Literature DB >> 21582278

4-(9-Anthr-yl)-1-(2-methoxy-phen-yl)spiro-[azetidin-3,9'-xanthen]-2-one.

Serife Pınar Yalçın, Mehmet Akkurt, Aliasghar Jarrahpour, Edris Ebrahimi, Orhan Büyükgüngör.   

Abstract

The stabilized conformation of the title compound, C(36)H(25)NO(3), 4-(9-anthryl)-1-(2-methoxyphenyl)-spiro[azetid-in-3,9'-xanthen]-2-one, may be compared with that of the isomeric compound 4-(9-anthr-yl)-1-(4-methoxy-phen-yl)spiro-[azetidin-3,9'-xanthen]-2-one. In the title isomer, the meth-oxy group is slightly twisted out of the plane of the attached benzene ring, with a C-O-C-C torsion angle of 31.5 (2)°. Its β-lactam ring is essentially planar, with a maximum deviation of -0.021 (1) Å. The β-lactam ring makes dihedral angles of 18.815 (9), 83.33 (7) and 53.62 (8)° with the mean planes of the benzene, xanthene and anthracene ring systems, respectively. The structure is stabilized by C-H⋯π, C-H⋯N and C-H⋯O inter-actions.

Entities:  

Year:  2009        PMID： 21582278      PMCID： PMC2968572          DOI： 10.1107/S1600536809005200

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background to β-lactam anti­biotics, see: Banik et al. (2004 ▶); Georg & Ravikumar (1993 ▶); Jarrahpour & Khalili (2007 ▶); Palomo et al. (2001 ▶). For the crystal structure of the isomeric compound 4-(9-anthr­yl)-1-(4-methoxy­phen­yl)spiro­[azetidin-3,9′-xanthen]-2-one, see: Akkurt, Karaca et al. (2008 ▶). For the crystal structures of related compounds, see: Pınar et al. (2006 ▶); Akkurt, Jarrahpour et al. (2008 ▶). For ring-puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C36H25NO3 M = 519.57 Monoclinic, a = 11.8496 (3) Å b = 15.3168 (5) Å c = 14.9883 (4) Å β = 106.536 (2)° V = 2607.84 (13) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 295 K 0.62 × 0.59 × 0.56 mm

