Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103018584/ty1001sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270103018584/ty1001Isup2.hkl |
CCDC reference: 224673
A mixture of 4-(4-methoxybenzoyl)-2-[(Z)-methoxycarbonylmethylene]-5- (4-methoxyphenyl)-2,3-dihydro-3-furanone (2.213 g, 5 mmol) and ethylamine (70% in water; 0.322 g, 0.40 ml, 5 mmol) in benzene (25 ml) was refluxed for 30 min. The solid remaining after evaporation of the solvent was recrystallized from ethanol to give white crystals of (I) (yield: 1.54 g, 70%; m.p. 435 K). Solvents were dried by refluxing with the appropriate drying agent and were distilled before use. Melting points were determined on an Electrothermal 9200 apparatus and are uncorrected. Elemental analysis was performed with a Carlo-Erba 1108 Elemental Analyzer. The FT—IR spectrum was measured on a Jasco Plus Model 460 spectrometer. The 1H and 13C NMR spectra were obtained on a Gemini-Varian 200 MHz instrument. The chemical shifts are reported from tetramethylsilane ?CDCl3 below. Spectroscopic analysis: FT—IR (KBr pellet, ν, cm−1): 3212.34 (broad OH), 1733.69 (C12═O), 1678.69 (C8═O), 1674.39 (C4═O), 1251.58 (C12—O—C13); 1H NMR (CDCl3, δ, p.p.m.): 1.095–1.167 (s, 3H, CH3), 2.940–3.211 (q, 2H, CH2C═O), 3.300–3.604 (q, 2H, NCH2), 3.884, 3.780, 3.797 (s, 9H, OCH3), 5.942 (s, 1H, OH), 6.731–7.700 (m, 8H, Ar—H); 13C NMR (CDCl3, δ, p.p.m.): 17.474 (C7), 40.230 (C11), 42.588 (C6), 53.904, 57.216 (C13, C10, C9), 90.746 (C5), 112.392–164.865 (C═C, arom. and aliph.), 182.945 (C12═O), 188.924 (C8═O), 196.037 (C4═O). Analysis calculated for C24H25NO7: C 65.59, N 3.19, H 5.73%; found: C 65.41, N 3.30, H 5.72%.
The H atoms were introduced at calculated positions and refined as riding atoms, with bond lengths of 0.82 (O—H), 0.93 (C—H aromatic), 0.96 (CH3) and 0.97 Å (CH2), and with Uiso(H) = 1.2Ueq(parent atom) or 1.5Ueq(methyl C and hydroxyl O).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST (Nardelli, 1995) and WinGX (Farrugia, 1999).
C24H25NO7 | Z = 2 |
Mr = 439.45 | F(000) = 464 |
Triclinic, P1 | Dx = 1.292 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.160 (5) Å | Cell parameters from 2644 reflections |
b = 10.785 (5) Å | θ = 4.6–49.1° |
c = 11.942 (5) Å | µ = 0.10 mm−1 |
α = 66.369 (5)° | T = 293 K |
β = 75.928 (5)° | Block, colourless |
γ = 72.005 (5)° | 0.52 × 0.26 × 0.20 mm |
V = 1129.4 (9) Å3 |
Siemens SMART CCD area-detector diffractometer | 6035 independent reflections |
Radiation source: fine-focus sealed tube | 4369 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.000 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 2.3° |
ω scans | h = −13→13 |
Absorption correction: part of the refinement model (ΔF) [Parkin et al., 1995; cubic fit to sin(θ)/λ with 24 parameters] | k = −14→11 |
Tmin = 0.952, Tmax = 0.981 | l = −15→15 |
6035 measured reflections |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0372P)2 + 0.2621P] where P = (Fo2 + 2Fc2)/3 |
6035 reflections | (Δ/σ)max = 0.002 |
577 parameters | Δρmax = 0.22 e Å−3 |
3 restraints | Δρmin = −0.19 e Å−3 |
C24H25NO7 | γ = 72.005 (5)° |
Mr = 439.45 | V = 1129.4 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.160 (5) Å | Mo Kα radiation |
b = 10.785 (5) Å | µ = 0.10 mm−1 |
c = 11.942 (5) Å | T = 293 K |
α = 66.369 (5)° | 0.52 × 0.26 × 0.20 mm |
β = 75.928 (5)° |
Siemens SMART CCD area-detector diffractometer | 6035 independent reflections |
Absorption correction: part of the refinement model (ΔF) [Parkin et al., 1995; cubic fit to sin(θ)/λ with 24 parameters] | 4369 reflections with I > 2σ(I) |
Tmin = 0.952, Tmax = 0.981 | Rint = 0.000 |
6035 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 3 restraints |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.22 e Å−3 |
6035 reflections | Δρmin = −0.19 e Å−3 |
577 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
O1 | 1.3476 (3) | 1.1448 (3) | 0.5652 (3) | 0.0500 (12) | |
O2 | 1.2440 (4) | 0.9979 (3) | 0.4530 (3) | 0.0533 (13) | |
O3 | 1.1016 (3) | 0.6744 (3) | 0.7612 (2) | 0.0462 (11) | |
O4 | 1.5072 (4) | 0.5016 (4) | 0.3256 (3) | 0.0608 (14) | |
O5 | 1.0551 (5) | 0.5846 (4) | 1.2672 (3) | 0.0824 (18) | |
O6 | 0.9148 (4) | 1.1505 (5) | 0.6855 (3) | 0.0852 (16) | |
O7 | 0.8889 (4) | 1.2756 (4) | 0.4922 (3) | 0.0758 (16) | |
N1 | 1.1913 (4) | 1.0449 (4) | 0.7364 (3) | 0.0355 (11) | |
C1 | 1.2207 (5) | 1.1041 (5) | 0.6015 (4) | 0.0379 (14) | |
C2 | 1.2259 (4) | 0.9836 (5) | 0.5615 (4) | 0.0343 (14) | |
C3 | 1.2006 (4) | 0.8679 (4) | 0.6731 (3) | 0.0339 (14) | |
C4 | 1.1789 (4) | 0.9147 (4) | 0.7716 (4) | 0.0317 (12) | |
C5 | 1.1827 (4) | 0.7375 (4) | 0.6789 (3) | 0.0314 (12) | |
C6 | 1.2661 (5) | 0.6782 (4) | 0.5826 (4) | 0.0365 (14) | |
C7 | 1.3995 (5) | 0.6974 (5) | 0.5294 (4) | 0.0440 (16) | |
C8 | 1.4779 (5) | 0.6354 (5) | 0.4455 (5) | 0.0507 (17) | |
C9 | 1.4232 (5) | 0.5564 (5) | 0.4113 (4) | 0.0419 (14) | |
C10 | 1.2906 (6) | 0.5367 (5) | 0.4633 (4) | 0.0491 (17) | |
C11 | 1.2127 (5) | 0.5987 (5) | 0.5469 (4) | 0.0447 (17) | |
