Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615004295/sk3581sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615004295/sk3581Isup2.hkl | |
Chemdraw file https://doi.org/10.1107/S2053229615004295/sk3581Isup3.cdx | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615004295/sk3581Isup4.cml |
CCDC reference: 1051738
Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEPII (Johnson, 1976), Mercury (Macrae et al., 2008) and CrystalStructure (Rigaku, 2007); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2015).
C12H16NO3+·Cl− | Dx = 1.366 Mg m−3 |
Mr = 257.71 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, P212121 | Cell parameters from 3179 reflections |
a = 6.90225 (16) Å | θ = 6.4–73.0° |
b = 7.13000 (16) Å | µ = 2.69 mm−1 |
c = 25.4692 (5) Å | T = 160 K |
V = 1253.42 (5) Å3 | Needle, pale yellow |
Z = 4 | 0.30 × 0.06 × 0.03 mm |
F(000) = 544 |
Oxford Diffraction SuperNova (dual radiation) diffractometer | 2421 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 2286 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.032 |
Detector resolution: 10.3801 pixels mm-1 | θmax = 74.8°, θmin = 3.5° |
ω scans | h = −8→8 |
Absorption correction: gaussian (CrysAlisPro; Agilent, 2014) | k = −8→8 |
Tmin = 0.707, Tmax = 0.923 | l = −31→31 |
7202 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.067 | w = 1/[σ2(Fo2) + (0.1079P)2 + 1.0836P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.180 | (Δ/σ)max = 0.001 |
S = 1.11 | Δρmax = 0.74 e Å−3 |
2421 reflections | Δρmin = −0.34 e Å−3 |
157 parameters | Absolute structure: Refined as an inversion twin using 929 Friedel pairs |
0 restraints | Absolute structure parameter: 0.50 (5) |
Experimental. Solvent used: 50:50 v.v. MeOH-H2O Cooling Device: Oxford Instruments Cryojet XL Crystal mount: on a glass fibre Frames collected: 2184 Seconds exposure per frame: 5.0–75.0 Degrees rotation per frame: 0.5 Crystal-detector distance (mm): 55.0 Client: Stan Cameron Sample code: ethlone hydrochloride (L1407) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refined as a 2-component inversion twin using 929 Friedel pairs |
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.0103 (2) | 0.35002 (17) | 0.80071 (4) | 0.0414 (4) | |
O1 | 0.1371 (7) | 0.1702 (6) | 0.58409 (15) | 0.0469 (10) | |
O2 | 0.0680 (8) | 0.4897 (6) | 0.40324 (15) | 0.0494 (11) | |
O3 | 0.0217 (6) | 0.8065 (5) | 0.41849 (13) | 0.0424 (9) | |
N1 | 0.1330 (7) | 0.2704 (6) | 0.68548 (16) | 0.0335 (9) | |
H1 | 0.0832 | 0.2945 | 0.7179 | 0.040* | |
H2 | 0.1048 | 0.1491 | 0.6774 | 0.040* | |
C1 | 0.0643 (8) | 0.4676 (8) | 0.54772 (19) | 0.0337 (11) | |
C2 | 0.0773 (9) | 0.3968 (8) | 0.4959 (2) | 0.0393 (12) | |
H21 | 0.0992 | 0.2676 | 0.4889 | 0.047* | |
C3 | 0.0565 (8) | 0.5253 (8) | 0.45632 (19) | 0.0360 (12) | |
C4 | 0.0302 (7) | 0.7116 (7) | 0.46539 (19) | 0.0333 (11) | |