Data collection

Stoe IPDS-II diffractometer Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.950, T max = 0.955 32362 measured reflections 5399 independent reflections 4314 reflections with I > 2σ(I) R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.106 S = 1.04 5399 reflections 363 parameters H-atom parameters constrained Δρmax = 0.16 e Å−3 Δρmin = −0.16 e Å−3 Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005200/sj2572sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005200/sj2572Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C36H25NO3F(000) = 1088
Mr = 519.57Dx = 1.323 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 32362 reflections
a = 11.8496 (3) Åθ = 1.4–28.0°
b = 15.3168 (5) ŵ = 0.08 mm−1
c = 14.9883 (4) ÅT = 295 K
β = 106.536 (2)°Prism, colourless
V = 2607.84 (13) Å30.62 × 0.59 × 0.56 mm
Z = 4
STOE IPDS-II diffractometer5399 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus4314 reflections with I > 2σ(I)
plane graphiteRint = 0.054
Detector resolution: 6.67 pixels mm-1θmax = 26.5°, θmin = 1.8°
ω scansh = −14→14
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −19→19
Tmin = 0.950, Tmax = 0.955l = −18→18
32362 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.106w = 1/[σ2(Fo2) + (0.048P)2 + 0.3336P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
5399 reflectionsΔρmax = 0.16 e Å−3
363 parametersΔρmin = −0.16 e Å−3
0 restraintsExtinction correction: SHELXL, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0105 (9)
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su'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.
xyzUiso*/Ueq
O1−0.01289 (9)0.44378 (8)0.31404 (8)0.0697 (4)
O20.36695 (10)0.55177 (7)0.51655 (7)0.0653 (4)
O30.30250 (9)0.78834 (7)0.27655 (8)0.0675 (4)
N10.33576 (9)0.64088 (7)0.38357 (7)0.0461 (3)
C10.36306 (11)0.58740 (9)0.19255 (9)0.0462 (4)
C20.47171 (12)0.57344 (10)0.26356 (11)0.0569 (5)
C30.57582 (14)0.56915 (12)0.24285 (15)0.0751 (7)
C40.58118 (17)0.57587 (14)0.15052 (17)0.0884 (8)
C50.48186 (17)0.58388 (13)0.08111 (15)0.0792 (7)
C60.36987 (14)0.58871 (10)0.09806 (11)0.0568 (5)
C70.26796 (15)0.59596 (11)0.02468 (10)0.0626 (5)
C80.15810 (13)0.60135 (9)0.03888 (9)0.0531 (4)
C90.05274 (17)0.60473 (11)−0.03720 (10)0.0675 (6)
C10−0.05367 (16)0.60989 (11)−0.02326 (11)0.0705 (6)
C11−0.06362 (14)0.61307 (11)0.06781 (12)0.0647 (5)
C120.03379 (12)0.61083 (9)0.14315 (10)0.0520 (4)
C130.14958 (11)0.60449 (8)0.13233 (8)0.0446 (4)
C140.25263 (11)0.60084 (8)0.20881 (8)0.0415 (3)
C150.23391 (11)0.62055 (8)0.30239 (8)0.0418 (4)
C160.20143 (11)0.54586 (8)0.36502 (8)0.0438 (4)
C170.19653 (12)0.45304 (9)0.33143 (9)0.0481 (4)
C180.29543 (15)0.40863 (10)0.32265 (11)0.0604 (5)
