The conformational analyses of 2-amino-N-[2-(di­methyl­phen­oxy)eth­yl]­propan-1-ol derivatives in different environments

Nitek, W.; Kania, A.; Marona, H.; Waszkielewicz, A.M.; Żesławska, E.

doi:10.1107/S2053229620008244

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The conformational analyses of 2-amino-N-[2-(dimethylphenoxy)ethyl]propan-1-ol derivatives in different environments

W. Nitek, A. Kania, H. Marona, A. M. Waszkielewicz and E. Żesławska

Four crystal structures of 2-amino-N-(dimethylphenoxyethyl)propan-1-ol derivatives, characterized by X-ray diffraction analysis, are reported. The free base (R,S)-2-amino-N-[2-(2,3-dimethylphenoxy)ethyl]propan-1-ol, C₁₃H₂₁NO₂, 1, crystallizes in the space group P2₁/n, with two independent molecules in the asymmetric unit. The hydrochloride, (S)-N-[2-(2,6-dimethylphenoxy)ethyl]-1-hydroxypropan-2-aminium chloride, C₁₃H₂₂NO₂⁺·Cl⁻, 2c, crystallizes in the space group P2₁, with one cation and one chloride anion in the asymmetric unit. The asymmetric unit of two salts of 2-picolinic acid, namely, (R,S)-N-[2-(2,3-dimethylphenoxy)ethyl]-1-hydroxypropan-2-aminium pyridine-2-carboxylate, C₁₃H₂₂NO₂⁺·C₆H₄NO₂⁻, 1p, and (R)-N-[2-(2,6-dimethylphenoxy)ethyl]-1-hydroxypropan-2-aminium pyridine-2-carboxylate, C₁₃H₂₂NO₂⁺·C₆H₄NO₂⁻, 2p, consists of one cation and one 2-picolinate anion. Salt 1p crystallizes in the triclinic centrosymmetric space group P $\overline 1$ , while salt 2p crystallizes in the space group P4₁2₁2. The conformations of the amine fragments are contrasted and that of 2p is found to have an unusual antiperiplanar arrangement about the ether group. The crystal packing of 1 and 2c is dominated by hydrogen-bonded chains, while the structures of the 2-picolinate salts have hydrogen-bonded rings as the major features. In both salts with 2-picolinic acid, the specific R₁²(5) hydrogen-bonding motif is observed. Structural studies have been enriched by the generation of fingerprint plots derived from Hirshfeld surfaces.

Keywords: aminoalkanol; 2-picolinic acid; crystal structure; hydrogen bonding; salts; anticonvulsant activity.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620008244/ky3196sup1.cif Contains datablocks global, 1, 1p, 2c, 2p
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229620008244/ky31961sup2.hkl Contains datablock 1
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229620008244/ky31961psup3.hkl Contains datablock 1p
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229620008244/ky31962csup4.hkl Contains datablock 2c
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229620008244/ky31962psup5.hkl Contains datablock 2p

CCDC references: 2011434; 2011435; 2011436; 2011437

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2018) for (1), (1p); CrysAlis PRO (Rigaku OD, 2019) for (2c); CrysAlis PRO (Rigaku OD, 2015) for (2p). Cell refinement: CrysAlis PRO (Rigaku OD, 2018) for (1), (1p); CrysAlis PRO (Rigaku OD, 2019) for (2c); CrysAlis PRO (Rigaku OD, 2015) for (2p). Data reduction: CrysAlis PRO (Rigaku OD, 2018) for (1), (1p); CrysAlis PRO (Rigaku OD, 2019) for (2c); CrysAlis PRO (Rigaku OD, 2015) for (2p). Program(s) used to refine structure: SIR2014 (Burla et al., 2015) and SHELXL2018 (Sheldrick, 2015) for (1), (1p), (2p); SIR2014 (Burla et al., 2015) and SHELXL2013 (Sheldrick, 2015) for (2c). Molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2020) for (1). Software used to prepare material for publication: publCIF (Westrip, 2010) for (1).

(R,S)-2-Amino-N-[2-(2,3-dimethylphenoxy)ethyl]propan-1-ol (1) top

Crystal data top

C₁₃H₂₁NO₂	F(000) = 976
M_r = 223.31	D_x = 1.141 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 16084 reflections
a = 7.2657 (1) Å	θ = 3.1–76.3°
b = 14.4917 (2) Å	µ = 0.60 mm⁻¹
c = 24.6836 (3) Å	T = 100 K
β = 90.042 (1)°	Prism, colourless
V = 2598.99 (6) Å³	0.47 × 0.20 × 0.06 mm
Z = 8

Data collection top

Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector	5363 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	4898 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.040
ω scans	θ_max = 76.6°, θ_min = 3.5°
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018)	h = −7→9
T_min = 0.471, T_max = 1	k = −18→17
32612 measured reflections	l = −28→31

