N-[(R)-(2-Chloro-phen-yl)(cyclo-pent-yl)meth-yl]-N-[(R)-(2-hydr-oxy-5-methyl-phen-yl)(phen-yl)meth-yl]acetamide.

In the title compound, C(28)H(30)ClNO(2), the cyclo-pentane ring adopts an envelope conformation. In the crystal structure, mol-ecules are linked by inter-molecular O-H⋯O hydrogen bonds, forming chains running along the a axis.

Related literature

For general background to amides, see: Calligaris et al. (1972 ▶); Ali et al. (2002 ▶); Cukurovali et al. (2002 ▶); Sriram et al. (2006 ▶); Kargar et al. (2009 ▶); Takenaka et al. (2002 ▶); Varlamov et al. (2003 ▶); Zhang et al. (2003 ▶). For the synthesis, see: Yang et al. (2005 ▶).

Experimental

Crystal data

C28H30ClNO2

M = 447.98

Orthorhombic,

a = 8.8038 (8) Å

b = 11.3417 (10) Å

c = 25.485 (2) Å

V = 2544.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 298 K

0.24 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.960, T max = 0.980

13334 measured reflections

4452 independent reflections

2845 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.186

S = 1.05

4452 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.37 e Å−3

Absolute structure: Flack (1983 ▶), 1871 Friedel pairs

Flack parameter: 0.04 (16)

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/S1600536809044808/xu2646sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044808/xu2646Isup2.hkl

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

C28H30ClNO2	F(000) = 952
Mr = 447.98	Dx = 1.169 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2267 reflections
a = 8.8038 (8) Å	θ = 2.5–19.1°
b = 11.3417 (10) Å	µ = 0.17 mm−1
c = 25.485 (2) Å	T = 298 K
V = 2544.7 (4) Å3	Block, colourless
Z = 4	0.24 × 0.16 × 0.12 mm

Bruker SMART CCD area-detector diffractometer	4452 independent reflections
Radiation source: fine-focus sealed tube	2845 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→10
Tmin = 0.960, Tmax = 0.980	k = −12→13
13334 measured reflections	l = −26→30

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)] = 0.060	H-atom parameters constrained
wR(F2) = 0.186	w = 1/[σ2(Fo2) + (0.1097P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
4452 reflections	Δρmax = 0.33 e Å−3
290 parameters	Δρmin = −0.36 e Å−3
0 restraints	Absolute structure: Flack (1983), 1871 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (16)