C190.28781 (19)0.32418 (11)0.28933 (12)0.0751 (7)
C200.1806 (2)0.28190 (11)0.26398 (12)0.0779 (7)
C210.08265 (17)0.32332 (11)0.27326 (11)0.0706 (6)
C220.09090 (13)0.40801 (10)0.30662 (9)0.0554 (5)
C23−0.00679 (12)0.51767 (10)0.36724 (10)0.0543 (5)
C24−0.10730 (14)0.53833 (12)0.39252 (13)0.0696 (6)
C25−0.10924 (16)0.61064 (12)0.44524 (14)0.0754 (7)
C26−0.01121 (17)0.66294 (12)0.47321 (13)0.0725 (6)
C270.08836 (14)0.64221 (10)0.44783 (11)0.0588 (5)
C280.09329 (12)0.56874 (9)0.39433 (9)0.0475 (4)
C290.31556 (12)0.57514 (9)0.43826 (9)0.0478 (4)
C300.42510 (11)0.70525 (9)0.39776 (9)0.0469 (4)
C310.53095 (13)0.69324 (11)0.46667 (10)0.0595 (5)
C320.62199 (13)0.75191 (12)0.47606 (12)0.0676 (6)
C330.60857 (14)0.82195 (13)0.41712 (12)0.0692 (6)
C340.50341 (14)0.83551 (11)0.34932 (11)0.0625 (5)
C350.41095 (12)0.77789 (9)0.33996 (9)0.0509 (4)
C360.2984 (2)0.82970 (17)0.19185 (16)0.1126 (9)
H20.470800.567200.325100.0680*
H30.645000.561600.290600.0900*
H40.653600.574700.137800.1060*
H50.486100.586400.020100.0950*
H70.273800.59720−0.035900.0750*
H90.058400.60330−0.097800.0810*
H10−0.120900.61140−0.073800.0850*
H11−0.137800.616800.077000.0780*
H120.024600.613500.202700.0620*
H150.176100.667700.294700.0500*
H180.368200.436500.339600.0720*
H190.354900.295800.284000.0900*
H200.175200.225300.240600.0930*
H210.010500.294700.257200.0850*
H24−0.173500.502900.373500.0840*
H25−0.176700.624500.462200.0900*
H26−0.012200.712200.509200.0870*
H270.154100.678200.466900.0700*
H310.540400.645500.506500.0710*
H320.692500.743900.522400.0810*
H330.670700.860600.422800.0830*
H340.494800.883500.309900.0750*
H36A0.357900.805400.167100.1350*
H36B0.312200.891100.202300.1350*
H36C0.222300.820800.148400.1350*
U11U22U33U12U13U23
O10.0557 (6)0.0655 (7)0.0769 (8)−0.0070 (5)0.0011 (5)−0.0118 (6)
O20.0716 (7)0.0750 (7)0.0390 (5)−0.0004 (5)−0.0009 (5)0.0127 (5)
O30.0614 (6)0.0611 (6)0.0668 (7)−0.0036 (5)−0.0031 (5)0.0181 (5)
N10.0486 (6)0.0482 (6)0.0351 (5)−0.0030 (5)0.0014 (4)0.0024 (5)
C10.0472 (7)0.0424 (7)0.0483 (7)−0.0006 (5)0.0123 (6)−0.0015 (6)
C20.0488 (8)0.0543 (8)0.0643 (9)0.0050 (6)0.0106 (7)−0.0072 (7)
C30.0470 (8)0.0730 (11)0.1011 (14)0.0045 (7)0.0142 (9)−0.0145 (10)
C40.0643 (11)0.0941 (14)0.1214 (18)−0.0015 (10)0.0499 (12)−0.0093 (13)
C50.0783 (12)0.0893 (13)0.0844 (13)−0.0026 (10)0.0464 (10)−0.0024 (10)
C60.0645 (9)0.0543 (8)0.0581 (8)−0.0024 (7)0.0280 (7)0.0001 (7)
C70.0828 (11)0.0667 (10)0.0409 (7)0.0005 (8)0.0217 (7)0.0020 (7)
C80.0677 (9)0.0498 (7)0.0371 (7)0.0005 (6)0.0073 (6)0.0024 (6)
C90.0905 (12)0.0628 (9)0.0369 (7)0.0051 (8)−0.0019 (7)0.0024 (7)
C100.0688 (11)0.0703 (10)0.0527 (9)0.0068 (8)−0.0147 (8)0.0012 (8)
C110.0511 (8)0.0640 (10)0.0661 (10)0.0047 (7)−0.0039 (7)0.0028 (8)
