5′′-(4-Chloro­benzyl­idene)-1′-(4-chloro­phen­yl)-1′′-methyl-1′,2′,3′,5′,6′,7′,8′,8a'-octa­hydro­dispiro­[acenaphthyl­ene-1,3′-indolizine-2′,3′′-piperidine]-2,4′′(1H)-dione

Suresh, J.; Nagalakshmi, R.A.; Kumar, R.R.; Sivakumar, S.; Lakshman, P.L.N.

doi:10.1107/S160053681204545X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3315-o3316

doi:10.1107/S160053681204545X

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5′′-(4-Chlorobenzylidene)-1′-(4-chlorophenyl)-1′′-methyl-1′,2′,3′,5′,6′,7′,8′,8a'-octahydrodispiro[acenaphthylene-1,3′-indolizine-2′,3′′-piperidine]-2,4′′(1H)-dione

J. Suresh,^a R. A. Nagalakshmi,^a R. Ranjith Kumar,^b S. Sivakumar ^b and P. L. Nilantha Lakshman ^c ^*

^aDepartment of Physics, The Madura College, Madurai 625 011, India, ^bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: plakshmannilantha@ymail.com

(Received 2 November 2012; accepted 3 November 2012; online 10 November 2012)

In the title compound, C₃₇H₃₂Cl₂N₂O₂, the pyridinone ring adopts a twisted half-chair conformation. The fused pyrrolidine and piperidine rings of the octahydroindolizine unit exhibit envelope (with the C atom bound to the C atom bearing the chlorobenzene ring being the flap atom) and chair conformations, respectively. The dihedral angle between the chlorobenzene rings is 84.03 (1)°. In the crystal, C—H⋯π interactions lead to supramolecular chains along [101] that assemble in the ac plane. Connections along the b axis are of the type Cl⋯Cl [3.4065 (8) Å].

Related literature

For general properties of indolizines, see: Gundersen et al. (2007 ). For related structures, see: Sussman & Wodak (1973 ); Wodak (1975 ). For ring conformation analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₃₇H₃₂Cl₂N₂O₂
M_r = 607.55
Monoclinic, P 2₁ /n
a = 14.1346 (5) Å
b = 15.2184 (6) Å
c = 14.5603 (6) Å
β = 102.337 (1)°
V = 3059.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.21 × 0.19 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.967, T_max = 0.974
32144 measured reflections
7321 independent reflections
4492 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.113
S = 1.01
7321 reflections
389 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C52–C57 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C75—H75⋯Cg1ⁱ	0.93	2.88	3.669 (2)	144
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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 global, I. DOI: 10.1107/S160053681204545X/tk5167sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204545X/tk5167Isup2.hkl

checkCIF report

Comment top

Indolizines are electron-rich heterocycles with very low oxidation potentials. Functionalised indolizines are common substructures found in biologically important natural products and synthetic pharmaceuticals. Due to the various biological functions associated with this skeleton, it has been frequently employed as a key scaffold in the drug industry (Gundersen et al., 2007).

In the title compound (Fig.1), the pyridinone ring adopts twisted half chair conformation with atoms N2 and C3 deviating by 0.6030 (1) Å and 0.4814 (1) Å respectively from the least squares planes defined by other atoms (C2/C4/C5/C6). Within the octahydroindolizine, the six membered piperidine ring adopts a chair conformation as evident from the puckering parameters Q = 0.567 (2) Å, θ = 180 (2)° and Φ = 50 (8)° (Cremer & Pople, 1975). The dihedral angle between the two chlorobenzene rings is 84.03 (1)°, and these rings (C71—C76) and (C52—C57) form angles of 80.91 (1) and 32.50 (1)°, respectively, with the plane defined by atoms (C2/C4/C5/C6) of pyridinone ring. Each of the carbonyl bond lengths, i.e C4=O1 and C14=O2, is 1.214 (2) Å, and each of these atoms participates in two intramolecular C—H···O contacts, with the closest of these listed in Table 1. The C8—N1 bond length (1.454 (2) Å) is comparable with the Csp²—Nsp² distance found in the similar structures (Sussman & Wodak, 1973; Wodak, 1975).

A weak intermolecular C—H···π interaction, viz. C75—H75···Cg1 (Cg1 is the centroid of the ring C52—C57; symmetry code is given in Table 1) is observed. These lead to supramolecular chains along [101] that assemble in the ac plane. Connections between layers are of the type Cl···Cl (Cl1···Cl1ⁱ = 3.4065 (8) Å: symmetry code: 1 - x, 1 - y, 2 - z).

