organic compounds
Methyl 8-bromo-3-[1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-1-methyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b]pyrrole-3a-carboxylate
aDepartment of Physics, Presidency College, Chennai 600 005, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: aravindhanpresidency@gmail.com
In the title compound, C30H29BrN2O5, the β-lactam ring is essentially planar, with the O atom displaced from this plane by 0.856 (9) Å, and forming dihedral angles of 24.35 (13) and 89.42 (14)° with the planes of the benzene substituent groups on this ring. The tetrahydropyran ring adopts an with the C atom bearing the β-lactam ring as the flap. In the crystal, weak C—H⋯O hydrogen bonds with carboxyl and tetrahydropyran O-atom acceptors give rise to a chain structure extending along the b-axis direction.
Related literature
For general background to β-lactams, see: Brakhage (1998). For a related structure, see: Sundaramoorthy et al. (2012). For conformation of the molecular structure, see: Nardelli (1983).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2008); cell APEX2 and SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
10.1107/S1600536813024963/zs2268sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813024963/zs2268Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813024963/zs2268Isup3.cml
A solution of (Z)-methyl 2-[(4-bromo-2-formylphenoxy)methyl]-3-[1-(4-methoxyphenyl)- 4-oxo-3-phenylazetidin-2-yl]acrylate (1 mmol) and sarcosine (1.2 mmol) was refluxed in dry acetonitrile. Completion of the reaction was confirmed by TLC analysis. The solvent was then removed under vacuum, then diluted with dichloromethane and washed with brine and water. The organic layer was separated and removed and the residue was subjected to
using ethyl acetate and hexane (2:8) as an affording the cycloadduct. The product was dissolved in ethyl acetate and the resulting solution was allowed to slowly evaporate over 48 h, resulting in the formation of crystals suitable for the single-crystal X-ray diffraction analysis.Hydrogen atoms were included at calculated positions with C—H ranging from 0.93 to 0.97 Å and treated using a riding model with displacement parameters Uiso(H) = 1.2Ueq(C)(methine, methylene and aromatic), or 1.5Ueq(C)(methyl). The
for the molecule was not determined definitively but the local configuration for the five chiral centres [C1(R),C2(R), C16(S),C18(R),C19(R) for the trivial atom numbering scheme used] was assigned on the basis of the [0.006 (5) for 2910 Friedel pairs].Data collection: APEX2 (Bruker, 2008); cell
