(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

Hou, Y.

doi:10.1107/S1600536809054774

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o244

doi:10.1107/S1600536809054774

Open

access

(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

Yongjiang Hou ^a ^*

^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 ).

Experimental

Crystal data

C₃₈H₃₆N₃O₂S₂·CH₂Cl₂
M_r = 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 ) T_min = 0.936, T_max = 0.961
20568 measured reflections
6263 independent reflections
2890 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809054774/hb5259sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809054774/hb5259Isup2.hkl

checkCIF report

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).

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

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·CH₂Cl₂	F(000) = 3000
M_r = 715.74	D_x = 1.329 Mg m⁻³
Monoclinic, C2/c	Melting point: 473 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 36.456 (7) Å	Cell parameters from 8719 reflections
b = 8.6164 (17) Å	θ = 1.6–27.9°
c = 26.184 (5) Å	µ = 0.34 mm⁻¹
β = 119.58 (3)°	T = 113 K
V = 7153 (2) Å³	Block, colourless
Z = 8	0.20 × 0.18 × 0.12 mm

Data collection top

Rigaku Saturn CCD diffractometer	6263 independent reflections
Radiation source: rotating anode	2890 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.116
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 2.3°
ω and ϕ scans	h = −36→43
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
T_min = 0.936, T_max = 0.961	l = −31→30
20568 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.028P)²] where P = (F_o² + 2F_c²)/3
6263 reflections	(Δ/σ)_max = 0.001
455 parameters	Δρ_max = 0.44 e Å⁻³
40 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₃₈H₃₆N₃O₂S₂·CH₂Cl₂	V = 7153 (2) Å³
M_r = 715.74	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 36.456 (7) Å	µ = 0.34 mm⁻¹
b = 8.6164 (17) Å	T = 113 K
c = 26.184 (5) Å	0.20 × 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)
T_min = 0.936, T_max = 0.961	R_int = 0.116
20568 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	40 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.01	Δρ_max = 0.44 e Å⁻³
6263 reflections	Δρ_min = −0.46 e Å⁻³
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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.81245 (4)	−0.42806 (12)	0.32967 (5)	0.0300 (3)
