[2-(4-Chloro­phen­yl)-5-phenyl­oxolan-3-yl](cyclo­penten­yl)methanone

Lee, J.K.; Chavre, S.N.; Cho, Y.S.; Lee, Y.; Cha, J.H.

doi:10.1107/S1600536811051993

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o45

doi:10.1107/S1600536811051993

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[2-(4-Chlorophenyl)-5-phenyloxolan-3-yl](cyclopentenyl)methanone

Jae Kyun Lee,^a Satish N. Chavre,^a Yong Seo Cho,^a Yeonhee Lee ^b and Joo Hwan Cha ^b ^*

^aCenter for Neuro-Medicine, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, and ^bAdvanced Analysis Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea
^*Correspondence e-mail: jhcha@kist.re.kr

(Received 23 November 2011; accepted 2 December 2011; online 7 December 2011)

In the title compound, C₂₂H₂₁ClO₂, the oxolane ring adopts a twisted conformation. The dihedral angles between the mean plane of the oxolane ring and the mean planes of the 4-chlorophenyl, phenyl and cyclopentenyl rings are 71.81 (18), 76.9 (18) and 82.08 (18)°, respectively.

Related literature

For general background to the Prins-type cyclization for the synthesis of oxolanes, see: Chavre et al. (2006 , 2008 ); Cohen et al. (2001 ); Shin et al. (2005 ).

Experimental

Crystal data

C₂₂H₂₁ClO₂
M_r = 352.86
Monoclinic, P 2₁ /n
a = 5.7575 (6) Å
b = 11.3547 (12) Å
c = 28.554 (3) Å
β = 94.442 (8)°
V = 1861.1 (4) Å³
Z = 4
Cu Kα radiation
μ = 1.90 mm⁻¹
T = 296 K
0.50 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 ) T_min = 0.301, T_max = 0.684
18544 measured reflections
3363 independent reflections
2012 reflections with F² > 2σ(F²)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.139
S = 1.05
3363 reflections
230 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 2006 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SIR2008 in Il Milione (Burla et al., 2007 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: CrystalStructure (Rigaku, 2010 ); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811051993/go2037sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811051993/go2037Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811051993/go2037Isup3.cml

checkCIF report

Comment top

The oxolane moiety is an important heterocycle constituent in many bioactive natural products. New synthetic methodologies for 2,5-disubstituted oxolanes having an allenyl group, via Prins-type cyclization, has been subject of development since last decade (Shin et al., 2005). Cohen and colleagues synthesized the polysubstituted oxolane by Prins-Pinacol reaction (Cohen et al., 2001). 5-Exocyclic products, 2,3,5-trisustituted oxolanes, were synthesized from homopropargylic alcohols with alkynes and aldehydes (Chavre et al., 2006, 2008).

In the molecule of Fig. 1, the oxolane ring adopts a twisted conformation on C5–O1. The dihedral angle between the chlorophenyl and cyclopentenyl rings is 31.03 (17)°.

Related literature top

For general background to the Prins-type cyclization for the synthesis of oxolanes, see: Chavre et al. (2006, 2008); Cohen et al. (2001); Shin et al. (2005).

Experimental top

To a stirred solution of 1-(4-hydroxy-4-phenylbut-1-ynyl)cyclopentanol (0.31 mmol) and 4-Chlorobenzaldehyde (0.37 mmol) in dry diethyl ether (3.0 ml) was added slowly TMSOTf (0.93 mmol) for 10 min and stirred for 1 h at -78°C. The mixture was allowed to warm to room temperature slowly for 3 h. The mixture was stirred at room temperature for additional 1–2 h until the completion of reaction. The reaction mixture was quenched with saturated aqueous NaHCO₃ and diluted with 10 ml of diethyl ether. The organic solution was washed with water and brine, and the organic layer was dried over MgSO₄, filtered, concentrated and purification by silica gel column chromatography to afford the title compound (54%) as a yellow crystal.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: Il Milione (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top

Fig. 1. The structure of the title compound, with displacement ellipsoids drawn at the 50% probability level and H atoms with arbitrary radius.