Related literature top

For general properties of indolizines, see: Gundersen et al. (2007). For related structures, see: Sussman & Wodak (1973); Wodak (1975). For ring conformation analysis, see: Cremer & Pople (1975).

Experimental top

A mixture of 1-methyl-3,5-bis[(E)-4-cholromethylidene]tetrahydro-4(1H)- pyridinone (1 mmol), acenaphthenequinone (1 mmol) and piperidine-2- carboxylic acid (1 mmol) was dissolved in isopropyl alcohol (15 ml) and heated to reflux for 60 min. After completion of the reaction, as evident from TLC, the mixture was poured into water (50 ml), the precipitated solid was filtered and washed with water (100 ml) to obtain pure yellow solid. Melting point: 518 K, Yield: 93%

Computing details top

Data collection: APEX2 (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), showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms have been omitted.

5''-(4-Chlorobenzylidene)-1'-(4-chlorophenyl)-1''-methyl- 1',2',3',5',6',7',8',8a'-octahydrodispiro[acenaphthylene-1,3'-indolizine- 2',3''-piperidine]-2,4''(1H)-dione top

Crystal data top

C₃₇H₃₂Cl₂N₂O₂	F(000) = 1272
M_r = 607.55	D_x = 1.319 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2000 reflections
a = 14.1346 (5) Å	θ = 2–31°
b = 15.2184 (6) Å	µ = 0.25 mm⁻¹
c = 14.5603 (6) Å	T = 293 K
β = 102.337 (1)°	Block, yellow
V = 3059.7 (2) Å³	0.21 × 0.19 × 0.18 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	7321 independent reflections
Radiation source: fine-focus sealed tube	4492 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 0 pixels mm^-1	θ_max = 27.9°, θ_min = 2.0°
ω and ϕ scans	h = −18→16
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −16→20
T_min = 0.967, T_max = 0.974	l = −19→17
32144 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0403P)² + 0.7517P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
7321 reflections	Δρ_max = 0.23 e Å⁻³
389 parameters	Δρ_min = −0.38 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (4)

Crystal data top

C₃₇H₃₂Cl₂N₂O₂	V = 3059.7 (2) Å³
M_r = 607.55	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.1346 (5) Å	µ = 0.25 mm⁻¹
b = 15.2184 (6) Å	T = 293 K
c = 14.5603 (6) Å	0.21 × 0.19 × 0.18 mm
β = 102.337 (1)°

