In the crystal structure of the title compound, C
17H
28NO
+·Cl
−, the
N-protonated piperidine ring adopts the normal chair conformation. Each chloride anion acts as an acceptor in N—H
Cl and O—H
Cl hydrogen bonds, resulting in an
R21(8) ring pattern. Intermolecular C—H
Cl and C—H
O interactions further extend these patterns to form a two-dimensional supramolecular network.
Supporting information
CCDC reference: 232140
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.105
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.840 1.000
Tmin' and Tmax expected: 0.928 0.958
RR' = 0.868
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.87
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12B .. CL1 = 2.91 Ang.
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.03
From the CIF: _reflns_number_total 3092
Count of symmetry unique reflns 1819
Completeness (_total/calc) 169.98%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1273
Fraction of Friedel pairs measured 0.700
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
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 in SHELXTL (Bruker, 1998).
2-
tert-Butyl-4-methyl-6-(1-piperidiniomethyl)phenol chloride
top
Crystal data top
C17H28NO+·Cl− | F(000) = 648 |
Mr = 297.85 | Dx = 1.124 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 827 reflections |
a = 5.882 (2) Å | θ = 3.3–22.8° |
b = 12.187 (5) Å | µ = 0.21 mm−1 |
c = 24.553 (10) Å | T = 293 K |
V = 1760.1 (12) Å3 | Block, colorless |
Z = 4 | 0.34 × 0.32 × 0.20 mm |
Data collection top
Bruker SMART 1000 diffractometer | 2288 reflections with I > 2σ(I) |
ω scans | Rint = 0.033 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 25.0°, θmin = 2.4° |
Tmin = 0.841, Tmax = 1.000 | h = −5→7 |
7868 measured reflections | k = −14→13 |
3092 independent reflections | l = −29→14 |
Refinement top
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0567P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.044 | (Δ/σ)max = 0.001 |
wR(F2) = 0.105 | Δρmax = 0.17 e Å−3 |
S = 1.02 | Δρmin = −0.16 e Å−3 |
3092 reflections | Absolute structure: Flack (1983); 1275 Friedel pairs |
186 parameters | Absolute structure parameter: −0.11 (8) |
H-atom parameters constrained | |
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 | |
Cl1 | 0.67538 (12) | 0.38671 (5) | 0.76206 (3) | 0.0619 (2) | |
N1 | 0.0416 (3) | 0.10464 (15) | 0.73289 (8) | 0.0427 (5) | |
H1 | 0.1204 | 0.0405 | 0.7311 | 0.051* | |
O1 | 0.1507 (3) | −0.04949 (14) | 0.62543 (7) | 0.0561 (5) | |
H1A | 0.1922 | −0.0712 | 0.6554 | 0.084* | |
C1 | 0.2624 (4) | 0.0475 (2) | 0.61293 (10) | 0.0451 (6) | |
C2 | 0.1876 (5) | 0.1429 (2) | 0.63841 (10) | 0.0501 (6) | |
C3 | 0.2985 (5) | 0.2407 (2) | 0.62721 (12) | 0.0632 (8) | |
