Ethyl 1'-[1-(4-methoxyphenyl)-3-phenoxy-4-phenylazetidin-1-yl]-1,3-dioxo-2′,3′,5′,6′,7′,7a′-hexahydroindan-2-spiro-3′-1′H-pyrrolizine-2′-carboxylate

Kamala, E.T.S.; Nirmala, S.; Sudha, L.; Arumugam, N.; Raghunathan, R.

doi:10.1107/S1600536808026913

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages o1832-o1833

doi:10.1107/S1600536808026913

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Ethyl 1'-[1-(4-methoxyphenyl)-3-phenoxy-4-phenylazetidin-1-yl]-1,3-dioxo-2′,3′,5′,6′,7′,7a′-hexahydroindan-2-spiro-3′-1′H-pyrrolizine-2′-carboxylate

E. Theboral Sugi Kamala,^a S. Nirmala,^a L. Sudha,^b ^* N. Arumugam ^c and R. Raghunathan ^c

^aDepartment of Physics, Easwari Engineering College, Ramapuram, Chennai 600 089, India, ^bDepartment of Physics, SRM University, Ramapuram Campus, Chennai 600 089, India, and ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India.
^*Correspondence e-mail: sudharose18@gmail.com

(Received 17 August 2008; accepted 20 August 2008; online 30 August 2008)

In the title compound, C₃₄H₃₂N₂O₇, the methyl group and methylene H atoms of the ethoxycarbonyl substituent are disordered over two positions with site occupancy factors for the major and minor conformers of 0.594 (8) and 0.406 (8), respectively. The unsubstituted ring of the pyrrolizine ring system exhibits a twist conformation, the other an envelope conformation. In the crystal structure, molecules are linked through C—H⋯O hydrogen bonds; intramolecular C—H⋯O interactions are also observed.

Related literature

For related literature, see: Allen et al. (1987 ); Alonso et al. (2002 ); Aoyama et al. (2001 ); Chande et al. (2005 ); Cremer & Pople (1975 ); Escolano & Jones (2000 ); Halve et al. (2007 ); Kamala et al. (2008 ); Nardelli (1983 ); Pinna et al. (2002 ); Poornachandran & Raghunathan (2006 ); Raj & Raghunathan (2001 ); Raj et al. (2003 ).

Experimental

Crystal data

C₃₄H₃₂N₂O₇
M_r = 580.62
Monoclinic, P 2₁ /n
a = 12.4776 (7) Å
b = 12.4946 (6) Å
c = 19.4958 (11) Å
β = 106.013 (3)°
V = 2921.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.973, T_max = 0.982
66713 measured reflections
7446 independent reflections
4654 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.225
S = 0.92
7446 reflections
395 parameters
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O6ⁱ	0.98	2.45	3.151 (3)	129
C26—H26⋯O1ⁱⁱ	0.93	2.50	3.390 (4)	160
C8—H8A⋯O6	0.97	2.50	3.166 (4)	126
C10—H10⋯O2	0.98	2.24	2.987 (3)	132
C29—H29⋯O1	0.93	2.40	3.024 (3)	125
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026913/bt2772sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026913/bt2772Isup2.hkl

checkCIF report

Comment top

Pyrrolidine derivatives are widely used as organic catalysts and also serve as important structural units in biologically active molecules. Pyrrolidine derivatives, apart from displaying important biological activities (Pinna et al., 2002; Escolano & Jones, 2000), are present in natural products such as cephalotoxin, kainic acid, domoic acid and quinocarcin. The cycloaddition of azomethine ylides to dipolarophiles with exocyclic double bonds affords spiro-pyrrolidines (Raj & Raghunathan, 2001; Poornachandran & Raghunathan, 2006), which display important biological activities (Raj et al., 2003). In view of their very good antimycobacterial activity,synthesis of spiro compounds has drawn considerable attention from chemists (Chande et al., 2005). The azetidinone ring system is the common structural feature of a number of broad spectrum β-lactam antibiotics (Halve et al., 2007) and also possesses other pharmalogical properties (Aoyama et al., 2001). They are precursors of α,α-disubstituted β-amino acids (Alonso et al.,2002).

Fig. 1 shows the ORTEP (Farrugia, 1997) plot of compound (I). Bond lengths and angles are comparable with other reported values (Allen et al.,1987; Kamala et al.,2008). The atom C21 is disordered.

In the molecule the five membered rings N2/C5/C4/C10/C9 and C9/C11/C12/C17/C18 exhibit envelope conformation with envelopes on C10 and C9 respectively with the assymetry parameters (Nardelli,1983) ΔC_s(C10)/C(9) = 2.3 (2)/1.2 (2) and with the puckering parameters (Cremer and Pople,1975) q2 = 0.368 (2) Å/ 0.113 (2)Å and ϕ2 =104.4 (3)° / 184.2 (12)°. The pyrrolidine ring N2/C5—C8 exhibits twist conformation with assymetry parameter ΔC₂ (N2) =3.1 (3), and with the puckering parameters q2 = 0.365 (3) Å, ϕ2 = 272.4 (4)°.

