rac-2-Amino-1,2-diphenyl­ethanol

Bari, A.; Al-Obaid, A.M.; Ng, S.W.

doi:10.1107/S1600536812002000

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o491

doi:10.1107/S1600536812002000

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rac-2-Amino-1,2-diphenylethanol

Ahmed Bari,^a Abdulrahman M. Al-Obaid ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 January 2012; accepted 16 January 2012; online 21 January 2012)

In the title compound, C₁₄H₁₅NO, the torsion angle about the two Csp³ atoms adopts a partially eclipsed conformation [−61.5 (1)°]. The dihedral angle between the two rings is 48.1 (1)°. In the crystal, the molecules are connected by O—H⋯N and N—H⋯O hydrogen bonds into zigzag chains running along [010]. One of the amino H atoms is not involved in hydrogen bonding.

Related literature

For the use of chiral 2-amino-1,2-diphenylethan-1-ol in organic synthesis, see: Masters & Hegedus (1993 ); Masters et al. (1991 ).

Experimental

Crystal data

C₁₄H₁₅NO
M_r = 213.27
Monoclinic, C 2/c
a = 26.6096 (6) Å
b = 5.3869 (1) Å
c = 17.1043 (4) Å
β = 114.689 (3)°
V = 2227.66 (8) Å³
Z = 8
Cu Kα radiation
μ = 0.63 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.859, T_max = 0.912
7706 measured reflections
2252 independent reflections
2139 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.085
S = 1.00
2252 reflections
158 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.93 (2)	1.89 (2)	2.813 (1)	172 (2)
N1—H11⋯O1ⁱⁱ	0.91 (2)	2.38 (2)	3.178 (1)	148 (1)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812002000/bt5788sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002000/bt5788Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812002000/bt5788Isup3.cml

checkCIF report

Comment top

Optically active 2-amino-1,2-diphenylethanol is commonly used for palladium-assisted chiral tandem alkylation and carbonylative coupling reactions (Masters & Hegedus, 1993; Masters et al., 1991). The crystal structure of either one of the chiral enantiomers has not been reported although the crystal structures of several 2-ammonium-1,2-diphenylethanol carboxylates have been reported. The crystal structure of the racemic 2-amino-1,2-diphenylethanol (Scheme I) is presented here.

The aromatic rings of the ethyl chain of staggered, the twist being 48.1 (1) ° (Fig. 1). The hydroxy group is hydrogen-bond donor to the amino group of an adjacent molecule; the amino group is hydrogen-bond donor to the hydroxy group of another molecule. The hydrogen bonds generate a linear chain running along [0 1 0] (Table 1). The amino group uses only one H atom to form a hydrogen bond.

Related literature top

For the use of chiral 2-amino-1,2-diphenylethan-1-ol in organic synthesis, see: Masters & Hegedus (1993); Masters et al. (1991).

Experimental top

The compound was obtained commercially, and crystals were grown from its solution in ethanol.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₁₄H₁₅NO at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

rac-2-Amino-1,2-diphenylethanol top

Crystal data top

C₁₄H₁₅NO	F(000) = 912
M_r = 213.27	D_x = 1.272 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 5244 reflections
a = 26.6096 (6) Å	θ = 2.8–74.2°
b = 5.3869 (1) Å	µ = 0.63 mm⁻¹
c = 17.1043 (4) Å	T = 100 K
β = 114.689 (3)°	Prism, colorless
V = 2227.66 (8) Å³	0.25 × 0.20 × 0.15 mm
Z = 8

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2252 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2139 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.015
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.4°, θ_min = 3.7°
ω scan	h = −27→32
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −5→6
T_min = 0.859, T_max = 0.912	l = −21→20
7706 measured 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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0452P)² + 1.7088P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2252 reflections	Δρ_max = 0.30 e Å⁻³
158 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (2)

