4′-(2,4-Dichloro­phen­yl)-1,1′-dimethyl­piperidine-3-spiro-3′-pyrrolidine-2′-spiro-3′′-indoline-4,2′′-dione

Nagamuthu, S.; Sribala, R.; Ranjithkumar, R.; Krishnakumar, R.V.; Srinivasan, N.

doi:10.1107/S160053681000704X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o717

doi:10.1107/S160053681000704X

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4′-(2,4-Dichlorophenyl)-1,1′-dimethylpiperidine-3-spiro-3′-pyrrolidine-2′-spiro-3′′-indoline-4,2′′-dione

S. Nagamuthu,^a R. Sribala,^a R. Ranjithkumar,^b R. V. Krishnakumar ^a and N. Srinivasan ^a ^*

^aDepartment of Physics, Thiagarajar College, Madurai 625 009, India, and ^bSchool of Chemistry, Madurai Kamaraj University, Madurai 625 021, India
^*Correspondence e-mail: vasan692000@yahoo.co.in

(Received 22 February 2010; accepted 24 February 2010; online 27 February 2010)

In the title compound, C₂₃H₂₃Cl₂N₃O₂, the pyrroline ring adopts an envelope conformation and the piperidinone ring assumes a slightly twisted chair form. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate an R₂⁸ graph-set motif and a short Cl⋯Cl contact of 3.478 (1) Å occurs.

Related literature

For the effect on halogens on the conformations of organic molecules, see: Awwadi et al. (2006 ). For the biological properties of pyrroles, see: Watson et al. (2001 ). For graph-set notation, see: Etter et al. (1990 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₃H₂₃Cl₂N₃O₂
M_r = 444.34
Triclinic, $[P \overline 1]$
a = 7.9398 (2) Å
b = 10.8747 (3) Å
c = 13.5367 (4) Å
α = 66.561 (2)°
β = 77.873 (1)°
γ = 83.203 (2)°
V = 1047.64 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 300 K
0.27 × 0.15 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.94, T_max = 0.96
27365 measured reflections
6685 independent reflections
5249 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.130
S = 1.03
6685 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1B—H1B⋯O2ⁱ	0.86	2.02	2.8547 (15)	164
Symmetry code: (i) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681000704X/ng2738sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681000704X/ng2738Isup2.hkl

checkCIF report

Comment top

Pyrrolo ring compounds are prevalent in a variety of biologically active compounds (Watson et al., 2001) and find utility in the treatment of diseases such as diabetes, cancer and viral infections. Since the biological activity depends on the conformation of rings that constitute a molecule, precise description, at atomic resolution, of the title compound is expected to supplement further studies on structure-activity relationships on these compounds. Also, the effect of halogen- subsitutions on the conformation of the molecule and consequently on the packing modes remains an area of immense interest in crystallography (Awwadi et al., 2006).

In the title compound (I), the 5-membered methyl substitued pyrroline ring adopts the envelope conformation with C5 deviating from the plane defined by the rest of the atoms of the ring by 0.639 (2) A° The puckering parameters (Cremer & Pople, 1975) of this ring are Q = 0.431 (2)Å and ϕ = 331.2 °. The piperidinone ring adopts a slightly twisted chair conformation with the N1A and C4A atoms deviating by about 0.712 (2) and -0.523 (2) A°, respectively, from the plane defined by C2A,C3,C5A and C6A with an r.m.s. deviation of 0.041 A°. The chair conformation is also evident from the corresponding puckering amplitudes [Q=0.561 (2) A°, /q = 16.0 (2)°, /f = 30.8 (6)°]. The oxindole and the dichloro substituted phenyl rings are planar.

A relatively strong intermolecular [N1B—H1B···O2(-x, -y, 1-z)] hydrogen bond relates centrrosymmetric pairs of molecules (Fig.2). These N—H···O hydrogen bonds form R⁸₂ graph set motifs (Etter et al., 1990) which are interconnected through Cl···Cl interactions [Cl1···.Cl2 (x-1, y, z) 3.478 (1) A°] leading to columns of molecules parallel to the a-axis (Fig.3). These columns resemble a 'ladder-like' arrangement of molecules much similar to the one seen in DNA, except for the twist. These columns of molecules have interactions that are van der Waals in nature.

