2,4-Dichloro-6-((1R)-1-{[(R)-(2-chloro-phen-yl)(cyclo-pent-yl)meth-yl]amino}eth-yl)phenol.

In the title compound, C(20)H(22)Cl(3)NO, the five-membered ring adopts an envelope conformation, and the two benzene rings are oriented at a dihedral angle of 40.44 (9)°. Intra-molecular O-H⋯N and N-H⋯Cl hydrogen bonding is present. In the crystal, the mol-ecules are linked via weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C20H22Cl3NO

M = 398.74

Orthorhombic,

a = 8.4132 (7) Å

b = 13.6767 (10) Å

c = 17.0018 (14) Å

V = 1956.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 298 K

0.21 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.907, T max = 0.945

10361 measured reflections

3453 independent reflections

3005 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.04

3453 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1464 Friedel pairs

Flack parameter: 0.00 (7)

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809041403/xu2619sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041403/xu2619Isup2.hkl

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

C20H22Cl3NO	F(000) = 832
Mr = 398.74	Dx = 1.354 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4018 reflections
a = 8.4132 (7) Å	θ = 2.4–23.8°
b = 13.6767 (10) Å	µ = 0.48 mm−1
c = 17.0018 (14) Å	T = 298 K
V = 1956.3 (3) Å3	Plate, colorless
Z = 4	0.21 × 0.16 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	3453 independent reflections
Radiation source: fine-focus sealed tube	3005 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.907, Tmax = 0.945	k = −16→13
10361 measured reflections	l = −20→19

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0479P)2 + 0.4088P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3453 reflections	Δρmax = 0.20 e Å−3
227 parameters	Δρmin = −0.18 e Å−3
0 restraints	Absolute structure: Flack (1983), 1464 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (7)

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
Cl1	0.74492 (12)	0.20053 (6)	0.65026 (5)	0.0892 (3)
Cl2	0.77477 (11)	0.32755 (7)	0.35243 (5)	0.0818 (3)
Cl3	0.17174 (12)	0.73428 (6)	0.60165 (5)	0.0812 (3)
N1	0.4064 (2)	0.58218 (15)	0.51047 (11)	0.0438 (5)
H1N	0.3999	0.6424	0.5201	0.053*
O1	0.6034 (2)	0.49741 (14)	0.41237 (10)	0.0568 (5)
H1A	0.5277	0.5427	0.4341	0.068*
C1	0.6303 (3)	0.42963 (19)	0.46839 (14)	0.0444 (6)
C2	0.5780 (3)	0.44142 (18)	0.54534 (14)	0.0421 (5)
C3	0.6114 (3)	0.36909 (19)	0.60025 (16)	0.0498 (6)
H3	0.5742	0.3755	0.6515	0.060*
C4	0.6985 (3)	0.28820 (19)	0.57958 (18)	0.0568 (7)
C5	0.7529 (4)	0.2752 (2)	0.50434 (17)	0.0603 (7)
H5	0.8136	0.2208	0.4910	0.072*
C6	0.7148 (3)	0.3454 (2)	0.44879 (15)	0.0529 (6)
C7	0.5002 (3)	0.53592 (18)	0.57377 (14)	0.0464 (6)
H7	0.4300	0.5211	0.6182	0.056*
C8	0.6279 (4)	0.6086 (2)	0.6006 (2)	0.0712 (9)
H8A	0.7007	0.6206	0.5582	0.107*
H8B	0.6847	0.5818	0.6446	0.107*
H8C	0.5784	0.6689	0.6159	0.107*
C9	0.2437 (3)	0.54384 (17)	0.49936 (12)	0.0413 (5)
H9	0.2565	0.4764	0.4809	0.050*
C10	0.1458 (3)	0.53736 (19)	0.57434 (14)	0.0462 (6)
C11	0.1105 (3)	0.6155 (2)	0.62414 (15)	0.0551 (7)
C12	0.0257 (3)	0.6038 (3)	0.69294 (16)	0.0657 (9)
H12	0.0036	0.6578	0.7243	0.079*
C13	−0.0256 (4)	0.5139 (3)	0.71500 (17)	0.0722 (9)
H13	−0.0807	0.5061	0.7620	0.087*
C14	0.0042 (4)	0.4338 (3)	0.66735 (19)	0.0717 (9)
H14	−0.0323	0.3722	0.6821	0.086*
C15	0.0871 (3)	0.4449 (2)	0.59875 (16)	0.0555 (7)
H15	0.1055	0.3905	0.5673	0.067*
C16	0.1623 (3)	0.5990 (2)	0.43215 (14)	0.0480 (6)
H16	0.1482	0.6675	0.4478	0.058*
C17	−0.0009 (4)	0.5558 (3)	0.41129 (17)	0.0771 (10)
H17A	−0.0032	0.4861	0.4214	0.092*
H17B	−0.0843	0.5870	0.4417	0.092*
C18	−0.0216 (4)	0.5764 (4)	0.32453 (19)	0.1024 (14)
H18A	−0.0591	0.5182	0.2978	0.123*
H18B	−0.0995	0.6279	0.3170	0.123*
C19	0.1269 (4)	0.6057 (4)	0.29287 (18)	0.1004 (15)
H19A	0.1208	0.6730	0.2752	0.121*
H19B	0.1533	0.5650	0.2480	0.121*
C20	0.2520 (3)	0.5960 (2)	0.35444 (14)	0.0607 (7)
H20A	0.3275	0.6494	0.3511	0.073*
H20B	0.3088	0.5346	0.3487	0.073*

