O3105.9 (4)
C6—C1—S1118.6 (2)C22—C21—H21A110.5
C2—C1—S1120.7 (2)O3—C21—H21A110.5
C3—C2—C1119.4 (3)C22—C21—H21B110.5
C3—C2—H2120.3O3—C21—H21B110.5
C1—C2—H2120.3H21A—C21—H21B108.7
C4—C3—C2120.6 (4)C21—C22—H33A109.5
C4—C3—H3119.7C21—C22—H33B109.5
C2—C3—H3119.7H33A—C22—H33B109.5
C3—C4—C5120.2 (4)C21—C22—H33C109.5
C3—C4—H4119.9H33A—C22—H33C109.5
C5—C4—H4119.9H33B—C22—H33C109.5
C4—C5—C6119.7 (4)C8—C23—C24116.5 (2)
C4—C5—H5120.1C8—C23—H23A108.2
C6—C5—H5120.1C24—C23—H23A108.2
C1—C6—C5119.3 (3)C8—C23—H23B108.2
C1—C6—H6120.4C24—C23—H23B108.2
C5—C6—H6120.4H23A—C23—H23B107.3
C8—C7—N1109.75 (19)C29—C24—C25119.5 (2)
C8—C7—C15128.0 (2)C29—C24—C23119.0 (2)
N1—C7—C15121.3 (2)C25—C24—C23121.5 (2)
C7—C8—C9107.7 (2)C26—C25—C24118.9 (2)
C7—C8—C23128.9 (2)C26—C25—C30119.0 (2)
C9—C8—C23123.0 (2)C24—C25—C30122.1 (2)
C14—C9—C10119.5 (2)C27—C26—C25122.4 (3)
C14—C9—C8108.2 (2)C27—C26—H26118.8
C10—C9—C8132.3 (2)C25—C26—H26118.8
C11—C10—C9118.7 (3)C26—C27—C28117.6 (2)
C11—C10—H10120.6C26—C27—C31122.1 (3)
C9—C10—H10120.6C28—C27—C31120.2 (3)
C10—C11—C12120.8 (3)C27—C28—C29122.3 (2)
C10—C11—H11119.6C27—C28—H28118.9
C12—C11—H11119.6C29—C28—H28118.9
C13—C12—C11121.7 (3)C28—C29—C24119.3 (2)
C13—C12—H12119.1C28—C29—C32119.1 (3)
C11—C12—H12119.1C24—C29—C32121.6 (3)
C12—C13—C14117.7 (3)C25—C30—H30A109.5
C12—C13—H13121.1C25—C30—H30B109.5
C14—C13—H13121.1H30A—C30—H30B109.5
C13—C14—C9121.5 (2)C25—C30—H30C109.5
C13—C14—N1130.4 (2)H30A—C30—H30C109.5
C9—C14—N1108.11 (19)H30B—C30—H30C109.5
C16—C15—C7126.1 (2)C27—C31—H31A109.5
C16—C15—H15120.2 (19)C27—C31—H31B109.5
C7—C15—H15113.4 (19)H31A—C31—H31B109.5
C15—C16—C17124.2 (2)C27—C31—H31C109.5
C15—C16—C20122.8 (3)H31A—C31—H31C109.5
C17—C16—C20113.0 (2)H31B—C31—H31C109.5
O4—C17—O6124.2 (3)C29—C32—H32A109.5
O4—C17—C16123.9 (3)C29—C32—H32B109.5
O6—C17—C16112.0 (2)H32A—C32—H32B109.5
O6—C18—C19111.3 (4)C29—C32—H32C109.5
O6—C18—H19A109.4H32A—C32—H32C109.5
C19—C18—H19A109.4H32B—C32—H32C109.5
O6—C18—H19B109.4
O2—S1—N1—C14−167.56 (16)C7—N1—C14—C13−179.8 (3)
O1—S1—N1—C1462.87 (18)S1—N1—C14—C13−43.7 (3)
C1—S1—N1—C14−51.82 (18)C7—N1—C14—C90.0 (2)
O2—S1—N1—C7−37.8 (2)S1—N1—C14—C9136.08 (18)
O1—S1—N1—C7−167.42 (17)C8—C7—C15—C16−124.3 (3)
C1—S1—N1—C777.89 (19)N1—C7—C15—C1642.8 (4)
O2—S1—C1—C640.3 (3)C7—C15—C16—C17−0.3 (4)
O1—S1—C1—C6173.8 (2)C7—C15—C16—C20177.9 (2)
