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The title compound, C24H25NO7, is a racemic mixture of 2,3-di­hydro-1H-pyrrol-3-ones. It crystallizes in the triclinic system, space group P1, with Z = 2. The asymmetric unit contains two enantiomorphic mol­ecules and the structure is stabilized by hydrogen-bond contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103018584/ty1001sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103018584/ty1001Isup2.hkl
Contains datablock I

CCDC reference: 224673

Comment top

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.

Experimental top

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 (C12O), 1678.69 (C8O), 1674.39 (C4O), 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, CH2CO), 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 (CC, arom. and aliph.), 182.945 (C12O), 188.924 (C8O), 196.037 (C4O). Analysis calculated for C24H25NO7: C 65.59, N 3.19, H 5.73%; found: C 65.41, N 3.30, H 5.72%.

Refinement top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of molecule (Ia), showing the atom-numbering scheme and with displacement ellipsoids drawn at the 20% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The molecular structure of molecule (Ib), showing the atom-numbering scheme and with displacement ellipsoids drawn at the 20% probability level. H atoms have been omitted for clarity.
[Figure 3] Fig. 3. The CNDO-calculated charge distribution for (I).
Methyl (±)-1-ethyl-2-hydroxy-4-(4-methoxybenzoyl)-5-(4-methoxyphenyl)-3-oxo- 2,3-dihydro-1H-pyrrole-2-acetate top
Crystal data top
C24H25NO7Z = 2
Mr = 439.45F(000) = 464
Triclinic, P1Dx = 1.292 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.160 (5) ÅCell parameters from 2644 reflections
b = 10.785 (5) Åθ = 4.6–49.1°
c = 11.942 (5) ŵ = 0.10 mm1
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
Data collection top
Siemens SMART CCD area-detector
diffractometer
6035 independent reflections
Radiation source: fine-focus sealed tube4369 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.3°
ω scansh = 1313
Absorption correction: part of the refinement model (ΔF)
[Parkin et al., 1995; cubic fit to sin(θ)/λ with 24 parameters]
k = 1411
Tmin = 0.952, Tmax = 0.981l = 1515
6035 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-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 parametersΔρmax = 0.22 e Å3
3 restraintsΔρmin = 0.19 e Å3
Crystal data top
C24H25NO7γ = 72.005 (5)°
Mr = 439.45V = 1129.4 (9) Å3
Triclinic, P1Z = 2
a = 10.160 (5) ÅMo Kα radiation
b = 10.785 (5) ŵ = 0.10 mm1
c = 11.942 (5) ÅT = 293 K
α = 66.369 (5)°0.52 × 0.26 × 0.20 mm
β = 75.928 (5)°
Data collection top
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 = 0.981Rint = 0.000
6035 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0663 restraints
wR(F2) = 0.127H-atom parameters constrained
S = 1.11Δρmax = 0.22 e Å3
6035 reflectionsΔρmin = 0.19 e Å3
577 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.3476 (3)1.1448 (3)0.5652 (3)0.0500 (12)
O21.2440 (4)0.9979 (3)0.4530 (3)0.0533 (13)
O31.1016 (3)0.6744 (3)0.7612 (2)0.0462 (11)
O41.5072 (4)0.5016 (4)0.3256 (3)0.0608 (14)
O51.0551 (5)0.5846 (4)1.2672 (3)0.0824 (18)
O60.9148 (4)1.1505 (5)0.6855 (3)0.0852 (16)
O70.8889 (4)1.2756 (4)0.4922 (3)0.0758 (16)
N11.1913 (4)1.0449 (4)0.7364 (3)0.0355 (11)
C11.2207 (5)1.1041 (5)0.6015 (4)0.0379 (14)
C21.2259 (4)0.9836 (5)0.5615 (4)0.0343 (14)
C31.2006 (4)0.8679 (4)0.6731 (3)0.0339 (14)
C41.1789 (4)0.9147 (4)0.7716 (4)0.0317 (12)
C51.1827 (4)0.7375 (4)0.6789 (3)0.0314 (12)
C61.2661 (5)0.6782 (4)0.5826 (4)0.0365 (14)
C71.3995 (5)0.6974 (5)0.5294 (4)0.0440 (16)
C81.4779 (5)0.6354 (5)0.4455 (5)0.0507 (17)