H3 | 0.2494 | 0.3047 | 0.6441 | 0.076* | |
C4 | 0.4796 (5) | 0.2453 (2) | 0.59167 (12) | 0.0609 (8) | |
C5 | 0.5403 (5) | 0.1493 (2) | 0.56519 (11) | 0.0552 (7) | |
H5 | 0.6569 | 0.1524 | 0.5397 | 0.066* | |
C6 | 0.4373 (4) | 0.0489 (2) | 0.57453 (10) | 0.0437 (6) | |
C7 | −0.0151 (5) | 0.1392 (2) | 0.67555 (11) | 0.0559 (7) | |
H7A | −0.1259 | 0.0885 | 0.6606 | 0.067* | |
H7B | −0.0846 | 0.2114 | 0.6765 | 0.067* | |
C8 | 0.1879 (5) | 0.18707 (18) | 0.76109 (10) | 0.0498 (6) | |
H8A | 0.1092 | 0.2569 | 0.7627 | 0.060* | |
H8B | 0.3273 | 0.1974 | 0.7406 | 0.060* | |
C9 | 0.2442 (5) | 0.1498 (3) | 0.81782 (11) | 0.0677 (9) | |
H9A | 0.3374 | 0.2049 | 0.8356 | 0.081* | |
H9B | 0.3312 | 0.0823 | 0.8161 | 0.081* | |
C10 | 0.0319 (7) | 0.1310 (3) | 0.85084 (13) | 0.0844 (11) | |
H10A | 0.0720 | 0.1042 | 0.8868 | 0.101* | |
H10B | −0.0500 | 0.1996 | 0.8551 | 0.101* | |
C11 | −0.1158 (6) | 0.0486 (3) | 0.82230 (14) | 0.0780 (10) | |
H11A | −0.2560 | 0.0394 | 0.8426 | 0.094* | |
H11B | −0.0385 | −0.0217 | 0.8214 | 0.094* | |
C12 | −0.1715 (4) | 0.0839 (2) | 0.76430 (13) | 0.0592 (7) | |
H12A | −0.2594 | 0.0270 | 0.7465 | 0.071* | |
H12B | −0.2628 | 0.1502 | 0.7651 | 0.071* | |
C13 | 0.6082 (8) | 0.3504 (2) | 0.58199 (16) | 0.0943 (12) | |
H13A | 0.5045 | 0.4064 | 0.5701 | 0.141* | |
H13B | 0.7215 | 0.3387 | 0.5545 | 0.141* | |
H13C | 0.6804 | 0.3731 | 0.6152 | 0.141* | |
C14 | 0.5142 (5) | −0.0558 (2) | 0.54409 (11) | 0.0509 (7) | |
C15 | 0.6119 (5) | −0.1378 (2) | 0.58547 (12) | 0.0654 (8) | |
H15A | 0.6568 | −0.2037 | 0.5669 | 0.098* | |
H15B | 0.4983 | −0.1549 | 0.6122 | 0.098* | |
H15C | 0.7418 | −0.1060 | 0.6031 | 0.098* | |
C16 | 0.3126 (5) | −0.1083 (2) | 0.51392 (11) | 0.0664 (8) | |
H16A | 0.2502 | −0.0564 | 0.4886 | 0.100* | |
H16B | 0.1979 | −0.1291 | 0.5398 | 0.100* | |
H16C | 0.3638 | −0.1721 | 0.4946 | 0.100* | |
C17 | 0.6975 (6) | −0.0308 (3) | 0.50233 (13) | 0.0760 (9) | |
H17A | 0.7412 | −0.0974 | 0.4842 | 0.114* | |
H17B | 0.8273 | 0.0003 | 0.5203 | 0.114* | |
H17C | 0.6398 | 0.0204 | 0.4761 | 0.114* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0646 (4) | 0.0410 (3) | 0.0800 (5) | −0.0074 (3) | −0.0032 (4) | −0.0008 (3) |
N1 | 0.0351 (11) | 0.0367 (10) | 0.0564 (13) | 0.0030 (9) | 0.0010 (10) | −0.0057 (10) |
O1 | 0.0510 (11) | 0.0573 (11) | 0.0599 (11) | −0.0117 (10) | −0.0002 (10) | −0.0092 (10) |
C1 | 0.0438 (15) | 0.0449 (14) | 0.0465 (14) | 0.0021 (12) | −0.0102 (12) | −0.0016 (12) |
C2 | 0.0549 (16) | 0.0486 (15) | 0.0468 (14) | 0.0093 (14) | −0.0023 (14) | −0.0017 (12) |
C3 | 0.082 (2) | 0.0441 (15) | 0.0637 (18) | 0.0150 (16) | −0.0036 (19) | 0.0003 (13) |
C4 | 0.075 (2) | 0.0465 (16) | 0.0612 (18) | −0.0002 (16) | −0.0067 (18) | 0.0110 (14) |