The sum of bond angles around N1 [354.96°] and that around atom N2 [343.25°] indicate sp² hybridizations. The azetidinone ring is almost perpendicular to the pyrrolidine ring N2/C4/C5/C9/C10 making a dihedral angle of 88.70 (8)°. The other pyrrolidine ring N2/C5—C8 makes a dihedral angle of 80.15 (6)° with the central β lactam moiety while that of the phenyl ring is 60.19 (9)°.

In the crystal packing, atoms O1 and O6 are involved in intermolecular C - H···O interactions and atoms O1 and O2 are involved in intramolecular C - H···O interactions.

Related literature top

For related literature, see: Allen et al. (1987); Alonso et al. (2002); Aoyama et al. (2001); Chande et al. (2005); Cremer & Pople (1975); Escolano & Jones (2000); Halve et al. (2007); Kamala et al. (2008); Nardelli (1983); Pinna et al. (2002); Poornachandran & Raghunathan (2006); Raj & Raghunathan (2001); Raj et al. (2003).

Experimental top

To a solution of ninhydrin (1 mmol), proline (1 mmol) in dry acetonitrile (10 ml) was added β-azetidinyl crotonic ester (1 mmol) under nitrogen atmosphere. The solution was refluxed for 2–3 h. After completion of reaction the solvent was distilled off under reduced pressure. The crude product was purified by column chromatography using hexane: ethylacetate (8:2) as eluent. The product was crystallized by ethylacetate.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids.
	Fig. 2. The packing of the molecules viewed along b axis.

Ethyl 1'-[1-(4-methoxyphenyl)-3-phenoxy-4-phenylazetidin-1-yl]-1,3-dioxo- 2',3',5',6',7',7a'-hexahydroindan-2-spiro-3'-1'H-pyrrolizine-2'-carboxylate top

Crystal data top

C₃₄H₃₂N₂O₇	F(000) = 1224
M_r = 580.62	D_x = 1.320 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 66713 reflections
a = 12.4776 (7) Å	θ = 2.0–28.7°
b = 12.4946 (6) Å	µ = 0.09 mm⁻¹
c = 19.4958 (11) Å	T = 293 K
β = 106.013 (3)°	Prism, colourless
V = 2921.5 (3) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	7446 independent reflections
Radiation source: fine-focus sealed tube	4654 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω and ϕ scan	θ_max = 28.7°, θ_min = 2.0°
Absorption correction: multi-scan (Blessing, 1995)	h = −16→16
T_min = 0.973, T_max = 0.982	k = −16→16
66713 measured reflections	l = −26→26

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.225	H-atom parameters constrained
S = 0.92	w = 1/[σ²(F_o²) + (0.1376P)² + 1.4238P] where P = (F_o² + 2F_c²)/3
7446 reflections	(Δ/σ)_max < 0.001
395 parameters	Δρ_max = 0.70 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₃₄H₃₂N₂O₇	V = 2921.5 (3) Å³
M_r = 580.62	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.4776 (7) Å	µ = 0.09 mm⁻¹
b = 12.4946 (6) Å	T = 293 K
c = 19.4958 (11) Å	0.30 × 0.20 × 0.20 mm
β = 106.013 (3)°

