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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2289.
Published online 2008 November 8. doi:  10.1107/S1600536808036003
PMCID: PMC2960108

2,2′,4,4′,6,6′-Hexamethyl-N-(3-phthalimidoprop­yl)-N,N′-(propane-1,3-di­yl)dibenzene­sulfonamide

Abstract

In the title compound, C32H38N3O6S2, an inter­mediate in the synthesis of polyamine drugs, the dihedral angle between the phenyl rings of the two 2,4,6-trimethyl­benzene­sulfonyl groups is 27.1 (3)°. In the crystal structure, mol­ecules are linked by inter­molecular N—H(...)O hydrogen bonds, thereby forming an infinite one-dimensional chain propagating along [010].

Related literature

Polyamines are essential growth factors for cells, existing mainly as polycations at physiological pH, see: Cullis et al. (1999 [triangle]); Seiler et al. (1996 [triangle]); Tsen et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2289-scheme1.jpg

Experimental

Crystal data

  • C32H39N3O6S2
  • M r = 625.78
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2289-efi1.jpg
  • a = 32.042 (3) Å
  • b = 9.9782 (8) Å
  • c = 25.105 (2) Å
  • β = 127.917 (1)°
  • V = 6332.1 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.22 mm−1
  • T = 296 (2) K
  • 0.18 × 0.15 × 0.13 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001 [triangle]) T min = 0.962, T max = 0.973
  • 17128 measured reflections
  • 6212 independent reflections
  • 4574 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.069
  • wR(F 2) = 0.219
  • S = 1.09
  • 6212 reflections
  • 388 parameters
  • 44 restraints
  • H-atom parameters constrained
  • Δρmax = 0.80 e Å−3
  • Δρmin = −0.57 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036003/hb2835sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036003/hb2835Isup2.hkl

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

Acknowledgments

This work was supported by the Basic Research Foundation for Natural Science of Henan University.

supplementary crystallographic information

Comment

Polyamines are essential growth factors for cells, which exist mainly as polycations at physiological pH (Cullis et al., 1999; Seiler et al., 1996; Tsen et al., 2008). As part of our studies in this area, herein we report the synthesis and structure of the title compound, (I).

The compound (I) consists of a polyamine chain with two 2,4,6-trimethylbenzenesulfonyl group acting as protecting groups (Fig. 1). In the structure of (I), the two phenyl ring of two 2,4,6-trimethylbenzenesulfonyl group are nonparallel due to steric hindrance, charactrtized by a dihedral angel of 27.1 (3) °.

In the crystal, molecules are linked through intermolecular N–H···O hydrogen bonds to construct an infinite one-dimensional chain (Fig. 2 and Table 1).

Experimental

Propane-1,3-diamine 1.85 g (25 mmol) was dissolved in 2 M sodium hydroxide and the solution was cooled to 0 °C, a solution of 2,4,6-trimethylbenzenesulfonyl chloride 10.9 g (50 mmol) in CH2Cl2 (25 ml) was added dropwise. The reaction mixture was then stirred at room temperture for 18 h. The organic phase was separated from the aqueous phase and washed with 0.5 M HCl solution and brine. The CH2Cl2 layer was dried over sodium sulfate, filtered and the solvent removed in vacuo, and the residue purified by chromatography.

A mixture of N1,N3—Bis(mesitylenesulfonyl)-1,3-propyl-diamine 1.05 g (2.33 mmol) and 60% NaH (5.35 mmol, 0.22 g) in DMF 20 ml was stirred at 0 °C for 0.5 h, then warmed to room temperature for 0.5 h. N-(3-bromopropyl)phthalimide 1.57 g (5.82 mmol) was added and the reaction mixture was stirred at 40 °C for 4 h, then EtoH (2.5 ml) and water (5 ml) were added, the solvent was removed in vacuo at 80 °C, the residue was dissolved in CHCl3 and washed with water, the organic layer was dried over anhydrous sodium sulfate and filtered, then concentrated in vacuo, the residue was purified by chromatography. Colorless rod crystal of (I) were obtained.