Related literature top

For the effect on halogens on the conformations of organic molecules, see: Awwadi et al. (2006). For the biological properties of pyrroles, see: Watson et al. (2001). For graph-set notation, see: Etter et al. (1990). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of 1-methyl-3-[(E)-(2,4-dichlorophenyl)methylidene] tetrahydro-4(1H)pyridinone (1 mmol), isatin (1 mmol) and sarcosine (1 mmol) were refluxed in methanol (15 ml) for 4 h. After completion of the reaction (TLC), the mixture was poured into water (30 ml) and the precipitate was filtered off and washed with water to obtain the product as white solid (0.28 g, 85%), m.p. 190–191 °C

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. H atoms have been omitted for clarity.
	Fig. 2. A view of the molecular aggregation down the a-axis. C-bound H atoms have been omitted for clarity.

4'-(2,4-Dichlorophenyl)-1,1'-dimethylpiperidine-3-spiro-3'- pyrrolidine-2'-spiro-3''-indoline-4,2''-dione top

Crystal data top

C₂₃H₂₃Cl₂N₃O₂	Z = 2
M_r = 444.34	F(000) = 464
Triclinic, P1	D_x = 1.409 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9398 (2) Å	Cell parameters from 5536 reflections
b = 10.8747 (3) Å	θ = 5.7–61.9°
c = 13.5367 (4) Å	µ = 0.34 mm⁻¹
α = 66.561 (2)°	T = 300 K
β = 77.873 (1)°	Needle, colourless
γ = 83.203 (2)°	0.27 × 0.15 × 0.12 mm
V = 1047.64 (5) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	6685 independent reflections
Radiation source: fine-focus sealed tube	5249 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω and ϕ scan	θ_max = 31.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→11
T_min = 0.94, T_max = 0.96	k = −15→15
27365 measured reflections	l = −19→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0652P)² + 0.3075P] where P = (F_o² + 2F_c²)/3
6685 reflections	(Δ/σ)_max = 0.001
273 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₂₃H₂₃Cl₂N₃O₂	γ = 83.203 (2)°
M_r = 444.34	V = 1047.64 (5) Å³
Triclinic, P1	Z = 2
a = 7.9398 (2) Å	Mo Kα radiation
b = 10.8747 (3) Å	µ = 0.34 mm⁻¹
c = 13.5367 (4) Å	T = 300 K
α = 66.561 (2)°	0.27 × 0.15 × 0.12 mm
β = 77.873 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	6685 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5249 reflections with I > 2σ(I)
T_min = 0.94, T_max = 0.96	R_int = 0.025
27365 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.03	Δρ_max = 0.47 e Å⁻³