APEX2 and SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).C30H29BrN2O5 | F(000) = 596 |
Mr = 577.46 | Dx = 1.433 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 8834 reflections |
a = 10.904 (5) Å | θ = 2.1–31.2° |
b = 10.765 (5) Å | µ = 1.58 mm−1 |
c = 11.405 (5) Å | T = 293 K |
β = 91.681 (5)° | Block, colourless |
V = 1338.2 (11) Å3 | 0.25 × 0.20 × 0.20 mm |
Z = 2 |
Bruker Kappa APEXII CCD diffractometer | 6511 independent reflections |
Radiation source: fine-focus sealed tube | 5355 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ω and ϕ scans | θmax = 28.6°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker 2008) | h = −14→14 |
Tmin = 0.979, Tmax = 0.983 | k = −12→14 |
28413 measured reflections | l = −15→15 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.065 | w = 1/[σ2(Fo2) + (0.0292P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max = 0.001 |
6511 reflections | Δρmax = 0.42 e Å−3 |
343 parameters | Δρmin = −0.21 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 2910 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.006 (5) |
C30H29BrN2O5 | V = 1338.2 (11) Å3 |
Mr = 577.46 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 10.904 (5) Å | µ = 1.58 mm−1 |
b = 10.765 (5) Å | T = 293 K |
c = 11.405 (5) Å | 0.25 × 0.20 × 0.20 mm |
β = 91.681 (5)° |
Bruker Kappa APEXII CCD diffractometer | 6511 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker 2008) | 5355 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.983 | Rint = 0.037 |
28413 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.065 | Δρmax = 0.42 e Å−3 |
S = 0.96 | Δρmin = −0.21 e Å−3 |
6511 reflections | Absolute structure: Flack (1983), 2910 Friedel pairs |
343 parameters | Absolute structure parameter: 0.006 (5) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
Br | 0.400982 (17) | 0.56044 (2) | 0.676638 (19) | 0.05395 (8) | |
O1 | 0.31783 (11) | 0.04829 (18) | 1.46057 (11) | 0.0508 (4) | |
O3 | −0.04275 (11) | 0.10982 (13) | 1.05918 (12) | 0.0453 (4) | |
C18 | 0.26814 (15) | 0.19721 (18) | 0.96769 (15) | 0.0300 (4) | |
H18 | 0.2783 | 0.2600 | 1.0295 | 0.036* | |
N2 | 0.24186 (14) | −0.05496 (15) | 1.29243 (13) | 0.0346 (4) | |
C19 | 0.15975 (16) | 0.11200 (16) | 0.99504 (15) | 0.0288 (4) | |
C17 | 0.35296 (16) | 0.0409 (2) | 1.08186 (17) | 0.0460 (5) | |
H17A | 0.3798 | 0.0894 | 1.1495 | 0.055* | |
H17B | 0.3987 | −0.0364 | 1.0816 | 0.055* | |
C11 | −0.00677 (18) | 0.12700 (19) | 1.39886 (16) | 0.0389 (4) | |
H11 | 0.0019 | 0.0414 | 1.4062 | 0.047* | |
O5 | 0.08439 (12) | 0.12441 (13) | 0.79140 (12) | 0.0415 (3) | |
C1 | 0.16563 (17) | 0.01715 (17) | 1.20853 (15) | 0.0322 (4) | |
