2',3'-Di­phenyl-4'-p-tolyl­spiro­[iso­thia­chroman-3,5'-isoxazolidin]-4(2H)-one

The title compound, C₃₀H₂₅NO₂S, contains an isoxazolidine ring in a twist conformation with the spiro-C [0.404 (2) Å] and the adjacent C atom [0.266 (2) Å] deviating from the plane of the remaining three atoms. The thia­pyran ring adopts a sofa conformation, with the five C atoms in a common plane (r.m.s.d. = 0.033 Å) and the S atom deviating by 0.984 (2) Å from this plane.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.099
• Data-to-parameter ratio = 13.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

The dipolar 1,3-cycloaddition reaction between alcenes and nitrones is an important method for producing isoxazolidines, which can be easily converted to different compounds, as reported in the literature (Gothelf & Jorgensen, 1994; Broggini & Zecchi, 1997; Coutouli-Argyropoulou et al., 1997). The present work is a contribution to these investigations, focusing on the dipole–dipolarophile approach in dipolar 1,3-cycloaddition reactions. The case in which the dipolarophilic site is inserted into different cyclic systems (Tshiamala et al., 1988; Kerbal et al., 1989; Filali Baba et al., 2000) or non-cyclic systems (Kerbal et al., 1988, 1991) has already been studied. After having explored the reaction between diphenylnitrilimines (DANI) and 3-arylidenisothiochroman-4-ones (Badri et al., 1999), we investigated the effects of the former on nitrones. In this case, the reaction is regiospecific and leads to spiro products. The synthesis of 2-arylideneisothiochroman-4-ones by condensation of para-substituted benzaldehyde with isothiochroman-4-one in an acidic medium has been accomplished according to reported procedures (Kerbal et al., 1990; Riahi et al., 1998) (see Scheme). Since NMR spectroscopy did not provide sufficient information about the nature of the reaction product we have carried out the X-ray structure analysis of the title compound, (I). The oxazolidine ring shows a twist conformation with C1 [0.404 (2) Å] and C5 [0.266 (2) Å] deviating from the plane of the remaining three atoms. The thiapyran ring adopts a sofa conformation, with the five C atoms in a common plane (r.m.s.d. = 0.033 Å) and the S atom deviating by 0.984 (2) Å from this plane.

S2. Experimental

The title compound was prepared according to Badri et al. (1999). Crystals were grown from an ethanol solution.

S3. Refinement

All H atoms were located by difference Fourier synthesis and refined with fixed individual displacement parameters [U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C_methyl)] using a riding model with tertiary C—H = 1.00 Å, secondary C—H = 0.99 Å, methyl C—H = 0.98 Å and aromatic C—H = 0.95 Å. The methyl group was allowed to rotate about its local threefold axes.

Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1991).

Figures

Fig. 1. A perspective view of the title compound with the atom-numbering scheme. Displacement ellipsoids are at the 50% probability level.

;

Crystal data

C30H25NO2S	Z = 2
Mr = 463.57	F(000) = 488
Triclinic, P1	Dx = 1.326 Mg m^−3
a = 9.6687 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2722 (3) Å	Cell parameters from 6557 reflections
c = 11.5579 (3) Å	θ = 1–25°
α = 78.850 (2)°	µ = 0.17 mm^−1
β = 73.486 (2)°	T = 173 K
γ = 75.860 (2)°	Block, colourless
V = 1160.66 (5) Å^3	0.41 × 0.36 × 0.18 mm