[2-(4-Chlorophenyl)-5-phenyloxolan-3-yl](cyclopentenyl)methanone top

Crystal data top

C₂₂H₂₁ClO₂	F(000) = 744.00
M_r = 352.86	D_x = 1.259 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2yn	Cell parameters from 12997 reflections
a = 5.7575 (6) Å	θ = 3.1–68.3°
b = 11.3547 (12) Å	µ = 1.90 mm⁻¹
c = 28.554 (3) Å	T = 296 K
β = 94.442 (8)°	Needle, yellow
V = 1861.1 (4) Å³	0.50 × 0.20 × 0.20 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	2012 reflections with F² > 2σ(F²)
Detector resolution: 10.000 pixels mm^-1	R_int = 0.073
ω scans	θ_max = 68.2°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	h = −6→6
T_min = 0.301, T_max = 0.684	k = −13→13
18544 measured reflections	l = −34→34
3363 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0568P)² + 0.1808P] where P = (F_o² + 2F_c²)/3
3363 reflections	(Δ/σ)_max = 0.001
230 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₂H₂₁ClO₂	V = 1861.1 (4) Å³
M_r = 352.86	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 5.7575 (6) Å	µ = 1.90 mm⁻¹
b = 11.3547 (12) Å	T = 296 K
c = 28.554 (3) Å	0.50 × 0.20 × 0.20 mm
β = 94.442 (8)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3363 independent reflections
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	2012 reflections with F² > 2σ(F²)
T_min = 0.301, T_max = 0.684	R_int = 0.073
18544 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.20 e Å⁻³
3363 reflections	Δρ_min = −0.19 e Å⁻³
230 parameters

