Conformational disorder and inversions of the lactone ring induce structural transformations in the crystals of 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin, C14H18O3. The onset of ordering of the lactone ring at 300 K proceeds continuously, changes the space group from P21/m to P21/c and doubles the unit cell; the abrupt inversion of the lactone rings at 225 K changes the crystal translational symmetry in the (010) plane. The mechanism combining the molecular conformation and dynamics with the crystal structure, its symmetry, and phase transitions is presented.
Supporting information
| Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768101017955/bm0046sup1.cif Contains datablocks a308, a319, a329, cum110c, cum150c, cum220, cum222, cum224, cum225c, cum230, cum250, cum278, cum285, cum293 |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101017955/bm0046a308sup2.hkl Contains datablock a308 |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101017955/bm0046a319sup3.hkl Contains datablock a319 |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101017955/bm0046a329sup4.hkl Contains datablock a329 |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101017955/bm0046cum110csup5.hkl Contains datablock cum110c |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101017955/bm0046cum150csup6.hkl Contains datablock cum150c |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101017955/bm0046cum220sup7.hkl Contains datablock cum220 |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101017955/bm0046cum222sup8.hkl Contains datablock cum222 |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101017955/bm0046cum224sup9.hkl Contains datablock cum224 |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101017955/bm0046cum225csup10.hkl Supplementary material |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101017955/bm0046cum230sup11.hkl Supplementary material |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101017955/bm0046cum250sup12.hkl Supplementary material |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101017955/bm0046cum278sup13.hkl Supplementary material |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101017955/bm0046cum285sup14.hkl Supplementary material |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101017955/bm0046cum293sup15.hkl Supplementary material |
CCDC references: 180202; 180203; 180204; 180205; 180206; 180207; 180208; 180209; 180210; 180211; 180212; 180213; 180214; 180215
For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
(a308) 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin
top
Crystal data top
C14H18O3 | V = 645.3 (2) Å3 |
Mr = 234.28 | Z = 2 |
P21/m, monoclinic | F(000) = 252 |
a = 9.753 (2) Å | Dx = 1.206 Mg m−3 |
b = 6.933 (1) Å | Cu Kα radiation, λ = 1.54178 Å |
c = 9.572 (2) Å | µ = 0.68 mm−1 |
α = 90° | T = 306 K |
β = 94.39 (3)° | , colourlees |
γ = 90° | 0.35 × 0.25 × 0.12 mm |
Data collection top
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 60.1°, θmin = 4.6° |
1106 measured reflections | h = −10→10 |
1045 independent reflections | k = −7→0 |
864 reflections with I > 2σ(I) | l = 0→10 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.033P)2 + 0.555P] where P = (Fo2 + 2Fc2)/3 |
S = 0.93 | (Δ/σ)max = 1.111 |
1045 reflections | Δρmax = 0.16 e Å−3 |
157 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.048 (2) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.10337 (19) | 0.2500 | 0.4954 (2) | 0.0704 (8) | |
O2 | −0.1147 (2) | 0.2500 | 0.5232 (3) | 0.1068 (12) | |
O6 | 0.6497 (2) | 0.2500 | 0.6764 (3) | 0.0645 (7) | |
H6 | 0.703 (5) | 0.2500 | 0.607 (5) | 0.122 (19)* | |
C2 | −0.0006 (3) | 0.2500 | 0.5743 (4) | 0.0713 (11) | |
C3 | 0.0381 (5) | 0.3542 (10) | 0.7114 (5) | 0.0729 (16) | 0.50 |
H3A | −0.046 (5) | 0.336 (7) | 0.759 (5) | 0.083 (16)* | 0.50 |
H3B | 0.073 (5) | 0.513 (7) | 0.696 (6) | 0.064 (16)* | 0.50 |
C4 | 0.1627 (3) | 0.2500 | 0.7908 (4) | 0.0685 (11) | |
C41 | 0.1953 (9) | 0.3885 (18) | 0.9212 (7) | 0.121 (4) | 0.50 |
H41A | 0.2178 | 0.5175 | 0.8869 | 0.08 (9)* | 0.25 |
H41B | 0.2735 | 0.3426 | 0.9783 | 0.04 (2)* | 0.25 |
H41C | 0.1178 | 0.3998 | 0.9751 | 0.08 (3)* | 0.25 |
H41D | 0.1882 | 0.3224 | 1.0066 | 0.17 (7)* | 0.25 |
H41E | 0.1326 | 0.4974 | 0.9153 | 0.21 (16)* | 0.25 |
H41F | 0.2883 | 0.4402 | 0.9184 | 0.38 (19)* | 0.25 |
C42 | 0.1284 (8) | 0.0503 (16) | 0.8300 (13) | 0.117 (3) | 0.50 |
H42A | 0.0555 | 0.0555 | 0.8933 | 0.05 (2)* | 0.25 |
H42B | 0.2077 | −0.0082 | 0.8775 | 0.05 (8)* | 0.25 |
H42C | 0.0986 | −0.0203 | 0.7488 | 0.20 (18)* | 0.25 |
H42D | 0.1858 | −0.0375 | 0.7864 | 2.0 (18)* | 0.25 |
H42E | 0.0335 | 0.0262 | 0.8022 | 0.13 (5)* | 0.25 |
H42F | 0.1426 | 0.0383 | 0.9310 | 0.15 (13)* | 0.25 |
C5 | 0.4203 (3) | 0.2500 | 0.7319 (3) | 0.0467 (8) | |
C51 | 0.4810 (5) | 0.2500 | 0.8820 (5) | 0.0834 (14) | |
H51A | 0.582 (8) | 0.2500 | 0.878 (7) | 0.22 (3)* | |
H51C | 0.458 (4) | 0.149 (6) | 0.932 (4) | 0.163 (18)* | |
C6 | 0.5129 (3) | 0.2500 | 0.6283 (3) | 0.0448 (8) | |
C7 | 0.4731 (3) | 0.2500 | 0.4859 (3) | 0.0430 (7) | |
C71 | 0.5798 (4) | 0.2500 | 0.3803 (4) | 0.0584 (10) | |
H71A | 0.544 (4) | 0.2500 | 0.286 (5) | 0.102 (15)* | |
H71B | 0.642 (3) | 0.141 (4) | 0.392 (3) | 0.104 (10)* | |
C8 | 0.3331 (3) | 0.2500 | 0.4446 (3) | 0.0428 (7) | |
C81 | 0.2809 (4) | 0.2500 | 0.2929 (4) | 0.0597 (10) | |
H81A | 0.192 (5) | 0.2500 | 0.278 (5) | 0.13 (2)* | |
H81C | 0.306 (3) | 0.139 (5) | 0.238 (3) | 0.125 (12)* | |
C9 | 0.2418 (3) | 0.2500 | 0.5493 (3) | 0.0435 (7) | |
C10 | 0.2789 (3) | 0.2500 | 0.6912 (3) | 0.0460 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0318 (11) | 0.117 (2) | 0.0628 (14) | 0.000 | 0.0041 (10) | 0.000 |
O2 | 0.0318 (14) | 0.165 (3) | 0.124 (3) | 0.000 | 0.0091 (14) | 0.000 |
O6 | 0.0358 (12) | 0.0768 (17) | 0.0793 (17) | 0.000 | −0.0063 (11) | 0.000 |
C2 | 0.0360 (18) | 0.100 (3) | 0.079 (2) | 0.000 | 0.0127 (17) | 0.000 |
C3 | 0.048 (3) | 0.104 (5) | 0.070 (3) | 0.019 (3) | 0.025 (2) | 0.003 (3) |
C4 | 0.055 (2) | 0.100 (3) | 0.053 (2) | 0.000 | 0.0196 (16) | 0.000 |
C41 | 0.095 (5) | 0.213 (11) | 0.057 (4) | 0.059 (6) | 0.015 (4) | −0.030 (6) |
C42 | 0.082 (5) | 0.148 (8) | 0.128 (7) | 0.016 (5) | 0.048 (5) | 0.081 (8) |
C5 | 0.0455 (16) | 0.0479 (18) | 0.0461 (17) | 0.000 | 0.0005 (13) | 0.000 |
C51 | 0.073 (3) | 0.122 (4) | 0.053 (2) | 0.000 | −0.0072 (19) | 0.000 |
C6 | 0.0334 (15) | 0.0403 (17) | 0.0599 (18) | 0.000 | −0.0016 (12) | 0.000 |
C7 | 0.0376 (16) | 0.0371 (16) | 0.0555 (18) | 0.000 | 0.0105 (13) | 0.000 |
C71 | 0.0453 (19) | 0.063 (2) | 0.070 (3) | 0.000 | 0.0218 (17) | 0.000 |
C8 | 0.0399 (15) | 0.0424 (17) | 0.0464 (16) | 0.000 | 0.0061 (12) | 0.000 |
C81 | 0.056 (2) | 0.076 (3) | 0.0467 (19) | 0.000 | 0.0032 (15) | 0.000 |
C9 | 0.0302 (14) | 0.0503 (18) | 0.0501 (17) | 0.000 | 0.0037 (12) | 0.000 |
C10 | 0.0438 (16) | 0.0475 (18) | 0.0475 (17) | 0.000 | 0.0095 (13) | 0.000 |
Geometric parameters (Å, º) top
O1—C2 | 1.311 (4) | C41—H41F | 0.977 (11) |
O1—C9 | 1.409 (3) | C42—C41i | 1.131 (15) |
O2—C2 | 1.180 (4) | C42—C3i | 1.534 (11) |
O6—C6 | 1.378 (3) | C42—H42A | 0.970 (7) |
O6—H6 | 0.88 (5) | C42—H42B | 0.957 (9) |
C2—C3 | 1.520 (6) | C42—H42C | 0.946 (16) |
C2—C3i | 1.520 (6) | C42—H42D | 0.945 (10) |
C3—C3i | 1.445 (13) | C42—H42E | 0.958 (11) |
C3—C42i | 1.534 (11) | C42—H42F | 0.969 (12) |
C3—C4 | 1.561 (6) | C5—C6 | 1.391 (4) |
C3—H3A | 0.97 (5) | C5—C10 | 1.403 (4) |
C3—H3B | 1.16 (5) | C5—C51 | 1.512 (5) |
C4—C42 | 1.480 (10) | C51—H51A | 0.99 (8) |
C4—C42i | 1.480 (10) | C51—H51C | 0.88 (4) |
C4—C10 | 1.536 (4) | C6—C7 | 1.388 (4) |
C4—C3i | 1.561 (6) | C7—C8 | 1.392 (4) |
C4—C41 | 1.587 (10) | C7—C71 | 1.505 (4) |
C4—C41i | 1.587 (10) | C71—H71A | 0.94 (4) |
C41—C42i | 1.131 (15) | C71—H71B | 0.97 (3) |
C41—C41i | 1.92 (3) | C8—C9 | 1.390 (4) |
C41—H41A | 0.984 (13) | C8—C81 | 1.502 (4) |
C41—H41B | 0.958 (8) | C81—H81A | 0.87 (5) |
C41—H41C | 0.951 (8) | C81—H81C | 0.97 (3) |
C41—H41D | 0.945 (10) | C9—C10 | 1.379 (4) |
C41—H41E | 0.971 (10) | | |
| | | |
C2—O1—C9 | 123.4 (3) | C42i—C41—H41F | 108.8 (12) |
C6—O6—H6 | 111 (3) | C4—C41—H41F | 109.3 (5) |
O2—C2—O1 | 120.5 (4) | C41i—C41—H41F | 111.5 (6) |
O2—C2—C3 | 121.5 (3) | H41A—C41—H41F | 55.0 (7) |
O1—C2—C3 | 110.2 (3) | H41B—C41—H41F | 55.8 (5) |
O2—C2—C3i | 121.5 (3) | H41C—C41—H41F | 139.7 (11) |
O1—C2—C3i | 110.2 (3) | H41D—C41—H41F | 109.3 (8) |
C3—C2—C3i | 56.8 (5) | H41E—C41—H41F | 107.2 (13) |
C3i—C3—C2 | 61.6 (3) | C41i—C42—C4 | 73.5 (10) |
C3i—C3—C42i | 115.6 (6) | C41i—C42—C3i | 132.3 (13) |
C2—C3—C42i | 159.3 (4) | C4—C42—C3i | 62.4 (4) |
C3i—C3—C4 | 62.4 (3) | C41i—C42—H42A | 84.9 (12) |
C2—C3—C4 | 109.5 (4) | C4—C42—H42A | 108.3 (9) |
C42i—C3—C4 | 57.1 (5) | C3i—C42—H42A | 92.2 (6) |
C3i—C3—H3A | 82 (3) | C41i—C42—H42B | 52.8 (9) |
C2—C3—H3A | 100 (3) | C4—C42—H42B | 109.1 (10) |
C42i—C3—H3A | 100 (3) | C3i—C42—H42B | 158.9 (8) |
C4—C3—H3A | 111 (3) | H42A—C42—H42B | 108.9 (9) |
C3i—C3—H3B | 161 (2) | C41i—C42—H42C | 162.1 (11) |
C2—C3—H3B | 113 (3) | C4—C42—H42C | 109.7 (7) |
C42i—C3—H3B | 62 (3) | C3i—C42—H42C | 59.4 (6) |
C4—C3—H3B | 106 (3) | H42A—C42—H42C | 109.8 (11) |
H3A—C3—H3B | 117 (4) | H42B—C42—H42C | 111.0 (11) |
C42—C4—C42i | 138.7 (8) | C41i—C42—H42D | 104.9 (10) |
C42—C4—C10 | 110.4 (4) | C4—C42—H42D | 109.8 (5) |
C42i—C4—C10 | 110.4 (4) | C3i—C42—H42D | 106.1 (10) |
C42—C4—C3i | 60.5 (6) | H42A—C42—H42D | 141.9 (11) |
C42i—C4—C3i | 112.0 (5) | H42B—C42—H42D | 56.8 (4) |
C10—C4—C3i | 106.4 (3) | H42C—C42—H42D | 57.2 (8) |
C42—C4—C3 | 112.0 (5) | C41i—C42—H42E | 140.1 (13) |
C42i—C4—C3 | 60.5 (6) | C4—C42—H42E | 109.0 (6) |
C10—C4—C3 | 106.4 (3) | C3i—C42—H42E | 51.8 (5) |
C3i—C4—C3 | 55.1 (5) | H42A—C42—H42E | 56.0 (4) |
C42—C4—C41 | 113.7 (7) | H42B—C42—H42E | 141.9 (10) |
C42i—C4—C41 | 43.1 (6) | H42C—C42—H42E | 56.8 (8) |
C10—C4—C41 | 112.0 (4) | H42D—C42—H42E | 110.9 (16) |
C3i—C4—C41 | 139.8 (4) | C41i—C42—H42F | 39.9 (6) |
C3—C4—C41 | 101.8 (4) | C4—C42—H42F | 108.4 (12) |
C42—C4—C41i | 43.1 (6) | C3i—C42—H42F | 143.6 (8) |
C42i—C4—C41i | 113.7 (7) | H42A—C42—H42F | 55.6 (6) |
C10—C4—C41i | 112.0 (4) | H42B—C42—H42F | 56.1 (6) |
C3i—C4—C41i | 101.8 (4) | H42C—C42—H42F | 141.9 (11) |
C3—C4—C41i | 139.8 (4) | H42D—C42—H42F | 110.0 (8) |
C41—C4—C41i | 74.5 (9) | H42E—C42—H42F | 108.9 (6) |
C42i—C41—C4 | 63.4 (6) | C6—C5—C10 | 118.7 (3) |
C42i—C41—C41i | 112.1 (9) | C6—C5—C51 | 116.7 (3) |
C4—C41—C41i | 52.8 (4) | C10—C5—C51 | 124.7 (3) |
C42i—C41—H41A | 62.1 (8) | C5—C51—H51A | 106 (4) |
C4—C41—H41A | 108.9 (6) | C5—C51—H51C | 114 (2) |
C41i—C41—H41A | 155.5 (4) | H51A—C51—H51C | 109 (3) |
C42i—C41—H41B | 162.1 (11) | O6—C6—C7 | 121.2 (3) |
C4—C41—H41B | 110.5 (8) | O6—C6—C5 | 115.3 (3) |
C41i—C41—H41B | 70.6 (8) | C7—C6—C5 | 123.5 (2) |
H41A—C41—H41B | 107.7 (11) | C6—C7—C8 | 118.2 (3) |
C42i—C41—H41C | 87.3 (8) | C6—C7—C71 | 120.3 (3) |
C4—C41—H41C | 111.0 (9) | C8—C7—C71 | 121.5 (3) |
C41i—C41—H41C | 94.7 (8) | C7—C71—H71A | 114 (3) |
H41A—C41—H41C | 108.2 (10) | C7—C71—H71B | 112.6 (17) |
H41B—C41—H41C | 110.4 (8) | H71A—C71—H71B | 107 (2) |
C42i—C41—H41D | 140.7 (12) | C9—C8—C7 | 117.6 (3) |
C4—C41—H41D | 111.4 (11) | C9—C8—C81 | 120.6 (3) |
C41i—C41—H41D | 61.0 (7) | C7—C8—C81 | 121.8 (3) |
H41A—C41—H41D | 139.7 (10) | C8—C81—H81A | 115 (3) |
H41B—C41—H41D | 56.8 (5) | C8—C81—H81C | 115.9 (18) |
H41C—C41—H41D | 57.0 (5) | H81A—C81—H81C | 102 (3) |
C42i—C41—H41E | 48.7 (6) | C10—C9—C8 | 125.2 (2) |
C4—C41—H41E | 109.7 (7) | C10—C9—O1 | 122.2 (2) |
C41i—C41—H41E | 141.1 (7) | C8—C9—O1 | 112.6 (2) |
H41A—C41—H41E | 55.2 (7) | C9—C10—C5 | 116.8 (3) |
H41B—C41—H41E | 139.6 (11) | C9—C10—C4 | 117.5 (3) |
H41C—C41—H41E | 56.2 (4) | C5—C10—C4 | 125.7 (3) |
H41D—C41—H41E | 109.9 (7) | | |
| | | |
C9—O1—C2—O2 | 180.0 | C10—C4—C42—C3i | −97.8 (4) |
C9—O1—C2—C3 | 30.4 (3) | C3—C4—C42—C3i | 20.6 (5) |
C9—O1—C2—C3i | −30.4 (3) | C41—C4—C42—C3i | 135.3 (5) |
O2—C2—C3—C3i | 109.3 (3) | C41i—C4—C42—C3i | 161.4 (9) |
O1—C2—C3—C3i | −101.5 (2) | C10—C5—C6—O6 | 180.0 |
O2—C2—C3—C42i | −163.0 (19) | C51—C5—C6—O6 | 0.0 |
O1—C2—C3—C42i | −14 (2) | C10—C5—C6—C7 | 0.0 |
C3i—C2—C3—C42i | 88 (2) | C51—C5—C6—C7 | 180.0 |
O2—C2—C3—C4 | 150.8 (3) | O6—C6—C7—C8 | 180.0 |
O1—C2—C3—C4 | −60.0 (4) | C5—C6—C7—C8 | 0.0 |
C3i—C2—C3—C4 | 41.5 (4) | O6—C6—C7—C71 | 0.0 |
C3i—C3—C4—C42 | −21.9 (5) | C5—C6—C7—C71 | 180.0 |
C2—C3—C4—C42 | −63.0 (7) | C6—C7—C8—C9 | 0.0 |
C42i—C3—C4—C42 | 134.7 (10) | C71—C7—C8—C9 | 180.0 |
C3i—C3—C4—C42i | −156.6 (5) | C6—C7—C8—C81 | 180.0 |
C2—C3—C4—C42i | 162.3 (6) | C71—C7—C8—C81 | 0.0 |
C3i—C3—C4—C10 | 98.83 (18) | C7—C8—C9—C10 | 0.0 |
C2—C3—C4—C10 | 57.7 (4) | C81—C8—C9—C10 | 180.0 |
C42i—C3—C4—C10 | −104.6 (5) | C7—C8—C9—O1 | 180.0 |
C2—C3—C4—C3i | −41.1 (4) | C81—C8—C9—O1 | 0.0 |
C42i—C3—C4—C3i | 156.6 (5) | C2—O1—C9—C10 | 0.0 |
C3i—C3—C4—C41 | −143.7 (5) | C2—O1—C9—C8 | 180.0 |
C2—C3—C4—C41 | 175.1 (5) | C8—C9—C10—C5 | 0.0 |
C42i—C3—C4—C41 | 12.9 (7) | O1—C9—C10—C5 | 180.0 |
C3i—C3—C4—C41i | −63.9 (7) | C8—C9—C10—C4 | 180.0 |
C2—C3—C4—C41i | −105.1 (8) | O1—C9—C10—C4 | 0.0 |
C42i—C3—C4—C41i | 92.7 (9) | C6—C5—C10—C9 | 0.0 |
C42—C4—C41—C42i | −137.1 (8) | C51—C5—C10—C9 | 180.0 |
C10—C4—C41—C42i | 96.8 (6) | C6—C5—C10—C4 | 180.0 |
C3i—C4—C41—C42i | −65.3 (11) | C51—C5—C10—C4 | 0.0 |
C3—C4—C41—C42i | −16.5 (8) | C42—C4—C10—C9 | 92.9 (6) |
C41i—C4—C41—C42i | −155.3 (5) | C42i—C4—C10—C9 | −92.9 (6) |
C42—C4—C41—C41i | 18.2 (4) | C3i—C4—C10—C9 | 28.8 (3) |
C42i—C4—C41—C41i | 155.3 (5) | C3—C4—C10—C9 | −28.8 (3) |
C10—C4—C41—C41i | −107.9 (4) | C41—C4—C10—C9 | −139.3 (4) |
C3i—C4—C41—C41i | 90.0 (7) | C41i—C4—C10—C9 | 139.3 (4) |
C3—C4—C41—C41i | 138.8 (4) | C42—C4—C10—C5 | −87.1 (6) |
C42i—C4—C42—C41i | −71.0 (15) | C42i—C4—C10—C5 | 87.1 (6) |
C10—C4—C42—C41i | 100.8 (8) | C3i—C4—C10—C5 | −151.2 (3) |
C3i—C4—C42—C41i | −161.4 (9) | C3—C4—C10—C5 | 151.2 (3) |
C3—C4—C42—C41i | −140.8 (7) | C41—C4—C10—C5 | 40.7 (4) |
C41—C4—C42—C41i | −26.1 (7) | C41i—C4—C10—C5 | −40.7 (4) |
C42i—C4—C42—C3i | 90.4 (15) | | |
Symmetry code: (i) x, −y+1/2, z. |
(a319) 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin
top
Crystal data top
C14H18O3 | V = 646.16 (13) Å3 |
Mr = 234.28 | Z = 2 |
P21/m, monoclinic | F(000) = 252 |
a = 9.753 (1) Å | Dx = 1.204 Mg m−3 |
b = 6.941 (1) Å | Cu Kα radiation, λ = 1.54178 Å |
c = 9.573 (1) Å | µ = 0.68 mm−1 |
α = 90° | T = 317 K |
β = 94.38 (1)° | , colourlees |
γ = 90° | 0.35 × 0.25 × 0.12 mm |
Data collection top
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 57.5°, θmin = 4.6° |
1035 measured reflections | h = −10→10 |
975 independent reflections | k = −7→0 |
804 reflections with I > 2σ(I) | l = 0→10 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.134 | w = 1/[σ2(Fo2) + (0.0815P)2 + 0.1245P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.407 |
975 reflections | Δρmax = 0.19 e Å−3 |
164 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.047 (5) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.10325 (17) | 0.2500 | 0.4956 (2) | 0.0706 (7) | |
O2 | −0.1145 (2) | 0.2500 | 0.5232 (3) | 0.1082 (11) | |
O6 | 0.64967 (18) | 0.2500 | 0.6761 (2) | 0.0645 (7) | |
H6 | 0.711 (4) | 0.2500 | 0.609 (4) | 0.102 (13)* | |
C2 | −0.0004 (3) | 0.2500 | 0.5741 (3) | 0.0713 (10) | |
C3 | 0.0382 (4) | 0.3550 (8) | 0.7120 (5) | 0.0736 (13) | 0.50 |
H3A | −0.047 (5) | 0.331 (6) | 0.762 (5) | 0.095 (16)* | 0.50 |
H3B | 0.069 (4) | 0.507 (6) | 0.699 (5) | 0.063 (12)* | 0.50 |
C4 | 0.1624 (3) | 0.2500 | 0.7907 (3) | 0.0684 (9) | |
C41 | 0.1955 (8) | 0.3891 (15) | 0.9212 (6) | 0.120 (3) | 0.50 |
H41A | 0.2178 | 0.5171 | 0.8874 | 0.08 (9)* | 0.25 |
H41B | 0.2735 | 0.3421 | 0.9784 | 0.040 (17)* | 0.25 |
H41C | 0.1178 | 0.3993 | 0.9754 | 0.06 (2)* | 0.25 |
H41D | 0.1882 | 0.3219 | 1.0068 | 0.14 (5)* | 0.25 |
H41E | 0.1326 | 0.4969 | 0.9157 | 0.27 (16)* | 0.25 |
H41F | 0.2883 | 0.4397 | 0.9187 | 0.38 (18)* | 0.25 |
C42 | 0.1270 (6) | 0.0495 (13) | 0.8282 (10) | 0.116 (3) | 0.50 |
H42A | 0.0552 | 0.0551 | 0.8925 | 0.034 (15)* | 0.25 |
H42B | 0.2075 | −0.0084 | 0.8767 | 0.07 (8)* | 0.25 |
H42C | 0.0986 | −0.0199 | 0.7478 | 0.4 (2)* | 0.25 |
H42D | 0.1856 | −0.0372 | 0.7855 | 2 (2)* | 0.25 |
H42E | 0.0333 | 0.0263 | 0.8013 | 0.10 (4)* | 0.25 |
H42F | 0.1423 | 0.0377 | 0.9302 | 0.09 (4)* | 0.25 |
C5 | 0.4203 (2) | 0.2500 | 0.7319 (3) | 0.0478 (7) | |
C51 | 0.4816 (4) | 0.2500 | 0.8819 (4) | 0.0834 (12) | |
H51A | 0.578 (7) | 0.2500 | 0.870 (6) | 0.19 (3)* | |
H51C | 0.448 (3) | 0.153 (5) | 0.933 (3) | 0.147 (14)* | |
C6 | 0.5132 (2) | 0.2500 | 0.6289 (3) | 0.0444 (7) | |
C7 | 0.4731 (2) | 0.2500 | 0.4857 (3) | 0.0438 (7) | |
C71 | 0.5796 (3) | 0.2500 | 0.3804 (4) | 0.0579 (8) | |
H71A | 0.541 (4) | 0.2500 | 0.288 (5) | 0.111 (14)* | |
H71B | 0.642 (3) | 0.146 (4) | 0.394 (2) | 0.098 (8)* | |
C8 | 0.3329 (2) | 0.2500 | 0.4446 (2) | 0.0434 (7) | |
C81 | 0.2807 (3) | 0.2500 | 0.2932 (3) | 0.0595 (9) | |
H81A | 0.176 (7) | 0.2500 | 0.293 (6) | 0.057 (16)* | 0.50 |
H81C | 0.314 (4) | 0.128 (6) | 0.240 (4) | 0.050 (9)* | 0.50 |
H81D | 0.351 (10) | 0.2500 | 0.222 (9) | 0.12 (3)* | 0.50 |
H81E | 0.217 (4) | 0.142 (7) | 0.266 (4) | 0.061 (11)* | 0.50 |
C9 | 0.2418 (2) | 0.2500 | 0.5487 (3) | 0.0438 (7) | |
C10 | 0.2790 (2) | 0.2500 | 0.6918 (2) | 0.0462 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0314 (10) | 0.1178 (19) | 0.0626 (12) | 0.000 | 0.0039 (8) | 0.000 |
O2 | 0.0335 (13) | 0.167 (3) | 0.124 (2) | 0.000 | 0.0099 (12) | 0.000 |
O6 | 0.0357 (11) | 0.0765 (14) | 0.0795 (14) | 0.000 | −0.0070 (9) | 0.000 |
C2 | 0.0321 (16) | 0.101 (2) | 0.082 (2) | 0.000 | 0.0116 (14) | 0.000 |
C3 | 0.048 (2) | 0.103 (4) | 0.072 (3) | 0.018 (2) | 0.0239 (19) | 0.002 (3) |
C4 | 0.0557 (18) | 0.097 (2) | 0.0552 (17) | 0.000 | 0.0202 (13) | 0.000 |
C41 | 0.095 (4) | 0.211 (9) | 0.055 (3) | 0.061 (5) | 0.016 (3) | −0.029 (4) |
C42 | 0.075 (4) | 0.149 (6) | 0.130 (6) | 0.013 (4) | 0.047 (4) | 0.082 (6) |
C5 | 0.0477 (15) | 0.0452 (15) | 0.0498 (14) | 0.000 | −0.0006 (11) | 0.000 |
C51 | 0.073 (2) | 0.121 (3) | 0.0538 (18) | 0.000 | −0.0077 (16) | 0.000 |
C6 | 0.0311 (13) | 0.0400 (14) | 0.0614 (15) | 0.000 | −0.0018 (10) | 0.000 |
C7 | 0.0371 (13) | 0.0369 (14) | 0.0581 (15) | 0.000 | 0.0084 (11) | 0.000 |
C71 | 0.0447 (16) | 0.061 (2) | 0.071 (2) | 0.000 | 0.0211 (14) | 0.000 |
C8 | 0.0397 (14) | 0.0419 (14) | 0.0491 (14) | 0.000 | 0.0070 (10) | 0.000 |
C81 | 0.0531 (18) | 0.075 (2) | 0.0497 (16) | 0.000 | 0.0007 (13) | 0.000 |
C9 | 0.0293 (12) | 0.0509 (15) | 0.0512 (14) | 0.000 | 0.0030 (10) | 0.000 |
C10 | 0.0415 (14) | 0.0486 (15) | 0.0492 (14) | 0.000 | 0.0084 (11) | 0.000 |
Geometric parameters (Å, º) top
O1—C2 | 1.305 (3) | C42—C41i | 1.153 (11) |
O1—C9 | 1.407 (3) | C42—C3i | 1.510 (9) |
O2—C2 | 1.180 (4) | C42—H42A | 0.968 (6) |
O6—C6 | 1.373 (3) | C42—H42B | 0.968 (7) |
O6—H6 | 0.92 (4) | C42—H42C | 0.932 (12) |