Data collection top

Bruker Kappa APEXII diffractometer	7446 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	4654 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.982	R_int = 0.037
66713 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.225	H-atom parameters constrained
S = 0.92	Δρ_max = 0.70 e Å⁻³
7446 reflections	Δρ_min = −0.25 e Å⁻³
395 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	Occ. (<1)
C1	0.10567 (17)	0.74081 (19)	0.12572 (12)	0.0482 (5)
C2	0.20897 (17)	0.67935 (17)	0.16633 (12)	0.0457 (5)
H2	0.1884	0.6121	0.1852	0.055*
C3	0.22628 (15)	0.76987 (17)	0.22302 (11)	0.0414 (4)
H3	0.2171	0.7419	0.2680	0.050*
C4	0.32801 (15)	0.84224 (16)	0.23708 (10)	0.0386 (4)
H4	0.3175	0.9013	0.2676	0.046*
C5	0.43512 (16)	0.78329 (19)	0.27532 (11)	0.0456 (5)
H5	0.4292	0.7084	0.2598	0.055*
C6	0.4746 (2)	0.7876 (3)	0.35635 (13)	0.0686 (8)
H6A	0.4487	0.7259	0.3775	0.082*
H6B	0.4493	0.8524	0.3745	0.082*
C7	0.6006 (3)	0.7866 (3)	0.37091 (16)	0.0828 (9)
H7A	0.6364	0.8171	0.4173	0.099*
H7B	0.6280	0.7143	0.3691	0.099*
C8	0.6216 (2)	0.8539 (3)	0.31244 (15)	0.0715 (8)
H8A	0.6283	0.9288	0.3259	0.086*
H8B	0.6893	0.8315	0.3013	0.086*
C9	0.48118 (15)	0.91979 (17)	0.20062 (11)	0.0413 (4)
C10	0.35503 (15)	0.88984 (16)	0.17155 (10)	0.0383 (4)
H10	0.3473	0.8337	0.1354	0.046*
C11	0.49581 (16)	1.03640 (19)	0.22699 (12)	0.0470 (5)
C12	0.53156 (17)	1.10040 (19)	0.17360 (12)	0.0493 (5)
C13	0.5449 (2)	1.2101 (2)	0.17030 (17)	0.0686 (7)
H13	0.5286	1.2553	0.2040	0.082*
C14	0.5828 (3)	1.2501 (3)	0.11582 (19)	0.0835 (9)
H14	0.5923	1.3235	0.1126	0.100*
C15	0.6071 (3)	1.1836 (3)	0.06565 (17)	0.0780 (9)
H15	0.6333	1.2131	0.0296	0.094*
C16	0.5934 (2)	1.0753 (2)	0.06794 (14)	0.0607 (6)
H16	0.6095	1.0307	0.0339	0.073*
C17	0.55463 (16)	1.03373 (19)	0.12275 (11)	0.0468 (5)
C18	0.53427 (16)	0.92134 (18)	0.13783 (11)	0.0443 (5)
C19	0.28198 (16)	0.98272 (18)	0.13906 (11)	0.0425 (4)
C20	0.1937 (3)	1.0703 (3)	0.03029 (16)	0.0873 (10)
H20A	0.1358	1.0866	0.0532	0.105*	0.594 (8)
H20B	0.1582	1.0475	−0.0182	0.105*	0.594 (8)
H20C	0.2032	1.1346	0.0593	0.105*	0.406 (8)
H20D	0.2132	1.0867	−0.0134	0.105*	0.406 (8)
C21A	0.2620 (3)	1.1658 (3)	0.02972 (16)	0.107 (3)	0.594 (8)
H21A	0.2156	1.2225	0.0044	0.161*	0.594 (8)
H21B	0.3185	1.1494	0.0065	0.161*	0.594 (8)
H21C	0.2966	1.1881	0.0779	0.161*	0.594 (8)
C21B	0.0759 (8)	1.0331 (10)	0.0133 (6)	0.122 (5)	0.406 (8)
H21D	0.0275	1.0881	−0.0123	0.184*	0.406 (8)
H21E	0.0571	1.0175	0.0568	0.184*	0.406 (8)
H21F	0.0672	0.9697	−0.0155	0.184*	0.406 (8)
C22	0.27365 (19)	0.58488 (18)	0.08017 (12)	0.0491 (5)
C23	0.3552 (2)	0.5747 (2)	0.04537 (14)	0.0640 (7)
H23	0.4182	0.6181	0.0576	0.077*
C24	0.3422 (3)	0.4997 (4)	−0.00750 (19)	0.0970 (12)
H24	0.3968	0.4920	−0.0314	0.116*
C25	0.2488 (4)	0.4355 (4)	−0.0256 (2)	0.1091 (14)
H25	0.2407	0.3848	−0.0616	0.131*
C26	0.1680 (3)	0.4462 (3)	0.00915 (19)	0.0888 (10)
H26	0.1052	0.4025	−0.0030	0.107*
C27	0.1798 (2)	0.5210 (2)	0.06166 (15)	0.0627 (6)
H27	0.1246	0.5290	0.0850	0.075*
C28	0.03902 (16)	0.87881 (18)	0.19790 (11)	0.0432 (5)
C29	−0.07248 (19)	0.8653 (2)	0.16113 (14)	0.0612 (7)
H29	−0.0927	0.8169	0.1235	0.073*
C30	−0.1525 (2)	0.9233 (3)	0.18030 (15)	0.0716 (8)
H30	−0.2271	0.9139	0.1557	0.086*
C31	−0.12380 (17)	0.9960 (2)	0.23592 (13)	0.0521 (5)
C32	−0.01383 (18)	1.0081 (2)	0.27267 (13)	0.0539 (6)
H32	0.0064	1.0560	0.3105	0.065*
C33	0.06725 (17)	0.9490 (2)	0.25347 (13)	0.0541 (6)
H33	0.1417	0.9573	0.2788	0.065*
C34	−0.1843 (2)	1.1296 (3)	0.30349 (17)	0.0733 (8)
H34A	−0.2519	1.1612	0.3083	0.110*
H34B	−0.1390	1.1839	0.2905	0.110*
H34C	−0.1442	1.0979	0.3480	0.110*
N1	0.11960 (13)	0.81469 (15)	0.17864 (9)	0.0434 (4)
N2	0.52356 (13)	0.83599 (16)	0.25133 (9)	0.0475 (4)
