organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146

[4-(4-Meth­­oxy­phen­yl)-8-oxo-3-(phenyl­selan­yl)spiro­[4.5]deca-3,6,9-trien-2-yl]methyl­cyanamide

aLife and Health Sciences Department, University of North Texas at Dallas, 7400 University Hills Blvd, Dallas, TX 75241, USA, and bDepartment of Chemistry and Biochemistry, University of Texas at Arlington, 701 S. Nedderman Dr., Arlington, TX 76019, USA
*Correspondence e-mail: myousuf@untdallas.edu

Edited by R. J. Butcher, Howard University, USA (Received 27 December 2019; accepted 22 January 2020; online 28 January 2020)

The title compound, C25H22N2O2Se, crystallizes in the space group P21/c with one mol­ecule in the asymmetric unit. The compound was synthesized by the addition of phenyl­selenyl bromide to a cyanamide. The phenyl­selenyl portion and the cyano group, as well as the ketone functional group in the cyclo­hexa-2,5-dien-1-one portion of the structure, are disordered, with occupancy factors of 0.555 (14) and 0.445 (14).

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Previously, our group reported the synthesis of a spiro­cyclization compound (Singh et al., 2016[Singh, R. P., Spears, J. A., Dalipe, A., Yousufuddin, M. & Lovely, C. J. (2016). Tetrahedron Lett. 57, 3096-3099.]) while attempting to form a cyanamide (Yousufuddin et al., 2018[Yousufuddin, M., Morales, R., Cassis, W., Brown, G. W., Singh, R. P. & Lovely, C. J. (2018). IUCrData, 3, x180389.]). We were able to show that the title compound could be synthesized by reacting the cyanamide with phenyl­selenyl bromide. We have since used spiro­cyclization of propargyl­amines (compounds that are related to cyanamides) to produce several thia­zolidines and thia­zolidones (Singh et al., 2019[Singh, R. P., Gout, D. & Lovely, C. J. (2019). Eur. J. Org. Chem. 2019, 1726-1740.]).

The title compound crystallizes in the monoclinic space group P21/c. There is one mol­ecule in the asymmetric unit yielding a Z value of 4 (Fig. 1[link]).

[Figure 1]
Figure 1
Molecular plot of title compound with ellipsoids drawn at 50% probability. Disordered portions are omitted for clarity.

The compound contains one phenyl­selanyl group that is disordered over two conformations, with occupancies of 0.555 (14) and 0.445 (14). The central five-membered ring is almost planar, with a maximum deviation for the C13 atom of only 0.133 (2) Å. In the spiro region of the mol­ecule, the dihedral angle between the central five-membered ring and the cyclo­hexa-2,5-dien-1-one unit is 88.22 (7)°. The dihedral angle between the central ring and the meth­oxy­phenyl group is only 55.98 (10)°, while the angle with the major component of the disordered phenyl­selanyl group is 88.6 (2)°. The Se1A atom is 1.883 (4) Å from C1 and 1.901 (7) Å from C18, while Se1B is 1.926 (5) Å from C1 and 1.920 (9) Å from C18. The C1—Se1A—C18 bond angle is 101.2 (4)° and the C1—Se1B—C18A bond angle is 98.2 (5)°.

Synthesis and crystallization

The title compound was synthesized and crystallized following the procedure reported by our group (Singh et al., 2016[Singh, R. P., Spears, J. A., Dalipe, A., Yousufuddin, M. & Lovely, C. J. (2016). Tetrahedron Lett. 57, 3096-3099.]).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link]. The refinement for the title compound indicated positional disorder at the phenyl ring attached to the Se atom and the cyano group as well as the ketone functional group in the cyclo­hexa-2,5-dien-1-one unit. These components were refined isotropically and the second component for each group was located in the resulting difference-Fourier map. The occupancies of these moieties were refined to a ratio of 0.555 (14):0.445 (14), with their anisotropic displacement parameters (ADP) treated with a combination of SIMU and DELU commands, which restrain the ADP values to be more reasonable.

Table 1
Experimental details

Crystal data
Chemical formula C25H22N2O2Se
Mr 461.40
Crystal system, space group Monoclinic, P21/c
Temperature (K) 296
a, b, c (Å) 13.209 (7), 6.343 (3), 27.080 (14)
β (°) 103.356 (8)
V3) 2207.4 (19)
Z 4
Radiation type Mo Kα
μ (mm−1) 1.72
Crystal size (mm) 0.70 × 0.18 × 0.10
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2016[Bruker (2016). APEX2, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA])
Tmin, Tmax 0.466, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections 22486, 5498, 3448
Rint 0.047
(sin θ/λ)max−1) 0.668
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.108, 1.03
No. of reflections 5498
No. of parameters 322
No. of restraints 222
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.34, −0.38
Computer programs: APEX2 and SAINT (Bruker, 2016[Bruker (2016). APEX2, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA]), SHELXT2014 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2018 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

[4-(4-Methoxyphenyl)-8-oxo-3-(phenylselanyl)spiro[4.5]deca-3,6,9-trien-2-yl]methylcyanamide top
Crystal data top
C25H22N2O2SeF(000) = 944
Mr = 461.40Dx = 1.388 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.209 (7) ÅCell parameters from 3960 reflections
b = 6.343 (3) Åθ = 2.5–22.7°
c = 27.080 (14) ŵ = 1.72 mm1
β = 103.356 (8)°T = 296 K
V = 2207.4 (19) Å3Needle, colourless
Z = 40.70 × 0.18 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
3448 reflections with I > 2σ(I)
φ and ω scansRint = 0.047
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 28.3°, θmin = 2.5°
Tmin = 0.466, Tmax = 0.745h = 1717
22486 measured reflectionsk = 88
5498 independent reflectionsl = 3536
Refinement top
Refinement on F2222 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.108 w = 1/[σ2(Fo2) + (0.044P)2 + 0.3647P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5498 reflectionsΔρmax = 0.34 e Å3
322 parametersΔρmin = 0.38 e Å3
Special details top