6685 reflections	Δρ_min = −0.47 e Å⁻³
273 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Cl1	−0.05606 (6)	0.11850 (5)	−0.16644 (3)	0.05328 (12)
Cl2	0.52639 (5)	0.22216 (6)	−0.08290 (4)	0.05850 (14)
O1	0.59398 (16)	0.37748 (14)	0.13813 (10)	0.0564 (3)
O2	0.01383 (13)	0.08370 (10)	0.35005 (9)	0.0392 (2)
N1	0.07639 (15)	0.36986 (11)	0.21024 (10)	0.0342 (2)
N1A	0.40225 (16)	0.01730 (11)	0.32854 (10)	0.0369 (2)
N1B	0.09730 (16)	0.15644 (12)	0.46891 (9)	0.0372 (3)
H1B	0.0533	0.0947	0.5293	0.045*
C1A	0.3736 (3)	−0.12482 (15)	0.36383 (15)	0.0521 (4)
H7	0.4034	−0.1725	0.4350	0.078*
H8	0.4440	−0.1588	0.3127	0.078*
H9	0.2544	−0.1368	0.3671	0.078*
C2	0.19382 (16)	0.28182 (11)	0.28156 (10)	0.0277 (2)
C2A	0.35737 (18)	0.09368 (13)	0.22132 (11)	0.0330 (3)
H1	0.2483	0.0647	0.2182	0.040*
H2	0.4449	0.0771	0.1657	0.040*
C2B	0.09267 (16)	0.15968 (12)	0.36880 (10)	0.0312 (2)
C3	0.34300 (15)	0.24405 (12)	0.19834 (10)	0.0275 (2)
C4	0.29884 (17)	0.33178 (13)	0.08305 (10)	0.0317 (2)
H4	0.4047	0.3711	0.0334	0.038*
C4A	0.51969 (17)	0.28084 (14)	0.20663 (11)	0.0354 (3)
C4B	0.24667 (17)	0.34208 (13)	0.35377 (11)	0.0321 (2)
C5	0.1825 (2)	0.44231 (13)	0.10524 (11)	0.0383 (3)
H5A	0.2488	0.5087	0.1098	0.046*
H5B	0.1127	0.4863	0.0489	0.046*
C5A	0.5987 (2)	0.18768 (17)	0.30320 (14)	0.0442 (3)
H51	0.5450	0.2069	0.3671	0.053*
H52	0.7204	0.2048	0.2887	0.053*
C5B	0.18216 (18)	0.26551 (14)	0.46247 (11)	0.0347 (3)
C6A	0.5790 (2)	0.04095 (17)	0.32825 (14)	0.0475 (4)
H61	0.6566	0.0149	0.2736	0.057*
H62	0.6093	−0.0134	0.3992	0.057*
C6B	0.3263 (2)	0.45973 (15)	0.32860 (14)	0.0451 (3)
H6B	0.3695	0.5129	0.2563	0.054*
C7B	0.3409 (3)	0.49719 (19)	0.41348 (18)	0.0583 (5)
H7B	0.3940	0.5763	0.3976	0.070*
C8B	0.2777 (3)	0.4188 (2)	0.52044 (17)	0.0591 (5)
H8B	0.2893	0.4457	0.5758	0.071*
C9B	0.1972 (2)	0.30098 (19)	0.54744 (14)	0.0496 (4)
H9B	0.1550	0.2477	0.6198	0.060*
C11	−0.0503 (2)	0.45116 (18)	0.25448 (16)	0.0506 (4)
H11A	−0.1084	0.3957	0.3257	0.076*
H11B	−0.1328	0.4910	0.2068	0.076*
H11C	0.0066	0.5205	0.2603	0.076*
C41	0.21203 (16)	0.26281 (13)	0.03025 (10)	0.0303 (2)
C42	0.03314 (17)	0.25080 (14)	0.05212 (11)	0.0338 (3)
H42	−0.0324	0.2744	0.1079	0.041*
C43	−0.04964 (18)	0.20518 (15)	−0.00610 (12)	0.0375 (3)
H43	−0.1689	0.1990	0.0101	0.045*
C44	0.04591 (19)	0.16899 (14)	−0.08833 (11)	0.0362 (3)
C45	0.22301 (19)	0.17398 (16)	−0.11040 (12)	0.0407 (3)
