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 May 1; 66(Pt 5): o1159.
Published online 2010 April 24. doi:  10.1107/S1600536810014467
PMCID: PMC2979287

4-Methyl-N-[(2-oxo-1,3-thia­zolidin-3-yl)carbon­yl]benzene­sulfonamide

Abstract

The asymmetric unit of the title compound, C11H12N2O4S2, contains two independent mol­ecules with similar dihedral angles of 76.7 (1) and 77.3 (1)° between the mean planes of the five- and six-membered rings. In both mol­ecules, the amino groups are involved in intra­molecular N—H(...)O hydrogen bonds. In the crystal structure, weak inter­molecular C—H(...)O hydrogen bonds link mol­ecules into ribbons extended along the a axis.

Related literature

For a related structure, see: Gowda et al. (2010 [triangle]). For details of the synthesis, see: Chen & Shen (2008 [triangle]). For the biological activity of related compounds, see: Fujimoto & Shimizu (1978 [triangle]); Liu et al. (2007 [triangle], 2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1159-scheme1.jpg

Experimental

Crystal data

  • C11H12N2O4S2
  • M r = 300.35
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1159-efi1.jpg
  • a = 9.5560 (4) Å
  • b = 9.6722 (4) Å
  • c = 14.6352 (6) Å
  • α = 88.7232 (10)°
  • β = 86.3267 (11)°
  • γ = 76.5399 (11)°
  • V = 1312.80 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.42 mm−1
  • T = 296 K
  • 0.39 × 0.36 × 0.14 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.825, T max = 0.943
  • 13020 measured reflections
  • 5941 independent reflections
  • 4475 reflections with F 2 > 2σ(F 2)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.153
  • S = 1.00
  • 5941 reflections
  • 345 parameters
  • H-atom parameters constrained
  • Δρmax = 0.52 e Å−3
  • Δρmin = −0.38 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 2006 [triangle]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014467/cv2707sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014467/cv2707Isup2.hkl

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

Acknowledgments

This work was funded by the National Natural Science Foundation (grant No. 30900959), the Natural Science Foundation of Zhejiang Province (grant No. Y3080096) and the Zhejiang University of Technology Research Fund (grant No. X 1017104).

supplementary crystallographic information

Comment

2-Thiazolidione derivatives are known as fungicides, insecticides and plant growth regulators (Chen et al. 2008; Fujimoto et al. 1978). Meanwhile, many pesticides contain amide fragments (Liu et al. 2007; Liu et al. 2009) . Herewith we present the title compound (I) - a new thiazolidione derivative synthesized by the reaction of 2-thiazolidione and 4-methyl-benzenesulfonylisocyanate.

In (I) (Fig. 1), the carboxamide moiety is nearly coplanar with the thiazole ring [dihedral angle 7.2 (2)°]. The C4-O12 bond length of 1.202 (3) Å is normal for C=O double bond. The conformation of C—SO2—NH—C(O) fragment is similar to that observed in N-Benzoyl-2-chlorobenzenesulfonamide (Gowda et al., 2010). Amino groups in two independent molecules are involved in intramolecular N—H···O hydrogen bonds (Table 1). In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules into ribbons extended along the axis a.

Experimental

The title compound was synthesized according to Chen et al. (2008). 2-Thiazolidiones (1.03 g, 0.01 mol) and 4-methyl- benzenesulfonylisocyanate (1.97 g,0.01 mol) were dissolved in anhydrous acetone(15 ml)with stirring. The mixture was then stirred at room temperature for 15 h. The solution was evaporated in a rotary evaporator at 30 degree under reduced pressure till 1.5 g of solide residue were obtained. This was washed three times with water and dried. Colourless single crystals suitable for crystallographic analysis were obtained by slow evaporation of an acetone-petroleum ether (1:20 v/v) solution.

Refinement

All H atoms were geometrically positioned (C—H 0.93-0.97 Å; N—H 0.86 Å), and refined as riding, with Uiso(H) = 1.2 Ueq(C, N).

Figures

Fig. 1.
The molecular structure of (I), showing displacement ellipsoids drawn at the 50% probability level.