Refinement

The H atoms were positioned geogmetrically (N—H = 0.86 Å, C—H = 0.93–0.97Å) and refined as riding with Uiso(H)=1.2Ueq(carrier) or Uiso(H)=1.5Ueq(methyl-C).

Figures

Fig. 1.
The molecular structure of (I). Displacement ellipsoids for the non-hydrogen atoms are drawn at the 50% probability level.
Fig. 2.
One-dimensional structure of (I), Hydrogen bonds are shown as dashed lines. For clarity, H atoms not involved in hydrogen bonds are omitted.

Crystal data

C32H39N3O6S2F000 = 2656
Mr = 625.78Dx = 1.313 Mg m3
Monoclinic, C2/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 6528 reflections
a = 32.042 (3) Åθ = 2.4–28.1º
b = 9.9782 (8) ŵ = 0.22 mm1
c = 25.105 (2) ÅT = 296 (2) K
β = 127.917 (1)ºBlock, colourless
V = 6332.1 (9) Å30.18 × 0.15 × 0.13 mm
Z = 8

Data collection

Bruker SMART CCD diffractometer6212 independent reflections
Radiation source: fine-focus sealed tube4574 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.022
T = 296(2) Kθmax = 26.0º
ω scansθmin = 2.1º
Absorption correction: Multi-scan(SADABS; Sheldrick, 2001)h = −25→39
Tmin = 0.962, Tmax = 0.973k = −12→11
17128 measured reflectionsl = −30→21

