Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621013401/dg3025sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229621013401/dg3025ch20_pk1269sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229621013401/dg3025ch20_pk1270sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229621013401/dg3025ch20_pk1271sup4.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621013401/dg3025ch20_pk1269sup5.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621013401/dg3025ch20_pk1270sup6.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621013401/dg3025ch20_pk1271sup7.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229621013401/dg3025sup8.pdf |
CCDC references: 2041927; 2041926; 2041925
For all structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015).
C17H26NO+·Cl− | F(000) = 640 |
Mr = 295.84 | Dx = 1.151 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 17.0494 (9) Å | Cell parameters from 2886 reflections |
b = 6.9334 (3) Å | θ = 5.4–73.6° |
c = 15.241 (1) Å | µ = 1.94 mm−1 |
β = 108.635 (7)° | T = 294 K |
V = 1707.19 (17) Å3 | Polyhedron, colorless |
Z = 4 | 0.08 × 0.08 × 0.04 mm |
Agilent SuperNova diffractometer with an Atlas detector | 3400 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 2207 reflections with I > 2σ(I) |
Detector resolution: 10.4498 pixels mm-1 | Rint = 0.047 |
ω scans | θmax = 74.3°, θmin = 5.5° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −21→16 |
Tmin = 0.480, Tmax = 1.000 | k = −8→8 |
11711 measured reflections | l = −18→18 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.050 | w = 1/[σ2(Fo2) + (0.0618P)2 + 0.260P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.143 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.20 e Å−3 |
3400 reflections | Δρmin = −0.16 e Å−3 |
184 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0019 (3) |
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. The single-crystal X-ray experiments were performed at room temperature. The data were collected using a SuperNova kappa diffractometer with Atlas CCD detector (Agilent Technologies, Santa Clara, CA, USA). For the integration of the collected data, the CrysAlis PRO software (version 1.171.38.41q, 2015; Rigaku Oxford Diffraction, Rigaku, Tokyo, Japan) was used. The structures were solved using direct methods with the SHELXS2013 software and the solutions were refined using SHELXL2018/3 program (Sheldrick, 2015). |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.61628 (4) | 0.21454 (8) | 0.18970 (5) | 0.0621 (2) | |
O1 | 0.78864 (13) | 0.5776 (3) | 0.21150 (16) | 0.0775 (6) | |
C1 | 0.85218 (15) | 0.8538 (4) | 0.29481 (19) | 0.0528 (6) | |
C2 | 0.84184 (17) | 1.0456 (4) | 0.3143 (2) | 0.0702 (8) | |
H2 | 0.788906 | 1.096729 | 0.301281 | 0.084* | |
C3 | 0.91037 (18) | 1.1609 (5) | 0.3530 (3) | 0.0789 (9) | |
H3 | 0.902740 | 1.289614 | 0.365389 | 0.095* | |
C4 | 0.98949 (17) | 1.0901 (5) | 0.3736 (2) | 0.0696 (8) | |
C5 | 0.99912 (18) | 0.9007 (5) | 0.3519 (2) | 0.0785 (9) | |
H5 | 1.052157 | 0.850882 | 0.363885 | 0.094* | |
C6 | 0.93187 (16) | 0.7839 (4) | 0.3128 (2) | 0.0686 (8) | |
H6 | 0.939955 | 0.656695 | 0.298373 | 0.082* | |
C7 | 0.78160 (15) | 0.7207 (4) | 0.25425 (19) | 0.0536 (6) | |
C8 | 0.70078 (14) | 0.7615 (3) | 0.27361 (18) | 0.0484 (6) | |
H8 | 0.688691 | 0.899563 | 0.264428 | 0.058* | |
N1 | 0.63213 (11) | 0.6520 (3) | 0.20618 (14) | 0.0464 (5) | |
H1 | 0.646988 | 0.514934 | 0.212087 | 0.056* | |