Data collection

Siemens CCD three-circle diffractometer	4250 independent reflections
Radiation source: fine-focus sealed tube	3575 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 25.4°, θmin = 1.9°
Absorption correction: empirical (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.934, Tmax = 0.970	k = −13→13
22101 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0414P)^2 + 0.6774P] where P = (Fo^2 + 2Fc^2)/3
4250 reflections	(Δ/σ)max = 0.010
308 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.18497 (5)	0.63967 (4)	0.30862 (4)	0.02792 (13)
C1	0.34960 (19)	0.68394 (16)	0.32057 (16)	0.0236 (4)
O2	0.39073 (13)	0.62759 (11)	0.43116 (11)	0.0259 (3)
N3	0.30182 (16)	0.70453 (13)	0.52489 (13)	0.0242 (3)
C4	0.24118 (19)	0.82587 (15)	0.46403 (15)	0.0234 (4)
H4	0.1338	0.8323	0.4726	0.028*
C5	0.32493 (19)	0.82168 (16)	0.32870 (15)	0.0236 (4)
H5	0.4238	0.8400	0.3199	0.028*
O6	0.56531 (15)	0.70614 (12)	0.16316 (12)	0.0372 (3)
C6	0.4810 (2)	0.63752 (17)	0.21676 (16)	0.0263 (4)
C7	0.5012 (2)	0.51196 (17)	0.18483 (16)	0.0282 (4)
C8	0.6290 (2)	0.47039 (19)	0.09726 (18)	0.0347 (5)
H8	0.6994	0.5216	0.0629	0.042*
C9	0.6543 (2)	0.3557 (2)	0.06009 (19)	0.0412 (5)
H9	0.7409	0.3287	0.0000	0.049*
C10	0.5525 (3)	0.2806 (2)	0.1111 (2)	0.0431 (5)
H10	0.5694	0.2018	0.0859	0.052*
C11	0.4258 (2)	0.31984 (18)	0.19874 (19)	0.0376 (5)
H11	0.3571	0.2672	0.2335	0.045*
C12	0.3980 (2)	0.43547 (17)	0.23656 (17)	0.0290 (4)
C13	0.2576 (2)	0.47501 (17)	0.32996 (17)	0.0308 (4)
H13A	0.2762	0.4510	0.4121	0.037*
H13B	0.1828	0.4307	0.3260	0.037*
C31	0.20415 (19)	0.64064 (16)	0.61646 (15)	0.0233 (4)
C32	0.0813 (2)	0.70767 (17)	0.69093 (16)	0.0277 (4)
H32	0.0597	0.7953	0.6760	0.033*
C33	−0.0094 (2)	0.64553 (18)	0.78708 (17)	0.0314 (4)
H33	−0.0930	0.6913	0.8373	0.038*
C34	0.0207 (2)	0.51815 (18)	0.81044 (17)	0.0325 (4)
H34	−0.0419	0.4763	0.8759	0.039*
C35	0.1432 (2)	0.45254 (17)	0.73722 (17)	0.0314 (4)
H35	0.1642	0.3650	0.7528	0.038*
C36	0.2362 (2)	0.51200 (16)	0.64142 (16)	0.0273 (4)
H36	0.3212	0.4655	0.5931	0.033*
C41	0.26170 (19)	0.93180 (16)	0.51707 (16)	0.0261 (4)
C42	0.3421 (2)	0.91200 (18)	0.60337 (18)	0.0340 (4)
H42	0.3852	0.8302	0.6316	0.041*
C43	0.3601 (3)	1.0112 (2)	0.6488 (2)	0.0428 (5)
H43	0.4147	0.9966	0.7086	0.051*
C44	0.2998 (2)	1.1302 (2)	0.6082 (2)	0.0432 (5)
H44	0.3140	1.1976	0.6388	0.052*
C45	0.2185 (2)	1.15132 (18)	0.5227 (2)	0.0399 (5)
H45	0.1760	1.2334	0.4948	0.048*
C46	0.1989 (2)	1.05301 (17)	0.47753 (18)	0.0330 (4)
H46	0.1422	1.0681	0.4192	0.040*
C51	0.25611 (19)	0.91426 (16)	0.23651 (16)	0.0241 (4)
C52	0.3438 (2)	0.98542 (17)	0.14762 (17)	0.0299 (4)
H52	0.4450	0.9743	0.1457	0.036*
C53	0.2864 (2)	1.07225 (18)	0.06184 (18)	0.0350 (5)
H53	0.3489	1.1197	0.0025	0.042*
C54	0.1398 (2)	1.09101 (17)	0.06109 (17)	0.0333 (4)
C541	0.0791 (3)	1.1854 (2)	−0.0336 (2)	0.0490 (6)
H54A	0.1071	1.2640	−0.0367	0.074*
