cis-2-(2-Methoxy­phenyl)-3-(phenyl­selenyl)­tetra­hydro­pyran

The crystal structure of the title compound, C₁₈H₂₀O₂Se, shows that the tetrahydrofuran ring adopts a chair conformation, with the phenyl­selenyl group occupying an axial position and the 2-methoxy­phenyl group in an equatorial position.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.019
• wR factor = 0.052
• Data-to-parameter ratio = 15.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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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.

cis-2-(2-Methoxyphenyl)-3-(phenylselenyl)tetrahydropyran

Crystal data

C18H20O2Se	Z = 2
Mr = 347.30	F(000) = 356
Triclinic, P1	Dx = 1.515 Mg m^−3
a = 7.1823 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.7739 (4) Å	Cell parameters from 6450 reflections
c = 13.9367 (7) Å	θ = 2–26°
α = 97.180 (2)°	µ = 2.47 mm^−1
β = 97.654 (2)°	T = 150 K
γ = 94.793 (2)°	Irregular fragment, yellow
V = 761.18 (7) Å^3	0.36 × 0.28 × 0.14 mm

Data collection

Siemens SMART diffractometer	2984 independent reflections
Radiation source: fine-focus sealed tube	2832 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
Area–detector ω scans	θmax = 26.1°, θmin = 1.5°
Absorption correction: multi-scan (Blessing, 1995)	h = −8→8
Tmin = 0.460, Tmax = 0.709	k = −9→9
7048 measured reflections	l = 0→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.019	Hydrogen site location: difference Fourier map
wR(F^2) = 0.052	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0303P)^2 + 0.2068P] where P = (Fo^2 + 2Fc^2)/3
2984 reflections	(Δ/σ)max = 0.007
193 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se	0.06350 (2)	0.534651 (18)	0.203666 (10)	0.01788 (6)
O1	−0.07940 (15)	0.91423 (15)	0.24290 (8)	0.0206 (2)
C2	0.0635 (2)	0.87059 (19)	0.31477 (10)	0.0165 (3)
H2	0.1363	0.9820	0.3483	0.020*
C3	0.2028 (2)	0.76066 (19)	0.26609 (10)	0.0162 (3)
H3	0.3053	0.7383	0.3176	0.019*
C4	0.2906 (2)	0.8619 (2)	0.19316 (11)	0.0205 (3)
H4	0.3739 (12)	0.9581 (13)	0.2280 (5)	0.025*
H4A	0.3632 (11)	0.7879 (10)	0.1566 (5)	0.025*
C5	0.1403 (2)	0.9289 (2)	0.12311 (11)	0.0233 (3)
H5	0.2008 (9)	1.0089 (11)	0.0853 (6)	0.028*
H5A	0.0724 (10)	0.8313 (14)	0.0776 (7)	0.028*
C6	0.0020 (3)	1.0220 (2)	0.17917 (12)	0.0256 (3)
H6	0.0678 (10)	1.1294 (16)	0.2183 (6)	0.031*
H6A	−0.0995 (15)	1.0553 (6)	0.1325 (7)	0.031*
O2	0.25985 (15)	0.84935 (15)	0.49284 (8)	0.0226 (2)
C1'	0.0743 (2)	0.78189 (19)	0.48253 (10)	0.0174 (3)
C2'	−0.0311 (2)	0.78706 (19)	0.39071 (10)	0.0165 (3)
