Crystal structure of (E)-1-(4-chloro-phen-yl)ethanone O-de-hydro-abietyloxime.

The title compound, C28H34ClNO2 {systematic name: (E)-1-(4-chloro-phen-yl)ethanone O-[(1R,4aS,10aR)-7-isopropyl-1,4a-di-methyl-1,2,3,4,4a,9,10,10a-octa-hydro-phenanthrene-1-carbonyl]oxime}, was synthesized from de-hydro-abietic acid. In the de-hydro-abietyl moiety, the central and terminal cyclo-hexane rings display chair and half-chair conformations, respectively, and a trans-ring junction. The C=N bond is in an E conformation and the C-O-N=C torsion angle is 148.1 (5)°. No directional inter-actions except van der Waals contacts occur in the crystal structure.

Related literature

For the biological activity of de­hydro­abietic acid derivatives, see: Cui et al. (2013 ▶); Rao et al. (2008 ▶); Sepulveda et al. (2005 ▶). For the crystal structures of de­hydro­abietic acid derivatives, see: Rao et al. (2006 ▶, 2009 ▶).

Experimental

Crystal data

C28H34ClNO2

M = 452.01

Orthorhombic,

a = 28.804 (6) Å

b = 6.1760 (12) Å

c = 13.922 (3) Å

V = 2476.6 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.948, T max = 0.982

5186 measured reflections

4554 independent reflections

2566 reflections with I > 2σ(I)

R int = 0.099

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.205

S = 1.00

4554 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 1911 Friedel pairs

Absolute structure parameter: 0.05 (16)

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536814015888/hb7249sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015888/hb7249Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S1600536814015888/hb7249fig1.tif

Mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

CCDC reference: 1012686

Additional supporting information: crystallographic information; 3D view; checkCIF report

C28H34ClNO2	F(000) = 968
Mr = 452.01	Dx = 1.212 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 28.804 (6) Å	θ = 9–13°
b = 6.1760 (12) Å	µ = 0.18 mm−1
c = 13.922 (3) Å	T = 293 K
V = 2476.6 (9) Å3	Block, colourless
Z = 4	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	2566 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.099
Graphite monochromator	θmax = 25.4°, θmin = 1.4°
ω/2θ scans	h = −34→34
Absorption correction: ψ scan (North et al., 1968)	k = 0→7
Tmin = 0.948, Tmax = 0.982	l = 0→16
5186 measured reflections	3 standard reflections every 200 reflections
4554 independent reflections	intensity decay: 1%

