5,6-Dimeth­oxy-4′,5′-diphenyl­indane-2-spiro-3′-pyrrolidine-2′-spiro-3′′-indoline-1,2′′-dione

Ali, M.A.; Ismail, R.; Tan, S.C.; Yeap, C.S.; Fun, H.-K.

doi:10.1107/S1600536810035865

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2533-o2534

doi:10.1107/S1600536810035865

Open

access

5,6-Dimethoxy-4′,5′-diphenylindane-2-spiro-3′-pyrrolidine-2′-spiro-3′′-indoline-1,2′′-dione

Mohamed Ashraf Ali,^a Rusli Ismail,^a Soo Choon Tan,^a Chin Sing Yeap ^b ‡ and Hoong-Kun Fun ^b ^*§

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 30 August 2010; accepted 7 September 2010; online 11 September 2010)

In the title compound, C₃₃H₂₈N₂O₄, the central pyrrolidine ring adopts a half-chair conformation. Both the indolinone and indanone groups are twisted, with their five-membered rings adopting a half-chair and an envelope conformation, respectively. The two benzene rings and the mean plane of the indolinone and indanone groups make dihedral angles of 71.98 (10), 84.32 (10), 86.26 (9) and 78.50 (9)°, respectively, with the central pyrrolidine ring. Intramolecular C—H⋯O hydrogen bonds stabilize the molecular conformation. In the crystal, pairs of intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. The dimers are interconnected into ribbons propagating along [110] via weak intermolecular C—H⋯O hydrogen bonds. Weak intermolecular C—H⋯π and π–π [centroid–centroid distance = 3.6509 (11) Å] interactions are also observed.

Related literature

For general background to heterocycles, see: Kirsch et al. (2004 ); Shi et al. (2009 ); Nair et al. (2007 ); Nájera et al. (2005 ); Coldham et al. (2005 ). For general background to pyrrolidine derivatives, see: Daly et al. (1986 ). For the biological activity of isatin derivatives and spiropyrrolidinyloxindoles, see: Cui et al. (1996 ); Xue et al. (2000 ); Klumpp et al. (1998 ); Hilton et al. (2000 ). For ring conformations, see Cremer & Pople (1975 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₃₃H₂₈N₂O₄
M_r = 516.57
Triclinic, $[P \overline 1]$
a = 9.2746 (12) Å
b = 10.6337 (15) Å
c = 14.4279 (19) Å
α = 92.369 (3)°
β = 98.557 (3)°
γ = 115.341 (2)°
V = 1262.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.28 × 0.19 × 0.07 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.976, T_max = 0.994
20001 measured reflections
7399 independent reflections
4778 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.159
S = 1.05
7399 reflections
360 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg3 and Cg4 are the centroids of the C26–C31, C20–C25 and C13–C18 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2ⁱ	0.94 (2)	1.94 (2)	2.8559 (19)	164 (2)
C8—H8B⋯O2	0.97	2.49	3.214 (2)	131
C11—H11A⋯O2	0.98	2.55	3.148 (2)	119
C22—H22A⋯O4ⁱⁱ	0.93	2.59	3.471 (2)	159
N1—H1N1⋯Cg2ⁱⁱⁱ	0.93 (2)	2.55 (2)	3.4518 (17)	161.7 (16)
C17—H17A⋯Cg3^iv	0.93	2.81	3.5609 (18)	139
C28—H28A⋯Cg4ⁱⁱⁱ	0.93	2.92	3.501 (2)	121
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x+1, y+1, z; (iii) -x+1, -y+1, -z+1; (iv) x-1, y-1, z.

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035865/rz2484sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035865/rz2484Isup2.hkl

checkCIF report

Comment top

The development of new efficient methods to synthesize nitrogen heterocycles with structural diversity is one of the major objectives of modern synthetic organic chemists (Kirsch et al., 2004). Multicomponent 1,3-dipolar cycloaddition of ylidic species, such as azomethine ylides with olefinic dipolarophiles, plays a key role in the construction of biologically active five-membered heterocycles (Shi et al., 2009; Nair et al., 2007; Nájera et al., 2005; Coldham et al., 2005). Highly substituted pyrrolidines have gained much prominence since they form the central skeleton of many natural products (Daly et al., 1986). Isatin and its derivatives possess interesting biological activities and are widely used as precursors for many natural products (Cui et al., 1996, Xue et al., 2000, Klumpp et al., 1998). Spiropyrrolidinyloxindoles are also found in a number of alkaloids of biological importance (Hilton et al., 2000). Due to the biological importance of the aforesaid heterocycles, the crystal structure determination of the title compound was carried out and the results are presented in this paper.

