Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618014833/cu3133sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014833/cu313314sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618014833/cu313315sup3.hkl |
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).
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 |
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 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 |
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. |
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* |
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) |
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) |
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. |
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 |
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 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 |
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. |
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* |
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) |
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) |