Unnatural cyclic α-amino acids play an important role in the search for biologically active compounds and macromolecules. Enantiomers of natural amino acids with a
D configuration are not naturally encoded, but can be chemically synthesized. The crystal structures of two enantiomers obtained by a method of stereoselective synthesis, namely (5
R,8
S)-8-
tert-butyl-7-methoxy-8-methyl-9-oxa-6-azaspiro[4.5]decane-2,10-dione, (1), and (5
S,8
R)-8-
tert-butyl-7-methoxy-8-methyl-9-oxa-6-azaspiro[4.5]decane-2,10-dione, (2), both C
14H
21NO
4, were determined by X-ray diffraction. Both enantiomers crystallize isostructurally in the space group
P2
1, with one molecule in the asymmetric unit and with the same packing motif. The crystal structures are stabilized by C—H
O hydrogen bonds, resulting in the formation of chains along the [100] and [010] directions. The conformation of the 3,6-dihydro-2
H-1,4-oxazin-2-one fragment was compared with other crystal structures possessing this heterocyclic moiety. The comparison showed that the title compounds are not exceptional among structures containing the 3,6-dihydro-2
H-1,4-oxazin-2-one fragment. The planar moiety was more frequently observed in derivatives in which this fragment was not condensed with other rings.
Supporting information
CCDC references: 1556628; 1556627
Data collection: CrysAlis PRO (Rigaku OD, 2015) for (1); CrysAlis PRO (Agilent, 2014) for (2). Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for (1); CrysAlis PRO (Agilent, 2014) for (2). Data reduction: CrysAlis PRO (Rigaku OD, 2015) for (1); CrysAlis PRO (Agilent, 2014) for (2). For both compounds, program(s) used to refine structure: SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008) and SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
(1) (5
R,8
S)-8-
tert-Butyl-7-methoxy-8-methyl-9-oxa-6-azaspiro[4.5]decan-2,10-dione
top
Crystal data top
C14H21NO4 | F(000) = 288 |
Mr = 267.32 | Dx = 1.218 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: P 2yb | Cell parameters from 7013 reflections |
a = 8.7136 (2) Å | θ = 3.4–71.3° |
b = 6.3606 (2) Å | µ = 0.73 mm−1 |
c = 13.3613 (3) Å | T = 293 K |
β = 100.220 (2)° | Block, colourless |
V = 728.78 (3) Å3 | 0.3 × 0.2 × 0.15 mm |
Z = 2 | |
Data collection top
Rigaku Oxford Diffraction SuperNova Dual Source diffractometer with an
Atlas detector | 2784 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 2687 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.031 |
Detector resolution: 10.3756 pixels mm-1 | θmax = 71.3°, θmin = 3.4° |
ω scans | h = −10→10 |