C9 | 0.61602 (19) | 0.7095 (4) | 0.10622 (19) | 0.0698 (8) | |
H9A | 0.629238 | 0.604290 | 0.071400 | 0.084* | |
H9B | 0.649002 | 0.820988 | 0.102048 | 0.084* | |
C10 | 0.5243 (2) | 0.7569 (5) | 0.0696 (2) | 0.0929 (12) | |
H10A | 0.515502 | 0.894662 | 0.072396 | 0.111* | |
H10B | 0.500605 | 0.714370 | 0.005961 | 0.111* | |
C11 | 0.48658 (18) | 0.6512 (5) | 0.1310 (2) | 0.0776 (9) | |
H11A | 0.477739 | 0.516410 | 0.113569 | 0.093* | |
H11B | 0.434327 | 0.708661 | 0.129621 | 0.093* | |
C12 | 0.55060 (15) | 0.6738 (4) | 0.2243 (2) | 0.0596 (7) | |
H12A | 0.544286 | 0.575216 | 0.266684 | 0.072* | |
H12B | 0.546496 | 0.799652 | 0.250288 | 0.072* | |
C13 | 0.71033 (15) | 0.7113 (4) | 0.37435 (17) | 0.0523 (6) | |
H13A | 0.750494 | 0.798606 | 0.414410 | 0.063* | |
H13B | 0.657781 | 0.733874 | 0.384584 | 0.063* | |
C14 | 0.73739 (17) | 0.5056 (4) | 0.40294 (18) | 0.0589 (7) | |
H14A | 0.702604 | 0.418251 | 0.357157 | 0.071* | |
H14B | 0.793801 | 0.489106 | 0.402652 | 0.071* | |
C15 | 0.7334 (2) | 0.4492 (5) | 0.4974 (2) | 0.0711 (8) | |
H15A | 0.768370 | 0.535813 | 0.543392 | 0.085* | |
H15B | 0.677029 | 0.465355 | 0.497886 | 0.085* | |
C16 | 0.7600 (3) | 0.2468 (6) | 0.5238 (3) | 0.1066 (13) | |
H16A | 0.725128 | 0.159849 | 0.479130 | 0.160* | |
H16B | 0.755754 | 0.219516 | 0.583829 | 0.160* | |
H16C | 0.816398 | 0.230562 | 0.525367 | 0.160* | |
C17 | 1.0640 (2) | 1.2168 (6) | 0.4200 (3) | 0.0996 (12) | |
H17A | 1.078255 | 1.205163 | 0.485982 | 0.149* | |
H17B | 1.050735 | 1.348696 | 0.402216 | 0.149* | |
H17C | 1.109971 | 1.176513 | 0.400987 | 0.149* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0698 (4) | 0.0326 (3) | 0.0768 (5) | 0.0022 (3) | 0.0135 (3) | −0.0021 (3) |
O1 | 0.0762 (13) | 0.0633 (12) | 0.1053 (17) | −0.0081 (10) | 0.0463 (12) | −0.0286 (12) |
C1 | 0.0487 (13) | 0.0505 (13) | 0.0602 (15) | −0.0016 (11) | 0.0188 (11) | 0.0001 (12) |
C2 | 0.0499 (14) | 0.0529 (16) | 0.108 (3) | −0.0041 (12) | 0.0251 (15) | −0.0080 (16) |
C3 | 0.0607 (17) | 0.0615 (18) | 0.114 (3) | −0.0131 (13) | 0.0276 (17) | −0.0149 (18) |
C4 | 0.0553 (16) | 0.086 (2) | 0.0664 (18) | −0.0167 (14) | 0.0179 (14) | −0.0018 (16) |
C5 | 0.0469 (15) | 0.095 (3) | 0.088 (2) | 0.0052 (15) | 0.0144 (15) | 0.0022 (19) |
C6 | 0.0554 (15) | 0.0667 (17) | 0.084 (2) | 0.0064 (13) | 0.0224 (14) | −0.0010 (16) |
C7 | 0.0599 (14) | 0.0435 (13) | 0.0606 (15) | 0.0006 (11) | 0.0238 (12) | −0.0003 (12) |
C8 | 0.0472 (12) | 0.0342 (11) | 0.0621 (15) | −0.0016 (9) | 0.0151 (11) | −0.0043 (10) |
N1 | 0.0505 (11) | 0.0318 (9) | 0.0539 (12) | 0.0006 (7) | 0.0127 (9) | 0.0018 (8) |
C9 | 0.091 (2) | 0.0595 (16) | 0.0535 (16) | −0.0123 (15) | 0.0160 (15) | 0.0080 (13) |
C10 | 0.108 (3) | 0.066 (2) | 0.072 (2) | 0.0056 (18) | −0.0191 (19) | 0.0051 (16) |
C11 | 0.0610 (17) | 0.0709 (19) | 0.086 (2) | 0.0076 (14) | 0.0019 (16) | −0.0114 (17) |
C12 | 0.0455 (13) | 0.0559 (16) | 0.0729 (18) | 0.0052 (11) | 0.0125 (12) | −0.0050 (13) |
C13 | 0.0516 (13) | 0.0485 (13) | 0.0562 (15) | −0.0006 (11) | 0.0164 (11) | −0.0128 (12) |
C14 | 0.0636 (15) | 0.0561 (15) | 0.0559 (15) | 0.0095 (12) | 0.0176 (13) | 0.0012 (12) |
C15 | 0.0793 (19) | 0.079 (2) | 0.0570 (17) | −0.0020 (15) | 0.0239 (15) | 0.0016 (15) |
C16 | 0.119 (3) | 0.111 (3) | 0.096 (3) | 0.035 (2) | 0.043 (2) | 0.047 (2) |
C17 | 0.0670 (19) | 0.130 (3) | 0.095 (3) | −0.035 (2) | 0.0172 (18) | −0.017 (2) |
O1—C7 | 1.214 (3) | C10—C11 | 1.487 (5) |
