Literature DB >> 21577969

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

Ismail Celik, Mehmet Akkurt, Aliasghar Jarrahpour, Edris Ebrahimi, Orhan Büyükgüngör.   

Abstract

In the title mol-ecule, C(35)H(22)BrNO(2), the four-membered ring of the β-lactam unit is nearly planar [maximum deviation = 0.003 (3) Å] and makes dihedral angles of 87.07 (15), 59.80 (16) and 20.81 (19)°, respectively, with the xanthene system, the anthracene system and the bromo-substituted benzene ring. The mol-ecular conformation is stabilized by weak intra-molecular C-H⋯O and C-H⋯N hydrogen bonds. The crystal structure features weak C-H⋯π inter-actions.

Entities:  

Year:  2009        PMID： 21577969      PMCID： PMC2970342          DOI： 10.1107/S1600536809037830

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


Related literature

For general background to β-lactam anti­biotics, see: Jarrahpour & Khalili (2007 ▶); Landis-Piwowar et al. (2006 ▶); Palomo et al. (2003 ▶); Skiles & McNeil (1990 ▶); Wu & Tormos (1997 ▶). For related structures, see: Akkurt et al. (2006 ▶, 2007 ▶); Akkurt, Jarrahpour et al. (2008 ▶); Akkurt, Karaca et al. (2008 ▶); Pınar et al. (2006 ▶). For geometric analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C35H22BrNO2 M = 568.44 Monoclinic, a = 11.1143 (4) Å b = 19.9412 (5) Å c = 14.0317 (5) Å β = 122.106 (2)° V = 2634.28 (16) Å3 Z = 4 Mo Kα radiation μ = 1.59 mm−1 T = 295 K 0.71 × 0.59 × 0.39 mm

