Literature DB >> 23125728

1-[(2-Methyl-piperidin-1-yl)(phen-yl)meth-yl]naphthalen-2-ol.

Yao Huang1.   

Abstract

In the title compound, C(23)H(25)NO, an intra-molecular O-H⋯N hydrogen bond defines the mol-ecular conformation; the naphthol mean plane and the benzene ring form a dihedral angle of 75.8 (2)°. The piperidine ring adopts a chair conformation. The crystal packing exhibits no short inter-molecular contacts.

Entities:  

Year:  2012        PMID： 23125728      PMCID： PMC3470315          DOI： 10.1107/S1600536812038652

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the crystal structures of related compounds, see: Wang & Zhao (2009 ▶); Lu et al. (2002 ▶). For background to Betti-type reactions, see: Pu & Yu (2001 ▶).

Experimental

Crystal data

C23H25NO M = 331.44 Orthorhombic, a = 10.249 (2) Å b = 13.182 (3) Å c = 13.435 (3) Å V = 1815.1 (6) Å3 Z = 4 Mo Kα radiation μ = 0.07 mm−1 T = 293 K 0.34 × 0.32 × 0.26 mm

Data collection

Rigaku SCXmini diffractometer Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.097, T max = 0.099 18098 measured reflections 2170 independent reflections 1718 reflections with I > 2σ(I) R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.054 wR(F 2) = 0.162 S = 1.13 2170 reflections 228 parameters 1 restraint H-atom parameters constrained Δρmax = 0.32 e Å−3 Δρmin = −0.20 e Å−3 Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812038652/cv5314sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038652/cv5314Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812038652/cv5314Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C23H25NOF(000) = 712
Mr = 331.44Dx = 1.213 Mg m−3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 2170 reflections
a = 10.249 (2) Åθ = 2.2–27.5°
b = 13.182 (3) ŵ = 0.07 mm−1
c = 13.435 (3) ÅT = 293 K
V = 1815.1 (6) Å3Block, pale yellow
Z = 40.34 × 0.32 × 0.26 mm
Rigaku SCXmini diffractometer2170 independent reflections
Radiation source: fine-focus sealed tube1718 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 2.2°
CCD_Profile_fitting scansh = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −17→17
Tmin = 0.097, Tmax = 0.099l = −17→17
18098 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H-atom parameters constrained
S = 1.13w = 1/[σ2(Fo2) + (0.0945P)2 + 0.0807P] where P = (Fo2 + 2Fc2)/3
2170 reflections(Δ/σ)max < 0.001
228 parametersΔρmax = 0.32 e Å−3
1 restraintΔρmin = −0.20 e Å−3
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.
xyzUiso*/Ueq
C10.6335 (3)0.5998 (2)0.4126 (3)0.0416 (7)
