Methyl 11-hy­droxy-9-[1-(4-meth­oxy­phen­yl)-4-oxo-3-phen­oxy­azetidin-2-yl]-18-oxo-10-oxa-2-aza­penta­cyclo­[9.7.0.01,8.02,6.012,17]octa­deca-12(17),13,15-triene-8-carboxyl­ate

Sundaramoorthy, S.; Rajesh, R.; Raghunathan, R.; Velmurugan, D.

doi:10.1107/S1600536812027341

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages o2200-o2201

https://doi.org/10.1107/S1600536812027341

Open

access

Methyl 11-hydroxy-9-[1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin-2-yl]-18-oxo-10-oxa-2-azapentacyclo[9.7.0.0^1,8.0^2,6.0^12,17]octadeca-12(17),13,15-triene-8-carboxylate

S. Sundaramoorthy,^a R. Rajesh,^b R. Raghunathan ^b and D. Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: shirai2011@gmail.com

(Received 9 June 2012; accepted 16 June 2012; online 23 June 2012)

In the title compound, C₃₄H₃₂N₂O₈, one of the pyrrolidine rings in the pyrrolizidine ring system adopts a twist conformation, whereas the other ring adopts an envelope conformation (C atom as flap). The five-membered ring in the indene ring system and the fused furan ring also adopt envelope conformations (C and O atoms as flaps, respectively). The β-lactam ring makes dihedral angles of 23.41 (2) and 25.98 (2)°, respectively, with the attached methoxyphenyl and phenoxy rings. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond, generating an S(5) motif. In the crystal, molecules are linked into C(12) chains running along the a axis by C—H⋯O hydrogen bonds. The structure is further consolidated by weak intermolecular C—H⋯π and π–π interactions [centroid–centroid distance = 3.7987 (14) Å].

Related literature

For general background to β-lactams, see: Banik & Becker (2000 ); Brakhage (1998 ). For a related structure, see: Arun et al. (2003 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₃₄H₃₂N₂O₈
M_r = 596.62
Monoclinic, P 2₁ /c
a = 11.4251 (13) Å
b = 7.8362 (8) Å
c = 32.041 (4) Å
β = 91.313 (8)°
V = 2867.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.2 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.976, T_max = 0.980
27667 measured reflections
7104 independent reflections
3251 reflections with I > 2σ(I)
R_int = 0.083

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.141
S = 0.99
7104 reflections
400 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg7 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯N2	0.82	2.10	2.638 (2)	122
C15—H15⋯O6ⁱ	0.93	2.56	3.231 (3)	129
C12—H12⋯Cg7ⁱⁱ	0.93	2.95	3.775 (3)	149
Symmetry codes: (i) x-1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812027341/pv2560sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027341/pv2560Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812027341/pv2560Isup3.cml

checkCIF report

Comment top

The role of β-lactam antibiotics is well known (Banik & Becker, 2000). The most commonly used β-lactam antibiotics for the therapy of infectious diseases are penicillin and cephalosporin (Brakhage, 1998). In view of potential applications, the crystal structure determination of the title β-lactam derivative was carried out which is reported in this article.

In the title compound (Fig. 1), the β-lactam ring makes dihedral angle of 31.36 (1)° with the indene ring system. The maximum deviation of indene ring system is 0.212 (2) Å for atom C19. The β-lactam ring makes dihedral angles 23.41 (15) and 25.98 (15)°, respectively, with the attached methoxyphenyl and phenoxy rings. The carboxylate group adopts an extended conformation with thetorsion angle C18—C33—O8—C34 = 171.9 (2)°. The five-membered ring (C19/C20/C21/C26/C27) in the inden ring system and the fused furan ring (O4/C17—C20) adopt envelope conformations, with C19 and O4 atoms deviating by 0.135 (2) and -0.221 (2) Å, respectively, from the planes formed by the remaining atoms of the rings. In the pyrrolizidine ring system, the pyrrolidine ring (C18/C19/N2/C31/C32) adopts a C31-envelope conformation, with C31 deviating by 0.216 (2) Å from the remaining ring atoms. The bond lengths and bond angles in the title compound agree with the corresponding bond lengths and angles reported for a closely related compound (Arun et al., (2003).

The molecular structure of the title compound is stabilized by a strong O5—H5A···N2 hydrogen bond, generating an S(5) motif (Bernstein et al., 1995). The H-atom bonded to C15 is involved in hydrogen bonding with atom O6 forming a C(12) chain running along the a axis (Tab. 1 & Fig. 2). A weak intermolecular C—H···π interaction involving the C12—H12 group and the C1—C16 phenoxy ring is also observed.

