A number of cinnamamide derivatives possess anticonvulsant activity due to the presence of a number of important pharmacophore elements in their structures. In order to study the correlations between anticonvulsant activity and molecular structure, the crystal structures of three new cinnamamide derivatives with proven anticonvulsant activity were determined by X-ray diffraction, namely (
R,
S)-(2
E)-
N-(2-hydroxybutyl)-3-phenylprop-2-enamide–water (3/1), C
13H
17NO
2·0.33H
2O, (
1), (2
E)-
N-(1-hydroxy-2-methylpropan-2-yl)-3-phenylprop-2-enamide, C
13H
17NO
2, (
2), and (
R,
S)-(2
E)-
N-(1-hydroxy-3-methyl-butan-2-yl)-3-phenylprop-2-enamide, C
14H
19NO
2, (
3). Compound (
1) crystallizes in the space group
P with three molecules in the asymmetric unit, whereas compounds (
2) and (
3) crystallize in the space group
P2
1/
c with one and two molecules, respectively, in their asymmetric units. The carbonyl group of (
2) is engaged in an intramolecular hydrogen bond with the hydroxy group. This type of interaction is observed for the first time in these kinds of derivatives. A disorder of the substituent at the N atom occurs in the crystal structures of (
2) and (
3). The crystal packing of all three structures is dominated by a network of O—H
O and N—H
O hydrogen bonds, and leads to the formation of chains and/or rings. Furthermore, the crystal structures are stabilized by numerous C—H
O contacts. We analyzed the molecular structures and intermolecular interactions in order to propose a pharmacophore model for cinnamamide derivatives.
Supporting information
CCDC references: 1844810; 1844809; 1844808
Data collection: COLLECT (Bruker, 2004) for (1), (2); CrysAlis PRO (Rigaku OD, 2015) for (3). Cell refinement: SCALEPACK (Otwinowski & Minor, 1997) for (1), (2); CrysAlis PRO (Rigaku OD, 2015) for (3). Data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997) for (1), (2); CrysAlis PRO (Rigaku OD, 2015) for (3). Program(s) used to refine structure: SHELXL (Sheldrick, 2008) and SHELXL2014 (Sheldrick, 2015) for (1), (2); SIR97 (Altomare et al., 1999) and SHELXL2014 (Sheldrick, 2015) for (3). For all structures, molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
(
R,
S)-(2
E)-
N-(2-Hydroxybutyl)-3-phenylprop-2-enamide–water (3/1) (1)
top
Crystal data top
3C13H17NO2·H2O | Z = 2 |
Mr = 675.84 | F(000) = 728 |
Triclinic, P1 | Dx = 1.214 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5101 (5) Å | Cell parameters from 6123 reflections |
b = 15.023 (1) Å | θ = 1.0–25.4° |
c = 15.821 (1) Å | µ = 0.08 mm−1 |
α = 68.242 (3)° | T = 100 K |
β = 80.424 (5)° | Needle, colourless |
γ = 89.491 (5)° | 0.7 × 0.10 × 0.05 mm |
V = 1849.3 (2) Å3 | |
Data collection top
Nonius KappaCCD diffractometer | 6667 independent reflections |
Horizonally mounted graphite crystal monochromator | 4844 reflections with I > 2σ(I) |
Detector resolution: 9 pixels mm-1 | Rint = 0.041 |
CCD scans | θmax = 25.3°, θmin = 2.6° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −10→10 |
Tmin = 0.944, Tmax = 0.996 | k = −18→17 |
11581 measured reflections | l = −18→18 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.140 | w = 1/[σ2(Fo2) + (0.0469P)2 + 1.5371P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
6667 reflections | Δρmax = 0.73 e Å−3 |
474 parameters | Δρmin = −0.31 e Å−3 |
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 | |
O2C | −0.1614 (2) | 0.15256 (14) | 0.80899 (14) | 0.0263 (4) | |
H22C | −0.160 (4) | 0.087 (2) | 0.842 (2) | 0.041 (9)* | |
O1C | 0.2916 (2) | 0.09204 (13) | 0.90936 (12) | 0.0260 (4) | |
O2A | 0.4962 (2) | −0.19381 (14) | 0.60516 (13) | 0.0254 (4) | |
H22A | 0.531 (4) | −0.137 (3) | 0.611 (2) | 0.051 (10)* | |
O1A | 0.0889 (2) | −0.04206 (13) | 0.69214 (12) | 0.0268 (4) | |
O1B | 0.6159 (2) | −0.03357 (13) | 0.62084 (12) | 0.0233 (4) | |
N1A | 0.2295 (2) | −0.06915 (16) | 0.56941 (17) | 0.0230 (5) | |
HNA | 0.277 (4) | −0.041 (2) | 0.511 (2) | 0.045 (10)* | |
N1C | 0.1631 (2) | 0.09115 (15) | 0.79599 (15) | 0.0203 (5) | |
HNC | 0.128 (3) | 0.059 (2) | 0.769 (2) | 0.026 (8)* | |
O2B | 0.9462 (2) | −0.18637 (13) | 0.84533 (14) | 0.0236 (4) | |
H22B | 0.986 (5) | −0.150 (3) | 0.793 (3) | 0.064 (13)* | |
N1B | 0.6822 (3) | −0.08545 (15) | 0.76280 (16) | 0.0219 (5) | |
HNB | 0.707 (3) | −0.069 (2) | 0.808 (2) | 0.031 (8)* | |
C4A | 0.0330 (3) | 0.24882 (18) | 0.51694 (17) | 0.0188 (5) | |
C7B | 0.4176 (3) | 0.42333 (19) | 0.62210 (19) | 0.0256 (6) | |
H7B | 0.3897 | 0.4858 | 0.6185 | 0.031* | |
C5C | 0.4917 (3) | −0.24166 (19) | 1.04246 (17) | 0.0225 (6) | |
H5C | 0.5435 | −0.1995 | 1.0628 | 0.027* | |
C4C | 0.3817 (3) | −0.20594 (18) | 0.98243 (17) | 0.0203 (5) | |
C1B | 0.6325 (3) | −0.01858 (18) | 0.69143 (17) | 0.0201 (5) | |
C7C | 0.4484 (3) | −0.4009 (2) | 1.04470 (19) | 0.0272 (6) | |
H7C | 0.4708 | −0.4669 | 1.0657 | 0.033* | |
C2B | 0.5995 (3) | 0.07453 (17) | 0.70041 (17) | 0.0193 (5) | |
H2B | 0.624 | 0.0858 | 0.7521 | 0.023* | |
C6B | 0.3720 (3) | 0.38621 (19) | 0.56096 (19) | 0.0266 (6) | |
H6B | 0.312 | 0.423 | 0.5157 | 0.032* | |
C11C | −0.0355 (3) | 0.20199 (18) | 0.82735 (18) | 0.0216 (5) | |
H11C | −0.0301 | 0.1733 | 0.8948 | 0.026* | |
C1A | 0.1576 (3) | −0.01192 (18) | 0.60963 (18) | 0.0206 (5) | |
C5B | 0.4141 (3) | 0.29562 (18) | 0.56608 (18) | 0.0228 (6) | |
H5B | 0.3856 | 0.2715 | 0.5227 | 0.027* | |
C6C | 0.5253 (3) | −0.33781 (19) | 1.07222 (18) | 0.0246 (6) | |
H6C | 0.6015 | −0.3607 | 1.1118 | 0.03* | |
C12B | 0.8454 (3) | −0.33398 (18) | 0.83752 (19) | 0.0244 (6) | |
H12A | 0.7458 | −0.3673 | 0.8372 | 0.029* | |
H12B | 0.9194 | −0.3251 | 0.7793 | 0.029* | |
C2A | 0.1597 (3) | 0.09027 (18) | 0.54877 (18) | 0.0215 (5) | |
H2A | 0.2358 | 0.115 | 0.4932 | 0.026* | |
C1C | 0.2430 (3) | 0.04774 (18) | 0.86511 (17) | 0.0208 (5) | |
C3A | 0.0550 (3) | 0.14824 (18) | 0.57146 (18) | 0.0203 (5) | |
H3A | −0.0131 | 0.1209 | 0.6298 | 0.024* | |
C4B | 0.4980 (3) | 0.23860 (18) | 0.63389 (17) | 0.0187 (5) | |
C7A | −0.0274 (3) | 0.43981 (19) | 0.41874 (19) | 0.0265 (6) | |
H7A | −0.0481 | 0.5045 | 0.3854 | 0.032* | |
C9C | 0.3049 (3) | −0.27054 (19) | 0.95527 (18) | 0.0259 (6) | |