C91.4232 (5)0.5564 (5)0.4113 (4)0.0419 (14)
C101.2906 (6)0.5367 (5)0.4633 (4)0.0491 (17)
C111.2127 (5)0.5987 (5)0.5469 (4)0.0447 (17)
C121.4666 (7)0.3955 (7)0.3072 (5)0.070 (2)
C131.1453 (4)0.8337 (4)0.9039 (3)0.0323 (12)
C141.2361 (6)0.7093 (6)0.9591 (4)0.064 (2)
C151.2034 (7)0.6294 (7)1.0799 (5)0.079 (2)
C161.0796 (7)0.6740 (6)1.1493 (4)0.059 (2)
C170.9896 (6)0.7974 (5)1.0957 (4)0.0488 (18)
C181.0233 (5)0.8763 (5)0.9726 (4)0.0414 (16)
C190.9268 (9)0.6230 (7)1.3403 (5)0.095 (3)
C201.1851 (5)1.1227 (5)0.8153 (4)0.0466 (17)
C211.3161 (8)1.0936 (11)0.8606 (9)0.138 (5)
C221.1088 (5)1.2331 (5)0.5471 (4)0.0468 (17)
C230.9622 (6)1.2120 (5)0.5840 (5)0.0490 (17)
C240.7445 (8)1.2684 (10)0.5202 (7)0.111 (3)
O81.0135 (4)0.4316 (3)0.8427 (3)0.0528 (11)
O90.8557 (4)0.5556 (3)0.6328 (3)0.0630 (13)
O100.5337 (3)0.8905 (4)0.6839 (3)0.0520 (11)
O110.9333 (4)1.0830 (4)0.1876 (3)0.0578 (13)
O120.5278 (4)1.1040 (4)1.0837 (3)0.0629 (14)
O130.5754 (5)0.4318 (5)0.9933 (4)0.0804 (17)
O140.6022 (4)0.3825 (4)0.8247 (3)0.0643 (14)
N20.8153 (4)0.5672 (3)0.9307 (3)0.0381 (13)
C250.8699 (5)0.4819 (4)0.8506 (4)0.0381 (14)
C260.8229 (5)0.5864 (5)0.7252 (4)0.0426 (16)
C270.7334 (4)0.7095 (4)0.7471 (3)0.0335 (14)
C280.7359 (5)0.6926 (4)0.8697 (3)0.0350 (14)
C290.6561 (5)0.8330 (5)0.6576 (4)0.0383 (16)
C300.8752 (5)0.8798 (5)0.5179 (4)0.0404 (16)
C310.9458 (5)0.9448 (5)0.4044 (4)0.0451 (16)
C320.8750 (5)1.0172 (5)0.3039 (4)0.0424 (16)
C330.7332 (5)1.0279 (5)0.3169 (4)0.0441 (16)
C340.6616 (5)0.9671 (5)0.4303 (4)0.0412 (16)
C350.7335 (5)0.8923 (4)0.5324 (3)0.0339 (14)
C361.0762 (7)1.0799 (8)0.1703 (5)0.091 (3)
C370.6748 (4)0.7976 (4)0.9262 (3)0.0328 (14)
C380.7073 (5)0.9271 (5)0.8708 (4)0.0396 (16)
C390.6577 (5)1.0253 (5)0.9263 (4)0.0424 (17)
C400.5710 (5)0.9981 (5)1.0379 (4)0.0447 (17)
C410.5345 (6)0.8723 (6)1.0933 (4)0.0530 (19)
C420.5887 (6)0.7721 (5)1.0391 (4)0.0487 (18)
C430.4237 (6)1.0892 (8)1.1906 (6)0.090 (3)
C440.8817 (6)0.5364 (6)1.0390 (4)0.0573 (19)
C450.8378 (10)0.4329 (8)1.1535 (5)0.102 (3)
C460.8054 (5)0.3560 (5)0.8969 (4)0.0488 (17)
C470.6491 (6)0.3937 (5)0.9130 (4)0.0528 (19)
C480.4503 (9)0.4134 (8)0.8326 (7)0.100 (3)
H11.410801.077400.593100.0750*
H71.436400.752700.550600.0530*
H81.567900.647300.412100.0610*
H101.254000.481500.441800.0600*
H111.122600.586900.579900.0530*
H12A1.533000.366100.244900.1060*
H12B1.375700.432200.281200.1060*
H12C1.464200.317400.383000.1060*
H141.320000.679400.914000.0760*
H151.264400.544901.115700.0950*
H170.906700.828401.141000.0580*
H180.961600.959900.936100.0500*
H19A0.922200.551401.420400.1420*
H19B0.849900.634301.300900.1420*
H19C0.922000.709101.348900.1420*
H20A1.157801.221700.768900.0560*
H20B1.113301.100400.885400.0560*
H21A1.304701.148400.910300.2070*
H21B1.387701.116600.791900.2070*
H21C1.342300.996400.909400.2070*
H22A1.112801.306600.572400.0560*
H22B1.129701.264200.457800.0560*
H24A0.699101.323000.448000.1670*
H24B0.698701.304200.585200.1670*
H24C0.739501.173200.546100.1670*
H8A1.050900.496900.818600.0790*
H300.924000.827200.585000.0480*
H311.040600.939400.396200.0540*
H330.685901.076600.248500.0530*
H340.566100.975800.438900.0490*
H36A1.105201.129000.085100.1370*
H36B1.129500.984900.193500.1370*
H36C1.091401.123600.220500.1370*
H380.763600.947600.794800.0470*
H390.682401.110400.888600.0510*
H410.473700.854701.166900.0640*
H420.567000.685601.079000.0590*
H43A0.402501.169401.213900.1340*
H43B0.458301.007101.257300.1340*
H43C0.340501.081101.172000.1340*
H44A0.981800.505901.018200.0680*
H44B0.864500.622701.053600.0680*
H45A0.888500.421301.216600.1530*
H45B0.856300.345801.141800.1530*
H45C0.739500.463201.177900.1530*
H46A0.839800.307300.838800.0590*
H46B0.836300.292600.975400.0590*
H48A0.427000.402000.764600.1500*