H45	0.2879	0.1472	−0.1646	0.049*
C46	0.30248 (17)	0.21960 (15)	−0.05036 (11)	0.0360 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0568 (2)	0.0684 (3)	0.0460 (2)	−0.01210 (19)	−0.01697 (18)	−0.02727 (19)
Cl2	0.02974 (17)	0.0955 (4)	0.0552 (2)	−0.00686 (19)	0.00060 (15)	−0.0370 (2)
O1	0.0472 (6)	0.0649 (8)	0.0476 (6)	−0.0279 (6)	−0.0104 (5)	−0.0039 (6)
O2	0.0388 (5)	0.0369 (5)	0.0401 (5)	−0.0137 (4)	−0.0071 (4)	−0.0095 (4)
N1	0.0374 (6)	0.0304 (5)	0.0346 (5)	0.0055 (4)	−0.0123 (4)	−0.0115 (4)
N1A	0.0425 (6)	0.0310 (5)	0.0334 (6)	0.0047 (4)	−0.0116 (5)	−0.0077 (4)
N1B	0.0422 (6)	0.0363 (6)	0.0279 (5)	−0.0105 (5)	0.0006 (4)	−0.0080 (4)
C1A	0.0657 (11)	0.0321 (7)	0.0479 (9)	0.0045 (7)	−0.0105 (8)	−0.0058 (6)
C2	0.0312 (5)	0.0245 (5)	0.0260 (5)	−0.0040 (4)	−0.0068 (4)	−0.0068 (4)
C2A	0.0387 (6)	0.0298 (6)	0.0299 (6)	0.0005 (5)	−0.0078 (5)	−0.0107 (5)
C2B	0.0296 (5)	0.0298 (6)	0.0311 (6)	−0.0048 (4)	−0.0041 (4)	−0.0080 (5)
C3	0.0289 (5)	0.0270 (5)	0.0247 (5)	−0.0039 (4)	−0.0063 (4)	−0.0064 (4)
C4	0.0345 (6)	0.0319 (6)	0.0251 (5)	−0.0082 (5)	−0.0074 (4)	−0.0044 (4)
C4A	0.0309 (6)	0.0414 (7)	0.0347 (6)	−0.0059 (5)	−0.0068 (5)	−0.0137 (5)
C4B	0.0360 (6)	0.0301 (6)	0.0318 (6)	−0.0034 (5)	−0.0085 (5)	−0.0118 (5)
C5	0.0516 (8)	0.0264 (6)	0.0342 (6)	−0.0011 (5)	−0.0176 (6)	−0.0042 (5)
C5A	0.0366 (7)	0.0537 (9)	0.0452 (8)	0.0010 (6)	−0.0187 (6)	−0.0171 (7)
C5B	0.0356 (6)	0.0377 (6)	0.0318 (6)	−0.0004 (5)	−0.0058 (5)	−0.0148 (5)
C6A	0.0436 (8)	0.0490 (8)	0.0475 (8)	0.0132 (7)	−0.0194 (7)	−0.0145 (7)
C6B	0.0556 (9)	0.0349 (7)	0.0478 (8)	−0.0114 (6)	−0.0114 (7)	−0.0154 (6)
C7B	0.0708 (12)	0.0480 (9)	0.0728 (12)	−0.0092 (8)	−0.0219 (10)	−0.0343 (9)
C8B	0.0691 (12)	0.0685 (12)	0.0616 (11)	−0.0013 (9)	−0.0188 (9)	−0.0448 (10)
C9B	0.0564 (9)	0.0613 (10)	0.0385 (8)	−0.0003 (8)	−0.0084 (7)	−0.0275 (7)
C11	0.0498 (9)	0.0479 (9)	0.0586 (10)	0.0166 (7)	−0.0174 (7)	−0.0263 (8)
C41	0.0312 (6)	0.0328 (6)	0.0238 (5)	−0.0038 (4)	−0.0070 (4)	−0.0059 (4)
C42	0.0313 (6)	0.0396 (7)	0.0306 (6)	−0.0019 (5)	−0.0057 (5)	−0.0132 (5)
C43	0.0304 (6)	0.0449 (7)	0.0379 (7)	−0.0035 (5)	−0.0085 (5)	−0.0149 (6)
C44	0.0400 (7)	0.0389 (7)	0.0312 (6)	−0.0039 (5)	−0.0127 (5)	−0.0111 (5)
C45	0.0405 (7)	0.0514 (8)	0.0329 (7)	−0.0016 (6)	−0.0050 (5)	−0.0198 (6)
C46	0.0284 (6)	0.0461 (7)	0.0313 (6)	−0.0028 (5)	−0.0036 (5)	−0.0129 (5)