H1 | 0.0796 | −0.0092 | 1.2090 | 0.039* | |
C10 | 0.08118 (17) | 0.19488 (18) | 1.34185 (15) | 0.0334 (4) | |
C20 | 0.12485 (17) | 0.04159 (18) | 0.88268 (15) | 0.0352 (4) | |
H20A | 0.1953 | −0.0050 | 0.8569 | 0.042* | |
H20B | 0.0599 | −0.0171 | 0.8986 | 0.042* | |
N1 | 0.37101 (13) | 0.11007 (16) | 0.97373 (13) | 0.0408 (4) | |
C23 | 0.32095 (15) | 0.36424 (19) | 0.82176 (15) | 0.0342 (4) | |
H23 | 0.3774 | 0.3968 | 0.8762 | 0.041* | |
C2 | 0.18887 (17) | 0.13190 (18) | 1.28871 (17) | 0.0349 (4) | |
H2 | 0.2427 | 0.1922 | 1.2515 | 0.042* | |
O4 | 0.04486 (13) | 0.29512 (13) | 1.04029 (15) | 0.0551 (4) | |
C7 | 0.34735 (18) | −0.4280 (2) | 1.28407 (17) | 0.0469 (5) | |
C21 | 0.16422 (17) | 0.21901 (17) | 0.76857 (16) | 0.0332 (4) | |
C27 | 0.04967 (16) | 0.18462 (18) | 1.03411 (15) | 0.0321 (4) | |
C8 | 0.2427 (2) | −0.3891 (2) | 1.2253 (2) | 0.0476 (5) | |
H8 | 0.1955 | −0.4460 | 1.1823 | 0.057* | |
C22 | 0.25184 (15) | 0.25992 (17) | 0.85049 (15) | 0.0299 (4) | |
C4 | 0.27709 (16) | −0.18125 (18) | 1.29142 (15) | 0.0340 (4) | |
C13 | −0.1218 (2) | 0.3116 (3) | 1.43409 (19) | 0.0557 (6) | |
H13 | −0.1902 | 0.3504 | 1.4642 | 0.067* | |
C3 | 0.26291 (15) | 0.0416 (2) | 1.36740 (15) | 0.0367 (4) | |
C9 | 0.20708 (18) | −0.2667 (2) | 1.22956 (18) | 0.0415 (5) | |
H9 | 0.1353 | −0.2416 | 1.1904 | 0.050* | |
C14 | −0.0354 (2) | 0.3795 (2) | 1.37900 (18) | 0.0562 (6) | |
H14 | −0.0446 | 0.4651 | 1.3718 | 0.067* | |
O2 | 0.37564 (17) | −0.55173 (16) | 1.27246 (18) | 0.0755 (5) | |
C16 | 0.21506 (16) | 0.01548 (18) | 1.08484 (16) | 0.0348 (4) | |
H16 | 0.2005 | −0.0677 | 1.0523 | 0.042* | |
C25 | 0.22241 (19) | 0.3750 (2) | 0.63222 (17) | 0.0424 (5) | |
H25 | 0.2147 | 0.4121 | 0.5587 | 0.051* | |
C15 | 0.0665 (2) | 0.3214 (2) | 1.33349 (17) | 0.0453 (5) | |
H15 | 0.1256 | 0.3688 | 1.2969 | 0.054* | |
C26 | 0.1497 (2) | 0.2749 (2) | 0.66016 (17) | 0.0456 (5) | |
H26 | 0.0911 | 0.2453 | 0.6062 | 0.055* | |
C12 | −0.10739 (19) | 0.1852 (2) | 1.44493 (18) | 0.0488 (5) | |
H12 | −0.1657 | 0.1387 | 1.4835 | 0.059* | |
C6 | 0.4169 (2) | −0.3436 (2) | 1.34782 (19) | 0.0480 (5) | |
H6 | 0.4871 | −0.3699 | 1.3889 | 0.058* | |
C5 | 0.38299 (18) | −0.2206 (2) | 1.35108 (18) | 0.0414 (5) | |
H5 | 0.4310 | −0.1637 | 1.3932 | 0.050* | |
C24 | 0.30595 (17) | 0.41881 (18) | 0.71383 (17) | 0.0363 (4) | |
C30 | 0.4857 (4) | −0.5944 (3) | 1.3249 (4) | 0.1324 (18) | |
H30A | 0.4940 | −0.6819 | 1.3109 | 0.199* | |
H30B | 0.4850 | −0.5793 | 1.4078 | 0.199* | |
H30C | 0.5535 | −0.5512 | 1.2918 | 0.199* | |
C28 | −0.15281 (18) | 0.1671 (2) | 1.1007 (2) | 0.0540 (6) | |
