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The title compound, C24H26N2O7, is an inter­mediate in the resolution of a tertiary alcohol using a chiral isocyanate reagent. On the basis of the unchanging S configuration of the chiral C atom introduced by the isocyanate reagent, the chiral centre on the tricyclo ring system is shown to adopt an S configuration. In the crystal structure, N—H...O hydrogen bonds link the mol­ecules into chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038731/bi2220sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038731/bi2220Isup2.hkl
Contains datablock I

CCDC reference: 663676

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.034
  • wR factor = 0.087
  • Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.81 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.22 Ratio PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C12 .. 2.99 Ang.
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 27.50 From the CIF: _reflns_number_total 2612 Count of symmetry unique reflns 2657 Completeness (_total/calc) 98.31% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17 = . S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The method for resolution of a tertiary alcohol using a chiral isocyanate reagent has been widely applied (Gibbs et al., 1989). The title compound is a key intermediate in the resolution process of alcohol 1 using the (S)-isocyanate 2 (Scheme 2).

On the basis of the unchanging S configuration of C17, the molecular structure (Figure 1) indicates that the chiral C atom C3 adopts an S configuration. The six-membered lactone ring is twisted with an O1/C2/C3/C4 torsion angle of -21.4 (3) °. The pyrrole ring is also twisted, with a N1/C6/C7/C8 torsion angle of 22.3 (2) °. N—H···O hydrogen bonds exist between molecules, linking them into chains along the c axis.

Related literature top

For related literature, see: Duggan & Imagire (1989); Gibbs et al. (1989).

Experimental top

The (S)-isocyanate 2 (2.0 mmol) was added to a mixture of alcohol 1 (1.0 mmol) and reagent grade CuCl (0.2 mmol) in dry CH2Cl2 (12 ml) at room temperature (Scheme 2; Duggan & Imagire, 1989). After stirring for 12 h, the reaction mixture was filtered and the filtrate was diluted with CH2Cl2 (20 ml), washed with H2O (20 ml) and brine (20 ml), dried over MgSO4 and concentrated. The crude product (0.43 g, 94%) was recrystallized from 2-propanol (31 ml) to yield a white powder (m.p. 485 K). Crystals suitable for X-ray analysis were obtained from ethyl acetate.

Refinement top

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å and N—H = 0.88 Å, and with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. The methyl groups were allowed to rotate about their local threefold axes. In the absence of significant anomalous scattering effects, Friedel pairs have been merged as equivalent data. The absolute structure was assigned on the basis of the unchanging chiral centre C17, originating from the isocyanate reactant.

Structure description top

The method for resolution of a tertiary alcohol using a chiral isocyanate reagent has been widely applied (Gibbs et al., 1989). The title compound is a key intermediate in the resolution process of alcohol 1 using the (S)-isocyanate 2 (Scheme 2).

On the basis of the unchanging S configuration of C17, the molecular structure (Figure 1) indicates that the chiral C atom C3 adopts an S configuration. The six-membered lactone ring is twisted with an O1/C2/C3/C4 torsion angle of -21.4 (3) °. The pyrrole ring is also twisted, with a N1/C6/C7/C8 torsion angle of 22.3 (2) °. N—H···O hydrogen bonds exist between molecules, linking them into chains along the c axis.