C2—C3 | 1.530 (6) | C42—H42D | 0.944 (8) |
C2—C3i | 1.530 (6) | C42—H42E | 0.944 (8) |
C3—C3i | 1.458 (12) | C42—H42F | 0.980 (9) |
C3—C42i | 1.510 (9) | C5—C6 | 1.389 (4) |
C3—C4 | 1.558 (5) | C5—C10 | 1.403 (3) |
C3—H3A | 1.01 (5) | C5—C51 | 1.513 (4) |
C3—H3B | 1.11 (4) | C51—H51A | 0.96 (7) |
C4—C42i | 1.485 (8) | C51—H51C | 0.91 (3) |
C4—C42 | 1.485 (8) | C6—C7 | 1.396 (4) |
C4—C10 | 1.534 (3) | C7—C8 | 1.393 (3) |
C4—C3i | 1.558 (5) | C7—C71 | 1.503 (3) |
C4—C41 | 1.593 (8) | C71—H71A | 0.93 (4) |
C4—C41i | 1.593 (8) | C71—H71B | 0.95 (3) |
C41—C42i | 1.153 (11) | C8—C9 | 1.384 (3) |
C41—C41i | 1.93 (2) | C8—C81 | 1.499 (4) |
C41—H41A | 0.976 (11) | C81—H81A | 1.02 (6) |
C41—H41B | 0.959 (7) | C81—H81C | 1.05 (4) |
C41—H41C | 0.954 (6) | C81—H81D | 1.00 (9) |
C41—H41D | 0.950 (8) | C81—H81E | 0.99 (4) |
C41—H41E | 0.966 (8) | C9—C10 | 1.391 (3) |
C41—H41F | 0.972 (9) | | |
| | | |
C2—O1—C9 | 123.9 (2) | H41A—C41—H41F | 55.4 (6) |
C6—O6—H6 | 116 (3) | H41B—C41—H41F | 55.9 (4) |
O2—C2—O1 | 120.7 (3) | H41C—C41—H41F | 140.1 (9) |
O2—C2—C3 | 121.2 (2) | H41D—C41—H41F | 109.3 (7) |
O1—C2—C3 | 110.3 (2) | H41E—C41—H41F | 107.9 (10) |
O2—C2—C3i | 121.2 (2) | C41i—C42—C4 | 73.1 (8) |
O1—C2—C3i | 110.3 (2) | C41i—C42—C3i | 132.3 (10) |
C3—C2—C3i | 56.9 (4) | C4—C42—C3i | 62.7 (3) |
C3i—C3—C42i | 116.0 (5) | C41i—C42—H42A | 84.2 (9) |
C3i—C3—C2 | 61.5 (2) | C4—C42—H42A | 108.0 (7) |
C42i—C3—C2 | 159.1 (3) | C3i—C42—H42A | 92.8 (5) |
C3i—C3—C4 | 62.1 (2) | C41i—C42—H42B | 51.9 (7) |
C42i—C3—C4 | 57.9 (4) | C4—C42—H42B | 108.1 (7) |
C2—C3—C4 | 109.0 (3) | C3i—C42—H42B | 159.1 (6) |
C3i—C3—H3A | 80 (3) | H42A—C42—H42B | 108.1 (7) |
C42i—C3—H3A | 100 (3) | C41i—C42—H42C | 161.3 (9) |
C2—C3—H3A | 100 (3) | C4—C42—H42C | 110.2 (5) |
C4—C3—H3A | 110 (3) | C3i—C42—H42C | 60.0 (5) |
C3i—C3—H3B | 162.4 (19) | H42A—C42—H42C | 111.2 (8) |
C42i—C3—H3B | 61 (2) | H42B—C42—H42C | 111.2 (9) |
C2—C3—H3B | 114 (2) | C41i—C42—H42D | 103.6 (8) |
C4—C3—H3B | 107 (2) | C4—C42—H42D | 109.5 (4) |
H3A—C3—H3B | 117 (3) | C3i—C42—H42D | 107.1 (8) |
C42i—C4—C42 | 139.3 (6) | H42A—C42—H42D | 142.4 (8) |
C42i—C4—C10 | 110.2 (3) | H42B—C42—H42D | 56.5 (3) |
C42—C4—C10 | 110.2 (3) | H42C—C42—H42D | 57.7 (6) |
C42i—C4—C3i | 111.7 (4) | C41i—C42—H42E | 139.9 (10) |
C42—C4—C3i | 59.5 (4) | C4—C42—H42E | 109.4 (5) |
C10—C4—C3i | 106.7 (2) | C3i—C42—H42E | 52.0 (4) |
C42i—C4—C3 | 59.5 (4) | H42A—C42—H42E | 56.5 (3) |
C42—C4—C3 | 111.7 (4) | H42B—C42—H42E | 142.4 (8) |
C10—C4—C3 | 106.7 (2) | H42C—C42—H42E | 57.7 (6) |
C3i—C4—C3 | 55.8 (4) | H42D—C42—H42E | 112.3 (12) |
C42i—C4—C41 | 43.8 (5) | C41i—C42—H42F | 39.3 (5) |
C42—C4—C41 | 114.6 (6) | C4—C42—H42F | 107.4 (9) |
C10—C4—C41 | 111.6 (3) | C3i—C42—H42F | 143.6 (7) |
C3i—C4—C41 | 140.0 (4) | H42A—C42—H42F | 55.4 (4) |
C3—C4—C41 | 101.5 (3) | H42B—C42—H42F | 55.3 (5) |
C42i—C4—C41i | 114.6 (6) | H42C—C42—H42F | 142.5 (8) |
C42—C4—C41i | 43.8 (5) | H42D—C42—H42F | 109.1 (6) |
C10—C4—C41i | 111.6 (3) | H42E—C42—H42F | 109.1 (5) |
C3i—C4—C41i | 101.5 (3) | C6—C5—C10 | 119.1 (2) |
C3—C4—C41i | 140.0 (4) | C6—C5—C51 | 116.2 (3) |
C41—C4—C41i | 74.6 (7) | C10—C5—C51 | 124.6 (3) |
C42i—C41—C4 | 63.1 (5) | C5—C51—H51A | 102 (4) |
C42i—C41—C41i | 111.7 (7) | C5—C51—H51C | 112 (2) |
C4—C41—C41i | 52.7 (3) | H51A—C51—H51C | 118 (3) |
C42i—C41—H41A | 62.5 (6) | O6—C6—C5 | 115.8 (2) |
C4—C41—H41A | 109.1 (4) | O6—C6—C7 | 121.0 (2) |
C41i—C41—H41A | 155.5 (3) | C5—C6—C7 | 123.2 (2) |
C42i—C41—H41B | 162.4 (8) | C8—C7—C6 | 118.2 (2) |
C4—C41—H41B | 110.2 (6) | C8—C7—C71 | 121.6 (2) |
C41i—C41—H41B | 70.1 (6) | C6—C7—C71 | 120.2 (2) |
H41A—C41—H41B | 108.2 (9) | C7—C71—H71A | 113 (3) |
C42i—C41—H41C | 87.4 (6) | C7—C71—H71B | 111.8 (15) |
C4—C41—H41C | 110.5 (8) | H71A—C71—H71B | 110 (2) |
C41i—C41—H41C | 94.2 (6) | C9—C8—C7 | 117.8 (2) |
H41A—C41—H41C | 108.7 (8) | C9—C8—C81 | 120.4 (2) |
H41B—C41—H41C | 110.1 (6) | C7—C8—C81 | 121.8 (2) |
C42i—C41—H41D | 140.4 (10) | C8—C81—H81A | 106 (3) |
C4—C41—H41D | 110.7 (9) | C8—C81—H81C | 112 (2) |
C41i—C41—H41D | 60.6 (5) | H81A—C81—H81C | 110 (3) |
H41A—C41—H41D | 140.1 (8) | C8—C81—H81D | 117 (5) |
H41B—C41—H41D | 56.6 (4) | H81A—C81—H81D | 137 (6) |
H41C—C41—H41D | 56.8 (4) | H81C—C81—H81D | 55 (2) |
C42i—C41—H41E | 49.0 (4) | C8—C81—H81E | 114 (2) |
C4—C41—H41E | 109.7 (5) | H81A—C81—H81E | 53 (2) |
C41i—C41—H41E | 140.7 (6) | H81C—C81—H81E | 59 (3) |
H41A—C41—H41E | 55.6 (5) | H81D—C81—H81E | 106 (4) |
H41B—C41—H41E | 140.1 (9) | C8—C9—C10 | 125.2 (2) |
H41C—C41—H41E | 56.2 (3) | C8—C9—O1 | 113.1 (2) |
H41D—C41—H41E | 109.8 (5) | C10—C9—O1 | 121.8 (2) |
C42i—C41—H41F | 109.4 (9) | C9—C10—C5 | 116.5 (2) |
C4—C41—H41F | 109.4 (4) | C9—C10—C4 | 117.3 (2) |
C41i—C41—H41F | 111.1 (5) | C5—C10—C4 | 126.2 (2) |
| | | |
C9—O1—C2—O2 | 180.0 | C10—C4—C42—C3i | −97.9 (3) |
C9—O1—C2—C3 | 30.5 (2) | C3—C4—C42—C3i | 20.5 (4) |
C9—O1—C2—C3i | −30.5 (2) | C41—C4—C42—C3i | 135.1 (4) |
O2—C2—C3—C3i | 109.2 (3) | C41i—C4—C42—C3i | 161.5 (7) |
O1—C2—C3—C3i | −101.54 (17) | C10—C5—C6—O6 | 180.0 |
O2—C2—C3—C42i | −162.0 (15) | C51—C5—C6—O6 | 0.0 |
O1—C2—C3—C42i | −12.7 (17) | C10—C5—C6—C7 | 0.0 |
C3i—C2—C3—C42i | 88.9 (16) | C51—C5—C6—C7 | 180.0 |
O2—C2—C3—C4 | 150.6 (2) | O6—C6—C7—C8 | 180.0 |
O1—C2—C3—C4 | −60.1 (3) | C5—C6—C7—C8 | 0.0 |
C3i—C2—C3—C4 | 41.5 (3) | O6—C6—C7—C71 | 0.0 |
C3i—C3—C4—C42i | −156.8 (4) | C5—C6—C7—C71 | 180.0 |
C2—C3—C4—C42i | 162.0 (5) | C6—C7—C8—C9 | 0.0 |
C3i—C3—C4—C42 | −21.4 (4) | C71—C7—C8—C9 | 180.0 |
C42i—C3—C4—C42 | 135.4 (8) | C6—C7—C8—C81 | 180.0 |
C2—C3—C4—C42 | −62.6 (5) | C71—C7—C8—C81 | 0.0 |
C3i—C3—C4—C10 | 99.14 (16) | C7—C8—C9—C10 | 0.0 |
C42i—C3—C4—C10 | −104.0 (4) | C81—C8—C9—C10 | 180.0 |
C2—C3—C4—C10 | 57.9 (3) | C7—C8—C9—O1 | 180.0 |
C42i—C3—C4—C3i | 156.8 (4) | C81—C8—C9—O1 | 0.0 |
C2—C3—C4—C3i | −41.2 (3) | C2—O1—C9—C8 | 180.0 |
C3i—C3—C4—C41 | −143.9 (4) | C2—O1—C9—C10 | 0.0 |
C42i—C3—C4—C41 | 13.0 (6) | C8—C9—C10—C5 | 0.0 |
C2—C3—C4—C41 | 174.9 (4) | O1—C9—C10—C5 | 180.0 |
C3i—C3—C4—C41i | −64.1 (6) | C8—C9—C10—C4 | 180.0 |
C42i—C3—C4—C41i | 92.7 (7) | O1—C9—C10—C4 | 0.0 |
C2—C3—C4—C41i | −105.3 (6) | C6—C5—C10—C9 | 0.0 |
C42—C4—C41—C42i | −136.6 (7) | C51—C5—C10—C9 | 180.0 |
C10—C4—C41—C42i | 97.1 (5) | C6—C5—C10—C4 | 180.0 |
C3i—C4—C41—C42i | −65.6 (9) | C51—C5—C10—C4 | 0.0 |
C3—C4—C41—C42i | −16.2 (6) | C42i—C4—C10—C9 | −92.2 (5) |
C41i—C4—C41—C42i | −155.2 (4) | C42—C4—C10—C9 | 92.2 (5) |
C42i—C4—C41—C41i | 155.2 (4) | C3i—C4—C10—C9 | 29.2 (2) |
C42—C4—C41—C41i | 18.6 (3) | C3—C4—C10—C9 | −29.2 (2) |
C10—C4—C41—C41i | −107.6 (3) | C41—C4—C10—C9 | −139.3 (3) |
C3i—C4—C41—C41i | 89.7 (6) | C41i—C4—C10—C9 | 139.3 (3) |
C3—C4—C41—C41i | 139.1 (3) | C42i—C4—C10—C5 | 87.8 (5) |
C42i—C4—C42—C41i | −73.2 (11) | C42—C4—C10—C5 | −87.8 (5) |
C10—C4—C42—C41i | 100.6 (7) | C3i—C4—C10—C5 | −150.8 (2) |
C3i—C4—C42—C41i | −161.5 (7) | C3—C4—C10—C5 | 150.8 (2) |
C3—C4—C42—C41i | −141.0 (5) | C41—C4—C10—C5 | 40.7 (3) |
C41—C4—C42—C41i | −26.4 (5) | C41i—C4—C10—C5 | −40.7 (3) |
C42i—C4—C42—C3i | 88.3 (12) | | |
Symmetry code: (i) x, −y+1/2, z. |
(a329) 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin
top
Crystal data top
C14H18O3 | V = 647.07 (18) Å3 |
Mr = 234.28 | Z = 2 |
P21/m, monoclinic | F(000) = 252 |
a = 9.756 (1) Å | Dx = 1.202 Mg m−3 |
b = 6.947 (1) Å | Cu Kα radiation, λ = 1.54178 Å |
c = 9.575 (2) Å | µ = 0.68 mm−1 |
α = 90° | T = 328 K |
β = 94.36 (2)° | , colourlees |
γ = 90° | 0.35 × 0.25 × 0.12 mm |
Data collection top
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 55.1°, θmin = 4.6° |
955 measured reflections | h = −10→10 |
899 independent reflections | k = −7→0 |
742 reflections with I > 2σ(I) | l = 0→10 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.161 | w = 1/[σ2(Fo2) + (0.0793P)2 + 0.1455P] where P = (Fo2 + 2Fc2)/3 |
S = 1.32 | (Δ/σ)max = 1.155 |
899 reflections | Δρmax = 0.21 e Å−3 |
159 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.045 (6) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.1034 (2) | 0.2500 | 0.4959 (3) | 0.0726 (10) | |
O2 | −0.1143 (3) | 0.2500 | 0.5229 (4) | 0.1117 (15) | |
O6 | 0.6494 (3) | 0.2500 | 0.6762 (3) | 0.0656 (9) | |
H6 | 0.711 (7) | 0.2500 | 0.621 (6) | 0.13 (2)* | |
C2 | −0.0001 (4) | 0.2500 | 0.5738 (5) | 0.0727 (13) | |
C3 | 0.0384 (5) | 0.3567 (10) | 0.7110 (6) | 0.0790 (19) | 0.50 |
H3A | −0.050 (7) | 0.350 (9) | 0.778 (7) | 0.12 (2)* | 0.50 |
H3B | 0.092 (4) | 0.525 (6) | 0.738 (4) | 0.034 (10)* | 0.50 |
C4 | 0.1626 (4) | 0.2500 | 0.7909 (4) | 0.0699 (13) | |
C41 | 0.1909 (8) | 0.3884 (17) | 0.9172 (7) | 0.114 (3) | 0.50 |
H41A | 0.2176 | 0.5173 | 0.8868 | 0.03 (4)* | 0.25 |
H41B | 0.2735 | 0.3429 | 0.9782 | 0.08 (4)* | 0.25 |
H41C | 0.1178 | 0.3996 | 0.9752 | 0.027 (18)* | 0.25 |
H41D | 0.1883 | 0.3226 | 1.0067 | 0.15 (7)* | 0.25 |
H41E | 0.1324 | 0.4970 | 0.9153 | 2 (4)* | 0.25 |
H41F | 0.2881 | 0.4403 | 0.9183 | 0.19 (8)* | 0.25 |
C42 | 0.1260 (10) | 0.0488 (13) | 0.8271 (11) | 0.103 (2)* | 0.50 |
H42A | 0.0560 | 0.0561 | 0.8935 | 0.09 (4)* | 0.25 |
H42B | 0.2083 | −0.0072 | 0.8775 | 0.11 (11)* | 0.25 |
H42C | 0.0991 | −0.0196 | 0.7489 | 2 (5)* | 0.25 |
H42D | 0.1863 | −0.0365 | 0.7865 | 2 (5)* | 0.25 |
H42E | 0.0340 | 0.0267 | 0.8024 | 0.4 (2)* | 0.25 |
H42F | 0.1431 | 0.0391 | 0.9310 | 0.08 (4)* | 0.25 |
C5 | 0.4201 (3) | 0.2500 | 0.7319 (3) | 0.0485 (9) | |
C51 | 0.4805 (6) | 0.2500 | 0.8829 (5) | 0.0858 (17) | |
H51A | 0.554 (10) | 0.2500 | 0.890 (9) | 0.20 (4)* | |
H51C | 0.439 (4) | 0.146 (6) | 0.939 (4) | 0.143 (16)* | |
C6 | 0.5136 (3) | 0.2500 | 0.6287 (4) | 0.0455 (9) | |
C7 | 0.4730 (3) | 0.2500 | 0.4858 (3) | 0.0430 (9) | |
C71 | 0.5796 (4) | 0.2500 | 0.3806 (5) | 0.0592 (12) | |
H71A | 0.535 (6) | 0.2500 | 0.291 (6) | 0.12 (2)* | |
H71B | 0.641 (3) | 0.150 (5) | 0.393 (3) | 0.098 (11)* | |
C8 | 0.3335 (3) | 0.2500 | 0.4449 (3) | 0.0443 (9) | |
C81 | 0.2805 (5) | 0.2500 | 0.2940 (4) | 0.0601 (12) | |
H81A | 0.189 (8) | 0.2500 | 0.287 (6) | 0.033 (17)* | 0.50 |
H81C | 0.306 (4) | 0.124 (7) | 0.241 (5) | 0.037 (11)* | 0.50 |
H81D | 0.340 (10) | 0.2500 | 0.250 (10) | 0.07 (3)* | 0.50 |
H81E | 0.215 (6) | 0.135 (8) | 0.258 (5) | 0.063 (14)* | 0.50 |
C9 | 0.2416 (3) | 0.2500 | 0.5493 (3) | 0.0445 (9) | |
C10 | 0.2791 (3) | 0.2500 | 0.6916 (3) | 0.0478 (10) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0348 (15) | 0.119 (2) | 0.0643 (16) | 0.000 | 0.0037 (12) | 0.000 |
O2 | 0.0345 (18) | 0.173 (4) | 0.128 (3) | 0.000 | 0.0113 (16) | 0.000 |
O6 | 0.0373 (15) | 0.0766 (18) | 0.0812 (19) | 0.000 | −0.0067 (13) | 0.000 |
C2 | 0.034 (2) | 0.105 (3) | 0.081 (3) | 0.000 | 0.0129 (19) | 0.000 |
C3 | 0.045 (3) | 0.120 (5) | 0.075 (3) | 0.022 (3) | 0.020 (2) | −0.001 (4) |
C4 | 0.062 (3) | 0.092 (3) | 0.058 (2) | 0.000 | 0.0213 (19) | 0.000 |
C41 | 0.097 (6) | 0.183 (9) | 0.065 (4) | 0.055 (6) | 0.034 (4) | −0.031 (5) |
C5 | 0.048 (2) | 0.047 (2) | 0.050 (2) | 0.000 | −0.0006 (16) | 0.000 |
C51 | 0.074 (3) | 0.127 (5) | 0.054 (2) | 0.000 | −0.008 (2) | 0.000 |
C6 | 0.0327 (18) | 0.0393 (19) | 0.063 (2) | 0.000 | −0.0036 (15) | 0.000 |
C7 | 0.0361 (18) | 0.0372 (18) | 0.056 (2) | 0.000 | 0.0092 (15) | 0.000 |
C71 | 0.044 (2) | 0.061 (3) | 0.075 (3) | 0.000 | 0.021 (2) | 0.000 |
C8 | 0.0423 (19) | 0.044 (2) | 0.0473 (19) | 0.000 | 0.0076 (14) | 0.000 |
C81 | 0.052 (3) | 0.078 (4) | 0.050 (2) | 0.000 | 0.002 (2) | 0.000 |
C9 | 0.0288 (17) | 0.053 (2) | 0.051 (2) | 0.000 | 0.0009 (14) | 0.000 |
C10 | 0.044 (2) | 0.049 (2) | 0.051 (2) | 0.000 | 0.0089 (15) | 0.000 |
Geometric parameters (Å, º) top
O1—C2 | 1.300 (4) | C42—C41i | 1.119 (12) |
O1—C9 | 1.405 (4) | C42—C3i | 1.501 (12) |
O2—C2 | 1.182 (5) | C42—H42A | 0.969 (9) |
O6—C6 | 1.367 (4) | C42—H42B | 0.984 (10) |
O6—H6 | 0.83 (6) | C42—H42C | 0.908 (11) |
C2—C3 | 1.530 (7) | C42—H42D | 0.939 (9) |
C2—C3i | 1.530 (7) | C42—H42E | 0.924 (10) |
C3—C3i | 1.483 (15) | C42—H42F | 0.999 (10) |
C3—C42i | 1.501 (12) | C5—C6 | 1.394 (5) |
C3—C4 | 1.569 (7) | C5—C10 | 1.400 (5) |
C3—H3A | 1.12 (7) | C5—C51 | 1.519 (5) |
C3—H3B | 1.30 (4) | C51—H51A | 0.72 (10) |
C4—C42i | 1.490 (9) | C51—H51C | 1.00 (4) |
C4—C42 | 1.490 (9) | C6—C7 | 1.395 (5) |
C4—C10 | 1.537 (5) | C7—C8 | 1.387 (4) |
C4—C3i | 1.569 (7) | C7—C71 | 1.503 (5) |
C4—C41 | 1.554 (9) | C71—H71A | 0.93 (6) |
C4—C41i | 1.554 (9) | C71—H71B | 0.92 (3) |
C41—C42i | 1.119 (12) | C8—C9 | 1.393 (4) |
C41—C41i | 1.92 (2) | C8—C81 | 1.498 (5) |
C41—H41A | 0.983 (12) | C81—H81A | 0.89 (7) |
C41—H41B | 1.009 (8) | C81—H81C | 1.05 (5) |
C41—H41C | 0.940 (7) | C81—H81D | 0.74 (10) |
C41—H41D | 0.973 (9) | C81—H81E | 1.06 (6) |
C41—H41E | 0.945 (9) | C9—C10 | 1.384 (5) |
C41—H41F | 1.014 (9) | | |
| | | |
C2—O1—C9 | 123.8 (3) | H41A—C41—H41F | 53.9 (6) |
C6—O6—H6 | 121 (4) | H41B—C41—H41F | 53.1 (4) |
O2—C2—O1 | 120.8 (4) | H41C—C41—H41F | 135.7 (9) |
O2—C2—C3 | 121.1 (3) | H41D—C41—H41F | 104.2 (7) |
O1—C2—C3 | 110.0 (3) | H41E—C41—H41F | 106.2 (11) |
O2—C2—C3i | 121.1 (3) | C41i—C42—C4 | 71.5 (8) |
O1—C2—C3i | 110.0 (3) | C41i—C42—C3i | 131.1 (10) |
C3—C2—C3i | 58.0 (5) | C4—C42—C3i | 63.3 (5) |
C3i—C3—C42i | 115.9 (5) | C41i—C42—H42A | 81.9 (9) |
C3i—C3—C2 | 61.0 (3) | C4—C42—H42A | 107.2 (7) |
C42i—C3—C2 | 159.5 (5) | C3i—C42—H42A | 94.1 (7) |
C3i—C3—C4 | 61.8 (3) | C41i—C42—H42B | 52.0 (8) |
C42i—C3—C4 | 58.0 (4) | C4—C42—H42B | 106.5 (8) |
C2—C3—C4 | 108.6 (4) | C3i—C42—H42B | 158.9 (9) |
C3i—C3—H3A | 88 (3) | H42A—C42—H42B | 106.7 (9) |
C42i—C3—H3A | 91 (3) | C41i—C42—H42C | 161.9 (12) |
C2—C3—H3A | 109 (3) | C4—C42—H42C | 111.0 (8) |
C4—C3—H3A | 108 (3) | C3i—C42—H42C | 60.4 (6) |
C3i—C3—H3B | 154.4 (18) | H42A—C42—H42C | 113.2 (10) |
C42i—C3—H3B | 42.5 (18) | H42B—C42—H42C | 111.8 (9) |
C2—C3—H3B | 132 (2) | C41i—C42—H42D | 103.3 (11) |
C4—C3—H3B | 92.7 (19) | C4—C42—H42D | 109.1 (7) |
H3A—C3—H3B | 104 (4) | C3i—C42—H42D | 108.0 (9) |
C42i—C4—C42 | 139.5 (7) | H42A—C42—H42D | 143.0 (10) |
C42i—C4—C10 | 110.2 (4) | H42B—C42—H42D | 56.1 (5) |
C42—C4—C10 | 110.2 (4) | H42C—C42—H42D | 58.6 (6) |
C42i—C4—C3i | 111.6 (5) | C41i—C42—H42E | 138.0 (11) |
C42—C4—C3i | 58.7 (5) | C4—C42—H42E | 109.9 (8) |
C10—C4—C3i | 106.2 (3) | C3i—C42—H42E | 52.8 (5) |
C42i—C4—C3 | 58.7 (5) | H42A—C42—H42E | 57.1 (5) |
C42—C4—C3 | 111.6 (5) | H42B—C42—H42E | 143.1 (10) |
C10—C4—C3 | 106.2 (3) | H42C—C42—H42E | 59.2 (7) |
C3i—C4—C3 | 56.4 (6) | H42D—C42—H42E | 114.6 (11) |
C42i—C4—C41 | 43.1 (5) | C41i—C42—H42F | 38.4 (5) |
C42—C4—C41 | 115.5 (6) | C4—C42—H42F | 105.7 (8) |
C10—C4—C41 | 112.7 (4) | C3i—C42—H42F | 144.1 (9) |
C3i—C4—C41 | 139.2 (4) | H42A—C42—H42F | 54.7 (5) |
C3—C4—C41 | 99.9 (4) | H42B—C42—H42F | 54.3 (6) |
C42i—C4—C41i | 115.5 (6) | H42C—C42—H42F | 143.3 (10) |
C42—C4—C41i | 43.1 (5) | H42D—C42—H42F | 108.0 (9) |
C10—C4—C41i | 112.7 (4) | H42E—C42—H42F | 109.2 (9) |
C3i—C4—C41i | 99.9 (4) | C6—C5—C10 | 119.1 (3) |
C3—C4—C41i | 139.2 (4) | C6—C5—C51 | 116.6 (4) |
C41—C4—C41i | 76.5 (8) | C10—C5—C51 | 124.3 (4) |
C42i—C41—C4 | 65.4 (6) | C5—C51—H51A | 114 (7) |
C42i—C41—C41i | 113.0 (7) | C5—C51—H51C | 112 (2) |
C4—C41—C41i | 51.8 (4) | H51A—C51—H51C | 113 (5) |
C42i—C41—H41A | 64.1 (8) | O6—C6—C5 | 115.7 (3) |
C4—C41—H41A | 111.6 (6) | O6—C6—C7 | 121.5 (3) |
C41i—C41—H41A | 155.7 (4) | C5—C6—C7 | 122.9 (3) |
C42i—C41—H41B | 161.4 (10) | C8—C7—C6 | 118.4 (3) |
C4—C41—H41B | 110.1 (7) | C8—C7—C71 | 121.7 (3) |
C41i—C41—H41B | 71.8 (6) | C6—C7—C71 | 119.9 (3) |
H41A—C41—H41B | 103.8 (9) | C7—C71—H71A | 109 (3) |
C42i—C41—H41C | 90.8 (8) | C7—C71—H71B | 113.0 (19) |
C4—C41—H41C | 114.4 (8) | H71A—C71—H71B | 112 (3) |
C41i—C41—H41C | 94.8 (7) | C7—C8—C9 | 118.0 (3) |
H41A—C41—H41C | 109.2 (9) | C7—C8—C81 | 122.2 (3) |
H41B—C41—H41C | 107.0 (7) | C9—C8—C81 | 119.9 (3) |
C42i—C41—H41D | 144.2 (10) | C8—C81—H81A | 110 (4) |
C4—C41—H41D | 112.3 (9) | C8—C81—H81C | 113 (2) |
C41i—C41—H41D | 62.0 (6) | H81A—C81—H81C | 104 (3) |
H41A—C41—H41D | 135.6 (9) | C8—C81—H81D | 108 (7) |
H41B—C41—H41D | 54.3 (5) | H81A—C81—H81D | 142 (8) |
H41C—C41—H41D | 56.5 (5) | H81C—C81—H81D | 60 (3) |
C42i—C41—H41E | 50.8 (7) | C8—C81—H81E | 118 (3) |
C4—C41—H41E | 114.0 (7) | H81A—C81—H81E | 53 (3) |
C41i—C41—H41E | 143.0 (6) | H81C—C81—H81E | 52 (3) |
H41A—C41—H41E | 56.0 (6) | H81D—C81—H81E | 107 (6) |
H41B—C41—H41E | 135.7 (9) | C10—C9—C8 | 124.7 (3) |
H41C—C41—H41E | 57.4 (4) | C10—C9—O1 | 122.2 (3) |
H41D—C41—H41E | 109.7 (6) | C8—C9—O1 | 113.0 (3) |
C42i—C41—H41F | 110.0 (11) | C9—C10—C5 | 116.9 (3) |
C4—C41—H41F | 109.8 (5) | C9—C10—C4 | 117.2 (3) |
C41i—C41—H41F | 110.8 (6) | C5—C10—C4 | 126.0 (3) |
| | | |
C9—O1—C2—O2 | 180.0 | C10—C4—C42—C3i | −97.1 (4) |
C9—O1—C2—C3 | 31.0 (3) | C3—C4—C42—C3i | 20.6 (5) |
C9—O1—C2—C3i | −31.0 (3) | C41—C4—C42—C3i | 133.8 (5) |
O2—C2—C3—C3i | 109.5 (3) | C41i—C4—C42—C3i | 160.9 (8) |
O1—C2—C3—C3i | −101.6 (2) | C10—C5—C6—O6 | 180.0 |
O2—C2—C3—C42i | −163.6 (17) | C51—C5—C6—O6 | 0.0 |
O1—C2—C3—C42i | −14.7 (19) | C10—C5—C6—C7 | 0.0 |
C3i—C2—C3—C42i | 87.0 (19) | C51—C5—C6—C7 | 180.0 |
O2—C2—C3—C4 | 150.3 (3) | O6—C6—C7—C8 | 180.0 |
O1—C2—C3—C4 | −60.8 (4) | C5—C6—C7—C8 | 0.0 |
C3i—C2—C3—C4 | 40.8 (4) | O6—C6—C7—C71 | 0.0 |
C3i—C3—C4—C42i | −156.9 (4) | C5—C6—C7—C71 | 180.0 |
C2—C3—C4—C42i | 162.7 (6) | C6—C7—C8—C9 | 0.0 |
C3i—C3—C4—C42 | −21.1 (4) | C71—C7—C8—C9 | 180.0 |
C42i—C3—C4—C42 | 135.8 (8) | C6—C7—C8—C81 | 180.0 |
C2—C3—C4—C42 | −61.6 (6) | C71—C7—C8—C81 | 0.0 |
C3i—C3—C4—C10 | 98.9 (2) | C7—C8—C9—C10 | 0.0 |
C42i—C3—C4—C10 | −104.2 (4) | C81—C8—C9—C10 | 180.0 |
C2—C3—C4—C10 | 58.5 (4) | C7—C8—C9—O1 | 180.0 |
C42i—C3—C4—C3i | 156.9 (4) | C81—C8—C9—O1 | 0.0 |
C2—C3—C4—C3i | −40.4 (4) | C2—O1—C9—C10 | 0.0 |
C3i—C3—C4—C41 | −143.8 (4) | C2—O1—C9—C8 | 180.0 |
C42i—C3—C4—C41 | 13.1 (6) | C8—C9—C10—C5 | 0.0 |
C2—C3—C4—C41 | 175.8 (5) | O1—C9—C10—C5 | 180.0 |
C3i—C3—C4—C41i | −63.0 (7) | C8—C9—C10—C4 | 180.0 |
C42i—C3—C4—C41i | 93.9 (9) | O1—C9—C10—C4 | 0.0 |
C2—C3—C4—C41i | −103.5 (8) | C6—C5—C10—C9 | 0.0 |
C42—C4—C41—C42i | −136.3 (10) | C51—C5—C10—C9 | 180.0 |
C10—C4—C41—C42i | 95.8 (6) | C6—C5—C10—C4 | 180.0 |
C3i—C4—C41—C42i | −65.4 (10) | C51—C5—C10—C4 | 0.000 (1) |
C3—C4—C41—C42i | −16.5 (7) | C42i—C4—C10—C9 | −91.5 (5) |
C41i—C4—C41—C42i | −155.0 (6) | C42—C4—C10—C9 | 91.5 (5) |
C42i—C4—C41—C41i | 155.0 (6) | C3i—C4—C10—C9 | 29.5 (3) |
C42—C4—C41—C41i | 18.7 (5) | C3—C4—C10—C9 | −29.5 (3) |
C10—C4—C41—C41i | −109.2 (4) | C41—C4—C10—C9 | −137.9 (4) |
C3i—C4—C41—C41i | 89.5 (7) | C41i—C4—C10—C9 | 137.9 (4) |
C3—C4—C41—C41i | 138.5 (4) | C42i—C4—C10—C5 | 88.5 (5) |
C42i—C4—C42—C41i | −73.7 (15) | C42—C4—C10—C5 | −88.5 (5) |
C10—C4—C42—C41i | 102.0 (7) | C3i—C4—C10—C5 | −150.5 (3) |
C3i—C4—C42—C41i | −160.9 (8) | C3—C4—C10—C5 | 150.5 (3) |
C3—C4—C42—C41i | −140.3 (6) | C41—C4—C10—C5 | 42.1 (4) |
C41—C4—C42—C41i | −27.1 (7) | C41i—C4—C10—C5 | −42.1 (4) |
C42i—C4—C42—C3i | 87.2 (13) | | |
Symmetry code: (i) x, −y+1/2, z. |