C120.0486 (7)0.0551 (8)0.0467 (7)0.0010 (6)0.0044 (6)0.0021 (6)
C130.0502 (7)0.0416 (6)0.0372 (6)0.0000 (5)0.0047 (5)0.0018 (5)
C140.0448 (6)0.0403 (6)0.0363 (6)0.0001 (5)0.0068 (5)0.0029 (5)
C150.0424 (6)0.0437 (7)0.0350 (6)0.0007 (5)0.0039 (5)0.0011 (5)
C160.0488 (7)0.0452 (7)0.0349 (6)0.0010 (5)0.0080 (5)0.0035 (5)
C170.0617 (8)0.0447 (7)0.0355 (6)0.0024 (6)0.0101 (6)0.0052 (5)
C180.0751 (10)0.0520 (8)0.0581 (9)0.0089 (7)0.0254 (7)0.0086 (7)
C190.1100 (14)0.0555 (9)0.0693 (11)0.0218 (10)0.0410 (10)0.0092 (8)
C200.1310 (17)0.0479 (9)0.0537 (9)0.0050 (10)0.0247 (10)−0.0042 (7)
C210.0950 (12)0.0539 (9)0.0527 (9)−0.0102 (9)0.0044 (8)−0.0038 (7)
C220.0668 (9)0.0511 (8)0.0414 (7)−0.0004 (7)0.0042 (6)0.0011 (6)
C230.0528 (8)0.0527 (8)0.0530 (8)0.0018 (6)0.0078 (6)0.0082 (7)
C240.0490 (8)0.0744 (11)0.0828 (11)0.0058 (7)0.0144 (8)0.0221 (9)
C250.0716 (11)0.0748 (12)0.0890 (13)0.0240 (9)0.0378 (10)0.0247 (10)
C260.0927 (12)0.0606 (10)0.0748 (11)0.0173 (9)0.0411 (10)0.0069 (8)
C270.0733 (9)0.0505 (8)0.0576 (9)0.0016 (7)0.0269 (7)0.0007 (7)
C280.0545 (8)0.0471 (7)0.0412 (7)0.0013 (6)0.0141 (6)0.0063 (6)
C290.0527 (7)0.0509 (7)0.0366 (6)0.0032 (6)0.0077 (5)0.0025 (6)
C300.0470 (7)0.0505 (7)0.0401 (7)−0.0019 (6)0.0073 (5)−0.0051 (6)
C310.0560 (8)0.0654 (9)0.0476 (8)−0.0018 (7)−0.0004 (6)−0.0011 (7)
C320.0479 (8)0.0869 (12)0.0600 (9)−0.0063 (8)0.0025 (7)−0.0119 (9)
C330.0535 (8)0.0846 (12)0.0700 (10)−0.0185 (8)0.0185 (7)−0.0104 (9)
C340.0654 (9)0.0606 (9)0.0635 (9)−0.0097 (7)0.0218 (8)0.0011 (7)
C350.0507 (7)0.0529 (8)0.0466 (7)−0.0011 (6)0.0100 (6)−0.0024 (6)
C360.1148 (17)0.1056 (17)0.0883 (15)−0.0211 (13)−0.0180 (13)0.0514 (13)
O1—C221.3795 (19)C23—C281.382 (2)
O1—C231.3745 (19)C24—C251.365 (3)
O2—C291.2121 (17)C25—C261.375 (3)
O3—C351.3730 (18)C26—C271.376 (3)
O3—C361.407 (3)C27—C281.393 (2)
N1—C151.4826 (16)C30—C311.392 (2)
N1—C291.3619 (17)C30—C351.3906 (19)
N1—C301.4177 (17)C31—C321.380 (2)
C1—C21.434 (2)C32—C331.370 (3)
C1—C61.441 (2)C33—C341.381 (2)
C1—C141.4127 (19)C34—C351.383 (2)
C2—C31.357 (2)C2—H20.9300
C3—C41.407 (3)C3—H30.9300
C4—C51.336 (3)C4—H40.9300
C5—C61.422 (3)C5—H50.9300
C6—C71.387 (2)C7—H70.9300
C7—C81.380 (2)C9—H90.9300
C8—C91.432 (2)C10—H100.9300
C8—C131.4335 (18)C11—H110.9300
C9—C101.338 (3)C12—H120.9300
C10—C111.404 (2)C15—H150.9800
C11—C121.366 (2)C18—H180.9300
C12—C131.430 (2)C19—H190.9300
C13—C141.4183 (17)C20—H200.9300
C14—C151.5115 (17)C21—H210.9300
C15—C161.5949 (17)C24—H240.9300
C16—C171.5038 (18)C25—H250.9300
C16—C281.509 (2)C26—H260.9300
C16—C291.5460 (19)C27—H270.9300
C17—C181.393 (2)C31—H310.9300
C17—C221.384 (2)C32—H320.9300
C18—C191.380 (2)C33—H330.9300
C19—C201.380 (3)C34—H340.9300