C12 | 1.4666 (7) | 0.3955 (7) | 0.3072 (5) | 0.070 (2) | |
C13 | 1.1453 (4) | 0.8337 (4) | 0.9039 (3) | 0.0323 (12) | |
C14 | 1.2361 (6) | 0.7093 (6) | 0.9591 (4) | 0.064 (2) | |
C15 | 1.2034 (7) | 0.6294 (7) | 1.0799 (5) | 0.079 (2) | |
C16 | 1.0796 (7) | 0.6740 (6) | 1.1493 (4) | 0.059 (2) | |
C17 | 0.9896 (6) | 0.7974 (5) | 1.0957 (4) | 0.0488 (18) | |
C18 | 1.0233 (5) | 0.8763 (5) | 0.9726 (4) | 0.0414 (16) | |
C19 | 0.9268 (9) | 0.6230 (7) | 1.3403 (5) | 0.095 (3) | |
C20 | 1.1851 (5) | 1.1227 (5) | 0.8153 (4) | 0.0466 (17) | |
C21 | 1.3161 (8) | 1.0936 (11) | 0.8606 (9) | 0.138 (5) | |
C22 | 1.1088 (5) | 1.2331 (5) | 0.5471 (4) | 0.0468 (17) | |
C23 | 0.9622 (6) | 1.2120 (5) | 0.5840 (5) | 0.0490 (17) | |
C24 | 0.7445 (8) | 1.2684 (10) | 0.5202 (7) | 0.111 (3) | |
O8 | 1.0135 (4) | 0.4316 (3) | 0.8427 (3) | 0.0528 (11) | |
O9 | 0.8557 (4) | 0.5556 (3) | 0.6328 (3) | 0.0630 (13) | |
O10 | 0.5337 (3) | 0.8905 (4) | 0.6839 (3) | 0.0520 (11) | |
O11 | 0.9333 (4) | 1.0830 (4) | 0.1876 (3) | 0.0578 (13) | |
O12 | 0.5278 (4) | 1.1040 (4) | 1.0837 (3) | 0.0629 (14) | |
O13 | 0.5754 (5) | 0.4318 (5) | 0.9933 (4) | 0.0804 (17) | |
O14 | 0.6022 (4) | 0.3825 (4) | 0.8247 (3) | 0.0643 (14) | |
N2 | 0.8153 (4) | 0.5672 (3) | 0.9307 (3) | 0.0381 (13) | |
C25 | 0.8699 (5) | 0.4819 (4) | 0.8506 (4) | 0.0381 (14) | |
C26 | 0.8229 (5) | 0.5864 (5) | 0.7252 (4) | 0.0426 (16) | |
C27 | 0.7334 (4) | 0.7095 (4) | 0.7471 (3) | 0.0335 (14) | |
C28 | 0.7359 (5) | 0.6926 (4) | 0.8697 (3) | 0.0350 (14) | |
C29 | 0.6561 (5) | 0.8330 (5) | 0.6576 (4) | 0.0383 (16) | |
C30 | 0.8752 (5) | 0.8798 (5) | 0.5179 (4) | 0.0404 (16) | |
C31 | 0.9458 (5) | 0.9448 (5) | 0.4044 (4) | 0.0451 (16) | |
C32 | 0.8750 (5) | 1.0172 (5) | 0.3039 (4) | 0.0424 (16) | |
C33 | 0.7332 (5) | 1.0279 (5) | 0.3169 (4) | 0.0441 (16) | |
C34 | 0.6616 (5) | 0.9671 (5) | 0.4303 (4) | 0.0412 (16) | |
C35 | 0.7335 (5) | 0.8923 (4) | 0.5324 (3) | 0.0339 (14) | |
C36 | 1.0762 (7) | 1.0799 (8) | 0.1703 (5) | 0.091 (3) | |
C37 | 0.6748 (4) | 0.7976 (4) | 0.9262 (3) | 0.0328 (14) | |
C38 | 0.7073 (5) | 0.9271 (5) | 0.8708 (4) | 0.0396 (16) | |
C39 | 0.6577 (5) | 1.0253 (5) | 0.9263 (4) | 0.0424 (17) | |
C40 | 0.5710 (5) | 0.9981 (5) | 1.0379 (4) | 0.0447 (17) | |
C41 | 0.5345 (6) | 0.8723 (6) | 1.0933 (4) | 0.0530 (19) | |
C42 | 0.5887 (6) | 0.7721 (5) | 1.0391 (4) | 0.0487 (18) | |
C43 | 0.4237 (6) | 1.0892 (8) | 1.1906 (6) | 0.090 (3) | |
C44 | 0.8817 (6) | 0.5364 (6) | 1.0390 (4) | 0.0573 (19) | |
C45 | 0.8378 (10) | 0.4329 (8) | 1.1535 (5) | 0.102 (3) | |
C46 | 0.8054 (5) | 0.3560 (5) | 0.8969 (4) | 0.0488 (17) | |
C47 | 0.6491 (6) | 0.3937 (5) | 0.9130 (4) | 0.0528 (19) | |
C48 | 0.4503 (9) | 0.4134 (8) | 0.8326 (7) | 0.100 (3) | |
H1 | 1.41080 | 1.07740 | 0.59310 | 0.0750* | |
H7 | 1.43640 | 0.75270 | 0.55060 | 0.0530* | |
H8 | 1.56790 | 0.64730 | 0.41210 | 0.0610* | |
H10 | 1.25400 | 0.48150 | 0.44180 | 0.0600* | |
H11 | 1.12260 | 0.58690 | 0.57990 | 0.0530* | |
H12A | 1.53300 | 0.36610 | 0.24490 | 0.1060* | |
H12B | 1.37570 | 0.43220 | 0.28120 | 0.1060* | |
H12C | 1.46420 | 0.31740 | 0.38300 | 0.1060* | |
H14 | 1.32000 | 0.67940 | 0.91400 | 0.0760* | |
H15 | 1.26440 | 0.54490 | 1.11570 | 0.0950* | |
H17 | 0.90670 | 0.82840 | 1.14100 | 0.0580* | |
H18 | 0.96160 | 0.95990 | 0.93610 | 0.0500* | |
H19A | 0.92220 | 0.55140 | 1.42040 | 0.1420* | |
H19B | 0.84990 | 0.63430 | 1.30090 | 0.1420* | |
H19C | 0.92200 | 0.70910 | 1.34890 | 0.1420* | |
H20A | 1.15780 | 1.22170 | 0.76890 | 0.0560* | |
H20B | 1.11330 | 1.10040 | 0.88540 | 0.0560* | |
H21A | 1.30470 | 1.14840 | 0.91030 | 0.2070* | |
H21B | 1.38770 | 1.11660 | 0.79190 | 0.2070* | |
H21C | 1.34230 | 0.99640 | 0.90940 | 0.2070* | |
H22A | 1.11280 | 1.30660 | 0.57240 | 0.0560* | |
H22B | 1.12970 | 1.26420 | 0.45780 | 0.0560* | |
H24A | 0.69910 | 1.32300 | 0.44800 | 0.1670* | |
H24B | 0.69870 | 1.30420 | 0.58520 | 0.1670* | |
H24C | 0.73950 | 1.17320 | 0.54610 | 0.1670* | |
H8A | 1.05090 | 0.49690 | 0.81860 | 0.0790* | |
H30 | 0.92400 | 0.82720 | 0.58500 | 0.0480* | |
H31 | 1.04060 | 0.93940 | 0.39620 | 0.0540* | |
H33 | 0.68590 | 1.07660 | 0.24850 | 0.0530* | |
H34 | 0.56610 | 0.97580 | 0.43890 | 0.0490* | |
H36A | 1.10520 | 1.12900 | 0.08510 | 0.1370* | |
H36B | 1.12950 | 0.98490 | 0.19350 | 0.1370* | |
H36C | 1.09140 | 1.12360 | 0.22050 | 0.1370* | |
H38 | 0.76360 | 0.94760 | 0.79480 | 0.0470* | |
H39 | 0.68240 | 1.11040 | 0.88860 | 0.0510* | |
H41 | 0.47370 | 0.85470 | 1.16690 | 0.0640* | |
H42 | 0.56700 | 0.68560 | 1.07900 | 0.0590* | |
H43A | 0.40250 | 1.16940 | 1.21390 | 0.1340* | |
H43B | 0.45830 | 1.00710 | 1.25730 | 0.1340* | |
H43C | 0.34050 | 1.08110 | 1.17200 | 0.1340* | |
H44A | 0.98180 | 0.50590 | 1.01820 | 0.0680* | |
H44B | 0.86450 | 0.62270 | 1.05360 | 0.0680* | |
H45A | 0.88850 | 0.42130 | 1.21660 | 0.1530* | |
H45B | 0.85630 | 0.34580 | 1.14180 | 0.1530* | |
H45C | 0.73950 | 0.46320 | 1.17790 | 0.1530* | |
H46A | 0.83980 | 0.30730 | 0.83880 | 0.0590* | |
H46B | 0.83630 | 0.29260 | 0.97540 | 0.0590* | |
H48A | 0.42700 | 0.40200 | 0.76460 | 0.1500* | |
