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

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ISSN: 2056-9890

(5′′E)-1′′-Benzyl-1′-methyl-5′′-[4-(methyl­sulfan­yl)benzyl­­idene]-4′-[4-(methyl­sulfan­yl)phen­yl]di­spiro­[indoline-3,2′-pyrrolidine-3′,3′′-piperidine]-2,4′′-dione di­chloro­methane solvate

aSchool of Environmental Science and Engineering, Hebei University of Science and Technology. 050018 Shijiazhuang, Hebei province, People's Republic of China
*Correspondence e-mail: houyjhb@163.com

(Received 27 November 2009; accepted 20 December 2009; online 24 December 2009)

In the title compound, C38H36N3O2S2·CH2Cl2, the 2-oxindole ring is almost planar (r.m.s. deviation = 0.032 Å), the pyrrolidine ring adopts a twist conformation and the piperidone ring exists as a chair. Three short C—H⋯O intra­molecular contacts occur. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯N inter­actions. The dichloro­methane solvent mol­ecule is disordered over two orientations in a 0.765 (11):0.235 (11) ratio.

Related literature

For background to dispiro ring systems, see: Kobayashi et al. (1991[Kobayashi, J., Tsuda, M., Agemi, K. & Vacelet, J. (1991). Tetrahedron, 47, 6617-6622.]).

[Scheme 1]

Experimental

Crystal data
  • C38H36N3O2S2·CH2Cl2

  • Mr = 715.74

  • Monoclinic, C 2/c

  • a = 36.456 (7) Å

  • b = 8.6164 (17) Å

  • c = 26.184 (5) Å

  • β = 119.58 (3)°

  • V = 7153 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.34 mm−1

  • T = 113 K

  • 0.20 × 0.18 × 0.12 mm

Data collection
  • Rigaku Saturn CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.936, Tmax = 0.961

  • 20568 measured reflections

  • 6263 independent reflections

  • 2890 reflections with I > 2σ(I)

  • Rint = 0.116

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.154

  • S = 1.01

  • 6263 reflections

  • 455 parameters

  • 40 restraints

  • H-atom parameters constrained

  • Δρmax = 0.44 e Å−3

  • Δρmin = −0.46 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C1—H1A⋯O2 0.97 2.53 3.149 (5) 122
C7—H7B⋯O2 0.97 2.37 2.971 (5) 119
C10—H10⋯O1 0.93 2.57 3.220 (5) 127
C39—H39A⋯N3 0.97 2.44 3.405 (10) 175
C39—H39B⋯O1 0.97 2.53 3.140 (7) 121

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

In this paper, the structure of the title compound, (I), is reported. The molecular structure of (I) is illustrated in Fig. 1. There exists a dispiro rings in the molecule which was consist of a 2-oxindole ring, a pyrrolidine ring and a piperidone rings. The pyrrolidine ring is not planar, with twist conformations. 2-oxindole ring (C15/N2/C14/C13/C12/C11/C10/C9/C8) is nearly planar that the mean deviation from this plane is 0.0148 (3)%A.

The piperidone ring has the usual chair conformation. There exist intermolecular O—H—N hydrogen bonds.

Related literature top

For background to dispiro ring systems, see: Kobayashi et al. (1991).

Experimental top

A mixture of 1-benzyl-3,5-bis-(4-methylsulfanyl-benzylidene)-piperidin-4-one (2 mmol), isatin (2 mmol) and sarcosine (2 mmol) were refluxed in methanol (80 ml) until the disapperence of the starting material as evidenced by the TLC. After the reaction was over the solvent was removed in vacuo and the residue was separated by column chromatography (silica gel, petroleum ether/ethyl acetate = 5:1) to give the title compound. 20 mg of the title compound was dissolved in 15 ml dichloromethane; the solution was kept at room temperature for 15 d by natural evaporation to give colourless blocks of (I).

