4-[(2-Hydr­oxy-1-naphth­yl)(piperidin-1-yl)meth­yl]benzonitrile

Zhang, Y.; Li, Y.H.

doi:10.1107/S1600536809033728

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2257

doi:10.1107/S1600536809033728

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4-[(2-Hydroxy-1-naphthyl)(piperidin-1-yl)methyl]benzonitrile

Yuan Zhang ^a and Yong Hua Li ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical, Engineering, Southeast UniVersity, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: liyh@seu.edu.cn

(Received 10 June 2009; accepted 24 August 2009; online 29 August 2009)

In the title compound, C₂₃H₂₂N₂O, obtained from the condensation reaction of 4-formylbenzonitrile, 2-naphthol and piperidine, the dihedral angle between the naphthalene ring system and the benzene ring is 75.31 (4)°. The piperidine ring adopts a chair conformation. The crystal structure is stabilized by intermolecular C—H⋯N hydrogen bonds, which link the molecules into centrosymmetric dimers. An intramolecular O—H⋯N hydrogen bond is also present.

Related literature

For applications of Betti-type reactions, see: Zhao & Li et al. (2004 ); Lu et al. (2002 ); Xu et al. (2004 ); Wang et al. (2005 )

Experimental

Crystal data

C₂₃H₂₂N₂O
M_r = 342.43
Monoclinic, P 2₁ /c
a = 6.9989 (6) Å
b = 15.588 (1) Å
c = 17.211 (1) Å
β = 101.207 (2)°
V = 1841.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.2 × 0.1 × 0.1 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear, Rigaku, 2005 ) T_min = 0.98, T_max = 0.98
10945 measured reflections
3245 independent reflections
2661 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.108
S = 1.05
3245 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.99	1.70	2.614	151
C14—H14⋯N1ⁱ	0.93	2.55	3.395 (2)	151
Symmetry code: (i) -x+2, -y, -z+2.

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/PC (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXTL/PC.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809033728/lx2110sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033728/lx2110Isup2.hkl

checkCIF report

Comment top

Over one hundred years ago, Betti developed a straightforward synthesis involving the condensation of 2-naphthol, ammonia and equivalents of benzaldehyde, followed by the addition of HCl and KOH to yield 1-(a-aminobenzyl)-2-naphthol. This product which possesses an asymmetric carbon center is known as a Betti base (Zhao & Li et al. 2004). 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). Here we report the synthesis and crystal structure of the title compound, 4-[(2-hydroxy-1-naphthyl)(1-piperidinyl)methyl]benzonitrile (Fig. 1).

The naphthalene (A; C1-C10), benzene (B; C12-C17) and piperidine (C; N2/C19-C23) rings are planar and the dihedral angles between A/B, A/C, and B/C are 75.31 (4)°, 67.24 (5)°, and 88.80 (5)°, respectively. The crystal structure (Fig. 2) is stabilized by intermolecular C–H···N hydrogen bonds between an H atom of benzene ring and the N atom of the nitrile group, with a C14–H14···N1i (Table 1 and Fig. 2), which link the molecules into centrosymmetric dimers. In addition, the crystal structure exhibits an intramolecular O–H···N hydrogen bond, with a O1–H1···N2 (Table 1 and Fig. 2).

Related literature top

For applications of Betti-type reactions, see: Zhao & Li et al. (2004); Lu et al. (2002); Xu et al. (2004); Wang et al. (2005)

Experimental top

4-Formylbenzonitrile (1.97 g, 0.015 mol) and piperidine (1.275 g, 0.015 mol) was added to 2-naphthol (2.16 g, 0.015 mol) without solvent under nitrogen. The temperature was raised to 120°C in one hour gradually and the mixture was stirred at this temperature for 10 h. The system was treated with 20 ml of ethanol 95% and cooled. The precipitate was filtered and washed with a small amount of ethanol 95%. The title compound was isolated using column chromatography (Petroleum ether: ethyl acetate-4:1). Single crystals suitable for X-ray diffraction analysis were obtained from slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Figures top

	Fig. 1. Perspective structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. C–H···N and O–H···N hydrogen bonds (dotted lines) in the crystal structure of the title compound. [Symmetry code : (i) - x + 2, - y, - z + 2.]