Refinement top

Refinement on F²	9 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.153	w = 1/[σ²(F_o²) + (0.0751P)² + 1.2737P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
5363 reflections	Δρ_max = 0.28 e Å⁻³
322 parameters	Δρ_min = −0.23 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	Occ. (<1)
C1A	0.0437 (2)	0.44012 (12)	0.08125 (7)	0.0283 (4)	0.937 (2)
H1A	−0.017969	0.469564	0.050963	0.034*	0.937 (2)
H1B	0.080371	0.378679	0.070021	0.034*	0.937 (2)
C1B	0.0377 (2)	0.23282 (11)	0.57341 (6)	0.0293 (3)
H1C	−0.029734	0.257527	0.54273	0.035*
H1D	0.070304	0.169437	0.565213	0.035*
C2A	0.2128 (2)	0.49546 (11)	0.09665 (7)	0.0259 (4)	0.937 (2)
H2A	0.174425	0.556055	0.110177	0.031*	0.937 (2)
C3A	0.3365 (2)	0.50848 (12)	0.04764 (7)	0.0309 (4)	0.937 (2)
H3A	0.445413	0.541443	0.058202	0.046*	0.937 (2)
H3B	0.271996	0.542956	0.020387	0.046*	0.937 (2)
H3C	0.370415	0.449248	0.033356	0.046*	0.937 (2)
C2B	0.2115 (2)	0.28892 (10)	0.58219 (6)	0.0272 (3)
H2B	0.177314	0.352758	0.590561	0.033*
C3B	0.3300 (2)	0.28811 (13)	0.53161 (7)	0.0347 (4)
H3E	0.262973	0.315172	0.502091	0.052*
H3F	0.361896	0.225644	0.522679	0.052*
H3D	0.44022	0.322989	0.538053	0.052*
C4A	0.4648 (2)	0.49825 (11)	0.16247 (6)	0.0298 (3)
H4A	0.427945	0.56206	0.167278	0.036*
H4B	0.566169	0.496925	0.136924	0.036*
C4B	0.4640 (2)	0.30650 (11)	0.64744 (6)	0.0274 (3)
H4C	0.423967	0.370092	0.650823	0.033*
H4D	0.561817	0.304299	0.620741	0.033*
C5A	0.5281 (2)	0.45975 (11)	0.21589 (6)	0.0298 (3)
H5A	0.559086	0.394954	0.212142	0.036*
H5B	0.636312	0.492605	0.22849	0.036*
C5B	0.5361 (2)	0.27327 (11)	0.70108 (6)	0.0271 (3)
H5C	0.573069	0.209089	0.698585	0.033*
H5D	0.641869	0.309592	0.712059	0.033*
C6A	0.4179 (2)	0.46251 (10)	0.30764 (6)	0.0249 (3)
C6B	0.4295 (2)	0.27122 (10)	0.79312 (6)	0.0241 (3)
C7A	0.2797 (2)	0.49223 (10)	0.34341 (6)	0.0252 (3)
C7B	0.29152 (19)	0.29757 (10)	0.82965 (6)	0.0245 (3)
C8A	0.3122 (2)	0.48768 (10)	0.39894 (6)	0.0272 (3)
C8B	0.3259 (2)	0.29009 (10)	0.88502 (6)	0.0278 (3)
C9A	0.4805 (2)	0.45377 (10)	0.41815 (6)	0.0290 (3)
H9A	0.50269	0.451559	0.455242	0.035*
C9B	0.4956 (2)	0.25635 (11)	0.90307 (6)	0.0300 (3)
H9B	0.518673	0.251999	0.940045	0.036*
C10A	0.6141 (2)	0.42354 (10)	0.38239 (7)	0.0304 (3)
H10A	0.724839	0.400651	0.395678	0.036*
C10B	0.6294 (2)	0.22940 (10)	0.86651 (7)	0.0294 (3)
H10B	0.741239	0.20659	0.87906	0.035*
C11A	0.5845 (2)	0.42701 (10)	0.32713 (6)	0.0286 (3)
H11A	0.673987	0.406044	0.303196	0.034*
C11B	0.5977 (2)	0.23621 (10)	0.81134 (6)	0.0271 (3)
H11B	0.687273	0.217716	0.786715	0.033*
C12A	0.0995 (2)	0.52835 (12)	0.32150 (7)	0.0314 (3)
H12A	0.10157	0.526442	0.282632	0.047*
H12B	0.000278	0.490737	0.334622	0.047*
H12C	0.081921	0.590846	0.333327	0.047*
C12B	0.1104 (2)	0.33463 (12)	0.80889 (6)	0.0311 (3)
H12F	0.097151	0.397928	0.819671	0.047*
H12E	0.011195	0.298949	0.823729	0.047*
H12D	0.107794	0.330564	0.770078	0.047*
C13A	0.1679 (2)	0.51892 (13)	0.43868 (7)	0.0371 (4)
H13A	0.213114	0.511005	0.474937	0.056*
H13B	0.140245	0.582854	0.432564	0.056*
H13C	0.058323	0.482803	0.433874	0.056*
C13B	0.1824 (2)	0.31923 (13)	0.92566 (7)	0.0369 (4)
H13F	0.071194	0.284964	0.919577	0.055*
H13E	0.157879	0.383965	0.921653	0.055*
H13D	0.226704	0.307306	0.961637	0.055*
N1A	0.30906 (17)	0.44523 (8)	0.14022 (5)	0.0249 (3)
N1B	0.30906 (16)	0.24925 (8)	0.62906 (5)	0.0233 (3)
O1A	−0.07903 (17)	0.43371 (9)	0.12559 (7)	0.0317 (3)	0.937 (2)
H1AO	−0.124 (3)	0.3775 (8)	0.1272 (8)	0.038*	0.937
O1B	−0.07491 (15)	0.23508 (8)	0.61988 (5)	0.0314 (3)
O2A	0.37972 (14)	0.47099 (8)	0.25351 (4)	0.0297 (3)
O2B	0.38951 (14)	0.28358 (8)	0.73942 (4)	0.0281 (3)
C2A'	0.260 (3)	0.4638 (13)	0.0820 (5)	0.0259 (4)	0.063 (2)
H2C	0.36452	0.443115	0.059958	0.031*	0.063 (2)
C1A'	0.094 (3)	0.4051 (17)	0.0656 (10)	0.0283 (4)	0.063 (2)
H1E	0.059834	0.417457	0.028268	0.034*	0.063 (2)
H1F	0.122249	0.33995	0.069077	0.034*	0.063 (2)
O1A'	−0.053 (3)	0.4295 (15)	0.1010 (10)	0.0317 (3)	0.063 (2)
H1CO	−0.095795	0.374365	0.109869	0.038*	0.063 (2)
C3A'	0.232 (4)	0.5658 (13)	0.0699 (10)	0.0309 (4)	0.063 (2)
H3I	0.143999	0.590939	0.094999	0.046*	0.063 (2)
H3H	0.186155	0.572848	0.033633	0.046*	0.063 (2)
H3G	0.346541	0.59786	0.073532	0.046*	0.063 (2)
H1AN	0.227 (3)	0.4385 (15)	0.1683 (8)	0.043 (5)*
H1BN	0.226 (3)	0.2480 (14)	0.6565 (8)	0.035 (5)*
H1BO	−0.119 (3)	0.1775 (17)	0.6252 (9)	0.048 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.0260 (9)	0.0252 (9)	0.0339 (9)	−0.0010 (7)	−0.0024 (7)	0.0015 (7)
C1B	0.0290 (8)	0.0291 (8)	0.0298 (8)	−0.0023 (6)	−0.0020 (6)	0.0009 (6)
C2A	0.0263 (8)	0.0190 (7)	0.0323 (8)	0.0007 (6)	0.0004 (6)	−0.0002 (6)
C3A	0.0321 (9)	0.0287 (8)	0.0320 (8)	−0.0027 (6)	0.0005 (6)	0.0047 (6)
C2B	0.0268 (7)	0.0245 (7)	0.0304 (8)	−0.0011 (6)	−0.0011 (6)	0.0023 (6)
C3B	0.0332 (8)	0.0398 (9)	0.0310 (8)	−0.0044 (7)	0.0003 (6)	0.0064 (7)
C4A	0.0258 (7)	0.0297 (8)	0.0340 (8)	−0.0070 (6)	−0.0002 (6)	−0.0031 (6)
C4B	0.0255 (7)	0.0263 (7)	0.0305 (8)	−0.0044 (6)	−0.0001 (6)	−0.0013 (6)
C5A	0.0222 (7)	0.0337 (8)	0.0334 (8)	−0.0023 (6)	0.0009 (6)	−0.0054 (6)
C5B	0.0208 (7)	0.0301 (8)	0.0304 (8)	0.0001 (6)	0.0010 (6)	−0.0037 (6)
C6A	0.0230 (7)	0.0201 (7)	0.0315 (8)	−0.0023 (5)	−0.0032 (6)	−0.0024 (5)
C6B	0.0231 (7)	0.0205 (7)	0.0286 (7)	−0.0034 (5)	−0.0029 (5)	−0.0015 (5)
C7A	0.0219 (7)	0.0196 (6)	0.0341 (8)	−0.0021 (5)	−0.0016 (6)	−0.0003 (5)
C7B	0.0223 (7)	0.0198 (6)	0.0314 (8)	−0.0026 (5)	−0.0012 (5)	−0.0001 (5)
C8A	0.0266 (7)	0.0212 (7)	0.0338 (8)	−0.0029 (6)	−0.0004 (6)	−0.0001 (6)
C8B	0.0288 (7)	0.0224 (7)	0.0321 (8)	−0.0038 (6)	0.0003 (6)	0.0002 (6)
C9A	0.0315 (8)	0.0247 (7)	0.0308 (8)	−0.0020 (6)	−0.0062 (6)	0.0015 (6)
C9B	0.0343 (8)	0.0269 (7)	0.0288 (8)	−0.0015 (6)	−0.0062 (6)	0.0030 (6)
C10A	0.0256 (7)	0.0234 (7)	0.0422 (9)	0.0018 (6)	−0.0074 (6)	0.0008 (6)
C10B	0.0271 (8)	0.0227 (7)	0.0384 (8)	0.0011 (6)	−0.0078 (6)	0.0013 (6)
C11A	0.0243 (7)	0.0231 (7)	0.0385 (8)	0.0019 (6)	−0.0021 (6)	−0.0046 (6)
C11B	0.0239 (7)	0.0221 (7)	0.0353 (8)	0.0019 (5)	−0.0016 (6)	−0.0029 (6)
C12A	0.0233 (7)	0.0346 (8)	0.0362 (8)	0.0025 (6)	−0.0015 (6)	0.0009 (6)
C12B	0.0241 (7)	0.0358 (8)	0.0334 (8)	0.0020 (6)	−0.0001 (6)	0.0004 (6)
C13A	0.0343 (9)	0.0429 (10)	0.0341 (8)	0.0027 (7)	0.0018 (7)	−0.0002 (7)
C13B	0.0353 (9)	0.0432 (10)	0.0321 (8)	0.0028 (7)	0.0023 (7)	−0.0008 (7)
N1A	0.0233 (6)	0.0232 (6)	0.0281 (6)	−0.0039 (5)	−0.0002 (5)	−0.0001 (5)
N1B	0.0218 (6)	0.0222 (6)	0.0259 (6)	−0.0016 (5)	0.0007 (5)	0.0002 (5)
O1A	0.0257 (6)	0.0242 (6)	0.0452 (8)	−0.0028 (5)	0.0053 (6)	−0.0016 (6)
O1B	0.0261 (5)	0.0266 (6)	0.0416 (6)	−0.0024 (4)	0.0043 (4)	−0.0009 (5)
O2A	0.0225 (5)	0.0371 (6)	0.0295 (6)	0.0006 (4)	−0.0012 (4)	−0.0036 (4)
O2B	0.0219 (5)	0.0358 (6)	0.0267 (5)	0.0031 (4)	−0.0011 (4)	−0.0025 (4)
C2A'	0.0263 (8)	0.0190 (7)	0.0323 (8)	0.0007 (6)	0.0004 (6)	−0.0002 (6)
C1A'	0.0260 (9)	0.0252 (9)	0.0339 (9)	−0.0010 (7)	−0.0024 (7)	0.0015 (7)
O1A'	0.0257 (6)	0.0242 (6)	0.0452 (8)	−0.0028 (5)	0.0053 (6)	−0.0016 (6)
C3A'	0.0321 (9)	0.0287 (8)	0.0320 (8)	−0.0027 (6)	0.0005 (6)	0.0047 (6)

Geometric parameters (Å, º) top

C1A—O1A	1.415 (2)	C7B—C12B	1.510 (2)
C1A—C2A	1.516 (2)	C8A—C9A	1.400 (2)
C1A—H1A	0.97	C8A—C13A	1.506 (2)
C1A—H1B	0.97	C8B—C9B	1.399 (2)
C1B—O1B	1.4098 (19)	C8B—C13B	1.508 (2)
C1B—C2B	1.517 (2)	C9A—C10A	1.383 (2)
C1B—H1C	0.97	C9A—H9A	0.93
C1B—H1D	0.97	C9B—C10B	1.383 (2)
C2A—N1A	1.4746 (19)	C9B—H9B	0.93
C2A—C3A	1.520 (2)	C10A—C11A	1.382 (2)
C2A—H2A	0.98	C10A—H10A	0.93
C3A—H3A	0.96	C10B—C11B	1.385 (2)
C3A—H3B	0.96	C10B—H10B	0.93
C3A—H3C	0.96	C11A—H11A	0.93
C2B—N1B	1.4731 (19)	C11B—H11B	0.93
C2B—C3B	1.517 (2)	C12A—H12A	0.96
C2B—H2B	0.98	C12A—H12B	0.96
C3B—H3E	0.96	C12A—H12C	0.96
C3B—H3F	0.96	C12B—H12F	0.96
C3B—H3D	0.96	C12B—H12E	0.96
C4A—N1A	1.4736 (18)	C12B—H12D	0.96
C4A—C5A	1.504 (2)	C13A—H13A	0.96
C4A—H4A	0.97	C13A—H13B	0.96
C4A—H4B	0.97	C13A—H13C	0.96
C4B—N1B	1.4701 (18)	C13B—H13F	0.96
C4B—C5B	1.503 (2)	C13B—H13E	0.96
C4B—H4C	0.97	C13B—H13D	0.96
C4B—H4D	0.97	N1A—C2A'	1.504 (10)
C5A—O2A	1.4328 (18)	N1A—H1AN	0.92 (2)
C5A—H5A	0.97	N1B—H1BN	0.91 (2)
C5A—H5B	0.97	O1A—H1AO	0.878 (10)
C5B—O2B	1.4332 (17)	O1B—H1BO	0.90 (2)
C5B—H5C	0.97	C2A'—C3A'	1.522 (10)
C5B—H5D	0.97	C2A'—C1A'	1.534 (10)
C6A—O2A	1.3701 (18)	C2A'—H2C	0.98
C6A—C11A	1.400 (2)	C1A'—O1A'	1.424 (10)
C6A—C7A	1.405 (2)	C1A'—H1E	0.97
C6B—O2B	1.3686 (18)	C1A'—H1F	0.97
C6B—C11B	1.397 (2)	O1A'—H1CO	0.8847
C6B—C7B	1.402 (2)	C3A'—H3I	0.96
C7A—C8A	1.392 (2)	C3A'—H3H	0.96
C7A—C12A	1.510 (2)	C3A'—H3G	0.96
C7B—C8B	1.393 (2)

