(2R,3R)-2-[(4-Chloro­phen­yl)hydroxy­meth­yl]cyclo­penta­none

Deng, D.; Liu, P.; Fu, W.; Ji, B.

doi:10.1107/S160053680804261X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Pages o164-o165

doi:10.1107/S160053680804261X

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(2R,3R)-2-[(4-Chlorophenyl)hydroxymethyl]cyclopentanone

Dongsheng Deng,^a Ping Liu,^b Weijun Fu ^a and Baoming Ji ^a ^*

^aCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Henan Institute of Science and Technology, Xinxiang, Henan 453003, People's Republic of China
^*Correspondence e-mail: lyhxxjbm@126.com

(Received 4 December 2008; accepted 15 December 2008; online 20 December 2008)

The title compound, C₁₂H₁₃ClO₂, was prepared by the direct asymmetric intermolecular aldol reaction of cyclopentanone and 4-chlorobenzaldehyde catalysed by L-tryptophan in water. The absolute molecular structure was determined to be a racemic twin with 91% (2R,3R) isomer and 9% of the (2S,3S) form. In the crystal structure, the molecules are connected into a one-dimensional chain along the a axis through the formation of intermolecular O—H⋯O hydrogen bonds. Further, non-conventional C—H⋯O and C—H⋯π contacts are observed in the structure, which consolidate the crystal packing.

Related literature

For the structure of 2-[hydroxy(4-nitrophenyl)methyl]-4-methylcyclohexanone, see: Li (2007 ). For a structure with C—H⋯O hydrogen bonds, see: Nangia (2002 ). For a database study of C—H⋯π interactions in the conformation of peptides, see: Umezawa et al. (1999 ). For direct intermolecular aldol reactions catalysed by acyclic amino acids, see: Córdova et al. (2006 ); Deng & Cai (2007 ). For asymmetric direct aldol reaction assisted by water and a proline-derived tetrazole catalyst, see: Torii et al. (2004 ). For the development of direct catalytic asymmetric aldol, Mannich, Michael and Diels–Alder reactions, see: Notz et al. (2004 ).

Experimental

Crystal data

C₁₂H₁₃ClO₂
M_r = 224.67
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.7401 (1) Å
b = 10.4549 (2) Å
c = 18.2135 (3) Å
V = 1093.03 (3) Å³
Z = 4
Cu Kα radiation
μ = 2.90 mm⁻¹
T = 150 (2) K
0.43 × 0.31 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.336, T_max = 0.484
3762 measured reflections
1936 independent reflections
1865 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.168
S = 1.14
1936 reflections
146 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.52 e Å⁻³
Absolute structure: Flack (1983 ), 572 Friedel pairs
Flack parameter: 0.09 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.92 (7)	1.89 (7)	2.793 (4)	165 (7)
C10—H10A⋯O2ⁱⁱ	0.99	2.53	3.328 (5)	138
C5—H5A⋯Cg2ⁱⁱⁱ	0.95	2.96	3.818 (4)	150
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iii) $[-x, y+{\script{3\over 2}}, -z+{\script{1\over 2}}]$ . Cg2 is the centroid of the C1–C5,C12 ring.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680804261X/si2143sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680804261X/si2143Isup2.hkl

checkCIF report

Comment top

The direct asymmetric aldol reaction is one of the most important C—C bond-forming reactions (Notz et al., 2004.). It is not surprising that a large number of catalysts and methods have been developed to achieve efficient adducts with high diastereo- and enantioselectivities (Córdova et al. 2006; Torii et al. 2004.). Our primary results demonstrating that acyclic amino acids could catalyze the direct stereoseletive aldol reaction in water micelles (Deng & Cai, 2007). In this contribution, as an extension to our previous studies, we report the synthesis and crystal structure of the title compound.

In the title compound (Fig. 1.), the bond lengths and angles are within ranges as reported by Li (2007). The structural analysis reveals that the absolute molecular structure was a (2R, 3R)- isomer. The most striking feature of the title compound is the interesting arrangement of the title molecules, which connect each other to form a one-dimension chain along the a axis by intermolecular O—H···O hydrogen bonds (Fig. 2). Furthermore, the weak non-conventional intermolecular C—H···π contact is observed, in which C5—H5A is donor and the chlorophenyl ring Cg2 (C1, C2, C3, C4, C12, C5) is π acceptor (Umezawa et al., 1999). This contact, with additional intermolecular C—H···O interactions (Nangia et al. 2002), further consolidate the crystal packing. Details of hydrogen bonds are given in Table 1.