4-[(2-Hydroxy-1-naphthyl)(piperidin-1-yl)methyl]benzonitrile top

Crystal data top

C₂₃H₂₂N₂O	F(000) = 728
M_r = 342.43	D_x = 1.235 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3760 reflections
a = 6.9989 (6) Å	θ = 2.1–26.0°
b = 15.588 (1) Å	µ = 0.08 mm⁻¹
c = 17.211 (1) Å	T = 296 K
β = 101.207 (2)°	Prism, colorless
V = 1841.9 (3) Å³	0.2 × 0.1 × 0.1 mm
Z = 4

Data collection top

Rigaku SCXmini diffractometer	3245 independent reflections
Radiation source: fine-focus sealed tube	2661 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
CCD_Profile_fitting scans	θ_max = 26.0°, θ_min = 2.4°
Absorption correction: multi-scan (CrystalClear, Rigaku, 2005)	h = −6→8
T_min = 0.98, T_max = 0.98	k = −19→18
10945 measured reflections	l = −21→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: difference Fourier map
wR(F²) = 0.108	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0474P)² + 0.2574P] where P = (F_o² + 2F_c²)/3
3245 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₂₃H₂₂N₂O	V = 1841.9 (3) Å³
M_r = 342.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.9989 (6) Å	µ = 0.08 mm⁻¹
b = 15.588 (1) Å	T = 296 K
c = 17.211 (1) Å	0.2 × 0.1 × 0.1 mm
β = 101.207 (2)°

Data collection top

Rigaku SCXmini diffractometer	3245 independent reflections
Absorption correction: multi-scan (CrystalClear, Rigaku, 2005)	2661 reflections with I > 2σ(I)
T_min = 0.98, T_max = 0.98	R_int = 0.023
10945 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.05	Δρ_max = 0.15 e Å⁻³
3245 reflections	Δρ_min = −0.13 e Å⁻³
227 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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