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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl(1)	0.34139 (17)	0.11812 (7)	0.53247 (3)	0.1065 (4)
O(1)	0.2994 (3)	0.37307 (13)	0.74183 (5)	0.0597 (5)
O(2)	0.6450 (3)	0.53421 (16)	0.66245 (6)	0.0763 (6)
C(2)	0.1844 (5)	0.4198 (2)	0.70022 (8)	0.0574 (7)
C(3)	0.2806 (5)	0.5488 (2)	0.69627 (8)	0.0561 (7)
C(4)	0.4071 (5)	0.5703 (3)	0.74448 (8)	0.0700 (8)
C(5)	0.3328 (5)	0.4685 (3)	0.77457 (8)	0.0602 (7)
C(6)	0.5050 (5)	0.4344 (2)	0.81393 (8)	0.0541 (6)
C(7)	0.7050 (5)	0.3738 (3)	0.80578 (10)	0.0682 (8)
C(8)	0.8695 (5)	0.3488 (3)	0.84223 (12)	0.0802 (9)
C(9)	0.8361 (6)	0.3839 (3)	0.88696 (11)	0.0805 (9)
C(10)	0.6385 (6)	0.4435 (3)	0.89575 (9)	0.0795 (9)
C(11)	0.4730 (5)	0.4682 (3)	0.85944 (9)	0.0668 (7)
C(12)	0.2209 (5)	0.3392 (2)	0.65941 (8)	0.0526 (6)
C(13)	0.0550 (5)	0.3341 (3)	0.62177 (9)	0.0628 (7)
C(14)	0.0916 (5)	0.2667 (3)	0.58285 (9)	0.0713 (8)
C(15)	0.2948 (6)	0.2045 (3)	0.58140 (9)	0.0680 (8)
C(16)	0.4618 (5)	0.2066 (3)	0.61850 (10)	0.0697 (8)
C(17)	0.4230 (5)	0.2737 (2)	0.65745 (9)	0.0632 (7)
C(18)	0.4382 (5)	0.5586 (2)	0.65654 (8)	0.0549 (6)
C(19)	0.3382 (5)	0.5935 (2)	0.60977 (8)	0.0523 (6)
C(20)	0.1393 (5)	0.6481 (3)	0.59902 (9)	0.0667 (8)
C(21)	0.1054 (6)	0.6755 (3)	0.54765 (9)	0.0881 (10)
C(22)	0.3045 (6)	0.6163 (4)	0.52732 (10)	0.0999 (11)
C(23)	0.4688 (5)	0.5744 (3)	0.56742 (9)	0.0829 (9)
H(2)	0.0171	0.4240	0.7043	0.0689*
H(3)	0.1505	0.6041	0.6912	0.0673*
H(4A)	0.5746	0.5702	0.7426	0.0840*
H(4B)	0.3612	0.6451	0.7573	0.0840*
H(5)	0.1839	0.4877	0.7872	0.0723*
H(7)	0.7295	0.3495	0.7755	0.0818*
H(8)	1.0039	0.3077	0.8363	0.0963*
H(9)	0.9478	0.3673	0.9113	0.0966*
H(10)	0.6151	0.4674	0.9262	0.0954*
H(11)	0.3380	0.5083	0.8657	0.0802*
H(13)	−0.0827	0.3765	0.6227	0.0753*
H(14)	−0.0211	0.2635	0.5577	0.0855*
H(16)	0.5987	0.1636	0.6174	0.0836*
H(17)	0.5345	0.2749	0.6828	0.0758*
H(21A)	−0.0419	0.6444	0.5342	0.1057*
H(21B)	0.1090	0.7598	0.5423	0.1057*
H(22A)	0.3833	0.6710	0.5078	0.1199*
H(22B)	0.2495	0.5501	0.5081	0.1199*
H(23A)	0.5063	0.4918	0.5638	0.0994*
H(23B)	0.6120	0.6198	0.5694	0.0994*
H(20)	0.033 (5)	0.672 (3)	0.6215 (9)	0.086 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl(1)	0.1507 (9)	0.0956 (7)	0.0744 (5)	0.0158 (6)	0.0156 (5)	−0.0156 (4)
O(1)	0.0594 (12)	0.0608 (11)	0.0580 (10)	−0.0031 (9)	−0.0002 (8)	0.0051 (8)
O(2)	0.0438 (12)	0.0850 (14)	0.1001 (14)	0.0143 (10)	0.0048 (10)	0.0100 (11)
C(2)	0.0435 (15)	0.0749 (17)	0.0541 (14)	0.0051 (13)	0.0051 (12)	0.0053 (12)
C(3)	0.0554 (16)	0.0592 (15)	0.0541 (14)	0.0195 (13)	0.0067 (12)	0.0033 (11)
C(4)	0.091 (2)	0.0526 (15)	0.0655 (16)	0.0113 (15)	−0.0014 (15)	−0.0010 (12)
C(5)	0.0540 (17)	0.0693 (17)	0.0580 (15)	0.0132 (13)	0.0085 (13)	−0.0031 (13)
C(6)	0.0498 (16)	0.0577 (14)	0.0546 (14)	0.0049 (12)	0.0032 (12)	0.0053 (11)
C(7)	0.0614 (19)	0.0715 (18)	0.0712 (17)	0.0147 (15)	0.0019 (14)	0.0040 (14)
C(8)	0.063 (2)	0.0660 (18)	0.109 (3)	0.0128 (15)	−0.0068 (18)	0.0108 (17)
C(9)	0.080 (3)	0.071 (2)	0.086 (3)	−0.0072 (17)	−0.0249 (18)	0.0174 (16)
C(10)	0.091 (3)	0.083 (2)	0.0624 (17)	−0.0093 (19)	−0.0075 (17)	−0.0003 (15)
C(11)	0.0663 (19)	0.0701 (17)	0.0639 (17)	0.0031 (14)	0.0038 (14)	−0.0034 (13)
C(12)	0.0423 (15)	0.0572 (14)	0.0580 (15)	−0.0024 (12)	0.0021 (12)	0.0057 (11)
C(13)	0.0521 (17)	0.0688 (17)	0.0670 (16)	0.0033 (14)	0.0018 (14)	0.0059 (13)
C(14)	0.077 (3)	0.0753 (19)	0.0592 (16)	0.0003 (16)	−0.0070 (15)	0.0029 (14)
C(15)	0.081 (3)	0.0638 (17)	0.0604 (16)	−0.0040 (16)	0.0129 (16)	0.0014 (13)
C(16)	0.0560 (18)	0.0653 (17)	0.089 (2)	0.0075 (14)	0.0120 (16)	−0.0044 (15)
C(17)	0.0489 (17)	0.0655 (16)	0.0741 (17)	0.0055 (13)	−0.0023 (13)	−0.0065 (13)
C(18)	0.0468 (16)	0.0497 (14)	0.0682 (16)	0.0050 (12)	0.0050 (13)	0.0004 (12)
C(19)	0.0449 (16)	0.0562 (14)	0.0567 (14)	−0.0011 (12)	0.0094 (12)	−0.0019 (11)
C(20)	0.0558 (18)	0.090 (2)	0.0554 (16)	0.0107 (16)	0.0102 (14)	0.0036 (14)
C(21)	0.073 (2)	0.132 (3)	0.0592 (17)	0.015 (2)	0.0067 (15)	0.0116 (17)
C(22)	0.093 (3)	0.146 (4)	0.0635 (19)	0.006 (3)	0.0223 (19)	−0.0039 (18)
C(23)	0.069 (2)	0.107 (3)	0.0762 (19)	0.0100 (18)	0.0269 (17)	−0.0053 (17)