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

Refinement. The H atoms were included in calculated positions and refined using a riding model, with C—H = 0.93, 0.96, 0.97, and 0.98 Å for aromatic, methyl, methylene, and terminal H atoms, respectively, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(C-methyl).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Se1A0.6308 (3)0.4941 (10)0.26771 (16)0.0642 (7)0.555 (14)
Se1B0.6377 (4)0.5228 (12)0.2657 (2)0.0694 (9)0.445 (14)
O10.43190 (15)1.1265 (3)0.40821 (9)0.0857 (6)
O2A0.868 (2)0.680 (5)0.5648 (13)0.090 (4)0.555 (14)
O2B0.884 (3)0.623 (6)0.5682 (15)0.098 (6)0.445 (14)
N10.90074 (14)0.4281 (3)0.31172 (8)0.0486 (5)
N20.9080 (2)0.8146 (4)0.31572 (12)0.0968 (10)
C10.72698 (16)0.4392 (3)0.32939 (9)0.0433 (5)
C20.82397 (16)0.3120 (3)0.33276 (8)0.0429 (5)
H20.8063140.1797350.3140560.051*
C30.85901 (19)0.2646 (4)0.38949 (9)0.0529 (6)
H3A0.9341440.2742770.4004990.063*
H3B0.8378730.1234900.3966110.063*
C40.80622 (18)0.4317 (4)0.41768 (9)0.0482 (6)
C50.71565 (17)0.5081 (3)0.37431 (9)0.0440 (5)
C60.63660 (17)0.6620 (4)0.38302 (8)0.0459 (5)
C70.62917 (18)0.8586 (4)0.35983 (9)0.0543 (6)
H70.6722340.8901910.3380880.065*
C80.5593 (2)1.0078 (4)0.36838 (12)0.0620 (7)
H80.5548821.1381080.3522780.074*
C90.4961 (2)0.9627 (4)0.40089 (11)0.0582 (7)
C100.49946 (19)0.7697 (4)0.42348 (9)0.0602 (7)
H100.4552690.7391090.4447340.072*
C110.56992 (19)0.6186 (4)0.41439 (9)0.0555 (6)
H110.5720890.4867860.4296380.067*
C120.3628 (3)1.0895 (6)0.44033 (13)0.0939 (10)
H12D0.3133420.9830740.4255670.141*
H12E0.3266691.2176220.4441980.141*
H12F0.4015541.0428670.4729580.141*
C130.7701 (2)0.3312 (4)0.46039 (10)0.0599 (7)
H130.7281240.2121310.4532760.072*
C140.7940 (2)0.4009 (5)0.50789 (10)0.0708 (8)
H140.7699860.3269850.5325720.085*
C150.8565 (2)0.5889 (6)0.52255 (11)0.0713 (8)
C160.8959 (2)0.6902 (4)0.48293 (10)0.0628 (7)
H160.9374620.8094460.4908640.075*
C170.87484 (18)0.6182 (4)0.43561 (9)0.0532 (6)
H170.9043690.6876370.4121350.064*
C180.6898 (7)0.3385 (11)0.2213 (4)0.0502 (15)0.555 (14)
C190.6434 (6)0.1406 (12)0.2145 (3)0.0605 (15)0.555 (14)
H19A0.5925570.1049610.2317100.073*0.555 (14)
C200.6731 (7)0.0041 (8)0.1819 (3)0.0690 (16)0.555 (14)
H20A0.6421340.1364670.1773920.083*0.555 (14)
C210.7492 (6)0.0492 (13)0.1562 (2)0.0632 (17)0.555 (14)
H21A0.7690560.0475860.1344380.076*0.555 (14)
C220.7955 (5)0.2471 (15)0.1630 (3)0.0640 (16)0.555 (14)
H22A0.8464020.2827250.1458030.077*0.555 (14)
C230.7658 (7)0.3917 (11)0.1956 (3)0.0584 (14)0.555 (14)
H23A0.7968270.5241560.2001210.070*0.555 (14)
C18A0.6849 (10)0.3222 (15)0.2228 (5)0.0531 (18)0.445 (14)
C19A0.6599 (8)0.1141 (15)0.2091 (4)0.0598 (17)0.445 (14)
H19B0.6122250.0417990.2232140.072*0.445 (14)
C20A0.7062 (8)0.0142 (10)0.1743 (4)0.0644 (19)0.445 (14)
H20B0.6894980.1250070.1650740.077*0.445 (14)
C21A0.7775 (7)0.1223 (17)0.1532 (3)0.0627 (19)0.445 (14)
H21B0.8084630.0554770.1298460.075*0.445 (14)
C22A0.8025 (6)0.3304 (18)0.1669 (4)0.0675 (18)0.445 (14)
H22B0.8501570.4027670.1527570.081*0.445 (14)
C23A0.7562 (9)0.4304 (12)0.2017 (5)0.0629 (18)0.445 (14)
H23B0.7728850.5695770.2108960.076*0.445 (14)
C240.9049 (2)0.6355 (4)0.31394 (10)0.0572 (6)
C250.9865 (2)0.3112 (4)0.29936 (11)0.0645 (7)
H25A1.0264220.4036480.2831480.097*
H25B0.9593570.1972600.2768550.097*
H25C1.0301960.2557830.3299270.097*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se1A0.0461 (8)0.0904 (17)0.0530 (12)0.0220 (7)0.0050 (6)0.0105 (10)
Se1B0.081 (2)0.0812 (14)0.0464 (10)0.0381 (14)0.0162 (11)0.0066 (9)
O10.0773 (14)0.0701 (13)0.1199 (17)0.0161 (11)0.0439 (13)0.0128 (12)
O2A0.075 (7)0.140 (10)0.057 (4)0.008 (5)0.018 (4)0.023 (6)
O2B0.072 (10)0.170 (19)0.055 (7)0.012 (11)0.021 (7)0.039 (11)
N10.0476 (11)0.0361 (10)0.0676 (13)0.0036 (8)0.0250 (10)0.0006 (9)
N20.131 (2)0.0393 (14)0.149 (3)0.0025 (13)0.092 (2)0.0027 (15)
C10.0399 (12)0.0427 (12)0.0487 (13)0.0004 (9)0.0134 (10)0.0010 (10)
C20.0422 (12)0.0379 (12)0.0502 (13)0.0003 (9)0.0142 (10)0.0010 (10)
C30.0530 (14)0.0495 (14)0.0560 (14)0.0052 (11)0.0124 (11)0.0039 (11)
C40.0495 (14)0.0508 (13)0.0455 (13)0.0051 (11)0.0136 (10)0.0041 (11)
C50.0399 (11)0.0464 (13)0.0482 (12)0.0028 (10)0.0149 (10)0.0007 (11)
C60.0435 (13)0.0499 (13)0.0455 (12)0.0042 (10)0.0125 (10)0.0078 (11)
C70.0504 (14)0.0523 (15)0.0638 (15)0.0046 (11)0.0205 (12)0.0046 (12)
C80.0603 (16)0.0481 (15)0.0793 (19)0.0019 (12)0.0196 (14)0.0024 (13)
C90.0516 (15)0.0561 (16)0.0687 (17)0.0022 (12)0.0180 (13)0.0166 (13)
C100.0517 (15)0.0740 (18)0.0607 (16)0.0035 (13)0.0248 (12)0.0078 (14)
C110.0563 (15)0.0571 (15)0.0568 (15)0.0006 (12)0.0208 (12)0.0024 (12)
C120.072 (2)0.116 (3)0.101 (3)0.024 (2)0.0358 (19)0.025 (2)
C130.0585 (16)0.0653 (16)0.0566 (16)0.0089 (13)0.0145 (12)0.0097 (13)
C140.0679 (18)0.099 (2)0.0490 (16)0.0049 (17)0.0210 (13)0.0127 (16)
C150.0529 (16)0.108 (2)0.0532 (17)0.0005 (16)0.0122 (13)0.0099 (17)
C160.0529 (15)0.0700 (17)0.0645 (17)0.0075 (13)0.0120 (12)0.0131 (14)
C170.0487 (14)0.0558 (15)0.0551 (15)0.0056 (11)0.0119 (11)0.0018 (12)
C180.045 (3)0.064 (3)0.041 (3)0.008 (3)0.009 (2)0.003 (3)
C190.059 (3)0.070 (3)0.054 (3)0.011 (3)0.017 (2)0.004 (3)
C200.068 (4)0.080 (3)0.061 (3)0.009 (3)0.018 (3)0.009 (3)
C210.066 (4)0.074 (4)0.053 (3)0.008 (3)0.021 (3)0.006 (3)
C220.066 (3)0.075 (4)0.054 (3)0.014 (3)0.020 (2)0.011 (3)
C230.057 (3)0.075 (3)0.049 (3)0.007 (3)0.025 (2)0.003 (3)
C18A0.051 (3)0.063 (3)0.044 (3)0.010 (3)0.009 (3)0.001 (3)
C19A0.063 (3)0.064 (3)0.055 (3)0.008 (3)0.018 (3)0.007 (3)
C20A0.070 (4)0.071 (3)0.055 (3)0.010 (3)0.021 (3)0.007 (3)
C21A0.066 (4)0.070 (4)0.054 (3)0.009 (3)0.018 (3)0.008 (3)
C22A0.073 (3)0.076 (4)0.057 (3)0.008 (3)0.020 (3)0.009 (4)
C23A0.062 (3)0.076 (3)0.054 (3)0.014 (3)0.019 (3)0.008 (3)
C240.0641 (16)0.0477 (16)0.0697 (17)0.0007 (12)0.0362 (13)0.0036 (12)
C250.0585 (16)0.0543 (15)0.091 (2)0.0049 (12)0.0378 (14)0.0049 (14)
Geometric parameters (Å, º) top
Se1A—C11.883 (4)C12—H12F0.9600
Se1A—C181.901 (6)C13—C141.328 (4)
Se1B—C18A1.921 (9)C13—H130.9300
Se1B—C11.926 (5)C14—C151.452 (4)
O1—C91.384 (3)C14—H140.9300
O1—C121.418 (4)C15—C161.447 (4)
O2A—C151.26 (3)C16—C171.328 (3)
O2B—C151.22 (4)C16—H160.9300
N1—C241.318 (3)C17—H170.9300
N1—C251.456 (3)C18—C191.3900
N1—C21.470 (3)C18—C231.3900
N2—C241.137 (3)C19—C201.3900
C1—C51.333 (3)C19—H19A0.9300
C1—C21.499 (3)C20—C211.3900
C2—C31.528 (3)C20—H20A0.9300
C2—H20.9800C21—C221.3900
C3—C41.562 (3)C21—H21A0.9300
C3—H3A0.9700C22—C231.3900
C3—H3B0.9700C22—H22A0.9300
C4—C131.492 (3)C23—H23A0.9300
C4—C171.501 (3)C18A—C19A1.3900
C4—C51.548 (3)C18A—C23A1.3900
C5—C61.488 (3)C19A—C20A1.3900
C6—C111.385 (3)C19A—H19B0.9300
C6—C71.389 (3)C20A—C21A1.3900
C7—C81.378 (3)C20A—H20B0.9300
C7—H70.9300C21A—C22A1.3900
C8—C91.376 (4)C21A—H21B0.9300
C8—H80.9300C22A—C23A1.3900
C9—C101.364 (4)C22A—H22B0.9300
C10—C111.397 (3)C23A—H23B0.9300
C10—H100.9300C25—H25A0.9600
C11—H110.9300C25—H25B0.9600
C12—H12D0.9600C25—H25C0.9600
C12—H12E0.9600
C1—Se1A—C18101.2 (4)C4—C13—H13117.9
C18A—Se1B—C198.1 (5)C13—C14—C15122.1 (3)
C9—O1—C12117.8 (2)C13—C14—H14119.0
C24—N1—C25119.50 (19)C15—C14—H14119.0
C24—N1—C2120.49 (18)O2B—C15—C16127 (2)
C25—N1—C2118.50 (18)O2A—C15—C16118.7 (17)
C5—C1—C2113.3 (2)O2B—C15—C14116 (2)
C5—C1—Se1A123.6 (2)O2A—C15—C14124.6 (17)
C2—C1—Se1A123.1 (2)C16—C15—C14116.2 (2)
C5—C1—Se1B123.5 (3)C17—C16—C15122.1 (3)
C2—C1—Se1B122.7 (2)C17—C16—H16118.9
N1—C2—C1111.31 (17)C15—C16—H16118.9
N1—C2—C3114.34 (18)C16—C17—C4124.0 (2)
C1—C2—C3102.90 (17)C16—C17—H17118.0
N1—C2—H2109.4C4—C17—H17118.0
C1—C2—H2109.4C19—C18—C23120.0
C3—C2—H2109.4C19—C18—Se1A108.8 (5)
C2—C3—C4106.98 (18)C23—C18—Se1A131.2 (5)
C2—C3—H3A110.3C20—C19—C18120.0
C4—C3—H3A110.3C20—C19—H19A120.0
C2—C3—H3B110.3C18—C19—H19A120.0
C4—C3—H3B110.3C19—C20—C21120.0
H3A—C3—H3B108.6C19—C20—H20A120.0
C13—C4—C17111.3 (2)C21—C20—H20A120.0
C13—C4—C5113.1 (2)C20—C21—C22120.0
C17—C4—C5107.56 (19)C20—C21—H21A120.0
C13—C4—C3110.4 (2)C22—C21—H21A120.0
C17—C4—C3112.87 (19)C23—C22—C21120.0
C5—C4—C3101.28 (18)C23—C22—H22A120.0
C1—C5—C6126.2 (2)C21—C22—H22A120.0
C1—C5—C4111.1 (2)C22—C23—C18120.0
C6—C5—C4122.2 (2)C22—C23—H23A120.0
C11—C6—C7117.8 (2)C18—C23—H23A120.0
C11—C6—C5122.4 (2)C19A—C18A—C23A120.0
C7—C6—C5119.7 (2)C19A—C18A—Se1B134.5 (7)
C8—C7—C6121.3 (2)C23A—C18A—Se1B105.5 (7)
C8—C7—H7119.3C20A—C19A—C18A120.0
C6—C7—H7119.3C20A—C19A—H19B120.0
C9—C8—C7119.6 (2)C18A—C19A—H19B120.0
C9—C8—H8120.2C21A—C20A—C19A120.0
C7—C8—H8120.2C21A—C20A—H20B120.0
C10—C9—C8120.8 (2)C19A—C20A—H20B120.0
C10—C9—O1124.5 (2)C20A—C21A—C22A120.0
C8—C9—O1114.7 (2)C20A—C21A—H21B120.0
C9—C10—C11119.4 (2)C22A—C21A—H21B120.0
C9—C10—H10120.3C21A—C22A—C23A120.0
C11—C10—H10120.3C21A—C22A—H22B120.0
C6—C11—C10121.0 (2)C23A—C22A—H22B120.0
C6—C11—H11119.5C22A—C23A—C18A120.0
C10—C11—H11119.5C22A—C23A—H23B120.0
O1—C12—H12D109.5C18A—C23A—H23B120.0
O1—C12—H12E109.5N2—C24—N1179.7 (4)
H12D—C12—H12E109.5N1—C25—H25A109.5
O1—C12—H12F109.5N1—C25—H25B109.5
H12D—C12—H12F109.5H25A—C25—H25B109.5
H12E—C12—H12F109.5N1—C25—H25C109.5
C14—C13—C4124.2 (3)H25A—C25—H25C109.5
C14—C13—H13117.9H25B—C25—H25C109.5
C18—Se1A—C1—C5176.5 (3)C12—O1—C9—C101.8 (4)
C18—Se1A—C1—C23.1 (5)C12—O1—C9—C8178.5 (3)
C24—N1—C2—C130.3 (3)C8—C9—C10—C111.6 (4)
C25—N1—C2—C1163.8 (2)O1—C9—C10—C11178.0 (2)
C24—N1—C2—C385.8 (3)C7—C6—C11—C101.7 (4)
C25—N1—C2—C380.2 (3)C5—C6—C11—C10177.3 (2)
C5—C1—C2—N1109.0 (2)C9—C10—C11—C60.3 (4)
Se1A—C1—C2—N171.3 (3)C17—C4—C13—C141.3 (4)
Se1B—C1—C2—N163.7 (4)C5—C4—C13—C14119.9 (3)
C5—C1—C2—C313.9 (2)C3—C4—C13—C14127.4 (3)
Se1A—C1—C2—C3165.8 (3)C4—C13—C14—C151.8 (5)
Se1B—C1—C2—C3173.4 (3)C13—C14—C15—O2B171.4 (16)
N1—C2—C3—C4100.3 (2)C13—C14—C15—O2A168.6 (13)
C1—C2—C3—C420.6 (2)C13—C14—C15—C163.2 (4)
C2—C3—C4—C13139.8 (2)O2B—C15—C16—C17168.1 (17)
C2—C3—C4—C1795.0 (2)O2A—C15—C16—C17171.0 (13)
C2—C3—C4—C519.7 (2)C14—C15—C16—C171.3 (4)
C2—C1—C5—C6170.7 (2)C15—C16—C17—C42.0 (4)
Se1A—C1—C5—C69.6 (4)C13—C4—C17—C163.2 (3)
Se1B—C1—C5—C61.9 (4)C5—C4—C17—C16121.2 (3)
C2—C1—C5—C41.2 (3)C3—C4—C17—C16128.0 (3)
Se1A—C1—C5—C4178.5 (3)C23—C18—C19—C200.0
Se1B—C1—C5—C4173.9 (3)Se1A—C18—C19—C20179.8 (7)
C13—C4—C5—C1129.8 (2)C18—C19—C20—C210.0
C17—C4—C5—C1106.9 (2)C19—C20—C21—C220.0
C3—C4—C5—C111.7 (2)C20—C21—C22—C230.0
C13—C4—C5—C657.9 (3)C21—C22—C23—C180.0
C17—C4—C5—C665.4 (3)C19—C18—C23—C220.0
C3—C4—C5—C6175.99 (19)Se1A—C18—C23—C22179.8 (8)
C1—C5—C6—C11125.9 (3)C23A—C18A—C19A—C20A0.0
C4—C5—C6—C1163.1 (3)Se1B—C18A—C19A—C20A176.7 (11)
C1—C5—C6—C755.1 (3)C18A—C19A—C20A—C21A0.0
C4—C5—C6—C7115.9 (2)C19A—C20A—C21A—C22A0.0
C11—C6—C7—C81.2 (4)C20A—C21A—C22A—C23A0.0
C5—C6—C7—C8177.8 (2)C21A—C22A—C23A—C18A0.0
C6—C7—C8—C90.6 (4)C19A—C18A—C23A—C22A0.0
C7—C8—C9—C102.1 (4)Se1B—C18A—C23A—C22A177.6 (8)
C7—C8—C9—O1177.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N2i0.982.673.411 (4)132
C3—H3A···O2Aii0.972.583.55 (3)176
C3—H3A···O2Bii0.972.443.40 (4)168
C12—H12E···O2Aiii0.962.613.36 (3)135
C19—H19A···Se1Aiv0.933.043.876 (8)151
Symmetry codes: (i) x, y1, z; (ii) x+2, y+1, z+1; (iii) x+1, y+2, z+1; (iv) x+1, y1/2, z+1/2.
 

Funding information

Funding for this research was provided by: Robert A. Welch Foundation (grant No. 4-1362).

References

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