Related literature top

For general background to β-lactams, see: Banik & Becker (2000); Brakhage (1998). For a related structure, see: Arun et al. (2003). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

To a reaction mixture of 2-(hydroxy(1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin -2-yl)methyl)acrylate (1 mmol), ninhydrine (1.1 mmol) and proline (1.1 mmol) were refluxed in methanol until completion of the reaction was evidenced by TLC analysis. After completion of the reaction the solvent was evaporated under reduced pressure. The crude reaction mixture was dissolved in dichloromethane and washed with water followed by brine solution. The organic layer was separated and dried over sodium sulfate. Filtering and evaporation of the organic solvent under reduced pressure were carried out. The product was separated by column chromatography using hexane and ethyl acetate (3: 7) as an eluent to give colorless solid. The product was dissolved in chloroform and heated for two minutes. The resulting solution was subjected to crystallization by slow evaporation of the solvent resulting in single crystals of the title compound suitable for XRD studies.

Structure description top

For general background to β-lactams, see: Banik & Becker (2000); Brakhage (1998). For a related structure, see: Arun et al. (2003). For hydrogen-bond motifs, see: Bernstein et al. (1995).

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, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A perspective view of the molecule showing the thermal ellipsoids drawn at the 30% probability level.
	Fig. 2. C—H···O and O—H···N interactions (dotted lines) in the crystal structure of the title compound viewed down the b axis.

Methyl 11-hydroxy-9-[1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin-2-yl]-18-oxo- 10-oxa-2-azapentacyclo[9.7.0.0^1,8.0^2,6.0^12,17]octadeca-12(17),13,15- triene-8-carboxylate top

Crystal data top

C₃₄H₃₂N₂O₈	F(000) = 1256
M_r = 596.62	D_x = 1.382 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1035 reflections
a = 11.4251 (13) Å	θ = 1.3–28.3°
b = 7.8362 (8) Å	µ = 0.10 mm⁻¹
c = 32.041 (4) Å	T = 293 K
β = 91.313 (8)°	Block, colourless
V = 2867.9 (6) Å³	0.25 × 0.22 × 0.2 mm
Z = 4

Data collection top

Bruker SMART APEXII area-detector diffractometer	7104 independent reflections
Radiation source: fine-focus sealed tube	3251 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.083
ω and φ scans	θ_max = 28.3°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
T_min = 0.976, T_max = 0.980	k = −10→10
27667 measured reflections	l = −42→42

