1-(2-Chloro-acet-yl)-3-methyl-2,6-bis-(3,4,5-trimethoxy-phen-yl)piperidine-4-one.

In the crystal structure of the title compound, C(26)H(32)ClNO(8), the piperidine ring is in a twist-chair conformation, with puckering parameters Q = 0.655 (4) Å, θ = 93.1 (1) and ϕ = 254.4 (3)°. The ortho C atoms of the piperidine ring deviate from the plane defined by the remaining ring atoms by 0.380 (3) and -0.250 (3) Å.

Related literature

For the biological and pharmacological properties of piperidines, see: Prostakov & Gaivoronskaya (1978 ▶). For the biological activity of piperidones with aryl substituents at the 2 and 6 positions, see: Mobio et al. (1989 ▶); Ganellin & Spickett (1965 ▶). For ring-puckering analysis, see: Cremer & Pople (1975 ▶). For the synthesis, see: Baliah et al. (1983 ▶).

Experimental

Crystal data

C26H32ClNO8

M = 521.98

Orthorhombic,

a = 13.8720 (8) Å

b = 16.5110 (11) Å

c = 22.8120 (16) Å

V = 5224.9 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.20 mm−1

T = 293 K

0.30 × 0.27 × 0.25 mm

Data collection

MacScience DIPLabo 32001 diffractometer

Absorption correction: none

8214 measured reflections

4464 independent reflections

3146 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.186

S = 1.05

4464 reflections

332 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.39 e Å−3

Data collection: XPRESS (MacScience, 2002 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015864/nc2143sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015864/nc2143Isup2.hkl

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

C26H32ClNO8	F(000) = 2208
Mr = 521.98	Dx = 1.327 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8214 reflections
a = 13.8720 (8) Å	θ = 2.9–25.0°
b = 16.5110 (11) Å	µ = 0.20 mm−1
c = 22.8120 (16) Å	T = 293 K
V = 5224.9 (6) Å3	Block, white
Z = 8	0.30 × 0.27 × 0.25 mm

MacScience DIPLabo 32001 diffractometer	3146 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
graphite	θmax = 25.0°, θmin = 2.9°
Detector resolution: 10.0 pixels mm-1	h = −16→16
ω scans	k = −19→19
8214 measured reflections	l = −27→26
4464 independent reflections