C1—C6 | 1.385 (4) | C10—H10A | 0.9700 |
C1—C2 | 1.386 (4) | C10—H10B | 0.9700 |
C1—C7 | 1.485 (3) | C11—C12 | 1.499 (4) |
C2—C3 | 1.383 (4) | C11—H11A | 0.9700 |
C2—H2 | 0.9300 | C11—H11B | 0.9700 |
C3—C4 | 1.374 (4) | C12—H12A | 0.9700 |
C3—H3 | 0.9300 | C12—H12B | 0.9700 |
C4—C5 | 1.376 (4) | C13—C14 | 1.519 (4) |
C4—C17 | 1.520 (4) | C13—H13A | 0.9700 |
C5—C6 | 1.374 (4) | C13—H13B | 0.9700 |
C5—H5 | 0.9300 | C14—C15 | 1.514 (4) |
C6—H6 | 0.9300 | C14—H14A | 0.9700 |
C7—C8 | 1.525 (3) | C14—H14B | 0.9700 |
C8—N1 | 1.495 (3) | C15—C16 | 1.491 (5) |
C8—C13 | 1.531 (4) | C15—H15A | 0.9700 |
C8—H8 | 0.9800 | C15—H15B | 0.9700 |
N1—C12 | 1.509 (3) | C16—H16A | 0.9600 |
N1—C9 | 1.513 (3) | C16—H16B | 0.9600 |
N1—H1 | 0.9800 | C16—H16C | 0.9600 |
C9—C10 | 1.518 (5) | C17—H17A | 0.9600 |
C9—H9A | 0.9700 | C17—H17B | 0.9600 |
C9—H9B | 0.9700 | C17—H17C | 0.9600 |
C6—C1—C2 | 118.5 (2) | H10A—C10—H10B | 108.8 |
C6—C1—C7 | 118.6 (2) | C10—C11—C12 | 102.4 (2) |
C2—C1—C7 | 122.9 (2) | C10—C11—H11A | 111.3 |
C3—C2—C1 | 119.9 (3) | C12—C11—H11A | 111.3 |
C3—C2—H2 | 120.1 | C10—C11—H11B | 111.3 |
C1—C2—H2 | 120.1 | C12—C11—H11B | 111.3 |
C4—C3—C2 | 121.7 (3) | H11A—C11—H11B | 109.2 |
C4—C3—H3 | 119.2 | C11—C12—N1 | 104.5 (2) |
C2—C3—H3 | 119.2 | C11—C12—H12A | 110.9 |
C3—C4—C5 | 118.0 (3) | N1—C12—H12A | 110.9 |
C3—C4—C17 | 120.9 (3) | C11—C12—H12B | 110.9 |
C5—C4—C17 | 121.1 (3) | N1—C12—H12B | 110.9 |
C6—C5—C4 | 121.3 (3) | H12A—C12—H12B | 108.9 |
C6—C5—H5 | 119.4 | C14—C13—C8 | 115.2 (2) |
C4—C5—H5 | 119.4 | C14—C13—H13A | 108.5 |
C5—C6—C1 | 120.6 (3) | C8—C13—H13A | 108.5 |
C5—C6—H6 | 119.7 | C14—C13—H13B | 108.5 |
C1—C6—H6 | 119.7 | C8—C13—H13B | 108.5 |
O1—C7—C1 | 121.7 (2) | H13A—C13—H13B | 107.5 |
O1—C7—C8 | 120.4 (2) | C15—C14—C13 | 114.4 (2) |
C1—C7—C8 | 117.8 (2) | C15—C14—H14A | 108.7 |
N1—C8—C7 | 109.29 (19) | C13—C14—H14A | 108.7 |
N1—C8—C13 | 112.52 (19) | C15—C14—H14B | 108.7 |
C7—C8—C13 | 109.8 (2) | C13—C14—H14B | 108.7 |
N1—C8—H8 | 108.4 | H14A—C14—H14B | 107.6 |
C7—C8—H8 | 108.4 | C16—C15—C14 | 113.4 (3) |
C13—C8—H8 | 108.4 | C16—C15—H15A | 108.9 |
C8—N1—C12 | 112.83 (19) | C14—C15—H15A | 108.9 |
C8—N1—C9 | 114.14 (19) | C16—C15—H15B | 108.9 |
C12—N1—C9 | 106.0 (2) | C14—C15—H15B | 108.9 |
C8—N1—H1 | 107.9 | H15A—C15—H15B | 107.7 |
C12—N1—H1 | 107.9 | C15—C16—H16A | 109.5 |
C9—N1—H1 | 107.9 | C15—C16—H16B | 109.5 |
N1—C9—C10 | 105.2 (3) | H16A—C16—H16B | 109.5 |
N1—C9—H9A | 110.7 | C15—C16—H16C | 109.5 |
C10—C9—H9A | 110.7 | H16A—C16—H16C | 109.5 |
N1—C9—H9B | 110.7 | H16B—C16—H16C | 109.5 |
C10—C9—H9B | 110.7 | C4—C17—H17A | 109.5 |
H9A—C9—H9B | 108.8 | C4—C17—H17B | 109.5 |
C11—C10—C9 | 105.3 (2) | H17A—C17—H17B | 109.5 |
C11—C10—H10A | 110.7 | C4—C17—H17C | 109.5 |
C9—C10—H10A | 110.7 | H17A—C17—H17C | 109.5 |
C11—C10—H10B | 110.7 | H17B—C17—H17C | 109.5 |
C9—C10—H10B | 110.7 |
C16H24NO+·Cl− | F(000) = 608 |
Mr = 281.81 | Dx = 1.139 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 14.0379 (13) Å | Cell parameters from 1846 reflections |
b = 10.3133 (5) Å | θ = 5.3–69.3° |
c = 11.4344 (7) Å | µ = 1.99 mm−1 |
β = 96.829 (7)° | T = 294 K |
V = 1643.7 (2) Å3 | Parallelepiped, colorless |
Z = 4 | 0.17 × 0.08 × 0.04 mm |
Agilent SuperNova diffractometer with an Atlas detector | 2938 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 1541 reflections with I > 2σ(I) |
Detector resolution: 10.4498 pixels mm-1 | Rint = 0.047 |