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0537P)²] where P = (F_o² + 2F_c²)/3
7104 reflections	(Δ/σ)_max < 0.001
400 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₃₄H₃₂N₂O₈	V = 2867.9 (6) Å³
M_r = 596.62	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.4251 (13) Å	µ = 0.10 mm⁻¹
b = 7.8362 (8) Å	T = 293 K
c = 32.041 (4) Å	0.25 × 0.22 × 0.2 mm
β = 91.313 (8)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	7104 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3251 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.980	R_int = 0.083
27667 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 0.99	Δρ_max = 0.26 e Å⁻³
7104 reflections	Δρ_min = −0.20 e Å⁻³
400 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
C1	0.5692 (2)	0.7918 (3)	0.02316 (7)	0.0411 (6)
C2	0.4969 (2)	0.7168 (3)	−0.00647 (7)	0.0494 (6)
H2	0.4337	0.6513	0.0018	0.059*
C3	0.5175 (2)	0.7380 (3)	−0.04839 (8)	0.0523 (7)
H3	0.4682	0.6878	−0.0683	0.063*
C4	0.6120 (2)	0.8343 (3)	−0.06043 (7)	0.0484 (6)
C5	0.6846 (2)	0.9091 (3)	−0.03100 (7)	0.0513 (7)
H5	0.7482	0.9738	−0.0394	0.062*
C6	0.6638 (2)	0.8886 (3)	0.01066 (7)	0.0469 (6)
H6	0.7130	0.9396	0.0305	0.056*
C7	0.5862 (3)	0.7665 (4)	−0.13225 (9)	0.0926 (11)
H7A	0.5981	0.6474	−0.1266	0.139*
H7B	0.6184	0.7943	−0.1588	0.139*
H7C	0.5038	0.7911	−0.1328	0.139*
C8	0.6332 (2)	0.7868 (3)	0.10200 (7)	0.0416 (6)
H8	0.6557	0.9058	0.1071	0.050*
C9	0.53063 (19)	0.7311 (3)	0.12942 (7)	0.0420 (6)
H9	0.5417	0.6144	0.1397	0.050*
C10	0.4546 (2)	0.7338 (3)	0.08915 (8)	0.0478 (6)
C11	0.4395 (2)	0.7776 (3)	0.19371 (7)	0.0412 (6)
C12	0.4698 (2)	0.8218 (3)	0.23396 (8)	0.0511 (6)
H12	0.5336	0.8928	0.2394	0.061*
C13	0.4048 (2)	0.7598 (3)	0.26613 (8)	0.0564 (7)
H13	0.4247	0.7892	0.2935	0.068*
C14	0.3106 (2)	0.6547 (3)	0.25828 (8)	0.0563 (7)
H14	0.2671	0.6127	0.2802	0.068*
C15	0.2813 (2)	0.6123 (3)	0.21807 (8)	0.0542 (7)
H15	0.2174	0.5412	0.2127	0.065*
C16	0.3446 (2)	0.6730 (3)	0.18552 (7)	0.0478 (6)
H16	0.3239	0.6441	0.1582	0.057*
C17	0.73901 (19)	0.6701 (3)	0.10020 (7)	0.0381 (5)
H17	0.7718	0.6788	0.0723	0.046*
C18	0.83833 (19)	0.7027 (3)	0.13279 (6)	0.0355 (5)
C19	0.88557 (19)	0.5159 (3)	0.14320 (6)	0.0376 (5)
C20	0.8029 (2)	0.3992 (3)	0.11556 (7)	0.0403 (6)
C21	0.8728 (2)	0.3585 (3)	0.07798 (7)	0.0412 (6)
C22	0.8357 (2)	0.2882 (3)	0.04033 (8)	0.0530 (7)
H22	0.7571	0.2629	0.0352	0.064*
C23	0.9177 (3)	0.2571 (3)	0.01084 (8)	0.0632 (8)
H23	0.8940	0.2103	−0.0147	0.076*
C24	1.0348 (3)	0.2935 (4)	0.01796 (8)	0.0647 (8)
H24	1.0885	0.2691	−0.0026	0.078*
C25	1.0732 (2)	0.3655 (3)	0.05511 (8)	0.0552 (7)
H25	1.1518	0.3913	0.0600	0.066*
C26	0.9898 (2)	0.3977 (3)	0.08485 (7)	0.0428 (6)
C27	1.0082 (2)	0.4737 (3)	0.12642 (7)	0.0446 (6)
C28	0.9643 (2)	0.5013 (4)	0.21783 (7)	0.0655 (8)
H28A	1.0137	0.4006	0.2184	0.079*
H28B	1.0118	0.6001	0.2114	0.079*
C29	0.9052 (3)	0.5235 (4)	0.25785 (8)	0.0727 (9)
H29A	0.9546	0.5866	0.2774	0.087*
H29B	0.8869	0.4135	0.2700	0.087*
C30	0.7948 (2)	0.6211 (4)	0.24787 (7)	0.0576 (7)
H30A	0.8036	0.7400	0.2558	0.069*
H30B	0.7293	0.5730	0.2626	0.069*
C31	0.7756 (2)	0.6046 (3)	0.20060 (6)	0.0432 (6)
H31	0.6970	0.5608	0.1941	0.052*
C32	0.7991 (2)	0.7655 (3)	0.17556 (6)	0.0424 (6)
H32A	0.8600	0.8335	0.1891	0.051*
H32B	0.7287	0.8341	0.1727	0.051*
C33	0.9311 (2)	0.8179 (3)	0.11405 (7)	0.0413 (6)
C34	1.1133 (2)	0.9561 (4)	0.12607 (8)	0.0693 (8)
H34A	1.1559	0.8824	0.1079	0.104*
H34B	1.1632	0.9908	0.1490	0.104*
H34C	1.0873	1.0551	0.1108	0.104*
N1	0.55049 (16)	0.7704 (3)	0.06619 (6)	0.0451 (5)
N2	0.86574 (17)	0.4818 (2)	0.18691 (5)	0.0433 (5)
O1	0.64164 (18)	0.8632 (2)	−0.10114 (5)	0.0725 (6)
O2	0.35322 (16)	0.7067 (2)	0.07968 (5)	0.0623 (5)
O3	0.50681 (14)	0.8443 (2)	0.16232 (5)	0.0511 (4)