The molecular structure of the title compound is shown in Fig. 1. The central pyrrolidine ring (N1/C12/C9–C11) adopts a half-chair conformation (twisted on the N1–C11 bond), with puckering parameters Q = 0.4196 (18) Å and ϕ = 198.1 (2)° (Cremer & Pople, 1975). Both indolinone and indanone groups are twisted with their five-membered rings adopting a half chair (twisted on the C12–C19 bond) and an envelope (flap on the C9 atom) conformation respectively. The puckering parameters of these two rings are Q = 0.1316 (18) Å, ϕ = 127.6 (8)° and Q = 0.2814 (19) Å, ϕ = 323.9 (4)°. The two benzene rings (C20–C25 and C26–C31) and the mean plane of indolinone and indanone groups make dihedral angles of 71.98 (10), 84.32 (10), 86.26 (9) and 78.50 (9)°, respectively, with the central pyrrolidine ring. Intramolecular C8—H8B···O2 and C11—H11A···O2 hydrogen bonds (Table 1) stabilize the molecular structure. In the crystal structure, intermolecular N2—H1N2···O2 hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2). These dimers are interconnected into ribbons propagating along the [110] direction via weak intermolecular C22—H22A···O4 hydrogen bonds (Fig. 2, Table 1). Weak intermolecular C—H···π (Table 1) and π–π interactions are also observed (Cg1···Cg1^v = 3.6509 (11) Å; (v) = 1-x, -y, -z. Cg1 is centroid of benzene ring C2–C7).

Related literature top

For general background to heterocycles, see: Kirsch et al. (2004); Shi et al. (2009); Nair et al. (2007); Nájera et al. (2005); Coldham et al. (2005). For general background to pyrrolidine derivatives, see: Daly et al. (1986). For the biological activity of isatin derivatives and spiropyrrolidinyloxindoles, see: Cui et al. (1996); Xue et al. (2000); Klumpp et al. (1998); Hilton et al. (2000). For ring conformations, see Cremer & Pople (1975). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of (E)-2-bezylylidene-5,6-dimethoxy-2,3-dihydro-1H-indene-1-one (0.001 mmol), isatin (0.001 mmol) and phenylglycine (0.002 mmol) was dissolved in methanol (10 ml) and refluxed for 4 h. After completion of the reaction as evident from TLC, the mixture was poured into water (50 ml). The precipitated solid was filtered, washed with water and recrystallized from a petroleum ether-ethyl acetate mixture (1:1 v/v) to give the title compound as yellow crystals.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels and 50% probability ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of title compound, showing chains along the [110] direction. Intermolecular hydrogen bonds are shown as dashed lines.

5,6-Dimethoxy-4',5'-diphenylindane-2-spiro-3'-pyrrolidine-2'-spiro-3''- indoline-1,2''-dione top

Crystal data top

C₃₃H₂₈N₂O₄	Z = 2
M_r = 516.57	F(000) = 544
Triclinic, P1	D_x = 1.358 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2746 (12) Å	Cell parameters from 2918 reflections
b = 10.6337 (15) Å	θ = 2.4–29.7°
c = 14.4279 (19) Å	µ = 0.09 mm⁻¹
α = 92.369 (3)°	T = 100 K
β = 98.557 (3)°	Plate, yellow
γ = 115.341 (2)°	0.28 × 0.19 × 0.07 mm
V = 1262.9 (3) Å³

