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organic compounds
The crystal structure of the title compound, C21H20OSe, has established the absolute configuration and shows that the tetrahydrofuran ring adopts a chair conformation, with both the phenylselenyl and naphthyl substituents occupying equatorial positions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802013260/tk6070sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802013260/tk6070Isup2.hkl |
CCDC reference: 193779
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.004 Å
- R factor = 0.026
- wR factor = 0.065
- Data-to-parameter ratio = 16.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.40 From the CIF: _reflns_number_total 3416 Count of symmetry unique reflns 1994 Completeness (_total/calc) 171.31% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1422 Fraction of Friedel pairs measured 0.713 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
Computing details top
Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS Sheldrick, (1990); program(s) used to refine structure: SHELXL97 Sheldrick, (1997); molecular graphics: SHELXTL (Siemens, 1994); software used to prepare material for publication: SHELXL97.
trans-2-(2-Naphthyl)-3-(phenylselenyl)tetrahydropyran top
Crystal data top
C21H20OSe | Dx = 1.455 Mg m−3 |
Mr = 367.33 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 8192 reflections |
a = 8.1766 (2) Å | θ = 2–26° |
b = 8.8854 (2) Å | µ = 2.24 mm−1 |
c = 23.0888 (3) Å | T = 150 K |
V = 1677.46 (4) Å3 | Irregular fragment, colourless |
Z = 4 | 0.42 × 0.36 × 0.18 mm |
F(000) = 752 |
Data collection top
Siemens SMART diffractometer | 3416 independent reflections |
Radiation source: fine-focus sealed tube | 3227 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Area–detector ω scans | θmax = 26.4°, θmin = 1.8° |
Absorption correction: multi-scan (Blessing, 1995) | h = −10→10 |
Tmin = 0.439, Tmax = 0.667 | k = 0→11 |
10162 measured reflections | l = 0→28 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.026 | H-atom parameters constrained |
wR(F2) = 0.065 | w = 1/[σ2(Fo2) + (0.0366P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.009 |
3416 reflections | Δρmax = 0.48 e Å−3 |
212 parameters | Δρmin = −0.48 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 0000 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.013 (8) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Se | 0.53216 (3) | 0.45318 (3) | 0.991097 (10) | 0.02935 (8) | |