C5 | 0.0214 (7) | 0.7849 (7) | 0.51485 (18) | 0.0319 (10) | |
H5 | 0.0059 | 0.9156 | 0.5206 | 0.038* | |
C6 | 0.0361 (7) | 0.6590 (7) | 0.55644 (18) | 0.0323 (10) | |
H6 | 0.0268 | 0.7042 | 0.5914 | 0.039* | |
C7 | 0.0879 (8) | 0.3315 (8) | 0.59123 (19) | 0.0343 (10) | |
C8 | 0.0363 (8) | 0.3947 (7) | 0.64665 (17) | 0.0311 (11) | |
H8 | 0.0811 | 0.5267 | 0.6520 | 0.037* | |
C9 | −0.1808 (9) | 0.3853 (9) | 0.6540 (2) | 0.0436 (14) | |
H91 | −0.2247 | 0.2557 | 0.6493 | 0.065* | |
H92 | −0.2442 | 0.4660 | 0.6280 | 0.065* | |
H93 | −0.2141 | 0.4281 | 0.6894 | 0.065* | |
C10 | 0.3466 (8) | 0.2923 (8) | 0.6877 (2) | 0.0389 (12) | |
H101 | 0.3792 | 0.4244 | 0.6957 | 0.047* | |
H102 | 0.4031 | 0.2608 | 0.6530 | 0.047* | |
C11 | 0.4327 (9) | 0.1655 (9) | 0.7293 (2) | 0.0441 (13) | |
H111 | 0.3945 | 0.0355 | 0.7224 | 0.066* | |
H112 | 0.3850 | 0.2036 | 0.7640 | 0.066* | |
H113 | 0.5742 | 0.1755 | 0.7285 | 0.066* | |
C12 | 0.0225 (9) | 0.6636 (8) | 0.37870 (19) | 0.0437 (12) | |
H121 | −0.1062 | 0.6562 | 0.3617 | 0.052* | |
H122 | 0.1203 | 0.6934 | 0.3515 | 0.052* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0673 (8) | 0.0288 (6) | 0.0282 (5) | 0.0097 (6) | 0.0067 (6) | 0.0024 (4) |
O1 | 0.075 (3) | 0.033 (2) | 0.0327 (18) | 0.004 (2) | 0.0023 (18) | −0.0044 (16) |
O2 | 0.080 (3) | 0.043 (2) | 0.0249 (17) | −0.005 (2) | 0.0033 (18) | −0.0025 (16) |
O3 | 0.059 (2) | 0.042 (2) | 0.0267 (16) | −0.006 (2) | 0.0019 (16) | 0.0035 (14) |
N1 | 0.046 (2) | 0.027 (2) | 0.0273 (18) | 0.0010 (18) | 0.0011 (17) | −0.0015 (16) |
C1 | 0.037 (2) | 0.036 (3) | 0.028 (2) | −0.005 (2) | 0.0015 (19) | −0.001 (2) |
C2 | 0.051 (3) | 0.037 (3) | 0.030 (2) | −0.006 (2) | 0.003 (2) | −0.003 (2) |
C3 | 0.040 (3) | 0.042 (3) | 0.026 (2) | −0.006 (2) | 0.0033 (19) | −0.002 (2) |
C4 | 0.033 (2) | 0.037 (3) | 0.030 (2) | −0.008 (2) | 0.0016 (18) | 0.0057 (19) |
C5 | 0.033 (2) | 0.029 (2) | 0.034 (2) | −0.002 (2) | 0.003 (2) | 0.0005 (18) |
C6 | 0.035 (2) | 0.034 (2) | 0.028 (2) | −0.004 (2) | 0.0006 (17) | −0.0041 (19) |
C7 | 0.043 (2) | 0.032 (3) | 0.028 (2) | −0.005 (2) | −0.0032 (19) | −0.001 (2) |
C8 | 0.046 (3) | 0.021 (2) | 0.026 (2) | −0.003 (2) | −0.0004 (19) | −0.0007 (16) |
C9 | 0.048 (3) | 0.050 (4) | 0.033 (3) | 0.000 (3) | 0.004 (2) | −0.001 (2) |
C10 | 0.043 (3) | 0.040 (3) | 0.033 (2) | −0.005 (2) | 0.001 (2) | 0.002 (2) |
C11 | 0.050 (3) | 0.044 (3) | 0.038 (3) | −0.005 (3) | −0.004 (2) | 0.009 (2) |
C12 | 0.059 (3) | 0.044 (3) | 0.027 (2) | −0.005 (3) | 0.000 (2) | 0.000 (2) |
O1—C7 | 1.213 (7) | C5—H5 | 0.9500 |
O2—C3 | 1.378 (6) | C6—H6 | 0.9500 |
O2—C12 | 1.424 (7) | C7—C8 | 1.524 (7) |
O3—C4 | 1.374 (6) | C8—C9 | 1.511 (8) |
O3—C12 | 1.437 (6) | C8—H8 | 1.0000 |
N1—C10 | 1.484 (7) | C9—H91 | 0.9800 |
N1—C8 | 1.486 (6) | C9—H92 | 0.9800 |
N1—H1 | 0.9100 | C9—H93 | 0.9800 |
