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Two novel hypervalent selenium(IV) compounds stabilized by intramolecular interactions, namely 6-phenyl-6,7-dihydro-5
H-2,3-dioxa-2aλ
4-selenacyclopenta[
hi]indene, C
14H
12O
2Se,
14, and 5-phenyl-5,6-dihydro-4
H-benzo[
c][1,2]oxaselenole-7-carbaldehyde, C
14H
12OSe
2,
15, have been synthesized by the reaction of 2-chloro-1-formyl-3-(hydroxymethylene)cyclohexene with
in-situ-generated disodium diselenide (Na
2Se
2). The title compounds were characterized by FT–IR spectroscopy, ESI–MS, and single-crystal X-ray diffraction studies. For
14, there is whole-molecule disorder, with occupancies of 0.605 (10) and 0.395 (10), a double bond between C and Se, and the five-membered selenopentalene rings are coplanar. The packing is stabilized by π–π stacking interactions involving one of the five-membered Se/C/C/C/O rings [centroid–centroid (
CgCg) distance = 3.6472 (18) Å and slippage = 1.361 Å], as well as C—H
π interactions involving a C—H group and the phenyl ring. In addition, there are bifurcated C—H
Se,O interactions which link the molecules into ribbons in the
c direction. For
15, the C—Se bond lengths are longer than those of
14. The two five-membered rings are coplanar. There are no π–π or C—H
π interactions; however, molecules are linked by C—H
O interactions into centrosymmetric dimers, with graph-set notation
R22(16).
Supporting information
CCDC references: 1874547; 1874546
For both structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015). Program(s) used to solve structure: SIR92 (Altomare et al., 1993) for (14); SHELXT (Sheldrick, 2015a) for (15). For both structures, program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
6-Phenyl-6,7-dihydro-5
H-2,3-dioxa-2a
λ4-selenacyclopenta[
hi]\
indene (14)
top
Crystal data top
C14H12O2Se | F(000) = 584 |
Mr = 291.20 | Dx = 1.657 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8185 (4) Å | Cell parameters from 4480 reflections |
b = 17.4773 (7) Å | θ = 2.7–41.1° |
c = 7.9793 (4) Å | µ = 3.20 mm−1 |
β = 108.328 (5)° | T = 120 K |
V = 1167.41 (10) Å3 | Prism, colorless |
Z = 4 | 0.40 × 0.22 × 0.11 mm |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an Atlas detector | 4733 reflections with I > 2σ(I) |
Detector resolution: 10.6501 pixels mm-1 | Rint = 0.048 |
ω scans | θmax = 41.2°, θmin = 2.7° |
Absorption correction: analytical (CrysAlis PRO; Rigaku OD, 2015) | h = −15→16 |
Tmin = 0.379, Tmax = 0.711 | k = −27→32 |
15957 measured reflections | l = −11→14 |
7556 independent reflections | |
Refinement top
Refinement on F2 | 356 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0364P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
7556 reflections | Δρmax = 1.53 e Å−3 |
254 parameters | Δρmin = −1.13 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
SeA | 0.1674 (4) | 0.63962 (12) | 0.6047 (4) | 0.0194 (3) | 0.605 (10) |
O1A | 0.1866 (5) | 0.7216 (2) | 0.4171 (5) | 0.0254 (7) | 0.605 (10) |
O2A | 0.1474 (9) | 0.5457 (3) | 0.7399 (6) | 0.0194 (7) | 0.605 (10) |
C1A | 0.231 (2) | 0.5697 (5) | 0.4687 (19) | 0.0184 (11) | 0.605 (10) |
C2A | 0.2593 (17) | 0.5959 (5) | 0.3153 (11) | 0.0197 (11) | 0.605 (10) |
C3A | 0.3114 (14) | 0.5384 (5) | 0.2057 (15) | 0.0226 (12) | 0.605 (10) |
H3AA | 0.428516 | 0.531093 | 0.252145 | 0.027* | 0.605 (10) |
H3AB | 0.283592 | 0.556406 | 0.082051 | 0.027* | 0.605 (10) |
C4A | 0.2249 (11) | 0.4623 (5) | 0.2137 (9) | 0.0166 (10) | 0.605 (10) |
H4AA | 0.107193 | 0.471700 | 0.166079 | 0.020* | 0.605 (10) |
C5A | 0.2632 (12) | 0.4324 (6) | 0.4038 (12) | 0.0189 (12) | 0.605 (10) |
H5AA | 0.194096 | 0.387909 | 0.405240 | 0.023* | 0.605 (10) |
H5AB | 0.375776 | 0.415115 | 0.447123 | 0.023* | 0.605 (10) |
C6A | 0.2367 (14) | 0.4942 (5) | 0.5247 (13) | 0.0165 (11) | 0.605 (10) |
C7A | 0.2447 (16) | 0.6743 (5) | 0.2962 (13) | 0.0235 (12) | 0.605 (10) |
H7AA | 0.272539 | 0.698389 | 0.203252 | 0.028* | 0.605 (10) |
C8A | 0.1922 (15) | 0.4881 (5) | 0.6754 (13) | 0.0238 (12) | 0.605 (10) |
H8AA | 0.195744 | 0.439693 | 0.730635 | 0.029* | 0.605 (10) |
SeB | 0.1648 (6) | 0.6373 (2) | 0.6109 (7) | 0.0291 (8) | 0.395 (10) |
O1B | 0.1576 (14) | 0.5444 (4) | 0.7774 (8) | 0.0209 (11) | 0.395 (10) |
O2B | 0.2146 (6) | 0.7099 (3) | 0.4394 (7) | 0.0122 (8) | 0.395 (10) |
C1B | 0.218 (3) | 0.5656 (7) | 0.471 (3) | 0.0180 (18) | 0.395 (10) |
C2B | 0.219 (2) | 0.4884 (7) | 0.519 (2) | 0.0183 (17) | 0.395 (10) |
C3B | 0.2855 (18) | 0.4321 (8) | 0.4196 (18) | 0.0172 (15) | 0.395 (10) |
H3BA | 0.242074 | 0.380420 | 0.427436 | 0.021* | 0.395 (10) |
H3BB | 0.403283 | 0.429884 | 0.470605 | 0.021* | 0.395 (10) |
C4B | 0.238 (2) | 0.4580 (7) | 0.2251 (15) | 0.0245 (19) | 0.395 (10) |
H4BA | 0.119010 | 0.463167 | 0.188225 | 0.029* | 0.395 (10) |
C5B | 0.298 (2) | 0.5386 (8) | 0.203 (2) | 0.0253 (18) | 0.395 (10) |
H5BA | 0.414017 | 0.536527 | 0.220476 | 0.030* | 0.395 (10) |
H5BB | 0.243551 | 0.556937 | 0.081964 | 0.030* | 0.395 (10) |
C6B | 0.267 (2) | 0.5945 (7) | 0.3344 (18) | 0.0207 (16) | 0.395 (10) |
C7B | 0.180 (2) | 0.4783 (6) | 0.6717 (19) | 0.0193 (16) | 0.395 (10) |
H7BA | 0.166482 | 0.427932 | 0.709645 | 0.023* | 0.395 (10) |
C8B | 0.253 (3) | 0.6734 (7) | 0.3248 (19) | 0.029 (2) | 0.395 (10) |
H8BA | 0.273204 | 0.699924 | 0.230042 | 0.035* | 0.395 (10) |
C9 | 0.2672 (2) | 0.40047 (10) | 0.1019 (2) | 0.0206 (3) | |
C10 | 0.1473 (3) | 0.35150 (11) | 0.0048 (3) | 0.0254 (4) | |
H10A | 0.042442 | 0.356826 | 0.012411 | 0.031* | |
C11 | 0.1773 (3) | 0.29523 (12) | −0.1026 (3) | 0.0299 (5) | |
H11A | 0.092972 | 0.263118 | −0.169325 | 0.036* | |
C12 | 0.3300 (3) | 0.28561 (12) | −0.1129 (3) | 0.0290 (4) | |
H12A | 0.350936 | 0.247111 | −0.186726 | 0.035* | |
C13 | 0.4520 (3) | 0.33279 (12) | −0.0143 (3) | 0.0287 (4) | |
H13A | 0.557425 | 0.326083 | −0.019069 | 0.034* | |
C14 | 0.4206 (2) | 0.38954 (12) | 0.0909 (3) | 0.0260 (4) | |
H14A | 0.505075 | 0.421743 | 0.156936 | 0.031* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
SeA | 0.0209 (6) | 0.0164 (5) | 0.0216 (5) | 0.0001 (4) | 0.0077 (4) | −0.0052 (4) |
O1A | 0.0262 (15) | 0.0263 (14) | 0.0167 (10) | −0.0080 (11) | −0.0033 (10) | 0.0130 (10) |
O2A | 0.0224 (14) | 0.0296 (11) | 0.0069 (15) | −0.0001 (9) | 0.0057 (15) | −0.0063 (10) |
C1A | 0.018 (3) | 0.0184 (18) | 0.0186 (19) | −0.0036 (15) | 0.0051 (16) | −0.0015 (16) |
C2A | 0.027 (2) | 0.0169 (16) | 0.0151 (16) | 0.0039 (16) | 0.0069 (17) | 0.0032 (12) |
C3A | 0.027 (2) | 0.0190 (19) | 0.025 (2) | −0.0014 (16) | 0.0122 (18) | −0.0036 (18) |
C4A | 0.0176 (18) | 0.0191 (18) | 0.0122 (14) | 0.0013 (14) | 0.0034 (13) | 0.0006 (14) |
C5A | 0.021 (3) | 0.0173 (16) | 0.0160 (19) | 0.0036 (15) | 0.0020 (17) | −0.0008 (13) |
C6A | 0.017 (2) | 0.0176 (17) | 0.0144 (15) | −0.0029 (15) | 0.0034 (15) | −0.0016 (13) |
C7A | 0.035 (3) | 0.0167 (17) | 0.023 (3) | 0.0059 (16) | 0.016 (2) | 0.0026 (14) |
C8A | 0.027 (3) | 0.025 (2) | 0.0188 (18) | −0.008 (2) | 0.0056 (17) | 0.0013 (17) |
SeB | 0.0258 (12) | 0.0325 (13) | 0.0266 (11) | 0.0027 (10) | 0.0049 (8) | −0.0123 (9) |
O1B | 0.0191 (17) | 0.0300 (16) | 0.012 (2) | 0.0008 (13) | 0.003 (2) | −0.0068 (16) |
O2B | 0.0124 (11) | 0.0100 (10) | 0.0132 (11) | 0.0048 (7) | 0.0029 (8) | 0.0017 (8) |
C1B | 0.019 (4) | 0.019 (3) | 0.016 (3) | 0.000 (3) | 0.006 (2) | −0.005 (2) |
C2B | 0.018 (3) | 0.017 (3) | 0.018 (2) | −0.004 (2) | 0.003 (2) | −0.001 (2) |
C3B | 0.017 (3) | 0.022 (2) | 0.012 (2) | 0.000 (2) | 0.004 (2) | 0.002 (2) |
C4B | 0.033 (4) | 0.019 (3) | 0.023 (3) | 0.004 (3) | 0.011 (3) | 0.003 (3) |
C5B | 0.034 (4) | 0.024 (3) | 0.023 (3) | 0.003 (3) | 0.015 (3) | 0.004 (3) |
C6B | 0.022 (3) | 0.020 (3) | 0.023 (3) | −0.001 (2) | 0.011 (3) | −0.005 (2) |
C7B | 0.020 (3) | 0.020 (2) | 0.017 (2) | −0.005 (2) | 0.0049 (18) | −0.0045 (18) |
C8B | 0.042 (4) | 0.023 (3) | 0.025 (4) | −0.006 (3) | 0.013 (4) | 0.004 (3) |
C9 | 0.0255 (9) | 0.0180 (8) | 0.0189 (7) | 0.0004 (6) | 0.0080 (7) | 0.0005 (6) |
C10 | 0.0259 (9) | 0.0232 (9) | 0.0295 (9) | −0.0035 (7) | 0.0119 (8) | −0.0035 (7) |
C11 | 0.0355 (11) | 0.0240 (9) | 0.0311 (10) | −0.0069 (8) | 0.0119 (9) | −0.0078 (8) |
C12 | 0.0401 (12) | 0.0203 (8) | 0.0311 (9) | −0.0017 (8) | 0.0179 (9) | −0.0060 (7) |
C13 | 0.0306 (10) | 0.0222 (9) | 0.0378 (11) | 0.0022 (8) | 0.0172 (9) | −0.0054 (8) |
C14 | 0.0244 (9) | 0.0246 (9) | 0.0286 (9) | −0.0020 (7) | 0.0079 (8) | −0.0063 (8) |
Geometric parameters (Å, º) top
SeA—C1A | 1.835 (3) | C1B—C2B | 1.402 (13) |
SeA—O2A | 2.002 (5) | C2B—C7B | 1.379 (11) |
SeA—O1A | 2.117 (4) | C2B—C3B | 1.495 (12) |
O1A—C7A | 1.479 (10) | C3B—C4B | 1.543 (11) |
O2A—C8A | 1.250 (10) | C3B—H3BA | 0.9900 |
C1A—C6A | 1.389 (12) | C3B—H3BB | 0.9900 |
C1A—C2A | 1.402 (12) | C4B—C9 | 1.485 (10) |
C2A—C7A | 1.379 (9) | C4B—C5B | 1.534 (12) |
C2A—C3A | 1.496 (11) | C4B—H4BA | 1.0000 |
C3A—C4A | 1.544 (10) | C5B—C6B | 1.515 (12) |
C3A—H3AA | 0.9900 | C5B—H5BA | 0.9900 |
C3A—H3AB | 0.9900 | C5B—H5BB | 0.9900 |
C4A—C9 | 1.521 (6) | C6B—C8B | 1.384 (11) |
C4A—C5A | 1.538 (10) | C7B—H7BA | 0.9500 |
C4A—H4AA | 1.0000 | C8B—H8BA | 0.9500 |
C5A—C6A | 1.515 (11) | C9—C10 | 1.392 (3) |
C5A—H5AA | 0.9900 | C9—C14 | 1.396 (3) |
C5A—H5AB | 0.9900 | C10—C11 | 1.383 (3) |
C6A—C8A | 1.381 (10) | C10—H10A | 0.9500 |
C7A—H7AA | 0.9500 | C11—C12 | 1.385 (3) |
C8A—H8AA | 0.9500 | C11—H11A | 0.9500 |
SeB—C1B | 1.835 (3) | C12—C13 | 1.387 (3) |
SeB—O2B | 2.014 (6) | C12—H12A | 0.9500 |
SeB—O1B | 2.111 (6) | C13—C14 | 1.382 (3) |
O1B—C7B | 1.478 (10) | C13—H13A | 0.9500 |
O2B—C8B | 1.248 (11) | C14—H14A | 0.9500 |
C1B—C6B | 1.388 (13) | | |
| | | |
C1A—SeA—O2A | 82.4 (4) | C1B—C2B—C3B | 117.2 (9) |
C1A—SeA—O1A | 85.7 (4) | C2B—C3B—C4B | 108.2 (9) |
O2A—SeA—O1A | 167.41 (16) | C2B—C3B—H3BA | 110.1 |
C7A—O1A—SeA | 101.8 (4) | C4B—C3B—H3BA | 110.1 |
C8A—O2A—SeA | 110.2 (5) | C2B—C3B—H3BB | 110.1 |
C6A—C1A—C2A | 126.4 (3) | C4B—C3B—H3BB | 110.1 |
C6A—C1A—SeA | 115.4 (7) | H3BA—C3B—H3BB | 108.4 |
C2A—C1A—SeA | 118.0 (7) | C9—C4B—C5B | 114.2 (11) |
C7A—C2A—C1A | 112.6 (7) | C9—C4B—C3B | 114.7 (10) |
C7A—C2A—C3A | 129.6 (8) | C5B—C4B—C3B | 112.9 (5) |
C1A—C2A—C3A | 117.6 (7) | C9—C4B—H4BA | 104.5 |
C2A—C3A—C4A | 107.9 (7) | C5B—C4B—H4BA | 104.5 |
C2A—C3A—H3AA | 110.1 | C3B—C4B—H4BA | 104.5 |
C4A—C3A—H3AA | 110.1 | C6B—C5B—C4B | 111.8 (9) |
C2A—C3A—H3AB | 110.1 | C6B—C5B—H5BA | 109.3 |
C4A—C3A—H3AB | 110.1 | C4B—C5B—H5BA | 109.3 |
H3AA—C3A—H3AB | 108.4 | C6B—C5B—H5BB | 109.3 |
C9—C4A—C5A | 108.5 (6) | C4B—C5B—H5BB | 109.3 |
C9—C4A—C3A | 111.9 (7) | H5BA—C5B—H5BB | 107.9 |
C5A—C4A—C3A | 112.1 (3) | C8B—C6B—C1B | 111.2 (9) |
C9—C4A—H4AA | 108.1 | C8B—C6B—C5B | 129.5 (10) |
C5A—C4A—H4AA | 108.1 | C1B—C6B—C5B | 118.3 (9) |
C3A—C4A—H4AA | 108.1 | C2B—C7B—O1B | 121.3 (8) |
C6A—C5A—C4A | 110.8 (6) | C2B—C7B—H7BA | 119.4 |
C6A—C5A—H5AA | 109.5 | O1B—C7B—H7BA | 119.4 |
C4A—C5A—H5AA | 109.5 | O2B—C8B—C6B | 120.7 (9) |
C6A—C5A—H5AB | 109.5 | O2B—C8B—H8BA | 119.7 |
C4A—C5A—H5AB | 109.5 | C6B—C8B—H8BA | 119.7 |
H5AA—C5A—H5AB | 108.1 | C10—C9—C14 | 117.55 (19) |
C8A—C6A—C1A | 111.2 (7) | C10—C9—C4B | 121.7 (7) |
C8A—C6A—C5A | 130.0 (8) | C14—C9—C4B | 120.6 (7) |
C1A—C6A—C5A | 118.0 (7) | C10—C9—C4A | 118.7 (4) |
C2A—C7A—O1A | 121.5 (7) | C14—C9—C4A | 123.8 (4) |
C2A—C7A—H7AA | 119.3 | C11—C10—C9 | 121.5 (2) |
O1A—C7A—H7AA | 119.3 | C11—C10—H10A | 119.3 |
O2A—C8A—C6A | 120.6 (7) | C9—C10—H10A | 119.3 |
O2A—C8A—H8AA | 119.7 | C10—C11—C12 | 120.14 (19) |
C6A—C8A—H8AA | 119.7 | C10—C11—H11A | 119.9 |
C1B—SeB—O2B | 82.2 (5) | C12—C11—H11A | 119.9 |
C1B—SeB—O1B | 85.5 (5) | C11—C12—C13 | 119.3 (2) |
O2B—SeB—O1B | 165.6 (3) | C11—C12—H12A | 120.4 |
C7B—O1B—SeB | 101.9 (5) | C13—C12—H12A | 120.4 |
C8B—O2B—SeB | 110.1 (6) | C14—C13—C12 | 120.2 (2) |
C6B—C1B—C2B | 126.1 (4) | C14—C13—H13A | 119.9 |
C6B—C1B—SeB | 115.6 (8) | C12—C13—H13A | 119.9 |
C2B—C1B—SeB | 118.1 (9) | C13—C14—C9 | 121.29 (18) |
C7B—C2B—C1B | 112.5 (9) | C13—C14—H14A | 119.4 |
C7B—C2B—C3B | 129.4 (10) | C9—C14—H14A | 119.4 |
| | | |
O2A—SeA—C1A—C6A | −1.4 (11) | C1B—C2B—C3B—C4B | −37 (2) |
O1A—SeA—C1A—C6A | −177.3 (12) | C2B—C3B—C4B—C9 | −168.6 (15) |
O2A—SeA—C1A—C2A | 174.8 (15) | C2B—C3B—C4B—C5B | 58.3 (13) |
O1A—SeA—C1A—C2A | −1.0 (13) | C9—C4B—C5B—C6B | −179.1 (15) |
C6A—C1A—C2A—C7A | −180.0 (14) | C3B—C4B—C5B—C6B | −45.7 (15) |
SeA—C1A—C2A—C7A | 4.3 (18) | C2B—C1B—C6B—C8B | −179 (2) |
C6A—C1A—C2A—C3A | −4 (2) | SeB—C1B—C6B—C8B | −5 (3) |
SeA—C1A—C2A—C3A | 179.9 (10) | C2B—C1B—C6B—C5B | 11 (4) |
C7A—C2A—C3A—C4A | −149.7 (12) | SeB—C1B—C6B—C5B | −174.2 (16) |
C1A—C2A—C3A—C4A | 35.5 (17) | C4B—C5B—C6B—C8B | −156.4 (19) |
C2A—C3A—C4A—C9 | 178.6 (8) | C4B—C5B—C6B—C1B | 11 (3) |
C2A—C3A—C4A—C5A | −59.3 (9) | C1B—C2B—C7B—O1B | −6 (2) |
C9—C4A—C5A—C6A | 175.1 (9) | C3B—C2B—C7B—O1B | 163.0 (18) |
C3A—C4A—C5A—C6A | 51.1 (8) | SeB—O1B—C7B—C2B | 8.7 (17) |
C2A—C1A—C6A—C8A | −176.0 (16) | SeB—O2B—C8B—C6B | −4 (2) |
SeA—C1A—C6A—C8A | −0.1 (15) | C1B—C6B—C8B—O2B | 6 (3) |
C2A—C1A—C6A—C5A | −5 (2) | C5B—C6B—C8B—O2B | 174 (2) |
SeA—C1A—C6A—C5A | 170.7 (11) | C5B—C4B—C9—C10 | −131.7 (10) |
C4A—C5A—C6A—C8A | 150.2 (11) | C3B—C4B—C9—C10 | 95.8 (10) |
C4A—C5A—C6A—C1A | −18.6 (14) | C5B—C4B—C9—C14 | 53.7 (12) |
C1A—C2A—C7A—O1A | −6.6 (17) | C3B—C4B—C9—C14 | −78.8 (12) |
C3A—C2A—C7A—O1A | 178.4 (12) | C5A—C4A—C9—C10 | 95.5 (5) |
SeA—O1A—C7A—C2A | 5.4 (12) | C3A—C4A—C9—C10 | −140.3 (6) |
SeA—O2A—C8A—C6A | −3.9 (13) | C5A—C4A—C9—C14 | −84.3 (7) |
C1A—C6A—C8A—O2A | 2.9 (15) | C3A—C4A—C9—C14 | 39.8 (8) |
C5A—C6A—C8A—O2A | −166.6 (13) | C14—C9—C10—C11 | −1.6 (3) |
O2B—SeB—C1B—C6B | 2 (2) | C4B—C9—C10—C11 | −176.5 (7) |
O1B—SeB—C1B—C6B | −170 (2) | C4A—C9—C10—C11 | 178.5 (5) |
O2B—SeB—C1B—C2B | 177.0 (19) | C9—C10—C11—C12 | 1.2 (3) |
O1B—SeB—C1B—C2B | 4.6 (18) | C10—C11—C12—C13 | 0.2 (3) |
C6B—C1B—C2B—C7B | 174 (3) | C11—C12—C13—C14 | −1.0 (3) |
SeB—C1B—C2B—C7B | −1 (2) | C12—C13—C14—C9 | 0.5 (3) |
C6B—C1B—C2B—C3B | 3 (3) | C10—C9—C14—C13 | 0.8 (3) |
SeB—C1B—C2B—C3B | −171.3 (17) | C4B—C9—C14—C13 | 175.6 (7) |
C7B—C2B—C3B—C4B | 154.6 (17) | C4A—C9—C14—C13 | −179.4 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7Aa—H7AAa···SeAai | 0.95 | 3.01 | 3.567 (8) | 119 |
C7Aa—H7AAa···O1Aai | 0.95 | 2.58 | 3.428 (9) | 149 |
Symmetry code: (i) x, −y+3/2, z−1/2. |
5-Phenyl-5,6-dihydro-4
H-benzo[
c][1,2]oxaselenole-7-carbaldehyde (15)
top
Crystal data top
C14H12OSe2 | F(000) = 688 |
Mr = 354.16 | Dx = 1.906 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.1083 (2) Å | Cell parameters from 9896 reflections |
b = 13.8408 (3) Å | θ = 5.8–29.1° |
c = 12.5601 (4) Å | µ = 5.97 mm−1 |
β = 92.663 (2)° | T = 100 K |
V = 1234.39 (6) Å3 | Prism, yellow |
Z = 4 | 0.26 × 0.16 × 0.06 mm |
Data collection top
Rigaku Saturn724 CCD diffractometer | 3210 reflections with I > 2σ(I) |
ω scans | Rint = 0.093 |
Absorption correction: numerical (NUMABS; Higashi, 1999) | θmax = 31.2°, θmin = 4.4° |
Tmin = 0.086, Tmax = 0.442 | h = −8→8 |
3592 measured reflections | k = −16→16 |
3592 independent reflections | l = −14→14 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.147 | w = 1/[σ2(Fo2) + (0.0613P)2 + 3.1028P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3592 reflections | Δρmax = 2.13 e Å−3 |
155 parameters | Δρmin = −1.09 e Å−3 |
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. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Se1 | 0.30058 (5) | 0.38460 (3) | 0.26380 (3) | 0.02087 (14) | |
Se2 | 0.22249 (5) | 0.46181 (3) | 0.09784 (4) | 0.02753 (15) | |
O1 | 0.4344 (4) | 0.3257 (2) | 0.4280 (2) | 0.0218 (5) | |
C1 | 0.5087 (5) | 0.4669 (3) | 0.2863 (3) | 0.0191 (7) | |
C2 | 0.5442 (5) | 0.5374 (3) | 0.2044 (4) | 0.0247 (8) | |
C3 | 0.7230 (6) | 0.5973 (4) | 0.2160 (4) | 0.0323 (9) | |
H3A | 0.827376 | 0.562325 | 0.183411 | 0.039* | |
H3B | 0.704192 | 0.659307 | 0.177669 | 0.039* | |
C4 | 0.7745 (6) | 0.6170 (3) | 0.3320 (4) | 0.0280 (9) | |
H4 | 0.668097 | 0.654061 | 0.361539 | 0.034* | |
C5 | 0.7934 (5) | 0.5208 (3) | 0.3957 (4) | 0.0238 (8) | |
H5A | 0.907564 | 0.486138 | 0.374598 | 0.029* | |
H5B | 0.808833 | 0.535651 | 0.472762 | 0.029* | |
C6 | 0.6235 (5) | 0.4562 (3) | 0.3766 (3) | 0.0205 (7) | |
C7 | 0.4253 (6) | 0.5453 (3) | 0.1185 (4) | 0.0264 (8) | |
H7 | 0.445301 | 0.594426 | 0.067442 | 0.032* | |
C8 | 0.5745 (6) | 0.3832 (3) | 0.4485 (4) | 0.0255 (8) | |
H8 | 0.646413 | 0.376173 | 0.513696 | 0.031* | |
C9 | 0.9499 (6) | 0.6780 (3) | 0.3481 (3) | 0.0289 (9) | |
C10 | 1.0923 (7) | 0.6835 (4) | 0.2759 (4) | 0.0347 (10) | |
H10 | 1.086007 | 0.643539 | 0.214314 | 0.042* | |
C11 | 1.2429 (6) | 0.7460 (3) | 0.2922 (4) | 0.0290 (9) | |
H11 | 1.337292 | 0.750165 | 0.241227 | 0.035* | |
C12 | 1.2548 (6) | 0.8022 (3) | 0.3829 (4) | 0.0269 (8) | |
H12 | 1.356155 | 0.846331 | 0.394309 | 0.032* | |
C13 | 1.1176 (6) | 0.7939 (3) | 0.4576 (4) | 0.0291 (9) | |
H13 | 1.126722 | 0.831209 | 0.521062 | 0.035* | |
C14 | 0.9679 (6) | 0.7315 (3) | 0.4397 (4) | 0.0284 (8) | |
H14 | 0.875966 | 0.725566 | 0.491874 | 0.034* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Se1 | 0.01223 (18) | 0.0206 (2) | 0.0299 (3) | −0.00103 (11) | 0.00277 (14) | −0.00151 (14) |
Se2 | 0.0183 (2) | 0.0294 (2) | 0.0341 (3) | −0.00239 (13) | −0.00616 (16) | 0.00050 (16) |
O1 | 0.0165 (11) | 0.0265 (13) | 0.0231 (14) | −0.0034 (10) | 0.0078 (9) | 0.0040 (11) |
C1 | 0.0153 (15) | 0.0172 (15) | 0.0248 (19) | 0.0004 (11) | 0.0011 (13) | −0.0011 (13) |
C2 | 0.0195 (16) | 0.0190 (17) | 0.035 (2) | −0.0032 (12) | −0.0042 (15) | 0.0061 (15) |
C3 | 0.0239 (19) | 0.031 (2) | 0.041 (3) | −0.0058 (16) | −0.0055 (17) | 0.0096 (19) |
C4 | 0.0230 (18) | 0.033 (2) | 0.028 (2) | −0.0039 (14) | 0.0005 (15) | 0.0012 (16) |
C5 | 0.0157 (16) | 0.0234 (17) | 0.032 (2) | 0.0017 (12) | −0.0050 (14) | −0.0019 (15) |
C6 | 0.0153 (15) | 0.0179 (16) | 0.028 (2) | 0.0025 (11) | −0.0008 (13) | −0.0033 (14) |
C7 | 0.0216 (17) | 0.0235 (18) | 0.033 (2) | −0.0031 (13) | −0.0068 (15) | 0.0059 (16) |
C8 | 0.0215 (17) | 0.028 (2) | 0.027 (2) | 0.0035 (14) | 0.0032 (14) | 0.0005 (15) |
C9 | 0.0229 (18) | 0.039 (2) | 0.024 (2) | −0.0130 (16) | −0.0013 (14) | 0.0034 (17) |
C10 | 0.038 (2) | 0.040 (2) | 0.027 (2) | −0.0219 (19) | 0.0059 (17) | −0.0082 (19) |
C11 | 0.0250 (19) | 0.033 (2) | 0.030 (2) | −0.0155 (16) | 0.0079 (15) | −0.0006 (17) |
C12 | 0.0294 (19) | 0.0225 (17) | 0.029 (2) | −0.0110 (15) | 0.0028 (15) | −0.0013 (16) |
C13 | 0.0283 (19) | 0.0270 (19) | 0.032 (2) | −0.0023 (15) | 0.0048 (16) | −0.0062 (17) |
C14 | 0.0193 (17) | 0.039 (2) | 0.027 (2) | −0.0034 (15) | 0.0051 (14) | 0.0034 (17) |
Geometric parameters (Å, º) top
Se1—C1 | 1.878 (4) | C5—H5A | 0.9900 |
Se1—O1 | 2.375 (3) | C5—H5B | 0.9900 |
Se1—Se2 | 2.3849 (6) | C6—C8 | 1.409 (6) |
Se2—C7 | 1.856 (4) | C7—H7 | 0.9500 |
O1—C8 | 1.292 (5) | C8—H8 | 0.9500 |
C1—C6 | 1.375 (5) | C9—C14 | 1.370 (7) |
C1—C2 | 1.449 (6) | C9—C10 | 1.392 (6) |
C2—C7 | 1.344 (6) | C10—C11 | 1.384 (5) |
C2—C3 | 1.518 (6) | C10—H10 | 0.9500 |
C3—C4 | 1.511 (7) | C11—C12 | 1.380 (6) |
C3—H3A | 0.9900 | C11—H11 | 0.9500 |
C3—H3B | 0.9900 | C12—C13 | 1.389 (6) |
C4—C9 | 1.511 (6) | C12—H12 | 0.9500 |
C4—C5 | 1.555 (6) | C13—C14 | 1.380 (6) |
C4—H4 | 1.0000 | C13—H13 | 0.9500 |
C5—C6 | 1.512 (5) | C14—H14 | 0.9500 |
| | | |
C1—Se1—O1 | 78.26 (14) | H5A—C5—H5B | 107.9 |
C1—Se1—Se2 | 90.54 (12) | C1—C6—C8 | 116.8 (4) |
O1—Se1—Se2 | 168.62 (7) | C1—C6—C5 | 120.4 (4) |
C7—Se2—Se1 | 90.52 (14) | C8—C6—C5 | 122.8 (4) |
C8—O1—Se1 | 103.6 (2) | C2—C7—Se2 | 121.2 (3) |
C6—C1—C2 | 122.8 (3) | C2—C7—H7 | 119.4 |
C6—C1—Se1 | 119.5 (3) | Se2—C7—H7 | 119.4 |
C2—C1—Se1 | 117.6 (3) | O1—C8—C6 | 121.7 (4) |
C7—C2—C1 | 120.0 (4) | O1—C8—H8 | 119.1 |
C7—C2—C3 | 121.7 (4) | C6—C8—H8 | 119.1 |
C1—C2—C3 | 118.2 (4) | C14—C9—C10 | 118.4 (4) |
C4—C3—C2 | 110.8 (4) | C14—C9—C4 | 117.3 (4) |
C4—C3—H3A | 109.5 | C10—C9—C4 | 124.3 (4) |
C2—C3—H3A | 109.5 | C11—C10—C9 | 121.2 (4) |
C4—C3—H3B | 109.5 | C11—C10—H10 | 119.4 |
C2—C3—H3B | 109.5 | C9—C10—H10 | 119.4 |
H3A—C3—H3B | 108.1 | C12—C11—C10 | 119.5 (4) |
C3—C4—C9 | 113.0 (4) | C12—C11—H11 | 120.3 |
C3—C4—C5 | 110.7 (4) | C10—C11—H11 | 120.3 |
C9—C4—C5 | 111.0 (3) | C11—C12—C13 | 119.5 (4) |
C3—C4—H4 | 107.3 | C11—C12—H12 | 120.2 |
C9—C4—H4 | 107.3 | C13—C12—H12 | 120.2 |
C5—C4—H4 | 107.3 | C14—C13—C12 | 120.2 (4) |
C6—C5—C4 | 112.0 (3) | C14—C13—H13 | 119.9 |
C6—C5—H5A | 109.2 | C12—C13—H13 | 119.9 |
C4—C5—H5A | 109.2 | C9—C14—C13 | 121.1 (4) |
C6—C5—H5B | 109.2 | C9—C14—H14 | 119.5 |
C4—C5—H5B | 109.2 | C13—C14—H14 | 119.5 |
| | | |
O1—Se1—C1—C6 | −0.9 (3) | C4—C5—C6—C8 | −157.9 (4) |
Se2—Se1—C1—C6 | −178.9 (3) | C1—C2—C7—Se2 | −4.0 (6) |
O1—Se1—C1—C2 | 177.0 (3) | C3—C2—C7—Se2 | 172.8 (3) |
Se2—Se1—C1—C2 | −0.9 (3) | Se1—Se2—C7—C2 | 2.6 (4) |
C6—C1—C2—C7 | −179.0 (4) | Se1—O1—C8—C6 | −3.8 (4) |
Se1—C1—C2—C7 | 3.1 (6) | C1—C6—C8—O1 | 3.5 (6) |
C6—C1—C2—C3 | 4.1 (6) | C5—C6—C8—O1 | −176.4 (4) |
Se1—C1—C2—C3 | −173.8 (3) | C3—C4—C9—C14 | 154.4 (4) |
C7—C2—C3—C4 | 149.9 (4) | C5—C4—C9—C14 | −80.5 (5) |
C1—C2—C3—C4 | −33.3 (6) | C3—C4—C9—C10 | −25.2 (7) |
C2—C3—C4—C9 | −179.0 (4) | C5—C4—C9—C10 | 99.9 (5) |
C2—C3—C4—C5 | 55.8 (5) | C14—C9—C10—C11 | −4.2 (8) |
C3—C4—C5—C6 | −50.8 (5) | C4—C9—C10—C11 | 175.4 (5) |
C9—C4—C5—C6 | −177.2 (4) | C9—C10—C11—C12 | 1.7 (8) |
C2—C1—C6—C8 | −178.6 (3) | C10—C11—C12—C13 | 1.2 (7) |
Se1—C1—C6—C8 | −0.7 (5) | C11—C12—C13—C14 | −1.6 (7) |
C2—C1—C6—C5 | 1.4 (6) | C10—C9—C14—C13 | 3.9 (7) |
Se1—C1—C6—C5 | 179.2 (3) | C4—C9—C14—C13 | −175.8 (4) |
C4—C5—C6—C1 | 22.2 (5) | C12—C13—C14—C9 | −1.0 (7) |
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