Refinement top

All H atoms were fixed geometrically and treated as riding with C—H = 0.96Å (methyl), 0.97Å (methylene), 0.98Å (methine) with Uiso(H) = 1.2Ueq(C) or Uiso(H)= 1.5Ueq(methine).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids
(5''E)-1''-Benzyl-1'-methyl-5''-[4-(methylsulfanyl)benzylidene]-4'-[4- (methylsulfanyl)phenyl]dispiro[indoline-3,2'-pyrrolidine-3',3''- piperidine]-2,4''-dione dichloromethane solvate top
Crystal data top
C38H36N3O2S2·CH2Cl2F(000) = 3000
Mr = 715.74Dx = 1.329 Mg m3
Monoclinic, C2/cMelting point: 473 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 36.456 (7) ÅCell parameters from 8719 reflections
b = 8.6164 (17) Åθ = 1.6–27.9°
c = 26.184 (5) ŵ = 0.34 mm1
β = 119.58 (3)°T = 113 K
V = 7153 (2) Å3Block, colourless
Z = 80.20 × 0.18 × 0.12 mm
Data collection top
Rigaku Saturn CCD
diffractometer
6263 independent reflections
Radiation source: rotating anode2890 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.116
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 2.3°
ω and ϕ scansh = 3643
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1010
Tmin = 0.936, Tmax = 0.961l = 3130
20568 measured reflections
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.028P)2]
where P = (Fo2 + 2Fc2)/3
6263 reflections(Δ/σ)max = 0.001
455 parametersΔρmax = 0.44 e Å3
40 restraintsΔρmin = 0.46 e Å3
Crystal data top
C38H36N3O2S2·CH2Cl2V = 7153 (2) Å3
Mr = 715.74Z = 8
Monoclinic, C2/cMo Kα radiation
a = 36.456 (7) ŵ = 0.34 mm1
b = 8.6164 (17) ÅT = 113 K
c = 26.184 (5) Å0.20 × 0.18 × 0.12 mm
β = 119.58 (3)°
Data collection top
Rigaku Saturn CCD
diffractometer
6263 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
2890 reflections with I > 2σ(I)
Tmin = 0.936, Tmax = 0.961Rint = 0.116
20568 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05940 restraints
wR(F2) = 0.154H-atom parameters constrained
S = 1.01Δρmax = 0.44 e Å3
6263 reflectionsΔρmin = 0.46 e Å3
455 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*/UeqOcc. (<1)
S10.81245 (4)0.42806 (12)0.32967 (5)0.0300 (3)
S21.03858 (4)0.26067 (12)0.01917 (5)0.0282 (3)
O10.93859 (8)0.1218 (3)0.23595 (11)0.0217 (7)
O20.77000 (8)0.1837 (3)0.07939 (11)0.0206 (6)
N10.84168 (10)0.0525 (3)0.08359 (13)0.0167 (7)
N20.80248 (10)0.2974 (3)0.03269 (13)0.0161 (8)
N30.84549 (10)0.3613 (3)0.17922 (13)0.0162 (7)
C10.83077 (13)0.2676 (4)0.21221 (16)0.0197 (9)
H1A0.80140.23840.18790.024*
H1B0.83420.32250.24660.024*