	U11	U22	U33	U12	U13	U23
Cl1	0.1119 (7)	0.0569 (4)	0.0988 (6)	0.0057 (5)	−0.0350 (6)	0.0237 (4)
Cl2	0.0826 (6)	0.0970 (6)	0.0659 (5)	0.0243 (5)	0.0076 (4)	−0.0202 (4)
Cl3	0.0997 (6)	0.0587 (4)	0.0852 (5)	0.0023 (4)	0.0080 (5)	−0.0205 (4)
N1	0.0408 (10)	0.0424 (11)	0.0481 (11)	0.0033 (9)	−0.0060 (9)	0.0035 (9)
O1	0.0513 (10)	0.0707 (12)	0.0484 (10)	0.0118 (9)	0.0076 (8)	0.0129 (9)
C1	0.0368 (12)	0.0505 (14)	0.0458 (13)	0.0015 (11)	−0.0041 (10)	0.0016 (11)
C2	0.0354 (12)	0.0429 (13)	0.0480 (14)	−0.0021 (11)	−0.0048 (10)	0.0026 (11)
C3	0.0511 (14)	0.0501 (14)	0.0483 (14)	−0.0045 (12)	−0.0077 (12)	0.0047 (11)
C4	0.0573 (16)	0.0423 (15)	0.0709 (19)	0.0000 (12)	−0.0216 (14)	0.0066 (13)
C5	0.0590 (16)	0.0455 (15)	0.077 (2)	0.0077 (14)	−0.0160 (14)	−0.0090 (13)
C6	0.0455 (14)	0.0606 (16)	0.0527 (15)	0.0038 (13)	−0.0047 (12)	−0.0112 (12)
C7	0.0444 (12)	0.0514 (15)	0.0433 (13)	0.0056 (12)	−0.0034 (11)	0.0009 (11)
C8	0.0663 (19)	0.0613 (18)	0.086 (2)	0.0053 (15)	−0.0273 (17)	−0.0162 (16)
C9	0.0398 (12)	0.0444 (12)	0.0397 (12)	0.0040 (11)	0.0000 (10)	−0.0036 (9)
C10	0.0376 (12)	0.0568 (15)	0.0442 (13)	0.0039 (11)	−0.0060 (10)	0.0000 (11)
C11	0.0459 (14)	0.0722 (18)	0.0473 (14)	0.0037 (13)	−0.0065 (12)	−0.0100 (13)
C12	0.0479 (16)	0.107 (3)	0.0423 (15)	0.0089 (17)	−0.0037 (13)	−0.0125 (16)
C13	0.0513 (17)	0.121 (3)	0.0446 (16)	0.0014 (19)	−0.0023 (13)	0.0113 (19)
C14	0.0548 (16)	0.091 (2)	0.069 (2)	−0.0134 (18)	−0.0066 (16)	0.0246 (18)
C15	0.0467 (14)	0.0685 (18)	0.0512 (15)	−0.0014 (13)	−0.0035 (12)	−0.0006 (13)
C16	0.0487 (14)	0.0514 (15)	0.0438 (13)	0.0091 (12)	−0.0049 (11)	−0.0032 (11)
C17	0.0420 (14)	0.137 (3)	0.0519 (17)	0.0015 (19)	−0.0033 (13)	0.0090 (18)
C18	0.062 (2)	0.189 (4)	0.0560 (19)	−0.016 (3)	−0.0167 (16)	0.025 (2)
C19	0.064 (2)	0.192 (5)	0.0453 (17)	0.001 (3)	−0.0046 (15)	0.014 (2)
C20	0.0469 (15)	0.088 (2)	0.0476 (14)	−0.0023 (14)	−0.0027 (13)	0.0102 (14)