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	7399 independent reflections
Radiation source: fine-focus sealed tube	4778 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ϕ and ω scans	θ_max = 30.2°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
T_min = 0.976, T_max = 0.994	k = −15→15
20001 measured reflections	l = −20→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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0759P)² + 0.0467P] where P = (F_o² + 2F_c²)/3
7399 reflections	(Δ/σ)_max < 0.001
360 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₃₃H₂₈N₂O₄	γ = 115.341 (2)°
M_r = 516.57	V = 1262.9 (3) Å³
Triclinic, P1	Z = 2
a = 9.2746 (12) Å	Mo Kα radiation
b = 10.6337 (15) Å	µ = 0.09 mm⁻¹
c = 14.4279 (19) Å	T = 100 K
α = 92.369 (3)°	0.28 × 0.19 × 0.07 mm
β = 98.557 (3)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	7399 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4778 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.994	R_int = 0.054
20001 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.41 e Å⁻³
7399 reflections	Δρ_min = −0.32 e Å⁻³
360 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.38580 (14)	0.30325 (11)	0.12688 (8)	0.0175 (3)
O2	0.63136 (15)	0.17078 (11)	0.45955 (9)	0.0190 (3)
O3	0.36325 (15)	−0.30867 (11)	0.04324 (9)	0.0220 (3)
O4	0.13257 (16)	−0.24781 (12)	−0.02810 (9)	0.0235 (3)
N1	0.47665 (17)	0.35081 (13)	0.37988 (10)	0.0135 (3)
N2	0.38428 (18)	−0.00712 (13)	0.38690 (10)	0.0164 (3)
C1	0.4391 (2)	0.22526 (15)	0.16088 (12)	0.0138 (3)
C2	0.4020 (2)	0.08196 (15)	0.12244 (12)	0.0147 (3)
C3	0.2695 (2)	−0.01163 (16)	0.05522 (12)	0.0172 (4)
H3A	0.1907	0.0138	0.0268	0.021*
C4	0.2594 (2)	−0.14310 (16)	0.03240 (12)	0.0178 (4)
C5	0.3844 (2)	−0.17795 (16)	0.07342 (12)	0.0170 (4)
C6	0.5147 (2)	−0.08336 (16)	0.14044 (12)	0.0172 (4)
H6A	0.5966	−0.1062	0.1672	0.021*
C7	0.5197 (2)	0.04618 (15)	0.16652 (12)	0.0142 (3)
C8	0.6448 (2)	0.16427 (15)	0.23820 (12)	0.0150 (3)
H8A	0.7433	0.2149	0.2136	0.018*
H8B	0.6715	0.1293	0.2961	0.018*
C9	0.5599 (2)	0.25859 (15)	0.25492 (11)	0.0133 (3)
C10	0.66796 (19)	0.41814 (14)	0.28257 (11)	0.0129 (3)
H10A	0.6179	0.4660	0.2422	0.016*
C11	0.6481 (2)	0.44920 (15)	0.38374 (12)	0.0136 (3)
H11A	0.7192	0.4258	0.4297	0.016*
C12	0.44986 (19)	0.21556 (15)	0.33531 (11)	0.0128 (3)
C13	0.2716 (2)	0.11722 (15)	0.30263 (11)	0.0134 (3)
C14	0.1448 (2)	0.14017 (17)	0.25703 (13)	0.0177 (4)
H14A	0.1620	0.2282	0.2401	0.021*
C15	−0.0105 (2)	0.02774 (18)	0.23695 (13)	0.0225 (4)
H15A	−0.0973	0.0411	0.2060	0.027*
C16	−0.0361 (2)	−0.10321 (18)	0.26268 (14)	0.0228 (4)
H16A	−0.1395	−0.1772	0.2469	0.027*
C17	0.0892 (2)	−0.12627 (16)	0.31155 (13)	0.0200 (4)
H17A	0.0716	−0.2137	0.3300	0.024*
C18	0.2417 (2)	−0.01366 (16)	0.33174 (12)	0.0152 (3)
C19	0.5038 (2)	0.12758 (15)	0.40229 (12)	0.0150 (3)
C20	0.8407 (2)	0.47122 (15)	0.26691 (12)	0.0144 (3)
C21	0.8771 (2)	0.51532 (16)	0.17995 (12)	0.0177 (4)
H21A	0.7952	0.5145	0.1337	0.021*
C22	1.0331 (2)	0.56052 (17)	0.16100 (13)	0.0215 (4)
H22A	1.0546	0.5885	0.1023	0.026*
C23	1.1560 (2)	0.56373 (19)	0.22949 (15)	0.0265 (4)
H23A	1.2609	0.5954	0.2174	0.032*
C24	1.1231 (2)	0.5198 (2)	0.31617 (15)	0.0302 (5)
H24A	1.2057	0.5213	0.3621	0.036*
C25	0.9666 (2)	0.47344 (19)	0.33457 (14)	0.0230 (4)
H25A	0.9454	0.4434	0.3928	0.028*
C26	0.6764 (2)	0.59922 (15)	0.40689 (12)	0.0141 (3)
C27	0.8097 (2)	0.69237 (16)	0.47249 (12)	0.0175 (4)
H27A	0.8812	0.6619	0.5047	0.021*
C28	0.8366 (2)	0.83123 (16)	0.49029 (13)	0.0199 (4)