S2	1.03858 (4)	−0.26067 (12)	0.01917 (5)	0.0282 (3)
O1	0.93859 (8)	0.1218 (3)	0.23595 (11)	0.0217 (7)
O2	0.77000 (8)	0.1837 (3)	0.07939 (11)	0.0206 (6)
N1	0.84168 (10)	−0.0525 (3)	0.08359 (13)	0.0167 (7)
N2	0.80248 (10)	0.2974 (3)	0.03269 (13)	0.0161 (8)
N3	0.84549 (10)	0.3613 (3)	0.17922 (13)	0.0162 (7)
C1	0.83077 (13)	0.2676 (4)	0.21221 (16)	0.0197 (9)
H1A	0.8014	0.2384	0.1879	0.024*
H1B	0.8342	0.3225	0.2466	0.024*
C2	0.85950 (12)	0.1269 (4)	0.22927 (17)	0.0188 (9)
H2	0.8873	0.1605	0.2604	0.023*
C3	0.86374 (12)	0.0969 (4)	0.17302 (15)	0.0123 (8)
C4	0.90973 (12)	0.0694 (4)	0.18967 (16)	0.0161 (9)
C5	0.91820 (12)	−0.0144 (4)	0.14716 (16)	0.0148 (9)
C6	0.88378 (11)	−0.1081 (4)	0.09815 (16)	0.0178 (9)
H6A	0.8870	−0.1016	0.0636	0.021*
H6B	0.8866	−0.2162	0.1099	0.021*
C7	0.83915 (12)	−0.0466 (4)	0.13777 (15)	0.0163 (9)
H7A	0.8512	−0.1400	0.1607	0.020*
H7B	0.8099	−0.0395	0.1284	0.020*
C8	0.84714 (12)	0.2525 (4)	0.13602 (16)	0.0154 (9)
C9	0.87097 (11)	0.3202 (4)	0.10800 (16)	0.0151 (9)
C10	0.91286 (12)	0.3682 (4)	0.13121 (17)	0.0194 (9)
H10	0.9318	0.3559	0.1711	0.023*
C11	0.92606 (12)	0.4327 (4)	0.09561 (17)	0.0211 (10)
H11	0.9539	0.4651	0.1116	0.025*
C12	0.89836 (13)	0.4514 (4)	0.03508 (18)	0.0246 (10)
H12	0.9081	0.4924	0.0111	0.029*
C13	0.85601 (12)	0.4080 (4)	0.01113 (17)	0.0177 (9)
H13	0.8370	0.4218	−0.0286	0.021*
C14	0.84364 (12)	0.3449 (4)	0.04796 (16)	0.0163 (9)
C15	0.80162 (12)	0.2343 (4)	0.08046 (16)	0.0192 (9)
C16	0.82163 (14)	0.5041 (4)	0.15488 (17)	0.0275 (11)
H16A	0.7928	0.4790	0.1275	0.041*
H16B	0.8336	0.5608	0.1350	0.041*
H16C	0.8228	0.5664	0.1861	0.041*
C17	0.84726 (12)	−0.0104 (4)	0.25245 (15)	0.0145 (9)
C18	0.80632 (12)	−0.0352 (5)	0.24449 (16)	0.0223 (10)
H18	0.7851	0.0364	0.2230	0.027*
C19	0.79734 (13)	−0.1614 (5)	0.26757 (17)	0.0234 (10)
H19	0.7700	−0.1745	0.2607	0.028*
C20	0.82776 (13)	−0.2718 (4)	0.30111 (16)	0.0203 (10)
C21	0.86876 (13)	−0.2481 (4)	0.31048 (17)	0.0233 (10)
H21	0.8900	−0.3187	0.3329	0.028*
C22	0.87787 (13)	−0.1194 (5)	0.28639 (17)	0.0247 (10)
H22	0.9052	−0.1060	0.2932	0.030*
C23	0.86044 (12)	−0.5343 (5)	0.37319 (17)	0.0286 (11)
H23A	0.8693	−0.5819	0.3479	0.043*
H23B	0.8557	−0.6130	0.3952	0.043*
H23C	0.8820	−0.4646	0.3997	0.043*
C24	0.95764 (12)	0.0014 (4)	0.15326 (17)	0.0207 (10)
H24	0.9759	0.0637	0.1846	0.025*
C25	0.97545 (12)	−0.0613 (4)	0.11979 (16)	0.0165 (9)
C26	1.00906 (12)	0.0163 (4)	0.11886 (17)	0.0233 (10)
H26	1.0188	0.1081	0.1400	0.028*