O1A—C1A—C2A	110.60 (14)	C7B—C8B—C13B	120.47 (14)
O1A—C1A—H1A	109.5	C9B—C8B—C13B	119.71 (14)
C2A—C1A—H1A	109.5	C10A—C9A—C8A	120.52 (14)
O1A—C1A—H1B	109.5	C10A—C9A—H9A	119.7
C2A—C1A—H1B	109.5	C8A—C9A—H9A	119.7
H1A—C1A—H1B	108.1	C10B—C9B—C8B	120.71 (14)
O1B—C1B—C2B	110.77 (12)	C10B—C9B—H9B	119.6
O1B—C1B—H1C	109.5	C8B—C9B—H9B	119.6
C2B—C1B—H1C	109.5	C11A—C10A—C9A	120.64 (14)
O1B—C1B—H1D	109.5	C11A—C10A—H10A	119.7
C2B—C1B—H1D	109.5	C9A—C10A—H10A	119.7
H1C—C1B—H1D	108.1	C9B—C10B—C11B	120.34 (14)
N1A—C2A—C1A	107.80 (12)	C9B—C10B—H10B	119.8
N1A—C2A—C3A	111.18 (13)	C11B—C10B—H10B	119.8
C1A—C2A—C3A	110.25 (14)	C10A—C11A—C6A	119.11 (14)
N1A—C2A—H2A	109.2	C10A—C11A—H11A	120.4
C1A—C2A—H2A	109.2	C6A—C11A—H11A	120.4
C3A—C2A—H2A	109.2	C10B—C11B—C6B	119.15 (14)
C2A—C3A—H3A	109.5	C10B—C11B—H11B	120.4
C2A—C3A—H3B	109.5	C6B—C11B—H11B	120.4
H3A—C3A—H3B	109.5	C7A—C12A—H12A	109.5
C2A—C3A—H3C	109.5	C7A—C12A—H12B	109.5
H3A—C3A—H3C	109.5	H12A—C12A—H12B	109.5
H3B—C3A—H3C	109.5	C7A—C12A—H12C	109.5
N1B—C2B—C3B	111.72 (13)	H12A—C12A—H12C	109.5
N1B—C2B—C1B	107.65 (12)	H12B—C12A—H12C	109.5
C3B—C2B—C1B	110.55 (13)	C7B—C12B—H12F	109.5
N1B—C2B—H2B	109	C7B—C12B—H12E	109.5
C3B—C2B—H2B	109	H12F—C12B—H12E	109.5
C1B—C2B—H2B	109	C7B—C12B—H12D	109.5
C2B—C3B—H3E	109.5	H12F—C12B—H12D	109.5
C2B—C3B—H3F	109.5	H12E—C12B—H12D	109.5
H3E—C3B—H3F	109.5	C8A—C13A—H13A	109.5
C2B—C3B—H3D	109.5	C8A—C13A—H13B	109.5
H3E—C3B—H3D	109.5	H13A—C13A—H13B	109.5
H3F—C3B—H3D	109.5	C8A—C13A—H13C	109.5
N1A—C4A—C5A	111.57 (12)	H13A—C13A—H13C	109.5
N1A—C4A—H4A	109.3	H13B—C13A—H13C	109.5
C5A—C4A—H4A	109.3	C8B—C13B—H13F	109.5
N1A—C4A—H4B	109.3	C8B—C13B—H13E	109.5
C5A—C4A—H4B	109.3	H13F—C13B—H13E	109.5
H4A—C4A—H4B	108	C8B—C13B—H13D	109.5
N1B—C4B—C5B	110.93 (12)	H13F—C13B—H13D	109.5
N1B—C4B—H4C	109.5	H13E—C13B—H13D	109.5
C5B—C4B—H4C	109.5	C4A—N1A—C2A	112.21 (12)
N1B—C4B—H4D	109.5	C4A—N1A—C2A'	116.3 (7)
C5B—C4B—H4D	109.5	C4A—N1A—H1AN	105.7 (13)
H4C—C4B—H4D	108	C2A—N1A—H1AN	107.3 (13)
O2A—C5A—C4A	107.23 (12)	C2A'—N1A—H1AN	126.1 (16)
O2A—C5A—H5A	110.3	C4B—N1B—C2B	112.96 (11)
C4A—C5A—H5A	110.3	C4B—N1B—H1BN	106.8 (13)
O2A—C5A—H5B	110.3	C2B—N1B—H1BN	106.1 (13)
C4A—C5A—H5B	110.3	C1A—O1A—H1AO	109.3 (14)
H5A—C5A—H5B	108.5	C1B—O1B—H1BO	107.7 (14)
O2B—C5B—C4B	106.84 (12)	C6A—O2A—C5A	118.02 (11)
O2B—C5B—H5C	110.4	C6B—O2B—C5B	117.94 (11)
C4B—C5B—H5C	110.4	N1A—C2A'—C3A'	113.1 (15)
O2B—C5B—H5D	110.4	N1A—C2A'—C1A'	109.8 (14)
C4B—C5B—H5D	110.4	C3A'—C2A'—C1A'	112.3 (18)
H5C—C5B—H5D	108.6	N1A—C2A'—H2C	107.1
O2A—C6A—C11A	122.86 (13)	C3A'—C2A'—H2C	107.1
O2A—C6A—C7A	116.16 (13)	C1A'—C2A'—H2C	107.1
C11A—C6A—C7A	120.98 (14)	O1A'—C1A'—C2A'	107 (2)
O2B—C6B—C11B	122.97 (13)	O1A'—C1A'—H1E	110.3
O2B—C6B—C7B	115.83 (12)	C2A'—C1A'—H1E	110.3
C11B—C6B—C7B	121.19 (14)	O1A'—C1A'—H1F	110.3
C8A—C7A—C6A	118.91 (13)	C2A'—C1A'—H1F	110.3
C8A—C7A—C12A	121.02 (13)	H1E—C1A'—H1F	108.6
C6A—C7A—C12A	120.08 (13)	C1A'—O1A'—H1CO	101
C8B—C7B—C6B	118.80 (13)	C2A'—C3A'—H3I	109.5
C8B—C7B—C12B	121.06 (13)	C2A'—C3A'—H3H	109.5
C6B—C7B—C12B	120.13 (13)	H3I—C3A'—H3H	109.5
C7A—C8A—C9A	119.82 (14)	C2A'—C3A'—H3G	109.5
C7A—C8A—C13A	120.63 (14)	H3I—C3A'—H3G	109.5
C9A—C8A—C13A	119.55 (14)	H3H—C3A'—H3G	109.5
C7B—C8B—C9B	119.81 (14)

O1A—C1A—C2A—N1A	62.95 (17)	C8A—C9A—C10A—C11A	0.6 (2)
O1A—C1A—C2A—C3A	−175.52 (13)	C8B—C9B—C10B—C11B	0.6 (2)
O1B—C1B—C2B—N1B	59.04 (16)	C9A—C10A—C11A—C6A	0.7 (2)
O1B—C1B—C2B—C3B	−178.67 (12)	O2A—C6A—C11A—C10A	177.98 (13)
N1A—C4A—C5A—O2A	−64.22 (16)	C7A—C6A—C11A—C10A	−1.6 (2)
N1B—C4B—C5B—O2B	−62.68 (15)	C9B—C10B—C11B—C6B	0.4 (2)
O2A—C6A—C7A—C8A	−178.31 (12)	O2B—C6B—C11B—C10B	177.44 (13)
C11A—C6A—C7A—C8A	1.3 (2)	C7B—C6B—C11B—C10B	−1.4 (2)
O2A—C6A—C7A—C12A	1.7 (2)	C5A—C4A—N1A—C2A	164.20 (13)
C11A—C6A—C7A—C12A	−178.66 (13)	C5A—C4A—N1A—C2A'	−167.2 (11)
O2B—C6B—C7B—C8B	−177.60 (12)	C1A—C2A—N1A—C4A	−173.65 (13)
C11B—C6B—C7B—C8B	1.3 (2)	C3A—C2A—N1A—C4A	65.41 (17)
O2B—C6B—C7B—C12B	1.5 (2)	C5B—C4B—N1B—C2B	169.21 (12)
C11B—C6B—C7B—C12B	−179.60 (13)	C3B—C2B—N1B—C4B	67.95 (16)
C6A—C7A—C8A—C9A	−0.1 (2)	C1B—C2B—N1B—C4B	−170.49 (12)
C12A—C7A—C8A—C9A	179.91 (14)	C11A—C6A—O2A—C5A	−12.2 (2)
C6A—C7A—C8A—C13A	179.94 (14)	C7A—C6A—O2A—C5A	167.43 (13)
C12A—C7A—C8A—C13A	−0.1 (2)	C4A—C5A—O2A—C6A	−164.14 (12)
C6B—C7B—C8B—C9B	−0.3 (2)	C11B—C6B—O2B—C5B	−9.6 (2)
C12B—C7B—C8B—C9B	−179.38 (14)	C7B—C6B—O2B—C5B	169.23 (12)
C6B—C7B—C8B—C13B	178.95 (14)	C4B—C5B—O2B—C6B	−170.18 (12)
C12B—C7B—C8B—C13B	−0.2 (2)	C4A—N1A—C2A'—C3A'	−52 (2)
C7A—C8A—C9A—C10A	−0.9 (2)	C4A—N1A—C2A'—C1A'	−178.7 (13)
C13A—C8A—C9A—C10A	179.12 (14)	N1A—C2A'—C1A'—O1A'	59 (2)
C7B—C8B—C9B—C10B	−0.6 (2)	C3A'—C2A'—C1A'—O1A'	−68 (2)
C13B—C8B—C9B—C10B	−179.87 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1AO···N1Bⁱ	0.88 (1)	1.90 (1)	2.775 (2)	173 (2)
O1A′—H1CO···N1Bⁱ	0.88	1.98	2.86 (2)	180
O1B—H1BO···N1Aⁱⁱ	0.90 (2)	1.89 (2)	2.791 (2)	174 (2)

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x−1/2, −y+1/2, z+1/2.

