



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809015104/bt2932sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536809015104/bt2932Isup2.hkl |
CCDC reference: 699268
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.042
- wR factor = 0.138
- Data-to-parameter ratio = 24.2
checkCIF/PLATON results
No syntax errors found
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 31.65 From the CIF: _reflns_number_total 9003 Count of symmetry unique reflns 5132 Completeness (_total/calc) 175.43% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3871 Fraction of Friedel pairs measured 0.754 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_4_G The Model has Chirality at C9 (Verify) .... S PLAT791_ALERT_4_G The Model has Chirality at C10 (Verify) .... R PLAT791_ALERT_4_G The Model has Chirality at C11 (Verify) .... R PLAT791_ALERT_4_G The Model has Chirality at C12 (Verify) .... R PLAT791_ALERT_4_G The Model has Chirality at C13 (Verify) .... S PLAT791_ALERT_4_G The Model has Chirality at C14 (Verify) .... R PLAT791_ALERT_4_G The Model has Chirality at C15 (Verify) .... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 10 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 8 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A mixture of D-glucose derived nitrone (0.5 mmol) and maleimide (0.5 mmol) was refluxed in dry toluene (10 ml) until completion of the reaction as evidenced by TLC analysis. The solvent was evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel (Merck, 100–200 mesh, ethylacetate-petroleum ether (1:9). Single crystals of the title compound suitable for X-ray diffraction were obtained by recrystallization from ethanol.
All H atoms were positioned geometrically, with C—H = 0.93–0.98 Å and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.
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: 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).
C31H29BrN2O7 | F(000) = 640 |
Mr = 621.47 | Dx = 1.459 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 5502 reflections |
a = 15.0680 (12) Å | θ = 2.5–25° |
b = 6.6801 (5) Å | µ = 1.51 mm−1 |
c = 15.8550 (12) Å | T = 293 K |
β = 117.578 (2)° | Needle, colourless |
V = 1414.57 (19) Å3 | 0.3 × 0.2 × 0.2 mm |
Z = 2 |
Bruker Kappa APEXII CCD diffractometer | 9003 independent reflections |
Radiation source: fine-focus sealed tube | 5502 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω and ϕ scans | θmax = 31.7°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker 2004) | h = −22→22 |
Tmin = 0.734, Tmax = 0.740 | k = −9→8 |
20450 measured reflections | l = −23→23 |
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)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.138 | w = 1/[σ2(Fo2) + (0.066P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