C5 | 0.0526 (17) | 0.0613 (18) | 0.0518 (15) | 0.0011 (14) | 0.0019 (14) | 0.0116 (14) |
C6 | 0.0418 (14) | 0.0481 (15) | 0.0412 (14) | 0.0058 (12) | −0.0045 (12) | −0.0005 (12) |
C7 | 0.0480 (16) | 0.0648 (18) | 0.0548 (16) | 0.0143 (14) | −0.0064 (14) | −0.0095 (14) |
C8 | 0.0487 (14) | 0.0427 (13) | 0.0580 (15) | −0.0064 (12) | 0.0038 (16) | −0.0068 (12) |
C9 | 0.069 (2) | 0.079 (2) | 0.0548 (17) | −0.0063 (16) | −0.0068 (16) | −0.0108 (15) |
C10 | 0.097 (3) | 0.098 (3) | 0.0581 (19) | 0.006 (2) | 0.011 (2) | 0.0047 (19) |
C11 | 0.064 (2) | 0.081 (2) | 0.090 (2) | 0.0074 (19) | 0.0260 (18) | 0.032 (2) |
C12 | 0.0355 (14) | 0.0537 (15) | 0.089 (2) | −0.0017 (13) | 0.0097 (17) | 0.0049 (15) |
C13 | 0.116 (3) | 0.0552 (18) | 0.112 (3) | −0.0128 (19) | 0.006 (2) | 0.0209 (19) |
C14 | 0.0469 (15) | 0.0580 (16) | 0.0477 (15) | 0.0053 (14) | −0.0022 (13) | −0.0067 (13) |
C15 | 0.0618 (19) | 0.0656 (19) | 0.0687 (19) | 0.0218 (15) | −0.0073 (15) | −0.0084 (15) |
C16 | 0.0648 (18) | 0.0756 (18) | 0.0588 (17) | 0.0082 (19) | −0.0110 (16) | −0.0234 (16) |
C17 | 0.069 (2) | 0.086 (2) | 0.073 (2) | 0.013 (2) | 0.0170 (19) | −0.0082 (17) |
Geometric parameters (Å, º) top
N1—C8 | 1.493 (3) | C9—H9B | 0.97 |
N1—C12 | 1.493 (3) | C10—C11 | 1.502 (5) |
N1—C7 | 1.507 (3) | C10—H10A | 0.97 |
N1—H1 | 0.91 | C10—H10B | 0.97 |
O1—C1 | 1.387 (3) | C11—C12 | 1.523 (4) |
O1—H1A | 0.82 | C11—H11A | 0.97 |
C1—C2 | 1.391 (3) | C11—H11B | 0.97 |
C1—C6 | 1.395 (3) | C12—H12A | 0.97 |
C2—C3 | 1.386 (4) | C12—H12B | 0.97 |
C2—C7 | 1.501 (4) | C13—H13A | 0.96 |
C3—C4 | 1.378 (4) | C13—H13B | 0.96 |
C3—H3 | 0.93 | C13—H13C | 0.96 |
C4—C5 | 1.386 (4) | C14—C17 | 1.518 (4) |
C4—C13 | 1.507 (4) | C14—C15 | 1.536 (4) |
C5—C6 | 1.384 (4) | C14—C16 | 1.538 (4) |
C5—H5 | 0.93 | C15—H15A | 0.96 |
C6—C14 | 1.546 (4) | C15—H15B | 0.96 |
C7—H7A | 0.97 | C15—H15C | 0.96 |
C7—H7B | 0.97 | C16—H16A | 0.96 |
C8—C9 | 1.502 (4) | C16—H16B | 0.96 |
C8—H8A | 0.97 | C16—H16C | 0.96 |
C8—H8B | 0.97 | C17—H17A | 0.96 |
C9—C10 | 1.506 (5) | C17—H17B | 0.96 |
C9—H9A | 0.97 | C17—H17C | 0.96 |
| | | |
C8—N1—C12 | 110.98 (19) | C11—C10—H10B | 109.8 |
C8—N1—C7 | 111.88 (19) | C9—C10—H10B | 109.8 |
C12—N1—C7 | 110.1 (2) | H10A—C10—H10B | 108.3 |
C8—N1—H1 | 107.9 | C10—C11—C12 | 111.8 (3) |
C12—N1—H1 | 107.9 | C10—C11—H11A | 109.3 |
C7—N1—H1 | 107.9 | C12—C11—H11A | 109.3 |
C1—O1—H1A | 109.5 | C10—C11—H11B | 109.3 |
O1—C1—C2 | 117.6 (2) | C12—C11—H11B | 109.3 |
O1—C1—C6 | 120.6 (2) | H11A—C11—H11B | 107.9 |
C2—C1—C6 | 121.8 (2) | N1—C12—C11 | 110.5 (2) |
C3—C2—C1 | 118.7 (3) | N1—C12—H12A | 109.6 |
C3—C2—C7 | 121.3 (2) | C11—C12—H12A | 109.6 |
C1—C2—C7 | 120.0 (2) | N1—C12—H12B | 109.6 |