(cum110c) 6-hydroxy-4,4,5,7,8-pentamethyl
o-3,4-dihydrocoumarin
top
Crystal data top
C14H18O3 | V = 1248.7 (6) Å3 |
Mr = 234.28 | Z = 4 |
P21/n, monoclinic | F(000) = 504 |
a = 13.449 (4) Å | Dx = 1.246 Mg m−3 |
b = 6.757 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 13.746 (4) Å | µ = 0.09 mm−1 |
α = 90° | T = 110 K |
β = 91.54 (2)° | , colourlees |
γ = 90° | 0.35 × 0.25 × 0.12 mm |
Data collection top
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 29.6°, θmin = 2.1° |
8052 measured reflections | h = −18→17 |
3237 independent reflections | k = −9→5 |
1764 reflections with I > 2σ(I) | l = −18→18 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.069 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.205 | w = 1/[σ2(Fo2) + (0.0909P)2 + 0.920P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.438 |
3237 reflections | Δρmax = 0.34 e Å−3 |
227 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0014 (17) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.79680 (13) | 0.2079 (3) | −0.30433 (13) | 0.0209 (4) | |
O6 | 1.15842 (13) | 0.2488 (3) | −0.48101 (14) | 0.0218 (4) | |
H6 | 1.161 (3) | 0.259 (5) | −0.548 (3) | 0.050 (11)* | |
O2 | 0.70025 (14) | 0.2076 (3) | −0.17918 (14) | 0.0305 (5) | |
C2 | 0.78184 (19) | 0.2434 (4) | −0.20983 (19) | 0.0220 (6) | |
C3 | 0.8679 (2) | 0.3273 (5) | −0.1533 (2) | 0.0246 (6) | |
H3A | 0.853 (2) | 0.313 (5) | −0.084 (3) | 0.039 (9)* | |
H3B | 0.873 (2) | 0.471 (5) | −0.174 (2) | 0.035 (9)* | |
C4 | 0.96643 (19) | 0.2220 (4) | −0.17629 (18) | 0.0205 (6) | |
C41 | 1.0462 (2) | 0.3314 (5) | −0.1150 (2) | 0.0297 (7) | |
H41A | 1.019 (3) | 0.347 (5) | −0.048 (3) | 0.048 (10)* | |
H41B | 1.056 (2) | 0.467 (6) | −0.142 (3) | 0.045 (10)* | |
H41C | 1.109 (3) | 0.260 (5) | −0.109 (3) | 0.042 (10)* | |
C42 | 0.9609 (3) | 0.0038 (5) | −0.1448 (2) | 0.0294 (7) | |
H42A | 0.943 (2) | −0.007 (5) | −0.075 (3) | 0.034 (9)* | |
H42B | 1.026 (2) | −0.059 (5) | −0.154 (2) | 0.034 (9)* | |
H42C | 0.905 (3) | −0.072 (5) | −0.182 (3) | 0.041 (9)* | |
C5 | 1.06907 (18) | 0.2305 (4) | −0.33569 (18) | 0.0176 (5) | |
C51 | 1.1700 (2) | 0.2060 (5) | −0.2854 (2) | 0.0259 (6) | |
H51A | 1.220 (2) | 0.154 (5) | −0.330 (2) | 0.031 (9)* | |
H51B | 1.165 (2) | 0.102 (4) | −0.228 (2) | 0.024 (8)* | |
H51C | 1.194 (3) | 0.339 (5) | −0.257 (3) | 0.051 (10)* | |
C6 | 1.06783 (17) | 0.2440 (4) | −0.43768 (19) | 0.0176 (5) | |
C7 | 0.97903 (18) | 0.2523 (4) | −0.49408 (18) | 0.0169 (5) | |
C71 | 0.9845 (2) | 0.2615 (4) | −0.60336 (19) | 0.0209 (6) | |
H71A | 1.024 (2) | 0.145 (5) | −0.629 (2) | 0.030 (9)* | |
H71B | 1.022 (3) | 0.379 (5) | −0.629 (2) | 0.045 (10)* | |
H71C | 0.919 (3) | 0.256 (5) | −0.634 (2) | 0.033 (9)* | |
C8 | 0.88875 (18) | 0.2462 (4) | −0.44611 (18) | 0.0175 (5) | |
C81 | 0.7903 (2) | 0.2519 (4) | −0.5014 (2) | 0.0228 (6) | |
H81A | 0.783 (3) | 0.363 (6) | −0.544 (3) | 0.058 (11)* | |
H81B | 0.733 (3) | 0.269 (5) | −0.455 (3) | 0.038 (9)* | |
H81C | 0.775 (3) | 0.134 (5) | −0.537 (3) | 0.049 (10)* | |
C9 | 0.89105 (18) | 0.2349 (4) | −0.34514 (18) | 0.0169 (5) | |
C10 | 0.97875 (18) | 0.2318 (4) | −0.28730 (18) | 0.0177 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0153 (9) | 0.0307 (11) | 0.0168 (9) | −0.0024 (7) | 0.0015 (7) | −0.0011 (8) |
O6 | 0.0148 (9) | 0.0287 (10) | 0.0223 (10) | −0.0003 (7) | 0.0065 (7) | 0.0003 (8) |
O2 | 0.0225 (10) | 0.0438 (13) | 0.0255 (10) | −0.0021 (9) | 0.0076 (8) | −0.0006 (9) |
C2 | 0.0218 (13) | 0.0246 (14) | 0.0199 (12) | 0.0027 (11) | 0.0063 (10) | 0.0016 (10) |
C3 | 0.0232 (14) | 0.0322 (16) | 0.0186 (13) | 0.0011 (12) | 0.0029 (11) | −0.0023 (12) |
C4 | 0.0186 (12) | 0.0271 (14) | 0.0160 (12) | 0.0007 (10) | 0.0010 (9) | −0.0010 (10) |
C41 | 0.0260 (16) | 0.0407 (18) | 0.0223 (15) | −0.0019 (13) | −0.0039 (12) | −0.0064 (13) |
C42 | 0.0296 (17) | 0.0344 (17) | 0.0243 (15) | 0.0004 (13) | 0.0016 (13) | 0.0045 (12) |
C5 | 0.0143 (11) | 0.0188 (12) | 0.0196 (12) | −0.0004 (9) | −0.0006 (9) | 0.0002 (10) |
C51 | 0.0184 (13) | 0.0351 (17) | 0.0241 (14) | 0.0019 (12) | 0.0006 (11) | −0.0011 (12) |
C6 | 0.0145 (11) | 0.0155 (12) | 0.0231 (13) | −0.0002 (9) | 0.0035 (10) | −0.0018 (10) |
C7 | 0.0197 (12) | 0.0147 (11) | 0.0165 (12) | −0.0006 (10) | 0.0007 (9) | −0.0008 (9) |
C71 | 0.0209 (13) | 0.0229 (14) | 0.0190 (12) | 0.0000 (11) | 0.0029 (10) | −0.0009 (11) |
C8 | 0.0188 (12) | 0.0159 (12) | 0.0178 (12) | −0.0003 (10) | −0.0001 (9) | −0.0006 (10) |
C81 | 0.0213 (13) | 0.0278 (15) | 0.0191 (13) | 0.0015 (11) | −0.0010 (10) | −0.0005 (12) |
C9 | 0.0144 (11) | 0.0178 (12) | 0.0186 (12) | −0.0020 (9) | 0.0028 (9) | −0.0003 (10) |
C10 | 0.0167 (12) | 0.0190 (13) | 0.0173 (12) | 0.0009 (10) | −0.0007 (9) | −0.0002 (10) |
Geometric parameters (Å, º) top
O1—C2 | 1.341 (3) | C5—C10 | 1.401 (4) |
O1—C9 | 1.412 (3) | C5—C6 | 1.405 (3) |
O6—C6 | 1.371 (3) | C5—C51 | 1.515 (4) |
O2—C2 | 1.210 (3) | C6—C7 | 1.407 (3) |
C2—C3 | 1.489 (4) | C7—C8 | 1.398 (4) |
C3—C4 | 1.544 (4) | C7—C71 | 1.507 (3) |
C4—C41 | 1.536 (4) | C8—C9 | 1.390 (3) |
C4—C42 | 1.539 (4) | C8—C81 | 1.508 (4) |
C4—C10 | 1.541 (4) | C9—C10 | 1.405 (3) |
| | | |
C2—O1—C9 | 121.43 (19) | O6—C6—C7 | 120.7 (2) |
O2—C2—O1 | 117.5 (2) | C5—C6—C7 | 122.7 (2) |
O2—C2—C3 | 126.4 (2) | C8—C7—C6 | 118.3 (2) |
O1—C2—C3 | 116.0 (2) | C8—C7—C71 | 122.5 (2) |
C2—C3—C4 | 112.1 (2) | C6—C7—C71 | 119.2 (2) |
C41—C4—C42 | 110.2 (2) | C9—C8—C7 | 118.5 (2) |
C41—C4—C10 | 115.5 (2) | C9—C8—C81 | 120.0 (2) |
C42—C4—C10 | 109.1 (2) | C7—C8—C81 | 121.6 (2) |
C41—C4—C3 | 104.9 (2) | C8—C9—C10 | 124.2 (2) |
C42—C4—C3 | 109.6 (2) | C8—C9—O1 | 114.1 (2) |
C10—C4—C3 | 107.4 (2) | C10—C9—O1 | 121.5 (2) |
C10—C5—C6 | 119.1 (2) | C5—C10—C9 | 117.2 (2) |
C10—C5—C51 | 124.2 (2) | C5—C10—C4 | 126.0 (2) |
C6—C5—C51 | 116.6 (2) | C9—C10—C4 | 116.8 (2) |
O6—C6—C5 | 116.6 (2) | | |
| | | |
C9—O1—C2—O2 | −176.4 (2) | C81—C8—C9—C10 | −179.0 (2) |
C9—O1—C2—C3 | 4.7 (3) | C7—C8—C9—O1 | −173.5 (2) |
O2—C2—C3—C4 | 137.2 (3) | C81—C8—C9—O1 | 6.6 (3) |
O1—C2—C3—C4 | −44.1 (3) | C2—O1—C9—C8 | −163.0 (2) |
C2—C3—C4—C41 | 178.1 (2) | C2—O1—C9—C10 | 22.4 (3) |
C2—C3—C4—C42 | −63.7 (3) | C6—C5—C10—C9 | 3.7 (4) |
C2—C3—C4—C10 | 54.7 (3) | C51—C5—C10—C9 | −173.4 (2) |
C10—C5—C6—O6 | 177.8 (2) | C6—C5—C10—C4 | −178.9 (2) |
C51—C5—C6—O6 | −4.8 (3) | C51—C5—C10—C4 | 4.0 (4) |
C10—C5—C6—C7 | −2.1 (4) | C8—C9—C10—C5 | −3.2 (4) |
C51—C5—C6—C7 | 175.2 (2) | O1—C9—C10—C5 | 170.8 (2) |
O6—C6—C7—C8 | 179.8 (2) | C8—C9—C10—C4 | 179.1 (2) |
C5—C6—C7—C8 | −0.2 (4) | O1—C9—C10—C4 | −6.9 (3) |
O6—C6—C7—C71 | 1.5 (4) | C41—C4—C10—C5 | 35.9 (4) |
C5—C6—C7—C71 | −178.5 (2) | C42—C4—C10—C5 | −88.8 (3) |
C6—C7—C8—C9 | 0.8 (3) | C3—C4—C10—C5 | 152.5 (3) |
C71—C7—C8—C9 | 179.0 (2) | C41—C4—C10—C9 | −146.7 (3) |
C6—C7—C8—C81 | −179.3 (2) | C42—C4—C10—C9 | 88.6 (3) |
C71—C7—C8—C81 | −1.1 (4) | C3—C4—C10—C9 | −30.1 (3) |
C7—C8—C9—C10 | 0.9 (4) | | |
(cum150c) 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin
top
Crystal data top
C14H18O3 | V = 1256.0 (6) Å3 |
Mr = 234.28 | Z = 4 |
P21/n, monoclinic | F(000) = 504 |
a = 13.429 (4) Å | Dx = 1.239 Mg m−3 |
b = 6.784 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 13.792 (4) Å | µ = 0.09 mm−1 |
α = 90° | T = 150 K |
β = 91.54 (2)° | , colourlees |
γ = 90° | 0.35 × 0.25 × 0.12 mm |
Data collection top
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 30.2°, θmin = 3.0° |
10354 measured reflections | h = −18→18 |
3323 independent reflections | k = −9→5 |
2085 reflections with I > 2σ(I) | l = −18→19 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.152 | w = 1/[σ2(Fo2) + (0.0727P)2 + 0.350P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.010 |
3323 reflections | Δρmax = 0.34 e Å−3 |
227 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0007 (13) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.79717 (9) | 0.20793 (19) | −0.30444 (8) | 0.0239 (3) | |
O6 | 1.15870 (9) | 0.24886 (19) | −0.48134 (10) | 0.0260 (3) | |
H6 | 1.1537 (19) | 0.262 (3) | −0.542 (2) | 0.049 (8)* | |
O2 | 0.70072 (10) | 0.2078 (2) | −0.17939 (10) | 0.0363 (4) | |
C2 | 0.78223 (14) | 0.2439 (3) | −0.20981 (13) | 0.0257 (4) | |
C3 | 0.86865 (14) | 0.3271 (3) | −0.15457 (13) | 0.0286 (4) | |
H3A | 0.8527 (16) | 0.317 (3) | −0.0854 (16) | 0.034 (6)* | |
H3B | 0.8710 (15) | 0.470 (3) | −0.1747 (14) | 0.033 (6)* | |
C4 | 0.96725 (13) | 0.2227 (3) | −0.17730 (12) | 0.0243 (4) | |
C41 | 1.04704 (17) | 0.3337 (4) | −0.11738 (16) | 0.0379 (5) | |
H41A | 1.0226 (18) | 0.351 (3) | −0.0525 (18) | 0.047 (6)* | |
H41B | 1.0586 (18) | 0.463 (4) | −0.1457 (17) | 0.048 (7)* | |
H41C | 1.115 (2) | 0.262 (3) | −0.1131 (18) | 0.049 (7)* | |
C42 | 0.96290 (19) | 0.0062 (3) | −0.14531 (16) | 0.0350 (5) | |
H42A | 0.9492 (17) | −0.002 (3) | −0.0779 (17) | 0.045 (6)* | |
H42B | 1.0287 (17) | −0.066 (3) | −0.1580 (15) | 0.040 (6)* | |
H42C | 0.9098 (17) | −0.067 (3) | −0.1820 (16) | 0.036 (6)* | |
C5 | 1.06963 (12) | 0.2313 (2) | −0.33677 (12) | 0.0201 (4) | |
C51 | 1.17061 (14) | 0.2077 (4) | −0.28716 (15) | 0.0303 (5) | |
H51A | 1.2193 (18) | 0.149 (3) | −0.3327 (17) | 0.046 (6)* | |
H51B | 1.1706 (16) | 0.106 (3) | −0.2344 (16) | 0.035 (6)* | |
H51C | 1.197 (2) | 0.336 (4) | −0.2593 (18) | 0.058 (7)* | |
C6 | 1.06766 (12) | 0.2447 (2) | −0.43843 (12) | 0.0192 (4) | |
C7 | 0.97892 (12) | 0.2527 (2) | −0.49386 (12) | 0.0186 (4) | |
C71 | 0.98361 (15) | 0.2614 (3) | −0.60288 (13) | 0.0241 (4) | |
H71A | 1.0195 (16) | 0.147 (3) | −0.6283 (15) | 0.039 (6)* | |
H71B | 1.0187 (18) | 0.379 (4) | −0.6260 (16) | 0.051 (7)* | |
H71C | 0.918 (2) | 0.263 (3) | −0.6337 (18) | 0.051 (7)* | |
C8 | 0.88857 (12) | 0.2457 (2) | −0.44630 (12) | 0.0186 (4) | |
C81 | 0.78991 (14) | 0.2511 (3) | −0.50047 (14) | 0.0253 (4) | |
H81A | 0.786 (2) | 0.355 (4) | −0.549 (2) | 0.063 (8)* | |
H81B | 0.734 (2) | 0.262 (4) | −0.459 (2) | 0.066 (8)* | |
H81C | 0.778 (2) | 0.134 (4) | −0.5394 (19) | 0.064 (8)* | |
C9 | 0.89165 (12) | 0.2346 (2) | −0.34520 (12) | 0.0182 (4) | |
C10 | 0.97912 (12) | 0.2320 (2) | −0.28794 (12) | 0.0189 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0178 (6) | 0.0354 (8) | 0.0188 (6) | −0.0021 (5) | 0.0046 (5) | −0.0003 (5) |
O6 | 0.0176 (6) | 0.0339 (8) | 0.0268 (7) | 0.0005 (5) | 0.0063 (5) | 0.0010 (6) |
O2 | 0.0254 (7) | 0.0549 (10) | 0.0293 (7) | −0.0031 (7) | 0.0124 (6) | −0.0024 (7) |
C2 | 0.0256 (9) | 0.0303 (10) | 0.0215 (8) | 0.0043 (8) | 0.0072 (7) | 0.0019 (7) |
C3 | 0.0282 (10) | 0.0380 (12) | 0.0199 (9) | 0.0031 (9) | 0.0042 (7) | −0.0052 (8) |
C4 | 0.0220 (8) | 0.0339 (10) | 0.0168 (8) | 0.0009 (8) | −0.0001 (6) | −0.0007 (7) |
C41 | 0.0316 (11) | 0.0561 (16) | 0.0258 (10) | −0.0008 (11) | −0.0044 (8) | −0.0128 (10) |
C42 | 0.0401 (13) | 0.0409 (13) | 0.0241 (10) | 0.0041 (10) | 0.0020 (9) | 0.0080 (9) |
C5 | 0.0183 (8) | 0.0187 (9) | 0.0232 (8) | −0.0001 (7) | 0.0002 (6) | 0.0003 (6) |
C51 | 0.0197 (9) | 0.0419 (13) | 0.0293 (10) | 0.0043 (8) | −0.0024 (8) | −0.0010 (9) |
C6 | 0.0154 (7) | 0.0187 (9) | 0.0239 (8) | −0.0007 (6) | 0.0059 (6) | −0.0008 (7) |
C7 | 0.0217 (8) | 0.0165 (8) | 0.0177 (8) | −0.0001 (7) | 0.0032 (6) | 0.0001 (6) |
C71 | 0.0273 (9) | 0.0261 (10) | 0.0191 (8) | −0.0008 (8) | 0.0064 (7) | −0.0007 (7) |
C8 | 0.0186 (8) | 0.0179 (9) | 0.0194 (8) | 0.0002 (6) | 0.0010 (6) | −0.0006 (6) |
C81 | 0.0200 (8) | 0.0352 (11) | 0.0206 (8) | −0.0003 (8) | −0.0013 (7) | −0.0005 (8) |
C9 | 0.0165 (7) | 0.0182 (8) | 0.0201 (8) | −0.0012 (6) | 0.0054 (6) | −0.0008 (6) |
C10 | 0.0190 (8) | 0.0203 (9) | 0.0174 (7) | 0.0002 (7) | 0.0006 (6) | −0.0003 (6) |
Geometric parameters (Å, º) top
O1—C2 | 1.348 (2) | C5—C6 | 1.405 (2) |
O1—C9 | 1.4131 (19) | C5—C10 | 1.405 (2) |
O6—C6 | 1.3727 (19) | C5—C51 | 1.511 (2) |
O2—C2 | 1.208 (2) | C6—C7 | 1.400 (2) |
C2—C3 | 1.483 (3) | C7—C8 | 1.396 (2) |
C3—C4 | 1.541 (3) | C7—C71 | 1.508 (2) |
C4—C41 | 1.533 (3) | C8—C9 | 1.396 (2) |
C4—C42 | 1.535 (3) | C8—C81 | 1.504 (2) |
C4—C10 | 1.540 (2) | C9—C10 | 1.398 (2) |
| | | |
C2—O1—C9 | 121.37 (13) | O6—C6—C5 | 116.02 (15) |
O2—C2—O1 | 117.36 (17) | C7—C6—C5 | 122.73 (14) |
O2—C2—C3 | 127.07 (16) | C8—C7—C6 | 118.70 (15) |
O1—C2—C3 | 115.56 (15) | C8—C7—C71 | 122.02 (16) |
C2—C3—C4 | 112.67 (16) | C6—C7—C71 | 119.24 (15) |
C41—C4—C42 | 110.27 (18) | C7—C8—C9 | 117.94 (15) |
C41—C4—C10 | 115.13 (16) | C7—C8—C81 | 122.08 (15) |
C42—C4—C10 | 109.25 (15) | C9—C8—C81 | 119.98 (15) |
C41—C4—C3 | 104.86 (16) | C8—C9—C10 | 124.53 (14) |
C42—C4—C3 | 109.97 (16) | C8—C9—O1 | 113.67 (14) |
C10—C4—C3 | 107.17 (14) | C10—C9—O1 | 121.57 (14) |
C6—C5—C10 | 119.01 (15) | C9—C10—C5 | 116.99 (15) |
C6—C5—C51 | 116.84 (15) | C9—C10—C4 | 116.91 (14) |
C10—C5—C51 | 124.10 (16) | C5—C10—C4 | 126.06 (15) |
O6—C6—C7 | 121.25 (15) | | |
| | | |
C9—O1—C2—O2 | −176.27 (16) | C81—C8—C9—C10 | −178.95 (17) |
C9—O1—C2—C3 | 4.6 (2) | C7—C8—C9—O1 | −173.86 (15) |
O2—C2—C3—C4 | 136.8 (2) | C81—C8—C9—O1 | 6.5 (2) |
O1—C2—C3—C4 | −44.1 (2) | C2—O1—C9—C8 | −162.86 (16) |
C2—C3—C4—C41 | 177.71 (17) | C2—O1—C9—C10 | 22.4 (2) |
C2—C3—C4—C42 | −63.7 (2) | C8—C9—C10—C5 | −3.1 (3) |
C2—C3—C4—C10 | 54.9 (2) | O1—C9—C10—C5 | 171.06 (15) |
C10—C5—C6—O6 | 178.22 (16) | C8—C9—C10—C4 | 179.02 (15) |
C51—C5—C6—O6 | −4.5 (2) | O1—C9—C10—C4 | −6.9 (2) |
C10—C5—C6—C7 | −2.0 (3) | C6—C5—C10—C9 | 3.6 (2) |
C51—C5—C6—C7 | 175.32 (17) | C51—C5—C10—C9 | −173.51 (17) |
O6—C6—C7—C8 | 179.31 (16) | C6—C5—C10—C4 | −178.71 (16) |
C5—C6—C7—C8 | −0.5 (2) | C51—C5—C10—C4 | 4.2 (3) |
O6—C6—C7—C71 | 1.4 (2) | C41—C4—C10—C9 | −146.16 (18) |
C5—C6—C7—C71 | −178.39 (16) | C42—C4—C10—C9 | 89.2 (2) |
C6—C7—C8—C9 | 1.1 (2) | C3—C4—C10—C9 | −30.0 (2) |
C71—C7—C8—C9 | 178.99 (16) | C41—C4—C10—C5 | 36.1 (3) |
C6—C7—C8—C81 | −179.25 (17) | C42—C4—C10—C5 | −88.6 (2) |
C71—C7—C8—C81 | −1.4 (3) | C3—C4—C10—C5 | 152.33 (18) |
C7—C8—C9—C10 | 0.7 (3) | | |
(cum220) 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin
top
Crystal data top
C14H18O3 | V = 1277.6 (4) Å3 |
Mr = 234.28 | Z = 4 |
P21/n, monoclinic | F(000) = 504 |
a = 13.345 (2) Å | Dx = 1.218 Mg m−3 |
b = 6.853 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 13.973 (3) Å | µ = 0.08 mm−1 |
α = 90° | T = 220 K |
β = 91.25 (2)° | , colourlees |
γ = 90° | 0.44 × 0.38 × 0.19 mm |
Data collection top
Radiation source: fine-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 29.4°, θmin = 3.3° |
5221 measured reflections | h = −12→17 |
2975 independent reflections | k = −9→9 |
1955 reflections with I > 2σ(I) | l = −18→15 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.171 | w = 1/[σ2(Fo2) + (0.078P)2 + 0.099P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.340 |
2975 reflections | Δρmax = 0.38 e Å−3 |
227 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0000 (19) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.79818 (7) | 0.21076 (17) | −0.30423 (8) | 0.0369 (3) | |
O6 | 1.15996 (8) | 0.24937 (16) | −0.48359 (11) | 0.0404 (3) | |
H6 | 1.1576 (18) | 0.261 (3) | −0.544 (2) | 0.064 (7)* | |
O2 | 0.70200 (9) | 0.2102 (2) | −0.18045 (10) | 0.0594 (4) | |
C2 | 0.78373 (12) | 0.2462 (2) | −0.21098 (13) | 0.0409 (4) | |
C3 | 0.87049 (13) | 0.3313 (3) | −0.15758 (14) | 0.0476 (5) | |
H3A | 0.8550 (16) | 0.319 (3) | −0.0897 (19) | 0.069 (6)* | |
H3B | 0.8739 (13) | 0.470 (3) | −0.1760 (14) | 0.054 (5)* | |
C4 | 0.97048 (12) | 0.2307 (2) | −0.18089 (13) | 0.0395 (4) | |
C41 | 1.04961 (17) | 0.3449 (5) | −0.12368 (18) | 0.0684 (7) | |
H41A | 1.0207 (19) | 0.367 (4) | −0.062 (2) | 0.091 (8)* | |
H41B | 1.0631 (13) | 0.476 (3) | −0.1514 (14) | 0.049 (6)* | |
H41C | 1.112 (2) | 0.275 (4) | −0.121 (2) | 0.086 (8)* | |
C42 | 0.96690 (19) | 0.0159 (4) | −0.14754 (16) | 0.0619 (6) | |
H42A | 0.9535 (16) | 0.004 (4) | −0.0789 (17) | 0.076 (7)* | |
H42B | 1.0344 (19) | −0.042 (4) | −0.1539 (17) | 0.082 (7)* | |
H42C | 0.9081 (18) | −0.065 (3) | −0.1886 (17) | 0.077 (7)* | |
C5 | 1.07157 (10) | 0.23537 (19) | −0.33974 (12) | 0.0301 (3) | |
C51 | 1.17397 (12) | 0.2134 (3) | −0.29145 (16) | 0.0484 (5) | |
H51A | 1.2189 (18) | 0.159 (3) | −0.3373 (17) | 0.072 (6)* | |
H51B | 1.1718 (16) | 0.117 (3) | −0.2386 (17) | 0.069 (7)* | |
H51C | 1.1992 (17) | 0.332 (4) | −0.2655 (17) | 0.068 (6)* | |
C6 | 1.06879 (10) | 0.24643 (18) | −0.43978 (12) | 0.0296 (3) | |
C7 | 0.97893 (10) | 0.25250 (17) | −0.49408 (11) | 0.0278 (3) | |
C71 | 0.98267 (14) | 0.2598 (2) | −0.60150 (12) | 0.0363 (4) | |
H71A | 1.0206 (14) | 0.153 (3) | −0.6234 (14) | 0.058 (6)* | |
H71B | 1.0177 (14) | 0.377 (3) | −0.6193 (14) | 0.060 (6)* | |
H71C | 0.918 (2) | 0.259 (3) | −0.6340 (19) | 0.074 (8)* | |
C8 | 0.88888 (10) | 0.24588 (18) | −0.44551 (11) | 0.0278 (3) | |
C81 | 0.78870 (12) | 0.2494 (3) | −0.49783 (14) | 0.0389 (4) | |
H81A | 0.7822 (17) | 0.352 (4) | −0.5422 (18) | 0.074 (7)* | |
H81B | 0.738 (2) | 0.267 (4) | −0.449 (2) | 0.104 (10)* | |
H81C | 0.7775 (17) | 0.138 (4) | −0.5313 (18) | 0.075 (7)* | |
C9 | 0.89247 (10) | 0.23684 (19) | −0.34580 (11) | 0.0280 (3) | |
C10 | 0.98119 (10) | 0.23652 (19) | −0.29019 (11) | 0.0295 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0274 (5) | 0.0535 (7) | 0.0302 (7) | −0.0024 (4) | 0.0078 (4) | −0.0012 (5) |
O6 | 0.0288 (5) | 0.0498 (7) | 0.0433 (8) | 0.0006 (4) | 0.0123 (5) | 0.0008 (5) |
O2 | 0.0458 (7) | 0.0868 (10) | 0.0465 (9) | −0.0074 (6) | 0.0218 (6) | −0.0039 (7) |
C2 | 0.0390 (8) | 0.0510 (10) | 0.0333 (10) | 0.0041 (6) | 0.0133 (7) | 0.0001 (6) |
C3 | 0.0468 (9) | 0.0613 (12) | 0.0350 (11) | 0.0063 (8) | 0.0072 (7) | −0.0103 (8) |
C4 | 0.0383 (8) | 0.0541 (10) | 0.0261 (9) | 0.0055 (6) | 0.0005 (6) | −0.0049 (6) |
C41 | 0.0525 (11) | 0.105 (2) | 0.0474 (14) | 0.0030 (12) | −0.0076 (10) | −0.0313 (13) |
C42 | 0.0741 (14) | 0.0722 (14) | 0.0395 (12) | 0.0161 (11) | 0.0059 (10) | 0.0180 (10) |
C5 | 0.0266 (6) | 0.0307 (7) | 0.0329 (9) | 0.0019 (5) | −0.0009 (6) | −0.0033 (5) |
C51 | 0.0309 (8) | 0.0628 (12) | 0.0514 (13) | 0.0059 (7) | −0.0051 (8) | −0.0065 (9) |
C6 | 0.0268 (6) | 0.0269 (7) | 0.0353 (9) | −0.0003 (5) | 0.0082 (6) | −0.0015 (5) |
C7 | 0.0328 (7) | 0.0247 (6) | 0.0260 (8) | 0.0002 (5) | 0.0047 (6) | −0.0003 (5) |
C71 | 0.0449 (9) | 0.0371 (9) | 0.0271 (9) | 0.0001 (6) | 0.0084 (7) | −0.0012 (6) |
C8 | 0.0280 (6) | 0.0286 (7) | 0.0269 (8) | −0.0014 (5) | 0.0007 (6) | −0.0010 (5) |
C81 | 0.0306 (7) | 0.0507 (10) | 0.0353 (10) | 0.0009 (6) | −0.0016 (7) | 0.0004 (7) |
C9 | 0.0254 (6) | 0.0305 (7) | 0.0283 (8) | −0.0001 (5) | 0.0062 (5) | −0.0005 (5) |
C10 | 0.0315 (7) | 0.0312 (7) | 0.0258 (8) | 0.0013 (5) | −0.0002 (6) | −0.0020 (5) |
Geometric parameters (Å, º) top
O1—C2 | 1.343 (2) | C5—C6 | 1.400 (2) |
O1—C9 | 1.4088 (16) | C5—C10 | 1.404 (2) |
O6—C6 | 1.3740 (17) | C5—C51 | 1.518 (2) |
O2—C2 | 1.205 (2) | C6—C7 | 1.406 (2) |
C2—C3 | 1.483 (3) | C7—C8 | 1.3936 (19) |
C3—C4 | 1.543 (2) | C7—C71 | 1.504 (2) |
C4—C41 | 1.527 (3) | C8—C9 | 1.394 (2) |
C4—C10 | 1.538 (2) | C8—C81 | 1.510 (2) |