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.219  w = 1/[σ2(Fo2) + (0.1169P)2 + 7.2057P] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
6212 reflectionsΔρmax = 0.80 e Å3
388 parametersΔρmin = −0.57 e Å3
44 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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
S10.15326 (3)0.47012 (8)0.46771 (4)0.0531 (3)
S20.06920 (4)0.72487 (9)0.64731 (6)0.0655 (3)
C10.14805 (12)0.2922 (3)0.45787 (15)0.0464 (7)
C20.10216 (14)0.2310 (3)0.40203 (16)0.0539 (8)
C30.10074 (16)0.0918 (4)0.39911 (18)0.0635 (9)
H3A0.07030.05020.36260.076*
C40.1424 (2)0.0131 (4)0.4479 (2)0.0757 (9)
C50.18654 (16)0.0764 (4)0.50242 (19)0.0637 (9)
H5A0.21480.02420.53610.076*
C60.19082 (13)0.2140 (3)0.50937 (17)0.0546 (8)
C70.24128 (15)0.2685 (4)0.57208 (19)0.0734 (10)
H7A0.26440.19560.59920.110*
H7B0.23340.31940.59740.110*
H7C0.25830.32530.55970.110*
C80.1398 (2)−0.1383 (4)0.4422 (2)0.0849 (10)
H8A0.1062−0.16450.40140.127*
H8B0.1439−0.17630.48030.127*
H8C0.1676−0.17000.44130.127*
C90.05315 (15)0.3038 (5)0.34304 (18)0.0761 (11)
H9A0.02730.23930.31140.114*
H9B0.06270.35980.32100.114*
H9C0.03850.35800.35950.114*
C100.10008 (13)0.4624 (3)0.51695 (17)0.0581 (8)
H10A0.09980.36560.52030.070*
H10B0.06910.48880.47240.070*
C110.09849 (17)0.5273 (4)0.5705 (2)0.0732 (10)
H11A0.07400.47920.57400.088*
H11B0.13330.52360.61400.088*
C120.08133 (16)0.6696 (4)0.55154 (18)0.0698 (10)
H12A0.04320.67190.51710.084*
H12B0.09720.70700.53210.084*
C130.05511 (12)0.8878 (3)0.66060 (17)0.0512 (7)
C140.08566 (13)0.9494 (4)0.72467 (17)0.0554 (8)
C150.07141 (15)1.0790 (4)0.7284 (2)0.0718 (10)
H15A0.09101.12110.77020.086*
C160.03042 (19)1.1470 (5)0.6740 (3)0.1001 (12)
C170.00179 (16)1.0841 (4)0.6122 (2)0.0822 (12)
H17A−0.02591.13060.57450.099*
C180.01232 (15)0.9547 (5)0.6035 (2)0.0743 (9)
C19−0.02361 (16)0.8980 (5)0.5329 (2)0.0848 (10)
H19A−0.04940.96410.50280.127*
H19B−0.04130.82010.53260.127*
H19C−0.00300.87370.51850.127*
C200.0171 (2)1.2887 (5)0.6807 (3)0.1087 (13)
H20A0.04041.31530.72730.163*
H20B−0.01881.29220.66460.163*
H20C0.02151.34840.65450.163*
C210.13243 (15)0.8889 (5)0.78906 (18)0.0743 (11)
H21A0.14620.95170.82530.111*
H21B0.15930.86790.78440.111*
H21C0.12170.80850.79870.111*
C220.14972 (14)0.8142 (4)0.65501 (19)0.0644 (9)
H22A0.17540.74240.67170.077*
H22B0.15470.85520.69360.077*
C230.16017 (16)0.9152 (4)0.62171 (19)0.0692 (10)
H23A0.12950.97320.59460.083*
H23B0.16470.86990.59140.083*
C240.20845 (15)1.0008 (4)0.67022 (18)0.0644 (9)
H24A0.23890.94300.69910.077*
H24B0.21521.05700.64470.077*
C250.16924 (18)1.1983 (4)0.68724 (19)0.0795 (9)
C260.17520 (14)1.2568 (3)0.74571 (17)0.0596 (8)
C270.15189 (16)1.3666 (4)0.7500 (2)0.0748 (11)
H27A0.12801.41900.71230.090*
C280.16498 (18)1.3968 (4)0.8121 (2)0.0789 (11)
H28A0.14971.47120.81620.095*
C290.20005 (17)1.3201 (4)0.8680 (2)0.0719 (10)
H29A0.20801.34290.90930.086*
C300.22369 (14)1.2090 (4)0.86355 (18)0.0636 (9)
H30A0.24741.15650.90130.076*
C310.21105 (12)1.1789 (3)0.80191 (16)0.0528 (7)
C320.22889 (12)1.0682 (3)0.78088 (16)0.0522 (7)
O10.20542 (11)0.5116 (3)0.49361 (14)0.0727 (7)
O20.11048 (11)0.5309 (3)0.40790 (13)0.0741 (7)
O30.10576 (13)0.6647 (3)0.71039 (18)0.0900 (9)