H9C | 0.2292 | −0.2481 | 0.9153 | 0.031* | |
C8B | 0.5043 (3) | 0.36863 (19) | 0.68871 (18) | 0.0233 (6) | |
H8B | 0.5376 | 0.3946 | 0.7296 | 0.028* | |
C10C | 0.1233 (3) | 0.19128 (18) | 0.77163 (18) | 0.0215 (5) | |
H10A | 0.1176 | 0.2196 | 0.7049 | 0.026* | |
H10B | 0.2092 | 0.2275 | 0.7827 | 0.026* | |
C13B | 0.9201 (3) | −0.3966 (2) | 0.9184 (2) | 0.0332 (7) | |
H13A | 0.9427 | −0.4584 | 0.9126 | 0.05* | |
H13B | 0.8462 | −0.4074 | 0.9763 | 0.05* | |
H13C | 1.0198 | −0.3646 | 0.9186 | 0.05* | |
C6A | −0.1194 (3) | 0.38856 (19) | 0.50405 (19) | 0.0252 (6) | |
H6A | −0.2038 | 0.4181 | 0.5292 | 0.03* | |
C8A | 0.0963 (3) | 0.39569 (19) | 0.38197 (18) | 0.0238 (6) | |
H8A | 0.1602 | 0.4307 | 0.3236 | 0.029* | |
C5A | −0.0889 (3) | 0.29479 (18) | 0.55254 (18) | 0.0205 (5) | |
H5A | −0.152 | 0.2607 | 0.6114 | 0.025* | |
C3C | 0.3499 (3) | −0.10396 (18) | 0.95234 (18) | 0.0221 (6) | |
H3C | 0.3915 | −0.0688 | 0.9835 | 0.027* | |
C11A | 0.3401 (3) | −0.2224 (2) | 0.6620 (2) | 0.0305 (6) | |
H11A | 0.3349 | −0.2063 | 0.7183 | 0.037* | |
C2C | 0.2690 (3) | −0.05498 (18) | 0.88593 (17) | 0.0216 (5) | |
H2C | 0.2276 | −0.0866 | 0.8516 | 0.026* | |
C11B | 0.8072 (3) | −0.23602 (19) | 0.84034 (19) | 0.0240 (6) | |
H11B | 0.7281 | −0.2466 | 0.898 | 0.029* | |
C9B | 0.5423 (3) | 0.27651 (19) | 0.69580 (18) | 0.0217 (5) | |
H9B | 0.5986 | 0.2389 | 0.7428 | 0.026* | |
C9A | 0.1262 (3) | 0.30111 (18) | 0.43027 (17) | 0.0215 (5) | |
H9A | 0.2099 | 0.2715 | 0.4047 | 0.026* | |
C12C | −0.0757 (3) | 0.30639 (19) | 0.80178 (19) | 0.0258 (6) | |
H12C | −0.1859 | 0.3091 | 0.8325 | 0.031* | |
H12D | −0.0726 | 0.3358 | 0.7342 | 0.031* | |
C3B | 0.5356 (3) | 0.14285 (18) | 0.63633 (17) | 0.0197 (5) | |
H3B | 0.5117 | 0.1274 | 0.5866 | 0.024* | |
C8C | 0.3382 (3) | −0.3664 (2) | 0.9859 (2) | 0.0298 (6) | |
H8C | 0.2853 | −0.4091 | 0.9666 | 0.036* | |
C10A | 0.2129 (3) | −0.17318 (19) | 0.6092 (2) | 0.0315 (7) | |
H10C | 0.2108 | −0.1968 | 0.5587 | 0.038* | |
H10D | 0.1085 | −0.1926 | 0.6512 | 0.038* | |
C10B | 0.7300 (3) | −0.17765 (19) | 0.75939 (19) | 0.0258 (6) | |
H10E | 0.8059 | −0.1664 | 0.7013 | 0.031* | |
H10F | 0.6349 | −0.2147 | 0.7587 | 0.031* | |
C13C | 0.0376 (3) | 0.3654 (2) | 0.8289 (2) | 0.0339 (7) | |
H13D | 0.0057 | 0.4318 | 0.8103 | 0.051* | |
H13E | 0.1468 | 0.3642 | 0.7978 | 0.051* | |
H13F | 0.0329 | 0.338 | 0.896 | 0.051* | |
C12A | 0.3156 (3) | −0.3311 (2) | 0.6904 (2) | 0.0376 (7) | |
H12E | 0.2064 | −0.352 | 0.7262 | 0.045* | |
H12F | 0.324 | −0.3462 | 0.634 | 0.045* | |
C13A | 0.4338 (4) | −0.3872 (2) | 0.7475 (2) | 0.0431 (8) | |
H13G | 0.4124 | −0.456 | 0.763 | 0.065* | |
H13H | 0.4238 | −0.3745 | 0.8046 | 0.065* | |
H13I | 0.5422 | −0.3678 | 0.7123 | 0.065* | |
O | 0.1956 (2) | 0.04507 (14) | 1.09266 (14) | 0.0266 (4) | |
HW1 | 0.221 (4) | 0.060 (3) | 1.029 (3) | 0.063 (12)* | |
HW2 | 0.132 (4) | 0.086 (3) | 1.099 (2) | 0.049 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2C | 0.0222 (9) | 0.0197 (10) | 0.0358 (11) | −0.0023 (7) | −0.0085 (8) | −0.0074 (9) |
O1C | 0.0336 (10) | 0.0229 (10) | 0.0237 (10) | −0.0038 (8) | −0.0063 (8) | −0.0106 (8) |
O2A | 0.0218 (9) | 0.0243 (10) | 0.0332 (11) | −0.0012 (7) | −0.0041 (8) | −0.0144 (9) |
O1A | 0.0312 (10) | 0.0224 (10) | 0.0226 (10) | −0.0008 (8) | 0.0011 (8) | −0.0062 (8) |
O1B | 0.0283 (9) | 0.0226 (10) | 0.0228 (10) | 0.0024 (7) | −0.0075 (8) | −0.0116 (8) |
N1A | 0.0215 (11) | 0.0193 (12) | 0.0282 (13) | 0.0027 (9) | −0.0023 (10) | −0.0099 (10) |
N1C | 0.0217 (11) | 0.0198 (12) | 0.0218 (12) | −0.0003 (9) | −0.0040 (9) | −0.0103 (10) |
O2B | 0.0262 (10) | 0.0193 (10) | 0.0237 (11) | −0.0039 (8) | −0.0058 (8) | −0.0056 (9) |
N1B | 0.0262 (11) | 0.0181 (12) | 0.0248 (12) | 0.0047 (9) | −0.0086 (9) | −0.0101 (10) |
C4A | 0.0178 (12) | 0.0185 (13) | 0.0223 (13) | 0.0000 (9) | −0.0065 (10) | −0.0090 (11) |
C7B | 0.0267 (13) | 0.0179 (14) | 0.0305 (15) | 0.0043 (10) | −0.0001 (11) | −0.0094 (12) |
C5C | 0.0205 (12) | 0.0263 (15) | 0.0202 (13) | −0.0023 (10) | −0.0027 (10) | −0.0083 (11) |
C4C | 0.0190 (12) | 0.0215 (14) | 0.0183 (13) | −0.0013 (10) | 0.0000 (10) | −0.0065 (11) |
C1B | 0.0163 (12) | 0.0203 (14) | 0.0220 (14) | −0.0016 (10) | −0.0009 (10) | −0.0072 (11) |
C7C | 0.0320 (14) | 0.0223 (15) | 0.0241 (15) | 0.0037 (11) | −0.0022 (11) | −0.0062 (12) |
C2B | 0.0209 (12) | 0.0195 (13) | 0.0183 (13) | 0.0003 (10) | −0.0024 (10) | −0.0083 (11) |
C6B | 0.0242 (13) | 0.0228 (14) | 0.0291 (15) | 0.0061 (11) | −0.0075 (11) | −0.0043 (12) |
C11C | 0.0196 (12) | 0.0227 (14) | 0.0223 (14) | −0.0015 (10) | −0.0017 (10) | −0.0087 (11) |
C1A | 0.0180 (12) | 0.0216 (14) | 0.0237 (14) | 0.0011 (10) | −0.0051 (10) | −0.0094 (11) |
C5B | 0.0204 (13) | 0.0215 (14) | 0.0255 (14) | 0.0012 (10) | −0.0049 (11) | −0.0072 (12) |
C6C | 0.0221 (13) | 0.0299 (15) | 0.0191 (14) | 0.0021 (11) | −0.0027 (10) | −0.0065 (12) |
C12B | 0.0266 (13) | 0.0196 (14) | 0.0286 (15) | 0.0014 (11) | −0.0083 (11) | −0.0094 (12) |
C2A | 0.0219 (12) | 0.0212 (14) | 0.0198 (13) | −0.0001 (10) | −0.0011 (10) | −0.0070 (11) |
C1C | 0.0187 (12) | 0.0228 (14) | 0.0206 (13) | −0.0024 (10) | 0.0010 (10) | −0.0095 (11) |
C3A | 0.0186 (12) | 0.0227 (14) | 0.0196 (13) | −0.0012 (10) | −0.0026 (10) | −0.0080 (11) |
C4B | 0.0158 (11) | 0.0179 (13) | 0.0212 (13) | 0.0003 (9) | −0.0007 (10) | −0.0068 (11) |
C7A | 0.0285 (14) | 0.0199 (14) | 0.0308 (15) | 0.0051 (11) | −0.0108 (12) | −0.0068 (12) |
C9C | 0.0285 (14) | 0.0266 (15) | 0.0235 (14) | −0.0011 (11) | −0.0094 (11) | −0.0084 (12) |
C8B | 0.0244 (13) | 0.0231 (14) | 0.0237 (14) | 0.0004 (10) | −0.0004 (11) | −0.0117 (12) |
C10C | 0.0223 (13) | 0.0174 (13) | 0.0229 (14) | 0.0000 (10) | −0.0014 (10) | −0.0064 (11) |
C13B | 0.0397 (16) | 0.0221 (15) | 0.0377 (17) | 0.0031 (12) | −0.0137 (13) | −0.0080 (13) |
C6A | 0.0216 (13) | 0.0235 (14) | 0.0299 (15) | 0.0049 (10) | −0.0032 (11) | −0.0099 (12) |
C8A | 0.0253 (13) | 0.0233 (14) | 0.0207 (14) | −0.0016 (10) | −0.0033 (11) | −0.0060 (11) |
C5A | 0.0178 (12) | 0.0228 (14) | 0.0227 (14) | 0.0003 (10) | −0.0026 (10) | −0.0110 (11) |
