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

In the title compound, C29H37NO3 {systematic name: (E)-1-(4-meth-oxy-phen-yl)ethanone O-[(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octa-hydro-phenanthrene-1-carbon-yl]oxime}, a new derivative of de-hydro-abietic acid, the two cyclo-hexane rings exhibit a trans-ring junction and are in chair and half-chair conformations. The C=N double bond exhibits an E conformation.

Related literature

For the biological activity of related compounds, see: Cui et al. (2013 ▶); Li et al. (2008 ▶); Rao et al. (2008 ▶); Sepulveda et al. (2005 ▶); For the crystal structures of a related compound, see: Rao et al. (2009 ▶).

Experimental

Crystal data

C29H37NO3

M = 447.60

Orthorhombic,

a = 6.1700 (12) Å

b = 11.051 (2) Å

c = 37.526 (8) Å

V = 2558.7 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (CAD-4 Software; North et al., 1968 ▶) T min = 0.978, T max = 0.993

5399 measured reflections

4691 independent reflections

2211 reflections with I > 2σ(I)

R int = 0.088

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.183

S = 1.00

4691 reflections

298 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

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/S1600536814016882/lr2129sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016882/lr2129Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S1600536814016882/lr2129fig1.tif

The mol­ecular structure of the title compound, hydrogen atoms are represented by small spheres of arbitrary radius and the displacement ellipsoids are at the 30% probability level.

CCDC reference: 1015316

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

C29H37NO3	F(000) = 968
Mr = 447.60	Dx = 1.162 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 6.1700 (12) Å	θ = 9–13°
b = 11.051 (2) Å	µ = 0.07 mm−1
c = 37.526 (8) Å	T = 293 K
V = 2558.7 (9) Å3	Block, white
Z = 4	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	2211 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.088
Graphite monochromator	θmax = 25.4°, θmin = 1.1°
ω/2θ scans	h = 0→7
Absorption correction: ψ scan (CAD-4 Software; North et al., 1968)	k = 0→13
Tmin = 0.978, Tmax = 0.993	l = −45→45
5399 measured reflections	3 standard reflections every 200 reflections
4691 independent reflections	intensity decay: 1%

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.183	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.060P)2] where P = (Fo2 + 2Fc2)/3
4691 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