O40.14220 (13)1.2330 (3)0.62932 (13)0.0890 (8)
O50.26026 (10)0.9802 (3)0.81456 (12)0.0691 (7)
O60.02164 (12)0.6529 (3)0.59969 (18)0.0939 (10)
N10.20210 (11)1.0851 (3)0.71198 (13)0.0566 (7)
N20.09614 (12)0.7566 (3)0.61035 (16)0.0662 (8)
N30.14813 (10)0.5046 (3)0.52664 (13)0.0523 (6)
H3B0.17290.54660.56260.063*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0687 (5)0.0447 (4)0.0570 (5)0.0021 (4)0.0443 (4)0.0024 (3)
S20.0762 (6)0.0477 (5)0.0974 (7)−0.0042 (4)0.0659 (6)−0.0118 (5)
C10.0573 (17)0.0451 (15)0.0488 (16)0.0052 (13)0.0387 (15)0.0006 (13)
C20.0663 (19)0.0585 (19)0.0489 (16)0.0028 (15)0.0414 (16)−0.0046 (14)
C30.082 (2)0.061 (2)0.0574 (19)−0.0106 (18)0.0483 (19)−0.0156 (16)
C40.127 (3)0.0491 (15)0.094 (2)0.0034 (17)0.089 (2)−0.0075 (15)
C50.085 (2)0.0552 (19)0.068 (2)0.0204 (18)0.056 (2)0.0112 (17)
C60.0643 (19)0.0556 (18)0.0589 (18)0.0071 (15)0.0454 (17)0.0024 (15)
C70.060 (2)0.078 (3)0.062 (2)0.0080 (19)0.0281 (18)0.0070 (19)
C80.131 (3)0.0509 (15)0.098 (2)0.0032 (17)0.083 (2)−0.0078 (15)
C90.064 (2)0.090 (3)0.054 (2)0.005 (2)0.0263 (18)−0.0025 (19)
C100.0620 (19)0.0545 (18)0.0641 (19)−0.0097 (15)0.0420 (17)−0.0172 (15)
C110.079 (2)0.067 (2)0.087 (3)−0.0039 (19)0.058 (2)−0.010 (2)
C120.069 (2)0.076 (2)0.065 (2)0.0016 (19)0.0412 (19)−0.0101 (16)
C130.0510 (16)0.0481 (16)0.0657 (19)0.0003 (13)0.0415 (16)−0.0056 (14)
C140.0531 (17)0.062 (2)0.0628 (19)0.0002 (15)0.0417 (16)−0.0057 (16)
C150.067 (2)0.069 (2)0.089 (3)−0.0076 (18)0.053 (2)−0.029 (2)
C160.083 (2)0.068 (2)0.151 (3)0.0135 (17)0.073 (2)−0.015 (2)
C170.061 (2)0.074 (2)0.098 (3)0.0204 (19)0.042 (2)0.009 (2)
C180.0549 (15)0.093 (2)0.0681 (17)0.0012 (15)0.0343 (14)−0.0060 (16)
C190.0613 (16)0.097 (2)0.0718 (17)0.0007 (15)0.0288 (14)−0.0062 (16)
C200.088 (2)0.070 (2)0.155 (3)0.0145 (17)0.069 (2)−0.015 (2)
C210.070 (2)0.099 (3)0.059 (2)0.007 (2)0.0428 (19)0.004 (2)
C220.065 (2)0.062 (2)0.077 (2)0.0052 (17)0.0488 (19)−0.0013 (18)
C230.079 (2)0.071 (2)0.069 (2)−0.0127 (19)0.051 (2)−0.0134 (18)
C240.068 (2)0.071 (2)0.067 (2)−0.0084 (18)0.0480 (19)−0.0093 (18)
C250.1013 (19)0.0670 (16)0.0558 (13)0.0131 (14)0.0410 (14)0.0110 (12)
C260.0613 (19)0.0478 (17)0.0597 (19)−0.0017 (15)0.0321 (17)0.0019 (14)
C270.077 (2)0.054 (2)0.082 (3)0.0068 (18)0.043 (2)0.0018 (18)
C280.094 (3)0.051 (2)0.108 (3)0.002 (2)0.070 (3)−0.009 (2)
C290.087 (3)0.063 (2)0.081 (3)−0.018 (2)0.059 (2)−0.020 (2)
C300.064 (2)0.065 (2)0.0557 (19)−0.0042 (17)0.0340 (17)−0.0022 (16)
C310.0471 (16)0.0491 (17)0.0546 (17)−0.0055 (13)0.0274 (14)−0.0026 (14)
C320.0422 (15)0.0573 (18)0.0510 (16)−0.0027 (14)0.0255 (14)0.0013 (14)
O10.0816 (17)0.0666 (16)0.0918 (18)−0.0112 (13)0.0644 (15)−0.0050 (14)
O20.0906 (18)0.0586 (15)0.0659 (15)0.0090 (13)0.0444 (14)0.0070 (12)
O30.115 (2)0.0606 (16)0.125 (3)0.0143 (16)0.090 (2)0.0101 (17)
O40.1081 (18)0.0715 (15)0.0585 (12)0.0151 (13)0.0364 (13)0.0111 (11)
O50.0614 (14)0.0711 (16)0.0638 (14)0.0187 (12)0.0329 (12)0.0094 (12)
O60.096 (2)0.0750 (18)0.146 (3)−0.0360 (16)0.092 (2)−0.0488 (19)
N10.0579 (15)0.0545 (15)0.0524 (15)−0.0013 (12)0.0314 (13)−0.0031 (12)
N20.0697 (18)0.0615 (17)0.088 (2)−0.0128 (14)0.0592 (17)−0.0233 (14)
N30.0554 (15)0.0481 (14)0.0540 (14)−0.0052 (11)0.0339 (13)−0.0116 (11)

