Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100015717/qa0448sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100015717/qa0448Isup2.hkl |
CCDC reference: 156219
The preparation of the title compound was presented in a report by Yamazaki et al. (1999). Single crystals were grown by slow evaporation from a mixture of hexane and ethyl acetate.
No Friedel pairs were measured. All H atoms were located in difference maps. Only their Uiso were refined, but some of these were fixed.
Data collection: MSC/AFC Diffractometer Control (Rigaku, 1991); cell refinement: MSC/AFC Diffractometer Control; data reduction: TEXSAN (Molecular Structure Corporation, 1998); program(s) used to solve structure: MULTAN88 (Debaedemaeker et al., 1985); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEP-II (Johnson, 1976); software used to prepare material for publication: TEXSAN.
C21H20F3NO4 | Dx = 1.329 Mg m−3 |
Mr = 407.39 | Mo Kα radiation, λ = 0.7107 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 13.115 (3) Å | θ = 14.6–17.2° |
b = 24.305 (3) Å | µ = 0.11 mm−1 |
c = 6.388 (3) Å | T = 298 K |
V = 2036.2 (11) Å3 | Plate, colourless |
Z = 4 | 0.70 × 0.50 × 0.30 mm |
Rigaku AFC-5R diffractometer | Rint = 0.017 |
ω–2θ scans | θmax = 27.5° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→17 |
Tmin = 0.865, Tmax = 0.999 | k = 0→31 |
2716 measured reflections | l = 0→8 |
2641 independent reflections | 4 standard reflections every 150 reflections |
1619 reflections with F2 > 2σ(F2) | intensity decay: 0.3% |
Refinement on F2 | w = 1/[σ2(Fo2) + 0.00160(Fo2)2] |
R[F2 > 2σ(F2)] = 0.048 | (Δ/σ)max = 0.0002 |
wR(F2) = 0.137 | Δρmax = 0.15 e Å−3 |
S = 2.00 | Δρmin = −0.12 e Å−3 |
2689 reflections | Extinction correction: Zachariasen (1967), type 2, Gaussian isotropic |
275 parameters | Extinction coefficient: 0.007 (2) |
Only H-atom displacement parameters refined | Absolute structure: From the configuration of C14 in the starting material. |
C21H20F3NO4 | V = 2036.2 (11) Å3 |
Mr = 407.39 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 13.115 (3) Å | µ = 0.11 mm−1 |
b = 24.305 (3) Å | T = 298 K |
c = 6.388 (3) Å | 0.70 × 0.50 × 0.30 mm |
Rigaku AFC-5R diffractometer | 1619 reflections with F2 > 2σ(F2) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.017 |
Tmin = 0.865, Tmax = 0.999 | 4 standard reflections every 150 reflections |
2716 measured reflections | intensity decay: 0.3% |
2641 independent reflections |
R[F2 > 2σ(F2)] = 0.048 | Only H-atom displacement parameters refined |
wR(F2) = 0.137 | Δρmax = 0.15 e Å−3 |
S = 2.00 | Δρmin = −0.12 e Å−3 |
2689 reflections | Absolute structure: From the configuration of C14 in the starting material. |
275 parameters |
Refinement. Refinement using reflections with F2 > −10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) is based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
F1 | 0.5820 (2) | 0.4382 (1) | −0.0826 (5) | 0.119 (1) | |
F2 | 0.5398 (3) | 0.50701 (10) | 0.1035 (7) | 0.141 (1) | |
F3 | 0.6764 (2) | 0.4617 (1) | 0.1701 (7) | 0.147 (1) | |
O1 | 0.0955 (2) | 0.4271 (1) | 0.1082 (6) | 0.0943 (10) | |
O2 | 0.5027 (2) | 0.3542 (1) | 0.6123 (4) | 0.0917 (9) | |
O3 | 0.6361 (2) | 0.2553 (1) | 0.1562 (4) | 0.0825 (8) | |
O4 | 0.6372 (2) | 0.1957 (1) | 0.4195 (4) | 0.0888 (9) | |
N1 | 0.5662 (2) | 0.2763 (1) | 0.4795 (4) | 0.0610 (7) | |
C1 | 0.0548 (4) | 0.4043 (3) | −0.074 (1) | 0.124 (2) | |
C2 | 0.1990 (3) | 0.4238 (1) | 0.1358 (7) | 0.074 (1) | |
C3 | 0.2383 (3) | 0.4471 (1) | 0.3165 (7) | 0.079 (1) | |
C4 | 0.3408 (3) | 0.4452 (1) | 0.3562 (6) | 0.075 (1) | |
C5 | 0.4075 (3) | 0.4204 (1) | 0.2182 (6) | 0.0666 (10) | |
C6 | 0.3677 (3) | 0.3978 (1) | 0.0384 (6) | 0.078 (1) | |
C7 | 0.2644 (3) | 0.3988 (2) | −0.0035 (7) | 0.081 (1) | |
C8 | 0.5214 (3) | 0.4199 (1) | 0.2639 (6) | 0.077 (1) | |
C9 | 0.5790 (4) | 0.4561 (2) | 0.111 (1) | 0.101 (2) | |
C10 | 0.5673 (3) | 0.3619 (2) | 0.2640 (6) | 0.071 (1) | |
C11 | 0.5418 (2) | 0.3321 (1) | 0.4623 (5) | 0.0639 (9) | |
C12 | 0.6155 (3) | 0.2442 (2) | 0.3326 (6) | 0.0659 (10) | |
C13 | 0.6071 (3) | 0.1939 (2) | 0.6363 (6) | 0.087 (1) | |
C14 | 0.5476 (3) | 0.2469 (2) | 0.6752 (5) | 0.078 (1) | |
C15 | 0.4339 (3) | 0.2365 (2) | 0.7193 (6) | 0.085 (1) | |
C16 | 0.3780 (2) | 0.2053 (2) | 0.5523 (6) | 0.073 (1) | |
C17 | 0.3464 (2) | 0.2324 (2) | 0.3743 (7) | 0.088 (1) | |
C18 | 0.2966 (3) | 0.2048 (4) | 0.2160 (7) | 0.129 (2) | |
C19 | 0.2783 (4) | 0.1495 (5) | 0.236 (1) | 0.149 (3) | |
C20 | 0.3096 (4) | 0.1211 (3) | 0.409 (2) | 0.137 (3) | |
C21 | 0.3587 (3) | 0.1494 (2) | 0.571 (1) | 0.111 (2) | |
H1a | 0.0569 | 0.3623 | −0.1217 | 0.1469* | |
H1b | 0.0020 | 0.4167 | −0.0983 | 0.1469* | |
H1c | 0.0966 | 0.4213 | −0.1815 | 0.1469* | |
H3 | 0.1965 | 0.4657 | 0.4357 | 0.11 (1)* | |
H4 | 0.3792 | 0.4607 | 0.4941 | 0.13 (1)* | |
H6 | 0.4156 | 0.3829 | −0.0596 | 0.11 (1)* | |
H7 | 0.2384 | 0.3826 | −0.1284 | 0.11 (1)* | |
H8 | 0.5227 | 0.4356 | 0.4050 | 0.065 (9)* | |
H10a | 0.5656 | 0.3452 | 0.1470 | 0.064 (9)* | |
H10b | 0.6481 | 0.3634 | 0.2505 | 0.08 (1)* | |
H13a | 0.6670 | 0.1942 | 0.6961 | 0.09 (1)* | |
H13b | 0.5517 | 0.1542 | 0.6558 | 0.10 (1)* | |
H14 | 0.5771 | 0.2597 | 0.8009 | 0.10 (1)* | |
H15a | 0.4291 | 0.2166 | 0.8459 | 0.11 (1)* | |
H15b | 0.4020 | 0.2715 | 0.7349 | 0.11 (1)* | |
H17 | 0.3580 | 0.2713 | 0.3611 | 0.1051* | |
H18 | 0.2747 | 0.2222 | 0.0916 | 0.1629* | |
H19 | 0.2436 | 0.1276 | 0.1333 | 0.1900* | |
H20 | 0.2991 | 0.0814 | 0.4275 | 0.1637* | |
H21 | 0.3816 | 0.1300 | 0.6976 | 0.1350* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.142 (2) | 0.093 (2) | 0.122 (2) | −0.008 (2) | 0.053 (2) | 0.004 (2) |
F2 | 0.156 (2) | 0.061 (1) | 0.206 (3) | −0.005 (1) | 0.059 (2) | 0.000 (2) |
F3 | 0.106 (2) | 0.124 (2) | 0.210 (4) | −0.042 (2) | 0.027 (2) | 0.001 (3) |
O1 | 0.084 (2) | 0.085 (2) | 0.115 (2) | 0.005 (1) | 0.001 (2) | 0.013 (2) |
O2 | 0.108 (2) | 0.102 (2) | 0.065 (2) | 0.005 (2) | 0.021 (2) | −0.024 (1) |
O3 | 0.110 (2) | 0.087 (2) | 0.050 (1) | 0.022 (1) | 0.013 (1) | −0.001 (1) |
O4 | 0.102 (2) | 0.091 (2) | 0.074 (2) | 0.027 (1) | 0.004 (1) | 0.018 (1) |
N1 | 0.059 (1) | 0.082 (2) | 0.042 (1) | 0.005 (1) | −0.001 (1) | −0.003 (1) |
C1 | 0.115 (4) | 0.129 (4) | 0.128 (5) | −0.008 (3) | −0.022 (4) | 0.018 (4) |
C2 | 0.084 (2) | 0.052 (2) | 0.087 (3) | 0.004 (2) | 0.012 (2) | 0.012 (2) |
C3 | 0.092 (3) | 0.064 (2) | 0.082 (3) | 0.008 (2) | 0.022 (2) | −0.010 (2) |
C4 | 0.084 (2) | 0.063 (2) | 0.078 (2) | 0.001 (2) | 0.018 (2) | −0.016 (2) |
C5 | 0.080 (2) | 0.047 (2) | 0.073 (2) | −0.002 (1) | 0.017 (2) | −0.007 (2) |
C6 | 0.096 (3) | 0.068 (2) | 0.071 (2) | 0.006 (2) | 0.021 (2) | −0.011 (2) |
C7 | 0.095 (3) | 0.074 (2) | 0.073 (2) | 0.002 (2) | 0.009 (2) | −0.002 (2) |
C8 | 0.085 (2) | 0.066 (2) | 0.081 (2) | −0.008 (2) | 0.020 (2) | −0.022 (2) |
C9 | 0.099 (3) | 0.063 (2) | 0.143 (5) | −0.012 (2) | 0.022 (3) | −0.010 (3) |
C10 | 0.075 (2) | 0.076 (2) | 0.063 (2) | −0.001 (2) | 0.012 (2) | −0.014 (2) |
C11 | 0.058 (2) | 0.080 (2) | 0.054 (2) | −0.004 (2) | 0.005 (2) | −0.016 (2) |
C12 | 0.072 (2) | 0.076 (2) | 0.050 (2) | 0.011 (2) | −0.005 (2) | −0.002 (2) |
C13 | 0.069 (2) | 0.124 (3) | 0.068 (2) | 0.007 (2) | −0.008 (2) | 0.030 (2) |
C14 | 0.072 (2) | 0.117 (3) | 0.043 (2) | 0.001 (2) | −0.004 (2) | 0.009 (2) |
C15 | 0.079 (2) | 0.123 (3) | 0.053 (2) | −0.006 (2) | 0.012 (2) | 0.007 (2) |
C16 | 0.055 (2) | 0.102 (3) | 0.062 (2) | 0.008 (2) | 0.010 (2) | 0.003 (2) |
C17 | 0.046 (2) | 0.139 (4) | 0.079 (3) | 0.003 (2) | 0.003 (2) | 0.008 (3) |
C18 | 0.049 (2) | 0.266 (9) | 0.072 (3) | −0.002 (3) | 0.000 (2) | −0.012 (4) |
C19 | 0.062 (3) | 0.230 (9) | 0.154 (7) | −0.008 (4) | 0.008 (4) | −0.090 (7) |
C20 | 0.076 (3) | 0.127 (5) | 0.207 (8) | −0.008 (3) | 0.011 (4) | −0.052 (5) |
C21 | 0.073 (2) | 0.107 (4) | 0.151 (5) | 0.000 (2) | 0.007 (3) | 0.009 (4) |
F1—C9 | 1.310 (6) | C8—C9 | 1.518 (6) |
F2—C9 | 1.340 (5) | C8—C10 | 1.531 (5) |
F3—C9 | 1.339 (6) | C8—H8 | 0.98) |
O1—C1 | 1.392 (7) | C10—C11 | 1.498 (5) |
O1—C2 | 1.372 (5) | C10—H10a | 0.85 |
O2—C11 | 1.213 (4) | C10—H10b | 1.06 |
O3—C12 | 1.190 (4) | C13—C14 | 1.526 (6) |
O4—C12 | 1.334 (4) | C13—H13a | 0.87 |
O4—C13 | 1.441 (5) | C13—H13b | 1.21 |
N1—C11 | 1.397 (4) | C14—C15 | 1.539 (5) |
N1—C12 | 1.380 (4) | C14—H14 | 0.94 |
N1—C14 | 1.460 (4) | C15—C16 | 1.499 (6) |
C1—H1a | 1.07 | C15—H15a | 0.94 |
C1—H1b | 0.77 | C15—H15b | 0.95 |
C1—H1c | 0.97 | C16—C17 | 1.378 (6) |
C2—C3 | 1.384 (6) | C16—C21 | 1.388 (6) |
C2—C7 | 1.377 (6) | C17—C18 | 1.378 (8) |
C3—C4 | 1.368 (5) | C17—H17 | 0.96 |
C3—H3 | 1.04 | C18—C19 | 1.37 (1) |
C4—C5 | 1.380 (5) | C18—H18 | 0.94 |
C4—H4 | 1.08 | C19—C20 | 1.36 (1) |
C5—C6 | 1.377 (5) | C19—H19 | 0.96) |
C5—C8 | 1.523 (5) | C20—C21 | 1.403 (9) |
C6—C7 | 1.382 (6) | C20—H20 | 0.98 |
C6—H6 | 0.96 | C21—H21 | 0.98 |
C7—H7 | 0.95 | ||
F1···O2i | 3.008 (4) | O3···C14i | 3.290 (4) |
F1···C19ii | 3.483 (8) | O3···C18ii | 3.321 (6) |
F2···C1iii | 3.231 (7) | O4···C1ii | 3.459 (8) |
F2···C20iv | 3.406 (7) | O4···C17viii | 3.509 (5) |
O1···C13v | 3.367 (5) | C2···C13v | 3.429 (6) |
O1···C4vi | 3.595 (5) | C14···C18viii | 3.539 (6) |
O2···C6vii | 3.415 (4) | ||
C1—O1—C2 | 117.6 (4) | C11—C10—H10b | 107.9 (3) |
C12—O4—C13 | 111.6 (3) | H10a—C10—H10b | 88.4 (3) |
C11—N1—C12 | 127.0 (3) | O2—C11—N1 | 117.7 (3) |
C11—N1—C14 | 120.3 (3) | O2—C11—C10 | 123.2 (3) |
C12—N1—C14 | 112.6 (3) | N1—C11—C10 | 119.0 (3) |
O1—C1—H1a | 127.6 (5) | O3—C12—O4 | 123.0 (3) |
O1—C1—H1b | 111.1 (7) | O3—C12—N1 | 128.6 (3) |
O1—C1—H1c | 101.9 (5) | O4—C12—N1 | 108.4 (3) |
H1a—C1—H1b | 109.7 (6) | O4—C13—C14 | 105.7 (3) |
H1a—C1—H1c | 100.8 (6) | O4—C13—H13a | 100.0 (4) |
H1b—C1—H1c | 101.3 (6) | O4—C13—H13b | 106.7 (4) |
O1—C2—C3 | 116.8 (4) | C14—C13—H13a | 112.4 (5) |
O1—C2—C7 | 124.0 (4) | C14—C13—H13b | 110.3 (3) |
C3—C2—C7 | 119.2 (4) | H13a—C13—H13b | 120.0 (4) |
C2—C3—C4 | 120.4 (3) | N1—C14—C13 | 100.8 (3) |
C2—C3—H3 | 126.2 (4) | N1—C14—C15 | 113.5 (3) |
C4—C3—H3 | 113.3 (4) | N1—C14—H14 | 119.8 (4) |
C3—C4—C5 | 121.2 (4) | C13—C14—C15 | 112.7 (4) |
C3—C4—H4 | 126.7 (4) | C13—C14—H14 | 102.0 (3) |
C5—C4—H4 | 112.1 (3) | C15—C14—H14 | 107.2 (3) |
C4—C5—C6 | 117.9 (3) | C14—C15—C16 | 115.3 (3) |
C4—C5—C8 | 120.2 (3) | C14—C15—H15a | 107.8 (3) |
C6—C5—C8 | 121.9 (3) | C14—C15—H15b | 107.3 (4) |
C5—C6—C7 | 121.7 (3) | C16—C15—H15a | 108.6 (4) |
C5—C6—H6 | 116.6 (4) | C16—C15—H15b | 108.0 (3) |
C7—C6—H6 | 121.6 (4) | H15a—C15—H15b | 109.7 (4) |
C2—C7—C6 | 119.6 (4) | C15—C16—C17 | 119.6 (4) |
C2—C7—H7 | 120.1 (4) | C15—C16—C21 | 121.4 (4) |
C6—C7—H7 | 120.3 (4) | C17—C16—C21 | 119.0 (4) |
C5—C8—C9 | 111.1 (4) | C16—C17—C18 | 121.0 (5) |
C5—C8—C10 | 113.2 (3) | C16—C17—H17 | 119.6 (4) |
C5—C8—H8 | 100.9 (3) | C18—C17—H17 | 119.4 (5) |
C9—C8—C10 | 109.8 (3) | C17—C18—C19 | 119.5 (6) |
C9—C8—H8 | 111.0 (4) | C17—C18—H18 | 122.8 (9) |
C10—C8—H8 | 110.6 (4) | C19—C18—H18 | 117.7 (8) |
F1—C9—F2 | 106.6 (5) | C18—C19—C20 | 121.2 (6) |
F1—C9—F3 | 105.8 (5) | C18—C19—H19 | 124 (1) |
F1—C9—C8 | 115.5 (4) | C20—C19—H19 | 114 (1) |
F2—C9—F3 | 106.4 (4) | C19—C20—C21 | 119.3 (6) |
F2—C9—C8 | 111.5 (4) | C19—C20—H20 | 123.7 (9) |
F3—C9—C8 | 110.5 (5) | C21—C20—H20 | 117.1 (9) |
C8—C10—C11 | 111.0 (3) | C16—C21—C20 | 119.9 (6) |
C8—C10—H10a | 115.4 (4) | C16—C21—H21 | 119.1 (6) |
C8—C10—H10b | 111.1 (3) | C20—C21—H21 | 120.9 (6) |
C11—C10—H10a | 120.3 (4) | ||
F1—C9—C8—C5 | −69.0 (5) | C4—C3—C2—C7 | 0.0 (5) |
F1—C9—C8—C10 | 57.0 (6) | C4—C5—C6—C7 | −0.9 (5) |
F2—C9—C8—C5 | 52.9 (5) | C4—C5—C8—C9 | −111.3 (4) |
F2—C9—C8—C10 | 178.9 (4) | C4—C5—C8—C10 | 124.7 (4) |
F3—C9—C8—C5 | 171.0 (4) | C5—C8—C10—C11 | −76.9 (4) |
F3—C9—C8—C10 | −63.0 (5) | C6—C5—C8—C9 | 67.2 (4) |
O1—C2—C3—C4 | 179.6 (3) | C6—C5—C8—C10 | −56.8 (5) |
O1—C2—C7—C6 | 179.8 (4) | C7—C6—C5—C8 | −179.4 (4) |
O2—C11—N1—C12 | −176.4 (3) | C9—C8—C10—C11 | 158.3 (3) |
O2—C11—N1—C14 | −1.9 (4) | C10—C11—N1—C12 | 2.0 (5) |
O2—C11—C10—C8 | −9.7 (5) | C10—C11—N1—C14 | 176.5 (3) |
O3—C12—O4—C13 | 178.0 (4) | C11—N1—C14—C13 | −167.5 (3) |
O3—C12—N1—C11 | −9.6 (6) | C11—N1—C14—C15 | 71.7 (4) |
O3—C12—N1—C14 | 175.5 (4) | C12—O4—C13—C14 | 7.6 (4) |
O4—C12—N1—C11 | 171.2 (3) | C12—N1—C14—C13 | 7.8 (4) |
O4—C12—N1—C14 | −3.6 (4) | C12—N1—C14—C15 | −113.1 (4) |
O4—C13—C14—N1 | −8.8 (4) | C13—C14—C15—C16 | −56.8 (5) |
O4—C13—C14—C15 | 112.6 (3) | C14—C15—C16—C17 | −79.1 (5) |
N1—C11—C10—C8 | 172.0 (3) | C14—C15—C16—C21 | 99.8 (4) |
N1—C12—O4—C13 | −2.8 (4) | C15—C16—C17—C18 | 178.7 (3) |
N1—C14—C15—C16 | 57.0 (5) | C15—C16—C21—C20 | −177.6 (4) |
C1—O1—C2—C3 | 179.5 (4) | C16—C17—C18—C19 | 0.0 (6) |
C1—O1—C2—C7 | −0.9 (5) | C16—C21—C20—C19 | −2.1 (8) |
C2—C3—C4—C5 | 0.1 (6) | C17—C16—C21—C20 | 1.3 (6) |
C2—C7—C6—C5 | 1.0 (6) | C17—C18—C19—C20 | −0.8 (8) |
C3—C2—C7—C6 | −0.5 (5) | C18—C17—C16—C21 | −0.3 (5) |
C3—C4—C5—C6 | 0.3 (5) | C18—C19—C20—C21 | 1.9 (9) |
C3—C4—C5—C8 | 178.9 (3) |
Symmetry codes: (i) x, y, z−1; (ii) x+1/2, −y+1/2, −z; (iii) −x+1/2, −y+1, z+1/2; (iv) −x+1, y+1/2, −z+1/2; (v) x−1/2, −y+1/2, −z+1; (vi) −x+1/2, −y+1, z−1/2; (vii) x, y, z+1; (viii) x+1/2, −y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C21H20F3NO4 |
Mr | 407.39 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 298 |
a, b, c (Å) | 13.115 (3), 24.305 (3), 6.388 (3) |
V (Å3) | 2036.2 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.70 × 0.50 × 0.30 |
Data collection | |
Diffractometer | Rigaku AFC-5R diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.865, 0.999 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 2716, 2641, 1619 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.137, 2.00 |
No. of reflections | 2689 |
No. of parameters | 275 |
No. of restraints | ? |
H-atom treatment | Only H-atom displacement parameters refined |
Δρmax, Δρmin (e Å−3) | 0.15, −0.12 |
Absolute structure | From the configuration of C14 in the starting material. |
Computer programs: MSC/AFC Diffractometer Control (Rigaku, 1991), MSC/AFC Diffractometer Control, TEXSAN (Molecular Structure Corporation, 1998), MULTAN88 (Debaedemaeker et al., 1985), TEXSAN, ORTEP-II (Johnson, 1976).