H28A	0.9251	0.8926	0.5350	0.024*
C29	0.7325 (2)	0.87811 (16)	0.44184 (13)	0.0209 (4)
H29A	0.7525	0.9715	0.4526	0.025*
C30	0.5976 (2)	0.78502 (17)	0.37694 (13)	0.0202 (4)
H30A	0.5261	0.8157	0.3450	0.024*
C31	0.5697 (2)	0.64619 (16)	0.35990 (12)	0.0166 (4)
H31A	0.4791	0.5841	0.3168	0.020*
C32	0.4881 (2)	−0.34828 (18)	0.07941 (14)	0.0247 (4)
H32A	0.4591	−0.4421	0.0529	0.037*
H32B	0.5002	−0.3441	0.1469	0.037*
H32C	0.5886	−0.2853	0.0627	0.037*
C33	−0.0201 (2)	−0.24280 (19)	−0.03764 (15)	0.0283 (5)
H33A	−0.0999	−0.3202	−0.0815	0.042*
H33B	−0.0102	−0.1565	−0.0605	0.042*
H33C	−0.0531	−0.2484	0.0226	0.042*
H1N1	0.444 (2)	0.3484 (19)	0.4383 (14)	0.017 (5)*
H1N2	0.380 (3)	−0.073 (2)	0.4293 (18)	0.047 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0181 (7)	0.0174 (5)	0.0193 (6)	0.0094 (5)	0.0047 (5)	0.0057 (4)
O2	0.0173 (7)	0.0188 (5)	0.0199 (6)	0.0072 (5)	0.0021 (5)	0.0052 (5)
O3	0.0247 (7)	0.0154 (5)	0.0263 (7)	0.0094 (5)	0.0056 (6)	−0.0030 (5)
O4	0.0218 (7)	0.0198 (6)	0.0229 (7)	0.0061 (5)	−0.0019 (6)	−0.0054 (5)
N1	0.0127 (7)	0.0118 (5)	0.0167 (7)	0.0046 (5)	0.0074 (6)	0.0016 (5)
N2	0.0179 (8)	0.0131 (6)	0.0185 (7)	0.0065 (5)	0.0047 (6)	0.0041 (5)
C1	0.0124 (8)	0.0148 (6)	0.0152 (8)	0.0056 (6)	0.0059 (7)	0.0043 (6)
C2	0.0169 (9)	0.0130 (6)	0.0143 (8)	0.0057 (6)	0.0057 (7)	0.0028 (6)
C3	0.0189 (9)	0.0161 (7)	0.0157 (8)	0.0067 (6)	0.0039 (7)	0.0023 (6)
C4	0.0182 (9)	0.0163 (7)	0.0141 (8)	0.0033 (6)	0.0027 (7)	−0.0005 (6)
C5	0.0205 (9)	0.0140 (7)	0.0171 (8)	0.0070 (6)	0.0079 (7)	0.0009 (6)
C6	0.0170 (9)	0.0157 (7)	0.0198 (9)	0.0071 (6)	0.0059 (7)	0.0016 (6)
C7	0.0149 (9)	0.0141 (6)	0.0146 (8)	0.0056 (6)	0.0075 (7)	0.0027 (6)
C8	0.0124 (8)	0.0140 (6)	0.0192 (8)	0.0057 (6)	0.0049 (7)	0.0023 (6)
C9	0.0133 (8)	0.0115 (6)	0.0145 (8)	0.0047 (6)	0.0027 (7)	0.0022 (5)
C10	0.0118 (8)	0.0111 (6)	0.0153 (8)	0.0043 (6)	0.0029 (7)	0.0022 (5)
C11	0.0116 (8)	0.0121 (6)	0.0159 (8)	0.0044 (6)	0.0019 (7)	0.0018 (5)
C12	0.0118 (8)	0.0118 (6)	0.0152 (8)	0.0050 (6)	0.0043 (7)	0.0023 (5)
C13	0.0123 (8)	0.0130 (6)	0.0138 (8)	0.0041 (6)	0.0046 (7)	0.0011 (5)
C14	0.0136 (9)	0.0182 (7)	0.0217 (9)	0.0063 (6)	0.0066 (7)	0.0027 (6)
C15	0.0159 (10)	0.0246 (8)	0.0242 (10)	0.0069 (7)	0.0023 (8)	0.0014 (7)
C16	0.0130 (9)	0.0215 (8)	0.0271 (10)	0.0012 (6)	0.0052 (8)	−0.0016 (7)
C17	0.0215 (10)	0.0133 (7)	0.0222 (9)	0.0034 (6)	0.0087 (8)	0.0011 (6)
C18	0.0151 (9)	0.0155 (7)	0.0158 (8)	0.0067 (6)	0.0058 (7)	0.0014 (6)
C19	0.0170 (9)	0.0133 (6)	0.0168 (8)	0.0073 (6)	0.0065 (7)	0.0034 (6)
C20	0.0131 (8)	0.0116 (6)	0.0182 (8)	0.0045 (6)	0.0050 (7)	0.0015 (6)
C21	0.0167 (9)	0.0184 (7)	0.0172 (8)	0.0070 (6)	0.0034 (7)	0.0030 (6)
C22	0.0200 (10)	0.0230 (8)	0.0214 (9)	0.0073 (7)	0.0093 (8)	0.0061 (7)
C23	0.0175 (10)	0.0316 (9)	0.0305 (11)	0.0087 (7)	0.0103 (9)	0.0082 (8)
C24	0.0156 (10)	0.0464 (11)	0.0295 (11)	0.0134 (8)	0.0048 (9)	0.0137 (9)
C25	0.0162 (10)	0.0321 (9)	0.0238 (10)	0.0113 (7)	0.0078 (8)	0.0125 (7)
C26	0.0142 (9)	0.0131 (6)	0.0159 (8)	0.0054 (6)	0.0071 (7)	0.0022 (6)
C27	0.0159 (9)	0.0161 (7)	0.0189 (8)	0.0051 (6)	0.0048 (7)	0.0028 (6)
C28	0.0191 (10)	0.0152 (7)	0.0204 (9)	0.0018 (6)	0.0075 (7)	0.0005 (6)
C29	0.0273 (10)	0.0137 (7)	0.0237 (9)	0.0075 (7)	0.0150 (8)	0.0031 (6)
C30	0.0236 (10)	0.0201 (7)	0.0230 (9)	0.0138 (7)	0.0082 (8)	0.0049 (6)
C31	0.0160 (9)	0.0150 (7)	0.0188 (8)	0.0064 (6)	0.0049 (7)	0.0010 (6)
C32	0.0298 (11)	0.0196 (8)	0.0299 (10)	0.0142 (7)	0.0101 (9)	0.0022 (7)
C33	0.0230 (11)	0.0236 (8)	0.0314 (11)	0.0083 (7)	−0.0082 (9)	−0.0013 (7)