ω scans | θmax = 73.5°, θmin = 3.2° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −17→16 |
Tmin = 0.633, Tmax = 1.000 | k = −12→12 |
7563 measured reflections | l = −9→14 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.064 | w = 1/[σ2(Fo2) + (0.0959P)2 + 1.2724P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.245 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.30 e Å−3 |
2938 reflections | Δρmin = −0.42 e Å−3 |
175 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0033 (7) |
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. The single-crystal X-ray experiments were performed at room temperature. The data were collected using a SuperNova kappa diffractometer with Atlas CCD detector (Agilent Technologies, Santa Clara, CA, USA). For the integration of the collected data, the CrysAlis PRO software (version 1.171.38.41q, 2015; Rigaku Oxford Diffraction, Rigaku, Tokyo, Japan) was used. The structures were solved using direct methods with the SHELXS2013 software and the solutions were refined using SHELXL2018/3 program (Sheldrick, 2015). |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.63520 (11) | 0.06947 (12) | 0.15315 (10) | 0.0782 (5) | |
O1 | 0.2540 (3) | 0.8958 (4) | 0.3051 (3) | 0.0909 (13) | |
N1 | 0.3639 (3) | 0.7638 (3) | 0.1508 (3) | 0.0537 (9) | |
H1 | 0.351636 | 0.714736 | 0.220908 | 0.064* | |
C1 | 0.2412 (3) | 1.0750 (5) | 0.1768 (4) | 0.0602 (12) | |
C2 | 0.2739 (4) | 1.1340 (4) | 0.0811 (4) | 0.0658 (13) | |
H2 | 0.302599 | 1.084303 | 0.027163 | 0.079* | |
C3 | 0.2646 (4) | 1.2648 (5) | 0.0648 (5) | 0.0775 (15) | |
H3 | 0.288000 | 1.304273 | 0.000818 | 0.093* | |
C4 | 0.2206 (4) | 1.3378 (5) | 0.1434 (6) | 0.0854 (17) | |
H4 | 0.214854 | 1.427015 | 0.132957 | 0.103* | |
C5 | 0.1851 (5) | 1.2801 (6) | 0.2366 (5) | 0.0870 (17) | |
H5 | 0.153511 | 1.329683 | 0.287970 | 0.104* | |
C6 | 0.1961 (4) | 1.1491 (5) | 0.2548 (5) | 0.0741 (14) | |
H6 | 0.173231 | 1.110280 | 0.319351 | 0.089* | |
C7 | 0.2566 (3) | 0.9351 (4) | 0.2058 (4) | 0.0589 (12) | |
C8 | 0.2746 (3) | 0.8385 (4) | 0.1095 (4) | 0.0580 (11) | |
H8 | 0.282879 | 0.884964 | 0.036598 | 0.070* | |
C9 | 0.4504 (3) | 0.8451 (5) | 0.1838 (5) | 0.0719 (14) | |
H9A | 0.452305 | 0.917364 | 0.129811 | 0.086* | |
H9B | 0.451146 | 0.878614 | 0.263154 | 0.086* | |
C10 | 0.5327 (4) | 0.7561 (6) | 0.1758 (6) | 0.0900 (17) | |
H10A | 0.544935 | 0.703117 | 0.246123 | 0.108* | |
H10B | 0.590375 | 0.804048 | 0.164814 | 0.108* | |
C11 | 0.5005 (5) | 0.6751 (7) | 0.0708 (6) | 0.099 (2) | |
H11A | 0.528009 | 0.588945 | 0.080002 | 0.119* | |
H11B | 0.520335 | 0.714062 | 0.000404 | 0.119* | |
C12 | 0.3927 (4) | 0.6682 (5) | 0.0617 (4) | 0.0666 (13) | |
H12A | 0.372036 | 0.581353 | 0.079500 | 0.080* | |
H12B | 0.364199 | 0.691348 | −0.016952 | 0.080* | |
C13 | 0.1898 (4) | 0.7458 (5) | 0.0881 (4) | 0.0678 (13) | |
H13A | 0.203710 | 0.682122 | 0.030049 | 0.081* | |
H13B | 0.183685 | 0.699713 | 0.160821 | 0.081* | |
C14 | 0.0949 (4) | 0.8087 (7) | 0.0464 (5) | 0.0909 (18) | |
H14 | 0.083972 | 0.877490 | 0.102432 | 0.109* | |
C15 | 0.0937 (5) | 0.8701 (8) | −0.0740 (6) | 0.120 (3) | |
H15A | 0.135085 | 0.944462 | −0.068498 | 0.180* | |
H15B | 0.029448 | 0.896410 | −0.102272 | 0.180* | |
H15C | 0.115686 | 0.808340 | −0.127577 | 0.180* | |
C16 | 0.0147 (5) | 0.7099 (10) | 0.0476 (7) | 0.144 (3) | |
H16A | 0.028265 | 0.635831 | 0.001474 | 0.215* | |
H16B | −0.044905 | 0.748144 | 0.014863 | 0.215* | |