C3C | 0.0216 (12) | 0.0207 (14) | 0.0241 (14) | −0.0046 (10) | −0.0003 (10) | −0.0098 (11) |
C11A | 0.0278 (14) | 0.0287 (16) | 0.0344 (17) | −0.0007 (12) | −0.0052 (12) | −0.0112 (13) |
C2C | 0.0226 (13) | 0.0222 (14) | 0.0209 (14) | −0.0022 (10) | −0.0018 (10) | −0.0099 (11) |
C11B | 0.0218 (13) | 0.0218 (14) | 0.0282 (15) | −0.0006 (10) | −0.0066 (11) | −0.0081 (12) |
C9B | 0.0182 (12) | 0.0253 (14) | 0.0209 (13) | 0.0020 (10) | −0.0016 (10) | −0.0087 (11) |
C9A | 0.0220 (12) | 0.0236 (14) | 0.0210 (14) | 0.0025 (10) | −0.0044 (10) | −0.0106 (11) |
C12C | 0.0262 (13) | 0.0243 (15) | 0.0268 (15) | 0.0008 (11) | −0.0028 (11) | −0.0102 (12) |
C3B | 0.0191 (12) | 0.0212 (14) | 0.0195 (13) | −0.0001 (10) | −0.0022 (10) | −0.0091 (11) |
C8C | 0.0354 (15) | 0.0236 (15) | 0.0330 (16) | 0.0000 (12) | −0.0092 (12) | −0.0123 (13) |
C10A | 0.0272 (14) | 0.0187 (14) | 0.0462 (18) | 0.0022 (11) | −0.0008 (13) | −0.0117 (13) |
C10B | 0.0307 (14) | 0.0204 (14) | 0.0309 (15) | 0.0049 (11) | −0.0096 (12) | −0.0133 (12) |
C13C | 0.0338 (15) | 0.0301 (16) | 0.0431 (18) | −0.0001 (12) | −0.0033 (13) | −0.0211 (14) |
C12A | 0.0260 (14) | 0.0227 (16) | 0.060 (2) | 0.0008 (12) | −0.0085 (14) | −0.0105 (15) |
C13A | 0.057 (2) | 0.0313 (18) | 0.0391 (19) | 0.0004 (15) | −0.0111 (16) | −0.0100 (15) |
O | 0.0356 (11) | 0.0228 (11) | 0.0224 (11) | 0.0003 (9) | −0.0046 (8) | −0.0096 (9) |
Geometric parameters (Å, º) top
O2C—C11C | 1.435 (3) | C3A—H3A | 0.95 |
O2C—H22C | 0.92 (3) | C4B—C9B | 1.402 (3) |
O1C—C1C | 1.245 (3) | C4B—C3B | 1.459 (3) |
O2A—C11A | 1.444 (3) | C7A—C6A | 1.384 (4) |
O2A—H22A | 0.94 (4) | C7A—C8A | 1.398 (4) |
O1A—C1A | 1.250 (3) | C7A—H7A | 0.95 |
O1B—C1B | 1.248 (3) | C9C—C8C | 1.381 (4) |
N1A—C1A | 1.336 (3) | C9C—H9C | 0.95 |
N1A—C10A | 1.450 (3) | C8B—C9B | 1.386 (4) |
N1A—HNA | 0.89 (3) | C8B—H8B | 0.95 |
N1C—C1C | 1.339 (3) | C10C—H10A | 0.99 |
N1C—C10C | 1.460 (3) | C10C—H10B | 0.99 |
N1C—HNC | 0.84 (3) | C13B—H13A | 0.98 |
O2B—C11B | 1.432 (3) | C13B—H13B | 0.98 |
O2B—H22B | 0.81 (4) | C13B—H13C | 0.98 |
N1B—C1B | 1.332 (3) | C6A—C5A | 1.378 (4) |
N1B—C10B | 1.458 (3) | C6A—H6A | 0.95 |
N1B—HNB | 0.88 (3) | C8A—C9A | 1.386 (4) |
C4A—C5A | 1.397 (3) | C8A—H8A | 0.95 |
C4A—C9A | 1.406 (4) | C5A—H5A | 0.95 |
C4A—C3A | 1.464 (4) | C3C—C2C | 1.333 (4) |
C7B—C6B | 1.388 (4) | C3C—H3C | 0.95 |
C7B—C8B | 1.391 (4) | C11A—C10A | 1.498 (4) |
C7B—H7B | 0.95 | C11A—C12A | 1.532 (4) |
C5C—C6C | 1.387 (4) | C11A—H11A | 1 |
C5C—C4C | 1.406 (4) | C2C—H2C | 0.95 |
C5C—H5C | 0.95 | C11B—C10B | 1.509 (4) |
C4C—C9C | 1.402 (3) | C11B—H11B | 1 |
C4C—C3C | 1.463 (4) | C9B—H9B | 0.95 |
C1B—C2B | 1.477 (3) | C9A—H9A | 0.95 |
C7C—C6C | 1.388 (4) | C12C—C13C | 1.527 (4) |
C7C—C8C | 1.393 (4) | C12C—H12C | 0.99 |
C7C—H7C | 0.95 | C12C—H12D | 0.99 |
C2B—C3B | 1.334 (4) | C3B—H3B | 0.95 |
C2B—H2B | 0.95 | C8C—H8C | 0.95 |
C6B—C5B | 1.381 (4) | C10A—H10C | 0.99 |
C6B—H6B | 0.95 | C10A—H10D | 0.99 |
C11C—C12C | 1.519 (4) | C10B—H10E | 0.99 |
C11C—C10C | 1.528 (3) | C10B—H10F | 0.99 |
C11C—H11C | 1 | C13C—H13D | 0.98 |
C1A—C2A | 1.477 (4) | C13C—H13E | 0.98 |
C5B—C4B | 1.399 (4) | C13C—H13F | 0.98 |
C5B—H5B | 0.95 | C12A—C13A | 1.504 (4) |
C6C—H6C | 0.95 | C12A—H12E | 0.99 |
C12B—C13B | 1.515 (4) | C12A—H12F | 0.99 |
C12B—C11B | 1.519 (3) | C13A—H13G | 0.98 |
C12B—H12A | 0.99 | C13A—H13H | 0.98 |
C12B—H12B | 0.99 | C13A—H13I | 0.98 |
C2A—C3A | 1.339 (3) | O—HW1 | 0.93 (4) |
C2A—H2A | 0.95 | O—HW2 | 0.84 (4) |
C1C—C2C | 1.477 (4) | | |
| | | |
C11C—O2C—H22C | 109 (2) | H10A—C10C—H10B | 107.9 |
C11A—O2A—H22A | 107 (2) | C12B—C13B—H13A | 109.5 |
C1A—N1A—C10A | 124.5 (2) | C12B—C13B—H13B | 109.5 |
C1A—N1A—HNA | 116 (2) | H13A—C13B—H13B | 109.5 |
C10A—N1A—HNA | 119 (2) | C12B—C13B—H13C | 109.5 |
C1C—N1C—C10C | 121.6 (2) | H13A—C13B—H13C | 109.5 |
C1C—N1C—HNC | 119 (2) | H13B—C13B—H13C | 109.5 |
C10C—N1C—HNC | 119 (2) | C5A—C6A—C7A | 120.2 (2) |
C11B—O2B—H22B | 109 (3) | C5A—C6A—H6A | 119.9 |
C1B—N1B—C10B | 121.2 (2) | C7A—C6A—H6A | 119.9 |
C1B—N1B—HNB | 119.0 (19) | C9A—C8A—C7A | 120.3 (2) |
C10B—N1B—HNB | 118.4 (19) | C9A—C8A—H8A | 119.9 |
C5A—C4A—C9A | 118.3 (2) | C7A—C8A—H8A | 119.9 |
C5A—C4A—C3A | 118.1 (2) | C6A—C5A—C4A | 121.3 (2) |
C9A—C4A—C3A | 123.6 (2) | C6A—C5A—H5A | 119.3 |
C6B—C7B—C8B | 119.7 (2) | C4A—C5A—H5A | 119.3 |
C6B—C7B—H7B | 120.1 | C2C—C3C—C4C | 127.1 (2) |
C8B—C7B—H7B | 120.1 | C2C—C3C—H3C | 116.4 |
C6C—C5C—C4C | 120.6 (2) | C4C—C3C—H3C | 116.4 |
C6C—C5C—H5C | 119.7 | O2A—C11A—C10A | 110.8 (2) |
C4C—C5C—H5C | 119.7 | O2A—C11A—C12A | 107.3 (2) |
C9C—C4C—C5C | 118.1 (2) | C10A—C11A—C12A | 109.5 (2) |
C9C—C4C—C3C | 122.9 (2) | O2A—C11A—H11A | 109.7 |
C5C—C4C—C3C | 119.0 (2) | C10A—C11A—H11A | 109.7 |
O1B—C1B—N1B | 121.9 (2) | C12A—C11A—H11A | 109.7 |
O1B—C1B—C2B | 122.0 (2) | C3C—C2C—C1C | 120.8 (2) |
N1B—C1B—C2B | 116.1 (2) | C3C—C2C—H2C | 119.6 |
C6C—C7C—C8C | 119.2 (3) | C1C—C2C—H2C | 119.6 |
C6C—C7C—H7C | 120.4 | O2B—C11B—C10B | 111.9 (2) |
C8C—C7C—H7C | 120.4 | O2B—C11B—C12B | 111.3 (2) |
C3B—C2B—C1B | 120.4 (2) | C10B—C11B—C12B | 110.8 (2) |
C3B—C2B—H2B | 119.8 | O2B—C11B—H11B | 107.5 |
C1B—C2B—H2B | 119.8 | C10B—C11B—H11B | 107.5 |
C5B—C6B—C7B | 119.8 (3) | C12B—C11B—H11B | 107.5 |
C5B—C6B—H6B | 120.1 | C8B—C9B—C4B | 120.2 (2) |
C7B—C6B—H6B | 120.1 | C8B—C9B—H9B | 119.9 |
O2C—C11C—C12C | 107.7 (2) | C4B—C9B—H9B | 119.9 |
O2C—C11C—C10C | 109.4 (2) | C8A—C9A—C4A | 120.3 (2) |
C12C—C11C—C10C | 112.0 (2) | C8A—C9A—H9A | 119.8 |
O2C—C11C—H11C | 109.3 | C4A—C9A—H9A | 119.8 |
C12C—C11C—H11C | 109.3 | C11C—C12C—C13C | 113.5 (2) |
C10C—C11C—H11C | 109.3 | C11C—C12C—H12C | 108.9 |
O1A—C1A—N1A | 123.1 (2) | C13C—C12C—H12C | 108.9 |
O1A—C1A—C2A | 121.6 (2) | C11C—C12C—H12D | 108.9 |
N1A—C1A—C2A | 115.3 (2) | C13C—C12C—H12D | 108.9 |
C6B—C5B—C4B | 121.3 (2) | H12C—C12C—H12D | 107.7 |
C6B—C5B—H5B | 119.3 | C2B—C3B—C4B | 127.4 (2) |
C4B—C5B—H5B | 119.3 | C2B—C3B—H3B | 116.3 |
C5C—C6C—C7C | 120.6 (2) | C4B—C3B—H3B | 116.3 |
C5C—C6C—H6C | 119.7 | C9C—C8C—C7C | 120.6 (3) |
C7C—C6C—H6C | 119.7 | C9C—C8C—H8C | 119.7 |
C13B—C12B—C11B | 113.2 (2) | C7C—C8C—H8C | 119.7 |
C13B—C12B—H12A | 108.9 | N1A—C10A—C11A | 116.0 (2) |