	x	y	z	U_iso*/U_eq
C1	0.4754 (2)	0.29551 (10)	0.68027 (8)	0.0440 (4)
C2	0.3079 (2)	0.33944 (11)	0.68632 (9)	0.0530 (4)
C3	0.1365 (2)	0.32981 (13)	0.62827 (11)	0.0654 (5)
H3	0.0261	0.3612	0.6326	0.078*
C4	0.1307 (2)	0.27582 (13)	0.56662 (10)	0.0646 (5)
H4	0.0163	0.2705	0.5290	0.078*
C5	0.2951 (2)	0.22744 (11)	0.55839 (9)	0.0525 (4)
C6	0.2914 (3)	0.16868 (12)	0.49529 (10)	0.0660 (5)
H6	0.1773	0.1627	0.4577	0.079*
C7	0.4480 (3)	0.12125 (12)	0.48807 (10)	0.0699 (5)
H7	0.4413	0.0827	0.4464	0.084*
C8	0.6191 (3)	0.13057 (12)	0.54346 (10)	0.0653 (5)
H8	0.7275	0.0980	0.5386	0.078*
C9	0.6308 (2)	0.18670 (10)	0.60497 (9)	0.0539 (4)
H9	0.7479	0.1918	0.6410	0.065*
C10	0.4703 (2)	0.23747 (10)	0.61557 (8)	0.0444 (4)
C11	0.6626 (2)	0.30548 (9)	0.74220 (8)	0.0413 (3)
H11	0.7723	0.2984	0.7150	0.050*
C12	0.6784 (2)	0.23582 (9)	0.80461 (8)	0.0420 (3)
C13	0.8360 (2)	0.18047 (11)	0.81721 (9)	0.0552 (4)
H13	0.9315	0.1863	0.7868	0.066*
C14	0.8543 (3)	0.11701 (11)	0.87378 (10)	0.0616 (5)
H14	0.9603	0.0799	0.8809	0.074*
C15	0.7144 (2)	0.10873 (10)	0.92003 (9)	0.0508 (4)
C16	0.5568 (2)	0.16398 (10)	0.90883 (9)	0.0524 (4)
H16	0.4634	0.1593	0.9404	0.063*
C17	0.5384 (2)	0.22595 (10)	0.85088 (9)	0.0487 (4)
H17	0.4301	0.2618	0.8426	0.058*
C18	0.7349 (2)	0.04403 (12)	0.98061 (10)	0.0602 (4)
C19	0.8407 (2)	0.39901 (10)	0.84592 (9)	0.0522 (4)
H19A	0.9609	0.3843	0.8290	0.063*
H19B	0.8212	0.3579	0.8860	0.063*
C20	0.8583 (3)	0.48792 (11)	0.88137 (10)	0.0648 (5)
H20A	0.9686	0.4897	0.9253	0.078*
H20B	0.7419	0.5010	0.9018	0.078*
C21	0.8851 (3)	0.55474 (11)	0.82047 (10)	0.0667 (5)
H21A	0.8842	0.6117	0.8431	0.080*
H21B	1.0093	0.5463	0.8046	0.080*
C22	0.7218 (3)	0.54656 (11)	0.74953 (11)	0.0644 (5)
H22A	0.7440	0.5860	0.7086	0.077*
H22B	0.5997	0.5621	0.7645	0.077*
C23	0.70745 (10)	0.45642 (4)	0.71727 (4)	0.0536 (4)
H23A	0.5997	0.4530	0.6724	0.064*
H23B	0.8260	0.4425	0.6987	0.064*
O1	0.29677 (10)	0.39454 (4)	0.74661 (4)	0.0697 (4)
H1	0.4335	0.4016	0.7749	0.094 (7)*
N1	0.75228 (10)	−0.00682 (4)	1.02933 (4)	0.0807 (5)
N2	0.67754 (10)	0.39314 (4)	0.77784 (4)	0.0440 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0432 (8)	0.0496 (9)	0.0387 (8)	0.0036 (7)	0.0065 (6)	0.0061 (7)
C2	0.0494 (9)	0.0591 (10)	0.0518 (9)	0.0081 (7)	0.0131 (7)	0.0037 (8)
C3	0.0420 (9)	0.0822 (13)	0.0717 (12)	0.0114 (8)	0.0105 (8)	0.0137 (10)
C4	0.0477 (10)	0.0830 (13)	0.0578 (10)	−0.0052 (9)	−0.0029 (8)	0.0136 (10)
C5	0.0512 (9)	0.0594 (11)	0.0440 (8)	−0.0103 (8)	0.0023 (7)	0.0102 (8)
C6	0.0754 (12)	0.0720 (12)	0.0439 (9)	−0.0245 (10)	−0.0050 (8)	0.0024 (9)
C7	0.0973 (15)	0.0600 (12)	0.0518 (10)	−0.0129 (11)	0.0128 (10)	−0.0106 (9)
C8	0.0822 (13)	0.0589 (11)	0.0544 (10)	0.0052 (9)	0.0123 (9)	−0.0108 (9)
C9	0.0580 (10)	0.0560 (10)	0.0459 (9)	0.0041 (8)	0.0055 (7)	−0.0043 (8)
C10	0.0487 (8)	0.0459 (9)	0.0378 (8)	−0.0035 (7)	0.0062 (6)	0.0065 (7)
C11	0.0429 (8)	0.0429 (8)	0.0385 (7)	0.0048 (6)	0.0086 (6)	−0.0007 (6)
C12	0.0470 (8)	0.0397 (8)	0.0369 (7)	0.0018 (6)	0.0023 (6)	−0.0046 (6)
C13	0.0564 (10)	0.0612 (11)	0.0494 (9)	0.0161 (8)	0.0139 (7)	0.0094 (8)
C14	0.0642 (11)	0.0632 (11)	0.0571 (10)	0.0230 (9)	0.0108 (9)	0.0128 (9)
C15	0.0601 (10)	0.0470 (9)	0.0418 (8)	0.0005 (7)	0.0015 (7)	0.0024 (7)
C16	0.0587 (10)	0.0518 (10)	0.0476 (9)	−0.0017 (8)	0.0122 (7)	0.0020 (7)
C17	0.0518 (9)	0.0440 (9)	0.0504 (9)	0.0058 (7)	0.0099 (7)	0.0015 (7)
C18	0.0642 (11)	0.0609 (11)	0.0526 (10)	0.0036 (8)	0.0042 (8)	0.0089 (9)
C19	0.0622 (10)	0.0503 (9)	0.0417 (8)	−0.0038 (8)	0.0040 (7)	0.0016 (7)
C20	0.0842 (13)	0.0561 (11)	0.0537 (10)	−0.0122 (9)	0.0126 (9)	−0.0089 (8)
C21	0.0853 (13)	0.0460 (10)	0.0701 (11)	−0.0093 (9)	0.0186 (10)	−0.0056 (9)
C22	0.0784 (12)	0.0445 (10)	0.0725 (11)	0.0058 (8)	0.0204 (10)	0.0086 (9)
C23	0.0667 (10)	0.0486 (9)	0.0453 (9)	0.0064 (8)	0.0101 (7)	0.0076 (7)
O1	0.0583 (8)	0.0808 (9)	0.0726 (8)	0.0192 (6)	0.0193 (6)	−0.0094 (7)
N1	0.0778 (11)	0.0886 (12)	0.0752 (10)	0.0136 (9)	0.0138 (9)	0.0347 (10)
N2	0.0529 (7)	0.0407 (7)	0.0382 (6)	0.0048 (5)	0.0081 (6)	0.0009 (5)

