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In the crystal structure of the title compound, C31H25NO4, the five-membered heterocyclic ring is in an envelope conformation and the dihydro­pyrone ring is in a half-chair conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051264/nc2063sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051264/nc2063Isup2.hkl
Contains datablock I

CCDC reference: 667423

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.055
  • wR factor = 0.160
  • Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 400 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.86 Ratio PLAT411_ALERT_2_C Short Inter H...H Contact H3 .. H3 .. 2.12 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C1 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C2 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C3 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 4 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Spiroheterocycles belong to an important class of compounds with highly pronounced biological activities·(James et al. 1991) The central skeleton of many natural products and pharmacologically active compounds contain highly substituted pyrrolidines which are of much prominence (Deshong et al., 1983). Some of the biological active compounds such as rhyncophylline, corynoxeine,nitraphylline,vincatine, horsifiline,etc (Henrickson et al. 1962) contain pyrrolidine and oxindole moiety which forms a separate class of alkaloids (Fujimori 1990). In view of this we have determined the structure of the title compound.

The chromanone moiety consists of a methoxy benzene ring fused with a five membered heterocyclic ring which adopts a sofa conformation. The dihydropyrone ring is in an half chair conformation. The nitrogen atom of the pyrrolidine ring is slightly pyramidal, the sum of the angles amount to 342.04 °.

Related literature top

For related literature, see: Fujimori (1990), James et al. (1991), Deshong et al. (1983) and Henrickson et al. (1962).

Experimental top

A mixture of acenapthenequinone (acenaphthylene-1,2-dione) (1 mmol, 0.102 g), sarcosine (2-methylaminoacetic acid)(1 mmol, 0.046 g) and the dipolarophile (3-arylidene-4-chromanone) (1 mmol, 0.2 g) in aqueous methanol (20 ml) was refluxed for 4 h and the reaction was subsequently monitored by TLC for the disappearance of the starting materials. The solvent was removed under reduced pressure and the crude product was purified by column chromatography using silica gel and petroleum ether-ethyl acetate (9:1) as eluent to give the cycloadduct.

Refinement top

All H atoms were positioned with idealized geometry and were refined isotropic with Uiso(H) = 1.5 Ueq(C) for methyl H atoms and 1.2 Ueq(C) for all other H atoms using a riding model with C—H = 0.93 - 0.98 Å.

Structure description top

Spiroheterocycles belong to an important class of compounds with highly pronounced biological activities·(James et al. 1991) The central skeleton of many natural products and pharmacologically active compounds contain highly substituted pyrrolidines which are of much prominence (Deshong et al., 1983). Some of the biological active compounds such as rhyncophylline, corynoxeine,nitraphylline,vincatine, horsifiline,etc (Henrickson et al. 1962) contain pyrrolidine and oxindole moiety which forms a separate class of alkaloids (Fujimori 1990). In view of this we have determined the structure of the title compound.

The chromanone moiety consists of a methoxy benzene ring fused with a five membered heterocyclic ring which adopts a sofa conformation. The dihydropyrone ring is in an half chair conformation. The nitrogen atom of the pyrrolidine ring is slightly pyramidal, the sum of the angles amount to 342.04 °.