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)] = 0.069	H-atom parameters constrained
wR(F2) = 0.205	w = 1/[σ2(Fo2) + (0.1P)2 + 0.3P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
4554 reflections	Δρmax = 0.18 e Å−3
289 parameters	Δρmin = −0.23 e Å−3
0 restraints	Absolute structure: Flack (1983), 1911 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (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
Cl	0.59358 (6)	0.1759 (3)	0.58245 (11)	0.0903 (6)
N	0.41858 (16)	0.1075 (8)	0.2777 (4)	0.0786 (15)
O1	0.34454 (14)	0.3392 (7)	0.2493 (3)	0.0917 (14)
C1	0.0874 (3)	0.9817 (14)	0.1786 (7)	0.143 (4)
H1A	0.0598	1.0654	0.1890	0.214*
H1B	0.1088	1.0637	0.1403	0.214*
H1C	0.1014	0.9479	0.2393	0.214*
O2	0.38242 (13)	0.0305 (7)	0.2150 (3)	0.0774 (12)
C2	0.0380 (2)	0.6446 (14)	0.1772 (5)	0.106 (2)
H2A	0.0303	0.5175	0.1409	0.159*
H2B	0.0109	0.7334	0.1844	0.159*
H2C	0.0492	0.6028	0.2394	0.159*
C3	0.07480 (18)	0.7692 (9)	0.1256 (4)	0.0707 (16)
H3A	0.0617	0.8110	0.0634	0.085*
C4	0.11734 (16)	0.6380 (9)	0.1050 (4)	0.0564 (13)
C5	0.13208 (17)	0.5982 (9)	0.0124 (4)	0.0574 (13)
H5A	0.1154	0.6568	−0.0386	0.069*
C6	0.17069 (17)	0.4744 (8)	−0.0067 (3)	0.0527 (12)
H6A	0.1799	0.4552	−0.0701	0.063*
C7	0.19647 (15)	0.3765 (8)	0.0666 (3)	0.0463 (11)
C8	0.18179 (17)	0.4124 (8)	0.1606 (3)	0.0525 (13)
C9	0.14295 (17)	0.5418 (9)	0.1772 (4)	0.0574 (13)
H9A	0.1338	0.5645	0.2404	0.069*
C10	0.23686 (16)	0.2213 (8)	0.0425 (3)	0.0480 (11)
C11	0.26936 (15)	0.2185 (8)	0.1322 (3)	0.0492 (11)
H11A	0.2772	0.3707	0.1440	0.059*
C12	0.24209 (17)	0.1469 (9)	0.2209 (3)	0.0560 (13)
H12A	0.2265	0.0108	0.2079	0.067*
H12B	0.2632	0.1252	0.2744	0.067*
C13	0.20670 (18)	0.3184 (11)	0.2463 (3)	0.0711 (16)
H13A	0.1839	0.2558	0.2895	0.085*
H13B	0.2222	0.4346	0.2805	0.085*
C14	0.26495 (17)	0.3094 (9)	−0.0430 (3)	0.0589 (13)
H14A	0.2462	0.3009	−0.1007	0.071*
H14B	0.2722	0.4606	−0.0317	0.071*
C15	0.30964 (17)	0.1850 (10)	−0.0586 (3)	0.0646 (14)
H15A	0.3024	0.0354	−0.0737	0.077*
H15B	0.3262	0.2463	−0.1129	0.077*
C16	0.34032 (18)	0.1924 (10)	0.0290 (3)	0.0631 (14)
H16A	0.3496	0.3412	0.0406	0.076*
H16B	0.3682	0.1091	0.0165	0.076*
C17	0.31646 (17)	0.1025 (7)	0.1202 (3)	0.0487 (11)
C18	0.21533 (19)	0.0064 (8)	0.0147 (4)	0.0611 (14)
H18A	0.1982	−0.0505	0.0682	0.092*
H18B	0.2394	−0.0936	−0.0029	0.092*
H18C	0.1948	0.0272	−0.0388	0.092*
C19	0.3132 (2)	−0.1455 (8)	0.1193 (4)	0.0704 (15)
H19A	0.3437	−0.2060	0.1118	0.106*
H19B	0.2939	−0.1909	0.0668	0.106*
H19C	0.2999	−0.1948	0.1787	0.106*
C20	0.34771 (18)	0.1739 (10)	0.2020 (4)	0.0627 (14)
C21	0.43576 (18)	−0.0547 (9)	0.3230 (4)	0.0562 (13)
C22	0.4184 (2)	−0.2817 (10)	0.3171 (5)	0.0831 (19)
H22A	0.3926	−0.2881	0.2734	0.125*
H22B	0.4085	−0.3287	0.3796	0.125*
H22C	0.4428	−0.3745	0.2945	0.125*
C23	0.47602 (16)	−0.0019 (9)	0.3849 (3)	0.0551 (12)
C24	0.4921 (2)	−0.1439 (10)	0.4542 (4)	0.0766 (17)
H24A	0.4777	−0.2780	0.4605	0.092*
C25	0.5287 (2)	−0.0937 (11)	0.5145 (4)	0.0809 (19)
H25A	0.5389	−0.1922	0.5604	0.097*
C26	0.54968 (19)	0.1069 (11)	0.5048 (4)	0.0647 (15)
C27	0.53477 (18)	0.2524 (11)	0.4368 (4)	0.0698 (16)
H27A	0.5491	0.3868	0.4314	0.084*
C28	0.49870 (18)	0.1988 (9)	0.3768 (4)	0.0653 (14)
H28A	0.4891	0.2968	0.3301	0.078*