C27	1.02810 (12)	−0.0368 (5)	0.08835 (18)	0.0254 (10)
H27	1.0496	0.0210	0.0883	0.031*
C28	1.01570 (12)	−0.1768 (4)	0.05726 (17)	0.0226 (10)
C29	0.98184 (13)	−0.2554 (4)	0.05714 (18)	0.0249 (10)
H29	0.9723	−0.3472	0.0359	0.030*
C30	0.96232 (13)	−0.2024 (4)	0.08701 (18)	0.0232 (10)
H30	0.9402	−0.2590	0.0859	0.028*
C31	1.07740 (13)	−0.1205 (4)	0.02636 (19)	0.0291 (11)
H31A	1.0637	−0.0238	0.0093	0.044*
H31B	1.0918	−0.1576	0.0064	0.044*
H31C	1.0974	−0.1052	0.0672	0.044*
C32	0.80877 (13)	−0.1550 (4)	0.03998 (16)	0.0247 (10)
H32A	0.7820	−0.1289	0.0374	0.030*
H32B	0.8154	−0.2614	0.0537	0.030*
C33	0.80392 (12)	−0.1451 (4)	−0.02036 (16)	0.0191 (9)
C34	0.78570 (11)	−0.2681 (4)	−0.05875 (17)	0.0180 (9)
H34	0.7792	−0.3589	−0.0457	0.022*
C35	0.77693 (13)	−0.2570 (5)	−0.11688 (18)	0.0288 (11)
H35	0.7646	−0.3402	−0.1423	0.035*
C36	0.78647 (13)	−0.1237 (5)	−0.13671 (18)	0.0306 (11)
H36	0.7800	−0.1160	−0.1757	0.037*
C37	0.80560 (13)	−0.0015 (5)	−0.09880 (18)	0.0288 (11)
H37	0.8126	0.0880	−0.1119	0.035*
C38	0.81437 (13)	−0.0121 (5)	−0.04127 (17)	0.0244 (10)
H38	0.8275	0.0706	−0.0159	0.029*
Cl1	0.95562 (15)	0.6560 (5)	0.26917 (14)	0.0621 (10)	0.765 (11)
C39	0.9453 (3)	0.4623 (7)	0.2825 (3)	0.050 (2)	0.765 (11)
H39A	0.9163	0.4362	0.2546	0.060*	0.765 (11)
H39B	0.9634	0.3917	0.2762	0.060*	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)
H39C	0.9115	0.5868	0.2750	0.058*	0.235 (11)
H39D	0.9188	0.4246	0.2543	0.058*	0.235 (11)
Cl2	0.95372 (4)	0.43615 (14)	0.35449 (6)	0.0482 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0261 (7)	0.0307 (6)	0.0351 (7)	−0.0029 (6)	0.0166 (6)	0.0082 (6)
S2	0.0301 (7)	0.0283 (6)	0.0334 (7)	0.0046 (5)	0.0213 (6)	0.0022 (6)
O1	0.0125 (15)	0.0322 (16)	0.0118 (15)	0.0005 (13)	−0.0006 (13)	−0.0042 (13)
O2	0.0099 (15)	0.0301 (15)	0.0189 (16)	−0.0067 (13)	0.0049 (13)	0.0066 (13)
N1	0.0142 (18)	0.0185 (16)	0.0123 (18)	−0.0033 (15)	0.0027 (15)	−0.0038 (15)
N2	0.0154 (18)	0.0216 (17)	0.0151 (18)	−0.0049 (15)	0.0104 (15)	0.0053 (15)
N3	0.0218 (19)	0.0154 (16)	0.0154 (18)	0.0015 (15)	0.0122 (16)	0.0002 (15)
C1	0.028 (3)	0.018 (2)	0.017 (2)	0.0012 (19)	0.013 (2)	−0.0018 (18)
C2	0.015 (2)	0.024 (2)	0.015 (2)	−0.0008 (19)	0.0060 (19)	−0.0012 (19)
C3	0.014 (2)	0.0155 (19)	0.009 (2)	0.0007 (18)	0.0065 (17)	0.0044 (17)
C4	0.018 (2)	0.0125 (19)	0.015 (2)	0.0009 (18)	0.007 (2)	0.0051 (18)
C5	0.012 (2)	0.022 (2)	0.013 (2)	−0.0010 (18)	0.0078 (18)	0.0014 (18)
