Methyl 3-(2-chlorophenyl)-2-(1H-indol-3-ylmethyl)-5-[1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-4-nitropyr­rolidine-2-carboxylate

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

doi:10.1107/S1600536808013585

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages o1070-o1071

doi:10.1107/S1600536808013585

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Methyl 3-(2-chlorophenyl)-2-(1H-indol-3-ylmethyl)-5-[1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-4-nitropyrrolidine-2-carboxylate

S. Nirmala,^a E. Theboral Sugi Kamala,^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 1 May 2008; accepted 7 May 2008; online 14 May 2008)

In the molecule of the title compound, C₃₇H₃₃ClN₄O₆, the four-membered β-lactam ring is essentially planar and is oriented at dihedral angles of 30.0 (1), 76.3 (1) and 30.9 (1)° with respect to the methoxyphenyl ring, the phenyl ring and the indole unit, respectively. The pyrrolidine ring adopts a twist conformation. Intramolecular C—H⋯Cl and C—H⋯O hydrogen bonds result in the formation of two five- and one six-membered rings. In the crystal structure, intermolecular C—H⋯O and N—H⋯O hydrogen bonds link the molecules. A weak π⋯π interaction between the pyrrole rings further stabilizes the structure, with a centroid–centroid distance of 3.806 (2) Å.

Related literature

For general background, see: Bruggink (2001 ); Morin & Gorman (1982 ); Katritzky et al. (1996 ); Georg (1993 ); Coyne et al. (2007 ); Dobrowolski et al. (2004 ); Cha et al. (2006 ). For related literature, see: Bhaskaran et al. (2006 ); Kamala et al. (2008 ); Ülkü et al. (1997 ). For ring puckering parameters, see: Cremer & Pople (1975 ). For asymmetry parameters, see: Nardelli (1995 ).

Experimental

Crystal data

C₃₇H₃₃ClN₄O₆
M_r = 665.12
Triclinic, $[P \overline 1]$
a = 10.399 (3) Å
b = 12.500 (3) Å
c = 14.211 (3) Å
α = 93.766 (6)°
β = 99.962 (6)°
γ = 114.066 (5)°
V = 1642.1 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 293 (2) K
0.30 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEX2 CCD diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.951, T_max = 0.973
25481 measured reflections
5563 independent reflections
3770 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.317
S = 1.10
5563 reflections
433 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cl1	0.98	2.57	3.095 (4)	114
C11—H11⋯O3	0.98	2.37	2.786 (4)	105
C22—H22⋯O5	0.93	2.59	3.080 (6)	113
C14—H14⋯O4ⁱ	0.98	2.53	3.443 (5)	154
C34—H34⋯O4ⁱⁱ	0.93	2.59	3.414 (6)	148
N1—H1A⋯O6ⁱⁱⁱ	0.86	2.14	2.982 (5)	167
Symmetry codes: (i) -x, -y, -z; (ii) -x, -y+1, -z; (iii) -x+1, -y, -z+1.

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: SIR92 (Altomare et al., 1993 ); 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/S1600536808013585/hk2460sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013585/hk2460Isup2.hkl

checkCIF report

Comment top

β-Lactams are one of the best known and most extensively studied class of compounds due to their biological activity (Bruggink, 2001; Morin & Gorman, 1982; Katritzky et al., 1996; Georg, 1993). The β-lactam class of drugs have revolutionized treatment in medicine (Coyne et al., 2007). In the late 1970's and early 1980's, the first class of the monocyclic β-lactam antibacterial agents were found in natural sources (Dobrowolski et al., 2004). All β-lactams are based on a β-lactam ring responsible for the antibacterial activity and variable side chains that account for the major differences in their chemical and pharmocological properties (Cha et al., 2006). We report herein the crystal structure of the title compound, (I).

In the title compound, (I), (Fig. 1) the four-membered β-lactam ring A (N4/C14-C16) is nearly planar, with a maximum deviation of 0.038 (4) Å for atom N1. The C14-C15 [1.581 (4) Å] and C15-C16 [1.523 (5) Å] bonds agree with those observed in similar structures (Bhaskaran et al., 2006; Kamala et al., 2008). The C14-C15-C16 [84.6 (2)°] bond angle is comparable to the corresponding value [87.0 (3)°)] in a related structure (Ülkü et al., 1997). The sum of the bond angles around atom N4 [355.6 (3)°] indicates sp² hybridization. The planar rings A, B (C17-C22) and C (C24-C29) are oriented at dihedral angles of A/B = 30.0 (1)°, A/C = 76.3 (1)° and B/C = 50.2 (1)°. The planar indole moiety is oriented with respect to rings A, C and D (C30-C35) at dihedral angles of 30.9 (1)°, 73.0 (1)° and 70.7 (1)°, respectively. The pyrrolidine ring E (N2/C10-C13) adopts a twisted conformation, with asymmetry [ΔC₂ (C11) = 0.011 (1), ΔC_s (C13) = 0.085 (2)] (Nardelli, 1995) and puckering [q₂ = 0.402 (3) Å and ϕ = -21.1 (4)°] (Cremer & Pople, 1975) parameters. Atom N2 deviates from the mean plane of (N2/C10-C12) by 0.553 (7) Å.

