Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801006328/ob6034sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801006328/ob6034Isup2.hkl |
CCDC reference: 170289
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.058
- wR factor = 0.155
- Data-to-parameter ratio = 16.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
C17H27NO | Z = 2 |
Mr = 261.40 | F(000) = 288 |
Triclinic, P1 | Dx = 1.086 Mg m−3 |
a = 6.2854 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.626 (3) Å | Cell parameters from 3312 reflections |
c = 15.318 (5) Å | θ = 1.4–25.0° |
α = 97.391 (6)° | µ = 0.07 mm−1 |
β = 97.498 (6)° | T = 293 K |
γ = 100.559 (7)° | Prism, colorless |
V = 799.5 (4) Å3 | 0.25 × 0.20 × 0.20 mm |
Bruker SMART 1000 diffractometer | 1219 reflections with I > 2σ(I) |
ω scans | Rint = 0.040 |
Absorption correction: multi-scan [SAINT (Bruker 1998) and SADABS (Sheldrick, 1997)] | θmax = 25.0° |
Tmin = 0.984, Tmax = 0.987 | h = −6→7 |
3376 measured reflections | k = −7→10 |
2818 independent reflections | l = −18→18 |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.058 | w = 1/[σ2(Fo2) + (0.0528P)2 + 0.0223P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.155 | (Δ/σ)max = 0.022 |
S = 0.99 | Δρmax = 0.16 e Å−3 |
2818 reflections | Δρmin = −0.18 e Å−3 |
172 parameters |
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. Full-MATRIX |
x | y | z | Uiso*/Ueq | ||
N1 | −0.0386 (4) | 0.3200 (3) | 0.16721 (17) | 0.0448 (7) | |
O1 | 0.2393 (3) | 0.5997 (2) | 0.21525 (14) | 0.0541 (7) | |
H1A | 0.1197 | 0.5412 | 0.1958 | 0.081* | |
C1 | 0.0702 (5) | 0.2173 (4) | 0.1130 (2) | 0.0519 (9) | |
H1B | 0.0198 | 0.1071 | 0.1202 | 0.062* | |
H1C | 0.2270 | 0.2456 | 0.1333 | 0.062* | |
C2 | 0.0232 (5) | 0.2334 (4) | 0.0156 (2) | 0.0619 (10) | |
H2A | 0.0923 | 0.1605 | −0.0191 | 0.074* | |
H2B | 0.0857 | 0.3412 | 0.0078 | 0.074* | |
C3 | −0.2215 (5) | 0.1971 (5) | −0.0183 (2) | 0.0692 (11) | |
H3A | −0.2479 | 0.2208 | −0.0785 | 0.083* | |
H3B | −0.2809 | 0.0847 | −0.0195 | 0.083* | |
C4 | −0.3338 (5) | 0.2974 (5) | 0.0424 (2) | 0.0692 (11) | |
H4A | −0.2904 | 0.4088 | 0.0361 | 0.083* | |
H4B | −0.4913 | 0.2658 | 0.0243 | 0.083* | |
C5 | −0.2765 (5) | 0.2791 (4) | 0.1390 (2) | 0.0589 (10) | |
H5A | −0.3457 | 0.3485 | 0.1761 | 0.071* | |
H5B | −0.3316 | 0.1699 | 0.1466 | 0.071* | |