Geometric parameters (Å, º) top

O1—C1	1.2189 (19)	C14—C15	1.400 (2)
O2—C19	1.227 (2)	C14—H14A	0.9300
O3—C5	1.3606 (18)	C15—C16	1.385 (3)
O3—C32	1.430 (2)	C15—H15A	0.9300
O4—C4	1.3704 (19)	C16—C17	1.387 (3)
O4—C33	1.427 (2)	C16—H16A	0.9300
N1—C12	1.4540 (19)	C17—C18	1.385 (2)
N1—C11	1.473 (2)	C17—H17A	0.9300
N1—H1N1	0.93 (2)	C20—C21	1.395 (2)
N2—C19	1.3678 (19)	C20—C25	1.398 (2)
N2—C18	1.411 (2)	C21—C22	1.390 (3)
N2—H1N2	0.94 (3)	C21—H21A	0.9300
C1—C2	1.474 (2)	C22—C23	1.381 (3)
C1—C9	1.546 (2)	C22—H22A	0.9300
C2—C7	1.382 (2)	C23—C24	1.384 (3)
C2—C3	1.400 (2)	C23—H23A	0.9300
C3—C4	1.383 (2)	C24—C25	1.390 (3)
C3—H3A	0.9300	C24—H24A	0.9300
C4—C5	1.419 (3)	C25—H25A	0.9300
C5—C6	1.392 (2)	C26—C27	1.390 (2)
C6—C7	1.392 (2)	C26—C31	1.393 (2)
C6—H6A	0.9300	C27—C28	1.394 (2)
C7—C8	1.510 (2)	C27—H27A	0.9300
C8—C9	1.548 (2)	C28—C29	1.382 (3)
C8—H8A	0.9700	C28—H28A	0.9300
C8—H8B	0.9700	C29—C30	1.392 (2)
C9—C10	1.5529 (19)	C29—H29A	0.9300
C9—C12	1.610 (2)	C30—C31	1.390 (2)
C10—C20	1.510 (2)	C30—H30A	0.9300
C10—C11	1.538 (2)	C31—H31A	0.9300
C10—H10A	0.9800	C32—H32A	0.9600
C11—C26	1.515 (2)	C32—H32B	0.9600
C11—H11A	0.9800	C32—H32C	0.9600
C12—C13	1.515 (2)	C33—H33A	0.9600
C12—C19	1.546 (2)	C33—H33B	0.9600
C13—C14	1.380 (2)	C33—H33C	0.9600
C13—C18	1.394 (2)