9003 reflections | Δρmax = 0.66 e Å−3 |
372 parameters | Δρmin = −0.38 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 3886 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.001 (8) |
C31H29BrN2O7 | V = 1414.57 (19) Å3 |
Mr = 621.47 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 15.0680 (12) Å | µ = 1.51 mm−1 |
b = 6.6801 (5) Å | T = 293 K |
c = 15.8550 (12) Å | 0.3 × 0.2 × 0.2 mm |
β = 117.578 (2)° |
Bruker Kappa APEXII CCD diffractometer | 9003 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker 2004) | 5502 reflections with I > 2σ(I) |
Tmin = 0.734, Tmax = 0.740 | Rint = 0.027 |
20450 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.138 | Δρmax = 0.66 e Å−3 |
S = 1.00 | Δρmin = −0.38 e Å−3 |
9003 reflections | Absolute structure: Flack (1983), 3886 Friedel pairs |
372 parameters | Absolute structure parameter: −0.001 (8) |
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 | ||
C1 | 0.64016 (18) | 0.3845 (4) | 0.35916 (18) | 0.0430 (6) | |
H1 | 0.6865 | 0.4725 | 0.4028 | 0.052* | |
C2 | 0.5464 (2) | 0.4517 (5) | 0.2949 (2) | 0.0524 (7) | |
H2 | 0.5293 | 0.5853 | 0.2952 | 0.063* | |
C3 | 0.4785 (2) | 0.3213 (5) | 0.2304 (2) | 0.0557 (7) | |
C4 | 0.5020 (2) | 0.1225 (5) | 0.2294 (2) | 0.0576 (8) | |
H4 | 0.4553 | 0.0349 | 0.1858 | 0.069* | |
C5 | 0.5958 (2) | 0.0545 (4) | 0.2940 (2) | 0.0462 (6) | |
H5 | 0.6125 | −0.0796 | 0.2942 | 0.055* | |
C6 | 0.66469 (18) | 0.1858 (4) | 0.35820 (16) | 0.0359 (5) | |
C7 | 0.7771 (2) | −0.0588 (4) | 0.47898 (17) | 0.0415 (5) | |
C8 | 0.85005 (18) | 0.2249 (4) | 0.45433 (17) | 0.0381 (5) | |
C9 | 0.93114 (18) | 0.1327 (4) | 0.54302 (17) | 0.0370 (5) | |
H9 | 0.9931 | 0.1105 | 0.5385 | 0.044* | |
C10 | 0.88614 (19) | −0.0602 (4) | 0.55592 (17) | 0.0427 (5) | |
H10 | 0.9220 | −0.1772 | 0.5498 | 0.051* | |
C11 | 0.94837 (17) | 0.2561 (3) | 0.63122 (16) | 0.0340 (5) | |
H11 | 0.9266 | 0.3948 | 0.6132 | 0.041* | |
C12 | 1.05597 (18) | 0.2501 (4) | 0.70747 (16) | 0.0352 (5) | |
H12 | 1.0775 | 0.1109 | 0.7240 | 0.042* | |
C13 | 1.07749 (18) | 0.3678 (3) | 0.79726 (16) | 0.0347 (5) | |
H13 | 1.0594 | 0.2926 | 0.8402 | 0.042* | |
C14 | 1.18993 (18) | 0.3982 (4) | 0.83916 (16) | 0.0379 (5) | |
H14 | 1.2135 | 0.5202 | 0.8776 | 0.045* | |
C15 | 1.20853 (17) | 0.3989 (4) | 0.75221 (16) | 0.0402 (5) | |
H15 | 1.2319 | 0.5306 | 0.7437 | 0.048* | |
C16 | 1.3149 (2) | 0.1722 (4) | 0.86285 (19) | 0.0447 (6) | |
C17 | 1.3205 (3) | −0.0535 (6) | 0.8586 (3) | 0.0690 (9) | |
H17A | 1.3361 | −0.1092 | 0.9197 | 0.104* | |
H17B | 1.3718 | −0.0898 | 0.8415 | 0.104* | |
H17C | 1.2572 | −0.1047 | 0.8118 | 0.104* | |
C18 | 1.4135 (2) | 0.2643 (7) | 0.9303 (3) | 0.0759 (11) | |
H18A | 1.4063 | 0.4071 | 0.9304 | 0.114* | |
H18B | 1.4629 | 0.2314 | 0.9104 | 0.114* | |
H18C | 1.4342 | 0.2134 | 0.9933 | 0.114* | |