	U11	U22	U33	U12	U13	U23
Cl	0.0746 (9)	0.1184 (14)	0.0778 (10)	−0.0015 (10)	−0.0227 (8)	0.0008 (10)
N	0.069 (3)	0.072 (3)	0.095 (4)	−0.004 (3)	−0.039 (3)	−0.005 (3)
O1	0.080 (3)	0.081 (3)	0.113 (3)	0.019 (2)	−0.041 (3)	−0.049 (3)
C1	0.094 (5)	0.082 (5)	0.253 (11)	0.014 (5)	0.004 (6)	−0.073 (7)
O2	0.070 (2)	0.062 (2)	0.099 (3)	0.011 (2)	−0.036 (2)	−0.017 (2)
C2	0.069 (4)	0.109 (6)	0.139 (6)	0.014 (4)	0.026 (4)	0.023 (5)
C3	0.064 (3)	0.067 (4)	0.080 (4)	0.011 (3)	0.000 (3)	0.003 (3)
C4	0.050 (3)	0.062 (3)	0.057 (3)	−0.001 (3)	−0.004 (2)	−0.004 (3)
C5	0.054 (3)	0.064 (3)	0.054 (3)	0.001 (3)	−0.014 (2)	0.000 (3)
C6	0.060 (3)	0.059 (3)	0.039 (3)	0.003 (3)	−0.006 (2)	−0.005 (2)
C7	0.045 (2)	0.054 (3)	0.040 (3)	−0.001 (2)	−0.0046 (19)	−0.003 (2)
C8	0.052 (3)	0.066 (3)	0.040 (3)	0.011 (3)	−0.003 (2)	0.003 (2)
C9	0.056 (3)	0.073 (3)	0.044 (3)	0.001 (3)	0.001 (2)	−0.004 (3)
C10	0.055 (3)	0.052 (3)	0.038 (2)	−0.007 (2)	0.000 (2)	−0.002 (2)
C11	0.047 (2)	0.055 (3)	0.046 (3)	−0.003 (2)	−0.003 (2)	0.001 (2)
C12	0.062 (3)	0.059 (3)	0.046 (3)	0.005 (3)	−0.003 (2)	0.009 (2)
C13	0.071 (3)	0.099 (4)	0.044 (3)	0.021 (4)	0.006 (3)	0.009 (3)
C14	0.063 (3)	0.074 (3)	0.040 (3)	−0.002 (3)	0.001 (2)	0.005 (3)
C15	0.060 (3)	0.074 (4)	0.059 (3)	0.005 (3)	0.014 (3)	0.001 (3)
C16	0.057 (3)	0.070 (3)	0.063 (3)	−0.001 (3)	0.005 (3)	−0.007 (3)
C17	0.050 (3)	0.042 (3)	0.054 (3)	−0.006 (2)	−0.006 (2)	−0.005 (2)
C18	0.071 (3)	0.049 (3)	0.063 (3)	−0.013 (3)	−0.011 (3)	−0.008 (2)
C19	0.079 (4)	0.043 (3)	0.089 (4)	−0.002 (3)	−0.015 (3)	−0.010 (3)
C20	0.055 (3)	0.067 (4)	0.065 (3)	0.007 (3)	−0.009 (3)	−0.006 (3)
C21	0.055 (3)	0.062 (3)	0.052 (3)	0.002 (3)	0.000 (2)	0.001 (3)
C22	0.079 (4)	0.071 (4)	0.099 (5)	−0.021 (3)	−0.014 (3)	0.027 (3)
C23	0.049 (3)	0.064 (3)	0.053 (3)	0.004 (3)	0.004 (2)	0.003 (3)
C24	0.086 (4)	0.070 (4)	0.074 (4)	0.005 (4)	−0.017 (3)	0.012 (3)
C25	0.091 (5)	0.077 (4)	0.075 (4)	0.009 (4)	−0.025 (4)	0.015 (3)
C26	0.058 (3)	0.084 (4)	0.052 (3)	0.011 (3)	−0.003 (3)	0.002 (3)
C27	0.053 (3)	0.082 (4)	0.074 (4)	−0.011 (3)	−0.008 (3)	0.004 (3)
C28	0.061 (3)	0.065 (3)	0.070 (3)	−0.004 (3)	−0.008 (3)	0.020 (3)