Data collection

Stoe IPDS2 diffractometer Absorption correction: integration (; Stoe & Cie, 2002 ▶) T min = 0.397, T max = 0.575 39287 measured reflections 5424 independent reflections 4308 reflections with I > 2σ(I) R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.122 S = 1.08 5424 reflections 352 parameters H-atom parameters constrained Δρmax = 0.52 e Å−3 Δρmin = −0.74 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/S1600536809037830/is2462sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037830/is2462Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C35H22BrNO2F(000) = 1160
Mr = 568.44Dx = 1.433 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 43756 reflections
a = 11.1143 (4) Åθ = 1.7–28.0°
b = 19.9412 (5) ŵ = 1.59 mm−1
c = 14.0317 (5) ÅT = 295 K
β = 122.106 (2)°Block, light yellow
V = 2634.28 (16) Å30.71 × 0.59 × 0.39 mm
Z = 4
Stoe IPDS2 diffractometer5424 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus4308 reflections with I > 2σ(I)
plane graphiteRint = 0.046
Detector resolution: 6.67 pixels mm-1θmax = 26.5°, θmin = 2.0°
ω scansh = −13→13
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −24→24
Tmin = 0.397, Tmax = 0.575l = −17→17
39287 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0466P)2 + 1.4948P] where P = (Fo2 + 2Fc2)/3
5424 reflections(Δ/σ)max < 0.001
352 parametersΔρmax = 0.52 e Å−3
0 restraintsΔρmin = −0.74 e Å−3
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
Br10.14849 (5)0.25728 (2)0.18916 (4)0.0883 (2)
O10.9308 (2)0.56016 (12)0.3586 (2)0.0757 (8)
O20.6106 (2)0.40529 (10)0.39082 (18)0.0675 (7)
N10.4500 (2)0.47038 (10)0.23373 (18)0.0475 (7)
C10.3676 (3)0.62105 (14)0.2257 (2)0.0543 (8)
C20.3254 (3)0.58361 (19)0.2902 (3)0.0675 (11)
C30.2423 (4)0.6108 (2)0.3248 (3)0.0878 (14)
C40.1913 (4)0.6773 (3)0.2953 (4)0.1023 (18)
C50.2282 (4)0.7145 (2)0.2365 (4)0.0895 (16)
C60.3177 (3)0.68965 (16)0.1994 (3)0.0668 (10)
C70.3553 (4)0.72966 (16)0.1396 (3)0.0732 (11)
C80.4436 (3)0.70807 (14)0.1049 (2)0.0617 (9)
C90.4806 (4)0.74926 (15)0.0411 (3)0.0798 (13)
C100.5646 (5)0.72759 (18)0.0068 (3)0.0841 (14)
C110.6241 (4)0.66303 (17)0.0374 (3)0.0724 (12)
C120.5919 (3)0.62105 (14)0.0967 (2)0.0562 (9)
C130.4974 (3)0.64013 (13)0.1315 (2)0.0500 (8)
C140.4549 (3)0.59686 (12)0.1883 (2)0.0461 (8)
C150.5078 (3)0.52549 (12)0.1999 (2)0.0429 (7)
C160.6615 (3)0.50414 (12)0.3045 (2)0.0451 (7)
C170.7443 (3)0.55389 (13)0.3976 (2)0.0516 (8)
C180.6972 (4)0.57626 (17)0.4658 (3)0.0684 (11)
C190.7729 (5)0.62392 (19)0.5495 (3)0.0836 (14)
C200.8975 (5)0.64880 (19)0.5662 (3)0.0892 (14)
C210.9491 (4)0.62630 (17)0.5034 (3)0.0784 (11)
C220.8721 (3)0.57905 (14)0.4188 (2)0.0595 (9)
C230.8774 (3)0.50458 (15)0.2907 (2)0.0584 (10)
C240.9551 (4)0.4803 (2)0.2475 (3)0.0804 (14)
C250.9094 (4)0.4251 (2)0.1796 (3)0.0851 (16)
C260.7873 (4)0.39262 (19)0.1543 (3)0.0776 (12)
C270.7097 (3)0.41707 (15)0.1974 (3)0.0610 (10)
C280.7521 (3)0.47399 (13)0.2655 (2)0.0485 (8)
