Cinnamamide pharmacophore for anti­convulsant activity: evidence from crystallographic studies

Żesławska, E.; Nitek, W.; Marona, H.; Gunia-Krzyżak, A.

doi:10.1107/S2053229618007660

Cinnamamide pharmacophore for anticonvulsant activity: evidence from crystallographic studies

E. Żesławska, W. Nitek, H. Marona and A. Gunia-Krzyżak

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)-(2E)-N-(2-hydroxybutyl)-3-phenylprop-2-enamide–water (3/1), C₁₃H₁₇NO₂·0.33H₂O, (1), (2E)-N-(1-hydroxy-2-methylpropan-2-yl)-3-phenylprop-2-enamide, C₁₃H₁₇NO₂, (2), and (R,S)-(2E)-N-(1-hydroxy-3-methyl-butan-2-yl)-3-phenylprop-2-enamide, C₁₄H₁₉NO₂, (3). Compound (1) crystallizes in the space group P $\overline{1}$ with three molecules in the asymmetric unit, whereas compounds (2) and (3) crystallize in the space group P2₁/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.

Keywords: pharmacophore; anticonvulsant activity; cinnamamide; crystal structure; hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618007660/qs3071sup1.cif Contains datablocks global, 1, 2, 3
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618007660/qs30711sup2.hkl Contains datablock 1
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618007660/qs30712sup3.hkl Contains datablock 2
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618007660/qs30713sup4.hkl Contains datablock 3
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618007660/qs30712sup5.cml Supplementary material

CCDC references: 1844810; 1844809; 1844808

Computing details top

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)-(2E)-N-(2-Hydroxybutyl)-3-phenylprop-2-enamide–water (3/1) (1) top

Crystal data top

3C₁₃H₁₇NO₂·H₂O	Z = 2
M_r = 675.84	F(000) = 728
Triclinic, P1	D_x = 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	R_int = 0.041
CCD scans	θ_max = 25.3°, θ_min = 2.6°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −10→10
T_min = 0.944, T_max = 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(F_o²) + (0.0469P)² + 1.5371P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
6667 reflections	Δρ_max = 0.73 e Å⁻³
474 parameters	Δρ_min = −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	U_iso*/U_eq
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···O^iv	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.

(2E)-N-(1-Hydroxy-2-methylpropan-2-yl)-3-phenylprop-2-enamide (2) top

Crystal data top

C₁₃H₁₇NO₂	F(000) = 472
M_r = 219.27	D_x = 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	R_int = 0.033
CCD scans	θ_max = 27.5°, θ_min = 2.8°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −7→7
T_min = 0.938, T_max = 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(F_o²) + (0.0561P)² + 0.4623P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.121	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.30 e Å⁻³
2753 reflections	Δρ_min = −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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)-(2E)-N-(1-Hydroxy-3-methyl-butan-2-yl)-3-phenylprop-2-enamide (3) top

Crystal data top

C₁₄H₁₉NO₂	F(000) = 1008
M_r = 233.3	D_x = 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	R_int = 0.061
Detector resolution: 10.3756 pixels mm^-1	θ_max = 71.6°, θ_min = 4.2°
ω scans	h = −13→13
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	k = −26→26
T_min = 0.896, T_max = 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(F_o²) + (0.059P)² + 0.4891P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.130	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.17 e Å⁻³
5186 reflections	Δρ_min = −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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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···O1A^iv	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.

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Cinnamamide pharmacophore for anti­convulsant activity: evidence from crystallographic studies

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Cinnamamide pharmacophore for anticonvulsant activity: evidence from crystallographic studies