C20.85950 (12)0.1269 (4)0.22927 (17)0.0188 (9)
H20.88730.16050.26040.023*
C30.86374 (12)0.0969 (4)0.17302 (15)0.0123 (8)
C40.90973 (12)0.0694 (4)0.18967 (16)0.0161 (9)
C50.91820 (12)0.0144 (4)0.14716 (16)0.0148 (9)
C60.88378 (11)0.1081 (4)0.09815 (16)0.0178 (9)
H6A0.88700.10160.06360.021*
H6B0.88660.21620.10990.021*
C70.83915 (12)0.0466 (4)0.13777 (15)0.0163 (9)
H7A0.85120.14000.16070.020*
H7B0.80990.03950.12840.020*
C80.84714 (12)0.2525 (4)0.13602 (16)0.0154 (9)
C90.87097 (11)0.3202 (4)0.10800 (16)0.0151 (9)
C100.91286 (12)0.3682 (4)0.13121 (17)0.0194 (9)
H100.93180.35590.17110.023*
C110.92606 (12)0.4327 (4)0.09561 (17)0.0211 (10)
H110.95390.46510.11160.025*
C120.89836 (13)0.4514 (4)0.03508 (18)0.0246 (10)
H120.90810.49240.01110.029*
C130.85601 (12)0.4080 (4)0.01113 (17)0.0177 (9)
H130.83700.42180.02860.021*
C140.84364 (12)0.3449 (4)0.04796 (16)0.0163 (9)
C150.80162 (12)0.2343 (4)0.08046 (16)0.0192 (9)
C160.82163 (14)0.5041 (4)0.15488 (17)0.0275 (11)
H16A0.79280.47900.12750.041*
H16B0.83360.56080.13500.041*
H16C0.82280.56640.18610.041*
C170.84726 (12)0.0104 (4)0.25245 (15)0.0145 (9)
C180.80632 (12)0.0352 (5)0.24449 (16)0.0223 (10)
H180.78510.03640.22300.027*
C190.79734 (13)0.1614 (5)0.26757 (17)0.0234 (10)
H190.77000.17450.26070.028*
C200.82776 (13)0.2718 (4)0.30111 (16)0.0203 (10)
C210.86876 (13)0.2481 (4)0.31048 (17)0.0233 (10)
H210.89000.31870.33290.028*
C220.87787 (13)0.1194 (5)0.28639 (17)0.0247 (10)
H220.90520.10600.29320.030*
C230.86044 (12)0.5343 (5)0.37319 (17)0.0286 (11)
H23A0.86930.58190.34790.043*
H23B0.85570.61300.39520.043*
H23C0.88200.46460.39970.043*
C240.95764 (12)0.0014 (4)0.15326 (17)0.0207 (10)
H240.97590.06370.18460.025*
C250.97545 (12)0.0613 (4)0.11979 (16)0.0165 (9)
C261.00906 (12)0.0163 (4)0.11886 (17)0.0233 (10)
H261.01880.10810.14000.028*
C271.02810 (12)0.0368 (5)0.08835 (18)0.0254 (10)
H271.04960.02100.08830.031*
C281.01570 (12)0.1768 (4)0.05726 (17)0.0226 (10)
C290.98184 (13)0.2554 (4)0.05714 (18)0.0249 (10)
H290.97230.34720.03590.030*
C300.96232 (13)0.2024 (4)0.08701 (18)0.0232 (10)
H300.94020.25900.08590.028*
C311.07740 (13)0.1205 (4)0.02636 (19)0.0291 (11)
H31A1.06370.02380.00930.044*
H31B1.09180.15760.00640.044*
H31C1.09740.10520.06720.044*
C320.80877 (13)0.1550 (4)0.03998 (16)0.0247 (10)
H32A0.78200.12890.03740.030*
H32B0.81540.26140.05370.030*
C330.80392 (12)0.1451 (4)0.02036 (16)0.0191 (9)
C340.78570 (11)0.2681 (4)0.05875 (17)0.0180 (9)
H340.77920.35890.04570.022*