(R,S)-N-[2-(2,3-Dimethylphenoxy)ethyl]-1-hydroxypropan-2-aminium pyridine-2-carboxylate (1p) top

Crystal data top

C₁₃H₂₂NO₂⁺·C₆H₄NO₂⁻	Z = 2
M_r = 346.42	F(000) = 372
Triclinic, P1	D_x = 1.264 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 6.5225 (1) Å	Cell parameters from 12551 reflections
b = 12.7734 (2) Å	θ = 4.0–76.5°
c = 12.8431 (2) Å	µ = 0.72 mm⁻¹
α = 118.954 (1)°	T = 100 K
β = 91.292 (1)°	Prism, clear colourless
γ = 101.139 (1)°	0.41 × 0.08 × 0.04 mm
V = 910.20 (3) Å³

Data collection top

Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector	3673 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	3310 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.043
ω scans	θ_max = 76.2°, θ_min = 4.0°
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018)	h = −7→8
T_min = 0.553, T_max = 1	k = −16→15
23149 measured reflections	l = −16→16

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)] = 0.035	w = 1/[σ²(F_o²) + (0.045P)² + 0.2207P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.094	(Δ/σ)_max = 0.003
S = 1.05	Δρ_max = 0.22 e Å⁻³
3673 reflections	Δρ_min = −0.18 e Å⁻³
275 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
11 restraints	Extinction coefficient: 0.0035 (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)
C1A	0.5082 (7)	0.4534 (6)	0.1194 (7)	0.0322 (15)	0.603 (3)
H1A	0.523554	0.409079	0.032992	0.039*	0.603 (3)
H1C	0.444424	0.391328	0.141577	0.039*	0.603 (3)
C3A	0.8233 (12)	0.6299 (5)	0.1739 (7)	0.041 (2)	0.603 (3)
H3A	0.738044	0.691348	0.206	0.062*	0.603 (3)
H3C	0.825283	0.60042	0.087936	0.062*	0.603 (3)
H3E	0.967705	0.66735	0.215976	0.062*	0.603 (3)
O1A	0.3675 (3)	0.53307 (18)	0.13754 (15)	0.0470 (5)	0.603 (3)
C1B	0.8094 (17)	0.6338 (7)	0.1823 (10)	0.037 (3)	0.397 (3)
H1B	0.949504	0.677605	0.231335	0.045*	0.397 (3)
H1D	0.826909	0.608723	0.097671	0.045*	0.397 (3)
C3B	0.5195 (15)	0.4421 (12)	0.1180 (13)	0.046 (3)	0.397 (3)
H3B	0.407632	0.485456	0.150607	0.069*	0.397 (3)
H3D	0.49048	0.364985	0.120154	0.069*	0.397 (3)
H3F	0.524597	0.423929	0.034863	0.069*	0.397 (3)
O1B	0.6716 (4)	0.7142 (2)	0.2214 (2)	0.0374 (7)	0.397 (3)
C2	0.72780 (18)	0.52154 (10)	0.19228 (10)	0.0282 (3)
H2	0.821892	0.462556	0.163793	0.034*
C4	0.67093 (19)	0.47360 (11)	0.36251 (10)	0.0301 (3)
H4A	0.538371	0.413432	0.314275	0.036*
H4B	0.646632	0.514876	0.447621	0.036*
C5	0.84137 (19)	0.40507 (10)	0.34979 (9)	0.0276 (2)
H5A	0.981423	0.463282	0.379238	0.033*
H5B	0.820648	0.363371	0.397974	0.033*
C6	0.99162 (17)	0.25555 (10)	0.19395 (10)	0.0239 (2)
C7	1.01307 (17)	0.19803 (10)	0.07140 (10)	0.0232 (2)
C8	1.17644 (18)	0.13710 (10)	0.03294 (10)	0.0254 (2)
C9	1.31082 (18)	0.13268 (11)	0.11611 (11)	0.0293 (3)
H9	1.422881	0.09223	0.090152	0.035*
C10	1.28249 (19)	0.18663 (11)	0.23597 (11)	0.0301 (3)
H10	1.373047	0.181061	0.291163	0.036*
C11	1.12319 (18)	0.24874 (10)	0.27633 (10)	0.0274 (2)
H11	1.104107	0.285988	0.358703	0.033*
C12	0.86223 (19)	0.20306 (11)	−0.01589 (10)	0.0283 (3)
H12A	0.827002	0.123391	−0.090346	0.042*
H12B	0.928362	0.267368	−0.033571	0.042*
H12C	0.733303	0.221702	0.01951	0.042*
C13	1.2099 (2)	0.07789 (11)	−0.09733 (11)	0.0308 (3)
H13A	1.334484	0.043316	−0.107477	0.046*
H13B	1.231059	0.139794	−0.122728	0.046*
H13C	1.085776	0.012067	−0.14644	0.046*
C14	0.26384 (18)	0.71435 (10)	0.44225 (9)	0.0244 (2)
C15	0.44130 (17)	0.82847 (10)	0.51361 (9)	0.0231 (2)
C16	0.40433 (17)	0.93583 (10)	0.60737 (9)	0.0249 (2)
H16	0.266281	0.939552	0.628616	0.03*
C17	0.57110 (18)	1.03717 (10)	0.66934 (10)	0.0273 (2)
H17	0.549518	1.11174	0.733425	0.033*
C18	0.77024 (19)	1.02785 (11)	0.63618 (10)	0.0285 (2)
H18	0.888078	1.095814	0.676964	0.034*
C19	0.79363 (18)	0.91738 (11)	0.54238 (11)	0.0305 (3)
H19	0.930684	0.91115	0.520362	0.037*
N1	0.71983 (16)	0.56730 (9)	0.32404 (8)	0.0269 (2)
N2	0.63362 (15)	0.81869 (9)	0.48087 (8)	0.0285 (2)
O2	0.83080 (12)	0.31628 (7)	0.22573 (7)	0.02673 (19)
O3	0.31104 (14)	0.61537 (7)	0.37268 (8)	0.0350 (2)
O4	0.08058 (12)	0.72907 (7)	0.46149 (7)	0.0308 (2)
H1AO	0.333 (5)	0.556 (3)	0.210 (2)	0.073 (10)*	0.603 (3)
H1BO	0.665 (7)	0.747 (4)	0.2980 (19)	0.057 (13)*	0.397 (3)
H1AN	0.853 (3)	0.6217 (15)	0.3670 (14)	0.044 (4)*
H1BN	0.623 (3)	0.6151 (15)	0.3513 (14)	0.045 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.028 (2)	0.029 (2)	0.022 (2)	−0.0081 (19)	−0.0024 (18)	0.0058 (17)
C3A	0.042 (3)	0.032 (3)	0.060 (4)	0.000 (2)	−0.002 (3)	0.033 (3)
O1A	0.0393 (9)	0.0693 (12)	0.0337 (9)	0.0225 (8)	0.0050 (7)	0.0232 (8)
C1B	0.037 (5)	0.041 (5)	0.020 (3)	0.006 (3)	0.005 (3)	0.005 (3)
C3B	0.057 (6)	0.046 (4)	0.038 (5)	0.022 (4)	0.008 (4)	0.019 (4)
O1B	0.0588 (16)	0.0293 (12)	0.0316 (13)	0.0185 (11)	0.0117 (11)	0.0178 (10)
C2	0.0296 (6)	0.0253 (6)	0.0266 (6)	0.0065 (5)	0.0063 (5)	0.0104 (5)
C4	0.0293 (6)	0.0312 (6)	0.0249 (5)	0.0051 (5)	0.0095 (5)	0.0106 (5)
C5	0.0349 (6)	0.0259 (5)	0.0194 (5)	0.0055 (5)	0.0048 (4)	0.0097 (4)
C6	0.0236 (5)	0.0209 (5)	0.0249 (5)	0.0023 (4)	0.0022 (4)	0.0106 (4)
C7	0.0233 (5)	0.0205 (5)	0.0243 (5)	0.0016 (4)	0.0019 (4)	0.0113 (4)
C8	0.0249 (6)	0.0212 (5)	0.0285 (6)	0.0020 (4)	0.0044 (4)	0.0124 (4)
C9	0.0248 (6)	0.0260 (6)	0.0374 (6)	0.0055 (4)	0.0033 (5)	0.0162 (5)
C10	0.0289 (6)	0.0289 (6)	0.0330 (6)	0.0029 (5)	−0.0045 (5)	0.0175 (5)
C11	0.0302 (6)	0.0248 (5)	0.0234 (5)	0.0018 (5)	−0.0011 (4)	0.0110 (4)
C12	0.0318 (6)	0.0300 (6)	0.0225 (5)	0.0087 (5)	0.0031 (4)	0.0123 (5)
C13	0.0322 (6)	0.0295 (6)	0.0315 (6)	0.0086 (5)	0.0101 (5)	0.0150 (5)
C14	0.0273 (6)	0.0266 (5)	0.0218 (5)	0.0087 (4)	0.0037 (4)	0.0130 (4)
C15	0.0242 (5)	0.0272 (5)	0.0211 (5)	0.0100 (4)	0.0033 (4)	0.0132 (4)
C16	0.0244 (5)	0.0300 (6)	0.0224 (5)	0.0101 (4)	0.0045 (4)	0.0133 (5)
C17	0.0317 (6)	0.0267 (6)	0.0226 (5)	0.0105 (5)	0.0039 (4)	0.0101 (4)
C18	0.0276 (6)	0.0282 (6)	0.0284 (6)	0.0039 (5)	0.0008 (4)	0.0141 (5)
C19	0.0231 (6)	0.0352 (6)	0.0327 (6)	0.0093 (5)	0.0052 (5)	0.0155 (5)
N1	0.0239 (5)	0.0239 (5)	0.0261 (5)	0.0080 (4)	0.0029 (4)	0.0064 (4)
N2	0.0255 (5)	0.0304 (5)	0.0276 (5)	0.0110 (4)	0.0049 (4)	0.0113 (4)
O2	0.0265 (4)	0.0274 (4)	0.0210 (4)	0.0075 (3)	0.0018 (3)	0.0076 (3)
O3	0.0337 (5)	0.0251 (4)	0.0385 (5)	0.0083 (4)	0.0098 (4)	0.0092 (4)
O4	0.0233 (4)	0.0292 (4)	0.0345 (4)	0.0071 (3)	0.0007 (3)	0.0114 (4)