O1	0.03516 (15)	0.73016 (17)	0.06980 (10)	0.0708 (5)
O2	0.29362 (12)	0.66240 (13)	0.13240 (9)	0.0511 (4)
O3	0.26535 (15)	0.98497 (17)	0.06915 (9)	0.0666 (5)
O4	0.24443 (15)	1.04707 (14)	0.17193 (10)	0.0616 (5)
O5	0.55371 (16)	0.84351 (15)	0.10714 (10)	0.0639 (5)
O6	0.48258 (15)	1.06910 (16)	0.28235 (10)	0.0658 (5)
O7	−0.21005 (14)	1.05041 (18)	0.25026 (11)	0.0750 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0365 (10)	0.0494 (12)	0.0561 (12)	−0.0029 (9)	0.0085 (9)	−0.0051 (10)
C2	0.0376 (10)	0.0395 (11)	0.0607 (12)	−0.0051 (8)	0.0145 (9)	−0.0032 (9)
C3	0.0311 (9)	0.0451 (11)	0.0476 (10)	−0.0006 (8)	0.0102 (8)	0.0025 (9)
C4	0.0309 (8)	0.0410 (11)	0.0427 (10)	−0.0004 (7)	0.0084 (7)	−0.0009 (8)
C5	0.0338 (9)	0.0499 (12)	0.0512 (11)	0.0008 (8)	0.0083 (8)	0.0021 (9)
C6	0.0541 (14)	0.101 (2)	0.0501 (13)	0.0124 (14)	0.0131 (11)	0.0156 (14)
C7	0.0630 (17)	0.109 (3)	0.0643 (17)	−0.0003 (17)	−0.0024 (13)	0.0053 (17)
C8	0.0395 (12)	0.100 (2)	0.0647 (15)	−0.0042 (13)	−0.0028 (11)	0.0059 (15)
C9	0.0309 (9)	0.0485 (12)	0.0448 (10)	−0.0033 (8)	0.0109 (7)	−0.0059 (9)
C10	0.0308 (8)	0.0401 (10)	0.0425 (10)	−0.0036 (7)	0.0077 (7)	−0.0026 (8)
C11	0.0322 (9)	0.0539 (13)	0.0558 (12)	−0.0035 (9)	0.0135 (8)	−0.0120 (10)
C12	0.0351 (10)	0.0510 (13)	0.0590 (13)	−0.0064 (9)	0.0085 (9)	−0.0057 (10)
C13	0.0658 (16)	0.0542 (15)	0.0807 (18)	−0.0097 (12)	0.0118 (14)	−0.0094 (13)
C14	0.089 (2)	0.0647 (18)	0.090 (2)	−0.0250 (16)	0.0134 (18)	0.0087 (17)
C15	0.0711 (18)	0.087 (2)	0.0725 (18)	−0.0257 (16)	0.0138 (14)	0.0177 (17)
C16	0.0476 (12)	0.0776 (18)	0.0566 (13)	−0.0120 (12)	0.0137 (10)	0.0049 (12)
C17	0.0311 (9)	0.0563 (13)	0.0512 (11)	−0.0050 (9)	0.0086 (8)	0.0012 (10)
C18	0.0327 (9)	0.0529 (12)	0.0485 (11)	0.0011 (8)	0.0131 (8)	−0.0045 (9)
C19	0.0340 (9)	0.0434 (11)	0.0495 (11)	−0.0026 (8)	0.0105 (8)	0.0019 (9)
C20	0.088 (2)	0.098 (3)	0.0670 (17)	0.0316 (19)	0.0052 (15)	0.0254 (17)
C21A	0.133 (6)	0.068 (4)	0.107 (5)	0.023 (4)	0.011 (4)	0.022 (3)
C21B	0.080 (6)	0.141 (10)	0.129 (9)	0.019 (6)	0.001 (6)	0.055 (8)
C22	0.0487 (11)	0.0448 (12)	0.0528 (12)	−0.0033 (9)	0.0123 (9)	−0.0031 (10)
C23	0.0611 (14)	0.0724 (18)	0.0618 (14)	−0.0109 (13)	0.0226 (12)	−0.0083 (13)
C24	0.100 (2)	0.118 (3)	0.089 (2)	−0.022 (2)	0.053 (2)	−0.040 (2)
C25	0.130 (3)	0.118 (3)	0.094 (2)	−0.044 (3)	0.054 (2)	−0.059 (2)
C26	0.091 (2)	0.086 (2)	0.094 (2)	−0.0354 (18)	0.0343 (19)	−0.0377 (19)
C27	0.0583 (14)	0.0573 (15)	0.0752 (16)	−0.0134 (12)	0.0231 (12)	−0.0146 (13)
C28	0.0328 (9)	0.0461 (11)	0.0500 (11)	0.0008 (8)	0.0103 (8)	0.0046 (9)
C29	0.0388 (11)	0.0800 (18)	0.0580 (13)	0.0066 (11)	0.0023 (10)	−0.0167 (12)
C30	0.0341 (11)	0.100 (2)	0.0713 (16)	0.0126 (12)	−0.0011 (11)	−0.0178 (15)
C31	0.0366 (10)	0.0601 (14)	0.0599 (13)	0.0074 (9)	0.0137 (9)	0.0025 (11)
C32	0.0401 (11)	0.0583 (14)	0.0641 (14)	−0.0066 (10)	0.0155 (10)	−0.0128 (11)
C33	0.0306 (9)	0.0584 (14)	0.0709 (15)	−0.0067 (9)	0.0098 (9)	−0.0141 (12)
C34	0.0636 (16)	0.082 (2)	0.0797 (19)	0.0160 (14)	0.0285 (14)	−0.0077 (15)
N1	0.0304 (8)	0.0476 (10)	0.0494 (9)	−0.0001 (7)	0.0061 (7)	−0.0033 (8)
N2	0.0293 (8)	0.0623 (12)	0.0488 (10)	0.0019 (7)	0.0073 (7)	0.0034 (8)
O1	0.0556 (10)	0.0786 (13)	0.0656 (11)	0.0073 (9)	−0.0046 (8)	−0.0213 (10)
O2	0.0393 (7)	0.0479 (9)	0.0687 (10)	−0.0074 (6)	0.0192 (7)	−0.0137 (7)
O3	0.0678 (11)	0.0783 (13)	0.0503 (9)	0.0240 (9)	0.0105 (8)	0.0119 (9)
O4	0.0674 (11)	0.0517 (10)	0.0673 (11)	0.0153 (8)	0.0215 (9)	0.0030 (8)
O5	0.0721 (11)	0.0602 (11)	0.0690 (11)	0.0061 (9)	0.0357 (9)	−0.0104 (9)
O6	0.0601 (10)	0.0743 (12)	0.0706 (11)	−0.0127 (9)	0.0307 (9)	−0.0277 (9)
O7	0.0414 (9)	0.0941 (15)	0.0896 (13)	0.0143 (9)	0.0183 (9)	−0.0205 (11)