C3'	−0.2203 (2)	0.7213 (2)	0.37402 (11)	0.0199 (3)
H3B	−0.2931	0.7237	0.3122	0.024*
C4'	−0.3043 (2)	0.6516 (2)	0.44729 (12)	0.0231 (3)
H4B	−0.4339	0.6076	0.4354	0.028*
C5'	−0.1986 (2)	0.6468 (2)	0.53695 (11)	0.0231 (3)
H5B	−0.2559	0.5989	0.5866	0.028*
C6'	−0.0087 (2)	0.7113 (2)	0.55539 (11)	0.0206 (3)
H6B	0.0636	0.7072	0.6172	0.025*
C7'	0.3694 (2)	0.8605 (2)	0.58719 (11)	0.0250 (3)
H7A	0.3083	0.9292	0.6356	0.038*
H7B	0.4961	0.9168	0.5860	0.038*
H7C	0.3789	0.7430	0.6048	0.038*
C1"	0.2638 (2)	0.43192 (19)	0.14563 (11)	0.0171 (3)
C2"	0.2418 (2)	0.3869 (2)	0.04492 (11)	0.0212 (3)
H2C	0.1343	0.4169	0.0054	0.025*
C3"	0.3760 (3)	0.2982 (2)	0.00151 (12)	0.0261 (4)
H3C	0.3584	0.2655	−0.0673	0.031*
C4"	0.5356 (2)	0.2573 (2)	0.05848 (12)	0.0272 (4)
H4C	0.6274	0.1967	0.0289	0.033*
C5"	0.5600 (2)	0.3058 (2)	0.15928 (12)	0.0270 (4)
H5C	0.6703	0.2804	0.1985	0.032*
C6"	0.4247 (2)	0.3907 (2)	0.20269 (11)	0.0231 (3)
H6C	0.4411	0.4212	0.2717	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se	0.01788 (9)	0.01570 (9)	0.02020 (9)	0.00116 (6)	0.00538 (6)	0.00063 (6)
O1	0.0213 (5)	0.0235 (6)	0.0196 (5)	0.0068 (5)	0.0045 (4)	0.0088 (4)
C2	0.0186 (7)	0.0150 (7)	0.0159 (7)	0.0022 (6)	0.0027 (6)	0.0016 (5)
C3	0.0169 (7)	0.0154 (7)	0.0155 (7)	0.0001 (6)	0.0022 (5)	0.0011 (5)
C4	0.0210 (8)	0.0197 (8)	0.0212 (7)	−0.0020 (6)	0.0073 (6)	0.0021 (6)
C5	0.0318 (9)	0.0210 (8)	0.0192 (7)	0.0012 (7)	0.0082 (6)	0.0071 (6)
C6	0.0337 (9)	0.0221 (8)	0.0250 (8)	0.0075 (7)	0.0082 (7)	0.0115 (6)
O2	0.0181 (5)	0.0319 (6)	0.0168 (5)	−0.0004 (5)	0.0010 (4)	0.0033 (4)
C1'	0.0180 (7)	0.0161 (7)	0.0181 (7)	0.0029 (6)	0.0045 (6)	−0.0004 (6)
C2'	0.0199 (7)	0.0140 (7)	0.0163 (7)	0.0042 (6)	0.0054 (6)	0.0006 (5)
C3'	0.0203 (8)	0.0196 (8)	0.0193 (7)	0.0028 (6)	0.0033 (6)	0.0002 (6)
C4'	0.0195 (8)	0.0221 (8)	0.0278 (8)	−0.0003 (6)	0.0078 (6)	0.0004 (6)
C5'	0.0290 (8)	0.0208 (8)	0.0225 (8)	0.0030 (7)	0.0136 (6)	0.0046 (6)
C6'	0.0252 (8)	0.0217 (8)	0.0161 (7)	0.0061 (6)	0.0054 (6)	0.0023 (6)
C7'	0.0224 (8)	0.0320 (9)	0.0192 (7)	0.0054 (7)	−0.0017 (6)	0.0007 (6)
C1"	0.0199 (7)	0.0134 (7)	0.0188 (7)	0.0016 (6)	0.0057 (6)	0.0028 (5)
C2"	0.0246 (8)	0.0210 (8)	0.0181 (7)	0.0035 (6)	0.0016 (6)	0.0036 (6)
C3"	0.0329 (9)	0.0280 (9)	0.0182 (7)	0.0042 (7)	0.0085 (7)	0.0009 (6)
C4"	0.0269 (9)	0.0268 (9)	0.0310 (9)	0.0068 (7)	0.0140 (7)	0.0036 (7)
C5"	0.0211 (8)	0.0325 (9)	0.0288 (8)	0.0069 (7)	0.0020 (6)	0.0082 (7)
C6"	0.0237 (8)	0.0275 (9)	0.0179 (7)	0.0037 (7)	0.0016 (6)	0.0032 (6)