F1—C9 | 1.310 (6) | C5—C6 | 1.377 (5) |
F2—C9 | 1.340 (5) | C5—C8 | 1.523 (5) |
F3—C9 | 1.339 (6) | C6—C7 | 1.382 (6) |
O1—C1 | 1.392 (7) | C8—C9 | 1.518 (6) |
O1—C2 | 1.372 (5) | C8—C10 | 1.531 (5) |
O2—C11 | 1.213 (4) | C10—C11 | 1.498 (5) |
O3—C12 | 1.190 (4) | C13—C14 | 1.526 (6) |
O4—C12 | 1.334 (4) | C14—C15 | 1.539 (5) |
O4—C13 | 1.441 (5) | C15—C16 | 1.499 (6) |
N1—C11 | 1.397 (4) | C16—C17 | 1.378 (6) |
N1—C12 | 1.380 (4) | C16—C21 | 1.388 (6) |
N1—C14 | 1.460 (4) | C17—C18 | 1.378 (8) |
C2—C3 | 1.384 (6) | C18—C19 | 1.37 (1) |
C2—C7 | 1.377 (6) | C19—C20 | 1.36 (1) |
C3—C4 | 1.368 (5) | C20—C21 | 1.403 (9) |
C4—C5 | 1.380 (5) | ||
C1—O1—C2 | 117.6 (4) | F2—C9—C8 | 111.5 (4) |
C12—O4—C13 | 111.6 (3) | F3—C9—C8 | 110.5 (5) |
C11—N1—C12 | 127.0 (3) | C8—C10—C11 | 111.0 (3) |
C11—N1—C14 | 120.3 (3) | O2—C11—N1 | 117.7 (3) |
C12—N1—C14 | 112.6 (3) | O2—C11—C10 | 123.2 (3) |
O1—C2—C3 | 116.8 (4) | N1—C11—C10 | 119.0 (3) |
O1—C2—C7 | 124.0 (4) | O3—C12—O4 | 123.0 (3) |
C3—C2—C7 | 119.2 (4) | O3—C12—N1 | 128.6 (3) |
C2—C3—C4 | 120.4 (3) | O4—C12—N1 | 108.4 (3) |
C3—C4—C5 | 121.2 (4) | O4—C13—C14 | 105.7 (3) |
C4—C5—C6 | 117.9 (3) | N1—C14—C13 | 100.8 (3) |
C4—C5—C8 | 120.2 (3) | N1—C14—C15 | 113.5 (3) |
C6—C5—C8 | 121.9 (3) | C13—C14—C15 | 112.7 (4) |
C5—C6—C7 | 121.7 (3) | C14—C15—C16 | 115.3 (3) |
C2—C7—C6 | 119.6 (4) | C15—C16—C17 | 119.6 (4) |
C5—C8—C9 | 111.1 (4) | C15—C16—C21 | 121.4 (4) |
C5—C8—C10 | 113.2 (3) | C17—C16—C21 | 119.0 (4) |
C9—C8—C10 | 109.8 (3) | C16—C17—C18 | 121.0 (5) |
F1—C9—F2 | 106.6 (5) | C17—C18—C19 | 119.5 (6) |
F1—C9—F3 | 105.8 (5) | C18—C19—C20 | 121.2 (6) |
F1—C9—C8 | 115.5 (4) | C19—C20—C21 | 119.3 (6) |
F2—C9—F3 | 106.4 (4) | C16—C21—C20 | 119.9 (6) |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register
The title compound, (I), was prepared by way of Michael addition of an organocopper species to 3-[(E)-4,4,4-trifluorobut-2-enoyl]oxazolidin-2-ones in order to obtain optically active molecules with a CF3 moiety at the chiral centre. The structure determination was made so as to clarify how the molecule is built up through the synthetic reaction. The C atom at the chiral centre takes R configuration. From this establishment, a useful information on the intermediate process of the reaction was deduced: the construction of the molecule possibly proceeded via intramolecular bidentate chelation between Cu atom and carbonyl groups, rather than a conformation which without such chelation reduces the dipolar repulsion between the carbonyl groups and results in S configuration of the chiral atom owing to stereoselectivity (Yamazaki et al., 1999). The configuration of the asymmetric carbon atom in the five-membered ring is S. The C—F bond lengths are 1.330 (6) Å on average. The CF3 and CH3 groups as well as the benzene-ring part show large atomic displacement parameters. \scheme