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	0.8441 (4)	1.17857 (19)	0.06402 (7)	0.1811 (11)
O1	0.2924 (3)	0.8872 (3)	0.12767 (13)	0.0864 (9)
H1	0.2020	0.9041	0.1256	0.130*
O2	1.0028 (3)	0.9464 (3)	0.13070 (14)	0.0927 (10)
N1	0.7501 (3)	0.9350 (2)	0.13768 (11)	0.0520 (7)
C1	0.3627 (4)	0.9125 (3)	0.08087 (15)	0.0626 (9)
C2	0.5208 (3)	0.9060 (3)	0.08034 (14)	0.0536 (9)
C3	0.5941 (4)	0.9335 (3)	0.03418 (15)	0.0628 (10)
H3	0.6996	0.9297	0.0333	0.075*
C4	0.5179 (5)	0.9666 (4)	−0.01089 (15)	0.0746 (12)
C5	0.3620 (6)	0.9721 (4)	−0.00895 (17)	0.0834 (13)
H5	0.3081	0.9942	−0.0387	0.100*
C6	0.2852 (4)	0.9457 (4)	0.03610 (19)	0.0769 (12)
H6	0.1797	0.9501	0.0366	0.092*
C7	0.6058 (8)	0.9962 (6)	−0.06040 (18)	0.125 (2)
H7A	0.6982	0.9512	−0.0613	0.188*
H7B	0.6297	1.0788	−0.0607	0.188*
H7C	0.5453	0.9773	−0.0906	0.188*
C8	0.6007 (3)	0.8750 (3)	0.13155 (14)	0.0512 (8)
H8	0.5365	0.9094	0.1590	0.061*
C9	0.6029 (4)	0.7431 (4)	0.14369 (18)	0.0672 (11)
C10	0.5359 (5)	0.6629 (4)	0.1108 (3)	0.0967 (16)
H10	0.4909	0.6891	0.0799	0.116*
C11	0.5336 (7)	0.5430 (5)	0.1227 (4)	0.127 (2)
H11	0.4850	0.4906	0.1003	0.152*
C12	0.6012 (8)	0.5029 (6)	0.1664 (4)	0.135 (3)
H12	0.6032	0.4224	0.1733	0.162*
C13	0.6684 (7)	0.5812 (6)	0.2016 (3)	0.121 (2)
H13	0.7133	0.5534	0.2322	0.146*
C14	0.6677 (5)	0.7034 (5)	0.1903 (2)	0.0923 (14)
H14	0.7102	0.7568	0.2139	0.111*
C15	0.8845 (4)	0.8931 (4)	0.12091 (16)	0.0655 (10)
C16	0.8935 (4)	0.7808 (4)	0.0899 (2)	0.0860 (14)
H16A	0.9720	0.7875	0.0639	0.129*
H16B	0.7979	0.7666	0.0729	0.129*
H16C	0.9162	0.7163	0.1130	0.129*
C17	0.7476 (4)	1.0531 (3)	0.16311 (13)	0.0566 (8)
H17	0.8468	1.0892	0.1564	0.068*
C18	0.6322 (6)	1.1299 (4)	0.13737 (15)	0.0781 (12)
C19	0.6669 (10)	1.1861 (4)	0.0904 (2)	0.127 (2)
C20	0.5516 (12)	1.2498 (6)	0.0618 (3)	0.149 (2)
H20	0.5730	1.2880	0.0304	0.179*
C21	0.4125 (12)	1.2510 (7)	0.0828 (4)	0.156 (3)
H21	0.3363	1.2890	0.0640	0.187*
C22	0.3740 (9)	1.2019 (6)	0.1287 (4)	0.152 (3)
H22	0.2755	1.2079	0.1416	0.182*
C23	0.4846 (6)	1.1424 (5)	0.1564 (3)	0.1053 (17)
H23	0.4599	1.1095	0.1887	0.126*
C24	0.7295 (5)	1.0460 (4)	0.22294 (17)	0.0842 (12)
H24	0.6317	1.0095	0.2316	0.101*
C25	0.8582 (7)	0.9781 (6)	0.24986 (19)	0.1152 (16)
H25A	0.8233	0.8997	0.2591	0.138*
H25B	0.9432	0.9701	0.2259	0.138*
C26	0.9037 (9)	1.0362 (7)	0.2938 (3)	0.150 (2)
H26A	1.0137	1.0356	0.2958	0.180*
H26B	0.8646	0.9959	0.3246	0.180*
C27	0.8506 (8)	1.1554 (7)	0.2936 (2)	0.1364 (19)
H27A	0.9355	1.2091	0.2893	0.164*
H27B	0.8008	1.1733	0.3266	0.164*
C28	0.7391 (7)	1.1699 (5)	0.24837 (19)	0.1022 (14)
H28A	0.7759	1.2276	0.2233	0.123*
H28B	0.6404	1.1948	0.2611	0.123*