C4—C42 | 1.544 (3) | C9—C10 | 1.402 (2) |
| | | |
C2—O1—C9 | 121.69 (13) | O6—C6—C7 | 120.83 (15) |
O2—C2—O1 | 117.16 (17) | C5—C6—C7 | 122.99 (13) |
O2—C2—C3 | 127.22 (17) | C8—C7—C6 | 118.08 (14) |
O1—C2—C3 | 115.60 (14) | C8—C7—C71 | 122.34 (14) |
C2—C3—C4 | 112.77 (14) | C6—C7—C71 | 119.56 (13) |
C41—C4—C10 | 115.37 (16) | C7—C8—C9 | 118.48 (13) |
C41—C4—C3 | 104.58 (15) | C7—C8—C81 | 121.84 (15) |
C10—C4—C3 | 107.30 (14) | C9—C8—C81 | 119.68 (13) |
C41—C4—C42 | 110.87 (19) | C8—C9—C10 | 124.34 (13) |
C10—C4—C42 | 109.19 (14) | C8—C9—O1 | 113.96 (12) |
C3—C4—C42 | 109.25 (16) | C10—C9—O1 | 121.49 (14) |
C6—C5—C10 | 119.21 (13) | C9—C10—C5 | 116.80 (15) |
C6—C5—C51 | 116.95 (14) | C9—C10—C4 | 117.06 (13) |
C10—C5—C51 | 123.78 (16) | C5—C10—C4 | 126.10 (14) |
O6—C6—C5 | 116.18 (14) | | |
| | | |
C9—O1—C2—O2 | −176.22 (14) | C81—C8—C9—C10 | −178.76 (13) |
C9—O1—C2—C3 | 5.4 (2) | C7—C8—C9—O1 | −173.90 (11) |
O2—C2—C3—C4 | 137.63 (19) | C81—C8—C9—O1 | 6.46 (18) |
O1—C2—C3—C4 | −44.2 (2) | C2—O1—C9—C8 | −163.41 (13) |
C2—C3—C4—C41 | 177.12 (19) | C2—O1—C9—C10 | 21.6 (2) |
C2—C3—C4—C10 | 54.1 (2) | C8—C9—C10—C5 | −3.3 (2) |
C2—C3—C4—C42 | −64.2 (2) | O1—C9—C10—C5 | 171.07 (12) |
C10—C5—C6—O6 | 178.48 (12) | C8—C9—C10—C4 | 178.62 (12) |
C51—C5—C6—O6 | −4.21 (19) | O1—C9—C10—C4 | −6.98 (19) |
C10—C5—C6—C7 | −2.1 (2) | C6—C5—C10—C9 | 3.79 (19) |
C51—C5—C6—C7 | 175.21 (14) | C51—C5—C10—C9 | −173.32 (14) |
O6—C6—C7—C8 | 178.97 (12) | C6—C5—C10—C4 | −178.36 (12) |
C5—C6—C7—C8 | −0.42 (18) | C51—C5—C10—C4 | 4.5 (2) |
O6—C6—C7—C71 | 0.76 (18) | C41—C4—C10—C9 | −145.20 (17) |
C5—C6—C7—C71 | −178.63 (12) | C3—C4—C10—C9 | −29.13 (18) |
C6—C7—C8—C9 | 1.04 (18) | C42—C4—C10—C9 | 89.17 (17) |
C71—C7—C8—C9 | 179.19 (12) | C41—C4—C10—C5 | 37.0 (2) |
C6—C7—C8—C81 | −179.32 (13) | C3—C4—C10—C5 | 153.03 (15) |
C71—C7—C8—C81 | −1.2 (2) | C42—C4—C10—C5 | −88.67 (19) |
C7—C8—C9—C10 | 0.9 (2) | | |
(cum222) 6-hyroxy-4,4,5,7,8-pentamathyl-3,4-dihydrocoumarin
top
Crystal data top
C14H18O3 | V = 1276.9 (3) Å3 |
Mr = 234.28 | Z = 4 |
P21/n, monoclinic | F(000) = 504 |
a = 13.344 (2) Å | Dx = 1.219 Mg m−3 |
b = 6.854 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 13.964 (2) Å | µ = 0.08 mm−1 |
α = 90° | T = 220 K |
β = 91.18 (2)° | , colourlees |
γ = 90° | 0.44 × 0.38 × 0.12 mm |
Data collection top
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 29.6°, θmin = 3.3° |
5901 measured reflections | h = −16→15 |
2966 independent reflections | k = −9→9 |
1256 reflections with I > 2σ(I) | l = −18→14 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.069 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.226 | w = 1/[σ2(Fo2) + (0.1493P)2 + 0.1P] where P = (Fo2 + 2Fc2)/3 |
S = 0.83 | (Δ/σ)max = 0.099 |
2966 reflections | Δρmax = 0.50 e Å−3 |
227 parameters | Δρmin = −0.35 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.001 (2) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.79796 (13) | 0.2117 (3) | −0.30463 (11) | 0.0434 (5) | |
O6 | 1.16002 (14) | 0.2499 (2) | −0.48383 (14) | 0.0462 (5) | |
H6 | 1.161 (3) | 0.268 (6) | −0.553 (3) | 0.123 (16)* | |
O2 | 0.70231 (17) | 0.2098 (3) | −0.18039 (15) | 0.0679 (7) | |
C2 | 0.7841 (2) | 0.2472 (4) | −0.21136 (19) | 0.0472 (7) | |
C3 | 0.8710 (2) | 0.3324 (5) | −0.1580 (2) | 0.0549 (8) | |
H3A | 0.858 (2) | 0.321 (4) | −0.090 (2) | 0.069 (9)* | |
H3B | 0.8742 (19) | 0.475 (4) | −0.1779 (18) | 0.055 (8)* | |
C4 | 0.9707 (2) | 0.2317 (4) | −0.18134 (17) | 0.0460 (7) | |
C41 | 1.0503 (3) | 0.3466 (8) | −0.1242 (3) | 0.0771 (12) | |
H41A | 1.021 (3) | 0.377 (5) | −0.068 (3) | 0.095 (12)* | |
H41B | 1.062 (2) | 0.474 (4) | −0.1570 (19) | 0.052 (9)* | |
H41C | 1.113 (3) | 0.271 (5) | −0.123 (3) | 0.094 (14)* | |
C42 | 0.9678 (4) | 0.0183 (6) | −0.1468 (3) | 0.0735 (11) | |
H42A | 0.956 (2) | 0.011 (5) | −0.078 (2) | 0.090 (11)* | |
H42B | 1.038 (3) | −0.043 (5) | −0.154 (2) | 0.089 (11)* | |
H42C | 0.914 (2) | −0.067 (4) | −0.186 (2) | 0.066 (9)* | |
C5 | 1.07135 (19) | 0.2360 (3) | −0.33939 (17) | 0.0359 (6) | |
C51 | 1.1743 (2) | 0.2151 (6) | −0.2920 (2) | 0.0556 (8) | |
H51A | 1.214 (3) | 0.169 (5) | −0.340 (3) | 0.097 (12)* | |
H51B | 1.173 (2) | 0.126 (4) | −0.235 (2) | 0.067 (9)* | |
H51C | 1.197 (3) | 0.337 (5) | −0.267 (2) | 0.083 (11)* | |
C6 | 1.06876 (18) | 0.2466 (3) | −0.44038 (17) | 0.0341 (6) | |
C7 | 0.97902 (19) | 0.2520 (3) | −0.49366 (16) | 0.0323 (6) | |
C71 | 0.9827 (3) | 0.2597 (4) | −0.60184 (18) | 0.0422 (7) | |
H71A | 1.020 (2) | 0.158 (5) | −0.624 (2) | 0.066 (9)* | |
H71B | 1.017 (2) | 0.376 (4) | −0.6191 (18) | 0.058 (8)* | |
H71C | 0.910 (4) | 0.252 (5) | −0.631 (3) | 0.100 (14)* | |
C8 | 0.88896 (18) | 0.2458 (3) | −0.44596 (16) | 0.0332 (6) | |
C81 | 0.7890 (2) | 0.2493 (5) | −0.4975 (2) | 0.0455 (7) | |
H81A | 0.787 (3) | 0.347 (5) | −0.546 (2) | 0.090 (11)* | |
H81B | 0.736 (3) | 0.277 (5) | −0.455 (3) | 0.109 (14)* | |
H81C | 0.778 (3) | 0.133 (5) | −0.531 (2) | 0.090 (12)* | |
C9 | 0.89256 (18) | 0.2372 (3) | −0.34578 (16) | 0.0330 (6) | |
C10 | 0.98129 (19) | 0.2369 (3) | −0.29080 (16) | 0.0351 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0324 (11) | 0.0629 (12) | 0.0354 (9) | −0.0016 (8) | 0.0090 (7) | −0.0008 (8) |
O6 | 0.0336 (12) | 0.0552 (11) | 0.0503 (11) | 0.0026 (8) | 0.0115 (8) | 0.0005 (8) |
O2 | 0.0537 (15) | 0.0955 (17) | 0.0556 (12) | −0.0081 (12) | 0.0261 (10) | −0.0046 (10) |
C2 | 0.0428 (19) | 0.0579 (17) | 0.0416 (14) | 0.0060 (13) | 0.0186 (12) | 0.0019 (11) |
C3 | 0.053 (2) | 0.074 (2) | 0.0385 (15) | 0.0039 (16) | 0.0088 (13) | −0.0086 (15) |
C4 | 0.0424 (18) | 0.0639 (17) | 0.0316 (12) | 0.0054 (13) | 0.0016 (11) | −0.0035 (11) |
C41 | 0.065 (3) | 0.113 (4) | 0.052 (2) | 0.009 (2) | −0.0074 (17) | −0.033 (2) |
C42 | 0.091 (3) | 0.082 (2) | 0.0480 (18) | 0.018 (2) | 0.0084 (19) | 0.0160 (17) |
C5 | 0.0334 (16) | 0.0331 (12) | 0.0413 (13) | 0.0006 (10) | 0.0017 (10) | −0.0037 (9) |
C51 | 0.041 (2) | 0.073 (2) | 0.0526 (18) | 0.0060 (15) | −0.0055 (14) | −0.0060 (16) |
C6 | 0.0292 (15) | 0.0321 (12) | 0.0414 (12) | 0.0003 (10) | 0.0099 (10) | −0.0022 (9) |
C7 | 0.0365 (15) | 0.0279 (11) | 0.0328 (11) | −0.0001 (10) | 0.0049 (9) | −0.0023 (9) |
C71 | 0.049 (2) | 0.0438 (16) | 0.0342 (12) | 0.0007 (13) | 0.0129 (12) | −0.0015 (11) |
C8 | 0.0344 (15) | 0.0316 (12) | 0.0335 (12) | −0.0017 (10) | 0.0017 (9) | −0.0009 (9) |
C81 | 0.0388 (18) | 0.0575 (18) | 0.0401 (14) | −0.0008 (13) | −0.0008 (12) | −0.0011 (13) |
C9 | 0.0295 (14) | 0.0356 (12) | 0.0343 (12) | −0.0006 (10) | 0.0077 (9) | −0.0010 (9) |
C10 | 0.0354 (15) | 0.0373 (12) | 0.0328 (11) | 0.0004 (10) | 0.0012 (10) | −0.0014 (9) |
Geometric parameters (Å, º) top
O1—C2 | 1.341 (3) | C5—C10 | 1.392 (3) |
O1—C9 | 1.408 (3) | C5—C6 | 1.412 (3) |
O6—C6 | 1.372 (3) | C5—C51 | 1.520 (4) |
O2—C2 | 1.210 (3) | C6—C7 | 1.397 (4) |
C2—C3 | 1.485 (4) | C7—C8 | 1.387 (3) |
C3—C4 | 1.540 (4) | C7—C71 | 1.513 (3) |
C4—C41 | 1.534 (5) | C8—C9 | 1.400 (3) |
C4—C10 | 1.538 (3) | C8—C81 | 1.502 (4) |
C4—C42 | 1.541 (4) | C9—C10 | 1.398 (4) |
| | | |
C2—O1—C9 | 121.1 (2) | O6—C6—C5 | 116.0 (2) |
O2—C2—O1 | 116.9 (3) | C7—C6—C5 | 122.4 (2) |
O2—C2—C3 | 127.2 (2) | C8—C7—C6 | 119.0 (2) |
O1—C2—C3 | 115.9 (2) | C8—C7—C71 | 121.8 (2) |
C2—C3—C4 | 112.7 (2) | C6—C7—C71 | 119.2 (2) |
C41—C4—C10 | 115.4 (3) | C7—C8—C9 | 118.0 (2) |
C41—C4—C3 | 104.6 (3) | C7—C8—C81 | 122.6 (2) |
C10—C4—C3 | 107.3 (2) | C9—C8—C81 | 119.4 (2) |
C41—C4—C42 | 110.3 (3) | C8—C9—C10 | 124.1 (2) |
C10—C4—C42 | 109.7 (2) | C8—C9—O1 | 113.6 (2) |
C3—C4—C42 | 109.4 (3) | C10—C9—O1 | 122.1 (2) |
C10—C5—C6 | 118.9 (2) | C5—C10—C9 | 117.5 (2) |
C10—C5—C51 | 124.8 (2) | C5—C10—C4 | 125.6 (2) |
C6—C5—C51 | 116.3 (2) | C9—C10—C4 | 116.8 (2) |
O6—C6—C7 | 121.5 (2) | | |
| | | |
C9—O1—C2—O2 | −175.4 (2) | C81—C8—C9—C10 | −178.8 (2) |
C9—O1—C2—C3 | 5.8 (3) | C7—C8—C9—O1 | −173.98 (18) |
O2—C2—C3—C4 | 137.0 (3) | C81—C8—C9—O1 | 6.4 (3) |
O1—C2—C3—C4 | −44.4 (3) | C2—O1—C9—C8 | −163.7 (2) |
C2—C3—C4—C41 | 177.0 (3) | C2—O1—C9—C10 | 21.4 (3) |
C2—C3—C4—C10 | 54.0 (3) | C6—C5—C10—C9 | 3.5 (3) |
C2—C3—C4—C42 | −64.9 (3) | C51—C5—C10—C9 | −173.6 (3) |
C10—C5—C6—O6 | 178.5 (2) | C6—C5—C10—C4 | −178.3 (2) |
C51—C5—C6—O6 | −4.2 (3) | C51—C5—C10—C4 | 4.6 (4) |
C10—C5—C6—C7 | −2.0 (3) | C8—C9—C10—C5 | −3.1 (3) |
C51—C5—C6—C7 | 175.3 (2) | O1—C9—C10—C5 | 171.3 (2) |
O6—C6—C7—C8 | 179.20 (19) | C8—C9—C10—C4 | 178.6 (2) |
C5—C6—C7—C8 | −0.3 (3) | O1—C9—C10—C4 | −7.0 (3) |
O6—C6—C7—C71 | 0.6 (3) | C41—C4—C10—C5 | 36.7 (4) |
C5—C6—C7—C71 | −178.9 (2) | C3—C4—C10—C5 | 152.7 (2) |
C6—C7—C8—C9 | 0.9 (3) | C42—C4—C10—C5 | −88.6 (3) |
C71—C7—C8—C9 | 179.4 (2) | C41—C4—C10—C9 | −145.1 (3) |
C6—C7—C8—C81 | −179.5 (2) | C3—C4—C10—C9 | −29.1 (3) |
C71—C7—C8—C81 | −0.9 (3) | C42—C4—C10—C9 | 89.6 (3) |
C7—C8—C9—C10 | 0.8 (3) | | |
(cum224) 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin
top
Crystal data top
C14H18O3 | V = 1277.6 (3) Å3 |
Mr = 234.28 | Z = 4 |
P21/n, monoclinic | F(000) = 504 |
a = 13.341 (2) Å | Dx = 1.218 Mg m−3 |
b = 6.857 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 13.969 (2) Å | µ = 0.08 mm−1 |
α = 90° | T = 224 K |
β = 91.18 (2)° | , colourlees |
γ = 90° | 0.44 × 0.38 × 0.12 mm |
Data collection top
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 29.6°, θmin = 3.3° |
6101 measured reflections | h = −15→16 |
2984 independent reflections | k = −9→9 |
964 reflections with I > 2σ(I) | l = −14→18 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.064 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.188 | w = 1/[σ2(Fo2) + (0.078P)2 + 0.099P] where P = (Fo2 + 2Fc2)/3 |
S = 0.94 | (Δ/σ)max < 0.001 |
2984 reflections | Δρmax = 0.40 e Å−3 |
227 parameters | Δρmin = −0.31 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0024 (16) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.79833 (14) | 0.2123 (3) | −0.30442 (13) | 0.0458 (6) | |
O6 | 1.15996 (14) | 0.2499 (3) | −0.48387 (15) | 0.0490 (6) | |
H6 | 1.162 (2) | 0.266 (4) | −0.557 (2) | 0.076 (11)* | |
O2 | 0.70221 (18) | 0.2113 (4) | −0.18018 (16) | 0.0721 (8) | |
C2 | 0.7841 (2) | 0.2468 (4) | −0.2112 (2) | 0.0497 (8) | |
C3 | 0.8713 (3) | 0.3321 (6) | −0.1580 (2) | 0.0580 (10) | |
H3A | 0.854 (2) | 0.321 (4) | −0.091 (2) | 0.071 (10)* | |
H3B | 0.883 (2) | 0.480 (5) | −0.180 (2) | 0.071 (10)* | |
C4 | 0.9707 (2) | 0.2322 (4) | −0.18200 (19) | 0.0482 (8) | |
C41 | 1.0504 (4) | 0.3465 (9) | −0.1243 (3) | 0.0830 (14) | |
H41A | 1.023 (3) | 0.369 (5) | −0.067 (3) | 0.084 (12)* | |
H41B | 1.063 (2) | 0.476 (4) | −0.1538 (19) | 0.048 (10)* | |
H41C | 1.117 (4) | 0.262 (6) | −0.122 (4) | 0.15 (2)* | |
C42 | 0.9682 (4) | 0.0172 (7) | −0.1470 (3) | 0.0823 (14) | |
H42A | 0.957 (3) | 0.009 (5) | −0.078 (3) | 0.110 (14)* | |
H42B | 1.039 (3) | −0.036 (6) | −0.160 (2) | 0.102 (14)* | |
H42C | 0.911 (3) | −0.070 (6) | −0.191 (3) | 0.123 (16)* | |
C5 | 1.0713 (2) | 0.2370 (4) | −0.33965 (19) | 0.0374 (7) | |
C51 | 1.1745 (3) | 0.2175 (7) | −0.2926 (3) | 0.0593 (10) | |
H51A | 1.214 (3) | 0.155 (6) | −0.344 (3) | 0.130 (16)* | |
H51B | 1.175 (2) | 0.118 (4) | −0.237 (2) | 0.061 (10)* | |
H51C | 1.202 (3) | 0.343 (6) | −0.269 (3) | 0.122 (17)* | |
C6 | 1.0687 (2) | 0.2470 (4) | −0.44012 (18) | 0.0343 (6) | |
C7 | 0.9792 (2) | 0.2519 (4) | −0.49352 (18) | 0.0354 (7) | |
C71 | 0.9818 (3) | 0.2591 (5) | −0.6018 (2) | 0.0454 (8) | |
H71A | 1.021 (2) | 0.157 (4) | −0.626 (2) | 0.062 (10)* | |
H71B | 1.021 (2) | 0.374 (4) | −0.6195 (19) | 0.065 (10)* | |
H71C | 0.908 (3) | 0.265 (5) | −0.632 (3) | 0.107 (14)* | |
C8 | 0.8889 (2) | 0.2459 (4) | −0.44592 (17) | 0.0345 (6) | |
C81 | 0.7888 (2) | 0.2491 (6) | −0.4975 (2) | 0.0481 (8) | |
H81A | 0.784 (3) | 0.352 (5) | −0.542 (3) | 0.106 (14)* | |
H81B | 0.732 (4) | 0.279 (6) | −0.451 (4) | 0.153 (19)* | |
H81C | 0.775 (3) | 0.132 (6) | −0.533 (3) | 0.129 (17)* | |
C9 | 0.8929 (2) | 0.2380 (4) | −0.34588 (18) | 0.0350 (7) | |
C10 | 0.9814 (2) | 0.2380 (4) | −0.29090 (18) | 0.0368 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0376 (13) | 0.0642 (14) | 0.0361 (10) | −0.0032 (10) | 0.0109 (8) | −0.0016 (10) |
O6 | 0.0379 (13) | 0.0570 (13) | 0.0527 (13) | 0.0025 (11) | 0.0147 (10) | 0.0016 (11) |
O2 | 0.0568 (17) | 0.1007 (19) | 0.0600 (14) | −0.0079 (14) | 0.0278 (12) | −0.0062 (13) |
C2 | 0.047 (2) | 0.061 (2) | 0.0417 (17) | 0.0111 (18) | 0.0186 (15) | 0.0022 (16) |
C3 | 0.053 (2) | 0.085 (3) | 0.0368 (19) | 0.0013 (19) | 0.0048 (16) | −0.0100 (19) |
C4 | 0.046 (2) | 0.062 (2) | 0.0368 (16) | 0.0078 (17) | 0.0005 (13) | −0.0047 (16) |
C41 | 0.075 (3) | 0.117 (4) | 0.056 (3) | 0.005 (3) | −0.006 (2) | −0.029 (3) |
C42 | 0.105 (4) | 0.091 (3) | 0.051 (2) | 0.021 (3) | 0.016 (2) | 0.022 (2) |
C5 | 0.0324 (18) | 0.0375 (16) | 0.0423 (16) | 0.0014 (13) | 0.0006 (12) | −0.0023 (13) |
C51 | 0.046 (2) | 0.075 (3) | 0.056 (2) | 0.007 (2) | −0.0039 (17) | 0.001 (2) |
C6 | 0.0318 (17) | 0.0294 (15) | 0.0420 (15) | 0.0013 (13) | 0.0089 (12) | −0.0011 (13) |
C7 | 0.0412 (18) | 0.0310 (14) | 0.0343 (14) | 0.0006 (15) | 0.0060 (12) | −0.0024 (12) |
C71 | 0.051 (2) | 0.048 (2) | 0.0378 (16) | 0.003 (2) | 0.0137 (15) | −0.0004 (15) |
C8 | 0.0359 (17) | 0.0320 (15) | 0.0357 (15) | −0.0016 (13) | 0.0022 (11) | −0.0001 (13) |
C81 | 0.043 (2) | 0.058 (2) | 0.0427 (18) | 0.0028 (19) | −0.0049 (14) | 0.0036 (19) |
C9 | 0.0336 (17) | 0.0363 (15) | 0.0355 (14) | −0.0021 (14) | 0.0087 (12) | −0.0004 (13) |
C10 | 0.0354 (18) | 0.0391 (16) | 0.0359 (15) | 0.0016 (14) | 0.0024 (12) | −0.0006 (13) |
Geometric parameters (Å, º) top
O1—C2 | 1.341 (3) | C5—C10 | 1.392 (4) |
O1—C9 | 1.411 (3) | C5—C6 | 1.405 (4) |
O6—C6 | 1.374 (3) | C5—C51 | 1.519 (4) |
O2—C2 | 1.208 (3) | C6—C7 | 1.395 (4) |
C2—C3 | 1.488 (5) | C7—C8 | 1.389 (4) |
C3—C4 | 1.536 (4) | C7—C71 | 1.514 (4) |
C4—C10 | 1.531 (4) | C8—C9 | 1.399 (3) |
C4—C41 | 1.536 (5) | C8—C81 | 1.505 (4) |
C4—C42 | 1.553 (5) | C9—C10 | 1.394 (4) |
| | | |
C2—O1—C9 | 121.5 (2) | O6—C6—C5 | 116.1 (2) |
O2—C2—O1 | 117.4 (3) | C7—C6—C5 | 122.6 (2) |
O2—C2—C3 | 127.1 (3) | C8—C7—C6 | 119.0 (2) |
O1—C2—C3 | 115.4 (3) | C8—C7—C71 | 121.2 (3) |
C2—C3—C4 | 112.7 (3) | C6—C7—C71 | 119.9 (3) |
C10—C4—C41 | 115.5 (3) | C7—C8—C9 | 117.6 (2) |
C10—C4—C3 | 107.6 (2) | C7—C8—C81 | 122.7 (2) |
C41—C4—C3 | 104.4 (3) | C9—C8—C81 | 119.7 (3) |
C10—C4—C42 | 109.9 (3) | C10—C9—C8 | 124.4 (2) |
C41—C4—C42 | 109.8 (4) | C10—C9—O1 | 121.9 (2) |
C3—C4—C42 | 109.3 (3) | C8—C9—O1 | 113.5 (2) |
C10—C5—C6 | 119.0 (2) | C5—C10—C9 | 117.3 (2) |
C10—C5—C51 | 124.8 (3) | C5—C10—C4 | 125.7 (2) |
C6—C5—C51 | 116.2 (3) | C9—C10—C4 | 116.9 (2) |
O6—C6—C7 | 121.2 (2) | | |
| | | |
C9—O1—C2—O2 | −176.1 (2) | C81—C8—C9—C10 | −178.8 (3) |
C9—O1—C2—C3 | 5.9 (4) | C7—C8—C9—O1 | −173.9 (2) |
O2—C2—C3—C4 | 138.0 (3) | C81—C8—C9—O1 | 6.5 (4) |
O1—C2—C3—C4 | −44.3 (4) | C2—O1—C9—C10 | 21.1 (4) |
C2—C3—C4—C10 | 54.1 (4) | C2—O1—C9—C8 | −164.1 (3) |
C2—C3—C4—C41 | 177.4 (3) | C6—C5—C10—C9 | 3.5 (4) |
C2—C3—C4—C42 | −65.2 (4) | C51—C5—C10—C9 | −173.9 (3) |
C10—C5—C6—O6 | 178.6 (2) | C6—C5—C10—C4 | −178.7 (3) |
C51—C5—C6—O6 | −3.7 (4) | C51—C5—C10—C4 | 3.9 (5) |
C10—C5—C6—C7 | −2.1 (4) | C8—C9—C10—C5 | −3.0 (4) |
C51—C5—C6—C7 | 175.6 (3) | O1—C9—C10—C5 | 171.2 (2) |
O6—C6—C7—C8 | 179.1 (2) | C8—C9—C10—C4 | 179.0 (2) |
C5—C6—C7—C8 | −0.2 (4) | O1—C9—C10—C4 | −6.8 (4) |
O6—C6—C7—C71 | 0.4 (4) | C41—C4—C10—C5 | 36.8 (5) |
C5—C6—C7—C71 | −178.9 (3) | C3—C4—C10—C5 | 153.0 (3) |
C6—C7—C8—C9 | 0.9 (4) | C42—C4—C10—C5 | −88.1 (4) |
C71—C7—C8—C9 | 179.5 (3) | C41—C4—C10—C9 | −145.4 (3) |
C6—C7—C8—C81 | −179.6 (3) | C3—C4—C10—C9 | −29.2 (4) |
C71—C7—C8—C81 | −0.9 (4) | C42—C4—C10—C9 | 89.7 (4) |
C7—C8—C9—C10 | 0.8 (4) | | |
(cum225c) 6-hydroxhy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin
top
Crystal data top
C14H18O3 | V = 1275.8 (10) Å3 |
Mr = 234.28 | Z = 4 |
P21/c, monoclinic | F(000) = 504 |
a = 9.760 (7) Å | Dx = 1.220 Mg m−3 |
b = 6.863 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 19.113 (4) Å | µ = 0.09 mm−1 |
α = 90° | T = 225 K |
β = 94.75 (4)° | , colourlees |
γ = 90° | 0.30 × 0.25 × 0.12 mm |
Data collection top
Radiation source: fine-focus sealed tube | Rint = 0.052 |
Graphite monochromator | θmax = 29.5°, θmin = 3.6° |
7747 measured reflections | h = −13→13 |
3276 independent reflections | k = −9→5 |
955 reflections with I > 2σ(I) | l = −26→25 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.012P)2 + 0.093P] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max = 0.003 |
3276 reflections | Δρmax = 0.25 e Å−3 |
216 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0116 (5) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.10284 (13) | 0.2346 (2) | 0.24735 (7) | 0.0432 (4) | |
O2 | −0.11655 (16) | 0.2357 (3) | 0.26180 (9) | 0.0735 (6) | |
O6 | 0.65080 (13) | 0.2618 (3) | 0.33863 (8) | 0.0463 (5) | |
H6 | 0.711 (2) | 0.253 (4) | 0.3040 (10) | 0.065* | |
C2 | −0.0016 (3) | 0.2707 (4) | 0.28681 (14) | 0.0489 (7) | |
C3 | 0.0369 (3) | 0.3631 (4) | 0.35565 (15) | 0.0542 (8) | |
H3A | −0.050 (2) | 0.359 (3) | 0.3852 (11) | 0.076* | |
H3B | 0.073 (2) | 0.513 (3) | 0.3462 (11) | 0.076* | |
C4 | 0.1646 (2) | 0.2689 (4) | 0.39527 (12) | 0.0469 (7) | |
C41 | 0.1961 (4) | 0.3998 (6) | 0.46048 (17) | 0.0951 (14) | |
H41A | 0.107 (3) | 0.405 (4) | 0.4821 (15) | 0.133* | |
H41B | 0.226 (3) | 0.535 (4) | 0.4466 (16) | 0.133* | |
H41C | 0.260 (3) | 0.335 (4) | 0.4968 (15) | 0.133* | |
C42 | 0.1287 (4) | 0.0598 (6) | 0.4171 (2) | 0.0931 (12) | |
H42A | 0.218 (3) | −0.011 (4) | 0.4438 (14) | 0.130* | |
H42B | 0.106 (3) | −0.022 (4) | 0.3670 (15) | 0.130* | |
H42C | 0.058 (3) | 0.072 (4) | 0.4459 (14) | 0.130* | |
C5 | 0.4206 (2) | 0.2584 (3) | 0.36639 (11) | 0.0327 (6) | |
C51 | 0.4806 (3) | 0.2385 (5) | 0.44137 (13) | 0.0553 (8) | |
H51A | 0.419 (2) | 0.158 (3) | 0.4715 (12) | 0.083* | |
H51B | 0.498 (2) | 0.370 (4) | 0.4661 (11) | 0.083* | |
H51C | 0.581 (2) | 0.178 (3) | 0.4432 (11) | 0.083* | |
C6 | 0.5135 (2) | 0.2621 (3) | 0.31470 (11) | 0.0305 (6) | |
C7 | 0.47309 (19) | 0.2658 (3) | 0.24311 (11) | 0.0296 (5) | |
C71 | 0.5795 (3) | 0.2682 (5) | 0.19065 (16) | 0.0436 (7) | |
H71A | 0.544 (2) | 0.277 (3) | 0.1408 (12) | 0.075 (9)* | |
H71B | 0.639 (3) | 0.156 (4) | 0.1938 (13) | 0.094 (11)* | |
H71C | 0.651 (2) | 0.367 (3) | 0.2007 (12) | 0.081 (10)* | |
C8 | 0.33261 (19) | 0.2612 (3) | 0.22211 (10) | 0.0289 (5) | |
C81 | 0.2798 (3) | 0.2582 (6) | 0.14532 (14) | 0.0459 (7) | |
H81A | 0.308 (3) | 0.135 (5) | 0.1218 (14) | 0.130 (14)* | |
H81B | 0.317 (2) | 0.354 (4) | 0.1216 (12) | 0.080 (12)* | |
H81C | 0.173 (3) | 0.256 (4) | 0.1410 (13) | 0.121 (11)* | |
C9 | 0.24245 (19) | 0.2597 (3) | 0.27472 (11) | 0.0308 (6) | |
C10 | 0.2798 (2) | 0.2632 (3) | 0.34630 (11) | 0.0327 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0227 (8) | 0.0618 (11) | 0.0453 (10) | −0.0032 (10) | 0.0041 (8) | −0.0036 (11) |