C350.77693 (13)0.2570 (5)0.11688 (18)0.0288 (11)
H350.76460.34020.14230.035*
C360.78647 (13)0.1237 (5)0.13671 (18)0.0306 (11)
H360.78000.11600.17570.037*
C370.80560 (13)0.0015 (5)0.09880 (18)0.0288 (11)
H370.81260.08800.11190.035*
C380.81437 (13)0.0121 (5)0.04127 (17)0.0244 (10)
H380.82750.07060.01590.029*
Cl10.95562 (15)0.6560 (5)0.26917 (14)0.0621 (10)0.765 (11)
C390.9453 (3)0.4623 (7)0.2825 (3)0.050 (2)0.765 (11)
H39A0.91630.43620.25460.060*0.765 (11)
H39B0.96340.39170.27620.060*0.765 (11)
Cl1'0.9728 (4)0.5901 (17)0.2710 (4)0.060 (3)0.235 (11)
C39'0.9325 (4)0.508 (4)0.2821 (6)0.049 (5)0.235 (11)
H39C0.91150.58680.27500.058*0.235 (11)
H39D0.91880.42460.25430.058*0.235 (11)
Cl20.95372 (4)0.43615 (14)0.35449 (6)0.0482 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0261 (7)0.0307 (6)0.0351 (7)0.0029 (6)0.0166 (6)0.0082 (6)
S20.0301 (7)0.0283 (6)0.0334 (7)0.0046 (5)0.0213 (6)0.0022 (6)
O10.0125 (15)0.0322 (16)0.0118 (15)0.0005 (13)0.0006 (13)0.0042 (13)
O20.0099 (15)0.0301 (15)0.0189 (16)0.0067 (13)0.0049 (13)0.0066 (13)
N10.0142 (18)0.0185 (16)0.0123 (18)0.0033 (15)0.0027 (15)0.0038 (15)
N20.0154 (18)0.0216 (17)0.0151 (18)0.0049 (15)0.0104 (15)0.0053 (15)
N30.0218 (19)0.0154 (16)0.0154 (18)0.0015 (15)0.0122 (16)0.0002 (15)
C10.028 (3)0.018 (2)0.017 (2)0.0012 (19)0.013 (2)0.0018 (18)
C20.015 (2)0.024 (2)0.015 (2)0.0008 (19)0.0060 (19)0.0012 (19)
C30.014 (2)0.0155 (19)0.009 (2)0.0007 (18)0.0065 (17)0.0044 (17)
C40.018 (2)0.0125 (19)0.015 (2)0.0009 (18)0.007 (2)0.0051 (18)
C50.012 (2)0.022 (2)0.013 (2)0.0010 (18)0.0078 (18)0.0014 (18)
C60.021 (2)0.017 (2)0.019 (2)0.0050 (19)0.012 (2)0.0017 (18)
C70.017 (2)0.025 (2)0.010 (2)0.0001 (19)0.0094 (18)0.0006 (18)
C80.013 (2)0.022 (2)0.011 (2)0.0007 (19)0.0057 (18)0.0002 (18)
C90.013 (2)0.0135 (19)0.017 (2)0.0002 (18)0.0057 (19)0.0039 (18)
C100.016 (2)0.013 (2)0.019 (2)0.0025 (18)0.0008 (19)0.0029 (18)
C110.013 (2)0.019 (2)0.030 (3)0.0009 (19)0.009 (2)0.002 (2)
C120.029 (3)0.019 (2)0.029 (3)0.003 (2)0.017 (2)0.002 (2)
C130.018 (2)0.021 (2)0.015 (2)0.0021 (19)0.0090 (19)0.0025 (18)
C140.015 (2)0.016 (2)0.013 (2)0.0060 (18)0.0032 (18)0.0002 (18)
C150.014 (2)0.026 (2)0.011 (2)0.004 (2)0.0020 (18)0.0010 (19)
C160.041 (3)0.028 (2)0.022 (3)0.008 (2)0.022 (2)0.006 (2)
C170.016 (2)0.0167 (19)0.008 (2)0.0033 (18)0.0042 (18)0.0037 (17)
C180.019 (2)0.032 (2)0.011 (2)0.002 (2)0.0042 (19)0.001 (2)
C190.017 (2)0.029 (2)0.023 (3)0.001 (2)0.010 (2)0.008 (2)
