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

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

doi:10.1107/S1600536808042025

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o123

doi:10.1107/S1600536808042025

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4-Chloro-2-((1R)-1-{[(R)-(2-chlorophenyl)(cyclopentyl)methyl]amino}propyl)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, 250022, People's Republic of China, ^bQilu Pharmaceutical Co Ltd, Shandong Provience, 250100, People's Republic of China, and ^cGraduate School of Science and Engineering, Saitama University, Sakura, Saitama 338-8570, Japan
^*Correspondence e-mail: yangting365@126.com

(Received 14 November 2008; accepted 10 December 2008; online 13 December 2008)

In the title compound, C₂₁H₂₅Cl₂NO, the dihedral angle between the two benzene rings is 33.18 (11)°. The five-membered ring adopts an envelope conformation. There is an intramolecular O—H⋯N hydrogen bond. In the crystal, molecules are linked by weak N—H⋯Cl hydrogen bonds, forming a helical chain along the c axis.

Related literature

For related literature on aminophenols, see: Cimarelli et al. (2002 ); Joshi & Malhotra (2003 ); Li et al. (2004 ); Puigjaner et al. (1999 ); Watts et al. (2005 ). For the synthesis, see: Yang et al. (2005 ).

Experimental

Crystal data

C₂₁H₂₅Cl₂NO
M_r = 378.32
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.9802 (17) Å
b = 11.5607 (18) Å
c = 15.536 (2) Å
V = 1972.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 298 (2) K
0.49 × 0.45 × 0.38 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.852, T_max = 0.882
10332 measured reflections
3647 independent reflections
3266 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.093
S = 1.03
3647 reflections
231 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ), 1556 Friedel pairs
Flack parameter: 0.06 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl2ⁱ	0.848 (19)	2.913 (13)	3.7023 (18)	156 (2)
O1—H1A⋯N1	0.82	1.93	2.642 (2)	144
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+2, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042025/is2364sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808042025/is2364Isup2.hkl

checkCIF report

Comment top

The synthesis of enantiopure aminophenols that have different functionalities is an important subject of research because compounds of this class are widespread in natural products, show pharmacological activity and have recently found application in asymmetric synthesis as chiral bases, auxiliaries and ligands (Cimarelli et al., 2002). Chiral aminophenols which are similar to amino alcohols have attracted wide attention for the reason that they can be used in catalytic asymmetric reactions (Puigjaner et al., 1999; Li et al., 2004; Watts et al., 2005), which is one of the most active areas of research in organic chemistry (Joshi & Malhotra, 2003). The synthesis of new aminoalkylphenols is therefore of interest because of potential as asymmetric catalysts.

As part of our continuing studies of chiral aminophenols, we now report the crystal structure of the title compound, (I), which was intially prepared to test its asymmetric catalytic activity. These compounds were prepared by conventional condensation of (R)-1-(2-chlorophenyl)-1-cyclopentylmethanamine with 1-(5-chloro-2-hydroxyphenyl)ethanone, followed by reduction using sodium borohydride in a tetrahydrofuran-ethanol (1:1 v/v) mixture. An X-ray study of the title compound, (I), was carried out and the results are presented here. The molecular structure of (I) is shown in Fig. 1.

The molecule has two chiral centres (C7/C10), which have configuration R, R, as shown in Fig. 1. In the molecules of (I), the five-membered rings adopts an envelope conformation. The dihedral angle between the benzene rings is 33.18 (11)°. There is an intramolecular O1—H1A···N1 hydrogen bond (Table 1). Phenol atom O1 acts as a hydrogen bond donor to atom N1, with O1···N1 = 2.647 (2) Å, which indicates a comparatively strong intramolecular hydrogen bond (Table 1); this distance is significantly shorter than the sum (3.07 Å) of the van der Waals radii for N and O atoms. The molecules are linked via N1—H1···Cl2 hydrogen bonds. An interesting feature of the structure is that the N1—H1···Cl2 hydrogen-bond gives rise to a spiral chain of molecules along the c direction. There are no π-π stacking interactions are present in the structure of (I).