C20—C211.364 (3)C36—H36A0.9600
C21—C221.384 (2)C36—H36B0.9600
C23—C241.385 (2)C36—H36C0.9600
O2···C313.140 (2)C27···H152.8000
O3···C152.7559 (16)C27···H36Cv3.0300
O3···N12.7331 (15)C28···H122.8400
O3···C143.0474 (16)C29···H272.6100
O2···H312.5500C29···H182.7600
O3···H152.4400C29···H312.7800
N1···O32.7331 (15)C29···H22.8400
N1···C22.9236 (19)C30···H22.5100
N1···C273.336 (2)C31···H22.8100
N1···H22.3200C33···H5v2.7800
N1···H272.8400C34···H36A2.8200
C1···C183.582 (2)C34···H36B2.8100
C1···C303.4600 (19)C34···H19ix3.0200
C2···N12.9236 (19)C34···H5v2.8900
C2···C183.546 (2)C36···H342.6200
C2···C303.010 (2)C36···H24x3.0600
C2···C313.451 (2)H2···N12.3200
C2···C353.479 (2)H2···C152.8500
C5···C33i3.532 (3)H2···C292.8400
C8···C10ii3.448 (2)H2···C302.5100
C9···C11ii3.375 (2)H2···C312.8100
C9···C10ii3.409 (2)H2···H182.3800
C10···C8ii3.448 (2)H3···C24xi2.9200
C10···C9ii3.409 (2)H3···H24xi2.3400
C10···C10ii3.596 (2)H5···H72.4200
C10···C26i3.518 (3)H5···C5vii3.0900
C11···C9ii3.375 (2)H5···C33i2.7800
C12···C163.4978 (19)H5···C34i2.8900
C14···O33.0474 (16)H7···H52.4200
C14···C363.567 (3)H7···H92.4600
C14···C353.5551 (18)H9···H72.4600
C14···C183.368 (2)H9···C21ii2.9100
C15···O32.7559 (16)H10···H33xii2.4900
C16···C123.4978 (19)H12···C152.5100
C18···C143.368 (2)H12···C162.9100
C18···C31iii3.597 (2)H12···C232.9800
C18···C23.546 (2)H12···C282.8400
C18···C13.582 (2)H12···H152.1000
C19···C32iii3.567 (2)H15···O32.4400
C23···C24iv3.572 (2)H15···C122.5700
C23···C25iv3.384 (2)H15···C272.8000
C24···C23iv3.572 (2)H15···H122.1000
C24···C28iv3.553 (2)H18···C22.8300
C25···C23iv3.384 (2)H18···C292.7600
C26···C10v3.518 (3)H18···H22.3800
C27···N13.336 (2)H18···H31iii2.5800
C28···C24iv3.553 (2)H19···C34vi3.0200
C30···C23.010 (2)H24···H3viii2.3400
C30···C13.4600 (19)H24···C36xiii3.0600
C31···C23.451 (2)H24···H36Bxiii2.4200
C31···C18iii3.597 (2)H26···C9v3.0400
C31···O23.140 (2)H26···C10v2.7900
C32···C19iii3.567 (2)H26···C11v2.9300
C33···C5v3.532 (3)H27···N12.8400
C35···C143.5551 (18)H27···C153.0100
C35···C23.479 (2)H27···C292.6100
C36···C143.567 (3)H31···O22.5500
C2···H182.8300H31···C292.7800
C3···H34vi3.0100H31···C18iii2.8600
C3···H36Bvi3.0400H31···H18iii2.5800
C5···H5vii3.0900H32···C19iii2.9500
C9···H26i3.0400H33···H10xiv2.4900
C10···H26i2.7900H34···C362.6200
C11···H26i2.9300H34···H36A2.5800
C12···H152.5700H34···H36B2.3000
C15···H273.0100H34···C3ix3.0100
C15···H22.8500H36A···C342.8200
C15···H122.5100H36A···H342.5800
C16···H122.9100H36B···C342.8100
C18···H31iii2.8600H36B···H342.3000
C19···H32iii2.9500H36B···C3ix3.0400
C21···H9ii2.9100H36B···H24x2.4200
C23···H122.9800H36C···C27i3.0300
C24···H3viii2.9200
C22—O1—C23118.22 (12)N1—C30—C31119.75 (12)
C35—O3—C36117.53 (14)N1—C30—C35120.70 (12)