C200.025 (2)0.029 (2)0.011 (2)0.007 (2)0.0120 (19)0.0068 (19)
C210.018 (2)0.026 (2)0.024 (2)0.004 (2)0.009 (2)0.006 (2)
C220.016 (2)0.038 (3)0.017 (2)0.006 (2)0.006 (2)0.003 (2)
C230.031 (3)0.036 (3)0.024 (3)0.007 (2)0.018 (2)0.003 (2)
C240.017 (2)0.017 (2)0.017 (2)0.0038 (19)0.0003 (19)0.0012 (19)
C250.015 (2)0.018 (2)0.016 (2)0.0048 (18)0.0077 (19)0.0028 (18)
C260.018 (2)0.024 (2)0.023 (2)0.001 (2)0.006 (2)0.004 (2)
C270.014 (2)0.029 (2)0.029 (3)0.002 (2)0.007 (2)0.002 (2)
C280.019 (2)0.023 (2)0.022 (2)0.002 (2)0.008 (2)0.007 (2)
C290.024 (3)0.022 (2)0.027 (3)0.000 (2)0.011 (2)0.001 (2)
C300.019 (2)0.017 (2)0.033 (3)0.0006 (19)0.013 (2)0.002 (2)
C310.038 (3)0.027 (2)0.042 (3)0.007 (2)0.035 (3)0.005 (2)
C320.020 (2)0.029 (2)0.019 (2)0.011 (2)0.004 (2)0.004 (2)
C330.014 (2)0.030 (2)0.012 (2)0.001 (2)0.0049 (19)0.000 (2)
C340.014 (2)0.017 (2)0.024 (2)0.0007 (18)0.0102 (19)0.0014 (19)
C350.025 (3)0.037 (3)0.020 (2)0.000 (2)0.008 (2)0.011 (2)
C360.034 (3)0.033 (3)0.019 (3)0.001 (2)0.009 (2)0.002 (2)
C370.030 (3)0.034 (2)0.025 (3)0.002 (2)0.015 (2)0.005 (2)
C380.027 (2)0.028 (2)0.014 (2)0.009 (2)0.006 (2)0.009 (2)
Cl10.062 (2)0.0615 (18)0.0748 (16)0.0259 (16)0.0424 (15)0.0276 (14)
C390.034 (5)0.037 (4)0.050 (4)0.012 (3)0.001 (3)0.027 (3)
Cl1'0.054 (5)0.069 (6)0.040 (4)0.019 (4)0.010 (3)0.005 (4)
C39'0.040 (9)0.053 (9)0.047 (8)0.001 (8)0.017 (7)0.017 (8)
Cl20.0323 (7)0.0441 (7)0.0626 (9)0.0007 (6)0.0191 (7)0.0107 (7)
Geometric parameters (Å, º) top
S1—C201.760 (4)C18—H180.9300
S1—C231.797 (4)C19—C201.394 (5)
S2—C281.742 (4)C19—H190.9300
S2—C311.799 (4)C20—C211.405 (5)
O1—C41.233 (4)C21—C221.394 (5)
O2—C151.220 (4)C21—H210.9300
N1—C61.467 (4)C22—H220.9300
N1—C71.467 (4)C23—H23A0.9600
N1—C321.474 (4)C23—H23B0.9600
N2—C151.378 (4)C23—H23C0.9600
N2—C141.409 (4)C24—C251.429 (5)
N3—C161.459 (4)C24—H240.9300
N3—C11.464 (4)C25—C261.406 (5)
N3—C81.493 (4)C25—C301.428 (5)
C1—C21.518 (5)C26—C271.370 (5)
C1—H1A0.9700C26—H260.9300
C1—H1B0.9700C27—C281.399 (5)
C2—C171.495 (5)C27—H270.9300
C2—C31.576 (5)C28—C291.406 (5)
C2—H20.9800C29—C301.370 (5)
C3—C41.528 (5)C29—H290.9300
C3—C71.539 (5)C30—H300.9300
C3—C81.588 (5)C31—H31A0.9600
C4—C51.482 (5)C31—H31B0.9600
C5—C241.373 (5)C31—H31C0.9600
C5—C61.511 (5)C32—C331.503 (5)
C6—H6A0.9700C32—H32A0.9700
C6—H6B0.9700C32—H32B0.9700
C7—H7A0.9700C33—C341.384 (5)
C7—H7B0.9700C33—C381.402 (5)
C8—C91.504 (5)C34—C351.395 (5)
C8—C151.585 (5)C34—H340.9300
C9—C101.399 (5)C35—C361.374 (5)
C9—C141.401 (5)C35—H350.9300
C10—C111.361 (5)C36—C371.377 (5)
C10—H100.9300C36—H360.9300
C11—C121.406 (5)C37—C381.380 (5)
C11—H110.9300C37—H370.9300
C12—C131.400 (5)C38—H380.9300
C12—H120.9300Cl1—C391.783 (6)
C13—C141.363 (5)C39—Cl21.767 (6)
C13—H130.9300C39—H39A0.9700
C16—H16A0.9600C39—H39B0.9700
C16—H16B0.9600Cl1'—C39'1.778 (10)
C16—H16C0.9600C39'—Cl21.770 (10)
C17—C221.392 (5)C39'—H39C0.9700
C17—C181.418 (5)C39'—H39D0.9700
C18—C191.360 (5)
C20—S1—C23104.20 (19)C17—C18—H18119.3
C28—S2—C31103.65 (18)C18—C19—C20122.3 (4)
C6—N1—C7108.5 (3)C18—C19—H19118.9
C6—N1—C32110.6 (3)C20—C19—H19118.9
C7—N1—C32110.7 (3)C19—C20—C21117.2 (4)
C15—N2—C14110.8 (3)C19—C20—S1118.0 (3)
C16—N3—C1114.2 (3)C21—C20—S1124.8 (3)
C16—N3—C8115.9 (3)C22—C21—C20120.5 (4)
C1—N3—C8105.3 (3)C22—C21—H21119.8
N3—C1—C2102.3 (3)C20—C21—H21119.8
N3—C1—H1A111.3C17—C22—C21122.0 (4)
C2—C1—H1A111.3C17—C22—H22119.0
N3—C1—H1B111.3C21—C22—H22119.0
C2—C1—H1B111.3S1—C23—H23A109.5
H1A—C1—H1B109.2S1—C23—H23B109.5
C17—C2—C1116.8 (3)H23A—C23—H23B109.5
C17—C2—C3115.9 (3)S1—C23—H23C109.5
C1—C2—C3103.1 (3)H23A—C23—H23C109.5
C17—C2—H2106.8H23B—C23—H23C109.5
C1—C2—H2106.8C5—C24—C25131.1 (4)
C3—C2—H2106.8C5—C24—H24114.4
C4—C3—C7106.2 (3)C25—C24—H24114.4
C4—C3—C2111.0 (3)C26—C25—C30115.5 (3)
C7—C3—C2113.3 (3)C26—C25—C24119.6 (3)
C4—C3—C8109.8 (3)C30—C25—C24124.9 (4)
C7—C3—C8112.2 (3)C27—C26—C25123.2 (4)
C2—C3—C8104.4 (3)C27—C26—H26118.4
O1—C4—C5121.6 (3)C25—C26—H26118.4
O1—C4—C3120.5 (3)C26—C27—C28121.1 (4)
C5—C4—C3117.9 (3)C26—C27—H27119.5
C24—C5—C4117.3 (4)C28—C27—H27119.5
C24—C5—C6122.3 (3)C27—C28—C29116.6 (4)
C4—C5—C6120.3 (3)C27—C28—S2125.6 (3)
N1—C6—C5111.7 (3)C29—C28—S2117.8 (3)
N1—C6—H6A109.3C30—C29—C28122.7 (4)
C5—C6—H6A109.3C30—C29—H29118.6
N1—C6—H6B109.3C28—C29—H29118.6
C5—C6—H6B109.3C29—C30—C25120.9 (4)
H6A—C6—H6B107.9C29—C30—H30119.6
N1—C7—C3108.1 (3)C25—C30—H30119.6
N1—C7—H7A110.1S2—C31—H31A109.5
C3—C7—H7A110.1S2—C31—H31B109.5
N1—C7—H7B110.1H31A—C31—H31B109.5
C3—C7—H7B110.1S2—C31—H31C109.5
H7A—C7—H7B108.4H31A—C31—H31C109.5
N3—C8—C9112.0 (3)H31B—C31—H31C109.5
N3—C8—C15110.0 (3)N1—C32—C33114.1 (3)
C9—C8—C15100.7 (3)N1—C32—H32A108.7
N3—C8—C3102.3 (3)C33—C32—H32A108.7
C9—C8—C3119.1 (3)N1—C32—H32B108.7
C15—C8—C3112.8 (3)C33—C32—H32B108.7
C10—C9—C14117.5 (3)H32A—C32—H32B107.6
C10—C9—C8132.2 (3)C34—C33—C38117.9 (3)
C14—C9—C8110.1 (3)C34—C33—C32119.0 (3)
C11—C10—C9120.2 (4)C38—C33—C32122.9 (4)
C11—C10—H10119.9C33—C34—C35120.6 (4)