Crystal data

C11H12N2O4S2Z = 4
Mr = 300.35F(000) = 624.00
Triclinic, P1Dx = 1.519 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 9.5560 (4) ÅCell parameters from 10300 reflections
b = 9.6722 (4) Åθ = 3.1–27.4°
c = 14.6352 (6) ŵ = 0.42 mm1
α = 88.7232 (10)°T = 296 K
β = 86.3267 (11)°Platelet, colourless
γ = 76.5399 (11)°0.39 × 0.36 × 0.14 mm
V = 1312.80 (9) Å3

Data collection

Rigaku R-AXIS RAPID diffractometer4475 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.019
ω scansθmax = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −12→12
Tmin = 0.825, Tmax = 0.943k = −10→12
13020 measured reflectionsl = −18→18
5941 independent reflections

Refinement

Refinement on F2w = 1/[σ2(Fo2) + (0.0833P)2 + 0.8006P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.048(Δ/σ)max = 0.001
wR(F2) = 0.153Δρmax = 0.52 e Å3
S = 1.00Δρmin = −0.38 e Å3
5941 reflectionsExtinction correction: SHELXL97 (Sheldrick, 2008)
345 parametersExtinction coefficient: 0.0029 (10)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

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

xyzUiso*/Ueq
S110.70694 (8)0.42660 (8)0.60372 (5)0.0526 (2)
S120.33746 (6)0.09549 (6)0.40275 (4)0.03965 (16)
S311.11065 (8)−0.10590 (9)0.27249 (5)0.0583 (2)
S320.72340 (8)0.38204 (6)0.06460 (5)0.04988 (18)
O110.6604 (2)0.3008 (2)0.45563 (12)0.0524 (4)
O120.2711 (2)0.2641 (2)0.57769 (12)0.0538 (4)
O130.2613 (2)0.0224 (2)0.46669 (12)0.0489 (4)
O140.4392 (2)0.0178 (2)0.33572 (12)0.0505 (4)
O311.0687 (2)0.0667 (2)0.13083 (14)0.0704 (6)
O320.6590 (2)0.2350 (2)0.24079 (13)0.0598 (5)
O330.6406 (2)0.4885 (2)0.12455 (14)0.0596 (5)
O340.8234 (2)0.4156 (2)−0.00386 (16)0.0681 (6)
N110.4892 (2)0.3182 (2)0.57686 (12)0.0380 (4)
N120.4356 (2)0.1810 (2)0.45973 (13)0.0416 (4)
N310.8833 (2)0.0924 (2)0.24434 (13)0.0440 (4)
N320.8270 (2)0.2587 (2)0.12745 (16)0.0531 (5)
C10.6163 (2)0.3371 (2)0.53329 (17)0.0390 (5)
C20.5766 (3)0.4345 (4)0.6988 (2)0.0638 (8)
C30.4517 (3)0.3829 (3)0.66798 (18)0.0528 (6)
C40.3885 (2)0.2544 (2)0.54018 (17)0.0393 (5)
C50.2141 (2)0.2307 (2)0.34841 (16)0.0382 (5)