C15—N1—C2995.58 (10)C31—C30—C35119.44 (13)
C15—N1—C30131.90 (10)C30—C31—C32120.19 (15)
C29—N1—C30132.50 (11)C31—C32—C33120.02 (16)
C2—C1—C6116.22 (13)C32—C33—C34120.47 (17)
C2—C1—C14125.01 (12)C33—C34—C35120.11 (15)
C6—C1—C14118.76 (12)O3—C35—C30116.59 (12)
C1—C2—C3121.35 (15)O3—C35—C34123.67 (13)
C2—C3—C4121.33 (18)C30—C35—C34119.73 (13)
C3—C4—C5119.8 (2)C1—C2—H2119.00
C4—C5—C6121.7 (2)C3—C2—H2119.00
C1—C6—C5119.39 (15)C2—C3—H3119.00
C1—C6—C7120.04 (15)C4—C3—H3119.00
C5—C6—C7120.56 (16)C3—C4—H4120.00
C6—C7—C8121.94 (14)C5—C4—H4120.00
C7—C8—C9121.75 (13)C4—C5—H5119.00
C7—C8—C13118.98 (13)C6—C5—H5119.00
C9—C8—C13119.27 (14)C6—C7—H7119.00
C8—C9—C10121.64 (14)C8—C7—H7119.00
C9—C10—C11119.84 (16)C8—C9—H9119.00
C10—C11—C12121.18 (16)C10—C9—H9119.00
C11—C12—C13121.34 (13)C9—C10—H10120.00
C8—C13—C12116.73 (12)C11—C10—H10120.00
C8—C13—C14120.30 (12)C10—C11—H11119.00
C12—C13—C14122.97 (11)C12—C11—H11119.00
C1—C14—C13119.54 (11)C11—C12—H12119.00
C1—C14—C15125.24 (11)C13—C12—H12119.00
C13—C14—C15114.97 (11)N1—C15—H15109.00
N1—C15—C14120.22 (11)C14—C15—H15109.00
N1—C15—C1686.79 (8)C16—C15—H15109.00
C14—C15—C16121.78 (10)C17—C18—H18119.00
C15—C16—C17118.29 (10)C19—C18—H18119.00
C15—C16—C28111.83 (10)C18—C19—H19120.00
C15—C16—C2984.32 (9)C20—C19—H19120.00
C17—C16—C28111.21 (11)C19—C20—H20120.00
C17—C16—C29117.04 (11)C21—C20—H20120.00
C28—C16—C29111.69 (10)C20—C21—H21120.00
C16—C17—C18122.67 (13)C22—C21—H21120.00
C16—C17—C22120.45 (13)C23—C24—H24120.00
C18—C17—C22116.87 (13)C25—C24—H24120.00
C17—C18—C19121.44 (17)C24—C25—H25120.00
C18—C19—C20119.99 (19)C26—C25—H25120.00
C19—C20—C21119.81 (16)C25—C26—H26120.00
C20—C21—C22119.88 (17)C27—C26—H26120.00
O1—C22—C17122.63 (13)C26—C27—H27119.00
O1—C22—C21115.38 (15)C28—C27—H27119.00
C17—C22—C21121.99 (15)C30—C31—H31120.00
O1—C23—C24116.07 (14)C32—C31—H31120.00
O1—C23—C28122.39 (13)C31—C32—H32120.00
C24—C23—C28121.54 (14)C33—C32—H32120.00
C23—C24—C25120.09 (17)C32—C33—H33120.00
C24—C25—C26119.84 (18)C34—C33—H33120.00
C25—C26—C27119.86 (17)C33—C34—H34120.00
C26—C27—C28121.70 (15)C35—C34—H34120.00
C16—C28—C23120.78 (12)O3—C36—H36A109.00
C16—C28—C27122.24 (13)O3—C36—H36B109.00
C23—C28—C27116.97 (14)O3—C36—H36C109.00
O2—C29—N1132.46 (13)H36A—C36—H36B109.00
O2—C29—C16134.32 (13)H36A—C36—H36C110.00
N1—C29—C1693.16 (10)H36B—C36—H36C109.00
C23—O1—C22—C21164.09 (13)N1—C15—C16—C28108.45 (11)
C22—O1—C23—C24−163.94 (14)C14—C15—C16—C173.56 (18)
C22—O1—C23—C2816.0 (2)N1—C15—C16—C29−2.66 (9)
C23—O1—C22—C17−15.4 (2)C14—C15—C16—C28−127.61 (12)
C36—O3—C35—C3431.5 (2)C14—C15—C16—C29121.28 (12)
C36—O3—C35—C30−149.38 (16)C29—C16—C28—C2731.69 (17)
C29—N1—C30—C35−164.50 (14)C15—C16—C29—O2−179.64 (17)
C29—N1—C15—C163.02 (10)C15—C16—C28—C23117.93 (13)
