trans-2-(2-Naphthyl)-3-(phenyl­selenyl)­tetra­hydro­pyran

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.

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

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

Crystal data

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) Å^3	Irregular fragment, colourless
Z = 4	0.42 × 0.36 × 0.18 mm
F(000) = 752

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	H-atom parameters constrained
wR(F^2) = 0.065	w = 1/[σ^2(Fo^2) + (0.0366P)^2] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)