Data collection top

Bruker Kappa APEXII diffractometer	7321 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4492 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.974	R_int = 0.041
32144 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.01	Δρ_max = 0.23 e Å⁻³
7321 reflections	Δρ_min = −0.38 e Å⁻³
389 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
Cl1	0.04645 (4)	0.07200 (4)	0.43166 (3)	0.07029 (19)
Cl2	0.71789 (5)	0.05345 (6)	−0.16446 (6)	0.1089 (3)
O1	0.13905 (9)	0.07134 (8)	−0.05296 (10)	0.0538 (4)
N1	−0.00938 (10)	0.28748 (10)	−0.08843 (9)	0.0402 (4)
O2	0.13090 (10)	0.42902 (8)	−0.00055 (9)	0.0547 (4)
C16	0.18467 (12)	0.32304 (11)	−0.19504 (12)	0.0380 (4)
C7	0.03322 (12)	0.19119 (11)	0.03419 (11)	0.0368 (4)
H7	0.0063	0.1416	−0.0060	0.044*
C13	0.09576 (12)	0.28443 (11)	−0.07824 (11)	0.0356 (4)
N2	0.28362 (10)	0.29147 (10)	0.05353 (10)	0.0421 (4)
C4	0.18149 (13)	0.13902 (12)	−0.02618 (11)	0.0383 (4)
C6	0.34414 (13)	0.21861 (13)	0.03624 (14)	0.0487 (5)
H6A	0.3748	0.1921	0.0958	0.058*
H6B	0.3948	0.2407	0.0068	0.058*
C71	0.04004 (12)	0.16261 (11)	0.13512 (11)	0.0371 (4)
C51	0.32365 (14)	0.09841 (12)	−0.08389 (13)	0.0473 (5)
H51	0.2793	0.0603	−0.1200	0.057*
C21	0.22039 (13)	0.31929 (13)	−0.27798 (13)	0.0463 (5)
C3	0.12964 (12)	0.21704 (11)	0.00698 (11)	0.0349 (4)
C17	0.12068 (12)	0.26047 (11)	−0.17163 (11)	0.0363 (4)
C14	0.14749 (13)	0.37636 (12)	−0.05770 (12)	0.0413 (4)
C74	0.04679 (13)	0.10710 (13)	0.31784 (12)	0.0453 (5)
C8	−0.03173 (12)	0.26980 (12)	0.00271 (12)	0.0411 (4)
H8	−0.0113	0.3195	0.0451	0.049*
C15	0.20574 (12)	0.39111 (12)	−0.12968 (12)	0.0407 (4)
C72	0.05102 (14)	0.07488 (12)	0.15926 (13)	0.0458 (5)
H72	0.0557	0.0337	0.1132	0.055*
C2	0.20079 (12)	0.26003 (12)	0.08805 (12)	0.0406 (4)
H2A	0.1698	0.3087	0.1130	0.049*
H2B	0.2216	0.2177	0.1381	0.049*
C5	0.28707 (13)	0.14998 (11)	−0.02579 (12)	0.0397 (4)
C52	0.42240 (14)	0.09202 (12)	−0.10001 (14)	0.0476 (5)
C19	0.12123 (15)	0.19024 (14)	−0.31828 (13)	0.0529 (5)
H19	0.0987	0.1454	−0.3607	0.064*
C24	0.26740 (14)	0.45710 (13)	−0.14340 (15)	0.0506 (5)
H24	0.2822	0.5033	−0.1010	0.061*
C76	0.03301 (15)	0.22134 (13)	0.20577 (12)	0.0515 (5)
H76	0.0262	0.2809	0.1915	0.062*
C20	0.18534 (15)	0.24935 (14)	−0.33970 (14)	0.0552 (5)
H20	0.2064	0.2437	−0.3957	0.066*
C23	0.30756 (14)	0.45261 (15)	−0.22372 (17)	0.0592 (6)
H23	0.3514	0.4958	−0.2325	0.071*
C12	−0.06134 (14)	0.36225 (14)	−0.13800 (14)	0.0563 (5)
H12A	−0.0443	0.3692	−0.1987	0.068*
H12B	−0.0434	0.4156	−0.1020	0.068*
C18	0.08774 (13)	0.19465 (12)	−0.23358 (12)	0.0439 (4)
H18	0.0440	0.1533	−0.2204	0.053*
C73	0.05515 (14)	0.04700 (13)	0.25014 (13)	0.0502 (5)
H73	0.0636	−0.0123	0.2653	0.060*
C75	0.03572 (15)	0.19436 (13)	0.29690 (13)	0.0531 (5)
H75	0.0301	0.2350	0.3431	0.064*
C55	0.60436 (16)	0.06903 (14)	−0.13949 (18)	0.0621 (6)
C54	0.52339 (17)	0.05391 (14)	−0.20863 (17)	0.0667 (6)
H54	0.5292	0.0367	−0.2684	0.080*
C9	−0.13872 (14)	0.25407 (15)	−0.00761 (15)	0.0601 (6)
H9A	−0.1533	0.2466	0.0541	0.072*
H9B	−0.1569	0.2005	−0.0431	0.072*
C22	0.28499 (14)	0.38774 (15)	−0.28913 (15)	0.0565 (6)
H22	0.3123	0.3884	−0.3418	0.068*
C1	0.33930 (15)	0.35679 (14)	0.11492 (15)	0.0615 (6)
H1A	0.3930	0.3756	0.0891	0.092*
H1B	0.3629	0.3317	0.1760	0.092*
H1C	0.2988	0.4063	0.1203	0.092*
C53	0.43343 (16)	0.06461 (14)	−0.18817 (16)	0.0615 (6)
H53	0.3785	0.0532	−0.2346	0.074*
C57	0.50604 (15)	0.10706 (13)	−0.03210 (14)	0.0534 (5)
H57	0.5010	0.1252	0.0277	0.064*
C10	−0.19697 (16)	0.33041 (18)	−0.05758 (16)	0.0737 (7)
H10A	−0.1842	0.3828	−0.0190	0.088*
H10B	−0.2656	0.3173	−0.0675	0.088*
C56	0.59666 (15)	0.09545 (14)	−0.05184 (16)	0.0586 (5)
H56	0.6521	0.1056	−0.0056	0.070*
C11	−0.16993 (15)	0.34676 (18)	−0.15152 (15)	0.0703 (7)
H11A	−0.2047	0.3977	−0.1814	0.084*
H11B	−0.1885	0.2965	−0.1923	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0784 (4)	0.0908 (4)	0.0412 (3)	−0.0074 (3)	0.0117 (3)	0.0230 (3)
Cl2	0.0596 (4)	0.1353 (7)	0.1435 (7)	−0.0031 (4)	0.0477 (4)	−0.0432 (6)
O1	0.0486 (8)	0.0433 (8)	0.0701 (9)	−0.0097 (7)	0.0140 (7)	−0.0120 (7)
N1	0.0354 (8)	0.0510 (9)	0.0346 (7)	0.0028 (7)	0.0082 (6)	0.0081 (7)
O2	0.0640 (9)	0.0452 (8)	0.0559 (8)	−0.0004 (7)	0.0152 (7)	−0.0112 (7)
C16	0.0324 (9)	0.0422 (10)	0.0396 (9)	0.0029 (8)	0.0079 (7)	0.0080 (8)
C7	0.0370 (9)	0.0413 (10)	0.0322 (8)	−0.0053 (8)	0.0074 (7)	−0.0008 (7)
C13	0.0367 (9)	0.0390 (10)	0.0316 (8)	−0.0041 (8)	0.0081 (7)	0.0004 (7)
N2	0.0378 (8)	0.0436 (9)	0.0435 (8)	−0.0079 (7)	0.0058 (7)	−0.0082 (7)
C4	0.0404 (10)	0.0388 (10)	0.0343 (9)	−0.0014 (9)	0.0048 (8)	0.0023 (8)
C6	0.0378 (10)	0.0545 (12)	0.0521 (11)	−0.0036 (9)	0.0061 (8)	−0.0059 (10)
C71	0.0362 (9)	0.0411 (10)	0.0346 (9)	−0.0059 (8)	0.0086 (7)	0.0028 (8)
C51	0.0434 (11)	0.0448 (11)	0.0533 (11)	−0.0020 (9)	0.0091 (9)	−0.0037 (9)
C21	0.0392 (10)	0.0571 (12)	0.0450 (10)	0.0081 (9)	0.0148 (8)	0.0119 (9)
C3	0.0358 (9)	0.0383 (9)	0.0300 (8)	−0.0033 (8)	0.0060 (7)	0.0007 (7)
C17	0.0356 (9)	0.0415 (10)	0.0316 (8)	−0.0004 (8)	0.0068 (7)	0.0029 (8)
C14	0.0420 (10)	0.0400 (10)	0.0402 (9)	0.0005 (9)	0.0052 (8)	0.0009 (8)
C74	0.0402 (10)	0.0591 (12)	0.0360 (9)	−0.0073 (9)	0.0066 (8)	0.0123 (9)
C8	0.0396 (10)	0.0507 (11)	0.0339 (9)	0.0000 (9)	0.0101 (8)	0.0047 (8)
C15	0.0363 (10)	0.0388 (10)	0.0458 (10)	−0.0006 (8)	0.0060 (8)	0.0079 (8)
C72	0.0511 (11)	0.0423 (11)	0.0446 (10)	0.0017 (9)	0.0116 (9)	0.0008 (9)
C2	0.0392 (10)	0.0473 (11)	0.0341 (9)	−0.0033 (9)	0.0051 (7)	−0.0004 (8)
C5	0.0371 (10)	0.0389 (10)	0.0419 (9)	−0.0004 (8)	0.0055 (8)	0.0015 (8)
C52	0.0468 (11)	0.0393 (10)	0.0583 (12)	0.0012 (9)	0.0149 (9)	−0.0043 (9)
C19	0.0588 (13)	0.0590 (13)	0.0412 (10)	0.0016 (11)	0.0111 (9)	−0.0087 (9)
C24	0.0432 (11)	0.0438 (11)	0.0622 (12)	−0.0055 (9)	0.0053 (10)	0.0086 (10)
C76	0.0779 (15)	0.0398 (11)	0.0392 (10)	−0.0039 (10)	0.0176 (10)	0.0036 (8)
C20	0.0577 (13)	0.0709 (14)	0.0423 (11)	0.0082 (11)	0.0229 (10)	−0.0013 (10)
C23	0.0380 (11)	0.0579 (13)	0.0840 (16)	−0.0038 (10)	0.0184 (11)	0.0239 (12)
C12	0.0519 (12)	0.0691 (14)	0.0478 (11)	0.0115 (11)	0.0100 (9)	0.0183 (10)
C18	0.0462 (11)	0.0493 (11)	0.0358 (9)	−0.0052 (9)	0.0080 (8)	−0.0011 (8)
C73	0.0538 (12)	0.0428 (11)	0.0526 (11)	0.0027 (10)	0.0079 (9)	0.0149 (9)
C75	0.0709 (14)	0.0540 (12)	0.0365 (10)	−0.0066 (11)	0.0159 (10)	−0.0019 (9)
C55	0.0493 (13)	0.0520 (13)	0.0901 (17)	0.0005 (11)	0.0260 (12)	−0.0113 (12)
C54	0.0667 (15)	0.0624 (14)	0.0772 (15)	−0.0058 (12)	0.0289 (13)	−0.0253 (12)
C9	0.0394 (11)	0.0851 (16)	0.0581 (12)	0.0032 (11)	0.0157 (9)	0.0171 (12)
C22	0.0424 (11)	0.0698 (14)	0.0638 (13)	0.0049 (11)	0.0259 (10)	0.0193 (12)
C1	0.0508 (12)	0.0633 (14)	0.0671 (13)	−0.0151 (11)	0.0050 (10)	−0.0207 (11)
C53	0.0512 (13)	0.0642 (14)	0.0698 (14)	−0.0068 (11)	0.0146 (11)	−0.0224 (11)
C57	0.0506 (12)	0.0555 (13)	0.0539 (12)	0.0084 (10)	0.0104 (10)	0.0011 (10)
C10	0.0420 (12)	0.109 (2)	0.0717 (15)	0.0186 (13)	0.0155 (11)	0.0181 (14)
C56	0.0438 (12)	0.0599 (13)	0.0708 (14)	0.0061 (10)	0.0093 (10)	−0.0020 (11)
C11	0.0470 (13)	0.0984 (18)	0.0625 (13)	0.0161 (13)	0.0048 (10)	0.0231 (13)

Geometric parameters (Å, º) top

Cl1—C74	1.7422 (17)	C72—H72	0.9300
Cl2—C55	1.736 (2)	C2—H2A	0.9700
O1—C4	1.214 (2)	C2—H2B	0.9700
N1—C8	1.454 (2)	C52—C57	1.389 (3)
N1—C12	1.459 (2)	C52—C53	1.390 (3)
N1—C13	1.462 (2)	C19—C20	1.360 (3)
O2—C14	1.214 (2)	C19—C18	1.414 (2)
C16—C15	1.395 (2)	C19—H19	0.9300
C16—C17	1.405 (2)	C24—C23	1.407 (3)
C16—C21	1.406 (2)	C24—H24	0.9300
C7—C71	1.516 (2)	C76—C75	1.382 (2)
C7—C8	1.518 (2)	C76—H76	0.9300
C7—C3	1.549 (2)	C20—H20	0.9300
C7—H7	0.9800	C23—C22	1.361 (3)
C13—C17	1.520 (2)	C23—H23	0.9300
C13—C14	1.577 (2)	C12—C11	1.524 (3)
C13—C3	1.602 (2)	C12—H12A	0.9700
N2—C2	1.450 (2)	C12—H12B	0.9700
N2—C1	1.451 (2)	C18—H18	0.9300
N2—C6	1.455 (2)	C73—H73	0.9300
C4—C5	1.500 (2)	C75—H75	0.9300
C4—C3	1.527 (2)	C55—C56	1.364 (3)
C6—C5	1.499 (2)	C55—C54	1.373 (3)
C6—H6A	0.9700	C54—C53	1.376 (3)
C6—H6B	0.9700	C54—H54	0.9300
C71—C72	1.381 (2)	C9—C10	1.517 (3)
C71—C76	1.382 (2)	C9—H9A	0.9700
C51—C5	1.336 (2)	C9—H9B	0.9700
C51—C52	1.467 (3)	C22—H22	0.9300
C51—H51	0.9300	C1—H1A	0.9600
C21—C20	1.413 (3)	C1—H1B	0.9600
C21—C22	1.417 (3)	C1—H1C	0.9600
C3—C2	1.525 (2)	C53—H53	0.9300
C17—C18	1.362 (2)	C57—C56	1.383 (3)
C14—C15	1.482 (2)	C57—H57	0.9300
C74—C75	1.364 (3)	C10—C11	1.517 (3)
C74—C73	1.368 (3)	C10—H10A	0.9700
C8—C9	1.507 (3)	C10—H10B	0.9700
C8—H8	0.9800	C56—H56	0.9300
C15—C24	1.372 (2)	C11—H11A	0.9700
C72—C73	1.379 (2)	C11—H11B	0.9700

C8—N1—C12	114.29 (14)	C57—C52—C53	117.44 (18)
C8—N1—C13	108.41 (13)	C57—C52—C51	124.71 (18)
C12—N1—C13	117.92 (14)	C53—C52—C51	117.77 (18)
C15—C16—C17	113.11 (15)	C20—C19—C18	122.18 (19)
C15—C16—C21	123.54 (16)	C20—C19—H19	118.9
C17—C16—C21	123.29 (17)	C18—C19—H19	118.9
C71—C7—C8	115.34 (14)	C15—C24—C23	117.86 (19)
C71—C7—C3	116.33 (13)	C15—C24—H24	121.1
C8—C7—C3	103.35 (13)	C23—C24—H24	121.1
C71—C7—H7	107.1	C75—C76—C71	122.07 (18)
C8—C7—H7	107.1	C75—C76—H76	119.0
C3—C7—H7	107.1	C71—C76—H76	119.0
N1—C13—C17	109.97 (13)	C19—C20—C21	120.86 (17)
N1—C13—C14	114.26 (14)	C19—C20—H20	119.6
C17—C13—C14	101.29 (13)	C21—C20—H20	119.6
N1—C13—C3	103.18 (12)	C22—C23—C24	122.75 (18)
C17—C13—C3	116.83 (13)	C22—C23—H23	118.6
C14—C13—C3	111.79 (13)	C24—C23—H23	118.6
C2—N2—C1	112.59 (14)	N1—C12—C11	109.27 (17)
C2—N2—C6	110.89 (14)	N1—C12—H12A	109.8
C1—N2—C6	111.54 (15)	C11—C12—H12A	109.8
O1—C4—C5	121.23 (16)	N1—C12—H12B	109.8
O1—C4—C3	121.60 (16)	C11—C12—H12B	109.8
C5—C4—C3	117.17 (15)	H12A—C12—H12B	108.3
N2—C6—C5	112.01 (15)	C17—C18—C19	118.81 (17)
N2—C6—H6A	109.2	C17—C18—H18	120.6
C5—C6—H6A	109.2	C19—C18—H18	120.6
N2—C6—H6B	109.2	C74—C73—C72	119.55 (17)
C5—C6—H6B	109.2	C74—C73—H73	120.2
H6A—C6—H6B	107.9	C72—C73—H73	120.2
C72—C71—C76	117.25 (16)	C74—C75—C76	118.84 (18)
C72—C71—C7	120.31 (16)	C74—C75—H75	120.6
C76—C71—C7	122.42 (16)	C76—C75—H75	120.6
C5—C51—C52	130.55 (18)	C56—C55—C54	121.0 (2)
C5—C51—H51	114.7	C56—C55—Cl2	119.89 (18)
C52—C51—H51	114.7	C54—C55—Cl2	119.13 (18)
C16—C21—C20	115.82 (17)	C55—C54—C53	119.1 (2)
C16—C21—C22	115.27 (18)	C55—C54—H54	120.5
C20—C21—C22	128.90 (18)	C53—C54—H54	120.5
C2—C3—C4	107.26 (14)	C8—C9—C10	110.89 (17)
C2—C3—C7	112.44 (13)	C8—C9—H9A	109.5
C4—C3—C7	113.04 (14)	C10—C9—H9A	109.5
C2—C3—C13	111.31 (13)	C8—C9—H9B	109.5
C4—C3—C13	109.70 (13)	C10—C9—H9B	109.5
C7—C3—C13	103.12 (13)	H9A—C9—H9B	108.0
C18—C17—C16	119.00 (16)	C23—C22—C21	120.88 (19)
C18—C17—C13	131.08 (15)	C23—C22—H22	119.6
C16—C17—C13	109.81 (14)	C21—C22—H22	119.6
O2—C14—C15	127.07 (17)	N2—C1—H1A	109.5
O2—C14—C13	124.48 (16)	N2—C1—H1B	109.5
C15—C14—C13	107.78 (14)	H1A—C1—H1B	109.5
C75—C74—C73	120.88 (16)	N2—C1—H1C	109.5
C75—C74—Cl1	119.19 (15)	H1A—C1—H1C	109.5
C73—C74—Cl1	119.90 (15)	H1B—C1—H1C	109.5
N1—C8—C9	110.34 (15)	C54—C53—C52	121.8 (2)
N1—C8—C7	100.73 (13)	C54—C53—H53	119.1
C9—C8—C7	115.74 (16)	C52—C53—H53	119.1
N1—C8—H8	109.9	C56—C57—C52	121.09 (19)
C9—C8—H8	109.9	C56—C57—H57	119.5
C7—C8—H8	109.9	C52—C57—H57	119.5
C24—C15—C16	119.59 (17)	C9—C10—C11	110.04 (18)
C24—C15—C14	132.85 (18)	C9—C10—H10A	109.7
C16—C15—C14	107.46 (15)	C11—C10—H10A	109.7
C73—C72—C71	121.41 (17)	C9—C10—H10B	109.7
C73—C72—H72	119.3	C11—C10—H10B	109.7
C71—C72—H72	119.3	H10A—C10—H10B	108.2
N2—C2—C3	108.72 (13)	C55—C56—C57	119.6 (2)
N2—C2—H2A	109.9	C55—C56—H56	120.2
C3—C2—H2A	109.9	C57—C56—H56	120.2
N2—C2—H2B	109.9	C10—C11—C12	110.47 (18)
C3—C2—H2B	109.9	C10—C11—H11A	109.6
H2A—C2—H2B	108.3	C12—C11—H11A	109.6
C51—C5—C6	124.03 (17)	C10—C11—H11B	109.6
C51—C5—C4	116.83 (16)	C12—C11—H11B	109.6
C6—C5—C4	119.11 (15)	H11A—C11—H11B	108.1

C8—N1—C13—C17	154.02 (14)	C21—C16—C15—C24	−2.6 (3)
C12—N1—C13—C17	−74.14 (19)	C17—C16—C15—C14	−3.0 (2)
C8—N1—C13—C14	−92.89 (16)	C21—C16—C15—C14	174.40 (16)
C12—N1—C13—C14	39.0 (2)	O2—C14—C15—C24	12.2 (3)
C8—N1—C13—C3	28.69 (17)	C13—C14—C15—C24	−176.95 (19)
C12—N1—C13—C3	160.53 (15)	O2—C14—C15—C16	−164.31 (18)
C2—N2—C6—C5	52.69 (19)	C13—C14—C15—C16	6.59 (18)
C1—N2—C6—C5	179.04 (16)	C76—C71—C72—C73	−0.2 (3)
C8—C7—C71—C72	146.51 (17)	C7—C71—C72—C73	−178.48 (16)
C3—C7—C71—C72	−92.2 (2)	C1—N2—C2—C3	161.35 (16)
C8—C7—C71—C76	−31.7 (2)	C6—N2—C2—C3	−72.88 (18)
C3—C7—C71—C76	89.6 (2)	C4—C3—C2—N2	61.91 (17)
C15—C16—C21—C20	−175.04 (17)	C7—C3—C2—N2	−173.22 (14)
C17—C16—C21—C20	2.1 (3)	C13—C3—C2—N2	−58.09 (18)
C15—C16—C21—C22	3.5 (3)	C52—C51—C5—C6	2.4 (3)
C17—C16—C21—C22	−179.40 (16)	C52—C51—C5—C4	−179.48 (18)
O1—C4—C3—C2	143.79 (16)	N2—C6—C5—C51	150.50 (18)
C5—C4—C3—C2	−37.17 (19)	N2—C6—C5—C4	−27.6 (2)
O1—C4—C3—C7	19.3 (2)	O1—C4—C5—C51	22.6 (2)
C5—C4—C3—C7	−161.68 (14)	C3—C4—C5—C51	−156.42 (16)
O1—C4—C3—C13	−95.18 (18)	O1—C4—C5—C6	−159.19 (17)
C5—C4—C3—C13	83.86 (17)	C3—C4—C5—C6	21.8 (2)
C71—C7—C3—C2	−33.4 (2)	C5—C51—C52—C57	31.6 (3)
C8—C7—C3—C2	94.06 (16)	C5—C51—C52—C53	−151.9 (2)
C71—C7—C3—C4	88.23 (18)	C16—C15—C24—C23	−0.4 (3)
C8—C7—C3—C4	−144.31 (14)	C14—C15—C24—C23	−176.51 (19)
C71—C7—C3—C13	−153.41 (14)	C72—C71—C76—C75	−0.7 (3)
C8—C7—C3—C13	−25.94 (16)	C7—C71—C76—C75	177.56 (18)
N1—C13—C3—C2	−121.20 (14)	C18—C19—C20—C21	−1.0 (3)
C17—C13—C3—C2	118.03 (16)	C16—C21—C20—C19	−0.1 (3)
C14—C13—C3—C2	2.04 (19)	C22—C21—C20—C19	−178.4 (2)
N1—C13—C3—C4	120.25 (14)	C15—C24—C23—C22	2.4 (3)
C17—C13—C3—C4	−0.5 (2)	C8—N1—C12—C11	−58.0 (2)
C14—C13—C3—C4	−116.51 (15)	C13—N1—C12—C11	172.85 (16)
N1—C13—C3—C7	−0.43 (16)	C16—C17—C18—C19	1.7 (3)
C17—C13—C3—C7	−121.19 (15)	C13—C17—C18—C19	177.35 (17)
C14—C13—C3—C7	122.81 (14)	C20—C19—C18—C17	0.2 (3)
C15—C16—C17—C18	174.47 (16)	C75—C74—C73—C72	−0.9 (3)
C21—C16—C17—C18	−2.9 (3)	Cl1—C74—C73—C72	177.12 (15)
C15—C16—C17—C13	−2.0 (2)	C71—C72—C73—C74	1.0 (3)
C21—C16—C17—C13	−179.45 (15)	C73—C74—C75—C76	0.0 (3)
N1—C13—C17—C18	−49.0 (2)	Cl1—C74—C75—C76	−177.98 (15)
C14—C13—C17—C18	−170.25 (18)	C71—C76—C75—C74	0.8 (3)
C3—C13—C17—C18	68.1 (2)	C56—C55—C54—C53	−0.9 (4)
N1—C13—C17—C16	126.93 (15)	Cl2—C55—C54—C53	178.73 (18)
C14—C13—C17—C16	5.71 (17)	N1—C8—C9—C10	−55.0 (2)
C3—C13—C17—C16	−115.96 (16)	C7—C8—C9—C10	−168.55 (17)
N1—C13—C14—O2	45.7 (2)	C24—C23—C22—C21	−1.5 (3)
C17—C13—C14—O2	163.85 (17)	C16—C21—C22—C23	−1.4 (3)
C3—C13—C14—O2	−71.0 (2)	C20—C21—C22—C23	176.9 (2)
N1—C13—C14—C15	−125.51 (15)	C55—C54—C53—C52	1.3 (3)
C17—C13—C14—C15	−7.35 (17)	C57—C52—C53—C54	−1.0 (3)
C3—C13—C14—C15	117.78 (15)	C51—C52—C53—C54	−177.8 (2)
C12—N1—C8—C9	57.7 (2)	C53—C52—C57—C56	0.2 (3)
C13—N1—C8—C9	−168.56 (15)	C51—C52—C57—C56	176.79 (18)
C12—N1—C8—C7	−179.52 (15)	C8—C9—C10—C11	55.3 (3)
C13—N1—C8—C7	−45.76 (17)	C54—C55—C56—C57	0.1 (3)
C71—C7—C8—N1	171.17 (14)	Cl2—C55—C56—C57	−179.47 (16)
C3—C7—C8—N1	43.08 (16)	C52—C57—C56—C55	0.2 (3)
C71—C7—C8—C9	−69.9 (2)	C9—C10—C11—C12	−56.0 (3)
C3—C7—C8—C9	162.04 (15)	N1—C12—C11—C10	56.2 (3)
C17—C16—C15—C24	179.99 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C52–C57 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.98	2.38	2.826 (2)	107
C2—H2A···O2	0.97	2.45	2.951 (2)	112
C75—H75···Cg1ⁱ	0.93	2.88	3.669 (2)	144