For related literature, see: Fujimori (1990), James et al. (1991), Deshong et al. (1983) and Henrickson et al. (1962).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. ORTEP representation of the molecule showing the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability.
6''-Methoxy-1'-methyl-4'-phenylacenaphthene-1-spiro-2'-pyrrolidine-3'- spiro-3''-chroman-2,4''-dione top
Crystal data top
C31H25NO4Z = 2
Mr = 475.52F(000) = 500
Triclinic, P1Dx = 1.314 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3233 (6) ÅCell parameters from 6077 reflections
b = 9.2393 (7) Åθ = 2.5–27.7°
c = 15.9107 (12) ŵ = 0.09 mm1
α = 79.969 (4)°T = 297 K
β = 88.820 (4)°Cubic, colourless
γ = 86.311 (4)°0.25 × 0.22 × 0.20 mm
V = 1202.30 (16) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
5771 independent reflections
Radiation source: fine-focus sealed tube3881 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
φ and ω scansθmax = 28.4°, θmin = 1.3°
Absorption correction: multi-scan
(Blessing, 1995)
h = 1011
Tmin = 0.969, Tmax = 0.983k = 912
14955 measured reflectionsl = 2020
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0754P)2 + 0.2718P]
where P = (Fo2 + 2Fc2)/3
5771 reflections(Δ/σ)max < 0.001
327 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C31H25NO4γ = 86.311 (4)°
Mr = 475.52V = 1202.30 (16) Å3
Triclinic, P1Z = 2
a = 8.3233 (6) ÅMo Kα radiation
b = 9.2393 (7) ŵ = 0.09 mm1
c = 15.9107 (12) ÅT = 297 K
α = 79.969 (4)°0.25 × 0.22 × 0.20 mm
β = 88.820 (4)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
5771 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
3881 reflections with I > 2σ(I)
Tmin = 0.969, Tmax = 0.983Rint = 0.038
14955 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.160H-atom parameters constrained
S = 1.03Δρmax = 0.28 e Å3
5771 reflectionsΔρmin = 0.28 e Å3
327 parameters
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
C10.57850 (18)0.03937 (18)0.27098 (11)0.0360 (4)
C20.40922 (18)0.00749 (17)0.31375 (10)0.0346 (3)
C30.45746 (19)0.09347 (19)0.40289 (11)0.0408 (4)
H30.46110.02000.44030.049*
C40.6312 (2)0.1479 (2)0.38993 (12)0.0462 (4)
H4A0.68730.17490.44380.055*
H4B0.63760.23120.36010.055*
C50.61230 (19)0.0249 (2)0.18623 (12)0.0421 (4)
C60.6259 (2)0.0998 (2)0.11601 (11)0.0432 (4)
C70.6504 (2)0.1087 (3)0.02958 (13)0.0577 (5)
H70.65680.02440.00480.069*
C80.6655 (3)0.2480 (3)0.02011 (14)0.0674 (6)
H80.67920.25550.07880.081*
C90.6607 (3)0.3738 (3)0.01491 (14)0.0644 (6)
H90.67430.46390.02010.077*
C100.6304 (2)0.4866 (2)0.14943 (14)0.0565 (5)
H100.64010.58230.12050.068*
C110.6114 (2)0.4608 (2)0.23585 (15)0.0557 (5)
H110.61000.54000.26480.067*
C120.5937 (2)0.31861 (19)0.28313 (12)0.0444 (4)
H120.58270.30430.34220.053*
C130.59326 (18)0.20230 (18)0.24059 (11)0.0364 (4)
C140.61716 (19)0.22864 (19)0.15170 (11)0.0395 (4)
C150.6353 (2)0.3685 (2)0.10360 (12)0.0484 (4)
C160.3152 (2)0.10079 (18)0.26368 (11)0.0407 (4)
H16A0.37830.19180.26060.049*
H16B0.21610.12600.29420.049*
C170.30017 (18)0.13009 (18)0.31895 (11)0.0363 (4)
C180.1461 (2)0.33730 (19)0.22831 (12)0.0427 (4)
H180.14760.39090.27260.051*
C190.0768 (2)0.3996 (2)0.15207 (13)0.0484 (4)
C200.0703 (2)0.3165 (2)0.08699 (13)0.0558 (5)
H200.02140.35830.03570.067*
C210.1346 (2)0.1749 (2)0.09756 (13)0.0518 (5)
H210.12810.12030.05400.062*
C220.20975 (19)0.11263 (19)0.17369 (11)0.0396 (4)
C230.21491 (18)0.19285 (18)0.23951 (11)0.0369 (4)
C240.0114 (3)0.6291 (3)0.19620 (18)0.0801 (7)
H24A0.05180.58530.24400.120*
H24B0.03460.72580.17410.120*
H24C0.11960.63600.21430.120*
C250.3443 (2)0.2068 (2)0.44581 (12)0.0490 (5)
C260.3616 (3)0.3527 (3)0.43840 (17)0.0727 (7)
H260.44230.38460.40340.087*
C270.2594 (4)0.4537 (3)0.4829 (2)0.0962 (10)
H270.27170.55230.47720.115*
C280.1417 (4)0.4081 (4)0.53457 (19)0.0990 (11)
H280.07590.47610.56580.119*
C290.1200 (3)0.2623 (4)0.54074 (17)0.0932 (10)
H290.03720.23090.57470.112*
C300.2205 (3)0.1618 (3)0.49687 (14)0.0681 (6)
H300.20510.06290.50150.082*
C310.8618 (2)0.0306 (3)0.31296 (15)0.0604 (6)
H31A0.92780.05290.36290.091*
H31B0.89010.06120.27950.091*
H31C0.87870.10750.27970.091*
N10.69349 (16)0.01929 (16)0.33844 (10)0.0426 (4)
O10.63514 (17)0.15490 (15)0.18358 (10)0.0584 (4)
O20.27733 (15)0.02802 (13)0.17924 (8)0.0454 (3)
O30.28659 (16)0.18571 (15)0.38289 (8)0.0512 (3)
O40.01298 (19)0.54128 (16)0.13208 (10)0.0658 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0284 (7)0.0367 (9)0.0444 (9)0.0016 (6)0.0011 (6)0.0117 (7)
C20.0284 (7)0.0340 (8)0.0416 (9)0.0021 (6)0.0004 (6)0.0074 (7)
C30.0328 (8)0.0427 (10)0.0457 (10)0.0018 (7)0.0032 (7)0.0041 (7)
C40.0353 (9)0.0444 (10)0.0573 (11)0.0005 (7)0.0079 (8)0.0041 (8)
C50.0293 (8)0.0431 (10)0.0576 (11)0.0022 (7)0.0030 (7)0.0198 (8)
C60.0320 (8)0.0520 (11)0.0485 (10)0.0047 (7)0.0056 (7)0.0173 (8)
C70.0466 (11)0.0790 (15)0.0534 (12)0.0086 (10)0.0081 (9)0.0276 (11)
C80.0612 (13)0.0972 (19)0.0441 (12)0.0118 (12)0.0066 (9)0.0112 (12)
C90.0566 (13)0.0773 (16)0.0537 (13)0.0105 (11)0.0020 (10)0.0064 (11)
C100.0549 (12)0.0399 (11)0.0723 (15)0.0078 (8)0.0025 (10)0.0015 (10)
C110.0568 (12)0.0395 (11)0.0752 (15)0.0086 (8)0.0005 (10)0.0200 (10)
C120.0405 (9)0.0460 (10)0.0507 (11)0.0061 (7)0.0012 (8)0.0184 (8)
C130.0285 (8)0.0377 (9)0.0445 (9)0.0022 (6)0.0004 (6)0.0117 (7)
C140.0289 (8)0.0445 (10)0.0464 (10)0.0025 (6)0.0010 (7)0.0113 (8)