The intramolecular C-H···Cl and C-H···O hydrogen bonds (Table 1) result in the formation of two five- and one six-membered rings: F (O3/N3/C11/H11A/C12), G (Cl1/C11/H11/C30/C39) and H (O5/N4/C16/C17/C22/H22), respectively. In the crystal structure, intermolecular C-H···O and N-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. A weak π—π interaction between (N1/C1-C3/C8) rings at x, y, z and 1 - x, 1 - y, 1 - z further stabilize the structure, with a centroid-centroid distance of 3.806 (2) Å.

Related literature top

For general background, see: Bruggink (2001); Morin & Gorman (1982); Katritzky et al. (1996); Georg (1993); Coyne et al. (2007); Dobrowolski et al. (2004); Cha et al. (2006). For related literature, see: Bhaskaran et al. (2006); Kamala et al. (2008); Ülkü et al. (1997). For ring puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli (1995).

Experimental top

For the preparation of the title compound, β-Lactam aldehyde (1.0 mol) was treated with tryptophan methylester hydrochloride (1.0 mol) in the presence of Et₃N (2.5 mol) and anhydrous MgSO₄ (2.0 g) in dry dichloromethane (10 ml) at room temperature for 12 h to give the imine. The imine was washed with water and dried over Na₂SO₄. The solvent was evaporated under vacuum. The imine (1.0 mol) was then strirred with silver (I) acetate and p-chloro nitrostyrene (1.0 mol) in the presence of Et₃N (1.2 mol) and molecular sieves in dry toluene (30 ml) at room temperature for 12 h. The reaction mixture was filtered through a plug celite. The solvent was evaporated under reduced pressure and the residue was subjected to column chromatography on silica gel (100-200 mesh), with hexane-ethylacetate (7:3) as eluent to give the product. The compound was recrystallized from 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: SIR92 (Altomare et al., 1993); 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 the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. A partial packing diagram for (I). Hydrogen bonds are shown as dashed lines. H atoms not involed in hydrogen bondings have been omitted for clarity.

Methyl 3-(2-chlorophenyl)-2-(1H-indol-3-ylmethyl)-5-[1-(4-methoxyphenyl)-4-oxo- 3-phenylazetidin-2-yl]-4-nitropyrrolidine-2-carboxylate top

Crystal data top

C₃₇H₃₃ClN₄O₆	Z = 2
M_r = 665.12	F(000) = 696
Triclinic, P1	D_x = 1.345 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.399 (3) Å	Cell parameters from 8315 reflections
b = 12.500 (3) Å	θ = 2.5–31.6°
c = 14.211 (3) Å	µ = 0.17 mm⁻¹
α = 93.766 (6)°	T = 293 K
β = 99.962 (6)°	Prism, colourless
γ = 114.066 (5)°	0.30 × 0.20 × 0.16 mm
V = 1642.1 (7) Å³

Data collection top

Bruker KAPPA APEX2 CCD diffractometer	5563 independent reflections
Radiation source: fine-focus sealed tube	3770 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ω and ϕ scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (Blessing, 1995)	h = −12→12
T_min = 0.951, T_max = 0.973	k = −14→14
25481 measured reflections	l = −16→16

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.317	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
5563 reflections	(Δ/σ)_max < 0.001
433 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

C₃₇H₃₃ClN₄O₆	γ = 114.066 (5)°
M_r = 665.12	V = 1642.1 (7) Å³
Triclinic, P1	Z = 2
a = 10.399 (3) Å	Mo Kα radiation
b = 12.500 (3) Å	µ = 0.17 mm⁻¹
c = 14.211 (3) Å	T = 293 K
α = 93.766 (6)°	0.30 × 0.20 × 0.16 mm
β = 99.962 (6)°