C5—O3—C32	117.45 (13)	C15—C14—H14A	120.8
C4—O4—C33	116.29 (14)	C16—C15—C14	120.72 (18)
C12—N1—C11	107.96 (13)	C16—C15—H15A	119.6
C12—N1—H1N1	114.7 (11)	C14—C15—H15A	119.6
C11—N1—H1N1	113.2 (11)	C15—C16—C17	121.36 (16)
C19—N2—C18	110.48 (13)	C15—C16—H16A	119.3
C19—N2—H1N2	122.2 (14)	C17—C16—H16A	119.3
C18—N2—H1N2	121.4 (14)	C18—C17—C16	117.18 (15)
O1—C1—C2	127.74 (15)	C18—C17—H17A	121.4
O1—C1—C9	125.95 (14)	C16—C17—H17A	121.4
C2—C1—C9	106.31 (13)	C17—C18—C13	122.37 (16)
C7—C2—C3	122.17 (14)	C17—C18—N2	127.89 (15)
C7—C2—C1	108.94 (14)	C13—C18—N2	109.63 (14)
C3—C2—C1	128.85 (16)	O2—C19—N2	125.76 (15)
C4—C3—C2	117.96 (16)	O2—C19—C12	126.09 (14)
C4—C3—H3A	121.0	N2—C19—C12	108.15 (14)
C2—C3—H3A	121.0	C21—C20—C25	117.69 (16)
O4—C4—C3	124.41 (16)	C21—C20—C10	119.25 (15)
O4—C4—C5	115.38 (14)	C25—C20—C10	123.00 (16)
C3—C4—C5	120.21 (15)	C22—C21—C20	121.40 (17)
O3—C5—C6	124.50 (16)	C22—C21—H21A	119.3
O3—C5—C4	114.75 (14)	C20—C21—H21A	119.3
C6—C5—C4	120.74 (14)	C23—C22—C21	119.83 (18)
C5—C6—C7	118.61 (16)	C23—C22—H22A	120.1
C5—C6—H6A	120.7	C21—C22—H22A	120.1
C7—C6—H6A	120.7	C22—C23—C24	119.96 (19)
C2—C7—C6	120.14 (15)	C22—C23—H23A	120.0
C2—C7—C8	111.20 (13)	C24—C23—H23A	120.0
C6—C7—C8	128.63 (16)	C23—C24—C25	120.06 (19)
C7—C8—C9	103.46 (13)	C23—C24—H24A	120.0
C7—C8—H8A	111.1	C25—C24—H24A	120.0
C9—C8—H8A	111.1	C24—C25—C20	121.04 (18)
C7—C8—H8B	111.1	C24—C25—H25A	119.5
C9—C8—H8B	111.1	C20—C25—H25A	119.5
H8A—C8—H8B	109.0	C27—C26—C31	119.13 (14)
C1—C9—C8	102.10 (13)	C27—C26—C11	121.23 (15)
C1—C9—C10	112.78 (12)	C31—C26—C11	119.62 (14)
C8—C9—C10	117.99 (14)	C26—C27—C28	120.29 (17)
C1—C9—C12	105.46 (13)	C26—C27—H27A	119.9
C8—C9—C12	114.60 (12)	C28—C27—H27A	119.9
C10—C9—C12	103.53 (12)	C29—C28—C27	120.33 (16)
C20—C10—C11	115.67 (13)	C29—C28—H28A	119.8
C20—C10—C9	115.57 (13)	C27—C28—H28A	119.8
C11—C10—C9	105.43 (12)	C28—C29—C30	119.71 (15)
C20—C10—H10A	106.5	C28—C29—H29A	120.1
C11—C10—H10A	106.5	C30—C29—H29A	120.1
C9—C10—H10A	106.5	C31—C30—C29	119.96 (17)
N1—C11—C26	111.09 (14)	C31—C30—H30A	120.0
N1—C11—C10	100.59 (12)	C29—C30—H30A	120.0
C26—C11—C10	112.87 (13)	C30—C31—C26	120.55 (16)
N1—C11—H11A	110.6	C30—C31—H31A	119.7
C26—C11—H11A	110.6	C26—C31—H31A	119.7
C10—C11—H11A	110.6	O3—C32—H32A	109.5
N1—C12—C13	112.92 (14)	O3—C32—H32B	109.5
N1—C12—C19	114.28 (13)	H32A—C32—H32B	109.5
C13—C12—C19	100.96 (12)	O3—C32—H32C	109.5
N1—C12—C9	102.56 (12)	H32A—C32—H32C	109.5
C13—C12—C9	116.62 (13)	H32B—C32—H32C	109.5
C19—C12—C9	110.00 (13)	O4—C33—H33A	109.5
C14—C13—C18	119.81 (15)	O4—C33—H33B	109.5
C14—C13—C12	131.21 (14)	H33A—C33—H33B	109.5
C18—C13—C12	108.86 (14)	O4—C33—H33C	109.5
C13—C14—C15	118.43 (15)	H33A—C33—H33C	109.5
C13—C14—H14A	120.8	H33B—C33—H33C	109.5