C150.0395 (9)0.0508 (11)0.0526 (11)0.0061 (8)0.0004 (8)0.0019 (9)
C160.0323 (8)0.0385 (9)0.0519 (10)0.0024 (6)0.0034 (7)0.0089 (8)
C170.0272 (7)0.0407 (9)0.0418 (9)0.0019 (6)0.0031 (6)0.0095 (7)
C180.0348 (9)0.0434 (10)0.0498 (10)0.0026 (7)0.0026 (7)0.0102 (8)
C190.0381 (9)0.0463 (11)0.0575 (12)0.0059 (7)0.0003 (8)0.0032 (9)
C200.0514 (11)0.0614 (13)0.0509 (11)0.0085 (9)0.0113 (9)0.0028 (10)
C210.0497 (11)0.0592 (12)0.0479 (11)0.0053 (9)0.0107 (8)0.0147 (9)
C220.0301 (8)0.0424 (10)0.0469 (10)0.0002 (7)0.0018 (7)0.0096 (8)
C230.0263 (7)0.0419 (9)0.0425 (9)0.0008 (6)0.0009 (6)0.0083 (7)
C240.0880 (18)0.0550 (14)0.0968 (19)0.0202 (12)0.0077 (14)0.0201 (13)
C250.0379 (9)0.0572 (12)0.0482 (11)0.0075 (8)0.0071 (8)0.0040 (9)
C260.0552 (13)0.0555 (14)0.1002 (19)0.0099 (10)0.0027 (12)0.0087 (12)
C270.0789 (19)0.0747 (18)0.123 (3)0.0311 (14)0.0210 (18)0.0269 (17)
C280.079 (2)0.135 (3)0.0760 (18)0.064 (2)0.0102 (15)0.0235 (18)
C290.0667 (16)0.154 (3)0.0644 (16)0.0524 (18)0.0146 (12)0.0203 (17)
C300.0509 (12)0.0996 (18)0.0568 (13)0.0224 (11)0.0060 (10)0.0164 (12)
C310.0271 (9)0.0734 (14)0.0803 (15)0.0004 (8)0.0001 (9)0.0134 (11)
N10.0266 (7)0.0465 (9)0.0537 (9)0.0015 (6)0.0034 (6)0.0054 (7)
O10.0538 (8)0.0449 (8)0.0815 (10)0.0008 (6)0.0071 (7)0.0273 (7)
O20.0452 (7)0.0445 (7)0.0488 (7)0.0040 (5)0.0088 (5)0.0155 (6)
O30.0511 (8)0.0594 (8)0.0442 (7)0.0100 (6)0.0001 (6)0.0173 (6)
O40.0684 (10)0.0510 (9)0.0729 (10)0.0179 (7)0.0084 (7)0.0033 (7)
Geometric parameters (Å, º) top
C1—N11.461 (2)C16—H16B0.9700
C1—C131.511 (2)C17—O31.2173 (19)
C1—C51.579 (2)C17—C231.472 (2)
C1—C21.604 (2)C18—C191.371 (3)
C2—C171.527 (2)C18—C231.401 (2)
C2—C161.530 (2)C18—H180.9300
C2—C31.547 (2)C19—O41.367 (2)
C3—C251.517 (2)C19—C201.396 (3)
C3—C41.522 (2)C20—C211.365 (3)
C3—H30.9800C20—H200.9300
C4—N11.440 (2)C21—C221.390 (2)
C4—H4A0.9700C21—H210.9300
C4—H4B0.9700C22—O21.371 (2)
C5—O11.212 (2)C22—C231.387 (2)
C5—C61.467 (3)C24—O41.409 (3)
C6—C71.375 (3)C24—H24A0.9600
C6—C141.403 (2)C24—H24B0.9600
C7—C81.400 (3)C24—H24C0.9600
C7—H70.9300C25—C261.372 (3)
C8—C91.372 (3)C25—C301.387 (3)
C8—H80.9300C26—C271.394 (3)
C9—C151.415 (3)C26—H260.9300
C9—H90.9300C27—C281.359 (5)
C10—C111.362 (3)C27—H270.9300
C10—C151.412 (3)C28—C291.368 (5)
C10—H100.9300C28—H280.9300
C11—C121.410 (3)C29—C301.378 (3)
C11—H110.9300C29—H290.9300
C12—C131.366 (2)C30—H300.9300
C12—H120.9300C31—N11.453 (2)
C13—C141.405 (2)C31—H31A0.9600
C14—C151.398 (3)C31—H31B0.9600
C16—O21.426 (2)C31—H31C0.9600
C16—H16A0.9700
N1—C1—C13111.49 (13)O2—C16—H16B109.0
N1—C1—C5113.14 (13)C2—C16—H16B109.0
C13—C1—C5101.98 (13)H16A—C16—H16B107.8
N1—C1—C2102.92 (13)O3—C17—C23122.31 (15)