Data collection top

Bruker KAPPA APEX2 CCD diffractometer	5563 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	3770 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.973	R_int = 0.057
25481 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.317	H-atom parameters constrained
S = 1.10	Δρ_max = 0.51 e Å⁻³
5563 reflections	Δρ_min = −0.64 e Å⁻³
433 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 > 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
Cl1	0.27147 (16)	0.62053 (13)	0.03791 (11)	0.0912 (5)
O1	0.4619 (3)	0.3522 (3)	0.1048 (2)	0.0620 (8)
O2	0.4973 (3)	0.5325 (3)	0.16978 (19)	0.0549 (7)
O3	0.1219 (3)	0.2147 (3)	−0.0280 (2)	0.0690 (9)
O4	−0.0986 (3)	0.1137 (3)	−0.02304 (19)	0.0646 (8)
O5	−0.1691 (3)	−0.1217 (3)	0.3043 (3)	0.0861 (12)
O6	0.4562 (3)	−0.1339 (3)	0.4179 (2)	0.0647 (9)
N1	0.5503 (4)	0.3211 (3)	0.4608 (2)	0.0500 (8)
H1A	0.5602	0.2674	0.4921	0.060*
N2	0.2433 (3)	0.2437 (2)	0.19400 (18)	0.0340 (6)
H2	0.2943	0.2039	0.1976	0.041*
N3	0.0198 (3)	0.1926 (3)	0.0102 (2)	0.0441 (8)
N4	0.0375 (3)	0.0089 (2)	0.2561 (2)	0.0406 (7)
C1	0.4247 (4)	0.3105 (3)	0.4029 (2)	0.0452 (9)
H1	0.3372	0.2435	0.3914	0.054*
C2	0.4455 (3)	0.4115 (3)	0.3646 (2)	0.0344 (7)
C3	0.5947 (3)	0.4900 (3)	0.4004 (2)	0.0355 (8)
C4	0.6834 (4)	0.6067 (3)	0.3897 (2)	0.0464 (9)
H4	0.6465	0.6488	0.3504	0.056*
C5	0.8251 (4)	0.6574 (4)	0.4383 (3)	0.0614 (11)
H5	0.8838	0.7347	0.4320	0.074*
C6	0.8836 (4)	0.5963 (5)	0.4969 (3)	0.0669 (13)
H6	0.9802	0.6335	0.5289	0.080*
C7	0.8008 (4)	0.4815 (5)	0.5083 (3)	0.0592 (12)
H7	0.8402	0.4400	0.5465	0.071*
C8	0.6570 (4)	0.4301 (3)	0.4609 (2)	0.0411 (8)
C9	0.3323 (3)	0.4348 (3)	0.3002 (2)	0.0340 (7)
H9A	0.3665	0.5194	0.2999	0.041*
H9B	0.2457	0.4079	0.3260	0.041*
C10	0.2943 (3)	0.3712 (3)	0.1948 (2)	0.0310 (7)
C11	0.1669 (3)	0.3868 (3)	0.1245 (2)	0.0335 (7)
H11	0.1957	0.4033	0.0630	0.040*
C12	0.0405 (3)	0.2628 (3)	0.1066 (2)	0.0331 (7)
H12	−0.0490	0.2678	0.1139	0.040*
C13	0.0886 (3)	0.1980 (3)	0.1857 (2)	0.0315 (7)
H13	0.0732	0.2268	0.2468	0.038*
C14	0.0125 (3)	0.0649 (3)	0.1707 (2)	0.0357 (7)
H14	0.0309	0.0299	0.1137	0.043*
C15	−0.1531 (3)	0.0061 (3)	0.1733 (3)	0.0458 (9)
H15	−0.2101	−0.0532	0.1159	0.055*
C16	−0.1057 (4)	−0.0505 (3)	0.2560 (3)	0.0519 (10)
C17	0.1534 (3)	−0.0169 (3)	0.2985 (2)	0.0378 (8)
C18	0.2642 (3)	−0.0060 (3)	0.2526 (2)	0.0393 (8)
H18	0.2685	0.0256	0.1952	0.047*
C19	0.3685 (3)	−0.0420 (3)	0.2917 (3)	0.0430 (8)
H19	0.4434	−0.0337	0.2610	0.052*
C20	0.3619 (4)	−0.0899 (3)	0.3756 (3)	0.0460 (9)
C21	0.2550 (4)	−0.0962 (4)	0.4239 (3)	0.0544 (10)
H21	0.2533	−0.1250	0.4826	0.065*
C22	0.1513 (4)	−0.0600 (4)	0.3857 (3)	0.0509 (10)
H22	0.0796	−0.0645	0.4185	0.061*
C23	0.5611 (5)	−0.1357 (5)	0.3669 (4)	0.0807 (16)
H23A	0.6198	−0.1683	0.4029	0.121*
H23B	0.6208	−0.0564	0.3585	0.121*
H23C	0.5137	−0.1838	0.3048	0.121*
C24	−0.2264 (3)	0.0835 (3)	0.1965 (3)	0.0418 (9)
C25	−0.1948 (4)	0.1455 (3)	0.2876 (3)	0.0461 (9)
H25	−0.1276	0.1389	0.3365	0.055*
C26	−0.2613 (4)	0.2174 (4)	0.3075 (3)	0.0555 (10)
H26	−0.2388	0.2582	0.3696	0.067*
C27	−0.3605 (4)	0.2289 (4)	0.2362 (3)	0.0605 (11)
H27	−0.4052	0.2774	0.2495	0.073*
C28	−0.3929 (4)	0.1674 (4)	0.1442 (3)	0.0618 (12)
H28	−0.4591	0.1752	0.0953	0.074*
C29	−0.3278 (4)	0.0951 (4)	0.1250 (3)	0.0537 (10)
H29	−0.3517	0.0531	0.0632	0.064*
C30	0.1230 (3)	0.4815 (3)	0.1585 (2)	0.0386 (8)
C31	0.0321 (4)	0.4623 (4)	0.2234 (3)	0.0473 (9)
H31	0.0003	0.3906	0.2472	0.057*
C32	−0.0116 (5)	0.5464 (4)	0.2530 (3)	0.0664 (13)
H32	−0.0731	0.5307	0.2957	0.080*
C33	0.0349 (7)	0.6529 (5)	0.2198 (4)	0.0842 (18)
H33	0.0062	0.7101	0.2406	0.101*
C34	0.1243 (6)	0.6751 (4)	0.1557 (4)	0.0775 (16)
H34	0.1564	0.7477	0.1333	0.093*
C35	0.1674 (4)	0.5889 (3)	0.1239 (3)	0.0537 (10)