H48B | 0.41070 | 0.50760 | 0.82960 | 0.1500* | |
H48C | 0.41350 | 0.35080 | 0.90880 | 0.1500* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.039 (2) | 0.048 (2) | 0.059 (2) | −0.0208 (16) | 0.0019 (16) | −0.0121 (16) |
O2 | 0.072 (3) | 0.052 (2) | 0.0323 (17) | −0.0181 (18) | 0.0000 (16) | −0.0129 (15) |
O3 | 0.058 (2) | 0.0464 (19) | 0.0372 (16) | −0.0265 (17) | 0.0132 (15) | −0.0186 (14) |
O4 | 0.061 (3) | 0.061 (2) | 0.057 (2) | −0.0185 (19) | 0.0179 (18) | −0.0292 (18) |
O5 | 0.112 (4) | 0.084 (3) | 0.0301 (19) | −0.019 (3) | −0.014 (2) | 0.0005 (19) |
O6 | 0.046 (3) | 0.104 (3) | 0.066 (2) | −0.026 (2) | −0.008 (2) | 0.016 (2) |
O7 | 0.054 (3) | 0.090 (3) | 0.066 (2) | −0.018 (2) | −0.021 (2) | −0.002 (2) |
N1 | 0.038 (2) | 0.036 (2) | 0.0360 (19) | −0.0110 (17) | −0.0061 (16) | −0.0141 (16) |
C1 | 0.036 (3) | 0.036 (2) | 0.039 (2) | −0.017 (2) | 0.0011 (19) | −0.0079 (19) |
C2 | 0.028 (2) | 0.042 (3) | 0.032 (2) | −0.0113 (19) | 0.0041 (18) | −0.0146 (19) |
C3 | 0.038 (3) | 0.035 (2) | 0.030 (2) | −0.012 (2) | −0.0013 (18) | −0.0122 (18) |
C4 | 0.022 (2) | 0.031 (2) | 0.040 (2) | −0.0008 (17) | −0.0061 (18) | −0.0135 (18) |
C5 | 0.034 (2) | 0.037 (2) | 0.027 (2) | −0.0103 (19) | −0.0060 (18) | −0.0126 (18) |
C6 | 0.036 (3) | 0.032 (2) | 0.038 (2) | −0.012 (2) | −0.0031 (19) | −0.0072 (19) |
C7 | 0.040 (3) | 0.035 (2) | 0.061 (3) | −0.015 (2) | −0.004 (2) | −0.018 (2) |
C8 | 0.035 (3) | 0.039 (3) | 0.076 (3) | −0.013 (2) | 0.015 (2) | −0.028 (2) |
C9 | 0.043 (3) | 0.035 (2) | 0.038 (2) | −0.006 (2) | 0.009 (2) | −0.014 (2) |
C10 | 0.054 (3) | 0.056 (3) | 0.051 (3) | −0.024 (3) | 0.004 (2) | −0.031 (2) |
C11 | 0.037 (3) | 0.055 (3) | 0.049 (3) | −0.019 (2) | 0.009 (2) | −0.028 (2) |
C12 | 0.078 (4) | 0.078 (4) | 0.063 (3) | −0.011 (3) | 0.006 (3) | −0.048 (3) |
C13 | 0.029 (2) | 0.037 (2) | 0.031 (2) | −0.0076 (19) | −0.0051 (18) | −0.0118 (18) |
C14 | 0.054 (4) | 0.069 (4) | 0.042 (3) | 0.014 (3) | −0.005 (3) | −0.016 (3) |
C15 | 0.078 (5) | 0.075 (4) | 0.046 (3) | 0.018 (3) | −0.024 (3) | 0.000 (3) |
C16 | 0.080 (4) | 0.062 (4) | 0.031 (3) | −0.018 (3) | −0.013 (3) | −0.008 (2) |
C17 | 0.062 (4) | 0.047 (3) | 0.039 (2) | −0.023 (3) | 0.008 (2) | −0.018 (2) |
C18 | 0.040 (3) | 0.034 (2) | 0.046 (3) | −0.004 (2) | −0.005 (2) | −0.014 (2) |
C19 | 0.168 (8) | 0.079 (4) | 0.033 (3) | −0.055 (5) | 0.033 (4) | −0.024 (3) |
C20 | 0.045 (3) | 0.046 (3) | 0.055 (3) | −0.017 (2) | 0.001 (2) | −0.024 (2) |
C21 | 0.076 (6) | 0.243 (12) | 0.180 (8) | −0.021 (6) | −0.029 (6) | −0.167 (8) |
C22 | 0.043 (3) | 0.035 (3) | 0.050 (3) | −0.011 (2) | 0.000 (2) | −0.005 (2) |
C23 | 0.053 (3) | 0.033 (3) | 0.048 (3) | −0.003 (2) | −0.008 (3) | −0.006 (2) |
C24 | 0.061 (5) | 0.136 (7) | 0.122 (6) | −0.018 (5) | −0.035 (4) | −0.023 (5) |
O8 | 0.050 (2) | 0.0303 (17) | 0.071 (2) | −0.0060 (15) | 0.0021 (17) | −0.0193 (16) |
O9 | 0.096 (3) | 0.054 (2) | 0.0351 (17) | −0.017 (2) | 0.0126 (18) | −0.0247 (16) |
O10 | 0.034 (2) | 0.070 (2) | 0.0387 (17) | −0.0055 (17) | −0.0028 (15) | −0.0121 (16) |
O11 | 0.051 (2) | 0.074 (3) | 0.0385 (18) | −0.030 (2) | 0.0055 (16) | −0.0053 (17) |
O12 | 0.065 (3) | 0.068 (2) | 0.067 (2) | −0.0001 (19) | −0.0044 (19) | −0.0496 (19) |
O13 | 0.077 (3) | 0.097 (3) | 0.089 (3) | −0.043 (3) | 0.023 (2) | −0.058 (3) |
O14 | 0.069 (3) | 0.054 (2) | 0.065 (2) | −0.010 (2) | −0.012 (2) | −0.0180 (18) |
N2 | 0.054 (3) | 0.0270 (19) | 0.0343 (18) | −0.0133 (18) | −0.0011 (17) | −0.0118 (16) |
C25 | 0.048 (3) | 0.024 (2) | 0.037 (2) | −0.006 (2) | 0.005 (2) | −0.0136 (18) |
C26 | 0.057 (3) | 0.041 (3) | 0.034 (2) | −0.025 (2) | 0.005 (2) | −0.014 (2) |
C27 | 0.039 (3) | 0.032 (2) | 0.027 (2) | −0.0110 (19) | 0.0016 (18) | −0.0094 (17) |
C28 | 0.047 (3) | 0.028 (2) | 0.029 (2) | −0.014 (2) | 0.0008 (19) | −0.0088 (18) |
C29 | 0.036 (3) | 0.050 (3) | 0.032 (2) | −0.015 (2) | −0.003 (2) | −0.015 (2) |
C30 | 0.032 (3) | 0.046 (3) | 0.040 (2) | −0.007 (2) | −0.013 (2) | −0.009 (2) |
C31 | 0.026 (2) | 0.052 (3) | 0.056 (3) | −0.013 (2) | −0.004 (2) | −0.016 (2) |
C32 | 0.042 (3) | 0.052 (3) | 0.031 (2) | −0.015 (2) | −0.001 (2) | −0.012 (2) |
C33 | 0.045 (3) | 0.053 (3) | 0.027 (2) | −0.010 (2) | −0.012 (2) | −0.004 (2) |
C34 | 0.031 (3) | 0.055 (3) | 0.038 (2) | −0.013 (2) | −0.006 (2) | −0.014 (2) |
C35 | 0.038 (3) | 0.034 (2) | 0.029 (2) | −0.012 (2) | −0.0037 (19) | −0.0085 (18) |
C36 | 0.060 (4) | 0.136 (6) | 0.060 (4) | −0.050 (4) | 0.014 (3) | −0.009 (4) |
C37 | 0.035 (3) | 0.033 (2) | 0.028 (2) | −0.0094 (19) | −0.0010 (18) | −0.0092 (18) |
C38 | 0.046 (3) | 0.040 (3) | 0.031 (2) | −0.013 (2) | −0.003 (2) | −0.0100 (19) |
C39 | 0.044 (3) | 0.043 (3) | 0.046 (3) | −0.012 (2) | −0.003 (2) | −0.022 (2) |
C40 | 0.046 (3) | 0.050 (3) | 0.047 (3) | −0.002 (2) | −0.008 (2) | −0.032 (2) |
C41 | 0.055 (3) | 0.068 (4) | 0.039 (3) | −0.020 (3) | 0.006 (2) | −0.025 (3) |
C42 | 0.065 (4) | 0.040 (3) | 0.036 (2) | −0.019 (3) | 0.003 (2) | −0.009 (2) |
C43 | 0.047 (4) | 0.160 (7) | 0.105 (5) | −0.014 (4) | 0.008 (3) | −0.108 (5) |