Geometric parameters (Å, º) top

Cl1—C44	1.7326 (14)	C4B—C5B	1.3894 (19)
Cl2—C46	1.7402 (14)	C5—H5A	0.9700
O1—C4A	1.2057 (18)	C5—H5B	0.9700
O2—C2B	1.2226 (16)	C5A—C6A	1.514 (2)
N1—C11	1.4524 (19)	C5A—H51	0.9700
N1—C5	1.4539 (19)	C5A—H52	0.9700
N1—C2	1.4661 (16)	C5B—C9B	1.381 (2)
N1A—C2A	1.4531 (17)	C6A—H61	0.9700
N1A—C6A	1.455 (2)	C6A—H62	0.9700
N1A—C1A	1.456 (2)	C6B—C7B	1.392 (2)
N1B—C2B	1.3498 (17)	C6B—H6B	0.9300
N1B—C5B	1.3966 (18)	C7B—C8B	1.374 (3)
N1B—H1B	0.8600	C7B—H7B	0.9300
C1A—H7	0.9600	C8B—C9B	1.381 (3)
C1A—H8	0.9600	C8B—H8B	0.9300
C1A—H9	0.9600	C9B—H9B	0.9300
C2—C4B	1.5192 (17)	C11—H11A	0.9600
C2—C2B	1.5524 (16)	C11—H11B	0.9600
C2—C3	1.5916 (17)	C11—H11C	0.9600
C2A—C3	1.5329 (17)	C41—C46	1.3879 (19)
C2A—H1	0.9700	C41—C42	1.3995 (17)
C2A—H2	0.9700	C42—C43	1.3801 (19)
C3—C4A	1.5413 (17)	C42—H42	0.9300
C3—C4	1.5604 (17)	C43—C44	1.376 (2)
C4—C5	1.515 (2)	C43—H43	0.9300
C4—C41	1.5180 (17)	C44—C45	1.378 (2)
C4—H4	0.9800	C45—C46	1.384 (2)
C4A—C5A	1.507 (2)	C45—H45	0.9300
C4B—C6B	1.3811 (19)

C11—N1—C5	115.62 (12)	H5A—C5—H5B	109.2
C11—N1—C2	117.09 (12)	C4A—C5A—C6A	113.15 (13)
C5—N1—C2	106.73 (11)	C4A—C5A—H51	108.9
C2A—N1A—C6A	110.22 (12)	C6A—C5A—H51	108.9
C2A—N1A—C1A	111.33 (12)	C4A—C5A—H52	108.9
C6A—N1A—C1A	111.91 (13)	C6A—C5A—H52	108.9
C2B—N1B—C5B	111.76 (11)	H51—C5A—H52	107.8
C2B—N1B—H1B	124.1	C9B—C5B—C4B	122.56 (14)
C5B—N1B—H1B	124.2	C9B—C5B—N1B	127.53 (14)
N1A—C1A—H7	109.5	C4B—C5B—N1B	109.84 (12)
N1A—C1A—H8	109.5	N1A—C6A—C5A	110.31 (12)
H7—C1A—H8	109.5	N1A—C6A—H61	109.6
N1A—C1A—H9	109.5	C5A—C6A—H61	109.6
H7—C1A—H9	109.5	N1A—C6A—H62	109.6
H8—C1A—H9	109.5	C5A—C6A—H62	109.6
N1—C2—C4B	113.50 (10)	H61—C6A—H62	108.1
N1—C2—C2B	108.33 (10)	C4B—C6B—C7B	118.74 (16)
C4B—C2—C2B	101.02 (10)	C4B—C6B—H6B	120.6
N1—C2—C3	102.91 (9)	C7B—C6B—H6B	120.6
C4B—C2—C3	117.36 (10)	C8B—C7B—C6B	120.87 (16)
C2B—C2—C3	113.80 (10)	C8B—C7B—H7B	119.6
N1A—C2A—C3	110.54 (10)	C6B—C7B—H7B	119.6
N1A—C2A—H1	109.5	C7B—C8B—C9B	121.36 (15)
C3—C2A—H1	109.5	C7B—C8B—H8B	119.3
N1A—C2A—H2	109.5	C9B—C8B—H8B	119.3
C3—C2A—H2	109.5	C8B—C9B—C5B	117.24 (16)
H1—C2A—H2	108.1	C8B—C9B—H9B	121.4
O2—C2B—N1B	125.61 (12)	C5B—C9B—H9B	121.4
O2—C2B—C2	125.83 (12)	N1—C11—H11A	109.5
N1B—C2B—C2	108.44 (10)	N1—C11—H11B	109.5
C2A—C3—C4A	106.08 (10)	H11A—C11—H11B	109.5
C2A—C3—C4	112.94 (10)	N1—C11—H11C	109.5
C4A—C3—C4	109.87 (10)	H11A—C11—H11C	109.5
C2A—C3—C2	113.02 (10)	H11B—C11—H11C	109.5
C4A—C3—C2	110.45 (10)	C46—C41—C42	115.70 (12)
C4—C3—C2	104.55 (10)	C46—C41—C4	122.16 (12)
C5—C4—C41	111.19 (11)	C42—C41—C4	121.86 (12)
C5—C4—C3	102.12 (10)	C43—C42—C41	122.42 (13)
C41—C4—C3	116.79 (10)	C43—C42—H42	118.8
C5—C4—H4	108.8	C41—C42—H42	118.8
C41—C4—H4	108.8	C44—C43—C42	119.36 (13)
C3—C4—H4	108.8	C44—C43—H43	120.3
O1—C4A—C5A	121.14 (13)	C42—C43—H43	120.3
O1—C4A—C3	122.06 (13)	C43—C44—C45	120.56 (13)
C5A—C4A—C3	116.78 (11)	C43—C44—Cl1	120.14 (11)
C6B—C4B—C5B	119.22 (13)	C45—C44—Cl1	119.29 (11)
C6B—C4B—C2	131.56 (13)	C44—C45—C46	118.75 (13)
C5B—C4B—C2	108.82 (11)	C44—C45—H45	120.6
N1—C5—C4	102.60 (10)	C46—C45—H45	120.6
N1—C5—H5A	111.2	C45—C46—C41	123.11 (12)
C4—C5—H5A	111.2	C45—C46—Cl2	115.88 (11)
N1—C5—H5B	111.2	C41—C46—Cl2	121.01 (11)
C4—C5—H5B	111.2