C6	0.021 (2)	0.017 (2)	0.019 (2)	−0.0050 (19)	0.012 (2)	−0.0017 (18)
C7	0.017 (2)	0.025 (2)	0.010 (2)	0.0001 (19)	0.0094 (18)	0.0006 (18)
C8	0.013 (2)	0.022 (2)	0.011 (2)	0.0007 (19)	0.0057 (18)	−0.0002 (18)
C9	0.013 (2)	0.0135 (19)	0.017 (2)	0.0002 (18)	0.0057 (19)	0.0039 (18)
C10	0.016 (2)	0.013 (2)	0.019 (2)	0.0025 (18)	0.0008 (19)	0.0029 (18)
C11	0.013 (2)	0.019 (2)	0.030 (3)	−0.0009 (19)	0.009 (2)	0.002 (2)
C12	0.029 (3)	0.019 (2)	0.029 (3)	0.003 (2)	0.017 (2)	0.002 (2)
C13	0.018 (2)	0.021 (2)	0.015 (2)	0.0021 (19)	0.0090 (19)	0.0025 (18)
C14	0.015 (2)	0.016 (2)	0.013 (2)	0.0060 (18)	0.0032 (18)	−0.0002 (18)
C15	0.014 (2)	0.026 (2)	0.011 (2)	0.004 (2)	0.0020 (18)	0.0010 (19)
C16	0.041 (3)	0.028 (2)	0.022 (3)	0.008 (2)	0.022 (2)	0.006 (2)
C17	0.016 (2)	0.0167 (19)	0.008 (2)	−0.0033 (18)	0.0042 (18)	−0.0037 (17)
C18	0.019 (2)	0.032 (2)	0.011 (2)	0.002 (2)	0.0042 (19)	−0.001 (2)
C19	0.017 (2)	0.029 (2)	0.023 (3)	−0.001 (2)	0.010 (2)	−0.008 (2)
C20	0.025 (2)	0.029 (2)	0.011 (2)	−0.007 (2)	0.0120 (19)	−0.0068 (19)
C21	0.018 (2)	0.026 (2)	0.024 (2)	0.004 (2)	0.009 (2)	0.006 (2)
C22	0.016 (2)	0.038 (3)	0.017 (2)	−0.006 (2)	0.006 (2)	−0.003 (2)
C23	0.031 (3)	0.036 (3)	0.024 (3)	−0.007 (2)	0.018 (2)	0.003 (2)
C24	0.017 (2)	0.017 (2)	0.017 (2)	−0.0038 (19)	−0.0003 (19)	0.0012 (19)
C25	0.015 (2)	0.018 (2)	0.016 (2)	0.0048 (18)	0.0077 (19)	0.0028 (18)
C26	0.018 (2)	0.024 (2)	0.023 (2)	−0.001 (2)	0.006 (2)	−0.004 (2)
C27	0.014 (2)	0.029 (2)	0.029 (3)	−0.002 (2)	0.007 (2)	−0.002 (2)
C28	0.019 (2)	0.023 (2)	0.022 (2)	0.002 (2)	0.008 (2)	0.007 (2)
C29	0.024 (3)	0.022 (2)	0.027 (3)	0.000 (2)	0.011 (2)	−0.001 (2)
C30	0.019 (2)	0.017 (2)	0.033 (3)	−0.0006 (19)	0.013 (2)	0.002 (2)
C31	0.038 (3)	0.027 (2)	0.042 (3)	0.007 (2)	0.035 (3)	0.005 (2)
C32	0.020 (2)	0.029 (2)	0.019 (2)	−0.011 (2)	0.004 (2)	−0.004 (2)
C33	0.014 (2)	0.030 (2)	0.012 (2)	−0.001 (2)	0.0049 (19)	0.000 (2)
C34	0.014 (2)	0.017 (2)	0.024 (2)	−0.0007 (18)	0.0102 (19)	−0.0014 (19)
C35	0.025 (3)	0.037 (3)	0.020 (2)	0.000 (2)	0.008 (2)	−0.011 (2)
C36	0.034 (3)	0.033 (3)	0.019 (3)	−0.001 (2)	0.009 (2)	−0.002 (2)
C37	0.030 (3)	0.034 (2)	0.025 (3)	−0.002 (2)	0.015 (2)	0.005 (2)
C38	0.027 (2)	0.028 (2)	0.014 (2)	−0.009 (2)	0.006 (2)	−0.009 (2)
Cl1	0.062 (2)	0.0615 (18)	0.0748 (16)	−0.0259 (16)	0.0424 (15)	−0.0276 (14)
C39	0.034 (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)
Cl2	0.0323 (7)	0.0441 (7)	0.0626 (9)	0.0007 (6)	0.0191 (7)	−0.0107 (7)

