Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010100110X/bk1584sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010100110X/bk1584Isup2.hkl |
CCDC reference: 163945
Data collection: Diffractometer Control Software (Enraf-Nonius, 1988); cell refinement: Diffractometer Control Software; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C16H23NO4 | F(000) = 316 |
Mr = 293.35 | Dx = 1.180 Mg m−3 |
Triclinic, P1 | Melting point = 349–350 K |
a = 9.273 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.333 (3) Å | Cell parameters from 25 reflections |
c = 10.372 (4) Å | θ = 15.0–18.0° |
α = 94.16 (2)° | µ = 0.08 mm−1 |
β = 112.17 (2)° | T = 293 K |
γ = 93.09 (2)° | Plate, colorless |
V = 825.9 (4) Å3 | 0.49 × 0.33 × 0.17 mm |
Z = 2 |
CAD4 diffractometer | 2312 reflections with I > 2σ(I) |
Radiation source: normal focus Philips Mo tube | Rint = 0.007 |
Equatorial mounted graphite monochromator | θmax = 25.0°, θmin = 2.1° |
data from ω/2θ_scans | h = 0→11 |
Absorption correction: empirical (using intensity measurements), ψ scan (North et al., 1968) | k = −11→11 |
Tmin = 0.943, Tmax = 0.986 | l = −12→12 |
3043 measured reflections | 3 standard reflections every 60 min |
2846 independent reflections | intensity decay: not applied (less than 0.5) |
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)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.034P)2 + 0.4831P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
2846 reflections | Δρmax = 0.22 e Å−3 |
195 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.249 (9) |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.1726 (2) | 0.91661 (17) | 1.14755 (18) | 0.0450 (4) | |
H1N | 0.093 (3) | 0.940 (2) | 1.150 (2) | 0.059 (7)* | |
O1 | 0.16959 (16) | 0.94942 (14) | 0.88954 (15) | 0.0505 (4) | |
C1 | 0.1747 (3) | 1.1380 (2) | 0.7463 (2) | 0.0540 (5) | |
O2 | 0.2947 (2) | 0.75086 (17) | 0.8951 (2) | 0.0824 (6) | |
C2 | 0.0357 (3) | 1.1711 (3) | 0.6479 (3) | 0.0698 (7) | |
H2A | −0.0404 | 1.0977 | 0.5962 | 0.084* | |
O3 | 0.42378 (17) | 0.99491 (16) | 1.20007 (18) | 0.0646 (5) | |
C3 | 0.0089 (4) | 1.3137 (4) | 0.6256 (3) | 0.0881 (9) | |
H3A | −0.0849 | 1.3355 | 0.5585 | 0.106* | |
O4 | 0.27024 (16) | 1.11710 (14) | 1.28722 (15) | 0.0546 (4) | |
C4 | 0.1189 (5) | 1.4214 (3) | 0.7011 (4) | 0.0908 (10) | |
H4A | 0.1001 | 1.5168 | 0.6856 | 0.109* | |
C5 | 0.2563 (4) | 1.3908 (3) | 0.7994 (4) | 0.0835 (9) | |
H5A | 0.3311 | 1.4652 | 0.8514 | 0.100* | |
C6 | 0.2848 (3) | 1.2499 (3) | 0.8218 (3) | 0.0670 (7) | |
H6A | 0.3794 | 1.2296 | 0.8888 | 0.080* | |
C7 | 0.2067 (3) | 0.9854 (3) | 0.7703 (3) | 0.0729 (7) | |
H7A | 0.1432 | 0.9219 | 0.6877 | 0.088* | |
H7B | 0.3159 | 0.9734 | 0.7893 | 0.088* | |
C8 | 0.2225 (2) | 0.8268 (2) | 0.9414 (2) | 0.0483 (5) | |
C9 | 0.1714 (2) | 0.78836 (19) | 1.0587 (2) | 0.0428 (5) | |