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0931P)2 + 2.926P] where P = (Fo2 + 2Fc2)/3
4464 reflections	(Δ/σ)max < 0.001
332 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Cl12	0.14569 (9)	−0.00580 (6)	0.36264 (6)	0.1014 (5)
O7	0.0245 (3)	−0.4484 (3)	0.28056 (17)	0.1467 (19)
O10	0.07651 (19)	−0.14395 (16)	0.42507 (10)	0.0742 (9)
O19	0.49642 (15)	−0.28235 (15)	0.40351 (9)	0.0623 (8)
O21	0.57332 (13)	−0.19912 (15)	0.31391 (9)	0.0584 (8)
O23	0.46432 (15)	−0.15115 (15)	0.22323 (9)	0.0595 (8)
O31	0.27178 (17)	−0.31372 (15)	0.56956 (9)	0.0649 (8)
O33	0.26328 (19)	−0.47563 (15)	0.57353 (9)	0.0725 (9)
O35	0.1596 (2)	−0.55902 (15)	0.49519 (11)	0.0847 (10)
N1	0.12281 (16)	−0.24570 (15)	0.36489 (10)	0.0473 (8)
C2	0.0590 (2)	−0.3025 (2)	0.39713 (13)	0.0524 (10)
C3	−0.0007 (3)	−0.3497 (2)	0.35294 (16)	0.0690 (14)
C4	0.0569 (3)	−0.3931 (2)	0.30853 (16)	0.0760 (16)
C5	0.1608 (3)	−0.3656 (2)	0.30122 (14)	0.0603 (11)
C6	0.1732 (2)	−0.27421 (18)	0.31092 (12)	0.0476 (10)
C8	0.2024 (4)	−0.3910 (3)	0.24254 (19)	0.0953 (19)
C9	0.1181 (2)	−0.1667 (2)	0.38063 (14)	0.0537 (11)
C11	0.1658 (3)	−0.10579 (19)	0.34041 (16)	0.0613 (12)
C13	0.2804 (2)	−0.25428 (18)	0.31204 (12)	0.0447 (9)
C14	0.3213 (2)	−0.21277 (19)	0.26566 (12)	0.0488 (10)
C15	0.4183 (2)	−0.19340 (19)	0.26646 (12)	0.0485 (10)
C16	0.4755 (2)	−0.21760 (19)	0.31333 (13)	0.0497 (10)
C17	0.4349 (2)	−0.26141 (19)	0.35897 (12)	0.0482 (10)
C18	0.3374 (2)	−0.27934 (18)	0.35895 (12)	0.0466 (9)
C20	0.4600 (3)	−0.3312 (2)	0.44945 (14)	0.0661 (11)
C22	0.5942 (2)	−0.1200 (2)	0.33503 (18)	0.0742 (14)
C24	0.4061 (3)	−0.1076 (2)	0.18305 (15)	0.0661 (11)
C25	0.1140 (2)	−0.3524 (2)	0.44265 (13)	0.0507 (10)
C26	0.1100 (2)	−0.4354 (2)	0.44530 (14)	0.0576 (11)
C27	0.1605 (3)	−0.4770 (2)	0.48873 (14)	0.0593 (11)
C28	0.2159 (2)	−0.4349 (2)	0.52945 (12)	0.0551 (11)
C29	0.2184 (2)	−0.3514 (2)	0.52730 (12)	0.0520 (10)
C30	0.1675 (2)	−0.3100 (2)	0.48416 (13)	0.0521 (10)
C32	0.2524 (3)	−0.2308 (2)	0.58099 (17)	0.0713 (12)
C34	0.3539 (3)	−0.5089 (3)	0.55613 (19)	0.0890 (17)
C36	0.1045 (4)	−0.6052 (2)	0.4561 (2)	0.0960 (18)
H2	0.01350	−0.26880	0.41910	0.0630*
H3A	−0.04010	−0.38860	0.37390	0.0830*
H3B	−0.04380	−0.31240	0.33310	0.0830*
H5	0.19860	−0.39300	0.33160	0.0720*
H6	0.14450	−0.24620	0.27730	0.0570*
H8A	0.18970	−0.44750	0.23610	0.1420*
H8B	0.27080	−0.38190	0.24250	0.1420*
H8C	0.17310	−0.35970	0.21190	0.1420*
H11A	0.14120	−0.11290	0.30100	0.0740*
H11B	0.23470	−0.11600	0.33950	0.0740*
H14	0.28350	−0.19780	0.23380	0.0590*
H18	0.31020	−0.30790	0.39000	0.0560*
H20A	0.40750	−0.30360	0.46830	0.0990*
H20B	0.51010	−0.34130	0.47750	0.0990*
H20C	0.43750	−0.38170	0.43370	0.0990*
H22A	0.56350	−0.08060	0.31040	0.1120*
H22B	0.66270	−0.11150	0.33460	0.1120*
H22C	0.57060	−0.11460	0.37440	0.1120*
H24A	0.37270	−0.14500	0.15800	0.0990*
H24B	0.44600	−0.07280	0.15970	0.0990*
H24C	0.36010	−0.07550	0.20420	0.0990*
H26	0.07340	−0.46390	0.41810	0.0690*
H30	0.16930	−0.25370	0.48300	0.0630*
H32A	0.27190	−0.19880	0.54790	0.1070*
H32B	0.28760	−0.21390	0.61510	0.1070*
H32C	0.18460	−0.22360	0.58770	0.1070*
H34A	0.34540	−0.54120	0.52150	0.1340*
H34B	0.37900	−0.54200	0.58710	0.1340*
H34C	0.39830	−0.46570	0.54800	0.1340*
H36A	0.03760	−0.59130	0.46030	0.1440*
H36B	0.11310	−0.66170	0.46460	0.1440*
H36C	0.12490	−0.59440	0.41670	0.1440*

