Download citation
Download citation
link to html
In the crystal structure of the title compound, C17H28NO+·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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803027314/ci6311sup1.cif
Contains datablocks global, IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803027314/ci6311IVsup2.hkl
Contains datablock IV

CCDC reference: 232140

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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+·ClF(000) = 648
Mr = 297.85Dx = 1.124 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 827 reflections
a = 5.882 (2) Åθ = 3.3–22.8°
b = 12.187 (5) ŵ = 0.21 mm1
c = 24.553 (10) ÅT = 293 K
V = 1760.1 (12) Å3Block, colorless
Z = 40.34 × 0.32 × 0.20 mm
Data collection top
Bruker SMART 1000
diffractometer
2288 reflections with I > 2σ(I)
ω scansRint = 0.033
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
θmax = 25.0°, θmin = 2.4°
Tmin = 0.841, Tmax = 1.000h = 57
7868 measured reflectionsk = 1413
3092 independent reflectionsl = 2914
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) = 0.105Δρmax = 0.17 e Å3
S = 1.02Δρmin = 0.16 e Å3
3092 reflectionsAbsolute structure: Flack (1983); 1275 Friedel pairs
186 parametersAbsolute 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
xyzUiso*/Ueq
Cl10.67538 (12)0.38671 (5)0.76206 (3)0.0619 (2)
N10.0416 (3)0.10464 (15)0.73289 (8)0.0427 (5)
H10.12040.04050.73110.051*
O10.1507 (3)0.04949 (14)0.62543 (7)0.0561 (5)
H1A0.19220.07120.65540.084*
C10.2624 (4)0.0475 (2)0.61293 (10)0.0451 (6)
C20.1876 (5)0.1429 (2)0.63841 (10)0.0501 (6)
C30.2985 (5)0.2407 (2)0.62721 (12)0.0632 (8)
H30.24940.30470.64410.076*
C40.4796 (5)0.2453 (2)0.59167 (12)0.0609 (8)
C50.5403 (5)0.1493 (2)0.56519 (11)0.0552 (7)
H50.65690.15240.53970.066*
C60.4373 (4)0.0489 (2)0.57453 (10)0.0437 (6)
C70.0151 (5)0.1392 (2)0.67555 (11)0.0559 (7)
H7A0.12590.08850.66060.067*
H7B0.08460.21140.67650.067*
C80.1879 (5)0.18707 (18)0.76109 (10)0.0498 (6)
H8A0.10920.25690.76270.060*
H8B0.32730.19740.74060.060*
C90.2442 (5)0.1498 (3)0.81782 (11)0.0677 (9)
H9A0.33740.20490.83560.081*
H9B0.33120.08230.81610.081*
C100.0319 (7)0.1310 (3)0.85084 (13)0.0844 (11)
H10A0.07200.10420.88680.101*
H10B0.05000.19960.85510.101*
C110.1158 (6)0.0486 (3)0.82230 (14)0.0780 (10)
H11A0.25600.03940.84260.094*
H11B0.03850.02170.82140.094*
C120.1715 (4)0.0839 (2)0.76430 (13)0.0592 (7)
H12A0.25940.02700.74650.071*
H12B0.26280.15020.76510.071*
C130.6082 (8)0.3504 (2)0.58199 (16)0.0943 (12)
H13A0.50450.40640.57010.141*
H13B0.72150.33870.55450.141*
