Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802008383/bt6145sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802008383/bt6145Isup2.hkl |
CCDC reference: 189382
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1988); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
C11H13NO | F(000) = 188 |
Mr = 175.22 | Dx = 1.245 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.7769 (4) Å | Cell parameters from 1140 reflections |
b = 6.2492 (3) Å | θ = 1.0–27.5° |
c = 9.6263 (5) Å | µ = 0.08 mm−1 |
β = 92.749 (2)° | T = 123 K |
V = 467.29 (4) Å3 | Needle, colourless |
Z = 2 | 0.60 × 0.10 × 0.04 mm |
Nonius KappaCCD diffractometer | 810 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.051 |
Graphite monochromator | θmax = 27.5°, θmin = 2.1° |
ω and φ scans | h = −9→10 |
6426 measured reflections | k = −8→8 |
1163 independent reflections | l = −12→12 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0488P)2] where P = (Fo2 + 2Fc2)/3 |
1163 reflections | (Δ/σ)max < 0.001 |
125 parameters | Δρmax = 0.18 e Å−3 |
1 restraint | Δρmin = −0.23 e Å−3 |
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. H on N refined isotropically. All others in calc positions and riding modes. The methyl groups were allowed to rotate but not to tip. Friedel pairs were merged for the final refinement. This made no significant change to the geometric parameters. 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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.7746 (2) | 0.3981 (3) | 0.50995 (17) | 0.0264 (5) | |
N1 | 0.6070 (3) | 0.8496 (4) | 0.9741 (2) | 0.0247 (6) | |
C1 | 0.6962 (3) | 0.7380 (5) | 1.0786 (2) | 0.0220 (6) | |
C2 | 0.7812 (3) | 0.5693 (4) | 1.0220 (3) | 0.0205 (6) | |
C3 | 0.7435 (3) | 0.5769 (5) | 0.8740 (2) | 0.0190 (6) | |
C4 | 0.6330 (3) | 0.7516 (4) | 0.8479 (2) | 0.0210 (6) | |
C5 | 0.5682 (3) | 0.8008 (5) | 0.7145 (3) | 0.0245 (7) | |
H5 | 0.4910 | 0.9170 | 0.6985 | 0.029* | |
C6 | 0.6196 (3) | 0.6756 (5) | 0.6066 (3) | 0.0267 (7) | |
H6 | 0.5774 | 0.7061 | 0.5145 | 0.032* | |
C7 | 0.7330 (3) | 0.5042 (4) | 0.6299 (3) | 0.0210 (7) | |
C8 | 0.7953 (3) | 0.4500 (4) | 0.7620 (2) | 0.0207 (7) | |
H8 | 0.8705 | 0.3315 | 0.7771 | 0.025* | |
C9 | 0.6912 (3) | 0.8130 (5) | 1.2249 (2) | 0.0272 (7) | |
H9A | 0.5716 | 0.8407 | 1.2474 | 0.041* | |
H9B | 0.7584 | 0.9449 | 1.2364 | 0.041* | |
H9C | 0.7401 | 0.7027 | 1.2875 | 0.041* | |
C10 | 0.8945 (3) | 0.4101 (5) | 1.0966 (3) | 0.0287 (7) | |
H10A | 0.8855 | 0.4275 | 1.1971 | 0.043* | |
H10B | 1.0140 | 0.4329 | 1.0723 | 0.043* | |
H10C | 0.8584 | 0.2652 | 1.0694 | 0.043* | |
C11 | 0.8822 (4) | 0.2142 (5) | 0.5252 (3) | 0.0333 (8) | |
H11A | 0.8252 | 0.1060 | 0.5806 | 0.050* | |
H11B | 0.9919 | 0.2547 | 0.5723 | 0.050* | |
H11C | 0.9035 | 0.1553 | 0.4332 | 0.050* | |
H1 | 0.528 (4) | 0.961 (6) | 0.985 (4) | 0.051 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0297 (10) | 0.0303 (12) | 0.0193 (10) | 0.0038 (10) | 0.0020 (8) | −0.0053 (9) |
N1 | 0.0277 (13) | 0.0252 (15) | 0.0210 (13) | 0.0070 (12) | −0.0004 (10) | 0.0003 (11) |
C1 | 0.0196 (13) | 0.0269 (16) | 0.0192 (15) | −0.0030 (13) | −0.0013 (11) | −0.0008 (13) |