C19 | 0.9839 (2) | 0.6190 (4) | 0.82909 (19) | 0.0432 (6) | |
H19A | 0.9439 | 0.5111 | 0.8349 | 0.052* | |
H19B | 0.9392 | 0.7302 | 0.7980 | 0.052* | |
C20 | 1.05951 (18) | 0.6836 (3) | 0.92725 (17) | 0.0359 (5) | |
C21 | 1.0676 (2) | 0.5854 (4) | 1.00695 (19) | 0.0453 (6) | |
H21 | 1.0286 | 0.4729 | 1.0005 | 0.054* | |
C22 | 1.1336 (2) | 0.6541 (5) | 1.0960 (2) | 0.0557 (7) | |
H22 | 1.1379 | 0.5884 | 1.1495 | 0.067* | |
C23 | 1.1925 (2) | 0.8162 (5) | 1.1073 (2) | 0.0600 (8) | |
H23 | 1.2366 | 0.8609 | 1.1680 | 0.072* | |
C24 | 1.1866 (2) | 0.9139 (5) | 1.0285 (2) | 0.0587 (7) | |
H24 | 1.2271 | 1.0242 | 1.0356 | 0.070* | |
C25 | 1.1202 (2) | 0.8473 (4) | 0.9390 (2) | 0.0471 (6) | |
H25 | 1.1162 | 0.9134 | 0.8857 | 0.057* | |
C26 | 0.78715 (19) | 0.2237 (4) | 0.63967 (16) | 0.0380 (5) | |
C27 | 0.7611 (2) | 0.4255 (5) | 0.6230 (2) | 0.0486 (6) | |
H27 | 0.8081 | 0.5200 | 0.6270 | 0.058* | |
C28 | 0.6640 (3) | 0.4843 (6) | 0.6006 (3) | 0.0656 (9) | |
H28 | 0.6465 | 0.6187 | 0.5886 | 0.079* | |
C29 | 0.5940 (2) | 0.3490 (6) | 0.5957 (3) | 0.0699 (10) | |
H29 | 0.5294 | 0.3901 | 0.5807 | 0.084* | |
C30 | 0.6209 (2) | 0.1490 (6) | 0.6135 (2) | 0.0645 (9) | |
H30 | 0.5737 | 0.0551 | 0.6100 | 0.077* | |
C31 | 0.7164 (2) | 0.0883 (5) | 0.6361 (2) | 0.0511 (7) | |
H31 | 0.7336 | −0.0460 | 0.6492 | 0.061* | |
N1 | 0.76087 (15) | 0.1169 (3) | 0.42650 (14) | 0.0342 (4) | |
N2 | 0.88766 (16) | 0.1595 (3) | 0.66968 (14) | 0.0367 (4) | |
O1 | 0.85721 (15) | 0.3700 (3) | 0.41335 (14) | 0.0592 (6) | |
O2 | 0.71522 (18) | −0.1839 (3) | 0.46666 (16) | 0.0608 (6) | |
O3 | 0.89191 (14) | −0.0499 (3) | 0.64921 (12) | 0.0442 (4) | |
O4 | 1.11759 (13) | 0.3476 (3) | 0.67218 (12) | 0.0419 (4) | |
O5 | 1.28173 (14) | 0.2528 (3) | 0.77001 (14) | 0.0501 (5) | |
O6 | 1.23964 (13) | 0.2227 (3) | 0.88938 (12) | 0.0419 (4) | |
O7 | 1.02692 (15) | 0.5529 (3) | 0.77010 (13) | 0.0429 (4) | |
Br1 | 0.35138 (3) | 0.41736 (8) | 0.14395 (3) | 0.1005 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0417 (13) | 0.0400 (13) | 0.0428 (13) | −0.0072 (11) | 0.0157 (11) | −0.0124 (11) |
C2 | 0.0489 (15) | 0.0478 (14) | 0.0581 (17) | 0.0043 (12) | 0.0228 (13) | −0.0084 (13) |
C3 | 0.0343 (14) | 0.0731 (19) | 0.0541 (18) | 0.0086 (13) | 0.0158 (13) | −0.0138 (14) |
C4 | 0.0374 (14) | 0.0683 (19) | 0.0611 (18) | −0.0091 (13) | 0.0177 (13) | −0.0319 (15) |
C5 | 0.0384 (13) | 0.0423 (12) | 0.0578 (17) | −0.0065 (11) | 0.0222 (12) | −0.0192 (12) |
C6 | 0.0352 (12) | 0.0398 (12) | 0.0353 (12) | −0.0065 (9) | 0.0185 (10) | −0.0070 (9) |
C7 | 0.0558 (15) | 0.0311 (11) | 0.0400 (13) | −0.0054 (11) | 0.0244 (11) | −0.0081 (10) |
C8 | 0.0340 (12) | 0.0461 (13) | 0.0338 (12) | −0.0050 (10) | 0.0153 (10) | −0.0001 (10) |
C9 | 0.0329 (12) | 0.0425 (12) | 0.0357 (12) | 0.0009 (9) | 0.0161 (10) | 0.0006 (10) |