C30—N1—C15—C1456.11 (18)C15—C16—C28—C27−60.86 (16)
C29—N1—C30—C3119.3 (2)C28—C16—C17—C2217.30 (16)
C30—N1—C15—C16−178.59 (13)C29—C16—C17—C18−33.39 (18)
C15—N1—C30—C3517.7 (2)C29—C16—C17—C22147.33 (13)
C15—N1—C29—C16−3.11 (10)C15—C16—C17—C1865.15 (17)
C30—N1—C29—C16178.51 (13)C17—C16—C28—C23−16.74 (17)
C29—N1—C15—C14−122.28 (12)C17—C16—C28—C27164.47 (13)
C15—N1—C29—O2179.35 (17)C29—C16—C28—C23−149.52 (13)
C15—N1—C30—C31−158.49 (13)C28—C16—C17—C18−163.42 (13)
C30—N1—C29—O21.0 (3)C15—C16—C17—C22−114.14 (14)
C2—C1—C14—C13−173.20 (13)C28—C16—C29—N1−108.37 (11)
C6—C1—C14—C15−166.21 (12)C17—C16—C29—O2−60.7 (2)
C14—C1—C6—C5173.86 (14)C17—C16—C29—N1121.83 (12)
C14—C1—C6—C7−5.2 (2)C15—C16—C29—N12.89 (10)
C2—C1—C6—C7175.67 (14)C28—C16—C29—O269.1 (2)
C2—C1—C6—C5−5.3 (2)C16—C17—C22—C21178.37 (13)
C6—C1—C14—C137.72 (19)C18—C17—C22—O1178.49 (13)
C14—C1—C2—C3−173.76 (15)C16—C17—C18—C19−178.29 (14)
C2—C1—C14—C1512.9 (2)C22—C17—C18—C191.0 (2)
C6—C1—C2—C35.3 (2)C16—C17—C22—O1−2.2 (2)
C1—C2—C3—C4−1.7 (3)C18—C17—C22—C21−1.0 (2)
C2—C3—C4—C5−2.2 (3)C17—C18—C19—C20−0.1 (3)
C3—C4—C5—C62.1 (3)C18—C19—C20—C21−1.0 (3)
C4—C5—C6—C11.8 (3)C19—C20—C21—C221.0 (2)
C4—C5—C6—C7−179.22 (18)C20—C21—C22—O1−179.54 (14)
C5—C6—C7—C8−179.57 (16)C20—C21—C22—C17−0.1 (2)
C1—C6—C7—C8−0.6 (2)O1—C23—C28—C160.9 (2)
C6—C7—C8—C133.6 (2)C24—C23—C28—C16−179.17 (14)
C6—C7—C8—C9−177.04 (15)C24—C23—C28—C27−0.3 (2)
C7—C8—C13—C14−0.9 (2)C28—C23—C24—C250.1 (3)
C9—C8—C13—C120.06 (19)O1—C23—C24—C25−179.92 (15)
C7—C8—C13—C12179.46 (13)O1—C23—C28—C27179.73 (13)
C13—C8—C9—C10−0.7 (2)C23—C24—C25—C260.0 (3)
C7—C8—C9—C10179.95 (16)C24—C25—C26—C270.1 (3)
C9—C8—C13—C14179.71 (13)C25—C26—C27—C28−0.3 (3)
C8—C9—C10—C110.7 (3)C26—C27—C28—C16179.23 (14)
C9—C10—C11—C12−0.1 (3)C26—C27—C28—C230.4 (2)
C10—C11—C12—C13−0.5 (2)N1—C30—C31—C32174.71 (14)
C11—C12—C13—C80.5 (2)N1—C30—C35—C34−173.82 (13)
C11—C12—C13—C14−179.15 (14)C35—C30—C31—C32−1.5 (2)
C12—C13—C14—C15−10.64 (18)N1—C30—C35—O37.05 (19)
C8—C13—C14—C15169.73 (11)C31—C30—C35—C342.4 (2)
C12—C13—C14—C1174.82 (12)C31—C30—C35—O3−176.78 (13)
C8—C13—C14—C1−4.80 (18)C30—C31—C32—C33−0.4 (2)
C1—C14—C15—C16−96.93 (16)C31—C32—C33—C341.4 (3)
C13—C14—C15—N1−164.56 (11)C32—C33—C34—C35−0.5 (3)
C13—C14—C15—C1688.90 (14)C33—C34—C35—C30−1.4 (2)
C1—C14—C15—N19.61 (19)C33—C34—C35—O3177.71 (15)
N1—C15—C16—C17−120.38 (12)
D—H···AD—HH···AD···AD—H···A
C2—H2···N10.932.322.9236 (19)122
C31—H31···O20.932.553.140 (2)122
C5—H5···Cg1i0.932.923.597 (2)130
C26—H26···Cg2v0.932.883.7180 (19)151
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C2—H2⋯N10.932.322.9236 (19)122
C31—H31⋯O20.932.553.140 (2)122
C5—H5⋯Cg1i0.932.923.597 (2)130
C26—H26⋯Cg2ii0.932.883.7180 (19)151