Related literature top

For the structure of 2-[hydroxy(4-nitrophenyl)methyl]-4-methylcyclohexanone, see: Li (2007). For a structure with C—H···O hydrogen bonds, see: Nangia (2002). For a database study of C—H···π interactions in the conformation of peptides, see: Umezawa et al. (1999). For direct intermolecular aldol reactions catalysed by acyclic amino acids, see: Córdova et al. (2006); Deng & Cai (2007). For asymmetric direct aldol reaction assisted by water and a proline-derived tetrazole catalyst, see: Torii et al. (2004). For the development of direct catalytic asymmetric aldol, Mannich, Michael and Diels–Alder reactions, see: Notz et al. (2004). Cg2 is the centroid of the C1–C5,C12 ring.

Experimental top

4-chlorobenzaldehyde (71 mm g, 0.5 mmol) and cyclopentanone (0.5 ml) was added to a solution of L-tryptophan (30.6 mg, 0.15 mmol) and pure water (0.5 ml) at room temperature. The mixture was stirred, monitored by TLC. The mixture was quenched with a saturated aqueous NaHCO₃ solution and extracted by ethyl acetate (3× ml). The resulting solvent was removed in vacuo to yield the crude product. Purification by silica gel chromatography using 100 ~200 mesh ZCX II eluted by hexane-ethyl acetate (3:1, v/v) gave the yellow solid (70 mg, yield 63%). The crystalline compound was obtained through the slow volatilization of ethyl acetate containing the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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) and PLATON (Spek, 2003).

Figures top

	Fig. 1. View of the title molecular structure with atom numbering scheme and 30% probability displacement ellipsoids for non-hydrogen atoms.
	Fig. 2. View of the one-dimension chain along the a axis by intermolecular O—H···O hydrogen bonds.

(2R,3R)-2-[(4-Chlorophenyl)hydroxymethyl]cyclopentanone top

Crystal data top

C₁₂H₁₃ClO₂	F(000) = 472
M_r = 224.67	D_x = 1.365 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2189 reflections
a = 5.7401 (1) Å	θ = 4.9–76.7°
b = 10.4549 (2) Å	µ = 2.90 mm⁻¹
c = 18.2135 (3) Å	T = 150 K
V = 1093.03 (3) Å³	Block, colorless
Z = 4	0.43 × 0.31 × 0.25 mm

Data collection top

Bruker APEXII CCD diffractometer	1936 independent reflections
Radiation source: fine-focus sealed tube	1865 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 76.7°, θ_min = 4.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→5
T_min = 0.336, T_max = 0.484	k = −9→12
3762 measured reflections	l = −22→17

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.168	w = 1/[σ²(F_o²) + (0.0962P)² + 1.0311P] where P = (F_o² + 2F_c²)/3
S = 1.14	(Δ/σ)_max < 0.001
1936 reflections	Δρ_max = 0.34 e Å⁻³
146 parameters	Δρ_min = −0.52 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 572 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.09 (3)

Crystal data top

C₁₂H₁₃ClO₂	V = 1093.03 (3) Å³
M_r = 224.67	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 5.7401 (1) Å	µ = 2.90 mm⁻¹
b = 10.4549 (2) Å	T = 150 K
c = 18.2135 (3) Å	0.43 × 0.31 × 0.25 mm

Data collection top

Bruker APEXII CCD diffractometer	1936 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1865 reflections with I > 2σ(I)
T_min = 0.336, T_max = 0.484	R_int = 0.040
3762 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.168	Δρ_max = 0.34 e Å⁻³
S = 1.14	Δρ_min = −0.52 e Å⁻³
1936 reflections	Absolute structure: Flack (1983), 572 Friedel pairs
146 parameters	Absolute structure parameter: 0.09 (3)
0 restraints