C4—C3—C2 | 121.6 (3) | C11—C12—H12B | 109.6 |
C4—C3—H3 | 119.2 | H12A—C12—H12B | 108.1 |
C2—C3—H3 | 119.2 | C4—C13—H13A | 109.5 |
C3—C4—C5 | 117.5 (3) | C4—C13—H13B | 109.5 |
C3—C4—C13 | 121.5 (3) | H13A—C13—H13B | 109.5 |
C5—C4—C13 | 121.0 (3) | C4—C13—H13C | 109.5 |
C6—C5—C4 | 123.8 (3) | H13A—C13—H13C | 109.5 |
C6—C5—H5 | 118.1 | H13B—C13—H13C | 109.5 |
C4—C5—H5 | 118.1 | C17—C14—C15 | 108.1 (2) |
C5—C6—C1 | 116.4 (2) | C17—C14—C16 | 107.8 (2) |
C5—C6—C14 | 121.4 (2) | C15—C14—C16 | 109.7 (2) |
C1—C6—C14 | 122.2 (2) | C17—C14—C6 | 111.6 (2) |
C2—C7—N1 | 113.6 (2) | C15—C14—C6 | 109.0 (2) |
C2—C7—H7A | 108.8 | C16—C14—C6 | 110.5 (2) |
N1—C7—H7A | 108.8 | C14—C15—H15A | 109.5 |
C2—C7—H7B | 108.8 | C14—C15—H15B | 109.5 |
N1—C7—H7B | 108.8 | H15A—C15—H15B | 109.5 |
H7A—C7—H7B | 107.7 | C14—C15—H15C | 109.5 |
N1—C8—C9 | 110.7 (2) | H15A—C15—H15C | 109.5 |
N1—C8—H8A | 109.5 | H15B—C15—H15C | 109.5 |
C9—C8—H8A | 109.5 | C14—C16—H16A | 109.5 |
N1—C8—H8B | 109.5 | C14—C16—H16B | 109.5 |
C9—C8—H8B | 109.5 | H16A—C16—H16B | 109.5 |
H8A—C8—H8B | 108.1 | C14—C16—H16C | 109.5 |
C8—C9—C10 | 111.2 (3) | H16A—C16—H16C | 109.5 |
C8—C9—H9A | 109.4 | H16B—C16—H16C | 109.5 |
C10—C9—H9A | 109.4 | C14—C17—H17A | 109.5 |
C8—C9—H9B | 109.4 | C14—C17—H17B | 109.5 |
C10—C9—H9B | 109.4 | H17A—C17—H17B | 109.5 |
H9A—C9—H9B | 108.0 | C14—C17—H17C | 109.5 |
C11—C10—C9 | 109.3 (3) | H17A—C17—H17C | 109.5 |
C11—C10—H10A | 109.8 | H17B—C17—H17C | 109.5 |
C9—C10—H10A | 109.8 | | |
| | | |
O1—C1—C2—C3 | 179.1 (2) | C1—C2—C7—N1 | 84.0 (3) |
C6—C1—C2—C3 | −3.4 (4) | C8—N1—C7—C2 | 66.1 (3) |
O1—C1—C2—C7 | −3.2 (3) | C12—N1—C7—C2 | −170.0 (2) |
C6—C1—C2—C7 | 174.3 (2) | C12—N1—C8—C9 | 57.3 (3) |
C1—C2—C3—C4 | 0.0 (4) | C7—N1—C8—C9 | −179.2 (2) |
C7—C2—C3—C4 | −177.7 (3) | N1—C8—C9—C10 | −58.3 (3) |
C2—C3—C4—C5 | 3.2 (4) | C8—C9—C10—C11 | 57.1 (4) |
C2—C3—C4—C13 | −176.5 (3) | C9—C10—C11—C12 | −56.0 (4) |
C3—C4—C5—C6 | −3.4 (4) | C8—N1—C12—C11 | −55.7 (3) |
C13—C4—C5—C6 | 176.3 (3) | C7—N1—C12—C11 | 179.8 (2) |
C4—C5—C6—C1 | 0.3 (4) | C10—C11—C12—N1 | 55.9 (3) |
C4—C5—C6—C14 | −179.4 (3) | C5—C6—C14—C17 | −3.7 (3) |
O1—C1—C6—C5 | −179.3 (2) | C1—C6—C14—C17 | 176.7 (2) |
C2—C1—C6—C5 | 3.2 (3) | C5—C6—C14—C15 | 115.8 (3) |
O1—C1—C6—C14 | 0.3 (3) | C1—C6—C14—C15 | −63.9 (3) |
C2—C1—C6—C14 | −177.2 (2) | C5—C6—C14—C16 | −123.6 (3) |
C3—C2—C7—N1 | −98.4 (3) | C1—C6—C14—C16 | 56.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl1i | 0.91 | 2.23 | 3.137 (3) | 173 |
O1—H1A···Cl1i | 0.82 | 2.23 | 3.047 (3) | 174 |
C12—H12B···Cl1ii | 0.97 | 2.91 | 3.799 (4) | 153 |
C15—H15C···O1iii | 0.96 | 2.56 | 3.487 (3) | 162 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x−1, y, z; (iii) x+1, y, z. |