C10 | 0.0028 (2) | 0.7213 (2) | 0.9897 (2) | 0.0548 (5) | |
H10A | −0.0621 | 0.7900 | 0.9362 | 0.082* | |
H10B | −0.0337 | 0.6948 | 1.0605 | 0.082* | |
H10C | −0.0018 | 0.6371 | 0.9289 | 0.082* | |
C11 | 0.2745 (3) | 0.6788 (2) | 1.1428 (3) | 0.0602 (6) | |
H11A | 0.3805 | 0.7207 | 1.1860 | 0.090* | |
H11B | 0.2694 | 0.5948 | 1.0816 | 0.090* | |
H11C | 0.2383 | 0.6520 | 1.2138 | 0.090* | |
C12 | 0.3008 (2) | 1.0093 (2) | 1.2112 (2) | 0.0452 (5) | |
C13 | 0.3860 (3) | 1.2415 (2) | 1.3573 (2) | 0.0572 (6) | |
C14 | 0.4277 (3) | 1.3174 (2) | 1.2519 (3) | 0.0650 (6) | |
H14A | 0.4859 | 1.2569 | 1.2143 | 0.097* | |
H14C | 0.4901 | 1.4060 | 1.2963 | 0.097* | |
H14B | 0.3338 | 1.3380 | 1.1776 | 0.097* | |
C15 | 0.2952 (4) | 1.3352 (3) | 1.4188 (3) | 0.0945 (10) | |
H15A | 0.2066 | 1.3647 | 1.3446 | 0.142* | |
H15C | 0.3614 | 1.4188 | 1.4722 | 0.142* | |
H15B | 0.2601 | 1.2815 | 1.4786 | 0.142* | |
C16 | 0.5275 (4) | 1.1923 (3) | 1.4696 (3) | 0.0987 (11) | |
H16A | 0.5825 | 1.1337 | 1.4270 | 0.148* | |
H16B | 0.4947 | 1.1372 | 1.5299 | 0.148* | |
H16C | 0.5952 | 1.2750 | 1.5235 | 0.148* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0408 (9) | 0.0415 (9) | 0.0544 (11) | −0.0010 (7) | 0.0220 (8) | −0.0028 (7) |
O1 | 0.0592 (9) | 0.0484 (8) | 0.0563 (9) | 0.0122 (6) | 0.0338 (7) | 0.0120 (6) |
C1 | 0.0664 (14) | 0.0560 (12) | 0.0548 (13) | 0.0094 (10) | 0.0388 (11) | 0.0119 (10) |
O2 | 0.1197 (15) | 0.0545 (10) | 0.1135 (15) | 0.0291 (10) | 0.0860 (13) | 0.0162 (9) |
C2 | 0.0708 (16) | 0.0865 (18) | 0.0573 (15) | 0.0013 (13) | 0.0311 (13) | 0.0077 (13) |
O3 | 0.0413 (8) | 0.0562 (9) | 0.0922 (12) | −0.0007 (6) | 0.0243 (8) | −0.0076 (8) |
C3 | 0.089 (2) | 0.117 (3) | 0.0771 (19) | 0.0443 (19) | 0.0433 (17) | 0.0433 (19) |
O4 | 0.0583 (9) | 0.0465 (8) | 0.0587 (9) | −0.0080 (6) | 0.0269 (7) | −0.0109 (7) |
C4 | 0.131 (3) | 0.0698 (18) | 0.111 (3) | 0.0330 (19) | 0.083 (2) | 0.0346 (18) |
C5 | 0.105 (2) | 0.0640 (16) | 0.105 (2) | −0.0095 (16) | 0.070 (2) | 0.0006 (15) |
C6 | 0.0624 (14) | 0.0782 (17) | 0.0705 (16) | 0.0043 (12) | 0.0364 (13) | 0.0103 (13) |
C7 | 0.109 (2) | 0.0633 (15) | 0.0740 (17) | 0.0187 (14) | 0.0625 (16) | 0.0154 (12) |
C8 | 0.0527 (11) | 0.0377 (10) | 0.0596 (13) | 0.0029 (9) | 0.0282 (10) | 0.0006 (9) |
C9 | 0.0428 (10) | 0.0365 (9) | 0.0491 (11) | 0.0002 (8) | 0.0184 (9) | 0.0013 (8) |
C10 | 0.0494 (12) | 0.0471 (12) | 0.0648 (14) | −0.0064 (9) | 0.0208 (10) | −0.0004 (10) |
C11 | 0.0645 (14) | 0.0486 (12) | 0.0653 (14) | 0.0116 (10) | 0.0205 (11) | 0.0111 (10) |
C12 | 0.0468 (11) | 0.0401 (10) | 0.0466 (11) | 0.0010 (8) | 0.0160 (9) | 0.0039 (8) |
C13 | 0.0650 (14) | 0.0449 (11) | 0.0523 (13) | −0.0097 (10) | 0.0161 (11) | −0.0068 (9) |
C14 | 0.0674 (15) | 0.0500 (12) | 0.0749 (16) | −0.0044 (11) | 0.0259 (12) | 0.0052 (11) |
C15 | 0.117 (2) | 0.0716 (17) | 0.103 (2) | −0.0237 (16) | 0.063 (2) | −0.0384 (16) |
