In the crystal structure of the title compound, C
17H
28NO
+·ClO
4−, the
N-protonated piperidine ring is present in the normal chair conformation. The perchlorate anions link the cations, through intermolecular N—H
O and O—H
O hydrogen bonds, forming a chain-like structure.
Supporting information
CCDC reference: 221695
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.050
- wR factor = 0.130
- Data-to-parameter ratio = 11.8
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level A:
DIFF_019 Alert A _diffrn_standards_number is missing
Number of standards used in measurement.
DIFF_020 Alert A _diffrn_standards_interval_count and
_diffrn_standards_interval_time are missing. Number of measurements
between standards or time (min) between standards.
DIFF_022 Alert A _diffrn_standards_decay_% is missing
Percentage decrease in standards intensity.
3 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
0 Alert Level C = Please check
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 1998); software used to prepare material for publication: SHELXL97.
2-
tert-Butyl-4-methyl-6-(piperidyl-
N-methyl)phenol perchlorate
top
Crystal data top
C17H28NO+·ClO4− | F(000) = 776 |
Mr = 361.85 | Dx = 1.264 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.639 (5) Å | Cell parameters from 5481 reflections |
b = 10.390 (4) Å | θ = 2.4–25.0° |
c = 16.466 (6) Å | µ = 0.23 mm−1 |
β = 107.297 (7)° | T = 293 K |
V = 1901.1 (13) Å3 | Prism, colorless |
Z = 4 | 0.20 × 0.15 × 0.10 mm |
Data collection top
Bruker SMART 1000 diffractometer | 1555 reflections with I > 2σ(I) |
ω scans | Rint = 0.041 |
Absorption correction: multi-scan SAINT (Bruker 1998) and SADABS (Sheldrick, 1997) | θmax = 25.0° |
Tmin = 0.956, Tmax = 0.978 | h = −7→12 |
5523 measured reflections | k = −11→11 |
3256 independent reflections | l = −18→13 |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.050 | w = 1/[σ2(Fo2) + (0.06P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.130 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.27 e Å−3 |
2656 reflections | Δρmin = −0.22 e Å−3 |
226 parameters | |
Special details top
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. Full-MATRIX |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.7726 (2) | 0.9106 (2) | 0.23789 (14) | 0.0570 (7) | |