N1—S1—C1—C6−73.7 (3)C18—O6—C17—O4−2.7 (5)
O2—S1—C1—C2−141.1 (2)C18—O6—C17—C16176.6 (3)
O1—S1—C1—C2−7.6 (3)C15—C16—C17—O4−122.4 (3)
N1—S1—C1—C2104.9 (3)C20—C16—C17—O459.2 (4)
C6—C1—C2—C3−2.1 (5)C15—C16—C17—O658.3 (4)
S1—C1—C2—C3179.4 (3)C20—C16—C17—O6−120.1 (3)
C1—C2—C3—C41.6 (6)C17—O6—C18—C1994.3 (5)
C2—C3—C4—C50.4 (7)C21—O3—C20—O51.9 (6)
C3—C4—C5—C6−1.9 (7)C21—O3—C20—C16−178.8 (3)
C2—C1—C6—C50.6 (5)C15—C16—C20—O5−167.4 (3)
S1—C1—C6—C5179.2 (3)C17—C16—C20—O511.1 (4)
C4—C5—C6—C11.4 (7)C15—C16—C20—O313.4 (4)
C14—N1—C7—C80.4 (3)C17—C16—C20—O3−168.2 (3)
S1—N1—C7—C8−133.46 (18)C20—O3—C21—C2297.3 (6)
C14—N1—C7—C15−168.9 (2)C7—C8—C23—C24−46.2 (4)
S1—N1—C7—C1557.3 (3)C9—C8—C23—C24141.6 (2)
N1—C7—C8—C9−0.6 (3)C8—C23—C24—C29−74.8 (3)
C15—C7—C8—C9167.8 (2)C8—C23—C24—C25108.4 (3)
N1—C7—C8—C23−173.7 (2)C29—C24—C25—C260.4 (4)
C15—C7—C8—C23−5.4 (4)C23—C24—C25—C26177.2 (2)
C7—C8—C9—C140.5 (3)C29—C24—C25—C30−177.9 (2)
C23—C8—C9—C14174.2 (2)C23—C24—C25—C30−1.1 (4)
C7—C8—C9—C10−178.5 (2)C24—C25—C26—C27−0.5 (4)
C23—C8—C9—C10−4.9 (4)C30—C25—C26—C27177.9 (3)
C14—C9—C10—C111.0 (4)C25—C26—C27—C280.1 (4)
C8—C9—C10—C11−180.0 (2)C25—C26—C27—C31−178.8 (3)
C9—C10—C11—C120.2 (4)C26—C27—C28—C290.3 (4)
C10—C11—C12—C13−1.1 (5)C31—C27—C28—C29179.3 (3)
C11—C12—C13—C140.8 (4)C27—C28—C29—C24−0.3 (4)
C12—C13—C14—C90.4 (4)C27—C28—C29—C32−178.2 (3)
C12—C13—C14—N1−179.9 (2)C25—C24—C29—C280.0 (4)
C10—C9—C14—C13−1.3 (4)C23—C24—C29—C28−176.9 (2)
C8—C9—C14—C13179.5 (2)C25—C24—C29—C32177.8 (3)
C10—C9—C14—N1178.9 (2)C23—C24—C29—C320.9 (4)
C8—C9—C14—N1−0.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C10—H10···O4i0.932.433.179 (4)138
C13—H13···O10.932.483.030 (4)118

Symmetry codes: (i) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2550).

References

  • Bruker (2004). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3698.
  • Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542. [PMC free article] [PubMed]
  • Ma, C., Liu, X., Li, X., Flippen-Anderson, J., Yu, S. & Cook, J. M. (2001). J. Org. Chem.66, 4525–4542. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Zhao, S., Liao, X. & Cook, J. M. (2002). Org. Lett.4, 687–690. [PubMed]
  • Zhou, H., Liao, X., Yin, W., Ma, J. & Cook, J. M. (2006). J. Org. Chem.71, 251–259. [PubMed]

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