H16C | 0.010124 | 0.683291 | 0.127182 | 0.215* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1122 (12) | 0.0652 (7) | 0.0596 (7) | −0.0108 (7) | 0.0204 (7) | −0.0078 (5) |
O1 | 0.137 (4) | 0.085 (2) | 0.053 (2) | 0.022 (2) | 0.022 (2) | 0.0133 (18) |
N1 | 0.057 (2) | 0.058 (2) | 0.0457 (18) | −0.0032 (17) | 0.0056 (16) | −0.0022 (15) |
C1 | 0.060 (3) | 0.069 (3) | 0.049 (2) | 0.001 (2) | −0.002 (2) | −0.005 (2) |
C2 | 0.082 (4) | 0.055 (3) | 0.060 (3) | 0.005 (2) | 0.006 (2) | −0.002 (2) |
C3 | 0.081 (4) | 0.070 (3) | 0.079 (3) | −0.006 (3) | −0.001 (3) | 0.001 (3) |
C4 | 0.093 (4) | 0.057 (3) | 0.102 (4) | −0.004 (3) | −0.009 (3) | −0.009 (3) |
C5 | 0.100 (5) | 0.074 (4) | 0.087 (4) | 0.004 (3) | 0.013 (3) | −0.020 (3) |
C6 | 0.091 (4) | 0.066 (3) | 0.066 (3) | −0.002 (3) | 0.011 (3) | −0.012 (2) |
C7 | 0.072 (3) | 0.054 (2) | 0.051 (2) | 0.005 (2) | 0.007 (2) | 0.003 (2) |
C8 | 0.057 (3) | 0.061 (2) | 0.055 (2) | 0.004 (2) | 0.000 (2) | 0.006 (2) |
C9 | 0.057 (3) | 0.068 (3) | 0.088 (4) | −0.002 (2) | −0.003 (3) | −0.008 (3) |
C10 | 0.059 (4) | 0.090 (4) | 0.118 (5) | 0.004 (3) | −0.002 (3) | 0.000 (4) |
C11 | 0.079 (4) | 0.119 (5) | 0.100 (4) | 0.007 (4) | 0.016 (3) | −0.021 (4) |
C12 | 0.078 (4) | 0.067 (3) | 0.055 (3) | 0.001 (3) | 0.008 (2) | −0.009 (2) |
C13 | 0.061 (3) | 0.078 (3) | 0.063 (3) | −0.001 (3) | 0.005 (2) | −0.005 (2) |
C14 | 0.062 (4) | 0.121 (5) | 0.088 (4) | 0.007 (4) | 0.000 (3) | −0.015 (4) |
C15 | 0.091 (5) | 0.152 (7) | 0.109 (5) | 0.020 (5) | −0.022 (4) | 0.014 (5) |
C16 | 0.073 (5) | 0.219 (10) | 0.138 (7) | −0.034 (6) | 0.008 (4) | 0.001 (6) |
O1—C7 | 1.210 (5) | C9—H9B | 0.9700 |
N1—C9 | 1.487 (6) | C10—C11 | 1.488 (8) |
N1—C8 | 1.499 (5) | C10—H10A | 0.9700 |
N1—C12 | 1.507 (5) | C10—H10B | 0.9700 |
N1—H1 | 0.9800 | C11—C12 | 1.506 (8) |
C1—C2 | 1.378 (6) | C11—H11A | 0.9700 |
C1—C6 | 1.383 (7) | C11—H11B | 0.9700 |
C1—C7 | 1.491 (6) | C12—H12A | 0.9700 |
C2—C3 | 1.366 (7) | C12—H12B | 0.9700 |
C2—H2 | 0.9300 | C13—C14 | 1.507 (7) |
C3—C4 | 1.374 (8) | C13—H13A | 0.9700 |
C3—H3 | 0.9300 | C13—H13B | 0.9700 |
C4—C5 | 1.366 (8) | C14—C15 | 1.514 (8) |
C4—H4 | 0.9300 | C14—C16 | 1.520 (10) |
C5—C6 | 1.373 (7) | C14—H14 | 0.9800 |
C5—H5 | 0.9300 | C15—H15A | 0.9600 |
C6—H6 | 0.9300 | C15—H15B | 0.9600 |
C7—C8 | 1.528 (6) | C15—H15C | 0.9600 |
C8—C13 | 1.524 (7) | C16—H16A | 0.9600 |
C8—H8 | 0.9800 | C16—H16B | 0.9600 |
C9—C10 | 1.487 (7) | C16—H16C | 0.9600 |
C9—H9A | 0.9700 | ||
C9—N1—C8 | 114.7 (4) | C11—C10—H10A | 111.1 |
C9—N1—C12 | 105.3 (4) | C9—C10—H10B | 111.1 |
C8—N1—C12 | 113.8 (3) | C11—C10—H10B | 111.1 |
C9—N1—H1 | 107.6 | H10A—C10—H10B | 109.0 |
C8—N1—H1 | 107.6 | C10—C11—C12 | 106.8 (5) |
C12—N1—H1 | 107.6 | C10—C11—H11A | 110.4 |
C2—C1—C6 | 119.3 (5) | C12—C11—H11A | 110.4 |
C2—C1—C7 | 123.4 (4) | C10—C11—H11B | 110.4 |
C6—C1—C7 | 117.2 (4) | C12—C11—H11B | 110.4 |
C3—C2—C1 | 120.6 (5) | H11A—C11—H11B | 108.6 |
C3—C2—H2 | 119.7 | C11—C12—N1 | 105.7 (4) |
C1—C2—H2 | 119.7 | C11—C12—H12A | 110.6 |
C2—C3—C4 | 119.6 (6) | N1—C12—H12A | 110.6 |
C2—C3—H3 | 120.2 | C11—C12—H12B | 110.6 |
C4—C3—H3 | 120.2 | N1—C12—H12B | 110.6 |
C5—C4—C3 | 120.4 (5) | H12A—C12—H12B | 108.7 |
C5—C4—H4 | 119.8 | C14—C13—C8 | 115.1 (5) |
C3—C4—H4 | 119.8 | C14—C13—H13A | 108.5 |
C4—C5—C6 | 120.1 (6) | C8—C13—H13A | 108.5 |
C4—C5—H5 | 119.9 | C14—C13—H13B | 108.5 |
C6—C5—H5 | 119.9 | C8—C13—H13B | 108.5 |
C5—C6—C1 | 119.9 (5) | H13A—C13—H13B | 107.5 |