C10 | 0.0530 (14) | 0.0315 (11) | 0.0431 (14) | 0.0070 (11) | 0.0218 (11) | 0.0019 (10) |
C11 | 0.0334 (11) | 0.0352 (11) | 0.0328 (11) | 0.0030 (9) | 0.0149 (9) | 0.0044 (9) |
C12 | 0.0341 (12) | 0.0363 (11) | 0.0350 (12) | −0.0004 (9) | 0.0158 (10) | 0.0014 (9) |
C13 | 0.0381 (12) | 0.0349 (11) | 0.0329 (11) | 0.0004 (9) | 0.0181 (10) | 0.0045 (9) |
C14 | 0.0393 (11) | 0.0383 (11) | 0.0316 (11) | −0.0032 (10) | 0.0127 (9) | −0.0022 (10) |
C15 | 0.0358 (11) | 0.0427 (12) | 0.0385 (12) | −0.0072 (10) | 0.0142 (10) | 0.0027 (11) |
C16 | 0.0345 (13) | 0.0587 (15) | 0.0402 (13) | 0.0000 (11) | 0.0166 (11) | 0.0047 (12) |
C17 | 0.076 (2) | 0.0624 (19) | 0.080 (2) | 0.0156 (18) | 0.0458 (19) | 0.0102 (17) |
C18 | 0.0406 (18) | 0.111 (3) | 0.064 (2) | −0.0090 (18) | 0.0140 (16) | −0.008 (2) |
C19 | 0.0424 (14) | 0.0470 (14) | 0.0435 (14) | 0.0091 (11) | 0.0227 (12) | 0.0013 (11) |
C20 | 0.0380 (12) | 0.0380 (12) | 0.0371 (12) | 0.0077 (10) | 0.0219 (10) | 0.0018 (10) |
C21 | 0.0496 (15) | 0.0464 (14) | 0.0456 (15) | 0.0005 (12) | 0.0268 (13) | 0.0069 (11) |
C22 | 0.0602 (18) | 0.0670 (18) | 0.0401 (15) | 0.0136 (15) | 0.0234 (14) | 0.0121 (13) |
C23 | 0.0455 (16) | 0.077 (2) | 0.0481 (17) | 0.0061 (15) | 0.0141 (13) | −0.0170 (15) |
C24 | 0.0553 (16) | 0.0568 (16) | 0.0696 (19) | −0.0134 (15) | 0.0337 (14) | −0.0139 (16) |
C25 | 0.0585 (17) | 0.0401 (13) | 0.0524 (16) | −0.0017 (11) | 0.0338 (14) | 0.0016 (11) |
C26 | 0.0387 (13) | 0.0487 (13) | 0.0282 (11) | −0.0048 (10) | 0.0167 (10) | −0.0032 (10) |
C27 | 0.0428 (13) | 0.0461 (14) | 0.0596 (16) | 0.0018 (12) | 0.0259 (12) | 0.0012 (13) |
C28 | 0.0530 (19) | 0.071 (2) | 0.078 (2) | 0.0156 (15) | 0.0347 (17) | 0.0065 (17) |
C29 | 0.0366 (15) | 0.108 (3) | 0.067 (2) | 0.0044 (16) | 0.0253 (15) | −0.008 (2) |
C30 | 0.0486 (18) | 0.088 (3) | 0.065 (2) | −0.0179 (17) | 0.0339 (16) | −0.0119 (18) |
C31 | 0.0508 (16) | 0.0582 (16) | 0.0496 (16) | −0.0155 (13) | 0.0278 (13) | −0.0062 (13) |
N1 | 0.0341 (10) | 0.0343 (9) | 0.0339 (10) | −0.0038 (7) | 0.0155 (8) | −0.0032 (8) |
N2 | 0.0378 (10) | 0.0365 (10) | 0.0355 (10) | −0.0027 (8) | 0.0166 (8) | −0.0001 (8) |
O1 | 0.0442 (10) | 0.0710 (13) | 0.0481 (11) | −0.0187 (9) | 0.0092 (8) | 0.0213 (10) |
O2 | 0.0768 (15) | 0.0417 (10) | 0.0591 (13) | −0.0238 (10) | 0.0274 (12) | −0.0086 (9) |
O3 | 0.0540 (10) | 0.0345 (8) | 0.0416 (9) | 0.0038 (8) | 0.0198 (8) | 0.0092 (7) |
O4 | 0.0365 (9) | 0.0575 (11) | 0.0325 (8) | −0.0067 (8) | 0.0167 (7) | −0.0015 (7) |
O5 | 0.0431 (11) | 0.0668 (12) | 0.0457 (10) | 0.0046 (9) | 0.0250 (9) | 0.0085 (9) |
O6 | 0.0403 (10) | 0.0494 (10) | 0.0364 (9) | 0.0036 (8) | 0.0180 (8) | 0.0072 (7) |
O7 | 0.0575 (11) | 0.0388 (9) | 0.0350 (9) | 0.0079 (8) | 0.0235 (8) | 0.0037 (7) |
