[2-(4-Chloro-phen-yl)-5-phenyl-oxolan-3-yl](cyclo-penten-yl)methanone.

In the title compound, C(22)H(21)ClO(2), 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-chloro-phenyl, phenyl and cyclo-pentenyl 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 = 352.86

Monoclinic,

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 F 2 > 2σ(F 2)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.139

S = 1.05

3363 reflections

230 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811051993/go2037sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811051993/go2037Isup3.cml

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

C22H21ClO2	F(000) = 744.00
Mr = 352.86	Dx = 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

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

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(Fo2) + (0.0568P)2 + 0.1808P] where P = (Fo2 + 2Fc2)/3
3363 reflections	(Δ/σ)max = 0.001
230 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods

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).

	x	y	z	Uiso*/Ueq
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)*

	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)

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)