Geometric parameters (Å, º) top

C1A—O1A	1.440 (7)	C7—C8	1.3990 (15)
C1A—C2	1.535 (4)	C7—C12	1.5078 (15)
C1A—H1A	0.99	C8—C9	1.3955 (17)
C1A—H1C	0.99	C8—C13	1.5079 (15)
C3A—C2	1.533 (4)	C9—C10	1.3834 (17)
C3A—H3A	0.98	C9—H9	0.95
C3A—H3C	0.98	C10—C11	1.3864 (17)
C3A—H3E	0.98	C10—H10	0.95
O1A—H1AO	0.877 (18)	C11—H11	0.95
C1B—O1B	1.411 (8)	C12—H12A	0.98
C1B—C2	1.498 (7)	C12—H12B	0.98
C1B—H1B	0.99	C12—H12C	0.98
C1B—H1D	0.99	C13—H13A	0.98
C3B—C2	1.502 (8)	C13—H13B	0.98
C3B—H3B	0.98	C13—H13C	0.98
C3B—H3D	0.98	C14—O3	1.2492 (13)
C3B—H3F	0.98	C14—O4	1.2571 (13)
O1B—H1BO	0.868 (19)	C14—C15	1.5203 (16)
C2—N1	1.5052 (14)	C15—N2	1.3414 (14)
C2—H2	1	C15—C16	1.3896 (15)
C4—N1	1.4867 (15)	C16—C17	1.3826 (17)
C4—C5	1.5082 (16)	C16—H16	0.95
C4—H4A	0.99	C17—C18	1.3850 (16)
C4—H4B	0.99	C17—H17	0.95
C5—O2	1.4300 (13)	C18—C19	1.3825 (17)
C5—H5A	0.99	C18—H18	0.95
C5—H5B	0.99	C19—N2	1.3389 (16)
C6—O2	1.3769 (13)	C19—H19	0.95
C6—C11	1.3931 (16)	N1—H1AN	0.958 (18)
C6—C7	1.4023 (15)	N1—H1BN	0.919 (17)

O1A—C1A—C2	113.6 (4)	C6—C7—C12	119.99 (10)
O1A—C1A—H1A	108.8	C9—C8—C7	119.68 (10)
C2—C1A—H1A	108.8	C9—C8—C13	119.92 (10)
O1A—C1A—H1C	108.8	C7—C8—C13	120.39 (10)
C2—C1A—H1C	108.8	C10—C9—C8	120.66 (11)
H1A—C1A—H1C	107.7	C10—C9—H9	119.7
C2—C3A—H3A	109.5	C8—C9—H9	119.7
C2—C3A—H3C	109.5	C9—C10—C11	120.63 (10)
H3A—C3A—H3C	109.5	C9—C10—H10	119.7
C2—C3A—H3E	109.5	C11—C10—H10	119.7
H3A—C3A—H3E	109.5	C10—C11—C6	118.82 (10)
H3C—C3A—H3E	109.5	C10—C11—H11	120.6
C1A—O1A—H1AO	106 (2)	C6—C11—H11	120.6
O1B—C1B—C2	111.7 (6)	C7—C12—H12A	109.5
O1B—C1B—H1B	109.3	C7—C12—H12B	109.5
C2—C1B—H1B	109.3	H12A—C12—H12B	109.5
O1B—C1B—H1D	109.3	C7—C12—H12C	109.5
C2—C1B—H1D	109.3	H12A—C12—H12C	109.5
H1B—C1B—H1D	108	H12B—C12—H12C	109.5
C2—C3B—H3B	109.5	C8—C13—H13A	109.5
C2—C3B—H3D	109.5	C8—C13—H13B	109.5
H3B—C3B—H3D	109.5	H13A—C13—H13B	109.5
C2—C3B—H3F	109.5	C8—C13—H13C	109.5
H3B—C3B—H3F	109.5	H13A—C13—H13C	109.5
H3D—C3B—H3F	109.5	H13B—C13—H13C	109.5
C1B—O1B—H1BO	113 (3)	O3—C14—O4	125.99 (11)
C3B—C2—N1	111.8 (6)	O3—C14—C15	118.32 (10)
C3B—C2—C1B	115.5 (7)	O4—C14—C15	115.67 (9)
N1—C2—C1B	105.7 (4)	N2—C15—C16	122.54 (10)
N1—C2—C3A	109.5 (3)	N2—C15—C14	116.07 (9)
N1—C2—C1A	111.2 (3)	C16—C15—C14	121.38 (10)
C3A—C2—C1A	111.3 (4)	C17—C16—C15	119.13 (10)
N1—C2—H2	108.3	C17—C16—H16	120.4
C3A—C2—H2	108.3	C15—C16—H16	120.4
C1A—C2—H2	108.3	C16—C17—C18	118.71 (10)
N1—C4—C5	114.13 (9)	C16—C17—H17	120.6
N1—C4—H4A	108.7	C18—C17—H17	120.6
C5—C4—H4A	108.7	C19—C18—C17	118.48 (11)
N1—C4—H4B	108.7	C19—C18—H18	120.8
C5—C4—H4B	108.7	C17—C18—H18	120.8
H4A—C4—H4B	107.6	N2—C19—C18	123.57 (11)
O2—C5—C4	108.47 (9)	N2—C19—H19	118.2
O2—C5—H5A	110	C18—C19—H19	118.2
C4—C5—H5A	110	C4—N1—C2	117.41 (9)
O2—C5—H5B	110	C4—N1—H1AN	108.2 (9)
C4—C5—H5B	110	C2—N1—H1AN	108.0 (9)
H5A—C5—H5B	108.4	C4—N1—H1BN	107.0 (10)
O2—C6—C11	123.01 (10)	C2—N1—H1BN	110.5 (10)
O2—C6—C7	115.50 (9)	H1AN—N1—H1BN	105.1 (13)
C11—C6—C7	121.47 (10)	C19—N2—C15	117.57 (10)
C8—C7—C6	118.68 (10)	C6—O2—C5	116.94 (8)
C8—C7—C12	121.33 (10)

O1B—C1B—C2—C3B	61.6 (11)	O4—C14—C15—N2	−170.18 (9)
O1B—C1B—C2—N1	−62.7 (8)	O3—C14—C15—C16	−168.55 (10)
O1A—C1A—C2—N1	71.1 (6)	O4—C14—C15—C16	10.09 (15)
O1A—C1A—C2—C3A	−51.3 (7)	N2—C15—C16—C17	0.39 (17)
N1—C4—C5—O2	−76.44 (12)	C14—C15—C16—C17	−179.90 (9)
O2—C6—C7—C8	178.45 (9)	C15—C16—C17—C18	−0.42 (16)
C11—C6—C7—C8	−2.70 (16)	C16—C17—C18—C19	−0.01 (17)
O2—C6—C7—C12	−1.31 (15)	C17—C18—C19—N2	0.53 (18)
C11—C6—C7—C12	177.54 (10)	C5—C4—N1—C2	68.07 (13)
C6—C7—C8—C9	1.29 (16)	C3B—C2—N1—C4	61.4 (6)
C12—C7—C8—C9	−178.95 (10)	C1B—C2—N1—C4	−172.1 (4)
C6—C7—C8—C13	−177.84 (10)	C3A—C2—N1—C4	−168.5 (3)
C12—C7—C8—C13	1.92 (16)	C1A—C2—N1—C4	68.1 (3)
C7—C8—C9—C10	0.82 (17)	C18—C19—N2—C15	−0.56 (17)
C13—C8—C9—C10	179.94 (10)	C16—C15—N2—C19	0.09 (16)
C8—C9—C10—C11	−1.59 (17)	C14—C15—N2—C19	−179.63 (10)
C9—C10—C11—C6	0.20 (17)	C11—C6—O2—C5	19.38 (15)
O2—C6—C11—C10	−179.28 (10)	C7—C6—O2—C5	−161.79 (9)
C7—C6—C11—C10	1.96 (16)	C4—C5—O2—C6	171.72 (9)
O3—C14—C15—N2	11.18 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1AN···O4ⁱ	0.96 (2)	1.75 (2)	2.707 (1)	173 (1)
N1—H1BN···N2	0.920 (2)	2.30 (2)	3.028 (1)	136 (1)
N1—H1BN···O3	0.920 (2)	2.06 (2)	2.866 (1)	146 (1)
O1A—H1AO···O3	0.88 (2)	1.87 (2)	2.736 (2)	170 (3)
O1B—H1BO···N2	0.87 (2)	2.10 (2)	2.967 (2)	177 (4)
C2—H2···O2	1	2.37	3.0443 (14)	124
C3A—H3C···O1Aⁱⁱ	0.98	2.66	3.549 (9)	150
C5—H5A···O3ⁱ	0.99	2.64	3.564 (2)	156
C19—H19···O4ⁱ	0.95	2.48	3.127 (1)	125

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z.

(S)-N-[2-(2,6-Dimethylphenoxy)ethyl]-1-hydroxypropan-2-aminium chloride (2c) top

Crystal data top

C₁₃H₂₂NO₂⁺·Cl⁻	F(000) = 280
M_r = 259.76	D_x = 1.269 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 13959 reflections
a = 7.0226 (1) Å	θ = 3.6–77.3°
b = 7.9585 (1) Å	µ = 2.41 mm⁻¹
c = 12.5188 (1) Å	T = 100 K
β = 103.645 (1)°	Irregular, clear colourless
V = 679.92 (1) Å³	0.24 × 0.18 × 0.12 mm
Z = 2

Data collection top

Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector	2786 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2771 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.031
Detector resolution: 10 pixels mm^-1	θ_max = 77.3°, θ_min = 3.6°
ω scans	h = −8→8
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2019)	k = −10→10
T_min = 0.41, T_max = 1	l = −15→14
15929 measured reflections

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0342P)² + 0.1124P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.022	(Δ/σ)_max < 0.001
wR(F²) = 0.058	Δρ_max = 0.27 e Å⁻³
S = 1.07	Δρ_min = −0.16 e Å⁻³
2786 reflections	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
170 parameters	Extinction coefficient: 0.0150 (12)
1 restraint	Absolute structure: Flack x determined using 1247 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: mixed	Absolute structure parameter: −0.015 (6)

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.3756 (3)	0.3606 (2)	0.55251 (15)	0.0209 (4)
H1A	0.375431	0.390983	0.629173	0.025*
H1B	0.329735	0.243	0.539851	0.025*
C2	0.2374 (3)	0.4769 (2)	0.47322 (14)	0.0163 (4)
H13	0.268072	0.596059	0.496292	0.02*
C3	0.0229 (3)	0.4423 (3)	0.46877 (16)	0.0229 (4)
H3A	−0.059321	0.518021	0.415443	0.034*
H3B	−0.002288	0.461033	0.541576	0.034*
H3C	−0.008017	0.325531	0.446418	0.034*
C4	0.2040 (2)	0.5770 (3)	0.27671 (12)	0.0146 (3)
H4A	0.221796	0.691228	0.308802	0.017*
H4B	0.06226	0.558154	0.246011	0.017*
C5	0.3142 (2)	0.5605 (2)	0.18722 (13)	0.0158 (3)
H5A	0.29165	0.448179	0.152517	0.019*
H5B	0.269534	0.646878	0.129893	0.019*
C6	0.6373 (2)	0.5403 (2)	0.16658 (14)	0.0140 (4)
C7	0.7014 (2)	0.3737 (2)	0.16595 (14)	0.0147 (3)
C8	0.8127 (2)	0.3313 (2)	0.09093 (14)	0.0162 (3)
H8	0.86019	0.219817	0.089374	0.019*
C9	0.8547 (3)	0.4505 (2)	0.01851 (14)	0.0164 (3)
H9	0.924947	0.418889	−0.034544	0.02*
C10	0.7938 (2)	0.6157 (2)	0.02381 (14)	0.0158 (4)
H10	0.824855	0.696656	−0.025223	0.019*
C11	0.6879 (2)	0.6648 (2)	0.09997 (15)	0.0149 (3)
C12	0.6528 (3)	0.2446 (2)	0.24365 (15)	0.0178 (4)
H12A	0.651897	0.298171	0.314001	0.027*
H12B	0.751649	0.155223	0.255604	0.027*
H12C	0.523467	0.196388	0.21184	0.027*
C13	0.6403 (3)	0.8472 (2)	0.11285 (15)	0.0185 (4)
H13A	0.529811	0.855627	0.147979	0.028*
H13B	0.60521	0.900709	0.040353	0.028*
H13C	0.754755	0.903803	0.15859	0.028*
Cl1	0.17264 (5)	0.08253 (5)	0.28280 (3)	0.01826 (12)
N1	0.2823 (2)	0.44921 (19)	0.36289 (12)	0.0145 (3)
O1	0.56934 (19)	0.37453 (18)	0.53653 (11)	0.0225 (3)
O2	0.51912 (15)	0.58314 (18)	0.23836 (8)	0.0141 (2)
H1O	0.637 (4)	0.437 (4)	0.583 (3)	0.045 (8)*
H1AN	0.248 (3)	0.341 (4)	0.3404 (19)	0.024 (6)*
H2BN	0.409 (4)	0.451 (3)	0.372 (2)	0.028 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0242 (9)	0.0219 (9)	0.0162 (8)	−0.0004 (7)	0.0043 (7)	0.0022 (7)
C2	0.0200 (9)	0.0175 (8)	0.0130 (8)	−0.0004 (7)	0.0068 (6)	−0.0012 (7)
C3	0.0206 (9)	0.0289 (10)	0.0220 (9)	−0.0010 (8)	0.0107 (7)	−0.0015 (8)
C4	0.0139 (7)	0.0156 (7)	0.0144 (7)	0.0013 (8)	0.0039 (5)	0.0014 (8)
C5	0.0129 (7)	0.0198 (9)	0.0143 (7)	−0.0002 (7)	0.0022 (6)	−0.0005 (7)
C6	0.0120 (7)	0.0174 (9)	0.0126 (8)	−0.0004 (6)	0.0028 (6)	−0.0017 (6)
C7	0.0137 (7)	0.0151 (8)	0.0147 (8)	−0.0019 (6)	0.0025 (6)	−0.0002 (7)
C8	0.0149 (7)	0.0144 (8)	0.0193 (8)	0.0008 (6)	0.0041 (6)	−0.0022 (7)
C9	0.0142 (8)	0.0209 (9)	0.0149 (8)	−0.0009 (6)	0.0049 (6)	−0.0025 (7)
C10	0.0152 (8)	0.0174 (10)	0.0150 (8)	−0.0028 (6)	0.0041 (6)	0.0025 (6)
C11	0.0130 (7)	0.0161 (8)	0.0145 (8)	−0.0010 (7)	0.0011 (6)	0.0003 (7)
C12	0.0176 (8)	0.0156 (8)	0.0215 (9)	0.0003 (6)	0.0073 (6)	0.0024 (7)
C13	0.0213 (8)	0.0142 (8)	0.0204 (8)	−0.0003 (7)	0.0059 (7)	0.0016 (7)
Cl1	0.01893 (19)	0.01711 (19)	0.0189 (2)	0.00029 (16)	0.00483 (13)	0.00074 (17)
N1	0.0149 (7)	0.0151 (7)	0.0145 (7)	0.0010 (6)	0.0057 (5)	−0.0004 (6)
O1	0.0200 (6)	0.0256 (7)	0.0200 (6)	0.0021 (5)	0.0006 (5)	−0.0030 (5)
O2	0.0123 (5)	0.0173 (5)	0.0131 (5)	0.0000 (5)	0.0040 (4)	−0.0022 (6)

Geometric parameters (Å, º) top

C1—O1	1.426 (2)	C6—O2	1.401 (2)
C1—C2	1.526 (2)	C7—C8	1.398 (2)
C1—H1A	0.99	C7—C12	1.508 (2)
C1—H1B	0.99	C8—C9	1.391 (3)
C2—N1	1.504 (2)	C8—H8	0.95
C2—C3	1.519 (2)	C9—C10	1.389 (3)
C2—H13	1	C9—H9	0.95
C3—H3A	0.98	C10—C11	1.397 (3)
C3—H3B	0.98	C10—H10	0.95
C3—H3C	0.98	C11—C13	1.506 (2)
C4—N1	1.490 (2)	C12—H12A	0.98
C4—C5	1.510 (2)	C12—H12B	0.98
C4—H4A	0.99	C12—H12C	0.98
C4—H4B	0.99	C13—H13A	0.98
C5—O2	1.4419 (18)	C13—H13B	0.98
C5—H5A	0.99	C13—H13C	0.98
C5—H5B	0.99	N1—H1AN	0.92 (3)
C6—C11	1.394 (2)	N1—H2BN	0.87 (3)
C6—C7	1.401 (2)	O1—H1O	0.83 (3)

O1—C1—C2	110.06 (15)	C8—C7—C12	121.08 (16)
O1—C1—H1A	109.6	C6—C7—C12	121.30 (15)
C2—C1—H1A	109.6	C9—C8—C7	120.78 (17)
O1—C1—H1B	109.6	C9—C8—H8	119.6
C2—C1—H1B	109.6	C7—C8—H8	119.6
H1A—C1—H1B	108.2	C10—C9—C8	119.96 (16)
N1—C2—C3	111.14 (14)	C10—C9—H9	120
N1—C2—C1	105.64 (14)	C8—C9—H9	120
C3—C2—C1	112.75 (16)	C9—C10—C11	121.14 (16)
N1—C2—H13	109.1	C9—C10—H10	119.4
C3—C2—H13	109.1	C11—C10—H10	119.4
C1—C2—H13	109.1	C6—C11—C10	117.47 (15)
C2—C3—H3A	109.5	C6—C11—C13	121.77 (16)
C2—C3—H3B	109.5	C10—C11—C13	120.69 (16)
H3A—C3—H3B	109.5	C7—C12—H12A	109.5
C2—C3—H3C	109.5	C7—C12—H12B	109.5
H3A—C3—H3C	109.5	H12A—C12—H12B	109.5
H3B—C3—H3C	109.5	C7—C12—H12C	109.5
N1—C4—C5	108.16 (14)	H12A—C12—H12C	109.5
N1—C4—H4A	110.1	H12B—C12—H12C	109.5
C5—C4—H4A	110.1	C11—C13—H13A	109.5
N1—C4—H4B	110.1	C11—C13—H13B	109.5
C5—C4—H4B	110.1	H13A—C13—H13B	109.5
H4A—C4—H4B	108.4	C11—C13—H13C	109.5
O2—C5—C4	107.00 (12)	H13A—C13—H13C	109.5
O2—C5—H5A	110.3	H13B—C13—H13C	109.5
C4—C5—H5A	110.3	C4—N1—C2	116.34 (14)
O2—C5—H5B	110.3	C4—N1—H1AN	113.0 (15)
C4—C5—H5B	110.3	C2—N1—H1AN	108.8 (15)
H5A—C5—H5B	108.6	C4—N1—H2BN	105.5 (17)
C11—C6—C7	122.81 (16)	C2—N1—H2BN	108.2 (16)
C11—C6—O2	118.92 (15)	H1AN—N1—H2BN	104 (2)
C7—C6—O2	118.26 (15)	C1—O1—H1O	111 (2)
C8—C7—C6	117.62 (16)	C6—O2—C5	111.39 (12)