For related literature, see: Duggan & Imagire (1989); Gibbs et al. (1989).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing displacement ellipsoids at 30% probability for non-H atoms.
[Figure 2] Fig. 2. Unit-cell contents viewed along the b axis.
[Figure 3] Fig. 3. The formation of the title compound.
(4'S)-4'-Ethyl-3',10'-dioxo-3',4',7',8'-tetrahydrospiro[1,3-dioxolane-2,6'- 1'H,6'H-pyrano[3,4-f]indolizin]-4'-yl N-(1-phenylethyl)carbamate top
Crystal data top
C24H26N2O7F(000) = 480
Mr = 454.47Dx = 1.352 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2722 reflections
a = 7.3998 (10) Åθ = 2.2–25.4°
b = 16.383 (2) ŵ = 0.10 mm1
c = 9.2162 (13) ÅT = 296 K
β = 92.322 (2)°Prism, colourless
V = 1116.4 (3) Å30.30 × 0.25 × 0.20 mm
Z = 2
Data collection top
Bruker SMART APEX II CCD
diffractometer
2612 independent reflections
Radiation source: fine-focus sealed tube2352 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
φ and ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 89
Tmin = 0.971, Tmax = 0.980k = 1821
7148 measured reflectionsl = 911
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034 w = 1/[σ2(Fo2) + (0.0485P)2 + 0.0587P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.087(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.21 e Å3
2612 reflectionsΔρmin = 0.13 e Å3
302 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.015 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Friedel pairs merged as equivalent data
Secondary atom site location: difference Fourier map
Crystal data top
C24H26N2O7V = 1116.4 (3) Å3
Mr = 454.47Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.3998 (10) ŵ = 0.10 mm1
b = 16.383 (2) ÅT = 296 K
c = 9.2162 (13) Å0.30 × 0.25 × 0.20 mm
β = 92.322 (2)°
Data collection top
Bruker SMART APEX II CCD
diffractometer
2612 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2352 reflections with I > 2σ(I)
Tmin = 0.971, Tmax = 0.980Rint = 0.023
7148 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0341 restraint
wR(F2) = 0.087H-atom parameters constrained
S = 1.06Δρmax = 0.21 e Å3
2612 reflectionsΔρmin = 0.13 e Å3
302 parametersAbsolute structure: Friedel pairs merged as equivalent data
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.9756 (3)0.86809 (10)0.37052 (17)0.0497 (4)
O21.0016 (3)0.90832 (11)0.14679 (19)0.0571 (5)
O30.8961 (2)0.75590 (10)0.03780 (15)0.0361 (3)
O40.6197 (2)0.46524 (11)0.2027 (2)0.0518 (4)
O50.8933 (2)0.44686 (10)0.31575 (17)0.0438 (4)