H1 | 0.8231 | 0.8640 | 0.2272 | 0.086* | |
N1 | 1.0332 (2) | 0.7523 (2) | 0.40337 (16) | 0.0398 (7) | |
H2 | 1.0293 | 0.7381 | 0.4570 | 0.048* | |
C1 | 1.1383 (3) | 0.6783 (4) | 0.3938 (2) | 0.0563 (10) | |
H1A | 1.1430 | 0.6888 | 0.3364 | 0.068* | |
H1B | 1.1269 | 0.5875 | 0.4028 | 0.068* | |
C2 | 1.2550 (3) | 0.7229 (4) | 0.4564 (3) | 0.0729 (13) | |
H2A | 1.3217 | 0.6758 | 0.4468 | 0.087* | |
H2B | 1.2535 | 0.7051 | 0.5139 | 0.087* | |
C3 | 1.2731 (3) | 0.8660 (5) | 0.4466 (3) | 0.0763 (13) | |
H3A | 1.3460 | 0.8940 | 0.4891 | 0.092* | |
H3B | 1.2819 | 0.8831 | 0.3909 | 0.092* | |
C4 | 1.1664 (3) | 0.9399 (4) | 0.4572 (3) | 0.0739 (13) | |
H4A | 1.1622 | 0.9285 | 0.5147 | 0.089* | |
H4B | 1.1772 | 1.0310 | 0.4486 | 0.089* | |
C5 | 1.0502 (3) | 0.8948 (3) | 0.3946 (2) | 0.0532 (10) | |
H5A | 0.9832 | 0.9408 | 0.4046 | 0.064* | |
H5B | 1.0513 | 0.9137 | 0.3372 | 0.064* | |
C6 | 0.9174 (3) | 0.7042 (3) | 0.3425 (2) | 0.0420 (9) | |
H6A | 0.9133 | 0.6115 | 0.3483 | 0.050* | |
H6B | 0.9176 | 0.7224 | 0.2848 | 0.050* | |
C7 | 0.8076 (3) | 0.7640 (3) | 0.3571 (2) | 0.0380 (8) | |
C8 | 0.7403 (3) | 0.8604 (3) | 0.3054 (2) | 0.0377 (8) | |
C9 | 0.6360 (3) | 0.9113 (3) | 0.3199 (2) | 0.0375 (8) | |
C14 | 0.5591 (3) | 1.0149 (3) | 0.2621 (2) | 0.0452 (9) | |
C16 | 0.6341 (3) | 1.1380 (3) | 0.2647 (3) | 0.0694 (12) | |
H16A | 0.6633 | 1.1686 | 0.3222 | 0.104* | |
H16B | 0.5848 | 1.2029 | 0.2297 | 0.104* | |
H16C | 0.7010 | 1.1190 | 0.2439 | 0.104* | |
C15 | 0.5108 (3) | 0.9650 (4) | 0.1704 (2) | 0.0677 (12) | |
H15A | 0.4636 | 0.8889 | 0.1695 | 0.102* | |
H15B | 0.5770 | 0.9449 | 0.1491 | 0.102* | |
H15C | 0.4615 | 1.0300 | 0.1353 | 0.102* | |
C17 | 0.4494 (3) | 1.0524 (4) | 0.2893 (3) | 0.0722 (12) | |
H17B | 0.4004 | 0.9777 | 0.2883 | 0.108* | |
H17C | 0.4034 | 1.1160 | 0.2510 | 0.108* | |
H17A | 0.4752 | 1.0870 | 0.3459 | 0.108* | |
C10 | 0.6062 (3) | 0.8625 (3) | 0.3888 (2) | 0.0440 (9) | |
H10A | 0.5385 | 0.8959 | 0.4003 | 0.053* | |
C11 | 0.6702 (3) | 0.7670 (4) | 0.4421 (2) | 0.0465 (9) | |
C13 | 0.6316 (3) | 0.7175 (4) | 0.5163 (2) | 0.0714 (13) | |
H13C | 0.6872 | 0.6527 | 0.5460 | 0.107* | |
H13B | 0.5525 | 0.6811 | 0.4958 | 0.107* | |
H13A | 0.6308 | 0.7873 | 0.5543 | 0.107* | |
