rac-Methyl (1R,3′S)-1′,1′′-dimethyl-2,2′′-dioxo-2H-dispiro­[acenaphthyl­ene-1,2′-pyrrolidine-3′,3′′-indoline]-4′-carboxyl­ate

Ganesh, G.; Yuvaraj, P.S.; Divakara, C.; Reddy, B.S.R.; SubbiahPandi, A.

doi:10.1107/S1600536813000470

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o235

doi:10.1107/S1600536813000470

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rac-Methyl (1R,3′S)-1′,1′′-dimethyl-2,2′′-dioxo-2H-dispiro[acenaphthylene-1,2′-pyrrolidine-3′,3′′-indoline]-4′-carboxylate

G. Ganesh,^a Panneer Selvam Yuvaraj,^b Chinthalapuri Divakara,^b Boreddy S. R. Reddy ^b and A. SubbiahPandi ^c ^*

^aDepartment of Physics, S.M.K. Fomra Institute of Technology, Thaiyur, Chennai 603 103, India, ^bIndustrial Chemistry Laboratory, Central Leather Research Institute, Adyar, Chennai 600 020, India, and ^cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
^*Correspondence e-mail: a_sp59@yahoo.in

(Received 22 December 2012; accepted 5 January 2013; online 12 January 2013)

In the title compound, C₂₆H₂₂N₂O₄, the pyrrolidine ring adopts a twisted conformation and the other five-membered rings adopt envelope conformations with the spiro C atoms as the flap atoms. The naphthalene ring system of the dihydroacenaphthylene group forms dihedral angles of 89.2 (9) and 75.5 (6)° with the pyrrolidine and indole rings, respectively. The pyrrolidine ring makes a dihedral angle of 80.1 (9)° with the indole ring. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming chains along the b-axis direction.

Related literature

For the biological activity of naphthalene derivatives, see: Wiltz et al. (1998 ); Wright et al. (2000 ); Varma et al. (1994 ). For a related structure, see: Wei et al. (2012 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₆H₂₂N₂O₄
M_r = 426.46
Monoclinic, P 2₁ /c
a = 15.4839 (4) Å
b = 9.5832 (2) Å
c = 15.6375 (4) Å
β = 115.184 (1)°
V = 2099.81 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.977, T_max = 0.983
19264 measured reflections
4057 independent reflections
3017 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.103
S = 1.03
4057 reflections
292 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2ⁱ	0.93	2.60	3.268 (2)	130
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813000470/lx2278sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813000470/lx2278Isup2.hkl

checkCIF report

Comment top

Naphthalene derivatives have manifested applications in many fields, for example, as a colorant, explosive, disinfectant, insecticide and plant hormone auxin. Naphthalene is believed to play a role in the chemical defence against biological enemies (Wiltz et al., 1998; Wright et al., 2000). It may be produced by metabolic processes in termites or by associated microorganisms which inhabit, e.g., the termite guts (Varma et al., 1994). In view of these importance and continuation of our work on the crystal structure analyis of napthalene derivatives, the crystal structure of the title compound has been carried out and the results are presented here.

X–Ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The geometry of acenaphthylene and pyrrolidine ring systems are comparable with the related structure [Wei et al. (2012)]. The sum of the angles at N1 [338.2 (1)°] and N2 [359.4 (1)°] of the pyrrolidine rings are in accordance with sp³ and sp² hybridizations. The naphthalene ring system of the dihydroacenaphthylene group [C7–C16] forms dihedral angles of 89.2 (8) and 75.5 (5)° with the central pyrrolidine ring [N1/C2–C5] and the indole ring [N2/C4/C17–C23], respectively. It clearly shows that the naphthalene ring system of the dihydroacenaphthylene group attached to the central pyrrolidine ring are almost perpendicular to each other. Also the dihedral angle between the central pyrrolidine and the indole ring forms a a dihedral angle of 80.1 (8)°.

The central pyrrolidine ring adopts twisted conformations on N1 and C2 atoms with the pukering parameter of q₂ = 0.3942 (2) Å, ϕ = 13.72 (3)° (Cremer & Pople, 1975). The pyrrolidine ring [N2/C4/C17–C19] in the indole group adopts envelope conformations, q₂ = 0.0889 (2) Å and ϕ = 219.39 (1)°, and with atom C17 deviating -0.0565 (2) Å from the least–squares plane passing through the remaining four atoms (N2/C19/C18/C4) of that ring. In the crystal the molecules are linked by weak intermolecular C—H···O hydrogen bonds (Table 1), forming one-dimensional chains along the b–axis.

Related literature top

For the biological activity of naphthalene derivatives, see: Wiltz et al. (1998); Wright et al. (2000); Varma et al. (1994). For a related structure, see: Wei et al. (2012). For ring conformations, see: Cremer & Pople (1975).

Experimental top

To a mixture of 1eq of (E)–methyl 2–(1–methyl–2–oxoindolin –3–ylidene) acetate, 1eq of isatin and 1.5eq of acenaphthylene–1,2 –dione were dissolved in acetonitrile. This reaction mixture refluxed at 80°C for 8 hours. The reaction mixture was monitored for completion by thin layar chromatography. Upon completion, the reaction mixture was extracted with ethyl acetate and water. The product was dried and purified by coloumn chromatography using ethyl acetate and hexane (1:9) as an elutent to affored pure Dispiro oxindole. Yield (78%). Single crystals suitable for X–ray diffraction were obtained by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.

rac-Methyl (1R,3'S)-1',1''-dimethyl-2,2''-dioxo-2H- dispiro[acenaphthylene-1,2'-pyrrolidine-3',3''-indoline]-4'-carboxylate top

Crystal data top

C₂₆H₂₂N₂O₄	F(000) = 896
M_r = 426.46	D_x = 1.349 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4057 reflections
a = 15.4839 (4) Å	θ = 1.5–25.8°
b = 9.5832 (2) Å	µ = 0.09 mm⁻¹
c = 15.6375 (4) Å	T = 293 K
β = 115.184 (1)°	Block, colourless
V = 2099.81 (9) Å³	0.25 × 0.22 × 0.19 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	4057 independent reflections
Radiation source: fine-focus sealed tube	3017 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and ϕ scans	θ_max = 25.8°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −18→18
T_min = 0.977, T_max = 0.983	k = −11→11
19264 measured reflections	l = −19→18

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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F²) = 0.103	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0432P)² + 0.5222P] where P = (F_o² + 2F_c²)/3
4057 reflections	(Δ/σ)_max < 0.001
292 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₆H₂₂N₂O₄	V = 2099.81 (9) Å³
M_r = 426.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.4839 (4) Å	µ = 0.09 mm⁻¹
b = 9.5832 (2) Å	T = 293 K
c = 15.6375 (4) Å	0.25 × 0.22 × 0.19 mm
β = 115.184 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4057 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3017 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.983	R_int = 0.031
19264 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.03	Δρ_max = 0.17 e Å⁻³
4057 reflections	Δρ_min = −0.17 e Å⁻³
292 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 > 2sigma(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
O1	0.69067 (8)	0.37535 (12)	0.28269 (9)	0.0565 (3)
O2	0.87808 (9)	0.87118 (12)	0.39458 (9)	0.0552 (3)
O3	0.64333 (11)	0.58931 (15)	0.48841 (11)	0.0762 (4)
O4	0.65285 (10)	0.81185 (13)	0.45236 (10)	0.0648 (4)
N1	0.87057 (9)	0.51097 (14)	0.41944 (9)	0.0456 (3)
N2	0.73670 (10)	0.90053 (13)	0.26438 (10)	0.0490 (3)
C1	0.91612 (13)	0.37648 (19)	0.42302 (14)	0.0590 (5)
H1A	0.8683	0.3050	0.3999	0.088*
H1B	0.9596	0.3560	0.4871	0.088*
H1C	0.9505	0.3800	0.3844	0.088*
C2	0.81537 (13)	0.51929 (18)	0.47465 (12)	0.0537 (4)
H2A	0.8562	0.5123	0.5418	0.064*
H2B	0.7673	0.4465	0.4568	0.064*
C3	0.77008 (12)	0.66228 (17)	0.44928 (11)	0.0468 (4)
H3	0.8174	0.7303	0.4890	0.056*
C4	0.75428 (11)	0.68832 (15)	0.34492 (11)	0.0385 (3)
C5	0.81077 (10)	0.56359 (15)	0.32472 (10)	0.0377 (3)
C6	0.74144 (11)	0.44844 (15)	0.25997 (12)	0.0410 (4)
C7	0.75797 (10)	0.43438 (15)	0.17441 (11)	0.0399 (4)
C8	0.71903 (12)	0.34921 (17)	0.09679 (12)	0.0503 (4)
H8	0.6677	0.2913	0.0878	0.060*
C9	0.75897 (13)	0.35191 (18)	0.03135 (12)	0.0566 (5)
H9	0.7321	0.2965	−0.0225	0.068*
C10	0.83614 (14)	0.43324 (18)	0.04395 (12)	0.0544 (4)
H10	0.8613	0.4304	−0.0004	0.065*
C11	0.87793 (12)	0.52114 (16)	0.12320 (11)	0.0437 (4)
C12	0.83529 (10)	0.52056 (15)	0.18635 (10)	0.0375 (3)
C13	0.86999 (10)	0.59774 (15)	0.27095 (11)	0.0377 (3)
C14	0.95079 (11)	0.67546 (17)	0.29344 (12)	0.0470 (4)
H14	0.9769	0.7255	0.3497	0.056*
C15	0.99391 (13)	0.67866 (19)	0.23017 (13)	0.0550 (5)
H15	1.0482	0.7331	0.2454	0.066*
C16	0.95951 (13)	0.60548 (19)	0.14783 (13)	0.0545 (4)
H16	0.9898	0.6111	0.1078	0.065*
C17	0.79970 (12)	0.82915 (16)	0.33990 (12)	0.0430 (4)
C18	0.65287 (11)	0.70826 (15)	0.27105 (11)	0.0394 (4)
C19	0.64718 (11)	0.83487 (16)	0.22577 (11)	0.0429 (4)
C20	0.56296 (13)	0.88569 (19)	0.15782 (13)	0.0555 (5)
H20	0.5609	0.9701	0.1276	0.067*
C21	0.48165 (13)	0.8071 (2)	0.13602 (14)	0.0601 (5)
H21	0.4237	0.8390	0.0902	0.072*
C22	0.48497 (12)	0.6824 (2)	0.18089 (14)	0.0584 (5)
H22	0.4292	0.6317	0.1657	0.070*
C23	0.57069 (11)	0.63162 (17)	0.24860 (12)	0.0489 (4)
H23	0.5727	0.5470	0.2785	0.059*
C24	0.75568 (16)	1.03779 (19)	0.23647 (17)	0.0747 (6)
H24A	0.7189	1.1066	0.2511	0.112*
H24B	0.7383	1.0385	0.1698	0.112*
H24C	0.8224	1.0589	0.2701	0.112*
C25	0.68278 (13)	0.68033 (18)	0.46619 (12)	0.0511 (4)
C26	0.56590 (17)	0.8428 (3)	0.4604 (2)	0.0891 (8)
H26A	0.5144	0.7906	0.4139	0.134*
H26B	0.5525	0.9408	0.4503	0.134*
H26C	0.5727	0.8178	0.5224	0.134*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0570 (7)	0.0447 (7)	0.0803 (9)	−0.0125 (6)	0.0413 (7)	−0.0052 (6)
O2	0.0555 (7)	0.0507 (7)	0.0624 (8)	−0.0152 (6)	0.0281 (6)	−0.0144 (6)
O3	0.0945 (10)	0.0629 (8)	0.1036 (11)	−0.0088 (8)	0.0734 (10)	0.0024 (8)
O4	0.0775 (9)	0.0521 (7)	0.0881 (10)	0.0029 (6)	0.0577 (8)	−0.0005 (7)
N1	0.0475 (8)	0.0464 (8)	0.0437 (8)	0.0061 (6)	0.0202 (6)	0.0065 (6)
N2	0.0579 (9)	0.0333 (7)	0.0603 (9)	−0.0026 (6)	0.0295 (7)	0.0028 (6)
C1	0.0604 (11)	0.0532 (11)	0.0598 (11)	0.0149 (9)	0.0223 (9)	0.0104 (9)
C2	0.0652 (11)	0.0552 (10)	0.0481 (10)	0.0046 (9)	0.0313 (9)	0.0099 (8)
C3	0.0543 (10)	0.0472 (9)	0.0452 (9)	−0.0055 (8)	0.0272 (8)	−0.0025 (7)
C4	0.0422 (8)	0.0358 (8)	0.0422 (8)	−0.0021 (6)	0.0225 (7)	−0.0013 (7)
C5	0.0387 (8)	0.0352 (8)	0.0410 (8)	−0.0005 (6)	0.0188 (7)	0.0005 (6)
C6	0.0364 (8)	0.0335 (8)	0.0546 (10)	0.0022 (6)	0.0207 (7)	0.0012 (7)
C7	0.0392 (8)	0.0320 (8)	0.0448 (9)	0.0037 (6)	0.0144 (7)	0.0016 (7)
C8	0.0502 (10)	0.0387 (9)	0.0521 (10)	−0.0008 (7)	0.0121 (8)	−0.0043 (8)
C9	0.0714 (12)	0.0467 (10)	0.0434 (10)	0.0045 (9)	0.0164 (9)	−0.0074 (8)
C10	0.0735 (12)	0.0481 (10)	0.0468 (10)	0.0071 (9)	0.0308 (9)	0.0015 (8)
C11	0.0523 (10)	0.0399 (8)	0.0421 (9)	0.0067 (7)	0.0231 (8)	0.0047 (7)
C12	0.0379 (8)	0.0331 (7)	0.0397 (8)	0.0048 (6)	0.0148 (7)	0.0037 (6)
C13	0.0362 (8)	0.0369 (8)	0.0411 (8)	0.0011 (6)	0.0176 (7)	0.0010 (7)
C14	0.0439 (9)	0.0511 (9)	0.0485 (9)	−0.0084 (7)	0.0219 (8)	−0.0058 (8)
C15	0.0484 (10)	0.0592 (11)	0.0664 (12)	−0.0132 (8)	0.0332 (9)	−0.0058 (9)
C16	0.0595 (11)	0.0573 (11)	0.0617 (11)	−0.0001 (9)	0.0402 (10)	0.0039 (9)
C17	0.0493 (9)	0.0376 (8)	0.0502 (9)	−0.0058 (7)	0.0290 (8)	−0.0091 (7)
C18	0.0411 (8)	0.0375 (8)	0.0454 (9)	0.0009 (6)	0.0241 (7)	−0.0023 (7)
C19	0.0502 (9)	0.0367 (8)	0.0483 (9)	0.0029 (7)	0.0273 (8)	−0.0026 (7)
C20	0.0653 (12)	0.0455 (10)	0.0572 (11)	0.0148 (9)	0.0274 (10)	0.0066 (8)
C21	0.0496 (10)	0.0622 (12)	0.0623 (12)	0.0147 (9)	0.0177 (9)	−0.0045 (10)
C22	0.0416 (10)	0.0616 (11)	0.0709 (12)	0.0012 (8)	0.0230 (9)	−0.0092 (10)
C23	0.0457 (9)	0.0454 (9)	0.0608 (11)	−0.0004 (7)	0.0277 (8)	−0.0006 (8)
C24	0.0924 (16)	0.0405 (10)	0.0951 (16)	−0.0103 (10)	0.0438 (13)	0.0119 (10)
C25	0.0649 (11)	0.0489 (10)	0.0522 (10)	−0.0087 (8)	0.0371 (9)	−0.0056 (8)
C26	0.0934 (17)	0.0816 (16)	0.127 (2)	0.0184 (13)	0.0803 (17)	0.0055 (14)

Geometric parameters (Å, º) top

O1—C6	1.2135 (18)	C9—C10	1.369 (3)
O2—C17	1.2178 (19)	C9—H9	0.9300
O3—C25	1.198 (2)	C10—C11	1.408 (2)
O4—C25	1.328 (2)	C10—H10	0.9300
O4—C26	1.436 (2)	C11—C12	1.402 (2)
N1—C2	1.453 (2)	C11—C16	1.408 (2)
N1—C1	1.459 (2)	C12—C13	1.407 (2)
N1—C5	1.4622 (19)	C13—C14	1.367 (2)
N2—C17	1.354 (2)	C14—C15	1.410 (2)
N2—C19	1.403 (2)	C14—H14	0.9300
N2—C24	1.455 (2)	C15—C16	1.360 (3)
C1—H1A	0.9600	C15—H15	0.9300
C1—H1B	0.9600	C16—H16	0.9300
C1—H1C	0.9600	C18—C23	1.379 (2)
C2—C3	1.513 (2)	C18—C19	1.389 (2)
C2—H2A	0.9700	C19—C20	1.374 (2)
C2—H2B	0.9700	C20—C21	1.379 (3)
C3—C25	1.494 (2)	C20—H20	0.9300
C3—C4	1.564 (2)	C21—C22	1.376 (3)
C3—H3	0.9800	C21—H21	0.9300
C4—C18	1.514 (2)	C22—C23	1.387 (2)
C4—C17	1.539 (2)	C22—H22	0.9300
C4—C5	1.590 (2)	C23—H23	0.9300
C5—C13	1.520 (2)	C24—H24A	0.9600
C5—C6	1.572 (2)	C24—H24B	0.9600
C6—C7	1.471 (2)	C24—H24C	0.9600
C7—C8	1.371 (2)	C26—H26A	0.9600
C7—C12	1.400 (2)	C26—H26B	0.9600
C8—C9	1.403 (2)	C26—H26C	0.9600
C8—H8	0.9300

C25—O4—C26	117.20 (15)	C12—C11—C16	116.49 (15)
C2—N1—C1	115.01 (14)	C10—C11—C16	127.37 (16)
C2—N1—C5	107.70 (12)	C7—C12—C11	122.73 (14)
C1—N1—C5	115.53 (13)	C7—C12—C13	113.46 (13)
C17—N2—C19	111.21 (13)	C11—C12—C13	123.65 (14)
C17—N2—C24	123.77 (15)	C14—C13—C12	118.01 (14)
C19—N2—C24	124.40 (15)	C14—C13—C5	132.55 (14)
N1—C1—H1A	109.5	C12—C13—C5	109.14 (12)
N1—C1—H1B	109.5	C13—C14—C15	119.08 (15)
H1A—C1—H1B	109.5	C13—C14—H14	120.5
N1—C1—H1C	109.5	C15—C14—H14	120.5
H1A—C1—H1C	109.5	C16—C15—C14	122.79 (16)
H1B—C1—H1C	109.5	C16—C15—H15	118.6
N1—C2—C3	102.59 (13)	C14—C15—H15	118.6
N1—C2—H2A	111.2	C15—C16—C11	119.94 (15)
C3—C2—H2A	111.2	C15—C16—H16	120.0
N1—C2—H2B	111.2	C11—C16—H16	120.0
C3—C2—H2B	111.2	O2—C17—N2	125.31 (15)
H2A—C2—H2B	109.2	O2—C17—C4	126.49 (15)
C25—C3—C2	114.31 (14)	N2—C17—C4	108.19 (13)
C25—C3—C4	114.51 (14)	C23—C18—C19	118.95 (15)
C2—C3—C4	105.51 (13)	C23—C18—C4	132.22 (14)
C25—C3—H3	107.4	C19—C18—C4	108.63 (13)
C2—C3—H3	107.4	C20—C19—C18	122.52 (16)
C4—C3—H3	107.4	C20—C19—N2	127.77 (16)
C18—C4—C17	101.45 (12)	C18—C19—N2	109.61 (14)
C18—C4—C3	117.85 (12)	C19—C20—C21	117.63 (17)
C17—C4—C3	108.74 (12)	C19—C20—H20	121.2
C18—C4—C5	115.01 (12)	C21—C20—H20	121.2
C17—C4—C5	110.31 (12)	C22—C21—C20	121.07 (17)
C3—C4—C5	103.43 (12)	C22—C21—H21	119.5
N1—C5—C13	111.32 (12)	C20—C21—H21	119.5
N1—C5—C6	112.02 (12)	C21—C22—C23	120.68 (17)
C13—C5—C6	101.67 (12)	C21—C22—H22	119.7
N1—C5—C4	102.87 (11)	C23—C22—H22	119.7
C13—C5—C4	117.40 (12)	C18—C23—C22	119.14 (16)
C6—C5—C4	111.90 (11)	C18—C23—H23	120.4
O1—C6—C7	126.75 (15)	C22—C23—H23	120.4
O1—C6—C5	124.52 (14)	N2—C24—H24A	109.5
C7—C6—C5	108.34 (12)	N2—C24—H24B	109.5
C8—C7—C12	119.87 (15)	H24A—C24—H24B	109.5
C8—C7—C6	132.72 (15)	N2—C24—H24C	109.5
C12—C7—C6	107.13 (13)	H24A—C24—H24C	109.5
C7—C8—C9	118.06 (16)	H24B—C24—H24C	109.5
C7—C8—H8	121.0	O3—C25—O4	123.53 (17)
C9—C8—H8	121.0	O3—C25—C3	125.34 (17)
C10—C9—C8	122.29 (16)	O4—C25—C3	111.12 (14)
C10—C9—H9	118.9	O4—C26—H26A	109.5
C8—C9—H9	118.9	O4—C26—H26B	109.5
C9—C10—C11	120.90 (16)	H26A—C26—H26B	109.5
C9—C10—H10	119.5	O4—C26—H26C	109.5
C11—C10—H10	119.5	H26A—C26—H26C	109.5
C12—C11—C10	116.09 (15)	H26B—C26—H26C	109.5

C1—N1—C2—C3	−174.54 (14)	C7—C12—C13—C5	−0.36 (17)
C5—N1—C2—C3	−44.14 (16)	C11—C12—C13—C5	−175.79 (13)
N1—C2—C3—C25	158.48 (14)	N1—C5—C13—C14	−50.7 (2)
N1—C2—C3—C4	31.78 (17)	C6—C5—C13—C14	−170.18 (17)
C25—C3—C4—C18	−8.3 (2)	C4—C5—C13—C14	67.4 (2)
C2—C3—C4—C18	118.29 (15)	N1—C5—C13—C12	122.71 (13)
C25—C3—C4—C17	106.29 (16)	C6—C5—C13—C12	3.27 (15)
C2—C3—C4—C17	−127.12 (14)	C4—C5—C13—C12	−119.15 (14)
C25—C3—C4—C5	−136.46 (14)	C12—C13—C14—C15	2.0 (2)
C2—C3—C4—C5	−9.87 (16)	C5—C13—C14—C15	174.98 (16)
C2—N1—C5—C13	163.81 (13)	C13—C14—C15—C16	−1.2 (3)
C1—N1—C5—C13	−66.09 (17)	C14—C15—C16—C11	−0.5 (3)
C2—N1—C5—C6	−83.11 (15)	C12—C11—C16—C15	1.3 (2)
C1—N1—C5—C6	47.00 (18)	C10—C11—C16—C15	−176.25 (17)
C2—N1—C5—C4	37.23 (15)	C19—N2—C17—O2	−169.50 (15)
C1—N1—C5—C4	167.34 (13)	C24—N2—C17—O2	1.8 (3)
C18—C4—C5—N1	−145.28 (12)	C19—N2—C17—C4	9.62 (17)
C17—C4—C5—N1	100.76 (14)	C24—N2—C17—C4	−179.04 (16)
C3—C4—C5—N1	−15.38 (14)	C18—C4—C17—O2	169.98 (15)
C18—C4—C5—C13	92.14 (15)	C3—C4—C17—O2	45.1 (2)
C17—C4—C5—C13	−21.82 (18)	C5—C4—C17—O2	−67.68 (19)
C3—C4—C5—C13	−137.96 (13)	C18—C4—C17—N2	−9.13 (15)
C18—C4—C5—C6	−24.86 (17)	C3—C4—C17—N2	−134.01 (13)
C17—C4—C5—C6	−138.82 (13)	C5—C4—C17—N2	113.21 (14)
C3—C4—C5—C6	105.04 (14)	C17—C4—C18—C23	−169.12 (16)
N1—C5—C6—O1	49.29 (19)	C3—C4—C18—C23	−50.6 (2)
C13—C5—C6—O1	168.23 (14)	C5—C4—C18—C23	71.8 (2)
C4—C5—C6—O1	−65.65 (19)	C17—C4—C18—C19	5.61 (15)
N1—C5—C6—C7	−123.94 (13)	C3—C4—C18—C19	124.14 (14)
C13—C5—C6—C7	−5.00 (15)	C5—C4—C18—C19	−113.43 (14)
C4—C5—C6—C7	121.13 (13)	C23—C18—C19—C20	−1.4 (2)
O1—C6—C7—C8	5.6 (3)	C4—C18—C19—C20	−176.94 (15)
C5—C6—C7—C8	178.65 (16)	C23—C18—C19—N2	175.13 (14)
O1—C6—C7—C12	−168.02 (15)	C4—C18—C19—N2	−0.41 (17)
C5—C6—C7—C12	5.01 (16)	C17—N2—C19—C20	170.31 (16)
C12—C7—C8—C9	0.0 (2)	C24—N2—C19—C20	−1.0 (3)
C6—C7—C8—C9	−172.97 (16)	C17—N2—C19—C18	−5.99 (18)
C7—C8—C9—C10	1.7 (3)	C24—N2—C19—C18	−177.26 (16)
C8—C9—C10—C11	−1.4 (3)	C18—C19—C20—C21	1.0 (2)
C9—C10—C11—C12	−0.6 (2)	N2—C19—C20—C21	−174.81 (16)
C9—C10—C11—C16	176.92 (17)	C19—C20—C21—C22	0.1 (3)
C8—C7—C12—C11	−2.1 (2)	C20—C21—C22—C23	−0.8 (3)
C6—C7—C12—C11	172.48 (13)	C19—C18—C23—C22	0.6 (2)
C8—C7—C12—C13	−177.61 (13)	C4—C18—C23—C22	174.91 (16)
C6—C7—C12—C13	−3.00 (17)	C21—C22—C23—C18	0.4 (3)
C10—C11—C12—C7	2.4 (2)	C26—O4—C25—O3	−3.1 (3)
C16—C11—C12—C7	−175.42 (14)	C26—O4—C25—C3	176.22 (17)
C10—C11—C12—C13	177.41 (14)	C2—C3—C25—O3	−7.5 (3)
C16—C11—C12—C13	−0.4 (2)	C4—C3—C25—O3	114.4 (2)
C7—C12—C13—C14	174.18 (14)	C2—C3—C25—O4	173.17 (15)
C11—C12—C13—C14	−1.3 (2)	C4—C3—C25—O4	−64.93 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2ⁱ	0.93	2.60	3.268 (2)	130

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₂N₂O₄
M_r	426.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.4839 (4), 9.5832 (2), 15.6375 (4)
β (°)	115.184 (1)
V (Å³)	2099.81 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.22 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.977, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	19264, 4057, 3017
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.613

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.103, 1.03
No. of reflections	4057
No. of parameters	292
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.17

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2ⁱ	0.93	2.60	3.268 (2)	129.6

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

ASP thanks the University Grants Commission, India, for a Minor Research Project.

References

Bruker (2008). APEX2, SADABS 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
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals 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
Varma, A., Kolli, B. K., Paul, J., Saxena, S. & Konig, H. (1994). FEMS Microbiol. Rev. 15, 9–28. CAS Google Scholar
Wei, A. C., Ali, M. A., Choon, T. S., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o1340–o1341. CSD CrossRef IUCr Journals Google Scholar
Wiltz, B. A., Henderson, G. & Chen, J. (1998). Environ. Entomol. 27, 936–940. CAS Google Scholar
Wright, M. S., Lax, A. R., Henderson, G. & Chen, J. A. (2000). Mycologia, 92, 42–45. Web of Science CrossRef CAS Google Scholar

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

rac-Methyl (1R,3′S)-1′,1′′-di­methyl-2,2′′-dioxo-2H-di­spiro­[ace­naphthyl­ene-1,2′-pyrrolidine-3′,3′′-indoline]-4′-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

rac-Methyl (1R,3′S)-1′,1′′-dimethyl-2,2′′-dioxo-2H-dispiro[acenaphthylene-1,2′-pyrrolidine-3′,3′′-indoline]-4′-carboxylate