C36	0.4283 (3)	0.4159 (3)	0.1513 (2)	0.0384 (8)
C37	0.6263 (4)	0.5862 (5)	0.1315 (3)	0.0768 (15)
H37A	0.6678	0.6708	0.1491	0.115*
H37B	0.6014	0.5664	0.0623	0.115*
H37C	0.6950	0.5570	0.1577	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1027 (10)	0.0749 (10)	0.1001 (11)	0.0317 (8)	0.0319 (8)	0.0577 (8)
O1	0.0716 (17)	0.076 (2)	0.0706 (19)	0.0510 (17)	0.0408 (14)	0.0291 (16)
O2	0.0497 (14)	0.0547 (19)	0.0521 (16)	0.0091 (13)	0.0214 (11)	0.0149 (13)
O3	0.081 (2)	0.083 (2)	0.0504 (17)	0.0411 (18)	0.0232 (15)	−0.0032 (16)
O4	0.0702 (18)	0.060 (2)	0.0491 (16)	0.0255 (16)	−0.0112 (13)	−0.0109 (14)
O5	0.0532 (16)	0.084 (2)	0.149 (3)	0.0374 (16)	0.0485 (19)	0.078 (2)
O6	0.0597 (15)	0.083 (2)	0.079 (2)	0.0484 (16)	0.0245 (14)	0.0487 (17)
N1	0.0702 (19)	0.057 (2)	0.0369 (16)	0.0401 (18)	0.0100 (14)	0.0201 (15)
N2	0.0349 (12)	0.0346 (16)	0.0398 (15)	0.0216 (12)	0.0076 (10)	0.0116 (12)
N3	0.0589 (18)	0.0459 (19)	0.0339 (16)	0.0323 (16)	0.0013 (13)	0.0045 (14)
N4	0.0355 (13)	0.0350 (17)	0.0586 (18)	0.0193 (12)	0.0137 (12)	0.0177 (14)
C1	0.0529 (18)	0.047 (2)	0.0362 (18)	0.0206 (17)	0.0092 (14)	0.0129 (17)
C2	0.0423 (16)	0.040 (2)	0.0277 (16)	0.0230 (15)	0.0104 (12)	0.0111 (14)
C3	0.0443 (16)	0.044 (2)	0.0240 (15)	0.0256 (15)	0.0068 (12)	0.0030 (14)
C4	0.0500 (18)	0.048 (2)	0.0393 (19)	0.0186 (17)	0.0110 (15)	0.0044 (17)
C5	0.049 (2)	0.058 (3)	0.061 (3)	0.0101 (19)	0.0095 (17)	−0.003 (2)
C6	0.0400 (18)	0.100 (4)	0.050 (2)	0.025 (2)	−0.0003 (16)	−0.003 (2)
C7	0.058 (2)	0.098 (4)	0.037 (2)	0.053 (3)	0.0016 (16)	0.006 (2)
C8	0.0518 (18)	0.050 (2)	0.0278 (16)	0.0287 (18)	0.0060 (13)	0.0033 (15)
C9	0.0360 (14)	0.0389 (19)	0.0332 (17)	0.0213 (14)	0.0092 (12)	0.0071 (14)
C10	0.0329 (14)	0.0348 (19)	0.0317 (16)	0.0195 (13)	0.0082 (11)	0.0103 (14)
C11	0.0425 (15)	0.0373 (19)	0.0281 (16)	0.0229 (14)	0.0091 (12)	0.0115 (14)
C12	0.0384 (15)	0.0376 (19)	0.0307 (16)	0.0239 (14)	0.0069 (12)	0.0046 (14)
C13	0.0357 (14)	0.0324 (18)	0.0315 (16)	0.0196 (13)	0.0070 (11)	0.0055 (13)
C14	0.0412 (15)	0.0311 (18)	0.0406 (18)	0.0221 (14)	0.0070 (12)	0.0050 (14)
C15	0.0375 (16)	0.039 (2)	0.064 (2)	0.0211 (15)	0.0078 (14)	0.0087 (17)
C16	0.0438 (18)	0.042 (2)	0.080 (3)	0.0235 (17)	0.0197 (18)	0.025 (2)
C17	0.0420 (16)	0.0296 (18)	0.0468 (19)	0.0188 (14)	0.0109 (14)	0.0120 (15)
C18	0.0402 (15)	0.037 (2)	0.0451 (19)	0.0187 (15)	0.0109 (13)	0.0159 (16)
C19	0.0431 (17)	0.043 (2)	0.051 (2)	0.0214 (16)	0.0180 (14)	0.0179 (17)
C20	0.0457 (17)	0.044 (2)	0.054 (2)	0.0232 (16)	0.0111 (15)	0.0234 (18)
C21	0.060 (2)	0.070 (3)	0.049 (2)	0.037 (2)	0.0207 (17)	0.033 (2)
C22	0.0537 (19)	0.061 (3)	0.052 (2)	0.0312 (19)	0.0237 (16)	0.0249 (19)
C23	0.070 (3)	0.103 (4)	0.116 (4)	0.066 (3)	0.043 (3)	0.063 (3)
C24	0.0356 (15)	0.038 (2)	0.057 (2)	0.0193 (14)	0.0119 (14)	0.0158 (17)
C25	0.0439 (17)	0.047 (2)	0.050 (2)	0.0210 (16)	0.0104 (15)	0.0155 (18)
C26	0.057 (2)	0.062 (3)	0.060 (2)	0.032 (2)	0.0248 (18)	0.017 (2)
C27	0.059 (2)	0.064 (3)	0.085 (3)	0.044 (2)	0.032 (2)	0.027 (2)
C28	0.057 (2)	0.080 (3)	0.071 (3)	0.047 (2)	0.0166 (19)	0.031 (2)
C29	0.0485 (18)	0.064 (3)	0.056 (2)	0.0327 (19)	0.0065 (16)	0.013 (2)
C30	0.0435 (16)	0.041 (2)	0.0355 (17)	0.0263 (15)	−0.0031 (13)	0.0077 (15)
C31	0.057 (2)	0.052 (2)	0.045 (2)	0.0381 (19)	0.0046 (15)	0.0036 (17)
C32	0.074 (3)	0.080 (3)	0.059 (3)	0.056 (3)	−0.004 (2)	−0.008 (2)
C33	0.106 (4)	0.064 (3)	0.090 (4)	0.067 (3)	−0.025 (3)	−0.019 (3)
C34	0.093 (3)	0.041 (3)	0.093 (4)	0.039 (3)	−0.020 (3)	0.007 (2)
C35	0.057 (2)	0.037 (2)	0.062 (2)	0.0219 (17)	−0.0066 (17)	0.0126 (18)
C36	0.0404 (16)	0.053 (2)	0.0320 (17)	0.0278 (17)	0.0102 (13)	0.0177 (16)
C37	0.052 (2)	0.097 (4)	0.061 (3)	0.004 (2)	0.024 (2)	0.027 (3)