C12 | 0.7698 (3) | 0.7183 (3) | 0.4247 (2) | 0.0452 (9) | |
H12A | 0.8134 | 0.6530 | 0.4589 | 0.054* | |
Cl1 | 0.03997 (9) | 0.81452 (10) | 0.13528 (7) | 0.0579 (4) | |
O2 | 0.1349 (3) | 0.8529 (3) | 0.20582 (18) | 0.1145 (13) | |
O3 | 0.0506 (4) | 0.6872 (3) | 0.1139 (3) | 0.1540 (17) | |
O4 | 0.0424 (3) | 0.8887 (3) | 0.06404 (17) | 0.1029 (11) | |
O5 | −0.0700 (3) | 0.8373 (5) | 0.1497 (2) | 0.1450 (17) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0643 (16) | 0.0642 (17) | 0.0541 (16) | 0.0217 (14) | 0.0353 (14) | 0.0185 (13) |
N1 | 0.0359 (17) | 0.0451 (17) | 0.0393 (17) | 0.0042 (14) | 0.0127 (14) | 0.0053 (14) |
C1 | 0.046 (2) | 0.052 (2) | 0.074 (3) | 0.015 (2) | 0.024 (2) | 0.006 (2) |
C2 | 0.038 (3) | 0.100 (4) | 0.078 (3) | 0.016 (2) | 0.013 (2) | 0.001 (3) |
C3 | 0.039 (2) | 0.108 (4) | 0.079 (3) | −0.014 (3) | 0.014 (2) | −0.011 (3) |
C4 | 0.054 (3) | 0.069 (3) | 0.095 (3) | −0.015 (2) | 0.017 (2) | −0.023 (3) |
C5 | 0.047 (2) | 0.044 (2) | 0.069 (3) | 0.0003 (19) | 0.018 (2) | −0.005 (2) |
C6 | 0.040 (2) | 0.035 (2) | 0.047 (2) | 0.0013 (17) | 0.0061 (17) | −0.0032 (17) |
C7 | 0.037 (2) | 0.037 (2) | 0.040 (2) | −0.0013 (17) | 0.0110 (18) | −0.0029 (17) |
C8 | 0.040 (2) | 0.040 (2) | 0.035 (2) | −0.0009 (17) | 0.0147 (18) | −0.0017 (17) |
C9 | 0.035 (2) | 0.040 (2) | 0.037 (2) | −0.0028 (17) | 0.0105 (17) | −0.0038 (17) |
C14 | 0.041 (2) | 0.045 (2) | 0.048 (2) | 0.0053 (18) | 0.0114 (18) | 0.0015 (18) |
C16 | 0.066 (3) | 0.041 (2) | 0.100 (3) | 0.005 (2) | 0.022 (2) | 0.010 (2) |
C15 | 0.071 (3) | 0.068 (3) | 0.055 (3) | 0.012 (2) | 0.005 (2) | 0.010 (2) |
C17 | 0.062 (3) | 0.074 (3) | 0.084 (3) | 0.026 (2) | 0.025 (2) | 0.009 (2) |
C10 | 0.033 (2) | 0.055 (2) | 0.046 (2) | −0.0026 (18) | 0.0144 (18) | −0.0071 (19) |
C11 | 0.039 (2) | 0.058 (2) | 0.040 (2) | −0.0082 (19) | 0.0094 (19) | 0.0053 (19) |
C13 | 0.060 (3) | 0.103 (4) | 0.055 (3) | −0.005 (2) | 0.022 (2) | 0.017 (2) |
C12 | 0.040 (2) | 0.048 (2) | 0.042 (2) | −0.0039 (18) | 0.0040 (18) | 0.0094 (18) |
Cl1 | 0.0667 (7) | 0.0591 (7) | 0.0526 (7) | 0.0129 (6) | 0.0248 (6) | 0.0008 (5) |
O2 | 0.125 (3) | 0.134 (3) | 0.055 (2) | 0.006 (2) | −0.018 (2) | −0.011 (2) |
O3 | 0.132 (3) | 0.053 (2) | 0.264 (5) | 0.001 (2) | 0.039 (3) | −0.035 (3) |
O4 | 0.140 (3) | 0.119 (3) | 0.0518 (18) | −0.035 (2) | 0.0328 (18) | 0.0072 (18) |
O5 | 0.105 (3) | 0.252 (5) | 0.106 (3) | 0.072 (3) | 0.075 (2) | 0.037 (3) |
Geometric parameters (Å, º) top
O1—C8 | 1.378 (4) | C9—C10 | 1.377 (4) |
O1—H1 | 0.8200 | C9—C14 | 1.536 (4) |
N1—C1 | 1.492 (4) | C14—C17 | 1.524 (5) |
N1—C6 | 1.506 (4) | C14—C15 | 1.537 (4) |
N1—C5 | 1.506 (4) | C14—C16 | 1.542 (5) |
N1—H2 | 0.9100 | C16—H16A | 0.9600 |
C1—C2 | 1.512 (5) | C16—H16B | 0.9600 |
C1—H1A | 0.9700 | C16—H16C | 0.9600 |
C1—H1B | 0.9700 | C15—H15A | 0.9600 |
C2—C3 | 1.516 (5) | C15—H15B | 0.9600 |
C2—H2A | 0.9700 | C15—H15C | 0.9600 |
C2—H2B | 0.9700 | C17—H17B | 0.9600 |
C3—C4 | 1.513 (5) | C17—H17C | 0.9600 |
C3—H3A | 0.9700 | C17—H17A | 0.9600 |
C3—H3B | 0.9700 | C10—C11 | 1.387 (4) |
C4—C5 | 1.511 (4) | C10—H10A | 0.9300 |
C4—H4A | 0.9700 | C11—C12 | 1.371 (5) |
C4—H4B | 0.9700 | C11—C13 | 1.512 (5) |
C5—H5A | 0.9700 | C13—H13C | 0.9600 |
C5—H5B | 0.9700 | C13—H13B | 0.9600 |
C6—C7 | 1.503 (4) | C13—H13A | 0.9600 |
C6—H6A | 0.9700 | C12—H12A | 0.9300 |
C6—H6B | 0.9700 | Cl1—O3 | 1.384 (3) |
C7—C8 | 1.395 (4) | Cl1—O5 | 1.390 (3) |
C7—C12 | 1.396 (4) | Cl1—O2 | 1.402 (3) |
C8—C9 | 1.408 (4) | Cl1—O4 | 1.411 (3) |
| | | |
C8—O1—H1 | 109.5 | C10—C9—C8 | 116.3 (3) |
C1—N1—C6 | 111.0 (3) | C10—C9—C14 | 121.6 (3) |
C1—N1—C5 | 111.2 (3) | C8—C9—C14 | 122.1 (3) |
C6—N1—C5 | 112.3 (2) | C17—C14—C9 | 112.4 (3) |
C1—N1—H2 | 107.4 | C17—C14—C15 | 106.3 (3) |
C6—N1—H2 | 107.4 | C9—C14—C15 | 110.4 (3) |
C5—N1—H2 | 107.4 | C17—C14—C16 | 107.3 (3) |
N1—C1—C2 | 111.6 (3) | C9—C14—C16 | 110.1 (3) |
N1—C1—H1A | 109.3 | C15—C14—C16 | 110.2 (3) |
C2—C1—H1A | 109.3 | C14—C16—H16A | 109.5 |
N1—C1—H1B | 109.3 | C14—C16—H16B | 109.5 |
C2—C1—H1B | 109.3 | H16A—C16—H16B | 109.5 |
H1A—C1—H1B | 108.0 | C14—C16—H16C | 109.5 |
C1—C2—C3 | 110.7 (3) | H16A—C16—H16C | 109.5 |
C1—C2—H2A | 109.5 | H16B—C16—H16C | 109.5 |
C3—C2—H2A | 109.5 | C14—C15—H15A | 109.5 |
C1—C2—H2B | 109.5 | C14—C15—H15B | 109.5 |
C3—C2—H2B | 109.5 | H15A—C15—H15B | 109.5 |
H2A—C2—H2B | 108.1 | C14—C15—H15C | 109.5 |
C4—C3—C2 | 109.9 (3) | H15A—C15—H15C | 109.5 |
C4—C3—H3A | 109.7 | H15B—C15—H15C | 109.5 |
C2—C3—H3A | 109.7 | C14—C17—H17B | 109.5 |
C4—C3—H3B | 109.7 | C14—C17—H17C | 109.5 |