C290.5791 (3)0.45045 (13)0.3248 (2)0.0498 (8)
C300.3212 (3)0.43540 (13)0.1680 (2)0.0460 (8)
C310.3017 (3)0.37439 (13)0.2052 (2)0.0500 (8)
C320.1775 (3)0.33946 (14)0.1364 (3)0.0561 (10)
C330.0742 (3)0.36319 (18)0.0326 (3)0.0667 (11)
C340.0942 (3)0.42442 (19)−0.0021 (3)0.0703 (11)
C350.2170 (3)0.46130 (16)0.0651 (2)0.0601 (10)
H20.355400.539400.309000.0810*
H30.218900.585400.368300.1050*
H40.132000.694900.317100.1230*
H50.194900.758400.218700.1070*
H70.319600.773100.121900.0880*
H90.444800.792700.022900.0950*
H100.583900.75500−0.037100.1010*
H110.686700.648900.016500.0870*
H120.632700.578600.115300.0670*
H150.501700.512800.130100.0520*
H180.613300.559100.455400.0820*
H190.739000.638800.593700.1000*
H200.947200.681300.621000.1070*
H211.035300.642300.516700.0940*
H241.038800.501500.264600.0960*
H250.961800.409300.150200.1020*
H260.757100.354700.108800.0930*
H270.626900.395000.180600.0730*
H310.370600.357400.275100.0600*
H33−0.007700.33840−0.013300.0800*
H340.024400.44130−0.071700.0850*
H350.229100.502900.041300.0720*
U11U22U33U12U13U23
Br10.0990 (3)0.0679 (2)0.0934 (3)−0.0370 (2)0.0481 (2)−0.0161 (2)
O10.0685 (14)0.0753 (15)0.0782 (15)−0.0261 (11)0.0355 (13)−0.0033 (12)
O20.0671 (13)0.0592 (12)0.0570 (12)−0.0049 (10)0.0201 (10)0.0178 (10)
N10.0440 (11)0.0440 (11)0.0460 (12)−0.0020 (9)0.0182 (10)0.0036 (9)
C10.0395 (13)0.0594 (16)0.0496 (15)0.0022 (11)0.0140 (12)−0.0148 (13)
C20.0560 (17)0.082 (2)0.0633 (19)−0.0060 (15)0.0310 (16)−0.0190 (16)
C30.062 (2)0.126 (3)0.081 (2)−0.018 (2)0.0418 (19)−0.042 (2)
C40.058 (2)0.139 (4)0.104 (3)0.001 (2)0.039 (2)−0.062 (3)
C50.057 (2)0.095 (3)0.092 (3)0.0152 (19)0.023 (2)−0.041 (2)
C60.0428 (15)0.0620 (18)0.067 (2)0.0086 (13)0.0099 (14)−0.0245 (16)
C70.066 (2)0.0451 (16)0.072 (2)0.0148 (14)0.0120 (17)−0.0073 (15)
C80.0629 (17)0.0399 (14)0.0537 (17)0.0027 (12)0.0116 (14)−0.0003 (12)
C90.095 (3)0.0402 (16)0.065 (2)−0.0026 (15)0.0160 (19)0.0091 (14)
C100.119 (3)0.058 (2)0.065 (2)−0.017 (2)0.042 (2)0.0067 (16)
C110.091 (2)0.065 (2)0.063 (2)−0.0138 (17)0.0422 (19)−0.0021 (16)
C120.0659 (17)0.0474 (15)0.0535 (16)−0.0011 (12)0.0305 (14)0.0029 (12)
C130.0519 (14)0.0396 (13)0.0429 (14)0.0033 (11)0.0146 (12)−0.0009 (11)
C140.0417 (13)0.0425 (13)0.0392 (13)0.0026 (10)0.0114 (11)−0.0028 (10)
C150.0440 (13)0.0397 (12)0.0397 (13)0.0024 (10)0.0186 (11)0.0008 (10)
C160.0416 (13)0.0400 (12)0.0423 (13)0.0007 (10)0.0146 (11)0.0035 (10)
C170.0531 (15)0.0422 (13)0.0418 (14)0.0028 (11)0.0133 (12)0.0013 (11)
C180.0655 (19)0.070 (2)0.0535 (17)0.0061 (15)0.0206 (15)−0.0107 (15)
C190.100 (3)0.077 (2)0.0517 (19)0.015 (2)0.0255 (19)−0.0099 (17)
C200.109 (3)0.064 (2)0.053 (2)−0.014 (2)0.015 (2)−0.0081 (16)
C210.079 (2)0.0619 (19)0.0574 (19)−0.0243 (17)0.0113 (18)0.0043 (16)
C220.0601 (17)0.0477 (15)0.0503 (16)−0.0085 (13)0.0155 (14)0.0069 (12)
C230.0534 (16)0.0610 (17)0.0547 (17)0.0040 (13)0.0247 (14)0.0127 (13)
C240.061 (2)0.106 (3)0.078 (2)0.0084 (19)0.0396 (19)0.022 (2)
C250.081 (3)0.113 (3)0.070 (2)0.037 (2)0.046 (2)0.018 (2)