Geometric parameters (Å, °)

S1—O21.404 (3)C15—H15A0.9300
S1—O11.432 (3)C16—C171.375 (7)
S1—N31.623 (3)C16—C201.516 (6)
S1—C11.786 (3)C17—C181.385 (6)
S2—O31.400 (3)C17—H17A0.9300
S2—O61.424 (3)C18—C191.510 (5)
S2—N21.640 (3)C19—H19A0.9600
S2—C131.773 (3)C19—H19B0.9600
C1—C21.403 (5)C19—H19C0.9600
C1—C61.408 (4)C20—H20A0.9600
C2—C31.390 (5)C20—H20B0.9600
C2—C91.526 (5)C20—H20C0.9600
C3—C41.374 (6)C21—H21A0.9600
C3—H3A0.9300C21—H21B0.9600
C4—C51.377 (6)C21—H21C0.9600
C4—C81.515 (5)C22—N21.473 (5)
C5—C61.379 (5)C22—C231.474 (5)
C5—H5A0.9300C22—H22A0.9700
C6—C71.503 (5)C22—H22B0.9700
C7—H7A0.9600C23—C241.513 (5)
C7—H7B0.9600C23—H23A0.9700
C7—H7C0.9600C23—H23B0.9700
C8—H8A0.9600C24—N11.453 (4)
C8—H8B0.9600C24—H24A0.9700
C8—H8C0.9600C24—H24B0.9700
C9—H9A0.9600C25—O41.199 (4)
C9—H9B0.9600C25—N11.402 (5)
C9—H9C0.9600C25—C261.479 (6)
C10—N31.465 (4)C26—C271.367 (5)
C10—C111.520 (5)C26—C311.386 (5)
C10—H10A0.9700C27—C281.375 (6)
C10—H10B0.9700C27—H27A0.9300
C11—C121.491 (6)C28—C291.371 (6)
C11—H11A0.9700C28—H28A0.9300
C11—H11B0.9700C29—C301.385 (5)
C12—N21.516 (4)C29—H29A0.9300
C12—H12A0.9700C30—C311.371 (5)
C12—H12B0.9700C30—H30A0.9300
C13—C181.402 (5)C31—C321.482 (5)
C13—C141.410 (5)C32—O51.205 (4)
C14—C151.393 (5)C32—N11.390 (4)
C14—C211.498 (5)N3—H3B0.8600
C15—C161.359 (7)
O2—S1—O1117.42 (17)C17—C16—C20120.9 (5)
O2—S1—N3107.70 (16)C16—C17—C18123.0 (4)
O1—S1—N3105.58 (15)C16—C17—H17A118.5
O2—S1—C1109.56 (15)C18—C17—H17A118.5
O1—S1—C1109.49 (15)C17—C18—C13117.6 (4)
N3—S1—C1106.49 (14)C17—C18—C19116.8 (4)
O3—S2—O6116.9 (2)C13—C18—C19125.6 (4)
O3—S2—N2110.94 (18)C18—C19—H19A109.5
O6—S2—N2106.63 (18)C18—C19—H19B109.5
O3—S2—C13108.23 (17)H19A—C19—H19B109.5
O6—S2—C13110.82 (17)C18—C19—H19C109.5
N2—S2—C13102.29 (16)H19A—C19—H19C109.5
C2—C1—C6120.5 (3)H19B—C19—H19C109.5
C2—C1—S1121.5 (2)C16—C20—H20A109.5
C6—C1—S1118.0 (2)C16—C20—H20B109.5
C3—C2—C1117.9 (3)H20A—C20—H20B109.5
C3—C2—C9116.3 (3)C16—C20—H20C109.5
C1—C2—C9125.8 (3)H20A—C20—H20C109.5
C4—C3—C2122.8 (4)H20B—C20—H20C109.5
C4—C3—H3A118.6C14—C21—H21A109.5
C2—C3—H3A118.6C14—C21—H21B109.5
C3—C4—C5117.7 (3)H21A—C21—H21B109.5
C3—C4—C8121.3 (4)C14—C21—H21C109.5
C5—C4—C8121.0 (4)H21A—C21—H21C109.5
C4—C5—C6123.0 (3)H21B—C21—H21C109.5
C4—C5—H5A118.5N2—C22—C23113.6 (3)
C6—C5—H5A118.5N2—C22—H22A108.9
C5—C6—C1118.1 (3)C23—C22—H22A108.9
C5—C6—C7116.9 (3)N2—C22—H22B108.9
C1—C6—C7125.1 (3)C23—C22—H22B108.9