Absorption correction: gaussian (CrysAlis PRO (Rigaku OD, 2015) | k = −7→7 |
Tmin = 0.67, Tmax = 0.789 | l = −16→16 |
9732 measured reflections | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0495P)2 + 0.0486P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.032 | (Δ/σ)max < 0.001 |
wR(F2) = 0.087 | Δρmax = 0.14 e Å−3 |
S = 1.04 | Δρmin = −0.12 e Å−3 |
2784 reflections | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
178 parameters | Extinction coefficient: 0.036 (4) |
1 restraint | Absolute structure: Flack x determined using 1165 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons & Flack, 2004) |
Hydrogen site location: inferred from neighbouring sites | Absolute structure parameter: 0.05 (9) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C8 | 0.7582 (2) | −0.0099 (3) | 0.77356 (13) | 0.0518 (4) | |
O9 | 0.91198 (16) | −0.1048 (2) | 0.80511 (11) | 0.0625 (4) | |
C10 | 1.0452 (2) | −0.0238 (3) | 0.78789 (14) | 0.0540 (4) | |
C5 | 1.04114 (19) | 0.1531 (3) | 0.71098 (12) | 0.0469 (4) | |
N6 | 0.88669 (16) | 0.2157 (2) | 0.65914 (10) | 0.0450 (3) | |
C7 | 0.76752 (19) | 0.1439 (3) | 0.68780 (12) | 0.0457 (4) | |
C12 | 0.6530 (3) | −0.1922 (5) | 0.73256 (19) | 0.0778 (7) | |
H12A | 0.6587 | −0.2993 | 0.7837 | 0.117* | |
H12B | 0.6863 | −0.2491 | 0.6734 | 0.117* | |
H12C | 0.5475 | −0.1434 | 0.7147 | 0.117* | |
C13 | 0.7148 (2) | 0.0970 (4) | 0.87027 (14) | 0.0623 (6) | |
C14 | 0.7210 (4) | −0.0686 (7) | 0.9554 (2) | 0.1028 (11) | |
H14A | 0.7022 | −0.0015 | 1.0164 | 0.154* | |
H14B | 0.822 | −0.1336 | 0.9679 | 0.154* | |
H14C | 0.6427 | −0.1737 | 0.9348 | 0.154* | |
C15 | 0.8297 (3) | 0.2731 (6) | 0.90700 (19) | 0.0885 (9) | |
H15A | 0.7987 | 0.3428 | 0.964 | 0.133* | |
H15B | 0.8306 | 0.3723 | 0.853 | 0.133* | |
H15C | 0.9322 | 0.215 | 0.9272 | 0.133* | |
C16 | 0.5514 (3) | 0.1913 (6) | 0.8486 (2) | 0.0871 (9) | |
H16A | 0.5449 | 0.2918 | 0.7945 | 0.131* | |
H16B | 0.5301 | 0.2599 | 0.9087 | 0.131* | |
H16C | 0.4764 | 0.0816 | 0.8292 | 0.131* | |
O7 | 0.62354 (14) | 0.1949 (3) | 0.63816 (9) | 0.0572 (4) | |
C11 | 0.6178 (2) | 0.3215 (4) | 0.54812 (15) | 0.0606 (5) | |
H11A | 0.6651 | 0.2462 | 0.4992 | 0.091* | |
H11B | 0.6734 | 0.4505 | 0.5656 | 0.091* | |
H11C | 0.5112 | 0.3523 | 0.5195 | 0.091* | |
O10 | 1.16585 (18) | −0.0998 (3) | 0.83021 (13) | 0.0809 (6) | |
C4 | 1.1303 (2) | 0.3520 (3) | 0.75557 (15) | 0.0578 (5) | |
H4A | 1.0647 | 0.4405 | 0.7895 | 0.069* | |
H4B | 1.2233 | 0.3146 | 0.8036 | 0.069* | |
C3 | 1.1724 (3) | 0.4627 (4) | 0.66307 (18) | 0.0701 (6) | |