C6 | 0.0165 (5) | 0.3119 (4) | 0.2623 (2) | 0.0502 (9) | |
H6A | −0.0109 | 0.2009 | 0.2707 | 0.060* | |
H6B | −0.0792 | 0.3650 | 0.2949 | 0.060* | |
C7 | 0.2521 (5) | 0.3879 (4) | 0.3008 (2) | 0.0400 (8) | |
C8 | 0.3497 (5) | 0.5335 (4) | 0.2794 (2) | 0.0412 (8) | |
C9 | 0.5594 (5) | 0.6144 (4) | 0.32101 (19) | 0.0410 (8) | |
C10 | 0.6646 (5) | 0.5395 (4) | 0.3834 (2) | 0.0448 (9) | |
H10A | 0.8031 | 0.5914 | 0.4129 | 0.054* | |
C11 | 0.5767 (5) | 0.3919 (4) | 0.40477 (19) | 0.0424 (8) | |
C12 | 0.3690 (5) | 0.3189 (4) | 0.3625 (2) | 0.0470 (9) | |
H12A | 0.3054 | 0.2204 | 0.3758 | 0.056* | |
C13 | 0.7032 (5) | 0.3160 (4) | 0.4718 (2) | 0.0651 (11) | |
H13A | 0.6169 | 0.2151 | 0.4779 | 0.098* | |
H13B | 0.7364 | 0.3848 | 0.5283 | 0.098* | |
H13C | 0.8372 | 0.2996 | 0.4518 | 0.098* | |
C14 | 0.6678 (5) | 0.7764 (4) | 0.2997 (2) | 0.0471 (9) | |
C15 | 0.8877 (6) | 0.8454 (4) | 0.3604 (2) | 0.0823 (13) | |
H15A | 0.9841 | 0.7717 | 0.3540 | 0.123* | |
H15B | 0.8642 | 0.8628 | 0.4213 | 0.123* | |
H15C | 0.9525 | 0.9450 | 0.3440 | 0.123* | |
C16 | 0.7130 (5) | 0.7574 (4) | 0.2037 (2) | 0.0677 (11) | |
H16A | 0.5778 | 0.7155 | 0.1638 | 0.102* | |
H16B | 0.8113 | 0.6852 | 0.1967 | 0.102* | |
H16C | 0.7783 | 0.8595 | 0.1904 | 0.102* | |
C17 | 0.5191 (5) | 0.8979 (4) | 0.3124 (2) | 0.0701 (11) | |
H17A | 0.3806 | 0.8586 | 0.2743 | 0.105* | |
H17B | 0.5876 | 0.9978 | 0.2974 | 0.105* | |
H17C | 0.4962 | 0.9132 | 0.3734 | 0.105* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0307 (16) | 0.0490 (18) | 0.0523 (18) | 0.0066 (13) | 0.0065 (12) | 0.0013 (13) |
O1 | 0.0441 (14) | 0.0503 (15) | 0.0651 (16) | 0.0051 (12) | −0.0010 (11) | 0.0152 (12) |
C1 | 0.044 (2) | 0.061 (2) | 0.050 (2) | 0.0112 (19) | 0.0068 (16) | 0.0048 (18) |
C2 | 0.050 (2) | 0.075 (3) | 0.057 (2) | 0.008 (2) | 0.0091 (18) | 0.0027 (19) |
C3 | 0.053 (2) | 0.092 (3) | 0.055 (2) | 0.004 (2) | −0.0031 (19) | 0.013 (2) |
C4 | 0.043 (2) | 0.081 (3) | 0.082 (3) | 0.012 (2) | 0.000 (2) | 0.017 (2) |
C5 | 0.038 (2) | 0.071 (3) | 0.065 (3) | 0.0091 (19) | 0.0048 (17) | 0.009 (2) |
C6 | 0.049 (2) | 0.056 (2) | 0.043 (2) | 0.0032 (18) | 0.0107 (16) | 0.0027 (17) |
C7 | 0.041 (2) | 0.036 (2) | 0.040 (2) | 0.0015 (17) | 0.0099 (16) | 0.0009 (16) |
C8 | 0.042 (2) | 0.044 (2) | 0.038 (2) | 0.0163 (18) | 0.0016 (16) | 0.0060 (16) |
C9 | 0.042 (2) | 0.039 (2) | 0.039 (2) | 0.0054 (17) | 0.0051 (16) | 0.0008 (16) |
C10 | 0.041 (2) | 0.050 (2) | 0.040 (2) | 0.0076 (18) | 0.0016 (16) | 0.0017 (17) |
C11 | 0.049 (2) | 0.043 (2) | 0.0346 (19) | 0.0128 (18) | 0.0046 (16) | 0.0027 (16) |
C12 | 0.060 (2) | 0.040 (2) | 0.043 (2) | 0.0096 (19) | 0.0145 (18) | 0.0077 (17) |
C13 | 0.078 (3) | 0.071 (3) | 0.050 (2) | 0.025 (2) | 0.0013 (19) | 0.018 (2) |
C14 | 0.043 (2) | 0.043 (2) | 0.054 (2) | 0.0051 (18) | 0.0054 (17) | 0.0107 (17) |
C15 | 0.069 (3) | 0.063 (3) | 0.096 (3) | −0.017 (2) | −0.014 (2) | 0.017 (2) |
C16 | 0.062 (2) | 0.069 (3) | 0.077 (3) | 0.011 (2) | 0.018 (2) | 0.029 (2) |
C17 | 0.076 (3) | 0.043 (2) | 0.092 (3) | 0.011 (2) | 0.019 (2) | 0.008 (2) |
N1—C1 | 1.457 (4) | C8—C9 | 1.400 (4) |
N1—C5 | 1.464 (3) | C9—C10 | 1.385 (4) |
N1—C6 | 1.466 (4) | C9—C14 | 1.532 (4) |
O1—C8 | 1.372 (3) | C10—C11 | 1.389 (4) |
O1—H1A | 0.8200 | C10—H10A | 0.9300 |
C1—C2 | 1.512 (4) | C11—C12 | 1.376 (4) |
C1—H1B | 0.9700 | C11—C13 | 1.505 (4) |
C1—H1C | 0.9700 | C12—H12A | 0.9300 |
C2—C3 | 1.519 (4) | C13—H13A | 0.9600 |
C2—H2A | 0.9700 | C13—H13B | 0.9600 |
C2—H2B | 0.9700 | C13—H13C | 0.9600 |
C3—C4 | 1.516 (5) | C14—C16 | 1.527 (4) |
C3—H3A | 0.9700 | C14—C15 | 1.533 (4) |
C3—H3B | 0.9700 | C14—C17 | 1.538 (4) |
C4—C5 | 1.513 (4) | C15—H15A | 0.9600 |
C4—H4A | 0.9700 | C15—H15B | 0.9600 |
C4—H4B | 0.9700 | C15—H15C | 0.9600 |
C5—H5A | 0.9700 | C16—H16A | 0.9600 |
C5—H5B | 0.9700 | C16—H16B | 0.9600 |
C6—C7 | 1.513 (4) | C16—H16C | 0.9600 |
C6—H6A | 0.9700 | C17—H17A | 0.9600 |
C6—H6B | 0.9700 | C17—H17B | 0.9600 |
C7—C12 | 1.382 (4) | C17—H17C | 0.9600 |
C7—C8 | 1.392 (4) | ||
C1—N1—C5 | 110.9 (2) | O1—C8—C9 | 118.7 (3) |
C1—N1—C6 | 111.4 (2) | C7—C8—C9 | 121.7 (3) |
C5—N1—C6 | 110.5 (2) | C10—C9—C8 | 116.0 (3) |
C8—O1—H1A | 109.5 | C10—C9—C14 | 121.5 (3) |
N1—C1—C2 | 111.1 (3) | C8—C9—C14 | 122.5 (3) |
N1—C1—H1B | 109.4 | C9—C10—C11 | 124.3 (3) |
C2—C1—H1B | 109.4 | C9—C10—H10A | 117.9 |
N1—C1—H1C | 109.4 | C11—C10—H10A | 117.9 |
C2—C1—H1C | 109.4 | C12—C11—C10 | 117.1 (3) |
H1B—C1—H1C | 108.0 | C12—C11—C13 | 121.6 (3) |
C1—C2—C3 | 111.4 (3) | C10—C11—C13 | 121.3 (3) |
C1—C2—H2A | 109.4 | C11—C12—C7 | 121.9 (3) |
C3—C2—H2A | 109.4 | C11—C12—H12A | 119.1 |
C1—C2—H2B | 109.4 | C7—C12—H12A | 119.1 |