Geometric parameters (Å, º) top

C1—C2	1.379 (2)	C14—C15	1.383 (2)
C1—C10	1.430 (2)	C14—H14	0.9300
C1—C11	1.528 (2)	C15—C16	1.384 (2)
C2—O1	1.3609 (2)	C15—C18	1.438 (2)
C2—C3	1.412 (2)	C16—C17	1.377 (2)
C3—C4	1.348 (2)	C16—H16	0.9300
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.406 (2)	C18—N1	1.1430 (18)
C4—H4	0.9300	C19—N2	1.4713 (16)
C5—C6	1.417 (2)	C19—C20	1.510 (2)
C5—C10	1.424 (2)	C19—H19A	0.9700
C6—C7	1.348 (3)	C19—H19B	0.9700
C6—H6	0.9300	C20—C21	1.515 (2)
C7—C8	1.386 (3)	C20—H20A	0.9700
C7—H7	0.9300	C20—H20B	0.9700
C8—C9	1.363 (2)	C21—C22	1.507 (2)
C8—H8	0.9300	C21—H21A	0.9700
C9—C10	1.415 (2)	C21—H21B	0.9700
C9—H9	0.9300	C22—C23	1.5069 (18)
C11—N2	1.4931 (2)	C22—H22A	0.9700
C11—C12	1.5163 (19)	C22—H22B	0.9700
C11—H11	0.9800	C23—N2	1.4793
C12—C13	1.384 (2)	C23—H23A	0.9700
C12—C17	1.386 (2)	C23—H23B	0.9700
C13—C14	1.376 (2)	O1—H1	0.9916
C13—H13	0.9300