H54B	−0.0285	1.1969	−0.0121	0.074*
H54C	0.1194	1.1564	−0.1134	0.074*
C55	0.0510 (2)	1.02117 (18)	0.15091 (18)	0.0328 (4)
H55	−0.0504	1.0332	0.1530	0.039*
C56	0.1077 (2)	0.93444 (17)	0.23737 (17)	0.0291 (4)
H56	0.0446	0.8883	0.2978	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0260 (2)	0.0264 (2)	0.0318 (3)	−0.00766 (18)	−0.00599 (19)	−0.00373 (19)
C1	0.0244 (9)	0.0228 (9)	0.0229 (9)	−0.0055 (7)	−0.0064 (7)	0.0003 (7)
O2	0.0277 (7)	0.0238 (6)	0.0220 (6)	−0.0001 (5)	−0.0046 (5)	−0.0021 (5)
N3	0.0274 (8)	0.0215 (7)	0.0215 (7)	−0.0029 (6)	−0.0040 (6)	−0.0032 (6)
C4	0.0235 (9)	0.0212 (9)	0.0237 (9)	−0.0041 (7)	−0.0062 (7)	0.0015 (7)
C5	0.0236 (9)	0.0231 (9)	0.0239 (9)	−0.0067 (7)	−0.0053 (7)	−0.0014 (7)
O6	0.0332 (8)	0.0318 (7)	0.0381 (8)	−0.0085 (6)	0.0040 (6)	−0.0016 (6)
C6	0.0257 (9)	0.0288 (10)	0.0228 (9)	−0.0051 (8)	−0.0079 (7)	0.0021 (7)
C7	0.0306 (10)	0.0303 (10)	0.0227 (9)	−0.0011 (8)	−0.0101 (8)	−0.0030 (8)
C8	0.0336 (11)	0.0391 (11)	0.0290 (10)	−0.0001 (9)	−0.0093 (8)	−0.0060 (9)
C9	0.0410 (12)	0.0443 (12)	0.0354 (11)	0.0083 (10)	−0.0118 (9)	−0.0164 (10)
C10	0.0547 (14)	0.0322 (11)	0.0444 (13)	0.0054 (10)	−0.0213 (11)	−0.0143 (10)
C11	0.0487 (13)	0.0297 (10)	0.0371 (11)	−0.0057 (9)	−0.0159 (10)	−0.0057 (9)
C12	0.0358 (11)	0.0268 (9)	0.0249 (9)	−0.0028 (8)	−0.0123 (8)	−0.0016 (8)
C13	0.0374 (11)	0.0262 (10)	0.0300 (10)	−0.0109 (8)	−0.0072 (8)	−0.0027 (8)
C31	0.0269 (9)	0.0243 (9)	0.0201 (8)	−0.0062 (7)	−0.0084 (7)	−0.0007 (7)
C32	0.0315 (10)	0.0238 (9)	0.0264 (9)	−0.0033 (8)	−0.0067 (8)	−0.0033 (7)
C33	0.0299 (10)	0.0331 (10)	0.0286 (10)	−0.0049 (8)	−0.0029 (8)	−0.0062 (8)
C34	0.0351 (11)	0.0331 (10)	0.0274 (10)	−0.0129 (9)	−0.0033 (8)	0.0018 (8)
C35	0.0399 (11)	0.0220 (9)	0.0298 (10)	−0.0065 (8)	−0.0085 (9)	0.0026 (8)
C36	0.0312 (10)	0.0250 (9)	0.0230 (9)	−0.0017 (8)	−0.0069 (8)	−0.0015 (7)
C41	0.0261 (9)	0.0253 (9)	0.0240 (9)	−0.0077 (7)	0.0002 (7)	−0.0028 (7)
C42	0.0401 (11)	0.0290 (10)	0.0345 (11)	−0.0087 (9)	−0.0095 (9)	−0.0052 (8)
C43	0.0474 (13)	0.0460 (13)	0.0432 (12)	−0.0168 (10)	−0.0122 (10)	−0.0140 (10)
C44	0.0456 (13)	0.0356 (12)	0.0492 (13)	−0.0182 (10)	0.0046 (10)	−0.0196 (10)
C45	0.0403 (12)	0.0236 (10)	0.0466 (13)	−0.0065 (9)	0.0048 (10)	−0.0063 (9)
C46	0.0333 (11)	0.0269 (10)	0.0339 (10)	−0.0041 (8)	−0.0034 (8)	−0.0025 (8)
C51	0.0265 (9)	0.0212 (9)	0.0227 (9)	−0.0045 (7)	−0.0044 (7)	−0.0017 (7)
C52	0.0289 (10)	0.0261 (9)	0.0309 (10)	−0.0065 (8)	−0.0027 (8)	−0.0004 (8)
C53	0.0430 (12)	0.0262 (10)	0.0276 (10)	−0.0087 (9)	0.0008 (9)	0.0037 (8)
C54	0.0448 (12)	0.0249 (10)	0.0266 (10)	−0.0020 (8)	−0.0090 (9)	−0.0009 (8)
C541	0.0675 (16)	0.0357 (12)	0.0378 (12)	−0.0016 (11)	−0.0186 (11)	0.0064 (10)
C55	0.0325 (10)	0.0304 (10)	0.0345 (11)	−0.0023 (8)	−0.0112 (9)	−0.0028 (8)
C56	0.0310 (10)	0.0267 (9)	0.0272 (10)	−0.0081 (8)	−0.0048 (8)	0.0017 (8)