H48B0.410700.507600.829600.1500*
H48C0.413500.350800.908800.1500*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.039 (2)0.048 (2)0.059 (2)0.0208 (16)0.0019 (16)0.0121 (16)
O20.072 (3)0.052 (2)0.0323 (17)0.0181 (18)0.0000 (16)0.0129 (15)
O30.058 (2)0.0464 (19)0.0372 (16)0.0265 (17)0.0132 (15)0.0186 (14)
O40.061 (3)0.061 (2)0.057 (2)0.0185 (19)0.0179 (18)0.0292 (18)
O50.112 (4)0.084 (3)0.0301 (19)0.019 (3)0.014 (2)0.0005 (19)
O60.046 (3)0.104 (3)0.066 (2)0.026 (2)0.008 (2)0.016 (2)
O70.054 (3)0.090 (3)0.066 (2)0.018 (2)0.021 (2)0.002 (2)
N10.038 (2)0.036 (2)0.0360 (19)0.0110 (17)0.0061 (16)0.0141 (16)
C10.036 (3)0.036 (2)0.039 (2)0.017 (2)0.0011 (19)0.0079 (19)
C20.028 (2)0.042 (3)0.032 (2)0.0113 (19)0.0041 (18)0.0146 (19)
C30.038 (3)0.035 (2)0.030 (2)0.012 (2)0.0013 (18)0.0122 (18)
C40.022 (2)0.031 (2)0.040 (2)0.0008 (17)0.0061 (18)0.0135 (18)
C50.034 (2)0.037 (2)0.027 (2)0.0103 (19)0.0060 (18)0.0126 (18)
C60.036 (3)0.032 (2)0.038 (2)0.012 (2)0.0031 (19)0.0072 (19)
C70.040 (3)0.035 (2)0.061 (3)0.015 (2)0.004 (2)0.018 (2)
C80.035 (3)0.039 (3)0.076 (3)0.013 (2)0.015 (2)0.028 (2)
C90.043 (3)0.035 (2)0.038 (2)0.006 (2)0.009 (2)0.014 (2)
C100.054 (3)0.056 (3)0.051 (3)0.024 (3)0.004 (2)0.031 (2)
C110.037 (3)0.055 (3)0.049 (3)0.019 (2)0.009 (2)0.028 (2)
C120.078 (4)0.078 (4)0.063 (3)0.011 (3)0.006 (3)0.048 (3)
C130.029 (2)0.037 (2)0.031 (2)0.0076 (19)0.0051 (18)0.0118 (18)
C140.054 (4)0.069 (4)0.042 (3)0.014 (3)0.005 (3)0.016 (3)
C150.078 (5)0.075 (4)0.046 (3)0.018 (3)0.024 (3)0.000 (3)
C160.080 (4)0.062 (4)0.031 (3)0.018 (3)0.013 (3)0.008 (2)
C170.062 (4)0.047 (3)0.039 (2)0.023 (3)0.008 (2)0.018 (2)
C180.040 (3)0.034 (2)0.046 (3)0.004 (2)0.005 (2)0.014 (2)
C190.168 (8)0.079 (4)0.033 (3)0.055 (5)0.033 (4)0.024 (3)
C200.045 (3)0.046 (3)0.055 (3)0.017 (2)0.001 (2)0.024 (2)
C210.076 (6)0.243 (12)0.180 (8)0.021 (6)0.029 (6)0.167 (8)
C220.043 (3)0.035 (3)0.050 (3)0.011 (2)0.000 (2)0.005 (2)
C230.053 (3)0.033 (3)0.048 (3)0.003 (2)0.008 (3)0.006 (2)
C240.061 (5)0.136 (7)0.122 (6)0.018 (5)0.035 (4)0.023 (5)
O80.050 (2)0.0303 (17)0.071 (2)0.0060 (15)0.0021 (17)0.0193 (16)
O90.096 (3)0.054 (2)0.0351 (17)0.017 (2)0.0126 (18)0.0247 (16)
O100.034 (2)0.070 (2)0.0387 (17)0.0055 (17)0.0028 (15)0.0121 (16)
O110.051 (2)0.074 (3)0.0385 (18)0.030 (2)0.0055 (16)0.0053 (17)
O120.065 (3)0.068 (2)0.067 (2)0.0001 (19)0.0044 (19)0.0496 (19)
O130.077 (3)0.097 (3)0.089 (3)0.043 (3)0.023 (2)0.058 (3)
O140.069 (3)0.054 (2)0.065 (2)0.010 (2)0.012 (2)0.0180 (18)
N20.054 (3)0.0270 (19)0.0343 (18)0.0133 (18)0.0011 (17)0.0118 (16)
C250.048 (3)0.024 (2)0.037 (2)0.006 (2)0.005 (2)0.0136 (18)
C260.057 (3)0.041 (3)0.034 (2)0.025 (2)0.005 (2)0.014 (2)
C270.039 (3)0.032 (2)0.027 (2)0.0110 (19)0.0016 (18)0.0094 (17)
C280.047 (3)0.028 (2)0.029 (2)0.014 (2)0.0008 (19)0.0088 (18)
C290.036 (3)0.050 (3)0.032 (2)0.015 (2)0.003 (2)0.015 (2)
C300.032 (3)0.046 (3)0.040 (2)0.007 (2)0.013 (2)0.009 (2)
C310.026 (2)0.052 (3)0.056 (3)0.013 (2)0.004 (2)0.016 (2)
C320.042 (3)0.052 (3)0.031 (2)0.015 (2)0.001 (2)0.012 (2)
C330.045 (3)0.053 (3)0.027 (2)0.010 (2)0.012 (2)0.004 (2)
C340.031 (3)0.055 (3)0.038 (2)0.013 (2)0.006 (2)0.014 (2)
C350.038 (3)0.034 (2)0.029 (2)0.012 (2)0.0037 (19)0.0085 (18)
C360.060 (4)0.136 (6)0.060 (4)0.050 (4)0.014 (3)0.009 (4)
C370.035 (3)0.033 (2)0.028 (2)0.0094 (19)0.0010 (18)0.0092 (18)
C380.046 (3)0.040 (3)0.031 (2)0.013 (2)0.003 (2)0.0100 (19)
C390.044 (3)0.043 (3)0.046 (3)0.012 (2)0.003 (2)0.022 (2)
C400.046 (3)0.050 (3)0.047 (3)0.002 (2)0.008 (2)0.032 (2)
C410.055 (3)0.068 (4)0.039 (3)0.020 (3)0.006 (2)0.025 (3)
C420.065 (4)0.040 (3)0.036 (2)0.019 (3)0.003 (2)0.009 (2)
C430.047 (4)0.160 (7)0.105 (5)0.014 (4)0.008 (3)0.108 (5)
