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Two novel hypervalent selenium(IV) compounds stabilized by intra­molecular inter­actions, namely 6-phenyl-6,7-di­hydro-5H-2,3-dioxa-2aλ4-selena­cyclo­penta­[hi]indene, C14H12O2Se, 14, and 5-phenyl-5,6-di­hydro-4H-benzo[c][1,2]oxa­selenole-7-carbaldehyde, C14H12OSe2, 15, have been synthesized by the reaction of 2-chloro-1-formyl-3-(hy­droxy­methyl­ene)­cyclo­hexene with in-situ-generated disodium diselenide (Na2Se2). 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 (Cg...Cg) 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618014833/cu3133sup1.cif
Contains datablocks 14, 15, shelx

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014833/cu313314sup2.hkl
Contains datablock 14

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014833/cu313315sup3.hkl
Contains datablock 15

CCDC references: 1874547; 1874546

Computing details top

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-5H-2,3-dioxa-2aλ4-selenacyclopenta[hi]\ indene (14) top
Crystal data top
C14H12O2SeF(000) = 584
Mr = 291.20Dx = 1.657 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.8185 (4) ÅCell parameters from 4480 reflections
b = 17.4773 (7) Åθ = 2.7–41.1°
c = 7.9793 (4) ŵ = 3.20 mm1
β = 108.328 (5)°T = 120 K
V = 1167.41 (10) Å3Prism, colorless
Z = 40.40 × 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-1Rint = 0.048
ω scansθmax = 41.2°, θmin = 2.7°
Absorption correction: analytical
(CrysAlis PRO; Rigaku OD, 2015)
h = 1516
Tmin = 0.379, Tmax = 0.711k = 2732
15957 measured reflectionsl = 1114
7556 independent reflections
Refinement top
Refinement on F2356 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-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 reflectionsΔρmax = 1.53 e Å3
254 parametersΔρmin = 1.13 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
SeA0.1674 (4)0.63962 (12)0.6047 (4)0.0194 (3)0.605 (10)
O1A0.1866 (5)0.7216 (2)0.4171 (5)0.0254 (7)0.605 (10)
O2A0.1474 (9)0.5457 (3)0.7399 (6)0.0194 (7)0.605 (10)
C1A0.231 (2)0.5697 (5)0.4687 (19)0.0184 (11)0.605 (10)
C2A0.2593 (17)0.5959 (5)0.3153 (11)0.0197 (11)0.605 (10)
C3A0.3114 (14)0.5384 (5)0.2057 (15)0.0226 (12)0.605 (10)
H3AA0.4285160.5310930.2521450.027*0.605 (10)
H3AB0.2835920.5564060.0820510.027*0.605 (10)