	U11	U22	U33	U12	U13	U23
Cl1	0.303 (3)	0.1376 (15)	0.1031 (11)	−0.0737 (18)	0.0624 (16)	0.0110 (10)
O1	0.0368 (13)	0.119 (3)	0.103 (2)	0.0043 (13)	0.0143 (14)	0.021 (2)
O2	0.0339 (12)	0.114 (2)	0.130 (3)	−0.0049 (14)	0.0073 (15)	−0.034 (2)
N1	0.0335 (12)	0.0595 (17)	0.0629 (16)	0.0023 (12)	−0.0005 (13)	−0.0064 (13)
C1	0.0391 (18)	0.074 (2)	0.075 (2)	−0.0015 (17)	0.0032 (18)	0.0019 (19)
C2	0.0383 (17)	0.056 (2)	0.067 (2)	−0.0048 (14)	0.0028 (15)	−0.0060 (16)
C3	0.053 (2)	0.071 (2)	0.065 (2)	−0.0095 (17)	0.0037 (18)	−0.0108 (18)
C4	0.080 (3)	0.084 (3)	0.060 (2)	−0.031 (2)	0.003 (2)	−0.009 (2)
C5	0.091 (3)	0.087 (3)	0.071 (3)	−0.012 (3)	−0.024 (3)	−0.003 (2)
C6	0.049 (2)	0.088 (3)	0.093 (3)	−0.0030 (19)	−0.020 (2)	−0.005 (2)
C7	0.149 (5)	0.164 (6)	0.063 (3)	−0.065 (4)	0.003 (3)	0.010 (3)
C8	0.0328 (15)	0.057 (2)	0.064 (2)	0.0000 (13)	0.0049 (15)	0.0002 (16)
C9	0.0408 (17)	0.060 (2)	0.101 (3)	−0.0027 (16)	0.0080 (19)	0.008 (2)
C10	0.073 (3)	0.066 (3)	0.151 (5)	−0.008 (2)	0.007 (3)	−0.002 (3)
C11	0.109 (4)	0.060 (3)	0.212 (7)	−0.004 (3)	0.001 (5)	−0.004 (4)
C12	0.109 (5)	0.074 (4)	0.221 (8)	0.019 (4)	0.044 (5)	0.028 (5)
C13	0.103 (4)	0.103 (5)	0.157 (6)	0.023 (4)	0.021 (4)	0.058 (5)
C14	0.075 (3)	0.093 (4)	0.109 (3)	0.009 (2)	0.010 (3)	0.030 (3)
C15	0.0380 (19)	0.079 (3)	0.080 (2)	0.0035 (18)	0.0028 (17)	−0.008 (2)
C16	0.049 (2)	0.093 (3)	0.116 (3)	0.013 (2)	0.022 (2)	−0.024 (3)
C17	0.0516 (18)	0.060 (2)	0.058 (2)	0.0015 (18)	−0.0008 (17)	−0.0073 (16)
C18	0.113 (3)	0.055 (2)	0.066 (2)	0.020 (2)	−0.028 (2)	−0.0157 (19)
C19	0.227 (6)	0.063 (3)	0.091 (3)	0.020 (4)	−0.053 (4)	−0.011 (3)
C20	0.237 (7)	0.098 (4)	0.111 (4)	0.032 (5)	−0.063 (5)	−0.011 (3)
C21	0.215 (7)	0.099 (4)	0.153 (6)	0.060 (5)	−0.088 (6)	−0.031 (4)
C22	0.152 (5)	0.115 (5)	0.187 (6)	0.066 (4)	−0.051 (5)	−0.060 (4)
C23	0.085 (3)	0.088 (3)	0.143 (4)	0.044 (3)	−0.048 (3)	−0.046 (3)
C24	0.082 (3)	0.106 (3)	0.065 (2)	0.003 (2)	−0.019 (2)	−0.016 (2)
C25	0.129 (4)	0.132 (4)	0.084 (3)	0.010 (3)	−0.048 (3)	−0.006 (3)
C26	0.147 (4)	0.177 (5)	0.126 (4)	0.022 (4)	−0.053 (3)	−0.028 (4)
C27	0.133 (4)	0.156 (4)	0.120 (3)	0.000 (4)	−0.044 (3)	−0.042 (3)
C28	0.102 (3)	0.126 (3)	0.078 (3)	0.010 (3)	−0.015 (3)	−0.037 (3)

Cl1—C19	1.701 (9)	C14—H14	0.9300
O1—C1	1.374 (5)	C15—C16	1.501 (6)
O1—H1	0.8200	C16—H16A	0.9600
O2—C15	1.230 (4)	C16—H16B	0.9600
N1—C15	1.345 (4)	C16—H16C	0.9600
N1—C17	1.488 (4)	C17—C18	1.490 (5)
N1—C8	1.489 (4)	C17—C24	1.535 (6)
C1—C6	1.382 (6)	C17—H17	0.9800
C1—C2	1.394 (5)	C18—C19	1.391 (8)
C2—C3	1.377 (5)	C18—C23	1.394 (7)
C2—C8	1.524 (5)	C19—C20	1.443 (9)
C3—C4	1.382 (6)	C20—C21	1.337 (12)
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.374 (7)	C21—C22	1.340 (11)
C4—C7	1.518 (6)	C21—H21	0.9300
C5—C6	1.366 (6)	C22—C23	1.379 (9)
C5—H5	0.9300	C22—H22	0.9300
C6—H6	0.9300	C23—H23	0.9300
C7—H7A	0.9600	C24—C25	1.532 (7)
C7—H7B	0.9600	C24—C28	1.550 (7)
C7—H7C	0.9600	C24—H24	0.9800
C8—C9	1.528 (5)	C25—C26	1.361 (8)
C8—H8	0.9800	C25—H25A	0.9700
C9—C10	1.370 (7)	C25—H25B	0.9700
C9—C14	1.394 (6)	C26—C27	1.430 (10)
C10—C11	1.393 (8)	C26—H26A	0.9700
C10—H10	0.9300	C26—H26B	0.9700
C11—C12	1.343 (11)	C27—C28	1.523 (8)
C11—H11	0.9300	C27—H27A	0.9700
C12—C13	1.394 (10)	C27—H27B	0.9700
C12—H12	0.9300	C28—H28A	0.9700
C13—C14	1.415 (8)	C28—H28B	0.9700
C13—H13	0.9300
C1—O1—H1	109.5	C15—C16—H16C	109.5
C15—N1—C17	118.0 (3)	H16A—C16—H16C	109.5
C15—N1—C8	125.6 (3)	H16B—C16—H16C	109.5
C17—N1—C8	116.3 (2)	N1—C17—C18	110.2 (3)
O1—C1—C6	123.5 (3)	N1—C17—C24	112.8 (3)
O1—C1—C2	116.6 (3)	C18—C17—C24	113.4 (3)
C6—C1—C2	119.9 (4)	N1—C17—H17	106.7
C3—C2—C1	117.7 (3)	C18—C17—H17	106.7
C3—C2—C8	124.6 (3)	C24—C17—H17	106.7
C1—C2—C8	117.7 (3)	C19—C18—C23	117.2 (5)
C2—C3—C4	122.9 (3)	C19—C18—C17	119.8 (5)
C2—C3—H3	118.5	C23—C18—C17	122.8 (4)
C4—C3—H3	118.5	C18—C19—C20	120.6 (8)
C5—C4—C3	117.9 (4)	C18—C19—Cl1	121.2 (5)
C5—C4—C7	122.0 (4)	C20—C19—Cl1	118.1 (6)
C3—C4—C7	120.2 (4)	C21—C20—C19	116.6 (8)
C6—C5—C4	121.0 (4)	C21—C20—H20	121.7
C6—C5—H5	119.5	C19—C20—H20	121.7
C4—C5—H5	119.5	C20—C21—C22	125.2 (8)
C5—C6—C1	120.6 (4)	C20—C21—H21	117.4
C5—C6—H6	119.7	C22—C21—H21	117.4
C1—C6—H6	119.7	C21—C22—C23	118.2 (8)
C4—C7—H7A	109.5	C21—C22—H22	120.9
C4—C7—H7B	109.5	C23—C22—H22	120.9
H7A—C7—H7B	109.5	C22—C23—C18	122.0 (7)
C4—C7—H7C	109.5	C22—C23—H23	119.0
H7A—C7—H7C	109.5	C18—C23—H23	119.0
H7B—C7—H7C	109.5	C25—C24—C17	113.2 (4)
N1—C8—C2	113.1 (3)	C25—C24—C28	103.2 (4)
N1—C8—C9	114.5 (3)	C17—C24—C28	111.2 (4)
C2—C8—C9	113.9 (3)	C25—C24—H24	109.7
N1—C8—H8	104.6	C17—C24—H24	109.7
C2—C8—H8	104.6	C28—C24—H24	109.7
C9—C8—H8	104.6	C26—C25—C24	110.1 (5)
C10—C9—C14	118.9 (4)	C26—C25—H25A	109.6
C10—C9—C8	121.4 (4)	C24—C25—H25A	109.6
C14—C9—C8	119.6 (4)	C26—C25—H25B	109.6
C9—C10—C11	121.4 (6)	C24—C25—H25B	109.6
