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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o851–o852.
Published online 2008 April 16. doi:  10.1107/S1600536808008829
PMCID: PMC2961224

1-(4-Methoxy­phen­yl)-7-phenyl-3-(phenyl­selenylmeth­yl)perhydro­isoxazolo[2′,3′:1,2]pyrrolo[3,4-b]azetidine-6-spiro-2′-chroman-2,4′-dione

Abstract

In the title compound, C35H30N2O5Se, the pyrrolidine ring adopts an envelope conformation and the oxazolidine ring is in a twist conformation. The tetra­hydro­pyran ring adopts a half-chair conformation. The methoxy­phenyl ring is twisted away from the attached azetidinone ring by 15.7 (1)°. In the crystal structure, inter­molecular C—H(...)O inter­actions link the mol­ecules into a two-dimensional network.

Related literature

For general background, see: Brakhage (1998 [triangle]); Chenera et al. (1993 [triangle]); Ellis (1997 [triangle]); Farrugia (1997 [triangle]); Kilonda et al. (1995 [triangle]); Koojiman et al. (1984 [triangle]); Lampronti et al. (2003 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For ring conformation details, see: Cremer & Pople (1975 [triangle]); Nardelli (1983 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o851-scheme1.jpg

Experimental

Crystal data

  • C35H30N2O5Se
  • M r = 637.57
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o851-efi1.jpg
  • a = 14.0886 (5) Å
  • b = 10.6813 (4) Å
  • c = 19.4744 (7) Å
  • β = 92.721 (2)°
  • V = 2927.29 (18) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.33 mm−1
  • T = 293 (2) K
  • 0.30 × 0.20 × 0.20 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (Blessing, 1995 [triangle]) T min = 0.691, T max = 0.777
  • 38750 measured reflections
  • 9941 independent reflections
  • 5805 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.116
  • S = 1.01
  • 9941 reflections
  • 389 parameters
  • H-atom parameters constrained
  • Δρmax = 0.79 e Å−3
  • Δρmin = −0.67 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008829/ci2571sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008829/ci2571Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

ETSK thanks Professor M. N. Ponnuswamy and Professor D. Velmurugan, Department of Crystallography and Bio­physics, University of Madras, India, for their guidance and valuable suggestions. ETSK also thanks SRM management, India, for their support.

supplementary crystallographic information

Comment

Chromanones are found to exhibit strong activity in inhibiting in vitro cell growth of human tumour cells (Lampronti et al., 2003). Many chromanone derivatives are versatile intermediates for the synthesis of natural products such as brazillin, hematoxylin, ripariochromene, clausenin, calonlide A and inophyllum B (Koojiman et al.,1984; Ellis et al., 1997; Chenera et al., 1993). Pyrrolidines and pyrroles are common structural motifs in drugs and drug candidates owing to their ability to act as selective glycosidase inhibitors which are used in the treatment of diabetes, cancer, malaria and viral infections including AIDS (Kilonda et al.,1995). The most commonly used β-lactam antibiotics for the therapy of infectious diseases are penicillin and cephalosporin (Brakhage, 1998). In view of the above, the crystal structure determination of the title compound was carried out and the results are presented here.

Bond lengths of the title compound (Fig. 1) show normal values (Allen et al., 1987). The pyrrolidine ring (N2/C4/C2/C3/C5) adopts an envelope conformation with an asymmetry parameter (Nardelli,1983) ΔCs(N2) of 3.8 (2)° and puckering parameters (Cremer and Pople, 1975) of q2 = 0.366 (2) Å and [var phi]2 = 184.9 (3)°. The oxazolidine ring (O2/N2/C5/C7/C6) is in a twist conformation with an asymmetry parameter ΔC2(O2) of 8.9 (2)° and puckering parameters q2 = 0.329 (2) Å and [var phi]2 = 262.2 (3)°. The sums of bond angles around atom N1 (359.7°) and N2 (324.5°) indicate sp2 and sp3 hybridization, respectively. The tetrahydropyran ring adopts a half-chair conformation. The dihedral angle between the azetidinone ring and the attached methoxyphenyl ring is 15.7 (1)°.

In the crystal packing, intermolecular C—H···O interactions (Table 1) link the molecules into a two-dimensional network (Fig. 2).

Experimental

To a solution of the bicyclic nitrone (1 mol) in dry acetonitrile (20 ml) was added 3-arylidene chromanone (1 mol) under a N2 atmosphere. The reaction was refluxed for 4 h. After the completion of the reaction, the solvent was distilled off under reduced pressure and the crude product was purified by column chromatography. The title compound was crystallized from benzene solution by slow evaporation technique.

Refinement

H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C-H = 0.93-0.98 Å and Uiso(H)= 1.2–1.5Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound with 30% probability displacement ellipsoids.
Fig. 2.
A view of the molecular packing of the title compound.

Crystal data

C35H30N2O5SeF000 = 1312
Mr = 637.57Dx = 1.447 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 38750 reflections
a = 14.0886 (5) Åθ = 1.8–31.9º
b = 10.6813 (4) ŵ = 1.33 mm1
c = 19.4744 (7) ÅT = 293 (2) K
β = 92.721 (2)ºPrism, colourless
V = 2927.29 (18) Å30.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker KappaAPEX2 diffractometer9941 independent reflections
Radiation source: fine-focus sealed tube5805 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.028
T = 293(2) Kθmax = 31.9º
ω and [var phi] scansθmin = 1.8º
Absorption correction: multi-scan(Blessing, 1995)h = −19→20
Tmin = 0.691, Tmax = 0.777k = −15→10
38750 measured reflectionsl = −28→28

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.116  w = 1/[σ2(Fo2) + (0.0444P)2 + 1.2941P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
9941 reflectionsΔρmax = 0.79 e Å3
389 parametersΔρmin = −0.67 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
Se11.016999 (16)0.19600 (3)0.180072 (11)0.05427 (9)
O10.84548 (10)0.24863 (15)0.33002 (7)0.0499 (4)
O20.69775 (9)0.13919 (14)0.07844 (6)0.0423 (3)
O30.64805 (13)0.40844 (15)0.12826 (7)0.0583 (4)
O40.54329 (11)0.16190 (14)−0.01690 (7)0.0482 (4)
O50.42581 (12)0.20236 (17)0.48343 (9)0.0662 (5)
N10.71402 (11)0.11790 (15)0.30571 (7)0.0353 (3)
N20.74055 (11)0.06570 (15)0.13393 (7)0.0358 (3)
C10.80284 (13)0.16622 (18)0.30008 (9)0.0359 (4)
C20.82270 (13)0.07814 (18)0.24043 (9)0.0357 (4)
H20.87490.01890.24970.043*
C30.72246 (13)0.02471 (18)0.25094 (9)0.0354 (4)
H30.7221−0.06230.26690.042*
C40.81961 (13)0.13643 (18)0.16898 (9)0.0343 (4)
H40.80390.22560.17140.041*
C50.66549 (13)0.04692 (18)0.18298 (9)0.0346 (4)
H50.6280−0.02760.17040.041*
C60.60958 (12)0.19551 (17)0.09998 (9)0.0322 (4)
C70.60343 (12)0.16392 (17)0.17651 (9)0.0324 (4)
H70.63590.23080.20280.039*
C80.62051 (13)0.33430 (18)0.08468 (9)0.0352 (4)
C90.60212 (13)0.36900 (18)0.01199 (9)0.0357 (4)
C100.62385 (15)0.4882 (2)−0.01152 (11)0.0458 (5)
H100.64560.54900.01950.055*
C110.61339 (18)0.5166 (2)−0.08025 (12)0.0552 (6)
H110.62830.5963−0.09570.066*
C120.58075 (18)0.4265 (2)−0.12602 (11)0.0580 (6)
H120.57430.4459−0.17260.070*
C130.55774 (17)0.3095 (2)−0.10459 (11)0.0525 (6)
H130.53550.2498−0.13620.063*
C140.56779 (14)0.27993 (19)−0.03503 (10)0.0396 (4)
C150.52914 (14)0.1432 (2)0.05444 (10)0.0421 (4)
H15A0.52320.05420.06330.051*
H15B0.47020.18300.06610.051*
C160.50369 (13)0.1537 (2)0.20162 (10)0.0412 (4)
C170.45117 (18)0.0450 (3)0.19745 (14)0.0660 (7)
H170.4770−0.02620.17810.079*
C180.3608 (2)0.0404 (4)0.22162 (16)0.0898 (11)
H180.3265−0.03390.21860.108*
C190.3214 (2)0.1434 (5)0.24973 (16)0.0944 (12)
H190.26040.13960.26590.113*
C200.3719 (2)0.2522 (4)0.25400 (15)0.0848 (10)
H200.34500.32290.27300.102*
C210.46266 (16)0.2584 (3)0.23037 (12)0.0561 (6)
H210.49650.33310.23370.067*
C220.64158 (13)0.13740 (18)0.35180 (9)0.0355 (4)
C230.57163 (15)0.0489 (2)0.35695 (10)0.0455 (5)
H230.5739−0.02400.33090.055*
C240.49788 (16)0.0667 (2)0.40035 (11)0.0491 (5)
H240.45070.00630.40350.059*
C250.49483 (14)0.1746 (2)0.43884 (10)0.0448 (5)
C260.56613 (15)0.2627 (2)0.43419 (11)0.0474 (5)
H260.56470.33480.46080.057*
C270.63907 (14)0.2453 (2)0.39089 (10)0.0424 (4)
H270.68640.30550.38790.051*
C280.34568 (18)0.1226 (3)0.48395 (15)0.0736 (8)
H28A0.30160.15440.51580.110*
H28B0.36550.04000.49770.110*
H28C0.31560.11940.43870.110*
C290.90857 (14)0.1174 (2)0.13028 (10)0.0441 (5)
H29A0.90030.15400.08480.053*
H29B0.92050.02860.12500.053*
C301.11387 (14)0.1421 (2)0.12143 (10)0.0423 (4)
C311.12365 (18)0.0189 (2)0.10270 (15)0.0628 (7)
H311.0823−0.04120.11870.075*
C321.19504 (19)−0.0161 (3)0.05994 (17)0.0766 (8)
H321.2007−0.09940.04680.092*
C331.25653 (18)0.0703 (3)0.03718 (14)0.0715 (8)
H331.30500.04610.00920.086*
C341.24733 (17)0.1910 (3)0.05514 (14)0.0641 (7)
H341.28930.25020.03910.077*
C351.17647 (15)0.2283 (2)0.09712 (12)0.0523 (5)
H351.17100.31220.10900.063*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Se10.04250 (13)0.07341 (18)0.04728 (13)0.00234 (11)0.00606 (9)−0.01202 (11)
O10.0460 (8)0.0529 (9)0.0506 (8)−0.0080 (7)0.0006 (7)−0.0064 (7)
O20.0403 (7)0.0574 (9)0.0294 (6)0.0159 (6)0.0042 (5)−0.0001 (6)
O30.0896 (12)0.0422 (9)0.0416 (8)−0.0170 (8)−0.0122 (8)−0.0078 (7)
O40.0623 (9)0.0430 (8)0.0380 (7)−0.0094 (7)−0.0108 (6)−0.0066 (6)
O50.0488 (9)0.0835 (13)0.0684 (11)−0.0043 (8)0.0253 (8)−0.0200 (9)
N10.0391 (8)0.0353 (9)0.0317 (7)0.0000 (7)0.0052 (6)−0.0020 (6)
N20.0373 (8)0.0384 (9)0.0318 (7)0.0091 (7)0.0030 (6)−0.0002 (6)
C10.0366 (10)0.0386 (11)0.0324 (8)0.0039 (8)0.0002 (7)0.0068 (8)
C20.0367 (9)0.0369 (11)0.0337 (8)0.0093 (8)0.0030 (7)0.0043 (8)
C30.0426 (10)0.0296 (9)0.0343 (8)0.0053 (8)0.0064 (7)0.0023 (7)
C40.0346 (9)0.0366 (10)0.0320 (8)0.0071 (8)0.0037 (7)0.0019 (7)
C50.0356 (9)0.0316 (10)0.0368 (9)0.0018 (7)0.0043 (7)−0.0045 (7)
C60.0291 (8)0.0354 (10)0.0319 (8)0.0033 (7)−0.0003 (6)−0.0067 (7)
C70.0290 (8)0.0338 (10)0.0346 (8)0.0012 (7)0.0026 (7)−0.0051 (7)
C80.0329 (9)0.0366 (10)0.0359 (9)−0.0005 (8)−0.0018 (7)−0.0051 (8)
C90.0328 (9)0.0370 (11)0.0370 (9)0.0044 (8)−0.0031 (7)−0.0028 (8)
C100.0509 (12)0.0403 (12)0.0460 (11)0.0000 (9)−0.0015 (9)−0.0025 (9)
C110.0664 (15)0.0471 (13)0.0518 (12)0.0032 (11)−0.0001 (11)0.0106 (11)
C120.0684 (16)0.0632 (16)0.0415 (11)0.0064 (13)−0.0073 (10)0.0058 (11)
C130.0604 (14)0.0559 (15)0.0397 (10)0.0007 (11)−0.0131 (10)−0.0056 (10)
C140.0369 (10)0.0424 (12)0.0386 (9)0.0031 (8)−0.0077 (8)−0.0047 (8)
C150.0442 (11)0.0393 (11)0.0422 (10)−0.0072 (9)−0.0047 (8)−0.0056 (9)
C160.0327 (10)0.0552 (13)0.0360 (9)0.0011 (9)0.0044 (7)−0.0014 (9)
C170.0502 (14)0.0756 (18)0.0733 (16)−0.0166 (13)0.0132 (12)−0.0070 (14)
C180.0539 (17)0.138 (3)0.0782 (19)−0.0374 (19)0.0110 (15)0.004 (2)
C190.0363 (14)0.181 (4)0.0671 (18)0.004 (2)0.0132 (12)0.010 (2)
C200.0533 (17)0.134 (3)0.0680 (17)0.0316 (19)0.0163 (14)−0.0062 (19)
C210.0462 (13)0.0687 (16)0.0539 (12)0.0178 (11)0.0093 (10)−0.0033 (12)
C220.0382 (10)0.0385 (11)0.0299 (8)0.0018 (8)0.0021 (7)0.0019 (8)
C230.0525 (12)0.0419 (12)0.0431 (10)−0.0058 (9)0.0124 (9)−0.0067 (9)
C240.0471 (12)0.0500 (13)0.0512 (12)−0.0109 (10)0.0115 (9)−0.0024 (10)
C250.0365 (10)0.0601 (14)0.0384 (10)0.0029 (9)0.0075 (8)−0.0040 (9)
C260.0467 (12)0.0502 (13)0.0457 (11)−0.0004 (10)0.0073 (9)−0.0151 (10)
C270.0419 (11)0.0432 (11)0.0424 (10)−0.0050 (9)0.0049 (8)−0.0083 (9)
C280.0448 (14)0.099 (2)0.0793 (18)−0.0042 (14)0.0260 (12)−0.0061 (16)
C290.0366 (10)0.0604 (14)0.0359 (9)0.0025 (9)0.0062 (8)−0.0018 (9)
C300.0331 (10)0.0500 (12)0.0437 (10)0.0037 (9)−0.0003 (8)−0.0039 (9)
C310.0492 (13)0.0477 (14)0.0919 (19)−0.0018 (11)0.0087 (13)−0.0055 (13)
C320.0586 (16)0.0615 (17)0.110 (2)0.0086 (13)0.0066 (15)−0.0344 (16)
C330.0411 (13)0.099 (2)0.0751 (17)−0.0032 (14)0.0079 (12)−0.0348 (16)
C340.0431 (13)0.085 (2)0.0653 (15)−0.0131 (12)0.0090 (11)−0.0100 (14)
C350.0420 (12)0.0548 (14)0.0601 (13)−0.0032 (10)0.0028 (10)−0.0081 (11)

Geometric parameters (Å, °)

Se1—C301.910 (2)C13—H130.93
Se1—C291.959 (2)C15—H15A0.97
O1—C11.201 (2)C15—H15B0.97
O2—N21.4441 (19)C16—C171.377 (3)
O2—C61.460 (2)C16—C211.389 (3)
O3—C81.211 (2)C17—C181.379 (4)
O4—C141.358 (2)C17—H170.93
O4—C151.427 (2)C18—C191.359 (5)
O5—C251.367 (2)C18—H180.93
O5—C281.414 (3)C19—C201.364 (5)
N1—C11.363 (2)C19—H190.93
N1—C221.406 (2)C20—C211.381 (4)
N1—C31.468 (2)C20—H200.93
N2—C51.472 (2)C21—H210.93
N2—C41.485 (2)C22—C231.373 (3)
C1—C21.531 (3)C22—C271.382 (3)
C2—C41.523 (2)C23—C241.383 (3)
C2—C31.546 (3)C23—H230.93
C2—H20.98C24—C251.376 (3)
C3—C51.533 (3)C24—H240.93
C3—H30.98C25—C261.382 (3)
C4—C291.506 (3)C26—C271.372 (3)
C4—H40.98C26—H260.93
C5—C71.527 (3)C27—H270.93
C5—H50.98C28—H28A0.96
C6—C151.513 (2)C28—H28B0.96
C6—C81.521 (3)C28—H28C0.96
C6—C71.535 (2)C29—H29A0.97
C7—C161.513 (2)C29—H29B0.97
C7—H70.98C30—C311.374 (3)
C8—C91.474 (3)C30—C351.375 (3)
C9—C141.391 (3)C31—C321.387 (4)
C9—C101.392 (3)C31—H310.93
C10—C111.374 (3)C32—C331.354 (4)
C10—H100.93C32—H320.93
C11—C121.376 (3)C33—C341.344 (4)
C11—H110.93C33—H330.93
C12—C131.362 (3)C34—C351.379 (3)
C12—H120.93C34—H340.93
C13—C141.392 (3)C35—H350.93
C30—Se1—C2997.90 (8)O4—C15—H15A109.1
N2—O2—C6109.86 (12)C6—C15—H15A109.1
C14—O4—C15115.61 (15)O4—C15—H15B109.1
C25—O5—C28117.78 (19)C6—C15—H15B109.1
C1—N1—C22133.82 (16)H15A—C15—H15B107.8
C1—N1—C395.27 (14)C17—C16—C21118.0 (2)
C22—N1—C3130.58 (16)C17—C16—C7123.1 (2)
O2—N2—C5105.81 (13)C21—C16—C7118.9 (2)
O2—N2—C4110.17 (14)C16—C17—C18120.8 (3)
C5—N2—C4108.50 (13)C16—C17—H17119.6
O1—C1—N1132.72 (18)C18—C17—H17119.6
O1—C1—C2135.53 (18)C19—C18—C17120.7 (3)
N1—C1—C291.72 (15)C19—C18—H18119.7
C4—C2—C1116.34 (16)C17—C18—H18119.7
C4—C2—C3106.57 (14)C18—C19—C20119.5 (3)
C1—C2—C385.72 (13)C18—C19—H19120.2
C4—C2—H2114.8C20—C19—H19120.2
C1—C2—H2114.8C19—C20—C21120.6 (3)
C3—C2—H2114.8C19—C20—H20119.7
N1—C3—C5117.72 (15)C21—C20—H20119.7
N1—C3—C287.24 (14)C20—C21—C16120.4 (3)
C5—C3—C2105.83 (14)C20—C21—H21119.8
N1—C3—H3114.2C16—C21—H21119.8
C5—C3—H3114.2C23—C22—C27119.77 (18)
C2—C3—H3114.2C23—C22—N1119.34 (17)
N2—C4—C29108.99 (15)C27—C22—N1120.88 (17)
N2—C4—C2101.55 (14)C22—C23—C24120.83 (19)
C29—C4—C2114.43 (15)C22—C23—H23119.6
N2—C4—H4110.5C24—C23—H23119.6
C29—C4—H4110.5C25—C24—C23119.5 (2)
C2—C4—H4110.5C25—C24—H24120.3
N2—C5—C7105.14 (15)C23—C24—H24120.3
N2—C5—C3102.61 (14)O5—C25—C24124.7 (2)
C7—C5—C3118.17 (15)O5—C25—C26115.79 (19)
N2—C5—H5110.1C24—C25—C26119.50 (19)
C7—C5—H5110.1C27—C26—C25121.1 (2)
C3—C5—H5110.1C27—C26—H26119.5
O2—C6—C15107.66 (14)C25—C26—H26119.5
O2—C6—C8104.47 (14)C26—C27—C22119.4 (2)
C15—C6—C8108.99 (15)C26—C27—H27120.3
O2—C6—C7106.06 (13)C22—C27—H27120.3
C15—C6—C7114.39 (15)O5—C28—H28A109.5
C8—C6—C7114.54 (14)O5—C28—H28B109.5
C16—C7—C5116.80 (16)H28A—C28—H28B109.5
C16—C7—C6115.20 (15)O5—C28—H28C109.5
C5—C7—C6101.63 (14)H28A—C28—H28C109.5
C16—C7—H7107.5H28B—C28—H28C109.5
C5—C7—H7107.5C4—C29—Se1110.03 (13)
C6—C7—H7107.5C4—C29—H29A109.7
O3—C8—C9122.98 (18)Se1—C29—H29A109.7
O3—C8—C6122.14 (17)C4—C29—H29B109.7
C9—C8—C6114.72 (15)Se1—C29—H29B109.7
C14—C9—C10118.95 (18)H29A—C29—H29B108.2
C14—C9—C8119.98 (18)C31—C30—C35118.4 (2)
C10—C9—C8120.96 (17)C31—C30—Se1122.08 (17)
C11—C10—C9120.5 (2)C35—C30—Se1119.48 (17)
C11—C10—H10119.7C30—C31—C32120.1 (2)
C9—C10—H10119.7C30—C31—H31119.9
C10—C11—C12119.6 (2)C32—C31—H31119.9
C10—C11—H11120.2C33—C32—C31120.4 (3)
C12—C11—H11120.2C33—C32—H32119.8
C13—C12—C11121.4 (2)C31—C32—H32119.8
C13—C12—H12119.3C34—C33—C32119.8 (2)
C11—C12—H12119.3C34—C33—H33120.1
C12—C13—C14119.5 (2)C32—C33—H33120.1
C12—C13—H13120.3C33—C34—C35120.9 (2)
C14—C13—H13120.3C33—C34—H34119.6
O4—C14—C9123.26 (17)C35—C34—H34119.6
O4—C14—C13116.63 (17)C30—C35—C34120.3 (2)
C9—C14—C13120.1 (2)C30—C35—H35119.8
O4—C15—C6112.56 (16)C34—C35—H35119.8
C6—O2—N2—C515.91 (18)C8—C9—C10—C11174.9 (2)
C6—O2—N2—C4−101.18 (16)C9—C10—C11—C120.3 (3)
C22—N1—C1—O1−6.5 (4)C10—C11—C12—C130.5 (4)
C3—N1—C1—O1179.8 (2)C11—C12—C13—C14−0.3 (4)
C22—N1—C1—C2175.33 (19)C15—O4—C14—C916.9 (3)
C3—N1—C1—C21.69 (14)C15—O4—C14—C13−163.62 (19)
O1—C1—C2—C4−73.3 (3)C10—C9—C14—O4−178.98 (18)
N1—C1—C2—C4104.78 (17)C8—C9—C14—O44.8 (3)
O1—C1—C2—C3−179.7 (2)C10—C9—C14—C131.5 (3)
N1—C1—C2—C3−1.60 (13)C8—C9—C14—C13−174.72 (19)
C1—N1—C3—C5−108.13 (18)C12—C13—C14—O4179.7 (2)
C22—N1—C3—C577.9 (2)C12—C13—C14—C9−0.7 (3)
C1—N1—C3—C2−1.67 (14)C14—O4—C15—C6−48.8 (2)
C22—N1—C3—C2−175.64 (18)O2—C6—C15—O4−55.5 (2)
C4—C2—C3—N1−114.74 (15)C8—C6—C15—O457.3 (2)