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
O1	0.0477 (5)	0.4383 (3)	0.06246 (17)	0.0418 (7)
O2	0.5454 (4)	0.3133 (2)	−0.01098 (14)	0.0355 (6)
C3	−0.0344 (7)	0.7839 (4)	0.1635 (2)	0.0361 (8)
H3A	−0.1615	0.7951	0.1962	0.043*
C11	0.5311 (6)	0.3306 (3)	0.0549 (2)	0.0303 (7)
C2	0.0105 (6)	0.6644 (3)	0.1340 (2)	0.0324 (7)
H2A	−0.0858	0.5940	0.1469	0.039*
C6	0.2476 (6)	0.5168 (3)	0.05323 (19)	0.0291 (7)
H6A	0.283 (8)	0.528 (4)	−0.005 (2)	0.035*
C10	0.5749 (7)	0.2346 (3)	0.1141 (2)	0.0388 (8)
H10A	0.7174	0.1845	0.1036	0.047*
H10B	0.4415	0.1751	0.1188	0.047*
C12	0.2900 (8)	0.8713 (4)	0.0969 (2)	0.0423 (9)
H12A	0.3851	0.9420	0.0837	0.051*
C5	0.3327 (7)	0.7509 (3)	0.0683 (2)	0.0373 (8)
H5A	0.4601	0.7397	0.0356	0.045*
C1	0.1955 (6)	0.6465 (3)	0.08574 (18)	0.0288 (7)
C7	0.4634 (6)	0.4583 (4)	0.08953 (19)	0.0322 (7)
H7A	0.595 (8)	0.518 (5)	0.075 (2)	0.039*
C4	0.1048 (6)	0.8865 (3)	0.1455 (2)	0.0330 (7)
C9	0.6046 (7)	0.3132 (4)	0.1835 (2)	0.0443 (9)
H9A	0.7683	0.3411	0.1894	0.053*
H9B	0.5573	0.2637	0.2273	0.053*
C8	0.4435 (8)	0.4280 (4)	0.1717 (2)	0.0415 (9)
H8A	0.4946	0.5019	0.2017	0.050*
H8B	0.2810	0.4063	0.1850	0.050*
Cl1	0.05251 (19)	1.03468 (8)	0.18560 (5)	0.0445 (3)
H1	0.075 (14)	0.358 (6)	0.044 (4)	0.08 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0210 (11)	0.0328 (14)	0.0716 (18)	−0.0039 (11)	0.0011 (12)	−0.0157 (13)
O2	0.0268 (11)	0.0352 (13)	0.0444 (13)	0.0035 (11)	0.0001 (11)	−0.0124 (10)
C3	0.0272 (15)	0.042 (2)	0.0396 (17)	0.0004 (16)	0.0043 (14)	−0.0058 (15)
C11	0.0170 (13)	0.0257 (16)	0.0481 (18)	−0.0006 (13)	−0.0004 (13)	−0.0017 (13)
C2	0.0253 (15)	0.0308 (17)	0.0410 (17)	−0.0021 (13)	0.0015 (13)	−0.0030 (14)
C6	0.0192 (13)	0.0277 (17)	0.0403 (17)	−0.0022 (13)	−0.0007 (12)	−0.0057 (14)
C10	0.0382 (19)	0.0217 (16)	0.056 (2)	0.0033 (15)	0.0023 (17)	0.0028 (15)
C12	0.042 (2)	0.035 (2)	0.050 (2)	−0.0024 (17)	0.0116 (18)	0.0000 (17)
C5	0.0322 (17)	0.0246 (17)	0.055 (2)	−0.0013 (14)	0.0142 (17)	−0.0003 (16)
C1	0.0244 (14)	0.0285 (17)	0.0334 (16)	0.0043 (13)	−0.0034 (13)	−0.0020 (13)
C7	0.0235 (14)	0.0342 (18)	0.0388 (16)	0.0018 (16)	−0.0015 (13)	−0.0035 (14)
C4	0.0350 (17)	0.0255 (16)	0.0384 (16)	0.0065 (14)	0.0005 (14)	0.0027 (13)
C9	0.0403 (19)	0.046 (2)	0.047 (2)	0.0113 (18)	−0.0042 (17)	0.0053 (18)
C8	0.0411 (19)	0.044 (2)	0.0390 (17)	0.0109 (18)	−0.0030 (16)	−0.0057 (15)
Cl1	0.0542 (6)	0.0270 (4)	0.0522 (5)	0.0076 (4)	0.0046 (4)	−0.0052 (3)

Geometric parameters (Å, º) top

O1—C6	1.420 (4)	C10—H10B	0.9900
O1—H1	0.92 (7)	C12—C5	1.384 (6)
O2—C11	1.216 (4)	C12—C4	1.392 (5)
C3—C4	1.378 (5)	C12—H12A	0.9500
C3—C2	1.384 (5)	C5—C1	1.383 (5)
C3—H3A	0.9500	C5—H5A	0.9500
C11—C10	1.494 (5)	C7—C8	1.534 (5)
C11—C7	1.528 (5)	C7—H7A	1.01 (5)
C2—C1	1.392 (5)	C4—Cl1	1.739 (4)
C2—H2A	0.9500	C9—C8	1.530 (5)
C6—C1	1.510 (5)	C9—H9A	0.9900
C6—C7	1.531 (5)	C9—H9B	0.9900
C6—H6A	1.08 (4)	C8—H8A	0.9900
C10—C9	1.517 (6)	C8—H8B	0.9900
C10—H10A	0.9900