H3A | 1.0942 | 0.567 | 0.6371 | 0.084* | |
H3B | 1.2728 | 0.5318 | 0.6804 | 0.084* | |
C2 | 1.1780 (2) | 0.2925 (4) | 0.58571 (15) | 0.0579 (5) | |
C1 | 1.1331 (2) | 0.0863 (4) | 0.62779 (14) | 0.0533 (4) | |
H1A | 1.2248 | 0.0053 | 0.6564 | 0.064* | |
H1B | 1.0687 | 0.0036 | 0.5755 | 0.064* | |
O2 | 1.2125 (2) | 0.3169 (4) | 0.50296 (14) | 0.0856 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C8 | 0.0493 (9) | 0.0616 (11) | 0.0453 (9) | −0.0009 (8) | 0.0106 (7) | 0.0078 (8) |
O9 | 0.0619 (8) | 0.0647 (9) | 0.0644 (8) | 0.0124 (7) | 0.0206 (6) | 0.0245 (7) |
C10 | 0.0542 (10) | 0.0616 (11) | 0.0472 (9) | 0.0104 (9) | 0.0117 (7) | 0.0076 (8) |
C5 | 0.0457 (8) | 0.0531 (10) | 0.0416 (8) | 0.0030 (7) | 0.0067 (6) | 0.0033 (7) |
N6 | 0.0459 (7) | 0.0483 (8) | 0.0401 (7) | 0.0012 (6) | 0.0058 (5) | 0.0033 (6) |
C7 | 0.0468 (9) | 0.0512 (10) | 0.0382 (8) | 0.0016 (7) | 0.0054 (6) | 0.0003 (7) |
C12 | 0.0902 (16) | 0.0731 (15) | 0.0710 (13) | −0.0245 (14) | 0.0168 (12) | 0.0070 (13) |
C13 | 0.0527 (9) | 0.0942 (16) | 0.0414 (8) | 0.0061 (11) | 0.0124 (7) | 0.0066 (10) |
C14 | 0.105 (2) | 0.149 (3) | 0.0607 (14) | 0.022 (2) | 0.0338 (14) | 0.0396 (18) |
C15 | 0.0818 (15) | 0.124 (2) | 0.0620 (13) | −0.0082 (16) | 0.0184 (11) | −0.0339 (15) |
C16 | 0.0619 (12) | 0.132 (3) | 0.0710 (14) | 0.0202 (15) | 0.0216 (10) | 0.0025 (16) |
O7 | 0.0456 (6) | 0.0755 (9) | 0.0488 (7) | 0.0002 (6) | 0.0041 (5) | 0.0097 (6) |
C11 | 0.0565 (10) | 0.0712 (13) | 0.0504 (10) | 0.0036 (10) | −0.0007 (8) | 0.0116 (10) |
O10 | 0.0643 (9) | 0.1032 (13) | 0.0752 (10) | 0.0257 (9) | 0.0124 (7) | 0.0369 (10) |
C4 | 0.0520 (9) | 0.0655 (13) | 0.0539 (10) | −0.0045 (9) | 0.0037 (7) | −0.0103 (9) |
C3 | 0.0709 (13) | 0.0628 (13) | 0.0773 (15) | −0.0144 (11) | 0.0149 (11) | −0.0001 (11) |
C2 | 0.0480 (9) | 0.0673 (12) | 0.0604 (11) | 0.0052 (9) | 0.0148 (8) | 0.0107 (10) |
C1 | 0.0525 (9) | 0.0604 (11) | 0.0482 (9) | 0.0062 (9) | 0.0125 (7) | 0.0028 (8) |
O2 | 0.0998 (12) | 0.0915 (12) | 0.0765 (10) | 0.0156 (11) | 0.0460 (9) | 0.0243 (10) |
Geometric parameters (Å, º) top
C8—O9 | 1.462 (2) | C15—H15A | 0.96 |
C8—C12 | 1.519 (3) | C15—H15B | 0.96 |
C8—C7 | 1.520 (2) | C15—H15C | 0.96 |
C8—C13 | 1.565 (3) | C16—H16A | 0.96 |
O9—C10 | 1.327 (3) | C16—H16B | 0.96 |
C10—O10 | 1.203 (2) | C16—H16C | 0.96 |
C10—C5 | 1.520 (3) | O7—C11 | 1.441 (2) |
C5—N6 | 1.456 (2) | C11—H11A | 0.96 |
C5—C1 | 1.541 (2) | C11—H11B | 0.96 |
C5—C4 | 1.548 (3) | C11—H11C | 0.96 |
N6—C7 | 1.255 (2) | C4—C3 | 1.523 (3) |
C7—O7 | 1.351 (2) | C4—H4A | 0.97 |
C12—H12A | 0.96 | C4—H4B | 0.97 |