Related literature top

For related literature on aminophenols, see: Cimarelli et al. (2002); Joshi & Malhotra (2003); Li et al. (2004); Puigjaner et al. (1999); Watts et al. (2005). For the synthesis, see: 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)propan-1-one (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 CHCl₃, 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 80.5%). Crystals of (I) were grown from a n-hexane solution.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I), showing the atom-labelling schemes. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as spheres of arbitrary radii.
	Fig. 2. A packing diagram of (I), view down the b axis, showing the formation of helical chains through O1—H1A···N1 and N1—H1···Cl2 hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonds have been omitted.

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

Crystal data top

C₂₁H₂₅Cl₂NO	F(000) = 800
M_r = 378.32	D_x = 1.274 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4568 reflections
a = 10.9802 (17) Å	θ = 2.2–25.5°
b = 11.5607 (18) Å	µ = 0.34 mm⁻¹
c = 15.536 (2) Å	T = 298 K
V = 1972.1 (5) Å³	Block, colourless
Z = 4	0.49 × 0.45 × 0.38 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3647 independent reflections
Radiation source: fine-focus sealed tube	3266 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→13
T_min = 0.852, T_max = 0.882	k = −13→13
10332 measured reflections	l = −18→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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.0504P)² + 0.2043P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3647 reflections	Δρ_max = 0.17 e Å⁻³
231 parameters	Δρ_min = −0.20 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1556 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.06 (6)

Crystal data top

C₂₁H₂₅Cl₂NO	V = 1972.1 (5) Å³
M_r = 378.32	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.9802 (17) Å	µ = 0.34 mm⁻¹
b = 11.5607 (18) Å	T = 298 K
c = 15.536 (2) Å	0.49 × 0.45 × 0.38 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3647 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3266 reflections with I > 2σ(I)
T_min = 0.852, T_max = 0.882	R_int = 0.025
10332 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.093	Δρ_max = 0.17 e Å⁻³
S = 1.03	Δρ_min = −0.20 e Å⁻³
3647 reflections	Absolute structure: Flack (1983), 1556 Friedel pairs
231 parameters	Absolute structure parameter: 0.06 (6)
1 restraint