C11B—C12B—H12A | 108.9 | N1A—C10A—H10C | 108.3 |
C13B—C12B—H12B | 108.9 | C11A—C10A—H10C | 108.3 |
C11B—C12B—H12B | 108.9 | N1A—C10A—H10D | 108.3 |
H12A—C12B—H12B | 107.8 | C11A—C10A—H10D | 108.3 |
C3A—C2A—C1A | 120.4 (2) | H10C—C10A—H10D | 107.4 |
C3A—C2A—H2A | 119.8 | N1B—C10B—C11B | 112.5 (2) |
C1A—C2A—H2A | 119.8 | N1B—C10B—H10E | 109.1 |
O1C—C1C—N1C | 121.4 (2) | C11B—C10B—H10E | 109.1 |
O1C—C1C—C2C | 122.2 (2) | N1B—C10B—H10F | 109.1 |
N1C—C1C—C2C | 116.4 (2) | C11B—C10B—H10F | 109.1 |
C2A—C3A—C4A | 127.7 (2) | H10E—C10B—H10F | 107.8 |
C2A—C3A—H3A | 116.2 | C12C—C13C—H13D | 109.5 |
C4A—C3A—H3A | 116.2 | C12C—C13C—H13E | 109.5 |
C5B—C4B—C9B | 118.4 (2) | H13D—C13C—H13E | 109.5 |
C5B—C4B—C3B | 118.3 (2) | C12C—C13C—H13F | 109.5 |
C9B—C4B—C3B | 123.3 (2) | H13D—C13C—H13F | 109.5 |
C6A—C7A—C8A | 119.6 (2) | H13E—C13C—H13F | 109.5 |
C6A—C7A—H7A | 120.2 | C13A—C12A—C11A | 113.5 (2) |
C8A—C7A—H7A | 120.2 | C13A—C12A—H12E | 108.9 |
C8C—C9C—C4C | 120.8 (2) | C11A—C12A—H12E | 108.9 |
C8C—C9C—H9C | 119.6 | C13A—C12A—H12F | 108.9 |
C4C—C9C—H9C | 119.6 | C11A—C12A—H12F | 108.9 |
C9B—C8B—C7B | 120.5 (2) | H12E—C12A—H12F | 107.7 |
C9B—C8B—H8B | 119.8 | C12A—C13A—H13G | 109.5 |
C7B—C8B—H8B | 119.8 | C12A—C13A—H13H | 109.5 |
N1C—C10C—C11C | 112.3 (2) | H13G—C13A—H13H | 109.5 |
N1C—C10C—H10A | 109.1 | C12A—C13A—H13I | 109.5 |
C11C—C10C—H10A | 109.1 | H13G—C13A—H13I | 109.5 |
N1C—C10C—H10B | 109.1 | H13H—C13A—H13I | 109.5 |
C11C—C10C—H10B | 109.1 | HW1—O—HW2 | 105 (3) |
| | | |
C6C—C5C—C4C—C9C | 1.3 (4) | C9A—C4A—C5A—C6A | 0.8 (3) |
C6C—C5C—C4C—C3C | −179.8 (2) | C3A—C4A—C5A—C6A | −178.3 (2) |
C10B—N1B—C1B—O1B | 4.2 (4) | C9C—C4C—C3C—C2C | −11.9 (4) |
C10B—N1B—C1B—C2B | −175.3 (2) | C5C—C4C—C3C—C2C | 169.3 (2) |
O1B—C1B—C2B—C3B | 6.6 (4) | C4C—C3C—C2C—C1C | 178.3 (2) |
N1B—C1B—C2B—C3B | −173.9 (2) | O1C—C1C—C2C—C3C | −1.6 (4) |
C8B—C7B—C6B—C5B | −0.6 (4) | N1C—C1C—C2C—C3C | 178.7 (2) |
C10A—N1A—C1A—O1A | 11.8 (4) | C13B—C12B—C11B—O2B | 55.9 (3) |
C10A—N1A—C1A—C2A | −166.2 (2) | C13B—C12B—C11B—C10B | −178.8 (2) |
C7B—C6B—C5B—C4B | 2.1 (4) | C7B—C8B—C9B—C4B | 2.0 (4) |
C4C—C5C—C6C—C7C | −1.3 (4) | C5B—C4B—C9B—C8B | −0.5 (3) |
C8C—C7C—C6C—C5C | 0.7 (4) | C3B—C4B—C9B—C8B | 179.2 (2) |
O1A—C1A—C2A—C3A | −17.8 (4) | C7A—C8A—C9A—C4A | −0.4 (4) |
N1A—C1A—C2A—C3A | 160.2 (2) | C5A—C4A—C9A—C8A | −0.2 (3) |
C10C—N1C—C1C—O1C | −2.6 (4) | C3A—C4A—C9A—C8A | 178.8 (2) |
C10C—N1C—C1C—C2C | 177.1 (2) | O2C—C11C—C12C—C13C | 172.8 (2) |
C1A—C2A—C3A—C4A | −175.6 (2) | C10C—C11C—C12C—C13C | −66.9 (3) |
C5A—C4A—C3A—C2A | 177.3 (2) | C1B—C2B—C3B—C4B | −178.9 (2) |
C9A—C4A—C3A—C2A | −1.7 (4) | C5B—C4B—C3B—C2B | −172.7 (2) |
C6B—C5B—C4B—C9B | −1.5 (4) | C9B—C4B—C3B—C2B | 7.6 (4) |
C6B—C5B—C4B—C3B | 178.7 (2) | C4C—C9C—C8C—C7C | 0.2 (4) |
C5C—C4C—C9C—C8C | −0.8 (4) | C6C—C7C—C8C—C9C | −0.1 (4) |
C3C—C4C—C9C—C8C | −179.6 (2) | C1A—N1A—C10A—C11A | −95.3 (3) |
C6B—C7B—C8B—C9B | −1.5 (4) | O2A—C11A—C10A—N1A | −55.9 (3) |
C1C—N1C—C10C—C11C | −87.8 (3) | C12A—C11A—C10A—N1A | −174.0 (2) |
O2C—C11C—C10C—N1C | −60.9 (3) | C1B—N1B—C10B—C11B | 170.6 (2) |
C12C—C11C—C10C—N1C | 179.8 (2) | O2B—C11B—C10B—N1B | −58.8 (3) |
C8A—C7A—C6A—C5A | 0.2 (4) | C12B—C11B—C10B—N1B | 176.3 (2) |
C6A—C7A—C8A—C9A | 0.4 (4) | O2A—C11A—C12A—C13A | 62.2 (3) |
C7A—C6A—C5A—C4A | −0.9 (4) | C10A—C11A—C12A—C13A | −177.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2B—H2B···O2Ci | 0.95 | 2.53 | 3.341 (3) | 144 |
C2A—H2A···O2Aii | 0.95 | 2.55 | 3.438 (3) | 155 |
O—HW1···O1C | 0.93 (4) | 1.77 (4) | 2.698 (3) | 174 (3) |
O—HW2···O2Biii | 0.84 (4) | 2.07 (4) | 2.833 (3) | 152 (3) |
N1B—HNB···Oiii | 0.88 (3) | 2.05 (3) | 2.917 (3) | 169 (3) |
N1C—HNC···O1A | 0.84 (3) | 2.33 (3) | 3.148 (3) | 167 (3) |
N1A—HNA···O1Bii | 0.89 (3) | 2.02 (4) | 2.906 (3) | 176 (3) |
O2B—H22B···O1Ai | 0.81 (4) | 1.90 (4) | 2.687 (3) | 163 (4) |
O2C—H22C···Oiv | 0.92 (3) | 1.87 (3) | 2.786 (3) | 170 (3) |
O2A—H22A···O1B | 0.94 (4) | 1.79 (4) | 2.732 (2) | 175 (3) |
C9A—H9A···O2Aii | 0.95 | 2.76 | 3.635 (3) | 155 |
C9B—H9B···O2Ci | 0.95 | 2.57 | 3.461 (3) | 156 |
C10B—H10F···O2A | 0.99 | 2.79 | 3.469 (3) | 126 |
C5B—H5B···O2Aii | 0.95 | 2.74 | 3.553 (3) | 144 |
C2C—H2C···O1A | 0.95 | 2.82 | 3.592 (3) | 140 |
C5C—H5C···O1Ciii | 0.95 | 2.35 | 3.294 (3) | 170 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1; (iii) −x+1, −y, −z+2; (iv) −x, −y, −z+2. |
(2
E)-
N-(1-Hydroxy-2-methylpropan-2-yl)-3-phenylprop-2-enamide (2)
top
Crystal data top
C13H17NO2 | F(000) = 472 |
Mr = 219.27 | Dx = 1.209 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5360 reflections |
a = 5.9920 (1) Å | θ = 1.0–27.5° |
b = 14.4510 (4) Å | µ = 0.08 mm−1 |
c = 14.3460 (3) Å | T = 100 K |
β = 104.178 (2)° | Prism, colourless |
V = 1204.39 (5) Å3 | 0.8 × 0.23 × 0.18 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD diffractometer | 2753 independent reflections |
Horizonally mounted graphite crystal monochromator | 2207 reflections with I > 2σ(I) |
Detector resolution: 9 pixels mm-1 | Rint = 0.033 |
CCD scans | θmax = 27.5°, θmin = 2.8° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −7→7 |
Tmin = 0.938, Tmax = 0.986 | k = −18→18 |
9597 measured reflections | l = −18→18 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0561P)2 + 0.4623P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.121 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.30 e Å−3 |
2753 reflections | Δρmin = −0.28 e Å−3 |
171 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.057 (5) |
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 | Occ. (<1) |
C9 | −0.0940 (2) | −0.01844 (9) | 0.34394 (9) | 0.0223 (3) | |
H9 | −0.1054 | 0.0109 | 0.4003 | 0.027* | |
C8 | −0.2620 (2) | −0.08122 (9) | 0.29948 (10) | 0.0249 (3) | |
H8 | −0.3844 | −0.0943 | 0.3267 | 0.03* | |
C7 | −0.2485 (2) | −0.12465 (9) | 0.21469 (10) | 0.0278 (3) | |
H7 | −0.3614 | −0.1668 | 0.1854 | 0.033* | |
C6 | −0.0676 (2) | −0.10540 (10) | 0.17371 (10) | 0.0282 (3) | |
H6 | −0.0598 | −0.1337 | 0.1164 | 0.034* | |
C5 | 0.1028 (2) | −0.04350 (9) | 0.21858 (9) | 0.0240 (3) | |
H5 | 0.2255 | −0.0314 | 0.1913 | 0.029* | |
C4 | 0.0924 (2) | 0.00087 (9) | 0.30435 (9) | 0.0200 (3) | |