C12—H12B | 0.96 | C3—C2 | 1.503 (3) |
C12—H12C | 0.96 | C3—H3A | 0.97 |
C13—C15 | 1.524 (4) | C3—H3B | 0.97 |
C13—C16 | 1.525 (3) | C2—O2 | 1.206 (2) |
C13—C14 | 1.544 (4) | C2—C1 | 1.506 (3) |
C14—H14A | 0.96 | C1—H1A | 0.97 |
C14—H14B | 0.96 | C1—H1B | 0.97 |
C14—H14C | 0.96 | | |
| | | |
O9—C8—C12 | 104.63 (19) | C13—C15—H15B | 109.5 |
O9—C8—C7 | 108.34 (14) | H15A—C15—H15B | 109.5 |
C12—C8—C7 | 109.20 (16) | C13—C15—H15C | 109.5 |
O9—C8—C13 | 106.55 (14) | H15A—C15—H15C | 109.5 |
C12—C8—C13 | 114.24 (17) | H15B—C15—H15C | 109.5 |
C7—C8—C13 | 113.32 (18) | C13—C16—H16A | 109.5 |
C10—O9—C8 | 125.09 (15) | C13—C16—H16B | 109.5 |
O10—C10—O9 | 118.72 (19) | H16A—C16—H16B | 109.5 |
O10—C10—C5 | 121.94 (18) | C13—C16—H16C | 109.5 |
O9—C10—C5 | 119.24 (16) | H16A—C16—H16C | 109.5 |
N6—C5—C10 | 115.66 (15) | H16B—C16—H16C | 109.5 |
N6—C5—C1 | 106.71 (13) | C7—O7—C11 | 115.83 (14) |
C10—C5—C1 | 109.34 (15) | O7—C11—H11A | 109.5 |
N6—C5—C4 | 108.54 (15) | O7—C11—H11B | 109.5 |
C10—C5—C4 | 113.26 (15) | H11A—C11—H11B | 109.5 |
C1—C5—C4 | 102.30 (15) | O7—C11—H11C | 109.5 |
C7—N6—C5 | 120.02 (15) | H11A—C11—H11C | 109.5 |
N6—C7—O7 | 120.63 (16) | H11B—C11—H11C | 109.5 |
N6—C7—C8 | 128.47 (15) | C3—C4—C5 | 104.02 (15) |
O7—C7—C8 | 110.85 (14) | C3—C4—H4A | 111 |
C8—C12—H12A | 109.5 | C5—C4—H4A | 111 |
C8—C12—H12B | 109.5 | C3—C4—H4B | 111 |
H12A—C12—H12B | 109.5 | C5—C4—H4B | 111 |
C8—C12—H12C | 109.5 | H4A—C4—H4B | 109 |
H12A—C12—H12C | 109.5 | C2—C3—C4 | 105.49 (19) |
H12B—C12—H12C | 109.5 | C2—C3—H3A | 110.6 |
C15—C13—C16 | 108.0 (3) | C4—C3—H3A | 110.6 |
C15—C13—C14 | 109.2 (2) | C2—C3—H3B | 110.6 |
C16—C13—C14 | 108.5 (2) | C4—C3—H3B | 110.6 |
C15—C13—C8 | 110.12 (16) | H3A—C3—H3B | 108.8 |
C16—C13—C8 | 111.65 (17) | O2—C2—C3 | 125.6 (2) |
C14—C13—C8 | 109.3 (2) | O2—C2—C1 | 125.3 (2) |
C13—C14—H14A | 109.5 | C3—C2—C1 | 109.15 (16) |
C13—C14—H14B | 109.5 | C2—C1—C5 | 103.42 (16) |
H14A—C14—H14B | 109.5 | C2—C1—H1A | 111.1 |
C13—C14—H14C | 109.5 | C5—C1—H1A | 111.1 |
H14A—C14—H14C | 109.5 | C2—C1—H1B | 111.1 |
H14B—C14—H14C | 109.5 | C5—C1—H1B | 111.1 |
C13—C15—H15A | 109.5 | H1A—C1—H1B | 109 |
| | | |
C12—C8—O9—C10 | 137.0 (2) | O9—C8—C13—C15 | 63.4 (2) |
C7—C8—O9—C10 | 20.6 (3) | C12—C8—C13—C15 | 178.4 (2) |
C13—C8—O9—C10 | −101.6 (2) | C7—C8—C13—C15 | −55.7 (2) |
C8—O9—C10—O10 | 169.22 (19) | O9—C8—C13—C16 | −176.6 (2) |
C8—O9—C10—C5 | −14.3 (3) | C12—C8—C13—C16 | −61.6 (3) |
O10—C10—C5—N6 | 174.52 (19) | C7—C8—C13—C16 | 64.4 (3) |
O9—C10—C5—N6 | −1.8 (3) | O9—C8—C13—C14 | −56.6 (2) |