C16 | 0.106 (2) | 0.0754 (18) | 0.0682 (18) | −0.0176 (16) | −0.0151 (16) | 0.0042 (14) |
N1—C12 | 1.346 (2) | C7—H7B | 0.9700 |
N1—C9 | 1.454 (2) | C8—C9 | 1.521 (3) |
N1—H1N | 0.80 (2) | C9—C11 | 1.525 (3) |
O1—C8 | 1.338 (2) | C9—C10 | 1.528 (3) |
O1—C7 | 1.459 (3) | C10—H10A | 0.9600 |
C1—C2 | 1.377 (3) | C10—H10B | 0.9600 |
C1—C6 | 1.382 (3) | C10—H10C | 0.9600 |
C1—C7 | 1.489 (3) | C11—H11A | 0.9600 |
O2—C8 | 1.194 (2) | C11—H11B | 0.9600 |
C2—C3 | 1.387 (4) | C11—H11C | 0.9600 |
C2—H2A | 0.9300 | C13—C14 | 1.500 (3) |
O3—C12 | 1.202 (2) | C13—C16 | 1.509 (4) |
C3—C4 | 1.355 (4) | C13—C15 | 1.511 (3) |
C3—H3A | 0.9300 | C14—H14A | 0.9600 |
O4—C12 | 1.341 (2) | C14—H14C | 0.9600 |
O4—C13 | 1.477 (2) | C14—H14B | 0.9600 |
C4—C5 | 1.359 (4) | C15—H15A | 0.9600 |
C4—H4A | 0.9300 | C15—H15C | 0.9600 |
C5—C6 | 1.374 (4) | C15—H15B | 0.9600 |
C5—H5A | 0.9300 | C16—H16A | 0.9600 |
C6—H6A | 0.9300 | C16—H16B | 0.9600 |
C7—H7A | 0.9700 | C16—H16C | 0.9600 |
C12—N1—C9 | 122.40 (17) | C9—C10—H10B | 109.5 |
C12—N1—H1N | 117.6 (17) | H10A—C10—H10B | 109.5 |
C9—N1—H1N | 119.4 (17) | C9—C10—H10C | 109.5 |
C8—O1—C7 | 115.00 (16) | H10A—C10—H10C | 109.5 |
C2—C1—C6 | 118.3 (2) | H10B—C10—H10C | 109.5 |
C2—C1—C7 | 121.0 (2) | C9—C11—H11A | 109.5 |
C6—C1—C7 | 120.6 (2) | C9—C11—H11B | 109.5 |
C1—C2—C3 | 120.2 (3) | H11A—C11—H11B | 109.5 |
C1—C2—H2A | 119.9 | C9—C11—H11C | 109.5 |
C3—C2—H2A | 119.9 | H11A—C11—H11C | 109.5 |
C4—C3—C2 | 120.3 (3) | H11B—C11—H11C | 109.5 |
C4—C3—H3A | 119.9 | O3—C12—O4 | 126.05 (18) |
C2—C3—H3A | 119.9 | O3—C12—N1 | 123.80 (19) |
C12—O4—C13 | 121.49 (16) | O4—C12—N1 | 110.15 (17) |
C3—C4—C5 | 120.4 (3) | O4—C13—C14 | 110.34 (17) |
C3—C4—H4A | 119.8 | O4—C13—C16 | 109.96 (18) |
C5—C4—H4A | 119.8 | C14—C13—C16 | 112.3 (2) |
C4—C5—C6 | 119.9 (3) | O4—C13—C15 | 101.63 (18) |
C4—C5—H5A | 120.0 | C14—C13—C15 | 110.5 (2) |
C6—C5—H5A | 120.0 | C16—C13—C15 | 111.7 (2) |
C5—C6—C1 | 120.9 (3) | C13—C14—H14A | 109.5 |
C5—C6—H6A | 119.6 | C13—C14—H14C | 109.5 |
C1—C6—H6A | 119.6 | H14A—C14—H14C | 109.5 |
O1—C7—C1 | 108.56 (17) | C13—C14—H14B | 109.5 |
O1—C7—H7A | 110.0 | H14A—C14—H14B | 109.5 |
C1—C7—H7A | 110.0 | H14C—C14—H14B | 109.5 |
O1—C7—H7B | 110.0 | C13—C15—H15A | 109.5 |
C1—C7—H7B | 110.0 | C13—C15—H15C | 109.5 |
H7A—C7—H7B | 108.4 | H15A—C15—H15C | 109.5 |
O2—C8—O1 | 123.5 (2) | C13—C15—H15B | 109.5 |
O2—C8—C9 | 123.25 (19) | H15A—C15—H15B | 109.5 |
O1—C8—C9 | 113.11 (16) | H15C—C15—H15B | 109.5 |
N1—C9—C8 | 111.10 (15) | C13—C16—H16A | 109.5 |
N1—C9—C11 | 111.53 (17) | C13—C16—H16B | 109.5 |
C8—C9—C11 | 110.15 (17) | H16A—C16—H16B | 109.5 |
N1—C9—C10 | 107.66 (16) | C13—C16—H16C | 109.5 |
C8—C9—C10 | 106.85 (17) | H16A—C16—H16C | 109.5 |
C11—C9—C10 | 109.39 (16) | H16B—C16—H16C | 109.5 |
C9—C10—H10A | 109.5 |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register