O60.8228 (2)0.68765 (11)0.66980 (16)0.0445 (4)
O71.1799 (2)0.74245 (12)0.13801 (17)0.0483 (4)
N10.7652 (2)0.59843 (11)0.48365 (19)0.0342 (4)
N21.1043 (3)0.69448 (13)0.0887 (2)0.0429 (5)
H21.01380.69190.15380.043 (7)*
C10.9037 (3)0.81619 (15)0.4800 (2)0.0415 (5)
H1A0.80130.84340.52120.050*
H1B0.99530.80900.55730.050*
C20.9466 (3)0.85775 (14)0.2281 (2)0.0395 (5)
C30.8317 (3)0.78525 (13)0.1735 (2)0.0337 (4)
C40.8214 (3)0.71695 (12)0.2830 (2)0.0314 (4)
C50.7784 (3)0.63660 (14)0.2365 (2)0.0343 (4)
H50.76610.62380.13830.041*
C60.7561 (3)0.57932 (13)0.3391 (2)0.0331 (4)
C70.7254 (3)0.48743 (13)0.3259 (3)0.0382 (5)
C80.6437 (3)0.46579 (16)0.4706 (3)0.0479 (6)
H8A0.51270.46820.46250.057*
H8B0.67980.41130.50120.057*
C90.7175 (3)0.52940 (15)0.5779 (3)0.0442 (6)
H9A0.62650.54530.64540.053*
H9B0.82300.50900.63230.053*
C100.8130 (3)0.67425 (14)0.5379 (2)0.0342 (4)
C110.8446 (3)0.73440 (13)0.4266 (2)0.0326 (4)
C120.9214 (4)0.43939 (19)0.1647 (3)0.0581 (7)
H12A0.99340.39150.14470.070*
H12B0.98150.48730.12810.070*
C130.7343 (5)0.4315 (2)0.0987 (3)0.0685 (9)
H13A0.72300.46130.00780.082*
H13B0.70460.37460.08040.082*
C140.6397 (3)0.81741 (16)0.1294 (2)0.0432 (5)
H14A0.64880.85180.04440.052*
H14B0.56400.77120.10180.052*
C150.5467 (3)0.86541 (17)0.2454 (3)0.0510 (6)
H15A0.61080.91550.26380.076*
H15B0.54560.83380.33300.076*
H15C0.42470.87730.21270.076*
C161.0725 (3)0.73094 (14)0.0376 (2)0.0357 (5)
C171.2862 (3)0.66796 (18)0.1258 (3)0.0493 (6)
H171.36940.71380.10830.059*
C181.3521 (6)0.5967 (3)0.0323 (3)0.0880 (13)
H18A1.26450.55350.03830.132*
H18B1.36800.61430.06680.132*
H18C1.46530.57740.06620.132*
C191.2817 (3)0.64878 (15)0.2861 (2)0.0378 (5)
C201.2066 (3)0.57611 (15)0.3382 (2)0.0424 (5)
H201.16240.53830.27320.051*
C211.1968 (4)0.55937 (18)0.4847 (3)0.0517 (7)
H211.14850.51000.51750.062*
C221.2572 (4)0.6144 (2)0.5813 (3)0.0611 (8)
H221.24880.60300.68030.073*
C231.3300 (4)0.6861 (2)0.5336 (3)0.0696 (9)
H231.37130.72370.60030.084*
C241.3436 (4)0.70394 (18)0.3862 (3)0.0558 (7)
H241.39450.75310.35470.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0722 (12)0.0424 (9)0.0346 (8)0.0192 (9)0.0029 (8)0.0057 (7)
O20.0855 (14)0.0408 (9)0.0462 (10)0.0161 (10)0.0177 (9)0.0003 (8)
O30.0421 (8)0.0407 (8)0.0254 (7)0.0030 (7)0.0020 (6)0.0044 (6)
O40.0513 (9)0.0465 (10)0.0567 (11)0.0033 (8)0.0082 (8)0.0087 (8)
O50.0487 (9)0.0429 (9)0.0396 (8)0.0118 (7)0.0007 (7)0.0048 (7)
O60.0530 (9)0.0532 (10)0.0274 (8)0.0067 (8)0.0001 (7)0.0026 (7)
O70.0462 (9)0.0642 (12)0.0339 (8)0.0019 (8)0.0043 (7)0.0097 (8)