H28A | −0.2127 | 0.1041 | 1.1157 | 0.081* | |
H28B | −0.1850 | 0.2235 | 1.0423 | 0.081* | |
H28C | −0.1340 | 0.2119 | 1.1718 | 0.081* | |
C29 | 0.49131 (19) | 0.1676 (3) | 0.9721 (2) | 0.0615 (7) | |
H29A | 0.4995 | 0.2127 | 0.9002 | 0.092* | |
H29B | 0.5534 | 0.1045 | 0.9780 | 0.092* | |
H29C | 0.5006 | 0.2237 | 1.0372 | 0.092* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br | 0.04262 (11) | 0.05682 (14) | 0.06218 (14) | −0.01288 (11) | −0.00226 (8) | 0.02366 (12) |
O1 | 0.0458 (7) | 0.0643 (11) | 0.0415 (7) | 0.0033 (9) | −0.0118 (6) | −0.0051 (8) |
O3 | 0.0307 (7) | 0.0432 (8) | 0.0623 (9) | −0.0010 (6) | 0.0053 (6) | 0.0079 (7) |
C18 | 0.0282 (9) | 0.0361 (10) | 0.0254 (9) | 0.0008 (7) | −0.0022 (7) | 0.0006 (7) |
N2 | 0.0394 (9) | 0.0372 (9) | 0.0269 (8) | 0.0017 (7) | −0.0042 (7) | 0.0046 (7) |
C19 | 0.0321 (9) | 0.0270 (8) | 0.0273 (9) | 0.0027 (7) | 0.0005 (7) | 0.0026 (7) |
C17 | 0.0363 (9) | 0.0596 (16) | 0.0423 (10) | 0.0153 (10) | 0.0049 (8) | 0.0145 (11) |
C11 | 0.0426 (11) | 0.0362 (10) | 0.0378 (11) | −0.0026 (9) | 0.0016 (9) | −0.0025 (8) |
O5 | 0.0512 (8) | 0.0370 (8) | 0.0354 (7) | −0.0124 (6) | −0.0145 (6) | 0.0052 (6) |
C1 | 0.0332 (9) | 0.0333 (10) | 0.0299 (9) | 0.0024 (7) | −0.0002 (7) | 0.0061 (7) |
C10 | 0.0394 (10) | 0.0340 (10) | 0.0264 (9) | −0.0004 (8) | −0.0040 (8) | −0.0015 (7) |
C20 | 0.0440 (10) | 0.0283 (11) | 0.0330 (9) | −0.0001 (8) | −0.0034 (7) | 0.0024 (8) |
N1 | 0.0316 (8) | 0.0588 (11) | 0.0324 (8) | 0.0110 (7) | 0.0052 (7) | 0.0111 (7) |
C23 | 0.0284 (9) | 0.0430 (11) | 0.0309 (9) | −0.0042 (8) | −0.0035 (7) | 0.0012 (8) |
C2 | 0.0336 (10) | 0.0371 (11) | 0.0340 (10) | −0.0033 (8) | 0.0022 (8) | 0.0023 (8) |
O4 | 0.0498 (9) | 0.0317 (9) | 0.0850 (12) | 0.0077 (6) | 0.0228 (8) | 0.0021 (8) |
C7 | 0.0531 (11) | 0.0383 (11) | 0.0492 (11) | 0.0043 (12) | 0.0001 (9) | 0.0079 (11) |
C21 | 0.0370 (10) | 0.0316 (10) | 0.0309 (10) | −0.0014 (8) | −0.0029 (8) | 0.0007 (8) |
C27 | 0.0327 (10) | 0.0354 (11) | 0.0282 (9) | 0.0014 (8) | 0.0008 (7) | 0.0053 (8) |
C8 | 0.0491 (12) | 0.0418 (12) | 0.0516 (13) | −0.0047 (9) | −0.0031 (10) | 0.0038 (10) |
C22 | 0.0288 (9) | 0.0337 (10) | 0.0272 (9) | 0.0016 (7) | −0.0005 (7) | −0.0010 (7) |
C4 | 0.0354 (10) | 0.0376 (11) | 0.0291 (9) | 0.0013 (8) | 0.0027 (8) | 0.0094 (8) |
C13 | 0.0561 (14) | 0.0730 (18) | 0.0377 (12) | 0.0260 (12) | −0.0030 (10) | −0.0154 (12) |
C3 | 0.0309 (8) | 0.0443 (13) | 0.0350 (9) | −0.0008 (9) | 0.0035 (7) | 0.0034 (9) |
C9 | 0.0370 (10) | 0.0392 (11) | 0.0478 (12) | −0.0001 (9) | −0.0059 (9) | 0.0113 (9) |