Symmetry codes: (i) ; (ii) . Cg1 and Cg2 are the centroids of the C30–C35 and C8–C13 rings, respectively.

  4 in total

1.  Synthesis of anticancer beta-lactams: mechanism of action.

Authors:  Bimal K Banik; Frederick F Becker; Indrani Banik
Journal:  Bioorg Med Chem       Date:  2004-05-15       Impact factor: 3.641

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  4-(9-Anthr-yl)-1-(4-methoxy-phen-yl)spiro-[azetidin-3,9'-xanthen]-2-one.

Authors:  Mehmet Akkurt; Selvi Karaca; Aliasghar Jarrahpour; Edris Ebrahimi; Orhan Büyükgüngör
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-04-26

4.  4-(9-Anthr-yl)-1-(1-naphth-yl)spiro-[azetidine-3,9'-xanthen]-2-one n-hexane hemisolvate.

Authors:  Mehmet Akkurt; Aliasghar Jarrahpour; Edris Ebrahimi; Mustafa Gençaslan; Orhan Büyükgüngör
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-11-29
  4 in total
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1.  4-(9-Anthr-yl)-1-(2,4-dimethoxy-phen-yl)spiro-[azetidine-3,9'-xanthen]-2-one.

Authors:  Zeliha Baktır; Mehmet Akkurt; Aliasghar Jarrahpour; Edris Ebrahimi; Orhan Büyükgüngör
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-06-20

2.  3-(4-Chloro-phen-oxy)-1-(4-meth-oxy-phen-yl)-4-(4-nitro-phen-yl)azetidin-2-one.

Authors:  Ray J Butcher; Mehmet Akkurt; Aliasghar Jarrahpour; Seid Ali Torabi Badrabady
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-04-13

3.  7-Benzenesulfonamido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]octa-2-ene-2-carboxylic acid monohydrate.

Authors:  Shahzad Sharif; Mehmet Akkurt; Islam Ullah Khan; Manan Ayub Salariya; Sarfraz Ahmad
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-12-09

4.  1-[3-(Morpholin-4-yl)prop-yl]-4-(3-nitro-phen-yl)spiro-[azetidine-3,9'-xanthen]-2-one.

Authors:  Ismail Celik; Mehmet Akkurt; Aliasghar Jarrahpour; Roghayeh Heiran; Namık Ozdemir
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-02-28

5.  1-(Morpholin-4-yl)-4-(2-nitro-phen-yl)spiro-[azetidine-3,9'-xanthen]-2-one.

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-06-14
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