H10.59350.63380.46980.050*
C20.7644 (3)0.5578 (2)0.4460 (2)0.0385 (7)
C30.8185 (3)0.4734 (2)0.4004 (2)0.0419 (7)
C40.9413 (4)0.4362 (3)0.4301 (3)0.0506 (9)
H40.97700.38050.39750.061*
C51.0082 (4)0.4805 (3)0.5052 (3)0.0530 (9)
H51.08860.45410.52430.064*
C60.9578 (3)0.5657 (3)0.5550 (2)0.0432 (8)
C70.8359 (3)0.6068 (2)0.5242 (2)0.0377 (7)
C80.7907 (4)0.6945 (3)0.5741 (3)0.0471 (8)
H80.71210.72390.55490.057*
C90.8611 (4)0.7370 (3)0.6504 (3)0.0570 (10)
H90.82930.79450.68240.068*
C100.9793 (4)0.6952 (3)0.6805 (3)0.0597 (10)
H101.02600.72460.73240.072*
C111.0262 (4)0.6118 (3)0.6343 (3)0.0564 (10)
H111.10510.58420.65520.068*
C120.6500 (3)0.6787 (2)0.3296 (3)0.0440 (8)
C130.5835 (4)0.7694 (3)0.3331 (4)0.0680 (12)
H130.52750.78240.38600.082*
C140.5983 (5)0.8419 (3)0.2589 (5)0.0799 (14)
H140.55130.90220.26200.096*
C150.6808 (5)0.8253 (3)0.1821 (4)0.0728 (13)
H150.69120.87440.13300.087*
C160.7491 (5)0.7361 (4)0.1767 (4)0.0680 (12)
H160.80500.72420.12350.082*
C170.7347 (4)0.6639 (3)0.2505 (3)0.0535 (9)
H170.78280.60420.24700.064*
C180.4314 (4)0.5414 (3)0.3252 (4)0.0650 (12)
H18A0.45710.58310.26910.078*
H18B0.37180.58030.36620.078*
C190.3633 (5)0.4449 (3)0.2877 (5)0.0781 (15)
H19A0.28380.46350.25310.094*
H19B0.41990.41050.24070.094*
C200.3305 (5)0.3737 (4)0.3718 (4)0.0833 (16)
H20A0.26290.40350.41300.100*
H20B0.29740.31050.34490.100*
C210.4491 (5)0.3531 (4)0.4338 (4)0.0765 (14)
H21A0.51180.31520.39450.092*
H21B0.42460.31150.49040.092*
C220.5127 (5)0.4498 (4)0.4711 (3)0.0703 (13)
H220.59410.43120.50470.084*
C230.4262 (8)0.5059 (6)0.5467 (5)0.120 (3)
H23A0.34990.53150.51370.180*
H23B0.47410.56130.57520.180*
H23C0.40050.45980.59850.180*
N10.5467 (3)0.5133 (2)0.3834 (2)0.0442 (7)
O10.7570 (3)0.4224 (2)0.3269 (2)0.0563 (7)
H1A0.67930.43730.32700.084*
U11U22U33U12U13U23
C10.0343 (16)0.0435 (17)0.0469 (18)−0.0004 (12)0.0041 (13)−0.0160 (14)
C20.0350 (16)0.0405 (16)0.0401 (17)−0.0022 (12)0.0054 (13)−0.0026 (13)
C30.0427 (17)0.0414 (16)0.0415 (18)0.0026 (13)0.0056 (14)−0.0064 (14)
C40.049 (2)0.0487 (19)0.054 (2)0.0105 (15)0.0051 (16)−0.0041 (16)
C50.0392 (18)0.061 (2)0.059 (2)0.0085 (16)0.0010 (16)0.0044 (18)
C60.0407 (17)0.0453 (18)0.0435 (18)−0.0080 (13)0.0016 (14)0.0085 (13)
C70.0391 (16)0.0371 (14)0.0368 (15)−0.0072 (12)0.0023 (13)0.0022 (12)
C80.048 (2)0.0457 (19)0.0472 (19)−0.0036 (14)0.0029 (16)−0.0080 (15)
C90.072 (3)0.0490 (19)0.050 (2)−0.0160 (18)0.0031 (19)−0.0113 (17)
C100.073 (3)0.059 (2)0.047 (2)−0.0227 (19)−0.019 (2)−0.0014 (18)
C110.054 (2)0.063 (2)0.052 (2)−0.0093 (18)−0.0151 (18)0.0111 (18)