O4	0.70046 (13)	0.49763 (19)	0.10630 (4)	0.0429 (4)
O5	0.76948 (16)	0.2530 (2)	0.13645 (5)	0.0549 (5)
H5A	0.7789	0.2671	0.1617	0.082*
O6	1.10093 (16)	0.4957 (3)	0.14436 (5)	0.0694 (6)
O7	0.93303 (17)	0.8573 (3)	0.07831 (5)	0.0721 (6)
O8	1.01251 (15)	0.8656 (2)	0.14184 (5)	0.0608 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0358 (14)	0.0458 (14)	0.0416 (14)	0.0071 (11)	−0.0018 (11)	0.0055 (11)
C2	0.0393 (15)	0.0575 (16)	0.0512 (15)	−0.0035 (12)	−0.0038 (12)	0.0050 (12)
C3	0.0522 (18)	0.0579 (17)	0.0462 (15)	−0.0057 (13)	−0.0102 (13)	−0.0054 (12)
C4	0.0559 (18)	0.0500 (15)	0.0392 (14)	0.0028 (13)	0.0005 (12)	0.0003 (11)
C5	0.0516 (17)	0.0559 (16)	0.0464 (15)	−0.0085 (13)	0.0000 (13)	0.0057 (12)
C6	0.0455 (16)	0.0530 (16)	0.0419 (14)	−0.0050 (12)	−0.0043 (12)	0.0017 (12)
C7	0.129 (3)	0.099 (3)	0.0503 (18)	−0.027 (2)	−0.0015 (19)	−0.0174 (17)
C8	0.0378 (14)	0.0492 (15)	0.0378 (12)	0.0021 (11)	0.0012 (11)	0.0019 (11)
C9	0.0383 (15)	0.0469 (14)	0.0410 (13)	0.0012 (11)	0.0075 (11)	0.0005 (11)
C10	0.0393 (17)	0.0534 (16)	0.0508 (15)	0.0046 (12)	0.0038 (13)	0.0019 (12)
C11	0.0358 (15)	0.0427 (14)	0.0455 (14)	0.0051 (11)	0.0087 (11)	0.0009 (11)
C12	0.0457 (16)	0.0552 (16)	0.0524 (16)	−0.0035 (12)	−0.0003 (13)	−0.0113 (13)
C13	0.065 (2)	0.0616 (18)	0.0421 (15)	0.0095 (15)	−0.0004 (14)	−0.0056 (13)
C14	0.0593 (19)	0.0568 (17)	0.0535 (17)	0.0075 (14)	0.0157 (14)	0.0056 (13)
C15	0.0406 (16)	0.0626 (18)	0.0599 (17)	−0.0058 (13)	0.0073 (13)	−0.0004 (14)
C16	0.0370 (15)	0.0630 (16)	0.0434 (14)	0.0010 (12)	−0.0007 (12)	−0.0036 (12)
C17	0.0344 (14)	0.0468 (14)	0.0331 (12)	0.0000 (11)	0.0019 (10)	−0.0011 (10)
C18	0.0333 (13)	0.0406 (13)	0.0327 (11)	−0.0010 (10)	0.0012 (10)	−0.0024 (10)
C19	0.0360 (14)	0.0441 (14)	0.0327 (12)	0.0005 (10)	0.0012 (10)	−0.0017 (10)
C20	0.0357 (14)	0.0424 (14)	0.0428 (13)	−0.0022 (11)	−0.0003 (11)	−0.0013 (11)
C21	0.0464 (16)	0.0374 (13)	0.0399 (13)	0.0038 (11)	0.0027 (11)	−0.0030 (10)
C22	0.0586 (18)	0.0508 (16)	0.0494 (15)	0.0017 (13)	−0.0016 (14)	−0.0113 (12)
C23	0.072 (2)	0.070 (2)	0.0471 (16)	0.0051 (16)	−0.0005 (15)	−0.0192 (13)
C24	0.069 (2)	0.078 (2)	0.0472 (16)	0.0126 (16)	0.0133 (15)	−0.0088 (14)
C25	0.0470 (17)	0.0676 (18)	0.0515 (16)	0.0088 (13)	0.0082 (13)	−0.0012 (13)
C26	0.0430 (16)	0.0470 (15)	0.0385 (13)	0.0078 (11)	0.0036 (11)	−0.0010 (11)
C27	0.0363 (15)	0.0523 (15)	0.0451 (14)	0.0018 (11)	−0.0019 (12)	−0.0011 (11)
C28	0.0622 (19)	0.092 (2)	0.0416 (15)	0.0089 (16)	−0.0119 (13)	0.0089 (15)
C29	0.096 (3)	0.078 (2)	0.0435 (16)	−0.0044 (18)	−0.0176 (15)	−0.0007 (14)
C30	0.063 (2)	0.0757 (19)	0.0339 (13)	−0.0116 (15)	0.0076 (12)	−0.0020 (13)
C31	0.0398 (15)	0.0565 (15)	0.0334 (12)	−0.0062 (12)	0.0045 (11)	−0.0040 (11)
C32	0.0431 (15)	0.0503 (15)	0.0340 (12)	−0.0014 (11)	0.0034 (10)	−0.0055 (10)
C33	0.0427 (15)	0.0446 (14)	0.0364 (13)	−0.0013 (11)	0.0007 (11)	−0.0020 (11)
C34	0.0558 (19)	0.088 (2)	0.0643 (18)	−0.0359 (16)	0.0021 (14)	0.0101 (16)
N1	0.0325 (12)	0.0625 (14)	0.0403 (11)	0.0034 (9)	−0.0006 (9)	0.0083 (9)
N2	0.0451 (13)	0.0527 (12)	0.0320 (10)	0.0002 (10)	−0.0013 (9)	0.0025 (9)
O1	0.0945 (16)	0.0825 (14)	0.0404 (10)	−0.0238 (11)	0.0005 (10)	−0.0019 (9)
O2	0.0365 (12)	0.0868 (14)	0.0636 (12)	−0.0041 (10)	0.0012 (9)	0.0034 (10)
O3	0.0526 (11)	0.0489 (10)	0.0525 (10)	−0.0027 (8)	0.0174 (9)	−0.0059 (8)
O4	0.0334 (9)	0.0449 (10)	0.0502 (9)	−0.0012 (7)	−0.0027 (7)	−0.0069 (8)
O5	0.0636 (12)	0.0470 (11)	0.0543 (10)	−0.0104 (9)	0.0041 (10)	0.0032 (8)
O6	0.0409 (12)	0.1050 (16)	0.0618 (12)	0.0020 (11)	−0.0062 (9)	−0.0172 (11)
O7	0.0787 (15)	0.0973 (15)	0.0402 (11)	−0.0351 (11)	−0.0028 (9)	0.0131 (10)
O8	0.0526 (12)	0.0825 (13)	0.0471 (10)	−0.0282 (10)	−0.0061 (9)	0.0101 (9)