C9—C10—H10	119.3	H25A—C25—H25B	108.2
C11—C10—H10	119.3	C25—C26—C27	111.0 (6)
C12—C11—C10	120.3 (7)	C25—C26—H26A	109.4
C12—C11—H11	119.8	C27—C26—H26A	109.4
C10—C11—H11	119.8	C25—C26—H26B	109.4
C11—C12—C13	120.4 (6)	C27—C26—H26B	109.4
C11—C12—H12	119.8	H26A—C26—H26B	108.0
C13—C12—H12	119.8	C26—C27—C28	108.4 (5)
C12—C13—C14	119.5 (6)	C26—C27—H27A	110.0
C12—C13—H13	120.3	C28—C27—H27A	110.0
C14—C13—H13	120.3	C26—C27—H27B	110.0
C9—C14—C13	119.4 (6)	C28—C27—H27B	110.0
C9—C14—H14	120.3	H27A—C27—H27B	108.4
C13—C14—H14	120.3	C27—C28—C24	104.7 (4)
O2—C15—N1	120.4 (3)	C27—C28—H28A	110.8
O2—C15—C16	118.6 (3)	C24—C28—H28A	110.8
N1—C15—C16	120.9 (3)	C27—C28—H28B	110.8
C15—C16—H16A	109.5	C24—C28—H28B	110.8
C15—C16—H16B	109.5	H28A—C28—H28B	108.9
H16A—C16—H16B	109.5
O1—C1—C2—C3	−178.6 (3)	C8—N1—C15—O2	−175.7 (4)
C6—C1—C2—C3	−0.1 (5)	C17—N1—C15—C16	−173.5 (4)
O1—C1—C2—C8	−1.6 (5)	C8—N1—C15—C16	4.4 (6)
C6—C1—C2—C8	176.9 (3)	C15—N1—C17—C18	127.5 (4)
C1—C2—C3—C4	−0.1 (6)	C8—N1—C17—C18	−50.6 (4)
C8—C2—C3—C4	−176.9 (3)	C15—N1—C17—C24	−104.7 (4)
C2—C3—C4—C5	0.1 (6)	C8—N1—C17—C24	77.2 (4)
C2—C3—C4—C7	179.8 (4)	N1—C17—C18—C19	−80.3 (5)
C3—C4—C5—C6	0.0 (7)	C24—C17—C18—C19	152.2 (4)
C7—C4—C5—C6	−179.7 (5)	N1—C17—C18—C23	95.1 (4)
C4—C5—C6—C1	−0.1 (7)	C24—C17—C18—C23	−32.4 (5)
O1—C1—C6—C5	178.6 (4)	C23—C18—C19—C20	−2.8 (7)
C2—C1—C6—C5	0.2 (6)	C17—C18—C19—C20	172.9 (5)
C15—N1—C8—C2	−89.0 (4)	C23—C18—C19—Cl1	179.0 (4)
C17—N1—C8—C2	88.9 (3)	C17—C18—C19—Cl1	−5.3 (6)
C15—N1—C8—C9	43.7 (5)	C18—C19—C20—C21	−0.2 (9)
C17—N1—C8—C9	−138.3 (3)	Cl1—C19—C20—C21	178.1 (6)
C3—C2—C8—N1	30.9 (5)	C19—C20—C21—C22	2.6 (12)
C1—C2—C8—N1	−145.9 (3)	C20—C21—C22—C23	−1.8 (12)
C3—C2—C8—C9	−102.2 (4)	C21—C22—C23—C18	−1.5 (9)
C1—C2—C8—C9	81.0 (4)	C19—C18—C23—C22	3.7 (7)
N1—C8—C9—C10	−133.2 (4)	C17—C18—C23—C22	−171.8 (5)
C2—C8—C9—C10	−0.9 (5)	N1—C17—C24—C25	60.2 (5)
N1—C8—C9—C14	49.9 (5)	C18—C17—C24—C25	−173.7 (4)
C2—C8—C9—C14	−177.7 (3)	N1—C17—C24—C28	175.9 (3)
C14—C9—C10—C11	−1.1 (7)	C18—C17—C24—C28	−58.1 (5)
C8—C9—C10—C11	−177.9 (4)	C17—C24—C25—C26	136.6 (6)
C9—C10—C11—C12	−1.7 (9)	C28—C24—C25—C26	16.2 (7)
C10—C11—C12—C13	2.9 (10)	C24—C25—C26—C27	−16.4 (10)
C11—C12—C13—C14	−1.4 (10)	C25—C26—C27—C28	9.3 (10)
C10—C9—C14—C13	2.6 (7)	C26—C27—C28—C24	1.3 (8)
C8—C9—C14—C13	179.5 (4)	C25—C24—C28—C27	−9.9 (6)
C12—C13—C14—C9	−1.4 (8)	C17—C24—C28—C27	−131.6 (5)
C17—N1—C15—O2	6.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.82	2.637 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.82	2.637 (3)	172

Symmetry code: (i) .