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
N	0.1892 (7)	0.0800 (4)	0.03582 (11)	0.0798 (14)
O1	0.1751 (9)	−0.3034 (4)	−0.08665 (11)	0.1262 (18)
C1	0.3329 (16)	−0.3936 (6)	−0.0959 (2)	0.168 (4)
H1A	0.2748	−0.4457	−0.1140	0.252*
H1B	0.3680	−0.4407	−0.0751	0.252*
H1C	0.4616	−0.3549	−0.1047	0.252*
O2	0.2587 (6)	0.1742 (4)	0.06048 (9)	0.0806 (12)
C2	0.2309 (11)	−0.2209 (5)	−0.06054 (14)	0.0738 (16)
O3	−0.0806 (6)	0.1739 (4)	0.08121 (11)	0.1088 (16)
C3	0.4223 (10)	−0.2218 (5)	−0.04202 (14)	0.0784 (17)
H3A	0.5247	−0.2821	−0.0460	0.094*
C4	0.4604 (9)	−0.1316 (5)	−0.01735 (13)	0.0712 (16)
H4A	0.5918	−0.1306	−0.0052	0.085*
C5	0.3105 (8)	−0.0432 (5)	−0.01018 (12)	0.0590 (13)
C6	0.1146 (10)	−0.0433 (5)	−0.02848 (14)	0.0727 (16)
H6A	0.0097	0.0150	−0.0238	0.087*
C7	0.0789 (10)	−0.1324 (5)	−0.05395 (14)	0.0770 (16)
H7A	−0.0501	−0.1323	−0.0668	0.092*
C8	0.3520 (9)	0.0520 (6)	0.01648 (14)	0.0731 (16)
C9	0.5748 (10)	0.1086 (7)	0.01919 (18)	0.135 (3)
H9A	0.5759	0.1669	0.0381	0.202*
H9B	0.6099	0.1479	−0.0029	0.202*
H9C	0.6801	0.0468	0.0240	0.202*
C10	0.1024 (8)	0.2116 (5)	0.08260 (13)	0.0616 (13)
C11	0.1842 (8)	0.3063 (4)	0.10914 (12)	0.0548 (12)
C12	0.1060 (9)	0.4277 (5)	0.09359 (13)	0.0724 (16)
H12A	0.1925	0.4470	0.0728	0.087*
H12B	−0.0433	0.4191	0.0859	0.087*
C13	0.1212 (10)	0.5326 (4)	0.12026 (12)	0.0694 (15)
H13A	0.2719	0.5473	0.1262	0.083*
H13B	0.0627	0.6056	0.1096	0.083*
C14	−0.0049 (9)	0.5020 (4)	0.15382 (12)	0.0615 (14)
H14A	0.0084	0.5688	0.1704	0.074*
H14B	−0.1570	0.4940	0.1477	0.074*
C15	0.0682 (7)	0.3872 (4)	0.17213 (11)	0.0460 (11)
C16	0.0614 (7)	0.2829 (4)	0.14438 (11)	0.0501 (11)
H16A	−0.0913	0.2771	0.1374	0.060*
C17	−0.0814 (7)	0.3510 (4)	0.20262 (12)	0.0525 (12)
C18	−0.1403 (8)	0.2317 (5)	0.20981 (12)	0.0574 (13)
C19	−0.0723 (9)	0.1300 (4)	0.18619 (13)	0.0711 (15)
H19A	−0.1958	0.1046	0.1720	0.085*
H19B	−0.0292	0.0620	0.2009	0.085*
C20	0.1123 (8)	0.1615 (4)	0.16145 (13)	0.0659 (14)
H20A	0.1276	0.0998	0.1432	0.079*
H20B	0.2470	0.1664	0.1747	0.079*
C21	−0.1556 (9)	0.4395 (5)	0.22626 (13)	0.0650 (14)
H21A	−0.1182	0.5199	0.2222	0.078*
C22	−0.2828 (9)	0.4119 (5)	0.25553 (13)	0.0658 (14)
H22A	−0.3301	0.4733	0.2706	0.079*
C23	−0.3401 (9)	0.2922 (5)	0.26245 (13)	0.0623 (13)
C24	−0.2702 (9)	0.2063 (5)	0.23947 (13)	0.0696 (14)
H24A	−0.3104	0.1264	0.2436	0.084*
C25	0.4331 (8)	0.3015 (5)	0.11184 (15)	0.0794 (17)
H25A	0.4764	0.2251	0.1217	0.119*
H25B	0.4830	0.3658	0.1270	0.119*
H25C	0.4950	0.3106	0.0885	0.119*
C26	0.2970 (8)	0.4086 (4)	0.18935 (13)	0.0694 (15)
H26A	0.2883	0.4739	0.2062	0.104*
H26B	0.3996	0.4287	0.1710	0.104*
H26C	0.3430	0.3363	0.2013	0.104*
C27	−0.4765 (10)	0.2590 (5)	0.29540 (14)	0.0794 (17)
H27A	−0.4753	0.1706	0.2971	0.095*
C28	−0.3787 (12)	0.3065 (7)	0.32966 (14)	0.120 (3)
H28A	−0.4703	0.2851	0.3494	0.181*
H28B	−0.3660	0.3930	0.3283	0.181*
H28C	−0.2377	0.2716	0.3330	0.181*
C29	−0.7111 (11)	0.2963 (6)	0.29055 (18)	0.104 (2)
H29A	−0.7919	0.2758	0.3116	0.157*
H29B	−0.7712	0.2546	0.2704	0.157*
H29C	−0.7187	0.3820	0.2866	0.157*