C14 | 0.0914 (18) | 0.0418 (13) | 0.0351 (11) | 0.0229 (12) | −0.0043 (12) | −0.0045 (10) |
O2 | 0.0852 (13) | 0.0409 (10) | 0.0990 (15) | 0.0164 (9) | −0.0241 (11) | −0.0022 (10) |
C16 | 0.0384 (10) | 0.0344 (10) | 0.0318 (9) | 0.0091 (7) | 0.0022 (8) | 0.0023 (7) |
C25 | 0.0528 (12) | 0.0413 (11) | 0.0325 (10) | 0.0003 (9) | −0.0065 (9) | 0.0095 (9) |
C15 | 0.0664 (13) | 0.0359 (11) | 0.0336 (10) | 0.0012 (10) | 0.0012 (10) | 0.0011 (8) |
C26 | 0.0568 (13) | 0.0434 (12) | 0.0357 (11) | −0.0075 (10) | −0.0177 (9) | 0.0023 (9) |
C12 | 0.0403 (11) | 0.0644 (16) | 0.0419 (12) | −0.0023 (10) | 0.0018 (9) | −0.0107 (11) |
C6 | 0.0474 (12) | 0.0491 (13) | 0.0470 (12) | 0.0131 (10) | −0.0074 (10) | 0.0063 (10) |
C5 | 0.0407 (11) | 0.0453 (12) | 0.0379 (11) | −0.0002 (9) | −0.0040 (8) | 0.0042 (9) |
C24 | 0.0318 (10) | 0.0358 (11) | 0.0415 (11) | −0.0011 (8) | 0.0032 (8) | 0.0070 (8) |
C30 | 0.150 (4) | 0.070 (2) | 0.173 (4) | 0.060 (2) | −0.077 (3) | −0.026 (3) |
C28 | 0.0317 (11) | 0.0705 (16) | 0.0601 (14) | 0.0056 (10) | 0.0089 (10) | 0.0124 (12) |
C29 | 0.0323 (11) | 0.098 (2) | 0.0544 (14) | 0.0065 (12) | 0.0057 (10) | 0.0240 (14) |
Br—C24 | 1.898 (2) | O4—C27 | 1.193 (2) |
O1—C3 | 1.206 (2) | C7—O2 | 1.375 (3) |
O3—C27 | 1.328 (2) | C7—C8 | 1.371 (3) |
O3—C28 | 1.442 (2) | C7—C6 | 1.377 (3) |
C18—N1 | 1.462 (2) | C21—C26 | 1.380 (3) |
C18—C22 | 1.503 (2) | C21—C22 | 1.388 (3) |
C18—C19 | 1.535 (3) | C8—C9 | 1.375 (3) |
C18—H18 | 0.9800 | C8—H8 | 0.9300 |
N2—C3 | 1.361 (3) | C4—C9 | 1.377 (3) |
N2—C4 | 1.413 (3) | C4—C5 | 1.389 (3) |
N2—C1 | 1.471 (2) | C13—C14 | 1.361 (4) |
C19—C27 | 1.511 (3) | C13—C12 | 1.374 (4) |
C19—C20 | 1.527 (3) | C13—H13 | 0.9300 |
C19—C16 | 1.567 (3) | C9—H9 | 0.9300 |
C17—N1 | 1.459 (2) | C14—C15 | 1.389 (3) |
C17—C16 | 1.530 (3) | C14—H14 | 0.9300 |
C17—H17A | 0.9700 | O2—C30 | 1.403 (4) |
C17—H17B | 0.9700 | C16—H16 | 0.9800 |
C11—C12 | 1.381 (3) | C25—C24 | 1.367 (3) |
C11—C10 | 1.383 (3) | C25—C26 | 1.381 (3) |
C11—H11 | 0.9300 | C25—H25 | 0.9300 |
O5—C21 | 1.370 (2) | C15—H15 | 0.9300 |
O5—C20 | 1.431 (2) | C26—H26 | 0.9300 |
C1—C16 | 1.525 (3) | C12—H12 | 0.9300 |
C1—C2 | 1.553 (3) | C6—C5 | 1.376 (3) |
C1—H1 | 0.9800 | C6—H6 | 0.9300 |
C10—C15 | 1.375 (3) | C5—H5 | 0.9300 |
C10—C2 | 1.499 (3) | C30—H30A | 0.9600 |
C20—H20A | 0.9700 | C30—H30B | 0.9600 |
C20—H20B | 0.9700 | C30—H30C | 0.9600 |
N1—C29 | 1.451 (3) | C28—H28A | 0.9600 |
C23—C24 | 1.369 (3) | C28—H28B | 0.9600 |
C23—C22 | 1.397 (3) | C28—H28C | 0.9600 |
C23—H23 | 0.9300 | C29—H29A | 0.9600 |
C2—C3 | 1.536 (3) | C29—H29B | 0.9600 |
C2—H2 | 0.9800 | C29—H29C | 0.9600 |
C27—O3—C28 | 117.11 (17) | C21—C22—C23 | 117.56 (16) |