Geometric parameters (Å, º) top

C1—O1	1.205 (3)	C19—O4	1.201 (3)
C1—N1	1.359 (3)	C19—O3	1.321 (3)
C1—C2	1.522 (3)	C20—C21B	1.489 (11)
C2—O2	1.408 (2)	C20—O3	1.462 (3)
C2—C3	1.554 (3)	C20—C21A	1.4690
C2—H2	0.9800	C20—H20A	0.9700
C3—N1	1.483 (3)	C20—H20B	0.9700
C3—C4	1.521 (3)	C20—H20C	0.9700
C3—H3	0.9800	C20—H20D	0.9700
C4—C10	1.529 (3)	C21A—H21A	0.9600
C4—C5	1.528 (3)	C21A—H21B	0.9600
C4—H4	0.9800	C21A—H21C	0.9600
C5—N2	1.468 (3)	C21B—H21D	0.9600
C5—C6	1.520 (3)	C21B—H21E	0.9600
C5—H5	0.9800	C21B—H21F	0.9600
C6—C7	1.519 (4)	C22—C23	1.376 (3)
C6—H6A	0.9700	C22—O2	1.377 (3)
C6—H6B	0.9700	C22—C27	1.380 (3)
C7—C8	1.497 (4)	C23—C24	1.369 (4)
C7—H7A	0.9700	C23—H23	0.9300
C7—H7B	0.9700	C24—C25	1.378 (5)
C8—N2	1.470 (3)	C24—H24	0.9300
C8—H8A	0.9700	C25—C26	1.368 (5)
C8—H8B	0.9700	C25—H25	0.9300
C9—N2	1.437 (3)	C26—C27	1.364 (4)
C9—C11	1.539 (3)	C26—H26	0.9300
C9—C18	1.544 (3)	C27—H27	0.9300
C9—C10	1.564 (3)	C28—C33	1.363 (3)
C10—C19	1.503 (3)	C28—C29	1.388 (3)
C10—H10	0.9800	C28—N1	1.415 (3)
C11—O6	1.207 (3)	C29—C30	1.366 (4)
C11—C12	1.476 (3)	C29—H29	0.9300
C12—C13	1.385 (4)	C30—C31	1.384 (4)
C12—C17	1.385 (3)	C30—H30	0.9300
C13—C14	1.370 (5)	C31—O7	1.365 (3)
C13—H13	0.9300	C31—C32	1.370 (3)
C14—C15	1.379 (5)	C32—C33	1.385 (3)
C14—H14	0.9300	C32—H32	0.9300
C15—C16	1.367 (4)	C33—H33	0.9300
C15—H15	0.9300	C34—O7	1.405 (4)
C16—C17	1.389 (3)	C34—H34A	0.9600
C16—H16	0.9300	C34—H34B	0.9600
C17—C18	1.471 (3)	C34—H34C	0.9600
C18—O5	1.201 (3)