Cl—C26	1.717 (6)	C13—H13A	0.9700
N—C21	1.284 (7)	C13—H13B	0.9700
N—O2	1.441 (5)	C14—C15	1.515 (7)
O1—C20	1.218 (6)	C14—H14A	0.9700
C1—C3	1.549 (9)	C14—H14B	0.9700
C1—H1A	0.9600	C15—C16	1.507 (7)
C1—H1B	0.9600	C15—H15A	0.9700
C1—H1C	0.9600	C15—H15B	0.9700
O2—C20	1.348 (6)	C16—C17	1.547 (7)
C2—C3	1.493 (8)	C16—H16A	0.9700
C2—H2A	0.9600	C16—H16B	0.9700
C2—H2B	0.9600	C17—C20	1.517 (7)
C2—H2C	0.9600	C17—C19	1.535 (6)
C3—C4	1.497 (7)	C18—H18A	0.9600
C3—H3A	0.9800	C18—H18B	0.9600
C4—C5	1.379 (7)	C18—H18C	0.9600
C4—C9	1.381 (7)	C19—H19A	0.9600
C5—C6	1.376 (7)	C19—H19B	0.9600
C5—H5A	0.9300	C19—H19C	0.9600
C6—C7	1.399 (6)	C21—C23	1.481 (7)
C6—H6A	0.9300	C21—C22	1.491 (8)
C7—C8	1.393 (6)	C22—H22A	0.9600
C7—C10	1.544 (7)	C22—H22B	0.9600
C8—C9	1.394 (7)	C22—H22C	0.9600
C8—C13	1.509 (6)	C23—C24	1.383 (7)
C9—H9A	0.9300	C23—C28	1.406 (7)
C10—C18	1.515 (7)	C24—C25	1.383 (8)
C10—C14	1.538 (6)	C24—H24A	0.9300
C10—C11	1.561 (6)	C25—C26	1.385 (9)
C11—C12	1.528 (6)	C25—H25A	0.9300
C11—C17	1.543 (7)	C26—C27	1.374 (8)
C11—H11A	0.9800	C27—C28	1.374 (7)
C12—C13	1.512 (7)	C27—H27A	0.9300
C12—H12A	0.9700	C28—H28A	0.9300
C12—H12B	0.9700
C21—N—O2	108.6 (5)	C10—C14—H14A	109.2
C3—C1—H1A	109.5	C15—C14—H14B	109.2
C3—C1—H1B	109.5	C10—C14—H14B	109.2
H1A—C1—H1B	109.5	H14A—C14—H14B	107.9
C3—C1—H1C	109.5	C16—C15—C14	111.5 (4)
H1A—C1—H1C	109.5	C16—C15—H15A	109.3
H1B—C1—H1C	109.5	C14—C15—H15A	109.3
C20—O2—N	113.6 (4)	C16—C15—H15B	109.3
C3—C2—H2A	109.5	C14—C15—H15B	109.3
C3—C2—H2B	109.5	H15A—C15—H15B	108.0
H2A—C2—H2B	109.5	C15—C16—C17	113.1 (4)
C3—C2—H2C	109.5	C15—C16—H16A	108.9
H2A—C2—H2C	109.5	C17—C16—H16A	108.9
H2B—C2—H2C	109.5	C15—C16—H16B	108.9
C2—C3—C4	113.2 (5)	C17—C16—H16B	108.9
C2—C3—C1	112.0 (6)	H16A—C16—H16B	107.8
C4—C3—C1	111.0 (5)	C20—C17—C19	109.5 (4)
C2—C3—H3A	106.7	C20—C17—C11	107.8 (4)
C4—C3—H3A	106.7	C19—C17—C11	114.2 (4)
C1—C3—H3A	106.7	C20—C17—C16	104.4 (4)
C5—C4—C9	116.1 (5)	C19—C17—C16	112.2 (4)
C5—C4—C3	121.9 (5)	C11—C17—C16	108.2 (4)
C9—C4—C3	122.0 (5)	C10—C18—H18A	109.5
C6—C5—C4	121.9 (5)	C10—C18—H18B	109.5
C6—C5—H5A	119.0	H18A—C18—H18B	109.5
C4—C5—H5A	119.0	C10—C18—H18C	109.5
C5—C6—C7	121.9 (5)	H18A—C18—H18C	109.5
C5—C6—H6A	119.0	H18B—C18—H18C	109.5
C7—C6—H6A	119.0	C17—C19—H19A	109.5
C8—C7—C6	117.1 (4)	C17—C19—H19B	109.5
C8—C7—C10	122.1 (4)	H19A—C19—H19B	109.5
C6—C7—C10	120.7 (4)	C17—C19—H19C	109.5
C7—C8—C9	119.4 (4)	H19A—C19—H19C	109.5
C7—C8—C13	122.5 (4)	H19B—C19—H19C	109.5
C9—C8—C13	118.1 (4)	O1—C20—O2	122.3 (5)
C4—C9—C8	123.7 (5)	O1—C20—C17	127.2 (5)
C4—C9—H9A	118.2	O2—C20—C17	110.4 (5)
C8—C9—H9A	118.2	N—C21—C23	114.6 (5)
C18—C10—C14	109.1 (4)	N—C21—C22	125.3 (5)
C18—C10—C7	106.9 (4)	C23—C21—C22	120.2 (5)
C14—C10—C7	110.2 (4)	C21—C22—H22A	109.5
C18—C10—C11	116.1 (4)	C21—C22—H22B	109.5
C14—C10—C11	107.9 (4)	H22A—C22—H22B	109.5
C7—C10—C11	106.5 (3)	C21—C22—H22C	109.5
C12—C11—C17	113.9 (4)	H22A—C22—H22C	109.5
C12—C11—C10	109.9 (4)	H22B—C22—H22C	109.5
C17—C11—C10	116.5 (4)	C24—C23—C28	117.4 (5)
C12—C11—H11A	105.1	C24—C23—C21	121.9 (5)
C17—C11—H11A	105.1	C28—C23—C21	120.8 (5)
C10—C11—H11A	105.1	C25—C24—C23	122.4 (6)
C13—C12—C11	109.5 (4)	C25—C24—H24A	118.8
C13—C12—H12A	109.8	C23—C24—H24A	118.8
C11—C12—H12A	109.8	C24—C25—C26	118.3 (6)
C13—C12—H12B	109.8	C24—C25—H25A	120.8
C11—C12—H12B	109.8	C26—C25—H25A	120.8
H12A—C12—H12B	108.2	C27—C26—C25	121.0 (5)
C8—C13—C12	113.9 (4)	C27—C26—Cl	120.1 (5)
C8—C13—H13A	108.8	C25—C26—Cl	118.8 (5)
C12—C13—H13A	108.8	C28—C27—C26	119.9 (6)
C8—C13—H13B	108.8	C28—C27—H27A	120.1
C12—C13—H13B	108.8	C26—C27—H27A	120.1
H13A—C13—H13B	107.7	C27—C28—C23	121.0 (5)
C15—C14—C10	112.2 (4)	C27—C28—H28A	119.5
C15—C14—H14A	109.2	C23—C28—H28A	119.5
C21—N—O2—C20	148.1 (5)	C11—C10—C14—C15	54.1 (5)
C2—C3—C4—C5	118.1 (6)	C10—C14—C15—C16	−58.8 (6)
C1—C3—C4—C5	−115.0 (7)	C14—C15—C16—C17	57.7 (6)
C2—C3—C4—C9	−59.0 (7)	C12—C11—C17—C20	−67.0 (5)
C1—C3—C4—C9	68.0 (8)	C10—C11—C17—C20	163.4 (4)
C9—C4—C5—C6	−1.6 (7)	C12—C11—C17—C19	54.9 (6)
C3—C4—C5—C6	−178.8 (5)	C10—C11—C17—C19	−74.7 (5)
C4—C5—C6—C7	1.9 (8)	C12—C11—C17—C16	−179.3 (4)
C5—C6—C7—C8	−1.0 (7)	C10—C11—C17—C16	51.1 (5)
C5—C6—C7—C10	174.3 (4)	C15—C16—C17—C20	−166.7 (5)
C6—C7—C8—C9	−0.1 (7)	C15—C16—C17—C19	74.9 (6)
C10—C7—C8—C9	−175.3 (4)	C15—C16—C17—C11	−52.1 (6)
C6—C7—C8—C13	−179.4 (5)	N—O2—C20—O1	−9.4 (8)
C10—C7—C8—C13	5.4 (8)	N—O2—C20—C17	168.2 (4)
C5—C4—C9—C8	0.5 (8)	C19—C17—C20—O1	−147.7 (6)
C3—C4—C9—C8	177.7 (5)	C11—C17—C20—O1	−23.0 (8)
C7—C8—C9—C4	0.3 (8)	C16—C17—C20—O1	91.9 (7)
C13—C8—C9—C4	179.6 (5)	C19—C17—C20—O2	34.8 (6)
C8—C7—C10—C18	97.1 (5)	C11—C17—C20—O2	159.5 (4)
C6—C7—C10—C18	−77.9 (5)	C16—C17—C20—O2	−85.6 (5)
C8—C7—C10—C14	−144.4 (5)	O2—N—C21—C23	175.4 (4)
C6—C7—C10—C14	40.6 (6)	O2—N—C21—C22	−4.5 (8)
C8—C7—C10—C11	−27.6 (6)	N—C21—C23—C24	165.3 (5)
C6—C7—C10—C11	157.4 (4)	C22—C21—C23—C24	−14.8 (8)
C18—C10—C11—C12	−61.1 (5)	N—C21—C23—C28	−13.0 (7)
C14—C10—C11—C12	176.1 (4)	C22—C21—C23—C28	167.0 (5)
C7—C10—C11—C12	57.8 (5)	C28—C23—C24—C25	0.4 (8)
C18—C10—C11—C17	70.3 (5)	C21—C23—C24—C25	−177.9 (5)
C14—C10—C11—C17	−52.5 (5)	C23—C24—C25—C26	0.3 (9)
C7—C10—C11—C17	−170.8 (4)	C24—C25—C26—C27	−0.3 (9)
C17—C11—C12—C13	159.6 (4)	C24—C25—C26—Cl	177.3 (5)
C10—C11—C12—C13	−67.6 (5)	C25—C26—C27—C28	−0.5 (9)
C7—C8—C13—C12	−12.1 (8)	Cl—C26—C27—C28	−178.0 (4)
C9—C8—C13—C12	168.6 (5)	C26—C27—C28—C23	1.2 (8)
C11—C12—C13—C8	42.0 (6)	C24—C23—C28—C27	−1.2 (8)
C18—C10—C14—C15	−72.9 (5)	C21—C23—C28—C27	177.1 (5)
C7—C10—C14—C15	170.0 (4)