C2—C1—C10	118.69 (13)	C14—C15—C16	119.78 (14)
C2—C1—C11	121.54 (13)	C14—C15—C18	120.07 (15)
C10—C1—C11	119.74 (12)	C16—C15—C18	120.15 (15)
O1—C2—C1	123.11 (14)	C17—C16—C15	119.83 (15)
O1—C2—C3	116.13 (14)	C17—C16—H16	120.1
C1—C2—C3	120.75 (15)	C15—C16—H16	120.1
C4—C3—C2	121.00 (16)	C16—C17—C12	121.15 (14)
C4—C3—H3	119.5	C16—C17—H17	119.4
C2—C3—H3	119.5	C12—C17—H17	119.4
C3—C4—C5	120.90 (16)	N1—C18—C15	179.28 (18)
C3—C4—H4	119.6	N2—C19—C20	111.64 (13)
C5—C4—H4	119.6	N2—C19—H19A	109.3
C4—C5—C6	122.03 (16)	C20—C19—H19A	109.3
C4—C5—C10	118.90 (15)	N2—C19—H19B	109.3
C6—C5—C10	119.07 (16)	C20—C19—H19B	109.3
C7—C6—C5	122.08 (17)	H19A—C19—H19B	108.0
C7—C6—H6	119.0	C19—C20—C21	111.28 (14)
C5—C6—H6	119.0	C19—C20—H20A	109.4
C6—C7—C8	119.25 (17)	C21—C20—H20A	109.4
C6—C7—H7	120.4	C19—C20—H20B	109.4
C8—C7—H7	120.4	C21—C20—H20B	109.4
C9—C8—C7	121.01 (18)	H20A—C20—H20B	108.0
C9—C8—H8	119.5	C22—C21—C20	109.03 (15)
C7—C8—H8	119.5	C22—C21—H21A	109.9
C8—C9—C10	121.97 (16)	C20—C21—H21A	109.9
C8—C9—H9	119.0	C22—C21—H21B	109.9
C10—C9—H9	119.0	C20—C21—H21B	109.9
C9—C10—C5	116.63 (14)	H21A—C21—H21B	108.3
C9—C10—C1	123.65 (13)	C21—C22—C23	111.30 (13)
C5—C10—C1	119.71 (14)	C21—C22—H22A	109.4
N2—C11—C12	112.00 (10)	C23—C22—H22A	109.4
N2—C11—C1	111.23 (10)	C21—C22—H22B	109.4
C12—C11—C1	110.86 (11)	C23—C22—H22B	109.4
N2—C11—H11	107.5	H22A—C22—H22B	108.0
C12—C11—H11	107.5	N2—C23—C22	111.75 (7)
C1—C11—H11	107.5	N2—C23—H23A	109.3
C13—C12—C17	118.14 (14)	C22—C23—H23A	109.3
C13—C12—C11	120.24 (13)	N2—C23—H23B	109.3
C17—C12—C11	121.61 (13)	C22—C23—H23B	109.3
C14—C13—C12	121.40 (15)	H23A—C23—H23B	107.9
C14—C13—H13	119.3	C2—O1—H1	104.6
C12—C13—H13	119.3	C19—N2—C23	109.00 (7)
C13—C14—C15	119.67 (15)	C19—N2—C11	111.46 (9)
C13—C14—H14	120.2	C23—N2—C11	109.20 (6)
C15—C14—H14	120.2