C120.0361 (17)0.0417 (16)0.0543 (19)−0.0002 (12)−0.0070 (15)−0.0090 (15)
C130.053 (2)0.055 (2)0.095 (3)0.0091 (18)0.003 (2)−0.003 (2)
C140.067 (3)0.049 (2)0.123 (4)0.009 (2)−0.012 (3)0.015 (3)
C150.071 (3)0.063 (3)0.085 (3)−0.009 (2)−0.029 (3)0.020 (2)
C160.079 (3)0.072 (3)0.053 (2)−0.002 (2)−0.002 (2)0.008 (2)
C170.062 (2)0.049 (2)0.049 (2)0.0051 (16)−0.0020 (17)−0.0045 (16)
C180.040 (2)0.056 (2)0.099 (3)0.0055 (16)−0.021 (2)−0.028 (2)
C190.054 (3)0.066 (3)0.114 (4)−0.004 (2)−0.023 (3)−0.030 (3)
C200.060 (3)0.077 (3)0.114 (4)−0.027 (2)0.029 (3)−0.038 (3)
C210.082 (3)0.071 (3)0.076 (3)−0.031 (2)0.021 (3)−0.013 (2)
C220.080 (3)0.073 (3)0.057 (2)−0.034 (2)0.014 (2)−0.007 (2)
C230.135 (6)0.143 (6)0.082 (4)−0.052 (5)0.034 (4)−0.037 (4)
N10.0385 (14)0.0450 (15)0.0491 (16)−0.0056 (11)0.0005 (12)−0.0121 (12)
O10.0545 (16)0.0564 (15)0.0581 (16)0.0022 (11)−0.0002 (13)−0.0246 (13)
C1—N11.498 (4)C14—H140.9300
C1—C21.519 (5)C15—C161.370 (7)
C1—C121.534 (5)C15—H150.9300
C1—H10.9800C16—C171.382 (6)
C2—C31.387 (4)C16—H160.9300
C2—C71.434 (5)C17—H170.9300
C3—O11.350 (4)C18—N11.464 (5)
C3—C41.408 (5)C18—C191.535 (5)
C4—C51.353 (6)C18—H18A0.9700
C4—H40.9300C18—H18B0.9700
C5—C61.406 (5)C19—C201.506 (8)
C5—H50.9300C19—H19A0.9700
C6—C111.414 (5)C19—H19B0.9700
C6—C71.422 (5)C20—C211.499 (8)
C7—C81.415 (5)C20—H20A0.9700
C8—C91.373 (5)C20—H20B0.9700
C8—H80.9300C21—C221.517 (6)
C9—C101.392 (6)C21—H21A0.9700
C9—H90.9300C21—H21B0.9700
C10—C111.350 (6)C22—N11.486 (5)
C10—H100.9300C22—C231.538 (8)
C11—H110.9300C22—H220.9800
C12—C131.378 (5)C23—H23A0.9600
C12—C171.387 (5)C23—H23B0.9600
C13—C141.389 (8)C23—H23C0.9600
C13—H130.9300O1—H1A0.8200
C14—C151.351 (8)
N1—C1—C2109.0 (3)C16—C15—H15120.0
N1—C1—C12113.0 (3)C15—C16—C17119.9 (5)
C2—C1—C12111.4 (3)C15—C16—H16120.0
N1—C1—H1107.7C17—C16—H16120.0
C2—C1—H1107.7C16—C17—C12121.3 (4)
C12—C1—H1107.7C16—C17—H17119.3
C3—C2—C7118.7 (3)C12—C17—H17119.3
C3—C2—C1120.9 (3)N1—C18—C19109.4 (3)
C7—C2—C1120.3 (3)N1—C18—H18A109.8
O1—C3—C2122.4 (3)C19—C18—H18A109.8
O1—C3—C4116.8 (3)N1—C18—H18B109.8
C2—C3—C4120.8 (3)C19—C18—H18B109.8
C5—C4—C3121.0 (3)H18A—C18—H18B108.2
C5—C4—H4119.5C20—C19—C18111.8 (4)
C3—C4—H4119.5C20—C19—H19A109.2
C4—C5—C6120.9 (3)C18—C19—H19A109.2
C4—C5—H5119.6C20—C19—H19B109.2
C6—C5—H5119.6C18—C19—H19B109.2
C5—C6—C11121.3 (3)H19A—C19—H19B107.9
C5—C6—C7119.3 (3)C21—C20—C19110.4 (4)
C11—C6—C7119.4 (3)C21—C20—H20A109.6
C8—C7—C6117.5 (3)C19—C20—H20A109.6
C8—C7—C2123.1 (3)C21—C20—H20B109.6
C6—C7—C2119.4 (3)C19—C20—H20B109.6
C9—C8—C7121.0 (4)H20A—C20—H20B108.1
C9—C8—H8119.5C20—C21—C22112.3 (4)