O2 | 0.0238 (9) | 0.1023 (15) | 0.0946 (14) | −0.0046 (13) | 0.0064 (10) | −0.0120 (14) |
O6 | 0.0273 (10) | 0.0528 (11) | 0.0575 (11) | 0.0006 (11) | −0.0032 (8) | −0.0013 (12) |
C2 | 0.0347 (15) | 0.0564 (19) | 0.0570 (18) | 0.0049 (18) | 0.0128 (14) | 0.0045 (19) |
C3 | 0.0336 (16) | 0.085 (2) | 0.0459 (19) | 0.0085 (16) | 0.0117 (15) | 0.0001 (17) |
C4 | 0.0401 (15) | 0.062 (2) | 0.0404 (15) | 0.0074 (17) | 0.0142 (13) | 0.0081 (18) |
C41 | 0.075 (3) | 0.162 (4) | 0.050 (2) | 0.042 (3) | 0.010 (2) | −0.026 (3) |
C42 | 0.074 (2) | 0.098 (3) | 0.114 (3) | 0.015 (2) | 0.049 (2) | 0.052 (2) |
C5 | 0.0330 (13) | 0.0327 (14) | 0.0319 (13) | 0.0025 (15) | −0.0005 (11) | −0.0015 (16) |
C51 | 0.0525 (17) | 0.068 (2) | 0.0439 (18) | 0.0034 (19) | −0.0047 (14) | −0.0040 (19) |
C6 | 0.0248 (13) | 0.0196 (13) | 0.0462 (15) | 0.0002 (14) | −0.0027 (11) | −0.0027 (15) |
C7 | 0.0271 (13) | 0.0230 (13) | 0.0397 (15) | 0.0019 (14) | 0.0087 (11) | 0.0005 (15) |
C71 | 0.0321 (15) | 0.046 (2) | 0.0544 (19) | −0.0001 (18) | 0.0152 (14) | −0.001 (2) |
C8 | 0.0295 (12) | 0.0254 (14) | 0.0319 (14) | −0.0024 (14) | 0.0018 (11) | −0.0016 (15) |
C81 | 0.0479 (18) | 0.055 (2) | 0.0351 (16) | −0.008 (2) | 0.0058 (14) | −0.002 (2) |
C9 | 0.0184 (12) | 0.0330 (14) | 0.0410 (14) | −0.0006 (14) | 0.0021 (10) | 0.0014 (16) |
C10 | 0.0310 (13) | 0.0374 (15) | 0.0299 (13) | −0.0003 (15) | 0.0037 (11) | 0.0032 (15) |
Geometric parameters (Å, º) top
O1—C2 | 1.341 (2) | C5—C6 | 1.396 (3) |
O1—C9 | 1.429 (2) | C5—C10 | 1.396 (3) |
O2—C2 | 1.206 (3) | C5—C51 | 1.509 (3) |
O6—C6 | 1.380 (2) | C51—H51A | 1.03 (2) |
O6—H6 | 0.92 (2) | C51—H51B | 1.03 (2) |
C2—C3 | 1.480 (3) | C51—H51C | 1.06 (2) |
C3—C4 | 1.546 (3) | C6—C7 | 1.393 (2) |
C3—H3A | 1.06 (2) | C7—C8 | 1.397 (3) |
C3—H3B | 1.11 (2) | C7—C71 | 1.502 (3) |
C4—C10 | 1.521 (3) | C71—H71A | 0.99 (2) |
C4—C42 | 1.544 (4) | C71—H71B | 0.96 (2) |
C4—C41 | 1.546 (4) | C71—H71C | 0.98 (2) |
C41—H41A | 1.00 (3) | C8—C9 | 1.390 (2) |
C41—H41B | 1.02 (3) | C8—C81 | 1.515 (3) |
C41—H41C | 1.00 (3) | C81—H81A | 1.00 (3) |
C42—H42A | 1.09 (3) | C81—H81B | 0.89 (2) |
C42—H42B | 1.12 (3) | C81—H81C | 1.04 (2) |
C42—H42C | 0.92 (3) | C9—C10 | 1.387 (2) |
| | | |
C2—O1—C9 | 121.21 (18) | C5—C51—H51B | 113.2 (13) |
C6—O6—H6 | 114.9 (14) | H51A—C51—H51B | 107.2 (19) |
O2—C2—O1 | 117.7 (2) | C5—C51—H51C | 110.5 (12) |
O2—C2—C3 | 126.6 (2) | H51A—C51—H51C | 110.5 (18) |
O1—C2—C3 | 115.5 (2) | H51B—C51—H51C | 102.3 (18) |
C2—C3—C4 | 113.0 (2) | O6—C6—C7 | 120.9 (2) |
C2—C3—H3A | 107.9 (11) | O6—C6—C5 | 115.8 (2) |
C4—C3—H3A | 112.3 (11) | C7—C6—C5 | 123.2 (2) |
C2—C3—H3B | 108.2 (11) | C6—C7—C8 | 118.2 (2) |
C4—C3—H3B | 102.5 (12) | C6—C7—C71 | 120.1 (2) |
H3A—C3—H3B | 112.8 (18) | C8—C7—C71 | 121.7 (2) |
C10—C4—C42 | 109.8 (2) | C7—C71—H71A | 115.9 (13) |
C10—C4—C3 | 108.45 (19) | C7—C71—H71B | 113.3 (16) |
C42—C4—C3 | 109.2 (2) | H71A—C71—H71B | 106 (2) |
C10—C4—C41 | 113.8 (2) | C7—C71—H71C | 113.3 (15) |
C42—C4—C41 | 110.9 (3) | H71A—C71—H71C | 109 (2) |
C3—C4—C41 | 104.5 (2) | H71B—C71—H71C | 97.2 (17) |
C4—C41—H41A | 103.4 (17) | C9—C8—C7 | 117.2 (2) |
C4—C41—H41B | 111.3 (18) | C9—C8—C81 | 121.0 (2) |
H41A—C41—H41B | 111 (3) | C7—C8—C81 | 121.7 (2) |
C4—C41—H41C | 111.9 (18) | C8—C81—H81A | 111.3 (16) |
H41A—C41—H41C | 104 (2) | C8—C81—H81B | 111.1 (16) |
H41B—C41—H41C | 114 (3) | H81A—C81—H81B | 105 (2) |
C4—C42—H42A | 110.6 (15) | C8—C81—H81C | 109.6 (14) |
C4—C42—H42B | 105.6 (16) | H81A—C81—H81C | 105 (2) |
H42A—C42—H42B | 106 (2) | H81B—C81—H81C | 115 (2) |
C4—C42—H42C | 106 (2) | C10—C9—C8 | 125.69 (19) |
H42A—C42—H42C | 112 (2) | C10—C9—O1 | 121.86 (19) |
H42B—C42—H42C | 117 (3) | C8—C9—O1 | 112.19 (18) |
C6—C5—C10 | 119.2 (2) | C9—C10—C5 | 116.3 (2) |
C6—C5—C51 | 116.7 (2) | C9—C10—C4 | 117.41 (19) |
C10—C5—C51 | 124.0 (2) | C5—C10—C4 | 126.3 (2) |
C5—C51—H51A | 112.6 (13) | | |
| | | |
C9—O1—C2—O2 | −175.8 (3) | C81—C8—C9—C10 | −179.6 (3) |
C9—O1—C2—C3 | 8.2 (3) | C7—C8—C9—O1 | −173.9 (2) |
O2—C2—C3—C4 | 139.7 (3) | C81—C8—C9—O1 | 6.2 (4) |
O1—C2—C3—C4 | −44.7 (3) | C2—O1—C9—C10 | 20.1 (3) |
C2—C3—C4—C10 | 52.1 (3) | C2—O1—C9—C8 | −165.4 (2) |
C2—C3—C4—C42 | −67.5 (3) | C8—C9—C10—C5 | −3.2 (4) |
C2—C3—C4—C41 | 173.9 (2) | O1—C9—C10—C5 | 170.4 (2) |
C10—C5—C6—O6 | 178.5 (2) | C8—C9—C10—C4 | 177.6 (2) |
C51—C5—C6—O6 | −4.7 (3) | O1—C9—C10—C4 | −8.7 (4) |
C10—C5—C6—C7 | −1.6 (4) | C6—C5—C10—C9 | 3.7 (4) |
C51—C5—C6—C7 | 175.3 (2) | C51—C5—C10—C9 | −172.9 (3) |
O6—C6—C7—C8 | 178.5 (2) | C6—C5—C10—C4 | −177.2 (2) |
C5—C6—C7—C8 | −1.5 (4) | C51—C5—C10—C4 | 6.2 (4) |
O6—C6—C7—C71 | 0.4 (4) | C42—C4—C10—C9 | 93.3 (3) |
C5—C6—C7—C71 | −179.6 (2) | C3—C4—C10—C9 | −25.9 (3) |
C6—C7—C8—C9 | 2.1 (4) | C41—C4—C10—C9 | −141.8 (3) |
C71—C7—C8—C9 | −179.9 (3) | C42—C4—C10—C5 | −85.8 (3) |
C6—C7—C8—C81 | −178.0 (3) | C3—C4—C10—C5 | 155.0 (3) |
C71—C7—C8—C81 | 0.0 (4) | C41—C4—C10—C5 | 39.2 (4) |
C7—C8—C9—C10 | 0.3 (4) | | |
(cum230) 6-hydroxy-4,4,5,7,8-pentamathyl-3,4-dihydrocoumarin
top
Crystal data top
C14H18O3 | V = 1279.6 (2) Å3 |
Mr = 234.28 | Z = 4 |
P21/c, monoclinic | F(000) = 504 |
a = 9.758 (1) Å | Dx = 1.216 Mg m−3 |
b = 6.883 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 19.117 (1) Å | µ = 0.08 mm−1 |
α = 90° | T = 230 K |
β = 94.75 (1)° | , colourlees |
γ = 90° | 0.44 × 0.38 × 0.12 mm |
Data collection top
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 29.6°, θmin = 3.7° |
7607 measured reflections | h = −6→13 |
3249 independent reflections | k = −9→9 |
1648 reflections with I > 2σ(I) | l = −25→24 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.216 | w = 1/[σ2(Fo2) + (0.1275P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 2.962 |
3249 reflections | Δρmax = 0.40 e Å−3 |
232 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.000 (6) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.10309 (13) | 0.23474 (19) | 0.24743 (7) | 0.0436 (4) | |
O2 | −0.11600 (16) | 0.2348 (3) | 0.26197 (11) | 0.0729 (6) | |
O6 | 0.65074 (14) | 0.26179 (19) | 0.33880 (9) | 0.0456 (4) | |
H6 | 0.713 (3) | 0.252 (3) | 0.3033 (17) | 0.081 (9)* | |
C2 | −0.0015 (2) | 0.2719 (3) | 0.28711 (13) | 0.0488 (6) | |
C3 | 0.0379 (2) | 0.3627 (4) | 0.35639 (13) | 0.0552 (7) | 0.99 |
H3A | −0.045 (3) | 0.351 (4) | 0.3837 (14) | 0.079 (8)* | 0.99 |
H3B | 0.056 (2) | 0.494 (4) | 0.3473 (13) | 0.068 (8)* | 0.99 |
C3' | 0.037 (9) | 0.144 (13) | 0.356 (5) | 0.000 (16)* | 0.01 |
C4 | 0.1644 (2) | 0.2684 (3) | 0.39596 (11) | 0.0491 (6) | |
C41 | 0.1971 (4) | 0.4010 (7) | 0.46021 (16) | 0.0943 (13) | |
H41A | 0.106 (3) | 0.410 (4) | 0.4806 (14) | 0.090 (8)* | |
H41B | 0.230 (5) | 0.534 (7) | 0.447 (3) | 0.20 (3)* | |
H41C | 0.258 (4) | 0.311 (5) | 0.499 (2) | 0.111 (11)* | |
C42 | 0.1277 (3) | 0.0584 (6) | 0.4159 (2) | 0.0918 (12) | |
H42A | 0.050 (3) | 0.068 (4) | 0.4461 (16) | 0.102 (10)* | |
H42B | 0.208 (3) | 0.014 (4) | 0.4468 (15) | 0.094 (9)* | |
H42C | 0.100 (5) | −0.028 (7) | 0.367 (3) | 0.179 (19)* | |
C5 | 0.42090 (19) | 0.2590 (2) | 0.36647 (10) | 0.0338 (4) | |
C51 | 0.4819 (3) | 0.2403 (4) | 0.44171 (12) | 0.0536 (6) | |
H51A | 0.425 (3) | 0.144 (4) | 0.4663 (15) | 0.092 (9)* | |
H51B | 0.507 (4) | 0.363 (5) | 0.4591 (19) | 0.128 (13)* | |
H51C | 0.574 (4) | 0.187 (5) | 0.4406 (16) | 0.098 (10)* | |
C6 | 0.51452 (17) | 0.2632 (2) | 0.31477 (10) | 0.0329 (4) | |
C7 | 0.47264 (17) | 0.2663 (2) | 0.24286 (10) | 0.0307 (4) | |
C71 | 0.5801 (2) | 0.2682 (3) | 0.19032 (12) | 0.0416 (5) | |
H71A | 0.534 (3) | 0.283 (4) | 0.1425 (18) | 0.094 (10)* | |
H71B | 0.638 (2) | 0.155 (4) | 0.1918 (11) | 0.063 (7)* | |
H71C | 0.649 (3) | 0.373 (4) | 0.1983 (12) | 0.068 (7)* | |
C8 | 0.33320 (18) | 0.2620 (2) | 0.22171 (9) | 0.0307 (4) | |
C81 | 0.2790 (2) | 0.2600 (3) | 0.14553 (11) | 0.0439 (5) | |
H81A | 0.306 (3) | 0.143 (4) | 0.1227 (15) | 0.089 (9)* | |
H81B | 0.319 (3) | 0.371 (5) | 0.1201 (17) | 0.120 (12)* | |
H81C | 0.180 (4) | 0.280 (4) | 0.1377 (18) | 0.107 (11)* | |
C9 | 0.24049 (18) | 0.2592 (2) | 0.27410 (10) | 0.0316 (4) | |
C10 | 0.28022 (19) | 0.2636 (2) | 0.34596 (10) | 0.0334 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0218 (7) | 0.0634 (9) | 0.0456 (8) | −0.0028 (5) | 0.0030 (6) | −0.0033 (6) |
O2 | 0.0249 (8) | 0.1037 (15) | 0.0907 (14) | −0.0037 (7) | 0.0077 (8) | −0.0136 (10) |
O6 | 0.0257 (7) | 0.0534 (9) | 0.0567 (9) | 0.0008 (5) | −0.0035 (6) | −0.0047 (6) |
C2 | 0.0239 (9) | 0.0589 (13) | 0.0645 (14) | 0.0023 (8) | 0.0097 (9) | 0.0033 (10) |
C3 | 0.0395 (12) | 0.0706 (18) | 0.0574 (14) | 0.0114 (11) | 0.0164 (10) | 0.0014 (13) |
C4 | 0.0418 (12) | 0.0684 (15) | 0.0392 (11) | 0.0097 (9) | 0.0149 (9) | 0.0069 (10) |
C41 | 0.073 (2) | 0.160 (4) | 0.0504 (16) | 0.050 (2) | 0.0103 (14) | −0.024 (2) |
C42 | 0.0639 (18) | 0.112 (3) | 0.105 (3) | 0.0120 (17) | 0.0379 (19) | 0.058 (2) |
C5 | 0.0332 (10) | 0.0319 (10) | 0.0359 (10) | 0.0029 (7) | −0.0004 (7) | −0.0009 (7) |
C51 | 0.0499 (14) | 0.0700 (17) | 0.0392 (12) | 0.0081 (12) | −0.0063 (10) | −0.0021 (11) |
C6 | 0.0244 (9) | 0.0300 (9) | 0.0439 (10) | 0.0009 (6) | 0.0000 (7) | −0.0023 (7) |
C7 | 0.0257 (9) | 0.0282 (9) | 0.0390 (10) | −0.0016 (6) | 0.0067 (7) | −0.0014 (7) |
C71 | 0.0306 (10) | 0.0430 (12) | 0.0533 (13) | 0.0007 (8) | 0.0149 (9) | 0.0026 (9) |
C8 | 0.0291 (9) | 0.0305 (9) | 0.0328 (9) | −0.0002 (6) | 0.0042 (7) | 0.0000 (7) |
C81 | 0.0410 (12) | 0.0568 (14) | 0.0339 (10) | −0.0015 (9) | 0.0034 (8) | 0.0003 (9) |
C9 | 0.0231 (8) | 0.0341 (10) | 0.0377 (10) | −0.0006 (6) | 0.0024 (7) | −0.0018 (7) |
C10 | 0.0315 (9) | 0.0352 (10) | 0.0340 (10) | 0.0008 (7) | 0.0065 (7) | −0.0005 (7) |
Geometric parameters (Å, º) top
O1—C2 | 1.345 (2) | C42—H42B | 0.99 (3) |
O1—C9 | 1.405 (2) | C42—H42C | 1.13 (5) |
O2—C2 | 1.207 (3) | C5—C10 | 1.396 (3) |
O6—C6 | 1.370 (2) | C5—C6 | 1.401 (3) |
O6—H6 | 0.95 (3) | C5—C51 | 1.516 (3) |
C2—C3 | 1.486 (3) | C51—H51A | 1.00 (3) |
C2—C3' | 1.61 (9) | C51—H51B | 0.93 (3) |
C3—C3' | 1.50 (9) | C51—H51C | 0.97 (3) |
C3—C4 | 1.537 (3) | C6—C7 | 1.401 (3) |
C3—H3A | 1.00 (3) | C7—C8 | 1.387 (2) |
C3—H3B | 0.94 (3) | C7—C71 | 1.511 (3) |
C3'—C42 | 1.51 (9) | C71—H71A | 0.99 (3) |
C3'—C4 | 1.64 (9) | C71—H71B | 0.97 (3) |
C3'—H42C | 1.35 (9) | C71—H71C | 0.99 (3) |
C4—C10 | 1.540 (3) | C8—C9 | 1.404 (2) |
C4—C41 | 1.543 (4) | C8—C81 | 1.508 (3) |
C4—C42 | 1.544 (4) | C81—H81A | 0.97 (3) |
C41—H41A | 1.00 (3) | C81—H81B | 1.00 (4) |
C41—H41B | 1.01 (5) | C81—H81C | 0.98 (4) |
C41—H41C | 1.10 (4) | C9—C10 | 1.397 (3) |
C42—H42A | 0.99 (3) | | |
| | | |
C2—O1—C9 | 121.23 (16) | C3'—C42—H42A | 89 (4) |
C6—O6—H6 | 115 (2) | C4—C42—H42A | 106.5 (17) |
O2—C2—O1 | 117.1 (2) | C3'—C42—H42B | 164 (4) |
O2—C2—C3 | 127.3 (2) | C4—C42—H42B | 104.4 (18) |
O1—C2—C3 | 115.48 (18) | H42A—C42—H42B | 106 (2) |
O2—C2—C3' | 111 (3) | C3'—C42—H42C | 59 (4) |
O1—C2—C3' | 103 (3) | C4—C42—H42C | 110 (2) |
C3—C2—C3' | 58 (3) | H42A—C42—H42C | 112 (3) |
C2—C3—C3' | 65 (3) | H42B—C42—H42C | 117 (3) |
C2—C3—C4 | 113.48 (19) | C10—C5—C6 | 119.01 (17) |
C3'—C3—C4 | 65 (3) | C10—C5—C51 | 124.59 (18) |
C2—C3—H3A | 105.7 (15) | C6—C5—C51 | 116.34 (18) |
C3'—C3—H3A | 85 (4) | C5—C51—H51A | 108.1 (17) |
C4—C3—H3A | 110.9 (15) | C5—C51—H51B | 109 (2) |
C2—C3—H3B | 106.1 (16) | H51A—C51—H51B | 125 (3) |
C3'—C3—H3B | 164 (4) | C5—C51—H51C | 107.5 (18) |
C4—C3—H3B | 109.8 (14) | H51A—C51—H51C | 108 (2) |
H3A—C3—H3B | 111 (2) | H51B—C51—H51C | 98 (3) |
C3—C3'—C42 | 113 (6) | O6—C6—C5 | 115.76 (17) |
C3—C3'—C2 | 57 (3) | O6—C6—C7 | 121.67 (16) |
C42—C3'—C2 | 157 (6) | C5—C6—C7 | 122.56 (16) |
C3—C3'—C4 | 58 (3) | C8—C7—C6 | 119.00 (16) |
C42—C3'—C4 | 58 (3) | C8—C7—C71 | 121.63 (17) |
C2—C3'—C4 | 102 (5) | C6—C7—C71 | 119.35 (16) |
C3—C3'—H42C | 151 (7) | C7—C71—H71A | 109.0 (19) |
C42—C3'—H42C | 46 (4) | C7—C71—H71B | 114.4 (14) |
C2—C3'—H42C | 133 (7) | H71A—C71—H71B | 109 (2) |
C4—C3'—H42C | 94 (5) | C7—C71—H71C | 113.8 (13) |
C3—C4—C10 | 107.72 (17) | H71A—C71—H71C | 109 (2) |
C3—C4—C41 | 104.3 (2) | H71B—C71—H71C | 101 (2) |
C10—C4—C41 | 113.1 (2) | C7—C8—C9 | 117.82 (16) |
C3—C4—C42 | 108.9 (2) | C7—C8—C81 | 122.60 (17) |
C10—C4—C42 | 109.28 (19) | C9—C8—C81 | 119.57 (17) |
C41—C4—C42 | 113.2 (3) | C8—C81—H81A | 110.9 (17) |
C3—C4—C3' | 56 (3) | C8—C81—H81B | 110.2 (19) |
C10—C4—C3' | 106 (3) | H81A—C81—H81B | 106 (3) |
C41—C4—C3' | 141 (3) | C8—C81—H81C | 114 (2) |
C42—C4—C3' | 56 (3) | H81A—C81—H81C | 111 (2) |
C4—C41—H41A | 102.5 (16) | H81B—C81—H81C | 104 (3) |
C4—C41—H41B | 113 (3) | C10—C9—C8 | 123.96 (16) |
H41A—C41—H41B | 110 (3) | C10—C9—O1 | 122.58 (16) |
C4—C41—H41C | 105.3 (18) | C8—C9—O1 | 113.25 (15) |
H41A—C41—H41C | 103 (2) | C5—C10—C9 | 117.51 (16) |
H41B—C41—H41C | 121 (3) | C5—C10—C4 | 125.55 (17) |
C3'—C42—C4 | 65 (3) | C9—C10—C4 | 116.92 (16) |
| | | |
C9—O1—C2—O2 | −175.12 (17) | C2—C3'—C42—C4 | 36 (15) |
C9—O1—C2—C3 | 7.4 (3) | C3—C4—C42—C3' | 21 (4) |
C9—O1—C2—C3' | −53 (3) | C10—C4—C42—C3' | −96 (4) |
O2—C2—C3—C3' | 93 (4) | C41—C4—C42—C3' | 137 (4) |
O1—C2—C3—C3' | −90 (4) | C10—C5—C6—O6 | 178.89 (14) |
O2—C2—C3—C4 | 138.3 (2) | C51—C5—C6—O6 | −3.8 (2) |
O1—C2—C3—C4 | −44.6 (3) | C10—C5—C6—C7 | −1.9 (2) |
C3'—C2—C3—C4 | 45 (4) | C51—C5—C6—C7 | 175.43 (17) |
C2—C3—C3'—C42 | 156 (6) | O6—C6—C7—C8 | 178.16 (14) |
C4—C3—C3'—C42 | 22 (4) | C5—C6—C7—C8 | −1.0 (2) |
C4—C3—C3'—C2 | −134 (3) | O6—C6—C7—C71 | 0.0 (2) |
C2—C3—C3'—C4 | 134 (3) | C5—C6—C7—C71 | −179.22 (16) |
O2—C2—C3'—C3 | −121.8 (17) | C6—C7—C8—C9 | 1.4 (2) |
O1—C2—C3'—C3 | 112.1 (18) | C71—C7—C8—C9 | 179.58 (15) |
O2—C2—C3'—C42 | 169 (15) | C6—C7—C8—C81 | −178.49 (16) |
O1—C2—C3'—C42 | 43 (16) | C71—C7—C8—C81 | −0.3 (2) |
C3—C2—C3'—C42 | −70 (15) | C7—C8—C9—C10 | 1.1 (2) |
O2—C2—C3'—C4 | −160 (3) | C81—C8—C9—C10 | −179.02 (16) |
O1—C2—C3'—C4 | 74 (4) | C7—C8—C9—O1 | −173.80 (13) |
C3—C2—C3'—C4 | −39 (3) | C81—C8—C9—O1 | 6.1 (2) |
C2—C3—C4—C10 | 52.3 (3) | C2—O1—C9—C10 | 20.2 (2) |
C3'—C3—C4—C10 | 97 (4) | C2—O1—C9—C8 | −164.83 (16) |
C2—C3—C4—C41 | 172.7 (3) | C6—C5—C10—C9 | 4.2 (2) |
C3'—C3—C4—C41 | −142 (4) | C51—C5—C10—C9 | −172.90 (18) |
C2—C3—C4—C42 | −66.1 (3) | C6—C5—C10—C4 | −177.37 (16) |
C3'—C3—C4—C42 | −21 (4) | C51—C5—C10—C4 | 5.6 (3) |
C2—C3—C4—C3' | −45 (4) | C8—C9—C10—C5 | −3.9 (2) |
C42—C3'—C4—C3 | −156 (4) | O1—C9—C10—C5 | 170.49 (14) |
C2—C3'—C4—C3 | 38 (3) | C8—C9—C10—C4 | 177.50 (16) |
C3—C3'—C4—C10 | −101 (2) | O1—C9—C10—C4 | −8.1 (2) |
C42—C3'—C4—C10 | 103 (2) | C3—C4—C10—C5 | 154.83 (19) |
C2—C3'—C4—C10 | −63 (4) | C41—C4—C10—C5 | 40.1 (3) |
C3—C3'—C4—C41 | 70 (5) | C42—C4—C10—C5 | −87.0 (3) |
C42—C3'—C4—C41 | −86 (4) | C3'—C4—C10—C5 | −146 (3) |
C2—C3'—C4—C41 | 108 (4) | C3—C4—C10—C9 | −26.7 (2) |
C3—C3'—C4—C42 | 156 (4) | C41—C4—C10—C9 | −141.4 (2) |
C2—C3'—C4—C42 | −166 (6) | C42—C4—C10—C9 | 91.5 (2) |
C3—C3'—C42—C4 | −22 (4) | C3'—C4—C10—C9 | 32 (3) |
(cum250) 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin
top
Crystal data top
C14H18O3 | V = 1268.5 (5) Å3 |
Mr = 234.28 | Z = 4 |
P21/c, monoclinic | F(000) = 504 |
a = 9.729 (1) Å | Dx = 1.227 Mg m−3 |
b = 6.868 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 19.047 (4) Å | µ = 0.09 mm−1 |
α = 90° | T = 250 K |
β = 94.67 (2)° | , colourlees |
γ = 90° | 0.30 × 0.25 × 0.12 mm |
Data collection top
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 29.5°, θmin = 3.2° |
8379 measured reflections | h = −13→12 |
3238 independent reflections | k = −4→9 |
1232 reflections with I > 2σ(I) | l = −25→25 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.166 | w = 1/[σ2(Fo2) + (0.0604P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.014 |
3238 reflections | Δρmax = 0.21 e Å−3 |
230 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0014 (13) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.10337 (16) | 0.2341 (2) | 0.24764 (9) | 0.0475 (5) | |
O2 | −0.11512 (19) | 0.2351 (3) | 0.26179 (13) | 0.0789 (8) | |
O6 | 0.65065 (18) | 0.2614 (2) | 0.33858 (11) | 0.0497 (5) | |
H6 | 0.716 (5) | 0.257 (5) | 0.307 (2) | 0.121 (16)* | |
C2 | −0.0005 (3) | 0.2708 (4) | 0.28712 (16) | 0.0503 (8) | |
C3 | 0.0382 (3) | 0.3624 (6) | 0.35585 (18) | 0.0581 (12) | 0.965 (6) |
H3A | −0.044 (3) | 0.361 (4) | 0.3830 (14) | 0.067 (9)* | |
H3B | 0.072 (3) | 0.508 (4) | 0.3479 (15) | 0.069 (9)* | |
C3' | 0.034 (9) | 0.181 (15) | 0.356 (5) | 0.060* | 0.035 (6) |
C4 | 0.1637 (3) | 0.2690 (4) | 0.39565 (14) | 0.0514 (8) | |
C41 | 0.1958 (6) | 0.4032 (11) | 0.4601 (3) | 0.110 (2) | |
H41A | 0.107 (4) | 0.410 (5) | 0.4806 (18) | 0.097 (11)* | |
H41B | 0.205 (9) | 0.516 (13) | 0.437 (5) | 0.35 (6)* | |
H41C | 0.267 (5) | 0.349 (7) | 0.491 (2) | 0.141 (18)* | |
C42 | 0.1282 (5) | 0.0578 (8) | 0.4160 (3) | 0.1006 (18) | |
H42A | 0.210 (4) | 0.032 (6) | 0.452 (2) | 0.143 (19)* | |
H42B | 0.104 (7) | −0.026 (9) | 0.369 (3) | 0.23 (3)* | |
H42C | 0.060 (3) | 0.069 (4) | 0.4481 (17) | 0.091 (12)* | |
C5 | 0.4202 (2) | 0.2586 (3) | 0.36638 (12) | 0.0369 (6) | |
C51 | 0.4813 (4) | 0.2404 (6) | 0.44203 (17) | 0.0610 (9) | |
H51A | 0.418 (3) | 0.152 (5) | 0.4703 (17) | 0.093 (12)* | |
H51B | 0.488 (3) | 0.369 (5) | 0.4617 (17) | 0.098 (12)* | |
H51C | 0.562 (4) | 0.163 (4) | 0.4424 (16) | 0.092 (12)* | |
C6 | 0.5145 (2) | 0.2622 (3) | 0.31473 (13) | 0.0331 (6) | |
C7 | 0.4730 (2) | 0.2649 (3) | 0.24281 (12) | 0.0332 (6) | |
C71 | 0.5802 (3) | 0.2670 (5) | 0.19073 (18) | 0.0456 (7) | |
H71A | 0.538 (4) | 0.289 (5) | 0.145 (2) | 0.107 (14)* | |
H71B | 0.636 (3) | 0.152 (4) | 0.1953 (14) | 0.071 (9)* | |
H71C | 0.642 (3) | 0.375 (4) | 0.1945 (15) | 0.083 (10)* | |
C8 | 0.3331 (2) | 0.2609 (3) | 0.22197 (12) | 0.0320 (6) | |
C81 | 0.2806 (3) | 0.2580 (5) | 0.14588 (15) | 0.0474 (7) | |
H81A | 0.306 (3) | 0.137 (5) | 0.1193 (18) | 0.111 (13)* | |
H81B | 0.312 (3) | 0.353 (4) | 0.1171 (16) | 0.079 (11)* | |
H81C | 0.186 (5) | 0.262 (5) | 0.144 (2) | 0.139 (17)* | |
C9 | 0.2419 (2) | 0.2581 (3) | 0.27421 (12) | 0.0345 (6) | |
C10 | 0.2794 (2) | 0.2633 (3) | 0.34583 (12) | 0.0353 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0250 (9) | 0.0686 (13) | 0.0493 (11) | −0.0039 (9) | 0.0048 (8) | −0.0062 (10) |
O2 | 0.0281 (11) | 0.1108 (19) | 0.0981 (18) | −0.0059 (12) | 0.0068 (11) | −0.0159 (14) |
O6 | 0.0280 (10) | 0.0562 (12) | 0.0634 (13) | 0.0004 (9) | −0.0047 (9) | −0.0030 (11) |
C2 | 0.0297 (14) | 0.0606 (19) | 0.0613 (19) | 0.0029 (15) | 0.0081 (14) | 0.0035 (17) |
C3 | 0.036 | 0.083 (3) | 0.057 (2) | 0.0139 (18) | 0.0166 (16) | −0.002 (2) |
C4 | 0.0441 (16) | 0.070 (2) | 0.0422 (16) | 0.0123 (15) | 0.0164 (13) | 0.0102 (16) |
C41 | 0.077 (3) | 0.199 (6) | 0.054 (3) | 0.058 (3) | 0.010 (2) | −0.032 (3) |
C42 | 0.075 (3) | 0.120 (4) | 0.114 (4) | 0.011 (3) | 0.049 (3) | 0.065 (4) |
C5 | 0.0388 (14) | 0.0339 (14) | 0.0374 (14) | 0.0011 (12) | −0.0007 (12) | −0.0020 (13) |
C51 | 0.0543 (19) | 0.078 (3) | 0.0486 (19) | 0.016 (2) | −0.0067 (15) | −0.002 (2) |
C6 | 0.0250 (12) | 0.0279 (13) | 0.0456 (15) | 0.0015 (11) | −0.0010 (11) | −0.0046 (12) |