C11—N1—C2—C4B	−36.10 (17)	N1—C2—C4B—C5B	115.04 (12)
C5—N1—C2—C4B	95.27 (12)	C2B—C2—C4B—C5B	−0.69 (14)
C11—N1—C2—C2B	75.23 (15)	C3—C2—C4B—C5B	−125.00 (12)
C5—N1—C2—C2B	−153.40 (11)	C11—N1—C5—C4	179.57 (12)
C11—N1—C2—C3	−163.97 (12)	C2—N1—C5—C4	47.39 (13)
C5—N1—C2—C3	−32.60 (12)	C41—C4—C5—N1	84.59 (12)
C6A—N1A—C2A—C3	−69.88 (14)	C3—C4—C5—N1	−40.70 (12)
C1A—N1A—C2A—C3	165.32 (13)	O1—C4A—C5A—C6A	−136.43 (17)
C5B—N1B—C2B—O2	−173.19 (13)	C3—C4A—C5A—C6A	41.83 (19)
C5B—N1B—C2B—C2	3.01 (16)	C6B—C4B—C5B—C9B	−1.3 (2)
N1—C2—C2B—O2	55.31 (17)	C2—C4B—C5B—C9B	−174.82 (14)
C4B—C2—C2B—O2	174.82 (13)	C6B—C4B—C5B—N1B	176.05 (14)
C3—C2—C2B—O2	−58.48 (17)	C2—C4B—C5B—N1B	2.48 (16)
N1—C2—C2B—N1B	−120.88 (12)	C2B—N1B—C5B—C9B	173.59 (15)
C4B—C2—C2B—N1B	−1.37 (13)	C2B—N1B—C5B—C4B	−3.54 (17)
C3—C2—C2B—N1B	125.33 (11)	C2A—N1A—C6A—C5A	61.70 (16)
N1A—C2A—C3—C4A	58.36 (13)	C1A—N1A—C6A—C5A	−173.83 (14)
N1A—C2A—C3—C4	178.76 (10)	C4A—C5A—C6A—N1A	−47.18 (19)
N1A—C2A—C3—C2	−62.80 (13)	C5B—C4B—C6B—C7B	0.6 (2)
N1—C2—C3—C2A	−117.16 (11)	C2—C4B—C6B—C7B	172.46 (16)
C4B—C2—C3—C2A	117.44 (11)	C4B—C6B—C7B—C8B	0.1 (3)
C2B—C2—C3—C2A	−0.17 (14)	C6B—C7B—C8B—C9B	−0.3 (3)
N1—C2—C3—C4A	124.19 (11)	C7B—C8B—C9B—C5B	−0.3 (3)
C4B—C2—C3—C4A	−1.21 (14)	C4B—C5B—C9B—C8B	1.1 (3)
C2B—C2—C3—C4A	−118.83 (11)	N1B—C5B—C9B—C8B	−175.70 (16)
N1—C2—C3—C4	6.05 (11)	C5—C4—C41—C46	142.59 (13)
C4B—C2—C3—C4	−119.35 (11)	C3—C4—C41—C46	−100.79 (14)
C2B—C2—C3—C4	123.03 (10)	C5—C4—C41—C42	−30.98 (16)
C2A—C3—C4—C5	144.01 (11)	C3—C4—C41—C42	85.64 (15)
C4A—C3—C4—C5	−97.78 (12)	C46—C41—C42—C43	−3.1 (2)
C2—C3—C4—C5	20.75 (12)	C4—C41—C42—C43	170.90 (13)
C2A—C3—C4—C41	22.49 (15)	C41—C42—C43—C44	0.5 (2)
C4A—C3—C4—C41	140.71 (12)	C42—C43—C44—C45	2.0 (2)
C2—C3—C4—C41	−100.77 (12)	C42—C43—C44—Cl1	−177.15 (11)
C2A—C3—C4A—O1	132.58 (15)	C43—C44—C45—C46	−1.8 (2)
C4—C3—C4A—O1	10.21 (19)	Cl1—C44—C45—C46	177.43 (11)
C2—C3—C4A—O1	−104.62 (16)	C44—C45—C46—C41	−1.1 (2)
C2A—C3—C4A—C5A	−45.66 (16)	C44—C45—C46—Cl2	179.75 (12)
C4—C3—C4A—C5A	−168.03 (12)	C42—C41—C46—C45	3.4 (2)
C2—C3—C4A—C5A	77.15 (15)	C4—C41—C46—C45	−170.57 (13)
N1—C2—C4B—C6B	−57.5 (2)	C42—C41—C46—Cl2	−177.48 (10)
C2B—C2—C4B—C6B	−173.18 (16)	C4—C41—C46—Cl2	8.58 (18)
C3—C2—C4B—C6B	62.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1B···O2ⁱ	0.86	2.02	2.8547 (15)	164