	U11	U22	U33	U12	U13	U23
Cl12	0.1112 (9)	0.0590 (6)	0.1341 (10)	−0.0100 (6)	0.0317 (8)	−0.0153 (6)
O7	0.159 (3)	0.153 (4)	0.128 (3)	−0.093 (3)	0.024 (3)	−0.062 (3)
O10	0.0898 (18)	0.0728 (17)	0.0599 (14)	0.0103 (14)	0.0180 (14)	0.0001 (12)
O19	0.0498 (12)	0.0887 (18)	0.0483 (12)	0.0076 (11)	−0.0098 (10)	0.0087 (11)
O21	0.0394 (11)	0.0803 (16)	0.0554 (12)	0.0056 (10)	0.0030 (10)	−0.0077 (11)
O23	0.0507 (12)	0.0819 (16)	0.0460 (11)	0.0024 (11)	0.0044 (10)	0.0106 (11)
O31	0.0698 (14)	0.0686 (15)	0.0563 (13)	0.0078 (12)	−0.0193 (12)	−0.0053 (11)
O33	0.0930 (18)	0.0727 (16)	0.0519 (12)	0.0264 (14)	−0.0143 (12)	0.0041 (11)
O35	0.123 (2)	0.0532 (15)	0.0780 (17)	0.0040 (14)	−0.0279 (16)	0.0027 (13)
N1	0.0439 (13)	0.0544 (15)	0.0437 (13)	−0.0017 (11)	−0.0038 (11)	0.0064 (11)
C2	0.0450 (16)	0.065 (2)	0.0471 (17)	−0.0039 (14)	−0.0004 (14)	0.0133 (14)
C3	0.0561 (19)	0.082 (3)	0.069 (2)	−0.0179 (18)	−0.0134 (18)	0.0181 (19)
C4	0.091 (3)	0.078 (3)	0.059 (2)	−0.032 (2)	−0.010 (2)	−0.0022 (19)
C5	0.074 (2)	0.059 (2)	0.0480 (17)	−0.0071 (16)	−0.0056 (16)	−0.0033 (15)
C6	0.0459 (16)	0.0573 (19)	0.0395 (14)	−0.0012 (13)	−0.0030 (13)	0.0037 (13)
C8	0.122 (4)	0.084 (3)	0.080 (3)	−0.014 (3)	0.013 (3)	−0.028 (2)
C9	0.0534 (18)	0.059 (2)	0.0488 (17)	0.0052 (14)	−0.0093 (15)	0.0025 (15)
C11	0.063 (2)	0.053 (2)	0.068 (2)	−0.0030 (15)	0.0041 (17)	0.0006 (16)
C13	0.0458 (15)	0.0477 (16)	0.0405 (14)	0.0050 (13)	−0.0035 (13)	−0.0027 (12)
C14	0.0482 (16)	0.0592 (19)	0.0391 (15)	0.0065 (13)	−0.0035 (13)	0.0010 (13)
C15	0.0464 (16)	0.0610 (19)	0.0382 (15)	0.0056 (14)	0.0041 (13)	−0.0047 (13)
C16	0.0434 (16)	0.0617 (19)	0.0440 (16)	0.0083 (13)	0.0020 (13)	−0.0080 (14)
C17	0.0460 (16)	0.0606 (19)	0.0381 (15)	0.0123 (14)	−0.0033 (13)	−0.0044 (13)
C18	0.0491 (16)	0.0526 (18)	0.0382 (14)	0.0045 (13)	−0.0007 (13)	0.0010 (13)
C20	0.074 (2)	0.072 (2)	0.0524 (19)	0.0114 (18)	−0.0165 (18)	0.0106 (17)
C22	0.0535 (19)	0.091 (3)	0.078 (2)	−0.0043 (19)	0.0008 (19)	−0.019 (2)
C24	0.065 (2)	0.078 (2)	0.0553 (19)	0.0018 (18)	0.0036 (17)	0.0149 (17)
C25	0.0483 (16)	0.060 (2)	0.0438 (16)	−0.0018 (14)	−0.0009 (14)	0.0072 (14)
C26	0.066 (2)	0.058 (2)	0.0489 (17)	−0.0037 (16)	−0.0071 (16)	0.0021 (15)
C27	0.075 (2)	0.0498 (19)	0.0531 (18)	0.0052 (16)	−0.0015 (17)	0.0044 (15)
C28	0.066 (2)	0.059 (2)	0.0404 (15)	0.0137 (16)	−0.0069 (15)	0.0030 (14)
C29	0.0525 (17)	0.061 (2)	0.0424 (16)	0.0044 (14)	−0.0017 (14)	−0.0024 (14)
C30	0.0540 (17)	0.0533 (18)	0.0491 (16)	0.0016 (14)	−0.0026 (15)	0.0063 (14)
C32	0.080 (2)	0.064 (2)	0.070 (2)	−0.0091 (18)	−0.011 (2)	−0.0067 (18)
C34	0.096 (3)	0.085 (3)	0.086 (3)	0.038 (2)	−0.026 (2)	−0.012 (2)
C36	0.147 (4)	0.056 (2)	0.085 (3)	−0.007 (3)	−0.022 (3)	−0.010 (2)