C5—C6—H6 | 120.1 | C13—C14—C15 | 112.5 (5) |
C1—C6—H6 | 120.1 | C13—C14—C16 | 109.6 (6) |
O1—C7—C1 | 120.8 (4) | C15—C14—C16 | 111.1 (6) |
O1—C7—C8 | 118.9 (4) | C13—C14—H14 | 107.8 |
C1—C7—C8 | 120.2 (4) | C15—C14—H14 | 107.8 |
N1—C8—C13 | 109.7 (4) | C16—C14—H14 | 107.8 |
N1—C8—C7 | 108.1 (3) | C14—C15—H15A | 109.5 |
C13—C8—C7 | 109.3 (4) | C14—C15—H15B | 109.5 |
N1—C8—H8 | 109.9 | H15A—C15—H15B | 109.5 |
C13—C8—H8 | 109.9 | C14—C15—H15C | 109.5 |
C7—C8—H8 | 109.9 | H15A—C15—H15C | 109.5 |
C10—C9—N1 | 104.7 (4) | H15B—C15—H15C | 109.5 |
C10—C9—H9A | 110.8 | C14—C16—H16A | 109.5 |
N1—C9—H9A | 110.8 | C14—C16—H16B | 109.5 |
C10—C9—H9B | 110.8 | H16A—C16—H16B | 109.5 |
N1—C9—H9B | 110.8 | C14—C16—H16C | 109.5 |
H9A—C9—H9B | 108.9 | H16A—C16—H16C | 109.5 |
C9—C10—C11 | 103.4 (5) | H16B—C16—H16C | 109.5 |
C9—C10—H10A | 111.1 | ||
C6—C1—C2—C3 | 1.9 (7) | O1—C7—C8—N1 | −52.9 (6) |
C7—C1—C2—C3 | −174.5 (5) | C1—C7—C8—N1 | 127.9 (4) |
C1—C2—C3—C4 | −1.3 (8) | O1—C7—C8—C13 | 66.5 (6) |
C2—C3—C4—C5 | −0.8 (8) | C1—C7—C8—C13 | −112.8 (5) |
C3—C4—C5—C6 | 2.1 (9) | C8—N1—C9—C10 | −158.7 (4) |
C4—C5—C6—C1 | −1.5 (9) | C12—N1—C9—C10 | −32.7 (5) |
C2—C1—C6—C5 | −0.5 (8) | N1—C9—C10—C11 | 38.1 (6) |
C7—C1—C6—C5 | 176.1 (5) | C9—C10—C11—C12 | −28.9 (7) |
C2—C1—C7—O1 | 157.2 (5) | C10—C11—C12—N1 | 9.0 (6) |
C6—C1—C7—O1 | −19.3 (7) | C9—N1—C12—C11 | 14.5 (5) |
C2—C1—C7—C8 | −23.6 (7) | C8—N1—C12—C11 | 140.9 (5) |
C6—C1—C7—C8 | 160.0 (4) | N1—C8—C13—C14 | 179.8 (4) |
C9—N1—C8—C13 | −175.4 (4) | C7—C8—C13—C14 | 61.4 (5) |
C12—N1—C8—C13 | 63.3 (5) | C8—C13—C14—C15 | 64.9 (7) |
C9—N1—C8—C7 | −56.3 (5) | C8—C13—C14—C16 | −170.9 (5) |
C12—N1—C8—C7 | −177.6 (4) |
C13H20NO+·Cl− | F(000) = 520 |
Mr = 241.75 | Dx = 1.140 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 7.1747 (2) Å | Cell parameters from 6458 reflections |
b = 7.8832 (2) Å | θ = 5.8–73.6° |
c = 24.9469 (6) Å | µ = 2.24 mm−1 |
β = 93.765 (2)° | T = 294 K |
V = 1407.94 (6) Å3 | Polyhedron, colorless |
Z = 4 | 0.38 × 0.33 × 0.08 mm |
Agilent SuperNova diffractometer with an Atlas detector | 2799 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 2694 reflections with I > 2σ(I) |
Detector resolution: 10.4498 pixels mm-1 | Rint = 0.016 |
ω scans | θmax = 73.5°, θmin = 3.6° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −8→6 |
Tmin = 0.600, Tmax = 1.000 | k = −8→9 |
9319 measured reflections | l = −29→30 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.128 | w = 1/[σ2(Fo2) + (0.0731P)2 + 0.3144P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
2799 reflections | Δρmax = 0.41 e Å−3 |
148 parameters | Δρmin = −0.26 e Å−3 |
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. The single-crystal X-ray experiments were performed at room temperature. The data were collected using a SuperNova kappa diffractometer with Atlas CCD detector (Agilent Technologies, Santa Clara, CA, USA). For the integration of the collected data, the CrysAlis PRO software (version 1.171.38.41q, 2015; Rigaku Oxford Diffraction, Rigaku, Tokyo, Japan) was used. The structures were solved using direct methods with the SHELXS2013 software and the solutions were refined using SHELXL2018/3 program (Sheldrick, 2015). |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.98520 (5) | 0.13609 (5) | 0.23702 (2) | 0.05579 (17) | |
O1 | 0.63367 (17) | −0.12727 (16) | 0.14209 (5) | 0.0611 (3) | |
N1 | 0.56633 (17) | 0.01840 (16) | 0.23441 (5) | 0.0485 (3) | |