C4A0.2249 (11)0.4623 (5)0.2137 (9)0.0166 (10)0.605 (10)
H4AA0.1071930.4717000.1660790.020*0.605 (10)
C5A0.2632 (12)0.4324 (6)0.4038 (12)0.0189 (12)0.605 (10)
H5AA0.1940960.3879090.4052400.023*0.605 (10)
H5AB0.3757760.4151150.4471230.023*0.605 (10)
C6A0.2367 (14)0.4942 (5)0.5247 (13)0.0165 (11)0.605 (10)
C7A0.2447 (16)0.6743 (5)0.2962 (13)0.0235 (12)0.605 (10)
H7AA0.2725390.6983890.2032520.028*0.605 (10)
C8A0.1922 (15)0.4881 (5)0.6754 (13)0.0238 (12)0.605 (10)
H8AA0.1957440.4396930.7306350.029*0.605 (10)
SeB0.1648 (6)0.6373 (2)0.6109 (7)0.0291 (8)0.395 (10)
O1B0.1576 (14)0.5444 (4)0.7774 (8)0.0209 (11)0.395 (10)
O2B0.2146 (6)0.7099 (3)0.4394 (7)0.0122 (8)0.395 (10)
C1B0.218 (3)0.5656 (7)0.471 (3)0.0180 (18)0.395 (10)
C2B0.219 (2)0.4884 (7)0.519 (2)0.0183 (17)0.395 (10)
C3B0.2855 (18)0.4321 (8)0.4196 (18)0.0172 (15)0.395 (10)
H3BA0.2420740.3804200.4274360.021*0.395 (10)
H3BB0.4032830.4298840.4706050.021*0.395 (10)
C4B0.238 (2)0.4580 (7)0.2251 (15)0.0245 (19)0.395 (10)
H4BA0.1190100.4631670.1882250.029*0.395 (10)
C5B0.298 (2)0.5386 (8)0.203 (2)0.0253 (18)0.395 (10)
H5BA0.4140170.5365270.2204760.030*0.395 (10)
H5BB0.2435510.5569370.0819640.030*0.395 (10)
C6B0.267 (2)0.5945 (7)0.3344 (18)0.0207 (16)0.395 (10)
C7B0.180 (2)0.4783 (6)0.6717 (19)0.0193 (16)0.395 (10)
H7BA0.1664820.4279320.7096450.023*0.395 (10)
C8B0.253 (3)0.6734 (7)0.3248 (19)0.029 (2)0.395 (10)
H8BA0.2732040.6999240.2300420.035*0.395 (10)
C90.2672 (2)0.40047 (10)0.1019 (2)0.0206 (3)
C100.1473 (3)0.35150 (11)0.0048 (3)0.0254 (4)
H10A0.0424420.3568260.0124110.031*
C110.1773 (3)0.29523 (12)0.1026 (3)0.0299 (5)
H11A0.0929720.2631180.1693250.036*
C120.3300 (3)0.28561 (12)0.1129 (3)0.0290 (4)
H12A0.3509360.2471110.1867260.035*
C130.4520 (3)0.33279 (12)0.0143 (3)0.0287 (4)
H13A0.5574250.3260830.0190690.034*
C140.4206 (2)0.38954 (12)0.0909 (3)0.0260 (4)
H14A0.5050750.4217430.1569360.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
SeA0.0209 (6)0.0164 (5)0.0216 (5)0.0001 (4)0.0077 (4)0.0052 (4)
O1A0.0262 (15)0.0263 (14)0.0167 (10)0.0080 (11)0.0033 (10)0.0130 (10)
O2A0.0224 (14)0.0296 (11)0.0069 (15)0.0001 (9)0.0057 (15)0.0063 (10)
C1A0.018 (3)0.0184 (18)0.0186 (19)0.0036 (15)0.0051 (16)0.0015 (16)
C2A0.027 (2)0.0169 (16)0.0151 (16)0.0039 (16)0.0069 (17)0.0032 (12)
C3A0.027 (2)0.0190 (19)0.025 (2)0.0014 (16)0.0122 (18)0.0036 (18)
C4A0.0176 (18)0.0191 (18)0.0122 (14)0.0013 (14)0.0034 (13)0.0006 (14)
C5A0.021 (3)0.0173 (16)0.0160 (19)0.0036 (15)0.0020 (17)0.0008 (13)
C6A0.017 (2)0.0176 (17)0.0144 (15)0.0029 (15)0.0034 (15)0.0016 (13)
C7A0.035 (3)0.0167 (17)0.023 (3)0.0059 (16)0.016 (2)0.0026 (14)
C8A0.027 (3)0.025 (2)0.0188 (18)0.008 (2)0.0056 (17)0.0013 (17)
SeB0.0258 (12)0.0325 (13)0.0266 (11)0.0027 (10)0.0049 (8)0.0123 (9)
O1B0.0191 (17)0.0300 (16)0.012 (2)0.0008 (13)0.003 (2)0.0068 (16)
O2B0.0124 (11)0.0100 (10)0.0132 (11)0.0048 (7)0.0029 (8)0.0017 (8)
C1B0.019 (4)0.019 (3)0.016 (3)0.000 (3)0.006 (2)0.005 (2)
C2B0.018 (3)0.017 (3)0.018 (2)0.004 (2)0.003 (2)0.001 (2)
C3B0.017 (3)0.022 (2)0.012 (2)0.000 (2)0.004 (2)0.002 (2)
C4B0.033 (4)0.019 (3)0.023 (3)0.004 (3)0.011 (3)0.003 (3)
C5B0.034 (4)0.024 (3)0.023 (3)0.003 (3)0.015 (3)0.004 (3)
C6B0.022 (3)0.020 (3)0.023 (3)0.001 (2)0.011 (3)0.005 (2)
C7B0.020 (3)0.020 (2)0.017 (2)0.005 (2)0.0049 (18)0.0045 (18)
C8B0.042 (4)0.023 (3)0.025 (4)0.006 (3)0.013 (4)0.004 (3)
C90.0255 (9)0.0180 (8)0.0189 (7)0.0004 (6)0.0080 (7)0.0005 (6)
C100.0259 (9)0.0232 (9)0.0295 (9)0.0035 (7)0.0119 (8)0.0035 (7)
C110.0355 (11)0.0240 (9)0.0311 (10)0.0069 (8)0.0119 (9)0.0078 (8)
C120.0401 (12)0.0203 (8)0.0311 (9)0.0017 (8)0.0179 (9)0.0060 (7)
C130.0306 (10)0.0222 (9)0.0378 (11)0.0022 (8)0.0172 (9)0.0054 (8)
C140.0244 (9)0.0246 (9)0.0286 (9)0.0020 (7)0.0079 (8)0.0063 (8)
Geometric parameters (Å, º) top
SeA—C1A1.835 (3)C1B—C2B1.402 (13)
SeA—O2A2.002 (5)C2B—C7B1.379 (11)
SeA—O1A2.117 (4)C2B—C3B1.495 (12)
O1A—C7A1.479 (10)C3B—C4B1.543 (11)
O2A—C8A1.250 (10)C3B—H3BA0.9900
C1A—C6A1.389 (12)C3B—H3BB0.9900
C1A—C2A1.402 (12)C4B—C91.485 (10)
C2A—C7A1.379 (9)C4B—C5B1.534 (12)
C2A—C3A1.496 (11)C4B—H4BA1.0000
C3A—C4A1.544 (10)C5B—C6B1.515 (12)
C3A—H3AA0.9900C5B—H5BA0.9900
C3A—H3AB0.9900C5B—H5BB0.9900
C4A—C91.521 (6)C6B—C8B1.384 (11)
C4A—C5A1.538 (10)C7B—H7BA0.9500
C4A—H4AA1.0000C8B—H8BA0.9500
C5A—C6A1.515 (11)C9—C101.392 (3)
C5A—H5AA0.9900C9—C141.396 (3)
C5A—H5AB0.9900C10—C111.383 (3)
C6A—C8A1.381 (10)C10—H10A0.9500
C7A—H7AA0.9500C11—C121.385 (3)
C8A—H8AA0.9500C11—H11A0.9500
SeB—C1B1.835 (3)C12—C131.387 (3)
SeB—O2B2.014 (6)C12—H12A0.9500
SeB—O1B2.111 (6)C13—C141.382 (3)
O1B—C7B1.478 (10)C13—H13A0.9500
O2B—C8B1.248 (11)C14—H14A0.9500
C1B—C6B1.388 (13)
C1A—SeA—O2A82.4 (4)C1B—C2B—C3B117.2 (9)
C1A—SeA—O1A85.7 (4)C2B—C3B—C4B108.2 (9)
O2A—SeA—O1A167.41 (16)C2B—C3B—H3BA110.1
C7A—O1A—SeA101.8 (4)C4B—C3B—H3BA110.1
C8A—O2A—SeA110.2 (5)C2B—C3B—H3BB110.1
C6A—C1A—C2A126.4 (3)C4B—C3B—H3BB110.1
C6A—C1A—SeA115.4 (7)H3BA—C3B—H3BB108.4
C2A—C1A—SeA118.0 (7)C9—C4B—C5B114.2 (11)
C7A—C2A—C1A112.6 (7)C9—C4B—C3B114.7 (10)
C7A—C2A—C3A129.6 (8)C5B—C4B—C3B112.9 (5)
C1A—C2A—C3A117.6 (7)C9—C4B—H4BA104.5
C2A—C3A—C4A107.9 (7)C5B—C4B—H4BA104.5
C2A—C3A—H3AA110.1C3B—C4B—H4BA104.5
C4A—C3A—H3AA110.1C6B—C5B—C4B111.8 (9)
C2A—C3A—H3AB110.1C6B—C5B—H5BA109.3
C4A—C3A—H3AB110.1C4B—C5B—H5BA109.3
H3AA—C3A—H3AB108.4C6B—C5B—H5BB109.3
C9—C4A—C5A108.5 (6)C4B—C5B—H5BB109.3
C9—C4A—C3A111.9 (7)H5BA—C5B—H5BB107.9
C5A—C4A—C3A112.1 (3)C8B—C6B—C1B111.2 (9)
C9—C4A—H4AA108.1C8B—C6B—C5B129.5 (10)
C5A—C4A—H4AA108.1C1B—C6B—C5B118.3 (9)
C3A—C4A—H4AA108.1C2B—C7B—O1B121.3 (8)
C6A—C5A—C4A110.8 (6)C2B—C7B—H7BA119.4
C6A—C5A—H5AA109.5O1B—C7B—H7BA119.4
C4A—C5A—H5AA109.5O2B—C8B—C6B120.7 (9)
C6A—C5A—H5AB109.5O2B—C8B—H8BA119.7
C4A—C5A—H5AB109.5C6B—C8B—H8BA119.7
H5AA—C5A—H5AB108.1C10—C9—C14117.55 (19)
C8A—C6A—C1A111.2 (7)C10—C9—C4B121.7 (7)
C8A—C6A—C5A130.0 (8)C14—C9—C4B120.6 (7)
C1A—C6A—C5A118.0 (7)C10—C9—C4A118.7 (4)
C2A—C7A—O1A121.5 (7)C14—C9—C4A123.8 (4)
C2A—C7A—H7AA119.3C11—C10—C9121.5 (2)
O1A—C7A—H7AA119.3C11—C10—H10A119.3
O2A—C8A—C6A120.6 (7)C9—C10—H10A119.3
O2A—C8A—H8AA119.7C10—C11—C12120.14 (19)
C6A—C8A—H8AA119.7C10—C11—H11A119.9
C1B—SeB—O2B82.2 (5)C12—C11—H11A119.9
C1B—SeB—O1B85.5 (5)C11—C12—C13119.3 (2)
O2B—SeB—O1B165.6 (3)C11—C12—H12A120.4
C7B—O1B—SeB101.9 (5)C13—C12—H12A120.4
C8B—O2B—SeB110.1 (6)C14—C13—C12120.2 (2)
C6B—C1B—C2B126.1 (4)C14—C13—H13A119.9
C6B—C1B—SeB115.6 (8)C12—C13—H13A119.9
C2B—C1B—SeB118.1 (9)C13—C14—C9121.29 (18)
C7B—C2B—C1B112.5 (9)C13—C14—H14A119.4
C7B—C2B—C3B129.4 (10)C9—C14—H14A119.4
O2A—SeA—C1A—C6A1.4 (11)C1B—C2B—C3B—C4B37 (2)
O1A—SeA—C1A—C6A177.3 (12)C2B—C3B—C4B—C9168.6 (15)
O2A—SeA—C1A—C2A174.8 (15)C2B—C3B—C4B—C5B58.3 (13)
O1A—SeA—C1A—C2A1.0 (13)C9—C4B—C5B—C6B179.1 (15)
C6A—C1A—C2A—C7A180.0 (14)C3B—C4B—C5B—C6B45.7 (15)
SeA—C1A—C2A—C7A4.3 (18)C2B—C1B—C6B—C8B179 (2)
C6A—C1A—C2A—C3A4 (2)SeB—C1B—C6B—C8B5 (3)
SeA—C1A—C2A—C3A179.9 (10)C2B—C1B—C6B—C5B11 (4)
C7A—C2A—C3A—C4A149.7 (12)SeB—C1B—C6B—C5B174.2 (16)
C1A—C2A—C3A—C4A35.5 (17)C4B—C5B—C6B—C8B156.4 (19)
C2A—C3A—C4A—C9178.6 (8)C4B—C5B—C6B—C1B11 (3)
C2A—C3A—C4A—C5A59.3 (9)C1B—C2B—C7B—O1B6 (2)
C9—C4A—C5A—C6A175.1 (9)C3B—C2B—C7B—O1B163.0 (18)
C3A—C4A—C5A—C6A51.1 (8)SeB—O1B—C7B—C2B8.7 (17)
C2A—C1A—C6A—C8A176.0 (16)SeB—O2B—C8B—C6B4 (2)
SeA—C1A—C6A—C8A0.1 (15)C1B—C6B—C8B—O2B6 (3)
C2A—C1A—C6A—C5A5 (2)C5B—C6B—C8B—O2B174 (2)
SeA—C1A—C6A—C5A170.7 (11)C5B—C4B—C9—C10131.7 (10)
C4A—C5A—C6A—C8A150.2 (11)C3B—C4B—C9—C1095.8 (10)
C4A—C5A—C6A—C1A18.6 (14)C5B—C4B—C9—C1453.7 (12)
C1A—C2A—C7A—O1A6.6 (17)C3B—C4B—C9—C1478.8 (12)
C3A—C2A—C7A—O1A178.4 (12)C5A—C4A—C9—C1095.5 (5)
SeA—O1A—C7A—C2A5.4 (12)C3A—C4A—C9—C10140.3 (6)
SeA—O2A—C8A—C6A3.9 (13)C5A—C4A—C9—C1484.3 (7)
C1A—C6A—C8A—O2A2.9 (15)C3A—C4A—C9—C1439.8 (8)
C5A—C6A—C8A—O2A166.6 (13)C14—C9—C10—C111.6 (3)
O2B—SeB—C1B—C6B2 (2)C4B—C9—C10—C11176.5 (7)
O1B—SeB—C1B—C6B170 (2)C4A—C9—C10—C11178.5 (5)
O2B—SeB—C1B—C2B177.0 (19)C9—C10—C11—C121.2 (3)
O1B—SeB—C1B—C2B4.6 (18)C10—C11—C12—C130.2 (3)
C6B—C1B—C2B—C7B174 (3)C11—C12—C13—C141.0 (3)
SeB—C1B—C2B—C7B1 (2)C12—C13—C14—C90.5 (3)
C6B—C1B—C2B—C3B3 (3)C10—C9—C14—C130.8 (3)
SeB—C1B—C2B—C3B171.3 (17)C4B—C9—C14—C13175.6 (7)
C7B—C2B—C3B—C4B154.6 (17)C4A—C9—C14—C13179.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7Aa—H7AAa···SeAai0.953.013.567 (8)119
C7Aa—H7AAa···O1Aai0.952.583.428 (9)149
Symmetry code: (i) x, y+3/2, z1/2.
5-Phenyl-5,6-dihydro-4H-benzo[c][1,2]oxaselenole-7-carbaldehyde (15) top
Crystal data top
C14H12OSe2F(000) = 688
Mr = 354.16Dx = 1.906 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.1083 (2) ÅCell parameters from 9896 reflections
b = 13.8408 (3) Åθ = 5.8–29.1°
c = 12.5601 (4) ŵ = 5.97 mm1
β = 92.663 (2)°T = 100 K
V = 1234.39 (6) Å3Prism, yellow
Z = 40.26 × 0.16 × 0.06 mm
Data collection top
Rigaku Saturn724 CCD
diffractometer
3210 reflections with I > 2σ(I)
ω scansRint = 0.093
Absorption correction: numerical
(NUMABS; Higashi, 1999)
θmax = 31.2°, θmin = 4.4°
Tmin = 0.086, Tmax = 0.442h = 88
3592 measured reflectionsk = 1616
3592 independent reflectionsl = 1414
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-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 reflectionsΔρmax = 2.13 e Å3
155 parametersΔρmin = 1.09 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. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Se10.30058 (5)0.38460 (3)0.26380 (3)0.02087 (14)
Se20.22249 (5)0.46181 (3)0.09784 (4)0.02753 (15)
O10.4344 (4)0.3257 (2)0.4280 (2)0.0218 (5)
C10.5087 (5)0.4669 (3)0.2863 (3)0.0191 (7)
C20.5442 (5)0.5374 (3)0.2044 (4)0.0247 (8)
C30.7230 (6)0.5973 (4)0.2160 (4)0.0323 (9)
H3A0.8273760.5623250.1834110.039*
H3B0.7041920.6593070.1776690.039*
C40.7745 (6)0.6170 (3)0.3320 (4)0.0280 (9)
H40.6680970.6540610.3615390.034*
C50.7934 (5)0.5208 (3)0.3957 (4)0.0238 (8)
H5A0.9075640.4861380.3745980.029*
H5B0.8088330.5356510.4727620.029*
C60.6235 (5)0.4562 (3)0.3766 (3)0.0205 (7)
C70.4253 (6)0.5453 (3)0.1185 (4)0.0264 (8)
H70.4453010.5944260.0674420.032*
C80.5745 (6)0.3832 (3)0.4485 (4)0.0255 (8)
H80.6464130.3761730.5136960.031*
C90.9499 (6)0.6780 (3)0.3481 (3)0.0289 (9)
C101.0923 (7)0.6835 (4)0.2759 (4)0.0347 (10)
H101.0860070.6435390.2143140.042*
C111.2429 (6)0.7460 (3)0.2922 (4)0.0290 (9)
H111.3372920.7501650.2412270.035*
C121.2548 (6)0.8022 (3)0.3829 (4)0.0269 (8)
H121.3561550.8463310.3943090.032*
C131.1176 (6)0.7939 (3)0.4576 (4)0.0291 (9)
H131.1267220.8312090.5210620.035*
C140.9679 (6)0.7315 (3)0.4397 (4)0.0284 (8)
H140.8759660.7255660.4918740.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se10.01223 (18)0.0206 (2)0.0299 (3)0.00103 (11)0.00277 (14)0.00151 (14)
Se20.0183 (2)0.0294 (2)0.0341 (3)0.00239 (13)0.00616 (16)0.00050 (16)
O10.0165 (11)0.0265 (13)0.0231 (14)0.0034 (10)0.0078 (9)0.0040 (11)
C10.0153 (15)0.0172 (15)0.0248 (19)0.0004 (11)0.0011 (13)0.0011 (13)
C20.0195 (16)0.0190 (17)0.035 (2)0.0032 (12)0.0042 (15)0.0061 (15)
C30.0239 (19)0.031 (2)0.041 (3)0.0058 (16)0.0055 (17)0.0096 (19)
C40.0230 (18)0.033 (2)0.028 (2)0.0039 (14)0.0005 (15)0.0012 (16)
C50.0157 (16)0.0234 (17)0.032 (2)0.0017 (12)0.0050 (14)0.0019 (15)
C60.0153 (15)0.0179 (16)0.028 (2)0.0025 (11)0.0008 (13)0.0033 (14)
C70.0216 (17)0.0235 (18)0.033 (2)0.0031 (13)0.0068 (15)0.0059 (16)
C80.0215 (17)0.028 (2)0.027 (2)0.0035 (14)0.0032 (14)0.0005 (15)
C90.0229 (18)0.039 (2)0.024 (2)0.0130 (16)0.0013 (14)0.0034 (17)
C100.038 (2)0.040 (2)0.027 (2)0.0219 (19)0.0059 (17)0.0082 (19)
C110.0250 (19)0.033 (2)0.030 (2)0.0155 (16)0.0079 (15)0.0006 (17)
C120.0294 (19)0.0225 (17)0.029 (2)0.0110 (15)0.0028 (15)0.0013 (16)
C130.0283 (19)0.0270 (19)0.032 (2)0.0023 (15)0.0048 (16)0.0062 (17)
C140.0193 (17)0.039 (2)0.027 (2)0.0034 (15)0.0051 (14)0.0034 (17)
Geometric parameters (Å, º) top
Se1—C11.878 (4)C5—H5A0.9900
Se1—O12.375 (3)C5—H5B0.9900
Se1—Se22.3849 (6)C6—C81.409 (6)
Se2—C71.856 (4)C7—H70.9500
O1—C81.292 (5)C8—H80.9500
C1—C61.375 (5)C9—C141.370 (7)
C1—C21.449 (6)C9—C101.392 (6)
C2—C71.344 (6)C10—C111.384 (5)
C2—C31.518 (6)C10—H100.9500
C3—C41.511 (7)C11—C121.380 (6)
C3—H3A0.9900C11—H110.9500
C3—H3B0.9900C12—C131.389 (6)
C4—C91.511 (6)C12—H120.9500
C4—C51.555 (6)C13—C141.380 (6)
C4—H41.0000C13—H130.9500
C5—C61.512 (5)C14—H140.9500
C1—Se1—O178.26 (14)H5A—C5—H5B107.9
C1—Se1—Se290.54 (12)C1—C6—C8116.8 (4)
O1—Se1—Se2168.62 (7)C1—C6—C5120.4 (4)
C7—Se2—Se190.52 (14)C8—C6—C5122.8 (4)
C8—O1—Se1103.6 (2)C2—C7—Se2121.2 (3)
C6—C1—C2122.8 (3)C2—C7—H7119.4
C6—C1—Se1119.5 (3)Se2—C7—H7119.4
C2—C1—Se1117.6 (3)O1—C8—C6121.7 (4)
C7—C2—C1120.0 (4)O1—C8—H8119.1
C7—C2—C3121.7 (4)C6—C8—H8119.1
C1—C2—C3118.2 (4)C14—C9—C10118.4 (4)
C4—C3—C2110.8 (4)C14—C9—C4117.3 (4)
C4—C3—H3A109.5C10—C9—C4124.3 (4)
C2—C3—H3A109.5C11—C10—C9121.2 (4)
C4—C3—H3B109.5C11—C10—H10119.4
C2—C3—H3B109.5C9—C10—H10119.4
H3A—C3—H3B108.1C12—C11—C10119.5 (4)
C3—C4—C9113.0 (4)C12—C11—H11120.3
C3—C4—C5110.7 (4)C10—C11—H11120.3
C9—C4—C5111.0 (3)C11—C12—C13119.5 (4)
C3—C4—H4107.3C11—C12—H12120.2
C9—C4—H4107.3C13—C12—H12120.2
C5—C4—H4107.3C14—C13—C12120.2 (4)
C6—C5—C4112.0 (3)C14—C13—H13119.9
C6—C5—H5A109.2C12—C13—H13119.9
C4—C5—H5A109.2C9—C14—C13121.1 (4)
C6—C5—H5B109.2C9—C14—H14119.5
C4—C5—H5B109.2C13—C14—H14119.5
O1—Se1—C1—C60.9 (3)C4—C5—C6—C8157.9 (4)
Se2—Se1—C1—C6178.9 (3)C1—C2—C7—Se24.0 (6)
O1—Se1—C1—C2177.0 (3)C3—C2—C7—Se2172.8 (3)
Se2—Se1—C1—C20.9 (3)Se1—Se2—C7—C22.6 (4)
C6—C1—C2—C7179.0 (4)Se1—O1—C8—C63.8 (4)
Se1—C1—C2—C73.1 (6)C1—C6—C8—O13.5 (6)
C6—C1—C2—C34.1 (6)C5—C6—C8—O1176.4 (4)
Se1—C1—C2—C3173.8 (3)C3—C4—C9—C14154.4 (4)
C7—C2—C3—C4149.9 (4)C5—C4—C9—C1480.5 (5)
C1—C2—C3—C433.3 (6)C3—C4—C9—C1025.2 (7)
C2—C3—C4—C9179.0 (4)C5—C4—C9—C1099.9 (5)
C2—C3—C4—C555.8 (5)C14—C9—C10—C114.2 (8)
C3—C4—C5—C650.8 (5)C4—C9—C10—C11175.4 (5)
C9—C4—C5—C6177.2 (4)C9—C10—C11—C121.7 (8)
C2—C1—C6—C8178.6 (3)C10—C11—C12—C131.2 (7)
Se1—C1—C6—C80.7 (5)C11—C12—C13—C141.6 (7)
C2—C1—C6—C51.4 (6)C10—C9—C14—C133.9 (7)
Se1—C1—C6—C5179.2 (3)C4—C9—C14—C13175.8 (4)
C4—C5—C6—C122.2 (5)C12—C13—C14—C91.0 (7)
 

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