C6—O1—H1	111 (5)	C1—C5—H5A	119.0
C4—C3—C2	120.2 (3)	C12—C5—H5A	119.0
C4—C3—H3A	119.9	C5—C1—C2	118.3 (3)
C2—C3—H3A	119.9	C5—C1—C6	120.4 (3)
O2—C11—C10	126.9 (3)	C2—C1—C6	121.3 (3)
O2—C11—C7	123.7 (3)	C11—C7—C6	112.1 (3)
C10—C11—C7	109.3 (3)	C11—C7—C8	104.0 (3)
C3—C2—C1	120.5 (3)	C6—C7—C8	116.3 (3)
C3—C2—H2A	119.7	C11—C7—H7A	104 (3)
C1—C2—H2A	119.7	C6—C7—H7A	104 (3)
O1—C6—C1	108.2 (3)	C8—C7—H7A	115 (2)
O1—C6—C7	111.8 (3)	C3—C4—C12	120.3 (3)
C1—C6—C7	110.4 (3)	C3—C4—Cl1	119.6 (3)
O1—C6—H6A	109 (2)	C12—C4—Cl1	120.1 (3)
C1—C6—H6A	109 (2)	C10—C9—C8	103.9 (3)
C7—C6—H6A	108 (2)	C10—C9—H9A	111.0
C11—C10—C9	104.9 (3)	C8—C9—H9A	111.0
C11—C10—H10A	110.8	C10—C9—H9B	111.0
C9—C10—H10A	110.8	C8—C9—H9B	111.0
C11—C10—H10B	110.8	H9A—C9—H9B	109.0
C9—C10—H10B	110.8	C9—C8—C7	104.7 (3)
H10A—C10—H10B	108.8	C9—C8—H8A	110.8
C5—C12—C4	118.6 (4)	C7—C8—H8A	110.8
C5—C12—H12A	120.7	C9—C8—H8B	110.8
C4—C12—H12A	120.7	C7—C8—H8B	110.8
C1—C5—C12	122.0 (3)	H8A—C8—H8B	108.9

C4—C3—C2—C1	−0.3 (5)	O2—C11—C7—C8	173.9 (4)
O2—C11—C10—C9	163.5 (4)	C10—C11—C7—C8	−6.1 (4)
C7—C11—C10—C9	−16.5 (4)	O1—C6—C7—C11	63.0 (4)
C4—C12—C5—C1	0.8 (7)	C1—C6—C7—C11	−176.4 (3)
C12—C5—C1—C2	−0.4 (6)	O1—C6—C7—C8	−56.5 (4)
C12—C5—C1—C6	179.9 (4)	C1—C6—C7—C8	64.1 (4)
C3—C2—C1—C5	0.1 (5)	C2—C3—C4—C12	0.7 (6)
C3—C2—C1—C6	179.8 (3)	C2—C3—C4—Cl1	−177.7 (3)
O1—C6—C1—C5	−163.3 (3)	C5—C12—C4—C3	−1.0 (6)
C7—C6—C1—C5	74.0 (4)	C5—C12—C4—Cl1	177.4 (3)
O1—C6—C1—C2	17.0 (4)	C11—C10—C9—C8	32.5 (4)
C7—C6—C1—C2	−105.7 (4)	C10—C9—C8—C7	−36.6 (4)
O2—C11—C7—C6	47.5 (4)	C11—C7—C8—C9	26.1 (4)
C10—C11—C7—C6	−132.5 (3)	C6—C7—C8—C9	149.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.92 (7)	1.89 (7)	2.793 (4)	165 (7)
C10—H10A···O2ⁱⁱ	0.99	2.53	3.328 (5)	138
C5—H5A···Cg2ⁱⁱⁱ	0.95	2.96	3.818 (4)	150

Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) x+1/2, −y+1/2, −z; (iii) −x, y+3/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₃ClO₂
M_r	224.67
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	150
a, b, c (Å)	5.7401 (1), 10.4549 (2), 18.2135 (3)
V (Å³)	1093.03 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.90
Crystal size (mm)	0.43 × 0.31 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.336, 0.484
No. of measured, independent and observed [I > 2σ(I)] reflections	3762, 1936, 1865
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.168, 1.14
No. of reflections	1936
No. of parameters	146
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.52
Absolute structure	Flack (1983), 572 Friedel pairs
Absolute structure parameter	0.09 (3)

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.92 (7)	1.89 (7)	2.793 (4)	165 (7)
C10—H10A···O2ⁱⁱ	0.99	2.53	3.328 (5)	138
C5—H5A···Cg2ⁱⁱⁱ	0.95	2.96	3.818 (4)	150

Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) x+1/2, −y+1/2, −z; (iii) −x, y+3/2, −z+1/2.

Acknowledgements

This work was supported by the Doctoral Foundation and Cultivatable Foundation (2008-PYJJ-011) of Luoyang Normal University.

References

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