N10.0365 (9)0.0356 (10)0.0306 (9)0.0042 (8)0.0044 (7)0.0025 (7)
N20.0400 (10)0.0571 (13)0.0313 (9)0.0084 (9)0.0022 (8)0.0104 (9)
C10.0527 (13)0.0394 (12)0.0324 (11)0.0061 (11)0.0010 (10)0.0039 (10)
C20.0478 (12)0.0348 (12)0.0363 (12)0.0035 (10)0.0083 (10)0.0043 (10)
C30.0405 (11)0.0331 (10)0.0274 (10)0.0012 (9)0.0020 (8)0.0041 (8)
C40.0326 (10)0.0323 (10)0.0295 (10)0.0019 (8)0.0021 (8)0.0033 (8)
C50.0413 (11)0.0341 (11)0.0274 (10)0.0003 (9)0.0010 (8)0.0046 (8)
C60.0326 (10)0.0322 (11)0.0344 (11)0.0026 (8)0.0008 (8)0.0044 (9)
C70.0394 (11)0.0310 (11)0.0441 (13)0.0014 (9)0.0010 (9)0.0002 (9)
C80.0508 (13)0.0394 (13)0.0545 (15)0.0010 (11)0.0133 (11)0.0048 (11)
C90.0528 (14)0.0399 (12)0.0408 (13)0.0058 (11)0.0130 (10)0.0095 (10)
C100.0339 (10)0.0393 (11)0.0295 (10)0.0065 (9)0.0019 (8)0.0020 (9)
C110.0343 (10)0.0357 (11)0.0278 (10)0.0018 (9)0.0016 (8)0.0045 (8)
C120.0686 (18)0.0605 (17)0.0456 (14)0.0120 (14)0.0076 (13)0.0118 (13)
C130.087 (2)0.0624 (19)0.0550 (16)0.0104 (16)0.0080 (15)0.0230 (15)
C140.0458 (12)0.0446 (13)0.0390 (12)0.0085 (10)0.0000 (10)0.0004 (10)
C150.0477 (13)0.0490 (14)0.0567 (15)0.0068 (12)0.0083 (11)0.0009 (12)
C160.0439 (11)0.0357 (11)0.0276 (10)0.0011 (9)0.0021 (9)0.0009 (9)
C170.0441 (13)0.0624 (17)0.0411 (13)0.0119 (11)0.0027 (10)0.0115 (12)
C180.110 (3)0.115 (3)0.0382 (15)0.065 (3)0.0092 (16)0.0031 (17)
C190.0324 (10)0.0446 (13)0.0365 (12)0.0058 (9)0.0046 (8)0.0024 (10)
C200.0445 (12)0.0438 (13)0.0390 (12)0.0037 (10)0.0025 (10)0.0011 (10)
C210.0482 (14)0.0552 (15)0.0512 (15)0.0099 (12)0.0054 (11)0.0172 (12)
C220.0525 (15)0.092 (2)0.0383 (14)0.0138 (15)0.0034 (12)0.0036 (14)
C230.0656 (18)0.093 (3)0.0515 (17)0.0036 (18)0.0146 (14)0.0258 (17)
C240.0545 (15)0.0497 (15)0.0633 (18)0.0088 (12)0.0033 (13)0.0010 (13)
Geometric parameters (Å, º) top
O1—C21.333 (3)C9—H9A0.970
O1—C11.438 (3)C9—H9B0.970
O2—C21.199 (3)C10—C111.448 (3)
O3—C161.369 (3)C12—C131.495 (5)
O3—C31.439 (2)C12—H12A0.970
O4—C71.400 (3)C12—H12B0.970
O4—C131.419 (4)C13—H13A0.970
O5—C71.416 (3)C13—H13B0.970
O5—C121.421 (3)C14—C151.515 (3)
O6—C101.235 (3)C14—H14A0.970
O7—C161.210 (3)C14—H14B0.970
N1—C61.368 (3)C15—H15A0.960
N1—C101.380 (3)C15—H15B0.960
N1—C91.478 (3)C15—H15C0.960
N2—C161.337 (3)C17—C191.510 (3)
N2—C171.468 (3)C17—C181.519 (4)
N2—H20.88C17—H170.980
C1—C111.487 (3)C18—H18A0.960
C1—H1A0.970C18—H18B0.960
C1—H1B0.970C18—H18C0.960
C2—C31.534 (3)C19—C241.382 (4)
C3—C41.511 (3)C19—C201.391 (3)
C3—C141.553 (3)C20—C211.377 (3)
C4—C111.358 (3)C20—H200.930