O1—C1—C2—N1	46.40 (19)	O2—C6—C11—C10	−175.51 (14)
O1—C1—C2—C3	167.97 (15)	C7—C6—C11—C13	−171.59 (17)
N1—C4—C5—O2	−57.64 (19)	O2—C6—C11—C13	7.6 (2)
C11—C6—C7—C8	−3.2 (2)	C9—C10—C11—C6	−3.1 (2)
O2—C6—C7—C8	177.55 (14)	C9—C10—C11—C13	173.78 (15)
C11—C6—C7—C12	176.58 (15)	C5—C4—N1—C2	162.26 (15)
O2—C6—C7—C12	−2.7 (2)	C3—C2—N1—C4	72.16 (19)
C6—C7—C8—C9	−1.1 (2)	C1—C2—N1—C4	−165.24 (14)
C12—C7—C8—C9	179.14 (16)	C11—C6—O2—C5	91.09 (18)
C7—C8—C9—C10	3.1 (3)	C7—C6—O2—C5	−89.64 (18)
C8—C9—C10—C11	−0.9 (3)	C4—C5—O2—C6	169.26 (15)
C7—C6—C11—C10	5.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1AN···Cl1	0.92 (3)	2.21 (3)	3.122 (2)	178 (2)
N1—H2BN···O2	0.87 (3)	2.25 (3)	2.749 (2)	116 (2)
N1—H2BN···O1	0.87 (3)	2.19 (2)	2.660 (2)	113 (2)
O1—H1O···Cl1ⁱ	0.83 (3)	2.21 (3)	3.034 (2)	174 (3)
C2—H13···O1ⁱ	1	2.57	3.457 (2)	148
C3—H3B···Cl1ⁱⁱ	0.98	2.91	3.850 (2)	162
C4—H4A···O1ⁱ	0.99	2.59	3.443 (2)	145

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x, y+1/2, −z+1.

(R,S)-N-[2-(2,6-Dimethylphenoxy)ethyl]-1-hydroxypropan-2-aminium pyridine-2-carboxylate (2p) top

Crystal data top

C₁₃H₂₂NO₂⁺·C₆H₄NO₂⁻	D_x = 1.199 Mg m⁻³
M_r = 346.42	Cu Kα radiation, λ = 1.54184 Å
Tetragonal, P4₁2₁2	Cell parameters from 7917 reflections
Hall symbol: P 4abw 2nw	θ = 4.3–70.4°
a = 10.9828 (1) Å	µ = 0.69 mm⁻¹
c = 31.8240 (4) Å	T = 130 K
V = 3838.67 (8) Å³	Irregular, colourless
Z = 8	0.62 × 0.42 × 0.37 mm
F(000) = 1488

Data collection top

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	3670 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	3428 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.032
Detector resolution: 10.3756 pixels mm^-1	θ_max = 70.6°, θ_min = 4.3°
ω scans	h = −13→10
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	k = −7→13
T_min = 0.383, T_max = 1	l = −38→38
15589 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)] = 0.031	w = 1/[σ²(F_o²) + (0.0474P)² + 0.2711P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.081	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.14 e Å⁻³
3670 reflections	Δρ_min = −0.16 e Å⁻³
241 parameters	Absolute structure: Flack x determined using 1323 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.06 (9)

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.77163 (18)	0.30120 (18)	0.15168 (5)	0.0355 (4)
H1A	0.816934	0.319715	0.1778	0.043*
H1B	0.818427	0.238986	0.135991	0.043*
C2	0.64789 (17)	0.24857 (16)	0.16325 (5)	0.0300 (4)
H2	0.604533	0.224027	0.136951	0.036*
C3	0.6622 (2)	0.13774 (19)	0.19127 (6)	0.0457 (5)
H3A	0.703709	0.161261	0.217292	0.069*
H3B	0.710376	0.075795	0.176628	0.069*
H3C	0.581661	0.104583	0.198002	0.069*
C4	0.49464 (17)	0.41897 (17)	0.15865 (5)	0.0321 (4)
H4A	0.43632	0.366963	0.143141	0.039*
H4B	0.546008	0.462122	0.137872	0.039*
C5	0.42539 (18)	0.51111 (17)	0.18514 (5)	0.0342 (4)
H5A	0.362947	0.470197	0.20258	0.041*
H5B	0.481544	0.556378	0.203802	0.041*
C6	0.28704 (17)	0.67296 (17)	0.17269 (5)	0.0315 (4)
C7	0.32882 (18)	0.78580 (18)	0.18622 (6)	0.0360 (4)
C8	0.2425 (2)	0.87075 (18)	0.19884 (6)	0.0397 (4)
H8	0.268129	0.948956	0.208036	0.048*
C9	0.11950 (19)	0.84275 (18)	0.19819 (6)	0.0386 (4)
H9	0.061474	0.902446	0.206284	0.046*
C10	0.08063 (18)	0.72830 (18)	0.18581 (5)	0.0342 (4)
H10	−0.003733	0.709242	0.186186	0.041*
C11	0.16410 (18)	0.64140 (17)	0.17287 (5)	0.0325 (4)
C12	0.4623 (2)	0.8174 (2)	0.18646 (8)	0.0534 (6)
H12A	0.471915	0.905879	0.188575	0.08*
H12B	0.50011	0.788508	0.160409	0.08*
H12C	0.501757	0.778285	0.210569	0.08*
C13	0.1222 (2)	0.5180 (2)	0.15811 (8)	0.0506 (5)
H13A	0.14093	0.456939	0.179625	0.076*
H13B	0.164205	0.496893	0.131937	0.076*
H13C	0.034117	0.51977	0.153172	0.076*
C14	0.40791 (16)	0.24656 (15)	0.28451 (5)	0.0273 (4)
C15	0.30159 (16)	0.22413 (15)	0.25487 (5)	0.0274 (3)
C16	0.18458 (17)	0.20824 (17)	0.27018 (5)	0.0329 (4)
H16	0.168711	0.211017	0.299513	0.039*
C17	0.09115 (18)	0.18817 (18)	0.24170 (6)	0.0386 (4)
H17	0.010006	0.176838	0.251264	0.046*
C18	0.11727 (19)	0.18486 (18)	0.19941 (6)	0.0384 (4)
H18	0.05497	0.170676	0.179285	0.046*
C19	0.23646 (19)	0.20270 (18)	0.18700 (5)	0.0371 (4)
H19	0.254202	0.20044	0.157799	0.045*
N1	0.57243 (14)	0.34204 (13)	0.18605 (4)	0.0259 (3)
N2	0.32857 (14)	0.22303 (14)	0.21373 (4)	0.0311 (3)
O1	0.76427 (14)	0.40788 (13)	0.12711 (4)	0.0402 (3)
O2	0.37010 (13)	0.59073 (13)	0.15550 (4)	0.0375 (3)
O3	0.50471 (11)	0.28574 (13)	0.26799 (3)	0.0333 (3)
O4	0.39189 (12)	0.22549 (14)	0.32255 (4)	0.0383 (3)
H1O	0.766 (3)	0.470 (3)	0.1460 (9)	0.070 (8)*
H1AN	0.524 (2)	0.307 (2)	0.2047 (7)	0.043 (6)*
H1BN	0.625 (2)	0.392 (2)	0.2014 (7)	0.047 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0361 (10)	0.0389 (10)	0.0313 (8)	0.0051 (8)	0.0052 (7)	−0.0051 (7)
C2	0.0385 (9)	0.0265 (9)	0.0250 (7)	0.0047 (7)	0.0006 (7)	−0.0038 (6)
C3	0.0663 (15)	0.0302 (10)	0.0407 (10)	0.0111 (10)	0.0076 (10)	0.0005 (8)
C4	0.0338 (9)	0.0362 (10)	0.0264 (7)	0.0067 (8)	−0.0021 (7)	0.0013 (7)
C5	0.0387 (10)	0.0353 (10)	0.0287 (8)	0.0062 (8)	−0.0026 (7)	0.0031 (7)
C6	0.0364 (10)	0.0326 (9)	0.0254 (7)	0.0057 (8)	0.0004 (7)	0.0035 (6)
C7	0.0376 (10)	0.0348 (10)	0.0357 (9)	−0.0019 (8)	−0.0005 (7)	0.0072 (8)
C8	0.0509 (12)	0.0274 (9)	0.0408 (10)	−0.0007 (9)	−0.0013 (8)	−0.0009 (7)
C9	0.0451 (11)	0.0350 (10)	0.0357 (9)	0.0095 (9)	0.0011 (8)	0.0002 (7)
C10	0.0335 (9)	0.0410 (10)	0.0281 (8)	0.0020 (8)	0.0012 (7)	0.0037 (7)
C11	0.0381 (10)	0.0316 (9)	0.0278 (8)	0.0010 (8)	−0.0018 (7)	0.0000 (7)
C12	0.0417 (12)	0.0441 (12)	0.0745 (15)	−0.0073 (10)	−0.0014 (11)	0.0048 (11)
C13	0.0462 (13)	0.0394 (12)	0.0660 (14)	−0.0022 (10)	−0.0032 (11)	−0.0105 (10)
C14	0.0292 (9)	0.0276 (9)	0.0251 (7)	−0.0015 (7)	−0.0004 (6)	−0.0019 (6)
C15	0.0305 (9)	0.0233 (8)	0.0285 (7)	−0.0010 (7)	−0.0019 (7)	−0.0014 (6)
C16	0.0339 (10)	0.0319 (9)	0.0329 (8)	0.0007 (8)	0.0005 (7)	−0.0033 (7)
C17	0.0283 (9)	0.0374 (10)	0.0501 (11)	0.0018 (8)	−0.0022 (8)	−0.0050 (8)
C18	0.0371 (10)	0.0336 (10)	0.0445 (10)	0.0021 (8)	−0.0139 (8)	−0.0062 (8)
C19	0.0450 (11)	0.0366 (10)	0.0299 (8)	−0.0014 (9)	−0.0063 (7)	−0.0037 (7)
N1	0.0300 (8)	0.0256 (7)	0.0220 (6)	0.0012 (6)	0.0013 (6)	−0.0002 (6)
N2	0.0349 (8)	0.0321 (8)	0.0263 (7)	−0.0018 (7)	−0.0022 (6)	−0.0019 (6)
O1	0.0511 (9)	0.0397 (7)	0.0297 (6)	−0.0063 (7)	0.0097 (6)	−0.0030 (5)
O2	0.0422 (8)	0.0408 (7)	0.0293 (6)	0.0142 (6)	0.0013 (5)	0.0043 (5)
O3	0.0313 (7)	0.0436 (7)	0.0249 (5)	−0.0102 (6)	0.0001 (5)	0.0007 (5)
O4	0.0345 (7)	0.0561 (9)	0.0241 (6)	−0.0083 (6)	0.0008 (5)	0.0022 (5)

