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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aCollege of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, People's Republic of China
*Correspondence e-mail: hgxywyx@126.com

(Received 2 November 2008; accepted 3 November 2008; online 8 November 2008)

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[Cullis, P. M., Green, R. E., Merson-Davies, L. & Travis, N. (1999). Chem. Biol. 6, 717-729.]); Seiler et al. (1996[Seiler, N., Delcros, J.-G. & Moulinoux, J. P. (1996). Int. J. Biochem. Cell Biol. 28, 843-861.]); Tsen et al. (2008[Tsen, C., Iltis, M., Kaur, N., Bayer, C., Dekcros, J-G., von Kalm, L. & Phanstiel IV, O. (2008). J. Med. Chem. 51, 324-330.]).

[Scheme 1]

Experimental

Crystal data
  • C32H39N3O6S2

  • Mr = 625.78

  • Monoclinic, C 2/c

  • 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[Sheldrick, G. M. (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.962, Tmax = 0.973

  • 17128 measured reflections

  • 6212 independent reflections

  • 4574 reflections with I > 2σ(I)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.069

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3B⋯O5i 0.86 2.53 3.192 (4) 134
Symmetry code: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT-Plus and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: PLATON.

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I). Displacement ellipsoids for the non-hydrogen atoms are drawn at the 50% probability level.
[Figure 2] 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.
2,2',4,4',6,6'-Hexamethyl-N-(3-phthalimidopropyl)-N,N'- (propane-1,3-diyl)dibenzenesulfonamide top
Crystal data top
C32H39N3O6S2F(000) = 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 = 2.4–28.1°
b = 9.9782 (8) ŵ = 0.22 mm1
c = 25.105 (2) ÅT = 296 K
β = 127.917 (1)°Block, colourless
V = 6332.1 (9) Å30.18 × 0.15 × 0.13 mm
Z = 8
Data collection top
Bruker SMART CCD
diffractometer
6212 independent reflections
Radiation source: fine-focus sealed tube4574 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω scansθmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 2539
Tmin = 0.962, Tmax = 0.973k = 1211
17128 measured reflectionsl = 3021
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)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.219H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.1169P)2 + 7.2057P]
where P = (Fo2 + 2Fc2)/3
6212 reflections(Δ/σ)max < 0.001
388 parametersΔρmax = 0.80 e Å3
44 restraintsΔρmin = 0.57 e Å3
Crystal data top
C32H39N3O6S2V = 6332.1 (9) Å3
Mr = 625.78Z = 8
Monoclinic, C2/cMo Kα radiation
a = 32.042 (3) ŵ = 0.22 mm1
b = 9.9782 (8) ÅT = 296 K
c = 25.105 (2) Å0.18 × 0.15 × 0.13 mm
β = 127.917 (1)°
Data collection top
Bruker SMART CCD
diffractometer
6212 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
4574 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.973Rint = 0.022
17128 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06944 restraints
wR(F2) = 0.219H-atom parameters constrained
S = 1.10Δρmax = 0.80 e Å3
6212 reflectionsΔρmin = 0.57 e Å3
388 parameters
Special details top

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*/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)
H8A0.10620.16450.40140.127*
H8B0.14390.17630.48030.127*
H8C0.16760.17000.44130.127*
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)
H17A0.02591.13060.57450.099*
C180.01232 (15)0.9547 (5)0.6035 (2)0.0743 (9)
C190.02361 (16)0.8980 (5)0.5329 (2)0.0848 (10)
H19A0.04940.96410.50280.127*
H19B0.04130.82010.53260.127*
H19C0.00300.87370.51850.127*
C200.0171 (2)1.2887 (5)0.6807 (3)0.1087 (13)
H20A0.04041.31530.72730.163*
H20B0.01881.29220.66460.163*
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) top
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, º) top
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, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···O5i0.862.533.192 (4)134
Symmetry code: (i) x+1/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC32H39N3O6S2
Mr625.78
Crystal system, space groupMonoclinic, C2/c
Temperature (K)296
a, b, c (Å)32.042 (3), 9.9782 (8), 25.105 (2)
β (°) 127.917 (1)
V3)6332.1 (9)
Z8
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.18 × 0.15 × 0.13
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.962, 0.973
No. of measured, independent and
observed [I > 2σ(I)] reflections
17128, 6212, 4574
Rint0.022
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.069, 0.219, 1.10
No. of reflections6212
No. of parameters388
No. of restraints44
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.80, 0.57

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···O5i0.862.533.192 (4)134
Symmetry code: (i) x+1/2, y1/2, z+3/2.
 

Acknowledgements

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

References

First citationBruker (2001). SAINT-Plus and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCullis, P. M., Green, R. E., Merson-Davies, L. & Travis, N. (1999). Chem. Biol. 6, 717–729.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSeiler, N., Delcros, J.-G. & Moulinoux, J. P. (1996). Int. J. Biochem. Cell Biol. 28, 843–861.  CrossRef CAS PubMed Web of Science Google Scholar
First citationSheldrick, G. M. (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTsen, C., Iltis, M., Kaur, N., Bayer, C., Dekcros, J-G., von Kalm, L. & Phanstiel IV, O. (2008). J. Med. Chem. 51, 324–330.  Web of Science CrossRef PubMed CAS 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
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds