A diastereomer of 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.; Kannan, P.S.; Reddy, B.S.R.; SubbiahPandi, A.

doi:10.1107/S1600536813004868

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o441

doi:10.1107/S1600536813004868

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A diastereomer of methyl (1R,3′S)-1′,1′′-dimethyl-2,2′′-dioxo-2H-dispiro[acenaphthylene-1,2′-pyrrolidine-3′,3′′-indoline]-4′-carboxylate

Gnanavelu Ganesh,^a PanneerSelvam Yuvaraj,^b Piskala Subburaman Kannan,^a Boreddy Siva Rami Reddy ^b and Arunachalathevar 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 January 2013; accepted 19 February 2013; online 23 February 2013)

In the title compound, C₂₆H₂₂N₂O₄, the central pyrrolidine ring adopts a twist conformation and the cyclopentane ring of the dihydroacenapthylene group adopts an envelope conformation with the spiro C atom as the flap. The naphthalene ring system of the dihydroacenaphthylene group forms dihedral angles of 83.4 (9) and 61.3 (7)°, respectively, with the mean planes of the pyrrolidine and indole rings. The crystal packing is stabilized by intermolecular C—H⋯O hydrogen bonds. The title compound is a diastereomer of a previously reported structure.

Related literature

For background literature and the previously reported diastereomer, see: Ganesh et al. (2013 ). For a related structure, see: Wei et al. (2012 ). For information on ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₆H₂₂N₂O₄
M_r = 426.46
Orthorhombic, P b c n
a = 27.2997 (15) Å
b = 9.7923 (6) Å
c = 15.8557 (10) Å
V = 4238.7 (4) Å³
Z = 8
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 = 0.978, T_max = 0.983
23813 measured reflections
5039 independent reflections
3022 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.135
S = 1.02
5039 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
C1—H1B⋯O3ⁱ	0.96	2.48	3.299 (3)	143
C20—H20⋯O3ⁱⁱ	0.93	2.59	3.403 (3)	146
Symmetry codes: (i) $[x, -y, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT; 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/S1600536813004868/bt6885sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813004868/bt6885Isup2.hkl

checkCIF report

Comment top

We have recently reported the structure of a diastereomer of the title compound (Ganesh et al., 2013). Here we report the structural details of its diastereomer.

X–Ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The geometry of the acenaphthylene and pyrrolidine ring systems are comparable with the related structure (Wei et al., 2012). The sum of the angles at N1 [339.5 (1)°] and N2 [359.8 (1)°] of the pyrrolidine rings are in accordance with sp³ and sp² hybridization. The naphthalene ring system [C7–C16] of the dihydroacenaphthylene group forms dihedral angles of 83.4 (9) and 61.3 (7)° with the central pyrrolidine ring [N1/C2–C5] and the indole ring [N2/C4/C17–C23]. The central pyrrolidine also makes a dihedral angle of 87.6 (9)° with the indole which shows that these two rings are almost perpendicular with each other.

The pyrrolidine rings [N1/C2-C5] adopts a twist conformation, on C4 and C5 atoms with puckering parameters of q₂ = 0.470 (2) Å, ϕ = 128.1 (2) (Cremer & Pople, 1975). The cyclopentane ring [C5-C7/C12-C13] in the dihydroacenapthylene group adopts an envelope conformation [q₂ = 0.074 (9)(2) Å and ϕ = 173.3 (2)°], and with atom C5 deviating by 0.044 (2) Å from the least-squares plane passing through the remaining four atoms (C13/C12/C7/C6) of that ring. In the crystal, the molecules are linked by intermolecular C20-H20···O3 and C1-H1B···O3 hydrogen bonds Fig. 2.

Related literature top

For background literature and the previously reported diastereomer, see: Ganesh et al. (2013). For a related structure, see: Wei et al. (2012). For information on ring conformations, see: Cremer & Pople (1975).

Experimental top

A mixture of 1 eq of (E)-methyl 2-(1-methyl-2-oxoindolin-3-ylidene) acetate, 1 eq of isatin and 1.5 eq of acenaphthylene-1,2-dione were dissolved in acetonitrile. This reaction mixture was refluxed at 353K for 8 hours. The reaction mixture was monitored for completion by thin layer chromatography. Upon completion, the 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.
	Fig. 2. The molecular packing viewed down the b axis. Dashed lines shows the intermolecular C-H···O hydrogen bonds.

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) = 1792
M_r = 426.46	D_x = 1.337 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 5039 reflections
a = 27.2997 (15) Å	θ = 1.5–27.9°
b = 9.7923 (6) Å	µ = 0.09 mm⁻¹
c = 15.8557 (10) Å	T = 293 K
V = 4238.7 (4) Å³	Block, colourless
Z = 8	0.25 × 0.22 × 0.19 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	5039 independent reflections
Radiation source: fine-focus sealed tube	3022 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω and ϕ scans	θ_max = 27.9°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −35→31
T_min = 0.978, T_max = 0.983	k = −12→11
23813 measured reflections	l = −18→20

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0531P)² + 1.3523P] where P = (F_o² + 2F_c²)/3
5039 reflections	(Δ/σ)_max = 0.002
292 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₆H₂₂N₂O₄	V = 4238.7 (4) Å³
M_r = 426.46	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 27.2997 (15) Å	µ = 0.09 mm⁻¹
b = 9.7923 (6) Å	T = 293 K
c = 15.8557 (10) Å	0.25 × 0.22 × 0.19 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	5039 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3022 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.983	R_int = 0.033
23813 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.02	Δρ_max = 0.17 e Å⁻³
5039 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
C1	0.55248 (7)	−0.08437 (18)	0.02663 (15)	0.0583 (6)
H1A	0.5740	−0.1607	0.0354	0.087*
H1B	0.5527	−0.0596	−0.0320	0.087*
H1C	0.5198	−0.1088	0.0432	0.087*
C2	0.57113 (7)	0.0054 (2)	0.16787 (14)	0.0543 (5)
H2A	0.5784	−0.0897	0.1794	0.065*
H2B	0.5402	0.0285	0.1943	0.065*
C3	0.61210 (7)	0.09760 (19)	0.20075 (12)	0.0463 (5)
H3	0.6412	0.0409	0.2098	0.056*
C4	0.62250 (6)	0.19357 (17)	0.12618 (11)	0.0380 (4)
C5	0.61516 (6)	0.09285 (16)	0.05178 (12)	0.0380 (4)
C6	0.65873 (6)	−0.01367 (18)	0.04464 (13)	0.0454 (5)
C7	0.68374 (6)	0.0100 (2)	−0.03587 (13)	0.0492 (5)
C8	0.72342 (7)	−0.0500 (2)	−0.07337 (16)	0.0672 (6)
H8	0.7404	−0.1202	−0.0469	0.081*
C9	0.73756 (9)	−0.0022 (3)	−0.15287 (18)	0.0842 (8)
H9	0.7652	−0.0399	−0.1781	0.101*
C10	0.71257 (9)	0.0973 (3)	−0.19492 (16)	0.0778 (7)
H10	0.7234	0.1258	−0.2477	0.093*
C11	0.67050 (8)	0.1574 (2)	−0.15918 (14)	0.0573 (5)
C12	0.65758 (7)	0.11197 (19)	−0.07840 (12)	0.0444 (4)
C13	0.61607 (6)	0.15884 (17)	−0.03457 (12)	0.0401 (4)
C14	0.58614 (7)	0.24994 (19)	−0.07357 (13)	0.0500 (5)
H14	0.5581	0.2818	−0.0467	0.060*
C15	0.59812 (9)	0.2955 (2)	−0.15527 (14)	0.0617 (6)
H15	0.5773	0.3571	−0.1819	0.074*
C16	0.63878 (9)	0.2529 (2)	−0.19651 (14)	0.0661 (6)
H16	0.6458	0.2872	−0.2499	0.079*
C17	0.67325 (6)	0.26047 (19)	0.12476 (12)	0.0413 (4)
C18	0.61710 (6)	0.43187 (17)	0.11591 (11)	0.0368 (4)
C19	0.58897 (6)	0.31498 (16)	0.12240 (11)	0.0359 (4)
C20	0.53874 (6)	0.32524 (19)	0.12696 (13)	0.0479 (5)
H20	0.5193	0.2477	0.1322	0.058*
C21	0.51788 (7)	0.4538 (2)	0.12360 (16)	0.0627 (6)
H21	0.4840	0.4627	0.1268	0.075*
C22	0.54625 (8)	0.5680 (2)	0.11568 (16)	0.0644 (6)
H22	0.5313	0.6532	0.1132	0.077*
C23	0.59676 (7)	0.55977 (19)	0.11128 (13)	0.0501 (5)
H23	0.6161	0.6374	0.1054	0.060*
C24	0.70630 (7)	0.4956 (2)	0.11344 (14)	0.0560 (5)
H24A	0.7370	0.4487	0.1084	0.084*
H24B	0.7060	0.5481	0.1646	0.084*
H24C	0.7020	0.5554	0.0660	0.084*
C25	0.60097 (8)	0.1700 (2)	0.28144 (14)	0.0548 (5)
C26	0.63246 (11)	0.3314 (3)	0.37857 (16)	0.0865 (8)
H26A	0.5988	0.3558	0.3876	0.130*
H26B	0.6520	0.4127	0.3756	0.130*
H26C	0.6436	0.2755	0.4245	0.130*
N1	0.56904 (5)	0.03024 (14)	0.07673 (10)	0.0434 (4)
N2	0.66700 (5)	0.39740 (15)	0.11545 (9)	0.0403 (4)
O1	0.66576 (5)	−0.10603 (14)	0.09387 (10)	0.0617 (4)
O2	0.71209 (5)	0.20188 (14)	0.12955 (10)	0.0625 (4)
O3	0.56571 (6)	0.1529 (2)	0.32417 (11)	0.0878 (6)
O4	0.63683 (6)	0.25647 (16)	0.30058 (10)	0.0693 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0490 (11)	0.0381 (10)	0.0879 (17)	−0.0046 (9)	−0.0040 (11)	0.0022 (10)
C2	0.0531 (12)	0.0480 (11)	0.0617 (14)	−0.0003 (10)	0.0105 (10)	0.0145 (10)
C3	0.0414 (10)	0.0462 (10)	0.0512 (12)	0.0086 (8)	0.0057 (9)	0.0108 (9)
C4	0.0278 (8)	0.0392 (9)	0.0470 (11)	0.0050 (7)	0.0022 (7)	0.0035 (8)
C5	0.0293 (8)	0.0356 (8)	0.0491 (11)	0.0030 (7)	0.0016 (8)	0.0035 (8)
C6	0.0369 (9)	0.0405 (10)	0.0588 (12)	0.0054 (8)	−0.0038 (9)	−0.0033 (9)
C7	0.0354 (9)	0.0547 (11)	0.0576 (13)	0.0022 (9)	−0.0015 (9)	−0.0152 (10)
C8	0.0456 (12)	0.0851 (16)	0.0708 (16)	0.0130 (11)	0.0014 (11)	−0.0249 (13)
C9	0.0501 (14)	0.130 (2)	0.0731 (18)	0.0053 (16)	0.0132 (13)	−0.0356 (18)
C10	0.0615 (15)	0.118 (2)	0.0535 (15)	−0.0135 (15)	0.0146 (12)	−0.0166 (15)
C11	0.0541 (12)	0.0691 (14)	0.0487 (13)	−0.0160 (11)	0.0033 (10)	−0.0122 (11)
C12	0.0383 (10)	0.0490 (10)	0.0460 (11)	−0.0077 (8)	−0.0008 (8)	−0.0098 (9)
C13	0.0346 (9)	0.0391 (9)	0.0465 (11)	−0.0042 (7)	−0.0007 (8)	−0.0018 (8)
C14	0.0522 (11)	0.0468 (10)	0.0510 (12)	0.0023 (9)	−0.0042 (9)	0.0033 (9)
C15	0.0739 (15)	0.0565 (12)	0.0546 (14)	−0.0030 (11)	−0.0114 (12)	0.0076 (10)
C16	0.0824 (16)	0.0717 (15)	0.0443 (13)	−0.0195 (14)	−0.0002 (12)	0.0046 (11)
C17	0.0298 (9)	0.0503 (10)	0.0439 (11)	0.0042 (8)	0.0005 (8)	−0.0039 (8)
C18	0.0312 (9)	0.0406 (9)	0.0388 (10)	0.0001 (7)	−0.0009 (7)	0.0022 (7)
C19	0.0302 (8)	0.0364 (9)	0.0410 (10)	0.0028 (7)	0.0035 (7)	0.0027 (7)
C20	0.0287 (9)	0.0435 (10)	0.0716 (14)	0.0002 (8)	0.0057 (9)	0.0043 (9)
C21	0.0327 (10)	0.0522 (12)	0.1033 (19)	0.0103 (9)	0.0043 (11)	0.0031 (12)
C22	0.0507 (12)	0.0411 (11)	0.1013 (19)	0.0123 (10)	−0.0040 (12)	0.0057 (11)
C23	0.0472 (11)	0.0385 (10)	0.0646 (14)	−0.0027 (8)	−0.0034 (10)	0.0049 (9)
C24	0.0359 (10)	0.0637 (12)	0.0684 (15)	−0.0142 (9)	0.0005 (10)	−0.0036 (11)
C25	0.0512 (12)	0.0612 (13)	0.0522 (13)	0.0139 (10)	0.0039 (10)	0.0137 (10)
C26	0.113 (2)	0.0783 (17)	0.0680 (17)	0.0095 (16)	0.0000 (16)	−0.0145 (14)
N1	0.0343 (8)	0.0364 (8)	0.0595 (10)	−0.0005 (6)	0.0051 (7)	0.0061 (7)
N2	0.0283 (7)	0.0451 (8)	0.0474 (9)	−0.0041 (6)	−0.0004 (6)	0.0007 (7)
O1	0.0559 (9)	0.0494 (8)	0.0797 (11)	0.0188 (7)	0.0000 (8)	0.0083 (8)
O2	0.0301 (7)	0.0664 (9)	0.0908 (12)	0.0120 (6)	−0.0030 (7)	−0.0080 (8)
O3	0.0700 (11)	0.1265 (15)	0.0668 (11)	0.0017 (10)	0.0238 (9)	−0.0047 (11)
O4	0.0766 (11)	0.0749 (10)	0.0566 (10)	−0.0028 (9)	0.0069 (8)	−0.0051 (8)

Geometric parameters (Å, º) top

C1—N1	1.447 (2)	C13—C14	1.359 (2)
C1—H1A	0.9600	C14—C15	1.408 (3)
C1—H1B	0.9600	C14—H14	0.9300
C1—H1C	0.9600	C15—C16	1.354 (3)
C2—N1	1.467 (3)	C15—H15	0.9300
C2—C3	1.529 (3)	C16—H16	0.9300
C2—H2A	0.9700	C17—O2	1.208 (2)
C2—H2B	0.9700	C17—N2	1.360 (2)
C3—C25	1.494 (3)	C18—C23	1.372 (2)
C3—C4	1.537 (2)	C18—C19	1.382 (2)
C3—H3	0.9800	C18—N2	1.403 (2)
C4—C19	1.502 (2)	C19—C20	1.377 (2)
C4—C17	1.533 (2)	C20—C21	1.383 (3)
C4—C5	1.551 (2)	C20—H20	0.9300
C5—N1	1.455 (2)	C21—C22	1.366 (3)
C5—C13	1.514 (2)	C21—H21	0.9300
C5—C6	1.586 (2)	C22—C23	1.383 (3)
C6—O1	1.210 (2)	C22—H22	0.9300
C6—C7	1.466 (3)	C23—H23	0.9300
C7—C8	1.368 (3)	C24—N2	1.441 (2)
C7—C12	1.401 (3)	C24—H24A	0.9600
C8—C9	1.399 (4)	C24—H24B	0.9600
C8—H8	0.9300	C24—H24C	0.9600
C9—C10	1.364 (4)	C25—O3	1.189 (2)
C9—H9	0.9300	C25—O4	1.330 (3)
C10—C11	1.410 (3)	C26—O4	1.443 (3)
C10—H10	0.9300	C26—H26A	0.9600
C11—C12	1.401 (3)	C26—H26B	0.9600
C11—C16	1.406 (3)	C26—H26C	0.9600
C12—C13	1.406 (2)

N1—C1—H1A	109.5	C12—C13—C5	108.70 (15)
N1—C1—H1B	109.5	C13—C14—C15	119.1 (2)
H1A—C1—H1B	109.5	C13—C14—H14	120.4
N1—C1—H1C	109.5	C15—C14—H14	120.4
H1A—C1—H1C	109.5	C16—C15—C14	122.5 (2)
H1B—C1—H1C	109.5	C16—C15—H15	118.8
N1—C2—C3	105.47 (15)	C14—C15—H15	118.8
N1—C2—H2A	110.6	C15—C16—C11	120.4 (2)
C3—C2—H2A	110.6	C15—C16—H16	119.8
N1—C2—H2B	110.6	C11—C16—H16	119.8
C3—C2—H2B	110.6	O2—C17—N2	125.81 (17)
H2A—C2—H2B	108.8	O2—C17—C4	126.13 (17)
C25—C3—C2	115.06 (17)	N2—C17—C4	108.05 (14)
C25—C3—C4	113.98 (16)	C23—C18—C19	122.33 (16)
C2—C3—C4	103.53 (15)	C23—C18—N2	127.75 (16)
C25—C3—H3	108.0	C19—C18—N2	109.91 (14)
C2—C3—H3	108.0	C20—C19—C18	119.80 (15)
C4—C3—H3	108.0	C20—C19—C4	131.52 (15)
C19—C4—C17	102.25 (13)	C18—C19—C4	108.64 (14)
C19—C4—C3	113.70 (14)	C19—C20—C21	118.33 (17)
C17—C4—C3	116.09 (15)	C19—C20—H20	120.8
C19—C4—C5	113.23 (14)	C21—C20—H20	120.8
C17—C4—C5	112.19 (14)	C22—C21—C20	121.03 (18)
C3—C4—C5	99.93 (13)	C22—C21—H21	119.5
N1—C5—C13	116.08 (14)	C20—C21—H21	119.5
N1—C5—C4	99.96 (13)	C21—C22—C23	121.47 (18)
C13—C5—C4	114.48 (13)	C21—C22—H22	119.3
N1—C5—C6	113.03 (13)	C23—C22—H22	119.3
C13—C5—C6	101.76 (14)	C18—C23—C22	117.02 (18)
C4—C5—C6	112.06 (14)	C18—C23—H23	121.5
O1—C6—C7	127.30 (17)	C22—C23—H23	121.5
O1—C6—C5	124.36 (17)	N2—C24—H24A	109.5
C7—C6—C5	107.91 (15)	N2—C24—H24B	109.5
C8—C7—C12	120.0 (2)	H24A—C24—H24B	109.5
C8—C7—C6	132.8 (2)	N2—C24—H24C	109.5
C12—C7—C6	107.11 (16)	H24A—C24—H24C	109.5
C7—C8—C9	117.8 (2)	H24B—C24—H24C	109.5
C7—C8—H8	121.1	O3—C25—O4	123.7 (2)
C9—C8—H8	121.1	O3—C25—C3	125.9 (2)
C10—C9—C8	122.8 (2)	O4—C25—C3	110.38 (17)
C10—C9—H9	118.6	O4—C26—H26A	109.5
C8—C9—H9	118.6	O4—C26—H26B	109.5
C9—C10—C11	120.6 (2)	H26A—C26—H26B	109.5
C9—C10—H10	119.7	O4—C26—H26C	109.5
C11—C10—H10	119.7	H26A—C26—H26C	109.5
C12—C11—C16	116.18 (19)	H26B—C26—H26C	109.5
C12—C11—C10	116.1 (2)	C1—N1—C5	116.59 (15)
C16—C11—C10	127.6 (2)	C1—N1—C2	115.12 (15)
C7—C12—C11	122.55 (18)	C5—N1—C2	107.69 (14)
C7—C12—C13	113.93 (18)	C17—N2—C18	111.00 (14)
C11—C12—C13	123.44 (19)	C17—N2—C24	124.54 (15)
C14—C13—C12	118.29 (18)	C18—N2—C24	124.22 (15)
C14—C13—C5	133.00 (17)	C25—O4—C26	117.31 (19)

N1—C2—C3—C25	137.57 (16)	C12—C13—C14—C15	−1.0 (3)
N1—C2—C3—C4	12.55 (18)	C5—C13—C14—C15	178.08 (18)
C25—C3—C4—C19	−41.3 (2)	C13—C14—C15—C16	−0.7 (3)
C2—C3—C4—C19	84.45 (18)	C14—C15—C16—C11	1.5 (3)
C25—C3—C4—C17	77.0 (2)	C12—C11—C16—C15	−0.6 (3)
C2—C3—C4—C17	−157.33 (15)	C10—C11—C16—C15	176.3 (2)
C25—C3—C4—C5	−162.21 (15)	C19—C4—C17—O2	177.45 (19)
C2—C3—C4—C5	−36.50 (16)	C3—C4—C17—O2	53.1 (3)
C19—C4—C5—N1	−73.87 (16)	C5—C4—C17—O2	−60.9 (2)
C17—C4—C5—N1	171.02 (13)	C19—C4—C17—N2	−3.77 (19)
C3—C4—C5—N1	47.41 (14)	C3—C4—C17—N2	−128.12 (16)
C19—C4—C5—C13	50.91 (19)	C5—C4—C17—N2	117.86 (16)
C17—C4—C5—C13	−64.20 (18)	C23—C18—C19—C20	−2.0 (3)
C3—C4—C5—C13	172.20 (14)	N2—C18—C19—C20	177.74 (17)
C19—C4—C5—C6	166.14 (14)	C23—C18—C19—C4	−179.96 (17)
C17—C4—C5—C6	51.03 (19)	N2—C18—C19—C4	−0.3 (2)
C3—C4—C5—C6	−72.58 (16)	C17—C4—C19—C20	−175.3 (2)
N1—C5—C6—O1	−40.9 (3)	C3—C4—C19—C20	−49.4 (3)
C13—C5—C6—O1	−166.14 (18)	C5—C4—C19—C20	63.8 (3)
C4—C5—C6—O1	71.1 (2)	C17—C4—C19—C18	2.39 (18)
N1—C5—C6—C7	131.98 (16)	C3—C4—C19—C18	128.31 (16)
C13—C5—C6—C7	6.77 (17)	C5—C4—C19—C18	−118.52 (16)
C4—C5—C6—C7	−115.98 (16)	C18—C19—C20—C21	0.9 (3)
O1—C6—C7—C8	−8.3 (4)	C4—C19—C20—C21	178.4 (2)
C5—C6—C7—C8	179.0 (2)	C19—C20—C21—C22	0.2 (3)
O1—C6—C7—C12	168.86 (19)	C20—C21—C22—C23	−0.4 (4)
C5—C6—C7—C12	−3.79 (19)	C19—C18—C23—C22	1.7 (3)
C12—C7—C8—C9	2.4 (3)	N2—C18—C23—C22	−177.93 (19)
C6—C7—C8—C9	179.3 (2)	C21—C22—C23—C18	−0.5 (3)
C7—C8—C9—C10	−2.3 (4)	C2—C3—C25—O3	6.7 (3)
C8—C9—C10—C11	0.0 (4)	C4—C3—C25—O3	126.1 (2)
C9—C10—C11—C12	2.0 (3)	C2—C3—C25—O4	−174.36 (16)
C9—C10—C11—C16	−174.9 (2)	C4—C3—C25—O4	−55.0 (2)
C8—C7—C12—C11	−0.4 (3)	C13—C5—N1—C1	63.6 (2)
C6—C7—C12—C11	−178.03 (17)	C4—C5—N1—C1	−172.74 (14)
C8—C7—C12—C13	176.48 (17)	C6—C5—N1—C1	−53.5 (2)
C6—C7—C12—C13	−1.1 (2)	C13—C5—N1—C2	−165.25 (15)
C16—C11—C12—C7	175.42 (18)	C4—C5—N1—C2	−41.59 (16)
C10—C11—C12—C7	−1.8 (3)	C6—C5—N1—C2	77.70 (18)
C16—C11—C12—C13	−1.2 (3)	C3—C2—N1—C1	150.60 (15)
C10—C11—C12—C13	−178.42 (18)	C3—C2—N1—C5	18.64 (18)
C7—C12—C13—C14	−174.87 (16)	O2—C17—N2—C18	−177.33 (18)
C11—C12—C13—C14	2.0 (3)	C4—C17—N2—C18	3.9 (2)
C7—C12—C13—C5	5.8 (2)	O2—C17—N2—C24	−2.8 (3)
C11—C12—C13—C5	−177.31 (16)	C4—C17—N2—C24	178.40 (16)
N1—C5—C13—C14	50.3 (3)	C23—C18—N2—C17	177.32 (19)
C4—C5—C13—C14	−65.5 (2)	C19—C18—N2—C17	−2.4 (2)
C6—C5—C13—C14	173.43 (19)	C23—C18—N2—C24	2.8 (3)
N1—C5—C13—C12	−130.55 (15)	C19—C18—N2—C24	−176.90 (17)
C4—C5—C13—C12	113.69 (15)	O3—C25—O4—C26	1.0 (3)
C6—C5—C13—C12	−7.40 (17)	C3—C25—O4—C26	−177.94 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O3ⁱ	0.96	2.48	3.299 (3)	143
C20—H20···O3ⁱⁱ	0.93	2.59	3.403 (3)	146

Symmetry codes: (i) x, −y, z−1/2; (ii) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₂N₂O₄
M_r	426.46
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	293
a, b, c (Å)	27.2997 (15), 9.7923 (6), 15.8557 (10)
V (Å³)	4238.7 (4)
Z	8
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	0.978, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	23813, 5039, 3022
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.135, 1.02
No. of reflections	5039
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
C1—H1B···O3ⁱ	0.96	2.48	3.299 (3)	142.8
C20—H20···O3ⁱⁱ	0.93	2.59	3.403 (3)	145.7

Symmetry codes: (i) x, −y, z−1/2; (ii) −x+1, y, −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
Ganesh, G., Yuvaraj, P. S., Divakara, C., Reddy, B. S. R. & SubbiahPandi, A. (2013). Acta Cryst. E69, o235. CSD CrossRef 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
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

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Volume 69| Part 3| March 2013| Page o441

doi:10.1107/S1600536813004868

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

A diastereomer of 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

A diastereomer of methyl (1R,3′S)-1′,1′′-dimethyl-2,2′′-dioxo-2H-dispiro[acenaphthylene-1,2′-pyrrolidine-3′,3′′-indoline]-4′-carboxylate