C13—C1—C2116.02 (13)O3—C17—C2123.07 (15)
C5—C1—C2111.71 (12)C23—C17—C2114.61 (14)
C17—C2—C16105.91 (13)C19—C18—C23120.01 (17)
C17—C2—C3112.42 (13)C19—C18—H18120.0
C16—C2—C3111.65 (13)C23—C18—H18120.0
C17—C2—C1109.67 (13)O4—C19—C18125.42 (18)
C16—C2—C1114.13 (13)O4—C19—C20115.01 (17)
C3—C2—C1103.22 (12)C18—C19—C20119.56 (17)
C25—C3—C4116.79 (15)C21—C20—C19121.00 (18)
C25—C3—C2117.08 (14)C21—C20—H20119.5
C4—C3—C2103.40 (13)C19—C20—H20119.5
C25—C3—H3106.2C20—C21—C22119.74 (18)
C4—C3—H3106.2C20—C21—H21120.1
C2—C3—H3106.2C22—C21—H21120.1
N1—C4—C3100.96 (13)O2—C22—C23123.02 (15)
N1—C4—H4A111.6O2—C22—C21117.01 (16)
C3—C4—H4A111.6C23—C22—C21119.97 (16)
N1—C4—H4B111.6C22—C23—C18119.67 (15)
C3—C4—H4B111.6C22—C23—C17120.31 (15)
H4A—C4—H4B109.4C18—C23—C17119.93 (15)
O1—C5—C6127.80 (17)O4—C24—H24A109.5
O1—C5—C1124.22 (17)O4—C24—H24B109.5
C6—C5—C1107.73 (14)H24A—C24—H24B109.5
C7—C6—C14119.71 (18)O4—C24—H24C109.5
C7—C6—C5132.76 (17)H24A—C24—H24C109.5
C14—C6—C5107.47 (15)H24B—C24—H24C109.5
C6—C7—C8118.2 (2)C26—C25—C30118.4 (2)
C6—C7—H7120.9C26—C25—C3123.00 (19)
C8—C7—H7120.9C30—C25—C3118.56 (19)
C9—C8—C7122.2 (2)C25—C26—C27120.6 (3)
C9—C8—H8118.9C25—C26—H26119.7
C7—C8—H8118.9C27—C26—H26119.7
C8—C9—C15121.0 (2)C28—C27—C26120.0 (3)
C8—C9—H9119.5C28—C27—H27120.0
C15—C9—H9119.5C26—C27—H27120.0
C11—C10—C15120.14 (18)C27—C28—C29120.0 (2)
C11—C10—H10119.9C27—C28—H28120.0
C15—C10—H10119.9C29—C28—H28120.0
C10—C11—C12122.58 (18)C28—C29—C30120.3 (3)
C10—C11—H11118.7C28—C29—H29119.9
C12—C11—H11118.7C30—C29—H29119.9
C13—C12—C11118.85 (18)C29—C30—C25120.6 (3)
C13—C12—H12120.6C29—C30—H30119.7
C11—C12—H12120.6C25—C30—H30119.7
C12—C13—C14118.45 (16)N1—C31—H31A109.5
C12—C13—C1132.26 (16)N1—C31—H31B109.5
C14—C13—C1109.23 (14)H31A—C31—H31B109.5
C15—C14—C6123.07 (17)N1—C31—H31C109.5
C15—C14—C13123.62 (16)H31A—C31—H31C109.5
C6—C14—C13113.28 (16)H31B—C31—H31C109.5
C14—C15—C10116.31 (17)C4—N1—C31116.72 (15)
C14—C15—C9115.80 (19)C4—N1—C1108.78 (13)
C10—C15—C9127.87 (19)C31—N1—C1116.55 (15)
O2—C16—C2113.12 (14)C22—O2—C16114.83 (13)
O2—C16—H16A109.0C19—O4—C24117.59 (17)
C2—C16—H16A109.0
N1—C1—C2—C17118.59 (14)C11—C10—C15—C9177.2 (2)
C13—C1—C2—C173.43 (19)C8—C9—C15—C140.5 (3)
C5—C1—C2—C17119.72 (15)C8—C9—C15—C10178.6 (2)
N1—C1—C2—C16122.79 (14)C17—C2—C16—O260.91 (17)
C13—C1—C2—C16115.19 (15)C3—C2—C16—O2176.41 (13)
C5—C1—C2—C161.10 (19)C1—C2—C16—O259.83 (18)
N1—C1—C2—C31.42 (15)C16—C2—C17—O3139.69 (16)
C13—C1—C2—C3123.44 (15)C3—C2—C17—O317.5 (2)
C5—C1—C2—C3120.27 (14)C1—C2—C17—O396.72 (18)
C17—C2—C3—C2587.35 (18)C16—C2—C17—C2341.67 (18)
C16—C2—C3—C2531.5 (2)C3—C2—C17—C23163.86 (13)
C1—C2—C3—C25154.56 (15)C1—C2—C17—C2381.92 (16)