C60.0829 (2)0.2946 (3)0.39243 (18)0.0484 (6)
C7−0.0075 (2)0.4065 (3)0.3507 (2)0.0514 (6)
C80.0293 (2)0.4558 (2)0.26469 (18)0.0430 (5)
C90.1602 (2)0.3878 (2)0.22135 (18)0.0492 (6)
C100.2527 (2)0.2758 (2)0.26209 (17)0.0462 (5)
C11−0.0668 (3)0.5805 (3)0.2195 (2)0.0579 (7)
C311.0186 (2)0.0317 (2)0.20360 (18)0.0457 (5)
C320.9758 (3)−0.0719 (3)0.36468 (19)0.0549 (6)
C330.8416 (3)0.0248 (3)0.32863 (18)0.0552 (7)
C340.7786 (2)0.2013 (2)0.20679 (17)0.0431 (5)
C350.6085 (2)0.2939 (2)0.01393 (17)0.0454 (5)
C360.4716 (3)0.3001 (3)0.05305 (19)0.0519 (6)
C370.3815 (3)0.2319 (3)0.0121 (2)0.0613 (7)
C380.4260 (3)0.1557 (2)−0.0680 (2)0.0594 (7)
C390.5622 (4)0.1492 (3)−0.1052 (2)0.0691 (9)
C400.6540 (3)0.2172 (3)−0.0651 (2)0.0640 (8)
C410.3275 (4)0.0852 (3)−0.1184 (3)0.0843 (11)
H60.05620.26220.44970.058*
H7−0.09500.44990.38060.062*
H90.18610.41870.16340.059*
H100.33970.23130.23200.055*
H120.52150.17960.43780.050*
H320.91610.22900.10920.064*
H360.44070.35040.10690.062*
H370.28930.23680.03850.074*
H390.59350.0978−0.15860.083*
H400.74640.2113−0.09130.077*
H111−0.09470.65780.26190.069*
H112−0.15130.55360.20110.069*
H113−0.01580.60980.16670.069*
H2010.61990.37450.74830.077*
H2020.54400.53170.71980.077*
H3010.42910.31260.71120.063*
H3020.36870.46220.66470.063*
H3210.9545−0.16050.38670.066*
H3221.0094−0.02570.41430.066*
H3310.7725−0.03070.31610.066*
H3320.79860.09680.37370.066*
H4110.3605−0.0162−0.11400.101*
H4120.32880.1137−0.18160.101*
H4130.23100.1135−0.09150.101*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S110.0476 (3)0.0585 (4)0.0574 (4)−0.0234 (3)−0.0027 (2)−0.0058 (3)
S120.0403 (3)0.0369 (2)0.0419 (3)−0.0088 (2)−0.0039 (2)−0.0024 (2)
S310.0489 (4)0.0606 (4)0.0561 (4)0.0039 (3)0.0030 (3)0.0065 (3)
S320.0506 (3)0.0487 (3)0.0487 (3)−0.0095 (2)−0.0010 (2)0.0084 (2)
O110.0514 (11)0.0589 (11)0.0493 (10)−0.0207 (9)0.0110 (8)−0.0083 (8)
O120.0405 (10)0.0667 (12)0.0561 (11)−0.0180 (9)0.0075 (8)−0.0143 (9)
O130.0557 (11)0.0470 (9)0.0482 (9)−0.0205 (8)−0.0062 (8)0.0069 (8)
O140.0501 (10)0.0454 (9)0.0516 (10)−0.0023 (8)0.0004 (8)−0.0113 (8)
O310.0567 (12)0.0821 (15)0.0581 (12)0.0059 (11)0.0174 (10)0.0146 (11)
O320.0471 (11)0.0673 (13)0.0561 (11)0.0019 (9)0.0060 (9)0.0031 (9)
O330.0660 (13)0.0463 (10)0.0644 (12)−0.0075 (9)−0.0076 (10)−0.0037 (9)
O340.0636 (13)0.0741 (14)0.0673 (13)−0.0216 (11)0.0032 (10)0.0216 (11)
N110.0359 (10)0.0406 (10)0.0373 (10)−0.0087 (8)0.0007 (7)−0.0039 (8)
N120.0341 (10)0.0474 (11)0.0433 (10)−0.0096 (8)0.0000 (8)−0.0083 (9)
N310.0410 (11)0.0481 (11)0.0408 (10)−0.0073 (9)0.0009 (8)0.0011 (9)
N320.0419 (12)0.0627 (14)0.0506 (12)−0.0056 (10)0.0013 (9)0.0092 (11)
C10.0360 (11)0.0334 (11)0.0471 (13)−0.0078 (9)−0.0001 (9)0.0014 (10)
C20.0552 (17)0.084 (2)0.0548 (16)−0.0200 (16)−0.0016 (13)−0.0195 (15)
C30.0529 (16)0.0683 (17)0.0407 (13)−0.0223 (13)0.0061 (11)−0.0132 (12)
C40.0350 (11)0.0391 (11)0.0430 (12)−0.0073 (9)−0.0013 (9)−0.0002 (10)
C50.0366 (11)0.0393 (11)0.0398 (11)−0.0103 (9)−0.0036 (9)−0.0008 (9)
C60.0381 (13)0.0599 (16)0.0454 (13)−0.0104 (11)0.0060 (10)0.0061 (12)
C70.0326 (12)0.0616 (16)0.0557 (15)−0.0044 (11)0.0051 (11)0.0016 (13)
C80.0392 (12)0.0450 (13)0.0462 (13)−0.0111 (10)−0.0072 (10)−0.0010 (10)
C90.0491 (14)0.0543 (15)0.0412 (13)−0.0074 (12)0.0018 (11)0.0050 (11)
C100.0421 (13)0.0502 (14)0.0419 (12)−0.0041 (11)0.0065 (10)−0.0002 (11)
C110.0495 (16)0.0558 (16)0.0660 (18)−0.0064 (13)−0.0095 (13)0.0051 (14)
C310.0377 (12)0.0492 (14)0.0464 (13)−0.0036 (10)0.0021 (10)−0.0010 (11)
C320.0491 (15)0.0696 (18)0.0451 (14)−0.0122 (13)−0.0052 (11)0.0085 (13)
C330.0472 (15)0.0683 (18)0.0440 (14)−0.0040 (13)0.0049 (11)0.0050 (13)
C340.0393 (13)0.0457 (13)0.0424 (12)−0.0057 (10)−0.0036 (10)−0.0025 (10)
C350.0516 (14)0.0437 (13)0.0363 (12)−0.0022 (11)−0.0018 (10)0.0036 (10)
C360.0560 (16)0.0554 (15)0.0430 (13)−0.0113 (13)0.0034 (11)−0.0048 (11)
C370.0659 (19)0.0620 (18)0.0563 (17)−0.0150 (15)−0.0058 (14)−0.0024 (14)
C380.076 (2)0.0405 (14)0.0592 (17)−0.0052 (14)−0.0201 (15)0.0057 (12)
C390.088 (2)0.0600 (18)0.0517 (16)−0.0011 (17)−0.0036 (16)−0.0183 (14)
C400.0616 (19)0.0688 (19)0.0528 (16)0.0001 (15)0.0099 (14)−0.0099 (14)
C410.086 (2)0.0507 (17)0.121 (3)−0.0136 (17)−0.050 (2)−0.0125 (19)

Geometric parameters (Å, °)

S11—C11.750 (2)C32—C331.518 (3)
S11—C21.797 (3)C35—C361.383 (4)
S12—O131.424 (2)C35—C401.379 (3)
S12—O141.4295 (18)C36—C371.373 (5)
S12—N121.658 (2)C37—C381.389 (4)
S12—C51.757 (2)C38—C391.366 (5)
S31—C311.752 (2)C38—C411.517 (5)
S31—C321.786 (2)C39—C401.378 (5)
S32—O331.424 (2)N12—H120.860
S32—O341.425 (2)N32—H320.860
S32—N321.663 (2)C2—H2010.970
S32—C351.747 (3)C2—H2020.970
O11—C11.217 (3)C3—H3010.970
O12—C41.202 (3)C3—H3020.970
O31—C311.213 (3)C6—H60.930
O32—C341.192 (3)C7—H70.930
N11—C11.384 (3)C9—H90.930
N11—C31.473 (3)C10—H100.930
N11—C41.397 (3)C11—H1110.960
N12—C41.383 (3)C11—H1120.960
N31—C311.391 (3)C11—H1130.960
N31—C331.460 (3)C32—H3210.970
N31—C341.402 (3)C32—H3220.970
N32—C341.376 (3)C33—H3310.970
C2—C31.494 (4)C33—H3320.970
C5—C61.387 (3)C36—H360.930
C5—C101.383 (3)C37—H370.930
C6—C71.376 (3)C39—H390.930
C7—C81.389 (3)C40—H400.930
C8—C91.390 (3)C41—H4110.960
C8—C111.504 (3)C41—H4120.960
C9—C101.380 (3)C41—H4130.960
C1—S11—C293.82 (15)C39—C38—C41118.6 (2)
O13—S12—O14120.18 (11)C38—C39—C40121.3 (2)
O13—S12—N12108.77 (11)C35—C40—C39119.9 (3)
O13—S12—C5109.42 (11)S12—N12—H12117.8
O14—S12—N12103.25 (11)C4—N12—H12117.8
O14—S12—C5109.48 (10)S32—N32—H32118.0
N12—S12—C5104.49 (11)C34—N32—H32118.0
C31—S31—C3293.95 (12)S11—C2—H201109.7
O33—S32—O34120.96 (14)S11—C2—H202109.7
O33—S32—N32108.22 (12)C3—C2—H201109.7
O33—S32—C35109.34 (13)C3—C2—H202109.7
O34—S32—N32102.86 (12)H201—C2—H202109.5
O34—S32—C35109.16 (13)N11—C3—H301109.5
N32—S32—C35105.02 (13)N11—C3—H302109.5
C1—N11—C3116.0 (2)C2—C3—H301109.5
C1—N11—C4126.5 (2)C2—C3—H302109.5
C3—N11—C4117.2 (2)H301—C3—H302109.5
S12—N12—C4124.46 (18)C5—C6—H6120.3
C31—N31—C33116.3 (2)C7—C6—H6120.3
C31—N31—C34125.9 (2)C6—C7—H7119.3
C33—N31—C34117.4 (2)C8—C7—H7119.3
S32—N32—C34123.93 (18)C8—C9—H9119.2
S11—C1—O11123.1 (2)C10—C9—H9119.2
S11—C1—N11111.07 (17)C5—C10—H10120.5
O11—C1—N11125.8 (2)C9—C10—H10120.5
S11—C2—C3108.6 (2)C8—C11—H111109.5
N11—C3—C2109.4 (2)C8—C11—H112109.5
O12—C4—N11121.0 (2)C8—C11—H113109.5
O12—C4—N12124.1 (2)H111—C11—H112109.5
N11—C4—N12114.9 (2)H111—C11—H113109.5
S12—C5—C6120.75 (18)H112—C11—H113109.5
S12—C5—C10118.64 (17)S31—C32—H321109.9
C6—C5—C10120.6 (2)S31—C32—H322109.9
C5—C6—C7119.5 (2)C33—C32—H321109.9
C6—C7—C8121.3 (2)C33—C32—H322109.9
C7—C8—C9118.0 (2)H321—C32—H322109.5
C7—C8—C11121.7 (2)N31—C33—H331109.8
C9—C8—C11120.3 (2)N31—C33—H332109.8
C8—C9—C10121.7 (2)C32—C33—H331109.8
C5—C10—C9119.0 (2)C32—C33—H332109.8
S31—C31—O31123.45 (19)H331—C33—H332109.5
S31—C31—N31110.43 (18)C35—C36—H36120.1
O31—C31—N31126.1 (2)C37—C36—H36120.1
S31—C32—C33107.76 (18)C36—C37—H37119.5
N31—C33—C32108.3 (2)C38—C37—H37119.5
O32—C34—N31121.5 (2)C38—C39—H39119.4
O32—C34—N32125.0 (2)C40—C39—H39119.4
N31—C34—N32113.5 (2)C35—C40—H40120.1
S32—C35—C36120.2 (2)C39—C40—H40120.1
S32—C35—C40120.2 (2)C38—C41—H411109.5
C36—C35—C40119.6 (2)C38—C41—H412109.5
C35—C36—C37119.8 (2)C38—C41—H413109.5