N1—C18—C22 | 113.60 (14) | C21—C22—C18 | 121.13 (16) |
N1—C18—C19 | 101.61 (15) | C23—C22—C18 | 121.27 (15) |
C22—C18—C19 | 112.16 (14) | C9—C4—C5 | 119.19 (19) |
N1—C18—H18 | 109.7 | C9—C4—N2 | 120.04 (17) |
C22—C18—H18 | 109.7 | C5—C4—N2 | 120.76 (18) |
C19—C18—H18 | 109.7 | C14—C13—C12 | 119.6 (2) |
C3—N2—C4 | 134.35 (16) | C14—C13—H13 | 120.2 |
C3—N2—C1 | 95.01 (15) | C12—C13—H13 | 120.2 |
C4—N2—C1 | 130.64 (16) | O1—C3—N2 | 132.0 (2) |
C27—C19—C20 | 108.89 (15) | O1—C3—C2 | 135.7 (2) |
C27—C19—C18 | 111.95 (15) | N2—C3—C2 | 92.30 (15) |
C20—C19—C18 | 107.48 (14) | C8—C9—C4 | 120.37 (19) |
C27—C19—C16 | 116.38 (14) | C8—C9—H9 | 119.8 |
C20—C19—C16 | 107.51 (15) | C4—C9—H9 | 119.8 |
C18—C19—C16 | 104.19 (14) | C13—C14—C15 | 120.2 (2) |
N1—C17—C16 | 105.50 (15) | C13—C14—H14 | 119.9 |
N1—C17—H17A | 110.6 | C15—C14—H14 | 119.9 |
C16—C17—H17A | 110.6 | C7—O2—C30 | 117.9 (2) |
N1—C17—H17B | 110.6 | C1—C16—C17 | 113.12 (16) |
C16—C17—H17B | 110.6 | C1—C16—C19 | 117.20 (15) |
H17A—C17—H17B | 108.8 | C17—C16—C19 | 103.09 (15) |
C12—C11—C10 | 120.6 (2) | C1—C16—H16 | 107.7 |
C12—C11—H11 | 119.7 | C17—C16—H16 | 107.7 |
C10—C11—H11 | 119.7 | C19—C16—H16 | 107.7 |
C21—O5—C20 | 114.68 (14) | C24—C25—C26 | 119.22 (18) |
N2—C1—C16 | 112.79 (15) | C24—C25—H25 | 120.4 |
N2—C1—C2 | 87.56 (14) | C26—C25—H25 | 120.4 |
C16—C1—C2 | 119.87 (15) | C10—C15—C14 | 120.8 (2) |
N2—C1—H1 | 111.5 | C10—C15—H15 | 119.6 |
C16—C1—H1 | 111.5 | C14—C15—H15 | 119.6 |
C2—C1—H1 | 111.5 | C25—C26—C21 | 119.68 (19) |
C15—C10—C11 | 118.39 (19) | C25—C26—H26 | 120.2 |
C15—C10—C2 | 120.73 (18) | C21—C26—H26 | 120.2 |
C11—C10—C2 | 120.88 (18) | C13—C12—C11 | 120.3 (2) |
O5—C20—C19 | 111.42 (16) | C13—C12—H12 | 119.8 |
O5—C20—H20A | 109.3 | C11—C12—H12 | 119.8 |
C19—C20—H20A | 109.3 | C5—C6—C7 | 120.3 (2) |
O5—C20—H20B | 109.3 | C5—C6—H6 | 119.8 |
C19—C20—H20B | 109.3 | C7—C6—H6 | 119.8 |
H20A—C20—H20B | 108.0 | C6—C5—C4 | 120.02 (19) |
C29—N1—C17 | 111.89 (16) | C6—C5—H5 | 120.0 |
C29—N1—C18 | 114.70 (18) | C4—C5—H5 | 120.0 |
C17—N1—C18 | 104.17 (13) | C25—C24—C23 | 121.57 (18) |
C24—C23—C22 | 120.31 (16) | C25—C24—Br | 118.84 (15) |
C24—C23—H23 | 119.8 | C23—C24—Br | 119.59 (14) |
C22—C23—H23 | 119.8 | O2—C30—H30A | 109.5 |
C10—C2—C3 | 117.03 (15) | O2—C30—H30B | 109.5 |
C10—C2—C1 | 118.78 (16) | H30A—C30—H30B | 109.5 |
C3—C2—C1 | 85.10 (15) | O2—C30—H30C | 109.5 |
C10—C2—H2 | 111.2 | H30A—C30—H30C | 109.5 |
C3—C2—H2 | 111.2 | H30B—C30—H30C | 109.5 |
C1—C2—H2 | 111.2 | O3—C28—H28A | 109.5 |
O2—C7—C8 | 115.7 (2) | O3—C28—H28B | 109.5 |
O2—C7—C6 | 124.6 (2) | H28A—C28—H28B | 109.5 |