C7 | 0.0323 (13) | 0.0281 (13) | 0.0404 (14) | 0.0007 (11) | 0.0095 (11) | −0.0011 (12) |
C71 | 0.0323 (14) | 0.0461 (19) | 0.060 (2) | 0.0022 (15) | 0.0158 (14) | 0.0045 (18) |
C8 | 0.0311 (12) | 0.0304 (13) | 0.0345 (13) | −0.0007 (11) | 0.0022 (10) | 0.0000 (12) |
C81 | 0.0455 (18) | 0.060 (2) | 0.0364 (16) | −0.0066 (18) | 0.0031 (13) | −0.0011 (18) |
C9 | 0.0254 (12) | 0.0366 (14) | 0.0412 (15) | 0.0006 (12) | 0.0012 (10) | 0.0002 (13) |
C10 | 0.0332 (13) | 0.0367 (14) | 0.0366 (14) | 0.0016 (12) | 0.0064 (11) | 0.0022 (13) |
Geometric parameters (Å, º) top
O1—C2 | 1.332 (3) | C42—H42A | 1.02 (4) |
O1—C9 | 1.410 (3) | C42—H42B | 1.07 (6) |
O2—C2 | 1.204 (3) | C42—H42C | 0.94 (3) |
O6—C6 | 1.365 (3) | C5—C10 | 1.394 (3) |
O6—H6 | 0.91 (4) | C5—C6 | 1.399 (3) |
C2—C3 | 1.473 (4) | C5—C51 | 1.518 (4) |
C2—C3' | 1.46 (10) | C51—H51A | 1.04 (3) |
C3—C3' | 1.25 (10) | C51—H51B | 0.96 (3) |
C3—C4 | 1.525 (4) | C51—H51C | 0.95 (3) |
C3—H3A | 0.98 (3) | C6—C7 | 1.396 (3) |
C3—H3B | 1.06 (3) | C7—C8 | 1.387 (3) |
C3'—C4 | 1.54 (10) | C7—C71 | 1.496 (3) |
C3'—C42 | 1.64 (10) | C71—H71A | 0.95 (4) |
C3'—H3A | 1.56 (10) | C71—H71B | 0.96 (3) |
C3'—H42B | 1.59 (11) | C71—H71C | 0.95 (3) |
C4—C10 | 1.531 (3) | C8—C9 | 1.386 (3) |
C4—C41 | 1.547 (5) | C8—C81 | 1.497 (4) |
C4—C42 | 1.548 (5) | C81—H81A | 1.01 (4) |
C41—H41A | 0.97 (4) | C81—H81B | 0.92 (3) |
C41—H41B | 0.90 (9) | C81—H81C | 0.92 (5) |
C41—H41C | 0.95 (5) | C9—C10 | 1.384 (3) |
| | | |
C2—O1—C9 | 121.5 (2) | H41B—C41—H41C | 123 (6) |
C6—O6—H6 | 120 (3) | C4—C42—C3' | 58 (3) |
O2—C2—O1 | 117.1 (3) | C4—C42—H42A | 99 (2) |
O2—C2—C3 | 127.2 (3) | C3'—C42—H42A | 156 (4) |
O1—C2—C3 | 115.6 (2) | C4—C42—H42B | 110 (3) |
O2—C2—C3' | 114 (4) | C3'—C42—H42B | 68 (4) |
O1—C2—C3' | 107 (4) | H42A—C42—H42B | 125 (4) |
C3—C2—C3' | 50 (4) | C4—C42—H42C | 106 (2) |
C3'—C3—C2 | 64 (5) | C3'—C42—H42C | 92 (4) |
C3'—C3—C4 | 67 (4) | H42A—C42—H42C | 98 (3) |
C2—C3—C4 | 113.5 (3) | H42B—C42—H42C | 118 (4) |
C3'—C3—H3A | 88 (4) | C10—C5—C6 | 119.2 (2) |
C2—C3—H3A | 107.8 (15) | C10—C5—C51 | 124.6 (2) |
C4—C3—H3A | 112.7 (16) | C6—C5—C51 | 116.1 (2) |
C3'—C3—H3B | 161 (4) | C5—C51—H51A | 109.7 (17) |
C2—C3—H3B | 109.4 (16) | C5—C51—H51B | 108 (2) |
C4—C3—H3B | 102.8 (15) | H51A—C51—H51B | 111 (3) |
H3A—C3—H3B | 111 (2) | C5—C51—H51C | 108.3 (19) |
C3—C3'—C2 | 65 (5) | H51A—C51—H51C | 101 (3) |
C3—C3'—C4 | 65 (4) | H51B—C51—H51C | 119 (3) |
C2—C3'—C4 | 113 (6) | O6—C6—C7 | 121.4 (2) |
C3—C3'—C42 | 120 (7) | O6—C6—C5 | 116.1 (2) |
C2—C3'—C42 | 156 (7) | C7—C6—C5 | 122.4 (2) |
C4—C3'—C42 | 58 (3) | C8—C7—C6 | 118.6 (2) |
C3—C3'—H3A | 39 (3) | C8—C7—C71 | 122.1 (2) |
C2—C3'—H3A | 83 (5) | C6—C7—C71 | 119.3 (2) |
C4—C3'—H3A | 86 (5) | C7—C71—H71A | 110 (2) |
C42—C3'—H3A | 116 (6) | C7—C71—H71B | 110.6 (16) |
C3—C3'—H42B | 152 (8) | H71A—C71—H71B | 114 (3) |
C2—C3'—H42B | 126 (7) | C7—C71—H71C | 115.3 (18) |
C4—C3'—H42B | 87 (6) | H71A—C71—H71C | 100 (3) |
C42—C3'—H42B | 39 (3) | H71B—C71—H71C | 106 (3) |
H3A—C3'—H42B | 151 (8) | C9—C8—C7 | 117.8 (2) |
C3—C4—C10 | 107.6 (2) | C9—C8—C81 | 120.4 (2) |
C3—C4—C3' | 48 (4) | C7—C8—C81 | 121.8 (2) |
C10—C4—C3' | 108 (3) | C8—C81—H81A | 114.7 (19) |
C3—C4—C41 | 104.3 (3) | C8—C81—H81B | 117.4 (19) |
C10—C4—C41 | 113.3 (3) | H81A—C81—H81B | 100 (3) |
C3'—C4—C41 | 137 (4) | C8—C81—H81C | 108 (3) |
C3—C4—C42 | 109.4 (3) | H81A—C81—H81C | 106 (3) |
C10—C4—C42 | 108.8 (3) | H81B—C81—H81C | 110 (3) |
C3'—C4—C42 | 64 (4) | C10—C9—C8 | 125.0 (2) |
C41—C4—C42 | 113.2 (4) | C10—C9—O1 | 121.7 (2) |
C4—C41—H41A | 103 (2) | C8—C9—O1 | 113.1 (2) |
C4—C41—H41B | 98 (6) | C9—C10—C5 | 116.8 (2) |
H41A—C41—H41B | 106 (6) | C9—C10—C4 | 117.6 (2) |
C4—C41—H41C | 110 (3) | C5—C10—C4 | 125.6 (2) |
H41A—C41—H41C | 114 (3) | | |
| | | |
C9—O1—C2—O2 | −175.5 (2) | C10—C4—C42—C3' | −101 (4) |
C9—O1—C2—C3 | 8.0 (4) | C41—C4—C42—C3' | 132 (4) |
C9—O1—C2—C3' | −46 (4) | C3—C3'—C42—C4 | −22 (5) |
O2—C2—C3—C3' | 92 (5) | C2—C3'—C42—C4 | 74 (17) |
O1—C2—C3—C3' | −92 (5) | C10—C5—C6—O6 | 178.7 (2) |
O2—C2—C3—C4 | 138.9 (3) | C51—C5—C6—O6 | −4.0 (3) |
O1—C2—C3—C4 | −45.0 (4) | C10—C5—C6—C7 | −1.8 (3) |
C3'—C2—C3—C4 | 47 (5) | C51—C5—C6—C7 | 175.5 (3) |
C4—C3—C3'—C2 | −133 (3) | O6—C6—C7—C8 | 178.5 (2) |
C2—C3—C3'—C4 | 133 (3) | C5—C6—C7—C8 | −1.0 (3) |
C2—C3—C3'—C42 | 154 (8) | O6—C6—C7—C71 | 0.0 (3) |
C4—C3—C3'—C42 | 21 (4) | C5—C6—C7—C71 | −179.5 (2) |
O2—C2—C3'—C3 | −119 (3) | C6—C7—C8—C9 | 1.2 (3) |
O1—C2—C3'—C3 | 109 (3) | C71—C7—C8—C9 | 179.6 (2) |
O2—C2—C3'—C4 | −165 (4) | C6—C7—C8—C81 | −178.3 (3) |
O1—C2—C3'—C4 | 63 (6) | C71—C7—C8—C81 | 0.1 (4) |
C3—C2—C3'—C4 | −46 (4) | C7—C8—C9—C10 | 1.5 (4) |
O2—C2—C3'—C42 | 132 (16) | C81—C8—C9—C10 | −179.0 (3) |
O1—C2—C3'—C42 | 1 (19) | C7—C8—C9—O1 | −173.9 (2) |
C3—C2—C3'—C42 | −108 (19) | C81—C8—C9—O1 | 5.6 (3) |
C3'—C3—C4—C10 | 98 (5) | C2—O1—C9—C10 | 19.6 (3) |
C2—C3—C4—C10 | 52.3 (4) | C2—O1—C9—C8 | −164.8 (2) |
C2—C3—C4—C3' | −46 (5) | C8—C9—C10—C5 | −4.3 (4) |
C3'—C3—C4—C41 | −141 (5) | O1—C9—C10—C5 | 170.8 (2) |
C2—C3—C4—C41 | 172.9 (4) | C8—C9—C10—C4 | 177.1 (2) |
C3'—C3—C4—C42 | −20 (5) | O1—C9—C10—C4 | −7.8 (3) |
C2—C3—C4—C42 | −65.7 (4) | C6—C5—C10—C9 | 4.3 (3) |
C2—C3'—C4—C3 | 46 (5) | C51—C5—C10—C9 | −172.8 (3) |
C42—C3'—C4—C3 | −159 (5) | C6—C5—C10—C4 | −177.3 (2) |
C3—C3'—C4—C10 | −98 (3) | C51—C5—C10—C4 | 5.7 (4) |
C2—C3'—C4—C10 | −52 (7) | C3—C4—C10—C9 | −26.6 (3) |
C42—C3'—C4—C10 | 102.8 (19) | C3'—C4—C10—C9 | 24 (4) |
C3—C3'—C4—C41 | 62 (6) | C41—C4—C10—C9 | −141.3 (4) |
C2—C3'—C4—C41 | 108 (6) | C42—C4—C10—C9 | 91.8 (3) |
C42—C3'—C4—C41 | −97 (4) | C3—C4—C10—C5 | 154.9 (3) |
C3—C3'—C4—C42 | 159 (5) | C3'—C4—C10—C5 | −155 (4) |
C2—C3'—C4—C42 | −155 (7) | C41—C4—C10—C5 | 40.2 (4) |
C3—C4—C42—C3' | 16 (4) | C42—C4—C10—C5 | −86.6 (4) |
(cum278) 6-hydroxy-4,4,5,6,7-pentamethyl-3,4-dihydrocoumarin
top
Crystal data top
C14H18O3 | V = 1276.2 (6) Å3 |
Mr = 234.28 | Z = 4 |
P21/c, monoclinic | F(000) = 504 |
a = 9.739 (2) Å | Dx = 1.219 Mg m−3 |
b = 6.895 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 19.066 (5) Å | µ = 0.09 mm−1 |
α = 90° | T = 278 K |
β = 94.57 (3)° | , colourlees |
γ = 90° | 0.30 × 0.25 × 0.12 mm |
Data collection top
Radiation source: fine-focus sealed tube | Rint = 0.055 |
Graphite monochromator | θmax = 29.4°, θmin = 3.6° |
7992 measured reflections | h = −13→12 |
3226 independent reflections | k = −4→9 |
892 reflections with I > 2σ(I) | l = −25→25 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.058 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.128 | w = 1/[σ2(Fo2) + (0.0425P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.82 | (Δ/σ)max = 1.707 |
3226 reflections | Δρmax = 0.15 e Å−3 |
262 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0055 (10) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.10405 (15) | 0.2359 (3) | 0.24767 (9) | 0.0579 (5) | |
O2 | −0.11485 (19) | 0.2371 (3) | 0.26196 (12) | 0.0948 (8) | |
O6 | 0.65040 (17) | 0.2599 (3) | 0.33850 (11) | 0.0577 (6) | |
H6 | 0.711 (3) | 0.249 (5) | 0.3045 (18) | 0.116 (14)* | |
C2 | −0.0007 (3) | 0.2677 (5) | 0.28746 (16) | 0.0613 (8) | |
C3 | 0.0400 (4) | 0.3604 (7) | 0.3562 (2) | 0.0689 (13) | 0.904 (3) |
H3A | −0.0401 | 0.354 (4) | 0.3809 (15) | 0.070 (10)* | 0.904 (3) |
H3B | 0.073 (3) | 0.516 (4) | 0.3477 (14) | 0.070 (9)* | 0.904 (3) |
C3' | 0.028 (3) | 0.162 (5) | 0.3580 (17) | 0.041* | 0.096 (3) |
H3C | 0.0578 | 0.0174 | 0.3454 | 0.09 (11)* | 0.096 (3) |
H3D | −0.0447 | 0.1490 | 0.3837 | 0.09 (11)* | 0.096 (3) |
C4 | 0.1643 (3) | 0.2654 (5) | 0.39573 (14) | 0.0607 (8) | |
C41 | 0.1948 (5) | 0.4001 (12) | 0.4601 (3) | 0.115 (2) | 0.904 (3) |
H41A | 0.2163 | 0.5238 | 0.4447 | 0.19 (11)* | 0.904 (3) |
H41B | 0.2713 | 0.3458 | 0.4889 | 0.144 (18)* | 0.904 (3) |
H41C | 0.1157 | 0.4023 | 0.4872 | 0.130 (15)* | 0.904 (3) |
C41' | 0.208 (7) | 0.124 (6) | 0.475 (3) | 0.094* | 0.096 (3) |
H41D | 0.1193 | 0.1182 | 0.4916 | 0.11 (9)* | 0.096 (3) |
H41E | 0.2778 | 0.1458 | 0.4875 | 0.2 (3)* | 0.096 (3) |
H41F | 0.2000 | −0.0168 | 0.4435 | 0.04 (8)* | 0.096 (3) |
C42 | 0.1296 (6) | 0.0606 (9) | 0.4172 (4) | 0.114 (2) | 0.904 (3) |
H42A | 0.0573 | 0.0649 | 0.4490 | 0.092 (11)* | 0.904 (3) |
H42B | 0.2094 | 0.0021 | 0.4408 | 0.14 (3)* | 0.904 (3) |
H42C | 0.0996 | −0.0124 | 0.3768 | 0.19 (3)* | 0.904 (3) |
C42' | 0.122 (6) | 0.476 (6) | 0.415 (3) | 0.089* | 0.096 (3) |
H42D | 0.0608 | 0.4451 | 0.4486 | 0.13 (15)* | 0.096 (3) |
H42E | 0.1057 | 0.5270 | 0.3775 | 2 (5)* | 0.096 (3) |
H42F | 0.2138 | 0.5056 | 0.4419 | 0.8 (13)* | 0.096 (3) |
C5 | 0.4200 (2) | 0.2569 (4) | 0.36607 (12) | 0.0426 (6) | |
C51 | 0.4805 (5) | 0.2412 (9) | 0.44131 (18) | 0.0708 (10) | |
H51A | 0.414 (5) | 0.177 (8) | 0.468 (3) | 0.027 (16)* | 0.50 |
H51B | 0.534 (8) | 0.377 (11) | 0.454 (3) | 0.08 (2)* | 0.50 |
H51C | 0.572 (6) | 0.125 (9) | 0.440 (2) | 0.06 (2)* | 0.50 |
H51D | 0.581 (7) | 0.233 (15) | 0.442 (3) | 0.08 (2)* | 0.50 |
H51E | 0.448 (13) | 0.085 (13) | 0.460 (5) | 0.19 (5)* | 0.50 |
H51F | 0.461 (6) | 0.372 (9) | 0.472 (3) | 0.07 (2)* | 0.50 |
C6 | 0.5133 (2) | 0.2595 (4) | 0.31427 (13) | 0.0395 (6) | |
C7 | 0.4732 (2) | 0.2633 (3) | 0.24280 (12) | 0.0367 (6) | |
C71 | 0.5801 (3) | 0.2647 (7) | 0.1909 (2) | 0.0528 (9) | |
H71A | 0.712 (10) | 0.246 (16) | 0.215 (5) | 0.20 (4)* | 0.50 |
H71B | 0.572 (8) | 0.192 (10) | 0.156 (4) | 0.08 (3)* | 0.50 |
H71C | 0.520 (5) | 0.272 (9) | 0.140 (3) | 0.040 (15)* | 0.50 |
H71D | 0.591 (9) | 0.366 (11) | 0.146 (4) | 0.14 (3)* | 0.50 |
H71E | 0.637 (5) | 0.150 (6) | 0.194 (3) | 0.013 (12)* | 0.50 |
H71F | 0.647 (4) | 0.372 (5) | 0.201 (2) | 0.000 (10)* | 0.50 |
C8 | 0.3330 (2) | 0.2588 (4) | 0.22223 (12) | 0.0366 (6) | |
C81 | 0.2806 (4) | 0.2590 (7) | 0.14611 (16) | 0.0525 (8) | |
H81A | 0.368 (7) | 0.343 (10) | 0.103 (3) | 0.11 (2)* | 0.50 |
H81B | 0.163 (4) | 0.310 (5) | 0.148 (2) | 0.031 (12)* | 0.50 |
H81C | 0.308 (6) | 0.103 (8) | 0.124 (3) | 0.06 (2)* | 0.50 |
H81D | 0.204 (5) | 0.176 (6) | 0.137 (2) | 0.028 (15)* | 0.50 |
H81E | 0.277 (5) | 0.377 (6) | 0.128 (2) | 0.032 (16)* | 0.50 |
H81F | 0.334 (4) | 0.191 (7) | 0.119 (2) | 0.005 (13)* | 0.50 |
C9 | 0.2421 (2) | 0.2565 (4) | 0.27452 (13) | 0.0401 (6) | |
C10 | 0.2794 (2) | 0.2616 (4) | 0.34575 (12) | 0.0403 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0274 (9) | 0.0871 (14) | 0.0594 (12) | −0.0058 (12) | 0.0040 (9) | −0.0042 (13) |
O2 | 0.0337 (12) | 0.135 (2) | 0.1159 (18) | −0.0065 (15) | 0.0062 (12) | −0.0153 (16) |
O6 | 0.0336 (10) | 0.0684 (13) | 0.0696 (14) | 0.0014 (12) | −0.0057 (10) | −0.0038 (13) |
C2 | 0.0356 (16) | 0.074 (2) | 0.075 (2) | 0.003 (2) | 0.0113 (16) | 0.006 (2) |
C3 | 0.041 (2) | 0.102 (4) | 0.066 (3) | 0.012 (2) | 0.022 (2) | −0.004 (3) |
C4 | 0.0504 (18) | 0.083 (2) | 0.0507 (18) | 0.014 (2) | 0.0187 (15) | 0.017 (2) |
C41 | 0.090 (4) | 0.203 (8) | 0.053 (3) | 0.061 (4) | 0.010 (3) | −0.030 (3) |
C42 | 0.083 (3) | 0.137 (4) | 0.131 (5) | 0.019 (3) | 0.059 (4) | 0.082 (5) |
C5 | 0.0396 (14) | 0.0463 (16) | 0.0411 (15) | 0.0000 (18) | −0.0012 (13) | −0.0005 (19) |
C51 | 0.058 (2) | 0.095 (3) | 0.057 (2) | 0.006 (3) | −0.007 (2) | −0.006 (3) |
C6 | 0.0288 (13) | 0.0373 (15) | 0.0516 (17) | −0.0006 (17) | −0.0029 (12) | −0.0062 (18) |
C7 | 0.0370 (14) | 0.0306 (13) | 0.0434 (16) | 0.0006 (16) | 0.0092 (12) | −0.0031 (16) |
C71 | 0.0401 (18) | 0.055 (2) | 0.065 (2) | 0.001 (2) | 0.0158 (17) | −0.006 (3) |
C8 | 0.0370 (14) | 0.0317 (14) | 0.0407 (15) | −0.0009 (16) | 0.0018 (12) | −0.0004 (17) |
C81 | 0.051 (2) | 0.063 (3) | 0.045 (2) | −0.001 (3) | 0.0068 (16) | −0.009 (3) |
C9 | 0.0257 (13) | 0.0448 (15) | 0.0500 (17) | −0.0018 (16) | 0.0037 (11) | −0.0027 (19) |
C10 | 0.0376 (14) | 0.0446 (15) | 0.0392 (16) | −0.0002 (17) | 0.0070 (12) | 0.0023 (18) |
Geometric parameters (Å, º) top
O1—C2 | 1.337 (3) | C42—H41F | 0.975 (6) |
O1—C9 | 1.407 (2) | C42—H42A | 0.966 (5) |
O2—C2 | 1.196 (3) | C42—H42B | 0.955 (6) |
O6—C6 | 1.378 (3) | C42—H42C | 0.947 (9) |
O6—H6 | 0.92 (4) | C42'—H3B | 1.37 (5) |
C2—C3 | 1.484 (5) | C42'—H41A | 1.09 (6) |
C2—C3' | 1.54 (3) | C42'—H41C | 1.47 (5) |
C3—C3' | 1.38 (3) | C42'—H42D | 0.93 (5) |
C3—C4 | 1.522 (4) | C42'—H42E | 0.81 (6) |
C3—C42' | 1.55 (5) | C42'—H42F | 1.01 (6) |
C3—H3A | 0.944 (15) | C5—C10 | 1.393 (3) |
C3—H3B | 1.14 (3) | C5—C6 | 1.395 (3) |
C3—H42E | 1.361 (5) | C5—C51 | 1.511 (4) |
C3'—C42 | 1.60 (3) | C51—H51A | 0.96 (6) |
C3'—C4 | 1.62 (3) | C51—H51B | 1.09 (7) |
C3'—H3C | 1.07 (3) | C51—H51C | 1.20 (5) |
C3'—H3D | 0.90 (3) | C51—H51D | 0.97 (6) |
C3'—H42C | 1.42 (3) | C51—H51E | 1.18 (10) |
C4—C42 | 1.516 (5) | C51—H51F | 1.10 (6) |
C4—C10 | 1.528 (3) | C6—C7 | 1.387 (3) |
C4—C42' | 1.56 (4) | C7—C8 | 1.391 (3) |
C4—C41 | 1.549 (5) | C7—C71 | 1.493 (3) |
C4—C41' | 1.82 (5) | C71—H71A | 1.34 (10) |
C41—C42' | 1.19 (6) | C71—H71B | 0.83 (6) |
C41—C41' | 1.93 (4) | C71—H71C | 1.09 (5) |
C41—H41A | 0.932 (9) | C71—H71D | 1.11 (8) |
C41—H41B | 0.966 (5) | C71—H71E | 0.96 (4) |
C41—H41C | 0.960 (5) | C71—H71F | 1.00 (4) |
C41—H42D | 1.343 (5) | C8—C9 | 1.385 (3) |
C41—H42F | 0.834 (9) | C8—C81 | 1.499 (4) |
C41'—C42 | 1.36 (6) | C81—H81A | 1.36 (6) |
C41'—H41D | 0.94 (6) | C81—H81B | 1.20 (4) |
C41'—H41E | 0.72 (7) | C81—H81C | 1.19 (6) |
C41'—H41F | 1.14 (5) | C81—H81D | 0.95 (4) |
C41'—H42B | 1.06 (5) | C81—H81E | 0.89 (4) |
C42—H3C | 1.517 (9) | C81—H81F | 0.90 (5) |
C42—H41D | 1.484 (8) | C9—C10 | 1.378 (3) |
| | | |
C2—O1—C9 | 121.8 (2) | C3'—C42—H42A | 89.4 (12) |
C6—O6—H6 | 115 (2) | H3C—C42—H42A | 105.4 (6) |
O2—C2—O1 | 117.8 (3) | H41D—C42—H42A | 44.2 (4) |
O2—C2—C3 | 127.5 (3) | H41F—C42—H42A | 102.3 (5) |
O1—C2—C3 | 114.2 (3) | C41'—C42—H42B | 51.2 (19) |
O2—C2—C3' | 111.8 (12) | C4—C42—H42B | 109.3 (6) |
O1—C2—C3' | 108.9 (12) | C3'—C42—H42B | 161.7 (12) |
C3—C2—C3' | 54.1 (11) | H3C—C42—H42B | 129.9 (7) |
C3'—C3—C2 | 64.9 (14) | H41D—C42—H42B | 77.1 (5) |
C3'—C3—C4 | 67.9 (13) | H41F—C42—H42B | 9.99 (6) |
C2—C3—C4 | 113.4 (3) | H42A—C42—H42B | 108.9 (6) |
C3'—C3—C42' | 122 (2) | C41'—C42—H42C | 161 (2) |
C2—C3—C42' | 161.8 (18) | C4—C42—H42C | 109.6 (5) |
C4—C3—C42' | 61.1 (17) | C3'—C42—H42C | 61.6 (12) |
C3'—C3—H3A | 82 (2) | H3C—C42—H42C | 21.69 (19) |
C2—C3—H3A | 104.4 (16) | H41D—C42—H42C | 151.7 (4) |
C4—C3—H3A | 112.9 (16) | H41F—C42—H42C | 106.6 (6) |
C42'—C3—H3A | 93 (2) | H42A—C42—H42C | 109.5 (7) |
C3'—C3—H3B | 166 (2) | H42B—C42—H42C | 110.2 (6) |
C2—C3—H3B | 109.8 (14) | C41—C42'—C4 | 67 (2) |
C4—C3—H3B | 104.8 (13) | C41—C42'—C3 | 123 (3) |
C42'—C3—H3B | 58.9 (18) | C4—C42'—C3 | 58.6 (16) |
H3A—C3—H3B | 112 (2) | C41—C42'—H3B | 156 (4) |
C3'—C3—H42E | 150.7 (14) | C4—C42'—H3B | 93 (3) |
C2—C3—H42E | 135.5 (3) | C3—C42'—H3B | 45 (2) |
C4—C3—H42E | 83.0 (3) | C41—C42'—H41A | 48 (2) |
C42'—C3—H42E | 31.3 (18) | C4—C42'—H41A | 100 (3) |
H3A—C3—H42E | 106.1 (17) | C3—C42'—H41A | 154 (4) |
H3B—C3—H42E | 27.6 (13) | H3B—C42'—H41A | 130 (4) |
C3—C3'—C2 | 60.9 (14) | C41—C42'—H41C | 40.7 (18) |
C3—C3'—C42 | 114 (2) | C4—C42'—H41C | 86 (2) |
C2—C3'—C42 | 152 (2) | C3—C42'—H41C | 116 (3) |
C3—C3'—C4 | 60.3 (12) | H3B—C42'—H41C | 156 (5) |
C2—C3'—C4 | 105.3 (18) | H41A—C42'—H41C | 74 (3) |
C42—C3'—C4 | 56.1 (11) | C41—C42'—H42D | 78 (4) |
C3—C3'—H3C | 154 (3) | C4—C42'—H42D | 98 (3) |
C2—C3'—H3C | 106 (2) | C3—C42'—H42D | 93 (4) |
C42—C3'—H3C | 65.8 (17) | H3B—C42'—H42D | 120 (5) |
C4—C3'—H3C | 106 (2) | H41A—C42'—H42D | 106 (5) |
C3—C3'—H3D | 101 (3) | H41C—C42'—H42D | 37 (2) |
C2—C3'—H3D | 115 (3) | C41—C42'—H42E | 154 (6) |
C42—C3'—H3D | 93 (2) | C4—C42'—H42E | 103 (4) |
C4—C3'—H3D | 117 (3) | C3—C42'—H42E | 61 (3) |
H3C—C3'—H3D | 106 (3) | H3B—C42'—H42E | 16.2 (19) |
C3—C3'—H42C | 144 (2) | H41A—C42'—H42E | 115 (5) |
C2—C3'—H42C | 132 (2) | H41C—C42'—H42E | 165 (5) |
C42—C3'—H42C | 35.9 (8) | H42D—C42'—H42E | 128 (7) |
C4—C3'—H42C | 83.9 (16) | C41—C42'—H42F | 44 (2) |
H3C—C3'—H42C | 30.0 (9) | C4—C42'—H42F | 94 (3) |
H3D—C3'—H42C | 100 (3) | C3—C42'—H42F | 149 (4) |
C42—C4—C3 | 110.4 (4) | H3B—C42'—H42F | 131 (5) |
C42—C4—C10 | 110.1 (3) | H41A—C42'—H42F | 6.3 (4) |
C3—C4—C10 | 107.0 (2) | H41C—C42'—H42F | 73 (3) |
C42—C4—C42' | 137.1 (18) | H42D—C42'—H42F | 107 (5) |
C3—C4—C42' | 60 (2) | H42E—C42'—H42F | 118 (5) |
C10—C4—C42' | 112.6 (18) | C10—C5—C6 | 119.0 (2) |
C42—C4—C41 | 112.1 (5) | C10—C5—C51 | 124.5 (3) |
C3—C4—C41 | 103.2 (3) | C6—C5—C51 | 116.5 (3) |
C10—C4—C41 | 113.6 (3) | C5—C51—H51A | 108 (3) |
C42'—C4—C41 | 45 (2) | C5—C51—H51B | 107 (3) |
C42—C4—C3' | 61.2 (12) | H51A—C51—H51B | 128 (5) |
C3—C4—C3' | 51.7 (11) | C5—C51—H51C | 105 (2) |
C10—C4—C3' | 109.3 (11) | H51A—C51—H51C | 104 (4) |
C42'—C4—C3' | 107 (2) | H51B—C51—H51C | 104 (5) |
C41—C4—C3' | 135.5 (12) | C5—C51—H51D | 110 (3) |
C42—C4—C41' | 47.0 (18) | H51A—C51—H51D | 132 (5) |
C3—C4—C41' | 139.9 (19) | H51B—C51—H51D | 65 (4) |
C10—C4—C41' | 112.0 (17) | H51C—C51—H51D | 39 (5) |
C42'—C4—C41' | 110 (2) | C5—C51—H51E | 105 (4) |
C41—C4—C41' | 69.3 (16) | H51A—C51—H51E | 38 (6) |
C3'—C4—C41' | 105 (2) | H51B—C51—H51E | 148 (5) |
C42'—C41—C4 | 68 (2) | H51C—C51—H51E | 68 (5) |
C42'—C41—C41' | 125 (3) | H51D—C51—H51E | 104 (7) |
C4—C41—C41' | 61.9 (16) | C5—C51—H51F | 112 (3) |
C42'—C41—H41A | 60 (2) | H51A—C51—H51F | 86 (4) |
C4—C41—H41A | 109.4 (5) | H51B—C51—H51F | 44 (4) |
C41'—C41—H41A | 159.5 (16) | H51C—C51—H51F | 136 (4) |
C42'—C41—H41B | 166 (2) | H51D—C51—H51F | 105 (6) |
C4—C41—H41B | 108.0 (5) | H51E—C51—H51F | 121 (6) |
C41'—C41—H41B | 60 (2) | O6—C6—C7 | 121.2 (2) |
H41A—C41—H41B | 110.6 (7) | O6—C6—C5 | 115.6 (2) |
C42'—C41—H41C | 86 (2) | C7—C6—C5 | 123.2 (2) |
C4—C41—H41C | 108.9 (6) | C6—C7—C8 | 118.0 (2) |
C41'—C41—H41C | 89.1 (16) | C6—C7—C71 | 119.7 (3) |
H41A—C41—H41C | 111.4 (6) | C8—C7—C71 | 122.3 (2) |
H41B—C41—H41C | 108.4 (6) | C7—C71—H71A | 118 (4) |
C42'—C41—H42D | 43 (2) | C7—C71—H71B | 120 (5) |
C4—C41—H42D | 83.5 (3) | H71A—C71—H71B | 104 (7) |
C41'—C41—H42D | 108 (2) | C7—C71—H71C | 104 (3) |
H41A—C41—H42D | 88.7 (5) | H71A—C71—H71C | 138 (5) |
H41B—C41—H42D | 151.6 (7) | H71B—C71—H71C | 46 (6) |
H41C—C41—H42D | 43.44 (19) | C7—C71—H71D | 129 (4) |
C42'—C41—H42F | 57 (2) | H71A—C71—H71D | 100 (6) |
C4—C41—H42F | 103.1 (4) | H71B—C71—H71D | 77 (6) |
C41'—C41—H42F | 155.3 (15) | H71C—C71—H71D | 51 (4) |
H41A—C41—H42F | 6.32 (7) | C7—C71—H71E | 112 (2) |
H41B—C41—H42F | 112.8 (7) | H71A—C71—H71E | 51 (4) |
H41C—C41—H42F | 115.2 (6) | H71B—C71—H71E | 65 (5) |
H42D—C41—H42F | 88.6 (5) | H71C—C71—H71E | 111 (4) |
C42—C41'—C4 | 54.8 (18) | H71D—C71—H71E | 119 (5) |
C42—C41'—C41 | 100 (3) | C7—C71—H71F | 111 (2) |
C4—C41'—C41 | 48.8 (10) | H71A—C71—H71F | 54 (4) |
C42—C41'—H41D | 78 (5) | H71B—C71—H71F | 128 (5) |
C4—C41'—H41D | 98 (4) | H71C—C71—H71F | 116 (4) |
C41—C41'—H41D | 92 (3) | H71D—C71—H71F | 65 (4) |
C42—C41'—H41E | 142 (5) | H71E—C71—H71F | 104 (3) |
C4—C41'—H41E | 109 (4) | C9—C8—C7 | 117.8 (2) |