Geometric parameters (Å, º)

S1—C13	1.8121 (19)	C33—C34	1.382 (3)
S1—C1	1.8280 (18)	C33—H33	0.9500
C1—O2	1.431 (2)	C34—C35	1.382 (3)
C1—C5	1.529 (2)	C34—H34	0.9500
C1—C6	1.542 (2)	C35—C36	1.387 (3)
O2—N3	1.4609 (18)	C35—H35	0.9500
N3—C31	1.414 (2)	C36—H36	0.9500
N3—C4	1.476 (2)	C41—C42	1.385 (3)
C4—C41	1.519 (2)	C41—C46	1.398 (3)
C4—C5	1.547 (2)	C42—C43	1.389 (3)
C4—H4	1.0000	C42—H42	0.9500
C5—C51	1.517 (2)	C43—C44	1.375 (3)
C5—H5	1.0000	C43—H43	0.9500
O6—C6	1.217 (2)	C44—C45	1.383 (3)
C6—C7	1.485 (3)	C44—H44	0.9500
C7—C8	1.400 (3)	C45—C46	1.386 (3)
C7—C12	1.406 (3)	C45—H45	0.9500
C8—C9	1.384 (3)	C46—H46	0.9500
C8—H8	0.9500	C51—C52	1.391 (2)
C9—C10	1.385 (3)	C51—C56	1.395 (3)
C9—H9	0.9500	C52—C53	1.386 (3)
C10—C11	1.388 (3)	C52—H52	0.9500
C10—H10	0.9500	C53—C54	1.384 (3)
C11—C12	1.395 (3)	C53—H53	0.9500
C11—H11	0.9500	C54—C55	1.394 (3)
C12—C13	1.504 (3)	C54—C541	1.511 (3)
C13—H13A	0.9900	C541—H54A	0.9800
C13—H13B	0.9900	C541—H54B	0.9800
C31—C36	1.397 (2)	C541—H54C	0.9800
C31—C32	1.398 (3)	C55—C56	1.388 (3)
C32—C33	1.392 (3)	C55—H55	0.9500
C32—H32	0.9500	C56—H56	0.9500
C13—S1—C1	95.14 (9)	C31—C32—H32	120.1
O2—C1—C5	102.58 (13)	C34—C33—C32	120.89 (18)
O2—C1—C6	105.77 (13)	C34—C33—H33	119.6
C5—C1—C6	114.28 (14)	C32—C33—H33	119.6
O2—C1—S1	112.35 (11)	C35—C34—C33	119.04 (17)
C5—C1—S1	112.42 (12)	C35—C34—H34	120.5
C6—C1—S1	109.14 (12)	C33—C34—H34	120.5
C1—O2—N3	106.71 (12)	C34—C35—C36	121.34 (17)
C31—N3—O2	111.65 (13)	C34—C35—H35	119.3
C31—N3—C4	118.55 (14)	C36—C35—H35	119.3
O2—N3—C4	108.29 (12)	C35—C36—C31	119.55 (17)
N3—C4—C41	111.96 (14)	C35—C36—H36	120.2
N3—C4—C5	103.40 (13)	C31—C36—H36	120.2
C41—C4—C5	113.42 (14)	C42—C41—C46	118.71 (18)
N3—C4—H4	109.3	C42—C41—C4	121.85 (16)
C41—C4—H4	109.3	C46—C41—C4	119.44 (17)
C5—C4—H4	109.3	C41—C42—C43	120.30 (19)
C51—C5—C1	118.84 (14)	C41—C42—H42	119.8
C51—C5—C4	116.23 (14)	C43—C42—H42	119.8
C1—C5—C4	100.87 (13)	C44—C43—C42	120.7 (2)
C51—C5—H5	106.7	C44—C43—H43	119.7
C1—C5—H5	106.7	C42—C43—H43	119.7
C4—C5—H5	106.7	C43—C44—C45	119.63 (19)
O6—C6—C7	121.99 (17)	C43—C44—H44	120.2
O6—C6—C1	118.35 (16)	C45—C44—H44	120.2
C7—C6—C1	119.65 (15)	C44—C45—C46	120.1 (2)
C8—C7—C12	119.47 (18)	C44—C45—H45	119.9
C8—C7—C6	117.28 (17)	C46—C45—H45	119.9
C12—C7—C6	123.24 (16)	C45—C46—C41	120.5 (2)
C9—C8—C7	120.9 (2)	C45—C46—H46	119.7
C9—C8—H8	119.6	C41—C46—H46	119.7
C7—C8—H8	119.6	C52—C51—C56	117.65 (16)
C8—C9—C10	119.5 (2)	C52—C51—C5	118.86 (16)
C8—C9—H9	120.2	C56—C51—C5	123.48 (15)
C10—C9—H9	120.2	C53—C52—C51	121.34 (18)
C9—C10—C11	120.4 (2)	C53—C52—H52	119.3
C9—C10—H10	119.8	C51—C52—H52	119.3
C11—C10—H10	119.8	C54—C53—C52	121.17 (18)
C10—C11—C12	120.8 (2)	C54—C53—H53	119.4
C10—C11—H11	119.6	C52—C53—H53	119.4
C12—C11—H11	119.6	C53—C54—C55	117.75 (17)
C11—C12—C7	118.89 (18)	C53—C54—C541	120.57 (19)
C11—C12—C13	118.91 (18)	C55—C54—C541	121.7 (2)
C7—C12—C13	122.19 (16)	C54—C541—H54A	109.5
C12—C13—S1	113.07 (13)	C54—C541—H54B	109.5
C12—C13—H13A	109.0	H54A—C541—H54B	109.5
S1—C13—H13A	109.0	C54—C541—H54C	109.5
C12—C13—H13B	109.0	H54A—C541—H54C	109.5
S1—C13—H13B	109.0	H54B—C541—H54C	109.5
H13A—C13—H13B	107.8	C56—C55—C54	121.32 (19)
C36—C31—C32	119.39 (16)	C56—C55—H55	119.3
C36—C31—N3	120.93 (16)	C54—C55—H55	119.3
C32—C31—N3	119.37 (15)	C55—C56—C51	120.76 (17)
C33—C32—C31	119.75 (17)	C55—C56—H56	119.6
C33—C32—H32	120.1	C51—C56—H56	119.6
C13—S1—C1—O2	−55.10 (13)	C6—C7—C12—C13	−0.3 (3)
C13—S1—C1—C5	−170.22 (13)	C11—C12—C13—S1	−146.76 (15)
C13—S1—C1—C6	61.89 (13)	C7—C12—C13—S1	32.3 (2)
C5—C1—O2—N3	37.30 (15)	C1—S1—C13—C12	−58.25 (15)
C6—C1—O2—N3	157.36 (13)	O2—N3—C31—C36	26.3 (2)
S1—C1—O2—N3	−83.66 (13)	C4—N3—C31—C36	153.17 (16)