C7—C8—H8119.5C20—C21—H21A109.1
C8—C9—C10120.9 (4)C22—C21—H21A109.1
C8—C9—H9119.6C20—C21—H21B109.1
C10—C9—H9119.6C22—C21—H21B109.1
C11—C10—C9119.9 (4)H21A—C21—H21B107.9
C11—C10—H10120.0N1—C22—C21108.2 (3)
C9—C10—H10120.0N1—C22—C23112.8 (5)
C10—C11—C6121.3 (4)C21—C22—C23112.0 (4)
C10—C11—H11119.3N1—C22—H22107.9
C6—C11—H11119.3C21—C22—H22107.9
C13—C12—C17117.2 (4)C23—C22—H22107.9
C13—C12—C1120.7 (4)C22—C23—H23A109.5
C17—C12—C1122.1 (3)C22—C23—H23B109.5
C12—C13—C14121.3 (5)H23A—C23—H23B109.5
C12—C13—H13119.4C22—C23—H23C109.5
C14—C13—H13119.4H23A—C23—H23C109.5
C15—C14—C13120.3 (4)H23B—C23—H23C109.5
C15—C14—H14119.8C18—N1—C22112.1 (3)
C13—C14—H14119.8C18—N1—C1115.3 (3)
C14—C15—C16119.9 (4)C22—N1—C1111.1 (3)
C14—C15—H15120.0C3—O1—H1A109.5
N1—C1—C2—C336.0 (4)N1—C1—C12—C13102.8 (4)
C12—C1—C2—C3−89.4 (3)C2—C1—C12—C13−134.1 (4)
N1—C1—C2—C7−145.5 (3)N1—C1—C12—C17−79.4 (4)
C12—C1—C2—C789.1 (3)C2—C1—C12—C1743.7 (4)
C7—C2—C3—O1179.4 (3)C17—C12—C13—C141.6 (6)
C1—C2—C3—O1−2.1 (5)C1—C12—C13—C14179.4 (4)
C7—C2—C3—C40.0 (5)C12—C13—C14—C15−1.1 (8)
C1—C2—C3—C4178.5 (3)C13—C14—C15—C160.7 (7)
O1—C3—C4—C5−177.9 (4)C14—C15—C16—C17−0.8 (7)
C2—C3—C4—C51.5 (5)C15—C16—C17—C121.4 (6)
C3—C4—C5—C6−0.9 (6)C13—C12—C17—C16−1.7 (6)
C4—C5—C6—C11179.3 (4)C1—C12—C17—C16−179.5 (4)
C4—C5—C6—C7−1.2 (5)N1—C18—C19—C2055.1 (5)
C5—C6—C7—C8−178.0 (3)C18—C19—C20—C21−52.4 (5)
C11—C6—C7—C81.5 (5)C19—C20—C21—C2254.4 (5)
C5—C6—C7—C22.6 (4)C20—C21—C22—N1−57.5 (5)
C11—C6—C7—C2−177.8 (3)C20—C21—C22—C2367.4 (6)
C3—C2—C7—C8178.7 (3)C19—C18—N1—C22−59.9 (5)
C1—C2—C7—C80.1 (5)C19—C18—N1—C1171.6 (4)
C3—C2—C7—C6−2.0 (4)C21—C22—N1—C1860.9 (5)
C1—C2—C7—C6179.5 (3)C23—C22—N1—C18−63.6 (5)
C6—C7—C8—C9−1.1 (5)C21—C22—N1—C1−168.5 (4)
C2—C7—C8—C9178.2 (3)C23—C22—N1—C167.0 (5)
C7—C8—C9—C100.3 (6)C2—C1—N1—C18−164.4 (3)
C8—C9—C10—C110.1 (6)C12—C1—N1—C18−40.0 (4)
C9—C10—C11—C60.3 (6)C2—C1—N1—C2266.6 (4)
C5—C6—C11—C10178.4 (4)C12—C1—N1—C22−168.9 (3)
C7—C6—C11—C10−1.1 (5)
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.821.852.581 (4)148
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
O1—H1A⋯N10.821.852.581 (4)148
  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

Review 2.  Catalytic asymmetric organozinc additions to carbonyl compounds.

Authors:  L Pu; H B Yu
Journal:  Chem Rev       Date:  2001-03       Impact factor: 60.622

3.  1-[(3-Methyl-piperidin-1-yl)(phen-yl)meth-yl]-2-naphthol.

Authors:  Wen Xiang Wang; Hong Zhao
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-05-14
  3 in total

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