C3 | 0.2791 (2) | 0.06461 (9) | 0.34958 (9) | 0.0212 (3) | |
H3 | 0.4062 | 0.0661 | 0.3232 | 0.025* | |
C2 | 0.2859 (2) | 0.12042 (9) | 0.42416 (9) | 0.0221 (3) | |
H2 | 0.1609 | 0.1228 | 0.4518 | 0.026* | |
C1 | 0.4915 (2) | 0.17893 (9) | 0.46361 (9) | 0.0204 (3) | |
O1 | 0.66593 (17) | 0.17293 (8) | 0.43161 (8) | 0.0336 (3) | |
N1 | 0.47124 (19) | 0.23621 (8) | 0.53389 (8) | 0.0246 (3) | |
H1 | 0.328 (4) | 0.2400 (13) | 0.5460 (13) | 0.041 (5)* | |
C10 | 0.6397 (2) | 0.30564 (9) | 0.58558 (10) | 0.0245 (3) | |
C13 | 0.5663 (4) | 0.3288 (2) | 0.67665 (19) | 0.0768 (11) | 0.894 (3) |
H13A | 0.4052 | 0.3435 | 0.6609 | 0.115* | 0.894 (3) |
H13B | 0.6528 | 0.3811 | 0.7074 | 0.115* | 0.894 (3) |
H13C | 0.5946 | 0.2767 | 0.7193 | 0.115* | 0.894 (3) |
C12 | 0.6320 (4) | 0.38950 (13) | 0.52158 (19) | 0.0654 (9) | 0.894 (3) |
H12A | 0.6701 | 0.3713 | 0.463 | 0.098* | 0.894 (3) |
H12B | 0.741 | 0.4347 | 0.5541 | 0.098* | 0.894 (3) |
H12C | 0.4802 | 0.4157 | 0.507 | 0.098* | 0.894 (3) |
C11 | 0.8847 (2) | 0.26724 (10) | 0.61600 (10) | 0.0226 (3) | 0.894 (3) |
H11A | 0.9731 | 0.3044 | 0.6685 | 0.027* | 0.894 (3) |
H11B | 0.8789 | 0.2046 | 0.6396 | 0.027* | 0.894 (3) |
C13A | 0.759 (2) | 0.2557 (9) | 0.6757 (9) | 0.025 (3)* | 0.106 (3) |
H13D | 0.647 | 0.234 | 0.7082 | 0.037* | 0.106 (3) |
H13E | 0.8638 | 0.2972 | 0.717 | 0.037* | 0.106 (3) |
H13F | 0.843 | 0.204 | 0.6595 | 0.037* | 0.106 (3) |
C12A | 0.483 (2) | 0.3928 (10) | 0.6071 (10) | 0.030 (3)* | 0.106 (3) |
H12D | 0.4078 | 0.422 | 0.5475 | 0.045* | 0.106 (3) |
H12E | 0.5798 | 0.4369 | 0.648 | 0.045* | 0.106 (3) |
H12F | 0.3687 | 0.3704 | 0.6383 | 0.045* | 0.106 (3) |
C11A | 0.803 (2) | 0.3483 (9) | 0.5319 (9) | 0.025 (3)* | 0.106 (3) |
H11C | 0.8699 | 0.4052 | 0.5624 | 0.029* | 0.106 (3) |
H11D | 0.7253 | 0.361 | 0.4654 | 0.029* | 0.106 (3) |
O2 | 0.99998 (19) | 0.26643 (9) | 0.53983 (9) | 0.0457 (4) | |
H2O | 0.901 (4) | 0.2350 (16) | 0.4926 (17) | 0.062 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C9 | 0.0222 (6) | 0.0194 (6) | 0.0246 (6) | 0.0013 (5) | 0.0041 (5) | −0.0009 (5) |
C8 | 0.0197 (6) | 0.0206 (6) | 0.0324 (7) | −0.0003 (5) | 0.0027 (5) | 0.0033 (5) |
C7 | 0.0258 (7) | 0.0212 (6) | 0.0302 (7) | −0.0010 (5) | −0.0049 (5) | −0.0011 (5) |
C6 | 0.0301 (7) | 0.0272 (7) | 0.0229 (6) | 0.0018 (6) | −0.0018 (5) | −0.0052 (5) |
C5 | 0.0231 (6) | 0.0252 (7) | 0.0221 (6) | 0.0016 (5) | 0.0025 (5) | −0.0021 (5) |
C4 | 0.0192 (6) | 0.0171 (6) | 0.0218 (6) | 0.0021 (5) | 0.0014 (5) | 0.0003 (5) |
C3 | 0.0191 (6) | 0.0213 (6) | 0.0233 (6) | −0.0008 (5) | 0.0057 (5) | −0.0012 (5) |
C2 | 0.0189 (6) | 0.0223 (6) | 0.0260 (6) | −0.0025 (5) | 0.0075 (5) | −0.0037 (5) |
C1 | 0.0190 (6) | 0.0200 (6) | 0.0229 (6) | −0.0010 (5) | 0.0067 (5) | −0.0021 (5) |
O1 | 0.0221 (5) | 0.0429 (6) | 0.0399 (6) | −0.0084 (4) | 0.0155 (4) | −0.0198 (5) |
N1 | 0.0165 (5) | 0.0282 (6) | 0.0310 (6) | −0.0060 (4) | 0.0095 (5) | −0.0130 (5) |
C10 | 0.0162 (6) | 0.0236 (6) | 0.0326 (7) | −0.0020 (5) | 0.0041 (5) | −0.0117 (5) |
C13 | 0.0309 (10) | 0.124 (2) | 0.0852 (18) | −0.0340 (13) | 0.0318 (11) | −0.0861 (18) |
C12 | 0.0456 (12) | 0.0200 (9) | 0.1000 (19) | −0.0051 (8) | −0.0408 (12) | 0.0072 (10) |
C11 | 0.0187 (7) | 0.0249 (7) | 0.0235 (7) | 0.0011 (6) | 0.0039 (5) | −0.0004 (6) |
O2 | 0.0222 (5) | 0.0688 (9) | 0.0520 (7) | −0.0169 (5) | 0.0205 (5) | −0.0343 (6) |
Geometric parameters (Å, º) top
C9—C8 | 1.3888 (18) | C10—C11A | 1.515 (12) |
C9—C4 | 1.3995 (18) | C10—C11 | 1.5294 (19) |
C9—H9 | 0.93 | C10—C12A | 1.647 (14) |
C8—C7 | 1.389 (2) | C13—H13A | 0.96 |
C8—H8 | 0.93 | C13—H13B | 0.96 |
C7—C6 | 1.382 (2) | C13—H13C | 0.96 |
C7—H7 | 0.93 | C12—H12A | 0.96 |
C6—C5 | 1.3911 (19) | C12—H12B | 0.96 |
C6—H6 | 0.93 | C12—H12C | 0.96 |
C5—C4 | 1.4025 (17) | C11—O2 | 1.4287 (18) |
C5—H5 | 0.93 | C11—H11A | 0.97 |
C4—C3 | 1.4716 (17) | C11—H11B | 0.97 |
C3—C2 | 1.3325 (18) | C13A—H13D | 0.96 |
C3—H3 | 0.93 | C13A—H13E | 0.96 |
C2—C1 | 1.4869 (17) | C13A—H13F | 0.96 |
C2—H2 | 0.93 | C12A—H12D | 0.96 |
C1—O1 | 1.2433 (15) | C12A—H12E | 0.96 |
C1—N1 | 1.3327 (16) | C12A—H12F | 0.96 |
N1—C10 | 1.4863 (16) | C11A—O2 | 1.657 (13) |
N1—H1 | 0.92 (2) | C11A—H11C | 0.97 |
C10—C13A | 1.500 (12) | C11A—H11D | 0.97 |
C10—C12 | 1.514 (3) | O2—H2O | 0.90 (2) |
C10—C13 | 1.515 (2) | | |
| | | |
C8—C9—C4 | 120.31 (12) | C13A—C10—C12A | 112.3 (7) |
C8—C9—H9 | 119.8 | C11A—C10—C12A | 104.7 (7) |
C4—C9—H9 | 119.8 | C10—C13—H13A | 109.5 |
C7—C8—C9 | 120.42 (13) | C10—C13—H13B | 109.5 |
C7—C8—H8 | 119.8 | H13A—C13—H13B | 109.5 |
C9—C8—H8 | 119.8 | C10—C13—H13C | 109.5 |
C6—C7—C8 | 120.11 (13) | H13A—C13—H13C | 109.5 |
C6—C7—H7 | 119.9 | H13B—C13—H13C | 109.5 |
C8—C7—H7 | 119.9 | C10—C12—H12A | 109.5 |
C7—C6—C5 | 119.74 (13) | C10—C12—H12B | 109.5 |
C7—C6—H6 | 120.1 | H12A—C12—H12B | 109.5 |
C5—C6—H6 | 120.1 | C10—C12—H12C | 109.5 |
C6—C5—C4 | 120.96 (13) | H12A—C12—H12C | 109.5 |
C6—C5—H5 | 119.5 | H12B—C12—H12C | 109.5 |
C4—C5—H5 | 119.5 | O2—C11—C10 | 113.25 (12) |
C9—C4—C5 | 118.46 (12) | O2—C11—H11A | 108.9 |
C9—C4—C3 | 122.82 (11) | C10—C11—H11A | 108.9 |
C5—C4—C3 | 118.72 (11) | O2—C11—H11B | 108.9 |
C2—C3—C4 | 127.12 (12) | C10—C11—H11B | 108.9 |
C2—C3—H3 | 116.4 | H11A—C11—H11B | 107.7 |
C4—C3—H3 | 116.4 | C10—C13A—H13D | 109.5 |
C3—C2—C1 | 120.64 (12) | C10—C13A—H13E | 109.5 |
C3—C2—H2 | 119.7 | H13D—C13A—H13E | 109.5 |
C1—C2—H2 | 119.7 | C10—C13A—H13F | 109.5 |
O1—C1—N1 | 124.28 (12) | H13D—C13A—H13F | 109.5 |
O1—C1—C2 | 120.84 (11) | H13E—C13A—H13F | 109.5 |
N1—C1—C2 | 114.88 (11) | C10—C12A—H12D | 109.5 |
C1—N1—C10 | 128.32 (11) | C10—C12A—H12E | 109.5 |
C1—N1—H1 | 116.3 (12) | H12D—C12A—H12E | 109.5 |
C10—N1—H1 | 114.7 (12) | C10—C12A—H12F | 109.5 |
N1—C10—C13A | 103.2 (5) | H12D—C12A—H12F | 109.5 |
N1—C10—C12 | 108.77 (12) | H12E—C12A—H12F | 109.5 |
N1—C10—C13 | 105.93 (12) | C10—C11A—O2 | 102.2 (7) |
C12—C10—C13 | 111.95 (19) | C10—C11A—H11C | 111.3 |
N1—C10—C11A | 117.7 (5) | O2—C11A—H11C | 111.3 |
C13A—C10—C11A | 113.8 (7) | C10—C11A—H11D | 111.3 |
N1—C10—C11 | 112.62 (11) | O2—C11A—H11D | 111.3 |
C12—C10—C11 | 110.36 (14) | H11C—C11A—H11D | 109.2 |