C4—C51.417 (3)C21—C221.356 (4)
C5—C61.347 (3)C21—H210.930
C5—H50.930C22—C231.359 (5)
C6—C71.527 (3)C22—H220.930
C7—C81.528 (3)C23—C241.390 (4)
C8—C91.523 (4)C23—H230.930
C8—H8A0.970C24—H240.930
C8—H8B0.970
C2—O1—C1124.53 (18)O5—C12—C13103.7 (2)
C16—O3—C3116.79 (16)O5—C12—H12A111.0
C7—O4—C13108.6 (2)C13—C12—H12A111.0
C7—O5—C12105.57 (19)O5—C12—H12B111.0
C6—N1—C10124.12 (18)C13—C12—H12B111.0
C6—N1—C9113.22 (18)H12A—C12—H12B109.0
C10—N1—C9122.67 (18)O4—C13—C12105.1 (2)
C16—N2—C17122.03 (19)O4—C13—H13A110.7
C16—N2—H2117.3C12—C13—H13A110.7
C17—N2—H2120.3O4—C13—H13B110.7
O1—C1—C11114.38 (17)C12—C13—H13B110.7
O1—C1—H1A108.7H13A—C13—H13B108.8
C11—C1—H1A108.7C15—C14—C3115.36 (19)
O1—C1—H1B108.7C15—C14—H14A108.4
C11—C1—H1B108.7C3—C14—H14A108.4
H1A—C1—H1B107.6C15—C14—H14B108.4
O2—C2—O1118.8 (2)C3—C14—H14B108.4
O2—C2—C3121.9 (2)H14A—C14—H14B107.5
O1—C2—C3119.10 (18)C14—C15—H15A109.5
O3—C3—C4111.14 (17)C14—C15—H15B109.5
O3—C3—C2110.17 (16)H15A—C15—H15B109.5
C4—C3—C2113.39 (17)C14—C15—H15C109.5
O3—C3—C14102.54 (16)H15A—C15—H15C109.5
C4—C3—C14110.84 (18)H15B—C15—H15C109.5
C2—C3—C14108.18 (18)O7—C16—N2127.0 (2)
C11—C4—C5120.59 (19)O7—C16—O3123.32 (19)
C11—C4—C3119.16 (18)N2—C16—O3109.65 (18)
C5—C4—C3120.17 (18)N2—C17—C19107.78 (18)
C6—C5—C4117.85 (19)N2—C17—C18111.8 (3)
C6—C5—H5121.1C19—C17—C18112.9 (2)
C4—C5—H5121.1N2—C17—H17108.1
C5—C6—N1121.5 (2)C19—C17—H17108.1
C5—C6—C7130.8 (2)C18—C17—H17108.1
N1—C6—C7107.74 (18)C17—C18—H18A109.5
O4—C7—O5106.74 (19)C17—C18—H18B109.5
O4—C7—C6113.41 (19)H18A—C18—H18B109.5
O5—C7—C6109.87 (18)C17—C18—H18C109.5
O4—C7—C8114.8 (2)H18A—C18—H18C109.5
O5—C7—C8109.14 (19)H18B—C18—H18C109.5
C6—C7—C8102.82 (19)C24—C19—C20117.9 (2)
C9—C8—C7105.3 (2)C24—C19—C17121.5 (2)
C9—C8—H8A110.7C20—C19—C17120.6 (2)
C7—C8—H8A110.7C21—C20—C19120.9 (2)
C9—C8—H8B110.7C21—C20—H20119.6
C7—C8—H8B110.7C19—C20—H20119.6
H8A—C8—H8B108.8C22—C21—C20120.4 (3)
N1—C9—C8103.28 (19)C22—C21—H21119.8
N1—C9—H9A111.1C20—C21—H21119.8
C8—C9—H9A111.1C21—C22—C23119.9 (3)
N1—C9—H9B111.1C21—C22—H22120.0
C8—C9—H9B111.1C23—C22—H22120.0
H9A—C9—H9B109.1C22—C23—C24120.7 (3)
O6—C10—N1121.4 (2)C22—C23—H23119.6
O6—C10—C11124.9 (2)C24—C23—H23119.6
N1—C10—C11113.73 (18)C19—C24—C23120.1 (3)
C4—C11—C10121.9 (2)C19—C24—H24119.9
C4—C11—C1122.42 (19)C23—C24—H24119.9
C10—C11—C1115.64 (17)
C2—O1—C1—C1119.3 (3)C6—N1—C9—C89.5 (2)
C1—O1—C2—O2174.3 (2)C10—N1—C9—C8170.22 (18)
C1—O1—C2—C31.0 (3)C7—C8—C9—N123.0 (2)
C16—O3—C3—C468.2 (2)C6—N1—C10—O6178.39 (19)