C440.066 (4)0.053 (3)0.045 (3)0.001 (3)0.012 (3)0.018 (2)
C450.152 (8)0.095 (5)0.058 (4)0.042 (5)0.027 (4)0.010 (4)
C460.053 (3)0.039 (3)0.055 (3)0.016 (2)0.013 (2)0.025 (2)
C470.074 (4)0.045 (3)0.046 (3)0.027 (3)0.009 (3)0.023 (2)
C480.098 (6)0.083 (5)0.121 (6)0.004 (4)0.051 (5)0.029 (4)
Geometric parameters (Å, º) top
O1—C11.403 (6)C18—H180.93
O2—C21.216 (6)C19—H19A0.96
O3—C51.235 (5)C19—H19B0.96
O4—C91.369 (6)C19—H19C0.96
O4—C121.437 (9)C20—H20B0.97
O5—C161.365 (6)C20—H20A0.97
O5—C191.427 (9)C21—H21C0.96
O6—C231.187 (7)C21—H21A0.96
O7—C231.306 (7)C21—H21B0.96
O7—C241.443 (10)C22—H22A0.97
O1—H10.82C22—H22B0.97
O8—C251.385 (7)C24—H24C0.96
O9—C261.219 (6)C24—H24B0.96
O10—C291.233 (7)C24—H24A0.96
O11—C361.408 (9)C25—C461.533 (7)
O11—C321.361 (6)C25—C261.550 (6)
O12—C401.368 (7)C26—C271.440 (7)
O12—C431.435 (8)C27—C291.468 (6)
O13—C471.194 (7)C27—C281.407 (5)
O14—C481.462 (11)C28—C371.448 (6)
O14—C471.317 (7)C29—C351.495 (6)
O8—H8A0.82C30—C351.378 (8)
N1—C41.332 (6)C30—C311.385 (7)
N1—C11.467 (5)C31—C321.374 (7)
N1—C201.472 (6)C32—C331.384 (8)
N2—C251.484 (6)C33—C341.377 (7)
N2—C441.476 (6)C34—C351.397 (6)
N2—C281.354 (6)C37—C381.391 (7)
C1—C221.519 (7)C37—C421.392 (6)
C1—C21.537 (8)C38—C391.373 (7)
C2—C31.448 (6)C39—C401.383 (7)
C3—C41.403 (6)C40—C411.374 (8)
C3—C51.446 (6)C41—C421.382 (8)
C4—C131.480 (6)C44—C451.450 (8)
C5—C61.493 (6)C46—C471.496 (8)
C6—C71.390 (7)C30—H300.93
C6—C111.380 (7)C31—H310.93
C7—C81.380 (7)C33—H330.93
C8—C91.372 (8)C34—H340.93
C9—C101.382 (8)C36—H36A0.96
C10—C111.376 (7)C36—H36B0.96
C13—C181.370 (7)C36—H36C0.96
C13—C141.381 (7)C38—H380.93
C14—C151.372 (7)C39—H390.93
C15—C161.393 (9)C41—H410.93
C16—C171.366 (8)C42—H420.93
C17—C181.391 (6)C43—H43A0.96
C20—C211.456 (11)C43—H43B0.96
C22—C231.508 (8)C43—H43C0.96
C7—H70.93C44—H44A0.97
C8—H80.93C44—H44B0.97
C10—H100.93C45—H45A0.96
C11—H110.93C45—H45B0.96
C12—H12B0.96C45—H45C0.96
C12—H12C0.96C46—H46A0.97
C12—H12A0.96C46—H46B0.97
C14—H140.93C48—H48A0.96
C15—H150.93C48—H48B0.96
C17—H170.93C48—H48C0.96
O1···O22.972 (5)C34···H43Biv3.0872
O1···O10i2.844 (5)C36···H43Cii2.6944
O1···C213.294 (11)C36···H312.5083
O2···C63.122 (6)C36···H45Bix2.9933
O2···C73.000 (6)C37···H44B2.5429
O2···O12.972 (5)C38···H183.0289
O2···C43ii3.159 (8)C39···H182.9679
O3···C263.418 (7)C40···H21Cv3.0882
O3···O82.754 (5)C40···H21Av3.0959
O3···C253.318 (6)C41···H43C2.8094
O3···C133.040 (5)C41···H21Cv2.9226
O3···C143.193 (6)C41···H43B2.7200
O6···C43.123 (7)C42···H44B2.7750
O6···N12.803 (6)C43···H412.5386
O6···C203.350 (7)C43···H33viii2.8618
O8···O92.930 (5)C44···H8A2.8828
O8···C20iii3.355 (7)C45···H46B3.0698
O8···O32.754 (5)C46···H45B3.0455
O9···O82.930 (5)C47···H39iii3.0922
O9···C19iv3.211 (7)H1···O10i2.0369
O9···C303.255 (6)H1···C29i2.9999
O9···C353.258 (6)H1···C34i3.0430
O10···C373.200 (5)H1···H21B2.5184
O10···C1v3.401 (7)H1···H34i2.4935
O10···O1v2.844 (5)H7···O22.7597
O10···C383.361 (6)H7···C22.7615
O12···C47vi3.389 (7)H7···C32.7087
O13···N23.012 (7)H8A···O31.9456
O13···C283.329 (7)H8A···C52.9833
O14···C263.306 (7)H8A···C442.8828
O1···H21B2.7180H8A···H44A2.3481
O1···H12Cvi2.5426H10···H22Aiii2.5048
O2···H312.6380H10···C122.5256
O2···H22B2.7639H10···H12B2.1790
O2···H72.7597H10···O5iv2.9103
O2···H43Bii2.7723H10···H12C2.4735
O3···H112.6292H11···O92.7254
O3···H302.7619H11···O32.6292
O3···H8A1.9456H12A···O13ii2.7509
O4···H42ii2.8582H12A···H45Cii2.4511
O4···H24Avii2.5409H12B···C102.6824
O4···H45Cii2.6097H12B···C15iv3.0023
O5···H10viii2.9103H12B···H15iv2.2302
O6···H382.7684H12B···H102.1790
O6···H24C2.6171H12C···O1iii2.5426
O6···H46Avi2.7927H12C···C102.8360
O6···H24B2.5380H12C···H102.4735
O7···H19Aix2.8519H14···C33.0603
O8···H20Aiii2.6403H14···H48Bi2.2997
O8···H44A2.4489H15···H12Bviii2.2302
