4-Chloro-2-((1R)-1-{[(R)-(2-chloro­phen­yl)(cyclo­pent­yl)meth­yl]amino}eth­yl)phenol

Zhang, G.-Y.; Yang, T.; Xu, B.-W.; Chen, D.-J.; Wang, W.-H.

doi:10.1107/S1600536808034624

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Pages o2211-o2212

doi:10.1107/S1600536808034624

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4-Chloro-2-((1R)-1-{[(R)-(2-chlorophenyl)(cyclopentyl)methyl]amino}ethyl)phenol

Guang-You Zhang,^a Ting Yang,^a ^* Bao-Wang Xu,^b Di-Juan Chen ^a and Wan-Hui Wang ^c

^aSchool of Chemistry, Jinan University, Jinan 250022, People's Republic of China, ^bQilu Pharmaceutical Co. Ltd, Shandong Province, Shandong 250100, People's Republic of China, and ^cGraduate School of Science and Engineering, Saitama University, 255 Shimo-ohkubo, Sakura, Saitama 338-8570, Japan
^*Correspondence e-mail: yangting365@126.com

(Received 11 October 2008; accepted 23 October 2008; online 25 October 2008)

The title compound, C₂₀H₂₃Cl₂NO, was prepared by condensation of (R)-1-(2-chlorophenyl)-1-cyclopentylmethanamine with 1-(5-chloro-2-hydroxyphenyl)ethanone, resulting in the formation of a new chiral center. The structural analysis confirms the absolute configuration of the title compound and the formation of the (R,R) diastereoisomer. There is an intramolecular O—H⋯N hydrogen bond which stabilizes the conformation of the molecule. The molecules are linked to each other through weak C—H⋯π interactions.

Related literature

For general background, see: Ager et al. (1996 ); Berrisford et al. (1995 ); Cimarelli & Palmieri (1998 ); Cimarelli et al. (2001 , 2002 ); Hayase et al. (1997 ); Nakano et al. (1997 ); Palmieri (1999 , 2000 ); Soai & Niwa (1992 ); Watanabe et al. (1991 ); Xu & Pu (2004 ); Yang et al. (2005 ).

Experimental

Crystal data

C₂₀H₂₃Cl₂NO
M_r = 364.29
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.286 (2) Å
b = 11.539 (2) Å
c = 14.740 (3) Å
V = 1919.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 298 (2) K
0.42 × 0.29 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.869, T_max = 0.941
10145 measured reflections
3573 independent reflections
2761 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.113
S = 1.02
3573 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 1629 Friedel pairs
Flack parameter: 0.03 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.92	2.639 (3)	146
C3—H3⋯Cg1ⁱ	0.93	2.76	3.661 (3)	164
Symmetry code: (i) $[-x+{\script{3\over 2}}, -y+2, z-{\script{1\over 2}}]$ . Cg is the centroid of the C15–C20 benzene ring

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034624/dn2393sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034624/dn2393Isup2.hkl

checkCIF report

Comment top

The synthesis of enantiopure amine alcohols with a variety of functionalities is an important subject of research because this class of compounds has found widespread application in biological systems showing pharmacological activity. These compounds are used as resolving agents, chiral bases and auxiliaries in asymmetric synthesis (Cimarelli et al.,2002), and most have been derived from new readily available natural products (Ager et al.,1996). Chiral aminophenols, which are similar to aminoalcohols, are important building blocks in organic synthesis, and have attracted increasing attention in recent years owing to their effects in asymmetric synthesis and asymmetric induction (Cimarelli et al.,2001; Palmieri, 1999, 2000; Xu & Pu, 2004; Berrisford et al., 1995; Cimarelli & Palmieri, 1998; Hayase et al., 1997; Nakano et al.,1997; Soai et al., 1992; Watanabe et al., 1991).