C44 | 0.066 (4) | 0.053 (3) | 0.045 (3) | 0.001 (3) | −0.012 (3) | −0.018 (2) |
C45 | 0.152 (8) | 0.095 (5) | 0.058 (4) | −0.042 (5) | −0.027 (4) | −0.010 (4) |
C46 | 0.053 (3) | 0.039 (3) | 0.055 (3) | −0.016 (2) | 0.013 (2) | −0.025 (2) |
C47 | 0.074 (4) | 0.045 (3) | 0.046 (3) | −0.027 (3) | 0.009 (3) | −0.023 (2) |
C48 | 0.098 (6) | 0.083 (5) | 0.121 (6) | −0.004 (4) | −0.051 (5) | −0.029 (4) |
O1—C1 | 1.403 (6) | C18—H18 | 0.93 |
O2—C2 | 1.216 (6) | C19—H19A | 0.96 |
O3—C5 | 1.235 (5) | C19—H19B | 0.96 |
O4—C9 | 1.369 (6) | C19—H19C | 0.96 |
O4—C12 | 1.437 (9) | C20—H20B | 0.97 |
O5—C16 | 1.365 (6) | C20—H20A | 0.97 |
O5—C19 | 1.427 (9) | C21—H21C | 0.96 |
O6—C23 | 1.187 (7) | C21—H21A | 0.96 |
O7—C23 | 1.306 (7) | C21—H21B | 0.96 |
O7—C24 | 1.443 (10) | C22—H22A | 0.97 |
O1—H1 | 0.82 | C22—H22B | 0.97 |
O8—C25 | 1.385 (7) | C24—H24C | 0.96 |
O9—C26 | 1.219 (6) | C24—H24B | 0.96 |
O10—C29 | 1.233 (7) | C24—H24A | 0.96 |
O11—C36 | 1.408 (9) | C25—C46 | 1.533 (7) |
O11—C32 | 1.361 (6) | C25—C26 | 1.550 (6) |
O12—C40 | 1.368 (7) | C26—C27 | 1.440 (7) |
O12—C43 | 1.435 (8) | C27—C29 | 1.468 (6) |
O13—C47 | 1.194 (7) | C27—C28 | 1.407 (5) |
O14—C48 | 1.462 (11) | C28—C37 | 1.448 (6) |
O14—C47 | 1.317 (7) | C29—C35 | 1.495 (6) |
O8—H8A | 0.82 | C30—C35 | 1.378 (8) |
N1—C4 | 1.332 (6) | C30—C31 | 1.385 (7) |
N1—C1 | 1.467 (5) | C31—C32 | 1.374 (7) |
N1—C20 | 1.472 (6) | C32—C33 | 1.384 (8) |
N2—C25 | 1.484 (6) | C33—C34 | 1.377 (7) |
N2—C44 | 1.476 (6) | C34—C35 | 1.397 (6) |
N2—C28 | 1.354 (6) | C37—C38 | 1.391 (7) |
C1—C22 | 1.519 (7) | C37—C42 | 1.392 (6) |
C1—C2 | 1.537 (8) | C38—C39 | 1.373 (7) |
C2—C3 | 1.448 (6) | C39—C40 | 1.383 (7) |
C3—C4 | 1.403 (6) | C40—C41 | 1.374 (8) |
C3—C5 | 1.446 (6) | C41—C42 | 1.382 (8) |
C4—C13 | 1.480 (6) | C44—C45 | 1.450 (8) |
C5—C6 | 1.493 (6) | C46—C47 | 1.496 (8) |
C6—C7 | 1.390 (7) | C30—H30 | 0.93 |
C6—C11 | 1.380 (7) | C31—H31 | 0.93 |
C7—C8 | 1.380 (7) | C33—H33 | 0.93 |
C8—C9 | 1.372 (8) | C34—H34 | 0.93 |
C9—C10 | 1.382 (8) | C36—H36A | 0.96 |
C10—C11 | 1.376 (7) | C36—H36B | 0.96 |
C13—C18 | 1.370 (7) | C36—H36C | 0.96 |
C13—C14 | 1.381 (7) | C38—H38 | 0.93 |
C14—C15 | 1.372 (7) | C39—H39 | 0.93 |
C15—C16 | 1.393 (9) | C41—H41 | 0.93 |
C16—C17 | 1.366 (8) | C42—H42 | 0.93 |
C17—C18 | 1.391 (6) | C43—H43A | 0.96 |
C20—C21 | 1.456 (11) | C43—H43B | 0.96 |
C22—C23 | 1.508 (8) | C43—H43C | 0.96 |
C7—H7 | 0.93 | C44—H44A | 0.97 |
C8—H8 | 0.93 | C44—H44B | 0.97 |
C10—H10 | 0.93 | C45—H45A | 0.96 |
C11—H11 | 0.93 | C45—H45B | 0.96 |
C12—H12B | 0.96 | C45—H45C | 0.96 |
C12—H12C | 0.96 | C46—H46A | 0.97 |
C12—H12A | 0.96 | C46—H46B | 0.97 |
C14—H14 | 0.93 | C48—H48A | 0.96 |
C15—H15 | 0.93 | C48—H48B | 0.96 |
C17—H17 | 0.93 | C48—H48C | 0.96 |
O1···O2 | 2.972 (5) | C34···H43Biv | 3.0872 |
O1···O10i | 2.844 (5) | C36···H43Cii | 2.6944 |
O1···C21 | 3.294 (11) | C36···H31 | 2.5083 |
O2···C6 | 3.122 (6) | C36···H45Bix | 2.9933 |
O2···C7 | 3.000 (6) | C37···H44B | 2.5429 |
O2···O1 | 2.972 (5) | C38···H18 | 3.0289 |
O2···C43ii | 3.159 (8) | C39···H18 | 2.9679 |
O3···C26 | 3.418 (7) | C40···H21Cv | 3.0882 |
O3···O8 | 2.754 (5) | C40···H21Av | 3.0959 |
O3···C25 | 3.318 (6) | C41···H43C | 2.8094 |
O3···C13 | 3.040 (5) | C41···H21Cv | 2.9226 |
O3···C14 | 3.193 (6) | C41···H43B | 2.7200 |
O6···C4 | 3.123 (7) | C42···H44B | 2.7750 |
O6···N1 | 2.803 (6) | C43···H41 | 2.5386 |
O6···C20 | 3.350 (7) | C43···H33viii | 2.8618 |
O8···O9 | 2.930 (5) | C44···H8A | 2.8828 |
O8···C20iii | 3.355 (7) | C45···H46B | 3.0698 |
O8···O3 | 2.754 (5) | C46···H45B | 3.0455 |
O9···O8 | 2.930 (5) | C47···H39iii | 3.0922 |
O9···C19iv | 3.211 (7) | H1···O10i | 2.0369 |
O9···C30 | 3.255 (6) | H1···C29i | 2.9999 |
O9···C35 | 3.258 (6) | H1···C34i | 3.0430 |
O10···C37 | 3.200 (5) | H1···H21B | 2.5184 |
O10···C1v | 3.401 (7) | H1···H34i | 2.4935 |
O10···O1v | 2.844 (5) | H7···O2 | 2.7597 |
O10···C38 | 3.361 (6) | H7···C2 | 2.7615 |
O12···C47vi | 3.389 (7) | H7···C3 | 2.7087 |
O13···N2 | 3.012 (7) | H8A···O3 | 1.9456 |
O13···C28 | 3.329 (7) | H8A···C5 | 2.9833 |
O14···C26 | 3.306 (7) | H8A···C44 | 2.8828 |
O1···H21B | 2.7180 | H8A···H44A | 2.3481 |
O1···H12Cvi | 2.5426 | H10···H22Aiii | 2.5048 |
O2···H31 | 2.6380 | H10···C12 | 2.5256 |
O2···H22B | 2.7639 | H10···H12B | 2.1790 |
O2···H7 | 2.7597 | H10···O5iv | 2.9103 |
O2···H43Bii | 2.7723 | H10···H12C | 2.4735 |
O3···H11 | 2.6292 | H11···O9 | 2.7254 |
O3···H30 | 2.7619 | H11···O3 | 2.6292 |
O3···H8A | 1.9456 | H12A···O13ii | 2.7509 |
O4···H42ii | 2.8582 | H12A···H45Cii | 2.4511 |
O4···H24Avii | 2.5409 | H12B···C10 | 2.6824 |
O4···H45Cii | 2.6097 | H12B···C15iv | 3.0023 |
O5···H10viii | 2.9103 | H12B···H15iv | 2.2302 |
O6···H38 | 2.7684 | H12B···H10 | 2.1790 |
O6···H24C | 2.6171 | H12C···O1iii | 2.5426 |
O6···H46Avi | 2.7927 | H12C···C10 | 2.8360 |
O6···H24B | 2.5380 | H12C···H10 | 2.4735 |
O7···H19Aix | 2.8519 | H14···C3 | 3.0603 |
O8···H20Aiii | 2.6403 | H14···H48Bi | 2.2997 |
O8···H44A | 2.4489 | H15···H12Bviii | 2.2302 |
O9···H11 | 2.7254 | H15···C12viii | 3.0548 |