O1 | 0.0954 (2) | 0.5363 (2) | 1.08227 (6) | 0.0303 (4) | |
C2 | 0.2269 (3) | 0.5608 (3) | 1.04185 (9) | 0.0249 (5) | |
H2A | 0.2931 | 0.6492 | 1.0548 | 0.030* | |
C3 | 0.3368 (3) | 0.4208 (2) | 1.04006 (10) | 0.0243 (5) | |
H3A | 0.2730 | 0.3331 | 1.0250 | 0.029* | |
C4 | 0.4022 (3) | 0.3847 (3) | 1.10083 (10) | 0.0287 (5) | |
H4A | 0.4621 | 0.2879 | 1.1000 | 0.034* | |
H4B | 0.4795 | 0.4643 | 1.1131 | 0.034* | |
C5 | 0.2610 (3) | 0.3748 (3) | 1.14411 (10) | 0.0345 (6) | |
H5A | 0.1942 | 0.2844 | 1.1358 | 0.041* | |
H5B | 0.3050 | 0.3652 | 1.1839 | 0.041* | |
C6 | 0.1561 (3) | 0.5133 (3) | 1.13998 (10) | 0.0345 (6) | |
H6A | 0.0626 | 0.5037 | 1.1670 | 0.041* | |
H6B | 0.2210 | 0.6022 | 1.1519 | 0.041* | |
C1' | 0.2158 (3) | 0.7046 (3) | 0.94898 (10) | 0.0244 (5) | |
H1C | 0.304 (4) | 0.764 (3) | 0.9606 (11) | 0.029* | |
C2' | 0.1496 (3) | 0.5961 (2) | 0.98376 (10) | 0.0224 (5) | |
C3' | 0.0142 (3) | 0.5117 (2) | 0.96380 (10) | 0.0272 (5) | |
H3C | −0.0332 | 0.4374 | 0.9882 | 0.033* | |
C4' | −0.0494 (3) | 0.5360 (3) | 0.90961 (10) | 0.0307 (5) | |
H4C | −0.1412 | 0.4791 | 0.8971 | 0.037* | |
C4A' | 0.0196 (3) | 0.6447 (3) | 0.87196 (9) | 0.0263 (5) | |
C5' | −0.0381 (4) | 0.6711 (3) | 0.81465 (10) | 0.0360 (6) | |
H5C | −0.1289 | 0.6151 | 0.8006 | 0.043* | |
C6' | 0.0337 (4) | 0.7746 (3) | 0.77958 (10) | 0.0397 (6) | |
H6C | −0.0078 | 0.7912 | 0.7417 | 0.048* | |
C7' | 0.1699 (4) | 0.8577 (3) | 0.79936 (12) | 0.0403 (6) | |
H7C | 0.2217 | 0.9277 | 0.7742 | 0.048* | |
C8' | 0.2280 (3) | 0.8379 (3) | 0.85465 (11) | 0.0340 (6) | |
H8C | 0.3176 | 0.8966 | 0.8679 | 0.041* | |
C8A' | 0.1553 (3) | 0.7309 (3) | 0.89209 (10) | 0.0245 (5) | |
C1" | 0.4527 (3) | 0.4219 (2) | 0.91339 (9) | 0.0260 (5) | |
C2" | 0.3573 (3) | 0.2987 (3) | 0.89836 (11) | 0.0306 (5) | |
H2D | 0.3239 | 0.2288 | 0.9272 | 0.037* | |
C3" | 0.3111 (3) | 0.2780 (3) | 0.84111 (11) | 0.0353 (6) | |
H3D | 0.2435 | 0.1952 | 0.8309 | 0.042* | |
C4" | 0.3631 (4) | 0.3777 (4) | 0.79867 (12) | 0.0401 (6) | |
H4D | 0.3333 | 0.3616 | 0.7594 | 0.048* | |
C5" | 0.4573 (4) | 0.4996 (3) | 0.81336 (11) | 0.0393 (6) | |
H5D | 0.4923 | 0.5680 | 0.7843 | 0.047* | |
C6" | 0.5020 (3) | 0.5233 (3) | 0.87088 (11) | 0.0328 (6) | |
H6D | 0.5660 | 0.6085 | 0.8811 | 0.039* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Se | 0.01600 (12) | 0.03938 (13) | 0.03267 (13) | 0.00077 (9) | −0.00343 (9) | −0.00461 (10) |
O1 | 0.0228 (8) | 0.0476 (10) | 0.0204 (8) | 0.0049 (8) | 0.0007 (6) | 0.0017 (8) |
C2 | 0.0200 (11) | 0.0305 (12) | 0.0241 (11) | 0.0010 (10) | −0.0012 (8) | −0.0031 (10) |
C3 | 0.0195 (11) | 0.0279 (12) | 0.0254 (12) | 0.0004 (9) | −0.0030 (9) | −0.0017 (9) |
C4 | 0.0238 (12) | 0.0325 (12) | 0.0298 (13) | −0.0010 (10) | −0.0088 (10) | 0.0028 (10) |
C5 | 0.0318 (14) | 0.0466 (15) | 0.0251 (12) | −0.0039 (12) | −0.0077 (10) | 0.0075 (11) |
C6 | 0.0325 (14) | 0.0518 (16) | 0.0193 (12) | 0.0015 (11) | −0.0032 (10) | −0.0003 (10) |
C1' | 0.0169 (12) | 0.0285 (12) | 0.0279 (12) | 0.0049 (9) | −0.0030 (9) | −0.0045 (9) |
C2' | 0.0165 (10) | 0.0270 (11) | 0.0236 (11) | 0.0057 (8) | −0.0019 (9) | −0.0040 (9) |
C3' | 0.0218 (12) | 0.0304 (11) | 0.0294 (12) | −0.0004 (9) | 0.0000 (9) | −0.0002 (8) |
C4' | 0.0217 (12) | 0.0339 (12) | 0.0365 (12) | −0.0006 (12) | −0.0061 (10) | −0.0074 (11) |
C4A' | 0.0213 (12) | 0.0332 (11) | 0.0244 (11) | 0.0090 (10) | −0.0034 (9) | −0.0050 (8) |
C5' | 0.0297 (13) | 0.0482 (15) | 0.0301 (13) | 0.0110 (13) | −0.0088 (12) | −0.0102 (10) |
C6' | 0.0377 (15) | 0.0614 (17) | 0.0201 (11) | 0.0203 (15) | −0.0024 (12) | −0.0005 (10) |
C7' | 0.0356 (16) | 0.0508 (16) | 0.0344 (14) | 0.0113 (13) | 0.0074 (12) | 0.0117 (13) |
C8' | 0.0267 (13) | 0.0405 (15) | 0.0348 (14) | 0.0032 (11) | 0.0000 (11) | 0.0044 (11) |
C8A' | 0.0197 (12) | 0.0286 (12) | 0.0251 (12) | 0.0072 (9) | −0.0003 (9) | −0.0023 (9) |
C1" | 0.0189 (11) | 0.0330 (12) | 0.0262 (11) | 0.0063 (10) | 0.0015 (10) | −0.0017 (8) |
C2" | 0.0252 (13) | 0.0376 (14) | 0.0290 (13) | −0.0016 (10) | 0.0010 (10) | 0.0002 (11) |
C3" | 0.0283 (15) | 0.0451 (16) | 0.0325 (14) | −0.0027 (11) | −0.0022 (11) | −0.0041 (11) |
C4" | 0.0341 (16) | 0.0602 (18) | 0.0260 (13) | 0.0072 (14) | 0.0012 (11) | −0.0004 (13) |
C5" | 0.0347 (14) | 0.0491 (15) | 0.0342 (13) | 0.0037 (12) | 0.0096 (12) | 0.0092 (10) |
C6" | 0.0247 (14) | 0.0322 (13) | 0.0413 (14) | 0.0026 (10) | 0.0059 (9) | 0.0006 (10) |
Geometric parameters (Å, º) top
Se—C1" | 1.928 (2) | C4'—C4A' | 1.417 (3) |
Se—C3 | 1.978 (2) | C4'—H4C | 0.9500 |
O1—C2 | 1.440 (3) | C4A'—C5' | 1.424 (3) |
O1—C6 | 1.436 (3) | C4A'—C8A' | 1.426 (3) |
C2—C2' | 1.516 (3) | C5'—C6' | 1.359 (4) |
C2—C3 | 1.535 (3) | C5'—H5C | 0.9500 |
C2—H2A | 1.0000 | C6'—C7' | 1.412 (5) |
C3—C4 | 1.535 (3) | C6'—H6C | 0.9500 |
C3—H3A | 1.0000 | C7'—C8' | 1.373 (4) |
C4—C5 | 1.529 (4) | C7'—H7C | 0.9500 |
C4—H4A | 0.9900 | C8'—C8A' | 1.416 (3) |
C4—H4B | 0.9900 | C8'—H8C | 0.9500 |
C5—C6 | 1.504 (4) | C1"—C2" | 1.388 (3) |
C5—H5A | 0.9900 | C1"—C6" | 1.391 (3) |
C5—H5B | 0.9900 | C2"—C3" | 1.387 (4) |
C6—H6A | 0.9900 | C2"—H2D | 0.9500 |
C6—H6B | 0.9900 | C3"—C4" | 1.388 (4) |
C1'—C2' | 1.366 (3) | C3"—H3D | 0.9500 |
C1'—C8A' | 1.423 (3) | C4"—C5" | 1.372 (4) |
C1'—H1C | 0.93 (3) | C4"—H4D | 0.9500 |
C2'—C3' | 1.415 (3) | C5"—C6" | 1.393 (4) |
C3'—C4' | 1.372 (3) | C5"—H5D | 0.9500 |
C3'—H3C | 0.9500 | C6"—H6D | 0.9500 |
C1"—Se—C3 | 103.81 (10) | C8A'—C8'—H8C | 119.7 |
C2—O1—C6 | 111.39 (18) | C8'—C8A'—C1' | 121.8 (2) |
O1—C2—C2' | 107.06 (17) | C8'—C8A'—C4A' | 119.2 (2) |
O1—C2—C3 | 109.40 (18) | C1'—C8A'—C4A' | 118.9 (2) |
C2'—C2—C3 | 112.84 (17) | C2"—C1"—C6" | 119.8 (2) |
O1—C2—H2A | 109.2 | C2"—C1"—Se | 122.37 (18) |
C2'—C2—H2A | 109.2 | C6"—C1"—Se | 117.73 (18) |
C3—C2—H2A | 109.2 | C3"—C2"—C1" | 119.7 (2) |
C2—C3—C4 | 110.40 (19) | C3"—C2"—H2D | 120.1 |
C2—C3—Se | 111.73 (14) | C1"—C2"—H2D | 120.1 |
C4—C3—Se | 105.73 (16) | C2"—C3"—C4" | 120.3 (3) |
C2—C3—H3A | 109.6 | C2"—C3"—H3D | 119.8 |
C4—C3—H3A | 109.6 | C4"—C3"—H3D | 119.8 |
Se—C3—H3A | 109.6 | C5"—C4"—C3" | 120.1 (3) |
C5—C4—C3 | 110.2 (2) | C5"—C4"—H4D | 120.0 |
C5—C4—H4A | 109.6 | C3"—C4"—H4D | 120.0 |
C3—C4—H4A | 109.6 | C4"—C5"—C6" | 120.2 (2) |
C5—C4—H4B | 109.6 | C4"—C5"—H5D | 119.9 |
C3—C4—H4B | 109.6 | C6"—C5"—H5D | 119.9 |
H4A—C4—H4B | 108.1 | C1"—C6"—C5" | 119.9 (2) |
C6—C5—C4 | 110.0 (2) | C1"—C6"—H6D | 120.0 |
C6—C5—H5A | 109.7 | C5"—C6"—H6D | 120.0 |
C4—C5—H5A | 109.7 | C1"—Se—C3 | 103.81 (10) |
C6—C5—H5B | 109.7 | C2—O1—C6 | 111.39 (18) |
C4—C5—H5B | 109.7 | O1—C2—C2' | 107.06 (17) |
H5A—C5—H5B | 108.2 | O1—C2—C3 | 109.40 (18) |
O1—C6—C5 | 111.9 (2) | C2'—C2—C3 | 112.84 (17) |
O1—C6—H6A | 109.2 | C2—C3—C4 | 110.40 (19) |
C5—C6—H6A | 109.2 | C2—C3—Se | 111.73 (14) |
O1—C6—H6B | 109.2 | C4—C3—Se | 105.73 (16) |
C5—C6—H6B | 109.2 | C5—C4—C3 | 110.2 (2) |
H6A—C6—H6B | 107.9 | C6—C5—C4 | 110.0 (2) |
C2'—C1'—C8A' | 121.3 (2) | O1—C6—C5 | 111.9 (2) |
C2'—C1'—H1C | 122.5 (16) | C2'—C1'—C8A' | 121.3 (2) |
C8A'—C1'—H1C | 116.2 (16) | C1'—C2'—C3' | 119.5 (2) |
C1'—C2'—C3' | 119.5 (2) | C1'—C2'—C2 | 120.1 (2) |
C1'—C2'—C2 | 120.1 (2) | C3'—C2'—C2 | 120.3 (2) |
C3'—C2'—C2 | 120.3 (2) | C4'—C3'—C2' | 120.6 (2) |
