organic compounds
[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
The title compound, C25H22N2O2Se, crystallizes in the P21/c with one molecule in the 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 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).
Keywords: crystal structure; cyanamide; propargylamines; spiro compounds; phenylselanyl derivatives.
CCDC reference: 1979402
Structure description
Previously, our group reported the synthesis of a spirocyclization compound (Singh et al., 2016) while attempting to form a cyanamide (Yousufuddin et al., 2018). 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).
The title compound crystallizes in the monoclinic P21/c. There is one molecule in the yielding a Z value of 4 (Fig. 1).
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).
Refinement
Crystal data, data collection and structure . The 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 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.
details are summarized in Table 1Structural data
CCDC reference: 1979402
https://doi.org/10.1107/S2414314620000784/bv4028sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620000784/bv4028Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314620000784/bv4028Isup3.cml
Data collection: APEX2 (Bruker, 2016); cell
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).C25H22N2O2Se | F(000) = 944 |
Mr = 461.40 | Dx = 1.388 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.209 (7) Å | Cell parameters from 3960 reflections |
b = 6.343 (3) Å | θ = 2.5–22.7° |
c = 27.080 (14) Å | µ = 1.72 mm−1 |
β = 103.356 (8)° | T = 296 K |
V = 2207.4 (19) Å3 | Needle, colourless |
Z = 4 | 0.70 × 0.18 × 0.10 mm |
Bruker APEXII CCD diffractometer | 3448 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.047 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 28.3°, θmin = 2.5° |
Tmin = 0.466, Tmax = 0.745 | h = −17→17 |
22486 measured reflections | k = −8→8 |
5498 independent reflections | l = −35→36 |
Refinement on F2 | 222 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-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 reflections | Δρmax = 0.34 e Å−3 |
322 parameters | Δρmin = −0.38 e Å−3 |
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). |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Se1A | 0.6308 (3) | 0.4941 (10) | 0.26771 (16) | 0.0642 (7) | 0.555 (14) |
Se1B | 0.6377 (4) | 0.5228 (12) | 0.2657 (2) | 0.0694 (9) | 0.445 (14) |
O1 | 0.43190 (15) | 1.1265 (3) | 0.40821 (9) | 0.0857 (6) | |
O2A | 0.868 (2) | 0.680 (5) | 0.5648 (13) | 0.090 (4) | 0.555 (14) |
O2B | 0.884 (3) | 0.623 (6) | 0.5682 (15) | 0.098 (6) | 0.445 (14) |
N1 | 0.90074 (14) | 0.4281 (3) | 0.31172 (8) | 0.0486 (5) | |
N2 | 0.9080 (2) | 0.8146 (4) | 0.31572 (12) | 0.0968 (10) | |
C1 | 0.72698 (16) | 0.4392 (3) | 0.32939 (9) | 0.0433 (5) | |
C2 | 0.82397 (16) | 0.3120 (3) | 0.33276 (8) | 0.0429 (5) | |
H2 | 0.806314 | 0.179735 | 0.314056 | 0.051* | |
C3 | 0.85901 (19) | 0.2646 (4) | 0.38949 (9) | 0.0529 (6) | |
H3A | 0.934144 | 0.274277 | 0.400499 | 0.063* | |
H3B | 0.837873 | 0.123490 | 0.396611 | 0.063* | |
C4 | 0.80622 (18) | 0.4317 (4) | 0.41768 (9) | 0.0482 (6) | |
C5 | 0.71565 (17) | 0.5081 (3) | 0.37431 (9) | 0.0440 (5) | |
C6 | 0.63660 (17) | 0.6620 (4) | 0.38302 (8) | 0.0459 (5) | |
C7 | 0.62917 (18) | 0.8586 (4) | 0.35983 (9) | 0.0543 (6) | |
H7 | 0.672234 | 0.890191 | 0.338088 | 0.065* | |
C8 | 0.5593 (2) | 1.0078 (4) | 0.36838 (12) | 0.0620 (7) | |
H8 | 0.554882 | 1.138108 | 0.352278 | 0.074* | |
C9 | 0.4961 (2) | 0.9627 (4) | 0.40089 (11) | 0.0582 (7) | |
C10 | 0.49946 (19) | 0.7697 (4) | 0.42348 (9) | 0.0602 (7) | |
H10 | 0.455269 | 0.739109 | 0.444734 | 0.072* | |
C11 | 0.56992 (19) | 0.6186 (4) | 0.41439 (9) | 0.0555 (6) | |
H11 | 0.572089 | 0.486786 | 0.429638 | 0.067* | |
C12 | 0.3628 (3) | 1.0895 (6) | 0.44033 (13) | 0.0939 (10) | |
H12D | 0.313342 | 0.983074 | 0.425567 | 0.141* | |
H12E | 0.326669 | 1.217622 | 0.444198 | 0.141* | |
H12F | 0.401554 | 1.042867 | 0.472958 | 0.141* | |
C13 | 0.7701 (2) | 0.3312 (4) | 0.46039 (10) | 0.0599 (7) | |
H13 | 0.728124 | 0.212131 | 0.453276 | 0.072* | |
C14 | 0.7940 (2) | 0.4009 (5) | 0.50789 (10) | 0.0708 (8) | |
H14 | 0.769986 | 0.326985 | 0.532572 | 0.085* | |
C15 | 0.8565 (2) | 0.5889 (6) | 0.52255 (11) | 0.0713 (8) | |
C16 | 0.8959 (2) | 0.6902 (4) | 0.48293 (10) | 0.0628 (7) | |
H16 | 0.937462 | 0.809446 | 0.490864 | 0.075* | |
C17 | 0.87484 (18) | 0.6182 (4) | 0.43561 (9) | 0.0532 (6) | |
H17 | 0.904369 | 0.687637 | 0.412135 | 0.064* | |
C18 | 0.6898 (7) | 0.3385 (11) | 0.2213 (4) | 0.0502 (15) | 0.555 (14) |
C19 | 0.6434 (6) | 0.1406 (12) | 0.2145 (3) | 0.0605 (15) | 0.555 (14) |
H19A | 0.592557 | 0.104961 | 0.231710 | 0.073* | 0.555 (14) |
C20 | 0.6731 (7) | −0.0041 (8) | 0.1819 (3) | 0.0690 (16) | 0.555 (14) |
H20A | 0.642134 | −0.136467 | 0.177392 | 0.083* | 0.555 (14) |
C21 | 0.7492 (6) | 0.0492 (13) | 0.1562 (2) | 0.0632 (17) | 0.555 (14) |
H21A | 0.769056 | −0.047586 | 0.134438 | 0.076* | 0.555 (14) |
C22 | 0.7955 (5) | 0.2471 (15) | 0.1630 (3) | 0.0640 (16) | 0.555 (14) |
H22A | 0.846402 | 0.282725 | 0.145803 | 0.077* | 0.555 (14) |
C23 | 0.7658 (7) | 0.3917 (11) | 0.1956 (3) | 0.0584 (14) | 0.555 (14) |
H23A | 0.796827 | 0.524156 | 0.200121 | 0.070* | 0.555 (14) |
C18A | 0.6849 (10) | 0.3222 (15) | 0.2228 (5) | 0.0531 (18) | 0.445 (14) |
C19A | 0.6599 (8) | 0.1141 (15) | 0.2091 (4) | 0.0598 (17) | 0.445 (14) |
H19B | 0.612225 | 0.041799 | 0.223214 | 0.072* | 0.445 (14) |
C20A | 0.7062 (8) | 0.0142 (10) | 0.1743 (4) | 0.0644 (19) | 0.445 (14) |
H20B | 0.689498 | −0.125007 | 0.165074 | 0.077* | 0.445 (14) |
C21A | 0.7775 (7) | 0.1223 (17) | 0.1532 (3) | 0.0627 (19) | 0.445 (14) |
H21B | 0.808463 | 0.055477 | 0.129846 | 0.075* | 0.445 (14) |
C22A | 0.8025 (6) | 0.3304 (18) | 0.1669 (4) | 0.0675 (18) | 0.445 (14) |
H22B | 0.850157 | 0.402767 | 0.152757 | 0.081* | 0.445 (14) |
C23A | 0.7562 (9) | 0.4304 (12) | 0.2017 (5) | 0.0629 (18) | 0.445 (14) |
H23B | 0.772885 | 0.569577 | 0.210896 | 0.076* | 0.445 (14) |
C24 | 0.9049 (2) | 0.6355 (4) | 0.31394 (10) | 0.0572 (6) | |
C25 | 0.9865 (2) | 0.3112 (4) | 0.29936 (11) | 0.0645 (7) | |
H25A | 1.026422 | 0.403648 | 0.283148 | 0.097* | |
H25B | 0.959357 | 0.197260 | 0.276855 | 0.097* | |
H25C | 1.030196 | 0.255783 | 0.329927 | 0.097* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1A | 0.0461 (8) | 0.0904 (17) | 0.0530 (12) | 0.0220 (7) | 0.0050 (6) | −0.0105 (10) |
Se1B | 0.081 (2) | 0.0812 (14) | 0.0464 (10) | 0.0381 (14) | 0.0162 (11) | 0.0066 (9) |
O1 | 0.0773 (14) | 0.0701 (13) | 0.1199 (17) | 0.0161 (11) | 0.0439 (13) | −0.0128 (12) |
O2A | 0.075 (7) | 0.140 (10) | 0.057 (4) | 0.008 (5) | 0.018 (4) | −0.023 (6) |
O2B | 0.072 (10) | 0.170 (19) | 0.055 (7) | −0.012 (11) | 0.021 (7) | −0.039 (11) |
N1 | 0.0476 (11) | 0.0361 (10) | 0.0676 (13) | 0.0036 (8) | 0.0250 (10) | −0.0006 (9) |
N2 | 0.131 (2) | 0.0393 (14) | 0.149 (3) | −0.0025 (13) | 0.092 (2) | 0.0027 (15) |
C1 | 0.0399 (12) | 0.0427 (12) | 0.0487 (13) | 0.0004 (9) | 0.0134 (10) | 0.0010 (10) |
C2 | 0.0422 (12) | 0.0379 (12) | 0.0502 (13) | 0.0003 (9) | 0.0142 (10) | 0.0010 (10) |
C3 | 0.0530 (14) | 0.0495 (14) | 0.0560 (14) | 0.0052 (11) | 0.0124 (11) | 0.0039 (11) |
C4 | 0.0495 (14) | 0.0508 (13) | 0.0455 (13) | −0.0051 (11) | 0.0136 (10) | 0.0041 (11) |
C5 | 0.0399 (11) | 0.0464 (13) | 0.0482 (12) | −0.0028 (10) | 0.0149 (10) | −0.0007 (11) |
C6 | 0.0435 (13) | 0.0499 (13) | 0.0455 (12) | −0.0042 (10) | 0.0125 (10) | −0.0078 (11) |
C7 | 0.0504 (14) | 0.0523 (15) | 0.0638 (15) | −0.0046 (11) | 0.0205 (12) | −0.0046 (12) |
C8 | 0.0603 (16) | 0.0481 (15) | 0.0793 (19) | −0.0019 (12) | 0.0196 (14) | −0.0024 (13) |
C9 | 0.0516 (15) | 0.0561 (16) | 0.0687 (17) | −0.0022 (12) | 0.0180 (13) | −0.0166 (13) |
C10 | 0.0517 (15) | 0.0740 (18) | 0.0607 (16) | −0.0035 (13) | 0.0248 (12) | −0.0078 (14) |
C11 | 0.0563 (15) | 0.0571 (15) | 0.0568 (15) | −0.0006 (12) | 0.0208 (12) | −0.0024 (12) |
C12 | 0.072 (2) | 0.116 (3) | 0.101 (3) | 0.024 (2) | 0.0358 (19) | −0.025 (2) |
C13 | 0.0585 (16) | 0.0653 (16) | 0.0566 (16) | −0.0089 (13) | 0.0145 (12) | 0.0097 (13) |
C14 | 0.0679 (18) | 0.099 (2) | 0.0490 (16) | −0.0049 (17) | 0.0210 (13) | 0.0127 (16) |
C15 | 0.0529 (16) | 0.108 (2) | 0.0532 (17) | 0.0005 (16) | 0.0122 (13) | −0.0099 (17) |
C16 | 0.0529 (15) | 0.0700 (17) | 0.0645 (17) | −0.0075 (13) | 0.0120 (12) | −0.0131 (14) |
C17 | 0.0487 (14) | 0.0558 (15) | 0.0551 (15) | −0.0056 (11) | 0.0119 (11) | 0.0018 (12) |
C18 | 0.045 (3) | 0.064 (3) | 0.041 (3) | 0.008 (3) | 0.009 (2) | 0.003 (3) |
C19 | 0.059 (3) | 0.070 (3) | 0.054 (3) | 0.011 (3) | 0.017 (2) | −0.004 (3) |
C20 | 0.068 (4) | 0.080 (3) | 0.061 (3) | 0.009 (3) | 0.018 (3) | −0.009 (3) |
C21 | 0.066 (4) | 0.074 (4) | 0.053 (3) | 0.008 (3) | 0.021 (3) | −0.006 (3) |
C22 | 0.066 (3) | 0.075 (4) | 0.054 (3) | 0.014 (3) | 0.020 (2) | −0.011 (3) |
C23 | 0.057 (3) | 0.075 (3) | 0.049 (3) | 0.007 (3) | 0.025 (2) | −0.003 (3) |
C18A | 0.051 (3) | 0.063 (3) | 0.044 (3) | 0.010 (3) | 0.009 (3) | −0.001 (3) |
C19A | 0.063 (3) | 0.064 (3) | 0.055 (3) | 0.008 (3) | 0.018 (3) | −0.007 (3) |
C20A | 0.070 (4) | 0.071 (3) | 0.055 (3) | 0.010 (3) | 0.021 (3) | −0.007 (3) |
C21A | 0.066 (4) | 0.070 (4) | 0.054 (3) | 0.009 (3) | 0.018 (3) | −0.008 (3) |
C22A | 0.073 (3) | 0.076 (4) | 0.057 (3) | 0.008 (3) | 0.020 (3) | −0.009 (4) |
C23A | 0.062 (3) | 0.076 (3) | 0.054 (3) | 0.014 (3) | 0.019 (3) | −0.008 (3) |
C24 | 0.0641 (16) | 0.0477 (16) | 0.0697 (17) | 0.0007 (12) | 0.0362 (13) | 0.0036 (12) |
C25 | 0.0585 (16) | 0.0543 (15) | 0.091 (2) | 0.0049 (12) | 0.0378 (14) | −0.0049 (14) |
Se1A—C1 | 1.883 (4) | C12—H12F | 0.9600 |
Se1A—C18 | 1.901 (6) | C13—C14 | 1.328 (4) |
Se1B—C18A | 1.921 (9) | C13—H13 | 0.9300 |
Se1B—C1 | 1.926 (5) | C14—C15 | 1.452 (4) |
O1—C9 | 1.384 (3) | C14—H14 | 0.9300 |
O1—C12 | 1.418 (4) | C15—C16 | 1.447 (4) |
O2A—C15 | 1.26 (3) | C16—C17 | 1.328 (3) |
O2B—C15 | 1.22 (4) | C16—H16 | 0.9300 |
N1—C24 | 1.318 (3) | C17—H17 | 0.9300 |
N1—C25 | 1.456 (3) | C18—C19 | 1.3900 |
N1—C2 | 1.470 (3) | C18—C23 | 1.3900 |
N2—C24 | 1.137 (3) | C19—C20 | 1.3900 |
C1—C5 | 1.333 (3) | C19—H19A | 0.9300 |
C1—C2 | 1.499 (3) | C20—C21 | 1.3900 |
C2—C3 | 1.528 (3) | C20—H20A | 0.9300 |
C2—H2 | 0.9800 | C21—C22 | 1.3900 |
C3—C4 | 1.562 (3) | C21—H21A | 0.9300 |
C3—H3A | 0.9700 | C22—C23 | 1.3900 |
C3—H3B | 0.9700 | C22—H22A | 0.9300 |
C4—C13 | 1.492 (3) | C23—H23A | 0.9300 |
C4—C17 | 1.501 (3) | C18A—C19A | 1.3900 |
C4—C5 | 1.548 (3) | C18A—C23A | 1.3900 |
C5—C6 | 1.488 (3) | C19A—C20A | 1.3900 |
C6—C11 | 1.385 (3) | C19A—H19B | 0.9300 |
C6—C7 | 1.389 (3) | C20A—C21A | 1.3900 |
C7—C8 | 1.378 (3) | C20A—H20B | 0.9300 |
C7—H7 | 0.9300 | C21A—C22A | 1.3900 |
C8—C9 | 1.376 (4) | C21A—H21B | 0.9300 |
C8—H8 | 0.9300 | C22A—C23A | 1.3900 |
C9—C10 | 1.364 (4) | C22A—H22B | 0.9300 |
C10—C11 | 1.397 (3) | C23A—H23B | 0.9300 |
C10—H10 | 0.9300 | C25—H25A | 0.9600 |
C11—H11 | 0.9300 | C25—H25B | 0.9600 |
C12—H12D | 0.9600 | C25—H25C | 0.9600 |
C12—H12E | 0.9600 | ||
C1—Se1A—C18 | 101.2 (4) | C4—C13—H13 | 117.9 |
C18A—Se1B—C1 | 98.1 (5) | C13—C14—C15 | 122.1 (3) |
C9—O1—C12 | 117.8 (2) | C13—C14—H14 | 119.0 |
C24—N1—C25 | 119.50 (19) | C15—C14—H14 | 119.0 |
C24—N1—C2 | 120.49 (18) | O2B—C15—C16 | 127 (2) |
C25—N1—C2 | 118.50 (18) | O2A—C15—C16 | 118.7 (17) |
C5—C1—C2 | 113.3 (2) | O2B—C15—C14 | 116 (2) |
C5—C1—Se1A | 123.6 (2) | O2A—C15—C14 | 124.6 (17) |
C2—C1—Se1A | 123.1 (2) | C16—C15—C14 | 116.2 (2) |
C5—C1—Se1B | 123.5 (3) | C17—C16—C15 | 122.1 (3) |
C2—C1—Se1B | 122.7 (2) | C17—C16—H16 | 118.9 |
N1—C2—C1 | 111.31 (17) | C15—C16—H16 | 118.9 |
N1—C2—C3 | 114.34 (18) | C16—C17—C4 | 124.0 (2) |
C1—C2—C3 | 102.90 (17) | C16—C17—H17 | 118.0 |
N1—C2—H2 | 109.4 | C4—C17—H17 | 118.0 |
C1—C2—H2 | 109.4 | C19—C18—C23 | 120.0 |
C3—C2—H2 | 109.4 | C19—C18—Se1A | 108.8 (5) |
C2—C3—C4 | 106.98 (18) | C23—C18—Se1A | 131.2 (5) |
C2—C3—H3A | 110.3 | C20—C19—C18 | 120.0 |
C4—C3—H3A | 110.3 | C20—C19—H19A | 120.0 |
C2—C3—H3B | 110.3 | C18—C19—H19A | 120.0 |
C4—C3—H3B | 110.3 | C19—C20—C21 | 120.0 |
H3A—C3—H3B | 108.6 | C19—C20—H20A | 120.0 |
C13—C4—C17 | 111.3 (2) | C21—C20—H20A | 120.0 |
C13—C4—C5 | 113.1 (2) | C20—C21—C22 | 120.0 |
C17—C4—C5 | 107.56 (19) | C20—C21—H21A | 120.0 |
C13—C4—C3 | 110.4 (2) | C22—C21—H21A | 120.0 |
C17—C4—C3 | 112.87 (19) | C23—C22—C21 | 120.0 |
C5—C4—C3 | 101.28 (18) | C23—C22—H22A | 120.0 |
C1—C5—C6 | 126.2 (2) | C21—C22—H22A | 120.0 |
C1—C5—C4 | 111.1 (2) | C22—C23—C18 | 120.0 |
C6—C5—C4 | 122.2 (2) | C22—C23—H23A | 120.0 |
C11—C6—C7 | 117.8 (2) | C18—C23—H23A | 120.0 |
C11—C6—C5 | 122.4 (2) | C19A—C18A—C23A | 120.0 |
C7—C6—C5 | 119.7 (2) | C19A—C18A—Se1B | 134.5 (7) |
C8—C7—C6 | 121.3 (2) | C23A—C18A—Se1B | 105.5 (7) |
C8—C7—H7 | 119.3 | C20A—C19A—C18A | 120.0 |
C6—C7—H7 | 119.3 | C20A—C19A—H19B | 120.0 |
C9—C8—C7 | 119.6 (2) | C18A—C19A—H19B | 120.0 |
C9—C8—H8 | 120.2 | C21A—C20A—C19A | 120.0 |
C7—C8—H8 | 120.2 | C21A—C20A—H20B | 120.0 |
C10—C9—C8 | 120.8 (2) | C19A—C20A—H20B | 120.0 |
C10—C9—O1 | 124.5 (2) | C20A—C21A—C22A | 120.0 |
C8—C9—O1 | 114.7 (2) | C20A—C21A—H21B | 120.0 |
C9—C10—C11 | 119.4 (2) | C22A—C21A—H21B | 120.0 |
C9—C10—H10 | 120.3 | C21A—C22A—C23A | 120.0 |
C11—C10—H10 | 120.3 | C21A—C22A—H22B | 120.0 |
C6—C11—C10 | 121.0 (2) | C23A—C22A—H22B | 120.0 |
C6—C11—H11 | 119.5 | C22A—C23A—C18A | 120.0 |
C10—C11—H11 | 119.5 | C22A—C23A—H23B | 120.0 |
O1—C12—H12D | 109.5 | C18A—C23A—H23B | 120.0 |
O1—C12—H12E | 109.5 | N2—C24—N1 | 179.7 (4) |
H12D—C12—H12E | 109.5 | N1—C25—H25A | 109.5 |
O1—C12—H12F | 109.5 | N1—C25—H25B | 109.5 |
H12D—C12—H12F | 109.5 | H25A—C25—H25B | 109.5 |
H12E—C12—H12F | 109.5 | N1—C25—H25C | 109.5 |
C14—C13—C4 | 124.2 (3) | H25A—C25—H25C | 109.5 |
C14—C13—H13 | 117.9 | H25B—C25—H25C | 109.5 |
C18—Se1A—C1—C5 | −176.5 (3) | C12—O1—C9—C10 | −1.8 (4) |
C18—Se1A—C1—C2 | 3.1 (5) | C12—O1—C9—C8 | 178.5 (3) |
C24—N1—C2—C1 | 30.3 (3) | C8—C9—C10—C11 | 1.6 (4) |
C25—N1—C2—C1 | −163.8 (2) | O1—C9—C10—C11 | −178.0 (2) |
C24—N1—C2—C3 | −85.8 (3) | C7—C6—C11—C10 | −1.7 (4) |
C25—N1—C2—C3 | 80.2 (3) | C5—C6—C11—C10 | 177.3 (2) |
C5—C1—C2—N1 | −109.0 (2) | C9—C10—C11—C6 | 0.3 (4) |
Se1A—C1—C2—N1 | 71.3 (3) | C17—C4—C13—C14 | 1.3 (4) |
Se1B—C1—C2—N1 | 63.7 (4) | C5—C4—C13—C14 | −119.9 (3) |
C5—C1—C2—C3 | 13.9 (2) | C3—C4—C13—C14 | 127.4 (3) |
Se1A—C1—C2—C3 | −165.8 (3) | C4—C13—C14—C15 | 1.8 (5) |
Se1B—C1—C2—C3 | −173.4 (3) | C13—C14—C15—O2B | −171.4 (16) |
N1—C2—C3—C4 | 100.3 (2) | C13—C14—C15—O2A | 168.6 (13) |