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

Experimental details

Crystal data
Chemical formula	C₃₇H₃₂Cl₂N₂O₂
M_r	607.55
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	14.1346 (5), 15.2184 (6), 14.5603 (6)
β (°)	102.337 (1)
V (Å³)	3059.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.21 × 0.19 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.967, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	32144, 7321, 4492
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.113, 1.01
No. of reflections	7321
No. of parameters	389
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.38

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C52–C57 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C75—H75···Cg1ⁱ	0.93	2.88	3.669 (2)	144

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

Acknowledgements

JS and RAN thank the management of Madura College for their encouragement and support. RRK thanks the DST, New Delhi, for funds under the fast-track scheme (grant No. SR/FT/CS-073/2009).

References

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
Gundersen, L.-L., Charnock, C., Negussie, A. H., Rise, F. & Teklu, S. (2007). Eur. J. Pharm. Sci. 30, 26–35. Web of Science CrossRef PubMed CAS 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
Sussman, J. L. & Wodak, S. J. (1973). Acta Cryst. B29, 2918–2926. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Wodak, S. J. (1975). Acta Cryst. B31, 569–573. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar

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Volume 68| Part 12| December 2012| Pages o3315-o3316

doi:10.1107/S160053681204545X

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

5′′-(4-Chloro­benzyl­­idene)-1′-(4-chloro­phen­yl)-1′′-methyl-1′,2′,3′,5′,6′,7′,8′,8a'-octa­hydro­di­spiro­[ace­naphthyl­ene-1,3′-indolizine-2′,3′′-piperidine]-2,4′′(1H)-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5′′-(4-Chlorobenzylidene)-1′-(4-chlorophenyl)-1′′-methyl-1′,2′,3′,5′,6′,7′,8′,8a'-octahydrodispiro[acenaphthylene-1,3′-indolizine-2′,3′′-piperidine]-2,4′′(1H)-dione