Geometric parameters (Å, º) top

C1—C2	1.376 (3)	C18—C19	1.593 (3)
C1—C6	1.387 (3)	C19—N2	1.449 (3)
C1—N1	1.410 (3)	C19—C27	1.547 (3)
C2—C3	1.379 (3)	C19—C20	1.572 (3)
C2—H2	0.9300	C20—O5	1.385 (3)
C3—C4	1.379 (3)	C20—O4	1.427 (3)
C3—H3	0.9300	C20—C21	1.495 (3)
C4—C5	1.373 (3)	C21—C26	1.384 (3)
C4—O1	1.374 (3)	C21—C22	1.384 (3)
C5—C6	1.371 (3)	C22—C23	1.368 (3)
C5—H5	0.9300	C22—H22	0.9300
C6—H6	0.9300	C23—C24	1.381 (4)
C7—O1	1.393 (3)	C23—H23	0.9300
C7—H7A	0.9600	C24—C25	1.380 (3)
C7—H7B	0.9600	C24—H24	0.9300
C7—H7C	0.9600	C25—C26	1.386 (3)
C8—N1	1.475 (3)	C25—H25	0.9300
C8—C17	1.518 (3)	C26—C27	1.469 (3)
C8—C9	1.543 (3)	C27—O6	1.206 (3)
C8—H8	0.9800	C28—C29	1.474 (4)
C9—O3	1.409 (3)	C28—N2	1.491 (3)
C9—C10	1.539 (3)	C28—H28A	0.9700
C9—H9	0.9800	C28—H28B	0.9700
C10—O2	1.209 (3)	C29—C30	1.503 (4)
C10—N1	1.364 (3)	C29—H29A	0.9700
C11—C12	1.372 (3)	C29—H29B	0.9700
C11—C16	1.379 (3)	C30—C31	1.531 (3)
C11—O3	1.383 (3)	C30—H30A	0.9700
C12—C13	1.373 (3)	C30—H30B	0.9700
C12—H12	0.9300	C31—N2	1.483 (3)
C13—C14	1.374 (3)	C31—C32	1.521 (3)
C13—H13	0.9300	C31—H31	0.9800
C14—C15	1.365 (3)	C32—H32A	0.9700
C14—H14	0.9300	C32—H32B	0.9700
C15—C16	1.368 (3)	C33—O7	1.186 (2)
C15—H15	0.9300	C33—O8	1.327 (3)
C16—H16	0.9300	C34—O8	1.453 (3)
C17—O4	1.436 (3)	C34—H34A	0.9600
C17—C18	1.546 (3)	C34—H34B	0.9600
C17—H17	0.9800	C34—H34C	0.9600
C18—C33	1.526 (3)	O5—H5A	0.8200
C18—C32	1.533 (3)

