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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802013260/tk6070sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802013260/tk6070Isup2.hkl
Contains datablock I

CCDC reference: 193779

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](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
C21H20OSeDx = 1.455 Mg m3
Mr = 367.33Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 8192 reflections
a = 8.1766 (2) Åθ = 2–26°
b = 8.8854 (2) ŵ = 2.24 mm1
c = 23.0888 (3) ÅT = 150 K
V = 1677.46 (4) Å3Irregular fragment, colourless
Z = 40.42 × 0.36 × 0.18 mm
F(000) = 752
Data collection top
Siemens SMART
diffractometer
3416 independent reflections
Radiation source: fine-focus sealed tube3227 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Area–detector ω scansθmax = 26.4°, θmin = 1.8°
Absorption correction: multi-scan
(Blessing, 1995)
h = 1010
Tmin = 0.439, Tmax = 0.667k = 011
10162 measured reflectionsl = 028
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026H-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 reflectionsΔρmax = 0.48 e Å3
212 parametersΔρmin = 0.48 e Å3
0 restraintsAbsolute structure: Flack (1983), 0000 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.013 (8)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Se0.53216 (3)0.45318 (3)0.991097 (10)0.02935 (8)
O10.0954 (2)0.5363 (2)1.08227 (6)0.0303 (4)
C20.2269 (3)0.5608 (3)1.04185 (9)0.0249 (5)
H2A0.29310.64921.05480.030*
C30.3368 (3)0.4208 (2)1.04006 (10)0.0243 (5)
H3A0.27300.33311.02500.029*
C40.4022 (3)0.3847 (3)1.10083 (10)0.0287 (5)
H4A0.46210.28791.10000.034*
H4B0.47950.46431.11310.034*
C50.2610 (3)0.3748 (3)1.14411 (10)0.0345 (6)
H5A0.19420.28441.13580.041*
H5B0.30500.36521.18390.041*
C60.1561 (3)0.5133 (3)1.13998 (10)0.0345 (6)
H6A0.06260.50371.16700.041*
H6B0.22100.60221.15190.041*
C1'0.2158 (3)0.7046 (3)0.94898 (10)0.0244 (5)
H1C0.304 (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)
H3C0.03320.43740.98820.033*
C4'0.0494 (3)0.5360 (3)0.90961 (10)0.0307 (5)
H4C0.14120.47910.89710.037*
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)
H5C0.12890.61510.80060.043*
C6'0.0337 (4)0.7746 (3)0.77958 (10)0.0397 (6)
H6C0.00780.79120.74170.048*
C7'0.1699 (4)0.8577 (3)0.79936 (12)0.0403 (6)
H7C0.22170.92770.77420.048*
C8'0.2280 (3)0.8379 (3)0.85465 (11)0.0340 (6)
H8C0.31760.89660.86790.041*
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)
H2D0.32390.22880.92720.037*
C3"0.3111 (3)0.2780 (3)0.84111 (11)0.0353 (6)
H3D0.24350.19520.83090.042*
C4"0.3631 (4)0.3777 (4)0.79867 (12)0.0401 (6)
H4D0.33330.36160.75940.048*
C5"0.4573 (4)0.4996 (3)0.81336 (11)0.0393 (6)
H5D0.49230.56800.78430.047*
C6"0.5020 (3)0.5233 (3)0.87088 (11)0.0328 (6)
H6D0.56600.60850.88110.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se0.01600 (12)0.03938 (13)0.03267 (13)0.00077 (9)0.00343 (9)0.00461 (10)
O10.0228 (8)0.0476 (10)0.0204 (8)0.0049 (8)0.0007 (6)0.0017 (8)
C20.0200 (11)0.0305 (12)0.0241 (11)0.0010 (10)0.0012 (8)0.0031 (10)
C30.0195 (11)0.0279 (12)0.0254 (12)0.0004 (9)0.0030 (9)0.0017 (9)
C40.0238 (12)0.0325 (12)0.0298 (13)0.0010 (10)0.0088 (10)0.0028 (10)
C50.0318 (14)0.0466 (15)0.0251 (12)0.0039 (12)0.0077 (10)0.0075 (11)
C60.0325 (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—C31.978 (2)C4'—H4C0.9500
O1—C21.440 (3)C4A'—C5'1.424 (3)