C8—C7—C6 | 119.6 (2) | O3—C28—H28C | 109.5 |
O5—C21—C26 | 115.94 (16) | H28A—C28—H28C | 109.5 |
O5—C21—C22 | 122.46 (16) | H28B—C28—H28C | 109.5 |
C26—C21—C22 | 121.56 (17) | N1—C29—H29A | 109.5 |
O4—C27—O3 | 123.86 (17) | N1—C29—H29B | 109.5 |
O4—C27—C19 | 124.76 (17) | H29A—C29—H29B | 109.5 |
O3—C27—C19 | 111.37 (17) | N1—C29—H29C | 109.5 |
C7—C8—C9 | 120.4 (2) | H29A—C29—H29C | 109.5 |
C7—C8—H8 | 119.8 | H29B—C29—H29C | 109.5 |
C9—C8—H8 | 119.8 | ||
N1—C18—C19—C27 | 160.79 (14) | N1—C18—C22—C23 | −82.7 (2) |
C22—C18—C19—C27 | −77.54 (19) | C19—C18—C22—C23 | 162.77 (16) |
N1—C18—C19—C20 | −79.68 (16) | C3—N2—C4—C9 | 155.5 (2) |
C22—C18—C19—C20 | 41.99 (19) | C1—N2—C4—C9 | −23.8 (3) |
N1—C18—C19—C16 | 34.21 (16) | C3—N2—C4—C5 | −25.4 (3) |
C22—C18—C19—C16 | 155.88 (14) | C1—N2—C4—C5 | 155.29 (18) |
C3—N2—C1—C16 | 122.88 (16) | C4—N2—C3—O1 | −2.0 (3) |
C4—N2—C1—C16 | −57.6 (2) | C1—N2—C3—O1 | 177.5 (2) |
C3—N2—C1—C2 | 1.36 (14) | C4—N2—C3—C2 | 179.15 (19) |
C4—N2—C1—C2 | −179.14 (18) | C1—N2—C3—C2 | −1.38 (14) |
C12—C11—C10—C15 | 0.7 (3) | C10—C2—C3—O1 | −57.5 (3) |
C12—C11—C10—C2 | −178.30 (19) | C1—C2—C3—O1 | −177.5 (2) |
C21—O5—C20—C19 | 53.2 (2) | C10—C2—C3—N2 | 121.22 (17) |
C27—C19—C20—O5 | 58.75 (18) | C1—C2—C3—N2 | 1.30 (13) |
C18—C19—C20—O5 | −62.71 (18) | C7—C8—C9—C4 | 1.0 (3) |
C16—C19—C20—O5 | −174.35 (13) | C5—C4—C9—C8 | −1.1 (3) |
C16—C17—N1—C29 | 165.70 (18) | N2—C4—C9—C8 | 178.07 (18) |
C16—C17—N1—C18 | 41.2 (2) | C12—C13—C14—C15 | 0.3 (3) |
C22—C18—N1—C29 | 69.9 (2) | C8—C7—O2—C30 | 176.1 (3) |
C19—C18—N1—C29 | −169.48 (16) | C6—C7—O2—C30 | −2.9 (4) |
C22—C18—N1—C17 | −167.51 (16) | N2—C1—C16—C17 | −46.8 (2) |
C19—C18—N1—C17 | −46.84 (18) | C2—C1—C16—C17 | 54.0 (2) |
C15—C10—C2—C3 | 130.1 (2) | N2—C1—C16—C19 | −166.55 (15) |
C11—C10—C2—C3 | −50.9 (3) | C2—C1—C16—C19 | −65.7 (2) |
C15—C10—C2—C1 | −130.03 (19) | N1—C17—C16—C1 | −145.59 (17) |
C11—C10—C2—C1 | 49.0 (2) | N1—C17—C16—C19 | −18.0 (2) |
N2—C1—C2—C10 | −119.46 (17) | C27—C19—C16—C1 | −8.8 (2) |
C16—C1—C2—C10 | 125.54 (18) | C20—C19—C16—C1 | −131.17 (17) |
N2—C1—C2—C3 | −1.21 (12) | C18—C19—C16—C1 | 114.96 (17) |
C16—C1—C2—C3 | −116.21 (17) | C27—C19—C16—C17 | −133.75 (17) |
C20—O5—C21—C26 | 159.63 (18) | C20—C19—C16—C17 | 103.88 (17) |
C20—O5—C21—C22 | −22.6 (2) | C18—C19—C16—C17 | −9.99 (18) |
C28—O3—C27—O4 | −2.6 (3) | C11—C10—C15—C14 | −1.3 (3) |
C28—O3—C27—C19 | 178.39 (16) | C2—C10—C15—C14 | 177.70 (18) |
C20—C19—C27—O4 | −116.7 (2) | C13—C14—C15—C10 | 0.8 (3) |
C18—C19—C27—O4 | 2.0 (3) | C24—C25—C26—C21 | −1.5 (3) |
C16—C19—C27—O4 | 121.6 (2) | O5—C21—C26—C25 | 176.88 (19) |