	U11	U22	U33	U12	U13	U23
N	0.063 (3)	0.111 (4)	0.065 (3)	−0.009 (3)	0.001 (3)	−0.033 (3)
O1	0.185 (5)	0.093 (3)	0.101 (3)	0.023 (4)	−0.032 (4)	−0.031 (3)
C1	0.250 (11)	0.095 (5)	0.158 (7)	0.084 (7)	−0.017 (8)	−0.045 (5)
O2	0.063 (2)	0.115 (3)	0.064 (2)	−0.027 (2)	0.018 (2)	−0.035 (2)
C2	0.092 (4)	0.070 (4)	0.059 (3)	0.011 (4)	−0.003 (3)	0.000 (3)
O3	0.054 (2)	0.151 (4)	0.121 (3)	−0.029 (3)	0.003 (3)	−0.074 (3)
C3	0.094 (5)	0.074 (4)	0.067 (3)	0.024 (4)	0.005 (4)	0.006 (3)
C4	0.059 (3)	0.091 (4)	0.063 (3)	0.025 (3)	−0.006 (3)	−0.003 (3)
C5	0.052 (3)	0.077 (4)	0.048 (3)	0.000 (3)	−0.001 (3)	−0.003 (2)
C6	0.077 (4)	0.075 (4)	0.066 (3)	0.009 (3)	0.000 (3)	−0.012 (3)
C7	0.075 (4)	0.081 (4)	0.075 (4)	0.016 (4)	−0.011 (3)	−0.010 (3)
C8	0.058 (3)	0.112 (5)	0.049 (3)	−0.001 (3)	−0.001 (3)	−0.011 (3)
C9	0.062 (4)	0.216 (9)	0.127 (6)	−0.019 (5)	0.012 (4)	−0.075 (6)
C10	0.052 (3)	0.071 (3)	0.062 (3)	−0.003 (3)	0.002 (3)	−0.015 (3)
C11	0.040 (2)	0.072 (3)	0.053 (3)	−0.009 (3)	0.001 (2)	−0.014 (3)
C12	0.072 (4)	0.088 (4)	0.058 (3)	−0.017 (3)	−0.004 (3)	−0.002 (3)
C13	0.089 (4)	0.055 (3)	0.065 (3)	−0.005 (3)	0.014 (3)	0.006 (3)
C14	0.069 (3)	0.049 (3)	0.067 (3)	−0.005 (3)	0.007 (3)	−0.001 (2)
C15	0.045 (3)	0.040 (2)	0.053 (3)	−0.005 (2)	−0.005 (2)	0.003 (2)
C16	0.037 (3)	0.053 (3)	0.060 (3)	0.000 (2)	−0.005 (2)	−0.004 (2)
C17	0.049 (3)	0.053 (3)	0.055 (3)	0.006 (3)	−0.012 (2)	0.011 (2)
C18	0.050 (3)	0.074 (3)	0.049 (3)	0.003 (3)	−0.003 (2)	0.011 (2)
C19	0.077 (4)	0.063 (3)	0.073 (4)	−0.005 (3)	−0.004 (3)	0.000 (3)
C20	0.067 (4)	0.053 (3)	0.077 (3)	0.010 (3)	−0.009 (3)	−0.004 (3)
C21	0.068 (3)	0.065 (3)	0.062 (3)	0.004 (3)	−0.003 (3)	−0.005 (3)
C22	0.068 (3)	0.076 (3)	0.054 (3)	0.011 (3)	−0.004 (3)	−0.008 (3)
C23	0.065 (3)	0.067 (3)	0.055 (3)	−0.003 (3)	−0.003 (3)	0.008 (3)
C24	0.071 (4)	0.067 (3)	0.070 (3)	0.003 (3)	−0.007 (3)	0.010 (3)
C25	0.058 (3)	0.098 (4)	0.083 (4)	−0.013 (4)	−0.005 (3)	−0.008 (3)
C26	0.057 (3)	0.085 (4)	0.066 (3)	−0.026 (3)	−0.016 (3)	−0.008 (3)
C27	0.073 (4)	0.101 (4)	0.064 (4)	0.012 (4)	0.019 (3)	0.021 (3)
C28	0.136 (6)	0.166 (7)	0.059 (4)	0.012 (6)	0.003 (4)	0.011 (4)
C29	0.092 (5)	0.110 (5)	0.111 (5)	0.013 (4)	0.022 (4)	0.014 (4)

N—C8	1.277 (6)	C15—C17	1.523 (6)
N—O2	1.458 (5)	C15—C16	1.555 (5)
O1—C2	1.382 (6)	C15—C26	1.571 (6)
O1—C1	1.436 (7)	C16—C20	1.519 (6)
C1—H1A	0.9600	C16—H16A	0.9800
C1—H1B	0.9600	C17—C18	1.393 (6)
C1—H1C	0.9600	C17—C21	1.398 (6)
O2—C10	1.338 (5)	C18—C24	1.400 (6)
C2—C3	1.370 (8)	C18—C19	1.492 (6)
C2—C7	1.377 (7)	C19—C20	1.510 (6)
O3—C10	1.204 (5)	C19—H19A	0.9700
C3—C4	1.381 (7)	C19—H19B	0.9700
C3—H3A	0.9300	C20—H20A	0.9700
C4—C5	1.371 (6)	C20—H20B	0.9700
C4—H4A	0.9300	C21—C22	1.384 (6)
C5—C6	1.390 (7)	C21—H21A	0.9300
C5—C8	1.475 (7)	C22—C23	1.394 (6)
C6—C7	1.390 (7)	C22—H22A	0.9300
C6—H6A	0.9300	C23—C24	1.353 (6)
C7—H7A	0.9300	C23—C27	1.540 (7)
C8—C9	1.514 (8)	C24—H24A	0.9300
C9—H9A	0.9600	C25—H25A	0.9600
C9—H9B	0.9600	C25—H25B	0.9600
C9—H9C	0.9600	C25—H25C	0.9600
C10—C11	1.530 (6)	C26—H26A	0.9600
C11—C12	1.540 (6)	C26—H26B	0.9600
C11—C16	1.546 (6)	C26—H26C	0.9600
C11—C25	1.540 (6)	C27—C29	1.516 (8)
C12—C13	1.535 (6)	C27—C28	1.514 (8)
C12—H12A	0.9700	C27—H27A	0.9800
C12—H12B	0.9700	C28—H28A	0.9600
C13—C14	1.519 (6)	C28—H28B	0.9600
C13—H13A	0.9700	C28—H28C	0.9600
C13—H13B	0.9700	C29—H29A	0.9600
C14—C15	1.511 (6)	C29—H29B	0.9600
C14—H14A	0.9700	C29—H29C	0.9600
C14—H14B	0.9700
C8—N—O2	107.6 (4)	C16—C15—C26	114.3 (4)
C2—O1—C1	117.4 (6)	C20—C16—C11	114.0 (4)
O1—C1—H1A	109.5	C20—C16—C15	111.5 (3)
O1—C1—H1B	109.5	C11—C16—C15	115.8 (4)
H1A—C1—H1B	109.5	C20—C16—H16A	104.7
O1—C1—H1C	109.5	C11—C16—H16A	104.7
H1A—C1—H1C	109.5	C15—C16—H16A	104.7
H1B—C1—H1C	109.5	C18—C17—C21	117.0 (5)
C10—O2—N	113.7 (4)	C18—C17—C15	123.5 (4)
C3—C2—C7	120.1 (5)	C21—C17—C15	119.4 (4)
C3—C2—O1	124.7 (6)	C17—C18—C24	119.6 (5)
C7—C2—O1	115.2 (6)	C17—C18—C19	121.6 (4)
C2—C3—C4	118.7 (5)	C24—C18—C19	118.8 (5)
C2—C3—H3A	120.6	C18—C19—C20	113.8 (4)
C4—C3—H3A	120.6	C18—C19—H19A	108.8
C5—C4—C3	122.1 (5)	C20—C19—H19A	108.8
C5—C4—H4A	119.0	C18—C19—H19B	108.8
C3—C4—H4A	119.0	C20—C19—H19B	108.8