O9···H112.7254H15···C12viii3.0548
O9···H46A2.8358H17···H19B2.3168
O9···H19Aiv2.4763H17···C192.5187
O10···H342.6600H17···H19C2.3123
O10···H1v2.0369H18···C392.9679
O11···H45Bix2.5573H18···C383.0289
O11···H46Bix2.7836H18···C203.0266
O12···H48Cvi2.7584H18···H20B2.3004
O12···H33viii2.7053H19A···O9viii2.4763
O13···H12Ax2.7509H19A···O7xi2.8519
O13···H48B2.5989H19B···C172.7403
O13···H48C2.6247H19B···H172.3168
O14···H39iii2.6245H19C···C31viii2.9611
N1···O62.803 (6)H19C···C172.7581
N2···O133.012 (7)H19C···C32viii3.0448
C1···O10i3.401 (7)H19C···H172.3123
C2···C73.169 (8)H20A···O8vi2.6403
C4···C233.525 (7)H20A···C222.7606
C4···O63.123 (7)H20A···H22A2.2571
C5···C143.398 (6)H20B···H182.3004
C6···O23.122 (6)H20B···C132.7158
C7···O23.000 (6)H20B···C182.5781
C7···C23.169 (8)H20B···H36Aviii2.5036
C13···O33.040 (5)H21A···H36Aviii2.5227
C13···C213.542 (12)H21A···C40i3.0959
C14···C53.398 (6)H21B···O12.7180
C14···O33.193 (6)H21B···H12.5184
C16···C443.561 (9)H21C···C40i3.0882
C18···C203.239 (7)H21C···C133.0685
C18···C383.516 (8)H21C···C41i2.9226
C19···O9viii3.211 (7)H22A···H10vi2.5048
C20···C183.239 (7)H22A···C202.9002
C20···O8vi3.355 (7)H22A···H20A2.2571
C20···O63.350 (7)H22B···O22.7639
C21···C41i3.571 (11)H24A···C12xii2.9589
C21···C39i3.533 (11)H24A···O4xii2.5409
C21···C133.542 (12)H24B···O62.5380
C21···O13.294 (11)H24C···O62.6171
C21···C40i3.394 (11)H30···O32.7619
C23···C43.525 (7)H30···C52.8450
C25···O33.318 (6)H30···C262.8158
C26···C303.247 (7)H30···C272.6143
C26···O143.306 (7)H31···O22.6380
C26···O33.418 (7)H31···C362.5083
C27···C473.439 (7)H31···H36B2.2748
C28···C473.411 (7)H31···H36C2.3196
C28···O133.329 (7)H33···O12iv2.7053
C29···C383.290 (7)H33···C43iv2.8618
C30···O93.255 (6)H34···O102.6600
C30···C263.247 (7)H34···H1v2.4935
C33···C43iv3.581 (9)H34···H43Biv2.5212
C35···O93.258 (6)H36A···C21iv3.0735
C37···O103.200 (5)H36A···H20Biv2.5036
C38···O103.361 (6)H36A···H21Aiv2.5227
C38···C293.290 (7)H36B···C312.7117
C38···C183.516 (8)H36B···H312.2748
C39···C21v3.533 (11)H36B···H43Cii2.5751
C40···C21v3.394 (11)H36C···C312.7418
C41···C21v3.571 (11)H36C···H312.3196
C42···C443.263 (9)H36C···H43Cii2.3946
C43···C33viii3.581 (9)H38···O62.7684
C43···O2x3.159 (8)H38···C272.9593
C44···C423.263 (9)H38···C292.9551
C44···C163.561 (9)H39···O14vi2.6245
C45···C463.589 (9)H39···C47vi3.0922
C46···C453.589 (9)H41···C432.5386
C47···C283.411 (7)H41···H43B2.2523
C47···O12iii3.389 (7)H41···H43C2.4155
C47···C273.439 (7)H42···O4x2.8582
C2···H72.7615H42···H45C2.5215
C3···H72.7087H43B···O2x2.7723
C3···H143.0603H43B···C34viii3.0872
C5···H8A2.9833H43B···C412.7200
C5···H302.8450H43B···H34viii2.5212
C10···H12B2.6824H43B···H412.2523
C10···H12C2.8360H43C···C36x2.6944
C12···H45Cii2.9783H43C···C412.8094
C12···H24Avii2.9589H43C···H36Bx2.5751
C12···H15iv3.0548H43C···H36Cx2.3946
C12···H102.5256H43C···H412.4155
C13···H21C3.0685H44A···O82.4489
C13···H20B2.7158H44A···H8A2.3481
C14···H48Bi3.0412H44B···C162.9760
C15···H12Bviii3.0023H44B···C172.8228
C16···H44B2.9760H44B···C372.5429
C17···H19C2.7581H44B···C422.7750
C17···H19B2.7403H45B···O11xi2.5573
C17···H44B2.8228H45B···C36xi2.9933
C18···H20B2.5781H45B···C463.0455
C19···H172.5187H45B···H46B2.3456
C20···H22A2.9002H45C···O4x2.6097
C20···H183.0266H45C···C12x2.9783
C21···H36Aviii3.0735H45C···H12Ax2.4511
C22···H20A2.7606H45C···H422.5215
C26···H302.8158H46A···O6iii2.7927
C27···H302.6143H46A···O92.8358
C27···H382.9593H46B···O11xi2.7836
C29···H1v2.9999H46B···C453.0698
C29···H382.9551H46B···H45B2.3456
C31···H36C2.7418H48B···O132.5989
C31···H36B2.7117H48B···C14v3.0412
C31···H19Civ2.9611H48B···H14v2.2997
C32···H19Civ3.0448H48C···O12iii2.7584
C34···H1v3.0430H48C···O132.6247
C9—O4—C12117.3 (5)C1—C22—H22A108.68
C16—O5—C19117.8 (5)H24B—C24—H24C109.47