C260.087 (2)0.077 (2)0.060 (2)0.0271 (19)0.0331 (18)0.0004 (16)
C270.0577 (17)0.0576 (17)0.0567 (17)0.0084 (13)0.0229 (14)−0.0045 (13)
C280.0445 (13)0.0453 (13)0.0477 (14)0.0081 (11)0.0191 (12)0.0074 (11)
C290.0524 (15)0.0448 (14)0.0446 (14)−0.0014 (11)0.0207 (12)0.0011 (11)
C300.0424 (13)0.0476 (14)0.0470 (14)−0.0026 (10)0.0231 (12)−0.0064 (11)
C310.0509 (14)0.0525 (15)0.0471 (15)−0.0047 (11)0.0263 (12)−0.0054 (12)
C320.0595 (17)0.0579 (16)0.0585 (18)−0.0134 (13)0.0364 (15)−0.0165 (13)
C330.0526 (17)0.087 (2)0.0598 (19)−0.0195 (16)0.0294 (15)−0.0208 (17)
C340.0510 (17)0.091 (2)0.0540 (18)−0.0013 (16)0.0179 (15)0.0008 (17)
C350.0481 (15)0.0654 (18)0.0539 (17)−0.0017 (13)0.0184 (13)0.0013 (14)
Br1—C321.895 (3)C23—C241.380 (6)
O1—C221.366 (4)C23—C281.383 (5)
O1—C231.374 (4)C24—C251.365 (5)
O2—C291.203 (3)C25—C261.369 (7)
N1—C151.473 (4)C26—C271.379 (6)
N1—C291.379 (4)C27—C281.395 (4)
N1—C301.408 (4)C30—C311.386 (4)
C1—C21.431 (5)C30—C351.384 (4)
C1—C61.448 (4)C31—C321.381 (5)
C1—C141.411 (5)C32—C331.373 (5)
C2—C31.364 (6)C33—C341.376 (5)
C3—C41.415 (7)C34—C351.387 (5)
C4—C51.326 (7)C2—H20.9300
C5—C61.434 (6)C3—H30.9300
C6—C71.374 (5)C4—H40.9300
C7—C81.376 (6)C5—H50.9300
C8—C91.427 (5)C7—H70.9300
C8—C131.448 (4)C9—H90.9300
C9—C101.330 (7)C10—H100.9300
C10—C111.406 (5)C11—H110.9300
C11—C121.356 (5)C12—H120.9300
C12—C131.425 (5)C15—H150.9800
C13—C141.415 (4)C18—H180.9300
C14—C151.515 (4)C19—H190.9300
C15—C161.609 (4)C20—H200.9300
C16—C171.503 (3)C21—H210.9300
C16—C281.504 (5)C24—H240.9300
C16—C291.531 (4)C25—H250.9300
C17—C181.386 (5)C26—H260.9300
C17—C221.382 (5)C27—H270.9300
C18—C191.393 (5)C31—H310.9300
C19—C201.369 (8)C33—H330.9300
C20—C211.358 (7)C34—H340.9300
C21—C221.396 (4)C35—H350.9300
Br1···C21i3.491 (4)C29···H22.9600
O2···C313.073 (4)C30···H22.7500
O2···H312.4600C30···H11ix3.0500
O2···H7i2.7800C31···H19ii3.1000
O2···H9i2.7700C32···H25vii2.8700
O2···H3ii2.8700C33···H11ix3.0900
N1···C22.968 (4)C33···H25vii2.7100
N1···C273.359 (5)C34···H11ix2.9400
N1···H22.3000C35···H152.9700
N1···H272.8700C35···H11ix2.9300
C1···C183.528 (5)H2···N12.3000
C2···N12.968 (4)H2···C152.8400
C2···C183.514 (6)H2···C292.9600
C2···C303.405 (5)H2···C302.7500
C4···C9iii3.548 (6)H2···H182.5200
C9···C4iv3.548 (6)H3···H24vii2.4100
C12···C163.484 (4)H3···O2ii2.8700
C12···C283.591 (4)H5···H72.4200
C14···C353.525 (4)H7···H52.4200
C14···C183.382 (4)H7···H92.4600
C16···C123.484 (4)H7···O2vi2.7800
C18···C143.382 (4)H9···H72.4600
C18···C23.514 (6)H9···O2vi2.7700
C18···C13.528 (5)H9···C4iv2.9900
C19···C24v3.524 (6)H10···C19iv3.0000
C20···C25v3.371 (5)H11···C30ix3.0500
C20···C24v3.405 (5)H11···C33ix3.0900
C21···C23v3.599 (4)H11···C34ix2.9400
C21···Br1vi3.491 (4)H11···C35ix2.9300
C23···C21v3.599 (4)H12···C152.4900
C24···C20v3.405 (5)H12···C162.9100
C24···C19v3.524 (6)H12···C232.9200
C25···C20v3.371 (5)H12···C282.7500
C27···N13.359 (5)H12···H152.0500
C28···C123.591 (4)H15···C122.5300