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	0.4025 (2)	0.9204 (2)	0.46157 (14)	0.0567 (6)
C2	0.3358 (3)	0.8241 (2)	0.43935 (15)	0.0695 (7)
H2	0.3513	0.7853	0.3881	0.083*
C3	0.2468 (3)	0.7864 (2)	0.49342 (16)	0.0687 (7)
H3	0.2013	0.7216	0.4786	0.082*
C4	0.2227 (2)	0.84331 (19)	0.57058 (15)	0.0576 (6)
C5	0.29329 (17)	0.93830 (17)	0.59471 (12)	0.0442 (5)
C6	0.38307 (18)	0.97536 (19)	0.53893 (13)	0.0476 (5)
H6	0.4312	1.0384	0.5539	0.057*
C7	0.26917 (18)	1.00349 (17)	0.67807 (13)	0.0453 (5)
H7	0.3437	1.0439	0.6955	0.054*
C8	0.1659 (2)	1.0917 (2)	0.66944 (15)	0.0621 (6)
H8A	0.0917	1.0509	0.6542	0.075*
H8B	0.1528	1.1279	0.7250	0.075*
C9	0.1884 (3)	1.1847 (2)	0.60364 (17)	0.0757 (7)
H9A	0.2633	1.2238	0.6167	0.113*
H9B	0.1225	1.2393	0.6048	0.113*
H9C	0.1937	1.1506	0.5475	0.113*
C10	0.33131 (17)	0.84631 (17)	0.77983 (12)	0.0420 (4)
H10	0.3589	0.7969	0.7324	0.050*
C11	0.27940 (18)	0.76780 (18)	0.84923 (13)	0.0479 (5)
H11	0.2531	0.8162	0.8976	0.057*
C12	0.1718 (2)	0.6922 (2)	0.82169 (16)	0.0626 (6)
H12A	0.0968	0.7366	0.8208	0.075*
H12B	0.1855	0.6594	0.7650	0.075*
C13	0.1665 (3)	0.5979 (3)	0.8899 (2)	0.0886 (9)
H13A	0.1118	0.6201	0.9360	0.106*
H13B	0.1376	0.5261	0.8649	0.106*
C14	0.2942 (2)	0.5833 (2)	0.92374 (19)	0.0737 (7)
H14A	0.3261	0.5080	0.9081	0.088*
H14B	0.2951	0.5901	0.9860	0.088*
C15	0.3705 (2)	0.67875 (19)	0.88315 (15)	0.0563 (5)
H15A	0.4197	0.6482	0.8365	0.068*
H15B	0.4240	0.7135	0.9256	0.068*
C16	0.44189 (17)	0.91271 (16)	0.81295 (12)	0.0405 (4)
C17	0.55907 (18)	0.89656 (17)	0.78285 (13)	0.0466 (5)
C18	0.6565 (2)	0.9581 (2)	0.81494 (16)	0.0596 (6)
H18	0.7342	0.9451	0.7932	0.071*
C19	0.6393 (2)	1.0384 (2)	0.87866 (16)	0.0639 (6)
H19	0.7048	1.0806	0.8999	0.077*
C20	0.5237 (2)	1.0559 (2)	0.91091 (15)	0.0608 (6)
H20	0.5112	1.1094	0.9547	0.073*
C21	0.4275 (2)	0.99458 (18)	0.87846 (14)	0.0522 (5)
H21	0.3501	1.0078	0.9007	0.063*
Cl1	0.58898 (6)	0.79389 (6)	0.70334 (4)	0.0724 (2)
Cl2	0.51106 (6)	0.97523 (8)	0.39044 (4)	0.0820 (2)
N1	0.23430 (14)	0.92140 (16)	0.74620 (11)	0.0469 (4)
H1	0.1982 (19)	0.9534 (18)	0.7882 (11)	0.056*
O1	0.13051 (17)	0.80387 (17)	0.62012 (11)	0.0773 (5)
H1A	0.1323	0.8364	0.6670	0.116*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0571 (12)	0.0642 (14)	0.0489 (12)	0.0175 (12)	−0.0106 (10)	0.0005 (10)
C2	0.100 (2)	0.0584 (14)	0.0502 (13)	0.0194 (14)	−0.0232 (14)	−0.0075 (11)
C3	0.102 (2)	0.0470 (12)	0.0576 (14)	−0.0064 (13)	−0.0373 (14)	0.0001 (12)
C4	0.0675 (14)	0.0481 (11)	0.0570 (13)	−0.0112 (11)	−0.0277 (11)	0.0128 (10)
C5	0.0439 (10)	0.0445 (11)	0.0442 (10)	0.0005 (9)	−0.0147 (8)	0.0040 (8)
C6	0.0458 (11)	0.0477 (11)	0.0491 (11)	0.0033 (9)	−0.0125 (9)	−0.0017 (9)
C7	0.0441 (11)	0.0458 (11)	0.0459 (10)	−0.0009 (8)	−0.0084 (8)	0.0015 (9)
C8	0.0641 (14)	0.0609 (13)	0.0614 (13)	0.0163 (12)	0.0008 (11)	0.0083 (11)
C9	0.100 (2)	0.0566 (14)	0.0705 (15)	0.0221 (15)	0.0023 (15)	0.0104 (12)
C10	0.0412 (10)	0.0434 (10)	0.0414 (10)	0.0026 (8)	−0.0012 (8)	−0.0017 (8)
C11	0.0450 (11)	0.0529 (12)	0.0457 (11)	0.0025 (10)	−0.0024 (8)	0.0038 (9)
C12	0.0482 (12)	0.0691 (14)	0.0706 (15)	−0.0085 (11)	−0.0056 (10)	0.0153 (13)
C13	0.0688 (16)	0.090 (2)	0.107 (2)	−0.0184 (15)	−0.0105 (16)	0.0458 (18)
C14	0.0747 (16)	0.0628 (14)	0.0837 (17)	−0.0079 (14)	−0.0110 (13)	0.0242 (14)
C15	0.0546 (12)	0.0533 (12)	0.0610 (13)	0.0016 (10)	−0.0084 (10)	0.0108 (10)
C16	0.0437 (10)	0.0379 (9)	0.0401 (10)	0.0049 (8)	−0.0029 (8)	0.0018 (8)
C17	0.0470 (11)	0.0439 (10)	0.0488 (11)	0.0027 (9)	−0.0002 (9)	0.0001 (9)
C18	0.0447 (11)	0.0578 (13)	0.0763 (15)	0.0009 (10)	−0.0047 (11)	0.0011 (12)
C19	0.0616 (14)	0.0532 (13)	0.0768 (16)	−0.0082 (11)	−0.0235 (12)	−0.0001 (12)
C20	0.0738 (16)	0.0472 (12)	0.0615 (13)	0.0045 (12)	−0.0138 (12)	−0.0097 (11)
C21	0.0520 (12)	0.0485 (12)	0.0562 (12)	0.0073 (10)	−0.0037 (10)	−0.0068 (9)
Cl1	0.0588 (3)	0.0828 (4)	0.0757 (4)	0.0041 (3)	0.0154 (3)	−0.0274 (3)
Cl2	0.0672 (4)	0.1215 (6)	0.0573 (3)	0.0189 (4)	0.0075 (3)	−0.0007 (4)
N1	0.0392 (9)	0.0552 (10)	0.0463 (9)	0.0065 (8)	−0.0023 (7)	0.0070 (8)
O1	0.0815 (12)	0.0804 (12)	0.0701 (11)	−0.0394 (10)	−0.0257 (10)	0.0165 (10)