N1—H2 | 0.9100 | C10—C11 | 1.515 (8) |
C1—C6 | 1.396 (7) | C10—H101 | 0.9900 |
C1—C2 | 1.417 (7) | C10—H102 | 0.9900 |
C1—C7 | 1.482 (7) | C11—H111 | 0.9800 |
C2—C3 | 1.369 (8) | C11—H112 | 0.9800 |
C2—H21 | 0.9500 | C11—H113 | 0.9800 |
C3—C4 | 1.360 (8) | C12—H121 | 0.9900 |
C4—C5 | 1.365 (7) | C12—H122 | 0.9900 |
C5—C6 | 1.392 (7) | ||
C3—O2—C12 | 104.9 (4) | N1—C8—C7 | 109.6 (4) |
C4—O3—C12 | 105.3 (4) | C9—C8—C7 | 109.5 (4) |
C10—N1—C8 | 114.1 (4) | N1—C8—H8 | 109.4 |
C10—N1—H1 | 108.7 | C9—C8—H8 | 109.4 |
C8—N1—H1 | 108.7 | C7—C8—H8 | 109.4 |
C10—N1—H2 | 108.7 | C8—C9—H91 | 109.5 |
C8—N1—H2 | 108.7 | C8—C9—H92 | 109.5 |
H1—N1—H2 | 107.6 | H91—C9—H92 | 109.5 |
C6—C1—C2 | 120.4 (5) | C8—C9—H93 | 109.5 |
C6—C1—C7 | 122.5 (4) | H91—C9—H93 | 109.5 |
C2—C1—C7 | 117.2 (5) | H92—C9—H93 | 109.5 |
C3—C2—C1 | 116.1 (5) | N1—C10—C11 | 110.7 (4) |
C3—C2—H21 | 121.9 | N1—C10—H101 | 109.5 |
C1—C2—H21 | 121.9 | C11—C10—H101 | 109.5 |
C4—C3—C2 | 122.9 (5) | N1—C10—H102 | 109.5 |
C4—C3—O2 | 110.7 (5) | C11—C10—H102 | 109.5 |
C2—C3—O2 | 126.3 (5) | H101—C10—H102 | 108.1 |
C3—C4—C5 | 122.4 (5) | C10—C11—H111 | 109.5 |
C3—C4—O3 | 109.8 (4) | C10—C11—H112 | 109.5 |
C5—C4—O3 | 127.7 (5) | H111—C11—H112 | 109.5 |
C4—C5—C6 | 116.9 (5) | C10—C11—H113 | 109.5 |
C4—C5—H5 | 121.6 | H111—C11—H113 | 109.5 |
C6—C5—H5 | 121.6 | H112—C11—H113 | 109.5 |
C5—C6—C1 | 121.3 (4) | O2—C12—O3 | 108.0 (4) |
C5—C6—H6 | 119.4 | O2—C12—H121 | 110.1 |
C1—C6—H6 | 119.4 | O3—C12—H121 | 110.1 |
O1—C7—C1 | 122.7 (5) | O2—C12—H122 | 110.1 |
O1—C7—C8 | 119.0 (5) | O3—C12—H122 | 110.1 |
C1—C7—C8 | 118.2 (5) | H121—C12—H122 | 108.4 |
N1—C8—C9 | 109.7 (4) | ||
C6—C1—C2—C3 | −1.3 (8) | C2—C1—C6—C5 | −0.4 (8) |
C7—C1—C2—C3 | −179.5 (5) | C7—C1—C6—C5 | 177.6 (5) |
C1—C2—C3—C4 | 1.8 (8) | C6—C1—C7—O1 | −170.2 (5) |
C1—C2—C3—O2 | 178.5 (5) | C2—C1—C7—O1 | 7.9 (8) |
C12—O2—C3—C4 | −7.2 (6) | C6—C1—C7—C8 | 13.5 (7) |
C12—O2—C3—C2 | 175.8 (6) | C2—C1—C7—C8 | −168.3 (5) |
C2—C3—C4—C5 | −0.4 (9) | C10—N1—C8—C9 | −170.5 (4) |
O2—C3—C4—C5 | −177.5 (5) | C10—N1—C8—C7 | 69.3 (5) |
C2—C3—C4—O3 | 177.6 (5) | O1—C7—C8—N1 | 23.9 (7) |
O2—C3—C4—O3 | 0.5 (7) | C1—C7—C8—N1 | −159.8 (4) |
C12—O3—C4—C3 | 6.4 (6) | O1—C7—C8—C9 | −96.4 (6) |
C12—O3—C4—C5 | −175.8 (5) | C1—C7—C8—C9 | 79.9 (6) |
C3—C4—C5—C6 | −1.4 (8) | C8—N1—C10—C11 | 178.2 (4) |
O3—C4—C5—C6 | −179.1 (5) | C3—O2—C12—O3 | 10.9 (6) |
C4—C5—C6—C1 | 1.8 (7) | C4—O3—C12—O2 | −10.7 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl1 | 0.91 | 2.24 | 3.149 (4) | 174 |
N1—H2···Cl1i | 0.91 | 2.30 | 3.134 (5) | 153 |
Symmetry code: (i) −x, y−1/2, −z+3/2. |
Computation | ΔG (kJ mol-1) |
A, gas phase | 0 |
AB, gas phase | 34 |
B, gas phase | 35 |
A, MeOH | 0 |
AB, MeOH | 31 |
B, MeOH | 14 |
A, HOH | 0 |
AB, HOH | 30 |
B, HOH | 12 |
(a) Computations done at 288 K and 318 K yielded essentially the same relative energies. |