O9···H46A | 2.8358 | H17···H19B | 2.3168 |
O9···H19Aiv | 2.4763 | H17···C19 | 2.5187 |
O10···H34 | 2.6600 | H17···H19C | 2.3123 |
O10···H1v | 2.0369 | H18···C39 | 2.9679 |
O11···H45Bix | 2.5573 | H18···C38 | 3.0289 |
O11···H46Bix | 2.7836 | H18···C20 | 3.0266 |
O12···H48Cvi | 2.7584 | H18···H20B | 2.3004 |
O12···H33viii | 2.7053 | H19A···O9viii | 2.4763 |
O13···H12Ax | 2.7509 | H19A···O7xi | 2.8519 |
O13···H48B | 2.5989 | H19B···C17 | 2.7403 |
O13···H48C | 2.6247 | H19B···H17 | 2.3168 |
O14···H39iii | 2.6245 | H19C···C31viii | 2.9611 |
N1···O6 | 2.803 (6) | H19C···C17 | 2.7581 |
N2···O13 | 3.012 (7) | H19C···C32viii | 3.0448 |
C1···O10i | 3.401 (7) | H19C···H17 | 2.3123 |
C2···C7 | 3.169 (8) | H20A···O8vi | 2.6403 |
C4···C23 | 3.525 (7) | H20A···C22 | 2.7606 |
C4···O6 | 3.123 (7) | H20A···H22A | 2.2571 |
C5···C14 | 3.398 (6) | H20B···H18 | 2.3004 |
C6···O2 | 3.122 (6) | H20B···C13 | 2.7158 |
C7···O2 | 3.000 (6) | H20B···C18 | 2.5781 |
C7···C2 | 3.169 (8) | H20B···H36Aviii | 2.5036 |
C13···O3 | 3.040 (5) | H21A···H36Aviii | 2.5227 |
C13···C21 | 3.542 (12) | H21A···C40i | 3.0959 |
C14···C5 | 3.398 (6) | H21B···O1 | 2.7180 |
C14···O3 | 3.193 (6) | H21B···H1 | 2.5184 |
C16···C44 | 3.561 (9) | H21C···C40i | 3.0882 |
C18···C20 | 3.239 (7) | H21C···C13 | 3.0685 |
C18···C38 | 3.516 (8) | H21C···C41i | 2.9226 |
C19···O9viii | 3.211 (7) | H22A···H10vi | 2.5048 |
C20···C18 | 3.239 (7) | H22A···C20 | 2.9002 |
C20···O8vi | 3.355 (7) | H22A···H20A | 2.2571 |
C20···O6 | 3.350 (7) | H22B···O2 | 2.7639 |
C21···C41i | 3.571 (11) | H24A···C12xii | 2.9589 |
C21···C39i | 3.533 (11) | H24A···O4xii | 2.5409 |
C21···C13 | 3.542 (12) | H24B···O6 | 2.5380 |
C21···O1 | 3.294 (11) | H24C···O6 | 2.6171 |
C21···C40i | 3.394 (11) | H30···O3 | 2.7619 |
C23···C4 | 3.525 (7) | H30···C5 | 2.8450 |
C25···O3 | 3.318 (6) | H30···C26 | 2.8158 |
C26···C30 | 3.247 (7) | H30···C27 | 2.6143 |
C26···O14 | 3.306 (7) | H31···O2 | 2.6380 |
C26···O3 | 3.418 (7) | H31···C36 | 2.5083 |
C27···C47 | 3.439 (7) | H31···H36B | 2.2748 |
C28···C47 | 3.411 (7) | H31···H36C | 2.3196 |
C28···O13 | 3.329 (7) | H33···O12iv | 2.7053 |
C29···C38 | 3.290 (7) | H33···C43iv | 2.8618 |
C30···O9 | 3.255 (6) | H34···O10 | 2.6600 |
C30···C26 | 3.247 (7) | H34···H1v | 2.4935 |
C33···C43iv | 3.581 (9) | H34···H43Biv | 2.5212 |
C35···O9 | 3.258 (6) | H36A···C21iv | 3.0735 |
C37···O10 | 3.200 (5) | H36A···H20Biv | 2.5036 |
C38···O10 | 3.361 (6) | H36A···H21Aiv | 2.5227 |
C38···C29 | 3.290 (7) | H36B···C31 | 2.7117 |
C38···C18 | 3.516 (8) | H36B···H31 | 2.2748 |
C39···C21v | 3.533 (11) | H36B···H43Cii | 2.5751 |
C40···C21v | 3.394 (11) | H36C···C31 | 2.7418 |
C41···C21v | 3.571 (11) | H36C···H31 | 2.3196 |
C42···C44 | 3.263 (9) | H36C···H43Cii | 2.3946 |
C43···C33viii | 3.581 (9) | H38···O6 | 2.7684 |
C43···O2x | 3.159 (8) | H38···C27 | 2.9593 |
C44···C42 | 3.263 (9) | H38···C29 | 2.9551 |
C44···C16 | 3.561 (9) | H39···O14vi | 2.6245 |
C45···C46 | 3.589 (9) | H39···C47vi | 3.0922 |
C46···C45 | 3.589 (9) | H41···C43 | 2.5386 |
C47···C28 | 3.411 (7) | H41···H43B | 2.2523 |
C47···O12iii | 3.389 (7) | H41···H43C | 2.4155 |
C47···C27 | 3.439 (7) | H42···O4x | 2.8582 |
C2···H7 | 2.7615 | H42···H45C | 2.5215 |
C3···H7 | 2.7087 | H43B···O2x | 2.7723 |
C3···H14 | 3.0603 | H43B···C34viii | 3.0872 |
C5···H8A | 2.9833 | H43B···C41 | 2.7200 |
C5···H30 | 2.8450 | H43B···H34viii | 2.5212 |
C10···H12B | 2.6824 | H43B···H41 | 2.2523 |
C10···H12C | 2.8360 | H43C···C36x | 2.6944 |
C12···H45Cii | 2.9783 | H43C···C41 | 2.8094 |
C12···H24Avii | 2.9589 | H43C···H36Bx | 2.5751 |
C12···H15iv | 3.0548 | H43C···H36Cx | 2.3946 |
C12···H10 | 2.5256 | H43C···H41 | 2.4155 |
C13···H21C | 3.0685 | H44A···O8 | 2.4489 |
C13···H20B | 2.7158 | H44A···H8A | 2.3481 |
C14···H48Bi | 3.0412 | H44B···C16 | 2.9760 |
C15···H12Bviii | 3.0023 | H44B···C17 | 2.8228 |
C16···H44B | 2.9760 | H44B···C37 | 2.5429 |
C17···H19C | 2.7581 | H44B···C42 | 2.7750 |
C17···H19B | 2.7403 | H45B···O11xi | 2.5573 |
C17···H44B | 2.8228 | H45B···C36xi | 2.9933 |
C18···H20B | 2.5781 | H45B···C46 | 3.0455 |
C19···H17 | 2.5187 | H45B···H46B | 2.3456 |
C20···H22A | 2.9002 | H45C···O4x | 2.6097 |
C20···H18 | 3.0266 | H45C···C12x | 2.9783 |
C21···H36Aviii | 3.0735 | H45C···H12Ax | 2.4511 |
C22···H20A | 2.7606 | H45C···H42 | 2.5215 |
C26···H30 | 2.8158 | H46A···O6iii | 2.7927 |
C27···H30 | 2.6143 | H46A···O9 | 2.8358 |
C27···H38 | 2.9593 | H46B···O11xi | 2.7836 |
C29···H1v | 2.9999 | H46B···C45 | 3.0698 |
C29···H38 | 2.9551 | H46B···H45B | 2.3456 |
C31···H36C | 2.7418 | H48B···O13 | 2.5989 |
C31···H36B | 2.7117 | H48B···C14v | 3.0412 |
C31···H19Civ | 2.9611 | H48B···H14v | 2.2997 |
C32···H19Civ | 3.0448 | H48C···O12iii | 2.7584 |
C34···H1v | 3.0430 | H48C···O13 | 2.6247 |
C9—O4—C12 | 117.3 (5) | C1—C22—H22A | 108.68 |
C16—O5—C19 | 117.8 (5) | H24B—C24—H24C | 109.47 |
C23—O7—C24 | 116.4 (5) | O7—C24—H24B | 109.45 |
C1—O1—H1 | 109.47 | O7—C24—H24C | 109.50 |
C32—O11—C36 | 117.2 (4) | O7—C24—H24A | 109.52 |
C40—O12—C43 | 117.3 (5) | H24A—C24—H24C | 109.45 |