H13C0.68040.37310.61520.141*
C140.5142 (5)0.0558 (2)0.54409 (11)0.0509 (7)
C150.6119 (5)0.1378 (2)0.58547 (12)0.0654 (8)
H15A0.65680.20370.56690.098*
H15B0.49830.15490.61220.098*
H15C0.74180.10600.60310.098*
C160.3126 (5)0.1083 (2)0.51392 (11)0.0664 (8)
H16A0.25020.05640.48860.100*
H16B0.19790.12910.53980.100*
H16C0.36380.17210.49460.100*
C170.6975 (6)0.0308 (3)0.50233 (13)0.0760 (9)
H17A0.74120.09740.48420.114*
H17B0.82730.00030.52030.114*
H17C0.63980.02040.47610.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0646 (4)0.0410 (3)0.0800 (5)0.0074 (3)0.0032 (4)0.0008 (3)
N10.0351 (11)0.0367 (10)0.0564 (13)0.0030 (9)0.0010 (10)0.0057 (10)
O10.0510 (11)0.0573 (11)0.0599 (11)0.0117 (10)0.0002 (10)0.0092 (10)
C10.0438 (15)0.0449 (14)0.0465 (14)0.0021 (12)0.0102 (12)0.0016 (12)
C20.0549 (16)0.0486 (15)0.0468 (14)0.0093 (14)0.0023 (14)0.0017 (12)
C30.082 (2)0.0441 (15)0.0637 (18)0.0150 (16)0.0036 (19)0.0003 (13)
C40.075 (2)0.0465 (16)0.0612 (18)0.0002 (16)0.0067 (18)0.0110 (14)
C50.0526 (17)0.0613 (18)0.0518 (15)0.0011 (14)0.0019 (14)0.0116 (14)
C60.0418 (14)0.0481 (15)0.0412 (14)0.0058 (12)0.0045 (12)0.0005 (12)
C70.0480 (16)0.0648 (18)0.0548 (16)0.0143 (14)0.0064 (14)0.0095 (14)
C80.0487 (14)0.0427 (13)0.0580 (15)0.0064 (12)0.0038 (16)0.0068 (12)
C90.069 (2)0.079 (2)0.0548 (17)0.0063 (16)0.0068 (16)0.0108 (15)
C100.097 (3)0.098 (3)0.0581 (19)0.006 (2)0.011 (2)0.0047 (19)
C110.064 (2)0.081 (2)0.090 (2)0.0074 (19)0.0260 (18)0.032 (2)
C120.0355 (14)0.0537 (15)0.089 (2)0.0017 (13)0.0097 (17)0.0049 (15)
C130.116 (3)0.0552 (18)0.112 (3)0.0128 (19)0.006 (2)0.0209 (19)
C140.0469 (15)0.0580 (16)0.0477 (15)0.0053 (14)0.0022 (13)0.0067 (13)
C150.0618 (19)0.0656 (19)0.0687 (19)0.0218 (15)0.0073 (15)0.0084 (15)
C160.0648 (18)0.0756 (18)0.0588 (17)0.0082 (19)0.0110 (16)0.0234 (16)
C170.069 (2)0.086 (2)0.073 (2)0.013 (2)0.0170 (19)0.0082 (17)
Geometric parameters (Å, º) top
N1—C81.493 (3)C9—H9B0.97
N1—C121.493 (3)C10—C111.502 (5)
N1—C71.507 (3)C10—H10A0.97
N1—H10.91C10—H10B0.97
O1—C11.387 (3)C11—C121.523 (4)
O1—H1A0.82C11—H11A0.97
C1—C21.391 (3)C11—H11B0.97
C1—C61.395 (3)C12—H12A0.97
C2—C31.386 (4)C12—H12B0.97
C2—C71.501 (4)C13—H13A0.96
C3—C41.378 (4)C13—H13B0.96
C3—H30.93C13—H13C0.96
C4—C51.386 (4)C14—C171.518 (4)
C4—C131.507 (4)C14—C151.536 (4)
C5—C61.384 (4)C14—C161.538 (4)
C5—H50.93C15—H15A0.96
C6—C141.546 (4)C15—H15B0.96
C7—H7A0.97C15—H15C0.96
C7—H7B0.97C16—H16A0.96
C8—C91.502 (4)C16—H16B0.96
C8—H8A0.97C16—H16C0.96
C8—H8B0.97C17—H17A0.96
C9—C101.506 (5)C17—H17B0.96
C9—H9A0.97C17—H17C0.96
C8—N1—C12110.98 (19)C11—C10—H10B109.8