C1—C2—C3—N11.49 (12)C7—C6—C15—O4−173.07 (16)
C4—C2—C3—C53.32 (19)C5—C7—C16—C17−32.9 (3)
C1—C2—C3—C5119.55 (15)C6—C7—C16—C1786.3 (3)
O2—N2—C4—C29−84.46 (17)C5—C7—C16—C21147.02 (19)
C5—N2—C4—C29160.14 (15)C6—C7—C16—C21−93.8 (2)
O2—N2—C4—C2154.42 (13)C21—C16—C17—C18−0.5 (4)
C5—N2—C4—C239.02 (17)C7—C16—C17—C18179.5 (2)
C1—C2—C4—N2−118.02 (17)C16—C17—C18—C190.4 (5)
C3—C2—C4—N2−24.55 (18)C17—C18—C19—C200.0 (5)
C1—C2—C4—C29124.75 (19)C18—C19—C20—C21−0.3 (5)
C3—C2—C4—C29−141.78 (17)C19—C20—C21—C160.2 (4)
O2—N2—C5—C7−31.16 (17)C17—C16—C21—C200.1 (4)
C4—N2—C5—C787.05 (16)C7—C16—C21—C20−179.8 (2)
O2—N2—C5—C3−155.33 (14)C1—N1—C22—C23−160.4 (2)
C4—N2—C5—C3−37.13 (18)C3—N1—C22—C2311.3 (3)
N1—C3—C5—N2114.86 (17)C1—N1—C22—C2720.8 (3)
C2—C3—C5—N219.55 (18)C3—N1—C22—C27−167.57 (18)
N1—C3—C5—C7−0.2 (2)C27—C22—C23—C240.6 (3)
C2—C3—C5—C7−95.50 (18)N1—C22—C23—C24−178.19 (19)
N2—O2—C6—C15−117.18 (16)C22—C23—C24—C25−0.1 (3)
N2—O2—C6—C8127.06 (14)C28—O5—C25—C24−8.2 (3)
N2—O2—C6—C75.68 (18)C28—O5—C25—C26172.7 (2)
N2—C5—C7—C16159.75 (15)C23—C24—C25—O5−179.9 (2)
C3—C5—C7—C16−86.6 (2)C23—C24—C25—C26−0.8 (3)
N2—C5—C7—C633.51 (17)O5—C25—C26—C27−179.7 (2)
C3—C5—C7—C6147.19 (16)C24—C25—C26—C271.1 (3)
O2—C6—C7—C16−151.09 (16)C25—C26—C27—C22−0.6 (3)
C15—C6—C7—C16−32.6 (2)C23—C22—C27—C26−0.3 (3)
C8—C6—C7—C1694.2 (2)N1—C22—C27—C26178.50 (18)
O2—C6—C7—C5−23.81 (18)N2—C4—C29—Se1−174.50 (12)
C15—C6—C7—C594.68 (18)C2—C4—C29—Se1−61.6 (2)
C8—C6—C7—C5−138.47 (15)C30—Se1—C29—C4175.59 (15)
O2—C6—C8—O3−96.2 (2)C29—Se1—C30—C31−50.9 (2)
C15—C6—C8—O3148.92 (19)C29—Se1—C30—C35129.36 (18)
C7—C6—C8—O319.3 (3)C35—C30—C31—C32−0.3 (4)
O2—C6—C8—C979.28 (18)Se1—C30—C31—C32180.0 (2)
C15—C6—C8—C9−35.6 (2)C30—C31—C32—C331.0 (4)
C7—C6—C8—C9−165.14 (15)C31—C32—C33—C34−1.2 (5)
O3—C8—C9—C14−178.1 (2)C32—C33—C34—C350.6 (4)
C6—C8—C9—C146.5 (2)C31—C30—C35—C34−0.2 (3)
O3—C8—C9—C105.8 (3)Se1—C30—C35—C34179.50 (18)
C6—C8—C9—C10−169.71 (17)C33—C34—C35—C300.1 (4)
C14—C9—C10—C11−1.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.982.423.199 (3)136
C29—H29A···O5ii0.972.543.465 (3)160

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x+1/2, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2571).

References

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