C47—O14—C48 | 116.0 (5) | H24A—C24—H24B | 109.44 |
C25—O8—H8A | 109.46 | O8—C25—N2 | 112.4 (4) |
C1—N1—C20 | 122.0 (4) | O8—C25—C26 | 112.3 (4) |
C4—N1—C20 | 127.9 (4) | N2—C25—C26 | 102.3 (4) |
C1—N1—C4 | 110.1 (4) | N2—C25—C46 | 112.1 (4) |
C25—N2—C44 | 121.3 (4) | O8—C25—C46 | 107.3 (4) |
C25—N2—C28 | 110.2 (3) | C26—C25—C46 | 110.5 (4) |
C28—N2—C44 | 125.0 (4) | O9—C26—C27 | 131.3 (4) |
O1—C1—C2 | 112.3 (4) | C25—C26—C27 | 106.9 (4) |
O1—C1—C22 | 106.7 (4) | O9—C26—C25 | 121.7 (5) |
N1—C1—C22 | 112.0 (4) | C26—C27—C29 | 126.7 (4) |
O1—C1—N1 | 110.7 (4) | C28—C27—C29 | 125.5 (4) |
C2—C1—C22 | 112.2 (4) | C26—C27—C28 | 107.7 (4) |
N1—C1—C2 | 103.0 (4) | N2—C28—C37 | 121.1 (3) |
C1—C2—C3 | 106.9 (4) | C27—C28—C37 | 126.4 (4) |
O2—C2—C3 | 132.0 (5) | N2—C28—C27 | 112.3 (4) |
O2—C2—C1 | 121.1 (4) | O10—C29—C35 | 120.1 (4) |
C4—C3—C5 | 127.2 (3) | C27—C29—C35 | 117.4 (4) |
C2—C3—C5 | 125.9 (3) | O10—C29—C27 | 122.4 (4) |
C2—C3—C4 | 106.5 (4) | C31—C30—C35 | 120.7 (4) |
N1—C4—C13 | 120.3 (4) | C30—C31—C32 | 119.6 (5) |
C3—C4—C13 | 126.1 (4) | O11—C32—C31 | 125.0 (5) |
N1—C4—C3 | 113.5 (4) | C31—C32—C33 | 120.1 (4) |
O3—C5—C6 | 119.7 (4) | O11—C32—C33 | 114.9 (4) |
O3—C5—C3 | 121.8 (4) | C32—C33—C34 | 120.5 (4) |
C3—C5—C6 | 118.5 (3) | C33—C34—C35 | 119.5 (5) |
C7—C6—C11 | 118.3 (4) | C29—C35—C34 | 120.3 (5) |
C5—C6—C11 | 120.0 (4) | C30—C35—C34 | 119.4 (4) |
C5—C6—C7 | 121.7 (4) | C29—C35—C30 | 120.2 (4) |
C6—C7—C8 | 120.8 (5) | C28—C37—C42 | 122.4 (4) |
C7—C8—C9 | 120.1 (5) | C38—C37—C42 | 117.5 (4) |
O4—C9—C10 | 124.3 (5) | C28—C37—C38 | 120.1 (4) |
O4—C9—C8 | 116.0 (5) | C37—C38—C39 | 121.2 (4) |
C8—C9—C10 | 119.7 (5) | C38—C39—C40 | 120.2 (5) |
C9—C10—C11 | 120.1 (5) | O12—C40—C41 | 125.3 (4) |
C6—C11—C10 | 121.0 (5) | C39—C40—C41 | 119.8 (5) |
C14—C13—C18 | 118.7 (4) | O12—C40—C39 | 114.9 (5) |
C4—C13—C14 | 119.6 (4) | C40—C41—C42 | 119.6 (5) |
C4—C13—C18 | 121.6 (4) | C37—C42—C41 | 121.6 (5) |
C13—C14—C15 | 120.4 (6) | N2—C44—C45 | 117.1 (6) |
C14—C15—C16 | 120.5 (6) | C25—C46—C47 | 113.6 (4) |
C15—C16—C17 | 119.5 (5) | O13—C47—C46 | 125.1 (5) |
O5—C16—C15 | 115.7 (6) | O14—C47—C46 | 111.0 (4) |
O5—C16—C17 | 124.7 (6) | O13—C47—O14 | 123.8 (6) |
C16—C17—C18 | 119.4 (5) | C31—C30—H30 | 119.62 |
C13—C18—C17 | 121.5 (5) | C35—C30—H30 | 119.67 |
N1—C20—C21 | 114.1 (6) | C30—C31—H31 | 120.20 |
C1—C22—C23 | 114.5 (4) | C32—C31—H31 | 120.16 |
O6—C23—O7 | 122.8 (6) | C32—C33—H33 | 119.72 |
O7—C23—C22 | 112.2 (5) | C34—C33—H33 | 119.75 |
O6—C23—C22 | 124.8 (5) | C33—C34—H34 | 120.27 |
C8—C7—H7 | 119.59 | C35—C34—H34 | 120.20 |
C6—C7—H7 | 119.61 | O11—C36—H36A | 109.48 |
C9—C8—H8 | 120.03 | O11—C36—H36B | 109.44 |
C7—C8—H8 | 119.90 | O11—C36—H36C | 109.50 |
C11—C10—H10 | 119.97 | H36A—C36—H36B | 109.46 |
C9—C10—H10 | 119.97 | H36A—C36—H36C | 109.46 |
C6—C11—H11 | 119.42 | H36B—C36—H36C | 109.50 |
C10—C11—H11 | 119.55 | C37—C38—H38 | 119.44 |
H12A—C12—H12B | 109.46 | C39—C38—H38 | 119.36 |
O4—C12—H12C | 109.51 | C38—C39—H39 | 119.82 |
O4—C12—H12B | 109.50 | C40—C39—H39 | 119.94 |
O4—C12—H12A | 109.37 | C40—C41—H41 | 120.15 |
H12B—C12—H12C | 109.52 | C42—C41—H41 | 120.21 |
H12A—C12—H12C | 109.47 | C37—C42—H42 | 119.24 |
C13—C14—H14 | 119.80 | C41—C42—H42 | 119.21 |
C15—C14—H14 | 119.77 | O12—C43—H43A | 109.49 |
C16—C15—H15 | 119.80 | O12—C43—H43B | 109.46 |
C14—C15—H15 | 119.75 | O12—C43—H43C | 109.44 |
C16—C17—H17 | 120.36 | H43A—C43—H43B | 109.52 |
C18—C17—H17 | 120.28 | H43A—C43—H43C | 109.49 |
C17—C18—H18 | 119.24 | H43B—C43—H43C | 109.43 |
C13—C18—H18 | 119.23 | N2—C44—H44A | 108.02 |
H19A—C19—H19C | 109.43 | N2—C44—H44B | 108.02 |
H19B—C19—H19C | 109.48 | C45—C44—H44A | 108.05 |
H19A—C19—H19B | 109.47 | C45—C44—H44B | 108.03 |
O5—C19—H19B | 109.50 | H44A—C44—H44B | 107.25 |
O5—C19—H19C | 109.48 | C44—C45—H45A | 109.45 |
O5—C19—H19A | 109.47 | C44—C45—H45B | 109.47 |
N1—C20—H20A | 108.80 | C44—C45—H45C | 109.45 |
N1—C20—H20B | 108.76 | H45A—C45—H45B | 109.49 |
C21—C20—H20B | 108.73 | H45A—C45—H45C | 109.48 |
H20A—C20—H20B | 107.62 | H45B—C45—H45C | 109.49 |
C21—C20—H20A | 108.69 | C25—C46—H46A | 108.80 |
C20—C21—H21B | 109.44 | C25—C46—H46B | 108.78 |
C20—C21—H21A | 109.49 | C47—C46—H46A | 108.89 |
H21A—C21—H21C | 109.51 | C47—C46—H46B | 108.83 |
C20—C21—H21C | 109.41 | H46A—C46—H46B | 107.75 |
H21A—C21—H21B | 109.53 | O14—C48—H48A | 109.48 |
H21B—C21—H21C | 109.44 | O14—C48—H48B | 109.49 |
C23—C22—H22B | 108.58 | O14—C48—H48C | 109.44 |
C23—C22—H22A | 108.68 | H48A—C48—H48B | 109.47 |
C1—C22—H22B | 108.62 | H48A—C48—H48C | 109.48 |
H22A—C22—H22B | 107.62 | H48B—C48—H48C | 109.47 |
C12—O4—C9—C8 | 167.1 (5) | C6—C7—C8—C9 | 1.6 (8) |
C12—O4—C9—C10 | −12.9 (7) | C7—C8—C9—C10 | −1.4 (8) |
C19—O5—C16—C15 | −177.4 (6) | C7—C8—C9—O4 | 178.6 (5) |
C19—O5—C16—C17 | −0.5 (10) | C8—C9—C10—C11 | 1.5 (8) |
C24—O7—C23—O6 | 0.3 (9) | O4—C9—C10—C11 | −178.6 (5) |
C24—O7—C23—C22 | −176.5 (6) | C9—C10—C11—C6 | −1.6 (7) |
C36—O11—C32—C33 | 177.6 (5) | C18—C13—C14—C15 | 0.9 (8) |
C36—O11—C32—C31 | −2.1 (8) | C14—C13—C18—C17 | 0.0 (8) |
C43—O12—C40—C41 | −7.5 (8) | C4—C13—C18—C17 | 177.6 (5) |
C43—O12—C40—C39 | 172.1 (5) | C4—C13—C14—C15 | −176.7 (5) |
C48—O14—C47—O13 | −2.9 (8) | C13—C14—C15—C16 | −1.4 (10) |
C48—O14—C47—C46 | 178.5 (5) | C14—C15—C16—O5 | 178.0 (6) |
C4—N1—C1—O1 | −121.1 (4) | C14—C15—C16—C17 | 0.9 (11) |
C20—N1—C4—C3 | −175.3 (5) | C15—C16—C17—C18 | 0.0 (10) |
C20—N1—C1—C2 | 176.4 (4) | O5—C16—C17—C18 | −176.8 (6) |
C4—N1—C1—C22 | 120.0 (5) | C16—C17—C18—C13 | −0.5 (9) |
C1—N1—C4—C3 | 1.7 (6) | C1—C22—C23—O6 | 43.7 (8) |
C20—N1—C1—O1 | 56.1 (6) | C1—C22—C23—O7 | −139.6 (5) |
C20—N1—C1—C22 | −62.8 (6) | C46—C25—C26—O9 | −64.5 (6) |
C1—N1—C4—C13 | −178.4 (4) | C46—C25—C26—C27 | 111.9 (4) |
C4—N1—C1—C2 | −0.8 (5) | O8—C25—C46—C47 | 178.7 (4) |
C20—N1—C4—C13 | 4.6 (7) | N2—C25—C26—C27 | −7.6 (5) |
C1—N1—C20—C21 | −94.2 (7) | O8—C25—C26—C27 | −128.3 (4) |
C4—N1—C20—C21 | 82.5 (7) | N2—C25—C26—O9 | 176.1 (5) |
C44—N2—C28—C27 | 156.0 (4) | O8—C25—C26—O9 | 55.4 (7) |
C28—N2—C25—C46 | −111.9 (4) | C26—C25—C46—C47 | −58.5 (5) |
C44—N2—C25—C46 | 88.2 (5) | N2—C25—C46—C47 | 54.9 (5) |
C44—N2—C25—O8 | −32.7 (6) | C25—C26—C27—C28 | 6.2 (5) |
C25—N2—C28—C27 | −3.1 (6) | O9—C26—C27—C29 | 0.4 (9) |
C28—N2—C25—O8 | 127.2 (4) | C25—C26—C27—C29 | −175.5 (5) |
C44—N2—C25—C26 | −153.4 (4) | O9—C26—C27—C28 | −177.9 (6) |
C28—N2—C44—C45 | 117.6 (6) | C29—C27—C28—C37 | −6.5 (8) |
C28—N2—C25—C26 | 6.5 (5) | C28—C27—C29—C35 | 131.5 (5) |
C25—N2—C28—C37 | −177.5 (4) | C26—C27—C28—C37 | 171.9 (5) |
C44—N2—C28—C37 | −18.5 (7) | C26—C27—C28—N2 | −2.2 (6) |
C25—N2—C44—C45 | −85.5 (7) | C28—C27—C29—O10 | −45.8 (8) |
N1—C1—C2—O2 | 177.5 (5) | C26—C27—C29—C35 | −46.5 (7) |
N1—C1—C22—C23 | −54.6 (6) | C26—C27—C29—O10 | 136.2 (5) |
O1—C1—C22—C23 | −175.9 (4) | C29—C27—C28—N2 | 179.5 (4) |
C22—C1—C2—O2 | 56.9 (6) | C27—C28—C37—C42 | 130.5 (5) |
C2—C1—C22—C23 | 60.7 (5) | N2—C28—C37—C42 | −55.9 (7) |
C22—C1—C2—C3 | −120.9 (4) | C27—C28—C37—C38 | −52.9 (7) |
O1—C1—C2—C3 | 118.9 (4) | N2—C28—C37—C38 | 120.7 (5) |
O1—C1—C2—O2 | −63.3 (6) | C27—C29—C35—C30 | −30.0 (7) |
N1—C1—C2—C3 | −0.3 (5) | O10—C29—C35—C34 | −29.2 (7) |
C1—C2—C3—C5 | 173.6 (4) | C27—C29—C35—C34 | 153.4 (5) |
O2—C2—C3—C5 | −3.9 (8) | O10—C29—C35—C30 | 147.4 (5) |
O2—C2—C3—C4 | −176.3 (5) | C31—C30—C35—C29 | −174.3 (5) |
C1—C2—C3—C4 | 1.2 (5) | C35—C30—C31—C32 | −3.0 (8) |
C2—C3—C5—C6 | 35.6 (6) | C31—C30—C35—C34 | 2.4 (7) |
C4—C3—C5—O3 | 26.0 (7) | C30—C31—C32—O11 | −178.7 (5) |
C4—C3—C5—C6 | −153.5 (4) | C30—C31—C32—C33 | 1.6 (8) |
C5—C3—C4—C13 | 5.9 (7) | O11—C32—C33—C34 | −179.3 (5) |
C5—C3—C4—N1 | −174.1 (4) | C31—C32—C33—C34 | 0.4 (8) |
C2—C3—C4—N1 | −1.8 (5) | C32—C33—C34—C35 | −1.0 (8) |
C2—C3—C4—C13 | 178.2 (4) | C33—C34—C35—C30 | −0.4 (7) |
C2—C3—C5—O3 | −144.8 (4) | C33—C34—C35—C29 | 176.3 (5) |
C3—C4—C13—C14 | 58.8 (7) | C42—C37—C38—C39 | 0.8 (7) |
N1—C4—C13—C14 | −121.2 (5) | C38—C37—C42—C41 | 1.5 (8) |
N1—C4—C13—C18 | 61.3 (6) | C28—C37—C42—C41 | 178.1 (5) |
C3—C4—C13—C18 | −118.7 (5) | C28—C37—C38—C39 | −175.9 (5) |
O3—C5—C6—C7 | −147.2 (4) | C37—C38—C39—C40 | −1.6 (8) |
O3—C5—C6—C11 | 30.9 (6) | C38—C39—C40—O12 | −179.7 (5) |
C3—C5—C6—C7 | 32.3 (6) | C38—C39—C40—C41 | 0.0 (8) |
C3—C5—C6—C11 | −149.6 (4) | O12—C40—C41—C42 | −178.1 (5) |
C7—C6—C11—C10 | 1.7 (7) | C39—C40—C41—C42 | 2.2 (8) |
C5—C6—C7—C8 | 176.4 (4) | C40—C41—C42—C37 | −3.0 (9) |
C5—C6—C11—C10 | −176.4 (4) | C25—C46—C47—O13 | −72.5 (6) |
C11—C6—C7—C8 | −1.7 (7) | C25—C46—C47—O14 | 106.1 (5) |
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z−1; (iii) x, y−1, z; (iv) x, y, z−1; (v) x−1, y, z; (vi) x, y+1, z; (vii) x+1, y−1, z; (viii) x, y, z+1; (ix) x, y+1, z−1; (x) x−1, y, z+1; (xi) x, y−1, z+1; (xii) x−1, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O10i | 0.82 | 2.04 | 2.844 (5) | 168 |
O8—H8A···O3 | 0.82 | 1.95 | 2.754 (5) | 169 |
C12—H12C···O1iii | 0.96 | 2.54 | 3.434 (7) | 155 |
C19—H19A···O9viii | 0.96 | 2.48 | 3.211 (7) | 133 |
C24—H24A···O4xii | 0.96 | 2.54 | 3.440 (10) | 156 |
C44—H44A···O8 | 0.97 | 2.45 | 2.869 (6) | 106 |
C45—H45B···O11xi | 0.96 | 2.56 | 3.471 (10) | 159 |
Symmetry codes: (i) x+1, y, z; (iii) x, y−1, z; (viii) x, y, z+1; (xi) x, y−1, z+1; (xii) x−1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C24H25NO7 |
Mr | 439.45 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 10.160 (5), 10.785 (5), 11.942 (5) |
α, β, γ (°) | 66.369 (5), 75.928 (5), 72.005 (5) |
V (Å3) | 1129.4 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.52 × 0.26 × 0.20 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Part of the refinement model (ΔF) [Parkin et al., 1995; cubic fit to sin(θ)/λ with 24 parameters] |
Tmin, Tmax | 0.952, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6035, 6035, 4369 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.127, 1.11 |
No. of reflections | 6035 |
No. of parameters | 577 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.19 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SIR97 (Altomare, 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), PARST (Nardelli, 1995) and WinGX (Farrugia, 1999).
