erythro-2-Piperidinyl-1,2-di­phenylethanol

Ocak, N.; Kazak, C.; Öztürk, S.; Zerrin, C.; Arsu, N.; Fun, H.-K.; Erdönmez, A.

doi:10.1107/S1600536802016513

erythro-2-Piperidinyl-1,2-diphenylethanol

N. Ocak, C. Kazak, S. Öztürk, C. Zerrin, N. Arsu, H.-K. Fun and A. Erdönmez

The molecule of the title compound, C₁₉H₂₃NO, contains two phenyl rings and a piperidinyl ring. The dihedral angle between the phenyl rings is 40.99 (5)°. The piperidine ring has a chair conformation. There is an intramolecular O—H

N hydrogen bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802016513/cv6145sup1.cif Contains datablocks nn2m, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802016513/cv6145Isup2.hkl Contains datablock I

CCDC reference: 198963

checkCIF report

Key indicators

Single-crystal X-ray study
T = 183 K
Mean (C-C) = 0.002 Å
R factor = 0.058
wR factor = 0.136
Data-to-parameter ratio = 20.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

Comment top

During the process of UV-radiation curing there is an oxygen as a free radical in the medium. To overcome the negative effect caused by the oxygen, we synthesized erythro-2-piperidinyl-1,2 diphenyl ethanol to use it as a hydrogen donor for Type II initiators (Davidson, 1999). In this paper we report the structure of erythro-2-piperidinyl-1,2 diphenyl ethanol, (I). An ORTEPIII (Burnett & Johnson, 1996) plot of compound is shown in Fig.1.

The C6—N1 and C1—N1 bond distances are 1.4749 (19) and 1.4730 (18) Å, respectively, which are similar to the corresponding bond lengths in ethyl 4-{2-[1-(6-methyl-3-pyridazinyl)-4-piperidinyl]ethoxy}benzoate [1.467 (5) and 1.472 (4) Å; Jottier et al., 1991] and 3-{2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl} −2,9-dimethyl]-4H-pyrido[1,2-alpyrimidin-4-one (Ocaperidone) [1.477 (9) and 1.463 (9) Å; Jottier et al., 1992]. The C7—N1, C7—C14 and C14—O2 bond distances are 1.4872 (17) 1.5563 (19) and 1.4286 (17) Å, respectively, which are similar to the corresponding bond lengths in N-(2-Hydroxyethyl)-piperidine, N-(2-Hydroxyethyl)morpholine and N-(2-Hydroxyethyl)piperazine [1.495 (4), 1.493 (4) and 1.397 (4) Å, respectively; Castellari & Sabatino, 1996]. The erythro-2-piperidinyl-1,2 diphenyl ethanol molecule contains three ring systems: two phenyl rings and a piperidinyl ring. For the piperidinyl ring we calculated, following the method of Cremer & Pople (1975), a phase angle θ₂ =2.15 (17)° and ϕ₂ =34 (5)°, indicating a chair conformation, and a puckering amplitude Q=0.5814 (17) Å.

There is an intramolecular O2—H2A···N1 hydrogen bond (Table 1).

Experimental top

Erythro-2-piperidinyl-1,2-diphenyl ethanol: 1 g of trans-stilbene oxide and 1 molar equivalent of distilled piperidine was refluxed for 12 h with vigorous stirring. The product was extracted with diethyl ether and excess morpholine was separated by the addition of 5 ml of distilled water. The combined organic layers were washed with distilled water several times. The solution was dried over anhydrous magnesium sulfate. The crude product was recrystallized from ethanol. M.p:373 K Analysis calculated for C₁₉H₂₃NO: C,81.14; H, 8.18; N, 4.98. Found C, 81.22; H, 8.19; N,5.03.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures top

Fig. 1. An ORTEPIII (Burnett & Johnson, 1996). drawing of the title compound showing the atom-numbering scheme. Displacement ellipsoids of non-H atoms are shown at the 50% probability level.

