4-Chloro-2-((1R)-1-{[(R)-(2-chloro-phen-yl)(cyclo-pent-yl)meth-yl]amino}eth-yl)phenol.

The title compound, C(20)H(23)Cl(2)NO, was prepared by condensation of (R)-1-(2-chloro-phen-yl)-1-cyclo-pentyl-methanamine with 1-(5-chloro-2-hydroxy-phen-yl)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 intra-molecular O-H⋯N hydrogen bond which stabilizes the conformation of the mol-ecule. The mol-ecules are linked to each other through weak C-H⋯π inter-actions.

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 = 364.29

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.113

S = 1.02

3573 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 1629 Friedel pairs

Flack parameter: 0.03 (8)

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H23Cl2NO	F(000) = 768
Mr = 364.29	Dx = 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

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

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(Fo2) + (0.0486P)2 + 0.3378P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3573 reflections	Δρmax = 0.17 e Å−3
219 parameters	Δρmin = −0.22 e Å−3
0 restraints	Absolute structure: Flack (1983), 1629 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (8)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) . Cg is the centroid of the C15–C20 benzene ring