C23—O7—C24116.4 (5)O7—C24—H24B109.45
C1—O1—H1109.47O7—C24—H24C109.50
C32—O11—C36117.2 (4)O7—C24—H24A109.52
C40—O12—C43117.3 (5)H24A—C24—H24C109.45
C47—O14—C48116.0 (5)H24A—C24—H24B109.44
C25—O8—H8A109.46O8—C25—N2112.4 (4)
C1—N1—C20122.0 (4)O8—C25—C26112.3 (4)
C4—N1—C20127.9 (4)N2—C25—C26102.3 (4)
C1—N1—C4110.1 (4)N2—C25—C46112.1 (4)
C25—N2—C44121.3 (4)O8—C25—C46107.3 (4)
C25—N2—C28110.2 (3)C26—C25—C46110.5 (4)
C28—N2—C44125.0 (4)O9—C26—C27131.3 (4)
O1—C1—C2112.3 (4)C25—C26—C27106.9 (4)
O1—C1—C22106.7 (4)O9—C26—C25121.7 (5)
N1—C1—C22112.0 (4)C26—C27—C29126.7 (4)
O1—C1—N1110.7 (4)C28—C27—C29125.5 (4)
C2—C1—C22112.2 (4)C26—C27—C28107.7 (4)
N1—C1—C2103.0 (4)N2—C28—C37121.1 (3)
C1—C2—C3106.9 (4)C27—C28—C37126.4 (4)
O2—C2—C3132.0 (5)N2—C28—C27112.3 (4)
O2—C2—C1121.1 (4)O10—C29—C35120.1 (4)
C4—C3—C5127.2 (3)C27—C29—C35117.4 (4)
C2—C3—C5125.9 (3)O10—C29—C27122.4 (4)
C2—C3—C4106.5 (4)C31—C30—C35120.7 (4)
N1—C4—C13120.3 (4)C30—C31—C32119.6 (5)
C3—C4—C13126.1 (4)O11—C32—C31125.0 (5)
N1—C4—C3113.5 (4)C31—C32—C33120.1 (4)
O3—C5—C6119.7 (4)O11—C32—C33114.9 (4)
O3—C5—C3121.8 (4)C32—C33—C34120.5 (4)
C3—C5—C6118.5 (3)C33—C34—C35119.5 (5)
C7—C6—C11118.3 (4)C29—C35—C34120.3 (5)
C5—C6—C11120.0 (4)C30—C35—C34119.4 (4)
C5—C6—C7121.7 (4)C29—C35—C30120.2 (4)
C6—C7—C8120.8 (5)C28—C37—C42122.4 (4)
C7—C8—C9120.1 (5)C38—C37—C42117.5 (4)
O4—C9—C10124.3 (5)C28—C37—C38120.1 (4)
O4—C9—C8116.0 (5)C37—C38—C39121.2 (4)
C8—C9—C10119.7 (5)C38—C39—C40120.2 (5)
C9—C10—C11120.1 (5)O12—C40—C41125.3 (4)
C6—C11—C10121.0 (5)C39—C40—C41119.8 (5)
C14—C13—C18118.7 (4)O12—C40—C39114.9 (5)
C4—C13—C14119.6 (4)C40—C41—C42119.6 (5)
C4—C13—C18121.6 (4)C37—C42—C41121.6 (5)
C13—C14—C15120.4 (6)N2—C44—C45117.1 (6)
C14—C15—C16120.5 (6)C25—C46—C47113.6 (4)
C15—C16—C17119.5 (5)O13—C47—C46125.1 (5)
O5—C16—C15115.7 (6)O14—C47—C46111.0 (4)
O5—C16—C17124.7 (6)O13—C47—O14123.8 (6)
C16—C17—C18119.4 (5)C31—C30—H30119.62
C13—C18—C17121.5 (5)C35—C30—H30119.67
N1—C20—C21114.1 (6)C30—C31—H31120.20
C1—C22—C23114.5 (4)C32—C31—H31120.16
O6—C23—O7122.8 (6)C32—C33—H33119.72
O7—C23—C22112.2 (5)C34—C33—H33119.75
O6—C23—C22124.8 (5)C33—C34—H34120.27
C8—C7—H7119.59C35—C34—H34120.20
C6—C7—H7119.61O11—C36—H36A109.48
C9—C8—H8120.03O11—C36—H36B109.44
C7—C8—H8119.90O11—C36—H36C109.50
C11—C10—H10119.97H36A—C36—H36B109.46
C9—C10—H10119.97H36A—C36—H36C109.46
C6—C11—H11119.42H36B—C36—H36C109.50
C10—C11—H11119.55C37—C38—H38119.44
H12A—C12—H12B109.46C39—C38—H38119.36
O4—C12—H12C109.51C38—C39—H39119.82
O4—C12—H12B109.50C40—C39—H39119.94
O4—C12—H12A109.37C40—C41—H41120.15
H12B—C12—H12C109.52C42—C41—H41120.21
H12A—C12—H12C109.47C37—C42—H42119.24
C13—C14—H14119.80C41—C42—H42119.21
C15—C14—H14119.77O12—C43—H43A109.49
C16—C15—H15119.80O12—C43—H43B109.46
C14—C15—H15119.75O12—C43—H43C109.44
C16—C17—H17120.36H43A—C43—H43B109.52
C18—C17—H17120.28H43A—C43—H43C109.49
C17—C18—H18119.24H43B—C43—H43C109.43
C13—C18—H18119.23N2—C44—H44A108.02
H19A—C19—H19C109.43N2—C44—H44B108.02
H19B—C19—H19C109.48C45—C44—H44A108.05
H19A—C19—H19B109.47C45—C44—H44B108.03
O5—C19—H19B109.50H44A—C44—H44B107.25
O5—C19—H19C109.48C44—C45—H45A109.45
O5—C19—H19A109.47C44—C45—H45B109.47
N1—C20—H20A108.80C44—C45—H45C109.45
N1—C20—H20B108.76H45A—C45—H45B109.49
C21—C20—H20B108.73H45A—C45—H45C109.48
H20A—C20—H20B107.62H45B—C45—H45C109.49
C21—C20—H20A108.69C25—C46—H46A108.80
C20—C21—H21B109.44C25—C46—H46B108.78
C20—C21—H21A109.49C47—C46—H46A108.89
H21A—C21—H21C109.51C47—C46—H46B108.83
C20—C21—H21C109.41H46A—C46—H46B107.75
H21A—C21—H21B109.53O14—C48—H48A109.48
H21B—C21—H21C109.44O14—C48—H48B109.49
C23—C22—H22B108.58O14—C48—H48C109.44
C23—C22—H22A108.68H48A—C48—H48B109.47
C1—C22—H22B108.62H48A—C48—H48C109.48
H22A—C22—H22B107.62H48B—C48—H48C109.47