O1—C1—N1	132.1 (2)	C21B—C20—O3	108.2 (5)
O1—C1—C2	135.9 (2)	C21B—C20—C21A	142.3 (5)
N1—C1—C2	92.01 (17)	O3—C20—C21A	108.85 (17)
O2—C2—C1	117.96 (19)	C21B—C20—H20A	49.7
O2—C2—C3	117.93 (16)	O3—C20—H20A	109.9
C1—C2—C3	86.24 (16)	C21A—C20—H20A	109.9
O2—C2—H2	110.9	C21B—C20—H20B	62.3
C1—C2—H2	110.9	O3—C20—H20B	109.9
C3—C2—H2	110.9	C21A—C20—H20B	109.9
N1—C3—C4	116.81 (17)	H20A—C20—H20B	108.3
N1—C3—C2	86.19 (15)	C21B—C20—H20C	110.1
C4—C3—C2	120.41 (17)	O3—C20—H20C	110.1
N1—C3—H3	110.4	C21A—C20—H20C	49.7
C4—C3—H3	110.4	H20A—C20—H20C	62.9
C2—C3—H3	110.4	H20B—C20—H20C	139.5
C3—C4—C10	116.51 (16)	C21B—C20—H20D	110.1
C3—C4—C5	112.06 (17)	O3—C20—H20D	110.1
C10—C4—C5	103.33 (15)	C21A—C20—H20D	62.2
C3—C4—H4	108.2	H20A—C20—H20D	139.5
C10—C4—H4	108.2	H20B—C20—H20D	50.5
C5—C4—H4	108.2	H20C—C20—H20D	108.4
N2—C5—C6	105.00 (18)	C20—C21A—H21A	109.5
N2—C5—C4	105.16 (17)	C20—C21A—H21B	109.5
C6—C5—C4	118.62 (19)	H21A—C21A—H21B	109.5
N2—C5—H5	109.2	C20—C21A—H21C	109.5
C6—C5—H5	109.2	H21A—C21A—H21C	109.5
C4—C5—H5	109.2	H21B—C21A—H21C	109.5
C5—C6—C7	102.5 (2)	C20—C21B—H21D	109.5
C5—C6—H6A	111.3	C20—C21B—H21E	109.5
C7—C6—H6A	111.3	H21D—C21B—H21E	109.5
C5—C6—H6B	111.3	C20—C21B—H21F	109.5
C7—C6—H6B	111.3	H21D—C21B—H21F	109.5
H6A—C6—H6B	109.2	H21E—C21B—H21F	109.5
C8—C7—C6	104.1 (2)	C23—C22—O2	115.0 (2)
C8—C7—H7A	110.9	C23—C22—C27	120.5 (2)
C6—C7—H7A	110.9	O2—C22—C27	124.6 (2)
C8—C7—H7B	110.9	C22—C23—C24	119.0 (3)
C6—C7—H7B	110.9	C22—C23—H23	120.5
H7A—C7—H7B	109.0	C24—C23—H23	120.5
N2—C8—C7	104.5 (2)	C23—C24—C25	120.5 (3)
N2—C8—H8A	110.9	C23—C24—H24	119.7
C7—C8—H8A	110.9	C25—C24—H24	119.7
N2—C8—H8B	110.9	C26—C25—C24	120.2 (3)
C7—C8—H8B	110.9	C26—C25—H25	119.9
H8A—C8—H8B	108.9	C24—C25—H25	119.9
N2—C9—C11	118.21 (17)	C25—C26—C27	119.8 (3)
N2—C9—C18	113.43 (17)	C25—C26—H26	120.1
C11—C9—C18	102.45 (17)	C27—C26—H26	120.1
N2—C9—C10	102.57 (16)	C26—C27—C22	120.1 (3)
C11—C9—C10	111.24 (16)	C26—C27—H27	120.0
C18—C9—C10	108.94 (16)	C22—C27—H27	120.0
C19—C10—C4	113.86 (16)	C33—C28—C29	119.4 (2)
C19—C10—C9	113.61 (17)	C33—C28—N1	121.92 (18)
C4—C10—C9	102.83 (15)	C29—C28—N1	118.6 (2)
C19—C10—H10	108.8	C30—C29—C28	119.9 (2)
C4—C10—H10	108.8	C30—C29—H29	120.1
C9—C10—H10	108.8	C28—C29—H29	120.1
O6—C11—C12	126.1 (2)	C29—C30—C31	120.8 (2)
O6—C11—C9	125.9 (2)	C29—C30—H30	119.6
C12—C11—C9	107.97 (18)	C31—C30—H30	119.6
C13—C12—C17	120.7 (2)	O7—C31—C32	124.8 (2)
C13—C12—C11	129.3 (2)	O7—C31—C30	116.1 (2)
C17—C12—C11	110.0 (2)	C32—C31—C30	119.2 (2)
C14—C13—C12	117.9 (3)	C31—C32—C33	120.1 (2)
C14—C13—H13	121.0	C31—C32—H32	120.0
C12—C13—H13	121.0	C33—C32—H32	120.0
C13—C14—C15	121.4 (3)	C28—C33—C32	120.7 (2)
C13—C14—H14	119.3	C28—C33—H33	119.7
C15—C14—H14	119.3	C32—C33—H33	119.7
C16—C15—C14	121.3 (3)	O7—C34—H34A	109.5
C16—C15—H15	119.4	O7—C34—H34B	109.5
C14—C15—H15	119.4	H34A—C34—H34B	109.5
C15—C16—C17	117.9 (3)	O7—C34—H34C	109.5
C15—C16—H16	121.0	H34A—C34—H34C	109.5
C17—C16—H16	121.0	H34B—C34—H34C	109.5
C16—C17—C12	120.7 (2)	C1—N1—C28	129.38 (17)
C16—C17—C18	128.8 (2)	C1—N1—C3	95.32 (16)
C12—C17—C18	110.47 (19)	C28—N1—C3	130.41 (17)
O5—C18—C17	127.1 (2)	C9—N2—C5	112.32 (15)
O5—C18—C9	125.1 (2)	C9—N2—C8	120.9 (2)
C17—C18—C9	107.81 (18)	C5—N2—C8	109.91 (18)
O4—C19—O3	124.3 (2)	C22—O2—C2	116.54 (16)
O4—C19—C10	124.9 (2)	C19—O3—C20	116.7 (2)
O3—C19—C10	110.83 (18)	C31—O7—C34	118.0 (2)

O1—C1—C2—O2	58.3 (4)	C11—C9—C18—C17	−10.5 (2)
N1—C1—C2—O2	−123.46 (19)	C10—C9—C18—C17	107.36 (19)
O1—C1—C2—C3	178.1 (3)	C4—C10—C19—O4	33.5 (3)
N1—C1—C2—C3	−3.69 (16)	C9—C10—C19—O4	−83.8 (3)
O2—C2—C3—N1	123.2 (2)	C4—C10—C19—O3	−147.20 (18)
C1—C2—C3—N1	3.39 (15)	C9—C10—C19—O3	95.5 (2)
O2—C2—C3—C4	4.2 (3)	O2—C22—C23—C24	−179.9 (3)
C1—C2—C3—C4	−115.6 (2)	C27—C22—C23—C24	−0.5 (4)
N1—C3—C4—C10	−54.3 (2)	C22—C23—C24—C25	0.1 (6)
C2—C3—C4—C10	47.9 (3)	C23—C24—C25—C26	0.0 (7)
N1—C3—C4—C5	−172.95 (17)	C24—C25—C26—C27	0.3 (7)
C2—C3—C4—C5	−70.8 (2)	C25—C26—C27—C22	−0.7 (6)
C3—C4—C5—N2	150.00 (17)	C23—C22—C27—C26	0.8 (4)
C10—C4—C5—N2	23.8 (2)	O2—C22—C27—C26	−179.9 (3)
C3—C4—C5—C6	−93.0 (3)	C33—C28—C29—C30	0.9 (4)
C10—C4—C5—C6	140.7 (2)	N1—C28—C29—C30	177.6 (3)
N2—C5—C6—C7	−29.2 (3)	C28—C29—C30—C31	0.3 (5)
C4—C5—C6—C7	−146.3 (2)	C29—C30—C31—O7	179.4 (3)
C5—C6—C7—C8	37.7 (3)	C29—C30—C31—C32	−1.1 (4)
C6—C7—C8—N2	−31.8 (3)	O7—C31—C32—C33	−179.8 (2)
C3—C4—C10—C19	77.5 (2)	C30—C31—C32—C33	0.8 (4)
C5—C4—C10—C19	−159.12 (17)	C29—C28—C33—C32	−1.2 (4)
C3—C4—C10—C9	−159.09 (17)	N1—C28—C33—C32	−177.8 (2)
C5—C4—C10—C9	−35.8 (2)	C31—C32—C33—C28	0.3 (4)
N2—C9—C10—C19	158.22 (17)	O1—C1—N1—C28	25.5 (4)
C11—C9—C10—C19	30.9 (2)	C2—C1—N1—C28	−152.9 (2)
C18—C9—C10—C19	−81.3 (2)	O1—C1—N1—C3	−177.8 (3)
N2—C9—C10—C4	34.68 (19)	C2—C1—N1—C3	3.88 (17)
C11—C9—C10—C4	−92.64 (19)	C33—C28—N1—C1	179.3 (2)
C18—C9—C10—C4	155.16 (17)	C29—C28—N1—C1	2.7 (4)
N2—C9—C11—O6	−42.0 (3)	C33—C28—N1—C3	30.4 (3)
C18—C9—C11—O6	−167.5 (2)	C29—C28—N1—C3	−146.2 (2)
C10—C9—C11—O6	76.2 (3)	C4—C3—N1—C1	118.5 (2)
N2—C9—C11—C12	136.57 (18)	C2—C3—N1—C1	−3.80 (17)
C18—C9—C11—C12	11.1 (2)	C4—C3—N1—C28	−85.1 (3)
C10—C9—C11—C12	−105.17 (18)	C2—C3—N1—C28	152.6 (2)
O6—C11—C12—C13	−8.3 (4)	C11—C9—N2—C5	102.0 (2)
C9—C11—C12—C13	173.2 (2)	C18—C9—N2—C5	−138.09 (18)
O6—C11—C12—C17	170.6 (2)	C10—C9—N2—C5	−20.8 (2)
C9—C11—C12—C17	−8.0 (2)	C11—C9—N2—C8	−30.4 (3)
C17—C12—C13—C14	−0.8 (4)	C18—C9—N2—C8	89.5 (2)
C11—C12—C13—C14	178.0 (2)	C10—C9—N2—C8	−153.2 (2)
C12—C13—C14—C15	0.0 (5)	C6—C5—N2—C9	−127.4 (2)
C13—C14—C15—C16	0.6 (5)	C4—C5—N2—C9	−1.5 (2)
C14—C15—C16—C17	−0.3 (4)	C6—C5—N2—C8	10.2 (3)
C15—C16—C17—C12	−0.5 (3)	C4—C5—N2—C8	136.1 (2)
C15—C16—C17—C18	−179.1 (2)	C7—C8—N2—C9	146.9 (2)
C13—C12—C17—C16	1.0 (3)	C7—C8—N2—C5	13.5 (3)
C11—C12—C17—C16	−177.95 (19)	C23—C22—O2—C2	176.5 (2)
C13—C12—C17—C18	179.9 (2)	C27—C22—O2—C2	−2.9 (3)
C11—C12—C17—C18	0.9 (2)	C1—C2—O2—C22	−75.8 (2)
C16—C17—C18—O5	4.5 (4)	C3—C2—O2—C22	−177.18 (18)
C12—C17—C18—O5	−174.2 (2)	O4—C19—O3—C20	−1.9 (4)
C16—C17—C18—C9	−174.8 (2)	C10—C19—O3—C20	178.8 (2)
C12—C17—C18—C9	6.4 (2)	C21B—C20—O3—C19	−86.4 (6)
N2—C9—C18—O5	41.5 (3)	C21A—C20—O3—C19	86.9 (2)
C11—C9—C18—O5	170.1 (2)	C32—C31—O7—C34	4.3 (4)
C10—C9—C18—O5	−72.0 (3)	C30—C31—O7—C34	−176.3 (3)
N2—C9—C18—C17	−139.10 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O6ⁱ	0.98	2.45	3.151 (3)	129
C26—H26···O1ⁱⁱ	0.93	2.50	3.390 (4)	160
C8—H8A···O6	0.97	2.50	3.166 (4)	126
C10—H10···O2	0.98	2.24	2.987 (3)	132
C29—H29···O1	0.93	2.40	3.024 (3)	125