O1—C1—C2—C7	162.86 (17)	C10—C9—C12—C13	137.35 (14)
C9—C1—C2—C7	−17.63 (18)	C1—C9—C12—C19	132.81 (13)
O1—C1—C2—C3	−19.4 (3)	C8—C9—C12—C19	21.35 (17)
C9—C1—C2—C3	160.08 (17)	C10—C9—C12—C19	−108.52 (13)
C7—C2—C3—C4	−0.8 (3)	N1—C12—C13—C14	42.9 (2)
C1—C2—C3—C4	−178.21 (17)	C19—C12—C13—C14	165.38 (18)
C33—O4—C4—C3	−25.8 (3)	C9—C12—C13—C14	−75.5 (2)
C33—O4—C4—C5	153.32 (16)	N1—C12—C13—C18	−132.94 (15)
C2—C3—C4—O4	176.31 (16)	C19—C12—C13—C18	−10.49 (17)
C2—C3—C4—C5	−2.8 (3)	C9—C12—C13—C18	108.63 (16)
C32—O3—C5—C6	−3.4 (3)	C18—C13—C14—C15	−3.3 (3)
C32—O3—C5—C4	177.80 (15)	C12—C13—C14—C15	−178.79 (17)
O4—C4—C5—O3	2.8 (2)	C13—C14—C15—C16	0.3 (3)
C3—C4—C5—O3	−178.02 (16)	C14—C15—C16—C17	2.1 (3)
O4—C4—C5—C6	−176.01 (16)	C15—C16—C17—C18	−1.3 (3)
C3—C4—C5—C6	3.2 (3)	C16—C17—C18—C13	−1.8 (3)
O3—C5—C6—C7	−178.60 (16)	C16—C17—C18—N2	174.15 (17)
C4—C5—C6—C7	0.1 (3)	C14—C13—C18—C17	4.1 (3)
C3—C2—C7—C6	4.0 (3)	C12—C13—C18—C17	−179.45 (16)
C1—C2—C7—C6	−178.06 (15)	C14—C13—C18—N2	−172.44 (16)
C3—C2—C7—C8	−177.88 (16)	C12—C13—C18—N2	3.98 (19)
C1—C2—C7—C8	0.0 (2)	C19—N2—C18—C17	−170.80 (18)
C5—C6—C7—C2	−3.6 (3)	C19—N2—C18—C13	5.5 (2)
C5—C6—C7—C8	178.69 (16)	C18—N2—C19—O2	167.44 (17)
C2—C7—C8—C9	17.35 (18)	C18—N2—C19—C12	−12.43 (19)
C6—C7—C8—C9	−164.79 (17)	N1—C12—C19—O2	−44.6 (2)
O1—C1—C9—C8	−153.34 (17)	C13—C12—C19—O2	−166.11 (17)
C2—C1—C9—C8	27.14 (16)	C9—C12—C19—O2	70.1 (2)
O1—C1—C9—C10	−25.7 (2)	N1—C12—C19—N2	135.26 (15)
C2—C1—C9—C10	154.77 (14)	C13—C12—C19—N2	13.76 (17)
O1—C1—C9—C12	86.59 (19)	C9—C12—C19—N2	−110.03 (15)
C2—C1—C9—C12	−92.93 (14)	C11—C10—C20—C21	−146.90 (14)
C7—C8—C9—C1	−26.21 (15)	C9—C10—C20—C21	89.24 (18)
C7—C8—C9—C10	−150.44 (14)	C11—C10—C20—C25	35.7 (2)
C7—C8—C9—C12	87.24 (15)	C9—C10—C20—C25	−88.16 (19)
C1—C9—C10—C20	−104.01 (17)	C25—C20—C21—C22	−0.2 (2)
C8—C9—C10—C20	14.7 (2)	C10—C20—C21—C22	−177.77 (14)
C12—C9—C10—C20	142.51 (14)	C20—C21—C22—C23	−0.7 (3)
C1—C9—C10—C11	126.92 (15)	C21—C22—C23—C24	1.1 (3)
C8—C9—C10—C11	−114.35 (16)	C22—C23—C24—C25	−0.5 (3)
C12—C9—C10—C11	13.44 (16)	C23—C24—C25—C20	−0.5 (3)
C12—N1—C11—C26	166.16 (13)	C21—C20—C25—C24	0.8 (3)
C12—N1—C11—C10	46.44 (15)	C10—C20—C25—C24	178.29 (16)
C20—C10—C11—N1	−164.04 (12)	N1—C11—C26—C27	135.61 (16)
C9—C10—C11—N1	−35.03 (15)	C10—C11—C26—C27	−112.28 (18)
C20—C10—C11—C26	77.52 (17)	N1—C11—C26—C31	−46.1 (2)
C9—C10—C11—C26	−153.47 (14)	C10—C11—C26—C31	66.0 (2)
C11—N1—C12—C13	−164.04 (13)	C31—C26—C27—C28	−0.5 (3)
C11—N1—C12—C19	81.30 (17)	C11—C26—C27—C28	177.73 (16)
C11—N1—C12—C9	−37.70 (16)	C26—C27—C28—C29	−1.0 (3)
C1—C9—C12—N1	−105.23 (13)	C27—C28—C29—C30	1.8 (3)
C8—C9—C12—N1	143.31 (13)	C28—C29—C30—C31	−1.1 (3)
C10—C9—C12—N1	13.44 (15)	C29—C30—C31—C26	−0.4 (3)
C1—C9—C12—C13	18.68 (17)	C27—C26—C31—C30	1.2 (3)
C8—C9—C12—C13	−92.78 (17)	C11—C26—C31—C30	−177.07 (16)