C2 | 0.0199 (13) | 0.0202 (15) | 0.0212 (14) | −0.0005 (13) | −0.0007 (10) | 0.0013 (13) |
C3 | 0.0168 (12) | 0.0210 (14) | 0.0191 (14) | −0.0031 (12) | −0.0005 (10) | 0.0034 (13) |
C4 | 0.0211 (13) | 0.0229 (16) | 0.0192 (15) | 0.0001 (14) | 0.0019 (11) | −0.0005 (13) |
C5 | 0.0265 (15) | 0.0231 (16) | 0.0238 (15) | 0.0051 (14) | −0.0002 (12) | 0.0043 (13) |
C6 | 0.0259 (15) | 0.0339 (17) | 0.0199 (15) | −0.0008 (14) | −0.0023 (12) | 0.0017 (14) |
C7 | 0.0201 (13) | 0.0244 (16) | 0.0188 (15) | −0.0039 (14) | 0.0040 (11) | −0.0021 (13) |
C8 | 0.0173 (13) | 0.0254 (17) | 0.0195 (15) | −0.0003 (12) | 0.0008 (11) | 0.0000 (13) |
C9 | 0.0318 (15) | 0.0285 (16) | 0.0216 (14) | 0.0017 (14) | 0.0023 (12) | −0.0024 (13) |
C10 | 0.0311 (15) | 0.0300 (18) | 0.0247 (15) | 0.0063 (14) | −0.0014 (12) | −0.0011 (14) |
C11 | 0.0401 (17) | 0.0319 (19) | 0.0277 (16) | 0.0004 (16) | 0.0002 (13) | −0.0094 (15) |
O1—C7 | 1.383 (3) | C6—C7 | 1.399 (4) |
O1—C11 | 1.425 (3) | C6—H6 | 0.9500 |
N1—C1 | 1.383 (3) | C7—C8 | 1.381 (3) |
N1—C4 | 1.384 (3) | C8—H8 | 0.9500 |
N1—H1 | 0.94 (4) | C9—H9A | 0.9800 |
C1—C2 | 1.371 (4) | C9—H9B | 0.9800 |
C1—C9 | 1.487 (3) | C9—H9C | 0.9800 |
C2—C3 | 1.441 (4) | C10—H10A | 0.9800 |
C2—C10 | 1.490 (4) | C10—H10B | 0.9800 |
C3—C4 | 1.405 (3) | C10—H10C | 0.9800 |
C3—C8 | 1.412 (4) | C11—H11A | 0.9800 |
C4—C5 | 1.391 (3) | C11—H11B | 0.9800 |
C5—C6 | 1.375 (4) | C11—H11C | 0.9800 |
C5—H5 | 0.9500 | ||
C7—O1—C11 | 117.4 (2) | C8—C7—C6 | 121.8 (2) |
C1—N1—C4 | 109.0 (2) | O1—C7—C6 | 113.8 (2) |
C1—N1—H1 | 127 (2) | C7—C8—C3 | 117.7 (2) |
C4—N1—H1 | 123 (2) | C7—C8—H8 | 121.2 |
C2—C1—N1 | 109.5 (2) | C3—C8—H8 | 121.2 |
C2—C1—C9 | 130.8 (2) | C1—C9—H9A | 109.5 |
N1—C1—C9 | 119.7 (2) | C1—C9—H9B | 109.5 |
C1—C2—C3 | 106.8 (2) | H9A—C9—H9B | 109.5 |
C1—C2—C10 | 127.4 (2) | C1—C9—H9C | 109.5 |
C3—C2—C10 | 125.9 (2) | H9A—C9—H9C | 109.5 |
C4—C3—C8 | 119.6 (2) | H9B—C9—H9C | 109.5 |
C4—C3—C2 | 107.2 (2) | C2—C10—H10A | 109.5 |
C8—C3—C2 | 133.2 (2) | C2—C10—H10B | 109.5 |
N1—C4—C5 | 130.6 (2) | H10A—C10—H10B | 109.5 |
N1—C4—C3 | 107.5 (2) | C2—C10—H10C | 109.5 |
C5—C4—C3 | 121.9 (2) | H10A—C10—H10C | 109.5 |
C6—C5—C4 | 117.8 (3) | H10B—C10—H10C | 109.5 |
C6—C5—H5 | 121.1 | O1—C11—H11A | 109.5 |
C4—C5—H5 | 121.1 | O1—C11—H11B | 109.5 |
C5—C6—C7 | 121.2 (2) | H11A—C11—H11B | 109.5 |
C5—C6—H6 | 119.4 | O1—C11—H11C | 109.5 |
C7—C6—H6 | 119.4 | H11A—C11—H11C | 109.5 |
C8—C7—O1 | 124.5 (2) | H11B—C11—H11C | 109.5 |
C4—N1—C1—C2 | 0.5 (3) | C8—C3—C4—C5 | 1.9 (4) |
C4—N1—C1—C9 | 179.2 (2) | C2—C3—C4—C5 | −178.4 (2) |
N1—C1—C2—C3 | 0.2 (3) | N1—C4—C5—C6 | 178.8 (3) |
C9—C1—C2—C3 | −178.2 (3) | C3—C4—C5—C6 | −1.8 (4) |
N1—C1—C2—C10 | 179.0 (2) | C4—C5—C6—C7 | 0.1 (4) |
C9—C1—C2—C10 | 0.5 (4) | C11—O1—C7—C8 | 3.3 (4) |
C1—C2—C3—C4 | −0.9 (3) | C11—O1—C7—C6 | −176.7 (2) |
C10—C2—C3—C4 | −179.7 (2) | C5—C6—C7—C8 | 1.4 (4) |
C1—C2—C3—C8 | 178.8 (3) | C5—C6—C7—O1 | −178.6 (2) |
C10—C2—C3—C8 | 0.0 (5) | O1—C7—C8—C3 | 178.7 (2) |
C1—N1—C4—C5 | 178.4 (3) | C6—C7—C8—C3 | −1.3 (4) |
C1—N1—C4—C3 | −1.1 (3) | C4—C3—C8—C7 | −0.3 (4) |
C8—C3—C4—N1 | −178.6 (2) | C2—C3—C8—C7 | −180.0 (3) |
C2—C3—C4—N1 | 1.2 (3) |