C9—C10—H10119.9C33—C34—H34119.7
C10—C11—C12121.3 (4)C35—C34—H34119.7
C10—C11—H11119.4C36—C35—C34120.3 (4)
C12—C11—H11119.4C36—C35—H35119.8
C13—C12—C11119.6 (4)C34—C35—H35119.8
C13—C12—H12120.2C35—C36—C37119.9 (4)
C11—C12—H12120.2C35—C36—H36120.0
C14—C13—C12117.8 (4)C37—C36—H36120.0
C14—C13—H13121.1C36—C37—C38119.9 (4)
C12—C13—H13121.1C36—C37—H37120.1
C13—C14—C9123.6 (4)C38—C37—H37120.1
C13—C14—N2126.4 (3)C37—C38—C33121.3 (4)
C9—C14—N2110.0 (3)C37—C38—H38119.4
O2—C15—N2124.4 (4)C33—C38—H38119.4
O2—C15—C8127.3 (3)Cl2—C39—Cl1112.7 (3)
N2—C15—C8108.2 (3)Cl2—C39—H39A109.0
N3—C16—H16A109.5Cl1—C39—H39A109.0
N3—C16—H16B109.5Cl2—C39—H39B109.0
H16A—C16—H16B109.5Cl1—C39—H39B109.0
N3—C16—H16C109.5H39A—C39—H39B107.8
H16A—C16—H16C109.5Cl2—C39'—Cl1'110.8 (8)
H16B—C16—H16C109.5Cl2—C39'—H39C109.5
C22—C17—C18116.5 (3)Cl1'—C39'—H39C109.5
C22—C17—C2119.2 (3)Cl2—C39'—H39D109.5
C18—C17—C2124.3 (4)Cl1'—C39'—H39D109.5
C19—C18—C17121.5 (4)H39C—C39'—H39D108.1
C19—C18—H18119.3C39—Cl2—C39'19.7 (8)
C16—N3—C1—C2177.5 (3)C10—C9—C14—N2177.0 (3)
C8—N3—C1—C249.3 (3)C8—C9—C14—N20.4 (4)
N3—C1—C2—C17166.9 (3)C15—N2—C14—C13178.1 (3)
N3—C1—C2—C338.6 (3)C15—N2—C14—C92.8 (4)
C17—C2—C3—C497.5 (4)C14—N2—C15—O2179.9 (3)
C1—C2—C3—C4133.6 (3)C14—N2—C15—C84.6 (4)
C17—C2—C3—C721.8 (5)N3—C8—C15—O261.5 (5)
C1—C2—C3—C7107.1 (3)C9—C8—C15—O2179.9 (4)
C17—C2—C3—C8144.2 (3)C3—C8—C15—O252.0 (5)
C1—C2—C3—C815.3 (4)N3—C8—C15—N2113.8 (3)
C7—C3—C4—O1148.3 (3)C9—C8—C15—N24.5 (4)
C2—C3—C4—O124.8 (5)C3—C8—C15—N2132.6 (3)
C8—C3—C4—O190.1 (4)C1—C2—C17—C22158.7 (3)
C7—C3—C4—C534.9 (4)C3—C2—C17—C2279.4 (4)
C2—C3—C4—C5158.4 (3)C1—C2—C17—C1818.3 (5)
C8—C3—C4—C586.7 (4)C3—C2—C17—C18103.5 (4)
O1—C4—C5—C2416.0 (5)C22—C17—C18—C191.8 (5)
C3—C4—C5—C24160.8 (3)C2—C17—C18—C19178.9 (3)
O1—C4—C5—C6166.1 (3)C17—C18—C19—C201.2 (6)
C3—C4—C5—C617.1 (5)C18—C19—C20—C210.0 (6)
C7—N1—C6—C552.7 (4)C18—C19—C20—S1178.9 (3)
C32—N1—C6—C5174.3 (3)C23—S1—C20—C19176.4 (3)
C24—C5—C6—N1153.3 (3)C23—S1—C20—C212.4 (4)
C4—C5—C6—N124.5 (5)C19—C20—C21—C220.5 (6)
C6—N1—C7—C376.1 (3)S1—C20—C21—C22179.3 (3)
C32—N1—C7—C3162.3 (3)C18—C17—C22—C211.2 (5)
C4—C3—C7—N164.0 (4)C2—C17—C22—C21178.5 (3)
C2—C3—C7—N1173.9 (3)C20—C21—C22—C170.1 (6)
C8—C3—C7—N156.0 (4)C4—C5—C24—C25179.2 (3)
C16—N3—C8—C965.9 (4)C6—C5—C24—C251.4 (6)
C1—N3—C8—C9166.9 (3)C5—C24—C25—C26154.6 (4)
C16—N3—C8—C1545.2 (4)C5—C24—C25—C3026.8 (7)
C1—N3—C8—C1582.0 (3)C30—C25—C26—C270.7 (6)
C16—N3—C8—C3165.3 (3)C24—C25—C26—C27179.4 (4)