Crystal data top

C₁₄H₁₅NO	V = 2227.66 (8) Å³
M_r = 213.27	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 26.6096 (6) Å	µ = 0.63 mm⁻¹
b = 5.3869 (1) Å	T = 100 K
c = 17.1043 (4) Å	0.25 × 0.20 × 0.15 mm
β = 114.689 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2252 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2139 reflections with I > 2σ(I)
T_min = 0.859, T_max = 0.912	R_int = 0.015
7706 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.30 e Å⁻³
2252 reflections	Δρ_min = −0.21 e Å⁻³
158 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.54033 (3)	0.71776 (14)	0.48409 (4)	0.01865 (19)
N1	0.49273 (3)	0.74451 (17)	0.59788 (6)	0.0188 (2)
C1	0.57362 (4)	0.64493 (18)	0.57066 (6)	0.0155 (2)
H1A	0.5680	0.4635	0.5765	0.019*
C2	0.55297 (4)	0.78952 (18)	0.62945 (6)	0.0158 (2)
H2	0.5593	0.9708	0.6247	0.019*
C3	0.63447 (4)	0.68973 (18)	0.59384 (6)	0.0153 (2)
C4	0.65167 (4)	0.89815 (19)	0.56318 (6)	0.0178 (2)
H4	0.6251	1.0145	0.5278	0.021*
C5	0.70746 (4)	0.93689 (19)	0.58397 (6)	0.0192 (2)
H5	0.7188	1.0799	0.5630	0.023*
C6	0.74672 (4)	0.7676 (2)	0.63521 (6)	0.0195 (2)
H6	0.7848	0.7934	0.6487	0.023*
C7	0.73012 (4)	0.56042 (19)	0.66658 (6)	0.0205 (2)
H7	0.7568	0.4444	0.7020	0.025*
C8	0.67424 (4)	0.52294 (19)	0.64605 (6)	0.0179 (2)
H8	0.6631	0.3815	0.6680	0.021*
C9	0.58301 (4)	0.71185 (18)	0.72263 (6)	0.0155 (2)
C10	0.62569 (4)	0.85732 (19)	0.77983 (6)	0.0187 (2)
H10	0.6360	1.0050	0.7599	0.022*
C11	0.65356 (4)	0.7899 (2)	0.86577 (6)	0.0222 (2)
H11A	0.6827	0.8911	0.9040	0.027*
C12	0.63889 (4)	0.5752 (2)	0.89591 (6)	0.0215 (2)
H12A	0.6576	0.5300	0.9548	0.026*
C13	0.59667 (4)	0.42707 (19)	0.83945 (7)	0.0208 (2)
H13	0.5866	0.2794	0.8597	0.025*
C14	0.56900 (4)	0.49391 (19)	0.75318 (6)	0.0187 (2)
H14	0.5404	0.3905	0.7148	0.022*
H1	0.5299 (6)	0.572 (3)	0.4526 (11)	0.044 (4)*
H11	0.4750 (6)	0.857 (3)	0.5560 (9)	0.029 (3)*
H12	0.4821 (6)	0.777 (3)	0.6421 (9)	0.029 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0175 (3)	0.0230 (4)	0.0130 (3)	−0.0004 (3)	0.0041 (3)	0.0008 (3)
N1	0.0144 (4)	0.0250 (5)	0.0170 (4)	0.0014 (3)	0.0066 (3)	0.0016 (3)
C1	0.0156 (4)	0.0167 (5)	0.0133 (4)	−0.0006 (4)	0.0052 (4)	0.0004 (3)
C2	0.0149 (5)	0.0162 (5)	0.0165 (5)	−0.0004 (3)	0.0067 (4)	0.0005 (3)
C3	0.0169 (5)	0.0171 (5)	0.0126 (4)	−0.0008 (4)	0.0069 (4)	−0.0029 (3)
C4	0.0183 (5)	0.0176 (5)	0.0166 (4)	0.0008 (4)	0.0064 (4)	0.0010 (4)
C5	0.0212 (5)	0.0192 (5)	0.0183 (5)	−0.0036 (4)	0.0094 (4)	−0.0003 (4)
C6	0.0156 (5)	0.0241 (5)	0.0196 (5)	−0.0015 (4)	0.0082 (4)	−0.0021 (4)
C7	0.0186 (5)	0.0221 (5)	0.0204 (5)	0.0039 (4)	0.0077 (4)	0.0028 (4)
C8	0.0202 (5)	0.0172 (5)	0.0179 (5)	0.0001 (4)	0.0097 (4)	0.0012 (4)
C9	0.0154 (4)	0.0175 (5)	0.0162 (5)	0.0027 (4)	0.0090 (4)	−0.0003 (4)
C10	0.0202 (5)	0.0189 (5)	0.0188 (5)	−0.0012 (4)	0.0099 (4)	−0.0007 (4)
C11	0.0208 (5)	0.0274 (5)	0.0176 (5)	−0.0015 (4)	0.0073 (4)	−0.0032 (4)
C12	0.0221 (5)	0.0288 (6)	0.0156 (5)	0.0067 (4)	0.0097 (4)	0.0031 (4)
C13	0.0239 (5)	0.0204 (5)	0.0231 (5)	0.0038 (4)	0.0148 (4)	0.0040 (4)
C14	0.0187 (5)	0.0188 (5)	0.0205 (5)	−0.0003 (4)	0.0101 (4)	−0.0007 (4)

Geometric parameters (Å, º) top

O1—C1	1.4266 (11)	C6—C7	1.3878 (14)
O1—H1	0.928 (18)	C6—H6	0.9500
N1—C2	1.4822 (12)	C7—C8	1.3926 (14)
N1—H11	0.907 (15)	C7—H7	0.9500
N1—H12	0.927 (15)	C8—H8	0.9500
C1—C3	1.5169 (13)	C9—C10	1.3903 (14)
C1—C2	1.5433 (13)	C9—C14	1.3974 (14)
C1—H1A	1.0000	C10—C11	1.3900 (14)
C2—C9	1.5133 (12)	C10—H10	0.9500
C2—H2	1.0000	C11—C12	1.3867 (15)
C3—C8	1.3910 (14)	C11—H11A	0.9500
C3—C4	1.3947 (14)	C12—C13	1.3877 (15)
C4—C5	1.3903 (14)	C12—H12A	0.9500
C4—H4	0.9500	C13—C14	1.3934 (14)
C5—C6	1.3881 (14)	C13—H13	0.9500
C5—H5	0.9500	C14—H14	0.9500