C2—C1—C6	119.6 (2)	O5—C20—C21	111.76 (19)
C2—C1—N1	121.4 (2)	O4—C20—C21	113.51 (18)
C6—C1—N1	119.0 (2)	O5—C20—C19	112.18 (17)
C1—C2—C3	120.5 (2)	O4—C20—C19	106.39 (17)
C1—C2—H2	119.8	C21—C20—C19	104.65 (18)
C3—C2—H2	119.8	C26—C21—C22	120.2 (2)
C2—C3—C4	119.4 (2)	C26—C21—C20	110.86 (19)
C2—C3—H3	120.3	C22—C21—C20	128.9 (2)
C4—C3—H3	120.3	C23—C22—C21	118.2 (3)
C5—C4—O1	115.1 (2)	C23—C22—H22	120.9
C5—C4—C3	120.4 (2)	C21—C22—H22	120.9
O1—C4—C3	124.6 (2)	C22—C23—C24	121.7 (2)
C6—C5—C4	120.2 (2)	C22—C23—H23	119.2
C6—C5—H5	119.9	C24—C23—H23	119.2
C4—C5—H5	119.9	C25—C24—C23	121.0 (3)
C5—C6—C1	120.0 (2)	C25—C24—H24	119.5
C5—C6—H6	120.0	C23—C24—H24	119.5
C1—C6—H6	120.0	C24—C25—C26	117.2 (3)
O1—C7—H7A	109.5	C24—C25—H25	121.4
O1—C7—H7B	109.5	C26—C25—H25	121.4
H7A—C7—H7B	109.5	C21—C26—C25	121.8 (2)
O1—C7—H7C	109.5	C21—C26—C27	110.6 (2)
H7A—C7—H7C	109.5	C25—C26—C27	127.6 (2)
H7B—C7—H7C	109.5	O6—C27—C26	126.5 (2)
N1—C8—C17	114.50 (18)	O6—C27—C19	126.6 (2)
N1—C8—C9	86.40 (17)	C26—C27—C19	106.85 (19)
C17—C8—C9	117.85 (19)	C29—C28—N2	103.6 (2)
N1—C8—H8	111.9	C29—C28—H28A	111.0
C17—C8—H8	111.9	N2—C28—H28A	111.0
C9—C8—H8	111.9	C29—C28—H28B	111.0
O3—C9—C10	120.2 (2)	N2—C28—H28B	111.0
O3—C9—C8	114.22 (19)	H28A—C28—H28B	109.0
C10—C9—C8	86.58 (17)	C28—C29—C30	105.9 (2)
O3—C9—H9	111.2	C28—C29—H29A	110.6
C10—C9—H9	111.2	C30—C29—H29A	110.6
C8—C9—H9	111.2	C28—C29—H29B	110.6
O2—C10—N1	132.7 (2)	C30—C29—H29B	110.6
O2—C10—C9	136.7 (2)	H29A—C29—H29B	108.7
N1—C10—C9	90.6 (2)	C29—C30—C31	105.5 (2)
C12—C11—C16	120.6 (2)	C29—C30—H30A	110.6
C12—C11—O3	117.1 (2)	C31—C30—H30A	110.6
C16—C11—O3	122.3 (2)	C29—C30—H30B	110.6
C11—C12—C13	119.1 (2)	C31—C30—H30B	110.6
C11—C12—H12	120.4	H30A—C30—H30B	108.8
C13—C12—H12	120.4	N2—C31—C32	104.47 (18)
C12—C13—C14	120.6 (2)	N2—C31—C30	105.24 (19)
C12—C13—H13	119.7	C32—C31—C30	115.39 (19)
C14—C13—H13	119.7	N2—C31—H31	110.5
C15—C14—C13	119.6 (2)	C32—C31—H31	110.5
C15—C14—H14	120.2	C30—C31—H31	110.5
C13—C14—H14	120.2	C31—C32—C18	105.32 (17)
C14—C15—C16	120.8 (3)	C31—C32—H32A	110.7
C14—C15—H15	119.6	C18—C32—H32A	110.7
C16—C15—H15	119.6	C31—C32—H32B	110.7
C15—C16—C11	119.3 (2)	C18—C32—H32B	110.7
C15—C16—H16	120.4	H32A—C32—H32B	108.8
C11—C16—H16	120.4	O7—C33—O8	123.1 (2)
O4—C17—C8	108.33 (18)	O7—C33—C18	124.2 (2)
O4—C17—C18	106.63 (16)	O8—C33—C18	112.65 (19)
C8—C17—C18	116.62 (18)	O8—C34—H34A	109.5
O4—C17—H17	108.3	O8—C34—H34B	109.5
C8—C17—H17	108.3	H34A—C34—H34B	109.5
C18—C17—H17	108.3	O8—C34—H34C	109.5
C33—C18—C32	112.46 (18)	H34A—C34—H34C	109.5
C33—C18—C17	109.74 (17)	H34B—C34—H34C	109.5
C32—C18—C17	115.58 (18)	C10—N1—C1	134.0 (2)
C33—C18—C19	113.03 (18)	C10—N1—C8	96.14 (18)
C32—C18—C19	102.27 (16)	C1—N1—C8	129.89 (19)
C17—C18—C19	103.27 (16)	C19—N2—C31	106.95 (16)
N2—C19—C27	117.35 (18)	C19—N2—C28	119.41 (18)
N2—C19—C20	109.40 (17)	C31—N2—C28	104.83 (18)
C27—C19—C20	102.52 (17)	C4—O1—C7	118.1 (2)
N2—C19—C18	108.18 (17)	C11—O3—C9	115.24 (17)
C27—C19—C18	115.38 (18)	C20—O4—C17	106.50 (16)
C20—C19—C18	102.71 (16)	C20—O5—H5A	109.5
O5—C20—O4	108.25 (18)	C33—O8—C34	116.94 (19)