C1—O2—N3—C31	115.14 (14)	O2—N3—C31—C32	−160.09 (15)
C1—O2—N3—C4	−17.14 (16)	C4—N3—C31—C32	−33.2 (2)
C31—N3—C4—C41	98.89 (17)	C36—C31—C32—C33	−1.5 (3)
O2—N3—C4—C41	−132.64 (14)	N3—C31—C32—C33	−175.22 (17)
C31—N3—C4—C5	−138.65 (15)	C31—C32—C33—C34	0.3 (3)
O2—N3—C4—C5	−10.18 (16)	C32—C33—C34—C35	0.4 (3)
O2—C1—C5—C51	−170.53 (14)	C33—C34—C35—C36	0.2 (3)
C6—C1—C5—C51	75.50 (19)	C34—C35—C36—C31	−1.4 (3)
S1—C1—C5—C51	−49.63 (19)	C32—C31—C36—C35	2.0 (3)
O2—C1—C5—C4	−42.25 (16)	N3—C31—C36—C35	175.67 (17)
C6—C1—C5—C4	−156.22 (14)	N3—C4—C41—C42	6.2 (2)
S1—C1—C5—C4	78.66 (14)	C5—C4—C41—C42	−110.35 (19)
N3—C4—C5—C51	161.43 (14)	N3—C4—C41—C46	−174.25 (15)
C41—C4—C5—C51	−77.09 (19)	C5—C4—C41—C46	69.2 (2)
N3—C4—C5—C1	31.48 (16)	C46—C41—C42—C43	−0.3 (3)
C41—C4—C5—C1	152.95 (15)	C4—C41—C42—C43	179.21 (18)
O2—C1—C6—O6	−101.43 (18)	C41—C42—C43—C44	−0.6 (3)
C5—C1—C6—O6	10.6 (2)	C42—C43—C44—C45	1.0 (3)
S1—C1—C6—O6	137.49 (15)	C43—C44—C45—C46	−0.5 (3)
O2—C1—C6—C7	78.72 (18)	C44—C45—C46—C41	−0.5 (3)
C5—C1—C6—C7	−169.20 (15)	C42—C41—C46—C45	0.9 (3)
S1—C1—C6—C7	−42.36 (19)	C4—C41—C46—C45	−178.69 (17)
O6—C6—C7—C8	5.6 (3)	C1—C5—C51—C52	−108.74 (19)
C1—C6—C7—C8	−174.59 (16)	C4—C5—C51—C52	130.51 (17)
O6—C6—C7—C12	−173.40 (18)	C1—C5—C51—C56	72.8 (2)
C1—C6—C7—C12	6.4 (3)	C4—C5—C51—C56	−48.0 (2)
C12—C7—C8—C9	0.7 (3)	C56—C51—C52—C53	−0.8 (3)
C6—C7—C8—C9	−178.31 (18)	C5—C51—C52—C53	−179.36 (17)
C7—C8—C9—C10	−0.6 (3)	C51—C52—C53—C54	−0.3 (3)
C8—C9—C10—C11	0.1 (3)	C52—C53—C54—C55	1.1 (3)
C9—C10—C11—C12	0.4 (3)	C52—C53—C54—C541	−179.55 (19)
C10—C11—C12—C7	−0.4 (3)	C53—C54—C55—C56	−0.9 (3)
C10—C11—C12—C13	178.74 (19)	C541—C54—C55—C56	179.84 (19)
C8—C7—C12—C11	−0.2 (3)	C54—C55—C56—C51	−0.3 (3)
C6—C7—C12—C11	178.76 (17)	C52—C51—C56—C55	1.1 (3)
C8—C7—C12—C13	−179.27 (17)	C5—C51—C56—C55	179.56 (17)