Cl1—C4	1.742 (3)	C10—C11	1.395 (4)
Cl2—C6	1.731 (3)	C10—C15	1.419 (4)
Cl3—C11	1.747 (3)	C11—C12	1.379 (4)
N1—C7	1.477 (3)	C12—C13	1.356 (5)
N1—C9	1.478 (3)	C12—H12	0.9300
N1—H1N	0.8410	C13—C14	1.386 (5)
O1—C1	1.348 (3)	C13—H13	0.9300
O1—H1A	0.9621	C14—C15	1.368 (4)
C1—C2	1.390 (4)	C14—H14	0.9300
C1—C6	1.395 (4)	C15—H15	0.9300
C2—C3	1.389 (3)	C16—C20	1.522 (3)
C2—C7	1.527 (3)	C16—C17	1.536 (4)
C3—C4	1.373 (4)	C16—H16	0.9800
C3—H3	0.9300	C17—C18	1.512 (4)
C4—C5	1.370 (4)	C17—H17A	0.9700
C5—C6	1.384 (4)	C17—H17B	0.9700
C5—H5	0.9300	C18—C19	1.417 (5)
C7—C8	1.533 (4)	C18—H18A	0.9700
C7—H7	0.9800	C18—H18B	0.9700
C8—H8A	0.9600	C19—C20	1.491 (4)
C8—H8B	0.9600	C19—H19A	0.9700
C8—H8C	0.9600	C19—H19B	0.9700
C9—C10	1.521 (3)	C20—H20A	0.9700
C9—C16	1.531 (3)	C20—H20B	0.9700
C9—H9	0.9800
C7—N1—C9	115.86 (19)	C12—C11—Cl3	116.5 (2)
C7—N1—H1N	108.2	C10—C11—Cl3	121.1 (2)
C9—N1—H1N	108.2	C13—C12—C11	120.2 (3)
C1—O1—H1A	106.4	C13—C12—H12	119.9
O1—C1—C2	122.1 (2)	C11—C12—H12	119.9
O1—C1—C6	119.0 (2)	C12—C13—C14	119.9 (3)
C2—C1—C6	118.8 (2)	C12—C13—H13	120.1
C3—C2—C1	119.1 (2)	C14—C13—H13	120.1
C3—C2—C7	118.5 (2)	C15—C14—C13	120.1 (3)
C1—C2—C7	122.1 (2)	C15—C14—H14	119.9
C4—C3—C2	120.6 (3)	C13—C14—H14	119.9
C4—C3—H3	119.7	C14—C15—C10	121.8 (3)
C2—C3—H3	119.7	C14—C15—H15	119.1
C5—C4—C3	121.5 (2)	C10—C15—H15	119.1
C5—C4—Cl1	118.7 (2)	C20—C16—C9	114.3 (2)
C3—C4—Cl1	119.8 (2)	C20—C16—C17	103.4 (2)
C4—C5—C6	118.0 (2)	C9—C16—C17	112.5 (2)
C4—C5—H5	121.0	C20—C16—H16	108.8
C6—C5—H5	121.0	C9—C16—H16	108.8
C5—C6—C1	121.9 (2)	C17—C16—H16	108.8
C5—C6—Cl2	118.7 (2)	C18—C17—C16	104.8 (3)
C1—C6—Cl2	119.4 (2)	C18—C17—H17A	110.8
N1—C7—C2	111.16 (19)	C16—C17—H17A	110.8
N1—C7—C8	108.3 (2)	C18—C17—H17B	110.8
C2—C7—C8	110.0 (2)	C16—C17—H17B	110.8
N1—C7—H7	109.1	H17A—C17—H17B	108.9
C2—C7—H7	109.1	C19—C18—C17	108.8 (3)
C8—C7—H7	109.1	C19—C18—H18A	109.9
C7—C8—H8A	109.5	C17—C18—H18A	109.9
C7—C8—H8B	109.5	C19—C18—H18B	109.9
H8A—C8—H8B	109.5	C17—C18—H18B	109.9
C7—C8—H8C	109.5	H18A—C18—H18B	108.3