Geometric parameters (Å, º) top

Cl(1)—C(15)	1.745 (3)	C(20)—C(21)	1.497 (4)
O(1)—C(2)	1.418 (3)	C(21)—C(22)	1.485 (5)
O(1)—C(5)	1.434 (3)	C(22)—C(23)	1.505 (4)
O(2)—C(18)	1.221 (3)	C(2)—H(2)	0.980
C(2)—C(3)	1.573 (4)	C(3)—H(3)	0.980
C(2)—C(12)	1.509 (4)	C(4)—H(4A)	0.970
C(3)—C(4)	1.526 (4)	C(4)—H(4B)	0.970
C(3)—C(18)	1.511 (4)	C(5)—H(5)	0.980
C(4)—C(5)	1.521 (4)	C(7)—H(7)	0.930
C(5)—C(6)	1.491 (4)	C(8)—H(8)	0.930
C(6)—C(7)	1.376 (4)	C(9)—H(9)	0.930
C(6)—C(11)	1.381 (4)	C(10)—H(10)	0.930
C(7)—C(8)	1.382 (4)	C(11)—H(11)	0.930
C(8)—C(9)	1.366 (5)	C(13)—H(13)	0.930
C(9)—C(10)	1.363 (5)	C(14)—H(14)	0.930
C(10)—C(11)	1.382 (4)	C(16)—H(16)	0.930
C(12)—C(13)	1.382 (4)	C(17)—H(17)	0.930
C(12)—C(17)	1.386 (4)	C(20)—H(20)	0.96 (3)
C(13)—C(14)	1.379 (4)	C(21)—H(21A)	0.970
C(14)—C(15)	1.370 (5)	C(21)—H(21B)	0.970
C(15)—C(16)	1.375 (4)	C(22)—H(22A)	0.970
C(16)—C(17)	1.380 (4)	C(22)—H(22B)	0.970
C(18)—C(19)	1.467 (4)	C(23)—H(23A)	0.970
C(19)—C(20)	1.318 (4)	C(23)—H(23B)	0.970
C(19)—C(23)	1.488 (4)

O(2)···C(2)ⁱ	3.460 (3)	H(8)···H(4A)^iv	3.5198
O(2)···C(8)ⁱⁱ	3.575 (4)	H(8)···H(4B)^iv	3.3875
O(2)···C(13)ⁱ	3.537 (4)	H(8)···H(5)ⁱ	2.7276
C(2)···O(2)ⁱⁱⁱ	3.460 (3)	H(8)···H(11)ⁱ	3.0564
C(8)···O(2)^iv	3.575 (4)	H(8)···H(23B)^iv	3.5412
C(8)···C(18)^iv	3.475 (4)	H(8)···H(20)^iv	3.2315
C(8)···C(19)^iv	3.572 (4)	H(9)···Cl(1)ⁱⁱ	3.4433
C(11)···C(15)^v	3.582 (4)	H(9)···Cl(1)^x	3.5629
C(13)···O(2)ⁱⁱⁱ	3.537 (4)	H(9)···C(19)^iv	3.4151
C(15)···C(11)^vi	3.582 (4)	H(9)···C(20)^iv	3.4699
C(18)···C(8)ⁱⁱ	3.475 (4)	H(9)···C(21)^iv	3.5022
C(19)···C(8)ⁱⁱ	3.572 (4)	H(9)···C(22)^iv	3.5828
Cl(1)···H(9)^iv	3.4433	H(9)···C(23)^iv	3.4077
Cl(1)···H(9)^vii	3.5629	H(9)···H(11)ⁱ	3.1235
Cl(1)···H(10)^vi	3.4222	H(9)···H(16)ⁱⁱ	3.4677
Cl(1)···H(10)^vii	3.3528	H(9)···H(21B)^iv	3.0383
Cl(1)···H(11)^vi	3.3964	H(9)···H(22A)^iv	3.3010
Cl(1)···H(21B)^viii	3.5133	H(9)···H(23B)^iv	2.8899
Cl(1)···H(22A)^ix	3.1389	H(10)···Cl(1)^v	3.4222
O(1)···H(4B)^vi	2.7496	H(10)···Cl(1)^x	3.3528
O(1)···H(7)ⁱⁱⁱ	3.4997	H(10)···C(15)^v	3.5757
O(1)···H(8)ⁱⁱⁱ	3.3806	H(10)···H(14)^v	3.4412
O(2)···H(2)ⁱ	2.6806	H(10)···H(16)ⁱⁱ	3.0881
O(2)···H(3)ⁱ	3.0662	H(10)···H(21B)^vi	2.8666
O(2)···H(8)ⁱⁱ	3.2230	H(11)···Cl(1)^v	3.3964
O(2)···H(13)ⁱ	2.6883	H(11)···C(8)ⁱⁱⁱ	3.2748
O(2)···H(20)ⁱ	3.03 (3)	H(11)···C(9)ⁱⁱⁱ	3.3137
C(2)···H(4B)^vi	3.3645	H(11)···C(14)^v	3.2922
C(3)···H(8)ⁱⁱ	3.3504	H(11)···C(15)^v	2.8298
C(5)···H(8)ⁱⁱⁱ	3.2463	H(11)···C(16)^v	2.8939
C(6)···H(8)ⁱⁱⁱ	3.3292	H(11)···C(17)^v	3.4096
C(6)···H(20)^vi	3.52 (3)	H(11)···H(8)ⁱⁱⁱ	3.0564
C(7)···H(2)ⁱ	3.5722	H(11)···H(9)ⁱⁱⁱ	3.1235
C(7)···H(5)ⁱ	3.1280	H(11)···H(16)^v	3.1385
C(7)···H(20)^vi	3.44 (3)	H(13)···O(2)ⁱⁱⁱ	2.6883
C(8)···H(5)ⁱ	2.9455	H(13)···C(16)ⁱⁱⁱ	3.2505
C(8)···H(11)ⁱ	3.2748	H(13)···C(17)ⁱⁱⁱ	3.2991
C(8)···H(20)^vi	3.29 (3)	H(13)···H(16)ⁱⁱⁱ	3.0320
C(9)···H(11)ⁱ	3.3137	H(13)···H(17)ⁱⁱⁱ	3.1180
C(9)···H(16)ⁱⁱ	3.2006	H(13)···H(23A)ⁱⁱⁱ	3.0864
C(9)···H(23B)^iv	3.2533	H(13)···H(23B)ⁱⁱⁱ	3.5534
C(9)···H(20)^vi	3.20 (3)	H(14)···C(21)^viii	3.0892
C(10)···H(16)ⁱⁱ	2.9601	H(14)···C(22)^viii	3.1317
C(10)···H(21B)^vi	3.1472	H(14)···H(10)^vi	3.4412
C(10)···H(20)^vi	3.26 (3)	H(14)···H(16)ⁱⁱⁱ	3.0912
C(11)···H(8)ⁱⁱⁱ	3.2826	H(14)···H(21A)^viii	2.8734
C(11)···H(16)ⁱⁱ	3.3447	H(14)···H(21B)^viii	2.8730
C(11)···H(20)^vi	3.41 (3)	H(14)···H(22A)^viii	2.7927
C(12)···H(4B)^vi	3.3030	H(14)···H(22B)^viii	3.0585
C(13)···H(16)ⁱⁱⁱ	3.2583	H(16)···C(9)^iv	3.2006
C(14)···H(11)^vi	3.2922	H(16)···C(10)^iv	2.9601
C(14)···H(16)ⁱⁱⁱ	3.2907	H(16)···C(11)^iv	3.3447
C(14)···H(21A)^viii	3.4806	H(16)···C(13)ⁱ	3.2583
C(15)···H(10)^vi	3.5757	H(16)···C(14)ⁱ	3.2907
C(15)···H(11)^vi	2.8298	H(16)···H(9)^iv	3.4677
C(15)···H(22A)^ix	3.5571	H(16)···H(10)^iv	3.0881
C(16)···H(11)^vi	2.8939	H(16)···H(11)^vi	3.1385
C(16)···H(13)ⁱ	3.2505	H(16)···H(13)ⁱ	3.0320
C(17)···H(4B)^vi	3.3692	H(16)···H(14)ⁱ	3.0912
C(17)···H(11)^vi	3.4096	H(17)···H(2)ⁱ	3.2711
C(17)···H(13)ⁱ	3.2991	H(17)···H(4B)^vi	3.2998
C(18)···H(8)ⁱⁱ	2.8538	H(17)···H(13)ⁱ	3.1180
C(19)···H(8)ⁱⁱ	2.9837	H(21A)···C(14)^viii	3.4806
C(19)···H(9)ⁱⁱ	3.4151	H(21A)···C(23)ⁱⁱⁱ	3.1440
C(20)···H(8)ⁱⁱ	3.2142	H(21A)···H(14)^viii	2.8734
C(20)···H(9)ⁱⁱ	3.4699	H(21A)···H(22A)ⁱⁱⁱ	3.3502
C(20)···H(23B)ⁱⁱⁱ	3.1048	H(21A)···H(22B)^viii	2.7457
C(21)···H(9)ⁱⁱ	3.5022	H(21A)···H(23A)ⁱⁱⁱ	3.2912
C(21)···H(14)^viii	3.0892	H(21A)···H(23B)ⁱⁱⁱ	2.3173
C(21)···H(22B)^viii	3.5726	H(21B)···Cl(1)^viii	3.5133
C(21)···H(23B)ⁱⁱⁱ	3.0209	H(21B)···C(10)^v	3.1472
C(22)···H(9)ⁱⁱ	3.5828	H(21B)···H(9)ⁱⁱ	3.0383
C(22)···H(14)^viii	3.1317	H(21B)···H(10)^v	2.8666
C(22)···H(22B)^ix	3.4041	H(21B)···H(14)^viii	2.8730
C(22)···H(23A)^ix	3.1476	H(21B)···H(23B)ⁱⁱⁱ	3.4145
C(23)···H(9)ⁱⁱ	3.4077	H(22A)···Cl(1)^ix	3.1389
C(23)···H(21A)ⁱ	3.1440	H(22A)···C(15)^ix	3.5571
C(23)···H(22B)^ix	3.1328	H(22A)···H(9)ⁱⁱ	3.3010
H(2)···O(2)ⁱⁱⁱ	2.6806	H(22A)···H(14)^viii	2.7927
H(2)···C(7)ⁱⁱⁱ	3.5722	H(22A)···H(21A)ⁱ	3.3502
H(2)···H(4A)ⁱⁱⁱ	3.2970	H(22A)···H(22B)^ix	3.3354
H(2)···H(4B)^vi	3.4065	H(22A)···H(23A)^ix	2.8646
H(2)···H(7)ⁱⁱⁱ	2.8478	H(22B)···C(21)^viii	3.5726
H(2)···H(17)ⁱⁱⁱ	3.2711	H(22B)···C(22)^ix	3.4041
H(3)···O(2)ⁱⁱⁱ	3.0662	H(22B)···C(23)^ix	3.1328
H(3)···H(8)ⁱⁱ	3.1877	H(22B)···H(14)^viii	3.0585
H(4A)···H(2)ⁱ	3.2970	H(22B)···H(21A)^viii	2.7457
H(4A)···H(7)ⁱⁱ	3.4183	H(22B)···H(22A)^ix	3.3354
H(4A)···H(8)ⁱⁱ	3.5198	H(22B)···H(22B)^viii	3.0914
H(4B)···O(1)^v	2.7496	H(22B)···H(22B)^ix	3.1672
H(4B)···C(2)^v	3.3645	H(22B)···H(23A)^ix	2.6197
H(4B)···C(12)^v	3.3030	H(22B)···H(23B)^ix	3.0847
H(4B)···C(17)^v	3.3692	H(23A)···C(22)^ix	3.1476
H(4B)···H(2)^v	3.4065	H(23A)···H(13)ⁱ	3.0864
H(4B)···H(7)ⁱⁱ	3.4863	H(23A)···H(21A)ⁱ	3.2912
H(4B)···H(8)ⁱⁱ	3.3875	H(23A)···H(22A)^ix	2.8646
H(4B)···H(17)^v	3.2998	H(23A)···H(22B)^ix	2.6197
H(5)···C(7)ⁱⁱⁱ	3.1280	H(23B)···C(9)ⁱⁱ	3.2533
H(5)···C(8)ⁱⁱⁱ	2.9455	H(23B)···C(20)ⁱ	3.1048
H(5)···H(7)ⁱⁱⁱ	3.0467	H(23B)···C(21)ⁱ	3.0209
H(5)···H(8)ⁱⁱⁱ	2.7276	H(23B)···H(8)ⁱⁱ	3.5412
H(7)···O(1)ⁱ	3.4997	H(23B)···H(9)ⁱⁱ	2.8899
H(7)···H(2)ⁱ	2.8478	H(23B)···H(13)ⁱ	3.5534
H(7)···H(4A)^iv	3.4183	H(23B)···H(21A)ⁱ	2.3173
H(7)···H(4B)^iv	3.4863	H(23B)···H(21B)ⁱ	3.4145
H(7)···H(5)ⁱ	3.0467	H(23B)···H(22B)^ix	3.0847
H(8)···O(1)ⁱ	3.3806	H(23B)···H(20)ⁱ	2.8072
H(8)···O(2)^iv	3.2230	H(20)···O(2)ⁱⁱⁱ	3.03 (3)
H(8)···C(3)^iv	3.3504	H(20)···C(6)^v	3.52 (3)
H(8)···C(5)ⁱ	3.2463	H(20)···C(7)^v	3.44 (3)
H(8)···C(6)ⁱ	3.3292	H(20)···C(8)^v	3.29 (3)
H(8)···C(11)ⁱ	3.2826	H(20)···C(9)^v	3.20 (3)
H(8)···C(18)^iv	2.8538	H(20)···C(10)^v	3.26 (3)
H(8)···C(19)^iv	2.9837	H(20)···C(11)^v	3.41 (3)
H(8)···C(20)^iv	3.2142	H(20)···H(8)ⁱⁱ	3.2315
H(8)···H(3)^iv	3.1877	H(20)···H(23B)ⁱⁱⁱ	2.8072

C(2)—O(1)—C(5)	107.08 (17)	C(18)—C(3)—H(3)	109.756
O(1)—C(2)—C(3)	105.33 (18)	C(3)—C(4)—H(4A)	110.822
O(1)—C(2)—C(12)	109.62 (19)	C(3)—C(4)—H(4B)	110.830
C(3)—C(2)—C(12)	116.0 (2)	C(5)—C(4)—H(4A)	110.820
C(2)—C(3)—C(4)	103.30 (19)	C(5)—C(4)—H(4B)	110.820
C(2)—C(3)—C(18)	110.98 (19)	H(4A)—C(4)—H(4B)	108.881
C(4)—C(3)—C(18)	113.2 (2)	O(1)—C(5)—H(5)	109.307
C(3)—C(4)—C(5)	104.6 (2)	C(4)—C(5)—H(5)	109.305
O(1)—C(5)—C(4)	103.60 (18)	C(6)—C(5)—H(5)	109.316
O(1)—C(5)—C(6)	110.1 (2)	C(6)—C(7)—H(7)	119.692
C(4)—C(5)—C(6)	115.0 (2)	C(8)—C(7)—H(7)	119.701
C(5)—C(6)—C(7)	121.2 (3)	C(7)—C(8)—H(8)	119.783
C(5)—C(6)—C(11)	120.5 (3)	C(9)—C(8)—H(8)	119.795
C(7)—C(6)—C(11)	118.2 (3)	C(8)—C(9)—H(9)	120.091
C(6)—C(7)—C(8)	120.6 (3)	C(10)—C(9)—H(9)	120.106
C(7)—C(8)—C(9)	120.4 (3)	C(9)—C(10)—H(10)	120.016
C(8)—C(9)—C(10)	119.8 (3)	C(11)—C(10)—H(10)	120.013
C(9)—C(10)—C(11)	120.0 (3)	C(6)—C(11)—H(11)	119.505
C(6)—C(11)—C(10)	121.0 (3)	C(10)—C(11)—H(11)	119.501
C(2)—C(12)—C(13)	119.8 (3)	C(12)—C(13)—H(13)	119.632
C(2)—C(12)—C(17)	121.6 (2)	C(14)—C(13)—H(13)	119.645
C(13)—C(12)—C(17)	118.5 (3)	C(13)—C(14)—H(14)	120.183
C(12)—C(13)—C(14)	120.7 (3)	C(15)—C(14)—H(14)	120.201
C(13)—C(14)—C(15)	119.6 (3)	C(15)—C(16)—H(16)	120.539
Cl(1)—C(15)—C(14)	119.9 (2)	C(17)—C(16)—H(16)	120.562
Cl(1)—C(15)—C(16)	119.0 (3)	C(12)—C(17)—H(17)	119.414
C(14)—C(15)—C(16)	121.1 (3)	C(16)—C(17)—H(17)	119.421
C(15)—C(16)—C(17)	118.9 (3)	C(19)—C(20)—H(20)	124.5 (15)
C(12)—C(17)—C(16)	121.2 (3)	C(21)—C(20)—H(20)	123.6 (15)
O(2)—C(18)—C(3)	121.0 (2)	C(20)—C(21)—H(21A)	110.941
O(2)—C(18)—C(19)	119.8 (3)	C(20)—C(21)—H(21B)	110.944
C(3)—C(18)—C(19)	119.2 (3)	C(22)—C(21)—H(21A)	110.955
C(18)—C(19)—C(20)	127.7 (3)	C(22)—C(21)—H(21B)	110.945
C(18)—C(19)—C(23)	120.9 (3)	H(21A)—C(21)—H(21B)	108.957
C(20)—C(19)—C(23)	111.3 (3)	C(21)—C(22)—H(22A)	110.164
C(19)—C(20)—C(21)	111.8 (3)	C(21)—C(22)—H(22B)	110.161
C(20)—C(21)—C(22)	104.1 (3)	C(23)—C(22)—H(22A)	110.158
C(21)—C(22)—C(23)	107.7 (3)	C(23)—C(22)—H(22B)	110.167
C(19)—C(23)—C(22)	104.2 (3)	H(22A)—C(22)—H(22B)	108.463
O(1)—C(2)—H(2)	108.562	C(19)—C(23)—H(23A)	110.912
C(3)—C(2)—H(2)	108.556	C(19)—C(23)—H(23B)	110.920
C(12)—C(2)—H(2)	108.535	C(22)—C(23)—H(23A)	110.929
C(2)—C(3)—H(3)	109.737	C(22)—C(23)—H(23B)	110.927
C(4)—C(3)—H(3)	109.735	H(23A)—C(23)—H(23B)	108.947

C(2)—O(1)—C(5)—C(4)	−41.7 (2)	C(11)—C(6)—C(7)—C(8)	−0.6 (4)
C(2)—O(1)—C(5)—C(6)	−165.24 (17)	C(6)—C(7)—C(8)—C(9)	−0.0 (4)
C(5)—O(1)—C(2)—C(3)	34.0 (2)	C(7)—C(8)—C(9)—C(10)	0.4 (5)
C(5)—O(1)—C(2)—C(12)	159.47 (17)	C(8)—C(9)—C(10)—C(11)	−0.1 (5)
O(1)—C(2)—C(3)—C(4)	−12.5 (3)	C(9)—C(10)—C(11)—C(6)	−0.6 (5)
O(1)—C(2)—C(3)—C(18)	109.02 (18)	C(2)—C(12)—C(13)—C(14)	175.9 (2)
O(1)—C(2)—C(12)—C(13)	151.51 (18)	C(2)—C(12)—C(17)—C(16)	−175.4 (2)
O(1)—C(2)—C(12)—C(17)	−31.7 (3)	C(13)—C(12)—C(17)—C(16)	1.4 (4)
C(3)—C(2)—C(12)—C(13)	−89.4 (3)	C(17)—C(12)—C(13)—C(14)	−1.0 (4)
C(3)—C(2)—C(12)—C(17)	87.4 (3)	C(12)—C(13)—C(14)—C(15)	−0.2 (4)
C(12)—C(2)—C(3)—C(4)	−133.95 (19)	C(13)—C(14)—C(15)—Cl(1)	179.5 (2)
C(12)—C(2)—C(3)—C(18)	−12.4 (3)	C(13)—C(14)—C(15)—C(16)	1.1 (4)
C(2)—C(3)—C(4)—C(5)	−11.7 (3)	Cl(1)—C(15)—C(16)—C(17)	−179.07 (17)
C(2)—C(3)—C(18)—O(2)	−85.7 (3)	C(14)—C(15)—C(16)—C(17)	−0.6 (4)
C(2)—C(3)—C(18)—C(19)	91.9 (3)	C(15)—C(16)—C(17)—C(12)	−0.6 (4)
C(4)—C(3)—C(18)—O(2)	29.9 (3)	O(2)—C(18)—C(19)—C(20)	−162.7 (2)
C(4)—C(3)—C(18)—C(19)	−152.55 (18)	O(2)—C(18)—C(19)—C(23)	13.7 (4)
C(18)—C(3)—C(4)—C(5)	−131.75 (19)	C(3)—C(18)—C(19)—C(20)	19.7 (4)
C(3)—C(4)—C(5)—O(1)	31.9 (3)	C(3)—C(18)—C(19)—C(23)	−163.86 (18)
C(3)—C(4)—C(5)—C(6)	152.05 (19)	C(18)—C(19)—C(20)—C(21)	176.2 (2)
O(1)—C(5)—C(6)—C(7)	42.3 (3)	C(18)—C(19)—C(23)—C(22)	177.59 (19)
O(1)—C(5)—C(6)—C(11)	−140.95 (19)	C(20)—C(19)—C(23)—C(22)	−5.5 (3)
C(4)—C(5)—C(6)—C(7)	−74.2 (3)	C(23)—C(19)—C(20)—C(21)	−0.5 (3)
C(4)—C(5)—C(6)—C(11)	102.5 (3)	C(19)—C(20)—C(21)—C(22)	6.3 (4)
C(5)—C(6)—C(7)—C(8)	176.2 (2)	C(20)—C(21)—C(22)—C(23)	−9.4 (4)
C(5)—C(6)—C(11)—C(10)	−175.9 (2)	C(21)—C(22)—C(23)—C(19)	9.2 (4)
C(7)—C(6)—C(11)—C(10)	0.9 (4)

Symmetry codes: (i) x+1, y, z; (ii) −x+3/2, y+1/2, −z+3/2; (iii) x−1, y, z; (iv) −x+3/2, y−1/2, −z+3/2; (v) −x+1/2, y+1/2, −z+3/2; (vi) −x+1/2, y−1/2, −z+3/2; (vii) x−1/2, −y+1/2, z−1/2; (viii) −x, −y+1, −z+1; (ix) −x+1, −y+1, −z+1; (x) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₁ClO₂
M_r	352.86
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	5.7575 (6), 11.3547 (12), 28.554 (3)
β (°)	94.442 (8)
V (Å³)	1861.1 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.90
Crystal size (mm)	0.50 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Rigaku, 1995)
T_min, T_max	0.301, 0.684
No. of measured, independent and observed [F² > 2σ(F²)] reflections	18544, 3363, 2012
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.139, 1.05
No. of reflections	3363
No. of parameters	230
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.19

Computer programs: RAPID-AUTO (Rigaku, 2006), Il Milione (Burla et al., 2007), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).

Acknowledgements

Fiancial support from the Korea Institute of Science and Technology (KIST) is gratefully acknowledged.

References

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