O10—C10—C5—C1 | 54.1 (3) | C12—C8—C13—C14 | 58.4 (2) |
O9—C10—C5—C1 | −122.26 (19) | C7—C8—C13—C14 | −175.61 (19) |
O10—C10—C5—C4 | −59.3 (3) | N6—C7—O7—C11 | 4.3 (3) |
O9—C10—C5—C4 | 124.4 (2) | C8—C7—O7—C11 | −173.34 (17) |
C10—C5—N6—C7 | 8.8 (2) | N6—C5—C4—C3 | −73.95 (18) |
C1—C5—N6—C7 | 130.67 (17) | C10—C5—C4—C3 | 156.16 (17) |
C4—C5—N6—C7 | −119.74 (18) | C1—C5—C4—C3 | 38.61 (19) |
C5—N6—C7—O7 | −177.67 (15) | C5—C4—C3—C2 | −25.7 (2) |
C5—N6—C7—C8 | −0.5 (3) | C4—C3—C2—O2 | −177.5 (2) |
O9—C8—C7—N6 | −13.4 (3) | C4—C3—C2—C1 | 2.6 (2) |
C12—C8—C7—N6 | −126.8 (2) | O2—C2—C1—C5 | −158.34 (19) |
C13—C8—C7—N6 | 104.6 (2) | C3—C2—C1—C5 | 21.5 (2) |
O9—C8—C7—O7 | 164.06 (15) | N6—C5—C1—C2 | 77.38 (18) |
C12—C8—C7—O7 | 50.7 (2) | C10—C5—C1—C2 | −156.85 (15) |
C13—C8—C7—O7 | −77.93 (19) | C4—C5—C1—C2 | −36.53 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11C···O2i | 0.96 | 2.58 | 3.476 (3) | 155 |
C12—H12B···O2ii | 0.96 | 2.69 | 3.548 (3) | 149 |
C15—H15A···O10iii | 0.96 | 2.74 | 3.596 (3) | 149 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, y−1/2, −z+1; (iii) −x+2, y+1/2, −z+2. |
(2) (5
S,8
R)-8-
tert-Butyl-7-methoxy-8-methyl-9-oxa-6-azaspiro[4.5]decane-2,10-dione
top
Crystal data top
C14H21NO4 | F(000) = 288 |
Mr = 267.32 | Dx = 1.224 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2829 reflections |
a = 8.7007 (3) Å | θ = 3.1–28.5° |
b = 6.3466 (2) Å | µ = 0.09 mm−1 |
c = 13.3458 (4) Å | T = 293 K |
β = 100.243 (3)° | Block, colourless |
V = 725.21 (4) Å3 | 0.34 × 0.27 × 0.1 mm |
Z = 2 | |
Data collection top
Rigaku Oxford Diffraction SuperNova Dual Source diffractometer with an
Atlas detector | 3396 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 2235 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.033 |
Detector resolution: 10.3756 pixels mm-1 | θmax = 28.5°, θmin = 3.1° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −8→8 |
Tmin = 0.800, Tmax = 1 | l = −17→17 |
9804 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.052 | w = 1/[σ2(Fo2) + (0.0485P)2 + 0.0692P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.127 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.12 e Å−3 |
3396 reflections | Δρmin = −0.15 e Å−3 |
172 parameters | Absolute structure: Flack x determined using 774 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons & Flack, 2004) |
1 restraint | Absolute structure parameter: −0.5 (6) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O9 | 0.5881 (3) | 0.4090 (4) | 0.69474 (18) | 0.0612 (7) | |
O10 | 0.3340 (3) | 0.4043 (5) | 0.6699 (2) | 0.0793 (9) | |
O2 | 0.2874 (3) | −0.0121 (5) | 0.9970 (2) | 0.0829 (9) | |
O7 | 0.8769 (2) | 0.1094 (4) | 0.86184 (15) | 0.0565 (6) | |
N6 | 0.6134 (3) | 0.0889 (4) | 0.84076 (18) | 0.0447 (6) | |
C7 | 0.7325 (4) | 0.1604 (5) | 0.8123 (2) | 0.0456 (8) | |
C8 | 0.7420 (4) | 0.3133 (6) | 0.7262 (2) | 0.0503 (8) | |
C10 | 0.4541 (4) | 0.3267 (6) | 0.7122 (2) | 0.0540 (9) | |
C5 | 0.4587 (3) | 0.1519 (5) | 0.7888 (2) | 0.0449 (8) | |
C1 | 0.3674 (4) | 0.2171 (6) | 0.8721 (2) | 0.0527 (8) | |
H1A | 0.4322 | 0.2998 | 0.9244 | 0.063* | |
H1B | 0.2756 | 0.2987 | 0.8437 | 0.063* | |
C13 | 0.7855 (4) | 0.2079 (7) | 0.6300 (2) | 0.0624 (10) | |
C16 | 0.9484 (4) | 0.1132 (9) | 0.6517 (3) | 0.0869 (14) | |
H16A | 1.023 | 0.2215 | 0.6754 | 0.13* | |
H16B | 0.9723 | 0.0522 | 0.5904 | 0.13* | |
H16C | 0.9528 | 0.0061 | 0.7029 | 0.13* | |
C2 | 0.3223 (4) | 0.0127 (7) | 0.9141 (3) | 0.0556 (9) | |
C14 | 0.6703 (5) | 0.0321 (9) | 0.5926 (3) | 0.0847 (14) | |
H14A | 0.5663 | 0.0885 | 0.5784 | 0.127* | |
H14B | 0.6762 | −0.0746 | 0.6442 | 0.127* | |
H14C | 0.6957 | −0.0285 | 0.5317 | 0.127* | |
C15 | 0.7788 (6) | 0.3716 (10) | 0.5444 (3) | 0.0989 (17) | |
H15A | 0.6763 | 0.4327 | 0.5299 | 0.148* | |
H15B | 0.8014 | 0.3042 | 0.4843 | 0.148* | |
H15C | 0.8545 | 0.4801 | 0.5655 | 0.148* | |
C4 | 0.3693 (4) | −0.0481 (6) | 0.7447 (3) | 0.0585 (10) | |
H4A | 0.2758 | −0.0109 | 0.6967 | 0.07* | |
H4B | 0.4347 | −0.1367 | 0.7105 | 0.07* | |
C12 | 0.8465 (5) | 0.4980 (7) | 0.7669 (3) | 0.0764 (12) | |
H12A | 0.9512 | 0.4486 | 0.7895 | 0.115* | |
H12B | 0.8083 | 0.5616 | 0.8229 | 0.115* | |
H12C | 0.8459 | 0.6004 | 0.7138 | 0.115* | |
C3 | 0.3281 (5) | −0.1588 (6) | 0.8369 (3) | 0.0695 (11) | |
H3A | 0.2277 | −0.2286 | 0.8197 | 0.083* | |
H3B | 0.4067 | −0.2628 | 0.863 | 0.083* | |
C11 | 0.8824 (4) | −0.0170 (7) | 0.9517 (2) | 0.0601 (9) | |
H11A | 0.9892 | −0.0449 | 0.9814 | 0.09* | |
H11B | 0.829 | −0.1478 | 0.9339 | 0.09* | |
H11C | 0.8325 | 0.0571 | 0.9999 | 0.09* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O9 | 0.0588 (15) | 0.0650 (15) | 0.0630 (14) | 0.0114 (13) | 0.0191 (12) | 0.0269 (12) |
O10 | 0.0634 (17) | 0.101 (2) | 0.0735 (17) | 0.0297 (16) | 0.0121 (13) | 0.0361 (16) |
O2 | 0.097 (2) | 0.0891 (19) | 0.0738 (17) | 0.0140 (17) | 0.0450 (16) | 0.0233 (16) |
O7 | 0.0439 (12) | 0.0766 (16) | 0.0467 (12) | 0.0005 (12) | 0.0023 (10) | 0.0106 (12) |
N6 | 0.0424 (15) | 0.0513 (16) | 0.0401 (13) | 0.0000 (13) | 0.0061 (11) | 0.0029 (12) |
C7 | 0.0469 (19) | 0.051 (2) | 0.0376 (15) | 0.0015 (16) | 0.0029 (14) | 0.0012 (15) |