Br1 | 0.0491 (2) | 0.1229 (4) | 0.0909 (3) | 0.0303 (2) | −0.00047 (17) | −0.0247 (3) |
C1—C2 | 1.379 (4) | C16—O6 | 1.421 (3) |
C1—C6 | 1.380 (4) | C16—O5 | 1.423 (3) |
C1—H1 | 0.9300 | C16—C18 | 1.502 (4) |
C2—C3 | 1.372 (4) | C16—C17 | 1.513 (5) |
C2—H2 | 0.9300 | C17—H17A | 0.9600 |
C3—C4 | 1.377 (5) | C17—H17B | 0.9600 |
C3—Br1 | 1.878 (3) | C17—H17C | 0.9600 |
C4—C5 | 1.384 (4) | C18—H18A | 0.9600 |
C4—H4 | 0.9300 | C18—H18B | 0.9600 |
C5—C6 | 1.380 (3) | C18—H18C | 0.9600 |
C5—H5 | 0.9300 | C19—O7 | 1.433 (3) |
C6—N1 | 1.425 (3) | C19—C20 | 1.505 (4) |
C7—O2 | 1.198 (3) | C19—H19A | 0.9700 |
C7—N1 | 1.393 (3) | C19—H19B | 0.9700 |
C7—C10 | 1.527 (4) | C20—C21 | 1.378 (3) |
C8—O1 | 1.199 (3) | C20—C25 | 1.382 (4) |
C8—N1 | 1.405 (3) | C21—C22 | 1.376 (4) |
C8—C9 | 1.503 (3) | C21—H21 | 0.9300 |
C9—C10 | 1.513 (4) | C22—C23 | 1.359 (5) |
C9—C11 | 1.538 (3) | C22—H22 | 0.9300 |
C9—H9 | 0.9800 | C23—C24 | 1.375 (5) |
C10—O3 | 1.443 (3) | C23—H23 | 0.9300 |
C10—H10 | 0.9800 | C24—C25 | 1.377 (4) |
C11—N2 | 1.464 (3) | C24—H24 | 0.9300 |
C11—C12 | 1.509 (3) | C25—H25 | 0.9300 |
C11—H11 | 0.9800 | C26—C31 | 1.379 (4) |
C12—O4 | 1.442 (3) | C26—C27 | 1.395 (4) |
C12—C13 | 1.524 (3) | C26—N2 | 1.427 (3) |
C12—H12 | 0.9800 | C27—C28 | 1.392 (4) |
C13—O7 | 1.411 (3) | C27—H27 | 0.9300 |
C13—C14 | 1.520 (3) | C28—C29 | 1.364 (5) |
C13—H13 | 0.9800 | C28—H28 | 0.9300 |
C14—O6 | 1.420 (3) | C29—C30 | 1.386 (6) |
C14—C15 | 1.529 (3) | C29—H29 | 0.9300 |
C14—H14 | 0.9800 | C30—C31 | 1.374 (4) |
C15—O5 | 1.400 (3) | C30—H30 | 0.9300 |
C15—O4 | 1.413 (3) | C31—H31 | 0.9300 |
C15—H15 | 0.9800 | N2—O3 | 1.444 (3) |
C2—C1—C6 | 119.5 (2) | O6—C16—C17 | 108.6 (2) |
C2—C1—H1 | 120.2 | O5—C16—C17 | 109.3 (3) |
C6—C1—H1 | 120.2 | C18—C16—C17 | 112.5 (3) |
C3—C2—C1 | 120.0 (3) | C16—C17—H17A | 109.5 |
C3—C2—H2 | 120.0 | C16—C17—H17B | 109.5 |
C1—C2—H2 | 120.0 | H17A—C17—H17B | 109.5 |
C2—C3—C4 | 120.9 (3) | C16—C17—H17C | 109.5 |
C2—C3—Br1 | 119.0 (2) | H17A—C17—H17C | 109.5 |
C4—C3—Br1 | 120.2 (2) | H17B—C17—H17C | 109.5 |
C3—C4—C5 | 119.3 (3) | C16—C18—H18A | 109.5 |
C3—C4—H4 | 120.4 | C16—C18—H18B | 109.5 |
C5—C4—H4 | 120.4 | H18A—C18—H18B | 109.5 |
C6—C5—C4 | 119.9 (3) | C16—C18—H18C | 109.5 |
C6—C5—H5 | 120.1 | H18A—C18—H18C | 109.5 |
C4—C5—H5 | 120.1 | H18B—C18—H18C | 109.5 |
C1—C6—C5 | 120.4 (2) | O7—C19—C20 | 114.1 (2) |
C1—C6—N1 | 119.1 (2) | O7—C19—H19A | 108.7 |
C5—C6—N1 | 120.5 (2) | C20—C19—H19A | 108.7 |
O2—C7—N1 | 125.6 (3) | O7—C19—H19B | 108.7 |
O2—C7—C10 | 126.5 (2) | C20—C19—H19B | 108.7 |
N1—C7—C10 | 107.9 (2) | H19A—C19—H19B | 107.6 |
O1—C8—N1 | 123.9 (2) | C21—C20—C25 | 118.8 (2) |
O1—C8—C9 | 126.9 (2) | C21—C20—C19 | 121.0 (2) |
N1—C8—C9 | 109.2 (2) | C25—C20—C19 | 120.2 (2) |
C8—C9—C10 | 104.74 (19) | C22—C21—C20 | 119.8 (3) |
C8—C9—C11 | 110.7 (2) | C22—C21—H21 | 120.1 |