As part of our continuing studies of chiral aminophenols, we have established the molecular structure of the title compound which was intially synthesized to test its asymmetric catalytic activity. The compound has been prepared by conventional condensation of (R)-1-(2-chlorophenyl)-1-cyclopentylmethanamine with 1-(5-chloro-2-hydroxyphenyl)ethanone, resulting in the formation of a new chiral center as shown in Fig. 1.

The structural analyses confirms the absolute configuration of the title compound and the formation of the (R,R) diastereoisomer. There is an intramolecular O-H···N hydrogen bond which stabilizes the conformation of the molecule. The molecules are linked to each other through weak C-H···π interaction involving the C15-C20 benzene ring (Table 1).

Related literature top

For general background, see: Ager et al. (1996); Berrisford et al. (1995); Cimarelli & Palmieri (1998); Cimarelli et al. (2001, 2002); Hayase et al. (1997); Nakano et al. (1997); Palmieri (1999, 2000); Soai & Niwa (1992); Watanabe et al. (1991); Xu & Pu (2004); Yang et al. (2005).

Experimental top

The title compound were prepared according to the procedure of Yang et al.(2005). (R)-1-(2-chlorophenyl)-1-cyclopentylmethanamine (0.9 mmol) and 1-(5-chloro-2-hydroxyphenyl)ethanone (0.9 mmol) were dissolved in methanol (10 ml) and reacted at room temperature for 48 h. After removal of the solvent, NaBH₄ (4.5 mmol) was added to the solution in THF/ethanol (1:1 v/v, 20 ml) and stirred at 273 K until the solution became colourless. The solvent was then removed under reduced pressure. Water (10 ml)was added to the residue and 1 N HCl was added dropwise until hydrogen production ceased. The mixture was neutralized with aqueous Na₂CO₃, then extracted with CHCl_3,and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. Further purification was carried out by thin-layer silica-gel chromatography (chloroform) to give a colourless solid (yield 83.5%). Crystals of (I) were grown from a n-hexane.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular view of (I) with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radii. H bond is shown as dashed line.

4-Chloro-2-((1R)-1-{[(R)-(2- chlorophenyl)(cyclopentyl)methyl]amino}ethyl)phenol top

Crystal data top

C₂₀H₂₃Cl₂NO	F(000) = 768
M_r = 364.29	D_x = 1.261 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2608 reflections
a = 11.286 (2) Å	θ = 2.2–20.5°
b = 11.539 (2) Å	µ = 0.34 mm⁻¹
c = 14.740 (3) Å	T = 298 K
V = 1919.5 (6) Å³	Block, colourless
Z = 4	0.42 × 0.29 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3573 independent reflections
Radiation source: fine-focus sealed tube	2761 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −13→13
T_min = 0.869, T_max = 0.941	k = −13→11
10145 measured reflections	l = −17→15

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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0486P)² + 0.3378P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3573 reflections	Δρ_max = 0.17 e Å⁻³
219 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1629 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (8)

Crystal data top

C₂₀H₂₃Cl₂NO	V = 1919.5 (6) Å³
M_r = 364.29	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.286 (2) Å	µ = 0.34 mm⁻¹
b = 11.539 (2) Å	T = 298 K
c = 14.740 (3) Å	0.42 × 0.29 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3573 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2761 reflections with I > 2σ(I)
T_min = 0.869, T_max = 0.941	R_int = 0.032
10145 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.113	Δρ_max = 0.17 e Å⁻³
S = 1.02	Δρ_min = −0.22 e Å⁻³
3573 reflections	Absolute structure: Flack (1983), 1629 Friedel pairs
219 parameters	Absolute structure parameter: 0.03 (8)
0 restraints

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

	x	y	z	U_iso*/U_eq
C1	0.4448 (2)	0.9053 (2)	0.71545 (19)	0.0527 (7)
C2	0.5587 (2)	0.9243 (2)	0.68485 (16)	0.0450 (6)
C3	0.5716 (3)	1.0086 (2)	0.61779 (19)	0.0583 (7)
H3	0.6468	1.0242	0.5952	0.070*
C4	0.4774 (3)	1.0688 (3)	0.5843 (2)	0.0662 (9)
H4	0.4891	1.1245	0.5395	0.079*
C5	0.3652 (3)	1.0476 (3)	0.6164 (2)	0.0702 (9)
H5	0.3007	1.0886	0.5939	0.084*
C6	0.3501 (3)	0.9649 (3)	0.6822 (2)	0.0679 (9)
H6	0.2746	0.9494	0.7043	0.082*
C7	0.6676 (2)	0.8606 (2)	0.71942 (18)	0.0494 (7)
H7	0.6412	0.8068	0.7667	0.059*
C8	0.7239 (3)	0.7890 (3)	0.6445 (2)	0.0597 (8)
H8	0.7496	0.8417	0.5963	0.072*
C9	0.8298 (3)	0.7153 (3)	0.6731 (3)	0.0842 (11)
H9A	0.9015	0.7616	0.6749	0.101*
H9B	0.8168	0.6814	0.7324	0.101*
C10	0.8389 (4)	0.6226 (4)	0.6016 (3)	0.1137 (16)
H10A	0.8922	0.6467	0.5536	0.136*
H10B	0.8687	0.5512	0.6278	0.136*
C11	0.7165 (4)	0.6053 (4)	0.5653 (3)	0.1091 (15)
H11A	0.7171	0.6091	0.4995	0.131*
H11B	0.6863	0.5301	0.5834	0.131*
C12	0.6404 (3)	0.6996 (3)	0.6033 (2)	0.0747 (10)
H12A	0.5877	0.6688	0.6493	0.090*
H12B	0.5930	0.7345	0.5557	0.090*
C13	0.7159 (3)	1.0138 (3)	0.83381 (19)	0.0558 (7)
H13	0.6433	1.0529	0.8140	0.067*
C14	0.8106 (4)	1.1051 (3)	0.8523 (2)	0.0835 (11)
H14A	0.8828	1.0677	0.8705	0.125*
H14B	0.7842	1.1557	0.8999	0.125*
H14C	0.8245	1.1494	0.7983	0.125*
C15	0.6889 (3)	0.9446 (3)	0.91861 (19)	0.0537 (7)
C16	0.6008 (3)	0.9804 (3)	0.9767 (2)	0.0606 (8)
H16	0.5558	1.0452	0.9620	0.073*
C17	0.5781 (3)	0.9215 (4)	1.0566 (2)	0.0757 (10)
C18	0.6416 (5)	0.8248 (4)	1.0777 (3)	0.0969 (15)
H18	0.6254	0.7844	1.1308	0.116*
C19	0.7279 (4)	0.7875 (3)	1.0216 (3)	0.0909 (14)
H19	0.7700	0.7207	1.0362	0.109*
C20	0.7551 (3)	0.8472 (3)	0.9425 (2)	0.0669 (9)
Cl1	0.41737 (8)	0.79949 (9)	0.79694 (7)	0.0876 (3)
Cl2	0.47184 (9)	0.97355 (14)	1.13076 (7)	0.1212 (5)
N1	0.75723 (19)	0.9378 (2)	0.76056 (16)	0.0590 (6)
O1	0.8465 (2)	0.8094 (2)	0.89205 (18)	0.0974 (9)
H1A	0.8471	0.8437	0.8433	0.146*
H1	0.7853	0.9784	0.7146	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0501 (16)	0.0547 (17)	0.0533 (16)	−0.0074 (14)	0.0004 (14)	0.0055 (13)
C2	0.0518 (15)	0.0445 (14)	0.0386 (14)	−0.0076 (13)	−0.0041 (12)	−0.0018 (12)
C3	0.0571 (17)	0.0609 (18)	0.0567 (17)	−0.0135 (15)	−0.0047 (15)	0.0086 (15)
C4	0.088 (2)	0.0532 (19)	0.0577 (19)	−0.0095 (18)	−0.0138 (18)	0.0100 (15)
C5	0.074 (2)	0.063 (2)	0.074 (2)	0.0047 (18)	−0.0227 (19)	0.0004 (19)
C6	0.0472 (15)	0.078 (2)	0.079 (2)	−0.0036 (16)	−0.0035 (15)	0.0018 (19)
C7	0.0468 (15)	0.0528 (16)	0.0485 (16)	−0.0063 (13)	−0.0026 (13)	0.0001 (13)
C8	0.0586 (17)	0.0647 (19)	0.0558 (18)	−0.0008 (15)	−0.0021 (15)	−0.0062 (15)
C9	0.0568 (19)	0.093 (3)	0.102 (3)	0.013 (2)	−0.0081 (18)	−0.028 (2)
C10	0.088 (3)	0.124 (3)	0.129 (4)	0.024 (3)	−0.010 (3)	−0.059 (3)
C11	0.098 (3)	0.097 (3)	0.132 (4)	0.014 (3)	−0.008 (3)	−0.052 (3)
C12	0.068 (2)	0.077 (2)	0.079 (2)	0.0014 (19)	−0.0103 (18)	−0.0250 (19)
C13	0.0533 (16)	0.0598 (17)	0.0544 (17)	−0.0024 (15)	−0.0074 (14)	−0.0045 (14)
C14	0.099 (3)	0.082 (2)	0.069 (2)	−0.028 (2)	−0.001 (2)	−0.0123 (19)
C15	0.0525 (16)	0.0569 (17)	0.0516 (16)	−0.0085 (15)	−0.0162 (14)	−0.0034 (14)
C16	0.0534 (17)	0.070 (2)	0.0587 (19)	−0.0094 (16)	−0.0122 (15)	0.0018 (16)
C17	0.070 (2)	0.095 (3)	0.062 (2)	−0.035 (2)	−0.0145 (18)	0.000 (2)
C18	0.145 (4)	0.086 (3)	0.060 (2)	−0.051 (3)	−0.037 (3)	0.013 (2)
C19	0.143 (4)	0.059 (2)	0.071 (3)	−0.007 (2)	−0.057 (3)	0.001 (2)
C20	0.081 (2)	0.059 (2)	0.060 (2)	0.0069 (18)	−0.0332 (18)	−0.0136 (16)
Cl1	0.0671 (5)	0.1041 (7)	0.0916 (6)	−0.0106 (5)	0.0140 (5)	0.0452 (5)
Cl2	0.0834 (6)	0.2043 (14)	0.0759 (6)	−0.0444 (8)	0.0151 (5)	−0.0046 (8)
N1	0.0475 (13)	0.0749 (17)	0.0547 (14)	−0.0100 (13)	−0.0024 (11)	−0.0098 (13)
O1	0.1023 (19)	0.102 (2)	0.0875 (18)	0.0454 (17)	−0.0382 (15)	−0.0257 (16)