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

Experimental details

Crystal data
Chemical formula	C₃₄H₃₂N₂O₇
M_r	580.62
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	12.4776 (7), 12.4946 (6), 19.4958 (11)
β (°)	106.013 (3)
V (Å³)	2921.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.973, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	66713, 7446, 4654
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.675

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.225, 0.92
No. of reflections	7446
No. of parameters	395
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.25

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O6ⁱ	0.98	2.45	3.151 (3)	129
C26—H26···O1ⁱⁱ	0.93	2.50	3.390 (4)	160
C8—H8A···O6	0.97	2.50	3.166 (4)	126
C10—H10···O2	0.98	2.24	2.987 (3)	132
C29—H29···O1	0.93	2.40	3.024 (3)	125

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

Acknowledgements

ETSK thanks Professor M. N. Ponnuswamy and Professor D. Velmurugan, Department of Crystallography and Biophysics, University of Madras, India, for their guidance and valuable suggestions, and SRM Management for their support.

References

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages o1832-o1833

doi:10.1107/S1600536808026913

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

Ethyl 1'-[1-(4-methoxyphenyl)-3-phen­oxy-4-phenylazetidin-1-yl]-1,3-dioxo-2′,3′,5′,6′,7′,7a′-hexa­hydroindan-2-spiro-3′-1′H-pyrrolizine-2′-carboxylate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 1'-[1-(4-methoxyphenyl)-3-phenoxy-4-phenylazetidin-1-yl]-1,3-dioxo-2′,3′,5′,6′,7′,7a′-hexahydroindan-2-spiro-3′-1′H-pyrrolizine-2′-carboxylate