C10—C9—C11 | 103.35 (19) | C20—C21—H21 | 120.1 |
C8—C9—H9 | 112.5 | C23—C22—C21 | 121.2 (3) |
C10—C9—H9 | 112.5 | C23—C22—H22 | 119.4 |
C11—C9—H9 | 112.5 | C21—C22—H22 | 119.4 |
O3—C10—C9 | 106.3 (2) | C22—C23—C24 | 119.7 (3) |
O3—C10—C7 | 110.5 (2) | C22—C23—H23 | 120.2 |
C9—C10—C7 | 105.72 (19) | C24—C23—H23 | 120.2 |
O3—C10—H10 | 111.4 | C25—C24—C23 | 119.5 (3) |
C9—C10—H10 | 111.4 | C25—C24—H24 | 120.2 |
C7—C10—H10 | 111.4 | C23—C24—H24 | 120.2 |
N2—C11—C12 | 107.55 (18) | C24—C25—C20 | 120.9 (3) |
N2—C11—C9 | 105.52 (19) | C24—C25—H25 | 119.5 |
C12—C11—C9 | 112.38 (19) | C20—C25—H25 | 119.5 |
N2—C11—H11 | 110.4 | C31—C26—C27 | 118.8 (3) |
C12—C11—H11 | 110.4 | C31—C26—N2 | 119.8 (2) |
C9—C11—H11 | 110.4 | C27—C26—N2 | 121.1 (2) |
O4—C12—C11 | 108.86 (18) | C28—C27—C26 | 119.5 (3) |
O4—C12—C13 | 103.47 (18) | C28—C27—H27 | 120.3 |
C11—C12—C13 | 114.83 (19) | C26—C27—H27 | 120.3 |
O4—C12—H12 | 109.8 | C29—C28—C27 | 121.3 (3) |
C11—C12—H12 | 109.8 | C29—C28—H28 | 119.3 |
C13—C12—H12 | 109.8 | C27—C28—H28 | 119.3 |
O7—C13—C14 | 110.6 (2) | C28—C29—C30 | 118.8 (3) |
O7—C13—C12 | 108.39 (18) | C28—C29—H29 | 120.6 |
C14—C13—C12 | 100.91 (18) | C30—C29—H29 | 120.6 |
O7—C13—H13 | 112.1 | C31—C30—C29 | 120.6 (3) |
C14—C13—H13 | 112.1 | C31—C30—H30 | 119.7 |
C12—C13—H13 | 112.1 | C29—C30—H30 | 119.7 |
O6—C14—C13 | 109.06 (19) | C30—C31—C26 | 120.9 (3) |
O6—C14—C15 | 103.8 (2) | C30—C31—H31 | 119.5 |
C13—C14—C15 | 103.82 (17) | C26—C31—H31 | 119.5 |
O6—C14—H14 | 113.1 | C7—N1—C8 | 111.6 (2) |
C13—C14—H14 | 113.1 | C7—N1—C6 | 124.2 (2) |
C15—C14—H14 | 113.1 | C8—N1—C6 | 124.1 (2) |
O5—C15—O4 | 111.0 (2) | C26—N2—O3 | 111.51 (19) |
O5—C15—C14 | 105.81 (19) | C26—N2—C11 | 120.00 (19) |
O4—C15—C14 | 107.62 (18) | O3—N2—C11 | 103.42 (17) |
O5—C15—H15 | 110.8 | N2—O3—C10 | 106.78 (17) |
O4—C15—H15 | 110.8 | C15—O4—C12 | 106.98 (17) |
C14—C15—H15 | 110.8 | C15—O5—C16 | 109.83 (19) |
O6—C16—O5 | 105.7 (2) | C14—O6—C16 | 108.42 (18) |
O6—C16—C18 | 110.7 (2) | C13—O7—C19 | 114.50 (18) |
O5—C16—C18 | 109.9 (3) | ||
C6—C1—C2—C3 | −0.2 (4) | C19—C20—C25—C24 | 177.0 (3) |
C1—C2—C3—C4 | 0.7 (5) | C31—C26—C27—C28 | −1.9 (4) |
C1—C2—C3—Br1 | 179.9 (2) | N2—C26—C27—C28 | −175.4 (3) |
C2—C3—C4—C5 | −0.5 (5) | C26—C27—C28—C29 | 0.9 (5) |
Br1—C3—C4—C5 | −179.7 (2) | C27—C28—C29—C30 | −0.1 (6) |
C3—C4—C5—C6 | −0.3 (5) | C28—C29—C30—C31 | 0.3 (6) |
C2—C1—C6—C5 | −0.5 (4) | C29—C30—C31—C26 | −1.4 (5) |
C2—C1—C6—N1 | −178.4 (2) | C27—C26—C31—C30 | 2.2 (4) |
C4—C5—C6—C1 | 0.8 (4) | N2—C26—C31—C30 | 175.7 (3) |
C4—C5—C6—N1 | 178.6 (2) | O2—C7—N1—C8 | −175.9 (2) |
O1—C8—C9—C10 | −172.5 (3) | C10—C7—N1—C8 | 5.6 (3) |
N1—C8—C9—C10 | 9.1 (3) | O2—C7—N1—C6 | 8.6 (4) |
O1—C8—C9—C11 | 76.7 (3) | C10—C7—N1—C6 | −169.94 (19) |
N1—C8—C9—C11 | −101.7 (2) | O1—C8—N1—C7 | 172.1 (2) |
C8—C9—C10—O3 | −123.0 (2) | C9—C8—N1—C7 | −9.4 (3) |
C11—C9—C10—O3 | −7.1 (2) | O1—C8—N1—C6 | −12.3 (4) |
C8—C9—C10—C7 | −5.5 (2) | C9—C8—N1—C6 | 166.1 (2) |
C11—C9—C10—C7 | 110.4 (2) | C1—C6—N1—C7 | 134.2 (2) |
O2—C7—C10—O3 | −63.6 (3) | C5—C6—N1—C7 | −43.7 (3) |
N1—C7—C10—O3 | 114.9 (2) | C1—C6—N1—C8 | −40.8 (3) |
O2—C7—C10—C9 | −178.2 (3) | C5—C6—N1—C8 | 141.3 (2) |
N1—C7—C10—C9 | 0.3 (2) | C31—C26—N2—O3 | 27.9 (3) |
C8—C9—C11—N2 | 95.2 (2) | C27—C26—N2—O3 | −158.7 (2) |
C10—C9—C11—N2 | −16.4 (2) | C31—C26—N2—C11 | 149.0 (2) |
C8—C9—C11—C12 | −147.9 (2) | C27—C26—N2—C11 | −37.7 (3) |
C10—C9—C11—C12 | 100.5 (2) | C12—C11—N2—C26 | 148.6 (2) |
N2—C11—C12—O4 | −179.02 (17) | C9—C11—N2—C26 | −91.2 (2) |
C9—C11—C12—O4 | 65.3 (2) | C12—C11—N2—O3 | −86.4 (2) |
N2—C11—C12—C13 | −63.6 (2) | C9—C11—N2—O3 | 33.8 (2) |
C9—C11—C12—C13 | −179.3 (2) | C26—N2—O3—C10 | 91.0 (2) |
O4—C12—C13—O7 | 75.3 (2) | C11—N2—O3—C10 | −39.3 (2) |
C11—C12—C13—O7 | −43.2 (3) | C9—C10—O3—N2 | 28.7 (2) |
O4—C12—C13—C14 | −40.9 (2) | C7—C10—O3—N2 | −85.5 (2) |
C11—C12—C13—C14 | −159.34 (19) | O5—C15—O4—C12 | 95.9 (2) |
O7—C13—C14—O6 | 163.81 (18) | C14—C15—O4—C12 | −19.5 (3) |
C12—C13—C14—O6 | −81.6 (2) | C11—C12—O4—C15 | 160.8 (2) |
O7—C13—C14—C15 | −86.0 (2) | C13—C12—O4—C15 | 38.2 (2) |
C12—C13—C14—C15 | 28.5 (2) | O4—C15—O5—C16 | −120.5 (2) |
O6—C14—C15—O5 | −11.6 (2) | C14—C15—O5—C16 | −4.1 (3) |
C13—C14—C15—O5 | −125.6 (2) | O6—C16—O5—C15 | 18.4 (3) |
O6—C14—C15—O4 | 107.1 (2) | C18—C16—O5—C15 | −101.0 (3) |
C13—C14—C15—O4 | −6.9 (3) | C17—C16—O5—C15 | 135.0 (3) |
O7—C19—C20—C21 | −118.0 (3) | C13—C14—O6—C16 | 133.4 (2) |
O7—C19—C20—C25 | 64.0 (3) | C15—C14—O6—C16 | 23.3 (2) |
C25—C20—C21—C22 | 1.6 (4) | O5—C16—O6—C14 | −26.3 (3) |
C19—C20—C21—C22 | −176.4 (2) | C18—C16—O6—C14 | 92.6 (3) |
C20—C21—C22—C23 | −1.0 (4) | C17—C16—O6—C14 | −143.4 (2) |
C21—C22—C23—C24 | −0.1 (5) | C14—C13—O7—C19 | −109.0 (2) |
C22—C23—C24—C25 | 0.6 (5) | C12—C13—O7—C19 | 141.2 (2) |
C23—C24—C25—C20 | 0.0 (4) | C20—C19—O7—C13 | 70.5 (3) |
C21—C20—C25—C24 | −1.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O2i | 0.93 | 2.46 | 3.273 (3) | 145 |
C5—H5···O5ii | 0.93 | 2.52 | 3.198 (3) | 130 |
C9—H9···O1ii | 0.98 | 2.58 | 3.418 (3) | 144 |
C19—H19B···O3i | 0.97 | 2.58 | 3.360 (3) | 137 |
C17—H17b···Cg1iii | 0.96 | 2.86 | 3.720 (4) | 150 |
C21—H21···Cg2iv | 0.93 | 2.67 | 3.559 (7) | 160 |
Symmetry codes: (i) x, y+1, z; (ii) −x+2, y−1/2, −z+1; (iii) −x, y−1/2, −z+1; (iv) −x, y−1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C31H29BrN2O7 |
Mr | 621.47 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 293 |
a, b, c (Å) | 15.0680 (12), 6.6801 (5), 15.8550 (12) |
β (°) | 117.578 (2) |
V (Å3) | 1414.57 (19) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.51 |