Geometric parameters (Å, º) top

C1—C6	1.363 (4)	C11—H11A	0.9700
C1—C2	1.379 (4)	C11—H11B	0.9700
C1—Cl1	1.740 (3)	C12—H12A	0.9700
C2—C3	1.394 (4)	C12—H12B	0.9700
C2—C7	1.520 (4)	C13—N1	1.468 (3)
C3—C4	1.363 (4)	C13—C15	1.515 (4)
C3—H3	0.9300	C13—C14	1.525 (4)
C4—C5	1.373 (5)	C13—H13	0.9800
C4—H4	0.9300	C14—H14A	0.9600
C5—C6	1.371 (5)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—H6	0.9300	C15—C16	1.375 (4)
C7—N1	1.477 (3)	C15—C20	1.394 (4)
C7—C8	1.518 (4)	C16—C17	1.384 (4)
C7—H7	0.9800	C16—H16	0.9300
C8—C12	1.524 (4)	C17—C18	1.363 (6)
C8—C9	1.526 (4)	C17—Cl2	1.730 (4)
C8—H8	0.9800	C18—C19	1.348 (6)
C9—C10	1.504 (5)	C18—H18	0.9300
C9—H9A	0.9700	C19—C20	1.389 (5)
C9—H9B	0.9700	C19—H19	0.9300
C10—C11	1.495 (6)	C20—O1	1.344 (4)
C10—H10A	0.9700	N1—H1	0.8826
C10—H10B	0.9700	O1—H1A	0.8200
C11—C12	1.495 (5)