C4—C5—C6	119.3 (5)	H19A—C19—H19B	107.7
C4—C5—C8	121.6 (5)	C19—C20—C16	107.9 (4)
C6—C5—C8	119.1 (5)	C19—C20—H20A	110.1
C7—C6—C5	118.5 (5)	C16—C20—H20A	110.1
C7—C6—H6A	120.7	C19—C20—H20B	110.1
C5—C6—H6A	120.7	C16—C20—H20B	110.1
C2—C7—C6	121.2 (5)	H20A—C20—H20B	108.4
C2—C7—H7A	119.4	C22—C21—C17	122.3 (5)
C6—C7—H7A	119.4	C22—C21—H21A	118.8
N—C8—C5	114.9 (5)	C17—C21—H21A	118.8
N—C8—C9	125.2 (5)	C23—C22—C21	120.1 (5)
C5—C8—C9	119.9 (5)	C23—C22—H22A	120.0
C8—C9—H9A	109.5	C21—C22—H22A	120.0
C8—C9—H9B	109.5	C24—C23—C22	117.8 (5)
H9A—C9—H9B	109.5	C24—C23—C27	121.3 (5)
C8—C9—H9C	109.5	C22—C23—C27	120.9 (5)
H9A—C9—H9C	109.5	C23—C24—C18	123.2 (5)
H9B—C9—H9C	109.5	C23—C24—H24A	118.4
O3—C10—O2	122.8 (5)	C18—C24—H24A	118.4
O3—C10—C11	125.0 (5)	C11—C25—H25A	109.5
O2—C10—C11	112.2 (4)	C11—C25—H25B	109.5
C10—C11—C12	104.2 (4)	H25A—C25—H25B	109.5
C10—C11—C16	106.3 (4)	C11—C25—H25C	109.5
C12—C11—C16	108.5 (4)	H25A—C25—H25C	109.5
C10—C11—C25	110.4 (4)	H25B—C25—H25C	109.5
C12—C11—C25	111.5 (4)	C15—C26—H26A	109.5
C16—C11—C25	115.3 (4)	C15—C26—H26B	109.5
C13—C12—C11	113.1 (4)	H26A—C26—H26B	109.5
C13—C12—H12A	109.0	C15—C26—H26C	109.5
C11—C12—H12A	109.0	H26A—C26—H26C	109.5
C13—C12—H12B	109.0	H26B—C26—H26C	109.5
C11—C12—H12B	109.0	C29—C27—C28	112.9 (6)
H12A—C12—H12B	107.8	C29—C27—C23	111.1 (5)
C14—C13—C12	110.0 (4)	C28—C27—C23	112.4 (5)
C14—C13—H13A	109.7	C29—C27—H27A	106.6
C12—C13—H13A	109.7	C28—C27—H27A	106.6
C14—C13—H13B	109.7	C23—C27—H27A	106.6
C12—C13—H13B	109.7	C27—C28—H28A	109.5
H13A—C13—H13B	108.2	C27—C28—H28B	109.5
C15—C14—C13	114.3 (4)	H28A—C28—H28B	109.5
C15—C14—H14A	108.7	C27—C28—H28C	109.5
C13—C14—H14A	108.7	H28A—C28—H28C	109.5
C15—C14—H14B	108.7	H28B—C28—H28C	109.5
C13—C14—H14B	108.7	C27—C29—H29A	109.5
H14A—C14—H14B	107.6	C27—C29—H29B	109.5
C14—C15—C17	112.4 (4)	H29A—C29—H29B	109.5
C14—C15—C16	108.0 (3)	C27—C29—H29C	109.5
C17—C15—C16	107.0 (3)	H29A—C29—H29C	109.5