C41—C41'—H41E | 84 (4) | C9—C8—C81 | 120.6 (2) |
H41D—C41'—H41E | 139 (6) | C7—C8—C81 | 121.6 (2) |
C42—C41'—H41F | 45 (2) | C8—C81—H81A | 114 (3) |
C4—C41'—H41F | 91 (3) | C8—C81—H81B | 103.2 (19) |
C41—C41'—H41F | 140 (4) | H81A—C81—H81B | 122 (3) |
H41D—C41'—H41F | 97 (5) | C8—C81—H81C | 106 (2) |
H41E—C41'—H41F | 112 (5) | H81A—C81—H81C | 90 (4) |
C42—C41'—H42B | 44 (2) | H81B—C81—H81C | 121 (3) |
C4—C41'—H42B | 86 (3) | C8—C81—H81D | 112 (3) |
C41—C41'—H42B | 134 (3) | H81A—C81—H81D | 132 (4) |
H41D—C41'—H42B | 103 (6) | H81B—C81—H81D | 56 (3) |
H41E—C41'—H42B | 108 (5) | H81C—C81—H81D | 65 (3) |
H41F—C41'—H42B | 7.9 (4) | C8—C81—H81E | 113 (3) |
C41'—C42—C4 | 78.2 (18) | H81A—C81—H81E | 51 (3) |
C41'—C42—C3' | 135 (2) | H81B—C81—H81E | 74 (3) |
C4—C42—C3' | 62.7 (11) | H81C—C81—H81E | 134 (4) |
C41'—C42—H3C | 169 (2) | H81D—C81—H81E | 118 (4) |
C4—C42—H3C | 92.0 (3) | C8—C81—H81F | 113 (3) |
C3'—C42—H3C | 40.0 (12) | H81A—C81—H81F | 57 (3) |
C41'—C42—H41D | 38 (2) | H81B—C81—H81F | 140 (3) |
C4—C42—H41D | 92.4 (5) | H81C—C81—H81F | 34 (4) |
C3'—C42—H41D | 118.2 (12) | H81D—C81—H81F | 94 (4) |
H3C—C42—H41D | 148.7 (4) | H81E—C81—H81F | 105 (5) |
C41'—C42—H41F | 55.6 (18) | C10—C9—C8 | 125.2 (2) |
C4—C42—H41F | 119.0 (6) | C10—C9—O1 | 122.0 (2) |
C3'—C42—H41F | 166.0 (14) | C8—C9—O1 | 112.7 (2) |
H3C—C42—H41F | 127.7 (7) | C9—C10—C5 | 116.7 (2) |
H41D—C42—H41F | 75.8 (5) | C9—C10—C4 | 117.8 (2) |
C41'—C42—H42A | 83 (2) | C5—C10—C4 | 125.5 (2) |
C4—C42—H42A | 109.3 (5) | | |
| | | |
C9—O1—C2—O2 | −176.1 (3) | C42'—C41—C41'—C42 | 7 (5) |
C9—O1—C2—C3 | 10.9 (4) | C4—C41—C41'—C42 | −20.9 (16) |
C9—O1—C2—C3' | −47.4 (13) | C42'—C41—C41'—C4 | 28 (3) |
O2—C2—C3—C3' | 91.2 (15) | C41—C41'—C42—C4 | 19.2 (16) |
O1—C2—C3—C3' | −96.5 (15) | C4—C41'—C42—C3' | −30 (3) |
O2—C2—C3—C4 | 140.3 (4) | C41—C41'—C42—C3' | −11 (4) |
O1—C2—C3—C4 | −47.5 (4) | C3—C4—C42—C41' | −140 (2) |
C3'—C2—C3—C4 | 49.1 (14) | C10—C4—C42—C41' | 102 (2) |
O2—C2—C3—C42' | −151 (6) | C42'—C4—C42—C41' | −72 (4) |
O1—C2—C3—C42' | 21 (6) | C41—C4—C42—C41' | −26 (2) |
C3'—C2—C3—C42' | 118 (6) | C3'—C4—C42—C41' | −157 (3) |
C4—C3—C3'—C2 | −131.6 (10) | C3—C4—C42—C3' | 16.4 (14) |
C42'—C3—C3'—C2 | −161 (2) | C10—C4—C42—C3' | −101.6 (13) |
C2—C3—C3'—C42 | 149 (2) | C42'—C4—C42—C3' | 84 (3) |
C4—C3—C3'—C42 | 17.8 (14) | C41—C4—C42—C3' | 130.9 (13) |
C42'—C3—C3'—C42 | −12 (3) | C41'—C4—C42—C3' | 157 (3) |
C2—C3—C3'—C4 | 131.6 (10) | C3—C3'—C42—C41' | 15 (4) |
C42'—C3—C3'—C4 | −29 (2) | C2—C3'—C42—C41' | 87 (6) |
O2—C2—C3'—C3 | −121.4 (9) | C4—C3'—C42—C41' | 33 (4) |
O1—C2—C3'—C3 | 106.7 (10) | C3—C3'—C42—C4 | −18.6 (15) |
O2—C2—C3'—C42 | 152 (4) | C2—C3'—C42—C4 | 54 (4) |
O1—C2—C3'—C42 | 20 (5) | C41'—C41—C42'—C4 | −27 (3) |
C3—C2—C3'—C42 | −86 (5) | C4—C41—C42'—C3 | 19 (3) |
O2—C2—C3'—C4 | −163.7 (11) | C41'—C41—C42'—C3 | −8 (6) |
O1—C2—C3'—C4 | 64.3 (18) | C42—C4—C42'—C41 | 73 (3) |
C3—C2—C3'—C4 | −42.4 (10) | C3—C4—C42'—C41 | 161 (3) |
C3'—C3—C4—C42 | −18.3 (15) | C10—C4—C42'—C41 | −101.4 (19) |
C2—C3—C4—C42 | −65.9 (5) | C3'—C4—C42'—C41 | 138.5 (19) |
C42'—C3—C4—C42 | 133 (2) | C41'—C4—C42'—C41 | 25 (3) |
C3'—C3—C4—C10 | 101.4 (15) | C42—C4—C42'—C3 | −89 (3) |
C2—C3—C4—C10 | 53.9 (4) | C10—C4—C42'—C3 | 97.3 (13) |
C42'—C3—C4—C10 | −107 (2) | C41—C4—C42'—C3 | −161 (3) |
C3'—C3—C4—C42' | −152 (2) | C3'—C4—C42'—C3 | −22.8 (19) |
C2—C3—C4—C42' | 161 (2) | C41'—C4—C42'—C3 | −137 (2) |
C3'—C3—C4—C41 | −138.4 (15) | C3'—C3—C42'—C41 | 11 (5) |
C2—C3—C4—C41 | 174.0 (4) | C2—C3—C42'—C41 | −98 (6) |
C42'—C3—C4—C41 | 13 (2) | C4—C3—C42'—C41 | −21 (3) |
C2—C3—C4—C3' | −47.6 (14) | C3'—C3—C42'—C4 | 31 (3) |
C42'—C3—C4—C3' | 152 (2) | C2—C3—C42'—C4 | −77 (6) |
C3'—C3—C4—C41' | −65 (3) | C10—C5—C6—O6 | 178.3 (2) |
C2—C3—C4—C41' | −112 (3) | C51—C5—C6—O6 | −4.0 (4) |
C42'—C3—C4—C41' | 87 (3) | C10—C5—C6—C7 | −1.1 (4) |
C3—C3'—C4—C42 | 160.3 (16) | C51—C5—C6—C7 | 176.6 (3) |
C2—C3'—C4—C42 | −157 (2) | O6—C6—C7—C8 | 178.8 (2) |
C2—C3'—C4—C3 | 42.7 (11) | C5—C6—C7—C8 | −1.8 (4) |
C42—C3'—C4—C3 | −160.3 (16) | O6—C6—C7—C71 | 1.0 (4) |
C3—C3'—C4—C10 | −96.8 (10) | C5—C6—C7—C71 | −179.7 (3) |
C2—C3'—C4—C10 | −54.1 (19) | C6—C7—C8—C9 | 1.8 (4) |
C42—C3'—C4—C10 | 102.8 (8) | C71—C7—C8—C9 | 179.6 (3) |
C3—C3'—C4—C42' | 25 (2) | C6—C7—C8—C81 | −178.9 (3) |
C2—C3'—C4—C42' | 68 (3) | C71—C7—C8—C81 | −1.2 (5) |
C42—C3'—C4—C42' | −135 (2) | C7—C8—C9—C10 | 1.2 (4) |
C3—C3'—C4—C41 | 67.3 (19) | C81—C8—C9—C10 | −178.1 (3) |
C2—C3'—C4—C41 | 109.9 (17) | C7—C8—C9—O1 | −175.1 (2) |
C42—C3'—C4—C41 | −93.1 (15) | C81—C8—C9—O1 | 5.7 (4) |
C3—C3'—C4—C41' | 142.9 (17) | C2—O1—C9—C10 | 16.8 (4) |
C2—C3'—C4—C41' | −174.5 (19) | C2—O1—C9—C8 | −166.8 (3) |
C42—C3'—C4—C41' | −17.5 (18) | C8—C9—C10—C5 | −4.1 (4) |
C42—C4—C41—C42' | −135 (3) | O1—C9—C10—C5 | 171.8 (2) |
C3—C4—C41—C42' | −17 (3) | C8—C9—C10—C4 | 177.8 (3) |
C10—C4—C41—C42' | 99 (3) | O1—C9—C10—C4 | −6.2 (4) |
C3'—C4—C41—C42' | −65 (3) | C6—C5—C10—C9 | 3.9 (4) |
C41'—C4—C41—C42' | −155 (3) | C51—C5—C10—C9 | −173.6 (4) |
C42—C4—C41—C41' | 20 (2) | C6—C5—C10—C4 | −178.2 (3) |
C3—C4—C41—C41' | 139 (2) | C51—C5—C10—C4 | 4.3 (5) |
C10—C4—C41—C41' | −106 (2) | C42—C4—C10—C9 | 92.5 (4) |
C42'—C4—C41—C41' | 155 (3) | C3—C4—C10—C9 | −27.6 (4) |
C3'—C4—C41—C41' | 91 (3) | C42'—C4—C10—C9 | −92 (2) |
C3—C4—C41'—C42 | 68 (2) | C41—C4—C10—C9 | −140.8 (4) |
C10—C4—C41'—C42 | −97.4 (19) | C3'—C4—C10—C9 | 27.0 (13) |
C42'—C4—C41'—C42 | 136 (2) | C41'—C4—C10—C9 | 143 (2) |
C41—C4—C41'—C42 | 155 (2) | C42—C4—C10—C5 | −85.4 (5) |
C3'—C4—C41'—C42 | 21 (2) | C3—C4—C10—C5 | 154.6 (3) |
C42—C4—C41'—C41 | −155 (2) | C42'—C4—C10—C5 | 90 (2) |
C3—C4—C41'—C41 | −86 (3) | C41—C4—C10—C5 | 41.3 (5) |
C10—C4—C41'—C41 | 108.0 (7) | C3'—C4—C10—C5 | −150.8 (13) |
C42'—C4—C41'—C41 | −18 (3) | C41'—C4—C10—C5 | −35 (2) |
C3'—C4—C41'—C41 | −133.5 (13) | | |
(cum285) 6-hydrohy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin
top
Crystal data top
C14H18O3 | V = 1291.7 (10) Å3 |
Mr = 234.28 | Z = 4 |
P21/c, monoclinic | F(000) = 504 |
a = 9.768 (6) Å | Dx = 1.205 Mg m−3 |
b = 6.933 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 19.130 (4) Å | µ = 0.08 mm−1 |
α = 90° | T = 285 K |
β = 94.39 (4)° | , colourlees |
γ = 90° | 0.44 × 0.38 × 0.12 mm |
Data collection top
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 29.6°, θmin = 3.7° |
7944 measured reflections | h = −6→13 |
3313 independent reflections | k = −9→9 |
1715 reflections with I > 2σ(I) | l = −26→25 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.064 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.225 | w = 1/[σ2(Fo2) + (0.1297P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 1.085 |
3313 reflections | Δρmax = 0.35 e Å−3 |
275 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.002 (3) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.10328 (12) | 0.23771 (18) | 0.24761 (7) | 0.0593 (4) | |
O2 | −0.11509 (14) | 0.2375 (2) | 0.26193 (12) | 0.0963 (7) | |
O6 | 0.65005 (13) | 0.25892 (16) | 0.33843 (9) | 0.0588 (4) | |
H6 | 0.715 (3) | 0.247 (3) | 0.3034 (17) | 0.105 (10)* | |
C2 | −0.00100 (19) | 0.2660 (3) | 0.28728 (13) | 0.0647 (6) | |
C3 | 0.0379 (2) | 0.3603 (4) | 0.35627 (14) | 0.0689 (10) | 0.853 (6) |
H3A | −0.0401 | 0.3560 | 0.3849 | 0.106 (10)* | 0.853 (6) |
H3B | 0.0581 | 0.4968 | 0.3485 | 0.080 (8)* | 0.853 (6) |
C3' | 0.0387 (13) | 0.158 (3) | 0.3562 (7) | 0.078 (7) | 0.147 (6) |
H3C | 0.0578 | 0.0174 | 0.3454 | 0.19 (13)* | 0.147 (6) |
H3D | −0.0447 | 0.1489 | 0.3837 | 0.18 (10)* | 0.147 (6) |
C4 | 0.1636 (2) | 0.2644 (3) | 0.39574 (11) | 0.0632 (6) | |
C41 | 0.1960 (4) | 0.3968 (8) | 0.46015 (19) | 0.1131 (17) | 0.853 (6) |
H41A | 0.2163 | 0.5238 | 0.4447 | 0.23 (4)* | 0.853 (6) |
H41B | 0.2713 | 0.3458 | 0.4889 | 0.20 (2)* | 0.853 (6) |
H41C | 0.1157 | 0.4023 | 0.4872 | 0.126 (11)* | 0.853 (6) |
C41' | 0.199 (2) | 0.113 (5) | 0.4626 (10) | 0.113 (10) | 0.147 (6) |
H41D | 0.1193 | 0.1182 | 0.4916 | 0.012 (19)* | 0.147 (6) |
H41E | 0.2778 | 0.1458 | 0.4875 | 0.12 (7)* | 0.147 (6) |
H41F | 0.2000 | −0.0168 | 0.4435 | 1.0 (11)* | 0.147 (6) |
C42 | 0.1273 (4) | 0.0584 (7) | 0.4159 (3) | 0.1091 (17) | 0.853 (6) |
H42A | 0.0573 | 0.0649 | 0.4491 | 0.143 (13)* | 0.853 (6) |
H42B | 0.2094 | 0.0021 | 0.4408 | 0.129 (18)* | 0.853 (6) |
H42C | 0.0996 | −0.0124 | 0.3768 | 0.18 (3)* | 0.853 (6) |
C42' | 0.1252 (17) | 0.471 (3) | 0.4094 (11) | 0.095 (8) | 0.147 (6) |
H42D | 0.0608 | 0.4451 | 0.4486 | 0.06 (4)* | 0.147 (6) |
H42E | 0.1057 | 0.5270 | 0.3775 | 2 (3)* | 0.147 (6) |
H42F | 0.2138 | 0.5056 | 0.4419 | 0.05 (6)* | 0.147 (6) |
C5 | 0.42048 (17) | 0.2570 (2) | 0.36645 (9) | 0.0431 (4) | |
C51 | 0.4814 (3) | 0.2428 (4) | 0.44148 (12) | 0.0711 (7) | |
H51A | 0.423 (6) | 0.177 (10) | 0.475 (3) | 0.074 (18)* | 0.50 |
H51B | 0.542 (5) | 0.378 (7) | 0.453 (2) | 0.066 (12)* | 0.50 |
H51C | 0.574 (4) | 0.133 (6) | 0.4421 (17) | 0.048 (10)* | 0.50 |
H51D | 0.577 (7) | 0.256 (9) | 0.445 (3) | 0.079 (16)* | 0.50 |
H51E | 0.433 (7) | 0.116 (10) | 0.460 (4) | 0.10 (3)* | 0.50 |
H51F | 0.451 (5) | 0.376 (7) | 0.467 (2) | 0.075 (12)* | 0.50 |
C6 | 0.51400 (16) | 0.2593 (2) | 0.31461 (10) | 0.0430 (4) | |
C7 | 0.47287 (16) | 0.26209 (19) | 0.24283 (9) | 0.0401 (4) | |
C71 | 0.5799 (2) | 0.2638 (3) | 0.19008 (12) | 0.0527 (5) | |
H71A | 0.666 (5) | 0.353 (6) | 0.211 (2) | 0.052 (12)* | 0.50 |
H71B | 0.539 (3) | 0.312 (5) | 0.1414 (18) | 0.035 (8)* | 0.50 |
H71C | 0.636 (3) | 0.146 (4) | 0.1935 (14) | 0.015 (6)* | 0.50 |
H71D | 0.556 (4) | 0.182 (7) | 0.152 (2) | 0.061 (12)* | 0.50 |
H71E | 0.694 (9) | 0.206 (11) | 0.209 (4) | 0.14 (3)* | 0.50 |
H71F | 0.626 (4) | 0.387 (6) | 0.185 (2) | 0.047 (11)* | 0.50 |
C8 | 0.33363 (17) | 0.2584 (2) | 0.22200 (9) | 0.0402 (4) | |
C81 | 0.2801 (2) | 0.2564 (3) | 0.14591 (10) | 0.0554 (5) | |
H81A | 0.394 (10) | 0.301 (12) | 0.115 (4) | 0.18 (3)* | 0.50 |
H81B | 0.198 (4) | 0.369 (6) | 0.137 (2) | 0.062 (11)* | 0.50 |
H81C | 0.211 (5) | 0.139 (7) | 0.135 (2) | 0.083 (15)* | 0.50 |
H81D | 0.183 (4) | 0.248 (6) | 0.142 (2) | 0.038 (10)* | 0.50 |
H81E | 0.310 (3) | 0.369 (4) | 0.1223 (15) | 0.025 (7)* | 0.50 |
H81F | 0.322 (3) | 0.142 (4) | 0.1225 (15) | 0.031 (7)* | 0.50 |
C9 | 0.24061 (15) | 0.2568 (2) | 0.27413 (9) | 0.0404 (4) | |
C10 | 0.27948 (17) | 0.2605 (2) | 0.34580 (9) | 0.0432 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0297 (7) | 0.0912 (11) | 0.0572 (8) | −0.0028 (5) | 0.0038 (6) | −0.0045 (6) |
O2 | 0.0324 (8) | 0.1445 (19) | 0.1126 (16) | −0.0033 (7) | 0.0080 (8) | −0.0141 (10) |
O6 | 0.0328 (7) | 0.0701 (9) | 0.0720 (9) | 0.0010 (5) | −0.0063 (6) | −0.0037 (6) |
C2 | 0.0309 (9) | 0.0837 (15) | 0.0806 (15) | 0.0025 (8) | 0.0117 (9) | 0.0036 (11) |
C3 | 0.0450 (12) | 0.093 (3) | 0.0706 (16) | 0.0158 (13) | 0.0189 (11) | 0.0000 (14) |
C3' | 0.044 (7) | 0.14 (2) | 0.051 (8) | −0.030 (9) | 0.013 (6) | 0.027 (10) |
C4 | 0.0504 (11) | 0.0904 (16) | 0.0512 (11) | 0.0091 (9) | 0.0184 (9) | 0.0034 (9) |
C41 | 0.084 (2) | 0.197 (5) | 0.0594 (18) | 0.051 (3) | 0.0124 (19) | −0.034 (3) |
C41' | 0.087 (14) | 0.21 (3) | 0.046 (9) | −0.046 (15) | 0.009 (10) | 0.052 (15) |
C42 | 0.081 (2) | 0.131 (3) | 0.121 (4) | 0.012 (2) | 0.047 (3) | 0.063 (3) |
C42' | 0.053 (9) | 0.144 (17) | 0.091 (14) | −0.012 (10) | 0.031 (10) | −0.051 (13) |
C5 | 0.0415 (9) | 0.0431 (9) | 0.0441 (9) | 0.0028 (6) | −0.0001 (7) | −0.0033 (6) |
C51 | 0.0623 (14) | 0.101 (2) | 0.0485 (12) | 0.0060 (13) | −0.0073 (10) | −0.0012 (12) |
C6 | 0.0303 (8) | 0.0404 (9) | 0.0578 (10) | 0.0020 (6) | 0.0006 (7) | 0.0002 (7) |
C7 | 0.0334 (8) | 0.0381 (8) | 0.0496 (9) | 0.0005 (5) | 0.0083 (6) | 0.0002 (6) |
C71 | 0.0419 (10) | 0.0527 (12) | 0.0657 (13) | 0.0001 (8) | 0.0187 (9) | 0.0003 (10) |
C8 | 0.0358 (8) | 0.0422 (9) | 0.0430 (9) | 0.0005 (6) | 0.0053 (6) | −0.0008 (6) |
C81 | 0.0495 (11) | 0.0737 (15) | 0.0428 (10) | −0.0023 (10) | 0.0022 (8) | 0.0003 (9) |
C9 | 0.0284 (7) | 0.0464 (9) | 0.0466 (9) | −0.0002 (6) | 0.0035 (6) | −0.0017 (7) |
C10 | 0.0399 (9) | 0.0466 (9) | 0.0440 (9) | 0.0003 (6) | 0.0085 (7) | −0.0005 (7) |
Geometric parameters (Å, º) top
O1—C2 | 1.331 (2) | C42—H41F | 0.999 (4) |
O1—C9 | 1.403 (2) | C42—H42A | 0.969 (3) |
O2—C2 | 1.197 (3) | C42—H42B | 0.982 (4) |
O6—C6 | 1.371 (2) | C42—H42C | 0.917 (7) |
O6—H6 | 0.96 (3) | C42'—H3B | 1.30 (2) |
C2—C3 | 1.496 (4) | C42'—H41A | 1.138 (19) |
C2—C3' | 1.538 (15) | C42'—H41C | 1.57 (2) |
C3—C3' | 1.40 (2) | C42'—H42D | 1.031 (16) |
C3—C42' | 1.487 (19) | C42'—H42E | 0.74 (3) |
C3—C4 | 1.542 (3) | C42'—H42F | 1.05 (2) |
C3—H3A | 0.972 (2) | C5—C6 | 1.399 (2) |
C3—H3B | 0.980 (3) | C5—C10 | 1.404 (2) |
C3—H42E | 1.377 (3) | C5—C51 | 1.514 (3) |
C3'—C42 | 1.543 (16) | C51—H51A | 0.99 (6) |
C3'—C4 | 1.568 (15) | C51—H51B | 1.12 (5) |
C3'—H3C | 1.02 (2) | C51—H51C | 1.18 (4) |
C3'—H3D | 1.005 (12) | C51—H51D | 0.94 (6) |
C3'—H42C | 1.37 (2) | C51—H51E | 1.08 (7) |
C4—C42' | 1.51 (2) | C51—H51F | 1.10 (5) |
C4—C42 | 1.528 (4) | C6—C7 | 1.401 (3) |
C4—C10 | 1.537 (2) | C7—C8 | 1.388 (2) |
C4—C41 | 1.549 (4) | C7—C71 | 1.508 (2) |
C4—C41' | 1.67 (2) | C71—H71A | 1.10 (4) |
C41—C42' | 1.26 (3) | C71—H71B | 1.04 (4) |
C41—C41' | 1.97 (4) | C71—H71C | 0.98 (3) |
C41—H41A | 0.954 (6) | C71—H71D | 0.94 (5) |
C41—H41B | 0.953 (4) | C71—H71E | 1.22 (9) |
C41—H41C | 0.972 (3) | C71—H71F | 0.98 (4) |
C41—H42D | 1.364 (4) | C8—C9 | 1.400 (2) |
C41—H42F | 0.855 (6) | C8—C81 | 1.509 (3) |
C41'—C42 | 1.15 (2) | C81—H81A | 1.34 (9) |
C41'—H41D | 0.987 (19) | C81—H81B | 1.12 (4) |
C41'—H41E | 0.91 (2) | C81—H81C | 1.07 (5) |
C41'—H41F | 0.97 (4) | C81—H81D | 0.95 (4) |
C41'—H42A | 1.42 (2) | C81—H81E | 0.96 (3) |
C41'—H42B | 0.89 (4) | C81—H81F | 1.01 (3) |
C42—H3C | 1.490 (7) | C9—C10 | 1.395 (2) |
C42—H41D | 1.515 (6) | | |
| | | |
C2—O1—C9 | 122.16 (16) | H3C—C42—H41F | 129.4 (5) |
C6—O6—H6 | 116 (2) | H41D—C42—H41F | 74.0 (4) |
O2—C2—O1 | 118.3 (2) | C41'—C42—H42A | 83.7 (11) |
O2—C2—C3 | 126.5 (2) | C4—C42—H42A | 108.1 (4) |
O1—C2—C3 | 114.44 (17) | C3'—C42—H42A | 94.6 (6) |
O2—C2—C3' | 115.7 (5) | H3C—C42—H42A | 107.9 (4) |
O1—C2—C3' | 105.3 (6) | H41D—C42—H42A | 43.1 (3) |
C3—C2—C3' | 54.9 (8) | H41F—C42—H42A | 100.8 (4) |
C3'—C3—C42' | 120.8 (12) | C41'—C42—H42B | 48.2 (17) |
C3'—C3—C2 | 64.1 (6) | C4—C42—H42B | 107.3 (4) |
C42'—C3—C2 | 157.1 (6) | C3'—C42—H42B | 158.2 (5) |
C3'—C3—C4 | 64.2 (6) | H3C—C42—H42B | 131.5 (5) |
C42'—C3—C4 | 59.6 (9) | H41D—C42—H42B | 75.2 (4) |
C2—C3—C4 | 112.49 (19) | H41F—C42—H42B | 9.78 (4) |
C3'—C3—H3A | 88.5 (5) | H42A—C42—H42B | 106.9 (5) |
C42'—C3—H3A | 93.7 (5) | C41'—C42—H42C | 158.3 (16) |
C2—C3—H3A | 109.0 (2) | C4—C42—H42C | 110.8 (3) |
C4—C3—H3A | 109.9 (2) | C3'—C42—H42C | 61.6 (9) |
C3'—C3—H3B | 164.6 (5) | H3C—C42—H42C | 22.39 (15) |
C42'—C3—H3B | 59.7 (10) | H41D—C42—H42C | 153.1 (3) |
C2—C3—H3B | 109.3 (2) | H41F—C42—H42C | 107.7 (4) |
C4—C3—H3B | 109.1 (2) | H42A—C42—H42C | 112.4 (5) |
H3A—C3—H3B | 106.9 (2) | H42B—C42—H42C | 111.2 (4) |
C3'—C3—H42E | 146.8 (6) | C41—C42'—C3 | 124.9 (18) |
C42'—C3—H42E | 29.5 (10) | C41—C42'—C4 | 67.6 (12) |
C2—C3—H42E | 135.3 (2) | C3—C42'—C4 | 62.0 (7) |
C4—C3—H42E | 82.56 (16) | C41—C42'—H3B | 162.9 (17) |
H3A—C3—H42E | 103.9 (2) | C3—C42'—H3B | 40.5 (6) |
H3B—C3—H42E | 30.30 (9) | C4—C42'—H3B | 95.3 (11) |
C3—C3'—C2 | 61.0 (7) | C41—C42'—H41A | 46.6 (9) |
C3—C3'—C42 | 116.8 (12) | C3—C42'—H41A | 162.7 (15) |
C2—C3'—C42 | 160.4 (9) | C4—C42'—H41A | 102.6 (16) |
C3—C3'—C4 | 62.3 (8) | H3B—C42'—H41A | 143.4 (19) |
C2—C3'—C4 | 108.8 (10) | C41—C42'—H41C | 38.2 (7) |
C42—C3'—C4 | 58.8 (6) | C3—C42'—H41C | 114.8 (12) |
C3—C3'—H3C | 163.8 (11) | C4—C42'—H41C | 84.9 (13) |
C2—C3'—H3C | 109.2 (12) | H3B—C42'—H41C | 145.6 (11) |
C42—C3'—H3C | 67.6 (10) | H41A—C42'—H41C | 68.6 (12) |
C4—C3'—H3C | 113.5 (12) | C41—C42'—H42D | 72.4 (15) |
C3—C3'—H3D | 93.5 (16) | C3—C42'—H42D | 93.4 (11) |
C2—C3'—H3D | 108.6 (13) | C4—C42'—H42D | 97.9 (17) |
C42—C3'—H3D | 90.8 (9) | H3B—C42'—H42D | 112.3 (15) |
C4—C3'—H3D | 114.2 (14) | H41A—C42'—H42D | 96.7 (17) |
H3C—C3'—H3D | 102.2 (14) | H41C—C42'—H42D | 34.5 (8) |
C3—C3'—H42C | 150.1 (11) | C41—C42'—H42E | 161.3 (18) |
C2—C3'—H42C | 137.8 (14) | C3—C42'—H42E | 67.0 (14) |
C42—C3'—H42C | 36.1 (5) | C4—C42'—H42E | 114.3 (17) |
C4—C3'—H42C | 87.8 (8) | H3B—C42'—H42E | 26.7 (8) |
H3C—C3'—H42C | 31.5 (6) | H41A—C42'—H42E | 117 (2) |
H3D—C3'—H42C | 98.3 (12) | H41C—C42'—H42E | 156.0 (17) |
C42'—C4—C42 | 141.1 (7) | H42D—C42'—H42E | 124 (2) |
C42'—C4—C10 | 109.3 (6) | C41—C42'—H42F | 42.3 (9) |
C42—C4—C10 | 109.64 (19) | C3—C42'—H42F | 157.4 (16) |
C42'—C4—C3 | 58.4 (8) | C4—C42'—H42F | 96.7 (16) |
C42—C4—C3 | 109.6 (3) | H3B—C42'—H42F | 145.9 (19) |
C10—C4—C3 | 107.47 (16) | H41A—C42'—H42F | 5.85 (12) |
C42'—C4—C41 | 48.6 (9) | H41C—C42'—H42F | 67.4 (13) |
C42—C4—C41 | 113.0 (3) | H42D—C42'—H42F | 97.5 (18) |
C10—C4—C41 | 112.9 (2) | H42E—C42'—H42F | 121 (2) |
C3—C4—C41 | 103.9 (2) | C6—C5—C10 | 118.70 (16) |
C42'—C4—C3' | 109.5 (11) | C6—C5—C51 | 116.26 (17) |
C42—C4—C3' | 59.8 (7) | C10—C5—C51 | 125.00 (17) |
C10—C4—C3' | 105.9 (5) | C5—C51—H51A | 116 (3) |
C3—C4—C3' | 53.5 (8) | C5—C51—H51B | 107 (2) |
C41—C4—C3' | 139.9 (6) | H51A—C51—H51B | 125 (4) |
C42'—C4—C41' | 120.2 (14) | C5—C51—H51C | 107.2 (16) |
C42—C4—C41' | 42.1 (10) | H51A—C51—H51C | 100 (4) |
C10—C4—C41' | 110.4 (8) | H51B—C51—H51C | 98 (3) |
C3—C4—C41' | 139.0 (7) | C5—C51—H51D | 112 (3) |
C41—C4—C41' | 75.2 (12) | H51A—C51—H51D | 128 (5) |
C3'—C4—C41' | 100.5 (11) | H51B—C51—H51D | 53 (3) |
C42'—C41—C4 | 63.9 (8) | H51C—C51—H51D | 46 (3) |
C42'—C41—C41' | 115.5 (12) | C5—C51—H51E | 103 (4) |
C4—C41—C41' | 55.1 (6) | H51A—C51—H51E | 29 (5) |
C42'—C41—H41A | 60.1 (9) | H51B—C51—H51E | 149 (4) |
C4—C41—H41A | 109.6 (3) | H51C—C51—H51E | 80 (4) |
C41'—C41—H41A | 158.0 (5) | H51D—C51—H51E | 121 (5) |
C42'—C41—H41B | 162.2 (7) | C5—C51—H51F | 106 (2) |
C4—C41—H41B | 110.0 (4) | H51A—C51—H51F | 85 (4) |
C41'—C41—H41B | 66.9 (8) | H51B—C51—H51F | 51 (2) |
H41A—C41—H41B | 110.5 (5) | H51C—C51—H51F | 140 (3) |
C42'—C41—H41C | 88.7 (7) | H51D—C51—H51F | 101 (4) |
C4—C41—H41C | 108.8 (4) | H51E—C51—H51F | 113 (5) |
C41'—C41—H41C | 92.1 (7) | O6—C6—C5 | 115.66 (17) |
H41A—C41—H41C | 108.9 (4) | O6—C6—C7 | 121.57 (16) |
H41B—C41—H41C | 109.0 (4) | C5—C6—C7 | 122.76 (15) |
C42'—C41—H42D | 46.1 (6) | C8—C7—C6 | 118.84 (15) |
C4—C41—H42D | 83.1 (2) | C8—C7—C71 | 121.51 (17) |
C41'—C41—H42D | 105.0 (7) | C6—C7—C71 | 119.64 (15) |
H41A—C41—H42D | 86.9 (3) | C7—C71—H71A | 108 (2) |
H41B—C41—H42D | 151.7 (4) | C7—C71—H71B | 111.3 (17) |
H41C—C41—H42D | 42.84 (14) | H71A—C71—H71B | 112 (3) |
C42'—C41—H42F | 56.1 (9) | C7—C71—H71C | 111.2 (15) |
C4—C41—H42F | 103.5 (3) | H71A—C71—H71C | 92 (3) |
C41'—C41—H42F | 152.8 (6) | H71B—C71—H71C | 120 (2) |
H41A—C41—H42F | 6.15 (5) | C7—C71—H71D | 112 (2) |
H41B—C41—H42F | 113.0 (5) | H71A—C71—H71D | 140 (3) |