Geometric parameters (Å, º) top

C1—O1	1.411 (2)	C10—C11	1.386 (3)
C1—C2	1.522 (3)	C10—H10	0.95
C1—H1A	0.99	C11—C13	1.507 (3)
C1—H1B	0.99	C12—H12A	0.98
C2—N1	1.506 (2)	C12—H12B	0.98
C2—C3	1.517 (3)	C12—H12C	0.98
C2—H2	1	C13—H13A	0.98
C3—H3A	0.98	C13—H13B	0.98
C3—H3B	0.98	C13—H13C	0.98
C3—H3C	0.98	C14—O4	1.245 (2)
C4—N1	1.485 (2)	C14—O3	1.262 (2)
C4—C5	1.521 (2)	C14—C15	1.521 (2)
C4—H4A	0.99	C15—N2	1.342 (2)
C4—H4B	0.99	C15—C16	1.386 (2)
C5—O2	1.422 (2)	C16—C17	1.387 (3)
C5—H5A	0.99	C16—H16	0.95
C5—H5B	0.99	C17—C18	1.377 (3)
C6—C7	1.390 (3)	C17—H17	0.95
C6—C11	1.394 (3)	C18—C19	1.381 (3)
C6—O2	1.395 (2)	C18—H18	0.95
C7—C8	1.389 (3)	C19—N2	1.340 (2)
C7—C12	1.507 (3)	C19—H19	0.95
C8—C9	1.386 (3)	N1—H1AN	0.89 (2)
C8—H8	0.95	N1—H1BN	0.94 (3)
C9—C10	1.385 (3)	O1—H1O	0.91 (3)
C9—H9	0.95

O1—C1—C2	113.47 (15)	C11—C10—H10	119.8
O1—C1—H1A	108.9	C10—C11—C6	118.07 (18)
C2—C1—H1A	108.9	C10—C11—C13	120.66 (19)
O1—C1—H1B	108.9	C6—C11—C13	121.23 (17)
C2—C1—H1B	108.9	C7—C12—H12A	109.5
H1A—C1—H1B	107.7	C7—C12—H12B	109.5
N1—C2—C3	108.71 (14)	H12A—C12—H12B	109.5
N1—C2—C1	110.44 (14)	C7—C12—H12C	109.5
C3—C2—C1	110.77 (16)	H12A—C12—H12C	109.5
N1—C2—H2	109	H12B—C12—H12C	109.5
C3—C2—H2	109	C11—C13—H13A	109.5
C1—C2—H2	109	C11—C13—H13B	109.5
C2—C3—H3A	109.5	H13A—C13—H13B	109.5
C2—C3—H3B	109.5	C11—C13—H13C	109.5
H3A—C3—H3B	109.5	H13A—C13—H13C	109.5
C2—C3—H3C	109.5	H13B—C13—H13C	109.5
H3A—C3—H3C	109.5	O4—C14—O3	126.00 (16)
H3B—C3—H3C	109.5	O4—C14—C15	117.67 (15)
N1—C4—C5	109.93 (13)	O3—C14—C15	116.33 (13)
N1—C4—H4A	109.7	N2—C15—C16	123.14 (15)
C5—C4—H4A	109.7	N2—C15—C14	115.90 (15)
N1—C4—H4B	109.7	C16—C15—C14	120.95 (14)
C5—C4—H4B	109.7	C15—C16—C17	118.44 (16)
H4A—C4—H4B	108.2	C15—C16—H16	120.8
O2—C5—C4	104.76 (13)	C17—C16—H16	120.8
O2—C5—H5A	110.8	C18—C17—C16	119.29 (18)
C4—C5—H5A	110.8	C18—C17—H17	120.4
O2—C5—H5B	110.8	C16—C17—H17	120.4
C4—C5—H5B	110.8	C17—C18—C19	118.24 (17)
H5A—C5—H5B	108.9	C17—C18—H18	120.9
C7—C6—C11	122.70 (17)	C19—C18—H18	120.9
C7—C6—O2	118.86 (17)	N2—C19—C18	123.89 (16)
C11—C6—O2	118.28 (17)	N2—C19—H19	118.1
C8—C7—C6	117.58 (18)	C18—C19—H19	118.1
C8—C7—C12	120.52 (19)	C4—N1—C2	114.95 (12)
C6—C7—C12	121.88 (19)	C4—N1—H1AN	107.0 (15)
C9—C8—C7	120.78 (19)	C2—N1—H1AN	110.9 (15)
C9—C8—H8	119.6	C4—N1—H1BN	109.1 (14)
C7—C8—H8	119.6	C2—N1—H1BN	108.2 (15)
C10—C9—C8	120.42 (18)	H1AN—N1—H1BN	106.5 (19)
C10—C9—H9	119.8	C19—N2—C15	116.98 (16)
C8—C9—H9	119.8	C1—O1—H1O	105.0 (18)
C9—C10—C11	120.38 (19)	C6—O2—C5	114.63 (12)
C9—C10—H10	119.8

O1—C1—C2—N1	−56.86 (18)	O3—C14—C15—N2	13.7 (2)
O1—C1—C2—C3	−177.35 (14)	O4—C14—C15—C16	14.5 (3)
N1—C4—C5—O2	171.12 (15)	O3—C14—C15—C16	−165.17 (17)
C11—C6—C7—C8	−2.4 (3)	N2—C15—C16—C17	1.1 (3)
O2—C6—C7—C8	173.02 (15)	C14—C15—C16—C17	179.96 (16)
C11—C6—C7—C12	178.95 (18)	C15—C16—C17—C18	−0.1 (3)
O2—C6—C7—C12	−5.6 (3)	C16—C17—C18—C19	−0.5 (3)
C6—C7—C8—C9	0.5 (3)	C17—C18—C19—N2	0.1 (3)
C12—C7—C8—C9	179.2 (2)	C5—C4—N1—C2	−178.76 (16)
C7—C8—C9—C10	1.5 (3)	C3—C2—N1—C4	−147.72 (17)
C8—C9—C10—C11	−1.7 (3)	C1—C2—N1—C4	90.56 (18)
C9—C10—C11—C6	−0.1 (2)	C18—C19—N2—C15	0.9 (3)
C9—C10—C11—C13	−178.14 (18)	C16—C15—N2—C19	−1.5 (3)
C7—C6—C11—C10	2.2 (2)	C14—C15—N2—C19	179.61 (16)
O2—C6—C11—C10	−173.25 (14)	C7—C6—O2—C5	90.0 (2)
C7—C6—C11—C13	−179.77 (18)	C11—C6—O2—C5	−94.34 (19)
O2—C6—C11—C13	4.8 (2)	C4—C5—O2—C6	171.21 (16)
O4—C14—C15—N2	−166.60 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1AN···N2	0.89 (2)	2.35 (2)	3.108 (2)	143.5 (19)
N1—H1AN···O3	0.89 (2)	2.04 (2)	2.781 (2)	140 (2)
N1—H1BN···O3ⁱ	0.94 (3)	1.78 (3)	2.720 (2)	175 (2)
O1—H1O···O4ⁱ	0.91 (3)	1.82 (3)	2.723 (2)	172 (3)
C3—H3B···O1ⁱⁱ	0.98	2.53	3.430 (2)	153
C4—H4B···O1	0.99	2.49	3.129 (2)	122

Symmetry codes: (i) −y+1, −x+1, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/4.

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The conformational analyses of 2-amino-N-[2-(di­methyl­phen­oxy)eth­yl]­propan-1-ol derivatives in different environments

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The conformational analyses of 2-amino-N-[2-(dimethylphenoxy)ethyl]propan-1-ol derivatives in different environments