C10—C1—C2—O1	178.47 (12)	N2—C11—C12—C13	−114.13 (14)
C11—C1—C2—O1	0.41 (2)	C1—C11—C12—C13	121.01 (15)
C10—C1—C2—C3	−2.3 (2)	N2—C11—C12—C17	65.30 (16)
C11—C1—C2—C3	179.62 (14)	C1—C11—C12—C17	−59.56 (17)
O1—C2—C3—C4	−178.99 (15)	C17—C12—C13—C14	0.2 (2)
C1—C2—C3—C4	1.8 (3)	C11—C12—C13—C14	179.64 (15)
C2—C3—C4—C5	0.0 (3)	C12—C13—C14—C15	−1.0 (3)
C3—C4—C5—C6	178.39 (16)	C13—C14—C15—C16	0.3 (3)
C3—C4—C5—C10	−1.2 (2)	C13—C14—C15—C18	−178.43 (16)
C4—C5—C6—C7	−178.88 (17)	C14—C15—C16—C17	1.1 (2)
C10—C5—C6—C7	0.7 (2)	C18—C15—C16—C17	179.81 (14)
C5—C6—C7—C8	−0.7 (3)	C15—C16—C17—C12	−1.8 (2)
C6—C7—C8—C9	0.1 (3)	C13—C12—C17—C16	1.2 (2)
C7—C8—C9—C10	0.4 (3)	C11—C12—C17—C16	−178.23 (13)
C8—C9—C10—C5	−0.3 (2)	C14—C15—C18—N1	90 (16)
C8—C9—C10—C1	178.46 (15)	C16—C15—C18—N1	−89 (16)
C4—C5—C10—C9	179.41 (14)	N2—C19—C20—C21	−57.87 (19)
C6—C5—C10—C9	−0.2 (2)	C19—C20—C21—C22	54.4 (2)
C4—C5—C10—C1	0.6 (2)	C20—C21—C22—C23	−54.38 (19)
C6—C5—C10—C1	−179.01 (14)	C21—C22—C23—N2	57.88 (14)
C2—C1—C10—C9	−177.59 (15)	C20—C19—N2—C23	58.52 (13)
C11—C1—C10—C9	0.5 (2)	C20—C19—N2—C11	179.12 (12)
C2—C1—C10—C5	1.2 (2)	C22—C23—N2—C19	−58.58 (11)
C11—C1—C10—C5	179.26 (13)	C22—C23—N2—C11	179.46 (11)
C2—C1—C11—N2	−30.85 (18)	C12—C11—N2—C19	46.39 (14)
C10—C1—C11—N2	151.10 (12)	C1—C11—N2—C19	171.07 (11)
C2—C1—C11—C12	94.46 (16)	C12—C11—N2—C23	166.88 (8)
C10—C1—C11—C12	−83.59 (16)	C1—C11—N2—C23	−68.46 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.99	1.70	2.614	151
C14—H14···N1ⁱ	0.93	2.55	3.395 (2)	151

Symmetry code: (i) −x+2, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₂N₂O
M_r	342.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	6.9989 (6), 15.588 (1), 17.211 (1)
β (°)	101.207 (2)
V (Å³)	1841.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.2 × 0.1 × 0.1

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear, Rigaku, 2005)
T_min, T_max	0.98, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	10945, 3245, 2661
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.108, 1.05
No. of reflections	3245
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.13

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998), SHELXTL/PC (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.99	1.70	2.614	150.7
C14—H14···N1ⁱ	0.93	2.55	3.395 (2)	150.6

Symmetry code: (i) −x+2, −y, −z+2.

Acknowledgements

This work was supported by a start-up grant (4007041028) and a science technology grant (KJ2009375) from Southeast University to Professor Yong-Hua Li.

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Lu, J., Xu, X. N., Wang, C. D., He, J. G., Hu, Y. F. & Hu, H. W. (2002). Tetrahedron Lett. 43, 8367–8369. Web of Science CrossRef CAS Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, X. Y., Dong, Y. M., Sun, J. W., Xu, X. N., Li, R. & Hu, Y. F. (2005). J. Org. Chem. 70, 1897–1900. Web of Science CrossRef PubMed CAS Google Scholar
Xu, X. N., Lu, J., Dong, Y. M., Li, R., Ge, Z. M. & Hu, Y. F. (2004). Tetrahedron Asymmetry, 15, 475–479. Web of Science CrossRef CSD CAS Google Scholar
Zhao, H., Li, Y. H., Wang, X. S., Qu, Z. R., Wang, L. Z., Xiong, R. G., Abrahams, B. F. & Xue, Z. L. (2004). Chem. Eur. J. 10, 2386–2390. Web of Science CSD CrossRef PubMed CAS Google Scholar