C1—N3—C8—C338.1 (3)C25—C26—C27—C282.0 (6)
C4—C3—C8—N3106.3 (3)C26—C27—C28—C292.5 (6)
C7—C3—C8—N3135.8 (3)C26—C27—C28—S2177.4 (3)
C2—C3—C8—N312.8 (3)C31—S2—C28—C273.5 (4)
C4—C3—C8—C917.9 (4)C31—S2—C28—C29176.5 (3)
C7—C3—C8—C9100.0 (4)C27—C28—C29—C301.9 (6)
C2—C3—C8—C9136.9 (3)S2—C28—C29—C30178.1 (3)
C4—C3—C8—C15135.6 (3)C28—C29—C30—C250.6 (6)
C7—C3—C8—C1517.7 (4)C26—C25—C30—C290.0 (6)
C2—C3—C8—C15105.3 (3)C24—C25—C30—C29178.6 (4)
N3—C8—C9—C1061.9 (5)C6—N1—C32—C3370.4 (4)
C15—C8—C9—C10178.8 (4)C7—N1—C32—C33169.3 (3)
C3—C8—C9—C1057.4 (5)N1—C32—C33—C34157.8 (3)
N3—C8—C9—C14114.0 (3)N1—C32—C33—C3826.7 (5)
C15—C8—C9—C142.9 (4)C38—C33—C34—C352.0 (6)
C3—C8—C9—C14126.7 (3)C32—C33—C34—C35173.7 (4)
C14—C9—C10—C111.5 (5)C33—C34—C35—C360.3 (6)
C8—C9—C10—C11177.2 (4)C34—C35—C36—C371.4 (6)
C9—C10—C11—C120.6 (6)C35—C36—C37—C381.3 (6)
C10—C11—C12—C132.3 (6)C36—C37—C38—C330.4 (6)
C11—C12—C13—C141.7 (5)C34—C33—C38—C372.1 (6)
C12—C13—C14—C90.5 (6)C32—C33—C38—C37173.4 (4)
C12—C13—C14—N2178.4 (3)Cl1—C39—Cl2—C39'61 (2)
C10—C9—C14—C132.1 (5)Cl1'—C39'—Cl2—C3958.0 (14)
C8—C9—C14—C13178.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O20.972.533.149 (5)122
C7—H7B···O20.972.372.971 (5)119
C10—H10···O10.932.573.220 (5)127
C39—H39A···N30.972.443.405 (10)175
C39—H39B···O10.972.533.140 (7)121

Experimental details

Crystal data
Chemical formulaC38H36N3O2S2·CH2Cl2
Mr715.74
Crystal system, space groupMonoclinic, C2/c
Temperature (K)113
a, b, c (Å)36.456 (7), 8.6164 (17), 26.184 (5)
β (°) 119.58 (3)
V3)7153 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.34
Crystal size (mm)0.20 × 0.18 × 0.12
Data collection
DiffractometerRigaku Saturn CCD
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.936, 0.961
No. of measured, independent and
observed [I > 2σ(I)] reflections
20568, 6263, 2890
Rint0.116
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.154, 1.01
No. of reflections6263
No. of parameters455
No. of restraints40
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.44, 0.46

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O20.972.533.149 (5)122
C7—H7B···O20.972.372.971 (5)119
C10—H10···O10.932.573.220 (5)127
C39—H39A···N30.972.443.405 (10)175
C39—H39B···O10.972.533.140 (7)121
 

References

First citationKobayashi, J., Tsuda, M., Agemi, K. & Vacelet, J. (1991). Tetrahedron, 47, 6617–6622.  CrossRef CAS Web of Science
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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