Cl12—C11	1.749 (3)	C27—C28	1.392 (5)
O7—C4	1.201 (6)	C28—C29	1.380 (5)
O10—C9	1.225 (4)	C29—C30	1.391 (4)
O19—C17	1.371 (3)	C2—H2	0.9800
O19—C20	1.416 (4)	C3—H3A	0.9700
O21—C16	1.391 (3)	C3—H3B	0.9700
O21—C22	1.422 (4)	C5—H5	0.9800
O23—C15	1.366 (4)	C6—H6	0.9800
O23—C24	1.418 (4)	C8—H8A	0.9600
O31—C29	1.366 (4)	C8—H8B	0.9600
O31—C32	1.419 (4)	C8—H8C	0.9600
O33—C28	1.377 (4)	C11—H11A	0.9700
O33—C34	1.428 (5)	C11—H11B	0.9700
O35—C27	1.362 (4)	C14—H14	0.9300
O35—C36	1.400 (5)	C18—H18	0.9300
N1—C2	1.485 (4)	C20—H20A	0.9600
N1—C6	1.492 (4)	C20—H20B	0.9600
N1—C9	1.355 (4)	C20—H20C	0.9600
C2—C3	1.520 (5)	C22—H22A	0.9600
C2—C25	1.529 (4)	C22—H22B	0.9600
C3—C4	1.476 (5)	C22—H22C	0.9600
C4—C5	1.520 (6)	C24—H24A	0.9600
C5—C6	1.535 (4)	C24—H24B	0.9600
C5—C8	1.517 (6)	C24—H24C	0.9600
C6—C13	1.523 (4)	C26—H26	0.9300
C9—C11	1.514 (5)	C30—H30	0.9300
C13—C14	1.382 (4)	C32—H32A	0.9600
C13—C18	1.393 (4)	C32—H32B	0.9600
C14—C15	1.383 (4)	C32—H32C	0.9600
C15—C16	1.390 (4)	C34—H34A	0.9600
C16—C17	1.387 (4)	C34—H34B	0.9600
C17—C18	1.385 (4)	C34—H34C	0.9600
C25—C26	1.373 (5)	C36—H36A	0.9600
C25—C30	1.392 (4)	C36—H36B	0.9600
C26—C27	1.394 (5)	C36—H36C	0.9600
C17—O19—C20	118.0 (3)	C4—C5—H5	107.00
C16—O21—C22	113.8 (2)	C6—C5—H5	107.00
C15—O23—C24	117.4 (2)	C8—C5—H5	107.00
C29—O31—C32	117.8 (3)	N1—C6—H6	108.00
C28—O33—C34	113.9 (3)	C5—C6—H6	108.00
C27—O35—C36	118.5 (3)	C13—C6—H6	108.00
C2—N1—C6	119.3 (2)	C5—C8—H8A	109.00
C2—N1—C9	116.6 (2)	C5—C8—H8B	109.00
C6—N1—C9	123.0 (2)	C5—C8—H8C	109.00
N1—C2—C3	108.7 (2)	H8A—C8—H8B	109.00
N1—C2—C25	112.3 (2)	H8A—C8—H8C	110.00
C3—C2—C25	116.5 (3)	H8B—C8—H8C	109.00
C2—C3—C4	114.2 (3)	Cl12—C11—H11A	109.00
O7—C4—C3	122.1 (4)	Cl12—C11—H11B	109.00
O7—C4—C5	121.6 (4)	C9—C11—H11A	109.00
C3—C4—C5	116.3 (3)	C9—C11—H11B	109.00
C4—C5—C6	112.6 (3)	H11A—C11—H11B	108.00
C4—C5—C8	112.0 (3)	C13—C14—H14	120.00