Geometric parameters (Å, º) top

C1—C6	1.376 (3)	C11—C12	1.531 (3)
C1—C2	1.377 (4)	C11—H11	0.9800
C1—Cl2	1.745 (3)	C12—C13	1.521 (3)
C2—C3	1.360 (4)	C12—H12A	0.9700
C2—H2	0.9300	C12—H12B	0.9700
C3—C4	1.393 (4)	C13—C14	1.507 (4)
C3—H3	0.9300	C13—H13A	0.9700
C4—O1	1.351 (3)	C13—H13B	0.9700
C4—C5	1.395 (3)	C14—C15	1.522 (3)
C5—C6	1.381 (3)	C14—H14A	0.9700
C5—C7	1.522 (3)	C14—H14B	0.9700
C6—H6	0.9300	C15—H15A	0.9700
C7—N1	1.472 (3)	C15—H15B	0.9700
C7—C8	1.531 (3)	C16—C17	1.382 (3)
C7—H7	0.9800	C16—C21	1.399 (3)
C8—C9	1.504 (3)	C17—C18	1.378 (3)
C8—H8A	0.9700	C17—Cl1	1.744 (2)
C8—H8B	0.9700	C18—C19	1.370 (3)
C9—H9A	0.9600	C18—H18	0.9300
C9—H9B	0.9600	C19—C20	1.379 (3)
C9—H9C	0.9600	C19—H19	0.9300
C10—N1	1.470 (2)	C20—C21	1.369 (3)
C10—C11	1.520 (3)	C20—H20	0.9300
C10—C16	1.526 (3)	C21—H21	0.9300
C10—H10	0.9800	N1—H1	0.848 (19)
C11—C15	1.529 (3)	O1—H1A	0.8200

