Conformational analysis of the salts of N-[(2,3-di­methyl­phen­oxy)alk­yl]amino­alkanol derivatives

Four new crystal structures of the salts of N-[(2,3-di­methyl­phen­oxy)alk­yl]amino­alkanol derivatives with anti­convulsant activity are reported. Bis{D,L-trans-N-[(2,3-di­methyl­phen­oxy)eth­yl]-1-hy­droxy­cyclo­hexan-2-aminium} succinate, 2C₁₆H₂₆NO₂⁺·C₄H₄O₄²⁻, 1, and its polymorph 1p, crystallize in the monoclinic space group P2₁/n, 1 with two cations and one anion, and 1p with four cations and two anions in the asymmetric unit. The other two salts, D,L-trans-N-[(2,3-di­methyl­phen­oxy)eth­yl]-1-hy­droxy­cyclo­hexan-2-aminium 6-carb­oxy­pyridine-2-carboxyl­ate, C₁₆H₂₅NO₂⁺·C₇H₄O₄⁻, 2, and N-[(2,3-di­methyl­phen­oxy)prop­yl]-3-hy­droxy­piperidinium pyridine-2-carboxyl­ate, C₁₆H₂₆NO₂⁺·C₆H₄O₂⁻, 3, crystallize in the monoclinic space group P2₁/c, with one cation and one anion in each asymmetric unit. The geometry of the created polymorphs indicates the main differences in the conformation of the linker between the two rings. The arrangement of the ether O atom and the N atom shows an unusual anti­periplanar conformation for the cations of 1p. The crystal packing of all four salts is dominated by charge-assisted hy­dro­gen bonding between the pro­ton­ated N atom and the carboxyl­ate group of the corresponding acid. Structural studies have been enriched by quantum chemical calculations.

Computing details

Bis{D,L-trans-N-[(2,3-dimethylphenoxy)ethyl]-1-hydroxycyclohexan-2-aminium} succinate (1)

Crystal data

2C16H26NO2^+·C4H4O4^2^−	F(000) = 1400
Mr = 644.82	Dx = 1.256 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 19.0186 (2) Å	Cell parameters from 14530 reflections
b = 7.9125 (1) Å	θ = 3.3–77.4°
c = 22.9406 (3) Å	µ = 0.71 mm^−1
β = 99.068 (1)°	T = 100 K
V = 3409.06 (7) Å^3	Needle, colourless
Z = 4	0.41 × 0.06 × 0.02 mm

Data collection

Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector	12810 measured reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	12810 independent reflections
Mirror monochromator	11876 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	θmax = 77.5°, θmin = 2.8°
ω scans	h = −24→23
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019)	k = −9→9
Tmin = 0.944, Tmax = 1.000	l = −28→28

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0543P)^2 + 1.1923P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
12810 reflections	Δρmax = 0.23 e Å^−3
443 parameters	Δρmin = −0.20 e Å^−3
0 restraints

Special details

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.

Refinement. Refined as a 2-component perfect twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.80041 (7)	−0.30824 (15)	0.47506 (6)	0.0167 (2)
O1A	0.67708 (6)	−0.34405 (14)	0.37590 (5)	0.0213 (2)
O2A	0.74982 (6)	−0.03199 (14)	0.54100 (5)	0.0230 (2)
C1A	0.62429 (8)	−0.27970 (19)	0.33372 (7)	0.0205 (3)
C2A	0.55694 (8)	−0.26807 (19)	0.35107 (7)	0.0216 (3)
C3A	0.50074 (9)	−0.19875 (19)	0.31133 (8)	0.0251 (3)
C4A	0.51239 (9)	−0.1479 (2)	0.25533 (8)	0.0285 (4)
H4A	0.474185	−0.101632	0.228383	0.034*
C5A	0.57867 (10)	−0.1639 (2)	0.23863 (8)	0.0289 (4)
H5A	0.585580	−0.130422	0.200168	0.035*
C6A	0.63541 (9)	−0.2290 (2)	0.27792 (7)	0.0253 (3)
H6A	0.681246	−0.238749	0.266707	0.030*
C7A	0.54756 (9)	−0.3284 (2)	0.41174 (7)	0.0256 (3)
H7AA	0.565184	−0.241934	0.440993	0.038*
H7AB	0.574432	−0.433310	0.420938	0.038*
H7AC	0.496958	−0.349278	0.412690	0.038*
C8A	0.42807 (9)	−0.1743 (2)	0.32883 (9)	0.0337 (4)
H8AA	0.408198	−0.284487	0.337001	0.050*
H8AB	0.396508	−0.118958	0.296547	0.050*
H8AC	0.432374	−0.103604	0.364291	0.050*
C9A	0.74901 (8)	−0.32388 (19)	0.36652 (7)	0.0193 (3)
H9AA	0.760159	−0.202343	0.363319	0.023*
H9AB	0.755991	−0.380312	0.329342	0.023*
C10A	0.79762 (8)	−0.40168 (18)	0.41807 (6)	0.0181 (3)
H10A	0.781629	−0.518811	0.423639	0.022*
H10B	0.846374	−0.407757	0.408163	0.022*
C11A	0.73585 (8)	−0.32160 (18)	0.50531 (7)	0.0181 (3)
H11A	0.693115	−0.284498	0.477086	0.022*
C12A	0.74520 (8)	−0.20336 (18)	0.55880 (7)	0.0190 (3)
H12A	0.789410	−0.234764	0.586324	0.023*
C13A	0.68100 (9)	−0.2208 (2)	0.59042 (7)	0.0235 (3)
H13A	0.637337	−0.188075	0.563340	0.028*
H13B	0.686399	−0.143712	0.624818	0.028*
C14A	0.67369 (9)	−0.4019 (2)	0.61119 (7)	0.0256 (3)
H14A	0.632058	−0.410469	0.632058	0.031*
H14B	0.716711	−0.433662	0.639213	0.031*
C15A	0.66428 (9)	−0.5230 (2)	0.55882 (8)	0.0274 (3)
H15A	0.618435	−0.499092	0.533184	0.033*
H15B	0.662725	−0.640521	0.573327	0.033*
C16A	0.72508 (9)	−0.50561 (19)	0.52273 (7)	0.0240 (3)
H16A	0.714413	−0.575436	0.486606	0.029*
H16B	0.769644	−0.548612	0.546187	0.029*
N1B	1.03621 (7)	0.79844 (16)	0.36652 (6)	0.0168 (2)
O1B	0.93603 (6)	0.83312 (14)	0.25290 (5)	0.0221 (2)
O2B	1.12789 (6)	0.52740 (13)	0.33764 (5)	0.0220 (2)
C1B	0.89033 (8)	0.77390 (19)	0.20450 (7)	0.0211 (3)
C2B	0.92213 (8)	0.74501 (19)	0.15421 (7)	0.0215 (3)
C3B	0.88001 (9)	0.68209 (19)	0.10333 (7)	0.0250 (3)
C4B	0.80783 (9)	0.6504 (2)	0.10369 (8)	0.0288 (4)
H4B	0.779345	0.606743	0.069232	0.035*
C5B	0.77729 (9)	0.6815 (2)	0.15336 (8)	0.0290 (4)
H5B	0.727992	0.660469	0.152694	0.035*
C6B	0.81849 (9)	0.7436 (2)	0.20444 (8)	0.0259 (3)
H6B	0.797692	0.764821	0.238753	0.031*
C7B	1.00049 (9)	0.7794 (2)	0.15749 (7)	0.0241 (3)
H7BA	1.011931	0.889757	0.175966	0.036*
H7BB	1.012766	0.779580	0.117579	0.036*
H7BC	1.027793	0.691234	0.181077	0.036*
C8B	0.91165 (10)	0.6445 (2)	0.04834 (8)	0.0323 (4)
H8BA	0.931463	0.748454	0.034311	0.049*
H8BB	0.874484	0.600476	0.017623	0.049*
H8BC	0.949533	0.560154	0.057396	0.049*
C9B	0.91195 (8)	0.8260 (2)	0.30860 (7)	0.0216 (3)
H9BA	0.902016	0.707313	0.318301	0.026*
H9BB	0.867356	0.891584	0.306929	0.026*
C10B	0.96856 (8)	0.89830 (19)	0.35553 (7)	0.0200 (3)
H10C	0.979800	1.014450	0.343855	0.024*
H10D	0.948964	0.906340	0.392940	0.024*
C11B	1.08571 (8)	0.81797 (18)	0.32199 (6)	0.0167 (3)
H11B	1.059947	0.785202	0.282185	0.020*
C12B	1.14930 (8)	0.69936 (18)	0.33880 (7)	0.0169 (3)
H12B	1.174325	0.728661	0.379196	0.020*
C13B	1.20021 (8)	0.7212 (2)	0.29452 (7)	0.0222 (3)
H13C	1.175539	0.690900	0.254610	0.027*
H13D	1.241143	0.643603	0.304715	0.027*
C14B	1.22719 (9)	0.9023 (2)	0.29402 (8)	0.0253 (3)
H14C	1.254107	0.930942	0.333302	0.030*
H14D	1.259819	0.913187	0.264598	0.030*
C15B	1.16518 (9)	1.0243 (2)	0.27879 (8)	0.0244 (3)
H15C	1.142238	1.004889	0.237518	0.029*
H15D	1.183327	1.141716	0.281794	0.029*
C16B	1.10992 (8)	1.00217 (18)	0.31992 (7)	0.0214 (3)
H16C	1.068164	1.074585	0.306097	0.026*
H16D	1.130634	1.039286	0.360192	0.026*
O3	1.09074 (6)	0.42756 (14)	0.44180 (5)	0.0212 (2)
O4	0.98127 (6)	0.49881 (13)	0.39947 (5)	0.0199 (2)
O5	0.85421 (6)	−0.01572 (13)	0.44020 (5)	0.0195 (2)
O6	0.88505 (6)	0.07682 (13)	0.53223 (5)	0.0206 (2)
C17	1.02352 (8)	0.40687 (17)	0.43301 (6)	0.0164 (3)
C18	0.99411 (8)	0.26078 (18)	0.46517 (7)	0.0178 (3)
H18A	1.014276	0.153518	0.452931	0.021*
H18B	1.009791	0.274199	0.508155	0.021*
C19	0.91318 (8)	0.24973 (18)	0.45307 (7)	0.0193 (3)
H19A	0.893348	0.349813	0.470664	0.023*
H19B	0.897369	0.254612	0.409875	0.023*
C20	0.88247 (7)	0.09206 (17)	0.47684 (7)	0.0159 (3)
H1AA	0.8420 (12)	−0.345 (3)	0.5019 (10)	0.035 (6)*
H1AB	0.8111 (11)	−0.197 (3)	0.4666 (9)	0.032 (5)*
H2A	0.7963 (14)	−0.008 (3)	0.5381 (11)	0.047 (7)*
H1BA	1.0245 (11)	0.684 (3)	0.3711 (9)	0.029 (5)*
H1BB	1.0611 (11)	0.834 (3)	0.4033 (10)	0.029 (5)*
H2B	1.1162 (14)	0.501 (3)	0.3739 (12)	0.049 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0151 (6)	0.0160 (6)	0.0186 (6)	−0.0014 (4)	0.0011 (5)	0.0014 (5)
O1A	0.0151 (5)	0.0286 (6)	0.0192 (5)	0.0001 (4)	−0.0004 (4)	0.0039 (4)
O2A	0.0225 (6)	0.0188 (5)	0.0285 (6)	−0.0010 (4)	0.0066 (5)	0.0012 (4)
C1A	0.0208 (7)	0.0183 (7)	0.0199 (7)	−0.0008 (6)	−0.0047 (6)	0.0000 (6)
C2A	0.0210 (7)	0.0178 (7)	0.0242 (8)	−0.0011 (6)	−0.0017 (6)	−0.0025 (6)
C3A	0.0214 (8)	0.0163 (7)	0.0345 (9)	−0.0015 (6)	−0.0056 (7)	−0.0028 (6)
C4A	0.0286 (8)	0.0185 (7)	0.0329 (9)	−0.0014 (6)	−0.0124 (7)	0.0023 (6)
C5A	0.0345 (9)	0.0249 (8)	0.0236 (8)	−0.0038 (7)	−0.0065 (7)	0.0050 (6)
C6A	0.0251 (8)	0.0274 (8)	0.0217 (8)	−0.0014 (6)	−0.0015 (6)	0.0030 (6)
C7A	0.0189 (7)	0.0307 (8)	0.0265 (8)	−0.0012 (6)	0.0016 (6)	−0.0022 (7)
C8A	0.0211 (8)	0.0277 (8)	0.0491 (11)	0.0024 (7)	−0.0042 (8)	−0.0029 (8)
C9A	0.0176 (7)	0.0219 (7)	0.0186 (7)	−0.0003 (6)	0.0030 (5)	0.0002 (6)
C10A	0.0178 (7)	0.0185 (7)	0.0179 (7)	0.0006 (5)	0.0023 (5)	0.0000 (5)
C11A	0.0150 (7)	0.0210 (7)	0.0182 (7)	−0.0023 (5)	0.0023 (5)	0.0013 (6)
C12A	0.0184 (7)	0.0184 (7)	0.0198 (7)	−0.0017 (5)	0.0019 (6)	0.0008 (6)
C13A	0.0224 (8)	0.0274 (8)	0.0216 (8)	−0.0004 (6)	0.0061 (6)	−0.0007 (6)
C14A	0.0248 (8)	0.0305 (8)	0.0225 (8)	−0.0024 (7)	0.0071 (6)	0.0048 (6)
C15A	0.0279 (8)	0.0267 (8)	0.0287 (9)	−0.0076 (7)	0.0078 (7)	0.0026 (7)
C16A	0.0265 (8)	0.0201 (7)	0.0261 (8)	−0.0055 (6)	0.0061 (6)	0.0006 (6)
N1B	0.0164 (6)	0.0173 (6)	0.0167 (6)	−0.0002 (5)	0.0026 (5)	0.0000 (5)
O1B	0.0172 (5)	0.0299 (6)	0.0183 (5)	−0.0024 (4)	0.0002 (4)	0.0019 (4)
O2B	0.0263 (6)	0.0158 (5)	0.0247 (6)	−0.0019 (4)	0.0067 (5)	−0.0008 (4)
C1B	0.0201 (7)	0.0177 (7)	0.0234 (8)	−0.0008 (6)	−0.0027 (6)	0.0040 (6)
C2B	0.0203 (7)	0.0173 (7)	0.0252 (8)	0.0009 (6)	−0.0012 (6)	0.0037 (6)
C3B	0.0291 (8)	0.0178 (7)	0.0255 (8)	0.0008 (6)	−0.0033 (7)	0.0020 (6)
C4B	0.0290 (9)	0.0204 (7)	0.0321 (9)	−0.0032 (6)	−0.0100 (7)	0.0039 (6)
C5B	0.0198 (8)	0.0270 (8)	0.0374 (10)	−0.0042 (6)	−0.0043 (7)	0.0077 (7)
C6B	0.0199 (8)	0.0286 (8)	0.0280 (8)	−0.0016 (6)	−0.0001 (6)	0.0064 (7)
C7B	0.0219 (8)	0.0289 (8)	0.0210 (7)	0.0001 (6)	0.0023 (6)	−0.0015 (6)
C8B	0.0378 (10)	0.0298 (8)	0.0268 (9)	0.0011 (7)	−0.0032 (7)	−0.0050 (7)
C9B	0.0162 (7)	0.0267 (8)	0.0227 (8)	0.0007 (6)	0.0053 (6)	0.0027 (6)
C10B	0.0183 (7)	0.0203 (7)	0.0219 (7)	0.0026 (6)	0.0049 (6)	−0.0010 (6)
C11B	0.0165 (7)	0.0184 (7)	0.0155 (7)	0.0001 (5)	0.0031 (5)	0.0006 (5)
C12B	0.0166 (7)	0.0155 (6)	0.0185 (7)	−0.0002 (5)	0.0022 (5)	0.0013 (5)
C13B	0.0208 (7)	0.0227 (7)	0.0245 (8)	0.0029 (6)	0.0082 (6)	0.0019 (6)
C14B	0.0216 (8)	0.0252 (8)	0.0304 (9)	−0.0004 (6)	0.0080 (6)	0.0051 (6)
C15B	0.0278 (8)	0.0201 (7)	0.0273 (8)	0.0012 (6)	0.0099 (7)	0.0065 (6)
C16B	0.0240 (8)	0.0177 (7)	0.0239 (8)	0.0026 (6)	0.0078 (6)	0.0037 (6)
O3	0.0157 (5)	0.0238 (5)	0.0234 (5)	−0.0027 (4)	0.0008 (4)	0.0052 (4)
O4	0.0180 (5)	0.0191 (5)	0.0215 (5)	−0.0011 (4)	−0.0002 (4)	0.0043 (4)
O5	0.0205 (5)	0.0181 (5)	0.0200 (5)	−0.0021 (4)	0.0041 (4)	−0.0013 (4)
O6	0.0223 (5)	0.0210 (5)	0.0180 (5)	−0.0041 (4)	0.0018 (4)	0.0007 (4)
C17	0.0190 (7)	0.0139 (6)	0.0159 (6)	−0.0011 (5)	0.0014 (5)	−0.0016 (5)
C18	0.0165 (7)	0.0159 (6)	0.0203 (7)	−0.0004 (5)	0.0010 (5)	0.0012 (5)
C19	0.0165 (7)	0.0170 (7)	0.0239 (8)	−0.0006 (5)	0.0014 (6)	0.0047 (6)
C20	0.0131 (6)	0.0141 (6)	0.0207 (7)	0.0025 (5)	0.0031 (5)	0.0018 (5)