C6—C5—C8	110.9 (3)	C15—C14—H14	120.00
N1—C6—C5	112.1 (2)	C13—C18—H18	120.00
N1—C6—C13	112.1 (2)	C17—C18—H18	120.00
C5—C6—C13	108.9 (3)	O19—C20—H20A	109.00
O10—C9—N1	122.5 (3)	O19—C20—H20B	110.00
O10—C9—C11	120.2 (3)	O19—C20—H20C	109.00
N1—C9—C11	117.3 (3)	H20A—C20—H20B	109.00
Cl12—C11—C9	112.4 (3)	H20A—C20—H20C	109.00
C6—C13—C14	119.7 (2)	H20B—C20—H20C	110.00
C6—C13—C18	120.2 (2)	O21—C22—H22A	110.00
C14—C13—C18	120.1 (3)	O21—C22—H22B	109.00
C13—C14—C15	120.3 (3)	O21—C22—H22C	109.00
O23—C15—C14	124.3 (3)	H22A—C22—H22B	110.00
O23—C15—C16	115.8 (2)	H22A—C22—H22C	109.00
C14—C15—C16	119.9 (3)	H22B—C22—H22C	109.00
O21—C16—C15	120.1 (3)	O23—C24—H24A	109.00
O21—C16—C17	120.2 (3)	O23—C24—H24B	110.00
C15—C16—C17	119.7 (3)	O23—C24—H24C	110.00
O19—C17—C16	115.8 (2)	H24A—C24—H24B	109.00
O19—C17—C18	123.7 (3)	H24A—C24—H24C	109.00
C16—C17—C18	120.5 (3)	H24B—C24—H24C	109.00
C13—C18—C17	119.4 (3)	C25—C26—H26	120.00
C2—C25—C26	123.2 (3)	C27—C26—H26	120.00
C2—C25—C30	117.2 (3)	C25—C30—H30	120.00
C26—C25—C30	119.6 (3)	C29—C30—H30	120.00
C25—C26—C27	120.2 (3)	O31—C32—H32A	109.00
O35—C27—C26	124.2 (3)	O31—C32—H32B	109.00
O35—C27—C28	115.4 (3)	O31—C32—H32C	110.00
C26—C27—C28	120.4 (3)	H32A—C32—H32B	110.00
O33—C28—C27	120.5 (3)	H32A—C32—H32C	109.00
O33—C28—C29	120.1 (3)	H32B—C32—H32C	109.00
C27—C28—C29	119.3 (3)	O33—C34—H34A	110.00
O31—C29—C28	116.3 (3)	O33—C34—H34B	110.00
O31—C29—C30	123.4 (3)	O33—C34—H34C	109.00
C28—C29—C30	120.2 (3)	H34A—C34—H34B	110.00
C25—C30—C29	120.3 (3)	H34A—C34—H34C	109.00
N1—C2—H2	106.00	H34B—C34—H34C	109.00
C3—C2—H2	106.00	O35—C36—H36A	109.00
C25—C2—H2	106.00	O35—C36—H36B	109.00
C2—C3—H3A	109.00	O35—C36—H36C	110.00
C2—C3—H3B	109.00	H36A—C36—H36B	109.00
C4—C3—H3A	109.00	H36A—C36—H36C	110.00
C4—C3—H3B	109.00	H36B—C36—H36C	109.00
H3A—C3—H3B	108.00
C20—O19—C17—C18	5.9 (4)	C4—C5—C6—C13	171.4 (3)