C6—C1—C2	120.7 (2)	C12—C11—H11	108.2
C6—C1—Cl2	119.43 (19)	C13—C12—C11	104.11 (19)
C2—C1—Cl2	119.89 (19)	C13—C12—H12A	110.9
C3—C2—C1	119.1 (2)	C11—C12—H12A	110.9
C3—C2—H2	120.5	C13—C12—H12B	110.9
C1—C2—H2	120.5	C11—C12—H12B	110.9
C2—C3—C4	121.1 (2)	H12A—C12—H12B	109.0
C2—C3—H3	119.4	C14—C13—C12	106.7 (2)
C4—C3—H3	119.4	C14—C13—H13A	110.4
O1—C4—C3	118.2 (2)	C12—C13—H13A	110.4
O1—C4—C5	121.9 (2)	C14—C13—H13B	110.4
C3—C4—C5	119.8 (2)	C12—C13—H13B	110.4
C6—C5—C4	118.2 (2)	H13A—C13—H13B	108.6
C6—C5—C7	120.31 (17)	C13—C14—C15	106.6 (2)
C4—C5—C7	121.45 (19)	C13—C14—H14A	110.4
C1—C6—C5	121.0 (2)	C15—C14—H14A	110.4
C1—C6—H6	119.5	C13—C14—H14B	110.4
C5—C6—H6	119.5	C15—C14—H14B	110.4
N1—C7—C5	109.75 (16)	H14A—C14—H14B	108.6
N1—C7—C8	107.43 (17)	C14—C15—C11	105.70 (18)
C5—C7—C8	112.60 (16)	C14—C15—H15A	110.6
N1—C7—H7	109.0	C11—C15—H15A	110.6
C5—C7—H7	109.0	C14—C15—H15B	110.6
C8—C7—H7	109.0	C11—C15—H15B	110.6
C9—C8—C7	114.5 (2)	H15A—C15—H15B	108.7
C9—C8—H8A	108.6	C17—C16—C21	116.28 (18)
C7—C8—H8A	108.6	C17—C16—C10	123.98 (17)
C9—C8—H8B	108.6	C21—C16—C10	119.74 (17)
C7—C8—H8B	108.6	C18—C17—C16	122.04 (19)
H8A—C8—H8B	107.6	C18—C17—Cl1	117.49 (16)
C8—C9—H9A	109.5	C16—C17—Cl1	120.46 (15)
C8—C9—H9B	109.5	C19—C18—C17	120.3 (2)
H9A—C9—H9B	109.5	C19—C18—H18	119.9
C8—C9—H9C	109.5	C17—C18—H18	119.9
H9A—C9—H9C	109.5	C18—C19—C20	119.2 (2)
H9B—C9—H9C	109.5	C18—C19—H19	120.4
N1—C10—C11	109.45 (15)	C20—C19—H19	120.4
N1—C10—C16	113.53 (16)	C21—C20—C19	120.0 (2)
C11—C10—C16	111.07 (15)	C21—C20—H20	120.0
N1—C10—H10	107.5	C19—C20—H20	120.0
C11—C10—H10	107.5	C20—C21—C16	122.1 (2)
C16—C10—H10	107.5	C20—C21—H21	119.0
C10—C11—C15	113.65 (17)	C16—C21—H21	119.0
C10—C11—C12	115.59 (17)	C10—N1—C7	116.59 (15)
C15—C11—C12	102.53 (18)	C10—N1—H1	108.9 (16)
C10—C11—H11	108.2	C7—N1—H1	113.1 (16)
C15—C11—H11	108.2	C4—O1—H1A	109.5

