organic compounds
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.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802013272/tk6071sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802013272/tk6071Isup2.hkl |
CCDC reference: 193780
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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.
cis-2-(2-Methoxyphenyl)-3-(phenylselenyl)tetrahydropyran top
Crystal data top
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) Å3 | 0.36 × 0.28 × 0.14 mm |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.019 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.052 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0303P)2 + 0.2068P] where P = (Fo2 + 2Fc2)/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 (Å2) top
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 (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
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) top
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) |