C17—C2—C3—C4142.70 (14)C23—C18—C19—O4176.67 (17)
C16—C2—C3—C498.42 (15)C23—C18—C19—C202.2 (3)
C1—C2—C3—C424.60 (16)O4—C19—C20—C21177.81 (19)
C25—C3—C4—N1172.33 (15)C18—C19—C20—C211.2 (3)
C2—C3—C4—N142.21 (17)C19—C20—C21—C220.9 (3)
N1—C1—C5—O149.1 (2)C20—C21—C22—O2177.58 (17)
C13—C1—C5—O1168.97 (16)C20—C21—C22—C231.9 (3)
C2—C1—C5—O166.5 (2)O2—C22—C23—C18178.58 (15)
N1—C1—C5—C6125.49 (15)C21—C22—C23—C180.9 (2)
C13—C1—C5—C65.63 (16)O2—C22—C23—C172.1 (2)
C2—C1—C5—C6118.92 (14)C21—C22—C23—C17177.41 (16)
O1—C5—C6—C77.5 (3)C19—C18—C23—C221.2 (3)
C1—C5—C6—C7178.13 (18)C19—C18—C23—C17175.33 (15)
O1—C5—C6—C14169.53 (17)O3—C17—C23—C22168.08 (16)
C1—C5—C6—C144.81 (17)C2—C17—C23—C2213.3 (2)
C14—C6—C7—C80.1 (3)O3—C17—C23—C1815.4 (2)
C5—C6—C7—C8176.89 (19)C2—C17—C23—C18163.22 (14)
C6—C7—C8—C91.7 (3)C4—C3—C25—C2630.5 (3)
C7—C8—C9—C151.9 (3)C2—C3—C25—C2692.9 (2)
C15—C10—C11—C120.9 (3)C4—C3—C25—C30147.63 (19)
C10—C11—C12—C131.0 (3)C2—C3—C25—C3089.0 (2)
C11—C12—C13—C142.6 (2)C30—C25—C26—C271.6 (3)
C11—C12—C13—C1179.43 (16)C3—C25—C26—C27176.5 (2)
N1—C1—C13—C1251.5 (2)C25—C26—C27—C280.3 (4)
C5—C1—C13—C12172.49 (17)C26—C27—C28—C292.2 (4)
C2—C1—C13—C1265.9 (2)C27—C28—C29—C302.1 (4)
N1—C1—C13—C14125.54 (14)C28—C29—C30—C250.2 (4)
C5—C1—C13—C144.52 (16)C26—C25—C30—C291.6 (3)
C2—C1—C13—C14117.10 (15)C3—C25—C30—C29176.5 (2)
C7—C6—C14—C151.3 (3)C3—C4—N1—C31179.88 (16)
C5—C6—C14—C15176.24 (15)C3—C4—N1—C145.72 (17)
C7—C6—C14—C13179.48 (16)C13—C1—N1—C4154.45 (14)
C5—C6—C14—C131.97 (19)C5—C1—N1—C491.30 (16)
C12—C13—C14—C152.6 (2)C2—C1—N1—C429.42 (17)
C1—C13—C14—C15179.92 (15)C13—C1—N1—C3171.06 (19)
C12—C13—C14—C6175.61 (15)C5—C1—N1—C3143.2 (2)
C1—C13—C14—C61.88 (19)C2—C1—N1—C31163.90 (15)
C6—C14—C15—C10177.29 (16)C23—C22—O2—C1616.0 (2)
C13—C14—C15—C100.7 (3)C21—C22—O2—C16164.50 (15)
C6—C14—C15—C91.1 (3)C2—C16—O2—C2249.12 (18)
C13—C14—C15—C9179.11 (16)C18—C19—O4—C243.1 (3)
C11—C10—C15—C141.0 (3)C20—C19—O4—C24178.0 (2)

Experimental details

Crystal data
Chemical formulaC31H25NO4
Mr475.52
Crystal system, space groupTriclinic, P1
Temperature (K)297
a, b, c (Å)8.3233 (6), 9.2393 (7), 15.9107 (12)
α, β, γ (°)79.969 (4), 88.820 (4), 86.311 (4)
V3)1202.30 (16)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.25 × 0.22 × 0.20
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.969, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
14955, 5771, 3881
Rint0.038
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.160, 1.03
No. of reflections5771
No. of parameters327
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.28

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).

 

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