C1—O1—H1	105.9 (10)	C7—C6—H6	120.2
C2—N1—H11	107.7 (9)	C5—C6—H6	120.2
C2—N1—H12	108.9 (8)	C6—C7—C8	119.86 (9)
H11—N1—H12	106.3 (12)	C6—C7—H7	120.1
O1—C1—C3	111.09 (7)	C8—C7—H7	120.1
O1—C1—C2	107.56 (7)	C3—C8—C7	120.93 (9)
C3—C1—C2	112.40 (8)	C3—C8—H8	119.5
O1—C1—H1A	108.6	C7—C8—H8	119.5
C3—C1—H1A	108.6	C10—C9—C14	118.53 (9)
C2—C1—H1A	108.6	C10—C9—C2	120.14 (9)
N1—C2—C9	110.70 (8)	C14—C9—C2	121.33 (9)
N1—C2—C1	107.78 (7)	C11—C10—C9	121.00 (10)
C9—C2—C1	111.81 (8)	C11—C10—H10	119.5
N1—C2—H2	108.8	C9—C10—H10	119.5
C9—C2—H2	108.8	C10—C11—C12	120.15 (10)
C1—C2—H2	108.8	C10—C11—H11A	119.9
C8—C3—C4	118.71 (9)	C12—C11—H11A	119.9
C8—C3—C1	120.51 (9)	C13—C12—C11	119.52 (9)
C4—C3—C1	120.78 (9)	C13—C12—H12A	120.2
C5—C4—C3	120.50 (9)	C11—C12—H12A	120.2
C5—C4—H4	119.7	C12—C13—C14	120.29 (10)
C3—C4—H4	119.7	C12—C13—H13	119.9
C4—C5—C6	120.30 (9)	C14—C13—H13	119.9
C4—C5—H5	119.8	C13—C14—C9	120.50 (9)
C6—C5—H5	119.8	C13—C14—H14	119.7
C7—C6—C5	119.68 (9)	C9—C14—H14	119.7

O1—C1—C2—N1	54.01 (9)	C1—C3—C8—C7	178.98 (9)
C3—C1—C2—N1	176.61 (8)	C6—C7—C8—C3	0.44 (15)
O1—C1—C2—C9	175.90 (7)	N1—C2—C9—C10	−139.20 (9)
C3—C1—C2—C9	−61.50 (10)	C1—C2—C9—C10	100.61 (10)
O1—C1—C3—C8	−142.45 (9)	N1—C2—C9—C14	41.13 (12)
C2—C1—C3—C8	96.96 (10)	C1—C2—C9—C14	−79.06 (11)
O1—C1—C3—C4	37.40 (12)	C14—C9—C10—C11	−0.70 (14)
C2—C1—C3—C4	−83.18 (10)	C2—C9—C10—C11	179.61 (9)
C8—C3—C4—C5	0.49 (14)	C9—C10—C11—C12	−0.23 (15)
C1—C3—C4—C5	−179.37 (9)	C10—C11—C12—C13	0.73 (15)
C3—C4—C5—C6	0.34 (15)	C11—C12—C13—C14	−0.30 (15)
C4—C5—C6—C7	−0.79 (15)	C12—C13—C14—C9	−0.65 (15)
C5—C6—C7—C8	0.40 (15)	C10—C9—C14—C13	1.14 (14)
C4—C3—C8—C7	−0.88 (14)	C2—C9—C14—C13	−179.18 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.93 (2)	1.89 (2)	2.813 (1)	172 (2)
N1—H11···O1ⁱⁱ	0.91 (2)	2.38 (2)	3.178 (1)	148 (1)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅NO
M_r	213.27
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	26.6096 (6), 5.3869 (1), 17.1043 (4)
β (°)	114.689 (3)
V (Å³)	2227.66 (8)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.859, 0.912
No. of measured, independent and observed [I > 2σ(I)] reflections	7706, 2252, 2139
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.085, 1.00
No. of reflections	2252
No. of parameters	158
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.21

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.93 (2)	1.89 (2)	2.813 (1)	172 (2)
N1—H11···O1ⁱⁱ	0.91 (2)	2.38 (2)	3.178 (1)	148 (1)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1.

Acknowledgements

We thank the Research Center of Pharmacy, King Saud University, and the Ministry of Higher Education of Malaysia (grant No. UM·C/HIR/MOHE/SC/12) for supporting this study.

References

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