Geometric parameters (Å, º) top

S1—C20	1.760 (4)	C18—H18	0.9300
S1—C23	1.797 (4)	C19—C20	1.394 (5)
S2—C28	1.742 (4)	C19—H19	0.9300
S2—C31	1.799 (4)	C20—C21	1.405 (5)
O1—C4	1.233 (4)	C21—C22	1.394 (5)
O2—C15	1.220 (4)	C21—H21	0.9300
N1—C6	1.467 (4)	C22—H22	0.9300
N1—C7	1.467 (4)	C23—H23A	0.9600
N1—C32	1.474 (4)	C23—H23B	0.9600
N2—C15	1.378 (4)	C23—H23C	0.9600
N2—C14	1.409 (4)	C24—C25	1.429 (5)
N3—C16	1.459 (4)	C24—H24	0.9300
N3—C1	1.464 (4)	C25—C26	1.406 (5)
N3—C8	1.493 (4)	C25—C30	1.428 (5)
C1—C2	1.518 (5)	C26—C27	1.370 (5)
C1—H1A	0.9700	C26—H26	0.9300
C1—H1B	0.9700	C27—C28	1.399 (5)
C2—C17	1.495 (5)	C27—H27	0.9300
C2—C3	1.576 (5)	C28—C29	1.406 (5)
C2—H2	0.9800	C29—C30	1.370 (5)
C3—C4	1.528 (5)	C29—H29	0.9300
C3—C7	1.539 (5)	C30—H30	0.9300
C3—C8	1.588 (5)	C31—H31A	0.9600
C4—C5	1.482 (5)	C31—H31B	0.9600
C5—C24	1.373 (5)	C31—H31C	0.9600
C5—C6	1.511 (5)	C32—C33	1.503 (5)
C6—H6A	0.9700	C32—H32A	0.9700
C6—H6B	0.9700	C32—H32B	0.9700
C7—H7A	0.9700	C33—C34	1.384 (5)
C7—H7B	0.9700	C33—C38	1.402 (5)
C8—C9	1.504 (5)	C34—C35	1.395 (5)
C8—C15	1.585 (5)	C34—H34	0.9300
C9—C10	1.399 (5)	C35—C36	1.374 (5)
C9—C14	1.401 (5)	C35—H35	0.9300
C10—C11	1.361 (5)	C36—C37	1.377 (5)
C10—H10	0.9300	C36—H36	0.9300
C11—C12	1.406 (5)	C37—C38	1.380 (5)
C11—H11	0.9300	C37—H37	0.9300
C12—C13	1.400 (5)	C38—H38	0.9300
C12—H12	0.9300	Cl1—C39	1.783 (6)
C13—C14	1.363 (5)	C39—Cl2	1.767 (6)
C13—H13	0.9300	C39—H39A	0.9700
C16—H16A	0.9600	C39—H39B	0.9700
C16—H16B	0.9600	Cl1'—C39'	1.778 (10)
C16—H16C	0.9600	C39'—Cl2	1.770 (10)
C17—C22	1.392 (5)	C39'—H39C	0.9700
C17—C18	1.418 (5)	C39'—H39D	0.9700
C18—C19	1.360 (5)