C6—C1—C2—C3	−0.3 (4)	C22—C21—C26—C27	178.8 (2)
N1—C1—C2—C3	−179.3 (2)	C20—C21—C26—C27	−2.2 (3)
C1—C2—C3—C4	0.5 (4)	C24—C25—C26—C21	0.5 (4)
C2—C3—C4—C5	−0.3 (4)	C24—C25—C26—C27	−179.7 (2)
C2—C3—C4—O1	179.5 (2)	C21—C26—C27—O6	167.0 (2)
O1—C4—C5—C6	−179.8 (2)	C25—C26—C27—O6	−12.8 (4)
C3—C4—C5—C6	0.0 (4)	C21—C26—C27—C19	−11.7 (3)
C4—C5—C6—C1	0.2 (4)	C25—C26—C27—C19	168.5 (2)
C2—C1—C6—C5	0.0 (4)	N2—C19—C27—O6	−39.2 (3)
N1—C1—C6—C5	179.1 (2)	C20—C19—C27—O6	−159.0 (2)
N1—C8—C9—O3	−125.71 (19)	C18—C19—C27—O6	90.2 (3)
C17—C8—C9—O3	118.4 (2)	N2—C19—C27—C26	139.48 (19)
N1—C8—C9—C10	−3.95 (16)	C20—C19—C27—C26	19.6 (2)
C17—C8—C9—C10	−119.8 (2)	C18—C19—C27—C26	−91.2 (2)
O3—C9—C10—O2	−63.1 (4)	N2—C28—C29—C30	−34.4 (3)
C8—C9—C10—O2	−179.2 (3)	C28—C29—C30—C31	16.9 (3)
O3—C9—C10—N1	120.4 (2)	C29—C30—C31—N2	7.0 (3)
C8—C9—C10—N1	4.26 (18)	C29—C30—C31—C32	−107.5 (2)
C16—C11—C12—C13	0.4 (4)	N2—C31—C32—C18	35.7 (2)
O3—C11—C12—C13	179.4 (2)	C30—C31—C32—C18	150.7 (2)
C11—C12—C13—C14	0.1 (4)	C33—C18—C32—C31	−144.90 (19)
C12—C13—C14—C15	−0.3 (4)	C17—C18—C32—C31	88.0 (2)
C13—C14—C15—C16	0.1 (4)	C19—C18—C32—C31	−23.4 (2)
C14—C15—C16—C11	0.3 (4)	C32—C18—C33—O7	−139.0 (2)
C12—C11—C16—C15	−0.6 (4)	C17—C18—C33—O7	−8.9 (3)
O3—C11—C16—C15	−179.6 (2)	C19—C18—C33—O7	105.8 (3)
N1—C8—C17—O4	−69.7 (2)	C32—C18—C33—O8	43.1 (3)
C9—C8—C17—O4	29.6 (3)	C17—C18—C33—O8	173.25 (19)
N1—C8—C17—C18	170.06 (18)	C19—C18—C33—O8	−72.1 (2)
C9—C8—C17—C18	−90.6 (2)	O2—C10—N1—C1	0.4 (5)
O4—C17—C18—C33	144.22 (17)	C9—C10—N1—C1	177.1 (2)
C8—C17—C18—C33	−94.7 (2)	O2—C10—N1—C8	178.8 (3)
O4—C17—C18—C32	−87.3 (2)	C9—C10—N1—C8	−4.47 (19)
C8—C17—C18—C32	33.8 (3)	C2—C1—N1—C10	−25.0 (4)
O4—C17—C18—C19	23.5 (2)	C6—C1—N1—C10	156.0 (3)
C8—C17—C18—C19	144.57 (18)	C2—C1—N1—C8	157.1 (2)
C33—C18—C19—N2	124.31 (19)	C6—C1—N1—C8	−21.9 (3)
C32—C18—C19—N2	3.2 (2)	C17—C8—N1—C10	123.5 (2)
C17—C18—C19—N2	−117.18 (18)	C9—C8—N1—C10	4.47 (19)
C33—C18—C19—C27	−9.4 (2)	C17—C8—N1—C1	−58.0 (3)
C32—C18—C19—C27	−130.54 (19)	C9—C8—N1—C1	−177.0 (2)
C17—C18—C19—C27	109.1 (2)	C27—C19—N2—C31	151.62 (19)
C33—C18—C19—C20	−120.06 (19)	C20—C19—N2—C31	−92.2 (2)
C32—C18—C19—C20	118.79 (17)	C18—C19—N2—C31	18.9 (2)
C17—C18—C19—C20	−1.6 (2)	C27—C19—N2—C28	33.0 (3)
N2—C19—C20—O5	−24.3 (3)	C20—C19—N2—C28	149.1 (2)
C27—C19—C20—O5	100.9 (2)	C18—C19—N2—C28	−99.7 (2)
C18—C19—C20—O5	−139.07 (18)	C32—C31—N2—C19	−33.9 (2)
N2—C19—C20—O4	93.87 (19)	C30—C31—N2—C19	−155.86 (18)
C27—C19—C20—O4	−140.89 (17)	C32—C31—N2—C28	93.8 (2)
C18—C19—C20—O4	−20.9 (2)	C30—C31—N2—C28	−28.1 (2)
N2—C19—C20—C21	−145.69 (18)	C29—C28—N2—C19	158.7 (2)
C27—C19—C20—C21	−20.4 (2)	C29—C28—N2—C31	39.0 (3)
C18—C19—C20—C21	99.57 (19)	C5—C4—O1—C7	168.1 (3)
O5—C20—C21—C26	−106.8 (2)	C3—C4—O1—C7	−11.7 (4)
O4—C20—C21—C26	130.4 (2)	C12—C11—O3—C9	140.2 (2)
C19—C20—C21—C26	14.8 (2)	C16—C11—O3—C9	−40.7 (3)
O5—C20—C21—C22	72.0 (3)	C10—C9—O3—C11	96.4 (2)
O4—C20—C21—C22	−50.8 (3)	C8—C9—O3—C11	−162.82 (18)
C19—C20—C21—C22	−166.4 (2)	O5—C20—O4—C17	157.98 (16)
C26—C21—C22—C23	1.0 (4)	C21—C20—O4—C17	−77.3 (2)
C20—C21—C22—C23	−177.8 (2)	C19—C20—O4—C17	37.2 (2)
C21—C22—C23—C24	0.2 (4)	C8—C17—O4—C20	−164.82 (16)
C22—C23—C24—C25	−1.0 (4)	C18—C17—O4—C20	−38.6 (2)
C23—C24—C25—C26	0.6 (4)	O7—C33—O8—C34	−6.0 (4)
C22—C21—C26—C25	−1.3 (4)	C18—C33—O8—C34	171.9 (2)
C20—C21—C26—C25	177.6 (2)