Geometric parameters (Å, º)

N1A—C10A	1.4954 (19)	O2B—C12B	1.4192 (17)
N1A—C11A	1.5063 (18)	O2B—H2B	0.92 (3)
N1A—H1AA	0.97 (2)	C1B—C2B	1.403 (2)
N1A—H1AB	0.93 (2)	C1B—C6B	1.387 (2)
O1A—C1A	1.3775 (18)	C2B—C3B	1.399 (2)
O1A—C9A	1.4269 (18)	C2B—C7B	1.505 (2)
O2A—C12A	1.4228 (18)	C3B—C4B	1.397 (2)
O2A—H2A	0.92 (3)	C3B—C8B	1.511 (3)
C1A—C2A	1.403 (2)	C4B—H4B	0.9500
C1A—C6A	1.389 (2)	C4B—C5B	1.380 (3)
C2A—C3A	1.403 (2)	C5B—H5B	0.9500
C2A—C7A	1.508 (2)	C5B—C6B	1.392 (2)
C3A—C4A	1.397 (3)	C6B—H6B	0.9500
C3A—C8A	1.511 (2)	C7B—H7BA	0.9800
C4A—H4A	0.9500	C7B—H7BB	0.9800
C4A—C5A	1.380 (3)	C7B—H7BC	0.9800
C5A—H5A	0.9500	C8B—H8BA	0.9800
C5A—C6A	1.391 (2)	C8B—H8BB	0.9800
C6A—H6A	0.9500	C8B—H8BC	0.9800
C7A—H7AA	0.9800	C9B—H9BA	0.9900
C7A—H7AB	0.9800	C9B—H9BB	0.9900
C7A—H7AC	0.9800	C9B—C10B	1.510 (2)
C8A—H8AA	0.9800	C10B—H10C	0.9900
C8A—H8AB	0.9800	C10B—H10D	0.9900
C8A—H8AC	0.9800	C11B—H11B	1.0000
C9A—H9AA	0.9900	C11B—C12B	1.5314 (19)
C9A—H9AB	0.9900	C11B—C16B	1.5315 (19)
C9A—C10A	1.513 (2)	C12B—H12B	1.0000
C10A—H10A	0.9900	C12B—C13B	1.520 (2)
C10A—H10B	0.9900	C13B—H13C	0.9900
C11A—H11A	1.0000	C13B—H13D	0.9900
C11A—C12A	1.531 (2)	C13B—C14B	1.523 (2)
C11A—C16A	1.532 (2)	C14B—H14C	0.9900
C12A—H12A	1.0000	C14B—H14D	0.9900
C12A—C13A	1.522 (2)	C14B—C15B	1.521 (2)
C13A—H13A	0.9900	C15B—H15C	0.9900
C13A—H13B	0.9900	C15B—H15D	0.9900
C13A—C14A	1.523 (2)	C15B—C16B	1.529 (2)
C14A—H14A	0.9900	C16B—H16C	0.9900
C14A—H14B	0.9900	C16B—H16D	0.9900
C14A—C15A	1.525 (2)	O3—C17	1.2729 (18)
C15A—H15A	0.9900	O4—C17	1.2540 (18)
C15A—H15B	0.9900	O5—C20	1.2570 (18)
C15A—C16A	1.531 (2)	O6—C20	1.2696 (18)
C16A—H16A	0.9900	C17—C18	1.5243 (19)
C16A—H16B	0.9900	C18—H18A	0.9900
N1B—C10B	1.4971 (19)	C18—H18B	0.9900
N1B—C11B	1.5022 (18)	C18—C19	1.523 (2)
N1B—H1BA	0.94 (2)	C19—H19A	0.9900
N1B—H1BB	0.94 (2)	C19—H19B	0.9900
O1B—C1B	1.3797 (18)	C19—C20	1.5150 (19)
O1B—C9B	1.4246 (18)
C10A—N1A—C11A	116.67 (11)	O1B—C1B—C6B	123.71 (15)
C10A—N1A—H1AA	108.6 (13)	C6B—C1B—C2B	121.54 (15)
C10A—N1A—H1AB	105.3 (13)	C1B—C2B—C7B	118.75 (14)
C11A—N1A—H1AA	109.2 (13)	C3B—C2B—C1B	118.66 (15)
C11A—N1A—H1AB	112.5 (13)	C3B—C2B—C7B	122.57 (15)
H1AA—N1A—H1AB	103.7 (18)	C2B—C3B—C8B	121.05 (15)
C1A—O1A—C9A	117.56 (12)	C4B—C3B—C2B	119.55 (16)
C12A—O2A—H2A	108.8 (16)	C4B—C3B—C8B	119.39 (15)
O1A—C1A—C2A	114.96 (14)	C3B—C4B—H4B	119.5
O1A—C1A—C6A	123.64 (15)	C5B—C4B—C3B	120.97 (16)
C6A—C1A—C2A	121.40 (14)	C5B—C4B—H4B	119.5
C1A—C2A—C7A	119.15 (14)	C4B—C5B—H5B	119.9
C3A—C2A—C1A	118.53 (15)	C4B—C5B—C6B	120.23 (16)
C3A—C2A—C7A	122.31 (15)	C6B—C5B—H5B	119.9
C2A—C3A—C8A	120.84 (16)	C1B—C6B—C5B	119.04 (16)
C4A—C3A—C2A	119.68 (16)	C1B—C6B—H6B	120.5
C4A—C3A—C8A	119.46 (15)	C5B—C6B—H6B	120.5
C3A—C4A—H4A	119.6	C2B—C7B—H7BA	109.5
C5A—C4A—C3A	120.87 (15)	C2B—C7B—H7BB	109.5
C5A—C4A—H4A	119.6	C2B—C7B—H7BC	109.5
C4A—C5A—H5A	119.9	H7BA—C7B—H7BB	109.5
C4A—C5A—C6A	120.23 (17)	H7BA—C7B—H7BC	109.5
C6A—C5A—H5A	119.9	H7BB—C7B—H7BC	109.5
C1A—C6A—C5A	119.25 (16)	C3B—C8B—H8BA	109.5
C1A—C6A—H6A	120.4	C3B—C8B—H8BB	109.5
C5A—C6A—H6A	120.4	C3B—C8B—H8BC	109.5
C2A—C7A—H7AA	109.5	H8BA—C8B—H8BB	109.5
C2A—C7A—H7AB	109.5	H8BA—C8B—H8BC	109.5
C2A—C7A—H7AC	109.5	H8BB—C8B—H8BC	109.5
H7AA—C7A—H7AB	109.5	O1B—C9B—H9BA	109.8
H7AA—C7A—H7AC	109.5	O1B—C9B—H9BB	109.8
H7AB—C7A—H7AC	109.5	O1B—C9B—C10B	109.31 (12)
C3A—C8A—H8AA	109.5	H9BA—C9B—H9BB	108.3
C3A—C8A—H8AB	109.5	C10B—C9B—H9BA	109.8
C3A—C8A—H8AC	109.5	C10B—C9B—H9BB	109.8
H8AA—C8A—H8AB	109.5	N1B—C10B—C9B	114.66 (12)
H8AA—C8A—H8AC	109.5	N1B—C10B—H10C	108.6
H8AB—C8A—H8AC	109.5	N1B—C10B—H10D	108.6
O1A—C9A—H9AA	110.0	C9B—C10B—H10C	108.6
O1A—C9A—H9AB	110.0	C9B—C10B—H10D	108.6
O1A—C9A—C10A	108.60 (12)	H10C—C10B—H10D	107.6
H9AA—C9A—H9AB	108.4	N1B—C11B—H11B	109.0
C10A—C9A—H9AA	110.0	N1B—C11B—C12B	108.69 (11)
C10A—C9A—H9AB	110.0	N1B—C11B—C16B	110.04 (12)
N1A—C10A—C9A	114.54 (12)	C12B—C11B—H11B	109.0
N1A—C10A—H10A	108.6	C12B—C11B—C16B	111.20 (12)
N1A—C10A—H10B	108.6	C16B—C11B—H11B	109.0
C9A—C10A—H10A	108.6	O2B—C12B—C11B	111.71 (12)
C9A—C10A—H10B	108.6	O2B—C12B—H12B	109.4
H10A—C10A—H10B	107.6	O2B—C12B—C13B	107.90 (12)
N1A—C11A—H11A	108.6	C11B—C12B—H12B	109.4
N1A—C11A—C12A	109.04 (12)	C13B—C12B—C11B	108.85 (12)
N1A—C11A—C16A	109.82 (12)	C13B—C12B—H12B	109.4
C12A—C11A—H11A	108.6	C12B—C13B—H13C	109.4
C12A—C11A—C16A	112.03 (12)	C12B—C13B—H13D	109.4
C16A—C11A—H11A	108.6	C12B—C13B—C14B	111.27 (13)
O2A—C12A—C11A	110.92 (12)	H13C—C13B—H13D	108.0
O2A—C12A—H12A	109.5	C14B—C13B—H13C	109.4
O2A—C12A—C13A	108.29 (12)	C14B—C13B—H13D	109.4
C11A—C12A—H12A	109.5	C13B—C14B—H14C	109.6
C13A—C12A—C11A	109.02 (12)	C13B—C14B—H14D	109.6
C13A—C12A—H12A	109.5	H14C—C14B—H14D	108.1
C12A—C13A—H13A	109.5	C15B—C14B—C13B	110.41 (13)
C12A—C13A—H13B	109.5	C15B—C14B—H14C	109.6
C12A—C13A—C14A	110.75 (13)	C15B—C14B—H14D	109.6
H13A—C13A—H13B	108.1	C14B—C15B—H15C	109.3
C14A—C13A—H13A	109.5	C14B—C15B—H15D	109.3
C14A—C13A—H13B	109.5	C14B—C15B—C16B	111.66 (13)
C13A—C14A—H14A	109.6	H15C—C15B—H15D	107.9
C13A—C14A—H14B	109.6	C16B—C15B—H15C	109.3
C13A—C14A—C15A	110.46 (13)	C16B—C15B—H15D	109.3
H14A—C14A—H14B	108.1	C11B—C16B—H16C	109.3
C15A—C14A—H14A	109.6	C11B—C16B—H16D	109.3
C15A—C14A—H14B	109.6	C15B—C16B—C11B	111.54 (12)
C14A—C15A—H15A	109.3	C15B—C16B—H16C	109.3
C14A—C15A—H15B	109.3	C15B—C16B—H16D	109.3
C14A—C15A—C16A	111.41 (14)	H16C—C16B—H16D	108.0
H15A—C15A—H15B	108.0	O3—C17—C18	117.19 (12)
C16A—C15A—H15A	109.3	O4—C17—O3	123.58 (13)
C16A—C15A—H15B	109.3	O4—C17—C18	119.23 (13)
C11A—C16A—H16A	109.3	C17—C18—H18A	109.0
C11A—C16A—H16B	109.3	C17—C18—H18B	109.0
C15A—C16A—C11A	111.70 (13)	H18A—C18—H18B	107.8
C15A—C16A—H16A	109.3	C19—C18—C17	113.13 (12)
C15A—C16A—H16B	109.3	C19—C18—H18A	109.0
H16A—C16A—H16B	107.9	C19—C18—H18B	109.0
C10B—N1B—C11B	116.45 (11)	C18—C19—H19A	108.6
C10B—N1B—H1BA	108.3 (13)	C18—C19—H19B	108.6
C10B—N1B—H1BB	106.8 (13)	H19A—C19—H19B	107.6
C11B—N1B—H1BA	111.0 (13)	C20—C19—C18	114.69 (12)
C11B—N1B—H1BB	107.3 (13)	C20—C19—H19A	108.6
H1BA—N1B—H1BB	106.4 (18)	C20—C19—H19B	108.6
C1B—O1B—C9B	117.23 (12)	O5—C20—O6	123.35 (13)
C12B—O2B—H2B	107.9 (16)	O5—C20—C19	117.81 (13)
O1B—C1B—C2B	114.74 (13)	O6—C20—C19	118.82 (13)
N1A—C11A—C12A—O2A	62.54 (15)	O1B—C1B—C2B—C3B	178.92 (13)
N1A—C11A—C12A—C13A	−178.31 (12)	O1B—C1B—C2B—C7B	0.2 (2)
N1A—C11A—C16A—C15A	174.59 (13)	O1B—C1B—C6B—C5B	−179.11 (14)
O1A—C1A—C2A—C3A	177.98 (13)	O1B—C9B—C10B—N1B	−65.53 (16)
O1A—C1A—C2A—C7A	−1.4 (2)	O2B—C12B—C13B—C14B	−178.69 (12)
O1A—C1A—C6A—C5A	−179.33 (14)	C1B—O1B—C9B—C10B	−179.18 (12)
O1A—C9A—C10A—N1A	−69.18 (15)	C1B—C2B—C3B—C4B	0.3 (2)
O2A—C12A—C13A—C14A	−179.40 (13)	C1B—C2B—C3B—C8B	−178.50 (14)
C1A—O1A—C9A—C10A	179.46 (12)	C2B—C1B—C6B—C5B	0.6 (2)
C1A—C2A—C3A—C4A	1.8 (2)	C2B—C3B—C4B—C5B	0.5 (2)
C1A—C2A—C3A—C8A	−176.64 (14)	C3B—C4B—C5B—C6B	−0.8 (2)
C2A—C1A—C6A—C5A	0.6 (2)	C4B—C5B—C6B—C1B	0.2 (2)
C2A—C3A—C4A—C5A	−0.4 (2)	C6B—C1B—C2B—C3B	−0.8 (2)
C3A—C4A—C5A—C6A	−1.0 (3)	C6B—C1B—C2B—C7B	−179.54 (14)
C4A—C5A—C6A—C1A	0.9 (2)	C7B—C2B—C3B—C4B	178.92 (15)
C6A—C1A—C2A—C3A	−2.0 (2)	C7B—C2B—C3B—C8B	0.2 (2)
C6A—C1A—C2A—C7A	178.69 (15)	C8B—C3B—C4B—C5B	179.30 (15)
C7A—C2A—C3A—C4A	−178.83 (15)	C9B—O1B—C1B—C2B	−165.12 (13)
C7A—C2A—C3A—C8A	2.7 (2)	C9B—O1B—C1B—C6B	14.6 (2)
C8A—C3A—C4A—C5A	178.10 (15)	C10B—N1B—C11B—C12B	−176.83 (12)
C9A—O1A—C1A—C2A	−166.08 (13)	C10B—N1B—C11B—C16B	61.18 (16)
C9A—O1A—C1A—C6A	13.9 (2)	C11B—N1B—C10B—C9B	77.30 (16)
C10A—N1A—C11A—C12A	−173.91 (12)	C11B—C12B—C13B—C14B	59.91 (16)
C10A—N1A—C11A—C16A	62.99 (16)	C12B—C11B—C16B—C15B	54.82 (17)
C11A—N1A—C10A—C9A	72.84 (16)	C12B—C13B—C14B—C15B	−58.72 (18)
C11A—C12A—C13A—C14A	59.82 (17)	C13B—C14B—C15B—C16B	54.48 (19)
C12A—C11A—C16A—C15A	53.26 (18)	C14B—C15B—C16B—C11B	−53.00 (18)
C12A—C13A—C14A—C15A	−59.92 (18)	C16B—C11B—C12B—O2B	−176.72 (12)
C13A—C14A—C15A—C16A	55.42 (19)	C16B—C11B—C12B—C13B	−57.67 (16)
C14A—C15A—C16A—C11A	−52.20 (19)	O3—C17—C18—C19	178.42 (13)
C16A—C11A—C12A—O2A	−175.68 (12)	O4—C17—C18—C19	−2.02 (19)
C16A—C11A—C12A—C13A	−56.53 (16)	C17—C18—C19—C20	171.46 (12)
N1B—C11B—C12B—O2B	62.01 (15)	C18—C19—C20—O5	−110.33 (15)
N1B—C11B—C12B—C13B	−178.94 (12)	C18—C19—C20—O6	71.19 (18)
N1B—C11B—C16B—C15B	175.30 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AA···O3^i	0.97 (2)	1.79 (2)	2.7516 (17)	171 (2)
N1A—H1AB···O5	0.93 (2)	1.81 (2)	2.7021 (16)	161 (2)
O2A—H2A···O6	0.92 (3)	1.84 (3)	2.7494 (16)	171 (2)
N1B—H1BA···O4	0.94 (2)	1.85 (2)	2.7446 (16)	157.9 (19)
N1B—H1BB···O6^ii	0.94 (2)	1.80 (2)	2.7416 (17)	172.0 (19)
O2B—H2B···O3	0.92 (3)	1.80 (3)	2.7139 (16)	174 (2)

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

Bis{D,L-trans-N-[(2,3-dimethylphenoxy)ethyl]-1-hydroxycyclohexan-2-aminium} succinate (1p)

Crystal data

2C16H26NO2^+·C4H4O4^2^−	F(000) = 2800
Mr = 644.82	Dx = 1.208 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 18.26079 (7) Å	Cell parameters from 94974 reflections
b = 16.54776 (6) Å	θ = 3.3–77.2°
c = 23.56421 (9) Å	µ = 0.68 mm^−1
β = 95.0196 (4)°	T = 100 K
V = 7093.21 (5) Å^3	Plate, clear colourless
Z = 8	0.53 × 0.30 × 0.04 mm