Crystal size (mm) | 0.3 × 0.2 × 0.2 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker 2004) |
Tmin, Tmax | 0.734, 0.740 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20450, 9003, 5502 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.738 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.138, 1.00 |
No. of reflections | 9003 |
No. of parameters | 372 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.66, −0.38 |
Absolute structure | Flack (1983), 3886 Friedel pairs |
Absolute structure parameter | −0.001 (8) |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O2i | 0.93 | 2.46 | 3.273 (3) | 145.4 |
C5—H5···O5ii | 0.93 | 2.52 | 3.198 (3) | 130.4 |
C9—H9···O1ii | 0.98 | 2.58 | 3.418 (3) | 143.5 |
C19—H19B···O3i | 0.97 | 2.58 | 3.360 (3) | 137.2 |
C17—H17b···Cg1iii | 0.96 | 2.86 | 3.720 (4) | 150 |
C21—H21···Cg2iv | 0.93 | 2.67 | 3.559 (7) | 160 |
Symmetry codes: (i) x, y+1, z; (ii) −x+2, y−1/2, −z+1; (iii) −x, y−1/2, −z+1; (iv) −x, y−1/2, −z. |
Isoxazolidines are potential precursors for biologically important compounds such as amino sugars (Ali et al., 1988), alkaloids (Goti et al., 1997), and exhibit antibacterial and antifungal activities (Kumar et al., 2003). The stereochemistry, such as regioselectivity and enantioselectivity, of heterocyclic isoxazole compounds (Huisgen, 1984) can be studied by 1,3-dipolar cycloaddition reactions. In view of these important properties, the crystal structure of the title compound, (I), has been determined.
A perspective view of compound (I) with the atom-numbering scheme is shown in Fig. 1. The dihedral angle between the phenyl rings C1—C6 and C20—C25, and, C20—C25 and C26—C31, C1—C6 and C26—C31 are 62.4 (1), 75.9 (1) and 42.1 (1)°, respectively.
The five membered isoxazolidine ring (C9-C1,O3,N2) adopts a twisted conformation On O3 and N2 with a pseudo-twofold axis passing through C11-C9 bond. The other five membered tetrahydrofuran, dioxolone and pyrrole rings adopt envelope conformation on C12, O6 and C8 respectively. The puckering parameters (Cremer & Pople, 1975) and the lowest displacement asymmetry parameters (Nardelli, 1983) as follows: for the isoxazolidine ring q2 = 0.353 (1) Å, ϕ = 26.0 (1)°, ΔS(N2) is 9.6 (1)° and Δ2(C9) is 7.4 (1)°, for the tetrahydrofuran ring q2 = 0.395 (1) Å, ϕ = 313.0 (1)°, ΔS(C12) is 6.6 (1)° and Δ2(C15) is 11.2 (1)°, for the dioxolone ring q2 = 0.232 (1) Å, ϕ = 295.8 (1)°, ΔS(O6) is 5.3 (1)° and Δ2(C15) is 6.2 (1)° and for the pyrrole ring q2 = 0.085 (1) Å, ϕ = 140.0 (1)°, ΔS(C8) is 0.2 (1)° and Δ2(C7) is 4.5 (1)°.
The crystal structure is stabilized by intermolecular C—H···O hydrogen bonds (Table 1; Fig. 2). The crystal structure is further stabilized by C—H···π interactions involing rings C17—H17B···Cg1 and C21—H21···Cg2 (Cg1 and Cg2 denote the centroid of the C1—C6 and C20—C25 phenyl rings).