C30···C23.405 (5)H15···C272.7500
C31···O23.073 (4)H15···C352.9700
C35···C143.525 (4)H15···H122.0500
C2···H182.8200H15···H352.6000
C3···H24vii2.9200H18···C22.8200
C4···H9iii2.9900H18···C292.7300
C5···H33viii2.9600H18···H22.5200
C6···H33viii3.0700H19···C31ii3.1000
C8···H26ix2.9000H24···C3x2.9200
C9···H31vi3.0800H24···H3x2.4100
C11···H27ix3.0700H25···C32x2.8700
C12···H152.5300H25···C33x2.7100
C13···H26ix3.0400H26···C8ix2.9000
C14···H352.9300H26···C13ix3.0400
C15···H122.4900H27···N12.8700
C15···H273.0000H27···C153.0000
C15···H22.8400H27···C292.6000
C15···H352.7200H27···C11ix3.0700
C16···H122.9100H31···O22.4600
C19···H10iii3.0000H31···C292.7500
C23···H122.9200H31···C9i3.0800
C24···H34ix3.0300H33···C5viii2.9600
C25···H35ix2.9900H33···C6viii3.0700
C27···H152.7500H34···C24ix3.0300
C28···H122.7500H35···C142.9300
C29···H272.6000H35···C152.7200
C29···H182.7300H35···H152.6000
C29···H312.7500H35···C25ix2.9900
C22—O1—C23118.6 (3)O2—C29—C16135.1 (3)
C15—N1—C2995.5 (2)N1—C29—C1693.3 (2)
C15—N1—C30128.6 (2)N1—C30—C31119.8 (2)
C29—N1—C30131.2 (2)N1—C30—C35119.6 (3)
C2—C1—C6116.4 (3)C31—C30—C35120.6 (3)
C2—C1—C14125.3 (3)C30—C31—C32118.6 (3)
C6—C1—C14118.3 (3)Br1—C32—C31118.5 (2)
C1—C2—C3122.0 (3)Br1—C32—C33119.5 (3)
C2—C3—C4120.7 (4)C31—C32—C33122.0 (3)
C3—C4—C5119.9 (5)C32—C33—C34118.7 (3)
C4—C5—C6122.4 (4)C33—C34—C35121.0 (3)
C1—C6—C5118.7 (3)C30—C35—C34119.1 (3)
C1—C6—C7120.3 (3)C1—C2—H2119.00
C5—C6—C7121.1 (3)C3—C2—H2119.00
C6—C7—C8122.7 (3)C2—C3—H3120.00
C7—C8—C9122.6 (3)C4—C3—H3120.00
C7—C8—C13118.4 (3)C3—C4—H4120.00
C9—C8—C13118.9 (3)C5—C4—H4120.00
C8—C9—C10122.1 (3)C4—C5—H5119.00
C9—C10—C11119.6 (4)C6—C5—H5119.00
C10—C11—C12121.2 (4)C6—C7—H7119.00
C11—C12—C13121.9 (3)C8—C7—H7119.00
C8—C13—C12116.1 (3)C8—C9—H9119.00
C8—C13—C14120.0 (3)C10—C9—H9119.00
C12—C13—C14123.9 (3)C9—C10—H10120.00
C1—C14—C13120.2 (2)C11—C10—H10120.00
C1—C14—C15125.8 (3)C10—C11—H11119.00
C13—C14—C15114.0 (3)C12—C11—H11119.00
N1—C15—C14121.6 (3)C11—C12—H12119.00
N1—C15—C1686.68 (19)C13—C12—H12119.00
C14—C15—C16120.7 (2)N1—C15—H15109.00
C15—C16—C17118.7 (2)C14—C15—H15109.00
C15—C16—C28111.4 (2)C16—C15—H15109.00
C15—C16—C2984.5 (2)C17—C18—H18119.00
C17—C16—C28111.2 (3)C19—C18—H18119.00
C17—C16—C29116.8 (2)C18—C19—H19120.00
C28—C16—C29111.8 (2)C20—C19—H19120.00
C16—C17—C18122.1 (3)C19—C20—H20120.00
C16—C17—C22120.8 (3)C21—C20—H20120.00
C18—C17—C22117.2 (3)C20—C21—H21120.00
C17—C18—C19121.4 (4)C22—C21—H21120.00
C18—C19—C20119.6 (5)C23—C24—H24120.00
C19—C20—C21120.5 (4)C25—C24—H24120.00
C20—C21—C22119.7 (4)C24—C25—H25120.00
O1—C22—C17122.7 (2)C26—C25—H25120.00
O1—C22—C21115.7 (3)C25—C26—H26121.00
C17—C22—C21121.6 (3)C27—C26—H26120.00
O1—C23—C24116.6 (3)C26—C27—H27119.00
O1—C23—C28122.6 (3)C28—C27—H27119.00
C24—C23—C28120.9 (3)C30—C31—H31121.00
C23—C24—C25120.1 (4)C32—C31—H31121.00
C24—C25—C26120.8 (4)C32—C33—H33121.00
C25—C26—C27118.9 (3)C34—C33—H33121.00
C26—C27—C28121.7 (4)C33—C34—H34119.00
C16—C28—C23120.6 (2)C35—C34—H34120.00