Data collection

Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector	14961 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	11575 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.037
Detector resolution: 10.0000 pixels mm^-1	θmax = 77.4°, θmin = 2.9°
ω scans	h = −23→23
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2023)	k = −20→20
Tmin = 0.221, Tmax = 1.000	l = −29→29
254839 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.071	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.230	w = 1/[σ^2(Fo^2) + (0.1601P)^2 + 1.0731P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
14961 reflections	Δρmax = 1.00 e Å^−3
909 parameters	Δρmin = −0.28 e Å^−3
0 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.89267 (5)	0.30401 (5)	0.65038 (3)	0.0246 (2)
C1A	0.92944 (6)	0.27407 (7)	0.69923 (5)	0.0194 (2)
C2A	0.91516 (7)	0.31344 (7)	0.74975 (5)	0.0229 (3)
C3A	0.94971 (7)	0.28618 (8)	0.80133 (5)	0.0264 (3)
C4A	0.99754 (7)	0.21964 (9)	0.80159 (5)	0.0326 (3)
H4A	1.020488	0.200318	0.836723	0.039*
C5A	1.01158 (7)	0.18194 (8)	0.75130 (5)	0.0305 (3)
H5A	1.044620	0.137529	0.752135	0.037*
C6A	0.97778 (7)	0.20851 (8)	0.69965 (5)	0.0269 (3)
H6A	0.987337	0.182559	0.665102	0.032*
C7A	0.86553 (7)	0.38622 (8)	0.74757 (5)	0.0305 (3)
H7AA	0.895376	0.435406	0.751953	0.046*
H7AB	0.833066	0.383037	0.778486	0.046*
H7AC	0.835845	0.387583	0.710870	0.046*
C8A	0.93590 (9)	0.32691 (10)	0.85628 (6)	0.0389 (3)
H8AA	0.945899	0.384883	0.853393	0.058*
H8AB	0.968276	0.303610	0.887415	0.058*
H8AC	0.884517	0.318841	0.863929	0.058*
N1A	0.86862 (5)	0.28221 (6)	0.49556 (4)	0.0133 (2)
O2A	0.71417 (4)	0.24369 (5)	0.48377 (4)	0.01783 (19)
C9A	0.90616 (6)	0.26752 (7)	0.59780 (5)	0.0178 (2)
C10A	0.85311 (6)	0.30842 (7)	0.55379 (5)	0.0174 (2)
H10A	0.801984	0.294043	0.560599	0.021*
H10B	0.858377	0.367818	0.557130	0.021*
C11A	0.81683 (6)	0.31779 (7)	0.44886 (5)	0.0147 (2)
H11A	0.797966	0.370581	0.462229	0.018*
C12A	0.75171 (6)	0.26087 (7)	0.43495 (5)	0.0174 (2)
H12A	0.771418	0.208775	0.421080	0.021*
C13A	0.70031 (6)	0.29680 (8)	0.38651 (5)	0.0244 (3)
H13A	0.659649	0.258440	0.376407	0.029*
H13B	0.678626	0.347455	0.399854	0.029*
C14A	0.74023 (7)	0.31470 (10)	0.33338 (5)	0.0314 (3)
H14A	0.756707	0.263368	0.317076	0.038*
H14B	0.705950	0.341415	0.304355	0.038*
C15A	0.80668 (7)	0.36939 (9)	0.34811 (5)	0.0274 (3)
H15A	0.833773	0.376960	0.313902	0.033*
H15B	0.789677	0.423071	0.360073	0.033*
C16A	0.85808 (6)	0.33274 (8)	0.39603 (5)	0.0207 (3)
H16A	0.899747	0.369941	0.405786	0.025*
H16B	0.878198	0.281056	0.383020	0.025*
O1B	0.62327 (5)	0.53181 (6)	0.35111 (4)	0.0284 (2)
C1B	0.57595 (7)	0.52570 (7)	0.30263 (5)	0.0207 (3)
C2B	0.60691 (7)	0.54262 (7)	0.25163 (5)	0.0258 (3)
C3B	0.56117 (8)	0.54209 (8)	0.20060 (5)	0.0270 (3)
C4B	0.48702 (8)	0.52425 (8)	0.20191 (6)	0.0351 (3)
H4B	0.455973	0.523981	0.167388	0.042*
C5B	0.45774 (7)	0.50693 (8)	0.25253 (6)	0.0351 (3)
H5B	0.406912	0.494637	0.252458	0.042*
C6B	0.50186 (7)	0.50730 (8)	0.30355 (6)	0.0287 (3)
H6B	0.481784	0.495197	0.338420	0.034*
C7B	0.68752 (7)	0.56401 (10)	0.25339 (6)	0.0363 (3)
H7BA	0.693370	0.622717	0.256876	0.055*
H7BB	0.707251	0.545606	0.218255	0.055*
H7BC	0.714218	0.537577	0.286193	0.055*
C8B	0.59046 (9)	0.56560 (9)	0.14523 (6)	0.0377 (3)
H8BA	0.550241	0.565567	0.114833	0.057*
H8BB	0.628168	0.526790	0.135988	0.057*
H8BC	0.612049	0.619780	0.148794	0.057*
N1B	0.63245 (5)	0.53319 (6)	0.50653 (4)	0.0140 (2)
O2B	0.78800 (4)	0.49426 (5)	0.52173 (4)	0.0199 (2)
C9B	0.59334 (6)	0.52295 (8)	0.40417 (5)	0.0199 (2)
C10B	0.65442 (6)	0.54844 (7)	0.44813 (5)	0.0192 (2)
H10C	0.699671	0.517698	0.442335	0.023*
H10D	0.665013	0.606644	0.443579	0.023*
C11B	0.68353 (6)	0.56908 (7)	0.55356 (5)	0.0151 (2)
H11B	0.702782	0.621682	0.540188	0.018*
C12B	0.74841 (6)	0.51238 (7)	0.56923 (5)	0.0176 (2)
H12B	0.728265	0.460545	0.583156	0.021*
C13B	0.79827 (7)	0.54926 (8)	0.61823 (5)	0.0253 (3)
H13C	0.838871	0.511248	0.629346	0.030*
H13D	0.820171	0.599829	0.604938	0.030*
C14B	0.75664 (8)	0.56769 (10)	0.67024 (6)	0.0329 (3)
H14C	0.739678	0.516523	0.686476	0.040*
H14D	0.790027	0.594754	0.699700	0.040*
C15B	0.69054 (7)	0.62210 (9)	0.65400 (5)	0.0292 (3)
H15C	0.707855	0.675641	0.642037	0.035*
H15D	0.662298	0.630052	0.687560	0.035*
C16B	0.64068 (6)	0.58468 (8)	0.60547 (5)	0.0212 (3)
H16C	0.599132	0.621640	0.594734	0.025*
H16D	0.620262	0.533129	0.618435	0.025*
O1C	0.89407 (5)	0.55601 (5)	0.14862 (3)	0.0252 (2)
C1C	0.93045 (6)	0.52521 (7)	0.19733 (5)	0.0196 (2)
C2C	0.91631 (6)	0.56439 (7)	0.24801 (5)	0.0237 (3)
C3C	0.95057 (7)	0.53626 (8)	0.29942 (5)	0.0266 (3)
C4C	0.99806 (7)	0.46964 (9)	0.29953 (5)	0.0328 (3)
H4C	1.020866	0.450026	0.334625	0.039*
C5C	1.01207 (7)	0.43222 (8)	0.24924 (5)	0.0311 (3)
H5C	1.044784	0.387524	0.249930	0.037*
C6C	0.97846 (7)	0.45970 (8)	0.19757 (5)	0.0273 (3)
H6C	0.988100	0.434146	0.162902	0.033*
C7C	0.86660 (7)	0.63710 (8)	0.24623 (6)	0.0313 (3)
H7CA	0.896389	0.686278	0.251098	0.047*
H7CB	0.833950	0.633355	0.276994	0.047*
H7CC	0.837115	0.638987	0.209454	0.047*
C8C	0.93727 (9)	0.57706 (10)	0.35451 (6)	0.0407 (4)
H8CA	0.886119	0.568554	0.362642	0.061*
H8CB	0.946781	0.635107	0.351424	0.061*
H8CC	0.970249	0.554134	0.385430	0.061*
N1C	0.87053 (5)	0.53171 (6)	−0.00608 (4)	0.0137 (2)
O2C	0.71669 (4)	0.49023 (5)	−0.01713 (4)	0.0197 (2)
C9C	0.90742 (6)	0.51928 (7)	0.09600 (5)	0.0184 (2)
C10C	0.85479 (6)	0.56004 (7)	0.05167 (5)	0.0183 (2)
H10E	0.803485	0.546606	0.058542	0.022*
H10F	0.860774	0.619423	0.054263	0.022*
C11C	0.81833 (6)	0.56397 (7)	−0.05360 (5)	0.0157 (2)
H11C	0.798164	0.616818	−0.041496	0.019*
C12C	0.75487 (6)	0.50476 (7)	−0.06595 (5)	0.0180 (2)
H12C	0.776100	0.452206	−0.077544	0.022*
C13C	0.70319 (7)	0.53537 (9)	−0.11606 (5)	0.0266 (3)
H13E	0.663943	0.494919	−0.125068	0.032*
H13F	0.679576	0.586078	−0.104817	0.032*
C14C	0.74325 (8)	0.55099 (10)	−0.16937 (6)	0.0317 (3)
H14E	0.708553	0.574443	−0.199580	0.038*
H14F	0.761754	0.499249	−0.183636	0.038*
C15C	0.80769 (7)	0.60911 (9)	−0.15588 (5)	0.0289 (3)
H15E	0.835042	0.615612	−0.190054	0.035*
H15F	0.788592	0.662780	−0.145878	0.035*
C16C	0.85972 (6)	0.57767 (8)	−0.10645 (5)	0.0216 (3)
H16E	0.899750	0.617241	−0.097569	0.026*
H16F	0.882129	0.526221	−0.117615	0.026*
O1D	0.62236 (5)	0.28362 (6)	−0.14679 (4)	0.0292 (2)
C1D	0.57515 (7)	0.27621 (7)	−0.19533 (5)	0.0210 (3)
C2D	0.60638 (7)	0.29247 (7)	−0.24641 (5)	0.0263 (3)
C3D	0.56061 (8)	0.29146 (8)	−0.29734 (6)	0.0274 (3)
C4D	0.48648 (8)	0.27317 (8)	−0.29618 (6)	0.0346 (3)
H4D	0.455446	0.272700	−0.330711	0.042*
C5D	0.45741 (7)	0.25567 (8)	−0.24548 (6)	0.0349 (3)
H5D	0.406713	0.242732	−0.245546	0.042*
C6D	0.50134 (7)	0.25674 (8)	−0.19444 (6)	0.0290 (3)
H6D	0.481338	0.244414	−0.159575	0.035*
C7D	0.68691 (8)	0.31415 (10)	−0.24484 (6)	0.0366 (3)
H7DA	0.692327	0.373067	−0.244207	0.055*
H7DB	0.707434	0.292343	−0.278719	0.055*
H7DC	0.713198	0.291088	−0.210566	0.055*
C8D	0.59001 (9)	0.31461 (10)	−0.35278 (6)	0.0387 (3)
H8DA	0.627246	0.275298	−0.362126	0.058*
H8DB	0.612207	0.368495	−0.349209	0.058*
H8DC	0.549712	0.315128	−0.383116	0.058*
N1D	0.63067 (5)	0.28270 (6)	0.00841 (4)	0.0142 (2)
O2D	0.78583 (4)	0.24007 (5)	0.02333 (4)	0.0211 (2)
C9D	0.59220 (6)	0.27492 (7)	−0.09384 (5)	0.0201 (2)
H9DA	0.577757	0.218122	−0.087752	0.024*
H9DB	0.548429	0.309858	−0.092167	0.024*
C10D	0.65290 (6)	0.30053 (7)	−0.04956 (5)	0.0200 (2)
H10G	0.698704	0.271017	−0.055691	0.024*
H10H	0.662458	0.359107	−0.053200	0.024*
C11D	0.68229 (6)	0.31508 (7)	0.05626 (5)	0.0157 (2)
H11D	0.703151	0.367512	0.044044	0.019*
C12D	0.74528 (6)	0.25577 (7)	0.07069 (5)	0.0192 (2)
H12D	0.723388	0.203528	0.082221	0.023*
C13D	0.79531 (7)	0.28704 (9)	0.12154 (5)	0.0266 (3)
H13G	0.834095	0.246497	0.131796	0.032*
H13H	0.819659	0.337332	0.110371	0.032*
C14D	0.75346 (8)	0.30401 (10)	0.17350 (6)	0.0320 (3)
H14G	0.787279	0.327863	0.204134	0.038*
H14H	0.734185	0.252702	0.187854	0.038*
C15D	0.68980 (7)	0.36212 (9)	0.15821 (5)	0.0292 (3)
H15G	0.661227	0.369417	0.191659	0.035*
H15H	0.709535	0.415475	0.148190	0.035*
C16D	0.63924 (6)	0.33021 (8)	0.10814 (5)	0.0219 (3)
H16G	0.599689	0.369962	0.098140	0.026*
H16H	0.616079	0.279194	0.119284	0.026*
O3A	0.49143 (4)	0.59867 (5)	0.49896 (4)	0.0251 (2)
O4A	0.37366 (4)	0.63199 (5)	0.49209 (3)	0.01754 (19)
O5A	0.62729 (4)	0.86607 (5)	0.50012 (4)	0.01796 (19)
O6A	0.50952 (4)	0.89986 (5)	0.49423 (4)	0.0234 (2)
C21A	0.44164 (6)	0.65002 (6)	0.49704 (4)	0.0136 (2)
C22A	0.46054 (6)	0.73959 (6)	0.50114 (5)	0.0154 (2)