C12—O4—C9—C8167.1 (5)C6—C7—C8—C91.6 (8)
C12—O4—C9—C1012.9 (7)C7—C8—C9—C101.4 (8)
C19—O5—C16—C15177.4 (6)C7—C8—C9—O4178.6 (5)
C19—O5—C16—C170.5 (10)C8—C9—C10—C111.5 (8)
C24—O7—C23—O60.3 (9)O4—C9—C10—C11178.6 (5)
C24—O7—C23—C22176.5 (6)C9—C10—C11—C61.6 (7)
C36—O11—C32—C33177.6 (5)C18—C13—C14—C150.9 (8)
C36—O11—C32—C312.1 (8)C14—C13—C18—C170.0 (8)
C43—O12—C40—C417.5 (8)C4—C13—C18—C17177.6 (5)
C43—O12—C40—C39172.1 (5)C4—C13—C14—C15176.7 (5)
C48—O14—C47—O132.9 (8)C13—C14—C15—C161.4 (10)
C48—O14—C47—C46178.5 (5)C14—C15—C16—O5178.0 (6)
C4—N1—C1—O1121.1 (4)C14—C15—C16—C170.9 (11)
C20—N1—C4—C3175.3 (5)C15—C16—C17—C180.0 (10)
C20—N1—C1—C2176.4 (4)O5—C16—C17—C18176.8 (6)
C4—N1—C1—C22120.0 (5)C16—C17—C18—C130.5 (9)
C1—N1—C4—C31.7 (6)C1—C22—C23—O643.7 (8)
C20—N1—C1—O156.1 (6)C1—C22—C23—O7139.6 (5)
C20—N1—C1—C2262.8 (6)C46—C25—C26—O964.5 (6)
C1—N1—C4—C13178.4 (4)C46—C25—C26—C27111.9 (4)
C4—N1—C1—C20.8 (5)O8—C25—C46—C47178.7 (4)
C20—N1—C4—C134.6 (7)N2—C25—C26—C277.6 (5)
C1—N1—C20—C2194.2 (7)O8—C25—C26—C27128.3 (4)
C4—N1—C20—C2182.5 (7)N2—C25—C26—O9176.1 (5)
C44—N2—C28—C27156.0 (4)O8—C25—C26—O955.4 (7)
C28—N2—C25—C46111.9 (4)C26—C25—C46—C4758.5 (5)
C44—N2—C25—C4688.2 (5)N2—C25—C46—C4754.9 (5)
C44—N2—C25—O832.7 (6)C25—C26—C27—C286.2 (5)
C25—N2—C28—C273.1 (6)O9—C26—C27—C290.4 (9)
C28—N2—C25—O8127.2 (4)C25—C26—C27—C29175.5 (5)
C44—N2—C25—C26153.4 (4)O9—C26—C27—C28177.9 (6)
C28—N2—C44—C45117.6 (6)C29—C27—C28—C376.5 (8)
C28—N2—C25—C266.5 (5)C28—C27—C29—C35131.5 (5)
C25—N2—C28—C37177.5 (4)C26—C27—C28—C37171.9 (5)
C44—N2—C28—C3718.5 (7)C26—C27—C28—N22.2 (6)
C25—N2—C44—C4585.5 (7)C28—C27—C29—O1045.8 (8)
N1—C1—C2—O2177.5 (5)C26—C27—C29—C3546.5 (7)
N1—C1—C22—C2354.6 (6)C26—C27—C29—O10136.2 (5)
O1—C1—C22—C23175.9 (4)C29—C27—C28—N2179.5 (4)
C22—C1—C2—O256.9 (6)C27—C28—C37—C42130.5 (5)
C2—C1—C22—C2360.7 (5)N2—C28—C37—C4255.9 (7)
C22—C1—C2—C3120.9 (4)C27—C28—C37—C3852.9 (7)
O1—C1—C2—C3118.9 (4)N2—C28—C37—C38120.7 (5)
O1—C1—C2—O263.3 (6)C27—C29—C35—C3030.0 (7)
N1—C1—C2—C30.3 (5)O10—C29—C35—C3429.2 (7)
C1—C2—C3—C5173.6 (4)C27—C29—C35—C34153.4 (5)
O2—C2—C3—C53.9 (8)O10—C29—C35—C30147.4 (5)
O2—C2—C3—C4176.3 (5)C31—C30—C35—C29174.3 (5)
C1—C2—C3—C41.2 (5)C35—C30—C31—C323.0 (8)
C2—C3—C5—C635.6 (6)C31—C30—C35—C342.4 (7)
C4—C3—C5—O326.0 (7)C30—C31—C32—O11178.7 (5)
C4—C3—C5—C6153.5 (4)C30—C31—C32—C331.6 (8)
C5—C3—C4—C135.9 (7)O11—C32—C33—C34179.3 (5)
C5—C3—C4—N1174.1 (4)C31—C32—C33—C340.4 (8)
C2—C3—C4—N11.8 (5)C32—C33—C34—C351.0 (8)
C2—C3—C4—C13178.2 (4)C33—C34—C35—C300.4 (7)
C2—C3—C5—O3144.8 (4)C33—C34—C35—C29176.3 (5)
C3—C4—C13—C1458.8 (7)C42—C37—C38—C390.8 (7)
N1—C4—C13—C14121.2 (5)C38—C37—C42—C411.5 (8)
N1—C4—C13—C1861.3 (6)C28—C37—C42—C41178.1 (5)
C3—C4—C13—C18118.7 (5)C28—C37—C38—C39175.9 (5)
O3—C5—C6—C7147.2 (4)C37—C38—C39—C401.6 (8)
O3—C5—C6—C1130.9 (6)C38—C39—C40—O12179.7 (5)
C3—C5—C6—C732.3 (6)C38—C39—C40—C410.0 (8)
C3—C5—C6—C11149.6 (4)O12—C40—C41—C42178.1 (5)
C7—C6—C11—C101.7 (7)C39—C40—C41—C422.2 (8)
C5—C6—C7—C8176.4 (4)C40—C41—C42—C373.0 (9)
C5—C6—C11—C10176.4 (4)C25—C46—C47—O1372.5 (6)
C11—C6—C7—C81.7 (7)C25—C46—C47—O14106.1 (5)
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z1; (iii) x, y1, z; (iv) x, y, z1; (v) x1, y, z; (vi) x, y+1, z; (vii) x+1, y1, z; (viii) x, y, z+1; (ix) x, y+1, z1; (x) x1, y, z+1; (xi) x, y1, z+1; (xii) x1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O10i0.822.042.844 (5)168
O8—H8A···O30.821.952.754 (5)169
C12—H12C···O1iii0.962.543.434 (7)155
C19—H19A···O9viii0.962.483.211 (7)133
C24—H24A···O4xii0.962.543.440 (10)156
C44—H44A···O80.972.452.869 (6)106
C45—H45B···O11xi0.962.563.471 (10)159
Symmetry codes: (i) x+1, y, z; (iii) x, y1, z; (viii) x, y, z+1; (xi) x, y1, z+1; (xii) x1, y+1, z.