C1—C2—C3—C4 | −20.6 (2) | C13—C14—C15—C16 | −3.2 (4) |
C2—C3—C4—C13 | 139.8 (2) | O2B—C15—C16—C17 | 168.1 (17) |
C2—C3—C4—C17 | −95.0 (2) | O2A—C15—C16—C17 | −171.0 (13) |
C2—C3—C4—C5 | 19.7 (2) | C14—C15—C16—C17 | 1.3 (4) |
C2—C1—C5—C6 | 170.7 (2) | C15—C16—C17—C4 | 2.0 (4) |
Se1A—C1—C5—C6 | −9.6 (4) | C13—C4—C17—C16 | −3.2 (3) |
Se1B—C1—C5—C6 | −1.9 (4) | C5—C4—C17—C16 | 121.2 (3) |
C2—C1—C5—C4 | −1.2 (3) | C3—C4—C17—C16 | −128.0 (3) |
Se1A—C1—C5—C4 | 178.5 (3) | C23—C18—C19—C20 | 0.0 |
Se1B—C1—C5—C4 | −173.9 (3) | Se1A—C18—C19—C20 | 179.8 (7) |
C13—C4—C5—C1 | −129.8 (2) | C18—C19—C20—C21 | 0.0 |
C17—C4—C5—C1 | 106.9 (2) | C19—C20—C21—C22 | 0.0 |
C3—C4—C5—C1 | −11.7 (2) | C20—C21—C22—C23 | 0.0 |
C13—C4—C5—C6 | 57.9 (3) | C21—C22—C23—C18 | 0.0 |
C17—C4—C5—C6 | −65.4 (3) | C19—C18—C23—C22 | 0.0 |
C3—C4—C5—C6 | 175.99 (19) | Se1A—C18—C23—C22 | −179.8 (8) |
C1—C5—C6—C11 | 125.9 (3) | C23A—C18A—C19A—C20A | 0.0 |
C4—C5—C6—C11 | −63.1 (3) | Se1B—C18A—C19A—C20A | 176.7 (11) |
C1—C5—C6—C7 | −55.1 (3) | C18A—C19A—C20A—C21A | 0.0 |
C4—C5—C6—C7 | 115.9 (2) | C19A—C20A—C21A—C22A | 0.0 |
C11—C6—C7—C8 | 1.2 (4) | C20A—C21A—C22A—C23A | 0.0 |
C5—C6—C7—C8 | −177.8 (2) | C21A—C22A—C23A—C18A | 0.0 |
C6—C7—C8—C9 | 0.6 (4) | C19A—C18A—C23A—C22A | 0.0 |
C7—C8—C9—C10 | −2.1 (4) | Se1B—C18A—C23A—C22A | −177.6 (8) |
C7—C8—C9—O1 | 177.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···N2i | 0.98 | 2.67 | 3.411 (4) | 132 |
C3—H3A···O2Aii | 0.97 | 2.58 | 3.55 (3) | 176 |
C3—H3A···O2Bii | 0.97 | 2.44 | 3.40 (4) | 168 |
C12—H12E···O2Aiii | 0.96 | 2.61 | 3.36 (3) | 135 |
C19—H19A···Se1Aiv | 0.93 | 3.04 | 3.876 (8) | 151 |
Symmetry codes: (i) x, y−1, z; (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y+2, −z+1; (iv) −x+1, y−1/2, −z+1/2. |
Funding information
Funding for this research was provided by: Robert A. Welch Foundation (grant No. 4-1362).
References
Bruker (2016). APEX2, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Singh, R. P., Gout, D. & Lovely, C. J. (2019). Eur. J. Org. Chem. 2019, 1726–1740. CSD CrossRef CAS Google Scholar
Singh, R. P., Spears, J. A., Dalipe, A., Yousufuddin, M. & Lovely, C. J. (2016). Tetrahedron Lett. 57, 3096–3099. Web of Science CSD CrossRef CAS Google Scholar
Yousufuddin, M., Morales, R., Cassis, W., Brown, G. W., Singh, R. P. & Lovely, C. J. (2018). IUCrData, 3, x180389. Google Scholar
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