H22A	0.428518	0.769178	0.472095	0.018*
H22B	0.449462	0.759657	0.539032	0.018*
C23A	0.54014 (6)	0.75888 (6)	0.49276 (5)	0.0159 (2)
H23A	0.551328	0.738218	0.455042	0.019*
H23B	0.572100	0.729670	0.522049	0.019*
C24A	0.55925 (6)	0.84834 (6)	0.49619 (4)	0.0137 (2)
O3B	0.87421 (4)	0.61830 (5)	0.49389 (4)	0.01846 (19)
O4B	0.99224 (4)	0.65050 (5)	0.50150 (4)	0.0244 (2)
C21B	0.94197 (6)	0.59967 (6)	0.49902 (4)	0.0138 (2)
C22B	0.96000 (5)	0.50998 (6)	0.50295 (5)	0.0160 (2)
H22C	0.946660	0.489437	0.540136	0.019*
H22D	0.929218	0.481141	0.472752	0.019*
O3C	0.37236 (4)	0.38423 (5)	−0.00214 (4)	0.01763 (19)
O4C	0.48986 (4)	0.34945 (5)	0.00376 (4)	0.0245 (2)
C21C	0.44055 (6)	0.40139 (6)	0.00191 (4)	0.0138 (2)
C22C	0.46052 (5)	0.49074 (6)	0.00540 (5)	0.0158 (2)
H22E	0.427431	0.520649	−0.022750	0.019*
H22F	0.451572	0.510978	0.043723	0.019*
H1AA	0.9156 (9)	0.2974 (9)	0.4917 (7)	0.021 (4)*
H1AB	0.8684 (8)	0.2306 (11)	0.4941 (6)	0.019 (4)*
H2A	0.6849 (12)	0.2856 (12)	0.4916 (8)	0.043 (5)*
H9AA	0.9560 (8)	0.2754 (9)	0.5888 (6)	0.024 (3)*
H9AB	0.8950 (9)	0.2097 (10)	0.6000 (6)	0.030 (4)*
H1BA	0.6294 (8)	0.4803 (11)	0.5112 (6)	0.020 (4)*
H1BB	0.5855 (9)	0.5554 (10)	0.5070 (7)	0.024 (4)*
H2B	0.8163 (12)	0.5385 (13)	0.5121 (9)	0.048 (5)*
H9BA	0.5781 (8)	0.4685 (9)	0.4104 (6)	0.030 (4)*
H9BB	0.5510 (8)	0.5578 (9)	0.4054 (6)	0.029 (4)*
H1CA	0.9166 (9)	0.5479 (9)	−0.0108 (7)	0.022 (4)*
H1CB	0.8707 (8)	0.4798 (11)	−0.0062 (7)	0.021 (4)*
H2C	0.6865 (11)	0.5314 (12)	−0.0110 (8)	0.040 (5)*
H9CA	0.8959 (9)	0.4620 (10)	0.0982 (6)	0.032 (4)*
H9CB	0.9581 (8)	0.5275 (8)	0.0874 (6)	0.020 (3)*
H1DA	0.6268 (9)	0.2296 (11)	0.0105 (7)	0.022 (4)*
H1DB	0.5837 (9)	0.3048 (9)	0.0104 (6)	0.020 (4)*
H2D	0.8142 (12)	0.2840 (12)	0.0163 (8)	0.044 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0291 (5)	0.0259 (5)	0.0180 (4)	0.0089 (3)	−0.0018 (3)	−0.0031 (3)
C1A	0.0192 (6)	0.0176 (5)	0.0211 (6)	−0.0036 (4)	−0.0003 (4)	0.0018 (4)
C2A	0.0223 (6)	0.0256 (6)	0.0209 (5)	−0.0047 (4)	0.0019 (4)	−0.0008 (4)
C3A	0.0266 (6)	0.0313 (7)	0.0211 (6)	−0.0107 (5)	0.0018 (5)	0.0015 (5)
C4A	0.0291 (6)	0.0382 (7)	0.0294 (6)	−0.0069 (5)	−0.0028 (5)	0.0095 (5)
C5A	0.0252 (6)	0.0283 (6)	0.0377 (7)	0.0001 (5)	0.0001 (5)	0.0074 (5)
C6A	0.0252 (6)	0.0265 (6)	0.0289 (6)	0.0010 (5)	0.0021 (5)	0.0013 (5)
C7A	0.0320 (7)	0.0283 (6)	0.0319 (6)	−0.0015 (5)	0.0074 (5)	−0.0045 (5)
C8A	0.0483 (9)	0.0465 (8)	0.0215 (6)	−0.0051 (7)	0.0010 (6)	−0.0020 (6)
N1A	0.0099 (4)	0.0124 (5)	0.0176 (5)	0.0000 (3)	0.0004 (3)	0.0002 (3)
O2A	0.0128 (4)	0.0157 (4)	0.0256 (4)	−0.0004 (3)	0.0049 (3)	0.0002 (3)
C9A	0.0200 (6)	0.0163 (5)	0.0168 (5)	0.0018 (4)	−0.0010 (4)	−0.0026 (4)
C10A	0.0162 (5)	0.0173 (5)	0.0185 (5)	0.0023 (4)	−0.0001 (4)	−0.0018 (4)
C11A	0.0117 (5)	0.0143 (5)	0.0180 (5)	0.0003 (4)	0.0004 (4)	0.0014 (4)
C12A	0.0143 (5)	0.0160 (5)	0.0222 (5)	−0.0010 (4)	0.0031 (4)	−0.0024 (4)
C13A	0.0153 (5)	0.0348 (7)	0.0223 (6)	−0.0004 (4)	−0.0027 (4)	−0.0003 (5)
C14A	0.0259 (6)	0.0469 (8)	0.0207 (6)	−0.0043 (6)	−0.0018 (5)	0.0010 (5)
C15A	0.0285 (6)	0.0338 (7)	0.0195 (6)	−0.0051 (5)	0.0004 (5)	0.0050 (5)
C16A	0.0183 (5)	0.0246 (6)	0.0197 (5)	−0.0039 (4)	0.0049 (4)	−0.0007 (4)
O1B	0.0206 (4)	0.0450 (6)	0.0197 (4)	−0.0089 (4)	0.0022 (3)	−0.0005 (4)
C1B	0.0202 (6)	0.0185 (6)	0.0229 (6)	0.0000 (4)	−0.0012 (4)	−0.0015 (4)
C2B	0.0282 (6)	0.0246 (6)	0.0246 (6)	−0.0048 (5)	0.0015 (5)	−0.0009 (4)
C3B	0.0355 (7)	0.0216 (6)	0.0232 (6)	0.0037 (5)	−0.0023 (5)	0.0000 (5)
C4B	0.0342 (7)	0.0316 (7)	0.0368 (7)	0.0032 (5)	−0.0121 (5)	0.0000 (5)
C5B	0.0238 (6)	0.0344 (7)	0.0459 (8)	−0.0012 (5)	−0.0048 (5)	−0.0024 (6)
C6B	0.0230 (6)	0.0276 (6)	0.0354 (6)	−0.0027 (5)	0.0017 (5)	0.0000 (5)
C7B	0.0303 (7)	0.0501 (8)	0.0293 (6)	−0.0107 (6)	0.0057 (5)	−0.0001 (6)
C8B	0.0519 (9)	0.0369 (8)	0.0239 (6)	0.0026 (6)	0.0008 (6)	0.0007 (5)
N1B	0.0104 (4)	0.0124 (5)	0.0194 (5)	−0.0009 (3)	0.0019 (3)	0.0002 (3)
O2B	0.0140 (4)	0.0168 (4)	0.0296 (5)	0.0006 (3)	0.0061 (3)	−0.0005 (3)
C9B	0.0168 (5)	0.0235 (6)	0.0193 (6)	−0.0028 (4)	0.0017 (4)	0.0017 (4)
C10B	0.0168 (5)	0.0216 (6)	0.0195 (5)	−0.0043 (4)	0.0028 (4)	0.0005 (4)
C11B	0.0123 (5)	0.0138 (5)	0.0193 (5)	−0.0002 (4)	0.0016 (4)	−0.0008 (4)
C12B	0.0142 (5)	0.0145 (5)	0.0242 (6)	0.0008 (4)	0.0026 (4)	0.0027 (4)
C13B	0.0164 (5)	0.0327 (7)	0.0260 (6)	0.0012 (5)	−0.0022 (4)	−0.0004 (5)
C14B	0.0285 (7)	0.0474 (8)	0.0221 (6)	0.0045 (6)	−0.0025 (5)	−0.0010 (5)
C15B	0.0297 (7)	0.0361 (7)	0.0217 (6)	0.0042 (5)	0.0017 (5)	−0.0062 (5)
C16B	0.0183 (5)	0.0251 (6)	0.0207 (5)	0.0043 (4)	0.0051 (4)	0.0002 (4)
O1C	0.0300 (5)	0.0266 (5)	0.0186 (4)	0.0094 (3)	−0.0001 (3)	−0.0028 (3)
C1C	0.0189 (6)	0.0189 (6)	0.0207 (6)	−0.0029 (4)	0.0001 (4)	0.0011 (4)
C2C	0.0225 (6)	0.0255 (6)	0.0232 (6)	−0.0042 (4)	0.0034 (4)	−0.0018 (4)
C3C	0.0267 (6)	0.0312 (7)	0.0221 (6)	−0.0106 (5)	0.0027 (5)	0.0013 (5)
C4C	0.0309 (7)	0.0375 (7)	0.0289 (6)	−0.0069 (5)	−0.0029 (5)	0.0077 (5)
C5C	0.0268 (6)	0.0291 (7)	0.0367 (7)	0.0001 (5)	−0.0002 (5)	0.0067 (5)
C6C	0.0268 (6)	0.0271 (6)	0.0280 (6)	0.0016 (5)	0.0024 (5)	−0.0002 (5)
C7C	0.0332 (7)	0.0286 (6)	0.0332 (6)	−0.0011 (5)	0.0087 (5)	−0.0055 (5)
C8C	0.0507 (9)	0.0490 (9)	0.0223 (6)	−0.0040 (7)	0.0033 (6)	−0.0035 (6)
N1C	0.0103 (4)	0.0124 (5)	0.0181 (5)	0.0003 (3)	0.0005 (3)	0.0003 (3)
O2C	0.0127 (4)	0.0167 (4)	0.0304 (5)	−0.0004 (3)	0.0051 (3)	0.0018 (3)
C9C	0.0201 (6)	0.0172 (5)	0.0174 (5)	0.0020 (4)	−0.0004 (4)	−0.0034 (4)
C10C	0.0172 (5)	0.0180 (5)	0.0194 (5)	0.0027 (4)	0.0007 (4)	−0.0018 (4)
C11C	0.0116 (5)	0.0163 (5)	0.0191 (5)	−0.0008 (4)	0.0001 (4)	0.0019 (4)
C12C	0.0138 (5)	0.0144 (5)	0.0259 (6)	−0.0007 (4)	0.0021 (4)	−0.0020 (4)
C13C	0.0140 (5)	0.0371 (7)	0.0278 (6)	−0.0020 (5)	−0.0032 (5)	−0.0009 (5)
C14C	0.0253 (6)	0.0461 (8)	0.0227 (6)	−0.0031 (5)	−0.0031 (5)	−0.0030 (5)
C15C	0.0250 (6)	0.0399 (7)	0.0211 (6)	−0.0053 (5)	−0.0023 (5)	0.0054 (5)
C16C	0.0169 (5)	0.0303 (6)	0.0179 (5)	−0.0039 (4)	0.0031 (4)	−0.0010 (4)
O1D	0.0216 (4)	0.0457 (6)	0.0205 (4)	−0.0091 (4)	0.0030 (3)	0.0004 (4)
C1D	0.0214 (6)	0.0187 (6)	0.0226 (6)	0.0006 (4)	0.0001 (4)	−0.0004 (4)
C2D	0.0283 (6)	0.0250 (6)	0.0257 (6)	−0.0045 (5)	0.0029 (5)	0.0009 (5)
C3D	0.0360 (7)	0.0223 (6)	0.0235 (6)	0.0025 (5)	−0.0003 (5)	0.0005 (5)
C4D	0.0336 (7)	0.0333 (7)	0.0349 (7)	0.0030 (5)	−0.0084 (5)	−0.0004 (5)
C5D	0.0253 (6)	0.0338 (7)	0.0446 (8)	−0.0015 (5)	−0.0024 (5)	−0.0013 (6)
C6D	0.0243 (6)	0.0290 (6)	0.0340 (7)	−0.0031 (5)	0.0037 (5)	0.0003 (5)
C7D	0.0312 (7)	0.0488 (8)	0.0306 (7)	−0.0107 (6)	0.0072 (5)	0.0009 (6)
C8D	0.0513 (9)	0.0399 (8)	0.0246 (6)	0.0019 (7)	0.0027 (6)	0.0022 (5)
N1D	0.0110 (4)	0.0122 (5)	0.0194 (5)	−0.0010 (3)	0.0018 (3)	−0.0015 (3)
O2D	0.0137 (4)	0.0164 (4)	0.0339 (5)	0.0006 (3)	0.0069 (3)	−0.0031 (3)
C9D	0.0175 (5)	0.0238 (6)	0.0191 (6)	−0.0028 (4)	0.0023 (4)	0.0011 (4)
C10D	0.0173 (5)	0.0222 (6)	0.0207 (5)	−0.0044 (4)	0.0033 (4)	0.0007 (4)
C11D	0.0123 (5)	0.0147 (5)	0.0201 (5)	0.0002 (4)	0.0008 (4)	−0.0025 (4)
C12D	0.0143 (5)	0.0151 (5)	0.0285 (6)	−0.0002 (4)	0.0034 (4)	0.0020 (4)
C13D	0.0155 (5)	0.0346 (7)	0.0289 (6)	0.0024 (5)	−0.0019 (5)	0.0007 (5)
C14D	0.0261 (7)	0.0454 (8)	0.0238 (6)	0.0017 (6)	−0.0022 (5)	0.0026 (5)
C15D	0.0267 (6)	0.0386 (7)	0.0220 (6)	0.0051 (5)	−0.0003 (5)	−0.0064 (5)
C16D	0.0174 (5)	0.0284 (6)	0.0201 (5)	0.0039 (4)	0.0040 (4)	−0.0005 (4)
O3A	0.0125 (4)	0.0123 (4)	0.0507 (6)	0.0014 (3)	0.0034 (4)	0.0017 (3)
O4A	0.0106 (4)	0.0132 (4)	0.0290 (4)	−0.0022 (3)	0.0026 (3)	0.0005 (3)
O5A	0.0102 (4)	0.0134 (4)	0.0301 (4)	−0.0016 (3)	0.0013 (3)	0.0004 (3)
O6A	0.0123 (4)	0.0130 (4)	0.0449 (5)	0.0014 (3)	0.0032 (3)	0.0009 (3)
C21A	0.0129 (5)	0.0115 (5)	0.0166 (5)	−0.0010 (4)	0.0021 (4)	0.0001 (4)
C22A	0.0110 (5)	0.0106 (5)	0.0248 (5)	−0.0013 (4)	0.0034 (4)	−0.0012 (4)
C23A	0.0113 (5)	0.0106 (5)	0.0262 (6)	−0.0014 (4)	0.0039 (4)	−0.0011 (4)
C24A	0.0126 (5)	0.0112 (5)	0.0173 (5)	−0.0011 (4)	0.0010 (4)	0.0003 (4)
O3B	0.0108 (4)	0.0125 (4)	0.0322 (4)	0.0017 (3)	0.0024 (3)	0.0007 (3)
O4B	0.0128 (4)	0.0122 (4)	0.0482 (5)	−0.0016 (3)	0.0037 (4)	−0.0012 (3)
C21B	0.0127 (5)	0.0112 (5)	0.0176 (5)	0.0007 (4)	0.0020 (4)	0.0005 (4)
C22B	0.0116 (5)	0.0099 (5)	0.0268 (6)	0.0010 (4)	0.0044 (4)	0.0024 (4)
O3C	0.0106 (4)	0.0130 (4)	0.0294 (4)	−0.0016 (3)	0.0022 (3)	0.0010 (3)
O4C	0.0127 (4)	0.0122 (4)	0.0487 (5)	0.0014 (3)	0.0032 (4)	0.0011 (3)
C21C	0.0123 (5)	0.0120 (5)	0.0171 (5)	−0.0004 (4)	0.0011 (4)	0.0006 (4)
C22C	0.0109 (5)	0.0113 (5)	0.0254 (5)	−0.0011 (4)	0.0037 (4)	−0.0012 (4)

Geometric parameters (Å, º)

O1A—C1A	1.3732 (14)	C6C—H6C	0.9500
O1A—C9A	1.4191 (13)	C7C—H7CA	0.9800
C1A—C2A	1.4014 (16)	C7C—H7CB	0.9800
C1A—C6A	1.3983 (17)	C7C—H7CC	0.9800
C2A—C3A	1.3946 (17)	C8C—H8CA	0.9800
C2A—C7A	1.5053 (17)	C8C—H8CB	0.9800
C3A—C4A	1.405 (2)	C8C—H8CC	0.9800
C3A—C8A	1.5007 (18)	N1C—C10C	1.4908 (14)
C4A—H4A	0.9500	N1C—C11C	1.5036 (13)
C4A—C5A	1.3828 (19)	N1C—H1CA	0.898 (17)
C5A—H5A	0.9500	N1C—H1CB	0.859 (18)
C5A—C6A	1.3871 (17)	O2C—C12C	1.4168 (13)
C6A—H6A	0.9500	O2C—H2C	0.90 (2)
C7A—H7AA	0.9800	C9C—C10C	1.5146 (15)
C7A—H7AB	0.9800	C9C—H9CA	0.974 (16)
C7A—H7AC	0.9800	C9C—H9CB	0.975 (14)
C8A—H8AA	0.9800	C10C—H10E	0.9900
C8A—H8AB	0.9800	C10C—H10F	0.9900
C8A—H8AC	0.9800	C11C—H11C	1.0000
N1A—C10A	1.4897 (14)	C11C—C12C	1.5260 (15)
N1A—C11A	1.5067 (13)	C11C—C16C	1.5292 (15)
N1A—H1AA	0.907 (17)	C12C—H12C	1.0000
N1A—H1AB	0.854 (18)	C12C—C13C	1.5318 (16)
O2A—C12A	1.4185 (13)	C13C—H13E	0.9900
O2A—H2A	0.91 (2)	C13C—H13F	0.9900
C9A—C10A	1.5154 (15)	C13C—C14C	1.5299 (18)
C9A—H9AA	0.961 (15)	C14C—H14E	0.9900
C9A—H9AB	0.981 (16)	C14C—H14F	0.9900
C10A—H10A	0.9900	C14C—C15C	1.5315 (18)
C10A—H10B	0.9900	C15C—H15E	0.9900
C11A—H11A	1.0000	C15C—H15F	0.9900
C11A—C12A	1.5299 (15)	C15C—C16C	1.5285 (17)
C11A—C16A	1.5306 (14)	C16C—H16E	0.9900
C12A—H12A	1.0000	C16C—H16F	0.9900
C12A—C13A	1.5328 (16)	O1D—C1D	1.3762 (15)
C13A—H13A	0.9900	O1D—C9D	1.4145 (13)
C13A—H13B	0.9900	C1D—C2D	1.4026 (17)
C13A—C14A	1.5317 (17)	C1D—C6D	1.3876 (17)
C14A—H14A	0.9900	C2D—C3D	1.4012 (18)
C14A—H14B	0.9900	C2D—C7D	1.5109 (18)
C14A—C15A	1.5291 (18)	C3D—C4D	1.390 (2)
C15A—H15A	0.9900	C3D—C8D	1.5049 (18)
C15A—H15B	0.9900	C4D—H4D	0.9500
C15A—C16A	1.5291 (17)	C4D—C5D	1.380 (2)
C16A—H16A	0.9900	C5D—H5D	0.9500
C16A—H16B	0.9900	C5D—C6D	1.3862 (19)
O1B—C1B	1.3745 (14)	C6D—H6D	0.9500
O1B—C9B	1.4154 (13)	C7D—H7DA	0.9800
C1B—C2B	1.4002 (17)	C7D—H7DB	0.9800
C1B—C6B	1.3888 (17)	C7D—H7DC	0.9800
C2B—C3B	1.4029 (17)	C8D—H8DA	0.9800
C2B—C7B	1.5110 (17)	C8D—H8DB	0.9800
C3B—C4B	1.389 (2)	C8D—H8DC	0.9800
C3B—C8B	1.5038 (19)	N1D—C10D	1.4881 (14)
C4B—H4B	0.9500	N1D—C11D	1.5036 (13)
C4B—C5B	1.379 (2)	N1D—H1DA	0.884 (18)
C5B—H5B	0.9500	N1D—H1DB	0.938 (16)
C5B—C6B	1.3874 (18)	O2D—C12D	1.4161 (14)
C6B—H6B	0.9500	O2D—H2D	0.92 (2)
C7B—H7BA	0.9800	C9D—H9DA	0.9900
C7B—H7BB	0.9800	C9D—H9DB	0.9900
C7B—H7BC	0.9800	C9D—C10D	1.5150 (16)
C8B—H8BA	0.9800	C10D—H10G	0.9900
C8B—H8BB	0.9800	C10D—H10H	0.9900
C8B—H8BC	0.9800	C11D—H11D	1.0000
N1B—C10B	1.4883 (14)	C11D—C12D	1.5277 (15)
N1B—C11B	1.5067 (13)	C11D—C16D	1.5309 (15)
N1B—H1BA	0.884 (17)	C12D—H12D	1.0000
N1B—H1BB	0.934 (17)	C12D—C13D	1.5319 (17)
O2B—C12B	1.4166 (13)	C13D—H13G	0.9900
O2B—H2B	0.94 (2)	C13D—H13H	0.9900
C9B—C10B	1.5142 (16)	C13D—C14D	1.5250 (18)
C9B—H9BA	0.957 (15)	C14D—H14G	0.9900
C9B—H9BB	0.968 (15)	C14D—H14H	0.9900
C10B—H10C	0.9900	C14D—C15D	1.5273 (19)
C10B—H10D	0.9900	C15D—H15G	0.9900
C11B—H11B	1.0000	C15D—H15H	0.9900
C11B—C12B	1.5310 (15)	C15D—C16D	1.5271 (17)
C11B—C16B	1.5305 (14)	C16D—H16G	0.9900
C12B—H12B	1.0000	C16D—H16H	0.9900
C12B—C13B	1.5331 (16)	O3A—C21A	1.2423 (14)
C13B—H13C	0.9900	O4A—C21A	1.2720 (13)
C13B—H13D	0.9900	O5A—C24A	1.2721 (13)
C13B—C14B	1.5284 (18)	O6A—C24A	1.2435 (14)
C14B—H14C	0.9900	C21A—C22A	1.5231 (14)
C14B—H14D	0.9900	C22A—H22A	0.9900
C14B—C15B	1.5276 (19)	C22A—H22B	0.9900
C15B—H15C	0.9900	C22A—C23A	1.5178 (16)
C15B—H15D	0.9900	C23A—H23A	0.9900
C15B—C16B	1.5289 (17)	C23A—H23B	0.9900
C16B—H16C	0.9900	C23A—C24A	1.5216 (14)
C16B—H16D	0.9900	O3B—C21B	1.2707 (13)
O1C—C1C	1.3729 (14)	O4B—C21B	1.2428 (14)
O1C—C9C	1.4211 (13)	C21B—C22B	1.5214 (14)
C1C—C2C	1.4025 (16)	C22B—C22B^i	1.516 (2)
C1C—C6C	1.3939 (17)	C22B—H22C	0.9900
C2C—C3C	1.3940 (17)	C22B—H22D	0.9900
C2C—C7C	1.5055 (17)	O3C—C21C	1.2725 (13)
C3C—C4C	1.403 (2)	O4C—C21C	1.2429 (14)
C3C—C8C	1.5018 (18)	C21C—C22C	1.5233 (14)
C4C—H4C	0.9500	C22C—C22C^ii	1.5171 (19)
C4C—C5C	1.3805 (19)	C22C—H22E	0.9900
C5C—H5C	0.9500	C22C—H22F	0.9900
C5C—C6C	1.3911 (17)
C1A—O1A—C9A	117.96 (9)	C5C—C6C—H6C	120.4
O1A—C1A—C2A	115.51 (10)	C2C—C7C—H7CA	109.5
O1A—C1A—C6A	123.23 (11)	C2C—C7C—H7CB	109.5
C6A—C1A—C2A	121.26 (11)	C2C—C7C—H7CC	109.5
C1A—C2A—C7A	119.95 (11)	H7CA—C7C—H7CB	109.5
C3A—C2A—C1A	119.10 (11)	H7CA—C7C—H7CC	109.5
C3A—C2A—C7A	120.90 (11)	H7CB—C7C—H7CC	109.5
C2A—C3A—C4A	119.41 (12)	C3C—C8C—H8CA	109.5
C2A—C3A—C8A	120.62 (13)	C3C—C8C—H8CB	109.5
C4A—C3A—C8A	119.97 (12)	C3C—C8C—H8CC	109.5
C3A—C4A—H4A	119.6	H8CA—C8C—H8CB	109.5
C5A—C4A—C3A	120.76 (12)	H8CA—C8C—H8CC	109.5
C5A—C4A—H4A	119.6	H8CB—C8C—H8CC	109.5
C4A—C5A—H5A	119.8	C10C—N1C—C11C	114.07 (8)
C4A—C5A—C6A	120.49 (12)	C10C—N1C—H1CA	106.0 (10)
C6A—C5A—H5A	119.8	C10C—N1C—H1CB	108.5 (10)
C1A—C6A—H6A	120.5	C11C—N1C—H1CA	110.0 (10)
C5A—C6A—C1A	118.97 (11)	C11C—N1C—H1CB	110.8 (10)
C5A—C6A—H6A	120.5	H1CA—N1C—H1CB	107.1 (14)
C2A—C7A—H7AA	109.5	C12C—O2C—H2C	110.8 (12)
C2A—C7A—H7AB	109.5	O1C—C9C—C10C	105.33 (9)
C2A—C7A—H7AC	109.5	O1C—C9C—H9CA	108.4 (9)
H7AA—C7A—H7AB	109.5	O1C—C9C—H9CB	111.1 (8)
H7AA—C7A—H7AC	109.5	C10C—C9C—H9CA	110.1 (9)
H7AB—C7A—H7AC	109.5	C10C—C9C—H9CB	110.5 (8)
C3A—C8A—H8AA	109.5	H9CA—C9C—H9CB	111.2 (12)
C3A—C8A—H8AB	109.5	N1C—C10C—C9C	109.16 (9)
C3A—C8A—H8AC	109.5	N1C—C10C—H10E	109.8
H8AA—C8A—H8AB	109.5	N1C—C10C—H10F	109.8
H8AA—C8A—H8AC	109.5	C9C—C10C—H10E	109.8
H8AB—C8A—H8AC	109.5	C9C—C10C—H10F	109.8
C10A—N1A—C11A	113.66 (8)	H10E—C10C—H10F	108.3
C10A—N1A—H1AA	105.7 (10)	N1C—C11C—H11C	108.9
C10A—N1A—H1AB	109.2 (10)	N1C—C11C—C12C	109.59 (9)
C11A—N1A—H1AA	111.0 (10)	N1C—C11C—C16C	109.44 (9)
C11A—N1A—H1AB	111.1 (10)	C12C—C11C—H11C	108.9
H1AA—N1A—H1AB	105.9 (14)	C12C—C11C—C16C	111.17 (9)
C12A—O2A—H2A	110.3 (13)	C16C—C11C—H11C	108.9
O1A—C9A—C10A	104.95 (9)	O2C—C12C—C11C	111.94 (9)
O1A—C9A—H9AA	112.1 (9)	O2C—C12C—H12C	107.7
O1A—C9A—H9AB	108.4 (9)	O2C—C12C—C13C	111.61 (9)
C10A—C9A—H9AA	110.4 (9)	C11C—C12C—H12C	107.7
C10A—C9A—H9AB	110.4 (9)	C11C—C12C—C13C	109.94 (9)
H9AA—C9A—H9AB	110.5 (12)	C13C—C12C—H12C	107.7
N1A—C10A—C9A	109.79 (9)	C12C—C13C—H13E	109.1
N1A—C10A—H10A	109.7	C12C—C13C—H13F	109.1
N1A—C10A—H10B	109.7	H13E—C13C—H13F	107.8
C9A—C10A—H10A	109.7	C14C—C13C—C12C	112.47 (10)
C9A—C10A—H10B	109.7	C14C—C13C—H13E	109.1
H10A—C10A—H10B	108.2	C14C—C13C—H13F	109.1
N1A—C11A—H11A	108.8	C13C—C14C—H14E	109.6
N1A—C11A—C12A	110.02 (9)	C13C—C14C—H14F	109.6
N1A—C11A—C16A	109.58 (9)	C13C—C14C—C15C	110.46 (10)
C12A—C11A—H11A	108.8	H14E—C14C—H14F	108.1
C12A—C11A—C16A	110.73 (9)	C15C—C14C—H14E	109.6
C16A—C11A—H11A	108.8	C15C—C14C—H14F	109.6
O2A—C12A—C11A	111.80 (9)	C14C—C15C—H15E	109.4
O2A—C12A—H12A	107.8	C14C—C15C—H15F	109.4
O2A—C12A—C13A	111.95 (9)	H15E—C15C—H15F	108.0
C11A—C12A—H12A	107.8	C16C—C15C—C14C	111.07 (11)
C11A—C12A—C13A	109.54 (9)	C16C—C15C—H15E	109.4
C13A—C12A—H12A	107.8	C16C—C15C—H15F	109.4
C12A—C13A—H13A	109.1	C11C—C16C—H16E	109.5
C12A—C13A—H13B	109.1	C11C—C16C—H16F	109.5
H13A—C13A—H13B	107.9	C15C—C16C—C11C	110.63 (10)
C14A—C13A—C12A	112.30 (10)	C15C—C16C—H16E	109.5
C14A—C13A—H13A	109.1	C15C—C16C—H16F	109.5
C14A—C13A—H13B	109.1	H16E—C16C—H16F	108.1
C13A—C14A—H14A	109.5	C1D—O1D—C9D	117.38 (9)
C13A—C14A—H14B	109.5	O1D—C1D—C2D	115.09 (11)
H14A—C14A—H14B	108.1	O1D—C1D—C6D	123.15 (11)
C15A—C14A—C13A	110.72 (10)	C6D—C1D—C2D	121.73 (12)
C15A—C14A—H14A	109.5	C1D—C2D—C7D	119.50 (11)
C15A—C14A—H14B	109.5	C3D—C2D—C1D	118.41 (12)
C14A—C15A—H15A	109.5	C3D—C2D—C7D	122.02 (11)
C14A—C15A—H15B	109.5	C2D—C3D—C8D	120.60 (12)
H15A—C15A—H15B	108.1	C4D—C3D—C2D	119.67 (12)
C16A—C15A—C14A	110.89 (11)	C4D—C3D—C8D	119.64 (12)
C16A—C15A—H15A	109.5	C3D—C4D—H4D	119.6
C16A—C15A—H15B	109.5	C5D—C4D—C3D	120.78 (12)
C11A—C16A—H16A	109.5	C5D—C4D—H4D	119.6
C11A—C16A—H16B	109.5	C4D—C5D—H5D	119.6
C15A—C16A—C11A	110.53 (10)	C4D—C5D—C6D	120.75 (12)
C15A—C16A—H16A	109.5	C6D—C5D—H5D	119.6
C15A—C16A—H16B	109.5	C1D—C6D—H6D	120.7
H16A—C16A—H16B	108.1	C5D—C6D—C1D	118.63 (12)
C1B—O1B—C9B	117.60 (9)	C5D—C6D—H6D	120.7
O1B—C1B—C2B	115.27 (10)	C2D—C7D—H7DA	109.5
O1B—C1B—C6B	123.07 (11)	C2D—C7D—H7DB	109.5
C6B—C1B—C2B	121.62 (11)	C2D—C7D—H7DC	109.5
C1B—C2B—C3B	118.66 (11)	H7DA—C7D—H7DB	109.5
C1B—C2B—C7B	119.26 (11)	H7DA—C7D—H7DC	109.5
C3B—C2B—C7B	122.03 (11)	H7DB—C7D—H7DC	109.5
C2B—C3B—C8B	120.79 (12)	C3D—C8D—H8DA	109.5
C4B—C3B—C2B	119.38 (12)	C3D—C8D—H8DB	109.5
C4B—C3B—C8B	119.72 (12)	C3D—C8D—H8DC	109.5
C3B—C4B—H4B	119.5	H8DA—C8D—H8DB	109.5
C5B—C4B—C3B	121.06 (12)	H8DA—C8D—H8DC	109.5
C5B—C4B—H4B	119.5	H8DB—C8D—H8DC	109.5
C4B—C5B—H5B	119.7	C10D—N1D—C11D	114.47 (8)
C4B—C5B—C6B	120.58 (12)	C10D—N1D—H1DA	106.1 (10)
C6B—C5B—H5B	119.7	C10D—N1D—H1DB	107.0 (9)
C1B—C6B—H6B	120.7	C11D—N1D—H1DA	111.2 (10)
C5B—C6B—C1B	118.69 (12)	C11D—N1D—H1DB	109.9 (9)
C5B—C6B—H6B	120.7	H1DA—N1D—H1DB	107.8 (14)
C2B—C7B—H7BA	109.5	C12D—O2D—H2D	109.9 (12)
C2B—C7B—H7BB	109.5	O1D—C9D—H9DA	110.7
C2B—C7B—H7BC	109.5	O1D—C9D—H9DB	110.7
H7BA—C7B—H7BB	109.5	O1D—C9D—C10D	105.14 (9)
H7BA—C7B—H7BC	109.5	H9DA—C9D—H9DB	108.8
