4-Chloro-2-((1R)-1-{[(R)-(2-chlorophen-yl)(cyclo-pent-yl)meth-yl]amino}prop-yl)phenol.

In the title compound, C(21)H(25)Cl(2)NO, the dihedral angle between the two benzene rings is 33.18 (11)°. The five-membered ring adopts an envelope conformation. There is an intra-molecular O-H⋯N hydrogen bond. In the crystal, mol-ecules 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 = 378.32

Orthorhombic,

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 (; 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[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.093

S = 1.03

3647 reflections

231 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1556 Friedel pairs

Flack parameter: 0.06 (6)

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.

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

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

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

C21H25Cl2NO	F(000) = 800
Mr = 378.32	Dx = 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

Bruker SMART APEX CCD area-detector diffractometer	3647 independent reflections
Radiation source: fine-focus sealed tube	3266 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→13
Tmin = 0.852, Tmax = 0.882	k = −13→13
10332 measured reflections	l = −18→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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0504P)2 + 0.2043P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3647 reflections	Δρmax = 0.17 e Å−3
231 parameters	Δρmin = −0.20 e Å−3
1 restraint	Absolute structure: Flack (1983), 1556 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.06 (6)

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	0.4025 (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*

	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)

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)

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

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) .