H14A | 0.576783 | −0.091220 | 0.242590 | 0.058* | |
H14B | 0.675937 | 0.052917 | 0.223654 | 0.058* | |
C1 | 0.3264 (2) | −0.12105 (19) | 0.10155 (6) | 0.0495 (4) | |
C2 | 0.1371 (3) | −0.1186 (2) | 0.11019 (7) | 0.0587 (4) | |
H2 | 0.097612 | −0.082260 | 0.143057 | 0.070* | |
C3 | 0.0070 (3) | −0.1699 (3) | 0.07003 (8) | 0.0685 (5) | |
H3 | −0.119017 | −0.170254 | 0.076715 | 0.082* | |
C4 | 0.0597 (3) | −0.2205 (2) | 0.02051 (8) | 0.0670 (5) | |
C5 | 0.2473 (3) | −0.2187 (3) | 0.01155 (7) | 0.0743 (6) | |
H5 | 0.285158 | −0.249441 | −0.022041 | 0.089* | |
C6 | 0.3809 (3) | −0.1719 (3) | 0.05155 (7) | 0.0646 (5) | |
H6 | 0.506895 | −0.174461 | 0.044910 | 0.077* | |
C7 | 0.4736 (2) | −0.07816 (19) | 0.14386 (6) | 0.0473 (3) | |
C8 | 0.4223 (2) | 0.03854 (19) | 0.18908 (6) | 0.0476 (3) | |
H8 | 0.301161 | 0.003000 | 0.201248 | 0.057* | |
C9 | 0.5251 (3) | 0.1140 (3) | 0.28359 (8) | 0.0663 (5) | |
H9A | 0.531281 | 0.233577 | 0.276579 | 0.099* | |
H9B | 0.615171 | 0.084950 | 0.312274 | 0.099* | |
H9C | 0.402158 | 0.085362 | 0.293691 | 0.099* | |
C10 | 0.4045 (3) | 0.2197 (2) | 0.16777 (7) | 0.0600 (4) | |
H10A | 0.294877 | 0.226186 | 0.142936 | 0.072* | |
H10B | 0.383968 | 0.294841 | 0.197619 | 0.072* | |
C11 | 0.5703 (4) | 0.2836 (3) | 0.13969 (10) | 0.0822 (6) | |
H11A | 0.598673 | 0.204151 | 0.111682 | 0.099* | |
H11B | 0.677954 | 0.289277 | 0.165253 | 0.099* | |
C12 | 0.5352 (5) | 0.4574 (3) | 0.11506 (11) | 0.0999 (9) | |
H12A | 0.437293 | 0.449836 | 0.087018 | 0.150* | |
H12B | 0.647292 | 0.497751 | 0.100354 | 0.150* | |
H12C | 0.498711 | 0.534689 | 0.142209 | 0.150* | |
C13 | −0.0843 (4) | −0.2748 (3) | −0.02325 (10) | 0.0945 (8) | |
H13A | −0.159547 | −0.364419 | −0.010068 | 0.142* | |
H13B | −0.022123 | −0.314483 | −0.053783 | 0.142* | |
H13C | −0.162519 | −0.180013 | −0.033631 | 0.142* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0426 (2) | 0.0505 (3) | 0.0748 (3) | 0.00148 (14) | 0.00800 (18) | −0.01062 (16) |
O1 | 0.0526 (7) | 0.0611 (7) | 0.0700 (7) | 0.0078 (5) | 0.0063 (6) | −0.0106 (5) |
N1 | 0.0457 (7) | 0.0453 (7) | 0.0544 (7) | 0.0014 (5) | 0.0027 (5) | −0.0009 (5) |
C1 | 0.0562 (9) | 0.0417 (8) | 0.0508 (8) | 0.0015 (6) | 0.0044 (7) | 0.0011 (6) |
C2 | 0.0573 (10) | 0.0629 (10) | 0.0560 (9) | −0.0028 (7) | 0.0050 (7) | −0.0018 (7) |
C3 | 0.0606 (11) | 0.0742 (12) | 0.0696 (11) | −0.0063 (9) | −0.0039 (8) | −0.0022 (9) |
C4 | 0.0776 (12) | 0.0564 (10) | 0.0651 (10) | −0.0003 (9) | −0.0114 (9) | 0.0000 (8) |
C5 | 0.0920 (15) | 0.0789 (13) | 0.0515 (9) | 0.0068 (11) | 0.0012 (9) | −0.0102 (9) |
C6 | 0.0663 (11) | 0.0706 (11) | 0.0574 (9) | 0.0054 (9) | 0.0088 (8) | −0.0063 (8) |
C7 | 0.0492 (8) | 0.0392 (7) | 0.0540 (8) | 0.0023 (6) | 0.0074 (6) | 0.0021 (6) |
C8 | 0.0456 (8) | 0.0449 (8) | 0.0523 (8) | 0.0032 (6) | 0.0028 (6) | −0.0017 (6) |
C9 | 0.0643 (11) | 0.0773 (13) | 0.0569 (10) | 0.0032 (9) | 0.0009 (8) | −0.0151 (9) |
C10 | 0.0713 (11) | 0.0439 (8) | 0.0638 (10) | 0.0100 (7) | −0.0034 (8) | −0.0024 (7) |
C11 | 0.1015 (17) | 0.0564 (11) | 0.0892 (14) | −0.0018 (11) | 0.0090 (12) | 0.0174 (10) |
C12 | 0.161 (3) | 0.0510 (11) | 0.0849 (15) | −0.0130 (14) | −0.0136 (16) | 0.0133 (11) |
C13 | 0.113 (2) | 0.0822 (15) | 0.0828 (14) | −0.0043 (14) | −0.0348 (14) | −0.0086 (12) |
O1—C7 | 1.2158 (19) | C8—C10 | 1.527 (2) |
N1—C9 | 1.486 (2) | C8—H8 | 0.9800 |
N1—C8 | 1.4894 (19) | C9—H9A | 0.9600 |
N1—H14A | 0.8900 | C9—H9B | 0.9600 |
N1—H14B | 0.8900 | C9—H9C | 0.9600 |