Erythro-2-piperidinyl-1,2-diphenyl ethanol top

Crystal data top

C₁₉H₂₃NO	F(000) = 608
M_r = 281.38	D_x = 1.174 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5874 reflections
a = 13.6624 (10) Å	θ = 3.0–28.3°
b = 5.6452 (10) Å	µ = 0.07 mm⁻¹
c = 20.678 (4) Å	T = 183 K
β = 93.46 (4)°	Block, colourless
V = 1591.9 (4) Å³	0.72 × 0.50 × 0.36 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	2344 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.080
Graphite monochromator	θ_max = 28.3°, θ_min = 3.0°
Detector resolution: 8.33 pixels mm^-1	h = −15→18
ω scans	k = −7→7
9095 measured reflections	l = −27→25
3833 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.136	w = 1/[σ²(F_o²)] where P = (F_o² + 2F_c²)/3
S = 0.81	(Δ/σ)_max < 0.001
3833 reflections	Δρ_max = 0.23 e Å⁻³
191 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.044 (4)

Crystal data top

C₁₉H₂₃NO	V = 1591.9 (4) Å³
M_r = 281.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.6624 (10) Å	µ = 0.07 mm⁻¹
b = 5.6452 (10) Å	T = 183 K
c = 20.678 (4) Å	0.72 × 0.50 × 0.36 mm
β = 93.46 (4)°

Data collection top

Siemens SMART CCD area-detector diffractometer	2344 reflections with I > 2σ(I)
9095 measured reflections	R_int = 0.080
3833 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 0.81	Δρ_max = 0.23 e Å⁻³
3833 reflections	Δρ_min = −0.33 e Å⁻³
191 parameters

Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was −35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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

	x	y	z	U_iso*/U_eq
O2	0.84897 (8)	0.62204 (19)	0.21889 (5)	0.0361 (3)
H2A	0.8125	0.6262	0.1859	0.054*
N1	0.85600 (8)	0.9562 (2)	0.12095 (5)	0.0231 (3)
C1	0.89873 (11)	1.0492 (3)	0.06236 (7)	0.0314 (4)
H1A	0.9613	0.9728	0.0570	0.038*
H1B	0.9104	1.2179	0.0675	0.038*
C2	0.83133 (12)	1.0068 (3)	0.00242 (7)	0.0366 (4)
H2B	0.8614	1.0693	−0.0353	0.044*
H2C	0.8218	0.8379	−0.0038	0.044*
C4	0.69019 (12)	1.0392 (4)	0.07091 (7)	0.0385 (4)
H4A	0.6746	0.8721	0.0668	0.046*
H4B	0.6299	1.1242	0.0775	0.046*
C5	0.73277 (12)	1.1255 (3)	0.00909 (8)	0.0389 (4)
H5A	0.6887	1.0867	−0.0279	0.047*
H5B	0.7409	1.2962	0.0106	0.047*
C6	0.76167 (11)	1.0763 (3)	0.12906 (7)	0.0339 (4)
H6C	0.7731	1.2446	0.1352	0.041*
H6D	0.7330	1.0158	0.1676	0.041*
C7	0.92417 (10)	0.9814 (3)	0.17938 (6)	0.0207 (3)
H7A	0.9321	1.1502	0.1894	0.025*
C8	1.02439 (10)	0.8759 (2)	0.16939 (7)	0.0210 (3)
C9	1.03625 (12)	0.6620 (3)	0.13777 (7)	0.0300 (4)
H9A	0.9815	0.5830	0.1197	0.036*
C10	1.12856 (14)	0.5643 (3)	0.13267 (8)	0.0396 (4)
H10A	1.1353	0.4204	0.1115	0.048*
C11	1.21075 (13)	0.6807 (4)	0.15911 (8)	0.0434 (5)
H11A	1.2727	0.6154	0.1556	0.052*
C12	1.20065 (12)	0.8918 (3)	0.19044 (8)	0.0389 (4)
H12A	1.2557	0.9697	0.2085	0.047*
C13	1.10811 (11)	0.9896 (3)	0.19525 (7)	0.0264 (4)
H13A	1.1020	1.1342	0.2162	0.032*
C14	0.87706 (11)	0.8576 (3)	0.23715 (7)	0.0248 (3)
H14A	0.8178	0.9455	0.2467	0.030*
C15	0.94437 (10)	0.8513 (3)	0.29803 (7)	0.0227 (3)
C16	1.00775 (12)	0.6646 (3)	0.31171 (7)	0.0311 (4)
H16A	1.0090	0.5369	0.2834	0.037*
C17	1.06956 (12)	0.6666 (3)	0.36747 (8)	0.0367 (4)
H17A	1.1121	0.5403	0.3761	0.044*
C18	1.06850 (12)	0.8532 (3)	0.40996 (8)	0.0369 (4)
H18A	1.1100	0.8532	0.4473	0.044*
C19	1.00555 (12)	1.0408 (3)	0.39707 (8)	0.0367 (4)
H19A	1.0045	1.1679	0.4256	0.044*
C20	0.94356 (11)	1.0388 (3)	0.34096 (7)	0.0303 (4)
H20A	0.9011	1.1652	0.3323	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0388 (7)	0.0433 (7)	0.0266 (6)	−0.0190 (5)	0.0054 (5)	−0.0016 (5)
N1	0.0191 (6)	0.0348 (7)	0.0156 (6)	−0.0024 (5)	0.0036 (5)	−0.0026 (5)
C1	0.0252 (8)	0.0450 (10)	0.0242 (8)	−0.0050 (7)	0.0041 (6)	0.0078 (7)
C2	0.0340 (9)	0.0593 (12)	0.0168 (8)	−0.0035 (8)	0.0038 (6)	0.0034 (7)
C4	0.0222 (8)	0.0684 (13)	0.0246 (8)	0.0014 (8)	−0.0001 (7)	−0.0067 (8)
C5	0.0333 (10)	0.0574 (12)	0.0251 (8)	−0.0033 (8)	−0.0069 (7)	0.0023 (8)
C6	0.0237 (8)	0.0551 (11)	0.0228 (8)	0.0072 (7)	−0.0002 (6)	−0.0087 (7)
C7	0.0209 (7)	0.0232 (8)	0.0180 (7)	−0.0018 (5)	0.0021 (5)	−0.0022 (6)
C8	0.0230 (7)	0.0233 (8)	0.0175 (7)	−0.0004 (6)	0.0060 (6)	0.0040 (6)
C9	0.0369 (9)	0.0254 (9)	0.0289 (8)	−0.0028 (6)	0.0124 (7)	−0.0009 (7)
C10	0.0542 (12)	0.0314 (10)	0.0355 (9)	0.0132 (8)	0.0217 (8)	0.0052 (8)
C11	0.0334 (10)	0.0648 (13)	0.0333 (9)	0.0214 (8)	0.0129 (8)	0.0143 (9)
C12	0.0227 (9)	0.0656 (13)	0.0284 (9)	0.0013 (8)	0.0017 (7)	0.0053 (8)
C13	0.0238 (8)	0.0330 (9)	0.0227 (7)	−0.0025 (6)	0.0043 (6)	0.0010 (6)
C14	0.0221 (7)	0.0321 (9)	0.0207 (7)	−0.0026 (6)	0.0059 (6)	−0.0020 (6)
C15	0.0207 (7)	0.0302 (8)	0.0181 (7)	−0.0018 (6)	0.0081 (6)	0.0025 (6)
C16	0.0383 (9)	0.0326 (9)	0.0233 (8)	0.0049 (7)	0.0093 (7)	0.0029 (7)
C17	0.0335 (9)	0.0468 (11)	0.0302 (9)	0.0098 (7)	0.0059 (7)	0.0116 (8)
C18	0.0296 (9)	0.0535 (12)	0.0270 (8)	−0.0048 (8)	−0.0036 (7)	0.0083 (8)
C19	0.0408 (10)	0.0394 (10)	0.0292 (9)	−0.0048 (7)	−0.0028 (7)	−0.0059 (7)
C20	0.0320 (9)	0.0313 (9)	0.0277 (8)	0.0034 (6)	0.0028 (7)	−0.0013 (7)

Geometric parameters (Å, º) top

O2—C14	1.4286 (17)	C8—C13	1.390 (2)
O2—H2A	0.8200	C9—C10	1.386 (2)
N1—C1	1.4730 (18)	C9—H9A	0.9300
N1—C6	1.4749 (19)	C10—C11	1.385 (3)
N1—C7	1.4872 (17)	C10—H10A	0.9300
C1—C2	1.518 (2)	C11—C12	1.367 (2)
C1—H1A	0.9700	C11—H11A	0.9300
C1—H1B	0.9700	C12—C13	1.389 (2)
C2—C5	1.518 (2)	C12—H12A	0.9300
C2—H2B	0.9700	C13—H13A	0.9300
C2—H2C	0.9700	C14—C15	1.5139 (19)
C4—C5	1.516 (2)	C14—H14A	0.9800
C4—C6	1.517 (2)	C15—C20	1.382 (2)
C4—H4A	0.9700	C15—C16	1.383 (2)
C4—H4B	0.9700	C16—C17	1.388 (2)
C5—H5A	0.9700	C16—H16A	0.9300
C5—H5B	0.9700	C17—C18	1.372 (2)
C6—H6C	0.9700	C17—H17A	0.9300
C6—H6D	0.9700	C18—C19	1.380 (2)
C7—C8	1.5187 (19)	C18—H18A	0.9300
C7—C14	1.5563 (19)	C19—C20	1.395 (2)
C7—H7A	0.9800	C19—H19A	0.9300
C8—C9	1.387 (2)	C20—H20A	0.9300

C14—O2—H2A	109.5	C9—C8—C7	122.51 (13)
C1—N1—C6	108.77 (12)	C13—C8—C7	119.61 (13)
C1—N1—C7	111.98 (11)	C10—C9—C8	120.99 (15)
C6—N1—C7	111.87 (11)	C10—C9—H9A	119.5
N1—C1—C2	111.37 (12)	C8—C9—H9A	119.5
N1—C1—H1A	109.4	C11—C10—C9	120.06 (16)
C2—C1—H1A	109.4	C11—C10—H10A	120.0
N1—C1—H1B	109.4	C9—C10—H10A	120.0
C2—C1—H1B	109.4	C12—C11—C10	119.87 (15)
H1A—C1—H1B	108.0	C12—C11—H11A	120.1
C5—C2—C1	110.73 (14)	C10—C11—H11A	120.1
C5—C2—H2B	109.5	C11—C12—C13	119.93 (16)
C1—C2—H2B	109.5	C11—C12—H12A	120.0
C5—C2—H2C	109.5	C13—C12—H12A	120.0
C1—C2—H2C	109.5	C12—C13—C8	121.34 (15)
H2B—C2—H2C	108.1	C12—C13—H13A	119.3
C5—C4—C6	111.25 (13)	C8—C13—H13A	119.3
C5—C4—H4A	109.4	O2—C14—C15	109.76 (12)
C6—C4—H4A	109.4	O2—C14—C7	109.39 (11)
C5—C4—H4B	109.4	C15—C14—C7	112.96 (11)
C6—C4—H4B	109.4	O2—C14—H14A	108.2
H4A—C4—H4B	108.0	C15—C14—H14A	108.2
C2—C5—C4	108.80 (14)	C7—C14—H14A	108.2
C2—C5—H5A	109.9	C20—C15—C16	118.80 (13)
C4—C5—H5A	109.9	C20—C15—C14	119.23 (13)
C2—C5—H5B	109.9	C16—C15—C14	121.97 (13)
C4—C5—H5B	109.9	C15—C16—C17	120.40 (15)
H5A—C5—H5B	108.3	C15—C16—H16A	119.8
N1—C6—C4	111.82 (13)	C17—C16—H16A	119.8
N1—C6—H6C	109.3	C18—C17—C16	120.58 (15)
C4—C6—H6C	109.3	C18—C17—H17A	119.7
N1—C6—H6D	109.3	C16—C17—H17A	119.7
C4—C6—H6D	109.3	C17—C18—C19	119.73 (15)
H6C—C6—H6D	107.9	C17—C18—H18A	120.1
N1—C7—C8	112.18 (11)	C19—C18—H18A	120.1
N1—C7—C14	108.24 (11)	C18—C19—C20	119.64 (16)
C8—C7—C14	110.26 (11)	C18—C19—H19A	120.2
N1—C7—H7A	108.7	C20—C19—H19A	120.2
C8—C7—H7A	108.7	C15—C20—C19	120.84 (14)
C14—C7—H7A	108.7	C15—C20—H20A	119.6
C9—C8—C13	117.81 (14)	C19—C20—H20A	119.6