Geometric parameters (Å, º) top

N1—H1A	0.8600	C17—C18	1.384 (5)
N2—H2	0.8600	C17—N4	1.418 (4)
N3—O4	1.208 (4)	C18—C19	1.382 (4)
N3—O3	1.215 (4)	C18—H18	0.9300
C1—C2	1.358 (5)	C19—C20	1.368 (5)
C1—N1	1.369 (4)	C19—H19	0.9300
C1—H1	0.9300	C20—O6	1.380 (4)
C2—C3	1.431 (5)	C20—C21	1.383 (5)
C2—C9	1.501 (4)	C21—C22	1.375 (5)
C3—C4	1.408 (5)	C21—H21	0.9300
C3—C8	1.417 (4)	C22—H22	0.9300
C4—C5	1.371 (5)	C23—O6	1.417 (5)
C4—H4	0.9300	C23—H23A	0.9600
C5—C6	1.390 (7)	C23—H23B	0.9600
C5—H5	0.9300	C23—H23C	0.9600
C6—C7	1.377 (7)	C24—C25	1.378 (5)
C6—H6	0.9300	C24—C29	1.392 (4)
C7—C8	1.383 (5)	C25—C26	1.380 (5)
C7—H7	0.9300	C25—H25	0.9300
C8—N1	1.362 (5)	C26—C27	1.376 (5)
C9—C10	1.553 (4)	C26—H26	0.9300
C9—H9A	0.9700	C27—C28	1.384 (6)
C9—H9B	0.9700	C27—H27	0.9300
C10—N2	1.459 (4)	C28—C29	1.373 (5)
C10—C36	1.531 (4)	C28—H28	0.9300
C10—C11	1.603 (3)	C29—H29	0.9300
C11—C30	1.511 (4)	C30—C35	1.385 (5)
C11—C12	1.538 (5)	C30—C31	1.395 (5)
C11—H11	0.9800	C31—C32	1.374 (5)
C12—N3	1.511 (4)	C31—H31	0.9300
C12—C13	1.558 (4)	C32—C33	1.365 (8)
C12—H12	0.9800	C32—H32	0.9300
C13—N2	1.451 (4)	C33—C34	1.374 (8)
C13—C14	1.503 (4)	C33—H33	0.9300
C13—H13	0.9800	C34—C35	1.402 (6)
C14—N4	1.478 (4)	C34—H34	0.9300
C14—C15	1.581 (4)	C35—Cl1	1.730 (5)
C14—H14	0.9800	C36—O1	1.197 (4)
C15—C24	1.507 (4)	C36—O2	1.319 (4)
C15—C16	1.523 (5)	C37—O2	1.454 (4)
C15—H15	0.9800	C37—H37A	0.9600
C16—O5	1.206 (5)	C37—H37B	0.9600
C16—N4	1.365 (4)	C37—H37C	0.9600
C17—C22	1.383 (5)