C16—C28—C27121.8 (3)C30—C35—H35120.00
C23—C28—C27117.5 (3)C34—C35—H35120.00
O2—C29—N1131.5 (3)
C23—O1—C22—C21166.8 (3)C14—C15—C16—C177.2 (4)
C22—O1—C23—C24−168.8 (3)N1—C15—C16—C17−118.0 (3)
C22—O1—C23—C2811.5 (4)N1—C15—C16—C28110.9 (2)
C23—O1—C22—C17−13.8 (4)C14—C15—C16—C29124.8 (3)
C29—N1—C30—C3113.3 (5)C14—C15—C16—C28−123.9 (3)
C29—N1—C30—C35−164.7 (3)C29—C16—C28—C2733.9 (3)
C29—N1—C15—C160.4 (2)C29—C16—C28—C23−150.1 (2)
C15—N1—C30—C35−14.9 (5)C15—C16—C28—C27−58.7 (3)
C30—N1—C15—C1478.4 (3)C15—C16—C29—O2177.7 (4)
C15—N1—C29—C16−0.4 (2)C15—C16—C28—C23117.3 (3)
C30—N1—C15—C16−157.3 (3)C28—C16—C17—C18−164.1 (3)
C29—N1—C15—C14−123.9 (2)C28—C16—C17—C2215.6 (3)
C30—N1—C29—C16156.3 (3)C29—C16—C17—C18−34.3 (4)
C15—N1—C30—C31163.1 (3)C29—C16—C17—C22145.5 (3)
C15—N1—C29—O2−177.8 (3)C15—C16—C17—C1864.6 (4)
C30—N1—C29—O2−21.1 (5)C17—C16—C28—C23−17.7 (3)
C2—C1—C14—C13−175.7 (3)C17—C16—C28—C27166.4 (3)
C2—C1—C6—C7178.8 (3)C15—C16—C29—N10.4 (2)
C6—C1—C14—C15−175.1 (3)C15—C16—C17—C22−115.6 (3)
C14—C1—C6—C5179.6 (3)C28—C16—C29—N1−110.5 (2)
C2—C1—C6—C5−1.5 (5)C28—C16—C29—O266.7 (4)
C14—C1—C6—C7−0.1 (5)C17—C16—C29—O2−62.8 (5)
C14—C1—C2—C3179.0 (3)C17—C16—C29—N1119.9 (3)
C6—C1—C14—C133.1 (4)C16—C17—C22—C21178.7 (3)
C6—C1—C2—C30.2 (5)C22—C17—C18—C192.3 (5)
C2—C1—C14—C156.2 (5)C18—C17—C22—O1179.0 (3)
C1—C2—C3—C41.6 (6)C16—C17—C18—C19−178.0 (3)
C2—C3—C4—C5−2.2 (7)C18—C17—C22—C21−1.6 (4)
C3—C4—C5—C60.9 (7)C16—C17—C22—O1−0.7 (4)
C4—C5—C6—C11.0 (6)C17—C18—C19—C20−0.8 (5)
C4—C5—C6—C7−179.3 (4)C18—C19—C20—C21−1.4 (6)
C1—C6—C7—C8−1.9 (5)C19—C20—C21—C222.1 (5)
C5—C6—C7—C8178.4 (4)C20—C21—C22—C17−0.6 (5)
C6—C7—C8—C130.8 (5)C20—C21—C22—O1178.9 (3)
C6—C7—C8—C9178.9 (3)O1—C23—C24—C25179.8 (3)
C7—C8—C13—C142.3 (4)C28—C23—C24—C25−0.5 (5)
C7—C8—C9—C10−179.1 (4)O1—C23—C28—C165.1 (4)
C13—C8—C9—C10−1.1 (5)C24—C23—C28—C16−174.6 (3)
C9—C8—C13—C123.7 (4)C24—C23—C28—C271.5 (4)
C7—C8—C13—C12−178.1 (3)O1—C23—C28—C27−178.8 (3)
C9—C8—C13—C14−175.9 (3)C23—C24—C25—C26−0.7 (6)
C8—C9—C10—C11−2.5 (6)C24—C25—C26—C270.8 (6)
C9—C10—C11—C123.3 (6)C25—C26—C27—C280.3 (5)
C10—C11—C12—C13−0.4 (5)C26—C27—C28—C16174.7 (3)
C11—C12—C13—C8−3.1 (4)C26—C27—C28—C23−1.4 (5)
C11—C12—C13—C14176.6 (3)N1—C30—C31—C32−176.6 (3)
C12—C13—C14—C15−5.5 (4)C35—C30—C31—C321.3 (5)
C8—C13—C14—C15174.2 (2)N1—C30—C35—C34176.0 (3)
C12—C13—C14—C1176.2 (3)C31—C30—C35—C34−1.9 (5)
C8—C13—C14—C1−4.2 (4)C30—C31—C32—Br1−178.2 (3)
C1—C14—C15—N111.7 (4)C30—C31—C32—C330.5 (5)
C1—C14—C15—C16−94.9 (4)Br1—C32—C33—C34177.0 (3)
C13—C14—C15—C1686.9 (3)C31—C32—C33—C34−1.7 (6)
C13—C14—C15—N1−166.5 (2)C32—C33—C34—C351.1 (6)
N1—C15—C16—C29−0.37 (19)C33—C34—C35—C300.7 (5)
D—H···AD—HH···AD···AD—H···A
C2—H2···N10.932.302.968 (4)128
C31—H31···O20.932.463.073 (4)123
C11—H11···Cg2ix0.932.753.653 (5)164
C26—H26···Cg1ix0.932.963.616 (4)129
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C2—H2⋯N10.932.302.968 (4)128
C31—H31⋯O20.932.463.073 (4)123
C11—H11⋯Cg2i0.932.753.653 (5)164
C26—H26⋯Cg1i0.932.963.616 (4)129