C1—C2 | 1.390 (2) | C10—C11 | 1.506 (3) |
C1—C6 | 1.390 (2) | C10—H10A | 0.9700 |
C1—C7 | 1.482 (2) | C10—H10B | 0.9700 |
C2—C3 | 1.384 (3) | C11—C12 | 1.516 (3) |
C2—H2 | 0.9300 | C11—H11A | 0.9700 |
C3—C4 | 1.375 (3) | C11—H11B | 0.9700 |
C3—H3 | 0.9300 | C12—H12A | 0.9600 |
C4—C5 | 1.379 (3) | C12—H12B | 0.9600 |
C4—C13 | 1.515 (3) | C12—H12C | 0.9600 |
C5—C6 | 1.387 (3) | C13—H13A | 0.9600 |
C5—H5 | 0.9300 | C13—H13B | 0.9600 |
C6—H6 | 0.9300 | C13—H13C | 0.9600 |
C7—C8 | 1.520 (2) | ||
C9—N1—C8 | 114.00 (12) | C10—C8—H8 | 108.6 |
C9—N1—H14A | 108.8 | N1—C9—H9A | 109.5 |
C8—N1—H14A | 108.8 | N1—C9—H9B | 109.5 |
C9—N1—H14B | 108.8 | H9A—C9—H9B | 109.5 |
C8—N1—H14B | 108.8 | N1—C9—H9C | 109.5 |
H14A—N1—H14B | 107.6 | H9A—C9—H9C | 109.5 |
C2—C1—C6 | 118.58 (16) | H9B—C9—H9C | 109.5 |
C2—C1—C7 | 122.97 (15) | C11—C10—C8 | 115.10 (15) |
C6—C1—C7 | 118.41 (15) | C11—C10—H10A | 108.5 |
C3—C2—C1 | 120.22 (18) | C8—C10—H10A | 108.5 |
C3—C2—H2 | 119.9 | C11—C10—H10B | 108.5 |
C1—C2—H2 | 119.9 | C8—C10—H10B | 108.5 |
C4—C3—C2 | 121.55 (19) | H10A—C10—H10B | 107.5 |
C4—C3—H3 | 119.2 | C10—C11—C12 | 112.1 (2) |
C2—C3—H3 | 119.2 | C10—C11—H11A | 109.2 |
C3—C4—C5 | 118.13 (18) | C12—C11—H11A | 109.2 |
C3—C4—C13 | 121.0 (2) | C10—C11—H11B | 109.2 |
C5—C4—C13 | 120.9 (2) | C12—C11—H11B | 109.2 |
C4—C5—C6 | 121.46 (18) | H11A—C11—H11B | 107.9 |
C4—C5—H5 | 119.3 | C11—C12—H12A | 109.5 |
C6—C5—H5 | 119.3 | C11—C12—H12B | 109.5 |
C5—C6—C1 | 120.03 (18) | H12A—C12—H12B | 109.5 |
C5—C6—H6 | 120.0 | C11—C12—H12C | 109.5 |
C1—C6—H6 | 120.0 | H12A—C12—H12C | 109.5 |
O1—C7—C1 | 122.14 (15) | H12B—C12—H12C | 109.5 |
O1—C7—C8 | 119.68 (14) | C4—C13—H13A | 109.5 |
C1—C7—C8 | 118.11 (13) | C4—C13—H13B | 109.5 |
N1—C8—C7 | 108.02 (12) | H13A—C13—H13B | 109.5 |
N1—C8—C10 | 113.71 (13) | C4—C13—H13C | 109.5 |
C7—C8—C10 | 109.07 (13) | H13A—C13—H13C | 109.5 |
N1—C8—H8 | 108.6 | H13B—C13—H13C | 109.5 |
C7—C8—H8 | 108.6 | ||
C6—C1—C2—C3 | 1.6 (3) | C2—C1—C7—C8 | −25.7 (2) |
C7—C1—C2—C3 | −176.03 (16) | C6—C1—C7—C8 | 156.66 (15) |
C1—C2—C3—C4 | −1.6 (3) | C9—N1—C8—C7 | −174.85 (14) |
C2—C3—C4—C5 | −0.1 (3) | C9—N1—C8—C10 | 63.95 (18) |
C2—C3—C4—C13 | −179.40 (19) | O1—C7—C8—N1 | −21.3 (2) |
C3—C4—C5—C6 | 1.8 (3) | C1—C7—C8—N1 | 161.81 (13) |
C13—C4—C5—C6 | −178.9 (2) | O1—C7—C8—C10 | 102.75 (17) |
C4—C5—C6—C1 | −1.7 (3) | C1—C7—C8—C10 | −74.14 (17) |
C2—C1—C6—C5 | 0.0 (3) | N1—C8—C10—C11 | 67.9 (2) |
C7—C1—C6—C5 | 177.76 (17) | C7—C8—C10—C11 | −52.7 (2) |
C2—C1—C7—O1 | 157.51 (16) | C8—C10—C11—C12 | 174.53 (18) |
C6—C1—C7—O1 | −20.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A | |
4-MPHP (1) | C8—H8···Cl1i | 0.98 | 2.59 | 3.522 (2) | 160 |
N1—H1···Cl1 | 0.98 | 2.15 | 3.048 (2) | 152 | |
α-PiHP (2) | N1—H1···Cl1ii | 0.98 | 2.07 | 3.006 (4) | 159 |
C2—H2···Cl1iii | 0.93 | 2.82 | 3.744 (5) | 172 | |
C8—H8···Cl1iii | 0.98 | 2.62 | 3.525 (5) | 154 | |
C10—H10B···Cl1iv | 0.97 | 2.82 | 3.560 (6) | 134 | |
C12—H12B···Cl1iii | 0.97 | 2.92 | 3.645 (5) | 133 | |
C12—H12B···O1v | 0.97 | 2.57 | 3.388 (6) | 142 | |
4-MPD (3) | N1—H14A···Cl1vi | 0.89 | 2.26 | 3.1245 (13) | 164 |
N1—H14B···Cl1 | 0.89 | 2.32 | 3.1418 (13) | 154 | |
C8—H8···Cl1vii | 0.98 | 2.70 | 3.5140 (16) | 141 |
Symmetry codes: (i) x, y+1, z; (ii) -x+1, y+1/2, -z+1/2; (iii) -x+1, -y+1, -z; (iv) x, y+1, z; (v) x, -y+3/2, z-1/2; (vi) -x+3/2, y-1/2, -z+1/2; (vii) x-1, y, z. |
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