H7BB—C7B—H7BC	109.5	C10D—C9D—H9DA	110.7
C3B—C8B—H8BA	109.5	C10D—C9D—H9DB	110.7
C3B—C8B—H8BB	109.5	N1D—C10D—C9D	109.57 (9)
C3B—C8B—H8BC	109.5	N1D—C10D—H10G	109.8
H8BA—C8B—H8BB	109.5	N1D—C10D—H10H	109.8
H8BA—C8B—H8BC	109.5	C9D—C10D—H10G	109.8
H8BB—C8B—H8BC	109.5	C9D—C10D—H10H	109.8
C10B—N1B—C11B	114.43 (8)	H10G—C10D—H10H	108.2
C10B—N1B—H1BA	107.9 (10)	N1D—C11D—H11D	108.8
C10B—N1B—H1BB	105.5 (10)	N1D—C11D—C12D	110.39 (9)
C11B—N1B—H1BA	109.9 (10)	N1D—C11D—C16D	108.98 (9)
C11B—N1B—H1BB	110.2 (10)	C12D—C11D—H11D	108.8
H1BA—N1B—H1BB	108.7 (14)	C12D—C11D—C16D	110.89 (9)
C12B—O2B—H2B	110.9 (12)	C16D—C11D—H11D	108.8
O1B—C9B—C10B	104.91 (9)	O2D—C12D—C11D	112.20 (9)
O1B—C9B—H9BA	111.9 (8)	O2D—C12D—H12D	107.7
O1B—C9B—H9BB	109.6 (8)	O2D—C12D—C13D	111.18 (9)
C10B—C9B—H9BA	111.3 (9)	C11D—C12D—H12D	107.7
C10B—C9B—H9BB	110.9 (9)	C11D—C12D—C13D	110.06 (10)
H9BA—C9B—H9BB	108.2 (12)	C13D—C12D—H12D	107.7
N1B—C10B—C9B	110.08 (9)	C12D—C13D—H13G	109.1
N1B—C10B—H10C	109.6	C12D—C13D—H13H	109.1
N1B—C10B—H10D	109.6	H13G—C13D—H13H	107.8
C9B—C10B—H10C	109.6	C14D—C13D—C12D	112.57 (10)
C9B—C10B—H10D	109.6	C14D—C13D—H13G	109.1
H10C—C10B—H10D	108.2	C14D—C13D—H13H	109.1
N1B—C11B—H11B	108.9	C13D—C14D—H14G	109.5
N1B—C11B—C12B	110.61 (9)	C13D—C14D—H14H	109.5
N1B—C11B—C16B	109.12 (9)	C13D—C14D—C15D	110.55 (11)
C12B—C11B—H11B	108.9	H14G—C14D—H14H	108.1
C16B—C11B—H11B	108.9	C15D—C14D—H14G	109.5
C16B—C11B—C12B	110.47 (9)	C15D—C14D—H14H	109.5
O2B—C12B—C11B	112.14 (9)	C14D—C15D—H15G	109.4
O2B—C12B—H12B	107.8	C14D—C15D—H15H	109.4
O2B—C12B—C13B	111.64 (9)	H15G—C15D—H15H	108.0
C11B—C12B—H12B	107.8	C16D—C15D—C14D	111.15 (11)
C11B—C12B—C13B	109.49 (9)	C16D—C15D—H15G	109.4
C13B—C12B—H12B	107.8	C16D—C15D—H15H	109.4
C12B—C13B—H13C	109.1	C11D—C16D—H16G	109.5
C12B—C13B—H13D	109.1	C11D—C16D—H16H	109.5
H13C—C13B—H13D	107.9	C15D—C16D—C11D	110.83 (10)
C14B—C13B—C12B	112.28 (10)	C15D—C16D—H16G	109.5
C14B—C13B—H13C	109.1	C15D—C16D—H16H	109.5
C14B—C13B—H13D	109.1	H16G—C16D—H16H	108.1
C13B—C14B—H14C	109.5	O3A—C21A—O4A	123.24 (10)
C13B—C14B—H14D	109.5	O3A—C21A—C22A	120.14 (9)
H14C—C14B—H14D	108.1	O4A—C21A—C22A	116.62 (9)
C15B—C14B—C13B	110.75 (11)	C21A—C22A—H22A	108.7
C15B—C14B—H14C	109.5	C21A—C22A—H22B	108.7
C15B—C14B—H14D	109.5	H22A—C22A—H22B	107.6
C14B—C15B—H15C	109.5	C23A—C22A—C21A	114.25 (10)
C14B—C15B—H15D	109.5	C23A—C22A—H22A	108.7
C14B—C15B—C16B	110.76 (11)	C23A—C22A—H22B	108.7
H15C—C15B—H15D	108.1	C22A—C23A—H23A	108.6
C16B—C15B—H15C	109.5	C22A—C23A—H23B	108.6
C16B—C15B—H15D	109.5	C22A—C23A—C24A	114.54 (10)
C11B—C16B—H16C	109.5	H23A—C23A—H23B	107.6
C11B—C16B—H16D	109.5	C24A—C23A—H23A	108.6
C15B—C16B—C11B	110.70 (10)	C24A—C23A—H23B	108.6
C15B—C16B—H16C	109.5	O5A—C24A—C23A	116.50 (9)
C15B—C16B—H16D	109.5	O6A—C24A—O5A	123.37 (10)
H16C—C16B—H16D	108.1	O6A—C24A—C23A	120.12 (9)
C1C—O1C—C9C	117.60 (9)	O3B—C21B—C22B	116.51 (9)
O1C—C1C—C2C	115.37 (10)	O4B—C21B—O3B	123.33 (10)
O1C—C1C—C6C	123.39 (11)	O4B—C21B—C22B	120.15 (9)
C6C—C1C—C2C	121.24 (11)	C21B—C22B—H22C	108.7
C1C—C2C—C7C	120.08 (11)	C21B—C22B—H22D	108.7
C3C—C2C—C1C	118.92 (11)	C22B^i—C22B—C21B	114.34 (11)
C3C—C2C—C7C	120.97 (11)	C22B^i—C22B—H22C	108.7
C2C—C3C—C4C	119.64 (12)	C22B^i—C22B—H22D	108.7
C2C—C3C—C8C	120.46 (13)	H22C—C22B—H22D	107.6
C4C—C3C—C8C	119.90 (12)	O3C—C21C—C22C	116.66 (9)
C3C—C4C—H4C	119.6	O4C—C21C—O3C	123.33 (10)
C5C—C4C—C3C	120.80 (12)	O4C—C21C—C22C	120.00 (9)
C5C—C4C—H4C	119.6	C21C—C22C—H22E	108.7
C4C—C5C—H5C	119.9	C21C—C22C—H22F	108.7
C4C—C5C—C6C	120.26 (12)	C22C^ii—C22C—C21C	114.43 (11)
C6C—C5C—H5C	119.9	C22C^ii—C22C—H22E	108.7
C1C—C6C—H6C	120.4	C22C^ii—C22C—H22F	108.7
C5C—C6C—C1C	119.15 (11)	H22E—C22C—H22F	107.6
O1A—C1A—C2A—C3A	179.31 (10)	C1C—C2C—C3C—C4C	−0.16 (18)
O1A—C1A—C2A—C7A	−3.17 (16)	C1C—C2C—C3C—C8C	179.50 (12)
O1A—C1A—C6A—C5A	−179.11 (11)	C2C—C1C—C6C—C5C	0.88 (18)
O1A—C9A—C10A—N1A	172.98 (9)	C2C—C3C—C4C—C5C	0.86 (19)
C1A—O1A—C9A—C10A	175.04 (9)	C3C—C4C—C5C—C6C	−0.7 (2)
C1A—C2A—C3A—C4A	−0.47 (18)	C4C—C5C—C6C—C1C	−0.17 (19)
C1A—C2A—C3A—C8A	179.87 (11)	C6C—C1C—C2C—C3C	−0.71 (18)
C2A—C1A—C6A—C5A	0.50 (18)	C6C—C1C—C2C—C7C	177.51 (11)
C2A—C3A—C4A—C5A	1.11 (19)	C7C—C2C—C3C—C4C	−178.36 (11)
C3A—C4A—C5A—C6A	−0.9 (2)	C7C—C2C—C3C—C8C	1.30 (19)
C4A—C5A—C6A—C1A	0.13 (19)	C8C—C3C—C4C—C5C	−178.80 (12)
C6A—C1A—C2A—C3A	−0.32 (18)	N1C—C11C—C12C—O2C	57.83 (11)
C6A—C1A—C2A—C7A	177.19 (11)	N1C—C11C—C12C—C13C	−177.53 (9)
C7A—C2A—C3A—C4A	−177.96 (11)	N1C—C11C—C16C—C15C	179.00 (10)
C7A—C2A—C3A—C8A	2.38 (19)	O2C—C12C—C13C—C14C	−179.66 (10)
C8A—C3A—C4A—C5A	−179.24 (12)	C9C—O1C—C1C—C2C	179.00 (10)
N1A—C11A—C12A—O2A	56.55 (11)	C9C—O1C—C1C—C6C	−0.92 (17)
N1A—C11A—C12A—C13A	−178.76 (9)	C10C—N1C—C11C—C12C	−92.35 (11)
N1A—C11A—C16A—C15A	−179.64 (9)	C10C—N1C—C11C—C16C	145.50 (10)
O2A—C12A—C13A—C14A	−179.39 (10)	C11C—N1C—C10C—C9C	176.18 (9)
C9A—O1A—C1A—C2A	178.74 (10)	C11C—C12C—C13C—C14C	55.50 (14)
C9A—O1A—C1A—C6A	−1.64 (17)	C12C—C11C—C16C—C15C	57.80 (13)
C10A—N1A—C11A—C12A	−92.16 (11)	C12C—C13C—C14C—C15C	−55.03 (15)
C10A—N1A—C11A—C16A	145.88 (9)	C13C—C14C—C15C—C16C	55.23 (15)
C11A—N1A—C10A—C9A	178.11 (9)	C14C—C15C—C16C—C11C	−56.96 (14)
C11A—C12A—C13A—C14A	56.01 (13)	C16C—C11C—C12C—O2C	178.93 (9)
C12A—C11A—C16A—C15A	58.82 (13)	C16C—C11C—C12C—C13C	−56.42 (12)
C12A—C13A—C14A—C15A	−55.05 (15)	O1D—C1D—C2D—C3D	−175.80 (11)
C13A—C14A—C15A—C16A	55.00 (15)	O1D—C1D—C2D—C7D	1.43 (18)
C14A—C15A—C16A—C11A	−57.25 (14)	O1D—C1D—C6D—C5D	176.04 (12)
C16A—C11A—C12A—O2A	177.83 (9)	O1D—C9D—C10D—N1D	−172.05 (9)
C16A—C11A—C12A—C13A	−57.48 (12)	C1D—O1D—C9D—C10D	−170.26 (10)
O1B—C1B—C2B—C3B	−176.49 (11)	C1D—C2D—C3D—C4D	−1.15 (19)
O1B—C1B—C2B—C7B	1.14 (17)	C1D—C2D—C3D—C8D	175.35 (12)
O1B—C1B—C6B—C5B	176.46 (12)	C2D—C1D—C6D—C5D	−1.77 (19)
O1B—C9B—C10B—N1B	−173.79 (9)	C2D—C3D—C4D—C5D	−0.2 (2)
C1B—O1B—C9B—C10B	−169.41 (10)	C3D—C4D—C5D—C6D	0.7 (2)
C1B—C2B—C3B—C4B	−0.54 (19)	C4D—C5D—C6D—C1D	0.3 (2)
C1B—C2B—C3B—C8B	175.62 (12)	C6D—C1D—C2D—C3D	2.18 (19)
C2B—C1B—C6B—C5B	−0.90 (19)	C6D—C1D—C2D—C7D	179.41 (12)
C2B—C3B—C4B—C5B	−0.1 (2)	C7D—C2D—C3D—C4D	−178.30 (13)
C3B—C4B—C5B—C6B	0.3 (2)	C7D—C2D—C3D—C8D	−1.8 (2)
C4B—C5B—C6B—C1B	0.2 (2)	C8D—C3D—C4D—C5D	−176.77 (13)
C6B—C1B—C2B—C3B	1.06 (19)	N1D—C11D—C12D—O2D	58.67 (12)
C6B—C1B—C2B—C7B	178.69 (12)	N1D—C11D—C12D—C13D	−176.97 (9)
C7B—C2B—C3B—C4B	−178.10 (13)	N1D—C11D—C16D—C15D	179.21 (10)
C7B—C2B—C3B—C8B	−1.9 (2)	O2D—C12D—C13D—C14D	−179.59 (10)
C8B—C3B—C4B—C5B	−176.32 (13)	C9D—O1D—C1D—C2D	174.54 (11)
N1B—C11B—C12B—O2B	57.06 (11)	C9D—O1D—C1D—C6D	−3.41 (18)
N1B—C11B—C12B—C13B	−178.44 (9)	C10D—N1D—C11D—C12D	−85.08 (11)
N1B—C11B—C16B—C15B	−179.35 (10)	C10D—N1D—C11D—C16D	152.91 (10)
O2B—C12B—C13B—C14B	−178.92 (10)	C11D—N1D—C10D—C9D	−172.57 (9)
C9B—O1B—C1B—C2B	174.10 (11)	C11D—C12D—C13D—C14D	55.46 (14)
C9B—O1B—C1B—C6B	−3.41 (18)	C12D—C11D—C16D—C15D	57.50 (13)
C10B—N1B—C11B—C12B	−84.32 (11)	C12D—C13D—C14D—C15D	−54.98 (15)
C10B—N1B—C11B—C16B	153.96 (9)	C13D—C14D—C15D—C16D	55.14 (15)
C11B—N1B—C10B—C9B	−170.18 (9)	C14D—C15D—C16D—C11D	−56.88 (15)
C11B—C12B—C13B—C14B	56.29 (13)	C16D—C11D—C12D—O2D	179.55 (9)
C12B—C11B—C16B—C15B	58.85 (13)	C16D—C11D—C12D—C13D	−56.09 (12)
C12B—C13B—C14B—C15B	−55.30 (16)	O3A—C21A—C22A—C23A	14.36 (16)
C13B—C14B—C15B—C16B	55.06 (16)	O4A—C21A—C22A—C23A	−166.10 (10)
C14B—C15B—C16B—C11B	−57.30 (14)	C21A—C22A—C23A—C24A	179.41 (8)
C16B—C11B—C12B—O2B	177.98 (9)	C22A—C23A—C24A—O5A	167.26 (10)
C16B—C11B—C12B—C13B	−57.52 (12)	C22A—C23A—C24A—O6A	−13.84 (16)
O1C—C1C—C2C—C3C	179.37 (10)	O3B—C21B—C22B—C22B^i	168.31 (12)
O1C—C1C—C2C—C7C	−2.41 (16)	O4B—C21B—C22B—C22B^i	−12.50 (18)
O1C—C1C—C6C—C5C	−179.21 (11)	O3C—C21C—C22C—C22C^ii	−164.73 (11)
O1C—C9C—C10C—N1C	173.82 (9)	O4C—C21C—C22C—C22C^ii	16.14 (18)
C1C—O1C—C9C—C10C	174.54 (9)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AA···O4B^i	0.907 (17)	1.885 (17)	2.7693 (12)	164.6 (14)
N1A—H1AB···O3C^iii	0.854 (18)	1.904 (18)	2.7554 (13)	174.6 (15)
N1A—H1AB···O4C^iii	0.854 (18)	2.577 (16)	3.1001 (12)	120.6 (13)
O2A—H2A···O4A^iv	0.91 (2)	1.79 (2)	2.6997 (11)	179 (2)
N1B—H1BA···O3A^iv	0.884 (17)	2.558 (16)	3.1375 (12)	123.9 (12)
N1B—H1BA···O4A^iv	0.884 (17)	1.861 (17)	2.7359 (13)	170.2 (14)
N1B—H1BB···O3A	0.934 (17)	1.855 (17)	2.7851 (12)	173.4 (14)
O2B—H2B···O3B	0.94 (2)	1.77 (2)	2.7023 (11)	177 (2)
N1C—H1CA···O6A^v	0.898 (17)	1.899 (17)	2.7786 (12)	165.7 (15)
N1C—H1CB···O5A^vi	0.859 (18)	1.888 (18)	2.7447 (13)	175.5 (15)
N1C—H1CB···O6A^vi	0.859 (18)	2.551 (16)	3.0868 (12)	121.4 (13)
O2C—H2C···O3C^ii	0.90 (2)	1.80 (2)	2.7011 (11)	179 (2)
N1D—H1DA···O3B^vi	0.884 (18)	1.844 (18)	2.7222 (13)	172.1 (15)
N1D—H1DA···O4B^vi	0.884 (18)	2.531 (16)	3.1283 (12)	125.5 (13)
N1D—H1DB···O4C	0.938 (16)	1.860 (16)	2.7918 (12)	172.4 (14)
O2D—H2D···O5A^vi	0.92 (2)	1.79 (2)	2.7060 (11)	176.6 (19)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x+1, −y+1, −z+1; (v) x+1/2, −y+3/2, z−1/2; (vi) −x+3/2, y−1/2, −z+1/2.

D,L-trans-N-[(2,3-Dimethylphenoxy)ethyl]-1-hydroxycyclohexan-2-aminium 6-carboxy-pyridine-2-carboxylate (2)

Crystal data

C16H25NO2^+·C7H4NO4^−	F(000) = 916
Mr = 429.48	Dx = 1.316 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 9.7442 (1) Å	Cell parameters from 46770 reflections
b = 13.1462 (1) Å	θ = 2.6–76.4°
c = 17.0714 (1) Å	µ = 0.79 mm^−1
β = 97.662 (1)°	T = 100 K
V = 2167.31 (3) Å^3	Prism, clear colourless
Z = 4	0.39 × 0.34 × 0.16 mm

Data collection

Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector	4496 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	4365 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.037
Detector resolution: 10.0000 pixels mm^-1	θmax = 76.6°, θmin = 4.6°
ω scans	h = −12→12
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2023)	k = −14→16
Tmin = 0.426, Tmax = 1.000	l = −21→21
71713 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[σ^2(Fo^2) + (0.0368P)^2 + 1.1438P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.094	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.31 e Å^−3
4496 reflections	Δρmin = −0.20 e Å^−3
322 parameters	Extinction correction: SHELXL2019 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
15 restraints	Extinction coefficient: 0.00199 (15)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.23172 (9)	0.08577 (6)	0.72928 (5)	0.02192 (19)
O3	0.51356 (10)	0.22948 (7)	0.81260 (5)	0.0267 (2)
O4B	0.5402 (15)	0.2865 (8)	0.9362 (5)	0.057 (2)	0.54 (5)
O5	0.57048 (9)	−0.11366 (7)	0.75775 (5)	0.0228 (2)
O6	0.61557 (11)	−0.22788 (7)	0.85517 (5)	0.0307 (2)
N1	0.51080 (11)	0.07877 (8)	0.68285 (6)	0.0207 (2)
N2	0.58823 (10)	0.04027 (8)	0.86253 (6)	0.0193 (2)
C1	0.14255 (12)	0.06748 (9)	0.78388 (7)	0.0194 (2)
C2	0.10630 (12)	0.15337 (9)	0.82538 (7)	0.0210 (2)
C3	0.01652 (13)	0.14069 (10)	0.88226 (7)	0.0245 (3)
C4	−0.03572 (13)	0.04436 (11)	0.89561 (8)	0.0260 (3)
H4	−0.096553	0.036028	0.934237	0.031*
C5	−0.00027 (13)	−0.03901 (10)	0.85347 (7)	0.0245 (3)
H5	−0.037723	−0.103927	0.862813	0.029*
C6	0.09035 (12)	−0.02842 (9)	0.79721 (7)	0.0220 (3)
H6	0.115891	−0.085773	0.768537	0.026*
C7	0.16442 (14)	0.25631 (10)	0.80953 (8)	0.0269 (3)
H7A	0.090345	0.307194	0.805929	0.040*
H7B	0.203777	0.254396	0.759632	0.040*
H7C	0.236967	0.274354	0.852707	0.040*
C8	−0.02333 (16)	0.23050 (12)	0.92938 (10)	0.0382 (4)
H8A	0.060531	0.263678	0.955565	0.057*
H8B	−0.079740	0.207127	0.969280	0.057*
H8C	−0.076673	0.279054	0.893903	0.057*
C9	0.28099 (13)	−0.00037 (9)	0.69075 (7)	0.0233 (3)
H9A	0.202538	−0.035817	0.659313	0.028*
H9B	0.326718	−0.048587	0.730489	0.028*
C10	0.38263 (13)	0.03524 (10)	0.63741 (7)	0.0237 (3)
H10A	0.408122	−0.022801	0.605329	0.028*
H10B	0.337992	0.087521	0.600783	0.028*
C11	0.62563 (12)	0.10271 (9)	0.63405 (7)	0.0197 (2)
H11	0.588588	0.149389	0.590006	0.024*
C12	0.74309 (14)	0.15704 (10)	0.68686 (8)	0.0278 (3)
H12	0.776695	0.111534	0.732332	0.033*
C13	0.86399 (14)	0.17963 (12)	0.64104 (8)	0.0339 (3)
H13A	0.833823	0.229415	0.598713	0.041*
H13B	0.940351	0.210802	0.677196	0.041*
C14	0.91696 (14)	0.08492 (13)	0.60455 (9)	0.0368 (4)
H14A	0.957215	0.037996	0.646847	0.044*
H14B	0.990635	0.103558	0.572477	0.044*
C15	0.79971 (14)	0.03238 (11)	0.55277 (8)	0.0305 (3)
H15A	0.834829	−0.030851	0.530994	0.037*
H15B	0.765405	0.077314	0.507860	0.037*
C16	0.68035 (13)	0.00637 (10)	0.59877 (7)	0.0237 (3)
H16	0.714383	−0.041599	0.642546	0.028*
O2A	0.71425 (17)	0.24974 (12)	0.71559 (10)	0.0267 (4)	0.600 (3)
O2B	0.5894 (3)	−0.0428 (2)	0.54527 (14)	0.0320 (7)	0.400 (3)
H2B	0.573 (5)	−0.096 (2)	0.568 (2)	0.048*	0.400 (3)
C19	0.59835 (12)	0.11606 (9)	0.91561 (7)	0.0207 (2)
C20	0.64490 (12)	0.10172 (10)	0.99569 (7)	0.0224 (3)
H20	0.650468	0.157443	1.031409	0.027*
C21	0.68284 (12)	0.00496 (10)	1.02226 (7)	0.0226 (3)
H21	0.716606	−0.006734	1.076318	0.027*
C22	0.67062 (12)	−0.07436 (10)	0.96857 (7)	0.0215 (2)
H22	0.694138	−0.141841	0.985168	0.026*
C23	0.62314 (12)	−0.05327 (9)	0.88968 (7)	0.0195 (2)
C24	0.55222 (14)	0.22135 (10)	0.88688 (8)	0.0270 (3)
C25	0.60305 (12)	−0.14001 (9)	0.83161 (7)	0.0219 (3)
H1A	0.5441 (18)	0.0327 (14)	0.7249 (10)	0.039 (5)*
H1B	0.4855 (19)	0.1393 (15)	0.7051 (11)	0.045 (5)*
H5A	0.541 (3)	−0.1727 (15)	0.7267 (13)	0.087 (8)*
H2A	0.670 (4)	0.235 (3)	0.743 (2)	0.043 (10)*	0.600 (3)
O4A	0.569 (2)	0.2944 (7)	0.9308 (8)	0.069 (3)	0.46 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0251 (4)	0.0195 (4)	0.0224 (4)	−0.0003 (3)	0.0079 (3)	−0.0011 (3)
O3	0.0338 (5)	0.0236 (5)	0.0218 (4)	0.0054 (4)	0.0008 (4)	0.0014 (3)
O4B	0.100 (4)	0.042 (4)	0.022 (2)	0.046 (3)	−0.010 (2)	−0.013 (2)
O5	0.0293 (5)	0.0193 (4)	0.0193 (4)	0.0003 (3)	0.0009 (3)	−0.0002 (3)
O6	0.0441 (6)	0.0191 (5)	0.0269 (5)	−0.0015 (4)	−0.0029 (4)	0.0031 (4)
N1	0.0237 (5)	0.0194 (5)	0.0189 (5)	−0.0016 (4)	0.0030 (4)	−0.0007 (4)
N2	0.0181 (5)	0.0206 (5)	0.0191 (5)	−0.0016 (4)	0.0021 (4)	0.0009 (4)
C1	0.0171 (5)	0.0228 (6)	0.0178 (5)	−0.0004 (4)	0.0000 (4)	0.0014 (4)
C2	0.0186 (5)	0.0213 (6)	0.0226 (6)	0.0001 (4)	0.0012 (4)	0.0000 (5)
C3	0.0209 (6)	0.0270 (7)	0.0258 (6)	0.0004 (5)	0.0039 (5)	−0.0025 (5)
C4	0.0215 (6)	0.0317 (7)	0.0254 (6)	−0.0020 (5)	0.0054 (5)	0.0014 (5)
C5	0.0218 (6)	0.0237 (6)	0.0274 (6)	−0.0042 (5)	0.0016 (5)	0.0031 (5)
C6	0.0222 (6)	0.0212 (6)	0.0219 (6)	−0.0012 (5)	0.0004 (5)	−0.0014 (5)
C7	0.0264 (6)	0.0206 (6)	0.0349 (7)	0.0002 (5)	0.0082 (5)	−0.0013 (5)
C8	0.0383 (8)	0.0347 (8)	0.0460 (9)	−0.0036 (6)	0.0214 (7)	−0.0098 (7)
C9	0.0232 (6)	0.0208 (6)	0.0261 (6)	−0.0014 (5)	0.0042 (5)	−0.0051 (5)
C10	0.0232 (6)	0.0268 (6)	0.0211 (6)	−0.0031 (5)	0.0024 (5)	−0.0055 (5)
C11	0.0217 (6)	0.0189 (6)	0.0187 (5)	−0.0012 (4)	0.0038 (4)	0.0018 (4)
C12	0.0357 (7)	0.0253 (7)	0.0215 (6)	−0.0098 (5)	0.0003 (5)	0.0001 (5)
C13	0.0285 (7)	0.0419 (8)	0.0289 (7)	−0.0146 (6)	−0.0047 (5)	0.0102 (6)
C14	0.0192 (6)	0.0536 (9)	0.0369 (8)	0.0002 (6)	0.0016 (5)	0.0176 (7)
C15	0.0257 (6)	0.0370 (8)	0.0299 (7)	0.0057 (6)	0.0085 (5)	0.0043 (6)
C16	0.0251 (6)	0.0218 (6)	0.0251 (6)	0.0002 (5)	0.0064 (5)	−0.0012 (5)
O2A	0.0292 (9)	0.0209 (8)	0.0320 (9)	−0.0060 (6)	0.0111 (7)	−0.0061 (6)
O2B	0.0331 (14)	0.0322 (14)	0.0325 (14)	−0.0100 (10)	0.0112 (10)	−0.0075 (10)
C19	0.0190 (5)	0.0220 (6)	0.0207 (6)	−0.0006 (4)	0.0016 (4)	−0.0007 (5)
C20	0.0199 (6)	0.0262 (6)	0.0207 (6)	−0.0015 (5)	0.0011 (4)	−0.0032 (5)
C21	0.0186 (5)	0.0299 (7)	0.0186 (5)	−0.0009 (5)	0.0008 (4)	0.0030 (5)
C22	0.0173 (5)	0.0242 (6)	0.0227 (6)	−0.0011 (4)	0.0016 (4)	0.0041 (5)
C23	0.0164 (5)	0.0207 (6)	0.0213 (6)	−0.0012 (4)	0.0026 (4)	0.0019 (5)
C24	0.0307 (7)	0.0248 (7)	0.0241 (6)	0.0012 (5)	−0.0020 (5)	−0.0006 (5)
C25	0.0213 (6)	0.0210 (6)	0.0229 (6)	−0.0011 (5)	0.0013 (4)	0.0015 (5)
O4A	0.122 (6)	0.021 (3)	0.051 (4)	−0.013 (4)	−0.037 (4)	−0.002 (2)

Geometric parameters (Å, º)

O1—C1	1.3773 (14)	C9—C10	1.5065 (17)
O1—C9	1.4248 (14)	C10—H10A	0.9900
O3—C24	1.2783 (15)	C10—H10B	0.9900
O4B—C24	1.218 (6)	C11—H11	1.0000
O5—C25	1.3053 (15)	C11—C12	1.5355 (17)
O5—H5A	0.962 (17)	C11—C16	1.5287 (17)
O6—C25	1.2239 (15)	C12—H12	1.0000
N1—C10	1.4935 (15)	C12—C13	1.5277 (19)
N1—C11	1.5144 (15)	C12—O2A	1.357 (2)
N1—H1A	0.962 (18)	C13—H13A	0.9900
N1—H1B	0.93 (2)	C13—H13B	0.9900
N2—C19	1.3415 (16)	C13—C14	1.513 (2)
N2—C23	1.3418 (16)	C14—H14A	0.9900
C1—C2	1.4029 (17)	C14—H14B	0.9900
C1—C6	1.3897 (17)	C14—C15	1.515 (2)
C2—C3	1.4010 (17)	C15—H15A	0.9900
C2—C7	1.5053 (17)	C15—H15B	0.9900
C3—C4	1.3949 (19)	C15—C16	1.5264 (17)
C3—C8	1.5084 (19)	C16—H16	1.0000
C4—H4	0.9500	C16—O2B	1.350 (3)
C4—C5	1.3798 (19)	O2A—H2A	0.71 (4)
C5—H5	0.9500	O2B—H2B	0.827 (19)
C5—C6	1.3956 (17)	C19—C20	1.3946 (17)
C6—H6	0.9500	C19—C24	1.5165 (18)
C7—H7A	0.9800	C20—H20	0.9500
C7—H7B	0.9800	C20—C21	1.3842 (18)
C7—H7C	0.9800	C21—H21	0.9500
C8—H8A	0.9800	C21—C22	1.3830 (18)
C8—H8B	0.9800	C22—H22	0.9500
C8—H8C	0.9800	C22—C23	1.3922 (16)
C9—H9A	0.9900	C23—C25	1.5066 (17)
C9—H9B	0.9900	C24—O4A	1.215 (9)
C1—O1—C9	117.10 (9)	C16—C11—C12	110.17 (10)
C25—O5—H5A	109.5 (15)	C11—C12—H12	108.6
C10—N1—C11	114.96 (9)	C13—C12—C11	110.81 (10)
C10—N1—H1A	108.8 (11)	C13—C12—H12	108.6
C10—N1—H1B	106.9 (12)	O2A—C12—C11	117.12 (13)
C11—N1—H1A	109.9 (10)	O2A—C12—H12	108.6
C11—N1—H1B	107.7 (12)	O2A—C12—C13	102.80 (12)
H1A—N1—H1B	108.3 (15)	C12—C13—H13A	109.1
C19—N2—C23	117.06 (10)	C12—C13—H13B	109.1
O1—C1—C2	115.16 (10)	H13A—C13—H13B	107.9
O1—C1—C6	123.16 (11)	C14—C13—C12	112.29 (12)
C6—C1—C2	121.68 (11)	C14—C13—H13A	109.1
C1—C2—C7	120.44 (11)	C14—C13—H13B	109.1
C3—C2—C1	118.48 (11)	C13—C14—H14A	109.6
C3—C2—C7	121.08 (11)	C13—C14—H14B	109.6
C2—C3—C8	120.36 (12)	C13—C14—C15	110.07 (11)
C4—C3—C2	119.77 (12)	H14A—C14—H14B	108.2
C4—C3—C8	119.87 (12)	C15—C14—H14A	109.6
C3—C4—H4	119.5	C15—C14—H14B	109.6
C5—C4—C3	120.91 (11)	C14—C15—H15A	109.3
C5—C4—H4	119.5	C14—C15—H15B	109.3
C4—C5—H5	119.8	C14—C15—C16	111.66 (11)
C4—C5—C6	120.33 (12)	H15A—C15—H15B	107.9
C6—C5—H5	119.8	C16—C15—H15A	109.3
C1—C6—C5	118.83 (11)	C16—C15—H15B	109.3
C1—C6—H6	120.6	C11—C16—H16	109.0
C5—C6—H6	120.6	C15—C16—C11	110.30 (11)
C2—C7—H7A	109.5	C15—C16—H16	109.0
C2—C7—H7B	109.5	O2B—C16—C11	115.54 (15)
C2—C7—H7C	109.5	O2B—C16—C15	103.65 (14)
H7A—C7—H7B	109.5	O2B—C16—H16	109.0
H7A—C7—H7C	109.5	C12—O2A—H2A	100 (3)
H7B—C7—H7C	109.5	C16—O2B—H2B	104 (3)
C3—C8—H8A	109.5	N2—C19—C20	123.15 (11)
C3—C8—H8B	109.5	N2—C19—C24	117.88 (10)
C3—C8—H8C	109.5	C20—C19—C24	118.95 (11)
H8A—C8—H8B	109.5	C19—C20—H20	120.6
H8A—C8—H8C	109.5	C21—C20—C19	118.89 (11)
H8B—C8—H8C	109.5	C21—C20—H20	120.6
O1—C9—H9A	109.9	C20—C21—H21	120.7
O1—C9—H9B	109.9	C22—C21—C20	118.69 (11)
O1—C9—C10	108.74 (10)	C22—C21—H21	120.7
H9A—C9—H9B	108.3	C21—C22—H22	120.7
C10—C9—H9A	109.9	C21—C22—C23	118.63 (11)
C10—C9—H9B	109.9	C23—C22—H22	120.7
N1—C10—C9	112.13 (10)	N2—C23—C22	123.56 (11)
N1—C10—H10A	109.2	N2—C23—C25	117.49 (10)
N1—C10—H10B	109.2	C22—C23—C25	118.89 (11)
C9—C10—H10A	109.2	O3—C24—C19	115.63 (11)
C9—C10—H10B	109.2	O4B—C24—O3	125.8 (4)
H10A—C10—H10B	107.9	O4B—C24—C19	118.0 (4)
N1—C11—H11	108.8	O4A—C24—O3	122.9 (6)
N1—C11—C12	108.74 (9)	O4A—C24—C19	120.8 (5)
N1—C11—C16	111.51 (10)	O5—C25—C23	115.36 (10)
C12—C11—H11	108.8	O6—C25—O5	124.65 (12)
C16—C11—H11	108.8	O6—C25—C23	119.97 (11)
O1—C1—C2—C3	−179.65 (10)	C10—N1—C11—C12	173.99 (10)
O1—C1—C2—C7	−0.41 (16)	C10—N1—C11—C16	−64.33 (13)
O1—C1—C6—C5	−179.53 (10)	C11—N1—C10—C9	171.94 (10)
O1—C9—C10—N1	66.09 (13)	C11—C12—C13—C14	−55.44 (15)
N1—C11—C12—C13	178.03 (11)	C12—C11—C16—C15	−56.86 (13)
N1—C11—C12—O2A	−64.52 (15)	C12—C11—C16—O2B	−173.96 (15)
N1—C11—C16—C15	−177.71 (10)	C12—C13—C14—C15	55.43 (15)
N1—C11—C16—O2B	65.19 (17)	C13—C14—C15—C16	−56.71 (15)
N2—C19—C20—C21	0.06 (18)	C14—C15—C16—C11	58.14 (15)
N2—C19—C24—O3	−3.38 (17)	C14—C15—C16—O2B	−177.61 (16)
N2—C19—C24—O4B	168.5 (9)	C16—C11—C12—C13	55.54 (14)
N2—C19—C24—O4A	−174.4 (12)	C16—C11—C12—O2A	172.98 (13)
N2—C23—C25—O5	8.72 (16)	O2A—C12—C13—C14	178.66 (12)
N2—C23—C25—O6	−170.26 (11)	C19—N2—C23—C22	−1.11 (17)
C1—O1—C9—C10	−176.74 (9)	C19—N2—C23—C25	175.98 (10)
C1—C2—C3—C4	−0.80 (18)	C19—C20—C21—C22	−1.23 (17)
C1—C2—C3—C8	178.90 (12)	C20—C19—C24—O3	178.60 (11)
C2—C1—C6—C5	−0.08 (18)	C20—C19—C24—O4B	−9.5 (9)
C2—C3—C4—C5	−0.02 (19)	C20—C19—C24—O4A	7.6 (12)
C3—C4—C5—C6	0.82 (19)	C20—C21—C22—C23	1.21 (17)
C4—C5—C6—C1	−0.76 (18)	C21—C22—C23—N2	−0.03 (18)
C6—C1—C2—C3	0.85 (18)	C21—C22—C23—C25	−177.08 (11)
C6—C1—C2—C7	−179.91 (11)	C22—C23—C25—O5	−174.05 (10)
C7—C2—C3—C4	179.97 (12)	C22—C23—C25—O6	6.97 (18)
C7—C2—C3—C8	−0.33 (19)	C23—N2—C19—C20	1.09 (17)
C8—C3—C4—C5	−179.72 (13)	C23—N2—C19—C24	−176.84 (10)
C9—O1—C1—C2	174.62 (10)	C24—C19—C20—C21	177.98 (11)
C9—O1—C1—C6	−5.89 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2B—H2B···O4B^i	0.83 (2)	1.89 (3)	2.615 (6)	146 (4)
N1—H1A···O5	0.962 (18)	2.011 (19)	2.8592 (14)	145.9 (15)
N1—H1A···N2	0.962 (18)	2.333 (17)	3.1012 (14)	136.4 (14)
N1—H1B···O3	0.93 (2)	2.17 (2)	2.9693 (14)	143.4 (16)
N1—H1B···O6^ii	0.93 (2)	2.192 (19)	2.8609 (14)	128.1 (15)
O5—H5A···O3^i	0.96 (2)	1.51 (2)	2.4703 (12)	172 (2)
O2A—H2A···O3	0.71 (4)	2.05 (4)	2.739 (2)	164 (4)

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

N-[(2,3-Dimethylphenoxy)propyl]-3-hydroxypiperidinium pyridine-2-carboxylate (3)

Crystal data

C16H26NO2^+·C6H4NO2^−	F(000) = 832
Mr = 386.48	Dx = 1.220 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 8.3611 (1) Å	Cell parameters from 41024 reflections
b = 9.6139 (1) Å	θ = 3.4–77.3°
c = 26.1826 (3) Å	µ = 0.68 mm^−1
β = 91.436 (1)°	T = 100 K
V = 2103.97 (4) Å^3	Needle, clear colourless
Z = 4	0.78 × 0.18 × 0.06 mm

Data collection

Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector	4439 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	4239 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.052
Detector resolution: 10.0000 pixels mm^-1	θmax = 79.1°, θmin = 3.4°
ω scans	h = −10→10
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2019)	k = −11→12
Tmin = 0.406, Tmax = 1.000	l = −33→33
67449 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.041	w = 1/[σ^2(Fo^2) + (0.0463P)^2 + 0.8233P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.108	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.30 e Å^−3
4439 reflections	Δρmin = −0.22 e Å^−3
277 parameters	Extinction correction: SHELXL2019 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0018 (2)
Primary atom site location: dual