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

  5 in total

1.  A short history of SHELX.

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

2.  Apoptotic-inducing activity of novel polycyclic aromatic compounds in human leukemic cells.

Authors:  Kristin R Landis-Piwowar; Di Chen; Qiuzhi Cindy Cui; Vesna Minic; Frederick F Becker; Bimal K Banik; Q Ping Dou
Journal:  Int J Mol Med       Date:  2006-05       Impact factor: 4.101

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.  Development of a new family of conformationally restricted peptides as potent nucleators of beta-turns. Design, synthesis, structure, and biological evaluation of a beta-lactam peptide analogue of melanostatin.

Authors:  Claudio Palomo; Jesus M Aizpurua; Ana Benito; José Ignacio Miranda; Raluca M Fratila; Carlos Matute; Maria Domercq; Federico Gago; Sonsoles Martin-Santamaria; Anthony Linden
Journal:  J Am Chem Soc       Date:  2003-12-31       Impact factor: 15.419

5.  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
  5 in total
  7 in total

1.  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

2.  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

3.  7-Bromo-9-(2-hy-droxy-4,4-dimethyl-6-oxocyclo-hex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetra-hydro-1H-xanthen-1-one.

Authors:  Shaaban K Mohamed; Mehmet Akkurt; Antar A Abdelhamid; Phillip E Fanwick; Herman Potgeiter
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-05-12

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.  Synthesis of some new mono- and bis-polycyclic aromatic spiro and bis-nonspiro-beta-lactams.

Authors:  Aliasghar Jarrahpour; Edris Ebrahimi
Journal:  Molecules       Date:  2010-01-22       Impact factor: 4.411

6.  12-(2-Hy-droxy-6-oxo-cyclo-hex-1-en-yl)-9,10-di-hydro-8H-benzo[a]xanthen-11(12H)-one.

Authors:  Mehmet Akkurt; Shaaban K Mohamed; Alan R Kennedy; Antar A Abdelhamid; Gary J Miller; Mustafa R Albayati
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-09-18

7.  1-(Morpholin-4-yl)-4-(2-nitro-phen-yl)spiro-[azetidine-3,9'-xanthen]-2-one.

Authors:  Zeliha Atioğlu; Mehmet Akkurt; Aliasghar Jarrahpour; Roghayeh Heiran; Namık Ozdemir
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-06-14
  7 in total

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