C13—C10—C11 | 107.17 (15) | C11—O2—H2O | 103.1 (14) |
N1—C10—C12A | 105.1 (5) | C11A—O2—H2O | 89.0 (15) |
| | | |
C4—C9—C8—C7 | −0.79 (19) | C1—N1—C10—C11A | 28.7 (6) |
C9—C8—C7—C6 | −0.2 (2) | C1—N1—C10—C11 | −45.60 (19) |
C8—C7—C6—C5 | 1.0 (2) | C1—N1—C10—C12A | 144.6 (5) |
C7—C6—C5—C4 | −0.9 (2) | N1—C10—C11—O2 | 80.34 (15) |
C8—C9—C4—C5 | 0.92 (18) | C13A—C10—C11—O2 | 168.8 (7) |
C8—C9—C4—C3 | −178.18 (12) | C12—C10—C11—O2 | −41.42 (18) |
C6—C5—C4—C9 | −0.08 (19) | C13—C10—C11—O2 | −163.56 (15) |
C6—C5—C4—C3 | 179.06 (12) | C11A—C10—C11—O2 | −31.2 (5) |
C9—C4—C3—C2 | −9.2 (2) | C12A—C10—C11—O2 | −115.5 (8) |
C5—C4—C3—C2 | 171.75 (13) | N1—C10—C11A—O2 | −79.3 (7) |
C4—C3—C2—C1 | 178.09 (12) | C13A—C10—C11A—O2 | 41.5 (9) |
C3—C2—C1—O1 | −4.3 (2) | C12—C10—C11A—O2 | −168.7 (10) |
C3—C2—C1—N1 | 175.71 (12) | C13—C10—C11A—O2 | 115.9 (6) |
O1—C1—N1—C10 | 2.5 (2) | C11—C10—C11A—O2 | 24.9 (4) |
C2—C1—N1—C10 | −177.48 (12) | C12A—C10—C11A—O2 | 164.5 (7) |
C1—N1—C10—C13A | −97.5 (5) | C10—C11—O2—C11A | 28.7 (5) |
C1—N1—C10—C12 | 77.1 (2) | C10—C11A—O2—C11 | −27.1 (4) |
C1—N1—C10—C13 | −162.44 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.92 (2) | 1.98 (2) | 2.879 (2) | 165 (2) |
O2—H2O···O1 | 0.90 (2) | 1.72 (2) | 2.592 (2) | 161 (2) |
C9—H9···O1i | 0.93 | 2.80 | 3.491 (2) | 132 |
C2—H2···O2i | 0.93 | 2.73 | 3.396 (2) | 130 |
Symmetry code: (i) x−1, y, z. |
(
R,
S)-(2
E)-
N-(1-Hydroxy-3-methyl-butan-2-yl)-3-phenylprop-2-enamide (3)
top
Crystal data top
C14H19NO2 | F(000) = 1008 |
Mr = 233.3 | Dx = 1.158 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2ybc | Cell parameters from 12512 reflections |
a = 10.6921 (2) Å | θ = 3.7–71.6° |
b = 21.1761 (4) Å | µ = 0.61 mm−1 |
c = 11.8518 (2) Å | T = 298 K |
β = 94.198 (2)° | Irregular, colourless |
V = 2676.25 (8) Å3 | 0.73 × 0.53 × 0.30 mm |
Z = 8 | |
Data collection top
Rigaku Oxford Diffraction SuperNova Dual Source diffractometer with an
Atlas detector | 5186 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 4039 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.061 |
Detector resolution: 10.3756 pixels mm-1 | θmax = 71.6°, θmin = 4.2° |
ω scans | h = −13→13 |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015) | k = −26→26 |
Tmin = 0.896, Tmax = 0.959 | l = −13→14 |
38997 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(Fo2) + (0.059P)2 + 0.4891P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.130 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.17 e Å−3 |
5186 reflections | Δρmin = −0.15 e Å−3 |
358 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0069 (4) |
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 | Occ. (<1) |
C9A | 0.4826 (2) | 0.06663 (11) | 0.1217 (2) | 0.0904 (7) | |
H9A | 0.4067 | 0.0649 | 0.1553 | 0.109* | |
C8A | 0.4943 (3) | 0.10619 (13) | 0.0309 (3) | 0.1094 (9) | |
H8A | 0.4262 | 0.1304 | 0.0034 | 0.131* | |
C7A | 0.6045 (2) | 0.11010 (11) | −0.01883 (18) | 0.0906 (7) | |
H7A | 0.612 | 0.1368 | −0.0803 | 0.109* | |
C6A | 0.7032 (2) | 0.07500 (12) | 0.02167 (19) | 0.0951 (7) | |
H6A | 0.779 | 0.0776 | −0.0118 | 0.114* | |
C5A | 0.69189 (19) | 0.03520 (11) | 0.11273 (18) | 0.0830 (6) | |
H5A | 0.7609 | 0.0116 | 0.1402 | 0.1* | |
C4A | 0.58085 (14) | 0.02966 (8) | 0.16362 (13) | 0.0560 (4) | |
C3A | 0.56903 (14) | −0.01400 (8) | 0.25842 (13) | 0.0562 (4) | |
H3A | 0.6429 | −0.0264 | 0.2986 | 0.067* | |
C2A | 0.46380 (14) | −0.03718 (8) | 0.29181 (14) | 0.0564 (4) | |
H2A | 0.3897 | −0.0255 | 0.2512 | 0.068* | |
C1A | 0.45401 (13) | −0.08048 (7) | 0.38913 (13) | 0.0509 (3) | |
O1A | 0.54255 (10) | −0.09249 (6) | 0.45910 (10) | 0.0651 (3) | |
N1A | 0.34155 (11) | −0.10643 (6) | 0.39450 (11) | 0.0521 (3) | |
C10A | 0.30745 (13) | −0.14949 (7) | 0.48367 (12) | 0.0510 (4) | |
H10A | 0.3812 | −0.1753 | 0.5058 | 0.061* | |
C11A | 0.27590 (16) | −0.11149 (8) | 0.58644 (14) | 0.0616 (4) | |
H11A | 0.2639 | −0.1402 | 0.6485 | 0.074* | |
H11B | 0.3462 | −0.0843 | 0.6092 | 0.074* | |
O2A | 0.16675 (12) | −0.07394 (7) | 0.56665 (12) | 0.0735 (4) | |
C12A | 0.20377 (16) | −0.19384 (8) | 0.43680 (13) | 0.0613 (4) | |
H12A | 0.132 | −0.168 | 0.4088 | 0.074* | |
C13A | 0.1605 (2) | −0.23775 (11) | 0.52791 (17) | 0.0863 (6) | |
H13A | 0.2316 | −0.2595 | 0.5637 | 0.129* | |
H13B | 0.1022 | −0.268 | 0.4941 | 0.129* | |
H13C | 0.1203 | −0.2135 | 0.5834 | 0.129* | |
C14A | 0.2462 (3) | −0.23233 (12) | 0.33841 (19) | 0.1040 (8) | |
H14A | 0.3143 | −0.2593 | 0.3646 | 0.156* | |
H14B | 0.2733 | −0.2044 | 0.2813 | 0.156* | |
H14C | 0.1776 | −0.2576 | 0.3071 | 0.156* | |
C5B | −0.22800 (18) | −0.22068 (9) | 0.11562 (16) | 0.0696 (5) | |
H5B | −0.1728 | −0.2227 | 0.0586 | 0.084* | |
C6B | −0.3353 (2) | −0.25774 (9) | 0.10801 (18) | 0.0784 (6) | |
H6B | −0.3517 | −0.284 | 0.0457 | 0.094* | |
C7B | −0.4168 (2) | −0.25604 (10) | 0.1909 (2) | 0.0846 (6) | |
H7B | −0.4877 | −0.2816 | 0.1864 | 0.101* | |
C8B | −0.3934 (2) | −0.21616 (11) | 0.2813 (2) | 0.0898 (7) | |
H8B | −0.4498 | −0.2142 | 0.3373 | 0.108* | |
C9B | −0.28749 (18) | −0.17904 (10) | 0.28996 (16) | 0.0744 (5) | |
H9B | −0.273 | −0.1526 | 0.3521 | 0.089* | |
C4B | −0.20184 (15) | −0.18050 (7) | 0.20735 (14) | 0.0569 (4) | |
C3B | −0.08947 (14) | −0.14050 (8) | 0.21312 (13) | 0.0565 (4) | |
H3B | −0.0249 | −0.153 | 0.1696 | 0.068* | |
C2B | −0.07043 (14) | −0.08842 (8) | 0.27375 (13) | 0.0534 (4) | |
H2B | −0.1307 | −0.0755 | 0.3216 | 0.064* | |
C1B | 0.04471 (13) | −0.05045 (7) | 0.26690 (12) | 0.0492 (3) | |
O1B | 0.13900 (9) | −0.07156 (5) | 0.22576 (9) | 0.0588 (3) | |
N1B | 0.03887 (12) | 0.00890 (6) | 0.30693 (11) | 0.0532 (3) | |
C10B | 0.13869 (15) | 0.05532 (8) | 0.29841 (14) | 0.0592 (4) | |
H10B | 0.2136 | 0.0331 | 0.2766 | 0.071* | |
C11B | 0.16988 (17) | 0.08595 (8) | 0.41229 (15) | 0.0657 (4) | |
H11D | 0.2245 | 0.1219 | 0.4031 | 0.079* | |
H11C | 0.0934 | 0.1013 | 0.442 | 0.079* | |
O2B | 0.22988 (12) | 0.04271 (6) | 0.49042 (11) | 0.0718 (4) | |
C12B | 0.0994 (7) | 0.1046 (3) | 0.2031 (5) | 0.115 (2) | 0.745 (5) |
H12B | 0.1758 | 0.1292 | 0.1944 | 0.139* | 0.745 (5) |
C13B | 0.0141 (3) | 0.14755 (17) | 0.2236 (3) | 0.0909 (11) | 0.745 (5) |