C14—C15—C26	109.2 (4)	H29B—C29—H29C	109.5
C17—C15—C26	106.0 (4)
C8—N—O2—C10	−179.7 (5)	C10—C11—C16—C15	−163.9 (4)
C1—O1—C2—C3	−2.5 (9)	C12—C11—C16—C15	−52.3 (5)
C1—O1—C2—C7	176.8 (6)	C25—C11—C16—C15	73.5 (5)
C7—C2—C3—C4	−1.2 (9)	C14—C15—C16—C20	−174.6 (4)
O1—C2—C3—C4	178.0 (5)	C17—C15—C16—C20	−53.4 (5)
C2—C3—C4—C5	1.8 (9)	C26—C15—C16—C20	63.6 (5)
C3—C4—C5—C6	−0.7 (8)	C14—C15—C16—C11	52.7 (5)
C3—C4—C5—C8	179.4 (5)	C17—C15—C16—C11	174.0 (4)
C4—C5—C6—C7	−1.0 (8)	C26—C15—C16—C11	−69.1 (5)
C8—C5—C6—C7	179.0 (5)	C14—C15—C17—C18	140.3 (4)
C3—C2—C7—C6	−0.4 (9)	C16—C15—C17—C18	21.9 (6)
O1—C2—C7—C6	−179.7 (5)	C26—C15—C17—C18	−100.4 (5)
C5—C6—C7—C2	1.5 (9)	C14—C15—C17—C21	−43.6 (6)
O2—N—C8—C5	179.8 (4)	C16—C15—C17—C21	−162.0 (4)
O2—N—C8—C9	−0.2 (9)	C26—C15—C17—C21	75.7 (5)
C4—C5—C8—N	−140.2 (6)	C21—C17—C18—C24	0.7 (6)
C6—C5—C8—N	39.9 (8)	C15—C17—C18—C24	176.9 (4)
C4—C5—C8—C9	39.9 (9)	C21—C17—C18—C19	179.3 (4)
C6—C5—C8—C9	−140.1 (6)	C15—C17—C18—C19	−4.4 (7)
N—O2—C10—O3	−2.7 (8)	C17—C18—C19—C20	16.9 (6)
N—O2—C10—C11	177.4 (4)	C24—C18—C19—C20	−164.4 (4)
O3—C10—C11—C12	−79.2 (7)	C18—C19—C20—C16	−46.7 (5)
O2—C10—C11—C12	100.7 (5)	C11—C16—C20—C19	−158.6 (4)
O3—C10—C11—C16	35.3 (8)	C15—C16—C20—C19	67.9 (5)
O2—C10—C11—C16	−144.8 (4)	C18—C17—C21—C22	−0.3 (7)
O3—C10—C11—C25	161.0 (6)	C15—C17—C21—C22	−176.7 (4)
O2—C10—C11—C25	−19.1 (6)	C17—C21—C22—C23	0.4 (8)
C10—C11—C12—C13	165.9 (4)	C21—C22—C23—C24	−1.0 (8)
C16—C11—C12—C13	53.0 (5)	C21—C22—C23—C27	178.4 (5)
C25—C11—C12—C13	−75.0 (6)	C22—C23—C24—C18	1.4 (8)
C11—C12—C13—C14	−56.2 (6)	C27—C23—C24—C18	−178.0 (5)
C12—C13—C14—C15	57.6 (6)	C17—C18—C24—C23	−1.3 (7)
C13—C14—C15—C17	−172.2 (4)	C19—C18—C24—C23	180.0 (5)
C13—C14—C15—C16	−54.5 (5)	C24—C23—C27—C29	−106.9 (6)
C13—C14—C15—C26	70.4 (5)	C22—C23—C27—C29	73.8 (7)
C10—C11—C16—C20	64.7 (5)	C24—C23—C27—C28	125.5 (6)
C12—C11—C16—C20	176.2 (4)	C22—C23—C27—C28	−53.8 (7)
C25—C11—C16—C20	−58.0 (6)