C6—C1—C2	122.2 (3)	C10—C11—H11A	110.2
C6—C1—Cl1	117.6 (2)	C12—C11—H11B	110.2
C2—C1—Cl1	120.2 (2)	C10—C11—H11B	110.2
C1—C2—C3	116.1 (3)	H11A—C11—H11B	108.5
C1—C2—C7	124.5 (2)	C11—C12—C8	106.7 (3)
C3—C2—C7	119.4 (2)	C11—C12—H12A	110.4
C4—C3—C2	122.1 (3)	C8—C12—H12A	110.4
C4—C3—H3	118.9	C11—C12—H12B	110.4
C2—C3—H3	118.9	C8—C12—H12B	110.4
C3—C4—C5	120.2 (3)	H12A—C12—H12B	108.6
C3—C4—H4	119.9	N1—C13—C15	110.8 (2)
C5—C4—H4	119.9	N1—C13—C14	108.8 (2)
C6—C5—C4	118.9 (3)	C15—C13—C14	110.9 (2)
C6—C5—H5	120.6	N1—C13—H13	108.7
C4—C5—H5	120.6	C15—C13—H13	108.7
C1—C6—C5	120.5 (3)	C14—C13—H13	108.7
C1—C6—H6	119.7	C13—C14—H14A	109.5
C5—C6—H6	119.7	C13—C14—H14B	109.5
N1—C7—C8	109.9 (2)	H14A—C14—H14B	109.5
N1—C7—C2	113.6 (2)	C13—C14—H14C	109.5
C8—C7—C2	111.0 (2)	H14A—C14—H14C	109.5
N1—C7—H7	107.4	H14B—C14—H14C	109.5
C8—C7—H7	107.4	C16—C15—C20	118.2 (3)
C2—C7—H7	107.4	C16—C15—C13	120.0 (3)
C7—C8—C12	113.6 (2)	C20—C15—C13	121.7 (3)
C7—C8—C9	115.5 (3)	C15—C16—C17	121.1 (3)
C12—C8—C9	102.5 (3)	C15—C16—H16	119.4
C7—C8—H8	108.3	C17—C16—H16	119.4
C12—C8—H8	108.3	C18—C17—C16	119.9 (4)
C9—C8—H8	108.3	C18—C17—Cl2	120.3 (3)
C10—C9—C8	104.9 (3)	C16—C17—Cl2	119.8 (3)
C10—C9—H9A	110.8	C19—C18—C17	120.2 (4)
C8—C9—H9A	110.8	C19—C18—H18	119.9
C10—C9—H9B	110.8	C17—C18—H18	119.9
C8—C9—H9B	110.8	C18—C19—C20	121.1 (4)
H9A—C9—H9B	108.8	C18—C19—H19	119.5
C11—C10—C9	106.4 (3)	C20—C19—H19	119.5
C11—C10—H10A	110.4	O1—C20—C19	118.2 (3)
C9—C10—H10A	110.4	O1—C20—C15	122.2 (3)
C11—C10—H10B	110.4	C19—C20—C15	119.5 (4)
C9—C10—H10B	110.4	C13—N1—C7	116.4 (2)
H10A—C10—H10B	108.6	C13—N1—H1	111.2
C12—C11—C10	107.4 (3)	C7—N1—H1	104.5
C12—C11—H11A	110.2	C20—O1—H1A	109.5