C2—C3—H3B | 109.7 | H17B—C17—H17C | 109.5 |
H3A—C3—H3B | 108.2 | C14—C17—H17A | 109.5 |
C5—C4—C3 | 111.3 (3) | H17B—C17—H17A | 109.5 |
C5—C4—H4A | 109.4 | H17C—C17—H17A | 109.5 |
C3—C4—H4A | 109.4 | C9—C10—C11 | 124.4 (3) |
C5—C4—H4B | 109.4 | C9—C10—H10A | 117.8 |
C3—C4—H4B | 109.4 | C11—C10—H10A | 117.8 |
H4A—C4—H4B | 108.0 | C12—C11—C10 | 117.4 (3) |
N1—C5—C4 | 110.9 (3) | C12—C11—C13 | 121.1 (3) |
N1—C5—H5A | 109.5 | C10—C11—C13 | 121.5 (3) |
C4—C5—H5A | 109.5 | C11—C13—H13C | 109.5 |
N1—C5—H5B | 109.5 | C11—C13—H13B | 109.5 |
C4—C5—H5B | 109.5 | H13C—C13—H13B | 109.5 |
H5A—C5—H5B | 108.0 | C11—C13—H13A | 109.5 |
N1—C6—C7 | 113.0 (3) | H13C—C13—H13A | 109.5 |
N1—C6—H6A | 109.0 | H13B—C13—H13A | 109.5 |
C7—C6—H6A | 109.0 | C11—C12—C7 | 121.9 (3) |
N1—C6—H6B | 109.0 | C11—C12—H12A | 119.1 |
C7—C6—H6B | 109.0 | C7—C12—H12A | 119.1 |
H6A—C6—H6B | 107.8 | O3—Cl1—O5 | 111.3 (3) |
C8—C7—C12 | 118.5 (3) | O3—Cl1—O2 | 112.0 (2) |
C8—C7—C6 | 123.3 (3) | O5—Cl1—O2 | 110.4 (2) |
C12—C7—C6 | 118.1 (3) | O3—Cl1—O4 | 106.5 (3) |
O1—C8—C7 | 121.8 (3) | O5—Cl1—O4 | 107.3 (2) |
O1—C8—C9 | 116.8 (3) | O2—Cl1—O4 | 109.1 (2) |
C7—C8—C9 | 121.5 (3) | | |
| | | |
C6—N1—C1—C2 | −178.3 (3) | C7—C8—C9—C10 | 1.4 (5) |
C5—N1—C1—C2 | 55.9 (4) | O1—C8—C9—C14 | 1.8 (4) |
N1—C1—C2—C3 | −56.6 (4) | C7—C8—C9—C14 | −178.3 (3) |
C1—C2—C3—C4 | 56.4 (4) | C10—C9—C14—C17 | −1.1 (4) |
C2—C3—C4—C5 | −56.7 (5) | C8—C9—C14—C17 | 178.6 (3) |
C1—N1—C5—C4 | −55.5 (4) | C10—C9—C14—C15 | −119.6 (3) |
C6—N1—C5—C4 | 179.4 (3) | C8—C9—C14—C15 | 60.1 (4) |
C3—C4—C5—N1 | 56.4 (4) | C10—C9—C14—C16 | 118.5 (3) |
C1—N1—C6—C7 | 172.7 (3) | C8—C9—C14—C16 | −61.8 (4) |
C5—N1—C6—C7 | −62.1 (4) | C8—C9—C10—C11 | −1.3 (5) |
N1—C6—C7—C8 | 103.7 (4) | C14—C9—C10—C11 | 178.5 (3) |
N1—C6—C7—C12 | −77.9 (4) | C9—C10—C11—C12 | 0.0 (5) |
C12—C7—C8—O1 | 179.6 (3) | C9—C10—C11—C13 | −179.6 (3) |
C6—C7—C8—O1 | −2.0 (5) | C10—C11—C12—C7 | 1.2 (5) |
C12—C7—C8—C9 | −0.2 (5) | C13—C11—C12—C7 | −179.1 (3) |
C6—C7—C8—C9 | 178.2 (3) | C8—C7—C12—C11 | −1.1 (5) |
O1—C8—C9—C10 | −178.5 (3) | C6—C7—C12—C11 | −179.6 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O5i | 0.82 | 2.05 | 2.761 (4) | 145 |
N1—H2···O4ii | 0.91 | 2.17 | 2.998 (5) | 151 |
Symmetry codes: (i) x+1, y, z; (ii) x+1, −y+3/2, z+1/2. |