C16—O3—C3—C258.3 (2)C9—N1—C10—O61.9 (3)
C16—O3—C3—C14173.30 (18)C6—N1—C10—C113.0 (3)
O2—C2—C3—O338.1 (3)C9—N1—C10—C11176.68 (18)
O1—C2—C3—O3146.7 (2)C5—C4—C11—C105.0 (3)
O2—C2—C3—C4163.4 (2)C3—C4—C11—C10171.69 (18)
O1—C2—C3—C421.4 (3)C5—C4—C11—C1175.1 (2)
O2—C2—C3—C1473.2 (3)C3—C4—C11—C18.2 (3)
O1—C2—C3—C14102.0 (2)O6—C10—C11—C4176.1 (2)
O3—C3—C4—C11150.41 (18)N1—C10—C11—C42.5 (3)
C2—C3—C4—C1125.7 (3)O6—C10—C11—C13.8 (3)
C14—C3—C4—C1196.2 (2)N1—C10—C11—C1177.63 (18)
O3—C3—C4—C532.9 (3)O1—C1—C11—C414.4 (3)
C2—C3—C4—C5157.67 (18)O1—C1—C11—C10165.72 (18)
C14—C3—C4—C580.4 (2)C7—O5—C12—C1331.7 (3)
C11—C4—C5—C62.0 (3)C7—O4—C13—C123.3 (3)
C3—C4—C5—C6174.58 (19)O5—C12—C13—O421.5 (3)
C4—C5—C6—N13.3 (3)O3—C3—C14—C15170.4 (2)
C4—C5—C6—C7174.3 (2)C4—C3—C14—C1570.9 (3)
C10—N1—C6—C56.0 (3)C2—C3—C14—C1554.0 (3)
C9—N1—C6—C5173.7 (2)C17—N2—C16—O74.6 (4)
C10—N1—C6—C7172.05 (18)C17—N2—C16—O3174.3 (2)
C9—N1—C6—C78.3 (2)C3—O3—C16—O710.1 (3)
C13—O4—C7—O516.4 (3)C3—O3—C16—N2170.89 (18)
C13—O4—C7—C6104.7 (2)C16—N2—C17—C19166.5 (2)
C13—O4—C7—C8137.5 (2)C16—N2—C17—C1868.9 (3)
C12—O5—C7—O430.5 (3)N2—C17—C19—C2499.6 (3)
C12—O5—C7—C692.8 (2)C18—C17—C19—C24136.5 (3)
C12—O5—C7—C8155.1 (2)N2—C17—C19—C2077.4 (3)
C5—C6—C7—O435.3 (3)C18—C17—C19—C2046.5 (3)
N1—C6—C7—O4146.85 (19)C24—C19—C20—C210.9 (4)
C5—C6—C7—O584.0 (3)C17—C19—C20—C21177.9 (2)
N1—C6—C7—O593.8 (2)C19—C20—C21—C221.3 (4)
C5—C6—C7—C8159.9 (2)C20—C21—C22—C230.8 (4)
N1—C6—C7—C822.3 (2)C21—C22—C23—C240.0 (5)
O4—C7—C8—C9151.2 (2)C20—C19—C24—C230.0 (4)
O5—C7—C8—C989.0 (2)C17—C19—C24—C23177.1 (3)
C6—C7—C8—C927.6 (2)C22—C23—C24—C190.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O6i0.882.112.988 (2)173
Symmetry code: (i) x, y, z1.

Experimental details

Crystal data
Chemical formulaC24H26N2O7
Mr454.47
Crystal system, space groupMonoclinic, P21
Temperature (K)296
a, b, c (Å)7.3998 (10), 16.383 (2), 9.2162 (13)
β (°) 92.322 (2)
V3)1116.4 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerBruker SMART APEX II CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.971, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
7148, 2612, 2352
Rint0.023
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.087, 1.06
No. of reflections2612
No. of parameters302
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.13
Absolute structureFriedel pairs merged as equivalent data

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O6i0.882.112.988 (2)172.5
Symmetry code: (i) x, y, z1.
 

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