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.28264 (12)	0.47807 (9)	0.08853 (3)	0.0331 (2)
O3	0.57691 (10)	0.80523 (9)	0.22368 (3)	0.0290 (2)
O4	0.82898 (10)	0.87916 (9)	0.22497 (4)	0.0318 (2)
N1	0.26895 (11)	0.80116 (10)	0.20065 (4)	0.0216 (2)
N2	0.52713 (13)	0.91285 (12)	0.12837 (4)	0.0322 (2)
C1	0.22953 (15)	0.38192 (13)	0.05326 (5)	0.0278 (3)
C2	0.23012 (16)	0.42727 (13)	0.00238 (5)	0.0305 (3)
C3	0.17820 (16)	0.33556 (15)	−0.03603 (5)	0.0332 (3)
C4	0.12828 (17)	0.20179 (15)	−0.02312 (5)	0.0363 (3)
H4	0.094575	0.140601	−0.048709	0.044*
C5	0.12846 (17)	0.15957 (14)	0.02720 (5)	0.0362 (3)
H5	0.094684	0.070192	0.035199	0.043*
C6	0.17862 (16)	0.24916 (13)	0.06617 (5)	0.0308 (3)
H6	0.178072	0.220788	0.100125	0.037*
C7	0.2839 (2)	0.57353 (15)	−0.00936 (6)	0.0430 (4)
H7A	0.192790	0.634326	−0.010530	0.065*
H7B	0.334884	0.574840	−0.041799	0.065*
H7C	0.358192	0.604407	0.016798	0.065*
C8	0.1762 (2)	0.37951 (18)	−0.09141 (5)	0.0453 (4)
H8A	0.282250	0.405300	−0.100935	0.068*
H8B	0.105663	0.457539	−0.096093	0.068*
H8C	0.139256	0.303613	−0.112422	0.068*
C9	0.28763 (17)	0.43769 (13)	0.14103 (5)	0.0306 (3)
H9A	0.359812	0.359685	0.146191	0.037*
H9B	0.181954	0.410380	0.151751	0.037*
C10	0.34612 (16)	0.56228 (13)	0.17137 (5)	0.0295 (3)
H10A	0.452255	0.587795	0.160531	0.035*
H10B	0.353272	0.538260	0.207338	0.035*
C11	0.23364 (14)	0.68536 (12)	0.16390 (4)	0.0256 (3)
H11A	0.242379	0.720049	0.129296	0.031*
H11B	0.124393	0.654300	0.168148	0.031*
C12	0.18594 (14)	0.93128 (12)	0.18350 (4)	0.0234 (2)
H12A	0.071276	0.915752	0.182190	0.028*
H12B	0.219205	0.955142	0.149373	0.028*
C14	0.17621 (15)	1.01487 (13)	0.27368 (5)	0.0276 (3)
H14A	0.061053	1.003432	0.274606	0.033*
H14B	0.206425	1.089915	0.296726	0.033*
C15	0.25828 (16)	0.88081 (13)	0.29090 (5)	0.0292 (3)
H15A	0.372999	0.895565	0.293249	0.035*
H15B	0.222107	0.855556	0.324571	0.035*
C16	0.22176 (15)	0.76304 (12)	0.25381 (4)	0.0267 (3)
H16A	0.279465	0.680263	0.264727	0.032*
H16B	0.108240	0.742264	0.253925	0.032*
C17	0.66139 (14)	0.94656 (12)	0.15471 (5)	0.0257 (3)
C18	0.76811 (15)	1.04715 (13)	0.13822 (5)	0.0298 (3)
H18	0.861286	1.066378	0.157050	0.036*
C21	0.49793 (18)	0.98122 (17)	0.08457 (5)	0.0402 (3)
H21	0.406477	0.957695	0.065544	0.048*
C19	0.73308 (17)	1.11817 (14)	0.09324 (5)	0.0358 (3)
H19	0.801289	1.187190	0.081732	0.043*
C20	0.59548 (18)	1.08477 (16)	0.06585 (5)	0.0404 (3)
H20	0.568821	1.130669	0.035554	0.048*
C22	0.69180 (13)	0.87066 (11)	0.20505 (5)	0.0234 (2)
O2A	0.14552 (13)	1.16776 (11)	0.20067 (4)	0.0259 (3)	0.796 (3)
C13A	0.22461 (15)	1.05111 (12)	0.21968 (5)	0.0258 (3)	0.796 (3)
H13A	0.340116	1.068460	0.219707	0.031*	0.796 (3)
O2B	0.3667 (5)	1.1012 (5)	0.21084 (17)	0.0306 (13)	0.204 (3)
C13B	0.22461 (15)	1.05111 (12)	0.21968 (5)	0.0258 (3)	0.204 (3)
H13B	0.150656	1.125299	0.209011	0.031*	0.204 (3)
H2B	0.389 (6)	1.172 (4)	0.2289 (19)	0.039*	0.204 (3)
H1	0.380 (2)	0.8149 (18)	0.2016 (6)	0.042 (4)*
H2A	0.161 (3)	1.238 (3)	0.2232 (10)	0.059 (7)*	0.796 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0545 (6)	0.0196 (4)	0.0251 (4)	−0.0060 (4)	0.0001 (4)	−0.0014 (3)
O3	0.0234 (4)	0.0280 (4)	0.0353 (5)	−0.0021 (3)	−0.0018 (3)	0.0071 (4)
O4	0.0248 (4)	0.0285 (5)	0.0418 (5)	−0.0032 (3)	−0.0044 (4)	0.0038 (4)
N1	0.0225 (5)	0.0181 (5)	0.0241 (5)	−0.0013 (4)	−0.0008 (4)	−0.0009 (4)
N2	0.0312 (5)	0.0365 (6)	0.0289 (5)	−0.0012 (5)	0.0006 (4)	0.0024 (5)
C1	0.0359 (6)	0.0201 (6)	0.0275 (6)	0.0013 (5)	0.0012 (5)	−0.0029 (5)
C2	0.0384 (7)	0.0241 (6)	0.0289 (6)	0.0029 (5)	0.0012 (5)	0.0008 (5)
C3	0.0368 (7)	0.0340 (7)	0.0286 (6)	0.0053 (5)	−0.0006 (5)	−0.0028 (5)
C4	0.0412 (7)	0.0322 (7)	0.0353 (7)	−0.0001 (6)	−0.0025 (5)	−0.0110 (5)
C5	0.0447 (8)	0.0236 (6)	0.0402 (7)	−0.0046 (5)	0.0018 (6)	−0.0047 (5)
C6	0.0413 (7)	0.0222 (6)	0.0291 (6)	−0.0024 (5)	0.0023 (5)	−0.0004 (5)
C7	0.0659 (10)	0.0283 (7)	0.0349 (7)	−0.0023 (7)	0.0023 (7)	0.0075 (6)
C8	0.0568 (9)	0.0502 (9)	0.0285 (7)	0.0038 (7)	−0.0042 (6)	−0.0013 (6)
C9	0.0452 (7)	0.0205 (6)	0.0261 (6)	0.0007 (5)	−0.0009 (5)	0.0001 (5)
C10	0.0368 (7)	0.0220 (6)	0.0296 (6)	0.0034 (5)	−0.0039 (5)	−0.0031 (5)
C11	0.0291 (6)	0.0210 (6)	0.0264 (6)	−0.0009 (4)	−0.0037 (4)	−0.0033 (4)
C12	0.0242 (5)	0.0200 (6)	0.0260 (5)	0.0014 (4)	−0.0006 (4)	0.0011 (4)
C14	0.0345 (6)	0.0210 (6)	0.0274 (6)	−0.0032 (5)	0.0046 (5)	−0.0035 (4)
C15	0.0377 (7)	0.0257 (6)	0.0240 (6)	−0.0033 (5)	0.0000 (5)	−0.0015 (5)
C16	0.0335 (6)	0.0210 (6)	0.0257 (6)	−0.0030 (5)	0.0030 (5)	0.0013 (4)
C17	0.0261 (6)	0.0211 (6)	0.0300 (6)	0.0030 (4)	0.0033 (4)	−0.0020 (5)
C18	0.0296 (6)	0.0219 (6)	0.0380 (7)	0.0020 (5)	0.0060 (5)	−0.0005 (5)
C21	0.0393 (7)	0.0517 (9)	0.0297 (6)	−0.0018 (6)	−0.0014 (5)	0.0061 (6)
C19	0.0395 (7)	0.0281 (7)	0.0405 (7)	0.0014 (5)	0.0116 (6)	0.0059 (5)
C20	0.0468 (8)	0.0425 (8)	0.0320 (7)	0.0059 (6)	0.0067 (6)	0.0105 (6)
C22	0.0227 (5)	0.0150 (5)	0.0324 (6)	0.0011 (4)	−0.0003 (4)	−0.0022 (4)
O2A	0.0317 (6)	0.0188 (6)	0.0272 (6)	0.0029 (4)	−0.0017 (4)	0.0016 (4)
C13A	0.0288 (6)	0.0189 (5)	0.0298 (6)	−0.0024 (4)	0.0039 (5)	0.0001 (5)
O2B	0.030 (2)	0.025 (2)	0.037 (2)	−0.0061 (17)	0.0044 (17)	−0.0063 (18)
C13B	0.0288 (6)	0.0189 (5)	0.0298 (6)	−0.0024 (4)	0.0039 (5)	0.0001 (5)

Geometric parameters (Å, º)

O1—C1	1.3725 (14)	C10—C11	1.5211 (16)
O1—C9	1.4278 (15)	C11—H11A	0.9700
O3—C22	1.2569 (14)	C11—H11B	0.9700
O4—C22	1.2507 (14)	C12—H12A	0.9700
N1—C11	1.4960 (14)	C12—H12B	0.9700
N1—C12	1.4942 (14)	C12—C13A	1.5211 (16)
N1—C16	1.5017 (14)	C12—C13B	1.5211 (16)
N1—H1	0.941 (18)	C14—H14A	0.9700
N2—C17	1.3424 (16)	C14—H14B	0.9700
N2—C21	1.3390 (18)	C14—C15	1.5232 (17)
C1—C2	1.4018 (17)	C14—C13A	1.5208 (16)
C1—C6	1.3898 (18)	C14—C13B	1.5208 (16)
C2—C3	1.3984 (18)	C15—H15A	0.9700
C2—C7	1.5103 (18)	C15—H15B	0.9700
C3—C4	1.396 (2)	C15—C16	1.5177 (16)
C3—C8	1.5100 (19)	C16—H16A	0.9700
C4—H4	0.9300	C16—H16B	0.9700
C4—C5	1.379 (2)	C17—C18	1.3917 (17)
C5—H5	0.9300	C17—C22	1.5224 (17)
C5—C6	1.3920 (18)	C18—H18	0.9300
C6—H6	0.9300	C18—C19	1.3863 (19)
C7—H7A	0.9600	C21—H21	0.9300
C7—H7B	0.9600	C21—C20	1.384 (2)
C7—H7C	0.9600	C19—H19	0.9300
C8—H8A	0.9600	C19—C20	1.378 (2)
C8—H8B	0.9600	C20—H20	0.9300
C8—H8C	0.9600	O2A—C13A	1.3878 (16)
C9—H9A	0.9700	O2A—H2A	0.90 (3)
C9—H9B	0.9700	C13A—H13A	0.9800
C9—C10	1.5118 (17)	O2B—C13B	1.308 (4)
C10—H10A	0.9700	O2B—H2B	0.844 (19)
C10—H10B	0.9700	C13B—H13B	0.9800
C1—O1—C9	117.76 (9)	N1—C12—H12B	109.5
C11—N1—C16	111.24 (9)	N1—C12—C13A	110.92 (9)
C11—N1—H1	107.5 (10)	N1—C12—C13B	110.92 (9)
C12—N1—C11	110.30 (9)	H12A—C12—H12B	108.0
C12—N1—C16	110.61 (9)	C13A—C12—H12A	109.5
C12—N1—H1	110.0 (11)	C13A—C12—H12B	109.5
C16—N1—H1	107.0 (10)	H14A—C14—H14B	108.2
C21—N2—C17	116.98 (12)	C15—C14—H14A	109.7
O1—C1—C2	114.91 (11)	C15—C14—H14B	109.7
O1—C1—C6	123.42 (11)	C13A—C14—H14A	109.7
C6—C1—C2	121.67 (11)	C13A—C14—H14B	109.7
C1—C2—C7	119.41 (12)	C13A—C14—C15	109.92 (10)
C3—C2—C1	118.62 (12)	C13B—C14—C15	109.92 (10)
C3—C2—C7	121.96 (12)	C14—C15—H15A	109.4
C2—C3—C8	120.67 (13)	C14—C15—H15B	109.4
C4—C3—C2	119.73 (12)	H15A—C15—H15B	108.0
C4—C3—C8	119.60 (13)	C16—C15—C14	111.09 (10)
C3—C4—H4	119.7	C16—C15—H15A	109.4
C5—C4—C3	120.63 (12)	C16—C15—H15B	109.4
C5—C4—H4	119.7	N1—C16—C15	110.96 (9)
C4—C5—H5	119.6	N1—C16—H16A	109.4
C4—C5—C6	120.76 (13)	N1—C16—H16B	109.4
C6—C5—H5	119.6	C15—C16—H16A	109.4
C1—C6—C5	118.59 (12)	C15—C16—H16B	109.4
C1—C6—H6	120.7	H16A—C16—H16B	108.0
C5—C6—H6	120.7	N2—C17—C18	122.87 (12)
C2—C7—H7A	109.5	N2—C17—C22	116.64 (10)
C2—C7—H7B	109.5	C18—C17—C22	120.48 (11)
C2—C7—H7C	109.5	C17—C18—H18	120.6
H7A—C7—H7B	109.5	C19—C18—C17	118.84 (12)
H7A—C7—H7C	109.5	C19—C18—H18	120.6
H7B—C7—H7C	109.5	N2—C21—H21	118.0
C3—C8—H8A	109.5	N2—C21—C20	124.04 (14)
C3—C8—H8B	109.5	C20—C21—H21	118.0
C3—C8—H8C	109.5	C18—C19—H19	120.6
H8A—C8—H8B	109.5	C20—C19—C18	118.89 (13)
H8A—C8—H8C	109.5	C20—C19—H19	120.6
H8B—C8—H8C	109.5	C21—C20—H20	120.8
O1—C9—H9A	110.3	C19—C20—C21	118.36 (13)
O1—C9—H9B	110.3	C19—C20—H20	120.8
O1—C9—C10	106.96 (10)	O3—C22—C17	117.59 (10)
H9A—C9—H9B	108.6	O4—C22—O3	124.94 (11)
C10—C9—H9A	110.3	O4—C22—C17	117.47 (10)
C10—C9—H9B	110.3	C13A—O2A—H2A	108.1 (16)
C9—C10—H10A	109.4	C12—C13A—H13A	108.9
C9—C10—H10B	109.4	C14—C13A—C12	110.37 (10)
C9—C10—C11	110.98 (10)	C14—C13A—H13A	108.9
H10A—C10—H10B	108.0	O2A—C13A—C12	107.26 (10)
C11—C10—H10A	109.4	O2A—C13A—C14	112.52 (10)
C11—C10—H10B	109.4	O2A—C13A—H13A	108.9
N1—C11—C10	112.63 (9)	C13B—O2B—H2B	113 (3)
N1—C11—H11A	109.1	C12—C13B—H13B	104.5
N1—C11—H11B	109.1	C14—C13B—C12	110.37 (10)
C10—C11—H11A	109.1	C14—C13B—H13B	104.5
C10—C11—H11B	109.1	O2B—C13B—C12	110.4 (2)
H11A—C11—H11B	107.8	O2B—C13B—C14	120.9 (2)
N1—C12—H12A	109.5	O2B—C13B—H13B	104.5
O1—C1—C2—C3	179.83 (11)	C9—O1—C1—C6	0.99 (18)
O1—C1—C2—C7	−1.14 (18)	C9—C10—C11—N1	168.95 (10)
O1—C1—C6—C5	−179.43 (12)	C11—N1—C12—C13A	−178.35 (9)
O1—C9—C10—C11	60.28 (14)	C11—N1—C12—C13B	−178.35 (9)
N1—C12—C13A—C14	−58.08 (13)	C11—N1—C16—C15	179.86 (10)
N1—C12—C13A—O2A	179.02 (9)	C12—N1—C11—C10	165.34 (10)
N1—C12—C13B—C14	−58.08 (13)	C12—N1—C16—C15	−57.19 (13)
N1—C12—C13B—O2B	78.1 (2)	C14—C15—C16—N1	56.35 (13)
N2—C17—C18—C19	1.49 (19)	C15—C14—C13A—C12	56.39 (13)
N2—C17—C22—O3	−14.60 (16)	C15—C14—C13A—O2A	176.16 (10)
N2—C17—C22—O4	166.00 (11)	C15—C14—C13B—C12	56.39 (13)
N2—C21—C20—C19	1.4 (2)	C15—C14—C13B—O2B	−74.5 (3)
C1—O1—C9—C10	−178.72 (11)	C16—N1—C11—C10	−71.54 (12)
C1—C2—C3—C4	−0.39 (19)	C16—N1—C12—C13A	58.15 (12)
C1—C2—C3—C8	179.85 (13)	C16—N1—C12—C13B	58.15 (12)
C2—C1—C6—C5	0.5 (2)	C17—N2—C21—C20	−1.3 (2)
C2—C3—C4—C5	0.5 (2)	C17—C18—C19—C20	−1.31 (19)
C3—C4—C5—C6	−0.1 (2)	C18—C17—C22—O3	164.31 (11)
C4—C5—C6—C1	−0.4 (2)	C18—C17—C22—O4	−15.09 (17)
C6—C1—C2—C3	−0.1 (2)	C18—C19—C20—C21	0.0 (2)
C6—C1—C2—C7	178.90 (13)	C21—N2—C17—C18	−0.21 (19)
C7—C2—C3—C4	−179.40 (13)	C21—N2—C17—C22	178.67 (12)
C7—C2—C3—C8	0.8 (2)	C22—C17—C18—C19	−177.35 (11)
C8—C3—C4—C5	−179.72 (13)	C13A—C14—C15—C16	−55.84 (13)
C9—O1—C1—C2	−178.97 (11)	C13B—C14—C15—C16	−55.84 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.941 (18)	1.731 (17)	2.6300 (13)	158.9 (15)
N1—H1···N2	0.941 (18)	2.488 (17)	3.0982 (14)	122.7 (12)