C6—C1—C2—C3	0.2 (4)	C7—C8—C12—C11	−154.8 (3)
Cl1—C1—C2—C3	178.3 (2)	C9—C8—C12—C11	−29.4 (4)
C6—C1—C2—C7	179.9 (3)	N1—C13—C15—C16	−148.4 (2)
Cl1—C1—C2—C7	−1.9 (4)	C14—C13—C15—C16	90.6 (3)
C1—C2—C3—C4	0.0 (4)	N1—C13—C15—C20	34.8 (4)
C7—C2—C3—C4	−179.8 (3)	C14—C13—C15—C20	−86.2 (3)
C2—C3—C4—C5	0.0 (5)	C20—C15—C16—C17	−0.1 (4)
C3—C4—C5—C6	−0.2 (5)	C13—C15—C16—C17	−177.1 (3)
C2—C1—C6—C5	−0.3 (5)	C15—C16—C17—C18	−1.6 (5)
Cl1—C1—C6—C5	−178.5 (2)	C15—C16—C17—Cl2	176.6 (2)
C4—C5—C6—C1	0.3 (5)	C16—C17—C18—C19	1.2 (5)
C1—C2—C7—N1	−119.6 (3)	Cl2—C17—C18—C19	−177.0 (3)
C3—C2—C7—N1	60.2 (3)	C17—C18—C19—C20	1.0 (6)
C1—C2—C7—C8	116.1 (3)	C18—C19—C20—O1	176.3 (3)
C3—C2—C7—C8	−64.2 (3)	C18—C19—C20—C15	−2.7 (5)
N1—C7—C8—C12	175.2 (3)	C16—C15—C20—O1	−176.8 (3)
C2—C7—C8—C12	−58.3 (3)	C13—C15—C20—O1	0.1 (4)
N1—C7—C8—C9	57.2 (3)	C16—C15—C20—C19	2.2 (4)
C2—C7—C8—C9	−176.4 (3)	C13—C15—C20—C19	179.1 (3)
C7—C8—C9—C10	158.9 (3)	C15—C13—N1—C7	70.8 (3)
C12—C8—C9—C10	34.8 (4)	C14—C13—N1—C7	−166.9 (3)
C8—C9—C10—C11	−27.7 (5)	C8—C7—N1—C13	179.4 (2)
C9—C10—C11—C12	9.1 (5)	C2—C7—N1—C13	54.4 (3)
C10—C11—C12—C8	13.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.92	2.639 (3)	146
C3—H3···Cg1ⁱ	0.93	2.76	3.661 (3)	164

Symmetry code: (i) −x+3/2, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₃Cl₂NO
M_r	364.29
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	11.286 (2), 11.539 (2), 14.740 (3)
V (Å³)	1919.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.42 × 0.29 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.869, 0.941
No. of measured, independent and observed [I > 2σ(I)] reflections	10145, 3573, 2761
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.113, 1.02
No. of reflections	3573
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.22
Absolute structure	Flack (1983), 1629 Friedel pairs
Absolute structure parameter	0.03 (8)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.92	2.639 (3)	145.5
C3—H3···Cg1ⁱ	0.93	2.76	3.661 (3)	164.0

Symmetry code: (i) −x+3/2, −y+2, z−1/2.

Acknowledgements

The authors are grateful to the Natural Science Foundation of Shandong Province China (grant No. G0231) and the Foundation of the Education Ministry of China for Returned Students (grant No. G0220) for financial support. The X-ray data were collected at Shandong Normal University, China.

References

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Volume 64| Part 11| November 2008| Pages o2211-o2212

doi:10.1107/S1600536808034624

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-Chloro-2-((1R)-1-{[(R)-(2-chloro­phen­yl)(cyclo­pent­yl)meth­yl]amino}eth­yl)phenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-Chloro-2-((1R)-1-{[(R)-(2-chlorophenyl)(cyclopentyl)methyl]amino}ethyl)phenol