C20—S1—C23	104.20 (19)	C17—C18—H18	119.3
C28—S2—C31	103.65 (18)	C18—C19—C20	122.3 (4)
C6—N1—C7	108.5 (3)	C18—C19—H19	118.9
C6—N1—C32	110.6 (3)	C20—C19—H19	118.9
C7—N1—C32	110.7 (3)	C19—C20—C21	117.2 (4)
C15—N2—C14	110.8 (3)	C19—C20—S1	118.0 (3)
C16—N3—C1	114.2 (3)	C21—C20—S1	124.8 (3)
C16—N3—C8	115.9 (3)	C22—C21—C20	120.5 (4)
C1—N3—C8	105.3 (3)	C22—C21—H21	119.8
N3—C1—C2	102.3 (3)	C20—C21—H21	119.8
N3—C1—H1A	111.3	C17—C22—C21	122.0 (4)
C2—C1—H1A	111.3	C17—C22—H22	119.0
N3—C1—H1B	111.3	C21—C22—H22	119.0
C2—C1—H1B	111.3	S1—C23—H23A	109.5
H1A—C1—H1B	109.2	S1—C23—H23B	109.5
C17—C2—C1	116.8 (3)	H23A—C23—H23B	109.5
C17—C2—C3	115.9 (3)	S1—C23—H23C	109.5
C1—C2—C3	103.1 (3)	H23A—C23—H23C	109.5
C17—C2—H2	106.8	H23B—C23—H23C	109.5
C1—C2—H2	106.8	C5—C24—C25	131.1 (4)
C3—C2—H2	106.8	C5—C24—H24	114.4
C4—C3—C7	106.2 (3)	C25—C24—H24	114.4
C4—C3—C2	111.0 (3)	C26—C25—C30	115.5 (3)
C7—C3—C2	113.3 (3)	C26—C25—C24	119.6 (3)
C4—C3—C8	109.8 (3)	C30—C25—C24	124.9 (4)
C7—C3—C8	112.2 (3)	C27—C26—C25	123.2 (4)
C2—C3—C8	104.4 (3)	C27—C26—H26	118.4
O1—C4—C5	121.6 (3)	C25—C26—H26	118.4
O1—C4—C3	120.5 (3)	C26—C27—C28	121.1 (4)
C5—C4—C3	117.9 (3)	C26—C27—H27	119.5
C24—C5—C4	117.3 (4)	C28—C27—H27	119.5
C24—C5—C6	122.3 (3)	C27—C28—C29	116.6 (4)
C4—C5—C6	120.3 (3)	C27—C28—S2	125.6 (3)
N1—C6—C5	111.7 (3)	C29—C28—S2	117.8 (3)
N1—C6—H6A	109.3	C30—C29—C28	122.7 (4)
C5—C6—H6A	109.3	C30—C29—H29	118.6
N1—C6—H6B	109.3	C28—C29—H29	118.6
C5—C6—H6B	109.3	C29—C30—C25	120.9 (4)
H6A—C6—H6B	107.9	C29—C30—H30	119.6
N1—C7—C3	108.1 (3)	C25—C30—H30	119.6
N1—C7—H7A	110.1	S2—C31—H31A	109.5
C3—C7—H7A	110.1	S2—C31—H31B	109.5
N1—C7—H7B	110.1	H31A—C31—H31B	109.5
C3—C7—H7B	110.1	S2—C31—H31C	109.5
H7A—C7—H7B	108.4	H31A—C31—H31C	109.5
N3—C8—C9	112.0 (3)	H31B—C31—H31C	109.5
N3—C8—C15	110.0 (3)	N1—C32—C33	114.1 (3)
C9—C8—C15	100.7 (3)	N1—C32—H32A	108.7
N3—C8—C3	102.3 (3)	C33—C32—H32A	108.7
C9—C8—C3	119.1 (3)	N1—C32—H32B	108.7
C15—C8—C3	112.8 (3)	C33—C32—H32B	108.7
C10—C9—C14	117.5 (3)	H32A—C32—H32B	107.6
C10—C9—C8	132.2 (3)	C34—C33—C38	117.9 (3)
C14—C9—C8	110.1 (3)	C34—C33—C32	119.0 (3)
C11—C10—C9	120.2 (4)	C38—C33—C32	122.9 (4)
C11—C10—H10	119.9	C33—C34—C35	120.6 (4)
C9—C10—H10	119.9	C33—C34—H34	119.7
C10—C11—C12	121.3 (4)	C35—C34—H34	119.7
C10—C11—H11	119.4	C36—C35—C34	120.3 (4)
C12—C11—H11	119.4	C36—C35—H35	119.8
C13—C12—C11	119.6 (4)	C34—C35—H35	119.8
C13—C12—H12	120.2	C35—C36—C37	119.9 (4)
C11—C12—H12	120.2	C35—C36—H36	120.0
C14—C13—C12	117.8 (4)	C37—C36—H36	120.0
C14—C13—H13	121.1	C36—C37—C38	119.9 (4)
C12—C13—H13	121.1	C36—C37—H37	120.1
C13—C14—C9	123.6 (4)	C38—C37—H37	120.1
C13—C14—N2	126.4 (3)	C37—C38—C33	121.3 (4)
C9—C14—N2	110.0 (3)	C37—C38—H38	119.4
O2—C15—N2	124.4 (4)	C33—C38—H38	119.4
O2—C15—C8	127.3 (3)	Cl2—C39—Cl1	112.7 (3)
N2—C15—C8	108.2 (3)	Cl2—C39—H39A	109.0
N3—C16—H16A	109.5	Cl1—C39—H39A	109.0
N3—C16—H16B	109.5	Cl2—C39—H39B	109.0
H16A—C16—H16B	109.5	Cl1—C39—H39B	109.0
N3—C16—H16C	109.5	H39A—C39—H39B	107.8
H16A—C16—H16C	109.5	Cl2—C39'—Cl1'	110.8 (8)
H16B—C16—H16C	109.5	Cl2—C39'—H39C	109.5
C22—C17—C18	116.5 (3)	Cl1'—C39'—H39C	109.5
C22—C17—C2	119.2 (3)	Cl2—C39'—H39D	109.5
C18—C17—C2	124.3 (4)	Cl1'—C39'—H39D	109.5
C19—C18—C17	121.5 (4)	H39C—C39'—H39D	108.1
C19—C18—H18	119.3	C39—Cl2—C39'	19.7 (8)