C8—N1—C7111.88 (19)C9—C10—H10B109.8
C12—N1—C7110.1 (2)H10A—C10—H10B108.3
C8—N1—H1107.9C10—C11—C12111.8 (3)
C12—N1—H1107.9C10—C11—H11A109.3
C7—N1—H1107.9C12—C11—H11A109.3
C1—O1—H1A109.5C10—C11—H11B109.3
O1—C1—C2117.6 (2)C12—C11—H11B109.3
O1—C1—C6120.6 (2)H11A—C11—H11B107.9
C2—C1—C6121.8 (2)N1—C12—C11110.5 (2)
C3—C2—C1118.7 (3)N1—C12—H12A109.6
C3—C2—C7121.3 (2)C11—C12—H12A109.6
C1—C2—C7120.0 (2)N1—C12—H12B109.6
C4—C3—C2121.6 (3)C11—C12—H12B109.6
C4—C3—H3119.2H12A—C12—H12B108.1
C2—C3—H3119.2C4—C13—H13A109.5
C3—C4—C5117.5 (3)C4—C13—H13B109.5
C3—C4—C13121.5 (3)H13A—C13—H13B109.5
C5—C4—C13121.0 (3)C4—C13—H13C109.5
C6—C5—C4123.8 (3)H13A—C13—H13C109.5
C6—C5—H5118.1H13B—C13—H13C109.5
C4—C5—H5118.1C17—C14—C15108.1 (2)
C5—C6—C1116.4 (2)C17—C14—C16107.8 (2)
C5—C6—C14121.4 (2)C15—C14—C16109.7 (2)
C1—C6—C14122.2 (2)C17—C14—C6111.6 (2)
C2—C7—N1113.6 (2)C15—C14—C6109.0 (2)
C2—C7—H7A108.8C16—C14—C6110.5 (2)
N1—C7—H7A108.8C14—C15—H15A109.5
C2—C7—H7B108.8C14—C15—H15B109.5
N1—C7—H7B108.8H15A—C15—H15B109.5
H7A—C7—H7B107.7C14—C15—H15C109.5
N1—C8—C9110.7 (2)H15A—C15—H15C109.5
N1—C8—H8A109.5H15B—C15—H15C109.5
C9—C8—H8A109.5C14—C16—H16A109.5
N1—C8—H8B109.5C14—C16—H16B109.5
C9—C8—H8B109.5H16A—C16—H16B109.5
H8A—C8—H8B108.1C14—C16—H16C109.5
C8—C9—C10111.2 (3)H16A—C16—H16C109.5
C8—C9—H9A109.4H16B—C16—H16C109.5
C10—C9—H9A109.4C14—C17—H17A109.5
C8—C9—H9B109.4C14—C17—H17B109.5
C10—C9—H9B109.4H17A—C17—H17B109.5
H9A—C9—H9B108.0C14—C17—H17C109.5
C11—C10—C9109.3 (3)H17A—C17—H17C109.5
C11—C10—H10A109.8H17B—C17—H17C109.5
C9—C10—H10A109.8
O1—C1—C2—C3179.1 (2)C1—C2—C7—N184.0 (3)
C6—C1—C2—C33.4 (4)C8—N1—C7—C266.1 (3)
O1—C1—C2—C73.2 (3)C12—N1—C7—C2170.0 (2)
C6—C1—C2—C7174.3 (2)C12—N1—C8—C957.3 (3)
C1—C2—C3—C40.0 (4)C7—N1—C8—C9179.2 (2)
C7—C2—C3—C4177.7 (3)N1—C8—C9—C1058.3 (3)
C2—C3—C4—C53.2 (4)C8—C9—C10—C1157.1 (4)
C2—C3—C4—C13176.5 (3)C9—C10—C11—C1256.0 (4)
C3—C4—C5—C63.4 (4)C8—N1—C12—C1155.7 (3)
C13—C4—C5—C6176.3 (3)C7—N1—C12—C11179.8 (2)
C4—C5—C6—C10.3 (4)C10—C11—C12—N155.9 (3)
C4—C5—C6—C14179.4 (3)C5—C6—C14—C173.7 (3)
O1—C1—C6—C5179.3 (2)C1—C6—C14—C17176.7 (2)
C2—C1—C6—C53.2 (3)C5—C6—C14—C15115.8 (3)
O1—C1—C6—C140.3 (3)C1—C6—C14—C1563.9 (3)
C2—C1—C6—C14177.2 (2)C5—C6—C14—C16123.6 (3)
C3—C2—C7—N198.4 (3)C1—C6—C14—C1656.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl1i0.912.233.137 (3)173
O1—H1A···Cl1i0.822.233.047 (3)174
C12—H12B···Cl1ii0.972.913.799 (4)153
C15—H15C···O1iii0.962.563.487 (3)162
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x1, y, z; (iii) x+1, y, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds