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Mol­ecules of the title compound, C23H22N2O, have normal geometric parameters. An intra­molecular O—H...N hydrogen bond stabilizes the mol­ecular conformation. The crystal packing is characterized by helical chains of mol­ecules linked by C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703259X/bt2428sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680703259X/bt2428Isup2.hkl
Contains datablock I

CCDC reference: 657712

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.050
  • wR factor = 0.100
  • Data-to-parameter ratio = 15.7

checkCIF/PLATON results

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Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C11 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 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 0 ALERT type 5 Informative message, check

Comment top

Betti-type reaction is an important method to synthesize chiral ligands and by this method many unnatural homochiral amino-phenol compounds have been obtained (Lu et al., 2002; Xu et al., 2004; Wang et al., 2005).

Molecules of the title compound have normal geometric parameters. An intramolecular O—H···N hydrogen bond stabilizes the molecule conformation. The crystal packing is characterized by helical chains of molecules linked by C—H···O hydrogen bonds.

Related literature top

For unnatural homochiral aminophenol compounds obtained by Betti-type reaction, see: Lu et al. (2002); Xu et al. (2004); Wang et al. (2005).

Experimental top

2-naphthol (40 mmol, 5.77 g), 3-formylbenzonitrile (40 mmol, 5.25 g) and piperidine (40 mmol, 3.4 g) were added in a flask and reacted at 80 °C with stirring for one day. Then 50 ml e thanol was added to the flask and all the reactants were refluxed for five hours. After cooled to room temperature, the solution was filtered and white solid (compound I) was obtained as colorless block crystal.

Refinement top

H atoms bonded to O atoms were located in a difference map and refined with distance restraints of O—H = 0.84 (2) Å, and with Uiso(H) = 1.2Ueq(O). Other H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.97 Å and with Uiso(H) = 1.2 times Ueq(C).

Structure description top

Betti-type reaction is an important method to synthesize chiral ligands and by this method many unnatural homochiral amino-phenol compounds have been obtained (Lu et al., 2002; Xu et al., 2004; Wang et al., 2005).

Molecules of the title compound have normal geometric parameters. An intramolecular O—H···N hydrogen bond stabilizes the molecule conformation. The crystal packing is characterized by helical chains of molecules linked by C—H···O hydrogen bonds.

For unnatural homochiral aminophenol compounds obtained by Betti-type reaction, see: Lu et al. (2002); Xu et al. (2004); Wang et al. (2005).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. Packing diagram of the title compound. H atoms except H1A, H15 and H11 have been omitted for clarity.
3-[(2-Hydroxy-1-naphthyl)(piperidin-1-yl)methyl]benzonitrile top
Crystal data top
C23H22N2OF(000) = 728
Mr = 342.43Dx = 1.199 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1875 reflections
a = 11.9008 (13) Åθ = 2.2–21.5°
b = 15.0138 (17) ŵ = 0.07 mm1
c = 10.8886 (13) ÅT = 291 K
β = 102.867 (3)°Block, colourless
V = 1896.7 (4) Å30.30 × 0.26 × 0.24 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
3731 independent reflections
Radiation source: sealed tube2420 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
φ and ω scansθmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1414
Tmin = 0.98, Tmax = 0.98k = 1418
11353 measured reflectionsl = 1313
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.04P)2]
where P = (Fo2 + 2Fc2)/3
3731 reflections(Δ/σ)max < 0.001
238 parametersΔρmax = 0.11 e Å3
0 restraintsΔρmin = 0.11 e Å3
Crystal data top
C23H22N2OV = 1896.7 (4) Å3
Mr = 342.43Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.9008 (13) ŵ = 0.07 mm1
b = 15.0138 (17) ÅT = 291 K
c = 10.8886 (13) Å0.30 × 0.26 × 0.24 mm
β = 102.867 (3)°
Data collection top
Bruker SMART APEX CCD
diffractometer
3731 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
2420 reflections with I > 2σ(I)
Tmin = 0.98, Tmax = 0.98Rint = 0.037
11353 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.11 e Å3
3731 reflectionsΔρmin = 0.11 e Å3
238 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. 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
C10.30955 (12)0.12699 (11)0.28437 (15)0.0403 (4)
C20.27607 (14)0.05048 (11)0.21554 (17)0.0485 (4)
C30.32243 (16)0.02771 (12)0.11143 (18)0.0553 (5)
H30.29520.02200.06290.066*
C40.40741 (16)0.07881 (12)0.08203 (18)0.0566 (5)
H40.44030.06150.01590.068*
C50.44673 (14)0.15727 (12)0.14922 (18)0.0497 (4)
C60.53715 (14)0.20855 (12)0.12228 (18)0.0518 (5)
H60.57360.18970.05970.062*
C70.57231 (16)0.28492 (13)0.18571 (19)0.0615 (5)
H70.63290.31780.16790.074*
C80.51596 (15)0.31318 (13)0.27803 (18)0.0591 (5)
H80.53830.36650.31990.071*
C90.42956 (15)0.26544 (13)0.30865 (17)0.0555 (5)
H90.39320.28690.37000.067*
C100.39372 (13)0.18291 (11)0.24820 (16)0.0436 (4)
C110.25970 (13)0.15140 (10)0.39746 (16)0.0433 (4)
H110.31760.18610.45640.052*
C120.15260 (14)0.20908 (11)0.35548 (17)0.0460 (4)
C130.06387 (15)0.18524 (12)0.25509 (19)0.0553 (5)
H130.06980.13300.21100.066*
C140.03407 (14)0.23828 (11)0.21927 (17)0.0500 (4)
C150.04187 (17)0.31443 (13)0.28523 (19)0.0644 (5)
H150.10750.34960.26240.077*
C160.04448 (15)0.34030 (13)0.38410 (19)0.0597 (5)
H160.03830.39300.42700.072*
C170.14176 (16)0.28668 (11)0.41951 (18)0.0569 (5)
H170.20030.30350.48730.068*
C180.12332 (15)0.21210 (11)0.11744 (19)0.0490 (4)