Hydrogen-bond geometry (Å, º) top

Cg7 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···N2	0.82	2.10	2.638 (2)	122
C15—H15···O6ⁱ	0.93	2.56	3.231 (3)	129
C16—H16···O2	0.93	2.59	3.405 (3)	146
C32—H32B···O3	0.97	2.55	3.413 (3)	148
C12—H12···Cg7ⁱⁱ	0.93	2.95	3.775 (3)	149

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

Experimental details

Crystal data
Chemical formula	C₃₄H₃₂N₂O₈
M_r	596.62
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.4251 (13), 7.8362 (8), 32.041 (4)
β (°)	91.313 (8)
V (Å³)	2867.9 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.22 × 0.2

Data collection
Diffractometer	Bruker SMART APEXII area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.976, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	27667, 7104, 3251
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.141, 0.99
No. of reflections	7104
No. of parameters	400
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.20

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg7 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···N2	0.82	2.10	2.638 (2)	122
C15—H15···O6ⁱ	0.93	2.56	3.231 (3)	129
C12—H12···Cg7ⁱⁱ	0.93	2.95	3.775 (3)	149

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

Acknowledgements

SS and DV thank the TBI X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the University Grants Commission (UGC & SAP) for financial support.

References

Arun, M., Joshi, S. N., Puranik, V. G., Bhawal, B. M. & Deshmukh, A. R. A. S. (2003). Tetrahedron, 59, 2309–2316. Web of Science CSD CrossRef CAS Google Scholar
Banik, B. K. & Becker, F. F. (2000). Tetrahedron Lett. 41, 6551–6554. Web of Science CrossRef CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Brakhage, A. A. (1998). Microbiol. Mol. Biol. Rev. 62, 547–585. Web of Science CAS PubMed Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. 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

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 68| Part 7| July 2012| Pages o2200-o2201

https://doi.org/10.1107/S1600536812027341

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

Methyl 11-hy­dr­oxy-9-[1-(4-meth­­oxy­phen­yl)-4-oxo-3-phen­­oxy­azetidin-2-yl]-18-oxo-10-oxa-2-aza­penta­cyclo­[9.7.0.01,8.02,6.012,17]octa­deca-12(17),13,15-triene-8-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 11-hydroxy-9-[1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin-2-yl]-18-oxo-10-oxa-2-azapentacyclo[9.7.0.0^1,8.0^2,6.0^12,17]octadeca-12(17),13,15-triene-8-carboxylate