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The title compound, C18H28N2O2, is a product of a Mannich reaction involving hydro­quinone, form­aldehyde and piperidine. The mol­ecule occupies a special position on an inversion centre. The structure is stabilized by an intramolecular O—H...N hydrogen bond linking the phenol OH group and a piperidyl N atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804016344/ya6213sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804016344/ya6213Isup2.hkl
Contains datablock I

CCDC reference: 248780

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.051
  • wR factor = 0.128
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.078 Value of mu given = 0.080
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

2,5-bis(1-piperidinylmethyl)benzene-1,4-diol top
Crystal data top
C18H28N2O2Z = 1
Mr = 304.42F(000) = 166
Triclinic, P1Dx = 1.197 Mg m3
Hall symbol: -P 1Melting point: 469 K
a = 6.372 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.184 (3) ÅCell parameters from 644 reflections
c = 8.649 (3) Åθ = 2.6–25.6°
α = 72.349 (5)°µ = 0.08 mm1
β = 81.745 (6)°T = 293 K
γ = 80.865 (5)°Prism, colourless
V = 422.2 (3) Å30.20 × 0.16 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
982 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
φ and ω scansh = 77
2215 measured reflectionsk = 89
1487 independent reflectionsl = 510
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0504P)2 + 0.1017P]
where P = (Fo2 + 2Fc2)/3
1479 reflections(Δ/σ)max < 0.001
101 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.18 e Å3
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3143 (2)0.1153 (2)0.20974 (19)0.0583 (5)
H10.35280.03380.23020.087*
N10.2925 (3)0.2183 (2)0.2098 (2)0.0450 (5)
C10.1591 (3)0.0548 (3)0.1044 (2)0.0436 (5)
C20.0403 (3)0.1709 (3)0.0821 (2)0.0452 (6)
H20.06890.28720.13830.054*
C30.1196 (3)0.1210 (3)0.0209 (2)0.0422 (5)
C40.2558 (4)0.2465 (3)0.0386 (3)0.0520 (6)
H4A0.39230.23530.02560.062*
H4B0.18680.36320.00400.062*
C50.4543 (4)0.3219 (3)0.2205 (3)0.0565 (7)
H5A0.40560.44350.17460.068*
H5B0.58570.29350.15700.068*
C60.4975 (4)0.2899 (3)0.3947 (3)0.0652 (7)
H6A0.60000.36420.39830.078*
H6B0.55950.17090.43710.078*
C70.2954 (4)0.3242 (4)0.5005 (3)0.0651 (7)
H7A0.24370.44660.46830.078*
H7B0.32480.29140.61360.078*
C80.1266 (4)0.2217 (3)0.4828 (3)0.0553 (6)
H8A0.17050.09930.52900.066*
H8B0.00690.25250.54280.066*
C90.0935 (3)0.2569 (3)0.3067 (2)0.0459 (6)
H9A0.01160.18710.29830.055*
H9B0.03810.37740.26340.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0591 (10)0.0593 (11)0.0607 (11)0.0021 (8)0.0236 (8)0.0203 (8)
N10.0410 (10)0.0542 (12)0.0452 (11)0.0114 (8)0.0009 (8)0.0210 (9)
C10.0440 (12)0.0519 (15)0.0367 (12)0.0024 (10)0.0043 (10)0.0169 (10)
C20.0555 (13)0.0401 (13)0.0385 (13)0.0020 (10)0.0045 (11)0.0110 (10)
C30.0463 (12)0.0486 (14)0.0335 (12)0.0099 (10)0.0022 (10)0.0153 (10)
C40.0574 (14)0.0564 (14)0.0445 (14)0.0163 (11)0.0006 (11)0.0158 (11)
C50.0454 (13)0.0663 (16)0.0656 (17)0.0189 (11)0.0011 (12)0.0273 (13)
C60.0532 (15)0.0772 (18)0.0780 (19)0.0128 (13)0.0160 (13)0.0345 (15)
C70.0686 (17)0.0751 (18)0.0623 (17)0.0038 (13)0.0142 (13)0.0347 (14)
C80.0580 (15)0.0621 (15)0.0476 (14)0.0065 (12)0.0003 (11)0.0214 (12)
C90.0400 (12)0.0511 (13)0.0497 (14)0.0093 (10)0.0000 (10)0.0190 (11)
Geometric parameters (Å, º) top
O1—C11.372 (2)C5—H5A0.9700
O1—H10.8200C5—H5B0.9700
N1—C41.475 (3)C6—C71.509 (3)
N1—C51.464 (3)C6—H6A0.9700
N1—C91.463 (3)C6—H6B0.9700
C1—C21.376 (3)C7—C81.515 (3)
C1—C3i1.401 (3)C7—H7A0.9700
C2—C31.381 (3)C7—H7B0.9700
C2—H20.9300C8—C91.501 (3)
C3—C1i1.401 (3)C8—H8A0.9700
C3—C41.500 (3)C8—H8B0.9700
C4—H4A0.9700C9—H9A0.9700
C4—H4B0.9700C9—H9B0.9700
C5—C61.507 (3)
C1—O1—H1109.5C5—C6—C7111.39 (19)
C9—N1—C5110.46 (16)C5—C6—H6A109.3
C9—N1—C4110.95 (17)C7—C6—H6A109.3
C5—N1—C4110.96 (17)C5—C6—H6B109.3
O1—C1—C2118.6 (2)C7—C6—H6B109.3
O1—C1—C3i121.42 (19)H6A—C6—H6B108.0
C2—C1—C3i119.97 (19)C6—C7—C8109.78 (19)
C1—C2—C3122.4 (2)C6—C7—H7A109.7
C1—C2—H2118.8C8—C7—H7A109.7
C3—C2—H2118.8C6—C7—H7B109.7
C2—C3—C1i117.66 (19)C8—C7—H7B109.7
C2—C3—C4122.2 (2)H7A—C7—H7B108.2
C1i—C3—C4120.10 (19)C9—C8—C7110.86 (19)
N1—C4—C3112.28 (17)C9—C8—H8A109.5
N1—C4—H4A109.1C7—C8—H8A109.5
C3—C4—H4A109.1C9—C8—H8B109.5
N1—C4—H4B109.1C7—C8—H8B109.5
C3—C4—H4B109.1H8A—C8—H8B108.1
H4A—C4—H4B107.9N1—C9—C8111.57 (18)
N1—C5—C6111.31 (19)N1—C9—H9A109.3
N1—C5—H5A109.4C8—C9—H9A109.3
C6—C5—H5A109.4N1—C9—H9B109.3
N1—C5—H5B109.4C8—C9—H9B109.3
C6—C5—H5B109.4H9A—C9—H9B108.0
H5A—C5—H5B108.0
O1—C1—C2—C3179.63 (18)C9—N1—C5—C658.2 (2)
C3i—C1—C2—C30.1 (3)C4—N1—C5—C6178.33 (18)
C1—C2—C3—C1i0.1 (3)N1—C5—C6—C756.3 (3)
C1—C2—C3—C4176.92 (19)C5—C6—C7—C853.5 (3)
C9—N1—C4—C366.5 (2)C6—C7—C8—C953.8 (3)
C5—N1—C4—C3170.28 (18)C5—N1—C9—C858.9 (2)
C2—C3—C4—N1138.2 (2)C4—N1—C9—C8177.62 (18)
C1i—C3—C4—N144.9 (3)C7—C8—C9—N157.1 (2)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.822.002.711 (2)146
Symmetry code: (i) x, y, z.
 

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