Hydrogen-bond geometry (Å, º) top

Cg2, Cg3 and Cg4 are the centroids of the C26–C31, C20–C25 and C13–C18 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2ⁱ	0.94 (2)	1.94 (2)	2.8559 (19)	164 (2)
C8—H8B···O2	0.97	2.49	3.214 (2)	131
C11—H11A···O2	0.98	2.55	3.148 (2)	119
C22—H22A···O4ⁱⁱ	0.93	2.59	3.471 (2)	159
N1—H1N1···Cg2ⁱⁱⁱ	0.93 (2)	2.55 (2)	3.4518 (17)	161.7 (16)
C17—H17A···Cg3^iv	0.93	2.81	3.5609 (18)	139
C28—H28A···Cg4ⁱⁱⁱ	0.93	2.92	3.501 (2)	121

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

Experimental details

Crystal data
Chemical formula	C₃₃H₂₈N₂O₄
M_r	516.57
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.2746 (12), 10.6337 (15), 14.4279 (19)
α, β, γ (°)	92.369 (3), 98.557 (3), 115.341 (2)
V (Å³)	1262.9 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.19 × 0.07

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.976, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	20001, 7399, 4778
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.708

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.159, 1.05
No. of reflections	7399
No. of parameters	360
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.32

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2, Cg3 and Cg4 are the centroids of the C26–C31, C20–C25 and C13–C18 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2ⁱ	0.94 (2)	1.94 (2)	2.8559 (19)	164 (2)
C8—H8B···O2	0.97	2.49	3.214 (2)	131
C11—H11A···O2	0.98	2.55	3.148 (2)	119
C22—H22A···O4ⁱⁱ	0.93	2.59	3.471 (2)	159
N1—H1N1···Cg2ⁱⁱⁱ	0.93 (2)	2.55 (2)	3.4518 (17)	161.7 (16)
C17—H17A···Cg3^iv	0.93	2.81	3.5609 (18)	139
C28—H28A···Cg4ⁱⁱⁱ	0.93	2.92	3.501 (2)	121

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

Footnotes

‡Thomson Reuters ResearcherID: A-5523-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors wish to express their thanks to Universiti of Sains Malysia (USM) for providing research facilities. HKF thanks USM for the Research University Grant No. 1001/PFIZIK/811160 and CSY thanks USM for the award of a USM Fellowship.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Coldham, I. & Hufton, R. (2005). Chem. Rev. 105, 2765–2810. Web of Science CrossRef PubMed CAS Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Cui, C.-B., Kakeya, H. & Osada, H. (1996). Tetrahedron, 52, 12651–12666. CrossRef CAS Web of Science Google Scholar
Daly, J. W., Spande, T. W., Whittaker, N., Highet, R. J., Feigl, D., Noshimori, N., Tokuyama, T. & Meyers, C. W. (1986). J. Nat. Prod. 49, 265–280. CrossRef CAS PubMed Web of Science Google Scholar
Hilton, S. T., Ho, T. C. T., Pljevaljcic, G. & Jones, K. (2000). Org. Lett. 2, 2639–2641. Web of Science CrossRef PubMed CAS Google Scholar
Kirsch, G., Hesse, S. & Comel, A. (2004). Curr. Org. Chem. 1, 47–63. CAS Google Scholar
Klumpp, D. A., Yeung, K. Y., Prakash, G. K. S. & Olah, G. A. (1998). J. Org. Chem. 63, 4481–4484. Web of Science CrossRef CAS Google Scholar
Nair, V. & Suja, T. D. (2007). Tetrahedron, 63, 12247–12275. Web of Science CrossRef CAS Google Scholar
Nájera, C. N. & Sansano, J. M. (2005). Angew. Chem. 117, 6428–6432. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, F., Mancuso, R. & Larock, R. C. (2009). Tetrahedron Lett. 50, 4067–4070. Web of Science CrossRef CAS PubMed Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xue, J., Zhang, Y., Wang, X.-I., Fun, H. K. & Xu, J.-H. (2000). Org. Lett. 2, 2583–2586. Web of Science CSD CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2533-o2534

doi:10.1107/S1600536810035865

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

5,6-Dimeth­­oxy-4′,5′-di­phenyl­indane-2-spiro-3′-pyrrolidine-2′-spiro-3′′-indoline-1,2′′-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

5,6-Dimethoxy-4′,5′-diphenylindane-2-spiro-3′-pyrrolidine-2′-spiro-3′′-indoline-1,2′′-dione