C3—C2—H2B | 109.4 | C11—C13—H13A | 109.5 |
H2A—C2—H2B | 108.0 | C11—C13—H13B | 109.5 |
C4—C3—C2 | 109.5 (3) | H13A—C13—H13B | 109.5 |
C4—C3—H3A | 109.8 | C11—C13—H13C | 109.5 |
C2—C3—H3A | 109.8 | H13A—C13—H13C | 109.5 |
C4—C3—H3B | 109.8 | H13B—C13—H13C | 109.5 |
C2—C3—H3B | 109.8 | C16—C14—C9 | 109.8 (3) |
H3A—C3—H3B | 108.2 | C16—C14—C15 | 107.4 (3) |
C5—C4—C3 | 111.9 (3) | C9—C14—C15 | 111.9 (3) |
C5—C4—H4A | 109.2 | C16—C14—C17 | 109.6 (3) |
C3—C4—H4A | 109.2 | C9—C14—C17 | 110.5 (3) |
C5—C4—H4B | 109.2 | C15—C14—C17 | 107.6 (3) |
C3—C4—H4B | 109.2 | C14—C15—H15A | 109.5 |
H4A—C4—H4B | 107.9 | C14—C15—H15B | 109.5 |
N1—C5—C4 | 110.5 (3) | H15A—C15—H15B | 109.5 |
N1—C5—H5A | 109.6 | C14—C15—H15C | 109.5 |
C4—C5—H5A | 109.6 | H15A—C15—H15C | 109.5 |
N1—C5—H5B | 109.6 | H15B—C15—H15C | 109.5 |
C4—C5—H5B | 109.6 | C14—C16—H16A | 109.5 |
H5A—C5—H5B | 108.1 | C14—C16—H16B | 109.5 |
N1—C6—C7 | 113.4 (2) | H16A—C16—H16B | 109.5 |
N1—C6—H6A | 108.9 | C14—C16—H16C | 109.5 |
C7—C6—H6A | 108.9 | H16A—C16—H16C | 109.5 |
N1—C6—H6B | 108.9 | H16B—C16—H16C | 109.5 |
C7—C6—H6B | 108.9 | C14—C17—H17A | 109.5 |
H6A—C6—H6B | 107.7 | C14—C17—H17B | 109.5 |
C12—C7—C8 | 119.0 (3) | H17A—C17—H17B | 109.5 |
C12—C7—C6 | 120.3 (3) | C14—C17—H17C | 109.5 |
C8—C7—C6 | 120.6 (3) | H17A—C17—H17C | 109.5 |
O1—C8—C7 | 119.5 (3) | H17B—C17—H17C | 109.5 |
C5—N1—C1—C2 | 59.8 (3) | C7—C8—C9—C10 | 1.1 (4) |
C6—N1—C1—C2 | −176.7 (3) | O1—C8—C9—C14 | 1.8 (4) |
N1—C1—C2—C3 | −56.6 (4) | C7—C8—C9—C14 | −178.7 (3) |
C1—C2—C3—C4 | 52.5 (4) | C8—C9—C10—C11 | 1.1 (4) |
C2—C3—C4—C5 | −52.9 (4) | C14—C9—C10—C11 | −179.1 (3) |
C1—N1—C5—C4 | −59.5 (4) | C9—C10—C11—C12 | −1.9 (5) |
C6—N1—C5—C4 | 176.5 (3) | C9—C10—C11—C13 | 178.5 (3) |
C3—C4—C5—N1 | 56.6 (4) | C10—C11—C12—C7 | 0.5 (4) |
C1—N1—C6—C7 | 69.3 (3) | C13—C11—C12—C7 | −179.9 (3) |
C5—N1—C6—C7 | −166.9 (3) | C8—C7—C12—C11 | 1.6 (4) |
N1—C6—C7—C12 | −141.2 (3) | C6—C7—C12—C11 | −174.2 (3) |
N1—C6—C7—C8 | 43.1 (4) | C10—C9—C14—C16 | 114.1 (3) |
C12—C7—C8—O1 | 177.0 (3) | C8—C9—C14—C16 | −66.0 (4) |
C6—C7—C8—O1 | −7.2 (4) | C10—C9—C14—C15 | −5.0 (4) |
C12—C7—C8—C9 | −2.4 (4) | C8—C9—C14—C15 | 174.9 (3) |
C6—C7—C8—C9 | 173.3 (3) | C10—C9—C14—C17 | −124.8 (3) |
O1—C8—C9—C10 | −178.4 (3) | C8—C9—C14—C17 | 55.0 (4) |
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