C16—N3—C1—C2	177.5 (3)	C10—C9—C14—N2	−177.0 (3)
C8—N3—C1—C2	49.3 (3)	C8—C9—C14—N2	−0.4 (4)
N3—C1—C2—C17	−166.9 (3)	C15—N2—C14—C13	178.1 (3)
N3—C1—C2—C3	−38.6 (3)	C15—N2—C14—C9	−2.8 (4)
C17—C2—C3—C4	−97.5 (4)	C14—N2—C15—O2	−179.9 (3)
C1—C2—C3—C4	133.6 (3)	C14—N2—C15—C8	4.6 (4)
C17—C2—C3—C7	21.8 (5)	N3—C8—C15—O2	−61.5 (5)
C1—C2—C3—C7	−107.1 (3)	C9—C8—C15—O2	−179.9 (4)
C17—C2—C3—C8	144.2 (3)	C3—C8—C15—O2	52.0 (5)
C1—C2—C3—C8	15.3 (4)	N3—C8—C15—N2	113.8 (3)
C7—C3—C4—O1	−148.3 (3)	C9—C8—C15—N2	−4.5 (4)
C2—C3—C4—O1	−24.8 (5)	C3—C8—C15—N2	−132.6 (3)
C8—C3—C4—O1	90.1 (4)	C1—C2—C17—C22	−158.7 (3)
C7—C3—C4—C5	34.9 (4)	C3—C2—C17—C22	79.4 (4)
C2—C3—C4—C5	158.4 (3)	C1—C2—C17—C18	18.3 (5)
C8—C3—C4—C5	−86.7 (4)	C3—C2—C17—C18	−103.5 (4)
O1—C4—C5—C24	−16.0 (5)	C22—C17—C18—C19	−1.8 (5)
C3—C4—C5—C24	160.8 (3)	C2—C17—C18—C19	−178.9 (3)
O1—C4—C5—C6	166.1 (3)	C17—C18—C19—C20	1.2 (6)
C3—C4—C5—C6	−17.1 (5)	C18—C19—C20—C21	0.0 (6)
C7—N1—C6—C5	−52.7 (4)	C18—C19—C20—S1	178.9 (3)
C32—N1—C6—C5	−174.3 (3)	C23—S1—C20—C19	−176.4 (3)
C24—C5—C6—N1	−153.3 (3)	C23—S1—C20—C21	2.4 (4)
C4—C5—C6—N1	24.5 (5)	C19—C20—C21—C22	−0.5 (6)
C6—N1—C7—C3	76.1 (3)	S1—C20—C21—C22	−179.3 (3)
C32—N1—C7—C3	−162.3 (3)	C18—C17—C22—C21	1.2 (5)
C4—C3—C7—N1	−64.0 (4)	C2—C17—C22—C21	178.5 (3)
C2—C3—C7—N1	173.9 (3)	C20—C21—C22—C17	−0.1 (6)
C8—C3—C7—N1	56.0 (4)	C4—C5—C24—C25	−179.2 (3)
C16—N3—C8—C9	65.9 (4)	C6—C5—C24—C25	−1.4 (6)
C1—N3—C8—C9	−166.9 (3)	C5—C24—C25—C26	154.6 (4)
C16—N3—C8—C15	−45.2 (4)	C5—C24—C25—C30	−26.8 (7)
C1—N3—C8—C15	82.0 (3)	C30—C25—C26—C27	0.7 (6)
C16—N3—C8—C3	−165.3 (3)	C24—C25—C26—C27	179.4 (4)
C1—N3—C8—C3	−38.1 (3)	C25—C26—C27—C28	−2.0 (6)
C4—C3—C8—N3	−106.3 (3)	C26—C27—C28—C29	2.5 (6)
C7—C3—C8—N3	135.8 (3)	C26—C27—C28—S2	−177.4 (3)
C2—C3—C8—N3	12.8 (3)	C31—S2—C28—C27	−3.5 (4)
C4—C3—C8—C9	17.9 (4)	C31—S2—C28—C29	176.5 (3)
C7—C3—C8—C9	−100.0 (4)	C27—C28—C29—C30	−1.9 (6)
C2—C3—C8—C9	136.9 (3)	S2—C28—C29—C30	178.1 (3)