C20—O19—C17—C16	−176.3 (3)	C5—C6—C13—C18	−69.9 (3)
C22—O21—C16—C17	−97.6 (3)	N1—C6—C13—C18	54.7 (4)
C22—O21—C16—C15	83.5 (4)	N1—C6—C13—C14	−126.7 (3)
C24—O23—C15—C14	16.4 (4)	C5—C6—C13—C14	108.6 (3)
C24—O23—C15—C16	−163.9 (3)	N1—C9—C11—Cl12	175.0 (2)
C32—O31—C29—C30	19.2 (4)	O10—C9—C11—Cl12	−4.3 (4)
C32—O31—C29—C28	−160.1 (3)	C6—C13—C18—C17	179.4 (3)
C34—O33—C28—C29	−100.9 (4)	C18—C13—C14—C15	−2.3 (5)
C34—O33—C28—C27	82.9 (4)	C14—C13—C18—C17	0.8 (4)
C36—O35—C27—C28	179.3 (3)	C6—C13—C14—C15	179.2 (3)
C36—O35—C27—C26	−0.2 (5)	C13—C14—C15—C16	1.7 (5)
C9—N1—C2—C25	−103.5 (3)	C13—C14—C15—O23	−178.6 (3)
C6—N1—C9—C11	0.7 (4)	O23—C15—C16—O21	−0.6 (4)
C2—N1—C6—C5	−7.8 (3)	O23—C15—C16—C17	−179.5 (3)
C2—N1—C9—O10	11.9 (4)	C14—C15—C16—O21	179.2 (3)
C9—N1—C2—C3	126.2 (3)	C14—C15—C16—C17	0.3 (5)
C6—N1—C2—C3	−42.4 (3)	C15—C16—C17—O19	−179.6 (3)
C2—N1—C9—C11	−167.4 (3)	C15—C16—C17—C18	−1.7 (5)
C6—N1—C9—O10	−180.0 (3)	O21—C16—C17—C18	179.4 (3)
C9—N1—C6—C5	−175.6 (3)	O21—C16—C17—O19	1.5 (4)
C6—N1—C2—C25	88.0 (3)	O19—C17—C18—C13	178.9 (3)
C9—N1—C6—C13	61.6 (3)	C16—C17—C18—C13	1.2 (4)
C2—N1—C6—C13	−130.7 (3)	C2—C25—C30—C29	179.2 (3)
C3—C2—C25—C26	−1.1 (4)	C30—C25—C26—C27	−1.0 (5)
C3—C2—C25—C30	−178.8 (3)	C26—C25—C30—C29	1.4 (4)
N1—C2—C3—C4	55.7 (4)	C2—C25—C26—C27	−178.7 (3)
N1—C2—C25—C26	−127.3 (3)	C25—C26—C27—C28	−0.5 (5)
C25—C2—C3—C4	−72.3 (4)	C25—C26—C27—O35	179.0 (3)
N1—C2—C25—C30	55.0 (3)	O35—C27—C28—O33	−1.7 (5)
C2—C3—C4—C5	−17.8 (4)	O35—C27—C28—C29	−177.9 (3)
C2—C3—C4—O7	160.5 (4)	C26—C27—C28—C29	1.6 (5)
C3—C4—C5—C8	−159.8 (3)	C26—C27—C28—O33	177.9 (3)
O7—C4—C5—C6	147.7 (4)	O33—C28—C29—O31	1.8 (4)
C3—C4—C5—C6	−34.0 (4)	C27—C28—C29—C30	−1.2 (4)
O7—C4—C5—C8	21.9 (5)	O33—C28—C29—C30	−177.5 (3)
C8—C5—C6—C13	−62.2 (4)	C27—C28—C29—O31	178.1 (3)
C8—C5—C6—N1	173.2 (3)	O31—C29—C30—C25	−179.6 (3)
C4—C5—C6—N1	46.8 (3)	C28—C29—C30—C25	−0.3 (4)