C6—C1—C2—C3	2.6 (3)	C11—C12—C13—C14	−27.7 (3)
Cl2—C1—C2—C3	−176.33 (18)	C12—C13—C14—C15	6.6 (3)
C1—C2—C3—C4	−0.2 (3)	C13—C14—C15—C11	17.1 (3)
C2—C3—C4—O1	177.9 (2)	C10—C11—C15—C14	−159.2 (2)
C2—C3—C4—C5	−2.2 (3)	C12—C11—C15—C14	−33.7 (2)
O1—C4—C5—C6	−177.83 (19)	N1—C10—C16—C17	−122.7 (2)
C3—C4—C5—C6	2.2 (3)	C11—C10—C16—C17	113.4 (2)
O1—C4—C5—C7	−0.6 (3)	N1—C10—C16—C21	58.1 (2)
C3—C4—C5—C7	179.43 (19)	C11—C10—C16—C21	−65.8 (2)
C2—C1—C6—C5	−2.6 (3)	C21—C16—C17—C18	−0.5 (3)
Cl2—C1—C6—C5	176.38 (15)	C10—C16—C17—C18	−179.69 (18)
C4—C5—C6—C1	0.1 (3)	C21—C16—C17—Cl1	178.20 (14)
C7—C5—C6—C1	−177.13 (18)	C10—C16—C17—Cl1	−1.0 (3)
C6—C5—C7—N1	−145.10 (17)	C16—C17—C18—C19	0.0 (3)
C4—C5—C7—N1	37.7 (2)	Cl1—C17—C18—C19	−178.73 (18)
C6—C5—C7—C8	95.3 (2)	C17—C18—C19—C20	0.7 (4)
C4—C5—C7—C8	−81.9 (2)	C18—C19—C20—C21	−0.9 (4)
N1—C7—C8—C9	178.4 (2)	C19—C20—C21—C16	0.4 (3)
C5—C7—C8—C9	−60.7 (3)	C17—C16—C21—C20	0.3 (3)
N1—C10—C11—C15	175.01 (17)	C10—C16—C21—C20	179.5 (2)
C16—C10—C11—C15	−58.8 (2)	C11—C10—N1—C7	179.95 (17)
N1—C10—C11—C12	56.8 (2)	C16—C10—N1—C7	55.2 (2)
C16—C10—C11—C12	−177.03 (17)	C5—C7—N1—C10	71.5 (2)
C10—C11—C12—C13	161.7 (2)	C8—C7—N1—C10	−165.80 (17)
C15—C11—C12—C13	37.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl2ⁱ	0.85 (2)	2.91 (1)	3.7023 (18)	156 (2)
O1—H1A···N1	0.82	1.93	2.642 (2)	144

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₅Cl₂NO
M_r	378.32
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	10.9802 (17), 11.5607 (18), 15.536 (2)
V (Å³)	1972.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.49 × 0.45 × 0.38

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.852, 0.882
No. of measured, independent and observed [I > 2σ(I)] reflections	10332, 3647, 3266
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.093, 1.03
No. of reflections	3647
No. of parameters	231
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20
Absolute structure	Flack (1983), 1556 Friedel pairs
Absolute structure parameter	0.06 (6)

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl2ⁱ	0.848 (19)	2.913 (13)	3.7023 (18)	156 (2)
O1—H1A···N1	0.82	1.93	2.642 (2)	144

Symmetry code: (i) −x+1/2, −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

Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cimarelli, C., Palmieri, G. & &Volpini, E. (2002). Tetrahedron Asymmetry, 13, 2011–2018. Web of Science CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Joshi, S. N. & Malhotra, S. V. (2003). Tetrahedron Asymmetry, 14, 1763–1766. Web of Science CrossRef CAS Google Scholar
Li, Y., He, B., Qin, B., Feng, X. & Zhang, G. (2004). J. Org. Chem. 69, 7910–7913. CrossRef PubMed CAS Google Scholar
Puigjaner, C., Vidal-Ferran, A., Moyano, A., Pericas, M. A., Rieras, M. A. & Riera, A. (1999). J. Org. Chem. 64, 7902–7911. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Watts, C. C., Thoniyot, P., Hirayama, L. C., Romano, T. & Singaram, B. (2005). Tetrahedron Asymmetry, 16, 1829–1835. Web of Science CrossRef CAS Google Scholar
Yang, X.-F., Zhang, G.-Y., Zhang, Y., Zhao, J.-Y. & Wang, X.-B. (2005). Acta Cryst. C61, o262–o264. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

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