C36—C37—C38120.9 (3)H411—C41—H412109.5
C37—C38—C39118.5 (3)H411—C41—H413109.5
C37—C38—C41122.8 (3)H412—C41—H413109.5
C1—S11—C2—C3−7.7 (2)S12—N12—C4—N11179.73 (15)
C2—S11—C1—O11−179.1 (2)C31—N31—C33—C3215.7 (3)
C2—S11—C1—N112.52 (19)C33—N31—C31—S31−4.9 (3)
O13—S12—N12—C4−41.4 (2)C33—N31—C31—O31175.1 (3)
O13—S12—C5—C628.0 (2)C31—N31—C34—O32170.4 (2)
O13—S12—C5—C10−154.4 (2)C31—N31—C34—N32−7.4 (4)
O14—S12—N12—C4−170.14 (19)C34—N31—C31—S31−177.4 (2)
O14—S12—C5—C6161.6 (2)C34—N31—C31—O312.6 (4)
O14—S12—C5—C10−20.7 (2)C33—N31—C34—O32−2.0 (4)
N12—S12—C5—C6−88.3 (2)C33—N31—C34—N32−179.9 (2)
N12—S12—C5—C1089.3 (2)C34—N31—C33—C32−171.2 (2)
C5—S12—N12—C475.4 (2)S32—N32—C34—O32−1.8 (4)
C31—S31—C32—C3314.4 (2)S32—N32—C34—N31175.9 (2)
C32—S31—C31—O31174.0 (2)S11—C2—C3—N1110.7 (3)
C32—S31—C31—N31−6.0 (2)S12—C5—C6—C7175.8 (2)
O33—S32—N32—C3445.7 (2)S12—C5—C10—C9−176.0 (2)
O33—S32—C35—C36−19.4 (2)C6—C5—C10—C91.6 (4)
O33—S32—C35—C40160.9 (2)C10—C5—C6—C7−1.8 (4)
O34—S32—N32—C34174.9 (2)C5—C6—C7—C80.7 (4)
O34—S32—C35—C36−153.8 (2)C6—C7—C8—C90.6 (4)
O34—S32—C35—C4026.5 (2)C6—C7—C8—C11−178.3 (2)
N32—S32—C35—C3696.5 (2)C7—C8—C9—C10−0.8 (4)
N32—S32—C35—C40−83.2 (2)C11—C8—C9—C10178.1 (2)
C35—S32—N32—C34−71.0 (2)C8—C9—C10—C5−0.3 (4)
C1—N11—C3—C2−9.6 (3)S31—C32—C33—N31−18.7 (3)
C3—N11—C1—S113.8 (2)S32—C35—C36—C37179.2 (2)
C3—N11—C1—O11−174.5 (2)S32—C35—C40—C39−179.3 (2)
C1—N11—C4—O12−167.6 (2)C36—C35—C40—C391.0 (4)
C1—N11—C4—N1212.8 (3)C40—C35—C36—C37−1.0 (4)
C4—N11—C1—S11178.29 (17)C35—C36—C37—C380.4 (4)
C4—N11—C1—O110.0 (3)C36—C37—C38—C390.4 (4)
C3—N11—C4—O126.9 (3)C36—C37—C38—C41−176.7 (2)
C3—N11—C4—N12−172.8 (2)C37—C38—C39—C40−0.5 (4)
C4—N11—C3—C2175.3 (2)C41—C38—C39—C40176.7 (2)
S12—N12—C4—O120.1 (2)C38—C39—C40—C35−0.2 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N12—H12···O110.862.002.665 (3)134
N32—H32···O310.861.912.608 (3)137
C33—H332···O110.972.403.352 (3)166
C11—H112···O33i0.962.553.500 (4)170
C32—H321···O12ii0.972.603.384 (3)138

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2707).

References

  • Chen, Q. W. & Shen, D. L. (2008). J. Zhejiang Univ. Technol.36, 562–564.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Fujimoto, E. & Shimizu, T. (1978). Jpn Patent JP 53127466.
  • Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o794. [PMC free article] [PubMed]
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Liu, X. H., Chen, P. Q., Wang, B. L., Li, Y. H., Wang, S. H. & Li, Z. M. (2007). Bioorg. Med. Chem. Lett.17, 3784–3788. [PubMed]
  • Liu, X. H., Shi, Y. X., Ma, Y., He, G. R., Dong, W. L., Zhang, C. Y., Wang, B. L., Wang, S. H., Li, B. J. & Li, Z. M. (2009). Chem. Biol. Drug Des.73, 320–327. [PubMed]
  • Rigaku (2006). PROCESS-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku (2007). CrystalStructure Rigaku Americas Corporation, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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