C4—C3—C8—C15	135.6 (3)	C28—C29—C30—C25	0.6 (6)
C7—C3—C8—C15	17.7 (4)	C26—C25—C30—C29	0.0 (6)
C2—C3—C8—C15	−105.3 (3)	C24—C25—C30—C29	−178.6 (4)
N3—C8—C9—C10	61.9 (5)	C6—N1—C32—C33	−70.4 (4)
C15—C8—C9—C10	178.8 (4)	C7—N1—C32—C33	169.3 (3)
C3—C8—C9—C10	−57.4 (5)	N1—C32—C33—C34	157.8 (3)
N3—C8—C9—C14	−114.0 (3)	N1—C32—C33—C38	−26.7 (5)
C15—C8—C9—C14	2.9 (4)	C38—C33—C34—C35	−2.0 (6)
C3—C8—C9—C14	126.7 (3)	C32—C33—C34—C35	173.7 (4)
C14—C9—C10—C11	−1.5 (5)	C33—C34—C35—C36	0.3 (6)
C8—C9—C10—C11	−177.2 (4)	C34—C35—C36—C37	1.4 (6)
C9—C10—C11—C12	−0.6 (6)	C35—C36—C37—C38	−1.3 (6)
C10—C11—C12—C13	2.3 (6)	C36—C37—C38—C33	−0.4 (6)
C11—C12—C13—C14	−1.7 (5)	C34—C33—C38—C37	2.1 (6)
C12—C13—C14—C9	−0.5 (6)	C32—C33—C38—C37	−173.4 (4)
C12—C13—C14—N2	178.4 (3)	Cl1—C39—Cl2—C39'	61 (2)
C10—C9—C14—C13	2.1 (5)	Cl1'—C39'—Cl2—C39	−58.0 (14)
C8—C9—C14—C13	178.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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

Experimental details

Crystal data
Chemical formula	C₃₈H₃₆N₃O₂S₂·CH₂Cl₂
M_r	715.74
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	113
a, b, c (Å)	36.456 (7), 8.6164 (17), 26.184 (5)
β (°)	119.58 (3)
V (Å³)	7153 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.936, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	20568, 6263, 2890
R_int	0.116
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.154, 1.01
No. of reflections	6263
No. of parameters	455
No. of restraints	40
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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

References

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

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o244

doi:10.1107/S1600536809054774

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

(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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(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