Experimental details

Crystal data
Chemical formulaC24H25NO7
Mr439.45
Crystal system, space groupTriclinic, 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)
V3)1129.4 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.52 × 0.26 × 0.20
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionPart of the refinement model (ΔF)
[Parkin et al., 1995; cubic fit to sin(θ)/λ with 24 parameters]
Tmin, Tmax0.952, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections
6035, 6035, 4369
Rint0.000
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.127, 1.11
No. of reflections6035
No. of parameters577
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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).

Selected geometric parameters (Å, º) top
O1—C11.403 (6)O11—C361.408 (9)
O2—C21.216 (6)O11—C321.361 (6)
O3—C51.235 (5)O12—C401.368 (7)
O4—C91.369 (6)O12—C431.435 (8)
O4—C121.437 (9)O13—C471.194 (7)
O5—C161.365 (6)O14—C481.462 (11)
O5—C191.427 (9)O14—C471.317 (7)
O6—C231.187 (7)N1—C41.332 (6)
O7—C231.306 (7)N1—C11.467 (5)
O7—C241.443 (10)N1—C201.472 (6)
O8—C251.385 (7)N2—C251.484 (6)
O9—C261.219 (6)N2—C441.476 (6)
O10—C291.233 (7)N2—C281.354 (6)
C9—O4—C12117.3 (5)O5—C16—C15115.7 (6)
C16—O5—C19117.8 (5)O5—C16—C17124.7 (6)
C23—O7—C24116.4 (5)N1—C20—C21114.1 (6)
C32—O11—C36117.2 (4)O6—C23—O7122.8 (6)
C40—O12—C43117.3 (5)O7—C23—C22112.2 (5)
C47—O14—C48116.0 (5)O6—C23—C22124.8 (5)
C1—N1—C20122.0 (4)O8—C25—N2112.4 (4)
C4—N1—C20127.9 (4)O8—C25—C26112.3 (4)
C1—N1—C4110.1 (4)N2—C25—C26102.3 (4)
C25—N2—C44121.3 (4)N2—C25—C46112.1 (4)
C25—N2—C28110.2 (3)O8—C25—C46107.3 (4)
C28—N2—C44125.0 (4)O9—C26—C27131.3 (4)
O1—C1—C2112.3 (4)O9—C26—C25121.7 (5)
O1—C1—C22106.7 (4)N2—C28—C37121.1 (3)
N1—C1—C22112.0 (4)N2—C28—C27112.3 (4)
O1—C1—N1110.7 (4)O10—C29—C35120.1 (4)
N1—C1—C2103.0 (4)O10—C29—C27122.4 (4)
O2—C2—C3132.0 (5)O11—C32—C31125.0 (5)
O2—C2—C1121.1 (4)O11—C32—C33114.9 (4)
N1—C4—C13120.3 (4)O12—C40—C41125.3 (4)
N1—C4—C3113.5 (4)O12—C40—C39114.9 (5)
O3—C5—C6119.7 (4)N2—C44—C45117.1 (6)
O3—C5—C3121.8 (4)O13—C47—C46125.1 (5)
O4—C9—C10124.3 (5)O14—C47—C46111.0 (4)
O4—C9—C8116.0 (5)O13—C47—O14123.8 (6)
C24—O7—C23—O60.3 (9)O1—C1—C2—C3118.9 (4)
C24—O7—C23—C22176.5 (6)O1—C1—C2—O263.3 (6)
C48—O14—C47—O132.9 (8)O2—C2—C3—C4176.3 (5)
C48—O14—C47—C46178.5 (5)C1—C22—C23—O643.7 (8)
C4—N1—C1—O1121.1 (4)O8—C25—C26—C27128.3 (4)
C1—N1—C20—C2194.2 (7)N2—C25—C26—O9176.1 (5)
C4—N1—C20—C2182.5 (7)O8—C25—C26—O955.4 (7)
C28—N2—C25—O8127.2 (4)C26—C25—C46—C4758.5 (5)
C28—N2—C44—C45117.6 (6)N2—C25—C46—C4754.9 (5)
C25—N2—C44—C4585.5 (7)O9—C26—C27—C28177.9 (6)
N1—C1—C2—O2177.5 (5)C25—C46—C47—O1372.5 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O10i0.822.042.844 (5)168
O8—H8A···O30.821.952.754 (5)169
C12—H12C···O1ii0.962.543.434 (7)155
C19—H19A···O9iii0.962.483.211 (7)133
C24—H24A···O4iv0.962.543.440 (10)156
C44—H44A···O80.972.452.869 (6)106
C45—H45B···O11v0.962.563.471 (10)159
Symmetry codes: (i) x+1, y, z; (ii) x, y1, z; (iii) x, y, z+1; (iv) x1, y+1, z; (v) x, y1, z+1.
 

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