Symmetry code: (i) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₃Cl₂N₃O₂
M_r	444.34
Crystal system, space group	Triclinic, P1
Temperature (K)	300
a, b, c (Å)	7.9398 (2), 10.8747 (3), 13.5367 (4)
α, β, γ (°)	66.561 (2), 77.873 (1), 83.203 (2)
V (Å³)	1047.64 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.27 × 0.15 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.94, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	27365, 6685, 5249
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.726

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.130, 1.03
No. of reflections	6685
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.47

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1B···O2ⁱ	0.86	2.02	2.8547 (15)	163.9

Symmetry code: (i) −x, −y, −z+1.

Acknowledgements

The authors thank Dr Babu Varghese, Sophiticated Analytical Instrumentation Facility, Indian Institute of Technology, Chennai, for the data collection.

References

Awwadi, F. F., Willet, R. D., Peterson, K. A. & Twamley, B. (2006). Chem. Eur. J. 12, 8952–8960. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Watson, A. A., Fleet, G. W. J., Asano, N., Molyneux, R. J. & Nash, R. J. (2001). Phytochemistry, 56, 265–295. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 66| Part 3| March 2010| Page o717

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

4′-(2,4-Di­chloro­phen­yl)-1,1′-di­methyl­piperidine-3-spiro-3′-pyrrolidine-2′-spiro-3′′-indoline-4,2′′-dione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

4′-(2,4-Dichlorophenyl)-1,1′-dimethylpiperidine-3-spiro-3′-pyrrolidine-2′-spiro-3′′-indoline-4,2′′-dione