O1—C61.436 (3)C4A'—C8A'1.426 (3)
C2—C2'1.516 (3)C5'—C6'1.359 (4)
C2—C31.535 (3)C5'—H5C0.9500
C2—H2A1.0000C6'—C7'1.412 (5)
C3—C41.535 (3)C6'—H6C0.9500
C3—H3A1.0000C7'—C8'1.373 (4)
C4—C51.529 (4)C7'—H7C0.9500
C4—H4A0.9900C8'—C8A'1.416 (3)
C4—H4B0.9900C8'—H8C0.9500
C5—C61.504 (4)C1"—C2"1.388 (3)
C5—H5A0.9900C1"—C6"1.391 (3)
C5—H5B0.9900C2"—C3"1.387 (4)
C6—H6A0.9900C2"—H2D0.9500
C6—H6B0.9900C3"—C4"1.388 (4)
C1'—C2'1.366 (3)C3"—H3D0.9500
C1'—C8A'1.423 (3)C4"—C5"1.372 (4)
C1'—H1C0.93 (3)C4"—H4D0.9500
C2'—C3'1.415 (3)C5"—C6"1.393 (4)
C3'—C4'1.372 (3)C5"—H5D0.9500
C3'—H3C0.9500C6"—H6D0.9500
C1"—Se—C3103.81 (10)C8A'—C8'—H8C119.7
C2—O1—C6111.39 (18)C8'—C8A'—C1'121.8 (2)
O1—C2—C2'107.06 (17)C8'—C8A'—C4A'119.2 (2)
O1—C2—C3109.40 (18)C1'—C8A'—C4A'118.9 (2)
C2'—C2—C3112.84 (17)C2"—C1"—C6"119.8 (2)
O1—C2—H2A109.2C2"—C1"—Se122.37 (18)
C2'—C2—H2A109.2C6"—C1"—Se117.73 (18)
C3—C2—H2A109.2C3"—C2"—C1"119.7 (2)
C2—C3—C4110.40 (19)C3"—C2"—H2D120.1
C2—C3—Se111.73 (14)C1"—C2"—H2D120.1
C4—C3—Se105.73 (16)C2"—C3"—C4"120.3 (3)
C2—C3—H3A109.6C2"—C3"—H3D119.8
C4—C3—H3A109.6C4"—C3"—H3D119.8
Se—C3—H3A109.6C5"—C4"—C3"120.1 (3)
C5—C4—C3110.2 (2)C5"—C4"—H4D120.0
C5—C4—H4A109.6C3"—C4"—H4D120.0
C3—C4—H4A109.6C4"—C5"—C6"120.2 (2)
C5—C4—H4B109.6C4"—C5"—H5D119.9
C3—C4—H4B109.6C6"—C5"—H5D119.9
H4A—C4—H4B108.1C1"—C6"—C5"119.9 (2)
C6—C5—C4110.0 (2)C1"—C6"—H6D120.0
C6—C5—H5A109.7C5"—C6"—H6D120.0
C4—C5—H5A109.7C1"—Se—C3103.81 (10)
C6—C5—H5B109.7C2—O1—C6111.39 (18)
C4—C5—H5B109.7O1—C2—C2'107.06 (17)
H5A—C5—H5B108.2O1—C2—C3109.40 (18)
O1—C6—C5111.9 (2)C2'—C2—C3112.84 (17)
O1—C6—H6A109.2C2—C3—C4110.40 (19)
C5—C6—H6A109.2C2—C3—Se111.73 (14)
O1—C6—H6B109.2C4—C3—Se105.73 (16)
C5—C6—H6B109.2C5—C4—C3110.2 (2)
H6A—C6—H6B107.9C6—C5—C4110.0 (2)
C2'—C1'—C8A'121.3 (2)O1—C6—C5111.9 (2)
C2'—C1'—H1C122.5 (16)C2'—C1'—C8A'121.3 (2)
C8A'—C1'—H1C116.2 (16)C1'—C2'—C3'119.5 (2)
C1'—C2'—C3'119.5 (2)C1'—C2'—C2120.1 (2)
C1'—C2'—C2120.1 (2)C3'—C2'—C2120.3 (2)
C3'—C2'—C2120.3 (2)C4'—C3'—C2'120.6 (2)
C4'—C3'—C2'120.6 (2)C3'—C4'—C4A'121.1 (2)
C4'—C3'—H3C119.7C4'—C4A'—C5'123.4 (2)
C2'—C3'—H3C119.7C4'—C4A'—C8A'118.4 (2)
C3'—C4'—C4A'121.1 (2)C5'—C4A'—C8A'118.2 (2)
C3'—C4'—H4C119.5C6'—C5'—C4A'121.4 (3)
C4A'—C4'—H4C119.5C5'—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'—H5C119.3C1'—C8A'—C4A'118.9 (2)
C4A'—C5'—H5C119.3C2"—C1"—C6"119.8 (2)
C5'—C6'—C7'120.1 (2)C2"—C1"—Se122.37 (18)
C5'—C6'—H6C119.9C6"—C1"—Se117.73 (18)
C7'—C6'—H6C119.9C3"—C2"—C1"119.7 (2)
C8'—C7'—C6'120.4 (3)C2"—C3"—C4"120.3 (3)
C8'—C7'—H7C119.8C5"—C4"—C3"120.1 (3)
C6'—C7'—H7C119.8C4"—C5"—C6"120.2 (2)
C7'—C8'—C8A'120.5 (3)C1"—C6"—C5"119.9 (2)
C7'—C8'—H8C119.7
C6—O1—C2—C2'175.51 (19)C4'—C4A'—C5'—C6'178.7 (2)
C6—O1—C2—C361.9 (2)C8A'—C4A'—C5'—C6'0.4 (3)
O1—C2—C3—C457.2 (2)C4A'—C5'—C6'—C7'0.8 (4)
C2'—C2—C3—C4176.2 (2)C5'—C6'—C7'—C8'1.9 (4)
O1—C2—C3—Se174.55 (14)C6'—C7'—C8'—C8A'1.9 (4)
C2'—C2—C3—Se66.4 (2)C7'—C8'—C8A'—C1'178.0 (2)
C1"—Se—C3—C280.82 (16)C7'—C8'—C8A'—C4A'0.7 (4)
C1"—Se—C3—C4159.04 (15)C2'—C1'—C8A'—C8'176.9 (2)
C2—C3—C4—C552.7 (3)C2'—C1'—C8A'—C4A'1.9 (3)
Se—C3—C4—C5173.71 (17)C4'—C4A'—C8A'—C8'178.7 (2)
C3—C4—C5—C651.7 (3)C5'—C4A'—C8A'—C8'0.5 (3)
C2—O1—C6—C562.6 (3)C4'—C4A'—C8A'—C1'0.0 (3)
C4—C5—C6—O156.5 (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'—C2174.2 (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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