O1—C1 | 1.403 (6) | O11—C36 | 1.408 (9) |
O2—C2 | 1.216 (6) | O11—C32 | 1.361 (6) |
O3—C5 | 1.235 (5) | O12—C40 | 1.368 (7) |
O4—C9 | 1.369 (6) | O12—C43 | 1.435 (8) |
O4—C12 | 1.437 (9) | O13—C47 | 1.194 (7) |
O5—C16 | 1.365 (6) | O14—C48 | 1.462 (11) |
O5—C19 | 1.427 (9) | O14—C47 | 1.317 (7) |
O6—C23 | 1.187 (7) | N1—C4 | 1.332 (6) |
O7—C23 | 1.306 (7) | N1—C1 | 1.467 (5) |
O7—C24 | 1.443 (10) | N1—C20 | 1.472 (6) |
O8—C25 | 1.385 (7) | N2—C25 | 1.484 (6) |
O9—C26 | 1.219 (6) | N2—C44 | 1.476 (6) |
O10—C29 | 1.233 (7) | N2—C28 | 1.354 (6) |
C9—O4—C12 | 117.3 (5) | O5—C16—C15 | 115.7 (6) |
C16—O5—C19 | 117.8 (5) | O5—C16—C17 | 124.7 (6) |
C23—O7—C24 | 116.4 (5) | N1—C20—C21 | 114.1 (6) |
C32—O11—C36 | 117.2 (4) | O6—C23—O7 | 122.8 (6) |
C40—O12—C43 | 117.3 (5) | O7—C23—C22 | 112.2 (5) |
C47—O14—C48 | 116.0 (5) | O6—C23—C22 | 124.8 (5) |
C1—N1—C20 | 122.0 (4) | O8—C25—N2 | 112.4 (4) |
C4—N1—C20 | 127.9 (4) | O8—C25—C26 | 112.3 (4) |
C1—N1—C4 | 110.1 (4) | N2—C25—C26 | 102.3 (4) |
C25—N2—C44 | 121.3 (4) | N2—C25—C46 | 112.1 (4) |
C25—N2—C28 | 110.2 (3) | O8—C25—C46 | 107.3 (4) |
C28—N2—C44 | 125.0 (4) | O9—C26—C27 | 131.3 (4) |
O1—C1—C2 | 112.3 (4) | O9—C26—C25 | 121.7 (5) |
O1—C1—C22 | 106.7 (4) | N2—C28—C37 | 121.1 (3) |
N1—C1—C22 | 112.0 (4) | N2—C28—C27 | 112.3 (4) |
O1—C1—N1 | 110.7 (4) | O10—C29—C35 | 120.1 (4) |
N1—C1—C2 | 103.0 (4) | O10—C29—C27 | 122.4 (4) |
O2—C2—C3 | 132.0 (5) | O11—C32—C31 | 125.0 (5) |
O2—C2—C1 | 121.1 (4) | O11—C32—C33 | 114.9 (4) |
N1—C4—C13 | 120.3 (4) | O12—C40—C41 | 125.3 (4) |
N1—C4—C3 | 113.5 (4) | O12—C40—C39 | 114.9 (5) |
O3—C5—C6 | 119.7 (4) | N2—C44—C45 | 117.1 (6) |
O3—C5—C3 | 121.8 (4) | O13—C47—C46 | 125.1 (5) |
O4—C9—C10 | 124.3 (5) | O14—C47—C46 | 111.0 (4) |
O4—C9—C8 | 116.0 (5) | O13—C47—O14 | 123.8 (6) |
C24—O7—C23—O6 | 0.3 (9) | O1—C1—C2—C3 | 118.9 (4) |
C24—O7—C23—C22 | −176.5 (6) | O1—C1—C2—O2 | −63.3 (6) |
C48—O14—C47—O13 | −2.9 (8) | O2—C2—C3—C4 | −176.3 (5) |
C48—O14—C47—C46 | 178.5 (5) | C1—C22—C23—O6 | 43.7 (8) |
C4—N1—C1—O1 | −121.1 (4) | O8—C25—C26—C27 | −128.3 (4) |
C1—N1—C20—C21 | −94.2 (7) | N2—C25—C26—O9 | 176.1 (5) |
C4—N1—C20—C21 | 82.5 (7) | O8—C25—C26—O9 | 55.4 (7) |
C28—N2—C25—O8 | 127.2 (4) | C26—C25—C46—C47 | −58.5 (5) |
C28—N2—C44—C45 | 117.6 (6) | N2—C25—C46—C47 | 54.9 (5) |
C25—N2—C44—C45 | −85.5 (7) | O9—C26—C27—C28 | −177.9 (6) |
N1—C1—C2—O2 | 177.5 (5) | C25—C46—C47—O13 | −72.5 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O10i | 0.82 | 2.04 | 2.844 (5) | 168 |
O8—H8A···O3 | 0.82 | 1.95 | 2.754 (5) | 169 |
C12—H12C···O1ii | 0.96 | 2.54 | 3.434 (7) | 155 |
C19—H19A···O9iii | 0.96 | 2.48 | 3.211 (7) | 133 |
C24—H24A···O4iv | 0.96 | 2.54 | 3.440 (10) | 156 |
C44—H44A···O8 | 0.97 | 2.45 | 2.869 (6) | 106 |
C45—H45B···O11v | 0.96 | 2.56 | 3.471 (10) | 159 |
Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z; (iii) x, y, z+1; (iv) x−1, y+1, z; (v) x, y−1, z+1. |
Pyrrolones have received considerable attention, as a result of the presence of the lactam ring in some antibiotics, in bile pigments and in the natural alkaloid jatropham, which shows inhibitory activity towards P-338 lymphocytic leukaemia (Jimenez et al., 1988; Gossauer, 1983; Wiedhopf et al., 1973). Among these chemical structures, 2,3-dihydro-1H-3-pyrrolone derivatives (Weigele et al., 1972, 1976; Gelin & Gelin, 1979; Chantegrel & Gelin, 1978; Koz'minykh & Andrechikov, 1988) exhibit remarkable antimicrobiological and pharmacological activities (Koz'minykh et al., 1992, 1996, 2002). In the light of this, we have synthesized the title compound, (I), which consists of two enantiomers, and present its X-ray crystal structure here. \sch
The two molecules in the asymmetric unit of (I), (Ia) and (Ib), are enantiomorphs of each other, as shown in Figs. 1 and 2 and via the torsion angles in Table 1. The bond lengths are almost identical in both molecules and are comparable with those in related structures (Allen et al., 1987). In molecule (Ia), the angles between planes A (N1/C1—C4), B (C6—C11) and C (C13—C18) are A/B 57.4 (2), A/C 60.0 (2) and B/C 85.5 (2)°. In molecule (Ib), the equivalent planes are D (N2/C25—C28), E (C30—C35) and F (C37—C42), and the angles between them are D/E 69.4 (2), D/F 54.7 (2) and E/F 89.0 (2)°. These values are similar to those in 2(R)-hydroxy-4-(4-methoxybenzoyl)-2-methoxycarbonylmethyl-5-(4-methoxy- phenyl)-1-(2-methylphenyl)-2,3-dihydro-1H-3-pyrrolone (Öztürk et al., 2003). The angles between the planes of similar rings of the two enantiomorphic molecules of (I) are not identical, with values of A/D 41.6 (2), B/E 68.2 (2) and C/F 51.1 (2)°.
We have carried out CNDO Please define calculations on (I), and the calculated charge distribution on the molecule of (I) in the gas phase is shown in Fig. 3. The dipole moment of (I) is σim 5.25 D. The highest occupied and lowest unoccupied molecular orbital energy levels are −10.1370 and 1.1187 eV, respectively.
The crystal structure of (I) reveals a number of three-dimensional O—H···O and C—H···O short hydrogen contacts. Details of these contacts are given in Table 2.