C8 | 0.0426 (18) | 0.064 (2) | 0.0443 (17) | −0.0006 (17) | 0.0082 (14) | 0.0079 (16) |
C10 | 0.053 (2) | 0.064 (2) | 0.0455 (18) | 0.0091 (19) | 0.0114 (16) | 0.0072 (17) |
C5 | 0.0441 (17) | 0.0508 (19) | 0.0391 (15) | 0.0016 (15) | 0.0056 (13) | 0.0031 (15) |
C1 | 0.0512 (19) | 0.062 (2) | 0.0462 (18) | 0.0065 (18) | 0.0130 (15) | 0.0041 (17) |
C13 | 0.052 (2) | 0.095 (3) | 0.0408 (17) | 0.005 (2) | 0.0110 (15) | 0.0073 (19) |
C16 | 0.059 (2) | 0.135 (4) | 0.070 (2) | 0.020 (3) | 0.0202 (19) | 0.002 (3) |
C2 | 0.0433 (18) | 0.065 (2) | 0.060 (2) | 0.0073 (17) | 0.0136 (16) | 0.0103 (19) |
C14 | 0.083 (3) | 0.112 (4) | 0.060 (2) | −0.005 (3) | 0.017 (2) | −0.032 (3) |
C15 | 0.101 (3) | 0.143 (5) | 0.059 (2) | 0.022 (3) | 0.032 (2) | 0.038 (3) |
C4 | 0.052 (2) | 0.067 (3) | 0.054 (2) | −0.0018 (18) | 0.0031 (16) | −0.0098 (18) |
C12 | 0.089 (3) | 0.073 (3) | 0.068 (2) | −0.026 (2) | 0.016 (2) | 0.007 (2) |
C3 | 0.071 (3) | 0.063 (2) | 0.075 (3) | −0.011 (2) | 0.013 (2) | −0.001 (2) |
C11 | 0.052 (2) | 0.074 (2) | 0.0495 (18) | 0.0027 (19) | −0.0024 (15) | 0.0119 (19) |
Geometric parameters (Å, º) top
O9—C10 | 1.335 (4) | C16—H16B | 0.96 |
O9—C8 | 1.462 (4) | C16—H16C | 0.96 |
O10—C10 | 1.202 (4) | C2—C3 | 1.506 (5) |
O2—C2 | 1.210 (4) | C14—H14A | 0.96 |
O7—C7 | 1.351 (3) | C14—H14B | 0.96 |
O7—C11 | 1.437 (4) | C14—H14C | 0.96 |
N6—C7 | 1.251 (4) | C15—H15A | 0.96 |
N6—C5 | 1.456 (4) | C15—H15B | 0.96 |
C7—C8 | 1.517 (4) | C15—H15C | 0.96 |
C8—C12 | 1.524 (5) | C4—C3 | 1.515 (5) |
C8—C13 | 1.553 (5) | C4—H4A | 0.97 |
C10—C5 | 1.504 (5) | C4—H4B | 0.97 |
C5—C1 | 1.534 (4) | C12—H12A | 0.96 |
C5—C4 | 1.549 (5) | C12—H12B | 0.96 |
C1—C2 | 1.493 (5) | C12—H12C | 0.96 |
C1—H1A | 0.97 | C3—H3A | 0.97 |
C1—H1B | 0.97 | C3—H3B | 0.97 |
C13—C16 | 1.519 (5) | C11—H11A | 0.96 |
C13—C14 | 1.523 (6) | C11—H11B | 0.96 |
C13—C15 | 1.538 (6) | C11—H11C | 0.96 |
C16—H16A | 0.96 | | |
| | | |
C10—O9—C8 | 124.8 (3) | O2—C2—C1 | 125.6 (4) |
C7—O7—C11 | 115.6 (2) | O2—C2—C3 | 125.2 (4) |
C7—N6—C5 | 120.1 (3) | C1—C2—C3 | 109.2 (3) |
N6—C7—O7 | 120.9 (3) | C13—C14—H14A | 109.5 |
N6—C7—C8 | 128.5 (3) | C13—C14—H14B | 109.5 |
O7—C7—C8 | 110.7 (3) | H14A—C14—H14B | 109.5 |
O9—C8—C7 | 108.2 (2) | C13—C14—H14C | 109.5 |
O9—C8—C12 | 103.9 (3) | H14A—C14—H14C | 109.5 |
C7—C8—C12 | 109.4 (3) | H14B—C14—H14C | 109.5 |
O9—C8—C13 | 106.7 (2) | C13—C15—H15A | 109.5 |
C7—C8—C13 | 113.9 (3) | C13—C15—H15B | 109.5 |
C12—C8—C13 | 114.1 (3) | H15A—C15—H15B | 109.5 |
O10—C10—O9 | 118.1 (3) | C13—C15—H15C | 109.5 |
O10—C10—C5 | 122.5 (3) | H15A—C15—H15C | 109.5 |
O9—C10—C5 | 119.3 (3) | H15B—C15—H15C | 109.5 |
N6—C5—C10 | 115.9 (3) | C3—C4—C5 | 104.3 (3) |
N6—C5—C1 | 106.4 (2) | C3—C4—H4A | 110.9 |
C10—C5—C1 | 109.8 (3) | C5—C4—H4A | 110.9 |
N6—C5—C4 | 108.4 (3) | C3—C4—H4B | 110.9 |
C10—C5—C4 | 113.3 (3) | C5—C4—H4B | 110.9 |
C1—C5—C4 | 101.9 (3) | H4A—C4—H4B | 108.9 |
C2—C1—C5 | 104.0 (3) | C8—C12—H12A | 109.5 |
C2—C1—H1A | 111 | C8—C12—H12B | 109.5 |
C5—C1—H1A | 111 | H12A—C12—H12B | 109.5 |
C2—C1—H1B | 111 | C8—C12—H12C | 109.5 |
C5—C1—H1B | 111 | H12A—C12—H12C | 109.5 |
H1A—C1—H1B | 109 | H12B—C12—H12C | 109.5 |
C16—C13—C14 | 108.1 (4) | C2—C3—C4 | 105.2 (3) |
C16—C13—C15 | 108.6 (3) | C2—C3—H3A | 110.7 |
C14—C13—C15 | 108.4 (3) | C4—C3—H3A | 110.7 |
C16—C13—C8 | 111.7 (3) | C2—C3—H3B | 110.7 |
C14—C13—C8 | 110.1 (3) | C4—C3—H3B | 110.7 |
C15—C13—C8 | 109.9 (4) | H3A—C3—H3B | 108.8 |
C13—C16—H16A | 109.5 | O7—C11—H11A | 109.5 |
C13—C16—H16B | 109.5 | O7—C11—H11B | 109.5 |
H16A—C16—H16B | 109.5 | H11A—C11—H11B | 109.5 |
C13—C16—H16C | 109.5 | O7—C11—H11C | 109.5 |
H16A—C16—H16C | 109.5 | H11A—C11—H11C | 109.5 |
H16B—C16—H16C | 109.5 | H11B—C11—H11C | 109.5 |
| | | |
C5—N6—C7—O7 | 177.7 (2) | O10—C10—C5—C4 | 59.6 (5) |
C5—N6—C7—C8 | 0.0 (5) | O9—C10—C5—C4 | −124.7 (3) |
C11—O7—C7—N6 | −4.4 (4) | N6—C5—C1—C2 | −77.4 (3) |
C11—O7—C7—C8 | 173.7 (3) | C10—C5—C1—C2 | 156.5 (3) |
C10—O9—C8—C7 | −21.1 (4) | C4—C5—C1—C2 | 36.1 (3) |
C10—O9—C8—C12 | −137.3 (3) | O9—C8—C13—C16 | 176.6 (3) |
C10—O9—C8—C13 | 101.8 (4) | C7—C8—C13—C16 | −64.0 (4) |
N6—C7—C8—O9 | 13.9 (5) | C12—C8—C13—C16 | 62.5 (4) |
O7—C7—C8—O9 | −163.9 (2) | O9—C8—C13—C14 | −63.3 (4) |
N6—C7—C8—C12 | 126.5 (4) | C7—C8—C13—C14 | 56.0 (4) |
O7—C7—C8—C12 | −51.4 (4) | C12—C8—C13—C14 | −177.5 (3) |
N6—C7—C8—C13 | −104.6 (4) | O9—C8—C13—C15 | 56.0 (4) |
O7—C7—C8—C13 | 77.6 (3) | C7—C8—C13—C15 | 175.3 (3) |
C8—O9—C10—O10 | −169.3 (3) | C12—C8—C13—C15 | −58.2 (4) |
C8—O9—C10—C5 | 14.8 (5) | C5—C1—C2—O2 | 158.6 (3) |
C7—N6—C5—C10 | −8.6 (4) | C5—C1—C2—C3 | −21.1 (3) |
C7—N6—C5—C1 | −131.0 (3) | N6—C5—C4—C3 | 73.6 (3) |
C7—N6—C5—C4 | 120.0 (3) | C10—C5—C4—C3 | −156.3 (3) |
O10—C10—C5—N6 | −174.2 (3) | C1—C5—C4—C3 | −38.4 (3) |
O9—C10—C5—N6 | 1.5 (4) | O2—C2—C3—C4 | 177.2 (3) |
O10—C10—C5—C1 | −53.6 (5) | C1—C2—C3—C4 | −3.1 (4) |
O9—C10—C5—C1 | 122.1 (3) | C5—C4—C3—C2 | 25.9 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11A···O2i | 0.96 | 2.57 | 3.468 (5) | 155 |
C14—H14C···O10ii | 0.96 | 2.69 | 3.589 (4) | 156 |
C12—H12B···O2iii | 0.96 | 2.72 | 3.549 (5) | 145 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1; (iii) −x+1, y+1/2, −z+2. |