C20—C19—C27—O3 | 62.25 (19) | C22—C21—C26—C25 | −0.9 (3) |
C18—C19—C27—O3 | −179.05 (15) | C14—C13—C12—C11 | −0.9 (3) |
C16—C19—C27—O3 | −59.4 (2) | C10—C11—C12—C13 | 0.4 (3) |
O2—C7—C8—C9 | −178.98 (19) | O2—C7—C6—C5 | 177.9 (2) |
C6—C7—C8—C9 | 0.1 (3) | C8—C7—C6—C5 | −1.1 (3) |
O5—C21—C22—C23 | −174.34 (16) | C7—C6—C5—C4 | 1.0 (3) |
C26—C21—C22—C23 | 3.3 (3) | C9—C4—C5—C6 | 0.1 (3) |
O5—C21—C22—C18 | 3.3 (3) | N2—C4—C5—C6 | −179.07 (18) |
C26—C21—C22—C18 | −179.12 (19) | C26—C25—C24—C23 | 1.4 (3) |
C24—C23—C22—C21 | −3.4 (3) | C26—C25—C24—Br | −177.57 (16) |
C24—C23—C22—C18 | 179.01 (17) | C22—C23—C24—C25 | 1.1 (3) |
N1—C18—C22—C21 | 99.8 (2) | C22—C23—C24—Br | −179.94 (14) |
C19—C18—C22—C21 | −14.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C20—H20B···O4i | 0.97 | 2.43 | 3.366 (3) | 161 |
C14—H14···O5ii | 0.93 | 2.56 | 3.309 (3) | 138 |
Symmetry codes: (i) −x, y−1/2, −z+2; (ii) −x, y+1/2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C20—H20B···O4i | 0.97 | 2.43 | 3.366 (3) | 161 |
C14—H14···O5ii | 0.93 | 2.56 | 3.309 (3) | 138 |
Symmetry codes: (i) −x, y−1/2, −z+2; (ii) −x, y+1/2, −z+2. |
Acknowledgements
SA thanks the UGC-India for financial support.
References
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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, C30H29BrN2O5, was carried out and is reported herein. In this compound (Fig. 1), the four-membered ring of the β-lactam fragment (N2/C1–C3) is essentially planar (r.m.s. deviation = 0.0122 Å), with O1 displaced from the plane by 0.856 (9) Å. The mean-planes of the benzene rings of the two benzene substituent groups defined by C4–C9 and C10–C15 are inclined at dihedral angles 24.35 (13)° and 89.42 (14) °, respectively, with respect to four-membered β-lactam ring. The pyrrolidine ring (N1/C16/C17/C18/C19) adopts an envelope conformation, defined by the asymmetry parameters (Nardelli, 1983), DS (N2) = 0.0789 (19) Å and D2 (C16) = 0.0228 (15) Å whereas the pyran ring [(O5/C18/C19/C20/C21/C22) adopts a C19-envelope/sofa conformation with C19 displaced by 0.385 (1) Å from the least-squares planes formed by the remaining ring atoms.
In the crystal, the structure is stabilized by weak intermolecular aromatic C14—H···O5tetrahydropyran and tetrahydropyran C20—H···O4carboxyl hydrogen-bonding interactions (Table 1), giving a one-dimensional chain extending along b (Fig. 2). Present also in the structure are two intramolecular C—H···β-lactam interactions involving aromatic C11—H11···Cg [2.932 (4) Å; C—H···Cg, angle 94°] and piperidine C17—H17A···Cg [2.842 (4) Å; C—H···Cg angle, 100°].