H8A—C8—H8C	109.5	C18—C19—C20	109.3 (3)
H8B—C8—H8C	109.5	C18—C19—H19A	109.8
N1—C9—C10	114.55 (18)	C20—C19—H19A	109.8
N1—C9—C16	109.57 (19)	C18—C19—H19B	109.8
C10—C9—C16	114.31 (19)	C20—C19—H19B	109.8
N1—C9—H9	105.9	H19A—C19—H19B	108.3
C10—C9—H9	105.9	C19—C20—C16	104.9 (2)
C16—C9—H9	105.9	C19—C20—H20A	110.8
C11—C10—C15	115.5 (2)	C16—C20—H20A	110.8
C11—C10—C9	125.4 (2)	C19—C20—H20B	110.8
C15—C10—C9	119.1 (2)	C16—C20—H20B	110.8
C12—C11—C10	122.4 (3)	H20A—C20—H20B	108.8
O1—C1—C2—C3	−179.4 (2)	C16—C9—C10—C11	−69.6 (3)
C6—C1—C2—C3	0.0 (4)	N1—C9—C10—C15	−120.1 (2)
O1—C1—C2—C7	−5.9 (4)	C16—C9—C10—C15	112.3 (3)
C6—C1—C2—C7	173.5 (2)	C15—C10—C11—C12	0.6 (4)
C1—C2—C3—C4	1.8 (4)	C9—C10—C11—C12	−177.5 (2)
C7—C2—C3—C4	−171.9 (2)	C15—C10—C11—Cl3	−179.05 (19)
C2—C3—C4—C5	−1.2 (4)	C9—C10—C11—Cl3	2.8 (3)
C2—C3—C4—Cl1	177.7 (2)	C10—C11—C12—C13	0.7 (4)
C3—C4—C5—C6	−1.2 (4)	Cl3—C11—C12—C13	−179.6 (2)
Cl1—C4—C5—C6	179.9 (2)	C11—C12—C13—C14	−1.5 (4)
C4—C5—C6—C1	3.1 (4)	C12—C13—C14—C15	0.9 (4)
C4—C5—C6—Cl2	−177.1 (2)	C13—C14—C15—C10	0.4 (4)
O1—C1—C6—C5	176.9 (2)	C11—C10—C15—C14	−1.2 (4)
C2—C1—C6—C5	−2.4 (4)	C9—C10—C15—C14	177.1 (2)
O1—C1—C6—Cl2	−2.9 (3)	N1—C9—C16—C20	56.3 (3)
C2—C1—C6—Cl2	177.76 (19)	C10—C9—C16—C20	−173.6 (2)
C9—N1—C7—C2	83.1 (2)	N1—C9—C16—C17	173.9 (2)
C9—N1—C7—C8	−155.9 (2)	C10—C9—C16—C17	−56.0 (3)
C3—C2—C7—N1	−153.0 (2)	C20—C16—C17—C18	−26.1 (4)
C1—C2—C7—N1	33.4 (3)	C9—C16—C17—C18	−150.0 (3)
C3—C2—C7—C8	87.0 (3)	C16—C17—C18—C19	13.3 (5)
C1—C2—C7—C8	−86.5 (3)	C17—C18—C19—C20	5.6 (6)
C7—N1—C9—C10	49.9 (3)	C18—C19—C20—C16	−22.4 (5)
C7—N1—C9—C16	179.88 (18)	C9—C16—C20—C19	152.1 (3)
N1—C9—C10—C11	58.0 (3)	C17—C16—C20—C19	29.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.96	1.74	2.622 (3)	151
N1—H1N···Cl3	0.84	2.68	3.260 (2)	127
C13—H13···O1i	0.93	2.56	3.422 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.96	1.74	2.622 (3)	151
N1—H1N⋯Cl3	0.84	2.68	3.260 (2)	127
C13—H13⋯O1i	0.93	2.56	3.422 (3)	154

Symmetry code: (i) .