H13D | −0.0667 | 0.1278 | 0.2239 | 0.136* | 0.745 (5) |
H13E | 0.0118 | 0.1794 | 0.1658 | 0.136* | 0.745 (5) |
H13F | 0.0352 | 0.1667 | 0.2959 | 0.136* | 0.745 (5) |
C14B | 0.0751 (9) | 0.0693 (4) | 0.0872 (7) | 0.155 (3) | 0.745 (5) |
H14E | 0.0054 | 0.041 | 0.0913 | 0.233* | 0.745 (5) |
H14F | 0.1485 | 0.0457 | 0.0714 | 0.233* | 0.745 (5) |
H14D | 0.0565 | 0.0995 | 0.028 | 0.233* | 0.745 (5) |
C12C | 0.1288 (5) | 0.1000 (7) | 0.2084 (11) | 0.052 (3) | 0.255 (5) |
H12C | 0.038 | 0.104 | 0.2132 | 0.063* | 0.255 (5) |
C13C | 0.1408 (11) | 0.1622 (4) | 0.1865 (8) | 0.100 (4) | 0.255 (5) |
H13G | 0.1119 | 0.1863 | 0.248 | 0.15* | 0.255 (5) |
H13H | 0.0917 | 0.1726 | 0.1179 | 0.15* | 0.255 (5) |
H13I | 0.2273 | 0.1718 | 0.1779 | 0.15* | 0.255 (5) |
C14C | 0.1121 (9) | 0.0725 (8) | 0.0950 (14) | 0.064 (3) | 0.255 (5) |
H14I | 0.1752 | 0.0409 | 0.0865 | 0.095* | 0.255 (5) |
H14G | 0.1195 | 0.105 | 0.0394 | 0.095* | 0.255 (5) |
H14H | 0.0306 | 0.0534 | 0.0846 | 0.095* | 0.255 (5) |
H1A | 0.2845 (15) | −0.0954 (8) | 0.3433 (15) | 0.055 (4)* | |
H2AO | 0.186 (2) | −0.0430 (12) | 0.531 (2) | 0.097 (8)* | |
H1B | −0.0304 (16) | 0.0214 (8) | 0.3342 (15) | 0.062 (5)* | |
H2BO | 0.310 (2) | 0.0554 (11) | 0.5045 (19) | 0.098 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C9A | 0.0697 (12) | 0.0884 (14) | 0.1145 (18) | 0.0072 (10) | 0.0158 (11) | 0.0372 (13) |
C8A | 0.0956 (16) | 0.0985 (17) | 0.132 (2) | 0.0027 (13) | −0.0052 (15) | 0.0521 (16) |
C7A | 0.1184 (18) | 0.0843 (14) | 0.0667 (12) | −0.0292 (13) | −0.0093 (12) | 0.0188 (11) |
C6A | 0.1011 (16) | 0.1092 (18) | 0.0780 (14) | −0.0135 (14) | 0.0273 (12) | 0.0203 (13) |
C5A | 0.0733 (12) | 0.1013 (15) | 0.0761 (13) | 0.0037 (11) | 0.0180 (10) | 0.0219 (11) |
C4A | 0.0562 (8) | 0.0613 (9) | 0.0501 (8) | −0.0089 (7) | 0.0015 (7) | −0.0013 (7) |
C3A | 0.0502 (8) | 0.0674 (10) | 0.0508 (9) | −0.0027 (7) | 0.0023 (6) | 0.0000 (7) |
C2A | 0.0483 (8) | 0.0659 (10) | 0.0549 (9) | −0.0007 (7) | 0.0026 (6) | 0.0025 (7) |
C1A | 0.0441 (7) | 0.0604 (9) | 0.0482 (8) | −0.0016 (6) | 0.0034 (6) | −0.0053 (7) |
O1A | 0.0501 (6) | 0.0851 (8) | 0.0588 (7) | −0.0085 (5) | −0.0056 (5) | 0.0080 (6) |
N1A | 0.0450 (6) | 0.0643 (8) | 0.0464 (7) | −0.0025 (6) | −0.0001 (5) | 0.0075 (6) |
C10A | 0.0489 (7) | 0.0595 (9) | 0.0443 (8) | −0.0007 (6) | 0.0008 (6) | 0.0045 (6) |
C11A | 0.0690 (10) | 0.0669 (10) | 0.0489 (9) | −0.0043 (8) | 0.0048 (7) | −0.0006 (7) |
O2A | 0.0728 (8) | 0.0693 (8) | 0.0821 (9) | 0.0035 (6) | 0.0315 (7) | 0.0048 (7) |
C12A | 0.0639 (9) | 0.0702 (10) | 0.0495 (9) | −0.0146 (8) | 0.0030 (7) | 0.0025 (8) |
C13A | 0.1076 (16) | 0.0847 (14) | 0.0680 (12) | −0.0346 (12) | 0.0162 (11) | 0.0023 (10) |
C14A | 0.144 (2) | 0.1022 (17) | 0.0689 (13) | −0.0545 (16) | 0.0305 (13) | −0.0279 (12) |
C5B | 0.0799 (12) | 0.0658 (10) | 0.0625 (11) | 0.0065 (9) | 0.0011 (9) | −0.0103 (8) |
C6B | 0.0892 (13) | 0.0634 (11) | 0.0791 (13) | −0.0001 (10) | −0.0172 (11) | −0.0180 (9) |
C7B | 0.0765 (12) | 0.0798 (13) | 0.0956 (15) | −0.0184 (10) | −0.0055 (11) | −0.0138 (11) |
C8B | 0.0791 (13) | 0.1038 (16) | 0.0879 (15) | −0.0276 (12) | 0.0167 (11) | −0.0185 (13) |
C9B | 0.0753 (11) | 0.0834 (12) | 0.0653 (11) | −0.0191 (10) | 0.0106 (9) | −0.0197 (9) |
C4B | 0.0608 (9) | 0.0550 (9) | 0.0543 (9) | 0.0009 (7) | −0.0007 (7) | −0.0029 (7) |
C3B | 0.0553 (8) | 0.0647 (10) | 0.0496 (8) | 0.0035 (7) | 0.0039 (6) | −0.0003 (7) |
C2B | 0.0472 (8) | 0.0637 (9) | 0.0492 (8) | 0.0023 (7) | 0.0028 (6) | −0.0006 (7) |
C1B | 0.0448 (7) | 0.0621 (9) | 0.0403 (7) | 0.0032 (6) | −0.0011 (6) | 0.0028 (6) |
O1B | 0.0498 (6) | 0.0693 (7) | 0.0577 (6) | 0.0036 (5) | 0.0067 (5) | −0.0023 (5) |
N1B | 0.0447 (7) | 0.0624 (8) | 0.0525 (7) | 0.0018 (6) | 0.0034 (5) | −0.0024 (6) |
C10B | 0.0611 (9) | 0.0580 (9) | 0.0590 (10) | −0.0028 (7) | 0.0083 (7) | 0.0043 (7) |
C11B | 0.0677 (10) | 0.0587 (10) | 0.0690 (11) | −0.0068 (8) | −0.0073 (8) | 0.0033 (8) |
O2B | 0.0635 (7) | 0.0723 (8) | 0.0767 (8) | −0.0135 (6) | −0.0150 (6) | 0.0137 (6) |
C12B | 0.215 (6) | 0.071 (3) | 0.059 (2) | 0.011 (4) | 0.002 (3) | 0.021 (2) |
C13B | 0.094 (2) | 0.089 (2) | 0.088 (2) | 0.0286 (17) | −0.0014 (16) | 0.0253 (16) |
C14B | 0.287 (9) | 0.122 (5) | 0.054 (3) | −0.007 (6) | −0.010 (5) | 0.017 (3) |
C12C | 0.010 (2) | 0.072 (6) | 0.075 (7) | 0.006 (2) | 0.005 (2) | 0.010 (4) |
C13C | 0.138 (9) | 0.074 (5) | 0.084 (6) | −0.042 (5) | −0.012 (5) | 0.027 (4) |
C14C | 0.048 (4) | 0.090 (8) | 0.054 (7) | 0.012 (4) | 0.011 (3) | 0.015 (5) |
Geometric parameters (Å, º) top
C9A—C4A | 1.374 (3) | C7B—C8B | 1.373 (3) |
C9A—C8A | 1.376 (3) | C7B—H7B | 0.93 |
C9A—H9A | 0.93 | C8B—C9B | 1.376 (3) |
C8A—C7A | 1.359 (3) | C8B—H8B | 0.93 |
C8A—H8A | 0.93 | C9B—C4B | 1.389 (2) |
C7A—C6A | 1.350 (3) | C9B—H9B | 0.93 |
C7A—H7A | 0.93 | C4B—C3B | 1.468 (2) |
C6A—C5A | 1.382 (3) | C3B—C2B | 1.324 (2) |
C6A—H6A | 0.93 | C3B—H3B | 0.93 |
C5A—C4A | 1.375 (2) | C2B—C1B | 1.478 (2) |
C5A—H5A | 0.93 | C2B—H2B | 0.93 |
C4A—C3A | 1.468 (2) | C1B—O1B | 1.2353 (17) |
C3A—C2A | 1.315 (2) | C1B—N1B | 1.347 (2) |
C3A—H3A | 0.93 | N1B—C10B | 1.460 (2) |
C2A—C1A | 1.483 (2) | N1B—H1B | 0.870 (18) |
C2A—H2A | 0.93 | C10B—C12C | 1.424 (13) |
C1A—O1A | 1.2383 (18) | C10B—C11B | 1.513 (2) |
C1A—N1A | 1.3279 (18) | C10B—C12B | 1.573 (6) |
N1A—C10A | 1.4621 (19) | C10B—H10B | 0.98 |
N1A—H1A | 0.861 (17) | C11B—O2B | 1.421 (2) |
C10A—C11A | 1.518 (2) | C11B—H11D | 0.97 |
C10A—C12A | 1.526 (2) | C11B—H11C | 0.97 |
C10A—H10A | 0.98 | O2B—H2BO | 0.90 (2) |
C11A—O2A | 1.417 (2) | C12B—C13B | 1.322 (7) |
C11A—H11A | 0.97 | C12B—C14B | 1.570 (11) |
C11A—H11B | 0.97 | C12B—H12B | 0.98 |
O2A—H2AO | 0.81 (2) | C13B—H13D | 0.96 |
C12A—C14A | 1.519 (3) | C13B—H13E | 0.96 |
C12A—C13A | 1.523 (2) | C13B—H13F | 0.96 |
C12A—H12A | 0.98 | C14B—H14E | 0.96 |
C13A—H13A | 0.96 | C14B—H14F | 0.96 |
C13A—H13B | 0.96 | C14B—H14D | 0.96 |
C13A—H13C | 0.96 | C12C—C13C | 1.350 (16) |
C14A—H14A | 0.96 | C12C—C14C | 1.46 (2) |
C14A—H14B | 0.96 | C12C—H12C | 0.98 |
C14A—H14C | 0.96 | C13C—H13G | 0.96 |
C5B—C6B | 1.388 (3) | C13C—H13H | 0.96 |
C5B—C4B | 1.393 (2) | C13C—H13I | 0.96 |