C6—N1—C1—C2	−59.83 (17)	C10—C11—C12—C13	−0.5 (3)
C7—N1—C1—C2	176.02 (13)	C11—C12—C13—C8	0.8 (2)
N1—C1—C2—C5	59.36 (19)	C9—C8—C13—C12	−0.8 (2)
C1—C2—C5—C4	−55.07 (18)	C7—C8—C13—C12	176.19 (13)
C6—C4—C5—C2	54.21 (19)	N1—C7—C14—O2	51.90 (15)
C1—N1—C6—C4	58.89 (17)	C8—C7—C14—O2	−71.15 (14)
C7—N1—C6—C4	−176.89 (13)	N1—C7—C14—C15	174.47 (12)
C5—C4—C6—N1	−57.5 (2)	C8—C7—C14—C15	51.43 (16)
C1—N1—C7—C8	−52.85 (16)	O2—C14—C15—C20	−149.17 (13)
C6—N1—C7—C8	−175.26 (12)	C7—C14—C15—C20	88.47 (16)
C1—N1—C7—C14	−174.72 (12)	O2—C14—C15—C16	31.64 (19)
C6—N1—C7—C14	62.87 (15)	C7—C14—C15—C16	−90.73 (17)
N1—C7—C8—C9	−41.60 (18)	C20—C15—C16—C17	−0.2 (2)
C14—C7—C8—C9	79.10 (16)	C14—C15—C16—C17	178.95 (14)
N1—C7—C8—C13	141.55 (13)	C15—C16—C17—C18	0.2 (2)
C14—C7—C8—C13	−97.74 (15)	C16—C17—C18—C19	−0.1 (3)
C13—C8—C9—C10	0.6 (2)	C17—C18—C19—C20	0.0 (3)
C7—C8—C9—C10	−176.35 (14)	C16—C15—C20—C19	0.2 (2)
C8—C9—C10—C11	−0.3 (2)	C14—C15—C20—C19	−179.06 (14)
C9—C10—C11—C12	0.2 (3)	C18—C19—C20—C15	0.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1	0.82	2.39	2.774 (2)	109

Experimental details

Crystal data
Chemical formula	C₁₉H₂₃NO
M_r	281.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	183
a, b, c (Å)	13.6624 (10), 5.6452 (10), 20.678 (4)
β (°)	93.46 (4)
V (Å³)	1591.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.72 × 0.50 × 0.36

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9095, 3833, 2344
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.136, 0.81
No. of reflections	3833
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.33

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Selected geometric parameters (Å, º) top

O2—C14	1.4286 (17)	N1—C7	1.4872 (17)
N1—C1	1.4730 (18)	C7—C14	1.5563 (19)
N1—C6	1.4749 (19)

C1—N1—C6	108.77 (12)	C8—C7—C14	110.26 (11)
C1—N1—C7	111.98 (11)	C9—C8—C13	117.81 (14)
C6—N1—C7	111.87 (11)	C9—C8—C7	122.51 (13)
N1—C6—C4	111.82 (13)	O2—C14—C15	109.76 (12)
N1—C7—C8	112.18 (11)	O2—C14—C7	109.39 (11)
N1—C7—C14	108.24 (11)