H41C—C41—H42F | 112.4 (4) | H71B—C71—H71D | 56 (3) |
H42D—C41—H42F | 86.7 (3) | H71C—C71—H71D | 70 (3) |
C42—C41'—C4 | 62.5 (9) | C7—C71—H71E | 118 (4) |
C42—C41'—C41 | 107.8 (17) | H71A—C71—H71E | 54 (4) |
C4—C41'—C41 | 49.6 (8) | H71B—C71—H71E | 131 (4) |
C42—C41'—H41D | 89.7 (17) | H71C—C71—H71E | 38 (4) |
C4—C41'—H41D | 107 (2) | H71D—C71—H71E | 102 (5) |
C41—C41'—H41D | 88 (2) | C7—C71—H71F | 115 (2) |
C42—C41'—H41E | 158 (3) | H71A—C71—H71F | 36 (3) |
C4—C41'—H41E | 111.3 (19) | H71B—C71—H71F | 78 (3) |
C41—C41'—H41E | 77 (2) | H71C—C71—H71F | 118 (3) |
H41D—C41'—H41E | 112 (2) | H71D—C71—H71F | 123 (3) |
C42—C41'—H41F | 55.2 (15) | H71E—C71—H71F | 84 (4) |
C4—C41'—H41F | 107.6 (16) | C7—C8—C9 | 118.10 (15) |
C41—C41'—H41F | 156.6 (14) | C7—C8—C81 | 122.49 (16) |
H41D—C41'—H41F | 106 (2) | C9—C8—C81 | 119.41 (16) |
H41E—C41'—H41F | 113 (3) | C8—C81—H81A | 101 (4) |
C42—C41'—H42A | 42.6 (8) | C8—C81—H81B | 109.2 (19) |
C4—C41'—H42A | 82.5 (11) | H81A—C81—H81B | 112 (4) |
C41—C41'—H42A | 102.8 (17) | C8—C81—H81C | 111 (2) |
H41D—C41'—H42A | 47.2 (9) | H81A—C81—H81C | 129 (4) |
H41E—C41'—H42A | 158.6 (19) | H81B—C81—H81C | 94 (4) |
H41F—C41'—H42A | 75.9 (16) | C8—C81—H81D | 111 (2) |
C42—C41'—H42B | 55.7 (16) | H81A—C81—H81D | 147 (5) |
C4—C41'—H42B | 102.2 (15) | H81B—C81—H81D | 48 (2) |
C41—C41'—H42B | 149.3 (13) | H81C—C81—H81D | 48 (3) |
H41D—C41'—H42B | 115 (3) | C8—C81—H81E | 110.4 (17) |
H41E—C41'—H42B | 110 (3) | H81A—C81—H81E | 46 (4) |
H41F—C41'—H42B | 9.0 (4) | H81B—C81—H81E | 67 (2) |
H42A—C41'—H42B | 81.9 (19) | H81C—C81—H81E | 138 (3) |
C41'—C42—C4 | 75.5 (14) | H81D—C81—H81E | 111 (3) |
C41'—C42—C3' | 134.1 (18) | C8—C81—H81F | 108.1 (16) |
C4—C42—C3' | 61.4 (7) | H81A—C81—H81F | 67 (4) |
C41'—C42—H3C | 165.8 (8) | H81B—C81—H81F | 142 (3) |
C4—C42—H3C | 92.8 (2) | H81C—C81—H81F | 66 (3) |
C3'—C42—H3C | 39.2 (8) | H81D—C81—H81F | 111 (3) |
C41'—C42—H41D | 40.7 (10) | H81E—C81—H81F | 106 (3) |
C4—C42—H41D | 90.9 (3) | C10—C9—C8 | 123.89 (15) |
C3'—C42—H41D | 121.2 (8) | C10—C9—O1 | 122.53 (15) |
H3C—C42—H41D | 149.9 (2) | C8—C9—O1 | 113.45 (15) |
C41'—C42—H41F | 53.1 (17) | C9—C10—C5 | 117.63 (16) |
C4—C42—H41F | 116.8 (4) | C9—C10—C4 | 116.96 (16) |
C3'—C42—H41F | 164.0 (8) | C5—C10—C4 | 125.40 (17) |
| | | |
C9—O1—C2—O2 | −176.27 (16) | C42'—C41—C41'—C42 | −2.5 (16) |
C9—O1—C2—C3 | 12.8 (3) | C4—C41—C41'—C42 | −24.5 (8) |
C9—O1—C2—C3' | −45.2 (8) | C42'—C41—C41'—C4 | 22.1 (9) |
O2—C2—C3—C3' | 98.0 (6) | C41—C41'—C42—C4 | 20.9 (6) |
O1—C2—C3—C3' | −92.0 (6) | C4—C41'—C42—C3' | −20.2 (14) |
O2—C2—C3—C42' | −154 (3) | C41—C41'—C42—C3' | 1 (2) |
O1—C2—C3—C42' | 16 (3) | C42'—C4—C42—C41' | −79.7 (19) |
C3'—C2—C3—C42' | 108 (3) | C10—C4—C42—C41' | 99.0 (14) |
O2—C2—C3—C4 | 141.5 (2) | C3—C4—C42—C41' | −143.3 (13) |
O1—C2—C3—C4 | −48.4 (3) | C41—C4—C42—C41' | −28.0 (14) |
C3'—C2—C3—C4 | 43.6 (6) | C3'—C4—C42—C41' | −163.6 (15) |
C42'—C3—C3'—C2 | −154.5 (7) | C42'—C4—C42—C3' | 83.9 (16) |
C4—C3—C3'—C2 | −135.0 (5) | C10—C4—C42—C3' | −97.4 (7) |
C42'—C3—C3'—C42 | 3.4 (12) | C3—C4—C42—C3' | 20.3 (7) |
C2—C3—C3'—C42 | 157.9 (10) | C41—C4—C42—C3' | 135.6 (7) |
C4—C3—C3'—C42 | 22.9 (6) | C41'—C4—C42—C3' | 163.6 (15) |
C42'—C3—C3'—C4 | −19.5 (8) | C3—C3'—C42—C41' | −1.4 (19) |
C2—C3—C3'—C4 | 135.0 (5) | C2—C3'—C42—C41' | 77 (5) |
O2—C2—C3'—C3 | −118.0 (4) | C4—C3'—C42—C41' | 22.4 (16) |
O1—C2—C3'—C3 | 109.4 (4) | C3—C3'—C42—C4 | −23.8 (6) |
O2—C2—C3'—C42 | 153 (4) | C2—C3'—C42—C4 | 55 (5) |
O1—C2—C3'—C42 | 20 (5) | C4—C41—C42'—C3 | 25.0 (8) |
C3—C2—C3'—C42 | −89 (5) | C41'—C41—C42'—C3 | 4.9 (14) |
O2—C2—C3'—C4 | −159.4 (6) | C41'—C41—C42'—C4 | −20.1 (8) |
O1—C2—C3'—C4 | 68.0 (12) | C3'—C3—C42'—C41 | −5.8 (15) |
C3—C2—C3'—C4 | −41.4 (8) | C2—C3—C42'—C41 | −102 (3) |
C3'—C3—C4—C42' | −160.6 (10) | C4—C3—C42'—C41 | −26.3 (8) |
C2—C3—C4—C42' | 156.0 (8) | C3'—C3—C42'—C4 | 20.4 (9) |
C3'—C3—C4—C42 | −21.9 (6) | C2—C3—C42'—C4 | −75 (3) |
C42'—C3—C4—C42 | 138.7 (8) | C42—C4—C42'—C41 | 74.7 (12) |
C2—C3—C4—C42 | −65.4 (3) | C10—C4—C42'—C41 | −104.0 (7) |
C3'—C3—C4—C10 | 97.2 (6) | C3—C4—C42'—C41 | 156.9 (9) |
C42'—C3—C4—C10 | −102.3 (8) | C3'—C4—C42'—C41 | 140.4 (6) |
C2—C3—C4—C10 | 53.7 (2) | C41'—C4—C42'—C41 | 25.0 (11) |
C3'—C3—C4—C41 | −142.9 (6) | C42—C4—C42'—C3 | −82.2 (14) |
C42'—C3—C4—C41 | 17.7 (8) | C10—C4—C42'—C3 | 99.1 (4) |
C2—C3—C4—C41 | 173.6 (3) | C41—C4—C42'—C3 | −156.9 (9) |
C42'—C3—C4—C3' | 160.6 (10) | C3'—C4—C42'—C3 | −16.5 (8) |
C2—C3—C4—C3' | −43.5 (6) | C41'—C4—C42'—C3 | −131.9 (9) |
C3'—C3—C4—C41' | −59.5 (19) | C10—C5—C6—O6 | 178.96 (12) |
C42'—C3—C4—C41' | 101.1 (19) | C51—C5—C6—O6 | −3.4 (2) |
C2—C3—C4—C41' | −103.0 (18) | C10—C5—C6—C7 | −1.0 (2) |
C3—C3'—C4—C42' | 17.5 (10) | C51—C5—C6—C7 | 176.68 (16) |
C2—C3'—C4—C42' | 58.3 (13) | O6—C6—C7—C8 | 178.70 (13) |
C42—C3'—C4—C42' | −138.5 (9) | C5—C6—C7—C8 | −1.3 (2) |
C3—C3'—C4—C42 | 156.0 (7) | O6—C6—C7—C71 | 0.3 (2) |
C2—C3'—C4—C42 | −163.2 (14) | C5—C6—C7—C71 | −179.77 (15) |
C3—C3'—C4—C10 | −100.2 (5) | C6—C7—C8—C9 | 1.51 (19) |
C2—C3'—C4—C10 | −59.4 (12) | C71—C7—C8—C9 | 179.92 (14) |
C42—C3'—C4—C10 | 103.8 (4) | C6—C7—C8—C81 | −178.56 (15) |
C2—C3'—C4—C3 | 40.8 (8) | C71—C7—C8—C81 | −0.2 (2) |
C42—C3'—C4—C3 | −156.0 (7) | C7—C8—C9—C10 | 0.6 (2) |
C3—C3'—C4—C41 | 65.5 (9) | C81—C8—C9—C10 | −179.30 (15) |
C2—C3'—C4—C41 | 106.3 (8) | C7—C8—C9—O1 | −175.26 (12) |
C42—C3'—C4—C41 | −90.6 (11) | C81—C8—C9—O1 | 4.8 (2) |
C3—C3'—C4—C41' | 144.9 (11) | C2—O1—C9—C10 | 15.8 (2) |
C2—C3'—C4—C41' | −174.3 (14) | C2—O1—C9—C8 | −168.30 (15) |
C42—C3'—C4—C41' | −11.1 (12) | C8—C9—C10—C5 | −2.9 (2) |
C42—C4—C41—C42' | −138.9 (8) | O1—C9—C10—C5 | 172.59 (13) |
C10—C4—C41—C42' | 96.0 (8) | C8—C9—C10—C4 | 178.12 (14) |
C3—C4—C41—C42' | −20.2 (8) | O1—C9—C10—C4 | −6.4 (2) |
C3'—C4—C41—C42' | −69.0 (13) | C6—C5—C10—C9 | 3.01 (19) |
C41'—C4—C41—C42' | −157.8 (11) | C51—C5—C10—C9 | −174.45 (17) |
C42'—C4—C41—C41' | 157.8 (11) | C6—C5—C10—C4 | −178.13 (14) |
C42—C4—C41—C41' | 18.9 (7) | C51—C5—C10—C4 | 4.4 (3) |
C10—C4—C41—C41' | −106.2 (7) | C42'—C4—C10—C9 | −89.0 (9) |
C3—C4—C41—C41' | 137.6 (7) | C42—C4—C10—C9 | 91.9 (3) |
C3'—C4—C41—C41' | 88.8 (13) | C3—C4—C10—C9 | −27.2 (2) |
C42'—C4—C41'—C42 | 134.4 (12) | C41—C4—C10—C9 | −141.2 (3) |
C10—C4—C41'—C42 | −97.1 (9) | C3'—C4—C10—C9 | 28.8 (8) |
C3—C4—C41'—C42 | 59 (2) | C41'—C4—C10—C9 | 136.7 (12) |
C41—C4—C41'—C42 | 153.5 (12) | C42'—C4—C10—C5 | 92.1 (9) |
C3'—C4—C41'—C42 | 14.4 (14) | C42—C4—C10—C5 | −87.0 (3) |
C42'—C4—C41'—C41 | −19.1 (9) | C3—C4—C10—C5 | 153.96 (18) |
C42—C4—C41'—C41 | −153.5 (12) | C41—C4—C10—C5 | 39.9 (3) |
C10—C4—C41'—C41 | 109.4 (5) | C3'—C4—C10—C5 | −150.0 (8) |
C3—C4—C41'—C41 | −94.4 (13) | C41'—C4—C10—C5 | −42.1 (12) |
C3'—C4—C41'—C41 | −139.1 (7) | | |
(cum293) 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin
top
Crystal data top
C14H18O3 | V = 1285.0 (4) Å3 |
Mr = 234.28 | Z = 4 |
P21/c, monoclinic | F(000) = 504 |
a = 9.744 (2) Å | Dx = 1.211 Mg m−3 |
b = 6.922 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 19.109 (4) Å | µ = 0.08 mm−1 |
α = 90° | T = 293 K |
β = 94.44 (3)° | , colourlees |
γ = 90° | 0.35 × 0.25 × 0.12 mm |
Data collection top
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 25.1°, θmin = 2.1° |
10609 measured reflections | h = −11→11 |
2273 independent reflections | k = −8→6 |
2059 reflections with I > 2σ(I) | l = −22→22 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.120 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.327 | w = 1/[σ2(Fo2) + (0.1331P)2 + 0.7198P] where P = (Fo2 + 2Fc2)/3 |
S = 1.36 | (Δ/σ)max = 0.202 |
2273 reflections | Δρmax = 0.41 e Å−3 |
254 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.030 (8) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.1032 (3) | 0.2393 (4) | 0.24762 (15) | 0.0613 (9) | |
O2 | −0.1144 (3) | 0.2401 (5) | 0.2618 (2) | 0.0976 (15) | |
O6 | 0.6496 (3) | 0.2573 (4) | 0.3385 (2) | 0.0609 (9) | |
H6 | 0.700 (6) | 0.250 (6) | 0.311 (3) | 0.078 (19)* | |
C2 | −0.0008 (4) | 0.2641 (6) | 0.2870 (3) | 0.0647 (13) | |
C3 | 0.0389 (5) | 0.3558 (10) | 0.3563 (3) | 0.0734 (19) | 0.80 |
H3A | −0.0390 | 0.3495 | 0.3850 | 0.058 (14)* | 0.80 |
H3B | 0.0581 | 0.4937 | 0.3493 | 0.074 (18)* | 0.80 |
C3' | 0.041 (3) | 0.139 (3) | 0.3580 (13) | 0.082 (8) | 0.20 |
H31A | 0.03 (3) | 0.08 (4) | 0.315 (16) | 0.122* | 0.20 |
H31B | −0.05 (3) | 0.21 (4) | 0.400 (17) | 0.122* | 0.20 |
C4 | 0.1634 (5) | 0.2618 (6) | 0.3955 (2) | 0.0642 (13) | |
C41 | 0.1986 (18) | 0.394 (3) | 0.4597 (9) | 0.161 (9) | 0.80 |
H41A | 0.102 (9) | 0.385 (14) | 0.485 (4) | 0.17 (3)* | |
H41B | 0.181 (5) | 0.434 (6) | 0.456 (3) | 0.013 (10)* | |
H41C | 0.224 (10) | 0.263 (11) | 0.491 (5) | 0.15 (3)* | |
C41' | 0.181 (3) | 0.116 (5) | 0.4599 (17) | 0.080 (7)* | 0.20 |
C42 | 0.1276 (8) | 0.0539 (14) | 0.4162 (5) | 0.100 (3) | 0.80 |
H42A | 0.057 (11) | 0.076 (15) | 0.459 (6) | 0.18 (4)* | 0.80 |
H42B | 0.219 (4) | 0.023 (6) | 0.4525 (19) | 0.020 (9)* | 0.80 |
H42C | 0.091 (6) | −0.029 (8) | 0.370 (3) | 0.072 (18)* | 0.80 |
C42' | 0.118 (3) | 0.468 (5) | 0.4062 (17) | 0.093 (8)* | 0.20 |
H42D | 0.11 (3) | 0.59 (5) | 0.479 (16) | 0.139* | 0.20 |
H42E | 0.10 (3) | 0.62 (5) | 0.378 (17) | 0.139* | 0.20 |
H42F | 0.22 (4) | 0.55 (5) | 0.425 (19) | 0.139* | 0.20 |
C5 | 0.4201 (4) | 0.2560 (4) | 0.36604 (19) | 0.0432 (9) | |
C51 | 0.4805 (5) | 0.2450 (7) | 0.4413 (2) | 0.0737 (15) | |
H51A | 0.4075 | 0.2450 | 0.4723 | 0.111* | |
H51B | 0.5391 | 0.3546 | 0.4514 | 0.111* | |
H51C | 0.5333 | 0.1284 | 0.4480 | 0.111* | |
C6 | 0.5137 (3) | 0.2573 (4) | 0.3144 (2) | 0.0418 (9) | |
C7 | 0.4727 (3) | 0.2604 (4) | 0.24260 (19) | 0.0390 (9) | |
C71 | 0.5803 (4) | 0.2606 (6) | 0.1905 (3) | 0.0517 (11) | |
H71A | 0.536 (7) | 0.269 (7) | 0.145 (4) | 0.11 (2)* | |
H71B | 0.641 (4) | 0.146 (6) | 0.195 (2) | 0.067 (12)* | |
H71C | 0.640 (5) | 0.374 (8) | 0.192 (3) | 0.098 (16)* | |
C8 | 0.3332 (4) | 0.2568 (4) | 0.22213 (19) | 0.0399 (9) | |
C81 | 0.2804 (5) | 0.2560 (7) | 0.1466 (2) | 0.0551 (11) | |
H81A | 0.337 (7) | 0.307 (10) | 0.111 (4) | 0.028 (16)* | 0.50 |
H81B | 0.192 (7) | 0.303 (9) | 0.135 (3) | 0.010 (13)* | 0.50 |
H81C | 0.255 (8) | 0.126 (9) | 0.130 (3) | 0.017 (14)* | 0.50 |
H81D | 0.180 (11) | 0.198 (16) | 0.140 (5) | 0.08 (3)* | 0.50 |
H81E | 0.325 (6) | 0.154 (9) | 0.121 (3) | 0.016 (14)* | 0.50 |
H81F | 0.270 (12) | 0.382 (15) | 0.126 (5) | 0.08 (3)* | 0.50 |
C9 | 0.2413 (3) | 0.2543 (4) | 0.27436 (19) | 0.0406 (9) | |
C10 | 0.2794 (4) | 0.2597 (4) | 0.34560 (19) | 0.0425 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0307 (15) | 0.094 (2) | 0.0591 (18) | −0.0043 (11) | 0.0018 (12) | −0.0051 (14) |
O2 | 0.0316 (17) | 0.148 (4) | 0.113 (3) | −0.0074 (16) | 0.0077 (17) | −0.020 (2) |
O6 | 0.0321 (15) | 0.072 (2) | 0.078 (2) | −0.0005 (11) | −0.0045 (14) | −0.0065 (14) |
C2 | 0.033 (2) | 0.079 (3) | 0.083 (3) | 0.0036 (17) | 0.015 (2) | 0.005 (2) |
C3 | 0.036 (3) | 0.121 (6) | 0.067 (4) | 0.010 (3) | 0.022 (2) | −0.014 (4) |
C3' | 0.110 (18) | 0.059 (13) | 0.081 (16) | −0.066 (13) | 0.040 (14) | −0.043 (12) |
C4 | 0.052 (2) | 0.090 (3) | 0.052 (2) | 0.008 (2) | 0.0169 (19) | 0.004 (2) |
C41 | 0.143 (11) | 0.25 (2) | 0.091 (8) | 0.101 (12) | 0.043 (7) | −0.031 (9) |
C42 | 0.074 (5) | 0.141 (7) | 0.088 (6) | −0.002 (5) | 0.023 (5) | 0.049 (6) |
C5 | 0.044 (2) | 0.0422 (19) | 0.043 (2) | 0.0014 (14) | 0.0005 (15) | −0.0018 (14) |
C51 | 0.065 (3) | 0.107 (4) | 0.047 (3) | 0.007 (2) | −0.010 (2) | −0.001 (2) |
C6 | 0.0288 (17) | 0.0368 (17) | 0.059 (2) | −0.0004 (12) | −0.0003 (15) | −0.0049 (14) |
C7 | 0.0364 (18) | 0.0297 (16) | 0.052 (2) | −0.0004 (12) | 0.0083 (15) | −0.0029 (13) |
C71 | 0.042 (2) | 0.048 (2) | 0.067 (3) | 0.0064 (16) | 0.0184 (19) | 0.0049 (19) |
C8 | 0.0384 (19) | 0.0377 (17) | 0.044 (2) | −0.0018 (13) | 0.0053 (15) | −0.0023 (14) |
C81 | 0.053 (3) | 0.068 (3) | 0.044 (2) | 0.001 (2) | 0.0033 (19) | −0.003 (2) |
C9 | 0.0297 (17) | 0.0473 (19) | 0.045 (2) | 0.0018 (13) | 0.0018 (14) | 0.0051 (14) |
C10 | 0.0390 (19) | 0.0443 (19) | 0.045 (2) | 0.0003 (13) | 0.0075 (15) | 0.0010 (14) |
Geometric parameters (Å, º) top
O1—C2 | 1.320 (5) | C4—C42 | 1.540 (9) |
O1—C9 | 1.405 (4) | C4—C41' | 1.59 (3) |
O2—C2 | 1.185 (6) | C41—C42' | 1.34 (4) |
O6—C6 | 1.368 (4) | C41—C41' | 1.93 (4) |
C2—C3 | 1.492 (8) | C41'—C42 | 1.04 (3) |
C2—C3' | 1.63 (3) | C5—C6 | 1.394 (5) |
C3—C42' | 1.41 (3) | C5—C10 | 1.396 (5) |
C3—C3' | 1.50 (2) | C5—C51 | 1.513 (5) |
C3—C4 | 1.522 (7) | C6—C7 | 1.400 (5) |
C3'—C42 | 1.47 (3) | C7—C8 | 1.385 (5) |
C3'—C4 | 1.59 (2) | C7—C71 | 1.501 (5) |
C4—C42' | 1.51 (3) | C8—C9 | 1.392 (5) |
C4—C10 | 1.534 (5) | C8—C81 | 1.495 (5) |
C4—C41 | 1.546 (18) | C9—C10 | 1.384 (5) |
| | | |
C2—O1—C9 | 122.6 (3) | C3—C4—C3' | 57.5 (12) |
O2—C2—O1 | 119.0 (5) | C10—C4—C3' | 106.2 (9) |
O2—C2—C3 | 126.2 (4) | C41—C4—C3' | 141.7 (11) |
O1—C2—C3 | 113.8 (4) | C42—C4—C3' | 56.0 (11) |
O2—C2—C3' | 115.3 (8) | C41'—C4—C3' | 92.6 (16) |
O1—C2—C3' | 104.7 (9) | C42'—C41—C4 | 62.8 (16) |
C3—C2—C3' | 57.1 (7) | C42'—C41—C41' | 110 (2) |
C42'—C3—C2 | 157.6 (13) | C4—C41—C41' | 53.1 (12) |
C42'—C3—C3' | 122.1 (18) | C42—C41'—C4 | 68.0 (19) |
C2—C3—C3' | 66.1 (11) | C42—C41'—C41 | 117 (3) |
C42'—C3—C4 | 62.0 (13) | C4—C41'—C41 | 51.1 (10) |
C2—C3—C4 | 113.4 (4) | C41'—C42—C3' | 131 (2) |
C3'—C3—C4 | 63.5 (11) | C41'—C42—C4 | 73.1 (18) |
C42—C3'—C3 | 115.1 (14) | C3'—C42—C4 | 63.7 (7) |
C42—C3'—C4 | 60.3 (11) | C41—C42'—C3 | 124 (3) |
C3—C3'—C4 | 59.0 (6) | C41—C42'—C4 | 65.2 (16) |
C42—C3'—C2 | 159.0 (15) | C3—C42'—C4 | 62.6 (13) |
C3—C3'—C2 | 56.7 (10) | C6—C5—C10 | 118.9 (3) |
C4—C3'—C2 | 102.8 (11) | C6—C5—C51 | 116.4 (4) |
C42'—C4—C3 | 55.4 (13) | C10—C5—C51 | 124.6 (4) |
C42'—C4—C10 | 109.3 (12) | O6—C6—C5 | 115.5 (4) |
C3—C4—C10 | 107.2 (3) | O6—C6—C7 | 121.7 (3) |
C42'—C4—C41 | 52.0 (14) | C5—C6—C7 | 122.8 (3) |
C3—C4—C41 | 104.9 (7) | C8—C7—C6 | 118.4 (3) |
C10—C4—C41 | 111.7 (8) | C8—C7—C71 | 122.2 (3) |
C42'—C4—C42 | 140.5 (12) | C6—C7—C71 | 119.3 (3) |
C3—C4—C42 | 109.8 (5) | C9—C8—C7 | 118.0 (3) |
C10—C4—C42 | 110.1 (4) | C9—C8—C81 | 120.0 (3) |
C41—C4—C42 | 112.8 (10) | C7—C8—C81 | 122.0 (3) |
C42'—C4—C41' | 120.5 (17) | C8—C9—C10 | 124.5 (3) |
C3—C4—C41' | 133.5 (12) | C8—C9—O1 | 113.0 (3) |
C10—C4—C41' | 115.7 (12) | C10—C9—O1 | 122.4 (3) |
C41—C4—C41' | 75.8 (15) | C9—C10—C5 | 117.2 (3) |
C42—C4—C41' | 38.9 (12) | C9—C10—C4 | 117.2 (3) |
C42'—C4—C3' | 110.2 (16) | C5—C10—C4 | 125.5 (4) |
| | | |
C9—O1—C2—O2 | −176.3 (4) | C42'—C41—C41'—C42 | 10 (3) |
C9—O1—C2—C3 | 14.4 (6) | C4—C41—C41'—C42 | −19.0 (18) |
C9—O1—C2—C3' | −45.8 (7) | C42'—C41—C41'—C4 | 28.6 (18) |
O2—C2—C3—C42' | −144 (4) | C4—C41'—C42—C3' | −28 (2) |
O1—C2—C3—C42' | 24 (4) | C41—C41'—C42—C3' | −12 (4) |
C3'—C2—C3—C42' | 117 (4) | C41—C41'—C42—C4 | 15.8 (15) |
O2—C2—C3—C3' | 99.1 (11) | C3—C3'—C42—C41' | 7 (3) |
O1—C2—C3—C3' | −92.6 (11) | C4—C3'—C42—C41' | 30 (3) |
O2—C2—C3—C4 | 142.8 (5) | C2—C3'—C42—C41' | 69 (5) |
O1—C2—C3—C4 | −48.8 (6) | C3—C3'—C42—C4 | −22.7 (10) |
C3'—C2—C3—C4 | 43.8 (11) | C2—C3'—C42—C4 | 39 (4) |
C42'—C3—C3'—C42 | 2 (2) | C42'—C4—C42—C41' | −77 (3) |
C2—C3—C3'—C42 | 157.8 (18) | C3—C4—C42—C41' | −135.9 (19) |
C4—C3—C3'—C42 | 23.0 (11) | C10—C4—C42—C41' | 106.3 (19) |
C42'—C3—C3'—C4 | −21.5 (17) | C41—C4—C42—C41' | −19.3 (19) |
C2—C3—C3'—C4 | 134.8 (8) | C3'—C4—C42—C41' | −157 (2) |
C42'—C3—C3'—C2 | −156.3 (15) | C42'—C4—C42—C3' | 81 (2) |
C4—C3—C3'—C2 | −134.8 (8) | C3—C4—C42—C3' | 21.4 (11) |
O2—C2—C3'—C42 | 169 (4) | C10—C4—C42—C3' | −96.4 (11) |
O1—C2—C3'—C42 | 36 (4) | C41—C4—C42—C3' | 138.0 (12) |
C3—C2—C3'—C42 | −73 (4) | C41'—C4—C42—C3' | 157 (2) |
O2—C2—C3'—C3 | −118.1 (6) | C4—C41—C42'—C3 | 22 (2) |
O1—C2—C3'—C3 | 109.1 (7) | C41'—C41—C42'—C3 | −3 (3) |
O2—C2—C3'—C4 | −156.7 (9) | C41'—C41—C42'—C4 | −25.5 (15) |
O1—C2—C3'—C4 | 70.6 (12) | C2—C3—C42'—C41 | −107 (4) |
C3—C2—C3'—C4 | −38.6 (7) | C3'—C3—C42'—C41 | −1 (3) |
C2—C3—C4—C42' | 155.6 (15) | C4—C3—C42'—C41 | −23 (2) |
C3'—C3—C4—C42' | −159.5 (17) | C2—C3—C42'—C4 | −84 (4) |
C42'—C3—C4—C10 | −101.9 (14) | C3'—C3—C42'—C4 | 21.8 (17) |
C2—C3—C4—C10 | 53.6 (6) | C3—C4—C42'—C41 | 159 (2) |
C3'—C3—C4—C10 | 98.6 (10) | C10—C4—C42'—C41 | −102.9 (14) |
C42'—C3—C4—C41 | 16.9 (17) | C42—C4—C42'—C41 | 80 (2) |
C2—C3—C4—C41 | 172.5 (9) | C41'—C4—C42'—C41 | 35 (2) |
C3'—C3—C4—C41 | −142.5 (13) | C3'—C4—C42'—C41 | 140.7 (15) |
C42'—C3—C4—C42 | 138.4 (15) | C10—C4—C42'—C3 | 98.0 (9) |
C2—C3—C4—C42 | −66.0 (6) | C41—C4—C42'—C3 | −159 (2) |
C3'—C3—C4—C42 | −21.0 (10) | C42—C4—C42'—C3 | −79 (2) |
C42'—C3—C4—C41' | 101 (2) | C41'—C4—C42'—C3 | −124.3 (16) |
C2—C3—C4—C41' | −103.0 (18) | C3'—C4—C42'—C3 | −18.4 (16) |
C3'—C3—C4—C41' | −58 (2) | C10—C5—C6—O6 | 178.8 (3) |
C42'—C3—C4—C3' | 159.5 (17) | C51—C5—C6—O6 | −2.9 (4) |
C2—C3—C4—C3' | −45.0 (10) | C10—C5—C6—C7 | −0.6 (4) |
C42—C3'—C4—C42' | −138.0 (15) | C51—C5—C6—C7 | 177.8 (3) |
C3—C3'—C4—C42' | 17.9 (15) | O6—C6—C7—C8 | 178.9 (3) |
C2—C3'—C4—C42' | 55.4 (18) | C5—C6—C7—C8 | −1.8 (4) |
C42—C3'—C4—C3 | −156.0 (11) | O6—C6—C7—C71 | 1.0 (4) |
C2—C3'—C4—C3 | 37.5 (9) | C5—C6—C7—C71 | −179.7 (3) |
C42—C3'—C4—C10 | 103.6 (7) | C6—C7—C8—C9 | 1.3 (4) |
C3—C3'—C4—C10 | −100.4 (7) | C71—C7—C8—C9 | 179.2 (3) |
C2—C3'—C4—C10 | −62.9 (13) | C6—C7—C8—C81 | −178.8 (3) |
C42—C3'—C4—C41 | −84 (2) | C71—C7—C8—C81 | −1.0 (5) |
C3—C3'—C4—C41 | 72 (2) | C7—C8—C9—C10 | 1.6 (5) |
C2—C3'—C4—C41 | 109.1 (18) | C81—C8—C9—C10 | −178.3 (3) |
C3—C3'—C4—C42 | 156.0 (11) | C7—C8—C9—O1 | −176.5 (3) |
C2—C3'—C4—C42 | −166.5 (17) | C81—C8—C9—O1 | 3.6 (4) |
C42—C3'—C4—C41' | −14.1 (14) | C2—O1—C9—C8 | −169.4 (3) |
C3—C3'—C4—C41' | 141.9 (13) | C2—O1—C9—C10 | 12.5 (5) |
C2—C3'—C4—C41' | 179.4 (16) | C8—C9—C10—C5 | −3.9 (5) |
C3—C4—C41—C42' | −17.7 (18) | O1—C9—C10—C5 | 174.0 (3) |
C10—C4—C41—C42' | 98.1 (16) | C8—C9—C10—C4 | 178.3 (3) |
C42—C4—C41—C42' | −137.2 (16) | O1—C9—C10—C4 | −3.8 (5) |
C41'—C4—C41—C42' | −150 (2) | C6—C5—C10—C9 | 3.3 (4) |
C3'—C4—C41—C42' | −74 (3) | C51—C5—C10—C9 | −174.9 (3) |
C42'—C4—C41—C41' | 150 (2) | C6—C5—C10—C4 | −179.1 (3) |
C3—C4—C41—C41' | 131.8 (12) | C51—C5—C10—C4 | 2.7 (5) |
C10—C4—C41—C41' | −112.4 (13) | C42'—C4—C10—C9 | −86.5 (14) |
C42—C4—C41—C41' | 12.4 (12) | C3—C4—C10—C9 | −27.9 (5) |
C3'—C4—C41—C41' | 76 (2) | C41—C4—C10—C9 | −142.3 (9) |
C42'—C4—C41'—C42 | 134.1 (19) | C42—C4—C10—C9 | 91.5 (5) |
C3—C4—C41'—C42 | 64 (2) | C41'—C4—C10—C9 | 133.5 (14) |
C10—C4—C41'—C42 | −90.7 (17) | C3'—C4—C10—C9 | 32.4 (12) |
C41—C4—C41'—C42 | 161.7 (18) | C42'—C4—C10—C5 | 95.9 (14) |
C3'—C4—C41'—C42 | 18.7 (18) | C3—C4—C10—C5 | 154.5 (4) |
C42'—C4—C41'—C41 | −27.6 (18) | C41—C4—C10—C5 | 40.1 (9) |
C3—C4—C41'—C41 | −97.2 (14) | C42—C4—C10—C5 | −86.1 (6) |
C10—C4—C41'—C41 | 107.6 (9) | C41'—C4—C10—C5 | −44.1 (15) |
C42—C4—C41'—C41 | −161.7 (18) | C3'—C4—C10—C5 | −145.2 (12) |
C3'—C4—C41'—C41 | −143.0 (11) | | |