C4'—C3'—C2' | 120.6 (2) | C3'—C4'—C4A' | 121.1 (2) |
C4'—C3'—H3C | 119.7 | C4'—C4A'—C5' | 123.4 (2) |
C2'—C3'—H3C | 119.7 | C4'—C4A'—C8A' | 118.4 (2) |
C3'—C4'—C4A' | 121.1 (2) | C5'—C4A'—C8A' | 118.2 (2) |
C3'—C4'—H4C | 119.5 | C6'—C5'—C4A' | 121.4 (3) |
C4A'—C4'—H4C | 119.5 | C5'—C6'—C7' | 120.1 (2) |
C4'—C4A'—C5' | 123.4 (2) | C8'—C7'—C6' | 120.4 (3) |
C4'—C4A'—C8A' | 118.4 (2) | C7'—C8'—C8A' | 120.5 (3) |
C5'—C4A'—C8A' | 118.2 (2) | C8'—C8A'—C1' | 121.8 (2) |
C6'—C5'—C4A' | 121.4 (3) | C8'—C8A'—C4A' | 119.2 (2) |
C6'—C5'—H5C | 119.3 | C1'—C8A'—C4A' | 118.9 (2) |
C4A'—C5'—H5C | 119.3 | C2"—C1"—C6" | 119.8 (2) |
C5'—C6'—C7' | 120.1 (2) | C2"—C1"—Se | 122.37 (18) |
C5'—C6'—H6C | 119.9 | C6"—C1"—Se | 117.73 (18) |
C7'—C6'—H6C | 119.9 | C3"—C2"—C1" | 119.7 (2) |
C8'—C7'—C6' | 120.4 (3) | C2"—C3"—C4" | 120.3 (3) |
C8'—C7'—H7C | 119.8 | C5"—C4"—C3" | 120.1 (3) |
C6'—C7'—H7C | 119.8 | C4"—C5"—C6" | 120.2 (2) |
C7'—C8'—C8A' | 120.5 (3) | C1"—C6"—C5" | 119.9 (2) |
C7'—C8'—H8C | 119.7 | ||
C6—O1—C2—C2' | −175.51 (19) | C4'—C4A'—C5'—C6' | −178.7 (2) |
C6—O1—C2—C3 | 61.9 (2) | C8A'—C4A'—C5'—C6' | 0.4 (3) |
O1—C2—C3—C4 | −57.2 (2) | C4A'—C5'—C6'—C7' | 0.8 (4) |
C2'—C2—C3—C4 | −176.2 (2) | C5'—C6'—C7'—C8' | −1.9 (4) |
O1—C2—C3—Se | −174.55 (14) | C6'—C7'—C8'—C8A' | 1.9 (4) |
C2'—C2—C3—Se | 66.4 (2) | C7'—C8'—C8A'—C1' | 178.0 (2) |
C1"—Se—C3—C2 | −80.82 (16) | C7'—C8'—C8A'—C4A' | −0.7 (4) |
C1"—Se—C3—C4 | 159.04 (15) | C2'—C1'—C8A'—C8' | −176.9 (2) |
C2—C3—C4—C5 | 52.7 (3) | C2'—C1'—C8A'—C4A' | 1.9 (3) |
Se—C3—C4—C5 | 173.71 (17) | C4'—C4A'—C8A'—C8' | 178.7 (2) |
C3—C4—C5—C6 | −51.7 (3) | C5'—C4A'—C8A'—C8' | −0.5 (3) |
C2—O1—C6—C5 | −62.6 (3) | C4'—C4A'—C8A'—C1' | 0.0 (3) |
C4—C5—C6—O1 | 56.5 (3) | C5'—C4A'—C8A'—C1' | −179.2 (2) |
C8A'—C1'—C2'—C3' | −2.4 (3) | C3—Se—C1"—C2" | −47.6 (2) |
C8A'—C1'—C2'—C2 | 174.2 (2) | C3—Se—C1"—C6" | 136.17 (18) |
O1—C2—C2'—C1' | 140.2 (2) | C6"—C1"—C2"—C3" | −0.4 (4) |
C3—C2—C2'—C1' | −99.4 (2) | Se—C1"—C2"—C3" | −176.6 (2) |
O1—C2—C2'—C3' | −43.2 (3) | C1"—C2"—C3"—C4" | 1.6 (4) |
C3—C2—C2'—C3' | 77.2 (2) | C2"—C3"—C4"—C5" | −1.6 (4) |
C1'—C2'—C3'—C4' | 1.1 (3) | C3"—C4"—C5"—C6" | 0.3 (4) |
C2—C2'—C3'—C4' | −175.5 (2) | C2"—C1"—C6"—C5" | −0.8 (4) |
C2'—C3'—C4'—C4A' | 0.8 (3) | Se—C1"—C6"—C5" | 175.5 (2) |
C3'—C4'—C4A'—C5' | 177.9 (2) | C4"—C5"—C6"—C1" | 0.9 (4) |
C3'—C4'—C4A'—C8A' | −1.2 (3) |
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