C190.17039 (16)0.08659 (13)0.56160 (19)0.0585 (5)
H19A0.09810.11570.52430.070*
H19B0.21480.12640.62420.070*
C200.14652 (16)0.00002 (13)0.6246 (2)0.0622 (5)
H20A0.10560.01340.69010.075*
H20B0.09740.03770.56270.075*
C210.25598 (17)0.04955 (14)0.68138 (19)0.0649 (5)
H21A0.23750.10630.71450.078*
H21B0.30180.01530.75020.078*
C220.32365 (16)0.06450 (13)0.58052 (19)0.0613 (5)
H22B0.28100.10420.51660.074*
H22A0.39680.09250.61770.074*
C230.34519 (14)0.02330 (13)0.52003 (19)0.0553 (5)
H23A0.39160.06180.58310.066*
H23B0.38760.01230.45510.066*
N10.23443 (10)0.06843 (9)0.46359 (14)0.0472 (4)
N20.19638 (14)0.19212 (12)0.03453 (17)0.0689 (5)
O10.19695 (11)0.00654 (8)0.24320 (13)0.0568 (3)
H1A0.1741 (17)0.0125 (14)0.306 (2)0.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0355 (7)0.0412 (9)0.0427 (9)0.0043 (6)0.0054 (7)0.0003 (7)
C20.0498 (9)0.0394 (9)0.0551 (11)0.0039 (8)0.0093 (8)0.0010 (8)
C30.0623 (11)0.0405 (9)0.0615 (12)0.0136 (8)0.0106 (9)0.0089 (8)
C40.0647 (11)0.0565 (11)0.0510 (11)0.0148 (10)0.0181 (9)0.0013 (9)
C50.0453 (9)0.0527 (10)0.0539 (11)0.0040 (8)0.0173 (8)0.0041 (8)
C60.0464 (9)0.0604 (12)0.0532 (11)0.0159 (9)0.0206 (8)0.0172 (9)
C70.0581 (11)0.0619 (13)0.0633 (13)0.0099 (9)0.0109 (10)0.0198 (10)
C80.0597 (11)0.0615 (12)0.0533 (12)0.0201 (9)0.0067 (9)0.0022 (9)
C90.0548 (10)0.0633 (12)0.0479 (11)0.0189 (9)0.0102 (8)0.0013 (9)
C100.0369 (8)0.0509 (10)0.0411 (9)0.0058 (7)0.0046 (7)0.0070 (7)
C110.0395 (8)0.0406 (8)0.0499 (10)0.0042 (7)0.0098 (7)0.0003 (7)
C120.0416 (8)0.0450 (9)0.0558 (11)0.0043 (7)0.0201 (8)0.0129 (8)
C130.0588 (10)0.0454 (10)0.0653 (12)0.0003 (9)0.0217 (9)0.0090 (9)
C140.0503 (10)0.0417 (9)0.0596 (11)0.0122 (8)0.0158 (8)0.0164 (8)
C150.0689 (12)0.0550 (12)0.0592 (12)0.0147 (10)0.0073 (10)0.0098 (9)
C160.0621 (11)0.0542 (11)0.0633 (13)0.0126 (9)0.0147 (10)0.0117 (9)
C170.0643 (11)0.0423 (10)0.0533 (11)0.0030 (8)0.0101 (9)0.0094 (8)
C180.0500 (10)0.0491 (10)0.0548 (11)0.0025 (8)0.0264 (9)0.0040 (8)
C190.0560 (10)0.0628 (12)0.0614 (12)0.0023 (9)0.0234 (9)0.0091 (10)
C200.0606 (11)0.0656 (12)0.0610 (12)0.0086 (10)0.0149 (9)0.0154 (10)
C210.0696 (12)0.0693 (13)0.0577 (12)0.0199 (10)0.0183 (10)0.0159 (10)
C220.0634 (11)0.0590 (11)0.0647 (13)0.0303 (10)0.0213 (10)0.0200 (10)
C230.0429 (9)0.0651 (12)0.0584 (12)0.0137 (9)0.0120 (8)0.0145 (9)
N10.0390 (7)0.0481 (8)0.0547 (9)0.0042 (6)0.0110 (6)0.0129 (7)
N20.0621 (10)0.0778 (12)0.0612 (11)0.0263 (9)0.0021 (9)0.0027 (9)
O10.0627 (8)0.0454 (7)0.0613 (9)0.0108 (6)0.0118 (6)0.0089 (6)
Geometric parameters (Å, º) top
C1—C21.381 (2)C14—C151.364 (3)
C1—C101.428 (2)C14—C181.410 (3)
C1—C111.526 (2)C15—C161.369 (3)
C2—O11.355 (2)C15—H150.9300
C2—C31.409 (3)C16—C171.392 (2)
C3—C41.363 (3)C16—H160.9300
C3—H30.9300C17—H170.9300
C4—C51.410 (3)C18—N21.145 (2)
C4—H40.9300C19—N11.468 (2)
C5—C61.406 (2)C19—C201.525 (3)
C5—C101.418 (2)C19—H19A0.9700
C6—C71.356 (3)C19—H19B0.9700
C6—H60.9300C20—C211.508 (2)
C7—C81.393 (3)C20—H20A0.9700
C7—H70.9300C20—H20B0.9700
C8—C91.355 (2)C21—C221.516 (3)
C8—H80.9300C21—H21A0.9700
C9—C101.423 (2)C21—H21B0.9700
C9—H90.9300C22—C231.521 (3)
C11—N11.502 (2)C22—H22B0.9700
C11—C121.524 (2)C22—H22A0.9700
C11—H110.9800C23—N11.488 (2)
C12—C171.378 (2)C23—H23A0.9700
C12—C131.387 (2)C23—H23B0.9700
C13—C141.394 (2)O1—H1A0.84 (2)
C13—H130.9300
C2—C1—C10118.34 (15)C14—C15—C16121.65 (17)
C2—C1—C11121.38 (15)C14—C15—H15119.2
C10—C1—C11120.27 (14)C16—C15—H15119.2
O1—C2—C1122.39 (16)C15—C16—C17119.09 (17)
O1—C2—C3116.20 (15)C15—C16—H16120.5
C1—C2—C3121.41 (16)C17—C16—H16120.5
C4—C3—C2119.76 (17)C12—C17—C16120.96 (17)
C4—C3—H3120.1C12—C17—H17119.5
C2—C3—H3120.1C16—C17—H17119.5
C3—C4—C5121.74 (18)N2—C18—C14179.0 (2)
C3—C4—H4119.1N1—C19—C20110.32 (16)
C5—C4—H4119.1N1—C19—H19A109.6
C6—C5—C4122.00 (18)C20—C19—H19A109.6
C6—C5—C10120.04 (17)N1—C19—H19B109.6
C4—C5—C10117.95 (16)C20—C19—H19B109.6
C7—C6—C5121.36 (18)H19A—C19—H19B108.1
C7—C6—H6119.3C21—C20—C19111.99 (16)
C5—C6—H6119.3C21—C20—H20A109.2
C6—C7—C8118.79 (17)C19—C20—H20A109.2
C6—C7—H7120.6C21—C20—H20B109.2
C8—C7—H7120.6C19—C20—H20B109.2
C9—C8—C7122.02 (19)H20A—C20—H20B107.9
C9—C8—H8119.0C20—C21—C22109.00 (16)
C7—C8—H8119.0C20—C21—H21A109.9
C8—C9—C10120.84 (18)C22—C21—H21A109.9
C8—C9—H9119.6C20—C21—H21B109.9
C10—C9—H9119.6C22—C21—H21B109.9
C5—C10—C9116.72 (15)H21A—C21—H21B108.3
C5—C10—C1120.54 (16)C21—C22—C23110.69 (16)
C9—C10—C1122.73 (15)C21—C22—H22B109.5
N1—C11—C12111.81 (12)C23—C22—H22B109.5
N1—C11—C1110.06 (13)C21—C22—H22A109.5
C12—C11—C1110.11 (13)C23—C22—H22A109.5
N1—C11—H11108.3H22B—C22—H22A108.1
C12—C11—H11108.3N1—C23—C22110.76 (14)
C1—C11—H11108.3N1—C23—H23A109.5
C17—C12—C13118.43 (15)C22—C23—H23A109.5
C17—C12—C11119.65 (16)N1—C23—H23B109.5
C13—C12—C11121.91 (15)C22—C23—H23B109.5
C12—C13—C14121.04 (16)H23A—C23—H23B108.1
C12—C13—H13119.5C19—N1—C23109.87 (14)
C14—C13—H13119.5C19—N1—C11112.71 (13)
C15—C14—C13118.83 (17)C23—N1—C11108.79 (12)
C15—C14—C18121.33 (16)C2—O1—H1A109.5 (14)
C13—C14—C18119.83 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.84 (2)1.90 (2)2.598 (2)139.3 (19)
C15—H15···O1i0.932.403.236 (2)149
Symmetry code: (i) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC23H22N2O
Mr342.43
Crystal system, space groupMonoclinic, P21/c
Temperature (K)291
a, b, c (Å)11.9008 (13), 15.0138 (17), 10.8886 (13)
β (°) 102.867 (3)
V3)1896.7 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.30 × 0.26 × 0.24
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.98, 0.98
No. of measured, independent and
observed [I > 2σ(I)] reflections
11353, 3731, 2420
Rint0.037
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.100, 1.02
No. of reflections3731
No. of parameters238
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.11, 0.11

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXTL (Bruker, 2000), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.84 (2)1.90 (2)2.598 (2)139.3 (19)
C15—H15···O1i0.932.403.236 (2)149
Symmetry code: (i) x, y+1/2, z+1/2.
 

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