Geometric parameters (Å, º)

Se—C1"	1.9244 (15)	C3'—C4'	1.396 (2)
Se—C3	1.9842 (15)	C3'—H3B	0.9500
O1—C2	1.4289 (18)	C4'—C5'	1.380 (2)
O1—C6	1.4405 (18)	C4'—H4B	0.9500
C2—C2'	1.5145 (19)	C5'—C6'	1.392 (2)
C2—C3	1.539 (2)	C5'—H5B	0.9500
C2—H2	1.0000	C6'—H6B	0.9500
C3—C4	1.529 (2)	C7'—H7A	0.9800
C3—H3	1.0000	C7'—H7B	0.9800
C4—C5	1.526 (2)	C7'—H7C	0.9800
C4—H4	0.9536	C1"—C2"	1.388 (2)
C4—H4A	0.9536	C1"—C6"	1.396 (2)
C5—C6	1.519 (2)	C2"—C3"	1.390 (2)
C5—H5	0.9754	C2"—H2C	0.9500
C5—H5A	0.9754	C3"—C4"	1.388 (3)
C6—H6	0.9844	C3"—H3C	0.9500
C6—H6A	0.9844	C4"—C5"	1.392 (2)
O2—C1'	1.3731 (18)	C4"—H4C	0.9500
O2—C7'	1.4284 (18)	C5"—C6"	1.382 (2)
C1'—C6'	1.390 (2)	C5"—H5C	0.9500
C1'—C2'	1.404 (2)	C6"—H6C	0.9500
C2'—C3'	1.390 (2)
C1"—Se—C3	99.14 (6)	C1'—C2'—C2	118.74 (13)
C2—O1—C6	110.71 (12)	C2'—C3'—C4'	120.61 (15)
O1—C2—C2'	108.62 (12)	C2'—C3'—H3B	119.7
O1—C2—C3	110.67 (11)	C4'—C3'—H3B	119.7
C2'—C2—C3	114.91 (12)	C5'—C4'—C3'	119.80 (15)
O1—C2—H2	107.4	C5'—C4'—H4B	120.1
C2'—C2—H2	107.4	C3'—C4'—H4B	120.1
C3—C2—H2	107.4	C4'—C5'—C6'	120.70 (14)
C4—C3—C2	109.31 (12)	C4'—C5'—H5B	119.6
C4—C3—Se	112.70 (10)	C6'—C5'—H5B	119.6
C2—C3—Se	108.13 (10)	C1'—C6'—C5'	119.37 (14)
C4—C3—H3	108.9	C1'—C6'—H6B	120.3
C2—C3—H3	108.9	C5'—C6'—H6B	120.3
Se—C3—H3	108.9	O2—C7'—H7A	109.5
C5—C4—C3	111.69 (13)	O2—C7'—H7B	109.5
C5—C4—H4	109.3	H7A—C7'—H7B	109.5
C3—C4—H4	109.3	O2—C7'—H7C	109.5
C5—C4—H4A	109.3	H7A—C7'—H7C	109.5
C3—C4—H4A	109.3	H7B—C7'—H7C	109.5
H4—C4—H4A	107.9	C2"—C1"—C6"	119.23 (14)
C6—C5—C4	110.60 (13)	C2"—C1"—Se	118.99 (12)
C6—C5—H5	109.5	C6"—C1"—Se	121.63 (11)
C4—C5—H5	109.5	C1"—C2"—C3"	120.40 (15)
C6—C5—H5A	109.5	C1"—C2"—H2C	119.8
C4—C5—H5A	109.5	C3"—C2"—H2C	119.8
H5—C5—H5A	108.1	C4"—C3"—C2"	120.18 (15)
O1—C6—C5	111.84 (13)	C4"—C3"—H3C	119.9
O1—C6—H6	109.2	C2"—C3"—H3C	119.9
C5—C6—H6	109.2	C3"—C4"—C5"	119.49 (15)
O1—C6—H6A	109.2	C3"—C4"—H4C	120.3
C5—C6—H6A	109.2	C5"—C4"—H4C	120.3
H6—C6—H6A	107.9	C6"—C5"—C4"	120.35 (15)
C1'—O2—C7'	117.40 (12)	C6"—C5"—H5C	119.8
O2—C1'—C6'	124.24 (14)	C4"—C5"—H5C	119.8
O2—C1'—C2'	115.11 (13)	C5"—C6"—C1"	120.32 (14)
C6'—C1'—C2'	120.65 (14)	C5"—C6"—H6C	119.8
C3'—C2'—C1'	118.86 (14)	C1"—C6"—H6C	119.8
C3'—C2'—C2	122.35 (13)
C6—O1—C2—C2'	169.53 (12)	C3—C2—C2'—C3'	−107.61 (16)
C6—O1—C2—C3	−63.46 (15)	O1—C2—C2'—C1'	−160.62 (12)
O1—C2—C3—C4	57.78 (15)	C3—C2—C2'—C1'	74.84 (17)
C2'—C2—C3—C4	−178.76 (12)	C1'—C2'—C3'—C4'	0.1 (2)
O1—C2—C3—Se	−65.24 (13)	C2—C2'—C3'—C4'	−177.41 (14)
C2'—C2—C3—Se	58.22 (14)	C2'—C3'—C4'—C5'	−0.4 (2)
C1"—Se—C3—C4	56.72 (11)	C3'—C4'—C5'—C6'	0.2 (2)
C1"—Se—C3—C2	177.66 (10)	O2—C1'—C6'—C5'	179.88 (14)
C2—C3—C4—C5	−50.98 (16)	C2'—C1'—C6'—C5'	−0.6 (2)
Se—C3—C4—C5	69.28 (14)	C4'—C5'—C6'—C1'	0.3 (2)
C3—C4—C5—C6	49.53 (18)	C3—Se—C1"—C2"	−119.70 (13)
C2—O1—C6—C5	61.79 (17)	C3—Se—C1"—C6"	64.77 (14)
C4—C5—C6—O1	−54.16 (19)	C6"—C1"—C2"—C3"	1.5 (2)
C7'—O2—C1'—C6'	−5.4 (2)	Se—C1"—C2"—C3"	−174.13 (13)
C7'—O2—C1'—C2'	174.98 (13)	C1"—C2"—C3"—C4"	−1.5 (3)
O2—C1'—C2'—C3'	179.95 (13)	C2"—C3"—C4"—C5"	0.0 (3)
C6'—C1'—C2'—C3'	0.4 (2)	C3"—C4"—C5"—C6"	1.4 (3)
O2—C1'—C2'—C2	−2.41 (19)	C4"—C5"—C6"—C1"	−1.3 (3)
C6'—C1'—C2'—C2	177.99 (14)	C2"—C1"—C6"—C5"	−0.1 (2)
O1—C2—C2'—C3'	16.94 (19)	Se—C1"—C6"—C5"	175.40 (13)