C6—C7—H7A109.5H22A—C22—H22B107.7
C6—C7—H7B109.5C22—C23—C24113.9 (3)
H7A—C7—H7B109.5C22—C23—H23A108.8
C6—C7—H7C109.5C24—C23—H23A108.8
H7A—C7—H7C109.5C22—C23—H23B108.8
H7B—C7—H7C109.5C24—C23—H23B108.8
C4—C8—H8A109.5H23A—C23—H23B107.7
C4—C8—H8B109.5N1—C24—C23112.4 (3)
H8A—C8—H8B109.5N1—C24—H24A109.1
C4—C8—H8C109.5C23—C24—H24A109.1
H8A—C8—H8C109.5N1—C24—H24B109.1
H8B—C8—H8C109.5C23—C24—H24B109.1
C2—C9—H9A109.5H24A—C24—H24B107.9
C2—C9—H9B109.5O4—C25—N1123.8 (4)
H9A—C9—H9B109.5O4—C25—C26130.2 (4)
C2—C9—H9C109.5N1—C25—C26105.9 (3)
H9A—C9—H9C109.5C27—C26—C31121.3 (4)
H9B—C9—H9C109.5C27—C26—C25130.6 (3)
N3—C10—C11109.5 (3)C31—C26—C25108.0 (3)
N3—C10—H10A109.8C26—C27—C28117.7 (4)
C11—C10—H10A109.8C26—C27—H27A121.2
N3—C10—H10B109.8C28—C27—H27A121.2
C11—C10—H10B109.8C29—C28—C27121.6 (4)
H10A—C10—H10B108.2C29—C28—H28A119.2
C12—C11—C10109.3 (3)C27—C28—H28A119.2
C12—C11—H11A109.8C28—C29—C30120.6 (4)
C10—C11—H11A109.8C28—C29—H29A119.7
C12—C11—H11B109.8C30—C29—H29A119.7
C10—C11—H11B109.8C31—C30—C29118.0 (3)
H11A—C11—H11B108.3C31—C30—H30A121.0
C11—C12—N2113.7 (3)C29—C30—H30A121.0
C11—C12—H12A108.8C30—C31—C26120.8 (3)
N2—C12—H12A108.8C30—C31—C32130.9 (3)
C11—C12—H12B108.8C26—C31—C32108.4 (3)
N2—C12—H12B108.8O5—C32—N1124.9 (3)
H12A—C12—H12B107.7O5—C32—C31129.1 (3)
C18—C13—C14121.0 (3)N1—C32—C31105.9 (3)
C18—C13—S2116.5 (3)C32—N1—C25111.7 (3)
C14—C13—S2122.4 (3)C32—N1—C24125.1 (3)
C15—C14—C13117.0 (3)C25—N1—C24123.2 (3)
C15—C14—C21116.9 (3)C22—N2—C12119.1 (3)
C13—C14—C21126.0 (3)C22—N2—S2114.7 (2)
C16—C15—C14123.4 (4)C12—N2—S2118.8 (2)
C16—C15—H15A118.3C10—N3—S1118.2 (2)
C14—C15—H15A118.3C10—N3—H3B120.9
C15—C16—C17117.9 (4)S1—N3—H3B120.9
C15—C16—C20121.2 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3B···O5i0.862.533.192 (4)134

Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2835).

References

  • Bruker (2001). SAINT-Plus and SMART Bruker AXS, Inc., Madison, Wisconsin, USA.
  • Cullis, P. M., Green, R. E., Merson-Davies, L. & Travis, N. (1999). Chem. Biol.6, 717–729. [PubMed]
  • Seiler, N., Delcros, J.-G. & Moulinoux, J. P. (1996). Int. J. Biochem. Cell Biol.28, 843–861. [PubMed]
  • Sheldrick, G. M. (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Tsen, C., Iltis, M., Kaur, N., Bayer, C., Dekcros, J-G., von Kalm, L. & Phanstiel IV, O. (2008). J. Med. Chem.51, 324–330. [PubMed]

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