C36—O2—C37	116.4 (3)	C16—C15—C14	84.6 (2)
C20—O6—C23	116.9 (3)	C24—C15—H15	111.2
C8—N1—C1	109.2 (3)	C16—C15—H15	111.2
C8—N1—H1A	125.4	C14—C15—H15	111.2
C1—N1—H1A	125.4	O5—C16—N4	132.5 (3)
C13—N2—C10	105.6 (2)	O5—C16—C15	133.9 (3)
C13—N2—H2	127.2	N4—C16—C15	93.6 (3)
C10—N2—H2	127.2	C22—C17—C18	119.3 (3)
O4—N3—O3	123.6 (3)	C22—C17—N4	118.8 (3)
O4—N3—C12	116.9 (3)	C18—C17—N4	121.8 (3)
O3—N3—C12	119.5 (3)	C19—C18—C17	120.2 (3)
C16—N4—C17	128.4 (3)	C19—C18—H18	119.9
C16—N4—C14	94.5 (3)	C17—C18—H18	119.9
C17—N4—C14	132.7 (3)	C20—C19—C18	120.1 (3)
C2—C1—N1	110.6 (3)	C20—C19—H19	119.9
C2—C1—H1	124.7	C18—C19—H19	119.9
N1—C1—H1	124.7	C19—C20—O6	124.7 (3)
C1—C2—C3	106.0 (3)	C19—C20—C21	119.7 (3)
C1—C2—C9	126.1 (3)	O6—C20—C21	115.6 (3)
C3—C2—C9	127.9 (3)	C22—C21—C20	120.4 (3)
C4—C3—C8	118.1 (3)	C22—C21—H21	119.8
C4—C3—C2	134.6 (3)	C20—C21—H21	119.8
C8—C3—C2	107.3 (3)	C21—C22—C17	120.0 (3)
C5—C4—C3	118.9 (4)	C21—C22—H22	120.0
C5—C4—H4	120.6	C17—C22—H22	120.0
C3—C4—H4	120.6	O6—C23—H23A	109.5
C4—C5—C6	121.8 (4)	O6—C23—H23B	109.5
C4—C5—H5	119.1	H23A—C23—H23B	109.5
C6—C5—H5	119.1	O6—C23—H23C	109.5
C7—C6—C5	121.1 (4)	H23A—C23—H23C	109.5
C7—C6—H6	119.5	H23B—C23—H23C	109.5
C5—C6—H6	119.5	C25—C24—C29	118.1 (3)
C6—C7—C8	117.7 (3)	C25—C24—C15	121.7 (3)
C6—C7—H7	121.2	C29—C24—C15	120.3 (3)
C8—C7—H7	121.2	C24—C25—C26	121.1 (3)
N1—C8—C7	130.5 (3)	C24—C25—H25	119.4
N1—C8—C3	107.0 (3)	C26—C25—H25	119.4
C7—C8—C3	122.5 (4)	C27—C26—C25	120.4 (4)
C2—C9—C10	112.3 (2)	C27—C26—H26	119.8
C2—C9—H9A	109.1	C25—C26—H26	119.8
C10—C9—H9A	109.1	C26—C27—C28	119.1 (3)
C2—C9—H9B	109.1	C26—C27—H27	120.4
C10—C9—H9B	109.1	C28—C27—H27	120.4
H9A—C9—H9B	107.9	C29—C28—C27	120.3 (3)
N2—C10—C36	108.6 (2)	C29—C28—H28	119.8
N2—C10—C9	109.8 (2)	C27—C28—H28	119.8
C36—C10—C9	110.0 (2)	C28—C29—C24	121.0 (4)
N2—C10—C11	105.2 (2)	C28—C29—H29	119.5
C36—C10—C11	108.7 (2)	C24—C29—H29	119.5
C9—C10—C11	114.2 (2)	C35—C30—C31	117.5 (3)
C30—C11—C12	111.5 (2)	C35—C30—C11	121.3 (3)
C30—C11—C10	117.8 (2)	C31—C30—C11	121.2 (3)
C12—C11—C10	103.5 (2)	C32—C31—C30	121.9 (4)
C30—C11—H11	107.8	C32—C31—H31	119.1
C12—C11—H11	107.8	C30—C31—H31	119.1
C10—C11—H11	107.8	C33—C32—C31	120.2 (5)
N3—C12—C11	113.1 (3)	C33—C32—H32	119.9
N3—C12—C13	106.7 (2)	C31—C32—H32	119.9
C11—C12—C13	103.8 (2)	C32—C33—C34	119.7 (4)
N3—C12—H12	111.0	C32—C33—H33	120.2
C11—C12—H12	111.0	C34—C33—H33	120.2
C13—C12—H12	111.0	C33—C34—C35	120.4 (4)
N2—C13—C14	113.7 (2)	C33—C34—H34	119.8
N2—C13—C12	103.5 (2)	C35—C34—H34	119.8
C14—C13—C12	117.3 (2)	C30—C35—C34	120.3 (4)
N2—C13—H13	107.3	C30—C35—Cl1	122.1 (3)
C14—C13—H13	107.3	C34—C35—Cl1	117.5 (4)
C12—C13—H13	107.3	O1—C36—O2	125.4 (3)
N4—C14—C13	115.3 (3)	O1—C36—C10	123.6 (3)
N4—C14—C15	87.1 (2)	O2—C36—C10	111.0 (3)
C13—C14—C15	117.8 (2)	O2—C37—H37A	109.5
N4—C14—H14	111.5	O2—C37—H37B	109.5
C13—C14—H14	111.5	H37A—C37—H37B	109.5
C15—C14—H14	111.5	O2—C37—H37C	109.5
C24—C15—C16	116.4 (3)	H37A—C37—H37C	109.5
C24—C15—C14	119.7 (3)	H37B—C37—H37C	109.5

N1—C1—C2—C3	0.6 (4)	C16—C15—C24—C29	−150.9 (3)
N1—C1—C2—C9	−178.0 (3)	C14—C15—C24—C29	109.9 (4)
C1—C2—C3—C4	−178.8 (3)	C29—C24—C25—C26	−0.2 (5)
C9—C2—C3—C4	−0.3 (6)	C15—C24—C25—C26	179.1 (3)
C1—C2—C3—C8	−0.5 (4)	C24—C25—C26—C27	−0.3 (6)
C9—C2—C3—C8	178.1 (3)	C25—C26—C27—C28	0.1 (6)
C8—C3—C4—C5	−0.3 (5)	C26—C27—C28—C29	0.6 (6)
C2—C3—C4—C5	177.9 (4)	C27—C28—C29—C24	−1.1 (6)
C3—C4—C5—C6	0.6 (6)	C25—C24—C29—C28	0.9 (6)
C4—C5—C6—C7	0.1 (7)	C15—C24—C29—C28	−178.4 (4)
C5—C6—C7—C8	−1.2 (6)	C12—C11—C30—C35	−138.3 (3)
C6—C7—C8—N1	−178.1 (4)	C10—C11—C30—C35	102.2 (3)
C6—C7—C8—C3	1.5 (5)	C12—C11—C30—C31	39.4 (4)
C4—C3—C8—N1	178.9 (3)	C10—C11—C30—C31	−80.1 (4)
C2—C3—C8—N1	0.2 (3)	C35—C30—C31—C32	−0.5 (5)
C4—C3—C8—C7	−0.7 (5)	C11—C30—C31—C32	−178.3 (3)
C2—C3—C8—C7	−179.4 (3)	C30—C31—C32—C33	−0.7 (6)
C1—C2—C9—C10	−76.9 (4)	C31—C32—C33—C34	0.8 (7)
C3—C2—C9—C10	104.8 (4)	C32—C33—C34—C35	0.3 (7)
C2—C9—C10—N2	58.5 (3)	C31—C30—C35—C34	1.6 (5)
C2—C9—C10—C36	−61.0 (3)	C11—C30—C35—C34	179.4 (3)
C2—C9—C10—C11	176.5 (2)	C31—C30—C35—Cl1	−176.2 (2)
N2—C10—C11—C30	134.8 (3)	C11—C30—C35—Cl1	1.6 (5)
C36—C10—C11—C30	−109.0 (3)	C33—C34—C35—C30	−1.5 (6)
C9—C10—C11—C30	14.2 (4)	C33—C34—C35—Cl1	176.4 (4)
N2—C10—C11—C12	11.2 (3)	N2—C10—C36—O1	16.0 (4)
C36—C10—C11—C12	127.4 (3)	C9—C10—C36—O1	136.2 (3)
C9—C10—C11—C12	−109.4 (3)	C11—C10—C36—O1	−98.0 (3)
C30—C11—C12—N3	131.4 (2)	N2—C10—C36—O2	−165.9 (2)
C10—C11—C12—N3	−101.0 (2)	C9—C10—C36—O2	−45.6 (3)
C30—C11—C12—C13	−113.4 (3)	C11—C10—C36—O2	80.1 (3)
C10—C11—C12—C13	14.3 (3)	C7—C8—N1—C1	179.7 (4)
N3—C12—C13—N2	84.1 (3)	C3—C8—N1—C1	0.1 (4)
C11—C12—C13—N2	−35.6 (3)	C2—C1—N1—C8	−0.4 (4)
N3—C12—C13—C14	−42.0 (3)	C14—C13—N2—C10	172.5 (2)
C11—C12—C13—C14	−161.7 (2)	C12—C13—N2—C10	44.1 (3)
N2—C13—C14—N4	72.2 (3)	C36—C10—N2—C13	−150.8 (2)
C12—C13—C14—N4	−166.9 (2)	C9—C10—N2—C13	88.8 (2)
N2—C13—C14—C15	172.8 (3)	C11—C10—N2—C13	−34.6 (3)
C12—C13—C14—C15	−66.3 (4)	C11—C12—N3—O4	−157.2 (3)
N4—C14—C15—C24	113.5 (3)	C13—C12—N3—O4	89.3 (3)
C13—C14—C15—C24	−3.7 (5)	C11—C12—N3—O3	25.3 (4)
N4—C14—C15—C16	−3.9 (3)	C13—C12—N3—O3	−88.2 (3)
C13—C14—C15—C16	−121.1 (3)	O5—C16—N4—C17	16.9 (7)
C24—C15—C16—O5	63.8 (6)	C15—C16—N4—C17	−163.0 (3)
C14—C15—C16—O5	−175.6 (5)	O5—C16—N4—C14	175.3 (5)
C24—C15—C16—N4	−116.3 (3)	C15—C16—N4—C14	−4.5 (3)
C14—C15—C16—N4	4.2 (3)	C22—C17—N4—C16	−36.5 (5)
C22—C17—C18—C19	2.4 (5)	C18—C17—N4—C16	140.0 (4)
N4—C17—C18—C19	−174.1 (3)	C22—C17—N4—C14	173.4 (3)
C17—C18—C19—C20	0.8 (6)	C18—C17—N4—C14	−10.1 (6)
C18—C19—C20—O6	176.6 (4)	C13—C14—N4—C16	123.8 (3)
C18—C19—C20—C21	−3.5 (6)	C15—C14—N4—C16	4.4 (3)
C19—C20—C21—C22	3.2 (6)	C13—C14—N4—C17	−79.3 (4)
O6—C20—C21—C22	−176.9 (4)	C15—C14—N4—C17	161.3 (4)
C20—C21—C22—C17	−0.1 (7)	O1—C36—O2—C37	−1.3 (5)
C18—C17—C22—C21	−2.7 (6)	C10—C36—O2—C37	−179.4 (3)
N4—C17—C22—C21	173.9 (4)	C19—C20—O6—C23	−4.1 (6)
C16—C15—C24—C25	29.9 (5)	C21—C20—O6—C23	176.0 (4)
C14—C15—C24—C25	−69.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cl1	0.98	2.57	3.095 (4)	114
C11—H11···O3	0.98	2.37	2.786 (4)	105
C22—H22···O5	0.93	2.59	3.080 (6)	113
C14—H14···O4ⁱ	0.98	2.53	3.443 (5)	154
C34—H34···O4ⁱⁱ	0.93	2.59	3.414 (6)	148
N1—H1A···O6ⁱⁱⁱ	0.86	2.14	2.982 (5)	167

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

Experimental details

Crystal data
Chemical formula	C₃₇H₃₃ClN₄O₆
M_r	665.12
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.399 (3), 12.500 (3), 14.211 (3)
α, β, γ (°)	93.766 (6), 99.962 (6), 114.066 (5)
V (Å³)	1642.1 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.30 × 0.20 × 0.16

Data collection
Diffractometer	Bruker KAPPA APEX2 CCD diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.951, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	25481, 5563, 3770
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.317, 1.10
No. of reflections	5563
No. of parameters	433
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.64

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), 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
C11—H11···Cl1	0.98	2.57	3.095 (4)	114
C11—H11···O3	0.98	2.37	2.786 (4)	105
C22—H22···O5	0.93	2.59	3.080 (6)	113
C14—H14···O4ⁱ	0.98	2.53	3.443 (5)	154
C34—H34···O4ⁱⁱ	0.93	2.59	3.414 (6)	148
N1—H1A···O6ⁱⁱⁱ	0.86	2.14	2.982 (5)	167

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

Acknowledgements

SN thanks Professor M. N. Ponnuswamy, Department of Crystallography and Biophysics, University of Madras, India, for his guidance and valuable suggestions. SN thanks SRM management, India, for their support.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Bhaskaran, S., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Arumugam, N. & Raghunathan, R. (2006). Anal. Sci. 22, x57–x58. CAS Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Bruggink, A. (2001). Synthesis of β-Lactam Antibiotics, Chemistry, Biocatalysis and Process Integration, edited by A. Bruggink. Dordrecht: Kluwer. Google Scholar
Bruker (2004). APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cha, J. M., Yang, S. & Carlson, K. H. (2006). J. Chromatogr. A, 1115, 46–57. Web of Science CrossRef PubMed CAS Google Scholar
Coyne, A. G., Muller-Bunz, H. & Guiry, P. J. (2007). Tetrahedron Asymmetry, 18, 199–207. Web of Science CSD CrossRef CAS Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Dobrowolski, J. C., Sadlej, J. & Mazurek, A. P. (2004). J. Mol. Struct. THEOCHEM, 684, 181–186. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Georg, G. I. (1993). The Organic Chemistry of β-Lactams, edited by G. I. Georg. New York: VCH. Google Scholar
Kamala, E. T. S., Nirmala, S., Sudha, L., Arumugam, N. & Raghunathan, R. (2008). Acta Cryst. E64, o716–o717. Web of Science CSD CrossRef IUCr Journals Google Scholar
Katritzky, A. R., Rees, C. W. & Scriven, E. F. V. (1996). Comprehensive Heterocyclic Chemistry II, edited by A. R. Katritzky, C. W. Rees & E. F. V. Scriven, Vol. 1b, chs. 1.18–1.20. New York: Elsevier. Google Scholar
Morin, M. B. & Gorman, M. (1982). Chemistry and Biology of β-Lactam Antibiotics, edited by M. B. Morin & M. Gorman, pp. 1– 3. New York: Academic Press. Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. 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. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ülkü, D., Ercan, F. & Güner, V. (1997). Acta Cryst. C53, 1945–1947. Web of Science CSD CrossRef IUCr Journals Google Scholar

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages o1070-o1071

doi:10.1107/S1600536808013585

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

Methyl 3-(2-chloro­phenyl)-2-(1H-indol-3-ylmethyl)-5-[1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-4-nitropyr­rolidine-2-carboxylate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 3-(2-chlorophenyl)-2-(1H-indol-3-ylmethyl)-5-[1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-4-nitropyrrolidine-2-carboxylate