C5B—H5B | 0.93 | C14C—H14I | 0.96 |
C6B—C7B | 1.361 (3) | C14C—H14G | 0.96 |
C6B—H6B | 0.93 | C14C—H14H | 0.96 |
| | | |
C4A—C9A—C8A | 121.2 (2) | C7B—C8B—H8B | 119.6 |
C4A—C9A—H9A | 119.4 | C9B—C8B—H8B | 119.6 |
C8A—C9A—H9A | 119.4 | C8B—C9B—C4B | 121.06 (18) |
C7A—C8A—C9A | 120.5 (2) | C8B—C9B—H9B | 119.5 |
C7A—C8A—H8A | 119.7 | C4B—C9B—H9B | 119.5 |
C9A—C8A—H8A | 119.7 | C9B—C4B—C5B | 117.30 (16) |
C6A—C7A—C8A | 119.5 (2) | C9B—C4B—C3B | 122.28 (15) |
C6A—C7A—H7A | 120.3 | C5B—C4B—C3B | 120.39 (16) |
C8A—C7A—H7A | 120.3 | C2B—C3B—C4B | 126.79 (15) |
C7A—C6A—C5A | 120.2 (2) | C2B—C3B—H3B | 116.6 |
C7A—C6A—H6A | 119.9 | C4B—C3B—H3B | 116.6 |
C5A—C6A—H6A | 119.9 | C3B—C2B—C1B | 121.27 (15) |
C4A—C5A—C6A | 121.5 (2) | C3B—C2B—H2B | 119.4 |
C4A—C5A—H5A | 119.3 | C1B—C2B—H2B | 119.4 |
C6A—C5A—H5A | 119.3 | O1B—C1B—N1B | 122.49 (14) |
C9A—C4A—C5A | 117.04 (17) | O1B—C1B—C2B | 122.14 (14) |
C9A—C4A—C3A | 121.97 (16) | N1B—C1B—C2B | 115.36 (13) |
C5A—C4A—C3A | 120.99 (16) | C1B—N1B—C10B | 123.44 (13) |
C2A—C3A—C4A | 126.10 (15) | C1B—N1B—H1B | 118.5 (12) |
C2A—C3A—H3A | 117 | C10B—N1B—H1B | 117.8 (12) |
C4A—C3A—H3A | 117 | C12C—C10B—N1B | 119.0 (4) |
C3A—C2A—C1A | 125.14 (14) | C12C—C10B—C11B | 112.5 (6) |
C3A—C2A—H2A | 117.4 | N1B—C10B—C11B | 109.97 (13) |
C1A—C2A—H2A | 117.4 | N1B—C10B—C12B | 109.8 (3) |
O1A—C1A—N1A | 122.24 (15) | C11B—C10B—C12B | 112.7 (3) |
O1A—C1A—C2A | 123.63 (13) | N1B—C10B—H10B | 108.1 |
N1A—C1A—C2A | 114.13 (13) | C11B—C10B—H10B | 108.1 |
C1A—N1A—C10A | 124.57 (13) | C12B—C10B—H10B | 108.1 |
C1A—N1A—H1A | 116.9 (11) | O2B—C11B—C10B | 111.39 (14) |
C10A—N1A—H1A | 118.5 (11) | O2B—C11B—H11D | 109.4 |
N1A—C10A—C11A | 109.34 (13) | C10B—C11B—H11D | 109.4 |
N1A—C10A—C12A | 109.48 (12) | O2B—C11B—H11C | 109.4 |
C11A—C10A—C12A | 114.84 (13) | C10B—C11B—H11C | 109.4 |
N1A—C10A—H10A | 107.6 | H11D—C11B—H11C | 108 |
C11A—C10A—H10A | 107.6 | C11B—O2B—H2BO | 107.8 (15) |
C12A—C10A—H10A | 107.6 | C13B—C12B—C14B | 114.6 (6) |
O2A—C11A—C10A | 113.15 (13) | C13B—C12B—C10B | 118.4 (4) |
O2A—C11A—H11A | 108.9 | C14B—C12B—C10B | 109.3 (5) |
C10A—C11A—H11A | 108.9 | C13B—C12B—H12B | 104.3 |
O2A—C11A—H11B | 108.9 | C14B—C12B—H12B | 104.3 |
C10A—C11A—H11B | 108.9 | C10B—C12B—H12B | 104.3 |
H11A—C11A—H11B | 107.8 | C12B—C13B—H13D | 109.5 |
C11A—O2A—H2AO | 107.7 (16) | C12B—C13B—H13E | 109.5 |
C14A—C12A—C13A | 109.88 (17) | H13D—C13B—H13E | 109.5 |
C14A—C12A—C10A | 111.11 (15) | C12B—C13B—H13F | 109.5 |
C13A—C12A—C10A | 111.60 (14) | H13D—C13B—H13F | 109.5 |
C14A—C12A—H12A | 108 | H13E—C13B—H13F | 109.5 |
C13A—C12A—H12A | 108 | C12B—C14B—H14E | 109.5 |
C10A—C12A—H12A | 108 | C12B—C14B—H14F | 109.5 |
C12A—C13A—H13A | 109.5 | H14E—C14B—H14F | 109.5 |
C12A—C13A—H13B | 109.5 | C12B—C14B—H14D | 109.5 |
H13A—C13A—H13B | 109.5 | H14E—C14B—H14D | 109.5 |
C12A—C13A—H13C | 109.5 | H14F—C14B—H14D | 109.5 |
H13A—C13A—H13C | 109.5 | C13C—C12C—C10B | 142.1 (11) |
H13B—C13A—H13C | 109.5 | C13C—C12C—C14C | 102.6 (11) |
C12A—C14A—H14A | 109.5 | C10B—C12C—C14C | 114.9 (12) |
C12A—C14A—H14B | 109.5 | C13C—C12C—H12C | 92 |
H14A—C14A—H14B | 109.5 | C10B—C12C—H12C | 92 |
C12A—C14A—H14C | 109.5 | C14C—C12C—H12C | 92 |
H14A—C14A—H14C | 109.5 | C12C—C13C—H13G | 109.5 |
H14B—C14A—H14C | 109.5 | C12C—C13C—H13H | 109.5 |
C6B—C5B—C4B | 120.94 (18) | H13G—C13C—H13H | 109.5 |
C6B—C5B—H5B | 119.5 | C12C—C13C—H13I | 109.5 |
C4B—C5B—H5B | 119.5 | H13G—C13C—H13I | 109.5 |
C7B—C6B—C5B | 120.56 (18) | H13H—C13C—H13I | 109.5 |
C7B—C6B—H6B | 119.7 | C12C—C14C—H14I | 109.5 |
C5B—C6B—H6B | 119.7 | C12C—C14C—H14G | 109.5 |
C6B—C7B—C8B | 119.32 (19) | H14I—C14C—H14G | 109.5 |
C6B—C7B—H7B | 120.3 | C12C—C14C—H14H | 109.5 |
C8B—C7B—H7B | 120.3 | H14I—C14C—H14H | 109.5 |
C7B—C8B—C9B | 120.8 (2) | H14G—C14C—H14H | 109.5 |
| | | |
C4A—C9A—C8A—C7A | −0.7 (4) | C8B—C9B—C4B—C3B | 178.70 (19) |
C9A—C8A—C7A—C6A | −0.3 (4) | C6B—C5B—C4B—C9B | −0.2 (3) |
C8A—C7A—C6A—C5A | 0.3 (4) | C6B—C5B—C4B—C3B | −178.62 (16) |
C7A—C6A—C5A—C4A | 0.7 (4) | C9B—C4B—C3B—C2B | −19.6 (3) |
C8A—C9A—C4A—C5A | 1.6 (3) | C5B—C4B—C3B—C2B | 158.73 (17) |
C8A—C9A—C4A—C3A | −178.4 (2) | C4B—C3B—C2B—C1B | −176.51 (14) |
C6A—C5A—C4A—C9A | −1.6 (3) | C3B—C2B—C1B—O1B | −16.3 (2) |
C6A—C5A—C4A—C3A | 178.4 (2) | C3B—C2B—C1B—N1B | 162.66 (15) |
C9A—C4A—C3A—C2A | 21.2 (3) | O1B—C1B—N1B—C10B | 4.6 (2) |
C5A—C4A—C3A—C2A | −158.76 (19) | C2B—C1B—N1B—C10B | −174.39 (13) |
C4A—C3A—C2A—C1A | −178.95 (15) | C1B—N1B—C10B—C12C | 97.2 (6) |
C3A—C2A—C1A—O1A | 10.5 (3) | C1B—N1B—C10B—C11B | −130.90 (15) |
C3A—C2A—C1A—N1A | −168.58 (16) | C1B—N1B—C10B—C12B | 104.5 (3) |
O1A—C1A—N1A—C10A | 2.4 (2) | C12C—C10B—C11B—O2B | −155.3 (3) |
C2A—C1A—N1A—C10A | −178.53 (14) | N1B—C10B—C11B—O2B | 69.53 (18) |
C1A—N1A—C10A—C11A | 81.58 (18) | C12B—C10B—C11B—O2B | −167.6 (3) |
C1A—N1A—C10A—C12A | −151.81 (15) | C12C—C10B—C12B—C13B | −141 (4) |
N1A—C10A—C11A—O2A | 65.94 (17) | N1B—C10B—C12B—C13B | 73.9 (6) |
C12A—C10A—C11A—O2A | −57.56 (19) | C11B—C10B—C12B—C13B | −49.0 (7) |
N1A—C10A—C12A—C14A | 59.6 (2) | C12C—C10B—C12B—C14B | 86 (4) |
C11A—C10A—C12A—C14A | −176.94 (17) | N1B—C10B—C12B—C14B | −59.7 (5) |
N1A—C10A—C12A—C13A | −177.36 (15) | C11B—C10B—C12B—C14B | 177.3 (4) |
C11A—C10A—C12A—C13A | −53.9 (2) | N1B—C10B—C12C—C13C | 133.2 (10) |
C4B—C5B—C6B—C7B | −0.7 (3) | C11B—C10B—C12C—C13C | 2.5 (12) |
C5B—C6B—C7B—C8B | 1.4 (3) | C12B—C10B—C12C—C13C | 96 (4) |
C6B—C7B—C8B—C9B | −1.3 (4) | N1B—C10B—C12C—C14C | −55.5 (7) |
C7B—C8B—C9B—C4B | 0.4 (4) | C11B—C10B—C12C—C14C | 173.7 (5) |
C8B—C9B—C4B—C5B | 0.3 (3) | C12B—C10B—C12C—C14C | −93 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O1B | 0.86 (2) | 2.07 (2) | 2.933 (2) | 177 (2) |
O2A—H2AO···O2B | 0.81 (2) | 1.94 (3) | 2.732 (2) | 162 (2) |
C2B—H2B···O2Bi | 0.93 | 2.63 | 3.515 (2) | 159 |
N1B—H1B···O2Ai | 0.87 (2) | 2.24 (2) | 3.075 (2) | 162 (2) |
O2B—H2BO···O1Aii | 0.90 (2) | 1.79 (2) | 2.679 (2) | 170 (2) |
C3A—H3A···O2Bii | 0.93 | 2.78 | 3.594 (2) | 147 |
C6A—H6A···O1Biii | 0.93 | 2.75 | 3.489 (2) | 138 |
C9B—H9B···O1Aiv | 0.93 | 2.73 | 3.349 (2) | 124 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y, −z+1; (iii) −x+1, −y, −z; (iv) x−1, y, z. |